Sulfonylaminobenzamide compound and pest control agent

Abstract

A compound represented by formula (I) or a salt thereof. ##STR00001## In formula (I), R.sup.1 and R.sup.4 each independently represent a hydrogen atom, or an unsubstituted or substituted C1 to C6 alkyl group or the like. R.sup.2 represents a hydrogen atom, or an unsubstituted or substituted C1 to C6 alkyl group or the like. R.sup.3 represents an unsubstituted or substituted C1 to C6 alkyl group or the like. R.sup.5 represents a C1 to C6 haloalkyl group or the like. G represents an oxygen atom or a sulfur atom. R.sup.6 and R.sup.7 each independently represent a hydrogen atom, or an unsubstituted or substituted C1 to C6 alkyl group or the like. n represents 0 or 1. R.sup.8 and R.sup.9 each independently represent a hydrogen atom, or an unsubstituted or substituted C1 to C6 alkyl group. Ar represents an unsubstituted or substituted C6 to C10 aryl group or the like.

Claims

1. A compound represented by formula (I) or a salt thereof: ##STR00011## wherein in formula (I): R.sup.1, R.sup.2, R.sup.4, R.sup.6 and R.sup.7 each independently represent a hydrogen atom; R.sup.3 represents a substituted C1 to C6 alkyl group; R.sup.5 represents a trifluoromethyl group; G represents an oxygen atom or a sulfur atom; n represents 0 or 1; R.sup.8 and R.sup.9 each independently represent a hydrogen atom, or an unsubstituted or substituted C1 to C6 alkyl group; and Ar represents an unsubstituted or substituted C6 to C10 aryl group, wherein the substituent on the C6 to C10 aryl group for Ar is selected from the group consisting of halogeno group, C1 to C6 alkyl group, C1 to C6 haloalkyl group, C1 to C6 alkoxy group, C1 to C6 haloalkoxy group, a carboxyl group, C1 to C6 alkylcarbonyl group, C1 to C6 alkylcarbonylamino group, C1 to C6 alkoxycarbonyl group, unsubstituted or C1 to C6 alkyl-substituted 5-membered heteroaryl group, a 4,5-dihydrooxazol-2-yl group, 6-membered heteroaryl group, C1 to C6 alkoxyimino C1 to C6 alkyl group, a cyano group, a nitro group, and a pentafluorosulfanyl group.

2. A pest control agent comprising at least one substance selected from the group consisting of the compound according to claim 1 and salts thereof as an active constituent.

3. A nematicide comprising at least one substance selected from the group consisting of the compound according to claim 1 and salts thereof as an active constituent.

Description

EXAMPLES

(1) [Formulations]

(2) Several examples of formulations of the pest control agent, insecticide, miticide, nematicide, endoparasite control agent or parasiticide of the present invention are described below, but the additives and the addition ratios are not limited to those detailed in these examples, and can be modified over a wide range. The units parts in the formulations indicate parts by weight.

(3) Formulations for agricultural and horticultural use and formulations for paddy rice are described below.

(4) (Formulation 1: Water-Dispersible Powder)

(5) Forty parts of the sufonylaminobenzamide compound of the present invention, 53 parts of diatomaceous earth, 4 parts of a higher alcohol sulfate and 3 parts of an alkylnaphthalene sulfonate salt were mixed together uniformly and then finely crushed to obtain a water-dispersible powder containing 40% of the active constituent.

(6) (Formulation 2: Emulsion)

(7) Thirty parts of the sufonylaminobenzamide compound of the present invention, 33 parts of xylene, 30 parts of dimethylformamide and 7 parts of a polyoxyethylene alkyl aryl ether were mixed together and dissolved to obtain an emulsion containing 30% of the active constituent.

(8) (Formulation 3: Granules)

(9) Five parts of the sufonylamninobenzamide compound of the present invention, 40 parts of talc, 38 parts of clay, 10 parts of bentonite and 7 parts of sodium alkyl sulfate were mixed together uniformly and then finely crushed, and the resulting powder was granulated into a granular shape having a diameter of 0.5 to 1.0 mm to obtain granules containing 5% of the active constituent.

(10) (Formulation 4: Granules)

(11) Five parts of the sufonylaminobenzamide compound of the present invention, 73 parts of clay, 20 parts of bentonite, 1 part of sodium dioctylsulfosuccinate and 1 part of potassium phosphate were thoroughly crushed and mixed together, water was then added to the resulting powder and thoroughly mixed, and the mixture was granulated and dried to obtain granules containing 5% of the active constituent.

(12) (Formulation 5: Suspension)

(13) Ten parts of the sufonylaminobenzamide compound of the present invention, 4 parts of a polyoxyethylene alkyl aryl ether, 2 parts of sodium polycarboxylate, 10 parts of glycerol, 0.2 parts of xanthan gum and 73.8 parts of water were mixed, and the resulting mixture was subjected to wet crushing down to a grain size of not more than 3 microns to obtain a suspension containing 10% of the active constituent.

(14) Formulations for endoparasite control and formulations for parasiticides are described below.

(15) (Formulation 6: Granulated Powder)

(16) Five parts of the sufonylaminobenzamide compound of the present invention was dissolved in an organic solvent to obtain a solution, the solution was sprayed onto 94 parts of kaolin and 1 part of white carbon, and the solvent was then evaporated under reduced pressure. This type of granulated powder can be mixed with animal feed.

(17) (Formulation 7: Injection)

(18) From 0.1 to 1 part of the sufonylaminobenzamide compound of the present invention and 99 to 99.9 parts of peanut oil were mixed together uniformly, and the resulting mixture was then filter-sterilized using a sterilizing filter.

(19) (Formulation 8: Pour-on Agent)

(20) Five parts of the sufonylaminobenzamide compound of the present invention, 10 parts of a myristate ester and 85 parts of isopropanol were mixed together uniformly to obtain a pour-on agent.

(21) (Formulation 9: Spot-on Agent)

(22) From 10 to 15 parts of the sufonylaminobenzamide compound of the present invention, 10 parts of a palmitate ester and 75 to 80 parts of isopropanol were mixed together uniformly to obtain a spot-on agent.

(23) (Formulation 10: Spray-on Agent)

(24) One part of the sufonylaminobenzamide compound of the present invention, 10 parts of propylene glycol and 89 parts of isopropanol were mixed together uniformly to obtain a spray-on agent.

(25) Examples of the compound are described below in order to describe the present invention in more detail. However, the present invention is in no way limited by the example compounds presented below.

Example 1

Synthesis of 4-(trifluoromethyl)-N-[4-(trifluoromethyl)phenyl]-2-(trifluoromethylsulfonylamino)benzamide (Compound Number: a-9)

Step 1

Synthesis of methyl 2-amino-4-(trifluoromethyl)benzoate

(26) ##STR00005##

(27) First, 4.10 g of 2-amino-4-(trifluoromethyl)benzoic acid was dissolved in 70 ml of methanol, and 12 ml of thionyl chloride was then added dropwise to the solution at 0 C. The temperature was then raised, and the reaction mixture was stirred for 12 hours under reflux conditions. After cooling to room temperature, the reaction solution was concentrated under reduced pressure, and the residue was dissolved in water and ethyl acetate. The resulting organic phase was washed with a saturated solution of sodium bicarbonate, dried over anhydrous magnesium sulfate, and then filtered. The filtrate was then concentrated under reduced pressure to obtain 3.70 g (yield: 85%) of the target product.

