PESTICIDALLY ACTIVE HETEROCYCLIC DERIVATIVES WITH SULFUR CONTAINING SUBSTITUENTS

Abstract

Compounds of the formula (I), wherein the substituents are as defined in claim 1. Further-more, 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 in agriculture or horticulture for combating, preventing or controlling animal pests, including arthropods and in particular insects, molluscs, nematodes or representatives of the order Acarina.

##STR00001##

Claims

1. A compound of formula (I) ##STR00097## wherein R.sub.2 is C.sub.1-C.sub.6haloalkyl, C.sub.2-C.sub.6haloalkenyl or C.sub.1-C.sub.4haloalkylsulfonyl; R.sub.6 is C.sub.1-C.sub.6alkyl; Q is a radical selected from the group consisting of formula Qa and Qb ##STR00098## wherein the arrow denotes the point of attachment to the pyrimidinone ring; and wherein A represents CH or N; X is S, SO, SO.sub.2 or SO(NH); R.sub.1 is C.sub.1-C.sub.4alkyl or C.sub.3-C.sub.6cycloalkyl-C.sub.1-C.sub.4alkyl; Q.sub.1 is hydrogen, halogen, C.sub.1-C.sub.6haloalkyl, C.sub.3-C.sub.6cycloalkyl, C.sub.3-C.sub.6cycloalkyl monosubstituted by cyano, C.sub.1-C.sub.6cyanoalkyl, C.sub.1-C.sub.6cyanoalkoxy, C.sub.1-C.sub.6haloalkoxy, —N(R.sub.4).sub.2, —N(R.sub.4)COR.sub.5, —N(R.sub.4)CON(R.sub.4).sub.2, (oxazolidin-2-one)-3-yl or 2-pyridyloxy; or Q.sub.1 is a five- to six-membered aromatic ring system linked via a ring carbon atom to the ring which contains the substituent A, said ring system is unsubstituted or is mono- or polysubstituted by substituents selected from the group consisting of halogen, cyano, C.sub.1-C.sub.4alkyl, C.sub.1-C.sub.4haloalkyl, C.sub.1-C.sub.4alkoxy, C.sub.1-C.sub.4haloalkoxy, C.sub.1-C.sub.4alkylsulfanyl, C.sub.1-C.sub.4alkylsulfinyl and C.sub.1-C.sub.4alkylsulfonyl; and said ring system can contain 1, 2 or 3 ring heteroatoms selected from the group consisting of nitrogen, oxygen and sulphur, where said ring system may not contain more than one ring oxygen atom and not more than one ring sulfur atom; or Q.sub.1 is a five-membered aromatic ring system linked via a ring nitrogen atom to the ring which contains the substituent A, said ring system is unsubstituted or is mono- or polysubstituted by substituents selected from the group consisting of halogen, cyano, C.sub.1-C.sub.4alkyl, C.sub.1-C.sub.4haloalkyl, C.sub.1-C.sub.4alkoxy, C.sub.1-C.sub.4haloalkoxy, C.sub.1-C.sub.4alkylsulfanyl, C.sub.1-C.sub.4alkylsulfinyl and C.sub.1-C.sub.4alkylsulfonyl; and said ring system contains 1, 2 or 3 ring heteroatoms selected from the group consisting of nitrogen, oxygen and sulphur, where said ring system contains at least one ring nitrogen atom and may not contain more than one ring oxygen atom and not more than one ring sulfur atom; R.sub.3 is hydrogen, halogen or C.sub.1-C.sub.4alkyl; R.sub.4 is independently hydrogen, C.sub.1-C.sub.4alkyl or C.sub.3-C.sub.6cycloalkyl; R.sub.5 is C.sub.1-C.sub.6alkyl, C.sub.1-C.sub.6haloalkyl or C.sub.3-C.sub.6cycloalkyl; or an agrochemically acceptable salt, stereoisomer, enantiomer, tautomer or N-oxide of a compound of formula I.

2. A compound of formula I according to claim 1, wherein R.sub.2 is C.sub.1-C.sub.6haloalkyl, preferably —CH.sub.2CF.sub.2CHF.sub.2 or —CH.sub.2CF.sub.2CF.sub.3; R.sub.6 is C.sub.1-C.sub.3alkyl, preferably methyl; Q is a radical selected from the group consisting of formula Qa and Qb, wherein A is N; and Q.sub.1 is hydrogen, halogen, C.sub.3-C.sub.6cycloalkyl, C.sub.3-C.sub.6cycloalkyl monosubstituted by cyano, C.sub.1-C.sub.6cyanoalkyl, —N(R.sub.4).sub.2, —N(R.sub.4)COR.sub.5 or —N(R.sub.4)CON(R.sub.4).sub.2, all in which R.sub.4 is independently either hydrogen or C.sub.1-C.sub.4alkyl (preferably hydrogen or methyl) and R.sub.5 is C.sub.1-C.sub.6alkyl or C.sub.3-C.sub.6cycloalkyl (preferably methyl or cyclopropyl), 2-pyridyloxy, or 1,2,4-triazol-1-yl; preferably Q.sub.1 is hydrogen, chlorine, bromine, cyclopropyl, 1-cyanocyclopropyl, 1-cyano-1-methyl-ethyl, —NH(CH.sub.3), —N(CH.sub.3)COCH.sub.3, —N(CH.sub.3)CO(cyclopropyl), —N(CH.sub.3)CONH(CH.sub.3), 2-pyridyloxy or 1,2,4-triazol-1-yl.

3. A compound of formula I according to claim 1, wherein R.sub.2 is C.sub.1-C.sub.6haloalkyl, preferably —CH.sub.2CF.sub.2CHF.sub.2 or —CH.sub.2CF.sub.2CF.sub.3; R.sub.6 is methyl; Q is a radical selected from the group consisting of formula Qa and Qb, wherein A is N; and Q.sub.1 is hydrogen, bromine, cyclopropyl, 1-cyanocyclopropyl, 1-cyano-1-methyl-ethyl, 2-pyridyloxy or —N(CH.sub.3)COCH.sub.3 when Q is Qa; or Q.sub.1 is hydrogen, chlorine, —NH(CH.sub.3), —N(CH.sub.3)COCH.sub.3, —N(CH.sub.3)CO(cyclopropyl), —N(CH.sub.3)CONH(CH.sub.3) or 1,2,4-triazol-1-yl, when Q is Qb.

4. A compound of formula I according to claim 1, represented by the compounds of formula (I-2) ##STR00099## wherein X, R.sub.1 and R.sub.2 are as defined under formula I in claim 1, and wherein Q.sub.1 is hydrogen, halogen, C.sub.1-C.sub.6haloalkyl, C.sub.3-C.sub.6cycloalkyl, C.sub.3-C.sub.6cycloalkyl monosubstituted by cyano, C.sub.1-C.sub.6cyanoalkyl, C.sub.1-C.sub.6haloalkoxy, —N(R.sub.4).sub.2, —N(R.sub.4)COR.sub.5, or —N(R.sub.4)CON(R.sub.4).sub.2, (oxazolidin-2-one)-3-yl or 2-pyridyloxy; or Q.sub.1 is a five- to six-membered aromatic ring system linked via a ring carbon atom to the pyridyl ring substituted by X—R.sub.1, said ring system is unsubstituted or is mono-substituted by substituents selected from the group consisting of halogen, cyano and C.sub.1-C.sub.4haloalkyl; and said ring system can contain 1 or 2 ring nitrogen atoms; or Q.sub.1 is a five-membered aromatic ring system linked via a ring nitrogen atom to the pyridyl ring substituted by X—R.sub.1, said ring system is unsubstituted or is mono-substituted by substituents selected from the group consisting of halogen, cyano and C.sub.1-C.sub.4haloalkyl; and said ring system contains 2 or 3 ring nitrogen atoms; each R.sub.4 is independently preferably hydrogen or C.sub.1-C.sub.4alkyl; and R.sub.5 is preferably C.sub.1-C.sub.6alkyl or C.sub.3-C.sub.6cycloalkyl.

5. A compound of formula I according to claim 1, represented by the compounds of formula (I-3) ##STR00100## wherein X, R.sub.1 and R.sub.2 are as defined under formula I in claim 1, and wherein Q.sub.1 is hydrogen, halogen, C.sub.1-C.sub.6haloalkyl, C.sub.3-C.sub.6cycloalkyl, C.sub.3-C.sub.6cycloalkyl monosubstituted by cyano, C.sub.1-C.sub.6cyanoalkyl, C.sub.1-C.sub.6haloalkoxy, —N(R.sub.4).sub.2, —N(R.sub.4)COR.sub.5, or —N(R.sub.4)CON(R.sub.4).sub.2, (oxazolidin-2-one)-3-yl or 2-pyridyloxy; or Q.sub.1 is a five- to six-membered aromatic ring system linked via a ring carbon atom to the phenyl ring substituted by X—R.sub.1, said ring system is unsubstituted or is mono-substituted by substituents selected from the group consisting of halogen, cyano and C.sub.1-C.sub.4haloalkyl; and said ring system can contain 1 or 2 ring nitrogen atoms; or Q.sub.1 is a five-membered aromatic ring system linked via a ring nitrogen atom to the phenyl ring substituted by X—R.sub.1, said ring system is unsubstituted or is mono-substituted by substituents selected from the group consisting of halogen, cyano and C.sub.1-C.sub.4haloalkyl; and said ring system contains 2 or 3 ring nitrogen atoms; each R.sub.4 is independently preferably hydrogen or C.sub.1-C.sub.4alkyl; and R.sub.5 is preferably C.sub.1-C.sub.6alkyl or C.sub.3-C.sub.6cycloalkyl.

6. A compound of formula I according to claim 1, represented by the compounds of formula (I-4) ##STR00101## wherein A is CH or N, preferably N; R.sub.2 is C.sub.1-C.sub.6haloalkyl, preferably —CH.sub.2CF.sub.2CHF.sub.2 or —CH.sub.2CF.sub.2CF.sub.3; R.sub.3 is hydrogen or C.sub.1-C.sub.4alkyl, preferably hydrogen or methyl; Q.sub.1 is hydrogen, halogen, C.sub.1-C.sub.6haloalkyl, C.sub.3-C.sub.6cycloalkyl, C.sub.3-C.sub.6cycloalkyl monosubstituted by cyano, C.sub.1-C.sub.6cyanoalkyl, C.sub.1-C.sub.6haloalkoxy, —N(R.sub.4).sub.2, —N(R.sub.4)COR.sub.5, or —N(R.sub.4)CON(R.sub.4).sub.2, (oxazolidin-2-one)-3-yl or 2-pyridyloxy; or Q.sub.1 is a five- to six-membered aromatic ring system linked via a ring carbon atom to the ring which contains the substituent A, said ring system is unsubstituted or is mono-substituted by substituents selected from the group consisting of halogen, cyano and C.sub.1-C.sub.4haloalkyl; and said ring system can contain 1 or 2 ring nitrogen atoms; or Q.sub.1 is a five-membered aromatic ring system linked via a ring nitrogen atom to the ring which contains the substituent A, said ring system is unsubstituted or is mono-substituted by substituents selected from the group consisting of halogen, cyano and C.sub.1-C.sub.4haloalkyl; and said ring system contains 2 or 3 ring nitrogen atoms; each R.sub.4 is independently hydrogen or C.sub.1-C.sub.4alkyl, preferably hydrogen or methyl; and R.sub.5 is C.sub.1-C.sub.6alkyl or C.sub.3-C.sub.6cycloalkyl, preferably methyl or cyclopropyl.

7. A compound of formula I according to claim 1, represented by the compounds of formula (I-6) ##STR00102## wherein X, R.sub.1 and R.sub.2 are as defined under formula I in claim 1, and wherein Q.sub.1 is hydrogen, halogen, C.sub.1-C.sub.6haloalkyl, C.sub.3-C.sub.6cycloalkyl, C.sub.3-C.sub.6cycloalkyl monosubstituted by cyano, C.sub.1-C.sub.6cyanoalkyl, C.sub.1-C.sub.6haloalkoxy, —N(R.sub.4).sub.2, —N(R.sub.4)COR.sub.5, or —N(R.sub.4)CON(R.sub.4).sub.2, (oxazolidin-2-one)-3-yl or 2-pyridyloxy; or Q.sub.1 is a five- to six-membered aromatic ring system linked via a ring carbon atom to the pyridyl ring substituted by X—R.sub.1, said ring system is unsubstituted or is mono-substituted by substituents selected from the group consisting of halogen, cyano and C.sub.1-C.sub.4haloalkyl; and said ring system can contain 1 or 2 nitrogen atoms; or Q.sub.1 is a five-membered aromatic ring system linked via a ring nitrogen atom to the pyridyl ring substituted by X—R.sub.1, said ring system is unsubstituted or is mono-substituted by substituents selected from the group consisting of halogen, cyano and C.sub.1-C.sub.4haloalkyl; and said ring system contains 2 or 3 nitrogen atoms; R.sub.4 is independently preferably hydrogen or C.sub.1-C.sub.4alkyl; and R.sub.5 is preferably C.sub.1-C.sub.6alkyl or C.sub.3-C.sub.6cycloalkyl.

