WO2019175712A1 - Nouvelles utilisations de molécules de catéchol en tant qu'inhibiteurs de voies métaboliques de glutathion s-transférase - Google Patents

Nouvelles utilisations de molécules de catéchol en tant qu'inhibiteurs de voies métaboliques de glutathion s-transférase Download PDF

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WO2019175712A1
WO2019175712A1 PCT/IB2019/051801 IB2019051801W WO2019175712A1 WO 2019175712 A1 WO2019175712 A1 WO 2019175712A1 IB 2019051801 W IB2019051801 W IB 2019051801W WO 2019175712 A1 WO2019175712 A1 WO 2019175712A1
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methyl
alkyl
chloro
phenyl
aryl
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PCT/IB2019/051801
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English (en)
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Tony Durst
John Thor Arnason
Suqi LIU
Hector AREVALO
Michael David
Ramakrishnan VALLINAYAGAM
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Basf Corporation
University Of Ottawa
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
    • C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
    • C07D317/50—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to atoms of the carbocyclic ring
    • C07D317/54—Radicals substituted by oxygen atoms
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
    • A01N43/24—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms
    • A01N43/26—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms five-membered rings
    • A01N43/28—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms five-membered rings with two hetero atoms in positions 1,3
    • A01N43/30—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms five-membered rings with two hetero atoms in positions 1,3 with two oxygen atoms in positions 1,3, condensed with a carbocyclic ring
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
    • C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
    • C07D317/62—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to atoms of the carbocyclic ring
    • C07D317/64—Oxygen atoms

Definitions

  • the present invention relates to a use of compounds of the formula (I) as Glutathione-S- transferase inhibitor.
  • the invention further relates to a method of controlling crop pests and/or non-crop pests that are resistant to one or more insecticide(s) and method of controlling undesired vegetation that are resistant to one or more herbicide(s) by applying at least one glutathione S-transferase (GST) inhibitor of formula (I).
  • GST glutathione S-transferase
  • Glutathione-S-transferases form a large enzyme family ubiquitously expressed in animals and plants. GSTs are involved in the cellular defense against a broad spectrum of cytotoxic agents (Gate and Tew, 2001 ). Up until today, over 400 different GST sequences have been identified. Based on their genetic characteristics and substrate specificity, the various GSTs can be classified in at least four different classes a, m, p and Q (Mannervik et al.,
  • the World Health Organization has defined resistance as“the development of an ability in a strain of insects to tolerate dose of toxicant that would prove lethal to the majority of individuals in a normal population of the same species”.
  • IRAC Insecticide Resistance Action Committee
  • resistance may be defined as‘a heritable change in the sensitivity of a pest population that is reflected in the repeated failure of a product to achieve the expected level of control when used according to the label recommendation for that pest species’ (www.irac- online.org).
  • Cross-resistance occurs when resistance to one insecticide confers resistance to another insecticide, even where the insect has not been exposed to the latter product.
  • Pesticide resistance and herbicide resistance is therefore to be similarly construed.
  • the resistance may be partial or complete and it will be appreciated that all degrees of resistance are included in the meaning of this term, whether they be very low resistance, low resistance, high resistance, very high resistance or total resistance.
  • Natural selection by a pesticide allows some naturally occurring, pre-adapted pests with re sistance genes to survive and to pass-on the resistance trait to their offspring. Through continued application of pesticides with the same MoA, selection for the resistant individuals persists so the proportion of resistant pests in the population increases, while susceptible individuals are eliminated by the pesticide. Under this permanent selection pressure, resistant pests outnumber susceptible ones and the pesticide is no longer effective. The speed with which resistance develops depends on several factors, including how fast the pests
  • the insecticide resistant insects can detoxify by destruction or excretion in comparison to normal non-resistant insects, e.g. due to their metabolism such as their enzyme systems. Metabolic resistance is very often dependent on the structure of the active ingredient. Therefore, the metabolic resistance is most likely overcome by actives with a different chemical structure.
  • Another resistance mechanism is a modification of the target structure (protein, receptor, ion channel, etc.) of the insecticide. The insecticidal activity is reduced by a change in the binding site, e.g. due to point mutations, which are passed on. Further, there is also resistance due to behavioral change and penetration resistance (the outer shell of the insect developed barriers that slow down the penetration of insecticides in the body of the insect). In resistant pests, a combination of several of these resistance mechanisms can be found.
  • a resistance mechanism that is responsible for the resistance of a pest to a particular insecticide these pests also faces a new insecticide resistant making (cross-) resistance, is difficult because of the different resistance mechanisms before-seen. Particularly in cases where the mechanism of action of the new insecticide or is not known, or where the resistance by mechanisms other than by changing the binding site, for example by metabolic resistance is mediated, the prediction of a cross-resistance is difficult.
  • Piperonyl butoxide is a compound that was discovered in the 1950’s as a synergist for pyrethroid type insecticides.
  • PBO acts as an insecticide synergist by inhibiting the natural defense mechanisms of the insect, the most important of which is the mixed-function oxidase system, (MFOs) also known as the cytochrome P450 system.
  • MFOs mixed-function oxidase system
  • the MFO system is the primary route of detoxification in insects, and causes the oxidative breakdown of insecticides such as pyrethrins and the synthetic pyrethroids. It’s effect on GST pathway is very limited (Casida, J. E. (1970). MFO involvement in the biochemistry of insecticide synergists. J. Agric. Food Chem. 18, 753-772).
  • IRM Insecticide Resistance Management
  • IPM integrated pest management
  • Insects have several pathways to metabolize exogenous molecules that they are exposed to. These molecular transformations can either activate an insecticide, such is the case of pro drugs. Alternatively, these mechanisms can also confer the insect what is known as metabolic resistance. In this instance, the metabolism of the insect transforms the insecticide molecules in such way they are deactivated and become harmless to the insects and easily excretable.
  • Esterases Catalyze the hydrolysis of ester-insecticides into their respective acid and alcohol compounds. This process increases the polarity of the compounds making them easier to excrete. Esterases can also sequester some insecticides in such way that they are not available for interaction with the insect proteins making them non-toxic to the insect.
  • One of the most known examples is the insecticide detoxification by the overproduction of a specific
  • Glutathione S-transferases (GST). Insect GSTs are divided into two different groups
  • the GST pathway catalyzes the conjugation of the reduced form of glutathione to xenobiotic substrates for the purpose of detoxification and then easy excretion.
  • DDT deactivation by DDT- dehydrochlorinase GST which also has been reported as being responsible for DDT resistance in houseflies and mosquitoes (Enayati et al., 2005).
  • Puinean AM Foster SP, Oliphant L, Denholm I, Field LM, Millar NS et al.
  • Amplification of a cytochrome P450 gene is associated with resistance to neonicotinoid insecticides in the aphid Myzus persicae. PLOS Genet 6:e1000999, 2010.
  • WO 2012/123714 provides composition and methods for controlling pests which show resistance to neonicotinoid by using compositions comprising neonicotinoid and a neonicotinoid synergist.
  • It an object of the presently claimed invention to provide new uses, methods and compositions for controlling these pesticide, both crop and non-crop pests, resistant and herbicide resistant induced diseases in crops. It is another object of the presently claimed invention to provide a method for controlling pests, including crop and/or non-crop, which are resistant to one or more classes of insecticides, in particular cyclodienes, organophosphates, carbamates,
  • the present invention fulfils the need in the art and moreover provides the additional related advantages.
  • the present invention is based on the surprising finding that compounds of the formula (I) are capable of binding to GSTs with high affinity and, hence, act as GST inhibitor.
  • the present invention relates to the use of a compound of formula
  • R 2 is OR 7 or N R 8 R 9 , wherein
  • R 7 is H, Ci-Ci 2 -alkyl, C 2 -Ci 2 -alkenyl, C 2 -Ci 2 -alkynyl, (CR 5 R 6 ) n C 5 -Ci 4 -aryl, (CR 5 R 6 ) respectfulC 5 -Ci 4 - heteroaryl, (CR 5 R 6 ) n C 3 -Ci 2 -cycloalkyl, (CR 5 R 6 ) n C 5 -Ci 4 -aryl- C 3 -Ci 2 -membered heterocycloalkyl, (CR 5 R 6 )nC 5 -Ci 2 -membered heterocycloalkyl or (CR 5 R 6 ) n C 5 -Ci 4 -membered heterocycloalkenyl; whereby R 7 is unsubstituted or further substituted by 1 , 2, 3, 4 or 5 identical or different groups R 12b which are independently selected from F, Cl, Br, I , OH
  • R 3 is Ci-Ci2-alkyl, C 2 -Ci 2 -alkenyl, C 2 -Ci2-alkynyl, (CR 5 R 6 ) n C5-Ci4-aryl, (CR 5 R 6 ) n C 5 -Ci 4 - heteroaryl, (CR 5 R 6 ) n C3-Ci 2 -cycloalkyl, (CR 5 R 6 ) n C3-Ci 2 -heterocycloalkyl or (CR 5 R B ) n C3-Ci2- heterocycloalkenyl;
  • R 10 and R 11 are H, OrC ⁇ -cycloalkyl, C 2 -C 12-alkenyl, C 2 -Ci 2 -alkynyl or Cr C12 alkyl or R 10 together with R 11 forms Cs-Cn-membered heterocycloalkyl, Cs-Ci4-membered heterocycloalkenyl or C 5 -Ci4-membered heteroaryl;
  • R 12 and R 13 are H, C3-Ci 2 -cycloalkyl, C 2 -C 12-alkenyl, C 2 -Ci 2 -alkynyl or Ci- C12 alkyl or R 12 together with R 13 forms C 5 -Ci 4 -membered heterocycloalkyl, C 5 -Ci 4 -membered heterocycloalkenyl or Cs-Cn-membered heteroaryl;
  • substituents those substituents may be the same or different.
  • Ci-Ci 2 -alkyl refers to a straight-chained or branched saturated hydrocarbon group having 1 to 12 carbon atoms, for example, methyl, ethyl, propyl, 1-methylethyl, butyl, 1- methylpropyl, 2-methylpropyl, 1 ,1 -dimethylethyl, pentyl, 1 -methylbutyl, 2-methylbutyl, 3- methylbutyl, 2,2-dimethylpropyl, 1 -ethyl propyl, 1 ,1-dimethylpropyl, 1 ,2-dimethylpropyl, hexyl, 1- methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1 ,1 -dimethylbutyl, 1 ,2- dimethylbutyl, 1 ,3-dim ethyl butyl, 2, 2-dim ethyl butyl, 2,3-
  • C 2 -Ci2-alkenyl refers to a straight-chain or branched unsaturated hydrocarbon radical having 2 to 6 carbon atoms and a double bond in any position.
  • Examples are "C 2 -C 4 - alkenyl” groups, such as ethenyl, 1 -propenyl, 2-propenyl, 1-methylethenyl, 1 -butenyl, 2-butenyl, 3-butenyl, 1 -methyl-1 -propenyl, 2-methyl-1 -propenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl.
  • C 2 -Ci 2 -alkynyl refers to a straight-chain or branched unsaturated hydrocarbon radical having 2 to 6 carbon atoms and containing at least one triple bond.
  • Examples are "C 2 -C 4 alkynyl” groups, such as ethynyl, prop-1-ynyl, prop-2-ynyl, but-1-ynyl, but-2-ynyl, but-3-ynyl, 1- methyl-prop-2-ynyl.
  • C3-Ci 2 -cycloalkyl refers to monocyclic saturated hydrocarbon radicals having 3 to 8 carbon ring members, such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl or cyclooctyl.
  • C5-Ci 4 -aryl refers to aromatic radicals, for example Cs-C 6 -aryl radicals, for example phenyl or cyclopenta-1 , 3-diene.
  • C5-Ci 4 -heteroaryl means an aryl group where at least one carbon atom on the hydrocarbon chain normally carrying 5 to 14 carbon atoms is substituted by another atom selected from N, O, oxo or S, for example, pyridyl, pyridinone, pyrimidyl, pyrazinyl, pyridazinyl, triazinyl, thienyl, furanyl, pyrrolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, imidazolyl, triazolyl, thiadiazolyl, oxadiazolyl and tetrazolyl rings. Any monocyclic which has the characteristics of aromaticity in terms of electron distribution throughout the ring system is included in this definition.
  • C 5 -Ci4-membered heterocycloalkenyl refers to 5 to 14 membered monocyclic ring system having one or more heteroatoms, such as O, N, oxo, S as ring members and one or more double bonds.
  • C 5 -C 6 -heterocycloalkenyl refers to a cyclic unsaturated hydrocarbon residue with 5 or 6 carbon atoms, which comprises at least one double bond, and wherein, one or more C atoms are replaced by heteroatoms independently selected from O, N, oxo or S, for example, (2,3)-dihydrofuranyl, (2,3)-dihydrothienyl, (2,3)- dihydropyrrolyl, (2,5)-dihydropyrrolyl, (2,5)-dihydropyrrolyl, (2,3)-dihydroisoxazolyl, (1 ,4)- dihydropyridin-1-yl, dihydropyranyl, 2,3-dihydropyrazol-1 -yl, 2,3-dihydropyrazol-2-yl, 2,3- dihydropyrazol-3-yl, 2,3-dihydropyrazoW-yl, 2,3-dihydr
  • Cs-Cu-membered heterocycloalkyl means a non-aromatic monocyclic or polycyclic ring comprising 5 to 14 carbon atoms and at least one heteroatom selected from O, S, oxo and N.
  • a heterocycloalkyl group can have one or more carbon-carbon double bonds or carbon- heteroatoms double bonds in the ring as long as the ring is not rendered aromatic by their presence.
  • heterocycloalkyl groups include aziridinyl, pyrrolidinyl, pyrrolidino, piperidinyl, piperidino, piperazinyl, piperazino, morpholinyl, morpholino, thiomorpholinyl, thiomorpholino, tetrahydrofuranyl, tetrahydrothiofuranyl, tetrahydropyranyl and pyranyl.
  • the present invention relates to the use of compound of formula (I) as GST inhibitor, wherein
  • R 1 and R 4 are selected from the group consisting of H, F, Cl, Br and I;
  • the present invention relates to the use of compound of formula (I) as GST inhibitor, wherein R 1 and R 4 , identical or different, are selected from the group consisting of H, F, Cl and Br.
  • the present invention relates to the use of compound of formula (I) as GST inhibitor, wherein the compound of formula (I) is:
  • the present invention relates to the method to elucidate the mechanism of resistance in a strain of insects, via application of glutathione S-transferase (GST) inhibitor of formula (I), along with the insecticide to which the strain shows resistance, whereupon antagonism of resistance would implicate native GST enzymes in the resistance mechanism of said strain.
  • GST glutathione S-transferase
  • the present invention provides the method to guide synthetic optimization of novel insecticides, where co-application of experimental insecticide with glutathione S-transferase (GST) inhibitor of formula (I) to pest insect strains could inform design of new insecticide structures more likely to circumvent metabolic detoxification by pest insects.
  • GST glutathione S-transferase
  • the compounds according to the present invention may be provided as mixtures with at least one mixing partner such as an insecticide, herbicide or biopesticide, or as compositions comprising an auxiliary and at least one compound of the present invention or a mixture thereof. Suitable formulations will be described further below.
  • the compound of the formula (I) may have one or more centres of chirality, in which case they are present as mixtures of enantiomers or diastereomers.
  • the invention provides both the pure enantiomers or pure diastereomers of the compounds of formula (I), and their mixtures and the use according to the invention of the pure enantiomers or pure diastereomers of the compound of formula (I) or its mixtures.
  • Suitable compounds of the formula (I) also include all possible geometrical stereoisomers (cis/trans isomers) and mixtures thereof. Cis/trans isomers may be present with respect to an alkene, carbon-nitrogen double-bond, nitrogen-sulfur double bond or amide group.
  • stereoisomer(s) encompasses both optical isomers, such as enantiomers or diastereomers, the latter existing due to more than one centre of chirality in the molecule, as well as geometrical isomers (cis/trans isomers).
  • tautomer refers to the coexistence of two (or more) compounds that differ from each other only in the position of one (or more) mobile atoms and in electron distribution, for example, keto-enol tautomers.
  • Salts of the compounds of the present invention are preferably agriculturally and veterinarily acceptable salts. They can be formed in a customary method, e.g. by reacting the compound with an acid if the compound of the present invention has a basic functionality or by reacting the compound with a suitable base if the compound of the present invention has an acidic functionality.
  • suitable“agriculturally useful salts” or“agriculturally acceptable salts” are especially the salts of those cations or the acid addition salts of those acids whose cations and anions, respectively, do not have any adverse effect on the action of the compounds according to the present invention.
  • Suitable cations are in particular the ions of the alkali metals, preferably lithium, sodium and potassium, of the alkaline earth metals, preferably calcium, magnesium and barium, and of the transition metals, preferably manganese, copper, zinc and iron, and also ammonium (NH 4 + ) and substituted ammonium in which one to four of the hydrogen atoms are replaced by Ci-C 4 -alkyl, Ci-C -hydroxyalkyl, Ci-C 4 -alkoxy, Ci-C 4 -alkoxy-Ci-C 4 -alkyl, hydroxy-Cr C 4 -alkoxy-Ci-C 4 -alkyl, phenyl or benzyl.
  • substituted ammonium ions comprise methylammonium, isopropylammonium, dimethylammonium, diisopropylammonium, trimethylammonium, tetramethylammonium, tetraethylammonium, tetrabutylammonium, 2- hydroxyethylammonium, 2-(2-hydroxyethoxy)ethyl-ammonium, bis(2-hydroxyethyl)ammonium, benzyltrimethylammonium and benzyltriethylammonium, furthermore phosphonium ions, sulfonium ions, preferably tri(Ci-C 4 -alkyl)sulfonium, and sulfoxonium ions, preferably tri(Ci-C 4 - alkyl)sulfoxonium.
  • Anions of useful acid addition salts are primarily chloride, bromide, fluoride, hydrogen sulfate, sulfate, dihydrogen phosphate, hydrogen phosphate, phosphate, nitrate, hydrogen carbonate, carbonate, hexafluorosilicate, hexafluorophosphate, benzoate, and the anions of Ci-C 4 -alkanoic acids, preferably formate, acetate, propionate and butyrate. They can be formed by reacting the compounds of the formulae I with an acid of the corresponding anion, preferably of hydrochloric acid, hydrobromic acid, sulfuric acid, phosphoric acid or nitric acid.
  • the compound of formula (I) may be present in the form of their N-oxides.
  • the term“N-oxide” includes any compound of the present invention which has at least one tertiary nitrogen atom that is oxidized to an N-oxide moiety.
  • N-oxides of compounds (I) can in particular be prepared by oxidizing the ring nitrogen atom(s) of the pyridine ring and/or the pyrazole ring with a suitable oxidizing agent, such as peroxo carboxylic acids or other peroxides.
  • a suitable oxidizing agent such as peroxo carboxylic acids or other peroxides.
  • the compounds of the present invention may be amorphous or may exist in one or more different crystalline states (polymorphs) which may have different macroscopic properties such as stability or show different biological properties such as activities.
  • the present invention includes both amorphous and crystalline compounds of formula (I), their enantiomers or diastereomers, mixtures of different crystalline states of the respective compound of formula (I), its enantiomers or diastereomers, as well as amorphous or crystalline salts thereof.
  • isotopic forms or “isotopically labeled forms” is a general term used for isotopic forms of compounds of formula, wherein one or more atoms of compounds of formula (I) are replaced by their respective isotopes. All isotopes of any particular atom or element as specified are contemplated within the scope of the compounds of the invention.
  • isotopes that may be incorporated into the compounds disclosed herein include, but are not limited to, isotopes of hydrogen such as 2 H (deuterium or D) and 3 H, carbon such as 11 C, 13 C and 14 C, nitrogen such as 13 N and 15 N, oxygen such as 15 0, 17 0 and 18 0, chlorine such as 36 CI, fluorine such as 18 F and sulphur such as 35 S.
  • isotopic forms of the compounds of formula (I) may include, without limitation, deuterated compounds of formula (I).
  • deuterated as used herein, by itself or used to modify a compound or group, refers to replacement of one or more hydrogen atom(s), which is attached to carbon(s), with a deuterium atom.
  • co-crystal denotes a complex of the compounds according to the invention or a stereoisomer, salt, tautomer or N-oxide thereof, with one or more other molecules (preferably one molecule type), wherein usually the ratio of the compound according to the invention and the other molecule is a stoichiometric ratio.
  • solvate denotes a co-complex of the compounds according to the invention, or a stereoisomer, salt, tautomer or N-oxide thereof, with solvent molecules.
  • the solvent is usually liquid. Examples of solvents are methanol, ethanol, toluol, xylol.
  • a preferred solvent which forms solvates is water, which solvates are referred to as“hydrates”.
  • a solvate or hydrate is usually characterized by the presence of a fixed number of n molecules solvent per m molecules compound according to the invention.
  • active compound denotes one or more compound selected from GST inhibitor compound of formula (I) and/or insecticide and/or herbicide.
  • compound(s) of the invention denotes at least one GST inhibitor compound of formula (I).
  • pesticidally active compound denotes one or more compound selected from insecticide and/or biopesticide and/or herbicide.
  • Agronomically acceptable salts of the compound(s) of formula (I) can be formed in a customary manner, e.g. by reaction with an acid of the anion in question.
  • resistance therefore means that the original activity of a pesticide against the target organisms (arthropods, insects) decreases or is even lost, due to genetic adaptation of the target organism.
  • “Resistant” to an insecticide and/or herbicide is understood to mean resistant to at least one insecticide and/or herbicide respectively, i.e. the insect and/or undesired vegetation may be resistant to only one, but also to several insecticides and/or herbicide respectively.
  • the resistance may be also against an insecticidal effect which is due to a genetic modification of a plant (modified or transgenic plant), which caused a resistance of the plant or crop to certain pests, especially insect pests, in susceptible insects.
  • thuringiensis such as endotoxins, e. g. CrylA(b), CrylA(c), CrylF, CrylF(a2), CryllA(b), CrylllA, CrylllB(bl) or Cry9c; vegetative insecticidal proteins (VIP), e. g. VIP1 , VIP2, VIP3 or VIP3A; insecticidal proteins of bacteria colonizing nematodes, for example Photorhabdus spp. or Xenorhabdus spp., and so on.
  • VIP vegetative insecticidal proteins
  • the compounds of formula (I) of the present invention can be applied in form of compositions comprising them as defined above. Furthermore, the compounds of the present invention can be applied together with a mixing partner as defined above or in form of compositions comprising said mixtures as defined above.
  • the components of said mixture can be applied simultaneously, jointly or separately, or in succession, that is immediately one after another and thereby creating the mixture“in situ” on the desired location, e.g. the plant, the sequence, in the case of separate application, generally not having any effect on the result of the control measures.
  • the application can be carried out both before and after the infestation of the crops, plants, plant propagation materials, such as seeds, soil, or the area, material or environment by the pests.
  • Suitable application methods include inter alia soil treatment, seed treatment, in furrow applica tion, and foliar application.
  • Soil treatment methods include drenching the soil, drip irrigation (drip application onto the soil), dipping roots, tubers or bulbs, or soil injection.
  • Seed treatment tech niques include seed dressing, seed coating, seed dusting, seed soaking, and seed pelleting.
  • furrow applications typically include the steps of making a furrow in cultivated land, seeding the furrow with seeds, applying at least one compound of formula (I) and pesticidally active compound to the furrow, and closing the furrow.
  • Foliar application refers to the application of the compound of formula (I) and pesticidally active compound to plant foliage, e.g. through spray equipment.
  • pheromones for specific crops and pests are known to a skilled person and publicly available from databases of pheromones and semiochemicals, such as http://vvww.pherobase.com.
  • contacting includes both direct contact (applying the com
  • habitat breeding ground, plant, seed, soil, area, material or environment in which a pest is growing or may grow, of the animal pest or plant).
  • animal pest includes arthropods, gastropods, and nematodes.
  • Preferred animal pests according to the invention are arthropods, preferably insects and arachnids, in particular insects.
  • Insects, which are of particular relevance for crops, are typically referred to as crop insect pests.
  • crop refers to both, growing and harvested crops.
  • plant includes cereals, e.g. durum and other wheat, rye, barley, triticale, oats, rice, or maize (fodder maize and sugar maize / sweet and field corn); beet, e.g. sugar beet or fodder beet; fruits, such as pomes, stone fruits or soft fruits, e.g.
  • iceberg lettuce chicory, cabbage, asparagus, cabbages, carrots, onions, garlic, leeks, tomatoes, potatoes, cucurbits or sweet peppers; lauraceous plants, such as avocados, cinnamon or camphor; energy and raw material plants, such as corn, soybean, rapeseed, sugar cane or oil palm; tobacco; nuts, e.g. walnuts; pistachios; coffee; tea; bananas; vines (table grapes and grape juice grape vines); hop; sweet leaf (also called Stevia); natural rubber plants or ornamental and forestry plants, such as flowers (e.g. carnation, petunias,
  • geranium/pelargoniums pansies and impatiens
  • shrubs broad-leaved trees (e.g. poplar) or evergreens, e.g. conifers; eucalyptus; turf; lawn; grass such as grass for animal feed or ornamental uses.
  • Preferred plants include potatoes sugar beets, tobacco, wheat, rye, bar-ley, oats, rice, corn, cotton, soybeans, rapeseed, legumes, sunflowers, coffee or sugar cane; fruits; vines; ornamentals; or vegetables, such as cucumbers, tomatoes, beans or squashes.
  • plant is to be understood as including wild type plants and plants, which have been modified by either conventional breeding, or mutagenesis or genetic engineering, or by a combi nation thereof. Plants, which have been modified by mutagenesis or genetic engineering, and are of particular commercial importance, include alfalfa, rapeseed (e.g. oilseed rape), bean, carnation, chicory, cotton, eggplant, eucalyptus, flax, lentil, maize, melon, papaya, petunia, plum, poplar, potato, rice, soybean, squash, sugar beet, sugarcane, sunflower, sweet pepper, tobacco, tomato, and cereals (e.g. wheat), in particular maize, soybean, cotton, wheat, and rice.
  • rapeseed e.g. oilseed rape
  • one or more genes have been mutagenized or integrated into the genetic material of the plant.
  • the one or more mutagenized or inte-grated genes are preferably selected from pat, epsps, cry1 Ab, bar, cry1 Fa2, crylAc, cry34Ab1 , cry35AB1 , cry3A, cryF, cry1 F, mcry3a, cry2Ab2, cry3Bb1 , cry1A.105, dfr, barnase, vip3Aa20, barstar, als, bxn, bp40, asn1 , and ppo5.
  • the mutagenesis or integration of the one or more genes is performed in order to improve certain properties of the plant. Such properties, also known as traits, include abiotic stress tolerance, altered
  • herbicide tolerance e.g. imidazolinone tolerance, glyphosate tolerance, or glufosinate tolerance
  • herbicide tolerance is of particular importance.
  • Several plants have been rendered tolerant to herbicides by mutagenesis, for example Clearfield® oilseed rape being tolerant to imidazolinones, e.g. imazamox.
  • genetic engineering methods have been used to render plants, such as soybean, cotton, corn, beets and oil seed rape, tolerant to herbicides, such as glyphosate and glufosinate, some of which are
  • Insect resistance is typically achieved by modifying plants by integrating cry and/or vip genes, which were isolated from Bacillus thurin- giensis (Bt), and code for the respective Bt toxins. Genetically modified plants with insect re sistance are commercially available under trade names including WideStrike®, Bollgard®, Agri- sure®, Herculex®, YieldGard®, Genuity®, and Intacta®. Plants may be modified by
  • mutagenesis or genetic engineering either in terms of one property (singular traits) or in terms of a combination of properties (stacked traits).
  • Stacked traits e.g. the combination of herbicide tolerance and insect resistance, are of increasing importance.
  • all relevant modified plants in connection with singular or stacked traits as well as detailed information as to the mutagenized or integrated genes and the respective events are available from websites of the organizations“International Service for the Acquisition of Agri-biotech Applications (ISAAA)” (http://www.isaaa.org/gmapprovaldatabase) and“Center for Environmental Risk Assessment (CERA)” (http://cera-gmc.org/GMCropDatabase).
  • the compounds of the present invention are suitable for preventing insects to become resistant to the insecticidal trait or for combating pests, which already have become resistant to the insecticidal trait of a plant and/or modified plant.
  • plant propagation material refers to all the generative parts of the plant such as seeds and vegetative plant material such as cuttings and tubers (e.g. potatoes), which can be used for the multiplication of the plant. This includes seeds, roots, fruits, tubers, bulbs, rhizomes, shoots, sprouts and other parts of plants. Seedlings and young plants, which are to be transplanted after germination or after emergence from soil, may also be included. These plant propagation materials may be treated prophylactically with a plant protection compound either at or before planting or transplanting.
  • seed embraces seeds and plant propagules of all kinds including but not limited to true seeds, seed pieces, suckers, corms, bulbs, fruit, tubers, grains, cuttings, cut shoots and the like, and means in a preferred embodiment true seeds.
  • pesticide refers to insecticides and/or herbicides.
  • esticidally effective amount means the amount of active ingredient needed to achieve an observable effect on growth, including the effects of necrosis, death, retardation, prevention, and removal, destruction, or otherwise diminishing the occurrence and activity of the target organism.
  • the pesticidally effective amount can vary for the various combinations of the target organism.
  • a pesticidally effective amount of the compositions will also vary according to the prevailing conditions such as desired pesticidal effect and duration, weather, target species, locus, mode of application, and the like.
  • the quantity of active ingredients ranges from 0.0001 to 500 g per 100 m2, preferably from 0.001 to 20 g per 100 m2.
