WO2018041729A2

WO2018041729A2 - Pesticidally active heterocyclic derivatives with sulphur containing substituents

Info

Publication number: WO2018041729A2
Application number: PCT/EP2017/071400
Authority: WO
Inventors: Pierre Joseph Marcel Jung; Michel Muehlebach; Andrew Edmunds; Peter Renold; Anke Buchholz
Original assignee: Syngenta Participations Ag
Priority date: 2016-09-01
Filing date: 2017-08-25
Publication date: 2018-03-08
Also published as: WO2018041729A3

Abstract

Compounds of formula I, wherein the substituents are as defined in claim 1, and the agrochemically acceptable salts, stereoismers, enantiomers, tautomers and N-oxides of those compounds, can be used as insecticides and can be prepared in a manner known per se.

Description

Pesticidally active heterocyclic derivatives with sulphur containing substituents

The present invention relates to pesticidally active, in particular insecticidally active heterocyclic derivatives containing sulphur substituents, to processes for their preparation, to compositions comprising those compounds, and to their use for controlling animal pests, including arthropods and in particular insects or representatives of the order Acarina.

Heterocyclic compounds with pesticidal action are known and described, for example, in

WO 2010/125985, WO 2013/018928 and WO2016/024587. There have now been found novel pesticidally active heterocyclic imidazole and triazole derivatives with sulphur containing phenyl and pyridyl substituents.

The present invention accordingly relates to compounds of formula I,

wherein

Gi is nitrogen or CF¾;

G2 is a five- to six-membered, aromatic, partially saturated or fully saturated ring system linked via a nitrogen atom to the imidazole or triazole ring which contains the group Gi, said ring system can be mono- or polysubstituted by substituents selected from the group consisting of halogen, cyano, Ci-C4alkyl, Ci-C4haloalkyl, Ci-C4haloalkoxy, Ci-C4alkoxy, Ci-C4alkylsulfanyl, Ci-C4alkylsulfinyl, Ci-C4alkylsulfonyl, -C(0)Ci-C4alkyl, Ci-C4haloalkylsulfanyl, Ci-C4haloalkylsulfinyl,

Ci-C4haloalkylsulfonyl and -C(0)Ci-C4haloalkyl; and said ring system contains 1 , 2 or 3 heteroatoms selected from the group consisting of nitrogen, oxygen and sulfur, where said ring system may not contain more than one oxygen atom and not more than one sulfur atom; or

G2 is a five-membered, aromatic, partially saturated or fully saturated ring system linked via a carbon atom to the imidazole or triazole ring which contains the group Gi , said ring system can be mono- or polysubstituted by substituents selected from the group consisting of halogen, cyano, Ci-C4alkyl,

Ci-C4haloalkyl, Ci-C4haloalkoxy, Ci-C4alkoxy, Ci-C4alkylsulfanyl, Ci-C4alkylsulfinyl, Ci-C4alkylsulfonyl, -C(0)Ci-C4alkyl, Ci-C4haloalkylsulfanyl, Ci-C4haloalkylsulfinyl, Ci-C4haloalkylsulfonyl and

-C(0)Ci-C4haloalkyl; and said ring system can contain 1 , 2 or 3 heteroatoms selected from the group consisting of nitrogen, oxygen and sulfur, where said ring system may not contain more than one oxygen atom and not more than one sulfur atom; or G2 is a six-membered, partially saturated or fully saturated ring system linked via a carbon atom to the imidazole or triazole ring which contains the group Gi, said ring system can be mono- or

polysubstituted by substituents selected from the group consisting of halogen, cyano, Ci-C4alkyl, Ci-C4haloalkyl, Ci-C4haloalkoxy, Ci-C4alkoxy, Ci-C4alkylsulfanyl, Ci-C4alkylsulfinyl, Ci-C4alkylsulfonyl, -C(0)Ci-C4alkyl, Ci-C4haloalkylsulfanyl, Ci-C4haloalkylsulfinyl, Ci-C4haloalkylsulfonyl and

-C(0)Ci-C4haloalkyl; and said ring system can contain 1, 2 or 3 heteroatoms selected from the group consisting of nitrogen, oxygen and sulfur, where said ring system may not contain more than one oxygen atom and not more than one sulfur atom;

Re is hydrogen, Ci-C4alkyl or Ci-C4haloalkyl;

R9 is hydrogen, Ci-C4alkyl, Ci-C4haloalkyl, cyano or halogen;

R7 is a radical selected from the group consisting of formula Qi and Q2

Qi Q2

wherein the arrow denotes the point of attachment to the imidazole or triazole ring;

and wherein A represents CH or N;

Q is hydrogen, halogen, Ci-C6haloalkoxy or Ci-C6haloalkyl; or

Q is phenyl which can be mono- or polysubstituted by substituents selected from the group consisting of halogen, cyano, Ci-C4alkyl, Ci-C4haloalkyl, Ci-C4haloalkoxy, Ci-C4alkoxy, Ci-C4haloalkylsulfanyl, Ci-C4haloalkylsulfinyl, Ci-C4haloalkylsulfonyl and -C(0)Ci-C4haloalkyl; or

Q is a five- to ten-membered monocyclic or fused bicyclic ring system linked via a carbon atom to the ring which contains the group A, said ring system can be aromatic, partially saturated or fully saturated and contains 1 to 4 hetero atoms selected from the group consisting of nitrogen, oxygen and sulfur, it not being possible for each ring system to contain more than 2 oxygen atoms and more than 2 sulfur atoms, said five- to ten-membered ring system can be mono- to polysubstituted by substituents independently selected from the group consisting of halogen, cyano, Ci-C4alkyl, Ci-C4haloalkyl, Ci- C4haloalkoxy, Ci-C4alkoxy, Ci-C4alkylsulfanyl, Ci-C4alkylsulfinyl, Ci-C4alkylsulfonyl, -C(0)Ci-C4alkyl, Ci-C4haloalkylsulfanyl, Ci-C4haloalkylsulfinyl, Ci-C4haloalkylsulfonyl and -C(0)Ci-C4haloalkyl; or Q is a five- to six-membered, aromatic, partially saturated or fully saturated ring system linked via a nitrogen atom to the ring which contains the group A, said ring system can be mono- or

polysubstituted by substituents selected from the group consisting of halogen, cyano, Ci-C4alkyl, Ci- C4haloalkyl, Ci-C4haloalkoxy, Ci-C4alkoxy, Ci-C4alkylsulfanyl, Ci-C4alkylsulfinyl, Ci-C4alkylsulfonyl, -C(0)Ci-C4alkyl, Ci-C4haloalkylsulfanyl, Ci-C4haloalkylsulfinyl, Ci-C4haloalkylsulfonyl and -C(0)Ci-C4haloalkyl; and said ring system contains 1 , 2 or 3 heteroatoms selected from the group consisting of nitrogen, oxygen and sulfur, where said ring system may not contain more than one oxygen atom and not more than one sulfur atom; or

Q is C3-C6cycloalkyl, or C3-C6cycloalkyl mono- or polysubstituted by substituents selected from the group consisting of halogen, cyano, Ci-C4alkyl, Ci-C4haloalkyl, C3-C6cycloalkyl and phenyl, wherein said phenyl can be mono- or polysubstituted by substituents selected from the group consisting of halogen, cyano, Ci-C4alkyl, Ci-C4haloalkyl, Ci-C4haloalkoxy, Ci-C4alkoxy, Ci-C4haloalkylsulfanyl, Ci- C4haloalkylsulfinyl, Ci-C4haloalkylsulfonyl and -C(0)Ci-C4haloalkyl; or

Q is C2-C6alkenyl, or C2-C6alkenyl mono- or polysubstituted by substituents selected from the group consisting of halogen, cyano, Ci-C4alkyl, Ci-C4haloalkyl, C3-C6cycloalkyl and phenyl, wherein said phenyl can be mono- or polysubstituted by substituents selected from the group consisting of halogen, cyano, Ci-C4alkyl, Ci-C4haloalkyl, Ci-C4haloalkoxy, Ci-C4alkoxy, Ci-C4haloalkylsulfanyl, Ci-C4halo- alkylsulfinyl, Ci-C4haloalkylsulfonyl and -C(0)Ci-C4haloalkyl; or

Q is C2-C6alkynyl, or C2-C6alkynyl mono- or polysubstituted by substituents selected from the group consisting of halogen, cyano, Ci-C4alkyl, Ci-C4haloalkyl, C3-C6cycloalkyl, tri(Ci-C4alkyl)silyl and phenyl, wherein said phenyl can be mono- or polysubstituted by substituents selected from the group consisting of halogen, cyano, Ci-C4alkyl, Ci-C4haloalkyl, Ci-C4haloalkoxy, Ci-C4alkoxy, Ci-C4halo- alkylsulfanyl, Ci-C4haloalkylsulfinyl, Ci-C4haloalkylsulfonyl and -C(0)Ci-C4haloalkyl; or

Q is Ci-C6haloalkylsulfanyl, Ci-C6haloalkylsulfinyl, Ci-C6haloalkylsulfonyl, -C(0)Ci-C4haloalkyl, Ci-C6alkylsulfanyl, Ci -Ceal ky Is u If i ny I , or Ci-C6alkylsulfonyl;

X is S, SO or S0₂; and

Ri is Ci-C4alkyl, Ci-C4haloalkyl, C3-C6cycloalkyl, C3-C6cycloalkyl-Ci-C4alkyl; or

Ri is C3-C6cycloalkyl mono - or polysubstituted by substituents selected from the group consisting of halogen, cyano and Ci-C4alkyl; or

Ri is C3-C6cycloalkyl-Ci-C4alkyl mono- or polysubstituted by substituents selected from the group consisting of halogen, cyano and Ci-C4alkyl; or

Ri is C2-C6alkenyl, C2-C6haloalkenyl or C2-C6alkynyl; and

with the proviso that when Gi is CR9, then the ring system G2 is not aromatic;

and agrochemically acceptable salts, stereoismers, enantiomers, tautomers and N-oxides of the compounds of formula I .

Compounds of formula I which have at least one basic centre can form, for example, acid addition salts, for example with strong inorganic acids such as mineral acids, for example perchloric acid, sulfuric acid, nitric acid, nitrose acid, a phosphorus acid or a hydrohalic acid, with strong organic carboxylic acids, such as Ci-C4alkanecarboxylic acids which are unsubstituted or substituted, for example by halogen, for example acetic acid, such as saturated or unsaturated dicarboxylic acids, for example oxalic acid , malonic acid, succinic acid, maleic acid, fumaric acid or phthalic acid, such as hydroxycarboxylic acids, for example ascorbic acid, lactic acid , malic acid, tartaric acid or citric acid, or such as benzoic acid, or with organic sulfonic acids, such as Ci-C4alkane- or arylsulfonic acids which are unsubstituted or substituted, for example by halogen, for example methane- or p-toluenesulfonic acid. Compounds of formula I which have at least one acidic group can form, for example, salts with bases, for example mineral salts such as alkali metal or alkaline earth metal salts, for example sodium, potassium or magnesium salts, or salts with ammonia or an organic amine, such as morpholine, piperidine, pyrrolidine, a mono-, di- or tri-lower-alkylamine, for example ethyl-, diethyl-, triethyl- or dimethylpropylamine, or a mono-, di- or trihydroxy-lower-alkylamine, for example mono-, di- or triethanolamine.

The alkyl groups occurring in the definitions of the substituents can be straight-chain or branched and are, for example, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, iso-butyl, tert-butyl, pentyl, hexyl, nonyl, decyl and their branched isomers. Alkylsulfanyl, alkylsulfinyl, alkylsulfonyl, alkoxy, alkenyl and alkynyl radicals are derived from the alkyl radicals mentioned. The alkenyl and alkynyl groups can be mono- or polyunsaturated.

Halogen is generally fluorine, chlorine, bromine or iodine. This also applies, correspondingly, to halogen in combination with other meanings, such as haloalkyl or halophenyl.

HaloalkyI groups preferably have a chain length of from 1 to 6 carbon atoms. Haloalkyl is, for example, fluoromethyl, difluoromethyl, trifluoromethyl, chloromethyl, dichloromethyl, trichloromethyl, 2,2,2- trifluoroethyl, 2-fluoroethyl, 2-chloroethyl, pentafluoroethyl, 1 ,1-difluoro-2,2,2-trichloroethyl, 2,2,3,3- tetrafluoroethyl and 2,2,2-trichloroethyl; preferably trichloromethyl, difluorochloromethyl,

difluoromethyl, trifluoromethyl and dichlorofluoromethyl.

Alkoxy groups preferably have a preferred chain length of from 1 to 6 carbon atoms. Alkoxy is, for example, methoxy, ethoxy, propoxy, i-propoxy, n-butoxy, isobutoxy, sec-butoxy and tert-butoxy and also the isomeric pentyloxy and hexyloxy radicals; preferably methoxy and ethoxy.

Alkoxyalkyl groups preferably have a chain length of 1 to 6 carbon atoms.

Alkoxyalkyl is, for example, methoxymethyl, methoxyethyl, ethoxymethyl, ethoxyethyl, n- propoxymethyl, n-propoxyethyl, isopropoxymethyl or isopropoxyethyl.

Alkylsulfanyl is for example methylsulfanyl, ethylsulfanyl, propylsulfanyl, isopropylsulfanyl,

butylsulfanyl, pentylsulfanyl, and hexylsulfanyl.

Alkylsulfinyl is for example methylsulfinyl, ethylsulfinyl, propylsulfinyl, isopropylsulfinyl, a butylsulfinyl, pentylsulfinyl, and hexylsulfinyl.

Alkylsulfonyl is for example methylsulfonyl, ethylsulfonyl, propylsulfonyl, isopropylsulfonyl,

butylsulfonyl, pentylsulfonyl, and hexylsulfonyl. The cycloalkyl groups preferably have from 3 to 6 ring carbon atoms, for example cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl.

Haloalkoxy groups preferably have a chain length of from 1 to 4 carbon atoms. Haloalkoxy is, for example, difluoromethoxy, trifluoromethoxy or 2,2,2-trifluoroethoxy. Haloalkylsulfanyl groups preferably have a chain length of from 1 to 4 carbon atoms. Haloalkylsulfanyl is, for example, difluoromethylsulfanyl, trifluoromethylsulfanyl or 2,2,2-trifluoroethylsulfanyl. Similar considerations apply to the radicals Ci-C4haloalkylsulfinyl and Ci-C4haloalkylsulfonyl, which may be, for example, trifluoromethylsulfinyl, , trifluoromethylsulfonyl or 2,2,2-trifluoroethylsulfonyl.

In the context of this invention, examples of Q being a five- to six-membered, aromatic, partially saturated or fully saturated ring system that are linked via a nitrogen atom to the ring which contains the group A, are selected from pyrazole, pyrazoline, pyrazolidine, pyrrole, pyrroline, pyrrolidine, pyrrol id ine-2-one, piperidine, piperazine, morpholine, imidazole, imidazoline, imidazolidine, triazole and pyridine-2-one.

In the context of this invention "mono- to polysubstituted" in the definition of the substituents, means typically, depending on the chemical structure of the substituents, monosubstituted to seven-times substituted, preferably monosubstituted to five-times substituted, more preferably mono-, double- or triple-substituted.

Free radicals represents methyl groups.

The compounds of formula I according to the invention also include hydrates which may be formed during the salt formation.

According to the present invention, Q as a five- to ten-membered monocyclic or fused bicyclic ring system that is linked via a carbon atom to the ring which contains the group A, said ring system can be aromatic, partially saturated or fully saturated and contains 1 to 4 hetero atoms selected from the group consisting of nitrogen, oxygen and sulfur, it not being possible for each ring system to contain more than 2 oxygen atoms and more than 2 sulfur atoms,

or Q as a three- to ten-membered, monocyclic or fused bicyclic ring system which may be aromatic, partially saturated or fully saturated,

is, depending of the number of ring members, preferably selected from the group consisting of the following heterocyclic groups:

pyrrolyl; pyrazolyl; isoxazolyl; furanyl; thienyl; imidazolyl; oxazolyl; thiazolyl; isothiazolyl; triazolyl; oxadiazolyl; thiadiazolyl; tetrazolyl; furyl; pyridyl; pyrimidyl; pyrazinyl; pyridazinyl; triazinyl, pyranyl; quinazolinyl; isoquinolinyl; indolizinyl; isobenzofuranylnaphthyridinyl; quinoxalinyl; cinnolinyl;

phthalazinyl; benzothiazolyl; benzoxazolyl; benzotriazolyl; indazolyl; indolyl; (1 H-pyrrol-1-yl)-; (1 H- pyrrol-2-yl)-; (1 H-pyrrol-3-yl)-; (1 H-pyrazol-1-yl)-; (1 H-pyrazol-3-yl)-; (3H-pyrazol-3-yl)-; (1 H-pyrazol-4- yl)-; (3-isoxazolyl)-; (5-isoxazolyl)-; (2-furanyl)-; (3-furanyl)-; (2-thienyl)-; (3-thienyl)-; (1 H-imidazol-2-yl)- ; (1 H- imidazol-4-yl)-; (1 H-imidazol-5-yl)-; (2-oxazol-2-yl)-; (oxazol-4-yl)-; (oxazol-5-yl)-; (thiazol-2-yl)-; (thiazol-4-yl)-; (thiazol-5-yl)-; (isothiazol-3-yl)-; (isothiazol-5-yl)-; (1 H-1 ,2,3-triazol-1-yl)-; (I H-1 ,2,4- triazol-3-yl)-; (4H-1 ,2,4-triazol-4-yl)-; (1 H-1 ,2,4-triazol-1-yl)-; (1 ,2,3-oxadiazol-2-yl)-; (1 ,2,4-oxadiazol-3- yl)-; (1 ,2,4-oxadiazol-4-yl)-; (1 ,2,4-oxadiazol-5-yl)-; (1 ,2,3-thiadiazol-2-yl)-; (1 ,2,4-thiadiazol-3-yl)-; (1 ,2,4-thiadiazol-4-yl)-; (1 ,3,4-thiadiazol-5-yl)-; (1 H-tetrazol-1-yl)-; (1 H-tetrazol-5-yl)-; (2H-tetrazol-5-yl)- ; (2-pyridyl)-; (3-pyridyl)-; (4-pyridyl)-; (2-pyrimidinyl)-; (4-pyrimidinyl)-; (5-pyrimidinyl)-;(2-pyrazinyl)-; (3-pyridazinyl)-; (4-pyridazinyl)-; (1 ,3,5-triazin-2-yl)-; (1 ,2,4-triazin-5-yl)-; (1 ,2,4-triazin-6-yl)-; (1 ,2,4- triazin-3-yl)-;(furazan-3-yl)-; (2-quinolinyl)-; (3-quinolinyl)-; (4-quinolinyl)-; (5-quinolinyl)-; (6-quinolinyl)- ; (3-isoquinolnyl)-; (4-isoquinolnyl)-; (2-quinozolinyl)-; (2-quinoxalinyl)-; (5-quinoxalinyl)-; (pyrido[2,3- b]pyrazin-7-yl)-; (benzoxazol-5-yl)-; (benzothiazol-5-yl)-; (benzo[b]thien-2-yl)- and

(benzo[1 ,2,5]oxadiazol-5-yl)-; indolinyl and tetrahydroquinolynyl.

In preferred compounds of formula I, Q is selected from the group consisting of J-0 to J-48 (where the arrow represents the point of attachment of the group J to the ring which contains the group A):

J-0 J-1 J-2 J-3 J-4 J-5

J-6 J-7 J-8 J-10 J-11

J-12 J-13 J-14 J-15 J-16

J-17 J-18 J-19 J-20 J-21 J-22

J-23 J-24 J-25 J-26 J-27 J-28

J-29 J-30 J-31 J-32 J-33 J-34

wherein each group J-0 to J-48 is mono-, di- or trisubstituted with Rx, wherein

each Rx is, independently selected from the group consisting of hydrogen, halogen, cyano, Ci-C4alkyl, Ci-C4haloalkyl, Ci-C4haloalkoxy, Ci-C4alkoxy, Ci-C4alkylsulfanyl, Ci-C4alkylsulfinyl, Ci-C4alkylsulfonyl, -C(0)Ci-C₄alkyl, Ci-C₄haloalkylsulfanyl, Ci-C₄haloalkylsulfinyl, Ci-C₄haloalkylsulfonyl and -C(0)Ci- C4haloalkyl.

Also preferred are compounds of formula 1-1 wherein Q is selected from the group consisting of hydrogen, halogen, Ci-C6haloalkoxy, Ci-C6haloalkyl, Ci-C6haloalkylsulfanyl, Ci-C6haloalkylsulfinyl, Ci- Cehaloalkylsulfonyl or -C(0)Ci-C₄haloalkyl.

In the context of this invention, examples of G2 being a five- to six-membered, aromatic, partially saturated or fully saturated ring system linked via a nitrogen atom to the imidazole or triazole ring which contains the group Gi, are selected from pyrazole, pyrazoline, pyrazolidine, pyrrole, pyrroline, pyrrolidine, pyrrolidine-2-one, piperidine, piperazine, morpholine, imidazole, imidazoline,

imidazolidine, triazole and pyridine-2-one.

According to the present invention, G2 as a five-membered, aromatic, partially saturated or fully saturated ring system linked via a carbon atom to the imidazole or triazole ring which contains the group Gi, is preferably selected from the group consisting of the following heterocyclic groups:

pyrrolyl; furanyl; thiophenyl; oxazolyl; isoxazolyl; thiazolyl; isothiazolyl; imidazolyl; triazolyl; oxadiazolyl; thiadiazolyl; tetrazolyl and pyrazolyl.

According to the present invention, G2 as a six-membered, partially saturated or fully saturated ring system linked via a carbon atom to the imidazole or triazole ring which contains the group Gi, is preferably selected from the group consisting of the following heterocyclic groups:

piperidinyl, tetrahydropyridinyl, piperazinyl, tetrahydropyrazinyl, morpholinyl and pyridine-2-one.

In preferred compounds of formula I, G2 is selected from the group consisting of G-0 to G-37 (where the arrow represents the point of attachment of the group G to the imidazole or triazole ring which contains the group Gi):

G-5

G-11

G-17

-23

G-36 G-37 wherein each group G-0 to G-37 is mono-, di- or trisubstituted with Rx, wherein

each Rx is, independently selected the group consisting of hydrogen, halogen, cyano, Ci-C4alkyl, Ci

C4haloalkyl, Ci-C4haloalkoxy, Ci-C4alkoxy, Ci-C4alkylsulfanyl, Ci-C4alkylsulfinyl, Ci-C4alkylsulfonyl,

C(0)Ci-C₄alkyl, Ci-C₄haloalkylsulfanyl, Ci-C₄haloalkylsulfinyl, Ci-C₄haloalkylsulfonyl and -C(0)Ci-

C4haloalkyl.

A preferred group of compounds of formula I is represented by the compounds of formula 1-1

wherein A is as defined under formula I above; Qai and G2-1 are as defined by Q and G2 under formula I above; Xi is S, SO or SO2; R11 is methyl, ethyl, n-propyl, i-propyl or cyclopropylmethyl; Re is as defined above under formula I , preferably methyl; Gn is N or CR9 in which R9 is as defined above under formula I , preferably N or CH; and agrochemically acceptable salts, stereoismers, enantiomers, tautomers and N-oxides of those compounds.

Also preferred are compounds of formula 1-1 wherein G2-1 is selected from the group consisting of G-0 to G-37:

G-36 G-37

wherein each group G-0 to G-37 is mono-, di- or trisubstituted with Rx, wherein

More preferred are compounds of formula 1-1 wherein G2-1 is selected from the group consisting of

wherein each group G is mono-, di- or trisubstituted with Rx, wherein each Rx is, independently selected from the group consisting of hydrogen, Ci-C4alkyl and Ci-C4haloalkyl; preferably, each Rx is, independently selected from the group consisting of hydrogen, methyl and trifluoromethyl.

In an especially preferred group of compounds of formula 1-1 , G2-1 is selected from the group consisting of

G-₄a G-28a G-29a

wherein each Rx is, independently selected from the group consisting of hydrogen, Ci-C4alkyl and Ci- C4haloalkyl; preferably from hydrogen, methyl and trifluoromethyl.

In said especially preferred group of compounds of formula 1-1 , Re is preferably methyl and Gn is preferably N or CH. A further preferred embodiment of said especially preferred group of compounds of formula 1-1 comprises compounds wherein A is preferably N, Xi is preferably SO2 and Rn is preferably ethyl.

