INSECTICIDAL COMPOUNDS

Abstract

The present invention relates to compounds of formula (I) wherein A.sup.1, A.sup.2, A.sup.3, A.sup.4, R.sup.1, R.sup.2, R.sup.3, R.sup.4 and n are as defined in claim 1; or a tautomer, isomer, enantiomer, salt or N-oxide thereof; to intermediates for preparing compounds of formula (I), to compositions comprising them and to methods of using them to combat and control insect, acarine, nematode and mollusc pests.

##STR00001##

Claims

1. A compound of formula (I) ##STR00015## wherein A.sup.1, A.sup.2, A.sup.3 and A.sup.4 are independently of one another C—H, C—R.sup.5, or nitrogen; R.sup.1 is selected from —(C.sub.0-C.sub.4alkyl)-C(═O)—C.sub.3-C.sub.6cycloalkyl, —(C.sub.0-C.sub.4alkyl)-O—C(═O)—C.sub.3-C.sub.6cycloalkyl, —(C.sub.0-C.sub.4alkyl)-O—C.sub.3-C.sub.6cycloalkyl, —R.sup.1aOR.sup.1aOR.sup.1b, —R.sup.1aOC(═O)R.sup.1b, —R.sup.1aOC(═O)OR.sup.1b, —R.sup.1aN(R.sup.1c)C(═O)OR.sup.1b, —R.sup.1aOC(═O)N(R.sup.1b)(R.sup.1c), —R.sup.1aC(═O)N(R.sup.1b)(R.sup.1c) and —S—C(═O)OR.sup.1b; R.sup.1a is —(CR.sup.1dR.sup.1e).sub.m—; R.sup.1b and R.sup.1c are independently selected from hydrogen and C.sub.1-C.sub.4alkyl, wherein each alkyl group is unsubstituted or substituted with one to three halogen atoms or with a cyano group; R.sup.1d and R.sup.1e are independently selected from hydrogen and C.sub.1-C.sub.4alkyl; m is selected from 1, 2, 3 and 4; R.sup.2 is C.sub.1-C.sub.8alkyl, C.sub.1-C.sub.8alkyl substituted by one to three R.sup.6a, C.sub.1-C.sub.8haloalkyl, C.sub.1-C.sub.8haloalkyl substituted by one to three R.sup.6a, C.sub.3-C.sub.8cycloalkyl, C.sub.3-C.sub.8cycloalkyl substituted by one to three R.sup.6b, C.sub.3-C.sub.8cycloalkyl where one carbon atom is replaced by O, S, S(O) or SO.sub.2, C.sub.3-C.sub.8cycloalkyl-C.sub.1-C.sub.8alkyl, C.sub.3-C.sub.8cycloalkyl-C.sub.1-C.sub.8alkyl where one carbon atom in the cycloalkyl group is replaced by O, S, S(O) or SO.sub.2, C.sub.3-C.sub.8cycloalkyl-C.sub.1-C.sub.8haloalkyl, C.sub.2-C.sub.8alkenyl, C.sub.2-C.sub.8alkenyl substituted by one to three R.sup.6a, C.sub.2-C.sub.8haloalkenyl, C.sub.2-C.sub.8haloalkenyl substituted by one to three R.sup.6a, C.sub.2-C.sub.8alkynyl, C.sub.2-C.sub.8haloalkynyl, phenyl, phenyl substituted by one to three R.sup.7, phenyl-C.sub.1-C.sub.4alkyl, phenyl-C.sub.1-C.sub.4alkyl wherein the phenyl moiety is substituted by one to three R.sup.7, 5-6 membered heteroaryl, 5-6 membered heteroaryl substituted by one to three R.sup.7, 5-6 membered heteroaryl-C.sub.1-C.sub.4alkyl, 5-6 membered heteroaryl-C.sub.1-C.sub.4alkyl wherein the heteroaryl moiety is substituted by one to three R.sup.7, —N(R.sup.8)(R.sup.9), halogen or —OR.sup.10; R.sup.3 is C.sub.1-C.sub.8haloalkyl; R.sup.4 is aryl, aryl substituted by one to three R.sup.7, heteroaryl or heteroaryl substituted by one to three R.sup.7; R.sup.5 is independently halogen, cyano, nitro, C.sub.1-C.sub.8alkyl, C.sub.3-C.sub.8cycloalkyl, C.sub.1-C.sub.8haloalkyl, C.sub.2-C.sub.8alkenyl, C.sub.2-C.sub.8haloalkenyl, C.sub.2-C.sub.8alkynyl, C.sub.2-C.sub.8haloalkynyl, C.sub.1-C.sub.8alkoxy, C.sub.1-C.sub.8haloalkoxy, or C.sub.1-C.sub.8alkoxycarbonyl-, or two R.sup.5 on adjacent carbon atoms together form a —CH═CH—CH═CH— bridge or a —N═CH—CH═CH— bridge; R.sup.6a is independently cyano, nitro, amino, C.sub.1-C.sub.8alkylamino, N,N—C.sub.1-C.sub.8dialkylamino, hydroxy, C.sub.1-C.sub.8alkoxy, or C.sub.1-C.sub.8haloalkoxy; R.sup.6b is independently halogen, cyano, nitro, oxo, C.sub.1-C.sub.8alkyl, C.sub.1-C.sub.8haloalkyl, amino, C.sub.1-C.sub.8alkylamino, N,N—C.sub.1-C.sub.8dialkylamino, hydroxyl, C.sub.1-C.sub.8alkoxy, C.sub.1-C.sub.8haloalkoxy, phenyl, phenyl