Pesticidally active thiophene derivatives

Abstract

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, molluse and nematode pests. ##STR00001##

Claims

1. A compound of formula (I), ##STR00069## wherein Y′ and Y.sup.3 are independently selected from H, halogen, cyano, C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkyl, C.sub.1-C.sub.6-alkoxy, C.sub.1-C.sub.6-haloalkoxy, C.sub.1-C.sub.6-alkoxy-C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-alkylsulfanyl, C.sub.1-C.sub.6-haloalkylsulfanyl, C.sub.1-C.sub.6-alkylsulfinyl, C.sub.1-C.sub.6-haloalkylsulfinyl, C.sub.1-C.sub.6-alkylsulfonyl and C.sub.1-C.sub.6-haloalkyl sulfonyl; Y.sup.5 is -1-CF.sub.3-cyclopropyl; A is CH or N; R.sup.1 is selected from H, C.sub.1-C.sub.6-alkyl, C.sub.2-C.sub.6 alkenyl, C.sub.2-C.sub.6 alkynyl, C.sub.3-C.sub.1 cycloalkyl, C.sub.3-C.sub.1 cycloalkyl, C.sub.1-C.sub.3-alkyl, —C(═O)H, C.sub.1-C.sub.6-alkylcarbonyl, C.sub.3-C.sub.1-cycloalkylcarbonyl, C.sub.1-C.sub.6-alkoxycarbonyl, aryl(C.sub.o-C.sub.3)-alkyl and heteroaryl(C.sub.o-C.sub.3)-alkyl, wherein each of C.sub.1-C.sub.6-alkyl, C.sub.3-C.sub.6 alkenyl, C.sub.3-C.sub.6 alkynyl, C.sub.3-C.sub.1 cycloalkyl, C.sub.3-C.sub.1 cycloalkyl-C.sub.1-C.sub.3-alkyl, C.sub.1-C.sub.6-alkylcarbonyl, C.sub.1-C.sub.6-alkoxycarbonyl, aryl(C.sub.0-C.sub.3)-alkyl and heteroaryl(C.sub.0-C.sub.3)-alkyl is unsubstituted or substituted with 1 to 5 substituents independently selected from halogen, cyano, C.sub.1-C.sub.6-alkoxy and C.sub.1-C.sub.6-alkoxycarbonyl; R.sup.2 is selected from chloro and cyano; Q is H or cyano; or an agrochemically acceptable salt or N-oxide thereof.

2. A compound of formula (I), ##STR00070## wherein Y.sup.1 and Y.sup.3 are independently selected from H, halogen, cyano, C.sub.1-C.sub.6-haloalkyl, C.sub.1-C.sub.6-alkoxy, C.sub.1-C.sub.6-haloalkoxy, C.sub.1-C.sub.6-alkoxy-C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-alkylsulfanyl, C.sub.1-C.sub.6-haloalkylsulfanyl, C.sub.1-C.sub.6-alkylsulfinyl, C.sub.1-C.sub.6-haloalkylsulfinyl, C.sub.1-C.sub.6-alkylsulfonyl and C.sub.1-C.sub.6-haloalkyl sulfonyl; Y.sup.5 is selected from -i-CF(CF.sub.3)(CF.sub.3) and - 1-CF.sub.3-cyclopropyl; A is CH or N; R.sup.1 is selected from H, C.sub.2-C.sub.6 alkenyl, C.sub.2-C.sub.6 alkynyl, C.sub.3-C.sub.1 cycloalkyl, C.sub.3-C.sub.1 cycloalkyl- C.sub.1-C.sub.3-alkyl, —C(═O)H, C.sub.1-C.sub.6-alkylcarbonyl, C.sub.3-C.sub.1-cycloalkylcarbonyl, C1-C6-alkoxycarbonyl, aryl(C.sub.o-C.sub.3)-alkyl and heteroaryl(C.sub.o-C.sub.3)-alkyl, wherein each of C.sub.1-C.sub.6-alkyl, C.sub.3-C.sub.6 alkenyl, C.sub.3-C.sub.6 alkynyl, C.sub.3-C.sub.1 cycloalkyl, C.sub.3-C.sub.1 cycloalkyl- C1-C3-alkyl, C1-C6-alkylcarbonyl, C.sub.1-C.sub.6-alkoxycarbonyl, aryl(C.sub.0-C.sub.3)-alkyl and heteroaryl(C.sub.0-C.sub.3)-alkyl is unsubstituted or substituted with 1 to 5 substituents independently selected from halogen, cyano, C.sub.1-C.sub.6-alkoxy and C.sub.1-C.sub.6-alkoxycarbonyl; R.sup.2 is cyano; Q is H or cyano; or an agrochemically acceptable salt or N-oxide thereof.

3. The compound according to claim 1 wherein Q is cyano.

4. The compound according to claim 1 wherein R.sup.1 is selected from H, methyl, ethyl, —CH.sub.2CH═CH.sub.2, isobutyl, isopropyl, 2,2,2-trifluoroethyl, cyclopropylmethyl, —C(═O)CH.sub.3, —C(═O)CH.sub.2CH.sub.3, —C(═O)cyclopropyl, —C(═O)OCH.sub.3, —C(═O)OCH.sub.2CH.sub.3, —C(═O)CH(CH.sub.3)(CH.sub.3), —CH.sub.2C═CH, —CH.sub.2CN, —CH.sub.2—O—CH.sub.3, —CH.sub.2—O—CH.sub.2—CH.sub.3 and —CH.sub.2-cyclopropyl.

5. The compound according to claim 1 wherein R.sup.1 is selected from H, isobutyl, 2,2,2-trifluoroethyl, cyclopropylmethyl, —C(═O)CH.sub.3, —C(═O)OCH.sub.3,—C(═O)OCH.sub.2CH.sub.3, —C(═O)CH(CH.sub.3)(CH.sub.3), —CH.sub.2—C—CH, —CH.sub.2CN and —CH.sub.2—O—CH.sub.3.

6. The compound according to claim 1 wherein Y.sup.1 and Y.sup.3 are independently selected from chloro, bromo, —CF.sub.3, —CHF.sub.2, —OCF.sub.3, —OCHF.sub.2, methyl, ethyl —SCH.sub.3, —SOCH.sub.3, —S(O).sub.2CH.sub.3 and CN.

7. The compound according to claim 1 wherein Y.sup.1 and Y.sup.3 are independently selected from chloro, bromo, —CF.sub.3, —OCHF.sub.2 and methyl.

8. A compound selected from 2-cyano-N-cyclopropyl-5-[1-[2,6-dichloro-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenyl]pyrazol-4-yl]thiophene-3-carboxamide; 2 chloro N (1 cyanocyclopropyl) 5 [1 [2,6 dichloro 11 [1,2,2,2 tetrafluoro 1 (trifluoromethyl) ethyl]phenyl]pyrazol yl]thiophene 3 carboxamide; 2-cyano-N-cyclopropyl-5-[1-[2,6-dimethyl-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenyl]pyrazol-4-yl]thiophene-3-carboxamide; 2-chloro-5-[1-[2-chloro-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenyl]pyrazol-4-yl]-N-(1-cyanocyclopropyl)thiophene-3-carboxamide; 5- [1- [2-b rom o-6-chloro-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl] phenyl] pyrazo1-4-yl]-2-chloro-N-(1-cyanocyclopropyl)thiophene-3-carboxamide; 5- [1- [2-chloro-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl] phenyl]pyrazol-4-yl]-2-cyano-N-cyclopropyl-thiophene-3-carboxamide; 5- [1- [2-bromo-6-chloro-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl] phenyl]pyrazol-4-yl]-2-chloro-N-cyclopropyl -thiophene-3-carboxamide; 2-chloro-N-(1-cyanocyclopropyl)-5-[1-[2,6-dimethyl-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenyl]pyrazol-4-yl]thiophene-3-carboxamide; 2-cyano-N-cyclopropyl-5- [1-[2,6-dichloro-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenyl]triazol-4-yl]-N-ethyl-thiophene-3-carboxamide; 2-cyano-N-cyclopropyl-5-[1- [2, 6-dichloro-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl] phenyl]triaz01-4-yl]-N-methyl -thiophene-3-carboxamide; 2-cyano-N-cyclopropyl-5-[1- [2, 6-dichloro-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenyl]triazol -4-yl]thiophene-3-carboxamide; 2-chloro-N-(1-cyanocyclopropyl)-5-[1-[2,6-dichloro-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl] phenyl]triazol-4-yl]-N-ethyl -thiophene-3-carb oxamide; 2-chloro-N-(1-cyanocyclopropyl)-5-[1-[2,6-dichloro-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl] phenyl]triazol -4-yl]-N-methyl -thiophene-3-carboxamide; 2-chloro-N-(1-cyanocyclopropyl)-5-[1-[2,6-dichloro-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenyl]triazol-4-yl]thiophene-3-carboxamide; and 2-chloro-N-cyclopropyl-5- [1-[2,6-dichloro-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenyl]triazo11-4-yl]thiophene-3-carboxamide.

9. A pesticidal composition, which comprises at least one compound according to claim 1, or an agrochemically acceptable salt or N-oxide thereof, as active ingredient and at least one auxiliary.

10. The composition according to claim 9, which further comprises one or more other insecticidally, acaricidally, nematicidally and/or fungicidally active agents.

11. A method for controlling pests, which comprises applying a composition according to claim 9 to the pests or their environment.

12. 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.

13. A coated plant propagation material, wherein the coating of the plant propagation material comprises a compound as defined in claim 1.

14. The compound according to claim 2, wherein Q is cyano.

15. The compound according to claim 2, wherein R.sup.1 is selected from H, methyl, ethyl, —CH.sub.2CH═CH.sub.2, isobutyl, isopropyl, 2,2,2-trifluoroethyl, cyclopropylmethyl, —C(═O)CH.sub.3, —C(═O)CH.sub.2CH.sub.3, —C(═O)cyclopropyl, —C(═O)OCH.sub.3, —C(═O)OCH.sub.2CH.sub.3, —C(═O)CH(CH.sub.3)(CH.sub.3), —CH.sub.2C═CH, —CH.sub.2CN, —CH.sub.2—O—CH.sub.3, —CH.sub.2—O—CH.sub.2—CH.sub.3 and —CH.sub.2-cyclopropyl.

16. The compound according to claim 2, wherein R.sup.1 is selected from H, isobutyl, 2,2,2-trifluoroethyl, cyclopropylmethyl, —C(═O)CH.sub.3, —C(═O)OCH.sub.3,—C(═O)OCH.sub.2CH.sub.3—C(═O)CH(CH.sub.3)(CH.sub.3), —CH.sub.2—C—CH, —CH.sub.2CN and —CH.sub.2—O—CH.sub.3.

17. The compound according to claim 2, wherein Y.sup.1 and Y.sup.3 are independently selected from chloro, bromo, —CF.sub.3, —CHF.sub.2, —OCF.sub.3, —OCHF.sub.2, methyl, ethyl, —SCH.sub.3, —SOCH.sub.3, —S(O).sub.2CH.sub.3 and CN.

18. The compound according to claim 2, wherein Y.sup.1 and Y.sup.3 are independently selected from chloro, bromo, —CF.sub.3, —OCHF.sub.2 and methyl.

Description

EXAMPLES

(1) The following compounds according to embodiment 1 may be prepared according to the methods described herein or according to known methods.

(2) Experimental

(3) The following examples are intended to illustrate the invention and are not to be construed as being limitations thereon.

(4) “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.

(5) LC MS Method A: Standard:

(6) 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 μm, 30×2.1 mm, 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.

(7) LC MS Method B: Standard Long:

(8) 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 μm, 30×2.1 mm, 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.

(9) LC MS Method C: Unpolar:

(10) 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 μm, 30×2.1 mm, 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.

Example 1: Preparation of 2-cyano-N-cyclopropyl-5-[1-[2,6-dichloro-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenyl]pyrazol-4-yl]thiophene-3-carboxamide

a) Preparation of 1 ethyl 5-bromo-2-cyano-thiophene-3-carboxylate

(11) ##STR00032##

(12) To a solution of ethyl 2,5-dibromothiophene-3-carboxylate (4 g) in 12 mL DMF were added copper cyanide (1.23 g) and Pd(PPh.sub.3).sub.4 (291 mg) and the reaction mixture was heated to 80° C. for 21 h. The reaction mixture was poured onto 200 mL of a stirred mixture of ethyl acetate/cyclohexane (3:1), the solids were filtered off through a pad of celite and the filtrate was washed three times with a saturated aqueous solution of sodium carbonate then once with brine. The organic phase was dried over sodium sulfate, filtered and concentrated under reduced pressure. The crude product was purified by flash chromatography (silica, cyclohexane/ethyl acetate) to afford the title product as a white solid.

(13) .sup.1H NMR (400 MHz, CDCl.sub.3) δ ppm 1.45 (t, 3H), 4.55 (q, 3H), 7.58 (s, 1H).

(14) LC-MS (Method A): t.sub.R=0.99 min, m/z=260 [M+1], 262 [M+3].

b) Preparation of 5-bromo-2-cyano-thiophene-3-carboxylic acid

(15) ##STR00033##

(16) A solution of ethyl 5-bromo-2-cyano-thiophene-3-carboxylate (0.250 g) in tetrahydrofurane (3.44 ml) and water (0.96 ml) was treated with lithium hydroxide (0.101 g) and was stirred at 20° C. for 2 hours. The reaction mixture was acidified with conc. Aqueous hydrochloric acid and the mixture was extracted with ethyl acetate. The organic layer was washed with water, then with brine and dried over sodium sulfate. Evaporation of the solvent yielded the title compound as a yellow powder that was used without purification for the following step.

(17) .sup.1H-NMR (d6-DMSO, 400 MHz, δ in ppm): 7.71 (s, 1H).

c) Preparation of 5-bromo-2-cyano-N-cyclopropyl-thiophene-3-carboxamide

(18) ##STR00034##

(19) A solution of 5-bromo-2-cyano-thiophene-3-carboxylic acid (0.228 g) in dichloromethane (4.55 ml) was treated with oxalyl chloride (0.231 g) and a catalytic amount of N,N-dimethylformamide. After 0.5 hour, the reaction mixture was concentrated under reduced pressure and the residue was dissolved in tetrahydrofurane (4.5 ml). This solution was slowly added to a solution of cyclopropylamine (0.106 g) in tetrahydrofurane (4.5 ml) under stirring. After 15 hours, the reaction mixture was treated with an aqueous solution of sodium hydrogen carbonate and extracted twice with dichloromethane. The organic phase was dried over sodium sulfate. The crude product was purified by chromatography over silica gel, eluting with a mixture of ethyl acetate-cyclohexane (3:7). Evaporation of the selected fractions left the title compound as a pale yellow solid.