  • the rate of application of the active in gredients of this invention may be in the range of 0.0001 g to 4000 g per hectare, e.g. from 1 g to 2 kg per hectare or from 1 g to 750 g per hectare, desirably from 1 g to 100 g per hectare, more desirably from 10 g to 50 g per hectare, e.g., 10 to 20 g per hectare, 20 to 30 g per hectare, 30 to 40 g per hectare, or 40 to 50 g per hectare.
  • the compounds of the formula (I) of invention are particularly suitable for use in the treatment of seeds in order to protect the seeds from insect pests, in particular from soil-living insect pests, and the resulting seedling’s roots and shoots against soil pests and foliar insects.
  • the invention therefore also relates to a method for the protection of seeds from insects, in particular from soil insects, and of the seedling's roots and shoots from insects, in particular from soil and foliar insects, said method comprising treating the seeds before sowing and/or after pregermination with a composition comprising at least one GST inhibitor compound of formula (I) of the invention and at least one active ingredient selected from insecticide and/or herbicide.
  • the protection of the seedling's roots and shoots is preferred. More preferred is the protection of seedling’s shoots from piercing and sucking insects, chewing insects and nematodes.
  • seed treatment comprises all suitable seed treatment techniques known in the art, such as seed dressing, seed coating, seed dusting, seed soaking, seed pelleting, and in-furrow application methods.
  • seed treatment application of the compound of formula (I) is carried out by spraying or by dusting the seeds before sowing of the plants and before emergence of the plants.
  • the invention also comprises seeds coated with or containing at least one GST inhibitor compound of formula (I) of the invention and atleast one active ingredient selected from insecticide and/or herbicide.
  • coated with and/or containing generally signifies that the active ingredients are for the most part on the surface of the propagation product at the time of application, although a greater or lesser part of the ingredient may penetrate into the propagation product, depending on the method of application. When the said propagation product is (re)planted, it may absorb the active ingredients.
  • Suitable seed is for example seed of cereals, root crops, oil crops, vegetables, spices, ornamentals, for example seed of durum and other wheat, barley, oats, rye, maize (fodder maize and sug-ar maize / sweet and field corn), soybeans, oil crops, crucifers, cotton, sunflowers, bananas, rice, oilseed rape, turnip rape, sugarbeet, fodder beet, eggplants, potatoes, grass, lawn, turf, fodder grass, tomatoes, leeks, pumpkin/squash, cabbage, iceberg lettuce, pepper, cucumbers, melons, Brassica species, melons, beans, peas, garlic, onions, carrots, tuberous plants such as potatoes, sugar cane, tobacco, grapes, petunias,
  • the at least one GST inhibitor compound of formula (I) of the invention may also be used for the treatment of seeds from plants, which have been modified by mutagenisis or genetic engineering, and which e.g. tolerate the action of herbicides or insecticides. Such modified plants have been described in detail above.
  • Conventional seed treatment formulations include for example flowable concentrates FS, solutions LS, suspoemulsions (SE), powders for dry treatment DS, water dispersible powders for slurry treatment WS, water-soluble powders SS and emulsion ES and EC and gel formulation GF. These formulations can be applied to the seed diluted or undiluted. Application to the seeds is carried out before sowing, either directly on the seeds or after having pregerminated the latter. Preferably, the formulations are applied such that germination is not included.
  • the compounds of formula (I) of the invention concentrations in ready-to-use formulations are preferably from 0.01 to 60% by weight, more preferably from 0.1 to 40 % by weight.
  • a FS formulation is used for seed treatment.
  • a FS formulation may comprise 1-800 g/l of active ingredient selected from at least one GST inhibitor compound of formula (I) and at least one insecticide and/or herbicide, 1-200 g/l Surfactant, 0 to 200 g/l antifreezing agent, 0 to 400 g/l of binder, 0 to 200 g/l of a pigment and up to 1 liter of a solvent, preferably water.
  • Especially preferred FS formulations of the compounds of the invention for seed treatment usu ally comprise from 0.1 to 80% by weight (1 to 800 g/l) of the active ingredient selected from at least one GST inhibitor compound of formula (I) and at least one insecticide and/or herbicide, from 0.1 to 20 % by weight (1 to 200 g/l) of at least one surfactant, e.g. 0.05 to 5 % by weight of a wetter and from 0.5 to 15 % by weight of a dispersing agent, up to 20 % by weight, e.g. from 5 to 20 % of an anti-freeze agent, from 0 to 15 % by weight, e.g.
  • a pigment and/or a dye from 0 to 40 % by weight, e.g. 1 to 40 % by weight of a binder (sticker /adhesion agent), optionally up to 5 % by weight, e.g. from 0.1 to 5 % by weight of a thickener, optionally from 0.1 to 2 % of an anti-foam agent, and optionally a preservative such as a biocide, antioxidant or the like, e.g. in an amount from 0.01 to 1 % by weight and a filler/vehicle up to 100 % by weight.
  • a binder sticker /adhesion agent
  • a preservative such as a biocide, antioxidant or the like
  • the application rates of the compounds of formula (I) of the invention are generally from 0.1 g to 10 kg per 100 kg of seed, preferably from 1 g to 5 kg per 100 kg of seed, more preferably from 1 g to 1000 g per 100 kg of seed and in particular from 1 g to 200 g per 100 kg of seed, e.g. from 1 g to 100 g or from 5 g to 100 g per 100 kg of seed.
  • the invention therefore also relates to seed comprising a compound of the invention, or an agri culturally useful salt thereof, as defined herein.
  • the amount of the compound of the invention or the agriculturally useful salt thereof will in general vary from 0.1 g to 10 kg per 100 kg of seed, preferably from 1 g to 5 kg per 100 kg of seed, in particular from 1 g to 1000 g per 100 kg of seed. For specific crops such as lettuce the rate can be higher.
  • the present invention provides a method of controlling insects, which are resistant to an insecticide, which method comprises applying to said insecticide resistant insects a composition comprising at least one glutathione S-transferase (GST) inhibitor of formula (I), in free form or an acceptable salt, stereoisomers, an isotopic form, N-oxide, a derivative or mixture thereof and the insecticide, towards which insects are resistant.
  • GST glutathione S-transferase
  • the present invention provides a method of protecting a crop of useful plants susceptible to and/or under attack by insects, which are resistant to an insecticide, which method comprises applying to said crop, treating a plant propagation material of said crop with, and/or applying to said insecticide resistant insects, a composition comprising at least one glutathione S-transferase (GST) inhibitor of formula (I), in free form or an acceptable salt, stereoisomers, an isotopic form, N-oxide, a derivative or mixture thereof and the insecticide, towards which insects are resistant.
  • GST glutathione S-transferase
  • the present invention provides a method of controlling resistance to one or more insecticides in insects, which comprises alternately or simultaneously applying glutathione S-transferase (GST) inhibitor of formula (I) in free form or an acceptable salt, stereoisomers, an isotopic form, N-oxide, a derivative or mixture thereof, and the insecticide, towards which the insects are resistant, to said insects or to a crop of useful plants susceptible to and/or under attack from said insects.
  • GST glutathione S-transferase
  • the present invention provides a method, which process comprises treating the insect, the plant, or the plant propagation material selected from the group consisting of seeds, roots, fruits, tubers, bulbs, rhizomes, shoots, sprouts and other parts of plants, including seedlings and young plants to be protected against insect attack, the stored materials or harvest, or alternately, the locus or soil or soil substituents or surfaces therefrom, with an effective amount of at least one glutathione S-transferase (GST) inhibitor of formula (I) or an acceptable salt, stereoisomers, an isotopic form, N-oxide, a derivative or mixture thereof and the insecticide, towards which insects are resistant.
  • GST glutathione S-transferase
  • the present invention provides a method, wherein the step of treating the seed is followed by a treatment of the emerged host plants with a composition comprising at least one glutathione S-transferase (GST) inhibitor of formula (I), in free form or an acceptable salt, stereoisomers, an isotopic form, N-oxide, a derivative or mixture thereof and the insecticide, towards which insects are resistant.
  • GST glutathione S-transferase
  • I RAC Insecticide Resistance Action Committee
  • M.1 Acetylcholine esterase (AChE) inhibitors M.1A carbamates, e.g. aldicarb, alanycarb, bendio-carb, benfuracarb, butocarboxim, butoxycarboxim, carbaryl, carbofuran, carbosulfan, ethiofen-carb, fenobucarb, formetanate, furathiocarb, isoprocarb, methiocarb, methomyl, metolcarb, oxamyl, pirimicarb, propoxur, thiodicarb, thiofanox, trimethacarb, XMC, xylylcarb and triazamate; or M.1 B organophosphates, e.g.
  • methamidophos methidathion, mevinphos, mono-crotophos, naled, omethoate, oxydemeton- methyl, parathion, parathion-methyl, phenthoate, phor-ate, phosalone, phosmet, phosphamidon, phoxim, pirimiphos- methyl, profenofos, propetamphos, prothiofos, pyraclofos, pyridaphenthion, quinalphos, sulfotep, tebupirimfos, temephos, terbufos, tetrachlorvinphos, thiometon, triazophos, trichlorfon, and vamidothion;
  • GABA-gated chloride channel antagonists M.2A cyclodiene organochlorine compounds, e.g. endosulfan or chlordane; or M.2B fiproles (phenylpyrazoles), e.g. ethiprole, fipronil, flufiprole, pyrafluprole, and pyriprole;
  • M.3 Sodium channel modulators from the class of M.3A pyrethroids e.g. acrinathrin, allethrin, d- cis-trans allethrin, d-trans allethrin, bifenthrin, bioallethrin, bioallethrin S-cylclopentenyl, bio- resmethrin, cycloprothrin, cyfluthrin, beta-cyfluthrin, cyhalothrin, lambda-cyhalothrin, gamma- cyhalothrin, cypermethrin, alpha-cypermethrin, beta-cypermethrin, theta-cypermethrin, zeta- cypermethrin, cyphenothrin, deltamethrin, empenthrin, esfenvalerate, etofen
  • M.4 Nicotinic acetylcholine receptor agonists M.4A neonicotinoids, e.g. acetamiprid, clothianidin, cycloxaprid, dinotefuran, imidacloprid, nitenpyram, thiacloprid and thiamethoxam; or the compounds M .4A.1 4,5-Dihydro-N-nitro-1 -(2-oxiranylmethyl)-1 H-imidazol-2-amine , M.4A.2: (2E-)-1 -[(6-Chloropyridin-3-yl)methyl]-N'-nitro-2-pentylidenehydrazinecarboximidamide; or M4.A.3: 1-[(6-Chloropyridin-3-yl)methyl]-7-methyl-8-nitro-5-propoxy-1 , 2, 3, 5,6,7- hexahydroimidazo[1 ,2-a]pyridine
  • M.7 Juvenile hormone mimics such as M.7A juvenile hormone analogues hydroprene, kinoprene, and methoprene; or M.7B fenoxycarb, or M.7C pyriproxyfen;
  • M.8 miscellaneous non-specific (multi-site) inhibitors e.g. M.8A alkyl halides as methyl bromide and other alkyl halides, M.8B chloropicrin, M.8C sulfuryl fluoride, M .8D borax, or M.8E tartar emetic;
  • M.9 Chordotonal organ TRPV channel modulators e.g. M.9B pymetrozine; pyrifluquinazon;
  • M.10 Mite growth inhibitors e.g. M.10A clofentezine, hexythiazox, and diflovidazin, or M .10B etoxazole;
  • M.1 1 Microbial disruptors of insect midgut membranes, e.g. bacillus thuringiensis or bacillus sphaericus and the insecticdal proteins they produce such as bacillus thuringiensis subsp. is- raelensis, bacillus sphaericus, bacillus thuringiensis subsp. aizawai, bacillus thuringiensis subsp. kurstaki and bacillus thuringiensis subsp. tenebrionis, or the Bt crop proteins: CrylAb, Cryl Ac, Cryl Fa, Cry2Ab, mCry3A, Cry3Ab, Cry3Bb, and Cry34/35Ab1 ;
  • M.12 Inhibitors of mitochondrial ATP synthase e.g. M.12A diafenthiuron, or M.12B organotin miti-cides such as azocyclotin, cyhexatin, or fenbutatin oxide, M.12C propargite, or M.12D tetrad ifon;
  • chlorfenapyr DNOC, or sulfluramid
  • Nicotinic acetylcholine receptor (nAChR) channel blockers e.g. nereistoxin analogues ben-sultap, cartap hydrochloride, thiocyclam, or thiosultap sodium;
  • M.15 Inhibitors of the chitin biosynthesis type 0, such as benzoylureas e.g. bistrifluron, chlorfluazuron, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, teflubenzuron, or triflumuron;
  • benzoylureas e.g. bistrifluron, chlorfluazuron, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, teflubenzuron, or triflumuron;
  • M.16 Inhibitors of the chitin biosynthesis type 1 e.g. buprofezin;
  • Ecdyson receptor agonists such as diacylhydrazines, e.g. methoxyfenozide, tebufenozide, halofenozide, fufenozide, or chromafenozide;
  • Octopamin receptor agonists e.g. amitraz
  • M.20 Mitochondrial complex III electron transport inhibitors e.g. M.20A hydramethylnon, M.20B acequinocyl, M.20C fluacrypyrim; or M.20D bifenazate
  • M.21 Mitochondrial complex I electron transport inhibitors e.g. M.21A METI acaricides and insec-ticides such as fenazaquin, fen pyroxi mate, pyrimidifen, pyridaben, tebufenpyrad or tolfenpyrad, or M.21 B rotenone;
  • M.22 Voltage-dependent sodium channel blockers e.g. M.22A indoxacarb, M.22B
  • M.22B.1 2-[2-(4-Cyanophenyl)-1-[3-(trifluoromethyl)phenyl]-'ethylidene]-N-[4- (difluoromethoxy)phenyl]-hydrazinecarboxamide or M.22B.2: N-(3-Chloro-2-methyhphenyl)-2- [(4-chlorophenyl)[4-[methyl(methylsulfonyl)amino]phenyl]- , methylene]-hydrazinecarboxamide; M.23 Inhibitors of the of acetyl CoA carboxylase, such as Tetronic and Tetramic acid derivatives, e.g. spirodiclofen, spiromesifen, or spirotetramat; M.23.1 spiropidion
  • M.24 Mitochondrial complex IV electron transport inhibitors e.g. M.24A phosphine such as alu minium phosphide, calcium phosphide, phosphine or zinc phosphide, or M.24B cyanide;
  • Mitochondrial complex II electron transport inhibitors such as beta-ketonitrile derivatives, e.g. cyenopyrafen or cyflumetofen;
  • M.28 Ryanodine receptor-modulators from the class of diamides e.g. flubendiamide, chlor- antraniliprole, cyantraniliprole, tetraniliprole, M.28.1 : (R)-3-Chlor-N 1 - ⁇ 2-methyl-4-[1 ,2,2,2 - tetrafluoro-1-(trifluoromethyl)ethyl]phenyl ⁇ -N2-(1-methyl-2-methylsulfonylethyl)phthalamid,
  • M .28.2 (S)-3-Chloro-N 1 - ⁇ 2-methyl-4-[1 ,2,2,2-tetrafluoro-1 -(trifluoromethyl)ethyl]phenyl ⁇ -N2-(1 - methyl-2-methylsulfonylethyl)phthalamid
  • M.28.3 cyclaniliprole
  • M.28.4 methyl-2-[3,5- dibromo-2-( ⁇ [3-bromo-1 -(3-chlorpyridin-2-yl)-1 H-pyrazol-S-yllcarbonyl ⁇ aminoJbenzoylJ-l ,2- dimethylhydrazine-carboxylate; or M.28.5a) N-[4,6-dichloro-2-[(diethyl-lambda-4- sulfanylideneJ-'carbamoylJ-phenylJ ⁇ S-chloro ⁇ -pyridy -S-i
  • M.29 Chordotonal organ Modulators - undefined target site, e.g. flonicamid;
  • M.UN. insecticidal active compounds of unknown or uncertain mode of action e.g. afido-'pyro- pen, afoxolaner, azadirachtin, amidoflumet, benzoximate, broflanilide, bromopropylate, chinomethionat, cryolite, dicloromezotiaz , dicofol, flufenerim, flometoquin, fluensulfone, fluhexafon, fluopyram, fluralaner , metoxadiazone, piperonyl butoxide, pyflu-bumide, pyridalyl, tioxazafen, M .UN .3: 1 1-(4-chloro-2,6-dimethylphenyl)-12-hydroxy- 1 ,4-dioxa-9- azadispiro[4.2.4.2]-tetradec-1 1 -en-10-one ,
  • M.UN.4 3-(4’-fluoro-2,4-dimethylbiphenyl-3-yl)-4-hydroxy-8-oxa-1-azaspiro[4.5]dec-3-en-2-one
  • M.UN.5 1-[2-fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulfinyl]phenyl]-3-(trifluoromethyl)-1 H-1 ,2,4- triazole-5-amine, or actives on basis of bacillus firmus (Votivo, 1-1582);
  • M.UN.8 fluazaindolizine
  • M .UN.9.a) 4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4H-isoxazol- 3-yl]-2-methyl-N-(1 -oxothietan-3-yl)benzamide
  • M.UN.1 1.f) 4-fluoro-N-[2-fluoro-3-[[[2-iodo-4-[1 ⁇ -tetrafluoro-Htrifluoromethyl ⁇ ethyll-B- (trifluoromethyl)phenyl]annino]carbonyl]phenyl]-N-methyl-benzamide; M.UN.1 1.g) 3-fluoro-N-[2- fluoro-S- ⁇ -iodo ⁇ -ll ⁇ -tetrafluoro-l-itrifluoromethy -'ethyll-e-
  • M. UN.14a 1 -[(6-Chloro-3-pyridinyl)methyl]-1 ,2,3,5,6,7-hexahydro-5-methoxy-7-methyl-8-nitro- imidazo[1 ,2-a]pyridine; or M. UN.14b) 1-[(6-Chloropyridin-3-yl)methyl]-7-methyl-8-nitro- 1 ,2,3,5,6,7-hexahydroimidazo[1 ,2-a]pyridin-5-ol;
  • M. UN.16a 1 -isopropyl-N,5-dimethyl-N-pyridazin-4-yl-pyrazole-4-carboxamide; or M. UN.16b) 1 - (1 ,2-dimethylpropyl)-N-ethyl-5-methyl-N-pyridazin-4-yl-pyrazole-4-carboxamide; M. UN.16c)
  • M.UN.16d 1 -[1 -(1-cyanocyclopropyl)ethyl]-N-ethyl-5-methyl-N-pyridazin-4-yl-pyrazole-4- carboxamide
  • M.UN.16e N-ethyl-1 -(2-fluoro-1-methyl-propyl)-5-methyl-N-pyridazin-4-yl- pyrazole-4-carboxamide
  • M.UN.16f 1 -(1 ,2-dimethylpropyl)-N,5-dimethyl-N-pyridazin-4-yl- pyrazole-4-carboxamide
  • M .UN.16g 1 -[1-(1-cyanocyclopropyl)ethyl]-N,5-dimethyl-N-pyridazin- 4-yl-pyrazole-4-carboxamide
  • M .U N .16h N-methyl-1 -(2-fluoro-1 -methyl
  • M. UN.17a N-(1-methylethyl)-2-(3-pyridinyl)-2H-indazole-4-carboxamide
  • M. UN.17b N- cyclopropyl-2-(3-pyridinyl)-2H-indazole-4-carboxamide
  • M. UN.18a N-[3-chloro-1 -(3-pyridyl)pyrazol-4-yl]-N-ethyl-3-(3,3,3- trifluoropropylsulfanyl)propanamide
  • M. UN.18b N-[3-chloro-1-(3-pyridyl)pyrazol-4-yl]-N-ethyl-3- (3,3,3-trifluoropropylsulfinyl)propanamide
  • M.UN .21 N-[4-Chloro-3-[[(phenylmethyl)amino]carbonyl]phenyl]-1-methyl-3-(1 ,1 ,2,2,2- pentafluoroethyl)-4-(trifluoromethyl)-1 H-pyrazole-5-carboxamide ;
  • M. UN.22a 2-(3-ethylsulfonyl- 2-pyridyl)-3-methyl-6-(trifluoromethyl)imidazo[4,5-b]pyridine, or M. UN.22b 2-[3-ethylsulfonyl-5- (trifluoromethyl)-2-pyridyl]-3-methyl-6-(trifluoromethyl)imidazo[4,5-b]pyridine ;
  • M. UN.23a 4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4H-isoxazol-3-yl]-N-[(4R)-2-ethyl-3-oxo- isoxazolidin-4-yl]-2-methyl-benzamide, or M. UN.23b 4-[5-(3,5-dichloro-4-fluoro-phenyl)-5- (trifluoromethyl)-4H-isoxazol-3-yl]-N-[(4R)-2-ethyl-3-oxo-isoxazolidin-4-yl]-2-methyl-benzamide ; M.
  • M.4 cycloxaprid is known from WO2010/069266 and WO201 1/069456.
  • M.4A.1 is known from CN 103814937; CN 105367557, CN 105481839.
  • M.4A.2, guadipyr is known from WO 2013/003977, and M.4A.3 (approved as paichongding in China) is known from WO
  • M.22B.1 is described in CN 10171577 and M.22B.2 in CN 102126994.
  • Spiropidion M.23.1 is known from WO 2014/191271.
  • M .28.1 and M .28.2 are known from W02007/101540.
  • M.28.3 is described in W02005/077934.
  • M.28.4 is described in W02007/043677.
  • M .28.5a) to M.28.5d) and M.28.5h) are described in WO 2007/006670, WO2013/024009 and WO
  • M.28.5i is described in WO2011/085575, M.28.5j) in W02008/134969, M.28.5k) in US2011/046186 and M .28.5I) in WO2012/034403.
  • M.28.6 can be found in WO2012/034472.
  • M.UN.3 is known from W02006/089633 and M.UN.4 from W02008/067911.
  • M.UN.5 is descrhbed in W02006/043635, and biological control agents on the basis of bacillus firmus are described in W02009/124707. Flupyrimin is described in WO2012/029672.
  • M.U N.8 is known from WO2013/055584.
  • M .UN .9.a is described in WO2013/050317.
  • M.UN.9.b is described in WO2014/126208.
  • M.UN.10 is known from WO2010/060379. Broflanilide and M.UN.1 1.b) to M.UN.1 1.h) are described in W02010/018714, and M.UN.11 i) to M.UN.1 1 .p) in WO
  • M.UN.12.a) to M.UN.12.C) are known from WO2010/006713
  • M.UN.12.d) and M.UN.12.e) are known from WO2012/000896, and M.UN.12.f) to M.UN.12.m) from WO 2010/129497 .
  • M.UN.14a) and M.U N.14b) are known from W02007/101369.
  • M.UN.16.a) to M.UN.16h) are de-scribed in WO2010/034737, WO2012/084670, and WO2012/143317, resp., and M.UN.16i) and M.UN.16j) are described in WO2015/055497.
  • M.UN.17a) to M.UN.17 ) are described in WO2015/038503.
  • M. UN.18a) to M.UN.18d) are described in US2014/0213448.
  • M.UN.19 is de-scribed in WO2014/036056.
  • M.UN.20 is known from WO2014/090918.
  • M.UN.21 is known from EP2910126.
  • M. UN.22a and M. UN.22b are known from WO2015/059039 and W02015/190316.
  • M.UN.23a and M.UN.23b are known from WO2013/050302.
  • M.UN.24a and M. UN.24b are known from WO2012/126766.
  • Acynonapyr M.U N.25 is known from WO
  • Benzpyrimoxan M .UN.26 is known from W02016/104516.
  • M.UN.27 is known from WO2016174049.
  • the present invention provides a method, wherein the resistant insects developed resistance against insecticides, avermectins, milbemycins, cyclodienes, phosphines, carbamates, pyrethroids, spinosyns, neonicotinoids, diamides, anthranilamide, beta-ketonitrile derivatives, Tetronic and Tetramic acid derivatives, nereistoxin analogues, acaricides, insect growth regulators, or antifeedants.
  • the resistant insects developed resistance against pyrethrums, pyrethroids, spynosins and/or anthranilamide.
  • a method of controlling insects which are resistant to a neonicotinoid insecticide comprises applying a composition comprising at least one GST inhibitor compound of formula (I), in free form or or an acceptable salt, stereoisomers, an isotopic form, N-oxide, a derivative or mixture thereof to said resistant insects and the neonicotinoid insecticide.
  • a method of controlling insects which are resistant to a pyrethroid insecticide such as such as acrinathrin, allethrin, d-cis-trans allethrin, d-trans allethrin, bifenthrin, bioallethrin, bioallethrin S-cylclopentenyl, bioresmethrin, cycloprothrin, cyfluthrin, beta-cyfluthrin, cyhalothrin, lambda-cyhalothrin, gamma-cyhalothrin, cypermethrin, alpha-cypermethrin, beta-cypermethrin, theta-cypermethrin, zeta-cypermethrin, cyphenothrin, deltamethrin, empenthrin, esfenvalerate, et
  • a pyrethroid insecticide
  • composition comprising at least one GST inhibitor compound of formula (I), in free form or or an acceptable salt, stereoisomers, an isotopic form, N-oxide, a derivative or mixture thereof and the pyrethroid insecticide, to said resistant insects.
  • a method of controlling insects which are resistant to an organophosphate insecticide such as primicarb, which method comprises applying a composition comprising at least one GST inhibitor compound of formula (I), in free form or an acceptable salt, stereoisomers, an isotopic form, N-oxide, a derivative or mixture thereof and the organophosphate insecticide, to said resistant insects.
  • a method of controlling insects which are resistant to a feeding blocker insecticide such as pymetrozine, which method comprises applying a composition comprising at least one GST inhibitor compound of formula (I), in free form or an acceptable salt, stereoisomers, an isotopic form, N-oxide, a derivative or mixture thereof and the feeding blocker insecticide, to said resistant insects.
  • the present invention provides a method of controlling insects, which are resistant to an insecticide, are from the order Lepidoptera, from the order Coleoptera, from the order Diptera, from the order Thysanoptera, from the order Hemiptera, from the order
  • Hymenoptera from the order Orthoptera, from the class Arachnida, from the Phylum Nematoda, from the order Isoptera, from the order Blattodea from the order Siphonoptera, from the order Thysanura, from the class Chilopoda, from the class Diplopoda, from the class Symphyla, from the order Dermaptera, from the order Collembola, from the order Isopoda, from the order anoplura, from the Phylum Mollusca or from the order Phthiraptera, which method comprises applying a composition comprising at least one GST inhibitor compound of formula (I), in free form or an acceptable salt, stereoisomers, an isotopic form, N-oxide, a derivative or mixture thereof to said resistant insects and the insecticide, towards which insects are resistant.
  • the method of the present invention control insects of the suborder Lepidoptera, such as Plutella maculipennis, Plutella xylostella, Tricho
  • the method of the present invention control pests of the suborder of Arachnida including Eotetranychus spp., Eutetranychus spp., Oligonychus spp., Petrobia latens, Tetranychus spp. such as T. cinnabarinus, T. evansi, T. kanzawai, T, pacificus, T. phaseulus, T. telarius and T. urticae; Bryobia praetiosa; Panonychus spp. such as P. ulmi, P. citri;
  • in another embodiment of the invention provides a method of controlling species of insects which have shown resistance effects against insecticides, in particular from the order of Hemiptera with their suborder of Homoptera and Heteroptera, but also from the orders
  • Thysanoptera Lepidoptera, Coleoptera or Diptera.
  • the method of the present invention may further control pests of the suborder heteroptera including bugs, such as shield bugs, seed bugs, assassin bugs, flower bugs, stink bugs, sweetpotato bugs and the water bugs.
  • bugs such as shield bugs, seed bugs, assassin bugs, flower bugs, stink bugs, sweetpotato bugs and the water bugs.
  • the invention also provides a method of protecting a crop of useful plants, wherein said crop is susceptible to and/or under attack from insects which are resistant towards insecticide.
  • a method involves applying to said crop, treating a plant propagation material of said crop with, and/or applying to said insects, a composition comprising at least one GST inhibitor compound of formula (I) in free form or an acceptable salt, stereoisomers, an isotopic form, N-oxide, a derivative or mixture thereof and the insecticide, towards which insects are resistant.
  • the GST inhibitor compound of formula (I) of the present invention are effective through both contact and ingestion. Furthermore, the compounds of the present invention can be applied to any and all developmental stages, such as egg, larva, pupa, and adult.
  • the compounds of the present invention are especially suitable for efficiently combating animal pests such as arthropods, gastropods and nematodes including but not limited to:
  • insects from the order of Lepidoptera for example Achroia grisella , Aderis spp. such as A. fimbriana, A. gloxerana, A. variana; Acro!epiopsis assectella, Acronicta major, Adoxophyes spp. such as A. cyrtosema, A. orana; Aedia leucomelas, Agrotis spp. such as A. exdamationis, A. fucosa, A. ipsilon, A. orthogoma, A. segetum, A.
  • Argyresthia conjugella Argyroploce spp., Argyrotaenia spp.
  • A. ve!utinana Athetis mindara, Austroasca viridigrisea, Autographa gamma, Autographa nigrisigna, Barathra brassicae, Bedellia spp., Bonagota salubricola, Borbo dnnara, Buccu!atrix thurberiella, Bupalus piniarius, Busseo/a spp., Cacoecia spp. such as C. murinana, C.