substituted by one to three R.sup.7, 5-6 membered heteroaryl, 5-6 membered heteroaryl substituted by one to three R.sup.7; R.sup.7 is independently halogen, cyano, nitro, C.sub.1-C.sub.8alkyl, C.sub.1-C.sub.8haloalkyl, C.sub.1-C.sub.8alkoxy, C.sub.1-C.sub.8haloalkoxy; R.sup.8 and R.sup.9 are independently hydrogen, cyano, cyano-C.sub.1-C.sub.8alkyl, C.sub.1-C.sub.8alkyl, C.sub.1-C.sub.8alkyl substituted by one to three R.sup.6a, C.sub.2-C.sub.8alkenyl, C.sub.2-C.sub.8alkenyl substituted by one to three R.sup.6a, C.sub.1-C.sub.8alkoxy, C.sub.1-C.sub.8haloalkoxy, C.sub.1-C.sub.8haloalkoxy substituted by one to three R.sup.6a, C.sub.1-C.sub.8alkoxy substituted by one to three R.sup.6a, C.sub.1-C.sub.8haloalkyl, C.sub.1-C.sub.8haloalkyl substituted by one to three R.sup.6a, C.sub.3-C.sub.8cycloalkyl, C.sub.3-C.sub.8cycloalkyl substituted by one to three R.sup.6b, C.sub.3-C.sub.8cycloalkyl where one carbon atom is replaced by O, S, S(O) or SO.sub.2, C.sub.3-C.sub.8cycloalkyl-C.sub.1-C.sub.8alkyl, C.sub.3-C.sub.8cycloalkyl-C.sub.1-C.sub.8alkyl where one carbon atom in the cycloalkyl group is replaced by O, S, S(O) or SO.sub.2, C.sub.3-C.sub.8cycloalkyl-C.sub.1-C.sub.8haloalkyl, C.sub.2-C.sub.8alkenyl, C.sub.2-C.sub.8alkenyl substituted by one to three R.sup.6a, C.sub.2-C.sub.8haloalkenyl, C.sub.2-C.sub.8haloalkenyl substituted by one to three R.sup.6a, C.sub.2-C.sub.8alkynyl, C.sub.2-C.sub.8haloalkynyl, phenyl, phenyl substituted by one to three R.sup.7, phenyl-C.sub.1-C.sub.4alkyl, phenyl-C.sub.1-C.sub.4alkyl wherein the phenyl moiety is substituted by one to three R.sup.7, 5-6 membered heteroaryl, 5-6 membered heteroaryl substituted by one to three R.sup.7, 5-6 membered heteroaryl-C.sub.1-C.sub.4alkyl, 5-6 membered heteroaryl-C.sub.1-C.sub.4alkyl wherein the heteroaryl moiety is substituted by one to three R.sup.7, —S(O)R.sup.10, —S(O).sub.2R.sup.10, COR.sup.10, COOR.sup.10, or R.sup.8 and R.sup.9 together with the nitrogen atom may be linked through a C.sub.3-C.sub.8alkylene chain, a C.sub.3-C.sub.8alkylene chain substituted by one to three R.sup.6b or a C.sub.3-C.sub.8alkylene chain, where one carbon atom is replaced by O, S, S(O) or SO.sub.2; R.sup.10 is hydrogen, cyano-C.sub.1-C.sub.8alkyl, C.sub.1-C.sub.8alkyl, C.sub.1-C.sub.8alkyl substituted by one to three R.sup.6a, C.sub.1-C.sub.8haloalkyl, C.sub.1-C.sub.8haloalkyl substituted by one to three R.sup.6a, C.sub.3-C.sub.8cycloalkyl, C.sub.3-C.sub.8cycloalkyl substituted by one to three R.sup.6b, C.sub.3-C.sub.8cycloalkyl where one carbon atom is replaced by O, S, S(O) or SO.sub.2, C.sub.3-C.sub.8cycloalkyl-C.sub.1-C.sub.8alkyl, C.sub.3-C.sub.8cycloalkyl-C.sub.1-C.sub.8alkyl where one carbon atom in the cycloalkyl group is replaced by O, S, S(O) or SO.sub.2, C.sub.3-C.sub.8cycloalkyl-C.sub.1-C.sub.8haloalkyl, C.sub.2-C.sub.8alkenyl, C.sub.2-C.sub.8alkenyl substituted by one to three R.sup.6a, C.sub.2-C.sub.8haloalkenyl, C.sub.2-C.sub.8haloalkenyl substituted by one to three R.sup.6a, C.sub.2-C.sub.8alkynyl, C.sub.2-C.sub.8haloalkynyl, phenyl, phenyl substituted by one to three R.sup.7, phenyl-C.sub.1-C.sub.4alkyl, phenyl-C.sub.1-C.sub.4alkyl wherein the phenyl moiety is substituted by one to three R.sup.7, 5-6 membered heteroaryl, 5-6 membered heteroaryl substituted by one to three R.sup.7, 5-6 membered heteroaryl-C.sub.1-C.sub.4alkyl or 5-6 membered heteroaryl-C.sub.1-C.sub.4alkyl wherein the heteroaryl moiety is substituted by one to three R.sup.7; n is 1 or 2; or a tautomer, isomer, enantiomer, salt or N-oxide thereof.