(20) .sup.1H-NMR (CDCl.sub.3, 400 MHz, δ in ppm): 7.48 (s, 1H), 6.50 (br. s, 1H), 2.91 (m, 1H), 0.95-0.87 (m, 2H), 0.72-0.67 (m, 2H).

d) Preparation of [2,6-dichloro-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenyl]hydrazine

(21) ##STR00035##

(22) To a suspension of 2,6-dichloro-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]aniline) (3.3 g) in 15 mL solution of HCl (6N) at 0-5° C. was added dropwise a solution of NaNO.sub.2 (897 mg) in 10 mL water then the solution was stirred for 20 min at 0-5° C. then it was added dropwise at room temperature to the solution of SnCl.sub.2 (5.68 g) in 25 mL aqueous HCl (6N). The precipitate was filtered and washed with water. The resulting wet cake was suspended in water and the pH was adjusted to 10 and the organic material was extracted into ethyl acetate, the organic phase was dried over sodium sulfate, filtered and evaporated. The crude product was purified by flash chromatography (silica, DCM) to afford the title product as a white solid.

(23) .sup.1H NMR (300 MHz, CDCl.sub.3) δ ppm: 4.0-4.1 (brs, 2H), 5.78-5.9 (brs, 1H), 7.47 (s, 2H).

e) Preparation of 1-[2,6-dichloro-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenyl]pyrazole

(24) ##STR00036##

(25) To the a solution of [2,6-dichloro-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenyl]hydrazine (424 mg) in EtOH (1.43 mL) were added tetramethoxypropane (202 mg) and H.sub.2SO.sub.4 (62 mg) and the reaction mixture was heated to 80° C. for 3 h. The reaction mixture was partitioned between ethyl acetate and a saturated solution of NaHCO.sub.3, the layers were separated, the aqueous phase was extracted with ethyl acetate and the combined organic phase was dried over magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by flash chromatography (silica, cyclohexane/gradient of ethyl acetate) to afford the title compound.

(26) .sup.1H NMR (300 MHz, CDCl.sub.3) δ ppm: 6.55 (t, 1H), 7.61 (m, 1H), 7.71 (s, 2H), 7.85 (m, 1H).

f) Preparation of 1-[2,6-dichloro-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenyl]-4-iodo-pyrazole

(27) ##STR00037##

(28) To a solution of 1-[2,6-dichloro-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenyl]pyrazole (1.81 g) in 25 mL acetonitrile was added dropwise a solution of N-iodosuccinimide (5.36 g) in 35 mL acetonitrile over 10 min and the reaction mixture was heated to reflux for 5 h. The reaction mixture was concentrated under reduced pressure then poured onto of a mixture of ethyl acetate/water, the aqueous phase was separated and extracted twice with ethyl acetate. The combined organic phases were washed with a saturated solution of sodium carbonate then brine and dried over sodium sulfate, filtered and concentrated under reduced pressure. The crude product was purified by flash chromatography (silica, cyclohexane/ethyl acetate) to afford the title product as a beige solid.

(29) .sup.1H NMR (300 MHz, CDCl.sub.3) δ ppm 7.64 (s, 1H), 7.71 (m, 2H), 7.83 (s, 1H). mp° C. 92-96° C.

g) Preparation of 1-[2,6-dichloro-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenyl]-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrazole

(30) ##STR00038##

(31) In a microwave tube, 1-[2,6-dichloro-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenyl]-4-iodo-pyrazole (2.23 g), 4,4,5,5-tetramethyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3,2-dioxaborolane (1.11 g) and potassium acetate (1.09 g) were dissolved in 11 ml dimethylsulfoxide. The mixture was purged with argon for 5 min. [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium (66 mg) was added and the mixture was heated to 80° C. for 4 h. The reaction mixture was diluted with ethyl acetate, filtered through a pad of celite, the filtrate was washed with a saturated solution of ammonium chloride and brine. The organic phase was dried over sodium sulfate, filtered and evaporated. The resulting brown oil was progressed to the next step without purification.

(32) LC-MS (Method A): t.sub.R=1.32 min, m/z=508 [M+1].

h) Preparation of ethyl 2-cyano-5-[1-[2,6-dichloro-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenyl]pyrazol-4-yl]thiophene-3-carboxylate

(33) ##STR00039##

(34) In a flask, 1-[2,6-dichloro-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenyl]-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrazole (467 mg), 1 ethyl 5-bromo-2-cyano-thiophene-3-carboxylate (200 mg) were dissolved in 5.4 mL of DMF. The mixture was purged with argon for 5 min then Pd(PPh.sub.3).sub.4 (89 mg) and a solution of potassium carbonate (322 g) in 0.76 mL of water were added and the mixture was heated at 85° C. for 3 h. The reaction mixture was diluted with ethyl acetate, filtered through a pad of celite, the filtrate was washed with water and brine. The organic phase was dried over sodium sulfate, filtered and concentrated under reduced pressure. The crude brown oil was purified by flash chromatography (silica, ethyl acetate/cyclohexane) to afford the tilte compound as an oil.

(35) .sup.1H NMR (400 MHz, CDCl.sub.3) δ ppm 1H NMR (400 MHz, CDCl3) δ ppm 1.45 (t, 3H), 4.45 (q, 2H), 7.62 (s, 1H), 7.78 (s, 2H), 7.9 (s, 1H), 8.1 (s, 1H).

(36) LC-MS (Method A): t.sub.R=1.30 min, m/z=560 [M+1].

i) Preparation of 2-cyano-5-[1-[2,6-dichloro-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenyl]pyrazol-4-yl]thiophene-3-carboxylic acid

(37) ##STR00040##

(38) A mixture of ethyl 2-cyano-5-[1-[2,6-dichloro-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenyl]-pyrazol-4-yl]thiophene-3-carboxylate (220 mg), lithium hydroxide (28 mg), tetrahydrofuran (3.1 mL) and water (0.4 mL) was stirred at room temperature for 3 h. The mixture was acidified with 1 N HCl and the product was extracted with ethyl acetate. The extract was dried over sodium sulfate, filtered and evaporated to afford a white solid.

(39) LC-MS (Method A): t.sub.R=1.15 min, m/z=532 [M+1].

j) Preparation of 2-cyano-N-cyclopropyl-5-[1-[2,6-dichloro-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenyl]pyrazol-4-yl]thiophene-3-carboxamide

(40) ##STR00041##

(41) To a stirred solution of 2-cyano-5-[1-[2,6-dichloro-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenyl]-pyrazol-4-yl]thiophene-3-carboxylic acid (265 mg) in DMF (2 mL) were added HATU (228 mg), cyclopropylamine (33 mg), N,N.diisopropylethylamine (177 mg) and the reaction mixture was stirred at room temperature overnight. The reaction mixture was partitioned between ethyl acetate and a saturated solution of ammonium chloride, the layers were separated and the organic phase was washed with brine, dried over magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by flash chromatography (silica, cyclohexane/gradient of ethyl acetate) to afford a white solid.

(42) .sup.1H NMR (400 MHz, CDCl.sub.3) δ ppm 1H NMR (400 MHz, CDCl3) δ ppm: 0.69-0.73 (m, 2H), 0.90-0.98 (m, 2H), 2.9-3.0 (m, 1H), 6.6 (brs, 1H), 7.58 (s, 1H), 7.78 (s, 2H), 7.90 (s, 1H), 8.08 (s, 1H). .sup.19F NMR (376 MHz, CDCl.sub.3) δ ppm −182 (m, 1F), −75 (m, 6F).

(43) LC-MS (Method A): t.sub.R=1.18 min, m/z=571 [M+1].

Example 2: Preparation of 2-chloro-N-cyclopropyl-5-[1-[2,6-dichloro-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenyl]pyrazol-4-yl]thiophene-3-carboxamide

a) Preparation of 2-chloro-5-[1-[2,6-dichloro-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenyl]pyrazol-4-yl]thiophene-3-carboxylic acid

(44) ##STR00042##

(45) In a flask, 1-[2,6-dichloro-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenyl]-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrazole (892 mg), 5-bromo-2-chloro-thiophene-3-carboxylic acid (200 mg) were dissolved in 4.9 mL of DMF. The mixture was purged with argon for 5 min. Pd(PPh.sub.3).sub.4 (96 mg) and a solution of potassium carbonate (347 mg) in 1.0 mL of water were added and the mixture was heated at 80° C. for 3 h. The mixture was diluted with ethyl acetate and poured onto a solution of HCl 0.5 M, the mixture was extracted with ethyl acetate. The combined organic layers were dried over sodium sulfate, filtered and evaporated. The crude was redissolved in DCM and extracted with an aqueous solution of NaOH (0.5 M), the combined basic water phase was acidified to pH=2 with an aqueous solution of HCl (6N) and extracted with ethyl acetate three times. The combined organic phases were dried over sodium sulfate, filtrated and evaporated to give the title product as a beige solid.

(46) LC-MS (Method A): t.sub.R=1.21 min, m/z=539 [M−1], 541 [M+1].

b) Preparation of 2-chloro-N-cyclopropyl-5-[1-[2,6-dichloro-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenyl]pyrazol-4-yl]thiophene-3-carboxamide

(47) ##STR00043##

(48) To a stirred solution of 2-chloro-5-[1-[2,6-dichloro-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)-ethyl]phenyl]pyrazol-4-yl]thiophene-3-carboxylic acid (175 mg) in DMF (1.2 mL) were added HATU (164 mg), cyclopropylamine (24 mg), N,N.diisopropylethylamine (127 mg) and the reaction mixture was stirred at room temperature for 2 h. The reaction mixture was partitioned between ethyl acetate and a saturated solution of ammonium chloride, the layers were separated and the organic phase was washed with brine, dried over magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by flash chromatography (silica, cyclohexane/gradient of ethyl acetate) to afford the title compound as a white solid.

(49) 1H NMR (400 MHz, CDCl3) δ ppm: 0.60-0.70 (m, 2H), 0.85-0.95 (m, 2H), 3.88-3.98 (m, 1H), 6.63 (brs, 1H), 7.48 (s, 1H), 7.75 (s, 2H), 7.77 (s, 1H), 7.98 (s, 1H).

(50) .sup.19F NMR (376 MHz, CDCl.sub.3) δ ppm −181.6 (m, 1F), −74.5 (m, 6F).

(51) LC-MS (Method A): t.sub.R=1.18 min, m/z=571 [M+1].

Example 16: Preparation of 2-chloro-N-(1-cyanocyclopropyl)-5-[1-[2,6-dichloro-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenyl]triazol-4-yl]thiophene-3-carboxamide

a) Preparation of 2-azido-1,3-dichloro-5-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]benzene

(52) ##STR00044##

(53) To a stirred solution of con.HCl (80 mL) and H.sub.2O (40 mL), 2,6-dichloro-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]aniline (5.00 g) was added followed by NaNO.sub.2 (1.00 g) at 0° C. The reaction mixture was stirred for 10 min, .sup.tBuOH (40 mL) and NaN.sub.3 (1.5 g) were added and the whole was stirred for 18 h. The aqueous layer was extracted twice with ethyl acetate (200 ml).The combined organic phases were dried over sodium sulfate and concentrated. The residue was purified by column chromatography (PE: EA=10:1) to afford the title compound (4 g) .sup.1H NMR (400 MHz, cdcl.sub.3) δ 7.53 (s, 2H).

b) Preparation of ethyl 2-chloro-5-[1-[2,6-dichloro-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenyl]triazol-4-yl]thiophene-3-carboxylate

(54) ##STR00045##

(55) To a stirred solution of THF (20 mL) and H.sub.2O (10 mL), 2-azido-1,3-dichloro-5-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]benzene (1.78 g) and ethyl 2-chloro-5-ethynyl-thiophene-3-carboxylate (1.07 g), CuSO.sub.4.5H.sub.2O (100 mg), L-ascorbic acid sodium salt (198 mg) were added at room temperature. The mixture was stirred for 18 h at room temperature. The crude mixture was diluted with ethyl acetate and washed with water and brine, dried over magnesium sulfate and evaporated. The residue was purified by column chromatography on silica gel (PE/EA=4:1) to give title compound (1.54 g) .sup.1H NMR (400 MHz, CDCl.sub.3) δ 7.92 (s, 1H), 7.79 (s, 2H), 7.67 (s, 1H), 4.37 (d, J=7.1 Hz, 2H), 1.40 (t, J=6.9 Hz, 3H).

c) Preparation of 2-chloro-5-[1-[2,6-dichloro-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenyl]triazol-4-yl]thiophene-3-carboxylic acid

(56) ##STR00046##
To a solution of ethyl 2-chloro-5-[1-[2,6-dichloro-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenyl]triazol-4-yl]thiophene-3-carboxylate (1.54 g) in EtOH (10 ml) was added NaOH (220 mg) and water (1 ml). The mixture was stirred for 2 h at room temperature and then acidified with 1 N HCl. The mixture was extracted with dichloromethane. The extract was dried over magnesium sulfate and evaporated to afford title compound as a yellow solid.

d) Preparation of example 16: 2-chloro-N-(1-cyanocyclopropyl)-5-[1-[2,6-dichloro-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenyl]triazol-4-yl]thiophene-3-carboxamide

(57) ##STR00047##

(58) To a solution of 2-chloro-5-[1-[2,6-dichloro-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenyl]triazol-4-yl]thiophene-3-carboxylic acid (100 mg) in 3 ml of DMF was added 1-aminocyclopropanecarbonitrile hydrochloride (50 mg), HATU (110 mg) and DIPEA (100 mg) and the reaction mixture was stirred at room temperature overnight and then poured into water (50 mL). The aqueous solution was then extracted 3 times with ethyl acetate (150 mL), the combined organic phases were washed twice with brine (200 mL) before being dried on magnesium sulfate, filtered and concentrated. The residue was purified by flash chromatography on silica gel using PE/EA(4:1) as eluent to afford title compound (65 mg).

(59) .sup.1H NMR (400 MHz, DMSO-d6) δ 9.32 (s, 1H), 9.04(s, 1H), 8.18 (s, 2H),7.71 (s, 1H), 1.56(s, 2H),1.26(s, 2H).

(60) .sup.19F NMR (283 MHz, CDCl.sub.3) δ −82.60(d, 6F, J=7.2 Hz), −188.46 (s, 1F).

Example 14: Preparation of 2-chloro-N-(1-cyanocyclopropyl)-5-[1-[2,6-dichloro-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenyl]triazol-4-yl]thiophene-3-carboxamide

(61) ##STR00048##

(62) To a solution of 2-chloro-N-(1-cyanocyclopropyl)-5-[1-[2,6-dichloro-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenyl]triazol-4-yl]thiophene-3-carboxamide (60.0 mg) and Cs.sub.2CO.sub.3 (80 mg) in DMF (0.5 mL) was added iodoethane (60 mg) at room temperature. The mixture was stirred at 50° C. for 1 h, and then diluted with ethyl acetate. The organic layer was washed with water and brine, dried over Na.sub.2SO.sub.4 and concentrated. The residue was further purified by column chromatography eluting with PE:EA=2:1 to give title product (30 mg).