  • Cactoblastis cactorum Cadra cautella, Calingo brazHiensis, Caloptilis theivora, Capua reticu!ana
  • Carposina spp. such as C. niponensis, C. sasakii; Cephusspp., Chaetocnema ariduia, Cheimatobia brumata, C ospp. such as C. /ndicus, C. suppressaiis, C. partellus; Choreutis pariana, Choristoneura spp. such as C. conflictana, C. fumiferana, C. longicellana, C. murinana, C. occidentaHs, C.
  • E cauteiia such as E cauteiia, E eiuteiia, E kuehmaschineia; Epinotia aporema, Epiphyas postvittana, Erannis tiiiaria, Erionota thrax, Etieiia spp., Euiia spp., Eupoeciiia ambiguella, Euproctis chrysorrhoea, Euxoa spp., Evetria bouiiana, Faronta aibiiinea, Feitia spp. such as F. subterranean; Galleria meiioneiia, GraciHaria spp., Graphoiita spp.
  • L coffeeiia, L. sciteiia; Leuminivora iycinivoreiia, Lithocoi/etis biancardeiia, Lithophane antennata, Liattia octo ( Amyna axis), Lobesia botrana, Lophocampa spp., Loxagrotis aibicosta, Loxostege spp. such as L. sticticaiis, L. cereraiis; Lymantria spp. such as L dispar, L monacha; Lyonetia clerkeila, Lyonetia prunifoliella, Maiacosoma spp. such as M. americanum, M.
  • M. constrictum M. neustria
  • Mamestra spp. such as M. brassicae, M. configurata
  • Marasmia spp Marmara spp., Maruca testuiaiis, Megaiopyge ianata, Meianchra picta, Meianitis ieda
  • Mods spp. such as M. iapites, M.
  • nubiiaiis nubiiaiis; Ouiema oryzae, Paieacrita vernata, Panoiis fiammea, Parnara spp., Papaipema nebris, Papiiio cresphontes, Paramyeiois transiteiia, Paranthrene regaiis, Paysandisia archon, Pe inophora spp. such as P. gossypietia; Peridroma saucia, Pierieucoptera spp., such as P. coffeeiia; Phaiera bucephaia, Phryganidia caiifornica, Phthorimaea spp. such as P.
  • opercuieiia Phy/iocnistis citreiia, Phyiionorycter spp. such as P. biancardeiia, P. crataegeiia, P. issikii, P. ringoschoolia; Pieris spp. such as P. brassicae, P. rapae, P. napi; Pi/ocrocis tripunctata, Piathypena scabra, Platynota spp. such as P. fiavedana, P. idaeusalis, P.
  • Tecia soianivora Teiehin iicus
  • Theda spp. Theresimima ampeiophaga, Thyrinteina spp, THdenia inconspicueiia, Tinea spp. such as T cioaceiia, T. pellionella; Tineoia bisseliieiia, Tortrix spp. such as T.
  • Trichophaga tapetzeiia Trichophaga tapetzeiia, Trichopiusia spp. such as T. ni
  • Virachoia pp. Yponomeuta padeiia, and Zeiraphera canadensis;
  • insects from the order of Coleoptera for example Acaiymma vittatum, Acanthoscehdes obtectus, Adoretus spp., Ageiastica aini, Agriius spp. such as A. anxius, A. pianipennis, A. sinuatus; Agriotes spp. such as A. fuscicoiiis, A. iineatus, A.
  • A/phitobius diaperinus Amphimaiius soistitiaiis, Anisandrus dispar, Anisopiia austriaca, Anobium punctatum, Anomaia corpuienta, Anomaia rufocuprea, Anopiophora spp. such as A. giabripennis; Anthonomus spp. such as A. eugenii, A. grandis, A. pomorum; Anthrenus spp., Aphthona euphoridae, Apion spp., Apogonia spp., Athous haemorrhoidaiis, Atomaria spp. such as A.
  • Attagenus spp. Auiacophora femoraiis, Biastophagus piniperda, Biitophaga undata, Bruchidius obtectus, Bruchus spp. such as B. fentis, B. pisorum, B. rufimanus; Byctiscus betuiae, Callidiellum rufipenne, Caiiopistria fioridensis, Caiiosobruchus chinensis, Cameraria ohrideiia, Cassida nebuiosa, Cerotoma trifurcata, Cetonia aurata, Ceuthorhynchus spp. such as C.
  • Curcuiio spp. Cyiindrocopturus spp., Cyciocephaia spp., Dactyiispa baiyi, Dectes texanus, Dermestes spp., Diabroticas pp. such as D. undecimpunctata, D. speciosa, D. iongicornis, D. semipunctata, D.
  • Diaprepes abbreviates, Dichocrocis spp., Diciadispa armigera, Diioboderus abderus, Diocaiandra frumenti (Diocaiandra stigmaticoiiis), Enaphaiodes rufuius, Epiiachna spp. such as E. varivestis, E. vigintioctomacuiata; Epitrix spp. such as E. hirtipennis, E.
  • hypomeces squamosus Hypothenemus spp., ips typographus, Lachnosterna consanguinea, Lasioderma serricorne, Latheticus oryzae, Lathridius spp., Lema spp. such as L biiineata, L. meianopus; Leptinotarsa spp. such as L. decemiineata; Leptispa pygmaea, Limonius caiifornicus, Lissorhoptrus oryzophiius, Lixus spp., Luperodes spp., Lyctus spp.
  • aiternatus Naupactus xanthographus, Niptus ho/o/eucus, Oberia brevis, Oemona hirta, Oryctes rhinoceros, Oryzaephiius surinamensis, Oryzaphagus oryzae, Otiorrhynchus su/catus, Otiorrhynchus ovatus, Otiorrhynchus su/catus, Ouiema meianopus, Ouiema oryzae, Oxycetonia jucunda, Phaedon spp. such as P. brassicae, P.
  • vuineratus Sudperda Candida, Sco/ytus schevyrewi, Scyphophorus acupunctatus, Sitona iineatus, Sitophi/us spp. such as S. granaria, S. oryzae, S. zeamais; Sphenophorus spp. such as S. ievis; Stegobium paniceum, Sternechus spp. such as S. subsignatus; Strophomorphus ctenotus, Symphyietes spp., Tanymecus spp., Tenebrio moiitor, Tenebrioides mauretanicus, Triboiium spp. such as T.
  • Trogoderma spp. Tychius spp.
  • Xyiotrechus spp. such as X. pyrrhoderus
  • Zabrus spp. such as Z. tenebrioides
  • insects from the order of Diptera for example Aedes spp. such as A. aegypti, A. aibopictus, A. vexans; Anastrepha ludens, Anopheles spp. such as A. aibimanus, A. crucians, A. freeborni, A. gambiae, A. ieucosphyrus, A. macuiipennis, A. minimus, A. quadrimacuiatus, A.
  • Aedes spp. such as A. aegypti, A. aibopictus, A. vexans; Anastrepha ludens, Anopheles spp. such as A. aibimanus, A. crucians, A. freeborni, A. gambiae, A. ieucosphyrus, A. macuiipennis, A. minimus, A. quadrimacuiat
  • quinquefasciatus C. tarsaiis, C. tritaeniorhynchus
  • Cu/icoides furens Cuiiseta inornata, Cuiiseta meianura, Cuterebra spp., Dacus cucurbitae, Dacus oieae, Dasineura brassicae, Dasineura oxycoccana, Delia spp. such as D. antique, D. coarctata, D. piatura, D. radicum; Dermatobia hominis, Drosophila spp. such as D. suzukii, Fannia spp. such as F. canicuiaris; Gastraphiius spp. such as G.
  • Geomyza tipunctata, Giossina spp. such as G. fuscipes, G. morsitans, G. paipaiis, G. tachinoides; Haematobia irritans, Hapiodipiosis equestris, Hippeiates spp., Hylemyia spp. such as H. piatura; Hypoderma spp. such as H. iineata; Hyppobosca spp., Hydreiiia phiiippina, Leptoconops torrens, Liriomyza spp. such as L sativae, L. trifoiii; Luciiia spp.
  • L caprina L caprina
  • L. cuprina L. sericata
  • Lycoria pectoralis Mansonia titiiianus, Mayetioia spp.
  • Musca spp. such as M. autumnaiis, M. domestica
  • Muscina stabuians Oestrus spp.
  • Opomyza fiorum Oscineiia spp.
  • O. frit O. frit
  • Orseoiia oryzae Pegomya hysocyami
  • Phiebotomus argentipes Phorbiaspp.
  • P. antiqua P. brassicae, P.
  • T. bovinus T. iineoia, T. simi/is
  • Tannia spp. Thecodip/osis japonensis, Tipuia oieracea, Tipuia paiudosa, and Wohifahrtia spp;
  • insects from the order of Thysanoptera for example, Baiiothrips biformis, Dichromothrips corbetti, Dichromothrips ssp., Echinothrips americanus, Enneothrips Havens, Frankiimaschineia spp. such as F. fusca, F. occidentaiis, F.
  • Heiiothrips spp. Hercinothrips femoraiis, Kakothrips spp., Microcephalothrips abdominalis, Neohydatothrips samayunkur, Pezothrips kellyanus, Rhipiphorothrips cruentatus, Scirtothrips spp. such as S. citri, S. dorsalis, S. perseae; Stenchaetothrips spp, Taeniothrips cardamoni, Taeniothrips inconsequens, Thrips spp. such as T. imagines, T hawaiiensis, T. oryzae, T. paimi, T. parvispinus, T. tabaci;
  • insects from the order of Hemiptera for example, Acizzia jamatonica, Acrosternum spp. such as A. hiiare; Acyrthosipon spp. such as A. onobrychis, A. pisum; Adeiges iaricis, Adeiges tsugae, Adeiphocoris spp., such as A. rapidus, A.
  • B. ieucopterus such as B. ieucopterus; Brachycaudus spp. such as B. cardui, B. heiichrysi, B. persicae, B. prunicoia; Brachycoius spp., Brachycoryneiia asparagi, Brevicoryne brassicae, Cacopsyiia spp. such as C. fuiguraiis, C.
  • Dysmicoccusspp. Edessa pp., Geocoris spp., Empoascaspp. such as E. fabae, E. soiana; Epidiaspis ieperii, Eriosoma spp. such as E. ianigerum, E. pyricoia; Erythroneura spp., Eurygaster spp. such as E. integriceps; Eusceiis bi/obatus, Euschistus spp. such as E. herns, E. impictiventris, E.
  • Nephotettix spp. such as N. maiayanus, N. nigropictus, N. parvus, N. virescens; Nezara spp. such as N. viriduia; Niiaparvata iugens, Nysius huttoni, Oebaius spp. such as O.
  • P. devastatrix Piesma quadrata, Piezodorus spp. such as P. guildinii; Pinnaspis aspidistrae, Planococcus spp. such as P. citri, P. ficus; Prosapia bicincta, ProtopuMnaria pyriformis, Psa/lus seriatus, Pseudacysta persea, Pseudau!acaspis pentagona, Pseudococcus spp. such as P. comstocki; Psylla spp. such as P.
  • Pteroma/us spp. Pu!vinaria amygdaii, PyriHa spp., Quadraspidiotus spp., such as Q. perniciosus; Quesada gigas, Rastrococcus spp., Reduvius senilis, Rhizoecus americanus, Rhodnius spp., Rhopaiomyzus ascaionicus, Rhopaiosiphum spp. such as R. pseudobrassicas, R. insertum, R. maidis, R.
  • Sagatodes spp., Sahibergeiia singuiaris, Saissetia spp., Sappaphis maia, Sappaphis maii, Scaptocoris spp., Scaphoides titanus, Schizaphis graminum, Schizoneura lanuginosa, Scotinophora spp., Seienaspidus articuiatus, Sitobion avenae, Sogata spp., Sogateiia furcifera, Soiubea insularis, Spissistiius festinus ( Stictocephaia festina), Stephanitis nashi, Stephanitis pyrioides, Stephanitis takeyai, Tenaiaphara maiayensis, Tetraieurodes perseae, Therioaphis maculate, Thyanta spp.
  • T. accerra, T perditor such as T. accerra, T perditor; Tibracas ., Tom as pis spp., Toxoptera spp. such as T. aurantii; Triaieurodes spp. such as T. abutiionea, T. ricini, T. vaporariorum; Triatom a spp., Trioza spp., Typhiocybas ., Unaspis spp. such as U. citri, U. yanonensis; and Viteus vitifoiii,
  • Insects from the order Orthoptera for example Acheta domesticus, Caiiiptamus itaiicus, Chortoicetes terminifera, Ceuthophiius spp., Diastrammena asynamora, Dociostaurus maroccanus, Gryiiotaipa spp. such as G. africana, G. gryiiotaipa; Gryiius spp., Hierogiyphus daganensis, Kraussaria anguiifera, Locusta s p. such as L. migratoria, L. pardaiina; Meianopius spp. such as M. bivittatus, M.
  • Pests from the Class Arachnida for example Acari.e.g. of the families Argasidae, Ixodidae and Sarcoptidae, such as Ambiyomma spp. (e.g. A. americanum, A. variegatum, A. macuiatum), Argas spp. such as A. persicu), Boophilus spp. such as B. annuiatus, B. decoloratus, B. microplus, Dermacentor spp. such as D.siivarum, D. andersoni, D. variabilis, Hya/omma spp. such as H. truncatum, Ixodes spp. such as i. ricinus, i.
  • Ambiyomma spp. e.g. A. americanum, A. variegatum, A. macuiatum
  • Argas spp. such as A. persicu
  • Boophilus spp. such as
  • rubicundus i. scapu/aris, I. holocyclus, i. pacificus, Rhipicephalus sanguineus, Ornithodorus spp. such as O. moubata, O. hermsi, O. turicata, Ornithonyssus bacoti, Otobius megnini, Dermanyssus gallinae, Psoroptes spp. such as P. ovis, Rhipicephalus spp. such as R. sanguineus, R. appendicuiatus, Rhipicephalus evertsi, Rhizogiyphus spp.. Sarcoptes spp. such as 5.
  • Scabiei and Family Eriophyidae including Aceria spp. such as A. she/doni, A. anthocoptes, Acaiiitus spp., Acu/ops spp. such as A. iycopersici, A. peiekasst, Acuius spp. such as A. schiechtendaii; Coiomerus vitis, Epitrimerus pyri, Phyiiocoptruta oieivora; Eriophytes ribis and Eriophyes spp.
  • Aceria spp. such as A. she/doni, A. anthocoptes, Acaiiitus spp., Acu/ops spp. such as A. iycopersici, A. peiekasst, Acuius spp. such as A. schiechtendaii; Coiomerus vitis, Epitrimerus pyri, Phyi
  • Haiotydeus destructor Family Demodicidae with species such as Demodex spp.; Family Trombicidea including Trombicuia spp.; Family Cellyssidae including Ornothonyssus spp.; Family Pyemotidae including Pyemotes tritici, Tyrophagus putrescentiae, Family Acaridae including Acarus sira, Family Araneida including Latrodectus mactans, Tegenaria agrestis, Chiracanthium sp, Lycosa sp Achaearanea tepidariorum and Loxosce/es reciusa,
  • Pests from the Phylum Nematoda for example, plant parasitic nematodes such as root-knot nematodes, Meioidogyne spp. such as M. hapia, M. incognita, M. javanica; cyst-forming nematodes, Giobodera spp. such as G. rostochiensis; Heterodera spp. such as H. avenae, H. glycines, H. schachtii, H. trifoiii; Seed gall nematodes, Anguina spp. ⁇ Stem and foliar nematodes, Apheienchoides spp. such as A.
  • Criconemoides spp. such as Criconemoides inform is; Mesocriconema spp.; Stem and bulb nematodes, Dityienchus spp. such as D. destructor, D.
  • Awl nematodes Dotichodorus spp./ Spiral nematodes, Heiiocotyienchus muiticinctus; Sheath and sheathoid nematodes, Hemicyciiophora spp. and Hemicriconemoides spp./ Hirshmanmaschineia spp./ Lance nematodes, Hopioaimus spp./ False rootknot nematodes, Nacobbus spp./ Needle nematodes, Longidorus spp. such as L. eiongatus; Lesion nematodes, Pratyienchus spp. such as P.
  • brachyurus P. negiectus, P. penetrans, P. curvitatus, P. goodeyi; Burrowing nematodes, Radophoius spp. such as R. similis; Rhadophoius spp./ Rhodopho/us spp./ Reniform
  • Rotyienchus spp. such as R. robustus, R. reniformis
  • Scuteiionema spp./ Stubby- root nematode Trichodorus spp. such as T. obtusus, T. primitivus
  • Paratrichodorus spp. such as P. minor
  • Stunt nematodes, Tyienchorhynchus spp. such as T. ciaytoni, T. dubius
  • Citrus nematodes, Tyienchuius spp. such as T.
  • Dagger nematodes Xiphinema spp./ and other plant parasitic nematode species
  • Insects from the order Isoptera for example Caiotermes flavicollis, Coptotermes spp. such as C. formosanus, C. gestroi, C. acinaciformis; Cornitermes cumulans, Cryptotermes spp. such as C. brevis, C. cavifrons; Giobitermes sulfureus, Heterotermes spp. such as H. aureus, H. tongiceps, H. tenuis; Leucotermes fiavipes, Odontotermes spp., incisitermes spp. such as /. minor, i.
  • Neocapritermes spp. such as N. opacus, N. parvus
  • Neotermes spp. Procornitermes spp.
  • Zootermopsis spp. such as Z. angusticoiiis, Z. nevadensis
  • Reticulitermes spp. such as R. hesperus, R. tibialis, R. speratus, R. fiavipes, R. grassei, R. iucifugus, R. santonensis, R. virginicus
  • Termes nataiensis such as M. darwiniensis
  • Neocapritermes spp. such as N. opacus, N. parvus
  • Neotermes spp. Procornitermes spp.
  • Zootermopsis spp. such as Z. angusticoiiis, Z. nevadensis
  • Reticulitermes spp. such as R. hesperus, R. tibialis, R
  • Biatta pp. such as B. orientaiis, B. lateralis; Biatteiia spp. such as B. asahinae, B. germanica; Leucophaea maderae, Panchiora nivea, Peripianeta spp. such as P. americana, P. austraiasiae, P. brunnea, P. fuiigginosa, P. japonica; Supeiia iongipaipa, Parcobiatta pennsyivanica, Eurycotis fioridana, Pycnosceius surinamensis,
  • Insects from the order Siphonoptera for example Cediopsytia simples, Ceratophyiius spp., Ctenocephaiides spp. such as C. feiis, C. canis, Xenopsyiia cheopis, Puiex irritans, Trichodectes canis, Tunga penetrans, and Nosopsyl/us fasciatus,
  • Thysanura for example Lepisma saccharine , Ctenoiepisma urbana, and Thermobia domestica
  • Pests from the class Chilopoda for example Geophiius spp., Scutigera spp. such as Scutigera coieoptrata,
  • Pests from the class Diplopoda for example Bianiuius guttuiatus, Ju/us spp., Narceus spp.,
  • Insects from the order Collembola for example Onychiurus spp., such as Onychiurus armatus, Pests from the order Isopoda for example, Armadiiiidium vuigare, Oniscus ase/ius, Porceiiio scaber,
  • Insects from the order Phthiraptera for example Damaiinia spp., Pediculus spp. such as Pedicu/us humanus capitis, Pedicu/us humanus corporis, Pedicu/us humanus humanus; Pthirus pubis, Haematopinus spp. such as Haematopinus eurysternus, Haematopinus suis, Linognathus spp. such as Linognathus vituii; Bovicoia bovis, Menopon gaiiinae, Menacanthus stramineus and Solenopotes capiiiatus, Trichodectes spp.,
  • Examples of further pest species which may be controlled by compounds of fomula (I) include: from the Phylum Mollusca, class Bivalvia, for example, Dreissena spp. ⁇ class Gastropoda, for example, Arion spp., Biomphaiaria spp., Buiinus spp., Deroceras spp., Gaiba spp., Lymnaea spp., Oncomeiania spp . , Pomacea canaiiciata, Succinea spp.
  • Ancyiostoma duodenaie for example, Ancyiostoma duodenaie, Ancyiostoma ceyianicum, Acyiostoma braziiiensis, Ancyiostoma spp., Ascaris iubricoides, Ascaris spp., Brugia maiayi, Brugia timori, Bunostomum spp., Chabertia spp., C/onorchis spp., Cooperiaspp., Dicrocoeiium spp., Dictyocauius fiiaria, Diphyiiobothrium iatum, Dracuncuius medinensis, Echinococcus granulosus, Echinococcus muitiiocuiaris, Enterobius vermicuiaris, Facio/aspp., Haemonchus spp.
  • Haemonchus contortus such as Haemonchus contortus; Heterakis spp., Hymenoiepis nana, Hyostrongulus spp., Loa Loa, Nematodirus spp., Oesophagostomum spp . , Opisthorchis spp., Onchocerca volvulus, Os tertagia spp.,
  • resistant pest species which may be controlled by use of compounds of formula (I) include: Anisoplia austriaca, Apamea spp., Austroasca viridigrisea, Baliothrips biformis, Caenorhabditis elegans, Cephus spp., Ceutorhynchus napi, Chaetocnema aridula, Chilo auricilius, Chilo indicus , Chilo polychrysus, Chortiocetes terminifera, Cnaphalocroci medinalis, Cnaphalocrosis spp., Colias eurytheme, Collops spp., Cornitermes cumulans, Creontiades spp., Cyclocephala spp., Dalbulus maidis, Deraceras reticulatum , Diatrea saccharalis, Dichelops furcatus, Dicladispa armigera , Diloboderus s
  • Diloboderus abderus such as Diloboderus abderus; Edessa spp., Epinotia spp., Formici-dae, Geocoris spp., Globitermes sulfureus, Gryllotalpidae, Halotydeus destructor, Hipnodes bicolor, Hydrellia philippina, Julus spp., Laodelphax spp., Leptocorsia acuta , Leptocorsia orato-rius , Liogenys fuscus, Lucillia spp., Lyogenys fuscus, Mahanarva spp., Maladera matrida, Ma-rasmia spp., Mastotermes spp., Mealybugs, Megascelis ssp, Metamasius hemipterus, Microtheca spp., Mocis latipes, Murgantia spp., Mythe
  • Orseolia oryzae such as Orseolia oryzae; Oxycaraenus hyalinipennis, Plusia spp., Pomacea canaliculata, Procornitermes ssp, Procornitermes triacifer , Psylloides spp., Rachiplusia spp., Rhodopholus spp., Scaptocoris castanea, Scaptocoris spp., Scirpophaga spp. such as Scirpophaga incertulas , Scirpophaga innotata; Scotinophara spp. such as Scotinophara coarctata; Sesamia spp. such as Sesamia inferens, Sogaella frucifera, Solenapsis geminata, Spissistilus spp., Stalk borer,
  • the methods of the invention are particularly applicable to the control of resistant insects (and resistance in insects) of the family Aphididae, such as: Acyrthosiphum pisum, Aphis citricola, Aphis craccivora, Aphis fabae, Aphis frangu-lae, Aphis glycines, Aphis gossypii, Aphis nasturtii, Aphis pomi, Aphis spiraecola, Aulacorthum solani, Brachycaudus helichrysi, Brevicoryne brassicae, Diuraphis noxia, Dysaphis devecta, Dysaphis plantaginea, Eriosoma lanigerum, Hyalopterus pruni, Li-paphis erysimi, Macrosiphum avenae, Macrosiphum euphorbiae, Macrosiphum rosae, Myzus cerasi F.,
  • the methods of the invention are particularly applicable for the control of neonicotinoid resistant insects (and the neonicotinoid resistance in such insects) of these families.
  • neonicotinoid resistant aphids include Acyrthosiphum pisum, Aphis citricola, Aphis craccivora, Aphis fabae, Aphis frangulae, Aphis glycines, Aphis gossypii, Aphis nasturtii, Aphis pomi, Aphis spiraecola, Aulacorthum solani, Brachycaudus helichrysi,
  • Nasonovia ribisnigri Pemphigus bursarius, Phorodon humuli, Rhopalosiphum insertum Wa, Rhopalosiphum Aidis Fitch, Rhopalosiphum padi L, Schizaphis graminum Rond., Sitobion avenae, Toxoptera au-rantii, Toxoptera citricola, and Phylloxera vitifoliae.
  • a resistant aphid controlled by the compound of the invention is also resistant to pyrethroid insecticides, such as Lambda-cyhalothrin.
  • the insect may be resistant to neonicotionid insecticide and/or pyrethroid insecticides.
  • the compounds of formula (I) of the present invention are particularly useful for controlling chewing-biting pests, in particular insects from the order of Lepidoptera and
  • the compounds of the present invention are particularly useful for controlling sucking or piercing insects, in particular insects from the order Diptera.
  • the insecticide resistant insect is from the order Lepidoptera, Coleoptera or Diptera.
  • the insecticide resistant insect is from the order
  • Lepidoptera is selected from Agrotis yps/lon, Agrotis segetum, Alabama argillacea, Anticarsia gemmata/is, Argyresthia conjugella, Autographa gamma, Bupalus piniarius, Cacoecia murinana, Capua reticu!ana, Cheimatobia brumata, Choristoneura fumiferana, Choristoneura occidentalis, Cirphis unipuncta, Cydia pomonella, Dendrolimus pini, Diaphania nitidalis,
  • Diatraea grandiosella Earias insulana, Elasmopalpus lignose/lus, EupoeciHa ambiguella,
  • the insecticide resistant insect is from the order Coleoptera (beetles) and is selected from Agrilus sinuatus, Agriotes Uneatus, Agriotes obscurus, Amphimallus so/stitia/is, Anisandrus dispar, Anthonomus grandis, Anthonomus pomorum, Aphthona euphoridae, Athous haemorrhoida/is, Atomaria linearis, Biastophagus piniperda, Biitophaga undata, Bruchus rufimanus, Bruchus pisorum, Bruchus ientis, Byctiscus betuiae, Cassida nebuiosa, Cerotoma trifurcata, Cetonia aurata, Ceuthorrhynchus assimi/is,
  • Ceuthorrhynchus napi Chaetocnema tibialis, Conoderus vespertinus, Crioceris asparagi, Ctenicera ssp., Diabrotica iongicornis, Diabrotica semipunctata, Diabrotica 12-punctata
  • Diabrotica speciosa Diabrotica virgifera, Epiiachna varivestis, Epitrix hirtipennis, Eutinobothrus brasiiiensis, Hyiobius abietis, Hyper a brunneipennis, Hypera postica, ips typographus, Lem a biiineata, Lema meianopus, Leptinotarsa decemiineata, Limonius caiifornicus, Lissorhoptrus oryzophiius, Meianotus communis, Meiigethes aeneus, Meioiontha hippocastani, Meioiontha meioiontha, Ouiema oryzae, Otiorrhynchus sulcatus, Otiorrhynchus ovatus, Phaedon cochieariae, Phyiiobius pyri, Phyiiotreta chrysocepha
  • the insecticide resistant insect is a potato beetle, more specifically the Colorado potato beetle.
  • the insecticide resistant insect is from the order Diptera and is selected from Aedes aegypti, Aedes aibopictus, Aedes vexans, Anastrepha ludens, Anopheles macuiipennis, Anopheles crucians, Anopheles aibimanus, Anopheles gambiae, Anopheles freeborni, Anopheles ieucosphyrus, Anopheles minimus, Anopheles
  • the insecticide resistant insect is one or more of Tuta absoluta, Pieris rapae, Trichoplusia ni, Plutella xylostella, Spodoptera littoralis, Spodoptera frugiperda, Crocidolomia pavonana, Cnaphalocerus medinalis, Sesamia inferens, Chilo suppressalis, Pyrausta furnacalis, Thermesia gemmatalis, Liriomyza sp., Leptinotarsus decemlineata, Epitrix sp., Phyllotreta cruciferae, Meligethes aeneus, Hypera brunneipennis; Nilaparvata lugens, Nephotettix virens; Acyrthosiphum pisum, Bemisia tabaci, Bemisia argentifolii, Euschistus heros,
  • Cydia pomonella Elasmopalpus lignosellus, Heliothis armigera, Heliothis virescens, Heliothis zea; Agriotes lineatus, Agriotes obscurus,, Anthonomus grandis, Diabrotica longicornis, Diabrotica semipunctata, Diabrotica 12-punctata, Diabrotica speciosa, Diabrotica virgifera, Epitrix hirtipennis, Phaedon cochlearieae, Phyllotreta striolata.
  • the insecticide resistant insect is one or more of Tuta absoluta, Pieris rapae, Trichoplusia ni, Plutella xylostella, Chilo suppressalis, Liriomyza sp., Leptinotarsus decemlineata, Epitrix sp., Phyllotreta cruciferae, Franklinella occidentalis, Bemisia tabaci, Bemisia argentifolii, Agrotis ypsilon.
  • the insecticide resistant insect is one or more of Agrotis ypsilon, Heliothis virescens, Plutella xylostella, Agriotes lineatus, Diabrotica virgifera, Hypera brunneipennis, Leptinotarsus decemlineata, Phyllotreta striolata.
  • the invention relates to a method for controlling or combating non-crop pests, which are resistant to an insecticide, comprising applying to said non-crop pests or their food supply, habitat, breeding grounds or their locus, a composition comprising at least one glutathione S-transferase (GST) inhibitor of formula (I), in a free form or an acceptable salt, stereoisomers, an isotopic form, N-oxide, a derivative or mixture thereof and the insecticide, towards which non-crop pests are resistant.
  • GST glutathione S-transferase
  • the invention further relates to the use of GST inhibitor compounds of formula (I) for the protection of non-living organic materials against non-crop pests.
