Pyridone compounds and agricultural and horticultural fungicides containing the same as active ingredients

Abstract

Pyridine compounds of Formula (1) are provided: ##STR00001##
wherein R1, R2, X, Y and Het are defined. The pyridine compounds can be used to treat or prevent plant diseases.

Claims

1. A compound represented by Formula (1) ##STR03670## or a salt thereof wherein R1 represents a C1-C6 alkyl group optionally substituted with one substituent A, a C1-C6 haloalkyl group, or RaRbN— wherein Ra and Rb each independently represents a hydrogen atom, a C1-C6 alkyl group optionally substituted with one substituent B, a C1-C6 haloalkyl group or a C3-C8 cycloalkyl group or Ra and Rb together with the nitrogen atom to which they are bonded form an aziridinyl group, an azetidinyl group, a pyrrolidinyl group, a piperidinyl group, a homopiperidinyl group or an azocanyl group; R2 represents a hydrogen atom, a halogen atom, a C1-C6 alkyl group optionally substituted with one substituent A, a C1-C6 haloalkyl group, a C2-C6 alkynyl group optionally substituted with one substituent A, a C1-C6 alkoxy group optionally substituted with one substituent A, or Rx1C(═O)— wherein Rx1 represents a hydrogen atom, a C1-C6 alkyl group optionally substituted with one substituent B, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C3-C8 cycloalkoxy group or RaRbN— wherein Ra and Rb are the same as defined hereinabove; Het represents a pyridyl group, a thienyl group, a pyrrolyl group, a pyrazolyl group, an imidazolyl group, a triazolyl group, a tetrazolyl group, an oxazolyl group or a 3 to 6-membered ring group containing 1 to 2 oxygen atoms, the pyridyl group is optionally substituted with 0 to 4 substituents R3 with the proviso that when two or more substituents R3 are present, each R3 represents an independent substituent, the thienyl group is optionally substituted with 0 to 3 substituents R3 with the proviso that when two or more substituents R3 are present, each R3 represents an independent substituent, the pyrrolyl group, the pyrazolyl group, the imidazolyl group, the triazolyl group or the tetrazolyl group is each independently and optionally substituted with 0 to 4 substituents R3 with the proviso that when two or more substituents R3 are present, each R3 represents an independent substituent, the oxazolyl group is optionally substituted with 0 to 2 substituents R3 with the proviso that when two substituents R3 are present, each R3 represents an independent substituent, R3 represents a cyano group, a nitro group, a halogen atom, a C1-C6 alkyl group optionally substituted with one substituent C, a C1-C6 haloalkyl group, a C1-C6 alkoxy group optionally substituted with one substituent C, RaRbN— wherein Ra and Rb each independently represents a hydrogen atom, a C1-C6 alkyl group optionally substituted with one substituent B, a C1-C6 haloalkyl group or a C3-C8 cycloalkyl group or Ra and Rb together with the nitrogen atom to which they are bonded form an aziridinyl group, an azetidinyl group, a pyrrolidinyl group, a piperidinyl group, a homopiperidinyl group or an azocanyl group, Rx1C(═O)— wherein Rx1 is the same as defined hereinabove, Rx2C(═O)N(Rx3)- wherein Rx2 represents a hydrogen atom, a C1-C6 alkyl group optionally substituted with one substituent B, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C3-C8 cycloalkoxy group or RaRbN— wherein Ra and Rb are the same as defined hereinabove, Rx3 represents a hydrogen atom, a C1-C6 alkyl group optionally substituted with one substituent B, a C1-C6 haloalkyl group or a C3-C8 cycloalkyl group; Y represents a phenyl group, the phenyl group is substituted with R4 at the ortho position and further optionally substituted with 0 to 4 substituents R5 with the proviso that when two or more substituents R5 are present, each R5 represents an independent substituent, R4 represents a cyano group, a nitro group, a halogen atom, a C1-C6 alkyl group optionally substituted with one substituent C, a C1-C6 haloalkyl group, or a C1-C6 alkoxy group optionally substituted with one substituent C, R5 represents a hydroxyl group, a cyano group, a halogen atom, a C1-C6 alkyl group optionally substituted with one substituent C, a C1-C6 alkoxy group optionally substituted with one substituent C, a C2-C6 alkenyloxy group optionally substituted with one substituent C, a C3-C6 alkynyloxy group optionally substituted with one substituent C, RaRbN— wherein Ra and Rb are the same as defined hereinabove, Rc-L- wherein Rc represents a C1-C6 alkyl group or a C1-C6 haloalkyl group and L represents S, SO or SO.sub.2, or Rx1C(═O)O— wherein Rx1 is the same as defined hereinabove; X represents an oxygen atom or a sulfur atom; a bond containing the broken line represents a double bond or a single bond; and the substituent A is at least one selected from the group consisting of a hydroxyl group, a cyano group, a C3-C8 cycloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C3-C8 cycloalkoxy group, RaRbN— wherein Ra and Rb are the same as defined hereinabove and Rc-L- wherein Rc and L are the same as defined hereinabove; the substituent B is at least one selected from the group consisting of a cyano group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group and a C3-C8 cycloalkoxy group; the substituent C is at least one selected from the group consisting of a hydroxyl group, a cyano group, a C3-C8 cycloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C3-C8 cycloalkoxy group, a C2-C6 alkoxyalkoxy group, RaRbN— wherein Ra and Rb are the same as defined hereinabove, Rc-L- wherein Rc and L are the same as defined hereinabove, Rx1C(═O)— wherein Rx1 is the same as defined hereinabove and a 3 to 6-membered ring group containing 1 to 2 oxygen atoms; the substituent D is at least one selected from the group consisting of a hydroxyl group, a cyano group, a nitro group, a halogen atom, a C1-C6 alkyl group which may be substituted with one substituent B, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group and a C3-C8 cycloalkoxy group.

2. A compound represented by Formula (2) ##STR03671## or a salt thereof wherein R2 represents a hydrogen atom, a halogen atom, a C1-C6 alkyl group optionally substituted with one substituent A, a C1-C6 haloalkyl group, a C2-C6 alkynyl group optionally substituted with one substituent A, a C1-C6 alkoxy group optionally substituted with one substituent A, or Rx1C(═O)— wherein Rx1 represents a hydrogen atom, a C1-C6 alkyl group optionally substituted with one substituent B, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C3-C8 cycloalkoxy group or RaRbN— wherein Ra and Rb each independently represents a hydrogen atom, a C1-C6 alkyl group optionally substituted with one substituent B, a C1-C6 haloalkyl group or a C3-C8 cycloalkyl group or Ra and Rb together with the nitrogen atom to which they are bonded form an aziridinyl group, an azetidinyl group, a pyrrolidinyl group, a piperidinyl group, a homopiperidinyl group or an azocanyl group; Het represents a pyridyl group, a thienyl group, a pyrrolyl group, a pyrazolyl group, an imidazolyl group, a triazolyl group, a tetrazolyl group, an oxazolyl group or a 3 to 6-membered ring group containing 1 to 2 oxygen atoms, the pyridyl group is optionally substituted with 0 to 4 substituents R3 with the proviso that when two or more substituents R3 are present, each R3 represents an independent substituent, the thienyl group is optionally substituted with 0 to 3 substituents R3 with the proviso that when two or more substituents R3 are present, each R3 represents an independent substituent, the pyrrolyl group, the pyrazolyl group, the triazolyl group or the tetrazolyl group is each independently and optionally substituted with 0 to 4 substituents R3 with the proviso that when two or more substituents R3 are present, each R3 represents an independent substituent, the imidazolyl group is substituted with 1 to 3 substituents R3 with the proviso that when two or more substituents R3 are present, each R3 represents an independent substituent, the oxazolyl group is optionally substituted with 0 to 2 substituents R3 with the proviso that when two substituents R3 are present, each R3 represents an independent substituent, R3 represents a cyano group, a nitro group, a halogen atom, a C1-C6 alkyl group optionally substituted with one substituent C, a C1-C6 haloalkyl group, a C1-C6 alkoxy group optionally substituted with one substituent C, RaRbN— wherein Ra and Rb each independently represents a hydrogen atom, a C1-C6 alkyl group optionally substituted with one substituent B, a C1-C6 haloalkyl group or a C3-C8 cycloalkyl group or Ra and Rb together with the nitrogen atom to which they are bonded form an aziridinyl group, an azetidinyl group, a pyrrolidinyl group, a piperidinyl group, a homopiperidinyl group or an azocanyl group, Rx1C(═O)— wherein Rx1 is the same as defined hereinabove, or Rx2C(═O)N(Rx3)- wherein Rx2 represents a hydrogen atom, a C1-C6 alkyl group optionally substituted with one substituent B, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C3-C8 cycloalkoxy group or RaRbN— wherein Ra and Rb are the same as defined hereinabove, Rx3 represents a hydrogen atom, a C1-C6 alkyl group optionally substituted with one substituent B, a C1-C6 haloalkyl group or a C3-C8 cycloalkyl group; Y represents a phenyl group, the phenyl group is substituted with R4 at the ortho position and further optionally substituted with 0 to 4 substituents R5 with the proviso that when two or more substituents R5 are present, each R5 represents an independent substituent, R4 represents a cyano group, a nitro group, a halogen atom, a C1-C6 alkyl group optionally substituted with one substituent C, a C1-C6 haloalkyl group, or a C1-C6 alkoxy group optionally substituted with one substituent C, R5 represents a hydroxyl group, a cyano group, a halogen atom, a C1-C6 alkyl group optionally substituted with one substituent C, a C1-C6 alkoxy group optionally substituted with one substituent C, a C2-C6 alkenyloxy group optionally substituted with one substituent C, a C3-C6 alkynyloxy group optionally substituted with one substituent C, RaRbN— wherein Ra and Rb are the same as defined hereinabove, Rc-L- wherein Rc represents a C1-C6 alkyl group or a C1-C6 haloalkyl group and L represents S, SO or SO.sub.2, or Rx1C(═O)O— wherein Rx1 is the same as defined hereinabove; X represents an oxygen atom or a sulfur atom; and the substituent is at least one selected from the group consisting of a hydroxyl group, a cyano group, a C3-C8 cycloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C3-C8 cycloalkoxy group, RaRbN— wherein Ra and Rb are the same as defined hereinabove) and Rc-L- wherein Rc and L are the same as defined hereinabove; the substituent B is at least one selected from the group consisting of a cyano group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group and a C3-C8 cycloalkoxy group; the substituent C is at least one selected from the group consisting of a hydroxyl group, a cyano group, a C3-C8 cycloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C3-C8 cycloalkoxy group, a C2-C6 alkoxyalkoxy group, RaRbN— wherein Ra and Rb are the same as defined hereinabove, Rc-L- wherein Rc and L are the same as defined hereinabove), Rx1C(═O)— wherein Rx1 is the same as defined hereinabove and a 3 to 6-membered ring group containing 1 to 2 oxygen atoms; and the substituent D is at least one selected from the group consisting of a hydroxyl group, a cyano group, a nitro group, a halogen atom, a C1-C6 alkyl group which may be substituted with one substituent B, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group and a C3-C8 cycloalkoxy group.

3. An agricultural and horticultural pest control agent containing the compound or a salt thereof according to claim 1 as an active ingredient.

4. An agricultural and horticultural fungicide containing the compound or a salt thereof according to claim 1 as an active ingredient.

5. A method for preventing and/or treating a plant disease, which comprises applying the agricultural and horticultural pest control agent according to claim 3 to a plant, a plant seed or a soil for plant cultivation.

6. A method for preventing and/or treating a plant disease, which comprises applying the agricultural and horticultural fungicides according to claim 4 to a plant, a plant seed or a soil for plant cultivation.

Description

DESCRIPTION OF EMBODIMENTS

(1) Hereinbelow, embodiments for carrying out the present invention will be described in detail.

(2) The terminologies used in the claims and the specification are understood in accordance with the definitions which are generally used in the art unless otherwise specified.

(3) In the present specification, the abbreviations used are explained below.

(4) DMF: N,N-dimethylformamide, THF: tetrahydrofuran, Me: methyl group, Et: ethyl group, Pr: propyl group, Bu: butyl group, Ac: acetyl group, Ph: phenyl group, Py: pyridyl group, Thio: thienyl group, Pyrrolyl: pyrrolyl group, Pyra: pyrazolyl group, Imida: imidazolyl group, Triazolyl: triazolyl group, Tetrazolyl: tetrazolyl group, Oxa: oxazolyl group, i: iso, sec: secondary, t: tertiary, ═: double bond and ≡: triple bond. In the columns in the tables, Pr and Bu used without any prefix indicate that the respective groups have a normal form.

(5) The definitions of the terminologies used in the present specification will be explained below.

(6) The expression Cx-Cy means that the number of carbon atoms that are possessed range from x to y. Here, x and y each represent an integer and are also understood to disclose all individual integers between x and y inclusive. For example, C1-C6 means that the number of carbon atoms that are possessed is 1, 2, 3, 4, 5 or 6; C2-C6 means that the number of carbon atoms that are possessed is 2, 3, 4, 5 or 6; C3-C8 means that the number of carbon atoms that are possessed is 3, 4, 5, 6, 7 or 8; C3-C6 means that the number of carbon atoms that are possessed is 3, 4, 5 or 6; and C1-C3 means that the number of carbon atoms that are possessed is 1, 2 or 3.

(7) The terms “optionally substituted” means it is to be substituted or unsubstituted. When this terms are used and a number of the substituent(s) is not clearly shown, the number of the substituent(s) indicates to be 1. On the other hand, for example, when a number of the substituent(s) is designated to as “optionally substituted with 0 to 6”, it is to be understood to disclose all individual integers between 0 to 6 inclusive. That is, it means that a number of substituent(s) is 0, 1, 2, 3, 4, 5 or 6. Similarly, “optionally substituted with 0 to 5” means that a number of substituent(s) is 0, 1, 2, 3, 4 or 5; “optionally substituted with 0 to 4” means that a number of substituent(s) is 0, 1, 2, 3 or 4; “optionally substituted with 0 to 3” means that a number of substituent(s) is 0, 1, 2 or 3; and “optionally substituted with 0 to 2” means that a number of substituent(s) of 0, 1 or 2.

(8) C1-C6 alkyl group may be a linear or branched and may include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a sec-butyl group, a t-butyl group, a pentyl group, an isopentyl group, a 2-methylbutyl group, a neopentyl group, a 1-ethylpropyl group, a hexyl group, a 4-methylpentyl group, a 3-methylpentyl group, a 2-methylpentyl group, a 1-methylpentyl group, a 3,3-dimethylbutyl group, a 2,2-dimethylbutyl group, a 1,1-dimethylbutyl group, a 1,2-dimethylbutyl group, a 1,3-dimethylbutyl group, a 2,3-dimethylbutyl group, a 2-ethylbutyl group, a 1-isopropylpropyl group, a 1,1,2-trimethylpropyl group, a, 1,2,2-trimethylpropyl group and the like.

(9) The halogen atom may include a fluorine atom, a chlorine atom, a bromine atom, an iodine atom and the like.

(10) The C1-C6 haloalkyl group represents a group resulting from the substitution of the above-mentioned C1l-C6 alkyl group with 1 or 2 or more halogen atoms in place of any hydrogen atom(s). When the group is substituted with two or more halogen atoms, these halogen atoms may be the same as or different from one another and the number of the substituents is not particularly limited as long as they can exist as a substituent. Specific examples of the C1-C6 haloalkyl group may include a monofluoromethyl group, a difluoromethyl group, a trifluoromethyl group, a monochloromethyl group, a monobromomethyl group, a monoiodomethyl group, a chlorodifluoromethyl group, a bromodifluoromethyl group, a 1-fluoroethyl group, a 2-fluoroethyl group, a 1,1-difluoroethyl group, a 2,2-difluoroethyl group, a 2,2,2-trifluoroethyl group, a 1,1,2,2-tetrafluoroethyl group, a pentafluoroethyl group, a 2,2,2-trichloroethyl group, a 3,3-difluoropropyl group, a 3,3,3-trifluoropropyl group, a heptafluoropropyl group, a heptafluoroisopropyl group, a 2,2,2-trifluoro-1-(trifluoromethyl)ethyl group, a nonafluorobutyl group, a nonafluoro-sec-butyl group, a 3,3,4,4,5,5,5-heptafluoropentyl group, a undecafluoropentyl group, a tridecafluorohexyl group and the like.

(11) The C3-C8 cycloalkyl group includes a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group and the like.

(12) The C2-C6 alkenyl group represents a linear or branched, unsaturated hydrocarbon group having 1 or 2 or more double bonds. When the group has geometric isomeric forms, the group may be either one of the E-isomer or the Z-isomer, or may be a mixture of the E-isomer and the Z-isomer in an appropriate ratio without limitation as long as the number of carbon atoms falls in the designated range. Specific examples of the C2-C6 alkenyl group may include a vinyl group, a 1-propenyl group, an allyl group, a 1-butenyl group, a 2-butenyl group, a 3-butenyl group, a 1-pentenyl group, a 2-pentenyl group, a 3-pentenyl group, a 4-pentenyl group, a 3-methyl-2-butenyl group, a 1-hexenyl group, a 2-hexenyl group, a 3-hexenyl group, a 4-hexenyl group, a 5-hexenyl group, a 4-methyl-3-pentenyl group, a 3-methyl-2-pentenyl group and the like.

(13) The C2-C6 haloalkenyl group represents a group resulting from the substitution of the above-mentioned C2-C6 alkenyl group with 1 or 2 or more halogen atoms in place of any hydrogen atom(s). When the group is substituted with two or more halogen atoms, these halogen atoms may be the same as or different from one another and the number of the substituents is not particularly limited as long as they can exist as a substituent. Specific examples of the C2-C6 haloalkenyl group may include a 2-fluorovinyl group, a 2,2-difluorovinyl group, a 2,2-dichlorovinyl group, a 3-fluoroallyl group, a 3,3-difluoroallyl group, a 3,3-dichloroallyl group, a 4,4-difluoro-3-butenyl group, a 5,5-difluoro-4-pentenyl group, a 6,6-difluoro-5-hexenyl group and the like.

(14) The C2-C6 alkynyl group represents a linear or branched, unsaturated hydrocarbon group having 1 or 2 or more triple bonds. Specific examples of the C2-C6 alkynyl group may include an ethynyl group, a 1-propynyl group, a propargyl group, a 1-butynyl group, a 2-butynyl group, a 3-butynyl group, a 1-pentynyl group, a 2-pentynyl group, a 3-pentynyl group, a 4-pentynyl group, a 1,1-dimethyl-2-propynyl group, a 1-hexynyl group, a 2-hexynyl group, a 3-hexynyl group, a 4-hexynyl group, a 5-hexynyl group and the like.

(15) The C2-C6 haloalkynyl group represents a group resulting from the substitution of the above-mentioned C2-C6 alkynyl group with 1 or 2 or more halogen atoms in place of any hydrogen atom(s). When the group is substituted with two or more halogen atoms, these halogen atoms may be the same as or different from one another and the number of the substituents is not particularly limited as long as they can exist as a substituent. Specific examples of the C2-C6 haloalkynyl group may include a 2-fluoroethynyl group, a 2-chloroethynyl group, a 2-bromoethynyl group, a 2-iodoethynyl group, a 3,3-difluoro-1-propynyl group, a 3-chloro-3,3-difluoro-1-propynyl group, a 3-bromo-3,3-difluoro-1-propynyl group, a 3,3,3-trifluoro-1-propynyl group, a 4,4-difluoro-1-butynyl group, a 4,4-difluoro-2-butynyl group, a 4-chloro-4,4-difluoro-1-butynyl group, a 4-chloro-4,4-difluoro-2-butynyl group, a 4-bromo-4,4-difluoro-1-butynyl group, a 4-bromo-4,4-difluoro-2-butynyl group, a 4,4,4-trifluoro-1-butynyl group, a 4,4,4-trifluoro-2-butynyl group, a 5,5-difluoro-3-pentynyl group, a 5-chloro-5,5-difluoro-3-pentynyl group, a 5-bromo-5,5-difluoro-3-pentynyl group, a 5,5,5-trifluoro-3-pentynyl group, a 6,6-difluoro-4-hexynyl group, a 6-chloro-6,6-difluoro-4-hexynyl group, a 6-bromo-6,6-difluoro-4-hexynyl group, a 6,6,6-trifluoro-4-hexynyl group and the like.

(16) The C1-C6 alkoxy group represents a combination of the above-mentioned C1-C6 alkyl group and an oxygen atom as a bonding site. Specific examples of the C1-C6 alkoxy group may include a methoxy group, an ethoxy group, a propyloxy group, an isopropyloxy group, a butoxy group, an isobutoxy group, a sec-butoxy group, a t-butoxy group, a pentyloxy group, an isopentyloxy group, a 1-methylbutoxy group, a 2-methylbutoxy group, a neopentyloxy group, a 1-ethylpropyloxy group, a 1,2-dimethylpropyloxy group, a hexyloxy group, a 1-methylpentyloxy group, a 2-methylpentyloxy group, a 3-methylpentyloxy group, a 4-methylpentyloxy group, a 1,1-dimethylbutoxy group, a 2,2-dimethylbutoxy group, a 3,3-dimethylbutoxy group, a 1,2-dimethylbutoxy group, a 1,3-dimethylbutoxy group, a 2,3-dimethylbutoxy group, a 2-ethylbutoxy group, a 1-isopropylpropyloxy group, a 1,1,2-trimethylpropyloxy group, a 1,2,2-trimethylpropyloxy group and the like.

(17) The C1-C6 haloalkoxy group represents a group resulting from the substitution of the above-mentioned C1-C6 alkoxy group with 1 or 2 or more halogen atoms in place of any hydrogen atom(s). When the group is substituted with two or more halogen atoms, these halogen atoms may be the same as or different from one another and the number of the substituents is not particularly limited as long as they can exist as a substituent. Specific examples of the C1-C6 haloalkoxy group may include a difluoromethoxy group, a trifluoromethoxy group, a chlorodifluoromethoxy group, a bromodifluoromethoxy group, a 2-fluoroethoxy group, a 2,2-difluoroethoxy group, a 2,2,2-trifluoroethoxy group, a 1,1,2,2-tetrafluoroethoxy group, a pentafluoroethoxy group, a 2,2,2-trichloroethoxy group, a 3,3-difluoropropyloxy group, a 3,3,3-trifluoropropyloxy group, a heptafluoropropyloxy group, a heptafluoroisopropyloxy group, a 2,2,2-trifluoro-1-(trifluoromethyl)-ethoxy group, a nonafluorobutoxy group, a nonafluoro-sec-butoxy group, a 3,3,4,4,5,5,5-heptafluoropentyloxy group, a undecafluoropentyloxy group, a tridecafluorohexyloxy group and the like.

(18) The C3-C8 cycloalkoxy group represents a combination of the above-mentioned C3-C8 cycloalkyl group and an oxygen atom as a bonding site. Specific examples of the C3-C8 cycloalkoxy group may include a cyclopropyloxy group, a cyclobutoxy group, a cyclopentyloxy group, a cyclohexyloxy group, a cycloheptyloxy group, a cyclooctyloxy group and the like.

(19) The C2-C6 alkenyloxy group represents a combination of the above-mentioned C2-C6 alkenyl group and an oxygen atom as a bonding site. When the group has geometric isomeric forms, the group may be either one of the E-isomer or the Z-isomer, or may be a mixture of the E-isomer and the Z-isomer in an appropriate ratio without limitation as long as the number of carbon atoms falls in the designated range. Specific examples of the C2-C6 alkenyloxy group may include a vinyloxy group, a 1-propenyloxy group, an allyloxy group, a 1-butenyloxy group, a 2-butenyloxy group, a 3-butenyloxy group, a 1-pentenyloxy group, a 2-pentenyloxy group, a 3-pentenyloxy group, a 4-pentenyloxy group, a 3-methyl-2-butenyloxy group, a 1-hexenyloxy group, a 2-hexenyloxy group, a 3-hexenyloxy group, a 4-hexenyloxy group, a 5-hexenyloxy group, a 4-methyl-3-pentenyloxy group, a 3-methyl-2-pentenyloxy group and the like.

(20) The C2-C6 haloalkenyloxy group represents a group resulting from the substitution of the above-mentioned C2-C6 alkenyloxy group with 1 or 2 or more halogen atoms in place of any hydrogen atom(s). When the group is substituted with two or more halogen atoms, these halogen atoms may be the same as or different from one another and the number of the substituents is not particularly limited as long as they can exist as a substituent. Specific examples of the C2-C6 haloalkenyloxy group may include a 2-fluorovinyloxy group, a 2,2-difluorovinyloxy group, a 2,2-dichlorovinyloxy group, a 3-fluoroallyloxy group, a 3,3-difluoroallyloxy group, a 3,3-dichloroallyloxy group, a 4,4-difluoro-3-butenyloxy group, a 5,5-difluoro-4-pentenyloxy group, a 6,6-difluoro-5-hexenyloxy group and the like.

(21) The C3-C6 alkynyloxy group represents a combination of a C3-C6 alkynyl group belonging to the above-mentioned C2-C6 alkynyl group, and an oxygen atom as a bonding site. Specific examples of the C3-C6 alkynyloxy group may include a propargyloxy group, a 2-butynyloxy group, a 3-butynyloxy group, a 2-pentynyloxy group, a 3-pentynyloxy group, a 4-pentynyloxy group, a 1,1-dimethyl-2-propynyloxy group, a 2-hexynyloxy group, a 3-hexynyloxy group, a 4-hexynyloxy group, a 5-hexynyloxy group and the like.

(22) The C3-C6 haloalkynyloxy group represents a group resulting from the substitution of the above-mentioned C3-C6 alkynyloxy group with 1 or 2 or more halogen atoms in place of any hydrogen atom(s). When the group is substituted with two or more halogen atoms, these halogen atoms may be the same as or different from one another and the number of the substituents is not particularly limited as long as they can exist as a substituent. Specific examples of the C3-C6 haloalkynyloxy group may include a 1,1-difluoro-2-propynyloxy group, a 4,4-difluoro-2-butynyloxy group, a 4-chloro-4,4-difluoro-2-butynyloxy group, a 4-bromo-4,4-difluoro-2-butynyloxy group, a 4,4,4-trifluoro-2-butynyloxy group, a 5,5-difluoro-3-pentynyloxy group, a 5-chloro-5,5-difluoro-3-pentynyloxy group, a 5-bromo-5,5-difluoro-3-pentynyloxy group, a 5,5,5-trifluoro-3-pentynyloxy group, a 6,6-difluoro-4-hexynyloxy group, a 6-chloro-6,6-difluoro-4-hexynyloxy group, a 6-bromo-6,6-difluoro-4-hexynyloxy group, a 6,6,6-trifluoro-4-hexynyloxy group and the like.

(23) The C2-C6 alkoxyalkoxy group represents a group resulting from the substitution of a C1-C5 alkoxy group belonging to the above-mentioned C1-C6 alkoxy group with 1 or 2 or more C1-C5 alkoxy groups in place of any hydrogen atom(s). It is not particularly limited as long as the total number of the carbon atoms is within the range of the designated number of the carbon atoms. Specific examples of the C2-C6 alkoxyalkoxy group may include a methoxymethoxy group, an ethoxymethoxy group, a propyloxymethoxy group, isopropyloxymethoxy group, a methoxyethoxy group, ethoxyethoxy group, a propyloxyethoxy group, isopropyloxyethoxy group, a methoxypropyloxy group, an ethoxypropyloxy group, a propyloxypropyloxy group, an isopropyloxypropyloxy group and the like.

(24) The aryl group represents a cyclic aromatic substituent constituted by a hydrogen atom(s) and a carbon atom(s). Specific examples of the aryl group may include a phenyl group, a naphthyl group and the like.

(25) The heteroaryl group represents a cyclic aromatic substituent containing at least one hetero atom selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom as a constitutional atom of the ring. Specific examples of the heteroaryl group may include a pyridyl group, a pyridazinyl group, a pyrimidinyl group, a pyrazinyl group, a triazinyl group, a tetrazinyl group, a thienyl group, a thiazolyl group, an isothiazolyl group, a thiadiazolyl group, furyl group, a pyrrolyl group, an imidazolyl group, a pyrazolyl group, oxazolyl group, an isoxazolyl group, a triazolyl group, an oxadiazolyl group, a thiadiazolyl group, tetrazolyl group and the like.

(26) The aryloxy group represents a combination of the above-mentioned aryl group and an oxygen atoms a bonding site. Specific examples of the aryloxy group may include a phenoxy group, a naphthyloxy group and the like.

(27) The heteroaryloxy group represents a combination of the above-mentioned heteroaryl group and an oxygen atoms a bonding site. Specific examples of the heteroaryloxy group may include a pyridyloxy group, a pyridazinyloxy group, a pyrimidinyloxy group, a pyrazinyloxy group, a triazinyloxy group, a tetrazinyloxy group, a thienyloxy group, a thiazolyloxy group, an isothiazolyloxy group, a thiadiazolyloxy group, a furyloxy group, a pyrrolyloxy group, an imidazolyloxy group, a pyrazolyloxy group, an oxazolyloxy group, an isoxazolyloxy group, a triazolyloxy group, an oxadiazolyloxy group, a thiadiazolyloxy group, a tetrazolyloxy group and the like.

(28) The aralkyloxy group represents a combination of an aralkyl group resulting from the substitution of the C1-C3 alkyl group with an aryl group such as a phenyl group, a naphthyl group and the like in place of hydrogen atom(s), and an oxygen atom as a bonding site. Specific examples of the aralkyloxy group may include a benzyloxy group, a phenethyloxy group, a phenylpropyloxy group, a naphthalenylmethoxy group, a naphthalenylethoxy group, a naphthalenylpropoxy group and the like.

(29) Specific examples of the 3 to 6 membered ring group containing 1 to 2 oxygen atoms may include a 1,2-epoxyethanyl group, an oxetanyl group, a oxolanyl group, an oxanyl group, a 1,3-dioxolanyl group, a 1,3-dioxanyl group, a 1,4-dioxanyl group and the like.

(30) The pyridone compound of the present invention include those compounds represented by Formula (1) below and salts thereof.

(31) ##STR00019##

(32) In the following, Formula (1) will be described.

(33) R1 in Formula (1) is a hydroxyl group, a cyano group, a C1-C6 alkyl group optionally substituted with substituent(s) A, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group optionally substituted with substituent(s) A, a C2-C6 alkenyl group optionally substituted with substituent(s) A, a C2-C6 haloalkenyl group, a C2-C6 alkynyl group optionally substituted with substituent(s) A, a C2-C6 haloalkynyl group, a C1-C6 alkoxy group optionally substituted with substituent(s) A, a C1-C6 haloalkoxy group, a C3-C8 cycloalkoxy group optionally substituted with substituent(s) A, a C2-C6 alkenyloxy group optionally substituted with substituent(s) A, a C2-C6 haloalkenyloxy group, a C3-C6 alkynyloxy group optionally substituted with substituent(s) A, a C3-C6 haloalkynyloxy group or RaRbN— (wherein Ra and Rb each independently represents a hydrogen atom, a C1-C6 alkyl group optionally substituted with substituent(s) B, a C1-C6 haloalkyl group or a C3-C8 cycloalkyl group or Ra and Rb together with the nitrogen atom to which they are bonded form an aziridinyl group, an azetidinyl group, a pyrrolidinyl group, a piperidinyl group, a homopiperidinyl group or an azocanyl group).

(34) Above all, R1 is preferably a C1-C6 alkyl group optionally substituted with substituent(s) A, a C1-C6 haloalkyl group, a C2-C6 alkenyl group optionally substituted with substituent(s) A, a C2-C6 haloalkenyl group, a C2-C6 alkynyl group optionally substituted with substituent(s) A, a C2-C6 haloalkynyl group or RaRbN— (wherein Ra and Rb are the same as defined hereinabove);

(35) R1 is particularly preferably a C1-C6 alkyl group optionally substituted with substituent(s) A, a C1-C6 haloalkyl group or RaRbN— (wherein Ra and Rb are the same as defined hereinabove);

(36) and R1 is further preferably a C1-C6 alkyl group, a C1-C6 haloalkyl group or RaRbN— (wherein Ra and Rb are the same as defined hereinabove).

(37) In R1 of Formula (1), a hydroxyl group and a cyano group are contained.

(38) The C1-C6 alkyl group of the “C1-C6 alkyl group optionally substituted with substituent(s) A” in R1 of Formula (1) is the same as defined hereinabove and preferably a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group or an isobutyl group, further preferably a methyl group, an ethyl group or a propyl group and particularly preferably a methyl group or an ethyl group. When it has the substituent(s) A, the C1-C6 alkyl group is optionally substituted with the substituent(s) A in place of hydrogen atom(s).

(39) The “C1-C6 haloalkyl group” in R1 of Formula (1) is the same as defined hereinabove, preferably a 2-fluoroethyl group, a 2,2-difluoroethyl group, a 2,2,2-trifluoroethyl group, a 3,3-difluoropropyl group or a 3,3,3-trifluoropropyl group, further preferably a 2-fluoroethyl group, a 2,2-difluoroethyl group or a 2,2,2-trifluoroethyl group and particularly preferably a 2,2-difluoroethyl group or a 2,2,2-trifluoroethyl group.

(40) The C3-C8 cycloalkyl group of the “C3-C8 cycloalkyl group optionally substituted with substituent(s) A” in R1 of Formula (1) is the same as defined hereinabove, preferably a cyclopropyl group, a cyclobutyl group, a cyclopentyl group or a cyclohexyl group and further preferably a cyclopropyl group or a cyclobutyl group. When it has the substituent(s) A, the C3-C8 cycloalkyl group is optionally substituted with the substituent(s) A in place of hydrogen atom(s).

(41) The C2-C6 alkenyl group of the “C2-C6 alkenyl group optionally substituted with substituent(s) A” in R1 of Formula (1) is the same as defined hereinabove, preferably a vinyl group, a 1-propenyl group or an allyl group and further preferably a vinyl group or an allyl group. When it has the substituent(s) A, the C2-C6 alkenyl group is optionally substituted with the substituent(s) A in place of hydrogen atom(s).

(42) The “C2-C6 haloalkenyl group” in R1 of Formula (1) is the same as defined hereinabove, preferably a 2-fluorovinyl group, a 2,2-difluorovinyl group, a 3-fluoroallyl group or a 3,3-difluoroallyl group and further preferably a 2-fluorovinyl group or a 2,2-difluorovinyl group.

(43) The C2-C6 alkynyl group of “C2-C6 alkynyl group optionally substituted with substituent(s) A” in R1 of Formula (1) is the same as defined hereinabove, preferably a propargyl group, a 2-butynyl group or a 3-butynyl group and further preferably a propargyl group. When it has the substituent(s) A, the C2-C6 alkynyl group is optionally substituted with the substituent(s) A in place of hydrogen atom(s).

(44) The “C2-C6 haloalkynyl group” in R1 of Formula (1) is the same as defined hereinabove, preferably 4,4-difluoro-2-butynyl group, a 4-chloro-4,4-difluoro-2-butynyl group, a 4-bromo-4,4-difluoro-2-butynyl group or a 4,4,4-trifluoro-2-butynyl group, further preferably a 4,4-difluoro-2-butynyl group or a 4,4,4-trifluoro-2-butynyl group.

(45) The C1-C6 alkoxy group of “C1-C6 alkoxy group optionally substituted with substituent(s) A” in R1 of Formula (1) is the same as defined hereinabove, preferably a methoxy group, an ethoxy group, a propyloxy group, an isopropyloxy group, a butoxy group or an isobutoxy group and further preferably a methoxy group or an ethoxy group.

(46) When it has the substituent(s) A, the C1-C6 alkoxy group is optionally substituted with the substituent(s) A in place of hydrogen atom(s).

(47) The “C1-C6 haloalkoxy group” in R1 of Formula (1) is the same as defined hereinabove, preferably a difluoromethoxy group, a trifluoromethoxy group, a 2,2-difluoroethoxy group, a 2,2,2-trifluoroethoxy group, a 3,3-difluoropropyloxy group or a 3,3,3-trifluoropropyloxy group and further preferably a difluoromethoxy group, a trifluoromethoxy group, a 2,2-difluoroethoxy group or a 2,2,2-trifluoroethoxy group.

(48) The C3-C8 cycloalkoxy group of the “C3-C8 cycloalkoxy group optionally substituted with substituent(s) A” in R1 of Formula (1) is the same as defined hereinabove, preferably a cyclopropyloxy group, a cyclobutoxy group, a cyclopentyloxy group or a cyclohexyloxy group and further preferably a cyclopropyloxy group or a cyclobutoxy group. When it has the substituent(s) A, the C3-C8 cycloalkoxy group is optionally substituted with the substituent(s) A in place of hydrogen atom(s).

(49) The C2-C6 alkenyloxy group of the “C2-C6 alkenyloxy group optionally substituted with substituent(s) A” in R1 of Formula (1) is the same as defined hereinabove, preferably a vinyloxy group, a 1-propenyloxy group or an allyloxy group and further preferably an allyloxy group. When it has the substituent(s) A, a hydrogen atom in the C2-C6 alkenyloxy group is optionally substituted with the substituent(s) A in place of hydrogen atom(s).

(50) The “C2-C6 haloalkenyloxy group” in R1 of Formula (1) is the same as defined hereinabove, preferably a 2-fluorovinyloxy group, a 2,2-difluorovinyloxy group, a 3-fluoroallyloxy group or a 3,3-difluoroallyloxy group and further preferably a 2-fluorovinyloxy group or a 2,2-difluorovinyloxy group.

(51) The C3-C6 alkynyloxy group of the “C3-C6 alkynyloxy group optionally substituted with substituent(s) A” in R1 of Formula (1) is the same as defined hereinabove, preferably a propargyloxy group, a 2-butynyloxy group or a 3-butynyloxy group and further preferably a propargyloxy group. When it has the substituent(s) A, a hydrogen atom of the C3-C6 alkynyloxy group is optionally substituted with the substituent(s) A in place of hydrogen atom(s).

(52) The “C3-C6 haloalkynyloxy group” in R1 of Formula (1) is the same as defined hereinabove, preferably a 4,4-difluoro-2-butynyloxy group, a 4-chloro-4,4-difluoro-2-butynyloxy group, a 4-bromo-4,4-difluoro-2-butynyloxy group or a 4,4,4-trifluoro-2-butynyloxy group and further preferably a 4,4-difluoro-2-butynyloxy group or a 4,4,4-trifluoro-2-butynyloxy group.

(53) Each term of the “RaRbN—” (wherein Ra and Rb each independently represents a hydrogen atom, a C1-C6 alkyl group optionally substituted with substituent(s) B, a C1-C6 haloalkyl group or a C3-C8 cycloalkyl group or Ra and Rb together with the nitrogen atom to which they are bonded form an aziridinyl group, an azetidinyl group, a pyrrolidinyl group, a piperidinyl group, a homopiperidinyl group or an azocanyl group.) in R1 of Formula (1) is the same as defined hereinabove. Incidentally, with regard to the “C1-C6 alkyl group optionally substituted with substituent(s) B”, when it has the substituent(s) B, the C1-C6 alkyl group is optionally substituted with the substituent(s) B in place of hydrogen atom(s). Ra and Rb are each preferably a hydrogen atom, a C1-C6 alkyl group optionally substituted with substituent(s) B, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group, a pyrrolidinyl group or a piperidinyl group and further preferably a hydrogen atom or a C1-C6 alkyl group optionally substituted with substituent(s) B. The “RaRbN—” is preferably an amino group, a methylamino group, an ethylamino group, a (methoxymethyl)amino group, a (2-methoxyethyl)amino group, a (cyanomethyl)amino group, a (2-cyanoethyl)amino group, a dimethylamino group, an ethylmethylamino group, a diethylamino group, a (methoxymethyl)methylamino group, a (2-methoxyethyl)methylamino group, a (cyanomethyl)methylamino group, a (2-cyanoethyl)methylamino group, a 2,2-difluoroethylamino group, a 2,2,2-trifluoroethylamino group, a cyclopropylamino group, a (cyclopropyl)methylamino group, a pyrrolidinyl group or a piperidinyl group, further preferably an amino group, a methylamino group, a dimethylamino group, an ethylmethylamino group or a diethylamino group and particularly preferably an amino group, a methylamino group or a dimethylamino group.

(54) R2 in Formula (1) represents a hydrogen atom, a nitro group, a halogen atom, a C1-C6 alkyl group optionally substituted with substituent(s) A, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group optionally substituted with substituent(s) A, a C2-C6 alkenyl group optionally substituted with substituent(s) A, a C2-C6 haloalkenyl group, a C2-C6 alkynyl group optionally substituted with substituent(s) A, a C2-C6 haloalkynyl group, a C1-C6 alkoxy group optionally substituted with substituent(s) A, a C1-C6 haloalkoxy group, a C3-C8 cycloalkoxy group optionally substituted with substituent(s) A, a C2-C6 alkenyloxy group optionally substituted with substituent(s) A, a C2-C6 haloalkenyloxy group, a C3-C6 alkynyloxy group optionally substituted with substituent(s) A, a C3-C6 haloalkynyloxy group, Rc-L- (wherein Rc represents a C1-C6 alkyl group or a C1-C6 haloalkyl group and L represents S, SO or SO.sub.2.) or Rx1C(═O)— (wherein Rx1 represents a hydrogen atom, a C1-C6 alkyl group optionally substituted with substituent(s) B, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C3-C8 cycloalkoxy group or RaRbN— (wherein Ra and Rb are the same as defined hereinabove)).

(55) Above all, R2 is preferably a hydrogen atom, a halogen atom, a C1-C6 alkyl group optionally substituted with substituent(s) A, a C1-C6 haloalkyl group, a C2-C6 alkynyl group optionally substituted with substituent(s) A, a C2-C6 haloalkynyl group, a C1-C6 alkoxy group optionally substituted with substituent(s) A, a C1-C6 haloalkoxy group, a C2-C6 alkenyloxy group optionally substituted with substituent(s) A, a C3-C6 alkynyloxy group optionally substituted with substituent(s) A, Rc-L- (wherein Rc and L are the same as defined hereinabove.) or Rx1C(═O)— (wherein Rx1 represents a hydrogen atom, a C1-C6 alkyl group optionally substituted with substituent(s) B, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C3-C8 cycloalkoxy group or RaRbN— (wherein Ra and Rb are the same as defined hereinabove));

(56) R2 is particularly preferably a hydrogen atom, a halogen atom, a C1-C6 alkyl group optionally substituted with substituent(s) A, a C1-C6 haloalkyl group, a C2-C6 alkynyl group optionally substituted with substituent(s) A, a C1-C6 alkoxy group optionally substituted with substituent(s) A or Rx1C(═O)— (wherein Rx1 represents a hydrogen atom, a C1-C6 alkyl group optionally substituted with substituent(s) B, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C3-C8 cycloalkoxy group or RaRbN— (wherein Ra and Rb are the same as defined hereinabove));

(57) and R2 is further preferably a hydrogen atom, a halogen atom, a C1-C6 alkyl group optionally substituted with substituent(s) A, a C1-C6 haloalkyl group, a C2-C6 alkynyl group optionally substituted with substituent(s) A or a C1-C6 alkoxy group optionally substituted with substituent(s) A.

(58) In R2 of Formula (1), a hydrogen atom and a nitro group are contained.

(59) The halogen atom in R2 of Formula (1) is the same as defined hereinabove, preferably a fluorine atom, a chlorine atom, a bromine atom or an iodine atom.

(60) The C1-C6 alkyl group of the “C1-C6 alkyl group optionally substituted with substituent(s) A” in R2 of Formula (1) is the same as defined hereinabove, preferably a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group or an isobutyl group, further preferably a methyl group or an ethyl group and particularly preferably a methyl group. When it has the substituent(s) A, the C1-C6 alkyl group is optionally substituted with the substituent(s) A in place of hydrogen atom(s).

(61) The “C1-C6 haloalkyl group” in R2 of Formula (1) is the same as defined hereinabove, preferably a difluoromethyl group, a trifluoromethyl group, a 2,2-difluoroethyl group, a 2,2,2-trifluoroethyl group, a 3,3-difluoropropyl group or a 3,3,3-trifluoropropyl group, further preferably a difluoromethyl group, a trifluoromethyl group, a 2,2-difluoroethyl group or a 2,2,2-trifluoroethyl group and particularly preferably a difluoromethyl group or a trifluoromethyl group.

(62) The C3-C8 cycloalkyl group of the “C3-C8 cycloalkyl group optionally substituted with substituent(s) A” in R2 of Formula (1) is the same as defined hereinabove, preferably a cyclopropyl group, a cyclobutyl group, a cyclopentyl group or a cyclohexyl group, and further preferably a cyclopropyl group or a cyclobutyl group. When it has the substituent(s) A, the C3-C8 cycloalkyl group is optionally substituted with the substituent(s) A in place of hydrogen atom(s).

(63) The C2-C6 alkenyl group of the “C2-C6 alkenyl group optionally substituted with substituent(s) A” in R2 of Formula. (1) is the same as defined hereinabove, preferably a vinyl group, a 1-propenyl group, an allyl group, a 1-butenyl group, a 2-butenyl group or a 3-butenyl group and further preferably a vinyl group, a 1-propenyl group or an allyl group. When it has the substituent(s) A, the C2-C6 alkenyl group is optionally substituted with the substituent(s) A in place of hydrogen atom(s).

(64) The “C2-C6 haloalkenyl group” in R2 of Formula (1) is the same as defined hereinabove, preferably a 2-fluorovinyl group, a 2,2-difluorovinyl group, a 2,2-dichlorovinyl group, a 3-fluoroallyl group, a 3,3-difluoroallyl group or a 3,3-dichloroallyl group and further preferably a 2-fluorovinyl group or a 2,2-difluorovinyl group.

(65) The C2-C6 alkynyl group of the “C2-C6 alkynyl group optionally substituted with substituent(s) A” in R2 of Formula (1) is the same as defined hereinabove, preferably an ethynyl group, a 1-propynyl group, a propargyl group, a 1-butynyl group, a 2-butynyl group or a 3-butynyl group, further preferably an ethynyl group, a 1-propynyl group or a propargyl group and particularly preferably an ethynyl group. When it has the substituent(s) A, the C2-C6 alkynyl group is optionally substituted with the substituent(s) A in place of hydrogen atom(s).

(66) The “C2-C6 haloalkynyl group” in R2 of Formula (1) is the same as defined hereinabove, preferably a 3,3-difluoro-1-propynyl group, a 3,3,3-trifluoro-1-propynyl group, a 4,4-difluoro-1-butynyl group, a 4,4-difluoro-2-butynyl group, a 4,4,4-trifluoro-1-butynyl group or a 4,4,4-trifluoro-2-butynyl group and further preferably a 3,3-difluoro-1-propynyl group or a 3,3,3-trifluoro-1-propynyl group.

(67) The C1-C6 alkoxy group of the “C1-C6 alkoxy group optionally substituted with substituent(s) A” in R2 of Formula (1) is the same as defined hereinabove, preferably a methoxy group, an ethoxy group, a propyloxy group, an isopropyloxy group, a butoxy group or an isobutoxy group, further preferably a methoxy group, an ethoxy group, a propyloxy group or an isopropyloxy group and particularly preferably a methoxy group. When it has the substituent(s) A, the C1-C6 alkoxy group is optionally substituted with the substituent(s) A in place of hydrogen atom(s).

(68) The “C1-C6 haloalkoxy group” in R2 of Formula (1) is the same as defined hereinabove, preferably a difluoromethoxy group, a trifluoromethoxy group, a 2,2-difluoroethoxy group, a 2,2,2-trifluoroethoxy group, a 3,3-difluoropropyloxy group or a 3,3,3-trifluoropropyloxy group and further preferably a difluoromethoxy group, a trifluoromethoxy group, a 2,2-difluoroethoxy group or a 2,2,2-trifluoroethoxy group.

(69) The C3-C8 cycloalkoxy group of the “C3-C8 cycloalkoxy group optionally substituted with substituent(s) A” in R2 of Formula (1) is the same as defined hereinabove, preferably a cyclopropyloxy group, a cyclobutoxy group, a cyclopentyloxy group or a cyclohexyloxy group and further preferably a cyclopropyloxy group or a cyclobutoxy group. When it has the substituent(s) A, the C3-C8 cycloalkoxy group is optionally substituted with the substituent(s) A in place of hydrogen atom(s).

(70) The C2-C6 alkenyloxy group of the “C2-C6 alkenyloxy group optionally substituted with substituent(s) A” in R2 of Formula (1) is the same as defined hereinabove, preferably a vinyloxy group, a 1-propenyloxy group, an allyloxy group, a 1-butenyloxy group, a 2-butenyloxy group or a 3-butenyloxy group and further preferably a vinyloxy group, a 1-propenyloxy group or an allyloxy group. When it has the substituent(s) A, the C2-C6 alkenyloxy group is optionally substituted with the substituent(s) A in place of hydrogen atom(s).

