PESTICIDALLY ACTIVE HETEROCYCLIC DERIVATIVES WITH SULFUR CONTAINING SUBSTITUENTS

Abstract

Compounds of the formula (I) wherein the substituents are as defined in claim 1. Furthermore, the present invention relates to agrochemical compositions which comprise compounds of formula (I), to preparation of these compositions, and to the use of the compounds or compositions 10 in agriculture or horticulture for combating, preventing or controlling animal pests, including arthropods and in particular insects or representatives of the order Acarina.

##STR00001##

Claims

1. A compound of formula (I) ##STR00169## wherein A is CH or N; X is S, SO or SO.sub.2; R.sub.1 is C.sub.1-C.sub.4alkyl, C.sub.1-C.sub.4haloalkyl or C.sub.3-C.sub.6cycloalkyl-C.sub.1-C.sub.4alkyl; R.sub.2 is halogen, C.sub.1-C.sub.6haloalkyl, C.sub.1-C.sub.4haloalkylsulfanyl, C.sub.1-C.sub.4haloalkylsulfinyl, C.sub.1-C.sub.4haloalkylsulfonyl or C.sub.1-C.sub.6haloalkoxy; R.sub.3 is hydrogen, C.sub.1-C.sub.6alkyl, C.sub.2-C.sub.6alkenyl, C.sub.1-C.sub.6haloalkyl, C.sub.1-C.sub.6alkoxy, C.sub.1-C.sub.6haloalkoxy, C.sub.1-C.sub.6cyanoalkyl, C.sub.1-C.sub.6hydroxyalkyl, C.sub.1-C.sub.6alkoxycarbonyl, C.sub.1-C.sub.4alkoxy-C.sub.1-C.sub.4alkyl, C.sub.1-C.sub.4alkylthio-C.sub.1-C.sub.4alkyl, C.sub.1-C.sub.4alkylsulfinyl-C.sub.1-C.sub.4alkyl, C.sub.1-C.sub.4alkylsulfonyl-C.sub.1-C.sub.4alkyl, C.sub.3-C.sub.6cycloalkyl-C.sub.1-C.sub.4alkyl, C.sub.3-C.sub.6halocycloalkyl-C.sub.1-C.sub.4alkyl, C.sub.3-C.sub.6cycloalkyl or C.sub.3-C.sub.6cycloalkyl substituted by a substituent selected from cyano, halogen, C.sub.1-C.sub.3haloalkyl, CO.sub.2H, CONH.sub.2, C.sub.1-C.sub.6alkylaminocarbonyl, C.sub.1-C.sub.6dialkylaminocarbonyl or C.sub.1-C.sub.4alkoxycarbonyl; R.sub.4 is C.sub.1-C.sub.6alkyl, C.sub.2-C.sub.6alkenyl, C.sub.1-C.sub.6haloalkyl, C.sub.1-C.sub.6hydroxyalkyl, C.sub.1-C.sub.4alkoxy-C.sub.1-C.sub.4alkyl, C.sub.1-C.sub.4alkylthio-C.sub.1-C.sub.4alkyl, C.sub.1-C.sub.4alkylsulfinyl-C.sub.1-C.sub.4alkyl, C.sub.1-C.sub.4alkylsulfonyl-C.sub.1-C.sub.4alkyl, C.sub.3-C.sub.6cycloalkyl-C.sub.1-C.sub.2alkyl, C.sub.1-C.sub.6cyanoalkyl, C.sub.3-C.sub.6cycloalkyl or C.sub.3-C.sub.6cycloalkyl which is mono- or poly-substituted by substituents selected from the group consisting of halogen, cyano, C.sub.1-C.sub.3haloalkyl, CO.sub.2H, CONH.sub.2, C.sub.1-C.sub.6alkylaminocarbonyl, C.sub.1-C.sub.6dialkylaminocarbonyl and C.sub.1-C.sub.4alkoxycarbonyl; or R.sub.4 is a four- to six-membered heterocyclic ring system which can be partially saturated or fully saturated, said ring system contains 1 to 2 ring heteroatoms selected from O, N, or S(O)n, wherein n is 0, 1 or 2 providing that the heterocyclic ring system does not contain adjacent oxygen atoms, adjacent sulphur atoms, or adjacent sulphur and oxygen atoms and that the ring nitrogen, when present, may be substituted by hydrogen or C.sub.1-C.sub.4 alkyl, and said ring system can be optionally mono- or di-substituted from the group consisting of halogen, cyano, C.sub.1-C.sub.4alkyl, C.sub.1-C.sub.4alkoxy, C.sub.1-C.sub.4haloalkyl or oxo; or R.sub.3 and R.sub.4 together with the NC(O) fragment to which they are attached form a 5- or 6-membered saturated five or six membered ring system which may contain one or two additional ring heteroatoms selected from O, N, or S(O)n, wherein n is 0, 1 or 2, providing that the heterocyclic ring system does not contain adjacent oxygen atoms, adjacent sulphur atoms, or adjacent sulphur and oxygen atoms and that the additional ring nitrogen, when present, is substituted by hydrogen or C.sub.1-C.sub.4 alkyl, C.sub.1-C.sub.4alkoxy, or C.sub.1-C.sub.4haloalkoxy, and wherein the ring system can be optionally mono- or di-substituted with substituents independently selected from halogen, cyano, C.sub.1-C.sub.4alkyl, C.sub.1-C.sub.4alkoxy, C.sub.1-C.sub.4haloalkyl or oxo; and X.sub.1 is O, S or NRs; wherein R.sub.5 is hydrogen or C.sub.1-C.sub.4alkyl; or an agrochemically acceptable salt, stereoisomer, enantiomer, tautomer or N-oxide of a compound of formula (I).

2. A compound, or an agrochemically acceptable salt, stereoisomer, enantiomer, tautomer or N-oxide thereof, according to claim 1 wherein R.sub.4 is C.sub.1-C.sub.6alkyl, C.sub.2-C.sub.6alkenyl, C.sub.1-C.sub.6haloalkyl, C.sub.1-C.sub.6hydroxyalkyl, C.sub.1-C.sub.4alkoxy-C.sub.1-C.sub.4alkyl, C.sub.1-C.sub.4alkylthio-C.sub.1-C.sub.4alkyl, C.sub.1-C.sub.4alkylsulfinyl-C.sub.1-C.sub.4alkyl, C.sub.1-C.sub.4alkylsulfonyl-C.sub.1-C.sub.4alkyl, C.sub.3-C.sub.6cycloalkyl-C.sub.1-C.sub.2alkyl, C.sub.1-C.sub.6cyanoalkyl, C.sub.3-C.sub.6cycloalkyl or C.sub.3-C.sub.6cycloalkyl which is mono- or poly-substituted by substituents selected from the group consisting of halogen, cyano, C.sub.1-C.sub.3haloalkyl, CO.sub.2H, CONH.sub.2, C.sub.1-C.sub.6alkylaminocarbonyl, C.sub.1-C.sub.6dialkylaminocarbonyl and C.sub.1-C.sub.4alkoxycarbonyl.

3. A compound, or an agrochemically acceptable salt, stereoisomer, enantiomer, tautomer or N-oxide thereof, according to claim 1 wherein R.sub.4 is a four- to six-membered heterocyclic ring system which can be partially saturated or fully saturated, said ring system contains 1 to 2 ring heteroatoms selected from O, N, or S(O)n, wherein n is 0, 1 or 2 providing that the heterocyclic ring system does not contain adjacent oxygen atoms, adjacent sulphur atoms, or adjacent sulphur and oxygen atoms and the nitrogen, when present, may be substituted by hydrogen or C.sub.1-C.sub.4 alkyl, and said ring system can be optionally mono- or di-substituted from the group consisting of halogen, cyano, C.sub.1-C.sub.4alkyl, C.sub.1-C.sub.4alkoxy, C.sub.1-C.sub.4haloalkyl or oxo.

4. A compound, or an agrochemically acceptable salt, stereoisomer, enantiomer, tautomer or N-oxide thereof, according to claim 1 wherein R.sub.3 and R.sub.4 together with the NC(O) fragment to which they are attached form a 5- or 6-membered saturated five or six membered ring system which may contain one or two additional ring heteroatoms selected from O, N, or S(O)n, wherein n is 0, 1 or 2, providing that the heterocyclic ring system does not contain adjacent oxygen atoms, adjacent sulphur atoms, or adjacent sulphur and oxygen atoms and that the additional ring nitrogen, when present, is substituted by hydrogen, C.sub.1-C.sub.4 alkyl or C.sub.1-C.sub.4alkoxy, and wherein the ring system can be optionally mono- or di-substituted with substituents independently selected from halogen, cyano, C.sub.1-C.sub.4alkyl, C.sub.1-C.sub.4alkoxy, C.sub.1-C.sub.4haloalkyl or oxo.

5. A compound, or an agrochemically acceptable salt, stereoisomer, enantiomer, tautomer or N-oxide thereof, according to claim 1 wherein R.sub.1 is ethyl or cyclopropylmethyl.

6. A compound, or an agrochemically acceptable salt, stereoisomer, enantiomer, tautomer or N-oxide thereof, according to claim 1 wherein R.sub.2 is C.sub.1-C.sub.4haloalkyl, C.sub.1-C.sub.4haloalkylsulfanyl, C.sub.1-C.sub.4haloalkylsulfinyl or C.sub.1-C.sub.4haloalkylsulfonyl.

7. A compound, or an agrochemically acceptable salt, stereoisomer, enantiomer, tautomer or N-oxide thereof, according to claim 1 wherein R.sub.3 is hydrogen, C.sub.1-C.sub.6alkyl, C.sub.1-C.sub.6haloalkyl, C.sub.1-C.sub.6alkoxy or C.sub.3-C.sub.6cycloalkyl.

8. A compound, or an agrochemically acceptable salt, stereoisomer, enantiomer, tautomer or N-oxide thereof, according to claim 1 wherein R.sub.4 is C.sub.1-C.sub.6alkyl, C.sub.1-C.sub.6haloalkyl, C.sub.1-C.sub.6hydroxyalkyl, C.sub.1-C.sub.4alkoxy-C.sub.1-C.sub.4alkyl, C.sub.1-C.sub.4alkylthio-C.sub.1-C.sub.4alkyl, C.sub.1-C.sub.4alkylsulfinyl-C.sub.1-C.sub.4alkyl, C.sub.1-C.sub.4alkylsulfonyl-C.sub.1-C.sub.4alkyl or C.sub.3-C.sub.6cycloalkyl.

9. A compound, or an agrochemically acceptable salt, stereoisomer, enantiomer, tautomer or N-oxide thereof, according to claim 1 wherein R.sub.3 and R.sub.4 together with the NC(O) fragment to which they are attached form substituent Qa, which is a radical selected from Qa1 to Qa15 ##STR00170## ##STR00171## ##STR00172## where the arrow shows the attachment point to the phenyl or pyridyl ring, and wherein each ring system can be mono- or di-substituted by substituents selected from the group consisting of halogen, cyano, C.sub.1-C.sub.4alkyl, C.sub.1-C.sub.4alkoxy, and C.sub.1-C.sub.4haloalkyl; wherein Rea is hydrogen, C.sub.1-C.sub.4alkyl, C.sub.1-C.sub.4alkoxy, or C.sub.1-C.sub.4haloalkoxy.

10. A compound, or an agrochemically acceptable salt, stereoisomer, enantiomer, tautomer or N-oxide thereof, according to claim 1 wherein X.sub.1 is NRs, where R.sub.5 is C.sub.1-C.sub.4alkyl (preferably NRs is NCH.sub.3); X is S or SO.sub.2; R.sub.1 is ethyl; and R.sub.2 is C.sub.1-C.sub.4haloalkyl (preferably trifluoromethyl).

11. A compound according to claim 1 wherein A is CH or N; X is S or SO.sub.2; R.sub.1 is ethyl or cyclopropylmethyl; R.sub.2 is C.sub.1-C.sub.4haloalkyl; R.sub.3 is hydrogen, C.sub.1-C.sub.6alkyl, C.sub.1-C.sub.6haloalkyl, C.sub.1-C.sub.6alkoxy or C.sub.3-C.sub.6cycloalkyl; R.sub.4 is C.sub.1-C.sub.6alkyl, C.sub.1-C.sub.6haloalkyl, C.sub.1-C.sub.6hydroxyalkyl, C.sub.1-C.sub.4alkoxy-C.sub.1-C.sub.4alkyl, C.sub.1-C.sub.4alkylthio-C.sub.1-C.sub.4alkyl, C.sub.1-C.sub.4alkylsulfinyl-C.sub.1-C.sub.4alkyl, C.sub.1-C.sub.4alkylsulfonyl-C.sub.1-C.sub.4alkyl or C.sub.3-C.sub.6cycloalkyl; or R.sub.3 and R.sub.4 together with the NC(O) fragment to which they are attached form substituent Qa, which is a radical selected from Qa1 to Qa15 ##STR00173## ##STR00174## ##STR00175## where the arrow shows the attachment point to the phenyl or pyridyl ring, and wherein each ring system can be mono- or di-substituted by substituents selected from the group consisting of halogen, cyano, C.sub.1-C.sub.4alkyl, C.sub.1-C.sub.4alkoxy, and C.sub.1-C.sub.4haloalkyl; wherein R.sub.2a is hydrogen, C.sub.1-C.sub.4alkyl, C.sub.1-C.sub.4alkoxy, or C.sub.1-C.sub.4haloalkoxy; and X.sub.1 is NR.sub.5; wherein R.sub.5 is C.sub.1-C.sub.4alkyl; or an agrochemically acceptable salt, stereoisomer, enantiomer, tautomer or N-oxide thereof.

12. A compound, or an agrochemically acceptable salt, stereoisomer, enantiomer, tautomer or N-oxide thereof, according to claim 1 wherein A is N.

13. A compound of formula I according to claim 1, represented by the compounds of formula I-1 ##STR00176## wherein A, X, R.sub.1, R.sub.2, R.sub.3, and X.sub.1 are as defined under formula I in claim 1; and wherein Rao is C.sub.1-C.sub.6alkyl, C.sub.1-C.sub.6haloalkyl, C.sub.1-C.sub.6hydroxyalkyl, C.sub.1-C.sub.4alkoxy-C.sub.1-C.sub.4alkyl, C.sub.1-C.sub.4alkylthio-C.sub.1-C.sub.4alkyl, C.sub.1-C.sub.4alkylsulfinyl-C.sub.1-C.sub.4alkyl, C.sub.1-C.sub.4alkylsulfonyl-C.sub.1-C.sub.4alkyl, C.sub.1-C.sub.6cyanoalkyl, C.sub.3-C.sub.6cycloalkyl or C.sub.3-C.sub.6cycloalkyl mono-substituted by cyano; or an agrochemically acceptable salt, stereoisomer, enantiomer, tautomer or N-oxide thereof.

14. A compound of formula I according to claim 1, represented by the compounds of formula I-1-1 ##STR00177## wherein A, X, R.sub.1, R.sub.2, R.sub.4, and X.sub.1 are as defined under formula I in claim 1; and wherein Rai is hydrogen, C.sub.1-C.sub.6alkyl, C.sub.1-C.sub.6haloalkyl, C.sub.1-C.sub.6alkoxy, C.sub.3-C.sub.6cycloalkyl or C.sub.3-C.sub.6cycloalkyl mono-substituted by cyano: or an agrochemically acceptable salt, stereoisomer, enantiomer, tautomer or N-oxide thereof.