In compounds of formula 1-1 and all of the preferred embodiments of compounds of formula 1-1 mentioned above, Qai is preferably selected from the group consisting of hydrogen, halogen, Ci-C6haloalkoxy, Ci-C6haloalkyl, Ci-C6haloalkylsulfanyl, Ci-C6haloalkylsulfinyl, Ci-C6haloalkylsulfonyl, - -C4haloalkyl, and from the group consisting of J-0 to J-48:

J-0 J-1 J-2 J-3 J-4 J-5

J-6 J-7 J-8 J-9 J-10 J-11

J-12 J-13 J-14 J-15 J-16

J-17 J-18 J-20 J-21 J-22

J-23 J-24 J-25 J-26 J-27 J-28

J-29 J-30 J-31 J-32 J-33 J-34

wherein each group J-0 to J-48 is mono-, di- or trisubstituted with Rx, wherein

In compounds of formula 1-1 and all of the preferred embodiments of compounds of formula 1-1 mentioned above, Qai is even more preferably Ci-C6haloalkyl. Another preferred group of compounds of formula I is represented by the compounds of formula I-2

wherein A is as defined under formula I above; G2-2 is as defined by G2 under formula I above; X2 is S, SO or SO2; R12 is methyl, ethyl, n-propyl, i-propyl or cyclopropylmethyl; Re is as defined above under formula I, preferably methyl; G12 is N or CR9 in which R9 is as defined above under formula I, preferably N or CH;

and wherein Qa∑ is selected from the group consisting of hydrogen, halogen, Ci-C6haloalkoxy, Ci Cehaloalkyl, Ci-C6haloalkyl-sulfanyl, Ci-C6haloalkylsulfinyl, Ci-C6haloalkylsulfonyl, -C(0)Ci- C haloalkyl, and from the group consistin of J-0 to J-48:

J-0 J-1 J-2 J-3 J-4 J-5

J-6 J-8 J-10 J-1 1

J-12 J-13 J-14 J-15 J-16

J-23 J-24 J-25 J-26 J-27 J-28

J-29 J-30 J-31 J-32 j-33 J-34

wherein each group J-0 to J-48 is mono-, di- or trisubstituted with Rx, wherein each Rx is, independently selected from the group consisting of hydrogen, halogen, cyano, Ci-C4alkyl, Ci-C4haloalkyl, Ci-C4haloalkoxy, Ci-C4alkoxy, Ci-C4alkylsulfanyl, Ci-C4alkylsulfinyl, Ci-C4alkylsulfonyl, -C(0)Ci-C₄alkyl, Ci-C₄haloalkylsulfanyl, Ci-C₄haloalkylsulfinyl, Ci-C₄haloalkylsulfonyl and -C(0)Ci- C4haloalkyl;

and agrochemically acceptable salts, stereoismers, enantiomers, tautomers and N-oxides of those compounds.

More preferred are compounds of formula I-2 wherein Qa∑ is selected from Ci-C6haloalkyl.

Even more preferred compounds of formula I-2 are those, in which Qa∑ is trifluoromethyl.

In said especially preferred group of compounds of formula I-2, Re is preferably methyl and G12 is preferably N or CH. A further preferred embodiment of said especially preferred group of compounds of formula I-2 comprises compounds wherein A is preferably N, X2 is preferably SO2 and R12 is preferably ethyl. Yet another preferred embodiment of said especially preferred group of compounds of formula I-2 comprises compounds wherein A is preferably CH, X2 is preferably SO2 and R12 is preferably ethyl.

In compounds of formula I-2 and all of the preferred embodiments of compounds of formula I-2 mentioned above, G2-2 is preferabl selected from the group consisting of G-0 to G-37:

G-36 G-37

wherein each group G-0 to G-37 is mono-, di- or trisubstituted with Rx, wherein

In compounds of formula I-2 and all of the preferred embodiments of compounds of formula I-2 mentioned above, G2-2 is even more referabl selected from the rou consisting of

wherein each group G is mono-, di- or trisubstituted with Rx, wherein each Rx is, independently selected from the group consisting of hydrogen, Ci-C4alkyl and Ci-C4haloalkyl.

A further preferred embodiment of the invention comprises compounds of formula I represented by the compounds of formula I-3

wherein

A is N or CH;

Gi3 is N or CR9 in which R9 is as defined above under formula I, in particular N or CH;

-3 is selected from the group consistin of

wherein each group G is mono-, di- or trisubstituted with Rx, wherein each Rx is, independently selected from the group consisting of hydrogen, Ci-C4alkyl and Ci-C4haloalkyl, in particular hydrogen, methyl and trifluoromethyl;

X3 is S, SO or SO2, in particular S or SO2, preferably SO2;

Qa3 is selected from the group consisting of Ci-C6haloalkyl, in particular trifluoromethyl;

Ri3 is Ci-C4alkyl, in particular methyl or ethyl; and

Re is Ci-C4alkyl, in particular methyl or ethyl; and agrochemically acceptable salts, stereoisomers, enantiomers, tautomers and N-oxides of the compounds of formula I-3.

In said preferred embodiment comprising compounds of formula I-3, G2-3 is preferably selected from the roup consisting of

wherein each Rx is, independently selected from the group consisting of hydrogen, Ci-C4alkyl and Ci C4haloalkyl, preferably from hydrogen, methyl and trifluoromethyl.

An especially preferred embodiment of the invention comprises compounds of formula I represented by the compounds of formula I-4

wherein

A is N;

G2-4 is selected from the group consisting of

wherein each Rx is, independently selected from the group consisting of hydrogen, Ci-C4alkyl and Ci C4haloalkyl, preferably from hydrogen, methyl and trifluoromethyl; and

Qa4 is Ci-C6haloalkyl, in particular trifluoromethyl;

and agrochemically acceptable salts, stereoisomers, enantiomers, tautomers and N-oxides of the compounds of formula I-4.

In an outstanding group of compounds of formula I ,

R7 is Qi; wherein A is N; X is S or SO2; Ri is Ci-C4alkyl; Q is is Ci-C6haloalkyl;

Re is methyl;

Gi is nitrogen or CR9; wherein R9 is hydrogen; G2 is a pyrazolyl, imidazolyl, isoxazolyl, pyrrolidinyl, triazolyl or thienyl group, each of said groups can be mono- or disubstituted by substituents selected from the group consisting of Ci-C4alkyl and Ci- C4haloalkyl. The process according to the invention for preparing compounds of formula I is carried out in principle by methods known to those skilled in the art. More specifically, the subgroup of compounds of formula I, wherein X is SO (sulfoxide) and/or SO2 (sulfone), may be obtained by means of an oxidation reaction of the corresponding sulfide compounds of formula I, wherein X is S, involving reagents such as, for example, m-chloroperoxybenzoic acid (mCPBA), hydrogen peroxide, oxone, sodium periodate, sodium hypochlorite or tert-butyl hypochlorite amongst other oxidants. The oxidation reaction is generally conducted in the presence of a solvent. Examples of the solvent to be used in the reaction include aliphatic halogenated hydrocarbons such as dichloromethane and chloroform; alcohols such as methanol and ethanol; acetic acid; water; and mixtures thereof. The amount of the oxidant to be used in the reaction is generally 1 to 3 moles, preferably 1 to 1 .2 moles, relative to 1 mole of the sulfide compounds I to produce the sulfoxide compounds I, and preferably 2 to 2.2 moles of oxidant, relative to 1 mole of of the sulfide compounds I to produce the sulfone compounds I. Such oxidation reactions are disclosed, for example, in WO 2013/018928.

Compounds of formula I, wherein G2 is a ring system linked via a carbon atom to the imidazole or triazole ring which contains the group Gi , and wherein R7, Rs, Gi and G2 are as defined above,

II III I

may be prepared by reacting a compound of formula II, wherein G2 is as defined above, and wherein R" is for example hydrogen (in that case the compound of the formula II is a boronic acid) or Ci-C4alkyl (boronic ester), with a compound of formula III, wherein R7, Rs and Gi are as defined above and wherein LG is a halogen, preferably bromine or iodine, or a pseudohalogen such as Ci-4haloalkyl- sulfonate, especially triflate, by means of a transition metal-catalyzed reaction. Indeed, the boronic acid of the formula II, or a suitable salt or ester thereof, will react with a compound of the formula III under palladium- or nickel-catalyzed conditions, such as for example the Suzuki-Miyaura conditions. Such cross coupling reactions are carried out in the presence of a base, such as sodium, potassium or cesium carbonate, in an inert solvent, such as tetrahydrofuran, Ν,Ν-dimethylformamide, dioxane or 1 ,2-dimethoxyethane, or such as 1 ,2-dimethoxyethane-water mixtures, at temperatures between 25- 200°C, preferably 50-150°C, optionally under microwave irradiation. A variety of metals, catalysts and ligands may be used in this reaction type, such as for example [1 , 1-bis(diphenylphosphino)ferrocene] dichloropalladium(ll) (PdCl2(dppf)), tetrakis(triphenylphosphine)palladium(0) (Pd(PPfi3)4) or bis(triphenylphosphine)palladium(ll) dichloride (PdCl2(PPh3)2). Reaction conditions and catalytic systems for such a transformation have been described, for example, in WO08/071405. Alternative boron-based reagents of the formula type II may include boronic esters (also named boronate esters) derived from 2,3-dimethyl-2,3-butanediol (lla), 2,2-dimethyl-1 ,3-propanediol (lib), and 1 ,3-propanediol (lie), and salt analogues of II, such as organotrifluoroborates, for example potassium trifluoroborate salts (lid).

lla lib He lid

Alternatively, compounds of formula I, wherein R7, Rs, Gi and G2 are as defined above,

I may be prepared by a Stille reaction between compound of formula III, wherein R7, Rs and Gi are as defined above and wherein LG is a halogen, preferably bromine or iodine, or a pseudohalogen such as Ci-4haloalkylsulfonate, especially triflate, and compounds of formula Me, wherein G2 are as defined above, and wherein R'" is Ci-C4alkyl. The trialkyl tin functionality -Sn(R"')3 is preferably tri-n-butyl tin or tri-methyl-tin. Such Stille reactions are usually carried out in the presence of a palladium catalyst, for example tetrakis(triphenylphosphine)palladium(0), or bis(triphenylphosphine)palladium(ll) dichloride, in an inert solvent such as Ν,Ν-dimethylformamide, acetonitrile, toluene or dioxane, optionally in the presence of an additive, such as cesium fluoride, or lithium chloride, and optionally in the presence of a further catalyst, for example copper(l)iodide. Such Stille couplings are also well known to those skilled in the art, and have been described in for example J. Org. Chem., 2005, 70, 8601-8604, J. Org. Chem., 2009 , 74, 5599-5602, and Angew. Chem. Int. Ed., 2004, 43, 1 132-1 136.

Compounds of formula Ilia

Ilia

wherein Re and R7 are as defined under formula I above, and wherein LG is a halogen, preferably bromine or iodine, and wherein Gi is N or C-R9 (wherein R9 is as defined under formula I above), preferably N or CH, are novel and especially developed for the preparation of the compounds of formula I of this invention. The compounds of formula Ilia therefore constitute a further object of the invention. The preferred substituent definitions for the compounds of formula I are also valid for the compounds of formula Ilia.

Compounds of formula II I, wherein R7, Rs and Gi are as defined above and wherein LG is a halogen, preferably bromine or iodine,

IV III may be prepared by reacting a compound of formula IV, wherein R7, Rs and Gi are as defined above, with a reagent such as N-chlorosuccinimide (NCS), N-bromosuccinimide (NBS) or N-iodosuccinimide (NIS), or alternatively chlorine, bromine or iodine. Such halogenation reactions are carried out in an inert solvent, such as chloroform, carbon tetrachloride, 1 ,2-dichloroethane, acetic acid, ethers, acetonitrile or Ν,Ν-dimethylformamide, at temperatures between 25-200°C, preferably 25-100°C, as described, for example, in K.G. Holden et al., J. Org. Chem. 2002, 67, 5913-5918.

Compounds of formula IVa

wherein Re and R7 are as defined under formula I above, and wherein Gi is N or C-R9 (wherein R9 is as defined under formula I above), preferably N or CH, are novel and especially developed for the preparation of the compounds of formula I of this invention. The compounds of formula IVa therefore constitute a further object of the invention. The preferred substituent definitions for the compounds of formula I are also valid for the compounds of formula IVa.

The subgroup of compounds of formula III and IV, wherein R7, Rs and Gi are as defined above and wherein X is SO (sulfoxide) and/or SO2 (sulfone), may be obtained by means of an oxidation reaction of the corresponding sulfide compounds of formula III or IV, wherein X is S (sulfide), involving reagents such as, for example, m-chloroperoxybenzoic acid (mCPBA), hydrogen peroxide, oxone, sodium periodate, sodium hypochlorite or tert-butyl hypochlorite amongst other oxidants. The oxidation reaction is generally conducted in the presence of a solvent. Examples of the solvent to be used in the reaction include aliphatic halogenated hydrocarbons such as dichloromethane and chloroform;

alcohols such as methanol and ethanol; acetic acid; water; and mixtures thereof. The amount of the oxidant to be used in the reaction is generally 1 to 3 moles, preferably 1 to 1.2 moles, relative to 1 mole of the sulfide compounds III or IV to produce the sulfoxide compounds III or IV, and preferably 2 to 2.2 moles of oxidant, relative to 1 mole of of the sulfide compounds III or IV to produce the sulfone compounds III or IV. Such oxidation reactions are disclosed, for example, in WO 2013/018928.

Compounds of formula IV, wherein R7, Rs and Gi are as defined above and wherein X is S (sulfide), can be prepared by reacting a compound of formula V

wherein Rs and Gi are as described in formula I and wherein Rza is a radical selected from the group consisting of formula Qi_a to Ctea:

wherein A and Q are as defined above, and wherein X10 is a halogen (preferably fluorine, chlorine bromine), with a compound of formula VI

or a salt thereof, wherein Ri is as defined in formula I, optionally in the presence of a suitable base, such as alkali metal carbonates, for example sodium carbonate and potassium carbonate, or alkali metal hydrides such as sodium hydride, or alkali metal hydroxides such as sodium hydroxide and potassium hydroxide, in an inert solvent at temperatures preferably between 25-120°C. Examples of solvent to be used include ethers such as THF, ethylene glycol dimethyl ether, tert-butylmethyl ether, and 1 ,4-dioxane, aromatic hydrocarbons such as toluene and xylene, nitriles such as acetonitrile or polar aprotic solvents such as N,N-dimethylformamide, Ν,Ν-dimethylacetamide, N-methyl-2- pyrrolidone or dimethyl sulfoxide. Examples of salts of the compound of formula VI include compounds of the formula Via

wherein Ri is as defined above and wherein M is, for example, sodium or potassium.

Alternatively, compounds of formula I may be prepared from compounds of formula V involving the same chemistry as described above, but by changing the order of the steps. This alternative route is summarized below:

wherein R7 is selected from Qi to Q2 wherein R7 is selected from Qi to Q2 and in which X is S (sulfide) and in which X is SO or SO2

Compounds of formula I, wherein G2 is a ring system linked via a nitrogen atom to the imidazole or triazole ring which contains the group Gi (i.e. where G2 is a nitrogen containing heteroring system), and wherein R7, Rs, Gi and G2 are as defined above,

may be prepared by reacting a compound of formula ll-(NH), or a tautomer thereof and/or a salt thereof (such as a hydrohalide salt, preferably a hydrochloride or a hydrobromide salt, or any other equivalent salt), wherein the entity G2 (NH) is a nitrogen containing heteroring system that contains an appropriate NH functionality and in which a nitrogen atom becomes the attachment point to the imidazole or triazole ring which contains the group Gi, and wherein G2 as defined above, with a compound of formula III, wherein R7, Rs and Gi are as defined above and wherein LG is a halogen, preferably bromine or iodine, or a pseudohalogen such as Ci-4haloalkylsulfonate, especially triflate, by means of a base mediated N-hetarylation reaction. This reaction includes bases such as, for example, sodium hydride or alkali metal carbonates like sodium carbonate, potassium carbonate, cesium carbonate or tetraethylammonium carbonate, or potassium phosphate, triethylamine or pyridine, and is conducted in solvents such as nitrobenzene, dioxane, acetonitrile, toluene, dimethylsulfoxide, N- methylpyrrolidone, A/,A/-dimethylformamide or A/,A/-dimethylacetamide, where appropriate with water as co-solvent, and at temperatures between 0-300°C, preferably at 50-250°C, with optional use of microwave heating. Optionally the reaction may be transition metal mediated, or preferably catalyzed by transition metals, such as, for example, metalic copper or copper(l) salts, especially copper(l) halides like copper(l) chloride, copper(l) bromide, copper(l) iodide or copper(l) oxide (especially preferred is copper(l) iodide), or copper(ll) salts, like for example copper(ll) acetate. Optional additives such as diamine ligands (preferably 1 , 10-phenanthroline, 1 ,2-ethanediamine, A/,A/'-dimethyl-1 ,2- ethanediamine, A/,A/-dimethyl-1 ,2-ethanediamine, 1 ,2-cyclohexanediamine or Λ/,Λ/'-dimethyl- cyclohexane-1 ,2-diamine) or 8-quinolinol, glycine, dimethylglycine or proline may be used in this N- hetarylation reaction. Such reactions are further illustrated in, for example, WO201 1/017504, Liu et al., J. Org. Chem. 2005, 70, 10135-10138 or Antilla et al., J. Org. Chem. 2004, 69, 5578-5587.

Such a N-hetarylation reaction is illustrated below for the heterocycle G2 (NH) being specifically G-29, wherein G-29 and R_x are as defined above, to give a compound of formula l-(G-29), a particular subgroup of compounds of formula I, wherein R_x, Gi , R7 and Re are as previously defined.

Compounds of formula ll-(NH), or a tautomer thereof and/or a salt thereof (such as a hydrohalide salt, preferably a hydrochloride or a hydrobromide salt, or any other equivalent salt), wherein G2 as defined above, are known compounds, commercial compounds or can be prepared by known methods, described in the literature. The subgroup of compounds of formula V, wherein Rza and Re are as defined above and wherein Gi is defined as CR9, in which R9 is as defined above, may be defined as compounds of formula V-G1-I .

Compounds of formula V-G1-I, wherein Re, R9 and Rza are as defined above, can be prepared by reacting a compound of formula VII and/or a tautomer thereof. The described process to prepare compounds of the formula VII from compounds of the formula IX may include isolation and purification of the intermediates ΙΝΤΊ and INT2, (which may be isolated as free bases or as salts (e.g. a hydrohalide salt, more specifically a hydrochloride or hydrobromide salt, or any other equivalent salt)), however, this process is advantageously conducted as a one-pot preparation as described, for example, in M.E. Voss et al., Tetrahedron 2008, 64, 645-651. The process is summarized below for the particular situation where R9 is hydrogen:

Compounds of the formula INT1 may alternatively be prepared under conditions and variants of the Pinner reaction known to a person skilled in the art, typically by treating a compound of the formula IX with a hydrohalide acid, preferably hydrochloric acid, in presence of alcoholic reagents such as methanol or ethanol, preferably in an inert solvent such as diethyl ether, tetrahydrofuran or dioxane, at temperatures between -40 and 50°C, preferably between -20 and 20°C. Compounds of formula IX, wherein Rza is as described above and reagents of formula XI, wherein F¾ and R^IV are as described above, are known compounds or can be prepared by known methods, described in the literature. The subgroup of compounds of formula V, wherein Rza and Re are as defined above and wherein Gi is defined as N (nitrogen), may be defined as compounds of formula V-G1-T.

may be prepared by reacting a compound of formula XII, or a tautomer thereof, wherein Re and Rza are as defined above, with an oxidant such as nitric acid, in the presence of water, optionally in the presence of an inert co-solvent, at temperatures preferably between 25-180°C. Such an oxidative desulfurization process of a 1 ,2,4-triazole thione compound of the formula XII, which involves loss of sulfur dioxide (SO2 gas evolution) from an intermediate sulfinic acid, is described, for example, in J.M. Kane et al., J. Heterocyclic Chem. 1995, 32, 183-87. Compounds of formula XII, or a tautomer thereof, wherein Re and Rza are as defined above,

may be prepared by reacting a compound of formula XIII, wherein Re and Rza are as defined above, in the presence of a base, such as sodium, potassium or cesium carbonate, sodium or potassium hydrogen carbonate, tripotassium phosphate, sodium or potassium hydroxide, in an inert solvent, such as water, dioxane, methanol or ethanol, or mixtures thereof, at temperatures between 25-200°C, preferably 50-150°C, optionally under microwave irradiation, as described, for example, in

ChemMedChem, 8(6), 994-1001 , 2013 and Farmaco, Edizione Scientifica, 36(3), 181-96, 1981 .

Compounds of formula XIII may exist as different tautomeric forms, or in mixtures thereof. Description in the literature about such thione-thiol tautomeric forms may be found, for example, in Chem. Pharm. Bull. 1973, 21 , 1342-1350.

Compounds of formula XIII, wherein Re and Rza are as defined above,

XXVIII

may be prepared by i) activation of a compound of formula XIV, wherein Rza is as defined above, by methods known to those skilled in the art and described in, for example, Tetrahedron, 2005, 61 (46), 10827-10852, to form an activated species XlVa, wherein Rza is as defined above and wherein Xoo is halogen, preferably chlorine. For example, compounds XlVa where Xoo is halogen, preferably chlorine, are formed by treatment of XIV with, for example, oxallyl chloride (COCI)2 or thionyl chloride SOCI2 in the presence of catalytic quantities of Ν,Ν-dimethylformamide DMF in inert solvents such as methylene chloride CH2CI2 or tetrahydrofuran THF at temperatures between 20 to 100°C, preferably 25°C.

Alternatively, treatment of compounds of formula XIV with, for example, 1-ethyl-3-(3-dimethylamino- propyl)carbodiimide EDC or dicyclohexyl carbodiimide DCC will generate an activated species XlVa, wherein Xoo is X01 or X02 respectively, in an inert solvent, such as pyridine or tetrahydrofuran THF, optionally in the presence of a base, such as triethylamine, at temperatures between 50-180°C;

followed by

ii) treament of the activated species XlVa with a thiosemicarbazide compound of formula XV (or a salt thereof), wherein Re is as defined above, optionally in the presence of a base, such as triethylamine or pyridine, in an inert solvents such as dichloromethane, tetrahydrofuran, dioxane or toluene, at temperatures between 0 and 50°C, to form the compounds of formula XIII, as described, for example, in J. Med. Chem. 1994, 37, 125-132. Certain bases, such as pyridine and triethylamine, may be employed successfully as both base and solvent. Alternatively, compounds of the formula XIII, wherein Re and Rza are as defined above, may be prepared by reacting a hydrazide compound of formula XVII, wherein Rza is as defined above, with an isothiocyanate reagent of the formula XIX, wherein Re is as defined above, in an inert solvent, such as tetrahydrofuran, dioxane, methanol, ethanol, acetonitrile or Ν,Ν-dimethylformamide, at temperatures between 25-200°C, preferably 50-150°C, optionally under microwave irradiation, as described, for example, in J. Med. Chem. 1994, 37, 125-132.

Compounds of the formula XVII, or a salt thereof, wherein Rza is as defined above, may be prepared by either the direct action of hydrazine XVIII (or a salt thereof), possibly in form of a hydrate, preferably hydrazine monohydrate, on an ester derivative XlVb of the compound of formula XIV, wherein Rza is as defined above and wherein Roo is Ci-C4alkyl, preferably methyl or ethyl, at temperatures between 20 and 150°C, optionally under microwave irradiation. Such a process description may be found, for example, in M.H. Klingele et al, Eur.J. Org. Chem. 2004, 3422-3434. Alternatively, treament of the activated species XlVa with hydrazine XVIII (or a salt thereof), possibly in form of a hydrate, preferably hydrazine monohydrate, optionally in the presence of a base, such as triethylamine or pyridine, in an inert solvents such as dichloromethane, tetrahydrofuran, dioxane or toluene, at temperatures between 0 and 50°C, will also form the compounds of formula XVII.

Esters of formula XlVb, wherein Rza is as defined above and wherein Roo is Ci-C4alkyl, preferably methyl or ethyl, may be prepared by either the direct action of an alcohol Roo-OH of formula XVI, wherein Roo is Ci-C4alkyl, on compounds of formula XlVa, wherein Rza is as defined above, or by means of an esterification reaction of compounds of formula XIV with an alcohol Roo-OH of formula XVI, wherein Roo is Ci-C4alkyl, in the presence of a catalytic amount of an acid, such as hydrochloric acid HCI or sulfuric acid H2SO4, under refluxing conditions. Both of these methods are well known to a person skilled in the art and precedented in the literature.

Compounds of formula XIV and XlVb, wherein Rza is as defined above and wherein Roo is Ci-C4alkyl, are known compounds or can be prepared by known methods, described in the literature. Reagents of formula XV and XIX, wherein Re is as defined above, are known compounds or can be prepared by known methods, described in the literature.

