Pesticidally active oxime and hydrazone derivatives
10336691 ยท 2019-07-02
Assignee
Inventors
Cpc classification
C07C271/60
CHEMISTRY; METALLURGY
A01N47/24
HUMAN NECESSITIES
C07C337/08
CHEMISTRY; METALLURGY
A01N47/34
HUMAN NECESSITIES
C07C2602/08
CHEMISTRY; METALLURGY
International classification
C07C271/60
CHEMISTRY; METALLURGY
C07C281/14
CHEMISTRY; METALLURGY
C07C337/08
CHEMISTRY; METALLURGY
A01N47/24
HUMAN NECESSITIES
Abstract
The present invention relates to compounds of formula (I) as defined herein, to processes for preparing them, to pesticidal, in particular insecticidal, acaricidal, molluscicidal and nematicidal compositions comprising them and to methods of using them to combat and control pests such as insect, acarine, mollusc and nematode pests. ##STR00001##
Claims
1. A compound of formula (I) ##STR00112## wherein Ar.sup.1 is phenyl which is unsubstituted or substituted by one to three substituents independently selected from C.sub.1-C.sub.6alkyl, C.sub.3-C.sub.6cycloalkyl, C.sub.1-C.sub.6haloalkyl, C.sub.3-C.sub.6halocycloalkyl, C.sub.1-C.sub.3haloalkyl-C.sub.3-C.sub.6cycloalkyl, C.sub.3-C.sub.6cycloalkoxy, halogen, C.sub.1-C.sub.6alkoxy and C.sub.1-C.sub.6haloalkoxy; Ar.sup.2 is phenyl which is unsubstituted or substituted by one to three substituents independently selected from C.sub.1-C.sub.6alkyl, C.sub.2-C.sub.6alkenyl, C.sub.2-C.sub.6alkynyl, C.sub.3-C.sub.6cycloalkyl, C.sub.1-C.sub.6haloalkyl, C.sub.3-C.sub.6halocycloalkyl, C.sub.1-C.sub.3haloalkyl-C.sub.3-C.sub.6cycloalkyl, C.sub.3-C.sub.6cycloalkoxy, halogen, cyano, C.sub.1-C.sub.6alkoxy, C.sub.1-C.sub.6haloalkoxy and SC.sub.1-C.sub.6alkyl; X.sup.1 is O or NR.sup.6; X.sup.2 is a bond, CH.sub.2 or CH.sub.2CH.sub.2; W is O or NR.sup.2; Y is oxygen or sulfur; R.sup.1 is hydrogen or C.sub.1-C.sub.6alkyl; R.sup.2 is selected from hydrogen, C.sub.1-C.sub.6alkyl and C.sub.1-C.sub.6haloalkyl; R.sup.3 is selected from hydrogen, C.sub.1-C.sub.6alkyl and C.sub.1-C.sub.6haloalkyl; R.sup.6 is hydrogen or C.sub.1-C.sub.6alkyl; J is a group selected from J.sup.1, J.sup.2, J.sup.3, J.sup.9 and J.sup.11: ##STR00113## wherein n is 0, 1 or 2, and R.sup.20 is independently selected from hydrogen, C.sub.3-C.sub.6halocycloalkyl and C.sub.1-C.sub.6haloalkoxy; R.sup.Y is C.sub.1-C.sub.6alkyl; or J and R.sup.Y together with the carbon atom to which they are attached form a bicyclic ring of formula ##STR00114## q is 1 or 2; R.sup.16 and R.sup.17 are independently selected from hydrogen, C.sub.3-C.sub.6halocycloalkyl and C.sub.1-C.sub.6haloalkoxy; or an agrochemically acceptable salt, stereoisomer, tautomer, N-oxide thereof.
2. A compound according to claim 1, of formula (Ia) ##STR00115## or formula (Ib) ##STR00116## wherein R.sup.a, R.sup.b and R.sup.c are independently selected from hydrogen, C.sub.1-C.sub.6alkyl, C.sub.1-C.sub.6haloalkyl, halogen, C.sub.1-C.sub.6alkoxy and C.sub.1-C.sub.6haloalkoxy; X.sup.1 is O or NR.sup.6; X.sup.2 is a bond, CH.sub.2or CH.sub.2CH.sub.2; W is O or NR.sup.2; Y is oxygen or sulfur; R.sup.1 is hydrogen or methyl; R.sup.2 is hydrogen or C.sub.1-C.sub.6alkyl; R.sup.6 is hydrogen or C.sub.1-C.sub.6alkyl; R.sup.16 is C.sub.1-C.sub.6haloalkoxy; or an agrochemically acceptable salt, stereoisomer, tautomer, N-oxide thereof.
