WO2026008750A1 - Novel carboxamide compounds - Google Patents

Abstract

Compounds of formula (I) wherein the substituents are as defined in the claims, and processes for their preparation, to compositions comprising the compounds, and to their use for controlling animal pests, including arthropods and in particular insects.

Description

NOVEL CARBOXAMIDE COMPOUNDS

The present invention relates to pesticidally active, in particular insecticidally active carboxamide compounds, preferably substituted carboxamide compounds thereof, to processes for their preparation, to compositions comprising the compounds, and to their use for controlling animal pests, including arthropods and in particular insects.

WO 2021/153720 describes certain alkoxy benzoic acid amide derivatives.

There have now been found certain novel pesticidally active carboxamide compounds.

The present invention accordingly relates, in a first aspect, to a compound of the formula (I) wherein

R¹ is selected from hydrogen, Ci-C4-alkyl, Ci-C4-haloalkyl, Cs-Ce-cycloalkyl, Cs-Ce-halocycloalkyl, cyano-Ci- C4-alkyl, C3-C6-cycloalkyl-Ci-C4-alkyl, cyano-Cs-Ce-cycloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, C2-C4- alkynyloxy, Ci-C4-alkoxy-Ci-C4-alkyl, Ci-C4-alkoxy-Ci-C4-alkoxy, C3-C6-cycloalkyl-Ci-C4-alkoxy, C3-C6- cycloalkyloxy, N-(Ci-C4-alkyl)amino, N-(C3-C6-cycloalkyl)amino, N,N-di(Ci-C4-alkyl)amino, Ci-C4-alkoxyamino- Ci-C4-alkyl, Ci-C4-alkoxyimino, Ci-C4-alkylsulfonyl-Ci-C4-alkyl, Ci-C4-alkylsulfanyl-Ci-C4-alkyl, C1-C4- alkoxycarbonyl-Ci-C4-alkyl, Ci-C4-alkylcarbonyloxy-Ci-C4-alkyl, Ci-C4-alkylcarbonylamino-Ci-C4-alkyl, C1-C4- alkoxycarbonylamino-Ci-C4-alkyl, phenoxy-Ci-C4-alkyl, phenoxy, Cs-Cs-bicycloalkyl, 3-, 4-, 5- or 6-membered heterocycloalkyl, phenyl, phenyl-Ci-C4-alkyl, 5- or 6-membered heteroaryl, or 5- or 6-membered heteroaryl-Ci- Cs-alkyl; wherein any of said 3-, 4-, 5- or 6-membered heterocycloalkyl contains 1 or 2 heteroatoms or groups individually selected from N, O, S, S=O, or SO2, with the proviso that no more than one is O, S, S=O or SO2; wherein any of said 5- or 6-membered heteroaryl and heteroaryl-Ci-Cs-alkyl contains 1 , 2, 3 or 4 heteroatoms individually selected from N, S, or O, with the proviso that no more than one is O or S; wherein any of said C3- Ce-cycloalkyl, and 3-, 4-, 5- or 6-membered heterocycloalkyl are unsubstituted or substituted by 1 , 2 or 3 substituents independently selected from halogen, cyano, Ci-Cs-alkyl, Ci-Cs-haloalkyl, or Cs-Ce-cycloalkyl; and wherein any of said phenyl, said 5- or 6-membered heteroaryl and heteroaryl-Ci-Cs-alkyl are unsubstituted or substituted by 1 , 2 or 3 substituents independently selected from halogen, cyano, Ci-C4-alkyl, Ci-C4-haloalkyl, or Ci-C4-alkoxy;

R² is selected from hydrogen, Ci-C4-alkyl, Ci-C4-alkoxy, Ci-C4-alkoxy-Ci-C4-alkyl, cyano-Ci-C4-alkyl, C1-C4- alkylcarbonyl or Ci-C4-alkoxycarbonyl;

R³ is selected from hydrogen, or Ci-Cs-alkyl;

R⁴ is selected from hydrogen, halogen, or Ci-Cs-alkyl;

R⁵ and R⁶ are independently selected from hydrogen, or Ci-Cs-alkyl; or R⁵ and R⁶ together with the carbon to which they are attached represent a Cs-Cs-cycloalkyl group; R⁷ is selected from Ci-C4-alkyl, Ci-C4-haloalkyl, Cs-Ce-cycloalkyl, phenyl, or 5- or 6-membered heteroaryl; wherein any of said Cs-Ce-cycloalkyl is unsubstituted or substituted by 1 , 2 or 3 substituents independently selected from halogen, cyano, Ci-Cs-alkyl, or Ci-Cs-haloalkyl; wherein any of said 5- or 6-membered heteroaryl contains 1 or 2 heteroatoms individually selected from N, S or O, with the proviso that no more than one is O or S; and wherein any of said phenyl, and said 5- or 6-membered heteroaryl are unsubstituted or substituted by 1 , 2 or 3 substituents independently selected from halogen, cyano, Ci-C4-alkyl, Ci-C4-haloalkyl, or C1-C4- alkoxy; and

R⁸ is selected from hydrogen, Ci-C4-alkyl, Ci-C4-alkoxy, Ci-C4-alkoxy-Ci-C4-alkyl, cyano-Ci-C4-alkyl, C1-C4- alkylcarbonyl, Ci-C4-alkoxycarbonyl, Ci-C4-haloalkoxycarbonyl, Ci-C4-alkylcarbonyloxy-Ci-C4-alkyl, N,N-di(Ci- C4-alkyl)aminocarbonyl, or Cs-Ce-cycloalkyloxycarbonyl; or a salt or an N-oxide thereof.

Surprisingly, it has been found that the novel compounds of formula (I) have, for practical purposes, advantageous levels of biological activity for protecting plants against insects or superior properties for use as agrochemical active ingredients, for example, greater biological activity, an advantageous spectrum of activity, an increased safety profile against non-target organisms above and below ground (such as fish, birds and bees), improved physico-chemical properties, or increased biodegradability.

According to a second aspect of the invention, there is provided a composition comprising a compound of formula (I) as defined in the first aspect. Such a composition may further comprise at least one additional active ingredient and/or an agrochemically-acceptable diluent or carrier.

According to a third aspect of the invention, there is provided a method of combating and controlling insects, acarines, nematodes or molluscs which comprises applying to a pest, to a locus of a pest, or to a plant susceptible to attack by a pest an insecticidally, acaricidally, nematicidally, or molluscicidally effective amount of a compound as defined in the first aspect or a composition as defined in the second aspect.

According to a fourth aspect of the invention, there is provided a method for the protection of plant propagation material from the attack by insects, acarines, nematodes, or molluscs, which comprises treating the propagation material or the site, where the propagation material is planted, with an effective amount of a compound of formula (I) as defined in the first aspect or a composition as defined in the second aspect.

According to a fifth aspect of the invention, the present invention makes available a plant propagation material, such as a seed, comprising, or treated with or adhered thereto, a compound of formula (I) as defined in the first aspect, or a composition as defined in the second aspect.

Compounds of formula (I) which have at least one basic centre can form, for example, acid addition salts, for example with strong inorganic acids such as mineral acids, e.g., perchloric acid, sulfuric acid, nitric acid, nitrous acid, a phosphorus acid or a hydrohalic acid, with strong organic carboxylic acids, such as C1- C4alkanecarboxylic acids which are unsubstituted or substituted, for example by halogen, e.g., acetic acid, such as saturated or unsaturated dicarboxylic acids, e.g., oxalic acid, malonic acid, succinic acid, maleic acid, fumaric acid or phthalic acid, such as hydroxycarboxylic acids, e.g., ascorbic acid, lactic acid, malic acid, tartaric acid or citric acid, or such as benzoic acid, or with organic sulfonic acids, such as Ci-C4alkane- or arylsulfonic acids which are unsubstituted or substituted, for example by halogen, e.g., methane- or p-toluenesulfonic acid. Compounds of formula (I) which have at least one acidic group can form, for example, salts with bases, e.g., mineral salts such as alkali metal or alkaline earth metal salts, e.g., sodium, potassium or magnesium salts, or salts with ammonia or an organic amine, such as morpholine, piperidine, pyrrolidine, a mono-, di- or tri-lower- alkylamine, e.g., ethyl-, diethyl-, triethyl- or dimethylpropylamine, or a mono-, di- or trihydroxy-lower-alkylamine, e.g., mono-, di- or triethanolamine.

In each case, the compounds of formula (I) according to the invention are in free form, in oxidized form as a N- oxide or in salt form, e.g., an agronomically usable salt form. N-oxides are oxidized forms of tertiary amines or oxidized forms of nitrogen containing heteroaromatic compounds. They are described for instance in the book “Heterocyclic N-oxides” by A. Albini and S. Pietra, CRC Press, Boca Raton 1991 . The compounds of formula (I) according to the invention also include hydrates which may be formed during the salt formation.

As used herein, the term "halogen" or “halo” refers to fluorine (fluoro), chlorine (chloro), bromine (bromo) or iodine (iodo), preferably fluorine, chlorine, or bromine. This also applies, correspondingly, to halogen in combination with other meanings, such as haloalky I, and halocycloalkyl.

As used herein, cyano means a -CN group.

As used herein, phenoxy means a -Ophenyl (OPh) group.

As used herein, the term "Ci-C_n-alkyl” refers to a saturated straight-chain or branched hydrocarbon radical attached via any of the carbon atoms having 1 to n carbon atoms, for example, any one of the radicals methyl, ethyl, n-propyl, 1 -methylbutyl, 2-methylbutyl, 3-methylbutyl, 2, 2-dimethylpropyl, 1 -ethylpropyl, n-hexyl, n- pentyl, 1 ,1-dimethylpropyl, 1 , 2-dimethylpropyl, 1 -methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl,

1 .1 -dimethylbutyl, 1 ,2-dimethylbutyl, 1 ,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1 -ethylbutyl, 2-ethylbutyl, 1 ,1 ,2-trimethylpropyl, 1 ,2,2-trimethylpropyl, 1-ethyl-1 -methylpropyl, or 1-ethyl-2- methylpropyl.

As used herein, the term “C2-C_n-alkynyl” refers to a straight or branched alkynyl chain moiety having from two to n carbon atoms and one triple bond, for example, ethynyl, prop-2-ynyl (propargyl), but-3-ynyl.

As used herein, the term “Cs-Cn-cycloalkyl” refers to 3 to n membered cycloalkyl radical such as cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl.

As used herein, the term "Ci-C_n-alkoxy" refers to a straight-chain or branched saturated alkyl radical having 1 to n carbon atoms (as mentioned above) which is attached via an oxygen atom, e.g., for example, any one of the radicals methoxy, ethoxy, n-propoxy, 1 -methylethoxy, n-butoxy, 1 -methylpropoxy, 2-methylpropoxy, and

1 .1 -dimethylethoxy.

As used herein, the term "Ci-C_n-alkylamino" refers to a straight-chain or branched saturated alkyl radical having

1 to n carbon atoms (as mentioned above) which is attached via a nitrogen atom, e.g., for example, any one of the radicals methylamino, ethylamino, n-propylamino, 1 -methylethylamino, n-butylamino, 1- methylpropylamino, 2-methylpropylamino, and 1 ,1-dimethylethylamino.

As used herein, the term "C2-C_n-alkynyloxy" refers to a radical of the formula -OR_a where R_a is a C2-Cn-alkynyl radical as generally defined above.

As used herein, the term " Cs-Cn-cycloalkyloxy" refers to a radical of the formula -OR_a where R_a is a C3-C_n- cycloalkyl radical as generally defined above.

As used herein, the term " Cs-Cn-cycloalkylamino" refers to a radical of the formula -N(H)R_a where R_a is a C3- Cn-cycloalkyl radical as generally defined above.

As used herein, the term "C2-C_n-alkoxyimino" refers to a radical of the formula -C=N-R_a where R_a is a Ci-C_n- alkoxy radical as generally defined above.

As used herein, the term “Ci-C_n-alkoxy-Ci-C_n-alkyl” refers to an alkyl radical (as mentioned above) substituted with a Ci-Cn-alkoxy group. Examples are methoxymethyl, methoxyethyl, ethoxymethyl, and propoxymethyl.

As used herein, the term “Ci-C_n-alkoxy-Ci-C_n-alkoxy” refers to an alkoxyl radical (as mentioned above) substituted with a Ci-C_n-alkoxy group. Examples are methoxymethoxy ,2-methoxyethoxy, ethoxymethoxy, and 3-methoxypropoxy.

As used herein, the term “C3-C_n-cycloalkyl-Ci-C_n-alkyl” refers to an alkyl radical (as mentioned above) substituted with a Cs-Cn-cycloalkyl group. Examples are cyclopropylmethyl, cyclopropylethyl. Similarly, the term “C3-Cn-halocycloalkyl-Ci-C_n-alkyl” refers to an alkyl radical substituted with cycloalkyl group, wherein the cycloalkyl group is substituted by one or more of the same or different halogen atoms. Examples are 3,3- difluorobutylmethyl, and 1 -chlorocyclopropylmethyl.

As used herein, the term “C3-C_n-cycloalkyl-Ci-C_n-alkoxy” refers to an alkoxy radical (as mentioned above) substituted with a Cs-Cn-cycloalkyl group. Examples are cyclopropylmethoxy, 2-cyclopropylethoxy.

As used herein, the term “Cs-Cn-bicycloalkyl” refers to is an annulated non-aromatic bicyclic ring system comprising two rings fused together (e.g., sharing two carbon atoms), and consisting solely of carbon and hydrogen atoms. Examples are bicyclo[1 .1 .1]pentanyl, bicyclo[3.1 .0]hexan-6-yl, bicyclo[4.1 .0]heptan-7-yl, bicyclo[3.2.0]heptan-6-yl, bicyclo[3.2.0]heptan-3-yl, octahydro-2-pentalenyl, octahydro-1 -pentalenyl.

As used herein, the term “heterocycloalkyl” or “heterocyclyl” refers to a stable 3-, 4-, 5- or 6-membered non- aromatic monocyclic ring radical which contains 1 , 2, or 3 heteroatoms/groups individually selected from N, O, S, S=O or SO2. The heterocyclyl radical may be bonded to the rest of the molecule via a carbon atom or heteroatom. The ring radical will not comprise contiguous oxygen and sulfur atoms. Examples of heterocyclyl include, but are not limited to, epoxide, aziridinyl, pyrrolinyl, pyrrolidyl, tetrahydrofuranyl, tetrahydrothienyl, tetrahydrothiopyranyl, piperidyl, piperazinyl, tetra hydro pyranyl, dioxolanyl, morpholinyl, oxazinanyl, oxetanyl, 1 ,1-dioxothietan-3-yl, or 6-lactamyl. The heterocycloalkyl radical may be substituted on the heteroatom and/or carbon atom. As used herein, the term “cyano-Ci-C_n-alkyl” refers to Ci-C_n-alkyl radical having 1 to n carbon atoms (as mentioned above), where one of the hydrogen atoms in the radical is be replaced by a cyano group: for example, cyano-methyl, 2-cyano-ethyl, 2-cyano-propyl, 3-cyano-propyl, 1-(cyano-methyl)-2-ethyl, 1-(methyl)- 2-cyano-ethyl, 4-cyanobutyl, and the like. Similarly, the term “cyano-Cs-Cn-cycloalkyl” refers to a C3-C_n- cycloalkyl radical substituted with one of the hydrogen atoms by a cyano group; and the term “cyano-Cs-Cn- cycloalkyl-Ci-Cn-alkyl” refers to an Ci-C_n-alkyl radical having a cyano-Cs-Cn-cycloalkyl group.

As used herein, the term “phenoxy-Ci-C_n-alkyl” refers to Ci-C_n-alkyl radical having 1 to n carbon atoms (as mentioned above), where one of the hydrogen atoms in the radical is be replaced by a phenoxy group.

As used herein, the term "Ci-C_n-haloalkyl" refers to a straight-chain or branched saturated alkyl radical attached via any of the carbon atoms having 1 to n carbon atoms (as mentioned above), where some or all of the hydrogen atoms in these radicals may be replaced by fluorine, chlorine, bromine and/or iodine; examples are, but are not limited to, chloromethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 2-fluoroethyl, 2-chloroethyl, 2- bromoethyl, 2-iodoethyl, 2,2-difluoroethy I, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl. Similarly, the term “Ci-C_n-haloalkoxy” as used herein refers to a Ci-Cn-alkoxy radical respectively substituted with one or more halo atoms which may be the same or different. Similarly, the term “Cs-Cn-halocycloalkyl” as used herein refers to a Cs-Cn-cycloalkyl radical respectively substituted with one or more halo atoms which may be the same or different.

As used herein, the term “Ci-C_n-alkylsulfanyl” refers to a radical of the formula -SR_a wherein R_a is a Ci-C_n-alkyl radical as generally defined above.

As used herein, the term “Ci-C_n-alkylsulfanyl-Ci-C_n-alkyl” refers to an alkyl radical (as mentioned above) substituted with a Ci-C_n-alkylsulfanyl group.

As used herein, the term “Ci-C_n-alkylsulfonyl” refers to a radical of the formula -S(O)2R_a wherein R_a is a Ci-Cn- alkyl radical as generally defined above.

As used herein, the term “Ci-C_n-alkylsulfonyl-Ci-C_n-alkyl” refers to an alkyl radical (as mentioned above) substituted with a Ci-C_n-alkylsulfonyl group.

As used herein, the term “Ci-C_n-alkoxyamino” refers to a radical of the formula R_aNH- wherein R_a is a Ci-C_n- alkoxy radical as generally defined above.

As used herein, the term “N,N-di(Ci-C_n-alkyl)amino” refers to a radical of the formula R_a(Rb)N- wherein R_a and Rb are the same or different Ci-C_n-alkyl radicals as generally defined above.

As used herein, the term “Ci-C_n-alkoxyamino-Ci-C_n-alkyl” refers to an alkyl radical (as mentioned above) substituted with a Ci-C_n-alkoxyamino group. Examples are methoxyamino methyl, or 1 -(methoxyamino)-1 - ethyl.

As used herein, the term “Ci-C_n-alkylcarbonyl” refers to a Ci-C_n-alkyl group linked through the carbon atom of a carbonyl (C=O) group. As used herein, the term “Ci-C_n-alkoxycarbonyl” refers to a Ci-C_n-alkoxy moiety linked through a carbon atom of a carbonyl (or C=O) group.

As used herein, the term “Ci-C_n-haloalkoxycarbonyl” refers to a Ci-C_n-alkoxycarbonyl radical respectively substituted with one or more halo atoms which may be the same or different.

As used herein, the term “Ci-C_n-alkoxycarbonyl-Ci-C_n-alkyl” refers to a Ci-C_n-alkyl radical (as mentioned above) substituted by a Ci-Cn-alkoxycarbonyl group.

As used herein, the term "Ci-C_n-alkylcarbonyloxy" refers to a radical of the formula -OC(O)R_a wherein R_a is a Ci-Cn-alkyl radical as generally defined above.

As used herein, the term “Ci-C_n-alkylcarbonyloxy-Ci-C_n-alkyl” refers to an alkyl radical (as mentioned above) substituted with a Ci-C_n-alkylcarbonyloxy group.

As used herein, the term "Ci-C_n-alkylcarbonylamino" refers to a radical of the formula R_aC(O)N(H)- wherein R_a is a Ci-Cn-alkyl radical as generally defined above.

As used herein, the term “Ci-C_n-alkylcarbonylamino-Ci-C_n-alkyl” refers to an alkyl radical (as mentioned above) substituted with a Ci-C_n-alkylcarbonylamino group.

As used herein, the term "Ci-C_n-alkoxycarbonylamino" refers to a radical of the formula R_aC(O)N(H)- wherein R_a is a Ci-Cn-alkoxy radical as generally defined above.

As used herein, the term “Ci-C_n-alkoxycarbonylamino-Ci-C_n-alkyl” refers to an alkyl radical (as mentioned above) substituted with a Ci-C_n-alkoxycarbonylamino group, amino

As used herein, the term “N,N-di(Ci-C_n-alkyl)aminocarbonyl” refers to a radical of the formula R_a(Rb)NC(O)- wherein R_a and Rb are the same or different Ci-C_n-alkyl radicals as generally defined above.

As used herein, the term " Cs-Cn-cycloalkyloxycarbonyl" refers to a radical of the formula -C(O)OR_a wherein R_a is a Cs-Cn-cycloalkyl radical as generally defined above.

As used herein, the term "phenyl-Ci-C_n-alkyl" refers to a Ci-C_n-alkyl radical substituted by a phenyl ring. Examples include benzyl. The phenyl-Ci-C_n-alkyl radical may be substituted on alkyl group and/or phenyl group.

As used herein, the term “heteroaryl" refers to a 5- or 6-membered aromatic monocyclic ring radical which contains 1 , 2, 3 or 4 heteroatoms individually selected from N, O or S. This ring radical will not comprise contiguous oxygen and sulfur atoms. Examples of heteroaryl include, but are not limited to, furanyl, pyrrolyl, thienyl, pyrazolyl, imidazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, triazolyl, tetrazolyl, pyrazinyl, pyridazinyl, pyrimidyl, or pyridyl. The term “heteroaryl-Ci-C_n-alkyl” refers to an Ci-C_n-alkyl radical respectively substituted by a heteroaryl group. The heteroaryl-Ci-C_n-alkyl radical may be substituted on heteroaryl, alkyl and/or cycloalkyl group as appropriate.

As used herein, the term "controlling" refers to reducing the number of pests, eliminating pests and/or preventing further pest damage such that damage to a plant or to a plant derived product is reduced. As used herein, the term "pest" refers to insects, and molluscs that are found in agriculture, horticulture, forestry, the storage of products of vegetable origin (such as fruit, grain, and timber); and those pests associated with the damage of man-made structures. The term pest encompasses all stages in the life cycle of the pest.

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

The term "controlling" when used in context of parasites in or on an animal refers to reducing the number of pests or parasites, eliminating pests or parasites and/or preventing further pest or parasite infestation.

The term "treating" when used in context of parasites in or on an animal refers to restraining, slowing, stopping, or reversing the progression or severity of an existing symptom or disease.

The term "preventing" when used in context of parasites in or on an animal refers to the avoidance of a symptom or disease developing in the animal.

The term "animal" when used in context of parasites in or on an animal may refer to a mammal and a nonmammal, such as a bird or fish. In the case of a mammal, it may be a human or non-human mammal. Nonhuman mammals include, but are not limited to, livestock animals and companion animals. Livestock animals include, but are not limited to, cattle, camellids, pigs, sheep, goats, and horses. Companion animals include, but are not limited to, dogs, cats, and rabbits.

The term "parasite" as used herein, refers to a pest which lives in or on the host animal and benefits by deriving nutrients at the host animal's expense. An "endoparasite" is a parasite which lives in the host animal. An "ectoparasite" is a parasite which lives on the host animal. Ectoparasites include, but are not limited to, acari, insects, and crustaceans (e.g., sea lice). The Acari (or Acarina) sub-class comprises ticks and mites. Ticks include, but are not limited to, members of the following genera: Rhipicaphalus, for example, Rhipicaphalus (Boophilus) microplus and Rhipicaphalus sanguineus; Amblyomrna; Dermacentor; Haemaphysalis; Hyalomma; Ixodes; Rhipicentor; Margaropus; Argas; Otobius; and Ornithodoros. Mites include, but are not limited to, members of the following genera: Chorioptes, for example Chorioptes bovis; Psoroptes, for example Psoroptes ovis; Cheyletiella; Dermanyssus; for example, Dermanyssus gallinae; Ortnithonyssus; Demodex, e.g., Demodex canis; Sarcoptes, e.g., Sarcoptes scabiei; and Psorergates. Insects include, but are not limited to, members of the orders: Siphonaptera, Diptera, Phthiraptera, Lepidoptera, Coleoptera and Homoptera. Members of the Siphonaptera order include, but are not limited to, Ctenocephalides felis and Ctenocephatides canis. Members of the Diptera order include, but are not limited to, Musca spp.; bot fly, e.g., Gasterophilus intestinalis and Oestrus ovis; biting flies; horse flies, e.g., Haematopota spp. and Tabunus spp.; haematobia, e.g., haematobia irritans; Stomoxys; Lucilia; midges; and mosquitoes. Members of the Phthiraptera class include, but are not limited to, blood sucking lice and chewing lice, e.g., Bovicola Ovis and Bovicola Bovis. The term "effective amount" when used in context of parasites in or on an animal refers to the amount or dose of the compound of the invention, or a salt thereof, which, upon single or multiple dose administration to the animal, provides the desired effect in or on the animal. The effective amount can be readily determined by the attending diagnostician, as one skilled in the art, by the use of known techniques and by observing results obtained under analogous circumstances. In determining the effective amount a number of factors are considered by the attending diagnostician, including, but not limited to: the species of mammal; its size, age, and general health; the parasite to be controlled and the degree of infestation; the specific disease or disorder involved; the degree of or involvement or the severity of the disease or disorder; the response of the individual; the particular compound administered; the mode of administration; the bioavailability characteristics of the preparation administered; the dose regimen selected; the use of concomitant medication; and other relevant circumstances.

As used herein, the term "effective amount" refers to the amount of the compound, or a salt thereof, which, upon single or multiple applications provides the desired effect.

An effective amount is readily determined by the skilled person in the art, by the use of known techniques and by observing results obtained under analogous circumstances. In determining the effective amount, a number of factors are considered including, but not limited to the type of plant or derived product to be applied; the pest to be controlled & its lifecycle; the particular compound applied; the type of application; and other relevant circumstances.

Unless otherwise stated, structures depicted herein are also meant to include all isomeric (e.g., enantiomeric, diastereomeric, and geometric (or conformational)) forms of the structure; for example, the R and S configurations for each asymmetric center, Z and E double bond isomers, and Z and E conformational isomers. Therefore, single stereochemical isomers as well as enantiomeric, diastereomeric, and geometric (or conformational) mixtures of the present compounds are within the scope of the invention. Unless otherwise stated, all tautomeric forms of the compounds of the invention are within the scope of the invention. Additionally, unless otherwise stated, structures depicted herein are also meant to include compounds that differ only in the presence of one or more isotopically enriched atoms. For example, compounds having the present structures including the replacement of hydrogen by deuterium or tritium, or the replacement of a carbon by a ¹³C-enriched or ¹⁴C-enriched carbon are within the scope of this invention. Such compounds are useful, for example, as analytical tools, as probes in biological assays, or as therapeutic agents in accordance with the present invention.

Diastereomeric mixtures can be separated into their individual diastereomers based on their physical chemical differences by methods known to those skilled in the art, such as, for example, by chromatography and/or fractional crystallization. Enantiomers can be separated by converting the enantiomeric mixture into a diastereomeric mixture by reaction with an appropriate optically active compound (e.g., chiral auxiliary such as a chiral alcohol or Mosher’s acid chloride), separating the diastereomers and converting (e.g., hydrolyzing) the individual diastereomers to the corresponding pure enantiomers. Alternatively, a particular enantiomer of a compound of the present invention may be prepared by asymmetric synthesis. Still further, where the molecule contains a basic functional group (such as amino) or an acidic functional group (such as carboxylic acid) diastereomeric salts are formed with an appropriate optically active acid or base, followed by resolution of the diastereomers thus formed by fractional crystallization or chromatographic means known in the art, and subsequent recovery of the pure enantiomers.

Individual stereoisomers of the compounds of the invention may, for example, be substantially free of other isomers, or may be admixed, for example, as racemates or with all other, or other selected, stereoisomers. Chiral center(s) in a compound of the present invention can have the S or R configuration as defined by the IUPAC 1974 Recommendations. Further, to the extent a compound described herein may exist as an atropisomer (e.g., substituted biaryls), all forms of such atropisomer are considered part of this invention.

Chemical names, common names, and chemical structures may be used interchangeably to describe the same structure. If a chemical compound is referred to using both a chemical structure and a chemical name, and an ambiguity exists between the structure and the name, the structure predominates. It should also be noted that any carbon as well as heteroatom with unsatisfied valences in the text, schemes, examples, and tables herein is assumed to have the sufficient number of hydrogen atom(s) to satisfy the valences.

The terms “a” and “an” as used herein mean “one or more” and include the plural unless the context is inappropriate.

Unless specified otherwise, the term “about” refers to within ±10% of the stated value. The invention encompasses embodiments where the value is within ±9%, ±8%, ±7%, ±6%, ±5%, ±4%, ±3%, ±2%, or ±1 % of the stated value.

As used herein, the term “room temperature” or “RT” or “rt” or “ambient temperature” refer to a temperature of about 15°C to about 35°C. For example, rt can refer to a temperature of about 20°C to about 30°C.

The following list provides definitions, including preferred definitions, for substituents R¹, R², R³, R⁴, R⁵, R⁶, R⁷, and R⁸ with reference to the compounds of formula (I) of the present invention. For any one of these substituents, any of the definitions given below may be combined with any definition of any other substituent given below or elsewhere in this document.

In one embodiment of the invention, R¹ is selected from hydrogen, Ci-C4-alkyl, Ci-C4-haloalkyl, C3-C6- cycloalkyl, Cs-Ce-halocycloalkyl, cyano-Ci-C4-alkyl, C3-C6-cycloalkyl-Ci-C4-alkyl, cyano-Cs-Ce-cycloalkyl, C1- C4-alkoxy, Ci-C4-haloalkoxy, C2-C4-alkynyloxy, Ci-C4-alkoxy-Ci-C4-alkyl, Ci-C4-alkoxy-Ci-C4-alkoxy, C3-C6- cycloalkyl-Ci-C4-alkoxy, Cs-Ce-cycloalkyloxy, N-(Ci-C4-alkyl)amino, N-(C3-C6-cycloalkyl)amino, N,N-di(Ci-C4- alkyl)amino, Ci-C4-alkoxyamino-Ci-C4-alkyl, Ci-C4-alkoxyimino, Ci-C4-alkylsulfonyl-Ci-C4-alkyl, C1-C4- alkylsulfanyl-Ci-C4-alkyl, Ci-C4-alkoxycarbonyl-Ci-C4-alkyl, Ci-C4-alkylcarbonyloxy-Ci-C4-alkyl, C1-C4- alkylcarbonylamino-Ci-C4-alkyl, Ci-C4-alkoxycarbonylamino-Ci-C4-alkyl, phenoxy-Ci-C4-alkyl, phenoxy, C5- Cs-bicycloalkyl, 3-, 4-, 5- or 6-membered heterocycloalkyl, phenyl, phenyl-Ci-C4-alkyl, 5- or 6-membered heteroaryl, or 5- or 6-membered heteroaryl-Ci-Cs-alkyl; wherein any of said 3-, 4-, 5- or 6-membered heterocycloalkyl contains 1 or 2 heteroatoms or groups individually selected from N, O, S, S=O, or SO2, with the proviso that no more than one is O, S, S=O or SO2; wherein any of said 5- or 6-membered heteroaryl and heteroary l-Ci-Cs-alkyl contains 1 , 2, 3 or 4 heteroatoms individually selected from N, S, or O, with the proviso that no more than one is O or S; wherein any of said Cs-Ce-cycloalkyl, and 3-, 4-, 5- or 6-membered heterocycloalkyl are unsubstituted or substituted by 1 , 2 or 3 substituents independently selected from halogen, cyano, Ci-Cs-alkyl, Ci-Cs-haloalkyl, or Cs-Ce-cycloalkyl; and wherein any of said phenyl, said 5- or 6-membered heteroaryl and heteroaryl-Ci-Cs-alkyl are unsubstituted or substituted by 1 , 2 or 3 substituents independently selected from halogen, cyano, Ci-C4-alkyl, Ci-C4-haloalkyl, or Ci-C4-alkoxy.

In one embodiment of the invention, R¹ is selected from Ci-C4-alkyl, Ci-C4-haloalkyl, Cs-Ce-cycloalkyl, C3-C6- halocycloalkyl, cyano-Ci-C4-alkyl, C3-C6-cycloalkyl-Ci-C4-alkyl, cyano-Cs-Ce-cycloalkyl, Ci-C4-alkoxy, C1-C4- haloalkoxy, C2-C4-alkynyloxy, Ci-C4-alkoxy-Ci-C4-alkyl, Ci-C4-alkoxy-Ci-C4-alkoxy, C3-Ce-cycloalkyl-Ci-C4- alkoxy, Cs-Ce-cycloalkyloxy, N,N-di(Ci-C4-alkyl)amino, Ci-C4-alkoxyamino-Ci-C4-alkyl, Ci-C4-alkoxyimino, C1- C4-alkylsulfonyl-Ci-C4-alkyl, Ci-C4-alkylsulfanyl-Ci-C4-alkyl, Ci-C4-alkoxycarbonyl-Ci-C4-alkyl, C1-C4- alkylcarbonyloxy-Ci-C4-alkyl, Ci-C4-alkylcarbonylamino-Ci-C4-alkyl, Ci-C4-alkoxycarbonylamino-Ci-C4-alkyl, phenoxy-Ci-C4-alkyl, C4-C8-bicycloalkyl, 3-, 4-, 5- or 6-membered heterocycloalkyl, phenyl-Ci-C4-alkyl, or 5- or 6-membered heteroaryl-Ci-Cs-alkyl; wherein any of said 3-, 4-, 5- or 6-membered heterocycloalkyl contains 1 or 2 heteroatoms or groups individually selected from N, O, S, S=O, or SO2, with the proviso that no more than one is O, S, S=O or SO2; wherein any of said 5- or 6-membered heteroaryl contains 1 , 2, 3 or 4 heteroatoms individually selected from N, S, or O, with the proviso that no more than one is O or S; wherein any of said Cs- Ce-cycloalkyl, and 3-, 4-, 5- or 6-membered heterocycloalkyl are unsubstituted or substituted by 1 , 2 or 3 substituents independently selected from halogen, cyano, Ci-Cs-alkyl, Ci-Cs-haloalkyl, or Cs-Ce-cycloalkyl; and wherein any of said phenyl and said 5- or 6-membered heteroaryl are unsubstituted or substituted by 1 , 2 or 3 substituents independently selected from halogen, cyano, Ci-C4-alkyl, Ci-C4-haloalkyl, or Ci-C4-alkoxy.