15. A compound of formula I according to claim 1, represented by the compounds of formula I-3 ##STR00178## wherein A, X, R.sub.1, R.sub.2 and X.sub.1 are as defined under formula I in claim 1; and wherein Rc.sub.3 and Rc.sub.4 together with the NC(O) fragment to which they are attached form substituent Qa, which is a radical selected from Qa2, Qa3, Qa5, Qa6, Qa7, Qa8 and Qa8*, ##STR00179## where the arrow shows the attachment point to the phenyl or pyridyl ring; and wherein R.sub.2a is hydrogen, C.sub.1-C.sub.4alkyl or C.sub.1-C.sub.4alkoxy; preferably R.sub.2a is hydrogen, methyl or methoxy; or an agrochemically acceptable salt, stereoisomer, enantiomer, tautomer or N-oxide thereof.

16. A compound, or an agrochemically acceptable salt, stereoisomer, enantiomer, tautomer or N-oxide thereof, according to claim 13 wherein X.sub.1 is NRs, where R.sub.5 is C.sub.1-C.sub.4alkyl (preferably NR.sub.5 is NCH.sub.3); X is S or SO.sub.2; R.sub.1 is ethyl; R.sub.2 is C.sub.1-C.sub.4haloalkyl (preferably trifluoromethyl) and A is N.

17. A compound of formula I according to claim 1, selected from the group consisting of: N-[5-ethyl sulfanyl-6-[3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridin-2-yl]-3-pyridyl]cyclopropanecarboxamide (compound P1); N-[5-ethylsulfonyl-6-[3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridin-2-yl]-3-pyridyl]cyclopropanecarboxamide (compound P2); N-[3-ethylsulfonyl-4-[3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridin-2-yl]phenyl]-2,2,2-trifluoro-acetamide (compound P3); N-[5-ethylsulfonyl-6-[3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridin-2-yl]-3-pyridyl]acetamide; (compound P4); 1-[5-ethylsulfonyl-6-[3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridin-2-yl]-3-pyridyl]pyrrolidin-2-one (compound P5); N-[5-ethylsulfonyl-6-[3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridin-2-yl]-3-pyridyl]-N-methyl-acetamide (compound P6); N-[5-ethyl sulfanyl-6-[3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridin-2-yl]-3-pyridyl]-2-hydroxy-2-methyl-propanamide (compound P7); N-[5-ethylsulfonyl-6-[3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridin-2-yl]-3-pyridyl]-2-hydroxy-2-methyl-propanamide (compound P8); N-[5-ethylsulfonyl-6-[3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridin-2-yl]-3-pyridyl]-N-methyl-cyclopropanecarboxamide (compound P9); N-cyclopropyl-N-[5-ethylsulfonyl-6-[3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridin-2-yl]-3-pyridyl]acetamide (compound P10); N-[5-ethylsulfonyl-6-[3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridin-2-yl]-3-pyridyl]-2,2,2-trifluoro-N-methyl-acetamide (compound P11); N-[5-ethylsulfonyl-6-[3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridin-2-yl]-3-pyridyl]-2-methoxy-N-methyl-acetamide (compound P12); N-[5-ethylsulfonyl-6-[3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridin-2-yl]-3-pyridyl]-2,2-difluoro-N-methyl-acetamide (compound P13); N-[5-ethylsulfonyl-6-[3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridin-2-yl]-3-pyridyl]-N-methyl-2-methyl sulfanyl-acetamide (compound P14); 4-[5-ethylsulfonyl-6-[3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridin-2-yl]-3-pyridyl]morpholin-3-one (compound P15); N-[3-ethylsulfonyl-4-[3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridin-2-yl]phenyl]-N-methyl-acetamide (compound P16); N-[5-ethylsulfonyl-6-[3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridin-2-yl]-3-pyridyl]-N-methyl-2-methylsulfonyl-acetamide (compound P17); 4-[5-ethylsulfonyl-6-[3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridin-2-yl]-3-pyridyl]-1,1-dioxo-1,4-thiazinan-3-one (compound P18); 4-[5-ethylsulfonyl-6-[3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridin-2-yl]-3-pyridyl]thiomorpholin-3-one (compound P19); 2-chloro-N-ethyl-N-[5-ethylsulfonyl-6-[3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridin-2-yl]-3-pyridyl]acetamide (compound P20); N-ethyl-N-[5-ethylsulfonyl-6-[3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridin-2-yl]-3-pyridyl]acetamide (compound P21); 2-chloro-N-[5-ethylsulfonyl-6-[3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridin-2-yl]-3-pyridyl]-N-methyl-acetamide (compound P22); N-[5-ethylsulfonyl-6-[3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridin-2-yl]-3-pyridyl]-N-methyl-propanamide (compound P23); N-[5-ethylsulfonyl-6-[3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridin-2-yl]-3-pyridyl]-N-methoxy-cyclopropanecarboxamide (compound P24); N-[5-ethylsulfonyl-6-[3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridin-2-yl]-3-pyridyl]propanamide (compound P25); N-[5-ethylsulfonyl-6-[3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridin-2-yl]-3-pyridyl]-N,2,2-trimethyl-propanamide (compound P26); N-[5-ethylsulfonyl-6-[3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridin-2-yl]-3-pyridyl]-N,2-dimethyl-propanamide (compound P27); N-[5-ethylsulfonyl-6-[3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridin-2-yl]-3-pyridyl]-3,3,3-trifluoro-N-methyl-propanamide (compound P28); N-[5-ethylsulfonyl-6-[3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridin-2-yl]-3-pyridyl]-N-methoxy-propanamide (compound P29); N-[5-ethylsulfonyl-6-[3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridin-2-yl]-3-pyridyl]-N-methoxy-acetamide (compound P30); N-[5-ethylsulfonyl-6-[3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridin-2-yl]-3-pyridyl]-N-methyl-3-methylsulfonyl-propanamide (compound P31); N-[5-ethylsulfonyl-6-[3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridin-2-yl]-3-pyridyl]-N-(2,2,2-trifluoroethyl)propanamide (compound P32); N-[5-ethyl sulfanyl-6-[3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridin-2-yl]-3-pyridyl]-N-methyl-acetamide (compound P33); 3-[5-ethylsulfonyl-6-[3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridin-2-yl]-3-pyridyl]oxazolidin-2-one (compound P34); 1-[5-ethylsulfonyl-6-[3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridin-2-yl]-3-pyridyl]-3-methoxy-imidazolidin-2-one (compound P35); 1-[5-ethylsulfonyl-6-[3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridin-2-yl]-3-pyridyl]imidazolidin-2-one (compound P36); 1-[5-ethylsulfonyl-6-[3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridin-2-yl]-3-pyridyl]-3-methyl-imidazolidin-2-one (compound P37); 1-cyano-N-[5-ethylsulfonyl-6-[3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridin-2-yl]-3-pyridyl]-N-methyl-cyclopropanecarboxamide (compound P38); N-[5-ethylsulfonyl-6-[3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridin-2-yl]-3-pyridyl]-2,2-dimethyl-propanamide (compound P39); N-cyclopropyl-N-[5-ethylsulfonyl-6-[3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridin-2-yl]-3-pyridyl]propanamide (compound P40); N-[5-ethylsulfonyl-6-[3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridin-2-yl]-3-pyridyl]-N-methyl-3-methyl sulfanyl-propanamide (compound P41); N-(1-cyanocyclopropyl)-N-[5-ethylsulfonyl-6-[3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridin-2-yl]-3-pyridyl]acetamide (compound P42); 2-cyano-N-[5-ethylsulfonyl-6-[3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridin-2-yl]-3-pyridyl]-N,2-dimethyl-propanamide (compound P43); N-[5-ethylsulfonyl-6-[3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridin-2-yl]-3-pyridyl]-2,2,2-trifluoro-acetamide (compound P44); 3-[5-ethylsulfonyl-6-[3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridin-2-yl]-3-pyridyl]thiazolidin-2-one (compound P45); N-[5-ethylsulfonyl-6-[3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridin-2-yl]-3-pyridyl]-N-isopropyl-acetamide (compound P46); and N-[5-ethyl sulfanyl-6-[3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridin-2-yl]-3-pyridyl]-N-isopropyl-acetamide (compound P47.)

18. A composition comprising an insecticidally, acaricidally, nematicidally or molluscicidally effective amount of a compound of formula (I), or an agrochemically acceptable salt, stereoisomer, enantiomer, tautomer or N-oxide thereof, as defined in claim 1 and, optionally, an auxiliary or diluent.

19. A method of combating and controlling insects, acarines, nematodes or molluscs which comprises applying to a pest, to a locus of a pest, or to a plant susceptible to attack by a pest an insecticidally, acaricidally, nematicidally or molluscicidally effective amount of a compound of formula (I), or an agrochemically acceptable salt, stereoisomer, enantiomer, tautomer or N-oxide thereof, as defined in claim 1.

20. A method for the protection of plant propagation material from the attack by insects, acarines, nematodes or molluscs, which comprises treating the propagation material or the site, where the propagation material is planted, with a composition according to claim 18.

Description

PREPARATORY EXAMPLES

[0444] Mp means melting point in C. Free radicals represent methyl groups. .sup.1H NMR measurements were recorded on a Brucker 400 MHz spectrometer, chemical shifts are given in ppm relevant to a TMS standard. Spectra measured in deuterated solvents as indicated. Either one of the LCMS methods below was used to characterize the compounds. The characteristic LCMS values obtained for each compound were the retention time (Rt, recorded in minutes) and the measured molecular ion (M+H).sup.+.

[0445] LCMS and GCMS Methods:

[0446] Method 1:

[0447] Spectra were recorded on a Mass Spectrometer from Agilent Technologies (6410 Triple Quadruple Mass Spectrometer) equipped with an electrospray source (Polarity: Positive and Negative Polarity Switch, Capillary: 4.00 kV, Fragmentor: 100.00 V, Gas Temperature: 350 C., Gas Flow: 11 L/min, Nebulizer Gas: 45 psi, Mass range: 110-1000 Da, DAD Wavelength range: 210-400 nm). Column: KINETEX EVO C18, length 50 mm, diameter 4.6 mm, particle size 2.6 m. Column oven temperature 40 C. Solvent gradient: A=Water with 0.1% formic acid:Acetonitrile (95:5 v/v). B=Acetonitrile with 0.1% formic acid. Gradient=0 min 90% A, 10% B; 0.9-1.8 min 0% A, 100% B, 2.2-2.5 min 90% A, 10% B. Flow rate 1.8 mL/min.

[0448] Method 2:

[0449] Spectra were recorded on a Mass Spectrometer from Waters (Acquity SDS Mass Spectrometer) equipped with an electrospray source (Polarity: Positive and Negative Polarity Switch, Capillary: 3.00 kV, Cone Voltage: 41.00 V, Source temperature: 150 C., Desolvation Gas Flow: 1000 L/Hr, Desolvation temperature: 500 C., Gas Flow @Cone: 50 L/hr, Mass range: 110-800 Da, PDA wavelength range: 210-400 nm.Column: Acquity UPLC HSS T3 C18, length 30 mm, diameter 2.1 mm, particle size 1.8 m. Column oven temperature 40 C. Solvent gradient: A=Water with 0.1% formic acid: Acetonitrile (95:5 v/v). B=Acetonitrile with 0.05% formic acid. Gradient=0 min 90% A, 10% B; 0.2 min 50% A, 50% B; 0.7-1.3 min 0% A, 100% B; 1.4-1.6 min 90% A, 10% B. Flow rate 0.6 mL/min.

Example H1: Preparation of N-[5-ethylsulfonyl-6-[3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridin-2-yl]-3-pyridyl]-N-methyl-2-methylsulfanyl-acetamide (compound P14, Table P)

[0450] ##STR00081##

Step A: Preparation of tert-butyl N-[5-ethylsulfonyl-6-[3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridin-2-yl]-3-pyridyl]carbamate

[0451] ##STR00082##

[0452] To a solution of 2-(5-bromo-3-ethylsulfonyl-2-pyridyl)-3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridine (1500 mg, 3.339 mmol, prepared as described in WO 2016/005263) in 1,4-dioxane (8 g) was added tert-butyl carbamate (474 mg, 4,007 mmol), cesium carbonate (1.52 g, 4,675 mmol) and XPhos (286 mg, 0.6011 mmol). The reaction mixture was degassed for 10 minutes with argon and then palladium(II) acetate (45 mg, 0.2004 mmol) was added. The reaction mixture was heated at 110 C. for 45 minutes under microwave conditions. The mixture obtained was diluted with ethylacetate and filtered. The organic layer was washed with water and brine, dried over sodium sulfate, filtered and evaporated to afford tert-butyl N-[5-ethylsulfonyl-6-[3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridin-2-yl]-3-pyridyl]carbamate.

[0453] LCMS (method 1): 486 (M+H), Rt 1.03 min.

[0454] .sup.1H NMR (400 MHz, CDCl.sub.3) ppm 1.38 (t, J=7.34 Hz, 3H) 1.58 (s, 9H) 3.80 (q, J=7.46 Hz, 2H) 3.89 (s, 3H) 7.65-7.71 (m, 1H) 8.12 (s, 1H) 8.63 (d, J=2.20 Hz, 1H) 8.97-8.98 (m, 1H) 9.04-9.13 (m, 1H).

Step B: Preparation of tert-butyl N-[5-ethylsulfonyl-6-[3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridin-2-yl]-3-pyridyl]-N-methyl-carbamate

[0455] ##STR00083##

[0456] To a stirred solution of tert-butyl N-[5-ethylsulfonyl-6-[3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridin-2-yl]-3-pyridyl]carbamate (15 g, 30.90 mmol) in N,N-dimethylformamide (150 mL) were added potassium carbonate (5,124 g, 37.08 mmol) and iodomethane (2.32 mL, 37.08 mmol) at room temperature. Reaction mixture was stirred room temperature overnight and then quenched with ice cold water (200 ml). The desired compound was precipitated out. The precipitate was filtered on buchner funnel, washed with water (100 mL), n-pentane (50 mL) and then dried on high vacuum to afford tert-butyl N-[5-ethylsulfonyl-6-[3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridin-2-yl]-3-pyridyl]-N-methyl-carbamate as a white solid.

[0457] LCMS (method 2): Rt 1.52 min, 500 (M+H).

[0458] .sup.1H NMR (400 MHz, CDCl.sub.3) ppm 1.35-1.42 (m, 3H) 1.51 (s, 9H) 3.45 (s, 3H) 3.77-3.85 (m, 2H) 3.90 (s, 3H) 8.11 (s, 1H) 8.43-8.47 (m, 1H) 8.96 (s, 1H) 8.99-9.04 (m, 1H).

Step D: Preparation of 5-ethylsulfonyl-N-methyl-6-[3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridin-2-yl]pyridin-3-amine

[0459] ##STR00084##

[0460] tert-butyl N-[5-ethylsulfonyl-6-[3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridin-2-yl]-3-pyridyl]-N-methyl-carbamate (7 g, 14.01 mmol) was dissolved in dichloromethane (100 mL) and 2,2,2-trifluoroacetic acid (20 mL) was added and gas formation was observed. The reaction was stirred overnight. The solvent was removed and the mixture was neutralized using a saturated solution of potassium carbonate. The precipitate formed was filtered, washed with water and cyclohexane and then dried under reduced pressure to afford 5-ethylsulfonyl-N-methyl-6-[3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridin-2-yl]pyridin-3-amine.

[0461] LCMS (method 2): Rt: 0.85 min, 401(M+H).

[0462] 1H NMR (400 MHz, CDCl.sub.3) ppm 1.37 (t, J=7.46 Hz, 3H) 3.05 (s, 3H) 3.74 (q, J=7.42 Hz, 2H) 3.87 (s, 3H) 5.32 (s, 1H) 7.55 (d, J=2.81 Hz, 1H) 8.13 (s, 1H) 8.30 (d, J=2.69 Hz, 1H) 8.98 (s, 1H).