3. A compound according to claim l, of formula (Ia) ##STR00117## wherein R.sup.a is R.sup.b and R.sup.c are independently selected from hydrogen, methyl, isopropyl, trifluoromethyl, chloro, fluoro, methoxy and OCF.sub.3; X.sup.1 is selected from O, NH and NCH.sub.3; X.sup.2 is a bond; W is selected from O, NH and NCH.sub.3; Y is oxygen or sulfur; R.sup.1 is hydrogen or methyl; R.sup.16 is OCF.sub.3 or OCF.sub.2CF.sub.3; or an agrochemically acceptable salt, stereoisomer, tautomer, N-oxide thereof.
4. A compound according to claim 1, of formula (Ib) ##STR00118## wherein R.sup.a, R.sup.b and R.sup.c are independently selected from hydrogen, C.sub.1-C.sub.6alkyl, C.sub.1-C.sub.6haloalkyl, halogen, C.sub.1-C.sub.6alkoxy and C.sub.1-C.sub.6haloalkoxy; X.sup.1 is O or NR.sup.6; X.sup.2 is a bond, CH.sub.2 or CH.sub.2CH.sub.2; W is O or NR.sup.2; Y is oxygen or sulfur; R.sup.1 is hydrogen or methyl; R.sup.2 is hydrogen or C.sub.1-C.sub.6alkyl; R.sup.6 is hydrogen or C.sub.1-C.sub.6alkyl; R.sup.16 is C .sub.1 -C.sub.6haloalkoxy; or an agrochemically acceptable salt, stereoisomer, tautomer, N-oxide thereof.
5. A compound according to claim 1, of formula (Ib) ##STR00119## wherein R.sup.a is R.sup.b and R.sup.c are independently selected from hydrogen, methyl, isopropyl, trifluoromethyl, chloro, fluoro, methoxy and OCF.sub.3; X.sup.1 is selected from O, NH and NCH.sub.3; X.sup.2 is a bond; W is selected from O, NH and NCH.sub.3; Y is oxygen or sulfur; R.sup.1 is hydrogen or methyl; R.sup.16 is OCF.sub.3 or OCF.sub.2CF.sub.3; or an agrochemically acceptable salt, stereoisomer, tautomer, N-oxide thereof.
6. A compound selected from TABLE-US-00004 Example No. Structures IUPAC Name 1
7. A pesticidal composition, which comprises at least one compound according to claim 1, or an agrochemically acceptable salt, stereoisomer, tautomer, N-oxide thereof, as active ingredient and at least one auxiliary.
8. The composition according to claim 7, which further comprises one or more other insecticidally, acaricidally, nematicidally and/or fungicidally active agents.
9. A method for controlling pests, which comprises applying a composition according to claim 7 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 practiced on the human or animal body.
10. 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 7.
11. A coated plant propagation material, wherein the coating of the plant propagation material comprises a compound as defined in claim 1.
Description
EXPERIMENTAL
(1) Preparatory Examples: The following examples are intended to illustrate the invention and are not to be construed as being limitations thereon.
(2) Mp means melting point in C. .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 [1-(2,6-dimethylphenyl)-3-[[4-[[5-(trifluoromethoxy)indan-1-ylidene]amino]oxyphenyl]methyleneamino]urea
(3) ##STR00066##
(4) Step A-1: Preparation of 4-[[5-(trifluoromethoxy)indan-1-ylidene]amino]oxybenzonitrile
(5) ##STR00067##
(6) To a solution of 5-(trifluoromethoxy)indan-1-one oxime (1.0 eq., 2.07 g) in N,N-dimethylformamide (295 mL), 4-fluorobenzonitrile (1.0 eq., 1.08 g) and potassium tert-butoxyde (1.2 eq., 10.7 mL of 1M solution in tetrahydrofuran) were added dropwise under argon at 0 C. The mixture was then allowed to warm to room temperature. After 1 h, the reaction mixture was slowly poured into a mixture of HCl (1M)/ethyl acetate. The organic layer was washed with water, brine, dried over Na.sub.2SO.sub.4, filtrated and evaporated. The residue was submitted to column chromatography to give the title compound as a solid.