  • the invention provides the method of controlling resistance to one or more insecticides in non-crop pests, which comprises alternately or simultaneously applying glutathione S-transferase (GST) inhibitor of formula (I) in a free form or an acceptable salt, stereoisomers, an isotopic form, N-oxide, a derivative or mixture thereof and the insecticide, towards which non-crop pests are resistant, to said non-crop pests or to a crop of useful plants susceptible to and/or under attack from said non-crop pests.
  • GST glutathione S-transferase
  • the invention provides the method wherein the resistant non-crop pests developed resistance against insecticides selected from avermectins, milbemycins, cyclodienes, phosphines, carbamates, pyrethroids, spinosyns, neonicotinoids, diamides, anthranilamide, beta-ketonitrile derivatives, Tetronic and Tetramic acid derivatives, nereistoxin analogues, acaricides, insect growth regulators or antifeedants.
  • insecticides selected from avermectins, milbemycins, cyclodienes, phosphines, carbamates, pyrethroids, spinosyns, neonicotinoids, diamides, anthranilamide, beta-ketonitrile derivatives, Tetronic and Tetramic acid derivatives, nereistoxin analogues, acaricides, insect growth regulators or antifeedants.
  • the non-crop pests which are resistant to an insecticide, are pests of the classes Chilopoda and Diplopoda and of the orders Isoptera, Diptera, Blattaria (Blattodea), Dermaptera, Hemiptera, Hymenoptera, Orthop- tera, Siphonaptera, Thysanura, Phthiraptera, Araneida, Parasitiformes and Acaridida.
  • the present invention provides a method for controlling or combating following non-crop pests, which are resistant to an insecticide:
  • centipedes e.g. Scutigera coleoptrata
  • spiders e.g. Latrodectus mactans, and Loxosceles reclusa
  • ticks and parasitic mites ticks (Ixodida), e.g. Ixodes scapularis, Ixodes holocyclus, Ixodes pacificus, Rhiphicephalus sanguineus, Dermacentor andersoni, Dermacentor variabilis, Amblyomma americanum, Ambryomma maculatum, Orni- thodorus hermsi, Ornithodorus turicata and parasitic mites (Mesostigmata), e.g. Orni- thonyssus bacoti and Dermanyssus gallinae,
  • cockroaches e.g. Blattella germanica, Blattella asahinae, Peri- planeta americana, Periplaneta japonica, Periplaneta brunnea, Periplaneta fuligginosa, Periplaneta australasiae, and Blatta orientalis,
  • mosquitoes e.g. Aedes aegypti, Aedes albopictus, Aedes vexans,
  • Anatrepha ludens Anopheles maculipennis, Anopheles crucians, Anopheles albimanus
  • Anopheles gambiae Anopheles freeborni, Anopheles leucosphyrus, Anopheles minimus, Anopheles quadrimaculatus, Calliphora vicina, Chrysomya bezziana, Chrysomya hominivorax, Chrysomya macellaria, Chrysops discalis, Chrysops silacea, Chrysops atlanticus, Cochliomyia hominivorax, Cordylobia anthropophaga, Culicoides furens, Culex pipiens, Culex nigripalpus, Culex quinquefasciatus, Culex tarsalis, Culiseta inor- nata, Culiseta melanura, Dermatobia hominis, Fannia canicularis, Gasterophilus intes- tinalis, Glossina morsitans, Glossina palpalis, Glossina fuscipes,
  • Earwigs e.g. forficula auricularia
  • true bugs Hemiptera
  • Cimex lectularius Cimex lectularius
  • Cimex hemipterus Reduvius senilis
  • Triatoma spp. Rhodnius prolixus
  • Arilus critatus
  • Vespula squamosa Paravespula vulgaris, Paravespula pennsylvanica, Paravespula germanica, Dolicho- vespula maculata, Vespa crabro, Polistes rubiginosa, Camponotus floridanus, and Li- nepithema humile,
  • crickets grasshoppers, locusts (Orthoptera), e.g. Acheta domestica, Gryllotalpa gryllo- talpa, Locusta migratoria, Melanoplus bivittatus, Melanoplus femurrubrum, Melanoplus mexicanus, Melanoplus sanguinipes, Melanoplus spretus, Nomadacris septemfasciata, Schistocerca americana, Schistocerca gregaria, Dociostaurus maroccanus, Tachycines asynamorus, Oedaleus senegalensis, Zonozerus variegatus, Hieroglyphus daganensis, Kraussaria angulifera, Calliptamus italicus, Cho oicetes terminifera, and Locustana pardaliria,
  • fleas e.g. Ctenocephalides felis, Ctenocephalides canis, Xenopsylla cheopis, Pulex irritans, Tunga penetrans, and Nosopsyllus fasciatus,
  • the invention provides the method of controlling non-crop pests, which are resistant to an insecticide, wherein non-crop pests are pests of the classes Chilopoda and Dilopoda and of the orders Isoptera, Diptera, Blattaria (Blattodea), Dermaptera, Hemiptera, Hymenoptera, Orthoptera, Siphonaptera, Thysanura, Phthiraptera, Araneida, Parasitiformes and Acaridida.
  • non-crop pests are pests of the classes Chilopoda and Dilopoda and of the orders Isoptera, Diptera, Blattaria (Blattodea), Dermaptera, Hemiptera, Hymenoptera, Orthoptera, Siphonaptera, Thysanura, Phthiraptera, Araneida, Parasitiformes and Acaridida.
  • the invention provides a method, which process comprises treating the non-crop insect, which are resistant to an insecticide, the plant, or the plant propagation material selected from the group consisting of seeds, roots, fruits, tubers, bulbs, rhizomes, shoots, sprouts and other parts of plants, including seedlings and young plants to be protected against non-crop pest attack, the stored materials or harvest, or alternately, the locus or soil or soil substituents or surfaces therefrom, with an effective amount of at least one glutathione S- transferase (GST) inhibitor of formula (I) or an acceptable salt, stereoisomers, an isotopic form, N-oxide, a derivative or mixture thereof and the insecticide, towards which insects are resistant.
  • GST glutathione S- transferase
  • the present invention relates to a method of controlling resistance to one or more insecticides in non-crop pests, wherein the resistant non-crop pests developed resistance against against following insecticides:
  • M.1 Acetylcholine esterase (AChE) inhibitors M.1A carbamates, e.g. aldicarb, alanycarb, bendio-carb, benfuracarb, butocarboxim, butoxycarboxim, carbaryl, carbofuran, carbosulfan, ethiofen-carb, fenobucarb, formetanate, furathiocarb, isoprocarb, methiocarb, methomyl, metolcarb, oxam-yl, pirimicarb, propoxur, thiodicarb, thiofanox, trimethacarb, XMC, xylylcarb and triazamate; or M.1 B organophosphates, e.g.
  • methamidophos methidathion, mevinphos, mono-crotophos, naled, omethoate, oxydemeton- methyl, parathion, parathion-methyl, phenthoate, phorate, phosalone, phosmet, phosphamidon, phoxim, pirimiphos- methyl, profenofos, propetamphos, prothiofos, pyraclofos, pyridaphenthion, quinalphos, sulfotep, tebupirimfos, temephos, terbufos, tetrachlorvinphos, thiometon, triazophos, trichlorfon, and vamidothion;
  • GABA-gated chloride channel antagonists M.2A cyclodiene organochlorine compounds, e.g. endosulfan or chlordane; or M.2B fiproles (phenylpyrazoles), e.g. ethiprole, fipronil, flufiprole, pyrafluprole, and pyriprole;
  • M.3 Sodium channel modulators from the class of M.3A pyrethroids e.g. acrinathrin, allethrin, d- cis-trans allethrin, d-trans allethrin, bifenthrin, bioallethrin, bioallethrin S-cylclopentenyl, bio- resmethrin, cycloprothrin, cyfluthrin, beta-cyfluthrin, cyhalothrin, lambda-cyhalothrin, gamma- cyhalothrin, cypermethrin, alpha-cypermethrin, beta-cypermethrin, theta-cypermethrin, zeta- cypermethrin, cyphenothrin, deltamethrin, empenthrin, esfenvalerate, etofen
  • M.4 Nicotinic acetylcholine receptor agonists M.4A neonicotinoids, e.g. acetamiprid, clothianidin, cycloxaprid, dinotefuran, imidacloprid, nitenpyram, thiacloprid and thiamethoxam; or the compounds M .4A.1 4,5-Dihydro-N-nitro-1 -(2-oxiranylmethyl)-1 H-imidazol-2-amine , M.4A.2: (2E-)-1 -[(6-Chloropyridin-3-yl)methyl]-N'-nitro-2-pentylidenehydrazinecarboximidamide; or M4.A.3: 1-[(6-Chloropyridin-3-yl)methyl]-7-methyl-8-nitro-5-propoxy-1 , 2, 3, 5,6,7- hexahydroimidazo[1 ,2-a]pyridine
  • M.8 miscellaneous non-specific (multi-site) inhibitors e.g. M.8A alkyl halides as methyl bromide and other alkyl halides, M.8B chloropicrin, M.8C sulfuryl fluoride, M.8D borax, or M .8E tartar emetic;
  • M.9 Chordotonal organ TRPV channel modulators e.g. M.9B pymetrozine; pyrifluquinazon;
  • M.10 Mite growth inhibitors e.g. M.10A clofentezine, hexythiazox, and diflovidazin, or M.10B etoxazole;
  • M.1 1 Microbial disruptors of insect midgut membranes, e.g. bacillus thuringiensis or bacillus sphaericus and the insecticdal proteins they produce such as bacillus thuringiensis subsp. is- raelensis, bacillus sphaericus, bacillus thuringiensis subsp. aizawai, bacillus thuringiensis subsp. kurstaki and bacillus thuringiensis subsp. tenebrionis, or the Bt crop proteins: Cry1 Ab, Cryl Ac, Cryl Fa, Cry2Ab, mCry3A, Cry3Ab, Cry3Bb, and Cry34/35Ab1 ;
  • M.12 Inhibitors of mitochondrial ATP synthase e.g. M.12A diafenthiuron, or M.12B organotin miti-cides such as azocyclotin, cyhexatin, or fenbutatin oxide, M.12C propargite, or M.12D tetrad ifon;
  • chlorfenapyr DNOC, or sulfluramid
  • Nicotinic acetylcholine receptor (nAChR) channel blockers e.g. nereistoxin analogues ben-sultap, cartap hydrochloride, thiocyclam, or thiosultap sodium;
  • M.15 Inhibitors of the chitin biosynthesis type 0, such as benzoylureas e.g. bistrifluron, chlorfluazuron, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, teflubenzuron, or triflumuron;
  • benzoylureas e.g. bistrifluron, chlorfluazuron, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, teflubenzuron, or triflumuron;
  • M.16 Inhibitors of the chitin biosynthesis type 1 e.g. buprofezin;
  • Ecdyson receptor agonists such as diacylhydrazines, e.g. methoxyfenozide, tebufenozide, halofenozide, fufenozide, or chromafenozide;
  • Octopamin receptor agonists e.g. amitraz
  • M.20 Mitochondrial complex III electron transport inhibitors e.g. M.20A hydramethylnon, M.20B acequinocyl, M.20C fluacrypyrim; or M.20D bifenazate;
  • M.21 Mitochondrial complex I electron transport inhibitors e.g. M.21A METI acaricides and insec-ticides such as fenazaquin, fenpyroximate, pyrimidifen, pyridaben, tebufenpyrad or tolfenpyrad, or M.21 B rotenone;
  • M.22 Voltage-dependent sodium channel blockers e.g. M.22A indoxacarb, M.22B
  • M.22B.1 2-[2-(4-Cyanophenyl)-1-[3-(trifluoromethyl)phenyl] _i ethylidene]-N-[4- (difluoromethoxy)phenyl]-hydrazinecarboxamide or M.22B.2: N-(3-Chloro-2-methyhphenyl)-2- [(4-chlorophenyl)[4-[methyl(methylsulfonyl)amino]phenyl]- , methylene]-hydrazinecarboxamide; M.23 Inhibitors of the of acetyl CoA carboxylase, such as Tetronic and Tetramic acid derivatives, e.g. spirodiclofen, spiromesifen, or spirotetramat; M.23.1 spiropidion
  • M.24 Mitochondrial complex IV electron transport inhibitors e.g. M.24A phosphine such as alu minium phosphide, calcium phosphide, phosphine or zinc phosphide, or M.24B cyanide;
  • M.25 Mitochondrial complex II electron transport inhibitors such as beta-ketonitrile derivatives, e.g. cyenopyrafen or cyflumetofen
  • M.28 Ryanodine receptor-modulators from the class of diamides e.g. flubendiamide, chlor- antraniliprole, cyantraniliprole, tetraniliprole, M.28.1 : (R)-3-Chlor-N 1 - ⁇ 2-methyl-4-[1 , 2,2,2 - tetrafluoro-1-(trifluoromethyl)ethyl]phenyl ⁇ -N2-(1-methyl-2-methylsulfonylethyl)phthalamid,
  • M .28.2 (S)-3-Chloro-N 1 - ⁇ 2-methyl-4-[1 ,2,2,2-tetrafluoro-1 -(trifluoromethyl)ethyl]phenyl ⁇ -N2-(1 - methyl-2-methylsulfonylethyl)phthalamid
  • M.28.3 cyclaniliprole
  • M.28.4 methyl-2-[3,5- dibromo-2-( ⁇ [3-bromo-1 -(3-chlorpyridin-2-yl)-1 H-pyrazol-5-yl]carbonyl ⁇ -'amino)benzoyl]-1 ,2- dimethylhydrazine-carboxylate; or M.28.5a) N-[4,6-dichloro-2-[(diethyl-lambda-4- sulfanylideneJ-carbamoyll-phenyll ⁇ -iS-chloro ⁇ -pyridy -S-i
  • M.29 Chordotonal organ Modulators - undefined target site, e.g. flonicamid;
  • M.UN. insecticidal active compounds of unknown or uncertain mode of action e.g. afido-'pyro- pen, afoxolaner, azadirachtin, amidoflumet, benzoximate, broflanilide, bromopropylate, chino-rnethionat, cryolite, dicloromezotiaz , dicofol, flufenerim, flometoquin, fluensulfone, fluhexafon, fluopyram, fluralaner , metoxadiazone, piperonyl butoxide, pyflu-bumide, pyridalyl, tioxazafen, M .UN .3: 1 1-(4-chloro-2,6-dimethylphenyl)-12-hydroxy- 1 ,4-dioxa-9- azadispiro[4.2.4.2]-tetradec-1 1 -en-10-one ,
  • M.UN.4 3-(4’-fluoro-2,4-dimethylbiphenyl-3-yl)-4-hydroxy-8-oxa-1-azaspiro[4.5]dec-3-en-2-one
  • M.UN.5 1-[2-fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulfinyl]phenyl]-3-(trifluoromethyl)-1 H-1 ,2,4- triazole-5-amine, or actives on basis of bacillus firmus (Votivo, 1-1582);
  • M.UN.8 fluazaindolizine ; M .UN.9. a): 4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4H-isoxazol-
  • M .UN.9.b fluxametamide
  • M.UN.10 5-[3-[2,6- dichloro-4-(3,3-dichloroallyloxy)phenoxy]propoxy]-1 H-pyrazole;
  • M.UN.1 1.f) 4-fluoro-N-[2-fluoro-3-[[[2-iodo-4-[1 ⁇ -tetrafluoro-l -itrifluoromethylJ-'ethyll-B- (trifluoromethyl)phenyl]amino]carbonyl]phenyl]-N-methyl-benzamide; M.UN.1 1.g) 3-fluoro-N-[2- fluoro-S- ⁇ -iodo ⁇ -n ⁇ -tetrafluoiO-HtrifluoiOmethy -'ethyll-e-
  • M.UN.1 1.m N-[5-[[2-bromo-6-chloro-4-[1 ,2,2,3,3,3-hexafluoro-1 -(trifluoromethyl)- propyl]phenyl]carbamoyl]-2-cyano-phenyl]-4-cyano-2-methyl-benzamide; M.UN.11.n) 4-cyano- N-[2-cyano-5-[[2,6-dichloro-4-[1 ,2,2,3,3,3-hexafluoro-1 -(trifluoromethyl)- propyl]phenyl]carbamoyl]phenyl]-2-methyl-benzamide; M.UN.1 1.o) 4-cyano-N-[2-cyano-5-[[2,6- dichloro-4-[1 ⁇ -tetrafluoro-Htrifluoromethy ethyllphenyllcarbamoyl ⁇ phenyll ⁇ -methyl- benzamide; M.UN.1 1.p) N
  • M.UN.14a 1 -[(6-Chloro-3-pyridinyl)methyl]-1 ,2,3,5,6,7-hexahydro-5-methoxy-7-methyl-8-nitro- imidazo[1 ,2-a]pyridine; or M.UN.14b) 1-[(6-Chloropyridin-3-yl)methyl]-7-methyl-8-nitro- 1 ,2,3,5,6,7-hexahydroimidazo[1 ,2-a]pyridin-5-ol;
  • M. UN.16a 1 -isopropyl-N,5-dimethyl-N-pyridazin-4-yl-pyrazole-4-carboxamide; or M. UN.16b) 1 - (1 ,2-dimethylpropyl)-N-ethyl-5-methyl-N-pyridazin-4-yl-pyrazole-4-carboxamide; M.UN.16c)
  • M.UN.16d 1 -[1 -(1-cyanocyclopropyl)ethyl]-N-ethyl-5-methyl-N-pyridazin-4-yl-pyrazole-4- carboxamide
  • M.UN.16e N-ethyl-1 -(2-fluoro-1-methyl-propyl)-5-methyl-N-pyridazin-4-yl- pyrazole-4-carboxamide
  • M .U N .16f 1 -(1 ,2-dimethylpropyl)-N ,5-dimethyl-N-pyridazin-4-yl- pyrazole-4-carboxamide
  • M .UN.16g 1 -[1-(1-cyanocyclopropyl)ethyl]-N,5-dimethyl-N-pyridazin- 4-yl-pyrazole-4-carboxamide
  • M .U N .16h N-methyl-1 -(2-fluoro
  • M. UN.17a N-(1-methylethyl)-2-(3-pyridinyl)-2H-indazole-4-carboxamide
  • M. UN.17b N- cyclopropyl-2-(3-pyridinyl)-2H-indazole-4-carboxamide
  • M. UN.18a N-[3-chloro-1 -(3-pyridyl)pyrazol-4-yl]-N-ethyl-3-(3,3,3- trifluoropropylsulfanyl)propanamide
  • M. UN.18b N-[3-chloro-1-(3-pyridyl)pyrazol-4-yl]-N-ethyl-3- (3,3,3-trifluoropropylsulfinyl)propanamide
  • M.UN .21 N-[4-Chloro-3-[[(phenylmethyl)amino]carbonyl]phenyl]-1-methyl-3-(1 ,1 ,2,2,2- pentafluoroethyl)-4-(trifluoromethyl)-1 H-pyrazole-5-carboxamide ;
  • M. UN.22a 2-(3-ethylsulfonyl- 2-pyridyl)-3-methyl-6-(trifluoromethyl)imidazo[4,5-b]pyridine, or M. UN.22b 2-[3-ethylsulfonyl-5- (trifluoromethyl)-2-pyridyl]-3-methyl-6-(trifluoromethyl)imidazo[4,5-b]pyridine ;
  • M. UN.23a 4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4H-isoxazol-3-yl]-N-[(4R)-2-ethyl-3-oxo- isoxazolidin-4-yl]-2-methyl-benzamide, or M. UN.23b 4-[5-(3,5-dichloro-4-fluoro-phenyl)-5- (trifluoromethyl)-4H-isoxazol-3-yl]-N-[(4R)-2-ethyl-3-oxo-isoxazolidin-4-yl]-2-methyl-benzamide ; M.
  • M.4 cycloxaprid is known from WO2010/069266 and WO201 1/069456.
  • M.4A.1 is known from CN 103814937; CN 105367557, CN 105481839.
  • M .4A.2, guadipyr is known from WO 2013/003977, and M.4A.3 (approved as paichongding in China) is known from WO
  • M.22B.1 is described in CN 10171577 and M .22B.2 in CN 102126994.
  • Spiropidion M.23.1 is known from WO 2014/191271.
  • M.28.1 and M.28.2 are known from W02007/101540.
  • M.28.3 is described in W02005/077934.
  • M.28.4 is described in W02007/043677.
  • M .28.5a) to M.28.5d) and M.28.5h) are described in WO 2007/006670, WO2013/024009 and WO
  • M.28.5i is described in WO2011/085575, M.28.5j) in W02008/134969, M.28.5k) in US2011/046186 and M .28.5I) in WO2012/034403.
  • M.28.6 can be found in WO2012/034472.
  • M.UN.3 is known from W02006/089633 and M.UN.4 from W02008/067911.
  • M.UN.5 is descrhbed in W02006/043635, and biological control agents on the basis of bacillus firmus are described in W02009/124707. Flupyrimin is described in WO2012/029672.
  • M.U N.8 is known from WO2013/055584.
  • M .UN .9.a is described in WO2013/050317.
  • M.UN.9.b is described in WO2014/126208.
  • M. UN.10 is known from WO2010/060379. Broflanilide and M.UN.H .b) to M.UN.1 1.h) are described in W02010/018714, and M.UN.11 i) to M.UN.1 1 .p) in WO
  • M.UN.12.a) to M.UN.12.C) are known from WO2010/006713
  • M.UN.12.d) and M.UN.12.e) are known from WO2012/000896, and M.UN.12.f) to M.UN.12.m) from WO
  • M. UN.14a) and M. UN.14b) are known from W02007/101369.
  • M.UN.16.a) to M.UN.16h) are de-scribed in WO2010/034737, WO2012/084670, and WO2012/143317, resp., and M.UN.16i) and M.UN.16j) are described in WO2015/055497.
  • M .UN .17a) to M .UN .17 ) are described in WO2015/038503.
  • M.UN.18a) to M.UN.18d) are described in US2014/0213448.
  • M.UN.19 is de-scribed in WO2014/036056.
  • M.UN.20 is known from WO2014/090918.
  • M.UN.21 is known from EP2910126.
  • M. UN.22a and M.UN.22b are known from W02015/059039 and W02015/190316.
  • M.UN.23a and M.UN.23b are known from WO2013/050302.
  • M .UN .24a and M. UN.24b are known from WO2012/126766.
  • Acynonapyr M.U N.25 is known from WO
  • Benzpyrimoxan M.UN.26 is known from W02016/104516.
  • M.UN.27 is known from WO2016174049.
  • the non-crop pest which are resistant to insecticide, is selected from flies, mosquitoes (Diptera).
  • the invention relates to the method of controlling resistance to one or more insecticides in non-crop pests, which comprises applying glutathione S-transferase (GST) inhibitor of formula (I), in free form or acceptable salt, stereoisomers, an isotopic form, N- oxide, a derivative or mixture thereof and the insecticide, towards which the non-crop pests are resistant, to said non-crop pests preferably selected from flies and mosquitoes.
  • GST glutathione S-transferase
  • the non-crop pest is selected from: Aedes aegypti, Aedes albopictus, Aedes vexans, Anas- trepha ludens, Anopheles maculipennis, Anopheles crucians, Anopheles albimanus, Anopheles gambiae, Anopheles freeborni, Anopheles leucosphyrus, Anopheles minimus, Anopheles quadrimaculatus, Calliphora vicina, Chrysomya bezziana, Chrysomya hominivorax, Chrysomya macellaria, Chrysops discalis, Chrysops silacea, Chrysops atlanticus, Cochliomyia hominivorax, Cordylobia anthropophaga, Culicoides furens, Culex pipiens, Culex nigripalpus, Culex quinquefasciatus, Culex tars
  • the non-crop pest, which are resistant to insecticide is selected from termites (Isoptera). More preferably, the non-crop pest, which are resistant to insecticide, is selected from: Calotermes flavicollis, Leucotermes flavipes, Heterotermes aureus, Reticulitermes flavipes, Reticulitermes virginicus, Reticulitermes lucifugus, Termes natalensis, and Coptotermes formosanus.
  • the invention relates to a method for controlling resistance in non-crop pest, which are resistant to insecticide, is selected from termites, which method comprises applying a GST inhibitor compound of formula (I), in free form or an acceptable salt, stereoisomers, an isotopic form, N-oxide, a derivative or mixture thereof and the insecticide, towards which insects are resistant.
  • the non-crop pest, which are resistant to insecticide is selected from ants (Hymenoptera). More preferably, the non-crop pest, which are resistant to insecticide, is selected from: Crematogaster spp., Hoplocampa minuta, Hoplocampa testudinea, Monomo urn pharaonis, Solenopsis geminata, Sole- nopsis invicta, Solenopsis richteri, Solenopsis xyloni, Pogonomyrmex barbatus, Pogo-nomyrmex californicus, Dasymutilla occidentalis, Bombus spp.
  • ants Hymenoptera
  • the non-crop pest, which are resistant to insecticide is selected from: Crematogaster spp., Hoplocampa minuta, Hoplocampa testudinea, Monomo urn pharaonis, Solenopsis geminata, Sole- nopsis invicta, Solenopsis richter
  • Vespula squamosa Paravespula vulgaris, Paravespula pennsylvanica, Paravespula germanica, Dolicho- vespula maculata, Vespa crabro, Polistes rubiginosa, Camponotus floridanus, and Linepithema humile.
  • the invention relates to a method for controlling or combating non-crop pest, which are resistant to insecticide, is selected from ants, which method comprises applying a GST inhibitor compound of formula (I) or an acceptable salt, stereoisomers, an isotopic form, a derivative or mixture thereof and the insecticide, towards which insects are resistant.
  • the non-crop pest which are resistant to insecticide, is selected from crickets, grasshoppers, locusts (Orthoptera). More preferably, the non-crop pest, which are resistant to insectide, is selected from: Acheta domestica, Gryllotalpa gryllo- talpa, Locusta migratoria, Melanoplus bivittatus, Melanoplus femurrubrum, Melanoplus mexicanus, Melanoplus sanguinipes,
  • Zonozerus variegatus Hieroglyphus daganensis, Kraussaria angulifera, Callip-tamus italicus, Chooicetes terminifera, and Locustana pardaliria.
  • the invention relates to a method for controlling or combating non-crop pest, which are resistant to insecticide, is selected from crickets, grasshoppers, locusts
  • Orthoptera which method comprises applying a GST inhibitor compound of formula (I) or an acceptable salt, stereoisomers, an isotopic form, a derivative or mixture thereof and the insecticide, towards which insects are resistant.
  • the invention relates to the method according to the invention, wherein the non-crop pest is selected from flies, mosquitoes (Diptera).
  • Netting or textile material impregnated with a compound of formula (I) or an acceptable salt, stereoisomers, an isotopic form, a derivative or mixture thereof and the insecticide, towards which insects are resistant, as defined herein.
  • Method according to the invention wherein stored products are protected from pests, especially a method according to the invention, wherein the stored product is selected from tobacco, nuts, cocoa, fruits, wood.
  • the GST inhibitor compounds of formula (I or an acceptable salt, stereoisomers, an isotopic form, a derivative or mixture thereof, and compositions comprising them are used for the protection of non-living organic materials, including but are not limited to house-hold goods such as fats, oils, mono- oligo- or
  • cellulose-containing materials e.g. wooden materials such as houses, trees, board fences, or sleepers and also paper; and also construction materials, furniture, leathers, animal, plant and synthetic fibers, vinyl articles, electric wires and cables as well as styrene foams.
  • the invention relates to use of compounds of formula (I) according to the invention, for the protection of human beings and animals against mosquitos.
  • the invention especially relates to textile materials, foils or nettings which comprise or incorporate a compound according to the invention or an acceptable salt, stereoisomers, an isotopic form, a derivative or mixture thereof and the insecticide, towards which mosquitos are resistant.
  • "incorporated” means embedded.
  • "incorporated” means comprised in impregnated form.
  • the invention also relates to above-mentioned textile material for the protection of plants or crops, e.g. tobacco, nuts, fruits, trees, wood.
  • the foils or nettings can also be used as mulch foil in the protection of crops.
  • the invention relates to a netting, which comprises use of compound of formula I.
  • the invention relates to a method for protecting humans from insects, which are resistant to insecticides, which method comprises applying a GST inhibitor compound of formula (I) or an acceptable salt, stereoisomers, an isotopic form, a derivative or mixture thereof and the insecticide, towards which non-crop insects are resistant.
  • the invention relates to a method for protecting stored goods from non crop insects, which are resistant to insecticide, whichmethod comprises applying a GST inhibitor compound of formula (I) or an acceptable salt, stereoisomers, an isotopic form, a derivative or mixture thereof and the insecticide, towards which non-crop insects are resistant.
  • the invention relates to a method for protecting stored goods which are selected from tobacco, nuts, cocoa, fruits, wood; which method comprises applying a compound of formula (I) or an acceptable salt, stereoisomers, an isotopic form, a derivative or mixture thereof and the insecticide, towards which non-crop insects are resistant.
  • the present invention also relates to a method for the protection of non-living organic materials against non-crop pests, which are resistant to insecticides, preferably against non-crop pests selected from the group consisting of
  • the class Diplopoda and of the orders Isoptera, Diptera, Blattaria (Blattodea), Dermaptera, Hemiptera, Hymenoptera, Orthoptera, and Thysanura comprising contacting the pests or their food supply, habitat, breeding grounds, their locus or the non-living organic materials them selves with at least one compound of formula (I), or an acceptable salt, stereoisomers, an isotopic form, a derivative or mixture thereof and the insecticide, towards which non-crop insects are resistant , or a composition comprising at least one compound of formula (I), or an acceptable salt, stereoisomers, an isotopic form, a derivative or mixture thereof and the insecticide, towards which non-crop insects are resistant.