Step E: Preparation of N-[5-ethylsulfonyl-6-[3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridin-2-yl]-3-pyridyl]-N-methyl-2-methylsulfanyl-acetamide (compound P14, Table P)

[0463] ##STR00085##

[0464] To a colourless clear solution of 2-methylsulfanylacetic acid (0.4 mL, 4.7 mmol), in dichloromethane (5 mL) and one drop of N,N-dimethylformamide (catalytic amount), oxalyl dichloride (0.62 mL, 7 mmol) was added dropwise at cool temperature. The resulting mixture was stirred at room temperature 1 hour, until completion. The reaction mixture was evaporated under reduced pressure at room temperature to afford 2-methylsulfanylacetyl chloride. Under nitrogen, 5-ethylsulfonyl-N-methyl-6-[3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridin-2-yl]pyridin-3-amine (0.5 g, 1.3 mmol) was dissolved in tetrahydrofuran (5 mL), N,N-diethylethanamine (0.21 mL, 1.5 mmol) was added and the resulting mixture was cooled down at 0 C. A solution of 2-methylsulfanylacetyl chloride (0.16 g, 1.3 mmol), dissolved in tetrahydrofuran (3 mL) and added dropwise to the solution. The reaction mixture was stirred at room temperature for 16 hours, then poured into cool water (30 ml). The resulting solution was extracted with ethyl acetate and the combined organic layers were washed with aqueous saturated sodium chloride solution (30 ml), dried over anhydrous sodium sulfate, and concentrated of under reduced pressure. The crude was purified by chromatography over silica gel to afford N-[5-ethylsulfonyl-6-[3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridin-2-yl]-3-pyridyl]-N-methyl-2-methylsulfanyl-acetamide.

[0465] LCMS (method 2): Rt: 0.94 min, 488 (M+H).

[0466] 1H NMR (400 MHz, CDCl.sub.3) ppm 1.35-1.46 (m, 3H) 2.29 (s, 3H) 3.20-3.47 (m, 2H) 3.56 (br s, 3H) 3.81-3.96 (m, 5H) 8.01-8.25 (m, 1H) 8.36-8.58 (m, 1H) 8.87-9.18 (m, 2H).

Example H2: Preparation of N-[5-ethylsulfonyl-6-[3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridin-2-yl]-3-pyridyl]-N-methyl-2-methylsulfonyl-acetamide (Example P17, Table P)

[0467] ##STR00086##

[0468] To a clear, colourless solution of N-[5-ethylsulfonyl-6-[3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridin-2-yl]-3-pyridyl]-N-methyl-2-methylsulfanyl-acetamide (0.31 mmol, 0.15 g) in dichloromethane (2 mL) at 0 C., 3-chlorobenzenecarboperoxoic acid (0.68 mmol, 0.12 g) was added slowly. After 15 minutes reaction mixture was warm up at room temperature and stirred for 2 hours. After completion, the reaction mixture was quenched by addition of aqueous saturated sodium bicarbonate solution. The resulting mixture was extracted with dichloromethane. The combined organic layers were washed with aqueous saturated sodium bicarbonate solution (30 ml), dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by chromatography to obtain N-[5-ethylsulfonyl-6-[3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridin-2-yl]-3-pyridyl]-N-methyl-2-methylsulfonyl-acetamide.

[0469] LCMS (method 2): Rt 0.83 min, 520 (M+H).

[0470] 1H NMR (400 MHz, CDCl.sub.3) ppm 1.41 (t, 3H) 1.92-2.10 (m, 1H) 3.23 (s, 3H) 3.51 (br s, 2H) 3.60-3.83 (m, 1H) 3.83-4.00 (m, 6H) 4.10-4.52 (m, 1H) 4.36 (br s, 1H) 8.03-8.26 (m, 1H) 8.32-8.79 (m, 1H) 8.86-9.13 (m, 2H).

Example H3: Preparation of N-[5-ethylsulfanyl-6-[3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridin-2-yl]-3-pyridyl]-N-methyl-acetamide (compound P33, Table P)

[0471] ##STR00087##

Step A: Preparation of 5-ethylsulfanyl-N-methyl-6-[3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridin-2-yl]pyridin-3-amine

[0472] ##STR00088##

[0473] In a dried vessel, 2-(5-bromo-3-ethylsulfanyl-2-pyridyl)-3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridine (1.0 g, 2.4 mmol, prepared as described in WO 2016/005263) was dissolved in tetrahydrofuran (3 mL). Copper (0.03 g, 0.48 mmol), copper sulfate (0.077 g., 0.48 mmol) and methanamine (2.2 mL, 24 mmol) 40% MeNH.sub.2 in H.sub.2O were added. The vessel was closed and stirred at 100 C. until completion. After cooling at room temperature, pressure was released and reaction mixture was diluted with water. The aqueous layer was extracted with ethyl acetate. The combined organic layers were washed with water, brine solution, dried with anhydrous sodium sulfate and concentrated under reduced pressure. The crude was purified by chromatography to afford 5-ethylsulfanyl-N-methyl-6-[3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridin-2-yl]pyridin-3-amine.

[0474] LCMS (method 2): Rt 0.91 min, 368 (M+H).

[0475] .sup.1H NMR (400 MHz, CDCl.sub.3) ppm 1.34 (t, J=7.34 Hz, 3H) 2.90-3.01 (m, 5H) 4.05 (s, 3H) 6.93 (br s, 1H) 8.04 (br d, J=8.56 Hz, 1H) 8.21 (br d, J=1.47 Hz, 1H) 8.94 (br s, 1H).

Step B: Preparation of N-[5-ethylsulfanyl-6-[3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridin-2-yl]-3-pyridyl]-N-methyl-acetamide (compound P33, Table P)

[0476] ##STR00089##

[0477] To a suspension of 5-ethylsulfanyl-N-methyl-6-[3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridin-2-yl]pyridin-3-amine (0.400 g, 1.09 mmol) in pyridine (5 mL) was added N,N-dimethylpyridin-4-amine (0.0269 g, 0.218 mmol) followed by acetyl chloride (0.171 g, 2.18 mmol) at room temperature. Resulting reaction was stirred at room temperature for 16 h. Pyridine was concentrated under vacuum. Water (20 mL) was added to the reaction mass and extracted with ethyl acetate (10 mL2). Combined organic layers were washed with brine (20 mL), dried on sodium sulfate and concentrated under reduced pressure to afford the crude compound. Purification using Combi-Flash Silica-Gel (2% methanol in DCM) afforded the title compound.

[0478] LCMS (method 2): Rt 0.87 min, 410 (M+H).

[0479] 1H NMR (400 MHz, DMSO-d6) ppm 1.21 (t, 3H) 2.04 (br s, 3H) 3.06 (q, 2H) 4.02 (s, 3H) 8.04 (m, 1H) 8.28 (m, 1H) 8.59 (d, 1H) 9.25 (s, 1H).

[0480] Alternative synthesis of 5-ethylsulfanyl-N-methyl-6-[3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridin-2-yl]pyridin-3-amine

##STR00090##

Step A: Preparation of tert-butyl N-[5-ethylsulfanyl-6-[3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridin-2-yl]-3-pyridyl]carbamate

[0481] ##STR00091##

[0482] To a solution of 2-(5-bromo-3-ethylsulfanyl-2-pyridyl)-3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridine (10 g, 23.97 mmol, prepared as described in WO 2016/005263) in 1,4-dioxane (100 mL) were added tert-butyl carbamate (3.37 g, 28.76 mmol), cesium carbonate (10.94 g, 33.56 mmol) and XPhos (2.09 g, 4.314 mmol, 98 mass %). The resulting mixture was degassed for 30 min with argon and then palladium(II) acetate (0.326 g, 1.438 mmol) was added. The resulting mixture was degassed again 10 min with argon and then stirred at 110 C. for 14-15 hours. The reaction mixture was cooled down to room temperature and quenched with water (200 mL). The aqueous layer was extracted with ethyl acetate (100 mL3), and the combined organic layers were then washed with brine (100 mL), dried over sodium sulfate and concentrated in vacuo to afford crude compound. The crude was purified by chromatography over silica gel to afford the pure tert-butyl N-[5-ethylsulfanyl-6-[3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridin-2-yl]-3-pyridyl]carbamate as a white solid.

[0483] LCMS (method 2): Rt 1.11 min, 455 (M+H).

[0484] .sup.1H NMR (400 MHz, CDCl.sub.3) ppm 1.18-1.29 (m, 2H) 1.36 (t, J=7.40 Hz, 1H) 1.34-1.39 (m, 1H) 1.34-1.39 (m, 1H) 1.55 (s, 9H) 1.72 (s, 3H) 2.05 (s, 1H) 2.94-3.03 (m, 2H) 4.03 (s, 3H) 6.93-7.08 (m, 1H) 8.10-8.21 (m, 1H) 8.16-8.22 (m, 1H) 8.31 (d, J=2.20 Hz, 1H) 8.93 (s, 1H).

Step B: Preparation of tert-butyl N-[5-ethylsulfanyl-6-[3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridin-2-yl]-3-pyridyl]-N-methyl-carbamate

[0485] ##STR00092##

[0486] To a solution of tert-butyl N-[5-ethylsulfanyl-6-[3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridin-2-yl]-3-pyridyl]carbamate (2 g, 4.41 mmol) in N,N-dimethylformamide (20 mL) was added cesium carbonate (1.72 g, 5.292 mmol, 99.995 mass %) and iodomethane (0.333 mL, 5.292 mmol), and the reaction mixture was then stirred at room temperature until completion. The reaction mixture was then diluted with water (200 ml) and the aqueous layer was extracted with ethyl acetate (3100 ml). The combined organic layer was dried over sodium sulfate, filtered and concentrated in vacuo to afford tert-butyl N-[5-ethylsulfanyl-6-[3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridin-2-yl]-3-pyridyl]-N-methyl-carbamate as a white solid.

[0487] LCMS (method 2): Rt 1.11 min, 468 (M+H).

[0488] .sup.1H NMR (DMSO-d6) : 9.23 (s, 1H), 8.57 (d, J=2.2 Hz, 1H), 8.27 (s, 1H), 7.95 (d, J=2.2 Hz, 1H), 4.00 (s, 3H), 3.33 (s, 3H), 3.02 (q, J=7.3 Hz, 2H), 1.46 (s, 9H), 1.21 (t, J=7.3 Hz, 3H).

Step C: Preparation of 5-ethylsulfanyl-N-methyl-6-[3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridin-2-yl]pyridin-3-amine

[0489] ##STR00093##

[0490] To a solution of tert-butyl N-[5-ethylsulfanyl-6-[3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridin-2-yl]-3-pyridyl]-N-methyl-carbamate (2.2 g, 4.7 mmol) in dichloromethane (15 mL) was added 2,2,2-trifluoroacetic acid (0.8 g, 7.1 mmol). The resulting mixture was stirred overnight at room temperature. The reaction mixture was quenched with bicarbonate solution and the aqueous layer was extracted with dichloromethane. The combined organic layers were washed with water, brine solution, dried with anhydrous sodium sulfate and concentrated under reduced pressure to afford 5-ethylsulfanyl-N-methyl-6-[3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridin-2-yl]pyridin-3-amine.

[0491] LCMS (method 2): Rt 0.91 min, 368 (M+H).

[0492] .sup.1H NMR (400 MHz, CDCl.sub.3) ppm 1.34 (t, J=7.34 Hz, 3H) 2.90-3.01 (m, 5H) 4.05 (s, 3H) 6.93 (br s, 1H) 8.04 (br d, J=8.56 Hz, 1H) 8.21 (br d, J=1.47 Hz, 1H) 8.94 (br s, 1H).

Example H4: Preparation of N-[5-ethylsulfonyl-6-[3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridin-2-yl]-3-pyridyl]-2,2-difluoro-N-methyl-acetamide (compound P13, Table P)

[0493] ##STR00094##

[0494] 5-ethylsulfonyl-N-methyl-6-[3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridin-2-yl]pyridin-3-amine (0.8 mmol, 0.3 g, prepared a described in example P1 step D) and 2,2-difluoroacetic acid (0.9 mmol, 0.09 g) was dissolved in pyridine at room temperature under nitrogen. The reaction mixture was cooled (around 0-10 C.) and phosphorus oxychloride (0.9 mmol, 0.1 g) was added dropwise under nitrogen. The reaction mixture was stirred at around 10 C. to 0 C. for 30 minutes until completion. The reaction mixture was slowly quenched in cold water and diluted with ethyl acetate. The organic layer was separated and the aqueous layer was further washed with ethyl acetate. The combined organic layers were washed with brine, dried over sodium sulphate and concentrated in vacuo. The residue was purified by chromatography over silica gel to obtain N-[5-ethylsulfonyl-6-[3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridin-2-yl]-3-pyridyl]-2,2-difluoro-N-methyl-acetamide. LCMS (method 2): Rt 1.30 min, 478 [M+H].

[0495] 1H NMR (400 MHz, CDCl.sub.3) ppm 1.34-1.44 (m, 3H) 3.94 (s, 5H) 3.71-4.04 (m, 1H) 5.52-6.93 (m, 1H) 8.03-8.22 (m, 1H) 8.12 (s, 1H) 8.48 (d, 1H) 8.83-9.11 (m, 1H) 8.98 (br d, 1H).

Example H5: Preparation of N-[5-ethylsulfonyl-6-[3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridin-2-yl]-3-pyridyl]-2-methoxy-N-methyl-acetamide (compound P12, Table P)

[0496] ##STR00095##

[0497] 5-ethylsulfonyl-N-methyl-6-[3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridin-2-yl]pyridin-3-amine (0.5 mmol, 0.2 g) was dissolved in pyridine (3 ml) and 2-methoxyacetyl chloride (0.55 mmol, 0.052 mL) was added dropwise. Reaction mixture was stirred for 3 hours at room temperature and poured into water (30 ml), the aqueous layer was extracted with diethyl ethyl acetate. The combined organic layers were washed with aqueous saturated sodium chloride solution (30 ml), dried over anhydrous sodium sulfate, and concentrated of under reduced pressure. The residue was purified by chromatography to afford N-[5-ethylsulfonyl-6-[3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridin-2-yl]-3-pyridyl]-2-methoxy-N-methyl-acetamide not pure.

[0498] LCMS (method 2): Rt 0.85 min, 472 [M+H].

[0499] 1H NMR (400 MHz, CDCl.sub.3) ppm 1.39 (t, 3H) 1.66 (br s, 1H) 3.41-3.55 (m, 6H) 3.84 (q, 2H) 3.93 (s, 3H) 4.21 (br s, 2H) 8.12 (d, 1H) 8.44 (d, 1H) 9.00 (s, 2H).

Example H6: Preparation of N-[5-ethylsulfonyl-6-[3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridin-2-yl]-3-pyridyl]-N-methyl-cyclopropanecarboxamide (compound P9, Table P)

[0500] ##STR00096##

[0501] 5-Ethylsulfonyl-N-methyl-6-[3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridin-2-yl]pyridin-3-amine (0.50 g, 1.3 mmol, preparation described in example H1, step D) was dissolved in tetrahydrofuran (15 mL). N,N-diethylethanamine (3 equiv., 3.8 mmol, 99 mass %) was added dropwise, followed by the addition of cyclopropanecarbonyl chloride (1.6 mmol, 0.17 g) dropwise at room temperature. The resulting reaction mixture was stirred at room temperature for 3 hours. After completion of reaction, reaction mixture was then poured into water (20 ml) and extracted with ethyl acetate (320 ml). The combined extracts were washed with brine, dried with sodium sulfate and evaporated under reduced pressure to give the crude product. This crude was purified by chromatography to afford N-[5-ethylsulfonyl-6-[3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridin-2-yl]-3-pyridyl]-N-methyl-cyclopropanecarboxamide LCMS (method 2): Rt 0.86 min, 468 [M+H].