(71) The “C2-C6 haloalkenyloxy group” in R2 of Formula (1) is the same as defined hereinabove and is a 2-fluorovinyloxy group, a 2,2-difluorovinyloxy group, a 2,2-dichlorovinyloxy group, a 3-fluoroallyloxy group, a 3,3-difluoroallyloxy group or a 3,3-dichloroallyloxy group, further preferably a 2-fluorovinyloxy group or a 2,2-difluorovinyloxy group.

(72) The C3-C6 alkynyloxy group of the “C3-C6 alkynyloxy group optionally substituted with substituent(s) A” in R2 of Formula (1) is the same as defined hereinabove, preferably a propargyloxy group, a 2-butynyloxy group or a 3-butynyloxy group and further preferably a propargyloxy group. When it has the substituent(s) A, the C3-C6 alkynyloxy group is optionally substituted with the substituent(s) A in place of hydrogen atom(s).

(73) The “C3-C6 haloalkynyloxy group” in R2 of Formula (1) is the same as defined hereinabove, preferably a 4,4-difluoro-2-butynyloxy group, a 4-chloro-4,4-difluoro-2-butynyloxy group, a 4-bromo-4,4-difluoro-2-butynyloxy group or a 4,4,4-trifluoro-2-butynyloxy group and further preferably a 4,4-difluoro-2-butynyloxy group or a 4,4,4-trifluoro-2-butynyloxy group.

(74) Each term of the “Rc-L-” (wherein Rc represents a C1-C6 alkyl group or a C1-C6 haloalkyl group and L represents S, SO or SO.sub.2.) in R2 of Formula (1) is the same as defined hereinabove. The “Rc-L-” is preferably a methylthio group, a methanesulfinyl group, a methanesulfonyl group, a trifluoromethylthio group, a trifluoromethanesulfinyl group or a trifluoromethanesulfonyl group and further preferably a methylthio group, a methanesulfinyl group or a methanesulfonyl group.

(75) Each term of the “Rx1C(═O)—” (wherein Rx1 represents a hydrogen atom, a C1-C6 alkyl group optionally substituted with substituent(s) B, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C3-C8 cycloalkoxy group or RaRbN— (wherein Ra and Rb are the same as defined hereinabove)) in R2 of Formula (1) is the same as defined hereinabove. Incidentally, with regard to the “C1-C6 alkyl group optionally substituted with substituent(s) B”, when it has the substituent(s) B, the C1-C6 alkyl group is optionally substituted with the substituent(s) B in place of hydrogen atom(s). The Rx1 is preferably a hydrogen atom, a C1-C6 alkyl group optionally substituted with substituent(s) B, a C1-C6 haloalkyl group or C1-C6 alkoxy group, further preferably a hydrogen atom, a C1-C6 alkyl group optionally substituted with substituent(s) B or C1-C6 alkoxy group and particularly preferably a hydrogen atom. The “Rx1C(═O)—” is a formyl group, an acetyl group, a methoxyacetyl group, a cyanoacetyl group, a propionyl group, a difluoroacetyl group, a trifluoroacetyl group, a cyclopropancarbonyl group, a methoxycarbonyl group, an ethoxycarbonyl group, a 2,2-difluoroethoxycarbonyl group, a 2,2,2-trifluoroethoxycarbonyl group, a 3,3,3-trifluoropropyloxycarbonyl group, a cyclopropyloxycarbonyl group, an aminocarbonyl group, a methylaminocarbonyl group, an ethylaminocarbonyl group, a (methoxymethyl)aminocarbonyl group, a (2-methoxyethyl)aminocarbonyl group, a (cyanomethyl)aminocarbonyl group, a (2-cyanoethyl)aminocarbonyl group, a dimethylaminocarbonyl group, an ethylmethylaminocarbonyl group, a diethylaminocarbonyl group, a (methoxymethyl)methylaminocarbonyl group, a (2-methoxyethyl)-methylaminocarbonyl group, a (cyanomethyl)methylaminocarbonyl group, a (2-cyanoethyl)methylaminocarbonyl group, a 2,2-difluoroethylaminocarbonyl group, a 2,2,2-trifluoroethylaminocarbonyl group, a cyclopropylaminocarbonyl group, a (cyclopropyl)methylaminocarbonyl group, a pyrrolidinylcarbonyl group, a piperidinylcarbonyl group and the like. The “Rx1C(═O)—” is preferably a formyl group, an acetyl group, a methoxyacetyl group, a cyanoacetyl group, a propionyl group, a difluoroacetyl group, a trifluoroacetyl group, a methoxycarbonyl group or an ethoxycarbonyl group, further preferably a formyl group, an acetyl group, a methoxyacetyl group, a cyanoacetyl group, a methoxycarbonyl group or an ethoxycarbonyl group and particularly preferably a formyl group.

(76) In Formula (1), Het represents a 5 to 6-membered heterocyclic group or the 8 to 10-membered heterocyclic group.

(77) The 5 to 6-membered heterocyclic group or the 8 to 10-membered heterocyclic group is optionally substituted with 0 to 6 substituents R3 (with the proviso that when two or more substituents R3 are present, each R3 represents an independent substituent).

(78) Specific examples of the 5 to 6-membered heterocyclic group may include a pyridyl group, a pyridazinyl group, a pyrimidinyl group, a pyrazinyl group, a triazinyl group, a tetrazinyl group, a thienyl group, a thiazolyl group, an isothiazolyl group, a thiadiazolyl group, a thiatriazolyl group, a pyrrolyl group, a pyrazolyl group, an imidazolyl group, a triazolyl group, a tetrazolyl group, a pentazolyl group, a furyl group, an oxazolyl group or a 3 to 6-membered ring group containing 1 to 2 oxygen atoms and the like.

(79) Specific examples of the 8 to 10-membered heterocyclic group may include an indolyl group, an isoindolyl group, an indazolyl group, a benzimidazolyl group, a benzotriazolyl group, a benzofuryl group, an isobenzofuryl group, a benzoxazolyl group, a benzothienyl group, benzothiazolyl group, a benzisothiazolyl group, a benzothiadiazolyl group, an indolidinyl group, an imidazopyridyl group, a pyrazolopyridyl group, a triazolopyridyl group, a pyrrolopyrimidinyl group, an imidazopyrimidinyl group, a pyrazolopyrimidinyl group, a triazolopyrimidinyl group, a pyrrolopyrazinyl group, an imidazopyrazinyl group, a pyrazolopyrazinyl group, a triazolopyrazinyl group, a quinolyl group, an isoquinolyl group, a cinnolyl group, a phthalazinyl group, a quinoxalynyl group, a quinazolynyl group or a naphthylidinyl group and the like.

(80) Above all, Het is preferably a 5 to 6-membered heterocyclic group, and is specifically preferably a pyridyl group, a pyridazinyl group, a pyrimidinyl group, a pyrazinyl group, a triazinyl group, a tetrazinyl group, a thienyl group, a thiazolyl group, an isothiazolyl group, a thiadiazolyl group, a thiatriazolyl group, a pyrrolyl group, a pyrazolyl group, an imidazolyl group, a triazolyl group, a tetrazolyl group, a pentazolyl group, a furyl group, an oxazolyl group or a 3 to 6-membered ring group containing 1 to 2 oxygen atoms; and

(81) Het is particularly preferably a pyridyl group, a thienyl group, a pyrrolyl group, a pyrazolyl group, an imidazolyl group, a triazolyl group, a tetrazolyl group, an oxazolyl group or a 3 to 6-membered ring, group containing 1 to 2 oxygen atoms.

(82) Het is further preferably a pyridyl group, a thienyl group, a pyrrolyl group, a pyrazolyl group, an imidazolyl group, a triazolyl group, an oxazolyl group or a 3 to 6-membered ring group containing 1 to 2 oxygen atoms.

(83) The pyridyl group, the pyridazinyl group, the pyrimidinyl group, the pyrazinyl group, the triazinyl group or the tetrazinyl group is optionally substituted with 0 to 4 substituents R3. (with the proviso that when two or more substituents R3 are present, each R3 represents an independent substituent.)

(84) The thienyl group, the thiazolyl group, the isothiazolyl group, the thiadiazolyl group or the thiatriazolyl group is optionally substituted with 0 to 3 substituents R3. (with the proviso that when two or more substituents R3 are present, each R3 represents an independent substituent.)

(85) The pyrrolyl group, the pyrazolyl group, the imidazolyl group, the triazolyl group, the tetrazolyl group or the pentazolyl group is optionally substituted with 0 to 4 substituents R3. (with the proviso that when two or more substituents R3 are present, each R3 represents an independent substituent.)

(86) The furyl group or the oxazolyl group is optionally substituted with 0 to 3 substituents R3. (with the proviso that when two or more substituents R3 are present, each R3 represents an independent substituent.)

(87) The indolyl group, the isoindolyl group, the indazolyl group, the benzimidazolyl group or the benzotriazolyl group is optionally substituted with 0 to 6 substituents R3. (with the proviso that when two or more substituents R3 are present, each R3 represents an independent substituent.)

(88) The benzofuryl group, the isobenzofuryl group or the benzoxazolyl group is optionally substituted with 0 to 5 substituents R3. (with the proviso that when two or more substituents R3 are present, each R3 represents an independent substituent.)

(89) The benzothienyl group, the benzothiazolyl group, the benzisothiazolyl group or the benzothiadiazolyl group is optionally substituted with 0 to 5 substituents R3. (with the proviso that when two or more substituents R3 are present, each R3 represents an independent substituent.)

(90) The indolidinyl group, the imidazopyridyl group, the pyrazolopyridyl group or the triazolopyridyl group is optionally substituted with 0 to 6 substituents R3. (with the proviso that when two or more substituents R3 are present, each R3 represents an independent substituent.)

(91) The pyrrolopyrimidinyl group, the imidazopyrimidinyl group, the pyrazolopyrimidinyl group, the triazolopyrimidinyl group, the pyrrolopyrazinyl group, the imidazopyrazinyl group, the pyrazolopyrazinyl group or the triazolopyrazinyl group is optionally substituted with 0 to 5 substituents R3. (with the proviso that when two or more substituents R3 are present, each R3 represents an independent substituent.)

(92) The quinolyl group, the isoquinolyl group, the cinnolyl group, the phthalazinyl group, the quinoxalynyl group, the quinazolynyl group or the naphthylidinyl group is optionally substituted with 0 to 6 substituents R3. (with the proviso that when two or more substituents R3 are present, each R3 represents an independent substituent.)

(93) R3 represents a hydroxyl group, a cyano group, a nitro group, a halogen atom, a C1-C6 alkyl group optionally substituted with substituent(s) C, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group optionally substituted with substituent(s) C, a C2-C6 alkenyl group optionally substituted with substituent(s) C, a C2-C6 haloalkenyl group, a C2-C6 alkynyl group optionally substituted with substituent(s) C, a C2-C6 haloalkynyl group, a CL-C6 alkoxy group optionally substituted with substituent(s) C, a C1-C6 haloalkoxy group, a C3-C8 cycloalkoxy group optionally substituted with substituent(s) C, a C2-C6 alkenyloxy group optionally substituted with substituent(s) C, a C2-C6 haloalkenyloxy group, a C3-C6 alkynyloxy group optionally substituted with substituent(s) C, a C3-C6 haloalkynyloxy group, an aryl group optionally substituted with substituent(s) D, a heteroaryl group optionally substituted with substituent(s) D, an aryloxy group optionally substituted with substituent(s) D, a heteroaryloxy group optionally substituted with substituent(s) D, an aralkyloxy group optionally substituted with substituent(s) D, RaRbN— (wherein Ra and Rb are the same as defined hereinabove), Rc-L- (wherein Rc and L are the same as defined hereinabove),

(94) Rx1C(═O)— (wherein Rx1 is the same as defined hereinabove), Rx1C(═O)O— (wherein Rx1 is the same as defined hereinabove), Rx2C(═O)N(Rx3)- (wherein Rx2 represents a hydrogen atom, a C1-C6 alkyl group optionally substituted with substituent(s) B, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C3-C8 cycloalkoxy group or RaRbN— (wherein Ra and Rb are the same as defined hereinabove), Rx3 represents a hydrogen atom, a C1-C6 alkyl group optionally substituted with substituent(s) B, a C1-C6 haloalkyl group or a C3-C8 cycloalkyl group), Rx4Rx5C═N—O— (wherein Rx4 and Rx5 each independently represent a hydrogen atom, a C1-C6 alkyl group optionally substituted with substituent(s) B, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C3-C8 cycloalkoxy group or RaRbN— (wherein Ra and Rb are the same as defined hereinabove)) or a 3 to 6-membered ring group containing 1 to 2 oxygen atoms.

(95) Above all, R3 is preferably a cyano group, a nitro group, a halogen atom, a C1-C6 alkyl group optionally substituted with substituent(s) C, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group optionally substituted with substituent(s) C, a C2-C6 alkenyl group optionally substituted with substituent(s) C, a C2-C6 alkynyl group optionally substituted with substituent(s) C, a C1-C6 alkoxy group optionally substituted with substituent(s) C, a C1-C6 haloalkoxy group, a C3-C8 cycloalkoxy group optionally substituted with substituent(s) C, a C2-C6 alkenyloxy group optionally substituted with substituent(s) C, a C3-C6 alkynyloxy group optionally substituted with substituent(s) C, RaRbN— (wherein Ra and Rb are the same as defined hereinabove), Rc-L- (wherein Rc and L are the same as defined hereinabove), Rx1C(═O)— (wherein Rx1 is the same as defined hereinabove), Rx1C(═O)O— (wherein Rx1 is the same as defined hereinabove.) or Rx2C(═O)N(Rx3)- (wherein Rx2 and Rx3 are the same as defined hereinabove); R3 is particularly preferably a cyano group, a nitro group, a halogen atom, a C1-C6 alkyl group optionally substituted with substituent(s) C, a C1-C6 haloalkyl group, a C1-C6 alkoxy group optionally substituted with substituent(s) C, RaRbN— (wherein Ra and Rb are the same as defined hereinabove), Rx1C(═O)— (wherein Rx1 is the same as defined hereinabove.) or Rx2C(═O)N(Rx3)- (wherein Rx2 and Rx3 are the same as defined hereinabove);

(96) and R3 is further preferably a cyano group, a nitro group, a halogen atom, a C1-C6 alkyl group optionally substituted with substituent(s) C, a C1-C6 haloalkyl group, a C1-C6 alkoxy group optionally substituted with substituent(s) C, RaRbN— (wherein Ra and Rb are the same as defined hereinabove), or Rx1C(═O)— (wherein Rx1 is the same as defined hereinabove).

(97) In R3 of Formula (1), a hydroxyl group, a cyano group and a nitro group are contained.

(98) The halogen atom in R3 of Formula (1) is the same as defined hereinabove, preferably a fluorine atom, a chlorine atom, a bromine atom or an iodine atom.

(99) The C1-C6 alkyl group of the “C1-C6 alkyl group optionally substituted with substituent(s) C” in R3 of Formula (I) is the same as defined hereinabove, preferably a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group or an isobutyl group, further preferably a methyl group, an ethyl group or a propyl group and particularly preferably a methyl group. When it has the substituent(s) C, the C1-C6 alkyl group is optionally substituted with the substituent(s) C in place of hydrogen atom(s).

(100) The “C1-C6 haloalkyl group” in R3 of Formula (1) is the same as defined hereinabove, preferably a monofluoromethyl group, a monochloromethyl group, a monobromomethyl group, a difluoromethyl group, a trifluoromethyl group, a 2,2-difluoroethyl group, a 2,2,2-trifluoroethyl group, a 3,3-difluoropropyl group or a 3,3,3-trifluoropropyl group, further preferably a monobromomethyl group, a difluoromethyl group, a trifluoromethyl group, a 2,2-difluoroethyl group or a 2,2,2-trifluoroethyl group and particularly preferably monobromomethyl group, a difluoromethyl group or a trifluoromethyl group.

(101) The C3-C8 cycloalkyl group of the “C3-C8 cycloalkyl group optionally substituted with substituent(s) C” in R3 of Formula (1) is the same as defined hereinabove, preferably a cyclopropyl group, a cyclobutyl group, a cyclopentyl group or a cyclohexyl group, further preferably a cyclopropyl group or a cyclobutyl group. When it has the substituent(s) C, the C3-C8 cycloalkyl group is optionally substituted with the substituent(s) C in place of hydrogen atom(s).

(102) The C2-C6 alkenyl group of the “C2-C6 alkenyl group optionally substituted with substituent(s) C” in R3 of Formula (1) is the same as defined hereinabove, preferably a vinyl group, a 1-propenyl group, an allyl group, a 1-butenyl group, a 2-butenyl group or a 3-butenyl group and further preferably a vinyl group, a 1-propenyl group or an allyl group. When it has the substituent(s) C, the C2-C6 alkenyl group is optionally substituted with the substituent(s) C in place of hydrogen atom(s).

(103) The “C2-C6 haloalkenyl group” in R3 of Formula (1) is the same as defined hereinabove, preferably a 2-fluorovinyl group, a 2,2-difluorovinyl group, a 2,2-dichlorovinyl group, a 3-fluoroallyl group, a 3,3-difluoroallyl group or a 3,3-dichloroallyl group and further preferably a 2-fluorovinyl group or a 2,2-difluorovinyl group.

(104) The C2-C6 alkynyl group of the “C2-C6 alkynyl group optionally substituted with substituent(s) C” in R3 of Formula (1) is the same as defined hereinabove, preferably an ethynyl group, a 1-propynyl group, a propargyl group, a 1-butynyl group, a 2-butynyl group or a 3-butynyl group and further preferably an ethynyl group, a 1-propynyl group or a propargyl group. When it has the substituent(s) C, the C2-C6 alkynyl group is optionally substituted with the substituent(s) C in place of hydrogen atom(s).

(105) The “C2-C6 haloalkynyl group” in R3 of Formula (1) is the same as defined hereinabove, preferably a 3,3-difluoro-1-propynyl group, a 3,3,3-trifluoro-1-propynyl group, a 4,4-difluoro-1-butynyl group, a 4,4-difluoro-2-butynyl group, a 4,4,4-trifluoro-1-butynyl group or a 4,4,4-trifluoro-2-butynyl group and further preferably a 3,3-difluoro-1-propynyl group or a 3,3,3-trifluoro-1-propynyl group.

(106) The C1-C6 alkoxy group of the “C1-C6 alkoxyl group optionally substituted with substituent(s) C” in R3 of Formula (1) is the same as defined hereinabove, preferably a methoxy group, an ethoxy group, a propyloxy group, an isopropyloxy group, a butoxy group or an isobutoxy group, further preferably a methoxy group, an ethoxy group, a propyloxy group or an isopropyloxy group and particularly preferably a methoxy group. When it has the substituent(s) C, the C1-C6 alkoxy group is optionally substituted with the substituent(s) C in place of hydrogen atom(s).

(107) The “C1-C6 haloalkoxy group” in R3 of Formula (1) is the same as defined hereinabove, preferably a difluoromethoxy group, a trifluoromethoxy group, a 2,2-difluoroethoxy group, a 2,2,2-trifluoroethoxy group, a 3,3-difluoropropyloxy group or a 3,3,3-trifluoropropyloxy group and further preferably a difluoromethoxy group, a trifluoromethoxy group, a 2,2-difluoroethoxy group or a 2,2,2-trifluoroethoxy group.

(108) The C3-C8 cycloalkoxy group of the “C3-C8 cycloalkoxy group optionally substituted with substituent(s) C” in R3 of Formula (1) is the same as defined hereinabove, preferably a cyclopropyloxy group, a cyclobutoxy group, a cyclopentyloxy group or a cyclohexyloxy group and further preferably a cyclopropyloxy group or a cyclobutoxy group. When it has the substituent(s) C, the C3-C8 cycloalkoxy group is optionally substituted with the substituent(s) C in place of hydrogen atom(s).

(109) The C2-C6 alkenyloxy group of the “C2-C6 alkenyloxy group optionally substituted with substituent(s) C” in R3 of Formula (1) is the same as defined hereinabove, preferably a vinyloxy group, a 1-propenyloxy group, an allyloxy group, a 1-butenyloxy group, a 2-butenyloxy group or a 3-butenyloxy group and further preferably a vinyloxy group, a 1-propenyloxy group or an allyloxy group. When it has the substituent(s) C, the C2-C6 alkenyloxy group is optionally substituted with the substituent(s) C in place of hydrogen atom(s).

(110) The “C2-C6 haloalkenyloxy group” in R3 of Formula (1) is the same as defined hereinabove, preferably a 2-fluorovinyloxy group, a 2,2-difluorovinyloxy group, a 2,2-dichlorovinyloxy group, a 3-fluoroallyloxy group, a 3,3-difluoroallyloxy group or a 3,3-dichloroallyloxy group and further preferably a 2-fluorovinyloxy group or a 2,2-difluorovinyloxy group.

(111) The C3-C6 alkynyloxy group of the “C3-C6 alkynyloxy group optionally substituted with substituent(s) C” in R3 of Formula (1) is the same as defined hereinabove, preferably a propargyloxy group, a 2-butynyloxy group or a 3-butynyloxy group and further preferably a propargyloxy group. When it has the substituent(s) C, the C3-C6 alkynyloxy group is optionally substituted with the substituent(s) C in place of hydrogen atom(s).

(112) The “C3-C6 haloalkynyloxy group” in R3 of Formula (1) is the same as defined hereinabove, preferably a 4,4-difluoro-2-butynyloxy group, a 4-chloro-4,4-difluoro-2-butynyloxy group, a 4-bromo-4,4-difluoro-2-butynyloxy group or a 4,4,4-trifluoro-2-butynyloxy group and further preferably a 4,4-difluoro-2-butynyloxy group or a 4,4,4-trifluoro-2-butynyloxy group.

(113) The aryl group of the “aryl group optionally substituted with substituent(s) D” in R3 of Formula (1) is the same as defined hereinabove, preferably phenyl group. When it has the substituent(s) D, the aryl group is optionally substituted with the substituent(s) D in place of hydrogen(s).

(114) The heteroaryl group of the “heteroaryl group optionally substituted with substituent(s) D” in R3 of Formula (1) is the same as defined hereinabove, preferably a pyridyl group, a pyrazinyl group, a thienyl group, a thiazolyl group, an isothiazolyl group, furyl group, an imidazolyl group, a pyrazolyl group, oxazolyl group, an isoxazolyl group, a triazolyl group, an oxadiazolyl group or a tetrazolyl group and further preferably a pyridyl group, an imidazolyl group, a pyrazolyl group, triazolyl group or a tetrazolyl group. When it has the substituent(s) D, the heteroaryl group is optionally substituted with the substituent(s) D in place of hydrogen(s).

(115) The aryloxy group of the “aryloxy group optionally substituted with substituent(s) D” in R3 of Formula (1) is the same as defined hereinabove, preferably a phenoxy group or a naphthyloxy group and further preferably a phenoxy group. When it has the substituent(s) D, the aryloxy group is optionally substituted with the substituent(s) D in place of hydrogen atom(s).

(116) The heteroaryloxy group of the “heteroaryloxy group optionally substituted with substituent(s) D” in R3 of Formula (1) is the same as defined hereinabove, preferably a pyridyloxy group, a pyridazinyloxy group, a pyrimidinyloxy group, a pyrazinyloxy group, a pyrazolyloxy group, a triazinyloxy group, a tetrazinyloxy group, a thienyloxy group, a thiazolyloxy group, an isothiazolyloxy group or a thiadiazolyloxy group and further preferably a pyridyloxy group, a pyridazinyloxy group, a pyrimidinyloxy group, a pyrazinyloxy group or a pyrazolyloxy group. When it has the substituent(s) D, the heteroaryloxy group is optionally substituted with the substituent(s) D in place of hydrogen atom(s).

(117) The aralkyloxy group of the “aralkyloxy group optionally substituted with substituent(s) D” in R3 of Formula (1) is the same as defined hereinabove, preferably a benzyloxy group, a phenethyloxy group or a phenylpropyloxy group and further preferably a benzyloxy group or a phenethyloxy group. When it has the substituent(s) D, the aralkyloxy group is optionally substituted with the substituent(s) D in place of hydrogen atom(s).

(118) Ra and Rb of “RaRbN—” in R3 of Formula (1) are the same as defined hereinabove. Ra and Rb are each preferably a hydrogen atom, a C1-C6 alkyl group optionally substituted with substituent(s) B, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group, pyrrolidinyl group or a piperidinyl group and further preferably a hydrogen atom or a C1-C6 alkyl group optionally substituted with substituent(s) B. The “RaRbN—” is preferably an amino group, a methylamino group, an ethylamino group, a (methoxymethyl)amino group, a (2-methoxyethyl)amino group, a (cyanomethyl)amino group, a (2-cyanoethyl)amino group, a dimethylamino group, an ethylmethylamino group, a diethylamino group, a (methoxymethyl)methylamino group, a (2-methoxyethyl)methylamino group, a (cyanomethyl)methylamino group, a (2-cyanoethyl)methylamino group, a 2,2-difluoroethylamino group, a 2,2,2-trifluoroethylamino group, a cyclopropylamino group, a (cyclopropyl)methylamino group, a pyrrolidinyl group or a piperidinyl group, further preferably an amino group, a methylamino group, a dimethylamino group, an ethylmethylamino group or a diethylamino group and particularly preferably an amino group, a methylamino group or a dimethylamino group.

(119) Rc and L of “Rc-L-” in R3 of Formula (1) are the same as defined hereinabove. The “Rc-L-” is preferably a methylthio group, a methanesulfinyl group, a methanesulfonyl group, a trifluoromethylthio group, a trifluoromethanesulfinyl group or a trifluoromethanesulfonyl group and further preferably a methylthio group, a methanesulfinyl group or a methanesulfonyl group.

(120) Rx1 of “Rx1C(═O)—” in R3 of Formula (1) is the same as defined hereinabove. Rx1 is preferably a hydrogen atom, a C1-C6 alkyl group optionally substituted with substituent(s) B, a C1-C6 haloalkyl group or C1-C6 alkoxy group, further preferably a hydrogen atom, a C1-C6 alkyl group optionally substituted with substituent(s) B or C1-C6 alkoxy group and particularly preferably a hydrogen atom. The “Rx1C(═O)—” is preferably a formyl group, an acetyl group, a methoxyacetyl group, a cyanoacetyl group, a propionyl group, a difluoroacetyl group, a trifluoroacetyl group, a cyclopropancarbonyl group, a methoxycarbonyl group, an ethoxycarbonyl group, a 2,2-difluoroethoxycarbonyl group, a 2,2,2-trifluoroethoxycarbonyl group, a 3,3,3-trifluoropropyloxycarbonyl group, a cyclopropyloxycarbonyl group, an aminocarbonyl group, a methylaminocarbonyl group, an ethylaminocarbonyl group, a (methoxymethyl)aminocarbonyl group, a (2-methoxyethyl)aminocarbonyl group, a (cyanomethyl)aminocarbonyl group, a (2-cyanoethyl)aminocarbonyl group, a dimethylaminocarbonyl group, an ethylmethylaminocarbonyl group, a diethylaminocarbonyl group, a (methoxymethyl)methylaminocarbonyl group, a (2-methoxyethyl)methylaminocarbonyl group, a (cyanomethyl)methylaminocarbonyl group, a (2-cyanoethyl)methylaminocarbonyl group, a 2,2-difluoroethylaminocarbonyl group, a 2,2,2-trifluoroethylaminocarbonyl group, a cyclopropylaminocarbonyl group, a (cyclopropyl)methylaminocarbonyl group, a pyrrolidinylcarbonyl group or a piperidinylcarbonyl group, further preferably a formyl group, an acetyl group, a methoxyacetyl group, a cyanoacetyl group, a propionyl group, a difluoroacetyl group, a trifluoroacetyl group, a methoxycarbonyl group, an ethoxycarbonyl group and particularly preferably a formyl group or an ethoxycarbonyl group.

(121) Rx1 of “Rx1C(═O)O—” in R3 of Formula (1) is the same as defined hereinabove. The “Rx1C(═O)O—” is preferably a formyloxy group, an acetyloxy group, a methoxyacetyloxy group, a cyanoacetyloxy group, a propionyloxy group, a difluoroacetyloxy group, a trifluoroacetyloxy group, a cyclopropancarbonyloxy group, a methoxycarbonyloxy group, an ethoxycarbonyloxy group, a 2,2-difluoroethoxycarbonyloxy group, a 2,2,2-trifluoroethoxycarbonyloxy group, a 3,3,3-trifluoropropyloxycarbonyloxy group, a cyclopropyloxycarbonyloxy group, an aminocarbonyloxy group, a methylaminocarbonyloxy group, an ethylaminocarbonyloxy group, a (methoxymethyl)aminocarbonyloxy group, a (2-methoxyethyl)aminocarbonyloxy group, a (cyanomethyl)aminocarbonyloxy group, a (2-cyanoethyl)aminocarbonyloxy group, a dimethylaminocarbonyloxy group, an ethylmethylaminocarbonyloxy group, a diethylaminocarbonyloxy group, a (methoxymethyl)methylaminocarbonyloxy group, a (2-methoxyethyl)methylaminocarbonyloxy group, a (cyanomethyl)methylamino-carbonyloxy group, a (2-cyanoethyl)methylaminocarbonyloxy group, a 2,2-difluoroethylaminocarbonyloxy group, a 2,2,2-trifluoroethylaminocarbonyloxy group, a cyclopropylaminocarbonyloxy group, a (cyclopropyl)methylaminocarbonyloxy group, a pyrrolidinylcarbonyloxy group or a piperidinylcarbonyloxy group and further preferably a formyloxy group, an acetyloxy group or a trifluoroacetyloxy group.

(122) Each term of “Rx2C(═O)N(Rx3)-” (wherein Rx2 represents a hydrogen atom, a C1-C6 alkyl group optionally substituted with substituent(s) B, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C3-C8 cycloalkoxy group or RaRbN— (wherein Ra and Rb are the same as defined hereinabove), Rx3 represents a hydrogen atom, a C1-C6 alkyl group optionally substituted with substituent(s) B, a C1-C6 haloalkyl group or a C3-C8 cycloalkyl group.) in R3 of Formula (1) is the same as defined hereinabove. Incidentally, with regard to the “C1-C6 alkyl group optionally substituted with substituent(s) B”, when it has the substituent(s) B, the C1-C6 alkyl group is optionally substituted with the substituent(s) B in place of hydrogen atom(s). The Rx2 is preferably a hydrogen atom, a C1-C6 alkyl group optionally substituted with substituent(s) B, a C1-C6 haloalkyl group, a C1-C6 alkoxy group or RaRbN— (wherein Ra and Rb are the same as defined hereinabove.) and further preferably a C1-C6 alkyl group optionally substituted with substituent(s) B. The Rx3 is preferably a hydrogen atom, a C1-C6 alkyl group optionally substituted with substituent(s) B or C1-C6 haloalkyl group and further preferably a hydrogen atom. Specific examples of the Rx2 is preferably a hydrogen atom, a methyl group, a methoxymethyl group, a cyanomethyl group, an ethyl group, a difluoromethyl group, a trifluoromethyl group, a cyclopropyl group, a methoxy group, an ethoxy group, a 2,2-difluoroethoxy, a 2,2,2-trifluoroethoxy group, a cyclopropyloxy group, an amino group, a methylamino group, an ethylamino group, a (methoxymethyl)amino group, a (2-methoxyethyl)amino group, a (cyanomethyl)amino group, a (2-cyanoethyl)amino group, a dimethylamino group, an ethylmethylamino group, a diethylamino group, a (methoxymethyl)methylamino group, a (2-methoxyethyl)methylamino group, a (cyanomethyl)methylamino group, a (2-cyanoethyl)methylamino group, a 2,2-difluoroethylamino group, a 2,2,2-trifluoroethylamino group, a cyclopropylamino group, a (cyclopropyl)methylamino group, a pyrrolidinyl group or a piperidinyl group, further preferably a hydrogen atom, a methyl group, a methoxymethyl group, a cyanomethyl group, a difluoromethyl group, a trifluoromethyl group, a methoxy group, an ethoxy group, an amino group, a dimethylamino group, an ethylmethylamino group or a diethylamino group and particularly preferably a methyl group. Also, specific examples of the Rx3 is preferably a hydrogen atom, a methyl group, a methoxymethyl group, an ethoxymethyl group, a cyanomethyl group, an ethyl group, a 2-methoxyethyl group, a 2-ethoxyethyl group, a 2-cyanoethyl group, a propyl group, a 2,2-difluoroethyl group, a 2,2,2-trifluoroethyl group or a cyclopropyl group, further preferably a hydrogen atom, a methyl group, a methoxymethyl group, a cyanomethyl group, an ethyl group, a 2-methoxyethyl group, a 2,2-difluoroethyl group or a 2,2,2-trifluoroethyl group and particularly preferably a hydrogen atom. Further, the “Rx2C(═O)N(Rx3)-” is preferably an acetylamide group, a 2,2,2-trifluoroacetylamide group, a methylcarbamate group or an ethylcarbamate group and further preferably an acetylamide group.

(123) Each term of the “Rx4Rx5C═N—O—” (wherein Rx4 and Rx5 each independently represent a hydrogen atom, a C1-C6 alkyl group optionally substituted with substituent(s) B, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C3-C8 cycloalkoxy group or RaRbN— (wherein Ra and Rb are the same as defined hereinabove)) in R3 of Formula (1) is the same as defined hereinabove. Incidentally, with regard to the “C1-C6 alkyl group optionally substituted with substituent(s) B”, when it has the substituent(s) B, the C1-C6 alkyl group is optionally substituted with the substituent(s) B in place of hydrogen atom(s).

(124) Rx4 and Rx5 are each preferably a methyl group, an ethyl group, a propyl group, an isopropyl group, a trifluoromethyl group, a 2,2,2-trifluoroethyl group, a cyclopropyl group, a cyclopentyl group, a cyclohexyl group, a methoxy group, an ethoxy group, isopropyloxy group, a difluoromethoxy group, a trifluoromethoxy group, a 2,2-difluoroethoxy group, a 2,2,2-trifluoroethoxy group, a cyclopropyloxy group, a cyclobutyloxy group, a cyclopentyloxy group, an amino group, a methylamino group, an ethylamino group, a (methoxymethyl)amino group, a (2-methoxyethyl)amino group, a (cyanomethyl)amino group, a (2-cyanoethyl)amino group, a dimethylamino group, an ethylmethylamino group, a diethylamino group, a (methoxymethyl)methylamino group, a (2-methoxyethyl)methylamino group, a (cyanomethyl)methylamino group, a (2-cyanoethyl)methylamino group, a 2,2-difluoroethylamino group, a 2,2,2-trifluoroethylamino group, a cyclopropylamino group, a (cyclopropyl)methylamino group, a pyrrolidinyl group or a piperidinyl group and further preferably a methyl group, an ethyl group, a trifluoromethyl group, a 2,2,2-trifluoroethyl group, a methoxy group, an ethoxy group, a 2,2,2-trifluoroethoxy group, a dimethylamino group, an ethylmethylamino group or a diethylamino group.

(125) The “3 to 6 membered ring group containing 1 to 2 oxygen atoms” in R3 of Formula (1) is the same as defined hereinabove, preferably an oxolanyl group, an oxanyl group, a 1,3-dioxolanyl group or a 1,3-dioxanyl group and further preferably a 1,3-dioxolanyl group or a 1,3-dioxanyl group.

(126) In the following, Het in Formula (1) will be described in detail.

(127) A) When Het is a pyridyl group, a pyridazinyl group, a pyrimidinyl group, a pyrazinyl group, a triazinyl group or tetrazinyl group, Het represents a partial structure represented by Formula (a)

(128) ##STR00020##
(wherein R3 is the same as defined hereinabove and “na” represents an integer of 0 to 4).

(129) G1, G2, G3, G4 and G5 in Formula (a) are each independent and represent a carbon atom or a nitrogen atom. With the proviso that at least one among G1, G2, G3, G4 and G5 is a nitrogen atom. Preferred G1, G2, G3, G4 and G5 are that any one of G1, G2, G3, G4 and G5 is a nitrogen atom. That is, it is a pyridyl group.

(130) “na” in Formula (a) represents an integer of 0 to 4.

(131) When “na” in Formula (a) is 2 or more, the two or more substituents R3 are independent of one another and may be selected appropriately to be the same as or different from one another.

(132) Specific examples of the partial structures of Formula (a) are illustrated below.

(133) ##STR00021## ##STR00022##

(134) Among the partial structures of Formula (a), preferable specific examples are shown below.

(135) ##STR00023##

(136) Among the partial structures of Formula (a), more preferable specific examples are shown below.

(137) ##STR00024##

(138) Among the partial structures of Formula (a), particularly preferable specific examples are shown below.

(139) ##STR00025##

(140) B) When Het is a thienyl group, a thiazolyl group, an isothiazolyl group, a thiadiazolyl group or a thiatriazolyl group, Het represents a partial structure represented by Formula (b-1)

(141) ##STR00026##
or Formula (b-2)

(142) ##STR00027##
(wherein R3 is the same as defined hereinabove and “nb” represents an integer of 0 to 3).

(143) G6, G7 and G8 in Formula (b-1) and Formula (b-2) are each independent and represent a carbon atom or a nitrogen atom.

(144) “nb” in Formula (b-1) and Formula (b-2) represents an integer of 0 to 3.

(145) When “nb” in Formula (b-1) and Formula (b-2) is 2 or more, the two or more substituents R3 are independent of one another and may be selected appropriately to be the same as or different from one another.

(146) Specific examples of the partial structure of Formula (b-1) are shown below.

(147) ##STR00028##

(148) Among the partial structures of Formula (b-1), preferable specific examples are shown below.

(149) ##STR00029##

(150) Among the partial structures of Formula (b-1), more preferable specific examples are shown below.

(151) ##STR00030##

(152) Specific examples of the partial structure of Formula (b-2) are shown below.

(153) ##STR00031##

(154) Among the partial structures of Formula (b-2), preferable specific examples are shown below.

(155) ##STR00032##

(156) Among the partial structures of Formula (b-2), more preferable specific examples are shown below.

(157) ##STR00033##

(158) C) When Het is a pyrrolyl group, a pyrazolyl group, an imidazolyl group, a triazolyl group, a tetrazolyl group or a pentazolyl group, Het represents a partial structure represented by

(159) ##STR00034##
(wherein R3 is the same as defined hereinabove and “nc” represents an integer of 0 to 4).

(160) G9, G10, G11 and G12 in Formula (c-1), Formula (c-2) and Formula (c-3) are each independent and represent a carbon atom or a nitrogen atom.

(161) “nc” in Formula (c-1), Formula (c-2) and Formula (c-3) represents an integer of 0 to 4.

(162) When “nc” in Formula (c-1), Formula (c-2) and Formula (c-3) is 2 or more, the two or more substituents R3 are independent of one another and may be selected appropriately to be the same as or different from one another.

(163) Specific examples of the partial structure of Formula (c-1) are shown below.

(164) ##STR00035##

(165) Among the partial structures of Formula (c-1), preferable specific examples are shown below.

(166) ##STR00036##

(167) Among the partial structures of Formula (c-1), more preferable specific examples are shown below.

(168) ##STR00037##

(169) Among the partial structures of Formula (c-1), particularly preferable specific examples are shown below.

(170) ##STR00038##

(171) Specific examples of the partial structure of Formula (c-2) are shown below.

(172) ##STR00039##

(173) Among the partial structures of Formula (c-2), preferable specific examples are shown below.

(174) ##STR00040##

(175) Among the partial structures of Formula (c-2), more preferable specific examples are shown below.

(176) ##STR00041##

(177) Among the partial structures of Formula (c-2), particularly preferable specific examples are shown below.

(178) ##STR00042##

(179) Specific examples of the partial structure of Formula (c-3) are shown below.

(180) ##STR00043##

(181) Among the partial structures of Formula (c-3), preferable specific examples are shown below.

(182) ##STR00044##

(183) Among the partial structures of Formula (c-3), more preferable specific examples are shown below.

(184) ##STR00045##

(185) Among the partial structures of Formula (c-3), particularly preferable specific examples are shown below.

(186) ##STR00046##

(187) D) When Het is a furyl group or an oxazolyl group, Het represents a partial structure represented by Formula (d-1)

(188) ##STR00047##
or Formula (d-2)

(189) ##STR00048##
(wherein R3 is the same as defined hereinabove and “nd” represents an integer of 0 to 3).

(190) G13 and G14 in Formula (d-1) and Formula (d-2) are each independent and represent a carbon atom or a nitrogen atom.

(191) “nd” in Formula (d-1) and Formula (d-2) represents an integer of 0 to 3.

(192) When “nd” in Formula (d-1) and Formula (d-2) is 2 or more, the two or more substituents R3 are independent of one another and may be selected appropriately to be the same as or different from one another.

(193) Specific examples of the partial structure of Formula (d-1) are shown below.

(194) ##STR00049##

(195) Among the partial structures of Formula (d-1), preferable specific examples are shown below.

(196) ##STR00050##

(197) Among the partial structures of Formula (d-1), more preferable specific examples are shown below.

(198) ##STR00051##

(199) Specific examples of the partial structure of Formula (d-2) are shown below.

(200) ##STR00052##

(201) Among the partial structures of Formula (d-2), preferable specific examples are shown below.

(202) ##STR00053##

(203) E) When Het is an indolyl group, an isoindolyl group, an indazolyl group, a benzimidazolyl group or a benzotriazolyl group, Het represents a partial structure represented by Formula (e-1)

(204) ##STR00054##
or Formula (e-2)

(205) ##STR00055##
(wherein R3 is the same as defined hereinabove and “ne” represents an integer of 0 to 6).

(206) G15 and G16 in Formula (e-1) and Formula (e-2) are each independent and represent a carbon atom or a nitrogen atom.

(207) “ne” in Formula (e-1) and Formula (e-2) represents an integer of 0 to 6.

(208) When “ne” in Formula (e-1) and Formula (e-2) is 2 or more, the two or more substituents R3 are independent of one another and may be selected appropriately to be the same as or different from one another.

(209) Specific examples of the partial structure of Formula (e-1) are shown below.

(210) ##STR00056## ##STR00057##

(211) Specific examples of the partial structure of Formula (e-2) are shown below.

(212) ##STR00058##

(213) F) when Het is a benzofuryl group, an isobenzofuryl group or a benzoxazolyl group, Het represents a partial structure represented by Formula (f-1)

(214) ##STR00059##
or Formula (f-2)

(215) ##STR00060##
(wherein R3 is the same as defined hereinabove and “nf” represents an integer of 0 to 5).

(216) G17 in Formula (f-1) represents a carbon atom or a nitrogen atom.

(217) “nf” in Formula (f-1) and Formula (f-2) represents an integer of 0 to 5.

(218) When “nf” in Formula (f-1) and Formula (f-2) is 2 or more, the two or more substituents R3 are independent of one another and may be selected appropriately to be the same as or different from one another.

(219) Specific examples of the partial structure of Formula (f-1) are shown below.

(220) ##STR00061##

(221) Specific examples of the partial structure of Formula (f-2) are shown below.

(222) ##STR00062##

(223) G) When Het is a benzothienyl group, benzothiazolyl group, a benzisothiazolyl group or a benzothiadiazolyl group, Het represents a partial structure represented by Formula (g-1)

(224) ##STR00063##
or Formula (g-2)

(225) ##STR00064##
(wherein R3 is the same as defined hereinabove and “ng” represents an integer of 0 to 5).

(226) G18 and G19 in Formula (g-1) and Formula (g-2) are each independent and represent a carbon atom or a nitrogen atom.

(227) “ng” in Formula (g-1) and Formula (g-2) represents an integer of 0 to 5.

(228) When “ng” in Formula (g-1) and Formula (g-2) is 2 or more, the two or more substituents R3 are independent of one another and may be selected appropriately to be the same as or different from one another.

(229) Specific examples of the partial structure of Formula (g-1) are shown below.

(230) ##STR00065## ##STR00066##

(231) Specific examples of the partial structure of Formula (g-2) are shown below.

(232) ##STR00067##

(233) H) When Het is an indolidinyl group, an imidazopyridyl group, a pyrazolopyridyl group or a triazolopyridyl group, Het represents a partial structure represented by Formula (h-1)

(234) ##STR00068##
(wherein R3 is the same as defined hereinabove and “nh” represents an integer of 0 to 6).

(235) G20, G21 and G22 in Formula (h-1) are each independent and represent a carbon atom or a nitrogen atom.

(236) “nh” in Formula (h-1) represents an integer of 0 to 6.

(237) When “nh” in Formula (h-1) is 2 or more, the two or more substituents R3 are independent of one another and may be selected appropriately to be the same as or different from one another.

(238) Specific examples of the partial structure of Formula (h-1) are shown below.

(239) ##STR00069## ##STR00070## ##STR00071## ##STR00072##

(240) I) When Het is a pyrrolopyrimidinyl group, an imidazopyrimidinyl group, a pyrazolopyrimidinyl group, a triazolopyrimidinyl group, a pyrrolopyrazinyl group, an imidazopyrazinyl group, a pyrazolopyrazinyl group or a triazolopyrazinyl group, Het represents a partial structure represented by

(241) ##STR00073##
(wherein R3 is the same as defined hereinabove and “ni” represents an integer of 0 to 5).

(242) G23, G24 and G25 in Formula (i-1), Formula (i-2) and Formula (i-3) are each independent and represent a carbon atom or a nitrogen atom.

(243) “ni” in Formula (i-1), Formula (i-2) and Formula (i-3) represents an integer of 0 to 5.

(244) When “ni” in Formula (i-1), Formula (i-2) and Formula (i-3) is 2 or more, the two or more substituents R3 are independent of one another and may be selected appropriately to be the same as or different from one another.

(245) Specific examples of the partial structure of Formula (i-1) are shown below.

(246) ##STR00074## ##STR00075## ##STR00076##

(247) Specific examples of the partial structure of Formula (i-2) are shown below.

(248) ##STR00077## ##STR00078## ##STR00079## ##STR00080##

(249) Specific examples of the partial structure of Formula (i-3) are shown below.

(250) ##STR00081## ##STR00082## ##STR00083##

(251) J) When Het is a quinolyl group, an isoquinolyl group, a cinnolyl group, a phthalazinyl group, a quinoxalynyl group, a quinazolynyl group or a naphthylidinyl group, Het represents a partial structure represented by Formula (j-1)

(252) ##STR00084##
or Formula (j-2)

(253) ##STR00085##
(wherein R3 is the same as defined hereinabove and “nj” represents an integer of 0 to 6).

(254) G26, G27, G28 and G29 in Formula (j-1) and Formula (j-2) are each independent and represent a carbon atom or a nitrogen atom. With the proviso that at least one among G26, G27, G28 and G29 is a nitrogen atom. Preferred G26, G27, G28 and G29 are that any one of G26, G27, G28 and G29 is a nitrogen atom. That is, it is a quinolyl group.

(255) “nj” in Formula (j-1) and Formula (j-2) represents an integer of 0 to 6.

(256) When “nj” in Formula (j-1) and Formula (j-2) is 2 or more, the two or more substituents R3 are independent of one another and may be selected appropriately to be the same as or different from one another.

(257) Specific examples of the partial structures of Formula (j-1) are illustrated below.

(258) ##STR00086## ##STR00087## ##STR00088##

(259) Specific examples of the partial structures of Formula (j-2) are illustrated below.

(260) ##STR00089##

(261) N) When. Het is the “3 to 6 membered ring group containing 1 to 2 oxygen atoms”, Het represents a 1,2-epoxyethanyl group, an oxetanyl group, a oxolanyl group, an oxanyl group, a 1,3-dioxolanyl group, a 1,3-dioxanyl group or a 1,4-dioxanyl group. Above all, an oxolanyl group, an oxanyl group, a 1,3-dioxolanyl group, a 1,3-dioxanyl group or a 1,4-dioxanyl group is preferable, and in particular, a 1,3-dioxolanyl group or a 1,3-dioxanyl group is preferable.

(262) Y in Formula (1) represents a phenyl group, a pyridyl group, a pyridazinyl group, a pyrimidinyl group, a pyrazinyl group, a triazinyl group, a tetrazinyl group, a thienyl group, a thiazolyl group, an isothiazolyl group or a thiadiazolyl group. Above all, a phenyl group or a pyridyl group is preferable, and in particular, a phenyl group is preferable.

(263) The phenyl group is substituted with R4 at an ortho position and is further optionally substituted with 0 to 4 substituents R5. (with the proviso that when two or more substituents R5 are present, each R5 represents an independent substituent.)

(264) the pyridyl group, the pyridazinyl group, the pyrimidinyl group, the pyrazinyl group, the triazinyl group or the tetrazinyl group is substituted with R4 at an ortho position and is further optionally substituted with 0 to 3 substituents R5. (with the proviso that when two or more substituents R5 are present, each R5 represents an independent substituent.)

(265) the thienyl group, the thiazolyl group, the isothiazolyl group or the thiadiazolyl group is substituted with R4 at an ortho position and is further optionally substituted with 0 to 2 substituents R5. (with the proviso that when two substituents R5 are present, each R5 represents an independent substituent.)