  • compounds of formula (I) or an acceptable salt, stereoisomers, an isotopic form, a derivative or mixture thereof and the insecticide, towards which non-crop insects are resistant are preferably used for protecting cellulose-containing non-living organic materials:
  • compounds of formula (I) or an acceptable salt, stereoisomers, an isotopic form, a derivative or mixture thereof and the insecticide, towards which non-crop insects are resistant or a composition comprising at least one compound of formula (I), or an acceptable salt, stereoisomers, an isotopic form, a derivative or mixture thereof and the insecticide, towards which non-crop insects are resistant, are used for protecting cellulose-containing non-living organic materials against resistant non-crop pests from the Isoptera, Diptera, Blattaria
  • the present invention also provides a method for protecting cellulose-containing non-living organic materials against non-crop pests, which are resistant to insecticides, preferably from the Isoptera, Diptera, Blattaria (Blattodea), Hymenoptera, and Orthoptera orders, most preferably the Isoptera orders, comprising contacting the pests or their food supply, habitat, breeding grounds, their locus or the cellulose containing non-living organic materials themselves with at least one of a compound of formula (I) or an acceptable salt, stereoisomers, an isotopic form, a derivative or mixture thereof and the insecticide, towards which non-crop insects are resistant , or a composition comprising at least one compound of formula (I), or an acceptable salt, stereoisomers, an isotopic form, a derivative or mixture thereof and the insecticide, towards which non-crop insects are resistant.
  • insecticides preferably from the Isoptera, Diptera, Blattaria (Blattodea), Hymenoptera, and Orthoptera orders
  • the present invention also provides a method for protecting mono- oligo- or polysaccharides and proteins against non-crop pests, which are resistant to insecticides, preferably selected from the Dermaptera, Diplopoda, Isoptera, Diptera, Blattaria (Blattodea), Hymenoptera, Orthoptera and Tysanura orders, most preferably the Isoptera, Diptera, Blattaria (Blattodea), and Hymenoptra orders, comprising contacting the pests or their food supply, habitat, breeding grounds or their locus with at least one compounds of formula (I) or an acceptable salt, stereoisomers, an isotopic form, a derivative or mixture thereof and the insecticide, towards which non-crop insects are resistant , or a composition comprising at least one compound of formula (I), or an acceptable salt, stereoisomers, an isotopic form, a derivative or mixture thereof and the insecticide, towards which non-crop insects are resistant.
  • insecticides preferably selected from the Dermapter
  • compounds of formula (I) or an acceptable salt, stereoisomers, an isotopic form, a derivative or mixture thereof and the insecticide, towards which non-crop insects are resistant are preferably used for protection of animals against non crop pest, which are resistant towards insecticides, of the class Chilopoda, and of the orders Araneida, Hemiptera, Diptera, Phthiraptera, Siphonaptera, Parasitiformes and Acaridida by treatment of the pests in water bodies and / or in and around buildings, including but not limited to walls, ground, manure piles, turf grass, pastures, sewers and materials used in the construction of buildings and also mattresses and bedding.
  • compounds of formula (I) or an acceptable salt, stereoisomers, an isotopic form, a derivative or mixture thereof and the insecticide, towards which non-crop insects are resistant are used for protection of animals against resistant non-crop pest of the Diptera, Phthiraptera, Siphonaptera, and
  • Animals include warm-blooded animals, including humans and fish.
  • Compounds of formula (I) are preferably used for protection of warm-blooded animals such as cattle, sheep, swine, camels, deer, horses, poultry, rabbits, goats, dogs and cats.
  • the invention also relates to agrochemical compositions comprising an auxiliary and at least one compound of formula (I) of the present invention or a mixture thereof.
  • the compounds of formula (I) of the present invention or the mixtures thereof can be converted into customary types of agro-chemical compositions, e. g. solutions, emulsions, suspensions, dusts, powders, pastes, granules, pressings, capsules, and mixtures thereof.
  • agro-chemical compositions e. g. solutions, emulsions, suspensions, dusts, powders, pastes, granules, pressings, capsules, and mixtures thereof.
  • composi-tion types are suspensions (e.g. SC, OD, FS), emulsifiable concentrates (e.g. EC), emulsions (e.g. EW, EO, ES, ME), capsules (e.g. CS, ZC), pastes, pastilles, wettable powders or dusts (e.g. WP, SP, WS, DP, DS), pressings (e.g.
  • compositions types are defined in the“Catalogue of pesticide formulation types and international coding system”, Technical Mono-graph No. 2, 6th Ed. May 2008, CropLife International.
  • compositions are prepared in a known manner, such as described by Mollet and Grube- mann, Formulation technology, Wiley VCH, Weinheim, 2001 ; or Knowles, New developments in crop protection product formulation, Agrow Reports DS243, T&F Informa, London, 2005.
  • auxiliaries are solvents, liquid carriers, solid carriers or fillers, surfac-tants, dispersants, emulsifiers, wetters, adjuvants, solubilizers, penetration enhancers, protec-tive colloids, adhesion agents, thickeners, humectants, repellents, attractants, feeding stimu-lants, compatibilizers, bactericides, anti-freezing agents, anti-foaming agents, colorants, tackifiers and binders.
  • Suitable solvents and liquid carriers are water and organic solvents, such as mineral oil frac tions of medium to high boiling point, e.g. kerosene, diesel oil; oils of vegetable or animal origin; aliphatic, cyclic and aromatic hydrocarbons, e. g. toluene, paraffin, tetrahydronaphthalene, al kylated naphthalenes; alcohols, e.g. ethanol, propanol, butanol, benzylalcohol, cyclo-'hexanol; glycols; DMSO; ketones, e.g. cyclohexanone; esters, e.g.
  • mineral oil frac tions of medium to high boiling point e.g. kerosene, diesel oil
  • oils of vegetable or animal origin oils of vegetable or animal origin
  • aliphatic, cyclic and aromatic hydrocarbons e. g. toluene, paraffin, tetrahydronaphthal
  • lactates carbonates, fatty acid esters, gamma-butyrolactone; fatty acids; phosphonates; amines; amides, e.g. N-methylpyrrolidone, fatty acid dimethylamides; and mixtures thereof.
  • Suitable solid carriers or fillers are mineral earths, e.g. silicates, silica gels, talc, kaolins, lime stone, lime, chalk, clays, dolomite, diatomaceous earth, bentonite, calcium sulfate, magnesium sulfate, magnesium oxide; polysaccharide powders, e.g. cellulose, starch; fertilizers, e.g. am- monium sulfate, ammonium phosphate, ammonium nitrate, ureas; products of vegetable origin, e.g. cereal meal, tree bark meal, wood meal, nutshell meal, and mixtures thereof.
  • mineral earths e.g. silicates, silica gels, talc, kaolins, lime stone, lime, chalk, clays, dolomite, diatomaceous earth, bentonite, calcium sulfate, magnesium sulfate, magnesium oxide
  • polysaccharide powders e.g. cellulose,
  • Suitable surfactants are surface-active compounds, such as anionic, cationic, nonionic and amphoteric surfactants, block polymers, polyelectrolytes, and mixtures thereof. Such surfactants can be used as emusifier, dispersant, solubilizer, wetter, penetration enhancer, protective colloid, or adjuvant. Examples of surfactants are listed in McCutcheon’s, Vol.1 : Emulsifiers & Detergents, McCutcheon’s Directories, Glen Rock, USA, 2008 (International Ed. or North American Ed.).
  • Suitable anionic surfactants are alkali, alkaline earth or ammonium salts of sulfonates, sul-fates, phosphates, carboxylates, and mixtures thereof.
  • sulfonates are alkylaryl- sulfonates, diphenylsulfonates, alpha-olefin sulfonates, lignine sulfonates, sulfonates of fatty acids and oils, sulfonates of ethoxylated alkylphenols, sulfonates of alkoxylated arylphenols, sulfonates of condensed naphthalenes, sulfonates of dodecyl- and tridecylbenzenes, sulfonates of naphthalenes and alkyhnaphthalenes, sulfosuccinates or sulfosuccinamates.
  • sulfates are sulfates of fatty acids and oils, of ethoxylated alkylphenols, of alcohols, of ethox ylated alcohols, or of fatty acid esters.
  • phosphates are phosphate esters. Exam ples of carboxylates are alkyl carboxylates, and carboxylated alcohol or alkylphenol eth oxy I ates.
  • Suitable nonionic surfactants are alkoxylates, N-subsituted fatty acid amides, amine oxides, esters, sugar-based surfactants, polymeric surfactants, and mixtures thereof.
  • alkoxylates are compounds such as alcohols, alkylphenols, amines, amides, arylphenols, fatty acids or fatty acid esters which have been alkoxylated with 1 to 50 equivalents.
  • Ethylene oxide and/or propylene oxide may be employed for the alkoxylation, preferably ethylene oxide.
  • Exam ples of N-subsititued fatty acid amides are fatty acid glucamides or fatty acid alkanolamides.
  • esters are fatty acid esters, glycerol esters or monoglycerides.
  • sugar- based surfactants are sorbitans, ethoxylated sorbitans, sucrose and glucose esters or alkylpolyglucosides.
  • polymeric surfactants are homo- or copolymers of
  • Suitable cationic surfactants are quaternary surfactants, for example quaternary ammonium compounds with one or two hydrophobic groups, or salts of long-chain primary amines.
  • Suitable amphoteric surfactants are alkylbetains and imidazolines.
  • Suitable block polymers are block polymers of the A-B or A-B-A type comprising blocks of polyethylene oxide and polypropylene oxide, or of the A-B-C type comprising alkanol, polyethylene oxide and polypropylene oxide.
  • Suitable polyelectrolytes are polyacids or polybases. Examples of polyacids are alkali salts of polyacrylic acid or polyacid comb polymers. Examples of polybases are polyvinylamines or polyethyleneamines.
  • Suitable adjuvants are compounds, which have a neglectable or even no pesticidal activity themselves, and which improve the biological performance of the compounds of the present invention on the target.
  • examples are surfactants, mineral or vegetable oils, and other auxilaries. Further examples are listed by Knowles, Adjuvants and additives, Agrow Reports DS256, T&F Informa UK, 2006, chapter 5.
  • Suitable thickeners are polysaccharides (e.g. xanthan gum, carboxymethylcellulose), anorgan-ic clays (organically modified or unmodified), polycarboxylates, and silicates.
  • Suitable bactericides are bronopol and isothiazolinone derivatives such as alkylisothiazoli-nones and benzisothiazolinones.
  • Suitable anti-freezing agents are ethylene glycol, propylene glycol, urea and glycerin.
  • Suitable anti-foaming agents are silicones, long chain alcohols, and salts of fatty acids.
  • Suitable colorants are pigments of low water solubility and water- soluble dyes.
  • examples are inorganic colorants (e.g. iron oxide, titan oxide, iron hexacyanofer- rate) and organic colorants (e.g. alizarin-, azo- and phthalocyanine colorants).
  • Suitable tackifiers or binders are polyvinylpyrrolidons, polyvinylacetates, polyvinyl alcohols, polyacrylates, biological or synthetic waxes, and cellulose ethers.
  • the present invention relates to the agrochemical compositions comprising at least one GST inhibitor compound of formula (I) may be combined/mixed with the pre prepared formulation of an active ingredient, for example, insecticide.
  • the present invention relates to the agrochemical compositions comprising at least one GST inhibitor compound of formula (I) and pre-prepared formulation of at least one insecticide.
  • the present invention provides the agrochemical compositions comprising at least one GST inhibitor compound of formula (I) and at least one active ingredient, for example, insecticide.
  • oils, wetters, adjuvants, fertilizer, or micronutrients, and other pesticides may be added to the active substances or the compositions comprising them as premix or, if appropriate not until immedi ately prior to use (tank mix).
  • pesticides e.g. herbicides, insecticides, fungicides, growth regulators, safeners
  • These agents can be admixed with the compositions according to the invention in a weight ratio of 1 :100 to 100:1 , preferably 1 : 10 to 10:1 .
  • composition types and their preparation are:
  • a compound of formula (I) and 5-15 wt% wetting agent e.g. alcohol alkoxylates
  • a water-soluble solvent e.g. alcohols
  • a compound of formula (I) and 1-10 wt% dispersant e. g. polyvi-nylpyrrolidone
  • a compound of formula (I) and 1-10 wt% dispersant e. g. polyvi-nylpyrrolidone
  • organic solvent e.g. cyclohexanone
  • dodecylbenzenesulfonate and castor oil ethoxylate are dissolved in 20-40 wt% water-insoluble organic solvent (e.g. aromatic hydrocarbon). This mixture is introduced into up to 100 wt% water by means of an emulsifying machine and made into a homogeneous emulsion. Dilution with water gives an emulsion.
  • water-insoluble organic solvent e.g. aromatic hydrocarbon
  • dispersants and wetting agents e.g. sodium lignosulfonate and alcohol ethoxylate
  • 0,1-2 wt% thickener e.g. xanthan gum
  • up to 100 wt% water to give a fine active substance suspension. Dilution with water gives a stable suspension of the active substances.
  • binder e.g. polyvinylalcohol
  • 50-80 wt% of a compound of formula (I) are ground finely with addition of up to 100 wt% dispersants and wetting agents (e.g. sodium lignosulfonate and alcohol ethoxylate) and prepared as water-dispersible or water-soluble granules by means of technical appliances (e. g. extrusion, spray tower, fluidized bed). Dilution with water gives a stable dispersion or solution of the active substances.
  • dispersants and wetting agents e.g. sodium lignosulfonate and alcohol ethoxylate
  • wt% of a compound of formula (I) are ground in a rotor-stator mill with addition of 1 -5 wt% dispersants (e.g. sodium lignosulfonate), 1-3 wt% wetting agents (e.g. alcohol ethoxylate) and up to 100 wt% solid carrier, e.g. silica gel. Dilution with water gives a stable dispersion or solution of the active substances.
  • dispersants e.g. sodium lignosulfonate
  • wetting agents e.g. alcohol ethoxylate
  • solid carrier e.g. silica gel
  • dispersants e.g. sodium lignosulfonate
  • 1-5 wt% thickener e.g. car- boxymethylcellulose
  • up to 100 wt% water to give a fine suspension of the active sub stance. Dilution with water gives a stable suspension of the active substances.
  • wt% of a compound of formula (I) are added to 5-30 wt% organic solvent blend (e.g. fatty acid dimethylamide and cyclohexanone), 10-25 wt% surfactant blend (e.g. alko-hol ethoxylate and arylphenol ethoxylate), and water up to 100 %. This mixture is stirred for 1 h to produce spontaneously a thermodynamically stable microemulsion.
  • organic solvent blend e.g. fatty acid dimethylamide and cyclohexanone
  • surfactant blend e.g. alko-hol ethoxylate and arylphenol ethoxylate
  • An oil phase comprising 5-50 wt% of a compound of formula (I), 0-40 wt% water insoluble organic solvent (e.g. aromatic hydrocarbon), 2-15 wt% acrylic monomers (e.g.
  • methylmethacrylate, methacrylic acid and a di- or triacrylate are dispersed into an aqueous solution of a protective colloid (e.g. polyvinyl alcohol). Radical polymerization initiated by a radi cal initiator results in the formation of poly(meth)acrylate microcapsules.
  • a protective colloid e.g. polyvinyl alcohol.
  • Radical polymerization initiated by a radi cal initiator results in the formation of poly(meth)acrylate microcapsules.
  • an oil phase comprising 5-50 wt% of a compound of formula (I) and optionally active compound selected from insecticide and/or herbicide, 0-40 wt% water insoluble organic solvent (e.g.
  • 1-10 wt% of a compound of formula (I) are ground finely and mixed intimately with up to 100 wt% solid carrier, e.g. finely divided kaolin.
  • 0.5-30 wt% of a compound of formula (I) is ground finely and associated with up to 100 wt% solid carrier (e.g. silicate). Granulation is achieved by extrusion, spray-drying or the fluidized bed.
  • solid carrier e.g. silicate
  • a compound of formula (I) 1-50 wt% are dissolved in up to 100 wt% organic solvent, e.g. aromatic hydrocarbon.
  • compositions types i) to xi) may optionally comprise further auxiliaries, such as 0.1 -1 wt% bactericides, 5-15 wt% anti-freezing agents, 0.1-1 wt% anti-foaming agents, and 0.1 -1 wt% col orants.
  • auxiliaries such as 0.1 -1 wt% bactericides, 5-15 wt% anti-freezing agents, 0.1-1 wt% anti-foaming agents, and 0.1 -1 wt% col orants.
  • the agrochemical compositions generally comprise between 0.01 and 95%, preferably be tween 0.1 and 90%, and most preferably between 0.5 and 75%, by weight of active substances.
  • the active substances are employed in a purity of from 90% to 100%, preferably from 95% to 100% (according to NMR spectrum).
  • composition according to the invention usually from a predosage device, a knapsack sprayer, a spray tank, a spray plane, or an irrigation system.
  • a predosage device usually from a knapsack sprayer, a spray tank, a spray plane, or an irrigation system.
  • agrochemical composition is made up with water, buffer, and/or further auxiliaries to the desired application concentration and the ready-to-use spray liquor or the agrochemical composition according to the invention is thus obtained.
  • 20 to 2000 liters, preferably 50 to 400 liters, of the ready-to-use spray liquor are applied per hectare of agricultural useful area.
  • composition according to the in vention such as parts of a kit or parts of a binary or ternary mixture may be mixed by the user himself in a spray tank and further auxiliaries may be added, if appropriate.
  • either individual components of the composition according to the invention or partially premixed components may be mixed by the user in a spray tank and further auxiliaries and additives may be added, if appropriate.
  • either individual components of the composition according to the in vention or partially premixed components e. g. components comprising compounds of the pre sent invention and/or mixing partners as defined above, can be applied jointly (e.g. after tank mix) or consecutively.
  • the application of the the compounds of formula (I) of the present invention, or an acceptable salt, an isotopic form, a derivative or mixture thereof, is preferably as explained in the following.
  • the animal pest also referred to as "invertebrate pest"
  • insect pest i.e. the insects, arachnids and nematodes
  • contacting includes both direct contact (applying the compounds/compositions directly on the animal pest and indirect contact (applying the compounds/compositions to the locus of the animal pest).
  • the compounds of the present invention are employed in form of compositions by treating the insects’ surfaces, materials or rooms to be protected from insecticidal attack with an insecticidally effective amount of the insecticide towards which insects are resistant.
  • the application can be carried out both before and after the infection of the surfaces, materials or rooms by the insects.
  • the present invention also includes a method of combating or controlling animal pests which comprises contacting the animal pests, which are resistant towards insecticides, their habitat, breeding ground, food supply, area, material or environment in which the animal pests are growing or may grow, or the materials, surfaces or spaces to be protected from animal attack or infestation with at least one compound of formula (I) or an acceptable salt, stereoisomers, an isotopic form, a derivative or mixture thereof and the insecticide, towards which animal pests are resistant.
  • animal pests may be controlled by contacting the target pest, its food supply, habitat, breeding ground or its locus with an effective amount of compounds of formula (I) or an acceptable salt, stereoisomers, an isotopic form, a derivative or mixture thereof and the insecticide, towards which target pests are resistant.
  • the application may be carried out before or after the infection of the locus by the pest.
  • the compounds of formula (I) of the invention or an acceptable salt, stereoisomers, an isotopic form, a derivative or mixture thereof and the insecticide, towards which non-crop insects are resistant, can also be applied preventively to places at which occurrence of the resistant pests are expected.
  • “Locus” means a habitat, breeding ground, area, material or environment in which a pest or parasite is growing or may grow.
  • the quantity of active ingredient ranges from 0.0001 to 500 g per 100 m2, preferably from 0.001 to 20 g per 100 m2.
  • Customary application rates in the protection of materials are, for example, from 0.01 g to 1000 g of active compounds per m 2 treated material, desirably from 0.1 g to 50 g per m2 .
  • the compositions for use in the impregnation of materials typically contain from 0.001 to 95 weight %, preferably from 0.1 to 45 weight %, and more preferably from 1 to 25 weight % of at least one compound of formula (I) of the invention or an acceptable salt, stereoisomers, an isotopic form, a derivative or mixture thereof and the insecticide, towards which pests are resistant.
  • the compounds of formula (I) are effective through both contact (via glass, wall, bed net, carpet, plant parts or animal parts), and ingestion (bait, or plant part).
  • compounds of formula (I) or an acceptable salt, stereoisomers, an isotopic form, a derivative or mixture thereof and the insecticide, towards which pests are resistant are preferably used in a bait composition.
  • the bait can be a liquid, a solid or a semisolid preparation (e.g. a gel).
  • Solid baits can be formed into various shapes and forms suitable to the respective application e.g. granules, blocks, sticks, disks.
  • Liquid baits can be filled into various devices to ensure proper application, e.g. open containers, spray devices, droplet sources, or evaporation sources.
  • Gels can be based on aqueous or oily matrices and can be formulated to particular necessities in terms of stickyness, moisture retention or aging characteristics.
  • the bait employed in the composition is a product, which is sufficiently attractive to incite insects such as ants, termites, wasps, flies, mosquitos, crickets etc. or cockroaches to eat it.
  • Food stimu'ants are chosen, for example, but not exclusively, from animal and/or plant proteins (meat-, fish- or blood meal, insect parts, egg yolk), from fats and oils of animal and/or plant origin, or mono-, oligo- or polyorganosaccharides, especially from sucrose, lactose, fructose, dextrose, glucose, starch, pectin or even molasses or honey.
  • Fresh or decaying parts of fruits, crops, plants, animals, insects or specific parts thereof can also serve as a feeding stimulant.
  • Sex pheromones are known to be more insect specific. Specific pheromones are described in the literature and are known to those skilled in the art.
  • the typical content of at least one compound of formula (I) of the invention or an acceptable salt, stereoisomers, an isotopic form, a derivative or mixture thereof and the insecticide, towards which pests are resistant is from 0.001 weight % to 15 weight %, desirably from 0.001 weight % to 5%.
  • At least one compound of formula (I) of the invention or an acceptable salt, stereoisomers, an isotopic form, a derivative or mixture thereof, are present in the formulation form of an aerosol.
  • Formulations of compounds of formula (I) or an acceptable salt, stereoisomers, an isotopic form, a derivative or mixture thereof and the insecticide, towards which pests are resistant are highly suitable for the professional and non-professional user for controlling pests, which are resistant towards insecticide, such as flies, fleas, ticks, mosquitos or cockroaches.
  • Aerosol recipes are preferably composed of the active compounds, solvents such as lower alcohols (e.g. methanol, ethanol, propanol, butanol), ketones (e.g. acetone, methyl ethyl ketone), paraffin hydrocarbons (e.g.
  • kerosenes having boiling ranges of approximately 50 to 250°C, dimethylformamide, N-methylpyrrolidone, dimethyl sulfoxide, aromatic hydrocarbons such as toluene, xylene, water, furthermore auxiliaries such as emulsifiers such as sorbitol monooleate, oleyl ethoxylate having 3-7 mol of ethylene oxide, fatty alcohol ethoxylate, perfume oils such as ethereal oils, esters of medium fatty acids with lower alcohols, aromatic carbonyl compounds, if appropriate stabilizers such as sodium benzoate, amphoteric surfactants, lower epoxides, triethyl orthoformate and, if required, propel'ants such as propane, butane, nitrogen, compressed air, dimethyl ether, carbon dioxide, nitrous oxide, or mixtures of these gases.
  • auxiliaries such as emulsifiers such as sorbitol monooleate, oleyl ethoxylate having 3-7
  • the oil spray formulations differ from the aerosol recipes in that no propellants are used.
  • the content of active ingredients is from 0.001 to 80 weights %, preferably from 0.01 to 50 weight% and most preferably from 0.01 to 15 weight %.
  • the compounds of formula (I) and its respective compositions can also be used in mosquito and fumigating coils, smoke cartridges, vaporizer plates or long-term vaporizers and also in moth papers, moth pads or other heat-independent vaporizer systems.
  • the methods to control infectious diseases transmitted by insects e.g. malaria, dengue and yellow fever, lymphatic filariasis, and leishmaniasis
  • insects e.g. malaria, dengue and yellow fever, lymphatic filariasis, and leishmaniasis
  • compounds of formula (I) or an acceptable salt, stereoisomers, an isotopic form, a derivative or mixture thereof and the insecticide, towards which insects are resistant and its respective compositions also comprise treating surfaces of huts and houses, air spraying and impregnation of curtains, tents, clothing items, bed nets, tsetse-fly trap or the like.
  • compositions for application to fibers, fabric, knitgoods, nonwovens, netting material or foils and tarpaulins preferably comprise at least one compound of formula (I) or an acceptable salt, stereoisomers, an isotopic form, a derivative or mixture thereof and the insecticide, towards which insects are resistant , optionally a repellent and at least one binder.
  • Suitable repellents for example are N, N-Diethyl-meta- toluamide (DEET), N,Ndiethylphenylacetamide (DEPA), 1-(3-cyclohexan-1-yl-carbonyl)-2- methylpiperine, (2-hydroxymethylcyclohexyl) acetic acid lactone, 2-ethyl-l ,3-hexandiol, indalone, Methylneodecanamide (MN DA), a pyrethroid not used for insect control such as ⁇ (+/- )-3-allyl-2-methyl-4-oxocyclopent-2-(+)-enyl-(+)-trans-chrysantemate (Esbiothrin), a repellent derived from or identical with plant extracts like limonene, eugenol, (+)-Eucamalol (1), (-)-1 -epi- eucamalol or crude plant extracts from plants like Eu
  • Suitable binders are selected for example from polymers and copolymers of vinyl esters of aliphatic acids (such as such as vinyl acetate and vinyl versatate), acrylic and methacrylic esters of alcohols, such as butyl acrylate, 2-ethylhexylacrylate, and methyl acrylate, mono- and di-ethylenically unsaturated hydrocarbons, such as styrene, and aliphatic diens, such as butadiene.
  • the impregnation of curtains and bednets is done in general by dipping the textile material into emulsions or dispersions of the insecticide or spraying them onto the nets.
  • the compounds of formula (I) and its compositions can be used for protecting wooden materials such as trees, board fences, sleepers, etc. and buildings such as houses, outhouses, factories, but also construction materials, furniture, leathers, fibers, vinyl articles, electric wires and cables etc. from ants and/or termites, which are resistant to insecticide, and for controlling ants and termites from doing harm to crops or human being (e.g. when the pests invade into houses and public facilities).
  • the compounds of formula (I) or an acceptable salt, stereoisomers, an isotopic form, a derivative or mixture thereof and the insecticide, towards which insects are resistant are applied not only to the surrounding soil surface or into the under-floor soil in order to protect wooden materials but it can also be applied to lumbered articles such as surfaces of the under floor concrete, alcove posts, beams, plywoods, furniture, etc., wooden articles such as particle boards, half boards, etc. and vinyl articles such as coated electric wires, vinyl sheets, heat insulating material such as styrene foams, etc.
  • the ant controller of the present invention is applied to the crops or the surrounding soil, or is directly applied to the nest of ants or the like.
  • a method of controlling undesired vegetation which are resistant to a herbicide, which method comprises applying to said herbicide resistant undesired vegetation a composition comprising at least one glutathione S- transferase (GST) inhibitor of formula (I) in free form or or an acceptable salt, stereoisomers, an isotopic form, N-oxide, a derivative or mixture thereof and the herbicide, towards which undesired vegetation is resistant.
  • GST glutathione S- transferase
  • a method of protecting a crop of useful plants susceptible to and/or under attack by undesired vegetation, which are resistant to a herbicide comprises applying to said crop, treating a plant propagation material of said crop with, and/or applying to said undesired vegetation, a composition comprising at least one glutathione S-transferase (GST) inhibitor of formula (I) in free form or an acceptable salt, stereoisomers, an isotopic form, N-oxide, a derivative or mixture thereof and the herbicide, towards which undesired vegetation is resistant.
  • GST glutathione S-transferase
  • a method of controlling resistance to one or more herbicides in undesired vegetation which comprises alternately or simultaneously applying glutathione S-transferase (GST) inhibitor of formula (I) in free form or an acceptable salt, stereoisomers, an isotopic form, N-oxide, a derivative or mixture thereof, and the herbicide, towards which the undesired vegetation are resistant, to said undesired vegetation or to a crop of useful plants susceptible to and/or under attack from said undesired vegetation.
  • GST glutathione S-transferase
  • a method of controlling undesired vegetation which are resistant to a herbicide, which method comprises treating the undesired vegetation, the plant, or the plant propagation material selected from the group consisting of seeds, roots, fruits, tubers, bulbs, rhizomes, shoots, sprouts and other parts of plants, including seedlings and young plants to be protected against undesired vegetation attack, the stored materials or harvest, or alternately, the locus or soil or soil substituents or surfaces therefrom, with an effective amount of at least one glutathione S-transferase (GST) inhibitor of formula (I) ) in free form or an acceptable salt, stereoisomers, an isotopic form, N-oxide, a derivative or mixture thereof and at least one herbicide towards which the undesired vegetation are resistant.
  • GST glutathione S-transferase
  • the resistant undesired vegetation developed resistance against herbicide selected from the following list of herbicides
  • ALS inhibitors acetolactate synthase inhibitors
  • EBP inhibitors enolpyruvyl shikimate 3-phosphate synthase inhibitors
  • DHP inhibitors 7,8-dihydropteroate synthase inhibitors
  • VLCFA inhibitors inhibitors of the synthesis of very long chain fatty acids
  • herbicides selected from the group consisting of bromobutide, chlorflurenol, chlorflurenol-methyl, cinmethylin, cumyluron, dalapon, dazomet, difenzoquat, difenzoquat- metilsulfate, dimethipin, DSMA, dymron, endothal and its salts, etobenzanid, flamprop, flamprop-isopropyl, flamprop-methyl, flamprop-M-isopropyl, flamprop-M-methyl, flurenol, flurenol-butyl, flurprimidol, fosamine, fosamine-ammonium, indanofan, indaziflam, maleic hydrazide, mefluidide, metam, methiozolin (CAS 403640-27-7), methyl azide, methyl bromide, methyl-dymron, methyl iodide, MSMA,
  • herbicidal compounds B and/or the safeners C as described herein are capable of forming geometrical isomers, for example E/Z isomers, it is possible to use both, the pure isomers and mixtures thereof, in the compositions according to the invention.