[0502] 1H NMR (400 MHz, CDCl.sub.3) ppm 0.90-0.96 (m, 2H) 1.19-1.23 (m, 2H) 1.24-1.31 (m, 1H) 1.35-1.43 (m, 3H) 3.53-3.59 (m, 3H) 3.79-3.87 (m, 2H) 3.94 (s, 3H) 8.12 (s, 1H) 8.43-8.49 (m, 1H) 8.98-9.03 (m, 2H).

Example H7: Preparation of N-[5-ethylsulfonyl-6-[3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridin-2-yl]-3-pyridyl]-N-methoxy-cyclopropanecarboxamide (compound P24, Table P)

[0503] ##STR00097##

[0504] To a solution of 2-(5-bromo-3-ethylsulfonyl-2-pyridyl)-3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridine (250 mg, 0.557 mmol, prepared as described in WO 2016/005263) in toluene (2.8 mL) was treated with cesium carbonate (363 mg, 1.11 mmol) and N-methoxycyclopropanecarboxamide (70 mg, 0.612 mmol). The reaction mixture was degassed for 10 min with nitrogen and then tert-BuBrettPhos-Pd-G3, [(2-di-tert-butylphosphino-3,6-dimethoxy-2,4,6-triisopropyl-1,1-biphenyl)-2-(2-amino-1,1-biphenyl)]palladium(II) methanesulfonate (22 mg., 0.0278 mmol) was added. The reaction mixture was degassed a second time 10 min and then stirred at 90 C. for one night. At room temperature the reaction mixture was quenched with water (20 mL) and ethyl acetate (10 mL). The resulting mixture was filtered through celite bed, washed with ethyl acetate (210 ml). The two layers were separated and the organic layer was washed with brine (10 ml), dried on sodium sulfate and concentrated in vacuo to afford crude product. This was purified by chromatography over silica gel afford N-[5-ethylsulfonyl-6-[3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridin-2-yl]-3-pyridyl]-N-methoxy-cyclopropanecarboxamide.

[0505] LCMS (method 2): Rt 1.0 min, 484 (M+H).

[0506] 1H NMR (400 MHz, CDCl.sub.3) ppm 1.07-1.14 (m, 2H) 1.21-1.28 (m, 2H) 1.37-1.42 (m, 3H) 2.42-2.48 (m, 1H) 3.77-3.87 (m, 2H) 3.92 (s, 3H) 4.01 (s, 3H) 8.11 (s, 1H) 8.71 (d, J=2.32 Hz, 1H) 8.98 (s, 1H) 9.35 (d, J=2.32 Hz, 1H).

Example H8: Preparation of N-[5-ethylsulfanyl-6-[3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridin-2-yl]-3-pyridyl]-2-hydroxy-2-methyl-propanamide (compound P7, Table P)

[0507] ##STR00098##

[0508] 5-Ethylsulfanyl-6-[3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridin-2-yl]pyridin-3-ol (preparation described in WO 2016/005263) (0.5 g, 1.411 mmol) was dissolved in acetonitrile (14 mL). Then cesium carbonate (1.149 g, 3.527 mmol) was added, the resulting suspension was stirred 5 min and 2-bromo-2-methyl-propanamide (commercially available CAS 7462-74-0) (0.2576 g, 1.552 mmol) was added. Reaction mixture obtained was stirred one night at 70 C. and cooled down at room temperature. Solvent was evaporated and the residue was dissolved in water and ethylacetate. The aqueous layer was acidified and then was extracted with ethylacetate. The combined organic layer was dried over sodium sulfate, filtered and concentrated in vacuo. The crude product was purified by chromatography over silica gel to afford N-[5-ethylsulfanyl-6-[3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridin-2-yl]-3-pyridyl]-2-hydroxy-2-methyl-propanamide.

[0509] LCMS (method 1): Rt 0.9 min, 440 (M+H).

[0510] 1H NMR (400 MHz, DMSO-d6) ppm 1.26 (t, J=7.34 Hz, 3H) 1.41 (s, 6H) 2.97 (q, J=7.34 Hz, 2H) 4.00 (s, 3H) 5.89-5.94 (m, 1H) 8.26 (d, J=0.73 Hz, 1H) 8.49 (d, J=1.83 Hz, 1H) 9.06 (d, J=2.20 Hz, 1H) 9.22 (s, 1H) 10.26-10.31 (m, 1H).

Example H9: Preparation of N-[5-ethylsulfonyl-6-[3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridin-2-yl]-3-pyridyl]-2-hydroxy-2-methyl-propanamide (compound P8, Table P)

[0511] ##STR00099##

[0512] N-[5-ethylsulfanyl-6-[3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridin-2-yl]-3-pyridyl]-2-hydroxy-2-methyl-propanamide (0.14 g, 0.3186 mmol) was dissolved in dichloromethane (2.8 mL) and the solution obtained was cooled down at 0 C. Then 3-chlorobenzenecarboperoxoic acid (0.1571 g, 0.6372 mmol) was added (suspension) and reaction was stirred 30 at 0 C. then warmed up at room temperature and stirred 3 hours. The suspension was become a solution. Reaction mixture was quenched with NaOH 1 M (5 mL) and sodium thiosulfate sol (5 mL). The aqueous layer was extracted 3 times with dichloromethane. The combined organic layer was washed with NaOH 1M 2 times, brine, dried over Na.sub.2SO.sub.4, filtered and concentrated in vacuo to give N-[5-ethylsulfonyl-6-[3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridin-2-yl]-3-pyridyl]-2-hydroxy-2-methyl-propanamide.

[0513] LCMS (method 1): Rt 0.83 min, 472 (M+H).

[0514] 1H NMR (400 MHz, DMSO-d6) ppm 1.21 (t, J=7.52 Hz, 3H) 1.43 (s, 6H) 3.78 (q, J=7.34 Hz, 2H) 3.86 (s, 3H) 5.92 (s, 1H) 8.28 (d, J=0.73 Hz, 1H) 9.10 (d, J=2.57 Hz, 1H) 9.27 (s, 1H) 9.44 (d, J=2.20 Hz, 1H) 10.65-10.69 (m, 1H).

Example H10: Preparation of N-[5-ethylsulfanyl-6-[3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridin-2-yl]-3-pyridyl]cyclopropanecarboxamide (compound P1, Table P)

[0515] ##STR00100##

[0516] To a solution of 2-(5-bromo-3-ethylsulfanyl-2-pyridyl)-3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridine (0.5 g, 1.198 mmol, prepared as described in WO 2016/005263), cyclopropanecarboxamide (104.1 mg, 1.198 mmol), cesium carbonate (1.367 g, 4.195 mmol) and (5-diphenylphosphanyl-9,9-dimethyl-xanthen-4-yl)-diphenyl-phosphane (0.03575 g, 0.05992 mmol; xantphos) in 1,4-dioxane (9.6 mL) under argon was added (1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladium (0.01131 g, 0.01198 mmol; Pd(dba).sub.2) at room temperature. The mixture was heated at 95 C. for a total of two days, with further additions of Xantphos (twice 0.05 equiv.) and bis(dibenzylideneacetone)palladium(0) (twice 0.1 equiv.). After dilution with water, the product was extracted with ethyl acetate, the combined organic layers were dried using anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified using combiflash silica gel to afford N-[5-ethylsulfanyl-6-[3-methyl-6-(trifluoromethyl) imidazo[4,5-c]pyridin-2-yl]-3-pyridyl]cyclopropane-carboxamide as a solid.

[0517] 1H NMR (400 MHz, CDCl.sub.3) ppm 0.96 (dq, J=7.61, 3.82 Hz, 2H) 1.13-1.20 (m, 2H) 1.35 (t, J=7.34 Hz, 3H) 1.60-1.66 (m, 1H) 2.97 (q, J=7.58 Hz, 2H) 4.03 (s, 3H) 7.94 (s, 1H) 8.18 (s, 1H) 8.34 (d, J=2.20 Hz, 1H) 8.45 (d, J=2.20 Hz, 1H) 8.94 (s, 1H).

Example H11: Preparation of 1-[5-ethylsulfonyl-6-[3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridin-2-yl]-3-pyridyl]pyrrolidin-2-one (compound P5, Table P)

[0518] ##STR00101##

[0519] To a solution of 2-(5-bromo-3-ethylsulfonyl-2-pyridyl)-3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridine (100 mg, 0.223 mmol, prepared as described in WO 2016/005263) in 1,4-dioxane (5 mL) in a microwave vial were added pyrrolidin-2-one (1.2 equiv., 0.267 mmol), cesium carbonate (1.4 equiv., 0.312 mmol) and XPhos (0.18 equiv., 0.040 mmol). The mixture was flushed with argon for 30 minutes, then palladium(II) acetate (0.06 equiv., 0.013 mmol) was added, the vial was capped and the reaction mixture heated at 110 C. for 20 minutes in the microwave, and further at reflux with conventional heating for 14 hours. After dilution with water, the mixture was filtered through a sintered funnel and the solid residue washed with ethyl acetate and water. The layers of the filtrate were separated, the organic layer was washed with brine, dried on sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified using combiflash silica gel (2% methanol in dichloromethane) to afford 1-[5-ethylsulfonyl-6-[3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridin-2-yl]-3-pyridyl]pyrrolidin-2-one as a solid.

[0520] LCMS (method 2): Rt 0.90 min, 454 (M+H).

[0521] 1H NMR (400 MHz, DMSO-d6) ppm 1.17 (t, J=7.40 Hz, 3H) 2.15 (quin, J=7.52 Hz, 2H) 2.30 (s, 1H) 2.60 (t, J=8.07 Hz, 2H) 3.74-3.82 (m, 2H) 3.82-3.85 (m, 3H) 4.02 (t, J=7.03 Hz, 2H) 8.26-8.28 (m, 1H) 8.28-8.30 (m, 1H) 9.01 (d, J=2.45 Hz, 1H) 9.19 (d, J=2.45 Hz, 1H) 9.25 (s, 1H).

Example H12: Preparation of 4-[5-ethylsulfonyl-6-[3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridin-2-yl]-3-pyridyl]morpholin-3-one (compound P15, Table P)

[0522] ##STR00102##

[0523] To a solution of 2-(5-bromo-3-ethylsulfonyl-2-pyridyl)-3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridine (400 mg, 0.891 mmol, prepared as described in WO 2016/005263) in 1,4-dioxane (2 mL) in a microwave vial were added morpholin-3-one (1.2 equiv., 1.069 mmol), cesium carbonate (1.4 equiv., 1.247 mmol) and Xantphos (0.14 equiv., 0.125 mmol). The mixture was flushed with nitrogen for 15 minutes, tris(dibenzylideneacetone)dipalladium(0) Pd.sub.2(dba).sub.3 (0.03 equiv., 0.0267 mmol) was added, the vial was capped and heated in the microwave at 110 C. for 120 minutes. After dilution with water, the product was extracted with ethyl acetate, the combined organic layers were filtered over a celite bed, dried using anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified using combiflash silica gel (70% ethyl acetate in cyclohexane) to afford 4-[5-ethylsulfonyl-6-[3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridin-2-yl]-3-pyridyl]morpholin-3-one as a solid.

[0524] LCMS (method 2): Rt 0.85 min, 470 (M+H).

[0525] 1H NMR (400 MHz, DMSO-d6) ppm 1.22 (t, J=7.40 Hz, 3H) 3.80 (q, J=7.30 Hz, 2H) 3.89 (s, 3H) 4.03-4.09 (m, 4H) 4.35 (s, 2H) 8.30 (s, 1H) 8.71 (d, J=2.20 Hz, 1H) 9.25 (d, J=2.20 Hz, 1H) 9.29 (s, 1H).

Example H13: Preparation of N-[5-ethylsulfonyl-6-[3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridin-2-yl]-3-pyridyl]-2,2-dimethyl-propanamide (compound P39, Table P)

[0526] ##STR00103##

Step A: Preparation of 5-ethylsulfonyl-6-[3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridin-2-yl]pyridin-3-amine

[0527] ##STR00104##

[0528] To a solution of tert-butyl N-[5-ethylsulfonyl-6-[3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridin-2-yl]-3-pyridyl]carbamate (10 g, 20.60 mmol; described above in Example H1, step A) in dichloromethane (100 mL) was added 2,2,2-trifluoroacetic acid (20 mL, 259.6 mmol) and the reaction mixture stirred at room temperature overnight. The mixture was quenched with an aqueous sodium bicarbonate solution, the product extracted with ethyl acetate (350 ml), the combined organic layers dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by combiflash (silica gel, 50% ethyl acetate-cyclohexane) to afford 5-ethylsulfonyl-6-[3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridin-2-yl]pyridin-3-amine.

[0529] LCMS (method 1): Rt 1.25 min, 386 (M+H).

[0530] 1H NMR (400 MHz, CDCl.sub.3) =9.20 (s, 1H), 8.31 (d, 1H), 8.21 (s, 1H), 7.59 (d, 1H), 6.35-5.86 (m, 2H), 3.81 (s, 3H), 3.79-3.71 (m, 2H), 1.18 (t, 3H).

Step B: Preparation of N-[5-ethylsulfonyl-6-[3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridin-2-yl]-3-pyridyl]-2,2-dimethyl-propanamide (compound P39, Table P)

[0531] ##STR00105##

[0532] To a solution of 5-ethylsulfonyl-6-[3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridin-2-yl]pyridin-3-amine (400 mg, 1.038 mmol) in a mixture of dichloromethane (6 mL) and tetrahydrofuran (6 mL) under nitrogen at 0 C. was added triethylamine (1.5 equiv., 1.557 mmol), followed by 2,2-dimethylpropanoyl chloride (1.2 equiv., 1.245 mmol) dropwise and the reaction mixture was stirred overnight at room temperature. Dichloromethane and water were added, the layers separated, the organic phase dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was purified by combiflash (40% ethyl acetate in cyclohexane) to afford N-[5-ethylsulfonyl-6-[3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridin-2-yl]-3-pyridyl]-2,2-dimethyl-propanamide as a solid.

[0533] LCMS (method 2): Rt 1.00 min, 470 (M+H).

[0534] 1H NMR (400 MHz, CDCl.sub.3) ppm 1.28-1.31 (m, 12H) 3.71-3.78 (m, 2H) 3.81 (s, 3H) 7.75 (s, 1H) 8.03 (s, 1H) 8.57 (d, J=2.20 Hz, 1H) 8.89 (s, 1H) 9.30 (d, J=2.32 Hz, 1H).

Example H14: Preparation of N-[5-ethylsulfonyl-6-[3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridin-2-yl]-3-pyridyl]-N,2,2-trimethyl-propanamide (compound P26, Table P)

[0535] ##STR00106##

[0536] To a solution of N-[5-ethylsulfonyl-6-[3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridin-2-yl]-3-pyridyl]-2,2-dimethyl-propanamide (0.3 g, 0.639 mmol; compound P39 described above) in N,N-dimethylformamide (2 mL) were added cesium carbonate (1.3 equiv., 0.831 mmol), followed by iodomethane (1.3 equiv., 0.831 mmol) and the reaction mixture was stirred overnight at room temperature. Water was added and the product extracted with ethyl acetate. The combined organic layers were washed with water and brine, dried over anhydrous sodium sulfate and concentrate under reduced pressure. The residue was purified by combiflash (40% ethyl acetate in cyclohexane) to afford N-[5-ethylsulfonyl-6-[3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridin-2-yl]-3-pyridyl]-N,2,2-trimethyl-propanamide as a solid.