The reactants can be reacted in the presence of a base. Examples of suitable bases are alkali metal or alkaline earth metal hydroxides, alkali metal or alkaline earth metal hydrides, alkali metal or alkaline earth metal amides, alkali metal or alkaline earth metal alkoxides, alkali metal or alkaline earth metal acetates, alkali metal or alkaline earth metal carbonates, alkali metal or alkaline earth metal dialkylamides or alkali metal or alkaline earth metal alkylsilylamides, alkylamines, alkylenediamines, free or N-alkylated saturated or unsaturated cycloalkylamines, basic heterocycles, ammonium hydroxides and carbocyclic amines. Examples which may be mentioned are sodium hydroxide, sodium hydride, sodium amide, sodium methoxide, sodium acetate, sodium carbonate, potassium tert- butoxide, potassium hydroxide, potassium carbonate, potassium hydride, lithium diisopropylamide, potassium bis(trimethylsilyl)amide, calcium hydride, triethylamine, diisopropylethylamine,

triethylenediamine, cyclohexylamine, N-cyclohexyl-N,N-dimethylamine, Ν,Ν-diethylaniline, pyridine, 4- (N,N-dimethylamino)pyridine, quinuclidine, N-methylmorpholine, benzyltrimethylammonium hydroxide and 1 ,8-diazabicyclo[5.4.0]undec-7-ene (DBU). The reactants can be reacted with each other as such, i.e. without adding a solvent or diluent. In most cases, however, it is advantageous to add an inert solvent or diluent or a mixture of these. If the reaction is carried out in the presence of a base, bases which are employed in excess, such as triethylamine, pyridine, N-methylmorpholine or Ν,Ν-diethylaniline, may also act as solvents or diluents. The reaction is advantageously carried out in a temperature range from approximately -80°C to approximately +140°C, preferably from approximately -30°C to approximately +100°C, in many cases in the range between ambient temperature and approximately +80°C.

A compound of formula I can be converted in a manner known per se into another compound of formula I by replacing one or more substituents of the starting compound of formula I in the customary manner by (an)other substituent(s) according to the invention.

Depending on the choice of the reaction conditions and starting materials which are suitable in each case, it is possible, for example, in one reaction step only to replace one substituent by another substituent according to the invention, or a plurality of substituents can be replaced by other substituents according to the invention in the same reaction step.

Salts of compounds of formula I can be prepared in a manner known per se. Thus, for example, acid addition salts of compounds of formula I are obtained by treatment with a suitable acid or a suitable ion exchanger reagent and salts with bases are obtained by treatment with a suitable base or with a suitable ion exchanger reagent.

Salts of compounds of formula I can be converted in the customary manner into the free compounds I, acid addition salts, for example, by treatment with a suitable basic compound or with a suitable ion exchanger reagent and salts with bases, for example, by treatment with a suitable acid or with a suitable ion exchanger reagent.

Salts of compounds of formula I can be converted in a manner known per se into other salts of compounds of formula I, acid addition salts, for example, into other acid addition salts, for example by treatment of a salt of inorganic acid such as hydrochloride with a suitable metal salt such as a sodium, barium or silver salt, of an acid, for example with silver acetate, in a suitable solvent in which an inorganic salt which forms, for example silver chloride, is insoluble and thus precipitates from the reaction mixture.

Depending on the procedure or the reaction conditions, the compounds of formula I, which have salt- forming properties can be obtained in free form or in the form of salts.

The compounds of formula I and, where appropriate, the tautomers thereof, in each case in free form or in salt form, can be present in the form of one of the isomers which are possible or as a mixture of these, for example in the form of pure isomers, such as antipodes and/or diastereomers, or as isomer mixtures, such as enantiomer mixtures, for example racemates, diastereomer mixtures or racemate mixtures, depending on the number, absolute and relative configuration of asymmetric carbon atoms which occur in the molecule and/or depending on the configuration of non-aromatic double bonds which occur in the molecule; the invention relates to the pure isomers and also to all isomer mixtures which are possible and is to be understood in each case in this sense hereinabove and hereinbelow, even when stereochemical details are not mentioned specifically in each case.

Diastereomer mixtures or racemate mixtures of compounds of formula I, in free form or in salt form, which can be obtained depending on which starting materials and procedures have been chosen can be separated in a known manner into the pure diasteromers or racemates on the basis of the physicochemical differences of the components, for example by fractional crystallization, distillation and/or chromatography. Enantiomer mixtures, such as racemates, which can be obtained in a similar manner can be resolved into the optical antipodes by known methods, for example by recrystallization from an optically active solvent, by chromatography on chiral adsorbents, for example high-performance liquid

chromatography (HPLC) on acetyl celulose, with the aid of suitable microorganisms, by cleavage with specific, immobilized enzymes, via the formation of inclusion compounds, for example using chiral crown ethers, where only one enantiomer is complexed, or by conversion into diastereomeric salts, for example by reacting a basic end-product racemate with an optically active acid, such as a carboxylic acid, for example camphor, tartaric or malic acid, or sulfonic acid, for example camphorsulfonic acid, and separating the diastereomer mixture which can be obtained in this manner, for example by fractional crystallization based on their differing solubilities, to give the diastereomers, from which the desired enantiomer can be set free by the action of suitable agents, for example basic agents.

Pure diastereomers or enantiomers can be obtained according to the invention not only by separating suitable isomer mixtures, but also by generally known methods of diastereoselective or

enantioselective synthesis, for example by carrying out the process according to the invention with starting materials of a suitable stereochemistry.

N-oxides can be prepared by reacting a compound of the formula I with a suitable oxidizing agent, for example the hbCh/urea adduct in the presence of an acid anhydride, e.g. trifluoroacetic anhydride. Such oxidations are known from the literature, for example from J. Med. Chem., 32 (12), 2561-73, 1989 or WO 00/15615.

It is advantageous to isolate or synthesize in each case the biologically more effective isomer, for example enantiomer or diastereomer, or isomer mixture, for example enantiomer mixture or diastereomer mixture, if the individual components have a different biological activity.

The compounds of formula I and, where appropriate, the tautomers thereof, in each case in free form or in salt form, can, if appropriate, also be obtained in the form of hydrates and/or include other solvents, for example those which may have been used for the crystallization of compounds which are present in solid form.

The compounds according to the following Tables 1 to 12 below can be prepared according to the methods described above. The examples which follow are intended to illustrate the invention and show preferred compounds of formula I.

Table 1 : This table discloses the 1 1 compounds 1 .001 to 1.01 1 of the formula l-1a:

wherein Xi is S, and QR_x, Rn, A and G2 are as defined below: Table 1:

and the N-oxides of the compounds of Table 1. Where indicated, the arrow denotes the point of attachement to the triazole ring.

Table 2: This table discloses the 1 1 compounds 2.001 to 2.01 1 of the formula l-1a, wherein Xi is SO, and QRX, R11 , A and G2 are as defined in Table 1.

Table 3: This table discloses the 1 1 compounds 3.001 to 3.01 1 of the formula l-1a, wherein Xi is SO2, and QRX, R11 , A and G2 are as defined in Table 1.

Table 4: This table discloses one compound 4.005 of the formula l-2a:

wherein X2 is S, and QR_X, R12, A and G2 are as defined below: Table 4:

and the N-oxides of the compound of Table 4. Where indicated, the arrow denotes the point of attachement to the triazole ring.

Table 5: This table discloses one compound 5.005 of the formula l-2a, wherein X2 is SO, and QR_X, R12, A and G2 are as defined in Table 4.

Table 6: This table discloses one compound 6.005 of the formula l-2a, wherein X2 is SO2, and QR_X, R12, A and G2 are as defined in Table 4.

Table 7: This table discloses the 1 1 compounds 7.001 to 7.01 1 of the formula l-3a:

wherein X3 is S, and QR_X, R13, A and G2 are as defined below:

Table 7:

an e -ox es of e compoun s of a e . ere n cae , e arrow enoes the point of attachement to the triazole ring.

Table 8: This table discloses the 11 compounds 8.001 to 8.011 of the formula l-3a, wherein X3 is SO, and QRX, Ri3, A and G2 are as defined in Table 7.

Table 9: This table discloses the 11 compounds 9.001 to 9.011 of the formula l-3a, wherein X3 is SO2, and QRX, Ri3, A and G2 are as defined in Table 7.

Table 10: This table discloses one compound 10.005 of the formula l-4a:

wherein X4 is S, and QR_X, R14, A and G2 are as defined below: Table 10:

and the N-oxides of the compound of Table 10. Where indicated, the arrow denotes the point of attachement to the triazole ring.

Table 1 1 : This table discloses one compound 1 1 .005 of the formula l-4a, wherein X4 is SO, and QR_X, Ri4, A and G2 are as defined in Table 10.

Table 12: This table discloses one compound 12.005 of the formula l-4a, wherein X4 is SO2, and QR_X, Ri4, A and G2 are as defined in Table 10. The compounds of formula I according to the invention are preventively and/or curatively valuable active ingredients in the field of pest control, even at low rates of application, which have a very favorable biocidal spectrum and are well tolerated by warm-blooded species, fish and plants. The active ingredients according to the invention act against all or individual developmental stages of normally sensitive, but also resistant, animal pests, such as insects or representatives of the order Acarina. The insecticidal or acaricidal activity of the active ingredients according to the invention can manifest itself directly, i. e. in destruction of the pests, which takes place either immediately or only after some time has elapsed, for example during ecdysis, or indirectly, for example in a reduced oviposition and/or hatching rate, a good activity corresponding to a destruction rate (mortality) of at least 50 to 60%. Examples of the abovementioned animal pests are:

from the order Acarina, for example,

Acalitus spp, Aculus spp, Acaricalus spp, Aceria spp, Acarus siro, Amblyomma spp., Argas spp., Boophilus spp., Brevipalpus spp., Bryobia spp, Calipitrimerus spp., Chorioptes spp., Dermanyssus gallinae, Dermatophagoides spp, Eotetranychus spp, Eriophyes spp., Hemitarsonemus spp,

Hyalomma spp., Ixodes spp., Olygonychus spp, Ornithodoros spp., Polyphagotarsone latus,

Panonychus spp., Phyllocoptruta oleivora, Phytonemus spp, Polyphagotarsonemus spp, Psoroptes spp., Rhipicephalus spp., Rhizoglyphus spp., Sarcoptes spp., Steneotarsonemus spp, Tarsonemus spp. and Tetranychus spp.;

from the order Anoplura, for example,

Haematopinus spp., Linognathus spp., Pediculus spp., Pemphigus spp. and Phylloxera spp.;

from the order Coleoptera, for example,

Agriotes spp., Amphimallon majale, Anomala orientalis, Anthonomus spp., Aphodius spp, Astylus atromaculatus, Ataenius spp, Atomaria linearis, Chaetocnema tibialis, Cerotoma spp, Conoderus spp, Cosmopolites spp., Cotinis nitida, Curculio spp., Cyclocephala spp, Dermestes spp., Diabrotica spp., Diloboderus abderus, Epilachna spp., Eremnus spp., Heteronychus arator, Hypothenemus hampei, Lagria vilosa, Leptinotarsa decemLineata, Lissorhoptrus spp., Liogenys spp, Maecolaspis spp, Maladera castanea, Megascelis spp, Melighetes aeneus, Melolontha spp., Myochrous armatus, Orycaephilus spp., Otiorhynchus spp., Phyllophaga spp, Phlyctinus spp., Popillia spp., Psylliodes spp., Rhyssomatus aubtilis, Rhizopertha spp., Scarabeidae, Sitophilus spp., Sitotroga spp., Somaticus spp, Sphenophorus spp, Sternechus subsignatus, Tenebrio spp., Tribolium spp. and Trogoderma spp.; from the order Diptera, for example,

Aedes spp., Anopheles spp, Antherigona soccata,Bactrocea oleae, Bibio hortulanus, Bradysia spp, Calliphora erythrocephala, Ceratitis spp., Chrysomyia spp., Culex spp., Cuterebra spp., Dacus spp., Delia spp, Drosophila melanogaster, Fannia spp., Gastrophilus spp., Geomyza tripunctata, Glossina spp., Hypoderma spp., Hyppobosca spp., Liriomyza spp., Lucilia spp., Melanagromyza spp., Musca spp., Oestrus spp., Orseolia spp., Oscinella frit, Pegomyia hyoscyami, Phorbia spp., Rhagoletis spp, Rivelia quadrifasciata, Scatella spp, Sciara spp., Stomoxys spp., Tabanus spp., Tannia spp. and Tipula spp.;

from the order Hemiptera, for example,

Acanthocoris scabrator, Acrosternum spp, Adelphocoris lineolatus, Amblypelta nitida, Bathycoelia thalassina, Blissus spp, Cimex spp., Clavigralla tomentosicollis, Creontiades spp, Distantiella theobroma, Dichelops furcatus, Dysdercus spp., Edessa spp, Euchistus spp., Eurydema pulchrum, Eurygaster spp., Halyomorpha halys, Horcias nobilellus, Leptocorisa spp., Lygus spp, Margarodes spp, Murgantia histrionic, Neomegalotomus spp, Nesidiocoris tenuis, Nezara spp., Nysius simulans, Oebalus insularis, Piesma spp., Piezodorus spp, Rhodnius spp., Sahlbergella singularis, Scaptocoris castanea, Scotinophara spp. , Thyanta spp , Triatoma spp., Vatiga illudens;

Acyrthosium pisum, Adalges spp, Agalliana ensigera, Agonoscena targionii, Aleurodicus spp, Aleurocanthus spp, Aleurolobus barodensis, Aleurothrixus floccosus, Aleyrodes brassicae, Amarasca biguttula, Amritodus atkinsoni, Aonidiella spp., Aphididae, Aphis spp., Aspidiotus spp., Aulacorthum solani, Bactericera cockerelli, Bemisia spp, Brachycaudus spp, Brevicoryne brassicae, Cacopsylla spp, Cavariella aegopodii Scop., Ceroplaster spp., Chrysomphalus aonidium, Chrysomphalus dictyospermi, Cicadella spp, Cofana spectra, Cryptomyzus spp, Cicadulina spp, Coccus hesperidum, Dalbulus maidis, Dialeurodes spp, Diaphorina citri, Diuraphis noxia, Dysaphis spp, Empoasca spp., Eriosoma larigerum, Erythroneura spp., Gascardia spp., Glycaspis brimblecombei, Hyadaphis pseudobrassicae, Hyalopterus spp, Hyperomyzus pallidus, Idioscopus clypealis, Jacobiasca lybica, Laodelphax spp., Lecanium corni, Lepidosaphes spp., Lopaphis erysimi, Lyogenys maidis,

Macrosiphum spp., Mahanarva spp, Metcalfa pruinosa, Metopolophium dirhodum, Myndus crudus, Myzus spp., Neotoxoptera sp, Nephotettix spp., Nilaparvata spp., Nippolachnus piri Mats, Odonaspis ruthae, Oregma lanigera Zehnter, Parabemisia myricae, Paratrioza cockerelli, Parlatoria spp., Pemphigus spp., Peregrinus maidis, Perkinsiella spp, Phorodon humuli, Phylloxera spp, Planococcus spp., Pseudaulacaspis spp., Pseudococcus spp., Pseudatomoscelis seriatus, Psylla spp., Pulvinaria aethiopica, Quadraspidiotus spp., Quesada gigas, Recilia dorsalis, Rhopalosiphum spp., Saissetia spp., Scaphoideus spp., Schizaphis spp., Sitobion spp., Sogatella furcifera, Spissistilus festinus, Tarophagus Proserpina, Toxoptera spp, Trialeurodes spp, Tridiscus sporoboli, Trionymus spp, Trioza erytreae , Unaspis citri, Zygina flammigera, Zyginidia scutellaris, ;

from the order Hymenoptera, for example,

Acromyrmex, Arge spp, Atta spp., Cephus spp., Diprion spp., Diprionidae, Gilpinia polytoma, Hoplo- campa spp., Lasius spp., Monomorium pharaonis, Neodiprion spp., Pogonomyrmex spp, Slenopsis invicta, Solenopsis spp. and Vespa spp.;

from the order Isoptera, for example,

Coptotermes spp, Corniternes cumulans, Incisitermes spp, Macrotermes spp, Mastotermes spp, Microtermes spp, Reticulitermes spp.; Solenopsis geminate

from the order Lepidoptera, for example,

Acleris spp., Adoxophyes spp., Aegeria spp., Agrotis spp., Alabama argillaceae, Amylois spp., Anticarsia gemmatalis, Archips spp., Argyresthia spp, Argyrotaenia spp., Autographa spp., Bucculatrix thurberiella, Busseola fusca, Cadra cautella, Carposina nipponensis, Chilo spp., Choristoneura spp., Chrysoteuchia topiaria, Clysia ambiguella, Cnaphalocrocis spp., Cnephasia spp., Cochylis spp.,

Coleophora spp., Colias lesbia, Cosmophila flava, Crambus spp, Crocidolomia binotalis, Cryptophlebia leucotreta, Cydalima perspectalis, Cydia spp., Diaphania perspectalis, Diatraea spp., Diparopsis castanea, Earias spp., Eldana saccharina, Ephestia spp., Epinotia spp, Estigmene acrea, Etiella zinckinella, Eucosma spp., Eupoecilia ambiguella, Euproctis spp., Euxoa spp., Feltia jaculiferia, Gra- pholita spp., Hedya nubiferana, Heliothis spp., Hellula undalis, Herpetogramma spp, Hyphantria cunea, Keiferia lycopersicella, Lasmopalpus lignosellus, Leucoptera scitella, Lithocollethis spp., Lobesia botrana, Loxostege bifidalis, Lymantria spp., Lyonetia spp., Malacosoma spp., Mamestra brassicae, Manduca sexta, Mythimna spp, Noctua spp, Operophtera spp., Orniodes indica, Ostrinia nubilalis, Pammene spp., Pandemis spp., Panolis flammea, Papaipema nebris, Pectinophora gossypi- ela, Perileucoptera coffeella, Pseudaletia unipuncta, Phthorimaea operculella, Pieris rapae, Pieris spp., Plutella xylostella, Prays spp., Pseudoplusia spp, Rachiplusia nu, Richia albicosta, Scirpophaga spp., Sesamia spp., Sparganothis spp., Spodoptera spp., Sylepta derogate, Synanthedon spp., Thaumetopoea spp., Tortrix spp., Trichoplusia ni, Tuta absoluta, and Yponomeuta spp.;

from the order Mallophaga, for example,

Damalinea spp. and Trichodectes spp.;

from the order Orthoptera, for example,

Blatta spp., Blattella spp., Gryllotalpa spp., Leucophaea maderae, Locusta spp., Neocurtilla hexadactyla, Periplaneta spp. , Scapteriscus spp, and Schistocerca spp.;

from the order Psocoptera, for example,

Liposcelis spp.;

from the order Siphonaptera, for example,

Ceratophyllus spp., Ctenocephalides spp. and Xenopsylla cheopis; from the order Thysanoptera, for example, Calliothrips phaseoli, Frankliniella spp., Heliothrips spp, Hercinothrips spp., Parthenothrips spp, Scirtothrips aurantii, Sericothrips variabilis, Taeniothrips spp., Thrips spp;

from the order Thysanura, for example, Lepisma saccharina. The active ingredients according to the invention can be used for controlling, i. e. containing or destroying, pests of the abovementioned type which occur in particular on plants, especially on useful plants and ornamentals in agriculture, in horticulture and in forests, or on organs, such as fruits, flowers, foliage, stalks, tubers or roots, of such plants, and in some cases even plant organs which are formed at a later point in time remain protected against these pests.

Suitable target crops are, in particular, cereals, such as wheat, barley, rye, oats, rice, maize or sorghum; beet, such as sugar or fodder beet; fruit, for example pomaceous fruit, stone fruit or soft fruit, such as apples, pears, plums, peaches, almonds, cherries or berries, for example strawberries, raspberries or blackberries; leguminous crops, such as beans, lentils, peas or soya; oil crops, such as oilseed rape, mustard, poppies, olives, sunflowers, coconut, castor, cocoa or ground nuts; cucurbits, such as pumpkins, cucumbers or melons; fibre plants, such as cotton, flax, hemp or jute; citrus fruit, such as oranges, lemons, grapefruit or tangerines; vegetables, such as spinach, lettuce, asparagus, cabbages, carrots, onions, tomatoes, potatoes or bell peppers; Lauraceae, such as avocado, Cinnamonium or camphor; and also tobacco, nuts, coffee, eggplants, sugarcane, tea, pepper, grapevines, hops, the plantain family and latex plants.

The compositions and/or methods of the present invention may be also used on any ornamental and/or vegetable crops, including flowers, shrubs, broad-leaved trees and evergreens.

For example the invention may be used on any of the following ornamental species: Ageratum spp., Alonsoa spp., Anemone spp., Anisodontea capsenisis, Anthemis spp., Antirrhinum spp., Aster spp., Begonia spp. (e.g. B. elatior, B. semperflorens, B. tubereux), Bougainvillea spp., Brachycome spp., Brassica spp. (ornamental), Calceolaria spp., Capsicum annuum, Catharanthus roseus, Canna spp., Centaurea spp., Chrysanthemum spp., Cineraria spp. (C. maritime), Coreopsis spp., Crassula coccinea, Cuphea ignea, Dahlia spp., Delphinium spp., Dicentra spectabilis, Dorotheantus spp., Eustoma grandiflorum, Forsythia spp., Fuchsia spp., Geranium gnaphalium, Gerbera spp.,

Gomphrena globosa, Heliotropium spp., Helianthus spp., Hibiscus spp., Hortensia spp., Hydrangea spp., Hypoestes phyllostachya, Impatiens spp. (/. Walleriana), Iresines spp., Kalanchoe spp., Lantana camara, Lavatera trimestris, Leonotis leonurus, Lilium spp., Mesembryanthemum spp., Mimulus spp., Monarda spp., Nemesia spp., Tagetes spp., Dianthus spp. (carnation), Canna spp., Oxalis spp., Bellis spp., Pelargonium spp. (P. peltatum, P. Zonale), Viola spp. (pansy), Petunia spp., Phlox spp.,

Plecthranthus spp., Poinsettia spp., Parthenocissus spp. (P. quinquefolia, P. tricuspidata), Primula spp., Ranunculus spp., Rhododendron spp., Rosa spp. (rose), Rudbeckia spp., Saintpaulia spp., Salvia spp., Scaevola aemola, Schizanthus wisetonensis, Sedum spp., Solanum spp., Surfinia spp., Tagetes spp., Nicotinia spp., Verbena spp., Zinnia spp. and other bedding plants. For example the invention may be used on any of the following vegetable species: Allium spp. (A sativum, A., cepa, A. oschaninii, A. Porrum, A. ascalonicum, A. fistulosum), Anthriscus cerefolium, Apium graveolus, Asparagus officinalis, Beta vulgarus, Brassica spp. (B. Oleracea, B. Pekinensis, B. rapa), Capsicum annuum, Cicer arietinum, Cichorium endivia, Cichorum spp. (C. intybus, C. endivia), Citrillus lanatus, Cucumis spp. (C. sativus, C. melo), Cucurbita spp. (C. pepo, C. maxima), Cyanara spp. (C. scolymus, C. cardunculus), Daucus carota, Foeniculum vulgare, Hypericum spp., Lactuca sativa, Lycopersicon spp. (L. esculentum, L. lycopersicum), Mentha spp., Ocimum basilicum,

Petroselinum crispum, Phaseolus spp. (P. vulgaris, P. coccineus), Pisum sativum, Raphanus sativus, Rheum rhaponticum, Rosemarinus spp., Salvia spp., Scorzonera hispanica, Solanum melongena, Spinacea oleracea, Valerianella spp. (V. locusta, V. eriocarpa) and Vicia faba.

Preferred ornamental species include African violet, Begonia, Dahlia, Gerbera, Hydrangea, Verbena, Rosa, Kalanchoe, Poinsettia, Aster, Centaurea, Coreopsis, Delphinium, Monarda, Phlox, Rudbeckia, Sedum, Petunia, Viola, Impatiens, Geranium, Chrysanthemum, Ranunculus, Fuchsia, Salvia, Hortensia, rosemary, sage, St. Johnswort, mint, sweet pepper, tomato and cucumber. The active ingredients according to the invention are especially suitable for controlling Aphis craccivora, Diabrotica balteata, Heliothis virescens, Myzus persicae, Plutella xylostella and

Spodoptera littoralis in cotton, vegetable, maize, rice and soya crops. The active ingredients according to the invention are further especially suitable for controlling Mamestra (preferably in vegetables), Cydia pomonella (preferably in apples), Empoasca(preferably in vegetables, vineyards), Leptinotarsa (preferably in potatos) and Chilo supressalis (preferably in rice).