2. The compound according to claim 1, wherein A.sup.1 is C—R.sup.5; A.sup.2 is C—H; A.sup.3 is C—H; and A.sup.4 is C—H, wherein R.sup.5 is halogen, cyano, nitro, C.sub.1-C.sub.8alkyl, C.sub.3-C.sub.8cycloalkyl, C.sub.1-C.sub.8haloalkyl, or C.sub.2-C.sub.8alkenyl.

3. The compound according to claim 1, wherein R.sup.1 is selected from —(C.sub.0-C.sub.4alkyl)-C(═O)—C.sub.3-C.sub.6cycloalkyl and —(C.sub.0-C.sub.4alkyl)-O—C.sub.3-C.sub.6cycloalkyl.

4. The compound according to claim 1, wherein R.sup.2 is C.sub.1-C.sub.8haloalkyl.

5. The compound according to claim 1, wherein R.sup.3 is C.sub.1-C.sub.4haloalkyl.

6. The compound according to claim 1, wherein R.sup.4 is phenyl or phenyl substituted by one to three R.sup.7; wherein R.sup.7 is independently halogen, cyano, C.sub.1-C.sub.8alkyl, C.sub.1-C.sub.8haloalkyl, C.sub.1-C.sub.8alkoxy, or C.sub.1-C.sub.8haloalkoxy.

7. The compound according to claim 1, wherein A.sup.1 is CR.sup.5 and A.sup.2, A.sup.3 and A.sup.4 are each CH; R.sup.1 is selected from —(C.sub.0-C.sub.4alkyl)-C(═O)—C.sub.3-C.sub.6cycloalkyl and —(C.sub.0-C.sub.4alkyl)-O—C.sub.3-C.sub.6cycloalkyl; R.sup.2 is C.sub.1-C.sub.8haloalkyl; R.sup.3 is C.sub.1-C.sub.4haloalkyl; R.sup.4 is aryl or aryl substituted by one to three R.sup.6b; and n is 2; wherein R.sup.5 is C.sub.1-C.sub.8alkyl; and R.sup.6b is independently halogen, cyano, nitro, C.sub.1-C.sub.4alkyl, or C.sub.1-C.sub.4haloalkyl, C.sub.1-C.sub.4alkoxy, or C.sub.1-C.sub.4haloalkoxy.