[0537] LCMS (method 2): Rt 0.99 min, 484 (M+H).

[0538] 1H NMR (400 MHz, CDCl.sub.3) ppm 1.25 (s, 9H) 1.31 (t, J=7.34 Hz, 3H) 3.47 (s, 3H) 3.77 (q, J=7.17 Hz, 2H) 3.85 (s, 3H) 8.04 (s, 1H) 8.32 (s, 1H) 8.82 (s, 1H) 8.92 (s, 1H).

TABLE-US-00013 TABLE P Examples of compounds of formula (I) RT Entry IUPAC name STRUCTURE (min) [M + H] Method MP C. P1 N-[5-ethylsulfanyl-6- [3-methyl-6- (trifluoromethyl)imida- zo[4,5-c]pyridin-2-yl]- 3- pyridyl]cyclopropane carboxamide [00107] 0.93 422 1 P2 N-[5-ethylsulfonyl-6- [3-methyl-6- (trifluoromethyl)imida- zo[4,5-c]pyridin-2-yl]- 3- pyridyl]cyclopropane carboxamide [00108] 0.89 454 1 311.7- 316.6 P3 N-[3-ethylsulfonyl-4- [3-methyl-6- (trifluoromethyl)imida- zo[4,5-c]pyridin-2- yl]phenyl]-2,2,2- trifluoro-acetamide [00109] 260- 260 P4 N-[5-ethylsulfonyl-6- [3-methyl-6- (trifluoromethyl)imida- zo[4,5-c]pyridin-2-yl]- 3-pyridyl]acetamide [00110] 1.30 428 1 124- 126 P5 1-[5-ethylsulfonyl-6- [3-methyl-6- (trifluoromethyl)imida- zo[4,5-c]pyridin-2-yl]- 3-pyridyl]pyrrolidin-2- one [00111] 0.90 454 2 297- 299 P6 N-[5-ethylsulfonyl-6- [3-methyl-6- (trifluoromethyl)imida- zo[4,5-c]pyridin-2-yl]- 3-pyridyl]-N-methyl- acetamide [00112] 1.25 442 1 213- 215 P7 N-[5-ethylsulfanyl-6- [3-methyl-6- (trifluoromethyl)imida- zo[4,5-c]pyridin-2-yl]- 3-pyridyl]-2-hydroxy- 2-methyl- propanamide [00113] 0.87 440 1 195- 196 P8 N-[5-ethylsulfonyl-6- [3-methyl-6- (trifluoromethyl)imida- zo[4,5-c]pyridin-2-yl]- 3-pyridyl]-2-hydroxy- 2-methyl- propanamide [00114] 0.85 472 1 222- 225 P9 N-[5-ethylsulfonyl-6- [3-methyl-6- (trifluoromethyl)imida- zo[4,5-c]pyridin-2-yl]- 3-pyridyl]-N-methyl- cyclopropanecarboxa- mide [00115] 0.96 468 2 172- 174 P10 N-cyclopropyl-N-[5- ethylsulfonyl-6-[3- methyl-6- (trifluoromethyl)imida- zo[4,5-c]pyridin-2-yl]- 3-pyridyl]acetamide [00116] 1.36 468 1 111- 113 P11 N-[5-ethylsulfonyl-6- [3-methyl-6- (trifluoromethyl)imida- zo[4,5-c]pyridin-2-yl]- 3-pyridyl]-2,2,2- trifluoro-N-methyl- acetamide [00117] 1.41 496 1 186- 188 P12 N-[5-ethylsulfonyl-6- [3-methyl-6- (trifluoromethyl)imida- zo[4,5-c]pyridin-2-yl]- 3-pyridyl]-2-methoxy- N-methyl-acetamide [00118] 0.83 472 2 148- 150 P13 N-[5-ethylsulfonyl-6- [3-methyl-6- (trifluoromethyl)imida- zo[4,5-c]pyridin-2-yl]- 3-pyridyl]-2,2- difluoro-N-methyl- acetamide [00119] 1.32 478 1 200- 202 P14 N-[5-ethylsulfonyl-6- [3-methyl-6- (trifluoromethyl)imida- zo[4,5-c]pyridin-2-yl]- 3-pyridyl]-N-methyl- 2-methylsulfanyl- acetamide [00120] 0.91 488 2 178- 180 P15 4-[5-ethylsulfonyl-6- [3-methyl-6- (trifluoromethyl)imida- zo[4,5-c]pyridin-2-yl]- 3-pyridyl]morpholin- 3-one [00121] 0.85 470 2 244- 246 P16 N-[3-ethylsulfonyl-4- [3-methyl-6- (trifluoromethyl)imida- zo[4,5-c]pyridin-2- yl]phenyl]-N-methyl- acetamide [00122] 1.153 442 1 223- 225 P17 N-[5-ethylsulfonyl-6- [3-methyl-6- (trifluoromethyl)imida- zo[4,5-c]pyridin-2-yl]- 3-pyridyl]-N-methyl- 2-methylsulfonyl- acetamide [00123] 0.83 520 2 248- 250 P18 4-[5-ethylsulfonyl-6- [3-methyl-6- (trifluoromethyl)imida- zo[4,5-c]pyridin-2-yl]- 3-pyridyl]-1,1-dioxo- 1,4-thiazinan-3-one [00124] 0.84 518 2 180- 182 P19 4-[5-ethyslulfonyl-6- [3-methyl-6- (trifluoromethyl)imida- zo[4,5-c]pyridin-2-yl]- 3- pyridyl]thiomorpholin- 3-one [00125] 0.90 486 2 211- 213 P20 2-chloro-N-ethyl-N- [5-ethylsulfonyl-6-[3- methyl-6- (trifluoromethyl)imida- zo[4,5-c]pyridin-2-yl]- 3-pyridyl]acetamide [00126] 0.94 490/ 492 2 169- 171 P21 N-ethyl-N-[5- ethylsulfonyl-6-[3- methyl-6- (trifluoromethyl)imida- zo[4,5-c]pyridin-2-yl]- 3-pyridyl]acetamide [00127] 0.86 456 2 163- 165 P22 2-chloro-N-[5- ethylsulfonyl-6-[3- methyl-6- (trifluoromethyl)imida- zo[4,5-c]pyridin-2-yl]- 3-pyridyl]-N-methyl- acetamide [00128] 0.92 476/ 478 2 192- 194 P23 N-[5-ethylsulfonyl-6- [3-methyl-6- (trifluoromethyl)imida- zo[4,5-c]pyridin-2-yl]- 3-pyridyl]-N-methyl- propanamide [00129] 0.91 456 2 149- 151 P24 N-[5-ethylsulfonyl-6- [3-methyl-6- (trifluoromethyl)imida- zo[4,5-c]pyridin-2-yl]- 3-pyridyl]-N- methoxy- cyclopropanecarboxa- mide [00130] 1.02 484 2 182- 184 P25 N-[5-ethylsulfonyl-6- [3-methyl-6- (trifluoromethyl)imida- zo[4,5-c]pyridin-2-yl]- 3- pyridyl]propanamide [00131] 0.89 442 2 252- 254 P26 N-[5-ethylsulfonyl-6- [3-methyl-6- (trifluoromethyl)imida- zo[4,5-c]pyridin-2-yl]- 3-pyridyl]-N,2,2- trimethyl- propanamide [00132] 0.99 484 2 137- 139 P27 N-[5-ethylsulfonyl-6- [3-methyl-6- (trifluoromethyl)imida- zo[4,5-c]pyridin-2-yl]- 3-pyridyl]-N,2- dimethyl- propanamide [00133] 0.92 470 2 122- 124 P28 N-[5-ethylsulfonyl-6- [3-methyl-6- (trifluoromethyl)imida- zo[4,5-c]pyridin-2-yl]- 3-pyridyl]-3,3,3- trifluoro-N-methyl- propanamide [00134] 0.96 510 2 203- 205 P29 N-[5-ethylsulfonyl-6- [3-methyl-6- (trifluoromethyl)imida- zo[4,5-c]pyridin-2-yl]- 3-pyridyl]-N- methoxy- propanamide [00135] 0.98 472 2 133- 135 P30 N-[5-ethylsulfonyl-6- [3-methyl-6- (trifluoromethyl)imida- zo[4,5-c]pyridin-2-yl]- 3-pyridyl]-N- methoxy-acetamide [00136] 0.94 458 2 187- 189 P31 N-[5-ethylsulfonyl-6- [3-methyl-6- (trifluoromethyl)imida- zo[4,5-c]pyridin-2-yl]- 3-pyridyl]-N-methyl- 3-methylsulfonyl- propanamide [00137] 0.81 534 2 220- 222 P32 N-[5-ethylsulfonyl-6- [3-methyl-6- (trifluoromethyl)imida- zo[4,5-c]pyridin-2-yl]- 3-pyridyl]-N-(2,2,2- trifluoroethyl)propana- mide [00138] 1.447 524 1 106- 108 P33 N-[5-ethylsulfanyl-6- [3-methyl-6- (trifluoromethyl)imida- zo[4,5-c]pyridin-2-yl]- 3-pyridyl]-N-methyl- acetamide [00139] 0.83 472 2 176- 178 P34 3-[5-ethylsulfonyl-6- [3-methyl-6- (trifluoromethyl)imida- zo[4,5-c]pyridin-2-yl]- 3-pyridyl]oxazolidin- 2-one [00140] 0.85 456 2 244- 246 P35 1-[5-ethylsulfonyl-6- [3-methyl-6- (trifluoromethyl)imida- zo[4,5-c]pyridin-2-yl]- 3-pyridyl]-3-methoxy- imidazolidin-2-one [00141] 0.88 485 2 238- 240 P36 1-[5-ethylsulfonyl-6- [3-methyl-6- (trifluoromethyl)imida- zo[4,5-c]pyridin-2-yl]- 3- pyridyl]imidazolidin- 2-one [00142] 0.80 455 2 246- 248 P37 1-[5-ethylsulfonyl-6- [3-methyl-6- (trifluoromethyl)imida- zo[4,5-c]pyridin-2-yl]- 3-pyridyl]-3-methyl- imidazolidin-2-one [00143] 1.32 469 1 255- 257 P38 1-cyano-N-[5- ethylsulfonyl-6-[3- methyl-6- (trifluoromethyl)imida- zo[4,5-c]pyridin-2-yl]- 3-pyridyl]-N-methyl- cyclopropanecarboxa- mide [00144] 0.92 493 2 216- 218 P39 N-[5-ethylsulfonyl-6- [3-methyl-6- (trifluoromethyl)imida- zo[4,5-c]pyridin-2-yl]- 3-pyridyl]-2,2- dimethyl- propanamide [00145] 0.98 470 2 136- 138 P40 N-cyclopropyl-N-[5- ethylsulfonyl-6-[3- methyl-6- (trifluoromethyl)imida- zo[4,5-c]pyridin-2-yl]- 3- pyridyl]propanamide [00146] 0.91 482 2 219- 221 P41 N-[5-ethylsulfonyl-6- [3-methyl-6- (trifluoromethyl)imida- zo[4,5-c]pyridin-2-yl]- 3-pyridyl]-N-methyl- 3-methylsulfanyl- propanamide [00147] 0.91 502 2 189- 191 P42 N-(1- cyanocyclopropyl)-N- [5-ethylsulfonyl-6-[3- methyl-6- (trifluoromethyl)imida- zo[4,5-c]pyridin-2-yl]- 3-pyridyl]acetamide [00148] 0.88 493 2 195- 198 P43 2-cyano-N-[5- ethylsulfonyl-6-[3- methyl-6- (trifluoromethyl)imida- zo[4,5-c]pyridin-2-yl]- 3-pyridyl]-N,2- dimethyl- propanamide [00149] 0.90 495 2 176- 178 P44 N-[5-ethylsulfonyl-6- [3-methyl-6- (trifluoromethyl)imida- zo[4,5-c]pyridin-2-yl]- 3-pyridyl]-2,2,2- trifluoro-acetamide [00150] 0.95 482 2 226- 228 P45 3-[5-ethylsulfonyl-6- [3-methyl-6- (trifluoromethyl)imida- zo[4,5-c]pyridin-2-yl]- 3-pyridyl]thiazolidin- 2-one [00151] 0.96 472 2 231- 233 P46 N-[5-ethylsulfonyl-6- [3-methyl-6- (trifluoromethyl)imida- zo[4,5-c]pyridin-2-yl]- 3-pyridyl]-N- isopropyl-acetamide [00152] 0.98 470 2 108- 110 P47 N-[5-ethylsulfanyl-6- [3-methyl-6- (trifluoromethyl)imida- zo[4,5-c]pyridin-2-yl]- 3-pyridyl]-N- isopropyl-acetamide [00153] 1.01 438 2 148- 150

[0539] 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 of formula I 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. 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.

[0540] The following mixtures of the compounds of formula I with active ingredients are preferred (the abbreviation TX means one compound selected from the group consisting of the compounds described in Tables A-1 to A-17, and B-1 to B-2 and Table P of the present invention): an adjuvant selected from the group of substances consisting of petroleum oils (alternative name) (628)+TX,

[0541] 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 50439 (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, cypermetrin (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, dimpropyridaz+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, fluacry-pyrim (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 1 (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 thuringiensis 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,

[0542] a soil sterilant selected from the group of substances consisting of iodomethane (IUPAC name) (542) and methyl bromide (537)+TX,

[0543] 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,

[0544] 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, sordidin (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,

[0545] 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, El 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, 0,0-diethyl O-4-methyl-2-oxo-2H-chromen-7-yl phosphorothioate (IUPAC name) (1074)+TX, 0,0-diethyl O-6-methyl-2-propylpyrimidin-4-yl phosphorothioate (IUPAC name) (1075)+TX, 0,0,0,0-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 Ill (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, fluxametamide (WO 2007/026965)+TX, epsilon-metofluthrin [240494-71-7]+TX, epsilon-momfluorothrin [1065124-65-3]+TX, fluazaindolizine [1254304-22-7]+TX, chloroprallethrin [399572-87-3]+TX, fluxametamide [928783-29-3]+TX, cyhalodiamide [1262605-53-7]+TX, tioxazafen [330459-31-9]+TX, broflanilide [1207727-04-5]+TX, flufiprole [704886-18-0]+TX, cyclaniliprole [1031756-98-5]+TX, tetraniliprole [1229654-66-3]+TX, guadipyr (described in WO2010/060231)+TX, cycloxaprid (described in WO 2005/077934)+TX, spiropidion+TX, Afidopyropen+TX, flupyrimin+TX, Momfluorothrin+TX, kappa-bifenthrin+TX, kappa-tefluthrin+TX, Dichloromezotiaz+TX, Tetrachloraniliprole+TX, benzpyrimoxan+TX

[0546] 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,

[0547] 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-methylrhodanine (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, fluopyram+TX,

[0548] a nitrification inhibitor selected from the group of substances consisting of potassium ethylxanthate [CCN] and nitrapyrin (580)+TX,

[0549] 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,

[0550] 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,

[0551] 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,

[0552] 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,

[0553] a virucide selected from the group of substances consisting of imanin (alternative name) [CCN] and ribavirin (alternative name) [CCN]+TX,

[0554] a wound protectant selected from the group of substances consisting of mercuric oxide (512)+TX, octhilinone (590) and thiophanate-methyl (802)+TX,