(266) R4 in Formula (1) represents a hydroxyl group, a cyano group, a nitro group, a halogen atom, a C1-C6 alkyl group optionally substituted with substituent(s) C, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group optionally substituted with substituent(s) C, a C2-C6 alkenyl group optionally substituted with substituent(s) C, a C2-C6 haloalkenyl group, a C2-C6 alkynyl group optionally substituted with substituent(s) C, a C2-C6 haloalkynyl group, a C1-C6 alkoxy group optionally substituted with substituent(s) C, a C1-C6 haloalkoxy group, a C3-C8 cycloalkoxy group optionally substituted with substituent(s) C, a C2-C6 alkenyloxy group optionally substituted with substituent(s) C, a C2-C6 haloalkenyloxy group, a C3-C6 alkynyloxy group optionally substituted with substituent(s) C, a C3-C6 haloalkynyloxy group, an aryl group optionally substituted with substituent(s) D, a heteroaryl group optionally substituted with substituent(s) D, an aryloxy group optionally substituted with substituent(s) D, a heteroaryloxy group optionally substituted with substituent(s) D, an aralkyloxy group optionally substituted with substituent(s) D, RaRbN— (wherein Ra and Rb are the same as defined hereinabove), Rc-L- (wherein Rc and L are the same as defined hereinabove), Rx1C(═O)— (wherein Rx1 is the same as defined hereinabove), Rx1C(═O)O— (wherein Rx1 is the same as defined hereinabove), Rx2C(═O)N(Rx3)- (wherein Rx2 and Rx3 are the same as defined hereinabove), Rx4Rx5C═N—O— (wherein Rx4 and Rx5 are the same as defined hereinabove.) or a 3 to 6-membered ring group containing 1 to 2 oxygen atoms.

(267) Above all, R4 is preferably a cyano group, a nitro group, a halogen atom, a C1-C6 alkyl group optionally substituted with substituent(s) C, a C1-C6 haloalkyl group, a C1-C6 alkoxy group optionally substituted with substituent(s) C or C1-C6 haloalkoxy group;

(268) R4 is particularly preferably a cyano group, a nitro group, a halogen atom, a C1-C6 alkyl group optionally substituted with substituent(s) C, a C1-C6 haloalkyl group or a C1-C6 alkoxyl group optionally substituted with substituent(s) C;

(269) and R4 is further preferably a cyano group, a halogen atom, a C1-C6 alkyl group optionally substituted with substituent(s) C, a C1-C6 haloalkyl group or a C1-C6 alkoxyl group optionally substituted with substituent(s) C.

(270) In R4 of Formula (1), a hydroxyl group, a cyano group and a nitro group are contained.

(271) The halogen atom in R4 of Formula (1) is the same as defined hereinabove, preferably a fluorine atom, a chlorine atom, a bromine atom or an iodine atom, and further preferably a fluorine atom, a chlorine atom or a bromine atom.

(272) The C1-C6 alkyl group of the “C1-C6 alkyl group optionally substituted with substituent(s) C” in R4 of Formula (1) is the same as defined hereinabove, preferably a methyl group, an ethyl group, a propyl group or an isopropyl group, further preferably a methyl group, an ethyl group or a propyl group, and particularly preferably a methyl group or an ethyl group. When it has the substituent(s) C, the C1-C6 alkyl group is optionally substituted with the substituent(s) C in place of hydrogen atom(s).

(273) The “C1-C6 haloalkyl group” in R4 of Formula (1) is the same as defined hereinabove, preferably a difluoromethyl group, a trifluoromethyl group, a 2,2-difluoroethyl group, a 2,2,2-trifluoroethyl group, a 3,3-difluoropropyl group or a 3,3,3-trifluoropropyl group, further preferably a difluoromethyl group or a trifluoromethyl group, and particularly preferably a trifluoromethyl group.

(274) The C3-C8 cycloalkyl group of the “C3-C8 cycloalkyl group optionally substituted with substituent(s) C” in R4 of Formula (1) is the same as defined hereinabove, preferably a cyclopropyl group, a cyclobutyl group, a cyclopentyl group or a cyclohexyl group, and further preferably a cyclopropyl group or a cyclobutyl group. When it has the substituent(s) C, the C3-C8 cycloalkyl group is optionally substituted with the substituent(s) C in place of hydrogen atom(s).

(275) The C2-C6 alkenyl group of the “C2-C6 alkenyl group optionally substituted with substituent(s) C” in R4 of Formula (1) is the same as defined hereinabove, preferably a vinyl group, a 1-propenyl group, an allyl group, a 1-butenyl group, a 2-butenyl group or a 3-butenyl group, and further preferably a vinyl group. When it has the substituent(s) C, the C2-C6 alkenyl group is optionally substituted with the substituent(s) C in place of hydrogen atom(s).

(276) The “C2-C6 haloalkenyl group” in R4 of Formula (1) is the same as defined hereinabove, preferably a 2-fluorovinyl group, a 2,2-difluorovinyl group, a 2,2-dichlorovinyl group, a 3-fluoroallyl group, a 3,3-difluoroallyl group or a 3,3-dichloroallyl group, and further preferably a 2-fluorovinyl group or a 2,2-difluorovinyl group.

(277) The C2-C6 alkynyl group of the “C2-C6 alkynyl group optionally substituted with substituent(s) C” in R4 of Formula (1) is the same as defined hereinabove, preferably an ethynyl group, a 1-propynyl group or a propargyl group, and further preferably a ethynyl group. When it has the substituent(s) C, the C2-C6 alkynyl group is optionally substituted with the substituent(s) C in place of hydrogen atom(s).

(278) The “C2-C6 haloalkynyl group” in R4 of Formula (1) is the same as defined hereinabove, preferably a 3,3-difluoro-1-propynyl group, a 3,3,3-trifluoro-1-propynyl group, a 4,4-difluoro-1-butynyl group, a 4,4-difluoro-2-butynyl group, a 4,4,4-trifluoro-1-butynyl group or a 4,4,4-trifluoro-2-butynyl group, and further preferably a 3,3-difluoro-1-propynyl group or a 3,3,3-trifluoro-1-propynyl group.

(279) The C1-C6 alkoxy group of the “C1-C6 alkoxyl group optionally substituted with substituent(s) C” in R4 of Formula (1) is the same as defined hereinabove, preferably a methoxy group, an ethoxy group, a propyloxy group or an isopropyloxy group, further preferably a methoxy group or an ethoxy group, and particularly preferably a methoxy group. When it has the substituent(s) C, the C1-C6 alkoxy group is optionally substituted with the substituent(s) C in place of hydrogen atom(s).

(280) The “C1-C6 haloalkoxy group” in R4 of Formula (1) is the same as defined hereinabove, preferably a difluoromethoxy group, a trifluoromethoxy group, a 2,2-difluoroethoxy group, a 2,2,2-trifluoroethoxy group, a 3,3-difluoropropyloxy group or a 3,3,3-trifluoropropyloxy group, and further preferably a difluoromethoxy group or a trifluoromethoxy group.

(281) The C3-C8 cycloalkoxy group of the “C3-C8 cycloalkoxy group optionally substituted with substituent(s) C” in R4 of Formula (1) is the same as defined hereinabove, preferably a cyclopropyloxy group, a cyclobutoxy group, a cyclopentyloxy group or a cyclohexyloxy group, and further preferably a cyclopropyloxy group or a cyclobutoxy group. When it has the substituent(s) C, the C3-C8 cycloalkoxy group is optionally substituted with the substituent(s) C in place of hydrogen atom(s).

(282) The C2-C6 alkenyloxy group of the “C2-C6 alkenyloxy group optionally substituted with substituent(s) C” in R4 of Formula (1) is the same as defined hereinabove, preferably a vinyloxy group, a 1-propenyloxy group or an allyloxy group, and further preferably an allyloxy group. When it has the substituent(s) C, the C2-C6 alkenyloxy group is optionally substituted with the substituent(s) C in place of hydrogen atom(s).

(283) The “C2-C6 haloalkenyloxy group” in R4 of Formula (1) is the same as defined hereinabove, preferably a 2-fluorovinyloxy group, a 2,2-difluorovinyloxy group, a 2,2-dichlorovinyloxy group, a 3-fluoroallyloxy group, a 3,3-difluoroallyloxy group or a 3,3-dichloroallyloxy group, and further preferably a 2-fluorovinyloxy group or a 2,2-difluorovinyloxy group.

(284) The C3-C6 alkynyloxy group of the “C3-C6 alkynyloxy group optionally substituted with substituent(s) C” in R4 of Formula (1) is the same as defined hereinabove, preferably a propargyloxy group, a 2-butynyloxy group or a 3-butynyloxy group, and further preferably a propargyloxy group. When it has the substituent(s) C, the C3-C6 alkynyloxy group is optionally substituted with the substituent(s) C in place of hydrogen atom(s).

(285) The “C3-C6 haloalkynyloxy group” in R4 of Formula (1) is the same as defined hereinabove, preferably a 4,4-difluoro-2-butynyloxy group, a 4-chloro-4,4-difluoro-2-butynyloxy group, a 4-bromo-4,4-difluoro-2-butynyloxy group or a 4,4,4-trifluoro-2-butynyloxy group, and further preferably a 4,4-difluoro-2-butynyloxy group or a 4,4,4-trifluoro-2-butynyloxy group.

(286) The aryl group of the “aryl group optionally substituted with substituent(s) D” in R4 of Formula (1) is the same as defined hereinabove, and preferably a phenyl group. When it has the substituent(s) D, the aryl group is optionally substituted with the substituent(s) D in place of hydrogen(s).

(287) The heteroaryl group of the “heteroaryl group optionally substituted with substituent(s) D” in R4 of Formula (1) is the same as defined hereinabove, preferably a pyridyl group, a pyrazinyl group, a thienyl group, a thiazolyl group, an isothiazolyl group, furyl group, an imidazolyl group, a pyrazolyl group, oxazolyl group, an isoxazolyl group, a triazolyl group, an oxadiazolyl group or a tetrazolyl group, and further preferably a pyridyl group, an imidazolyl group, a pyrazolyl group, triazolyl group or a tetrazolyl group. When it has the substituent(s) D, the heteroaryl group is optionally substituted with the substituent(s) D in place of hydrogen(s).

(288) The aryloxy group of the “aryloxy group optionally substituted with substituent(s) D” in R4 of Formula (1) is the same as defined hereinabove, preferably a phenoxy group or a naphthyloxy group, and further preferably a phenoxy group. When it has the substituent(s) D, the aryloxy group is optionally substituted with the substituent(s) D in place of hydrogen atom(s).

(289) The heteroaryloxy group of the “heteroaryloxy group optionally substituted with substituent(s) D” in R4 of Formula (1) is the same as defined hereinabove, preferably a pyridyloxy group, a pyridazinyloxy group, a pyrimidinyloxy group, a pyrazinyloxy group, a pyrazolyloxy group, a triazinyloxy group, a tetrazinyloxy group, a thienyloxy group, a thiazolyloxy group, an isothiazolyloxy group or a thiadiazolyloxy group, and further preferably a pyridyloxy group, a pyridazinyloxy group, a pyrimidinyloxy group, a pyrazinyloxy group or a pyrazolyloxy group. When it has the substituent(s) D, the heteroaryloxy group is optionally substituted with the substituent(s) D in place of hydrogen atom(s).

(290) The aralkyloxy group of the “aralkyloxy group optionally substituted with substituent(s) D” in R4 of Formula (1) is the same as defined hereinabove, preferably a benzyloxy group, a phenethyloxy group or a phenylpropyloxy group, and further preferably a benzyloxy group. When it has the substituent(s) D, the aralkyloxy group is optionally substituted with the substituent(s) D in place of hydrogen atom(s).

(291) Ra and Rb of “RaRbN—” in R4 of Formula (1) are the same as defined hereinabove. The “RaRbN—” is preferably an amino group, a methylamino group, an ethylamino group, a (methoxymethyl)amino group, a (2-methoxyethyl)amino group, a (cyanomethyl)amino group, a (2-cyanoethyl)amino group, a dimethylamino group, an ethylmethylamino group, a diethylamino group, a (methoxymethyl)methylamino group, a (2-methoxyethyl)methylamino group, a (cyanomethyl)methylamino group, a (2-cyanoethyl)methylamino group, a 2,2-difluoroethylamino group, a 2,2,2-trifluoroethylamino group, a cyclopropylamino group, a (cyclopropyl)methylamino group, a pyrrolidinyl group or a piperidinyl group, and further preferably an amino group, a dimethylamino group, an ethylmethylamino group or a diethylamino group.

(292) Rc and L of the “Rc-L-” in R4 of Formula (1) is the same as defined hereinabove. The “Rc-L-” is preferably a methylthio group, a methanesulfinyl group, a methanesulfonyl group, a trifluoromethylthio group, a trifluoromethanesulfinyl group or a trifluoromethanesulfonyl group, and further preferably a methylthio group, a methanesulfinyl group or a methanesulfonyl group.

(293) Rx1 of the “Rx1C(═O)—” in R4 of Formula (1) is the same as defined hereinabove. The “Rx1C(═O)—” is preferably an acetyl group, a methoxyacetyl group, a cyanoacetyl group, a propionyl group, a difluoroacetyl group, a trifluoroacetyl group, a cyclopropancarbonyl group, a methoxycarbonyl group, an ethoxycarbonyl group, a 2,2-difluoroethoxycarbonyl group, a 2,2,2-trifluoroethoxycarbonyl group, a 3,3,3-trifluoropropyloxycarbonyl group, a cyclopropyloxycarbonyl group, an aminocarbonyl group, a methylaminocarbonyl group, an ethylaminocarbonyl group, a (methoxymethyl)aminocarbonyl group, a (2-methoxyethyl)aminocarbonyl group, a (cyanomethyl)aminocarbonyl group, a (2-cyanoethyl)aminocarbonyl group, a dimethyl-aminocarbonyl group, an ethylmethylaminocarbonyl group, a diethylaminocarbonyl group, a (methoxymethyl)methylaminocarbonyl group, a (2-methoxyethyl)methylaminocarbonyl group, a (cyanomethyl)methylaminocarbonyl group, a (2-cyanoethyl)methylaminocarbonyl group, a 2,2-difluoroethylaminocarbonyl group, a 2,2,2-trifluoroethylaminocarbonyl group, a cyclopropylaminocarbonyl group, a (cyclopropyl)methylaminocarbonyl group, a pyrrolidinylcarbonyl group or a piperidinylcarbonyl group, and further preferably an acetyl group, a methoxyacetyl group, a cyanoacetyl group, a difluoroacetyl group, a trifluoroacetyl group, a methoxycarbonyl group, an ethoxycarbonyl group, an aminocarbonyl group, a dimethylaminocarbonyl group, an ethylmethylaminocarbonyl group or a diethylaminocarbonyl group.

(294) Rx1 of “Rx1C(═O)O—” in R4 of Formula (1) is the same as defined hereinabove. The “Rx1C(═O)O—” is preferably an acetyloxy group, a methoxyacetyloxy group, a cyanoacetyloxy group, a propionyloxy group, a difluoroacetyloxy group, a trifluoroacetyloxy group, a cyclopropancarbonyloxy group, a methoxycarbonyloxy group, an ethoxycarbonyloxy group, a 2,2-difluoroethoxycarbonyloxy group, a 2,2,2-trifluoroethoxycarbonyloxy group, a 3,3,3-trifluoropropyloxycarbonyloxy group, a cyclopropyloxycarbonyloxy group, an aminocarbonyloxy group, a methylaminocarbonyloxy group, an ethylaminocarbonyloxy group, a (methoxymethyl)-aminocarbonyloxy group, a (2-methoxyethyl)aminocarbonyloxy group, a (cyano-methyl)aminocarbonyloxy group, a (2-cyanoethyl)aminocarbonyloxy group, a dimethylaminocarbonyloxy group, an ethylmethylaminocarbonyloxy group, a diethylaminocarbonyloxy group, a (methoxymethyl)methylaminocarbonyloxy group, a (2-methoxyethyl)methylaminocarbonyloxy group, a (cyanomethyl)methylamino-carbonyloxy group, a (2-cyanoethyl)methylaminocarbonyloxy group, a 2,2-difluoroethylaminocarbonyloxy group, a 2,2,2-trifluoroethylaminocarbonyloxy group, a cyclopropylaminocarbonyloxy group, a (cyclopropyl)methylaminocarbonyloxy group, a pyrrolidinylcarbonyloxy group or a piperidinylcarbonyloxy group, further preferably an acetyloxy group, a methoxyacetyloxy group, a cyanoacetyloxy group, a difluoroacetyloxy group, a trifluoroacetyloxy group, a methoxycarbonyloxy group, an ethoxycarbonyloxy group, an aminocarbonyloxy group, a dimethylaminocarbonyloxy group, an ethylmethylaminocarbonyloxy group or a diethylaminocarbonyloxy group.

(295) Each term of “Rx2C(═O)N(Rx3)-” (wherein Rx2 represents a hydrogen atom, a C1-C6 alkyl group optionally substituted with substituent(s) B, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C3-C8 cycloalkoxy group or RaRbN— (wherein Ra and Rb are the same as defined hereinabove), Rx3 represents a hydrogen atom, a C1-C6 alkyl group optionally substituted with substituent(s) B, a C1-C6 haloalkyl group or a C3-C8 cycloalkyl group.) in R4 of Formula (1) is the same as defined hereinabove. Incidentally, with regard to the “C1-C6 alkyl group optionally substituted with substituent(s) B”, when it has the substituent(s) B, the C1-C6 alkyl group is optionally substituted with the substituent(s) B in place of hydrogen atom(s). The Rx2 is preferably a hydrogen atom, a methyl group, a methoxymethyl group, a cyanomethyl group, an ethyl group, a difluoromethyl group, a trifluoromethyl group, a cyclopropyl group, a methoxy group, an ethoxy group, a 2,2-difluoroethoxy, a 2,2,2-trifluoroethoxy group, a cyclopropyloxy group, an amino group, a methylamino group, an ethylamino group, a (methoxymethyl)amino group, a (2-methoxyethyl)amino group, a (cyanomethyl)amino group, a (2-cyanoethyl)amino group, a dimethylamino group, an ethylmethylamino group, a diethylamino group, a (methoxymethyl)methylamino group, a (2-methoxyethyl)methylamino group, a (cyanomethyl)methylamino group, a (2-cyanoethyl)methylamino group, a 2,2-difluoroethylamino group, a 2,2,2-trifluoroethylamino group, a cyclopropylamino group, a (cyclopropyl)methylamino group, a pyrrolidinyl group or a piperidinyl group, and further preferably a hydrogen atom, a methyl group, a methoxymethyl group, a cyanomethyl group, a difluoromethyl group, a trifluoromethyl group, a methoxy group, an ethoxy group, an amino group, a dimethylamino group, an ethylmethylamino group or a diethylamino group. Also, the Rx3 is preferably a hydrogen atom, a methyl group, a methoxymethyl group, an ethoxymethyl group, a cyanomethyl group, an ethyl group, a 2-methoxyethyl group, a 2-ethoxyethyl group, a 2-cyanoethyl group, a propyl group, a 2,2-difluoroethyl group, a 2,2,2-trifluoroethyl group or a cyclopropyl group, and further preferably a hydrogen atom, a methyl group, a methoxymethyl group, a cyanomethyl group, an ethyl group, a 2-methoxyethyl group, a 2,2-difluoroethyl group or a 2,2,2-trifluoroethyl group.

(296) Each term in the “Rx4Rx5C═N—O—” (wherein Rx4 and Rx5 each independently represent a hydrogen atom, a C1-C6 alkyl group optionally substituted with substituent(s) B, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C3-C8 cycloalkoxy group or RaRbN— (wherein Ra and Rb are the same as defined hereinabove)) in R4 of Formula (1) is the same as defined hereinabove. Incidentally, with regard to the “C1-C6 alkyl group optionally substituted with substituent(s) B”, when it has the substituent(s) B, the C1-C6 alkyl group is optionally substituted with the substituent(s) B in place of hydrogen atom(s).

(297) Rx4 and Rx5 are each preferably a methyl group, an ethyl group, a propyl group, an isopropyl group, a trifluoromethyl group, a 2,2,2-trifluoroethyl group, a cyclopropyl group, a cyclopentyl group, a cyclohexyl group, a methoxy group, an ethoxy group, isopropyloxy group, a difluoromethoxy group, a trifluoromethoxy group, a 2,2-difluoroethoxy group, a 2,2,2-trifluoroethoxy group, a cyclopropyloxy group, a cyclobutyloxy group, a cyclopentyloxy group, an amino group, a methylamino group, an ethylamino group, a (methoxymethyl)amino group, a (2-methoxyethyl)amino group, a (cyanomethyl)amino group, a (2-cyanoethyl)amino group, a dimethylamino group, an ethylmethylamino group, a diethylamino group, a (methoxymethyl)methylamino group, a (2-methoxyethyl)methylamino group, a (cyanomethyl)methylamino group, a (2-cyanoethyl)methylamino group, a 2,2-difluoroethylamino group, a 2,2,2-trifluoroethylamino group, a cyclopropylamino group, a (cyclopropyl)methylamino group, a pyrrolidinyl group or a piperidinyl group, and further preferably a methyl group, an ethyl group, a trifluoromethyl group, a 2,2,2-trifluoroethyl group, a methoxy group, an ethoxy group, a 2,2,2-trifluoroethoxy group, a dimethylamino group, an ethylmethylamino group or a diethylamino group.

(298) The “3 to 6 membered ring group containing 1 to 2 oxygen atoms” in R4 of Formula (1) is the same as defined hereinabove, preferably an oxolanyl group, an oxanyl group, a 1,3-dioxolanyl group or a 1,3-dioxanyl group, and further preferably a 1,3-dioxolanyl group or a 1,3-dioxanyl group.

(299) R5 in Formula (1) is defined the same as R4 described hereinabove. That is, it represents a hydroxyl group, a cyano group, a nitro group, a halogen atom, a C1-C6 alkyl group optionally substituted with substituent(s) C, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group optionally substituted with substituent(s) C, a C2-C6 alkenyl group optionally substituted with substituent(s) C, a C2-C6 haloalkenyl group, a C2-C6 alkynyl group optionally substituted with substituent(s) C, a C2-C6 haloalkynyl group, a C1-C6 alkoxy group optionally substituted with substituent(s) C, a C1-C6 haloalkoxy group, a C3-C8 cycloalkoxy group optionally substituted with substituent(s) C, a C2-C6 alkenyloxy group optionally substituted with substituent(s) C, a C2-C6 haloalkenyloxy group, a C3-C6 alkynyloxy group optionally substituted with substituent(s) C, a C3-C6 haloalkynyloxy group, an aryl group optionally substituted with substituent(s) D, a heteroaryl group optionally substituted with substituent(s) D, an aryloxy group optionally substituted with substituent(s) D, a heteroaryloxy group optionally substituted with substituent(s) D, an aralkyloxy group optionally substituted with substituent(s) D, RaRbN— (wherein Ra and Rb are the same as defined hereinabove), Rc-L- (wherein Rc and L are the same as defined hereinabove), Rx1C(═O)— (wherein Rx1 is the same as defined hereinabove), Rx C(═O)O— (wherein Rx1 is the same as defined hereinabove), Rx2C(═O)N(Rx3)- (wherein Rx2 and Rx3 are the same as defined hereinabove), Rx4Rx5C═N—O— (wherein Rx4 and Rx5 are the same as defined hereinabove.) or a 3 to 6-membered ring group containing 1 to 2 oxygen atoms.

(300) Above all, R5 is preferably a hydroxyl group, a cyano group, a halogen atom, a C1-C6 alkyl group optionally substituted with substituent(s) C, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group optionally substituted with substituent(s) C, a C2-C6 alkenyl group optionally substituted with substituent(s) C, a C2-C6 alkynyl group optionally substituted with substituent(s) C, a C1-C6 alkoxy group optionally substituted with substituent(s) C, a C1-C6 haloalkoxy group, a C3-C8 cycloalkoxy group optionally substituted with substituent(s) C, a C2-C6 alkenyloxy group optionally substituted with substituent(s) C, a C3-C6 alkynyloxy group optionally substituted with substituent(s) C, RaRbN— (wherein Ra and Rb are the same as defined hereinabove), Rc-L- (wherein Rc and L are the same as defined hereinabove.) or Rx1C(═O)O— (wherein Rx1 is the same as defined hereinabove);

(301) R5 is particularly preferably a hydroxyl group, a cyano group, a halogen atom, a C1-C6 alkyl group optionally substituted with substituent(s) C, a C1-C6 alkoxy group optionally substituted with substituent(s) C, a C2-C6 alkenyloxy group optionally substituted with substituent(s) C, a C3-C6 alkynyloxy group optionally substituted with substituent(s) C, RaRbN— (wherein Ra and Rb are the same as defined hereinabove), Rc-L- (wherein Rc and L are the same as defined hereinabove.) or Rx1C(═O)O— (wherein Rx1 is the same as defined hereinabove);

(302) and R5 is further preferably a hydroxyl group, a cyano group, a halogen atom, a C1-C6 alkoxy group optionally substituted with substituent(s) C, a C2-C6 alkenyloxy group optionally substituted with substituent(s) C, a C3-C6 alkynyloxy group optionally substituted with substituent(s) C, RaRbN— (wherein Ra and Rb are the same as defined hereinabove), Rc-L- (wherein Rc and L are the same as defined hereinabove.) or Rx1C(═O)O— (wherein Rx1 is the same as defined hereinabove).

(303) In R5 of Formula (1), a hydroxyl group, a cyano group and a nitro group are contained.

(304) The halogen atom in R5 of Formula (1) is the same as defined hereinabove, preferably a fluorine atom, a chlorine atom, a bromine atom or an iodine atom, and further preferably a fluorine atom or an iodine atom.

(305) The C1-C6 alkyl group of the “C1-C6 alkyl group optionally substituted with substituent(s) C” in R5 of Formula (1) is the same as defined hereinabove, preferably a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group or an isobutyl group, further preferably a methyl group or an ethyl group. When it has the substituent(s) C, the C1-C6 alkyl group is optionally substituted with the substituent(s) C in place of hydrogen atom(s).

(306) The “C1-C6 haloalkyl group” in R5 of Formula (1) is the same as defined hereinabove, preferably a difluoromethyl group, a trifluoromethyl group, a 2,2-difluoroethyl group, a 2,2,2-trifluoroethyl group, a 3,3-difluoropropyl group or a 3,3,3-trifluoropropyl group, and further preferably a difluoromethyl group, a trifluoromethyl group, a 2,2-difluoroethyl group or a 2,2,2-trifluoroethyl group.

(307) The C3-C8 cycloalkyl group of the “C3-C8 cycloalkyl group optionally substituted with substituent(s) C” in R5 of Formula (1) is the same as defined hereinabove, preferably a cyclopropyl group, a cyclobutyl group, a cyclopentyl group or a cyclohexyl group, and further preferably a cyclopropyl group or a cyclobutyl group. When it has the substituent(s) C, the C3-C8 cycloalkyl group is optionally substituted with the substituent(s) C in place of hydrogen atom(s).

(308) The C2-C6 alkenyl group in the “C2-C6 alkenyl group optionally substituted with substituent(s) C” in R5 of Formula (1) is the same as defined hereinabove, preferably a vinyl group, a 1-propenyl group, an allyl group, a 1-butenyl group, a 2-butenyl group or a 3-butenyl group, and further preferably a vinyl group, a 1-propenyl group or an allyl group. When it has the substituent(s) C, C2-C6 alkenyl group is optionally substituted with the substituent(s) C in place of hydrogen atom(s).

(309) The “C2-C6 haloalkenyl group” in R5 of Formula (1) is the same as defined hereinabove, preferably a 2-fluorovinyl group, a 2,2-difluorovinyl group, a 2,2-dichlorovinyl group, a 3-fluoroallyl group, a 3,3-difluoroallyl group or a 3,3-dichloroallyl group, and further preferably a 2-fluorovinyl group or a 2,2-difluorovinyl group.

(310) The C2-C6 alkynyl group of the “C2-C6 alkynyl group optionally substituted with substituent(s) C” in R5 of Formula (1) is the same as defined hereinabove, preferably an ethynyl group, a 1-propynyl group, a propargyl group, a 1-butynyl group, a 2-butynyl group or a 3-butynyl group, and further preferably an ethynyl group, a 1-propynyl group or a propargyl group. When it has the substituent(s) C, the C2-C6 alkynyl group is optionally substituted with the substituent(s) C in place of hydrogen atom(s).

(311) The “C2-C6 haloalkynyl group” in R5 of Formula (1) is the same as defined hereinabove, preferably a 3,3-difluoro-1-propynyl group, a 3,3,3-trifluoro-1-propynyl group, a 4,4-difluoro-1-butynyl group, a 4,4-difluoro-2-butynyl group, a 4,4,4-trifluoro-1-butynyl group or a 4,4,4-trifluoro-2-butynyl group, and further preferably a 3,3-difluoro-1-propynyl group or a 3,3,3-trifluoro-1-propynyl group.

(312) The C1-C6 alkoxy group in the “C1-C6 alkoxyl group optionally substituted with substituent(s) C” in R5 of Formula (1) is the same as defined hereinabove, preferably a methoxy group, an ethoxy group, a propyloxy group, an isopropyloxy group, a butoxy group or an isobutoxy group, further preferably a methoxy group, an ethoxy group, a propyloxy group or an isopropyloxy group, and particularly preferably a methoxy group or an ethoxy group. When it has the substituent(s) C, the C1-C6 alkoxy group is optionally substituted with the substituent(s) C in place of hydrogen atom(s). The substituent(s) C is preferably a cyano group, a C3-C8 cycloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C2-C6 alkoxyalkoxy group, Rc-L- (wherein Rc and L are the same as defined hereinabove), Rx1C(═O)— (wherein Rx1 is the same as defined hereinabove.) or a 3 to 6-membered ring group containing 1 to 2 oxygen atoms, and further preferably a cyano group, a C1-C6 alkoxy group or Rc-L- (wherein Rc and L are the same as defined hereinabove). The C1-C6 alkoxy group substituted with the substituent(s) C is preferably a cyanomethoxy group, a cyanoethoxy group, a methoxymethoxy group, a methoxyethoxy group, an ethoxymethoxy group or an ethoxyethoxy group, further preferably a cyanomethoxy group, a methoxymethoxy group or a methoxyethoxy group, and particularly preferably a methoxymethoxy group or a methoxyethoxy group.

(313) The “C1-C6 haloalkoxy group” in R5 of Formula (1) is the same as defined hereinabove, preferably a difluoromethoxy group, a trifluoromethoxy group, a 2,2-difluoroethoxy group, a 2,2,2-trifluoroethoxy group, a 3,3-difluoropropyloxy group or a 3,3,3-trifluoropropyloxy group, and further preferably a difluoromethoxy group, a trifluoromethoxy group, a 2,2-difluoroethoxy group or a 2,2,2-trifluoroethoxy group.

(314) The C3-C8 cycloalkoxy group of the “C3-C8 cycloalkoxy group optionally substituted with substituent(s) C” in R5 of Formula (1) is the same as defined hereinabove, preferably a cyclopropyloxy group, a cyclobutoxy group, a cyclopentyloxy group or a cyclohexyloxy group, and further preferably a cyclopropyloxy group or a cyclobutoxy group. When it has the substituent(s) C, the C3-C8 cycloalkoxy group is optionally substituted with the substituent(s) C in place of hydrogen atom(s).

(315) The C2-C6 alkenyloxy group of the “C2-C6 alkenyloxy group optionally substituted with substituent(s) C” in R5 of Formula (1) is the same as defined hereinabove, preferably a vinyloxy group, a 1-propenyloxy group, an allyloxy group, a 1-butenyloxy group, a 2-butenyloxy group or a 3-butenyloxy group, further preferably a vinyloxy group, a 1-propenyloxy group or an allyloxy group, and particularly preferably an allyloxy group. When it has the substituent(s) C, the C2-C6 alkenyloxy group is optionally substituted with the substituent(s) C in place of hydrogen atom(s).

(316) The “C2-C6 haloalkenyloxy group” in R5 of Formula (1) is the same as defined hereinabove, preferably a 2-fluorovinyloxy group, a 2,2-difluorovinyloxy group, a 2,2-dichlorovinyloxy group, a 3-fluoroallyloxy group, a 3,3-difluoroallyloxy group or a 3,3-dichloroallyloxy group, and further preferably a 2-fluorovinyloxy group or a 2,2-difluorovinyloxy group.

(317) The C3-C6 alkynyloxy group of the “C3-C6 alkynyloxy group optionally substituted with substituent(s) C” in R5 of Formula (1) is the same as defined hereinabove, preferably a propargyloxy group, a 2-butynyloxy group or a 3-butynyloxy group, further preferably a propargyloxy group or a 2-butynyloxy group, and particularly preferably a propargyloxy group. When it has the substituent(s) C, the C3-C6 alkynyloxy group is optionally substituted with the substituent(s) C in place of hydrogen atom(s).

(318) The “C3-C6 haloalkynyloxy group” in R5 of Formula (1) is the same as defined hereinabove, preferably a 4,4-difluoro-2-butynyloxy group, a 4-chloro-4,4-difluoro-2-butynyloxy group, a 4-bromo-4,4-difluoro-2-butynyloxy group or a 4,4,4-trifluoro-2-butynyloxy group, and further preferably a 4,4-difluoro-2-butynyloxy group or a 4,4,4-trifluoro-2-butynyloxy group.

(319) The aryl group of the “aryl group optionally substituted with substituent(s) D” in R5 of Formula (1) is the same as defined hereinabove, and preferably a phenyl group. When it has, the substituent(s) D, the aryl group is optionally substituted with the substituent(s) D in place of hydrogen(s).

(320) The heteroaryl group of the “heteroaryl group optionally substituted with substituent(s) D” in R5 of Formula (1) is the same as defined hereinabove, preferably a pyridyl group, a pyrazinyl group, a thienyl group, a thiazolyl group, an isothiazolyl group, furyl group, an imidazolyl group, a pyrazolyl group, oxazolyl group, an isoxazolyl group, a triazolyl group, an oxadiazolyl group or a tetrazolyl group, and further preferably a pyridyl group, an imidazolyl group, a pyrazolyl group, triazolyl group or a tetrazolyl group. When it has the substituent(s) D, the heteroaryl group is optionally substituted with the substituent(s) D in place of hydrogen(s).

(321) The aryloxy group of the “aryloxy group optionally substituted with substituent(s) D” in R5 of Formula (1) is the same as defined hereinabove, preferably a phenoxy group or a naphthyloxy group, and further preferably a phenoxy group. When it has the substituent(s) D, the aryloxy group is optionally substituted with the substituent(s) D in place of hydrogen atom(s).

(322) The heteroaryloxy group of the “heteroaryloxy group optionally substituted with substituent(s) D” in R5 of Formula (1) is the same as defined hereinabove, preferably a pyridyloxy group, a pyridazinyloxy group, a pyrimidinyloxy group, a pyrazinyloxy group, a pyrazolyloxy group, a triazinyloxy group, a tetrazinyloxy group, a thienyloxy group, a thiazolyloxy group, an isothiazolyloxy group or a thiadiazolyloxy group, and further preferably a pyridyloxy group, a pyridazinyloxy group, a pyrimidinyloxy group, a pyrazinyloxy group or a pyrazolyloxy group. When it has the substituent(s) D, the heteroaryloxy group is optionally substituted with the substituent(s) D in place of hydrogen atom(s).

(323) The aralkyloxy group of the “aralkyloxy group optionally substituted with substituent(s) D” in R5 of Formula (1) is the same as defined hereinabove, preferably a benzyloxy group, a phenethyloxy group or a phenylpropyloxy group, and further preferably a benzyloxy group or a phenethyloxy group. When it has the substituent(s) D, the aralkyloxy group is optionally substituted with the substituent(s) D in place of hydrogen atom(s).

(324) Ra and Rb of the “RaRbN—” in R5 of Formula (1) are the same as defined hereinabove. Ra and Rb are each preferably a hydrogen atom, a C1-C6 alkyl group optionally substituted with substituent(s) B, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group, pyrrolidinyl group or a piperidinyl group, and further preferably a hydrogen atom, a C1-C6 alkyl group optionally substituted with substituent(s) B, a pyrrolidinyl group or a piperidinyl group. The “RaRbN—” is-preferably an amino group, a methylamino group, an ethylamino group, a (methoxymethyl)amino group, a (2-methoxyethyl)amino group, a (cyanomethyl)amino group, a (2-cyanoethyl)amino group, a dimethylamino group, an ethylmethylamino group, a diethylamino group, a (methoxymethyl)methylamino group, a (2-methoxyethyl)methylamino group, a (cyanomethyl)methylamino group, a (2-cyanoethyl)methylamino group, a 2,2-difluoroethylamino group, a 2,2,2-trifluoroethylamino group, a cyclopropylamino group, a (cyclopropyl)methylamino group, a pyrrolidinyl group or a piperidinyl group, further preferably an amino group, a methylamino group, a dimethylamino group, an ethylmethylamino group, a diethylamino group, a pyrrolidinyl group or a piperidinyl group, and particularly preferably a methylamino group, a pyrrolidinyl group or a piperidinyl group.

(325) Rc and L of the “Rc-L-” in R5 of Formula (1) is the same as defined hereinabove. The Rc is preferably a C1-C6 alkyl group. The L is preferably S. The “Rc-L-” is preferably a methylthio group, a methanesulfinyl group, a methanesulfonyl group, a trifluoromethylthio group, a trifluoromethanesulfinyl group or a trifluoromethanesulfonyl group, further preferably a methylthio group, a methanesulfinyl group or a methanesulfonyl group, and particularly preferably a methylthio group.

(326) Rx1 in the “Rx1C(═O)—” in R5 of Formula (1) is the same as defined hereinabove. The “Rx1C(═O)—” is preferably an acetyl group, a methoxyacetyl group, a cyanoacetyl group, a propionyl group, a difluoroacetyl group, a trifluoroacetyl group, a cyclopropancarbonyl group, a methoxycarbonyl group, an ethoxycarbonyl group, a 2,2-difluoroethoxycarbonyl group, a 2,2,2-trifluoroethoxycarbonyl group, a 3,3,3-trifluoropropyloxycarbonyl group, a cyclopropyloxycarbonyl group, an aminocarbonyl group, a methylaminocarbonyl group, an ethylaminocarbonyl group, a (methoxymethyl)aminocarbonyl group, a (2-methoxyethyl)aminocarbonyl group, a (cyanomethyl)aminocarbonyl group, a (2-cyanoethyl)aminocarbonyl group, a dimethylaminocarbonyl group, an ethylmethylaminocarbonyl group, a diethylaminocarbonyl group, a (methoxymethyl)methylaminocarbonyl group, a (2-methoxyethyl)methylaminocarbonyl group, a (cyanomethyl)methylaminocarbonyl group, a (2-cyanoethyl)methylaminocarbonyl group, a 2,2-difluoroethylaminocarbonyl group, a 2,2,2-trifluoroethylaminocarbonyl group, a cyclopropylaminocarbonyl group, a (cyclopropyl)methylaminocarbonyl group, a pyrrolidinylcarbonyl group or a piperidinylcarbonyl group, and further preferably an acetyl group, a methoxyacetyl group, a cyanoacetyl group, a difluoroacetyl group, a trifluoroacetyl group, a methoxycarbonyl group, an ethoxycarbonyl group, an aminocarbonyl group, a dimethylaminocarbonyl group, an ethylmethylaminocarbonyl group or a diethylaminocarbonyl group.

(327) Rx1 of the “Rx1C(═O)O—” in R5 of Formula (1) is the same as defined hereinabove. The Rx1 is preferably a C1-C6 alkyl group optionally substituted with substituent(s) B, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C3-C8 cycloalkoxy group or RaRbN— (wherein Ra and Rb are the same as defined hereinabove), further preferably a C1-C6 alkyl group optionally substituted with substituent(s) B, a C1-C6 haloalkyl group, a C1-C6 alkoxy group or RaRbN— (wherein Ra and Rb are the same as defined hereinabove), and particularly preferably a C1-C6 alkyl group optionally substituted with substituent(s) B. The “Rx1C(═O)O—” is preferably an acetyloxy group, a methoxyacetyloxy group, a cyanoacetyloxy group, a propionyloxy group, a difluoroacetyloxy group; a trifluoroacetyloxy group, a cyclopropancarbonyloxy group, a methoxycarbonyloxy group, an ethoxycarbonyloxy group, a 2,2-difluoroethoxycarbonyloxy group, a 2,2,2-trifluoroethoxycarbonyloxy group, a 3,3,3-trifluoropropyloxycarbonyloxy group, a cyclopropyloxycarbonyloxy group, an aminocarbonyloxy group, a methylaminocarbonyloxy group, an ethylaminocarbonyloxy group, a (methoxymethyl)aminocarbonyloxy group, a (2-methoxyethyl)aminocarbonyloxy group, a (cyanomethyl)aminocarbonyloxy group, a (2-cyanoethyl)aminocarbonyloxy group, a dimethylaminocarbonyloxy group, an ethylmethylaminocarbonyloxy group, a diethylaminocarbonyloxy group, a (methoxy-methyl)methylaminocarbonyloxy group, a (2-methoxyethyl)methylaminocarbonyloxy group, a (cyanomethyl)methylaminocarbonyloxy group, a (2-cyanoethyl)methylamino-carbonyloxy group, a 2,2-difluoroethylaminocarbonyloxy group, a 2,2,2-trifluoroethylaminocarbonyloxy group, a cyclopropylaminocarbonyloxy group, a (cyclopropyl)methylaminocarbonyloxy group, a pyrrolidinylcarbonyloxy group or a piperidinylcarbonyloxy group, further preferably an acetyloxy group, a methoxyacetyloxy group, a cyanoacetyloxy group, a difluoroacetyloxy group, a trifluoroacetyloxy group, a methoxycarbonyloxy group, an ethoxycarbonyloxy group, an aminocarbonyloxy group, a dimethylaminocarbonyloxy group, an ethylmethylaminocarbonyloxy group or a diethylaminocarbonyloxy group, and particularly preferably an acetyloxy group.

(328) Each term of the “Rx2C(═O)N(Rx3)-” (wherein Rx2 represents a hydrogen atom, a C1-C6 alkyl group optionally substituted with substituent(s) B, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C3-C8 cycloalkoxy group or RaRbN— (wherein Ra and Rb are the same as defined hereinabove), Rx3 represents a hydrogen atom, a C1-C6 alkyl group optionally substituted with substituent(s) B, a C1-C6 haloalkyl group or a C3-C8 cycloalkyl group.) in R5 of Formula (1) is the same as defined hereinabove. Incidentally, with regard to the “C1-C6 alkyl group optionally substituted with substituent(s) B”, when it has the substituent(s) B, the C1-C6 alkyl group is optionally substituted with the substituent(s) B in place of hydrogen atom(s). The Rx2 is preferably a hydrogen atom, a methyl group, a methoxymethyl group, a cyanomethyl group, an ethyl group, a difluoromethyl group, a trifluoromethyl group, a cyclopropyl group, a methoxy group, an ethoxy group, a 2,2-difluoroethoxy, a 2,2,2-trifluoroethoxy group, a cyclopropyloxy group, an amino group, a methylamino group, an ethylamino group, a (methoxymethyl)amino group, a (2-methoxyethyl)amino group, a (cyanomethyl)amino group, a (2-cyanoethyl)amino group, a dimethylamino group, an ethylmethylamino group, a diethylamino group, a (methoxymethyl)methylamino group, a (2-methoxyethyl)methylamino group, a (cyanomethyl)methylamino group, a (2-cyanoethyl)methylamino group, a 2,2-difluoroethylamino group, a 2,2,2-trifluoroethylamino group, a cyclopropylamino group, a (cyclopropyl)methylamino group, a pyrrolidinyl group or a piperidinyl group, further preferably a hydrogen atom, a methyl group, a methoxymethyl group, a cyanomethyl group, a difluoromethyl group, a trifluoromethyl group, a methoxy group, an ethoxy group, an amino group, a dimethylamino group, an ethylmethylamino group or a diethylamino group. Also, Rx3 is preferably a hydrogen atom, a methyl group, a methoxymethyl group, an ethoxymethyl group, a cyanomethyl group, an ethyl group, a 2-methoxyethyl group, a 2-ethoxyethyl group, a 2-cyanoethyl group, a propyl group, a 2,2-difluoroethyl group, a 2,2,2-trifluoroethyl group or a cyclopropyl group, and further preferably a hydrogen atom, a methyl group, a methoxymethyl group, a cyanomethyl group, an ethyl group, a 2-methoxyethyl group, a 2,2-difluoroethyl group or a 2,2,2-trifluoroethyl group.

(329) Each term of the “Rx4Rx5C═N—O—” (wherein Rx4 and Rx5 each independently represent a hydrogen atom, a C1-C6 alkyl group optionally substituted with substituent(s) B, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C3-C8 cycloalkoxy group or RaRbN— (wherein Ra and Rb are the same as defined hereinabove)) in R5 of Formula (1) is the same as defined hereinabove. Incidentally, with regard to the “C1-C6 alkyl group optionally substituted with substituent(s) B”, when it has the substituent(s) B, the C1-C6 alkyl group is optionally substituted with the substituent(s) B in place of hydrogen atom(s).

(330) Rx4 and Rx5 are each preferably a methyl group, an ethyl group, a propyl group, an isopropyl group, a trifluoromethyl group, a 2,2,2-trifluoroethyl group, a cyclopropyl group, a cyclopentyl group, a cyclohexyl group, a methoxy group, an ethoxy group, isopropyloxy group, a difluoromethoxy group, a trifluoromethoxy group, a 2,2-difluoroethoxy group, a 2,2,2-trifluoroethoxy group, a cyclopropyloxy group, a cyclobutyloxy group, a cyclopentyloxy group, an amino group, a methylamino group, an ethylamino group, a (methoxymethyl)amino group, a (2-methoxyethyl)amino group, a (cyanomethyl)amino group, a (2-cyanoethyl)amino group, a dimethylamino group, an ethylmethylamino group, a diethylamino group, a (methoxymethyl)methylamino group, a (2-methoxyethyl)methylamino group, a (cyanomethyl)methylamino group, a (2-cyanoethyl)methylamino group, a 2,2-difluoroethylamino group, a 2,2,2-trifluoroethylamino group, a cyclopropylamino group, a (cyclopropyl)methylamino group, a pyrrolidinyl group or a piperidinyl group, and further preferably a methyl group, an ethyl group, a trifluoromethyl group, a 2,2,2-trifluoroethyl group, a methoxy group, an ethoxy group, a 2,2,2-trifluoroethoxy group, a dimethylamino group, an ethylmethylamino group or a diethylamino group.

(331) The “3 to 6 membered ring group containing 1 to 2 oxygen atoms in R5 of Formula (1) is the same as defined hereinabove, preferably an oxolanyl group, an oxanyl group, a 1,3-dioxolanyl group or a 1,3-dioxanyl group, and further preferably a 1,3-dioxolanyl group or a 1,3-dioxanyl group.

(332) In the following, Y in Formula (1) will be described in detail.

(333) A) When Y is a phenyl group, Y represents a partial structure represented by Formula (k)

(334) ##STR00090##
(wherein R4 and R5 is the same as defined hereinabove and “ma” represents an integer of 0 to 4).

(335) “ma” in Formula (k) represents an integer of 0 to 4.

(336) When “ma” of Formula (k) is 2 or more, the two or more substituents R5 are independent of one another and may be optionally selected to be the same as or different from one another.

(337) In the present specification, when Y is a phenyl group, the ortho position indicates the position in the phenyl group at which there is the substituent R4 as illustrated in Formula (k).

(338) The phenyl group in which the substituent R4 is positioned at the ortho position constitutes the characteristics of the present invention.

(339) Preferred combination of the substituents of Formula (k) is a 2-R4-phenyl group, a 2-R4-6-R5-phenyl group, a 2-R4-4-R5-phenyl group, a 2-R4-4-R5-6-R5-phenyl group, a 2-R4-3-R5-phenyl group or a 2-R4-3-R5-4-R5-6-R5-phenyl group, and more preferred combination of the substituents is a 2-R4-phenyl group, a 2-R4-6-R5-phenyl group, a 2-R4-4-R5-phenyl group, a 2-R4-4-R5-6-R5-phenyl group or a 2-R4-3-R5-4-R5-6-R5-phenyl group. Here, for example, the “2-R4-6-R5-phenyl group” indicates a di-substituted phenyl group having the substituent R4 at the 2-position and the substituent R5 at the 6-position, and the same applies hereinafter.

(340) B) When Y is a pyridyl group, a pyridazinyl group, a pyrimidinyl group, a pyrazinyl group, a triazinyl group or tetrazinyl group, Y represents a partial structure represented by Formula (L)

(341) ##STR00091##
(wherein R4, R5 are the same as defined hereinabove and “mb” represents an integer of 0 to 3).

(342) G30, G31, G32 and G33 in Formula (L) are each independent and represent a carbon atom or a nitrogen atom. With the proviso that at least one among G30, G31, G32 and G33 is a nitrogen atom. Preferred G30, G31, G32 and G33 are that any one of G30, G31, G32 and G33 is a nitrogen atom. That is, it is a pyridyl group.