In another embodiment of the invention, R¹ is selected from Ci-C4-alkyl, Ci-Cs-haloalkyl, Cs-Ce-cycloalkyl, C3- Ce-halocycloalkyl, cyano-Ci-Cs-alkyl, Cs-Ce-cycloalkyl-Ci-Cs-alkyl, cyano-Cs-Ce-cycloalkyl, Ci-Cs-alkoxy, C1- Cs-haloalkoxy, C2-C3-alkynyloxy, Ci-Cs-alkoxy-Ci-Cs-alkyl, Ci-Cs-alkoxy-Ci-Cs-alkoxy, Cs-Ce-cycloalkyl-Ci-Cs- alkoxy, Cs-Ce-cycloalkyloxy, N,N-di(Ci-C3-alkyl)amino, Ci-Cs-alkoxyamino-Ci-Cs-alkyl, Ci-Cs-alkylsulfonyl-Ci- Cs-alkyl, Ci-Cs-alkylsulfanyl-Ci-Cs-alkyl, Ci-Cs-alkoxyimino, Ci-Cs-alkoxycarbonyl-Ci-Cs-alkyl, C1-C3- alkylcarbonyloxy-Ci-Cs-alkyl, Ci-Cs-alkylcarbonylamino-Ci-Cs-alkyl, Ci-Cs-alkoxycarbonylamino-Ci-Cs-alkyl, phenoxy-Ci-Cs-alkyl, C4-C8-bicycloalkyl, 3-, 4-, 5- or 6-membered heterocycloalkyl, phenyl-Ci-C2-alkyl, or 5- or 6-membered heteroaryl-Ci-C2-alkyl; wherein any of said 3-, 4-, 5- or 6-membered heterocycloalkyl contains 1 or 2 heteroatoms or groups individually selected from N, O, S, S=O, or SO2, with the proviso that no more than one is O, S, S=O or SO2; wherein any of said 5- or 6-membered heteroaryl contains 1 , 2, 3 or 4 heteroatoms individually selected from N, S or O, with the proviso that no more than one is O or S; wherein any of said C3- Ce-cycloalkyl and 3-, 4-, 5- or 6-membered heterocycloalkyl are unsubstituted or substituted by 1 , or 2 substituents independently selected from halogen, cyano, Ci-Cs-alkyl, Ci-Cs-haloalkyl, or Cs-Ce-cycloalkyl; and wherein any of said phenyl, and 5- or 6-membered heteroaryl are unsubstituted or substituted by 1 , or 2 substituents independently selected from halogen, cyano, Ci-Cs-alkyl, Ci-Cs-haloalkyl, or Ci-Cs-alkoxy. Preferably R¹ is Ci-C4-alkyl, Ci-Cs-haloalkyl, Cs-Ce-cycloalkyl, Cs-Ce-halocycloalkyl, cyano-Ci-C2-alkyl, C3-C6- cycloalkyl-Ci-C2-alkyl, cyano-Cs-Ce-cycloalkyl, Ci-Cs-alkoxy, Ci-C2-haloalkoxy, C2-C3-alkynyloxy, C1-C2- alkoxy-Ci-Cs-alkyl, Ci-C2-alkoxy-Ci-C2-alkoxy, C3-C6-cycloalkyl-Ci-C2-alkoxy, Cs-Ce-cycloalkyloxy, N,N-di(Ci- C2-alkyl)amino, Ci-C2-alkoxyamino-Ci-C2-alkyl, Ci-C2-alkylsulfonyl-Ci-C2-alkyl, Ci-C2-alkylsulfanyl-Ci-C2- alkyl, Ci-C2-alkoxyimino, Ci-C2-alkoxycarbonyl-Ci-C2-alkyl, Ci-C2-alkylcarbonyloxy-Ci-C2-alkyl, C1-C2- alkylcarbonylamino-Ci-C2-alkyl, Ci-C2-alkoxycarbonylamino-Ci-C2-alkyl, phenoxy-Ci-C2-alkyl, C4-C8- bicycloalky I, 4-, 5-, or 6-membered heterocycloalkyl, phenyl-Ci-C2-alkyl, or 5- or 6-membered heteroaryl-Ci- C2-alkyl; wherein any of said 4-, 5-, or 6-membered heterocycloalkyl contains one heteroatom or one group selected from N, O, S, S=O, or SO2; wherein any of said 5- or 6-membered heteroaryl contains one heteroatom selected from N, S or O, or 2 to 4 nitrogens, wherein said Cs-Ce-cycloalkyl is unsubstituted or substituted by 1 , or 2 substituents independently selected from cyano, or Ci-Cs-alkyl; and wherein said phenyl and 5- or 6- membered heteroaryl are unsubstituted or substituted by 1 , or 2 substituents independently selected from halogen, cyano, Ci-Cs-alkyl, Ci-C2-haloalkyl, or Ci-Cs-alkoxy.

In one embodiment, R¹ is Ci-C4-alkyl, Ci-Cs-haloalkyl, Cs-Ce-cycloalkyl, C3-C6-cycloalkyl-Ci-C2-alkyl, C3-C6- halocycloalkyl, cyano-Ci-C2-alkyl, Ci-Cs-alkoxy, Ci-C2-haloalkoxy, Ci-C2-alkoxy-Ci-C3-alkyl, C3-C6- cycloalkyloxy, C3-C6-cycloalkyl-Ci-C2-alkoxy, Ci-C2-alkylsulfonyl-Ci-C2-alkyl, N,N-di(Ci-C2-alkyl)amino, C1-C2- alkylcarbonylamino-Ci-C2-alkyl, phenoxy-Ci-C2-alkyl, 5-membered heterocycloalkyl, phenyl-Ci-C2-alkyl, or 5- membered heteroaryl-Ci-C2-alkyl; wherein said 5-membered heterocycloalkyl contains one heteroatom or one group selected from N, O, S, S=O, or SO2; wherein said 5-membered heteroaryl contains one heteroatom selected from N, S or O, or 2 to 4 nitrogens; and wherein said phenyl is unsubstituted or substituted by 1 , or 2 substituents independently selected from chloro or fluoro.

In one embodiment, R¹ is is Ci-C4-alkyl, Ci-Cs-haloalkyl, Cs-Ce-cycloalkyl, C3-C6-cycloalkyl-Ci-C2-alkyl, C3-C6- halocycloalkyl, cyano-Ci-C2-alkyl, Ci-Cs-alkoxy, Ci-C2-haloalkoxy, Ci-C2-alkoxy-Ci-C3-alkyl, C3-C6- cycloalkyloxy, C3-C6-cycloalkyl-Ci-C2-alkoxy, Ce-Cs-bicycloalkyl, wherein said Cs-Ce-cycloalkyl is unsubstituted or substituted by 1 , 2 or 3 substituents independently selected from halogen, cyano, Ci-Cs-alkyl, or Ci-Cs- haloalkyl, in particular cyano and methyl.

In one embodiment, R¹ is selected from Ci-C4-alkyl, Ci-C4-haloalkyl, Cs-Ce-cycloalkyl, Ci-Cs-alkoxy, or C1-C3- haloalkoxy.

More preferably R¹ is selected from Ci-C4-alkyl, Ci-Cs-haloalkyl, Cs-Ce-cycloalkyl, Cs-Ce-halocycloalkyl, cyano- Ci-C2-alkyl, cyano-Cs-Ce-cycloalkyl, Ci-Cs-alkoxy, Ci-C2-haloalkoxy, C2-C3-alkynyloxy, Ci-C2-alkoxy-Ci-C3- alkyl, Ci-C2-alkoxy-Ci-C2-alkoxy, Cs-Ce-cycloalkyl-Ci-Cs-alkoxy, Cs-Ce-cycloalkyloxy, N,N-di(Ci-C2- alkyl)amino, Ci-C2-alkoxyamino-Ci-C2-alkyl, Ci-C2-alkylsulfonyl, Ci-C2-alkyl, Ci-C2-alkylsulfanyl-Ci-C2-alkyl, Ci-C2-alkoxyimino, Ci-C2-alkoxycarbonyl-Ci-C2-alkyl, Ci-C2-alkylcarbonyloxy-Ci-C2-alkyl, C1-C2- alkylcarbonylamino-Ci-C2-alkyl, Ci-C2-alkoxycarbonylamino-Ci-C2-alkyl, phenoxy-Ci-C2-alkyl, 4-, 5- or 6- membered heterocycloalkyl, phenyl-Ci-C2-alkyl, or 5- or 6-membered heteroaryl-Ci-C2-alkyl; wherein any of said 4-, 5-, or 6-membered heterocycloalkyl contains one heteroatom or one group selected from N, O, S, S=O, or SO2; wherein any of said 5-, or 6-membered heteroaryl contains one heteroatom selected from N, S or O, or 2 to 4 nitrogens, wherein any of said Cs-Ce-cycloalkyl is unsubstituted or substituted by 1 , or 2 substituents independently selected from cyano, or Ci-Cs-alkyl; and wherein said phenyl is unsubstituted or substituted by 1 , or 2 substituents independently selected from halogen.

Even more preferably R¹ is selected from Ci-C4-alkyl, Ci-Cs-haloalkyl, Cs-Ce-cycloalkyl, cyano-Ci-C2-alkyl, cyano-Cs-Ce-cycloalkyl, Ci-Cs-alkoxy, Ci-C2-haloalkoxy, C2-C3-alkynyloxy, Ci-C2-alkoxy-Ci-C3-alkyl, C3-C6- cycloalkyl-Ci-C4-alkoxy, Cs-Ce-cycloalkyloxy, N,N-di(Ci-C2-alkyl)amino, Ci-C2-alkoxyamino-Ci-C2-alkyl, C1-C2- alkylsulfonyl-Ci-C2-alkyl, Ci-C2-alkylsulfanyl-Ci-C2-alkyl, Ci-C2-alkoxyimino, Ci-C2-alkoxycarbonyl-Ci-C2-alkyl, Ci-C2-alkylcarbonyloxy-Ci-C2-alkyl, Ci-C2-alkylcarbonylamino-Ci-C2-alkyl, phenoxy-Ci-C4-alkyl, 5-membered heterocycloalkyl, phenyl-Ci-C2-alkyl, or 5-membered heteroaryl-Ci-C2-alkyl; wherein said 5-membered heterocycloalkyl contains one heteroatom or one group selected from N, O, S, S=O, or SO2; wherein said 5- membered heteroaryl contains one heteroatom selected from N, S or O, or 2 to 4 nitrogens; and wherein said phenyl is unsubstituted or substituted by 1 , or 2 substituents independently selected from chloro or fluoro.

Still even more preferably, R¹ is Ci-C4-alkyl, Ci-Cs-haloalkyl, Cs-Ce-cycloalkyl, C3-C6-cycloalkyl-Ci-C2-alkyl, C3- Ce-halocycloalkyl, cyano-Ci-C2-alkyl, Ci-Cs-alkoxy, Ci-C2-haloalkoxy, Ci-C2-alkoxy-Ci-C3-alkyl, C3-C6- cycloalkyloxy, C3-C6-cycloalkyl-Ci-C2-alkoxy, Ci-C2-alkylsulfonyl-Ci-C2-alkyl, N,N-di(Ci-C2-alkyl)amino, C1-C2- alkylcarbonylamino-Ci-C2-alkyl, phenoxy-Ci-C2-alkyl, 5-membered heterocycloalkyl, phenyl-Ci-C2-alkyl, or 5- membered heteroaryl-Ci-C2-alkyl; wherein said 5-membered heterocycloalkyl contains one heteroatom or one group selected from N, O, S, S=O, or SO2; wherein said 5-membered heteroaryl contains one heteroatom selected from N, S or O, or 2 to 4 nitrogens; and wherein said phenyl is unsubstituted or substituted by 1 , or 2 substituents independently selected from chloro or fluoro.

In another embodiment of the invention, R¹ is selected from Ci-C4-alkyl, Ci-C4-haloalkyl, Cs-Ce-cycloalkyl, cyano-Ci-C4-alkyl, cyano-Cs-Ce-cycloalkyl, Cs-Ce-cycloalkyl-Ci-Cs-alkyl, cyano-Cs-Ce-cycloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, C2-C4-alkynyloxy, C3-C6-cycloalkyl-Ci-C4-alkoxy, Cs-Ce-cycloalkyloxy, Ci-C4-alkoxy-Ci-C4- alkyl, Ci-C4-alkoxyamino-Ci-C4-alkyl, Ci-C4-alkylsulfonyl-Ci-C4-alkyl, Ci-C4-alkylsulfanyl-Ci-C4-alkyl, C1-C4- alkylcarbonyloxy-Ci-C4-alkyl, Ci-C4-alkylcarbonylamino-Ci-C4-alkyl, 5- or 6-membered heterocycloalkyl, phenyl-Ci-Cs-alkyl, or 5- or 6-membered heteroaryl-Ci-C2-alkyl. Preferably, R¹ is Ci-C4-alkyl, Ci-Cs-haloalkyl, Cs-Ce-cycloalkyl, cyano-Ci-Cs-alkyl, Cs-Ce-cycloalkyl-Ci-Cs-alkyl, cyano-Cs-Ce-cycloalkyl, Ci-Cs-alkoxy, C1-C3- haloalkoxy, C2-C3-alkynyloxy, Cs-Ce-cycloalkyloxy, Ci-Cs-alkoxy-Ci-Cs-alkyl, or Ci-Cs-alkylsulfonyl-Ci-Cs-alkyl. More preferably, R¹ is Ci-C4-alkyl, Ci-C4-haloalkyl, Cs-Ce-cycloalkyl, cyano-Ci-Cs-alkyl, Ci-C4-alkoxy, C1-C3- alkoxy-Ci-Cs-alkyl, Ci-Cs-haloalkoxy, or Ce-Cs-bicycloalkyl, wherein said Cs-Ce-cycloalkyl is unsubstituted or substituted by 1 , 2 or 3 substituents independently selected from halogen, cyano, Ci-Cs-alkyl, or Ci-Cs- haloalkyl, in particular cyano and methyl. More preferably, R¹ is Ci-C4-alkyl, Ci-C4-haloalkyl, Cs-Ce-cycloalkyl, cyano-Ci-Cs-alkyl, Ci-C4-alkoxy, or Ci-Cs-haloalkoxy. Even more preferably, R¹ is Ci-C4-alkyl, Cs-Ce- cycloalkyl, or Ci-Cs-alkoxy.

In one embodiment of the invention, R² is selected from hydrogen, Ci-C4-alkyl, Ci-C4-alkoxy, Ci-C4-alkoxy-Ci- C4-alkyl, cyano-Ci-C4-alkyl, Ci-C4-alkylcarbonyl, or Ci-C4-alkoxycarbonyl. In another embodiment of the invention, R² is selected from hydrogen, Ci-Cs-alkyl, Ci-Cs-alkoxy, Ci-C2-alkoxy-Ci-Cs-alkyl, cyano-Ci-Cs-alkyl, Ci-C2-alkylcarbonyl, or Ci-C2-alkoxycarbonyl. Preferably R² is hydrogen, Ci-Cs-alkyl, Ci-C2-alkylcarbonyl, or Ci-C2-alkoxycarbonyl. More preferably R² is hydrogen, or methyl. Even more preferably R² is hydrogen.

In one embodiment of the invention, R³ is selected from hydrogen, or Ci-Cs-alkyl. Preferably R³ is hydrogen, methyl, or ethyl. More preferably R³ is hydrogen, or methyl. In one embodiment R³ is hydrogen. In another embodiment R³ is methyl.

In one embodiment of the invention, R⁴ is selected from hydrogen, halogen, or Ci-Cs-alkyl. Preferably R⁴ is hydrogen, chlorine, fluorine, or methyl. Preferably, R⁴ is hydrogen or halogen. More preferably, R⁴ is hydrogen, chlorine, or fluorine. Even more preferably, R⁴ is hydrogen or fluorine.

In one embodiment of the invention, R⁵ and R⁶ are independently selected from hydrogen, or Ci-Cs-alkyl; or R⁵ and R⁶ together with the carbon to which they are attached represent a Cs-Cs-cycloalkyl group. Preferably R⁵ and R⁶ are independently selected from hydrogen, or methyl; or R⁵ and R⁶ together with the carbon to which they are attached represent a cyclopropyl group. In one embodiment, R⁵ is methyl and R⁶ is hydrogen, or R⁵ is methyl and R⁶ is methyl, or R⁵ and R⁶ together with the carbon to which they are attached represent a cyclopropyl group.

In one embodiment of the invention, R⁵ is selected from hydrogen, or Ci-Cs-alkyl. Preferably R⁵ is hydrogen or methyl. More preferably R⁵ is methyl.

In one embodiment of the invention, R⁶ is selected from hydrogen, or Ci-Cs-alkyl. Preferably R⁶ is hydrogen or methyl. More preferably R⁶ is hydrogen.

In another embodiment of the invention, R⁵ and R⁶ together with the carbon to which they are attached represent a Cs-Cs-cycloalkyl group. Preferably R⁵ and R⁶ together with the carbon to which they are attached represent a cyclopropyl group.

In one embodiment of the invention, R⁷ is selected from Ci-C4-alkyl, Ci-C4-haloalkyl, Cs-Ce-cycloalkyl, phenyl, or 5- or 6-membered heteroaryl; wherein any of said Cs-Ce-cycloalkyl is unsubstituted or substituted by 1 , 2 or 3 substituents independently selected from halogen, cyano, Ci-Cs-alkyl, or Ci-Cs-haloalkyl; wherein any of said 5- or 6-membered heteroaryl contains 1 or 2 heteroatoms individually selected from N, S or O, with the proviso that no more than one is O or S; and wherein any of said phenyl, and said 5- or 6-membered heteroaryl are unsubstituted or substituted by 1 , 2 or 3 substituents independently selected from halogen, cyano, Ci-C4-alkyl, Ci-C4-haloalkyl, or Ci-C4-alkoxy.

In another embodiment of the invention, R⁷ is selected from Ci-C4-alkyl, Ci-C4-haloalkyl, Cs-Ce-cycloalkyl, phenyl or 5- or 6-membered heteroaryl; wherein any of said Cs-Ce-cycloalkyl is unsubstituted or substituted by 1 , or 2 substituents independently selected from halogen, cyano, Ci-Cs-alkyl or Ci-Cs-haloalkyl; wherein any of said 5- or 6-membered heteroaryl contains 1 or 2 heteroatoms individually selected from N, S or O, with the proviso that no more than one is O or S; and wherein any of said phenyl, and said 5- or 6-membered heteroaryl are unsubstituted or substituted by 1 , or 2 substituents independently selected from halogen, cyano, Ci-Cs- alkyl, Ci-Cs-haloalkyl, or Ci-Cs-alkoxy. Preferably R⁷ is selected from Ci-C4-alkyl, Ci-C4-haloalkyl, Cs-Ce-cycloalkyl, phenyl, or 5- or 6-membered heteroaryl; wherein any of said 5- or 6-membered heteroaryl contains one heteroatom selected from N, S or O; and wherein any of said phenyl, and said 5- or 6-membered heteroaryl are unsubstituted or substituted by 1 , or 2 substituents independently selected from halogen, cyano, Ci-Cs-alkyl, Ci-Cs-haloalkyl, or Ci-Cs-alkoxy.

More preferably R⁷ is Ci-C2-haloalkyl, or Cs-Ce-cycloalkyl. Even more preferably R⁷ is dichloromethyl, difluoromethyl, trifluoromethyl, or cyclopropyl. Still even more preferably R⁷ is dichloromethyl, difluoromethyl, or trifluoromethyl. Most preferably R⁷ is tri fluoro methyl.

In another embodiment of the invention, R⁷ is Ci-C2-haloalkyl. Preferably R⁷ is dichloromethyl, difluoromethyl, or trifluoromethyl. Even more preferably R⁷ is trifluoromethyl.

In one embodiment of the invention, R⁸ is selected from hydrogen, Ci-C4-alkyl, Ci-C4-alkoxy, Ci-C4-alkoxy-Ci- C4-alkyl, cyano-Ci-C4-alkyl, Ci-C4-alkylcarbonyl, Ci-C4-alkoxycarbonyl, Ci-C4-haloalkoxycarbonyl, C1-C4- alkylcarbonyloxy-Ci-C4-alkyl, N,N-di(Ci-C4-alkyl)aminocarbonyl, or Cs-Ce-cycloalkyloxycarbonyl.

In another embodiment of the invention, R⁸ is selected from hydrogen, Ci-Cs-alkyl, Ci-Cs-alkoxy, Ci-Cs-alkoxy- Ci-Cs-alkyl, cyano-Ci-Cs-alkyl, Ci-Cs-alkylcarbonyl, Ci-Cs-alkoxycarbonyl, Ci-C2-haloalkoxycarbonyl, C1-C3- alkylcarbonyloxy-Ci-C2-alkyl, N,N-di(Ci-C2-alkyl)aminocarbonyl, or Cs-Ce-cycloalkyloxycarbonyl.

Preferably R⁸ is hydrogen, Ci-C2-alkyl, Ci-C2-alkoxy-Ci-C2-alkyl, cyano-Ci-C2-alkyl, Ci-Cs-alkylcarbonyl, C1- Cs-alkoxycarbonyl, Ci-C2-haloalkoxycarbonyl, Ci-C3-alkylcarbonyloxy-Ci-C2-alkyl, N,N-di(Ci-C2- alkyl)aminocarbonyl, or Cs-Ce-cycloalkyloxycarbonyl.

More preferably R⁸ is hydrogen, methyl, ethyl, methoxymethyl, ethoxymethyl, cyanomethyl, acetyl, 2- methylpropanoyl, methoxycarbonyl, isopropoxycarbonyl, 2,2-difluoroethoxycarbonyl, acetoxy methyl, 2- methylpropanoyloxy methyl, dimethylcarbamoyl, or cyclopropoxycarbonyl.

Even more preferably R⁸ is hydrogen or methoxymethyl. Still even more preferably R⁸ is hydrogen.

In another embodiment of the invention, R⁸ is selected from hydrogen, Ci-Cs-alkyl, Ci-Cs-alkoxy, Ci-Cs-alkoxy- Ci-Cs-alkyl, Ci-Cs-alkylcarbonyl, or Ci-Cs-alkoxycarbonyl. Preferably R⁸ is hydrogen, Ci-Cs-alkoxy, C1-C3- alkoxy-Ci-Cs-alkyl, or Ci-Cs-alkylcarbonyl. More preferably, R⁸ is hydrogen, Ci-Cs-alkoxy-Ci-Cs-alkyl or Ci-Cs- alkylcarbonyl. Even more preferably R⁸ is hydrogen, methoxy methyl, or methoxycarbonyl. Still even more preferably R⁸ is hydrogen.

The present invention, accordingly, makes available a compound of formula (I) having R¹, R², R³, R⁴, R⁵, R⁶, R⁷, and R⁸, as defined above in all combinations / each permutation.

Embodiments according to the invention are provided as set out below.

In one embodiment, in a compound of formula (I) according to the present invention R² is hydrogen, Ci-Cs- alkyl, Ci-C2-alkylcarbonyl, or Ci-C2-alkoxycarbonyl; R³ is hydrogen or methyl; R⁴ is hydrogen or halogen; R⁵ and R⁶ are independently selected from hydrogen, or methyl; or R⁵ and R⁶ together with the carbon to which they are attached represent a cyclopropyl group; and R¹, R⁷ and R⁸ are as defined above for compounds of formula (I). In one embodiment, in a compound of formula (I) according to the present invention R² is hydrogen, C1-C3- alkyl, Ci-C2-alkylcarbonyl, or Ci-C2-alkoxycarbonyl; R³ is hydrogen; R⁴ is hydrogen or fluorine; R⁵ and R⁶ are independently selected from hydrogen, or methyl; or R⁵ and R⁶ together with the carbon to which they are attached represent a cyclopropyl group; and R¹, R⁷ and R⁸ are as defined above for compounds of formula (I).

In one embodiment, in a compound of formula (I) according to the present invention R² is hydrogen; R³ is hydrogen; R⁴ is hydrogen or fluorine; R⁵ and R⁶ are independently selected from hydrogen, or methyl; or R⁵ and R⁶ together with the carbon to which they are attached represent a cyclopropyl group; and R¹, R⁷ and R⁸ are as defined above for compounds of formula (I).

In one embodiment, in a compound of formula (I) according to the present invention R² is hydrogen, Ci-Cs- alkyl, Ci-C2-alkylcarbonyl, or Ci-C2-alkoxycarbonyl; R³ is hydrogen or methyl; R⁴ is hydrogen or halogen; R⁵ and R⁶ are independently selected from hydrogen, or methyl; or R⁵ and R⁶ together with the carbon to which they are attached represent a cyclopropyl group; R⁷ is Ci-C2-haloalkyl; R⁸ is hydrogen, Ci-Cs-alkyl, C1-C3- alkoxy, Ci-Cs-alkoxy-Ci-Cs-alkyl, Ci-Cs-alkylcarbonyl, or Ci-Cs-alkoxycarbonyl; and R¹ is as defined above for compounds of formula (I).

In one embodiment, in a compound of formula (I) according to the present invention R² is hydrogen, C1-C3- alkyl, Ci-C2-alkylcarbonyl, or Ci-C2-alkoxycarbonyl; R³ is hydrogen; R⁴ is hydrogen or fluorine; R⁵ and R⁶ are independently selected from hydrogen, or methyl; or R⁵ and R⁶ together with the carbon to which they are attached represent a cyclopropyl group; R⁷ is Ci-C2-haloalkyl; R⁸ is hydrogen, Ci-Cs-alkyl, Ci-Cs-alkoxy, C1- Cs-alkoxy-Ci-Cs-alkyl, Ci-Cs-alkylcarbonyl, or Ci-Cs-alkoxycarbonyl; and R¹ is as defined above for compounds of formula (I).

In one embodiment, in a compound of formula (I) according to the present invention, R² is hydrogen; R³ is hydrogen; R⁴ is hydrogen or fluorine; R⁵ and R⁶ are independently selected from hydrogen, or methyl; or R⁵ and R⁶ together with the carbon to which they are attached represent a cyclopropyl group; R⁷ is Ci-C2-haloalkyl; R⁸ is hydrogen, Ci-Cs-alkyl, Ci-Cs-alkoxy, Ci-Cs-alkoxy-Ci-Cs-alkyl, Ci-Cs-alkylcarbonyl, or Ci-Cs- alkoxycarbonyl; and R¹ is as defined above for compounds of formula (I).

In one embodiment, in a compound of formula (I) according to the present invention R¹ is Ci-C4-alkyl, C1-C3- haloalky I, Cs-Ce-cycloalkyl, Cs-Ce-halocycloalkyl, cyano-Ci-C2-alkyl, Cs-Ce-cycloalkyl-Ci-Cs-alkyl, cyano-Cs-Ce- cycloalkyl, Ci-Cs-alkoxy, Ci-C2-haloalkoxy, C2-C3-alkynyloxy, Ci-C2-alkoxy-Ci-C3-alkyl, Ci-C2-alkoxy-Ci-C2- alkoxy, Cs-Ce-cycloalkyl-Ci-Cs-alkoxy, Cs-Ce-cycloalkyloxy, N,N-di(Ci-C2-alkyl)amino, Ci-C2-alkoxyamino-Ci- C2-alkyl, Ci-C2-alkylsulfonyl-Ci-C2-alkyl, Ci-C2-alkylsulfanyl-Ci-C2-alkyl, Ci-C2-alkoxyimino, C1-C2- alkoxycarbonyl-Ci-C2-alkyl, Ci-C2-alkylcarbonyloxy-Ci-C2-alkyl, Ci-C2-alkylcarbonylamino-Ci-C2-alkyl, C1-C2- alkoxycarbonylamino-Ci-C2-alkyl, phenoxy-Ci-C2-alkyl, C4-C8-bicycloalkyl, 4-, 5-, or 6-membered heterocycloalkyl, phenyl-Ci-C2-alkyl, or 5- or 6-membered heteroaryl-Ci-C2-alkyl; wherein any of said 4-, 5-, or 6-membered heterocycloalkyl contains one heteroatom or one group selected from N, O, S, S=O, or SO2; wherein any of said 5- or 6-membered heteroaryl contains one heteroatom selected from N, S or O, or 2 to 4 nitrogens, wherein said Cs-Ce-cycloalkyl is unsubstituted or substituted by 1 , or 2 substituents independently selected from cyano, or Ci-Cs-alkyl; and wherein said phenyl and 5- or 6-membered heteroaryl are unsubstituted or substituted by 1 , or 2 substituents independently selected from halogen, cyano, Ci-Cs-alkyl, Ci-C2-haloalkyl, or Ci-Cs-alkoxy; R² is hydrogen, Ci-Cs-alkyl, Ci-C2-alkylcarbonyl, or Ci-C2-alkoxycarbonyl; R³ is hydrogen or methyl; R⁴ is hydrogen or halogen; R⁵ and R⁶ are independently selected from hydrogen, or methyl; or R⁵ and R⁶ together with the carbon to which they are attached represent a cyclopropyl group; R⁷ is Ci-C2-haloalkyl; and R⁸ is hydrogen, Ci-Cs-alkyl, Ci-Cs-alkoxy, Ci-Cs-alkoxy-Ci-Cs-alkyl, Ci-Cs-alkylcarbonyl, or Ci-Cs-alkoxycarbonyl.

In one embodiment, in a compound of formula (I) according to the present invention R¹ is Ci-C4-alkyl, C1-C3- haloalkyl, Cs-Ce-cycloalkyl, cyano-Ci-Cs-alkyl, Cs-Ce-cycloalkyl-Ci-Cs-alkyl, cyano-Cs-Ce-cycloalkyl, Ci-Cs- alkoxy, Ci-Cs-haloalkoxy, C2-C3-alkynyloxy, Cs-Ce-cycloalkyloxy, Ci-Cs-alkoxy-Ci-Cs-alkyl, or C1-C3- alkylsulfonyl-Ci-Cs-alkyl; R² is hydrogen, Ci-Cs-alkyl, Ci-C2-alkylcarbonyl, or Ci-C2-alkoxycarbonyl; R³ is hydrogen or methyl; R⁴ is hydrogen or halogen; R⁵ and R⁶ are independently selected from hydrogen, or methyl; or R⁵ and R⁶ together with the carbon to which they are attached represent a cyclopropyl group; R⁷ is C1-C2- haloalkyl; and R⁸ is hydrogen, Ci-Cs-alkyl, Ci-Cs-alkoxy, Ci-Cs-alkoxy-Ci-Cs-alkyl, Ci-Cs-alkylcarbonyl, or Ci- Cs-alkoxy carbonyl.

In one embodiment, in a compound of formula (I) according to the present invention R¹ is Ci-C4-alkyl, C1-C3- haloalkyl, Cs-Ce-cycloalkyl, cyano-Ci-Cs-alkyl, Cs-Ce-cycloalkyl-Ci-Cs-alkyl, cyano-Cs-Ce-cycloalkyl, C1-C3- alkoxy, Ci-Cs-haloalkoxy, Cs-Cs-alkynyloxy, Cs-Ce-cycloalkyloxy, Ci-Cs-alkoxy-Ci-Cs-alkyl, or C1-C3- alkylsulfonyl-Ci-Cs-alkyl; R² is hydrogen, Ci-Cs-alkyl, Ci-C2-alkylcarbonyl, or Ci-C2-alkoxycarbonyl; R³ is hydrogen or methyl; R⁴ is hydrogen or halogen; R⁵ and R⁶ are independently selected from hydrogen, or methyl; or R⁵ and R⁶ together with the carbon to which they are attached represent a cyclopropyl group; R⁷ is C1-C2- haloalkyl; and R⁸ is hydrogen, Ci-Cs-alkyl, Ci-Cs-alkoxy, Ci-Cs-alkoxy-Ci-Cs-alkyl, Ci-Cs-alkylcarbonyl, or Ci- Cs-alkoxy carbonyl.

In one embodiment, in a compound of formula (I) according to the present invention R¹ is Ci-C4-alkyl, C1-C3- haloalkyl, Cs-Ce-cycloalkyl, cyano-Ci-Cs-alkyl, Cs-Ce-cycloalkyl-Ci-Cs-alkyl, cyano-Cs-Ce-cycloalkyl, C1-C3- alkoxy, Ci-Cs-haloalkoxy, Cs-Cs-alkynyloxy, Cs-Ce-cycloalkyloxy, Ci-Cs-alkoxy-Ci-Cs-alkyl, or C1-C3- alkylsulfonyl-Ci-Cs-alkyl; R² is hydrogen, Ci-Cs-alkyl, Ci-C2-alkylcarbonyl, or Ci-C2-alkoxycarbonyl; R³ is hydrogen; R⁴ is hydrogen or fluorine; R⁵ and R⁶ are independently selected from hydrogen, or methyl; or R⁵ and R⁶ together with the carbon to which they are attached represent a cyclopropyl group; R⁷ is Ci-C2-haloalkyl; and R⁸ is hydrogen, Ci-Cs-alkyl, Ci-Cs-alkoxy, Ci-Cs-alkoxy-Ci-Cs-alkyl, Ci-Cs-alkylcarbonyl, or C1-C3- alkoxy carbonyl.