(28) The .sup.1H-NMR of the obtained target product is shown below.

(29) .sup.1H-NMR (400 MHz, CDCl.sub.3): 7.94 (d, 1H), 6.89 (s, 1H), 6.83 (d, 1H), 5.90 (brs, 2H), 3.89 (s, 3H).

Step 2

Synthesis of methyl 4-(trifluoromethyl)-2-(trifluoromethyl sulfonylamino)benzoate

(30) ##STR00006##

(31) First, 4.92 g of methyl 2-amino-4-(trifluoromethyl)benzoate and 4.55 g of triethylamine were dissolved in 75 ml of chloroform, and 12.7 g of trifluoromethanesulfonic anhydride was then added dropwise to the solution at 0 C. The temperature was then raised to room temperature, and the reaction solution was stirred for 7 hours. The reaction solution was then poured into water and extracted with chloroform. The thus obtained organic phase was washed with a saturated solution of sodium bicarbonate, dried over anhydrous magnesium sulfate, and then filtered. The filtrate was then concentrated under reduced pressure, and the obtained residue was purified by silica gel column chromatography to obtain 5.80 g (yield: 74%) of the target product.

(32) The .sup.1H-NMR of the obtained target product is shown below.

(33) .sup.1H-NMR (400 MHz, CDCl.sub.3): 11.37 (s, 1H), 8.19 (d, 1H), 8.02 (s, 1H), 7.46 (d, 1H), 3.98 (s, 3H).

Step 3

Synthesis of 4-(trifluoromethyl)-2-(trifluoromethylsulfonylamino)benzoic acid

(34) ##STR00007##

(35) First, 5.80 g of methyl 4-(trifluoromethyl)-2-(trifluoromethylsulfonylamino)benzoate was dissolved in 30 ml of tetrahydrofuran, and 13 ml of a 4N aqueous solution of sodium hydroxide was added at room temperature. The temperature was then raised to 80 C., and the reaction solution was stirred for 2 hours. After cooling to room temperature, the reaction solution was poured into water, and diethyl ether was added to achieve a phase separation. Dilute hydrochloric acid was added to the obtained aqueous phase under cooling to produce an acidic state, and an extraction was then performed with ethyl acetate. The thus obtained organic phase was washed with a saturated saline solution, dried over anhydrous magnesium sulfate, and then filtered. The filtrate was then concentrated under reduced pressure to obtain 4.56 g (yield: 82%) of the target product.

(36) The .sup.1H-NMR of the obtained target product is shown below.

(37) .sup.1H-NMR (400 MHz, DMSO-d.sub.6): 8.08 (d, 1H), 7.85 (s, 1H), 7.40 (d, 1H)

Step 4

Synthesis of 4-(trifluoromethyl)-N-[4-(trifluoromethyl)phenyl]-2-(trifluoromethylsulfonylamino)benzamide

(38) ##STR00008##

(39) First, 0.40 g of 4-(trifluoromethyl)-2-(trifluoromethylsulfonylamino)benzoic acid was dissolved in 4 ml of thionyl chloride, and the solution was stirred for 2 hours under reflux conditions. The reaction solution was then concentrated under reduced pressure, and the residue was dissolved in 15 ml of chloroform. Subsequently, 0.23 g of 4-trifluoromethylaniline was added at 0 C., and 0.30 g of sodium bicarbonate was then added. The temperature as then raised to room temperature, and the reaction mixture was stirred for 3 hours. The reaction mixture was then concentrated under reduced pressure, and the residue was dissolved in water and ethyl acetate. The thus obtained organic phase was washed with a saturated saline solution, dried over anhydrous magnesium sulfate, and then filtered. The filtrate was then concentrated under reduced pressure, and the obtained residue was purified by silica gel column chromatography to obtain 0.44 g (yield: 77%) of the target product.

(40) The .sup.1H-NMR of the obtained target product is shown below.

(41) .sup.1H-NMR (400 MHz, DMSO-d.sub.6): 13.50 (s, 1H), 8.21 (d, 1H), 7.86 (s, 1H), 7.81 (d, 2H), 7.71 (d, 2H), 7.23 (d, 1H).

(42) A part of compounds of the present invention produced using a similar method to the example described above are shown in Table 1 to Table 2. Table 1 shows the substituents in compounds represented by formula (I-1). Table 2 shows the substituents in compounds represented by formula (I-2). The physical state or melting point (m.p.) is also shown in the tables to indicate the physical property of each compound. In the tables, Me represents a methyl group, Et represents an ethyl group, and .sup.iPr represents an isopropyl group.