(7) .sup.1H NMR (400 MHz, CDCl.sub.3) ppm: 7.86 (d, 1H), 7.56-7.71 (m, 2H), 7.31-7.44 (m, 2H), 7.12-7.26 (m, 2H), 3.18 (s, 4H)
(8) Step A-2: Preparation of 4-[[5-(trifluoromethoxy)indan-1-ylidene]amino]oxybenzaldehyde
(9) ##STR00068##
(10) To a solution of 4-[([6-(trifluoromethoxy)indan-1-ylidene]amino]oxybenzonitrile (1.0 eq., 1.968 g) in dichloromethane (59 mL) was added DIBAL-H (1.0 mol/L) in dichloromethane (1.1 eq., 6.5 mL, 8.0 g) at 0 C. The mixture was stirred at this temperature for 1 h, then quenched by careful addition of water at 0 C. and allowed to warm to room temperature. The aqueous layer was extracted twice with ethyl acetate, the organic phase dried over sodium sulphate and the solvent evaporated. The crude reaction mixture was used without purification in the following step.
(11) Step A-3: Preparation of [1-(2,6-dimethylphenyl)-3-[[4-[[5-(trifluoromethoxy)indan-1-ylidene]amino]oxyphenyl]methyleneamino]urea
(12) ##STR00069##
(13) To a solution of 4-[[5-(trifluoromethoxy)indan-1-ylidene]amino]oxybenzaldehyde (1.0 eq., 0.1 g) in methanol (2.9 mL) was added 1-amino-3-(2,6-dimethylphenyl)urea (1.05 eq., 0.056 g) at room temperature. The reaction mixture was then stirred at 65 C. overnight. The resulting white precipitate was filtered, washed twice with methanol and pentane.
(14) Mp=174-176 C. .sup.1H NMR (400 MHz, DMSO-d.sub.6) ppm: 10.44-10.50 (m, 1H), 8.44-8.51 (m, 1H), 7.87-7.92 (m, 2H), 7.80-7.86 (m, 2H), 7.47-7.52 (m, 1H), 7.32-7.38 (m, 1H), 7.24-7.31 (m, 2H), 7.09 (s, 3H), 3.10-3.21 (m, 4H), 2.21 (s, 6H)
Example 2:
Preparation of [([4-[1-[4-(trifluoromethoxy)phenyl]ethylideneamino]oxyphenyl]methyleneamino] N-(2,6-dimethylphenyl)carbamate
(15) ##STR00070##
(16) Step B-1: Preparation of 4-[1-[4-(trifluoromethoxy)phenyl]ethylideneamino]oxybenzonitrile
(17) ##STR00071##
(18) 4-nitrobenzonitrile (1.0 eq., 0.48 g) was added to a mixture of 1-[4-(trifluoromethoxy)phenyl]ethanone oxime (1.0 eq., 0.72 g) and dipotassium carbonate (1.0 eq., 0.45 g) in acetonitrile (16 mL). The reaction mixture was heated at 85 C. and stirred at this temperature until full conversion was observed. The mixture was then allowed to cool down to room temperature before filtering the precipitate. The solid was washed with diethyl ether and then was submitted to column chromatography to give the title compound as a solid.
(19) .sup.1H NMR (400 MHz, CDCl.sub.3) ppm: 7.82 (d, 2H), 7.65 (d, 2H), 7.37 (d, 2H), 7.30 (d, 2H), 2.49 (s, 3H).
(20) Step B-2: Preparation of 4-[1-[4-(trifluoromethoxy)phenyl]ethylideneamino]oxybenzaldehyde
(21) ##STR00072##
(22) To a solution of 4-[1-[3-(trifluoromethoxy)phenyl]ethylideneamino]oxybenzonitrile (1.0 eq., 0.64 g) in dichloromethane (20 mL) was added DIBAL-H (1.0 mol/L) in dichloromethane (1.1 eq., 2.2 mL) at 0 C.