8. A compound of formula I according to claim 1, represented by the compounds of formula (I-7) ##STR00103## wherein X, R.sub.1 and R.sub.2 under formula I in claim 1, and wherein Q.sub.1 is hydrogen, halogen, C.sub.1-C.sub.6haloalkyl, C.sub.3-C.sub.6cycloalkyl, C.sub.3-C.sub.6cycloalkyl monosubstituted by cyano, C.sub.1-C.sub.6cyanoalkyl, C.sub.1-C.sub.6haloalkoxy, —N(R.sub.4).sub.2, —N(R.sub.4)COR.sub.5, or —N(R.sub.4)CON(R.sub.4).sub.2, (oxazolidin-2-one)-3-yl or 2-pyridyloxy; or Q.sub.1 is a five- to six-membered aromatic ring system linked via a ring carbon atom to the phenyl ring substituted by X—R.sub.1, said ring system is unsubstituted or is mono-substituted by substituents selected from the group consisting of halogen, cyano and C.sub.1-C.sub.4haloalkyl; and said ring system can contain 1 or 2 ring nitrogen atoms; or Q.sub.1 is a five-membered aromatic ring system linked via a ring nitrogen atom to the phenyl ring substituted by X—R.sub.1, said ring system is unsubstituted or is mono-substituted by substituents selected from the group consisting of halogen, cyano and C.sub.1-C.sub.4haloalkyl; and said ring system contains 2 or 3 ring nitrogen atoms; R.sub.4 is independently preferably hydrogen or C.sub.1-C.sub.4alkyl; and R.sub.5 is preferably C.sub.1-C.sub.6alkyl or C.sub.3-C.sub.6cycloalkyl.

9. A compound of formula I according to claim 1, represented by the compounds of formula (I-8) ##STR00104## wherein A is CH or N, preferably N; R.sub.2 is C.sub.1-C.sub.6haloalkyl, preferably —CH.sub.2CF.sub.2CHF.sub.2 or —CH.sub.2CF.sub.2CF.sub.3; R.sub.3 is hydrogen or C.sub.1-C.sub.4alkyl, preferably hydrogen or methyl; Q.sub.1 is hydrogen, halogen, C.sub.1-C.sub.6haloalkyl, C.sub.3-C.sub.6cycloalkyl, C.sub.3-C.sub.6cycloalkyl monosubstituted by cyano, C.sub.1-C.sub.6cyanoalkyl, C.sub.1-C.sub.6haloalkoxy, —N(R.sub.4).sub.2, —N(R.sub.4)COR.sub.5, or —N(R.sub.4)CON(R.sub.4).sub.2, (oxazolidin-2-one)-3-yl or 2-pyridyloxy; or Q.sub.1 is a five- to six-membered aromatic ring system linked via a ring carbon atom to the ring which contains the substituent A, said ring system is unsubstituted or is mono-substituted by substituents selected from the group consisting of halogen, cyano and C.sub.1-C.sub.4haloalkyl; and said ring system can contain 1 or 2 ring nitrogen atoms; or Q.sub.1 is a five-membered aromatic ring system linked via a ring nitrogen atom to the ring which contains the substituent A, said ring system can be mono-substituted by substituents selected from the group consisting of halogen, cyano or C.sub.1-C.sub.4haloalkyl; and said ring system contains 2 or 3 ring nitrogen atoms; R.sub.4 is independently hydrogen or C.sub.1-C.sub.4alkyl, preferably hydrogen or methyl; and R.sub.5 is C.sub.1-C.sub.6alkyl or C.sub.3-C.sub.6cycloalkyl, preferably methyl or cyclopropyl.

10. A compound of formula I as claimed in claim 1, wherein R.sub.2 is —CH.sub.2CF.sub.2CHF.sub.2 or —CH.sub.2CF.sub.2CF.sub.3.

11. A compound of formula I as claimed in claim 1, wherein Q.sub.1 is hydrogen, halogen, trifluoromethyl, cyclopropyl, cyanocyclopropyl, cyanoisopropyl, trifluoroethoxy, —N(R.sub.4).sub.2, —N(R.sub.4)COR.sub.5, or —N(R.sub.4)CON(R.sub.4).sub.2, in each of which R.sub.4 is independently either hydrogen or methyl and R.sub.5 is either methyl or cyclopropyl, or Q.sub.1 is (oxazolidin-2-one)-3-yl, 2-pyridyloxy, N-linked pyrazolyl which can be mono-substituted by chloro, cyano or trifluoromethyl; or Q.sub.1 is N-linked triazolyl or C-linked pyrimidinyl.

12. A compound of formula I as claimed in claim 1, wherein Q.sub.1 is hydrogen, chlorine, bromine, trifluoromethyl, cyclopropyl, 1-cyanocyclopropyl, 1-cyano-1-methyl-ethyl, 2,2,2-trifluoroethoxy, —NH(CH.sub.3), —N(CH.sub.3)COCH.sub.3, —N(CH.sub.3)CO(cyclopropyl), —N(H)CONH(CH.sub.3), —N(CH.sub.3)CONH(CH.sub.3), (oxazolidin-2-one)-3-yl, 2-pyridyloxy, pyrazol-1-yl, 3-chloro-pyrazol-1-yl, 3-cyano-pyrazol-1-yl, 3-trifluoromethyl-pyrazol-1-yl, 1,2,4-triazol-1-yl or pyrimidin-2-yl.

13. A compound of formula I as claimed in claim 1, wherein A is N; and Q.sub.1 is hydrogen, chlorine, bromine, cyclopropyl, 1-cyanocyclopropyl, 1-cyano-1-methyl-ethyl, —NH(CH.sub.3), —N(CH.sub.3)COCH.sub.3, —N(CH.sub.3)CO(cyclopropyl), —N(CH.sub.3)CONH(CH.sub.3), 2-pyridyloxy or 1,2,4-triazol-1-yl.

14. A compound of formula I as claimed in claim 1, selected from the group consisting of: 2-(3-ethylsulfanyl-2-pyridyl)-3-methyl-5-(2,2,3,3,3-pentafluoropropoxy)pyrimidin-4-one (Compound P1); 2-(3-ethylsulfonyl-2-pyridyl)-3-methyl-5-(2,2,3,3,3-pentafluoropropoxy)pyrimidin-4-one (Compound P2); 2-(5-bromo-3-ethylsulfanyl-2-pyridyl)-3-methyl-5-(2,2,3,3,3-pentafluoropropoxy)pyrimidin-4-one (Compound P3); N-[5-ethylsulfanyl-6-[1-methyl-6-oxo-5-(2,2,3,3,3-pentafluoropropoxy)pyrimidin-2-yl]-3-pyridyl]-N-methyl-acetamide (Compound P4); N-[5-ethylsulfonyl-6-[1-methyl-6-oxo-5-(2,2,3,3,3-pentafluoropropoxy)pyrimidin-2-yl]-3-pyridyl]-N-methyl-acetamide (Compound P5); 2-(6-chloro-3-ethylsulfanyl-2-pyridyl)-3-methyl-5-(2,2,3,3,3-pentafluoropropoxy)pyrimidin-4-one (Compound P6); 2-(6-chloro-3-ethylsulfonyl-2-pyridyl)-3-methyl-5-(2,2,3,3,3-pentafluoropropoxy)pyrimidin-4-one (Compound P7); 2-[3-ethylsulfonyl-6-(methylamino)-2-pyridyl]-3-methyl-5-(2,2,3,3,3-pentafluoropropoxy)pyrimidin-4-one (Compound P8); N-[5-ethylsulfonyl-6-[1-methyl-6-oxo-5-(2,2,3,3,3-pentafluoropropoxy)pyrimidin-2-yl]-2-pyridyl]-N-methyl-acetamide (Compound P9); 1-[5-ethylsulfanyl-6-[1-methyl-6-oxo-5-(2,2,3,3,3-pentafluoropropoxy)pyrimidin-2-yl]-3-pyridyl]cyclopropanecarbonitrile (Compound P10); 1-[5-ethylsulfonyl-6-[1-methyl-6-oxo-5-(2,2,3,3,3-pentafluoropropoxy)pyrimidin-2-yl]-3-pyridyl]cyclopropanecarbonitrile (Compound P11); 2-[5-ethylsulfanyl-6-[1-methyl-6-oxo-5-(2,2,3,3,3-pentafluoropropoxy)pyrimidin-2-yl]-3-pyridyl]-2-methyl-propanenitrile (Compound P12); 2-[5-ethylsulfonyl-6-[1-methyl-6-oxo-5-(2,2,3,3,3-pentafluoropropoxy)pyrimidin-2-yl]-3-pyridyl]-2-methyl-propanenitrile (Compound P13); 2-[3-ethylsulfonyl-6-(1,2,4-triazol-1-yl)-2-pyridyl]-3-methyl-5-(2,2,3,3,3-pentafluoropropoxy)pyrimidin-4-one (Compound P14); 1-[5-ethylsulfonyl-6-[1-methyl-6-oxo-5-(2,2,3,3,3-pentafluoropropoxy)pyrimidin-2-yl]-2-pyridyl]-1,3-dimethyl-urea (Compound P15); N-[5-ethylsulfonyl-6-[1-methyl-6-oxo-5-(2,2,3,3,3-pentafluoropropoxy)pyrimidin-2-yl]-2-pyridyl]-N-methyl-cyclopropanecarboxamide (Compound P16); 2-(5-cyclopropyl-3-ethylsulfanyl-2-pyridyl)-3-methyl-5-(2,2,3,3,3-pentafluoropropoxy)pyrimidin-4-one (Compound P17); 2-(5-cyclopropyl-3-ethylsulfonyl-2-pyridyl)-3-methyl-5-(2,2,3,3,3-pentafluoropropoxy)pyrimidin-4-one (Compound P18); 2-[3-ethylsulfanyl-5-(2-pyridyloxy)-2-pyridyl]-3-methyl-5-(2,2,3,3,3-pentafluoropropoxy)pyrimidin-4-one (Compound P19); and 2-[3-ethylsulfonyl-5-(2-pyridyloxy)-2-pyridyl]-3-methyl-5-(2,2,3,3,3-pentafluoropropoxy)pyrimidin-4-one (Compound P20).

15. 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.

16. 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 or a composition as defined claim 15.

17. 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 15.

18. A compound of formula IV-Qa or a compound of formula IV-Qb ##STR00105## or a salt thereof, wherein Q.sub.1 and R.sub.1 are as defined under formula I in claim 1.

19. A compound of formula V ##STR00106## or a tautomeric form thereof, wherein R.sub.2 is C.sub.1-C.sub.6fluoroalkyl, and Rx is C.sub.1-C.sub.6alkyl.

Description

PREPARATORY EXAMPLES

[0604] “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 and/or GCMS methods below was used to characterize the compounds. The characteristic LCMS and GCMS values obtained for each compound were the retention time (“Rt”, recorded in minutes) and the measured molecular ion (M+H).sup.+ or (M−H).sup.−.

[0605] LCMS and GCMS Methods:

[0606] Method 1:

[0607] Spectra were recorded on a Mass Spectrometer from Waters (ZQ Single quadrupole mass spectrometer) equipped with an electrospray source (Polarity: positive or negative ions, Capillary: 3.00 kV, Cone range: 30-60 V, Extractor: 2.00 V, Source Temperature: 150° C., Desolvation Temperature: 350° C., Cone Gas Flow: 0 L/Hr, Desolvation Gas Flow: 650 L/Hr, Mass range: 100 to 900 Da) and an Acquity UPLC from Waters: Binary pump, heated column compartment and diode-array detector. Solvent degasser, binary pump, heated column compartment and diode-array detector. Column: Waters UPLC HSS T3, 1.8 m, 30×2.1 mm, Temp: 60° C., DAD Wavelength range (nm): 210 to 500, Solvent Gradient: A=water+5% MeOH+0.05% HCOOH, B=Acetonitrile+0.05% HCOOH: gradient: 0 min 0% B, 100% A; 1.2-1.5 min 100% B; Flow (ml/min) 0.85.

[0608] Method 2:

[0609] Spectra were recorded on a Mass Spectrometer from Waters (SQD or ZQ Single quadrupole mass spectrometer) equipped with an electrospray source (Polarity: positive or negative ions, Capillary: 3.00 kV, Cone range: 30-60 V, Extractor: 2.00 V, Source Temperature: 150° C., Desolvation Temperature: 350° C., Cone Gas Flow: 0 L/Hr, Desolvation Gas Flow: 650 L/Hr, Mass range: 100 to 900 Da) and an Acquity UPLC from Waters: Binary pump, heated column compartment and diode-array detector. Solvent degasser, binary pump, heated column compartment and diode-array detector. Column: Waters UPLC HSS T3, 1.8 m, 30×2.1 mm, Temp: 60° C., DAD Wavelength range (nm): 210 to 500, Solvent Gradient: A=water+5% MeOH+0.05% HCOOH, B=Acetonitrile+0.05% HCOOH; gradient: 0 min 0% B, 100% A; 2.7-3.0 min 100% B; Flow (ml/min) 0.85.

[0610] Method 3:

[0611] GCMS analyses were performed on a Thermo Electron instrument where a TRACE GC ULTRA gas chromatograph (equipped with a Zebron Phenomenex ZB-5 ms 15 m, diam: 0.25 mm, 0.25 μm column; H.sub.2 flow 1.2 mL/min, temp injector: 250° C., temp detector: 220° C.; method: start at 40° C., then 40° C./min until 320° C., hold 2 min at 320° C.) was linked to a DSQ mass spectrometer characterizing the compounds by chemical ionization in the positive ion mode (CI+) using methane as a reagent gas.