In one embodiment, in a compound of formula (I) according to the present invention R¹ is Ci-C4-alkyl, C1-C3- haloalkyl, Cs-Ce-cycloalkyl, cyano-Ci-Cs-alkyl, Cs-Ce-cycloalkyl-Ci-Cs-alkyl, cyano-Cs-Ce-cycloalkyl, C1-C3- alkoxy, Ci-Cs-haloalkoxy, Cs-Cs-alkynyloxy, Cs-Ce-cycloalkyloxy, Ci-Cs-alkoxy-Ci-Cs-alkyl, or C1-C3- alkylsulfonyl-Ci-Cs-alkyl; R² is hydrogen, Ci-Cs-alkyl, Ci-C2-alkylcarbonyl, or Ci-C2-alkoxycarbonyl; R² is hydrogen; R³ is hydrogen; R⁴ is hydrogen or fluorine; R⁵ and R⁶ are independently selected from hydrogen, or methyl; or R⁵ and R⁶ together with the carbon to which they are attached represent a cyclopropyl group; R⁷ is Ci-C2-haloalkyl; and R⁸ is hydrogen, Ci-Cs-alkyl, Ci-Cs-alkoxy, Ci-Cs-alkoxy-Ci-Cs-alkyl, Ci-Cs-alkylcarbonyl, or Ci-Cs-alkoxycarbonyl.

In one embodiment, in a compound of formula (I) according to the present invention R¹ is Ci-C4-alkyl, C1-C3- haloalkyl, Cs-Ce-cycloalkyl, cyano-Ci-Cs-alkyl, Cs-Ce-cycloalkyl-Ci-Cs-alkyl, cyano-Cs-Ce-cycloalkyl, C1-C3- alkoxy, Ci-Cs-haloalkoxy, C2-C3-alkynyloxy, Cs-Ce-cycloalkyloxy, Ci-Cs-alkoxy-Ci-Cs-alkyl, or C1-C3- alkylsulfonyl-Ci-Cs-alkyl; R² is hydrogen, Ci-Cs-alkyl, Ci-C2-alkylcarbonyl, or Ci-C2-alkoxycarbonyl; R² is hydrogen; R³ is hydrogen; R⁴ is hydrogen or fluorine; R⁵ and R⁶ are independently selected from hydrogen, or methyl; or R⁵ and R⁶ together with the carbon to which they are attached represent a cyclopropyl group; R⁷ is Ci-C2-haloalkyl; and R⁸ is hydrogen, Ci-Cs-alkoxy, Ci-Cs-alkoxy-Ci-Cs-alkyl, or Ci-Cs-alkylcarbonyl.

Preferably, the compound according to formula (I) is selected from a compound listed in Tables A1 to A6, or Table P (below).

More preferably, the compound according to formula (I) is selected from a compound listed in Table P (below).

In one embodiment, the compounds of formula (I) are selected from the group consisting of

A/-[[2-cyano-4-fluoro-5-[(2S)-2-(trifluoromethylsulfonylamino)propoxy]phenyl]methyl]-2-fluoro-2-methyl- pro panamide;

A/-[[2-cyano-4-fluoro-5-[(2S)-2-(trifluoromethylsulfonylamino)propoxy]phenyl]methyl]-3-fluoro-propanamide;

A/-[[2-cyano-4-fluoro-5-[(2S)-2-(trifluoromethylsulfonylamino)propoxy]phenyl]methyl]-2,2-dimethyl- cyclopropanecarboxamide;

/V-[[2-cyano-4-fluoro-5-[(2S)-2-(trifluoromethylsulfonylamino)propoxy]phenyl]methyl]-1 -methyl- cyclobutanecarboxamide;

A/-[[2-cyano-4-fluoro-5-[(2S)-2-(trifluoromethylsulfonylamino)propoxy]phenyl]methyl]-2-methoxy-acetamide;

A/-[[2-cyano-4-fluoro-5-[(2S)-2-(trifluoromethylsulfonylamino)propoxy]phenyl]methyl]cyclobutene carboxamide;

(1 S,2S)-A/-[[2-cyano-4-fluoro-5-[(2S)-2-(trifluoromethylsulfonylamino)propoxy]phenyl]methyl]-2-methyl- cyclopropanecarboxamide;

A/-[[2-cyano-4-fluoro-5-[(2S)-2-(trifluoromethylsulfonylamino)propoxy]phenyl]methyl]-2,2-difluoro- pro panamide;

1-cyano-A/-[[2-cyano-4-fluoro-5-[(2S)-2-

(trifluoromethylsulfonylamino)propoxy]phenyl] methyl] cyclopropanecarboxamide;

A/-[[2-cyano-4-fluoro-5-[(2S)-2-(trifluoromethylsulfonylamino)propoxy]phenyl]methyl]bicyclo[1 .1.1]pentane-1- carboxamide; methyl A/-[[2-cyano-4-fluoro-5-[(2S)-2-(trifluoromethylsulfonylamino)propoxy]phenyl]methyl]carbamate; methyl A/-[(1 S)-2-[4-cyano-2-fluoro-5-[(propanoylamino)methy l]phenoxy]-1 -methy l-ethyl]-/V- (trifluoromethylsulfonyl)carbamate;

A/-[[2-cyano-4-fluoro-5-[(2S)-2- [methoxymethyl(trifluoromethylsulfonyl)amino]propoxy]phenyl]methyl]propenamide; and ethyl A/-[[2-cyano-4-fluoro-5-[(2S)-2-(trifluoromethylsulfonylamino)propoxy]phenyl]methyl]carbamate.

The compounds of formula (I) according to the present invention may possess at least two chiral centres at carbon atoms marked with a star (*) as outlined below in formula (l-a).

(l-a)

Accordingly, as already indicated, the compounds of formula (I) may exist in various diastereomeric forms, e.g., with (S,S)-, (S,R)-, (/?,/?)-, or (R,S)- configurations present at carbon atoms marked with a star (*) as in formula (l-a), respectively. In particular, each of these configurations may be evident for compounds of formula (I) in relation to the specific combinations of definitions for R¹, R², R³, R⁴, R⁵, R⁶, R⁷, and R⁸, for each compound described in Tables A1 to A6 or Table P (below).

The present invention in a further aspect provides a method of controlling parasites in or on an animal in need thereof comprising administering an effective amount of a compound of the first aspect. The present invention further provides a method of controlling ectoparasites on an animal in need thereof comprising administering an effective amount of a compound of formula (I) as defined om the first aspect. The present invention further provides a method for preventing and/or treating diseases transmitted by ectoparasites comprising administering an effective amount of a compound of formula (I) as defined in the first aspect, to an animal in need thereof.

Compounds of formula (I) can be prepared by those skilled in the art following known methods. More specifically compounds of formula (I), and intermediates therefor can be prepared as described below in the schemes and examples. Certain stereogenic centers have been left unspecified for the clarity and are not intended to limit the teaching of the schemes in any way.

The compounds of formula (I) according to the invention, wherein R¹, R², R³, R⁴, R⁵, R⁶, R⁷ and R⁸ are as defined for formula (I), can be obtained by transformation of a compound of formula (II), wherein R², R³, R⁴, R⁵, R⁶, R⁷ and R⁸ are as defined for compounds of formula (I), with an acid chloride or activated acylating agent of formula (III), wherein R¹ is as defined for compounds of formula (I), and G is as described below (Scheme 1). Scheme 1

As shown in Scheme 1 , compound (Illa) is activated to compounds of formula (III) by methods known to those skilled in the art and described for example in Tetrahedron 2005, 61 (46), 10827-10852. For example, when not commercially available, compounds of formula (III) where G is halogen are formed by treatment of compounds of formula (Illa) with for example, oxalyl chloride or thionyl chloride in the presence of catalytic quantities of dimethylformamide (DMF) in inert solvents such as dichloromethane (DCM) or tetra hydrofuran (THF) at temperatures between 25 and 170°C, preferably between 25 and 80°C. Treatment of (II) with compounds of formula (III), optionally in the presence of a base, e.g. TEA or pyridine leads to compounds of formula (I). Alternatively, compounds of formula (I) can be prepared by treatment of compounds of formula (Illa) with dicyclohexyl carbodiimide (DCC) or 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (EDC) to give the activated species (III), wherein G is G1 or G2, in an inert solvent, e.g. pyridine, or THF, optionally in the presence of a base, e.g. TEA, at temperatures between room temperature and 180°C. In addition, an acid of the formula (Illa) can also be activated by reaction with a coupling reagent such as propanephosphonic acid anhydride (T3P®) or O-(7-Aza-1-benzotriazolyl)-N,N,N’,N’-tetramethyluronium-hexafluorophosphat (HATU) to provide compounds of formula (III) wherein G is G3 and G4, as described for example in Synthesis 2013, 45, 1569, and J. prakt. Chem. 1998, 340, 581. Subsequent reaction with an amine of the formula (II) provides compounds of formula (I). Alternatively, compounds of formula (II) can be converted to compounds of formula (I) by reaction with an anhydride of formula (III) wherein G is G5, as described for example in WO 2010/100405.

The compounds of formula (I) according to the invention, wherein R¹, R², R³, R⁴, R⁵, R⁶, R⁷ and R⁸ are as defined for formula (I), can be obtained by transformation of a compound of formula (la), wherein R¹, R², R³, R⁴, R⁵, R⁶, and R⁷ are as defined for compounds of formula (I), with a compound of formula (IV), wherein R⁸ is as defined for compounds of formula (I), and Q is halogen, Q1 , Q2, or Q3 (Scheme 2). Scheme 2

As shown in Scheme 2, compounds (la) can be converted to compounds (I) by methods known to those skilled in the art and described for example in ACS Comb. Sci. 2016, 569; WO 2021/15372. For example, the reaction can be performed in organic solvent, such as DCM, DMF, or acetonitrile, in the presence of a base, such as potassium carbonate or TEA. Alternatively, the reaction can be performed with a reagent of formula (IVa). In this case the reaction can be performed in organic solvent, such as DCM, DMF, or acetonitrile, in the presence of a base, such as potassium carbonate or TEA and with the aid of a catalyst, such as 4- (Dimethylamino)pyridine as described for example in WO 2021/178885; Org. Process Res. Dev. 2014, 18, 205.

The compounds of formula (I), wherein R¹ , R², R³, R⁴, R⁵, R⁶, R⁷ and R⁸ are as defined for formula (I), can be obtained by transformation of a compound of formula (V), wherein R¹ , R², R³, R⁴, R⁵, R⁶, R⁷ and R⁸ are as defined for compounds of formula (I), and R⁹ is halogen (Scheme 3).

Scheme 3

As shown in scheme 3, compounds (V) can be converted to compounds (I) by means of methods known to those skilled in the art and described for example in US 20210078999, WO 2022/266162, WO 2012/102405. For example, the reaction can be performed in an organic solvent such as DMF, THF, DCM or dioxane, in the presence of a cyanide salt such as zinc(ll) cyanide or potassium hexacyanoferrate(ll), in the presence of an organometallic catalyst, such as allylpalladium chloride dimer or tris(dibenzylideneacetone)dipalladium, in the optional presence of a ligand such as 2-dicyclohexylphosphin-2',4',6'-triisopropylbiphenyl, at a temperature range between 0°C and 150°C.

The compounds of formula (V) according to the invention, wherein R¹, R², R³, R⁴, R⁵, R⁶, R⁷ and R⁸ are as defined for compounds of formula (I), and R⁹ is halogen, can be obtained by transformation of a compound of formula (VI), wherein R², R³, R⁴, R⁵, R⁶, R⁷ and R⁸ are as defined for compounds of formula (I), and R⁹ is halogen, with an acid chloride or activated acylating agent of formula (III), wherein R¹ is as defined for compounds of formula (I), and wherein G is as defined as in Scheme 1 (Scheme 4).

Scheme 4

As shown in Scheme 4, compound (Illa), is activated to compounds of formula (III) by methods known to those skilled in the art and described for example in Tetrahedron 2005, 61 (46), 10827-10852. For example, when not commercially available, compounds of formula (III) where G is halogen are formed by treatment of compounds of formula (Illa) with for example, oxalyl chloride or thionyl chloride in the presence of catalytic quantities of DMF in inert solvents such as DCM or THF, at temperatures between 25 and 170°C, preferably between 25 and 80°C. Treatment of (VI) with compounds of formula (III), optionally in the presence of a base, e.g. TEA or pyridine leads to compounds of formula (V). Alternatively, compounds of formula (V) can be prepared by treatment of compounds of formula (Illa) with dicyclohexyl carbodiimide (DCC) or 1 -ethyl-3-(3- dimethylaminopropyl)carbodiimide (EDC) to give the activated species (III), wherein G is G1 or G2, in an inert solvent, e.g. pyridine, or THF optionally in the presence of a base, e.g. TEA, at temperatures between rt and 180°C. In addition, an acid of the formula (Illa) can also be activated by reaction with a coupling reagent such as propanephosphonic acid anhydride (T3P®) or O-(7-Aza-1-benzotriazolyl)-N,N,N’,N’-tetramethyluronium- hexafluorophosphat (HATU) to provide compounds of formula (III) wherein G is G3 and G4 as described for example in Synthesis 2013, 45, 1569 and J. Prakt. Chem. 1998, 340, 581. Subsequent reaction with an amine of the formula (VI) provides compounds of formula (V). Alternatively, compounds of formula (VI) can be converted to compounds of formula (V) by reaction with an anhydride of formula (III) wherein G is G5 as described for example in WO2010100405.

The compounds of formula (Via), wherein R⁴, R⁵, R⁶, R⁷ and R⁸ are as defined for compounds of formula (I), and R⁹ is halogen, can be obtained by transformation of a compound of formula (VII), wherein R², R³, R⁴, R⁵, R⁶, R⁷ and R⁸ are as defined for compounds of formula (I), and R⁹ is halogen (Scheme 5).

As shown in scheme 5, compounds (VI I) can be converted to compounds (Via) by means of methods known to those skilled in the art and described for example in US6437138, US6127386, Tetrahedron Lett. 2010, 4053. For example, the reaction can be performed in an organic solvent such as THF, DCM or methanol; in the presence of hydrogen gas and a catalyst such as nickel, Raney-Nickel, nickel aluminide or bis(benzonitrile)dichloropalladium [2,2'-Biquinoline]-4,4'-dicarboxylic acid potassium salt (1 :2). Depending on the isolation protocol, compounds (Via) can also be obtained and used in following transformations in their salt form (i.e. hydrochloride salt, hydrobromide salt, trifluoroacetate salt, paratoluensulfonic acid salt, and others known to the person skilled in the art).

The compounds of formula (Vila), wherein R⁴, R⁵, R⁶, and R⁷ are as defined for compounds of formula (I), and R⁹ is halogen, can be obtained by transformation of a compound of formula (VIII), wherein R⁴, R⁵, and R⁶ are as defined for compounds of formula (I), and R⁹ is halogen, with a compound of formula (IX), wherein R⁷ is as defined for compounds of formula (I), and Q is halogen or Q3, as defined in Scheme 2 (Scheme 6).

Scheme 6

As shown in Scheme 6, compounds (VIII) can be converted to compounds (Vila) by methods known to those skilled in the art and described for example in Angew. Chem. Int. Ed. 2016, 5299; J. Am. Chem. Soc. 2018, 5322; WO 2021/153720, WO 2010/150192, WO 2018/013774. For example, the reaction can be performed in inert organic solvent, such as DCM, dioxane or THF, in the presence of a base, such as TEA, pyridine or 1 ,8- diazabicyclo[5.4.0]undec-7-ene. Alternatively, as known to those skilled in the art, compound (VIII) in a salt form (i.e. hydrochloride salt, hydrobromide salt, trifluoroacetate salt, paratoluensulfonic acid salt, and others known to the person skilled in the art) can be similarly used in a conversion to compound (Vila).

The compounds of formula (VIII), wherein R⁴, R⁵, and R⁶ are as defined for compounds of formula (I), and R⁹ is halogen can be obtained by transformation of a compound of formula (X), wherein R⁴, R⁵, and R⁶ are as defined for formula (I), R⁹ is halogen, and R¹⁰ is Ci-Ce-alkyl (Scheme 7).

As shown in Scheme 7, compounds (X) can be converted to compounds (VIII) by methods known to those skilled in the art and described for example in W02002/059117, J. Med. Chem. 2003, 5238, J. Med. Chem. 2003, 46, 1845, Org. Lett. 2022, 2064. For example, the reaction can be performed in organic solvent, such as DCM, dioxane or THF, in the presence of an organic or inorganic acid, such as hydrochloric acid, trifluoroacetic acid or paratoluensulfonic acid. Compounds (VI 11) can also be obtained and used in following transformations in their salt form (i.e. hydrochloride salt, hydrobromide salt, trifluoroacetate salt, paratoluensulfonic acid salt, and others known to the person skilled in the art). The compounds of formula (X), wherein R⁴, R⁵, and R⁶ are as defined for formula (I), R⁹ is halogen, and R¹⁰ is Ci-Ce-alkyl, can be obtained by transformation of a compound (XI) wherein R⁴ is as defined for compounds of formula (I), and R⁹ is halogen, with an alkylating agent of formula (Xlla), wherein R⁵, and R⁶ are as defined for formula (I), R¹⁰ is Ci-Ce-alkyl and Q is halogen, hydroxyl, or Q1 , Q2 or Q3 (Scheme 8).

As shown in Scheme 8, compounds (XI) can be converted by an alkylative reaction with (Xlla) (when Q is i.e. halogen, Q1 or Q2) to compounds (X) by methods known to those skilled in the art and described for example in J. Chem. Inf. Model. 2020, 60, 1028; J. Med. Chem. 2003, 46, 1845; WO 2020/005935. For example, the reaction can be performed in organic solvent, such as DMF, acetone or acetonitrile in the presence of a base, such as cesium carbonate, sodium hydride or sodium carbonate. Alternatively, compounds (XI) can be converted by a Mitsunobu reaction with (Xlla) (when Q is Q3) by methods known to those skilled in the art and described for example in WO 2005/035532; WO 2000/071508; J. Med. Chem. 2020, 63, 14867. For example, the reaction can be performed in organic solvent, such as toluene, THF or DCM in the presence of an azadicarboxylate reagent, such as diethyl azadicarboxylate or diisopropyl azadicarboxylate, and a phospine reagent, such as triphenyl phosphine. Alternatively, compound (XI) can be converted by an alkylative reaction with aziridine (XI I b) to compounds (X) by methods known to those skilled in the art and described for example in WO 2008/109613. For example, the reaction can be performed in organic solvent, such as acetonitrile in the presence of a base, such as potassium carbonate, sodium hydride or sodium carbonate.

The compounds of formula (Via), wherein R⁴, R⁵, R⁶ and R⁷ are as defined for compounds of formula (I), and R⁹ is halogen or cyano, can be obtained by transformation of a compound of formula (XIV), wherein R⁴, R⁵, R⁶ and R⁷ are as defined for formula (I), R⁹ is halogen or cyano, and R¹¹ is halogen, via intermediate of formula (Xllla), wherein R⁴, R⁵, R⁶ and R⁷ are as defined for formula (I), R⁹ is halogen or cyano, and R¹² is Ci-Ce-alkyl. Alternatively, compounds (Via) can be obtained via intermediate of formula (Xlllb), wherein R⁴, R⁵, R⁶ and R⁷ are as defined for formula (I), and R⁹ is halogen or cyano (Scheme 9). Scheme 9

As shown in scheme 9, compounds (XIV) can be converted into intermediates (Xllla), wherein R¹² is Ci-Ce- alkyl or benzyl, by means of a nucleophilic substitution reaction with imidodicarbonate esters as known to those skilled in the art and described for example in WO 2003/051276; WO 2005/082859; Biochem. Pharmacol. 2007, 73, 1558; WO 2010/024430, WO 2016/128529. For example, the reaction can be performed in organic solvent, such as DMF, THF or acetonitrile in the presence of a base, such as cesium carbonate, sodium hydride, potassium carbonate, or sodium carbonate. Next intermediates (Xllla) can be converted into compounds (Via) by means of deprotection reaction under acidic conditions. For example, the reaction can be performed in organic solvent such as dioxane, ethyl acetate (EtOAc), THF, DCM, or acetonitrile in the presence of an organic or inorganic acid, such as hydrochloric acid, trifluoroacetic acid or paratoluensulfonic acid. Compounds (Via) can also be obtained and used in following transformations in their salt form (i.e. hydrochloride salt, hydrobromide salt, trifluoroacetate salt, paratoluensulfonic acid salt, and others known to the person skilled in the art). This is described for example in WO 2016/128465, WO 2005/082859, WO 2010/024430. Alternatively, compounds (XIV) can be converted into intermediates (XI II b) by means of reaction with an azide salt as known to those skilled in the art and described for example in Bioorg. Chem. 2021 , 108, 104654; J. Med. Chem. 2003, 46, 453. For example, the reaction can be performed in organic solvent, such as acetone, DMF, dimethyl sulfoxide (DMSO), THF, dioxane or a mixture with an organic solvent and water in the presence of sodium azide, potassium azide or lithium azide. Next intermediates (XI II b) can be converted into compounds (Via) by means of azide moiety reduction. For example, the reaction can be performed in organic solvent such as ethanol, methanol, THF, EtOAc or mixture of organic solvent and water in the presence of hydrogen gas and a catalyst such as a palladium species, palladium on charcoal or a platinum species. This is for example described in J. Med. Chem. 2003, 46, 453; Tetrahedron 2005, 61, 2217. Alternatively, the reaction can be performed in mixture of water and an organic solvent such as THF, dioxane or toluene in the presence of triphenyl phosphine as described, for example, in WO 2002/036734. The compounds of formula (XIV), wherein R⁴, R⁵, R⁶ and R⁷ are as defined for formula (I), R⁹ is halogen or cyano, and R¹¹ is halogen, can be obtained by transformation of a compound of formula (XV), wherein R⁴, R⁵, R⁶ and R⁷ are as defined for compounds of formula (I), and R⁹ is halogen or cyano (Scheme 10).

Scheme 10

As shown in scheme 10, compounds (XV) can be converted into compounds (XIV) by means of benzylic halogenation reaction as known to those skilled in the art and described for example in Bioorg. Med. Chem. 2008, 16, 3309; CN101407462, Org. Lett. 2020, 22, 4553; WO 2014/207052, CN107501171 . For example, the reaction can be performed in an organic solvent such as carbon tetrachloride, chloroform, acetonitrile, toluene, or chlorobenzene in the presence of a halogenating agent such as N-chloro succinimide, N-bromo succinimide, bromine, chlorine, 1 ,3-dibromo 5,5-dimethylhydantoin or tribromoisocyanuric acid in the optional presence of sub-stoichiometric amount of azobisisobutyronitrile or 1 ,1'-azobis(cyclohexanecarbonitrile).

The compounds of formula (XV), wherein R⁴, R⁵, R⁶ and R⁷ are as defined for compounds of formula (I), and R⁹ is halogen or cyano, can be obtained by transformation of a compound of formula (XVI), wherein R⁴, R⁵, and R⁶ are as defined for compounds of formula (I), and R⁹ is halogen or cyano, with a compound of formula (IX), wherein R⁷ is as defined for formula (I), and Q is halogen or Q3 (Scheme 11).

Scheme 1 1

As shown in Scheme 1 1 , compounds (XVI) can be converted to compounds (XV) by methods known to those skilled in the art and described for example in Angew. Chem. Int. Ed. 2016, 5299; J. Am. Chem. Soc. 2018, 5322; WO 2021/153720, WO 2010/150192, WO 2018/013774, WO 2021/153720. For example, the reaction can be performed in inert organic solvent, such as DCM, dioxane or THF, in the presence of a base, such as TEA, pyridine or 1 ,8-Diazabicyclo[5.4.0]undec-7-ene. Alternatively, as known to those skilled in the art, compound (XVI) in a salt form (i.e. hydrochloride salt, hydrobromide salt, trifluoroacetate salt, paratoluensulfonic acid salt, and others known to the person skilled in the art) can be similarly used in a conversion to compound (XV).

The compounds of formula (XVI), wherein R⁴, R⁵, and R⁶ are as defined for compounds of formula (I), and R⁹ is halogen or cyano, can be obtained by transformation of a compound of formula (XVII), wherein R⁴, R⁵, and R⁶ are as defined for formula (I), R⁹ is halogen or cyano, and R¹⁰ is Ci-Ce-alkyl (Scheme 12). Scheme 12

As shown in Scheme 12, compounds (XVII) can be converted to compounds (XVI) by methods known to those skilled in the art and described for example in WO 2002/059117, J. Med. Chem. 2003, 5238, J. Med. Chem. 2003, 46, 1845, Org. Lett. 2022, 2064, WO 2019/244066. For example, the reaction can be performed in organic solvent, such as DCM, dioxane or THF, in the presence of an organic or inorganic acid, such as hydrochloric acid, trifluoroacetic acid or paratoluensulfonic acid. Compounds (XVI) can also be obtained and used in following transformations in their salt form (i.e. hydrochloride salt, hydrobromide salt, trifluoroacetate salt, paratoluensulfonic acid salt, and others known to the person skilled in the art).

The compounds of formula (XVII), wherein R⁴, R⁵, and R⁶ are as defined for formula (I), R⁹ is halogen or cyano, and R¹⁰ is Ci-Ce-alkyl, can be obtained by transformation of compound (XVIII), wherein R⁴ is as defined for formula (I), and R⁹ is halogen or cyano, with an alkylating agent of formula (Xlla), wherein R⁵ and R⁶ are as defined for formula (I), R¹⁰ is Ci-Ce-alkyl, and Q is halogen, hydroxyl, Q1 , Q2, or Q3 (Scheme 13).

Scheme 13

As shown in Scheme 13, compounds (XVIII) can be converted by an alkylative reaction with (Xlla) (when Q is i.e. halogen, Q1 or Q2) to compounds (XVII) by methods known to those skilled in the art and described for example in J. Chem. Inf. Model. 2020, 60, 1028; J. Med. Chem. 2003, 46, 1845; W02020005935; CN113563238. For example, the reaction can be performed in organic solvent, such as DMF, acetone or acetonitrile in the presence of a base, such as cesium carbonate, sodium hydride or sodium carbonate. Alternatively, compounds (XVIII) can be converted by a Mitsunobu reaction with (Xlla) (when Q is Q3) by methods known to those skilled in the art and described for example in J. Med. Chem. 2016, 59, 5356; WO 2005/035532; WO 2000/071508; J. Med. Chem. 2020, 63, 14867. For example, the reaction can be performed in organic solvent, such as toluene, THF or DCM, in the presence of an azadicarboxylate reagent, such as diethyl azadicarboxylate or diisopropyl azadicarboxylate, and a phospine reagent, such as triphenyl phosphine. Alternatively, compounds (XVIII) can be converted by an alkylative reaction with aziridine (XI lb) to compounds (XVII) by methods known to those skilled in the art and described for example in J. Org. Chem. 2013, 78, 3867; J. Chem. Res. 2008, (5), 297; JP 04208254. For example, the reaction can be performed in organic solvent, such as acetonitrile in the presence of a base, such as potassium carbonate, sodium hydride or sodium carbonate.

The compounds of formula (Va), wherein R¹, R², R³, R⁴, R⁵, R⁶, and R⁷ are as defined for compounds of formula (I), and R⁹ is halogen or cyano, can be obtained by transformation of a compound of formula (XIX), wherein R¹, R², R³, R⁴, R⁵, and R⁶ are as defined for compounds of formula (I), and R⁹ is halogen or cyano, with a compound of formula (VII), wherein R⁷ is as defined for compounds of formula (I), and G is halogen or Q3 (Scheme 14).

Scheme 14

As shown in Scheme 14, compounds (XIX) can be converted to compounds (Va) by methods known to those skilled in the art and described for example in Angew. Chem. Int. Ed. 2016, 5299; J. Am. Chem. Soc. 2018, 5322; WO 2021/153720, WO 2010/150192, WO 2018/013774. For example, the reaction can be performed in inert organic solvent, such as DCM, dioxane or THF, in the presence of a base, such as TEA, pyridine, 1 ,8- Diazabicyclo[5.4.0]undec-7-ene or N-methylimidazole. Alternatively, as known to those skilled in the art, compound (XIX) in a salt form (i.e. hydrochlode salt, hydrobrode salt, trifluoroacetate salt, para-toluensulfonic acid salt, and others known to the person skilled in the art) can be similarly used in a conversion to compound (Va).

The compounds of formula (XIX), wherein R¹, R², R³, R⁴, R⁵, and R⁶ are as defined for compounds of formula (I), and R⁹ is halogen or cyano, can be obtained by transformation of a compound of formula (XX), wherein R¹ , R², R³, R⁴, R⁵, and R⁶ are as defined for compounds of formula (I), R⁹ is halogen or cyano, and R¹⁰ is Ci-Ce- alkyl (Scheme 15).

Scheme 15

As shown in Scheme 15, compounds (XX) can be converted to compounds (XIX) by methods known to those skilled in the art and described for example in WO 2002/059117, J. Med. Chem. 2003, 5238, J. Med. Chem. 2003, 46, 1845, Org. Lett. 2022, 2064, WO 2019/244066. For example, the reaction can be performed in organic solvent, such as DCM, dioxane or THF, in the presence of an organic or inorganic acid, such as hydrochloric acid, trifluoroacetic acid or para-toluensulfonic acid. Compounds (XIX) can also be obtained and used in following transformations in their salt form (i.e. hydrochloride salt, hydrobromide salt, trifluoroacetiate salt, paratoluensulfonic acid salt, and others known to the person skilled in the art).

The compounds of formula (XX), wherein R¹, R², R³, R⁴, R⁵, and R⁶ are as defined for compounds of formula (I), R⁹ is halogen or cyano, and R¹⁰ is Ci-Ce-alkyl, can be obtained by transformation of a compound of formula (XXI), wherein R², R³, R⁴, R⁵, R⁶ are as defined for compounds of formula (I), R⁹ is halogen or cyano, and R¹⁰ is Ci-Ce-alkyl, with an acid chloride or activated acylating agent of formula (III), wherein R¹ is as defined for compounds of formula (I), and G is as described in Scheme 1 (Scheme 16).

Scheme 16

As shown in Scheme 16, compound (Illa), is activated to compounds of formula (III) by methods known to those skilled in the art and described for example in Tetrahedron 2005, 61 (46), 10827-10852. For example, when not commercially available, compounds of formula (III) where G is halogen are formed by treatment of compounds of formula (Illa) with for example, oxalyl chloride or thionyl chloride in the presence of catalytic quantities of DMF in inert solvents such as DCM or THF, at temperatures between 25 and 170°C, preferably between 25 and 80°C. Treatment of (XXI) with compounds of formula (III), optionally in the presence of a base, e.g. TEA or pyridine leads to compounds of formula (XX). Alternatively, compounds of formula (XX) can be prepared by treatment of compounds of formula (Illa) with dicyclohexyl carbodiimide (DCC) or 1 -ethyl-3-(3- dimethylaminopropyl)carbodiimide (EDC) to give the activated species (III), wherein G is G1 or G2, in an inert solvent, e.g. pyridine, or THF, optionally in the presence of a base, e.g. TEA, at temperatures between room temperature and 180°C. In addition, an acid of the formula (Illa) can also be activated by reaction with a coupling reagent such as propanephosphonic acid anhydride (T3P®) or O-(7-Aza-1-benzotriazolyl)-N,N,N’,N’- tetramethyluronium-hexafluorophosphat (HATU) to provide compounds of formula (III) wherein G is G3 and G4 as described for example in Synthesis 2013, 45, 1569 and J. prakt. Chem. 1998, 340, 581 . Subsequent reaction with an amine of the formula (XXI) provides compounds of formula (XX). Alternatively, compounds of formula (XXI) can be converted to compounds of formula (XX) by reaction with an anhydride of formula (III) wherein G is G5 as described for example in WO 2010/100405.

The compounds of formula (XXIa), wherein R⁴, R⁵, and R⁶ are as defined for formula (I), R⁹ is halogen, and R¹⁰ is Ci-Ce-alkyl, can be obtained by transformation of a compound of formula (XXII), wherein R⁴, R⁵, and R⁶ are as defined for compounds of formula (I), R⁹ is halogen, and R¹⁰ is Ci-Ce-alkyl (Scheme 17). Scheme 17

As shown in scheme 17, compounds (XXII) can be converted to compounds (XXIa) by means of methods known to those skilled in the art and described for example in US6437138, US6127386, Tetrahedron Lett. 2010, 4053. For example, the reaction can be performed in an organic solvent such as THF, DCM or methanol; in the presence of hydrogen gas and a catalyst such as nickel, Raney-Nickel, nickel aluminide, or bis(benzonitrile)dichloropalladium [2,2'-biquinoline]-4,4'-dicarboxylic acid potassium salt (1 :2). Depending on the isolation protocol, compounds (XXIa) can also be obtained and used in following transformations in their salt form (i.e. hydrochloride salt, hydrobromide salt, trifluoroacetate salt, paratoluensulfonic acid salt, and others known to the person skilled in the art).

Alternatively, the compounds of formula (XXIa), wherein R⁴, R⁵, and R⁶ are as defined for compounds of formula (I), and R⁹ is halogen or cyano, and R¹⁰ is Ci-Ce-alkyl, can be obtained by transformation of a compound of formula (XXIV), wherein R⁴, R⁵, and R⁶ are as defined for formula (I), R⁹ is halogen or cyano, R¹¹ is halogen, and R¹⁰ is Ci-Ce-alkyl, via intermediate of formula (XXIII), wherein R⁴, R⁵, and R⁶ are as defined for formula (I), R⁹ is halogen or cyano, and R¹⁰ is Ci-Ce-alkyl (Scheme 18).