(23) The mixture was stirred at this temperature for 1 h, then quenched by careful addition of water at 0 C. and allowed to warm to room temperature. The aqueous layer was extracted twice with ethyl acetate, the organic phase dried over sodium sulphate and the solvent evaporated. The crude reaction mixture was used without purification in the following step.
(24) Step B-3: Preparation of [1-[4-(trifluoromethoxy)phenyl]ethylideneamino]oxybenzaldehyde oxime
(25) ##STR00073##
(26) To a solution of 4-[1-[4-(trifluoromethoxy)phenyl]ethylideneamino]oxybenzaldehyde (1.0 eq., 0.06 g) in methanol (0.9 mL) were added hydroxylammonium chloride (2.3 eq., 0.02 mL) then sodium acetate trihydrate (2.5 eq., 0.04 g). The reaction mixture was then heated at 70 C. and stirred for 1 h. The mixture was then allowed to cool down to room temperature before filtering the precipitate. The liquid was evaporated and then dissolved in a mixture of ethyl acetate/HCl (1N). The aqueous layer was extracted twice with ethyl acetate, the organic phase dried over sodium sulphate and the solvent evaporated, to afford the title compound as a solid.
(27) .sup.1H NMR (400 MHz, DMSO-d.sub.6) ppm: 8.11 (s, 1H), 7.97 (d, 2H), 7.60 (d, 2H), 7.48 (d, 2H), 7.31 (d, 2H), 2.47 (s, 3H).
(28) Step B-4: Preparation of [1-[4-(trifluoromethoxy)phenyl]ethylideneamino]oxyphenyl]methyleneamino]N-(2,6-dimethylphenyl)carbamate (compound 2)
(29) ##STR00074##
(30) To a solution of 1-[4-(trifluoromethoxy)phenyl]ethylideneamino]oxybenzaldehyde oxime (1.0 eq., 59 mg) in tetrahydrofuran (5.5 mL) was added 2,6-dimethylphenyl-isocyanate (3.0 eq., 79 mg) under argon at room temperature. The reaction mixture was then stirred at 65 C. overnight. The resulting white precipitate was filtered, and then was submitted to column chromatography to give the title compound as a solid. Mp=145-152 C.
(31) 1H NMR (400 MHz, CDCl3) ppm: 8.41-8.48 (m, 1H), 7.83-7.89 (m, 2H), 7.66-7.76 (m, 3H), 7.37-7.43 (m, 2H), 7.31-7.34 (m, 2H), 7.12-7.19 (m, 3H), 2.47-2.54 (m, 3H), 2.33-2.40 (m, 6H).
Example 3:
Preparation of 1-(2,6-dimethylphenyl)-3-[[4-[2-[1-[4-(trifluoromethoxy)phenyl]ethylidene]hydrazino]phenyl]methyleneamino]thiourea
(32) ##STR00075##
(33) Step C-1: Preparation of tert-butyl N-(4-methanehydrazonoylphenyl)carbamate
(34) ##STR00076##
(35) tert-butyl N-(4-formylphenyl)carbamate (1.0 eq., 0.75 g) was added to a solution of hydrazine hydrate (10.0 eq., 4.8 g) in ethanol (34 mL) at 80 C. The resulting mixture was stirred at reflux for 1 h, the allowed to cool down to room temperature. The organic phase dried over sodium sulphate and the solvent evaporated. The crude reaction mixture was used without purification in the following step.
(36) Step C-2: Preparation of tert-butyl N-[4-[[(2,6-dimethylphenyl)carbamothioylhydrazono]methyl]phenyl]carbamate
(37) ##STR00077##
(38) To a solution of 2-isothiocyanato-1,3-dimethyl-benzene (2.8 eq., 1.3 g) in tetrahydrofuran (29 mL) was added tert-butyl N-(4-methanehydrazonoylphenyl)carbamate (1.0 eq., 0.7 g). The reaction mixture was then stirred at 65 C. overnight. The resulting white precipitate was filtered off, the filtrate was evaporated and was then submitted to column chromatography to give the title compound as a solid.