In a further aspect, the invention may also relate to a method of controlling damage to plant and parts thereof by plant parasitic nematodes (Endoparasitic-, Semiendoparasitic- and Ectoparasitic nematodes), especially plant parasitic nematodes such as root knot nematodes, Meloidogyne hapla, Meloidogyne incognita, Meloidogyne javanica, Meloidogyne arenaria and other Meloidogyne species; cyst-forming nematodes, Globodera rostochiensis and other Globodera species; Heterodera avenae, Heterodera glycines, Heterodera schachtii, Heterodera trifolii, and other Heterodera species; Seed gall nematodes, Anguina species; Stem and foliar nematodes, Aphelenchoides species; Sting nematodes, Belonolaimus longicaudatus and other Belonolaimus species; Pine nematodes, Bursaphelenchus xylophilus and other Bursaphelenchus species; Ring nematodes, Criconema species, Criconemella species, Criconemoides species, Mesocriconema species; Stem and bulb nematodes, Ditylenchus destructor, Ditylenchus dipsaci and other Ditylenchus species; Awl nematodes, Dolichodorus species; Spiral nematodes, Heliocotylenchus multicinctus and other Helicotylenchus species; Sheath and sheathoid nematodes, Hemicycliophora species and Hemicriconemoides species; Hirshmanniella species; Lance nematodes, Hoploaimus species; false rootknot nematodes, Nacobbus species;

Needle nematodes, Longidorus elongatus and other Longidorus species; Pin nematodes,

Pratylenchus species; Lesion nematodes, Pratylenchus neglectus, Pratylenchus penetrans,

Pratylenchus curvitatus, Pratylenchus goodeyi and other Pratylenchus species; Burrowing nematodes, Radopholus similis and other Radopholus species; Reniform nematodes, Rotylenchus robustus, Rotylenchus reniformis and other Rotylenchus species; Scutellonema species; Stubby root nematodes, Trichodorus primitivus and other Trichodorus species, Paratrichodorus species; Stunt nematodes, Tylenchorhynchus claytoni, Tylenchorhynchus dubius and other Tylenchorhynchus species; Citrus nematodes, Tylenchulus species; Dagger nematodes, Xiphinema species; and other plant parasitic nematode species, such as Subanguina spp., Hypsoperine spp., Macroposthonia spp., Melinius spp., Punctodera spp., and Quinisulcius spp..

The compounds of the invention may also have activity against the molluscs. Examples of which include, for example, Ampullariidae; Arion (A. ater, A. circumscriptus, A. hortensis, A. rufus);

Bradybaenidae (Bradybaena fruticum); Cepaea (C. hortensis, C. Nemoralis); ochlodina; Deroceras (D. agrestis, D. empiricorum, D. laeve, D. reticulatum); Discus (D. rotundatus); Euomphalia; Galba (G. trunculata); Helicelia (H. itala, H. obvia); Helicidae Helicigona arbustorum); Helicodiscus; Helix (H. aperta); Limax (L. cinereoniger, L. flavus, L. marginatus, L. maximus, L. tenellus); Lymnaea; Milax (M. gagates, M. marginatus, M. sowerbyi); Opeas; Pomacea (P. canaticulata); Vallonia and Zanitoides.

The term "crops" is to be understood as including also crop plants which have been so transformed by the use of recombinant DNA techniques that they are capable of synthesising one or more selectively acting toxins, such as are known, for example, from toxin-producing bacteria, especially those of the genus Bacillus.

Toxins that can be expressed by such transgenic plants include, for example, insecticidal proteins, for example insecticidal proteins from Bacillus cereus or Bacillus popilliae; or insecticidal proteins from Bacillus thuringiensis, such as δ-endotoxins, e.g. CrylAb, CrylAc, Cryl F, Cry1 Fa2, Cry2Ab, Cry3A, Cry3Bb1 or Cry9C, or vegetative insecticidal proteins (Vip), e.g. Vip1 , Vip2, Vip3 or Vip3A; or insecticidal proteins of bacteria colonising nematodes, for example Photorhabdus spp. or

Xenorhabdus spp., such as Photorhabdus luminescens, Xenorhabdus nematophilus; toxins produced by animals, such as scorpion toxins, arachnid toxins, wasp toxins and other insect-specific neurotoxins; toxins produced by fungi, such as Streptomycetes toxins, plant lectins, such as pea lectins, barley lectins or snowdrop lectins; agglutinins; proteinase inhibitors, such as trypsin inhibitors, serine protease inhibitors, patatin, cystatin, papain inhibitors; ribosome-inactivating proteins (RIP), such as ricin, maize-RIP, abrin, luffin, saporin or bryodin; steroid metabolism enzymes, such as 3-hydroxysteroidoxidase, ecdysteroid-UDP-glycosyl-transferase, cholesterol oxidases, ecdysone inhibitors, HMG-COA-reductase, ion channel blockers, such as blockers of sodium or calcium channels, juvenile hormone esterase, diuretic hormone receptors, stilbene synthase, bibenzyl synthase, chitinases and glucanases.

In the context of the present invention there are to be understood by δ-endotoxins, for example CrylAb, CrylAc, Cryl F, Cry1 Fa2, Cry2Ab, Cry3A, Cry3Bb1 or Cry9C, or vegetative insecticidal proteins (Vip), for example Vip1 , Vip2, Vip3 or Vip3A, expressly also hybrid toxins, truncated toxins and modified toxins. Hybrid toxins are produced recombinantly by a new combination of different domains of those proteins (see, for example, WO 02/15701 ). Truncated toxins, for example a truncated Cry1 Ab, are known. In the case of modified toxins, one or more amino acids of the naturally occurring toxin are replaced. In such amino acid replacements, preferably non-naturally present protease recognition sequences are inserted into the toxin, such as, for example, in the case of Cry3A055, a cathepsin-G-recognition sequence is inserted into a Cry3A toxin (see WO 03/018810). Examples of such toxins or transgenic plants capable of synthesising such toxins are disclosed, for example, in EP-A-0 374 753, WO 93/07278, WO 95/34656, EP-A-0 427 529, EP-A-451 878 and WO 03/052073.

The processes for the preparation of such transgenic plants are generally known to the person skilled in the art and are described, for example, in the publications mentioned above. Cryl-type

deoxyribonucleic acids and their preparation are known, for example, from WO 95/34656, EP-A-0 367 474, EP-A-0 401 979 and WO 90/13651.

The toxin contained in the transgenic plants imparts to the plants tolerance to harmful insects. Such insects can occur in any taxonomic group of insects, but are especially commonly found in the beetles (Coleoptera), two-winged insects (Diptera) and moths (Lepidoptera).

Transgenic plants containing one or more genes that code for an insecticidal resistance and express one or more toxins are known and some of them are commercially available. Examples of such plants are: YieldGard® (maize variety that expresses a CrylAb toxin); YieldGard Rootworm® (maize variety that expresses a Cry3Bb1 toxin); YieldGard Plus® (maize variety that expresses a CrylAb and a Cry3Bb1 toxin); Starlink® (maize variety that expresses a Cry9C toxin); Herculex I® (maize variety that expresses a Cry1 Fa2 toxin and the enzyme phosphinothricine N-acetyltransferase (PAT) to achieve tolerance to the herbicide glufosinate ammonium); NuCOTN 33B® (cotton variety that expresses a Cry1 Ac toxin); Bollgard I® (cotton variety that expresses a Cry 1 Ac toxin); Bollgard II® (cotton variety that expresses a Cry1 Ac and a Cry2Ab toxin); VipCot® (cotton variety that expresses a Vip3A and a CrylAb toxin); NewLeaf® (potato variety that expresses a Cry3A toxin); NatureGard®, Agrisure® GT Advantage (GA21 glyphosate-tolerant trait), Agrisure® CB Advantage (Bt1 1 corn borer (CB) trait) and Protecta®.

Further examples of such transgenic crops are:

1. Bt11 Maize from Syngenta Seeds SAS, Chemin de I'Hobit 27, F-31 790 St. Sauveur, France, registration number C/FR/96/05/10. Genetically modified Zea mays which has been rendered resistant to attack by the European corn borer (Ostrinia nubilalis and Sesamia nonagrioides) by transgenic expression of a truncated CrylAb toxin. Bt1 1 maize also transgenically expresses the enzyme PAT to achieve tolerance to the herbicide glufosinate ammonium.

2. Bt176 Maize from Syngenta Seeds SAS, Chemin de I'Hobit 27, F-31 790 St. Sauveur, France, registration number C/FR/96/05/10. Genetically modified Zea mays which has been rendered resistant to attack by the European corn borer (Ostrinia nubilalis and Sesamia nonagrioides) by transgenic expression of a CrylAb toxin. Bt176 maize also transgenically expresses the enzyme PAT to achieve tolerance to the herbicide glufosinate ammonium.

3. MIR604 Maize from Syngenta Seeds SAS, Chemin de I'Hobit 27, F-31 790 St. Sauveur, France, registration number C/FR/96/05/10. Maize which has been rendered insect-resistant by transgenic expression of a modified Cry3A toxin. This toxin is Cry3A055 modified by insertion of a cathepsin-G- protease recognition sequence. The preparation of such transgenic maize plants is described in WO 03/018810.

4. MON 863 Maize from Monsanto Europe S.A. 270-272 Avenue de Tervuren, B-1 150 Brussels, Belgium, registration number C/DE/02/9. MON 863 expresses a Cry3Bb1 toxin and has resistance to certain Coleoptera insects.

5. IPC 531 Cotton from Monsanto Europe S.A. 270-272 Avenue de Tervuren, B-1 150 Brussels, Belgium, registration number C/ES/96/02.

6. 1507 Maize from Pioneer Overseas Corporation, Avenue Tedesco, 7 B-1 160 Brussels, Belgium, registration number C/NL/00/10. Genetically modified maize for the expression of the protein Cry1 F for achieving resistance to certain Lepidoptera insects and of the PAT protein for achieving tolerance to the herbicide glufosinate ammonium.

7. NK603 * MON 810 Maize from Monsanto Europe S.A. 270-272 Avenue de Tervuren, B-1 150 Brussels, Belgium, registration number C/GB/02/M3/03. Consists of conventionally bred hybrid maize varieties by crossing the genetically modified varieties NK603 and MON 810. NK603 * MON 810 Maize transgenically expresses the protein CP4 EPSPS, obtained from Agrobacterium sp. strain CP4, which imparts tolerance to the herbicide Roundup® (contains glyphosate), and also a CrylAb toxin obtained from Bacillus thuringiensis subsp. kurstaki which brings about tolerance to certain

Lepidoptera, include the European corn borer.

Transgenic crops of insect-resistant plants are also described in BATS (Zentrum fur Biosicherheit und Nachhaltigkeit, Zentrum BATS, Clarastrasse 13, 4058 Basel, Switzerland) Report 2003,

(http://bats.ch).

The term "crops" is to be understood as including also crop plants which have been so transformed by the use of recombinant DNA techniques that they are capable of synthesising antipathogenic substances having a selective action, such as, for example, the so-called "pathogenesis-related proteins" (PRPs, see e.g. EP-A-0 392 225). Examples of such antipathogenic substances and transgenic plants capable of synthesising such antipathogenic substances are known, for example, from EP-A-0 392 225, WO 95/33818 and EP-A-0 353 191. The methods of producing such transgenic plants are generally known to the person skilled in the art and are described, for example, in the publications mentioned above.

Antipathogenic substances which can be expressed by such transgenic plants include, for example, ion channel blockers, such as blockers for sodium and calcium channels, for example the viral KP1 , KP4 or KP6 toxins; stilbene synthases; bibenzyl synthases; chitinases; glucanases; the so-called "pathogenesis-related proteins" (PRPs; see e.g. EP-A-0 392 225); antipathogenic substances produced by microorganisms, for example peptide antibiotics or heterocyclic antibiotics (see e.g. WO 95/33818) or protein or polypeptide factors involved in plant pathogen defence (so-called "plant disease resistance genes", as described in WO 03/000906).

Further areas of use of the compositions according to the invention are the protection of stored goods and store rooms and the protection of raw materials, such as wood, textiles, floor coverings or buildings, and also in the hygiene sector, especially the protection of humans, domestic animals and productive livestock against pests of the mentioned type.

The present invention also provides a method for controlling pests (such as mosquitoes and other disease vectors; see also http://www.who.int/malaria/vector_control/irs/en/). In one embodiment, the method for controlling pests comprises applying the compositions of the invention to the target pests, to their locus or to a surface or substrate by brushing, rolling, spraying, spreading or dipping. By way of example, an IRS (indoor residual spraying) application of a surface such as a wall, ceiling or floor surface is contemplated by the method of the invention. In another embodiment, it is contemplated to apply such compositions to a substrate such as non-woven or a fabric material in the form of (or which can be used in the manufacture of) netting, clothing, bedding, curtains and tents.

In one embodiment, the method for controlling such pests comprises applying a pesticidally effective amount of the compositions of the invention to the target pests, to their locus, or to a surface or substrate so as to provide effective residual pesticidal activity on the surface or substrate. Such application may be made by brushing, rolling, spraying, spreading or dipping the pesticidal composition of the invention. By way of example, an IRS application of a surface such as a wall, ceiling or floor surface is contemplated by the method of the invention so as to provide effective residual pesticidal activity on the surface. In another embodiment, it is contemplated to apply such compositions for residual control of pests on a substrate such as a fabric material in the form of (or which can be used in the manufacture of) netting, clothing, bedding, curtains and tents.

Substrates including non-woven, fabrics or netting to be treated may be made of natural fibres such as cotton, raffia, jute, flax, sisal, hessian, or wool, or synthetic fibres such as polyamide, polyester, polypropylene, polyacrylonitrile or the like. The polyesters are particularly suitable. The methods of textile treatment are known, e.g. WO 2008/151984, WO 2003/034823, US 5631072, WO 2005/64072, WO2006/128870, EP 1724392, WO20051 13886 or WO 2007/090739.

Further areas of use of the compositions according to the invention are the field of tree injection/trunk treatment for all ornamental trees as well all sort of fruit and nut trees.

In the field of tree injection/trunk treatment, the compounds according to the present invention are especially suitable against wood-boring insects from the order Lepidoptera as mentioned above and from the order Coleoptera, especially against woodborers listed in the following tables A and B:

Table A. Examples of exotic woodborers of economic importance. Family Species Host or Crop Infested

Buprestidae Agrilus planipennis Ash

Cerambycidae Anoplura glabripennis Hardwoods

Xylosandrus crassiusculus Hardwoods

Scolytidae X. mutilatus Hardwoods

Tomicus piniperda Conifers

Table B. Examples of native woodborers of economic importance.

Family Species Host or Crop Infested

Agrilus anxius Birch

Agrilus politus Willow, Maple

Agrilus sayi Bayberry, Sweetfern

Agrilus vittaticolllis Apple, Pear, Cranberry,

Serviceberry, Hawthorn

Chrysobothris femorata Apple, Apricot, Beech, Boxelder,

Buprestidae Cherry, Chestnut, Currant, Elm,

Hawthorn, Hackberry, Hickory, Horsechestnut, Linden, Maple, Mountain-ash, Oak, Pecan, Pear, Peach, Persimmon, Plum, Poplar, Quince, Redbud, Serviceberry, Sycamore, Walnut, Willow

Texania campestris Basswood, Beech, Maple, Oak,

Sycamore, Willow, Yellow-poplar

Goes pulverulentus Beech, Elm, Nuttall, Willow, Black oak, Cherrybark oak, Water oak,

Cerambycidae Sycamore

Goes tigrinus Oak Family Species Host or Crop Infested

Neoclytus acuminatus Ash, Hickory, Oak, Walnut, Birch,

Beech, Maple, Eastern

hophornbeam, Dogwood,

Persimmon, Redbud, Holly, Hackberry, Black locust,

Honeylocust, Yellow-poplar, Chestnut, Osage-orange, Sassafras, Lilac, Mountain-mahogany, Pear, Cherry, Plum, Peach, Apple, Elm, Basswood, Sweetgum

Neoptychodes trilineatus Fig, Alder, Mulberry, Willow, Netleaf hackberry

Oberea ocellata Sumac, Apple, Peach, Plum, Pear,

Currant, Blackberry

Oberea tripunctata Dogwood, Viburnum, Elm,

Sourwood, Blueberry,

Rhododendron, Azalea, Laurel, Poplar, Willow, Mulberry

Oncideres cingulata Hickory, Pecan, Persimmon, Elm,

Sourwood, Basswood, Honeylocust, Dogwood, Eucalyptus, Oak, Hackberry, Maple, Fruit trees

Saperda calcarata Poplar

Strophiona nitens Chestnut, Oak, Hickory, Walnut,

Beech, Maple

Corthylus columbianus Maple, Oak, Yellow-poplar, Beech,

Boxelder, Sycamore, Birch,

Basswood, Chestnut, Elm

Scolytidae

Dendroctonus frontalis Pine

Dryocoetes betulae Birch, Sweetgum, Wild cherry,

Beech, Pear Family Species Host or Crop Infested

Monarthrum fasciatum Oak, Maple, Birch, Chestnut,

Sweetgum, Blackgum, Poplar,

Hickory, Mimosa, Apple, Peach, Pine

Phloeotribus liminaris Peach, Cherry, Plum, Black cherry,

Elm, Mulberry, Mountain-ash

Pseudopityophthorus pruinosus Oak, American beech, Black cherry,

Chickasaw plum, Chestnut, Maple,

Hickory, Hornbeam, Hophornbeam

Paranthrene simulans Oak, American chestnut

Sannina uroceriformis Persimmon

Synanthedon exitiosa Peach, Plum, Nectarine, Cherry,

Apricot, Almond, Black cherry

Synanthedon pictipes Peach, Plum, Cherry, Beach, Black

Cherry

Sesiidae

Synanthedon rubrofascia Tupelo

Synanthedon scitula Dogwood, Pecan, Hickory, Oak,

Chestnut, Beech, Birch, Black cherry,

Elm, Mountain-ash, Viburnum,

Willow, Apple, Loquat, Ninebark,

Bayberry

Vitacea polistiformis Grape

The present invention may be also used to control any insect pests that may be present in turfgrass, including for example beetles, caterpillars, fire ants, ground pearls, millipedes, sow bugs, mites, mole crickets, scales, mealybugs ticks, spittlebugs, southern chinch bugs and white grubs. The present invention may be used to control insect pests at various stages of their life cycle, including eggs, larvae, nymphs and adults.

In particular, the present invention may be used to control insect pests that feed on the roots of turfgrass including white grubs (such as Cyclocephala spp. (e.g. masked chafer, C. lurida),

Rhizotrogus spp. (e.g. European chafer, R. majalis), Cotinus spp. (e.g. Green June beetle, C. nitida), Popillia spp. (e.g. Japanese beetle, P. japonica), Phyllophaga spp. (e.g. May/June beetle), Ataenius spp. (e.g. Black turfgrass ataenius, A. spretulus), Maladera spp. (e.g. Asiatic garden beetle, M. castanea) and Tomarus spp.), ground pearls (Margarodes spp.), mole crickets (tawny, southern, and short-winged; Scapteriscus spp., Gryllotalpa africana) and leatherjackets (European crane fly, Tipula spp.).

The present invention may also be used to control insect pests of turfgrass that are thatch dwelling, including armyworms (such as fall armyworm Spodoptera frugiperda, and common armyworm

Pseudaletia unipuncta), cutworms, billbugs (Sphenophorus spp. , such as S. venatus verstitus and S. parvulus), and sod webworms (such as Crambus spp. and the tropical sod webworm, Herpetogramma phaeopteralis).

The present invention may also be used to control insect pests of turfgrass that live above the ground and feed on the turfgrass leaves, including chinch bugs (such as southern chinch bugs, Blissus insularis), Bermudagrass mite (Eriophyes cynodoniensis), rhodesgrass mealybug (Antonina graminis), two-lined spittlebug (Propsapia bicincta), leafhoppers, cutworms (Noctuidae family), and greenbugs. The present invention may also be used to control other pests of turfgrass such as red imported fire ants (Solenopsis invicta) that create ant mounds in turf.

In the hygiene sector, the compositions according to the invention are active against ectoparasites such as hard ticks, soft ticks, mange mites, harvest mites, flies (biting and licking), parasitic fly larvae, lice, hair lice, bird lice and fleas.

Examples of such parasites are:

Of the order Anoplurida: Haematopinus spp., Linognathus spp., Pediculus spp. and Phtirus spp., Solenopotes spp..

Of the order Mallophagida: Trimenopon spp., Menopon spp., Trinoton spp., Bovicola spp.,

Werneckiella spp., Lepikentron spp., Damalina spp., Trichodectes spp. and Felicola spp..

Of the order Diptera and the suborders Nematocerina and Brachycerina, for example Aedes spp., Anopheles spp., Culex spp., Simulium spp., Eusimulium spp., Phlebotomus spp., Lutzomyia spp., Culicoides spp., Chrysops spp., Hybomitra spp., Atylotus spp., Tabanus spp., Haematopota spp., Philipomyia spp., Braula spp., Musca spp., Hydrotaea spp., Stomoxys spp., Haematobia spp., Morellia spp., Fannia spp., Glossina spp., Calliphora spp., Lucilia spp., Chrysomyia spp., Wohlfahrtia spp., Sarcophaga spp., Oestrus spp., Hypoderma spp., Gasterophilus spp., Hippobosca spp., Lipoptena spp. and Melophagus spp..

Of the order Siphonapterida, for example Pulex spp., Ctenocephalides spp., Xenopsylla spp., Ceratophyllus spp..

Of the order Heteropterida, for example Cimex spp., Triatoma spp., Rhodnius spp., Panstrongylus spp.. Of the order Blattarida, for example Blatta orientalis, Periplaneta americana, Blattelagermanica and Supella spp.. Of the subclass Acaria (Acarida) and the orders Meta- and Meso-stigmata, for example Argas spp., Ornithodorus spp., Otobius spp., Ixodes spp., Amblyomma spp., Boophilus spp., Dermacentor spp., Haemophysalis spp., Hyalomma spp., Rhipicephalus spp., Dermanyssus spp., Raillietia spp., Pneumonyssus spp., Sternostoma spp. and Varroa spp.. Of the orders Actinedida (Prostigmata) and Acaridida (Astigmata), for example Acarapis spp.,

Cheyletiella spp., Ornithocheyletia spp., Myobia spp., Psorergatesspp., Demodex spp., Trombicula spp., Listrophorus spp., Acarus spp., Tyrophagus spp., Caloglyphus spp., Hypodectes spp.,

Pterolichus spp., Psoroptes spp., Chorioptes spp., Otodectes spp., Sarcoptes spp., Notoedres spp., Knemidocoptes spp., Cytodites spp. and Laminosioptes spp..

The compositions according to the invention are also suitable for protecting against insect infestation in the case of materials such as wood, textiles, plastics, adhesives, glues, paints, paper and card, leather, floor coverings and buildings.

The compositions according to the invention can be used, for example, against the following pests: beetles such as Hylotrupes bajulus, Chlorophorus pilosis, Anobium punctatum, Xestobium

rufovillosum, Ptilinuspecticornis, Dendrobium pertinex, Ernobius mollis, Priobium carpini, Lyctus brunneus, Lyctus africanus, Lyctus planicollis, Lyctus linearis, Lyctus pubescens, Trogoxylon aequale, Minthesrugicollis, Xyleborus spec.,Tryptodendron spec, Apate monachus, Bostrychus capucins, Heterobostrychus brunneus, Sinoxylon spec, and Dinoderus minutus, and also hymenopterans such as Sirex juvencus, Urocerus gigas, Urocerus gigas taignus and Urocerus augur, and termites such as Kalotermes flavicollis, Cryptotermes brevis, Heterotermes indicola, Reticulitermes flavipes,

Reticulitermes santonensis, Reticulitermes lucifugus, Mastotermes darwiniensis, Zootermopsis nevadensis and Coptotermes formosanus, and bristletails such as Lepisma saccharina. The compounds according to the invention can be used as pesticidal agents in unmodified form, but they are generally formulated into compositions in various ways using formulation adjuvants, such as carriers, solvents and surface-active substances. The formulations can be in various physical forms, e.g. in the form of dusting powders, gels, wettable powders, water-dispersible granules, water- dispersible tablets, effervescent pellets, emulsifiable concentrates, microemulsifiable concentrates, oil- in-water emulsions, oil-flowables, aqueous dispersions, oily dispersions, suspo-emulsions, capsule suspensions, emulsifiable granules, soluble liquids, water-soluble concentrates (with water or a water- miscible organic solvent as carrier), impregnated polymer films or in other forms known e.g. from the Manual on Development and Use of FAO and WHO Specifications for Pesticides, United Nations, First Edition, Second Revision (2010). Such formulations can either be used directly or diluted prior to use. The dilutions can be made, for example, with water, liquid fertilisers, micronutrients, biological organisms, oil or solvents.

The formulations can be prepared e.g. by mixing the active ingredient with the formulation adjuvants in order to obtain compositions in the form of finely divided solids, granules, solutions, dispersions or emulsions. The active ingredients can also be formulated with other adjuvants, such as finely divided solids, mineral oils, oils of vegetable or animal origin, modified oils of vegetable or animal origin, organic solvents, water, surface-active substances or combinations thereof.