Scheme 18

As shown in scheme 18, compounds (XXIV) can be converted into intermediates (XXIII) by means of reaction with an azide salt as known to those skilled in the art and described for example in Bioorg. Chem. 2021 , 108, 104654; J. Med. Chem. 2003, 46, 453. For example, the reaction can be performed in organic solvent, such as acetone, DMF, DMSO, THF, dioxane or a mixture with an organic solvent and water in the presence of sodium azide, potassium azide, or lithium azide. Next intermediates (XXIII) can be converted into compounds (XXIa) by means of azide moiety reduction. For example, the reaction can be performed in organic solvent such as ethanol, methanol, THF, EtOAc or mixture of organic solvent and water in the presence of hydrogen gas and a catalyst such as a palladium species, palladium on charcoal or a platinum species. This is for example described in J. Med. Chem. 2003, 46, 453; Tetrahedron 2005, 61, 2217. Alternatively, the reaction can be performed in mixture of water and an organic solvent such as THF, dioxane or toluene in the presence of triphenyl phosphine as described, for example, in WO 2002/036734.

The compounds of formula (XX), wherein R⁴, R⁵, and R⁶ are as defined for compounds of formula (I), R⁹ is halogen or cyano, R¹⁰ is Ci-Ce-alkyl and R¹¹ is halogen can be obtained by transformation of a compound of formula (XVII), wherein R⁴, R⁵ and R⁶ are as defined for compounds of formula (I), R⁹ is halogen or cyano and

R¹⁰ is Ci-C₆-alkyl (Scheme 19).

Scheme 19

As shown in scheme 19, compounds (XVII) can be converted into compounds (XXIV) by means of benzylic halogenation reaction as known to those skilled in the art and described for example in Bioorg. Med. Chem. 2008, 16, 3309; CN101407462, Org. Lett. 2020, 22, 4553; WO 2014/207052, CN107501171 . For example, the reaction can be performed in an organic solvent such as carbon tetrachloride, chloroform, acetonitrile, toluene or chlorobenzene in the presence of a halogenating agent such as N-chloro succinimide, N-bromo succinimide, bromine, chlorine, 1 ,3-dibromo 5,5-dimethylhydantoin or tribromoisocyanuric acid in the optional presence of sub-stoichiometric amount of azobisisobutyronitrile or 1 ,1'-azobis(cyclohexanecarbonitrile).

The compounds of formula (XXIb), wherein R³, R⁴, R⁵, and R⁶ are as defined for compounds of formula (I), and R⁹ is halogen or cyano, and R¹⁰ is Ci-Ce-alkyl can be obtained by transformation of a compound of formula (XXV), wherein R³, R⁴, R⁵, and R⁶ are as defined for formula (I), R⁹ is halogen or cyano and R¹⁰ is Ci-Ce-alkyl (Scheme 20).

Scheme 20

As shown in scheme 20, compounds (XXV) can be converted into compounds (XXIb) by means known to those skilled in the art as reductive aminations and described for example in WO 2018/148626, Bioorg. Med. Chem. Lett. 2003, 13, 1725; J. Org. Chem. 2020, 85, 6626. For example, the reaction can be performed in organic solvent such as methanol, ethanol, acetic acid, DMF, or chloroform, in the presence of ammonia, ammonium acetate, ammonium formate, ammonium chloride, hydroxylamine or hydroxylamine hydrochloride; with an optional base such as TEA, pyridine, sodium acetate or potassium carbonate; followed by the use of a reducing agent such as sodium cyanoborohydride, zinc or a zinc species or hydrogen atmosphere with the aid of an catalytic amount of a metallic species such as palladium on charcoal, Nickel or Cobalt. The transformation can be optionally performed in two individual operations (namely imine or oxime formation and reduction) with the isolation of the transient imine or oxime intermediates. Alternatively, the transformation can be performed by means of a transamination reaction as described for example Org. Process Res. Dev. 2014, 18, 788; Green Chem. 2017, 19, 474. For example, the reaction can be performed in an aqueous buffer with pH range between 4 and 10 in the optional presence of an organic cosolvent such as methanol, ethanol, acetonitrile, isopropanol, THF, DMSO; in the presence of isopropylamine and a catalytic system comprising pyridoxal phosphate and a transaminase enzyme, such as omega transaminases.

The compounds of formula (XXV), wherein R³, R⁴, R⁵, and R⁶ are as defined for compounds of formula (I), R⁹ is halogen or cyano, and R¹⁰ is Ci-Ce-alkyl, can be obtained by transformation of a compound of formula (XXVI), wherein R³ and R⁴ are as defined for compounds of formula (I), and R⁹ is halogen or cyano, with an alkylating agent of formula (Xlla), wherein R⁵ and R⁶ are as defined for formula (I), R¹⁰ is Ci-Ce-alkyl, and Q is halogen, hydroxyl, or Q1 , Q2, or Q3 (Scheme 21).

As shown in Scheme 21 , compounds (XXVI) can be converted by an alkylative reaction with (Xlla) (when Q is i.e. halogen or sulfonate Q1 or Q2) to compounds (XXV) by methods known to those skilled in the art and described for example in J. Chem. Inf. Model. 2020, 60, 1028; J. Med. Chem. 2003, 46, 1845; WO 2020/005935; CN113563238; Helv. Chim. Acta 1989, 72, 1216; ACS Chem. Biol. 2017, 12, 2570, J. Am. Chem. Soc. 2012, 134(4), 2216. For example, the reaction can be performed in organic solvent, such as DMF, acetone or acetonitrile in the presence of a base, such as cesium carbonate, sodium hydride or sodium carbonate. Alternatively, compounds (XXVI) can be converted by a Mitsunobu reaction with (Xlla) (when Q is Q3) by methods known to those skilled in the art and described for example in WO 2005/035532; WO 2000/071508; J. Med. Chem. 2020, 63, 14867; Bioorg. Med. Chem. Lett. 2012, 22, 1633. For example, the reaction can be performed in organic solvent, such as toluene, THF, or DCM in the presence of an azadicarboxylate reagent, such as diethyl azadicarboxylate or diisopropyl azadicarboxylate, and a phospine reagent, such as triphenyl phosphine. Alternatively, compounds (XXVI) can be converted by an alkylative reaction with aziridine (XII b) to compounds (XXV) by methods known to those skilled in the art and described for example in WO 2008/109613. For example, the reaction can be performed in organic solvent, such as acetonitrile in the presence of a base, such as potassium carbonate, sodium hydride or sodium carbonate. The compounds of formula (Va), wherein R¹, R², R³, R⁴, R⁵, R⁶ and R⁷ are as defined for compounds of formula (I), and R⁹ is halogen or cyano, can be obtained by transformation of a compound of formula (XXVII), wherein R¹, R², R³, and R⁴ are as defined for compounds of formula (I), and R⁹ is halogen or cyano, with an alkylating agent of formula (XVI I la) , wherein R⁵, R⁶ and R⁷ are as defined for compounds of formula (I), and Q is halogen, hydroxy, Q1 , Q2, or Q3 (Scheme 22).

Scheme 22

As shown in Scheme 22, compounds (XXVII) can be converted by an alkylative reaction with (XXVIlla) (when Q is i.e. halogen, Q1 or Q2) to compounds (Va) by methods known to those skilled in the art and described for example in Med. Chem. Res. 2015, 24(1 1), 3803, Molecules 2020, 25(22), 5459, Org. Lett. 2021 , 23(13), 5102. For example, the reaction can be performed in organic solvent, such as DMF, acetone or acetonitrile, in the presence of a base, such as cesium carbonate, sodium hydride or sodium carbonate. Alternatively, compounds (XXVII) can be converted by a Mitsunobu reaction with (XXVIlla) (when Q is hydroxy) by methods known to those skilled in the art and described for example in Bioorg. Med. Chem. Lett. 2009, 19(1), 119-122, Eur. J. Med. Chem. 2017, 137, 63-75. For example, the reaction can be performed in organic solvent, such as toluene, THF, or DCM in the presence of an azadicarboxylate reagent, such as diethyl azadicarboxylate or diisopropyl azadicarboxylate, and a phospine reagent, such as triphenyl phosphine. Alternatively, compounds (XXVII) can be converted by an alkylative reaction with aziridine (XXVIlIb) to compounds (Va) by methods known to those skilled in the art and described for example in J. Chem. Res. 2008, (5), 297-300, J. Org. Chem. 2014, 79(11), 5121. For example, the reaction can be performed in organic solvent, such as acetonitrile, THF or EtOAc, in the presence of a base, such as potassium carbonate, sodium hydride, pyridine, TEA, or sodium carbonate.

The compounds of formula (VII), wherein R⁴, R⁵, R⁶ and R⁷ are as defined for compounds of formula (I), and R⁹ is halogen or cyano, can be obtained by transformation of compound (XXIX) wherein R⁴ is as defined for compounds of formula (I), and R⁹ is halogen or cyano, with an alkylating agent of formula (XVI Ila), wherein R⁵, R⁶ and R⁷ are as defined for compounds of formula (I), and Q is halogen, hydroxy, Q1 , Q2, or Q3 (Scheme 23).

As shown in Scheme 23, compound (XXIX) can be converted by an alkylative reaction with (XXVIlla) (when Q is i.e. halogen, Q1 , or Q2) to compounds (VII) by methods known to those skilled in the art and described for example in Med. Chem. Res. 2015, 24(1 1), 3803, Molecules 2020, 25(22), 5459, Org. Lett. 2021 , 23(13), 5102. For example, the reaction can be performed in organic solvent, such as DMF, acetone or acetonitrile in the presence of a base, such as cesium carbonate, sodium hydride or sodium carbonate. Alternatively, compounds (XXIX) can be converted by a Mitsunobu reaction with (XXVIlla) (when Q is Q3) by methods known to those skilled in the art and described for example in Bioorg. Med. Chem. Lett. 2009, 19(1), 119-122, Eur. J. Med. Chem. 2017, 137, 63-75. For example, the reaction can be performed in organic solvent, such as toluene, THF or DCM, in the presence of an azadicarboxylate reagent, such as diethyl azadicarboxylate or diisopropyl azadicarboxylate, and a phospine reagent, such as triphenyl phosphine. Alternatively, compound (XXIX) can be converted by an alkylative reaction with aziridine (XXVIlIb) to compounds (VI I) by methods known to those skilled in the art and described for example in J. Chem. Res. 2008, (5), 297-300, J. Org. Chem. 2014, 79(11), 5121. For example, the reaction can be performed in organic solvent, such as acetonitrile, THF or EtOAc, in the presence of a base, such as potassium carbonate, sodium hydride, pyridine, TEA, or sodium carbonate.

The compounds of formula (XV), wherein R⁴, R⁵, R⁶ and R⁷ are as defined for compounds of formula (I), and R⁹ is halogen or cyano, can be obtained by transformation of compound (XXX) wherein R⁴ is as defined for compounds of formula (I), with an alkylating agent of formula (XXVIlla), wherein R⁵, R⁶ and R⁷ are as defined for compounds of formula (I), and Q is halogen, hydroxy, Q1 or Q2 (Scheme 24).

As shown in Scheme 24, compound (XXX) can be converted by an alkylative reaction with (XXVIlla) (when Q is i.e. halogen, Q1 , or Q2) to compounds (XV) by methods known to those skilled in the art and described for example in Med. Chem. Res. 2015, 24(1 1), 3803, Molecules 2020, 25(22), 5459, Org. Lett. 2021 , 23(13), 5102. For example, the reaction can be performed in organic solvent, such as DMF, acetone or acetonitrile in the presence of a base, such as cesium carbonate, sodium hydride or sodium carbonate. Alternatively, compounds (IX) can be converted by a Mitsunobu reaction with (XXIVa) (when Q is Q3) by methods known to those skilled in the art and described for example in Bioorg. Med. Chem. Lett. 2009, 19(1), 1 19-122, Eur. J. Med. Chem. 2017, 137, 63-75. For example, the reaction can be performed in organic solvent, such as toluene, THF or DCM in the presence of an azadicarboxylate reagent, such as diethyl azadicarboxylate or diisopropyl azadicarboxylate, and a phospine reagent, such as triphenyl phosphine. Alternatively, compound (XXX) can be converted by an alkylative reaction with aziridine (XXVIHb) to compounds (XV) by methods known to those skilled in the art and described for example in J. Chem. Res. 2008, (5), 297-300, J. Org. Chem. 2014, 79(11), 5121. For example, the reaction can be performed in organic solvent, such as acetonitrile, THF or EtOAc, in the presence of a base, such as potassium carbonate, sodium hydride, pyridine, TEA, or sodium carbonate.

The compounds of formula (XXVII), wherein R¹, R², R³, and R⁴ are as defined for compounds of formula (I), and R⁹ is halogen or cyano, can be obtained by transformation of a compound of formula (XXXI), wherein R², R³, and R⁴ are as defined for compounds of formula (I), and R⁹ is halogen or cyano, with an acid chloride or activated acylating agent of formula (III), wherein R¹ is as defined for compounds of formula (I), and G is as described in Scheme 1 (Scheme 25).

Scheme 25

As shown in Scheme 25, compound (Illa), is activated to compounds of formula (III) by methods known to those skilled in the art and described for example in Tetrahedron 2005, 61 (46), 10827-10852. For example, when not commercially available, compounds of formula (III) where G is halogen are formed by treatment of compounds of formula (Illa) with for example, oxalyl chloride or thionyl chloride in the presence of catalytic quantities of DMF in inert solvents such as DCM or THF, at temperatures between 25 and 170°C, preferably between 25 and 80°C. Treatment of (XXXI) with compounds of formula (III), optionally in the presence of a base, e.g. TEA or pyridine leads to compounds of formula (XXVII). Alternatively, compounds of formula (XXXI) can be prepared by treatment of compounds of formula (Illa) with dicyclohexyl carbodiimide (DCC) or 1-ethyl- 3-(3-dimethylaminopropyl)carbodiimide (EDC) to give the activated species (III), wherein G is G1 or G2 (scheme 1), in an inert solvent, e.g. pyridine, or THF, optionally in the presence of a base, e.g. TEA, at temperatures between room temperature and 180°C. In addition, an acid of the formula (Illa) can also be activated by reaction with a coupling reagent such as propanephosphonic acid anhydride (T3P®) or O-(7-Aza- 1-benzotriazolyl)-N,N,N’,N’-tetramethyluronium-hexafluorophosphat (HATU) to provide compounds of formula (III) wherein G is G3 and G4 as described for example in Synthesis 2013, 45, 1569 and J. prakt. Chem. 1998, 340, 581. Subsequent reaction with an amine of the formula (XXXI) provides compounds of formula (XXVII). Alternatively, compounds of formula (XXXI) can be converted to compounds of formula (XXVII) by reaction with an anhydride of formula (III) wherein G is G5 (see Scheme 1) as described for example in WO 2010/100405.

The compounds of formula (XXXla), wherein R³ and R⁴ are as defined for compounds of formula (I), and R⁹ is halogen or cyano, can be obtained by transformation of a compound of formula (XXVI), wherein R³ and R⁴ are as defined for compounds of formula (I), and R⁹ is halogen or cyano (Scheme 26).

Scheme 26

As shown in scheme 26, compounds (XXVI) can be converted into compounds (XXXla) by means known to those skilled in the art as reductive aminations and described for example in WO 2018/148626, Bioorg. Med. Chem. Lett. 2003, 13, 1725; J. Org. Chem. 2020, 85, 6626. For example, the reaction can be performed in organic solvent such as methanol, ethanol, acetic acid, DMF, or chloroform, in the presence of ammonia, ammonium acetate, ammonium formate, ammonium chloride, hydroxylamine or hydroxylamine hydrochloride; with an optional base such as TEA, pyridine, sodium acetate or potassium carbonate; followed by the use of a reducing agent such as sodium cyanoborohydride, Zinc or a Zinc species or hydrogen atmosphere with the aid of an catalytic amount of a metallic species such as palladium on charcoal, Nickel or Cobalt. The transformation can be optionally performed in two individual operations (namely imine or oxime formation and reduction) with the isolation of the transient imine or oxime intermediates. Alternatively, the transformation can be performed by means of a transamination reaction as described for example in Org. Process Res. Dev. 2014, 18, 788; Green Chem. 2017, 19, 474. For example, the reaction can be performed in an aqueous buffer with pH range between 4 and 10 in the optional presence of an organic cosolvent such as methanol, ethanol, acetonitrile, isopropanol, THF, DMSO; in the presence of isopropylamine, and a catalytic system comprising pyridoxal phosphate and a transaminase enzyme, such as omega transaminases.

The compounds of formula (XXXIb), wherein R⁴ is as defined for compounds of formula (I), and R⁹ is halogen, can be obtained by transformation of a compound of formula (XXIX), wherein R⁴ is as defined for compounds of formula (I), and R⁹ is halogen (Scheme 27).

Scheme 27

(xxix (XXXIb) As shown in scheme 27, compounds (XXIX) can be converted to compounds (XXXIb) by means of methods known to those skilled in the art and described for example in US6437138, US6127386, Tetrahedron Lett. 2010, 4053. For example, the reaction can be performed in an organic solvent such as THF, DCM or methanol; in the presence of hydrogen gas and a catalyst, such as nickel, Raney-Nickel, nickel aluminide, or Bis(benzonitrile)dichloropalladium [2,2'-Biquinoline]-4,4'-dicarboxylic acid potassium salt (1 :2). Depending on the isolation protocol, compounds (XXXIb) can also be obtained and used in following transformations in their salt form (i.e. hydrochloride salt, hydrobromide salt, trifluoroacetate salt, paratoluensulfonic acid salt, and others known to the person skilled in the art). Depending on the procedure or the reaction conditions, the reactants can be reacted in the presence of a base. Examples of suitable bases are alkali metal or alkaline earth metal hydroxides, alkali metal or alkaline earth metal hydrides, alkali metal or alkaline earth metal amides, alkali metal or alkaline earth metal alkoxides, alkali metal or alkaline earth metal acetates, alkali metal or alkaline earth metal carbonates, alkali metal or alkaline earth metal dialkylamides or alkali metal or alkaline earth metal alkylsilylamides, alkylamines, alkylenediamines, free or N-alkylated saturated or unsaturated cycloalkylamines, basic heterocycles, ammonium hydroxides and carbocyclic amines. Examples which may be mentioned are sodium hydroxide, sodium hydride, sodium amide, sodium methoxide, sodium acetate, sodium carbonate, potassium tert-butoxide, potassium hydroxide, potassium carbonate, potassium hydride, lithium diisopropylamide, potassium bis(trimethylsilyl)amide, calcium hydride, TEA, diisopropylethylamine, triethylenediamine, cyclohexylamine, N-cyclohexyl-N,N-dimethylamine, N,N-diethylaniline, pyridine, 4-(N,N- dimethylamino)pyridine, quinuclidine, N-methylmorpholine, benzyltrimethylammonium hydroxide and 1 ,8- diazabicyclo[5.4.0]undec-7-ene (DBU).

The reactants can be reacted with each other as such, e.g., without adding a solvent or diluent. In most cases, however, it is advantageous to add an inert solvent or diluent or a mixture of these. If the reaction is conducted in the presence of a base, bases which are employed in excess, such as TEA, pyridine, N-methylmorpholine, or N , N-diethylaniline, may also act as solvents or diluents.

The reactions are advantageously conducted in a temperature range from approximately -80°C to approximately +140°C, preferably from approximately -30°C to approximately +100°C, in many cases in the range between ambient temperature and approximately +80°C.

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

As shown in Scheme 28, compounds (XXVII) can also be prepared from compounds (XXXII) by means of methods known to those skilled in the art and described for example in WO2012112946 or W020071 17607. For example, the reaction can be performed in a suitable organic solvent such as DCM or 1 ,2-dichloroethane in the presence of stoichiometric amounts or excess of a lewis acid such as BBrs,, at a temperature between - 78°C to 100°C, preferably between -40°C and room temperature. Scheme 28

(XXXII) (XXVII)

Alternatively, compounds (XXVII) can also be prepared from compounds (XXXII) in the presence of an excess of aqueous concentrated HBr (for example 47%) at temperatures between 0°C and 150°C such as described in WO2010038081 or W02007084786. Alternatively, compounds (XXVII) can also be prepared from compounds (XXXII) in the presence of a thiol, for example ethanethiol, in the presence of a base, such as NaH, NaOH, or a thiolate salt such as sodium methanethiolate, as described in WO2010038081 . Preferably a suitable polar solvent such as DMF, THF or DMSO is used. Suitable reaction temperatures range from -40°C to 180°C but temperatures between room temperature and 100°C are preferred.

As shown in Scheme 29, compound (Illa), is activated to compounds of formula (III) by methods known to those skilled in the art and described for example in Tetrahedron 2005, 61 (46), 10827-10852. For example, when not commercially available, compounds of formula (III) where G is halogen are formed by treatment of compounds of formula (Illa) with for example, oxalyl chloride or thionyl chloride in the presence of catalytic quantities of DMF in inert solvents such as DCM or THF, at temperatures between 25 and 170°C, preferably between 25 and 80°C. Treatment of (XXXIII) with compounds of formula (III), optionally in the presence of a base, e.g. TEA or pyridine, leads to compounds of formula (XXXII). Alternatively, compounds of formula (XXXI) can be prepared by treatment of compounds of formula (Illa) with dicyclohexyl carbodiimide (DCC) or 1-ethyl- 3-(3-dimethylaminopropyl)carbodiimide (EDC) to give the activated species (III), wherein G is G1 or G2 (see scheme 1), in an inert solvent, e.g. pyridine, or THF optionally in the presence of a base, e.g. TEA, at temperatures between room temperature and 180°C. In addition, an acid of the formula (Illa) can also be activated by reaction with a coupling reagent such as propanephosphonic acid anhydride (T3P®) or O-(7-Aza- 1-benzotriazolyl)-N,N,N’,N’-tetramethyluronium-hexafluorophosphate (HATU) to provide compounds of formula (III) wherein G is G3 and G4 (see scheme 1), as described for example in Synthesis 2013, 45, 1569 and J. prakt. Chem. 1998, 340, 581. Subsequent reaction with an amine of the formula (XXXIII) provides compounds of formula (XXXII). Alternatively, compounds of formula (XXXIII) can be converted to compounds of formula (XXXII) by reaction with an anhydride of formula (III), wherein G is G5 as described for example in WO 2010/100405.

Scheme 30

As shown in scheme 30, compounds (XXXIV) can be converted into compounds (XXXIIIa) by means known to those skilled in the art as reductive aminations and described for example in WO 2018/148626, Bioorg. Med. Chem. Lett. 2003, 13, 1725; J. Org. Chem. 2020, 85, 6626. For example, the reaction can be performed in organic solvent such as methanol, ethanol, acetic acid, DMF, or chloroform, in the presence of ammonia, ammonium acetate, ammonium formate, ammonium chloride, hydroxylamine or hydroxylamine hydrochloride; with an optional base such as TEA, pyridine, sodium acetate or potassium carbonate; followed by the use of a reducing agent such as sodium cyanoborohydride, zinc or a zinc species, or hydrogen atmosphere, with the aid of a catalytic amount of a metallic species, such as palladium on charcoal, nickel or cobalt.

The transformation can be optionally performed in two individual operations (namely imine or oxime formation and reduction) with the isolation of the transient imine or oxime intermediates. Alternatively, the transformation can be performed by means of a transamination reaction as described for example in Org. Process Res. Dev. 2014, 18, 788; Green Chem. 2017, 19, 474. For example, the reaction can be performed in an aqueous buffer with pH range between 4 and 10 in the optional presence of an organic cosolvent such as methanol, ethanol, acetonitrile, isopropanol, THF, DMSO; in the presence of isopropyl amine, and a catalytic system comprising pyridoxal phosphate and a transaminase enzyme, such as omega transaminases.

The compounds of formula (XXXI II b), wherein R⁴is as defined for compounds of formula (I), and R⁹ is halogen, can be obtained by transformation of a compound of formula (XXXV), wherein R⁴ is as defined for compounds of formula (I), and R⁹ is halogen (Scheme 31).

Scheme 31

As shown in Scheme 31 , compounds (XXXV) can be converted to compounds (XXXIIIb) by means known to those skilled in the art and described for example in US6437138, US6127386, Tetrahedron Lett. 2010, 4053. For example, the reaction can be performed in an organic solvent such as THF, DCM or methanol; in the presence of hydrogen gas and a catalyst such as nickel, Raney-Nickel, nickel-aluminide, or Bis(benzonitrile)dichloropalladium [2,2'-Biquinoline]-4,4'-dicarboxylic acid potassium salt (1 :2). Depending on the isolation protocol, compounds (XXXIIIb) can also be obtained and used in following transformations in their salt form (i.e. hydrochloride salt, hydrobromide salt, trifluoroacetate salt, paratoluensulfonic acid salt, and others known to the person skilled in the art). Depending on the procedure or the reaction conditions, the reactants can be reacted in the presence of a base. Examples of suitable bases are alkali metal or alkaline earth metal hydroxides, alkali metal or alkaline earth metal hydrides, alkali metal or alkaline earth metal amides, alkali metal or alkaline earth metal alkoxides, alkali metal or alkaline earth metal acetates, alkali metal or alkaline earth metal carbonates, alkali metal or alkaline earth metal dialkylamides, or alkali metal or alkaline earth metal alkylsilylamides, alkylamines, alkylenediamines, free or N-alkylated saturated or unsaturated cycloalkylamines, basic heterocycles, ammonium hydroxides and carbocyclic amines. Examples which may be mentioned are sodium hydroxide, sodium hydride, sodium amide, sodium methoxide, sodium acetate, sodium carbonate, potassium tert-butoxide, potassium hydroxide, potassium carbonate, potassium hydride, lithium diisopropylamide, potassium bis(trimethylsilyl)amide, calcium hydride, TEA, diisopropylethylamine, triethylenediamine, cyclohexylamine, N-cyclohexyl-N,N-dimethylamine, N,N-diethylaniline, pyridine, 4-(N,N- dimethylamino)pyridine, quinuclidine, N-methylmorpholine, benzyltrimethylammonium hydroxide, and 1 ,8- diazabicyclo[5.4.0]undec-7-ene (DBU).

In certain instances, it may be advantageous to achieve direct transformations between the intermediates described herein. For example, as shown in Scheme 32, compounds (lb) wherein R¹, R⁴, R⁵, R⁶ and R⁷ are as defined for formula (I) may be obtained by transformation compounds (Xlllc) wherein R⁴, R⁵, R⁶ and R⁷ are as defined for formula (I), with an acid of formula (Illa) wherein R¹ is as defined for formula (I).

Scheme 32

As depicted in Scheme 32, compounds of formula (Xlllc) may be reacted with compounds of formula (Illa) to yield compounds (lb) utilizing direct ligation methodologies familiar to those skilled in the art, such as those described in J. Org. Chem. 2009, 2203-2206. The transformation may be carried out in an organic solvent selected from, but not limited to, toluene, THF, or DCM. The reaction may be conducted in the presence of an activating agent, such as trimethyl phosphine or triphenylphosphine, and a catalyst, for example, 2,2'-dipyridyl diselenide (CAS 59957-75-4) or 2,2'-dipyridyl disulfide (CAS 2127-03-9). The reaction may be performed at a temperature ranging from -40°C to about 110°C.

Furthermore, compounds (Ic) wherein R⁴, R⁵, R⁶ and R⁷ are as defined for formula (I) may be obtained by transformation of compounds (XlVa) wherein R⁴, R⁵, R⁶ and R⁷ are as defined for formula (I), and R¹¹ is halogen and R¹³is defined as Ci-C4-alkyl, Ci-C4-haloalkyl, C2-C4-alkynyl, Ci-C4-alkoxy-Ci-C4-alkyl, Cs-Ce-cycloalkyl-Ci- Chalky I, Cs-Ce-cycloalkyl, or phenyl, by reaction with cyanate salt for formula (XXXVI) wherein M is defined as a metal such as Li, Na, K, Cs, or an organic ammonium salt such as tetramethylammonium or tetrabutylammonium and an alcohol of formula (XXXVII) wherein R¹³ is defined as Ci-C4-alkyl, Ci-C4-haloalkyl, C2-C4-alkynyl, Ci-C4-alkoxy-Ci-C4-alkyl, C3-C6-cycloalkyl-Ci-C4-alkyl, Cs-Ce-cycloalkyl, or phenyl. This is illustrated in Scheme 33.

Scheme 33

As shown in Scheme 33, compounds (XlVa) may be reacted with a cyanate salt of formula (XXXVI) to yield a reactive intermediate which may be further reacted with an alcohol of formula (XXXVII) to give compounds of formula (Ic). The reaction may either be carried out step-wise where the cyanate salt of formula (XXXVI) is added first, and after full consumption of the starting material, the alcohol of formula (XXXVII) is added subsequently, or the reaction may be carried out directly in the presence of the alcohol that is present in slight excess or as a cosolvent. Similar transformations are described for example in, US2647916 or DE19535083. This transformation may be carried out in organic solvents including but not limited to DMF, THF, DMSO, or acetonitrile, or mixtures thereof. The reaction may be carried out at temperatures between -40 °C and 180 °C, preferably between -20 °C and 60 °C.

The reactants can be reacted with each other as such, e.g., without adding a solvent or diluent. In most cases, however, it is advantageous to add an inert solvent or diluent or a mixture of these. If the reaction is conducted in the presence of a base, bases which are employed in excess, such as TEA, pyridine, N-methylmorpholine, or N , N-diethylaniline, may also act as solvents or diluents.

The reactions are advantageously conducted in a temperature range from approximately -80°C to approximately +140°C, preferably from approximately -30°C to approximately +100°C, in many cases in the range between ambient temperature and approximately +80°C.

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

Salts of compounds of formula (I) can be prepared in a manner known per se. Thus, for example, acid addition salts of compounds of formula (I) are obtained by treatment with a suitable acid or a suitable ion exchanger reagent and salts with bases are obtained by treatment with a suitable base or with a suitable ion exchanger reagent. Salts of compounds of formula (I) can be converted in the customary manner into the free compounds I, acid addition salts, for example, by treatment with a suitable basic compound or with a suitable ion exchanger reagent and salts with bases, for example, by treatment with a suitable acid or with a suitable ion exchanger reagent.

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

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

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

Diastereomer mixtures or racemate mixtures of compounds of formula (I), in free form or in salt form, which can be obtained depending on which starting materials and procedures have been chosen can be separated in a known manner into the pure diastereomers or racemates based on the physicochemical differences of the components, for example by fractional crystallization, distillation and/or chromatography.

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

Pure diastereomers or enantiomers can be obtained according to the invention not only by separating suitable isomer mixtures, but also by generally known methods of diastereoselective or enantioselective synthesis, for example by conducting the process according to the invention with starting materials of a suitable stereochemistry.

N-oxides can be prepared by reacting a compound of the formula (I) with a suitable oxidizing agent, for example the H2<D2/urea adduct in the presence of an acid anhydride, e.g., trifluoroacetic anhydride. Such oxidations are known from the literature, for example from J. Med. Chem. 1989, 32 (12), 2561-73, or WO 2000/15615.

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

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

The Tables A1 to A6 below illustrate specific compounds of the invention.

The compounds according to the following Tables A1 to A6 may be prepared according to the methods described above. The examples which follow are intended to illustrate the invention and show preferred compounds of formula (I). In any of Tables A1 to A6 below, the presence of one or more possible asymmetric carbon atoms in a compound of formula (I) according to the invention means that the compounds may occur in chiral isomeric forms, e.g., enantiomeric or diastereomeric.

The compounds of formula (I) according to the following Tables A1 to A6 can be prepared according to the methods described herein. The examples which follow are intended to illustrate the invention and show preferred compounds of formula (I), in the form of a compound of formulae (I-A1) and (I-A2).

Table A1 provides 288 compounds of formula (I-A1), wherein R², R³ and R⁶ are hydrogen, R⁵ is methyl, and wherein R¹, R⁴, R⁷, and R⁸ are as defined as in table A1 .

(I-A1)

Table A1 Substituent definitions of R¹, R⁴, R⁷, and R⁸: Table A2: Substituent definitions of R¹, R⁴, and R⁸:

Table A2 provides 192 compounds of formula (I- A2), wherein R², R³ and R⁶ are hydrogen, R⁵ is methyl, R⁷ is CF3, and wherein R¹, R⁴, and R⁸ are as defined as in table A2

Table A-3 provides 32 compounds A-3.001 to A- 3.032 of formula (I-A3) wherein R², R³, R⁵, R⁶ and R⁸ are hydrogen, R⁷ is CF3, and R¹, R⁴ are as defined in table Z.

(I-A3)

Table Z: Substituent definitions of R¹ and R⁴: Table A-4 provides 32 compounds A-4.001 to A-4.032 of formula (I-A3) wherein R² is hydrogen, R⁷ is CF3, R⁸ is hydrogen, R³ is hydrogen, R⁵ and R⁶ are CH3; and R¹, R⁴ are as defined in table Z.

Table A-5 provides 32 compounds A-5.001 to A-5.032 of formula (I-A3) wherein R² is hydrogen, R⁷ is CF3, R⁸ is hydrogen, R³ is hydrogen, R⁵ and R⁶ together with the carbon attached to form a cyclopropyl ring and R¹, R⁴ are as defined in table Z.

Table A-6 provides 32 compounds A-6.001 to A-6.032 of formula (I-A3) wherein R² is hydrogen, R⁷ is CF3, R⁸ is hydrogen, R³ is CH3, R⁵ is methyl, R⁶ is hydrogen, and R¹, R⁴ are as defined in table Z.

