ACRYLATE DERIVATIVE, USE AND PRODUCTION INTERMEDIATE COMPOUND OF THE SAME

Abstract

The present invention provides a compound represented by formula (I) [wherein L represents an oxygen atom or CH.sub.2, E represents a C2-C10 chain hydrocarbon group or the like, R.sup.1 represents a C1-C3 chain hydrocarbon group or the like, R.sup.2 represents a C1-C3 chain hydrocarbon group or the like, and n is 0, 1, 2 or 3.] or its N oxide or agriculturally acceptable salt, which is a compound that have excellent pests controlling effects.

##STR00001##

Claims

1. A compound represented by formula (I): ##STR00159## [wherein, L represents an oxygen atom or CH.sub.2, E represents a methyl group which is substituted with one or more substituents selected from Group A, a C2-C10 chain hydrocarbon group which may be optionally substituted with one or more substituents selected from Group A, R.sup.6C(O)—, R.sup.4OC(O)—, R.sup.3R.sup.5NC(O)—, R.sup.3R.sup.5NC(S)—, R.sup.4S(O).sub.2—, or R.sup.3R.sup.5NS(O).sub.2—, R.sup.1 represents a C1-C3 chain hydrocarbon group which may be optionally substituted with one or more halogen atoms, a cyclopropyl group, or a halogen atom, n is 0, 1, 2 or 3, when n is 2 or 3, a plurality of R.sup.2 are identical to or different from each other, R.sup.2 represents a C1-C3 chain hydrocarbon group which may be optionally substituted with one or more halogen atoms, a cyclopropyl group, or a halogen atom, R.sup.3 represents a C1-C6 chain hydrocarbon group which may be optionally substituted with one or more substituents selected from Group A, a C3-C6 cycloalkyl group which may be optionally substituted with one or more substituents selected from Group B, a C6-C10 aryl group, a five- to ten-membered aromatic heterocyclic group {the C6-C10 aryl group, and the five- to ten-membered aromatic heterocyclic group may be optionally substituted with one or more substituents selected from Group C} or a hydrogen atom, R.sup.4 represents a C1-C6 chain hydrocarbon group which may be optionally substituted with one or more substituents selected from Group A, a C3-C6 cycloalkyl group which may be optionally substituted with one or more substituents selected from Group B, a C6-C10 aryl group, or a five- to ten-membered aromatic heterocyclic group {the C6-C10 aryl group, and the five- to ten-membered aromatic heterocyclic group may be optionally substituted with one or more substituents selected from Group C}, R.sup.5 represents a C1-C3 chain hydrocarbon group which may be optionally substituted with one or more halogen atoms, a C1-C3 alkoxy group which may be optionally substituted with one or more halogen atoms, or a hydrogen atom, R.sup.6 represents a C1-C6 chain hydrocarbon group which may be optionally substituted with one or more substituents selected from Group A, a C3-C6 cycloalkyl group which may be optionally substituted with one or more substituents selected from Group B, a C6-C10 aryl group, a five- to ten-membered aromatic heterocyclic group {the C6-C10 aryl group, and the five- to ten-membered aromatic heterocyclic group may be optionally substituted with one or more substituents selected from Group C} or a hydrogen atom, R.sup.3 and R.sup.5 may be combined together with the nitrogen atom to which they are attached to form a four- to seven-membered non-aromatic heterocyclic group {the four- to seven-membered non-aromatic heterocyclic group may have optionally one or more substituents selected from Group B}, Group A: a group consisting of OR.sup.11, S(O).sub.mR.sup.13, OS(O).sub.2R.sup.13, C(O)R.sup.11, C(O)OR.sup.11, OC(O)R.sup.11, OC(O)OR.sup.11, OC(O)NR.sup.11R.sup.12, NR.sup.11C(O)NR.sup.12R.sup.13, NR.sup.11R.sup.12, C(O)NR.sup.11R.sup.12, S(O).sub.2NR.sup.11R.sup.12, NR.sup.12C(O)R.sup.11, NR.sup.12C(O)OR.sup.13, NR.sup.12S(O).sub.2R.sup.13, C(R.sup.12)═N—OR.sup.11, O—N═CR.sup.11R.sup.13, SiR.sup.14R.sup.15R.sup.16, a C3-C6 cycloalkyl group, a phenyl group, a naphthyl group, a five- to six-membered aromatic heterocyclic group, a three- to eight-membered non-aromatic heterocyclic group {the C3-C6 cycloalkyl group, the phenyl group, the naphthyl group, the five- to six-membered aromatic heterocyclic group, and the three- to eight-membered non-aromatic heterocyclic group may be optionally substituted with one or more substituents selected from Group E}, a halogen atom, a cyano group, and a nitro group. R.sup.11 and R.sup.12 are identical to or different from each other, and each represents a C1-C6 chain hydrocarbon group which may be optionally substituted with one or more substituents selected from Group D, a C3-C6 cycloalkyl group which may be optionally substituted with one or more substituents selected from Group E, a phenyl group, a naphthyl group, a five- to six-membered aromatic heterocyclic group, a three- to eight-membered non-aromatic heterocyclic group {the phenyl group, the naphthyl group, the five- to six-membered aromatic heterocyclic group, and the three- to eight-membered non-aromatic heterocyclic group may be optionally substituted with one or more substituents selected from Group F} or a hydrogen atom, R.sup.13 represents a C1-C6 chain hydrocarbon group which may be optionally substituted with one or more substituents selected from Group D, a C3-C6 cycloalkyl group which may be optionally substituted with one or more substituents selected from Group E, a phenyl group, a naphthyl group, a five- to six-membered aromatic heterocyclic group, or a three- to eight-membered non-aromatic heterocyclic group {the phenyl group, the naphthyl group, the five- to six-membered aromatic heterocyclic group, and the three- to eight-membered non-aromatic heterocyclic group may be optionally substituted with one or more substituents selected from Group F}, R.sup.14, R.sup.5 and R.sup.16 are identical to or different from each other, and each represents a C1-C6 chain hydrocarbon group or a phenyl group, m is 0, 1 or 2, Group B: a group consisting of a C1-C6 chain hydrocarbon group which may be optionally substituted with one or more substituents selected from Group D, OR.sup.11, S(O).sub.mR.sup.13, OS(O).sub.2R.sup.13, C(O)R.sup.11, C(O)OR.sup.11, OC(O)R.sup.11, OC(O)OR.sup.11, OC(O)NR.sup.11R.sup.12, NR.sup.11C(O)NR.sup.12R.sup.13, NR.sup.11R.sup.12, C(O)NR.sup.11R.sup.12, S(O).sub.2NR.sup.11R.sup.12, NR.sup.12C(O)R.sup.11, NR.sup.12C(O)OR.sup.13, NR.sup.12S(O).sub.2R.sup.13, C(R.sup.12)═N—OR.sup.11, O—N═CR.sup.11R.sup.13, SiR.sup.14R.sup.15R.sup.16, a C3-C6 cycloalkyl group, a phenyl group, a naphthyl group, a five- to six-membered aromatic heterocyclic group, a three- to eight-membered non-aromatic heterocyclic group {the C3-C6 cycloalkyl group, the phenyl group, the naphthyl group, the five- to six-membered aromatic heterocyclic group, and the three- to eight-membered non-aromatic heterocyclic group may be optionally substituted with one or more substituents selected from Group E}, an oxo group, a thioxo group, a halogen atom, a cyano group, and a nitro group. Group C: a group consisting of a C1-C6 chain hydrocarbon group which may be optionally substituted with one or more substituents selected from Group D, OR.sup.11, S(O).sub.mR.sup.13, OS(O).sub.2R.sup.13, C(O)R.sup.11, C(O)OR.sup.11, OC(O)R.sup.11, OC(O)OR.sup.11, OC(O)NR.sup.11R.sup.12, NR.sup.11C(O)NR.sup.12R.sup.13, NR.sup.11R.sup.12, C(O)NR.sup.11R.sup.12, S(O).sub.2NR.sup.11R.sup.12, NR.sup.12C(O)R.sup.11, NR.sup.12C(O)OR.sup.13, NR.sup.12S(O).sub.2R.sup.13, C(R.sup.12)═N—OR.sup.11, O—N═CR.sup.11R.sup.13, SiR.sup.14R.sup.15R.sup.16, a C3-C6 cycloalkyl group, a phenyl group, a naphthyl group, a five- to six-membered aromatic heterocyclic group, a three- to eight-membered non-aromatic heterocyclic group {the C3-C6 cycloalkyl group, the phenyl group, the naphthyl group, the five- to six-membered aromatic heterocyclic group, and the three- to eight-membered non-aromatic heterocyclic group may be optionally substituted with one or more substituents selected from Group E}, a halogen atom, a cyano group, and a nitro group. Group D: a group consisting of a C3-C6 cycloalkyl group {the C3-C6 cycloalkyl group may be optionally substituted with one or more substituents selected from a group consisting of a halogen atom, a cyano group, and a C1-C3 alkoxy group}, OR.sup.17, S(O).sub.mR.sup.19, OS(O).sub.2R.sup.19, C(O)R.sup.17, C(O)OR.sup.17, OC(O)R.sup.17, OC(O)OR.sup.17, OC(O)NR.sup.17R.sup.18, NR.sup.17C(O).sup.NR.sup.18R.sup.19, NR.sup.17R.sup.18, C(O)NR.sup.17R.sup.18, S(O).sub.2NR.sup.17R.sup.18, NR.sup.18C(O)R.sup.17, NR.sup.18RC(O)OR.sup.19, NR.sup.1BS(O).sub.2R.sup.19, C(R.sup.18)═N—OR.sup.17, O—N═CR.sup.17R.sup.19, SiR.sup.14R.sup.15R.sup.16, a halogen atom, a cyano group, a nitro group, a hydroxy group, a phenoxy group, a phenyl group, a naphthyl group, a five- to six-membered aromatic heterocyclic group and a three- to eight-membered non-aromatic heterocyclic group {the phenoxy group, the phenyl group, the naphthyl group, the five- to six-membered aromatic heterocyclic group, and the three- to eight-membered non-aromatic heterocyclic group may be optionally substituted with one or more substituents selected from Group F}. R.sup.17 and R.sup.18 are identical to or different from each other, and each represents a C1-C6 chain hydrocarbon group, a C3-C6 cycloalkyl group, a phenyl group, a naphthyl group, a five- to six-membered aromatic heterocyclic group, a three- to eight-membered non-aromatic heterocyclic group {the C1-C6 chain hydrocarbon group, the C3-C6 cycloalkyl group, the phenyl group, the naphthyl group, the five- to six-membered aromatic heterocyclic group, and the three- to eight-membered non-aromatic heterocyclic group may be optionally substituted with one or more substituents selected from a group consisting of a halogen atom, a cyano group, and a C1-C3 alkoxy group} or a hydrogen atom, R.sup.19 represents a C1-C6 chain hydrocarbon group, a C3-C6 cycloalkyl group, a phenyl group, a naphthyl group, a five- to six-membered aromatic heterocyclic group, or a three- to eight-membered non-aromatic heterocyclic group {the C1-C6 chain hydrocarbon group, the C3-C6 cycloalkyl group, the phenyl group, the naphthyl group, the five- to six-membered aromatic heterocyclic group, and the three- to eight-membered non-aromatic heterocyclic group may be optionally substituted with one or more substituents selected from a group consisting of a halogen atom, a cyano group, and a C1-C3 alkoxy group}, Group E: a group consisting of a C1-C6 chain hydrocarbon group, a C3-C6 cycloalkyl group {the C1-C6 chain hydrocarbon group, and the C3-C6 cycloalkyl group may be optionally substituted with one or more substituents selected from a group consisting of a halogen atom, a cyano group and a C1-C3 alkoxy group}, OR.sup.17, S(O).sub.mR.sup.19, OS(O).sub.2R.sup.19, C(O)R.sup.17, C(O)OR.sup.17, OC(O)R.sup.17, OC(O)OR.sup.17, OC(O)NR.sup.17R.sup.19, NR.sup.17C(O)NR.sup.18R.sup.19, NR.sup.17R.sup.19, C(O)NR.sup.17R.sup.18, S(O).sub.2NR.sup.17R.sup.1B, NR.sup.18C(O)R.sup.17, NR.sup.18C(O)OR.sup.19, NR.sup.18S(O).sub.2R.sup.19, C(R.sup.18)═N—OR.sup.17, O—N═CR.sup.17R.sup.19, SiR.sup.14R.sup.15R.sup.16, a halogen atom, a cyano group, a nitro group, a hydroxy group, a phenoxy group, a phenyl group, a naphthyl group, a five- to six-membered aromatic heterocyclic group, and a three- to eight-membered non-aromatic heterocyclic group {the phenoxy group, the phenyl group, the naphthyl group, the five- to six-membered aromatic heterocyclic group, and the three- to eight-membered non-aromatic heterocyclic group may be optionally substituted with one or more substituents selected from Group F}. Group F: a group consisting of a C1-C6 chain hydrocarbon group, a C3-C6 cycloalkyl group, a C1-C6 alkoxy group, and a C1-C6 alkylthio group {the C1-C6 chain hydrocarbon group, the C3-C6 cycloalkyl group, the C1-C6 alkoxy group, and the C1-C6 alkylthio group may be optionally substituted with one or more substituents selected from a group consisting of a halogen atom and a cyano group}, a halogen atom, a cyano group, a nitro group, and a hydroxy group.].

2. The compound according to claim 1 wherein E represents a methyl group which is substituted with one or more substituents selected from Group A, or a C2-C10 chain hydrocarbon group which may be optionally substituted with one or more substituents selected from Group A, or its N-oxide compound or agriculturally acceptable salt.

3. The compound according to claim 1 wherein E represents R.sup.6C(O)—, R.sup.4OC(O)—, R.sup.3R.sup.5NC(O)—, R.sup.3R.sup.5NC(S)—, R.sup.4S(O).sub.2—, or R.sup.3R.sup.5NS(O).sub.2—, or its N-oxide compound or agriculturally acceptable salt.

4. The compound according to claim 1 wherein E represents R.sup.3R.sup.5NC(O)—, or its N-oxide compound or agriculturally acceptable salt.

5. The compound according to claim 1 wherein R.sup.1 represents a methyl group or a chlorine atom, n is 0, and L represents an oxygen atom, or its N-oxide compound or agriculturally acceptable salt.

6. A composition for controlling pests, comprising: the compound of claim 1 or its N-oxide compound or agriculturally acceptable salt; and an inert carrier.

7. A composition, comprising: one or more ingredients selected from the group consisting of the following Groups (a), (b), (c) and (d); and the compound of claim 1 or its N-oxide compound or agriculturally acceptable salt: Group (a): a group consisting of insecticidal ingredients, miticidal ingredients, and nematicidal ingredients; Group (b): fungicidal ingredients: Group (c): plant growth modulating ingredients; and Group (d): repellent ingredients.

8. A method for controlling a pest, comprising: applying an effective amount of the compound of claim 1, or its N-oxide or agriculturally acceptable salt to a plant or soil.

9. A method for controlling soybean rust fungus with an amino acid replacement at the F129L position in a mitochondrial cytochrome b protein, comprising: applying an effective amount of the compound of claim 1, or its N-oxide or agriculturally acceptable salt.

10. Use of the compound according to claim 1 or its N-oxide or agriculturally acceptable salt for controlling a pest.

11. A seed or vegetative reproductive organ carrying an effective amount of the compound of claim 1 or its N-oxide or agriculturally acceptable salt.

12. A compound represented by formula (II): ##STR00160## [wherein L represents an oxygen atom or CH.sub.2, R.sup.1 represents a C1-C3 chain hydrocarbon group which may be optionally substituted with one or more halogen atoms, a cyclopropyl group, or a halogen atom, n is 0, 1, 2 or 3, when n is 2 or 3, a plurality of R.sup.2 are identical to or different from each other, R.sup.2 represents a C1-C3 chain hydrocarbon group which may be optionally substituted with one or more halogen atoms, a cyclopropyl group, or a halogen atom.].

13. The compound according to claim 12 wherein R.sup.1 represents a methyl group or a chlorine atom, and n is 0.

14. A compound represented by formula (III): ##STR00161## [wherein L represents an oxygen atom or CH.sub.2, E represents a methyl group which is substituted with one or more substituents selected from Group A, a C2-C10 chain hydrocarbon group which may be optionally substituted with one or more substituents selected from Group A, R.sup.6C(O)—, R.sub.4OC(O)—, R.sup.3R.sup.5NC(O)—, R.sup.3R.sup.5NC(S)—, R.sup.4S(O).sub.2—, or R.sup.3R.sup.5NS(O).sub.2—, R.sup.1 represents a C1-C3 chain hydrocarbon group which may be optionally substituted with one or more halogen atoms, a cyclopropyl group or a halogen atom, n is 0, 1, 2 or 3, when n is 2 or 3, a plurality of R.sup.2 are identical to or different from each other, R.sup.2 represents a C1-C3 chain hydrocarbon group which may be optionally substituted with one or more halogen atoms, a cyclopropyl group, or a halogen atom, R.sup.3 represents a C1-C6 chain hydrocarbon group which may be optionally substituted with one or more substituents selected from Group A, a C3-C6 cycloalkyl group which may be optionally substituted with one or more substituents selected from Group B, a C6-C10 aryl group, a five- to ten-membered aromatic heterocyclic group {the C6-C10 aryl group and the five- to ten-membered aromatic heterocyclic group may be optionally substituted with one or more substituents selected from Group C} or a hydrogen atom, R.sup.4 represents a C1-C6 chain hydrocarbon group which may be optionally substituted with one or more substituents selected from Group A, a C3-C6 cycloalkyl group which may be optionally substituted with one or more substituents selected from Group B, a C6-C10 aryl group, or a five- to ten-membered aromatic heterocyclic group {the C6-C10 aryl group and the five- to ten-membered aromatic heterocyclic group may be optionally substituted with one or more substituents selected from Group C}, R.sup.5 represents a C1-C3 chain hydrocarbon group which may be optionally substituted with one or more halogen atoms, a C1-C3 alkoxy group which may be optionally substituted with one or more halogen atoms, or a hydrogen atom, R.sup.6 represents a C1-C6 chain hydrocarbon group which may be optionally substituted with one or more substituents selected from Group A, a C3-C6 cycloalkyl group which may be optionally substituted with one or more substituents selected from Group B, a C6-C10 aryl group, a five- to ten-membered aromatic heterocyclic group {the C6-C10 aryl group, and the five- to ten-membered aromatic heterocyclic group may be optionally substituted with one or more substituents selected from Group C} or a hydrogen atom, R.sup.3 and R.sup.5 may be combined together with the nitrogen atom to which they are attached to form a four- to seven-membered non-aromatic heterocyclic group {the four- to seven-non-aromatic heterocyclic group may have optionally one or more substituents selected from Group B}. Group A: a group consisting of OR.sup.11, S(O).sub.mR.sup.13, OS(O).sub.2R.sup.13, C(O)R.sup.11, C(O)OR.sup.11, OC(O)R.sup.11, OC(O)OR.sup.11, OC(O)NR.sup.11R.sup.12, NR.sup.11C(O)NR.sup.12R.sup.13, NR.sup.11R.sup.12, C(O)NR.sup.11R.sup.12, S(O).sub.2NR.sup.11R.sup.12, NR.sup.12C(O)R.sup.11, NR.sup.12C(O)OR.sup.13, NR.sup.12S(O).sub.2R.sup.13, C(R.sup.12)═N—OR.sup.11, O—N═CR.sup.11R.sup.13, SiR.sup.14R.sup.15R.sup.16, a C3-C6 cycloalkyl group, a phenyl group, a naphthyl group, a five- to six-membered aromatic heterocyclic group, a three- to eight-membered non-aromatic heterocyclic group {the C3-C6 cycloalkyl group, the phenyl group, the naphthyl group, the five- to six-membered aromatic heterocyclic group and the three- to eight-membered non-aromatic heterocyclic group may be optionally substituted with one or more substituents selected from Group E}, a halogen atom, a cyano group, and a nitro group. R.sup.11 and R.sup.12 are identical to or different from each other, and each represents a C1-C6 chain hydrocarbon group which may be optionally substituted with one or more substituents selected from Group D, a C3-C6 cycloalkyl group which may be optionally substituted with one or more substituents selected from Group E, a phenyl group, a naphthyl group, a five- to six-membered aromatic heterocyclic group, a three- to eight-membered non-aromatic heterocyclic group {the phenyl group, the naphthyl group, the five- to six-membered aromatic heterocyclic group and the three- to eight-membered non-aromatic heterocyclic group may be optionally substituted with one or more substituents selected from Group F} or a hydrogen atom, R.sup.13 represents a C1-C6 chain hydrocarbon group which may be optionally substituted with one or more substituents selected from Group D, a C3-C6 cycloalkyl group which may be optionally substituted with one or more substituents selected from Group E, a phenyl group, a naphthyl group, a five- to six-membered aromatic heterocyclic group, or a three- to eight-membered non-aromatic heterocyclic group {the phenyl group, the naphthyl group, the five- to six-membered aromatic heterocyclic group, and the three- to eight-membered non-aromatic heterocyclic group may be optionally substituted with one or more substituents selected from Group F}, R.sup.14, R.sup.15 and R.sup.16 are identical to or different from each other, and each represents a C1-C6 chain hydrocarbon group, or a phenyl group, m is 0, 1 or 2, Group B: a group consisting of a C1-C6 chain hydrocarbon group which may be optionally substituted with one or more substituents selected from Group D, OR.sup.11, S(O).sub.mR.sup.13, OS(O).sub.2R.sup.13, C(O)R.sup.11, C(O)OR.sup.11, OC(O)R.sup.11, OC(O)OR.sup.11, OC(O)NR.sup.11R.sup.12, NR.sup.11C(O)NR.sup.12R.sup.13, NR.sup.11R.sup.12, C(O)NR.sup.11R.sup.12, S(O).sub.2NR.sup.11R.sup.12, NR.sup.12C(O)R.sup.11, NR.sup.12C(O)OR.sup.13, NR.sup.12S(O).sub.2R.sup.13, C(R.sup.12)═N—OR.sup.11, O—N═CR.sup.11R.sup.13, SiR.sup.14R.sup.15R.sup.16, a C3-C6 cycloalkyl group, a phenyl group, a naphthyl group, a five- to six-membered aromatic heterocyclic group, a three- to eight-membered non-aromatic heterocyclic group {the C3-C6 cycloalkyl group, the phenyl group, the naphthyl group, the five- to six-membered aromatic heterocyclic group, and the three- to eight-membered non-aromatic heterocyclic group may be optionally substituted with one or more substituents selected from Group E}, an oxo group, a thioxo group, a halogen atom, a cyano group, and a nitro group. Group C: a group consisting of a C1-C6 chain hydrocarbon group which may be optionally substituted with one or more substituents selected from Group D, OR.sup.11, S(O).sub.mR.sup.13, OS(O).sub.2R.sup.13, C(O)R.sup.11, C(O)OR.sup.11, OC(O)R.sup.11, OC(O)OR.sup.11, OC(O)NR.sup.11R.sup.12, NR.sup.11C(O)NR.sup.12R.sup.13, NR.sup.11R.sup.12, C(O)NR.sup.11R.sup.12, S(O).sub.2NR.sup.11R.sup.12, NR.sup.12C(O)R.sup.11, NR.sup.12C(O)OR.sup.13, NR.sup.12S(O).sub.2R.sup.13, C(R.sup.12)═N—OR.sup.11, O—N═CR.sup.11R.sup.13, SiR.sup.14R.sup.15R.sup.16, a C3-C6 cycloalkyl group, a phenyl group, a naphthyl group, a five- to six-membered aromatic heterocyclic group, a three- to eight-membered non-aromatic heterocyclic group {the C3-C6 cycloalkyl group, the phenyl group, the naphthyl group, the five- to six-membered aromatic heterocyclic group, and the three- to eight-membered non-aromatic heterocyclic group may be optionally substituted with one or more substituents selected from Group E}, a halogen atom, a cyano group and a nitro group. Group D: a group consisting of C3-C6 cycloalkyl group {the C3-C6 cycloalkyl group may be optionally substituted with one or more substituents selected from a group consisting of a halogen atom, a cyano group and a C1-C3 alkoxy group}, OR.sup.17, S(O).sub.mR.sup.19, OS(O).sub.2R.sup.19, C(O)R.sup.17, C(O)OR.sup.17, OC(O)R.sup.17, OC(O)OR.sup.17, OC(O)NR.sup.17R.sup.18, NR.sup.17C(O)NR.sup.18R.sup.19, NR.sup.17R.sup.19, C(O)NR.sup.17R.sup.19, S(O).sub.2NR.sup.17R.sup.19, NR.sup.19C(O)R.sup.17, NR.sup.18C(O)OR.sup.19, NR.sup.18S(O).sub.2R.sup.19, C(R.sup.18)═N—OR.sup.17, O—N═CR.sup.17R.sup.19, SiR.sup.14R.sup.15R.sup.16, a halogen atom, a cyano group, a nitro group, a hydroxy group, a phenoxy group, a phenyl group, a naphthyl group, a five- to six-membered aromatic heterocyclic group and a three- to eight-membered non-aromatic heterocyclic group {the phenoxy group, the phenyl group, the naphthyl group, the five- to six-membered aromatic heterocyclic group, and the three- to eight-membered non-aromatic heterocyclic group may be optionally substituted with one or more substituents selected from Group F}, R.sup.17 and R.sup.18 are identical to or different from each other, and each represents a C1-C6 chain hydrocarbon group, a C3-C6 cycloalkyl group, a phenyl group, a naphthyl group, a five- to six-membered aromatic heterocyclic group, a three- to eight-membered non-aromatic heterocyclic group {the C1-C6 chain hydrocarbon group, the C3-C6 cycloalkyl group, the phenyl group, the naphthyl group, the five- to six-membered aromatic heterocyclic group, and the three- to eight-membered non-aromatic heterocyclic group may be optionally substituted with one or more substituents selected from a group consisting of a halogen atom, a cyano group and a C1-C3 alkoxy group} or a hydrogen atom, R.sup.19 represents a C1−C6 chain hydrocarbon group, a C3-C6 cycloalkyl group, a phenyl group, a naphthyl group, a five- to six-membered aromatic heterocyclic group, or a three- to eight-membered non-aromatic heterocyclic group {the C1-C6 chain hydrocarbon group, the C3-C6 cycloalkyl group, the phenyl group, the naphthyl group, the five- to six-membered aromatic heterocyclic group, and the three- to eight-membered non-aromatic heterocyclic group may be optionally substituted with one or more substituents selected from a group consisting of a halogen atom, a cyano group and a C1-C3 alkoxy group}, Group E: a group consisting of a C1-C6 chain hydrocarbon group, a C3-C6 cycloalkyl group {the C1-C6 chain hydrocarbon group and the C3-C6 cycloalkyl group may be optionally substituted with one or more substituents selected from a group consisting of a halogen atom, a cyano group and a C1-C3 alkoxy group} OR.sup.17, S(O).sub.mR.sup.19, OS(O).sub.2R.sup.19, C(O)R.sup.17, C(O)OR.sup.17, OC(O)R.sup.17, OC(O)OR.sup.17, OC(O)NR.sup.17R.sup.19, NR.sub.17C(O)NR.sub.18R.sub.19, NR.sub.17R.sub.18, C(O)NR.sub.17R.sub.18, S(O).sub.2NR.sup.17R.sup.18, NR.sup.18C(O)R.sup.17, NR.sup.18C(O)OR.sup.19, NR.sup.18S(O).sub.2R.sup.19, C(R.sup.18)═N—OR.sup.17, O—N═CR.sup.17R.sup.19, SiR.sup.14R.sup.15R.sup.16, a halogen atom, a cyano group, a nitro group, a hydroxy group, a phenoxy group, a phenyl group, a naphthyl group, a five- to six-membered aromatic heterocyclic group and a three- to eight-membered non-aromatic heterocyclic group {the phenoxy group, the phenyl group, the naphthyl group, the five- to six-membered aromatic heterocyclic group, and the three- to eight-membered non-aromatic heterocyclic group may be optionally substituted with one or more substituents selected from Group F}. Group F: a group consisting of a C1-C6 chain hydrocarbon group, a C3-C6 cycloalkyl group, a C1-C6 alkoxy group and a C1-C6 alkylthio group {the C1-C6 chain hydrocarbon group, the C3-C6 cycloalkyl group, the C1-C6 an alkoxy group and the C1-C6 alkylthio group may be optionally substituted with one or more substituents selected from a group consisting of a halogen atom and a cyano group}, a halogen atom, a cyano group, a nitro group and a hydroxy group.].

15. The compound according to claim 14 wherein E represents a methyl group which is substituted with one or more substituents selected from Group A, or a C2-C10 chain hydrocarbon group which may be optionally substituted with one or more substituents selected from Group A.

16. The compound according to claim 14 wherein E represents R.sup.6C(O)—, R.sup.4OC(O)—, R.sup.3R.sup.5NC(O)—, R.sup.3R.sup.5NC(S)—, R4S(O).sub.2—, or R.sup.3R.sup.5NS(O).sub.2—.

17. The compound according to claim 14 wherein E represents R.sup.3R.sup.5NC(O)—.

18. The compound according to claim 14 wherein R.sup.1 represents a methyl group or a chlorine atom, n is 0, and L represents an oxygen atom.