(43) ##STR00009##

(44) TABLE-US-00001 TABLE 1 Compound number R.sup.1 R.sup.2 R.sup.3 R.sup.4 R.sup.5 R.sup.6 R.sup.7 G Ar Physical property a-1 H H Cl H CF.sub.3 H H O 3,5-(CF.sub.3).sub.2-phenyl amorphous a-2 H H CF.sub.3 H CF.sub.3 H H O 3-CF.sub.3-4-F-phenyl m.p. 187-189 C. a-3 H H CF.sub.3 H CF.sub.3 H H O 3,5-(CF.sub.3).sub.2-phenyl amorphous a-4 H H CF.sub.3 H CF.sub.3 H H O 4-CF.sub.3-phenyl m.p. 212-214 C. a-5 H H Cl H CF.sub.3 H Me O 3,5-(CF.sub.3).sub.2-phenyl m.p. 148-150 C. a-6 H H F H CF.sub.3 H H O 3,5-(CF.sub.3).sub.2-phenyl amorphous a-7 H H CF.sub.3 H CF.sub.3 H H O 2-Cl-4-CF.sub.3-phenyl m.p. 180-182 C. a-8 H H CF.sub.3 H CF.sub.3 H H O 5-CF.sub.3-pyridin-2-yl m.p. 220 C. up a-9 H H CF.sub.3 H CF.sub.3 H H O 3-F-5-CF.sub.3-phenyl m.p. 179-181 C. a-10 H H CF.sub.3 H CF.sub.3 H H O 3-Cl-4-CF.sub.3-phenyl m.p. 203-205 C. a-11 H H CF.sub.3 H CF.sub.3 H H O 2-F-5-CF.sub.3-phenyl m.p. 172-174 C. a-12 H H CF.sub.3 H CF.sub.3 H H O 3-OCF.sub.3-phenyl amorphous a-13 H H CF.sub.3 H CF.sub.3 H H O 4-Me-phenyl m.p. 192-194 C. a-14 H H CF.sub.3 H CF.sub.3 H H O 4-Cl-phenyl m.p. 198-200 C. a-15 H H CF.sub.3 H CF.sub.3 H H O 4-OCF.sub.3-phenyl amorphous a-16 H F F H CF.sub.3 H H O 3-CF.sub.3-4-F-phenyl m.p. 172-174 C. a-17 H H Me H CF.sub.3 H H O 3-CF.sub.3-4-F-phenyl m.p. 176-178 C. a-18 H H CF.sub.3 H CF.sub.3 H H O 2,6-Cl.sub.2-4-CF.sub.3-phenyl m.p. 194-195 C. a-19 H H CF.sub.3 H CF.sub.3 H H O 5-(1,1,1,3,3,3- m.p. 220 C. up hexafluoropropan-2- yl)thiazol-2-yl a-20 H H CF.sub.3 H CF.sub.3 H H O 2-Me-4- m.p. 188-190 C. (perfluoropropan-2-yl)- phenyl a-21 H H CF.sub.3 H CF.sub.3 Me H O 3-CF.sub.3-4-F-phenyl m.p. 178-179 C. a-22 H H CF.sub.3 H CF.sub.3 H H O 3,4-Cl.sub.2-phenyl m.p. 193-195 C. a-23 H H CF.sub.3 H CF.sub.3 H H O 3-Cl-5-CF.sub.3-pyridin-2-yl m.p. 220 C. up a-24 H H OCF.sub.3 H CF.sub.3 H H O 4-OCF.sub.3-phenyl m.p. 172-175 C. a-25 H H OCF.sub.3 H CF.sub.3 H H O 3-CF.sub.3-4-F-phenyl m.p. 165-168 C. a-26 H H OCF.sub.3 H CF.sub.3 H H O 4-CF.sub.3-phenyl m.p. 176-179 C. a-27 H H CF.sub.3 H CF.sub.3 Me H O 4-OCF.sub.3-phenyl m.p. 167-168 C. a-28 H H CF.sub.3 H CF.sub.3 H H O 4-SF.sub.5-phenyl m.p. 220-222 C. a-29 H H Br H CF.sub.3 H H O 4-OCF.sub.3-phenyl amorphous a-30 H H CF.sub.3 H CH.sub.2CF.sub.3 H H O 4-OCF.sub.3-phenyl m.p. 185-188 C. a-31 H H 1H-1,2,4-triazol-1- H CF.sub.3 H H O 4-OCF.sub.3-phenyl m.p. 220 C. up yl a-32 H H 6-Cl-pyridin-3-yl H CF.sub.3 H H O 4-OCF.sub.3-phenyl m.p. 199-201 C. a-33 H H CF.sub.3 H CHF.sub.2 H H O 4-OCF.sub.3-phenyl m.p. 127-129 C. a-34 H H 6-CF.sub.3-pyridin-3-yl H CF.sub.3 H H O 4-OCF.sub.3-phenyl m.p. 170-172 C. a-35 H H 4-CF.sub.3-phenyl H CF.sub.3 H H O 4-OCF.sub.3-phenyl m.p. 152-154 C. a-36 H H CN H CF.sub.3 H H O 4-CF.sub.3-phenyl amorphous a-37 H H CF.sub.3 H CF.sub.3 H H O 3-CF.sub.3-4-CN-phenyl m.p. 220 C. up a-38 H H CN H CH.sub.2CF.sub.3 H H O 4-CF.sub.3-phenyl m.p. 220 C. up a-39 H H CF.sub.3 H CF.sub.3 H H O 4-CN-phenyl m.p. 220 C. up a-40 H H CN H CF.sub.3 H H O 4-CN-phenyl m.p. 220 C. up a-41 H H Cl H CF.sub.3 H H O 3-CF.sub.3-4-F-phenyl amorphous a-42 H H 2-Cl-4-CF.sub.3-phenyl H CF.sub.3 H H O 4-OCF.sub.3-phenyl amorphous a-43 H H CF.sub.3 H CF.sub.3 H H O 4-SCF.sub.3-phenyl m.p. 185-187 C. a-44 H H CF.sub.3 H CF.sub.3 H H O 3-(1H-1,2,4-triazol-1-yl)phenyl m.p. 220 C. up a-45 H H CF.sub.3 H CF.sub.3 H H O 4-(3-Me-1,2,4-oxadiazol- m.p. 220 C. up 5-yl)phenyl a-46 H H CF.sub.3 H CF.sub.3 H H O 4-(5-Me-1,3,4-oxadiazol- m.p. 220 C. up 2-yl)phenyl a-47 H H CF.sub.3 H CF.sub.3 H H O pyridin-3-yl m.p. 220 C. up a-48 H H CF.sub.3 H CF.sub.3 H H O pyridin-4-yl m.p. 220 C. up a-49 H H CF.sub.3 H CF.sub.3 H H O 2-COOMe-4-Br-phenyl m.p. 220 C. up a-50 H H CF.sub.3 H CF.sub.3 H H O 4-NO.sub.2-phenyl m.p. 220 C. up a-51 H H CF.sub.3 H CF.sub.3 H H O 2-CN-4-Cl-phenyl m.p. 230 C. up a-52 H H CF.sub.3 H CF.sub.3 H H O 2-CONHMe-4-Cl-phenyl m.p. 230 C. up a-53 H H CF.sub.3 H CF.sub.3 H H O 2-F-4-CN-phenyl m.p. 230 C. up a-54 H H CF.sub.3 H CF.sub.3 H H O 2-F-4-CF.sub.3-phenyl amorphous a-55 H H CF.sub.3 H CF.sub.3 H H O 2-CF.sub.3-4-Cl-phenyl amorphous a-56 H H CF.sub.3 H CF.sub.3 H H O 2-OCH.sub.2CF.sub.3-pyridin-4-yl amorphous a-57 H H CF.sub.3 H CF.sub.3 H H O 2-COOMe-4-F-phenyl m.p. 135-137 C. a-58 H H CF.sub.3 H CF.sub.3 H H O 2-COOMe-4-CF.sub.3-phenyl m.p. 127-130 C. a-59 H H CF.sub.3 H CF.sub.3 H H O 2-OEt-4-CF.sub.3-phenyl m.p. 220 C. up a-60 H H CF.sub.3 H CF.sub.3 H H O 2-COOMe-4-Cl-phenyl m.p. 220 C. up a-61 H H CF.sub.3 H CF.sub.3 H H O 2-COOEt-4-Br-phenyl m.p. 195-197 C. a-62 H H CF.sub.3 H CF.sub.3 H H O 2-COOMe-4-I-phenyl m.p. 220 C. up a-63 H H CF.sub.3 H CF.sub.3 H H O 2-COOMe-5-CF.sub.3-phenyl m.p. 132-134 C. a-64 H H CF.sub.3 H CF.sub.3 H H O 3-F-4-CF.sub.3-phenyl amorphous a-65 H H CF.sub.3 H CF.sub.3 H H O 2-COO.sup.iPr-4-Br-phenyl m.p. 142-144 C. a-66 H H CF.sub.3 H CF.sub.3 H H O 2-COEt-4-CF.sub.3-phenyl m.p. 105-107 C. a-67 H H CF.sub.3 H CF.sub.3 H H O 2-COOMe-4-CN-phenyl m.p. 218-220 C. a-68 H H CF.sub.3 H CF.sub.3 H H O 2-Cl-4-Br-phenyl m.p. 181-183 C. a-69 H H CF.sub.3 H CF.sub.3 H H O 3-Cl-4-Br-phenyl amorphous a-70 H H CF.sub.3 H CF.sub.3 H H O 3-CF.sub.3-4-Cl-phenyl amorphous a-71 H H CF.sub.3 H CF.sub.3 H H O 2-COOMe-4,6-Cl.sub.2-phenyl amorphous a-72 H H CF.sub.3 H CF.sub.3 H H O 3-COOMe-4-Cl-phenyl m.p. 217-219 C. a-73 H H Br H CF.sub.3 H H O 2-COOMe-4-Br-phenyl m.p. 171-173 C. a-74 H H CF.sub.3 