  • the herbicidal compounds B and/or the safeners C as described herein have one or more centers of chirality and, as a consequence, are present as enantiomers or diastereomers, it is possible to use both, the pure enantiomers and diastereomers and their mixtures, in the compositions according to the invention.
  • the herbicidal compounds B and/or the safeners C as described herein have ionizable functional groups, they can also be employed in the form of their agriculturally acceptable salts. Suitable are, in general, the salts of those cations and the acid addition salts of those acids whose cations and anions, respectively, have no adverse effect on the activity of the active compounds.
  • the herbicide to which the undesired vegetation is resistant is from the following list of herbicides: b1 ) from the group of the lipid biosynthesis inhibitors:
  • ACC-herbicides such as alloxydim, alloxydim-sodium, butroxydim, clethodim, clodinafop, clodinafop-propargyl, cycloxydim, cyhalofop, cyhalofop-butyl, diclofop, diclofop-methyl, fenoxaprop, fenoxaprop-ethyl, fenoxaprop-P, fenoxaprop-P-ethyl, fluazifop, fluazifop-butyl, fluazifop-P, fluazifop-P-butyl, haloxyfop, haloxyfop-methyl, haloxyfop-P, haloxyfop-P-methyl, metamifop, pinoxaden, profoxydim, propaquizafop, quizalofop, quizalofop-ethy
  • ACC herbicides such as benfuresate, butylate, cycloate, dalapon, dimepiperate, EPTC, esprocarb, ethofumesate, flupropanate, molinate, orbencarb, pebulate, prosulfocarb, TCA, thiobencarb, tiocarbazil, triallate and vernolate;
  • sulfonylureas such as amidosulfuron, azimsulfuron, bensulfuron, bensulfuron-methyl, chlorimuron, chlorimuron-ethyl, chlorsulfuron, cinosulfuron, cyclosulfamuron, ethametsulfuron, ethametsulfuron-methyl, ethoxysulfuron, flazasulfuron, flucetosulfuron, flupyrsulfuron, flupyrsulfuron-methyl-sodium, foramsulfuron, halosulfuron, halosulfuron-methyl, imazosulfuron, iodosulfuron, iodosulfuron-methyl-sodium, iofensulfuron, iofensulfuron-sodium, mesosulfuron, metazosulfuron, metsulfuron, metsulfuron-methyl, nicos
  • imidazolinones such as imazamethabenz, imazamethabenz-methyl, imazamox, imazapic, imazapyr, imazaquin and imazethapyr, triazolopyrimidine herbicides and sulfonanilides such as cloransulam, cloransulam-methyl, diclosulam, flumetsulam, florasulam, metosulam,
  • penoxsulam pyrimisulfan and pyroxsulam
  • pyhmidinylbenzoates such as bispyribac, bispyribac-sodium, pyribenzoxim, pyriftalid, pyhminobac, pyriminobac-methyl, pyrithiobac, pyrithiobac-sodium, 4-[[[2-[(4,6-dimethoxy-2- pyrimidinyl)oxy]phenyl]methyl]amino]-benzoic acid-1 -methylethyl ester (CAS 420138-41 -6), 4- [[[2-[(4,6-dimethoxy-2-pyrimidinyl)oxy]phenyl]methyl]amino]-benzoic acid propyl ester (CAS 420138-40-5), N-(4-bromophenyl)-2-[(4,6-dimethoxy-2-pyrimidinyl)oxy]benzenemethanamine (CAS 420138-01 -8),
  • sulfonylaminocarbonyl-triazolinone herbicides such as flucarbazone, flucarbazone-sodium, propoxycarbazone, propoxycarbazone-sodium, thiencarbazone and thiencarbazone-methyl; and triafamone;
  • compositions comprising at least one imidazolinone herbicide
  • inhibitors of the photosystem II e.g. 1-(6-tert-butylpyrimidin-4-yl)-2-hydroxy-4- methoxy-3-methyl-2H-pyrrol-5-one (CAS 1654744-66-7), 1-(5-tert-butylisoxazol-3-yl)-2-hydroxy- 4-methoxy-3-methyl-2H-pyrrol-5-one (CAS 1637455-12-9), 1-(5-tert-butylisoxazol-3-yl)-4-chloro- 2-hydroxy-3-methyl-2H-pyrrol-5-one (CAS 1637453-94-1 ), 1 -(5-tert-butyl-1-methyl-pyrazol-3-yl)- 4-chloro-2-hydroxy-3-methyl-2H-pyrrol-5-one (CAS 1654057-29-0), 1 -(5-tert-butyl-1-methyl- pyrazol-3-yl)-3-chloro-2-hydroxy-4-methyl-2H-pyrrol-5-one (CAS
  • a preferred embodiment of the invention relates to those compositions comprising at least one aryl urea herbicide. Among these, likewise a preferred embodiment of the invention relates to those compositions comprising at least one triazine herbicide. Among these, likewise a preferred embodiment of the invention relates to those compositions comprising at least one nitrile herbicide;
  • acifluorfen acifluorfen-sodium, azafenidin, bencarbazone, benzfendizone, bifenox, butafenacil, carfentrazone, carfentrazone-ethyl, chlomethoxyfen, chlorphthalim, cinidon-ethyl, fluazolate, flufenpyr, flufenpyr-ethyl, flumiclorac, flumiclorac-pentyl, flumioxazin, fluoroglycofen, fluoroglycofen-ethyl, fluthiacet, fluthiacet-methyl, fomesafen, halosafen, lactofen, oxadiargyl, oxadiazon, oxyfluorfen, pentoxazone, profluazol, pyraclonil, pyraflufen, pyraflufen-ethyl, saflufenacil, sulf
  • PDS inhibitors beflubutamid, diflufenican, fluridone, flurochloridone, flurtamone, norflurazon, picolinafen, and 4-(3-trifluoromethylphenoxy)-2-(4-trifluoromethylphenyl)pyrimidine (CAS 180608-33-7), HPPD inhibitors: benzobicyclon, benzofenap, bicyclopyrone, clomazone, fenquinotrione, isoxaflutole, mesotrione, oxotrione (CAS 1486617-21-3), pyrasulfotole, pyrazolynate, pyrazoxyfen, sulcotrione, tefuryltrione, tembotrione, tolpyralate, topramezone , bleacher, unknown target: aclonifen, amitrole flumeturon,2-chloro-3-methylsulfanyl-N-(1- methyltetrazol-5-y
  • glyphosate glyphosate, glyphosate-isopropylammonium, glyposate-potassium and glyphosate-trimesium (sulfosate);
  • bilanaphos (bialaphos), bilanaphos-sodium, glufosinate, glufosinate-P and glufosinate- ammonium;
  • compounds of group K1 dinitroanilines such as benfluralin, butralin, dinitramine, ethalfluralin, fluchloralin, oryzalin, pendimethalin, prodiamine and trifluralin, phosphoramidates such as amiprophos, amiprophos-methyl, and butamiphos, benzoic acid herbicides such as chlorthal, chlorthal-dimethyl, pyridines such as dithiopyr and thiazopyr, benzamides such as propyzamide and tebutam; compounds of group K2: carbetamide, chlorpropham, flamprop, flamprop- isopropyl, flamprop-methyl, flamprop-M-isopropyl, flamprop-M-methyl and propham ; among these, compounds of group K1 , in particular dinitroanilines are preferred;
  • chloroacetamides such as acetochlor, alachlor, amidochlor, butachlor, dimethachlor, dimethenamid, dimethenamid-P, metazachlor, metolachlor, metolachlor-S, pethoxamid, pretilachlor, propachlor, propisochlor and thenylchlor, oxyacetanilides such as flufenacet and mefenacet, acetanilides such as diphenamid, naproanilide, napropamide and napropamide-M , tetrazolinones such fentrazamide, and other herbicides such as anilofos, cafenstrole, fenoxasulfone, ipfencarbazone, piperophos, pyroxasulfone and isoxazoline compounds of the formulae 11.1 , I I.2, II .3, I I.4, II .5, II.6, I I.7, II.8 and
  • the isoxazoline compounds of the formula (II) are known in the art, e.g. from WO 2006/024820, WO 2006/037945, WO 2007/071900 and WO 2007/096576; among the VLCFA inhibitors, preference is given to chloroacetamides and oxyacetamides; b1 1 ) from the group of the cellulose biosynthesis inhibitors:
  • 2,4-D and its salts and esters such as clacyfos, 2,4-DB and its salts and esters,
  • aminocyclopyrachlor and its salts and esters aminopyralid and its salts such as aminopyralid- dimethylammonium, aminopyralid-tris(2-hydroxypropyl)ammonium and its esters, benazolin, benazolin-ethyl, chloramben and its salts and esters, clomeprop, clopyralid and its salts and esters, dicamba and its salts and esters, dichlorprop and its salts and esters, dichlorprop-P and its salts and esters, flopyrauxifen, fluroxypyr, fluroxypyr-butometyl, fluroxypyr-meptyl, halauxifen and its salts and esters (CAS 943832-60-8; MCPA and its salts and esters, MCPA-thioethyl, MCPB and its salts and esters, mecoprop and its salts and esters, mecoprop-P and its salts and esters, picloram and its salt
  • Preferred cations are the ions of the alkali metals, preferably of lithium, sodium and potassium, of the alkaline earth metals, preferably of calcium and magnesium, and of the transition metals, preferably of manganese, copper, zinc and iron, further ammonium and substituted ammonium in which one to four hydrogen atoms are replaced by Ci-C4-alkyl, hydroxy-Ci-C4-alkyl, C1-C4- alkoxy-Ci-C 4 -alkyl, hydroxy-Ci-C 4 -alkoxy-Ci-C 4 -alkyl, phenyl or benzyl, preferably ammonium, methylammonium, isopropylammonium, dimethylammonium, diethylammonium,
  • diisopropylammonium trimethylammonium, triethylammonium, tris(isopropyl)ammonium, heptylammonium, dodecylammonium, tetradecylammonium, tetramethylammonium, tetraethylammonium, tetrabutylammonium, 2-hydroxyethylammonium (olamine salt), 2-(2- hydroxyeth-1-oxy)eth-1-ylammonium (diglycolamine salt), di(2-hydroxyeth-1 -yl)ammonium (diolamine salt), tris(2-hydroxyethyl)ammonium (trolamine salt), tris(2- hydroxypropyl)ammonium, benzylthmethylammonium, benzyltriethylammonium, N,N,N- trimethylethanolammonium (choline salt), furthermore phosphonium ions, sulfonium ions, preferably
  • Herbicidal compounds B and/or safeners C as described herein having a carboxyl group can be employed in the form of the acid, in the form of an agriculturally suitable salt as mentioned above or else in the form of an agriculturally acceptable derivative, for example as amides, such as mono- and di-Ci-C 6 -alkylamides or arylamides, as esters, for example as allyl esters, propargyl esters, Ci-Cio-alkyl esters, alkoxyalkyl esters, tefuryl ((tetrahydrofuran-2-yl)methyl) esters and also as thioesters, for example as Ci-Ci 0 -alkylthio esters.
  • amides such as mono- and di-Ci-C 6 -alkylamides or arylamides
  • esters for example as allyl esters, propargyl esters, Ci-Cio-alkyl esters, alkoxyalkyl est
  • Preferred mono- and di- Ci-C 6 -alkylamides are the methyl and the dimethylamides.
  • Preferred arylamides are, for example, the anilides and the 2-chloroanilides.
  • Preferred alkyl esters are, for example, the methyl, ethyl, propyl, isopropyl, butyl, isobutyl, pentyl, mexyl (1-methylhexyl), meptyl (1- methylheptyl), heptyl, octyl or isooctyl (2-ethyl hexyl) esters.
  • Ci-C4-alkoxy-Ci-C 4 -alkyl esters are the straight-chain or branched Ci-C 4 -alkoxy ethyl esters, for example the 2- methoxyethyl, 2-ethoxyethyl, 2-butoxyethyl (butotyl), 2-butoxypropyl or 3-butoxypropyl ester.
  • An example of a straight-chain or branched Ci-Cio-alkylthio ester is the ethylthio ester.
  • the compositions contain at least one glutathione S-transferase (GST) inhibitor of formula (I) in free form or an acceptable salt, stereoisomers, an isotopic form, N-oxide, a derivative or mixture thereof and at least one inhibitor of the lipid biosynthesis (herbicide b1 ).
  • GST glutathione S-transferase
  • These are compounds that inhibit lipid biosynthesis. Inhibition of the lipid biosynthesis can be affected either through inhibition of acetylCoA carboxylase (hereinafter termed ACC herbicides) or through a different mode of action (hereinafter termed non-ACC herbicides).
  • ACC herbicides belong to the group A of the HRAC classification system whereas the non-ACC herbicides belong to the group N of the HRAC classification.
  • compositions contain at least one glutathione S-transferase (GST) inhibitor of formula (I) in free form or an acceptable salt, stereoisomers, an isotopic form, N-oxide, a derivative or mixture thereof and at least one ALS inhibitor (herbicide b2).
  • GST glutathione S-transferase
  • the herbicidal activity of these compounds is based on the inhibition of acetolactate synthase and thus on the inhibition of the branched chain amino acid biosynthesis.
  • These inhibitors belong to the group B of the HRAC classification system.
  • herbicidal activity of these compounds is based either on the inhibition of the photosystem II in plants (so-called PSII inhibitors, groups C1 , C2 and C3 of HRAC classification) or on diverting the electron transfer in photosystem I in plants (so-called PSI inhibitors, group D of HRAC classification) and thus on an inhibition of photosynthesis.
  • PSII inhibitors are preferred.
  • compositions contain at least one glutathione S- transferase (GST) inhibitor of formula (I) in free form or an acceptable salt, stereoisomers, an isotopic form, N-oxide, a derivative or mixture thereof and at least one bleacher-herbicide (herbicide b5).
  • GST glutathione S- transferase
  • the herbicidal activity of these compounds is based on the inhibition of the carotenoid biosynthesis.
  • PDS inhibitors compounds which inhibit carotenoid biosynthesis by inhibition of phytoene desaturase
  • HPPD inhibitors compounds that inhibit the 4-hydroxyphenyhpyruvate-dioxygenase
  • DOXsynthase group F4 of H RAC class
  • compounds which inhibit carotenoid biosynthesis by an unknown mode of action bleacher - unknown target, group F3 of HRAC classification.
  • compositions contain at least one glutathione S- transferase (GST) inhibitor of formula (I) in free form or an acceptable salt, stereoisomers, an isotopic form, N-oxide, a derivative or mixture thereof and at least one mitosis inhibitor
  • GST glutathione S- transferase
  • herbicide b9 The herbicidal activity of these compounds is based on the disturbance or inhibition of microtubule formation or organization, and thus on the inhibition of mitosis.
  • These inhibitors belong to the groups K1 and K2 of the HRAC classification system. Among these, compounds of the group K1 , in particular dinitroanilines, are preferred.
  • compositions according to the present invention comprising at least one herbicide B selected from herbicides of class b1 , b2, b3, b5 and b9.
  • compositions according to the present invention which comprise at least one herbicide B selected from the herbicides of class b1 , b2 and b5.
  • compositions according to the present invention comprise at least one GST inhibitor compound of formula (I) and at least one safener C.
  • Safeners are chemical compounds which prevent or reduce damage on useful plants without having a major impact on the herbicidal action of the herbicidal active components of the present compositions towards unwanted plants. They can be applied either before sowings (e.g. on seed treatments, shoots or seedlings) or in the pre-emergence application or post emergence application of the useful plant.
  • the safeners and the at least one glutathione S- transferase (GST) inhibitor of formula (I) in free form or an acceptable salt, stereoisomers, an isotopic form, N-oxide, a derivative or mixture thereof and/or the herbicides B can be applied simultaneously or in succession.
  • Suitable safeners are e.g. (quinolin-8-oxy)acetic acids, 1 -phenyl-5-haloalkyl-1 H-1 ,2,4-triazol-3- carboxylic acids, 1 -phenyl-4, 5-dihydro-5-alkyl-1 H-pyrazol-3,5-dicarboxylic acids, 4,5-dihydro- 5,5-diaryl-3-isoxazol carboxylic acids, dichloroacetamides, alpha-oximinophenylacetonitriles, acetophenonoximes, 4,6-dihalo-2-phenylpyrimidines, N-[[4-(aminocarbonyl)phenyl]sulfonyl]-2- benzoic amides, 1 ,8-naphthalic anhydride, 2-halo-4-(haloalkyl)-5-thiazol carboxylic acids, phosphorthiolates and N-alkyl-O-phenylcarbamates
  • the active compounds B of groups b1 ) to b15) and the active compounds C are known herbicides and safeners, see, for example, The Compendium of Pesticide Common Names (http://www.alanwood.net/pesticides/); Farm Chemicals Flandbook 2000 volume 86, Meister Publishing Company, 2000; B. Hock, C. Fedtke, R. R. Schmidt, Herbizide [Herbicides], Georg Thieme Verlag, Stuttgart 1995; W. H. Ahrens, Herbicide Handbook, 7th edition, Weed Science Society of America, 1994; and K. K. Hatzios, Herbicide Handbook, Supplement for the 7th edition, Weed Science Society of America, 1998.
  • the assignment of the active compounds to the respective mechanisms of action is based on current knowledge. If several mechanisms of action apply to one active compound, this substance was only assigned to one mechanism of action.
  • Active compounds B and C having a carboxyl group can be employed in the form of the acid, in the form of an agriculturally suitable salt as mentioned above or else in the form of an agriculturally acceptable derivative in the compositions according to the invention.
  • suitable salts include those, where the counterion is an agriculturally acceptable cation.
  • suitable salts of dicamba are dicamba-sodium, dicamba- potassium, dicamba-methylammonium, dicamba-dimethylammonium, dicamba- isopropylammonium, dicamba-diglycolamine, dicamba-olamine, dicamba-diolamine, dicamba- trolamine, dicamba-N,N-bis-(3-aminopropyl)methylamine and dicamba-diethylenetriamine.
  • a suitable ester are dicamba-methyl and dicamba-butotyl.
  • Suitable salts of 2,4-D are 2,4-D-ammonium, 2,4-D-dimethylammonium, 2,4-D- diethylammonium, 2,4-D-diethanolammonium (2,4-D-diolamine), 2,4-D-triethanolammonium, 2,4-D-isopropylammonium, 2,4-D-triisopropanolammonium, 2,4-D-heptylammonium, 2,4-D- dodecylammonium, 2,4-D-tetradecylammonium, 2,4-D-triethylammonium, 2,4-D-tris(2- hydroxypropyl)ammonium, 2,4-D-tris(isopropyl)ammonium, 2,4-D-trolamine, 2,4-D-lithium, 2,4- D-sodium.
  • esters of 2,4-D are 2,4-D-butotyl, 2,4-D-2-butoxypropyl, 2,4-D- 3-butoxypropyl, 2,4-D-butyl, 2,4-D-ethyl, 2,4-D-ethylhexyl, 2,4-D-isobutyl, 2,4-D-isooctyl, 2,4-D- isopropyl, 2,4-D-meptyl, 2,4-D-methyl, 2,4-D-octyl, 2,4-D-pentyl, 2,4-D-propyl, 2,4-D-tefuryl and clacyfos.
  • Suitable salts of 2,4-DB are for example 2,4-DB-sodium, 2,4-DB-potassium and 2,4-DB- dimethylammonium.
  • Suitable esters of 2,4-DB are for example 2,4-DB-butyl and 2,4-DB-isoctyl.
  • Suitable salts of dichlorprop are for example dichlorprop-sodium, dichlorprop-potassium and dichlorprop-dimethylammonium. Examples of suitable esters of dichlorprop are dichlorprop- butotyl and dichlorprop-isoctyl.
  • Suitable salts and esters of MCPA include MCPA-butotyl, MCPA-butyl, MCPA-dimethyl- ammonium, MCPA-diolamine, MCPA-ethyl, MCPA-thioethyl, MCPA-2-ethylhexyl, MCPA- isobutyl, MCPA-isoctyl, MCPA-isopropyl, MCPA-isopropylammonium, MCPA-methyl, MCPA- olamine, MCPA-potassium, MCPA-sodium and MCPA-trolamine.
  • a suitable salt of MCPB is MCPB sodium.
  • a suitable ester of MCPB is MCPB-ethyl.
  • Suitable salts of clopyralid are clopyralid-potassium, clopyralid-olamine and clopyralid-tris-(2- hydroxypropyl)ammonium.
  • Example of suitable esters of clopyralid is clopyralid-methyl.
  • Examples of a suitable ester of fluroxypyr are fluroxypyr-meptyl and fluroxypyr-2-butoxy-1- methylethyl, wherein fluroxypyr-meptyl is preferred.
  • Suitable salts of picloram are picloram-dimethylammonium, picloram-potassium, picloram- triisopropanolammonium, picloram-triisopropylammonium and picloram-trolamine.
  • a suitable ester of picloram is picloram-isoctyl.
  • a suitable salt of triclopyr is triclopyr-triethylammonium.
  • Suitable esters of triclopyr are for example triclopyr-ethyl and tri cl opyr-butotyl .
  • Suitable salts and esters of chloramben include chloramben-ammonium, chloramben-diolamine, chloramben-methyl, chloramben-methylammonium and chloramben-sodium.
  • Suitable salts and esters of 2,3,6-TBA include 2,3,6-TBA-dimethylammonium, 2,3,6-TBA-lithium, 2,3,6-TBA- potassium and 2,3,6-TBA-sodium.
  • Suitable salts and esters of aminopyralid include aminopyralid-potassium, aminopyralid- dimethylammonium, and aminopyralid-tris(2-hydroxypropyl)ammonium.
  • Suitable salts of glyphosate are for example glyphosate-ammonium, glyphosate-diammonium, glyphoste-dimethylammonium, glyphosate-isopropylammonium, glyphosate-potassium, glyphosate-sodium, glyphosate-trimesium as well as the ethanolamine and diethanolamine salts, preferably glyphosate-diammonium, glyphosate-isopropylammonium and glyphosate- trimesium (sulfosate).
  • a suitable salt of glufosinate is for example glufosinate-ammonium.
  • a suitable salt of glufosinate-P is for example glufosinate-P-ammonium.
  • Suitable salts and esters of bromoxynil are for example bromoxynil-butyrate, bromoxynil- heptanoate, bromoxynil-octanoate, bromoxynil-potassium and bromoxynil-sodium.
  • Suitable salts and esters of ioxonil are for example ioxonil-octanoate, ioxonil-potassium and ioxonil-sodium.
  • Suitable salts and esters of mecoprop include mecoprop-butotyl, mecoprop-dimethylammonium, mecoprop-diolamine, mecoprop-ethadyl, mecoprop-2-ethylhexyl, mecoprop-isoctyl, mecoprop- methyl, mecoprop-potassium, mecoprop-sodium and mecoprop-trolamine.
  • Suitable salts of mecoprop-P are for example mecoprop-P-butotyl, mecoprop-P- dimethylammonium, mecoprop-P-2-ethylhexyl, mecoprop-P-isobutyl, mecoprop-P-potassium and mecoprop-P-sodium.
  • a suitable salt of diflufenzopyr is for example diflufenzopyr-sodium.
  • a suitable salt of naptalam is for example naptalam-sodium.
  • Suitable salts and esters of aminocyclopyrachlor are for example aminocyclopyrachlor- dimethylammonium, aminocyclopyrachlor-methyl, aminocyclopyrachlor- triisopropanolammonium, aminocyclopyrachlor-sodium and aminocyclopyrachlor-potassium.
  • a suitable salt of quinclorac is for example quinclorac-dimethylammonium.
  • a suitable salt of quinmerac is for example quinmerac-dimethylammonium.
  • a suitable salt of imazamox is for example imazamox-ammonium.
  • Suitable salts of imazapic are for example imazapic-ammonium and imazapic- isopropylammonium.
  • Suitable salts of imazapyr are for example imazapyr-ammonium and imazapyr- isopropylammonium.
  • a suitable salt of imazaquin is for example imazaquin-ammonium.
  • Suitable salts of imazethapyr are for example imazethapyr-ammonium and imazethapyr- isopropylammonium.
  • a suitable salt of topramezone is for example topramezone-sodium.
  • the composition comprises as component I at least one, preferably exactly one GST inhibitor compound of formula (I), and as component II at least one, preferably exactly one, herbicide B.
  • the composition comprises as component I at least one, preferably exactly one GST inhibitor compound of formula (I), and as component II at least two, preferably exactly two, herbicides B different from each other.
  • compositions comprising one or more, for example 1 , 2 or 3, GST inhibitor compounds of the formula (I) and either one or more, for example 1 , 2 or 3, herbicides B or one or more safeners C.
  • ternary compositions includes compositions comprising one or more, for example 1 , 2 or 3, GST inhibitor compounds of the formula (I), one or more, for example 1 , 2 or 3, herbicides B and one or more, for example 1 , 2 or 3, safeners C.
  • the weight ratio of the active compounds l:B is generally in the range of from 1 :1000 to 1000:1 , preferably in the range of from 1 :500 to 500:1 , in particular in the range of from 1 :250 to 250:1 and particularly preferably in the range of from 1 :75 to 75:1.
  • the weight ratio of the active compounds l:C is generally in the range of from 1 :1000 to 1000:1 , preferably in the range of from 1 :500 to 500:1 , in particular in the range of from 1 :250 to 250:1 and particularly preferably in the range of from 1 :75 to 75:1.
  • the relative proportions by weight of the components l:B are generally in the range of from 1 :1000 to 1000:1 , preferably in the range of from 1 :500 to 500:1 , in particular in the range of from 1 :250 to 250:1 and particularly preferably in the range of from 1 :75 to 75:1
  • the weight ratio of the components l:C is generally in the range of from 1 :1000 to 1000:1 , preferably in the range of from 1 :500 to 500:1 , in particular in the range of from 1 :250 to 250:1 and particularly preferably in the range of from 1 :75 to 75:1
  • the weight ratio of the components B:C is generally in the range of from 1 :1000 to 1000:1 , preferably in the range of from 1 :500 to 500:1 , in particular in the range of from 1 :250 to 250:1 and
  • the weight ratio of components I + B to component C is preferably in the range of from 1 :500 to 500:1 , in particular in the range of from 1 :250 to 250:1 and particularly preferably in the range of from 1 :75 to 75:1.
  • Particularly preferred herbicides B are the herbicides B as defined above; in particular the herbicides B.1 - B.202 listed below in table B:
  • the safeners C which, as component C, are constituent of the composition according to the invention are the safeners C as defined above; in particular the safeners C.1 - C.17 listed below in table C:
  • compositions 1.1 to 1.3671 comprising the at least one GST inhibitor compound of formula (I) and the substance(s) as defined in the respective row of table 1 :
  • Table 1 compositions 1.1 to 1.3671 :
  • weight ratios of the individual components in the preferred mixtures mentioned below are within the limits given above, in particular within the preferred limits.
  • compositions according to the invention are suitable as herbicides. They are suitable as such or as an appropriately formulated composition (agrochemical composition).
  • compositions according to the invention control vegetation on non-crop areas very efficiently, especially at high rates of application. They act against broad-leafed weeds and grass weeds in crops such as wheat, rice, corn, soybeans and cotton without causing any significant damage to the crop plants. This effect is mainly observed at low rates of application.
  • compositions according to the invention are applied to the plants mainly by spraying the leaves.
  • the application can be carried out using, for example, water as carrier by customary spraying techniques using spray liquor amounts of from about 100 to 1000 l/ha (for example from 300 to 400 l/ha).
  • the herbicidal compositions may also be applied by the low-volume or the ultra- low-volume method, or in the form of microgranules.
  • herbicidal compositions according to the present invention can be done before, during and/or after, preferably during and/or after, the emergence of the undesirable plants.
  • the herbicidal compositions according to the present invention can be applied pre- or post emergence or together with the seed of a crop plant. It is also possible to apply the compounds and compositions by applying seed, pretreated with a composition of the invention, of a crop plant. If the active compounds (I) and B and, if appropriate C, are less well tolerated by certain crop plants, application techniques may be used in which the herbicidal compositions are sprayed, with the aid of the spraying equipment, in such a way that as far as possible they do not come into contact with the leaves of the sensitive crop plants, while the active compounds reach the leaves of undesirable plants growing underneath, or the bare soil surface (post-directed, lay-by).
  • the composition according to the invention can be applied by treating seed.
  • the treatment of seed comprises essentially all procedures familiar to the person skilled in the art (seed dressing, seed coating, seed dusting, seed soaking, seed film coating, seed multilayer coating, seed encrusting, seed dripping and seed pelleting) based on the compounds of the formula (I) according to the invention or the compositions prepared therefrom.
  • the herbicidal compositions can be applied diluted or undiluted.
  • seed comprises seed of all types, such as, for example, corns, seeds, fruits, tubers, seedlings and similar forms.
  • seed describes corns and seeds.
  • the seed used can be seed of the useful plants mentioned above, but also the seed of transgenic plants or plants obtained by customary breeding methods.