19. A compound represented by formula (IV): ##STR00162## [wherein E represents a methyl group which is substituted with one or more substituents selected from Group A, a C2-C10 chain hydrocarbon group which may be optionally substituted with one or more substituents selected from Group A, R.sup.6C(O)—, R.sup.4OC(O)—, R.sup.3R.sup.5NC(O)—, R.sup.3R.sup.5NC(S)—, R.sup.4S(O).sub.2—, or R.sup.3R.sup.5NS(O).sub.2—, n is 0, 1, 2 or 3, when n is 2 or 3, a plurality of R.sup.2 are identical to or different from each other, R.sup.2 represents a C1-C3 chain hydrocarbon group which may be optionally substituted with one or more halogen atoms, a cyclopropyl group or a halogen atom, R.sup.3 represents a C1-C6 chain hydrocarbon group which may be optionally substituted with one or more substituents selected from Group A, a C3-C6 cycloalkyl group which may be optionally substituted with one or more substituents selected from Group B, a C6-C10 aryl group, a five- to ten-membered aromatic heterocyclic group {the C6-C10 aryl group and the five- to ten-membered aromatic heterocyclic group may be optionally substituted with one or more substituents selected from Group C} or a hydrogen atom, R.sup.4 represents a C1-C6 chain hydrocarbon group which may be optionally substituted with one or more substituents selected from Group A, a C3-C6 cycloalkyl group which may be optionally substituted with one or more substituents selected from Group B, a C6-C10 aryl group, or a five- to ten-membered aromatic heterocyclic group {the C6-C10 aryl group and the five- to ten-membered aromatic heterocyclic group may be optionally substituted with one or more substituents selected from Group C}, R.sup.5 represents a C1-C3 chain hydrocarbon group which may be optionally substituted with one or more halogen atoms, a C1-C3 alkoxy group which may be optionally substituted with one or more halogen atoms, or a hydrogen atom, R.sup.6 represents a C1-C6 chain hydrocarbon group which may be optionally substituted with one or more substituents selected from Group A, a C3-C6 cycloalkyl group which may be optionally substituted with one or more substituents selected from Group B, a C6-C10 aryl group, a five- to ten-membered aromatic heterocyclic group {the C6-C10 aryl group and the five- to ten-membered aromatic heterocyclic group may be optionally substituted with one or more substituents selected from Group C} or a hydrogen atom, R.sup.3 and R.sup.5 may be combined together with the nitrogen atom to which they are attached to form a four- to seven-membered non-aromatic heterocyclic group {the four- to seven-membered non-aromatic heterocyclic group may have optionally one or more substituents selected from Group B}. Group A: a group consisting of OR.sup.11, S(O).sub.mR.sup.13, OS(O).sub.2R.sup.13, C(O)R.sup.11, C(O)OR.sup.11, OC(O)R.sup.11, OC(O)OR.sup.11, OC(O)NR.sup.11R.sup.12, NR.sup.11C(O)NR.sup.12R.sup.13, NR.sup.11R.sup.12, C(O)NR.sup.11R.sup.12, S(O).sub.2NR.sup.11R.sup.12, NR.sup.12C(O)R.sup.11, NR.sup.12C(O)OR.sup.13, NR.sup.12S(O).sub.2R.sup.13, C(R.sup.12)═N—OR.sup.11, O—N═CR.sup.11R.sup.13, SiR.sup.14R.sup.15R.sup.16, a C3-C6 cycloalkyl group, a phenyl group, a naphthyl group, a five- to six-membered aromatic heterocyclic group, a three- to eight-membered non-aromatic heterocyclic group {the C3-C6 cycloalkyl group, the phenyl group, the naphthyl group, the five- to six-membered aromatic heterocyclic group, and the three- to eight-membered non-aromatic heterocyclic group may be optionally substituted with one or more substituents selected from Group E}, a halogen atom, a cyano group, and a nitro group. R.sup.11 and R.sup.12 are identical to or different from each other, and each represents a C1-C6 chain hydrocarbon group which may be optionally substituted with one or more substituents selected from Group E, a C3-C6 cycloalkyl group which may be optionally substituted with one or more substituents selected from Group D, a phenyl group, a naphthyl group, a five- to six-membered aromatic heterocyclic group, a three- to eight-membered non-aromatic heterocyclic group {the phenyl group, the naphthyl group, the five- to six-membered aromatic heterocyclic group, and the three- to eight-membered non-aromatic heterocyclic group may be optionally substituted with one or more substituents selected from Group F} or a hydrogen atom, R.sup.13 represents a C1-C6 chain hydrocarbon group which may be optionally substituted with one or more substituents selected from Group D, a C3-C6 cycloalkyl group which may be optionally substituted with one or more substituents selected from Group E, a phenyl group, a naphthyl group, a five- to six-membered aromatic heterocyclic group or a three- to eight-membered non-aromatic heterocyclic group {the phenyl group, the naphthyl group, the five- to six-membered aromatic heterocyclic group and the three- to eight-membered non-aromatic heterocyclic group may be optionally substituted with one or more substituents selected from Group F}, R.sup.14, R.sup.15 and .sup.R16 are identical to or different from each other, and each represents a C1-C6 chain hydrocarbon group or a phenyl group, m is 0, 1 or 2, Group B: a group consisting of a C1-C6 chain hydrocarbon group which may be optionally substituted with one or more substituents selected from Group D, OR.sup.11, S(O).sub.mR.sup.13, OS(O).sub.2R.sup.13, C(O)R.sup.11, C(O)OR.sup.11, OC(O)R.sup.11, OC(O)OR.sup.11, OC(O)NR.sup.11R.sup.12, NR.sup.11C(O)NR.sup.12R.sup.13, NR.sup.11R.sup.12, C(O)NR.sup.11R.sup.12, S(O).sub.2NR.sup.11R.sup.12, NR.sup.12C(O)R.sup.11, NR.sup.12C(O)OR.sup.11, NR.sup.12S(O).sub.2R.sup.13, C(R.sup.12)═N—OR.sup.11, O—N═CR.sup.11R.sup.13, SiR.sup.14R5R.sup.16, a C3-C6 cycloalkyl group, a phenyl group, a naphthyl group, a five- to six-membered aromatic heterocyclic group, a three- to eight-membered non-aromatic heterocyclic group {the C3-C6 cycloalkyl group, the phenyl group, the naphthyl group, the five- to six-membered aromatic heterocyclic group and the three- to eight-membered non-aromatic heterocyclic group may be optionally substituted with one or more substituents selected from Group E}, an oxo group, a thioxo group, a halogen atom, a cyano group and a nitro group. Group C: a group consisting of a C1-C6 chain hydrocarbon group which may be optionally substituted with one or more substituents selected from Group D, OR.sup.11, S(O).sub.mR.sup.13, OS(O).sub.2R.sup.13, C(O)R.sup.11, C(O)OR.sup.11, OC(O)R.sup.11, OC(O)OR.sup.11, OC(O)NR.sup.11R.sup.12, NR.sup.11C(O)NR.sup.12R.sup.13, NR.sup.11R.sup.12, C(O)NR.sup.11R.sup.12, S(O).sub.2NR.sup.11R.sup.12, NR.sup.12C(O)R.sup.11, NR.sup.12C(O)OR.sup.13, NR.sup.12S(O).sub.2R.sup.13, C(R.sup.12)═N—OR.sup.11, O—N═CR.sup.11R.sup.13, SiR.sup.14R.sup.15R.sup.16, a C3-C6 cycloalkyl group, a phenyl group, a naphthyl group, a five- to six-membered aromatic heterocyclic group, a three- to eight-membered non-aromatic heterocyclic group {the C3-C6 cycloalkyl group, the phenyl group, the naphthyl group, the five- to six-membered aromatic heterocyclic group and the three- to eight-membered non-aromatic heterocyclic group may be optionally substituted with one or more substituents selected from Group E}, a halogen atom, a cyano group and a nitro group. Group D: a group consisting of a C3-C6 cycloalkyl group {the C3-C6 cycloalkyl group may be optionally substituted with one or more substituents selected from a group consisting of a halogen atom, a cyano group and a C1-C3 alkoxy group}, OR.sup.17, S(O).sub.mR.sup.19, OS(O).sub.2R.sup.19, C(O)R.sup.17, C(O)OR.sup.17, OC(O)R.sup.17, OC(O)OR.sup.17, OC(O)NR.sup.17R.sup.18, NR.sup.17C(O)NR.sup.18R.sup.19, NR.sup.17R.sup.19, C(O)NR.sup.17R.sup.18, S(O).sub.2NR.sup.17R.sup.19, NR.sup.19C(O)R.sup.17, NR.sup.18C(O)OR.sup.19, NR.sup.18S(O).sub.2R.sup.19, C(R.sup.18)═N—OR.sup.17, O—N═CR.sup.17R.sup.19, SiR.sup.14R.sup.15R.sup.16, a halogen atom, a cyano group, a nitro group, a hydroxy group, a phenoxy group, a phenyl group, a naphthyl group, a five- to six-membered aromatic heterocyclic group and a three- to eight-membered non-aromatic heterocyclic group {the phenoxy group, the phenyl group, the naphthyl group, the five- to six-membered aromatic heterocyclic group and the three- to eight-membered non-aromatic heterocyclic group may be optionally substituted with one or more substituents selected from Group F}. R.sup.17 and R.sup.18 are identical to or different from each other, and each represents a C1-C6 chain hydrocarbon group, a C3-C6 cycloalkyl group, a phenyl group, a naphthyl group, a five- to six-membered aromatic heterocyclic group, a three- to eight-membered non-aromatic heterocyclic group {the C1-C6 chain hydrocarbon group, the C3-C6 cycloalkyl group, the phenyl group, the naphthyl group, the five- to six-membered aromatic heterocyclic group and the three- to eight-membered non-aromatic heterocyclic group may be optionally substituted with one or more substituents selected from a group consisting of a halogen atom, a cyano group and a C1-C3 alkoxy group} or a hydrogen atom, R.sup.19 represents a C1-C6 chain hydrocarbon group, a C3-C6 cycloalkyl group, a phenyl group, a naphthyl group, a five- to six-membered aromatic heterocyclic group or a three- to eight-membered non-aromatic heterocyclic group {the C1-C6 chain hydrocarbon group, the C3-C6 cycloalkyl group, the phenyl group, the naphthyl group, the five- to six-membered aromatic heterocyclic group and the three- to eight-membered non-aromatic heterocyclic group may be optionally substituted with one or more substituents selected from a group consisting of a halogen atom, a cyano group and a C1-C3 alkoxy group}, Group E: a group consisting of a C1-C6 chain hydrocarbon group, a C3-C6 cycloalkyl group {the C1-C6 chain hydrocarbon group and the C3-C6 cycloalkyl group may be optionally substituted with one or more substituents selected from a group consisting of a halogen atom, a cyano group and a C1-C3 alkoxy group}, OR.sup.17, S(O).sub.mR.sup.19, OS(O).sub.2R.sup.19, C(O)R.sup.17, C(O)OR.sup.17, OC(O)R.sup.17, OC(O)OR.sup.17, OC(O)NR.sup.17R.sup.18, NR.sup.17C(O)NR.sup.18R.sup.19, NR.sup.17R.sup.18, C(O)NR.sup.17R.sup.18, S(O).sub.2NR.sup.17R.sup.18, NR.sup.18C(O)R.sup.17, NR.sup.18C(O)OR.sup.19, NR.sup.18S(O).sub.2R.sup.19, C(R.sup.18)═N—OR.sup.17, O—N═CR.sup.17R.sup.19, SiR.sup.14R.sup.15R.sup.16, a halogen atom, a cyano group, a nitro group, a hydroxy group, a phenoxy group, a phenyl group, a naphthyl group, a five- to six-membered aromatic heterocyclic group and a three- to eight-membered non-aromatic heterocyclic group {the phenoxy group, the phenyl group, the naphthyl group, the five- to six-membered aromatic heterocyclic group and the three- to eight-membered non-aromatic heterocyclic group may be optionally substituted with one or more substituents selected from Group F}. Group F: a group consisting of a C1-C6 chain hydrocarbon group, a C3-C6 cycloalkyl group, a C1-C6 alkoxy group and a C1-C6 alkylthio group {the C1-C6 chain hydrocarbon group, the C3-C6 cycloalkyl group, the C1-C6 alkoxy group and the C1-C6 alkylthio group may be optionally substituted with one or more substituents selected from a group consisting of a halogen atom and a cyano group}, a halogen atom, a cyano group, a nitro group and a hydroxy group.].

20. The compound according to claim 19 wherein n is 0, and E represents a methyl group which is substituted with one or more substituents selected from Group A, or a C2-C10 chain hydrocarbon group which may be optionally substituted with one or more substituents selected from Group A.

21. The compound according to claim 19 wherein n is 0, and E represents R.sup.6C(O)—, R.sup.4OC(O)—, R.sup.3R.sup.5NC(O)—, R.sup.3R.sup.5NC(S)—, R.sup.4S(O).sub.2—, or R.sup.3R.sup.5NS(O).sub.2—.

22. The compound according to claim 19 wherein n is 0, and E represents R.sup.3R.sup.5NC(O)—.

23. A compound represented by formula (VI): ##STR00163## [wherein L represents an oxygen atom or CH.sub.2, R.sup.1 represents a C1-C3 chain hydrocarbon group which may be optionally substituted with one or more halogen atoms, a cyclopropyl group or a halogen atom, R.sup.2 represents a C1-C3 chain hydrocarbon group which may be optionally substituted with one or more halogen atoms, a cyclopropyl group or a halogen atom, n is 0, 1, 2 or 3, when n is 2 or 3, a plurality of R.sup.2 are identical to or different from each other.].

24. The compound according to claim 23 wherein R.sup.1 represents a methyl group or a chlorine atom, and n is 0.

Description

EXAMPLES

[0437] Hereinafter, the present invention is explained in more detail by using Preparation Examples, Reference Preparation Examples, and Formulation Examples, and Test Examples, however, the present invention should not be limited to these examples.

[0438] As used herein, “Me” represents a methyl group, “Et” represents an ethyl group, “Pr” represents a propyl group, “Bu” represents a butyl group, “Pen” represents a pentyl group, “i-Pr” represents an isopropyl group, “i-Bu” represents an isobutyl group, “c-Pr” represents a cyclopropyl group, “c-Bu” represents a cyclobutyl group, “c-Pen” represents a cyclopentyl group, “c-Hex” represents a cyclohexyl group, and “Ph” represents a phenyl group.

[0439] Firstly, a preparation example of the compound of the present invention is shown.

[0440] When the physical property value of a compound is measured by liquid chromatography/mass spectrometry (hereinafter, referred to as LCMS), the measured molecular ion value ([M+H].sup.+ or [M−H].sup.− and relation time (hereinafter, referred to as RT) is described. Each condition of liquid chromatography (hereinafter, referred to as “LC”) and mass spectrometry (hereinafter, referred to as “MS”) is described below.

[Lc Condition]

[0441] Column: L-column2 ODS, inner diameter 4.6 mm, length 30 mm, particle size 3 μm (Chemical Evaluation and Research Institute, Japan)
UV measurement wavelength: 254 nm
Mobile phase: A solution: 0.1% aqueous formic acid,
solution B solution: 0.1% formic acid in acetonitrile,
Flow rate: 2.0 mL/minute
Pump: LC-20AD (manufactured by Shimazu) two machines (high pressure gradient)
Gradient condition: A solution is send under the concentration gradient described in [Table LC1].

TABLE-US-00001 TABLE LC1 Time (min) A solution (%) B solution (%) 0.01 90 10 2.00 0 100 4.00 0 100 4.01 90 10

[Ms Condition]

[0442] Detector: LCMS-2020 (manufactured by Shimazu)
Ionization method: DUIS

Reference Preparation Example 1

[0443] A mixture of methyl (Z)-2-(5-bromo-2-methylphenoxy)-3-methoxyacrylate (prepared according to a method described in WO 2001/000562 A1) 20.0 g, bis(pinacolato)diboron 20.2 g, and [1,1′-bis(diphenylphosphino)ferrocene]palladium (II) dichloride 2.43 g, potassium acetate 19.5 g, and DMSO 250 mL was stirred at 80° C. for 10 hours. Water was added to the resulting mixture, and the resulting mixture was extracted with ethyl acetate. The resulting organic layers were washed with water and saturated brine successively, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The resulting residues were subjected to silica gel column chromatography (ethyl acetate:hexane=1:4) to obtain an intermediate compound 1 represented by the following formula 11.8 g.

##STR00019##

Intermediate compound 1: .sup.1H-NMR (CDCl.sub.3) δ: 7.37 (1H, d), 7.32 (1H, s), 7.16 (1H, d), 7.10 (1H, s), 3.87 (3H, s), 3.69 (3H, s), 2.37 (3H, s), 1.31 (12H, s).

Reference Preparation Example 1-1

[0444] An intermediate compound 2 represented by the following formula was prepared by using methyl (Z)-2-(5-bromo-2-methylbenzyl)-3-methoxyacrylate (which was prepared according to the method described in WO 2001/000562 A1) in the place of methyl (Z)-2-(5-bromo-2-methylphenoxy)-3-methoxyacrylate according to the Reference Preparation Example 1.

##STR00020##

Intermediate compound 2: .sup.1H-NMR (CDCl.sub.3) δ: 7.56-7.51 (2H, m), 7.47 (1H, s), 7.12 (1H, d), 3.85 (3H, s), 3.66 (3H, s), 3.57 (2H, s), 2.36 (3H, s), 1.32 (12H, s).

Reference Preparation Exmaple 1-2

[0445] An intermediate compound 3 represented by the following formula was prepared by using methyl (Z)-2-(5-bromo-2-chlorophenoxy)-3-methoxyacrylate (which was prepared according to the method described in WO 98/03464 A1) in the place of methyl (Z)-2-(5-bromo-2-methylphenoxy)-3-methoxyacrylate according to the Reference Preparation Example 1.

##STR00021##

Intermediate compound 3: .sup.1H-NMR (CDCl.sub.3) δ: 7.38-7.37 (2H, m), 7.36 (1H, s), 7.19-7.17 (1H, m), 3.88 (3H, s), 3.72 (3H, s), 1.32 (12H, s).

Reference Preparation Example 2

[0446] To a mixture of the intermediate compound 1 0.50 g, ethanol 20 mL, acetonitrile 20 mL and water 20 mL was added meta-chloroperoxybenzoic acid (purity 70%, containing 30% water) 0.43 g at room temperature, and the mixture was stirred for 3 hours. To the resulting mixture were added saturated sodium thiosulfate aqueous solution and saturated ammonium chloride aqueous solution successively, and the mixture was stirred for 1 hour. The resulting mixture was concentrated under reduced pressure and extracted with ethyl acetate. The resulting organic layer was washed with water and saturated brine successively, and dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to a silica gel column chromatography to obtain an intermediate compound A1 represented by the following formula 0.29 g.

##STR00022##

Intermediate compound A1: .sup.1H-NMR (CDCl.sub.3) δ: 7.31 (1H, s), 6.98 (1H, d), 6.37 (1H, dd), 6.28 (1H, d), 4.75 (1H, s), 3.86 (3H, s), 3.71 (3H, s), 2.25 (3H, s).

Reference Preparation Example 2-1

[0447] The compound which was prepared according to the Reference Preparation Example 2 and its physical property value are shown below.

##STR00023##

Intermediate compound A2: .sup.1H-NMR (CDCl.sub.3) δ: 7.48 (1H, s), 6.97 (1H, d), 6.61-6.54 (2H, m), 4.67 (1H, br s), 3.84 (3H, s), 3.68 (3H, s), 3.50 (2H, s), 2.27 (3H, s).

##STR00024##

Intermediate compound A3: .sup.1H-NMR (DMSO-D.sub.6) δ: 9.69 (1H, br s), 7.61 (1H, s), 7.19 (1H, d), 6.40 (1H, dd), 6.26 (1H, d), 3.88 (3H, s), 3.66 (3H, s).

Reference Preparation Example 3

[0448] To a mixture of methyl 2-(5-hydroxy-2-methylphenoxy)acetate 0.50 g, triphenylphosphine 0.82 g, benzyl alcohol 0.39 mL and chloroform 10 mL was added bis(2-methoxyethyl) azodicarboxylate 0.78 g at 0° C., and the mixture was stirred at room temperature for 22 hours. To the resulting mixture was added saturated sodium bicarbonate aqueous solution, and the mixture was extracted with ethyl acetate. The resulting organic layer was washed with water and saturated brine successively, and dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to a silica gel column chromatography to obtain an intermediate compound C1 represented by the following formula 0.55 g.

##STR00025##

Intermediate compound C1: .sup.1H-NMR (CDCl.sub.3) δ: 7.45-7.30 (5H, m), 7.05 (1H, d), 6.52 (1H, dd), 6.38 (1H, d), 5.02 (2H, s), 4.62 (2H, s), 3.79 (3H, s), 2.22 (3H, s).

Reference Preparation Example 3-1

[0449] The compound which was prepared according to the Reference Preparation Example 3 and its physical property value are shown below.

[0450] A compound represented by formula (1b1):

##STR00026##

wherein E represents the below-mentioned groups.
Intermediate compound C3 (E: Pr):

[0451] .sup.1H-NMR (CDCl.sub.3) δ: 7.03 (1H, d), 6.43 (1H, dd), 6.31 (1H, d), 4.62 (2H, s), 3.87 (2H, t), 3.80 (3H, s), 2.21 (3H, s), 1.84-1.73 (2H, m), 1.02 (3H, t).

Intermediate compound C4 (E: Bu):

[0452] .sup.1H-NMR (CDCl.sub.3) δ: 7.03 (1H, d), 6.43 (1H, dd), 6.30 (1H, d), 4.62 (2H, s), 3.91 (2H, t), 3.80 (3H, s), 2.21 (3H, s), 1.78-1.70 (2H, m), 1.53-1.42 (2H, m), 0.97 (3H, t).

Intermediate compound C5 (E: i-Bu):

[0453] .sup.1H-NMR (CDCl.sub.3) δ: 7.02 (1H, d), 6.43 (1H, dd), 6.31 (1H, d), 4.63 (2H, s), 3.80 (3H, s), 3.66 (2H, d), 2.21 (3H, s), 2.11-1.99 (1H, m), 1.01 (6H, d).

Intermediate compound C6 (E: Pen):

[0454] .sup.1H-NMR (CDCl.sub.3) δ: 7.03 (1H, d), 6.43 (1H, dd), 6.31 (1H, d), 4.62 (2H, s), 3.90 (2H, t), 3.80 (3H, s), 2.21 (3H, s), 1.82-1.70 (2H, m), 1.46-1.31 (4H, m), 0.93 (3H, t).

Intermediate compound C7 (E: CH.sub.2c-Pr):

[0455] .sup.1H-NMR (CDCl.sub.3) δ: 7.02 (1H, d), 6.41 (1H, dd), 6.34 (1H, d), 4.62 (2H, s), 3.80 (3H, s), 3.74 (2H, d), 2.21 (3H, s), 1.31-1.18 (1H, m), 0.68-0.60 (2H, m), 0.37-0.29 (2H, m).

Intermediate compound C8 (E: CH.sub.2c-Pen):

[0456] .sup.1H-NMR (CDCl.sub.3) δ: 7.02 (1H, d), 6.44 (1H, dd), 6.31 (1H, d), 4.63 (2H, s), 3.80 (3H, s), 3.77 (2H, d), 2.39-2.27 (1H, m), 2.21 (3H, s), 1.88-1.76 (2H, m), 1.67-1.53 (4H, m), 1.40-1.28 (2H, m).

Intermediate compound C9 (E: CH.sub.2c-Hex):

[0457] .sup.1H-NMR (CDCl.sub.3) δ: 7.02 (1H, d), 6.43 (1H, dd), 6.30 (1H, d), 4.62 (2H, s), 3.80 (3H, s), 3.70 (2H, d), 2.20 (3H, s), 1.90-1.80 (2H, m), 1.80-1.66 (4H, m), 1.35-1.14 (3H, m), 1.10-0.97 (2H, m).

Intermediate compound C10 (E: CH.sub.2CH.sub.2Ph):

[0458] .sup.1H-NMR (CDCl.sub.3) δ: 7.36-7.21 (5H, m), 7.03 (1H, d), 6.44 (1H, dd), 6.30 (1H, d), 4.62 (2H, s), 4.13 (2H, t), 3.80 (3H, s), 3.08 (2H, t), 2.21 (3H, s).

Intermediate compound C11 (E: CH.sub.2C≡CH)

[0459] .sup.1H-NMR (CDCl.sub.3) δ: 7.06 (1H, d), 6.52 (1H, dd), 6.38 (1H, d), 4.64 (2H, d), 4.62 (2H, s), 3.80 (3H, s), 2.52 (1H, t), 2.22 (3H, s).

Reference Preparation Example 4

[0460] To a mixture of methyl 2-(5-hydroxy-2-methylphenoxy)acetate 0.30 g, potassium carbonate 0.28 g and DMF 10 mL was added N-methyl-N-phenyl carbamoyl chloride 0.29 g at room temperature, and the mixture was stirred for 3 hours. To the resulting mixture was added saturated ammonium chloride aqueous solution, and the mixture was extracted with ethyl acetate. The resulting organic layer was washed with water and saturated brine successively, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to a silica gel column chromatography to obtain the intermediate compound C2 represented by the following formula 0.47 g.

##STR00027##

Intermediate compound C2: .sup.1H-NMR (CDCl.sub.3) δ: 7.44-7.32 (4H, m), 7.30-7.23 (1H, m), 7.10 (1H, d), 6.72-6.45 (2H, m), 4.62 (2H, s), 3.80 (3H, s), 3.42 (3H, s), 2.25 (3H, s).

Reference Preparation Example 4-1

[0461] The compound which was prepared according to the Reference Preparation Example 4 and its physical property value are shown below.

##STR00028##

Intermediate compound C12: .sup.1H-NMR (CDCl.sub.3) δ: 7.11 (1H, d), 6.66 (1H, dd), 6.50 (1H, d), 4.63 (2H, s), 3.80 (3H, s), 3.08 (3H, s), 3.00 (3H, s), 2.25 (3H, s).

##STR00029##

Intermediate compound C13: .sup.1H-NMR (CDCl.sub.3) δ: 7.10 (1H, d), 6.66 (1H, dd), 6.51 (1H, d), 4.62 (2H, s), 3.80 (3H, s), 3.47-3.32 (4H, m), 2.25 (3H, s), 1.28-1.16 (6H, m).

Reference Preparation Example 5

[0462] To a mixture of the intermediate compound C1 0.24 g, methyl formate 0.15 g, and dimethoxyethane 5 mL was added potassium tert-butoxide 0.21 g under ice-cooling, and the mixture was stirred at room temperature for 1 hour. 1N hydrochloric acid was added to the resulting mixture, and the mixture was extracted with ethyl acetate. The resulting organic layer was dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to obtain the intermediate compound B1 represented by below-mentioned formula 0.19 g.

##STR00030##

Intermediate compound B1: LCMS: 315 [M+H].sup.+, RT=1.90 min.

Reference Preparation Example 5-1

[0463] The compound which was prepared according to the Reference Preparation Example 5 and its physical property value are shown below.

[0464] A compound represented by formula (1d1):

##STR00031##

wherein E represents the following groups.
Intermediate compound B2 (E: Pen): LCMS: 295 [M+H].sup.+, RT=2.05 min.
Intermediate compound B3 (E: CH.sub.2c-Pr): LCMS: 279 [M+H].sup.+, RT=1.82 min.
Intermediate compound B4 (E: CH.sub.2c-Pen): LCMS: 307 [M+H].sup.+, RT=2.07 min.
Intermediate compound B5 (E: CH.sub.2c-Hex): LCMS: 321 [M+H].sup.+, RT=2.16 min.

Reference Preparation Example 6

[0465] To a mixture of 5-bromo-2-methylbenzaldehyde 4.58 g THF 185 mL was added sodium hydride (60%, oily) 1.00 g under ice-cooling, and the mixture was stirred under ice-cooling for 20 minutes. Methyl diethylphosphonoacetate 5.00 g was added to the resulting mixture, and the mixture was stirred at room temperature for 4 hours. To the resulting mixture was added saturated sodium bicarbonate aqueous solution, and the mixture was extracted with ethyl acetate. The resulting organic layer was washed with water and saturated brine successively, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to a silica gel column chromatography to obtain the intermediate compound 4 represented by the following formula 5.80 g.

##STR00032##

Intermediate compound 4: .sup.1H-NMR (CDCl.sub.3) δ: 7.87 (1H, d), 7.66 (1H, d), 7.38 (1H, dd), 7.08 (1H, d), 6.35 (1H, d), 3.82 (3H, s), 2.37 (3H, s).

Reference Preparation Example 7

[0466] A mixture of the intermediate compound 4 108.43 g, cobalt(II) chloride 5.52 g, and methanol 1084 mL was cooled to −54° C., and thereto was added sodium borohydride 40.35 g, and the mixture was stirred at −24° C. for 6 hours. To the resulting mixture was added 10% aqueous ammonium chloride solution, and the mixture was extracted with ethyl acetate. The resulting organic layer was washed with water, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to obtain the intermediate compound 5 represented by the below-mentioned formula 93.91 g.

##STR00033##

Intermediate compound 5: .sup.1H-NMR (CDCl.sub.3) δ: 7.27-7.22 (2H, m), 7.01 (1H, d), 3.69 (3H, s), 2.90 (2H, t), 2.58 (2H, t), 2.26 (3H, s).

Reference Preparation Example 8

[0467] A mixture of the intermediate compound 5 3.80 g and THF 137 mL was cooled to −72° C., and thereto was added lithium diisopropylamide (1.08 M hexane-THF solution) 27 mL, and the mixture was stirred at −66° C. for 30 minutes. To the resulting mixture was added methyl formate 7.10 g, and the mixture was stirred at −63° C. for 1 hour. To the resulting mixture was added 10% aqueous sodium hydrogen sulfate solution, and the mixture was extracted with ethyl acetate. The resulting organic layer was washed with water, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to obtain the crude methyl 2-(5-bromo-2-methylbenzyl)-3-hydroxyacrylate. To the obtained crude methyl 2-(5-bromo-2-methylbenzyl)-3-hydroxyacrylate was added DMF 137 mL, and thereto were added potassium carbonate 6.13 g and dimethyl sulfate 4.66 g successively, and the mixture was stirred at room temperature for 4 hours. Water was added to the resulting mixture, and the mixture was extracted with MTBE. The resulting organic layer was washed with water, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to obtain the intermediate compound E1 represented by the below-mentioned formula 3.61 g.

##STR00034##

Intermediate Compound E1

Reference Preparation Example 8-1

[0468] The compound which was prepared according to the Reference Preparation Example 8 and its physical property value are shown below.

[0469] A compound represented by formula (II-A):

##STR00035##

wherein n is 0, and a combination of R.sup.1, X.sup.2 and L represents any combinations indicated in [Table II-A].

TABLE-US-00002 TABLE II-A Intermediate compound R.sup.1 R.sup.2 R.sup.3 E1 Me Br CH.sub.2 E2 Me Br O E3 Cl Br CH.sub.2 E4 Cl Br O
Intermediate compound E1: .sup.1H-NMR (CDCl.sub.3) δ: 7.49 (1H, s), 7.20 (2H, m), 6.97 (1H, d), 3.86 (3H, s), 2.68 (3H, s), 3.50 (2H, m), 2.28 (3H, s).

Reference Preparation Example 9

[0470] To a mixture of 5-chloro-2-methylphenol 2.00 g, potassium carbonate 2.33 g, and DMF 20 mL was added methyl 2-bromoacetate 2.58 g, and the mixture was stirred at room temperature for 3 hours. Water was added to the resulting mixture, and the mixture was extracted with ethyl acetate. The resulting organic layer was washed with water and saturated brine successively, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to a silica gel column chromatography (ethyl acetate:hexane=1:4) to obtain the intermediate compound 6 represented by the following formula 2.94 g.

##STR00036##

Intermediate compound 6: .sup.1H-NMR (CDCl.sub.3) δ: 7.07 (1H, dd), 6.89 (1H, dd), 6.68 (1H, d), 4.64 (2H, s), 3.81 (3H, s), 2.24 (3H, s).

Reference Preparation Example 10

[0471] To a mixture of the intermediate compound 6 3.00 g, methyl formate 2.3 mL and 1,2-dimethoxyethane 20 mL was added potassium tert-butoxide 3.15 g under ice-cooling. The mixture was stirred at room temperature for 2 hours. To the resulting mixture was 1N hydrochloric acid, and the mixture was extracted with ethyl acetate. The resulting organic layer was washed with water, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to obtain the intermediate compound 7 represented by the following formula 2.44 g.

##STR00037##

Intermediate compound 7: .sup.1H-NMR (CDCl.sub.3) δ: 7.53 (1H, d), 7.11 (1H, dt), 6.94 (1H, dd), 6.73 (1H, d), 5.76 (1H, d), 3.71 (3H, t), 2.32 (3H, s).

Reference Preparation Example 11

[0472] To a mixture of the intermediate 7 1.09 g, potassium carbonate 0.70 g, and DMF 10 mL was added iodomethane 0.62 mL under ice-cooling, and the mixture was stirred at room temperature for 2 hours. Water was added to the resulting mixture, and the mixture was extracted with MTBE. The resulting organic layer was washed with water and saturated brine successively, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to a silica gel column chromatography (ethyl acetate; hexane=1:4) to obtain the intermediate compound D2 represented by the following formula 1.00 g.

##STR00038##

Intermediate Compound D2

Reference Preparation Example 11-1

[0473] The compound which was prepared according to the Reference Preparation Example 11 and its physical property value are shown below.

[0474] A compound represented by formula (VI):

##STR00039##

wherein n is 0, and a combination of R.sup.1 and L represents any combinations indicated in [Table VI].

TABLE-US-00003 TABLE VI Intermediate compound R.sup.1 L Intermediate Me CH.sub.2 compound D1 Intermediate Me O compound D2 Intermediate Cl CH.sub.2 compound D3 Intermediate Cl O compound D4
Intermediate compound D1: .sup.1H-NMR (CDCl.sub.3) δ: 7.49 (1H, s), 7.06-7.01 (3H, m), 3.86 (3H, s), 3.68 (3H, s), 3.50 (2H, s), 2.31 (3H, s).
Intermediate compound D2: .sup.1H-NMR (CDCl.sub.3) δ: 7.33 (1H, s), 7.07 (1H, dd), 6.88 (1H, dd), 6.70 (1H, d), 3.89 (3H, s), 3.72 (3H, s), 2.30 (3H, s).

Preparation Example 1

[0475] To a mixture of the intermediate compound A1 0.25 g, triphenylphosphine 0.33 g, ethanol 0.06 mL and chloroform 5 mL was added bis(2-methoxyethyl) azodicarboxylate 0.32 g at 0° C., and the mixture was stirred at room temperature for 16 hours. To the resulting mixture was added saturated sodium bicarbonate aqueous solution, and the mixture was extracted with ethyl acetate. The resulting organic layer was washed with water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to a silica gel column chromatography (ethyl acetate:hexane=1:4) to obtain the present compound 1 represented by the following formula 0.23 g.

##STR00040##

Present compound 1: .sup.1H-NMR (CDCl.sub.3) δ: 7.30 (1H, s), 7.03 (1H, d), 6.44 (1H, dd), 6.33 (1H, d), 3.95 (2H, q), 3.86 (3H, s), 3.70 (3H, s), 2.27 (3H, s), 1.37 (3H, t).

Preparation Example 1-1

[0476] The compound which was prepared according to the Preparation Example 1 and its physical property value are shown below.