(343) “mb” in Formula (L) represents an integer of 0 to 3.

(344) When “mb” of Formula (L) is 2 or more, the two or more substituents R5 are independent of one another and may be optionally selected to be the same as or different from one another.

(345) In the present specification, when Y is a pyridyl group, a pyridazinyl group, a pyrimidinyl group, a pyrazinyl group, a triazinyl group or a tetrazinyl group, the ortho position indicates the position in the 6-membered ring at which there is the substituent R4 as illustrated in Formula (L).

(346) Specific examples of the partial structures represented by Formula (L) are illustrated below.

(347) ##STR00092##

(348) The pyridyl group, the pyridazinyl group, the pyrimidinyl group, the pyrazinyl group, the triazinyl group or the tetrazinyl group in which the substituent R4 is positioned at the ortho position constitute the characteristics of the present invention.

(349) Preferred specific examples of Formula (L) are a 3-R4-pyridin-2-yl group, a 3-R4-5-R5-pyridin-2-yl group, a 2-R4-pyridin-3-yl group, a 2-R4-4-R5-pyridin-3-yl group, a 2-R4-6-R5-pyridin-3-yl group, a 2-R4-4-R5-6-R5-pyridin-3-yl group, a 4-R4-pyridin-3-yl group, a 4-R4-2-R5-pyridin-3-yl group, a 4-R4-6-R5-pyridin-3-yl group, a 4-R4-2-R5-6-R5-pyridin-3-yl group, a 3-R4-pyridin-4-yl group or a 3-R4-5-R5-pyridin-4-yl group.

(350) C) When Y is a thienyl group, a thiazolyl group, an isothiazolyl group or a thiadiazolyl group, Y represents a partial structure represented by

(351) ##STR00093##

(352) ##STR00094##
or

(353) ##STR00095##
(wherein R4 and R5 are the same as defined hereinabove and “mc” represents an integer of 0 to 2).

(354) G34 and G35 in Formula (m-1), Formula (m-2) and Formula (m-3) are each independent and represent a carbon atom or a nitrogen atom.

(355) “mc” in Formula (m-1), Formula (m-2) and Formula (m-3) represents an integer of 0 to 2.

(356) When “mc” in Formula (m-1), Formula (m-2) and Formula (m-3) is 2, the two substituents R5 are independent of one another and may be optionally selected to be the same as or different from one another.

(357) In the present specification, when Y is a thienyl group, a thiazolyl group, an isothiazolyl group or a thiadiazolyl group, the ortho position indicates the position in the 5-membered ring at which there is the subsistent R4 as illustrated in Formula (m-1), Formula (m-2) and Formula (m-3).

(358) Specific examples of the partial structures represented by Formula (m-1) are illustrated below.

(359) ##STR00096##

(360) Specific examples of the partial structures represented by Formula (m-2) are illustrated below.

(361) ##STR00097##

(362) Specific examples of the partial structures represented by Formula (m-3) are illustrated below.

(363) ##STR00098##

(364) The thienyl group, the thiazolyl group, the isothiazolyl group or the thiadiazolyl group in which the substituent R4 is positioned at the ortho position constitute the characteristics of the present invention.

(365) X in Formula (1) represents an oxygen atom or a sulfur atom. Preferable X is an oxygen atom.

(366) A bond containing the broken line in Formula (1) represents the portion represented by

(367) [Chem. 80]

(368) The bond containing the broken line in Formula (1) represents a double bond or a single bond.

(369) When the bond containing the a broken line in Formula (1) is a double bond, the compound represented by Formula (1a)

(370) ##STR00099##
(wherein R1, R2, Het, X and Y are the same as defined in Formula (1)) or a salt thereof is represented.

(371) When the bond containing the broken line in Formula (1) is a single bond, the compound represented by Formula (1b)

(372) ##STR00100##
(wherein R1, R2, Het, X and Y are the same as defined in Formula (1).) or a salt thereof is represented.

(373) When R2 in Formula (1b) is a substituent other than hydrogen, the compound is either one of the R-isomer or the S-isomer, or a mixture of the R-isomer and the S-isomer with an optional ratio.

(374) The “substituent(s) A” in Formula (1) represents at least one kind selected from the group consisting of a hydroxyl group, a cyano group, a C3-C8 cycloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C3-C8 cycloalkoxy group, RaRbN— (wherein Ra and Rb are the same as defined hereinabove.) and Rc-L- (wherein Rc and L are the same as defined hereinabove).

(375) Above all, the substituent(s) A is preferably a cyano group, a C1-C6 alkoxy group or Rc-L- (wherein Rc and L are the same as defined hereinabove), and

(376) particularly preferably a cyano group or a C1-C6 alkoxy group.

(377) Preferred specific examples of the substituent(s) A may include a hydroxyl group; a cyano group;

(378) a cyclopropyl group, a cyclobutyl group, a cyclopentyl group and a cyclohexyl group as the C3-C8 cycloalkyl group;

(379) a methoxy group, an ethoxy group, a propyloxy group and an isopropyloxy group as the C1-C6 alkoxy group;

(380) a difluoromethoxy group, a trifluoromethoxy group, a 2,2-difluoroethoxy group, a 2,2,2-trifluoroethoxy group, a 3,3-difluoropropyloxy group and a 3,3,3-trifluoro-propyloxy group as the C1-C6 haloalkoxy group;

(381) a cyclopropyloxy group, a cyclobutoxy group, a cyclopentyloxy group and a cyclohexyloxy group as the C3-C8 cycloalkoxy group;

(382) an amino group, a methylamino group, an ethylamino group, a (methoxymethyl)amino group, a (2-methoxyethyl)amino group, a (cyanomethyl)amino group, a (2-cyanoethyl)-amino group, a dimethylamino group, an ethylmethylamino group, a diethylamino group, a (methoxymethyl)methylamino group, a (2-methoxyethyl)methylamino group, a (cyanomethyl)methylamino group, a (2-cyanoethyl)methylamino group, a 2,2-difluoroethylamino group, a 2,2,2-trifluoroethylamino group, a cyclopropylamino group, a (cyclopropyl)methylamino group, a pyrrolidinyl group and a piperidinyl group as the RaRbN— (wherein Ra and Rb are the same as defined hereinabove);
and a methylthio group, a methanesulfinyl group, a methanesulfonyl group, a trifluoromethylthio group, a trifluoromethanesulfinyl group and a trifluoromethanesulfonyl group as the Rc-L- (wherein Rc and L are the same as defined hereinabove).

(383) More preferred specific examples of the substituent(s) A may include a hydroxyl group; a cyano group;

(384) a cyclopropyl group and a cyclobutyl group as the C3-C8 cycloalkyl group,

(385) a methoxy group and an ethoxy group as the C1-C6 alkoxy group,

(386) a difluoromethoxy group, a trifluoromethoxy group, a 2,2-difluoroethoxy group and a 2,2,2-trifluoroethoxy group as the C1-C6 haloalkoxy group,

(387) a cyclopropyloxy group and a cyclobutoxy group as the C3-C8 cycloalkoxy group,

(388) a dimethylamino group, an ethylmethylamino group and a diethylamino group as the RaRbN— (wherein Ra and Rb are the same as defined hereinabove),

(389) and a methylthio group, a methanesulfinyl group and a methanesulfonyl group as the Rc-L- (wherein Rc and L are the same as defined hereinabove).

(390) The “substituent(s) B” in Formula (1) represents at least one kind selected from the group consisting of a cyano group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group and a C3-C8 cycloalkoxy group.

(391) Above all, the substituent(s) B is preferably a cyano group or a C1-C6 alkoxy group.

(392) Preferred specific examples of the substituent(s) B may include a cyano group; a methoxy group, an ethoxy group, a propyloxy group and an isopropyloxy group as the C1-C6 alkoxy group;

(393) a difluoromethoxy group, a trifluoromethoxy group, a 2,2-difluoroethoxy group, a 2,2,2-trifluoroethoxy group, a 3,3-difluoropropyloxy group and a 3,3,3-trifluoro-propyloxy group as the C1-C6 haloalkoxy group;

(394) and a cyclopropyloxy group, a cyclobutoxy group, a cyclopentyloxy group and a cyclohexyloxy group as the C3-C8 cycloalkoxy group.

(395) More preferred specific examples of the substituent(s) B may include a cyano group;

(396) a methoxy group and an ethoxy group as the C1-C6 alkoxy group;

(397) a difluoromethoxy group, a trifluoromethoxy group, a 2,2-difluoroethoxy group and a 2,2,2-trifluoroethoxy group as the C1-C6 haloalkoxy group;

(398) and a cyclopropyloxy group and a cyclobutoxy group as the C3-C8 cycloalkoxy group.

(399) The “substituent(s) C” in Formula (1) represents at least one kind selected from the group consisting of a hydroxyl group, a cyano group, a C3-C8 cycloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C3-C8 cycloalkoxy group, a C2-C6 alkoxyalkoxy group, RaRbN— (wherein Ra and Rb are the same as defined hereinabove), Rc-L- (wherein Rc and L are the same as defined hereinabove), Rx1C(═O)— (wherein Rx1 is the same as defined hereinabove.) and a 3 to 6-membered ring group containing 1 to 2 oxygen atoms;

(400) above all, the substituent(s) C is preferably a cyano group, a C3-C8 cycloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C2-C6 alkoxyalkoxy group, Rc-L- (wherein Rc and L are the same as defined hereinabove), Rx1C(═O)— (wherein Rx1 is the same as defined hereinabove.) or a 3 to 6-membered ring group containing 1 to 2 oxygen atoms, and

(401) particularly preferably a cyano group, a C1-C6 alkoxy group or Rc-L- (wherein Rc and L are the same as defined hereinabove).

(402) Preferred specific examples of the substituent(s) C may include a hydroxyl group; a cyano group;

(403) a cyclopropyl group, a cyclobutyl group, a cyclopentyl group and a cyclohexyl group as the C3-C8 cycloalkyl group;

(404) a methoxy group, an ethoxy group, a propyloxy group, an isopropyloxy group, a butoxy group, an isobutoxy group and a t-butoxy group as the C1-C6 alkoxy group;

(405) a difluoromethoxy group, a trifluoromethoxy group, a 2,2-difluoroethoxy group, a 2,2,2-trifluoroethoxy group, a 3,3-difluoropropyloxy group and a 3,3,3-trifluoro-propyloxy group as the C1-C6 haloalkoxy group;

(406) a cyclopropyloxy group, a cyclobutoxy group, a cyclopentyloxy group and a cyclohexyloxy group as the C3-C8 cycloalkoxy group;

(407) a methoxymethoxy group, an ethoxymethoxy group, a methoxyethoxy group, an ethoxyethoxy group and a methoxypropyloxy group as the C2-C6 alkoxyalkoxy group;

(408) an amino group, a methylamino group, an ethylamino group, a (methoxymethyl)amino group, a (2-methoxyethyl)amino group, a (cyanomethyl)amino group, a (2-cyanoethyl)-amino group, a dimethylamino group, an ethylmethylamino group, a diethylamino group, a (methoxymethyl)methylamino group, a (2-methoxyethyl)methylamino group, a (cyanomethyl)methylamino group, a (2-cyanoethyl)methylamino group, a 2,2-difluoroethylamino group, a 2,2,2-trifluoroethylamino group, a cyclopropylamino group, a (cyclopropyl)methylamino group, a pyrrolidinyl group and a piperidinyl group as the RaRbN— (wherein Ra and Rb are the same as defined hereinabove);
a methylthio group, a methanesulfinyl group, a methanesulfonyl group, a trifluoromethylthio group, a trifluoromethanesulfinyl group and a trifluoromethanesulfonyl group as the Rc-L- (wherein Rc and L are the same as defined hereinabove);
a formyl group, an acetyl group, a methoxyacetyl group, a cyanoacetyl group, a propionyl group, a difluoroacetyl group, a trifluoroacetyl group, a cyclopropancarbonyl group, a methoxycarbonyl group, an ethoxycarbonyl group, a 2,2-difluoroethoxycarbonyl group, a 2,2,2-trifluoroethoxycarbonyl group, a 3,3,3-trifluoropropyloxycarbonyl group, a cyclopropyloxycarbonyl group, an aminocarbonyl group, a methylaminocarbonyl group, an ethylaminocarbonyl group, a (methoxymethyl)-aminocarbonyl group, a (2-methoxyethyl)aminocarbonyl group, a (cyanomethyl)-aminocarbonyl group, a (2-cyanoethyl)aminocarbonyl group, a dimethylaminocarbonyl group, an ethylmethylaminocarbonyl group, a diethylaminocarbonyl group, a (methoxymethyl)methylaminocarbonyl group, a (2-methoxyethyl)methylaminocarbonyl group, a (cyanomethyl)methylaminocarbonyl group, a (2-cyanoethyl)methylaminocarbonyl group, a 2,2-difluoroethylaminocarbonyl group, a 2,2,2-trifluoroethylaminocarbonyl group, a cyclopropylaminocarbonyl group, a (cyclopropyl)methylaminocarbonyl group, a pyrrolidinylcarbonyl group and a piperidinylcarbonyl group as the Rx1C(═O)— (wherein Rx1 is the same as defined hereinabove);
and an oxolanyl group, an oxanyl group, a 1,3-dioxolanyl group and a 1,3-dioxanyl group as the 3 to 6 membered ring group containing 1 to 2 oxygen atoms.

(409) More preferred specific examples of the substituent(s) C may include a hydroxyl group; a cyano group;

(410) a cyclopropyl group and a cyclobutyl group as the C3-C8 cycloalkyl group;

(411) a methoxy group and an ethoxy group as the C1-C6 alkoxy group;

(412) a difluoromethoxy group, a trifluoromethoxy group, a 2,2-difluoroethoxy group and a 2,2,2-trifluoroethoxy group as the C1-C6 haloalkoxy group;

(413) a cyclopropyloxy group and a cyclobutoxy group as the C3-C8 cycloalkoxy group;

(414) a methoxymethoxy group, an ethoxymethoxy group, a methoxyethoxy group and an ethoxyethoxy group as the C2-C6 alkoxyalkoxy group;

(415) a dimethylamino group, an ethylmethylamino group and a diethylamino group as the RaRbN— (wherein Ra and Rb are the same as defined hereinabove);

(416) a methylthio group, a methanesulfinyl group and a methanesulfonyl group as the Rc-L- (wherein Rc and L are the same as defined hereinabove);

(417) a formyl group, an acetyl group, a methoxyacetyl group, a cyanoacetyl group, a difluoroacetyl group, a trifluoroacetyl group, a methoxycarbonyl group, an ethoxycarbonyl group, an aminocarbonyl group, a dimethylaminocarbonyl group, an ethylmethylaminocarbonyl group and a diethylaminocarbonyl group as the Rx1C(═O)— (wherein Rx1 is the same as defined hereinabove);
and a 1,3-dioxolanyl group and a 1,3-dioxanyl group as the 3 to 6-membered ring group containing 1 to 2 oxygen atoms.

(418) The “substituent(s) D” in Formula (1) represents at least one kind selected from the group consisting of a hydroxyl group, a cyano group, a nitro group, a halogen atom, a C1-C6 alkyl group optionally substituted with substituent(s) B, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group, a C1-C6 alkoxy group, C1-C6 haloalkoxy group and a C3-C8 cycloalkoxy group.

(419) Above all, the substituent(s) D is preferably a cyano group, a halogen atom, a C1-C6 alkyl group optionally substituted with substituent(s) B, a C1-C6 haloalkyl group, a C1-C6 alkoxy group or C1-C6 haloalkoxy group.

(420) Preferred specific examples of the substituent(s) D may include a hydroxyl group; a cyano group; a nitro group;

(421) a fluorine atom, a chlorine atom, a bromine atom and an iodine atom as the halogen atom;

(422) a methyl group, a methoxymethyl group, an ethoxymethyl group, a cyanomethyl group, an ethyl group, a 2-methoxyethyl group, a 2-ethoxyethyl group, a 2-cyanoethyl group, a propyl group, an isopropyl group, a butyl group and an isobutyl group as the C1-C6 alkyl group optionally substituted with substituent(s) B;
a difluoromethyl group, a trifluoromethyl group, a 2,2-difluoroethyl group, a 2,2,2-trifluoroethyl group, a 3,3-difluoropropyl group and a 3,3,3-trifluoropropyl group as the C1-C6 haloalkyl group;
a cyclopropyl group, a cyclobutyl group, a cyclopentyl group and a cyclohexyl group as the C3-C8 cycloalkyl group;
a methoxy group, an ethoxy group, a propyloxy group, an isopropyloxy group, a butoxy group, an isobutoxy group and a t-butoxy group as the C1-C6 alkoxy group;
a difluoromethoxy group, a trifluoromethoxy group, a 2,2-difluoroethoxy group, a 2,2,2-trifluoroethoxy group, a 3,3-difluoropropyloxy group and a 3,3,3-trifluoropropyloxy group as the C1-C6 haloalkoxy group;
and a cyclopropyloxy group, a cyclobutoxy group, a cyclopentyloxy group and a cyclohexyloxy group as the C3-C8 cycloalkoxy group.

(423) More preferred specific examples of the substituent(s) D may include a hydroxyl group; a cyano group; a nitro group;

(424) a fluorine atom, a chlorine atom and a bromine atom as the halogen atom;

(425) a methyl group, a methoxymethyl group, an ethoxymethyl group, a cyanomethyl group, an ethyl group, a 2-methoxyethyl group, a 2-ethoxyethyl group and a 2-cyanoethyl group as the C1-C6 alkyl group optionally substituted with substituent(s) B; a difluoromethyl group, a trifluoromethyl group, a 2,2-difluoroethyl group and a 2,2,2-trifluoroethyl group as the C1-C6 haloalkyl group;
a cyclopropyl group and a cyclobutyl group as the C3-C8 cycloalkyl group;
a methoxy group, an ethoxy group, a propyloxy group and an isopropyloxy group as the C1-C6 alkoxy group;
a difluoromethoxy group, a trifluoromethoxy group, a 2,2-difluoroethoxy group and a 2,2,2-trifluoroethoxy group as the C1-C6 haloalkoxy group;
and a cyclopropyloxy group and a cyclobutoxy group as the C3-C8 cycloalkoxy group.

(426) The compound represented by Formula (1) may have one or two axial chirality. A ratio of the isomers at this time is a single isomer or a mixture of isomers with an optional ratio, and is not particularly limited.

(427) The compound represented by Formula (1) may contain an asymmetric atom. A ratio of the isomers at this time is a single isomer or a mixture of isomers with an optional ratio, and is not particularly limited.

(428) The compound represented by Formula (1) may contain geometric isomers. A ratio of the isomers at this time is a single isomer or a mixture of isomers with an optional ratio, and is not particularly limited.

(429) The compound represented by Formula (1) may form a salt. There may be exemplified salts formed with acids such as hydrochloric acid, sulfuric acid, acetic acid, fumaric acid and maleic acid, and salts formed with metals such as sodium, potassium and calcium, but these salts are not particularly limited as long as they are usable as agricultural and horticultural fungicides.

(430) All the scope of the compounds obtainable by optionally combining the preferable scope in R1, R2, Het, R3, Y, R4, R5, X, the bond containing the broken line, the substituent(s) A, the substituent(s) B, the substituent(s) C and the substituent(s) D explained hereinabove are also to be described herein as a scope of Formula (1) of the present invention or its production intermediate compounds.

(431) Next, specific compounds of the present invention are shown by combinations of the structural formulae P-1 to P-77 illustrated in Table 1 (wherein X in Table 1 is an oxygen atom or a sulfur atom, a bond containing a broken line represents a double bond or a single bond), the structural formulae (Y-1 to Y-408) of Y illustrated in Table 2 (wherein Y is the same as defined hereinabove), and the structural formulae (Het-1 to Het-2880) of Het illustrated in Table 3 (wherein Het is the same as defined hereinabove). Those compounds are only illustrative and the scope of the present invention is not limited to these compounds.

(432) TABLE-US-00001 TABLE 1 01 P-1 02 P-2 03 P-3 04 P-4 05 P-5 06 P-6 07 P-7 08 P-8 09 P-9 0 P-10 P-11 P-12 P-13 P-14 P-15 P-16 P-17 P-18 P-19 0 P-20 P-21 P-22 P-23 P-24 P-25 P-26 P-27 P-28 P-29 0 P-30 P-31 P-32 P-33 P-34 P-35 P-36 P-37 P-38 P-39 0 P-40 P-41 P-42 P-43 P-44 P-45 P-46 P-47 P-48 P-49 0 P-50 P-51 P-52 P-53 P-54 P-55 P-56 P-57 P-58 P-59 0 P-60 P-61 P-62 P-63 P-64 P-65 P-66 P-67 P-68 P-69 0 P-70 P-71 P-72 P-73 P-74 P-75 P-76 P-77

(433) TABLE-US-00002 TABLE 2 Y-1 Y-2 0 Y-3 Y-4 Y-5 Y-6 Y-7 Y-8 Y-9 Y-10 Y-11 Y-12 0 Y-13 Y-14 Y-15 Y-16 Y-17 Y-18 Y-19 Y-20 Y-21 Y-22 00 Y-23 01 Y-24 02 Y-25 03 Y-26 04 Y-27 05 Y-28 06 Y-29 07 Y-30 08 Y-31 09 Y-32 0 Y-33 Y-34 Y-35 Y-36 Y-37 Y-38 Y-39 Y-40 Y-41 Y-42 0 Y-43 Y-44 Y-45 Y-46 Y-47 Y-48 Y-49 Y-50 Y-51 Y-52 0 Y-53 Y-54 Y-55 Y-56 Y-57 Y-58 Y-59 Y-60 Y-61 Y-62 0 Y-63 Y-64 Y-65 Y-66 Y-67 Y-68 Y-69 Y-70 Y-71 Y-72 0 Y-73 Y-74 Y-75 Y-76 Y-77 Y-78 Y-79 Y-80 Y-81 Y-82 0 Y-83 Y-84 Y-85 Y-86 Y-87 Y-88 Y-89 Y-90 Y-91 Y-92 0 Y-93 Y-94 Y-95 Y-96 Y-97 Y-98 Y-99 Y-100 Y-101 Y-102 0 Y-103 Y-104 Y-105 Y-106 Y-107 Y-108 Y-109 Y-110 Y-111 Y-112 0 Y-113 Y-114 Y-115 Y-116 Y-117 Y-118 Y-119 Y-120 Y-121 Y-122 00 Y-123 01 Y-124 02 Y-125 03 Y-126 04 Y-127 05 Y-128 06 Y-129 07 Y-130 08 Y-131 09 Y-132 0 Y-133 Y-134 Y-135 Y-136 Y-137 Y-138 Y-139 Y-140 Y-141 Y-142 0 Y-143 Y-144 Y-145 Y-146 Y-147 Y-148 Y-149 Y-150 Y-151 Y-152 0 Y-153 Y-154 Y-155 Y-156 Y-157 Y-158 Y-159 Y-160 Y-161 Y-162 0 Y-163 Y-164 Y-165 Y-166 Y-167 Y-168 Y-169 Y-170 Y-171 Y-172 0 Y-173 Y-174 Y-175 Y-176 Y-177 Y-178 Y-179 Y-180 Y-181 Y-182 0 Y-183 Y-184 Y-185 Y-186 Y-187 Y-188 Y-189 Y-190 Y-191 Y-192 0 Y-193 Y-194 Y-195 Y-196 Y-197 Y-198 Y-199 Y-200 Y-201 Y-202 0 Y-203 Y-204 Y-205 Y-206 Y-207 Y-208 Y-209 Y-210 Y-211 Y-212 0 Y-213 Y-214 Y-215 Y-216 Y-217 Y-218 Y-219 Y-220 Y-221 Y-222 00 Y-223 01 Y-224 02 Y-225 03 Y-226 04 Y-227 05 Y-228 06 Y-229 07 Y-230 08 Y-231 09 Y-232 0 Y-233 Y-234 Y-235 Y-236 Y-237 Y-238 Y-239 Y-240 Y-241 Y-242 0 Y-243 Y-244 Y-245 Y-246 Y-247 Y-248 Y-249 Y-250 Y-251 Y-252 0 Y-253 Y-254 Y-255 Y-256 Y-257 Y-258 Y-259 Y-260 Y-261 Y-262 0 Y-263 Y-264 Y-265 Y-266 Y-267 Y-268 Y-269 Y-270 Y-271 Y-272 0 Y-273 Y-274 Y-275 Y-276 Y-277 Y-278 Y-279 Y-280 Y-281 Y-282 0 Y-283 Y-284 Y-285 Y-286 Y-287 Y-288 Y-289 Y-290 Y-291 Y-292 0 Y-293 Y-294 Y-295 Y-296 Y-297 Y-298 Y-299 Y-300 Y-301 Y-302 0 Y-303 Y-304 Y-305 Y-306 Y-307 Y-308 Y-309 Y-310 Y-311 Y-312 0 Y-313 Y-314 Y-315 Y-316 Y-317 Y-318 Y-319 Y-320 Y-321 Y-322 00 Y-323 01 Y-324 02 Y-325 03 Y-326 04 Y-327 05 Y-328 06 Y-329 07 Y-330 08 Y-331 09 Y-332 0 Y-333 Y-334 Y-335 Y-336 Y-337 Y-338 Y-339 Y-340 Y-341 Y-342 0 Y-343 Y-344 Y-345 Y-346 Y-347 Y-348 Y-349 Y-350 Y-351 Y-352 0 Y-353 Y-354 Y-355 Y-356 Y-357 Y-358 Y-359 Y-360 Y-361 Y-362 0 Y-363 Y-364 Y-365 Y-366 Y-367 Y-368 Y-369 Y-370 Y-371 Y-372 0 Y-373 Y-374 Y-375 Y-376 Y-377 Y-378 Y-379 Y-380 Y-381 Y-382 0 Y-383 Y-384 Y-385 Y-386 Y-387 Y-388 Y-389 Y-390 Y-391 Y-392 0 Y-393 Y-394 Y-395 Y-396 Y-397 Y-398 Y-399 Y-400 Y-401 Y-402 0 Y-403 Y-404 Y-405 Y-406 Y-407 Y-408

(434) TABLE-US-00003 TABLE 3 Het-1 Het-2 Het-3 Het-4 0 Het-5 Het-6 Het-7 Het-8 Het-9 Het-10 Het-11 Het-12 Het-13 Het-14 00 Het-15 01 Het-16 02 Het-17 03 Het-18 04 Het-19 05 Het-20 06 Het-21 07 Het-22 08 Het-23 09 Het-24 0 Het-25 Het-26 Het-27 Het-28 Het-29 Het-30 Het-31 Het-32 Het-33 Het-34 0 Het-35 Het-36 Het-37 Het-38 Het-39 Het-40 Het-41 Het-42 Het-43 Het-44 0 Het-45 Het-46 Het-47 Het-48 Het-49 Het-50 Het-51 Het-52 Het-53 Het-54 0 Het-55 Het-56 Het-57 Het-58 Het-59 Het-60 Het-61 Het-62 Het-63 Het-64 0 Het-65 Het-66 Het-67 Het-68 Het-69 Het-70 Het-71 Het-72 Het-73 Het-74 0 Het-75 Het-76 Het-77 Het-78 Het-79 Het-80 Het-81 Het-82 Het-83 Het-84 0 Het-85 Het-86 Het-87 Het-88 Het-89 Het-90 Het-91 Het-92 Het-93 Het-94 0 Het-95 Het-96 Het-97 Het-98 Het-99 Het-100 Het-101 Het-102 Het-103 Het-104 0 Het-105 Het-106 Het-107 Het-108 Het-109 Het-110 Het-111 Het-112 Het-113 Het-114 00 Het-115 01 Het-116 02 Het-117 03 Het-118 04 Het-119 05 Het-120 06 Het-121 07 Het-122 08 Het-123 09 Het-124 0 Het-125 Het-126 Het-127 Het-128 Het-129 Het-130 Het-131 Het-132 Het-133 Het-134 0 Het-135 Het-136 Het-137 Het-138 Het-139 Het-140 Het-141 Het-142 Het-143 Het-144 0 Het-145 Het-146 Het-147 Het-148 Het-149 Het-150 Het-151 Het-152 Het-153 Het-154 0 Het-155 Het-156 Het-157 Het-158 Het-159 Het-160 Het-161 Het-162 Het-163 Het-164 0 Het-165 Het-166 Het-167 Het-168 Het-169 Het-170 Het-171 Het-172 Het-173 Het-174 0 Het-175 Het-176 Het-177 Het-178 Het-179 Het-180 Het-181 Het-182 Het-183 Het-184 0 Het-185 Het-186 Het-187 Het-188 Het-189 Het-190 Het-191 Het-192 Het-193 Het-194 0 Het-195 Het-196 Het-197 Het-198 Het-199 Het-200 Het-201 Het-202 Het-203 Het-204 0 Het-205 Het-206 Het-207 Het-208 Het-209 Het-210 Het-211 Het-212 Het-213 Het-214 00 Het-215 01 Het-216 02 Het-217 03 Het-218 04 Het-219 05 Het-220 06 Het-221 07 Het-222 08 Het-223 09 Het-224 0 Het-225 Het-226 Het-227 Het-228 Het-229 Het-230 Het-231 Het-232 Het-233 Het-234 0 Het-235 Het-236 Het-237 Het-238 Het-239 Het-240 Het-241 Het-242 Het-243 Het-244 0 Het-245 Het-246 Het-247 Het-248 Het-249 Het-250 Het-251 Het-252 Het-253 Het-254 0 Het-255 Het-256 Het-257 Het-258 Het-259 Het-260 Het-261 Het-262 Het-263 Het-264 0 Het-265 Het-266 Het-267 Het-268 Het-269 Het-270 Het-271 Het-272 Het-273 Het-274 0 Het-275 Het-276 Het-277 Het-278 Het-279 Het-280 Het-281 Het-282 Het-283 Het-284 0 Het-285 Het-286 Het-287 Het-288 Het-289 Het-290 Het-291 Het-292 Het-293 Het-294 0 Het-295 Het-296 Het-297 Het-298 Het-299 Het-300 Het-301 Het-302 Het-303 Het-304 0 Het-305 Het-306 Het-307 Het-308 Het-309 Het-310 Het-311 Het-312 Het-313 Het-314 00 Het-315 01 Het-316 02 Het-317 03 Het-318 04 Het-319 05 Het-320 06 Het-321 07 Het-322 08 Het-323 09 Het-324 0 Het-325 Het-326 Het-327 Het-328 Het-329 Het-330 Het-331 Het-332 Het-333 Het-334 0 Het-335 Het-336 Het-337 Het-338 Het-339 Het-340 Het-341 Het-342 Het-343 Het-344 0 Het-345 Het-346 Het-347 Het-348 Het-349 Het-350 Het-351 Het-352 Het-353 Het-354 0 Het-355 Het-356 Het-357 Het-358 Het-359 Het-360 Het-361 Het-362 Het-363 Het-364 0 Het-365 Het-366 Het-367 Het-368 Het-369 Het-370 Het-371 Het-372 Het-373 Het-374 0 Het-375 Het-376 Het-377 Het-378 Het-379 Het-380 Het-381 Het-382 Het-383 Het-384 0 Het-385 Het-386 Het-387 Het-388 Het-389 Het-390 Het-391 Het-392 Het-393 Het-394 0 Het-395 Het-396 Het-397 Het-398 Het-399 Het-400 Het-401 Het-402 Het-403 Het-404 0 Het-405 Het-406 Het-407 Het-408 Het-409 Het-410 Het-411 Het-412 Het-413 Het-414 000 Het-415 001 Het-416 002 Het-417 003 Het-418 004 Het-419 005 Het-420 006 Het-421 007 Het-422 008 Het-423 009 Het-424 010 Het-425 011 Het-426 012 Het-427 013 Het-428 014 Het-429 015 Het-430 016 Het-431 017 Het-432 018 Het-433 019 Het-434 020 Het-435 021 Het-436 022 Het-437 023 Het-438 024 Het-439 025 Het-440 026 Het-441 027 Het-442 028 Het-443 029 Het-444 030 Het-445 031 Het-446 032 Het-447 033 Het-448 034 Het-449 035 Het-450 036 Het-451 037 Het-452 038 Het-453 039 Het-454 040 Het-455 041 Het-456 042 Het-457 043 Het-458 044 Het-459 045 Het-460 046 Het-461 047 Het-462 048 Het-463 049 Het-464 050 Het-465 051 Het-466 052 Het-467 053 Het-468 054 Het-469 055 Het-470 056 Het-471 057 Het-472 058 Het-473 059 Het-474 060 Het-475 061 Het-476 062 Het-477 063 Het-478 064 Het-479 065 Het-480 066 Het-481 067 Het-482 068 Het-483 069 Het-484 070 Het-485 071 Het-486 072 Het-487 073 Het-488 074 Het-489 075 Het-490 076 Het-491 077 Het-492 078 Het-493 079 Het-494 080 Het-495 081 Het-496 082 Het-497 083 Het-498 084 Het-499 085 Het-500 086 Het-501 087 Het-502 088 Het-503 089 Het-504 090 Het-505 091 Het-506 092 Het-507 093 Het-508 094 Het-509 095 Het-510 096 Het-511 097 Het-512 098 Het-513 099 Het-514 00 Het-515 01 Het-516 02 Het-517 03 Het-518 04 Het-519 05 Het-520 06 Het-521 07 Het-522 08 Het-523 09 Het-524 0 Het-525 Het-526 Het-527 Het-528 Het-529 Het-530 Het-531 Het-532 Het-533 Het-534 0 Het-535 Het-536 Het-537 Het-538 Het-539 Het-540 Het-541 Het-542 Het-543 Het-544 0 Het-545 Het-546 Het-547 Het-548 Het-549 Het-550 Het-551 Het-552 Het-553 Het-554 0 Het-555 Het-556 Het-557 Het-558 Het-559 Het-560 Het-561 Het-562 Het-563 Het-564 0 Het-565 Het-566 Het-567 Het-568 Het-569 Het-570 Het-571 Het-572 Het-573 Het-574 0 Het-575 Het-576 Het-577 Het-578 Het-579 Het-580 Het-581 Het-582 Het-583 Het-584 0 Het-585 Het-586 Het-587 Het-588 Het-589 Het-590 Het-591 Het-592 Het-593 Het-594 0 Het-595 Het-596 Het-597 Het-598 Het-599 Het-600 Het-601 Het-602 Het-603 Het-604 0 Het-605 Het-606 Het-607 Het-608 Het-609 Het-610 Het-611 Het-612 Het-613 Het-614 00 Het-615 01 Het-616 02 Het-617 03 Het-618 04 Het-619 05 Het-620 06 Het-621 07 Het-622 08 Het-623 09 Het-624 0 Het-625 Het-626 Het-627 Het-628 Het-629 Het-630 Het-631 Het-632 Het-633 Het-634 0 Het-635 Het-636 Het-637 Het-638 Het-639 Het-640 Het-641 Het-642 Het-643 Het-644 0 Het-645 Het-646 Het-647 Het-648 Het-649 Het-650 Het-651 Het-652 Het-653 Het-654 0 Het-655 Het-656 Het-657 Het-658 Het-659 Het-660 Het-661 Het-662 Het-683 Het-664 0 Het-665 Het-666 Het-667 Het-688 Het-669 Het-670 Het-671 Het-672 Het-673 Het-674 0 Het-675 Het-676 Het-677 Het-678 Het-679 Het-680 Het-681 Het-682 Het-683 Het-684 0 Het-685 Het-686 Het-687 Het-688 Het-689 Het-690 Het-691 Het-692 Het-693 Het-694 0 Het-695 Het-696 Het-697 Het-698 Het-699 Het-700 Het-701 Het-702 Het-703 Het-704 0 Het-705 Het-706 Het-707 Het-708 Het-709 Het-710 Het-711 Het-712 Het-713 Het-714 00 Het-715 01 Het-716 02 Het-717 03 Het-718 04 Het-719 05 Het-720 06 Het-721 07 Het-722 08 Het-723 09 Het-724 0 Het-725 Het-726 Het-727 Het-728 Het-729 Het-730 Het-731 Het-732 Het-733 Het-734 0 Het-735 Het-736 Het-737 Het-738 Het-739 Het-740 Het-741 Het-742 Het-743 Het-744 0 Het-745 Het-746 Het-747 Het-748 Het-749 Het-750 Het-751 Het-752 Het-753 Het-754 0 Het-755 Het-756 Het-757 Het-758 Het-759 Het-760 Het-761 Het-762 Het-763 Het-764 0 Het-765 Het-766 Het-767 Het-768 Het-769 Het-770 Het-771 Het-772 Het-773 Het-774 0 Het-775 Het-776 Het-777 Het-778 Het-779 Het-780 Het-781 Het-782 Het-783 Het-784 0 Het-785 Het-786 Het-787 Het-788 Het-789 Het-790 Het-791 Het-792 Het-793 Het-794 0 Het-795 Het-796 Het-797 Het-798 Het-799 Het-800 Het-801 Het-802 Het-803 Het-804 0 Het-805 Het-806 Het-807 Het-808 Het-809 Het-810 Het-811 Het-812 Het-813 Het-814 00 Het-815 01 Het-816 02 Het-817 03 Het-818 04 Het-819 05 Het-820 06 Het-821 07 Het-822 08 Het-823 09 Het-824 0 Het-825 Het-826 Het-827 Het-828 Het-829 Het-830 Het-831 Het-832 Het-833 Het-834 0 Het-835 Het-836 Het-837 Het-838 Het-839 Het-840 Het-841 Het-842 Het-843 Het-844 0 Het-845 Het-846 Het-847 Het-848 Het-849 Het-850 Het-851 Het-852 Het-853 Het-854 0 Het-855 Het-856 Het-857 Het-858 Het-859 Het-860 Het-881 Het-862 Het-863 Het-864 0 Het-865 Het-866 Het-887 Het-868 Het-869 Het-870 Het-871 Het-872 Het-873 Het-874 0 Het-875 Het-876 Het-877 Het-878 Het-879 Het-880 Het-881 Het-882 Het-883 Het-884 0 Het-885 Het-886 Het-887 Het-888 Het-889 Het-890 Het-891 Het-892 Het-893 Het-894 0 Het-895 Het-896 Het-897 Het-898 Het-899 Het-900 Het-901 Het-902 Het-903 Het-904 0 Het-905 Het-906 Het-907 Het-908 Het-909 Het-910 Het-911 Het-912 Het-913 Het-914 00 Het-915 01 Het-916 02 Het-917 03 Het-918 04 Het-919 05 Het-920 06 Het-921 07 Het-922 08 Het-923 09 Het-924 0 Het-925 Het-926 Het-927 Het-928 Het-929 Het-930 Het-931 Het-932 Het-933 Het-934 0 Het-935 Het-936 Het-937 Het-938 Het-939 Het-940 Het-941 Het-942 Het-943 Het-944 0 Het-945 Het-946 Het-947 Het-948 Het-949 Het-950 Het-951 Het-952 Het-953 Het-954 0 Het-955 Het-956 Het-957 Het-958 Het-959 Het-960 Het-961 Het-982 Het-983 Het-964 0 Het-965 Het-966 Het-967 Het-968 Het-969 Het-970 Het-971 Het-972 Het-973 Het-974 0 Het-975 Het-976 Het-977 Het-978 Het-979 Het-980 Het-981 Het-982 Het-983 Het-984 0 Het-985 Het-986 Het-987 Het-988 Het-989 Het-990 Het-991 Het-992 Het-993 Het-994 0 Het-995 Het-996 Het-997 Het-998 Het-999 Het-1000 Het-1001 Het-1002 Het-1003 Het-1004 0 Het-1005 Het-1006 Het-1007 Het-1008 Het-1009 Het-1010 Het-1011 Het-1012 Het-1013 Het-1014 00 Het-1015 01 Het-1016 02 Het-1017 03 Het-1018 04 Het-1019 05 Het-1020 06 Het-1021 07 Het-1022 08 Het-1023 09 Het-1024 0 Het-1025 Het-1026 Het-1027 Het-1028 Het-1029 Het-1030 Het-1031 Het-1032 Het-1033 Het-1034 0 Het-1035 Het-1036 Het-1037 Het-1038 Het-1039 Het-1040 Het-1041 Het-1042 Het-1043 Het-1044 0 Het-1045 Het-1046 Het-1047 Het-1048 Het-1049 Het-1050 Het-1051 Het-1052 Het-1053 Het-1054 0 Het-1055 Het-1056 Het-1057 Het-1058 Het-1059 Het-1060 Het-1061 Het-1062 Het-1063 Het-1064 0 Het-1065 Het-1066 Het-1067 Het-1068 Het-1069 Het-1070 Het-1071 Het-1072 Het-1073 Het-1074 0 Het-1075 Het-1076 Het-1077 Het-1078 Het-1079 Het-1080 Het-1081 Het-1082 Het-1083 Het-1084 0 Het-1085 Het-1086 Het-1087 Het-1088 Het-1089 Het-1090 Het-1091 Het-1092 Het-1093 Het-1094 0 Het-1095 Het-1096 Het-1097 Het-1098 Het-1099 Het-1100 Het-1101 Het-1102 Het-1103 Het-1104 0 Het-1105 Het-1106 Het-1107 Het-1108 Het-1109 Het-1110 Het-1111 Het-1112 Het-1113 Het-1114 00 Het-1115 01 Het-1116 02 Het-1117 03 Het-1118 04 Het-1119 05 Het-1120 06 Het-1121 07 Het-1122 08 Het-1123 09 Het-1124 0 Het-1125 Het-1126 Het-1127 Het-1128 Het-1129 Het-1130 Het-1131 Het-1132 Het-1133 Het-1134 0 Het-1135 Het-1136 Het-1137 Het-1138 Het-1139 Het-1140 Het-1141 Het-1142 Het-1143 Het-1144 0 Het-1145 Het-1146 Het-1147 Het-1148 Het-1149 Het-1150 Het-1151 Het-1152 Het-1153 Het-1154 0 Het-1155 Het-1156 Het-1157 Het-1158 Het-1159 Het-1160 Het-1161 Het-1162 Het-1163 Het-1164 0 Het-1165 Het-1166 Het-1167 Het-1168 Het-1169 Het-1170 Het-1171 Het-1172 Het-1173 Het-1174 0 Het-1175 Het-1176 Het-1177 Het-1178 Het-1179 Het-1180 Het-1181 Het-1182 Het-1183 Het-1184 0 Het-1185 Het-1186 Het-1187 Het-1188 Het-1189 Het-1190 Het-1191 Het-1192 Het-1193 Het-1194 0 Het-1195 Het-1196 Het-1197 Het-1198 Het-1199 Het-1200 Het-1201 Het-1202 Het-1203 Het-1204 0 Het-1205 Het-1206 Het-1207 Het-1208 Het-1209 Het-1210 Het-1211 Het-1212 Het-1213 Het-1214 00 Het-1215 01 Het-1216 02 Het-1217 03 Het-1218 04 Het-1219 05 Het-1220 06 Het-1221 07 Het-1222 08 Het-1223 09 Het-1224 0 Het-1226 Het-1226 Het-1227 Het-1228 Het-1229 Het-1230 Het-1231 Het-1232 Het-1233 Het-1234 0 Het-1235 Het-1236 Het-1237 Het-1238 Het-1239 Het-1240 Het-1241 Het-1242 Het-1243 Het-1244 0 Het-1245 Het-1246 Het-1247 Het-1248 Het-1249 Het-1250 Het-1251 Het-1252 Het-1253 Het-1254 0 Het-1255 Het-1256 Het-1257 Het-1258 Het-1259 Het-1260 Het-1261 Het-1262 Het-1263 Het-1264 0 Het-1265 Het-1266 Het-1267 Het-1268 Het-1269 Het-1270 Het-1271 Het-1272 Het-1273 Het-1274 0 Het-1275 Het-1276 Het-1277 Het-1278 Het-1279 Het-1280 Het-1281 Het-1282 Het-1283 Het-1284 0 Het-1285 Het-1286 Het-1287 Het-1288 Het-1289 Het-1290 Het-1291 Het-1292 Het-1293 Het-1294 0 Het-1295 Het-1296 Het-1297 Het-1298 Het-1299 Het-1300 Het-1301 Het-1302 Het-1303 Het-1304 0 Het-1305 Het-1306 Het-1307 Het-1308 Het-1309 Het-1310 Het-1311 Het-1312 Het-1313 Het-1314 00 Het-1315 01 Het-1316 02 Het-1317 03 Het-1318 04 Het-1319 05 Het-1320 06 Het-1321 07 Het-1322 08 Het-1323 09 Het-1324 0 Het-1325 Het-1326 Het-1327 Het-1328 Het-1329 Het-1330 Het-1331 Het-1332 Het-1333 Het-1334 0 Het-1335 Het-1336 Het-1337 Het-1338 Het-1339 Het-1340 Het-1341 Het-1342 Het-1343 Het-1344 0 Het-1345 Het-1346 Het-1347 Het-1348 Het-1349 Het-1350 Het-1351 Het-1352 Het-1353 Het-1354 0 Het-1355 Het-1356 Het-1357 Het-1358 Het-1359 Het-1360 Het-1361 Het-1362 Het-1363 Het-1364 0 Het-1365 Het-1366 Het-1367 Het-1368 Het-1369 Het-1370 Het-1371 Het-1372 Het-1373 Het-1374 0 Het-1375 Het-1376 Het-1377 Het-1378 Het-1379 Het-1380 Het-1381 Het-1382 Het-1383 Het-1384 0 Het-1385 Het-1386 Het-1387 Het-1388 Het-1389 Het-1390 Het-1391 Het-1392 Het-1393 Het-1394 0 Het-1395 Het-1396 Het-1397 Het-1398 Het-1399 Het-1400 Het-1401 Het-1402 Het-1403 Het-1404 0 Het-1405 Het-1406 Het-1407 Het-1408 Het-1409 Het-1410 Het-1411 Het-1412 Het-1413 Het-1414 000 Het-1415 001 Het-1416 002 Het-1417 003 Het-1418 004 Het-1419 005 Het-1420 006 Het-1421 007 Het-1422 008 Het-1423 009 Het-1424 010 Het-1425 011 Het-1426 012 Het-1427 013 Het-1428 014 Het-1429 015 Het-1430 016 Het-1431 017 Het-1432 018 Het-1433 019 Het-1434 020 Het-1435 021 Het-1436 022 Het-1437 023 Het-1438 024 Het-1439 025 Het-1440 026 Het-1441 027 Het-1442 028 Het-1443 029 Het-1444 030 Het-1445 031 Het-1446 032 Het-1447 033 Het-1448 034 Het-1449 035 Het-1450 036 Het-1451 037 Het-1452 038 Het-1453 039 Het-1454 040 Het-1455 041 Het-1456 042 Het-1457 043 Het-1458 044 Het-1459 045 Het-1460 046 Het-1461 047 Het-1462 048 Het-1463 049 Het-1464 050 Het-1465 051 Het-1466 052 Het-1467 053 Het-1468 054 Het-1469 055 Het-1470 056 Het-1471 057 Het-1472 058 Het-1473 059 Het-1474 060 Het-1475 061 Het-1476 062 Het-1477 063 Het-1478 064 Het-1479 065 Het-1480 066 Het-1481 067 Het-1482 068 Het-1483 069 Het-1484 070 Het-1485 071 Het-1486 072 Het-1487 073 Het-1488 074 Het-1489 075 Het-1490 076 Het-1491 077 Het-1492 078 Het-1493 079 Het-1494 080 Het-1495 081 Het-1496 082 Het-1497 083 Het-1498 084 Het-1499 085 Het-1500 086 Het-1501 087 Het-1502 088 Het-1503 089 Het-1504 090 Het-1505 091 Het-1506 092 Het-1507 093 Het-1508 094 Het-1509 095 Het-1510 096 Het-1511 097 Het-1512 098 Het-1513 099 Het-1514 00 Het-1515 01 Het-1516 02 Het-1517 03 Het-1518 04 Het-1519 05 Het-1520 06 Het-1521 07 Het-1522 08 Het-1523 09 Het-1524 0 Het-1525 Het-1526 Het-1527 Het-1528 Het-1529 Het-1530 Het-1531 Het-1532 Het-1533 Het-1534 0 Het-1535 Het-1536 Het-1537 Het-1538 Het-1539 Het-1540 Het-1541 Het-1542 Het-1543 Het-1544 0 Het-1545 Het-1546 Het-1547 Het-1548 Het-1549 Het-1550 Het-1551 Het-1552 Het-1553 Het-1554 0 Het-1555 Het-1556 Het-1557 Het-1558 Het-1559 Het-1560 Het-1561 Het-1562 Het-1563 Het-1564 0 Het-1565 Het-1566 Het-1567 Het-1568 Het-1569 Het-1570 Het-1571 Het-1572 Het-1573 Het-1574 0 Het-1575 Het-1576 Het-1577 Het-1578 Het-1579 Het-1580 Het-1581 Het-1582 Het-1583 Het-1584 0 Het-1585 Het-1586 Het-1587 Het-1588 Het-1589 Het-1590 Het-1591 Het-1592 Het-1593 Het-1594 0 Het-1595 Het-1596 Het-1597 Het-1598 Het-1599 Het-1600 Het-1601 Het-1602 Het-1603 Het-1604 0 Het-1605 Het-1606 Het-1607 Het-1608 Het-1609 Het-1610 Het-1611 Het-1612 Het-1613 Het-1614 00 Het-1615 01 Het-1616 02 Het-1617 03 Het-1618 04 Het-1619 05 Het-1620 06 Het-1621 07 Het-1622 08 Het-1623 09 Het-1624 0 Het-1625 Het-1626 Het-1627 Het-1628 Het-1629 Het-1630 Het-1631 Het-1632 Het-1633 Het-1634 0 Het-1635 Het-1636 Het-1637 Het-1638 Het-1639 Het-1640 Het-1641 Het-1642 Het-1643 Het-1644 0 Het-1645 Het-1646 Het-1647 Het-1648 Het-1649 Het-1650 Het-1651 Het-1652 Het-1653 Het-1654 0 Het-1655 Het-1656 Het-1657 Het-1658 Het-1659 Het-1660 Het-1661 Het-1662 Het-1683 Het-1684 0 Het-1665 Het-1666 Het-1667 Het-1668 Het-1669 Het-1670 Het-1671 Het-1672 Het-1673 Het-1674 0 Het-1675 Het-1676 Het-1677 Het-1678 Het-1679 Het-1680 Het-1681 Het-1682 Het-1683 Het-1684 0 Het-1685 Het-1686 Het-1687 Het-1688 Het-1689 Het-1690 Het-1691 Het-1692 Het-1693 Het-1694 0 Het-1695 Het-1696 Het-1697 Het-1698 Het-1699 Het-1700 Het-1701 Het-1702 Het-1703 Het-1704 0 Het-1705 Het-1706 Het-1707 Het-1708 Het-1709 Het-1710 Het-1711 Het-1712 Het-1713 Het-1714 00 Het-1715 01 Het-1716 02 Het-1717 03 Het-1718 04 Het-1719 05 Het-1720 06 Het-1721 07 Het-1722 08 Het-1723 09 Het-1724 0 Het-1725 Het-1726 Het-1727 Het-1728 Het-1729 Het-1730 Het-1731 Het-1732 Het-1733 Het-1734 0 Het-1735 Het-1736 Het-1737 Het-1738 Het-1739 Het-1740 Het-1741 Het-1742 Het-1743 Het-1744 0 Het-1745 Het-1746 Het-1747 Het-1748 Het-1749 Het-1750 Het-1751 Het-1752 Het-1753 Het-1754 0 Het-1755 Het-1756 Het-1757 Het-1758 Het-1759 Het-1760 Het-1761 Het-1762 Het-1763 Het-1764 0 Het-1765 Het-1766 Het-1767 Het-1768 Het-1769 Het-1770 Het-1771 Het-1772 Het-1773 Het-1774 0 Het-1775 Het-1776 Het-1777 Het-1778 Het-1779 Het-1780 Het-1781 Het-1782 Het-1783 Het-1784 0 Het-1785 Het-1786 Het-1787 Het-1788 Het-1789 Het-1790 Het-1791 Het-1792 Het-1793 Het-1794 0 Het-1795 Het-1796 Het-1797 Het-1798 Het-1799 Het-1800 Het-1801 Het-1802 Het-1803 Het-1804 0 Het-1805 Het-1806 Het-1807 Het-1808 Het-1809 Het-1810 Het-1811 Het-1812 Het-1813 Het-1814 00 Het-1815 01 Het-1816 02 Het-1817 03 Het-1818 04 Het-1819 05 Het-1820 06 Het-1821 07 Het-1822 08 Het-1823 09 Het-1824 0 Het-1825 Het-1826 Het-1827 Het-1828 Het-1829 Het-1830 Het-1831 Het-1832 Het-1833 Het-1834 0 Het-1835 Het-1836 Het-1837 Het-1838 Het-1839 Het-1840 Het-1841 Het-1842 Het-1843 Het-1844 0 Het-1845 Het-1846 Het-1847 Het-1848 Het-1849 Het-1850 Het-1851 Het-1852 Het-1853 Het-1854 0 Het-1855 Het-1856 Het-1857 Het-1858 Het-1859 Het-1860 Het-1861 Het-1862 Het-1863 Het-1864 0 Het-1865 Het-1866 Het-1887 Het-1868 Het-1869 Het-1870 Het-1871 Het-1872 Het-1873 Het-1874 0 Het-1875 Het-1876 Het-1877 Het-1878 Het-1879 Het-1880 Het-1881 Het-1882 Het-1883 Het-1884 0 Het-1885 Het-1886 Het-1887 Het-1888 Het-1889 Het-1890 Het-1891 Het-1892 Het-1893 Het-1894 0 Het-1895 Het-1896 Het-1897 Het-1898 Het-1899 Het-1900 Het-1901 Het-1902 Het-1903 Het-1904 0 Het-1905 Het-1906 Het-1907 Het-1908 Het-1909 Het-1910 Het-1911 Het-1912 Het-1913 Het-1914 00 Het-1915 01 Het-1916 02 Het-1917 03 Het-1918 04 Het-1919 05 Het-1920 06 Het-1921 07 Het-1922 08 Het-1923 09 Het-1924 0 Het-1925 Het-1926 Het-1927 Het-1928 Het-1929 Het-1930 Het-1931 Het-1932 Het-1933 Het-1934 0 Het-1935 Het-1936 Het-1937 Het-1938 Het-1939 Het-1940 Het-1941 Het-1942 Het-1943 Het-1944 0 Het-1945 Het-1946 Het-1947 Het-1948 Het-1949 Het-1950 Het-1951 Het-1952 Het-1953 Het-1954 0 Het-1955 Het-1956 Het-1957 Het-1958 Het-1959 Het-1960 Het-1961 Het-1962 Het-1963 Het-1964 0 Het-1965 Het-1966 Het-1967 Het-1968 Het-1969 Het-1970 Het-1971 Het-1972 Het-1973 Het-1974 0 Het-1975 Het-1976 Het-1977 Het-1978 Het-1979 Het-1980 Het-1981 Het-1982 Het-1983 Het-1984 0 Het-1985 Het-1986 Het-1987 Het-1988 Het-1989 Het-1990 Het-1991 Het-1992 Het-1993 Het-1994 0 Het-1995 Het-1996 Het-1997 Het-1998 Het-1999 Het-2000 Het-2001 Het-2002 Het-2003 Het-2004 0 Het-2005 Het-2006 Het-2007 Het-2008 Het-2009 Het-2010 Het-2011 Het-2012 Het-2013 Het-2014 00 Het-2015 01 Het-2016 02 Het-2017 03 Het-2018 04 Het-2019 05 Het-2020 06 Het-2021 07 Het-2022 08 Het-2023 09 Het-2024 0 Het-2025 Het-2026 Het-2027 Het-2028 Het-2029 Het-2030 Het-2031 Het-2032 Het-2033 Het-2034 0 Het-2035 Het-2036 Het-2037 Het-2038 Het-2039 Het-2040 Het-2041 Het-2042 Het-2043 Het-2044 0 Het-2045 Het-2046 Het-2047 Het-2048 Het-2049 Het-2050 Het-2051 Het-2052 Het-2053 Het-2054 0 Het-2055 Het-2056 Het-2057 Het-2058 Het-2059 Het-2060 Het-2061 Het-2062 Het-2063 Het-2064 0 Het-2065 Het-2066 Het-2067 Het-2068 Het-2069 Het-2070 Het-2071 Het-2072 Het-2073 Het-2074 0 Het-2075 Het-2076 Het-2077 Het-2078 Het-2079 Het-2080 Het-2081 Het-2082 Het-2083 Het-2084 0 Het-2085 Het-2086 Het-2087 Het-2088 Het-2089 Het-2090 Het-2091 Het-2092 Het-2093 Het-2094 0 Het-2095 Het-2096 Het-2097 Het-2098 Het-2099 Het-2100 Het-2101 Het-2102 Het-2103 Het-2104 0 Het-2105 Het-2106 Het-2107 Het-2108 Het-2109 Het-2110 Het-2111 Het-2112 Het-2113 Het-2114 00 Het-2115 01 Het-2116 02 Het-2117 03 Het-2118 04 Het-2119 05 Het-2120 06 Het-2121 07 Het-2122 08 Het-2123 09 Het-2124 0 Het-2125 Het-2126 Het-2127 Het-2128 Het-2129 Het-2130 Het-2131 Het-2132 Het-2133 Het-2134 0 Het-2135 Het-2136 Het-2137 Het-2138 Het-2139 Het-2140 Het-2141 Het-2142 Het-2143 Het-2144 0 Het-2145 Het-2146 Het-2147 Het-2148 Het-2149 Het-2150 Het-2151 Het-2152 Het-2153 Het-2154 0 Het-2155 Het-2156 Het-2157 Het-2158 Het-2159 Het-2160 Het-2161 Het-2162 Het-2163 Het-2164 0 Het-2165 Het-2166 Het-2167 Het-2168 Het-2169 Het-2170 Het-2171 Het-2172 Het-2173 Het-2174 0 Het-2175 Het-2176 Het-2177 Het-2178 Het-2179 Het-2180 Het-2181 Het-2182 Het-2183 Het-2184 0 Het-2185 Het-2186 Het-2187 Het-2188 Het-2189 Het-2190 Het-2191 Het-2192 Het-2193 Het-2194 0 Het-2195 Het-2196 Het-2197 Het-2198 Het-2199 Het-2200 Het-2201 Het-2202 Het-2203 Het-2204 0 Het-2205 Het-2206 Het-2207 Het-2208 Het-2209 Het-2210 Het-2211 Het-2212 Het-2213 Het-2214 00 Het-2215 01 Het-2216 02 Het-2217 03 Het-2218 04 Het-2219 05 Het-2220 06 Het-2221 07 Het-2222 08 Het-2223 09 Het-2224 0 Het-2225 Het-2226 Het-2227 Het-2228 Het-2229 Het-2230 Het-2231 Het-2232 Het-2233 Het-2234 0 Het-2235 Het-2236 Het-2237 Het-2238 Het-2239 Het-2240 Het-2241 Het-2242 Het-2243 Het-2244 0 Het-2245 Het-2246 Het-2247 Het-2248 Het-2249 Het-2250 Het-2251 Het-2252 Het-2253 Het-2254 0 Het-2255 Het-2256 Het-2257 Het-2258 Het-2259 Het-2260 Het-2261 Het-2262 Het-2263 Het-2264 0 Het-2265 Het-2266 Het-2267 Het-2268 Het-2269 Het-2270 Het-2271 Het-2272 Het-2273 Het-2274 0 Het-2275 Het-2276 Het-2277 Het-2278 Het-2279 Het-2280 Het-2281 Het-2282 Het-2283 Het-2284 0 Het-2285 Het-2286 Het-2287 Het-2288 Het-2289 Het-2290 Het-2291 Het-2292 Het-2293 Het-2294 0 Het-2295 Het-2296 Het-2297 Het-2298 Het-2299 Het-2300 Het-2301 Het-2302 Het-2303 Het-2304 0 Het-2305 Het-2306 Het-2307 Het-2308 Het-2309 Het-2310 Het-2311 Het-2312 Het-2313 Het-2314 00 Het-2315 01 Het-2316 02 Het-2317 03 Het-2318 04 Het-2319 05 Het-2320 06 Het-2321 07 Het-2322 08 Het-2323 09 Het-2324 0 Het-2325 Het-2326 Het-2327 Het-2328 Het-2329 Het-2330 Het-2331 Het-2332 Het-2333 Het-2334 0 Het-2335 Het-2336 Het-2337 Het-2338 Het-2339 Het-2340 Het-2341 Het-2342 Het-2343 Het-2344 0 Het-2345 Het-2346 Het-2347 Het-2348 Het-2349 Het-2350 Het-2351 Het-2352 Het-2353 Het-2354 0 Het-2355 Het-2356 Het-2357 Het-2358 Het-2359 Het-2360 Het-2361 Het-2362 Het-2363 Het-2364 0 Het-2365 Het-2366 Het-2367 Het-2368 Het-2369 Het-2370 Het-2371 Het-2372 Het-2373 Het-2374 0 Het-2375 Het-2376 Het-2377 Het-2378 Het-2379 Het-2380 Het-2381 Het-2382 Het-2383 Het-2384 0 Het-2385 Het-2386 Het-2387 Het-2388 Het-2389 Het-2390 Het-2391 Het-2392 Het-2393 Het-2394 0 Het-2395 Het-2396 Het-2397 Het-2398 Het-2399 Het-2400 Het-2401 Het-2402 Het-2403 Het-2404 0 Het-2405 Het-2406 Het-2407 Het-2408 Het-2409 Het-2410 Het-2411 Het-2412 Het-2413 Het-2414 000 Het-2415 001 Het-2416 002 Het-2417 003 Het-2418 004 Het-2419 005 Het-2420 006 Het-2421 007 Het-2422 008 Het-2423 009 Het-2424 010 Het-2425 011 Het-2426 012 Het-2427 013 Het-2428 014 Het-2429 015 Het-2430 016 Het-2431 017 Het-2432 018 Het-2433 019 Het-2434 020 Het-2435 021 Het-2436 022 Het-2437 023 Het-2438 024 Het-2439 025 Het-2440 026 Het-2441 027 Het-2442 028 Het-2443 029 Het-2444 030 Het-2445 031 Het-2446 032 Het-2447 033 Het-2448 034 Het-2449 035 Het-2450 036 Het-2451 037 Het-2452 038 Het-2453 039 Het-2454 040 Het-2455 041 Het-2456 042 Het-2457 043 Het-2458 044 Het-2459 045 Het-2460 046 Het-2461 047 Het-2462 048 Het-2463 049 Het-2464 050 Het-2465 051 Het-2466 052 Het-2467 053 Het-2468 054 Het-2469 055 Het-2470 056 Het-2471 057 Het-2472 058 Het-2473 059 Het-2474 060 Het-2475 061 Het-2476 062 Het-2477 063 Het-2478 064 Het-2479 065 Het-2480 066 Het-2481 067 Het-2482 068 Het-2483 069 Het-2484 070 Het-2485 071 Het-2486 072 Het-2487 073 Het-2488 074 Het-2489 075 Het-2490 076 Het-2491 077 Het-2492 078 Het-2493 079 Het-2494 080 Het-2495 081 Het-2496 082 Het-2497 083 Het-2498 084 Het-2499 085 Het-2500 086 Het-2501 087 Het-2502 088 Het-2503 089 Het-2504 090 Het-2505 091 Het-2506 092 Het-2507 093 Het-2508 094 Het-2509 095 Het-2510 096 Het-2511 097 Het-2512 098 Het-2513 099 Het-2514 00 Het-2515 01 Het-2516 02 Het-2517 03 Het-2518 04 Het-2519 05 Het-2520 06 Het-2521 07 Het-2522 08 Het-2523 09 Het-2524 0 Het-2525 Het-2526 Het-2527 Het-2528 Het-2529 Het-2530 Het-2531 Het-2532 Het-2533 Het-2534 0 Het-2535 Het-2536 Het-2537 Het-2538 Het-2539 Het-2540 Het-2541 Het-2542 Het-2543 Het-2544 0 Het-2545 Het-2546 Het-2547 Het-2548 Het-2549 Het-2550 Het-2551 Het-2552 Het-2553 Het-2554 0 Het-2555 Het-2556 Het-2557 Het-2558 Het-2559 Het-2560 Het-2561 Het-2562 Het-2563 Het-2564 0 Het-2565 Het-2566 Het-2567 Het-2568 Het-2569 Het-2570 Het-2571 Het-2572 Het-2573 Het-2574 0 Het-2575 Het-2576 Het-2577 Het-2578 Het-2579 Het-2580 Het-2581 Het-2582 Het-2583 Het-2584 0 Het-2585 Het-2586 Het-2587 Het-2588 Het-2589 Het-2590 Het-2591 Het-2592 Het-2593 Het-2594 0 Het-2595 Het-2596 Het-2597 Het-2598 Het-2599 Het-2600 Het-2601 Het-2602 Het-2603 Het-2604 0 Het-2605 Het-2606 Het-2607 Het-2608 Het-2609 Het-2610 Het-2611 Het-2612 Het-2613 Het-2614 00 Het-2615 01 Het-2616 02 Het-2617 03 Het-2618 04 Het-2619 05 Het-2620 06 Het-2621 07 Het-2622 08 Het-2623 09 Het-2624 0 Het-2625 Het-2626 Het-2627 Het-2628 Het-2629 Het-2630 Het-2631 Het-2632 Het-2633 Het-2634 0 Het-2635 Het-2636 Het-2637 Het-2638 Het-2639 Het-2640 Het-2641 Het-2642 Het-2643 Het-2644 0 Het-2645 Het-2646 Het-2647 Het-2648 Het-2649 Het-2650 Het-2651 Het-2652 Het-2653 Het-2654 0 Het-2655 Het-2656 Het-2657 Het-2658 Het-2659 Het-2660 Het-2661 Het-2662 Het-2663 Het-2664 0 Het-2665 Het-2666 Het-2667 Het-2668 Het-2669 Het-2670 Het-2671 Het-2672 Het-2673 Het-2674 0 Het-2675 Het-2676 Het-2677 Het-2678 Het-2679 Het-2680 Het-2681 Het-2682 Het-2683 Het-2684 0 Het-2685 Het-2686 Het-2687 Het-2688 Het-2689 Het-2690 Het-2691 Het-2692 Het-2693 Het-2694 0 Het-2695 Het-2696 Het-2697 Het-2698 Het-2699 Het-2700 Het-2701 Het-2702 Het-2703 Het-2704 0 Het-2705 Het-2706 Het-2707 Het-2708 Het-2709 Het-2710 Het-2711 Het-2712 Het-2713 Het-2714 00 Het-2715 01 Het-2716 02 Het-2717 03 Het-2718 04 Het-2719 05 Het-2720 06 Het-2721 07 Het-2722 08 Het-2723 09 Het-2724 0 Het-2725 Het-2726 Het-2727 Het-2728 Het-2729 Het-2730 Het-2731 Het-2732 Het-2733 Het-2734 0 Het-2735 Het-2736 Het-2737 Het-2738 Het-2739 Het-2740 Het-2741 Het-2742 Het-2743 Het-2744 0 Het-2745 Het-2746 Het-2747 Het-2748 Het-2749 Het-2750 Het-2751 Het-2752 Het-2753 Het-2754 0 Het-2755 Het-2756 Het-2757 Het-2758 Het-2759 Het-2760 Het-2761 Het-2762 Het-2763 Het-2764 0 Het-2765 Het-2766 Het-2767 Het-2768 Het-2769 Het-2770 Het-2771 Het-2772 Het-2773 Het-2774 0 Het-2775 Het-2776 Het-2777 Het-2778 Het-2779 Het-2780 Het-2781 Het-2782 Het-2783 Het-2784 0 Het-2785 Het-2786 Het-2787 Het-2788 Het-2789 Het-2790 Het-2791 Het-2792 Het-2793 Het-2794 0 Het-2795 Het-2796 Het-2797 Het-2798 Het-2799 Het-2800 Het-2801 Het-2802 Het-2803 Het-2804 0 Het-2805 Het-2806 Het-2807 Het-2808 Het-2809 Het-2810 Het-2811 Het-2812 Het-2813 Het-2814 00 Het-2815 01 Het-2816 02 Het-2817 03 Het-2818 04 Het-2819 05 Het-2820 06 Het-2821 07 Het-2822 08 Het-2823 09 Het-2824 0 Het-2825 Het-2826 Het-2827 Het-2828 Het-2829 Het-2830 Het-2831 Het-2832 Het-2833 Het-2834 0 Het-2835 Het-2836 Het-2837 Het-2838 Het-2839 Het-2840 Het-2841 Het-2842 Het-2843 Het-2844 0 Het-2845 Het-2846 Het-2847 Het-2848 Het-2849 Het-2850 Het-2851 Het-2852 Het-2853 Het-2854 0 Het-2855 Het-2856 Het-2857 Het-2858 Het-2859 Het-2860 Het-2861 Het-2862 Het-2863 Het-2864 0 Het-2865 Het-2866 Het-2867 Het-2868 Het-2869 Het-2870 Het-2871 Het-2872 Het-2873 Het-2874 0 Het-2875 Het-2876 Het-2877 Het-2878 Het-2879 Het-2880