(63) .sup.1H NMR (400 MHz, DMSO-d.sup.6) δ9.04(s, 1H), 8.18 (s, 2H),7.62 (s, 1H), 3.42 (s, 2H) 1.65(s, 3H),1.43(s, 2H),1.21(s, 2H).

(64) .sup.19F NMR (283 MHz, CDCl.sub.3) δ −82.55(d, 6F, J=7.2 Hz), −188.39(s, 1F).

(65) Preparation of Intermediates:

Preparation of 2-cyano-N-cyclopropyl-5-(2-trimethylsilylethynyl)thiophene-3-carboxamide

(66) ##STR00049##

(67) To a solution of 5-bromo-2-cyano-N-cyclopropyl-thiophene-3-carboxamide (1.49 g) in tetrahydrofurane (38.5 ml), under inert atmosphere, was added N,N-diisopropylethylamine (0.952 g), then cuprous iodide (0.053 g), bis-triphenylphosphine palladium dichloride (0.197 g) and trimethylsilylacetylene (0.826 g).The reaction mixture was stirred for 18 hours at 20° C., at which time, LC-MS analysis showed that the starting material was consumed. The reaction mixture was diluted with ethyl acetate and washed three times with water, then with brine and dried over sodium sulfate. The crude product was purified by chromatography over silica gel, eluting with a mixture of ethyl acetate-cyclohexane. Evaporation of the selected fractions delivered the title compound.

(68) .sup.1H-NMR (CDCl.sub.3, 400 MHz, δ in ppm): 7.50 (s, 1H), 6.46 (br. s, 1H), 2.91 (m, 1H), 0.94-0.87 (m, 2H), 0.71-0.65 (m, 2H), 0.28 (s, 9H).

Preparation of 2-cyano-N-cyclopropyl-5-ethynyl-thiophene-3-carboxamide

(69) ##STR00050##

(70) A solution of 2-cyano-N-cyclopropyl-5-(2-trimethylsilylethynyl)thiophene-3-carboxamide (described above) (1.36 g) in tetrahydrofurane (47 ml), cooled at 0° C., under inert atmosphere, was treated dropwise with a solution of tetrabutylammonium fluoride (1 M in tetrahydrofurane) (9.48 ml). After 20 minutes, LC-MS analysis showed the consumption of the starting material. The reaction was poured into water and the resulting mixture was extracted three times with ethyl acetate. The combined organic layers were washed with brine and dried over sodium sulfate. After removal of the solvent under reduced pressure, the crude product was submitted to chromatography over silica gel, eluting with a mixture of ethyl acetate and cyclohexane. Evaporation of the selected fractions delivered the title compound.

(71) .sup.1H-NMR (CDCl.sub.3, 400 MHz, δ in ppm): 7.58 (s, 1H), 6.51 (br. s, 1H), 3.57 (s, 1H), 2.92 (m, 1H), 0.96-0.85 (m, 2H), 0.75-0.62 (m, 2H).

Preparation of methyl 2-chloro-5-iodo-thiophene-3-carboxylate

(72) ##STR00051##

(73) To a solution of 1.7 g of methyl 2-chlorothiophene-3-carboxylate and 0.1 g of HClO.sub.4 in 20 mL of CH.sub.3CN was added 2.3 g of NIS. The reaction was stirred at room temperature for 6 h then stirred at 50° C. for 24 h. Then the reaction mixture was poured into water and extracted with ethyl acetate three times. The combined organic layers were dried over sodium sulfate, filtered and concentrated under vacuum to give 2.2 g of the title compound.

(74) .sup.1HNMR (400 MHz, d.sub.6-DMSO): δ (ppm) 7.55 (s, 1H), 3.77 (s, 3H).

Preparation of methyl 2-chloro-5-(2-trimethylsilylethynyl)thiophene-3-carboxylate

(75) ##STR00052##

(76) To a 5 mL dry solution of Et.sub.3N solution was successively added 1.2 g of methyl 2-chloro-5-iodo-thiophene-3-carboxylate, 400 mg of ethynyl(trimethyl)silane, 28 mg of PdCl.sub.2(PPh.sub.3).sub.2 38 mg of CuI under a N.sub.2 atmosphere. The mixture was heated at 70° C. for 2 h. After cooling the mixture to room temperature, EtOAc was added and the suspension was filtered through a Celite pad. The filtrate was collected and evaporated under reduced pressure. The residue was purified by column chromatography on silica gel (petroleum ether/ethyl acetate=2:1) to give 1.2 g of title compound.

(77) .sup.1HNMR (400 MHz, CDCl.sub.3): δ (ppm) 7.43 (s, 1H), 3.87 (s, 3H), 0.25 (s, 9H).

methyl 2-chloro-5-ethynyl-thiophene-3-carboxylate

(78) ##STR00053##

(79) To a solution of 1.3 g of methyl 2-chloro-5-(2-trimethylsilylethynyl)thiophene-3-carboxylate in 50 mL of THF (50 mL), 10 mL of tetrabutylammonium fluoride (1M solution in THF) was added dropwise at room temperature. The reaction mixture was stirred at room temperature for 0.5 h. Then the reaction mixture was poured into water and extracted with ethyl acetate three times. The combined organic layers were dried over sodium sulfate, filtered and concentrated under vacuum to give 0.8 g of title product which was used without further purification.

Preparation of 2,5-dibromo-N-cyclopropyl-thiophene-3-carboxamide

(80) ##STR00054##

(81) A solution of 5-bromo-2-cyano-thiophene-3-carboxylic acid (2.0 g) in dichloromethane (34.97 ml) was treated with oxalyl chloride (1.77 g) and a catalytic amount of N,N-dimethylformamide at room temperature. After 1.5 hour, the reaction mixture was concentrated under reduced pressure and the residue was dissolved in tetrahydrofuran (35 mL). This solution was slowly added to a solution of cyclopropylamine (815 mg) in tetrahydrofuran (35 mL) under stirring. After 1 hour, the reaction mixture was treated with an aqueous solution of sodium bicarbonate and extracted twice with dichloromethane. The organic phase was dried over sodium sulfate. The crude product was purified by chromatography over silica gel, eluting with a mixture of ethyl acetate-cyclohexane (2:8). Evaporation of the selected fractions left the title compound as a white powder.

(82) .sup.1H-NMR (CDCl.sub.3, 400 MHz, δ in ppm): 0.58-0.68 (m, 2H), 0.80-0.92 (m, 2H), 2.82-2.91 (m, 1H), 6.5 (brs, 1H), 7.32 (s, 1H).

Preparation of 5-bromo-2-cyano-N-cyclopropyl-thiophene-3-carboxamide

(83) ##STR00055##

(84) A solution of 5-bromo-2-cyano-thiophene-3-carboxylic acid (221 mg g) in dichloromethane (7.62 ml) was added 1-amino-1-cyclopropanecarbonitrile hydrochloride (124 mg), triethylamine (292 mg), HOAT (146 mg) and EDC hydrochloride (205 mg) and the reaction mixture was stirred at room temperature for 17 h. The reaction mixture was concentrated under vacuum and the residue was purified by chromatography over silica gel, eluting with a mixture of ethyl acetate-cyclohexane. Evaporation of the selected fractions left the title compound as a yellow solid.

(85) .sup.1H-NMR (DMSO, 400 MHz, δ in ppm): 1.28-1.32 (m, 2H), 1.58-1.62 (m, 2H), 7.8 (s, 1H), 9.5 (s, 1H).

(86) The following compounds which have been characterized were prepared in analogy to Example 1, 2, 14 and 16.

(87) TABLE-US-00004 TABLE 1 Examples of compounds of formula (I): Ex. Structure .sup.1H-NMR (400 MHz) .sup.19F NMR 3 (CDCl.sub.3) δ ppm: 1.42- 1.48 (m, 2H), 1.70-1.75 (m, 2H), 6.94 (brs, 1H), 7.63 (s, 1H), 7.78 (s, 2H), 7.91 (s, 1H), 8.08 (s, 1H) (377 MHz, CDCl.sub.3) δ ppm −181.5 (m, 1F), −75.18 (m, 6F) 4 (CDCl.sub.3) δ ppm: 1.38- 1.43 (m, 2H), 1.58-1.62 (m, 2H), 7.02 (brs, 1H), 7.50 (s, 1H), 7.76 (s, 2H), 7.79 (s, 1H), 7.99 (s, 1H) (377 MHz, CDCl.sub.3) δ ppm −181.6 (m, 1F), −75.2 (m, 6F) 5 (CDCl3) δ ppm 8.05- 7.99 (m, 1 H) 7.83-7.78 (m, 1 H) 7.59-7.53 (m, 1 H) 7.47-7.40 (m, 2 H) 6.58-6.49 (m, 1 H) 3.01- 2.91 (m, 1 H) 2.16 (s, 6 H) 0.99-0.89 (m, 2 H) 0.77-0.68 (m, 2 H) (377 MHz, CDCl3) δ ppm −75.43 (s, 6 F) −181.92 (s, 1 F) 6 (CDCl3) δ ppm 8.22- 8.15 (m, 1 H) 7.96-7.90 (m, 1 H) 7.88-7.81 (m, 2 H) 7.71-7.65 (m, 1 H) 7.53-7.46 (m, 1 H) 7.11- 7.01 (m, 1 H) 1.75- 1.66 (m, 2 H) 1.44-1.36 (m, 2 H) (377 MHz, CDCl3) δ ppm −75.44 (s, 6 F) −182.02 (s, 1 F) 7 0 (CDCl3) δ ppm 8.00- 7.97 (m, 1 H) 7.94-7.89 (m, 1 H) 7.82-7.76 (m, 2 H) 7.52-7.48 (m, 1 H) 7.09-7.03 (m, 1 H) 1.73- 1.66 (m, 2 H) 1.44- 1.37 (m, 2H) (377 MHz, CDCl3) δ ppm −75.18 (s, 6 F) −182.02(s, 1 F) 8 (CDCl3) δ ppm 8.31- 8.27 (m, 1 H) 8.02-7.99 (m, 1 H) 7.86-7.81 (m, 2 H) 7.71-7.66 (m, 1 H) 7.59-7.56 (m, 1 H) 6.56- 6.49 (m, 1 H) 2.99- 2.89 (m, 1 H) 0.97-0.90 (m, 2 H) 0.75-0.67 (m, 2 H) (377 MHz, CDCl3) δ ppm −75.43 (s, 6 F) −181.86(s, 1 F) 9 (CDCl3) δ ppm 8.08- 8.05 (m, 1 H) 7.92-7.88 (m, 2 H) 7.81-7.77 (m, 1 H) 7.60-7.56 (m, 1 H) 6.59-6.52 (m, 1 H) 2.98- 2.91 (m, 1 H) 0.97- 0.89 (m, 2 H) 0.75-0.68 (m, 2 H) (377 MHz, CDCl3) δ ppm −75.18 (s, 6 F) −181.54(s, 1 F) 10 (CDCl3) δ ppm 7.95- 7.88 (m, 1 H) 7.71-7.65 (m, 1 H) 7.48-7.45 (m, 1 H) 7.45-7.39 (m, 2 H) 7.10-7.03 (m, 1 H) 2.16 (s, 6 H) 1.73-1.67 (m, 2 H) 1.44 1.36 (m, 2 H) (377 MHz, CDCl3) δ ppm −75.45 (s, 6 F) −181.22(s, 1 F) 11 (DMSO-D6) δ ppm 9.24 (s, 1H), 8.22 (s, 2H), 7.92 (s, 1H), 3.53 (s, 2H), 2.94 (s, 1H), 1.22 (s, 3H), 0.69 (s, 2H), 0.58 (s, 2H). (283 MHz, CDCl.sub.3) δ ppm −82.80 (d, 6F, J = 7.2 Hz), −188.64 (s, 1F) 12 (DMSO-D6) δ ppm 9.23 (s, 1H), 8.21 (s, 2H), 7.94 (s, 1H), 3.03 (s, 3H), 2.94 (s, 1H), 0.66 (s, 2H), 0.58 (s, 2H). (283 MHz, CDCl.sub.3) δ ppm −82.80 (d, 6F, J = 7.2 Hz), −188.61 (s, 1F). 13 (DMSO-D6) δ ppm 9.21 (s, 1H), 8.80 (s, 1H), 8.22 (s, 2H), 8.04 (s, 1H), 2.87 (s, 1H), 0.75 (d, J = 6.7 Hz, 2H), 0.60 (s, 2H). (283 MHz, CDCl.sub.3) δ ppm −82.61 (d, 6F, J = 7.2 Hz), −188.44 (s, 1F). 15 (DMSO-D6) δ ppm 9.03(s, 1H), 8.17 (s, 2H), 7.59 (s, 1H), 3.02 (s, 3H) 1.42(s, 2H), 1.21(s, 2H). (283 MHz, CDCl.sub.3) δ ppm −82.60(d, 6F, J = 7.2 Hz), −188.45 (s, 1F). 17 (DMSO-D6) δ ppm 9.03 (s, 1H), 8.44(s, 1H), 8.18 (s, 2H), 7.63 (s, 1H), 2.80 (s, 1H), 0.67- 0.69(d, J = 6.7 Hz, 2H), 0.53 (s, 2H) (283 MHz, CDCl.sub.3) δ ppm −82.47(d, 6F, J = 7.2 Hz), −188.33 (s, 1F).

Formulation Examples (%=Percent by Weight)

Example F1

(88) TABLE-US-00005 Emulsion concentrates a) b) c) Active ingredient 25% 40% 50% Calcium dodecylbenzenesulfonate  5%  8%  6% Castor oil polyethylene  5% — — glycol ether (36 mol of EO) Tributylphenoxypolyethylene — 12%  4% glycol ether (30 mol of EO) Cyclohexanone — 15% 20% Xylene mixture 65% 25% 20%

(89) Emulsions of any desired concentration can be prepared from such concentrates by dilution with water.

Example F2

(90) TABLE-US-00006 Solutions a) b) c) d) Active ingredient 80% 10% 5% 95% Ethylene glycol monomethyl 20% — — — ether Polyethylene glycol — 70% — — MW 400 N-Methylpyrrolid-2-one — 20% — — Epoxidized coconut oil — — 1%  5% Petroleum ether — — 94%  — (boiling range: 160-190°)

(91) The solutions are suitable for use in the form of microdrops.