[0477] A compound represented by formula (1a1):

##STR00041##

wherein a combination of E, R.sup.1 and L represents any combinations indicated in [Table 1-1] to [Table 1-6].

TABLE-US-00004 TABLE 1-1 Present compound E R.sup.1 L 2 [00042] Me O 3 [00043] Me O 4 [00044] Me O 5 [00045] Me O 6 [00046] Me O 7 [00047] Me O 8 [00048] Me O 9 [00049] Me O 10 [00050] Me O

TABLE-US-00005 TABLE 1-2 Present compound E R.sup.1 L 11 [00051] Me O 12 [00052] Me O 13 [00053] Me O 14 [00054] Me O 15 [00055] Me O 16 [00056] Me O 17 [00057] Me O 18 [00058] Me O 19 [00059] Me O 20 [00060] Me O

TABLE-US-00006 Table 1-3 Present compound E R.sup.1 L 21 [00061] Me O 22 [00062] Me O 23 [00063] Me O 24 [00064] Me O 25 [00065] Me O 26 [00066] Me O 27 [00067] Me O 28 [00068] Me CH.sub.2 29 [00069] Me O 30 [00070] Me O

TABLE-US-00007 TABLE 1-4 Present compound E R.sup.1 L 31 [00071] Me O 32 [00072] Me O 33 [00073] Me O 34 [00074] Me O 35 [00075] Me O 36 [00076] Me O 37 [00077] Me O 38 [00078] Me O 39 [00079] Me O

TABLE-US-00008 TABLE 1-5 Present compound E R.sup.1 L 71 [00080] Me CH.sub.2 72 [00081] Cl O 73 [00082] Me CH.sub.2 74 [00083] Me CH.sub.2 75 [00084] Me O 76 [00085] Me CH.sub.2 77 [00086] Cl O 78 [00087] Me CH.sub.2 79 [00088] Cl O 80 [00089] Me O

TABLE-US-00009 TABLE 1-6 Present compound E R.sup.1 L 81 [00090] Me CH.sub.2 82 [00091] Me CH.sub.2 83 [00092] Me CH.sub.2 84 [00093] Me CH.sub.2 85 [00094] Me CH.sub.2 86 [00095] Me O 87 [00096] Me O 88 [00097] Me O
Present compound 2: .sup.1H-NMR (CDCl.sub.3) δ: 7.30 (1H, s), 7.02 (1H, d), 6.45 (1H, dd), 6.31 (1H, d), 4.50-4.40 (1H, m), 3.86 (3H, s), 3.70 (3H, s), 2.27 (3H, s), 1.29 (6H, d).
Present compound 3: .sup.1H-NMR (CDCl.sub.3) δ: 7.31 (1H, s), 7.03 (1H, d), 6.45 (1H, dd), 6.33 (1H, d), 3.86 (3H, s), 3.84 (2H, t), 3.70 (3H, s), 2.27 (3H, s), 1.82-1.71 (2H, m), 1.01 (3H, t).
Present compound 4: .sup.1H-NMR (CDCl.sub.3) δ: 7.31 (1H, s), 7.03 (1H, d), 6.44 (1H, dd), 6.32 (1H, d), 3.87 (3H, s), 3.71 (3H, s), 3.63 (2H, d), 2.27 (3H, s), 2.09-1.97 (1H, m), 1.00 (6H, d).
Present compound 5: .sup.1H-NMR (CDCl.sub.3) δ: 7.33 (1H, s), 7.02 (1H, d), 6.44 (1H, dd), 6.31 (1H, d), 3.88 (3H, s), 3.71 (3H, s), 3.50 (2H, s), 2.26 (3H, s), 1.00 (9H, s).
Present compound 6: .sup.1H-NMR (CDCl.sub.3) δ: 7.30 (1H, s), 7.03 (1H, d), 6.44 (1H, dd), 6.32 (1H, d), 3.88 (2H, t), 3.86 (3H, s), 3.70 (3H, s), 2.27 (3H, s), 1.76-1.67 (2H, m), 1.52-1.40 (2H, m), 0.96 (3H, t).
Present compound 7: .sup.1H-NMR (CDCl.sub.3) δ: 7.30 (1H, s), 7.02 (1H, d), 6.44 (1H, dd), 6.31 (1H, d), 4.30-4.22 (1H, m), 3.86 (3H, s), 3.70 (3H, s), 2.26 (3H, s), 1.74-1.62 (1H, m), 1.53-1.33 (3H, m), 1.24 (3H, d), 0.92 (3H, t).
Present compound 8: .sup.1H-NMR (CDCl.sub.3) δ: 7.31 (1H, s), 7.02 (1H, d), 6.44 (1H, dd), 6.32 (1H, d), 3.86 (3H, s), 3.76-3.62 (2H, m), 3.70 (3H, s), 2.26 (3H, s), 1.86-1.76 (1H, m), 1.59-1.48 (1H, m), 1.29-1.17 (1H, m), 0.98 (3H, d), 0.93 (3H, t).
Present compound 9: .sup.1H-NMR (CDCl.sub.3) δ: 7.31 (1H, s), 7.03 (1H, d), 6.45 (1H, dd), 6.32 (1H, d), 3.90 (2H, t), 3.86 (3H, s), 3.70 (3H, s), 2.27 (3H, s), 1.84-1.75 (1H, m), 1.63 (2H, q), 0.94 (6H, d).
Present compound 10: .sup.1H-NMR (CDCl.sub.3) δ: 7.32 (1H, s), 7.03 (1H, d), 6.46 (1H, dd), 6.32 (1H, d), 3.87 (3H, s), 3.77 (2H, d), 3.71 (3H, s), 2.27 (3H, s), 1.66-1.58 (1H, m), 1.52-1.36 (4H, m), 0.91 (6H, t).
Present compound 11: .sup.1H-NMR (CDCl.sub.3) δ: 7.30 (1H, s), 7.03 (1H, d), 6.44 (1H, dd), 6.32 (1H, d), 3.87 (2H, t), 3.86 (3H, s), 3.70 (3H, s), 2.26 (3H, s), 1.78-1.69 (2H, m), 1.46-1.31 (4H, m), 0.92 (3H, t).
Present compound 12: .sup.1H-NMR (CDCl.sub.3) δ: 7.30 (1H, s), 7.03 (1H, d), 6.43 (1H, dd), 6.37 (1H, d), 3.86 (3H, s), 3.72 (2H, d), 3.70 (3H, s), 2.27 (3H, s), 1.29-1.19 (1H, m), 0.63 (2H, q), 0.32 (2H, q).
Present compound 13: .sup.1H-NMR (CDCl.sub.3) δ: 7.31 (1H, s), 7.02 (1H, d), 6.44 (1H, dd), 6.32 (1H, d), 3.86 (3H, s), 3.74 (2H, d), 3.70 (3H, s), 2.36-2.26 (1H, m), 2.26 (3H, s), 1.87-1.75 (2H, m), 1.66-1.53 (4H, m), 1.38-1.27 (2H, m).
Present compound 14: .sup.1H-NMR (CDCl.sub.3) δ: 7.31 (1H, s), 7.02 (1H, d), 6.43 (1H, dd), 6.31 (1H, d), 3.86 (3H, s), 3.70 (3H, s), 3.66 (2H, d), 2.26 (3H, s), 1.89-1.64 (6H, m), 1.34-1.15 (3H, m), 1.07-0.94 (2H, m).
Present compound 15: .sup.1H-NMR (CDCl.sub.3) δ: 7.31 (1H, s), 7.03 (1H, d), 6.46 (1H, dd), 6.33 (1H, d), 3.95 (2H, t), 3.86 (3H, s), 3.70 (3H, s), 2.27 (3H, s), 1.63 (2H, q), 0.87-0.76 (1H, m), 0.50-0.43 (2H, m), 0.12-0.06 (2H, m).
Present compound 16: .sup.1H-NMR (CDCl.sub.3) δ: 7.32 (1H, s), 7.04 (1H, d), 6.46 (1H, dd), 6.33 (1H, d), 4.69 (1H, t), 4.57 (1H, t), 4.02 (2H, t), 3.87 (3H, s), 3.71 (3H, s), 2.28 (3H, s), 2.20-2.06 (2H, m).
Present compound 17: .sup.1H-NMR (CDCl.sub.3) δ: 7.32 (1H, s), 7.05 (1H, d), 6.44 (1H, dd), 6.32 (1H, d), 4.12 (2H, t), 3.87 (3H, s), 3.71 (3H, s), 2.63-2.51 (2H, m), 2.27 (3H, s).
Present compound 18: .sup.1H-NMR (CDCl.sub.3) δ: 7.32 (1H, s), 7.04 (1H, d), 6.43 (1H, dd), 6.31 (1H, d), 3.93 (2H, t), 3.87 (3H, s), 3.71 (3H, s), 2.33-2.22 (2H, m), 2.27 (3H, s), 2.04-1.96 (2H, m).
Present compound 19: .sup.1H-NMR (CDCl.sub.3) δ: 7.31 (1H, s), 7.05 (1H, d), 6.45 (1H, dd), 6.36 (1H, d), 4.16 (2H, t), 3.87 (3H, s), 3.77 (2H, t), 3.71 (3H, s), 2.28 (3H, s).
Present compound 20: .sup.1H-NMR (CDCl.sub.3) δ: 7.31 (1H, s), 7.04 (1H, d), 6.46 (1H, dd), 6.32 (1H, d), 4.03 (2H, t), 3.87 (3H, s), 3.72 (2H, t), 3.71 (3H, s), 2.27 (3H, s), 2.23-2.15 (2H, m).
Present compound 21: .sup.1H-NMR (CDCl.sub.3) δ: 7.29 (1H, s), 7.03 (1H, d), 6.46 (1H, dd), 6.40 (1H, d), 4.04 (2H, t), 3.86 (3H, s), 3.71 (2H, t), 3.69 (3H, s), 3.44 (3H, s), 2.27 (3H, s).
Present compound 22: .sup.1H-NMR (CDCl.sub.3) δ: 7.31 (1H, s), 7.04 (1H, d), 6.45 (1H, dd), 6.38 (1H, d), 4.14 (1H, dd), 3.91-3.85 (1H, m), 3.87 (3H, s), 3.71 (3H, s), 3.34-3.29 (1H, m), 2.91-2.87 (1H, m), 2.74 (1H, dd), 2.27 (3H, s).
Present compound 23: .sup.1H-NMR (CDCl.sub.3) δ: 7.30 (1H, s), 7.02 (1H, d), 6.45 (1H, dd), 6.38 (1H, d), 4.27-4.19 (1H, m), 3.96-3.78 (4H, m), 3.86 (3H, s), 3.70 (3H, s), 2.26 (3H, s), 2.10-1.88 (3H, m), 1.77-1.67 (1H, m).
Present compound 24: .sup.1H-NMR (CDCl.sub.3) δ: 7.30 (1H, s), 7.03 (1H, d), 6.45 (1H, dd), 6.35 (1H, d), 4.02 (2H, t), 3.86 (3H, s), 3.70 (3H, s), 2.72 (2H, t), 2.53-2.43 (4H, m), 2.26 (3H, s), 1.64-1.56 (4H, m), 1.48-1.40 (2H, m).
Present compound 25: .sup.1H-NMR (CDCl.sub.3) δ: 7.30 (1H, s), 7.03 (1H, d), 6.43 (1H, dd), 6.31 (1H, d), 3.99 (2H, t), 3.86 (3H, s), 3.70 (3H, s), 2.27 (3H, s), 1.09 (2H, t), 0.06 (9H, s).
Present compound 26: .sup.1H-NMR (CDCl.sub.3) δ: 7.30 (1H, s), 7.03 (1H, d), 6.44 (1H, dd), 6.33 (1H, d), 3.86 (3H, s), 3.83 (2H, t), 3.70 (3H, s), 2.27 (3H, s), 1.79-1.69 (2H, m), 0.60-0.54 (2H, m), 0.01 (9H, s).
Present compound 27: .sup.1H-NMR (CDCl.sub.3) δ: 7.31 (1H, s), 7.05 (1H, d), 6.44-6.38 (2H, m), 4.56 (2H, s), 3.87 (3H, s), 3.80 (3H, s), 3.71 (3H, s), 2.28 (3H, s).
Present compound 28: .sup.1H-NMR (CDCl.sub.3) δ: 7.46 (1H, s), 7.44-7.28 (5H, m), 7.02 (1H, d), 6.75 (1H, d), 6.69 (1H, dd), 4.99 (2H, s), 3.81 (3H, s), 3.66 (3H, s), 3.51 (2H, s), 2.28 (3H, s).
Present compound 29: .sup.1H-NMR (CDCl.sub.3) δ: 7.35-7.21 (6H, m), 7.03 (1H, d), 6.45 (1H, dd), 6.32 (1H, d), 4.09 (2H, t), 3.85 (3H, s), 3.70 (3H, s), 3.06 (2H, t), 2.27 (3H, s).
Present compound 30: .sup.1H-NMR (CDCl.sub.3) δ: 7.40-7.34 (2H, m), 7.29 (1H, s), 7.09-7.01 (3H, m), 6.51 (1H, dd), 6.38 (1H, d), 4.93 (2H, s), 3.84 (3H, s), 3.69 (3H, s), 2.27 (3H, s).
Present compound 31: .sup.1H-NMR (CDCl.sub.3) δ: 7.39-7.30 (4H, m), 7.29 (1H, s), 7.14-6.98 (6H, m), 6.54 (1H, dd), 6.41 (1H, d), 4.94 (2H, s), 3.85 (3H, s), 3.69 (3H, s), 2.28 (3H, s).
Present compound 32: .sup.1H-NMR (CDCl.sub.3) δ: 7.66 (1H, t), 7.45 (1H, d), 7.31 (1H, s), 7.25 (1H, d), 7.04 (1H, d), 6.50 (1H, dd), 6.40 (1H, d), 5.09 (2H, s), 3.86 (3H, s), 3.70 (3H, s), 2.27 (3H, s).
Present compound 33: .sup.1H-NMR (CDCl.sub.3) δ: 8.76 (1H, s), 7.94 (1H, d), 7.70 (1H, d), 7.31 (1H, s), 7.07 (1H, d), 6.51 (1H, dd), 6.38 (1H, d), 5.08 (2H, s), 3.86 (3H, s), 3.70 (3H, s), 2.28 (3H, s).
Present compound 34: .sup.1H-NMR (CDCl.sub.3) δ: 7.33-7.29 (2H, m), 7.10-6.98 (3H, m), 6.54 (1H, dd), 6.41 (1H, d), 5.13 (2H, s), 3.85 (3H, s), 3.69 (3H, s), 2.28 (3H, s).
Present compound 35: .sup.1H-NMR (CDCl.sub.3) δ: 7.78 (1H, d), 7.35 (1H, d), 7.31 (1H, s), 7.06 (1H, d), 6.55 (1H, dd), 6.44 (1H, d), 5.30 (2H, s), 3.86 (3H, s), 3.70 (3H, s), 2.28 (3H, s).
Present compound 36: .sup.1H-NMR (CDCl.sub.3) δ: 7.32 (1H, s), 7.07 (1H, d), 6.72 (1H, s), 6.49 (1H, dd), 6.38 (1H, d), 5.12 (2H, s), 4.44 (2H, q), 3.87 (3H, s), 3.71 (3H, s), 2.28 (3H, s), 1.41 (3H, t).
Present compound 37: .sup.1H-NMR (CDCl.sub.3) δ: 7.32 (1H, s), 7.05 (1H, d), 6.46 (1H, dd), 6.37 (1H, d), 5.54-5.52 (1H, m), 5.42-5.40 (1H, m), 4.50 (2H, t), 3.87 (3H, s), 3.71 (3H, s), 2.27 (3H, s).
Present compound 38: .sup.1H-NMR (CDCl.sub.3) δ: 7.32 (1H, s), 7.05 (1H, d), 6.43 (1H, dd), 6.32 (1H, d), 6.11 (1H, t), 4.59 (2H, d), 3.87 (3H, s), 3.71 (3H, s), 2.28 (3H, s).
Present compound 39: .sup.1H-NMR (CDCl.sub.3) δ: 7.38-7.28 (6H, m), 7.01 (1H, d), 6.46 (1H, dd), 6.36 (1H, d), 5.12 (2H, s), 4.45 (2H, s), 3.85 (3H, s), 3.70 (3H, s), 2.27 (3H, s), 1.97 (3H, s).
Present compound 71: .sup.1H-NMR (CDCl.sub.3) δ: 7.47 (1H, s), 7.00 (1H, d), 6.67 (1H, d), 6.61 (1H, dd), 3.85 (2H, t), 3.83 (3H, s), 3.66 (3H, s), 3.51 (2H, s), 2.27 (3H, s), 1.82-1.71 (2H, m), 1.01 (3H, t).
Present compound 72: .sup.1H-NMR (CDCl.sub.3) δ: 7.33 (1H, s), 7.24 (1H, d), 6.48 (1H, dd), 6.39 (1H, d), 3.90-3.85 (5H, m), 3.72 (3H, s), 1.77-1.68 (2H, m), 1.52-1.41 (2H, m), 0.96 (3H, t).
Present compound 73: .sup.1H-NMR (CDCl.sub.3) δ: 7.48 (1H, s), 7.00 (1H, d), 6.67 (1H, d), 6.61 (1H, dd), 3.83 (3H, s), 3.67 (3H, s), 3.65 (2H, d), 3.51 (2H, s), 2.27 (3H, s), 2.09-1.98 (1H, m), 0.99 (6H, d).
Present compound 74: .sup.1H-NMR (CDCl.sub.3) δ: 7.47 (1H, s), 7.00 (1H, d), 6.69-6.58 (2H, m), 3.88 (2H, t), 3.83 (3H, s), 3.67 (3H, s), 3.51 (2H, s), 2.27 (3H, s), 1.78-1.71 (2H, m), 1.47-1.30 (4H, m), 0.92 (3H, t).
Present compound 75: .sup.1H-NMR (CDCl.sub.3) δ: 7.30 (1H, s), 7.02 (1H, d), 6.44 (1H, dd), 6.32 (1H, d), 3.87 (2H, t), 3.86 (3H, s), 3.70 (3H, s), 2.26 (3H, s), 1.77-1.69 (2H, m), 1.46-1.24 (12H, m), 0.88 (3H, t).
Present compound 76: .sup.1H-NMR (CDCl.sub.3) δ: 7.47 (1H, s), 7.00 (1H, d), 6.68 (1H, d), 6.60 (1H, dd), 3.83 (3H, s), 3.72 (2H, d), 3.66 (3H, s), 3.50 (2H, s), 2.26 (3H, s), 1.28-1.19 (1H, m), 0.64-0.58 (2H, m), 0.34-0.29 (2H, m).
Present compound 77: .sup.1H-NMR (CDCl.sub.3) δ: 7.42-7.24 (7H, m), 6.57 (1H, dd), 6.48 (1H, d), 4.98 (2H, s), 3.84 (3H, s), 3.70 (3H, s).
Present compound 78: .sup.1H-NMR (CDCl.sub.3) δ: 7.47 (1H, s), 7.34-7.19 (5H, m), 7.00 (1H, d), 6.69 (1H, d), 6.62 (1H, dd), 4.11 (2H, t), 3.81 (3H, s), 3.66 (3H, s), 3.51 (2H, s), 3.06 (2H, t), 2.27 (3H, s).
Present compound 79: .sup.1H-NMR (CDCl.sub.3) δ: 7.36-7.21 (7H, m), 6.48 (1H, dd), 6.39 (1H, d), 4.09 (2H, t), 3.86 (3H, s), 3.71 (3H, s), 3.06 (2H, t).
Present compound 80: .sup.1H-NMR (CDCl.sub.3) δ: 7.30 (1H, s), 7.29-7.25 (2H, m), 7.21-7.15 (3H, m), 7.02 (1H, d), 6.43 (1H, dd), 6.31 (1H, d), 3.91-3.87 (2H, m), 3.85 (3H, s), 3.69 (3H, s), 2.70-2.63 (2H, m), 2.26 (3H, s), 1.80-1.75 (4H, m)).
Present compound 81: .sup.1H-NMR (CDCl.sub.3) δ: 7.48 (1H, s), 7.01 (1H, d), 6.70 (1H, d), 6.63 (1H, dd), 6.10-5.98 (1H, m), 5.42-5.34 (1H, m), 5.28-5.23 (1H, m), 4.49-4.45 (2H, m), 3.83 (3H, s), 3.67 (3H, s), 3.51 (2H, s), 2.28 (3H, s).
Present compound 82: .sup.1H-NMR (CDCl.sub.3) δ: 7.48 (1H, s), 7.03 (1H, d), 6.75 (1H, d), 6.69 (1H, dd), 4.62 (2H, d), 3.83 (3H, s), 3.67 (3H, s), 3.51 (2H, s), 2.49 (1H, t), 2.29 (3H, s).
Present compound 83: .sup.1H-NMR (CDCl.sub.3) δ: 7.46 (1H, s), 7.34 (2H, d), 7.02 (1H, d), 6.90 (2H, d), 6.74 (1H, d), 6.69 (1H, dd), 4.91 (2H, s), 3.82 (3H, s), 3.81 (3H, s), 3.66 (3H, s), 3.51 (2H, s), 2.28 (3H, s).
Present compound 84: .sup.1H-NMR (CDCl.sub.3) δ: 7.46 (1H, s), 7.36-7.28 (1H, m), 7.20-7.12 (2H, m), 7.04-6.95 (2H, m), 6.73 (1H, d), 6.67 (1H, dd), 4.99 (2H, s), 3.82 (3H, s), 3.66 (3H, s), 3.51 (2H, s), 2.28 (3H, s).
Present compound 85: .sup.1H-NMR (CDCl.sub.3) δ: 7.47 (1H, s), 7.31-7.27 (1H, m), 7.10-6.96 (3H, m), 6.75 (1H, d), 6.70 (1H, dd), 5.14 (2H, s), 3.81 (3H, s), 3.66 (3H, s), 3.51 (2H, s), 2.28 (3H, s).
Present compound 86: .sup.1H-NMR (CDCl.sub.3) δ: 7.49-7.46 (1H, m), 7.42-7.40 (1H, m), 7.29 (1H, s), 7.05 (1H, d), 6.52 (1H, dd), 6.47-6.45 (1H, m), 6.39 (1H, d), 4.85 (2H, s), 3.85 (3H, s), 3.69 (3H, s), 2.28 (3H, s).
Present compound 87: .sup.1H-NMR (CDCl.sub.3) δ: 8.58-8.55 (2H, m), 7.32 (1H, s), 7.07 (1H, d), 6.52 (1H, dd), 6.42 (1H, d), 5.14 (2H, s), 3.87 (3H, s), 3.71 (3H, s), 2.28 (3H, s).
Present compound 88: .sup.1H-NMR (CDCl.sub.3) δ: 7.31 (1H, s), 7.02 (1H, d), 6.52-6.46 (1H, m), 6.36-6.27 (1H, m), 4.17-3.98 (2H, m), 3.87 (3H, s), 3.85-3.65 (1H, m), 3.71 (3H, s), 3.43-3.27 (2H, m), 2.26 (3H, s), 2.06-1.77 (4H, m), 1.47 (9H, s).

Preparation Example 2

[0478] To a mixture of the intermediate compound A1 0.29 g, potassium carbonate 0.25 g, and DMF 10 mL was added benzyl bromide 0.16 mL at room temperature, and the mixture was stirred for 3 hours. Water was added to the resulting mixture, and the mixture was extracted with ethyl acetate. The resulting organic layer was washed with water and saturated brie, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to a silica gel column chromatography (ethyl acetate:hexane=1:4) to obtain the present compound 40 represented by the following formula 0.31 g.

##STR00098##

Present compound 40: .sup.1H-NMR (CDCl.sub.3) δ: 7.44-7.29 (5H, m), 7.29 (1H, s), 7.05 (1H, d), 6.53 (1H, dd), 6.41 (1H, d), 4.98 (2H, s), 3.84 (3H, s), 3.69 (3H, s), 2.27 (3H, s).

Preparation Example 2-1

[0479] The compound which was prepared according to the Preparation Example 2 and its physical property value are shown below.

[0480] A compound represented by formula (1a1) wherein a combination of E, R.sup.1 and L represents any combinations indicated in [Table 2-1].

TABLE-US-00010 TABLE 2-1 Present compound E R.sup.1 L 41 [00099] Me O 42 [00100] Me O 43 [00101] Me O 44 [00102] Me O 45 [00103] Me O
Present compound 41: .sup.1H-NMR (CDCl.sub.3) δ: 7.70-7.64 (2H, m), 7.61 (1H, t), 7.41 (1H, t), 7.32 (1H, s), 7.06 (1H, d), 6.55 (1H, dd), 6.42 (1H, d), 5.19 (2H, s), 3.87 (3H, s), 3.69 (3H, s), 2.28 (3H, s).
Present compound 42: .sup.1H-NMR (CDCl.sub.3) δ: 7.74 (1H, s), 7.66-7.58 (2H, m), 7.48 (1H, t), 7.32 (1H, s), 7.06 (1H, d), 6.49 (1H, dd), 6.39 (1H, d), 5.00 (2H, s), 3.87 (3H, s), 3.70 (3H, s), 2.28 (3H, s).
Present compound 43: .sup.1H-NMR (CDCl.sub.3) δ: 7.67 (2H, d), 7.52 (2H, d), 7.30 (1H, s), 7.06 (1H, d), 6.48 (1H, dd), 6.38 (1H, d), 5.04 (2H, s), 3.86 (3H, s), 3.70 (3H, s), 2.28 (3H, s).
Present compound 44: .sup.1H-NMR (CDCl.sub.3) δ: 7.31 (1H, s), 7.06 (1H, d), 6.52 (1H, dd), 6.41 (1H, d), 4.61 (2H, d), 3.86 (3H, s), 3.70 (3H, s), 2.50 (1H, t), 2.28 (3H, s).
Present compound 45: .sup.1H-NMR (CDCl.sub.3) δ: 7.33 (1H, s), 7.05 (1H, d), 6.44 (1H, dd), 6.32 (1H, d), 4.00 (2H, t), 3.88 (3H, s), 3.72 (3H, s), 2.57 (2H, t), 2.28 (3H, s), 2.14-2.05 (2H, m).

Preparation Example 3

[0481] To a mixture of the intermediate compound A1 0.20 g, potassium carbonate 0.15 g, and DMF 5 mL was added dimethyl carbamoyl chloride 0.09 mL at room temperature, and the mixture was stirred for 19 hours. To the resulting mixture was added saturated ammonium chloride aqueous solution, and the mixture was extracted with ethyl acetate. The resulting organic layer was washed with water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to a silica gel column chromatography (ethyl acetate:hexane=1:3) to obtain the present compound 46 represented by the following formula 0.08 g.

##STR00104##

Present compound 46: .sup.1H-NMR (CDCl.sub.3) δ: 7.30 (1H, s), 7.10 (1H, d), 6.68 (1H, dd), 6.50 (1H, d), 3.86 (3H, s), 3.70 (3H, s), 3.06 (3H, s), 2.98 (3H, s), 2.31 (3H, s).

Preparation Example 3-1

[0482] The compound which was prepared according to the Preparation Example 3 and its physical property value are shown below.

[0483] A compound represented by formula (1a1) wherein a combination of E, R.sup.1 and L represents any combinations indicated in [Table 3-1].

TABLE-US-00011 TABLE 3-1 Present compound E R.sup.1 L 47 [00105] Me O 48 [00106] Me O 49 [00107] Me O 50 [00108] Me CH.sub.2 51 [00109] Me O 52 [00110] Me O 89 [00111] Me CH.sub.2 90 [00112] Me CH.sub.2
Present compound 47: .sup.1H-NMR (CDCl.sub.3) δ: 7.30 (1H, s), 7.10 (1H, d), 6.71-6.65 (1H, m), 6.52-6.49 (1H, m), 3.86 (3H, s), 3.70 (3H, s), 3.47-3.34 (2H, in), 3.03 (1.5H, s), 2.96 (1.5H, s), 2.31 (3H, s), 1.24-1.13 (3H, m).
Present compound 48: .sup.1H-NMR (CDCl.sub.3) δ: 7.30 (1H, s), 7.10 (1H, d), 6.68 (1H, dd), 6.51 (1H, d), 3.86 (3H, s), 3.71 (3H, s), 3.44-3.32 (4H, m), 2.31 (3H, s), 1.25-1.14 (6H, m)).
Present compound 49: .sup.1H-NMR (CDCl.sub.3) δ: 7.42-7.30 (4H, m), 7.29 (1H, s), 7.27-7.22 (1H, m), 7.09 (1H, d), 6.75-6.61 (1H, br m), 6.51 (1H, br s), 3.85 (3H, s), 3.69 (3H, s), 3.40 (3H, s), 2.30 (3H, s).
Present compound 50: .sup.1H-NMR (CDCl.sub.3) δ: 7.45 (1H, s), 7.41-7.32 (4H, m), 7.25-7.21 (1H, m), 7.06 (1H, d), 6.86-6.77 (2H, m), 3.83 (3H, s), 3.65 (3H, s), 3.51 (2H, s), 3.41 (3H, s), 2.30 (3H, s).
Present compound 51: .sup.1H-NMR (CDCl.sub.3) δ: 7.30 (1H, s), 7.10 (1H, d), 6.71 (1H, dd), 6.54 (1H, d), 3.86 (3H, s), 3.70 (3H, s), 3.52 (2H, t), 3.45 (2H, t), 2.31 (3H, s), 1.98-1.85 (4H, m).
Present compound 52: .sup.1H-NMR (CDCl.sub.3) δ: 7.30 (1H, s), 7.10 (1H, d), 6.67 (1H, dd), 6.50 (1H, d), 3.86 (3H, s), 3.70 (3H, s), 3.62-3.43 (4H, br m), 2.30 (3H, s), 1.69-1.52 (6H, m).
Present compound 89: .sup.1H-NMR (CDCl.sub.3) δ: 7.46 (1H, s), 7.07 (1H, d), 6.85-6.80 (2H, m), 3.83 (3H, s), 3.66 (3H, s), 3.52 (2H, s), 3.07 (3H, s), 2.99 (3H, s), 2.31 (3H, s).
Present compound 90: .sup.1H-NMR (CDCl.sub.3) δ: 7.46 (1H, s), 7.07 (1H, d), 6.87-6.80 (2H, m), 3.83 (3H, s), 3.67 (3H, s), 3.53 (2H, s), 3.46-3.32 (4H, m), 2.31 (3H, s), 1.27-1.15 (6H, m).

Preparation Example 4

[0484] To a mixture of the intermediate compound A1 0.25 g, triphosgene 0.10 g, and chloroform 5 mL was added N,N-diisopropylethylamine 0.18 mL at room temperature, and the mixture was stirred for 2 hours. To the resulting mixture were added propyl amine 0.11 mL and N,N-diisopropylethylamine 0.27 mL successively, and the mixture was stirred for 16 hours. Water was added to the resulting mixture, and the mixture was extracted with ethyl acetate. The resulting organic layer was washed with water and saturated brine successively, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to a silica gel column chromatography (ethyl acetate:hexane=1:4) to obtain the present compound 53 represented by the following formula 0.18 g.

##STR00113##

Present compound 53: .sup.1H-NMR (CDCl.sub.3) δ: 7.29 (1H, s), 7.10 (1H, d), 6.69 (1H, dd), 6.52 (1H, d), 4.97-4.88 (1H, br m), 3.85 (3H, s), 3.70 (3H, s), 3.20 (2H, q), 2.30 (3H, s), 1.63-1.52 (2H, m), 0.95 (3H, t).

Preparation Example 4-1

[0485] The compound which was prepared according to the Preparation Example 4 and its physical property value are shown below.

[0486] A compound represented by formula (1a1) wherein a combination of E, R.sup.1 and L represents any combinations indicated in [Table 4-1].