(435) In the following, examples of the methods for producing the compounds represented by Formula (1) will be illustrated. The methods for producing the compounds of the present invention are not limited to Production Method A to Production Method AJ.

(436) [Production Method A]

(437) ##STR03466##

(438) In the formula, R7 represents a hydrogen atom, a hydroxyl group, a cyano group, a C1-C6 alkyl group optionally substituted with substituent(s) A, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group optionally substituted with substituent(s) A, a C2-C6 alkenyl group optionally substituted with substituent(s) A, a C2-C6 haloalkenyl group, a C2-C6 alkynyl group optionally substituted with substituent(s) A, a C2-C6 haloalkynyl group, a C1-C6 alkoxy group optionally substituted with substituent(s) A, a C1-C6 haloalkoxy group, a C3-C8 cycloalkoxy group optionally substituted with substituent(s) A, a C2-C6 alkenyloxy group optionally substituted with substituent(s) A, a C2-C6 haloalkenyloxy group, a C3-C6 alkynyloxy group optionally substituted with substituent(s) A, a C3-C6 haloalkynyloxy group or RaRbN— (wherein Ra and Rb each independently represents a hydrogen atom, a C1-C6 alkyl group optionally substituted with substituent(s) B, a C1-C6 haloalkyl group or a C3-C8 cycloalkyl group or Ra and Rb together with the nitrogen atom to which they are bonded form an aziridinyl group, an azetidinyl group, a pyrrolidinyl group, a piperidinyl group, a homopiperidinyl group or an azocanyl group), R6 represents a hydrogen atom or a C1-C6 alkyl group, and R2, Het, X and Y are the same as defined hereinabove.

(439) Production Method A is a method for obtaining a compound represented by Formula (1b-a) including a compound of the present invention and a production intermediate of a compound of the present invention, and includes reacting a compound represented by Formula (3) with R7NH.sub.2 in the presence of an acid.

(440) The R7NH.sub.2 used in the present reaction can be obtained as a commercially available product or produced by a conventionally known method. The R7NH.sub.2 may be a material which forms a salt with an acidic compound such as hydrochloric acid and acetic acid, and is not particularly limited as long as the target reaction proceeds.

(441) The R7NH.sub.2 used in the present reaction may be 1 equivalent or more relative to the compound represented by Formula (3), and is not particularly limited as long as the target reaction proceeds, and is preferably 1 equivalent or more and 200 equivalents or less.

(442) The acids used in the present reaction may be exemplified by an inorganic acid such as hydrochloric acid, sulfuric acid and the like, and an organic acid such as acetic acid, methanesulfonic acid, p-toluenesulfonic acid and the like, and is not particularly limited as long as the target reaction proceeds, and preferably acetic acid. In addition, when a salt of the R7NH.sub.2 and the acidic compound is used, use of the acid is not essential.

(443) An amount of the acid used in the present reaction may be 1 equivalent or more relative to the R7NH.sub.2, and is not particularly limited as long as the target reaction proceeds, and preferably 1 equivalent or more and 200 equivalents or less. In addition, when the acid to be used is a liquid, it is possible to use it as a solvent.

(444) A solvent may be used in the present reaction, but it is not essential.

(445) The solvent to be used in the present reaction is not particularly limited as long as the target reaction proceeds, and may include acidic solvents such as acetic acid and methanesulfonic acid, ether solvents such as diethyl ether, diisopropyl ether, methyl-t-butyl ether, dimethoxyethane, tetrahydrofuran and dioxane, alcohol solvents such as methanol, ethanol and isopropanol, benzene based solvents such as benzene, toluene, xylene, mesitylene, chlorobenzene and dichlorobenzene, ester solvents such as ethyl acetate, isopropyl acetate and butyl acetate, nitrile solvents such as acetonitrile, amide solvents such as N-methylpyrrolidone, N,N-dimethylformamide and N,N-dimethylacetamide, urea solvents such as 1,3-dimethyl-2-imidazolidinone, halogen based solvents such as dichloromethane, dichloroethane, chloroform and carbon tetrachloride, and the like. These solvents may be used singly, or two or more kinds may be used in combination in an optional ratio. As the solvents, among others, acidic solvents are preferably mentioned, and acetic acid is more preferably mentioned.

(446) An amount of the solvent used in the present reaction is not particularly limited as long as the target reaction proceeds, and is usually 3 times by weight to 200 times by weight relative to the amount of the compound represented by Formula (3).

(447) A temperature to carry out the present reaction is not particularly limited as long as the target reaction proceeds, and is usually 50° C. or higher and 180° C. or lower or a boiling point of the solvent or lower.

(448) As a post treatment after the reaction, it is possible to carry out a liquid separating operation by adding water or a suitable aqueous solution to the reaction mixture. When an aqueous solution is to be used, an acidic aqueous solution in which hydrochloric acid, sulfuric acid, ammonium chloride or the like is dissolved, an alkaline aqueous solution in which potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate or the like is dissolved or a saline solution or the like can be optionally used. At the time of the liquid separating operation, if necessary, it is possible to add a solvent which is immiscible with water including benzene based solvents such as toluene, xylene, benzene, chlorobenzene and dichlorobenzene, ester solvents such as ethyl acetate, isopropyl acetate and butyl acetate, ether solvents such as diethyl ether, diisopropyl ether and methyl-t-butyl ether, halogen based solvents such as dichloromethane, dichloroethane, chloroform and carbon tetrachloride, hydrocarbon solvents such as hexane, heptane, cyclohexane and methylcyclohexane, and the like. In addition, it is possible to use these solvents singly or to mix two or more kinds with an optional ratio.

(449) The number of times of the liquid separation is not particularly limited, and may be carried out in accordance with the purity and yield to be desired.

(450) The reaction mixture obtained above which contains the compound represented by Formula (1b-a) may be dehydrated with a drying agent such as sodium sulfate and magnesium sulfate, but this is not essential.

(451) The reaction mixture obtained above which contains the compound represented by Formula (1b-a) may be distilled under reduced pressure to remove the solvent as long as the compound is not decomposed.

(452) The reaction mixture obtained after distillation of the solvent which contains the compound represented by Formula (1b-a) may be purified by washing, reprecipitation, recrystallization, column chromatography and the like, using a suitable solvent. It may be optionally set in accordance with the desired purity.

(453) According to Production Method A, a compound represented by Formula (2) which can be produced when R7 in a compound represented by Formula (1b-a) represents a hydrogen atom can be a useful production intermediate for obtaining a compound represented by Formula (1b) among the compounds of the present invention.

(454) Specific examples of the production intermediate represented by Formula (2) are shown by combinations of the structural formulae (I-1 to I-12) illustrated in Table 4, Y illustrated in Table 2, Het illustrated in Table 3, and X which is an oxygen atom or a sulfur atom. These compounds are only illustrative, and the present invention is not limited by these.

(455) [Table 4]

(456) TABLE-US-00004 TABLE 4 I-1 I-2 I-3 0 I-4 I-5 I-6 I-7 I-8 I-9 I-10 I-11 I-12

(457) A method for obtaining Formula (1b) of the present invention by utilizing the compound represented by Formula (2) as a production intermediate is described.

(458) [Production Method B]

(459) ##STR03479##

(460) In the formula, Lv represents a leaving group such as a methanesulfonyl group, a trifluoromethanesulfonyl group, a p-toluenesulfonyl group or a halogen atom, and R1, R2, Het, X and Y are the same as defined hereinabove.

(461) Production Method B is a method for obtaining a compound represented by Formula (1b), and is a production method which comprises reacting a production intermediate represented by Formula (2) with R1-Lv in the presence of a base in a solvent.

(462) The R1-Lv to be used in the present reaction can be obtained as a commercially available product or produced by a conventionally known method.

(463) An amount of the R1-Lv to be used in the present reaction may be 1 equivalent or more relative to the compound represented by Formula (2), which is not particularly limited as long as the target reaction proceeds, and preferably 1 equivalent or more and 10 equivalents or less.

(464) The base to be used in the present reaction may be exemplified by inorganic bases such as sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, cesium carbonate and sodium hydride, which is not particularly limited as long as the target reaction proceeds.

(465) An amount of the base to be used in the present reaction may be 1 equivalent or more relative to the compound represented by Formula (2), which is not particularly limited as long as the target reaction proceeds, preferably 1 equivalent or more and 10 equivalents or less.

(466) The solvent to be used in the present reaction is not particularly limited as long as the target reaction proceeds, and may include ether solvents such as diethyl ether, diisopropyl ether, methyl-t-butyl ether, dimethoxyethane, tetrahydrofuran and dioxane, alcohol solvents such as methanol, ethanol and isopropanol, benzene based solvents such as benzene, toluene, xylene, mesitylene, chlorobenzene and dichlorobenzene, ester solvents such as ethyl acetate, isopropyl acetate and butyl acetate, nitrile solvents such as acetonitrile, amide solvents such as N-methylpyrrolidone, N,N-dimethylformamide and N,N-dimethylacetamide, urea solvents such as 1,3-dimethyl-2-imidazolidinone, halogen based solvents such as dichloromethane, dichloroethane, chloroform and carbon tetrachloride, sulfur solvents such as dimethylsulfoxide and sulforane, ketone solvents such as acetone, methyl ethyl ketone and methyl isobutyl ketone, and the like.

(467) These solvents may be used singly, or two or more kinds may be used in combination in an optional ratio.

(468) An amount of the solvent to be used in the present reaction is not particularly limited as long as the target reaction proceeds, and is usually 3 times by weight or more and 200 times by weight or less relative to the compound represented by Formula (2).

(469) A temperature to carry out the present reaction is not particularly limited as long, as the target reaction proceeds, and is usually 0° C. or higher and 150° C. or lower or a boiling point of the solvent or lower.

(470) As a post treatment after the reaction, it is possible to carry out a liquid separating operation by adding water or a suitable aqueous solution to the reaction mixture. When an aqueous solution is to be used, an acidic aqueous solution in which hydrochloric acid, sulfuric acid, ammonium chloride or the like is dissolved, an alkaline aqueous solution in which potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate or the like is dissolved, an aqueous solution in which a salt containing a sulfur atom such as sodium thiosulfate, sodium sulfite or the like is dissolved or a saline solution or the like can be optionally used. At the time of the liquid separating operation, if necessary, it is possible to add a solvent which is immiscible with water including benzene based solvents such as toluene, xylene, benzene, chlorobenzene and dichlorobenzene, ester solvents such as ethyl acetate, isopropyl acetate and butyl acetate, ether solvents such as diethyl ether, diisopropyl ether and methyl-t-butyl ether, halogen based solvents such as dichloromethane, dichloroethane, chloroform and carbon tetrachloride, hydrocarbon solvents such as hexane, heptane, cyclohexane and methylcyclohexane, and the like. In addition, it is possible to use these solvents singly or to mix two or more kinds with an optional ratio. The number of times of the liquid separation is not particularly limited, and may be carried out in accordance with the purity and yield to be desired.

(471) The reaction mixture obtained above which contains the compound represented by Formula (1b) may be dehydrated with a drying agent such as sodium sulfate and magnesium sulfate, but this is not essential.

(472) The reaction mixture obtained above which contains the compound represented by Formula (1b) may be distilled under reduced pressure to remove the solvent as long as the compound is not decomposed.

(473) The reaction mixture obtained after distillation of the solvent which contains the compound represented by Formula (1b) may be purified by washing, reprecipitation, recrystallization, column chromatography and the like, using a suitable solvent. It may be optionally set in accordance with the desired purity.

(474) [Production Method C]

(475) ##STR03480##

(476) In the formula, SR represents a sulfurizing agent, and R1, R2, Het and Y are the same as defined hereinabove.

(477) Production Method C is a production method for obtaining a compound represented by Formula (1b-c) which belongs to the compounds represented by Formula (1b), and is a production method which comprises reacting a compound represented by Formula (1b-b) and a sulfurizing agent (SR) in a solvent.

(478) An example of the sulfurizing agent to be used in the present reaction may include Lawesson's reagent (2,4-bis(4-methoxyphenyl)-1,3-dithia-2,4-diphosphetane-2,4-disulfide) and the like.

(479) An amount of the sulfurizing agent to be used in the present reaction may be 0.5 equivalent or more relative to a compound represented by Formula (1b-b), which is not particularly limited as long as the target reaction proceeds, and preferably 1 equivalent or more and 10 equivalents or less.

(480) The solvent to be used in the present reaction is not particularly limited as long as the target reaction proceeds, and may include ether solvents such as diethyl ether, diisopropyl ether, methyl-t-butyl ether, dimethoxyethane, tetrahydrofuran and dioxane, benzene based solvents such as benzene, toluene, xylene, mesitylene, chlorobenzene and dichlorobenzene, and the like. These solvents may be used singly, or two or more kinds may be used in combination in an optional ratio.

(481) An amount of the solvent to be used in the present reaction is not particularly limited as long as the target reaction proceeds, and is usually 3 times by weight or more and 200 times by weight or less relative to the compound represented by Formula (1b-b).

(482) A temperature to carry out the present reaction is not particularly limited as long as the target reaction proceeds, and is usually 50° C. or higher and 180° C. or lower or a boiling point of the solvent or lower.

(483) As a post treatment after the reaction, it is possible to carry out a liquid separating operation by adding water or a suitable aqueous solution to the reaction mixture. When an aqueous solution is to be used, an acidic aqueous solution in which hydrochloric acid, sulfuric acid, ammonium chloride or the like is dissolved, an alkaline aqueous solution in which potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate or the like is dissolved or a saline solution or the like can be optionally used. At the time of the liquid separating operation, if necessary, it is possible to add a solvent which is immiscible with water including benzene based solvents such as toluene, xylene, benzene, chlorobenzene and dichlorobenzene, ester solvents such as ethyl acetate, isopropyl acetate and butyl acetate, ether solvents such as diethyl ether, diisopropyl ether and methyl-t-butyl ether, halogen based solvents such as dichloromethane, dichloroethane, chloroform and carbon tetrachloride, hydrocarbon solvents such as hexane, heptane, cyclohexane and methylcyclohexane, and the like. In addition, it is possible to use these solvents singly or to mix two or more kinds with an optional ratio. The number of times of the liquid separation is not particularly limited, and may be carried out in accordance with the purity and yield to be desired. Also, in the present reaction, the liquid separating operation is not essential.

(484) The reaction mixture obtained above which contains the compound represented by Formula (1b-c) may be dehydrated with a drying agent such as sodium sulfate and magnesium sulfate, but this is not essential.

(485) The reaction mixture obtained above which contains the compound represented by Formula (1b-c) may be distilled under reduced pressure to remove the solvent as long as the compound is not decomposed.

(486) The reaction mixture obtained after distillation of the solvent which contains the compound represented by Formula (1b-c) may be purified by washing, reprecipitation, recrystallization, column chromatography and the like, using a suitable solvent. It may be optionally set in accordance with the desired purity.

(487) [Production Method D]

(488) ##STR03481##

(489) In the formula, R2a represents a C1-C6 alkyl group optionally substituted with substituent(s) A, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group optionally substituted with substituent(s) A, a C2-C6 alkenyl group optionally substituted with substituent(s) A, a C2-C6 haloalkenyl group, a C2-C6 alkynyl group optionally substituted with substituent(s) A or C2-C6 haloalkynyl group, and R1, Het, Lv, X and Y are the same as defined hereinabove.

(490) Production Method D is a synthetic method of a compound represented by Formula (1b-e), which belongs to the compounds represented by Formula (1b), wherein R2a is a C1-C6 alkyl group optionally substituted with substituent(s) A, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group optionally substituted with substituent(s) A, a C2-C6 alkenyl group optionally substituted with substituent(s) A, a C2-C6 haloalkenyl group, a C2-C6 alkynyl group optionally substituted with substituent(s) A or a C2-C6 haloalkynyl group, and is a production method which comprises reacting a compound represented by Formula (1b-d) and R2a-Lv in the presence of a base in a solvent.

(491) The R2a-Lv to be used in the present reaction can be obtained as a commercially available product or produced by a conventionally known method.

(492) An amount of the R2a-Lv to be used in the present reaction may be 1 equivalent or more relative to the compound represented by Formula (1b-d), which is not particularly limited as long as the target reaction proceeds, and preferably 1 equivalent or more and 1.8 equivalents or less.

(493) The base to be used in the present reaction may be exemplified by metal hydrides such as sodium hydride, organolithiums such as methyllithium, butyllithium, sec-butyllithium, t-butyllithium and hexyllithium, metal amides such as lithium diisopropylamide, hexamethyldisilazane lithium, hexamethyldisilazane sodium and hexamethyldisilazane potassium.

(494) An amount of the base to be used in the present reaction may be 1 equivalent or more relative to the compound represented by Formula (1b-d), which is not particularly limited as long as the target reaction proceeds, and preferably 1 equivalent or more and 10 equivalents or less.

(495) The solvent to be used in the present reaction is not particularly limited as long as the target reaction proceeds, and may include ether solvents such as diethyl ether, diisopropyl ether, methyl-t-butyl ether, dimethoxyethane, tetrahydrofuran and dioxane, benzene based solvents such as benzene, toluene, xylene, mesitylene, chlorobenzene and dichlorobenzene, and the like. These solvents may be used singly, or two or more kinds may be used in combination in an optional ratio.

(496) An amount of the solvent to be used in the present reaction is not particularly limited as long as the target reaction proceeds, and is usually 3 times by weight or more and 200 times by weight or less relative to the compound represented by Formula (1b-d).

(497) A temperature to carry out the present reaction is not particularly limited as long as the target reaction proceeds, and is usually −80° C. or higher and 100° C. or lower or a boiling point of the solvent or lower.

(498) As a post treatment after the reaction, it is possible to carry out a liquid separating operation by adding water or a suitable aqueous solution to the reaction mixture. When an aqueous solution is to be used, an acidic aqueous solution in which hydrochloric acid, sulfuric acid, ammonium chloride or the like is dissolved, an alkaline aqueous solution in which potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate or the like is dissolved, an aqueous solution in which a salt containing a sulfur atom such as sodium thiosulfate, sodium sulfite or the like is dissolved or a saline solution or the like can be optionally used. At the time of the liquid separating operation, if necessary, it is possible to add a solvent which is immiscible with water including benzene based solvents such as toluene, xylene, benzene, chlorobenzene and dichlorobenzene, ester solvents such as ethyl acetate, isopropyl acetate and butyl acetate, ether solvents such as diethyl ether, diisopropyl ether and methyl-t-butyl ether, halogen based solvents such as dichloromethane, dichloroethane and chloroform, hydrocarbon solvents such as hexane, heptane, cyclohexane and methylcyclohexane, and the like. In addition, it is possible to use these solvents singly or to mix two or more kinds with an optional ratio. The number of times of the liquid separation is not particularly limited, and may be carried out in accordance with the purity and yield to be desired.

(499) The reaction mixture obtained above which contains the compound represented by Formula (1b-e) may be dehydrated with a drying agent such as sodium sulfate and magnesium sulfate, but this is not essential.

(500) The reaction mixture obtained above which contains the compound represented by Formula (1b-e) may be distilled under reduced pressure to remove the solvent as long as the compound is not decomposed.

(501) The reaction mixture obtained after distillation of the solvent which contains the compound represented by Formula (1b-e) may be purified by washing, reprecipitation, recrystallization, column chromatography and the like, using a suitable solvent. It may be optionally set in accordance with the desired purity.

(502) [Production Method E]

(503) ##STR03482##

(504) In the formula, Ox represents an oxidizing agent, and R1, R2, Het, X and Y are the same as defined hereinabove.

(505) Production Method E is a method for obtaining a compound represented by Formula (1a), and is a production method which comprises reacting a compound represented by Formula (1b) and an oxidizing agent (Ox) in a solvent.

(506) The oxidizing agent to be used in the present reaction may include metal oxides such as manganese dioxide, benzoquinones such as 2,3-dichloro-5,6-dicyano-p-benzoquinone, a combination of a radical initiator such as azobisisobutyronitrile, 2,2′-azobis(4-methoxy-2,4-dimethylvaleryonitrile) and benzoyl peroxide, and a halogenating agent such as N-chlorosuccinimide, N-bromosuccinimide, N-iodosuccinimide, 1,3-dichloro-5,5-dimethylhydantoin, 1,3-dibromo-5,5-dimethylhydantoin and 1,3-diiodo-5,5-dimethylhydantoin.

(507) In the following, a method in which the oxidizing agent is a metal oxide will be described.

(508) An amount of the oxidizing agent to be used in the present reaction may be 1 equivalent or more relative to the compound represented by Formula (1b), which is not particularly limited as long as the target reaction proceeds, and is usually 1 equivalent or more and 200 equivalents or less.

(509) The solvent to be used in the present reaction is not particularly limited as long as the target reaction proceeds, and may include benzene based solvents such as benzene, toluene, xylene, mesitylene, chlorobenzene and dichlorobenzene, halogen based solvents such as dichloromethane, dichloroethane, chloroform and carbon tetrachloride, and the like. These solvents may be used singly, or two or more kinds may be used in combination in an optional ratio.

(510) An amount of the solvent to be used in the present reaction is not particularly limited as long as the target reaction proceeds, and is usually 3 times by weight or more and 200 times by weight or less relative to the compound represented by Formula (1b).

(511) A temperature to carry out the present reaction is not particularly limited as long as the target reaction proceeds, and is usually 0° C. or higher and 150° C. or lower or a boiling point of the solvent or lower.

(512) As a post treatment after the reaction; it is possible to remove undissolved metal by filtration. Further, it is possible to carry out a liquid separating operation by adding water or a suitable aqueous solution to the reaction mixture. When an aqueous solution is to be used, an acidic aqueous solution in which hydrochloric acid, sulfuric acid, ammonium chloride or the like is dissolved, an alkaline aqueous solution in which potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate or the like is dissolved or a saline solution or the like can be optionally used. At the time of the liquid separating operation, if necessary, it is possible to add a solvent which is immiscible with water including benzene based solvents such as toluene, xylene, benzene, chlorobenzene and dichlorobenzene, ester solvents such as ethyl acetate, isopropyl acetate and butyl acetate, ether solvents, such as diethyl ether, diisopropyl ether and methyl-t-butyl ether, halogen based solvents such as dichloromethane, dichloroethane, chloroform and carbon tetrachloride, hydrocarbon solvents such as hexane, heptane, cyclohexane and methylcyclohexane, and the like. In addition, it is possible to use these solvents singly or to mix two or more kinds with an optional ratio. The number of times of the liquid separation is not particularly limited, and may be carried out in accordance with the purity and yield to be desired. Also, in the present reaction, the liquid separating operation is not essential.

(513) The reaction mixture obtained above which contains the compound represented by Formula (1a) may be dehydrated with a drying agent such as sodium sulfate and magnesium sulfate, but this is not essential.

(514) The reaction mixture obtained above which contains the compound represented by Formula (1a) may be distilled off under reduced pressure to remove the solvent as long as the compound is not decomposed.

(515) The reaction mixture obtained after distillation of the solvent which contains the compound represented by Formula (1a) may be purified by washing, reprecipitation, recrystallization, column chromatography and the like, using a suitable solvent. It may be optionally set in accordance with the desired purity.

(516) In the following, a method in which the oxidizing agent is a benzoquinone will be described.

(517) An amount of the oxidizing agent to be used in the present reaction may be 1 equivalent or more relative to the compound represented by Formula (1b), which is not particularly limited as long as the target reaction proceeds, and is usually 1 equivalent or more and 20 equivalents or less.

(518) The solvent to be used in the present reaction is not particularly limited as long as the target reaction proceeds, and may include benzene based solvents such as benzene, toluene, xylene, mesitylene, chlorobenzene and dichlorobenzene, halogen based solvents such as dichloromethane, dichloroethane, chloroform and carbon tetrachloride, and the like. These solvents may be used singly, or two or more kinds may be used in combination in an optional ratio.

(519) An amount of the solvent to be used in the present reaction is not particularly limited as long as the target reaction proceeds, and is usually 3 times by weight or more and 200 times by weight or less relative to the compound represented by Formula (1b).

(520) A temperature to carry out the present reaction is not particularly limited as long as the target reaction proceeds, and is usually 0° C. or higher and 150° C. or lower or a boiling point of the solvent or lower.

(521) As a post treatment after the reaction, it is possible to carry out a liquid separating operation by adding water or a suitable aqueous solution to the reaction mixture. When an aqueous solution is to be used, an acidic aqueous solution in which hydrochloric acid, sulfuric acid, ammonium chloride or the like is dissolved, an alkaline aqueous solution in which potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate or the like is dissolved or a saline solution or the like can be optionally used. At the time of the liquid separating operation, if necessary, it is possible to add a solvent which is immiscible with water including benzene based solvents such as toluene, xylene, benzene, chlorobenzene and dichlorobenzene, ester solvents such as ethyl acetate, isopropyl acetate and butyl acetate, ether solvents such as diethyl ether, diisopropyl ether and methyl-t-butyl ether, halogen based solvents such as dichloromethane, dichloroethane, chloroform and carbon tetrachloride, hydrocarbon solvents such as hexane, heptane, cyclohexane and methylcyclohexane, and the like. In addition, it is possible to use these solvents singly or to mix two or more kinds with an optional ratio. The number of times of the liquid separation is not particularly limited, and may be carried out in accordance with the purity and yield to be desired. Also, in the present reaction, the liquid separating operation is not essential.

(522) The reaction mixture obtained above which contains the compound represented by Formula (1a) may be dehydrated with a drying agent such as sodium sulfate and magnesium sulfate, but this is not essential.

(523) The reaction mixture obtained above which contains the compound represented by Formula (1a) may be distilled under reduced pressure to remove the solvent as long as the compound is not decomposed.

(524) The reaction mixture obtained after distillation of the solvent which contains the compound represented by Formula (1a) may be purified by washing, reprecipitation, recrystallization, column chromatography and the like, using a suitable solvent. It may be optionally set in accordance with the desired purity.

(525) In the following, a method in which the oxidizing agent is a combination of a radical initiator and a halogenating agent will be described.

(526) Each amount of the radical initiator and the halogenating agent to be used in the present reaction is 0.01 equivalent or more and 1.0 equivalent or more relative to the compound represented by Formula (1b), respectively, and is not particularly limited as long as the target reaction proceeds. The radical initiator is preferably 0.01 equivalent or more and 1 equivalent or less, and the halogenating agent is 1 equivalent or more and 3 equivalents or less.

(527) The solvent to be used in the present reaction is not particularly limited as long as the target reaction proceeds, and may include halogenated benzene solvents such as chlorobenzene and dichlorobenzene, ester solvents such as ethyl acetate, isopropyl acetate and butyl acetate, halogen based solvents such as dichloromethane, dichloroethane, chloroform and carbon tetrachloride, hydrocarbon solvents such as hexane, heptane, cyclohexane and methylcyclohexane, and the like. These solvents may be used singly, or two or more kinds may be used in combination in an optional ratio.

(528) An amount of the solvent to be used in the present reaction is not particularly limited as long as the target reaction proceeds, and is usually 3 times by weight or more and 200 times by weight or less relative to the compound represented by Formula (1b).

(529) A temperature to carry out the present reaction is not particularly limited as long as the target reaction proceeds, and is usually 20° C. or higher and 150° C. or lower or a boiling point of the solvent or lower.

(530) As a post treatment after the reaction, it is possible to carry out a liquid separating operation by adding water or a suitable aqueous solution to the reaction mixture. When an aqueous solution is to be used, an acidic aqueous solution in which hydrochloric acid, sulfuric acid, ammonium chloride or the like is dissolved, an alkaline aqueous solution in which potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate or the like is dissolved, an aqueous solution in which a salt containing a sulfur atom such as sodium thiosulfate, sodium sulfite or the like is dissolved or a saline solution or the like can be optionally used. At the time of the liquid separating operation, if necessary, it is possible to add a solvent which is immiscible with water including benzene based solvents such as toluene, xylene, benzene, chlorobenzene and dichlorobenzene, ester solvents such as ethyl acetate, isopropyl acetate and butyl acetate, ether solvents such as diethyl ether, diisopropyl ether and methyl-t-butyl ether, halogen based solvents such as dichloromethane, dichloroethane and chloroform, hydrocarbon solvents such as hexane, heptane, cyclohexane and methylcyclohexane, and the like. In addition, it is possible to use these solvents singly or to mix two or more kinds with an optional ratio. The number of times of the liquid separation is not particularly limited, and may be carried out in accordance with the purity and yield to be desired.

(531) The reaction mixture obtained above which contains the compound represented by Formula (1a) may be dehydrated with a drying agent such as sodium sulfate and magnesium sulfate, but this is not essential.

(532) The reaction mixture obtained above which contains the compound represented by Formula (1a) may be distilled under reduced pressure to remove the solvent as long as the compound is not decomposed.