The active ingredients can also be contained in very fine microcapsules. Microcapsules contain the active ingredients in a porous carrier. This enables the active ingredients to be released into the environment in controlled amounts (e.g. slow-release). Microcapsules usually have a diameter of from 0.1 to 500 microns. They contain active ingredients in an amount of about from 25 to 95 % by weight of the capsule weight. The active ingredients can be in the form of a monolithic solid, in the form of fine particles in solid or liquid dispersion or in the form of a suitable solution. The encapsulating membranes can comprise, for example, natural or synthetic rubbers, cellulose, styrene/butadiene copolymers, polyacrylonitrile, polyacrylate, polyesters, polyamides, polyureas, polyurethane or chemically modified polymers and starch xanthates or other polymers that are known to the person skilled in the art. Alternatively, very fine microcapsules can be formed in which the active ingredient is contained in the form of finely divided particles in a solid matrix of base substance, but the microcapsules are not themselves encapsulated. The formulation adjuvants that are suitable for the preparation of the compositions according to the invention are known per se. As liquid carriers there may be used: water, toluene, xylene, petroleum ether, vegetable oils, acetone, methyl ethyl ketone, cyclohexanone, acid anhydrides, acetonitrile, acetophenone, amyl acetate, 2-butanone, butylene carbonate, chlorobenzene, cyclohexane, cyclohexanol, alkyl esters of acetic acid, diacetone alcohol, 1 ,2-dichloropropane, diethanolamine, p- diethylbenzene, diethylene glycol, diethylene glycol abietate, diethylene glycol butyl ether, diethylene glycol ethyl ether, diethylene glycol methyl ether, A/,A/-dimethylformamide, dimethyl sulfoxide, 1 ,4- dioxane, dipropylene glycol, dipropylene glycol methyl ether, dipropylene glycol dibenzoate, diproxitol, alkylpyrrolidone, ethyl acetate, 2-ethylhexanol, ethylene carbonate, 1 ,1 , 1-trichloroethane, 2- heptanone, alpha-pinene, d-limonene, ethyl lactate, ethylene glycol, ethylene glycol butyl ether, ethylene glycol methyl ether, gamma-butyrolactone, glycerol, glycerol acetate, glycerol diacetate, glycerol triacetate, hexadecane, hexylene glycol, isoamyl acetate, isobornyl acetate, isooctane, isophorone, isopropylbenzene, isopropyl myristate, lactic acid, laurylamine, mesityl oxide, methoxy- propanol, methyl isoamyl ketone, methyl isobutyl ketone, methyl laurate, methyl octanoate, methyl oleate, methylene chloride, m-xylene, n-hexane, n-octylamine, octadecanoic acid, octylamine acetate, oleic acid, oleylamine, o-xylene, phenol, polyethylene glycol, propionic acid, propyl lactate, propylene carbonate, propylene glycol, propylene glycol methyl ether, p-xylene, toluene, triethyl phosphate, triethylene glycol, xylenesulfonic acid, paraffin, mineral oil, trichloroethylene, perchloroethylene, ethyl acetate, amyl acetate, butyl acetate, propylene glycol methyl ether, diethylene glycol methyl ether, methanol, ethanol, isopropanol, and alcohols of higher molecular weight, such as amyl alcohol, tetrahydrofurfuryl alcohol, hexanol, octanol, ethylene glycol, propylene glycol, glycerol, A/-methyl-2- pyrrolidone and the like. Suitable solid carriers are, for example, talc, titanium dioxide, pyrophyllite clay, silica, attapulgite clay, kieselguhr, limestone, calcium carbonate, bentonite, calcium montmorillonite, cottonseed husks, wheat flour, soybean flour, pumice, wood flour, ground walnut shells, lignin and similar substances.

A large number of surface-active substances can advantageously be used in both solid and liquid formulations, especially in those formulations which can be diluted with a carrier prior to use. Surface- active substances may be anionic, cationic, non-ionic or polymeric and they can be used as emulsifiers, wetting agents or suspending agents or for other purposes. Typical surface-active substances include, for example, salts of alkyl sulfates, such as diethanolammonium lauryl sulfate; salts of alkylarylsulfonates, such as calcium dodecylbenzenesulfonate; alkylphenol/alkylene oxide addition products, such as nonylphenol ethoxylate; alcohol/alkylene oxide addition products, such as tridecylalcohol ethoxylate; soaps, such as sodium stearate; salts of alkylnaphthalenesulfonat.es, such as sodium dibutylnaphthalenesulfonate; dialkyl esters of sulfosuccinate salts, such as sodium di(2- ethylhexyl)sulfosuccinate; sorbitol esters, such as sorbitol oleate; quaternary amines, such as lauryltrimethylammonium chloride, polyethylene glycol esters of fatty acids, such as polyethylene glycol stearate; block copolymers of ethylene oxide and propylene oxide; and salts of mono- and di- alkylphosphate esters; and also further substances described e.g. in McCutcheon's Detergents and Emulsifiers Annual, MC Publishing Corp., Ridgewood New Jersey (1981 ).

Further adjuvants that can be used in pesticidal formulations include crystallisation inhibitors, viscosity modifiers, suspending agents, dyes, anti-oxidants, foaming agents, light absorbers, mixing auxiliaries, antifoams, complexing agents, neutralising or pH-modifying substances and buffers, corrosion inhibitors, fragrances, wetting agents, take-up enhancers, micronutrients, plasticisers, glidants, lubricants, dispersants, thickeners, antifreezes, microbicides, and liquid and solid fertilisers.

The compositions according to the invention can include an additive comprising an oil of vegetable or animal origin, a mineral oil, alkyl esters of such oils or mixtures of such oils and oil derivatives. The amount of oil additive in the composition according to the invention is generally from 0.01 to 10 %, based on the mixture to be applied. For example, the oil additive can be added to a spray tank in the desired concentration after a spray mixture has been prepared. Preferred oil additives comprise mineral oils or an oil of vegetable origin, for example rapeseed oil, olive oil or sunflower oil, emulsified vegetable oil, alkyl esters of oils of vegetable origin, for example the methyl derivatives, or an oil of animal origin, such as fish oil or beef tallow. Preferred oil additives comprise alkyl esters of C8-C22 fatty acids, especially the methyl derivatives of C12-C18 fatty acids, for example the methyl esters of lauric acid, palmitic acid and oleic acid (methyl laurate, methyl palmitate and methyl oleate, respectively). Many oil derivatives are known from the Compendium of Herbicide Adjuvants, 10^th Edition, Southern Illinois University, 2010.

The inventive compositions generally comprise from 0.1 to 99 % by weight, especially from 0.1 to 95 % by weight, of compounds of the present invention and from 1 to 99.9 % by weight of a formula- tion adjuvant which preferably includes from 0 to 25 % by weight of a surface-active substance. Whereas commercial products may preferably be formulated as concentrates, the end user will normally employ dilute formulations.

The rates of application vary within wide limits and depend on the nature of the soil, the method of application, the crop plant, the pest to be controlled, the prevailing climatic conditions, and other factors governed by the method of application, the time of application and the target crop. As a general guideline compounds may be applied at a rate of from 1 to 2000 l/ha, especially from 10 to 1000 l/ha.

Preferred formulations can have the following compositions (weight %):

Emulsifiable concentrates:

active ingredient: 1 to 95 %, preferably 60 to 90 %

surface-active agent: 1 to 30 %, preferably 5 to 20 %

liquid carrier: 1 to 80 %, preferably 1 to 35 %

Dusts:

active ingredient: 0.1 to 10 %, preferably 0.1 to 5 %

solid carrier: 99.9 to 90 %, preferably 99.9 to 99 %

Suspension concentrates:

active ingredient: 5 to 75 %, preferably 10 to 50 %

water: 94 to 24 %, preferably 88 to 30 %

surface-active agent: 1 to 40 %, preferably 2 to 30 %

Wettable powders:

active ingredient: 0.5 to 90 %, preferably 1 to 80 %

surface-active agent: 0.5 to 20 %, preferably 1 to 15 %

solid carrier: 5 to 95 %, preferably 15 to 90 %

Granules:

active ingredient: 0.1 to 30 %, preferably 0.1 to 15 %

solid carrier: 99.5 to 70 %, preferably 97 to 85 %

The following Examples further illustrate, but do not limit, the invention. Wettable powders a) b) c) active ingredients 25 % 50 % 75 % sodium lignosulfonate 5 % 5 % sodium lauryl sulfate 3 % 5 % sodium diisobutylnaphthalenesulfonate 6 % 10 % phenol polyethylene glycol ether (7-8 mol of ethylene 2 %

oxide) highly dispersed silicic acid 5 % 10 % 10 %

Kaolin 62 % 27 %

The combination is thoroughly mixed with the adjuvants and the mixture is thoroughly ground in a suitable mill, affording wettable powders that can be diluted with water to give suspensions of the desired concentration.

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

Emulsifiable concentrate active ingredients 10 % octylphenol polyethylene glycol ether (4-5 mol of ethylene 3 %

oxide) calcium dodecylbenzenesulfonate 3 % castor oil polyglycol ether (35 mol of ethylene oxide) 4 %

Cyclohexanone 30 % xylene mixture 50 %

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

Ready-for-use dusts are obtained by mixing the combination with the carrier and grinding the mixture in a suitable mill. Such powders can also be used for dry dressings for seed.

The combination is mixed and ground with the adjuvants, and the mixture is moistened with water. The mixture is extruded and then dried in a stream of air.

The finely ground combination is uniformly applied, in a mixer, to the kaolin moistened with polyethylene glycol. Non-dusty coated granules are obtained in this manner.

Suspension concentrate active ingredients 40 % propylene glycol 10 % nonylphenol polyethylene glycol ether (15 mol of ethylene oxide) 6 %

Sodium lignosulfonate 10 % carboxymethylcellulose 1 % silicone oil (in the form of a 75 % emulsion in water) 1 %

Water 32 %

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

Flowable concentrate for seed treatment

Slow Release Capsule Suspension

28 parts of the combination are mixed with 2 parts of an aromatic solvent and 7 parts of toluene diisocyanate/polymethylene-polyphenylisocyanate-mixture (8: 1 ). This mixture is emulsified in a mixture of 1 .2 parts of polyvinylalcohol, 0.05 parts of a defoamer and 51 .6 parts of water until the desired particle size is achieved. To this emulsion a mixture of 2.8 parts 1 ,6-diaminohexane in 5.3 parts of water is added. The mixture is agitated until the polymerization reaction is completed. The obtained capsule suspension is stabilized by adding 0.25 parts of a thickener and 3 parts of a dispersing agent. The capsule suspension formulation contains 28% of the active ingredients. The medium capsule diameter is 8-15 microns. The resulting formulation is applied to seeds as an aqueous suspension in an apparatus suitable for that purpose.

Formulation types include an emulsion concentrate (EC), a suspension concentrate (SC), a suspo- emulsion (SE), a capsule suspension (CS), a water dispersible granule (WG), an emulsifiable granule (EG), an emulsion, water in oil (EO), an emulsion, oil in water (EW), a micro-emulsion (ME), an oil dispersion (OD), an oil miscible flowable (OF), an oil miscible liquid (OL), a soluble concentrate (SL), an ultra-low volume suspension (SU), an ultra-low volume liquid (UL), a technical concentrate (TK), a dispersible concentrate (DC), a wettable powder (WP), a soluble granule (SG) or any technically feasible formulation in combination with agriculturally acceptable adjuvants.

Preparatory Examples:

"Mp" means melting point in °C. Free radicals represent methyl groups. H NMR measurements were recorded on a Brucker 400MHz spectrometer, chemical shifts are given in ppm relevant to a TMS standard. Spectra measured in deuterated solvents as indicated. Common abbreviations: aq = aqueous, min = minute, h = hour, sat = saturated, Rt = retention time, mCPBA = meta- chloroperoxybenzoic acid, MeOH = methanol, EtOH = ethanol, NaHCCh = sodium hydrogen carbonate, Na2C03 = sodium carbonate, HCI = hydrogen chloride, CH2CI2 = dichloromethane, Et3N = triethylamine, DMF = Ν,Ν-dimethylformamide, NBS = N-bromosuccinimide, PdCl2(dppf) = [1 , 1-bis (diphenylphosphino)ferrocene]dichloropalladium(ll). Either one of the LCMS methods below was used to characterize the compounds. The characteristic LCMS values obtained for each compound were the retention time ("Rt", recorded in min) and the measured molecular ion (M+H)⁺.

LCMS Methods:

Method 1 :

SC_BASE, Apparatus: Agilent 1 100 Bin. Pump: G1312A, degasser; autosampler, ColCom, DAD: Agilent G1315B, 220-320 nm, MSD: Agilent LC/MSD G6130B ESI, pos/neg 100-800; ELSD PL- ELS2100 gas flow 1.1 ml/min, gas temp: 50°C ; column: Waters XSelect™ C18, 30x2.1 mm, 3.5μ, Temp: 25 °C, Flow: 1 mL/min, Gradient: to = 2% A, ti.emin = 98% A, t₃min = 98% A, Posttime: 1 .3 min, Eluent A: 95% acetonitrile + 5% 10mM ammonium bicarbonate in water in acetonitrile, Eluent B: 10mM ammonium bicarbonate in water (pH=9.5).

Method 2: AN_BASE, Apparatus: Agilent 1 100 Bin. Pump: G1312A, degasser; autosampler, ColCom, DAD: Agilent G1315B, 220-320 nm, MSD: Agilent LC/MSD G6130B ESI, pos/neg 100-800; ELSD PL- ELS2100 gas flow 1.1 ml/min, gas temp: 50°C; column: Waters XSelect™ C18, 50x2.1 mm, 3.5μ, Temp: 25 °C, Flow: 0.8 mL/min, Gradient: to = 2% A, t₃.5min = 98% A, temin = 98% A, Posttime: 2 min, Eluent A: 95% acetonitrile + 5% 10mM ammonium bicarbonate in water in acetonitrile, Eluent B: 10mM ammonium bicarbonate in water (pH=9.5).

Method 3:

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 μηη, 30 x 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.

Method 4:

Spectra were recorded on a Mass Spectrometer from Waters (SQD, SQDII 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 mm, 30 x 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: 10-100% B in 1.2 min; Flow (ml/min) 0.85.

Method 5:

Spectra were recorded on an ACQUITY SQD Mass Spectrometer from Waters (Single quadrupole mass spectrometer), lonisation method: Electrospray. Polarity: positive ions. Capillary (kV) 3.00, Cone (V) 20.00, Extractor (V) 3.00, Source Temperature (°C) 150, Desolvation Temperature (°C) 400, Cone Gas Flow (L/Hr) 60, Desolvation Gas Flow (L/Hr) 700; Mass range: 100 to 800 Da; DAD Wavelength range (nm): 210 to 400.

Method Waters ACQUITY UPLC with the following HPLC gradient conditions

(Solvent A: Water/Methanol 9:1 ,0.1 % formic acid and Solvent B: Acetonitrile,0.1 % formic acid)

Time (minutes) A (%) B (%) Flow rate (ml/min)

0 100 0 0.75

2.5 0 100 0.75 2.8 0 100 0.75

3.0 100 0 0.75

Type of column: Waters ACQUITY UPLC HSS T3; Column length: 30 mm; Internal diameter of column: 2.1 mm; Particle Size: 1 .8 micron; Temperature: 60°C.

EXAMPLE P1 : Preparation of 3-ethylsulfonyl-2-[1-methyl-5-[3-(trifluoromethvnpyrrolidin-1-yllimidazol- 2-vH-5-(trifluoromethvDpyridine (compound P9):

Step 1 : Preparation of 3-chloro-2-(1 H-imidazol-2-yl)-5-(trifluoromethyl)pyridine

To a solution of 3-chloro-5-(trifluoromethyl)pyridine-2-carbonitrile (4.0 g, 19.37 mmol) in methanol (25 ml) was added sodium methoxide (30% (w/w) in MeOH) (0.192 g, 1.066 mmol, 0.20 ml, 30%) and the mixture was stirred at ambient temperature for 18 hours. 2,2-Diethoxy-ethanamine (2.75 g, 20.63 mmol, 3.0 ml) and acetic acid (2.36 g, 39.3 mmol, 2.25 ml) were added and the reaction mixture was heated at reflux for 30 min. The reaction mixture was cooled to ambient temperature, 6N HCI (aq) (10 ml) was added and the mixture was heated at reflux for 3 h. The reaction mixture was concentrated. To the residue was added water and the pH of the aqueous mixture was adjusted to ~9 with sat. Na2C03 (aq). The precipitated solid was filtered off, washed twice with water and dried. The crude product was purified over silica by flash column chromatography (0-50% ethyl acetate gradient in heptane) to afford the title compound (2.94 g) as a solid. LCMS (method 1 ): 248 (M+H)⁺, retention time 2.03 min. Ή-NMR (DMSO-d6, ppm) 7.31 (2H), 8.52 (1 H), 8.95 (1 H), 13.09 (1 H).

Step 2: Preparation of 3-chloro-2-(1-methylimidazol-2-yl)-5-(trifluoromethyl)pyridine

To a solution of 3-chloro-2-(1 H-imidazol-2-yl)-5-(trifluoromethyl)pyridine (2.9 g, 1 1.71 mmol) in dry tetrahydrofuran (90 ml) was added sodium hydride (0.703 g, 17.57 mmol, 60 wt%). After stirring for 10 min a yellow suspension was obtained, lodomethane (3.18 g, 22.39 mmol, 1.4 ml) was added and the mixture was stirred at ambient temperature for 18 hours. An almost clear brown solution was obtained. The reaction mixture was poured into water and brine was added (water/brine -1/1 ). The aqueous mixture was extracted twice with ethyl acetate. The combined organic layers were dried over sodium sulfate and concentrated. The crude product was purified over silica by flash column chromatography

(10-50% ethyl acetate gradient in heptane) to afford the title compound (2.75 g) as an oil. LCMS (method 1 ): 262 (M+H)⁺, retention time 1.94 min. Ή-NMR (CDCIs, ppm) 3.85 (3H), 7.06 (1 H), 7.26 (1 H), 8.09 (1 H), 8.82 (1 H). Step 3: Preparation of 3-ethylsulfanyl-2-(1-meth limidazol-2-yl)-5-(trifluoromethyl)pyridine

To a solution of 3-chloro-2-(1-methylimidazol-2-yl)-5-(trifluoromethyl)pyridine (2.75 g, 10.51 mmol) in dry N,N-dimethylformamide (20 ml) was added added sodium ethanethiolate (1.061 g, 12.61 mmol) and the mixture was stirred at ambient temperature for 1 hour. The reaction mixture was poured into water/brine (1/1 ) and the aqueous mixture was extracted with ethyl acetate. The organic layer was washed twice with water/brine (1/1 ), dried over sodium sulfate and concentrated. The residue was purified over silica by flash column chromatography (5-50% ethyl acetate gradient in heptane) to afford the title compound (2.67 g) as a solid, mp 87-88°C. LCMS (method 2): 288 (M+H)⁺, retention time 3.35 min. Ή-NMR (CDCIs, ppm) 1.40 (3H), 2.96 (2H), 3.93 (3H), 7.03 (1 H), 7.26 (1 H), 7.79 (1 H), 8.60 (1 H).

Step 4: Preparation of 3-ethylsulfonyl-2-(1-meth limidazol-2-yl)-5-(trifluoromethyl)pyridine

To a solution of 3-ethylsulfanyl-2-(1-methylimidazol-2-yl)-5-(trifluoromethyl)pyridine (2.67 g, 9.29 mmol) in dichloromethane (80 ml) was added mCPBA (70 wt% in water) (6.29 g, 25.5 mmol, 70%) in one portion. The mixture was stirred at ambient temperature for 4 hours. The reaction mixture was diluted with dichloromethane, washed with sat. aqueous sodium thiosulfate solution/sat. NaHCCh (1/1 ), with sat. NaHCCh, dried over sodium sulfate and concentrated. The residue was purified over silica by flash column chromatography (10-75% ethyl acetate gradient in heptane) to afford the title compound (2.48 g) as a solid, mp 149-150°C. LCMS (method 2): 320 (M+H)⁺, retention time 3.10 min. Ή-NMR (CDCI3, ppm) 1.37 (3H), 3.77 (3H), 4.05 (2H), 7.09 (1 H), 7.18 (1 H), 8.71 (1 H), 9.1 1 (1 H). Step 5: Preparation of 2-(5-bromo-1-meth l-imidazol-2-yl)-3-ethylsulfonyl-5-(trifluoromethyl)pyridine

To a solution of 3-ethylsulfonyl-2-(1-methylimidazol-2-yl)-5-(trifluoromethyl)pyridine (319 mg, 0.999 mmol) in chloroform (10 ml) was added NBS (190 mg, 1.068 mmol) and the mixture was heated at 60°C (oil bath temperature) for 1 hour. The reaction mixture was concentrated and the residue was purified over silica by flash column chromatography (5-40% ethyl acetate gradient in heptane) to afford the title compound (290 mg) as a solid. LCMS (method 1 ): 398/400 (M+H)⁺, retention time 2.17 min. Ή-NMR (CDCI3, ppm) 1.38 (3H), 3.70 (3H), 3.99 (2H), 7.18 (1 H), 8.71 (1 H), 9.20 (1 H). Step 6: Preparation of 3-ethylsulfonyl-2-[1-methyl-5-[3-(trifluoromethyl)pyrrolidin-1-yl]imidazol-2-yl]-5- (trifluoromethyl)pyridine (title com ound P9)

A solution of 3-(trifluoro-methyl)pyrrolidine (41.9 mg, 0.301 mmol) in dry N,N-dimethylformamide (0.2 ml) was added to a suspension of sodium hydride (12.05 mg, 0.301 mmol, 60% in mineral oil) in dry N,N-dimethylformamide (1.5 ml) at 0-5°C. The mixture was stirred at 0-5°C for 10 minutes, then warmed to room temperature for 20 minutes until gas evolution ceased. Above reaction mixture was added dropwise to a solution of 2-(5-bromo-1-methyl-imidazol-2-yl)-3-ethylsulfonyl-5-(trifluoromethyl) pyridine (100.0 mg, 0.251 mmol) in N,N-dimethylformamide (2.0 ml), then the mixture was stirred at room temperature for 30 minutes and at 50°C for 2 hours. 3-Ethylsulfonyl-2-[1-methyl-5-[3-(trifluoro- methyl)pyrrolidin-1-yl]imidazol-2-yl]-5-(trifluoromethyl)pyridine (compound P9) was observed as indicated by LCMS analysis: LCMS (method 4): 457 (M+H)⁺; retention time: 0.97 min. Compound P9 may be isolated in analogy to compound P6 by following the general preparation method (EXAMPLE P6 below). EXAMPLE P2: Preparation of 2-(5-bromo-4-methyl-1 ,2,4-triazol-3-yl)-3-ethylsulfonyl-5-

(trifluoromethyl)pyridine:

Step 1 : Preparation of 1-[[3-chloro-5-(trifluoromethyl)pyridine-2-carbonyl]amino]-3-methyl-thiourea:

To a solution of 1-amino-3-methyl-thiourea (1.94 g, 18.44 mmol) in pyridine (2.5 ml) and

dichloromethane (35 ml) at 10°C was added a solution of 3-chloro-5-(trifluoromethyl)pyridine-2- carbonyl chloride (5.0 g, 20.49 mmol) in dichloromethane (15 ml) dropewise over one hour. The reaction mixture was stirred overnight at room temperature, then concentrated under reduced pressure. The residue was treated with water (50 ml), the suspension filtered and the solid washed with cold water. The crude material was dissolved in ethyl acetate, dried over sodium sulfate and concentrated to afford the title compound (3.4 g) as a pale yellow solid, mp 181-182°C. This material was used without further purification. LCMS (method 3): 313/315 (M+H)⁺, retention time 0.83 min. H- NMR (methanol-d4, ppm) 3.05 (3H), 8.43 (1 H), 8.91 (1 H).

Step 2: Preparation of 3-[3-chloro-5-(trifluoromethyl)-2-pyridyl]-4-methyl-1 H-1 ,2,4-triazole-5-thione;

A stirred suspension of 1-[[3-chloro-5-(trifluoromethyl)pyridine-2-carbonyl]amino]-3-methyl-thiourea (1.0 g, 3.20 mmol) in aqueous 2M sodium bicarbonate (20 ml) was slowly heated to reflux. After refluxing overnight, the reaction mixture was cooled, filtered and the clear yellow filtrate carefully acidified by dropwise addition of concentrated hydrochloric acid at 0°C. The resulting solid was collected by filtration, washed with cold water, dissolved in ethyl acetate, the solution dried over sodium sulfate and concentrated to afford the title compound (720 mg) as a pale yellow solid, mp 226- 228°C. This material was used without further purification. LCMS (method 3): 295/297 (M+H)⁺, retention time 1 .1 1 min. Ή-NMR (DMSO-d6, ppm) 3.52 (3H), 8.79 (1 H), 9.16 (1 H), 14.31 (1 H).

Step 3: Preparation of 3-chloro-2-(4-methyl-1 ,2,4-triazol-3-yl)-5-(trifluoromethyl)pyridine

A suspension of 3-[3-chloro-5-(trifluoromethyl)-2-pyridyl]-4-methyl-1 H-1 ,2,4-triazole-5-thione (500 mg, 1.70 mmol) in a mixture of 65% nitric acid (2 ml) and water (15 ml) was warmed gently (caution!). After a short induction period, gas evolution was observed. The reaction was completed by slowly increasing the temperature and heating at reflux for one hour. The reaction mixture was cooled to 10°C and basified by addition of aqueous 30% sodium hydroxide. The suspension was filtered and the solid washed with cold water. The aqueous filtrate was extracted with dichloromethane (3x) and the previously obtained solid dissolved in the separated organic layer. This dichloromethane layer was dried over sodium sulfate and concentrated to afford the title compound (350 mg) as a solid, mp 130- 131 .5°C. This material was used without further purification. LCMS (method 3): 263/265 (M+H)⁺, retention time 0.82 min. Ή-NMR (CDCb, ppm) 3.88 (3H), 8.17 (1 H), 8.29 (1 H), 8.88 (1 H).