TABLE-US-00012 TABLE 4-1 Present compound E R.sup.1 L 54 [00114] Me O 55 [00115] Me O 56 [00116] Me O 57 [00117] Me O 58 [00118] Me O 59 [00119] Me O
Present compound 54: .sup.1H-NMR (CDCl.sub.3) δ: 7.29 (1H, s), 7.10 (1H, d), 6.69 (1H, dd), 6.52 (1H, d), 4.94-4.83 (1H, br m), 3.85 (3H, s), 3.70 (3H, s), 3.24 (2H, q), 2.30 (3H, s), 1.58-1.48 (2H, m), 1.43-1.32 (2H, m), 0.94 (3H, t).
Present compound 55: .sup.1H-NMR (CDCl.sub.3) δ: 7.29 (1H, s), 7.10 (1H, d), 6.69 (1H, dd), 6.52 (1H, d), 4.93-4.85 (1H, br m), 3.85 (3H, s), 3.70 (3H, s), 3.23 (2H, q), 2.30 (3H, s), 1.59-1.50 (2H, m), 1.38-1.28 (4H, m), 0.91 (3H, t).
Present compound 56: .sup.1H-NMR (CDCl.sub.3) δ: 7.29 (1H, s), 7.09 (1H, d), 6.69 (1H, dd), 6.52 (1H, d), 4.83-4.76 (1H, br m), 3.85 (3H, s), 3.70 (3H, s), 3.58-3.47 (1H, m), 2.30 (3H, s), 2.02-1.94 (2H, m), 1.77-1.66 (2H, m), 1.65-1.57 (1H, m), 1.42-1.29 (2H, m), 1.26-1.12 (3H, m).
Present compound 57: .sup.1H-NMR (CDCl.sub.3) δ: 7.30 (1H, s), 7.10 (1H, d), 6.71-6.63 (1H, m), 6.52-6.47 (1H, m), 3.86 (3H, s), 3.70 (3H, s), 3.38-3.25 (2H, m), 3.03 (1.4H, s), 2.97 (1.6H, s), 2.31 (3H, s), 1.68-1.58 (2H, m), 0.98-0.90 (3H, m).
Present compound 58: .sup.1H-NMR (CDCl.sub.3) δ: 7.30 (1H, s), 7.10 (1H, d), 6.71-6.64 (1H, m), 6.51-6.49 (1H, m), 3.86 (3H, s), 3.70 (3H, s), 3.41-3.28 (2H, m), 3.03 (1.4H, s), 2.96 (1.6H, s), 2.30 (3H, s), 1.64-1.52 (2H, m), 1.41-1.30 (2H, m), 0.98-0.92 (3H, m).
Present compound 59: .sup.1H-NMR (CDCl.sub.3) δ: 7.30 (1H, s), 7.13 (1H, d), 6.71 (1H, dd), 6.55 (1H, d), 3.86 (3H, s), 3.78 (3H, s), 3.70 (3H, s), 3.26 (3H, s), 2.32 (3H, s).

Preparation Example 5

[0487] To a mixture of the intermediate compound A1 0.20 g, propionyl chloride 0.09 mL, and chloroform 5 mL was added triethylamine 0.17 mL, and the mixture was stirred for 16 hours. To the resulting mixture was added water, and the mixture was extracted with ethyl acetate. The resulting organic layer was washed with water and saturated brine successively, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to a silica gel column chromatography (ethyl acetate:hexane=1:4) to obtain the present compound 60 represented by the following formula 0.18 g.

##STR00120##

Present compound 60: .sup.1H-NMR (CDCl.sub.3) δ: 7.31 (1H, s), 7.13 (1H, d), 6.66 (1H, dd), 6.48 (1H, d), 3.86 (3H, s), 3.71 (3H, s), 2.54 (2H, q), 2.32 (3H, s), 1.24 (3H, t).

Preparation Example 5-1

[0488] The compound which was prepared according to the Preparation Example 5 and its physical property value are shown below.

[0489] A compound represented by formula (1a1) wherein a combination of E, R.sup.1 and L represents any combinations indicated in [Table 5-1].

TABLE-US-00013 TABLE 5-1 Present compound E R.sup.1 L 61 [00121] Me O 62 [00122] Me O 63 [00123] Me O 64 [00124] Me O 65 [00125] Me O 66 [00126] Me O 67 [00127] Me O
Present compound 61: .sup.1H-NMR (CDCl.sub.3) δ: 7.30 (1H, s), 7.11 (1H, d), 6.63 (1H, dd), 6.44 (1H, d), 3.85 (3H, s), 3.70 (3H, s), 2.49 (1H, tt), 2.31 (3H, s), 2.07-1.98 (2H, m), 1.85-1.75 (2H, m), 1.71-1.63 (1H, m), 1.61-1.47 (2H, m), 1.39-1.20 (3H, m).
Present compound 62: .sup.1H-NMR (CDCl.sub.3) δ: 8.17 (2H, d), 7.62 (1H, t), 7.49 (2H, t), 7.31 (1H, s), 7.18 (1H, d), 6.79 (1H, dd), 6.60 (1H, d), 3.87 (3H, s), 3.71 (3H, s), 2.35 (3H, s).
Present compound 63: .sup.1H-NMR (CDCl.sub.3) δ: 7.31 (1H, s), 7.14 (1H, d), 6.76 (1H, dd), 6.57 (1H, d), 4.29 (2H, q), 3.87 (3H, s), 3.71 (3H, s), 2.32 (3H, s), 1.37 (3H, t).
Present compound 64: .sup.1H-NMR (CDCl.sub.3) δ: 7.31 (1H, s), 7.12 (1H, d), 6.77 (1H, dd), 6.55 (1H, d), 3.86 (3H, s), 3.70 (3H, s), 2.31 (3H, s), 1.54 (9H, s).
Present compound 65: .sup.1H-NMR (CDCl.sub.3) δ: 7.33 (1H, s), 7.17 (1H, d), 6.83 (1H, dd), 6.68 (1H, d), 3.88 (3H, s), 3.72 (3H, s), 3.07 (3H, s), 2.34 (3H, s).
Present compound 66: .sup.1H-NMR (CDCl.sub.3) δ: 7.33 (1H, s), 7.16 (1H, d), 6.81 (1H, dd), 6.66 (1H, d), 3.88 (3H, s), 3.72 (3H, s), 3.18-3.12 (2H, m), 2.33 (3H, s), 2.03-1.91 (2H, m), 1.09 (3H, t).
Present compound 67: .sup.1H-NMR (CDCl.sub.3) δ: 7.80 (2H, t), 7.64 (1H, t), 7.50 (2H, t), 7.25 (1H, s), 7.01 (1H, d), 6.46 (1H, dd), 6.42 (1H, d), 3.85 (3H, s), 3.70 (3H, s), 2.28 (3H, s).

Preparation Example 6

[0490] To a mixture of the intermediate compound A1 0.18 g, dimethyl carbamoyl chloride 0.11 g and DMF 5 mL was added sodium hydride (60%, oily) 0.05 g at room temperature, and the mixture was stirred for 4 hours. To the resulting mixture was added saturated ammonium chloride aqueous solution, and the mixture was extracted with ethyl acetate. The resulting organic layer was washed with water and saturated brine successively, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to a silica gel column chromatography (ethyl acetate:hexane=1:3) to obtain the present compound 68 represented by the following formula 0.12 g.

##STR00128##

Present compound 68: .sup.1H-NMR (CDCl.sub.3) δ: 7.30 (1H, s), 7.15 (1H, d), 6.63 (1H, dd), 6.48 (1H, d), 3.86 (3H, s), 3.71 (3H, s), 3.44 (3H, s), 3.31 (3H, s), 2.33 (3H, s).

Preparation Example 6-1

[0491] The compound which was prepared according to the Reference Preparation Example 6 and its physical property value are shown below.

[0492] A compound represented by formula (1a1) wherein a combination of E, R.sup.1 and L represents any combinations indicated in [Table 6-1].

TABLE-US-00014 TABLE 6-1 Present compound E R.sup.1 L 69 [00129] Me O 70 [00130] Me O
Present compound 69: .sup.1H-NMR (CDCl.sub.3) δ: 7.33 (1H, s), 7.14 (1H, d), 6.83 (1H, dd), 6.69 (1H, d), 3.88 (3H, s), 3.71 (3H, s), 2.90 (6H, s), 2.32 (3H, s).
Present compound 70: .sup.1H-NMR (CDCl.sub.3) δ: 7.33 (1H, s), 7.13 (1H, d), 6.81 (1H, dd), 6.67 (1H, d), 3.87 (3H, s), 3.71 (3H, s), 3.30 (4H, q), 2.32 (3H, s), 1.16 (6H, t).

Preparation Example 7

[0493] To a mixture of the intermediate compound B1 0.19 g, potassium carbonate 0.10 g and DMF 5 mL was added iodomethane 0.10 mL at 0° C., and the mixture was stirred for 1 hour. To the resulting mixture was added water, and the mixture was extracted with MTBE. The resulting organic layer was washed with water and saturated brine successively, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to a silica gel column chromatography (ethyl acetate:hexane=1:4) to obtain the present compound 40 represented by the following formula 0.09 g.

Preparation Example 8

[0494] A mixture of the intermediate compound D2 0.03 g, benzyl alcohol 0.02 g, palladium(II) acetate 0.001 g, 2-(di-t-butylphosphino)-1,1′-binapthyl 0.002 g, cesium carbonate 0.08 g and toluene 2 mL was stirred at 40° C. for 15 hours. Water was added to the resulting mixture, and the mixture was extracted with ethyl acetate. The resulting organic layer was dried over anhydrous sodium sulfate, and concentrated under reduced pressure to obtain a crude product 0.03 g containing the present compound 40. Present compound 40: LCMS: 329 [M+H].sup.+, RT=2.08 min.

Preparation Example 9

[0495] A mixture of the intermediate compound D1 0.05 g, benzyl alcohol 0.04 g and tBuBrettPhos Pd G3 0.01 g, sodium tert-butoxide 0.03 g, and dioxane 2 mL was stirred at 80° C. for 4 hours. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The resulting organic layer was dried over anhydrous sodium sulfate, and concentrated under reduced pressure to obtain a crude product 0.05 g containing the present compound 28. Present compound 28: LCMS: 327 [M+H].sup.+, RT=2.22 min.

[0496] Next, the present compounds which were prepared according to the Preparation Examples described in the Examples, and the processes described in the Detailed Description, and their intermediate compounds are shown below.

[0497] A compound represented by formula (1A):

##STR00131##

wherein R.sup.1 represents a methyl group, L represents an oxygen atom, and R.sup.X1 represents any substituents selected from Group X
(hereinafter, referred to as Compound Class SX1).
Group X: a group consisting of Et, Pr, i-Pr, (CH.sub.2).sub.3CH.sub.3, CH.sub.2CH(CH.sub.3).sub.2, CH(CH.sub.3)CH.sub.2CH.sub.3, C(CH.sub.3).sub.3, CH.sub.2c-Pr, (CH.sub.2).sub.4CH.sub.3, (CH.sub.2).sub.2CH(CH.sub.3).sub.2, CH(CH.sub.3) (CH.sub.2).sub.2CH.sub.3, CH(CH.sub.2CH.sub.3)CH.sub.2C H.sub.3, CH.sub.2CH(CH.sub.3)CH.sub.2CH.sub.3, C(CH.sub.3) 2CH.sub.2CH.sub.3, CH.sub.2C(CH.sub.3).sub.3, CH.sub.2c-Bu, CH.sub.2c-Pen, CH.sub.2c-Hex, (CH.sub.2).sub.2c-Pr, (1-methylcyclopropyl)methyl, (2-methylcyclopropyl)methyl, 1-cyclopropylethyl, (CH.sub.2).sub.3c-Pr, (CH.sub.2).sub.5CH.sub.3, (CH.sub.2).sub.3CH(CH.sub.3).sub.2, (CH.sub.2).sub.2CH(CH.sub.3)CH.sub.2CH.sub.3, CH.sub.2CH(CH.sub.3) (CH.sub.2).sub.2CH.sub.3, CH(CH.sub.3) (CH.sub.2).sub.3CH.sub.3, CH.sub.2CH(CH.sub.2CH.sub.3).sub.2, heptyl, octyl, nonyl, decyl, CH.sub.2CH═CH.sub.2, CH.sub.2CH═CHCH.sub.3, CH.sub.2CH═C(CH.sub.3), CH.sub.2CH═CF.sub.2, CH.sub.2CH═CCl.sub.2, CH.sub.2CH═CHCH.sub.2CH.sub.3, CH.sub.2CH═CH(CH.sub.2).sub.2CH.sub.3, CH.sub.2C(CH.sub.3)═CH.sub.2, CH.sub.2C(CH.sub.3)═CHCH.sub.3, CH.sub.2C(CH.sub.3)═C(CH.sub.3).sub.2, CH.sub.2C(CH.sub.3)═CHCH.sub.2CH.sub.3, CH.sub.2C(CH.sub.3)═CH(CH.sub.2).sub.2CH.sub.3, CH.sub.2CF═CH.sub.2, CH.sub.2CF═CHCH.sub.3, CH.sub.2CF═C(CH.sub.3), CH.sub.2CF═CF.sub.2, CH.sub.2CF═CHCH.sub.2CH.sub.3, CH.sub.2CF═CH(CH.sub.2).sub.2CH.sub.3, CH.sub.2CCl═CH.sub.2, CH.sub.2CCl═CHCH.sub.3, CH.sub.2CCl═C(CH.sub.3).sub.2, CH.sub.2CCl═CCl.sub.2, CH.sub.2CCl═CHCH.sub.2CH.sub.3, CH.sub.2CCl═CH(CH.sub.2).sub.2CH.sub.3, (CH.sub.2).sub.2CH═CH.sub.2, (CH.sub.2).sub.2CH═CHCH.sub.3, (CH.sub.2).sub.2CH═CHCH.sub.2CH.sub.3, (CH.sub.2).sub.2CH═C(CH.sub.3).sub.2, (CH.sub.2).sub.2C(CH.sub.3)═CH.sub.2, (CH.sub.2).sub.2C(CH.sub.3)═CHCH.sub.3, (CH.sub.2).sub.2C(CH.sub.3)═CHCH.sub.2CH.sub.3, (CH.sub.2).sub.2C(CH.sub.3)═C(CH.sub.3).sub.2, (CH.sub.2).sub.3CH═CH.sub.2, (CH.sub.2).sub.3C(CH.sub.3)═CH.sub.2, (CH.sub.2).sub.4CH═CH.sub.2, (CH.sub.2).sub.4C(CH.sub.3)═CH.sub.2, CH.sub.2C≡CH, CH.sub.2C═CCH.sub.3, CH.sub.2C═CCH.sub.2CH.sub.3, CH.sub.2C≡Cc-Pr, CH.sub.2C≡CPh, (CH.sub.2).sub.2C═CH, (CH.sub.2).sub.2C═CCH.sub.3, (CH.sub.2).sub.2C═CCH.sub.2CH.sub.3, (CH.sub.2).sub.2C≡Cc-Pr, (CH.sub.2).sub.2C≡CPh, (CH.sub.2).sub.3C═CH, (CH.sub.2).sub.3C═CCH.sub.3, (CH.sub.2).sub.3C═CCH.sub.2CH.sub.3, (CH.sub.2).sub.3C═Cc-Pr, (CH.sub.2).sub.3C≡CPh, CH.sub.2Cl, CH.sub.2Br, CH.sub.2CN, CH.sub.2OCH.sub.3, CH.sub.2OCH.sub.2CH.sub.3, CH.sub.2O(CH.sub.2).sub.2CH.sub.3, CH.sub.2OPh, CH.sub.2SCH.sub.3, CH.sub.2S(O)CH.sub.3, CH.sub.2S(O).sub.2CH.sub.3, CH.sub.2SCH.sub.2CH.sub.3, CH.sub.2S(O)CH.sub.2CH.sub.3, CH.sub.2S(O).sub.2CH.sub.2CH.sub.3, CH.sub.2S(CH.sub.2).sub.2CH.sub.3, CH.sub.2S(O)(CH.sub.2).sub.2CH.sub.3, CH.sub.2S(O).sub.2(CH.sub.2).sub.2CH.sub.3, CH.sub.2SPh, CH.sub.2S(O) Ph, CH.sub.2S(O).sub.2Ph, CH.sub.2C(O)CH.sub.3, CH.sub.2C(O)CH.sub.2CH.sub.3, CH.sub.2C(O)Ph, CH.sub.2C(O)NH.sub.2, CH.sub.2C(O)NHCH.sub.3, CH.sub.2C(O)N(CH.sub.3).sub.2, CH.sub.2C(O)NHPh, CH.sub.2C(O)N(CH.sub.3)Ph, CH.sub.2C(O)OCH.sub.3, CH.sub.2C(O)OCH.sub.2CH.sub.3, CH.sub.2OC(O)Ph, CH.sub.2OC(O)OCH.sub.3, CH.sub.2OC(O)OCH.sub.2CH.sub.3, CH.sub.2OC(O) OPh, CH.sub.2OC(O)NHCH.sub.3, CH.sub.2OC(O)NHCH.sub.2CH.sub.3, CH.sub.2C(O)NHPh, CH.sub.2OC(O)N(CH.sub.3).sub.2, CH.sub.2OC(O)N(CH.sub.3)CH.sub.2CH.sub.3, CH.sub.2OC(O)N(CH.sub.3)Ph, CH.sub.2OC(O)N(CH.sub.2CH.sub.3).sub.2, CH.sub.2 (2-oxiranyl), CH.sub.2(2-tetrahydrofuranyl), CH.sub.2(2-tetrahydropyranyl), CH.sub.2CH═NOCH.sub.3, CH.sub.2CH═NOCH.sub.2CH.sub.3, CH.sub.2CH═NOCH.sub.2Ph, CH.sub.2C(CH.sub.3)═NOCH.sub.3, CH.sub.2C(CH.sub.3)═NOCH.sub.2CH.sub.3, CH.sub.2C(CH.sub.3)═NOCH.sub.2Ph, (CH.sub.2).sub.2F, CH.sub.2CF.sub.3, (CH.sub.2).sub.2Cl, CH.sub.2CCl.sub.3, (CH.sub.2).sub.2Br, (CH.sub.2).sub.2I, CH.sub.2Si(CH.sub.3).sub.3, (CH.sub.2).sub.2CF.sub.3, (CH.sub.2).sub.2CN, (CH.sub.2).sub.2NO.sub.2, (CH.sub.2).sub.2Si(CH.sub.3).sub.3, (CH.sub.2).sub.2OCH.sub.3, (CH.sub.2).sub.2OCH.sub.2CH.sub.3, (CH.sub.2).sub.2SCH.sub.3, (CH.sub.2).sub.2SCH.sub.2CH.sub.3, (CH.sub.2).sub.2SPh, (CH.sub.2).sub.2S(O)CH.sub.3, (CH.sub.2).sub.2S(O)CH.sub.2CH.sub.3, (CH.sub.2).sub.2S(O)Ph, (CH.sub.2).sub.2S(O).sub.2CH.sub.3, (CH.sub.2).sub.2S(O).sub.2CH.sub.2CH.sub.3, (CH.sub.2).sub.2S(O).sub.2Ph, (CH.sub.2).sub.2NHCH.sub.3, (CH.sub.2).sub.2N(CH.sub.3).sub.2, (CH.sub.2).sub.2NHPh, (CH.sub.2).sub.2NHCH.sub.2Ph, (CH.sub.2).sub.2N(CH.sub.3)CH.sub.2Ph, (CH.sub.2).sub.2C(O)CH.sub.3, (CH.sub.2).sub.2C(O)CH.sub.2CH.sub.3, (CH.sub.2).sub.2C(O)Ph, (CH.sub.2).sub.2S(O).sub.2NHCH.sub.3, (CH.sub.2).sub.2S(O).sub.2N(CH.sub.3).sub.2, (CH.sub.2).sub.2S(O).sub.2NHPh, (CH.sub.2).sub.2S(O).sub.2N(CH.sub.3)Ph, (CH.sub.2).sub.2C(O)NH.sub.2, (CH.sub.2).sub.2C(O)NHCH.sub.3, (CH.sub.2).sub.2C(O)N(CH.sub.3).sub.2, (CH.sub.2).sub.2C(O)NHPh, (CH.sub.2).sub.2C(O)N(CH.sub.3)Ph, (CH.sub.2).sub.2C(O)OCH.sub.3, (CH.sub.2).sub.2C(O)OCH.sub.2CH.sub.3, (CH.sub.2).sub.2NHC(O)CH.sub.3, (CH.sub.2).sub.2NHC(O)CH.sub.2CH.sub.3, (CH.sub.2).sub.2NHC(O) Ph, (CH.sub.2).sub.2NCH.sub.3C(O)CH.sub.3, (CH.sub.2).sub.2NCH.sub.3C(O)CH.sub.2CH.sub.3, (CH.sub.2).sub.2NCH.sub.3C(O) Ph, (CH.sub.2).sub.2NHC(O)OCH.sub.3, (CH.sub.2).sub.2NHC(O)OCH.sub.2CH.sub.3, (CH.sub.2).sub.2NHC(O)OPh, (CH.sub.2).sub.2NCH.sub.3C(O)OCH.sub.3, (CH.sub.2).sub.2NCH.sub.3C(O)OCH.sub.2CH.sub.3, (CH.sub.2).sub.2NCH.sub.3C(O)OPh, (CH.sub.2).sub.2NHC(O)NHCH.sub.3, (CH.sub.2).sub.2NHC(O)NHCH.sub.2CH.sub.3, (CH.sub.2).sub.2NHC(O)NHPh, (CH.sub.2).sub.2NHC(O)N(CH.sub.3).sub.2, (CH.sub.2).sub.2NHC(O)N(CH.sub.3)CH.sub.2CH.sub.3, (CH.sub.2).sub.2NHC(O)N(CH.sub.3)Ph, (CH.sub.2).sub.2NHC(O)N(CH.sub.2CH.sub.3).sub.2, (CH.sub.2).sub.2NCH.sub.3C(O)NHCH.sub.3, (CH.sub.2).sub.2NCH.sub.3C(O)NHCH.sub.2CH.sub.3, (CH.sub.2).sub.2NCH.sub.3C(O)NHPh, (CH.sub.2).sub.2NCH.sub.3C(O)N(CH.sub.3).sub.2, (CH.sub.2).sub.2NCH.sub.3C(O)N(CH.sub.3)CH.sub.2CH.sub.3, (CH.sub.2).sub.2NCH.sub.3C(O)N(CH.sub.3)Ph, (CH.sub.2).sub.2NCH.sub.3C(O)N(CH.sub.2CH.sub.3).sub.2, (CH.sub.2).sub.2OC(O)CH.sub.3, (CH.sub.2).sub.2OC(O)CH.sub.2CH.sub.3, (CH.sub.2).sub.2OC(O)Ph, (CH.sub.2).sub.2OC(O)OCH.sub.3, (CH.sub.2).sub.2OC(O)OCH.sub.2CH.sub.3, (CH.sub.2).sub.2OC(O)OPh, (CH.sub.2).sub.2OC(O)NHCH.sub.3, (CH.sub.2).sub.2OC(O)NHCH.sub.2CH.sub.3, (CH.sub.2).sub.2OC(O) NHPh, (CH.sub.2).sub.2OC(O)N(CH.sub.3).sub.2, (CH.sub.2).sub.2OC(O)N(CH.sub.3)CH.sub.2CH.sub.3, (CH.sub.2).sub.2OC(O)N(CH.sub.3) Ph, (CH.sub.2).sub.2OC(O)N(CH.sub.2CH.sub.3).sub.2, (CH.sub.2).sub.2S(O).sub.2NHCH.sub.3, (CH.sub.2).sub.2S(O).sub.2NHCH.sub.2CH.sub.3, (CH.sub.2).sub.2S(O).sub.2NHPh, (CH.sub.2).sub.2S(O).sub.2N(CH.sub.3).sub.2, (CH.sub.2).sub.2S(O).sub.2N(CH.sub.3)CH.sub.2CH.sub.3, (CH.sub.2).sub.2S(O).sub.2N(CH.sub.3)Ph, (CH.sub.2).sub.2S(O).sub.2N(CH.sub.2CH.sub.3).sub.2, (CH.sub.2).sub.3F, (CH.sub.2).sub.3Cl, (CH.sub.2).sub.3Br, (CH.sub.2).sub.3I, (CH.sub.2).sub.3CF.sub.3, (CH.sub.2).sub.3CN, (CH.sub.2).sub.3NO.sub.2, (CH.sub.2).sub.3Si(CH.sub.3).sub.3, (CH.sub.2).sub.3OCH.sub.3, (CH.sub.2).sub.3OCH.sub.2CH.sub.3, (CH.sub.2).sub.3SCH.sub.3, (CH.sub.2).sub.3SCH.sub.2CH.sub.3, (CH.sub.2).sub.3NHCH.sub.3, (CH.sub.2).sub.3N(CH.sub.3).sub.2, (CH.sub.2).sub.4F, (CH.sub.2).sub.4Cl, (CH.sub.2).sub.4CF.sub.3, (CH.sub.2).sub.4CN, (CH.sub.2).sub.4NO.sub.2, (CH.sub.2).sub.4Ph, (CH.sub.2).sub.4OCH.sub.3, (CH.sub.2).sub.4SCH.sub.3, (CH.sub.2).sub.4NHCH.sub.3, (CH.sub.2).sub.4N(CH.sub.3).sub.2, (CH.sub.2).sub.5F, (CH.sub.2).sub.5Cl, (CH.sub.2).sub.5CF.sub.3, (CH.sub.2).sub.5CN, (CH.sub.2).sub.5NO.sub.2, (CH.sub.2).sub.5Ph, (CH.sub.2).sub.50CH.sub.3, (CH.sub.2).sub.5SCH.sub.3, (CH.sub.2).sub.5NHCH.sub.3, (CH.sub.2).sub.5N(CH.sub.3).sub.2, (CH.sub.2).sub.6F, (CH.sub.2).sub.6Cl, (CH.sub.2).sub.6CF.sub.3, (CH.sub.2).sub.6CN, (CH.sub.2).sub.6NO.sub.2, (CH.sub.2).sub.6Ph, (CH.sub.2).sub.6OCH.sub.3, (CH.sub.2).sub.6SCH.sub.3, (CH.sub.2).sub.6NHCH.sub.3, (CH.sub.2).sub.6N(CH.sub.3).sub.2, CH.sub.2CF.sub.2CF.sub.3, (CH.sub.2).sub.2CF.sub.2CF.sub.3, CH.sub.2 (CF.sub.2).sub.2CF.sub.3, (CH.sub.2).sub.2CF(CF.sub.3).sub.2, (CH.sub.2).sub.2(CF.sub.2).sub.5CF.sub.3, CF.sub.3, CF.sub.2CHF(CF.sub.3), and CF.sub.2CHF(OCF.sub.3), CH.sub.2CF.sub.2CF.sub.2H.

[0498] The compound represented by formula (A1) wherein R.sup.1 represents a chlorine atom, L represents an oxygen atom, and R.sup.X1 represents any substituents selected from Group X (hereinafter, referred to as Compound Class SX2).

[0499] The compound represented by formula (1A) wherein R.sup.1 represents a methyl group, L represents CH.sub.2, and R.sup.X1 represents any substituents selected from Group X (hereinafter, referred to Compound Class SX3).

[0500] The compound represented by formula (1A) wherein R.sup.1 represents a chlorine atom, L represents CH.sub.2, and R.sup.X1 represents any substituents selected from Group X (hereinafter, referred to Compound Class SX4).

[0501] A compound represented by formula (1B):

##STR00132##

wherein, R.sup.1 represents a methyl group, L represents an oxygen atom, m is 1, and a combination of R.sup.X2, R.sup.X3, R.sup.X4, R.sup.X5, and R.sup.X6 represents any combinations described in a combination A below (hereinafter, referred to as Compound Class SX5).

[0502] The combination A consists of Substituent Nos. ZA1 to ZA311. The Substituents Nos. ZA1 to ZA311 represent any combinations of R.sup.X2, R.sup.X3, R.sup.X4, R.sup.X5, and R.sup.X6 respectively in the compound represented by formula (1B), the compound represented by formula (2B), and the compound represented by formula (3B), which are described below as [Substituent No. R.sup.X2, R.sup.X3, R.sup.X4, R.sup.X5, R.sup.X6]. For example, Substituent No. ZA2 represents a combination wherein R.sup.X2 represents a methyl group, and a combination of R.sup.X3, R.sup.X4, R.sup.X5, and R.sup.X6 represents a hydrogen atom.