Example F3

(92) TABLE-US-00007 Granules a) b) c) d) Active ingredient 5% 10%  8% 21% Kaolin 94%  — 79% 54% Highly disperse silica 1% — 13%  7% Attapulgite — 90% — 18%

(93) The active ingredient is dissolved in dichloromethane, the solution is sprayed onto the carrier(s), and the solvent is subsequently evaporated in vacuo.

Example F4

(94) TABLE-US-00008 Dusts a) b) Active ingredient 2% 5% Highly disperse silica 1% 5% Talc 97%  — Kaolin — 90% 

(95) Ready-to-use dusts are obtained by intimately mixing the carriers and the active ingredient.

Example F5

(96) TABLE-US-00009 Wettable powders a) b) c) Active ingredient 25%  50% 75% Sodium lignosulfonate 5%  5% — Sodium lauryl sulfate 3% —  5% Sodium diisobutyl- —  6% 10% naphthalenesulfonate Octylphenoxypolyethylene —  2% — glycol ether (7-8 mol of EO) Highly disperse silica 5% 10% 10% Kaolin 62%  27% —

(97) The active ingredient is mixed with the additives and the mixture is ground thoroughly in a suitable mill. This gives wettable powders, which can be diluted with water to give suspensions of any desired concentration.

Example F6

(98) TABLE-US-00010 Extruder granules Active ingredient 10% Sodium lignosulfonate  2% Carboxymethylcellulose  1% Kaolin 87%

(99) The active ingredient is mixed with the additives, and the mixture is ground, moistened with water, extruded, granulated and dried in a stream of air.

Example F7

(100) TABLE-US-00011 Coated granules Active ingredient 3% Polyethylene glycol (MW 200) 3% Kaolin 94% 

(101) In a mixer, the finely ground active ingredient is applied uniformly to the kaolin, which has been moistened with the polyethylene glycol. This gives dust-free coated granules.

Example F8

(102) TABLE-US-00012 Suspension concentrate Active ingredient 40% Ethylene glycol 10% Nonylphenoxypolyethylene glycol ether (15 mol of EO)  6% Sodium lignosulfonate 10% Carboxymethylcellulose  1% 37% aqueous formaldehyde solution 0.2%  Silicone oil (75% aqueous emulsion) 0.8%  Water 32%

(103) The finely ground active ingredient is mixed intimately with the additives. Suspensions of any desired concentration can be prepared from the thus resulting suspension concentrate by dilution with water.

Example F9

(104) TABLE-US-00013 Powders for dry seed treatment a) b) c) active ingredient 25% 50% 75% light mineral oil  5%  5%  5% highly dispersed silicic acid  5%  5% — Kaolin 65% 40% — Talcum — — 20%

(105) The combination is thoroughly mixed with the adjuvants and the mixture is thoroughly ground in a suitable mill, affording powders that can be used directly for seed treatment.

Example F10

(106) TABLE-US-00014 Emulsifiable concentrate active ingredient 10% octylphenol polyethylene glycol ether  3% (4-5 mol of ethylene oxide) calcium dodecylbenzenesulfonate  3% castor oil polyglycol ether (35 mol of ethylene oxide)  4% Cyclohexanone 30% xylene mixture 50%

(107) Emulsions of any required dilution, which can be used in plant protection, can be obtained from this concentrate by dilution with water.

Example F11

(108) TABLE-US-00015 Flowable concentrate for seed treatment active ingredients 40%  propylene glycol 5% copolymer butanol PO/EO 2% Tristyrenephenole with 10-20 moles EO 2% 1,2-benzisothiazolin-3-one (in the form of a 20% solution in 0.5%.sup.  water) monoazo-pigment calcium salt 5% Silicone oil (in the form of a 75% emulsion in water) 0.2%.sup.  Water 45.3%  

(109) The finely ground combination is intimately mixed with the adjuvants, giving a suspension concentrate from which suspensions of any desired dilution can be obtained by dilution with water. Using such dilutions, living plants as well as plant propagation material can be treated and protected against infestation by microorganisms, by spraying, pouring or immersion.

(110) The activity of the compositions according to the invention can be broadened considerably, and adapted to prevailing circumstances, by adding other insecticidally, acaricidally and/or fungicidally active ingredients. The mixtures of the compounds according to any one of embodiments 1 to 12 with other insecticidally, acaricidally and/or fungicidally active ingredients may also have further surprising advantages which can also be described, in a wider sense, as synergistic activity. For example, better tolerance by plants, reduced phytotoxicity, insects can be controlled in their different development stages or better behaviour during their production, for example during grinding or mixing, during their storage or during their use.

(111) Suitable additions to active ingredients here are, for example, representatives of the following classes of active ingredients: organophosphorus compounds, nitrophenol derivatives, thioureas, juvenile hormones, formamidines, benzophenone derivatives, ureas, pyrrole derivatives, carbamates, pyrethroids, chlorinated hydrocarbons, acylureas, pyridylmethyleneamino derivatives, macrolides, neonicotinoids and Bacillus thuringiensis preparations.

(112) The following mixtures of the compounds according to any one of embodiments 1 to 12 with active ingredients are preferred (the abbreviation “TX” means “one compound selected from the compounds according to any one of embodiments 1 to 12, preferably one compound from embodiment 12):