  • Also of interest is the miscibility with mineral salt solutions which are employed for treating nutritional and trace element deficiencies. Non-phytotoxic oils and oil concentrates can also be added.
  • the compound of formula (I) and B and, if appropriate, C without formulation auxiliaries are, depending on the kind of effect desired, from 0.001 to 2 kg per ha, preferably from 0.005 to 2 kg per ha, more preferably from 0.05 to 0.9 kg per ha and in particular from 0.1 to 0.75 kg per ha.
  • the application rate of the compound of formula (I) and B and, if appropriate, C is from 0.001 to 3 kg/ha, preferably from 0.005 to 2.5 kg/ha and in particular from 0.01 to 2 kg/ha of active substance (a.s.).
  • the rates of application of the compound of formula (I) according to the present invention are from 0.1 g/ha to 3000 g/ha, preferably 10 g/ha to 1000 g/ha, depending on the control target, the season, the target plants and the growth stage.
  • the application rates of the compound of formula (I) are in the range from 0.1 g/ha to 5000 g/ha and preferably in the range from 1 g/ha to 2500 g/ha or from 5 g/ha to 2000 g/ha.
  • the application rate of the compound of formula (I) is 0.1 to 1000 g/ha, preferably 1 to 750 g/ha, more preferably 5 to 500 g/ha.
  • herbicidal compounds B are generally in the range of from
  • the required application rates of safeners C are generally in the range of from 0.0005 kg/ha to 2.5 kg/ha and preferably in the range of from 0.005 kg/ha to 2 kg/ha or 0.01 kg/ha to 1.5 kg/h of a.s.
  • amounts of active substance of from 0.1 to 1000 g, preferably from 1 to 1000 g, more preferably from 1 to 100 g and most preferably from 5 to 100 g, per 100 kilogram of plant propagation material (preferably seeds) are generally required.
  • the amounts of active substances applied i.e. compound of formula (I) and B and, if appropriate, C are generally employed in amounts of from 0.001 to 10 kg per 100 kg of seed.
  • the amount of the compound of formula (I) applied depends on the kind of application area and on the desired effect. Amounts customarily applied in the protection of materials are 0.001 g to 2 kg, preferably 0.005 g to 1 kg, of the compound of formula (l)per cubic meter of treated material.
  • the compound of formula (I) and the herbicide compound B and/or the herbicide safener compound C are applied in a time frame that allows simultaneous action of the active ingredients on the plants, preferably within a time-frame of at most 14 days, in particular at most 7 days.
  • compositions according to the invention can additionally be employed in a further number of crop plants for eliminating undesirable plants.
  • Preferred crops are Arachis hypogaea, Beta vulgaris spec altissima, Brassica napus var. napus, Brassica oleracea, Citrus limon, Citrus sinensis, Coffea arabica (Coffea canephora, Coffea liberica), Cynodon dactylon, Glycine max, Gossypium hirsutum, (Gossypium arboreum, Gossypium herbaceum, Gossypium vitifolium), Helianthus annuus, Hordeum vulgare, Juglans regia, Lens culinaris, Linum usitatissimum, Lycopersicon lycopersicum, Malus spec., Medicago sativa,
  • Nicotiana tabacum (N.rustica), Olea europaea, Oryza sativa , Phaseolus lunatus, Phaseolus vulgaris, Pistacia vera, Pisum sativum, Prunus dulcis, Saccharum officinarum, Secale cereale, Solanum tuberosum, Sorghum bicolor (s. vulgare), Triticale, Triticum aestivum, Triticum durum, Vicia faba, Vitis vinifera and Zea mays Especially preferred crops are crops of cereals, corn, soybeans, rice, oilseed rape, cotton, potatoes, peanuts or permanent crops.
  • compositions according to the invention can also be used in crops which have been modified by mutagenesis or genetic engineering in order to provide a new trait to a plant or to modify an already present trait.
  • crops as used herein includes also (crop) plants which have been modified by mutagenesis or genetic engineering in order to provide a new trait to a plant or to modify an already present trait.
  • Mutagenesis includes techniques of random mutagenesis using X-rays or mutagenic chemicals, but also techniques of targeted mutagenesis, in order to create mutations at a specific locus of a plant genome.
  • Targeted mutagenesis techniques frequently use oligonucleotides or proteins like
  • CRISPR/Cas CRISPR/Cas, zinc-finger nucleases, TALENs or meganucleases to achieve the targeting effect.
  • Genetic engineering usually uses recombinant DNA techniques to create modifications in a plant genome which under natural circumstances cannot readily be obtained by cross breeding, mutagenesis or natural recombination.
  • one or more genes are integrated into the genome of a plant in order to add a trait or improve a trait. These integrated genes are also referred to as transgenes in the art, while plant comprising such transgenes are referred to as transgenic plants.
  • the process of plant transformation usually produces several transformation events, wich differ in the genomic locus in which a transgene has been integrated.
  • Plants comprising a specific transgene on a specific genomic locus are usually described as comprising a specific“event”, which is referred to by a specific event name.
  • Traits which have been introduced in plants or hae been modified include in particular herbicide tolerance, insect resistance, increased yield and tolerance to abiotic conditions, like drought.
  • Herbicide tolerance has been created by using mutagenesis as well as using genetic engineering. Plants which have been rendered tolerant to acetolactate synthase (ALS) inhibitor herbicides by conventional methods of mutagenesis and breeding comprise plant varieties commercially available under the name Clearfield ® . However, most of the herbicide tolerance traits have been created via the use of transgenes.
  • ALS acetolactate synthase
  • Herbicide tolerance has been created to glyphosate, glufosinate, 2,4-D, dicamba, oxynil herbicides, like bromoxynil and ioxynil, sulfonylurea herbicides, ALS inhibitor herbicides and 4- hydroxyphenylpyruvate dioxygenase (HPPD) inhibitors, like isoxaflutole and mesotrione.
  • HPPD 4- hydroxyphenylpyruvate dioxygenase
  • Transgenes wich have been used to provide herbicide tolerance traits comprise: for tolerance to glyphosate: cp4 epsps, epsps grg23ace5, mepsps, 2mepsps, gat4601 , gat4621 and goxv247, for tolerance to glufosinate: pat and bar, for tolerance to 2,4-D: aad-1 and aad-12, for tolerance to dicamba: dmo, for tolerance to oxynil herbicies: bxn, for tolerance to sulfonylurea herbicides: zm- hra, csr1-2, gm-hra, S4-HrA, for tolerance to ALS inhibitor herbicides: csr1-2, for tolerance to HPPD inhibitor herbicides: hppdPF, W336 and avhppd-03.
  • Transgenic com events comprising herbicide tolerance genes are for example, but not excluding others, DAS40278, MON801 , MON802, MON809, MON810, MON832, MON87411 , MON87419, MON87427, MON88017, MON89034, NK603, GA21 , MZHGOJG, HCEM485, VCO-01981 -5, 676, 678, 680, 33121 , 41 14, 59122, 98140, Bt10, Bt176, CBH-351 , DBT418, DLL25, MS3, MS6, MZIR098, T25, TC1507 and TC6275.
  • Transgenic soybean events comprising herbicide tolerance genes are for example, but not excluding others, GTS 40-3-2, MON87705, MON87708, MON87712, MON87769, MON89788, A2704-12, A2704-21 , A5547-127, A5547-35, DP356043, DAS44406-6, DAS68416-4, DAS-81419- 2, GU262, SYHT0H2, W62, W98, FG72 and CV127.
  • Transgenic cotton events comprising herbicide tolerance genes are for example, but not excluding others, 19-51 a, 31707, 42317, 81910, 281-24-236, 3006-210-23, BXN10211 , BXN 10215,
  • Transgenic canola events comprising herbicide tolerance genes are for example, but not excluding others, MON88302, HCR-1 , HCN 10, HCN28, HCN92, MS1 , MS8, PHY14, PHY23, PHY35, PHY36, RF1 , RF2 and RF3.
  • Insect resistance has mainly been created by transferring bacterial genes for insecticidal proteins to plants.
  • Transgenes which have most frequently been used are toxin genes of Bacillus spec and synthetic variants thereof, like cry1A, crylAb, cry1Ab-Ac, crylAc, cry1A.105, cry1 F, cry1 Fa2, cry2Ab2, cry2Ae, mcry3A, ecry3.1Ab, cry3Bb1 , cry34Ab1 , cry35Ab1 , cry9C, vip3A(a), vip3Aa20.
  • genes of plant origin have been transferred to other plants.
  • genes coding for protease inhibitors like CpTI and pinll.
  • a further approach uses transgenes in order to produce double stranded RNA in plants to target and downregulate insect genes.
  • An example for such a transgene is dvsnf7.
  • Transgenic corn events comprising genes for insecticidal proteins or double stranded RNA are for example, but not excluding others, Bt10, Bt11 , Bt176, MON801 , MON802, MON809, MON810, MON863, MON87411 , MON88017, MON89034, 33121 , 41 14, 5307, 59122, TC1507, TC6275, CBH-351 , MIR162, DBT418 and MZIR098.
  • Transgenic soybean events comprising genes for insecticidal proteins are for example, but not excluding others, MON87701 , MON87751 and DAS-81419.
  • Transgenic cotton events comprising genes for insecticidal proteins are for example, but not excluding others, SGK321 , MON531 , MON757, MON1076, MON15985, 31707, 31803, 31807, 31808, 42317, BNLA-601 , Eventl , COT67B, COT102, T303-3, T304-40, GFM Cry1A, GK12, MLS 9124, 281 -24-236, 3006-210-23, GHB1 19 and SGK321. Increased yield has been created by increasing ear biomass using the transgene athb17, being present in corn event MON87403, or by enhancing photosynthesis using the transgene bbx32, being present in the soybean event MON87712.
  • Crops comprising a modified oil content have been created by using the transgenes: gm-fad2-1 , Pj.D6D, Nc.Fad3, fad2-1A and fatb1 -A. Soybean events comprising at least one of these genes are: 260-05, MON87705 and MON87769.
  • Tolerance to abiotic conditions, in particular to tolerance to drought, has been created by using the transgene cspB, comprised by the corn event MON87460 and by using the transgene Hahb-4, comprised by soybean event IND-00410-5.
  • Traits are frequently combined by combining genes in a transformation event or by combining different events during the breeding process.
  • Preferred combination of traits are herbicide tolerance to different groups of herbicides, insect tolerance to different kind of insects, in particular tolerance to lepidopteran and coleopteran insects, herbicide tolerance with one or several types of insect resistance, herbicide tolerance with increased yield as well as a combination of herbicide tolerance and tolerance to abiotic conditions.
  • compositions according to the invention on crops may result in effects which are specific to a crop comprising a certain gene or event. These effects might involve changes in growth behavior or changed resistance to biotic or abiotic stress factors. Such effects may in particular comprise enhanced yield, enhanced resistance or tolerance to insects, nematodes, fungal, bacterial, mycoplasma, viral or viroid pathogens as well as early vigour, early or delayed ripening, cold or heat tolerance as well as changed amino acid or fatty acid spectrum or content.
  • compositions according to the invention are also suitable for the defoliation and/or desiccation of plant parts, for which crop plants such as cotton, potato, oilseed rape, sunflower, soybean or field beans, in particular cotton, are suitable.
  • compositions have been found for the desiccation and/or defoliation of plants, processes for preparing these compositions, and methods for desiccating and/or defoliating plants using the compositions according to the invention.
  • compositions according to the invention are suitable in particular for desiccating the above-ground parts of crop plants such as potato, oilseed rape, sunflower and soybean, but also cereals. This makes possible the fully mechanical harvesting of these important crop plants.
  • the present invention also relates to a mixture of at least one compound of formula (I) of the present invention with at least one mixing partner as defined herein after.
  • Preferred are binary mixtures of at least one compound of formula (I) of the present invention as component I with one mixing partner as defined herein after as component II.
  • Preferred weight ratios for such binary mixtures are from 5000:1 to 1 :5000, preferably from 1000:1 to 1 :1000, more preferably from 100:1 to 1 :100, particularly preferably from 10:1 to 1 :10.
  • components I and II may be used in equal amounts, or an excess of component I, or an excess of component II may be used.
  • Mixing partners can be selected from pesticides, in particular insecticides, nematicides, acaricides, fungicides, herbicides, plant growth regulators, fertilizers, and the like.
  • Preferred mixing component II partners are insecticides, nematicides, herbicides and fungicides.
  • the following list of pesticides (component II) e. g. insecticides, nematicides, herbicides, fungicides and biopesticides
  • insecticides, nematicides, herbicides, fungicides and biopesticides in conjunction with which the compounds of formula (I) can be used, is intended to illustrate the possible combinations but does not limit them:
  • Inhibitors of complex III at Q 0 site azoxystrobin (A.1.1), coumethoxystrobin (A.1.2), coumoxystrobin (A.1.3), dimoxystrobin (A.1.4), enestroburin (A.1.5), fenaminstrobin (A.1.6), fenoxystrobin/flufenoxystrobin (A.1.7), fluoxastrobin (A.1.8), kresoxim-methyl (A.1.9), mandestrobin (A.1.10), metominostrobin (A.1.11), orysastrobin (A.1.12), picoxystrobin (A.1.13), pyraclostrobin (A.1.14), pyrametostrobin (A.1.15), pyraoxystrobin (A.1.16), trifloxystrobin (A.1.17), 2-(2-(3-(2,6-dichlorophenyl)-1-methyl-allylideneaminooxymethyl)-phenyl)- 2-methoxyi
  • respiration inhibitors diflumetorim (A.4.1); nitrophenyl derivates: binapacryl (A.4.2),
  • fentin salts e. g. fentin-acetate (A.4.8), fentin chloride (A.4.9) or fentin hydroxide (A.4.10); ametoctradin (A.4.1 1); silthiofam (A.4.12);
  • - C14 demethylase inhibitors triazoles: azaconazole (B.1.1), bitertanol (B.1.2), bromuconazole (B.1.3), cyproconazole (B.1.4), difenoconazole (B.1.5), diniconazole (B.1.6), diniconazole-M (B.1.7), epoxiconazole (B.1.8), fenbuconazole (B.1.9), fluquinconazole (B.1.10), flusilazole (B.1.1 1), flutriafol (B.1.12), hexaconazole (B.1.13), imibenconazole (B.1.14), ipconazole (B.1.15), metconazole (B.1.17), myclobutanil (B.1.18), oxpoconazole (B.1.19), paclobutrazole (B.1.20), penconazole (B.1.21), propiconazole (B.
  • benalaxyl (C.1.1), benalaxyl-M (C.1.2), kiralaxyl (C.1.3), metalaxyl (C.1.4), metalaxyl-M (C.1.5), ofurace (C.1.6), oxadixyl (C.1.7);
  • nucleic acid synthesis inhibitors hymexazole (C.2.1), octhilinone (C.2.2), oxolinic acid (C.2.3), bupirimate (C.2.4), 5-fluorocytosine (C.2.5), 5-fluoro-2-(p-tolylmethoxy)pyrimidin- 4-amine (C.2.6), 5-fluoro-2-(4-fluorophenylmethoxy)pyrimidin-4-amine (C.2.7), 5-fluoro- 2-(4-chlorophenylmethoxy)pyrimidin-4 amine (C.2.8);
  • tubulin inhibitors benomyl (D.1.1), carbendazim (D.1.2), fuberidazole (D1.3), thiabendazole (D.1.4), thiophanate-methyl (D.1.5), 3-chloro-4-(2,6-difluorophenyl)-6-methyl-5-phenyl-pyrida- zine (D.1.6), 3-chloro-6-methyl-5-phenyl-4-(2,4,6-trifluorophenyl)pyridazine (D.1.7), N-e thyl-2- [(3-ethynyl-8-methyl-6-quinolyl)oxy]butanamide (D.1.8), /V-ethyl-2-[(3-ethynyl-8-methyl-
  • diethofencarb (D.2.1), ethaboxam (D.2.2), pencycuron (D.2.3), fluopicolide (D.2.4), zoxamide (D.2.5), metrafenone (D.2.6), pyriofenone (D.2.7);
  • cyprodinil E.1.1
  • mepanipyrim E.1.2
  • pyrimethanil E.1.3
  • blasticidin-S (E.2.1), kasugamycin (E.2.2), kasugamycin hydro- chloride-hydrate (E.2.3), mildiomycin (E.2.4), streptomycin (E.2.5), oxytetracyclin (E.2.6);
  • fluoroimid F.1.1
  • iprodione F.1.2
  • procymidone F.1.3
  • vinclozolin F.1.4
  • fludioxonil F.1.5
  • quinoxyfen F.2.1
  • - Phospholipid biosynthesis inhibitors edifenphos (G.1.1), iprobenfos (G.1.2), pyrazophos
  • dimethomorph G.3.1
  • flumorph G.3.2
  • mandipropamid G.3.3
  • pyrimorph G.3.4
  • benthiavalicarb G.3.5
  • iprovalicarb G.3.6
  • valifenalate G.3.7
  • propamocarb (G.4.1);
  • oxathiapiprolin G.5.1
  • 2- ⁇ 3-[2-(1- ⁇ [3,5-bis(difluoromethyl- 1 / pyrazol-1-yl]acetyl ⁇ piperidin-4-yl)-1 ,3-thiazoM-yl]-4, 5-dihydro- 1 ,2-oxazol-5-yl ⁇ phenyl methanesulfonate G.5.2
  • 2- ⁇ 3-[2-(1 - ⁇ [3,5-bis(difluoromethyl)-1 /fpyrazol-1-yl]acetyl ⁇ piperidin-4- yl) 1 ,3-thiazol-4-yl]-4,5-dihydro-1 ,2-oxazol-5-yl ⁇ -3-chlorophenyl methanesulfonate G.5.3
  • ferbam H.2.1
  • mancozeb H.2.2
  • maneb H.2.3
  • metam H.2.4
  • metiram H.2.5
  • propineb H.2.6
  • thiram H.2.7
  • zineb H.2.8
  • ziram H.2.9
  • organochlorine compounds anilazine (H.3.1), chlorothalonil (H.3.2), captafol (H.3.3), captan (H.3.4), folpet (H.3.5), dichlofluanid (H.3.6), dichlorophen (H.3.7), hexachlorobenzene (H.3.8), pentachlorphenole (H.3.9) and its salts, phthalide (H.3.10), tolylfluanid (H.3.1 1);
  • guanidine H.4.1
  • dodine H.4.2
  • dodine free base H.4.3
  • guazatine H.4.4
  • guazatine-acetate H.4.5
  • iminoctadine H.4.6
  • iminoctadine-triacetate H.4.7
  • iminoctadine-tris(albesilate) H.4.8
  • dithianon H.4.9
  • 2,6-dimethyl-1 /7,5/f[1 ,4]dithiino[2,3- c:5,6-c']dipyrrole-1 ,3,5,7(2/7,6//)-tetraone H.4.10
  • glucan synthesis validamycin (1.1.1), polyoxin B (1.1.2); - melanin synthesis inhibitors: pyroquilon (1.2.1), tricyclazole (I.2.2), carpropamid (I.2.3), dicyclomet (I.2.4), fenoxanil (1.2.5);
  • Microbial pesticides with fungicidal, bactericidal, viricidal and/or plant defense activator activity Ampe!omyces quisqua/is, Aspergillus flavus, Aureobasidium pullulans, Bacillus a!titudinis, B. amyloliquefaciens, B. megaterium, B. mojavensis, B. mycoides, B. pumHus, B. simplex, B.
  • B. subtiHs B. subtiHs var. amyloliquefaciens
  • Candida oieophiia C. saitoana
  • Ciavibacter michiganensis (bacteriophages), Coniothyrium minitans, Cryphonectria parasitica, Cryptococcus a/bidus, Diiophosphora aiopecuri, Fusarium oxysporum, Cionostachys rosea f. catenuiate (also named Giiociadium catenuiatum), Giiociadium roseum, Lysobacter antibioticus, L.
  • Biochemical pesticides with fungicidal, bactericidal, viricidal and/or plant defense activator activity harpin protein, Reynoutria sachaiinensis extract;
  • Microbial pesticides with insecticidal, acaricidal, molluscidal and/or nematicidal activity Agrobacterium radiobacter, Bacillus cere us, B. firm us, B. thuringiensis, B. thuringiensis ssp.
  • HzNPV nucleopolyhedrovirus
  • HzSNPV Heiicoverpa zea single capsid nucleopolyhedrovirus
  • Heterorhabditis bacteriophora i sari a fumosorosea, Lecaniciiiium iongisporum, L. muscarium, Metarhizium anisopiiae, M. anisopiiae var. anisopiiae, M. anisopiiae var. acrid um, Nomuraea riieyi, Paeciiomyces fumosoroseus, P.
  • Microbial pesticides with plant stress reducing, plant growth regulator, plant growth promoting and/or yield enhancing activity Azospiriiium amazonense, A. brasi/ense, A. iipoferum, A. irakense, A. haiopraeferens, Bradyrhizobium spp., B. eikanii, B. japonicum, B. iiaoningense, B. iupini, Delftia acidovorans, Glomus intraradices, Mesorhizobium s p p . , Rhizobium ieguminosarum bv. phaseoii, R. i. bv. trifoiii, R. i. bv. viciae, R. tropici, Sinorhizobium meiiioti,
  • M.1 Acetylcholine esterase (AChE) inhibitors M.1 A carbamates, e.g. aldicarb, alanycarb, bendio- carb, benfuracarb, butocarboxim, butoxycarboxim, carbaryl, carbofuran, carbosulfan, ethiofen-carb, fenobucarb, formetanate, furathiocarb, isoprocarb, methiocarb, methomyl, metolcarb, oxamyl, pirimicarb, propoxur, thiodicarb, thiofanox, trimethacarb, XMC, xylylcarb and triazamate; or M.1 B organophosphates, e.g.
  • GABA-gated chloride channel antagonists M.2A cyclodiene organochlorine compounds, e.g. endosulfan or chlordane; or M.2B fiproles (phenylpyrazoles), e.g. ethiprole, fipronil, flufiprole, pyrafluprole, and pyriprole;
  • M.3 Sodium channel modulators from the class of M.3A pyrethroids e.g. acrinathrin, allethrin, d-cis- trans allethrin, d-trans allethrin, bifenthrin, bioallethrin, bioallethrin S-cylclopentenyl, bio-resmethrin, cycloprothrin, cyfluthrin, beta-cyfluthrin, cyhalothrin, lambda-cyhalothrin, gamma-cyhalothrin, cypermethrin, alpha-cypermethrin, beta-cypermethrin, theta-cypermethrin, zeta-cypermethrin, cyphenothrin, deltamethrin, empenthrin, esfenvalerate, etofenprox, f
  • M.4 Nicotinic acetylcholine receptor agonists M .4A neonicotinoids, e.g. acetamiprid, clothianidin, cycloxaprid, dinotefuran, imidacloprid, nitenpyram, thiacloprid and thiamethoxam; or the compounds M.4A.1 4,5-Dihydro-N-nitro-1-(2-oxiranylmethyl)-1 H-imidazol-2-amine , M .4A.2: (2E-)-1-[(6-Chloropyridin-3-yl)methyl]-N'-nitro-2-pentylidenehydrazinecarboximidamide; or M4.A.3: 1-[(6-Chloropyridin-3-yl)methyl]-7-methyl-8-nitro-5-propoxy-1 ,2,3,5,6,7-hexahydroimidazo[1 ,2- a]pyridine ;
  • Nicotinic acetylcholine receptor allosteric activators e.g. spinosad or spinetoram;
  • M.6 Chloride channel activators from the class of avermectins and milbemycins e.g. abamectin, emamectin benzoate, ivermectin, lepimectin, or milbemectin;
  • M.7 Juvenile hormone mimics such as M.7A juvenile hormone analogues hydroprene, kinoprene, and methoprene; or M.7B fenoxycarb, or M.7C pyriproxyfen; M.8 miscellaneous non-specific (multi-site) inhibitors, e.g. M.8A alkyl halides as methyl bromide and other alkyl halides, M .8B chloropicrin, M.8C sulfuryl fluoride, M.8D borax, or M.8E tartar emetic;
  • M.8A alkyl halides as methyl bromide and other alkyl halides
  • M .8B chloropicrin M.8C sulfuryl fluoride
  • M.8D borax or M.8E tartar emetic
  • M.9 Chordotonal organ TRPV channel modulators e.g. M.9B pymetrozine; pyrifluquinazon;
  • M.10 Mite growth inhibitors e.g. M .10A clofentezine, hexythiazox, and diflovidazin, or M.10B etoxazole;
  • M.1 1 Microbial disruptors of insect midgut membranes, e.g. bacillus thuringiensis or bacillus sphaericus and the insecticdal proteins they produce such as bacillus thuringiensis subsp. is- raelensis, bacillus sphaericus, bacillus thuringiensis subsp. aizawai, bacillus thuringiensis subsp. kurstaki and bacillus thuringiensis subsp. tenebrionis, or the Bt crop proteins: Cry1 Ab, CrylAc, Cryl Fa, Cry2Ab, mCry3A, Cry3Ab, Cry3Bb, and Cry34/35Ab1 ;
  • M.12 Inhibitors of mitochondrial ATP synthase e.g. M.12A diafenthiuron, or M.12B organotin miti- cides such as azocyclotin, cyhexatin, or fenbutatin oxide, M.12C propargite, or M.12D tetradifon; M.13 Uncouplers of oxidative phosphorylation via disruption of the proton gradient, e.g.
  • chlorfenapyr DNOC, or sulfluramid
  • Nicotinic acetylcholine receptor (nAChR) channel blockers e.g. nereistoxin analogues ben- sultap, cartap hydrochloride, thiocyclam, or thiosultap sodium;
  • M.16 Inhibitors of the chitin biosynthesis type 1 e.g. buprofezin;
  • Ecdyson receptor agonists such as diacylhydrazines, e.g. methoxyfenozide, tebufenozide, halofenozide, fufenozide, or chromafenozide;
  • Octopamin receptor agonists e.g. amitraz
  • M.20 Mitochondrial complex III electron transport inhibitors e.g. M.20A hydramethylnon, M .20B acequinocyl, M.20C fluacrypyrim; or M.20D bifenazate;
  • M.21 Mitochondrial complex I electron transport inhibitors e.g. M.21A M ETI acaricides and insec ticides such as fenazaquin, fenpyroximate, pyrimidifen, pyridaben, tebufenpyrad or tolfenpyrad, or M.21 B rotenone;
  • M.22 Voltage-dependent sodium channel blockers e.g. M.22A indoxacarb, M.22B metaflumizone, or M.22B.1 : 2-[2-(4-Cyanophenyl)-1-[3-(trifluoromethyl)phenyl] -, ethylidene]-N-[4- (difluoromethoxy)phenyl]-hydrazinecarboxamide or M.22B.2: N-(3-Chloro-2-methyhphenyl)-2-[(4- chloropheny ⁇ -tmethy methylsulfony aminolphenyll-'methylenel-hydrazinecarboxamide;
  • M.23 Inhibitors of the of acetyl CoA carboxylase such as Tetronic and Tetramic acid derivatives, e.g. spirodiclofen, spiromesifen, or spirotetramat; M.23.1 spiropidion
  • M.24 Mitochondrial complex IV electron transport inhibitors e.g. M.24A phosphine such as alu minium phosphide, calcium phosphide, phosphine or zinc phosphide, or M.24B cyanide;
  • M.25 Mitochondrial complex II electron transport inhibitors such as beta-ketonitrile derivatives, e.g. cyenopyrafen or cyflumetofen; M.28 Ryanodine receptor-modulators from the class of diamides, e.g.
  • M.29 Chordotonal organ Modulators - undefined target site, e.g. flonicamid;
  • M.UN. insecticidal active compounds of unknown or uncertain mode of action e.g. afido-'pyro-pen, afoxolaner, azadirachtin, amidoflumet, benzoximate, broflanilide, bromopropylate, chinomethionat, cryolite, dicloromezotiaz , dicofol, flufenerim, flometoquin, fluensulfone, fluhexafon, fluopyram, fluralaner , metoxadiazone, piperonyl butoxide, pyflu-bumide, pyridalyl, tioxazafen, M.UN.3: 1 1 -(4- chloro-2,6-dimethylphenyl)-12-hydroxy-1 ,4-dioxa-9-azadispiro[4.2.4.2]-tetradec-11 -en-10-one , M.UN.4: 3-(4’-flu
  • M.UN.8 fluazaindolizine ; M.UN.9. a): 4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4H-isoxazol-3-yl]- 2-methyl-N-(1 -oxothietan-3-yl)benzamide ; M .UN.9.b): fluxametamide ; M.UN.10: 5-[3-[2,6-dichloro- 4-(3,3-dichloroallyloxy)phenoxy]propoxy]-1 H-pyrazole;
  • M.UN.1 1.e) N-[3-[[[2-bromo-4-[1 ,2,2,2-tetrafluoro-1 -(trifluoromethyl)ethyl]-6- (trifluoromethyl)phenyl]amino]carbonyl]-2-fluorophenyl]-4-fluoro-N-methyl-benzamide; M.UN.1 1.f) 4- fluoro-N-p-fluoro-S-t -iodo ⁇ l ⁇ -tetrafluoro-l- ⁇ rifluoromethy -'ethyll-O- (trifluoromethyl)phenyl]amino]carbonyl]phenyl]-N-methyl-benzamide; M.UN.1 1.g) 3-fluoro-N-[2- fluoro-3-[[[2-iodo-4-[1 ⁇ -tetrafluoro-l - ⁇ rifluoromethy -'ethyll-O-
  • M.UN.1 1.m N-[5-[[2-bromo-6-chloro-4-[1 ,2,2,3,3,3-hexafluoro-1 -(trifluoromethyl)- propyl]phenyl]carbamoyl]-2-cyano-phenyl]-4-cyano-2-methyl-benzamide; M .UN.1 1.n) 4-cyano-N-[2- cyano-5-[[2,6-dichloro-4-[1 ,2,2,3,3,3-hexafluoro-1-(trifluoromethyl)- propyl]phenyl]carbamoyl]phenyl]-2-methyl-benzamide; M.UN.1 1.o) 4-cyano-N-[2-cyano-5-[[2,6- dichloro ⁇ -tl ⁇ -tetrafluoro-l- ⁇ rifluoromethy ethyllphenyllcarbamoyll-'phenyll ⁇ -methyl- benzamide; M .