Step 4: Preparation of 3-ethylsulfanyl-2-(4-methyl-1 ,2,4-triazol-3-yl)-5-(trifluoromethyl)pyridi s ) To a solution of 3-chloro-2-(4-methyl-1 ,2,44riazol-3-yl)-5-(trifluoromethyl)pyridine (25.0 g, 95.19 mmol) in dry N,N-dimethylformamide (200 ml) at 0-5°C was added sodium ethanethiolate (18.9 g, 90%, 199.8 mmol) in four portions and the mixture was stirred at 0-5°C for 30 minutes, then at room temperature for 3 hours. The solvent was removed under reduced pressure, the solid residue treated with water (250 ml), the suspension filtered and the solid washed with cold water (4x 100 ml). The crude material was dissolved in dichloromethane, dried over sodium sulfate and concentrated to afford the title compound (26.3 g) as a pale yellow solid, mp 165-166°C. This material was used without further purification. LCMS (method 3): 289 (M+H)⁺, retention time 1.08 min. Ή-NMR (CDCb, ppm) 1.40 (3H), 3.01 (2H), 3.94 (3H), 7.88 (1 H), 8.25 (1 H), 8.66 (1 H). Step 5: Preparation of 3-ethylsulfonyl-2-(4-methyl-1 ,2,4-triazol-3-yl)-5-(trifluoromethyl)pyridine

To a solution of 3-ethylsulfanyl-2-(4-methyl-1 ,2,4-triazol-3-yl)-5-(trifluoromethyl)pyridine (24.0 g, 83.25 mmol) in dichloromethane (300 ml) at 10°C was added mCPBA (75 wt% in water) (40.22 g, 174.8 mmol, 75%) in six portions and the mixture was stirred at room temperature overnight. The reaction mixture was filtered, the filtrate washed with an aqueous 10% sodium thiosulfate solution (3x), then with sat. aqueous NaHCC (4x) and brine, dried over sodium sulfate and concentrated to afford the title compound (25.5 g) as a white solid, mp 185-187°C. This material was used without further purification. LCMS (method 3): 321 (M+H)⁺, retention time 0.85 min. Ή-NMR (CDCb, ppm) 1.39 (3H), 3.75 (3H), 3.94 (2H), 8.28 (1 H), 8.76 (1 H), 9.19 (1 H). Step 6: Preparation of 2-(5-bromo-4-methyl-1 ,2,4-triazol-3-yl)-3-ethylsulfonyl-5- (trifluoromethyl)pyridine

To a solution of 3-ethylsulfonyl-2-(4-methyl-1 ,2,4-triazol-3-yl)-5-(trifluoromethyl)pyridine (15.0 g, 46.8 mmol) in acetonitrile (250 ml) was added N-bromo succinimide (20.84 g, 1 17.1 mmol) and the mixture was heated at reflux temperature overnight. The reaction mixture was concentrated and the residue diluted with dichloromethane, washed with saturated aqueous sodium bicarbonate, brine, dried over magnesium sulfate and concentrated. The residue was purified over silica by flash column chromatography (cyclohexane/ethyl acetate 3: 1 ) to afford the title compound (15.5 g) as a solid, mp 172-173°C. LCMS (method 3): 399/401 (M+H)⁺, retention time 1.1 1 min. Ή-NMR (CDCb, ppm) 1.39 (3H), 3.67 (3H), 3.89 (2H), 8.75 (1 H), 9.20 (1 H).

EXAMPLE P3: Preparation of 2-(5-bromo-4-methyl-1 ,2,4-triazol-3-yl)-3-ethylsulfanyl-5-

(trifluoromethyl)pyridine:

Obtained from 3-ethylsulfanyl-2-(4-methyl-1 ,2,4-triazol-3-yl)-5-(trifluoromethyl)pyridine (100 mg, 0.347 mmol) and N-bromo succinimide (61 mg, 0.343 mmol) in carbon tetrachloride (0.3 ml) according to procedure Example P2, step 6. The mixture was stirred at reflux temperature for 30 minutes.

Combiflash purification afforded the title compound (66 mg) as a solid. LCMS (method 4): 367/369 (M+H)⁺, retention time 0.91 min. Ή-NMR (CDCb, ppm) 1.39 (3H), 3.01 (2H), 3.85 (3H), 7.89 (1 H),

8.67 (1 H).

EXAMPLE P4: Preparation of 3-ethylsulfonyl-2-[4-methyl-5-[4-(trifluoromethyl)imidazol-1-yll-1 ,2,4- triazol-3-vH-5-(trifluoromethyl)pyridine (compound P4):

Step 1 : Preparation of 3-ethylsulfanyl-2-[4-methyl-5-[4-(trifluoromethyl)imidazol-1-yl]-1 ,2,4-triazol-3-yl]- 5-(trifluoromethyl)pyridine (compound P2

Sodium hydride (7.91 mg, 0.198 mmol, 60% in mineral oil) was added to a solution of 4- (trifluoromethyl)-I H-imidazole (24.46 mg, 0.180 mmol) in dry N,N-dimethylformamide (0.4 ml). The reaction was stirred at room temperature for 30 minutes until gas evolution ceased. A solution of 2-(5- bromo-4-methyl-1 ,2,4-triazol-3-yl)-3-ethylsulfanyl-5-(trifluoromethyl)pyridine (66.0 mg, 0.180 mmol) in N,N-dimethylformamide (2.0 ml) was slowly added and the reaction mixture stirred at room

temperature for 30 minutes. Two more equivalents of the previously described solution consisting of sodium hydride and 4-(trifluoromethyl)-1 H-imidazole were then added and stirring continued overnight at 60°C. The mixture was quenched over water and ethyl acetate, the layers separated, the aqueous phase extracted twice with ethyl acetate, the combined organic phases dried over sodium sulfate and concentrated. The residue was purified over silica by flash column chromatography (cyclohexane/ethyl acetate) to afford 3-ethylsulfanyl-2-[4-methyl-5-[4-(trifluoromethyl)imidazol-1-yl]-1 ,2,4-triazol-3-yl]-5- (trifluoromethyl)pyridine (compound P2) as a solid (55 mg). LCMS (method 4): 423 (M+H)⁺, retention time 0.97 min. H-NMR (CDCb, ppm) 8.70 (t, 1 H), 8.00 (d, 1 H), 7.94 (d, 1 H), 7.71 (m, 1 H), 3.81 (s, 3H), 3.06 (q, 2H), 1.42 (t, 3H).

Step 2: Preparation of 3-ethylsulfonyl-2-[4-methyl-5-[4-(trifluoromethyl)inriidazol-1-yl]-1 ,2,4-triazol-3-yl]- 5-(trifluoromethyl)pyridine (title compound P4)

To a solution of 3-ethylsulfanyl-2-[4-methyl-5-[4-(trifluoromethyl)imidazol-1-yl]-1 ,2,4-triazol-3-yl]-5- (trifluoromethyl)pyridine (55.0 mg, 0.13 mmol) in dichloromethane (2.5 ml) was added mCPBA (70 wt% in water) (77.04 mg, 0.3125 mmol) in one portion and the mixture was stirred at room

temperature overnight. The reaction mixture was diluted with dichloromethane and an aqueous saturated solution of potassium carbonate. After separation, the aqueous layer was extracted twice with ethyl acetate, the combined organic layers dried over sodium sulfate and concentrated. The solid residue was purified over silica by flash column chromatography (cyclohexane/ethyl actate) to give 3- ethylsulfonyl-2-[4-methyl-5-[4-(trifluoromethyl)imidazol-1-yl]-1 ,2,4-triazol-3-yl]-5-trifluoromethyl)pyridine (compound P4) as a solid (25 mg). LCMS (method 4): 455 (M+H)⁺, retention time 0.89 min. H-NMR (CDCb, ppm) 9.25 (d, 1 H), 8.79 (d, 1 H), 8.03 (d, 1 H), 7.74 (t, 1 H), 3.89 (q, 2H), 3.64 (s, 3H), 1.42 (t,

3H).

EXAMPLE P5: Preparation of 3-ethylsulfonyl-2-[4-methyl-5-[5-(trifluoromethyl)-2-thienyll-1 ,2,4-triazol- 3-yll-5-(trifluoromethyl)pyridine (compound P8):

In a microwave vial, a mixture of 2-(5-bromo-4-methyl-1 ,2,4-triazol-3-yl)-3-ethylsulfonyl-5-

(trifluoromethyl)pyridine (200 mg, 0.50 mmol), [5-(trifluoromethyl)-2-thienyl]boronic acid (147 mg, 0.75 mmol) in 1 ,2-dimethoxyethane (3 ml) and aqueous 2M sodium carbonate (0.75 ml, 1.50 mmol) was flushed with argon for 5 minutes. Bis(triphenylphosphine)palladium(ll) dichloride (3.5 mg, 0.0050 mmol) was added, the vial was closed and heated in the microwave at 1 10°C for 30 minutes. The reaction mixture was diluted with dichloromethane and washed with water, brine, dried over sodium sulfate and concentrated. The residue was purified over silica by flash column chromatography (cyclohexane/ethyl acetate 3:1 ) to afford the title compound P8 (76 mg) as a solid, mp 157-159°C. LCMS (method 3): 471 (M+H)⁺, retention time 1 .63 min. Ή-NMR (CDCb, ppm) 1.41 (t, 3H), 3.84 (s, 3H), 3.95 (q, 2H), 7.54 (m, 2H), 8.78 (m, 1 H), 9.23 (s, 1 H).

EXAMPLE P6: General preparation method of 2-(5-heterocvclyl-4-methyl-1 ,2,4-triazol-3-yl)-3- ethylsulfonyl-5-(trifluoromethyl)pyridines

Sodium hydride (60 mg, 1 mmol, 60% in mineral oil) was added to a solution of the heterocycle Het- NH (1 mmol) in dry N,N-dimethylformamide (3 ml). The reaction was stirred at room temperature for 30 minutes until gas evolution ceased, then 2-(5-bromo-4-methyl-1 ,2,4-triazol-3-yl)-3-ethylsulfonyl-5- (trifluoromethyl)pyridine (0.5 mmol) was slowly added and the reaction mixture stirred at 80-130°C for 1-15 hours. The mixture was quenched over water and ethyl acetate, the layers separated, the aqueous phase extracted twice with ethyl acetate, the combined organic phases dried over sodium 62ulphate and concentrated. The residue was purified by C18 reversed-phase column

chromatography (acetonitrile gradient in water). Table G1 : Examples of 2-(5-heterocvclyl-4-methyl-1 ,2,4-triazol-3-yl)-3-ethylsulfonyl-5-

(trifluoromethyl)pyridines (compounds of formula (I)) prepared according to the general preparation method described above

Compound Reaction

Structures Het-NH NMR (400 MHz, CDCIs) No. conditions

F 9.26 (d, 1 H), 9.07(d, 1 H),

P7 130°C for 1 h 8.79 (t, 1 H),3.90 (s, 3H),

3.88 (g, 2H), 1.42 (t, 3H).

9.24 (t, 1 H), 8.78 (d, 1 H),

°*> 8.64 (s, 1 H), 8.03 (s, 1 H),

P5 80°C for 15 h

3.92 (s, 3H), 3.90 (g, 2H), 1.41 (t, 3H).

9.24 (d, 1 H), 8.78 (t, 1 H), 8.42 (dd, 1 H), 6.82 (d, 1 H),

P1 80°C for 15 h

F \_-/ 3.94 (s, 3H), 3.91 (g, 2H),

1.41 (t, 3H). Compound Reaction

Structures Het-NH NMR (400 MHz, CDCIs) No. conditions

Selected signals: 1.39 (t, 3H), 3.57 (s, 3H), 4.01 (q,

P6 80 °C for 1 h

2H), 8.74 (m, 1 H), 9.14 (m, 1 H).

Table P1 : Examples of compounds of formula (I)

LCMS

Compound

Structures Rt [ +H]⁺ Mp (°C)

No. Method

(min) (measured)

P1 1.00 455 4 solid

P2 0.97 423 4 solid

P3 1.19 416 5

P4 0.89 455 4 solid

P5 0.98 455 4 solid

LCMS

Compound

Structures Rt [ +H]⁺ Mp (°C) No. Method

(min) (measured)

P6 0.90 458 4 solid

P7 0.96 456 4 solid

P8 1.63 471 3 157-159

P9 0.97 457 4

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. 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 1 to 12 and P1 of the present invention"):

an adjuvant selected from the group of substances consisting of petroleum oils (628) + TX, an acaricide selected from the group of substances consisting of 1 , 1-bis(4-chlorophenyl)-2- ethoxyethanol (lUPAC name) (910) + TX, 2,4-dichlorophenyl benzenesulfonate (lUPAC/Chemical Abstracts name) (1059) + TX, 2-fluoro-A/-methyl-A/-1-naphthylacetamide (lUPAC name) (1295) + TX, 4-chlorophenyl phenyl sulfone (lUPAC 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 (lUPAC name) (888) + TX, azocyclotin (46) + TX, azothoate (889) + TX, benomyl (62) + TX, benoxafos [CCN] + TX, benzoximate (71 ) + TX, benzyl benzoate (lUPAC name) [CCN] + TX, bifenazate (74) + TX, bifenthrin (76) + TX, binapacryl (907) + TX, brofenvalerate + TX, bromocyclen (918) + TX, bromophos (920) + TX, bromophos-ethyl (921 ) + TX, bromopropylate (94) + TX, buprofezin (99) + TX, butocarboxim (103) + TX, butoxycarboxim (104) + TX, butylpyridaben + TX, calcium polysulfide (lUPAC name) (1 1 1 ) + TX, camphechlor (941 ) + TX, carbanolate (943) + TX, carbaryl (1 15) + TX, carbofuran (1 18) + 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 [CCN] + TX, coumaphos (174) + TX, crotamiton [CCN] + TX, crotoxyphos (1010) + TX, cufraneb (1013) + TX, cyanthoate (1020) + TX, cyflumetofen (CAS Reg. No.: 400882-07-7) + TX, cyhalothrin (196) + TX, cyhexatin (199) + TX, cypermethrin (201 ) + TX, DCPM (1032) + TX, DDT (219) + TX, demephion (1037) + TX, demephion-O (1037) + TX, demephion-S (1037) + TX, demeton (1038) + TX, demeton-methyl (224) + TX, demeton-0 (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 + TX, dicofol (242) + TX, dicrotophos (243) + TX, dienochlor (1071 ) + TX, dimefox (1081 ) + TX, dimethoate (262) + TX, dinactin (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 (1 102) + TX, diphenyl sulfone (lUPAC name) (1 103) + TX, disulfiram [CCN] + TX, disulfoton (278) + TX, DNOC (282) + TX, dofenapyn (1 1 13) + TX, doramectin [CCN] + TX, endosulfan (294) + TX, endothion (1 121 ) + TX, EPN (297) + TX, eprinomectin [CCN] + TX, ethion (309) + TX, ethoate-methyl (1 134) + TX, etoxazole (320) + TX, etrimfos (1 142) + TX, fenazaflor (1 147) + TX, fenazaquin (328) + TX, fenbutatin oxide (330) + TX, fenothiocarb (337) + TX, fenpropathrin (342) + TX, fenpyrad + TX, fenpyroximate (345) + TX, fenson (1 157) + TX, fentrifanil (1 161 ) + TX, fenvalerate (349) + TX, fipronil (354) + TX, fluacrypyrim (360) + TX, fluazuron (1 166) + TX, flubenzimine (1 167) + TX, flucycloxuron (366) + TX, flucythrinate (367) + TX, fluenetil (1 169) + TX, flufenoxuron (370) + TX, flumethrin (372) + TX, fluorbenside (1 174) + TX, fluvalinate (1 184) + TX, FMC 1 137 (development code) (1 185) + TX, formetanate (405) + TX, formetanate hydrochloride (405) + TX, formothion (1 192) + TX, formparanate (1 193) + TX, gamma-HCH (430) + TX, glyodin (1205) + TX, halfenprox (424) + TX, heptenophos (432) + TX, hexadecyl cyclopropanecarboxylate (lUPAC/Chemical Abstracts name) (1216) + TX, hexythiazox (441 ) + TX, iodomethane (lUPAC name) (542) + TX, isocarbophos (473) + TX, isopropyl 0- (methoxyaminothiophosphoryl)salicylate (lUPAC name) (473) + TX, ivermectin [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 [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 [CCN] + TX, mipafox (1293) + TX, monocrotophos (561 ) + TX, morphothion (1300) + TX, moxidectin [CCN] + TX, naled (567) + TX, NC-184 (compound code) + TX, NC-512 (compound code) + TX, nifluridide (1309) + TX, nikkomycins [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 (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 (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 (71 1 ) + TX, quintiofos (1381 ) + TX, R-1492 (development code) (1382) + TX, RA-17 (development code) (1383) + TX, rotenone (722) + TX, schradan (1389) + TX, sebufos + TX, selamectin [CCN] + TX, SI-0009 (compound code) + TX, sophamide (1402) + TX, spirodiclofen (738) + TX, spiromesifen (739) + TX, SSI-121 (development code) (1404) + TX, sulfiram [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 + TX, tetrachlorvinphos (777) + TX, tetradifon (786) + TX, tetranactin (653) + TX, tetrasul (1425) + TX, thiafenox + TX, thiocarboxime (1431 ) + TX, thiofanox (800) + TX, thiometon (801 ) + TX, thioquinox (1436) + TX, thuringiensin [CCN] + TX, triamiphos (1441 ) + TX, triarathene (1443) + TX, triazophos (820) + TX, triazuron + TX, trichlorfon (824) + TX, trifenofos (1455) + TX, trinactin (653) + TX, vamidothion (847) + TX, vaniliprole [CCN] and YI-5302

(compound code) + TX,

an algicide selected from the group of substances consisting of bethoxazin [CCN] + TX, copper dioctanoate (lUPAC name) (170) + TX, copper sulfate (172) + TX, cybutryne [CCN] + TX, dichlone (1052) + TX, dichlorophen (232) + TX, endothal (295) + TX, fentin (347) + TX, hyd rated lime [CCN] + TX, nabam (566) + TX, quinoclamine (714) + TX, quinonamid (1379) + TX, simazine (730) + TX, triphenyltin acetate (lUPAC name) (347) and triphenyltin hydroxide (lUPAC name) (347) + TX,

an anthelmintic selected from the group of substances consisting of abamectin (1 ) + TX, crufomate (101 1 ) + TX, doramectin [CCN] + TX, emamectin (291 ) + TX, emamectin benzoate (291 ) + TX, eprinomectin [CCN] + TX, ivermectin [CCN] + TX, milbemycin oxime [CCN] + TX, moxidectin [CCN] + TX, piperazine [CCN] + TX, selamectin [CCN] + TX, spinosad (737) and thiophanate (1435) + TX,

an avicide selected from the group of substances consisting of chloralose (127) + TX, endrin (1 122) + TX, fenthion (346) + TX, pyridin-4-amine (lUPAC name) (23) and strychnine (745) + TX, a bactericide selected from the group of substances consisting of 1-hydroxy-1 /- -pyridine-2-thione (lUPAC name) (1222) + TX, 4-(quinoxalin-2-ylamino)benzenesulfonamide (lUPAC name) (748) + TX, 8-hydroxyquinoline sulfate (446) + TX, bronopol (97) + TX, copper dioctanoate (lUPAC name) (170) + TX, copper hydroxide (lUPAC name) (169) + TX, cresol [CCN] + TX, dichlorophen (232) + TX, dipyrithione (1 105) + TX, dodicin (1 1 12) + TX, fenaminosulf (1 144) + TX, formaldehyde (404) + TX, hydrargaphen [CCN] + TX, kasugamycin (483) + TX, kasugamycin hydrochloride hydrate (483) + TX, nickel bis(dimethyldithiocarbamate) (lUPAC name) (1308) + TX, nitrapyrin (580) + TX, octhilinone (590) + TX, oxolinic acid (606) + TX, oxytetracycline (61 1 ) + TX, potassium

hydroxyquinoline sulfate (446) + TX, probenazole (658) + TX, streptomycin (744) + TX,

streptomycin sesquisulfate (744) + TX, tecloftalam (766) + TX, and thiomersal [CCN] + TX, a biological agent selected from the group of substances consisting of Adoxophyes orana GV (12) + TX, Agrobacterium radiobacter (13) + TX, Amblyseius spp. (19) + TX, Anagrapha falcifera NPV (28) + TX, Anagrus atomus (29) + TX, Aphelinus abdominalis (33) + TX, Aphidius colemani (34) + TX, Aphidoletes aphidimyza (35) + TX, Autographa californica NPV (38) + TX, Bacillus firmus (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 (53) + TX, Beauveria brongniartii (54) + TX, Chrysoperla carnea (151 ) + TX, Cryptolaemus montrouzieri (178) + TX, Cydia pomonella GV (191 ) + TX, Dacnusa sibirica (212) + TX, Diglyphus isaea (254) + TX, Encarsia formosa (scientific name) (293) + TX, Eretmocerus eremicus (300) + TX, Helicoverpa zea NPV (431 ) + TX, Heterorhabditis bacteriophora and H. megidis (433) + TX, Hippodamia convergens (442) + TX, Leptomastix dactylopii (488) + TX, Macrolophus caliginosus (491 ) + TX, Mamestra brassicae NPV (494) + TX, Metaphycus helvolus (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 (575) + TX, Onus spp. (596) + TX, Paecilomyces fumosoroseus (613) + TX, Phytoseiulus persimilis (644) + TX,

Spodoptera exigua multicapsid nuclear polyhedrosis virus (scientific name) (741 ) + TX, Steinernema bibionis (742) + TX, Steinernema carpocapsae (742) + TX, Steinernema feltiae (742) + TX, Steinernema glaseri (742) + TX, Steinernema riobrave (742) + TX, Steinernema riobravis (742) + TX, Steinernema scapterisci (742) + TX, Steinernema spp. (742) + TX, Trichogramma spp. (826) + TX, Typhlodromus occidentalis (844) and Verticillium lecanii (848) + TX,

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

a chemosterilant selected from the group of substances consisting of apholate [CCN] + TX, bisazir [CCN] + TX, busulfan [CCN] + TX, diflubenzuron (250) + TX, dimatif [CCN] + TX, hemel [CCN] + TX, hempa [CCN] + TX, metepa [CCN] + TX, methiotepa [CCN] + TX, methyl apholate [CCN] + TX, morzid [CCN] + TX, penfluron [CCN] + TX, tepa [CCN] + TX, thiohempa [CCN] + TX, thiotepa [CCN] + TX, tretamine [CCN] and uredepa [CCN] + TX,

an insect pheromone selected from the group of substances consisting of (E)-dec-5-en-1-yl acetate with (E)-dec-5-en-1-ol (lUPAC name) (222) + TX, (E)-tridec-4-en-1-yl acetate (lUPAC name) (829) + TX, (E)-6-methylhept-2-en-4-ol (lUPAC name) (541 ) + TX, (E,Z)-tetradeca-4, 10-dien-1-yl acetate (lUPAC name) (779) + TX, (Z)-dodec-7-en-1-yl acetate (lUPAC name) (285) + TX, (Z)-hexadec-l 1- enal (lUPAC name) (436) + TX, (Z)-hexadec-l 1-en-1-yl acetate (lUPAC name) (437) + TX, (Z)- hexadec-13-en-1 1-yn-1-yl acetate (lUPAC name) (438) + TX, (Z)-icos-13-en-10-one (lUPAC name) (448) + TX, (Z)-tetradec-7-en-1-al (lUPAC name) (782) + TX, (Z)-tetradec-9-en-1-ol (lUPAC name) (783) + TX, (Z)-tetradec-9-en-1-yl acetate (lUPAC name) (784) + TX, (7E,9Z)-dodeca-7,9-dien-1-yl acetate (lUPAC name) (283) + TX, (9Z, 1 1 E)-tetradeca-9, 1 1-dien-1-yl acetate (lUPAC name) (780) + TX, (9Z, 12E)-tetradeca-9, 12-dien-1-yl acetate (lUPAC name) (781 ) + TX, 14-methyloctadec-1-ene (lUPAC name) (545) + TX, 4-methylnonan-5-ol with 4-methylnonan-5-one (lUPAC name) (544) + TX, alpha-multistriatin [CCN] + TX, brevicomin [CCN] + TX, codlelure [CCN] + TX, codlemone (167) + TX, cuelure (179) + TX, disparlure (277) + TX, dodec-8-en-1-yl acetate (lUPAC name) (286) + TX, dodec-9-en-1-yl acetate (lUPAC name) (287) + TX, dodeca-8 + TX, 10-dien-1-yl acetate (lUPAC name) (284) + TX, dominicalure [CCN] + TX, ethyl 4-methyloctanoate (lUPAC name) (317) + TX, eugenol [CCN] + TX, frontalin [CCN] + TX, gossyplure (420) + TX, grandlure (421 ) + TX, grandlure I (421 ) + TX, grandlure II (421 ) + TX, grandlure III (421 ) + TX, grandlure IV (421 ) + TX, hexalure [CCN] + TX, ipsdienol [CCN] + TX, ipsenol [CCN] + TX, japonilure (481 ) + TX, lineatin [CCN] + TX, litlure [CCN] + TX, looplure [CCN] + TX, medlure [CCN] + TX, megatomoic acid [CCN] + TX, methyl eugenol (540) + TX, muscalure (563) + TX, octadeca-2, 13-dien-1-yl acetate (lUPAC name) (588) + TX, octadeca-3, 13-dien-1-yl acetate (lUPAC name) (589) + TX, orfralure [CCN] + TX, oryctalure (317) + TX, ostramone [CCN] + TX, siglure [CCN] + TX, sordidin (736) + TX, sulcatol [CCN] + TX, tetradec-11-en-1-yl acetate (lUPAC name) (785) + TX, trimedlure (839) + TX, trimedlure A (839) + TX, trimedlure Bi (839) + TX, trimedlure B₂ (839) + TX, trimedlure C (839) and trunc-call [CCN] + TX,

an insect repellent selected from the group of substances consisting of 2-(octylthio)ethanol (lUPAC name) (591 ) + TX, butopyronoxyl (933) + TX, butoxy(polypropylene glycol) (936) + TX, dibutyl adipate (lUPAC name) (1046) + TX, dibutyl phthalate (1047) + TX, dibutyl succinate (lUPAC name) (1048) + TX, diethyltoluamide [CCN] + TX, dimethyl carbate [CCN] + TX, dimethyl phthalate [CCN] + TX, ethyl hexanediol (1 137) + 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