8. The compound according to claim 1 represented by the compounds of formula (Ia) ##STR00016## wherein R.sup.1 is selected from —(C.sub.0-C.sub.4alkyl)-C(═O)—C.sub.3-C.sub.6cycloalkyl, —(C.sub.0-C.sub.4alkyl)-O—C(═O)—C.sub.3-C.sub.6cycloalkyl, —(C.sub.0-C.sub.4alkyl)-O—C.sub.3-C.sub.6cycloalkyl, —R.sup.1aOR.sup.1aOR.sup.1b, —R.sup.1aOC(═O)R.sup.1b, —R.sup.1aOC(═O)OR.sup.1b, —R.sup.1aN(R.sup.1c)C(═O)OR.sup.1b, —R.sup.1aOC(═O)N(R.sup.1b)(R.sup.1c), —R.sup.1aC(═O)N(R.sup.1b)(R.sup.1c) and —S—C(═O)OR.sup.1b; R.sup.1a is —(CR.sup.1dR.sup.1e).sub.m—; R.sup.1b and R.sup.1c are independently selected from H and C.sub.1-C.sub.4alkyl, wherein each alkyl group is unsubstituted or substituted with one to three halogen atoms or with a cyano group; R.sup.1d and R.sup.1e are independently selected from H and C.sub.1-C.sub.4alkyl; m is selected from 1, 2, 3 and 4.

9. A compound of formula (Int-I) ##STR00017## wherein A.sup.1, A.sup.2, A.sup.3, A.sup.4, R.sup.1 and R.sup.2, are as defined according to claim 1 and X.sup.B is a leaving group, or X.sup.B is cyano, formyl, CH═N—OH or acetyl; or a tautomer, isomer, enantiomer, salt or N-oxide thereof; or a compound of formula (Int-II) ##STR00018## wherein A.sup.1, A.sup.2, A.sup.3, A.sup.4, R.sup.1 and R.sup.2, are as defined according to claim 1, and X.sup.C is CH.sub.2-halogen, CH═C(R.sup.3)R.sup.4, or CH.sub.2C(OH)(R.sup.3)R.sup.4, wherein R.sup.3 and R.sup.4 are as defined for a compound of formula (I), according to claim 1; or a tautomer, isomer, enantiomer, salt or N-oxide thereof; or a compound of formula (Int-III) ##STR00019## wherein R.sup.1 and R.sup.2 are as defined for a compound of formula (I), according to claim 1; or a tautomer, isomer, enantiomer, salt or N-oxide thereof.

10. A method of combating and/or controlling an invertebrate animal pest which comprises applying to the pest, to a locus of the pest, or to a plant susceptible to attack by the pest a pesticidally effective amount of a compound of formula (I), as defined in claim 1.

11. A pesticidal composition, which comprises at least one compound of formula (I) according to claim 1, or where appropriate a tautomer thereof, in each case in free form or in agrochemically utilizable salt form, as active ingredient.

12. A method for controlling pests, which comprises applying a composition according to claim 11 to the pests or their environment with the exception of a method for treatment of the human or animal body by surgery or therapy and diagnostic methods practised on the human or animal body.

13. A method for the protection of plant propagation material from the attack by pests, which comprises treating the propagation material or the site, where the propagation material is planted, with a composition according to claim 11.

14. A plant propagation material treated with the pesticidal composition described in claim 11.

Description

PREPARATORY EXAMPLES

[0186] “Mp” means melting point in ° C. Free radicals represent methyl groups. .sup.1H NMR measurements were recorded on a Brucker 400 MHz spectrometer, chemical shifts are given in ppm relevant to a TMS standard. Spectra measured in deuterated solvents as indicated.

Example 1: preparation of N-(cyclopropoxymethyl)-4-[(5S)-5-(3,5-dichloro-4-fluoro-phenyl)-5-(trifluoromethyl)-4H-isoxazol-3-yl]-N-[(4R)-2-(difluoromethylsulfonyl)isoxazolidin-4-yl]-2-methyl-benzamide (Compound A2)