Example H1: Preparation of 2-(3-ethylsulfanyl-2-pyridyl)-3-methyl-5-(2,2,3,3,3-pentafluoro-propoxy)pyrimidin-4-one (Compound P1)

[0612] ##STR00041##

Step 1: Preparation of Methyl 2-(2,2,3,3,3-pentafluoropropoxy)acetate (Intermediate I1)

[0613] ##STR00042##

[0614] Potassium carbonate (5.42 g, 39.2 mmol, 1.2 eq.) was added to a mixture of 2,2,3,3,3-pentafluoro-1-propanol (3.95 mL, 39.2 mmol, 1.2 eq.) and methyl 2-bromoacetate (3.01 mL, 32.7 mmol) in acetonitrile (40.0 mL) at room temperature. The reaction mixture was stirred for 2 hours, then filtered. The filtrate was concentrated, diluted with water and the aqueous phase extracted twice with ethyl acetate. The combined organic layers were washed with an aqueous saturated sodium hydrogeno-carbonate solution, dried over magnesium sulfate, filtered and concentrated under vacuum. The crude yellow oil was used without further purification. .sup.1H NMR (400 MHz, CDCl.sub.3) δ ppm: 3.79 (s, 3H), 4.11 (m, 2H), 4.27 (s, 2H).

Step 2: Preparation of a Mixture of Ethyl and Methyl 3-oxo-2-(2,2,3,3,3-pentafluoropropoxy)propanoate (Intermediate I2)

[0615] ##STR00043##

[0616] Methyl 2-(2,2,3,3,3-pentafluoropropoxy)acetate (intermediate 11 prepared above) (1.98 g, 8.91 mmol) and ethyl formate (1.25 mL, 15.2 mmol, 1.7 eq.) were added to a mixture of sodium (freshly cut, 311 mg, 13.4 mmol, 1.5 eq.) in diethyl ether (8.9 mL) under argon atmosphere. The reaction mixture was heated at reflux, generating a gas evolution when reaching 30° C. After 2 hours at reflux, the mixture was cooled to room temperature and carefully quenched with iced water. The aqueous phase was extracted twice with diethyl ether, then acidified to pH ca. 5 by addition of an aqueous 1 M hydrochloric acid solution, and extracted again twice with diethyl ether. The combined organic phases were washed with a saturated sodium hydrogenocarbonate aqueous solution, dried over magnesium sulfate, filtered and concentrated under vacuum to give a crude mixture of ethyl and methyl 3-oxo-2-(2,2,3,3,3-pentafluoropropoxy)propanoate as a yellow oil, which was used without further purification. GCMS (method 3): 251 (M+H).sup.+, retention time 4.11 min for the methyl ester; respectively 265 (M+H).sup.+, retention time 4.40 min for the ethyl ester.

Step 3: Preparation of 3-ethylsulfanylpyridine-2-carboxamidine (Intermediate I3)

[0617] ##STR00044##

[0618] A 2.0 M trimethylaluminum solution in toluene (37.0 mL, 74.0 mmol, 1.22 eq.) was added dropwise to a suspension of ammonium hydrochloride (3.91 g, 74.0 mmol, 1.22 eq.) in toluene (100 mL) at 0° C. After stirring for 30 minutes, a solution of 3-ethylsulfanylpyridine-2-carbonitrile (prepared as described in WO14/104407) (60.9 mmol, 10.0 g) in toluene (15.0 mL) was added dropwise, and the reaction mixture was heated at 90° C. and stirred overnight. After cooling to room temperature, ethyl acetate was added, and the reaction mixture was carefully quenched by dropwise addition of a 4 N sodium hydroxide aqueous solution at 0° C. The aqueous phase was extracted twice with ethyl acetate, the combined organic layers were dried over sodium sulfate, filtered and concentrated to give a first crop of the desired crude amidine 13. The aqueous phase was saturated with sodium chloride and thoroughly extracted three times with ethyl acetate and three times with dichloromethane. The combined organic layers were dried over sodium sulfate, filtered and concentrated to give another portion of crude 3-ethylsulfanylpyridine-2-carboxamidine. Both crude materials were used directly in the next step without further purification. LCMS (method 1): 182 (M+H).sup.+, Rt 0.18 min.

Step 4: Preparation of 2-(3-ethylsulfanyl-2-pyridyl)-5-(2,2,3,3,3-pentafluoropropoxy)pyrimidin-4-ol (Intermediate I4)

[0619] ##STR00045##

[0620] A 5.40 M sodium methanolate solution in methanol (0.562 mL, 3.03 mmol, 1.1 eq.) was added to a solution of crude mixture of ethyl and methyl 3-oxo-2-(2,2,3,3,3-pentafluoropropoxy)propanoate (intermediate 12 prepared above in step 2) (0.793 g, estimated 3.17 mmol, 1.15 eq.) and crude 3-ethylsulfanylpyridine-2-carboxamidine (intermediate 13 prepared above in step 3) (0.50 g, 2.76 mmol) in methanol (9.8 mL). The reaction mixture was heated at reflux for 2 hours. After cooling to room temperature, the mixture was quenched with acetic acid (0.19 mL, 3.31 mmol, 1.20 eq.), diluted with water, and the aqueous phase was extracted twice with ethyl acetate. The combined organic phases were washed with a saturated ammonium chloride aqueous solution, dried over magnesium sulfate, filtered and concentrated. The residue was purified by flash chromatography over silica gel (ethyl acetate in cyclohexane) to afford the desired product as a beige solid. LCMS (method 1): 382 (M+H).sup.+, Rt 1.00 min.

Step 5: Preparation of 2-(3-ethylsulfanyl-2-pyridyl)-3-methyl-5-(2,2,3,3,3-pentafluoro-propoxy)pyrimidin-4-one (Compound P1)

[0621] ##STR00046##

[0622] Iodomethane (0.373 mL, 6.0 mmol, 4.0 eq.) was added to a suspension of 2-(3-ethylsulfanyl-2-pyridyl)-5-(2,2,3,3,3-pentafluoropropoxy)pyrimidin-4-ol (intermediate 14 prepared above) (0.572 g, 1.50 mmol) and potassium carbonate (0.303 g, 3.0 mmol, 2.0 eq.) in dimethylformamide (12.0 mL) in a microwave vial. The reaction mixture was degassed and filled with argon, the vial was caped and the reaction mixture heated at 100° C. for 1 hour. After cooling to room temperature, the reaction mixture was poured into water, the aqueous phase was extracted three times with ethyl acetate, the combined organic phases were dried over magnesium sulfate, filtered and concentrated. The residue was purified by flash chromatography over silica gel (ethyl acetate in cyclohexane) to afford the desired compound P1 as an amber gum. LCMS (method 1): 396 (M+H).sup.+, Rt 0.97 min.

Example H2: Preparation of 2-(3-ethylsulfonyl-2-pyridyl)-3-methyl-5-(2,2,3,3,3-pentafluoro-propoxy)pyrimidin-4-one (Compound P2)

[0623] ##STR00047##

[0624] 3-Chloroperbenzoic acid (0.319 g, 1.39 mmol, 2.30 eq.) was added portionwise to a 0° C. cooled solution of 2-(3-ethylsulfanyl-2-pyridyl)-3-methyl-5-(2,2,3,3,3-pentafluoropropoxy)pyrimidin-4-one (compound P1 prepared as described above) (0.238 g, 0.602 mmol) in ethyl acetate (2.4 mL). After stirring for 16 hours at room temperature, the reaction mixture was quenched with a 10% w/w aqueous sodium thiosulfate solution. A saturated sodium hydrogenocarbonate aqueous solution was added after stirring for 10 minutes, and the aqueous phase was extracted twice with ethyl acetate. The combined organic phases were dried over magnesium sulfate, filtered and concentrated. The crude material was purified by flash chromatography over silica gel (ethyl acetate in cyclohexane) to give the desired product as a white solid (181 mg). LCMS (method 1): 428 (M+H).sup.+, Rt 0.89 min.

Example H3: Preparation of 2-(5-bromo-3-ethylsulfanyl-2-pyridyl)-3-methyl-5-(2,2,3,3,3-pentafluoropropoxy)pyrimidin-4-one (Compound P3)

[0625] ##STR00048##

Step 1: Preparation of 5-bromo-3-ethylsulfanyl-pyridine-2-carboxamidine (Intermediate I5)

[0626] ##STR00049##

[0627] To a suspension of ammonium hydrochloride (9.35 g, 175 mmol, 2.50 equiv.) in toluene (170 mL) was added dropwise at 0° C. trimethylaluminium (2 M in toluene, 77.0 mL, 154 mmol, 2.20 equiv.). The reaction mixture was allowed to reach room temperature and kept stirring after no more gas evolution occurred. Then a solution of 5-bromo-3-ethylsulfanyl-pyridine-2-carbonitrile (CAS 1879106-77-0) (17.0 g, 69.9 mmol) in toluene (26 mL) was added to the reaction mixture. It was heated up to 90° C. and stirred overnight. After cooling down to 0° C., methanol (150 mL) was added portionwise, followed by a mixture of methanol:water (120 mL, 4:1). It was then stirred at room temperature for 1 hour. The resulting suspension was filtered and the filtrate was concentrated to afford the desired crude amidine 15, which was used directly in the next step without further purification. LCMS (method 1): 260/262 (M+H).sup.+ (bromo pattern), Rt 0.25 min.

Step 2: Preparation of Methyl 2-(2,2,3,3,3-pentafluoropropoxy)acetate (Intermediate I1)

[0628] ##STR00050##

[0629] To a mixture of 2,2,3,3,3-pentafluoro-1-propanol (CAS 422-05-9) (39.5 mL, 392 mmol, 1.20 eq.) and methyl 2-bromoacetate (30.9 mL, 327 mmol) in acetonitrile (150 mL) was added at room temperature potassium carbonate (54.2 g, 392 mmol, 1.20 eq.). The reaction mixture was heated up to 50° C. and stirred overnight. After cooling down to room temperature, it was extracted three times with pentane. The combined organic layers were dried over magnesium sulfate, filtered and concentrated to afford a first portion of the desired crude I1. The acetonitrile layer was distilled off to afford a second portion of desired crude I1. Both crude materials were used directly in the next step without further purification.

[0630] .sup.1H NMR (400 MHz, CDCl.sub.3) δ ppm: 3.79 (s, 3H), 4.11 (m, 2H), 4.27 (s, 2H).

Step 3: Preparation of Methyl (E)-3-(dimethylamino)-2-(2,2,3,3,3-pentafluoropropoxy)prop-2-enoate (Intermediate III2)

[0631] ##STR00051##

[0632] A mixture of methyl 2-(2,2,3,3,3-pentafluoropropoxy)acetate (intermediate 11 prepared as described above) (10.0 g, 45.0 mmol) and 1-tert-butoxy-N,N,N′,N′-tetramethyl-methanediamine (10.2 mL, 49.5 mmol, 1.10 equiv.) was heated up to 60° C. and stirred for 2 hours. After cooling down to room temperature, the reaction mixture was diluted with water and ethyl acetate. The organic layer was washed with saturated sodium hydrogenocarbonate aqueous solution and the aqueous layer was extracted two times with ethyl acetate. The combined organic layers were dried over magnesium sulfate, filtered and concentrated to afford the desired crude I6, which was used directly in the next step without further purification. .sup.1H NMR (400 MHz, CDCl.sub.3) δ ppm: 3.02-3.08 (m, 6H), 3.70 (s, 3H), 4.16-4.24 (m, 2H), 6.85 (s, 1H).

Step 4: Preparation of Methyl 3-oxo-2-(2,2,3,3,3-pentafluoropropoxy)propanoate (Intermediate I7)

[0633] ##STR00052##

[0634] Methyl (E)-3-(dimethylamino)-2-(2,2,3,3,3-pentafluoropropoxy)prop-2-enoate (intermediate 16 prepared as described above) (5.70 g, 21.0 mmol) was dissolved in tetrahydrofuran (40 mL) and 1 M hydrochloric acid (40 mL). The reaction mixture was heated up to 45° C. and stirred for 1.5 hours. After cooling down to room temperature, the reaction mixture was diluted with water and extracted with ethyl acetate. The combined organic layers were washed with water and brine, dried over magnesium sulfate, filtered and concentrated to afford the desired crude I7, which was used directly in the next step without further purification.

Step 5: Preparation of 2-(5-bromo-3-ethylsulfanyl-2-pyridyl)-5-(2,2,3,3,3-pentafluoropropoxy)-1H-pyrimidin-6-one (Intermediate Int-5)

[0635] ##STR00053##

[0636] To a solution of 5-bromo-3-ethylsulfanyl-pyridine-2-carboxamidine (intermediate 15 prepared as described above) (2.60 g, 10.0 mmol) and methyl 3-oxo-2-(2,2,3,3,3-pentafluoropropoxy)propanoate (intermediate 17 prepared as described above) (4.20 g, 17.0 mmol, 1.70 equiv.) in ethanol (80 mL) was added potassium tert-butoxide (2.40 g, 20.0 mmol, 2.00 equiv.). The reaction mixture was heated up to 80° C. and stirred for 30 minutes. After cooling down to room temperature, the reaction mixture was diluted with water and extracted with ethyl acetate. The combined organic layers were washed with water and brine, dried over magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by flash chromatography over silica gel (ethyl acetate in cyclohexane) to afford the desired product as a white/yellow solid. LCMS (method 1): 460/462 (M+H).sup.+ (bromo pattern), Rt 1.13 min. .sup.1H NMR (400 MHz, CDCl.sub.3) δ ppm: 1.43-1.49 (m, 3H), 2.92-2.99 (m, 2H), 4.76 (td, J=12.84, 1.10 Hz, 2H), 7.82 (s, 1H), 7.95 (s, 1H), 8.41 (d, J=2.20 Hz, 1H), 11.15 (br s, 1H).