(113) an adjuvant selected from the group of substances consisting of petroleum oils (alternative name) (628)+TX, an acaricide selected from the group of substances consisting of 1,1-bis(4-chlorophenyl)-2-ethoxyethanol (IUPAC name) (910)+TX, 2,4-dichlorophenyl benzenesulfonate (IUPAC/Chemical Abstracts name) (1059)+TX, 2-fluoro-N-methyl-N-1-naphthylacetamide (IUPAC name) (1295)+TX, 4-chlorophenyl phenyl sulfone (IUPAC name) (981)+TX, abamectin (1)+TX, acequinocyl (3)+TX, acetoprole [CCN]+TX, acrinathrin (9)+TX, aldicarb (16)+TX, aldoxycarb (863)+TX, alpha-cypermethrin (202)+TX, amidithion (870)+TX, amidoflumet [CCN]+TX, amidothioate (872)+TX, amiton (875)+TX, amiton hydrogen oxalate (875)+TX, amitraz (24)+TX, aramite (881)+TX, arsenous oxide (882)+TX, AVI 382 (compound code)+TX, AZ 60541 (compound code)+TX, azinphos-ethyl (44)+TX, azinphos-methyl (45)+TX, azobenzene (IUPAC name) (888)+TX, azocyclotin (46)+TX, azothoate (889)+TX, benomyl (62)+TX, benoxafos (alternative name) [CCN]+TX, benzoximate (71)+TX, benzyl benzoate (IUPAC name) [CCN]+TX, bifenazate (74)+TX, bifenthrin (76)+TX, binapacryl (907)+TX, brofenvalerate (alternative name)+TX, bromo-cyclen (918)+TX, bromophos (920)+TX, bromophos-ethyl (921)+TX, bromopropylate (94)+TX, buprofezin (99)+TX, butocarboxim (103)+TX, butoxycarboxim (104)+TX, butylpyridaben (alternative name)+TX, calcium polysulfide (IUPAC name) (111)+TX, camphechlor (941)+TX, carbanolate (943)+TX, carbaryl (115)+TX, carbofuran (118)+TX, carbophenothion (947)+TX, CGA 50′439 (development code) (125)+TX, chinomethionat (126)+TX, chlorbenside (959)+TX, chlordimeform (964)+TX, chlordimeform hydrochloride (964)+TX, chlorfenapyr (130)+TX, chlorfenethol (968)+TX, chlorfenson (970)+TX, chlorfensulfide (971)+TX, chlorfenvinphos (131)+TX, chlorobenzilate (975)+TX, chloromebuform (977)+TX, chloromethiuron (978)+TX, chloropropylate (983)+TX, chlorpyrifos (145)+TX, chlorpyrifos-methyl (146)+TX, chlorthiophos (994)+TX, cinerin I (696)+TX, cinerin II (696)+TX, cinerins (696)+TX, clofentezine (158)+TX, closantel (alternative name) [CCN]+TX, coumaphos (174)+TX, crotamiton (alternative name) [CCN]+TX, crotoxyphos (1010)+TX, cufraneb (1013)+TX, cyanthoate (1020)+TX, cyflumetofen (CAS Reg. No.: 400882-07-7)+TX, cyhalothrin (196)+TX, cyhexatin (199)+TX, cypermethrin (201)+TX, DCPM (1032)+TX, DDT (219)+TX, demephion (1037)+TX, demephion-O (1037)+TX, demephion-S (1037)+TX, demeton (1038)+TX, demeton-methyl (224)+TX, demeton-O (1038)+TX, demeton-O-methyl (224)+TX, demeton-S (1038)+TX, demeton-S-methyl (224)+TX, demeton-S-methylsulfon (1039)+TX, diafenthiuron (226)+TX, dialifos (1042)+TX, diazinon (227)+TX, dichlofluanid (230)+TX, dichlorvos (236)+TX, dicliphos (alternative name)+TX, dicofol (242)+TX, dicrotophos (243)+TX, dienochlor (1071)+TX, dimefox (1081)+TX, dimethoate (262)+TX, dinactin (alternative name) (653)+TX, dinex (1089)+TX, dinex-diclexine (1089)+TX, dinobuton (269)+TX, dinocap (270)+TX, dinocap-4 [CCN]+TX, dinocap-6 [CCN]+TX, dinocton (1090)+TX, dinopenton (1092)+TX, dinosulfon (1097)+TX, dinoterbon (1098)+TX, dioxathion (1102)+TX, diphenyl sulfone (IUPAC name) (1103)+TX, disulfiram (alternative name) [CCN]+TX, disulfoton (278)+TX, DNOC (282)+TX, dofenapyn (1113)+TX, doramectin (alternative name) [CCN]+TX, endosulfan (294)+TX, endothion (1121)+TX, EPN (297)+TX, eprinomectin (alternative name) [CCN]+TX, ethion (309)+TX, ethoate-methyl (1134)+TX, etoxazole (320)+TX, etrimfos (1142)+TX, fenazaflor (1147)+TX, fenazaquin (328)+TX, fenbutatin oxide (330)+TX, fenothiocarb (337)+TX, fenpropathrin (342)+TX, fenpyrad (alternative name)+TX, fenpyroximate (345)+TX, fenson (1157)+TX, fentrifanil (1161)+TX, fenvalerate (349)+TX, fipronil (354)+TX, fluacrypyrim (360)+TX, fluazuron (1166)+TX, flubenzimine (1167)+TX, flucycloxuron (366)+TX, flucythrinate (367)+TX, fluenetil (1169)+TX, flufenoxuron (370)+TX, flumethrin (372)+TX, fluorbenside (1174)+TX, fluvalinate (1184)+TX, FMC 1137 (development code) (1185)+TX, formetanate (405)+TX, formetanate hydrochloride (405)+TX, formothion (1192)+TX, formparanate (1193)+TX, gamma-HCH (430)+TX, glyodin (1205)+TX, halfenprox (424)+TX, heptenophos (432)+TX, hexadecyl cyclopropanecarboxylate (IUPAC/Chemical Abstracts name) (1216)+TX, hexythiazox (441)+TX, iodomethane (IUPAC name) (542)+TX, isocarbophos (alternative name) (473)+TX, isopropyl O-(methoxyaminothiophosphoryl)salicylate (IUPAC name) (473)+TX, ivermectin (alternative name) [CCN]+TX, jasmolin I (696)+TX, jasmolin II (696)+TX, jodfenphos (1248)+TX, lindane (430)+TX, lufenuron (490)+TX, malathion (492)+TX, malonoben (1254)+TX, mecarbam (502)+TX, mephosfolan (1261)+TX, mesulfen (alternative name) [CCN]+TX, methacrifos (1266)+TX, methamidophos (527)+TX, methidathion (529)+TX, methiocarb (530)+TX, methomyl (531)+TX, methyl bromide (537)+TX, metolcarb (550)+TX, mevinphos (556)+TX, mexacarbate (1290)+TX, milbemectin (557)+TX, milbemycin oxime (alternative name) [CCN]+TX, mipafox (1293)+TX, monocrotophos (561)+TX, morphothion (1300)+TX, moxidectin (alternative name) [CCN]+TX, naled (567)+TX, NC-184 (compound code)+TX, NC-512 (compound code)+TX, nifluridide (1309)+TX, nikkomycins (alternative name) [CCN]+TX, nitrilacarb (1313)+TX, nitrilacarb 1:1 zinc chloride complex (1313)+TX, NNI-0101 (compound code)+TX, NNI-0250 (compound code)+TX, omethoate (594)+TX, oxamyl (602)+TX, oxydeprofos (1324)+TX, oxydisulfoton (1325)+TX, pp′-DDT (219)+TX, parathion (615)+TX, permethrin (626)+TX, petroleum oils (alternative name) (628)+TX, phenkapton (1330)+TX, phenthoate (631)+TX, phorate (636)+TX, phosalone (637)+TX, phosfolan (1338)+TX, phosmet (638)+TX, phosphamidon (639)+TX, phoxim (642)+TX, pirimiphos-methyl (652)+TX, polychloroterpenes (traditional name) (1347)+TX, polynactins (alternative name) (653)+TX, proclonol (1350)+TX, profenofos (662)+TX, promacyl (1354)+TX, propargite (671)+TX, propetamphos (673)+TX, propoxur (678)+TX, prothidathion (1360)+TX, prothoate (1362)+TX, pyrethrin I (696)+TX, pyrethrin II (696)+TX, pyrethrins (696)+TX, pyridaben (699)+TX, pyridaphenthion (701)+TX, pyrimidifen (706)+TX, pyrimitate (1370)+TX, quinalphos (711)+TX, quintiofos (1381)+TX, R-1492 (development code) (1382)+TX, RA-17 (development code) (1383)+TX, rotenone (722)+TX, schradan (1389)+TX, sebufos (alternative name)+TX, selamectin (alternative name) [CCN]+TX, SI-0009 (compound code)+TX, sophamide (1402)+TX, spirodiclofen (738)+TX, spiromesifen (739)+TX, SSI-121 (development code) (1404)+TX, sulfiram (alternative name) [CCN]+TX, sulfluramid (750)+TX, sulfotep (753)+TX, sulfur (754)+TX, SZI-121 (development code) (757)+TX, tau-fluvalinate (398)+TX, tebufenpyrad (763)+TX, TEPP (1417)+TX, terbam (alternative name)+TX, tetrachlorvinphos (777)+TX, tetradifon (786)+TX, tetranactin (alternative name) (653)+TX, tetrasul (1425)+TX, thiafenox (alternative name)+TX, thiocarboxime (1431)+TX, thiofanox (800)+TX, thiometon (801)+TX, thioquinox (1436)+TX, thuringiensin (alternative name) [CCN]+TX, triamiphos (1441)+TX, triarathene (1443)+TX, triazophos (820)+TX, triazuron (alternative name)+TX, trichlorfon (824)+TX, trifenofos (1455)+TX, trinactin (alternative name) (653)+TX, vamidothion (847)+TX, vaniliprole [CCN] and YI-5302 (compound code)+TX, an algicide selected from the group of substances consisting of bethoxazin [CCN]+TX, copper dioctanoate (IUPAC name) (170)+TX, copper sulfate (172)+TX, cybutryne [CCN]+TX, dichlone (1052)+TX, dichlorophen (232)+TX, endothal (295)+TX, fentin (347)+TX, hydrated lime [CCN]+TX, nabam (566)+TX, quinoclamine (714)+TX, quinonamid (1379)+TX, simazine (730)+TX, triphenyltin acetate (IUPAC name) (347) and triphenyltin hydroxide (IUPAC name) (347)+TX, an anthelmintic selected from the group of substances consisting of abamectin (1)+TX, crufomate (1011)+TX, doramectin (alternative name) [CCN]+TX, emamectin (291)+TX, emamectin benzoate (291)+TX, eprinomectin (alternative name) [CCN]+TX, ivermectin (alternative name) [CCN]+TX, milbemycin oxime (alternative name) [CCN]+TX, moxidectin (alternative name) [CCN]+TX, piperazine [CCN]+TX, selamectin (alternative name) [CCN]+TX, spinosad (737) and thiophanate (1435)+TX, an avicide selected from the group of substances consisting of chloralose (127)+TX, endrin (1122)+TX, fenthion (346)+TX, pyridin-4-amine (IUPAC name) (23) and strychnine (745)+TX, a bactericide selected from the group of substances consisting of 1-hydroxy-1H-pyridine-2-thione (IUPAC name) (1222)+TX, 4-(quinoxalin-2-ylamino)benzenesulfonamide (IUPAC name) (748)+TX, 8-hydroxyquinoline sulfate (446)+TX, bronopol (97)+TX, copper dioctanoate (IUPAC name) (170)+TX, copper hydroxide (IUPAC name) (169)+TX, cresol [CCN]+TX, dichlorophen (232)+TX, dipyrithione (1105)+TX, dodicin (1112)+TX, fenaminosulf (1144)+TX, formaldehyde (404)+TX, hydrargaphen (alternative name) [CCN]+TX, kasugamycin (483)+TX, kasugamycin hydrochloride hydrate (483)+TX, nickel bis(dimethyldithiocarbamate) (IUPAC name) (1308)+TX, nitrapyrin (580)+TX, octhilinone (590)+TX, oxolinic acid (606)+TX, oxytetracycline (611)+TX, potassium hydroxyquinoline sulfate (446)+TX, probenazole (658)+TX, streptomycin (744)+TX, streptomycin sesquisulfate (744)+TX, tecloftalam (766)+TX, and thiomersal (alternative name) [CCN]+TX, a biological agent selected from the group of substances consisting of Adoxophyes orana GV (alternative name) (12)+TX, Agrobacterium radiobacter (alternative name) (13)+TX, Amblyseius spp. (alternative name) (19)+TX, Anagrapha falcifera NPV (alternative name) (28)+TX, Anagrus atomus (alternative name) (29)+TX, Aphelinus abdominalis (alternative name) (33)+TX, Aphidius colemani (alternative name) (34)+TX, Aphidoletes aphidimyza (alternative name) (35)+TX, Autographa californica NPV (alternative name) (38)+TX, Bacillus firmus (alternative name) (48)+TX, Bacillus sphaericus Neide (scientific name) (49)+TX, Bacillus thuringiensis Berliner (scientific name) (51)+TX, Bacillus thuringiensis subsp. aizawai (scientific name) (51)+TX, Bacillus thuringiensis subsp. israelensis (scientific name) (51)+TX, Bacillus thuringiensis subsp. japonensis (scientific name) (51)+TX, Bacillus thuringiensis subsp. kurstaki (scientific name) (51)+TX, Bacillus thurin-giensis subsp. tenebrionis (scientific name) (51)+TX, Beauveria bassiana (alternative name) (53)+TX, Beauveria brongniartii (alternative name) (54)+TX, Chrysoperla carnea (alternative name) (151)+TX, Cryptolaemus montrouzieri (alternative name) (178)+TX, Cydia pomonella GV (alternative name) (191)+TX, Dacnusa sibirica (alternative name) (212)+TX, Diglyphus isaea (alternative name) (254)+TX, Encarsia formosa (scientific name) (293)+TX, Eretmocerus eremicus (alternative name) (300)+TX, Helicoverpa zea NPV (alternative name) (431)+TX, Heterorhabditis bacteriophora and H. megidis (alternative name) (433)+TX, Hippodamia convergens (alternative name) (442)+TX, Leptomastix dactylopii (alternative name) (488)+TX, Macrolophus caliginosus (alternative name) (491)+TX, Mamestra brassicae NPV (alternative name) (494)+TX, Metaphycus helvolus (alternative name) (522)+TX, Metarhizium anisopliae var. acridum (scientific name) (523)+TX, Metarhizium anisopliae var. anisopliae (scientific name) (523)+TX, Neodiprion sertifer NPV and N. lecontei NPV (alternative name) (575)+TX, Orius spp. (alternative name) (596)+TX, Paecilomyces fumosoroseus (alternative name) (613)+TX, Phytoseiulus persimilis (alternative name) (644)+TX, Spodoptera exigua multicapsid nuclear polyhedrosis virus (scientific name) (741)+TX, Steinernema bibionis (alternative name) (742)+TX, Steinernema carpocapsae (alternative name) (742)+TX, Steinernema feltiae (alternative name) (742)+TX, Steinernema glaseri (alternative name) (742)+TX, Steinernema riobrave (alternative name) (742)+TX, Steinernema riobravis (alternative name) (742)+TX, Steinernema scapterisci (alternative name) (742)+TX, Steinernema spp. (alternative name) (742)+TX, Trichogramma spp. (alternative name) (826)+TX, Typhlodromus occidentalis (alternative name) (844) and Verticillium lecanii (alternative name) (848)+TX, a soil sterilant selected from the group of substances consisting of iodomethane (IUPAC name) (542) and methyl bromide (537)+TX, a chemosterilant selected from the group of substances consisting of apholate [CCN]+TX, bisazir (alternative name) [CCN]+TX, busulfan (alternative name) [CCN]+TX, diflubenzuron (250)+TX, dimatif (alternative name) [CCN]+TX, hemel [CCN]+TX, hempa [CCN]+TX, metepa [CCN]+TX, methiotepa [CCN]+TX, methyl apholate [CCN]+TX, morzid [CCN]+TX, penfluron (alternative name) [CCN]+TX, tepa [CCN]+TX, thiohempa (alternative name) [CCN]+TX, thiotepa (alternative name) [CCN]+TX, tretamine (alternative name) [CCN] and uredepa (alternative name) [CCN]+TX, an insect pheromone selected from the group of substances consisting of (E)-dec-5-en-1-yl acetate with (E)-dec-5-en-1-ol (IUPAC name) (222)+TX, (E)-tridec-4-en-1-yl acetate (IUPAC name) (829)+TX, (E)-6-methylhept-2-en-4-ol (IUPAC name) (541)+TX, (E,Z)-tetradeca-4,10-dien-1-yl acetate (IUPAC name) (779)+TX, (Z)-dodec-7-en-1-yl acetate (IUPAC name) (285)+TX, (Z)-hexadec-11-enal (IUPAC name) (436)+TX, (Z)-hexadec-11-en-1-yl acetate (IUPAC name) (437)+TX, (Z)-hexadec-13-en-11-yn-1-yl acetate (IUPAC name) (438)+TX, (Z)-icos-13-en-10-one (IUPAC name) (448)+TX, (Z)-tetradec-7-en-1-al (IUPAC name) (782)+TX, (Z)-tetradec-9-en-1-ol (IUPAC name) (783)+TX, (Z)-tetradec-9-en-1-yl acetate (IUPAC name) (784)+TX, (7E,9Z)-dodeca-7,9-dien-1-yl acetate (IUPAC name) (283)+TX, (9Z,11E)-tetradeca-9,11-dien-1-yl acetate (IUPAC name) (780)+TX, (9Z,12E)-tetradeca-9,12-dien-1-yl acetate (IUPAC name) (781)+TX, 14-methyloctadec-1-ene (IUPAC name) (545)+TX, 4-methylnonan-5-ol with 4-methylnonan-5-one (IUPAC name) (544)+TX, alpha-multistriatin (alternative name) [CCN]+TX, brevicomin (alternative name) [CCN]+TX, codlelure (alternative name) [CCN]+TX, codlemone (alternative name) (167)+TX, cuelure (alternative name) (179)+TX, disparlure (277)+TX, dodec-8-en-1-yl acetate (IUPAC name) (286)+TX, dodec-9-en-1-yl acetate (IUPAC name) (287)+TX, dodeca-8+TX, 10-dien-1-yl acetate (IUPAC name) (284)+TX, dominicalure (alternative name) [CCN]+TX, ethyl 4-methyloctanoate (IUPAC name) (317)+TX, eugenol (alternative name) [CCN]+TX, frontalin (alternative name) [CCN]+TX, gossyplure (alternative name) (420)+TX, grandlure (421)+TX, grandlure I (alternative name) (421)+TX, grandlure II (alternative name) (421)+TX, grandlure III (alternative name) (421)+TX, grandlure IV (alternative name) (421)+TX, hexalure [CCN]+TX, ipsdienol (alternative name) [CCN]+TX, ipsenol (alternative name) [CCN]+TX, japonilure (alternative name) (481)+TX, lineatin (alternative name) [CCN]+TX, litlure (alternative name) [CCN]+TX, looplure (alternative name) [CCN]+TX, medlure [CCN]+TX, megatomoic acid (alternative name) [CCN]+TX, methyl eugenol (alternative name) (540)+TX, muscalure (563)+TX, octadeca-2,13-dien-1-yl acetate (IUPAC name) (588)+TX, octadeca-3,13-dien-1-yl acetate (IUPAC name) (589)+TX, orfralure (alternative name) [CCN]+TX, oryctalure (alternative name) (317)+TX, ostramone (alternative name) [CCN]+TX, siglure [CCN]+TX, sordid in (alternative name) (736)+TX, sulcatol (alternative name) [CCN]+TX, tetradec-11-en-1-yl acetate (IUPAC name) (785)+TX, trimedlure (839)+TX, trimedlure A (alternative name) (839)+TX, trimedlure B.sub.1 (alternative name) (839)+TX, trimedlure B.sub.2 (alternative name) (839)+TX, trimedlure C (alternative name) (839) and trunc-call (alternative name) [CCN]+TX, an insect repellent selected from the group of substances consisting of 2-(octylthio)ethanol (IUPAC name) (591)+TX, butopyronoxyl (933)+TX, butoxy(polypropylene glycol) (936)+TX, dibutyl adipate (IUPAC name) (1046)+TX, dibutyl phthalate (1047)+TX, dibutyl succinate (IUPAC name) (1048)+TX, diethyltoluamide [CCN]+TX, dimethyl carbate [CCN]+TX, dimethyl phthalate [CCN]+TX, ethyl hexanediol (1137)+TX, hexamide [CCN]+TX, methoquin-butyl (1276)+TX, methylneodecanamide [CCN]+TX, oxamate [CCN] and picaridin [CCN]+TX, an insecticide selected from the group of substances consisting of 1-dichloro-1-nitroethane (IUPAC/Chemical Abstracts name) (1058)+TX, 1,1-dichloro-2,2-bis(4-ethylphenyl)ethane (IUPAC name) (1056), +TX, 1,2-dichloropropane (IUPAC/Chemical Abstracts name) (1062)+TX, 1,2-dichloropropane with 1,3-dichloropropene (IUPAC name) (1063)+TX, 1-bromo-2-chloroethane (IUPAC/Chemical Abstracts name) (916)+TX, 2,2,2-trichloro-1-(3,4-dichlorophenyl)ethyl acetate (IUPAC name) (1451)+TX, 2,2-dichlorovinyl 2-ethylsulfinylethyl methyl phosphate (IUPAC name) (1066)+TX, 2-(1,3-dithiolan-2-yl)phenyl dimethylcarbamate (IUPAC/Chemical Abstracts name) (1109)+TX, 2-(2-butoxyethoxy)ethyl thiocyanate (IUPAC/Chemical Abstracts name) (935)+TX, 2-(4,5-dimethyl-1,3-dioxolan-2-yl)phenyl methylcarbamate (IUPAC/Chemical Abstracts name) (1084)+TX, 2-(4-chloro-3,5-xylyloxy)ethanol (IUPAC name) (986)+TX, 2-chlorovinyl diethyl phosphate (IUPAC name) (984)+TX, 2-imidazolidone (IUPAC name) (1225)+TX, 2-isovalerylindan-1,3-dione (IUPAC name) (1246)+TX, 2-methyl(prop-2-ynyl)aminophenyl methylcarbamate (IUPAC name) (1284)+TX, 2-thiocyanatoethyl laurate (IUPAC name) (1433)+TX, 3-bromo-1-chloroprop-1-ene (IUPAC name) (917)+TX, 3-methyl-1-phenylpyrazol-5-yl dimethylcarbamate (IUPAC name) (1283)+TX, 4-methyl(prop-2-ynyl)amino-3,5-xylyl methylcarbamate (IUPAC name) (1285)+TX, 5,5-dimethyl-3-oxocyclohex-1-enyl dimethylcarbamate (IUPAC name) (1085)+TX, abamectin (1)+TX, acephate (2)+TX, acetamiprid (4)+TX, acethion (alternative name) [CCN]+TX, acetoprole [CCN]+TX, acrinathrin (9)+TX, acrylonitrile (IUPAC name) (861)+TX, alanycarb (15)+TX, aldicarb (16)+TX, aldoxycarb (863)+TX, aldrin (864)+TX, allethrin (17)+TX, allosamidin (alternative name) [CCN]+TX, allyxycarb (866)+TX, alpha-cypermethrin (202)+TX, alpha-ecdysone (alternative name) [CCN]+TX, aluminium phosphide (640)+TX, amidithion (870)+TX, amidothioate (872)+TX, aminocarb (873)+TX, amiton (875)+TX, amiton hydrogen oxalate (875)+TX, amitraz (24)+TX, anabasine (877)+TX, athidathion (883)+TX, AVI 382 (compound code)+TX, AZ 60541 (compound code)+TX, azadirachtin (alternative name) (41)+TX, azamethiphos (42)+TX, azinphos-ethyl (44)+TX, azinphos-methyl (45)+TX, azothoate (889)+TX, Bacillus thuringiensis delta endotoxins (alternative name) (52)+TX, barium hexafluorosilicate (alternative name) [CCN]+TX, barium polysulfide (IUPAC/Chemical Abstracts name) (892)+TX, barthrin [CCN]+TX, Bayer 22/190 (development code) (893)+TX, Bayer 22408 (development code) (894)+TX, bendiocarb (58)+TX, benfuracarb (60)+TX, bensultap (66)+TX, beta-cyfluthrin (194)+TX, beta-cypermethrin (203)+TX, bifenthrin (76)+TX, bioallethrin (78)+TX, bioallethrin S-cyclopentenyl isomer (alternative name) (79)+TX, bioethanomethrin [CCN]+TX, biopermethrin (908)+TX, bioresmethrin (80)+TX, bis(2-chloroethyl) ether (IUPAC name) (909)+TX, bistrifluron (83)+TX, borax (86)+TX, brofenvalerate (alternative name)+TX, bromfenvinfos (914)+TX, bromocyclen (918)+TX, bromo-DDT (alternative name) [CCN]+TX, bromophos (920)+TX, bromophos-ethyl (921)+TX, bufencarb (924)+TX, buprofezin (99)+TX, butacarb (926)+TX, butathiofos (927)+TX, butocarboxim (103)+TX, butonate (932)+TX, butoxycarboxim (104)+TX, butylpyridaben (alternative name)+TX, cadusafos (109)+TX, calcium arsenate [CCN]+TX, calcium cyanide (444)+TX, calcium polysulfide (IUPAC name) (111)+TX, camphechlor (941)+TX, carbanolate (943)+TX, carbaryl (115)+TX, carbofuran (118)+TX, carbon disulfide (IUPAC/Chemical Abstracts name) (945)+TX, carbon tetrachloride (IUPAC name) (946)+TX, carbophenothion (947)+TX, carbosulfan (119)+TX, cartap (123)+TX, cartap hydrochloride (123)+TX, cevadine (alternative name) (725)+TX, chlorbicyclen (960)+TX, chlordane (128)+TX, chlordecone (963)+TX, chlordimeform (964)+TX, chlordimeform hydrochloride (964)+TX, chlorethoxyfos (129)+TX, chlorfenapyr (130)+TX, chlorfenvinphos (131)+TX, chlorfluazuron (132)+TX, chlormephos (136)+TX, chloroform [CCN]+TX, chloropicrin (141)+TX, chlorphoxim (989)+TX, chlorprazophos (990)+TX, chlorpyrifos (145)+TX, chlorpyrifos-methyl (146)+TX, chlorthiophos (994)+TX, chromafenozide (150)+TX, cinerin I (696)+TX, cinerin II (696)+TX, cinerins (696)+TX, cis-resmethrin (alternative name)+TX, cismethrin (80)+TX, clocythrin (alternative name)+TX, cloethocarb (999)+TX, closantel (alternative name) [CCN]+TX, clothianidin (165)+TX, copper acetoarsenite [CCN]+TX, copper arsenate [CCN]+TX, copper oleate [CCN]+TX, coumaphos (174)+TX, coumithoate (1006)+TX, crotamiton (alternative name) [CCN]+TX, crotoxyphos (1010)+TX, crufomate (1011)+TX, cryolite (alternative name) (177)+TX, CS 708 (development code) (1012)+TX, cyanofenphos (1019)+TX, cyanophos (184)+TX, cyanthoate (1020)+TX, cyclethrin [CCN]+TX, cycloprothrin (188)+TX, cyfluthrin (193)+TX, cyhalothrin (196)+TX, cypermethrin (201)+TX, cyphenothrin (206)+TX, cyromazine (209)+TX, cythioate (alternative name) [CCN]+TX, d-limonene (alternative name) [CCN]+TX, d-tetramethrin (alternative name) (788)+TX, DAEP (1031)+TX, dazomet (216)+TX, DDT (219)+TX, decarbofuran (1034)+TX, deltamethrin (223)+TX, demephion (1037)+TX, demephion-O (1037)+TX, demephion-S (1037)+TX, demeton (1038)+TX, demeton-methyl (224)+TX, demeton-O (1038)+TX, demeton-O-methyl (224)+TX, demeton-S (1038)+TX, demeton-S-methyl (224)+TX, demeton-S-methylsulphon (1039)+TX, diafenthiuron (226)+TX, dialifos (1042)+TX, diamidafos (1044)+TX, diazinon (227)+TX, dicapthon (1050)+TX, dichlofenthion (1051)+TX, dichlorvos (236)+TX, dicliphos (alternative name)+TX, dicresyl (alternative name) [CCN]+TX, dicrotophos (243)+TX, dicyclanil (244)+TX, dieldrin (1070)+TX, diethyl 5-methylpyrazol-3-yl phosphate (IUPAC name) (1076)+TX, diflubenzuron (250)+TX, dilor (alternative name) [CCN]+TX, dimefluthrin [CCN]+TX, dimefox (1081)+TX, dimetan (1085)+TX, dimethoate (262)+TX, dimethrin (1083)+TX, dimethylvinphos (265)+TX, dimetilan (1086)+TX, dinex (1089)+TX, dinex-diclexine (1089)+TX, dinoprop (1093)+TX, dinosam (1094)+TX, dinoseb (1095)+TX, dinotefuran (271)+TX, diofenolan (1099)+TX, dioxabenzofos (1100)+TX, dioxacarb (1101)+TX, dioxathion (1102)+TX, disulfoton (278)+TX, dithicrofos (1108)+TX, DNOC (282)+TX, doramectin (alternative name) [CCN]+TX, DSP (1115)+TX, ecdysterone (alternative name) [CCN]+TX, EI 1642 (development code) (1118)+TX, emamectin (291)+TX, emamectin benzoate (291)+TX, EMPC (1120)+TX, empenthrin (292)+TX, endosulfan (294)+TX, endothion (1121)+TX, endrin (1122)+TX, EPBP (1123)+TX, EPN (297)+TX, epofenonane (1124)+TX, eprinomectin (alternative name) [CCN]+TX, esfenvalerate (302)+TX, etaphos (alternative name) [CCN]+TX, ethiofencarb (308)+TX, ethion (309)+TX, ethiprole (310)+TX, ethoate-methyl (1134)+TX, ethoprophos (312)+TX, ethyl formate (IUPAC name) [CCN]+TX, ethyl-DDD (alternative name) (1056)+TX, ethylene dibromide (316)+TX, ethylene dichloride (chemical name) (1136)+TX, ethylene oxide [CCN]+TX, etofenprox (319)+TX, etrimfos (1142)+TX, EXD (1143)+TX, famphur (323)+TX, fenamiphos (326)+TX, fenazaflor (1147)+TX, fenchlorphos (1148)+TX, fenethacarb (1149)+TX, fenfluthrin (1150)+TX, fenitrothion (335)+TX, fenobucarb (336)+TX, fenoxacrim (1153)+TX, fenoxycarb (340)+TX, fenpirithrin (1155)+TX, fenpropathrin (342)+TX, fenpyrad (alternative name)+TX, fensulfothion (1158)+TX, fenthion (346)+TX, fenthion-ethyl [CCN]+TX, fenvalerate (349)+TX, fipronil (354)+TX, flonicamid (358)+TX, flubendiamide (CAS. Reg. No.: 272451-65-7)+TX, flucofuron (1168)+TX, flucycloxuron (366)+TX, flucythrinate (367)+TX, fluenetil (1169)+TX, flufenerim [CCN]+TX, flufenoxuron (370)+TX, flufenprox (1171)+TX, flumethrin (372)+TX, fluvalinate (1184)+TX, FMC 1137 (development code) (1185)+TX, fonofos (1191)+TX, formetanate (405)+TX, formetanate hydrochloride (405)+TX, formothion (1192)+TX, formparanate (1193)+TX, fosmethilan (1194)+TX, fospirate (1195)+TX, fosthiazate (408)+TX, fosthietan (1196)+TX, furathiocarb (412)+TX, furethrin (1200)+TX, gamma-cyhalothrin (197)+TX, gamma-HCH (430)+TX, guazatine (422)+TX, guazatine acetates (422)+TX, GY-81 (development code) (423)+TX, halfenprox (424)+TX, halofenozide (425)+TX, HCH (430)+TX, HEOD (1070)+TX, heptachlor (1211)+TX, heptenophos (432)+TX, heterophos [CCN]+TX, hexaflumuron (439)+TX, HHDN (864)+TX, hydramethylnon (443)+TX, hydrogen cyanide (444)+TX, hydroprene (445)+TX, hyquincarb (1223)+TX, imidacloprid (458)+TX, imiprothrin (460)+TX, indoxacarb (465)+TX, iodomethane (IUPAC name) (542)+TX, IPSP (1229)+TX, isazofos (1231)+TX, isobenzan (1232)+TX, isocarbophos (alternative name) (473)+TX, isodrin (1235)+TX, isofenphos (1236)+TX, isolane (1237)+TX, isoprocarb (472)+TX, isopropyl O-(methoxy-aminothiophosphoryl)salicylate (IUPAC name) (473)+TX, isoprothiolane (474)+TX, isothioate (1244)+TX, isoxathion (480)+TX, ivermectin (alternative name) [CCN]+TX, jasmolin I (696)+TX, jasmolin II (696)+TX, jodfenphos (1248)+TX, juvenile hormone I (alternative name) [CCN]+TX, juvenile hormone II (alternative name) [CCN]+TX, juvenile hormone III (alternative name) [CCN]+TX, kelevan (1249)+TX, kinoprene (484)+TX, lambda-cyhalothrin (198)+TX, lead arsenate [CCN]+TX, lepimectin (CCN)+TX, leptophos (1250)+TX, lindane (430)+TX, lirimfos (1251)+TX, lufenuron (490)+TX, lythidathion (1253)+TX, m-cumenyl methylcarbamate (IUPAC name) (1014)+TX, magnesium phosphide (IUPAC name) (640)+TX, malathion (492)+TX, malonoben (1254)+TX, mazidox (1255)+TX, mecarbam (502)+TX, mecarphon (1258)+TX, menazon (1260)+TX, mephosfolan (1261)+TX, mercurous chloride (513)+TX, mesulfenfos (1263)+TX, metaflumizone (CCN)+TX, metam (519)+TX, metam-potassium (alternative name) (519)+TX, metam-sodium (519)+TX, methacrifos (1266)+TX, methamidophos (527)+TX, methanesulfonyl fluoride (IUPAC/Chemical Abstracts name) (1268)+TX, methidathion (529)+TX, methiocarb (530)+TX, methocrotophos (1273)+TX, methomyl (531)+TX, methoprene (532)+TX, methoquin-butyl (1276)+TX, methothrin (alternative name) (533)+TX, methoxychlor (534)+TX, methoxyfenozide (535)+TX, methyl bromide (537)+TX, methyl isothiocyanate (543)+TX, methylchloroform (alternative name) [CCN]+TX, methylene chloride [CCN]+TX, metofluthrin [CCN]+TX, metolcarb (550)+TX, metoxadiazone (1288)+TX, mevinphos (556)+TX, mexacarbate (1290)+TX, milbemectin (557)+TX, milbemycin oxime (alternative name) [CCN]+TX, mipafox (1293)+TX, mirex (1294)+TX, monocrotophos (561)+TX, morphothion (1300)+TX, moxidectin (alternative name) [CCN]+TX, naftalofos (alternative name) [CCN]+TX, naled (567)+TX, naphthalene (IUPAC/Chemical Abstracts name) (1303)+TX, NC-170 (development code) (1306)+TX, NC-184 (compound code)+TX, nicotine (578)+TX, nicotine sulfate (578)+TX, nifluridide (1309)+TX, nitenpyram (579)+TX, nithiazine (1311)+TX, nitrilacarb (1313)+TX, nitrilacarb 1:1 zinc chloride complex (1313)+TX, NNI-0101 (compound code)+TX, NNI-0250 (compound code)+TX, nornicotine (traditional name) (1319)+TX, novaluron (585)+TX, noviflumuron (586)+TX, O-5-dichloro-4-iodophenyl O-ethyl ethylphosphonothioate (IUPAC name) (1057)+TX, O,O-diethyl O-4-methyl-2-oxo-2H-chromen-7-yl phosphorothioate (IUPAC name) (1074)+TX, O,O-diethyl O-6-methyl-2-propylpyrimidin-4-yl phosphorothioate (IUPAC name) (1075)+TX, O,O,O′,O′-tetrapropyl dithiopyrophosphate (IUPAC name) (1424)+TX, oleic acid (IUPAC name) (593)+TX, omethoate (594)+TX, oxamyl (602)+TX, oxydemeton-methyl (609)+TX, oxydeprofos (1324)+TX, oxydisulfoton (1325)+TX, pp′-DDT (219)+TX, para-dichlorobenzene [CCN]+TX, parathion (615)+TX, parathion-methyl (616)+TX, penfluron (alternative name) [CCN]+TX, pentachlorophenol (623)+TX, pentachlorophenyl laurate (IUPAC name) (623)+TX, permethrin (626)+TX, petroleum oils (alternative name) (628)+TX, PH 60-38 (development code) (1328)+TX, phenkapton (1330)+TX, phenothrin (630)+TX, phenthoate (631)+TX, phorate (636)+TX, phosalone (637)+TX, phosfolan (1338)+TX, phosmet (638)+TX, phosnichlor (1339)+TX, phosphamidon (639)+TX, phosphine (IUPAC name) (640)+TX, phoxim (642)+TX, phoxim-methyl (1340)+TX, pirimetaphos (1344)+TX, pirimicarb (651)+TX, pirimiphos-ethyl (1345)+TX, pirimiphos-methyl (652)+TX, polychlorodicyclopentadiene isomers (IUPAC name) (1346)+TX, polychloroterpenes (traditional name) (1347)+TX, potassium arsenite [CCN]+TX, potassium thiocyanate [CCN]+TX, prallethrin (655)+TX, precocene I (alternative name) [CCN]+TX, precocene II (alternative name) [CCN]+TX, precocene III (alternative name) [CCN]+TX, primidophos (1349)+TX, profenofos (662)+TX, profluthrin [CCN]+TX, promacyl (1354)+TX, promecarb (1355)+TX, propaphos (1356)+TX, propetamphos (673)+TX, propoxur (678)+TX, prothidathion (1360)+TX, prothiofos (686)+TX, prothoate (1362)+TX, protrifenbute [CCN]+TX, pymetrozine (688)+TX, pyraclofos (689)+TX, pyrazophos (693)+TX, pyresmethrin (1367)+TX, pyrethrin I (696)+TX, pyrethrin II (696)+TX, pyrethrins (696)+TX, pyridaben (699)+TX, pyridalyl (700)+TX, pyridaphenthion (701)+TX, pyrimidifen (706)+TX, pyrimitate (1370)+TX, pyriproxyfen (708)+TX, quassia (alternative name) [CCN]+TX, quinalphos (711)+TX, quinalphos-methyl (1376)+TX, quinothion (1380)+TX, quintiofos (1381)+TX, R-1492 (development code) (1382)+TX, rafoxanide (alternative name) [CCN]+TX, resmethrin (719)+TX, rotenone (722)+TX, RU 15525 (development code) (723)+TX, RU 25475 (development code) (1386)+TX, ryania (alternative name) (1387)+TX, ryanodine (traditional name) (1387)+TX, sabadilla (alternative name) (725)+TX, schradan (1389)+TX, sebufos (alternative name)+TX, selamectin (alternative name) [CCN]+TX, SI-0009 (compound code)+TX, SI-0205 (compound code)+TX, SI-0404 (compound code)+TX, SI-0405 (compound code)+TX, silafluofen (728)+TX, SN 72129 (development code) (1397)+TX, sodium arsenite [CCN]+TX, sodium cyanide (444)+TX, sodium fluoride (IUPAC/Chemical Abstracts name) (1399)+TX, sodium hexafluorosilicate (1400)+TX, sodium pentachlorophenoxide (623)+TX, sodium selenate (IUPAC name) (1401)+TX, sodium thiocyanate [CCN]+TX, sophamide (1402)+TX, spinosad (737)+TX, spiromesifen (739)+TX, spirotetrmat (CCN)+TX, sulcofuron (746)+TX, sulcofuron-sodium (746)+TX, sulfluramid (750)+TX, sulfotep (753)+TX, sulfuryl fluoride (756)+TX, sulprofos (1408)+TX, tar oils (alternative name) (758)+TX, tau-fluvalinate (398)+TX, tazimcarb (1412)+TX, TDE (1414)+TX, tebufenozide (762)+TX, tebufenpyrad (763)+TX, tebupirimfos (764)+TX, teflubenzuron (768)+TX, tefluthrin (769)+TX, temephos (770)+TX, TEPP (1417)+TX, terallethrin (1418)+TX, terbam (alternative name)+TX, terbufos (773)+TX, tetrachloroethane [CCN]+TX, tetrachlorvinphos (777)+TX, tetramethrin (787)+TX, theta-cypermethrin (204)+TX, thiacloprid (791)+TX, thiafenox (alternative name)+TX, thiamethoxam (792)+TX, thicrofos (1428)+TX, thiocarboxime (1431)+TX, thiocyclam (798)+TX, thiocyclam hydrogen oxalate (798)+TX, thiodicarb (799)+TX, thiofanox (800)+TX, thiometon (801)+TX, thionazin (1434)+TX, thiosultap (803)+TX, thiosultap-sodium (803)+TX, thuringiensin (alternative name) [CCN]+TX, tolfenpyrad (809)+TX, tralomethrin (812)+TX, transfluthrin (813)+TX, transpermethrin (1440)+TX, triamiphos (1441)+TX, triazamate (818)+TX, triazophos (820)+TX, triazuron (alternative name)+TX, trichlorfon (824)+TX, trichlormetaphos-3 (alternative name) [CCN]+TX, trichloronat (1452)+TX, trifenofos (1455)+TX, triflumuron (835)+TX, trimethacarb (840)+TX, triprene (1459)+TX, vamidothion (847)+TX, vaniliprole [CCN]+TX, veratridine (alternative name) (725)+TX, veratrine (alternative name) (725)+TX, XMC (853)+TX, xylylcarb (854)+TX, YI-5302 (compound code)+TX, zeta-cypermethrin (205)+TX, zetamethrin (alternative name)+TX, zinc phosphide (640)+TX, zolaprofos (1469) and ZXI 8901 (development code) (858)+TX, cyantraniliprole [736994-63-19+TX, chlorantraniliprole [500008-45-7]+TX, cyenopyrafen [560121-52-0]+TX, cyflumetofen [400882-07-7]+TX, pyrifluquinazon [337458-27-2]+TX, spinetoram [187166-40-1+187166-15-0]+TX, spirotetramat [203313-25-1]+TX, sulfoxaflor [946578-00-3]+TX, flufiprole [704886-18-0]+TX, meperfluthrin [915288-13-0]+TX, tetramethylfluthrin [84937-88-2]+TX, triflumezopyrim (disclosed in WO 2012/092115)+TX, a molluscicide selected from the group of substances consisting of bis(tributyltin) oxide (IUPAC name) (913)+TX, bromoacetamide [CCN]+TX, calcium arsenate [CCN]+TX, cloethocarb (999)+TX, copper acetoarsenite [CCN]+TX, copper sulfate (172)+TX, fentin (347)+TX, ferric phosphate (IUPAC name) (352)+TX, metaldehyde (518)+TX, methiocarb (530)+TX, niclosamide (576)+TX, niclosamide-olamine (576)+TX, pentachlorophenol (623)+TX, sodium pentachlorophenoxide (623)+TX, tazimcarb (1412)+TX, thiodicarb (799)+TX, tributyltin oxide (913)+TX, trifenmorph (1454)+TX, trimethacarb (840)+TX, triphenyltin acetate (IUPAC name) (347) and triphenyltin hydroxide (IUPAC name) (347)+TX, pyriprole [394730-71-3]+TX, a nematicide selected from the group of substances consisting of AKD-3088 (compound code)+TX, 1,2-dibromo-3-chloropropane (IUPAC/Chemical Abstracts name) (1045)+TX, 1,2-dichloropropane (IUPAC/Chemical Abstracts name) (1062)+TX, 1,2-dichloropropane with 1,3-dichloropropene (IUPAC name) (1063)+TX, 1,3-dichloropropene (233)+TX, 3,4-dichlorotetrahydrothiophene 1,1-dioxide (IUPAC/Chemical Abstracts name) (1065)+TX, 3-(4-chlorophenyl)-5-methylrhodamine (IUPAC name) (980)+TX, 5-methyl-6-thioxo-1,3,5-thiadiazinan-3-ylacetic acid (IUPAC name) (1286)+TX, 6-isopentenylaminopurine (alternative name) (210)+TX, abamectin (1)+TX, acetoprole [CCN]+TX, alanycarb (15)+TX, aldicarb (16)+TX, aldoxycarb (863)+TX, AZ 60541 (compound code)+TX, benclothiaz [CCN]+TX, benomyl (62)+TX, butylpyridaben (alternative name)+TX, cadusafos (109)+TX, carbofuran (118)+TX, carbon disulfide (945)+TX, carbosulfan (119)+TX, chloropicrin (141)+TX, chlorpyrifos (145)+TX, cloethocarb (999)+TX, cytokinins (alternative name) (210)+TX, dazomet (216)+TX, DBCP (1045)+TX, DCIP (218)+TX, diamidafos (1044)+TX, dichlofenthion (1051)+TX, dicliphos (alternative name)+TX, dimethoate (262)+TX, doramectin (alternative name) [CCN]+TX, emamectin (291)+TX, emamectin benzoate (291)+TX, eprinomectin (alternative name) [CCN]+TX, ethoprophos (312)+TX, ethylene dibromide (316)+TX, fenamiphos (326)+TX, fenpyrad (alternative name)+TX, fensulfothion (1158)+TX, fosthiazate (408)+TX, fosthietan (1196)+TX, furfural (alternative name) [CCN]+TX, GY-81 (development code) (423)+TX, heterophos [CCN]+TX, iodomethane (IUPAC name) (542)+TX, isamidofos (1230)+TX, isazofos (1231)+TX, ivermectin (alternative name) [CCN]+TX, kinetin (alternative name) (210)+TX, mecarphon (1258)+TX, metam (519)+TX, metam-potassium (alternative name) (519)+TX, metam-sodium (519)+TX, methyl bromide (537)+TX, methyl isothiocyanate (543)+TX, milbemycin oxime (alternative name) [CCN]+TX, moxidectin (alternative name) [CCN]+TX, Myrothecium verrucaria composition (alternative name) (565)+TX, NC-184 (compound code)+TX, oxamyl (602)+TX, phorate (636)+TX, phosphamidon (639)+TX, phosphocarb [CCN]+TX, sebufos (alternative name)+TX, selamectin (alternative name) [CCN]+TX, spinosad (737)+TX, terbam (alternative name)+TX, terbufos (773)+TX, tetrachlorothiophene (IUPAC/Chemical Abstracts name) (1422)+TX, thiafenox (alternative name)+TX, thionazin (1434)+TX, triazophos (820)+TX, triazuron (alternative name)+TX, xylenols [CCN]+TX, YI-5302 (compound code) and zeatin (alternative name) (210)+TX, fluensulfone [318290-98-1]+TX, a nitrification inhibitor selected from the group of substances consisting of potassium ethylxanthate [CCN] and nitrapyrin (580)+TX, a plant activator selected from the group of substances consisting of acibenzolar (6)+TX, acibenzolar-S-methyl (6)+TX, probenazole (658) and Reynoutria sachalinensis extract (alternative name) (720)+TX, a rodenticide selected from the group of substances consisting of 2-isovalerylindan-1,3-dione (IUPAC name) (1246)+TX, 4-(quinoxalin-2-ylamino)benzenesulfonamide (IUPAC name) (748)+TX, alpha-chlorohydrin [CCN]+TX, aluminium phosphide (640)+TX, antu (880)+TX, arsenous oxide (882)+TX, barium carbonate (891)+TX, bisthiosemi (912)+TX, brodifacoum (89)+TX, bromadiolone (91)+TX, bromethalin (92)+TX, calcium cyanide (444)+TX, chloralose (127)+TX, chlorophacinone (140)+TX, cholecalciferol (alternative name) (850)+TX, coumachlor (1004)+TX, coumafuryl (1005)+TX, coumatetralyl (175)+TX, crimidine (1009)+TX, difenacoum (246)+TX, difethialone (249)+TX, diphacinone (273)+TX, ergocalciferol (301)+TX, flocoumafen (357)+TX, fluoroacetamide (379)+TX, flupropadine (1183)+TX, flupropadine hydrochloride (1183)+TX, gamma-HCH (430)+TX, HCH (430)+TX, hydrogen cyanide (444)+TX, iodomethane (IUPAC name) (542)+TX, lindane (430)+TX, magnesium phosphide (IUPAC name) (640)+TX, methyl bromide (537)+TX, norbormide (1318)+TX, phosacetim (1336)+TX, phosphine (IUPAC name) (640)+TX, phosphorus [CCN]+TX, pindone (1341)+TX, potassium arsenite [CCN]+TX, pyrinuron (1371)+TX, scilliroside (1390)+TX, sodium arsenite [CCN]+TX, sodium cyanide (444)+TX, sodium fluoroacetate (735)+TX, strychnine (745)+TX, thallium sulfate [CCN]+TX, warfarin (851) and zinc phosphide (640)+TX, a synergist selected from the group of substances consisting of 2-(2-butoxyethoxy)ethyl piperonylate (IUPAC name) (934)+TX, 5-(1,3-benzodioxol-5-yl)-3-hexylcyclohex-2-enone (IUPAC name) (903)+TX, farnesol with nerolidol (alternative name) (324)+TX, MB-599 (development code) (498)+TX, MGK 264 (development code) (296)+TX, piperonyl butoxide (649)+TX, piprotal (1343)+TX, propyl isomer (1358)+TX, S421 (development code) (724)+TX, sesamex (1393)+TX, sesasmolin (1394) and sulfoxide (1406)+TX, an animal repellent selected from the group of substances consisting of anthraquinone (32)+TX, chloralose (127)+TX, copper naphthenate [CCN]+TX, copper oxychloride (171)+TX, diazinon (227)+TX, dicyclopentadiene (chemical name) (1069)+TX, guazatine (422)+TX, guazatine acetates (422)+TX, methiocarb (530)+TX, pyridin-4-amine (IUPAC name) (23)+TX, thiram (804)+TX, trimethacarb (840)+TX, zinc naphthenate [CCN] and ziram (856)+TX, a virucide selected from the group of substances consisting of imanin (alternative name) [CCN] and ribavirin (alternative name) [CCN]+TX, a wound protectant selected from the group of substances consisting of mercuric oxide (512)+TX, octhilinone (590) and thiophanate-methyl (802)+TX, and biologically active compounds selected from the group consisting of azaconazole (60207-31-0]+TX, bitertanol [70585-36-3]+TX, bromuconazole [116255-48-2]+TX, cyproconazole [94361-06-5]+TX, difenoconazole [119446-68-3]+TX, diniconazole [83657-24-3]+TX, epoxiconazole [106325-08-0]+TX, fenbuconazole [114369-43-6]+TX, fluquinconazole [136426-54-5]+TX, flusilazole [85509-19-9]+TX, flutriafol [76674-21-0]+TX, hexaconazole [79983-71-4]+TX, imazalil [35554-44-0]+TX, imibenconazole [86598-92-7]+TX, ipconazole [125225-28-7]+TX, metconazole [125116-23-6]+TX, myclobutanil [88671-89-0]+TX, pefurazoate [101903-30-4]+TX, penconazole [66246-88-6]+TX, prothioconazole [178928-70-6]+TX, pyrifenox [88283-41-4]+TX, prochloraz [67747-09-5]+TX, propiconazole [60207-90-1]+TX, simeconazole [149508-90-7]+TX, tebucon-azole [107534-96-3]+TX, tetraconazole [112281-77-3]+TX, triadimefon [43121-43-3]+TX, triadimenol [55219-65-3]+TX, triflumizole [99387-89-0]+TX, triticonazole [131983-72-7]+TX, ancymidol [12771-68-5]+TX, fenarimol [60168-88-9]+TX, nuarimol [63284-71-9]+TX, bupirimate [41483-43-6]+TX, dimethirimol [5221-53-4]+TX, ethirimol [23947-60-6]+TX, dodemorph [1593-77-7]+TX, fenpropidine [67306-00-7]+TX, fenpropimorph [67564-91-4]+TX, spiroxamine [118134-30-8]+TX, tridemorph [81412-43-3]+TX, cyprodinil [121552-61-2]+TX, mepanipyrim [110235-47-7]+TX, pyrimethanil [53112-28-0]+TX, fenpiclonil [74738-17-3]+TX, fludioxonil [131341-86-1]+TX, benalaxyl [71626-11-4]+TX, furalaxyl [57646-30-7]+TX, metalaxyl [57837-19-1]+TX, R-metalaxyl [70630-17-0]+TX, ofurace [58810-48-3]+TX, oxadixyl [77732-09-3]+TX, benomyl [17804-35-2]+TX, carbendazim [10605-21-7]+TX, debacarb [62732-91-6]+TX, fuberidazole [3878-19-1]+TX, thiabendazole [148-79-8]+TX, chlozolinate [84332-86-5]+TX, dichlozoline [24201-58-9]+TX, iprodione [36734-19-7]+TX, myclozoline [54864-61-8]+TX, procymidone [32809-16-8]+TX, vinclozoline [50471-44-8]+TX, boscalid [188425-85-6]+TX, carboxin [5234-68-4]+TX, fenfuram [24691-80-3]+TX, flutolanil [66332-96-5]+TX, mepronil [55814-41-0]+TX, oxycarboxin [5259-88-1]+TX, penthiopyrad [183675-82-3]+TX, thifluzamide [130000-40-7]+TX, guazatine [108173-90-6]+TX, dodine [2439-10-3] [112-65-2] (free base)+TX, iminoctadine [13516-27-3]+TX, azoxystrobin [131860-33-8]+TX, dimoxystrobin [149961-52-4]+TX, enestroburin {Proc. BCPC, Int. Congr., Glasgow, 2003, 1, 93}+TX, fluoxastrobin [361377-29-9]+TX, kresoxim-methyl [143390-89-0]+TX, metominostrobin [133408-50-1]+TX, trifloxystrobin [141517-21-7]+TX, orysastrobin [248593-16-0]+TX, picoxystrobin [117428-22-5]+TX, pyraclostrobin [175013-18-0]+TX, ferbam [14484-64-1]+TX, mancozeb [8018-01-7]+TX, maneb [12427-38-2]+TX, metiram [9006-42-2]+TX, propineb [12071-83-9]+TX, thiram [137-26-8]+TX, zineb [12122-67-7]+TX, ziram [137-30-4]+TX, captafol [2425-06-1]+TX, captan [133-06-2]+TX, dichlofluanid [1085-98-9]+TX, fluoroimide [41205-21-4]+TX, folpet [133-07-3]+TX, tolylfluanid [731-27-1]+TX, bordeaux mixture [8011-63-0]+TX, copperhydroxid [20427-59-2]+TX, copperoxychlorid [1332-40-7]+TX, coppersulfat [7758-98-7]+TX, copperoxid [1317-39-1]+TX, mancopper [53988-93-5]+TX, oxine-copper [10380-28-6]+TX, dinocap [131-72-6]+TX, nitrothal-isopropyl [10552-74-6]+TX, edifenphos [17109-49-8]+TX, iprobenphos [26087-47-8]+TX, isoprothiolane [50512-35-1]+TX, phosdiphen [36519-00-3]+TX, pyrazophos [13457-18-6]+TX, tolclofos-methyl [57018-04-9]+TX, acibenzolar-S-methyl [135158-54-2]+TX, anilazine [101-05-3]+TX, benthiavalicarb [413615-35-7]+TX, blasticidin-S [2079-00-7]+TX, chinomethionat [2439-01-2]+TX, chloroneb [2675-77-6]+TX, chlorothalonil [1897-45-6]+TX, cyflufenamid [180409-60-3]+TX, cymoxanil [57966-95-7]+TX, dichlone [117-80-6]+TX, diclocymet [139920-32-4]+TX, diclomezine [62865-36-5]+TX, dicloran [99-30-9]+TX, diethofencarb [87130-20-9]+TX, dimetho-morph [110488-70-5]+TX, SYP-L190 (Flumorph) [211867-47-9]+TX, dithianon [3347-22-6]+TX, ethaboxam [162650-77-3]+TX, etridiazole [2593-15-9]+TX, famoxadone [131807-57-3]+TX, fenamidone [161326-34-7]+TX, fenoxanil [115852-48-7]+TX, fentin [668-34-8]+TX, ferimzone [89269-64-7]+TX, fluazinam [79622-59-6]+TX, fluopicolide [239110-15-7]+TX, flusulfamide [106917-52-6]+TX, fenhexamid [126833-17-8]+TX, fosetyl-aluminium [39148-24-8]+TX, hymexazol [10004-44-1]+TX, iprovalicarb [140923-17-7]+TX, IKF-916 (Cyazofamid) [120116-88-3]+TX, kasugamycin [6980-18-3]+TX, methasulfocarb [66952-49-6]+TX, metrafenone [220899-03-6]+TX, pencycuron [66063-05-6]+TX, phthalide [27355-22-2]+TX, polyoxins [11113-80-7]+TX, probenazole [27605-76-1]+TX, propamocarb [25606-41-1]+TX, proquinazid [189278-12-4]+TX, pyroquilon [57369-32-1]+TX, quinoxyfen [124495-18-7]+TX, quintozene [82-68-8]+TX, sulfur [7704-34-9]+TX, tiadinil [223580-51-6]+TX, triazoxide [72459-58-6]+TX, tricyclazole [41814-78-2]+TX, triforine [26644-46-2]+TX, validamycin [37248-47-8]+TX, zoxamide (RH7281) [156052-68-5]+TX, mandipropamid [374726-62-2]+TX, isopyrazam [881685-58-1]+TX, sedaxane [874967-67-6]+TX, 3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid (9-dichloromethylene-1,2,3,4-tetrahydro-1,4-methano-naphthalen-5-yl)-amide (disclosed in WO 2007/048556)+TX, 3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid (3′,4′,5′-trifluoro-biphenyl-2-yl)-amide (disclosed in WO 2006/087343)+TX, [(3S,4R,4aR,6S,6aS,12R,12aS,12bS)-3-[(cyclopropylcarbonyl)oxy]-1,3,4,4a,5,6,6a,12,12a,12b-decahydro-6,12-dihydroxy-4,6a,12b-trimethyl-11-oxo-9-(3-pyridinyl)-2H,11Hnaphtho[2,1-b]pyrano[3,4-e]pyran-4-yl]methyl-cyclopropanecarboxylate [915972-17-7]+TX and 1,3,5-trimethyl-N-(2-methyl-1-oxopropyl)-N-[3-(2-methylpropyl)-4-[2,2,2-trifluoro-1-methoxy-1-(trifluoromethyl)ethyl]phenyl]-1H-pyrazole-4-carboxamide [926914-55-8]+TX.