[0187] To a mixture of 4-[(5S)-5-(3,5-dichloro-4-fluoro-phenyl)-5-(trifluoromethyl)-4H-isoxazol-3-yl]-N-[(4R)-2-(difluoromethylsulfonyl)isoxazolidin-4-yl]-2-methyl-benzamide (1.5 g) and paraformaldehyde (300 mg) in dichloromethane (12 mL) was added triethylamine (1.02 mL) at 0° C., under argon atmosphere, and the mixture was stirred for 15 minutes. To the mixture was then added dropwise titanium (IV) chloride (7.25 mL, 1 mol/L in toluene) at 0° C. and the reaction mixture was allowed to warm to ambient temperature and stirred for 5 hours 30 minutes. After, this reaction mixture was divided and into 4 equal volumes of reaction media and transfered to new reaction vials. Then, to each of the 4 individual reaction vials was introduced cyclopropanol (0.394 mL) at ambient temperature and the contents were stirred for 45 minutes. Afterwards, an additional amount of cyclopropanol (0.4 mL) was added and the reaction mixture was stirred at ambient temperature for an additional 2 hours. The reaction mixture was then diluted with water and ethyl acetate. The aqueous layer was separated and extracted twice with ethyl acetate. The total combined organic layer was dried over sodium sulfate, filtered, and concentrated under vacuum to afford a crude residue which was purified by Combiflash chromatography (eluent:gradient cyclohexane/ethyl acetate 1:0 to 60:40), to give 141 mg of the desired product A2. .sup.1H NMR (400 MHz, CDCl.sub.3) δ ppm 7.50-7.65 (m, 4H) 7.32 (d, 1H) 6.48 (t, 1H) 5.48-5.56 (m, 1H) 4.53 (br s, 2H) 4.29-4.50 (m, 3H) 4.10 (d, 1H) 3.84 (br dd, 1H) 3.71 (d, 1H) 2.97 (m, 1H) 2.32 (s, 3H) 0.24-0.41 (m, 4H). .sup.19F NMR (377 MHz, CDCl.sub.3) δ ppm −79.55 (s, 3F) −113.45 (s, 1F) −121.02 (d, 1F) −123.62 (d, 1F)

Example 2: Preparation of N-(cyclopropanecarbonyl)-4-[(5S)-5-(3,5-dichloro-4-fluoro-phenyl)-5-(trifluoromethyl)-4H-isoxazol-3-yl]-N-[(4R)-2-(difluoromethylsulfonyl)isoxazolidin-4-yl]-2-methyl-benzamide (Compound A1)

[0188] To a mixture of 4-[(5S)-5-(3,5-dichloro-4-fluoro-phenyl)-5-(trifluoromethyl)-4H-isoxazol-3-yl]-N-[(4R)-2-(difluoromethylsulfonyl)isoxazolidin-4-yl]-2-methyl-benzamide (150 mg) and N,N-dimethylaminopyridine (6 mg) in dry dichloromethane (3.2 mL) was added triethylamine (0.12 mL) followed by cyclopropanecarbonyl chloride (77 mg) and the reaction mixture was stirred at ambient temperature for 3 days. Afterwards, the reaction mixture was diluted with water and ethyl acetate. The aqueous layer was separated, extracted twice with ethyl acetate, and the total combined organic layer was dried over sodium sulfate, filtered, and concentrated under vacuum to afford a crude residue which was purified by Combiflash chromatography (eluent: gradient cyclohexane/ethyl acetate 100:0 to 75:25) and reverse phase preparative HPLC to give 72 mg of the desired product A1. .sup.1H NMR (400 MHz, CDCl.sub.3) δ ppm 7.53-7.62 (m, 4H) 7.37 (d, 1H) 6.27-6.65 (m, 1H) 5.52-5.59 (m, 1H) 4.48 (t, 1H) 4.25-4.34 (m, 2H) 4.10 (d, 1H) 3.96 (br dd, 1H) 3.70 (d, 1H) 2.50 (s, 3H) 1.22-1.30 (m, 1H) 1.03 (br d, 2H) 0.62 (br d, 2H). .sup.19F NMR (377 MHz, CDCl.sub.3) δ ppm −79.55 (s, 3F) −113.24 (s, 1F) −120.83 (d, 1F) −124.31 (d, 1F).

TABLE-US-00004 Compound number IUPAC name Chemical structure A1 N-(cyclopropanecarbonyl)-4-[(5S)-5-(3,5- dichloro-4-fluoro-phenyl)-5- (trifluoromethyl)-4H-isoxazol-3-yl]-N-[(4R)- 2-(difluoromethylsulfonyl)isoxazolidin-4-yl]- 2-methyl-benzamide [00013] A2 N-(cyclopropoxymethyl)-4-[(5S)-5-(3,5- dichloro-4-fluoro-phenyl)-5- (trifluoromethyl)-4H-isoxazol-3-yl]-N-[(4R)- 2-(difluoromethylsulfonyl)isoxazolidin-4-yl]- 2-methyl-benzamide [00014]

BIOLOGICAL EXAMPLES

[0189] These Examples illustrate the pesticidal/insecticidal properties of compounds of formula (I).