H CF.sub.3 H H O 4-Br-2-(4,5-dihydrooxazol-2-yl)- m.p. 220 C. up phenyl a-75 H H CF.sub.3 H CF.sub.3 H H O 2-COOMe-4-NO.sub.2-phenyl m.p. 174-176 C. a-76 H H CF.sub.3 H CF.sub.3 H H O 4-Br-2-(1H-pyrazol-1-yl)-phenyl m.p. 151-153 C. a-77 H H CF.sub.3 H CF.sub.3 H H O 2-SO.sub.2Me-4-Br-phenyl m.p. 215-217 C. a-78 H H CF.sub.3 H CF.sub.3 H H O 2-COOMe-4,5-F.sub.2-phenyl m.p. 177-180 C. a-79 H H CF.sub.3 H CF.sub.3 H H O 2-COOMe-4-I-5-Cl- m.p. 170-172 C. phenyl a-80 H H CF.sub.3 H CF.sub.3 H H O 2-COOMe-4,5-Cl.sub.2-phenyl m.p. 154-156 C. a-81 H H CF.sub.3 H CF.sub.3 H H O 5-CF.sub.3-2-(1H-pyrazol-1- m.p. 164-167 C. yl)-phenyl a-82 H H CF.sub.3 H CF.sub.3 H H O 2-COOMe-4-CF.sub.3-5-Cl- m.p. 172-174 C. phenyl a-83 H H CF.sub.3 H CF.sub.3 H H O 2-COOMe-4-Br-5-Cl-phenyl m.p. 163-165 C. a-84 H CF.sub.3 Cl H CF.sub.3 H H O 2-COOMe-4-Br-phenyl m.p. 220 C. up a-85 H H CF.sub.3 H CF.sub.3 H H O 2-COOMe-4-Br-5-F-phenyl m.p. 163-165 C. a-86 H H CF.sub.3 H CF.sub.3 H H O 2-COOMe-4-CF.sub.3-5-F- m.p. 170-172 C. phenyl a-87 H F F H CF.sub.3 H H O 2-COOMe-4,5-F.sub.2-phenyl m.p. 220 C. up a-88 H Br Cl H CF.sub.3 H H O 2-COOMe-4,5-F.sub.2-phenyl m.p. 220 C. up a-89 H H CF.sub.3 H CF.sub.3 H H O 2-COOMe-5-NO.sub.2-phenyl m.p. 163-165 C. a-90 H H CF.sub.3 H CF.sub.3 H H O 2-COOMe-4-Cl-5-F- m.p. 220 C. up phenyl a-91 H H NO.sub.2 H CF.sub.3 H H O 2-COOMe-4,5-F.sub.2-phenyl m.p. 220-222 C. a-92 H H CF.sub.3 H CF.sub.3 H H O 2-COOMe-5-Cl-phenyl m.p. 131-133 C. a-93 H F F H CF.sub.3 H H O 2-COOMe-5-CF.sub.3-phenyl m.p. 125-128 C. a-94 H H CF.sub.3 H CF.sub.3 H H O 2-COOMe-5-F-phenyl m.p. 198-200 C. a-95 H H CF.sub.3 H CF.sub.3 H H O 6-Cl-4-COOMe-pyridin-3-yl m.p. 168-170 C. a-96 H H CF.sub.3 H CF.sub.3 H H O 2-Cl-5-COOMe-pyridin-4-yl m.p. 183-185 C. a-97 H Cl Cl H CF.sub.3 H H O 2-COOMe-4,5-F.sub.2-phenyl m.p. 220 C. up a-98 H F CF.sub.3 H CF.sub.3 H H O 2-COOMe-4,5-F.sub.2-phenyl m.p. 220 C. up a-99 H CF.sub.3 F H CF.sub.3 H H O 2-COOMe-4,5-F.sub.2-phenyl m.p. 220 C. up a-100 H H 6-CF.sub.3-pyridin- H CF.sub.3 H H O 2-COOMe-4,5-F.sub.2-phenyl m.p. 195-197 C. 3-yl a-101 H H CF.sub.3 H CF.sub.3 H H O 5-CF.sub.3-2-(1H-1,2,4- m.p. 220 C. up triazol-1-yl)-phenyl a-102 H H CF.sub.3 H CF.sub.3 H H O 2-COOMe-4-Br-6-F- m.p. 178-180 C. phenyl a-103 H H CF.sub.3 H CF.sub.3 H H O 2-NO.sub.2-4-CF.sub.3-phenyl m.p. 177-179 C. a-104 H H CF.sub.3 H CF.sub.3 H H O 2-COOMe-3-Cl-phenyl m.p. 181-184 C. a-105 H H CF.sub.3 H CF.sub.3 H H O 2-COOMe-4,6-F.sub.2-phenyl m.p. 152-154 C. a-106 H H CF.sub.3 H CF.sub.3 H H O 2-COOMe-4,5,6-F.sub.3-phenyl m.p. 160-162 C. a-107 H H CF.sub.3 H CF.sub.3 H H O 2-COOMe-3,4,5,6-F.sub.4- m.p. 182-184 C. phenyl a-108 H H CF.sub.3 H CF.sub.3 H H O 2-NO.sub.2-4,5-F.sub.2-phenyl m.p. 158-161 C. a-109 H H CF.sub.3 H CF.sub.3 H H O 2-COOMe-4-OCF.sub.3-phenyl m.p. 210-212 C. a-110 H F F H CF.sub.3 H H O 2-COOMe-4-OCF.sub.3-phenyl m.p. 127-129 C. a-111 H F F H CF.sub.3 H H O 2-COOMe-4-CF.sub.3-phenyl m.p. 128-130 C. a-112 H Br Cl H CF.sub.3 H H O 2-COOMe-4-CF.sub.3-phenyl m.p. 220 C. up a-113 H F F H CF.sub.3 H H O 2-COOMe-4-NO.sub.2-phenyl m.p. 220 C. up a-114 H H CF.sub.3 H CF.sub.3 H H O 2-COOMe-3-Cl-4-Br- m.p. 208-210 C. phenyl a-115 H H CF.sub.3 H CF.sub.3 H H O 2-(CHNOMe)-4-Cl-phenyl m.p. 220 C. up a-116 H H CF.sub.3 H CF.sub.3 H H O 2,4,5-F.sub.3-phenyl m.p. 185-187 C. a-117 H H Cl H CF.sub.3 H H O 2-COOMe-4,5-F.sub.2-phenyl m.p. 156-158 C. a-118 H H 6-CF.sub.3-pyridin- H CF.sub.3 H H O 4-CF.sub.3-phenyl m.p. 220-223 C. 3-yl a-119 H H 6-CF.sub.3-pyridin- H CF.sub.3 H H O 3-F-4-CF.sub.3-phenyl m.p. 220 C. up 3-yl a-120 H H 6-CF.sub.3-pyridin- H CF.sub.3 H H O 3-CF.sub.3-4-F-phenyl m.p. 213-215 C. 3-yl a-121 H H 6-CF.sub.3-pyridin- H CF.sub.3 H H O 4-NO.sub.2-phenyl m.p. 220 C. up 3-yl a-122 H CF.sub.3 F H CF.sub.3 H H O 4-CF.sub.3-phenyl m.p. 220 C. up a-123 H F CF.sub.3 H CF.sub.3 H H O 4-CF.sub.3-phenyl amorphous a-124 H Br Cl H CF.sub.3 H H O 4-CF.sub.3-phenyl m.p. 220 C. up a-125 H H CF.sub.3 H CF.sub.3 H H O 3-COOMe-thiophen- m.p. 210-213 C. 2-yl a-126 H H CF.sub.3 H CF.sub.3 H H O 2-COOMe-3-F-4-Br-phenyl m.p. 185-187 C. a-127 H F F H CF.sub.3 H H O 4-CF.sub.3-phenyl amorphous a-128 H Cl Cl H CF.sub.3 H H O 4-CF.sub.3-phenyl amorphous a-129 H Cl F H CF.sub.3 H H O 4-CF.sub.3-phenyl amorphous a-130 H H CF.sub.3 H CF.sub.3 H H O 2-NHCOMe-5-CF.sub.3-phenyl m.p. 220 C. up a-131 H Br Cl H CF.sub.3 H H O 2-COOMe-5-CF.sub.3-phenyl m.p. 160-162 C. a-132 H Cl Br H CF.sub.3 H H O 2-COOMe-4,5-F.sub.2-phenyl m.p. 220 C. up a-133 H H CF.sub.3 H CF.sub.3 H H O 2-COMe-4-Br-phenyl m.p. 151-153 C. a-134 H H CF.sub.3 H CF.sub.3 H H O 2-COMe-5-CF.sub.3-phenyl m.p. 113-115 C. a-135 H H CF.sub.3 H CF.sub.3 H H O 2-(1H-pyrazol-1-yl)-4- m.p. 223-225 C. CF.sub.3-phenyl a-136 H Br Cl H CF.sub.3 H H O 2-(1H-pyrazol-1-yl)-5- m.p. 199-202 C. CF.sub.3-phenyl a-137 H Cl F H CF.sub.3 H H O 2-COOMe-5-CF.sub.3-phenyl m.p. 150-152 C. a-138 H H CF.sub.3 H CF.sub.3 H H O 3,4-F.sub.2-phenyl amorphous a-139 H H CF.sub.3 H CF.sub.3 H H O 2-(1,3,4-oxadiazol-2- m.p. 180-182 C. yl)-5-CF.sub.3-phenyl a-140 H H CF.sub.3 H CF.sub.3 H H O 2-(4,5-dihydrooxazol- m.p. 222-225 C. 2-yl)-5-CF.sub.3-phenyl a-141 H H Cl H CF.sub.2CF.sub.2CF.sub.2CF.sub.3 H H O 3-CF.sub.3-4-F-phenyl amorphous a-142 H H CF.sub.3 H CF.sub.2CF.sub.2CF.sub.2CF.sub.3 H H O 4-OCF.sub.3-phenyl amorphous a-143 H Br Cl H CF.sub.3 H H O 3,4-F.sub.2-phenyl m.p. 227-229 C.