(114) The references in brackets behind the active ingredients, e.g. [3878-19-1] refer to the Chemical Abstracts Registry number. The above described mixing partners are known. Where the active ingredients are included in “The Pesticide Manual” [The Pesticide Manual—A World Compendium; Thirteenth Edition; Editor: C. D. S. TomLin; The British Crop Protection Council], they are described therein under the entry number given in round brackets hereinabove for the particular compound; for example, the compound “abamectin” is described under entry number (1). Where “[CCN]” is added hereinabove to the particular compound, the compound in question is included in the “Compendium of Pesticide Common Names”, which is accessible on the internet [A. Wood; Compendium of Pesticide Common Names, Copyright © 1995-2004]; for example, the compound “acetoprole” is described under the internet address http://www.alanwood.net/pesticides/acetoprole.html.

(115) Most of the active ingredients described above are referred to hereinabove by a so-called “common name”, the relevant “ISO common name” or another “common name” being used in individual cases. If the designation is not a “common name”, the nature of the designation used instead is given in round brackets for the particular compound; in that case, the IUPAC name, the IUPAC/Chemical Abstracts name, a “chemical name”, a “traditional name”, a “compound name” or a “development code” is used or, if neither one of those designations nor a “common name” is used, an “alternative name” is employed. “CAS Reg. No” means the Chemical Abstracts Registry Number.