The compounds of formula (I) according to the invention are preventively and/or curatively valuable active ingredients in the field of pest control, even at low rates of application, which have a very favorable biocidal spectrum and are well tolerated by warm-blooded species, fish, and plants. The active ingredients according to the invention act against all or individual developmental stages of normally sensitive, but also resistant, animal pests, such as insects or representatives of the order Acarina. The insecticidal or acaricidal activity of the active ingredients according to the invention can manifest itself directly, i. e. in destruction of the pests, which takes place either immediately or only after some time has elapsed, for example during ecdysis, or indirectly, for example in a reduced oviposition and/or hatching rate.

Examples of the above-mentioned animal pests are: from the order Anoplurida, for example, Pthirus pubis, Pthirus spp., and Solenopotes capillatus; from the order Aphelenchida, for example, Bursaphelenchus lignicolus, Bursaphelenchus spp., and Bursaphelenchus xylophilus; from the order Araneae, for example, Agelenopsis spp., Eratigena agrestis, Latrodectus mactans, Latrodectus spp., Loxosceles reclusa, Lycosidae spp., Parastatoda tepidariorum, and Pholcus spp. from the order Ascaridida, for example, Ascaris lumbricoides, Ascaris spp., and Heterakis spp. from the order Astigmata, for example, Chorioptes bovis, Chorioptes spp., Cytodites spp., Laminosioptes spp., Otodectes cynotis, Otodectes spp., and Pterolichus spp.; from the order Bacillales, for example, Pasteuria penetrans; from the order Basommatophora, for example, Biomphalaria spp., and Bulinus spp.; from the order Blattana, for example, Blatta orientalis, Blattella asahinai, Blattella germanica, Mastotermes darwiniensis, Mastotermes spp., Periplaneta americana, Periplaneta australasiae, Periplaneta fuliginosa, Shelfordella lateralis, Supella longipalpa, and Supella spp.; from the order Caenogastropoda, for example, Pomacea canaliculata; from the order Camallanida, for example, Dracunculus medinensis; from the order Chilopoda, for example, Geophilus carpophagus, Geophilus spp., and Scutigera spp.; from the order Coleoptera, for example, Acanthoscelides obtectus, Adelium brevicorne, Adelium spp.., Adoretus spp., Aeolus mellillus, Aeolus spp.., Agelastica alni, Agriotes brevis, Agriotes criddlei, Agriotes fuscicollis, Agriotes lineatus, Agriotes littigiosus, Agriotes mancus, Agriotes obscurus, Agriotes proximus, Agriotes rufipalpis, Agriotes sordidus, Agriotes spp., Agriotes sputator, Agriotes ustulatus, Agrypnus spp.., Agrypnus variabilis, Amphimallon solstitiale, Amphimallon majale, Anisoplia austriaca, Anobium punctatum, Anomala orientalis, Anomala rufocuprea, Anoplophora spp., Anthonomus consors, Anthonomus corvulus, Anthonomus elongatus, Anthonomus elutus, Anthonomus eugenii, Anthonomus grandis, Anthonomus haematopus, Anthonomus lecontei, Anthonomus molochinus, Anthonomus morticinus, Anthonomus musculus, Anthonomus nigrinus, Anthonomus phyllocola, Anthonomus pictus, Anthonomus pomorum, Anthonomus quadrigibbus, Anthonomus rectirostris, Anthonomus rubi, Anthonomus santacruzi, Anthonomus signatus, Anthonomus spp., Anthonomus subfasciatus, Anthonomus tenebrosus, Anthrenus spp., Apogonia spp., Ataneus spretulus, Athous spp.., Atom aria spp., Attagenus spp., Aulacophora femoralis, Bruchidius obtectus, Bruchus spp., Callosobruchus chinensis, Cerotoma arcuata, Cerotoma trifurcata, Ceuthorhynchus assimilis, Ceuthorhynchus spp., Ceutorhynchus napi, Chaetocnema aridula, Chaetocnema minuta, Chaetocnema spp., Chyptohypnus nocturnus bicolor, Chyptohypnus spp.., Cleonus mendicus, Collops spp., Conoderus spp.., Conotrachelus nenupphar, Cosmopolites sordidus, Cosmopolites spp., Costelytra zealandica, Cotinis nitida, Cryptohypnus nocturnus (Eschscholtz), Cryptorhynchus lapathi, Ctenicera aeripennis destructor, Ctenicera destructor, Ctenicera spp.., Curculio spp., Cyclocephala lurida, Cyclocephala spp., Cyclocephela borealis, Dermestes spp., Diabrotica speciosa, Diabrotica spp., Diabrotica virgifera, Dicladispa armigera, Dicladispa spp., Diloboderus abderus, Diloboderus spp., Epilachna spp., Epilachna varivestis, Epilachna vigintioctomaculata, Epitrix spp., Exomala orientalis, Faustinus cubae, Gibbium psylloides, Gonocephalum aequatoriale, Gonocephalum bilineatum, Gonocephalum carpentariae, Gonocephalum contractum, Gonocephalum depress urn, Gonocephalum dorsogranosum, Gonocephalum elderi, Gonocephalum hoffmannseggii, Gonocephalum macleaya, Gonocephalum misellum, Gonocephalum patruele, Gonocephalum pusilium, Gonocephalum reticulatum, Gonocephalum rusticum, Gonocephalum seriatum, Gonocephalum setulosum, Gonocephalum simplex, Gonocephalum spp.., Gonocephalum torridum, Gonocephalum tuberculatum, Gonocephalum walker, Hadromorphus glaucus, Hadromorphus spp.., Heteronychus arator, Hispa spp., Holotrichia spp., Hylamorpha elegans, Hylotrupes bajulus, Hypera brunneipennis, Hypera postica, Hypnoidus abbreviates, Hypnoidus nocturnus, Hypnoidus spp.., Hypolithus bicolor, Hypothenemus hampei, Hypothenemus spp., Lachnosterna consanguinea, Lerna oryzae, Leptinotarsa decemlineata, Leptinotarsa spp., Limonius californicus, Limonius canus, Limonius infuscatus, Limonius pctoralis, Limonius spp., Liogenys fuscus, Liogenys spp.., Liogenys suturalis, Lissorhoptrus oryzophilus, Lissorhoptrus spp., Listronotus maculicollis, Lixus spp., Ludius aeripennis destructor, Ludius aeripennis tinctus, Ludius spp.., Maladera castanea, Maladera matrida, Megascelis calcarifera, Megascelis spp., Melanotus opacaicicollis leconte, Melanotus spp.., Meligethes aeneus, Meligethes spp., Melolontha melolontha, Metamasius hemipterus, Microtheca spp., Migdolus spp., Monochamus alternatus, Monochamus spp., Naupactus xanthographus, Niptus hololeucus, Oryctes rhinoceros, Oryzaephilus surinamensis, Otiorrhynchus sulcatus, Oulema melanopus, Oulema oryzae, Oulema spp., Oxycetonia jucunda, Phaedon cochleariae, Pheletes californicus, Pheletes spp.., Phyllophaga cuyabana, Phyllophaga spp., Phyllotreta cruciferae, Phyllotreta spp., Phyllotreta striolata, Popillia japonica, Premnotrypes spp., Psylliodes chrysocephala, Psylliodes spp., Pterohelaeus alternatus, Pterohelaeus spp.., Ptinus spp., Rhizobius ventralis, Rhizopertha dominica, Rhizotrogus majalis, Scelodonta strigicollis, Selatosomus aeripennis aeripennis, Selatosomus aeripennis destructor, Selatosomus destructor, Selatosomus spp.., Sitophilus spp., Sitophilus zeamais, Somaticus angulatus, Sphenophorus levis, Sphenophorus parvulus, Sphenophorus sp., Sphenophorus spp., Sternechus spp., Sternechus subsignatus, Symphy/etes spp., Tenebrio molitor, Tribolium castaneum, Tribolium spp., Trogoderma spp., Tychius spp., Xylotrechus spp., Zabrus spp., and Zabrus tenebrioides; from the order Collembola, for example, Onychiurus armatus; from the order Cyclophyllidea, for example, Echinococcus granulosus, Echinococcus multilocularis, Hymenolepis nana, Taenia saginata, and Taenia solium; from the order Dermaptera, for example, Forficula auricularia; from the order Dictyoptera, for example, Cryptotermes brevis, Incisitermes minor, Kalotermes flavicollis, Marginitermes hubbardi, and Neotermes spp. from the order Diplopoda, for example, Blaniulus guttulatus; from the order Diptera, for example, Aedes aegypti, Aedes albopictus, Aedes japonicus, Aedes spp., Anopheles funestus, Anopheles gambiae, Anopheles sinensis, Anopheles spp., Atylotus spp., Bactrocera spp., Bibio hortulanus, Braula spp., Calliphora erythrocephala, Calliphora spp., Ceratitis capitata, Ceratitis spp., Chrysomya spp., Chrysops spp., Cochliomyia spp., Contarinia spp., Contarinia tritici, Cordylobia anthropophaga, Culex pipiens, Culex spp., Culex tritaeniorhynchus, Culicoides spp., Cuterebra spp., Dacus oleae, Dacus spp., Delia platura, Delia spp., Dermatobia hominis, Drosophila melanogaster, Drosophila spp., Drosophila suzukii, Eusimulium spp., Fannia spp., Gasterophilus spp., Glossina spp., Haematobia spp., Haematopota spp., Hippobosca spp., Hybomitra spp., Hydrellia griseola, Hydrellia philipina, Hydrellia spp., Hydrotaea spp., Hylemia platura, Hylemya spp., Hypoderma spp., Lipoptena spp., Liriomyza asclepiadis, Liriomyza brassicae, Liriomyza huidobrensis, Liriomyza sativae, Liriomyza spp., Liriomyza trifolii, Lucilia cuprina, Lucilia spp., Lutzomyia spp., Lyctus spp., Mayetiola spp., Melophagus spp., Morellia spp., Musca domestica, Musca spp., Odagmia spp., Oestrus spp., Opomyza florum, Opomyza spp., Orseolia oryzae, Orseolia spp., Oscinella frit, Oscinella spp., Pegomyia hyoscyami, Pegomyia spp., Philipomyia spp., Phlebotomus spp., Phorbia spp., Rhinoestrus spp., Sarcophaga spp., Sciara coprophila, Simulium spp., Sitodiplosis spp., Stomoxys spp., Tabanus spp., Tipula oleracea, Tipula paludosa, Tipula spp., Trichosia spp., Wilhelmia spp., and Wohlfahrtia spp.; from the order Dorylaimida, for example, Longidorus breviannulatus, Longidorus elongatus, Longidorus spp., Trichodorus primitivus, Trichodorus spp., and Xiphinema spp.; from the order Echinostomida, for example, Faciola spp.; from the order Hemiptera, for example, Acrosternum hilare, Acrosternum spp., Acyrthosiphon spp., Aeneolamia spp., Agonoscena spp., Aleurodes brassicae, Aleurodes spp., Aleurolobus barodensis, Aleurothrixus spp., Amrasca biguttula, Amrasca spp., Anasa tristis, Antestiopsis orbitalus, Antestiopsis spp., Anuraphis cardui, Aonidiella aurantii, Aonidiella spp., Aphanostigma piri, Aphis citri, Aphis fabae, Aphis glycines, Aphis gossypii, Aphis nasturtii, Aphis pomi, Aphis spiraecola, Aphis spp., Arboridia apicalis, Aspidiella spp., Aspidiotus hederae, Aspidiotus spp., Atanus spp., Aulacorthum solani, Austroasca viridigrisea, Bemisia argentifolii, Bemisia spp., Bemisia tabaci, Blissus insularis, Blissus insularis barber, Blissus Leucopterus, Blissus leucopterus hirtus, Blissus spp., Brachycaudus helichrysii, Brachycolus spp., Brevicoryne brassicae, Brevicoryne spp., Cacopsylla pyri, Cacopsylla pyricola, Cacopsylla spp., Calligypona marginata, Calocoris spp., Campylomma livida, Carneocephala fulgida, Cavelerius spp., Ceratovacuna lanigera, Ceroplastes spp., Chaetosiphon fragaefolii, Chionaspis tegalensis, Chlorita onukii, Chromaphis juglandicola, Chrysomphalus ficus/aonidum , Cicadulina mbila, Cimex hemipterus, Cimex lectularius, Cimex spp., Coccomytilus halli, Coccus spp., Creontiades biseratense, Creontiades dilutus, Creontiades spp., Cryptomyzus ribis, Dalbulus maidis, Dalbulus spp., Dasynus piperis, Dialeurodes spp., Diaphorina citri, Diaphorina spp., Diaspis spp., Diceraeus furcatus, Diceraeus melacanthus, Diceraeus spp., Dichelops furcatus, Dichelops melacanthus, Dichelops spp., Diconocoris hewetti, Distantiella theobroma, Diuraphis spp., Drosicha spp., Dysaphis plantaginea, Dysaphis spp., Dysdercus cingulatus, Dysdercus intermedius, Dysdercus spp., Dysmicoccus spp., Edessa meditabunda, Edessa spp., Empoasca fabae, Empoasca solaria, Empoasca spp., Empoasca vitis, Eriosoma lanigerum, Eriosoma spp., Erythroneura Elegantula, Erythroneura spp., Euchistus spp., Eurygaster integriceps, Eurygaster intergriceps, Eurygaster maura, Eurygaster spp., Euscelis bilobatus, Euschistus heros, Euschistus servus, Euschistus spp., Geococcus coffeae, Geocoris spp., Halyomorpha halys, Halyomorpha spp., Helopeltis spp., Homalodisca coagulata/vitripennis, Horcias nobilellus, Hyalopterus arundinis, Icerya spp., Idiocerus spp., Idioscopus spp., Irbisia pacifica, Irbisia sp., Labops hesperius, Labops sp., Laodelphax spp., Laodelphax striatellus, Lepidosaphes spp., Leptocorisa chinensis, Leptocorisa spp., Leptocorsia acuta, Leptocorsia oratorius, Leptodelphax maculigera, Leptodictya tabida, Leptoglossus phyllopus, Leptoglossus spp., Lipaphis erysimi, Lyctus bruneus, Lygus hesperus, Lygus lineolaris, Lygus spp., Macropes excavatus, Macrosiphum avenae, Macrosiphum euphorbiae, Macrosiphum spp., Mahanarva fimbriolata, Mahanarva spp., Melanaphis sacchari, Metcalfa pruinosa, Metcalfiella spp., Metopolophium dirhodum, Metopolophium spp., Monellia costalis, Monelliopsis pecanis, Murgantia spp., Myzus persicae, Myzus spp., Nasonovia ribisnigri, Neomegalotomus spp., Nephotettix cincticeps, Nephotettix malayanus, Nephotettix nigropictus, Nephotettix parvus, Nephottetix spp., Nephottetix virescens, Neurocolpus nubilus, Nezara antennata, Nezara hilare, Nezara spp., Nezara viridula, Nilaparvata lugens, Nilaparvata spp., Oebalus mexicana, Oebalus poecilus, Oebalus pugnase, Oebalus pugnax, Oebalus spp., Oncometopia spp., Orthezia praelonga, Orthezia spp., Parabemisia myricae, Paracoccus marginatus, Paratrioza cockerelli, Paratrioza spp., Parlatoria pergandei, Parlatoria spp., Pemphigus spp., Peregrinus maidis, Phenacoccus spp., Phloeomyzus passerinii, Phorodon humuli, Phylloxera spp., Phylloxera vastatrix, Piezodorus guildinii, Piezodorus spp., Pinnaspis aspidistrae, Pianococcus citri, Pianococcus spp., Plautia crossota, Protopulvinaria pyriformis, Psallus seriatus, Pseudacysta persea, Pseudatomoscelis seriatus, Pseudaulacaspis pentagona, Pseudococcus comstocki, Pseudococcus spp., Psylla pyri, Psylla pyricola, Psylla spp., Pyrilla spp., Quadraspidiotus perniciosus, Quadraspidiotus spp., Quesada gigas, Rastrococcus spp., Rhodnius prolixus, Rhodnius spp., Rhopalosiphum graminum, Rhopalosiphum padi, Rhopalosiphum pseudobrassicas, Rhopalosiphum spp., Rhopalus maculatus, Riptortus clavatus, Sahlbergella singularis, Saissetia oleae, Saissetia spp., Scaphoideus spp., Scaphoideus titanus, Scaptocoris castanea, Scaptocoris spp., Schizaphis graminum, Schizaphis spp., Scotinophara coarctata, Scotinophara lurida, Scotinophara spp., Scotinophora spp., Selenaspidus articulatus, Selenaspidus spp., Sitobion avenae, Sitobion spp., Sogatella furcifera, Sogatella spp., Sogatodes spp., Spissistilus festinus, Spissistilus spp., Stictocephala festina, Thyanta spp., Tibraca spp., Tinocallis caryaefoliae, Tomaspis spp., Toxoptera spp., Trialeurodes spp., Trialeurodes vaporariorum , Triatoma spp., Trioza spp., Typhlocyba spp., Unaspis spp., Unaspis yanonensis, and Viteus vitifolii; from the order Heteroptera, for example, Piesma quadrata; from the order Hygrophila, for example, Galba spp., and Lymnaea spp. from the order Hymenoptera, for example, Acromyrmex heyri, Acromyrmex lundii, Acromyrmex spp., Athalia rosae, Athalia spp., Atta bisphaerica, Atta capiguara, Atta laevigata, Atta sexdens rubropilosa, Atta spp., Brachymyrmex sp, Camponotus floridanus, Camponotus pennsylvanicus, Camponotus spp., Cephus spp., Crematogaster spp., Diprion spp., Hoplocampa spp., Lasius neglectus, Lasius Neoniger, Lasius niger, Lasius spp., Linepithema humile, Messor structor, Monomorium minimum, Monomorium pharaonis, Myrmica rubra, Paratrechina spp., Pheidole megacephala, Pteromalus spp., Solenopsis geminata, Solenopsis invicta, Solenopsis molesta, Tapinoma melanocephalum, Tapinoma sessile, Technomyrmex albipes, Tetramorium caespitum, and Vespa spp. from the order Isopoda, for example, Armadillidium vulgare, Oniscus asellus, and Porcellio scaber; from the order Isoptera, for example, Caenorhabditis elegans, Coptotermes acinaciformis, Coptotermes curvignathus, Coptotermes formosanus, Cornitermes cumulans, Cornitermes spp.., Globitermes sulphureus, Heterotermes aureus, Heterotermes longiceps, Heterotermes spp.., Heterotermes tenuis, Macrotermes bellicosus, Macrotermes spp., Microtermes, Nasutitermes exitiosus, Nasutitermes walkeri, Neocapritermes opacus, Neocapritermes parvus, Odontotermes obesus, Odontotermes spp., Procornitermes spp., Procornitermes triacifer, Reticulitermes flavipes, Reticulitermes hageni, Reticulitermes hesperus, Reticulitermes lucifugus, Reticulitermes santonensis, Reticulitermes speratu, Reticulitermes speratus, Reticulitermes spp., Reticulitermes verginicus, Reticulitermes virginicus, Schedorhinotermes spp., and Termes obesus; from the order Ixodida, for example, Amblyomma americanum, Amblyomma cajennense, Amblyomma hebraeum, Amblyomma maculatum, Amblyomma spp., Amblyomma variegatum, Argas persicus, Argas reflexus, Argas spp., Dermacentor albipictus, Dermacentor andersoni, Dermacentor marginatus, Dermacentor pictus, Dermacentor reticulatus, Dermacentor spp., Dermacentor variabilis, Haemaphysalis cinnabarina, Haemaphysalis concinna, Haemaphysalis leachi, Haemaphysalis longicorni, Haemaphysalis otophila, Haemaphysalis punctata, Haemophysalis spp., Hyalomma aegypticum, Hyalomma anatolicum, Hyalomma marginatum, Hyalomma mauritanicum, Hyalomma spp., Hyalomma transiens, Ixodes canisuga, Ixodes hexagonus, Ixodes holocyclus, Ixodes pacificus, Ixodes pilosus, Ixodes ricinus, Ixodes rubicundus, Ixodes scapularis, Ixodes spp., Ornithodoros spp., Ornithodorus moubata, Ornithodorus spp., Otobius megnini, Otobius spp., Rhiphicephalus (former Boophilus) microplus, Rhiphicephalus (former Boophilus) spp., Rhipicephalus annulatus, Rhipicephalus appendiculatus, Rhipicephalus bursa, Rhipicephalus calceratus, Rhipicephalus capensis, Rhipicephalus decoloratus, Rhipicephalus evertsi, Rhipicephalus microplus, Rhipicephalus sanguineus, Rhipicephalus spp., Rhipicephalus turanicus, and Rhipicephalus zambeziensis; from the order Julida, for example, Julus hesperus, and Julus spp..; from the order Lepidoptera, for example, Adoxophyes orana, Adoxophyes spp., Agrotis fucosa, Agrotis ipsilon, Agrotis spp., Alabama argillacea, Amyelois transitella, Anarsia lineatella, Anomis flava, Anticarsia gemmatalis, Anticarsia spp., Apamea spp., Bucculatrix thurberiella, Bupalus piniarius, Busseola fusca, Capua reticulana, Carpocapsa pomonella, Cheimatobia brumata, Chilo auricilius, Chilo indicus, Chilo partellus, Chilo polychrysus, Chilo spp., Chilo suppressalis, Chlosyne lacinia, Choristoneura fumiferana, Choristoneura rosaceana, Chrysodeixis includens, Chrysodeixis spp., Cnaphalocrocis medinalis, Cnaphalocrocis spp., Colias eurytheme, Conopomorpha cramarella, Crambus praefectellus, Crambus sp., Crambus spp., Cydia molesta, Cydia pomonella, Cydia spp., Diaphania spp., Diatraea saccharalis, Diatraea spp., Earias insulana, Earias spp., Elasmopalpus lignosellus, Elasmopalpus spp., Ephestia cautella, Ephestia kuehniella, Epinotia spp., Etiella zinckinella, Eupoecilia ambiguella, Eupoecilia spp., Euproctis chrysorrhoea, Euxoa auxiliaris, Euxoa messoria, Euxoa spp., Feltia spp., Fissicrambus mutabilis, Galleria mellonella, Grapholita molesta, Grapholita spp., Helicoverpa armigera, Helicoverpa spp., Helicoverpa zea, Heliothis armigera, Heliothis spp., Heliothis virescens, Heliothis zea, Herpetogramma phaeopteralis, Hofmannophila pseudospretella, Homoeosoma electellum, Homoeosoma nebulella, Homoeosoma spp., Homona magnanima, Keiferia spp., Laphygma spp., Leucinodes spp., Leucoptera coffeella, Leucoptera spp., Lithophane antennata, Lobesia botrana, Lobesia spp., Loxagrotis albicosta, Lymantria dispar, Lymantria spp., Lyonetia clerkella, Malacosoma neustria, Mamestra brassicae, Mamestra spp., Marasmia spp., Maruca spp., Mods latipes, Mods repanda, Mythimna separata, Neoleucinodes spp., Nymphula depundalis, Omiodes indicatus, Oria spp., Ostrinia nubilalis, Ostrinia spp., Panolis flammea, Parapediasia teterrellus, Pectinophora gossypiella, Pectinophora spp., Pediasia triseda, Peridroma saucia, Perileucoptera coffeella, Perileucoptera spp., Phthorimaea operculella, Phthorimaea spp., Phyllocnistis citrella, Phyllocnistis spp., Pieris brassicae, Pieris rapae, Pieris spp., Plusia spp., Plutella maculipennis, Plutella spp., Plutella xylostella, Prays citri, Prodenia spp., Pseudaletia spp., Pseudoplusia includens, Pseudoplusia spp., Rachiplusia nu, Rachiplusia spp., Scirpophaga incertulas, Scirpophaga innotata, Scirpophaga spp., Scripophaga innotata, Scripophaga spp., Sesamia cretica, Sesamia inferens, Sesamia spp., Spodoptera cosmiodes, Spodoptera eridania, Spodoptera exigua, Spodoptera frugiperda, Spodoptera littoralis, Spodoptera litura, Spodoptera spp., Sylepta derogata, Telchin licus, Thermesia gemmatalis, Tinea pellionella, Tineola bisselliella, Tortrix spp., Tortrix viridana, Trichoplusia ni, Trichoplusia spp., Tuta absoluta, and Tuta spp. from the order Littorinimorpha, for example, Oncomelania spp. from the order Lygaeidae, for example, Oxycarenus hyalinipennis; from the order Mesostigmata, for example, Amblyseius fallacis, Dermanyssus gallinae, Dermanyssus spp., Ornithonyssus bursa, Ornithonyssus spp., Ornithonyssus sylviarum, Phytoseiulus, Pneumonyssoides caninum, Raillietia spp., Sternostoma spp., Typhlodromus occidentalis, Varroa jacobsoni, and Varroa spp.; from the order Opisthorchiida, for example, Clonorchis spp., and Opisthorchis spp.; from the order Orthoptera, for example, Acheta domesticus, Gryllotalpa Africana, Gryllotalpa spp., Locusta migratoria, Locusta spp., Melanoplus spp., Scapteriscus berellii, Scapteriscus vicinus, and Schistocerca gregaria; from the order Oxyurida, for example, Enterobius vermicularis; from the order Phthiraptera, for example, Bovicola bovis, Bovicola caprae, Bovicola limbata, Bovicola ovis, Bovicola spp., Damalinia spp., Felicola spp., Felicola subrostratus, Haematopinus asini macrocephalus, Haematopinus eurysternus, Haematopinus spp., Haematopinus suis, Lepikentron ovis, Lepikentron spp., Linognathus oviformis, Linognathus ovillus, Linognathus pedalis, Linognathus setosus, Linognathus spp., Linognathus stenopsis, Linognathus vituli, Pediculus capitis, Pediculus humanus, Pediculus spp., Solenopotes spp., Trichodectes canis, Trichodectes spp., Trimenopon spp., Trinoton spp., Werneckiella equi, and Werneckiella spp. from the order Plagiorchiida, for example, Dicrocoelium spp., and Paragonimus spp. from the order Prostigmata, for example, Aceria sheldoni, Aculus schlechtendali, Aculus spp., Eriophyes cynodoniensis, Halotydeus destructor, and Hemitarsonemus spp.; from the order Pseudophyllidea, for example, Diphyllobothrium latum; from the order Pulmonata, for example, Arion spp., Deroceras reticulatum, Deroceras spp., and Succinea spp.; from the order Rhabditida, for example, Bunostomum spp., Oesophagostomum spp., Ostertagia spp., Strongyloides fuelleborni, Strongyloides spp., Strongyloides stercoralis, and Trichostrongylus spp.; from the order Rodentia, for example, Mus musculus, Rattus norwegicus, and Rattus rattus; from the order Sarcoptiformes, for example, Acarus siro, Acarus spp., Caloglyphus spp., Dermatophagoides farinae, Dermatophagoides peteronyssinus, Knemidocoptes spp., Listrophorus spp., Notoedres cati, Notoedres spp., Psoroptes cuniculi, Psoroptes equi, Psoroptes ovis, Psoroptes spp., Rhizoglyphus spp., Sarcoptes bovis, Sarcoptes canis, Sarcoptes caprae, Sarcoptes equi, Sarcoptes ovis, Sarcoptes rupicaprae, Sarcoptes scabiei, Sarcoptes spp., Sarcoptes suis, and Tyrophagus spp.; from the order Scorpiones, for example, Centruroides sculpturatus, Centruroides vittatus, Hadrurus arizonensis, and Scorpio maurus; from the order Siphonaptera, for example, Ceratophyllus spp., Ctenocephalides canis, Ctenocephalides felis, Echidnophaga gallinacea, Pulex irritans, and Xenopsylla cheopis; from the order Spirurida, for example, Brugia malayi, Brugia timori, Loa loa, Onchocerca volvulus, and Wuchereria; from the order Strongylida, for example, Ancylostoma braziliense, Ancylostoma ceylanicum, Ancylostoma duodenale, Ancylostoma spp., Cooperia spp., Dictyocaulus filaria, Haemonchus contortus, Haemonchus spp., Hyostrongulus spp., and Nematodirus spp.; from the order Symphyla, for example, Scutigerella immaculata; from the order Thysanoptera, for example, Baliothrips biformis, Calliothrips phaseoli, Calliothrips spp., Enneothrips flavens, Enneothrips spp., Frankliniella accidentalis, Frankliniella fusca, Frankliniella occidental, Frankliniella occidentalis , Frankliniella schultzei, Frankliniella spp., Heliothrips spp., Hercinothrips femoralis, Kakothrips spp., Megalurothrips spp., Pezothrips kellyanus, Rhipiphorothrips cruentatus, Scirtothrips citri, Scirtothrips dorsalis, Scirtothrips spp., Stenchaetothrips biformis, Taeniothrips cardamoni, Thrips palmi, Thrips parvispinus, Thrips spp., and Thrips tabaci; from the order Thysanura, for example, Lepisma saccharifera, Lepisma saccharina, Lepisma semicylindrica, and Lepisma vulgaris; from the order Trematoda, for example, Schistosoma spp.; from the order Trichocephalida, for example, Trichinella britovi, Trichinella nativa, Trichinella nelsoni, Trichinella pseudopsiralis, and Trichinella spiralis from the order Trichurida, for example, Trichuris trichuria; from the order Triplonchida, for example, Paratrichodorus spp.; from the order Trombidiformes, for example, Acarapis spp., Acarapis woodi, Aculops pelekassi, Aculops spp., Brevipalpus spp., Bryobia praetiosa, Bryobia rubrioculus, Cheyletiella blakei, Cheyletiella spp., Cheyletiella yasguri, Demodex bovis, Demodex caballi, Demodex canis, Demodex caprae, Demodex equi, Demodex ovis, Demodex spp., Demodex suis, Eotetranychus spp., Eotetranychus willamettei, Epitrimerus pyri, Eriophyes ribis, Eriophyes spp., Eutetranychus spp., Myobia spp., Neoschongastia xerothermobia, Neotrombicula autumnalis, Neotrombicula desaleri, Oligonychus coffeae, Oligonychus ilicis, Oligonychus spp., Ornithocheyletia spp., Panonychus citri, Panonychus spp., Panonychus ulmi, Phyllocoptruta oleivora, Phyllocoptruta spp., Polyphagotarsonemus latus, Polyphagotarsonemus spp., Psorergates ovis, Psorergates spp., Steneotarsonemus spinki, Steneotarsonemus spp., Tarsonemus spp., Tetranychus cinnabarinus, Tetranychus spp., Tetranychus urticae, Trombicula akamushi, Trombicula spp., Vasates lycopersici, and Zetzellia mali; from the order Tylenchida, for example, Anguina agrostis, Anguina pacificae, Anguina spp., Aphelenchoides besseyi, Aphelenchoides spp., Belonolaimus longicaudatus, Belonolaimus spp., Criconema spp., Criconemella spp., Criconemella sp, Criconemoides onoensis, Criconemoides spp., Ditylenchus angustus, Ditylenchus destructor, Ditylenchus dipsaci, Ditylenchus spp., Dolichodorus spp., Globodera rostochiensis, Globodera spp., Helicotylenchus multicinctus, Helicotylenchus spp., Hemicriconemoides spp., Hemicycliophora spp., Heterodera avenae, Heterodera glycines, Heterodera leuceilyma, Heterodera schachtii, Heterodera spp., Heterodera trifolii, Hirschmanniella spp., Hoplolaimus columbus, Hoplolaimus galeatus, Hoplolaimus spp., Macropostonia sp, Meloidogyne arenaria, Meloidogyne graminis, Meloidogyne hapla, Meloidogyne incognita, Meloidogyne javanica, Meloidogyne marylandi, Meloidogyne spp., Meloidogyne sp, Mesocriconema spp., Nacobbus spp., Pratylenchus agilis, Pratylenchus alleni, Pratylenchus brachyurus, Pratylenchus curvitatus, Pratylenchus goodeyi, Pratylenchus neglectans, Pratylenchus neglectus thornei, Pratylenchus penetrans, Pratylenchus sefaensis, Pratylenchus spp., Punctodera spp., Quinisulcius spp., Radopholus similis, Radopholus spp., Rotylenchulus brachyurus, Rotylenchulus reniformis, Rotylenchulus robustus, Rotylenchulus spp., Rotylenchus reniformis, Rotylenchus spp., Scutellonema spp., Subanguina spp., Tylenchorhynchus Claytoni, Tylenchorhynchus dubius, Tylenchorhynchus spp., Tylenchulus semipenetrans, and Tylenchulus spp. from the order Veneroida, for example, Dreissena spp.;

The active ingredients according to the invention can be used for controlling, i. e. containing or destroying, pests of the abovementioned type which occur in particular on plants, especially on useful plants and ornamentals in agriculture, in horticulture and in forests, or on organs, such as fruits, flowers, foliage, stalks, tubers or roots, of such plants, and in some cases even plant organs which are formed at a later point in time remain protected against these pests. Suitable target crops are, in particular, cereals, such as wheat, barley, rye, oats, rice, maize or sorghum; beet, such as sugar or fodder beet; fruit, for example pomaceous fruit, stone fruit or soft fruit, such as apples, pears, plums, peaches, almonds, cherries or berries, for example strawberries, raspberries or blackberries; leguminous crops, such as beans, lentils, peas or soya; oil crops, such as oilseed rape, mustard, poppies, olives, sunflowers, coconut, castor, cocoa or ground nuts; cucurbits, such as pumpkins, cucumbers or melons; fibre plants, such as cotton, flax, hemp or jute; citrus fruit, such as oranges, lemons, grapefruit or tangerines; vegetables, such as spinach, lettuce, asparagus, cabbages, carrots, onions, tomatoes, potatoes or bell peppers; Lauraceae, such as avocado, Cinnamonium or camphor; and also tobacco, nuts, coffee, eggplants, sugarcane, tea, pepper, grapevines, hops, the plantain family and latex plants.