[0555] 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, tebuconazole [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, meta-laxyl [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, acibenzo-lar-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, dimethomorph [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; lancotrione [1486617-21-3]+TX, florpyrauxifen [943832-81-3]+TX, ipfentrifluconazole[1417782-08-1]+TX, mefentrifluconazole [1417782-03-6]+TX, quinofumelin [861647-84-9]+TX, chloroprallethrin [399572-87-3]+TX, cyhalodiamide [1262605-53-7]+TX, fluazaindolizine [1254304-22-7]+TX, fluxametamide [928783-29-3]+TX, epsilon-metofluthrin [240494-71-7]+TX, epsilon-momfluorothrin [1065124-65-3]+TX, pydiflumetofen [1228284-64-7]+TX, kappa-bifenthrin [439680-76-9]+TX, broflanilide [1207727-04-5]+TX, dicloromezotiaz [1263629-39-5]+TX, dipymetitrone [16114-35-5]+TX, pyraziflumid [942515-63-1]+TX, kappa-tefluthrin [391634-71-2]+TX, fenpicoxamid [517875-34-2]+TX; fluindapyr [1383809-87-7]+TX; flufenpyrrolidone+TX, alpha-bromadiolone [28772-56-7]+TX; flupyrimin [1689566-03-7]+TX; benzpyrimoxan [1449021-97-9]+TX; acynonapyr [1332838-17-1]+TX; inpyrfluxam [1352994-67-2]+TX, isoflucypram [1255734-28-1]+TX; isocycloseram+TX, rescalure [64309-03-1]+TX; aminopyrifen [1531626-08-0]+TX; tyclopyrazoflor [1477919-27-9]+TX; and spiropidion [1229023-00-0]+TX; and

[0556] microbials including: Acinetobacter lwoffii+TX, Acremonium alternatum+TX+TX, Acremonium cephalosporium+TX+TX, Acremonium diospyri+TX, Acremonium obclavatum+TX, Adoxophyes orana granulovirus (AdoxGV) (Capex)+TX, Agrobacterium radiobacter strain K84 (Galltrol-A)+TX, Alternaria alternate+TX, Alternaria cassia+TX, Alternaria destruens (Smolder)+TX, Ampelomyces quisqualis (AQ100)+TX, Aspergillus flavus AF36 (AF36)+TX, Aspergillus flavus NRRL 21882 (Aflaguard)+TX, Aspergillus spp. +TX, Aureobasidium pullulans+TX, Azospirillum+TX, (MicroAZ+TX, TAZO B)+TX, Azotobacter+TX, Azotobacter chroocuccum (Azotomeal)+TX, Azotobacter cysts (Bionatural Blooming Blossoms)+TX, Bacillus amyloliquefaciens+TX, Bacillus cereus+TX, Bacillus chitinosporus strain CM-1+TX, Bacillus chitinosporus strain AQ746+TX, Bacillus licheniformis strain HB-2 (Biostart Rhizoboost)+TX, Bacillus licheniformis strain 3086 (EcoGuard+TX, Green Releaf)+TX, Bacillus circulans+TX, Bacillus firmus (BioSafe+TX, BioNem-WP+TX, VOTiVO)+TX, Bacillus firmus strain 1-1582+TX, Bacillus macerans+TX, Bacillus marismortui+TX, Bacillus megaterium+TX, Bacillus mycoides strain AQ726+TX, Bacillus papillae (Milky Spore Powder)+TX, Bacillus pumilus spp. +TX, Bacillus pumilus strain GB34 (Yield Shield)+TX, Bacillus pumilus strain AQ717+TX, Bacillus pumilus strain QST 2808 (Sonata+TX, Ballad Plus)+TX, Bacillus spahericus (VectoLex)+TX, Bacillus spp. +TX, Bacillus spp. strain AQ175+TX, Bacillus spp. strain AQ177+TX, Bacillus spp. strain AQ178+TX, Bacillus subtilis strain QST 713 (CEASE+TX, Serenade+TX, Rhapsody)+TX, Bacillus subtilis strain QST 714 (JAZZ)+TX, Bacillus subtilis strain AQ153+TX, Bacillus subtilis strain AQ743+TX, Bacillus subtilis strain QST3002+TX, Bacillus subtilis strain QST3004+TX, Bacillus subtilis var. amyloliquefaciens strain FZB24 (Taegro+TX, Rhizopro)+TX, Bacillus thuringiensis Cry 2Ae+TX, Bacillus thuringiensis Cry1Ab+TX, Bacillus thuringiensis aizawai GC 91 (Agree)+TX, Bacillus thuringiensis israelensis (BMP123+TX, Aquabac+TX, VectoBac)+TX, Bacillus thuringiensis kurstaki (Javelin+TX, Deliver+TX, CryMax+TX, Bonide+TX, Scutella WP+TX, Turilav WP+TX, Astuto+TX, Dipel WP+TX, Biobit+TX, Foray)+TX, Bacillus thuringiensis kurstaki BMP 123 (Baritone)+TX, Bacillus thuringiensis kurstaki HD-1 (Bioprotec-CAF/3P)+TX, Bacillus thuringiensis strain BD #32+TX, Bacillus thuringiensis strain AQ52+TX, Bacillus thuringiensis var. aizawai (XenTari+TX, DiPel))+TX, bacteria spp. (GROWMEND+TX, GROWSWEET+TX, Shootup)+TX, bacteriophage of Clavipacter michiganensis (AgriPhage)+TX, Bakflor+TX, Beauveria bassiana (Beaugenic+TX, Brocaril WP)+TX, Beauveria bassiana GHA (Mycotrol ES+TX, Mycotrol O+TX, BotaniGuard)+TX, Beauveria brongniartii (Engerlingspilz+TX, Schweizer Beauveria+TX, Melocont)+TX, Beauveria spp. +TX, Botrytis cineria+TX, Bradyrhizobium japonicum (TerraMax)+TX, Brevibacillus brevis+TX, Bacillus thuringiensis tenebrionis (Novodor)+TX, BtBooster+TX, Burkholderia cepacia (Deny+TX, Intercept+TX, Blue Circle)+TX, Burkholderia gladii+TX, Burkholderia gladioli+TX, Burkholderia spp. +TX, Canadian thistle fungus (CBH Canadian Bioherbicide)+TX, Candida butyri+TX, Candida famata+TX, Candida fructus+TX, Candida glabrata+TX, Candida guilliermondii+TX, Candida melibiosica+TX, Candida oleophila strain O+TX, Candida parapsilosis+TX, Candida pelliculosa+TX, Candida pulcherrima+TX, Candida reukaufii+TX, Candida saitoana (Bio-Coat+TX, Biocure)+TX, Candida sake+TX, Candida spp. +TX, Candida tenius+TX, Cedecea dravisae+TX, Cellulomonas flavigena+TX, Chaetomium cochliodes (Nova-Cide)+TX, Chaetomium globosum (Nova-Cide)+TX, Chromobacterium subtsugae strain PRAA4-1T (Grandevo)+TX, Cladosporium cladosporioides+TX, Cladosporium oxysporum+TX, Cladosporium chlorocephalum+TX, Cladosporium spp. +TX, Cladosporium tenuissimum+TX, Clonostachys rosea (EndoFine)+TX, Colletotrichum acutatum+TX, Coniothyrium minitans (Cotans WG)+TX, Coniothyrium spp. +TX, Cryptococcus albidus (YIELDPLUS)+TX, Cryptococcus humicola+TX, Cryptococcus infirmo-miniatus+TX, Cryptococcus laurentii+TX, Cryptophlebia leucotreta granulovirus (Cryptex)+TX, Cupriavidus campinensis+TX, Cydia pomonella granulovirus (CYD-X)+TX, Cydia pomonella granulovirus (Madex+TX, Madex Plus+TX, Madex Max/Carpovirusine)+TX, Cylindrobasidium laeve (Stumpout)+TX, Cylindrocladium+TX, Debaryomyces hansenii+TX, Drechslera hawaiinensis+TX, Enterobacter cloacae+TX, Enterobacteriaceae+TX, Entomophtora virulenta (Vektor)+TX, Epicoccum nigrum+TX, Epicoccum purpurascens+TX, Epicoccum spp. +TX, Filobasidium floriforme+TX, Fusarium acuminatum+TX, Fusarium chlamydosporum+TX, Fusarium oxysporum (Fusaclean/Biofox C)+TX, Fusarium proliferatum+TX, Fusarium spp. +TX, Galactomyces geotrichum+TX, Gliocladium catenulatum (Primastop+TX, Prestop)+TX, Gliocladium roseum+TX, Gliocladium spp. (SoilGard)+TX, Gliocladium virens (Soilgard)+TX, Granulovirus (Granupom)+TX, Halobacillus halophilus+TX, Halobacillus litoralis+TX, Halobacillus trueperi+TX, Halomonas spp. +TX, Halomonas subglaciescola+TX, Halovibrio variabilis+TX, Hanseniaspora uvarum+TX, Helicoverpa armigera nucleopolyhedrovirus (Helicovex)+TX, Helicoverpa zea nuclear polyhedrosis virus (Gemstar)+TX, Isoflavone-formononetin (Myconate)+TX, Kloeckera apiculata+TX, Kloeckera spp. +TX, Lagenidium giganteum (Laginex)+TX, Lecanicillium longisporum (Vertiblast)+TX, Lecanicillium muscarium (Vertikil)+TX, Lymantria Dispar nucleopolyhedrosis virus (Disparvirus)+TX, Marinococcus halophilus+TX, Meira geulakonigii+TX, Metarhizium anisopliae (Met52)+TX, Metarhizium anisopliae (Destruxin WP)+TX, Metschnikowia fruticola (Shemer)+TX, Metschnikowia pulcherrima+TX, Microdochium dimerum (Antibot)+TX, Micromonospora coerulea+TX, Microsphaeropsis ochracea+TX, Muscodor albus 620 (Muscudor)+TX, Muscodor roseus strain A3-5+TX, Mycorrhizae spp. (AMykor+TX, Root Maximizer)+TX, Myrothecium verrucaria strain AARC-0255 (DiTera)+TX, BROS PLUS+TX, Ophiostoma piliferum strain D97 (Sylvanex)+TX, Paecilomyces farinosus+TX, Paecilomyces fumosoroseus (PFR-97+TX, PreFeRal)+TX, Paecilomyces linacinus (Biostat WP)+TX, Paecilomyces lilacinus strain 251 (MeloCon WG)+TX, Paenibacillus polymyxa+TX, Pantoea agglomerans (BlightBan C9-1)+TX, Pantoea spp. +TX, Pasteuria spp. (Econem)+TX, Pasteuria nishizawae+TX, Penicillium aurantiogriseum+TX, Penicillium billai (Jumpstart+TX, TagTeam)+TX, Penicillium brevicompactum+TX, Penicillium frequentans+TX, Penicillium griseofulvum+TX, Penicillium purpurogenum+TX, Penicillium spp. +TX, Penicillium viridicatum+TX, Phlebiopsis gigantean (Rotstop)+TX, phosphate solubilizing bacteria (Phosphomeal)+TX, Phytophthora cryptogea+TX, Phytophthora palmivora (Devine)+TX, Pichia anomala+TX, Pichia guilermondii+TX, Pichia membranaefaciens+TX, Pichia onychis+TX, Pichia stipites+TX, Pseudomonas aeruginosa+TX, Pseudomonas aureofasciens (Spot-Less Biofungicide)+TX, Pseudomonas cepacia+TX, Pseudomonas chlororaphis (AtEze)+TX, Pseudomonas corrugate+TX, Pseudomonas fluorescens strain A506 (BlightBan A506)+TX, Pseudomonas putida+TX, Pseudomonas reactans+TX, Pseudomonas spp. +TX, Pseudomonas syringae (Bio-Save)+TX, Pseudomonas viridiflava+TX, Pseudomons fluorescens (Zequanox)+TX, Pseudozyma flocculosa strain PF-A22 UL (Sporodex L)+TX, Puccinia canaliculata+TX, Puccinia thlaspeos (Wood Warrior)+TX, Pythium paroecandrum+TX, Pythium oligandrum (Polygandron+TX, Polyversum)+TX, Pythium periplocum+TX, Rhanella aquatilis+TX, Rhanella spp. +TX, Rhizobia (Dormal+TX, Vault)+TX, Rhizoctonia+TX, Rhodococcus globerulus strain AQ719+TX, Rhodosporidium diobovatum+TX, Rhodosporidium toruloides+TX, Rhodotorula spp. +TX, Rhodotorula glutinis+TX, Rhodotorula graminis+TX, Rhodotorula mucilagnosa+TX, Rhodotorula rubra+TX, Saccharomyces cerevisiae+TX, Salinococcus roseus+TX, Sclerotinia minor+TX, Sclerotinia minor (SARRITOR)+TX, Scytalidium spp. +TX, Scytalidium uredinicola+TX, Spodoptera exigua nuclear polyhedrosis virus (Spod-X+TX, Spexit)+TX, Serratia marcescens+TX, Serratia plymuthica+TX, Serratia spp. +TX, Sordaria fimicola+TX, Spodoptera littoralis nucleopolyhedrovirus (Littovir)+TX, Sporobolomyces roseus+TX, Stenotrophomonas maltophilia+TX, Streptomyces ahygroscopicus+TX, Streptomyces albaduncus+TX, Streptomyces exfoliates+TX, Streptomyces galbus+TX, Streptomyces griseoplanus+TX, Streptomyces griseoviridis (Mycostop)+TX, Streptomyces lydicus (Actinovate)+TX, Streptomyces lydicus WYEC-108 (ActinoGrow)+TX, Streptomyces violaceus+TX, Tilletiopsis minor+TX, Tilletiopsis spp. +TX, Trichoderma asperellum (T34 Biocontrol)+TX, Trichoderma gamsii (Tenet)+TX, Trichoderma atroviride (Plantmate)+TX, Trichoderma hamatum TH 382+TX, Trichoderma harzianum rifai (Mycostar)+TX, Trichoderma harzianum T-22 (Trianum-P+TX, PlantShield HC+TX, RootShield+TX, Trianum-G)+TX, Trichoderma harzianum T-39 (Trichodex)+TX, Trichoderma inhamatum+TX, Trichoderma koningii+TX, Trichoderma spp. LC 52 (Sentinel)+TX, Trichoderma lignorum+TX, Trichoderma longibrachiatum+TX, Trichoderma polysporum (Binab T)+TX, Trichoderma taxi+TX, Trichoderma virens+TX, Trichoderma virens (formerly Gliocladium virens GL-21) (SoilGuard)+TX, Trichoderma viride+TX, Trichoderma viride strain ICC 080 (Remedier)+TX, Trichosporon pullulans+TX, Trichosporon spp. +TX, Trichothecium spp. +TX, Trichothecium roseum+TX, Typhula phacorrhiza strain 94670+TX, Typhula phacorrhiza strain 94671+TX, Ulocladium atrum+TX, Ulocladium oudemansii (Botry-Zen)+TX, Ustilago maydis+TX, various bacteria and supplementary micronutrients (Natural II)+TX, various fungi (Millennium Microbes)+TX, Verticillium chlamydosporium+TX, Verticillium lecanii (Mycotal+TX, Vertalec)+TX, Vip3Aa20 (VIPtera)+TX, Virgibaclillus marismortui+TX, Xanthomonas campestris pv. Poae (Camperico)+TX, Xenorhabdus bovienii+TX, Xenorhabdus nematophilus; and