(533) The reaction mixture obtained after distillation of the solvent which contains the compound represented by Formula (1a) may be purified by washing, reprecipitation, recrystallization, column chromatography and the like, using a suitable solvent. It may be optionally set in accordance with the desired purity.

(534) [Production Method F]

(535) ##STR03483##

(536) In the formula, R2b represents a halogen atom, HalR represents a halogenating agent, and R1, Het, X and Y are the same as defined hereinabove.

(537) Production Method F is a production method for obtaining a compound represented by Formula (1a-b), which belongs to the compounds represented by Formula (1a), wherein R2b represents a halogen atom, and is a production method which comprises reacting a compound represented by Formula (1a-a) and a halogenating agent (HalR) in a solvent.

(538) The halogenating agent to be used in the present reaction may include Selectfluor (N-fluoro-N′-triethylenediamine bis(tetrafluoroborate)), N-chlorosuccinimide, N-bromosuccinimide, N-iodosuccinimide, 1,3-dichloro-5,5-dimethylhydantoin, 1,3-dibromo-5,5-dimethylhydantoin, 1,3-diiodo-5,5-dimethylhydantoin, bromine, iodine and the like.

(539) An amount of the halogenating agent to be used in the present reaction may be 1 equivalent or more relative to the compound represented by Formula (1a-a), which is not particularly limited as long as the target reaction proceeds, and preferably 1 equivalent or more and 10 equivalents or less. If the amount of the halogenating agent including hydantoin is 0.5 equivalent or more, it is not particularly limited as long as the target reaction proceeds, and preferably 1 equivalent or more and 5 equivalents or less.

(540) When the halogenating agent to be used in the present reaction is an iodinating agent, an acid including an inorganic acid such as hydrochloric acid, sulfuric acid or the like, or an organic acid such as acetic acid, trifluoroacetic acid, methanesulfonic acid, trifluoromethanesulfonic acid or the like may be added.

(541) An amount of the acid to be used when the halogenating agent to be used in the present reaction is the iodinating agent may be 0.01 equivalent or more relative to the compound represented by Formula (1a-a), which is not particularly limited as long as the target reaction proceeds, and preferably 0.1 equivalent or more and 3 equivalents or less.

(542) The solvent to be used in the present reaction is not particularly limited as long as the target reaction proceeds, and may include acidic solvents such as sulfuric acid, acetic acid, trifluoroacetic acid, methanesulfonic acid and trifluoromethanesulfonic acid, ether solvents such as diethyl ether, diisopropyl ether, methyl-t-butyl ether, dimethoxyethane, tetrahydrofuran and dioxane, alcohol solvents such as methanol, ethanol and isopropanol, benzene based solvents such as benzene, toluene, xylene, mesitylene, chlorobenzene and dichlorobenzene, ester solvents such as ethyl acetate, isopropyl acetate and butyl acetate, nitrile solvents such as acetonitrile, amide solvents such as N-methylpyrrolidone, N,N-dimethylformamide and N,N-dimethylacetamide, urea solvents such as 1,3-dimethyl-2-imidazolidinone, halogen based solvents such as dichloromethane, dichloroethane, chloroform and carbon tetrachloride, and the like.

(543) These solvents may be used singly, or two or more kinds may be used in combination in an optional ratio.

(544) An amount of the solvent to be used in the present reaction is not particularly limited as long as the target reaction proceeds, and is usually 3 times by weight or more and 200 times by weight or less relative to the compound represented by Formula (1a-a).

(545) A temperature to carry out the present reaction is not particularly limited as long as the target reaction proceeds, and is usually 0° C. or higher and 150° C. or lower or a boiling point of the solvent or lower.

(546) As a post treatment after the reaction, it is possible to carry out a liquid separating operation by adding water or a suitable aqueous solution to the reaction mixture. When an aqueous solution, is to be used, an acidic aqueous solution in which hydrochloric acid, sulfuric acid, ammonium chloride or the like is dissolved, an alkaline aqueous solution in which potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate or the like is dissolved, an aqueous solution in which a salt containing a sulfur atom such as sodium thiosulfate, sodium sulfite or the like is dissolved or a saline solution or the like can be optionally used. At the time of the liquid separating operation, if necessary, it is possible to add a solvent which is immiscible with water including benzene based solvents such as toluene, xylene, benzene, chlorobenzene and dichlorobenzene, ester solvents such as ethyl acetate, isopropyl acetate and butyl acetate, ether solvents such as diethyl ether, diisopropyl ether and methyl-t-butyl ether, halogen based solvents such as dichloromethane, dichloroethane, chloroform and carbon tetrachloride, hydrocarbon solvents such as hexane, heptane, cyclohexane and methylcyclohexane, and the like. In addition, it is possible to use these solvents singly or to mix two or more kinds with an optional ratio. The number of times of the liquid separation is not particularly limited, and may be carried out in accordance with the purity and yield to be desired.

(547) The reaction mixture obtained above which contains the compound represented by Formula (1a-b) may be dehydrated with a drying agent such as sodium sulfate and magnesium sulfate, but this is not essential.

(548) The reaction mixture obtained above which contains the compound represented by Formula (1a-b) may be distilled under reduced pressure to remove the solvent as long as the compound is not decomposed.

(549) The reaction mixture obtained after distillation of the solvent which contains the compound represented by Formula (1a-b) may be purified by washing, reprecipitation, recrystallization, column chromatography and the like, using a suitable solvent. It may be optionally set in accordance with the desired purity.

(550) [Production Method G]

(551) ##STR03484##

(552) In the formula, J represents an oxygen atom or a sulfur atom, when J is an oxygen atom, R2c represents a C1-C6 alkyl group optionally substituted with substituent(s) A, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group optionally substituted with substituent(s) A, a C2-C6 alkenyl group optionally substituted with substituent(s) A, a C2-C6 haloalkenyl group, a C3-C6 alkynyl group optionally substituted with substituent(s) A or a C3-C6 haloalkynyl group, when J is a sulfur atom, R2c represents a C1-C6 alkyl group or a C1-C6 haloalkyl group, Q represents a hydrogen atom or a metal, and R1, Het, R2b, X and Y are the same as defined hereinabove.

(553) Production Method G is a synthetic method of a compound represented by Formula (1a-c), which belongs to the compounds represented by Formula (1a), wherein J represents an oxygen atom or a sulfur atom, when J is an oxygen atom, R2c represents a C1-C6 alkyl group optionally substituted with substituent(s) A, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group optionally substituted with substituent(s) A, a C2-C6 alkenyl group optionally substituted with substituent(s) A, a C2-C6 haloalkenyl group, a C3-C6 alkynyl group optionally substituted with substituent(s) A or a C3-C6 haloalkynyl group, and when J is a sulfur atom, R2c represents a C1-C6 alkyl group or a C1-C6 haloalkyl group, and is a production method which comprises a coupling reaction wherein a compound represented by Formula (1a-b) and R2c-J-Q are reacted in the presence of a transition metal and a base in a solvent.

(554) Among the compounds represented by Formula (1a-b), preferable R2b is a chlorine atom, a bromine atom or an iodine atom.

(555) The R2c-J-Q to be used in the present reaction can be obtained as a commercially available product or produced by a conventionally known method. Preferable Q is a hydrogen atom or an alkali metal such as sodium, potassium and the like.

(556) An amount of the R2c-J-Q to be used in the present reaction may be 1 equivalent or more relative to the compound represented by Formula (1a-b), and is not particularly limited as long as the target reaction proceeds. When Q is a hydrogen atom, it can be also used as a solvent.

(557) The transition metal to be used in the present reaction may have a ligand, and may include palladiums such as palladium acetate, [1,1′-bis(diphenylphosphine)ferrocene]palladium dichloride, tris(dibenzylideneacetone)dipalladium, tetrakis(triphenylphosphine)palladium, bis(triphenylphosphine)palladium dichloride and the like.

(558) An amount of the transition metal to be used in the present reaction may be 0.001 equivalent or more and 1 equivalent or less relative to the compound represented by Formula (1a-b), and is not particularly limited as long as the target reaction proceeds.

(559) In order to proceed the present reaction efficiently, a phosphine ligand such as triphenylphosphine, 1,1′-bis(diphenylphosphine)ferrocene, 2-dicyclohexylphosphino-2′4′6′-triisopropylbiphenyl, 2-di-t-butylphosphino-2′4′6′-triisopropylbiphenyl and the like may be added.

(560) An amount of the phosphine ligand to be used in the present reaction may be 0.001 equivalent or more and 1 equivalent or less relative to the compound represented by Formula (1a-b), and is not particularly limited as long as the target reaction proceeds.

(561) The base to be used in the present reaction may include inorganic bases such as sodium carbonate, potassium carbonate and cesium carbon and organic bases such as triethylamine, tributylamine and diisopropylethylamine.

(562) An amount of the base to be used in the present reaction may be 1 equivalent or more relative to the compound represented by Formula (1a-b), which is not particularly limited as long as the target reaction proceeds, and preferably 1 equivalent or more and 50 equivalents or less.

(563) The solvent to be used in the present reaction is not particularly limited as long as the target reaction proceeds, and may include alcohol solvents represented by R2c-J-H (wherein R2c is the same as defined hereinabove, and J is an oxygen atom), ether solvents such as diethyl ether, diisopropyl ether, methyl-t-butyl ether, dimethoxyethane, tetrahydrofuran and dioxane, and benzene based solvents such as benzene, toluene, xylene, mesitylene, chlorobenzene and dichlorobenzene, and the like.

(564) These solvents may be used singly, or two or more kinds may be used in combination in an optional ratio.

(565) An amount of the solvent to be used in the present reaction is not particularly limited as long as the target reaction proceeds, and is usually 3 times by weight or more and 200 times by weight or less relative to the compound represented by Formula (1a-b).

(566) A temperature to carry out the present reaction is not particularly limited as long as the target reaction proceeds, and is usually 30° C. or higher and 200° C. or lower or a boiling point of the solvent or lower.

(567) As a post treatment after the reaction, it is possible to carry out a liquid separating operation by adding water or a suitable aqueous solution to the reaction mixture. When an aqueous solution is to be used, an acidic aqueous solution in which hydrochloric acid, sulfuric acid, ammonium chloride or the like is dissolved, an alkaline aqueous solution in which potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate or the like is dissolved or a saline solution or the like can be optionally used. At the time of the liquid separating operation, if necessary, it is possible to add a solvent which is immiscible with water including benzene based solvents such as toluene, xylene, benzene, chlorobenzene and dichlorobenzene, ester solvents such as ethyl acetate, isopropyl acetate and butyl acetate, ether solvents such as diethyl ether, diisopropyl ether and methyl-t-butyl ether, halogen based solvents such as dichloromethane, dichloroethane, chloroform and carbon tetrachloride, hydrocarbon solvents such as hexane, heptane, cyclohexane and methylcyclohexane, and the like. In addition, it is possible to use these solvents singly or to mix two or more kinds with an optional ratio. The number of times of the liquid separation is not particularly limited, and may be carried out in accordance with the purity and yield to be desired. In addition, it is also possible to remove insoluble materials by subjecting to filtration operation but it is not essential.

(568) The reaction mixture obtained above which contains the compound represented by Formula (1a-c) may be dehydrated with a drying agent such as sodium sulfate and magnesium sulfate, but this is not essential.

(569) The reaction mixture obtained above which contains the compound represented by Formula (1a-c) may be distilled under reduced pressure to remove the solvent as long as the compound is not decomposed.

(570) The reaction mixture obtained after distillation of the solvent which contains the compound represented by Formula (1a-c) may be purified by washing, reprecipitation, recrystallization, column chromatography and the like, using a suitable solvent. It may be optionally set in accordance with the desired purity.

(571) [Production Method H]

(572) ##STR03485##

(573) In the formula, R2d represents a C1-C6 alkyl group optionally substituted with substituent(s) A, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group optionally substituted with substituent(s) A, a C2-C6 alkenyl group optionally substituted with substituent(s) A or a C2-C6 haloalkenyl group, R2d-B represents organic boronic acids, and R1, Het, R2b, X and Y are the same as defined hereinabove.

(574) Production Method H is a synthetic method of a compound represented by Formula (1a-d), which belongs to the compounds represented by Formula (1a), wherein R2d is a C1-C6 alkyl group optionally substituted with substituent(s) A, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group optionally substituted with substituent(s) A, a C2-C6 alkenyl group optionally substituted with substituent(s) A or a C2-C6 haloalkenyl group, and is a production method which comprises Suzuki-Miyaura coupling wherein a compound represented by Formula (1a-b) and an organic boronic acid (R2d-B) are reacted in the presence of a transition metal and a base in a solvent.

(575) In Formula (1a-b), preferable R2b is a chlorine atom, a bromine atom or an iodine atom.

(576) The R2d-B to be used in the present reaction represents organic boronic acids such as an organic boronic acid, organic boronic acid ester and the like, and can be obtained as a commercially available product or produced by a conventionally known method.

(577) An amount of the R2d-B to be used in the present reaction may be 1 equivalent or more relative to the compound represented by Formula (1a-b), which is not particularly limited as long as the target reaction proceeds, and preferably 1 equivalent or more and 10 equivalents or less.

(578) The transition metal to be used in the present reaction may be palladium, nickel, ruthenium and the like, which may have a ligand(s). It may preferably include palladiums such as palladium acetate, [1,1′-bis(diphenylphosphine)ferrocene]palladium dichloride, tris(dibenzylideneacetone)dipalladium, tetrakis(triphenylphosphine)palladium, bis(triphenylphosphine)palladium dichloride and the like.

(579) An amount of the transition metal to be used in the present reaction may be 0.001 equivalent or more and 1 equivalent or less relative to the compound represented by Formula (1a-b), and is not particularly limited as long as the target reaction proceeds.

(580) In order to proceed the reaction efficiently, a phosphine ligand such as triphenylphosphine, tricyclohexylphosphine and the like may be added.

(581) An amount of the phosphine ligand to be used in the present reaction may be 0.001 equivalent or more and 1 equivalent or less relative to the compound represented by Formula (1a-b), and is not particularly limited as long as the target reaction proceeds.

(582) The base to be used in the present reaction may include inorganic bases such as sodium carbonate, potassium carbonate, cesium carbonate and tripotassium phosphate, and metal alkoxides such as sodium methoxide, sodium ethoxide and potassium t-butoxide.

(583) An amount of the base to be used in the present reaction may be 1 equivalent or more relative to the compound represented by Formula (1a-b), which is not particularly limited as long as the target reaction proceeds, and preferably 1 equivalent or more and 50 equivalents or less.

(584) The solvent to be used in the present reaction is not particularly limited as long as the target reaction proceeds, and may include water solvent, ether solvents such as diethyl ether, diisopropyl ether, methyl-t-butyl ether, dimethoxyethane, tetrahydrofuran and dioxane, benzene based solvents such as benzene, toluene, xylene, mesitylene, chlorobenzene and dichlorobenzene, and the like. These solvents may be used singly, or two or more kinds may be used in combination in an optional ratio.

(585) An amount of the solvent to be used in the present reaction is not particularly limited as long as the target reaction proceeds, and is usually 3 times by weight or more and 200 times by weight or less relative to the compound represented by Formula (1a-b).

(586) A temperature to carry out the present reaction is not particularly limited as long as the target reaction proceeds, and is usually 30° C. or higher and 200° C. or lower or a boiling point of the solvent or lower.

(587) As a post treatment after the reaction, it is possible to carry out a liquid separating operation by adding water or a suitable aqueous solution to the reaction mixture. When an aqueous solution is to be used, an acidic aqueous solution in which hydrochloric acid, sulfuric acid, ammonium chloride or the like is dissolved, an alkaline aqueous solution in which potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate or the like is dissolved or a saline solution or the like can be optionally used. At the time of the liquid separating operation, if necessary, it is possible to add a solvent which is immiscible with water including benzene based solvents such as toluene, xylene, benzene, chlorobenzene and dichlorobenzene, ester solvents such as ethyl acetate, isopropyl acetate and butyl acetate, ether solvents such as diethyl ether, diisopropyl ether and methyl-t-butyl ether, halogen based solvents such as dichloromethane, dichloroethane, chloroform and carbon tetrachloride, hydrocarbon solvents such as hexane, heptane, cyclohexane and methylcyclohexane, and the like. In addition, it is possible to use these solvents singly or to mix two or more kinds with an optional ratio. The number of times of the liquid separation is not particularly limited, and may be carried out in accordance with the purity and yield to be desired. In addition, it is also possible to remove insoluble materials by subjecting to filtration operation but it is not essential.

(588) The reaction mixture obtained above which contains the compound represented by Formula (1a-d) may be dehydrated with a drying agent such as sodium sulfate and magnesium sulfate, but this is not essential.

(589) The reaction mixture obtained above which contains the compound represented by Formula (1a-d) may be distilled under reduced pressure to remove the solvent as long as the compound is not decomposed.

(590) The reaction mixture obtained after distillation of the solvent which contains the compound represented by Formula (1a-d) may be purified by washing, reprecipitation, recrystallization, column chromatography and the like, using a suitable solvent. It may be optionally set in accordance with the desired purity.

(591) [Production Method I]

(592) ##STR03486##

(593) In the formula, R2e represents a C2-C6 alkynyl group optionally substituted with substituent(s) A or a C2-C6 haloalkynyl group, and R1, Het, R2b, X and Y are the same as defined hereinabove.

(594) Production Method I is a synthetic method of a compound represented by Formula (1a-e), among the compounds represented by Formula (1a), wherein R2e is a C2-C6 alkynyl group optionally substituted with substituent(s) A or a C2-C6 haloalkynyl group, and is a production method which comprises Sonogashira coupling wherein a compound represented by (1a-b) and a terminal-alkyne compound are reacted in the presence of a transition metal and a base in a solvent.

(595) In Formula (1a-b), preferable R2b is a chlorine atom, a bromine atom or an iodine atom.

(596) The terminal-alkyne compound to be used in the present reaction can be obtained as a commercially available product or produced by a conventionally known method. In addition, as the terminal-alkyne compound, trimethylsilylacetylene may be also used. In such a case, after introducing trimethylsilylethynyl group into the compound represented by Formula (1a-b), desilylation is required to be carried out.

(597) With regard to the desilylation, it may be carried out with reference to Non-Patent Documents such as Journal of the American Chemical Society, vol. 131, No. 2, pp. 634-643 (2009) and Journal of Organometallic Chemistry, vol. 696, No. 25, pp. 4039-4045 (2011).

(598) An amount of the terminal-alkyne compound to be used in the present reaction may be 1 equivalent or more relative to the compound represented by Formula (1a-b), which is not particularly limited as long as the target reaction proceeds, and preferably 1 equivalent or more and 10 equivalents or less.

(599) The transition metal to be used in the present reaction may have a ligand, and may include palladiums such as palladium acetate, [1,1′-bis(diphenyl-phosphine)ferrocene]palladium dichloride, tris(dibenzylideneacetone)dipalladium, tetrakis(triphenylphosphine)palladium, bis(triphenylphosphine)palladium dichloride and the like. In addition, coppers such as copper chloride, copper bromide, copper iodate and the like may also be used simultaneously.

(600) With regard to an amount of the transition metal to be used in the present reaction, palladiums and coppers each may be used in 0.001 equivalent or more relative to the compound represented by Formula (1a-b), and is not particularly limited as long as the target reaction proceeds. Preferable amounts thereof are each 0.001 equivalent or more and 1 equivalent or less.

(601) The base to be used in the present reaction may include organic amines such as triethylamine, tributylamine, isopropylamine, diethylamine, diisopropylamine and diisopropylethylamine, inorganic bases such as sodium carbonate, potassium carbonate and cesium carbonate and the like.

(602) An amount of the base to be used in the present reaction may be 1 equivalent or more relative to the compound represented by Formula (1a-b), which is not particularly limited as long as the target reaction proceeds, and preferably 1 equivalent or more and 50 equivalents or less. In addition, the organic bases which is in a liquid state can be also used as a solvent.

(603) In order to proceed the reaction efficiently, a phosphine ligand such as tri-t-butyl phosphine, 2-dicyclohexylphosphino-2′4′6′-triisopropylbiphenyl and the like may be added, but this is not essential.

(604) An amount of the phosphine ligand to be used in the present reaction may be 0.001 equivalent or more and 1 equivalent or less relative to the compound represented by Formula (1a-b), and is not particularly limited as long as the target reaction proceeds.

(605) The solvent to be used in the present reaction is not particularly limited as long as the target reaction proceeds, and may include ether solvents such as diethyl ether, diisopropyl ether, methyl-t-butyl ether, dimethoxyethane, tetrahydrofuran and dioxane, benzene based solvents such as benzene, toluene, xylene, mesitylene, chlorobenzene and dichlorobenzene, ester solvents such as ethyl acetate, isopropyl acetate and butyl acetate, nitrile solvents such as acetonitrile, amide solvents such as N-methylpyrrolidone, N,N-dimethylformamide and N,N-dimethylacetamide, urea solvents such as 1,3-dimethyl-2-imidazolidinone, halogen based solvents such as dichloromethane, dichloroethane, chloroform and carbon tetrachloride, an organic amine solvent such as triethylamine, tributylamine, isopropylamine, diethylamine, diisopropylamine and diisopropylethylamine, and the like. These solvents may be used singly, or two or more kinds may be used in combination in an optional ratio.

(606) An amount of the solvent to be used in the present reaction is not particularly limited as long as the target reaction proceeds, and is usually 3 times by weight or more and 200 times by weight or less relative to the compound represented by Formula (1a-b).

(607) A temperature to carry out the present reaction is not particularly limited as long as the target reaction proceeds, and is usually 0° C. or higher and 150° C. or lower or a boiling point of the solvent or lower.

(608) As a post treatment after the reaction, it is possible to carry out a liquid separating operation by adding water or a suitable aqueous solution to the reaction mixture. When an aqueous solution is to be used, an acidic aqueous solution in which hydrochloric acid, sulfuric acid or the like is dissolved, an alkaline aqueous solution in which potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate or the like is dissolved or a saline solution or the like can be optionally used. At the time of the liquid separating operation, if necessary, it is possible to add a solvent which is immiscible with water including benzene based solvents such as toluene, xylene, benzene, chlorobenzene and dichlorobenzene, ester solvents such as ethyl acetate, isopropyl acetate and butyl acetate, ether solvents such as diethyl ether, diisopropyl ether and methyl-t-butyl ether, halogen based solvents such as dichloromethane, dichloroethane, chloroform and carbon tetrachloride, hydrocarbon solvents such as hexane, heptane, cyclohexane and methylcyclohexane, and the like. In addition, it is possible to use these solvents singly or to mix two or more kinds with an optional ratio. The number of times of the liquid separation is not particularly limited, and may be carried out in accordance with the purity and yield to be desired. In addition, it is also possible to remove insoluble materials by subjecting to filtration operation but it is not essential.

(609) The reaction mixture obtained above which contains the compound represented by Formula (1a-e) may be dehydrated with a drying agent such as sodium sulfate and magnesium sulfate, but this is not essential.

(610) The reaction mixture obtained above which contains the compound represented by Formula (1a-e) may be distilled under reduced pressure to remove the solvent as long as the compound is not decomposed.

(611) The reaction mixture obtained after distillation of the solvent which contains the compound represented by Formula (1a-e) may be purified by washing, reprecipitation, recrystallization, column chromatography and the like, using a suitable solvent. It may be optionally set in accordance with the desired purity.

(612) [Production Method J]

(613) ##STR03487##

(614) In the formula, Rya represents a C1-C6 alkoxy group, Het1 represents a 5 to 6-membered heterocyclic group or the 8 to 10-membered heterocyclic group, the 5 to 6-membered heterocyclic group or the 8 to 10-membered heterocyclic group is optionally substituted with 0 to 5 substituents R3 (with the proviso that when two or more substituents R3 are present, each R3 represents an independent substituent), and R1, R2, X, Y and the broken line are the same as defined hereinabove.

(615) Production Method J is a synthetic method of a compound represented by Formula (1-b) having a hydroxyl group which belongs to the compounds represented by Formula (1), and is a production method which comprises reacting a compound represented by Formula (1-a) wherein Rya is a C1-C6 alkoxy group and an acid in a solvent.

(616) The acid to be used in the present reaction may include boron halides such as boron trichloride and boron tribromide.

(617) An amount of the acid to be used in the present reaction may be 1 equivalent or more relative to the compound represented by Formula (1-a), which is not particularly limited as long as the target reaction proceeds, and preferably 1 equivalent or more and 10 equivalents or less.

(618) The solvent to be used in the present reaction is not particularly limited as long as the target reaction proceeds, and may include benzene based solvents such as benzene, toluene, xylene, mesitylene, chlorobenzene and dichlorobenzene, nitrile solvents such as acetonitrile, halogen based solvents such as dichloromethane, dichloroethane, chloroform and carbon tetrachloride, hydrocarbon solvents such as hexane, heptane, cyclohexane and methylcyclohexane, and the like. These solvents may be used singly, or two or more kinds may be used in combination in an optional ratio.

(619) An amount of the solvent to be used in the present reaction is not particularly limited as long as the target reaction proceeds, and is usually 3 times by weight or more and 200 times by weight or less relative to the compound represented by Formula (1-a).

(620) A temperature to carry out the present reaction is not particularly limited as long as the target reaction proceeds, and is usually −80° C. or higher and 100° C. or lower or a boiling point of the solvent or lower.

(621) As a post treatment after the reaction, it is possible to carry out a liquid separating operation by adding water or a suitable aqueous solution to the reaction mixture. When an aqueous solution is to be used, an acidic aqueous solution in which hydrochloric acid, sulfuric acid, ammonium chloride or the like is dissolved, an alkaline aqueous solution in which potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate or the like is dissolved or a saline solution or the like can be optionally used. At the time of the liquid separating operation, if necessary, it is possible to add a solvent which is immiscible with water including benzene based solvents such as toluene, xylene, benzene, chlorobenzene and dichlorobenzene, ester solvents such as ethyl acetate, isopropyl acetate and butyl acetate, ether solvents such as diethyl ether, diisopropyl ether and methyl-t-butyl ether, halogen based solvents such as dichloromethane, dichloroethane, chloroform and carbon tetrachloride, hydrocarbon solvents such as hexane, heptane, cyclohexane and methylcyclohexane, and the like. In addition, it is possible to use these solvents singly or to mix two or more kinds with an optional ratio. The number of times of the liquid separation is not particularly limited, and may be carried out in accordance with the purity and yield to be desired.

(622) The reaction mixture obtained above which contains the compound represented by Formula (1-b) may be dehydrated with a drying agent such as sodium sulfate and magnesium sulfate, but this is not essential.

(623) The reaction mixture obtained above which contains the compound represented by Formula (1-b) may be distilled under reduced pressure to remove the solvent as long as the compound is not decomposed.

(624) The reaction mixture obtained after distillation of the solvent which contains the compound represented by Formula (1-b) may be purified by washing, reprecipitation, recrystallization, column chromatography and the like, using a suitable solvent. It may be optionally set in accordance with the desired purity.

(625) [Production Method K]

(626) ##STR03488##

(627) In the formula, Ryb represents a C1-C6 alkyl group optionally substituted with substituent(s) C, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group optionally substituted with substituent(s) C, a C2-C6 alkenyl group optionally substituted with substituent(s) C, a C2-C6 haloalkenyl group, a C3-C6 alkynyl group optionally substituted with substituent(s) C, a C3-C6 haloalkynyl group, an aryl group optionally substituted with substituent(s) D, a heteroaryl group optionally substituted with substituent(s) D, an aralkyl group optionally substituted with substituent(s) D or Rx1C(═O)—, and Lv, R1, R2, Het1, Rx1, X, Y and the broken line are the same as defined hereinabove.

(628) Production Method K is a synthetic method of a compound represented by Formula (1-c), which belongs to the compounds represented by Formula (1), wherein Ryb-O— represents a C1-C6 alkoxy group optionally substituted with substituent(s) C, a C1-C6 haloalkoxy group, a C3-C8 cycloalkoxy group optionally substituted with substituent(s) C, a C2-C6 alkenyloxy group optionally substituted with substituent(s) C, a C2-C6 haloalkenyloxy group, a C3-C6 alkynyloxy group optionally substituted with substituent(s) C, a C3-C6 haloalkynyloxy group, an aryloxy group optionally substituted with substituent(s) D, a heteroaryloxy group optionally substituted with substituent(s) D, an aralkyloxy group optionally substituted with substituent(s) D or Rx1C(═O)O— (Rx1 is the same as defined hereinabove), and is a production method which comprises reacting a compounds represented by Formula (1-b) and Ryb-Lv in the presence of a base in a solvent.

(629) The Ryb-Lv to be used in the present reaction can be obtained as a commercially available product or produced by a conventionally known method.

(630) The Ryb-Lv to be used in the present reaction may be 1 equivalent or more relative to the compounds represented by Formula (i-b), which is not particularly limited as long as the target reaction proceeds, and preferably 1 equivalent or more and 10 equivalents or less.

(631) The base to be used in the present reaction may be exemplified by inorganic bases such as sodium carbonate, potassium carbonate, cesium carbonate and sodium hydride, and organic bases such as triethylamine, tributylamine, diisopropylethylamine, pyridine, 4-dimethylaminopyridine, collidine and lutidine, and is not particularly limited as long as the target reaction proceeds.

(632) The base to be used in the present reaction may be 1 equivalent or more relative to the compound represented by Formula (1-b), which is not particularly limited as long as the target reaction proceeds, and preferably 1 equivalent or more and 10 equivalents or less.

(633) The solvent to be used in the present reaction is not particularly limited as long as the target reaction proceeds, and may include ether solvents such as diethyl ether, diisopropyl ether, methyl-t-butyl ether, dimethoxyethane, tetrahydrofuran and dioxane, alcohol solvents such as methanol, ethanol and isopropanol, benzene based solvents such as benzene, toluene, xylene, mesitylene, chlorobenzene and dichlorobenzene, ester solvents such as ethyl acetate, isopropyl acetate and butyl acetate, nitrile solvents such as acetonitrile, amide solvents such as N-methylpyrrolidone, N,N-dimethylformamide and N,N-dimethylacetamide, urea solvents such as 1,3-dimethyl-2-imidazolidinone, halogen based solvents such as dichloromethane, dichloroethane, chloroform and carbon tetrachloride, sulfur solvents such as dimethylsulfoxide and sulforane, ketone solvents such as acetone, methyl ethyl ketone and methyl isobutyl ketone, and the like. These solvents may be used singly, or two or more kinds may be used in combination in an optional ratio.

(634) An amount of the solvent to be used in the present reaction is not particularly limited as long as the target reaction proceeds, and is usually 3 times by weight or more and 200 times by weight or less relative to the compound represented by Formula (1-b).

(635) A temperature to carry out the present reaction is not particularly limited as long as the target reaction proceeds, and is usually −20° C. or higher and 150° C. or lower or a boiling point of the solvent or lower.

(636) As a post treatment after the reaction, it is possible to carry out a liquid separating operation by adding water or a suitable aqueous solution to the reaction mixture. When an aqueous solution is to be used, an acidic aqueous solution in which hydrochloric acid, sulfuric acid, ammonium chloride or the like is dissolved, an alkaline aqueous solution in which potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate or the like is dissolved, an aqueous solution in which a salt containing a sulfur atom such as sodium thiosulfate, sodium sulfite or the like is dissolved or a saline solution or the like can be optionally used. At the time of the liquid separating operation, if necessary, it is possible to add a solvent which is immiscible with water including benzene based solvents such as toluene, xylene, benzene, chlorobenzene and dichlorobenzene, ester solvents such as ethyl acetate, isopropyl acetate and butyl acetate, ether solvents such as diethyl ether, diisopropyl ether and methyl-t-butyl ether, halogen based solvents such as dichloromethane, dichloroethane, chloroform and carbon tetrachloride, hydrocarbon solvents such as hexane, heptane, cyclohexane and methylcyclohexane, and the like. In addition, it is possible to use these solvents singly or to mix two or more kinds with an optional ratio. The number of times of the liquid separation is not particularly limited, and may be carried out in accordance with the purity and yield to be desired.

(637) The reaction mixture obtained above which contains the compound represented by Formula (1-c) may be dehydrated with a drying agent such as sodium sulfate and magnesium sulfate, but this is not essential.

(638) The reaction mixture obtained above which contains the compound represented by Formula (1-c) may be distilled under reduced pressure to remove the solvent as long as the compound is not decomposed.

(639) The reaction mixture obtained after distillation of the solvent which contains the compound represented by Formula (1-c) may be purified by washing, reprecipitation, recrystallization, column chromatography and the like, using a suitable solvent. It may be optionally set in accordance with the desired purity.

(640) [Production Method L].

(641) ##STR03489##

(642) In the formula, Ya represents a phenyl group, a pyridyl group, a pyridazinyl group, a pyrimidinyl group, a pyrazinyl group, a triazinyl group, a tetrazinyl group, a thienyl group, a thiazolyl group, an isothiazolyl group or a thiadiazolyl group, wherein when the phenyl group is substituted with the Rya at the ortho-position, the group is further optionally substituted with 0 to 4 substituents R5 (with the proviso that when two or more substituents R5 are present, each R5 represents an independent substituent), and when R4 is positioned at the ortho-position, the group is further optionally substituted with 0 to 3 substituents R5 (with the proviso that when two or more substituents R5 are present, each R5 represents an independent substituent), and when the pyridyl group, the pyrazinyl group, the pyrimidinyl group, the pyridazinyl group, the a triazinyl group or the tetrazinyl group is substituted with the Rya at the ortho-position, the group is further optionally substituted with 0 to 3 substituents R5 (with the proviso that when two or more substituents R5 are present, each R5 represents an independent substituent), and when R4 is positioned at the ortho-position, the group is further optionally substituted with 0 to 2 substituents R5 (with the proviso that when two substituents R5 are present, each R5 represents an independent substituent), and R1, R2, Rya, X, Het and the broken line are the same as defined hereinabove.

(643) Production Method L is a synthetic method of a compound represented by Formula (1-e) having a hydroxyl group at Y which belongs to the compounds represented by Formula (1), and is a production method which comprises reacting a compound represented by Formula (1-d) and an acid in a solvent.

(644) By using the compound represented by Formula (1-d) in place of the compound represented by Formula (1-a) in Production Method J, Production Method L can be carried out in accordance with Production Method J.

(645) [Production Method M]

(646) ##STR03490##

(647) In the formula, Yb represents a phenyl group, a pyridyl group, a pyridazinyl group, a pyrimidinyl group, a pyrazinyl group, a triazinyl group, a tetrazinyl group, a thienyl group, a thiazolyl group, an isothiazolyl group or a thiadiazolyl group, wherein when the phenyl group is substituted with a hydroxyl group at the ortho-position, the group is further optionally substituted with 0 to 4 substituents R5 (with the proviso that when two or more substituents R5 are present, each R5 represents an independent substituent), and when R4 is positioned at the ortho-position, the group is further optionally substituted with 0 to 3 substituents R5 (with the proviso that when two or more substituents R5 are present, each R5 represents an independent substituent), and when the pyridyl group, the pyrazinyl group, the pyrimidinyl group, the pyridazinyl group, the a triazinyl group or the tetrazinyl group is substituted with hydroxyl group at the ortho-position, the group is further optionally substituted with 0 to 3 substituents R5 (with the proviso that when two or more substituents R5 are present, each R5 represents an independent substituent), and when R4 is positioned at the ortho-position, the group is further optionally substituted with 0 to 2 substituents R5 (with the proviso that when two substituents R5 are present, each R5 represents an independent substituent), and Lv, R1, R2, Het, Ryb, X and the broken line are the same as defined hereinabove. The hydroxyl group in the compound represented by Formula (1-e) and the Ryb-O— in the compound represented by Formula (1-f) represent a substituent corresponding to either of R4 or R5, or each other's substituents.

(648) Production Method M is a synthetic method of a compound represented by Formula (1-f) which belongs to the compounds represented by Formula (1), and is a production method which comprises reacting a compound represented by Formula (1-e) and Ryb-Lv in the presence of a base in a solvent.

(649) By using the compound represented by Formula (1-e) in place of the compound represented by Formula (1-b) in Production Method K, Production Method M can be carried out in accordance with Production Method K.

(650) [Production Method N]

(651) ##STR03491##

(652) In the formula, Ryc represents a halogen atom, Ryd represents a C1-C6 alkyl group optionally substituted with substituent(s) C, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group optionally substituted with substituent(s) C, a C2-C6 alkenyl group optionally substituted with substituent(s) C, a C2-C6 haloalkenyl group, an aryl group optionally substituted with substituent(s) D or a heteroaryl group optionally substituted with substituent(s) D, Het2 represents a 5 to 6-membered heterocyclic group or a 8 to 10-membered heterocyclic group, the 5 to 6-membered heterocyclic group or the 8 to 10-membered heterocyclic group is optionally substituted with 0 to 5 substituents R3 (with the proviso that when two or more substituents R3 are present, each R3 represents an independent substituent), Ryd-B represents an organic boronic acid, and R1, R2, X, Y and the broken line are the same as defined hereinabove.

(653) Production Method N is a synthetic method of a compound represented by Formula (1-h), which belongs to the compounds represented by Formula (1), wherein Ryd is a C1-C6 alkyl group optionally substituted with substituent(s) C, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group optionally substituted with substituent(s) C, a C2-C6 alkenyl group optionally substituted with substituent(s) C, a C2-C6 haloalkenyl group, an aryl group optionally substituted with substituent(s) D or a heteroaryl group optionally substituted with substituent(s) D, and is a production method which comprises Suzuki-Miyaura coupling wherein a compound represented by Formula (1-g) and an organic boronic acid (Ryd-B) are reacted in the presence of a transition metal and a base in a solvent.

(654) In the compound represented by Formula (1-g), preferable Ryc is a chlorine atom, a bromine atom or an iodine atom.

(655) The Ryd-B to be used in the present reaction represents organic boronic acids such as an organic boronic acid and an organic boronic acid ester, and can be obtained as a commercially available product or produced by a conventionally known method.

(656) By using the compound represented by Formula (1-g) and Ryd-B in place of the compound represented by Formula (1a-b) and R2d-B in Production Method H, respectively, Production Method N can be carried out in accordance with Production Method H.

(657) [Production Method O]

(658) ##STR03492##

(659) In the formula, Yc represents a phenyl group, a pyridyl group, a pyridazinyl group, a pyrimidinyl group, a pyrazinyl group, a triazinyl group, a tetrazinyl group, a thienyl group, a thiazolyl group, an isothiazolyl group or a thiadiazolyl group, wherein when the phenyl group is substituted with Ryc at the ortho-position, the group is further optionally substituted with 0 to 4 substituents R5 (with the proviso that when two or more substituents R5 are present, each R5 represents an independent substituent), and when R4 is positioned at the ortho-position, the group is further optionally substituted with 0 to 3 substituents R5 (with the proviso that when two or more substituents R5 are present, each R5 represents an independent substituent), and when the pyridyl group, the pyrazinyl group, the pyrimidinyl group, the pyridazinyl group, the a triazinyl group or the tetrazinyl group is substituted with Ryc at the ortho-position, the group is further optionally substituted with 0 to 3 substituents R5 (with the proviso that when two or more substituents R5 are present, each R5 represents an independent substituent), and when R4 is positioned at the ortho-position, the group is further optionally substituted with 0 to 2 substituents R5 (with the proviso that when two substituents R5 are present, each R5 represents an independent substituent), and Ryc, Ryd, Ryd-B, R1, R2, X, Het and the broken line are the same as defined hereinabove. The Ryc in the compound represented by Formula (1-i) and the Ryd in the compound represented by Formula (1-j) represent a substituent corresponding to either of R4 or R5, or each other's substituents.

(660) Production Method O is a synthetic method of a compound represented by Formula (1-j) which belongs to the compounds represented by Formula (1), and is a production method which comprises Suzuki-Miyaura coupling wherein a compound represented by Formula (1-i) and an organic boronic acid (Ryd-B) are reacted in the presence of a transition metal and a base in a solvent.

(661) In the compounds represented by Formula (1-i), preferable Ryc is a chlorine atom, a bromine atom or an iodine atom.

(662) By using the compound represented by Formula (1-i) and Ryd-B in place of the compound represented by Formula (1a-b) and R2d-B in Production Method H, respectively, Production Method O can be carried out in accordance with Production Method H.

(663) [Production Method P]

(664) ##STR03493##

(665) In the formula, Rye represents a C2-C6 alkynyl group optionally substituted with substituent(s) C or a C2-C6 haloalkynyl group, and Ryc, R1, R2, X, Y, Het2 and the broken line are the same as defined hereinabove.

(666) Production Method P is a synthetic method of a compound represented by Formula (1-k), which belongs to the compounds represented by Formula (1), wherein Rye is a C2-C6 alkynyl group optionally substituted with substituent(s) C or a C2-C6 haloalkynyl group, and is a production method which comprises Sonogashira coupling wherein a compound represented by Formula (1-g) and a terminal-alkyne compound are reacted in the presence of a transition metal and a base in a solvent.

(667) Among the compounds represented by Formula (1-g), preferable Ryc is a chlorine atom, a bromine atom or an iodine atom.

(668) By using the compound represented by Formula (1-g) in place of the compound represented by Formula (1a-b) in Production Method I, Production Method P can be carried out in accordance with Production Method I.

(669) [Production Method Q]

(670) ##STR03494##

(671) In the formula, Ryc, Rye, R1, R2, X, Yc, Het and the broken line are the same as defined hereinabove. The Ryc in the compound represented by Formula (1-i) and the Rye in the compound represented by Formula (1-1) represent a substituent corresponding to either of R4 or R5, or each other's substituents.

(672) Production Method Q is a synthetic method of a compound represented by Formula (1-1) which belongs to the compounds represented by Formula (1), and is a production method which comprises Sonogashira coupling wherein a compound represented by Formula (1-i) and a terminal-alkyne compound are reacted in the presence of a transition metal and a base in a solvent.

(673) In the compound represented by Formula (1-i), preferable Ryc is a chlorine atom, a bromine atom or an iodine atom.

(674) By using the compound represented by Formula (1-i) in place of the compound represented by Formula (1a-b) in Production Method I, Production Method Q can be carried out in accordance with Production Method I.

(675) [Production Method R]

(676) ##STR03495##

(677) In the formula, Ryf represents a halogen atom, Het3 represents a 5 to 6-membered heterocyclic group or a 8 to 10-membered heterocyclic group, the 5 to 6-membered heterocyclic group or the 8 to 10-membered heterocyclic group is optionally substituted with 0 to 5 substituents R3 (with the proviso that when two or more substituents R3 are present, each R3 represents an independent substituent), and HalR, R1, R2, X, Y and the broken line are the same as defined hereinabove.

(678) Production Method R is a production method of a compound represented by Formula (1-n), which belongs to the compounds represented by Formula (1), wherein Ryf is a halogen atom, and is a production method which comprises reacting a compound represented by Formula (1-m) and a halogenating agent (HalR) in a solvent.

(679) A base or a radical initiator may be added to the present reaction. It may be optionally set so that the target reaction proceeds.

(680) In the following, a method of reacting a compound represented by Formula (1-m) and a halogenating agent (HalR) in a solvent will be described.

(681) The halogenating agent to be used in the present reaction may include Selectfluor (N-fluoro-N′-triethylenediamine bis(tetrafluoroborate)), N-chlorosuccinimide, N-bromosuccinimide, N-iodosuccinimide, 1,3-dichloro-5,5-dimethylhydantoin, 1,3-dibromo-5,5-dimethylhydantoin, 1,3-diiodo-5,5-dimethylhydantoin, bromine, iodine and the like,

(682) An amount of the halogenating agent to be used in the present reaction may be 1 equivalent or more relative to the compound represented by Formula (1-m), which is not particularly limited as long as the target reaction proceeds, and preferably 1 equivalent or more and 10 equivalents or less. If the amount of the halogenating agent including hydantoin is 0.5 equivalent or more, it is not particularly limited as long as the target reaction proceeds, and preferably 1 equivalent or more and 5 equivalents or less.

(683) When the halogenating agent to be used in the present reaction is an iodinating agent, an acid including an inorganic acid such as hydrochloric acid, sulfuric acid or the like, or an organic acid such as acetic acid, trifluoroacetic acid, methanesulfonic acid, trifluoromethanesulfonic acid or the like may be added.

(684) An amount of the acid to be used when the halogenating agent to be used in the present reaction is the iodinating agent may be 0.01 equivalent or more relative to the compound represented by Formula (1-m), which is not particularly limited as long as the target reaction proceeds, and preferably 0.1 equivalent or more and 3 equivalents or less.

(685) The solvent to be used in the present reaction is not particularly limited as long as the target reaction proceeds, and may include acidic solvents such as sulfuric acid, acetic acid, trifluoroacetic acid, methanesulfonic acid and trifluoromethanesulfonic acid, ether solvents such as diethyl ether, diisopropyl ether, methyl-t-butyl ether, dimethoxyethane, tetrahydrofuran and dioxane, alcohol solvents such as methanol, ethanol and isopropanol, benzene based solvents such as benzene, toluene, xylene, mesitylene, chlorobenzene and dichlorobenzene, ester solvents such as ethyl acetate, isopropyl acetate and butyl acetate, nitrile solvents such as acetonitrile, amide solvents such as N-methylpyrrolidone, N,N-dimethylformamide and N,N-dimethylacetamide, urea solvents such as 1,3-dimethyl-2-imidazolidinone, halogen based solvents such as dichloromethane, dichloroethane, chloroform and carbon tetrachloride, and the like.

(686) These solvents may be used singly, or two or more kinds may be used in combination in an optional ratio.

(687) An amount of the solvent to be used in the present reaction is not particularly limited as long as the target reaction proceeds, and is usually 3 times by weight or more and 200 times by weight or less relative to the compound represented by Formula (1-m).

(688) A temperature to carry out the present reaction is not particularly limited as long as the target reaction proceeds, and is usually 0° C. or higher and 150° C. or lower or a boiling point of the solvent or lower.

(689) As a post treatment after the reaction, it is possible to carry out a liquid separating operation by adding water or a suitable aqueous solution to the reaction mixture. When an aqueous solution is to be used, an acidic aqueous solution in which hydrochloric acid, sulfuric acid, ammonium chloride or the like is dissolved, an alkaline aqueous solution in which potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate or the like is dissolved, an aqueous solution in which a salt containing a sulfur atom such as sodium thiosulfate, sodium sulfite or the like is dissolved or a saline solution or the like can be optionally used. At the time of the liquid separating operation, if necessary, it is possible to add a solvent which is immiscible with water including benzene based solvents such as toluene, xylene, benzene, chlorobenzene and dichlorobenzene, ester solvents such as ethyl acetate, isopropyl acetate and butyl acetate, ether solvents such as diethyl ether, diisopropyl ether and methyl-t-butyl ether, halogen based solvents such as dichloromethane, dichloroethane, chloroform and carbon tetrachloride, hydrocarbon solvents such as hexane, heptane, cyclohexane and methylcyclohexane, and the like. In addition, it is possible to use these solvents singly or to mix two or more kinds with an optional ratio. The number of times of the liquid separation is not particularly limited, and may be carried out in accordance with the purity and yield to be desired.

(690) The reaction mixture obtained above which contains the compound represented by Formula (1-n) may be dehydrated with a drying agent such as sodium sulfate and magnesium sulfate, but this is not essential.

(691) The reaction mixture obtained above which contains the compound represented by Formula (1-n) may be distilled under reduced pressure to remove the solvent as long as the compound is not decomposed.

(692) The reaction mixture obtained after distillation of the solvent which contains the compound represented by Formula (1-n) may be purified by washing, reprecipitation, recrystallization, column chromatography and the like, using a suitable solvent. It may be optionally set in accordance with the desired purity.

(693) In the following, a method of reacting a compound represented by Formula (1-m) and a halogenating agent (HalR) in the presence of a base in a solvent will be described.

(694) The halogenating agent to be used in the present reaction may include Selectfluor (N-fluoro-N′-triethylenediamine bis(tetrafluoroborate)), N-chlorosuccinimide, N-bromosuccinimide, N-iodosuccinimide, 1,3-dichloro-5,5-dimethylhydantoin, 1,3-dibromo-5,5-dimethylhydantoin, 1,3-diiodo-5,5-dimethylhydantoin, hexachloro-ethane, bromine, iodine and the like.

(695) An amount of the halogenating agent to be used in the present reaction may be 1 equivalent or more relative to the compound represented by Formula (1-m), which is not particularly limited as long as the target reaction proceeds, and preferably 1 equivalent or more and 10 equivalents or less. If the amount of the halogenating agent including hydantoin is 0.5 equivalent or more, it is not particularly limited as long as the target reaction proceeds, and preferably 1 equivalent or more and 5 equivalents or less.

(696) The base to be used in the present reaction may be exemplified by metal hydrides such as sodium hydride, organolithiums such as methyllithium, butyllithium, sec-butyllithium, t-butyllithium and hexyllithium, metal amides such as lithium diisopropylamide, hexamethyldisilazane lithium, hexamethyldisilazane sodium and hexamethyldisilazane potassium, and it is not particularly limited as long as the target reaction proceeds.