(lUPAC/Chemical Abstracts name) (1058) + TX, 1 , 1-dichloro-2,2-bis(4-ethylphenyl)ethane (lUPAC name) (1056), + TX, 1 ,2-dichloropropane (lUPAC/Chemical Abstracts name) (1062) + TX, 1 ,2- dichloropropane with 1 ,3-dichloropropene (lUPAC name) (1063) + TX, 1-bromo-2-chloroethane (lUPAC/Chemical Abstracts name) (916) + TX, 2,2,2-trichloro-1-(3,4-dichlorophenyl)ethyl acetate (lUPAC name) (1451 ) + TX, 2,2-dichlorovinyl 2-ethylsulfinylethyl methyl phosphate (lUPAC name) (1066) + TX, 2-(1 ,3-dithiolan-2-yl)phenyl dimethylcarbamate (lUPAC/ Chemical Abstracts name) (1 109) + TX, 2-(2-butoxyethoxy)ethyl thiocyanate (lUPAC/Chemical Abstracts name) (935) + TX, 2- (4,5-dimethyl-1 ,3-dioxolan-2-yl)phenyl methylcarbamate (lUPAC/ Chemical Abstracts name) (1084) + TX, 2-(4-chloro-3,5-xylyloxy)ethanol (lUPAC name) (986) + TX, 2-chlorovinyl diethyl phosphate

(lUPAC name) (984) + TX, 2-imidazolidone (lUPAC name) (1225) + TX, 2-isovalerylindan-1 ,3-dione (lUPAC name) (1246) + TX, 2-methyl(prop-2-ynyl)aminophenyl methylcarbamate (lUPAC name) (1284) + TX, 2-thiocyanatoethyl laurate (lUPAC name) (1433) + TX, 3-bromo-1-chloroprop-1-ene (lUPAC name) (917) + TX, 3-methyl-1-phenylpyrazol-5-yl dimethylcarbamate (lUPAC name) (1283) + TX, 4-methyl(prop-2-ynyl)amino-3,5-xylyl methylcarbamate (lUPAC name) (1285) + TX, 5,5-dimethyl- 3-oxocyclohex-1-enyl dimethylcarbamate (lUPAC name) (1085) + TX, abamectin (1 ) + TX, acephate (2) + TX, acetamiprid (4) + TX, acethion [CCN] + TX, acetoprole [CCN] + TX, acrinathrin (9) + TX, acrylonitrile (lUPAC name) (861 ) + TX, alanycarb (15) + TX, aldicarb (16) + TX, aldoxycarb (863) + TX, aldrin (864) + TX, allethrin (17) + TX, allosamidin [CCN] + TX, allyxycarb (866) + TX, alpha-cypermethrin (202) + TX, alpha-ecdysone [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 (41 ) + TX, azamethiphos (42) + TX, azinphos-ethyl (44) + TX, azinphos-methyl (45) + TX, azothoate (889) + TX, Bacillus thuringiensis delta endotoxins (52) + TX, barium

hexafluorosilicate [CCN] + TX, barium polysulfide (lUPAC/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 (79) + TX, bioethanomethrin [CCN] + TX, biopermethrin (908) + TX, bioresmethrin (80) + TX, bis(2-chloroethyl) ether (lUPAC name) (909) + TX, bistrifluron (83) + TX, borax (86) + TX, brofenvalerate + TX, bromfenvinfos (914) + TX, bromocyclen (918) + TX, bromo-DDT [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 + TX, cadusafos (109) + TX, calcium arsenate [CCN] + TX, calcium cyanide (444) + TX, calcium polysulfide (lUPAC name) (1 1 1 ) + TX, camphechlor (941 ) + TX, carbanolate (943) + TX, carbaryl (1 15) + TX, carbofuran (1 18) + TX, carbon disulfide (lUPAC/Chemical Abstracts name) (945) + TX, carbon tetrachloride (lUPAC name) (946) + TX, carbophenothion (947) + TX, carbosulfan (1 19) + TX, cartap (123) + TX, cartap hydrochloride (123) + TX, cevadine (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 + TX, cismethrin (80) + TX, clocythrin + TX, cloethocarb (999) + TX, closantel [CCN] + TX, clothianidin (165) + TX, copper acetoarsenite

[CCN] + TX, copper arsenate [CCN] + TX, copper oleate [CCN] + TX, coumaphos (174) + TX, coumithoate (1006) + TX, crotamiton [CCN] + TX, crotoxyphos (1010) + TX, crufomate (101 1 ) + TX, cryolite (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 [CCN] + TX, cf-limonene [CCN] + TX, cf-tetramethrin (788) + TX, DAEP (1031 ) + TX, dazomet (216) + TX, DDT (219) + TX, decarbofu ran (1034) + TX, deltamethrin (223) + TX, demephion (1037) + TX, demephion-0 (1037) + TX, demephion-S (1037) + TX, demeton (1038) + TX, demeton-methyl (224) + TX, demeton-0 (1038) + TX, demeton-O- methyl (224) + TX, demeton-S (1038) + TX, demeton-S-methyl (224) + TX, demeton-S- methylsulphon (1039) + TX, diafenthiuron (226) + TX, dialifos (1042) + TX, diamidafos (1044) + TX, diazinon (227) + TX, dicapthon (1050) + TX, dichlofenthion (1051 ) + TX, dichlorvos (236) + TX, dicliphos + TX, dicresyl [CCN] + TX, dicrotophos (243) + TX, dicyclanil (244) + TX, dieldrin (1070) + TX, diethyl 5-methylpyrazol-3-yl phosphate (lUPAC name) (1076) + TX, diflubenzuron (250) + TX, dilor [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 (1 100) + TX, dioxacarb (1 101 ) + TX, dioxathion (1 102) + TX, disulfoton (278) + TX, dithicrofos (1 108) + TX, DNOC (282) + TX, doramectin [CCN] + TX, DSP (1 1 15) + TX, ecdysterone [CCN] + TX, El 1642 (development code) (1 1 18) + TX, emamectin (291 ) + TX, emamectin benzoate (291 ) + TX, EMPC (1 120) + TX, empenthrin (292) + TX, endosulfan (294) + TX, endothion (1 121 ) + TX, endrin (1 122) + TX, EPBP (1 123) + TX, EPN (297) + TX, epofenonane (1 124) + TX, eprinomectin [CCN] + TX, esfenvalerate (302) + TX, etaphos [CCN] + TX, ethiofencarb (308) + TX, ethion (309) + TX, ethiprole (310) + TX, ethoate-m ethyl (1 134) + TX, ethoprophos (312) + TX, ethyl formate (lUPAC name) [CCN] + TX, ethyl-DDD (1056) + TX, ethylene dibromide (316) + TX, ethylene dichloride (chemical name) (1 136) + TX, ethylene oxide [CCN] + TX, etofenprox (319) + TX, etrimfos (1 142) + TX, EXD (1 143) + TX, famphur (323) + TX, fenamiphos (326) + TX, fenazaflor (1 147) + TX, fenchlorphos (1 148) + TX, fenethacarb (1 149) + TX, fenfluthrin (1 150) + TX, fenitrothion (335) + TX, fenobucarb (336) + TX, fenoxacrim (1 153) + TX, fenoxycarb (340) + TX, fenpirithrin (1 155) + TX, fenpropathrin (342) + TX, fenpyrad + TX, fensulfothion (1 158) + 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 (1 168) + TX, flucycloxuron (366) + TX, flucythrinate (367) + TX, fluenetil (1 169) + TX, flufenerim [CCN] + TX, flufenoxuron (370) + TX, flufenprox (1 171 ) + TX, flumethrin (372) + TX, fluvalinate (1 184) + TX, FMC 1 137 (development code) (1 185) + TX, fonofos (1 191 ) + TX, formetanate (405) + TX, formetanate hydrochloride (405) + TX, formothion (1 192) + TX, formparanate (1 193) + TX, fosmethilan (1 194) + TX, fospirate (1 195) + TX, fosthiazate (408) + TX, fosthietan (1 196) + 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 (121 1 ) + 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 (lUPAC name) (542) + TX, IPSP (1229) + TX, isazofos (1231 ) + TX, isobenzan (1232) + TX, isocarbophos (473) + TX, isodrin (1235) + TX, isofenphos (1236) + TX, isolane (1237) + TX, isoprocarb (472) + TX, isopropyl 0-(methoxyaminothiophosphoryl)salicylate (lUPAC name) (473) + TX, isoprothiolane (474) + TX, isothioate (1244) + TX, isoxathion (480) + TX, ivermectin [CCN] + TX, jasmolin I (696) + TX, jasmolin II (696) + TX, jodfenphos (1248) + TX, juvenile hormone I [CCN] + TX, juvenile hormone II [CCN] + TX, juvenile hormone III [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 (lUPAC name) (1014) + TX, magnesium phosphide (lUPAC 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 (519) + TX, metam-sodium (519) + TX, methacrifos (1266) + TX, methamidophos (527) + TX, methanesulfonyl fluoride (lUPAC/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 (533) + TX, methoxychlor (534) + TX, methoxyfenozide (535) + TX, methyl bromide (537) + TX, methyl isothiocyanate (543) + TX, methylchloroform [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 [CCN] + TX, mipafox (1293) + TX, mirex (1294) + TX, monocrotophos (561 ) + TX, morphothion (1300) + TX, moxidectin [CCN] + TX, naftalofos [CCN] + TX, naled (567) + TX, naphthalene (lUPAC/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 (131 1 ) + 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, 0-5-dichloro-4-iodophenyl O-ethyl ethylphosphonothioate (lUPAC name) (1057) + TX, 0,0- diethyl 0-4-methyl-2-oxo-2A -chromen-7-yl phosphorothioate (lUPAC name) (1074) + TX, 0,0-diethyl 0-6-methyl-2-propylpyrimidin-4-yl phosphorothioate (lUPAC name) (1075) + TX, Ο,Ο,Ο',Ο'- tetrapropyl dithiopyrophosphate (lUPAC name) (1424) + TX, oleic acid (lUPAC 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 [CCN] + TX, pentachlorophenol (623) + TX, pentachlorophenyl laurate (lUPAC name) (623) + TX, permethrin (626) + TX, petroleum oils (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 (lUPAC 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 (lUPAC name) (1346) + TX, polychloroterpenes (traditional name) (1347) + TX, potassium arsenite [CCN] + TX, potassium thiocyanate [CCN] + TX, prallethrin (655) + TX, precocene I [CCN] + TX, precocene II [CCN] + TX, precocene III [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 [CCN] + TX, quinalphos (71 1 ) + TX, quinalphos-methyl (1376) + TX, quinothion (1380) + TX, quintiofos (1381 ) + TX, R-1492 (development code) (1382) + TX, rafoxanide [CCN] + TX, resmethrin (719) + TX, rotenone (722) + TX, RU 15525 (development code) (723) + TX, RU 25475 (development code) (1386) + TX, ryania (1387) + TX, ryanodine (traditional name) (1387) + TX, sabadilla (725) + TX, schradan (1389) + TX, sebufos + TX, selamectin [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 (lUPAC/Chemical Abstracts name) (1399) + TX, sodium hexafluorosilicate (1400) + TX, sodium pentachlorophenoxide (623) + TX, sodium selenate (lUPAC 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 (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 + TX, terbufos (773) + TX, tetrachloroethane [CCN] + TX, tetrachlorvinphos (777) + TX, tetramethrin (787) + TX, theta-cypermethrin (204) + TX, thiacloprid (791 ) + TX, thiafenox + 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 [CCN] + TX, tolfenpyrad (809) + TX, tralomethrin (812) + TX, transfluthrin (813) + TX, transpermethrin (1440) + TX, triamiphos (1441 ) + TX, triazamate (818) + TX, triazophos (820) + TX, triazuron + TX, trichlorfon (824) + TX, trichlormetaphos-3 [CCN] + TX, trichloronat (1452) + TX, trifenofos (1455) + TX, triflumuron (835) + TX, trimethacarb (840) + TX, triprene (1459) + TX, vamidothion (847) + TX, vaniliprole [CCN] + TX, veratridine (725) + TX, veratrine (725) + TX, XMC (853) + TX, xylylcarb (854) + TX, YI-5302 (compound code) + TX, zeta-cypermethrin (205) + TX, zetamethrin + 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 2012/0921 15) + 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

WO2005/077934) + TX,

a molluscicide selected from the group of substances consisting of bis(tributyltin) oxide (lUPAC 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 (lUPAC 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 (lUPAC name) (347) and triphenyltin hydroxide (lUPAC name) (347) + TX, pyriprole [394730-71-3] + TX,

a nematicide selected from the group of substances consisting of AKD-3088 (compound code) + TX, 1 ,2-dibromo-3-chloropropane (lUPAC/Chemical Abstracts name) (1045) + TX, 1 ,2-dichloropropane (lUPAC/ Chemical Abstracts name) (1062) + TX, 1 ,2-dichloropropane with 1 ,3-dichloropropene (lUPAC name) (1063) + TX, 1 ,3-dichloropropene (233) + TX, 3,4-dichlorotetrahydrothiophene 1 ,1- dioxide (lUPAC/Chemical Abstracts name) (1065) + TX, 3-(4-chlorophenyl)-5-methylrhodanine (lUPAC name) (980) + TX, 5-methyl-6-thioxo-1 ,3,5-thiadiazinan-3-ylacetic acid (lUPAC name) (1286) + TX, 6-isopentenylaminopurine (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 + TX, cadusafos (109) + TX, carbofuran (1 18) + TX, carbon disulfide (945) + TX, carbosulfan (1 19) + TX, chloropicrin (141 ) + TX, chlorpyrifos (145) + TX, cloethocarb (999) + TX, cytokinins (210) + TX, dazomet (216) + TX, DBCP (1045) + TX, DCIP (218) + TX, diamidafos (1044) + TX, dichlofenthion (1051 ) + TX, dicliphos + TX, dimethoate (262) + TX, doramectin [CCN] + TX, emamectin (291 ) + TX, emamectin benzoate (291 ) + TX, eprinomectin [CCN] + TX, ethoprophos (312) + TX, ethylene dibromide (316) + TX, fenamiphos (326) + TX, fenpyrad + TX, fensulfothion (1 158) + TX, fosthiazate (408) + TX, fosthietan (1 196) + TX, furfural [CCN] + TX, GY-81 (development code) (423) + TX, heterophos [CCN] + TX, iodomethane (lUPAC name) (542) + TX, isamidofos (1230) + TX, isazofos (1231 ) + TX, ivermectin [CCN] + TX, kinetin (210) + TX, mecarphon (1258) + TX, metam (519) + TX, metam-potassium (519) + TX, metam-sodium (519) + TX, methyl bromide (537) + TX, methyl isothiocyanate (543) + TX, milbemycin oxime [CCN] + TX, moxidectin [CCN] + TX, Myrothecium verrucaria composition (565) + TX, NC-184 (compound code) + TX, oxamyl (602) + TX, phorate (636) + TX, phosphamidon (639) + TX, phosphocarb [CCN] + TX, sebufos + TX, selamectin [CCN] + TX, spinosad (737) + TX, terbam + TX, terbufos (773) + TX, tetrachlorothiophene (lUPAC/ Chemical Abstracts name) (1422) + TX, thiafenox + TX, thionazin (1434) + TX, triazophos (820) + TX, triazuron + TX, xylenols [CCN] + TX, YI-5302 (compound code) and zeatin (210) + TX, fluensulfone [318290-98-1] + TX,

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

a plant activator selected from the group of substances consisting of acibenzolar (6) + TX, acibenzolar-S-methyl (6) + TX, probenazole (658) and Reynoutria sachalinensis extract (720) + TX, a rodenticide selected from the group of substances consisting of 2-isovalerylindan-1 ,3-dione (lUPAC name) (1246) + TX, 4-(quinoxalin-2-ylamino)benzenesulfonamide (lUPAC 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 (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 (1 183) + TX, flupropadine hydrochloride (1 183) + TX, gamma-HCH (430) + TX, HCH (430) + TX, hydrogen cyanide (444) + TX, iodomethane (lUPAC name) (542) + TX, lindane (430) + TX, magnesium phosphide (lUPAC name) (640) + TX, methyl bromide (537) + TX, norbormide (1318) + TX, phosacetim (1336) + TX, phosphine (lUPAC name) (640) + TX, phosphorus [CCN] + TX, pindone (1341 ) + TX, potassium arsenite [CCN] + TX, pyrinuron (1371 ) + TX, scilliroside (1390) + TX, sodium arsenite [CCN] + TX, sodium cyanide (444) + TX, sodium fluoroacetate (735) + TX, strychnine (745) + TX, thallium sulfate [CCN] + TX, warfarin (851 ) and zinc phosphide (640) + TX,

a synergist selected from the group of substances consisting of 2-(2-butoxyethoxy)ethyl piperonylate (lUPAC name) (934) + TX, 5-(1 ,3-benzodioxol-5-yl)-3-hexylcyclohex-2-enone (lUPAC name) (903) + TX, farnesol with nerolidol (324) + TX, MB-599 (development code) (498) + TX, MGK 264 (development code) (296) + TX, piperonyl butoxide (649) + TX, piprotal (1343) + TX, propyl isomer (1358) + TX, S421 (development code) (724) + TX, sesamex (1393) + TX, sesasmolin (1394) and sulfoxide (1406) + TX,

an animal repellent selected from the group of substances consisting of anthraquinone (32) + TX, chloralose (127) + TX, copper naphthenate [CCN] + TX, copper oxychloride (171 ) + TX, diazinon (227) + TX, dicyclopentadiene (chemical name) (1069) + TX, guazatine (422) + TX, guazatine acetates (422) + TX, methiocarb (530) + TX, pyridin-4-amine (lUPAC name) (23) + TX, thiram (804) + TX, trimethacarb (840) + TX, zinc naphthenate [CCN] and ziram (856) + TX,

a virucide selected from the group of substances consisting of imanin [CCN] and ribavirin [CCN] + TX,

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

and biologically active compounds selected from the group consisting of azaconazole (60207-31-0] + TX, bitertanol [70585-36-3] + TX, bromuconazole [1 16255-48-2] + TX, cyproconazole [94361-06-5] + TX, difenoconazole [1 19446-68-3] + TX, diniconazole [83657-24-3] + TX, epoxiconazole

[106325-08-0] + TX, fenbuconazole [1 14369-43-6] + 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 [1251 16-23-6] + TX, myclobutanil [88671-89-0] + TX, pefurazoate [101903-30-4] + TX, penconazole [66246-88-6] + TX, prothioconazole [178928-70-6] + TX, pyrifenox [88283-41-4] + TX, prochloraz [67747-09-5] + TX, propiconazole [60207-90-1] + TX, simeconazole [149508-90-7] + TX, tebuconazole [107534-96-3] + TX, tetraconazole [1 12281-77-3] + TX, triadimefon [43121-43-3] + TX, triad imenol [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 [1 18134-30-8] + TX, tridemorph [81412-43-3] + TX, cyprodinil [121552-61-2] + TX, mepanipyrim [1 10235-47-7] + TX, pyrimethanil [531 12-28-0] + TX, fenpiclonil [74738-17-3] + TX, fludioxonil [131341-86-1] + TX, benalaxyl [71626-1 1-4] + TX, furalaxyl [57646-30-7] + TX, meta- laxyl [57837-19-1] + TX, R-metalaxyl [70630-17-0] + TX, ofurace [58810-48-3] + TX, oxadixyl [77732-09-3] + TX, benomyl [17804-35-2] + TX, carbendazim [10605-21-7] + TX, debacarb

[62732-91-6] + TX, fuberidazole [3878-19-1] + TX, thiabendazole [148-79-8] + TX, chlozolinate [84332-86-5] + TX, dichlozoline [24201-58-9] + TX, iprodione [36734-19-7] + TX, myclozoline [54864-61-8] + TX, procymidone [32809-16-8] + TX, vinclozoline [50471-44-8] + TX, boscalid [188425-85-6] + TX, carboxin [5234-68-4] + TX, fenfuram [24691-80-3] + TX, flutolanil [66332-96- 5] + TX, mepronil [55814-41-0] + TX, oxycarboxin [5259-88-1] + TX, penthiopyrad [183675-82-3] + TX, thifluzamide [130000-40-7] + TX, guazatine [108173-90-6] + TX, dodine [2439-10-3] [1 12-65- 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 [1 17428-22-5] + 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 [801 1- 63-0] + TX, copperhydroxid [20427-59-2] + TX, copperoxychlorid [1332-40-7] + TX, coppersulfat [7758-98-7] + TX, copperoxid [1317-39-1] + TX, mancopper [53988-93-5] + TX, oxine-copper [10380-28-6] + TX, dinocap [131-72-6] + TX, nitrothal-isopropyl [10552-74-6] + TX, edifenphos [17109-49-8] + TX, iprobenphos [26087-47-8] + TX, isoprothiolane [50512-35-1] + TX, phosdiphen [36519-00-3] + TX, pyrazophos [13457-18-6] + TX, tolclofos-methyl [57018-04-9] + TX, acibenzo- lar-S-methyl [135158-54-2] + TX, anilazine [101-05-3] + TX, benthiavalicarb [413615-35-7] + TX, blasticidin-S [2079-00-7] + TX, chinomethionat [2439-01-2] + TX, chloroneb [2675-77-6] + TX, chlorothalonil [1897-45-6] + TX, cyflufenamid [180409-60-3] + TX, cymoxanil [57966-95-7] + TX, dichlone [117-80-6] + TX, diclocymet [139920-32-4] + TX, diclomezine [62865-36-5] + TX, dicloran [99-30-9] + TX, diethofencarb [87130-20-9] + TX, dimethomorph [110488-70-5] + TX, SYP-LI90 (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 [2391 10-15-7] + 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 [1 1 1 13-80-7] + 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-1 H-pyrazole-4-carboxylic acid (9-dichloromethylene-1 ,2,3,4-tetrahydro-1 ,4- methano-naphthalen-5-yl)-amide (dislosed in WO 2007/048556) + TX, 3-difluoromethyl-1-methyl-1 H- 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-e.