Combination A

[0503] [ZA1;H,H,H,H,H], [ZA2;Me,H,H,H,H], [ZA3;F,H,H,H,H], [ZA4;Cl,H,H,H,H], [ZA5;OMe,H,H,H,H], [ZA6; CF.sub.3,H,H,H,H], [ZA7;H,Me,H,H,H], [ZA8;H,Et,H,H,H], [ZA9;H,Pr,H,H,H], [ZA10;H,i-Pr,H,H,H], [ZA11;H,t-Bu,H,H,H], [ZA12;H,OMe,H,H,H], [ZA13;H,OEt,H,H,H], [ZA14;H,OPr,H,H,H], [ZA15;H,Oi-Pr,H,H,H], [ZA16;H,CF.sub.3,H,H,H], [ZA17;H,CF.sub.2H,H,H,H], [ZA18;H,CFH.sub.2,H,H,H], [ZA19;H,F,H,H,H], [ZA20;H,Cl,H,H,H], [ZA21;H,Br,H,H,H], [ZA22;H,CN,H,H,H], [ZA23;H,Ph,H,H,H], [ZA24;H,OPh,H,H,H], [ZA25;H,c-Pr,H,H,H], [ZA26;H,c-Pen,H,H,H], [ZA27;H,c-Hex,H,H,H], [ZA28;H,H,Me,H,H], [ZA29;H,H,Et,H,H], [ZA30;H,H,Pr,H,H], [ZA31;H,H,i-Pr,H,H], [ZA32;H,H,t-Bu,H,H], [ZA33;H,H,OMe,H,H], [ZA34;H,H,OEt,H,H], [ZA35;H,H,OPr,H,H], [ZA36;H,H,Oi-Pr,H,H], [ZA37;H,H,CF.sub.3,H,H], [ZA38;H,H,CF.sub.2H,H,H], [ZA39;H,H,CFH.sub.2,H,H], [ZA40;H,H,F,H,H], [ZA41;H,H,Cl,H,H], [ZA42;H,H,Br,H,H], [ZA43;H,H,CN,H,H], [ZA44;H,H,Ph,H,H], [ZA45;H,H,OPh,H,H], [ZA46;H,H,c-Pr,H,H], [ZA47;H,H,c-Pen,H,H], [ZA48;H,H,c-Hex,H,H], [ZA49;H,H,H,H,F], [ZA50;Me,H,H,H,F], [ZA51;F,H,H,H,F], [ZA52;Cl,H,H,H,F], [ZA53;H,Me,H,H,F], [ZA54;H,Et,H,H,F], [ZA55;H,Pr,H,H,F], [ZA56;H,i-Pr,H,H,F], [ZA57;H,t-Bu,H,H,F], [ZA58;H,OMe,H,H,F], [ZA59;H,OEt,H,H,F], [ZA60;H,OPr,H,H,F], [ZA61;H,Oi-Pr,H,H,F], [ZA62;H,CF.sub.3,H,H,F], [ZA63;H,CF.sub.2H,H,H,F], [ZA64;H,CFH.sub.2,H,H,F], [ZA65;H,F,H,H,F], [ZA66;H,Cl,H,H,F], [ZA67;H,Br,H,H,F], [ZA68;H,CN,H,H,F], [ZA69;H,Ph,H,H,F], [ZA70;H,OPh,H,H,F], [ZA71;H,c-Pr,H,H,F], [ZA72;H,c-Pen,H,H,F], [ZA73;H,c-Hex,H,H,F], [ZA74;H,H,Me,H,F], [ZA75;H,H,Et,H,F], [ZA76;H,H,Pr,H,F], [ZA77;H,H,i-Pr,H,F], [ZA78;H,H,t-Bu,H,F], [ZA79;H,H,OMe,H,F], [ZA80;H,H,OEt,H,F], [ZA81;H,H,OPr,H,F], [ZA82;H,H,Oi-Pr,H,F], [ZA83;H,H,CF.sub.3,H,F], [ZA84;H,H,CF.sub.2H,H,F], [ZA85;H,H,CFH.sub.2,H,F], [ZA86;H,H,F,H,F], [ZA87;H,H,Cl,H,F], [ZA88;H,H,Br,H,F], [ZA89;H,H,CN,H,F], [ZA90;H,H,Ph,H,F], [ZA91;H,H,OPh,H,F], [ZA92;H,H,c-Pr,H,F], [ZA93;H,H,c-Pen,H,F], [ZA94;H,H,c-Hex,H,F], [ZA95;H,H,H,H,Cl], [ZA96;Me,H,H,H,Cl], [ZA97;F,H,H,H,Cl], [ZA98;Cl,H,H,H,Cl], [ZA99;H,Me,H,H,Cl], [ZA100;H,Et,H,H,Cl]
[ZA101;H,Pr,H,H,Cl], [ZA102;H,i-Pr,H,H,Cl], [ZA103;H,t-Bu,H,H,Cl], [ZA104;H,OMe,H,H,Cl], [ZA105;H,OEt,H,H,Cl], [ZA106;H,OPr,H,H,Cl], [ZA107;H,Oi-Pr,H,H,Cl], [ZA108;H,CF.sub.3,H,H,Cl], [ZA109;H,CF.sub.2H,H,H,Cl], [ZA110;H,CFH,H,H,Cl], [ZA111;H,F,H,H,Cl], [ZA112;H,Cl,H,H,Cl], [ZA113;H,Br,H,H,Cl], [ZA114;H,CN,H,H,Cl], [ZA115;H,Ph,H,H,Cl], [ZA116;H,OPh,H,H,Cl], [ZA117;H,c-Pr,H,H,Cl], [ZA118;H,c-Pen,H,H,Cl], [ZA119;H,c-Hex,H,H,Cl], [ZA120;H,H,Me,H,Cl], [ZA121;H,H,Et,H,Cl], [ZA122;H,H,Pr,H,Cl], [ZA123;H,H,i-Pr,H,Cl], [ZA124;H,H,t-Bu,H,Cl], [ZA125;H,H,OMe,H,Cl], [ZA126;H,H,OEt,H,Cl], [ZA127;H,H,OPr,H,Cl], [ZA128;H,H,Oi-Pr,H,Cl], [ZA129;H,H,CF.sub.3,H,Cl], [ZA130;H,H,CF.sub.1H,H,Cl], [ZA131;H,H,CFH.sub.2,H,Cl], [ZA132;H,H,F,H,Cl], [ZA133;H,H,Cl,H,Cl], [ZA134;H,H,Br,H,Cl], [ZA135;H,H,CN,H,Cl], [ZA136;H,H,Ph,H,Cl], [ZA137;H,H,OPh,H,Cl], [ZA138;H,H,c-Pr,H,Cl], [ZA139;H,H,c-Pen,H,Cl], [ZA140;H,H,c-Hex,H,Cl], [ZA141;H,H,H,H,Me], [ZA142;Me,H,H,H,Me], [ZA143;F,H,H,H,Me], [ZA144;Cl,H,H,H,Me], [ZA145;H,Me,H,H,Me], [ZA146;H,Et,H,H,Me], [ZA147;H,Pr,H,H,Me], [ZA148;H,i-Pr,H,H,Me], [ZA149;H,t-Bu,H,H,Me], [ZA150;H,OMe,H,H,Me], [ZA151;H,OEt,H,H,Me], [ZA152;H,OPr,H,H,Me], [ZA153;H,Oi-Pr,H,H,Me], [ZA154;H,CF.sub.3,H,H,Me], [ZA155;H,CF:H,H,H,Me], [ZA156;H,CFH.sub.2,H,H,Me], [ZA157;H,F,H,H,Me], [ZA158;H,Cl,H,H,Me], [ZA159;H,Br,H,H,Me], [ZA160;H,CN,H,H,Me], [ZA161;H,Ph,H,H,Me], [Z A162;H,OPh,H,H,Me], [ZA163;H,c-Pr,H,H,Me], [ZA164;H,c-Pen,H,H,Me], [ZA165;H,c-Hex,H,H,Me], [ZA166;H,H,Me,H,Me], [ZA167;H,H,Et,H,Me], [ZA168; H,H,Pr,H,Me], [ZA169;H,H,i-Pr,H,Me], [ZA170;H,H,t-Bu,H,Me], [ZA171;H,H,OMe,H,Me], [ZA172;H,H,OEt,H,Me], [ZA173;H,H,OPr,H,Me], [ZA174;H,H,Oi-Pr,H,Me], [ZA175;H,H,CF.sub.3,H,Me], [ZA176;H,H,CF.sub.2H,H,Me], [ZA177;H,H,CFH.sub.2,H,Me], [ZA178;H,H,F,H,Me], [ZA179;H,H,Cl,H,Me], [ZA180;H,H,Br,H,Me], [ZA181;H,H,CN,H,Me], [ZA182;H,H,Ph,H,Me], [ZA183;H,H,OPh,H,Me], [ZA184;H,H,c-Pr,H,Me], [ZA185;H,H,c-Pen,H,Me], [ZA186;H,H,c-Hex,H,Me], [ZA187;H,H,H,H,OMe], [ZA188;Me,H,H,H,OMe], [ZA189;F,H,H,H,OMe], [ZA190;Cl,H,H,H,OMe], [ZA191;H,Me,H,H,OMe], [ZA192;H,Et,H,H,OMe], [ZA193;H,Pr,H,H,OMe], [ZA194;H,i-Pr,H,H,OMe], [ZA195;H,t-Bu,H,H,OMe], [ZA196;H,OMe,H,H,OMe], [ZA197;H,OEt,H,H,OMe], [ZA198;H,OPr,H,H,OMe], [ZA199;H,Oi-Pr,H,H,OMe], [ZA200;H,CF.sub.3,H,H,OMe]
[ZA201;H,CF.sub.2H,H,H,OMe], [ZA202;H,CFH.sub.2,H,H,OMe], [ZA203;H,F,H,H,OMe], [ZA204;H,Cl,H,H,OMe], [ZA205;H,Br,H,H,OMe], [ZA206;H,CN,H,H,OMe], [ZA207;H,Ph,H,H,OMe], [ZA208;H,OPh,H,H,OMe], [ZA209;H,c-Pr,H,H,OMe], [ZA210;H,c-Pen,H,H,OMe], [ZA211;H,c-Hex,H,H,OMe], [ZA212;H,H,Me,H,OMe], [ZA213;H,H,Et,H,OMe], [ZA214;H,H,Pr,H,OMe], [ZA215;H,H,i-Pr,H,OMe], [ZA216;H,H,t-Bu,H,OMe], [ZA217;H,H,OMe,H,OMe], [ZA218;H,H,OEt,H,OMe], [ZA219;H,H,OPr,H,OMe], [ZA220;H,H,Oi-Pr,H,OMe], [ZA221;H,H,CF.sub.3,H,OMe], [ZA222;H,H,CF.sub.2H,H,OMe], [ZA223;H,H,CFH.sub.2,H,OMe], [ZA224;H,H,F,H,OMe], [ZA225;H,H,Cl,H,OMe], [ZA226;H,H,Br,H,OMe], [ZA227;H,H,CN,H,OMe], [ZA228;H,H,Ph,H,OMe], [ZA229;H,H,OPh,H,OMe], [ZA230;H,H,c-Pr,H,OMe], [ZA231;H,H,c-Pen,H,OMe], [ZA232;H,H,c-Hex,H,OMe], [ZA233;H,H,H,H,CF.sub.3], [ZA234;Me,H,H,H,CF.sub.3], [ZA235;F,H,H,H,CF.sub.3], [ZA236;Cl,H,H,H,CF.sub.3], [ZA237;H,Me,H,H,CF.sub.3], [ZA238;H,Et,H,H,CF.sub.3], [ZA239;H,Pr,H,H,CF.sub.3], [ZA240;H,i-Pr,H,H,CF.sub.3], [ZA241;H,t-Bu,H,H,CF.sub.3], [ZA242;H,OMe,H,H,CF.sub.3], [ZA243;H,OEt,H,H,CF.sub.3], [ZA244;H,OPr,H,H,CF.sub.3], [ZA245;H,Oi-Pr,H,H,CF.sub.3], [ZA246;H,CF.sub.3,H,H,CF.sub.3], [ZA247;H,CF.sub.2H,H,H,CF.sub.3], [ZA248;H,CFH.sub.2,H,H,CF.sub.3], [ZA249;H,F,H,H,CF.sub.3], [ZA250;H,Cl,H,H,CF.sub.3], [ZA251;H,Br,H,H,CF.sub.3], [ZA252;H,CN,H,H,CF.sub.3], [ZA253;H,Ph,H,H,CF.sub.3], [ZA254;H,OPh,H,H,CF.sub.3], [ZA255;H,c-Pr,H,H,CF.sub.3], [ZA256;H,c-Pen,H,H,CF.sub.3], [ZA257;H,c-Hex,H,H,CF.sub.3], [ZA258;H,H,Me,H,CF.sub.3], [ZA259;H,H,Et,H,CF.sub.3], [ZA260;H,H,Pr,H,CF.sub.3], [ZA261;H,H,i-Pr,H,CF.sub.3], [ZA262;H,H,t-Bu,H,CF.sub.3], [ZA263;H,H,OMe,H,CF.sub.3], [ZA264;H,H,OEt,H,CF.sub.3], [ZA265;H,H,OPr,H,CF.sub.3], [ZA266;H,H,Oi-Pr,H,CF.sub.3], [ZA267;H,H,CF.sub.3,H,CF.sub.3], [ZA268;H,H,CF.sub.2H,H,CF.sub.3], [ZA269;H,H,CFH.sub.2,H,CF.sub.3], [ZA270;H,H,F,H,CF.sub.3], [ZA271;H,H,Cl,H,CF.sub.3], [ZA272;H,H,Br,H,CF.sub.3], [ZA273;H,H,CN,H,CF.sub.3], [ZA274;H,H,Ph,H,CF.sub.3], [ZA275;H,H,OPh,H,CF.sub.3], [ZA276;H,H,c-Pr,H,CF.sub.3], [ZA277;H,H,c-Pen,H,CF.sub.3], [ZA278;H,H,c-Hex,H,CF.sub.3], [ZA279;H,F,F,H,H], [ZA280;H,F,H,F,H], [ZA281;H,F,F,F,H], [ZA282; F. F,F,H,H], [ZA283; F. F,H,F,H], [ZA284; F,H,F,H,F], [ZA285;F,F,F,F,F], [ZA286;H,Cl,H,Cl,H], [ZA287;H,OMe,H,OMe,H], [ZA288;H,F,Cl,H,H], [ZA289;H,F,Me,H,H], [ZA290;H,F,OMe,H,H], [ZA291;H,F,CF.sub.3,H,H], [ZA292;H,Cl,F,H,H], [ZA293;H,Cl,Cl,H,H], [ZA294;H,Cl,Me,H,H], [ZA295;H,Cl,OMe,H,H], [ZA296;H,Cl,CF.sub.3,H,H], [ZA297;H,Me,F,H,H], [ZA298;H,Me,Cl,H,H], [ZA299;H,Me,Me,H,H], [ZA300;H,Me,OMe,H,H],
[ZA301;H,Me,CF.sub.3,H,H], [ZA302;H,OMe,F,H,H], [ZA303;H,OMe,Cl,H,H], [ZA304;H,OMe,Me,H,H], [ZA305;H,OMe,OMe,H,H], [ZA306;H,OMe,CF.sub.3,H,H], [ZA307;H,CF.sub.3,F,H,H], [ZA308;H,CF.sub.3,Cl,H,H], [ZA309;H,CF.sub.3,F,H,H], [ZA310;H,CF.sub.3,Cl,H,H], [ZA311;H,CF.sub.3,F,H,H]

[0504] The compound represented by formula (1B) wherein R.sup.1 represents a chlorine atom, L represents an oxygen atom, m is 1, and a combination of R.sup.X2, R.sup.X3, R.sup.X4, R.sup.X5 and R.sup.X6 represents any combinations described in the Combination A (hereinafter, referred to as Compound Class SX6).

[0505] The compound represented by formula (1B) wherein R.sup.1 represents a methyl group, L represents CH.sub.2, m is 1, and a combination of R.sup.X2, R.sup.X3, R.sup.X4, R.sup.X5 and R.sup.X6 represents any combinations described in the Combination A (hereinafter, referred to as Compound Class SX7).

[0506] The compound represented by formula (1B) wherein R.sup.1 represents a chlorine atom, L represents CH.sub.2, m is 1, and a combination of R.sup.X2, R.sup.X3, R.sup.X4, R.sup.X5 and R.sup.X6 represents any combinations described in the Combination A (hereinafter, referred to as Compound Class SX8).

[0507] The compound represented by formula (1B) wherein R.sup.1 represents a methyl group, L represents an oxygen atom, m is 2, and a combination of R.sup.X2, R.sup.X3, R.sup.X4, R.sup.X5, and R.sup.X6 represents any combinations descried in the Combination A (hereinafter, referred to as Compound Class SX9).

[0508] The compound represented by formula (1B) wherein R.sup.1 represents a chlorine atom, L represents an oxygen atom, m is 2, and a combination of R.sup.X2, R.sup.X3, R.sup.X4, R.sup.X5 and R.sup.X6 represents any combinations descried in the Combination A (hereinafter, referred to as Compound Class SX10).

[0509] The compound represented by formula (1B) wherein R.sup.1 represents a methyl group, L represents CH.sub.2, m is 2, and a combination of R.sup.X2, R.sup.X3, R.sup.X4, R.sup.X5 and R.sup.X6 represents any combinations descried in the Combination A (hereinafter, referred to as Compound Class SX11).

[0510] The compound represented by formula (1B) wherein R.sup.1 represents a chlorine atom, L represents CH.sub.2, m is 2, and a combination of R.sup.X2, R.sup.X3, R.sup.X4, R.sup.X5 and R.sup.X6 represents any combinations descried in the Combination A (hereinafter, referred to as Compound Class SX12).

[0511] The compound represented by formula (1B) wherein R.sup.1 represents a methyl group, L represents an oxygen atom, m is 3, and a combination of R.sup.X2, R.sup.X3, R.sup.X4, R.sup.X5 and R.sup.X6 represents any combinations descried in the Combination A (hereinafter, referred to as Compound Class SX13).

[0512] The compound represented by formula (1B) wherein R.sup.1 represents a chlorine atom, L represents an oxygen atom, m is 3, and a combination of R.sup.X2, R.sup.X3, R.sup.X4, R.sup.X5 and R.sup.X6 represents any combinations descried in the Combination A (hereinafter, referred to as Compound Class SX14).

[0513] The compound represented by formula (1B) wherein R.sup.1 represents a methyl group, L represents CH.sub.2, m is 3, and a combination of R.sup.X2, R.sup.X3, R.sup.X4, R.sup.X5 and R.sup.X6 represents any combinations descried in the Combination A (hereinafter, referred to as Compound Class SX15).

[0514] The compound represented by formula (1B) wherein R.sup.1 represents a chlorine atom, L represents CH.sub.2, m is 3, and a combination of R.sup.X2. R.sup.X3, R.sup.X4, R.sup.X5 and R.sup.X6 represents any combinations descried in the Combination A (hereinafter, referred to as Compound Class SX16).

[0515] A compound represented by formula (1C):

##STR00133##

[wherein

[0516] G represents any one of the following formulae G1 to G28:

##STR00134##

##STR00135##

[0517] R.sup.1 represents a methyl group, L represents an oxygen atom, m is 1, and a combination of a structure of G and the substituents of R.sup.X7, R.sup.X8, R.sup.X9, and R.sup.X10 which depend on the structure of G represent any combinations described in the Combination B (hereinafter, referred to as Compound Class SX17).

[0518] The Combination B consists of Substituent Nos. ZB1 to ZB1145. The Substituent Nos. ZB1 to ZB1145 represents a combination of a structure of G and the substituents of R.sup.X7, R.sup.X8, R.sup.X9, and R.sup.X10 which depend on the structure of G in the compound represented by formula (1C), the compound represented by formula (2C), and the compound represented by formula (3C), which are described below as [Substituent No.: G, R.sup.X7, R.sup.X8, R.sup.X9, R.sup.X10]. For example, Substituent No. ZB2 represents a combination wherein G represents G1, R.sup.X7 represents a methyl group, and a combination of R.sup.X8, R.sup.X9, and R.sup.X10 represents a hydrogen atom.