Step 6: Preparation of 2-(5-bromo-3-ethylsulfanyl-2-pyridyl)-3-methyl-5-(2,2,3,3,3-pentafluoropropoxy)-pyrimidin-4-one (Compound P3)

[0637] ##STR00054##

[0638] A suspension of methyl 4-methylbenzenesulfonate (1.14 mL, 7.57 mmol, 1.10 equiv.), potassium carbonate (1.39 g, 13.8 mmol, 2.00 equiv.) and 2-(5-bromo-3-ethylsulfanyl-2-pyridyl)-5-(2,2,3,3,3-pentafluoropropoxy)-1H-pyrimidin-6-one (intermediate Int-5 prepared as described above) (3.17 g, 6.88 mmol) in acetonitrile (55 mL) was stirred at room temperature overnight. The reaction mixture was directly absorbed on Isolute and purified by flash chromatography over silica gel (ethyl acetate in cyclohexane). The selected fractions were evaporated under reduced pressure and the residue was dissolved in boiling cyclohexane (20 mL). The obtained solution was cooled down to room temperature and the resulting precipitate was filtered to afford the desired product as a light yellow solid. LCMS (method 1): 474/476 (M+H).sup.+ (bromo pattern), Rt 1.09 min. .sup.1H NMR (400 MHz, CDCl.sub.3) δ ppm: 1.32-1.38 (m, 3H), 2.98 (q, J=7.34 Hz, 2H), 3.38 (s, 3H), 4.72 (td, J=12.75, 0.92 Hz, 2H), 7.82-7.84 (m, 1H), 7.86-7.89 (m, 1H), 8.53 (d, J=1.83 Hz, 1H).

Example H4: Preparation of N-[5-ethylsulfanyl-6-[1-methyl-6-oxo-5-(2,2,3,3,3-pentafluoropropoxy)-pyrimidin-2-yl]-3-pyridyl]-N-methyl-acetamide (Compound P4)

[0639] ##STR00055##

[0640] In a microwave vial, to a solution of 2-(5-bromo-3-ethylsulfanyl-2-pyridyl)-3-methyl-5-(2,2,3,3,3-pentafluoropropoxy)pyrimidin-4-one (compound P3 prepared as described above) (0.200 g, 0.422 mmol) in 1,4-dioxane (1.2 mL) were added N-methylacetamide (97.6 μL, 1.27 mmol, 3.00 equiv.), cesium carbonate (0.192 g, 0.591 mmol, 1.40 equiv.) and 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (XantPhos) (34.2 mg, 59.1 μmol, 0.140 equiv.). The vial was purged with argon for 5 minutes and then tris(dibenzylideneacetone)dipalladium(0) (3.86 mg, 4.22 μmol, 0.010 equiv.) was added. The vial was stirred under microwave irradiation at 160° C. for 1 hour. After cooling down to room temperature, the reaction mixture was diluted with dichloromethane and water. The aqueous layer was extracted twice with dichloromethane. The combined organic layers were washed with water and brine, then directly absorbed on Isolute and purified by flash chromatography over silica gel (methanol in dichloromethane) to afford the desired product as a yellow resin. LCMS (method 1): 467 (M+H).sup.+, Rt 0.93 min.

Example H5: Preparation of N-[5-ethylsulfonyl-6-[1-methyl-6-oxo-5-(2,2,3,3,3-pentafluoropropoxy)-pyrimidin-2-yl]-3-pyridyl]-N-methyl-acetamide (Compound P5)

[0641] ##STR00056##

[0642] To a solution of N-[5-ethylsulfanyl-6-[1-methyl-6-oxo-5-(2,2,3,3,3-pentafluoropropoxy)pyrimidin-2-yl]-3-pyridyl]-N-methyl-acetamide (compound P4 prepared as described above) (0.204 g, 0.437 mmol) in dichloromethane (8.2 mL) was added at 0° C. 3-chloroperbenzoic acid (0.189 g, 0.875 mmol, 2.00 equiv.). The reaction mixture was stirred at 0° C. for 30 minutes, then at room temperature for 1 hour. The reaction mixture was then poured on saturated sodium hydrogenocarbonate aqueous solution and dichloromethane was added. The layers were separated, and the organic layer was washed with sodium hydroxide aqueous solution. The aqueous layers were extracted with dichloromethane. The combined organic layers were washed with 40% sodium hydrogen sulfite aqueous solution, dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by flash chromatography over silica gel (methanol in dichloromethane) to afford the desired product as a yellow resin. LCMS (method 1): 499 (M+H).sup.+, Rt 0.88 min. .sup.1H NMR (400 MHz, CDCl.sub.3) δ ppm: 1.31-1.38 (m, 3H), 2.15-2.33 (m, 3H), 3.37 (s, 3H), 3.46-3.54 (m, 5H), 4.75 (t, J=12.84 Hz, 2H), 7.76 (s, 1H), 8.31 (s, 1H), 8.89 (br s, 1H).

Example H6: Preparation of 2-(6-chloro-3-ethylsulfanyl-2-pyridyl)-3-methyl-5-(2,2,3,3,3-pentafluoropropoxy)pyrimidin-4-one (Compound P6)

[0643] ##STR00057##

Step 1: Preparation of 6-chloro-3-ethylsulfanyl-pyridine-2-carboxamidine (Intermediate I8)

[0644] ##STR00058##

[0645] To a suspension of ammonium hydrochloride (4.81 g, 90.0 mmol, 2.50 equiv.) in toluene (72 mL) was added dropwise at 0° C. trimethylaluminium (2 M in toluene, 40.0 mL, 79.2 mmol, 2.20 equiv.). The reaction mixture was allowed to reach room temperature and stirring was continued until no more gas was evolved. Then a solution of 6-chloro-3-ethylsulfanyl-pyridine-2-carbonitrile (CAS 102645-27-2) (7.15 g, 36.0 mmol) in toluene (11 mL) was added to the reaction mixture. It was heated up to 90° C. and stirred overnight. After cooling down to 0° C., methanol (70 mL) was added portionwise, followed by a mixture of methanol:water (56 mL, 4:1). It was then stirred at room temperature for 1 hour. The resulting suspension was filtered and the filtrate was concentrated to afford the desired crude amidine 18, which was used directly in the next step without further purification. LCMS (method 1): 216/218 (M+H).sup.+, Rt 0.22 min.

Step 2: Preparation of 2-(6-chloro-3-ethylsulfanyl-2-pyridyl)-5-(2,2,3,3,3-pentafluoropropoxy)-1H-pyrimidin-6-one (Intermediate Int-2)

[0646] ##STR00059##

[0647] To a solution of 6-chloro-3-ethylsulfanyl-pyridine-2-carboxamidine (intermediate 18 prepared as described above) (1.25 g, 5.80 mmol) and methyl 3-oxo-2-(2,2,3,3,3-pentafluoropropoxy)propanoate (intermediate I7 prepared as described above) (2.90 g, 11.6 mmol, 2.00 equiv.) in ethanol (30 mL) was added potassium tert-butoxide (1.37 g, 11.6 mmol, 2.00 equiv.). The reaction mixture was heated up to 80° C. and stirred for 30 minutes. After cooling down to room temperature, the reaction mixture was diluted with water and extracted with ethyl acetate. The combined organic layers were washed with water and brine, dried over magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by flash chromatography over silica gel (ethyl acetate in cyclohexane) to afford the desired product as a white/yellow solid. LCMS (method 1): 416/418 (M+H).sup.+, Rt 1.08 min. .sup.1H NMR (400 MHz, CDCl.sub.3) δ ppm: 1.41-1.46 (m, 3H), 2.96 (q, J=7.34 Hz, 2H), 4.76 (td, J=12.93, 0.92 Hz, 2H), 7.38 (d, J=8.44 Hz, 1H), 7.69 (d, J=8.44 Hz, 1H), 7.95 (s, 1H), 11.11 (br s, 1H).

Step 3: Preparation of 2-(6-chloro-3-ethylsulfanyl-2-pyridyl)-3-methyl-5-(2,2,3,3,3-pentafluoropropoxy)-pyrimidin-4-one (Compound P6)

[0648] ##STR00060##

[0649] A suspension of methyl 4-methylbenzenesulfonate (0.566 mL, 3.75 mmol, 1.10 equiv.), potassium carbonate (0.689 g, 6.82 mmol, 2.00 equiv.) and 2-(6-chloro-3-ethylsulfanyl-2-pyridyl)-5-(2,2,3,3,3-pentafluoropropoxy)-1H-pyrimidin-6-one (intermediate Int-2 prepared as described above) (1.42 g, 3.41 mmol) in acetonitrile (27 mL) was heated up to 50° C. and stirred for 1.5 hours. The reaction mixture was directly adsorbed on Isolute and purified by flash chromatography over silica gel (ethyl acetate in cyclohexane) to afford the desired product. LCMS (method 1): 430/432 (M+H).sup.+, Rt 1.06 min.

Example H7: Preparation of 2-(6-chloro-3-ethylsulfonyl-2-pyridyl)-3-methyl-5-(2,2,3,3,3-pentafluoropropoxy)pyrimidin-4-one (Compound P7)

[0650] ##STR00061##

[0651] To a solution of 2-(6-chloro-3-ethylsulfanyl-2-pyridyl)-3-methyl-5-(2,2,3,3,3-pentafluoropropoxy)pyrimidin-4-one (compound P6 prepared as described above) (1.35 g, 3.14 mmol) in dichloromethane (54 mL) was added at 0° C. 3-chloroperbenzoic acid (1.41 g, 6.27 mmol, 2.00 equiv.). The reaction mixture was stirred at 0° C. for 30 minutes, then at room temperature overnight. The reaction mixture was then poured on saturated sodium hydrogen carbonate aqueous solution and dichloromethane was added. The layers were separated and the organic layer was washed with sodium hydroxide aqueous solution. The aqueous layers were extracted with dichloromethane. The combined organic layers were washed with 40% sodium hydrogen sulfite aqueous solution, dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by flash chromatography over silica gel (methanol in dichloromethane) to afford the desired product as a colorless oil. LCMS (method 1): 462/464 (M+H).sup.+, Rt 1.00 min. .sup.1H NMR (400 MHz, CDCl.sub.3) δ ppm: 1.33 (t, J=7.52 Hz, 3H), 3.37 (s, 3H), 3.41-3.51 (m, 2H), 4.74 (td, J=12.84, 1.10 Hz, 2H), 7.70 (d, J=8.44 Hz, 1H), 7.75 (s, 1H), 8.34-8.40 (m, 1H).

Example H8: Preparation of 2-[3-ethylsulfonyl-6-(methylamino)-2-pyridyl]-3-methyl-5-(2,2,3,3,3-penta-fluoropropoxy)pyrimidin-4-one (Compound P8)

[0652] ##STR00062##

[0653] To a solution of 2-(6-chloro-3-ethylsulfonyl-2-pyridyl)-3-methyl-5-(2,2,3,3,3-pentafluoropropoxy)-pyrimidin-4-one (compound P7 prepared as described above) (0.564 g, 1.22 mmol) in tetrahydrofuran (2 mL) was added at room temperature methylamine (2 M in tetrahydrofuran, 3.05 mL, 6.11 mmol, 5.00 equiv.). The reaction mixture was stirred under microwave irradiation at 120° C. for 30 minutes. After cooling down to room temperature, the reaction mixture was directly adsorbed on Isolute and purified by flash chromatography over silica gel (ethyl acetate in cyclohexane) to afford the desired product.

[0654] LCMS (method 1): 457 (M+H).sup.+, Rt 0.92 min.

Example H9: Preparation of N-[5-ethylsulfonyl-6-[1-methyl-6-oxo-5-(2,2,3,3,3-pentafluoropropoxy)-pyrimidin-2-yl]-2-pyridyl]-N-methyl-acetamide (Compound P9)

[0655] ##STR00063##

[0656] To a solution of 2-[3-ethylsulfonyl-6-(methylamino)-2-pyridyl]-3-methyl-5-(2,2,3,3,3-pentafluoropropoxy)pyrimidin-4-one (compound P8 prepared as described above) (35 mg, 0.077 mmol) in dichloromethane (2 mL) were added acetyl chloride (5.5 μL, 0.077 mmol, 1.0 equiv.) and N,N-diethylethanamine (12 μL, 0.084 mmol, 1.1 equiv.). The reaction mixture was stirred at room temperature for 40 minutes. Additional acetyl chloride (5.5 μL) and N,N-diethylethanamine (12 μL) were added again and it was stirred for 2 more hours. Catalytic amount of 4-dimethylaminopyridine was added and it was stirred at 45° C. overnight. Additional acetyl chloride (5.5 μL) and N,N-diethylethanamine (12 μL) were added again, before the mixture was concentrated. Pyridine (3 mL) was added to the residue, as well as additional acetyl chloride (2×5.5 μL) and it was stirred at 60° C. until full conversion was reached. After cooling down to room temperature, the reaction mixture was diluted with water and extracted with dichloromethane. The combined organic layers were washed with water and brine, dried over magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified first by flash chromatography over silica gel (ethyl acetate in cyclohexane), then by reverse phase chromatography to afford the desired product as a red resin. LCMS (method 1): 499 (M+H).sup.+, Rt 0.93 min. .sup.1H NMR (400 MHz, CDCl.sub.3) δ ppm: 1.26-1.36 (m, 3H), 2.42 (s, 3H), 3.34-3.36 (m, 3H), 3.38-3.45 (m, 2H), 3.53 (s, 3H), 4.75 (br t, J=12.84 Hz, 2H), 7.76 (s, 1H), 8.24-8.35 (m, 2H).