[0190] Tests were performed as follows:

Example B1: Diabrotica balteata (Corn Root Worm)

[0191] Maize sprouts placed onto an agar layer in 24-well microtiter plates were treated with aqueous test solutions prepared from 10′000 ppm DMSO stock solutions by spraying. After drying, the plates were infested with L2 larvae (6 to 10 per well). The samples were assessed for mortality and growth inhibition in comparison to untreated samples 4 days after infestation.

[0192] The following compounds gave an effect of at least 80% in at least one of the two categories (mortality or growth inhibition) at an application rate of 200 ppm: A1

Example B2: Euschistus heros (Neotropical Brown Stink Bug)

[0193] Soybean leaves on agar in 24-well microtiter plates were sprayed with aqueous test solutions prepared from 10′000 ppm DMSO stock solutions. After drying the leaves were infested with N2 nymphs. The samples were assessed for mortality and growth inhibition in comparison to untreated samples 5 days after infestation.

[0194] The following compounds gave an effect of at least 80% in at least one of the two categories (mortality or growth inhibition) at an application rate of 200 ppm: A1, A2.

Example B3: Plutella xylostella (Diamond Back Moth)

[0195] 24-well microtiter plates with artificial diet were treated with aqueous test solutions prepared from 10′000 ppm DMSO stock solutions by pipetting. After drying, Plutella eggs were pipetted through a plastic stencil onto a gel blotting paper and the plate was closed with it. The samples were assessed for mortality and growth inhibition in comparison to untreated samples 8 days after infestation.

[0196] The following compounds gave an effect of at least 80% in at least one of the two categories (mortality or growth inhibition) at an application rate of 200 ppm: A2

Example B4: Plutella xylostella (Diamond Back Moth)

[0197] 24-well microtiter plates with artificial diet were treated with aqueous test solutions prepared from 10′000 ppm DMSO stock solutions by pipetting. After drying, the plates were infested with L2 larvae (10 to 15 per well). The samples were assessed for mortality and growth inhibition in comparison to untreated samples 5 days after infestation.

[0198] The following compounds gave an effect of at least 80% in at least one of the two categories (mortality or growth inhibition) at an application rate of 200 ppm: A1

Example B5: Myzus persicae (Green Peach Aphid): Feeding/Contact Activity

[0199] Sunflower leaf discs were placed onto agar in a 24-well microtiter plate and sprayed with aqueous test solutions prepared from 10′000 ppm DMSO stock solutions. After drying, the leaf discs were infested with an aphid population of mixed ages. The samples were assessed for mortality 6 days after infestation.

[0200] The following compounds resulted in at least 80% mortality at an application rate of 200 ppm: A1

Example B6: Spodoptera littoralis (Egyptian Cotton Leaf Worm)

[0201] Cotton leaf discs were placed onto agar in 24-well microtiter plates and sprayed with aqueous test solutions prepared from 10′000 ppm DMSO stock solutions. After drying the leaf discs were infested with five L1 larvae. The samples were assessed for mortality, anti-feeding effect, and growth inhibition in comparison to untreated samples 3 days after infestation. Control of Spodoptera littoralis by a test sample is given when at least one of the categories mortality, anti-feedant effect, and growth inhibition is higher than the untreated sample.

[0202] The following compounds resulted in at least 80% control at an application rate of 200 ppm: A1, A2

Example B7: Tetranychus urticae (Two-Spotted Spider Mite): Feeding/Contact Activity

[0203] Bean leaf discs on agar in 24-well microtiter plates were sprayed with aqueous test solutions prepared from 10′000 ppm DMSO stock solutions. After drying the leaf discs were infested with a mite population of mixed ages. The samples were assessed for mortality on mixed population (mobile stages) 8 days after infestation.

[0204] The following compounds resulted in at least 80% mortality at an application rate of 200 ppm: A1

Example B8: Thrips tabaci (Onion Thrips) Feeding/Contact Activity

[0205] Sunflower leaf discs were placed on agar in 24-well microtiter plates and sprayed with aqueous test solutions prepared from 10′000 ppm DMSO stock solutions. After drying the leaf discs were infested with a thrips population of mixed ages. The samples were assessed for mortality 6 days after infestation. The following compounds resulted in at least 80% mortality at an application rate of 200 ppm: A1