(39) 1H NMR (400 MHz, DMSO-d6) ppm: 11.65 (s, 1H), 9.77 (s, 1H), 9.54 (s, 1H), 8.04 (s, 1H), 7.78 (d, 2H), 7.49 (d, 2H), 7.11 (m, 3H), 2.18 (s, 6H), 1.48 (s, 9H).
(40) Step C-3: Preparation of 1-[(4-aminophenyl)methyleneamino]-3-(2,6-dimethylphenyl)thiourea
(41) ##STR00078##
(42) To a cold solution of tert-butyl N-[4-[[(2,6-dimethylphenyl)carbamothioylhydrazono]methyl]phenyl]carbamate (1.0 eq., 0.55 g) in dichloromethane (7 mL) was added 2,2,2-trifluoroacetic acid (5.0 eq., 0.79 g) at room temperature. The reaction mixture was then stirred overnight at the same temperature. The solvent was evaporated and the resulting mixture was poured into ethyl acetate/water. Sodium hydroxide (1M) was added to the aqueous layer until pH was basic. The aqueous layer was extracted twice with ethyl acetate, the organic phase dried over sodium sulphate and the solvent evaporated. The crude reaction mixture was purified by flash chromatography, to afford the title compound as a solid.
(43) 1H NMR (400 MHz, DMSO-d6) ppm: 11.41 (s, 1H), 9.60 (s, 1H), 7.94 (s, 1H), 7.53 (d, 2H), 7.09 (m, 3H), 6.54 (d, 2H), 5.60 (s, 2H), 2.18 (s, 6H).
(44) Step C-4: Preparation of 1-(2,6-dimethylphenyl)-3-[(4-hydrazinophenyl)methyleneamino]thiourea
(45) ##STR00079##
(46) To solution of 1-[4-aminophenyl)methyleneamino]-3-(2,6-dimethylphenyl)thiourea (1.0 eq., 0.25 g) in concentrated hydrogen chloride (3.1 mL) at 10 C. was added dropwise a solution of sodium nitrite (1.3 aq., 0.07 g) in water (0.3 mL), carefully monitoring that the temperature didn't exceed 5 C. The reaction mixture was stirred for 1 h at 0 C., then cooled down to 40 C. A solution of dichlorotin dihydrate (2.6 eq., 0.49 g) in concentrated hydrogen chloride (0.5 mL) was added dropwise to the reaction mixture, which was then stirred 1 h at 0 C. The mixture was poured into dichloromethane/sodium hydroxide (2M), then sodium hydroxide was added until basic pH. The aqueous layer was extracted twice with ethyl acetate, the organic phase dried over sodium sulphate and the solvent evaporated. The crude reaction mixture was used without purification in the following step.
(47) Step C-5: Preparation of 1-(2,6-dimethylphenyl)-3-[[4-[2-[1-[4-(trifluoromethoxy)phenyl]ethylidene]hydrazino]phenyl]methyleneamino]thiourea (compound 3)
(48) ##STR00080##
(49) To a solution of 1-(2,6-dimethylphenyl)-3-[(4-hydrazinophenyl)methyleneamino]thiourea (1.0 eq., 90 mg) in tetrahydrofuran (2.9 mL) was added 1-[4-(trifluoromethoxy)phenyl]ethanone (1.0 eq., 58 mg) at room temperature. The reaction mixture was then stirred at room temperature overnight. The mixture was poured into dichloromethane/water, the aqueous layer was extracted twice with dichloromethane, the organic phase dried over sodium sulphate and the solvent evaporated. The crude was submitted to column chromatography to give the title compound as an amorphous solid.
(50) 1H NMR (400 MHz, DMSO-d6) ppm: 11.52-11.58 (m, 1H), 9.69-9.73 (m, 1H), 9.62-9.68 (m, 1H), 8.03-8.05 (m, 1H), 7.87-7.94 (m, 2H), 7.72-7.80 (m, 2H), 7.35-7.42 (m, 2H), 7.22-7.29 (m, 2H), 7.08-7.13 (m, 3H), 2.25-2.31 (m, 3H), 2.16-2.20 (m, 6H).