Example H10: Preparation of 1-[5-ethylsulfanyl-6-[1-methyl-6-oxo-5 (2,2,3,3,3pentafluoropropoxy) pyrimidin-2-yl]-3-pyridyl]cyclopropanecarbonitrile (Compound P10)

[0657] ##STR00064##

Step 1: Preparation of Ethyl 2-cyano-2-[5-ethylsulfanyl-6-[1-methyl-6-oxo-5-(2,2,3,3,3-pentafluoro-Propoxy)pyrimidin-2-yl]-3-pyridyl]acetate (Intermediate Int-4)

[0658] ##STR00065##

[0659] To a solution of 2-(5-bromo-3-ethylsulfanyl-2-pyridyl)-3-methyl-5-(2,2,3,3,3-pentafluoropropoxy)pyrimidin-4-one (compound P3 prepared as described above) (0.460 g, 0.970 mmol) in dimethyl sulfoxide (2.91 mL) were added ethyl 2-cyanoacetate (0.518 mL, 4.85 mmol, 5.00 eq.), L-proline (0.0226 g, 0.194 mmol, 0.20 eq.), potassium carbonate (1.34 g, 9.70 mmol, 10.0 eq.) and copper(I) iodide (0.0185 g, 0.0970 mmol, 0.10 eq.) at room temperature under Argon. The reaction mixture was stirred at 140° C. for 1 h. After cooling down to 0° C., HCl (1 N, 12.0 mL) was added dropwise very slowly due to strong foaming and the mixture was extracted with ethyl acetate. The combined organic layers were washed with water and brine, dried over magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by flash chromatography over silica gel (ethyl acetate in cyclohexane) to afford the desired product as brown oil. LCMS (method 1): 507 (M+H).sup.+, Rt 1.05 min.

Step 2: Preparation of 2-[5-ethylsulfanyl-6-[1-methyl-6-oxo-5-(2,2,3,3,3-pentafluoropropoxy)pyrimidin-2-yl]-3-pyridyl]acetonitrile (Intermediate Int-3)

[0660] ##STR00066##

[0661] To a solution of ethyl 2-cyano-2-[5-ethylsulfanyl-6-[1-methyl-6-oxo-5-(2,2,3,3,3-pentafluoropropoxy)-pyrimidin-2-yl]-3-pyridyl]acetate (intermediate Int-4 prepared as described above) (0.238 g, 0.470 mmol) in dimethyl sulfoxide (5.00 mL) and water (3.00 mL) was added sodium chloride (0.277 g, 4.70 mmol, 10.0 eq.) at room temperature. The reaction mixture was stirred at 120° C. for 4.5 h, adding more sodium chloride from time to time. Then it was cooled down to room temperature and stirred over night. Additional sodium chloride was added, it was heated up again to 140° C. and stirred for 6 h. After cooling down to room temperature, the reaction mixture was diluted with water and extracted with ethyl acetate. The combined organic layers were washed with water and brine, dried over magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by flash chromatography over silica gel (ethyl acetate in cyclohexane) to afford the desired product as light brown resin. LCMS (method 1): 435 (M+H).sup.+, Rt 0.96 min. .sup.1H NMR (400 MHz, CDCl.sub.3) δ ppm: 1.35 (t, 3H), 3.01 (q, 2H), 3.39 (s, 3H), 3.89 (s, 2H), 4.69-4.77 (t, 2H), 7.79 (d, 1H), 7.88 (s, 1H), 8.43 (d, 1H).

Step 3: Preparation of 1-[5-ethylsulfanyl-6-[1-methyl-6-oxo-5 (2,2,3,3,3pentafluoropropoxy) pyrimidin-2-yl]-3-pyridyl]cyclopropanecarbonitrile (Compound P10)

[0662] ##STR00067##

[0663] To a solution of 2-[5-ethylsulfanyl-6-[1-methyl-6-oxo-5-(2,2,3,3,3-pentafluoropropoxy)pyrimidin-2-yl]-3-pyridyl]acetonitrile (intermediate Int-3 prepared as described above) (0.158 g, 0.364 mmol) in acetonitrile (1.09 mL) was added cesium carbonate (0.356 g, 1.09 mmol, 3.00 eq.) followed by dropwise addition of 1,2-dibromoethane (0.0642 mL, 0.727 mmol, 2.00 eq.) at room temperature. The reaction mixture was stirred at 80° C. for 24 h. After cooling down to room temperature, the reaction mixture was diluted with water and extracted with ethyl acetate. The combined organic layers were dried over magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by flash chromatography over silica gel (ethyl acetate in cyclohexane) to afford the desired product as a colorless oil. LCMS (method 1): 461 (M+H).sup.+, Rt 1.02 min. .sup.1H NMR (400 MHz, CDCl.sub.3) δ ppm: 1.35 (t, 3H), 1.58 (m, 2H), 1.92 (m, 2H), 2.95-3.03 (m, 2H), 3.38 (s, 3H), 4.69-4.77 (t, 2H), 7.76 (d, 1H), 7.82 (s, 1H), 8.31 (d, 1H).

Example H11: Preparation of 1-[5-ethylsulfonyl-6-[1-methyl-6-oxo-5-(2,2,3,3,3-pentafluoropropoxy)-pyrimidin-2-yl]-3-pyridyl]cyclopropanecarbonitrile (Compound P11)

[0664] ##STR00068##

[0665] To a solution of 1-[5-ethylsulfanyl-6-[1-methyl-6-oxo-5 (2,2,3,3,3pentafluoropropoxy) pyrimidin-2-yl]-3-pyridyl]cyclopropanecarbonitrile (compound P10 prepared as described above) (0.0310 g, 0.0673 mmol) in dichloromethane (1.24 mL) was added mCPBA (0.0302 g, 0.135 mmol, 2.00 eq.) at 0° C. The reaction mixture was stirred at room temperature for 15 min and was poured into sat. aq. sodium bicarbonate solution. The mixture was extracted with dichloromethane, the organic phase was separated and washed with a solution of sodium hydroxide. The aqueous layer was extracted once again with dichloromethane and the combined organic layers were washed with a 40% sodium bisulfite solution. Afterwards the organic layer was dried over sodium sulfate, filtered and concentrated under reduced pressure after checking the presence of peroxides with a starch paper test. The reside was purified by flash chromatography over silica gel (ethyl acetate in cyclohexane) to afford the desired product as light yellow solid. LCMS (method 1): 493 (M+H).sup.+, Rt 0.96 min. .sup.1H NMR (400 MHz, CDCl.sub.3) δ ppm: 1.35 (t, 3H), 1.65 (m, 2H), 2.02 (m, 2H), 3.32 (s, 3H), 3.45-3.53 (q, 2H), 4.70-4.79 (t, 2H), 7.76 (d, 1H), 8.20 (s, 1H), 8.95 (d, 1H).

Example H12: Preparation of 2-[3-ethylsulfanyl-5-(2-pyridyloxy)-2-pyridyl]-3-methyl-5-(2,2,3,3,3-pentafluoropropoxy)pyrimidin-4-one (Compound P19)

[0666] ##STR00069##

Step 1: Preparation of 2-(3-ethylsulfanyl-5-hydroxy-2-pyridyl)-3-methyl-5-(2,2,3,3,3-pentafluoro-propoxy)pyrimidin-4-one (Intermediate Int-1)

[0667] ##STR00070##

[0668] A mixture of 2-(5-bromo-3-ethylsulfanyl-2-pyridyl)-3-methyl-5-(2,2,3,3,3-pentafluoropropoxy)pyrimidin-4-one (compound P3 prepared as described above) (100 mg, 0.211 mmol), cesium carbonate (2.0 eq., 0.422 mmol) and (E)-benzaldehyde oxime (1.0 eq., 0.211 mmol) in N,N-dimethylformamide (2 mL/mmol) was heated to 50° C. overnight, then at 85° C. for three days. A further amount of (E)-benzaldehyde oxime (0.5 eq.) was added during this extended heating time. The reaction mixture was diluted with dichloromethane, water and aqueous sodium hydrogen carbonate. The separated aqueous layer was acidified to pH 5 and extracted with dichloromethane (3×). The combined organic phases were dried over sodium sulfate, filtered and concentrated. The residue was purified by flash chromatography on silica gel (ethyl acetate gradient in cyclohexane) to afford 2-(3-ethylsulfanyl-5-hydroxy-2-pyridyl)-3-methyl-5-(2,2,3,3,3-pentafluoro-propoxy)pyrimidin-4-one. LCMS (method 1): 412 (M+H).sup.+, Rt 0.92 min.

Step 2: Preparation of 2-[3-ethylsulfanyl-5-(2-pyridyloxy)-2-pyridyl]-3-methyl-5-(2,2,3,3,3-pentafluoropropoxy)pyrimidin-4-one (Compound P19)

[0669] ##STR00071##

[0670] A mixture of 2-(3-ethylsulfanyl-5-hydroxy-2-pyridyl)-3-methyl-5-(2,2,3,3,3-pentafluororopoxy)pyrimidin-4-one (intermediate Int-1 prepared as described above) (38 mg, 0.092 mmol), potassium carbonate (2 eq., 0.185 mmol), 2-iodopyridine (1.3 eq., 0.120 mmol), sodium iodide (0.1 eq., 0.0092 mmol) and copper iodide (0.1 eq., 0.0092 mmol) in N,N-dimethylformamide (4 mL) was stirred at 100° C. overnight, then at 120° C. for 3 hours and at 143° C. for one hour. The reaction mixture was diluted with ethyl acetate and water, the aqueous layer extracted with ethyl acetate (3×), the combined organic layers washed with water and brine, dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified by flash chromatography on silica gel (ethyl acetate gradient in cyclohexane) to afford 2-[3-ethylsulfanyl-5-(2-pyridyloxy)-2-pyridyl]-3-methyl-5-(2,2,3,3,3-pentafluoropropoxy)pyrimidin-4-one (compound P19). LCMS (method 1): 489 (M+H).sup.+, Rt 1.06 min.

TABLE-US-00013 TABLE P Examples of compounds of formula (I) LCMS R.sub.t [M + H].sup.+ Mp No. IUPAC name Structures (min) (measured) Method (° C.) P1 2-(3-ethylsulfanyl-2- pyridyl)-3-methyl-5- (2,2,3,3,3- pentafluoropropoxy) pyrimidin-4-one [00072] 0.97 396 1 — P2 2-(3-ethylsulfonyl-2- pyridyl)-3-methyl-5- (2,2,3,3,3- pentafluoropropoxy) pyrimidin-4-one [00073] 0.89 428 1 107-118 P3 2-(5-bromo-3- ethylsulfanyl-2- pyridyl)-3-methyl- 5-(2,2,3,3,3- pentafluoropropoxy) pyrimidin-4-one [00074] 1.09 474/476 1 — P4 N-[5-ethylsulfanyl- 6-[1-methyl-6-oxo- 5-(2,2,3,3,3- pentafluoropropoxy) pyrimidin-2-yl]-3- pyridyl]-N- methyl-acetamide [00075] 0.93 467 1 — P5 N-[5-ethylsulfonyl- 6-[1-methyl-6-oxo- 5-(2,2,3,3,3- pentafluoropropoxy) pyrimidin-2-yl]-3- pyridyl]-N- methyl-acetamide [00076] 0.88 499 1 — P6 2-(6-chloro-3- ethylsulfanyl-2- pyridyl)-3-methyl- 5-(2,2,3,3,3- pentafluoropropoxy) pyrimidin-4-one [00077] 1.06 430/432 1 — P7 2-(6-chloro-3- ethylsulfonyl- 2-pyridyl)-3- methyl-5- (2,2,3,3,3- pentafluoropropoxy) pyrimidin-4-one [00078] 1.00 462/464 1 — P8 2-[3-ethylsulfonyl- 6-(methylamino)- 2-pyridyl]-3- methyl-5- (2,2,3,3,3- pentafluoropropoxy) pyrimidin-4-one [00079] 0.92 457 1 — P9 N-[5-ethylsulfonyl- 6-[1-methyl-6- oxo-5-(2,2,3,3,3- pentafluoropropoxy) pyrimidin-2-yl]-2- pyridyl]-N- methyl-acetamide [00080] 0.93 499 1 — P10 1-[5-ethylsulfanyl- 6-[1-methyl-6-oxo- 5-(2,2,3,3,3- pentafluoropropoxy) pyrimidin-2-yl]-3- pyridyl]cyclo- propanecarbonitrile [00081] 1.02 461 1 — P11 1-[5-ethylsulfonyl- 6-[1-methyl-6-oxo- 5-(2,2,3,3,3- pentafluoropropoxy) pyrimidin-2-yl]-3- pyridyl]cyclo- propanecarbonitrile [00082] 0.96 493 2 — P12 2-[5-ethylsulfanyl- 6-[1-methyl-6-oxo- 5-(2,2,3,3,3- pentafluoropropoxy) pyrimidin-2-yl]-3- pyridyl]-2- methyl-propanenitrile [00083] 1.04 463 1 — P13 2-[5-ethylsulfonyl- 6-[1-methyl-6-oxo- 5-(2,2,3,3,3- pentafluoropropoxy) pyrimidin-2-yl]-3- pyridyl]-2-methyl- propanenitrile [00084] 0.99 495 1 — P14 2-[3-ethylsulfonyl- 6-(1,2,4-triazol-1- yl)-2-pyridyl]-3- methyl-5-(2,2,3,3,3- pentafluoropropoxy) pyrimidin-4-one [00085] 0.92 495 1 — P15 1-[5-ethylsulfonyl- 6-[1-methyl-6-oxo- 5-(2,2,3,3,3- pentafluoropropoxy) pyrimidin-2-yl]-2- pyridyl]-1,3- dimethyl-urea [00086] 0.90 514 1 — P16 N-[5-ethylsulfonyl- 6-[1-methyl-6-oxo- 5-(2,2,3,3,3- pentafluoropropoxy) pyrimidin-2-yl]-2- pyridyl]-N- methyl-cyclo- propanecarboxamide [00087] 1.00 525 1 — P17 2-(5-cyclopropyl- 3-ethylsulfanyl- 2-pyridyl)-3- methyl-5-(2,2,3,3,3- pentafluoropropoxy) pyrimidin-4-one [00088] 1.09 436 1 — P18 2-(5-cyclopropyl-3- ethylsulfonyl-2- pyridyl)-3- methyl-5-(2,2,3,3,3- pentafluoropropoxy) pyrimidin-4-one [00089] 1.01 468 1 134-141 P19 2-[3-ethylsulfanyl- 5-(2-pyridyloxy)- 2-pyridyl]-3- methyl-5-(2,2,3,3,3- pentafluoropropoxy) pyrimidin-4-one [00090] 1.06 489 1 — P20 2-[3-ethylsulfonyl- 5-(2-pyridyloxy)- 2-pyridyl]-3- methyl-5-(2,2,3,3,3- pentafluoropropoxy) pyrimidin-4-one [00091] 1.05 521 1 —