(45) ##STR00010##

(46) TABLE-US-00002 TABLE 2 Compound Physical number R.sup.1 R.sup.2 R.sup.3 R.sup.4 R.sup.5 R.sup.6 R.sup.7 R.sup.8 R.sup.9 G Ar property b-1 H H CF.sub.3 H CF.sub.3 H H H H O 4-Cl-phenyl m.p. 127-129 C. b-2 H H CF.sub.3 H CF.sub.3 H H Me Me O 4-Cl-phenyl amorphous b-3 H H CF.sub.3 H CF.sub.3 H H .sup.iPr H O 4-Cl-phenyl m.p. 168-170 C. b-4 H H CF.sub.3 H CF.sub.3 H H Me H O 3-Cl-5-CF.sub.3-pyridin-2-yl amorphous b-5 H H CF.sub.3 H CF.sub.3 H H Me H O 5-CF.sub.3-pyridin-2-yl m.p. 163-165 C. b-6 H H CF.sub.3 H CF.sub.3 H H Et H O 5-CF.sub.3-pyridin-2-yl amorphous

(47) Among the compounds shown in Table 1 to Table 2, those compounds having a physical property described as viscous oil or amorphous were subjected to a .sup.1H-NMR (DMSO-d.sub.6) measurement. The measurement results are shown in Table 3.