(116) The active ingredient mixture of the compounds according to any one of embodiments 1 to 12 with active ingredients described above comprises a compound according to any one of embodiments 1 to 12 and an active ingredient as described above preferably in a mixing ratio of from 100:1 to 1:6000, especially from 50:1 to 1:50, more especially in a ratio of from 20:1 to 1:20, even more especially from 10:1 to 1:10, very especially from 5:1 and 1:5, special preference being given to a ratio of from 2:1 to 1:2, and a ratio of from 4:1 to 2:1 being likewise preferred, above all in a ratio of 1:1, or 5:1, or 5:2, or 5:3, or 5:4, or 4:1, or 4:2, or 4:3, or 3:1, or 3:2, or 2:1, or 1:5, or 2:5, or 3:5, or 4:5, or 1:4, or 2:4, or 3:4, or 1:3, or 2:3, or 1:2, or 1:600, or 1:300, or 1:150, or 1:35, or 2:35, or 4:35, or 1:75, or 2:75, or 4:75, or 1:6000, or 1:3000, or 1:1500, or 1:350, or 2:350, or 4:350, or 1:750, or 2:750, or 4:750. Those mixing ratios are by weight.

(117) The mixtures as described above can be used in a method for controlling pests, which comprises applying a composition comprising a mixture as described above 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.

(118) The mixtures comprising a compound of according to any one of embodiments 1 to 12 and one or more active ingredients as described above can be applied, for example, in a single “ready-mix” form, in a combined spray mixture composed from separate formulations of the single active ingredient components, such as a “tank-mix”, and in a combined use of the single active ingredients when applied in a sequential manner, i.e. one after the other with a reasonably short period, such as a few hours or days. The order of applying the compounds according to any one of embodiments 1 to 12 and the active ingredients as described above is not essential for working the present invention.

(119) The compositions according to the invention can also comprise further solid or liquid auxiliaries, such as stabilizers, for example unepoxidized or epoxidized vegetable oils (for example epoxidized coconut oil, rapeseed oil or soya oil), antifoams, for example silicone oil, preservatives, viscosity regulators, binders and/or tackifiers, fertilizers or other active ingredients for achieving specific effects, for example bactericides, fungicides, nematocides, plant activators, molluscicides or herbicides.

(120) The compositions according to the invention are prepared in a manner known per se, in the absence of auxiliaries for example by grinding, screening and/or compressing a solid active ingredient and in the presence of at least one auxiliary for example by intimately mixing and/or grinding the active ingredient with the auxiliary (auxiliaries). These processes for the preparation of the compositions and the use of the compounds I for the preparation of these compositions are also a subject of the invention.

(121) The application methods for the compositions, that is the methods of controlling pests of the abovementioned type, such as spraying, atomizing, dusting, brushing on, dressing, scattering or pouring—which are to be selected to suit the intended aims of the prevailing circumstances—and the use of the compositions for controlling pests of the abovementioned type are other subjects of the invention. Typical rates of concentration are between 0.1 and 1000 ppm, preferably between 0.1 and 500 ppm, of active ingredient. The rate of application per hectare is generally 1 to 2000 g of active ingredient per hectare, in particular 10 to 1000 g/ha, preferably 10 to 600 g/ha.

(122) A preferred method of application in the field of crop protection is application to the foliage of the plants (foliar application), it being possible to select frequency and rate of application to match the danger of infestation with the pest in question. Alternatively, the active ingredient can reach the plants via the root system (systemic action), by drenching the locus of the plants with a liquid composition or by incorporating the active ingredient in solid form into the locus of the plants, for example into the soil, for example in the form of granules (soil application). In the case of paddy rice crops, such granules can be metered into the flooded paddy-field.

(123) The compounds of the invention and compositions thereof are also be suitable for the protection of plant propagation material, for example seeds, such as fruit, tubers or kernels, or nursery plants, against pests of the abovementioned type. The propagation material can be treated with the compound prior to planting, for example seed can be treated prior to sowing. Alternatively, the compound can be applied to seed kernels (coating), either by soaking the kernels in a liquid composition or by applying a layer of a solid composition. It is also possible to apply the compositions when the propagation material is planted to the site of application, for example into the seed furrow during drilling. These treatment methods for plant propagation material and the plant propagation material thus treated are further subjects of the invention. Typical treatment rates would depend on the plant and pest/fungi to be controlled and are generally between 1 to 200 grams per 100 kg of seeds, preferably between 5 to 150 grams per 100 kg of seeds, such as between 10 to 100 grams per 100 kg of seeds.

(124) The term seed embraces seeds and plant propagules of all kinds including but not limited to true seeds, seed pieces, suckers, corns, bulbs, fruit, tubers, grains, rhizomes, cuttings, cut shoots and the like and means in a preferred embodiment true seeds.

(125) The present invention also comprises seeds coated or treated with or containing a compound according to any one of embodiments 1 to 12. The term “coated or treated with and/or containing” generally signifies that the active ingredient is for the most part on the surface of the seed at the time of application, although a greater or lesser part of the ingredient may penetrate into the seed material, depending on the method of application. When the said seed product is (re)planted, it may absorb the active ingredient. In an embodiment, the present invention makes available a plant propagation material adhered thereto with according to any one of embodiments 1 to 12. Further, it is hereby made available, a composition comprising a plant propagation material treated with a compound according to any one of embodiments 1 to 12.

(126) Seed treatment comprises all suitable seed treatment techniques known in the art, such as seed dressing, seed coating, seed dusting, seed soaking and seed pelleting. The seed treatment application of the compound according to any one of embodiments 1 to 12 can be carried out by any known methods, such as spraying or by dusting the seeds before sowing or during the sowing/planting of the seeds.

(127) The pesticidal/insecticidal properties of the compounds according to any one of embodiments 1 to 12 can be illustrated via the following tests:

(128) Diabrotica balteata (Corn Root Worm):

(129) 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 4 days after infestation. The following compounds resulted in at least 80% mortality at an application rate of 200 ppm: 1, 2, 3, 4, 10, 11, 12, 13, 14 and 15.

(130) Euschistus heros (Neotropical Brown Stink Bug): Feeding/Contact Activity

(131) 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 5 days after infestation. The following compounds resulted in at least 80% mortality at an application rate of 200 ppm: 1, 2, 3, 4, 5, 6, 7, 8, 9, 10 and 12.

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

(133) 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. The following compounds resulted in at least 80% mortality at an application rate of 200 ppm: 1, 2, 4, 5 and 8.

(134) Plutella xylostella (Diamond Back Moth): Feeding/Contact Activity

(135) 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 5 days after infestation. The following compounds resulted in at least 80% mortality at an application rate of 200 ppm: 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14 and 15.

(136) Spodoptera littoralis (Egyptian Cotton Leaf Worm): Feeding/Contact Activity

(137) 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 3 days after infestation. The following compounds resulted in at least 80% mortality at an application rate of 200 ppm: 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15 and 16.

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

(139) 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. The following compounds resulted in at least 80% mortality at an application rate of 200 ppm: 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11 and 12.

(140) Thrips tabaci (Onion Thrips): Feeding/Contact Activity

(141) 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: 1, 2, 3, 4, 10, 11, 12, 13, 14, 15 and 16.

(142) The compounds of the invention can be distinguished from known compounds by virtue of greater efficacy at low application rates, which can be verified by the person skilled in the art using the experimental procedures outlined in the Examples, using lower application rates if necessary, for example 50 ppm, 12.5 ppm, δ ppm, 3 ppm, 1.5 ppm, 0.8 ppm or 0.2 ppm.

(143) Furthermore, besides of the insecticidal properties, the compounds according to any one of embodiments 1 to 12 have surprisingly shown to have improved degradation properties compared with prior art compounds. Additionally, the compounds according to any one of embodiments 1 to 12 have surprisingly shown to be less toxic to the environment, e.g. to bees or aquatic organisms, compared with prior art compounds.