(697) An amount of the base to be used in the present reaction may be 1 equivalent or more relative to the compound represented by Formula (1-m), which is not particularly limited as long as the target reaction proceeds, and preferably 1 equivalent or more and 10 equivalents or less.

(698) The solvent to be used in the present reaction is not particularly limited as long as the target reaction proceeds, and may include ether solvents such as diethyl ether, diisopropyl ether, methyl-t-butyl ether, dimethoxyethane, tetrahydrofuran and dioxane, amide solvents such as N-methylpyrrolidone, N,N-dimethylformamide and N,N-dimethylacetamide, urea solvents such as 1,3-dimethyl-2-imidazolidinone, benzene based solvents such as benzene, toluene, xylene, mesitylene, chlorobenzene and dichlorobenzene, and the like. These solvents may be used singly, or two or more kinds may be used in combination in an optional ratio.

(699) An amount of the solvent to be used in the present reaction is not particularly limited as long as the target reaction proceeds, and is usually 3 times by weight or more and 200 times by weight or less relative to the compound represented by Formula (1-m).

(700) A temperature to carry out the present reaction is not particularly limited as long as the target reaction proceeds, and is usually −80° C. or higher and 100° C. or lower or a boiling point of the solvent or lower.

(701) As a post treatment after the reaction, it is possible to carry out a liquid separating operation by adding water or a suitable aqueous solution to the reaction mixture. When an aqueous solution is to be used, an acidic aqueous solution in which hydrochloric acid, sulfuric acid, ammonium chloride or the like is dissolved, an alkaline aqueous solution in which potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate or the like is dissolved, an aqueous solution in which a salt containing a sulfur, atom such as sodium thiosulfate, sodium sulfite or the like is dissolved or a saline solution or the like can be optionally used. At the time of the liquid separating operation, if necessary, it is possible to add a solvent which is immiscible with water including benzene based solvents such as toluene, xylene, benzene, chlorobenzene and dichlorobenzene, ester solvents such as ethyl acetate, isopropyl acetate and butyl acetate, ether solvents such as diethyl ether, diisopropyl ether and methyl-t-butyl ether, halogen based solvents such as dichloromethane, dichloroethane and chloroform, hydrocarbon solvents such as hexane, heptane, cyclohexane and methylcyclohexane, and the like. In addition, it is possible to use these solvents singly or to mix two or more kinds with an optional ratio. The number of times of the liquid separation is not particularly limited, and may be carried out in accordance with the purity and yield to be desired.

(702) The reaction mixture obtained above which contains the compound represented by Formula (1-n) may be dehydrated with a drying agent such as sodium sulfate and magnesium sulfate, but this is not essential.

(703) The reaction mixture obtained above which contains the compound represented by Formula (1-n) may be distilled under reduced pressure to remove the solvent as long as the compound is not decomposed.

(704) The reaction mixture obtained after distillation of the solvent which contains the compound represented by Formula (1-n) may be purified by washing, reprecipitation, recrystallization, column chromatography and the like, using a suitable solvent. It may be optionally set in accordance with the desired purity.

(705) In the following, a method of reacting a compound represented by Formula (1-m), a halogenating agent (HalR) and a radical initiator in a solvent will be described.

(706) The radical initiator to be used in the present reaction may include azobisisobutyronitrile, 2,2′-azobis(4-methoxy-2,4-dimethylvaleryonitrile), benzoyl peroxide and the like.

(707) An amount of the radical initiator to be used in the present reaction is not particularly limited as long as the target reaction proceeds, and is usually 0.01 equivalent or more and 1.0 equivalent or less relative to the compound represented by Formula (1-m).

(708) The halogenating agent to be used in the present reaction may include N-chlorosuccinimide, N-bromosuccinimide, N-iodosuccinimide, 1,3-dichloro-5,5-dimethylhydantoin, 1,3-dibromo-5,5-dimethylhydantoin, 1,3-diiodo-5,5-dimethylhydantoin and the like.

(709) An amount of the halogenating agent to be used in the present reaction may be 1 equivalent or more relative to the compound represented by Formula (1-m), which is not particularly limited as long as the target reaction proceeds, and is usually 1 equivalent or more and 1.8 equivalents or less.

(710) The solvent to be used in the present reaction is not particularly limited as long as the target reaction proceeds, and may include halogenated benzene solvents such as chlorobenzene and dichlorobenzene, ester solvents such as ethyl acetate, isopropyl acetate and butyl acetate, halogen based solvents such as dichloromethane, dichloroethane, chloroform and carbon tetrachloride, hydrocarbon solvents such as hexane, heptane, cyclohexane and methylcyclohexane, and the like. These solvents may be used singly, or two or more kinds may be used in combination in an optional ratio.

(711) An amount of the solvent to be used in the present reaction is not particularly limited as long as the target reaction proceeds, and is usually 3 times by weight or more and 200 times by weight or less relative to the compound represented by Formula (1-m).

(712) A temperature to carry out the present reaction is not particularly limited as long as the target reaction proceeds, and is usually 20° C. or higher and 150° C. or lower or a boiling point of the solvent or lower.

(713) As a post treatment after the reaction, it is possible to carry out a liquid separating operation by adding water or a suitable aqueous solution to the reaction mixture. When an aqueous solution is to be used, an acidic aqueous solution in which hydrochloric acid, sulfuric acid, ammonium chloride or the like is dissolved, an alkaline aqueous solution in which potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate or the like is dissolved, an aqueous solution in which a salt containing a sulfur atom such as sodium thiosulfate, sodium sulfite or the like is dissolved or a saline solution or the like can be optionally used. At the time of the liquid separating operation, if necessary, it is possible to add a solvent which is immiscible with water including benzene based solvents such as toluene, xylene, benzene, chlorobenzene and dichlorobenzene, ester solvents such as ethyl acetate, isopropyl acetate and butyl acetate, ether solvents such as diethyl ether, diisopropyl ether and methyl-t-butyl ether, halogen based solvents such as dichloromethane, dichloroethane and chloroform, hydrocarbon solvents such as hexane, heptane, cyclohexane and methylcyclohexane, and the like. In addition, it is possible to use these solvents singly or to mix two or more kinds with an optional ratio. The number of times of the liquid separation is not particularly limited, and may be carried out in accordance with the purity and yield to be desired.

(714) The reaction mixture obtained above which contains the compound represented by Formula (1-n) may be dehydrated with a drying agent such as sodium sulfate and magnesium sulfate, but this is not essential.

(715) The reaction mixture obtained above which contains the compound represented by Formula (1-n) may be distilled under reduced pressure to remove the solvent as long as the compound is not decomposed.

(716) The reaction mixture obtained after distillation of the solvent which contains the compound represented by Formula (1-n) may be purified by washing, reprecipitation, recrystallization, column chromatography and the like, using a suitable solvent. It may be optionally set in accordance with the desired purity.

(717) [Production Method S]

(718) ##STR03496##

(719) In the formula, Ryg represents a C1-C6 alkoxy group optionally substituted with substituent(s) C, a C1-C6 haloalkoxy group, a C3-C8 cycloalkoxy group optionally substituted with substituent(s) C, a C2-C6 alkenyloxy group optionally substituted with substituent(s) C, a C2-C6 haloalkenyloxy group, a C3-C6 alkynyloxy group optionally substituted with substituent(s) C, a C3-C6 haloalkynyloxy group, a heteroaryl group optionally substituted with substituent(s) D, an aryloxy group optionally substituted with substituent(s) D, a heteroaryloxy group optionally substituted with substituent(s) D, an aralkyloxy group optionally substituted with substituent(s) D, RaRbN— (here, Ra and Rb are the same as defined hereinabove), Rc-L- (wherein Rc and L are the same as defined hereinabove.) or Rx4Rx5C═N—O— (here, Rx4 and Rx5 are the same as defined hereinabove), and R1, R2, Ryc, Het, X, Yc, Q and the broken line are the same as defined hereinabove. The Ryc in the compound represented by Formula (1-i) and the Ryg in the compound represented by Formula (1-o) represent a substituent corresponding to either of R4 or R5, or each other's substituents.

(720) Production Method S is a method of obtaining a compound represented by Formula (1-o), which belongs to the compounds represented by Formula (1) wherein Ryg is a C1-C6 alkoxy group optionally substituted with substituent(s) C, a C1-C6 haloalkoxy group, a C3-C8 cycloalkoxy group optionally substituted with substituent(s) C, a C2-C6 alkenyloxy group optionally substituted with substituent(s) C, a C2-C6 haloalkenyloxy group, a C3-C6 alkynyloxy group optionally substituted with substituent(s) C, a C3-C6 haloalkynyloxy group, a heteroaryl group optionally substituted with substituent(s) D, an aryloxy group optionally substituted with substituent(s) D, a heteroaryloxy group optionally substituted with substituent(s) D, an aralkyloxy group optionally substituted with substituent(s) D, RaRbN— (here, Ra and Rb are the same as defined hereinabove), Rc-L- (wherein Rc and L are the same as defined hereinabove.) or Rx4Rx5C═N—O— (here, Rx4 and Rx5 are the same as defined hereinabove), and is a production method which comprises reacting a compound represented by Formula (1-i) and Ryg-Q in the presence of a base in a solvent.

(721) In the compounds represented by Formula (1-i), preferable Ryc is a fluorine atom, a chlorine atom or a bromine atom.

(722) The Ryg-Q to be used in the present reaction can be obtained as a commercially available product or produced by a conventionally known method. Preferable Q is a hydrogen atom or an alkali metal such as sodium, potassium and the like.

(723) An amount of the Ryg-Q to be used in the present reaction may be 1 equivalent or more relative to the compound represented by Formula (1-i), which is not particularly limited as long as the target reaction proceeds, and is usually 1 equivalent or more and 30 equivalents or less. Also, when Q represents a hydrogen atom, it may be used as a solvent.

(724) The base to be used in the present reaction is preferably inorganic bases such as sodium carbonate, potassium carbonate, cesium carbonate and sodium hydride. In addition, when Q is an alkali metal, use of the base is not essential.

(725) An amount of the base to be used in the present reaction may be 1 equivalent or more relative to the compound represented by Formula (1-i), which is not particularly limited as long as the target reaction proceeds, and is usually 1 equivalent or more and 30 equivalents or less.

(726) The solvent to be used in the present reaction is not particularly limited as long as the target reaction proceeds, and may include alcohol solvents represented by Ryg-H (wherein Ryg is the same as defined hereinabove), ether solvents such as diethyl ether, diisopropyl ether, methyl-t-butyl ether, dimethoxyethane, tetrahydrofuran and dioxane, benzene based solvents such as benzene, toluene, xylene, mesitylene, chlorobenzene and dichlorobenzene, ester solvents such as ethyl acetate, isopropyl acetate and butyl acetate, nitrile solvents, such as acetonitrile, amide solvents such as N-methylpyrrolidone, N,N-dimethylformamide and N,N-dimethylacetamide, urea solvents such as 1,3-dimethyl-2-imidazolidinone, halogen based solvents such as dichloromethane, dichloroethane, chloroform and carbon tetrachloride, sulfur solvents such as dimethylsulfoxide and sulforane, ketone solvents such as acetone, methyl ethyl ketone and methyl isobutyl ketone, and the like. These solvents may be used singly, or two or more kinds may be used in combination in an optional ratio.

(727) An amount of the solvent to be used in the present reaction is not particularly limited as long as the target reaction proceeds, and is usually 3 times by weight or more and 200 times by weight or less relative to the compound represented by Formula (1-i).

(728) A temperature to carry out the present reaction is not particularly limited as long as the target reaction proceeds, and is usually 0° C. or higher and 150° C. or lower or a boiling point of the solvent or lower.

(729) As a post treatment after the reaction, it is possible to carry out a liquid separating operation by adding water or a suitable aqueous solution to the reaction mixture. When an aqueous solution is to be used, an acidic aqueous solution in which hydrochloric acid, sulfuric acid, ammonium chloride or the like is dissolved, an alkaline aqueous solution in which potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate or the like is dissolved, an aqueous solution in which a salt containing a sulfur atom such as sodium thiosulfate, sodium sulfite or the like is dissolved or a saline solution or the like can be optionally used. At the time of the liquid separating operation, if necessary, it is possible to add a solvent which is immiscible with water including benzene based solvents such as toluene, xylene, benzene, chlorobenzene and dichlorobenzene, ester solvents such as ethyl acetate, isopropyl acetate and butyl acetate, ether solvents such as diethyl ether, diisopropyl ether and methyl-t-butyl ether, halogen based solvents such as dichloromethane, dichloroethane, chloroform and carbon tetrachloride, hydrocarbon solvents such as hexane, heptane, cyclohexane and methylcyclohexane, and the like. In addition, it is possible to use these solvents singly or to mix two or more kinds with an optional ratio. The number of times of the liquid separation is not particularly limited, and may be carried out in accordance with the purity and yield to be desired.

(730) The reaction mixture obtained above which contains the compound represented by Formula (1-o) may be dehydrated with a drying agent such as sodium sulfate and magnesium sulfate, but this is not essential.

(731) The reaction mixture obtained above which contains the compound represented by Formula (1-o) may be distilled under reduced pressure to remove the solvent as long as the compound is not decomposed.

(732) The reaction mixture obtained after distillation of the solvent which contains the compound represented by Formula (1-o) may be purified by washing, reprecipitation, recrystallization, column chromatography and the like, using a suitable solvent. It may be optionally set in accordance with the desired purity.

(733) [Production Method T]

(734) ##STR03497##

(735) In the formula, p represents an integer of 1 to 2, and R1, R2, X, Y and the broken line are the same as defined hereinabove.

(736) Production Method T is a synthetic method of a compound represented by Formula (1-p), which belongs to atoms among the compounds represented by Formula (1) wherein Het is a 3 to 6-membered ring group containing 1 to 2 oxygen, and is a production method which comprises reacting a compound represented by Formula (4) and a glycol in the presence of an acid in a solvent.

(737) The compound represented by Formula (4) to be used in the present reaction can be obtained with reference to Reference Examples.

(738) The acid to be used in the present reaction may be exemplified by an inorganic acid such as hydrochloric acid and sulfuric acid, and an organic acid such as p-toluenesulfonic acid and the like, which is not particularly limited as long as the target reaction proceeds.

(739) An amount of the acid to be used in the present reaction may be 0.01 equivalent or more relative to the compound represented by Formula (4), which is not particularly limited as long as the target reaction proceeds, and preferably 0.1 equivalent or more and 1 equivalent or less.

(740) The glycols to be used in the present reaction may be exemplified by ethylene glycol and propylene glycol, and can be obtained as commercially available products or produced by a conventionally known method.

(741) An amount of the glycols to be used in the present reaction may be 1 equivalent or more relative to the compound represented by Formula (4), which is not particularly limited as long as the target reaction proceeds, and preferably 1 equivalent or more and 30 equivalent or less.

(742) The solvent to be used in the present reaction is not particularly limited as long as the target reaction proceeds, and may include benzene based solvents such as benzene, toluene, xylene, mesitylene, chlorobenzene and dichlorobenzene, halogen based solvents such as dichloromethane, dichloroethane, chloroform and carbon tetrachloride, hydrocarbon solvents such as hexane, heptane, cyclohexane and methylcyclohexane, and the like. These solvents may be used singly, or two or more kinds may be used in combination in an optional ratio.

(743) An amount of the solvent to be used in the present reaction is not particularly limited as long as the target reaction proceeds, and is usually 1 time by weight or more and 200 times by weight or less relative to the compound represented by Formula (4).

(744) A temperature to carry out the present reaction is not particularly limited as long as the target reaction proceeds, and is usually −80° C. or higher and 150° C. or lower or a boiling point of the solvent or lower.

(745) As a post treatment after the reaction, it is possible to carry out a liquid separating operation by adding water or a suitable aqueous solution to the reaction mixture. When an aqueous solution is to be used, an acidic aqueous solution in which hydrochloric acid, sulfuric acid, ammonium chloride or the like is dissolved, an alkaline aqueous solution in which potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate or the like is dissolved or a saline solution or the like can be optionally used. At the time of the liquid separating operation, if necessary, it is possible to add a solvent which is immiscible with water including benzene based solvents such as toluene, xylene, benzene, chlorobenzene and dichlorobenzene, ester solvents such as ethyl acetate, isopropyl acetate and butyl acetate, ether solvents such as diethyl ether, diisopropyl ether and methyl-t-butyl ether, halogen based solvents such as dichloromethane, dichloroethane, chloroform and carbon tetrachloride, hydrocarbon solvents such as hexane, heptane, cyclohexane and methylcyclohexane, and the like. In addition, it is possible to use these solvents singly or to mix two or more kinds with an optional ratio. The number of times of the liquid separation is not particularly limited, and may be carried out in accordance with the purity and yield to be desired.

(746) The reaction mixture obtained above which contains the compound represented by Formula (1-p) may be dehydrated with a drying agent such as sodium sulfate and magnesium sulfate, but this is not essential.

(747) The reaction mixture obtained above which contains the compound represented by Formula (1-p) may be distilled off under reduced pressure to remove the solvent as long as the compound is not decomposed.

(748) The reaction mixture obtained after distillation of the solvent which contains the compound represented by Formula (1-p) may be purified by washing, reprecipitation, recrystallization, column chromatography and the like, using a suitable solvent. It may be optionally set in accordance with the desired purity.

(749) [Production Method U]

(750) ##STR03498##

(751) In the formula, Ryh represents a hydrogen atom, a hydroxyl group, a cyano group, a halogen atom, a C1-C6 alkyl group optionally substituted with substituent(s) C, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group optionally substituted with substituent(s) C, a C2-C6 alkenyl group optionally substituted with substituent(s) C, a C2-C6 haloalkenyl group, a C2-C6 alkynyl group optionally substituted with substituent(s) C, a C2-C6 haloalkynyl group, an aryl group optionally substituted with substituent(s) D, a heteroaryl group optionally substituted with substituent(s) D, an aryloxy group optionally substituted with substituent(s) D, a heteroaryloxy group optionally substituted with substituent(s) D, an aralkyloxy group optionally substituted with substituent(s) D, Rx1C(═O)— (wherein Rx1 is the same as defined hereinabove.) or Rx1C(═O)O— (wherein Rx1 is the same as defined hereinabove), Ryi represents a hydrogen atom, a C1-C6 alkyl group optionally substituted with substituent(s) C, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group optionally substituted with substituent(s) C, a C2-C6 alkenyl group optionally substituted with substituent(s) C, a C2-C6 haloalkenyl group, a C2-C6 alkynyl group optionally substituted with substituent(s) C, a C2-C6 haloalkynyl group, an aryl group optionally substituted with substituent(s) D or a heteroaryl group optionally substituted with substituent(s) D, and R1, R2, X, Y and the broken line are the same as defined hereinabove.

(752) The production method U is a synthetic method of a compound represented by Formula (I-q) and a compound represented by Formula (1-r) which belong to the compounds represented by Formula (1), and is a production method which comprises reacting a compound represented by Formula (4-a) and NH2NH-Ryi in a solvent.

(753) A ratio of the compound represented by Formula (1-q) and the compound represented by Formula (1-r) may be either one, thereof alone or a mixture thereof with an optional ratio, which is not particularly limited.

(754) The compound represented by Formula (4-a) to be used in the present reaction can be obtained with reference to Reference Examples.

(755) The NH.sub.2NH-Ryi to be used in the present reaction can be obtained as a commercially available product or produced by a conventionally known method. The NH.sub.2NH-Ryi may form a salt with an acidic compound such as hydrochloric acid and acetic acid, and is not particularly limited as long as the target reaction proceeds.

(756) An amount of the NH.sub.2NH-Ryi to be used in the present reaction may be 1 equivalent or more relative to the compound represented by Formula (4-a), which is not particularly limited as long as the target reaction proceeds, and is usually 1 equivalent or more and 30 equivalents or less.

(757) The solvent to be used in the present reaction is not particularly limited as long as the target reaction proceeds, and may include alcohol solvents such as methanol, ethanol, propanol and butanol, ether solvents such as diethyl ether, diisopropyl ether, methyl-t-butyl ether, dimethoxyethane, tetrahydrofuran and dioxane, benzene based solvents such as benzene, toluene, xylene, mesitylene, chlorobenzene and dichlorobenzene, ester solvents such as ethyl acetate, isopropyl acetate and butyl acetate, amide solvents such as N-methylpyrrolidone, N,N-dimethylformamide and N,N-dimethylacetamide, urea solvents such as 1,3-dimethyl-2-imidazolidinone, halogen based solvents such as dichloromethane, dichloroethane, chloroform and carbon tetrachloride, sulfur solvents such as dimethylsulfoxide and sulforane, ketone solvents such as acetone, methyl ethyl ketone and methyl isobutyl ketone, and the like. These solvents may be used singly, or two or more kinds may be used in combination in an optional ratio.

(758) An amount of the solvent to be used in the present reaction is not particularly limited as long as the target reaction proceeds, and is usually 3 times by weight or more and 200 times by weight or less relative to the compound represented by Formula (4-a).

(759) A temperature to carry out the present reaction is not particularly limited as long as the target reaction proceeds, and is usually 0° C. or higher and 150° C. or lower or a boiling point of the solvent or lower.

(760) As a post treatment after the reaction, it is possible to carry out a liquid separating operation by adding water or a suitable aqueous solution to the reaction mixture. When an aqueous solution is to be used, an acidic aqueous solution in which hydrochloric acid, sulfuric acid, ammonium chloride or the like is dissolved, an alkaline aqueous solution in which potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate or the like is dissolved, an aqueous solution in which a salt containing a sulfur atom such as sodium thiosulfate, sodium sulfite or the like is dissolved or a saline solution or the like can be optionally used. At the time of the liquid separating operation, if necessary, it is possible to add a solvent which is immiscible with water including benzene based solvents such as toluene, xylene, benzene, chlorobenzene and dichlorobenzene, ester solvents such as ethyl acetate, isopropyl acetate and butyl acetate, ether solvents such as diethyl ether, diisopropyl ether and methyl-t-butyl ether, halogen based solvents such as dichloromethane, dichloroethane, chloroform and carbon tetrachloride, hydrocarbon solvents such as hexane, heptane, cyclohexane and methylcyclohexane, and the like. In addition, it is possible to use these solvents singly or to mix two or more kinds with an optional ratio. The number of times of the liquid separation is not particularly limited, and may be carried out in accordance with the purity and yield to be desired.

(761) The reaction mixture obtained above which contains the compound represented by Formula (1-q) and the compound represented by Formula (1-r) may be dehydrated with a drying agent such as sodium sulfate and magnesium sulfate, but this is not essential.

(762) The reaction mixture obtained above which contains the compound represented by Formula (1-q) and the compound represented by Formula (1-r) may be distilled under reduced pressure to remove the solvent as long as the compound is not decomposed.

(763) The reaction mixture obtained after distillation of the solvent which contains the compound represented by Formula (1-q) and the compound represented by Formula (1-r) may be purified by washing, reprecipitation, recrystallization, column chromatography and the like, using a suitable solvent. It may be optionally set in accordance with the desired purity.

(764) [Production Method V]

(765) ##STR03499##

(766) In the formula, La represents S, Lb represents SO or SO.sub.2, and Ox′ represents an oxidizing agent.

(767) The production method V is a production method of a compounds represented by Formula (Lb), which belongs to in the compounds represented by Formula (1) represented by the formula (1) wherein Lb contained in R2, R3, R4, R5, substituent(s) A and substituent(s) C is SO or SO.sub.2, and is a production method which comprises reacting a compound represented by Formula (La), which belongs to the compounds represented by Formula (1) wherein La contained in R2, R3, R4, R5, substituent(s) A and substituent(s) C is S and an oxidizing agent (Ox′) in a solvent.

(768) The oxidizing agent to be used in the present reaction may include a peroxide such as aqueous hydrogen peroxide, meta-chloroperbenzoic acid and the like. In addition, a transition metal such as sodium tungstate may be added.

(769) An amount of the oxidizing agent to be used in the present reaction may be usually 1.0 equivalent or more and 1.2 equivalents or less relative to the compound represented by Formula (La) when SO is produced, and is usually 2 equivalents or more and 10 equivalents or less when SO.sub.2 is produced. In addition, when the transition metal is to be added, it is usually used in 0.001 equivalent or more and 1 equivalent or less.

(770) The solvent to be used in the present reaction is not particularly limited as long as the target reaction proceeds, and may include water solvent, an acidic solvent such as acetic acid, benzene based solvents such as benzene, toluene, xylene, mesitylene, chlorobenzene and dichlorobenzene, nitrile solvents such as acetonitrile, halogen based solvents such as dichloromethane, dichloroethane, chloroform and carbon tetrachloride, and the like. These solvents may be used singly, or two or more kinds may be used in combination in an optional ratio.

(771) An amount of the solvent to be used in the present reaction is not particularly limited as long as the target reaction proceeds, and is usually 3 times by weight or more and 200 times by weight or less relative to the compound represented by Formula (La).

(772) A temperature to carry out the present reaction is not particularly limited as long as the target reaction proceeds, and is usually −10° C. or higher and 120° C. or lower or a boiling point of the solvent or lower.

(773) As a post treatment after the reaction, it is possible to carry out a liquid separating operation by adding water or a suitable aqueous solution to the reaction mixture. When an aqueous solution is to be used, an acidic aqueous solution in which hydrochloric acid, sulfuric acid, ammonium chloride or the like is dissolved, an alkaline aqueous solution in which potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate or the like is dissolved, an aqueous solution in which a salt containing a sulfur atom such as sodium thiosulfate, sodium sulfite or the like is dissolved or a saline solution or the like can be optionally used. At the time of the liquid separating operation, if necessary, it is possible to add a solvent which is immiscible with water including benzene based solvents such as toluene, xylene, benzene, chlorobenzene and dichlorobenzene, ester solvents such as ethyl acetate, isopropyl acetate and butyl acetate, ether solvents such as diethyl ether, diisopropyl ether and methyl-t-butyl ether, halogen based solvents such as dichloromethane, dichloroethane, chloroform and carbon tetrachloride, hydrocarbon solvents such as hexane, heptane, cyclohexane and methylcyclohexane, and the like.

(774) In addition, it is possible to use these solvents singly or to mix two or more kinds with an optional ratio. The number of times of the liquid separation is not particularly limited, and may be carried out in accordance with the purity and yield to be desired.

(775) The reaction mixture obtained above which contains the compound represented by Formula (Lb) may be dehydrated with a drying agent such as sodium sulfate and magnesium sulfate, but this is not essential.

(776) The reaction mixture obtained above which contains the compound represented by Formula (Lb) may be distilled under reduced pressure to remove the solvent as long as the compound is not decomposed.

(777) The reaction mixture obtained after distillation of the solvent which contains the compound represented by Formula (Lb) may be purified by washing, reprecipitation, recrystallization, column chromatography and the like, using a suitable solvent. It may be optionally set in accordance with the desired purity.

(778) Next, a synthetic method of the compound represented by Formula (3) described in Production Method A will be described.

(779) [Production Method W]

(780) ##STR03500##

(781) In the formula, R2, R6, Het, X and Y are the same as defined hereinabove.

(782) The production method W is a production method of a production intermediate represented by the compound of Formula (3), and is a production method which comprises reacting a compound represented by Formula (5) and a compound represented by Formula (6) in the presence of a base in a solvent.

(783) The compound represented by Formula (5) to be used in the present reaction can be synthesized in accordance with Reference Examples. In addition, it can be synthesized with reference to Green Chemistry, vol. 41, pp. 580-585, The Journal of Organic Chemistry, vol. 65, No. 20, pp. 6458-6461 (2000) or U.S. Pat. No. 5,922,718.

(784) The compound represented by Formula (6) to be used in the present reaction can be obtained as a commercially available product or produced by a conventionally known method.

(785) An amount of the compound represented by Formula (6) to be used in the present reaction may be 1 equivalent or more relative to the compound represented by Formula (5), which is not particularly limited as long as the target reaction proceeds, and preferably 1 equivalent or more and 3 equivalents or less.

(786) The base to be used in the present reaction may include inorganic bases such as sodium carbonate, potassium carbonate, cesium carbonate and tripotassium phosphate, or metal alkoxides such as sodium methoxide, sodium ethoxide and potassium t-butoxide.

(787) The base to be used in the present reaction can be carried out with a catalytic amount, which is not particularly limited as long as the target reaction proceeds, and preferably 0.01 equivalent or more and 3 equivalents or less relative to the compound represented by Formula (5).

(788) The solvents to be used in the present reaction may include ether solvents such as diethyl ether, diisopropyl ether, methyl-t-butyl ether, dimethoxyethane, tetrahydrofuran and dioxane, benzene based solvents such as benzene, toluene, xylene, mesitylene, chlorobenzene and dichlorobenzene, ester solvents such as ethyl acetate, isopropyl acetate and butyl acetate, nitrile solvents such as acetonitrile, amide solvents such as N-methylpyrrolidone, N,N-dimethylformamide and N,N-dimethylacetamide, urea solvents such as 1,3-dimethyl-2-imidazolidinone, halogen based solvents such as dichloromethane, dichloroethane, chloroform and carbon tetrachloride, sulfur solvents such as dimethylsulfoxide and sulforane, ketone solvents such as acetone, methyl ethyl ketone and methyl isobutyl ketone, and the like. These solvents may be used singly, or two or more kinds may be used in combination in an optional ratio.

(789) An amount of the solvent to be used in the present reaction is not particularly limited as long as the target reaction proceeds, and is usually 3 times by weight or more and 200 times by weight or less relative to the compound represented by Formula (5).

(790) A temperature to carry out the present reaction is not particularly limited as long as the target reaction proceeds, and is usually −50° C. or higher and 150° C. or lower or a boiling point of the solvent or lower.

(791) As a post treatment after the reaction, it is possible to carry out a liquid separating operation by adding water or a suitable aqueous solution to the reaction mixture. When an aqueous solution is to be used, an acidic aqueous solution in which hydrochloric acid, sulfuric acid or the like is dissolved, an alkaline aqueous solution in which potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate or the like is dissolved or a saline solution or the like can be optionally used. At the time of the liquid separating operation, if necessary, it is possible to add a solvent which is immiscible with water including benzene based solvents such as toluene, xylene, benzene, chlorobenzene and dichlorobenzene, ester solvents such as ethyl acetate, isopropyl acetate and butyl acetate, ether solvents such as diethyl ether, diisopropyl ether and methyl-t-butyl ether, halogen based solvents such as dichloromethane, dichloroethane, chloroform and carbon tetrachloride, hydrocarbon solvents such as hexane, heptane, cyclohexane and methylcyclohexane, and the like. In addition, it is possible to use these solvents singly or to mix two or more kinds with an optional ratio. The number of times of the liquid separation is not particularly limited, and may be carried out in accordance with the purity and yield to be desired.

(792) The reaction mixture obtained above which contains the compound represented by Formula (3) may be dehydrated with a drying agent such as sodium sulfate and magnesium sulfate, but this is not essential.

(793) The reaction mixture obtained above which contains the compound represented by Formula (3) may be distilled under reduced pressure to remove the solvent as long as the compound is not decomposed.

(794) The reaction mixture obtained after distillation of the solvent which contains the compound represented by Formula (3) may be purified by washing, reprecipitation, recrystallization, column chromatography and the like, using a suitable solvent. It may be optionally set in accordance with the desired purity.

(795) [Production Method X]

(796) ##STR03501##

(797) In the formula, R6a represents a C1-C6 alkyl group, and R2, Het, X and Y are the same as defined hereinabove.

(798) Production Method X is a production method of a production intermediate represented by Formula (3b) which belongs to the compounds represented by Formula (3), and is a production method which comprises reacting a compound represented by Formula (3a) under acidic conditions or basic conditions in a solvent.

(799) First, the reaction under acidic conditions will be described.

(800) The acid to be used in the present reaction may be exemplified by inorganic acids such as hydrochloric acid, hydrobromic acid and phosphoric acid, and organic acids such as acetic acid, methanesulfonic acid, p-toluenesulfonic acid and trifluoroacetic acid. It is not particularly limited as long as the target reaction proceeds.

(801) An amount of the acid to be used in the present reaction may be a catalytic amount, which is not particularly limited as long as the target reaction proceeds, and preferably 0.01 equivalent or more relative to the compound represented by Formula (3a). In addition, with regard to a liquid state acid, it is also possible to use it as a solvent.

(802) The solvent to be used in the present reaction is not particularly limited as long as the target reaction proceeds, and may include water solvent, acidic solvents such as acetic acid and methanesulfonic acid, ether solvents such as diethyl ether, diisopropyl ether, methyl-t-butyl ether, dimethoxyethane, tetrahydrofuran and dioxane, alcohol solvents such as methanol, ethanol and isopropanol, benzene based solvents such as benzene, toluene, xylene, mesitylene, chlorobenzene and dichlorobenzene, ester solvents such as ethyl acetate, isopropyl acetate and butyl acetate, nitrile solvents such as acetonitrile, amide solvents such as N-methylpyrrolidone, N,N-dimethylformamide and N,N-dimethylacetamide, urea solvents such as 1,3-dimethyl-2-imidazolidinone, halogen based solvents such as dichloromethane, dichloroethane, chloroform and carbon tetrachloride, and the like. These solvents may be used singly, or two or more kinds may be used in combination in an optional ratio.

(803) An amount of the solvent to be used in the present reaction is not particularly limited as long as the target reaction proceeds, and is usually 3 times by weight or more and 200 times by weight or less relative to the compound represented by Formula (3a).

(804) A temperature to carry out the present reaction is not particularly limited as long as the target reaction proceeds, and is usually 0° C. or higher and 180° C. or lower or a boiling point of the solvent or lower.

(805) Next, the reaction under basic conditions will be described.

(806) The base to be used in the present reaction may be exemplified by inorganic bases such as lithium hydroxide, sodium hydroxide and potassium hydroxide, and is not particularly limited as long as the target reaction proceeds.

(807) The base to be used in the present reaction may be 1 equivalent or more relative to the compound represented by Formula (3a), which is not particularly limited as long as the target reaction proceeds, and preferably 1 equivalent or more and 30 equivalents or less.

(808) The solvent to be used in the present reaction is not particularly limited as long as the target reaction proceeds, and may include water solvent, ether solvents such as diethyl ether, diisopropyl ether, methyl-t-butyl ether, dimethoxyethane, tetrahydrofuran and dioxane, alcohol solvents such as methanol, ethanol and isopropanol, benzene based solvents such as benzene, toluene, xylene, mesitylene, chlorobenzene and dichlorobenzene, ester solvents such as ethyl acetate, isopropyl acetate and butyl acetate, nitrile solvents such as acetonitrile, amide solvents such as N-methylpyrrolidone, N,N-dimethylformamide and N,N-dimethylacetamide, urea solvents such as 1,3-dimethyl-2-imidazolidinone, halogen based solvents such as dichloromethane, dichloroethane, chloroform and carbon tetrachloride, and the like. These solvents may be used singly, or two or more kinds may be used in combination in an optional ratio.

(809) An amount of the solvent to be used in the present reaction is not particularly limited as long as the target reaction proceeds, and is usually 3 times by weight or more and 200 times by weight or less relative to the compound represented by Formula (3a).

(810) A temperature to carry out the present reaction is not particularly limited as long as the target reaction proceeds, and is usually −20° C. or higher and 180° C. or lower or a boiling point of the solvent or lower.

(811) A post treatment after the reaction can be carried out in the same way as the reaction under acidic conditions and the reaction under basic conditions. It is possible to carry out a liquid separating operation by adding water or a suitable aqueous solution to the reaction mixture. When an aqueous solution is to be used, an acidic aqueous solution in which hydrochloric acid, sulfuric acid or the like is dissolved, an alkaline aqueous solution in which potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate or the like is dissolved, and a saline solution can be optionally used. At the time of the liquid separating operation, if necessary, it is possible to add a solvent which is immiscible with water including benzene based solvents such as toluene, xylene, benzene, chlorobenzene and dichlorobenzene, ester solvents such as ethyl acetate, isopropyl acetate and butyl acetate, ether solvents such as diethyl ether, diisopropyl ether and methyl-t-butyl ether, halogen based solvents such as dichloromethane, dichloroethane, chloroform and carbon tetrachloride, hydrocarbon solvents such as hexane, heptane, cyclohexane and methylcyclohexane, and the like. In addition, it is possible to use these solvents singly or to mix two or more kinds with an optional ratio. The number of times of the liquid separation is not particularly limited, and may be carried out in accordance with the purity and yield to be desired.

(812) The reaction mixture obtained above which contains the compound represented by Formula (3b) may be dehydrated with a drying agent such as sodium sulfate and magnesium sulfate, but this is not essential.

(813) The reaction mixture obtained above which contains the compound represented by Formula (3b) may be distilled under reduced pressure to remove the solvent as long as the compound is not decomposed.

(814) The reaction mixture obtained after distillation of the solvent which contains the compound represented by Formula (3b) may be purified by washing, reprecipitation, recrystallization, column chromatography and the like, using a suitable solvent. It may be optionally set in accordance with the desired purity.

(815) The compound represented by Formula (3b) contains an isomer represented by Formula (3b′)

(816) ##STR03502##
(wherein R2, Het, X and Y are the same as defined hereinabove).

(817) The compound represented by Formula (3b′) can be handled similar to the compound represented by Formula (3b), and Production Method A can be applied.

(818) Also, the compound represented by Formula (3b′) contains an asymmetric carbon, and a mixed ratio of the isomers may be a single isomer alone or a mixture with an optional ratio. Further, it may be a mixture of the compound represented by Formula (3b) and the compound represented by Formula (3b′), and a mixed ratio of the isomers may be a single isomer alone or a mixture with an optional ratio.

(819) [Production Method Y]

(820) ##STR03503##

(821) In the formula, Ryj represents a hydrogen atom, a C1-C6 alkyl group optionally substituted with substituent(s) C, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group optionally substituted with substituent(s) C, a C2-C6 alkenyl group optionally substituted with substituent(s) C, a C2-C6 haloalkenyl group, a C2-C6 alkynyl group optionally substituted with substituent(s) C, a C2-C6 haloalkynyl group, an aryl group optionally substituted with substituent(s) D or a heteroaryl group optionally substituted with substituent(s) D, and R1, R2, X, Y and the broken line are the same as defined hereinabove.

(822) Production Method Y is a synthetic method of a compound represented by Formula (1-s) which belongs to the compounds represented by Formula (1), and is a production method which comprises reacting a compound represented by Formula (4) and a compound represented by Formula (7) in the presence of a base in a solvent.

(823) The compound represented by Formula (4) to be used in the present reaction can be obtained with reference to Reference Examples.

(824) The compound represented by Formula (7) to be used in the present reaction can be obtained as a commercially available product or produced by a conventionally known method.

(825) An amount of the compound represented by Formula (7) to be used in the present reaction may be 1 equivalent or more relative to the compound represented by Formula (4), which is not particularly limited as long as the target reaction proceeds, and is usually 1 equivalent or more and 10 equivalents or less.

(826) The base to be used in the present reaction may be exemplified by inorganic bases such as sodium hydride, lithium hydroxide, sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, cesium carbonate and tripotassium phosphate, and metal alkoxides such as sodium methoxide, sodium ethoxide and potassium t-butoxide, and is not particularly limited as long as the target reaction proceeds.

(827) An amount of the base to be used in the present reaction may be 1 equivalent or more relative to the compound represented by Formula (4), which is not particularly limited as long as the target reaction proceeds, and is usually 1 equivalent or more and 10 equivalents or less.

(828) The solvent to be used in the present reaction is not particularly limited as long as the target reaction proceeds, and may include alcohol solvents such as methanol, ethanol, propanol and butanol, ether solvents such as diethyl ether, diisopropyl ether, methyl-t-butyl ether, dimethoxyethane, tetrahydrofuran and dioxane, benzene based solvents such as benzene, toluene, xylene, mesitylene, chlorobenzene and dichlorobenzene, ester solvents such as ethyl acetate, isopropyl acetate and butyl acetate, amide solvents such as N-methylpyrrolidone, N,N-dimethylformamide and N,N-dimethylacetamide, urea solvents such as 1,3-dimethyl-2-imidazolidinone, halogen based solvents such as dichloromethane, dichloroethane, chloroform and carbon tetrachloride, sulfur solvents such as dimethylsulfoxide and sulforane, ketone solvents such as acetone, methyl ethyl ketone and methyl isobutyl ketone, and the like. These solvents may be used singly, or two or more kinds may be used in combination in an optional ratio.

(829) An amount of the solvent to be used in the present reaction is not particularly limited as long as the target reaction proceeds, and is usually 3 times by weight or more and 200 times by weight or less relative to the compound represented by Formula (4).

(830) A temperature to carry out the present reaction is not particularly limited as long as the target reaction proceeds, and is usually 0° C. or higher and 150° C. or lower or a boiling point of the solvent or lower.

(831) As a post treatment after the reaction, it is possible to carry out a liquid separating operation by adding water or a suitable aqueous solution to the reaction mixture. When an aqueous solution is to be used, an acidic aqueous solution in which hydrochloric acid, sulfuric acid, ammonium chloride or the like is dissolved, an alkaline aqueous solution in which potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate or the like is dissolved, an aqueous solution in which a salt containing a sulfur atom such as sodium thiosulfate, sodium sulfite or the like is dissolved or a saline solution or the like can be optionally used. At the time of the liquid separating operation, if necessary, it is possible to add a solvent which is immiscible with water including benzene based solvents such as toluene, xylene, benzene, chlorobenzene and dichlorobenzene, ester solvents such as ethyl acetate, isopropyl acetate and butyl acetate, ether solvents such as diethyl ether, diisopropyl ether and methyl-t-butyl ether, halogen based solvents such as dichloromethane, dichloroethane, chloroform and carbon tetrachloride, hydrocarbon solvents such as hexane, heptane, cyclohexane and methylcyclohexane, and the like. In addition, it is possible to use these solvents singly or to mix two or more kinds with an optional ratio. The number of times of the liquid separation is not particularly limited, and may be carried out in accordance with the purity and yield to be desired.

(832) The reaction mixture obtained above which contains the compound represented by Formula (1-s) may be dehydrated with a drying agent such as sodium sulfate and magnesium sulfate, but this is not essential.

(833) The reaction mixture obtained above which contains the compound represented by Formula (1-s) may be distilled under reduced pressure to remove the solvent as long as the compound is not decomposed.

(834) The reaction mixture, obtained after distillation of the solvent which contains the compound represented by Formula (1-s) may be purified by washing, reprecipitation, recrystallization, column chromatography and the like, using a suitable solvent. It may be optionally set in accordance with the desired purity.

(835) [Production Method Z]

(836) ##STR03504##

(837) In the formula, Ryk represents a hydrogen atom, a cyano group, a nitro group, a C1-C6 alkyl group optionally substituted with substituent(s) C, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group optionally substituted with substituent(s) C, a C2-C6 alkenyl group optionally substituted with substituent(s) C, a C2-C6 haloalkenyl group, a C2-C6 alkynyl group optionally substituted with substituent(s) C, a C2-C6 haloalkynyl group, a C1-C6 alkoxy group optionally substituted with substituent(s) C, a C1-C6 haloalkoxy group or Rx1C(═O)— (wherein Rx1 is the same as defined hereinabove), and R1, R2, Ryj, X, Y and the broken line are the same as defined hereinabove.

(838) The production method Z is a synthetic method of a compound represented by Formula (1-t) which belongs to the compounds represented by Formula (1), and is a production method which comprises reacting a compound represented by Formula (8) and a compound represented by Formula (7) in the presence of a base in a solvent.

(839) The compound represented by Formula (8) to be used in the present reaction can be obtained with reference to Reference Examples. The compound represented by Formula (8) contains geometric isomers, a mixed ratio of the isomers may be a single isomer alone or a mixture with an optional ratio, and is not particularly limited as long as the target reaction proceeds.

(840) The compound represented by Formula (7) to be used in the present reaction can be obtained as a commercially available product or produced by a conventionally known method.

(841) An amount of the compound represented by Formula (7) to be used in the present reaction may be 1 equivalent or more relative to the compound represented by Formula (8), which is not particularly limited as long as the target reaction proceeds, and is usually 1 equivalent or more and 10 equivalents or less.

(842) The base to be used in the present reaction may be exemplified by inorganic bases such as sodium hydride, lithium hydroxide, sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, cesium carbonate and tripotassium phosphate, and metal alkoxides such as sodium methoxide, sodium ethoxide and potassium t-butoxide, and is not particularly limited as long as the target reaction proceeds.

(843) An amount of the base to be used in the present reaction may be 1 equivalent or more relative to the compound represented by Formula (8), which is not particularly limited as long as the target reaction proceeds, and is usually 1 equivalent or more and 10 equivalents or less.

(844) The solvent to be used in the present reaction is not particularly limited as long as the target reaction proceeds, and may include alcohol solvents such as methanol, ethanol, propanol and butanol, ether solvents such as diethyl ether, diisopropyl ether, methyl-t-butyl ether, dimethoxyethane, tetrahydrofuran and dioxane, benzene based solvents such as benzene, toluene, xylene, mesitylene, chlorobenzene and dichlorobenzene, ester solvents such as ethyl acetate, isopropyl acetate and butyl acetate, amide solvents such as N-methylpyrrolidone, N,N-dimethylformamide and N,N-dimethylacetamide, urea solvents such as 1,3-dimethyl-2-imidazolidinone, halogen based solvents such as dichloromethane, dichloroethane, chloroform and carbon tetrachloride, sulfur solvents such as dimethylsulfoxide and sulforane, ketone solvents such as acetone, methyl ethyl ketone and methyl isobutyl ketone, and the like. These solvents may be used singly, or two or more kinds may be used in combination in an optional ratio.

(845) An amount of the solvent to be used in the present reaction is not particularly limited as long as the target reaction proceeds, and is usually 3 times by weight or more and 200 times by weight or less relative to the compound represented by Formula (8).

(846) A temperature to carry out the present reaction is not particularly limited as long as the target reaction proceeds, and is usually 0° C. or higher and 150° C. or lower or a boiling point of the solvent or lower.

(847) As a post treatment after the reaction, it is possible to carry out a liquid separating operation by adding water or a suitable aqueous solution to the reaction mixture. When an aqueous solution is to be used, an acidic aqueous solution in which hydrochloric acid, sulfuric acid, ammonium chloride or the like is dissolved, an alkaline aqueous solution in which potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate or the like is dissolved, an aqueous solution in which a salt containing a sulfur atom such as sodium thiosulfate, sodium sulfite or the like is dissolved or a saline solution or the like can be optionally used. At the time of the liquid separating operation, if necessary, it is possible to add a solvent which is immiscible with water including benzene based solvents such as toluene, xylene, benzene, chlorobenzene and dichlorobenzene, ester solvents such as ethyl acetate, isopropyl acetate and butyl acetate, ether solvents such as diethyl ether, diisopropyl ether and methyl-t-butyl ether, halogen based solvents such as dichloromethane, dichloroethane, chloroform and carbon tetrachloride, hydrocarbon solvents such as hexane, heptane, cyclohexane and methylcyclohexane, and the like. In addition, it is possible to use these solvents singly or to mix two or more kinds with an optional ratio. The number of times of the liquid separation is not particularly limited, and may be carried out in accordance with the purity and yield to be desired.

(848) The reaction mixture obtained above which contains the compound represented by Formula (1-t) may be dehydrated with a drying agent such as sodium sulfate and magnesium sulfate, but this is not essential.

(849) The reaction mixture obtained above which contains the compound represented by Formula (1-t) may be distilled under reduced pressure to remove the solvent as long as the compound is not decomposed.

(850) The reaction mixture obtained after distillation of the solvent which contains the compound represented by Formula (1-t) may be purified by washing, reprecipitation, recrystallization, column chromatography and the like, using a suitable solvent. It may be optionally set in accordance with the desired purity.

(851) [Production Method AA]

(852) ##STR03505##

(853) In the formula, R1, Het, R2b, X and Y are the same as defined hereinabove.

(854) Production Method AA is a synthetic method of a compound represented by Formula (1a-f) having a trifluoromethyl group which belongs to the compounds represented by Formula (1a), and is a production method which comprises reacting a compound represented by Formula (1a-b) and methyl difluoro(fluorosulfonyl)acetate in the presence of a transition metal.

(855) In the compound represented by Formula (1a-b), preferable R2b is a chlorine atom, a bromine atom or an iodine atom.

(856) Methyl difluoro(fluorosulfonyl)acetate to be used in the present reaction can be obtained as a commercially available product or produced by a conventionally known method.

(857) An amount of methyl difluoro(fluorosulfonyl)acetate to be used in the present reaction may be 1 equivalent or more relative to the compound represented by Formula (1a-b), which is not particularly limited as long as the target reaction proceeds, and preferably 1 equivalent or more and 50 equivalents or less.

(858) The transition metal to be used in the present reaction is copper and the like. It is preferably copper bromide, copper iodide and the like.

(859) An amount of the transition metal to be used in the present reaction may be 1 equivalent or more relative to the compound represented by Formula (1a-b), which is not particularly limited as long as the target reaction proceeds, and preferably 1 equivalent or more and 50 equivalents or less.