Combination B

[0519] [ZB1;G1,H,H,H,H], [ZB2;G1,Me,H,H,H], [ZB3;G1,Et,H,H,H], [ZB4;G1,Pr,H,H,H], [ZB5;G1,i-Pr,H,H,H], [ZB6;G1,c-Pr,H,H,H], [ZB7;G1,Ph,H,H,H], [ZB8;G1,OMe,H,H,H], [ZB9;G1,OEt,H,H,H], [ZB10;G1,OPh,H,H,H], [ZB11;G1,CF.sub.3,H,H,H], [ZB12;G1,F,H,H,H], [ZB13;G1,Cl,H,H,H], [ZB14;G1,Br,H,H,H], [ZB15;G1,CN,H,H,H], [ZB16;G1,H,Me,H,H], [ZB17;G1,H,Et,H,H], [ZB18;G1,H,Pr,H,H], [ZB19;G1,H,i-Pr,H,H], [ZB20;G1,H,c-Pr,H,H], [ZB21;G1,H,Ph,H,H], [ZB22;G1,H,OMe,H,H], [ZB23;G1,H,OEt,H,H], [ZB24;G1,H,OPh,H,H], [ZB25;G1,H,CF.sub.3,H,H], [ZB26;G1,H,F,H,H], [ZB27;G1,H,Cl,H,H], [ZB28;G1,H,Br,H,H], [ZB29;G1,H,CN,H,H], [ZB30;G1,H,H,Me,H], [ZB31;G1,H,H,Et,H], [ZB32;G1,H,H,Pr,H], [ZB33;G1,H,H,i-Pr,H], [ZB34;G1,H,H,c-Pr,H], [ZB35;G1,H,H,Ph,H], [ZB36;G1,H,H,OMe,H], [ZB37;G1,H,H,OEt,H], [ZB38;G1,H,H,OPh,H], [ZB39;G1,H,H,CF.sub.3,H], [ZB40;G1,H,H,F,H], [ZB41;G1,H,H,Cl,H], [ZB42;G1,H,H,Br,H], [ZB43;G1,H,H,CN,H], [ZB44;G1,H,H,H,Me], [ZB45;G1,H,H,H,Et], [ZB46;G1,H,H,H,Pr], [ZB47;G1,H,H,H,i-Pr], [ZB48;G1,H,H,H,c-Pr], [ZB49;G1,H,H,H,Ph], [ZB50;G1,H,H,H,OMe], [ZB51;G1,H,H,H,OEt], [ZB52;G1,H,H,H,OPh], [ZB53;G1,H,H,H,CF.sub.3], [ZB54;G1,H,H,H,F], [ZB55;G1,H,H,H,C1], [ZB56;G1,H,H,H,Br], [ZB57;G1,H,H,H,CN], [ZB58;G2,H,H,H,H], [ZB59;G2,Me,H,H,H], [ZB60;G2,Et,H,H,H], [ZB61;G2,Pr,H,H,H], [ZB62;G2,i-Pr,H,H,H], [ZB63;G2,c-Pr,H,H,H], [ZB64;G2,Ph,H,H,H], [ZB65;G2,OMe,H,H,H], [ZB66;G2,OEt,H,H,H], [ZB67;G2,OPh,H,H,H], [ZB68;G2,CF.sub.3,H,H,H], [ZB69;G2,F,H,H,H], [ZB70;G2,Cl,H,H,H], [ZB71;G2,Br,H,H,H], [ZB72;G2,CN,H,H,H], [ZB73;G2,H,Me,H,H], [ZB74;G2,H,Et,H,H], [ZB75;G2,H,Pr,H,H], [ZB76;G2,H,i-Pr,H,H], [ZB77;G2,H,c-Pr,H,H], [ZB78;G2,H,Ph,H,H], [ZB79;G2,H,OMe,H,H], [ZB80;G2,H,OEt,H,H], [ZB81;G2,H,OPh,H,H], [ZB82;G2,H,CF.sub.3,H,H], [ZB83;G2,H,F,H,H], [ZB84;G2,H,Cl,H,H], [ZB85;G2,H,Br,H,H], [ZB86;G2,H,CN,H,H], [ZB87;G2,H,H,Me,H], [ZB88;G2,H,H,Et,H], [ZB89;G2,H,H,Pr,H], [ZB90;G2,H,H,i-Pr,H], [ZB91;G2,H,H,c-Pr,H], [ZB92;G2,H,H,Ph,H], [ZB93;G2,H,H,OMe,H], [ZB94;G2,H,H,OEt,H], [ZB95;G2,H,H,OPh,H], [ZB96;G2,H,H,CF.sub.3,H], [ZB97;G2,H,H,F,H], [ZB98;G2,H,H,Cl,H], [ZB99;G2,H,H,Br,H], [ZB100;G2,H,H,CN,H]
[ZB101;G2,H,H,H,Me], [ZB102;G2,H,H,H,Et], [ZB103;G2,H,H,H,Pr], [ZB104;G2,H,H,H,i-Pr], [ZB105;G2,H,H,H,c-Pr], [ZB106;G2,H,H,H,Ph], [ZB107;G2,H,H,H,OMe], [ZB108;G2,H,H,H,OEt], [ZB109;G2,H,H,H,OPh], [ZB110;G2,H,H,H,CF.sub.3], [ZB111;G2,H,H,H,F], [ZB112;G2,H,H,H,C1], [ZB113;G2,H,H,H,Br], [ZB114;G2,H,H,H,CN], [ZB115;G3,H,H,H,H], [ZB116;G3,Me,H,H,H], [ZB117;G3,Et,H,H,H], [ZB118;G3,Pr,H,H,H], [ZB119;G3,i-Pr,H,H,H], [ZB120;G3,c-Pr,H,H,H], [ZB121;G3,Ph,H,H,H], [ZB122;G3,OMe,H,H,H], [ZB123;G3,OEt,H,H,H], [ZB124;G3,OPh,H,H,H], [ZB125;G3,CF.sub.3,H,H,H], [ZB126;G3,F,H,H,H], [ZB127;G3,Cl,H,H,H], [ZB128;G3,Br,H,H,H], [ZB129;G3,CN,H,H,H], [ZB130;G3,H,Me,H,H], [ZB131;G3,H,Et,H,H], [ZB132;G3,H,Pr,H,H], [ZB133;G3,H,i-Pr,H,H], [ZB134;G3,H,c-Pr,H,H], [ZB135;G3,H,Ph,H,H], [ZB136;G3,H,OMe,H,H], [ZB137;G3,H,OEt,H,H], [ZB138;G3,H,OPh,H,H], [ZB139;G3,H,CF.sub.3,H,H], [ZB140;G3,H,F,H,H], [ZB141;G3,H,Cl,H,H], [ZB142;G3,H,Br,H,H], [ZB143; G3,H,CN,H,H], [ZB144;G3,H,H,Me,H], [ZB145;G3,H,H,Et,H], [ZB146;G3,H,H,Pr,H], [ZB147;G3,H,H,i-Pr,H], [ZB148;G3,H,H,c-Pr,H], [ZB149;G3,H,H,Ph,H], [ZB150;G3,H,H,OMe,H], [ZB151;G3,H,H,OEt,H], [ZB152;G3,H,H,OPh,H], [ZB153;G3,H,H,CF.sub.3,H], [ZB154;G3,H,H,F,H], [ZB155;G3,H,H,Cl,H], [ZB156;G3,H,H,Br,H], [ZB157;G3,H,H,CN,H], [ZB158;G3,H,H,H,Me], [ZB159;G3,H,H,H,Et], [ZB160;G3,H,H,H,Pr], [ZB161;G3,H,H,H,i-Pr], [ZB162;G3,H,H,H,c-Pr], [ZB163;G3,H,H,H,Ph], [ZB164;G3,H,H,H,OMe], [ZB165;G3,H,H,H,OEt], [ZB166;G3,H,H,H,OPh], [ZB167;G3,H,H,H,CF.sub.3], [ZB168;G3,H,H,H,F], [ZB169;G3,H,H,H,C1], [ZB170;G3,H,H,H,Br], [ZB171;G3,H,H,H,CN], [ZB172;G4,H,H,H,-], [ZB173;G4,Me,H,H,-], [ZB174;G4,Et,H,H,-], [ZB175;G4,Pr,H,H,-], [ZB176;G4,i-Pr,H,H,-], [ZB177;G4,c-Pr,H,H,-], [ZB178;G4,Ph,H,H,-], [ZB179;G4,OMe,H,H,-], [ZB180;G4,OEt,H,H,-], [ZB181;G4,OPh,H,H,-], [ZB182;G4,CF.sub.3,H,H,-], [ZB183;G4,F,H,H,-], [ZB184;G4,Cl,H,H,-], [ZB185;G4,Br,H,H,-], [ZB186;G4,CN,H,H,-], [ZB187;G4,H,Me,H,-], [ZB188;G4,H,Et,H,-], [ZB189;G4,H,Pr,H,-], [ZB190;G4,H,i-Pr,H,-], [ZB191;G4,H,c-Pr,H,-], [ZB192;G4,H,Ph,H,-], [ZB193;G4,H,OMe,H,-], [ZB194;G4,H,OEt,H,-], [ZB195;G4,H,OPh,H,-], [ZB196;G4,H,CF.sub.3,H,-], [ZB197;G4,H,F,H,-], [ZB198;G4,H,Cl,H,-], [ZB199;G4,H,Br,H,-], [ZB200;G4,H,CN,H,-]
[ZB201;G4,H,H,Me,-], [ZB202;G4,H,H,Et,-], [ZB203;G4,H,H,Pr,-], [ZB204;G4,H,H,i-Pr,-], [ZB205;G4,H,H,c-Pr,-], [ZB206;G4,H,H,Ph,-], [ZB207;G4,H,H,OMe,-], [ZB208;G4,H,H,OEt,-], [ZB209;G4,H,H,OPh,-], [ZB210;G4,H,H,CF.sub.3,-], [ZB211;G4,H,H,F,-], [ZB212;G4,H,H,Cl,-], [ZB213;G4,H,H,Br,-], [ZB214;G4,H,H,CN,-], [ZB215;G5,H,H,H,-], [ZB216;G5,Me,H,H,-], [ZB217;G5,Et,H,H,-], [ZB218;G5,Pr,H,H,-], [ZB219;G5,i-Pr,H,H,-], [ZB220;G5,c-Pr,H,H,-], [ZB221;G5,Ph,H,H,-], [ZB222;G5,OMe,H,H,-], [ZB223;G5,OEt,H,H,-], [ZB224;G5,OPh,H,H,-], [ZB225;G5,CF.sub.3,H,H,-], [ZB226;G5,F,H,H,-], [ZB227;G5,Cl,H,H,-], [ZB228;G5,Br,H,H,-], [ZB229;G5,CN,H,H,-], [ZB230;G5,H,Me,H,-], [ZB231;G5,H,Et,H,-], [ZB232;G5,H,Pr,H,-], [ZB233;G5,H,i-Pr,H,-], [ZB234;G5,H,c-Pr,H,-], [ZB235;G5,H,Ph,H,-], [ZB236;G5,H,OMe,H,-], [ZB237;G5,H,OEt,H,-], [ZB238;G5,H,OPh,H,-], [ZB239;G5,H,CF.sub.3,H,-], [ZB240;G5,H,F,H,-], [ZB241;G5,H,Cl,H,-], [ZB242;G5,H,Br,H,-], [ZB243;G5,H,CN,H,-], [ZB244;G5,H,H,Me,-], [ZB245;G5,H,H,Et,-], [ZB246;G5,H,H,Pr,-], [ZB247;G5,H,H,i-Pr,-], [ZB248;G5,H,H,c-Pr,-], [ZB249;G5,H,H,Ph,-], [ZB250;G5,H,H,OMe,-], [ZB251;G5,H,H,OEt,-], [ZB252;G5,H,H,OPh,-], [ZB253;G5,H,H,CF.sub.3,-], [ZB254;G5,H,H,F,-], [ZB255;G5,H,H,Cl,-], [ZB256;G5,H,H,Br,-], [ZB257;G5,H,H,CN,-], [ZB258;G6,H,H,H,-], [ZB259;G6,Me,H,H,-], [ZB260;G6,Et,H,H,-], [ZB261;G6,Pr,H,H,-], [ZB262;G6,i-Pr,H,H,-], [ZB263;G6,c-Pr,H,H,-], [ZB264;G6,Ph,H,H,-], [ZB265;G6,OMe,H,H,-], [ZB266;G6,OEt,H,H,-], [ZB267;G6,OPh,H,H,-], [ZB268;G6,CF.sub.3,H,H,-], [ZB269;G6,F,H,H,-], [ZB270;G6,Cl,H,H,-], [ZB271;G6,Br,H,H,-], [ZB272;G6,CN,H,H,-], [ZB273;G6,H,Me,H,-], [ZB274;G6,H,Et,H,-], [ZB275;G6,H,Pr,H,-], [ZB276;G6,H,i-Pr,H,-], [ZB277;G6,H,c-Pr,H,-], [ZB278;G6,H,Ph,H,-], [ZB279;G6,H,OMe,H,-], [ZB280;G6,H,OEt,H,-], [ZB281;G6,H,OPh,H,-], [ZB282;G6,H,CF.sub.3,H,-], [ZB283;G6,H,F,H,-], [ZB284;G6,H,Cl,H,-], [ZB285;G6,H,Br,H,-], [ZB286;G6,H,CN,H,-], [ZB287;G6,H,H,Me,-], [ZB288;G6,H,H,Et,-], [ZB289;G6,H,H,Pr,-], [ZB290;G6,H,H,i-Pr,-], [ZB291;G6,H,H,c-Pr,-], [ZB292;G6,H,H,Ph,-], [ZB293;G6,H,H,OMe,-], [ZB294;G6,H,H,OEt,-], [ZB295;G6,H,H,OPh,-], [ZB296;G6,H,H,CF.sub.3,-], [ZB297;G6,H,H,F,-], [ZB298;G6,H,H,Cl,-], [ZB299;G6,H,H,Br,-], [ZB300;G6,H,H,CN,-]
[ZB301;G7,H,H,H,-], [ZB302;G7,Me,H,H,-], [ZB303;G7,Et,H,H,-], [ZB304;G7,Pr,H,H,-], [ZB305;G7,i-Pr,H,H,-], [ZB306;G7,c-Pr,H,H,-], [ZB307;G7,Ph,H,H,-], [ZB308;G7,OMe,H,H,-], [ZB309;G7,OEt,H,H,-], [ZB310;G7,OPh,H,H,-], [ZB311;G7,CF.sub.3,H,H,-], [ZB312;G7,F,H,H,-], [ZB313;G7,Cl,H,H,-], [ZB314;G7,Br,H,H,-], [ZB315;G7,CN,H,H,-], [ZB316;G7,H,Me,H,-], [ZB317;G7,H,Et,H,-], [ZB318;G7,H,Pr,H,-], [ZB319;G7,H,i-Pr,H,-], [ZB320;G7,H,c-Pr,H,-], [ZB321;G7,H,Ph,H,-], [ZB322;G7,H,OMe,H,-], [ZB323;G7,H,OEt,H,-], [ZB324;G7,H,OPh,H,-], [ZB325;G7,H,CF.sub.3,H,-], [ZB326;G7,H,F,H,-], [ZB327;G7,H,Cl,H,-], [ZB328;G7,H,Br,H,-], [ZB329;G7,H,CN,H,-], [ZB330;G7,H,H,Me,-], [ZB331;G7,H,H,Et,-], [ZB332;G7,H,H,Pr,-], [ZB333;G7,H,H,i-Pr,-], [ZB334;G7,H,H,c-Pr,-], [ZB335;G7,H,H,Ph,-], [ZB336;G7,H,H,OMe,-], [ZB337;G7,H,H,OEt,-], [ZB338;G7,H,H,OPh,-], [ZB339;G7,H,H,CF.sub.3,-], [ZB340;G7,H,H,F,-], [ZB341;G7,H,H,Cl,-], [ZB342;G7,H,H,Br,-], [ZB343;G7,H,H,CN,-], [ZB344;G8,H,H,H,-], [ZB345;G8,Me,H,H,-], [ZB346;G8,Et,H,H,-], [ZB347;G8,Pr,H,H,-], [ZB348;G8,i-Pr,H,H,-], [ZB349;G8,c-Pr,H,H,-], [ZB350;G8,Ph,H,H,-], [ZB351;G8,OMe,H,H,-], [ZB352;G8,OEt,H,H,-], [ZB353;G8,OPh,H,H,-], [ZB354;G8,CF.sub.3,H,H,-], [ZB355;G8,F,H,H,-], [ZB356;G8,Cl,H,H,-], [ZB357;G8,Br,H,H,-], [ZB358;G8,CN,H,H,-], [ZB359;G8,H,Me,H,-], [ZB360;G8,H,Et,H,-], [ZB361;G8,H,Pr,H,-], [ZB362;G8,H,i-Pr,H,-], [ZB363;G8,H,c-Pr,H,-], [ZB364;G8,H,Ph,H,-], [ZB365;G8,H,OMe,H,-], [ZB366;G8,H,OEt,H,-], [ZB367;G8,H,OPh,H,-], [ZB368;G8,H,CF.sub.3,H,-], [ZB369;G8,H,F,H,-], [ZB370;G8,H,Cl,H,-], [ZB371;G8,H,Br,H,-], [ZB372;G8,H,CN,H,-], [ZB373;G8,H,H,Me,-], [ZB374;G8,H,H,Et,-], [ZB375;G8,H,H,Pr,-], [ZB376;G8,H,H,i-Pr,-], [ZB377;G8,H,H,c-Pr,-], [ZB378;G8,H,H,Ph,-], [ZB379;G8,H,H,OMe,-], [ZB380;G8,H,H,OEt,-], [ZB381;G8,H,H,OPh,-], [ZB382;G8,H,H,CF.sub.3,-], [ZB383;G8,H,H,F,-], [ZB384;G8,H,H,Cl,-], [ZB385;G8,H,H,Br,-], [ZB386;G8,H,H,CN,-], [ZB387;G9,H,H,H,-], [ZB388;G9,Me,H,H,-], [ZB389;G9,Et,H,H,-], [ZB390;G9,Pr,H,H,-], [ZB391;G9,i-Pr,H, H,-], [ZB392;G9, c-Pr,H,H,-], [ZB393;G9,Ph,H,H,-], [ZB394;G9,OMe,H,H,-], [ZB395;G9,OEt,H,H,-], [ZB396;G9,OPh,H,H,-], [ZB397;G9,CF.sub.3,H,H,-], [ZB398;G9,F,H,H,-], [ZB399;G9,Cl,H,H,-], [ZB400;G9,Br,H,H,-]
[ZB401;G9,CN,H,H,-], [ZB402;G9,H,Me,H,-], [ZB403;G9,H,Et,H,-], [ZB404;G9,H,Pr,H.-1, [ZB405;G9,H,i-Pr,H,-], [ZB406;G9,H,c-Pr,H,-], [ZB407;G9,H,Ph,H,-], [ZB408;G9,H,OMe,H,-], [ZB409;G9,H,OEt,H,-], [ZB410;G9,H,OPh,H,-], [ZB411;G9,H,CF.sub.3,H,-], [ZB412;G9,H,F,H,-], [ZB413;G9,H,Cl,H,-], [ZB414;G9,H,Br,H,-], [ZB415;G9,H,CN,H,-], [ZB416;G9,H,H,Me,-], [ZB417;G9,H,H,Et,-], [ZB418;G9,H,H,Pr,-], [ZB419;G9,H,H,i-Pr,-], [ZB420;G9,H,H,c-Pr,-], [ZB421;G9,H,H,Ph,-], [ZB422;G9,H,H,OMe,-], [ZB423;G9,H,H,OEt,-], [ZB424;G9,H,H,OPh,-], [ZB425;G9,H,H,CF.sub.3,-], [ZB426;G9,H,H,F,-], [ZB427;G9,H,H,Cl,-], [ZB428;G9,H,H,Br,-], [ZB429;G9,H,H,CN,-], [ZB430;G10,H,H,H,-], [ZB431;G10,Me,H,H,-], [ZB432;G10,Et,H,H,-], [ZB433;G10,Pr,H,H,-], [ZB434;G10,i-Pr,H,H,-], [ZB435;G10,c-Pr,H,H,-], [ZB436;G10,Ph,H,H,-], [ZB437;G10,OMe,H,H,-], [ZB438;G10,OEt,H,H,-], [ZB439;G10,OPh,H,H,-], [ZB440;G10,CF.sub.3,H,H,-], [ZB441;G10,F,H,H,-], [ZB442;G10,Cl,H,H,-], [ZB443;G10,Br,H,H,-], [ZB444;G10,CN,H,H,-], [ZB445;G10,H,Me,H,-], [ZB446;G10,H,Et,H,-], [ZB447;G10,H,Pr,H,-], [ZB448;G10,H,i-Pr,H,-], [ZB449;G10,H,c-Pr,H,-], [ZB450;G10,H,Ph,H,-], [ZB451;G10,H,OMe,H,-], [ZB452;G10,H,OEt,H,-], [ZB453;G10,H,OPh,H,-], [ZB454;G10,H,CF.sub.3,H,-], [ZB455;G10,H,F,H,-], [ZB456;G10,H,Cl,H,-], [ZB457;G10,H,Br,H,-], [ZB458;G10,H,CN,H,-], [ZB459;G10,H,H,Me,-], [ZB460;G10,H,H,Et,-], [ZB461;G10,H,H,Pr,-], [ZB462;G10,H,H,i-Pr,-], [ZB463;G10,H,H,c-Pr,-], [ZB464;G10,H,H,Ph,-], [ZB465;G10,H,H,OMe,-], [ZB466;G10,H,H,OEt,-], [ZB467;G10,H,H,OPh,-], [ZB468;G10,H,H,CF.sub.3,-], [ZB469;G10,H,H,F,-], [ZB470;G10,H,H,Cl,-], [ZB471;G10,H,H,Br,-], [ZB472;G10,H,H,CN,-], [ZB473;G11,H,H,H,-], [ZB474;G11,H,Me,H,-], [ZB475;G11,HEt,H,-], [ZB476;G11,HPr,H,-], [ZB477;G11,Hi-Pr,H,-], [ZB478;G11,Hc-Pr,H,-], [ZB479;G11,HPh,H,-], [ZB480;G11,HOMe,H,-], [ZB481;G11,HOEt,H,-], [ZB482;G11,HOPh,H,-], [ZB483;G11,HCF.sub.3,H,-], [ZB484;G11,HF,H,-], [ZB485;G11,HCl,H,-], [ZB486;G11,HBr,H,-], [ZB487;G11,HCN,H,-], [ZB488;G11,H,H,Me,-], [ZB489;G11,H,H,Et,-], [ZB490;G11,H,H,Pr,-], [ZB491;G11,H,H,i-Pr,-], [ZB492;G11,H,H,c-Pr,-], [ZB493;G11,H,H,Ph,-], [ZB494;G11,H,H,OMe,-], [ZB495;G11,H,H,OEt,-], [ZB496;G11,H,H,OPh,-], [ZB497;G11,H,H,CF.sub.3,-], [ZB498;G11,H,H,F,-], [ZB499;G11,H,H,Cl,-], [ZB500;G11,H,H,Br,-]
[ZB501;G11,H,H,CN,-], [ZB502;G11,Me,H,H,-], [ZB503;G11,Me,Me,H,-], [ZB504;G11,MeEt,H,-], [ZB505;G11,MePr,H,-], [ZB506;G11,Mei-Pr,H,-], [ZB507;G11,Mec-Pr,H,-], [ZB508;G11,MePh,H,-], [ZB509;G11,MeOMe,H,-], [ZB510;G11,MeOEt,H,-], [ZB511;G11,MeOPh,H,-], [ZB512;G11,MeCF.sub.3,H,-], [ZB513;G11,MeF,H,-], [ZB514;G11,MeCl,H,-], [ZB515;G11,MeBr,H,-], [ZB516;G11,MeCN,H,-], [ZB517;G11,Me,H,Me,-], [ZB518;G11,Me,H,Et,-], [ZB519;G11,Me,H,Pr,-], [ZB520;G11,Me,H,i-Pr,-], [ZB521;G11,Me,H,c-Pr,-], [ZB522;G11,Me,H,Ph,-], [ZB523;G11,Me,H,OMe,-], [ZB524;G11,Me,H,OEt,-], [ZB525;G11,Me,H,OPh,-], [ZB526;G11,Me,H,CF.sub.3,-], [ZB527;G11,Me,H,F,-], [ZB528;G11,Me,H,Cl,-], [ZB529;G11,Me,H,Br,-], [ZB530;G11,Me,H,CN,-], [ZB531;G12,H,H,H,-], [ZB532;G12,Me,H,H,-], [ZB533;G12,Et,H,H,-], [ZB534;G12,Pr,H,H,-], [ZB535;G12,i-Pr,H,H,-], [ZB536;G12,c-Pr,H,H,-], [ZB537;G12,Ph,H,H,-], [ZB538;G12,OMe,H,H,-], [ZB539;G12,OEt,H,H,-], [ZB540;G12,OPh,H,H,-], [ZB541;G12,CF.sub.3,H,H,-], [ZB542;G12,F,H,H,-], [ZB543;G12,Cl,H,H,-], [ZB544;G12,Br,H,H,-], [ZB545;G12,CN,H,H,-], [ZB546;G12,H,Me,H,-], [ZB547;G12,H,Et,H,-], [ZB548;G12,H,Pr,H,-], [ZB549;G12,H,i-Pr,H,-], [ZB550;G12,H,c-Pr,H,-], [ZB551;G12,H,Ph,H,-], [ZB552;G12,H,OMe,H,-], [ZB553;G12,H,OEt,H,-], [ZB554;G12,H,OPh,H,-], [ZB555;G12,H,CF.sub.3,H,-], [ZB556;G12,H,F,H,-], [ZB557;G12,H,Cl,H,-], [ZB558;G12,H,Br,H,-], [ZB559;G12,H,CN,H,-], [ZB560;G12,H,H,Me,-], [ZB561;G12,H,H,Et,-], [ZB562;G12,H,H,Pr,-], [ZB563;G12,H,H,i-Pr,-], [ZB564;G12,H,H,c-Pr,-], [ZB565;G12,H,H,Ph,-], [ZB566;G12,H,H,OMe,-], [ZB567;G12,H,H,OEt,-], [ZB568;G12,H,H,OPh,-], [ZB569;G12,H,H,CF.sub.3,-], [ZB570;G12,H,H,F,-], [ZB571;G12,H,H,Cl,-], [ZB572;G12,H,H,Br,-], [ZB573;G12,H,H,CN,-], [ZB574;G13,H,H,H,-], [ZB575;G13,Me,H,H,-], [ZB576;G13,Et,H,H,-], [ZB577;G13,Pr,H,H,-], [ZB578;G13,i-Pr,H,H,-], [ZB579;G13,c-Pr,H,H,-], [ZB580;G13,Ph,H,H,-], [ZB581;G13,OMe,H,H,-], [ZB582;G13,OEt,H,H,-], [ZB583;G13,OPh,H,H,-], [ZB584;G13,CF.sub.3,H,H,-], [ZB585;G13,F,H,H,-], [ZB586;G13,Cl,H,H,-], [ZB587;G13,Br,H,H,-], [ZB588;G13,CN,H,H,-], [ZB589;G13,H,H,Me,-], [ZB590;G13,H,H,Et,-], [ZB591;G13,H,H,Pr,-], [ZB592;G13,H,H,i-Pr,-], [ZB593;G13,H,H,c-Pr,-], [ZB594;G13,H,H,Ph,-], [ZB595;G13,H,H,OMe,-], [ZB596;G13,H,H,OEt,-], [ZB597;G13,H,H,OPh,-], [ZB598;G13,H,H,CF.sub.3,-], [ZB599;G13,H,H,F,-], [ZB600;G13,H,H,Cl,-]
[ZB601;G13,H,H,Br,-], [ZB602;G13,H,H,CN,-], [ZB603;G13,H,Me,H,-], [ZB604;G13,Me,Me,H,-], [ZB605;G13,Et,Me,H,-], [ZB606;G13,Pr,Me,H,-], [ZB607;G13,i-Pr,Me, H,-], [ZB608;G13, c-Pr,Me, H,-], [ZB609;G13, Ph,Me,H,-], [ZB610;G13,OMe,Me,H,-], [ZB611;G13,OEt,Me,H,-], [ZB612;G13,OPh,Me,H,-], [ZB613;G13,CF.sub.3,Me,H,-], [ZB614;G13,F,Me,H,-], [ZB615;G13,Cl,Me,H,-], [ZB616;G13,Br,Me,H,-], [ZB617;G13,CN,Me,H,-], [ZB618;G13,H,Me,Me,-], [ZB619;G13,H,Me,Et,-], [ZB620;G13,H,Me,Pr,-], [ZB621;G13,H,Me,i-Pr,-], [ZB622;G13,H,Me,c-Pr,-], [ZB623;G13,H,Me,Ph,-], [ZB624;G13,H,Me,OMe,-], [ZB625;G13,H,Me,OEt,-], [ZB626;G13,H,Me,OPh,-], [ZB627;G13,H,Me,CF.sub.3,-], [ZB628;G13,H,Me,F,-], [ZB629;G13,H,Me,Cl,-], [ZB630;G13,H,Me,Br,-], [ZB631;G13,H,Me,CN,-], [ZB632;G14,H,H,H,-], [ZB633;G14,Me,H,H,-], [ZB634;G14,Et,H,H,-], [ZB635;G14,Pr,H,H,-], [ZB636;G14,i-Pr,H,H,-], [ZB637;G14,c-Pr,H,H,-], [ZB638;G14,Ph,H,H,-], [ZB639;G14,OMe,H,H,-], [ZB640;G14,OEt,H,H,-], [ZB641;G14,OPh,H,H,-], [ZB642;G14,CF.sub.3,H,H,-], [ZB643;G14, F,H,H,-], [ZB644;G14,Cl,H,H,-], [ZB645;G14,Br,H,H,-], [ZB646;G14,CN,H,H,-], [ZB647;G14,H,Me,H,-], [ZB648;G14,H,Et,H,-], [ZB649;G14,H,Pr,H,-], [ZB650;G14,H,i-Pr,H,-], [ZB651;G14,H,c-Pr,H,-], [ZB652;G14,H,Ph,H,-], [ZB653;G14,H,OMe,H,-], [ZB654;G14,H,OEt,H,-], [ZB655;G14,H,OPh,H,-], [ZB656;G14,H,CF.sub.3,H,-], [ZB657;G14,H,F,H,-], [ZB658;G14,H,Cl,H,-], [ZB659;G14,H,Br,H,-], [ZB660;G14,H,CN,H,-], [ZB661;G14,H,H,Me,-], [ZB662;G14,H,H,Et,-], [ZB663;G14,H,H,Pr,-], [ZB664;G14,H,H,i-Pr,-], [ZB665;G14,H,H,c-Pr,-], [ZB666;G14,H,H,Ph,-], [ZB667;G14,H,H,OMe,-], [ZB668;G14,H,H,OEt,-], [ZB669;G14,H,H,OPh,-], [ZB670;G14,H,H,CF.sub.3,-], [ZB671;G14,H,H,F,-], [ZB672;G14,H,H,Cl,-], [ZB673;G14,H,H,Br,-], [ZB674;G14,H,H,CN,-], [ZB675;G15,H,H,H,-], [ZB676;G15,Me,H,H,-], [ZB677;G15,Et,H,H,-], [ZB678;G15,Pr,H,H,-], [ZB679;G15,i-Pr,H,H,-], [ZB680;G15, c-Pr, H, H,-], [ZB681;G15, Ph, H, H,-], [ZB682;G15,OMe,H,H,-], [ZB683;G15,OEt,H,H,-], [ZB684;G15,OPh,H,H,-], [ZB685;G15,CF.sub.3,H,H,-], [ZB686;G15,F,H,H,-], [ZB687;G15,Cl,H,H,-], [ZB688;G15,Br,H,H,-], [ZB689;G15,CN,H,H,-], [ZB690;G15,H,Me,H,-], [ZB691;G15,H,Et,H,-], [ZB692;G15,H,Pr,H,-], [ZB693;G15,H,i-Pr,H,-], [ZB694;G15,H,c-Pr,H,-], [ZB695;G15,H,Ph,H,-], [ZB696;G15,H,OMe,H,-], [ZB697;G15,H,OEt,H,-], [ZB698;G15,H,OPh,H,-], [ZB699;G15,H,CF.sub.3,H,-], [ZB700;G15,H,F,H,-]
[ZB701;G15,H,Cl,H,-], [ZB702;G15,H,Br,H,-], [ZB703;G15,H,CN,H,-], [ZB704;G15,H,H,Me,-], [ZB705;G15,H,H,Et,-], [ZB706;G15,H,H,Pr,-], [ZB707;G15,H,H,i-Pr,-], [ZB708;G15,H,H,c-Pr,-], [ZB709;G15,H,H,Ph,-], [ZB710;G15,H,H,OMe,-], [ZB711;G15,H,H,OEt,-], [ZB712;G15,H,H,OPh,-], [ZB713;G15,H,H,CF.sub.3,-], [ZB714;G15,H,H,F,-], [ZB715;G15,H,H,Cl,-], [ZB716;G15,H,H,Br,-], [ZB717;G15,H,H,CN,-], [ZB718;G16,H,H,-,-], [ZB719;G16,Me,H,-,-], [ZB720;G16,Et,H,-,-], [ZB721;G16,Pr,H,-,-], [ZB722;G16,i-Pr,H,-,-], [ZB723;G16,c-Pr,H,-,-], [ZB724;G16,Ph,H,-,-], [ZB725;G16,OMe,H,-,-], [ZB726;G16,OEt,H,-,-], [ZB727;G16,OPh,H,-,-], [ZB728;G16,CF.sub.3,H,-,-], [ZB729;G16,F,H,-,-], [ZB730;G16,Cl,H,-,-], [ZB731;G16,Br,H,-,-], [ZB732;G16,CN,H,-,-], [ZB733;G16,H,Me,-,-], [ZB734;G16,H,Et,-,-], [ZB735;G16,H,Pr,-,-], [ZB736;G16,H,i-Pr,-,-], [ZB737;G16,H,c-Pr,-,-], [ZB738;G16,H,Ph,-,-], [ZB739;G16,H,OMe,-,-], [ZB740;G16,H,OEt,-,-], [ZB741;G16,H,OPh,-,-], [ZB742;G16,H,CF.sub.3,-,-], [ZB743;G16,H, F,-,-], [ZB744;G16,H,Cl,-,-], [ZB745;G16,H,Br,-,-], [ZB746;G16,H,CN,-,-], [ZB747;G17,H,H,-,-], [ZB748;G17,Me,H,-,-], [ZB749;G17,Et,H,-,-], [ZB750;G17,Pr,H,-,-], [ZB751;G17,i-Pr,H,-,-], [ZB752;G17,c-Pr,H,-,-], [ZB753;G17,Ph,H,-,-], [ZB754;G17,OMe,H,-,-], [ZB755;G17,OEt,H,-,-], [ZB756;G17,OPh,H,-,-], [ZB757;G17,CF.sub.3,H,-,-], [ZB758;G17,F,H,-,-], [ZB759;G17,Cl,H,-,-], [ZB760;G17,Br,H,-,-], [ZB761;G17,CN,H,-,-], [ZB762;G17,H,Me,-,-], [ZB763;G17,H,Et,-,-], [ZB764;G17,H,Pr,-,-], [ZB765;G17,H,i-Pr,-,-], [ZB766;G17,H,c-Pr,-,-], [ZB767;G17,H,Ph,-,-], [ZB768;G17,H,OMe,-,-], [ZB769;G17,H,OEt,-,-], [ZB770;G17,H,OPh,-,-], [ZB771;G17,H,CF.sub.3,-,-], [ZB772;G17,H,F,-,-], [ZB773;G17,H,Cl,-,-], [ZB774;G17,H,Br,-,-], [ZB775;G17,H,CN,-,-], [ZB776;G18,H,H,-,-], [ZB777;G18,Me,H,-,-], [ZB778;G18,Et,H,-,-], [ZB779;G18,Pr,H,-,-], [ZB780;G18,i-Pr,H,-,-], [ZB781;G18,c-Pr,H,-,-], [ZB782;G18,Ph,H,-,-], [ZB783;G18,OMe,H,-,-], [ZB784;G18,OEt,H,-,-], [ZB785;G18,OPh,H,-,-], [ZB786;G18,CF.sub.3,H,-,-], [ZB787;G18,F,H,-,-], [ZB788;G18,Cl,H,-,-], [ZB789;G18,Br,H,-,-], [ZB790;G18,CN,H,-,-], [ZB791;G18,H,Me,-,-], [ZB792;G18,H,Et,-,-], [ZB793;G18,H,Pr,-,-], [ZB794;G18,H,i-Pr,-,-], [ZB795;G18,H,c-Pr,-,-], [ZB796;G18,H,Ph,-,-], [ZB797;G18,H,OMe,-,-], [ZB798;G18,H,OEt,-,-], [ZB799;G18,H,OPh,-,-], [ZB800;G18,H,CF.sub.3,-,-]
[ZB801;G18,H,F,-,-], [ZB802;G18,H,Cl,-,-], [ZB803;G18,H,Br,-,-], [ZB804;G18,H,CN,-,-], [ZB805;G19,H,H,-,-], [ZB806;G19,Me,H,-,-], [ZB807;G19,Et,H,-,-], [ZB808;G19,Pr,H,-,-], [ZB809;G19,i-Pr,H,-,-], [ZB810;G19,c-Pr,H,-,-], [ZB811;G19,Ph,H,-,-], [ZB812;G19,OMe,H,-,-], [ZB813;G19,OEt,H,-,-], [ZB814;G19,OPh,H,-,-], [ZB815;G19,CF.sub.3,H,-,-], [ZB816;G19,F,H,-,-], [ZB817;G19,Cl,H,-,-], [ZB818;G19,Br,H,-,-], [ZB819;G19,CN,H,-,-], [ZB820;G19,H,Me,-,-], [ZB821;G19,H,Et,-,-], [ZB822;G19,H,Pr,-,-], [ZB823;G19,H,i-Pr,-,-], [ZB824;G19,H,c-Pr,-,-], [ZB825;G19,H,Ph,-,-], [ZB826;G19,H,OMe,-,-], [ZB827;G19,H,OEt,-,-], [ZB828;G19,H,OPh,-,-], [ZB829;G19,H,CF.sub.3,-,-], [ZB830;G19,H,F,-,-], [ZB831;G19,H,Cl,-,-], [ZB832;G19,H,Br,-,-], [ZB833;G19,H,CN,-,-], [ZB834;G20,H,H,-,-], [ZB835;G20,Me,H,-,-], [ZB836;G20,Et,H,-,-], [ZB837;G20,Pr,H,-,-], [ZB838;G20,i-Pr,H,-,-], [ZB839;G20,c-Pr,H,-,-], [ZB840;G20,Ph,H,-,-], [ZB841;G20,OMe,H,-,-], [ZB842;G20,OEt,H,-,-], [ZB843;G20,OPh,H,-,-], [ZB844;G20,CF.sub.3,H,-,-], [ZB845;G20, F,H,-,-], [ZB846;G20,Cl, H,-,-], [ZB847;G20,Br,H,-,-], [ZB848;G20,CN,H,-,-], [ZB849;G20,H,Me,-,-], [ZB850;G20,H,Et,-,-], [ZB851;G20,H,Pr,-,-], [ZB852;G20,H,i-Pr,-,-], [ZB853;G20,H,c-Pr,-,-], [ZB854;G20,H,Ph,-,-], [ZB855;G20,H,OMe,-,-], [ZB856;G20,H,OEt,-,-], [ZB857;G20,H,OPh,-,-], [ZB858;G20,H,CF.sub.3,-,-], [ZB859;G20,H,F,-,-], [ZB860;G20,H,Cl,-,-], [ZB861;G20,H,Br,-,-], [ZB862;G20,H,CN,-,-], [ZB863;G21,H,H,-,-], [ZB864;G21,Me,H,-,-], [ZB865;G21,Et,H,-,-], [ZB866;G21,Pr,H,-,-], [ZB867;G21,i-Pr,H,-,-], [ZB868;G21,c-Pr,H,-,-], [ZB869;G21,Ph,H,-,-], [ZB870;G21,OMe,H,-,-], [ZB871;G21,OEt,H,-,-], [ZB872;G21,OPh,H,-,-], [ZB873;G21,CF.sub.3,H,-,-], [ZB874;G21,F,H,-,-], [ZB875;G21,Cl,H,-,-], [ZB876;G21,Br,H,-,-], [ZB877;G21,CN,H,-,-], [ZB878;G21,H,Me,-,-], [ZB879;G21,H,Et,-,-], [ZB880;G21,H,Pr,-,-], [ZB881;G21,H,i-Pr,-,-], [ZB882;G21,H,c-Pr,-,-], [ZB883;G21,H,Ph,-,-], [ZB884;G21,H,OMe,-,-], [ZB885;G21,H,OEt,-,-], [ZB886;G21,H,OPh,-,-], [ZB887;G21,H,CF.sub.3,-,-], [ZB888;G21,H,F,-,-], [ZB889;G21,H,Cl,-,-], [ZB890;G21,H,Br,-,-], [ZB891;G21,H,CN,-,-], [ZB892;G22,H,H,-,-], [ZB893;G22,Me,H,-,-], [ZB894;G22,Et,H,-,-], [ZB895;G22,Pr,H,-,-], [ZB896;G22,i-Pr,H,-,-], [ZB897;G22,c-Pr,H,-,-], [ZB898;G22,Ph,H,-,-], [ZB899;G22,OMe,H,-,-], [ZB900;G22,OEt,H,-,-]
[ZB901;G22,OPh,H,-,-], [ZB902;G22,CF.sub.3,H,-,-], [ZB903;G22,F,H,-,-], [ZB904;G22,Cl,H,-,-], [ZB905;G22,Br,H,-,-], [ZB906;G22,CN,H,-,-], [ZB907;G22,H,Me,-,-], [ZB908;G22,H,Et,-,-], [ZB909;G22,H,Pr,-,-], [ZB910;G22,H,i-Pr,-,-], [ZB911;G22,H,c-Pr,-,-], [ZB912;G22,H,Ph,-,-], [ZB913;G22,H,OMe,-,-], [ZB914;G22,H,OEt,-,-], [ZB915;G22,H,OPh,-,-], [ZB916;G22,H,CF.sub.3-,-], [ZB917;G22,H,F,-,-], [ZB918;G22,H,Cl,-,-], [ZB919;G22,H,Br,-,-], [ZB920;G22,H,CN,-,-], [ZB921;G23,H,H,-,-], [ZB922;G23,Me,H,-,-], [ZB923;G23,Et,H,-,-], [ZB924;G23,Pr,H,-,-], [ZB925;G23,i-Pr,H,-,-], [ZB926;G23,c-Pr,H,-,-], [ZB927;G23,Ph,H,-,-], [ZB928;G23,OMe,H,-,-], [ZB929;G23,OEt,H,-,-], [ZB930;G23,OPh,H,-,-], [ZB931;G23,CF.sub.3,H,-,-], [ZB932;G23,F,H,-,-], [ZB933;G23,Cl,H,-,-], [ZB934;G23,Br,H,-,-], [ZB935;G23,CN,H,-,-], [ZB936;G23,H,Me,-,-], [ZB937;G23,H,Et,-,-], [ZB938;G23,H,Pr,-,-], [ZB939;G23,H,i-Pr,-,-], [ZB940;G23,H,c-Pr,-,-], [ZB941;G23,H,Ph,-,-], [ZB942;G23,H,OMe,-,-], [ZB943;G23,H,OEt,-,-], [ZB944;G23,H,OPh,-,-], [ZB945;G23,H,CF.sub.3,-,-], [ZB946;G23,H,F,-,-], [ZB947;G23,H,Cl,-,-], [ZB948;G23,H,Br,-,-], [ZB949;G23,H,CN,-,-], [ZB950;G24,H,H,-,-], [ZB951;G24,Me,H,-,-], [ZB952;G24,Et,H,-,-], [ZB953;G24,Pr,H,-,-], [ZB954;G24,i-Pr,H,-,-], [ZB955;G24,c-Pr,H,-,-], [ZB956;G24,Ph,H,-,-], [ZB957;G24,OMe,H,-,-], [ZB958;G24,OEt,H,-,-], [ZB959;G24,OPh,H,-,-], [ZB960;G24,CF.sub.3,H,-,-], [ZB961;G24,F,H,-,-], [ZB962;G24,Cl,H,-,-], [ZB963;G24,Br,H,-,-], [ZB964;G24,CN,H,-,-], [ZB965;G24,H,Me,-,-], [ZB966;G24,H,Et,-,-], [ZB967;G24,H,Pr,-,-], [ZB968;G24,H,i-Pr,-,-], [ZB969;G24,H,c-Pr,-,-], [ZB970;G24,H,Ph,-,-], [ZB971;G24,H,OMe,-,-], [ZB972;G24,H,OEt,-,-], [ZB973;G24,H,OPh,-,-], [ZB974;G24,H,CF.sub.3,-,-], [ZB975;G24,H,F,-,-], [ZB976;G24,H,Cl,-,-], [ZB977;G24,H,Br,-,-], [ZB978;G24,H,CN,-,-], [ZB979;G25,H,H,H,-], [ZB980;G25,H,Me,H,-], [ZB981;G25,H,Et,H,-], [ZB982;G25,H,Pr,H,-], [ZB983;G25,H,i-Pr,H,-], [ZB984;G25,H,c-Pr,H,-], [ZB985;G25,H,Ph,H,-], [ZB986;G25,H,OMe,H,-], [ZB987;G25,H,OEt,H,-], [ZB988;G25,H,OPh,H,-], [ZB989;G25,H,CF.sub.3,H,-], [ZB990;G25,H,F,H,-], [ZB991;G25,H,Cl,H,-], [ZB992;G25,H,Br,H,-], [ZB993;G25,H,CN,H,-], [ZB994;G25,H,H,Me,-], [ZB995;G25,H,H,Et,-], [ZB996;G25,H,H, Pr,-], [ZB997;G25,H,H, i-Pr,-], [ZB998;G25,H,H,c-Pr,-], [ZB999;G25,H,H,Ph,-], [ZB1000;G25,H,H,OMe,-]
[ZB1001;G25,H,H,OEt,-], [ZB1002;G25,H,H,OPh,-], [ZB1003;G25,H,H,CF.sub.3,-], [ZB1004;G25,H,H,F,-], [ZB1005;G25,H,H,Cl,-], [ZB1006;G25,H,H,Br,-], [ZB1007;G25,H,H,CN,-], [ZB1008;G25,Me,H,H,-], [ZB1009;G25,Me,Me,H,-], [ZB1010;G25,Me,Et,H,-], [ZB1011;G25,Me,Pr,H,-], [ZB1012;G25,Me,i-Pr,H,-], [ZB1013;G25,Me,c-Pr,H,-], [ZB1014;G25,Me,Ph,H,-], [ZB1015;G25,Me,OMe,H,-], [ZB1016;G25,Me,OEt,H,-], [ZB1017;G25,Me,OPh,H,-], [ZB1018;G25,Me,CF.sub.3,H,-], [ZB1019;G25,Me,F,H,-], [ZB1020;G25,Me,Cl,H,-], [ZB1021;G25,Me,Br,H,-], [ZB1022;G25,Me,CN,H,-], [ZB1023;G25,Me,H,Me,-], [ZB1024;G25,Me,H,Et,-], [ZB1025;G25,Me,H,Pr,-], [ZB1026;G25,Me,H,i-Pr,-], [ZB1027;G25,Me,H,c-Pr,-], [ZB1028;G25,Me,H,Ph,-], [ZB1029;G25,Me,H,OMe,-], [ZB1030;G25,Me,H,OEt,-], [ZB1031;G25,Me,H,OPh,-], [ZB1032;G25,Me,H,CF.sub.3,-], [ZB1033;G25,Me,H,F,-], [ZB1034;G25,Me,H,Cl,-], [ZB1035;G25,Me,H,Br,-], [ZB1036;G25,Me,H,CN,-], [ZB1037;G26,H,H,H,-], [ZB1038;G26,H,Me,H,-], [ZB1039;G26,H,Et,H,-], [ZB1040;G26,H,Pr,H,-], [ZB1041;G26,H,i-Pr,H,-], [ZB1042;G26,H,c-Pr,H,-], [ZB1043;G26,H,Ph,H,-], [ZB1044;G26,H,OMe,H,-], [ZB1045;G26,H,OEt,H,-], [ZB1046;G26,H,OPh,H,-], [ZB1047;G26,H,CF.sub.3,H,-], [ZB1048;G26,H,F,H,-], [ZB1049;G26,H,Cl,H,-], [ZB1050;G26,H,Br,H,-], [ZB1051;G26,H,CN,H,-], [ZB1052;G26,H,H,Me,-], [ZB1053;G26,H,H,Et,-], [ZB1054;G26,H,H,Pr,-], [ZB1055;G26,H,H,i-Pr,-], [ZB1056;G26,H,H,c-Pr,-], [ZB1057;G26,H,H,Ph,-], [ZB1058;G26,H,H,OMe,-], [ZB1059;G26,H,H,OEt,-], [ZB1060;G26,H,H,OPh,-], [ZB1061;G26,H,H,CF.sub.3,-], [ZB1062;G26,H,H,F,-], [ZB1063;G26,H,H,Cl,-], [ZB1064;G26,H,H,Br,-], [ZB1065;G26,H,H,CN,-], [ZB1066;G26,Me,H,H,-], [ZB1067;G26,Me,Me,H,-], [ZB1068;G26,Me,Et,H,-], [ZB1069;G26,Me,Pr,H,-], [ZB1070;G26,Me,i-Pr,H,-], [ZB1071;G26,Me,c-Pr,H,-], [ZB1072;G26,Me,Ph,H,-], [ZB1073;G26,Me,OMe,H,-], [ZB1074;G26,Me,OEt,H,-], [ZB1075;G26,Me,OPh,H,-], [ZB1076;G26,Me,CF.sub.3,H,-], [ZB1077;G26,Me,F,H,-], [ZB1078;G26,Me,Cl,H,-], [ZB1079;G26,Me,Br,H,-], [ZB1080;G26,Me,CN,H,-], [ZB1081;G26,Me,H,Me,-], [ZB1082;G26,Me,H,Et,-], [ZB1083;G26,Me,H,Pr,-], [ZB1084;G26,Me,H,i-Pr,-], [ZB1085;G26,Me,H,c-Pr,-], [ZB1086;G26,Me,H,Ph,-], [ZB1087;G26,Me,H,OMe,-], [ZB1088;G26,Me,H,OEt,-], [ZB1089;G26,Me,H,OPh,-], [ZB1090;G26,Me,H,CF.sub.3,-], [ZB1091;G26,Me,H,F,-], [ZB1092;G26,Me,H,Cl,-], [ZB1093;G26,Me,H,Br,-], [ZB1094;G26,Me,H,CN,-], [ZB1095;G27,H,H,H,-], [ZB1096;G27,Me,H,H,-], [ZB1097;G27,Et,H,H,-], [ZB1098;G27,Pr,H,H,-], [ZB1099;G27,i-Pr,H,H,-], [ZB1100;G27,c-Pr,H,H,-]
[ZB1101;G27, Ph,H, H,-], [ZB1102;G27,OMe,H,H,-], [ZB1103;G27,OEt,H,H,-], [ZB1104;G27,OPh,H,H,-], [ZB1105;G27,CF.sub.3,H,H,-], [ZB1106;G27,F,H,H,-], [ZB1107;G27,Cl,H,H,-], [ZB1108;G27,Br,H,H,-], [ZB1109;G27,CN,H,H,-], [ZB1110;G27,H,Me,H,-], [ZB1111;G27,H,Et,H,-], [ZB1112;G27,H,Pr,H,-], [ZB1113;G27,H,i-Pr,H,-], [ZB1114;G27,H,c-Pr,H,-], [ZB1115; G27, H, Ph, H,-], [ZB1116; G27, H, OMe, H,-], [ZB1117;G27,H,OEt,H,-], [ZB1118;G27,H,OPh,H,-], [ZB1119;G27,H,CF.sub.3,H,-], [ZB1120;G27,H,F,H,-], [ZB1121;G27,H,Cl,H,-], [ZB1122;G27,H,Br,H,-], [ZB1123;G27,H,CN,H,-], [ZB1124;G27,H,H,Me,-], [ZB1125;G27,H,H,Et,-], [ZB1126;G27,H,H,Pr,-], [ZB1127;G27,H,H,i-Pr,-], [ZB1128;G27,H,H,c-Pr,-], [ZB1129; G27, H, H, Ph,-], [ZB1130; G27, H,H,OMe,-], [ZB1131;G27,H,H,OEt,-], [ZB1132;G27,H,H,OPh,-], [ZB1133;G27,H,H,CF.sub.3,-], [ZB1134;G27,H,H,F,-], [ZB1135;G27,H,H,Cl,-], [ZB1136;G27,H,H,Br,-], [ZB1137;G27,H,H,CN,-], [ZB1138;G28,H,H,-,-], [ZB1139;G28,Me,H,-,-], [ZB1140;G28,Cl,H,-,-], [ZB1141;G28,CF.sub.3,H,-,-], [ZB1142;G28,H,Me,-,-], [ZB1143;G28,H,Cl,-,-], [ZB1144;G28,H,CF.sub.3,-,-], [ZB1145;G28,H,SH,-,-]

[0520] The compound represented by formula (1C) wherein R.sup.1 represents a chlorine atom, L represents an oxygen atom, m is 1, and a combination of a structure of G and the substituents of R.sup.X7, R.sup.X8, R.sup.X9, and R.sup.X10 which depend on a structure of G represents any combinations descried in the Combination B (hereinafter, referred to as Compound Class SX18).