(48) TABLE-US-00003 TABLE 3 Compound number .sup.1H-NMR (DMSO-d.sub.6, ppm) a-1 8.80 (brs, 1H), 8.19 (s, 2H), 8.02 (d, 1H), 7.75 (s, 1H), 7.53 (s, 1H), 7.00 (d, 1H) a-3 8.21 (s, 2H), 8.18 (d, 1H), 7.82 (s, 1H), 7.77 (s, 1H), 7.24 (d, 1H) a-6 8.80 (brs, 1H), 8.19 (s, 2H), 8.08 (m, 1H), 7.73 (s, 1H), 7.25 (d, 1H), 6.78 (m, 1H) a-12 8.20 (d, 1H), 7.90 (s, 1H), 7.85 (s, 1H), 7.48 (t, 1H), 7.37 (d, 1H), 7.22 (d, 1H), 7.05 (d, 1H) a-15 8.21 (d, 1H), 7.85 (s, 1H), 7.72 (d, 2H), 7.36 (d, 2H), 7.22 (d, 1H) a-29 7.94 (d, 1H), 7.69 (m, 3H), 7.34 (d, 2H), 7.11 (d, 1H) a-36 13.40 (s, 1H), 8.77 (bs, 1H), 8.17 (d, 1H), 7.83 (m, 3H), 7.79 (d, 2H), 7.33 (d, 1H) a-41 13.40 (s, 1H), 8.21 (m, 1H), 8.02 (d, 1 H), 7.65 (m, 1H), 7.51 (m, 2H), 6.97 (d, 1 H) a-42 13.20 (bs, 1H), 8.10 (d, 1H), 7.95 (s, 1H), 7.77 (m, 3H), 7.60 (d, 2H), 7.37 (d, 2H), 7.07 (d, 1H) a-54 8.71 (t, 1H), 8.24 (d, 1H), 7.97 (s, 1H), 7.73 (d, 2H), 7.56 (d, 1H), 7.22 (d, 1H) a-55 8.20 (d, 1H), 7.98 (d, 1H), 7.90 (s, 1H), 7.74 (m, 2H), 7.19 (d, 1H) a-56 13.20 (s, 1H), 8.18 (d, 1H), 8.09 (d, 1H), 7.85 (s, 1H), 7.27 (m, 2H), 7.09 (d, 1H), 4.95 (m, 2H) a-64 8.20 (d, 1H), 7.93 (d, 1H), 7.85 (s, 1H), 7.77 (t, 1H), 7.31 (d, 1H), 7.23 (d, 1H) a-69 8.18 (d, 1H), 8.08 (d, 1H), 7.84 (s, 1H), 7.73 (d, 1H), 7.32 (m, 1H), 7.21 (d, 1H) a-70 8.31 (s, 1H), 8.19 (d, 1H), 7.84 (s, 1H), 7.71 (m, 2H), 7.23 (d, 1H) a-71 8.14 (d, 1H), 7.96 (s, 1H), 7.91 (d, 1H), 7.62 (d, 1H), 7.18 (m, 1H) a-123 13.51 (s, 1H), 7.93 (d, 1H), 7.86 (d, 1H), 7.80 (d, 2H), 7.72 (d, 2H) a-127 13.49 (s, 1H), 7.93 (d, 1H), 7.77 (d, 2H), 7.70 (d, 2H), 7.54 (m, 1H) a-128 13.33 (s, 1H), 8.11 (s, 1H), 7.78 (d, 2H), 7.20 (m, 3H) a-129 13.35 (s, 1H), 8.10 (d, 1H), 7.76 (d, 2H), 7.71 (d, 2H), 7.43 (d, 1H) a-138 13.39 (s, 1H), 8.19 (d, 1H), 7.91 (m, 1H), 7.83 (s, 1H), 7.43 (m, 1H), 7.21 (d, 1H), 7.14 (m, 1 H) a-141 13.38 (s, 1H), 8.17 (m, 1H), 8.01 (d, 1H), 7.65 (m, 1H), 7.61 (s, 1H), 7.53 (t, 1H), 7.97 (d, 1H) a-142 13.30 (s, 1H), 8.20 (d, 1H), 7.93 (s, 1H), 7.71 (d, 2H), 7.36 (d, 2H), 7.22 (d, 1H) b-2 11.12 (s, 1H), 7.97 (d, 1H), 7.83 (s, 1H), 7.30 (m, 4H), 7.09 (d, 1H) b-4 11.12 (d, 1H), 8.81 (s, 1H), 8.37 (s, 1H), 8.03 (d, 1H), 7.79 (s, 1H), 7.12 (d, 1H), 5.55 (m, 1H), 1.42 (d, 3H) b-6 11.08 (d, 1H), 8.88 (s, 1H), 8.10 (m, 1H), 8.03 (d, 1H), 7.89 (s, 1H), 7.54 (d, 1H), 7.15 (d, 1H), 5.03 (m, 1H), 1.95-1.87 (m, 2H), 0.91 (m, 3H)

(49) As described above, the sufonylaminobenzamide compound of the present invention can be produced easily by using known chemical reactions such as those described in the example above. The fact that compounds not specifically disclosed in the present description, namely compounds substituted with various substituents which do not depart from the object and scope of the present invention, can be produced and used in accordance with the methods described above or similar methods will be readily understood by those skilled in the art on the basis of the disclosure within the present description.

(50) [Biological Testing]

(51) The test examples described below demonstrate that the sufonylaminobenzanmide compound of the present invention (hereafter also referred to as the compound of the present invention) is useful as the active constituent in a pest control agent. The units parts are based on weight.

(52) (Preparation of Test Emulsion)

(53) Five parts of the compound of the present invention, 93.6 parts of dimethylformamide and 1.4 parts of a polyoxyethylene alkyl aryl ether were mixed together and dissolved to obtain an emulsion (1) containing 5% of the active constituent.

(54) The mortality rate was calculated using the following equation.
Mortality rate (%)=(number of dead pests/number of test pests)100

(Test Example 1) Efficacy Test Against Mythimna separata

(55) First, 0.8 g of an artificial feed (Insecta LFS, manufactured by Nosan Corporation) and 1 l of the emulsion (I) were mixed thoroughly, and 0.2 g of the resulting mixture was placed in each of the treatment areas of a plastic test container (volume: 1.4 ml) to complete preparation of a test feed.

(56) Two second-instar larvae of Mythimna separata were inoculated into each treatment area, and the test container was sealed with a plastic lid. The sealed container was placed in a temperature-controlled room at 25 C., and the mortality rate and the amount of feed consumed were determined on the fifth day. The test was repeated. Further, a test performed under the same conditions, but with the exception of excluding the compound of the present invention from the emulsion (1), was used as a control.

(57) Efficacy tests against Mythimna separata were conducted for the compounds having the compound numbers shown in Table 4. For all of the compounds, the mortality rate against Mythimna separata was 100%, or the amount of feed consumed was 10% or less of the amount of feed consumed in the control.

(58) TABLE-US-00004 TABLE 4 a-1 a-22 a-41 a-65 a-86 a-113 a-133 a-2 a-23 a-42 a-66 a-87 a-114 a-134 a-3 a-24 a-46 a-67 a-88 a-115 a-135 a-4 a-25 a-49 a-68 a-90 a-116 a-137 a-7 a-26 a-50 a-69 a-92 a-117 a-138 a-8 a-28 a-51 a-70 a-96 a-118 a-139 a-9 a-29 a-53 a-71 a-97 a-119 a-141 a-10 a-30 a-54 a-73 a-98 a-120 a-142 a-11 a-31 a-55 a-75 a-99 a-121 a-143 a-12 a-32 a-56 a-76 a-100 a-122 b-1 a-13 a-33 a-57 a-78 a-103 a-123 b-2 a-14 a-34 a-58 a-79 a-104 a-124 b-3 a-15 a-35 a-59 a-80 a-105 a-126 b-4 a-16 a-36 a-60 a-81 a-106 a-127 b-6 a-18 a-37 a-61 a-82 a-109 a-128 a-19 a-38 a-62 a-83 a-110 a-129 a-20 a-39 a-63 a-84 a-111 a-131 a-21 a-40 a-64 a-85 a-112 a-132

(Test Example 2) Efficacy Test Against Spodoptera litura

(59) The emulsion (1) was diluted with water to achieve a concentration of the compound of the present invention of 125 ppm. Cabbage leaves were soaked in the diluted liquid for 30 seconds. These cabbage leaves were then placed in a Petri dish, and five second-instar larvae of Spodoptera litura were released into the dish. The Petri dish was placed in a temperature-controlled room at a temperature of 25 C. and a humidity of 60%. Mortality was investigated 6 days after larvae release, and the mortality rate was calculated. The test was repeated.

(60) Efficacy tests against Spodoptera litura were conducted for the compounds having the compound numbers shown in Table 5. All of the compounds produced a mortality rate against Spodoptera litura of at least 80%.