TABLE-US-00014 TABLE Int Examples of intermediates LCMS R.sub.t [M + H].sup.+ Me- Mp No. IUPAC name Structures (min) (measured) thod (° C.) Int-1 2-(3-ethylsulfanyl- 5-hydroxy-2- pyridyl)-3- methyl-5-(2,2,3,3,3- pentafluoropropoxy) pyrimidin-4-one [00092] 0.92 412 1 — Int-2 2-(6-chloro-3- ethylsulfanyl-2- pyridyl)-5- (2,2,3,3,3- pentafluoro- propoxy)-1H- pyrimidin-6-one [00093] 1.08 416/418 1 — Int-3 2-[5-ethylsulfanyl- 6-[1-methyl-6-oxo- 5-(2,2,3,3,3- pentafluoropropoxy) pyrimidin-2-yl]-3- pyridyl]acetonitrile [00094] 0.96 435 1 — Int-4 ethyl 2-cyano-2- [5-ethylsulfanyl- 6-[1-methyl-6- oxo-5-(2,2,3,3,3- pentafluoropropoxy) pyrimidin-2-yl]-3- pyridyl]acetate [00095] 1.05 507 1 — Int-5 2-(5-bromo-3- ethylsulfanyl-2- pyridyl)-5- (2,2,3,3,3- pentafluoro- propoxy)-1H- pyrimidin-6-one. [00096] 1.13 460/462 1 —

[0671] 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.

[0672] 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-81 and Tables B-1 to B-54 and Table P of the present invention”):

[0673] an adjuvant selected from the group of substances consisting of petroleum oils (alternative name) (628)+TX,

[0674] an adjuvant selected from the group of substances consisting of petroleum oils (alternative name) (628)+TX,

[0675] 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, bromocyclen (918)+TX, bromophos (920)+TX, bromophos-ethyl (921)+TX, bromopropylate (94)+TX, buprofezin (99)+TX, butocarboxim (103)+TX, butoxycarboxim (104)+TX, butylpyridaben (alternative name)+TX, calcium polysulfide (IUPAC name) (111)+TX, camphechlor (941)+TX, carbanolate (943)+TX, carbaryl (115)+TX, carbofuran (118)+TX, carbophenothion (947)+TX, CGA 50′439 (development code) (125)+TX, chinomethionat (126)+TX, chlorbenside (959)+TX, chlordimeform (964)+TX, chlordimeform hydrochloride (964)+TX, chlorfenapyr (130)+TX, chlorfenethol (968)+TX, chlorfenson (970)+TX, chlorfensulfide (971)+TX, chlorfenvinphos (131)+TX, chlorobenzilate (975)+TX, chloromebuform (977)+TX, chloromethiuron (978)+TX, chloropropylate (983)+TX, chlorpyrifos (145)+TX, chlorpyrifos-methyl (146)+TX, chlorthiophos (994)+TX, cinerin I (696)+TX, cinerin II (696)+TX, cinerins (696)+TX, clofentezine (158)+TX, closantel (alternative name) [CCN]+TX, coumaphos (174)+TX, crotamiton (alternative name) [CCN]+TX, crotoxyphos (1010)+TX, cufraneb (1013)+TX, cyanthoate (1020)+TX, cyflumetofen (CAS Reg. No.: 400882-07-7)+TX, cyhalothrin (196)+TX, cyhexatin (199)+TX, 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, dialifos (1042)+TX, diazinon (227)+TX, dichlofluanid (230)+TX, dichlorvos (236)+TX, dicliphos (alternative name)+TX, dicofol (242)+TX, dicrotophos (243)+TX, dienochlor (1071)+TX, dimefox (1081)+TX, dimethoate (262)+TX, dinactin (alternative name) (653)+TX, dinex (1089)+TX, dinex-diclexine (1089)+TX, dinobuton (269)+TX, dinocap (270)+TX, dinocap-4 [CCN]+TX, dinocap-6 [CCN]+TX, dinocton (1090)+TX, dinopenton (1092)+TX, dinosulfon (1097)+TX, dinoterbon (1098)+TX, dioxathion (1102)+TX, diphenyl sulfone (IUPAC name) (1103)+TX, disulfiram (alternative name) [CCN]+TX, disulfoton (278)+TX, DNOC (282)+TX, dofenapyn (1113)+TX, doramectin (alternative name) [CCN]+TX, endosulfan (294)+TX, endothion (1121)+TX, EPN (297)+TX, eprinomectin (alternative name) [CCN]+TX, ethion (309)+TX, ethoate-methyl (1134)+TX, etoxazole (320)+TX, etrimfos (1142)+TX, fenazaflor (1147)+TX, fenazaquin (328)+TX, fenbutatin oxide (330)+TX, fenothiocarb (337)+TX, fenpropathrin (342)+TX, fenpyrad (alternative name)+TX, fenpyroximate (345)+TX, fenson (1157)+TX, fentrifanil (1161)+TX, fenvalerate (349)+TX, fipronil (354)+TX, fluacrypyrim (360)+TX, fluazuron (1166)+TX, flubenzimine (1167)+TX, flucycloxuron (366)+TX, flucythrinate (367)+TX, fluenetil (1169)+TX, flufenoxuron (370)+TX, flumethrin (372)+TX, fluorbenside (1174)+TX, fluvalinate (1184)+TX, FMC 1137 (development code) (1185)+TX, formetanate (405)+TX, formetanate hydrochloride (405)+TX, formothion (1192)+TX, formparanate (1193)+TX, gamma-HCH (430)+TX, glyodin (1205)+TX, halfenprox (424)+TX, heptenophos (432)+TX, hexadecyl cyclopropanecarboxylate (IUPAC/Chemical Abstracts name) (1216)+TX, hexythiazox (441)+TX, iodomethane (IUPAC name) (542)+TX, isocarbophos (alternative name) (473)+TX, isopropyl O-(methoxyaminothiophosphoryl)salicylate (IUPAC name) (473)+TX, ivermectin (alternative name) [CCN]+TX, jasmolin I (696)+TX, jasmolin II (696)+TX, jodfenphos (1248)+TX, lindane (430)+TX, lufenuron (490)+TX, malathion (492)+TX, malonoben (1254)+TX, mecarbam (502)+TX, mephosfolan (1261)+TX, mesulfen (alternative name) [CCN]+TX, methacrifos (1266)+TX, methamidophos (527)+TX, methidathion (529)+TX, methiocarb (530)+TX, methomyl (531)+TX, methyl bromide (537)+TX, metolcarb (550)+TX, mevinphos (556)+TX, mexacarbate (1290)+TX, milbemectin (557)+TX, milbemycin oxime (alternative name) [CCN]+TX, mipafox (1293)+TX, monocrotophos (561)+TX, morphothion (1300)+TX, moxidectin (alternative name) [CCN]+TX, naled (567)+TX, NC-184 (compound code)+TX, NC-512 (compound code)+TX, nifluridide (1309)+TX, nikkomycins (alternative name) [CCN]+TX, nitrilacarb (1313)+TX, nitrilacarb 1:1 zinc chloride complex (1313)+TX, NNI-0101 (compound code)+TX, NNI-0250 (compound code)+TX, omethoate (594)+TX, oxamyl (602)+TX, oxydeprofos (1324)+TX, oxydisulfoton (1325)+TX, pp′-DDT (219)+TX, parathion (615)+TX, permethrin (626)+TX, petroleum oils (alternative name) (628)+TX, phenkapton (1330)+TX, phenthoate (631)+TX, phorate (636)+TX, phosalone (637)+TX, phosfolan (1338)+TX, phosmet (638)+TX, phosphamidon (639)+TX, phoxim (642)+TX, pirimiphos-methyl (652)+TX, polychloroterpenes (traditional name) (1347)+TX, polynactins (alternative name) (653)+TX, proclonol (1350)+TX, profenofos (662)+TX, promacyl (1354)+TX, propargite (671)+TX, propetamphos (673)+TX, propoxur (678)+TX, prothidathion (1360)+TX, prothoate (1362)+TX, pyrethrin I (696)+TX, pyrethrin II (696)+TX, pyrethrins (696)+TX, pyridaben (699)+TX, pyridaphenthion (701)+TX, pyrimidifen (706)+TX, pyrimitate (1370)+TX, quinalphos (711)+TX, quintiofos (1381)+TX, R-1492 (development code) (1382)+TX, RA-17 (development code) (1383)+TX, rotenone (722)+TX, schradan (1389)+TX, sebufos (alternative name)+TX, selamectin (alternative name) [CCN]+TX, SI-0009 (compound code)+TX, sophamide (1402)+TX, spirodiclofen (738)+TX, spiromesifen (739)+TX, SSI-121 (development code) (1404)+TX, sulfiram (alternative name) [CCN]+TX, sulfluramid (750)+TX, sulfotep (753)+TX, sulfur (754)+TX, SZI-121 (development code) (757)+TX, tau-fluvalinate (398)+TX, tebufenpyrad (763)+TX, TEPP (1417)+TX, terbam (alternative name)+TX, tetrachlorvinphos (777)+TX, tetradifon (786)+TX, tetranactin (alternative name) (653)+TX, tetrasul (1425)+TX, thiafenox (alternative name)+TX, thiocarboxime (1431)+TX, thiofanox (800)+TX, thiometon (801)+TX, thioquinox (1436)+TX, thuringiensin (alternative name) [CCN]+TX, triamiphos (1441)+TX, triarathene (1443)+TX, triazophos (820)+TX, triazuron (alternative name)+TX, trichlorfon (824)+TX, trifenofos (1455)+TX, trinactin (alternative name) (653)+TX, vamidothion (847)+TX, vaniliprole [CCN] and YI-5302 (compound code)+TX,

[0676] 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,

[0677] 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,

[0678] 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,

[0679] 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,

[0680] 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, a soil sterilant selected from the group of substances consisting of iodomethane (IUPAC name) (542) and methyl bromide (537)+TX,