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-triflu^

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 [161 14-35-5] + TX, pyraziflumid [942515-63-1] + TX and 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; florylpicoxamid [1961312- 55-9] + TX; tyclopyrazoflor [1477919-27-9] + TX; pyrapropoyne [1803108-03-3] + 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 Cry1 Ab + TX, Bacillus thuringiensis aizawai GC 91 (Agree®) + TX, Bacillus thuringiensis israelensis (BMP123® + TX, Aquabac® + TX, VectoBac®) + TX, Bacillus thuringiensis kurstaki (Javelin® + TX, Deliver® + TX, CryMax® + TX, Bonide® + TX, Scutella WP® + TX, Turilav WP ® + TX, Astuto® + TX, Dipel WP® + TX, Biobit® + TX, Foray®) + TX, Bacillus thuringiensis kurstaki BMP 123 (Baritone®) + TX, Bacillus thuringiensis kurstaki HD-1 (Bioprotec-CAF / 3P®) + TX, Bacillus thuringiensis strain BD#32 + TX, Bacillus thuringiensis strain AQ52 + TX, Bacillus thuringiensis var. aizawai (XenTari® + TX, DiPel®) + TX, bacteria spp. (GROWMEND® + TX, GROWSWEET® + TX, Shootup®) + TX, bacteriophage of Clavipacter michiganensis (AgriPhage®) + TX, Bakflor® + TX, Beauveria bassiana (Beaugenic® + TX, Brocaril WP®) + TX, Beauveria bassiana GHA (Mycotrol ES® + TX, Mycotrol O® + TX, BotaniGuard®) + TX, Beauveria brongniartii (Engerlingspilz® + TX, Schweizer Beauveria® + TX, Melocont®) + TX, Beauveria spp. + TX, Botrytis cineria + TX,

Bradyrhizobium japonicum (TerraMax®) + TX, Brevibacillus brevis + TX, Bacillus thuringiensis tenebrionis (Novodor®) + TX, BtBooster + TX, Burkholderia cepacia (Deny® + TX, Intercept® + TX, Blue Circle®) + TX, Burkholderia gladii + TX, Burkholderia gladioli + TX, Burkholderia spp. + TX, Canadian thistle fungus (CBH Canadian Bioherbicide®) + TX, Candida butyri + TX, Candida famata + TX, Candida fructus + TX, Candida glabrata + TX, Candida guilliermondii + TX, Candida melibiosica + TX, Candida oleophila strain O + TX, Candida parapsilosis + TX, Candida pelliculosa + TX, Candida pulcherrima + TX, Candida reukaufii + TX, Candida saitoana (Bio-Coat® + TX, Biocure®) + TX, Candida sake + TX, Candida spp. + TX, Candida tenius + TX, Cedecea dravisae + TX, Cellulomonas flavigena + TX, Chaetomium cochliodes (Nova-Cide®) + TX, Chaetomium globosum (Nova-Cide®) + TX, Chromobacterium subtsugae strain PRAA4-1T (Grandevo®) + TX, Cladosporium cladosporioides + TX, Cladosporium oxysporum + TX, Cladosporium chlorocephalum + TX, Cladosporium spp. + TX, Cladosporium tenuissimum + TX, Clonostachys rosea (EndoFine®) + TX, Colletotrichum acutatum + TX, Coniothyrium minitans (Cotans WG®) + TX, Coniothyrium spp. + TX, Cryptococcus albidus (YIELDPLUS®) + TX, Cryptococcus humicola + TX, Cryptococcus infirmo-miniatus + TX,

Cryptococcus laurentii + TX, Cryptophlebia leucotreta granulovirus (Cryptex®) + TX, Cupriavidus campinensis + TX, Cydia pomonella granulovirus (CYD-X®) + TX, Cydia pomonella granulovirus (Madex® + TX, Madex Plus® + TX, Madex Max/ Carpovirusine®) + TX, Cylindrobasidium laeve (Stumpout®) + TX, Cylindrocladium + TX, Debaryomyces hansenii + TX, Drechslera hawaiinensis + TX, Enterobacter cloacae + TX, Enterobacteriaceae + TX, Entomophtora virulenta (Vektor®) + TX, Epicoccum nigrum + TX, Epicoccum purpurascens + TX, Epicoccum spp. + TX, Filobasidium floriforme + TX, Fusarium acuminatum + TX, Fusarium chlamydosporum + TX, Fusarium oxysporum (Fusaclean® / Biofox C®) + TX, Fusarium proliferatum + TX, Fusarium spp. + TX, Galactomyces geotrichum + TX, Gliocladium catenulatum (Primastop® + TX, Prestop®) + TX, Gliocladium roseum + TX, Gliocladium spp. (SoilGard®) + TX, Gliocladium virens (Soilgard®) + TX, Granulovirus

(Granupom®) + TX, Halobacillus halophilus + TX, Halobacillus litoralis + TX, Halobacillus trueperi + TX, Halomonas spp. + TX, Halomonas subglaciescola + TX, Halovibrio variabilis + TX, Hanseniaspora uvarum + TX, Helicoverpa armigera nucleopolyhedrovirus (Helicovex®) + TX, Helicoverpa zea nuclear polyhedrosis virus (Gemstar®) + TX, Isoflavone - formononetin (Myconate®) + TX, Kloeckera apiculata + TX, Kloeckera spp. + TX, Lagenidium giganteum (Laginex®) + TX, Lecanicillium longisporum (Vertiblast®) + TX, Lecanicillium muscarium (Vertikil®) + TX, Lymantria Dispar nucleopolyhedrosis virus (Disparvirus®) + TX, Marinococcus halophilus + TX, Meira geulakonigii + TX, Metarhizium anisopliae (Met52®) + TX, Metarhizium anisopliae (Destruxin WP®) + TX, Metschnikowia fruticola (Shemer®) + TX, Metschnikowia pulcherrima + TX, Microdochium dimerum (Antibot®) + TX, Micromonospora coerulea + TX, Microsphaeropsis ochracea + TX, Muscodor albus 620 (Muscudor®) + TX, Muscodor roseus strain A3-5 + TX, Mycorrhizae spp. (AMykor® + TX, Root Maximizer®) + TX, Myrothecium verrucaria strain AARC-0255 (DiTera®) + TX, BROS PLUS® + TX, Ophiostoma piliferum strain D97 (Sylvanex®) + TX, Paecilomyces farinosus + TX, Paecilomyces fumosoroseus (PFR-97® + TX, PreFeRal®) + TX, Paecilomyces linacinus (Biostat WP®) + TX, Paecilomyces lilacinus strain 251 (MeloCon WG®) + TX, Paenibacillus polymyxa + TX, Pantoea agglomerans (BlightBan C9-1®) + TX, Pantoea spp. + TX, Pasteuria spp. (Econem®) + TX, Pasteuria nishizawae + TX, Penicillium aurantiogriseum + TX, Penicillium billai (Jumpstart® + TX, TagTeam®) + TX, Penicillium

brevicompactum + TX, Penicillium frequentans + TX, Penicillium griseofulvum + TX, Penicillium purpurogenum + TX, Penicillium spp. + TX, Penicillium viridicatum + TX, Phlebiopsis gigantean

(Rotstop®) + TX, phosphate solubilizing bacteria (Phosphomeal®) + TX, Phytophthora cryptogea + TX, Phytophthora palmivora (Devine®) + TX, Pichia anomala + TX, Pichia guilermondii + TX, Pichia membranaefaciens + TX, Pichia onychis + TX, Pichia stipites + TX, Pseudomonas aeruginosa + TX, Pseudomonas aureofasciens (Spot-Less Biofungicide®) + TX, Pseudomonas cepacia + TX,

Pseudomonas chlororaphis (AtEze®) + TX, Pseudomonas corrugate + TX, Pseudomonas fluorescens strain A506 (BlightBan A506®) + TX, Pseudomonas putida + TX, Pseudomonas reactans + TX, Pseudomonas spp. + TX, Pseudomonas syringae (Bio-Save®) + TX, Pseudomonas viridiflava + TX, Pseudomons fluorescens (Zequanox®) + TX, Pseudozyma flocculosa strain PF-A22 UL (Sporodex L®) + TX, Puccinia canaliculata + TX, Puccinia thlaspeos (Wood Warrior®) + TX, Pythium

paroecandrum + TX, Pythium oligandrum (Polygandron® + TX, Polyversum®) + TX, Pythium periplocum + TX, Rhanella aquatilis + TX, Rhanella spp. + TX, Rhizobia (Dormal® + TX, Vault®) + TX, Rhizoctonia + TX, Rhodococcus globerulus strain AQ719 + TX, Rhodosporidium diobovatum + TX, Rhodosporidium toruloides + TX, Rhodotorula spp. + TX, Rhodotorula glutinis + TX, Rhodotorula graminis + TX, Rhodotorula mucilagnosa + TX, Rhodotorula rubra + TX, Saccharomyces cerevisiae + TX, Salinococcus roseus + TX, Sclerotinia minor + TX, Sclerotinia minor (SARRITOR®) + TX,

Scytalidium spp. + TX, Scytalidium uredinicola + TX, Spodoptera exigua nuclear polyhedrosis virus (Spod-X® + TX, Spexit®) + TX, Serratia marcescens + TX, Serratia plymuthica + TX, Serratia spp. + TX, Sordaria fimicola + TX, Spodoptera littoralis nucleopolyhedrovirus (Littovir®) + TX,

Sporobolomyces roseus + TX, Stenotrophomonas maltophilia + TX, Streptomyces ahygroscopicus + TX, Streptomyces albaduncus + TX, Streptomyces exfoliates + TX, Streptomyces galbus + TX, Streptomyces griseoplanus + TX, Streptomyces griseoviridis (Mycostop®) + TX, Streptomyces lydicus (Actinovate®) + TX, Streptomyces lydicus WYEC-108 (ActinoGrow®) + TX, Streptomyces violaceus + TX, Tilletiopsis minor + TX, Tilletiopsis spp. + TX, Trichoderma asperellum (T34 Biocontrol®) + TX, Trichoderma gamsii (Tenet®) + TX, Trichoderma atroviride (Plantmate®) + TX, Trichoderma hamatum TH 382 + TX, Trichoderma harzianum rifai (Mycostar®) + TX, Trichoderma harzianum T-22 (Trianum- P® + TX, PlantShield HC® + TX, RootShield® + TX, Trianum-G®) + TX, Trichoderma harzianum T-39 (Trichodex®) + TX, Trichoderma inhamatum + TX, Trichoderma koningii + TX, Trichoderma spp. LC 52 (Sentinel®) + TX, Trichoderma lignorum + TX, Trichoderma longibrachiatum + TX, Trichoderma polysporum (Binab T®) + TX, Trichoderma taxi + TX, Trichoderma virens + TX, Trichoderma virens (formerly Gliocladium virens GL-21 ) (SoilGuard®) + TX, Trichoderma viride + TX, Trichoderma viride strain ICC 080 (Remedier®) + TX, Trichosporon pullulans + TX, Trichosporon spp. + TX,

Trichothecium spp. + TX, Trichothecium roseum + TX, Typhula phacorrhiza strain 94670 + TX, Typhula phacorrhiza strain 94671 + TX, Ulocladium atrum + TX, Ulocladium oudemansii (Botry-Zen®) + TX, Ustilago maydis + TX, various bacteria and supplementary micronutrients (Natural II®) + TX, various fungi (Millennium Microbes®) + TX, Verticillium chlamydosporium + TX, Verticillium lecanii (Mycotal® + TX, Vertalec®) + TX, Vip3Aa20 (VIPtera®) + TX, Virgibaclillus marismortui + TX, Xanthomonas campestris pv. Poae (Camperico®) + TX, Xenorhabdus bovienii + TX, Xenorhabdus nematophilus; and

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

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 + ΤΧ,Ζ + ΤΧ,Ζ)- 3 + TX,8 + TX,1 1 Tetradecatrienyl acetate + TX, (Z + ΤΧ,Ζ + TX,E)-7 + TX, 1 1 + 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, Steinemema carpocapsae (Nematac C® + TX, Millenium® + TX, BioNem C® + TX, NemAttack® + TX, Nemastar® + TX, Capsanem®) + TX, Steinemema feltiae (NemaShield® + TX, Nemasys F® + TX, BioNem F® + TX, Steinernema-System® + TX, NemAttack® + TX, Nemaplus® + TX, Exhibitline sf® + TX, Scia-rid® + TX, Entonem®) + TX, Steinemema kraussei (Nemasys L® + TX, BioNem L® + TX, Exhibitline srb®) + TX, Steinemema riobrave (BioVector® + TX, BioVektor®) + TX, Steinemema scapterisci (Nematac S®) + TX, Steinemema 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

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.

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.

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 lUPAC name, the lUPAC/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.

The active ingredient mixture of the compounds of formula I selected from Tables 1 to 12 and P1 with active ingredients described above comprises a compound selected from Tables 1 to 12 and P1 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.

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.

The mixtures comprising a compound of formula I selected from Tables 1 to 12 and P1 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 1 to 12 and P1 and the active ingredients as described above is not essential for working the present invention.

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.

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. 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.

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. 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. 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.

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).

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:

Example B1 : Activity against Spodoptera littoralis (Egyptian cotton leaf worm)

Cotton leaf discs were placed on agar in 24-well microtiter plates and sprayed with agueous test solutions prepared from 10Ό00 ppm DMSO stock solutions. After drying the leaf discs were infested with five L1 larvae. The samples were assessed for mortality, anti-feedant effect, and growth inhibition in comparison to untreated samples 3 days after infestation. Control of Spodoptera littoralis by a test sample is when at least one of mortality, anti-feedant effect, and growth inhibition is higher than the untreated sample. The following compounds resulted in at least 80% control at an application rate of 200 ppm: P5 and

Example B2: Activity against Spodoptera littoralis (Egyptian cotton leaf worm)

Test compounds were applied by pipette from 10Ό00 ppm DMSO stock solutions into 24-well plates and mixed with agar. Lettuce seeds were placed on the agar and the multi well plate was closed by another plate which contains also agar. After 7 days the roots have absorbed the compound and the lettuce has grown into the lid plate. The lettuce leafs were now cut off into the lid plate. Spodoptera eggs were pipetted through a plastic stencil on a humid gel blotting paper and the plate closed with it. The samples were assessed for mortality, anti-feedant effect and growth inhibition in comparison to untreated samples 6 days after infestation.

The following compound gave an effect of at least 80% in at least one of the three categories (mortality, anti-feedancy, or growth inhibition) at a test rate of 12.5 ppm: P8. Example B3: Activity against Plutella xylostella (Diamond back moth)

24-well microtiter plates with artificial diet were treated with agueous test solutions prepared from 10Ό00 ppm DMSO stock solutions by pipetting. After drying, the plates were infested with L2 larvae (10 to 15 per well). The samples were assessed for mortality and growth inhibition in comparison to untreated samples 5 days after infestation.

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: P5 and P8.

Example B4: Activity against Diabrotica balteata (Corn root worm)

Maize sprouts, placed on an agar layer in 24-well microtiter plates were treated with agueous test solutions prepared from 10Ό00 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.

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: P5 and P8. Example B5: Activity against Myzus persicae (Green peach aphid)

Sunflower leaf discs were placed on agar in a 24-well microtiter plate and sprayed with agueous test solutions prepared from 10Ό00 ppm DMSO stock solutions. After drying, the leaf discs were infested with an aphid population of mixed ages. The samples were assessed for mortality 6 days after infestation.

The following compounds resulted in at least 80% mortality at an application rate of 200 ppm: P5 and P8.

Example B6: Activity against Myzus persicae (Green peach aphid) Roots of pea seedlings infested with an aphid population of mixed ages were placed directly in the aqueous test solutions prepared from 10Ό00 DMSO stock solutions. The samples were assessed for mortality 6 days after placing seedlings in test solutions.

The following compounds resulted in at least 80% mortality at a test rate of 24 ppm: P5, P6 and P8. Example B7: Activity against Myzus persicae (Green peach aphid)

Test compounds from 10Ό00 ppm DMSO stock solutions were applied by pipette into 24-well microtiter plates and mixed with sucrose solution. The plates were closed with a stretched Parafilm. A plastic stencil with 24 holes was placed onto the plate and infested pea seedlings were placed directly on the Parafilm. The infested plate was closed with a gel blotting paper and another plastic stencil and then turned upside down. The samples were assessed for mortality 5 days after infestation.

The following compounds resulted in at least 80% mortality at a test rate of 12 ppm: P6.

Example B8: Activity against Bemisia tabaci (Cotton white fly)

Cotton leaf discs were placed on agar in 24-well microtiter plates and sprayed with agueous test solutions prepared from 10Ό00 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 compound resulted in at least 80% mortality at an application rate of 200 ppm: P8.

Example B9: Activity against Euschistus ?eros(Neotropical Brown Stink Bug)

Soybean leaf on agar in 24-well microtiter plates were sprayed with agueous test solutions prepared from 10Ό00 ppm DMSO stock solutions. After drying the leaf were infested with N-2 nymphs. The samples were assessed for mortality and growth inhibition in comparison to untreated samples 5 days after infestation.

The following compounds gave an effect of at least 80% in at least one of the two categories (mortality or growth inhibition) at an application rate of 200 ppm: P8.

Claims

Claims:

1. A compound of formula I

wherein

Gi is nitrogen or CF¾;

G2 is a five- to six-membered, aromatic, partially saturated or fully saturated ring system linked via a nitrogen atom to the imidazole or triazole ring which contains the group Gi , said ring system can be mono- or polysubstituted by substituents selected from the group consisting of halogen, cyano, Ci-C4alkyl, Ci-C4haloalkyl, Ci-C4haloalkoxy, Ci-C4alkoxy, Ci-C4alkylsulfanyl, Ci-C4alkylsulfinyl, Ci-C4alkylsulfonyl, -C(0)Ci-C4alkyl, Ci-C4haloalkylsulfanyl, Ci-C4haloalkylsulfinyl,

G2 is a five-membered, aromatic, partially saturated or fully saturated ring system linked via a carbon atom to the imidazole or triazole ring which contains the group Gi , said ring system can be mono- or polysubstituted by substituents selected from the group consisting of halogen, cyano, Ci-C4alkyl, Ci-C4haloalkyl, Ci-C4haloalkoxy, Ci-C4alkoxy, Ci-C4alkylsulfanyl, Ci-C4alkylsulfinyl, Ci-C4alkylsulfonyl, -C(0)Ci-C4alkyl, Ci-C4haloalkylsulfanyl, Ci-C4haloalkylsulfinyl, Ci-C4haloalkylsulfonyl and

-C(0)Ci-C4haloalkyl; and said ring system can contain 1 , 2 or 3 heteroatoms selected from the group consisting of nitrogen, oxygen and sulfur, where said ring system may not contain more than one oxygen atom and not more than one sulfur atom; or

G2 is a six-membered, partially saturated or fully saturated ring system linked via a carbon atom to the imidazole or triazole ring which contains the group Gi , said ring system can be mono- or

polysubstituted by substituents selected from the group consisting of halogen, cyano, Ci-C4alkyl,

-C(0)Ci-C4haloalkyl; and said ring system can contain 1 , 2 or 3 heteroatoms selected from the group consisting of nitrogen, oxygen and sulfur, where said ring system may not contain more than one oxygen atom and not more than one sulfur atom;

Re is hydrogen, Ci-C4alkyl or Ci-C4haloalkyl;

R9 is hydrogen, Ci-C4alkyl, Ci-C4haloalkyl, cyano or halogen;

R7 is a radical selected from the group consisting of formula Qi and Q2

Qi Q2

and wherein A represents CH or N;

Q is hydrogen, halogen, Ci-C6haloalkoxy or Ci-C6haloalkyl; or

polysubstituted by substituents selected from the group consisting of halogen, cyano, Ci-C4alkyl, Ci- C4haloalkyl, Ci-C4haloalkoxy, Ci-C4alkoxy, Ci-C4alkylsulfanyl, Ci-C4alkylsulfinyl, Ci-C4alkylsulfonyl, -C(0)Ci-C₄alkyl, Ci-C₄haloalkylsulfanyl, Ci-C₄haloalkylsulfinyl, Ci-C₄haloalkylsulfonyl and

-C(0)Ci-C4haloalkyl; and said ring system contains 1 , 2 or 3 heteroatoms selected from the group consisting of nitrogen, oxygen and sulfur, where said ring system may not contain more than one oxygen atom and not more than one sulfur atom; or

Q is C2-C6alkenyl, or C2-C6alkenyl mono- or polysubstituted by substituents selected from the group consisting of halogen, cyano, Ci-C4alkyl, Ci-C4haloalkyl, C3-C6cycloalkyl and phenyl, wherein said phenyl can be mono- or polysubstituted by substituents selected from the group consisting of halogen, cyano, Ci-C4alkyl, Ci-C4haloalkyl, Ci-C4haloalkoxy, Ci-C4alkoxy, Ci-C4haloalkylsulfanyl, Ci-C4halo- alkylsulfinyl, Ci-C4haloalkylsulfonyl and -C(0)Ci-C4haloalkyl; or Q is C2-C6alkynyl, or C2-C6alkynyl mono- or polysubstituted by substituents selected from the group consisting of halogen, cyano, Ci-C4alkyl, Ci-C4haloalkyl, C3-C6cycloalkyl, tri(Ci-C4alkyl)silyl and phenyl, wherein said phenyl can be mono- or polysubstituted by substituents selected from the group consisting of halogen, cyano, Ci-C4alkyl, Ci-C4haloalkyl, Ci-C4haloalkoxy, Ci-C4alkoxy, Ci-C4halo- alkylsulfanyl, Ci-C4haloalkylsulfinyl, Ci-C4haloalkylsulfonyl and -C(0)Ci-C4haloalkyl; or

X is S, SO or S0₂; and

Ri is C2-C6alkenyl, C2-C6haloalkenyl or C2-C6alkynyl; and

with the proviso that when Gi is CR9, then the ring system G2 is not aromatic;

and agrochemically acceptable salts, stereoismers, enantiomers, tautomers and N-oxides of the compounds of formula I.

2. A compound of formula I according to claim 1 , wherein

Q is selected from hydrogen, halogen, Ci-C6haloalkoxy, Ci-C6haloalkyl, Ci-C6haloalkylsulfanyl, Ci-C6haloalkylsulfinyl, Ci-C6haloalkylsulfonyl, -C(0)Ci-C4haloalkyl, and from the group consisting of J-0 to J-48:

J-0 J-1 J-2 J-3 J-4 J-5

J-6 J-7 J-8 J-9 J-10 J-11

J-12 J-13 J-14 J-15 J-16

J-17 J-18 J-19 J-20 J-21 J-22

J-23 J-24 J-25 J-26 J-27 J-28

wherein each group J-0 to J-48 is mono-, di- or trisubstituted with Rx, wherein

3. A compound of formula I according to claim 1 , wherein

G2 is selected from the rou consistin of G-0 to G-37:

G-16 G-17

G-36 G-37

wherein each group G-0 to G-37 is mono-, di- or trisubstituted with Rx, wherein

each Rx is, independently selected from the group consisting of hydrogen, halogen, cyano, Ci-C4alkyl,

Ci-C4haloalkyl, Ci-C4haloalkoxy, Ci-C4alkoxy, Ci-C4alkylsulfanyl, Ci-C4alkylsulfinyl, Ci-C4alkylsulfonyl,

-C(0)Ci-C₄alkyl, Ci-C₄haloalkylsulfanyl, Ci-C₄haloalkylsulfinyl, Ci-C₄haloalkylsulfonyl and -C(0)Ci-

C4haloalkyl.

4. A compound of formula I according to claim 1 , represented by the compounds of formula 1-1

wherein

A is as defined under formula I in claim 1 ;

Qai is Q as defined under formula I in claim 1 ;

G2-1 is G2 as defined under formula I in claim 1 ;

R11 is methyl, ethyl, n-propyl, i-propyl or cyclopropylmethyl;

Re is as defined above under formula I in claim 1 ; and

G11 is N or CR9, wherein R9 is as defined above under formula I in claim 1.

5. A compound of formula 1-1 according to claim 4, wherein

G2-1 is selected from the group consisting of

Q-A G-28 G-29 G-31 Τ G-32 G-36

6. A compound of formula I according to claim 1 represented by the compounds of formula I-2

wherein

A is as defined under formula I in claim 1 ;

G2-2 is G2 as defined under formula I in claim 1 ;

X₂ is S, SO or S0₂;

R12 is methyl, ethyl, n-propyl, i-propyl or cyclopropylmethyl;

Re is as defined above under formula I in claim 1 ;

G12 is N or CR9, wherein R9 is as defined above under formula I in claim 1 ; and

Qa∑ is selected from hydrogen, halogen, Ci-C6haloalkoxy, Ci-C6haloalkyl, Ci-C6haloalkyl-sulfanyl, Ci-C6haloalkylsulfinyl, Ci-C6haloalkylsulfonyl, -C(0)Ci-C4haloalkyl, and from the group consisting of J-0 to J-48:

J-0 J-1 J-2 J-3 J-4 J-5

J-6 J-7 J-8 J-10 J-11

J-17 J-18 J-19 J-20 J-21 J-22

J-23 J-27 J-28

J-29 J-33 J-34

wherein each group J-0 to J-48 is mono-, di- or trisubstituted with Rx, wherein

7. A compound of formula 1-1 according to claim 6, wherein

Qa∑ is Ci-C6haloalkyl.

8. A compound of formula I according to claim 1 represented by the compounds of formula I-3

wherein

A is N or CH;

Gi3 is N or CR9, wherein R9 is as defined above under formula I in claim 1 ;

G2-3 is selected from the group consistin of

wherein each group G is mono-, di- or trisubstituted with Rx, wherein each Rx is, independently selected from the group consisting of hydrogen, Ci-C4alkyl and Ci-C4haloalkyl;

X₃ is S, SO or S0₂;

Qa3 is selected from the group consisting of Ci-C6haloalkyl;

Ri3 is Ci-C4alkyl; and

Rs is Ci-C₄alkyl.

9. A compound of formula I according to claim 1 represented by the compounds of formula I-4

wherein

A is N;

G2-4 is selected from the group consisting of

wherein each Rx is, independently selected from the group consisting of hydrogen, Ci-C4alkyl and Ci- C4haloalkyl; and

Qa4 is selected from the group consisting of Ci-C6haloalkyl.

10. A compound of formula Ilia

wherein

Re and R7 are as defined under formula I in claim 1 ;

LG is iodine or bromine.

1 1 . A compound of formula IVa

wherein

Re and R7 are as defined under formula I in claim 1 ; and

d is N or CH.

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

13. A method for controlling pests, which comprises applying a composition according to claim 10 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.

14. A method for the protection of plant propagation material from the attack by pests, which comprises treating the propagation material or the site, where the propagation material is planted, with a composition according to claim 12.