[0557] Plant extracts including: pine oil (Retenol)+TX, azadirachtin (Plasma Neem Oil+TX, AzaGuard+TX, MeemAzal+TX, Molt-X+TX, Botanical IGR (Neemazad+TX, Neemix)+TX, canola oil (Lilly Miller Vegol)+TX, Chenopodium ambrosioides near ambrosioides (Requiem)+TX, Chrysanthemum extract (Crisant)+TX, extract of neem oil (Trilogy)+TX, essentials oils of Labiatae (Botania)+TX, extracts of clove rosemary peppermint and thyme oil (Garden insect Killer)+TX, Glycinebetaine (Greenstim)+TX, garlic+TX, lemongrass oil (GreenMatch)+TX, neem oil+TX, Nepeta cataria (Catnip oil)+TX, Nepeta catarina+TX, nicotine+TX, oregano oil (MossBuster)+TX, Pedaliaceae oil (Nematon)+TX, pyrethrum+TX, Quillaja saponaria (NemaQ)+TX, Reynoutria sachalinensis (Regalia+TX, Sakalia)+TX, rotenone (Eco Roten)+TX, Rutaceae plant extract (Soleo)+TX, soybean oil (Ortho Ecosense)+TX, tea tree oil (Timorex Gold)+TX, thymus oil+TX, AGNIQUE MMF+TX, BugOil+TX, mixture of rosemary sesame pepermint thyme and cinnamon extracts (EF 300)+TX, mixture of clove rosemary and peppermint extract (EF 400)+TX, mixture of clove pepermint garlic oil and mint (Soil Shot)+TX, kaolin (Screen)+TX, storage glucam of brown algae (Laminarin); and

[0558] pheromones including: blackheaded fireworm pheromone (3M Sprayable Blackheaded Fireworm Pheromone)+TX, Codling Moth Pheromone (Paramount dispenser-(CM)/Isomate C-Plus)+TX, Grape Berry Moth Pheromone (3M MEC-GBM Sprayable Pheromone)+TX, Leafroller pheromone (3M MEC-LR Sprayable Pheromone)+TX, Muscamone (Snip7 Fly Bait+TX, Starbar Premium Fly Bait)+TX, Oriental Fruit Moth Pheromone (3M oriental fruit moth sprayable Pheromone)+TX, Peachtree Borer Pheromone (Isomate-P)+TX, Tomato Pinworm Pheromone (3M Sprayable Pheromone)+TX, Entostat powder (extract from palm tree) (Exosex CM)+TX, (E+TX,Z+TX,Z)-3+TX,8+TX,11 Tetradecatrienyl acetate+TX, (Z+TX,Z+TX,E)-7+TX,11+TX,13-Hexadecatrienal+TX, (E+TX,Z)-7+TX,9-Dodecadien-1-yl acetate+TX, 2-Methyl-1-butanol+TX, Calcium acetate+TX, Scenturion+TX, Biolure+TX, Check-Mate+TX, Lavandulyl senecioate; and

[0559] Macrobials including: Aphelinus abdominalis+TX, Aphidius ervi (Aphelinus-System)+TX, Acerophagus papaya+TX, Adalia bipunctata (Adalia-System)+TX, Adalia bipunctata (Adaline)+TX, Adalia bipunctata (Aphidalia)+TX, Ageniaspis citrico/a +TX, Ageniaspis fuscicollis+TX, Amblyseius andersoni (Anderline+TX, Andersoni-System)+TX, Amblyseius califomicus (Amblyline+TX, Spical)+TX, Amblyseius cucumeris (Thripex+TX, Bugline Cucumeris)+TX, Amblyseius fallacis (Fallacis)+TX, Amblyseius swirskii (Bugline Swirskii+TX, Swirskii-Mite)+TX, Amblyseius womersleyi (WomerMite)+TX, Amitus hesperidum+TX, Anagrus atomus+TX, Anagyrus fusciventris+TX, Anagyrus kamali+TX, Anagyrus loecki+TX, Anagyrus pseudococci (Citripar)+TX, Anicetus benefices+TX, Anisopteromalus calandrae+TX, Anthocoris nemoralis (Anthocoris-System)+TX, Aphelinus abdominalis (Apheline+TX, Aphiline)+TX, Aphelinus asychis+TX, Aphidius colemani (Aphipar)+TX, Aphidius ervi (Ervipar)+TX, Aphidius gifuensis+TX, Aphidius matricariae (Aphipar-M)+TX, Aphidoletes aphidimyza (Aphidend)+TX, Aphidoletes aphidimyza (Aphidoline)+TX, Aphytis lingnanensis+TX, Aphytis melinus+TX, Aprostocetus hagenowii+TX, Atheta coriaria (Staphyline)+TX, Bombus spp. +TX, Bombus terrestris (Natupol Beehive)+TX, Bombus terrestris (Beeline+TX, Tripol)+TX, Cephalonomia stephanoderis+TX, Chilocorus nigritus+TX, Chrysoperla carnea (Chrysoline)+TX, Chrysoperla carnea (Chrysopa)+TX, Chrysoperla rufilabris+TX, Cirrospilus ingenuus+TX, Cirrospilus quadristriatus+TX, Citrostichus phyllocnistoides+TX, Closterocerus chamaeleon+TX, Closterocerus spp. +TX, Coccidoxenoides perminutus (Planopar)+TX, Coccophagus cowperi+TX, Coccophagus lycimnia+TX, Cotesia flavipes+TX, Cotesia plutellae+TX, Cryptolaemus montrouzieri (Cryptobug+TX, Cryptoline)+TX, Cybocephalus nipponicus+TX, Dacnusa sibirica+TX, Dacnusa sibirica (Minusa)+TX, Diglyphus isaea (Diminex)+TX, Delphastus catalinae (Delphastus)+TX, Delphastus pusillus+TX, Diachasmimorpha krausii+TX, Diachasmimorpha longicaudata+TX, Diaparsis jucunda+TX, Diaphorencyrtus aligarhensis+TX, Diglyphus isaea+TX, Diglyphus isaea (Miglyphus+TX, Digline)+TX, Dacnusa sibirica (DacDigline+TX, Minex)+TX, Diversinervus spp. +TX, Encarsia citrina+TX, Encarsia formosa (Encarsia Max+TX, Encarline+TX, En-Strip)+TX, Eretmocerus eremicus (Enermix)+TX, Encarsia guadeloupae+TX, Encarsia haitiensis+TX, Episyrphus balteatus (Syrphidend)+TX, Eretmoceris siphonini+TX, Eretmocerus califomicus+TX, Eretmocerus eremicus (Ercal+TX, Eretline)+TX, Eretmocerus eremicus (Bemimix)+TX, Eretmocerus hayati+TX, Eretmocerus mundus (Bemipar+TX, Eretline M)+TX, Eretmocerus siphonini+TX, Exochomus quadripustulatus+TX, Feltiella acarisuga (Spidend)+TX, Feltiella acarisuga (Feltiline)+TX, Fopius arisanus+TX, Fopius ceratitivorus+TX, Formononetin (Wirless Beehome)+TX, Franklinothrips vespiformis (Vespop)+TX, Galendromus occidentalis+TX, Goniozus legneri+TX, Habrobracon hebetor+TX, Harmonia axyridis (HarmoBeetle)+TX, Heterorhabditis spp. (Lawn Patrol)+TX, Heterorhabditis bacteriophora (NemaShield HB+TX, Nemaseek+TX, Terranem-Nam+TX, Terranem+TX, Larvanem+TX, B-Green+TX, NemAttack+TX, Nematop)+TX, Heterorhabditis megidis (Nemasys H+TX, BioNem H+TX, Exhibitline Hm+TX, Larvanem-M)+TX, Hippodamia convergens+TX, Hypoaspis aculeifer (Aculeifer-System+TX, Entomite-A)+TX, Hypoaspis miles (Hypoline M+TX, Entomite-M)+TX, Lbalia leucospoides+TX, Lecanoideus floccissimus+TX, Lemophagus errabundus+TX, Leptomastidea abnormis+TX, Leptomastix dactylopii (Leptopar)+TX, Leptomastix epona+TX, Lindorus lophanthae+TX, Lipolexis oregmae+TX, Lucilia caesar (Natufly)+TX, Lysiphlebus testaceipes+TX, Macrolophus caliginosus (Mirical-N+TX, Macroline C+TX, Mirical)+TX, Mesoseiulus longipes+TX, Metaphycus flavus+TX, Metaphycus lounsburyi+TX, Micromus angulatus (Milacewing)+TX, Microterys flavus+TX, Muscidifurax raptorellus and Spalangia cameroni (Biopar)+TX, Neodryinus typhlocybae+TX, Neoseiulus califomicus+TX, Neoseiulus cucumeris (THRYPEX))+TX, Neoseiulus fallacis+TX, Nesideocoris tenuis (NesidioBug+TX, Nesibug)+TX, Ophyra aenescens (Biofly)+TX, Orius insidiosus (Thripor-I+TX, Oriline I)+TX, Orius laevigatus (Thripor-L+TX, Oriline I)+TX, Orius majusculus (Oriline M)+TX, Orius strigicollis (Thripor-S)+TX, Pauesia juniperorum+TX, Pediobius foveolatus+TX, Phasmarhabditis hermaphrodita (Nemaslug)+TX, Phymastichus coffea+TX, Phytoseiulus macropilus+TX, Phytoseiulus persimilis (Spidex+TX, Phytoline P)+TX, Podisus maculiventris (Podisus)+TX, Pseudacteon curvatus+TX, Pseudacteon obtusus+TX, Pseudacteon tricuspis+TX, Pseudaphycus maculipennis+TX, Pseudleptomastix mexicana+TX, Psyllaephagus pilosus+TX, Psyttalia concolor (complex)+TX, Quadrastichus spp. +TX, Rhyzobius lophanthae+TX, Rodolia cardinalis+TX, Rumina decollate+TX, Semielacher petiolatus+TX, Sitobion avenae (Ervibank)+TX, Steinernema carpocapsae (Nematac C+TX, Millenium+TX, BioNem C+TX, NemAttack+TX, Nemastar+TX, Capsanem)+TX, Steinernema feltiae (NemaShield+TX, Nemasys F+TX, BioNem F+TX, Steinernema-System+TX, NemAttack+TX, Nemaplus+TX, Exhibitline Sf+TX, Scia-Rid+TX, Entonem)+TX, Steinernema kraussei (Nemasys L+TX, BioNem L+TX, Exhibitline Srb)+TX, Steinernema riobrave (BioVector+TX, BioVektor)+TX, Steinernema scapterisci (Nematac S)+TX, Steinernema spp. +TX, Steinernematid spp. (Guardian Nematodes)+TX, Stethorus punctillum (Stethorus)+TX, Tamarixia radiate+TX, Tetrastichus setifer+TX, Thripobius semiluteus+TX, Torymus sinensis+TX, Trichogramma brassicae (Tricholine B)+TX, Trichogramma brassicae (Tricho-Strip)+TX, Trichogramma evanescens+TX, Trichogramma minutum+TX, Trichogramma ostriniae+TX, Trichogramma platneri+TX, Trichogramma pretiosum+TX, Xanthopimpla stemmator; and

[0560] other biologicals including: abscisic acid+TX, bioSea+TX, Chondrostereum purpureum (Chontrol Paste)+TX, Colletotrichum gloeosporioides (Callego)+TX, Copper Octanoate (Cueva)+TX, Delta traps (Trapline D)+TX, Erwinia amylovora (Harpin) (ProAct+TX, Ni-HIBIT Gold CST)+TX, Ferri-phosphate (Ferramol)+TX, Funnel traps (Trapline Y)+TX, Gallex+TX, Grower's Secret+TX, Homo-brassonolide+TX, Iron Phosphate (Lilly Miller Worry Free Ferramol Slug & Snail Bait)+TX, MCP hail trap (Trapline F)+TX, Microctonus hyperodae+TX, Mycoleptodiscus terrestris (Des-X)+TX, BioGain+TX, Aminomite+TX, Zenox+TX, Pheromone trap (Thripline Ams)+TX, potassium bicarbonate (MilStop)+TX, potassium salts of fatty acids (Sanova)+TX, potassium silicate solution (SD-Matrix)+TX, potassium iodide+potassiumthiocyanate (Enzicur)+TX, SuffOil-X+TX, Spider venom+TX, Nosema locustae (Semaspore Organic Grasshopper Control)+TX, Sticky traps (Trapline YF+TX, Rebell Amarillo)+TX and Traps (Takitrapline y+B)+TX; or a biologically active compound or agent selected from: Brofluthrinate+TX, Diflovidazine +TX, Flometoquin+TX, Fluhexafon+TX, Plutella xylostella Granulosis virus+TX, Cydia pomonella Granulosis virus+TX, Imicyafos+TX, Heliothis virescens Nucleopolyhedrovirus+TX, Heliothis punctigera Nucleopolyhedrovirus+TX, Helicoverpa zea Nucleopolyhedrovirus+TX, Spodoptera frugiperda Nucleopolyhedrovirus+TX, Plutella xylostella Nucleopolyhedrovirus+TX, p-cymene+TX, Pyflubumide+TX, Pyrafluprole+TX, QRD 420+TX, QRD 452+TX, QRD 460+TX, Terpenoid blends+TX, Terpenoids+TX, Tetraniliprole+TX, and a-terpinene+TX;

[0561] or an active substance referenced by a code+TX, such as code AE 1887196 (BSC-BX60309)+TX, code NNI-0745 GR+TX, code IKI-3106+TX, code JT-L001+TX, code ZNQ-08056+TX, code IPPA152201+TX, code HNPC-A9908 (CAS: [660411-21-2])+TX, code HNPC-A2005 (CAS: [860028-12-2])+TX, code JS118+TX, code ZJ0967+TX, code ZJ2242+TX, code JS7119 (CAS: [929545-74-4])+TX, code SN-1172+TX, code HNPC-A9835+TX, code HNPC-A9955+TX, code HNPC-A3061+TX, code Chuanhua 89-1+TX, code IPP-10+TX, code ZJ3265+TX, code JS9117+TX, code ZJ3757+TX, code ZJ4042+TX, code ZJ4014+TX, code ITM-121+TX, code DPX-RAB55 (DKI-2301)+TX, code NA-89+TX, code MIE-1209+TX, code MCI-8007+TX, code BCS-CL73507+TX, code S-1871+TX, code DPX-RDS63+TX, Quinofumelin+TX, mefentrifluconazol+TX, fenpicoxamid+TX, fluindapyr+TX, inpyrfluxam+TX or indiflumetpyr+TX, isoflucypram+TX, pyrapropoyne+TX, florylpicoxamid+TX, metyltetraprole+TX, ipflufenoquin+TX, pyridachlometyl+TX or chlopyridiflu+TX, tetrachlorantraniliprole+TX, tetrachloraniliprole+TX, Tetflupyrolimet+TX, Triflufenpyrrolidone+TX, Tyclopyrazoflor+TX, flupyrimin+TX or pyrifluramide+TX, benzpyrimoxan +TX, beflubutamid-M+TX, Benzosufyl+TX or oxazosulfyl+TX, etpyrafen+TX, acynonapyr+TX or pyrinonafen+TX, oxotrione+TX, bixlozone+TX or clofendizone+TX or dicloroxizone+TX, cyclopyranil+TX or pyrazocyclonil+TX or cyclopyrazonil+TX, alpha-bromadiolone+TX, code AKD-1193+TX, Oxathiapiprolin+TX, Fluopyram+TX, Penflufen+TX, Fluoxopyrosad+TX, fluoxapiprolin+TX and Flupyradifurone+TX.

[0562] 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 ManualA 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.

[0563] 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.

[0564] The active ingredient mixture of the compounds of formula I selected from Tables A-1 to A-17, and B-1 to B-2 and Table P with active ingredients described above comprises a compound selected from Tables A-1 to A-17, and B-1 to B-2 and Table P 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.

[0565] 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 practised on the human or animal body.

[0566] The mixtures comprising a compound of formula I selected from Tables A-1 to A-17, and B-1 to B-2 and Table P 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 of formula I selected from Tables A-1 to A-17, and B-1 to B-2 and Table P and the active ingredients as described above is not essential for working the present invention.

[0567] 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.