[0681] 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,

[0682] 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,

[0683] 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, dimpropyridaz+TX, dialifos (1042)+TX, diamidafos (1044)+TX, diazinon (227)+TX, dicapthon (1050)+TX, dichlofenthion (1051)+TX, dichlorvos (236)+TX, dicliphos (alternative name)+TX, dicresyl (alternative name) [CCN]+TX, dicrotophos (243)+TX, dicyclanil (244)+TX, dieldrin (1070)+TX, diethyl 5-methylpyrazol-3-yl phosphate (IUPAC name) (1076)+TX, diflubenzuron (250)+TX, dilor (alternative name) [CCN]+TX, dimefluthrin [CCN]+TX, dimefox (1081)+TX, dimetan (1085)+TX, dimethoate (262)+TX, dimethrin (1083)+TX, dimethylvinphos (265)+TX, dimetilan (1086)+TX, dinex (1089)+TX, dinex-diclexine (1089)+TX, dinoprop (1093)+TX, dinosam (1094)+TX, dinoseb (1095)+TX, dinotefuran (271)+TX, diofenolan (1099)+TX, dioxabenzofos (1100)+TX, dioxacarb (1101)+TX, dioxathion (1102)+TX, disulfoton (278)+TX, dithicrofos (1108)+TX, DNOC (282)+TX, doramectin (alternative name) [CCN]+TX, DSP (1115)+TX, ecdysterone (alternative name) [CCN]+TX, EI 1642 (development code) (1118)+TX, emamectin (291)+TX, emamectin benzoate (291)+TX, EMPC (1120)+TX, empenthrin (292)+TX, endosulfan (294)+TX, endothion (1121)+TX, endrin (1122)+TX, EPBP (1123)+TX, EPN (297)+TX, epofenonane (1124)+TX, eprinomectin (alternative name) [CCN]+TX, esfenvalerate (302)+TX, etaphos (alternative name) [CCN]+TX, ethiofencarb (308)+TX, ethion (309)+TX, ethiprole (310)+TX, ethoate-methyl (1134)+TX, ethoprophos (312)+TX, ethyl formate (IUPAC name) [CCN]+TX, ethyl-DDD (alternative name) (1056)+TX, ethylene dibromide (316)+TX, ethylene dichloride (chemical name) (1136)+TX, ethylene oxide [CCN]+TX, etofenprox (319)+TX, etrimfos (1142)+TX, EXD (1143)+TX, famphur (323)+TX, fenamiphos (326)+TX, fenazaflor (1147)+TX, fenchlorphos (1148)+TX, fenethacarb (1149)+TX, fenfluthrin (1150)+TX, fenitrothion (335)+TX, fenobucarb (336)+TX, fenoxacrim (1153)+TX, fenoxycarb (340)+TX, fenpirithrin (1155)+TX, fenpropathrin (342)+TX, fenpyrad (alternative name)+TX, fensulfothion (1158)+TX, fenthion (346)+TX, fenthion-ethyl [CCN]+TX, fenvalerate (349)+TX, fipronil (354)+TX, flonicamid (358)+TX, flubendiamide (CAS. Reg. No.: 272451-65-7)+TX, flucofuron (1168)+TX, flucycloxuron (366)+TX, flucythrinate (367)+TX, fluenetil (1169)+TX, flufenerim [CCN]+TX, flufenoxuron (370)+TX, flufenprox (1171)+TX, flumethrin (372)+TX, fluvalinate (1184)+TX, FMC 1137 (development code) (1185)+TX, fonofos (1191)+TX, formetanate (405)+TX, formetanate hydrochloride (405)+TX, formothion (1192)+TX, formparanate (1193)+TX, fosmethilan (1194)+TX, fospirate (1195)+TX, fosthiazate (408)+TX, fosthietan (1196)+TX, furathiocarb (412)+TX, furethrin (1200)+TX, gamma-cyhalothrin (197)+TX, gamma-HCH (430)+TX, guazatine (422)+TX, guazatine acetates (422)+TX, GY-81 (development code) (423)+TX, halfenprox (424)+TX, halofenozide (425)+TX, HCH (430)+TX, HEOD (1070)+TX, heptachlor (1211)+TX, heptenophos (432)+TX, heterophos [CCN]+TX, hexaflumuron (439)+TX, HHDN (864)+TX, hydramethylnon (443)+TX, hydrogen cyanide (444)+TX, hydroprene (445)+TX, hyquincarb (1223)+TX, imidacloprid (458)+TX, imiprothrin (460)+TX, indoxacarb (465)+TX, iodomethane (IUPAC name) (542)+TX, IPSP (1229)+TX, isazofos (1231)+TX, isobenzan (1232)+TX, isocarbophos (alternative name) (473)+TX, isodrin (1235)+TX, isofenphos (1236)+TX, isolane (1237)+TX, isoprocarb (472)+TX, isopropyl O-(methoxyaminothiophosphoryl)salicylate (IUPAC name) (473)+TX, isoprothiolane (474)+TX, isothioate (1244)+TX, isoxathion (480)+TX, ivermectin (alternative name) [CCN]+TX, jasmolin 1 (696)+TX, jasmolin II (696)+TX, jodfenphos (1248)+TX, juvenile hormone I (alternative name) [CCN]+TX, juvenile hormone II (alternative name) [CCN]+TX, juvenile hormone III (alternative name) [CCN]+TX, kelevan (1249)+TX, kinoprene (484)+TX, lambda-cyhalothrin (198)+TX, lead arsenate [CCN]+TX, lepimectin (CCN)+TX, leptophos (1250)+TX, lindane (430)+TX, lirimfos (1251)+TX, lufenuron (490)+TX, lythidathion (1253)+TX, m-cumenyl methylcarbamate (IUPAC name) (1014)+TX, magnesium phosphide (IUPAC name) (640)+TX, malathion (492)+TX, malonoben (1254)+TX, mazidox (1255)+TX, mecarbam (502)+TX, mecarphon (1258)+TX, menazon (1260)+TX, mephosfolan (1261)+TX, mercurous chloride (513)+TX, mesulfenfos (1263)+TX, metaflumizone (CCN)+TX, metam (519)+TX, metam-potassium (alternative name) (519)+TX, metam-sodium (519)+TX, methacrifos (1266)+TX, methamidophos (527)+TX, methanesulfonyl fluoride (IUPAC/Chemical Abstracts name) (1268)+TX, methidathion (529)+TX, methiocarb (530)+TX, methocrotophos (1273)+TX, methomyl (531)+TX, methoprene (532)+TX, methoquin-butyl (1276)+TX, methothrin (alternative name) (533)+TX, methoxychlor (534)+TX, methoxyfenozide (535)+TX, methyl bromide (537)+TX, methyl isothiocyanate (543)+TX, methylchloroform (alternative name) [CCN]+TX, methylene chloride [CCN]+TX, metofluthrin [CCN]+TX, metolcarb (550)+TX, metoxadiazone (1288)+TX, mevinphos (556)+TX, mexacarbate (1290)+TX, milbemectin (557)+TX, milbemycin oxime (alternative name) [CCN]+TX, mipafox (1293)+TX, mirex (1294)+TX, monocrotophos (561)+TX, morphothion (1300)+TX, moxidectin (alternative name) [CCN]+TX, naftalofos (alternative name) [CCN]+TX, naled (567)+TX, naphthalene (IUPAC/Chemical Abstracts name) (1303)+TX, NC-170 (development code) (1306)+TX, NC-184 (compound code)+TX, nicotine (578)+TX, nicotine sulfate (578)+TX, nifluridide (1309)+TX, nitenpyram (579)+TX, nithiazine (1311)+TX, nitrilacarb (1313)+TX, nitrilacarb 1:1 zinc chloride complex (1313)+TX, NNI-0101 (compound code)+TX, NNI-0250 (compound code)+TX, nornicotine (traditional name) (1319)+TX, novaluron (585)+TX, noviflumuron (586)+TX, O-5-dichloro-4-iodophenyl O-ethyl ethylphosphonothioate (IUPAC name) (1057)+TX, O,O-diethyl O-4-methyl-2-oxo-2H-chromen-7-yl phosphorothioate (IUPAC name) (1074)+TX, O,O-diethyl 0-6-methyl-2-propylpyrimidin-4-yl phosphorothioate (IUPAC name) (1075)+TX, O,O,O′,O′-tetrapropyl dithiopyrophosphate (IUPAC name) (1424)+TX, oleic acid (IUPAC name) (593)+TX, omethoate (594)+TX, oxamyl (602)+TX, oxydemeton-methyl (609)+TX, oxydeprofos (1324)+TX, oxydisulfoton (1325)+TX, pp′-DDT (219)+TX, para-dichlorobenzene [CCN]+TX, parathion (615)+TX, parathion-methyl (616)+TX, penfluron (alternative name) [CCN]+TX, pentachlorophenol (623)+TX, pentachlorophenyl laurate (IUPAC name) (623)+TX, permethrin (626)+TX, petroleum oils (alternative name) (628)+TX, PH 60-38 (development code) (1328)+TX, phenkapton (1330)+TX, phenothrin (630)+TX, phenthoate (631)+TX, phorate (636)+TX, phosalone (637)+TX, phosfolan (1338)+TX, phosmet (638)+TX, phosnichlor (1339)+TX, phosphamidon (639)+TX, phosphine (IUPAC name) (640)+TX, phoxim (642)+TX, phoxim-methyl (1340)+TX, pirimetaphos (1344)+TX, pirimicarb (651)+TX, pirimiphos-ethyl (1345)+TX, pirimiphos-methyl (652)+TX, polychlorodicyclopentadiene isomers (IUPAC name) (1346)+TX, polychloroterpenes (traditional name) (1347)+TX, potassium arsenite [CCN]+TX, potassium thiocyanate [CCN]+TX, prallethrin (655)+TX, precocene I (alternative name) [CCN]+TX, precocene II (alternative name) [CCN]+TX, precocene III (alternative name) [CCN]+TX, primidophos (1349)+TX, profenofos (662)+TX, profluthrin [CCN]+TX, promacyl (1354)+TX, promecarb (1355)+TX, propaphos (1356)+TX, propetamphos (673)+TX, propoxur (678)+TX, prothidathion (1360)+TX, prothiofos (686)+TX, prothoate (1362)+TX, protrifenbute [CCN]+TX, pymetrozine (688)+TX, pyraclofos (689)+TX, pyrazophos (693)+TX, pyresmethrin (1367)+TX, pyrethrin I (696)+TX, pyrethrin II (696)+TX, pyrethrins (696)+TX, pyridaben (699)+TX, pyridalyl (700)+TX, pyridaphenthion (701)+TX, pyrimidifen (706)+TX, pyrimitate (1370)+TX, pyriproxyfen (708)+TX, quassia (alternative name) [CCN]+TX, quinalphos (711)+TX, quinalphos-methyl (1376)+TX, quinothion (1380)+TX, quintiofos (1381)+TX, R-1492 (development code) (1382)+TX, rafoxanide (alternative name) [CCN]+TX, resmethrin (719)+TX, rotenone (722)+TX, RU 15525 (development code) (723)+TX, RU 25475 (development code) (1386)+TX, ryania (alternative name) (1387)+TX, ryanodine (traditional name) (1387)+TX, sabadilla (alternative name) (725)+TX, schradan (1389)+TX, sebufos (alternative name)+TX, selamectin (alternative name) [CCN]+TX, SI-0009 (compound code)+TX, SI-0205 (compound code)+TX, SI-0404 (compound code)+TX, SI-0405 (compound code)+TX, silafluofen (728)+TX, SN 72129 (development code) (1397)+TX, sodium arsenite [CCN]+TX, sodium cyanide (444)+TX, sodium fluoride (IUPAC/Chemical Abstracts name) (1399)+TX, sodium hexafluorosilicate (1400)+TX, sodium pentachlorophenoxide (623)+TX, sodium selenate (IUPAC name) (1401)+TX, sodium thiocyanate [CCN]+TX, sophamide (1402)+TX, spinosad (737)+TX, spiromesifen (739)+TX, spirotetrmat (CCN)+TX, sulcofuron (746)+TX, sulcofuron-sodium (746)+TX, sulfluramid (750)+TX, sulfotep (753)+TX, sulfuryl fluoride (756)+TX, sulprofos (1408)+TX, tar oils (alternative name) (758)+TX, tau-fluvalinate (398)+TX, tazimcarb (1412)+TX, TDE (1414)+TX, tebufenozide (762)+TX, tebufenpyrad (763)+TX, tebupirimfos (764)+TX, teflubenzuron (768)+TX, tefluthrin (769)+TX, temephos (770)+TX, TEPP (1417)+TX, terallethrin (1418)+TX, terbam (alternative name)+TX, terbufos (773)+TX, tetrachloroethane [CCN]+TX, tetrachlorvinphos (777)+TX, tetramethrin (787)+TX, theta-cypermethrin (204)+TX, thiacloprid (791)+TX, thiafenox (alternative name)+TX, thiamethoxam (792)+TX, thicrofos (1428)+TX, thiocarboxime (1431)+TX, thiocyclam (798)+TX, thiocyclam hydrogen oxalate (798)+TX, thiodicarb (799)+TX, thiofanox (800)+TX, thiometon (801)+TX, thionazin (1434)+TX, thiosultap (803)+TX, thiosultap-sodium (803)+TX, thuringiensin (alternative name) [CCN]+TX, tolfenpyrad (809)+TX, tralomethrin (812)+TX, transfluthrin (813)+TX, transpermethrin (1440)+TX, triamiphos (1441)+TX, triazamate (818)+TX, triazophos (820)+TX, triazuron (alternative name)+TX, trichlorfon (824)+TX, trichlormetaphos-3 (alternative name) [CCN]+TX, trichloronat (1452)+TX, trifenofos (1455)+TX, triflumuron (835)+TX, trimethacarb (840)+TX, triprene (1459)+TX, vamidothion (847)+TX, vaniliprole [CCN]+TX, veratridine (alternative name) (725)+TX, veratrine (alternative name) (725)+TX, XMC (853)+TX, xylylcarb (854)+TX, YI-5302 (compound code)+TX, zeta-cypermethrin (205)+TX, zetamethrin (alternative name)+TX, zinc phosphide (640)+TX, zolaprofos (1469) and ZXI 8901 (development code) (858)+TX, cyantraniliprole [736994-63-19+TX, chlorantraniliprole [500008-45-7]+TX, cyenopyrafen [560121-52-0]+TX, cyflumetofen [400882-07-7]+TX, pyrifluquinazon [337458-27-2]+TX, spinetoram [187166-40-1+187166-15-0]+TX, spirotetramat [203313-25-1]+TX, sulfoxaflor [946578-00-3]+TX, flufiprole [704886-18-0]+TX, meperfluthrin [915288-13-0]+TX, tetramethylfluthrin [84937-88-2]+TX, triflumezopyrim (disclosed in WO 2012/092115)+TX, 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

[0684] 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,

[0685] 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, a nitrification inhibitor selected from the group of substances consisting of potassium ethylxanthate [CCN] and nitrapyrin (580)+TX,

[0686] 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,

[0687] 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,

[0688] 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,

[0689] 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,

[0690] a virucide selected from the group of substances consisting of imanin (alternative name) [CCN] and ribavirin (alternative name) [CCN]+TX,