(860) In order to proceed the reaction efficiently, an additive such as ethyldiisopropylamine and hexamethylphosphoric triamide, but it is not essential.

(861) An amount of the additive to be used in the present reaction may be 50 equivalents or less relative to the compound represented by Formula (1a-b), and is not particularly limited as long as the target reaction proceeds.

(862) The solvent to be used in the present reaction is not particularly limited as long as the target reaction proceeds, and may include amide solvents such as N-methylpyrrolidone, N,N-dimethylformamide and N,N-dimethylacetamide, sulfur solvents such as dimethylsulfoxide and sulforane, and the like. These solvents may be used singly, or two or more kinds may be used in combination in an optional ratio.

(863) An amount of the solvent to be used in the present reaction is not particularly limited as long as the target reaction proceeds, and is usually 3 times by weight or more and 200 times by weight or less relative to the compound represented by Formula (1a-b).

(864) A temperature to carry out the present reaction is not particularly limited as long as the target reaction proceeds, and is usually 0° C. or higher and 150° C. or lower or a boiling point of the solvent or lower.

(865) As a post treatment after the reaction, it is possible to carry out a liquid separating operation by adding water or a suitable aqueous solution to the reaction mixture. When an aqueous solution is to be used, an acidic aqueous solution in which hydrochloric acid, sulfuric acid, ammonium chloride or the like is dissolved, an alkaline aqueous solution in which ammonia, potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate or the like is dissolved, an aqueous solution in which a salt containing a sulfur atom such as sodium thiosulfate, sodium sulfite or the like is dissolved or a saline solution or the like can be optionally used. At the time of the liquid separating operation, if necessary, it is possible to add a solvent which is immiscible with water including benzene based solvents such as toluene, xylene, benzene, chlorobenzene and dichlorobenzene, ester solvents such as ethyl acetate, isopropyl acetate and butyl acetate, ether solvents such as diethyl ether, diisopropyl ether and methyl-t-butyl ether, halogen based solvents such as dichloromethane, dichloroethane, chloroform and carbon tetrachloride, hydrocarbon solvents such as hexane, heptane, cyclohexane and methylcyclohexane, and the like. In addition, it is possible to use these solvents singly or to mix two or more kinds with an optional ratio. The number of times of the liquid separation is not particularly limited, and may be carried out in accordance with the purity and yield to be desired.

(866) The reaction mixture obtained above which contains the compound represented by Formula (1a-f) may be dehydrated with a drying agent such as sodium sulfate and magnesium sulfate, but this is not essential.

(867) The reaction mixture obtained above which contains the compound represented by Formula (1a-f) may be distilled under reduced pressure to remove the solvent as long as the compound is not decomposed.

(868) The reaction mixture obtained after distillation of the solvent which contains the compound represented by Formula (1a-f) may be purified by washing, reprecipitation, recrystallization, column chromatography and the like, using a suitable solvent. It may be optionally set in accordance with the desired purity.

(869) [Production Method AB]

(870) ##STR03506##

(871) In the formula, R1, R2, Ryc, Ryg, Het2, X, Y, Q and the broken line are the same as defined hereinabove.

(872) Production Method AB is a method of obtaining a compound represented by Formula (1-u), which belongs to the compounds represented by Formula (1), wherein Ryg is a C1-C6 alkoxy group optionally substituted with substituent(s) C, a C1-C6 haloalkoxy group, a C3-C8 cycloalkoxy group optionally substituted with substituent(s) C, a C2-C6 alkenyloxy group optionally substituted with substituent(s) C, a C2-C6 haloalkenyloxy group, a C3-C6 alkynyloxy group optionally substituted with substituent(s) C, a C3-C6 haloalkynyloxy group, a heteroaryl group optionally substituted with substituent(s) D, an aryloxy group optionally substituted with substituent(s) D, a heteroaryloxy group optionally substituted with substituent(s) D, an aralkyloxy group optionally substituted with substituent(s) D, RaRbN— (here, Ra and Rb are the same as defined hereinabove), Rc-L- (wherein Rc and L are the same as defined hereinabove.) or Rx4Rx5C═N—O— (here, Rx4 and Rx5 are the same as defined hereinabove), and is a production method which comprises reacting a compound represented by Formula (1-g) and Ryg-Q in the presence of a base in a solvent.

(873) In the compound represented by Formula (1-g), preferable Ryc is a fluorine atom, a chlorine atom or a bromine atom.

(874) The Ryg-Q to be used in the present reaction can be obtained as a commercially available product or produced by a conventionally known method. Preferable Q is a hydrogen atom or an alkali metal such as sodium, potassium and the like.

(875) An amount of the Ryg-Q to be used in the present reaction may be 1 equivalent or more relative to the compound represented by Formula (1-g), which is not particularly limited as long as the target reaction proceeds, and is usually 1 equivalent or more and 30 equivalents or less. Also, when Q represents a hydrogen atom, it may be used as a solvent.

(876) The base to be used in the present reaction is preferably inorganic bases such as sodium carbonate, potassium carbonate, cesium carbonate and sodium hydride. Also, when the Q is an alkali metal, then use of the base is not essential.

(877) An amount of the base to be used in the present reaction may be 1 equivalent or more relative to the compound represented by Formula (1-g), which is not particularly limited as long as the target reaction proceeds, and is usually 1 equivalent or more and 30 equivalents or less.

(878) The solvent to be used in the present reaction is not particularly limited as long as the target reaction proceeds, and may include alcohol solvents represented by Ryg-H (wherein Ryg is the same as defined hereinabove), ether solvents such as diethyl ether, diisopropyl ether, methyl-t-butyl ether, dimethoxyethane, tetrahydrofuran and dioxane, benzene based solvents such as benzene, toluene, xylene, mesitylene, chlorobenzene and dichlorobenzene, ester solvents such as ethyl acetate, isopropyl acetate and butyl acetate, nitrile solvents such as acetonitrile, amide solvents such as N-methylpyrrolidone, N,N-dimethylformamide and N,N-dimethylacetamide, urea solvents such as 1,3-dimethyl-2-imidazolidinone, halogen based solvents such as dichloromethane, dichloroethane, chloroform and carbon tetrachloride, sulfur solvents such as dimethylsulfoxide and sulforane, ketone solvents such as acetone, methyl ethyl ketone and methyl isobutyl ketone, and the like. These solvents may be used singly, or two or more kinds may be used in combination in an optional ratio.

(879) An amount of the solvent to be used in the present reaction is not particularly limited as long as the target reaction proceeds, and is usually 3 times by weight or more and 200 times by weight or less relative to the compound represented by Formula (1-g).

(880) A temperature to carry out the present reaction is not particularly limited as long as the target reaction proceeds, and is usually 0° C. or higher and 150° C. or lower or a boiling point of the solvent or lower.

(881) As a post treatment after the reaction, it is possible to carry out a liquid separating operation by adding water or a suitable aqueous solution to the reaction mixture. When an aqueous solution is to be used, an acidic aqueous solution in which hydrochloric acid, sulfuric acid, ammonium chloride or the like is dissolved, an alkaline aqueous solution in which potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate or the like is dissolved, an aqueous solution in which a salt containing a sulfur atom such as sodium thiosulfate, sodium sulfite or the like is dissolved or a saline solution or the like can be optionally used. At the time of the liquid separating operation, if necessary, it is possible to add a solvent which is immiscible with water including benzene based solvents such as toluene, xylene, benzene, chlorobenzene and dichlorobenzene, ester solvents such as ethyl acetate, isopropyl acetate and butyl acetate, ether solvents such as diethyl ether, diisopropyl ether and methyl-t-butyl ether, halogen based solvents such as dichloromethane, dichloroethane, chloroform and carbon tetrachloride; hydrocarbon solvents such as hexane, heptane, cyclohexane and methylcyclohexane, and the like. In addition, it is possible to use these solvents singly or to mix two or more kinds with an optional ratio. The number of times of the liquid separation is not particularly limited, and may be carried out in accordance with the purity and yield to be desired.

(882) The reaction mixture obtained above which contains the compound represented by Formula (1-u) may be dehydrated with a drying agent such as sodium sulfate and magnesium sulfate, but this is not essential.

(883) The reaction mixture obtained above which contains the compound represented by Formula (1-u) may be distilled under reduced pressure to remove the solvent as long as the compound is not decomposed.

(884) The reaction mixture obtained after distillation of the solvent which contains the compound represented by Formula (1-u) may be purified by washing, reprecipitation, recrystallization, column chromatography and the like, using a suitable solvent. It may be optionally set in accordance with the desired purity.

(885) [Production Method AC]

(886) ##STR03507##

(887) In the formula, R2f represents a halogen atom, and HalR, R1, Het, X and Y are the same as defined hereinabove.

(888) Production Method AC is a method of obtaining a compound represented by Formula (1a-h), which belongs to the compounds represented by Formula (1a), wherein R2f is a halogen atom, and is a production method which comprises reacting a compound represented by Formula (1a-g) using a radical initiator and a halogenating agent (HalR) in a solvent.

(889) In Formula (1a-h), preferable R2f is a chlorine atom, a bromine atom or an iodine atom.

(890) The radical initiator to be used in the present reaction may include azobisisobutyronitrile, 2,2′-azobis(4-methoxy-2,4-dimethylvaleryonitrile), benzoyl peroxide and the like.

(891) An amount of the radical initiator to be used in the present reaction is not particularly limited as long as the target reaction proceeds, and is usually 0.01 equivalent or more and 1.0 equivalent or less relative to the compound represented by Formula (1a-g).

(892) The halogenating agent to be used in the present reaction may include N-chlorosuccinimide, N-bromosuccinimide, N-iodosuccinimide, 1,3-dichloro-5,5-dimethylhydantoin, 1,3-dibromo-5,5-dimethylhydantoin, 1,3-diiodo-5,5-dimethylhydantoin and the like.

(893) An amount of the halogenating agent to be used in the present reaction may be 2 equivalents or more relative to the compound represented by Formula (1a-g), which is not particularly limited as long as the target reaction proceeds, and is usually 2 equivalents or more and 2.8 equivalents or less.

(894) The solvent to be used in the present reaction is not particularly limited as long as the target reaction proceeds, and may include halogenated benzene solvents such as chlorobenzene and dichlorobenzene, ester solvents such as ethyl acetate, isopropyl acetate and butyl acetate, halogen based solvents such as dichloromethane, dichloroethane, chloroform and carbon tetrachloride, hydrocarbon solvents such as hexane, heptane, cyclohexane and methylcyclohexane, and the like. These solvents may be used singly, or two or more kinds may be used in combination in an optional ratio.

(895) An amount of the solvent to be used in the present reaction is not particularly limited as long as the target reaction proceeds, and is usually 3 times by weight or more and 200 times by weight or less relative to the compound represented by Formula (1a-g).

(896) A temperature to carry out the present reaction is not particularly limited as long as the target reaction proceeds, and is usually 20° C. or higher and 150° C. or lower or a boiling point of the solvent or lower.

(897) As a post treatment after the reaction, it is possible to carry out a liquid separating operation by adding water or a suitable aqueous solution to the reaction mixture. When an aqueous solution is to be used, an acidic aqueous solution in which hydrochloric acid, sulfuric acid, ammonium chloride or the like is dissolved, an alkaline aqueous solution in which potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate or the like is dissolved, an aqueous solution in which a salt containing a sulfur atom such as sodium thiosulfate, sodium sulfite or the like is dissolved or a saline solution or the like can be optionally used. At the time of the liquid separating operation, if necessary, it is possible to add a solvent which is immiscible with water including benzene based solvents such as toluene, xylene, benzene, chlorobenzene and dichlorobenzene, ester solvents such as ethyl acetate, isopropyl acetate and butyl acetate, ether solvents such as diethyl ether, diisopropyl ether and methyl-t-butyl ether, halogen based solvents such as dichloromethane, dichloroethane and chloroform, hydrocarbon solvents such as hexane, heptane, cyclohexane and methylcyclohexane, and the like. In addition, it is possible to use these solvents singly or to mix two or more kinds with an optional ratio. The number of times of the liquid separation is not particularly limited, and may be carried out in accordance with the purity and yield to be desired.

(898) The reaction mixture obtained above which contains the compound represented by Formula (1a-h) may be dehydrated with a drying agent such as sodium sulfate and magnesium sulfate, but this is not essential.

(899) The reaction mixture obtained above which contains the compound represented by Formula (1a-h) may be distilled under reduced pressure to remove the solvent as long as the compound is not decomposed.

(900) The reaction mixture obtained after distillation of the solvent which contains the compound represented by Formula (1a-h) may be purified by washing, reprecipitation, recrystallization, column chromatography and the like, using a suitable solvent. It may be optionally set in accordance with the desired purity.

(901) [Production Method AD]

(902) ##STR03508##

(903) In the formula, R1, R2f, Het, X and Y are the same as defined hereinabove.

(904) Production Method AD is a method of obtaining a compound represented by Formula (1a-i) which belongs to the compounds represented by Formula (1a), and is a production method which comprises hydrolyzing a compound represented by Formula (1a-h) in the presence of water in a solvent.

(905) In Formula (1a-h), preferable R2f is a chlorine atom, a bromine atom or an iodine atom.

(906) In the present reaction, water is essential. Also, in order to proceed the present reaction smoothly, silver nitrate may be used.

(907) When an amount of water to be used in the present reaction is 1 equivalent or more relative to the compound represented by Formula (1a-h), it is not limited as long as the target reaction proceeds. In addition, water can be used as a solvent.

(908) When an amount of the silver nitrate to be used in the present reaction is 2 equivalents or more relative to the compound represented by Formula (1a-h), it is not limited as long as the target reaction proceeds, and it is usually 2 equivalents or more and 10 equivalents or less.

(909) The solvent to be used in the present reaction is not particularly limited as long as the target reaction proceeds, and may include water solvent, ether solvents such as diethyl ether, diisopropyl ether, methyl-t-butyl ether, dimethoxyethane, tetrahydrofuran and dioxane, nitrile solvents such as acetonitrile, and the like. These solvents may be used singly, or two or more kinds may be used in combination in an optional ratio.

(910) An amount of the solvent to be used in the present reaction is not particularly limited as long as the target reaction proceeds, and is usually 3 times by weight or more and 200 times by weight or less relative to the compound represented by Formula (1a-h).

(911) A temperature to carry out the present reaction is not particularly limited as long as the target reaction proceeds, and is usually −10° C. or higher and 100° C. or lower or a boiling point of the solvent or lower.

(912) As a post treatment after the reaction, it is possible to remove undissolved metal by filtration. Further, it is possible to carry out a liquid separating operation by adding water or a suitable aqueous solution to the reaction mixture. When an aqueous solution is to be used, an acidic aqueous solution in which hydrochloric acid, sulfuric acid, ammonium chloride or the like is dissolved, an alkaline aqueous solution in which potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate or the like is dissolved, an aqueous solution in which a salt containing a sulfur atom such as sodium thiosulfate, sodium sulfite or the like is dissolved or a saline solution or the like can be optionally used. At the time of the liquid separating operation, if necessary, it is possible to add a solvent which is immiscible with water including benzene based solvents such as toluene, xylene, benzene, chlorobenzene and dichlorobenzene, ester solvents such as ethyl acetate, isopropyl acetate and butyl acetate, ether solvents such as diethyl ether, diisopropyl ether and methyl-t-butyl ether, halogen based solvents such as dichloromethane, dichloroethane, chloroform and carbon tetrachloride, hydrocarbon solvents such as hexane, heptane, cyclohexane and methylcyclohexane, and the like. In addition, it is possible to use these solvents singly or to mix two or more kinds with an optional ratio. The number of times of the liquid separation is not particularly limited, and may be carried out in accordance with the purity and yield to be desired.

(913) The reaction mixture obtained above which contains the compound represented by Formula (1a-i) may be dehydrated with a drying agent such as sodium sulfate and magnesium sulfate, but this is not essential.

(914) The reaction mixture obtained above which contains the compound represented by Formula (1a-i) may be distilled under reduced pressure to remove the solvent as long as the compound is not decomposed.

(915) The reaction mixture obtained after distillation of the solvent which contains the compound represented by Formula (1a-i) may be purified by washing, reprecipitation, recrystallization, column chromatography and the like, using a suitable solvent. It may be optionally set in accordance with the desired purity.

(916) [Production Method AE]

(917) ##STR03509##

(918) In the formula, FR represents a fluorinating agent, and R1, Het, X and Y are the same as defined hereinabove.

(919) Production Method AE is a method of obtaining a compound represented by Formula (1a-j) having a fluorine atom which belongs to the compounds represented by Formula (1a), and is a production method which comprises reacting a compound represented by Formula (1a-i) and a fluorinating agent (FR) in a solvent.

(920) The fluorinating agent to be used in the present reaction may include (diethylamino)sulfur trifluoride, bis(2-methoxyethyl)aminosulfur trifluoride, N,N-diethyl-1,1,2,3,3,3-hexafluoropropylamine, 2,2-difluoro-1,3-dimethylimidazolidine and the like.

(921) An amount of the fluorinating agent to be used in the present reaction may be 2 equivalents or more relative to the compound represented by Formula (1a-i), which is not particularly limited as long as the target reaction proceeds, and is usually 2 equivalents or more and 10 equivalents or less.

(922) The solvent to be used in the present reaction is not particularly limited as long as the target reaction proceeds, and may include ether solvents such as diethyl ether, diisopropyl ether, methyl-t-butyl ether, dimethoxyethane, tetrahydrofuran and dioxane, benzene based solvents such as benzene, toluene, xylene, mesitylene, chlorobenzene and dichlorobenzene, nitrile solvents such as acetonitrile, halogen based solvents such as dichloromethane, dichloroethane, chloroform and carbon tetrachloride, hydrocarbon solvents such as hexane, heptane, cyclohexane and methylcyclohexane, and the like. These solvents may be used singly, or two or more kinds may be used in combination in an optional ratio.

(923) An amount of the solvent to be used in the present reaction is not particularly limited as long as the target reaction proceeds, and is usually 3 times by weight or more and 200 times by weight or less relative to the compound represented by Formula (1a-i).

(924) A temperature to carry out the present reaction is not particularly limited as long as the target reaction proceeds, and is usually −80° C. or higher and 100° C. or lower or a boiling point of the solvent or lower.

(925) As a post treatment after the reaction, it is possible to carry out a liquid separating operation by adding water or a suitable aqueous solution to the reaction mixture. When an aqueous solution is to be used, an acidic aqueous solution in which hydrochloric acid, sulfuric acid, ammonium chloride or the like is dissolved, an alkaline aqueous solution in which potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate or the like is dissolved, an aqueous solution in which a salt containing a sulfur atom such as sodium thiosulfate, sodium sulfite or the like is dissolved or a saline solution or the like can be optionally used. At the time of the liquid separating operation, if necessary, it is possible to add a solvent which is immiscible with water including benzene based solvents such as toluene, xylene, benzene, chlorobenzene and dichlorobenzene, ester solvents such as ethyl acetate, isopropyl acetate and butyl acetate, ether solvents such as diethyl ether, diisopropyl ether and methyl-t-butyl ether, halogen based solvents such as dichloromethane, dichloroethane, chloroform and carbon tetrachloride, hydrocarbon solvents such as hexane, heptane, cyclohexane and methylcyclohexane, and the like. In addition, it is possible to use these solvents singly or to mix two or more kinds with an optional ratio. The number of times of the liquid separation is not particularly limited, and may be carried out in accordance with the purity and yield to be desired.

(926) The reaction mixture obtained above which contains the compound represented by Formula (1a-j) may be dehydrated with a drying agent such as sodium sulfate and magnesium sulfate, but this is not essential.

(927) The reaction mixture obtained above which contains the compound represented by Formula (1a-j) may be distilled under reduced pressure to remove the solvent as long as the compound is not decomposed.

(928) The reaction mixture obtained after distillation of the solvent which contains the compound represented by Formula (1a-j) may be purified by washing, reprecipitation, recrystallization, column chromatography and the like, using a suitable solvent. It may be optionally set in accordance with the desired purity.

(929) [Production Method AF]

(930) ##STR03510##

(931) In the formula, Ox represents an oxidizing agent, and R2, Het, X and Y are the same as defined hereinabove.

(932) Production Method AF is a method of obtaining a compound represented by Formula (2-a), and is a production method which comprises reacting a compound represented by Formula (2) and an oxidizing agent (Ox) in a solvent.

(933) By using the compound represented by Formula (2) in place of the compound represented by Formula (1b) in Production Method E, Production Method AF can be carried out in accordance with Production Method E.

(934) [Production Method AG]

(935) ##STR03511##

(936) In the formula, R2b represents a halogen atom, HalR represents a halogenating agent, and Het, X and Y are the same as defined hereinabove.

(937) Production Method AG is a production method of obtaining a compound represented by Formula (2-c), which belongs to the compounds represented by Formula (2-a), wherein R2b represents a halogen atom, and is a production method which comprises reacting a compound represented by Formula (2-b) and a halogenating agent (HalR) in a solvent.

(938) By using the compound represented by Formula (2-b) in place of the compound represented by Formula (1a-a) in Production Method F, Production Method AG can be carried out in accordance with Production Method F.

(939) [Production Method AH]

(940) ##STR03512##

(941) In the formula, RNH.sub.2 represents an aminating agent, and R2, Het, X and Y are the same as defined hereinabove.

(942) Production Method AH is a method of obtaining a compound represented by Formula (2-d), and is a production method which comprises a compound represented by Formula (2-a) and an aminating agent (RNH.sub.2) in the presence of a base in a solvent.

(943) The aminating agent to be used in the present reaction may include diphenyl-phosphineamide, O-(4-nitrobenzoyl)hydroxylamine, O-(2,4-dinitrophenyl)-hydroxylamine, O-(diphenylphosphinyl)hydroxylamine and the like.

(944) An amount of the aminating agent to be used in the present reaction may be 1 equivalent or more relative to the compound represented by Formula (2-a), which is not particularly limited as long as the target reaction proceeds, and is usually 1 equivalent or more and 5 equivalents or less.

(945) The base to be used in the present reaction may be exemplified by inorganic bases such as lithium hydroxide, sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, cesium carbonate and tripotassium phosphate, metal alkoxides such as sodium methoxide, sodium ethoxide and potassium t-butoxide, metal hydrides such as sodium hydride, and metal amides such as lithium diisopropylamide, hexamethyldisilazane lithium, hexamethyldisilazane sodium and hexamethyldisilazane potassium, and is not particularly limited as long as the target reaction proceeds.

(946) An amount of the base to be used in the present reaction a base may be 1 equivalent or more relative to the compound represented by Formula (2-a), which is not particularly limited as long as the target reaction proceeds, and preferably 1 equivalent or more and 10 equivalents or less.

(947) The solvent to be used in the present reaction is not particularly limited as long as the target reaction proceeds, and may include ether solvents such as diethyl ether, diisopropyl ether, methyl-t-butyl ether, dimethoxyethane, tetrahydrofuran and dioxane, benzene based solvents such as benzene, toluene, xylene, mesitylene, chlorobenzene and dichlorobenzene, nitrile solvents such as acetonitrile, halogen based solvents such as dichloromethane, dichloroethane, chloroform and carbon tetrachloride, amide solvents such as N-methylpyrrolidone, N,N-dimethylformamide and N,N-dimethylacetamide, urea solvents such as 1,3-dimethyl-2-imidazolidinone, hydrocarbon solvents such as hexane, heptane, cyclohexane and methylcyclohexane, and the like. These solvents may be used singly, or two or more kinds may be used in combination in an optional ratio.

(948) An amount of the solvent to be used in the present reaction is not particularly limited as long as the target reaction proceeds, and is usually 3 times by weight or more and 200 times by weight or less relative to the compound represented by Formula (2-a).

(949) A temperature to carry out the present reaction is not particularly limited as long as the target reaction proceeds, and is usually −80° C. or higher and 100° C. or lower or a boiling point of the solvent or lower.

(950) As a post treatment after the reaction, it is possible to carry out a liquid separating operation by adding water or a suitable aqueous solution to the reaction mixture. When an aqueous solution is to be used, an acidic aqueous solution in which hydrochloric acid, sulfuric acid, ammonium chloride or the like is dissolved, an alkaline aqueous solution in which potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate or the like is dissolved, an aqueous solution in which a salt containing a sulfur atom such as sodium thiosulfate, sodium sulfite or the like is dissolved or a saline solution or the like can be optionally used. At the time of the liquid separating operation, if necessary, it is possible to add a solvent which is immiscible with water including benzene based solvents such as toluene, xylene, benzene, chlorobenzene and dichlorobenzene, ester solvents such as ethyl acetate, isopropyl acetate and butyl acetate, ether solvents such as diethyl ether, diisopropyl ether and methyl-t-butyl ether, halogen based solvents such as dichloromethane, dichloroethane, chloroform and carbon tetrachloride, hydrocarbon solvents such as hexane, heptane, cyclohexane and methylcyclohexane, and the like. In addition, it is possible to use these solvents singly or to mix two or more kinds with an optional ratio. The number of times of the liquid separation is not particularly limited, and may be carried out in accordance with the purity and yield to be desired.

(951) The reaction mixture obtained above which contains the compound represented by Formula (2-d) may be dehydrated with a drying agent such as sodium sulfate and magnesium sulfate, but this is not essential.

(952) The reaction mixture obtained above which contains the compound represented by Formula (2-d) may be distilled under reduced pressure to remove the solvent as long as, the compound is not decomposed.

(953) The reaction mixture obtained after distillation of the solvent which contains the compound represented by Formula (2-d) may be purified by washing, reprecipitation, recrystallization, column chromatography and the like, using a suitable solvent. It may be optionally set in accordance with the desired purity.

(954) [Production Method AI]

(955) ##STR03513##

(956) In the formula, Raa represents a C1-C6 alkyl group optionally substituted with substituent(s) B, a C1-C6 haloalkyl group or a C3-C8 cycloalkyl group, and R2, Het, Lv, X and Y are the same as defined hereinabove.

(957) Production Method AI is a method of obtaining a compound represented by Formula (2-e), and is a production method which comprises reacting a compound represented by Formula (2-d) and Raa-Lv in the presence of a base in a solvent.

(958) The Raa-Lv to be used in the present reaction can be obtained as a commercially available product or produced by a conventionally known method.

(959) An amount of the Raa-Lv to be used in the present reaction may be 1 equivalent or more relative to the compound represented by Formula (2-d), which is not particularly limited as long as the target reaction proceeds, and preferably 1 equivalent or more and 10 equivalents or less.

(960) The base to be used in the present reaction may be exemplified by inorganic bases such as sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, cesium carbonate and sodium hydride, and is not particularly limited as long as the target reaction proceeds.

(961) An amount of the base to be used in the present reaction may be 1 equivalent or more relative to the compound represented by Formula (2-d), which is not particularly limited as long as the target reaction proceeds, and preferably 1 equivalent or more and 10 equivalents or less.

(962) The solvent to be used in the present reaction is not particularly limited as long as the target reaction proceeds, and may include ether solvents such as diethyl ether, diisopropyl ether, methyl-t-butyl ether, dimethoxyethane, tetrahydrofuran and dioxane, alcohol solvents such as methanol, ethanol and isopropanol, benzene based solvents such as benzene, toluene, xylene, mesitylene, chlorobenzene and dichlorobenzene, ester solvents such as ethyl acetate, isopropyl acetate and butyl acetate, nitrile solvents such as acetonitrile, amide solvents such as N-methylpyrrolidone, N,N-dimethylformamide and N,N-dimethylacetamide, urea solvents such as 1,3-dimethyl-2-imidazolidinone, halogen based solvents such as dichloromethane, dichloroethane, chloroform and carbon tetrachloride, sulfur solvents such as dimethylsulfoxide and sulforane, ketone solvents such as acetone, methyl ethyl ketone and methyl isobutyl ketone and water solvent, and the like. These solvents may be used singly, or two or more kinds may be used in combination in an optional ratio.

(963) An amount of the solvent to be used in the present reaction is not particularly limited as long as the target reaction proceeds, and is usually 3 times by weight or more and 200 times by weight or less relative to the compound represented by Formula (2-d).

(964) A temperature to carry out the present reaction is not particularly limited as long as the target reaction proceeds, and is usually 0° C. or higher and 150° C. or lower or a boiling point of the solvent or lower.

(965) As a post treatment after the reaction, it is possible to carry out a liquid separating operation by adding water or a suitable aqueous solution to the reaction mixture. When an aqueous solution is to be used, an acidic aqueous solution in which hydrochloric acid, sulfuric acid, ammonium chloride or the like is dissolved, an alkaline aqueous solution in which potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate or the like is dissolved, an aqueous solution in which a salt containing a sulfur atom such as sodium thiosulfate, sodium sulfite or the like is dissolved or a saline solution or the like can be optionally used. At the time of the liquid separating operation, if necessary, it is possible to add a solvent which is immiscible with water including benzene based solvents such as toluene, xylene, benzene, chlorobenzene and dichlorobenzene, ester solvents such as ethyl acetate, isopropyl acetate and butyl acetate, ether solvents such as diethyl ether, diisopropyl ether and methyl-t-butyl ether, halogen based solvents such as dichloromethane, dichloroethane, chloroform and carbon tetrachloride, hydrocarbon solvents such as hexane, heptane, cyclohexane and methylcyclohexane, and the like. In addition, it is possible to use these solvents singly or to mix two or more kinds with an optional ratio. The number of times of the liquid separation is not particularly limited, and may be carried out in accordance with the purity and yield to be desired.

(966) The reaction mixture obtained above which contains the compound represented by Formula (2-e) may be dehydrated with a drying agent such as sodium sulfate and magnesium sulfate, but this is not essential.

(967) The reaction mixture obtained above which contains the compound represented by Formula (2-e) may be distilled under reduced pressure to remove the solvent as long as the compound is not decomposed.

(968) The reaction mixture obtained after distillation of the solvent which contains the compound represented by Formula (2-e) may be purified by washing, reprecipitation, recrystallization, column chromatography and the like, using a suitable solvent. It may be optionally set in accordance with the desired purity.

(969) [Production Method AJ]

(970) ##STR03514##

(971) In the formula, Rba represents a C1-C6 alkyl group optionally substituted with substituent(s) B, a C1-C6 haloalkyl group or a C3-C8 cycloalkyl group, and R2, Het, Lv, X and Y are the same as defined hereinabove.

(972) Production Method AJ is a method of obtaining a compound represented by Formula (2-f), and is a production method which comprises reacting a compound represented by Formula (2-e) and Rba-Lv in the presence of a base in a solvent.

(973) The Rba-Lv to be used in the present reaction can be obtained as a commercially available product or produced by a conventionally known method.

(974) By using the compound represented by Formula (2-e) in place of the compound represented by Formula (2-d) in Production Method AI, Production Method AJ can be carried out in accordance with Production Method AI. Also, when Raa and Rba are the same, by using 2 equivalents or more of Raa-Lv relative to Formula (2-d) in Production Method AI, the compound represented by Formula (2-f) can be synthesized.

(975) The compounds represented by Formula (1) can be produced by optionally combining Production Method A to Production Method AJ shown hereinabove. Or else, the compounds represented by Formula (1) can be produced even when the conventionally known method and Production Method A to Production Method AJ are optionally combined.

(976) The compounds of the present invention can protect plants from harmful organisms and thus may be used as agricultural chemicals. Specifically, examples thereof includes fungicides, insecticides, herbicides, plant growth regulators and the like. It is preferably fungicides.

(977) The compounds of the present invention can be used as an agricultural and horticultural fungicide in farms, paddy fields, tea gardens, orchards, meadows, grasses, forests, gardens, roadside trees, etc., for prevention and treatment of plant diseases.

(978) Plant diseases referred to in the present invention mean that systemic, abnormal pathological symptoms such as wilting, damping-off, yellowing, dwarfism, and spindly growth, or partial pathological symptoms such as spotting, leaf blight, mosaic pattern, leaf rolling, die back, root rot, club root, and knotting are induced in plants such as crops, flowering plants, flowering trees and shrubs, and trees. That is, the plants are to get sick. As pathogens that cause plant diseases, there may be mainly mentioned fungi, bacteria, spiroplasmas, phytoplasmas, viruses, viroids, parasitic higher plants, nematodes and the like. The compounds of the present invention are effective against fungi, but it is not limited thereto.

(979) Diseases caused by fungi are mainly fungal diseases. Examples of fungi (pathogens) that cause fungal diseases include Plasmodiophora, Oomycetes, Zygomycetes, Ascomycetes, Basidiomycetes and Deuteromycetes. For example, Plasmodiophora may include club root fungus, potato powdery scab fungus and beet necrotic yellow vein virus, Oomycetes may include blight fungus, downy mildew fungus, Pythium species fungus and Aphanomyces species fungus, Zygomycetes may include Rhizopus species fungus, Ascomycetes may include peach leaf curl fungus, corn brown spot fungus, rice blast fungus, powdery mildew fungus, anthracnose fungus, Fusarium head blight fungus, bakanae disease fungus and sclerotial disease fungus, Basidiomycetes may include rust disease fungus, smut fungus, violet root rot fungus, blister blight fungus and rice sheath blight fungus, and Deuteromycetes may include gray mold fungus, Alternaria species fungus, Fusarium species fungus, Penicillium species fungus, Rhizoctonia species fungus, southern blight fungus and the like.

(980) The compounds of the present invention are effective against various plant diseases. The following provides specific examples of disease names and pathogens thereof.

(981) Rice: blast (Magnaporthe grisea), sheath blight (Thanatephorus cucumeris), brown sclerotial disease (Ceratobasidium setariae), small sclerotial disease (Waitea circinata), brown sheath blight (Thanatephorus cucumeris), globular sclerotial disease (Sclerotium hydrophilum), red sclerotial disease (Wairea circinata), black leaf blight (Entyloma dactylidis), stem rot (Magnaporthe salvinii), gray sclerotial disease (Ceratobasidium cornigerum), brown spot (Cochliobolus miyabeanus), Cercospora leaf spot (Sphaerulina oryzina), bakanae disease (Gibberella fujikuroi), seedling damping-off (Pythium spp., Fusarium spp., Trichoderma spp., Rhizopus spp., Rhizoctonia solani, Mucor sp., Phoma sp.), seedling rot (Pythium spp., Achlya spp., Dictyuchus spp.), rice false smut (Claviceps virens), kernel smut (Tilletia barclayana), discolored rice grains (Curvularia spp., Alternaria spp.), crazy top (Sclerophthora macrospora), bacterial leaf blight (Xanthomonas oryzae pv. oryzae), bacterial brown stripe (Acidovorax avenae subsp. avenae), bacterial palea browning (Erwinia ananas), bacterial seedling damping-off (Burkholderia plantarii), bacterial grain rot (Burkholderia glumae), sheath brown rot (Pseudomonas fuscovaginae), bacterial halo blight (Pseudomonas syringae pv. oryzae), bacterial foot rot (Erwinia chrysanthemi), yellow dwarf (Phytoplasma oryzae), rice stripe (Rice stripe tenuivirus), rice dwarf (Rice dwarf reovirus);

(982) wheat and barley: powdery mildew (Blumeria graminis fsp. hordei; fsp. tritici), rust (Puccinia striiformis, Puccinia graminis, Puccinia recondita, Puccinia hordei), barley stripe (Pyrenophora graminea), net blotch (Pyrenophora teres), Fusarium head blight (Gibberella zeae, Fusarium culmorum, Fusarium avenaceum, Monographella nivalis), Typhula snow blight (Typhula incarnata, Typhula ishikariensis, Monographella nivalis), loose kernel smut (Ustilago nuda), stinking smut (Tilletia caries, Tilletia controversa), eye spot (Pseudocercosporella herpotrichoides), foot rot (Ceratobasidium gramineum), leaf scald (Rhynchosporium secalis), speckled leaf blotch (Septoria tritici), glume blotch (Phaeosphaeria nodorum), damping-off (Fusarium spp., Pythium spp., Rhizoctonia spp., Septoria spp., Pyrenophora spp.), seedling blight (Gaeumannomyces graminis), anthracnose (Colletotrichum graminicola), ergot (Claviceps purpurea), leaf spot (Cochliobolus sativus), bacterial black node (Pseudoronas syringae pv. syringae);
corn: leaf rust (Gibberella zeae, etc.), damping-off (Fusarium avenaceum, Penicillium spp., Pythium spp., Rhizoctonia spp.), rust (Puccinia sorghi), brown spot (Cochliobolus heterostrophus), loose smut (Ustilago maydis), anthracnose (Colletotrichum graminicola), northern leaf spot (Cochliobolus carbonum), bacterial brown stripe (Acidovorax avenae subsp. avenae), bacterial stripe (Burkholderia andropogonis), bacterial stalk rot (Erwinia chrysanthemi pv. zeae), bacterial wilt (Erwinia stewartii); grapes: downy mildew (Plasmopara viticola), rust (Physopella ampelopsidis), powdery mildew (Uncinula necator), scab (Elsinoe amnpelina), ripe rot (Glomerella cingulata, Colletotrichum acutatum), black rot (Guignardia bidwellii), Phomopsis leaf spot (Phomopsis viticola), fly speck (Zygophiala jamaicensis), gray mold (Botrytis cinerea), twig blight (Diaporthe medusaea), violet root rot (Helicobasidium mompa), white root rot (Rosellinia necatrix), crown gall (Agrobacterium vitis); apples: powdery mildew (Podosphaera leucotricha), black spot disease (Venturia inaequalis), Alternaria leaf spot (Alternaria mali), rust (Gymnosporangium yamadae), blossom blight (Monilinia mali), apple canker (Valsa ceratosperma), ring spot (Botyosphaeria berengeriana), anthracnose (Colletotrichurn acutatum, Glomerella cingulata), fly speck (Zygophiala jamaicensis), sooty spot (Gloeodes pomigena), fruit spot (Mycosphaerella pomi), violet root rot (Helicobasidium mompa), white root rot (Rosellinia necatrix), canker (Phomopsis mali, Diaporthe tanakae), apple blotch (Diplocarpon mali), fire blight (Erwinia amylovora), crown gall (Agrobacterium tumefaciens), hairy root disease (Agrobacterium rhizogenes);
Japanese pears: black spot (Alternaria kikuchiana), pear scab (Venturia nashicola), rust (Gymnosporangium asiaticum), ring spot (Botryosphaeria berengeriana fsp. piricola), pear canker (Phomopsis fukushii), bacterial shoot blight (Erwinia sp.), crown gall (Agrobacterium tumefaciens), rusty canker (Erwinia chrysanthemi pv. chrysanthemi), bacterial petal blight (Pseudomonas syringae pv. syringae); European pears: blight (Phytophthora cactorum, Phytophthora syringae), bacterial shoot blight (Erwinia sp.); peaches: black spot (Cladosporium carpophilum), Phomopsis rot (Phomopsis sp.), blight (Phytophthora sp.), anthracnose (Colletotrichum gloeosporioides), leaf curl (Taphrina deformans), bacterial shot hole (Xhanthomonas campestris pv. pruni), crown gall (Agrobacterium tumefaciens); cherries: anthracnose (Glomerella cingulata), young fruit sclerotial disease (Monilinia kusanoi), gray spot (Monilinia fructicola), crown gall (Agrobacterium tumefaciens), bacterial gummosis. (Pseudomonas syringae pv. syringae); persimmons: anthracnose (Glomerella cingulata), brown stem rot (Cercospora kaki; Mycosphaerella nawae), powdery mildew (Phyllactinia kakikora), crown gall (Agrobacterium tumefaciens); citrus fruits: melanose (Diaporthe citri), green mold disease (Penicillium digitatum), blue mold disease (Penicillium italicum), scab (Elsinoe fawcettii), brown rot (Phytophthora citrophthora), canker (Xhanthomonas campestris pv. citri), bacterial brown spot (Pseudomonas syringae pv. syringae), greening disease (Liberibactor asiaticus), crown gall (Agrobacterium tumefaciens); tomato, cucumbers, beans, strawberries, potatoes, cabbage, eggplants, lettuce and the like: gray mold (Botrytis cinerea); tomatoes, cucumbers, beans, strawberries, potatoes, rapeseed, cabbage, eggplants, lettuce and the like: sclerotial disease (Sclerotinia sclerotiorum); various vegetables such as tomatoes, cucumbers, beans, radishes, watermelons, eggplants, rapeseed, green peppers, spinach, beets and the like: seedling damping-off (Rhizoctonia spp., Pythium spp., Fusarium spp., Phythophthora spp., Sclerotinia sclerotiorum, etc.); solanaceous plants: bacterial wilt (Ralstonia solanacearum); melons: downy mildew (Pseudoperonospora cubensis), powdery mildew (Sphaerotheca fuliginea), anthracnose (Colletotrichum orbiculare), gummy stem blight (Didymella bryoniae), stem rot (Fusarium oxysporum), late blight (Phytophthora parasitica, Phytophthora melonis, Phytophthora nicotianae, Phytophthora drechsleri, Phytophthora capsici, etc.), bacterial brown spot (Xhanthomonas campestris pv. cucurbitae), soft rot (Erwinia carotovora subsp. carotovora), bacterial spot (Pseudomonas syringae pv. lachrymans), marginal blight (Pseudomonas marginalis pv. marginalis), canker (Streptomyces sp.), hairy root disease (Agrobacterium rhizogenes), cucumber mosaic virus (Cucumber mosaic virus);
tomatoes: ring spot (Alternaria solani), leaf mold (Fulvia fulva), late blight (Phytophthora infestans), wilt disease (Fusarium oxysporum), root rot (Pythium myriotylum, Pythium dissotocum), anthracnose (Colletotrichum gloeosporioides), canker (Clavibacter michiganensis), pith necrosis (Pseudomonas corrugata), bacterial black spot (Pseudomonas viridiflava), soft rot (Erwinia carotovora subsp. carotovora), bacterial leaf gall (Crynebacterium sp.), yellowing wilt (Phytoplasma asteris), yellow dwarfism (Tobacco leaf curl subgroup III geminivirus); eggplants: powdery mildew (Sphaerotheca fidiginea, etc.), leaf mold (Mycovellosiella nattrassii), blight (Phytophthora infestans), brown rot (Phytophthora capsici), bacterial brown spot (Pseudomonas cichorii), necrotic leaf spot (Pseudomonas corrugata), bacterial stem rot (Erwinia chrysantherni), soft rot (Erwinia carotovora subsp. carotovora), bacterial spot (Pseudomonas sp.); rapeseed: black spot (Alternaria brassicae), black rot (Xhanthomonas campestris pv. campestris), bacterial black spot (Pseudomonas syringae pv. maculicola), soft rot (Erwinia carotovora); cruciferous vegetables: black spot (Alternaria brassicae, etc.), white spot (Cercosporella brassicae), black leg (Phoma lingam), club root (Plasmodiophora brassicae), downy mildew (Peronospora parasitica), black rot (Xhanthomonas campestris pv. campestris), bacterial black spot (Pseudomonas syringae pv. maculicola), soft rot (Erwinia carotovora subsp. carotovora);
cabbage: club foot (Thanatephorus cucumeris), yellowing wilt (Fusarium oxysporum), alternaria sooty spot (Alternaria brassisicola); Chinese cabbage: bottom rot (Rhizoctonia solani), yellowing (Verticillium dahliae); green onions: rust (Puccinia allii), black spot (Alternaria porri), southern blight (Sclerotium rolfsii), white rot (Phytophthora porri), black rot (Sclerotium cepivorum); onions: canker (Curtobacterium flaccumfaciens), soft rot (Erwinia carotovora subsp. carotovora), bacterial spot (Pseudomonas syringae pv. syringae), rot (Erwinia rhapontici), scale rot (Burkholderia gladioli), yellowing wilt (Phytoplasma asteris); garlic: soft rot (Erwinia carotovora subsp. carotovora), spring rot (Pseudomonas marginalis pv. marginalis); soybeans: purple seed stain (Cercospora kikuchii), scab (Elsinoe glycines), black spot (Diaporthe phaseolorum), Rhizoctonia root rot (Rhizoctonia solani), stem rot (Phytophthora sojae), downy mildew (Peronospora manshurica), rust (Phakopsora pachyrhizi), anthracnose (Colletotrichum truncatum, etc.), leaf scald (Xhanthomonas campestris pv. glycines), bacterial spot (Pseudomonas syringae pv. glycinea); green beans: anthracnose (Colletotrichum lindemuthianum), bacterial wilt (Ralstonia solanacearum), halo blight (Pseudomonas syringae pv. phaseolicola), bacterial brown spot (Pseudomonas viridiflava), leaf scald (Xhanthomonas campestris pv. phaseoli); peanuts: leaf spot (Mycosphaerella berkeleyi), brown spot (Mycosphaerella arachidis), bacterial wilt (Ralstonia solanacearum); peas: powdery mildew (Erysiphe pisi), downy mildew (Peronospora pisi), bacterial stem blight (Pseudomonas syringae pv. pisi), bacterial stem rot (Xhanthomonas campestris pv. pisi); broad beans: downy mildew (Peronospora viciae), blight (Phytophthora nicotianae); potatoes: early blight (Alternaria solani), black scurf (Thanatephorus cucumeris), blight (Phytophthora infestans), silver scurf (Helminthosporium solani), soft rot (Fusarium oxysporum, Fusarium solani), powdery scab (Spongospora subterranea), bacterial wilt (Ralstonia solanacearum), black foot disease (Erwinia carotovora subsp. atroseptica), common scab (Streptomyces scabies, Streptomyces acidiscabies), soft rot (Erwinia carotovora subsp. carotovora), slimy rot (Crostridium spp.), ring rot (Clavibacter michiganensis subsp. sepedonicus); sweet potatoes: damping-off (Streptomyces ipomoeae); beets: brown spot (Cercospora beticola), downy mildew (Peronospora schachtii), black root rot (Aphanomyces cochioides), leaf spot (Phoma betae), crown gall (Agrobacterium tumefaciens), scab (Streptomyces scabies), bacterial spot (Pseudomonas syringae pv. aptata);
carrots: leaf blight (Alternaria dauci), bacterial gall (Rhizobacter dauci), crown gall (Agrobacterium tumefaciens), Streptomyces scab (Streptomyces spp.), soft rot (Erwinia carotovora subsp. carotovora); strawberries: powdery mildew (Sphaerotheca aphanis var. aphanis), blight (Phytophthora nicotianae, etc.), anthracnose (Glomerella cingulata, etc.), fruit rot (Pythium ultimum), bacterial wilt (Ralstonia solanacearum), angular leaf spot (Xhanthomonas campestris), bacterial bud blight (Pseudomonas marginalis pv. marginalis); tea: net blister blight (Exobasidium reticulatum), white scab (Elsinoe leucospila), anthracnose (Colletotrichum theae-sinensis), ring spot (Pestalotiopsis longiseta), red blight (Pseudomonas syringae pv. theae), canker (Xhanthomonas campestris pv. theicola), witch's broom (Pseudomonas sp.); tobacco: red spot (Alternaria alternata), powdery mildew (Erysiphe cichoracearum), anthracnose (Colletotrichum gloeosporioides), blight (Phytophthora nicotianae), wildfire (Pseudomonas syringae pv. tabaci), bacterial leaf spot (Pseudomonas syringae pv. mellea), hollow root (Erwinia carotovora subsp. carotovora), damping-off (Ralstonia solanacearum), tobacco mosaic virus (Tobacco mosaic virus);
coffee: rust disease (Hemileia vastatrix); banana: black sigatoka (Mycosphaerella fijiensis), panama disease (Fusarium oxysporum fsp cubense); cotton: damping-off (Fusarium oxysporum), frosty mildew (Ramularia areola); sunflowers: sclerotial disease (Sclerotinia sclerotiorum), angular leaf spot (Xhanthomonas campestris pv. malvacearum), hollow root (Erwinia carotovora subsp. carotovora), bacterial spot (Pseudomonas syringae pv. helianthi); roses: black spot (Diplocarpon rosae), powdery mildew (Sphaerotheca pannosa, etc.), blight (Phytophthora megasperma), downy mildew (Peronospora sparsa), crown gall (Agrobacterium tumefaciens); chrysanthemums: brown spot (Septoria obesa), white rust (Puccinia horiana), blight (Phytophthora cactorum), bacterial spot (Pseudomonas cichorii), soft rot (Erwinia carotovora subsp. carotovora), crown gall (Agrobacterium tumefaciens), hairy root disease (Agrobacterium rhizogenes), chrysanthemum virescence (Phytoplasma aurantifolia); grasses: brown patch disease (Rhizoctonia solani), dollar spot disease (Sclerotinia homoeocarpa), curvularia leaf blight (Curvularia sp.), rust (Puccinia zoysiae), helminthosporium leaf blight (Cochliobolus sp.), scald (Rhynchosporium secalis), damping-off (Gaeumannomyces graminis), anthracnose (Colletotrichum sp.), Typhula brown snow blight (Typhula incarnata), Typhula black snow blight (Typhula ishikariensis), Sclerotinia (Myriosclerotinia borealis), fairy ring disease (Marasmius oreades, etc.), Pythium blight (Pythium aphanidermatum, etc.), blast (Pyricularia grisea) and the like.