(61) TABLE-US-00005 TABLE 5 a-1 a-9 a-16 a-23 a-29 a-41 a-64 a-2 a-10 a-18 a-24 a-30 a-42 b-2 a-3 a-11 a-19 a-25 a-34 a-50 b-3 a-4 a-12 a-20 a-26 a-35 a-54 b-4 a-7 a-14 a-21 a-27 a-37 a-55 b-6 a-8 a-15 a-22 a-28 a-39 a-56

(Test Example 3) Efficacy Test Against Plutella xylostella

(62) The emulsion (I) was diluted with water to achieve a concentration of the compound of the present invention of 125 ppm. Cabbage leaves were soaked in the diluted liquid for 30 seconds. These cabbage leaves were then placed in a Petri dish, and five second-instar larvae of Plutella xylostella were released into the dish. The Petri dish was placed in a temperature-controlled room at a temperature of 25 C. and a humidity of 60%. Mortality was investigated 3 days after larvae release, and the mortality rate was calculated. The test was repeated.

(63) Efficacy tests against Plutella xylostella were conducted for the compounds having the compound numbers shown in Table 6. All of the compounds produced a mortality rate against Spodoptera litura of at least 80%.

(64) TABLE-US-00006 TABLE 6 a-1 a-22 a-32 a-40 a-54 a-67 b-6 a-2 a-23 a-33 a-41 a-55 a-76 a-3 a-24 a-34 a-42 a-56 a-78 a-4 a-25 a-35 a-49 a-58 b-1 a-7 a-26 a-36 a-50 a-64 b-2 a-15 a-29 a-37 a-51 a-65 b-3 a-21 a-30 a-39 a-53 a-66 b-4

(Test Example 4) Efficacy Test Against Meloidogyne incognita

(65) (Clubroot Formation Suppression Test)

(66) The emulsion (I) was diluted with water to achieve a concentration of the compound of the present invention of 125 ppm. A plastic container with a diameter of 5 cm was filled with 7 g of a culture medium, and cucumber seeds were planted. The culture medium was irrigated with 1 ml of the above dilute liquid, and then inoculated with 200 eggs of Meloidogyne incognita. The container was then placed in a temperature-controlled room at a temperature of 25 C. and a humidity of 60%, and after 14 days, the clubroot formation suppression ratio (%) relative to an untreated sample was calculated from the number of clubroots formed on the roots of the cucumber plants. The test was repeated.
Clubroot formation suppression ratio (%)=(1Nt/Nc)100

(67) Nt: Total number of club roots formed in two treated samples after 14 days

(68) Nc: Total number of club roots formed in two untreated samples after 14 days

(69) Efficacy tests against Meloidogyne incognita were conducted for the compounds having the compound numbers shown in Table 7. All of the compounds produced a clubroot formation suppression ratio against Meloidogyne incognita of at least 80%.

(70) TABLE-US-00007 TABLE 7 a-1 a-16 a-40 a-59 a-74 a-87 a-102 a-121 a-136 a-2 a-22 a-41 a-60 a-75 a-88 a-103 a-122 a-137 a-3 a-24 a-42 a-61 a-76 a-90 a-109 a-123 a-138 a-4 a-26 a-49 a-62 a-78 a-91 a-110 a-124 a-139 a-6 a-28 a-50 a-63 a-79 a-92 a-111 a-126 a-141 a-7 a-29 a-51 a-64 a-80 a-93 a-112 a-127 a-143 a-8 a-32 a-53 a-67 a-81 a-95 a-113 a-128 b-4 a-9 a-34 a-54 a-68 a-82 a-96 a-115 a-129 b-5 a-10 a-35 a-55 a-69 a-83 a-97 a-116 a-131 b-6 a-11 a-36 a-56 a-70 a-84 a-98 a-118 a-132 a-14 a-38 a-57 a-71 a-85 a-99 a-119 a-134 a-15 a-39 a-58 a-73 a-86 a-100 a-120 a-135

(Test Example 5) Efficacy Test Against Meloidogyne incognita (In Vitro Test)

(71) Two hundred L of a suspension containing about 50 second-instar larvae (L2) of Meloidogyne incognita was dispensed into each well of a 96-well microplate, and 0.2 L of a 10,000 ppm dimethylsulfoxide solution of the compound of the present invention was injected into each well to achieve a final concentration of 50 ppm. Mortality was investigated after 2 days treatment at 15 C., and the nematode mortality rate was calculated. Observation was performed for 10 seconds, and those individuals that showed no movement in that time were deemed to be dead. The test was repeated.

(72) Efficacy tests against Meloidogyne incognita were conducted for the compounds having the compound numbers shown in Table 8. All of the compounds produced a nematode mortality (still) rate against Meloidogyne incognita of at least 80%.

(73) TABLE-US-00008 TABLE 8 a-1 a-17 a-37 a-58 a-76 a-92 a-113 a-131 a-2 a-18 a-38 a-59 a-78 a-93 a-115 a-132 a-3 a-22 a-39 a-60 a-79 a-95 a-116 a-134 a-4 a-24 a-40 a-61 a-80 a-96 a-118 a-135 a-6 a-25 a-41 a-62 a-81 a-97 a-119 a-136 a-7 a-26 a-42 a-63 a-82 a-98 a-120 a-137 a-8 a-28 a-49 a-64 a-83 a-99 a-121 a-138 a-9 a-29 a-50 a-67 a-84 a-100 a-122 a-139 a-10 a-30 a-51 a-68 a-85 a-102 a-123 a-141 a-11 a-32 a-53 a-69 a-86 a-103 a-124 a-143 a-12 a-33 a-54 a-70 a-87 a-109 a-126 b-1 a-14 a-34 a-55 a-71 a-88 a-110 a-127 b-4 a-15 a-35 a-56 a-73 a-90 a-111 a-128 b-5 a-16 a-36 a-57 a-75 a-91 a-112 a-129

(Test Example 6) Efficacy Test Against Caenorhabditis elegans (In Vitro Test)

(74) Two hundred L of a suspension containing about 50 mixed instars of Caenorhabditis elegans was dispensed into each well of a 96-well microplate, and 0.2 L of a 10,000 ppm dimethylsulfoxide solution of the compound of the present invention was injected into each well to achieve a final concentration of 50 ppm. Mortality was investigated after 2 days treatment at 25 C., and the nematode mortality rate was calculated. Observation was performed for 10 seconds, and those individuals that showed no movement in that time were deemed to be dead. The test was repeated.

(75) Efficacy tests against Caenorhabditis elegans were conducted for the compounds having the compound numbers shown in Table 9. All of the compounds produced a nematode mortality rate against Caenorhabditis elegans of at least 80%.