[0568] 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.

[0569] 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 pouringwhich are to be selected to suit the intended aims of the prevailing circumstancesand 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.

[0570] 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.

[0571] 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.

[0572] 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.

[0573] The present invention also comprises seeds coated or treated with or containing a compound of formula I. 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 a compound of formula (I). Further, it is hereby made available, a composition comprising a plant propagation material treated with a compound of formula (I).

[0574] 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 formula (I) 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.

BIOLOGICAL EXAMPLES

[0575] The Examples which follow serve to illustrate the invention. Certain 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, 6 ppm, 3 ppm, 1.5 ppm, 0.8 ppm or 0.2 ppm.

Example B1: Bemisia tabaci (Cotton White Fly): Feeding/Contact Activity

[0576] Cotton leaf discs were placed on agar in 24-well microtiter plates and sprayed with aqueous test solutions prepared from 10,000 ppm DMSO stock solutions. After drying the leaf discs were infested with adult white flies. The samples were checked for mortality 6 days after incubation. The following compounds resulted in at least 80% mortality at an application rate of 200 ppm: P6, P14, P27, P45, and P46.

Example B2: Diabrotica Balteata (Corn Root Worm)

[0577] Maize sprouts placed onto an agar layer in 24-well microtiter plates were treated with aqueous test solutions prepared from 10,000 ppm DMSO stock solutions by spraying. After drying, the plates were infested with L2 larvae (6 to 10 per well). The samples were assessed for mortality and growth inhibition in comparison to untreated samples 4 days after infestation.

[0578] The following compounds gave an effect of at least 80% in at least one of the two categories (mortality or growth inhibition) at an application rate of 200 ppm:

[0579] P1, P2, P4, P6, P9, P10, P11, P12, P13, P14, P17, P20, P21, P23, P24, P25, P28, P29, P30, P32, P38, P40, P43, P44, P45, and P46.

Example B3: Euschistus heros (Neotropical Brown Stink Bug)

[0580] Soybean leaves on agar in 24-well microtiter plates were sprayed with aqueous test solutions prepared from 10,000 ppm DMSO stock solutions. After drying the leaves were infested with N2 nymphs. The samples were assessed for mortality and growth inhibition in comparison to untreated samples 5 days after infestation.

[0581] The following compounds gave an effect of at least 80% in at least one of the two categories (mortality or growth inhibition) at an application rate of 200 ppm:

[0582] P2, P4, P5, P6, P8, P9, P10, P11, P12, P13, P14, P15, P16, P17, P18, P20, P21, P22, P23, P24, P25, P26, P27, P28, P29, P30, P31, P32, P33, P34, P35, P36, P37, P38, P39, P40, P41, P42, P43, P44, P45, P46, and P47.

Example B4: Frankliniella occidentalis (Western Flower Thrips):Feeding/Contact Activity

[0583] Sunflower leaf discs were placed on agar in 24-well microtiter plates and sprayed with aqueous test solutions prepared from 10,000 DMSO stock solutions. After drying the leaf discs were infested with a Frankliniella population of mixed ages. The samples were assessed for mortality 7 days after infestation.

[0584] The following compounds resulted in at least 80% mortality at an application rate of 200 ppm: P1, P2, P4, P6, P9, P21, P43, and P46.

Example B5: Myzus persicae (Green peach aphid):Feeding/Contact Activity

[0585] 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.

[0586] The following compounds resulted in at least 80% mortality at an application rate of 200 ppm: P2, P4, P5, P6, P8, P9, P10, P11, P12, P13, P14, P15, P16, P17, P20, P21, P22, P23, P25, P26, P27, P28, P29, P30, P31, P32, P33, P34, P35, P36, P37, P38, P39, P40, P41, P42, P43, P44, P45, and P46.

Example B6: Myzus persicae (Green Peach Aphid). Systemic Activity

[0587] Roots of pea seedlings infested with an aphid population of mixed ages were placed directly into aqueous test solutions prepared from 10,000 DMSO stock solutions. The samples were assessed for mortality 6 days after placing seedlings into test solutions.

[0588] The following compounds resulted in at least 80% mortality at a test rate of 24 ppm:

[0589] P2, P4, P5, P6, P8, P9, P10, P11, P12, P13, P14, P15, P16, P17, P20, P21, P22, P23, P25, P26, P27, P28, P29, P30, P32, P34, P35, P36, P37, P38, P39, P40, P42, P43, P45, and P46.

Example B7: Plutella xylostella (Diamond Back Moth)

[0590] 24-well microtiter plates with artificial diet were treated with aqueous test solutions prepared from 10,000 ppm DMSO stock solutions by pipetting. After drying, the plates were infested with L2 larvae (10 to 15 per well). The samples were assessed for mortality and growth inhibition in comparison to untreated samples 5 days after infestation.

[0591] The following compounds gave an effect of at least 80% in at least one of the two categories (mortality or growth inhibition) at an application rate of 200 ppm:

[0592] P2, P5, P6, P9, P10, P11, P12, P13, P23, P24, P25, P26, P27, P29, P30, P34, P38, P40, P42, P43, and P45.

Example B8: Spodoptera littoralis (Egyptian Cotton Leaf Worm):Anti-Feeding Activity

[0593] 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 anti-feeding effect in comparison to untreated samples 3 days after infestation. Control of Spodoptera littoralis by a test sample is given when the anti-feedant effect is higher than the untreated sample.

[0594] The following compounds resulted in at least 80% control at an application rate of 200 ppm:

[0595] P6, P9, P10, P11, P12 and P13.

Example B9: Spodoptera littoralis (Egyptian Cotton Leaf Worm)

[0596] Cotton leaf discs were placed onto agar in 24-well microtiter plates and sprayed with aqueous test solutions prepared from 10,000 ppm DMSO stock solutions. After drying the leaf discs were infested with five L1 larvae. The samples were assessed for mortality, anti-feeding effect, and growth inhibition in comparison to untreated samples 3 days after infestation. Control of Spodoptera littoralis by a test sample is given when at least one of the categories mortality, anti-feedant effect, and growth inhibition is higher than the untreated sample.

[0597] The following compounds resulted in at least 80% control at an application rate of 200 ppm:

[0598] P5, P6, P9, P10, P11, P12, P13, P14, P17, P22, P23, P24, P29, P30, P34, P35, P40, P42, P43, and P45.

Example B10: Tetranychus urticae (Two-Spotted Spider Mite): Feeding/Contact Activity

[0599] 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.

[0600] The following compounds resulted in at least 80% mortality at an application rate of 200 ppm:

[0601] P6, P13, P21, P23, P38, P42, P45, and P46.

Example B11: Thrips tabaci (Onion Thrips) Feeding/Contact Activity

[0602] 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.

[0603] The following compounds resulted in at least 80% mortality at an application rate of 200 ppm:

[0604] P1 and P2.

Example B12: Plutella xylostella (Diamond Back Moth)

[0605] 24-well microtiter plates with artificial diet were treated with aqueous test solutions prepared from 10,000 ppm DMSO stock solutions by pipetting. After drying, Plutella eggs were pipetted through a plastic stencil onto a gel blotting paper and the plate was closed with it. The samples were assessed for mortality and growth inhibition in comparison to untreated samples 8 days after infestation. The following compounds gave an effect of at least 80% in at least one of the two categories (mortality or growth inhibition) at an application rate of 200 ppm: P46.

Example B13: Aedes aegypti (Yellow Fever Mosquito)

[0606] Test solutions, at an application rate of 200 ppm in ethanol, were applied to 12 well tissue culture plates. Once the deposits were dry, five, two to five day old adult female Aedes aegypti were added to each well, and sustained with a 10% sucrose solution in a cotton wool plug. Assessment of knockdown was made one hour after introduction, and mortality was assessed at 24 and 48 hours after introduction.

[0607] The following compounds gave at least 80% control of Aedes aegypti after 48h and/or 24h:

[0608] P2, and P4.

Example B14: Melodoigyne Incognita: Juvenile Mobility, In Vitro Profiling in 96 Well Plate

[0609] Test solutions are prepared from 10,000 ppm DMSO stock solutions with a TECAN robot to achieve 20 L of 1000, 200, 100, 50, 25 and 12.5 ppm. For each concentration three replicates are produced. Per well, 80 L nematode solution is added containing 100 to 150 freshly harvested second stage juveniles of Melodoigyne incognita. The plates are covered and stored at room temperature in the dark and incubated for 24 h. Mobility of the exposed juveniles in a treated well is measured using an imaging tool and compared to an average of 12 untreated replicates.

[0610] The following compounds achieved at least 80% control at 200 ppm after 24 h:

[0611] P5, P6, P9, P10, P11, P12, P13, P14, P15, P17, P19, P20, P21, P22, P23, P24, P25, P26, P27, P29, P30, P34, P36, P37, P38, P39, P40, P41, P42, P43, P44, and P45.

Example B15: Heterodera schachtii: Juvenile Mobility, In Vitro Profiling in 96 Well Plate

[0612] Test solutions are prepared from 10,000 ppm DMSO stock solutions with a TECAN robot to achieve 20 L of 500, 100, 50, 25, 12.5 and 6.25 ppm. For each concentration three replicates are produced. Per well, 80 L nematode solution is added containing 100 to 150 freshly harvested second stage juveniles of Heterodera schachtii. The plates are covered and stored at room temperature in the dark and incubated for 24 h. Mobility of the exposed juveniles in a treated well is measured using an imaging tool and compared to an average of 12 untreated replicates.

[0613] The following compounds achieved at least 80% control at 100 ppm after 24 h:

[0614] P28, and P45.

Example B16: Comparison of the Insecticidal Activity of Compound P4 According to the Invention with Compounds from the State of the Art

[0615] Activity of compound P4 according to the preparatory examples and of compound 4-9 from WO2016/104746 against Diabrotica balteata (Example B2) is summarized in Table B16:

TABLE-US-00014 TABLE B16 Concentration Compound (ppm) Insect Mortality (%) [00154] 200 Diabrotica balteata 100 [00155] 200 Diabrotica balteata 0

[0616] Table B16 shows that compounds P4 according to the invention exerts a substantially better insecticidal action on Diabrotica balteata than the compound from the state of the art. This enhanced effect was not to be expected on the basis of the structural similarity of these compounds.

Example B17: Comparison of the Insecticidal Activity of Compound P2 According to the Invention with Compounds from the State of the Art

[0617] Activity of compound P2 according to the preparatory examples and of compound 22 (table 23) from EP 3018130 against Myzus persicae (systemic, Example B6) is summarized in Table B17:

TABLE-US-00015 TABLE B17 Concentration Compound (ppm) Insect Mortality (%) [00156] 1.5 Myzus persicae (systemic) 80 [00157] 1.5 Myzus persicae (systemic) 0

[0618] Table B17 shows that compounds P2 according to the invention exerts a substantially better insecticidal action on Myzus persicae (systemic activity) than the compound from the state of the art. This enhanced effect was not to be expected on the basis of the structural similarity of these compounds.

Example B18: Comparison of the Insecticidal Activity of Compound P6 According to the Invention with Compounds from the State of the Art

[0619] Activity of compound P6 according to the preparatory examples and of compound 69 from WO2016/124557 against Myzus persicae (MYZUPE, contact, Example B19 below), Myzus persicae (MYZUPE, drench, Example B20 below), Nilaparvata lugens (NILALU, contact, Example B21 below), Frankliniella occidentalis (FRANOC, contact, Example B22 below) and Frankliniella occidentalis (FRANOC, drench, Example B23 below) is summarized in Table B18:

TABLE-US-00016 TABLE B18 Concentration Compound (ppm) Insect Mortality (%) [00158] 3 0.2 3 50 3 MYZUPE (contac) MYZUPE (drench) NILALU (contact) FRANOC (contact) FRANOC (drench) 70 92.5 80 98 92.5 [00159] 3 0.2 3 50 3 MYZUPE (contact) MYZUPE (drench) NILALU (contact) FRANOC (contact) FRANOC (drench) 20 50 30 0 35

Test Descriptions

Example B19: Myzus persicae (Green Peach Aphid), Mixed Population, Contact/Feeding

[0620] Pepper plants were infested with mixed aged aphid population and were treated 1 day after infestation with diluted test solutions in a spray chamber. 5 days after treatment samples were assessed for mortality.

Example B20: Myzus persicae (Green Peach Aphid), Mixed Population, Systemic into Soil

[0621] Pea seedlings cultivated in field soil and infested 1 day before treatment with mixed aged aphid population were treated as drench application and checked for mortality 7 days after treatment.

Example B21: Nilaparvata lugens (Brown Plant Hopper), Larvicide, Feeding/Contact

[0622] Rice plants were treated with the diluted test solutions in a spray chamber. After drying plants were infested with 20 N3 nymphs. 7 days after the treatment samples were assessed for mortality and growth regulation.

Example B22: Frankliniella occidentalis (Western Flower Thrips), Mixed Population, Contact/Feeding

[0623] French bean plants were treated with diluted test solutions in a spray chamber. After drying plants were infested with a mixed aged thrips population. 7 days after infestation, samples were assessed for mortality.

Example B23: Frankliniella occidentalis (Western Flower Thrips), Mixed Population, Systemic into Soil

[0624] French bean plants cultivated in field soil, were treated via drench application and 1 day after treatment they were infested with mixed aged thrips population. 8 days after infestation samples were assessed for mortality and phytotoxicity symptoms.

[0625] Table B18 shows that compounds P6 according to the invention exerts a substantially better insecticidal action on Myzus persicae (systemic activity) than the compound from the state of the art. This enhanced effect was not to be expected on the basis of the structural similarity of these compounds.

Example B24: Comparison of the Insecticidal Activity of Compounds P5, P21, P23, P34, P45, P36 and P37 According to the Invention with Compounds from the State of the Art

[0626] Activity of compound P5, P21, P23, P34, P45, P36 and P37 according to the preparatory examples and of compound P26 from WO2016030229 and compound 44 from WO2016/124563, respectively against Myzus persicae (feeding/contact, Example B5), Myzus persicae (systemic, Example B6) and Euschistus heros (Example B3) is summarized in Table B24:

TABLE-US-00017 TABLE B24 Concentration Compound (ppm) Insect Mortality (%) [00160] 12.5 1.5 50 Myzus persicae (feeding/contact) Myzus persicae (systemic) Euschistus heros 0 80 100 [00161] 12.5 1.5 50 Myzus persicae (feeding/contact) Myzus persicae (systemic) Eushistus heros 100 100 100 [00162] 12.5 1.5 50 Myzus persicae (feeding/contact) Myzus persicae (systemic) Euschistus heros 90 100 100 [00163] 12.5 1.5 50 Myzus persicae (feeding/contact) Myzus persicae (systemic) Euschistus heros 100 100 80 [00164] 12.5 1.5 50 Myzus persicae (feeding/contact) Myzus persicae (systemic) Euschistus heros 80 50 100 [00165] 12.5 1.5 50 Myzus (feeding/contact) Myzus persicae (systemic) Euschistus heros 90 100 100 [00166] 12.5 1.5 50 Myzus persicae (feeding/contact) Myzus persicae (systemic) Euschistus heros 90 100 100 [00167] 12.5 1.5 50 Myzus persicae (feeding/contact) Myzus persicae (systemic) Euschistus heros 0 0 50 [00168] 12.5 1.5 50 Myzus persicae (feeding/contact) Myzus persicae (systemic) Euschistus heros 80 0 50

[0627] Table B24 shows that compounds P5, P21, P23, P34, P45, P36 and P37 according to the invention exert a substantially better insecticidal action on Myzus persicae (feeding/contact and/or systemic activity) and/or Euschistus heros than the compound from the state of the art. This enhanced effect was not to be expected on the basis of the structural similarity of these compounds.