  • M.UN.14a 1-[(6-Chloro-3-pyridinyl)methyl]-1 ,2,3,5,6,7-hexahydro-5-methoxy-7-methyl-8-nitro- imidazo[1 ,2-a]pyridine; or M. UN.14b) 1 -[(6-Chloropyridin-3-yl)methyl]-7-methyl-8-nitro-1 ,2,3,5,6,7- hexahydroimidazo[1 ,2-a]pyridin-5-ol;
  • M. UN.16a 1-isopropyl-N,5-dimethyl-N-pyridazin-4-yl-pyrazole-4-carboxamide; or M. UN.16b) 1- (1 ,2-dimethylpropyl)-N-ethyl-5-methyl-N-pyridazin-4-yl-pyrazole-4-carboxamide; M.
  • M.UN.17e 2-(3-pyridinyl)-N-[(tetrahydro-2-furanyl)methyl]-2H-indazole-5-carboxamide
  • M.UN.17f methyl 2-[[2-(3-pyridinyl)-2H-indazol-5-yl]carbonyl]hydrazinecarboxylate
  • M .UN.17g N-[(2,2- difluorocyclopropyl)methyl]-2-(3-pyridinyl)-2H-indazole-5-carboxamide
  • M.UN.17h N-(2,2- difluoropropyl)-2-(3-pyridinyl)-2H-indazole-5-carboxamide
  • M.UN.17i 2-(3-pyridinyl )-N-(2- pyrimidinylmethyl )-2H-indazole-5-carboxamide
  • M.UN.17j N-[(5-methyl-2-pyrazinyl
  • M.UN.21 N-[4-Chloro-3-[[(phenylmethyl)amino]carbonyl]phenyl]-1 -methyl-3-(1 ,1 ,2,2,2- pentafluoroethyl)-4-(trifluoromethyl)-1 H-pyrazole-5-carboxamide ;
  • M.UN.22a 2-(3-ethylsulfonyl-2- pyridyl)-3-methyl-6-(trifluoromethyl)imidazo[4,5-b]pyridine, or M.UN.22b 2-[3-ethylsulfonyl-5- (trifluoromethyl)-2-pyridyl]-3-methyl-6-(trifluoromethyl)imidazo[4,5-b]pyridine ;
  • M. UN.23a 4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4H-isoxazol-3-yl]-N-[(4R)-2-ethyl-3-oxo- isoxazolidin-4-yl]-2-methyl-benzamide, or M. UN.23b 4-[5-(3,5-dichloro-4-fluoro-phenyl)-5- (trifluoromethyl)-4H-isoxazol-3-yl]-N-[(4R)-2-ethyl-3-oxo-isoxazolidin-4-yl]-2-methyl-benzamide ;
  • Lipid biosynthesis inhibitors alloxydim, alloxydim-sodium, butroxydim, clethodim, clodinafop, clodinafop-propargyl, cycloxydim, cyhalofop, cyhalofop-butyl, diclofop, diclofop-methyl, fenoxaprop, fenoxaprop-ethyl, fenoxaprop-P, fenoxaprop-P-ethyl, fluazifop, fluazifop-butyl, fluazifop-P, fluazifop-P-butyl, haloxyfop, haloxyfop-methyl, haloxyfop-P, haloxyfop-P-methyl, metamifop, pinoxaden, profoxydim, propaquizafop, quizalofop, quizalofop-eth
  • b.2 ALS inhibitors amidosulfuron, azimsulfuron, bensulfuron, bensulfuron-methyl, chlorimuron, chlorimuron-ethyl, chlorsulfuron, cinosulfuron, cyclosulfamuron, ethametsulfuron, ethamet- sulfuron-methyl, ethoxysulfuron, flazasulfuron, flucetosulfuron, flupyrsulfuron, flupyrsulfuron- methyl-sodium, foramsulfuron, halosulfuron, halosulfuron-methyl, imazosulfuron, iodosulfuron, iodosulfuron-methyl-sodium, iofensulfuron, iofensulfuron-sodium, mesosulfuron, metazo- sulfuron, metsulfuron, metsulfuron-methyl, nicosulfuron, ortho
  • thifensulfuron-methyl triasulfuron, tribenuron, tribenuron-methyl, trifloxysulfuron, triflusulfuron, triflusulfuron-methyl, tritosulfuron, imazamethabenz, imazamethabenz-methyl, imazamox, imazapic, imazapyr, imazaquin, imazethapyr; cloransulam, cloransulam-methyl, diclosulam, flumetsulam, florasulam, metosulam, penoxsulam, pyrimisulfan, pyroxsulam; bispyribac, bispyribac-sodium, pyribenzoxim, pyriftalid, pyriminobac, pyriminobac-methyl, pyrithiobac, pyrithiobac-sodium, 4-[[[2-[(4,6-dimethoxy-2-pyrimidinyl)oxy]phenyl]
  • Photosynthesis inhibitors amicarbazone; chlorotriazine; ametryn, atrazine, chloridazone,
  • chlorotoluron chloroxuron, dimefuron, diuron, fluometuron, isoproturon, isouron, linuron, metamitron, methabenzthiazuron, metobenzuron, metoxuron, monolinuron, neburon, siduron, tebuthiuron, thiadiazuron, desmedipham, karbutilat, phenmedipham, phenmedipham-ethyl, bromofenoxim, bromoxynil and its salts and esters, ioxynil and its salts and esters, bromacil, lenacil, terbacil, bentazon, bentazon-sodium, pyridate, pyridafol, pentanochlor, propanil; diquat, diquat-dibromide, paraquat, paraquat-dichloride, paraquat-dimetilsulfate;
  • protoporphyrinogen-IX oxidase inhibitors acifluorfen, acifluorfen-sodium, azafenidin, ben- carbazone, benzfendizone, bifenox, butafenacil, carfentrazone, carfentrazone-ethyl, chlor- methoxyfen, cinidon-ethyl, fluazolate, flufenpyr, flufenpyr-ethyl, flumiclorac, flumiclorac-pentyl, flumioxazin, fluoroglycofen, fluoroglycofen-ethyl, fluthiacet, fluthiacet-methyl, fomesafen, halosafen, lactofen, oxadiargyl, oxadiazon, oxyfluorfen, pentoxazone, profluazol, pyraclonil, pyraflufen, pyraflufen-sodium,
  • b.5 Bleacher herbicides beflubutamid, diflufenican, fluridone, flurochloridone, flurtamone,
  • norflurazon picolinafen, 4-(3-trifluoromethyhphenoxy)-2-(4-trifluoromethylphenyl)pyrimidine (180608-33-7); benzobicyclon, benzofenap, bicyclopyrone, clomazone, fenquintrione, isoxaflutole, mesotrione, pyrasulfotole, pyrazolynate, pyrazoxyfen, sulcotrione, tefuryltrione, tembotrione, tolpyralate, topramezone; aclonifen, amitrole, flumeturon;
  • EPSP synthase inhibitors glyphosate, glyphosate-isopropylammonium, glyposate-potassium, glyphosate-trimesium (sulfosate);
  • Glutamine synthase inhibitors bilanaphos (bialaphos), bilanaphos-sodium, glufosinate,
  • glufosinate-P glufosinate-ammonium
  • Mitosis inhibitors benfluralin, butralin, dinitramine, ethalfluralin, fluchloralin, oryzalin, pen- dimethalin, prodiamine, trifluralin; amiprophos, amiprophos-methyl, butamiphos; chlorthal, chlorthal-dimethyl, dithiopyr, thiazopyr, propyzamide, tebutam; carbetamide, chlorpropham, flamprop, flamprop-isopropyl, flamprop-methyl, flamprop-M-isopropyl, flamprop-M-methyl, propham;
  • VLCFA inhibitors acetochlor, alachlor, butachlor, dimethachlor, dimethenamid, dimethenamid- P, metazachlor, metolachlor, metolachlor-S, pethoxamid, pretilachlor, propachlor, propisochlor, thenylchlor, flufenacet, mefenacet, diphenamid, naproanilide, napropamide, napropamide-M, fentrazamide, anilofos, cafenstrole, fenoxasulfone, ipfencarbazone, piperophos, pyroxasulfone, isoxazoline compounds of the formulae 11.1 , II.2, II.3, II.4, II.5, II.6, II.7, II.8 and II.9
  • b.1 1 Cellulose biosynthesis inhibitors: chlorthiamid, dichlobenil, flupoxam, indaziflam, isoxaben, triaziflam, 1-cyclohexyl-5-pentafluorphenyloxy-14-[1 ,2,4,6]thiatriazin-3-ylamine (175899-01-1); b.12 Decoupler herbicides: dinoseb, dinoterb, DNOC and its salts;
  • b.13 Auxinic herbicides 2,4-D and its salts and esters, clacyfos, 2,4-DB and its salts and esters, aminocyclopyrachlor and its salts and esters, aminopyralid and its salts such as aminopyralid- dimethylammonium, aminopyralid-tris(2-hydroxypropyl)ammonium and its esters, benazolin, benazolin-ethyl, chloramben and its salts and esters, clomeprop, clopyralid and its salts and esters, dicamba and its salts and esters, dichlorprop and its salts and esters, dichlorprop-P and its salts and esters, fluroxypyr, fluroxypyr-butometyl, fluroxypyr-meptyl, halauxifen and its salts and esters (943832-60-8); MCPA and its salts and esters, MCPA-thioethyl, MCPB and its
  • b.14 Auxin transport inhibitors diflufenzopyr, diflufenzopyr-sodium, naptalam, naptalam-sodium; b.15 Other herbicides: bromobutide, chlorflurenol, chlorflurenol-methyl, cinmethylin, cumyluron, cyclopyrimorate (499223-49-3) and its salts and esters, dalapon, dazomet, difenzoquat, di- fenzoquat-metilsulfate, dimethipin, DSMA, dymron, endothal and its salts, etobenzanid, flurenol, flurenol-butyl, flurprimidol, fosamine, fosamine-ammonium, indanofan, maleic hydrazide, mefluidide, metam, methiozolin (403640-27-7), methyl azide, methyl bromide, methyl-dymron,
  • abscisic acid (0.1.1), amidochlor, ancymidol, 6-benzylaminopurine, brassinolide, butralin, chlormequat, chlormequat chloride, choline chloride, cyclanilide, daminozide, dikegulac, dimethipin, 2,6-dimethylpuridine, ethephon, flumetralin, flurprimidol, fluthiacet, forchlorfenuron, gibberellic acid, inabenfide, indole-3-acetic acid , maleic hydrazide, mefluidide, mepiquat, mepiquat chloride, naphthaleneacetic acid, / ⁇ A6-benzyladenine, paclobutrazol, prohexadione, prohexadione-calcium, prohydrojasmon, thidiazuron, triapenthenol, tributyl phosphorotrithioate, 2,3,
  • component II The active substances referred to as component II, their preparation and their activity e. g.
  • WO 13/024009 WO 13/24010, WO 13/047441 , WO 13/162072, WO 13/092224, WO 1 1/135833, ON 1907024, ON 1456054, ON 103387541 , ON 1309897, WO 12/84812, ON 1907024,
  • Some compounds are identified by their CAS Registry Number which is separated by hyphens into three parts, the first consisting from two up to seven digits, the second consisting of two digits, and the third consisting of a single digit.
  • the present invention furthermore relates to agrochemical compositions comprising a mixture of at least one compound of formula (I) (component I) and at least one further active substance useful for plant protection, e. g. selected from the groups A) to O) (component II) and/or selected from groups M.1 to M.29.
  • agrochemical compositions comprising a mixture of at least one compound of formula (I) (component I) and at least one further active substance useful for plant protection, e. g. selected from the groups A) to O) (component II) and/or selected from groups M.1 to M.29.
  • the compounds of formula (I) and at least one further active substance simultaneously can be applied either jointly (e. g. as tank-mix) or seperately, or in succession, wherein the time interval between the individual applications is selected to ensure that the active substance applied first still occurs at the site of action in a sufficient amount at the time of application of the further active substance(s).
  • the order of application is not essential for working of the present invention.
  • the time between both applications may vary e. g. between 2 hours to 7 days. Also, a broader range is possible ranging from 0.25 hour to 30 days, preferably from 0.5 hour to 14 days, particularly from 1 hour to 7 days or from 1.5 hours to 5 days, even more preferred from 2 hours to 1 day.
  • the pesticide II is applied as last treatment.
  • the present invention provides the agricultural mixtures wherein the compound of formula (I) is selected from compounds of formula
  • the present invention provides agricultural mixtures comprising,
  • M.1 Acetylcholine esterase (AChE) inhibitors M.1 A carbamates, e.g. aldicarb, alanycarb, bendio- carb, benfuracarb, butocarboxim, butoxycarboxim, carbaryl, carbofuran, carbosulfan, ethiofen-carb, fenobucarb, formetanate, furathiocarb, isoprocarb, methiocarb, methomyl, metolcarb, oxamyl, pirimicarb, propoxur, thiodicarb, thiofanox, trimethacarb, XMC, xylylcarb and triazamate; or M.1 B organophosphates, e.g.
  • GABA-gated chloride channel antagonists M.2A cyclodiene organochlorine compounds, e.g. endosulfan or chlordane; or M.2B fiproles (phenylpyrazoles), e.g. ethiprole, fipronil, flufiprole, pyrafluprole, and pyriprole;
  • M.3 Sodium channel modulators from the class of M.3A pyrethroids e.g. acrinathrin, allethrin, d-cis- trans allethrin, d-trans allethrin, bifenthrin, bioallethrin, bioallethrin S-cylclopentenyl, bio-resmethrin, cycloprothrin, cyfluthrin, beta-cyfluthrin, cyhalothrin, lambda-cyhalothrin, gamma-cyhalothrin, cypermethrin, alpha-cypermethrin, beta-cypermethrin, theta-cypermethrin, zeta-cypermethrin, cyphenothrin, deltamethrin, empenthrin, esfenvalerate, etofenprox, f
  • M.4 Nicotinic acetylcholine receptor agonists M.4A neonicotinoids, e.g. acetamiprid, clothianidin, cycloxaprid, dinotefuran, imidacloprid, nitenpyram, thiacloprid and thiamethoxam; or the compounds M.4A.1 4,5-Dihydro-N-nitro-1-(2-oxiranylmethyl)-1 H-imidazol-2-amine , M .4A.2: (2E-)-1-[(6-Chloropyridin-3-yl)methyl]-N , -nitro-2-pentylidenehydrazinecarboximidamide; or M4.A.3: 1-[(6-Chloropyridin-3-yl)methyl]-7-methyl-8-nitro-5-propoxy-1 ,2,3,5,6,7-hexahydroimidazo[1 ,2- a]pyridine
  • M.7 Juvenile hormone mimics such as M.7A juvenile hormone analogues hydroprene, kinoprene, and methoprene; or M.7B fenoxycarb, or M.7C pyriproxyfen;
  • M.8 miscellaneous non-specific (multi-site) inhibitors e.g. M.8A alkyl halides as methyl bromide and other alkyl halides, M .8B chloropicrin, M.8C sulfuryl fluoride, M.8D borax, or M.8E tartar emetic;
  • M.9 Chordotonal organ TRPV channel modulators e.g. M.9B pymetrozine; pyrifluquinazon;
  • M.10 Mite growth inhibitors e.g. M.10A clofentezine, hexythiazox, and diflovidazin, or M.10B etoxazole;
  • M.1 1 Microbial disruptors of insect midgut membranes, e.g. bacillus thuringiensis or bacillus sphaericus and the insecticdal proteins they produce such as bacillus thuringiensis subsp. is- raelensis, bacillus sphaericus, bacillus thuringiensis subsp. aizawai, bacillus thuringiensis subsp. kurstaki and bacillus thuringiensis subsp. tenebrionis, or the Bt crop proteins: Cry1 Ab, CrylAc, Cryl Fa, Cry2Ab, mCry3A, Cry3Ab, Cry3Bb, and Cry34/35Ab1 ;
  • M.12 Inhibitors of mitochondrial ATP synthase e.g. M.12A diafenthiuron, or M.12B organotin miti- cides such as azocyclotin, cyhexatin, or fenbutatin oxide, M.12C propargite, or M.12D tetradifon; M.13 Uncouplers of oxidative phosphorylation via disruption of the proton gradient, e.g.
  • chlorfenapyr DNOC, or sulfluramid
  • Nicotinic acetylcholine receptor (nAChR) channel blockers e.g. nereistoxin analogues ben- sultap, cartap hydrochloride, thiocyclam, or thiosultap sodium;
  • M.16 Inhibitors of the chitin biosynthesis type 1 e.g. buprofezin;
  • Ecdyson receptor agonists such as diacylhydrazines, e.g. methoxyfenozide, tebufenozide, halofenozide, fufenozide, or chromafenozide;
  • Octopamin receptor agonists e.g. amitraz
  • M.20 Mitochondrial complex III electron transport inhibitors e.g. M.20A hydramethylnon, M.20B acequinocyl, M.20C fluacrypyrim; or M.20D bifenazate;
  • M.21 Mitochondrial complex I electron transport inhibitors e.g. M.21A M ETI acaricides and insec ticides such as fenazaquin, fenpyroximate, pyrimidifen, pyridaben, tebufenpyrad or tolfenpyrad, or M.21 B rotenone;
  • M.22 Voltage-dependent sodium channel blockers e.g. M.22A indoxacarb, M.22B metaflumizone, or M.22B.1 : 2-[2-(4-Cyanophenyl)-1-[3-(trifluoromethyl)phenyl] -, ethylidene]-N-[4- (difluoromethoxy)phenyl]-hydrazinecarboxamide or M.22B.2: N-(3-Chloro-2-methyhphenyl)-2-[(4- chloropheny ⁇ -tmethy methylsulfonyOaminolphenyl ⁇ methylenel-hydrazinecarboxamide;
  • M.23 Inhibitors of the of acetyl CoA carboxylase such as Tetronic and Tetramic acid derivatives, e.g. spirodiclofen, spiromesifen, or spirotetramat; M.23.1 spiropidion
  • M.24 Mitochondrial complex IV electron transport inhibitors e.g. M.24A phosphine such as alu minium phosphide, calcium phosphide, phosphine or zinc phosphide, or M.24B cyanide;
  • Mitochondrial complex II electron transport inhibitors such as beta-ketonitrile derivatives, e.g. cyenopyrafen or cyflumetofen;
  • M.28 Ryanodine receptor-modulators from the class of diamides e.g. flubendiamide, chlor- antraniliprole, cyantraniliprole, tetraniliprole, M.28.1 : (R)-3-Chlor-N1- ⁇ 2-methyl-4-[1 ,2,2,2 - tetrafluoro-1 -(trifluoromethyl)ethyl]phenyl ⁇ -N2-(1-methyl-2-methylsulfonylethyl)phthalamid, M.28.2: (S)-3-Chloro-N 1 - ⁇ 2-methyl-4-[1 ,2,2,2-tetrafluoro-1 -(trifluoromethyl)ethyl]phenyl ⁇ -N2-(1 -methyl-2- methylsulfonylethyl)phthalamid, M.28.3: cyclaniliprole, or M.28.4: methyl-2-[3,5-dibromo-2-(
  • M.29 Chordotonal organ Modulators - undefined target site, e.g. flonicamid;
  • M.UN. insecticidal active compounds of unknown or uncertain mode of action e.g. afido-'pyro-pen, afoxolaner, azadirachtin, amidoflumet, benzoximate, broflanilide, bromopropylate, chinomethionat, cryolite, dicloromezotiaz , dicofol, flufenerim, flometoquin, fluensulfone, fluhexafon, fluopyram, fluralaner , metoxadiazone, piperonyl butoxide, pyflu-bumide, pyridalyl, tioxazafen, M.UN.3: 1 1 -(4- chloro-2,6-dimethylphenyl)-12-hydroxy-1 ,4-dioxa-9-azadispiro[4.2.4.2]-tetradec-11 -en-10-one , M.UN.4: 3-(4’-flu
  • M.UN.6 flupyrimin
  • M.UN.8 fluazaindolizine
  • M.UN.9.b fluxametamide
  • M.UN.10 5-[3-[2,6-dichloro- 4-(3,3-dichloroallyloxy)phenoxy]propoxy]-1 H-pyrazole;
  • M.UN.1 1.e) N-[3-[[[2-bromo-4-[1 ,2,2,2-tetrafluoro-1 -(trifluoromethyl)ethyl]-6- (trifluoromethyl)phenyl]amino]carbonyl]-2-fluorophenyl]-4-fluoro-N-methyl-benzamide; M.UN.1 1.f) 4- fluoro-N-p-fluoro-S-t -iodo ⁇ l ⁇ -tetrafluoro-l- ⁇ rifluoromethy -'ethyll-O- (trifluoromethyl)phenyl]amino]carbonyl]phenyl]-N-methyl-benzamide; M.UN.1 1.g) 3-fluoro-N-[2- fluoro-3-[[[2-iodo-4-[1 ⁇ -tetrafluoro-l - ⁇ rifluoromethyO-Othyll-O-O-O-
  • M.UN.1 4-cyano-N-[2-cyano-5-[[2,6-dibromo-4-[1 ,2,2,3,3,3-hexafluoro- 1-(trifluoromethyl)-propyl]phenyl]carbamoyl]phenyl]-2-methyl-benzamide; M .UN.1 1.j) 4-cyano-3-[(4- cyano-2-methyl-benzoyl)amino]-N-[2,6-dichloro-4-[1 ,2,2,3,3,3-hexafluoro-1- (trifluoromethy -'propyllphenyll ⁇ -fluoro-benzamide; M.UN.11.k) N-[5-[[2-chloro-6-cyano ⁇ l- [1 ,2,2,3,3,3-hexafluoro-1-(trifluoromethyl)propyl]phenyl]carbamoyl]-2-cyano-phenyl]
  • M.UN.1 1.m N-[5-[[2-bromo-6-chloro-4-[1 ,2,2,3,3,3-hexafluoro-1 -(trifluoromethyl)- propyl]phenyl]carbamoyl]-2-cyano-phenyl]-4-cyano-2-methyl-benzamide; M .UN.1 1.n) 4-cyano-N-[2- cyano-5-[[2,6-dichloro-4-[1 ,2,2,3,3,3-hexafluoro-1-(trifluoromethyl)- propyl]phenyl]carbamoyl]phenyl]-2-methyl-benzamide; M.UN.1 1.o) 4-cyano-N-[2-cyano-5-[[2,6- dichloro ⁇ -tl ⁇ -tetrafluoro-l- ⁇ rifluoromethy ethyllphenyllcarbamoyll-'phenyll ⁇ -methyl- benzamide; M .
  • UN.14a 1-[(6-Chloro-3-pyridinyl)methyl]-1 ,2,3,5,6,7-hexahydro-5-methoxy-7-methyl-8-nitro- imidazo[1 ,2-a]pyridine; or M. UN.14b) 1 -[(6-Chloropyridin-3-yl)methyl]-7-methyl-8-nitro-1 ,2,3,5,6,7- hexahydroimidazo[1 ,2-a]pyridin-5-ol;
  • M. UN.16a 1-isopropyl-N,5-dimethyl-N-pyridazin-4-yl-pyrazole-4-carboxamide; or M. UN.16b) 1- (1 ,2-dimethylpropyl)-N-ethyl-5-methyl-N-pyridazin-4-yl-pyrazole-4-carboxamide; M.
  • M.UN.17e 2-(3-pyridinyl)-N-[(tetrahydro-2-furanyl)methyl]-2H-indazole-5-carboxamide; M.UN.17 ⁇ ) methyl 2-[[2-(3-pyridinyl)-2H-indazol-5-yl]carbonyl]hydrazinecarboxylate; M .UN.17g) N-[(2,2- difluorocyclopropyl)methyl]-2-(3-pyridinyl)-2H-indazole-5-carboxamide; M.UN.17h) N-(2,2- difluoropropyl)-2-(3-pyridinyl)-2H-indazole-5-carboxamide; M.UN.17i) 2-(3-pyridinyl )-N-(2- pyrimidinylmethyl )-2H-indazole-5-carboxamide; M.UN.17j) N-[(5-methyl-2-pyrazinyl
  • M.UN.21 N-[4-Chloro-3-[[(phenylmethyl)amino]carbonyl]phenyl]-1 -methyl-3-(1 ,1 ,2,2,2- pentafluoroethyl)-4-(trifluoromethyl)-1 H-pyrazole-5-carboxamide ;
  • M.UN.22a 2-(3-ethylsulfonyl-2- pyridyl)-3-methyl-6-(trifluoromethyl)imidazo[4,5-b]pyridine, or M.UN.22b 2-[3-ethylsulfonyl-5- (trifluoromethyl)-2-pyridyl]-3-methyl-6-(trifluoromethyl)imidazo[4,5-b]pyridine ;
  • M. UN.23a 4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4H-isoxazol-3-yl]-N-[(4R)-2-ethyl-3-oxo- isoxazolidin-4-yl]-2-methyl-benzamide, or M. UN.23b 4-[5-(3,5-dichloro-4-fluoro-phenyl)-5- (trifluoromethyl)-4H-isoxazol-3-yl]-N-[(4R)-2-ethyl-3-oxo-isoxazolidin-4-yl]-2-methyl-benzamide ;
  • the present invention provides agricultural mixtures, comprising the compound of formula (la), and at least one pesticidal compound selected from group M consisting of:
  • M.3 Sodium channel modulators from the class of M.3A pyrethroids e.g. acrinathrin, allethrin, d-cis- trans allethrin, d-trans allethrin, bifenthrin, bioallethrin, bioallethrin S-cylclopentenyl, bio-resmethrin, cycloprothrin, cyfluthrin, beta-cyfluthrin, cyhalothrin, lambda-cyhalothrin, gamma-cyhalothrin, cypermethrin, alpha-cypermethrin, beta-cypermethrin, theta-cypermethrin, zeta-cypermethrin, cyphenothrin, deltamethrin, empenthrin, esfenvalerate, etofenprox, f
  • M.4 Nicotinic acetylcholine receptor agonists M.4A neonicotinoids, e.g. acetamiprid, clothianidin, cycloxaprid, dinotefuran, imidacloprid, nitenpyram, thiacloprid and thiamethoxam; or the compounds M.4A.1 4,5-Dihydro-N-nitro-1-(2-oxiranylmethyl)-1 H-imidazol-2-amine , M .4A.2: (2E-)-1-[(6-Chloropyridin-3-yl)methyl]-N'-nitro-2-pentylidenehydrazinecarboximidamide; or M4.A.3: 1-[(6-Chloropyridin-3-yl)methyl]-7-methyl-8-nitro-5-propoxy-1 ,2,3,5,6,7-hexahydroinnidazo[1 ,2- a]pyridine

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Abstract

La présente invention concerne l'utilisation de composés de formule (I) en tant qu'inhibiteur de glutathion S-transférase. L'invention concerne en outre un procédé de lutte contre des parasites agricoles et/ou des parasites non agricoles qui sont résistants à un ou plusieurs insecticides et un procédé de lutte contre la végétation indésirable qui est résistante à un ou plusieurs herbicides par application d'au moins un inhibiteur de glutathion S-transférase (GST) de formule (I).
PCT/IB2019/051801 2018-03-14 2019-03-06 Nouvelles utilisations de molécules de catéchol en tant qu'inhibiteurs de voies métaboliques de glutathion s-transférase WO2019175712A1 (fr)

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2024059011A1 (fr) * 2022-09-13 2024-03-21 The United States Of America, As Represented By The Secretary Of Agriculture Compositions et méthodes pour lutter contre les organismes nuisibles

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CHEMICAL ABSTRACTS, Columbus, Ohio, US; abstract no. 420138-01-8
CHEMICAL ABSTRACTS, Columbus, Ohio, US; abstract no. 420138-40-5
CHEMICAL ABSTRACTS, Columbus, Ohio, US; abstract no. 420138-41-6
CHEMICAL ABSTRACTS, Columbus, Ohio, US; abstract no. 451484-50-7
CHEMICAL ABSTRACTS, Columbus, Ohio, US; abstract no. 452098-92-9
CHEMICAL ABSTRACTS, Columbus, Ohio, US; abstract no. 452099-05-7
CHEMICAL ABSTRACTS, Columbus, Ohio, US; abstract no. 452100-03-7
CHEMICAL ABSTRACTS, Columbus, Ohio, US; abstract no. 499223-49-3
CHEMICAL ABSTRACTS, Columbus, Ohio, US; abstract no. 52836-31-4
CHEMICAL ABSTRACTS, Columbus, Ohio, US; abstract no. 54091-06-4
CHEMICAL ABSTRACTS, Columbus, Ohio, US; abstract no. 71526-07-3
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CHEMICAL ABSTRACTS, Columbus, Ohio, US; abstract no. 81778-66-7
CHEMICAL ABSTRACTS, Columbus, Ohio, US; abstract no. 915396-43-9
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WO2024059011A1 (fr) * 2022-09-13 2024-03-21 The United States Of America, As Represented By The Secretary Of Agriculture Compositions et méthodes pour lutter contre les organismes nuisibles

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