In a particular embodiment, a compound of the formula (I) can control mites, rust mites and spider mites in crops, tress, and plants selected from vegetables (especially tomatoes and cucurbits), citrus, pome fruits, stone fruit, tree nuts, cotton, tropical crops, avocados, ornamentals, beans, soybean, strawberry, and grapes.

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

For example the invention may be used on any of the following ornamental species: Ageratum spp., Alonsoa spp., Anemone spp., Anisodontea capsenisis, Anthemis spp., Antirrhinum spp., Aster spp., Begonia spp. (e.g., B. elatior, B. semperflorens, B. tubereux), Bougainvillea spp., Brachycome spp., Brassica spp. (ornamental), Calceolaria spp., Capsicum annuum, Catharanthus roseus, Canna spp., Centaurea spp., Chrysanthemum spp., Cineraria spp. (C. maritime), Coreopsis spp., Crassula coccinea, Cuphea ignea, Dahlia spp., Delphinium spp., Dicentra spectabilis, Dorotheantus spp., Eustoma grandiflorum, Forsythia spp., Fuchsia spp., Geranium gnaphalium, Gerbera spp., Gomphrena globosa, Heliotropium spp., Helianthus spp., Hibiscus spp., Hortensia spp., Hydrangea spp., Hypoestes phyllostachya, Impatiens spp. (/. Walleriana), Iresines spp., Kalanchoe spp., Lantana camara, Lavatera trimestris, Leonotis leonurus, Lilium spp., Mesembryanthemum spp., Mimulus spp., Monarda spp., Nemesia spp., Tagetes spp., Dianthus spp. (carnation), Canna spp., Oxalis spp., Bellis spp., Pelargonium spp. (P. peltatum, P. Zonale), Viola spp. (pansy), Petunia spp., Phlox spp., Plecthranthus spp., Poinsettia spp., Parthenocissus spp. (P. quinquefolia, P. tricuspidata), Primula spp., Ranunculus spp., Rhododendron spp., Rosa spp. (rose), Rudbeckia spp., Saintpaulia spp., Salvia spp., Scaevola aemola, Schizanthus wisetonensis, Sedum spp., Solanum spp., Surfinia spp., Tagetes spp., Nicotinia spp., Verbena spp., Zinnia spp. and other bedding plants.

For example the invention may be used on any of the following vegetable species: Allium spp. (A sativum, A. cepa, A. oschaninii, A. Porrum, A. ascalonicum, A. fistuiosum), Anthriscus cerefolium, Apium graveolus, Asparagus officinalis, Beta vulgarus, Brassica spp. (B. Oleracea, B. Pekinensis, B. rapa), Capsicum annuum, Cicer arietinum, Cichorium endivia, Cichorum spp. (C. intybus, C. endivia), Citrillus lanatus, Cucumis spp. (C. sativus, C. melo), Cucurbita spp. (C. pepo, C. maxima), Cyanara spp. (C. scolymus, C. cardunculus), Daucus carota, Foeniculum vulgare, Hypericum spp., Lactuca sativa, Lycopersicon spp. (L esculentum, L. lycopersicum), Mentha spp., Ocimum basilicum, Petroselinum crispum, Phaseolus spp. (P. vulgaris, P. coccineus), Pisum sativum, Raphanus sativus, Rheum rhaponticum, Rosemarinus spp., Salvia spp., Scorzonera hispanica, Solanum melongena, Spinacea oleracea, Valerianella spp. (IZ. locusta, V. eriocarpa) and Vicia faba.

Preferred ornamental species include African violet, Begonia, Dahlia, Gerbera, Hydrangea, Verbena, Rosa, Kalanchoe, Poinsettia, Aster, Centaurea, Coreopsis, Delphinium, Monarda, Phlox, Rudbeckia, Sedum, Petunia, Viola, Impatiens, Geranium, Chrysanthemum, Ranunculus, Fuchsia, Salvia, Hortensia, rosemary, sage, St. Johnswort, mint, sweet pepper, tomato and cucumber.

The compounds of formula (I) may be particularly suitable for control of mites, spider mites and rust mites, for example, Acarapis spp.; Acarapis woodi; Acarus siro;Acarus spp.;Aceria sheldoni; Aculops pelekassi; Aculops spp.; Aculus schlechtendali; Aculus spp.; Amblyseius fallacis; Brevipalpus spp.; Brevipalpus phoenicis; Bryobia praetiosa; Bryobia rubrioculus; Caloglyphus spp.; Cheyletiella blakei; Cheyletiella spp.; Cheyletiella yasguri; Chorioptes bovis; Chorioptes spp.; Cytodites spp.; Demodex bovis; Demodex caballi; Demodex canis; Demodex caprae; Demodex equi; Demodex ovis; Demodex spp.; Demodex suis; Dermanyssus gallinae; Dermanyssus spp.; Eotetranychus spp.; Eotetranychus willamettei; Epitrimerus pyri; Eriophyes ribis; Eriophyes spp.; Eriophyes vitis; Eutetranychus spp.; Halotydeus destructor; Hemitarsonemus spp.; Knemidocoptes spp.; Laminosioptes spp.; Listrophorus spp.; Myobia spp.; Neoschongastia xerothermobia; Neotrombicula autumnalis; Neotrombicula desaleri; Notoedres cati; Notoedres spp.; Oligonychus coffeae; Oligonychus ilicis; Oligonychus spp.; Ornithocheyletia spp.; Ornithonyssus bursa; Ornithonyssus spp.; Ornithonyssus sylviarum; Otodectes cynotis; Otodectes spp.; Panonychus citri; Panonychus spp.; Panonychus ulmi; Phyllocoptruta oleivora; Phyllocoptruta spp.; Phytoseiulus spp.; Pneumonyssoides caninum; Polyphagotarsonemus latus; Polyphagotarsonemus spp.; Psorergates ovis; Psorergates spp.; Psoroptes cuniculi; Psoroptes equi; Psoroptes ovis; Psoroptes spp.; Pterolichus spp.; Raillietia spp.; Rhizoglyphus spp.; Sarcoptes bovis; Sarcoptes canis; Sarcoptes caprae; Sarcoptes equi; Sarcoptes ovis; Sarcoptes rupicaprae; Sarcoptes spp.; Sarcoptes suis; Steneotarsonemus spinki; Steneotarsonemus spp.; Sternostoma spp.; Tarsonemus spp.; Tetranychus cinnabarinus; Tetranychus kanzawai; Tetranychus spp.; Tetranychus urticae; Trombicula akamushi; Trombicula spp.; Typhlodromus occidentalis; Tyrophagus spp.; Varroa jacobsoni; Varroa spp.; Vasates lycopersici; and Zetzellia mali.

In an embodiment, a compound of formula (I) may control one or more of: Aceria sheldoni ; Aculus lycopersici; Aculus pelekassi; Aculus schlechtendali; Brevipalpus phoenicis; Brevipalpus spp.; Bryobia rubrioculus; Eotetranychus carpini; Eotetranychus spp.; Epitrimerus pyri; Eriophyes piri; Eriophyes spp.; Eriophyes vitis; Eutetranychus africanus; Eutetranychus orientalis; Oligonychus pratensis; Panonychus citri; Panonychus ulmi; Phyllocoptes vitis; Phyllocoptruta oleivora; Polyphagotarsonemus latus; Tetranychus cinnabarinus; Tetranychus kanzawai; Tetranychus spp.; and Tetranychus urticae.

In a further embodiment, a compound of formula (I) may especially be suitable for controlling one or more of: Aceria sheldoni; Aculus pelekassi; Brevipalpus phoenicis; Brevipalpus spp.; Eriophyes piri; Eriophyes vitis; Eutetranychus africanus; Eutetranychus orientalis; Oligonychus pratensis; Panonychus ulmi; Phyllocoptes vitis; Phyllocoptruta oleivora; Polyphagotarsonemus latus; Tetranychus cinnabarinus; Tetranychus kanzawai; Tetranychus spp.; and Tetranychus urticae. Toxins that can be expressed by such transgenic plants include, for example, insecticidal proteins, for example insecticidal proteins from Bacillus cereus or Bacillus popilliae; or insecticidal proteins from Bacillus thuringiensis, such as 8-endotoxins, e.g., CrylAb, CrylAc, Cry1 F, Cry1 Fa2, Cry2Ab, Cry3A, Cry3Bb1 or Cry9C, or vegetative insecticidal proteins (Vip), e.g., Vip1 , Vip2, Vip3 or Vip3A; or insecticidal proteins of bacteria colonising nematodes, for example Photorhabdus spp. or Xenorhabdus spp., such as Photorhabdus luminescens, Xenorhabdus nematophilus; toxins produced by animals, such as scorpion toxins, arachnid toxins, wasp toxins and other insect-specific neurotoxins; toxins produced by fungi, such as Streptomycetes toxins, plant lectins, such as pea lectins, barley lectins or snowdrop lectins; agglutinins; proteinase inhibitors, such as trypsin inhibitors, serine protease inhibitors, patatin, cystatin, papain inhibitors; ribosome-inactivating proteins (RIP), such as ricin, maize-RIP, abrin, luffin, saporin or bryodin; steroid metabolism enzymes, such as 3-hydroxysteroidoxidase, ecdysteroid-UDP-glycosyl-transferase, cholesterol oxidases, ecdysone inhibitors, HMG-COA-reductase, ion channel blockers, such as blockers of sodium or calcium channels, juvenile hormone esterase, diuretic hormone receptors, stilbene synthase, bibenzyl synthase, chitinases, and glucanases.

In the context of the present invention there are to be understood by 8-endotoxins, for example CrylAb, CrylAc, Cry1 F, Cry1 Fa2, Cry2Ab, Cry3A, Cry3Bb1 or Cry9C, or vegetative insecticidal proteins (Vip), for example Vi p1 , Vip2, Vip3 or Vip3A, expressly also hybrid toxins, truncated toxins, and modified toxins. Hybrid toxins are produced recombinantly by a new combination of different domains of those proteins (see, for example, WO 02/15701). Truncated toxins, for example a truncated CrylAb, are known. In the case of modified toxins, one or more amino acids of the naturally occurring toxin are replaced. In such amino acid replacements, preferably non-naturally present protease recognition sequences are inserted into the toxin, such as, for example, in the case of Cry3A055, a cathepsin-G-recognition sequence is inserted into a Cry3A toxin (see WO 03/018810).

Examples of such toxins or transgenic plants capable of synthesising such toxins are disclosed, for example, in EP-A-0 374 753, WO 93/07278, WO 95/34656, EP-A-0 427 529, EP-A-451 878 and WO 03/052073.

The processes for the preparation of such transgenic plants are generally known to the person skilled in the art and are described, for example, in the publications mentioned above. Cryl-type deoxyribonucleic acids and their preparation are known, for example, from WO95/34656, EP0367474, EP0401979 and WO90/13651.

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

Transgenic plants containing one or more genes that code for an insecticidal resistance and express one or more toxins are known and some of them are commercially available. Examples of such plants are: YieldGard ® (maize variety that expresses a CrylAb toxin); YieldGard Rootworm® (maize variety that expresses a Cry3Bb1 toxin); YieldGard Plus® (maize variety that expresses a CrylAb and a Cry3Bb1 toxin); Starlink® (maize variety that expresses a Cry9C toxin); Herculex I® (maize variety that expresses a Cry1 Fa2 toxin and the enzyme phosphinothricine N-acetyltransferase (PAT) to achieve tolerance to the herbicide glufosinate ammonium); NuCOTN 33B® (cotton variety that expresses a CrylAc toxin); Bollgard I® (cotton variety that expresses a CrylAc toxin); Bollgard II® (cotton variety that expresses a CrylAc and a Cry2Ab toxin); VipCot ® (cotton variety that expresses a Vip3A and a CrylAb toxin); NewLeaf® (potato variety that expresses a Cry3A toxin); NatureGard®, Agrisure® GT Advantage (GA21 glyphosate-tolerant trait), Agrisure® CB Advantage (Bt11 corn borer (CB) trait) and Protecta®.

Further examples of such transgenic crops are:

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

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

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

4. MON 863 Maize from Monsanto Europe S.A. 270-272 Avenue de Tervuren, B-1150 Brussels, Belgium, registration number C/DE/02/9. MON 863 expresses a Cry3Bb1 toxin and has resistance to certain Coleoptera insects.

5. IPC 531 Cotton from Monsanto Europe S.A. 270-272 Avenue de Tervuren, B-1150 Brussels, Belgium, registration number C/ES/96/02.

6. 1507 Maize from Pioneer Overseas Corporation, Avenue Tedesco, 7 B-1160 Brussels, Belgium, registration number C/NL/00/10. Genetically modified maize for the expression of the protein Cry1 F for achieving resistance to certain Lepidoptera insects and of the PAT protein for achieving tolerance to the herbicide glufosinate ammonium.

7. NK603 x MON 810 Maize from Monsanto Europe S.A. 270-272 Avenue de Tervuren, B-1150 Brussels, Belgium, registration number C/GB/02/M3/03. Consists of conventionally bred hybrid maize varieties by crossing the genetically modified varieties NK603 and MON 810. NK603 x MON 810 Maize transgenically expresses the protein CP4 EPSPS, obtained from Agrobacterium sp. strain CP4, which imparts tolerance to the herbicide Roundup® (contains glyphosate), and also a CrylAb toxin obtained from Bacillus thuringiensis subsp. kurstaki which brings about tolerance to certain Lepidoptera, include the European corn borer. Transgenic crops of insect-resistant plants are also described in BATS (Zentrum fur Biosicherheit und Nachhaltigkeit, Zentrum BATS, Clarastrasse 13, 4058 Basel, Switzerland) Report 2003, (http://bats.ch).

The term "crops" is to be understood as including also crop plants which have been so transformed by the use of recombinant DNA techniques that they are capable of synthesising antipathogenic substances having a selective action, such as, for example, the so-called "pathogenesis-related proteins" (PRPs, see e.g., EP0392225). Examples of such antipathogenic substances and transgenic plants capable of synthesising such antipathogenic substances are known, for example, from EP0392225, WO95/33818 and EP0353191. The methods of producing such transgenic plants are generally known to the person skilled in the art and are described, for example, in the publications mentioned above.

Crops may also be modified for enhanced resistance to fungal (for example Fusarium, Anthracnose, or Phytophthora), bacterial (for example Pseudomonas) or viral (for example potato leafroll virus, tomato spotted wilt virus, cucumber mosaic virus) pathogens.

Crops also include those that have enhanced resistance to nematodes, such as the soybean cyst nematode.

Crops that are tolerance to abiotic stress include those that have enhanced tolerance to drought, high salt, high temperature, chill, frost, or light radiation, for example through expression of NF-YB or other proteins known in the art.

Antipathogenic substances which can be expressed by such transgenic plants include, for example, ion channel blockers, such as blockers for sodium and calcium channels, for example the viral KP1 , KP4 or KP6 toxins; stilbene synthases; bibenzyl synthases; chitinases; glucanases; the so-called "pathogenesis-related proteins" (PRPs; see e.g., EP0392225); antipathogenic substances produced by microorganisms, for example peptide antibiotics or heterocyclic antibiotics (see e.g., WO95/33818) or protein or polypeptide factors involved in plant pathogen defence (so-called "plant disease resistance genes", as described in W003/000906).

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

The present invention provides a compound of the first aspect for use in therapy. The present invention provides a compound of the first aspect, for use in controlling parasites in or on an animal. The present invention further provides a compound of the first aspect, for use in controlling ectoparasites on an animal. The present invention further provides a compound of the first aspect, for use in preventing and/or treating diseases transmitted by ectoparasites. According to this particular aspect of the invention, the use may exclude methods for the treatment of the human or animal body by surgery or therapy.

The present invention provides the use of a compound of the first aspect, for the manufacture of a medicament for controlling parasites in or on an animal. The present invention further provides the use of a compound of the first aspect, for the manufacture of a medicament for controlling ectoparasites on an animal. The present invention further provides the use of a compound of the first aspect, for the manufacture of a medicament for preventing and/or treating diseases transmitted by ectoparasites.

The present invention provides the use of a compound of the first aspect, in controlling parasites in or on an animal. The present invention further provides the use of a compound of the first aspect, in controlling ectoparasites on an animal.

The compounds of the invention may be administered to the animal by any route which has the desired effect including, but not limited to topically, orally, parenterally' and subcutaneously. Topical administration is preferred. Formulations suitable for topical administration include, for example, solutions, emulsions, and suspensions, and may take the form of a pour-on, spot-on, spray-on, spray race or dip. In the alternative, the compounds of the invention may be administered by means of an ear tag or collar.

Salt forms of the compounds of the invention include both pharmaceutically acceptable salts and veterinary acceptable salts, which can be different to agrochemically acceptable salts. Pharmaceutically and veterinary acceptable salts and common methodology for preparing them are well known in the art. See, for example, Gould, P.L., "Salt selection for basic drugs", International Journal of Pharmaceutics, 33: 201 -217 (1986); Bastin, R.J., et al. "Salt Selection and Optimization Procedures for Pharmaceutical New Chemical Entities", Organic Process Research and Development, 4: 427-435 (2000); and Berge, S.M., et al., "Pharmaceutical Salts", Journal of Pharmaceutical Sciences, 66: 1 -19, (1977). One skilled in the art of synthesis will appreciate that the compounds of the invention are readily converted to and may be isolated as a salt, such as a hydrochloride salt, using techniques and conditions well known to one of ordinary skill in the art. In addition, one skilled in the art of synthesis will appreciate that the compounds of the invention are readily converted to and may be isolated as the corresponding free base from the corresponding salt.

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

In one embodiment, the method for controlling such pests comprises applying a pesticidally effective amount of the compositions of the invention to the target pests, to their locus, or to a surface or substrate so as to provide effective residual pesticidal activity on the surface or substrate. Such application may be made by brushing, rolling, spraying, spreading, or dipping the pesticidal composition of the invention. By way of example, an IRS application of a surface such as a wall, ceiling or floor surface is contemplated by the method of the invention so as to provide effective residual pesticidal activity on the surface. In another embodiment, it is contemplated to apply such compositions for residual control of pests on a substrate such as a fabric material in the form of (or which can be used in the manufacture of) netting, clothing, bedding, curtains, and tents. Substrates including non-woven, fabrics or netting to be treated may be made of natural fibres such as cotton, raffia, jute, flax, sisal, hessian, or wool, or synthetic fibres such as polyamide, polyester, polypropylene, polyacrylonitrile or the like. The polyesters are particularly suitable. The methods of textile treatment are known, e.g., WO2008/151984, W02003/034823, US5631072, W02005/64072, W02006/128870, EP1724392, W02005/1 13886, or W02007/090739.

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

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

Table A. Examples of exotic woodborers of economic importance.

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

In particular, the present invention may be used to control insect pests that feed on the roots of turfgrass including white grubs (such as Cyclocephala spp. (e.g., masked chafer, C. lurida), Rhizotrogus spp. (e.g., European chafer, R. majalis), Cotinus spp. (e.g., Green June beetle, C. nitida), Popillia spp. (e.g., Japanese beetle, P. japonica), Phyllophaga spp. (e.g., May/June beetle), Ataenius spp. (e.g., Black turfgrass ataenius, A. spretulus), Maladera spp. (e.g., Asiatic garden beetle, M. castanea) and Tomarus spp.), ground pearls (Margarodes spp.), mole crickets (tawny, southern, and short-winged; Scapteriscus spp., Gryllotalpa africana) and leatherjackets (European crane fly, Tipula spp.).

The present invention may also be used to control insect pests of turfgrass that are thatch dwelling, including armyworms (such as fall armyworm Spodoptera frugiperda, and common armyworm Pseudaletia unipuncta), cutworms, billbugs (Sphenophorus spp., such as S. venatus verstitus and S. parvulus), and sod webworms (such as Crambus spp. and the tropical sod webworm, Herpetogramma phaeopteralis).

The present invention may also be used to control insect pests of turfgrass that live above the ground and feed on the turfgrass leaves, including chinch bugs (such as southern chinch bugs, B/issus insu/aris), Bermudagrass mite (Eriophyes cynodoniensis), rhodesgrass mealybug (Antonina graminis), two-lined spittlebug (Propsapia bicincta), leafhoppers, cutworms (Noctuidae family), and greenbugs.

The present invention may also be used to control other pests of turfgrass such as red imported fire ants (Solenopsis invicta) that create ant mounds in turf.

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

Examples of such parasites are:

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

Of the order Mallophagida: Trimenopon spp., Menopon spp., Trinoton spp., Bovicola spp., Werneckiella spp., Lepikentron spp., Damalina spp., Trichodectes spp. and Felicola spp..

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

Of the order Heteropterida, e.g., Cimex spp., Triatoma spp., Rhodnius spp., Panstrongylus spp..

Of the order Blattarida, e.g., Blatta orientalis, Periplaneta americana, Blattelagermanica and Supella spp..

Of the subclass Acaria (Acarida) and the orders Meta- and Meso-stigmata, e.g., Argas spp., Ornithodorus spp., Otobius spp., Ixodes spp., Amblyomma spp., Boophilus spp., Dermacentor spp., Haemophysalis spp., Hyalomma spp., Rhipicephalus spp., Dermanyssus spp., Raillietia spp., Pneumonyssus spp., Sternostoma spp. and Varroa spp..

Of the orders Actinedida (Prostigmata) and Acaridida (Astigmata), e.g., Acarapis spp., Cheyletiella spp., Ornithocheyletia spp., Myobia spp., Psorergatesspp., Demodex spp., Trombicula spp., Listrophorus spp., Acarus spp., Tyrophagus spp., Caloglyphus spp., Hypodectes spp., Pterolichus spp., Psoroptes spp., Chorioptes spp., Otodectes spp., Sarcoptes spp., Notoedres spp., Knemidocoptes spp., Cytodites spp. and Laminosioptes spp..

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

The compositions according to the invention can be used, for example, against the following pests: beetles such as Hylotrupes bajulus, Chlorophorus pilosis, Anobium punctatum, Xestobium rufovillosum, Ptilinuspecticornis, Dendrobium pertinex, Ernobius mollis, Priobium carpini, Lyctus brunneus, Lyctus africanus, Lyctus planicollis, Lyctus linearis, Lyctus pubescens, Trogoxylon aequale, Minthesrugicollis, Xyleborus spec.,Tryptodendron spec., Apate monachus, Bostrychus capucins, Heterobostrychus brunneus, Sinoxylon spec, and Dinoderus minutus, and also hymenopterans such as Sirex juvencus, Urocerus gigas, Urocerus gigas taignus and Urocerus augur, and termites such as Kalotermes flavicollis, Cryptotermes brevis, Heterotermes indicola, Reticulitermes flavipes, Reticulitermes santonensis, Reticulitermes lucifugus, Mastotermes darwiniensis, Zootermopsis nevadensis and Coptotermes formosanus, and bristletails such as Lepisma saccharina.

The compounds of formula (I), or one compound selected from the group consisting of the compounds as represented in Tables A1 to A6, or a compound listed in Table P (below), or salts thereof, are especially suitable for controlling one or more pests selected from the genus: Spodoptera spp., Helicoverpa spp., Heliothis spp., Leucinodes spp., Tuta spp., Plutella spp., Cydia spp., Lobesia spp., Tortrix spp., Amyelois spp., Maruca spp., Chrysodeixis spp., Agrotis spp., Elasmopalpus spp., Dalbulus spp., Sternechus spp., Phyllotreta spp., Popillia spp., Scirpophaga spp., Chilo spp., Cnaphalocrosis spp., Tetranychus spp., Panonychus spp., Polyphagotarsonemus spp., Phyllocoptruta spp., Aculus spp., Brevipalpus spp., Oligonychus spp., Aculops spp., Nilaparvata spp., Sogatella spp., Laodelphax spp., Nephotettix spp., Diabrotica spp., Agriotes spp., Hypnoidus spp., Limonius spp., Melanotus spp., Conoderus spp., Delia spp., Amphimallon spp., Popillia spp., Euschistus spp., Piezodorus spp., Nezara spp., Dichelops spp., Lygus spp., Leptocorisa spp., Eurygaster spp., Halymorpha spp., Thrips spp., Scirtothrips spp., Frankliniella spp., Anthonomus spp., Melingethes spp., Phyllotreta spp., Leptinotarsa spp., Bemisia spp., Trialeurodes spp., Aphis spp., and Myzus spp.

In a preferred embodiment of each aspect, a compound TX (where the abbreviation “TX” means “one compound selected from the compounds of formula (I), or one compound selected from the group consisting of the compounds as represented in Tables A1 to A6, or a compound listed in Table P (below), controls one or more of pests selected from the genus: Spodoptera spp., Helicoverpa spp., Heliothis spp., Leucinodes spp., Tuta spp., Plutella spp., Cydia spp., Lobesia spp., Tortrix spp., Amyelois spp., Maruca spp., Chrysodeixis spp., Agrotis spp., Elasmopalpus spp., Dalbulus spp., Sternechus spp., Phyllotreta spp., Popillia spp., Scirpophaga spp., Chilo spp., Cnaphalocrosis spp., Tetranychus spp., Panonychus spp., Polyphagotarsonemus spp., Phyllocoptruta spp., Aculus spp., Brevipalpus spp., Oligonychus spp., Aculops spp., Nilaparvata spp., Sogatella spp., Laodelphax spp., Nephotettix spp., Diabrotica spp., Agriotes spp., Hypnoidus spp., Limonius spp., Melanotus spp., Conoderus spp., Delia spp., Amphimallon spp., Popillia spp., Euschistus spp., Piezodorus spp., Nezara spp., Dichelops spp., Lygus spp., Leptocorisa spp., Eurygaster spp., Halymorpha spp., Thrips spp., Scirtothrips spp., Frankliniella spp., Anthonomus spp., Melingethes spp., Phyllotreta spp., Leptinotarsa spp., Bemisia spp., Trialeurodes spp., Aphis spp., and Myzus spp.

The compounds of formula (I), or one compound selected from the group consisting of the compounds as represented in Tables A1 to A6, or a compound listed in Table P (below), or salts thereof, are especially suitable for controlling one or more pests selected from: Spodoptera spp (for example, Spodoptera frugiperda, Spodoptera littoralis), Helicoverpa armigera, Heliothis virescens, Leucinodes orbonalis, Tuta absoluta, Plutella xylostella, Cydia pomonella, Lobesia spp., Tortrix spp., Maruca vitrata, Chrysodeixis includens, Agrotis ipsilon, Elasmopalpus lignosellus, Dalbulus maidis, Phyllotreta spp., Popillia japonica, Scirpophaga incertulas, Chilo suppressalis, Cnaphalocrosis medinalis, Tetranychus urticae, Panonychus ulmi, Polyphagotarsonemus latus, Phyllocoptruta oleivora, Brevipalpus spp., Aculops lycopersici, Nilaparvata lugens, Sogatella frucifera, Laodelphax striatellus, Nephotettix spp., Diabrotica vigifera, Agriotes spp., Hypnoidus bicolor, Limonius canus, Delia radicum, Popillia japonica, Euschistus heros, Piezodorus lituratus, Nezara viridula, Dichelops furcatus, Lygus sp., Leptocorisa acuta, Halyomorpha halys, Thrips tabaci, Scirtothrips dorsalis, Frankliniella occidentalis, Anthonomus grandis, Meligethes aeneus, Phyllotreta spp., Leptinotarsa decemlineata, Bemisia tabaci, Trialeurodes vaporariorum, Aphis gossypii, and Myzus persicae.

In a preferred embodiment of each aspect, a compound TX (where the abbreviation “TX” means “one compound selected from the compounds of formula (I), or one compound selected from the group consisting of the compounds as represented in Tables A1 to A6, or a compound listed in Table P (below)), controls one or more of pests selected from the genus: Spodoptera spp (for example, Spodoptera frugiperda, Spodoptera littoralis) + TX, Helicoverpa armigera + TX, Heliothis virescens + TX, Leucinodes orbonalis + TX, Tuta absoluta + TX, Plutella xylostella + TX, Cydia pomonella + TX, Lobesia spp + TX, Tortrix spp + TX, Maruca vitrata + TX, Chrysodeixis includens + TX, Agrotis ipsilon + TX, Elasmopalpus lignosellus + TX, Dalbulus maidis + TX, Phyllotreta spp + TX, Popillia japonica + TX, Scirpophaga incertulas + TX, Chilo suppressalis + TX, Cnaphalocrosis medinalis + TX, Tetranychus urticae + TX, Panonychus ulmi + TX, Polyphagotarsonemus latus + TX, Phyllocoptruta oleivora + TX Brevipalpus spp + TX, Aculops lycopersici + TX, Nilaparvata lugens + TX, Sogatella frucifera + TX, Laodelphax striatellus + TX, Nephotettix spp + TX, Diabrotica vigifera + TX, Agriotes spp + TX, Hypnoidus bicolor + TX, Limonius canus + TX, Delia radicum + TX, Popillia japonica + TX, Euschistus heros + TX, Piezodorus lituratus + TX, Nezara viridula + TX, Dichelops furcatus + TX, Lygus spp + TX, Leptocorisa acuta + TX, Halyomorpha haly + TX s, Thrips tabaci + TX, Scirtothrips dorsalis + TX, Frankliniella occidentalis + TX, Anthonomus grandis + TX, Meligethes aeneus + TX, Phyllotreta spp + TX, Leptinotarsa decemlineata + TX, Bemisia tabaci + TX, Trialeurodes vaporariorum + TX, Aphis gossypii + TX, and Myzus persicae + TX.

The compounds of formula (I), or one compound selected from the group consisting of the compounds as represented in Tables A1 to A6, or a compound listed in Table P (below), or salts thereof, are especially suitable for controlling in the crops listed in the Table below the pests listed.

# as defined in https://www.ams.usda.aov/services/arants/scbgp/specialtv-crop

In a preferred embodiment of each aspect, a compound TX (where the abbreviation “TX” means “one compound selected from the compounds of formula (I), or one compound selected from the group consisting of the compounds as represented in Tables A1 to A6, or a compound listed in Table P (below)), controls one or more of Spodoptera spp. (for example, Spodoptera frugiperda, Spodoptera littoralis), Helicoverpa armigera, Heliothis virescens, Leucinodes orbonalis, Tuta absoluta, Plutella xylostella, Cydia pomonella, Lobesia spp., Tortrix sp., Maruca vitrata, Chrysodeixis includens, Agrotis ipsilon, Elasmopalpus lignosellus, Dalbulus maidis, Phyllotreta spp., Popillia japonica, Scirpophaga incertulas, Chilo suppressalis, Cnaphalocrosis medinalis, Nilaparvata lugens, Sogatella frucifera, Laodelphax striatellus, Nephotettix spp., Bemisia tabaci, Trialeurodes vaporariorum, Aphis gossypii, and Myzus persicae; such as Spodoptera spp (for example, Spodoptera frugiperda, Spodoptera littoralis) + TX, Helicoverpa armigera + TX, Heliothis virescens + TX, Leucinodes orbonalis + TX, Tuta absoluta + TX, Plutella xylostella + TX, Cydia pomonella + TX, Lobesia spp + TX, Tortrix spp + TX, Maruca vitrata + TX, Chrysodeixis includens + TX, Agrotis ipsilon + TX, Elasmopalpus lignosellus + TX, Dalbulus maidis + TX, Phyllotreta spp + TX, Popillia japonica + TX, Scirpophaga incertulas + TX, Chilo suppressalis + TX, Cnaphalocrosis medinalis + TX, Nilaparvata lugens + TX, Sogatella frucifera + TX, Laodelphax striatellus + TX, Nephotettix spp + TX, Bemisia tabaci + TX, Trialeurodes vaporariorum + TX, Aphis gossypii + TX, and Myzus persicae + TX.

Compounds according to the invention may possess any number of benefits including, inter alia, advantageous levels of biological activity for protecting plants against insects or superior properties for use as agrochemical active ingredients (for example, greater biological activity, an advantageous spectrum of activity, an increased safety profile (against non-target organisms above and below ground (such as fish, birds and bees), improved physico-chemical properties, or increased biodegradability). In particular, it has been surprisingly found that certain compounds of formula (I) may show an advantageous safety profile with respect to non-target arthropods, in particular pollinators such as honey bees, solitary bees, and bumble bees. Most particularly, Apis mellifera.