[0521] The compound represented by formula (1C) wherein R.sup.1 represents a methyl group, L represents CH.sub.2, m is 1, and a combination of a structure of G and the substituents of R.sup.X7, R.sup.X8, R.sup.X9, and R.sup.X10 which depend on a structure of G represents any combinations descried in the Combination B (hereinafter, referred to as Compound Class SX19).

[0522] The compound represented by formula (1C) wherein R.sup.1 represents a chlorine atom, L represents CH.sub.2, m is 1, and a combination of a structure of G and the substituents of R.sup.X7, R.sup.X8, R.sup.X9, and R.sup.X10 which depend on a structure of G represents any combinations descried in the Combination B (hereinafter, referred to as Compound Class SX20).

[0523] The compound represented by formula (1C) wherein R.sup.1 represents a methyl group, L represents an oxygen atom, m is 2, and a combination of a structure of G and the substituents of R.sup.X7, R.sup.X8, R.sup.X9, and R.sup.X10 which depend on a structure of G represents any combinations descried in the Combination B (hereinafter, referred to as Compound Class SX21).

[0524] The compound represented by formula (1C) wherein R.sup.1 represents a chlorine atom, L represents an oxygen atom, m is 2, and a combination of a structure of G and the substituents of R.sup.X7, R.sup.X8, R.sup.X9, and R.sup.X10 which depend on a structure of G represents any combinations descried in the Combination B (hereinafter, referred to as Compound Class SX22).

[0525] The compound represented by formula (1C) wherein R.sup.1 represents a methyl group, L represents CH.sub.2, m is 2, and a combination of a structure of G and the substituents of R.sup.X7, R.sup.X8, R.sup.X9, and R.sup.X10 which depend on a structure of G represents any combinations descried in the Combination B (hereinafter, referred to as Compound Class SX23).

[0526] The compound represented by formula (1C) wherein R.sup.1 represents a chlorine atom, L represents CH.sub.2, m is 2, and a combination of a structure of G and the substituents of R.sup.X7, R.sup.X8, R.sup.X9, and R.sup.X10 which depend on a structure of G represents any combinations descried in the Combination B (hereinafter, referred to as Compound Class SX24).

[0527] The compound represented by formula (1C) wherein R.sup.1 represents a methyl group, L represents an oxygen atom, m is 3, and a combination of a structure of G and the substituents of R.sup.X7, R.sup.X8, R.sup.X9, and R.sup.X10 which depend on a structure of G represents any combinations descried in the Combination B (hereinafter, referred to as Compound Class SX25).

[0528] The compound represented by formula (1C) wherein R.sup.1 represents a chlorine atom, L represents an oxygen atom, m is 3, and a combination of a structure of G and the substituents of R.sup.X7, R.sup.X8, R.sup.X9, and R.sup.X10 which depend on a structure of G represents any combinations descried in the Combination B (hereinafter, referred to as Compound Class SX26).

[0529] The compound represented by formula (1C) wherein R.sup.1 represents a methyl group, L represents CH.sub.2, m is 3, and a combination of a structure of G and the substituents of R.sup.X7, R.sup.X8, R.sup.X9, and R.sup.X10 which depend on a structure of G represents any combinations descried in the Combination B (hereinafter, referred to as Compound Class SX27).

[0530] The compound represented by formula (1C) wherein R.sup.1 represents a chlorine atom, L represents CH.sub.2, m is 3, and a combination of a structure of G and the substituents of R.sup.X7, R.sup.X8, R.sup.X9, and R.sup.X10 which depend on a structure of G represents any combinations descried in the Combination B (hereinafter, referred to as Compound Class SX28).

[0531] A compound represented by formula (1D):

##STR00136##

wherein R.sup.1 represents a methyl group, L represents an oxygen atom, and R.sup.X11 represents any substituents selected from Group X, Group Y and Group Z (hereinafter, referred to as Compound Class SX29).
Group Y: a group consisting of Me, Ph, CH.sub.2Ph, (CH.sub.2).sub.2Ph, (CH.sub.2).sub.3Ph, 2-pyridyl, 3-pyridyl, 4-pyridyl, 2-thienyl, and 3-thienyl.
Group Z: a group consisting of 1-pyrrolidinyl, 1-piperidinyl, and 4-morpholinyl.

[0532] The compound represented by formula (1D) wherein R.sup.1 represents a chlorine atom, L represents an oxygen atom, and R.sup.X11 represents any substituents selected from Group X, Group Y and Group Z (hereinafter, referred to as Compound Class SX30).

[0533] The compound represented by formula (1D) wherein R.sup.1 represents a methyl group, L represents CH.sub.2, and R.sup.X11 represents any substituents selected from Group X, Group Y and Group Z (hereinafter, referred to as Compound Class SX31).

[0534] The compound represented by formula (1D) wherein R.sup.1 represents a chlorine atom, L represents CH.sub.2, and R.sup.X11 represents any substituents selected from Group X, Group Y and Group Z (hereinafter, referred to as Compound Class SX32).

[0535] A compound represented by formula (1E):

##STR00137##

wherein R.sup.1 represents a methyl group, L represents an oxygen atom, and R.sup.X12 represents any substituents selected from Group X and Group Y (hereinafter, referred to as Compound Class SX33).

[0536] The compound represented by formula (1E) wherein R.sup.1 represents a chlorine atom, L represents an oxygen atom, and R.sup.X12 represents any substituents selected from Group X and Group Y (hereinafter, referred to as Compound Class SX34).

[0537] The compound represented by formula (1E) wherein R.sup.1 represents a methyl group, L represents CH.sub.2, and R.sup.X12 represents any substituents selected from Group X and Group Y (hereinafter, referred to as Compound Class SX35).

[0538] The compound represented by formula (1E) wherein R.sup.1 represents a chlorine atom, L represents CH.sub.2, and R.sup.X12 represents any substituents selected from Group X and Group Y (hereinafter, referred to as Compound Class SX36).

[0539] A compound represented by formula (1F):

##STR00138##

wherein R.sup.1 represents a methyl group, L represents an oxygen atom, and R.sup.X13 represents a hydrogen atom, and R.sup.X14 represents any substituents selected from Group X and Group Y (hereinafter, referred to as Compound Class SX37).

[0540] The compound represented by formula (1F) wherein R.sup.1 represents a chlorine atom, L represents an oxygen atom, and R.sup.X13 represents a hydrogen atom, and R.sup.X14 represents any substituents selected from Group X and Group Y (hereinafter, referred to as Compound Class SX38).

[0541] The compound represented by formula (1F) wherein R.sup.1 represents a methyl group, L represents CH.sub.2, and R.sup.X13 represents a hydrogen atom, and R.sup.X14 represents any substituents selected from Group X and Group Y (hereinafter, referred to as Compound Class SX39).

[0542] The compound represented by formula (1F) wherein R.sup.1 represents a chlorine atom, L represents CH.sub.2, and R.sup.X13 represents a hydrogen atom, and R.sup.X14 represents any substituents selected from Group X and Group Y (hereinafter, referred to as Compound Class SX40).

[0543] The compound represented by formula (1F) wherein R.sup.1 represents a methyl group, L represents an oxygen atom, and R.sup.X13 represents a methyl group, and R.sup.X14 represents any substituents selected from Group X and Group Y (hereinafter, referred to as Compound Class SX41).

[0544] The compound represented by formula (1F) wherein R.sup.1 represents a chlorine atom, L represents an oxygen atom, and R.sup.X13 represents a methyl group, and R.sup.X14 represents any substituents selected from Group X and Group Y (hereinafter, referred to as Compound Class SX42).

[0545] The compound represented by formula (1F) wherein R.sup.1 represents a methyl group, L represents CH.sub.2, and R.sup.X13 represents a methyl group, and R.sup.X14 represents any substituents selected from Group X and Group Y (hereinafter, referred to as Compound Class SX43).

[0546] The compound represented by formula (1F) wherein R.sup.1 represents a chlorine atom, L represents CH.sub.2, and R.sup.X13 represents a methyl group, and R.sup.X14 represents any substituents selected from Group X and Group Y (hereinafter, referred to as Compound Class SX44).

[0547] The compound represented by formula (1F) wherein R.sup.1 represents a methyl group, L represents an oxygen atom, and R.sup.X13 represents an ethyl group, and R.sup.X14 represents any substituents selected from Group X and Group Y (hereinafter, referred to as Compound Class SX45).

[0548] The compound represented by formula (1F) wherein R.sup.1 represents a chlorine atom, L represents an oxygen atom, and R.sup.X13 represents an ethyl group, and R.sup.X14 represents any substituents selected from Group X and Group Y (hereinafter, referred to as Compound Class SX46).

[0549] The compound represented by formula (1F) wherein R.sup.1 represents a methyl group, L represents CH.sub.2, and R.sup.X13 represents an ethyl group, and R.sup.X14 represents any substituents selected from Group X and Group Y (hereinafter, referred to as Compound Class SX47).

[0550] The compound represented by formula (1F) wherein R.sup.1 represents a chlorine atom, L represents CH.sub.2, and R.sup.13 represents an ethyl group, and R.sup.X14 represents any substituents selected from Group X and Group Y (hereinafter, referred to as Compound Class SX48).

[0551] A compound represented by formula (1G):

##STR00139##

wherein R.sup.1 represents a methyl group, L represents an oxygen atom, R.sup.X13 represents a hydrogen atom, and a combination of R.sup.X2, R.sup.X3, R.sup.X4, R.sup.X5, and R.sup.X6 represents any combinations described in the Combination A (hereinafter, referred to as Compound Class SX49).

[0552] The compound represented by formula (1G) wherein R.sup.1 represents a chlorine atom, L represents an oxygen atom, and R.sup.X13 represents a hydrogen atom, and a combination of R.sup.X2, R.sup.X3, R.sup.X4, R.sup.X5, and R.sup.X6 represents any combinations described in the Combination A (hereinafter, referred to as Compound Class SX50).

[0553] The compound represented by formula (1G) wherein R.sup.1 represents a methyl group, L represents CH.sub.2, and R.sup.X13 represents a hydrogen atom, and a combination of R.sup.X2, R.sup.X3, R.sup.X4, R.sup.X5, and R.sup.X6 represents any combinations described in the Combination A (hereinafter, referred to as Compound Class SX51).

[0554] The compound represented by formula (1G) wherein R.sup.1 represents a chlorine atom, L represents CH.sub.2, and R.sup.X13 represents a hydrogen atom, and a combination of R.sup.X2, R.sup.X3, R.sup.X4, R.sup.X5, and R.sup.X6 represents any combinations described in the Combination A (hereinafter, referred to as Compound Class SX52).

[0555] The compound represented by formula (1G) wherein R.sup.1 represents a methyl group, L represents an oxygen atom, and R.sup.X13 represents a methyl group, and a combination of R.sup.X2, R.sup.X3, R.sup.X4, R.sup.X5, and R.sup.X6 represents any combinations described in the Combination A (hereinafter, referred to as Compound Class SX53).

[0556] The compound represented by formula (1G) wherein R.sup.1 represents a chlorine atom, L represents an oxygen atom, and R.sup.X13 represents a methyl group, and a combination of R.sup.X2, R.sup.X3, R.sup.X4, R.sup.X5, and R.sup.X6 represents any combinations described in the Combination A (hereinafter, referred to as Compound Class SX54).

[0557] The compound represented by formula (1G) wherein R.sup.1 represents a methyl group, L represents CH.sub.2, and R.sup.X13 represents a methyl group, and a combination of R.sup.X2, R.sup.X3, R.sup.X4, R.sup.X5, and R.sup.X6 represents any combinations described in the Combination A (hereinafter, referred to as Compound Class SX55).

[0558] The compound represented by formula (1G) wherein R.sup.1 represents a chlorine atom, L represents CH.sub.2, and R.sup.X13 represents a methyl group, and a combination of R.sup.X2, R.sup.X3, R.sup.X4, R.sup.X5, and R.sup.X6 represents any combinations described in the Combination A (hereinafter, referred to as Compound Class SX56).

[0559] The compound represented by formula (1G) wherein R.sup.1 represents a methyl group, L represents an oxygen atom, and R.sup.X13 represents an ethyl group, and a combination of R.sup.X2, R.sup.X3, R.sup.X4, R.sup.X5, and R.sup.X6 represents any combinations described in the Combination A (hereinafter, referred to as Compound Class SX57).

[0560] The compound represented by formula (1G) wherein R.sup.1 represents a chlorine atom, L represents an oxygen atom, and R.sup.X13 represents an ethyl group, and a combination of R.sup.X2, R.sup.X3, R.sup.X4, R.sup.X5, and R.sup.X6 represents any combinations described in the Combination A (hereinafter, referred to as Compound Class SX58).

[0561] The compound represented by formula (1G) wherein R.sup.1 represents a methyl group, L represents CH.sub.2, and R.sup.X13 represents an ethyl group, and a combination of R.sup.X2, R.sup.X3, R.sup.X4, R.sup.X5, and R.sup.X6 represents any combinations described in the Combination A (hereinafter, referred to as Compound Class SX59).

[0562] The compound represented by formula (1G) wherein R.sup.1 represents a chlorine atom, L represents CH.sub.2, and R.sup.X13 represents an ethyl group, and a combination of R.sup.X2, R.sup.X3, R.sup.X4, R.sup.X5, and R.sup.X6 represents any combinations described in the Combination A (hereinafter, referred to as Compound Class SX60).

[0563] A compound represented by formula (1H):

##STR00140##

wherein R.sup.1 represents a methyl group, L represents an oxygen atom, R.sup.X15 represents a hydrogen atom, and R.sup.X16 represents any substituents selected from Group X and Group Y (hereinafter, referred to as Compound Class SX61).

[0564] The compound represented by formula (1H) wherein R.sup.1 represents a chlorine atom, L represents an oxygen atom, and R.sup.X15 represents a hydrogen atom, and R.sup.X16 represents any substituents selected from Group X and Group Y (hereinafter, referred to as Compound Class SX62).

[0565] The compound represented by formula (1H) wherein R.sup.1 represents a methyl group, L represents CH.sub.2, and R.sup.X15 represents a hydrogen atom, and R.sup.X16 represents any substituents selected from Group X and Group Y (hereinafter, referred to as Compound Class SX63).

[0566] The compound represented by formula (1H) wherein R.sup.1 represents a chlorine atom, L represents CH.sub.2, and R.sup.X15 represents a hydrogen atom, and R.sup.X16 represents any substituents selected from Group X and Group Y (hereinafter, referred to as Compound Class SX64).

[0567] The compound represented by formula (1H) wherein R.sup.1 represents a methyl group, L represents an oxygen atom, and R.sup.X15 represents a methyl group, and R.sup.X16 represents any substituents selected from Group X and Group Y (hereinafter, referred to as Compound Class SX65).

[0568] The compound represented by formula (1H) wherein R.sup.1 represents a chlorine atom, L represents an oxygen atom, and R.sup.X15 represents a methyl group, and R.sup.X16 represents any substituents selected from Group X and Group Y (hereinafter, referred to as Compound Class SX66).

[0569] The compound represented by formula (1H) wherein R.sup.1 represents a methyl group, L represents CH.sub.2, and R.sup.X15 represents a methyl group, and R.sup.X16 represents any substituents selected from Group X and Group Y (hereinafter, referred to as Compound Class SX67).

[0570] The compound represented by formula (1H) wherein R.sup.1 represents a chlorine atom, L represents CH.sub.2, and R.sup.X15 represents a methyl group, and R.sup.X16 represents any substituents selected from Group X and Group Y (hereinafter, referred to as Compound Class SX68).

[0571] A compound represented by formula (1K):

##STR00141##

wherein R.sup.1 represents a methyl group, L represents an oxygen atom, and R.sup.X17 represents any substituents selected from Group X and Group Y (hereinafter, referred to as Compound Class SX69).

[0572] The compound represented by formula (1K) wherein R.sup.1 represents a chlorine atom, L represents an oxygen atom, and R.sup.X17 represents any substituents selected from Group X and Group Y (hereinafter, referred to as Compound Class SX70).

[0573] The compound represented by formula (1K) wherein R.sup.1 represents a methyl group, L represents CH.sub.2, and R.sup.X17 represents any substituents selected from Group X and Group Y (hereinafter, referred to as Compound Class SX71).

[0574] The compound represented by formula (1K) wherein R.sup.1 represents a chlorine atom, L represents CH.sub.2, and R.sup.X17 represents any substituents selected from Group X and Group Y (hereinafter, referred to as Compound Class SX72).

[0575] A compound represented by formula (1J):

##STR00142##

wherein R.sup.1 represents a methyl group, L represents an oxygen atom, R.sup.X10 represents a hydrogen atom, and R.sup.X19 represents any substituents selected from Group X and Group Y (hereinafter, referred to as Compound Class SX73).

[0576] The compound represented by formula (1J) wherein R.sup.1 represents a chlorine atom, L represents an oxygen atom, R.sup.X18 represents a hydrogen atom, and R.sup.X19 represents any substituents selected from Group X and Group Y (hereinafter, referred to as Compound Class SX74).

[0577] The compound represented by formula (1J) wherein R.sup.1 represents a methyl group, L represents CH.sub.2, R.sup.X18 represents a hydrogen atom, and R.sup.X19 represents any substituents selected from Group X and Group Y (hereinafter, referred to as Compound Class SX75).

[0578] The compound represented by formula (1J) wherein R.sup.1 represents a chlorine atom, L represents CH.sub.2, R.sup.X18 represents a hydrogen atom, and R.sup.X19 represents any substituents selected from Group X and Group Y (hereinafter, referred to as Compound Class SX76).

[0579] The compound represented by formula (1J) wherein R.sup.1 represents a methyl group, L represents an oxygen atom, R.sup.X18 represents a methyl group, and R.sup.X19 represents any substituents selected from Group X and Group Y (hereinafter, referred to as Compound Class SX77).

[0580] The compound represented by formula (1J) wherein R.sup.1 represents a chlorine atom, L represents an oxygen atom, R.sup.X18 represents a methyl group, and R.sup.X19 represents any substituents selected from Group X and Group Y (hereinafter, referred to as Compound Class SX78).

[0581] The compound represented by formula (1J) wherein R.sup.1 represents a methyl group, L represents CH.sub.2, R.sup.X18 represents a methyl group, and R.sup.X19 represents any substituents selected from Group X and Group Y (hereinafter, referred to as Compound Class SX79).

[0582] The compound represented by formula (1J) wherein R.sup.1 represents a chlorine atom, L represents CH.sub.2, R.sup.X18 represents a methyl group, and R.sup.X19 represents any substituents selected from Group X and Group Y (hereinafter, referred to as Compound Class SX80).

[0583] A compound represented by formula (2A):

##STR00143##

wherein R.sup.1 represents a methyl group, L represents an oxygen atom, and R.sup.X1 represents any substituents selected from Group X.

[0584] The compound represented by formula (2A) wherein R.sup.1 represents a chlorine atom, L represents an oxygen atom, and R.sup.X1 represents any substituents selected from Group X.

[0585] The compound represented by formula (2A) wherein R.sup.1 represents a methyl group, L represents CH.sub.2, and R.sup.X1 represents any substituents selected from Group X.

[0586] The compound represented by formula (2A) wherein R.sup.1 represents a chlorine atom, L represents CH.sub.2, and R.sup.X1 represents any substituents selected from Group X.

[0587] A compound represented by formula (2B):

##STR00144##

wherein R.sup.1 represents a methyl group, L represents an oxygen atom, m is 1, and a combination of R.sup.X2, R.sup.X3, R.sup.X4, R.sup.X5, and R.sup.X6 represents any combinations described in Combination A.

[0588] The compound represented by formula (2B) wherein R.sup.1 represents a chlorine atom, L represents an oxygen atom, m is 1, and a combination of R.sup.X2, R.sup.X3, R.sup.X4, R.sup.X5, and R.sup.X6 represents any combinations described in Combination A.

[0589] The compound represented by formula (2B) wherein R.sup.1 represents a methyl group, L represents CH.sub.2, m is 1, and a combination of R.sup.X2, R.sup.X3, R.sup.X4, R.sup.X5, and R.sup.X6 represents any combinations described in Combination A.

[0590] The compound represented by formula (2B) wherein R.sup.1 represents a chlorine atom, L represents CH.sub.2, m is 1, and a combination of R.sup.X2, R.sup.X3, R.sup.X4, R.sup.X5, and R.sup.X6 represents any combinations described in Combination A.

[0591] The compound represented by formula (2B) wherein R.sup.1 represents a methyl group, L represents an oxygen atom, m is 2, and a combination of R.sup.X2, R.sup.X3, R.sup.X4, R.sup.X5, and R.sup.X6 represents any combinations described in Combination A.

[0592] The compound represented by formula (2B) wherein R.sup.1 represents a chlorine atom, L represents an oxygen atom, m is 2, and a combination of R.sup.X2, R.sup.X3, R.sup.X4, R.sup.X5, and R.sup.X6 represents any combinations described in Combination A.

[0593] The compound represented by formula (2B) wherein R.sup.1 represents a methyl group, L represents CH.sub.2, m is 2, and a combination of R.sup.X2, R.sup.X3, R.sup.X4, R.sup.X5, and R.sup.X6 represents any combinations described in Combination A.

[0594] The compound represented by formula (2B) wherein R.sup.1 represents a chlorine atom, L represents CH.sub.2, m is 2, and a combination of R.sup.X2, R.sup.X3, R.sup.X4, R.sup.X5, and R.sup.X6 represents any combinations described in Combination A.

[0595] The compound represented by formula (2B) wherein R.sup.1 represents a methyl group, L represents an oxygen atom, m is 3, and a combination of R.sup.X2, R.sup.X3, R.sup.X4, R.sup.X5, and R.sup.X6 represents any combinations described in Combination A.

[0596] The compound represented by formula (2B) wherein R.sup.1 represents a chlorine atom, L represents an oxygen atom, m is 3, and a combination of R.sup.X2, R.sup.X3, R.sup.X4, R.sup.X5, and R.sup.X6 represents any combinations described in Combination A.

[0597] The compound represented by formula (2B) wherein R.sup.1 represents a methyl group, L represents CH.sub.2, m is 3, and a combination of R.sup.X2, R.sup.X3, R.sup.X4, R.sup.X5, and R.sup.X6 represents any combinations described in Combination A.

[0598] The compound represented by formula (2B) wherein R.sup.1 represents a chlorine atom, L represents CH.sub.2, m is 3, and a combination of R.sup.X2, R.sup.X3, R.sup.X4, R.sup.X5, and R.sup.X6 represents any combinations described in Combination A.

[0599] A compound represented by formula (2C):

##STR00145##

wherein R.sup.1 represents a methyl group, L represents an oxygen atom, m is 1, and a combination of a structure of G and the substituents of R.sup.X7, R.sup.X8, R.sup.X9, and R.sup.X10 which depend on a structure of G represents any combinations descried in the Combination B.

[0600] A compound represented by formula (2C) wherein R.sup.1 represents a chlorine atom, L represents an oxygen atom, m is 1, and a combination of a structure of G and the substituents of R.sup.X7, R.sup.X8, R.sup.X9, and R.sup.X10 which depend on a structure of G represents any combinations descried in the Combination B.

[0601] A compound represented by formula (2C) wherein R.sup.1 represents a methyl group, L represents CH.sub.2, m is 1, and a combination of a structure of G and the substituents of R.sup.X7, R.sup.X8, R.sup.X9, and R.sup.X10 which depend on a structure of G represents any combinations descried in the Combination B.

[0602] A compound represented by formula (2C) wherein R.sup.1 represents a chlorine atom, L represents CH.sub.2, m is 1, and a combination of a structure of G and R.sup.X7, R.sup.X8, R.sup.X9, and R.sup.X10 which depend on a structure of G represents any combinations descried in the Combination B.

[0603] A compound represented by formula (2C) wherein R.sup.1 represents a methyl group, L represents an oxygen atom, m is 2, and a combination of a structure of G and R.sup.X7, R.sup.X8, R.sup.X9, and R.sup.X10 which depend on a structure of G represents any combinations descried in the Combination B.

[0604] A compound represented by formula (2C) wherein R.sup.1 represents a chlorine atom, L represents an oxygen atom, m is 2, and a combination of a structure of G and R.sup.X7, R.sup.X8, R.sup.X9, and R.sup.X10 which depend on a structure of G represents any combinations descried in the Combination B.

[0605] A compound represented by formula (2C) wherein R.sup.1 represents a methyl group, L represents CH.sub.2, m is 2, and a combination of a structure of G and the substituents of R.sup.X7, R.sup.X8, R.sup.X9, and R.sup.X10 which depend on a structure of G represents any combinations descried in the Combination B.

[0606] A compound represented by formula (2C) wherein R.sup.1 represents a chlorine atom, L represents CH.sub.2, m is 2, and a combination of a structure of G and the substituents of R.sup.X7, R.sup.X8, R.sup.X9, and R.sup.X10 which depend on a structure of G represents any combinations descried in the Combination B.

[0607] A compound represented by formula (2C) wherein R.sup.1 represents a methyl group, L represents an oxygen atom, m is 3, and a combination of a structure of G and the substituents of R.sup.X7, R.sup.X8, R.sup.X9, and R.sup.X10 which depend on a structure of G represents any combinations descried in the Combination B.

[0608] A compound represented by formula (2C) wherein R.sup.1 represents a chlorine atom, L represents an oxygen atom, m is 3, and a combination of a structure of G and the substituents of R.sup.X7, R.sup.X8, R.sup.X9, and R.sup.X10 which depend on a structure of G represents any combinations descried in the Combination B.

[0609] A compound represented by formula (2C) wherein R.sup.1 represents a methyl group, L represents CH.sub.2, m is 3, and a combination of a structure of G and the substituents of R.sup.X7, R.sup.X8, R.sup.X9, and R.sup.X10 which depend on a structure of G represents any combinations descried in the Combination B.

[0610] A compound represented by formula (2C) wherein R.sup.1 represents a chlorine atom, L represents CH.sub.2, m is 3, and a combination of a structure of G and the substituents of R.sup.X7, R.sup.X8, R.sup.X9, and R.sup.X10 which depend on a structure of G represents any combinations descried in the Combination B.

[0611] A compound represented by formula (2D):

##STR00146##

wherein R.sup.1 represents a methyl group, L represents an oxygen atom, and R.sup.X11 represents any substituents selected from Group X, Group Y and Group Z.

[0612] The compound represented by formula (2D) wherein R.sup.1 represents a chlorine atom, L represents an oxygen atom, and R.sup.X11 represents any substituents selected from Group X, Group Y and Group Z.

[0613] The compound represented by formula (2D) wherein R.sup.1 represents a methyl group, L represents CH.sub.2, and R.sup.X11 represents any substituents selected from Group X, Group Y and Group Z.

[0614] The compound represented by formula (2D) wherein R.sup.1 represents a chlorine atom, L represents CH.sub.2, and R.sup.X11 represents any substituents selected from Group X, Group Y and Group Z.

[0615] A compound represented by formula (2F):

##STR00147##

wherein R.sup.1 represents a methyl group, L represents an oxygen atom, R.sup.X13 represents a hydrogen atom, and R.sup.X14 represents any substituents selected from Group X and Group Y.

[0616] A compound represented by formula (2F) wherein R.sup.1 represents a chlorine atom, L represents an oxygen atom, R.sup.X13 represents a hydrogen atom, and R.sup.X14 represents any substituents selected from Group X and Group Y.

[0617] A compound represented by formula (2F) wherein R.sup.1 represents a methyl group, L represents CH.sub.2, R.sup.X13 represents a hydrogen atom, and R.sup.X14 represents any substituents selected from Group X and Group Y.

[0618] A compound represented by formula (2F) wherein R.sup.1 represents a chlorine atom, L represents CH.sub.2, R.sup.X13 represents a hydrogen atom, and R.sup.X14 represents any substituents selected from Group X and Group Y.