(76) TABLE-US-00009 TABLE 9 a-1 a-16 a-33 a-53 a-68 a-103 a-118 a-137 a-2 a-18 a-34 a-54 a-69 a-104 a-119 a-138 a-3 a-19 a-35 a-55 a-70 a-106 a-120 a-142 a-4 a-20 a-36 a-56 a-75 a-107 a-121 a-143 a-6 a-22 a-37 a-57 a-76 a-109 a-122 b-4 a-7 a-24 a-38 a-58 a-78 a-110 a-123 b-5 a-8 a-25 a-39 a-60 a-79 a-111 a-124 b-6 a-9 a-26 a-40 a-61 a-88 a-112 a-126 a-10 a-28 a-41 a-62 a-90 a-113 a-127 a-11 a-29 a-42 a-63 a-93 a-114 a-128 a-12 a-30 a-49 a-64 a-97 a-115 a-129 a-14 a-31 a-50 a-66 a-98 a-116 a-132 a-15 a-32 a-51 a-67 a-99 a-117 a-133

(Test Example 7) Efficacy Test Against Heterodera glycines (In Vitro Test)

(77) Two hundred L of a suspension containing about 50 second-instar larvae (L2) of Heterodera glycines was dispensed into each well of a 96-well microplate, and 0.2 L of a 10,000 ppm dimethylsulfoxide solution of the compound of the present invention was injected into each well to achieve a final concentration of 10 ppm. Mortality was investigated after 3 days treatment at 25 C., and the nematode mortality rate was calculated. Observation was performed for 10 seconds, and those individuals that showed no movement in that time were deemed to be dead. The test was repeated.

(78) Efficacy tests against Heterodera glycines were conducted for the compounds having the compound numbers shown in Table 10. All of the compounds produced a nematode mortality rate against Heterodera glycines of at least 80%.

(79) TABLE-US-00010 TABLE 10 a-2 a-63 a-135 a-4 a-76 a-136 a-15 a-78 a-58 a-134

(Test Example 8) Contact/Ingestion Efficacy Test Against Aedes aegypti Larvae

(80) A DMSO solution of the compound of the present invention was diluted with water to obtain a 125 M dilute solution. Ten first-instar larvae of Aedes aegypti were placed in each well of a 96-well microtiter plate, the above dilute liquid was added in a ratio of 1/10, and a test was conducted at a final concentration of 12.5 M. The samples were incubated in a temperature-controlled room (28 C., 80% RH), and after 48 hours of treatment with the compound, the mortality of the larvae was investigated. The test was repeated.

(81) Contact/ingestion efficacy tests against Aedes aegypti larvae were conducted for the compounds having the compound numbers shown in Table 11. All of the compounds produced a mortality rate against Aedes aegypti of at least 80%.

(82) TABLE-US-00011 TABLE 11 a-1 a-9 a-18 a-26 a-34 a-42 a-87 a-2 a-10 a-19 a-28 a-35 a-49 a-88 a-3 a-11 a-20 a-29 a-36 a-58 a-93 a-4 a-12 a-22 a-30 a-37 a-60 a-100 a-6 a-14 a-23 a-31 a-39 a-73 b-1 a-7 a-15 a-24 a-32 a-40 a-76 b-2 a-8 a-16 a-25 a-33 a-41 a-78 b-3

(Test Example 9) Efficacy Tests Against Ascaridia galli and Oesophagostomum Dentatum

(83) Using the gut-welling larval stages of two parasitic worms: namely, the third stage larvae (L3) of Ascaridia galli, and the third and fourth stage larvae (L3 and L4 respectively) of Oesophagostomum dentatum, the bioactivity of compounds of the present invention were investigated in vitro. When conducting these tests, DMSO solutions of the compounds of the present invention were prepared at various concentrations and incubated in the wells of a 96-well microtiter plate. Subsequently, 20 parasitic worm larvae were inoculated into each well. The bioactivity was determined by inspection under a microscope. The inspection under a microscope included evaluations of the mortality rate, injury, motility, development progression, and neutral red uptake by the larvae compared with a DMSO control. The bioactivity was defined by the minimum effective concentration (MEC), which represents the concentration at which at least one larva dies, is injured, undergoes a change in motility or a change in development progression, or exhibits no neutral red uptake.

(84) Efficacy tests against Ascaridia galli and Oesophagostomum dentatum were conducted for the compounds having the compound numbers shown in Table 12. All of the compounds exhibited activity against at least one type of target parasitic worm at an MEC of 25 M or less.

(85) TABLE-US-00012 TABLE 12 a-2 a-14 a-25 a-34 a-58 a-93 a-3 a-15 a-26 a-35 a-60 a-100 a-7 a-16 a-28 a-36 a-73 b-1 a-8 a-17 a-29 a-37 a-76 a-9 a-21 a-30 a-41 a-78 a-10 a-23 a-32 a-42 a-87 a-13 a-24 a-33 a-49 a-88

(Test Example 10) Efficacy Test Against Haemonchus contortus

(86) Third stage larvae (L3) of Haemonchus contortus were collected from the feces of infected sheep, and the bioactivity of compounds of the present invention were investigated in vitro. When conducting this test, DMSO solutions of the compounds of the present invention were prepared at various concentrations and incubated in the wells of a 96-well microtiter plate. Subsequently, 100 parasitic worm larvae were inoculated into each well. The bioactivity was determined by inspection under a microscope. The inspection under a microscope included evaluations of the mortality rate, injury, motility, development progression, and neutral red uptake by the larvae compared with a DMSO control. The bioactivity was defined by the minimum effective concentration (MEC), which represents the concentration at which at least one larva dies, is injured, undergoes a change in motility or a change in development progression, or exhibits no neutral red uptake.

(87) Efficacy tests against Haemonchus contortus were conducted for the compounds having the compound numbers shown in Table 13. All of the compounds exhibited activity against L3 larvae of Haemonchus contortus at an MEC of 25 M or less.

(88) TABLE-US-00013 TABLE 13 a-49 a-76 a-93 a-58 a-78 a-100 a-60 a-87 a-73 a-88

(Test Example 11) Efficacy Test Against Dirofilaria immitis

(89) Using the microfilarial stage and the fourth stage larvae (Mf and L4 respectively) of Dirofilaria immitis, the bioactivity of compounds of the present invention were investigated in vitro. The Mf was collected from the blood of infected dogs, and 500 microfilariae were inoculated into each well of a 96-well microtiter plate. The L4 larvae was obtained by allowing L3 larvae collected from infected mosquitoes to undergo a single molt, and 10 of these L4 larvae were inoculated into each well. Subsequently, a 10 mM DMSO solution of the compound of the present invention was prepared at various concentrations and added to each well in a ratio of 1/1,000, and a test was then conducted at a final concentration of 10 M. Incubation was performed at 37 C. in an environment containing 5% carbon dioxide, and 72 hours after treatment with the compound, the mortality and growth inhibition were determined. The test was repeated.

(90) An efficacy test against Dirofilaria immitis was conducted for the compound having the compound number a-26. At 10 M, this compound exhibited a mortality rate or growth inhibition rate of at least 90% against both the Mf and L4 growth stages.

(91) Based on the fact that compounds selected randomly from the compounds of the present invention all exhibited the types of effects described above, it is evident that the compounds of the present invention, including those compounds not exemplified above, have pest control effects, and in particular, insecticidal, miticidal and nematicidal effects or the like.

INDUSTRIAL APPLICABILITY

(92) The present invention can provide a sufonylaminobenzamide compound that has pest control activity, and in particular, has excellent insecticidal, miticidal and/or nematicidal activity, exhibits excellent safety, and can be synthesized favorably on an industrial scale, and can also provide a pest control agent that contains this compound as an active constituent.