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

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

The following combinations of a compound of formula (I) with another active substance are preferred (where the abbreviation “TX” means “one compound selected from the compounds of the formulae (I), (I -a), or (l-b), or one compound selected from the group consisting of the compounds as represented in Tables A1 to A2, or a compound listed in Table P (below): (7E,9Z)-dodeca-7,9-dien-1-yl acetate + TX, (9Z,11 E)-tetradeca-9,11-dien- 1-yl acetate + TX, (9Z,12E)-tetradeca-9,12-dien-1-yl acetate + TX, (E)-6-methylhept-2-en-4-ol + TX, (E)-dec- 5-en-1-yl acetate with (E)-dec-5-en-1-ol + TX, (E)-tridec-4-en-1-yl acetate + TX, (E,Z)-tetradeca-4,10-dien-1-yl acetate + TX, (Z)-dodec-7-en-1-yl acetate + TX, (Z)-hexadec-l 1-en-1-yl acetate + TX, (Z)-hexadec-l l-enal + TX, (Z)-hexadec-13-en-1 1-yn-1-yl acetate + TX, (Z)-icos-13-en-10-one + TX, (Z)-tetradec-7-en-1-al + TX, (Z)- tetradec-9-en-1-ol + TX, (Z)-tetradec-9-en-1-yl acetate + TX, 1-(4-chlorophenyl)-2-fluoro-4-methyl-5-(2,2,2- trifluoroethylsulfanyl)benzene + TX, 1 ,2-dibromo-3-chloropropane + TX, 1 ,2-dichloropropane + TX, 1 ,2- dichloropropane with 1 ,3-dichloropropene + TX, 1 ,3-dichloropropene + TX, 14-methyloctadec-1-ene + TX, 1 - hydroxy-1 H-pyridine-2-thione + TX, 2-(octylthio)ethanol + TX, 2-[5-(2-chloro-3,3,3-trifluoro-prop-1-enyl)-1- methyl-imidazol-2-yl]-5-cyclopropyl-3-ethylsulfonyl-pyridine + TX, 2-chlorophenyl N-methylcarbamate (CPMC) + TX, 3-(4-chlorophenyl)-5-methylrhodanine + TX, 3,4-dichlorotetrahydrothiophene 1 ,1-dioxide + TX, 4- (quinoxalin-2-ylamino)benzenesulfonamide + TX, 4-methylnonan-5-ol with 4-methylnonan-5-one + TX, 5- methyl-6-thioxo-1 ,3,5-thiadiazinan-3-ylacetic acid + TX, 6-isopentenylaminopurine + TX, 8-hydroxyquinoline sulfate + TX, abamectin + TX, acequinocyl + TX, acetamiprid + TX, acetoprole + TX, acrinathrin + TX, acynonapyr + TX, Adoxophyes orana GV + TX, afidopyropen + TX, afoxolaner + TX, Agrobacterium radiobacter + TX, AKD-3088 + TX, alanycarb + TX, aldicarb + TX, aldoxycarb + TX, allethrin + TX, alpha-cypermethrin + TX, alphamethrin + TX, alpha-multistriatin + TX, Amblyseius spp. + TX, amidoflumet + TX, amino acids + TX, aminocarb + TX, Anagrapha falcifera NPV + TX, Anagrus atomus + TX, Aphelinus abdominalis + TX, Aphidius colemani + TX, Aphidoletes aphidimyza + TX, apholate + TX, Autographa californica NPV + TX, AZ 60541 + TX, azadirachtin + TX, azocyclotin + TX, Bacillus aizawai + TX, Bacillus chitinosporus AQ746 (NRRL Accession No B-21 618) + TX, Bacillus firmus + TX, Bacillus kurstaki + TX, Bacillus mycoides AQ726 (NRRL Accession No. B-21664) + TX, Bacillus pumilus (NRRL Accession No B-30087) + TX, Bacillus pumilus AQ717 (NRRL Accession No. B-21662) + TX, Bacillus sp. AQ175 (ATCC Accession No. 55608) + TX, Bacillus sp. AQ177 (ATCC Accession No. 55609) + TX, Bacillus sp. AQ178 (ATCC Accession No. 53522) + TX, Bacillus sphaericus Neide + TX, Bacillus subtilis AQ153 (ATCC Accession No. 55614) + TX, Bacillus subtilis AQ30002 (NRRL Accession No. B-50421) + TX, Bacillus subtilis AQ30004 (NRRL Accession No. B- 50455) + TX, Bacillus subtilis AQ713 (NRRL Accession No. B-21661) + TX, Bacillus subtilis AQ743 (NRRL Accession No. B-21665) + TX, Bacillus subtilis unspecified + TX, Bacillus thuringiensis AQ52 (NRRL Accession No. B-21619) + TX, Bacillus thuringiensis BD#32 (NRRL Accession No B-21530) + TX, Bacillus thuringiensis Berliner + TX, Bacillus thuringiensis subsp. Aizawai + TX, Bacillus thuringiensis subsp. Israelensis + TX, Bacillus thuringiensis subsp. Japonensis + TX, Bacillus thuringiensis subsp. Kurstaki + TX, Bacillus thurin-giensis subsp. Tenebrionis + TX, Bacillus thuringiensis subspec. kurstaki BMP 123 + TX, Beauveria bassiana + TX, Beauveria brong n iartii + TX, benclothiaz + TX, benomyl + TX, bensultap + TX, bentioflumin (CAS Number: 2566451 -67-8) + TX, benzoximate + TX, benzpyrimoxan + TX, betacyfluthrin + TX, beta-cypermethrin + TX, bethoxazin + TX, bifenazate + TX, bifenthrin + TX, binapacryl + TX, bioallethrin + TX, bioresmethrin + TX, bis(tributyltin) oxide + TX, bisazir + TX, bistrifluron + TX, bisulflufen + TX, brevicomin + TX, broflanilide + TX, brofluthrinate + TX, bromoacetamide + TX, bromophos-ethyl + TX, bronopol + TX, busulfan + TX, butocarboxim + TX, butopyronoxyl + TX, butoxy(polypropylene glycol) + TX, butylpyridaben + TX, cadusafos + TX, calcium arsenate + TX, carbaryl + TX, carbofuran + TX, carbon disulfide + TX, carbosulfan + TX, cartap + TX, CAS number: 1594624-87-9 + TX, CAS number: 1922957-47-8 + TX, CAS number: 1255091-74-7 + TX, CAS number: 1365070-72-9 + TX, CAS Number: 158062-71-6 + TX, CAS number: 1594626-19-3 + TX, CAS number: 1594637-65-6 + TX, CAS number: 1632218-00-8 + TX, CAS number: 1808115-49-2 + TX, CAS number: 1922957-46-7 + TX, CAS number: 1922957-48-9 + TX, CAS number: 1956329-03-5 + TX, CAS number: 1990457-52-7 + TX, CAS number: 1990457-55-0 + TX, CAS number: 1990457-57-2 + TX, CAS number: 1990457-66-3 + TX, CAS number: 1990457-77-6 + TX, CAS number: 1990457-85-6 + TX, CAS number: 2032403-97-5 + TX, CAS number: 2044701 -44-0 + TX, CAS number: 2095470-94-1 + TX, CAS number: 2128706-05-6 + TX, CAS number: 2133042-31-4 + TX, CAS number: 2133042-44-9 + TX, CAS number: 2171099-09-3 + TX, CAS number: 2220132-55-6 + TX, CAS number: 2396747-83-2 + TX, CAS number: 2408220-91-5 + TX, CAS number: 2408220-94-8 + TX, CAS number: 2415706-16-8 + TX, CAS

Number: 2583740-14-9 + TX, CAS Number: 2583751 -98-6 + TX, CAS number: 2719848-60-7 + TX, CAS Number: 2898489-71-7 + TX, CAS Number: 29221 15-20-4 + TX, CAS Number: 34763-86-5 + TX, CAS number: RNA (Leptinotarsa decemlineata-specific recombinant double-stranded interfering GS2) + TX, chlorantraniliprole + TX, chlordane + TX, chlorfenapyr + TX, chloropicrin + TX, chloroprallethrin + TX, chlorpyrifos + TX, chromafenozide + TX, Chrysoperla carnea + TX, clenpirin + TX, cloethocarb + TX, clothianidin + TX, codlelure + TX, codlemone + TX, copper acetoarsenite + TX, copper dioctanoate + TX, copper hydroxide + TX, copper sulfate + TX, cresol + TX, crufomate + TX, Cryptolaemus montrouzieri + TX, cuelure + TX, cyanofenphos + TX, cyantraniliprole + TX, cybenzoxasulfyl (CAS Number: 2128706-04-5) + TX, cybutryne + TX, cyclaniliprole + TX, cyclobutrifluram + TX, cycloprothrin + TX, cycloxaprid + TX, Cydia pomonella GV + TX, cyenopyrafen + TX, cyetpyrafen + TX, cyflumetofen + TX, cyfluthrin + TX, cyhalodiamide + TX, cylohalothrin + TX, cypermethrin + TX, cyphenothrin + TX, cyproflanilide + TX, cyromazine + TX, cytokinins + TX, Dacnusa sibirica + TX, dazomet + TX, DBCP + TX, DCIP + TX, deltamethrin + TX, diafenthiuron + TX, dialifos + TX, diamidafos + TX, dibrom + TX, dibutyl adipate + TX, dibutyl phthalate + TX, dibutyl succinate + TX, dichlofenthion + TX, dichlone + TX, dichlorophen + TX, dicliphos + TX, dicloromezotiaz + TX, diethyltoluamide + TX, diflubenzuron + TX, Diglyphus isaea + TX, dimatif + TX, dimethoate + TX, dimethyl carbate + TX, dimethyl phthalate + TX, dimpropyridaz + TX, dinactin + TX, dinocap + TX, dinotefuran + TX, dioxabenzofos + TX, dipyrithione + TX, disparlure + TX, D-limonene + TX, dodec-8-en-1-yl acetate + TX, dodec-9-en-1-yl acetate + TX, dodeca-8,10-dien-1-yl acetate + TX, dodicin + TX, dominicalure + TX, doramectin + TX, emamectin + TX, emamectin benzoate + TX, empenthrin + TX, Encarsia formosa + TX, endothal + TX, endrin + TX, eprinomectin + TX, epsilon - momfluorothrin + TX, epsilon-metofluthrin + TX, Eretmocerus eremicus + TX, esfenvalerate + TX, ethion + TX, ethiprole + TX, ethoprophos + TX, ethyl 4- methyloctanoate + TX, ethyl hexanediol + TX, ethylene dibromide + TX, etofenprox + TX, etoxazole + TX, etpyrafen + TX, eugenol + TX, Extract of seaweed and fermentation product derived from melasse + TX, Extract of seaweed and fermentation product derived from melasse comprising urea + TX, Extract of seaweed and fermented plant products + TX, Extract of seaweed and fermented plant products comprising phytohormones, vitamins, EDTA-chelated copper, zinc, and iron + TX, famphur + TX, fenaminosulf + TX, fenamiphos + TX, fenazaquin + TX, fenfluthrin + TX, fenitrothion + TX, fenmezoditiaz + TX, fenobucarb + TX, fenothiocarb + TX, fenoxycarb + TX, fenpropathrin + TX, fenpyrad + TX, fenpyroximate + TX, fensulfothion + TX, fenthion + TX, fentin + TX, fentinacetate + TX, fenvalerate + TX, ferric phosphate + TX, fipronil + TX, flometoquin + TX, flonicamid + TX, fluacrypyrim + TX, fluazaindolizine + TX, fluazuron + TX, flubendiamide + TX, flubenzimine + TX, fluchlordiniliprole + TX, flucitrinate + TX, flucycloxuron + TX, flucythrinate + TX, fluensulfone [318290-98- 1] + TX, fluensulfone + TX, flufenerim + TX, flufenprox + TX, flufiprole + TX, fluhexafon + TX, flumethrin + TX, fluopyram + TX, flupentiofenox + TX, flupyradifurone + TX, flupyrimin + TX, flupyroxystrobin + TX, fluralaner + TX, fluvalinate + TX, fluxametamide + TX, formaldehyde + TX, fosthiazate + TX, fosthietan + TX, frontalin + TX, furfural + TX, galquin (CAS Number: 2644770-30-7) + TX, gamma-cyhalothrin + TX, Gossyplure® (1 :1 mixture of the (Z,E) and (Z,Z) isomers of hexadeca-7,1 1-dien-1-yl-acetate) + TX, grandlure + TX, grandlure I + TX, grandlure II + TX, grandlure III + TX, grandlure IV + TX, Granulovirus + TX, guadipyr + TX, GY -81 + TX, halfenprox + TX, halofenozide + TX, Harpin + TX, Helicoverpa armigera Nucleopolyhedrovirus + TX, Helicoverpa zea NPV + TX, Helicoverpa zea Nucleopolyhedrovirus + TX, Heliothis punctigera Nucleopolyhedrovirus + TX, Heliothis virescens Nucleopolyhedrovirus + TX, hemel + TX, hempa + TX, heptafluthrin + TX, heterophos + TX, Heterorhabditis bacteriophora and H. megidis + TX, hexalure + TX, hexamide + TX, hexythiazox + TX, Hippodamia convergens + TX, hydramethylnon + TX, hydrargaphen + TX, hydrated lime + TX, imicyafos + TX, imidacloprid + TX, imiprothrin + TX, Indazapyroxamet + TX, indoxacarb + TX, iodomethane + TX, iprodione + TX, ipsdienol + TX, ipsenol + TX, isamidofos + TX, isazofos + TX, isocycloseram + TX, Isoflualanam (CAS number: 2892524-05-7) + TX, isothioate + TX, ivermectin + TX, japonilure + TX, kappa-bifenthrin + TX, kappa-tefluthrin + TX, kasugamycin + TX, kasugamycin hydrochloride hydrate + TX, kinetin + TX, lambda-cyhalothrin + TX, ledprona + TX, lepimectin + TX, Leptomastix dactylopii + TX, lineatin + TX, litlure + TX, looplure + TX, lotilaner + TX, lufenuron + TX, Macrolophus caliginosus + TX, Mamestra brassicae NPV + TX, mecarphon + TX, medlure + TX, megatomoic acid + TX, metaflumizone + TX, metaldehyde + TX, metam + TX, metam-potassium + TX, metam-sodium + TX, Metaphycus helvolus + TX, Metarhizium anisopliae var. acridum + TX, Metarhizium anisopliae var. anisopliae + TX, Metarhizium spp. + TX, metepa + TX, methiocarb + TX, methiotepa + TX, methomyl + TX, methoquin-butyl + TX, methoxyfenozide + TX, methyl apholate + TX, methyl bromide + TX, methyl eugenol + TX, methyl isothiocyanate + TX, methylneodecanamide + TX, metofluthrin + TX, metolcarb + TX, mexacarbate + TX, milbemectin + TX, milbemycin oxime + TX, momfluorothrin + TX, morzid + TX, moxidectin + TX, muscalure + TX, Muscodor albus 620 (NRRL Accession No. 30547) + TX, Muscodor roseus A3-5 (NRRL Accession No. 30548) + TX, Myrothecium verrucaria composition + TX, nabam + TX, NC-184 + TX, Neem tree based products + TX, Neodiprion sertifer NPV and N. lecontei NPV + TX, nickel bis(dimethyldithiocarbamate) + TX, niclosamide + TX, niclosamide-olamine + TX, nicofluprole + TX, nitenpyram + TX, nithiazine + TX, nitrapyrin + TX, octadeca- 2,13-dien-1 -yl acetate + TX, octadeca-3,13-dien-1-yl acetate + TX, octhilinone + TX, omethoate + TX, orfralure + TX, Orius spp. + TX, oryctalure + TX, ostramone + TX, oxamate + TX, oxamyl + TX, oxazosulfyl + TX, oxolinic acid + TX, oxytetracycline + TX, Paecilomyces fumosoroseus + TX, Paecilomyces lilacinus + TX, parathion- ethyl + TX, Pasteuria nishizawae + TX, Pasteuria penetrans + TX, Pasteuria ramosa + TX, Pasteuria thornei + TX, Pasteuria usgae + TX, P-cymene + TX, penfluron + TX, pentachlorophenol + TX, permethrin + TX, phenothrin + TX, phorate + TX, phosphamidon + TX, phosphocarb + TX, Phytoseiulus persimilis + TX, picaridin + TX, pioxaniliprole + TX, piperazine + TX, piperflanilide (CAS number: 2615135-05-0) + TX, piperonylbutoxide + TX, pirimicarb + TX, pirimiphos-ethyl + TX, pirimiphos-methyl + TX, Plutella xylostella Granulosis virus + TX, Plutella xylostella Nucleopolyhedrovirus + TX, Polyhedrosis virus + TX, potassium and molybdenum and EDTA-chelated manganese + TX, potassium ethylxanthate + TX, potassium hydroxyquinoline sulfate + TX, prallethrin + TX, probenazole + TX, profenofos + TX, profluthrin + TX, propargite + TX, propetamphos + TX, propoxur + TX, prothiophos + TX, protrifenbute + TX, pyflubumide + TX, pymetrozine + TX, pyraclofos + TX, pyrafluprole + TX, pyrethrum + TX, pyridaben + TX, pyridalyl + TX, pyridin-4-amine + TX, pyrifluquinazon + TX, pyrimidifen + TX, pyriminostrobin + TX, pyriprole [394730-71-3] + TX, pyriprole + TX, pyriproxyfen + TX, QRD 420 (a terpenoid blend) + TX, QRD 452 (a terpenoid blend) + TX, QRD 460 (a terpenoid blend) + TX, Quillaja saponaria + TX, quinoclamine + TX, quinonamid + TX, resmethrin + TX, Rhodococcus globerulus AQ719 (NRRL Accession No B-21663) + TX, sarolaner + TX, S-bioallethrin + TX, sebufos + TX, selamectin + TX, siglure + TX, silafluofen + TX, simazine + TX, sodium pentachlorophenoxide + TX, sordidin + TX, spidoxamat + TX, spinetoram + TX, spinosad + TX, spirobudifen + TX, spirodiclofen + TX, spiromesifen + TX, spiropidion + TX, spirotetramat + TX, Spodoptera exigua multicapsid nuclear polyhedrosis virus + TX, Spodoptera frugiperda Nucleopolyhedrovirus + TX, Steinernema bibionis + TX, Steinernema carpocapsae + TX, Steinernema feltiae + TX, Steinernema glaseri + TX, Steinernema riobrave + TX, Steinernema riobravis + TX, Steinernema scapterisci + TX, Steinernema spp. + TX, Streptomyces galbus (NRRL Accession No. 30232) + TX, Streptomyces sp. (NRRL Accession No. B-30145) + TX, streptomycin + TX, streptomycin sesquisulfate + TX, strychnine + TX, sulcatol + TX, sulfiflumin + TX, sulfoxaflor + TX, tazimcarb + TX, tebufenozide + TX, tebufenpyrad + TX, tebupirimiphos + TX, tecloftalam + TX, tefluthrin + TX, temephos + TX, tepa + TX, terbam + TX, terbufos + TX, terpenoid blend + TX, tetrachlorantraniliprole + TX, tetrachlorothiophene + TX, tetradec- 11-en-1-yl acetate + TX, tetradiphon + TX, tetramethrin + TX, tetramethylfluthrin + TX, tetranactin + TX, tetraniliprole + TX, theta-cypermethrin + TX, thiacloprid + TX, thiafenox + TX, thiamethoxam + TX, thiocyclam + TX, thiodicarb + TX, thiofanox + TX, thiohempa + TX, thiomersal + TX, thiometon + TX, thionazin + TX, thiophanate + TX, thiosultap + TX, thiotepa + TX, tiapyrachlor (CAS Number: 1255091 -74-7) + TX, tigolaner + TX, tiorantraniliprole + TX, tioxazafen + TX, tolfenpyrad + TX, toxaphene + TX, tralomethrin + TX, transfluthrin + TX, tretamine + TX, triazamate + TX, triazophos + TX, triazuron + TX, tributyltin oxide + TX, trichlorfon + TX, trichloronate + TX, trichlorphon + TX, Trichogramma spp. + TX, trifenmorph + TX, trifluenfuronate + TX, triflumezopyrim + TX, trimedlure + TX, trimedlure A + TX, trimedlure B1 + TX, trimedlure B2 + TX, trimedlure C + TX, trimethacarb + TX, triphenyltin acetate + TX, triphenyltin hydroxide + TX, trunc-call + TX, tyclopyrazoflor + TX, Typhlodromus occidentalis + TX, uredepa + TX, Verticillium lecanii + TX, Verticillium spp. + TX, xylenols + TX, YI-5302 + TX, zeatin + TX, zeta-Cypermethrin + TX;

N-[(1 R)-1-benzyl-3-chloro-1-methyl-but-3-enyl]-8-fluoro-quinoline-3-carboxamide + TX, N-[(1 S)-1-benzyl-3- chloro-1-methyl-but-3-enyl]-8-fluoro-quinoline-3-carboxamide + TX, N-ethyl-N’-[5-methoxy-2-methyl-4-[(2- trifuoromethyl)tetrahydrofuran-2-yl]phenyl]-N-methyl-formamidine (these compounds may be prepared from the methods described in WO2019/110427) + TX, (3',4',5'-trifluoro-biphenyl-2-yl)-amide + TX, (3- methylisoxazol-5-yl)-[4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-3-yl]phenyl]methanone (these compounds may be prepared from the methods described in WO 2017/220485) + TX, (4-phenoxyphenyl)methyl 2-amino-6-methyl- pyridine-3-carboxylate (this compound may be prepared from the methods described in WO 2014/006945) + TX, (5-methyl-2-pyridyl)-[4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-3-yl]phenyl]methanone + TX, (7E,9Z)-dodeca- 7,9-dien-1-yl acetate + TX, (9Z,1 1 E)-tetradeca-9,11-dien-1-yl acetate + TX, (9Z,12E)-tetradeca-9,12-dien-1-yl acetate + TX, (E)-6-methylhept-2-en-4-ol + TX, (E)-dec-5-en-1-yl acetate with (E)-dec-5-en-1-ol + TX, (E)- tridec-4-en-1-yl acetate + TX, (E,Z)-tetradeca-4,10-dien-1-yl acetate, + TX, (R)-3-(difluoromethyl)-1-methyl-N- [1 ,1 ,3-trimethylindan-4-yl]pyrazole-4-carboxamide + TX, (Z)-dodec-7-en-1-yl acetate + TX, (Z)-hexadec-l 1-en- 1-yl acetate + TX, (Z)-hexadec-l l-enal + TX, (Z)-hexadec-13-en-1 1-yn-1-yl acetate + TX, (Z)-icos-13-en-1 fl- one + TX, (Z)-tetradec-7-en-1-al + TX, (Z)-tetradec-9-en-1-ol + TX, (Z)-tetradec-9-en-1-yl acetate + TX, (Z,2E)- 5-[1-(2,4-dichlorophenyl)pyrazol-3-yl]oxy-2-methoxyimino-N,3-dimethyl-pent-3-enamide (this compound may be prepared from the methods described in WO 2018/153707) + TX, (Z,2E)-5-[1-(4-chlorophenyl)pyrazol-3- yl]oxy-2-methoxyimino-N,3-dimethyl-pent-3-enamide + TX, , [2-[3-[2-[1-[2-[3,5-bis(difluoromethyl)pyrazol-1- yl]acetyl]-4-piperidyl]thiazol-4-yl]-4,5-dihydroisoxazol-5-yl]-3-chloro-phenyl] methanesulfonate + TX, 1 -(4,5- dimethylbenzimidazol-1 -yl)-4,4,5-trifluoro-3,3-dimethyl-isoquinoline + TX, 1 -(4,5-dimethylbenzimidazol-1-yl)- 4,4-difluoro-3,3-dimethyl-isoquinoline + TX, 1 -(6,7-dimethylpyrazolo[1 ,5-a]pyridin-3-yl)-4,4,5-trifluoro-3,3- dimethyl-isoquinoline + TX, 1 -(6,7-dimethylpyrazolo[1 ,5-a]pyridin-3-yl)-4,4,6-trifluoro-3,3-dimethyl-isoquinoline + TX, 1 -(6-chloro-7-methyl-pyrazolo[1 ,5-a]pyridin-3-yl)-4,4-difluoro-3,3-dimethyl-isoquinoline (these compounds may be prepared from the methods described in WO2017/025510) + TX, 1 ,1-bis(4-chlorophenyl)- 2-ethoxyethanol + TX, 1 ,1 -dichloro-2,2-bis(4-ethylphenyl)ethane + TX, 1 ,2-dibromo-3-chloropropane + TX, 1 ,2- dichloropropane with 1 ,3-dichloropropene + TX, 1 ,3-dichloropropene + TX, 1 ,3-dimethoxy-1-[[4-[5- (trifluoromethyl)-l ,2,4-oxadiazol-3-yl]phenyl]methyl]urea + TX, 1 -[2-[[1-(4-chlorophenyl)pyrazol-3- yl]oxymethyl]-3-methyl-phenyl]-4-methyl-tetrazol-5-one + TX, 10-dien-1 -yl acetate + TX, 14-methyloctadec-1- ene + TX, 1-bromo-2-chloroethane + TX, 1-dichloro-1 -nitroethane + TX, 1 -hydroxy-1 H-pyridine-2-thione + TX, 1-methoxy-3-methyl-1-[[4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-3-yl]phenyl]methyl]urea + TX, 1 -methyl-4-[3- methyl-2-[[2-methyl-4-(3,4,5-trimethylpyrazol-1-yl)phenoxy]methyl]phenyl]tetrazol-5-one + TX, 2- (difluoromethyl) - N- ((3R) - 1 , 1 , 3- trimethylindan- 4- yl) pyridine- 3- carboxamide + TX, 2- (difluoromethyl) - N- ((3R) - 1 , 1 , 3- trimethylindan- 4-yl) pyridine- 3- carboxamide + TX, 2-(1 ,3-dithiolan-2-yl)phenyl dimethylcarbamate + TX, 2-(2-butoxyethoxy)ethyl piperonylate + TX, 2-(2-butoxyethoxy)ethyl thiocyanate + TX, 2-(4,5-dimethyl-1 ,3-dioxolan-2-yl)phenyl methylcarbamate + TX, 2-(4-chloro-3,5-xylyloxy)ethanol + TX, 2- (difluoromethyl)-N-(3-ethyl-1 ,1-dimethyl-indan-4-yl)pyridine-3-carboxamide + TX, 2-(difluoromethyl)-N-[(3R)-3- ethyl-1 ,1-dimethyl-indan-4-yl]pyridine-3-carboxamide + TX, 2-(difluoromethyl)-N-[(3S)-3-ethyl-1 ,1-dimethyl- indan-4-yl]pyridine-3-carboxamide (this compound may be prepared from the methods described in WO 2014/095675) + TX, 2-(difluoromethyl)-N-[3-ethyl-1 ,1 -dimethyl-indan-4-yl]pyridine-3-carboxamide + TX, 2- (octylthio)ethanol + TX, 2,2,2-trichloro-1-(3,4-dichlorophenyl)ethyl acetate + TX, 2,2-dichlorovinyl 2- ethy Isulfinylethy I methyl phosphate + TX, 2,2-difluoro-N-methyl-2-[4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-3- yl]phenyl]acetamide + TX, 2,4-dichlorophenyl benzenesulfonate + TX, 2,6-Dimethyl-1 H,5H-[1 ,4]dithiino[2,3- c:5,6-c']dipyrrole-1 ,3,5,7(2H,6H)-tetrone (this compound may be prepared from the methods described in WO 2011/138281) + TX, 2-[2-fluoro-6-[(8-fluoro-2-methyl-3-quinolyl)oxy]phenyl]propan-2-ol + TX, 2-[6-(4- bromophenoxy)-2-(trifluoromethyl)-3-pyridyl]-1-(1 ,2,4-triazol-1-yl)propan-2-ol (this compound may be prepared from the methods described in WO 2017/029179) + TX, 2-[6-(4-chlorophenoxy)-2-(trifluoromethyl)-3-pyridyl]- 1-(1 ,2,4-triazol-1-yl)propan-2-ol (this compound may be prepared from the methods described in WO 2017/029179) + TX, 2-chlorovinyl diethyl phosphate + TX, 2-fluoro-N-methyl-N-1 -naphthylacetamide + TX, 2- imidazolidone + TX, 2-isovalerylindan-1 ,3-dione + TX, 2-methyl(prop-2-ynyl)aminophenyl methylcarbamate + TX, 2-oxo-N-propyl-2-[4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-3-yl]phenyl]acetamide (this compound may be prepared from the methods described in WO 2018/065414) + TX, 2-thiocyanatoethyl laurate + TX, 3-(4,4- difluoro-3,3-dimethyl-1-isoquinolyl)-7,8-dihydro-6H-cyclopenta[e]benzimidazole (these compounds may be prepared from the methods described in WO2016/156085) + TX, 3-(4,4-difluoro-3,4-dihydro-3,3- dimethylisoquinolin-1-yl)quinolone + TX, 3-(4-chlorophenyl)-5-methylrhodanine + TX, 3-(difluoromethyl)-1- methyl-N-[1 ,1 ,3-trimethylindan-4-yl]pyrazole-4-carboxamide + TX, 3,4-dichlorotetrahydrothiophene 1 ,1-dioxide + TX, 3-[2-(1-chlorocyclopropyl)-3-(2-fluorophenyl)-2-hydroxy-propyl]imidazole-4-carbonitrile (this compound may be prepared from the methods described in WO 2016/156290) + TX, 3-[2-(1-chlorocyclopropyl)-3-(3- chloro-2-fluoro-phenyl)-2-hydroxy-propyl]imidazole-4-carbonitrile (this compound may be prepared from the methods described in WO 2016/156290) + TX, 3-bromo-1 -chloroprop-1 -ene + TX, 3-chloro-6-methyl-5-phenyl-

4-(2,4,6-trifluorophenyl)pyridazine + TX, 3-difluoromethyl-1-methyl-1 H-pyrazole-4-carboxylic acid + TX, 3- ethyl-1-methoxy-1-[[4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-3-yl]phenyl]methyl]urea + TX, 3-methyl-1- phenylpyrazol-5-yl dimethylcarbamate + TX, 4- (2- bromo- 4- fluorophenyl) - N- (2- chloro- 6- fluorophenyl) - 1 ,

3- dimethyl- 1 H- pyrazol- 5- amine + TX, 4-(2,6-difluorophenyl)-6-methyl-5-phenyl-pyridazine-3-carbonitrile + TX, 4-(2-bromo-4-fluoro-phenyl)-N-(2-chloro-6-fluoro-phenyl)-2,5-dimethyl-pyrazol-3-amine + TX, 4- (quinoxalin-2-ylamino)benzenesulfonamide + TX, 4 ,4-di fl u oro-1 -(5-fluoro-4-methyl-benzimidazol-1 -y l)-3 , 3- dimethyl-isoquinoline + TX, 4,4-difluoro-3,3-dimethyl-1 -(6-methylpyrazolo[1 ,5-a]pyridin-3-yl)isoquinoline + TX, 4,4-difluoro-3,3-dimethyl-1-(7-methylpyrazolo[1 ,5-a]pyridin-3-yl)isoquinoline + TX, 4,4-dimethyl-2-[[4-[5- (trifluoromethyl)-l ,2,4-oxadiazol-3-yl]phenyl]methyl]isoxazolidin-3-one + TX, 4-[[6-[2-(2,4-difluorophenyl)-1 ,1- difluoro-2-hydroxy-3-(1 ,2,4-triazol-1-yl)propyl]-3-pyridyl]oxy] benzonitrile + TX, 4-[[6-[2-(2,4-difluorophenyl)- 1 ,1-difluoro-2-hydroxy-3-(5-sulfanyl-1 ,2,4-triazol-1-yl)propyl]-3-pyridyl]oxy] benzonitrile + TX, 4-[[6-[2-(2,4- difluorophenyl)-1 ,1-difluoro-2-hydroxy-3-(5-thioxo-4H-1 ,2,4-triazol-1-yl)propyl]-3-pyridyl]oxy] benzonitrile + TX,

4-chloro-2-(2-chloro-2-methyl-propyl)-5-[(6-iodo-3-pyridyl)methoxy]pyridazin-3-one + TX, 4-chlorophenyl phenyl sulfone + TX, 4-methyl(prop-2-ynyl)amino-3,5-xylyl methylcarbamate + TX, 4-methylnonan-5-ol with 4- methylnonan-5-one + TX, 5-(1 ,3-benzodioxol-5-yl)-3-hexylcyclohex-2-enone + TX, 5,5-dimethyl-2-[[4-[5- (trifluoromethyl)-l ,2,4-oxadiazol-3-yl]phenyl]methyl]isoxazolidin-3-one + TX, 5,5-dimethyl-3-oxocyclohex-1- enyl dimethylcarbamate + TX, 5-amino-1 ,3,4-thiadiazole-2-thiol zinc salt (2:1) + TX, 5-methyl-6-thioxo-1 ,3,5- thiadiazinan-3-ylacetic acid + TX, 6-chloro-3-(3-cyclopropyl-2-fluoro-phenoxy)-N-[2-(2,4-dimethylphenyl)-2,2- difluoro-ethyl]-5-methyl-pyridazine-4-carboxamide (may be prepared from the methods described in WO 2020/109391) + TX, 6-chloro-3-(3-cyclopropyl-2-fluoro-phenoxy)-N-[2-(3,4-dimethylphenyl)-2,2-difluoro-ethyl]-

5-methyl-pyridazine-4-carboxamide (may be prepared from the methods described in WO 2020/109391) + TX,