[0691] a wound protectant selected from the group of substances consisting of mercuric oxide (512)+TX, octhilinone (590) and thiophanate-methyl (802)+TX,

[0692] and biologically active compounds selected from the group consisting of azaconazole (60207-31-0]+TX, bitertanol [70585-36-3]+TX, bromuconazole [116255-48-2]+TX, cyproconazole [94361-06-5]+TX, difenoconazole [119446-68-3]+TX, diniconazole [83657-24-3]+TX, epoxiconazole [106325-08-0]+TX, fenbuconazole [114369-43-6]+TX, fluquinconazole [136426-54-5]+TX, flusilazole [85509-19-9]+TX, flutriafol [76674-21-0]+TX, hexaconazole [79983-71-4]+TX, imazalil [35554-44-0]+TX, imibenconazole [86598-92-7]+TX, ipconazole [125225-28-7]+TX, metconazole [125116-23-6]+TX, myclobutanil [88671-89-0]+TX, pefurazoate [101903-30-4]+TX, penconazole [66246-88-6]+TX, prothioconazole [178928-70-6]+TX, pyrifenox [88283-41-4]+TX, prochloraz [67747-09-5]+TX, propiconazole [60207-90-1]+TX, simeconazole [149508-90-7]+TX, tebucon-azole [107534-96-3]+TX, tetraconazole [112281-77-3]+TX, triadimefon [43121-43-3]+TX, triadimenol [55219-65-3]+TX, triflumizole [99387-89-0]+TX, triticonazole [131983-72-7]+TX, ancymidol [12771-68-5]+TX, fenarimol [60168-88-9]+TX, nuarimol [63284-71-9]+TX, bupirimate [41483-43-6]+TX, dimethirimol [5221-53-4]+TX, ethirimol [23947-60-6]+TX, dodemorph [1593-77-7]+TX, fenpropidine [67306-00-7]+TX, fenpropimorph [67564-91-4]+TX, spiroxamine [118134-30-8]+TX, tridemorph [81412-43-3]+TX, cyprodinil [121552-61-2]+TX, mepanipyrim [110235-47-7]+TX, pyrimethanil [53112-28-0]+TX, fenpiclonil [74738-17-3]+TX, fludioxonil [131341-86-1]+TX, benalaxyl [71626-11-4]+TX, furalaxyl [57646-30-7]+TX, metalaxyl [57837-19-1]+TX, R-metalaxyl [70630-17-0]+TX, ofurace [58810-48-3]+TX, oxadixyl [77732-09-3]+TX, benomyl [17804-35-2]+TX, carbendazim [10605-21-7]+TX, debacarb [62732-91-6]+TX, fuberidazole [3878-19-1]+TX, thiabendazole [148-79-8]+TX, chlozolinate [84332-86-5]+TX, dichlozoline [24201-58-9]+TX, iprodione [36734-19-7]+TX, myclozoline [54864-61-8]+TX, procymidone [32809-16-8]+TX, vinclozoline [50471-44-8]+TX, boscalid [188425-85-6]+TX, carboxin [5234-68-4]+TX, fenfuram [24691-80-3]+TX, flutolanil [66332-96-5]+TX, mepronil [55814-41-0]+TX, oxycarboxin [5259-88-1]+TX, penthiopyrad [183675-82-3]+TX, thifluzamide [130000-40-7]+TX, guazatine [108173-90-6]+TX, dodine [2439-10-3] [112-65-2] (free base)+TX, iminoctadine [13516-27-3]+TX, azoxystrobin [131860-33-8]+TX, dimoxystrobin [149961-52-4]+TX, enestroburin {Proc. BCPC, Int. Congr., Glasgow, 2003, 1, 93}+TX, fluoxastrobin [361377-29-9]+TX, kresoxim-methyl [143390-89-0]+TX, metominostrobin [133408-50-1]+TX, trifloxystrobin [141517-21-7]+TX, orysastrobin [248593-16-0]+TX, picoxystrobin [117428-22-5]+TX, pyraclostrobin [175013-18-0]+TX, ferbam [14484-64-1]+TX, mancozeb [8018-01-7]+TX, maneb [12427-38-2]+TX, metiram [9006-42-2]+TX, propineb [12071-83-9]+TX, thiram [137-26-8]+TX, zineb [12122-67-7]+TX, ziram [137-30-4]+TX, captafol [2425-06-1]+TX, captan [133-06-2]+TX, dichlofluanid [1085-98-9]+TX, fluoroimide [41205-21-4]+TX, folpet [133-07-3]+TX, tolylfluanid [731-27-1]+TX, bordeaux mixture [8011-63-0]+TX, copperhydroxid [20427-59-2]+TX, copperoxychlorid [1332-40-7]+TX, coppersulfat [7758-98-7]+TX, copperoxid [1317-39-1]+TX, mancopper [53988-93-5]+TX, oxine-copper [10380-28-6]+TX, dinocap [131-72-6]+TX, nitrothal-isopropyl [10552-74-6]+TX, edifenphos [17109-49-8]+TX, iprobenphos [26087-47-8]+TX, isoprothiolane [50512-35-1]+TX, phosdiphen [36519-00-3]+TX, pyrazophos [13457-18-6]+TX, tolclofos-methyl [57018-04-9]+TX, acibenzolar-S-methyl [135158-54-2]+TX, anilazine [101-05-3]+TX, benthiavalicarb [413615-35-7]+TX, blasticidin-S [2079-00-7]+TX, chinomethionat [2439-01-2]+TX, chloroneb [2675-77-6]+TX, chlorothalonil [1897-45-6]+TX, cyflufenamid [180409-60-3]+TX, cymoxanil [57966-95-7]+TX, dichlone [117-80-6]+TX, diclocymet [139920-32-4]+TX, diclomezine [62865-36-5]+TX, dicloran [99-30-9]+TX, diethofencarb [87130-20-9]+TX, dimetho-morph [110488-70-5]+TX, SYP-L190 (Flumorph) [211867-47-9]+TX, dithianon [3347-22-6]+TX, ethaboxam [162650-77-3]+TX, etridiazole [2593-15-9]+TX, famoxadone [131807-57-3]+TX, fenamidone [161326-34-7]+TX, fenoxanil [115852-48-7]+TX, fentin [668-34-8]+TX, ferimzone [89269-64-7]+TX, fluazinam [79622-59-6]+TX, fluopicolide [239110-15-7]+TX, flusulfamide [106917-52-6]+TX, fenhexamid [126833-17-8]+TX, fosetyl-aluminium [39148-24-8]+TX, hymexazol [10004-44-1]+TX, iprovalicarb [140923-17-7]+TX, IKF-916 (Cyazofamid) [120116-88-3]+TX, kasugamycin [6980-18-3]+TX, methasulfocarb [66952-49-6]+TX, metrafenone [220899-03-6]+TX, pencycuron [66063-05-6]+TX, phthalide [27355-22-2]+TX, polyoxins [11113-80-7]+TX, probenazole [27605-76-1]+TX, propamocarb [25606-41-1]+TX, proquinazid [189278-12-4]+TX, pyroquilon [57369-32-1]+TX, quinoxyfen [124495-18-7]+TX, quintozene [82-68-8]+TX, sulfur [7704-34-9]+TX, tiadinil [223580-51-6]+TX, triazoxide [72459-58-6]+TX, tricyclazole [41814-78-2]+TX, triforine [26644-46-2]+TX, validamycin [37248-47-8]+TX, zoxamide (RH7281) [156052-68-5]+TX, mandipropamid [374726-62-2]+TX, isopyrazam [881685-58-1]+TX, sedaxane [874967-67-6]+TX, 3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid (9-dichloromethylene-1,2,3,4-tetrahydro-1,4-methano-naphthalen-5-yl)-amide (disclosed in WO 2007/048556)+TX, 3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid (3′,4′,5′-trifluoro-biphenyl-2-yl)-amide (disclosed in WO 2006/087343)+TX, [(3S,4R,4aR,6S,6aS,12R,12aS,12bS)-3-[(cyclopropylcarbonyl)oxy]-1,3,4,4a,5,6,6a,12,12a,12b-decahydro-6,12-dihydroxy-4,6a,12b-trimethyl-11-oxo-9-(3-pyridinyl)-2H,11Hnaphtho[2,1-b]pyrano[3,4-e]pyran-4-yl]methyl-cyclopropanecarboxylate [915972-17-7]+TX and 1,3,5-trimethyl-N-(2-methyl-1-oxopropyl)-N-[3-(2-methylpropyl)-4-[2,2,2-trifluoro-1-methoxy-1-(trifluoromethyl)ethyl]phenyl]-1H-pyrazole-4-carboxamide [926914-55-8]+TX; 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; 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; rescalure [64309-03-1]+TX; aminopyrifen [1531626-08-0]+TX; tyclopyrazoflor [1477919-27-9]+TX; and spiropidion [1229023-00-0]+TX; and microbials including: Acinetobacter Iwoffii+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 (AQ10®)+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 CrylAb+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 C.sub.9-1®)+TX, Pantoea spp.+TX, Pasteuria spp. (Econem®)+TX, Pasteuria nishizawae+TX, Penicillium aurantiogriseum+TX, Penicillium bil/ai (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 HCO+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

[0693] 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

[0694] 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 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 citricola+TX, Ageniaspis fuscicollis+TX, Amblyseius andersoni (Anderline®+TX, Andersoni-System®)+TX, Amblyseius californicus (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 californicus+TX, Eretmocerus eremicus (Ercal®+TX, Eretline E®)+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 californicus+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

[0695] other biologicals including: abscisic acid+TX, bioSea®+TX, Chondrostereum purpureum (Chontrol Paste®)+TX, Colletotrichum gloeosporioides (Collego®)+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 (Sil-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;

[0696] 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, flufenpyrrolidone+TX, inpyrfluxam+TX or indiflumetpyr+TX, isoflucypram+TX, isocycloseram+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, cyetpyrafen+TX, etpyrafen+TX or, 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, dimesulfazet+TX, cyclobutrifluram+TX, flubeneteram+TX, flupentiofenox+TX and Flupyradifurone+TX.

[0697] The references in brackets behind the active ingredients, e.g. [3878-19-1] refer to the Chemical Abstracts Registry number. The above described mixing partners are known. Where the active ingredients are included in “The Pesticide Manual” [The Pesticide Manual—A World Compendium; Thirteenth Edition; Editor: C. D. S. TomLin; The British Crop Protection Council], they are described therein under the entry number given in round brackets hereinabove for the particular compound; for example, the compound “abamectin” is described under entry number (1). Where “[CCN]” is added hereinabove to the particular compound, the compound in question is included in the “Compendium of Pesticide Common Names”, which is accessible on the internet [A. Wood; Compendium of Pesticide Common Names, Copyright © 1995-2004]; for example, the compound “acetoprole” is described under the internet address http://www.alanwood.net/pesticides/acetoprole.html.

[0698] 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 “develoment 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.

[0699] The active ingredient mixture of the compounds of formula I selected from Tables A-1 to A-81 and Tables B-1 to B-54 and Table P with active ingredients described above comprises a compound selected from Tables A-1 to A-81 and Tables B-1 to B-54 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.

[0700] 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.

[0701] The mixtures comprising a compound of formula I selected from Tables A-1 to A-81 and Tables B-1 to B-54 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-81 and Tables B-1 to B-54 Table P and the active ingredients as described above is not essential for working the present invention.

[0702] 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.

[0703] 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.

[0704] The application methods for the compositions, that is the methods of controlling pests of the abovementioned type, such as spraying, atomizing, dusting, brushing on, dressing, scattering or pouring—which are to be selected to suit the intended aims of the prevailing circumstances—and the use of the compositions for controlling pests of the abovementioned type are other subjects of the invention. Typical rates of concentration are between 0.1 and 1000 ppm, preferably between 0.1 and 500 ppm, of active ingredient. The rate of application per hectare is generally 1 to 2000 g of active ingredient per hectare, in particular 10 to 1000 g/ha, preferably 10 to 600 g/ha.

[0705] 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.

[0706] 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.

[0707] 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.

[0708] 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).

[0709] 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

[0710] 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: Activity Against Bemisia tabaci (Cotton White Fly)

[0711] 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: P1, P2, P9, P11, P13, P14 and P16.

Example B2: Activity Against Diabrotica Balteata (Corn Root Worm)

[0712] 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.

[0713] 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:

[0714] P1, P2, P5, P9, P11, P13, P14, P16, P18 and P20.

Example B3: Activity Against Euschistus heros (Neotropical Brown Stink Bug)

[0715] 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.

[0716] 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:

[0717] P1, P2, P5, P11, P13, P14, P15, P16, P18 and P20.

Example B4: Activity Against Plutella xylostella (Diamond Back Moth)

[0718] 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.

[0719] 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:

[0720] P1, P2, P5, P9, P11, P13, P14, P16, P18 and P20.

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

[0721] 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.

[0722] The following compounds resulted in at least 80% mortality at an application rate of 200 ppm:

[0723] P1, P2, P5, P9, P11, P14, P15, P16, P18 and P20.

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

[0724] 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.

[0725] The following compounds resulted in at least 80% mortality at a test rate of 24 ppm:

[0726] P1, P2, P5, P9, P11, P13, P14, P15, P16, P18 and P20.

Example B7: Activity Against Spodoptera littoralis (Egyptian Cotton Leaf Worm)

[0727] 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.

[0728] The following compounds resulted in at least 80% control at an application rate of 200 ppm:

[0729] P2, P11, P13, P14, P16, P18 and P20.