(51) Lc MS Method A: Standard:
(52) Spectra were recorded on a Mass Spectrometer from Waters (SQD or ZQ Single quadrupole mass spectrometer) equipped with an electrospray source (Polarity: positive or negative ions, Capillary: 3.00 kV, Cone range: 30-60 V, Extractor: 2.00 V, Source Temperature: 150 C., Desolvation Temperature: 350 C., Cone Gas Flow: 0 L/Hr, Desolvation Gas Flow: 650 L/Hr, Mass range: 100 to 900 Da) and an Acquity UPLC from Waters: Binary pump, heated column compartment and diode-array detector. Solvent degasser, binary pump, heated column compartment and diode-array detector. Column: Waters UPLC HSS T3, 1.8 Waters UPLC HSS, Temp: 60 C., DAD Wavelength range (nm): 210 to 500, Solvent Gradient: A=water+5% MeOH+0.05% HCOOH, B=Acetonitrile+0.05% HCOOH: gradient: gradient: 0 min 0% B, 100% A; 1.2-1.5 min 100% B; Flow (ml/min) 0.85.
(53) LC MS Method B: Standard Long:
(54) Spectra were recorded on a Mass Spectrometer from Waters (SQD or ZQ Single quadrupole mass spectrometer) equipped with an electrospray source (Polarity: positive or negative ions, Capillary: 3.00 kV, Cone range: 30-60 V, Extractor: 2.00 V, Source Temperature: 150 C., Desolvation Temperature: 350 C., Cone Gas Flow: 0 L/Hr, Desolvation Gas Flow: 650 L/Hr, Mass range: 100 to 900 Da) and an Acquity UPLC from Waters: Binary pump, heated column compartment and diode-array detector. Solvent degasser, binary pump, heated column compartment and diode-array detector. Column: Waters UPLC HSS T3, 1.8 Temp: 60 C., DAD Wavelength range (nm): 210 to 500, Solvent Gradient: A=water+5% MeOH+0.05% HCOOH, B=Acetonitrile+0.05% HCOOH: gradient: gradient: 0 min 0% B, 100% A; 2.7-3.0 min 100% B; Flow (ml/min) 0.85.
(55) LC MS Method C: Unpolar:
(56) Spectra were recorded on a Mass Spectrometer from Waters (SQD or ZQ Single quadrupole mass spectrometer) equipped with an electrospray source (Polarity: positive or negative ions, Capillary: 3.00 kV, Cone range: 30-60 V, Extractor: 2.00 V, Source Temperature: 150 C., Desolvation Temperature: 350 C., Cone Gas Flow: 0 L/Hr, Desolvation Gas Flow: 650 L/Hr, Mass range: 100 to 900 Da) and an Acquity UPLC from Waters: Binary pump, heated column compartment and diode-array detector. Solvent degasser, binary pump, heated column compartment and diode-array detector. Column: Waters UPLC HSS T3, 1.8, Temp: 60 C., DAD Wavelength range (nm): 210 to 500, Solvent Gradient: A=water+5% MeOH+0.05% HCOOH, B=Acetonitrile+0.05% HCOOH: gradient: gradient: 0 min 40% B, 60% A; 1.2-1.5 min 100% B; Flow (ml/min) 0.85.
(57) TABLE-US-00003 TABLE Z Examples of compounds according to any one of embodiments 1 to 22 Ex- Melting ample Point LC MS/ LC MS No. Structures [ C.] NMR Method 1
Biological Examples (%=Percent by Weight, Unless Otherwise Specified)
Example B1:
Spodoptera littoralis (Egyptian Cotton Leaf Worm)
(58) Cotton 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 five L1 larvae. The samples were assessed for mortality, anti-feedant effect, and growth inhibition in comparison to untreated samples 3 days after infestation. Control of Spodoptera littoralis by a test sample is when at least one of mortality, anti-feedant effect, and growth inhibition is higher than the untreated sample.
(59) The following compounds resulted in at least 80% control at an application rate of 200 ppm: 1, 2, 3, 4, 5, 7, 9, 10, 11, 20, 21, 22, 26, 27, 28 and 29.
Example B2:
Plutella xylostella (Diamond Back Moth)
(60) 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.
(61) 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: 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 14, 15, 16, 18, 19, 20, 21, 22, 23, 25, 26, 27, 28 and 29.
Example B3:
Diabrotica balteata (Corn Root Worm)
(62) Maize sprouts, placed on 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.
(63) 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: 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 16, 19, 20, 21, 22, 25, 26, 27, 28, 30 and 31.