[0619] A compound represented by formula (2F) wherein R.sup.1 represents a methyl group, L represents an oxygen atom, R.sup.X13 represents a methyl group, and R.sup.X14 represents any substituents selected from Group X and Group Y.

[0620] A compound represented by formula (2F) wherein R.sup.1 represents a chlorine atom, L represents an oxygen atom, R.sup.X13 represents a methyl group, and R.sup.X14 represents any substituents selected from Group X and Group Y.

[0621] A compound represented by formula (2F) wherein R.sup.1 represents a methyl group, L represents CH.sub.2, R.sup.X13 represents a methyl group, and R.sup.X14 represents any substituents selected from Group X and Group Y.

[0622] A compound represented by formula (2F) wherein R.sup.1 represents a chlorine atom, L represents CH.sub.2, R.sup.X13 represents a methyl group, and R.sup.X14 represents any substituents selected from Group X and Group Y.

[0623] A compound represented by formula (2F) wherein R.sup.1 represents a methyl group, L represents an oxygen atom, R.sup.X13 represents an ethyl group, and R.sup.X14 represents any substituents selected from Group X and Group Y.

[0624] A compound represented by formula (2F) wherein R.sup.1 represents a chlorine atom, L represents an oxygen atom, R.sup.X13 represents an ethyl group, and R.sup.X14 represents any substituents selected from Group X and Group Y.

[0625] A compound represented by formula (2F) wherein R.sup.1 represents a methyl group, L represents CH.sub.2, R.sup.X13 represents an ethyl group, and R.sup.X14 represents any substituents selected from Group X and Group Y.

[0626] A compound represented by formula (2F) wherein R.sup.1 represents a chlorine atom, L represents CH.sub.2, R.sup.X13 represents an ethyl group, and R.sup.X14 represents any substituents selected from Group X and Group Y.

[0627] A compound represented by formula (3A):

##STR00148##

wherein R.sup.X1 represents any substituents selected from Group X.

[0628] A compound represented by formula (3B):

##STR00149##

wherein m is 1, and a combination of R.sup.X2, R.sup.X3, R.sup.X4, R.sup.X5 and R.sup.X6 represents any combinations described in the Combination A.

[0629] The compound represented by formula (3B) wherein m is 2, and a combination of R.sup.X2, R.sup.X3, R.sup.X4, R.sup.X5 and R.sup.X6 represents any combinations described in the Combination A.

[0630] The compound represented by formula (3B) wherein m is 3, and a combination of R.sup.X2, R.sup.X3, R.sup.X4, R.sup.X5 and R.sup.X6 represents any combinations described in the Combination A.

[0631] A compound represented by formula (3C):

##STR00150##

wherein m is 1, and a combination of a structure of G and the substituents of R.sup.X7, R.sup.X8, R.sup.X9, and R.sup.X10 which depend on a structure of G represents any combinations descried in the Combination B.

[0632] The compound represented by formula (3C) wherein m is 2, and a combination of a structure of G and the substituents of R.sup.X7, R.sup.X8, R.sup.X9, and R.sup.X10 which depend on a structure of G represents any combinations descried in the Combination B.

[0633] The compound represented by formula (3C) wherein m is 3, and a combination of a structure of G and the substituents of R.sup.X7, R.sup.X8, R.sup.X9, and R.sup.X10 which depend on a structure of G represents any combinations descried in the Combination B.

[0634] A compound represented by formula (3D):

##STR00151##

wherein R.sup.X11 represents any substituents selected from Group X, Group Y and Group Z.

[0635] A compound represented by formula (3F):

##STR00152##

wherein R.sup.X13 represents a hydrogen atom, and R.sup.X14 represents any substituents selected from Group X and Group Y.

[0636] The compound represented by formula (3F) wherein R.sup.X13 represents a methyl group, and R.sup.X14 represents any substituents selected from Group X and Group Y.

[0637] The compound represented by formula (3F) wherein R.sup.X13 represents an ethyl group, and R.sup.X14 represents any substituents selected from Group X and Group Y.

[0638] A compound represented by formula (4A):

##STR00153##

wherein L represents an oxygen atom, and R.sup.1 represents any substituents selected from Group W.
Group W: a group consisting of Me, Et, Pr, c-Pr, CF.sub.3, F, C1, Br, and I.

[0639] The compound represented by formula (4A) wherein L represents CH.sub.2, and R.sup.1 represents any substituents selected from Group W.

[0640] A compound represented by formula (5A):

##STR00154##

wherein R.sup.X1 represents any substituents selected from Group X.

[0641] A compound represented by formula (5B):

##STR00155##

wherein m is 1, and a combination of R.sup.X2, R.sup.X3, R.sup.X4, R.sup.X5, and R.sup.X6 represents any combinations described in Combination A.

[0642] The compound represented by formula (5B) wherein m is 2, and a combination of R.sup.X2, R.sup.X3, R.sup.X4, R.sup.X5, and R.sup.X6 represents any combinations described in Combination A.

[0643] The compound represented by formula (5B) wherein m is 3, and a combination of R.sup.X2, R.sup.X3, R.sup.X4, R.sup.X5, and R.sup.X6 represents any combinations described in Combination A.

[0644] A compound represented by formula (5C):

##STR00156##

wherein m is 1, and a combination of a structure of G and the substituents of R.sup.X7, R.sup.X8, R.sup.X9, and R.sup.X10 which depend on a structure of G represents any combinations descried in the Combination B.

[0645] The compound represented by formula (5C) wherein m is 2, and a combination of a structure of G and the substituents of R.sup.X7, R.sup.X8, R.sup.X9, and R.sup.X10 which depend on a structure of G represents any combinations descried in the Combination B.

[0646] The compound represented by formula (5C) wherein m is 3, and a combination of a structure of G and the substituents of R.sup.X7, R.sup.X8, R.sup.X9, and R.sup.X10 which depend on a structure of G represents any combinations descried in the Combination B.

[0647] A compound represented by formula (5D):

##STR00157##

wherein R.sup.X11 represents any substituents selected from Group X, Group Y and Group Z.

[0648] A compound represented by formula (5F):

##STR00158##

wherein R.sup.X13 represents a hydrogen atom, and R.sup.X14 represents any substituents selected from Group X and Group Y.

[0649] The compound represented by formula (5F) wherein R.sup.X13 represents a methyl group, and R.sup.X14 represents any substituents selected from Group X and Group Y.

[0650] The compound represented by formula (5F) wherein R.sup.X13 represents an ethyl group, and R.sup.X14 represents any substituents selected from Group X and Group Y.

[0651] Next, the formulation Examples of the Present compound is described. The “parts” represents “part by weight” unless otherwise specified. Also the present compound S represents any compounds described as Compound Class SX1 to SX80.

Formulation Example 1

[0652] Fifty (50) parts of any one of the present compound S, 3 parts of calcium lignin sulfonate, 2 parts of magnesium lauryl sulfate, and 45 parts of synthetic hydrated silicon dioxide are well mixed-grinding to obtain a formulation.

Formulation Example 2

[0653] Twenty (20) parts of any one of the present compound S, and 1.5 parts of sorbitan trioleate are mixed with 28.5 parts of an aqueous solution containing 2 parts of polyvinyl alcohol, and the mixture is then finely-ground by a wet grinding method. To the mixture is then added 40 parts of an aqueous solution containing 0.05 parts of xanthan gum and 0.1 parts of magnesium aluminum silicate, and 10 parts of propylene glycol is further added thereto, and the mixture is mixed with starring to obtain a formulation.

Formulation Example 3

[0654] Two (2) parts of any one of the present compound S, 88 parts of kaolin clay and 10 parts of talc are mixed-grinding thoroughly to obtain a formulation.

Formulation Example 4

[0655] Five (5) parts of any one of the present compound S, 14 parts of polyoxyethylene styryl phenyl ether, 6 parts of calcium dodecylbenzene sulfonate and 75 parts of xylene are mixed-grinding thoroughly to obtain a formulation.

Formulation Example 5

[0656] Two (2) parts of any one of the present compound S, 1 part of synthetic hydrated silicon dioxide, 2 parts of calcium lignosulfonate, 30 parts of bentonite and 65 parts of kaolin clay are mixed-grinding, and thereto is added water, and the mixture is well kneaded and is then granulated and dried to obtain a formulation.

Formulation Example 6

[0657] Twenty (20) parts of the present compound S, 35 parts of a mixture of white carbon and ammonium polyoxyethylene alkyl ether sulfate (weight ratio is 1:1) and appropriate amount of water is mixed to make the total amount thereof 100 parts, and the mixture is then finely-ground with a grinder to obtain a formulation.

[0658] Next, Test Examples are described.

[0659] The untreated groups in Test Example 1 to Test Exmaple 9 represent tested groups in which the same conditions as those of each of the Test Examples were conducted except that DMSO was dispensed in the place of a DMSO diluted solution comprising the present compound. Also the untreated groups in Test Exmaple 10 to Test Exmaple 22 represent tested groups in which an aqueous diluted solution of a formulation comprising the present compound is not applied.

Test Example 1: Control Test Against Wheat Septoria Leaf Blotch Fungus (Septoria tritici)

[0660] The present compound 1 to 16, 18 to 23, 25, 26, 28 to 30, 33 to 35, 37, 38 to 40, 42 to 52, 54 to 87, 89, or 90 was diluted with DMSO so as to contain 150 ppm, and 1 μL of the dilution solutions were dispensed into titer plate (96 well), and thereafter, thereto was then dispensed 150 μL of a potato dextrose broth (PDB broth) to which conidia of Septoria tritici were inoculated in advance. This plate was cultured at 18° C. for 5 days, thereby allowing Septoria tritici to undergo proliferation, and the absorbance at 550 nm of each well of the titer plate was then measured to determine a degree of growth of Septoria tritici. As a result, every of the growth in the well in treated groups treated with each of the present compounds showed 50% or less compared to the growth in an untreated well.

Test Example 2: Control Test Against Soybean Anthracnose Fungus (Colletotrichum truncatum)

[0661] The present compound 2 to 16, 18 to 20, 25, 26, 29, 38, 40, 42 to 44, 46 to 49, 51, 52, 55, 57 to 64, 71, or 76 was diluted with DMSO so as to contain 150 ppm, and 1 μL of the dilution solutions were dispensed into titer plate (96 well), and thereafter, thereto was then dispensed 150 μL of a potato dextrose broth (PDB broth) to which conidia of Colletotrichum truncatum were inoculated in advance. This plate was cultured at 18° C. for 4 days, thereby allowing Colletotrichum truncatum to undergo proliferation, and the absorbance at 550 nm of each well of the titer plate was then measured to determine a degree of growth of the Colletotrichum truncatum. As a result, every of the growth in the well in treated groups treated with each of the present compounds showed 50% or less compared to the growth in an untreated well.

Test Example 3: Control Test Against Cucurbitaceae Phytophthora Rot Fungus (Phytophthora capsici)

[0662] The present compound 1 to 20, 23, 25, 26, 29, 34, 37, 38, 40 to 49, 51, 52, 54 to 64, 68, 71, 73 to 76, 80, 89, or 90 was diluted with DMSO so as to contain 150 ppm, and 1 μL of the dilution solutions were dispensed into titer plate (96 well), and thereafter, thereto was then dispensed 150 μL of a potato dextrose broth (PDB broth) to which spores of Phytophthora capsici were inoculated in advance. This plate was cultured at 27° C. for 3 days, thereby allowing Phytophthora capsici to undergo proliferation, and the absorbance at 550 nm of each well of the titer plate was then measured to determine a degree of growth of the Phytophthora capsici. As a result, every of the growth in the well in treated groups treated with each of the present compounds showed 50% or less compared to the growth in an untreated well.

Test Example 4: Control Test Against Seedling Blight Fungus (Pythium ultimum)

[0663] The present compound 1 to 20, 23, 25, 26, 29, 34, 37, 38, 40 to 49, 51, 52, 54 to 64, 66, 68, 71 to 76, 79 to 81, 84 to 86, 89, or 90 was diluted with DMSO so as to contain 150 ppm, and 1 μL of the dilution solutions were dispensed into titer plate (96 well), and thereafter, thereto was then dispensed 150 μL of a potato dextrose broth (PDB broth) to which spores of Pythium ultimum were inoculated in advance. This plate was cultured at 23° C. for 5 days, thereby allowing Pythium ultimum to undergo proliferation, and the absorbance at 550 nm of each well of the titer plate was then measured to determine a degree of growth of the Pythium ultimum. As a result, every of the growth in the well in treated groups treated with each of the present compounds showed 50% or less compared to the growth in an untreated well.

Test Example 5: Control Test Against Corn Smut Fungus (Ustilago maydis)

[0664] The present compound 1 to 20, 23, 25, 26, 29, 30, 34, 37 to 49, 51, 52, 54 to 64, 68, 71 to 76, 78 to 87, 89, or 90 was diluted with DMSO so as to contain 150 ppm, and 1 μL of the dilution solutions were dispensed into titer plate (96 well), and thereafter, thereto was then dispensed 150 μL of a potato dextrose broth (PDB broth) to which conidia of Ustilago maydis were inoculated in advance. This plate was cultured at 18° C. for 4 days, thereby allowing Ustilago maydis to undergo proliferation, and the absorbance at 550 nm of each well of the titer plate was then measured to determine a degree of growth of the Ustilago maydis. As a result, every of the growth in the well in treated groups treated with each of the present compounds showed 50% or less compared to the growth in an untreated well.

Test Example 6: Control Test Against Barley Scald Fungus (Rhynchosporium secalis)

[0665] The present compound 1 to 20, 23, 25, 26, 29 to 49, 51, 52, 54 to 64, 66 to 68, 71 to 87, 89, or 90 was diluted with DMSO so as to contain 150 ppm, and 1 μL of the dilution solutions were dispensed into titer plate (96 well), and thereafter, thereto was then dispensed 150 μL of a potato dextrose broth (PDB broth) to which conidia of Rhynchosporium secalis were inoculated in advance. This plate was cultured at 18° C. for 7 days, thereby allowing Rhynchosporium secalis to undergo proliferation, and the absorbance at 550 nm of each well of the titer plate was then measured to determine a degree of growth of the Rhynchosporium secalis. As a result, every of the growth in the well in treated groups treated with each of the present compounds showed 50% or less compared to the growth in an untreated well.

Test Example 7: Control Test Against Cucumber Botrytis Rot Fungus (Botrytis cinerea)

[0666] The present compound 1 to 20, 23, 25, 26, 29 to 34, 36 to 49, 51, 52, 54 to 64, 66, 68, 71 to 85, 87, 89, or 90 was diluted with DMSO so as to contain 150 ppm, and 1 μL of the dilution solutions were dispensed into titer plate (96 well), and thereafter, thereto was then dispensed 150 μL of a potato dextrose broth (PDB broth) to which conidia of Botrytis cinerea were inoculated in advance. This plate was cultured at 18° C. for 4 days, thereby allowing Botrytis cinerea to undergo proliferation, and the absorbance at 550 nm of each well of the titer plate was then measured to determine a degree of growth of the Botrytis cinerea. As a result, every of the growth in the well in treated groups treated with each of the present compounds showed 50% or less compared to the growth in an untreated well.

Test Example 8: Control Test Against Peach Scab Fungus (Cladosporium carpophilum)

[0667] The present compound 1 to 20, 23, 25, 26, 29 to 49, 51, 52, 54 to 64, 66 to 68, 71 to 87, 89, or 90 was diluted with DMSO so as to contain 150 ppm, and 1 μL of the dilution solutions were dispensed into titer plate (96 well), and thereafter, thereto was then dispensed 150 μL of a potato dextrose broth (PDB broth) to which conidia of Cladosporium carpophilum were inoculated in advance. This plate was cultured at 18° C. for 5 days, thereby allowing Cladosporium carpophilum to undergo proliferation, and the absorbance at 550 nm of each well of the titer plate was then measured to determine a degree of growth of the Cladosporium carpophilum. As a result, every of the growth in the well in treated groups treated with each of the present compounds showed 50% or less compared to the growth in an untreated well.

Test Example 9: Control Test Against Rice Brown Spot Fungus (Cochliobolus miyabeanus)

[0668] The present compound 28, 30 to 33, 35, 37, 39, 50, 66, 67, 69, 70, 72 to 75, 77 to 89, or 90 was diluted with DMSO so as to contain 150 ppm, and 1 μL of the dilution solutions were dispensed into titer plate (96 well), and thereafter, thereto was then dispensed 150 μL of a potato dextrose broth (PDB broth) to which conidia of Cochliobolus miyabeanus were inoculated in advance. This plate was cultured at 23° C. for 3 days, thereby allowing Cochliobolus miyabeanus to undergo proliferation, and the absorbance at 550 nm of each well of the titer plate was then measured to determine a degree of growth of the Cochliobolus miyabeanus. As a result, every of the growth in the well in treated groups treated with each of the present compounds showed 50% or less compared to the growth in an untreated well.

Test Example 10: Control Test Against Soybean Rust (Phakopsora pachyrhizi)

[0669] Soybean leaf (cv; Kurosengoku) was punched out to 1 cm diameter to prepare a leaf disk. Each 1 mL of an agar medium (agar concentration 1.2%) was dispensed in each well of 24 well microplate. A piece of the leaf disk was placed on agar medium on each well. To a mixture of 0.5 μL of Sorpol (registered trademark) 1200KX, 4.5 μL of DMSO, and 5 μL of xylene was added 20 μL of a solution containing 10000 ppm of the test compound in DMSO. The resulting mixture was diluted with ion exchange water to prepare a mixture containing a predetermined concentration of the test compound. The resulting mixture was sprayed in 10 μL per one leaf disk. After 1 day, an aqueous suspension of conidia of Phakopsora pachyrhizi having an amino acid substitution of F129L on mitochondrial cytochrome b protein (1.0×10.sup.5/mL) was inoculated onto the leaf disks. After the inoculation, the microplate was placed in a growth chamber (light on for 6 hours, light off for 18 hours, 23° C. temperature, 60% humidity). After 1 day, the leaf disks were air-dried to disappear water droplets on the surface of the leaf disk, and the microplate was placed again in the growth chamber for 12 days. Thereafter, a lesion area of soybean rust disease was assessed. As a result, lesion areas in the leaf disk treated with any one of the present compounds 1 to 10, 15 to 20, 23, 28 to 31, 33 to 35, 37, 39, 40, 50, 55, 56, 66 to 68, 70, 71 to 87, 89, or 90 as a tested compound at a prescribed concentration of 50 ppm showed 30% or more compared to the lesion areas in an untreated leaf disk.

Test Example 11: Control Test Against Rice Blast (Pyricularia oryzae)

[0670] Each of plastic pots was filled with soil and thereto rice (cv; HINOHIKARI) seeds were sown and the plants were grown in a greenhouse for 20 days. Thereafter, the present compound 19, 44, or 80, each of which was made to a formulation according to the similar method to that of Formulation Example 6, was mixed with water so as to be 200 ppm. The mixtures were sprayed to foliar parts so as to adhere adequately on the leaves of the above-mentioned rice. After spraying the mixtures, the rices were air-dried and were placed at 24° C. during daytime and 20° C. during nighttime under a high humidity for 6 to 7 days while the above-mentioned spraying-treated rice were contacted rice seedlings (cv; Hinohikari) infected by Pyricularia oryzae, and a lesion area was observed. As a result, every of the lesion areas in rice treated with each of the present compounds showed 30% or less compared to the lesion are in an untreated rice.

Test Example 12: Control Test Against Barley Net Blotch (Pyrenophora teres)

[0671] Each of plastic pots was filled with soil and thereto barley (cv; NISHINOHOSHI) seeds were sown and the barleys were grown in a greenhouse for 7 days. Thereafter, the present compound 2, 4 to 6, 13, 14, 16, 18 to 20, 26, 34, 39, 46 to 49, 51, 52, 54, 55, 57, 58, 64, 67, 68, 75 to 77, 80 to 83, 85 to 88, or 89, each of which was made to a formulation according to the similar method to that of Formulation Example 6, was mixed with water so as to be a prescribed concentration (200 ppm). The resulting mixtures were sprayed to foliar parts so as to adhere adequately on the leaves of the above-mentioned barley. After spraying the mixtures, the barleys were air-dried and after 1 day, an aqueous suspension of the conidia of Pyrenophora teres was spraying-inoculated. After the inoculation, the barleys were placed at 23° C. during daytime and 20° C. during nighttime under a high humidity for 3 day and then cultivated in a greenhouse for 7 days, and a lesion area was observed. As a result, every of the lesion areas in barleys treated with each of the present compounds showed 30% or less compared to the lesion area in an untreated barley.

Test Example 13: Control Test Against Cucumber Downy Mildew (Pseudoperonospora cubensis)

[0672] Each of plastic pots was filled with soil and thereto cucumber (cv; SAGAMIHANJIRO) seeds were sown and the cucumbers were grown in a greenhouse for 12 days. Thereafter, the present compound 2, 47, or 61, each of which was made to a formulation according to the similar method to that of Formulation Example 6, was mixed with water so as to be 200 ppm. The mixtures were sprayed to foliar parts so as to adhere adequately on the leaves of the above-mentioned cucumber. After spraying the mixtures, the cucumbers were air-dried and after 1 day, an aqueous suspension of a spore of Pseudoperonospora cubensis was spraying-inoculated. After the inoculation, the cucumbers were placed firstly at 23° C. under a high humidity for 1 day and were then cultivated in a greenhouse for 10 days, and a lesion area was observed. As a result, every of the lesion areas in cucumbers treated with each of the present compounds showed 30% or less compared to the lesion area in an untreated cucumber.

Test Example 14: Control Test Against Wheat Brown Rust (Puccinia recondita)

[0673] Each of plastic pots was filled with soil and thereto wheat (cv; SHIROGANE) seeds were sown and the wheats were grown in a greenhouse for 9 days. The present compound 2 to 6, 10 to 16, 18, 19, 20, 25, 26, 29, 31, 32, 34, 35, 39 to 42, 46, 47, 49, 52 to 64, 66 to 68, 73, 75 to 78, 80, 81, 83 to 89, or 90, each of which was made to a formulation according to the similar method to that of Formulation Example 6, was mixed with water so as to be 200 ppm, and the mixtures were sprayed to foliar parts so as to adhere adequately on the leaves of the above-mentioned wheat. After spraying the mixtures, the wheats were air-dried and were then cultivated at 20° C. under lighting for 5 to 7 days. The conidia of Puccinia recondita were sprinkling-inoculated. After the inoculation, the wheats were placed under a dark and humid condition at 23° C. for 1 day and were then cultivated at 20° C. under lighting for 8 days, and a lesion area was observed. As a result, every of the lesion areas in wheats treated with each of the present compounds showed 30% or less compared to the lesion area in an untreated wheat.

Test Example 15: Control Test Against Septoria Leaf Blotch (Septoria tritici)

[0674] Each of plastic pots was filled with soil and thereto wheat (cv; Apogee) seeds were sown and the wheats were grown in a greenhouse for 10 days. Thereafter, the present compound 1, 3 to 6, 10, 11, 13 to 16, 18 to 21, 25, 26, 29 to 37, 39, 40, 46 to 49, 51, 53 to 55, 57, 58, 64, 72, 73, 75, 77 to 80, 82, 83, 85 to 88, or 89, each of which was made to a formulation according to the similar method to that of Formulation Example 6, was mixed with water so as to be 200 ppm. The mixtures were sprayed to foliar parts so as to adhere adequately on the leaves of the above-mentioned wheat. After spraying the mixtures, the wheats were air-dried and after 4 days, an aqueous suspension of the conidia of Septoria tritici was spraying-inoculated. After the inoculation, the wheats were placed at 18° C. under a high humidity for 3 days and then under lighting for 14 to 18 days, and a lesion area was observed. As a result, every of the lesion areas in wheats treated with each of the present compounds showed 30% or less compared to the lesion area in an untreated wheat.

Test Example 16: Control Test Against Septoria Leaf Blotch (Septoria tritici)

[0675] Each of plastic pots was filled with soil and thereto wheat (cv; Apogee) seeds were sown and the wheats were grown in a greenhouse for 10 days. Thereafter, the present compound 3 to 5, 7 to 11, 15, 16, 21, 25, 26, 29, 31, 34, 37, 39, 44, 46, 47, 49, 57, 58, 71 to 75, 77 to 82, 84, 88, 89, or 90, each of which was made to a formulation according to the similar method to that of Formulation Example 6, was mixed with water so as to be 200 ppm. The mixtures were sprayed to foliar parts so as to adhere adequately on the leaves of the above-mentioned wheat. After spraying the mixtures, the wheats were air-dried and were placed under lighting for 14 to 18 days, and a lesion area was observed. As a result, every of the lesion areas in wheats treated with each of the present compounds showed 30% or less compared to the lesion area in an untreated wheat.

Test Example 17: Control Test Against Tomato Late Blight (Phytophthora infestans)

[0676] Each of plastic pots was filled with soils and thereto tomato (cv; PATIO) seeds were sown and the tomatoes were grown in a greenhouse for 20 days. Thereafter, the present compound 2, 11 to 14, 16, 18 to 21, 29, 35, 39, 49, 51, 52, 55, 56, 60 to 64, 66, 76, 80, 85, or 86, each of which was made to a formulation according to the similar method to that of Formulation Example 6, was mixed with water so as to be 200 ppm. The mixtures were sprayed to foliar parts so as to adhere adequately on the leaves of the above-mentioned tomato. After spraying the mixtures, the tomatoes were air-dried and after 1 day, an aqueous suspension of the spores of Phytophthora infestans were spraying-inoculated. After the inoculation, the tomatoes were placed in a greenhouse of 23° C. during daytime and 20° C. during nighttime under a high humidity for 1 day, and a lesion area was observed. As a result, every of the lesion areas in tomatoes treated with each of the present compounds showed 30% or less compared to the lesion area in an untreated tomato.

Test Example 18: Control Test Against Soybean Rust (Phakopsora pachyrhizi)

[0677] Each of plastic pots was filled with soil and thereto soybean (cv: Kurosengoku) seeds were sown and the soybeans were grown in a greenhouse for 10 to 14 days. Thereafter, the present compound 1 to 16, 18 to 23, 25, 26, 29 to 32, 34, 35, 37 to 40, 44 to 46, 48, 49, 51 to 59, 61 to 64, 68, 71 to 73, 75 to 77, 79 to 83, 85 to 89, or 90, each of which was made to a formulation according to the similar method to that of Formulation Example 6, was mixed with water so as to be 200 ppm. The resulting mixtures were sprayed to foliar parts so as to adhere adequately on the leaves of the above-mentioned soybean. After spraying the mixtures, the soybeans were air-dried and after 2 to 5 days, an aqueous suspension of the conidia of Phakopsora pachyrhizi was spraying-inoculated. After the inoculation, the soybeans were placed in a greenhouse of 23° C. during daytime and 20° C. during nighttime under a high humidity for 1 to 2 days, and were then cultivated in the greenhouse for 12 days, and a lesion area was observed. As a result, every of the lesion areas in soybean treated with each of the present compounds showed 30% or less compared to the lesion area in an untreated soybean.

Test Example 19: Control Test Against Soybean Rust (Phakopsora pachyrhizi)

[0678] Each of plastic pots was filled with soil and thereto soybean (cv: Kurosengoku) seeds were sown and the soybeans were grown in a greenhouse for 10 days, and an aqueous suspension containing the conidia of Phakopsora pachyrhizi was spraying-inoculated. After the inoculation, the soybeans were placed in a greenhouse of 23° C. during daytime and 20° C. during nighttime under a high humidity for 1 day, and were then cultivated in the greenhouse for 1 to 2 days, and thereafter, the present compound 1 to 16, 18, 19, 21 to 23, 25, 26, 37, 40, 44, 46, 47 to 49, 57, 58, 68, 71 to 77, 80 to 82, 89, or 90, each of which was made to a formulation according to the similar method to that of Formulation Example 6, was mixed with water so as to be 200 ppm, and the resulting mixtures were sprayed to foliar parts so as to adhere adequately on the leaves of the above-mentioned soybean. After spraying the mixtures, the soybeans were air-dried and cultivated in a greenhouse for 8 days, and a lesion area was then observed. As a result, every of the lesion areas in soybean treated with each of the present compounds showed 30% or less compared to the lesion area in an untreated soybean.

Test Example 20: Control Test Against Soybean Leaf Spot (Cercospora sojina)

[0679] Each of plastic pots was filled with soil and thereto soybean (cv: Tachinagawa) seeds were sown and the soybeans were grown in a greenhouse for 13 days. Thereafter, the present compound 1 to 16, 18 to 21, 25, 26, 29 to 35, 37, 39, 40, 44, 46 to 49, 54 to 58, 64, 71 to 89, or 90, each of which was made to a formulation according to the similar method to that of Formulation Example 6, was mixed with water so as to be 200 ppm. The resulting mixtures were sprayed to foliar parts so as to adhere adequately on the leaves of the above-mentioned soybean. After spraying the mixtures, the soybeans were air-dried and after 1 day, an aqueous suspension of the conidia of Cercospora sojina was spraying-inoculated. After the inoculation, the soybeans were placed in a greenhouse of 23° C. during daytime and 20° C. during nighttime under a high humidity for 3 days, and were then cultivated in the greenhouse for 16 days, and a lesion area was observed. As a result, every of the lesion areas in soybean treated with each of the present compounds showed 30% or less compared to the lesion area in an untreated soybean.

Test Example 21: Control Test Against Tomato Early Blight (Alternaria solani)

[0680] Each of plastic pots was filled with soils and thereto tomato (cv; PATIO) seeds were sown and the tomatoes were grown in a greenhouse for 20 days. Thereafter, the present compound 3 to 6, 9, 11 to 16, 18 to 20, 29, 32, 35, 36, 44, 51, 57 to 59, 68, 71, 75, 76, 80, 86, or 87, each of which was made to a formulation according to the similar method to that of Formulation Example 6, was mixed with water so as to be 200 ppm. The resulting mixtures were sprayed to foliar parts so as to adhere adequately on the leaves of the above-mentioned tomato. After spraying the mixtures, the tomatoes were air-dried and after 1 day, an aqueous suspension of the conidia of Alternaria solani were spraying-inoculated. After the inoculation, the tomatoes were placed at 18° C. under a high humidity for 6 days, and a lesion area was observed. As a result, every of the lesion areas in tomatoes treated with each of the present compounds showed 30% or less compared to the lesion area in an untreated tomato.

Test Example 22: Control Test Against Kidney Bean Stem Rot (Sclerotinia sclerotiorum)

[0681] Each of plastic pots was filled with soil and thereto Kidney bean (cv; NAGAUZURA SAITO) seeds were sown and the kidney beans were grown in a greenhouse for 8 days. Thereafter, the present compound 2 to 16, 18 to 20, 25, 26, 29, 48, 53, 55, 57, 58, 64, 71, 76, 77, or 89, each of which was made to a formulation according to the similar method to that of Formulation Example 6, was mixed with water so as to be 200 ppm. The resulting mixtures were sprayed to the foliar parts so as to adhere adequately on the leaves of the above-mentioned kidney bean. After spraying the mixtures, the kidney beans were air-dried and a PDA medium containing hyphae of Sclerotinia sclerotiorum was placed on the leaves of the kidney bean. After the inoculation, all kidney beans were placed under a high humidity during only night and after 4 days, a lesion area was observed. As a result, every of the lesion areas in kidney beans treated with each of the present compounds showed 30% or less compared to the lesion area in an untreated kidney beans.

[0682] Next, it is shown that the present compound is useful for control on harmful arthropod.

Test Method 23

[0683] The present compound is made to a formulation according to a similar method to that described in the Formulation Example 6, and thereto is added water containing 0.03 v/v % of a spreader to prepare a diluted solution containing a prescribed concentration of the test compound.

[0684] Cabbage (Brassicae oleracea) seedling (on the developmental stage of the second to third true leaf) is planted in a cup, and the diluted solutions are sprayed into the seedling at a ratio of 20 mL/seedling. Thereafter, the stem and leaf of the seedling is cut out and is then installed into the container that is covered with the filter paper. Five (5) cabbage moth (Plutella xylostella) at the second instar larval stages are released into the cup. After 5 days, the surviving insects are counted, and the mortality of insects is calculated by the following equation.

Mortality (%)={1−the number of the surviving insects/5}×100

Test Example 23

[0685] The test was conducted at the prescribed concentration of 500 ppm by using the present compound 28 according to the Test method 23, and as a result, the present compound 28 showed 100% as a mortality.

INDUSTRIAL APPLICABILITY

[0686] The compound of the present invention has efficacies on controlling pests, and can be used to control pests.