6-chloro-4,4-difluoro-3,3-dimethyl-1-(4-methylbenzimidazol-1-yl)isoquinoline + TX, 6-chloro-N-[2-(2-chloro-4- methyl-phenyl)-2,2-difluoro-ethyl]-3-(3-cyclopropyl-2-fluoro-phenoxy)-5-methyl-pyridazine-4-carboxamide (may be prepared from the methods described in WO 2020/109391) + TX, 6-ethyl-5,7-dioxo- pyrrolo[4,5][1 ,4]dithiino[1 ,2-c]isothiazole-3-carbonitrile + TX, 6-isopentenylaminopurine + TX, 8-fluoro-N-[(1 R)- 1 -[(3-fluorophenyl)methyl]-1 ,3-dimethyl-butyl]quinoline-3-carboxamide + TX, 8-fluoro-N-[(1 S)-1 -[(3- fluorophenyl)methyl]-1 ,3-dimethyl-butyl]quinoline-3-carboxamide + TX, 8-hydroxyquinoline sulfate + TX, acethion + TX, acetoprole + TX, acibenzolar + TX, acibenzolar-S-methyl + TX, acrylonitrile + TX, Adoxophyes orana GV + TX, Agrobacterium radiobacter + TX, aldoxycarb + TX, aldrin + TX, allosamidin + TX, allyxycarb + TX, alpha-chlorohydrin + TX, alpha-ecdysone + TX, alpha-multistriatin + TX, aluminium phosphide + TX, Amblyseius spp. + TX, amectotractin + TX, ametoctradin + TX, amidithion + TX, amidothioate + TX, aminocarb + TX, aminopyrifen + TX, amisulbrom + TX, amiton + TX, amiton hydrogen oxalate + TX, amitraz + TX, anabasine + TX, Anagrapha falcifera NPV + TX, Anagrus atomus + TX, ancymidol + TX, anilazine + TX, anisiflupurin + TX, anthraquinone + TX, antu + TX, Aphelinus abdominalis + TX, Aphidius colemani + TX, Aphidoletes aphidimyza + TX, apholate + TX, aramite + TX, arsenous oxide + TX, athidathion + TX, Autographa californica NPV + TX, azaconazole + TX, azamethiphos + TX, azobenzene + TX, azothoate + TX, azoxystrobin + TX, Bacillus sphaericus Neide + TX, Bacillus thuringiensis delta endotoxins + TX, barium carbonate + TX, barium hexafluorosilicate + TX, barium polysulfide + TX, barthrin + TX, Bayer 22/190 + TX, Bayer 22408 + TX, Beauveria brongniartii + TX, benalaxyl + TX, benclothiaz + TX, benomyl + TX, benoxafos + TX, benthiavalicarb + TX, benzothiostrobin + TX, benzovindiflupyr + TX, benzyl benzoate + TX, beta-cyfluthrin + TX, beta- cypermethrin + TX, bethoxazin + TX, bioethanomethrin + TX, biopermethrin + TX, bis(2-chloroethyl) ether + TX, bis(tributy Iti n) oxide + TX, bisazir + TX, bisthiosemi + TX, bitertanol + TX, bixafen + TX, blasticidin-S + TX, borax + TX, bordeaux mixture + TX, boscalid + TX, brevicomin + TX, brodifacoum + TX, brofenvalerate + TX, bromadiolone + TX, bromethalin + TX, bromfenvinfos + TX, bromoacetamide + TX, bromocyclen + TX, bromoDDT + TX, bromophos + TX, bromopropylate + TX, bromuconazole + TX, bronopol + TX, bufencarb + TX, bupirimate + TX, buprofezin + TX, busulfan + TX, but-3-ynyl N-[6-[[(Z)-[(1-methyltetrazol-5-yl)-phenyl- methylene]amino]oxymethyl]-2-pyridyl]carbamate + TX, butacarb + TX, butathiofos + TX, butocarboxim + TX, butonate + TX, butopyronoxyl + TX, butoxy(polypropylene glycol) + TX, butoxycarboxim + TX, butylpyridaben + TX, calcium arsenate + TX, calcium cyanide + TX, calcium polysulfide + TX, camphechlor + TX, captafol + TX, captan + TX, carbanolate + TX, carbendazim + TX, carbon disulfide + TX, carbon tetrachloride + TX, carbophenothion + TX, carboxin + TX, cartap hydrochloride + TX, CAS Number: 2454319-63-0 + TX, CAS Number: 83-46-5 + TX, cevadine + TX, chinomethionat + TX, chloralose + TX, chlorbenside + TX, chlorbicyclen + TX, chlordane + TX, chlordecone + TX, chlordimeform + TX, chlordimeform hydrochloride + TX, chlorfenethol + TX, chlorfenson + TX, chlorfensulfide + TX, chlorobenzilate + TX, chloroform + TX, chloroinconazide + TX, chloromebuform + TX, chloromethiuron + TX, chloroneb + TX, chlorophacinone + TX, chloropicrin + TX, chloropropylate + TX, chlorothalonil + TX, chlorphoxim + TX, chlorprazophos + TX, chlorthiophos + TX, chlozolinate + TX, cholecalciferol + TX, Chrysoperla carnea + TX, cinerin I + TX, cinerin II + TX, cinerins + TX, cismethrin + TX, cis-resmethrin + TX, clocythrin + TX, closantel + TX, codlelure + TX, codlemone + TX, copper acetoarsenite + TX, copper arsenate + TX, copper dioctanoate + TX, copper hydroxide + TX, copper naphthenate + TX, copper oleate + TX, copper oxide + TX, copper oxychloride + TX, copper sulfate + TX, coumachlor + TX, coumafuryl + TX, coumaphos + TX, coumatetralyl + TX, coumethoxystrobin (jiaxiangjunzhi) + TX, coumithoate + TX, coumoxystrobin + TX, cresol + TX, crimidine + TX, crotamiton + TX, crotoxyphos + TX, crufomate + TX, cryolite + TX, Cryptolaemus montrouzieri + TX, CS 708 + TX, cuelure + TX, cufraneb + TX, cyanofenphos + TX, cyanophos + TX, cyanthoate + TX, cyazofamid + TX, cybutryne + TX, cyclethrin + TX, cyclobutrifluram + TX, Cydia pomonella GV + TX, cyflufenamid + TX, cymiazole + TX, cymoxanil + TX, cyproconazole + TX, cyprodinil + TX, cythioate + TX, cytokinins + TX, Dacnusa sibirica + TX, DAEP + TX, dazomet + TX, DCIP + TX, DCPM + TX, DDT + TX, debacarb + TX, decarbofuran + TX, demephion + TX, demephion-0 + TX, demephion-S + TX, demeton-methyl + TX, demeton-0 + TX, demeton-O-methyl + TX, demeton-S + TX, demeton-S-methyl + TX, demeton-S-methylsulfon + TX, diamidafos + TX, dibutyl adipate + TX, dibutyl phthalate + TX, dibutyl succinate + TX, dicapthon + TX, dichlobentiazox + TX, dichlofenthion + TX, dichlofluanid + TX, dichlone + TX, dichlorophen + TX, dichlorvos + TX, dichlozoline + TX, dicliphos + TX, diclocymet + TX, diclomezine + TX, dicloran + TX, dicresyl + TX, dicyclanil + TX, dicyclopentadiene + TX, dieldrin + TX, dienochlor + TX, diethofencarb + TX, diethyl 5-methylpyrazol-3-yl phosphate + TX, diethyltoluamide + TX, difenacoum + TX, difenoconazole + TX, difethialone + TX, diflovidazin + TX, Diglyphus isaea + TX, dilor + TX, dimatif + TX, dimefluthrin + TX, dimefox + TX, dimetan + TX, dimethirimol + TX, dimethomorph + TX, dimethrin + TX, dimethyl carbate + TX, dimethyl phthalate + TX, dimethylvinphos + TX, dimetilan + TX, dimoxystrobin + TX, dinex + TX, dinex-diclexine + TX, diniconazole + TX, dinocap-4 + TX, dinocap-6 + TX, dinocton + TX, dinopenton + TX, dinoprop + TX, dinosam + TX, dinoseb + TX, dinosulfon + TX, dinoterbon + TX, diofenolan + TX, dioxabenzofos + TX, dioxathion + TX, diphacinone + TX, diphenyl sulfone + TX, dipymetitrone + TX, dipyrithione + TX, disparlure + TX, disulfiram + TX, dithianon + TX, dithicrofos + TX, DNOC + TX, dodec-8-en-1-yl acetate + TX, dodec-9-en-1-yl acetate + TX, dodeca-8 + TX, dodemorph + TX, dodicin + TX, dodine + TX, dofenapyn + TX, dominicalure + TX, doramectin + TX, DSP + TX, d- tetramethrin + TX, ecdysterone + TX, edifenphos + TX, El 1642 + TX, EMPC + TX, Encarsia formosa + TX, endothal + TX, endothion + TX, enestroburin + TX, enoxastrobin + TX, EPBP + TX, epoxiconazole + TX, eprinomectin + TX, Eretmocerus eremicus + TX, ergocalciferol + TX, etaphos + TX, ethaboxam + TX, ethiofencarb + TX, ethirimol + TX, ethoate-methyl + TX, ethyl 1-[[4-[(Z)-2-ethoxy-3,3,3-trifluoro-prop-1- enoxy]phenyl]methyl]pyrazole-3-carboxylate (may be prepared from the methods described in WO 2020/056090) + TX, ethyl 1 -[[4-[[2-(trifluoromethyl)-1 ,3-dioxolan-2-yl]methoxy]phenyl]methyl]pyrazole-3- carboxylate (may be prepared from the methods described in WO 2020/056090) + TX, ethyl 1 -[[4-[5- (trifluoromethyl)-l ,2,4-oxadiazol-3-yl]phenyl]methyl]pyrazole-4-carboxylate + TX, ethyl 1 -[[5-[5- (trifluoromethyl)-l ,2,4-oxadiazol-3-yl]-2-thienyl]methyl]pyrazole-4-carboxylate (this compound may be prepared from the methods described in WO 2018/158365) + TX, ethyl 4-methyloctanoate + TX, ethyl formate + TX, ethyl hexanediol + TX, ethylene dibromide + TX, ethylene dichloride + TX, ethylene oxide + TX, etridiazole + TX, etrimfos + TX, eugenol + TX, EXD + TX, famoxadone + TX, farnesol + TX, farnesol with nerolidol + TX, fenamidone + TX, fenaminosulf + TX, fenaminstrobin + TX, fenarimol + TX, fenazaflor + TX, fenbuconazole + TX, fenbutatin oxide + TX, fenchlorphos + TX, feneptamidoquin (CAS Number: 2132414-04-9) + TX, fenethacarb + TX, fenfuram + TX, fenhexamid + TX, fenitrothion + TX, fenopyramid (CAS Number: 2344721 - 61-3) + TX, fenothiocarb + TX, fenoxacrim + TX, fenoxanil + TX, fenpiclonil + TX, fenpicoxamid + TX, fenpirithrin + TX, fenpropidin + TX, fenpropimorph + TX, fenpyrad + TX, fenpyrazamine + TX, fenpyroximate + TX, fenson + TX, fensulfothion + TX, fenthion + TX, fenthion-ethyl + TX, fentin + TX, fentrifanil + TX, ferbam + TX, ferimzone + TX, ferric phosphate + TX, flocoumafen + TX, florylpicoxamid + TX, fluazinam + TX, flubeneteram + TX, flubenzimine + TX, flucofuron + TX, flucycloxuron + TX, fludioxonil + TX, fluenetil + TX, flufenoxadiazam + TX, flufenoxystrobin + TX, fluindapyr + TX, flumetylsulforim + TX, flumorph + TX, fluopicolide + TX, fluopimomide + TX, fluopyram + TX, fluorbenside + TX, fluoroacetamide + TX, fluoroimide + TX, fluoxapiprolin + TX, fluoxastrobin + TX, fluoxytioconazole + TX, flupropadine + TX, flupropadine hydrochloride + TX, fluquinconazole + TX, flusilazole + TX, flusulfamide + TX, flutianil + TX, flutolanil + TX, flutriafol + TX, fluxapyroxad + TX, FMC 1137 + TX, folpet + TX, formaldehyde + TX, formetanate + TX, formetanate hydrochloride + TX, formparanate + TX, fosetyl-aluminium + TX, fosmethilan + TX, fospirate + TX, fosthietan + TX, frontalin + TX, fuberidazole + TX, furalaxyl + TX, furametpyr + TX, furathiocarb + TX, furethrin + TX, furfural + TX, gamma-HCH + TX, glyodin + TX, grandlure + TX, grandlure I + TX, grandlure II + TX, grandlure III + TX, grandlure IV + TX, guazatine + TX, guazatine acetates + TX, halfenprox + TX, HCH + TX, hemel + TX, hempa + TX, HEOD + TX, heptachlor + TX, heterophos + TX, Heterorhabditis bacteriophora and H. megidis + TX, hexaconazole + TX, hexadecyl cyclopropanecarboxylate + TX, hexalure + TX, hexamide + TX, HHDN + TX, Hippodamia convergens + TX, hydrargaphen + TX, hydrated lime + TX, hydrogen cyanide + TX, hymexazol + TX, hyquincarb + TX, imanin + TX, imazalil + TX, imibenconazole + TX, iminoctadine + TX, inpyrfluxam + TX, ipconazole + TX, ipfentrifluconazole + TX, ipflufenoquin + TX, iprobenphos + TX, iprodione + TX, iprovalicarb + TX, ipsdienol + TX, ipsenol + TX, IPSP + TX, isamidofos + TX, isazofos + TX, isobenzan + TX, isocarbophos + TX, isodrin + TX, isofenphos + TX, isofetamid + TX, isoflucypram + TX, isolane + TX, isoprothiolane + TX, isopyrazam + TX, isotianil + TX, isoxathion + TX, japonilure + TX, jasmolin I + TX, jasmolin II + TX, jodfenphos + TX, juvenile hormone I + TX, juvenile hormone II + TX, juvenile hormone III + TX, kadethrin + TX, kasugamycin + TX, kasugamycin hydrochloride hydrate + TX, kelevan + TX, kinetin + TX, kinoprene + TX, kresoxim-methyl + TX, lead arsenate + TX, Leptomastix dactylopii + TX, leptophos + TX, lindane + TX, lineatin + TX, lirimfos + TX, litlure + TX, looplure + TX, Ivbenmixianan + TX, lythidathion + TX, Macrolophus caliginosus + TX, magnesium phosphide + TX, malonoben + TX, Mamestra brassicae NPV + TX, mancopper + TX, mancozeb + TX, mandestrobin + TX, mandipropamid + TX, maneb + TX, mazidox + TX, m-cumenyl methylcarbamate + TX, mecarbam + TX, mecarphon + TX, medlure + TX, mefentrifluconazole + TX, megatomoic acid + TX, menazon + TX, mepanipyrim + TX, meperfluthrin + TX, mephosfolan + TX, mepronil + TX, mercuric oxide + TX, mercurous chloride + TX, mesulfen + TX, mesulfenfos + TX, metalaxyl + TX, metam + TX, metam-potassium + TX, metam-sodium + TX, Metaphycus helvolus + TX, Metarhizium anisopliae var. acridum + TX, Metarhizium anisopliae var. anisopliae + TX, metarylpicoxamid + TX, metconazole + TX, metepa + TX, methacrifos + TX, methanesulfonyl fluoride + TX, methasulfocarb + TX, methiotepa + TX, methocrotophos + TX, methoprene + TX, methoquin-butyl + TX, methothrin + TX, methoxychlor + TX, methyl (Z)-2-(5-cyclohexyl-2-methyl-phenoxy)-3-methoxy-prop-2-enoate + TX, methyl (Z)-2-(5-cyclopentyl-2-methyl- phenoxy)-3-methoxy-prop-2-enoate (these compounds may be prepared from the methods described in W02020/193387) + TX, methyl (Z)-2-[5-(3-isopropylpyrazol-1-yl)-2-methyl-phenoxy]-3-methoxy-prop-2-enoate + TX, methyl (Z)-3-methoxy-2-[2-methyl-5-(3-propylpyrazol-1-yl)phenoxy]prop-2-enoate + TX, methyl (Z)-3- methoxy-2-[2-methyl-5-(4-propyltriazol-2-yl)phenoxy]prop-2-enoate + TX, methyl (Z)-3-methoxy-2-[2-methyl-5- [3-(trifluoromethyl)pyrazol-1-yl]phenoxy]prop-2-enoate (these compounds may be prepared from the methods described in W02020/079111) + TX, methyl (Z)-3-methoxy-2-[2-methyl-5-[4-(trifluoromethyl)triazol-2- yl]phenoxy]prop-2-enoate + TX, methyl apholate + TX, methyl bromide + TX, methyl eugenol + TX, methyl isothiocyanate + TX, methyl N-[[4-[1-(2,6-difluoro-4-isopropyl-phenyl)pyrazol-4-yl]-2-methyl- phenyl]methyl]carbamate (may be prepared from the methods described in WO 2020/097012) + TX, methyl N- [[4-[1-(4-cyclopropyl-2,6-difluoro-phenyl)pyrazol-4-yl]-2-methyl-phenyl]methyl]carbamate (may be prepared from the methods described in WO 2020/097012) + TX, methyl N-[[5-[4-(2,4-dimethylphenyl)triazol-2-yl]-2- methyl-phenyl]methyl]carbamate + TX, methylchloroform + TX, methylene chloride + TX, methylneodecanamide + TX, metiram + TX, metolcarb + TX, metomi-nostrobin + TX, metoxadiazone + TX, metrafenone + TX, metyltetraprole + TX, MGK 264 + TX, milbemycin oxime + TX, mipafox + TX, mirex + TX, monocrotophos + TX, morphothion + TX, morzid + TX, moxidectin + TX, muscalure + TX, myclobutanil + TX, myclozoline + TX, Myrothecium verrucaria composition + TX, N-((1 R)-1-benzyl-3-chloro-1-methyl-but-3-enyl)- 8-fluoro-quinoline-3-carboxamide (these compounds may be prepared from the methods described in WO2017/153380) + TX, N-((1 S)-1 -benzyl-3-chloro-1 -methyl-but-3-eny l)-8-fluoro-quinoline-3-carboxamide (these compounds may be prepared from the methods described in WO2017/153380) + TX, N'-(2,5-dimethyl- 4-phenoxy-phenyl)-N-ethyl-N-methyl-formamidine + TX, N'-(2-chloro-5-methyl-4-phenoxy-phenyl)-N-ethyl-N- methyl-formamidine + TX, N,2-dimethoxy-N-[[4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-3- yl]phenyl]methyl]propanamide + TX, N,N-dimethyl-1-[[4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-3- yl]phenyl]methyl]-1 ,2,4-triazol-3-amine (THESE COMPOUNDS may be prepared from the methods described in WO 2017/055473, WO 2017/055469, WO 2017/093348 and WO 2017/118689) + TX, N-[(1 R)-1 -benzyl-1 ,3- dimethyl-butyl]-7,8-difluoro-quinoline-3-carboxamide + TX, N-[(1 R)-1 -benzyl-1 ,3-dimethyl-butyl]-8-fluoro- quinoline-3-carboxamide + TX, N-[(1 R)-1 -benzyl-3,3,3-trifluoro-1 -methyl-propyl]-8-fluoro-quinoline-3- carboxamide + TX, N-[(1 S)-1 -benzyl-1 ,3-dimethyl-butyl]-7,8-difluoro-quinoline-3-carboxamide + TX, N-[(1 S)-1- benzyl-1 ,3-dimethyl-butyl]-8-fluoro-quinoline-3-carboxamide + TX, N-[(1 S)-1-benzyl-3,3,3-trifluoro-1-methyl- propyl]-8-fluoro-quinoline-3-carboxamide + TX, N-[(E)-methoxyiminomethyl]-4-[5-(trifluoromethyl)-1 ,2,4- oxadiazol-3-yl]benzamide + TX, N-[(Z)-methoxyiminomethyl]-4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-3- yl]benzamide + TX, N-[[4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-3-yl]phenyl]methyl]propanamide + TX, N-[2-[2,4- dichloro-phenoxy]phenyl]-3-(difluoromethyl)-1-methyl-pyrazole-4-carboxamide + TX, N-[2-[2-chloro-4- (trifluoromethyl)phenoxy]phenyl]-3-(difluoromethyl)-1-methyl-pyrazole-4-carboxamide + TX, N'-[2-chloro-4-(2- fluorophenoxy)-5-methyl-phenyl]-N-ethyl-N-methyl-formamidine (this compound may be prepared from the methods described in WO 2016/202742) + TX, N'-[4-(4,5-dichlorothiazol-2-yl)oxy-2,5-dimethyl-phenyl]-N-ethyl- N-methyl-formamidine + TX, N'-[5-bromo-2-methyl-6-(1 -methyl-2-propoxy-ethoxy)-3-pyridyl]-N-ethyl-N-methyl- formamidine + TX, N'-[5-bromo-2-methyl-6-(1 -methyl-2-propoxy-ethoxy)-3-pyridyl]-N-isopropyl-N-methyl- formamidine (these compounds may be prepared from the methods described in WO2015/155075) + TX, N'- [5-bromo-2-methyl-6-(2-propoxypropoxy)-3-pyridyl]-N-ethyl-N-methyl-formamidine (this compound may be prepared from the methods described in IPCOM000249876D) + TX, N'-[5-bromo-2-methyl-6-[(1 R)-1-methyl-2- propoxy-ethoxy]-3-pyridyl]-N-ethyl-N-methyl-formamidine + TX, N'-[5-bromo-2-methyl-6-[(1 S)-1-methyl-2- propoxy-ethoxy]-3-pyridyl]-N-ethyl-N-methyl-formamidine + TX, N'-[5-chloro-2-methyl-6-(1-methyl-2-propoxy- ethoxy)-3-pyridyl]-N-ethyl-N-methyl-formamidine + TX, N-[N-methoxy-C-methyl-carbonimidoyl]-4-[5- (trifluoromethyl)-l ,2,4-oxadiazol-3-yl]benzamide (these compounds may be prepared from the methods described in WO 2018/202428) + TX, N’-[4-(1-cyclopropyl-2,2,2-trifluoro-1-hydroxy-ethyl)-5-methoxy-2-methyl- phenyl]-N-isopropyl-N-methyl-formamidine (these compounds may be prepared from the methods described in WO2018/228896) + TX, nabam + TX, naftalofos + TX, naled + TX, naphthalene + TX, NC-170 + TX, Neodiprion sertifer NPV and N. lecontei NPV + TX, nerolidol + TX, N-ethyl-2-methyl-N-[[4-[5-(trifluoromethyl)- 1 ,2,4-oxadiazol-3-yl]phenyl]methyl]propanamide + TX, N-ethyl-N’-[5-methoxy-2-methyl-4-[(2- trifluoromethyl)oxetan-2-yl]phenyl]-N-methyl-formamidine + TX, nickel bis(dimethyldithiocarbamate) + TX, niclosamide-olamine + TX, nicotine + TX, nicotine sulfate + TX, nifluridide + TX, nikkomycins + TX, N-isopropyl- N’-[5-methoxy-2-methyl-4-(2,2,2-trifluoro-1 -hydroxy-1 -pheny l-ethyl)phenyl]-N-methyl-formamidine + TX, nithiazine + TX, nitrapyrin + TX, nitrilacarb + TX, nitrilacarb 1 :1 zinc chloride complex + TX, nitrothal-isopropyl + TX, N-methoxy-N-[[4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-3-yl]phenyl]methyl]cyclopropanecarboxamide + TX, N-methyl-4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-3-yl]benzamide + TX, N-methyl-4-[5-(trifluoromethyl)-1 ,2,4- oxadiazol-3-yl]benzenecarbothioamide + TX, norbormide + TX, nuarimol + TX, O,O,O',O'-tetrapropyl dithiopyrophosphate + TX, octadeca-2,13-dien-1-yl acetate + TX, octadeca-3,13-dien-1-yl acetate + TX, octhilinone + TX, ofurace + TX, oleic acid + TX, omethoate + TX, orfralure + TX, Orius spp. + TX, oryctalure + TX, orysastrobin + TX, ostramone + TX, oxadixyl + TX, oxamate + TX, oxathiapiprolin + TX, oxine-copper + TX, oxolinic acid + TX, oxycarboxin + TX, oxydeprofos + TX, oxydisulfoton + TX, oxytetracycline + TX, paclobutrazole + TX, Paecilomyces fumosoroseus + TX, para-dichlorobenzene + TX, parathion + TX, parathion-methyl + TX, pefurazoate + TX, penconazole + TX, pencycuron + TX, penflufen + TX, penfluron + TX, pentachlorophenol + TX, pentachlorophenyl laurate + TX, penthiopyrad + TX, permethrin + TX, PH 60-38 + TX, phenamacril + TX, phenkapton + TX, phosacetim + TX, phosalone + TX, phosdiphen + TX, phosfolan + TX, phosglycin + TX, phosnichlor + TX, phosphamidon + TX, phosphine + TX, phosphorus + TX, phoximmethyl + TX, phthalide + TX, Phytoseiulus persimilis + TX, picarbutrazox + TX, picaridin + TX, picoxystrobin + TX, pindone + TX, piperazine + TX, piperonyl butoxide + TX, piprotal + TX, pirimetaphos + TX, polychlorodicyclopentadiene isomers + TX, polychloroterpenes + TX, polynactins + TX, polyoxins + TX, potassium arsenite + TX, potassium ethylxanthate + TX, potassium hydroxyquinoline sulfate + TX, potassium thiocyanate + TX, pp'-DDT + TX, precocene I + TX, precocene II + TX, precocene III + TX, primidophos + TX, probenazole + TX, prochloraz + TX, proclonol + TX, procymidone + TX, profluthrin + TX, promacyl + TX, promecarb + TX, propamocarb + TX, propiconazole + TX, propineb + TX, propoxur + TX, propyl isomer + TX, proquinazid + TX, prothidathion + TX, prothioconazole + TX, prothiofos + TX, prothoate + TX, pydiflumetofen + TX, pyraclostrobin + TX, pyrametostrobin + TX, pyraoxystrobin + TX, pyrapropoyne + TX, pyraziflumid + TX, pyrazophos + TX, pyresmethrin + TX, pyrethrin I + TX, pyrethrin II + TX, pyrethrins + TX, pyribencarb + TX, pyridachlometyl + TX, pyridaphenthion + TX, pyridin-4-amine + TX, pyrifenox + TX, pyrimethanil + TX, pyrimitate + TX, pyrimorph + TX, pyrinuron + TX, pyriofenone + TX, pyrisoxazole + TX, pyroquilon + TX, quassia + TX, quinalphos + TX, quinalphos-methyl + TX, quinoclamine + TX, quinofumelin + TX, quinonamid + TX, quinothion + TX, quinoxyfen + TX, quintiofos + TX, quintozene + TX, R-1492 + TX, rafoxanide + TX, resmethrin + TX, Reynoutria sachalinensis extract + TX, ribavirin + TX, R metalaxyl + TX, rotenone + TX, ryania + TX, ryanodine + TX, S421 + TX, sabadilla + TX, schradan + TX, scilliroside + TX, seboctylamine + TX, sebufos + TX, sedaxane + TX, selamectin + TX, sesamex + TX, sesasmolin + TX, SI-0009 + TX, siglure + TX, simazine + TX, simeconazole + TX, sodium arsenite + TX, sodium cyanide + TX, sodium fluoride + TX, sodium fluoroacetate + TX, sodium hexafluorosilicate + TX, sodium pentachlorophenoxide + TX, sodium selenate + TX, sodium tetrathiocarbonate + TX, sodium thiocyanate + TX, sophamide + TX, sordidin + TX, spiroxamine + TX, SSI-121 + TX, Steinernema bibionis + TX, Steinernema carpocapsae + TX, Steinernema feltiae + TX, Steinernema glaseri + TX, Steinernema riobrave + TX, Steinernema riobravis + TX, Steinernema scapterisci + TX, Steinernema spp. + TX, streptomycin + TX, streptomycin sesquisulfate + TX, strychnine + TX, sulcatol + TX, sulcofuron + TX, sulcofuron-sodium + TX, sulfiram + TX, sulfluramid + TX, sulfotep + TX, sulfoxide + TX, sulfur + TX, sulfuryl fluoride + TX, sulprofos + TX, tar oils + TX, tau-fluvalinate + TX, tazimcarb + TX, TDE + TX, tebuconazole + TX, tebufloquin + TX, tebupirimfos + TX, tecloftalam + TX, temephos + TX, tepa + TX, TEPP + TX, terallethrin + TX, terbam + TX, tert-butyl N-[6-[[[(1-methyltetrazol-5-yl)-phenyl- methylene]amino]oxymethyl]-2-pyridyl]carbamate + TX, tetrachloroethane + TX, tetrachlorothiophene + TX, tetraconazole + TX, tetradec-11-en-1-yl acetate + TX, tetradifon + TX, tetramethylfluthrin + TX, tetrasul + TX, thallium sulfate + TX, thiabendazole + TX, thiafenox + TX, thiapronil + TX, thicrofos + TX, thifluzamide + TX, thiocarboxime + TX, thiocyclam + TX, thiocyclam hydrogen oxalate + TX, thiodiazole copper + TX, thiofanox + TX, thiohempa + TX, thiomersal + TX, thiometon + TX, thionazin + TX, thiophanate + TX, thiophanate-methyl + TX, thioquinox + TX, thiosultap + TX, thiosultap-sodium + TX, thiotepa + TX, thiram + TX, thuringiensin + TX, tiadinil + TX, tolclofos-methyl + TX, tolprocarb + TX, toly Ifluanid + TX, tralomethrin + TX, transpermethrin + TX, tretamine + TX, triadimefon + TX, triadimenol + TX, triamiphos + TX, triarathene + TX, triazamate + TX, triazophos + TX, triazoxide + TX, triazuron + TX, tributyltin oxide + TX, trichlormetaphos-3 + TX, trichloronat + TX, Trichogramma spp. + TX, triclopyricarb + TX, tricyclazole + TX, tridemorph + TX, trifenmorph + TX, trifenofos + TX, trifloxystrobin + TX, triflumizole + TX, triforine + TX, trimedlure + TX, trimedlure A + TX, trimedlure B1 + TX, trimedlure B2 + TX, trimedlure C + TX, trimethacarb + TX, trinactin + TX, trinexapac + TX, triphenyltin acetate + TX, triphenyltin hydroxide + TX, triprene + TX, triticonazole + TX, trunc-call + TX, Typhlodromus occidentalis + TX, uredepa + TX, validamycin + TX, valifenalate + TX, vamidothion + TX, vaniliprole + TX, veratridine + TX, veratrine + TX, verbutin + TX, Verticillium lecanii + TX, vinclozoline + TX, warfarin + TX, XMC + TX, xylenols + TX, zeatin + TX, zetamethrin + TX, zhongshengmycin + TX, zinc naphthenate + TX, zinc phosphide + TX, zinc thiazole + TX, zineb + TX, ziram + TX, zolaprofos + TX, zoxamide + TX;

Acinetobacter Iwoffii + TX, Acremonium alternatum + TX, Acremonium cephalosporium + TX, Acremonium diospyri + TX, Acremonium obclavatum + TX, Adoxophyes orana granulovirus (AdoxGV) (Capex®) + TX, Agrobacterium radiobacter strain K84 (Galltrol-A®) + TX, Alternaria alternate + TX, Alternaria cassia + TX, Alternaria destruens (Smolder®) + TX, Ampelomyces quisqualis (AQ10®) + TX, Aspergillus flavus AF36 (AF36®) + TX, Aspergillus flavus NRRL 21882 (Aflaguard®) + TX, Aspergillus spp. + TX, Aureobasidium pullulans + TX, Azospirillum (MicroAZ®, TAZO B®) + TX, Azotobacter + TX, Azotobacter chroocuccum (Azotomeal®) + TX, Azotobacter cysts (Bionatural Blooming Blossoms®) + TX, Bacillus amyloliquefaciens + TX, Bacillus cereus + TX, Bacillus chitinosporus strain AQ746 + TX, Bacillus chitinosporus strain CM-1 + TX, Bacillus circulans + TX, Bacillus firmus (BioSafe®, BioNem-WP®) in particular strain CNMC 1 -1582 (e.g. VOTIVO® from BASF SE) + TX, Bacillus licheniformis strain 3086 (EcoGuard®, Green Releaf®) + TX, Bacillus licheniformis strain HB-2 (Biostart™ formerly Rhizoboost®) + TX, Bacillus macerans + TX, Bacillus marismortui + TX, Bacillus megaterium + TX, Bacillus mycoides strain AQ726 + TX, Bacillus papillae (Milky Spore Powder®) + TX, Bacillus pumilus spp. + TX, Bacillus pumilus strain AQ717 + TX, Bacillus pumilus strain GB34 (Yield Shield®) + TX, Bacillus pumilus strain QST 2808 (Sonata®, Ballad Plus®) + TX, Bacillus sphaericus (VectoLex®) + TX, Bacillus spp. + TX, Bacillus spp. strain AQ175 + TX, Bacillus spp. strain AQ177 + TX, Bacillus spp. strain AQ178 + TX, Bacillus subtilis strain AQ153 + TX, Bacillus subtilis strain AQ743 + TX, Bacillus subtilis strain QST 713 (CEASE®, Serenade®, Rhapsody®) + TX, Bacillus subtilis strain QST 714 (JAZZ®) + TX, Bacillus subtilis strain QST3002 + TX, Bacillus subtilis strain QST3004 + TX, Bacillus subtilis var. amyloliquefaciens strain FZB24 (Taegro®, Rhizopro®) + TX, Bacillus thuringiensis aizawai GC 91 (Agree®) + TX, Bacillus thuringiensis Cry 2Ae + TX, Bacillus thuringiensis Cry1 Ab + TX, Bacillus thuringiensis israelensis (BMP123®, Aquabac®, VectoBac®) + TX, Bacillus thuringiensis kurstaki (Javelin®, Deliver®, CryMax®, Bonide®, Scutella WP®, Turilav WP ®, Astuto®, Dipel WP®, Biobit®, Foray®) + TX, Bacillus thuringiensis kurstaki BMP 123 (Baritone®) + TX, Bacillus thuringiensis kurstaki HD-1 (Bioprotec-CAF I 3P®) + TX, Bacillus thuringiensis strain AQ52 + TX, Bacillus thuringiensis strain BD#32 + TX, Bacillus thuringiensis tenebrionis (Novodor®, BtBooster) + TX, Bacillus thuringiensis var. aizawai (XenTari®, DiPei®) + TX, bacteria spp. (GROWMEND®, GROWSWEET®, Shootup®) + TX, bacteriophage of Clavipacter michiganensis (AgriPhage®, Bakflor®) + TX, Beauveria bassiana (Beaugenic®, Brocaril WP®) + TX, Beauveria bassiana GHA (Mycotrol ES®, Mycotrol O®, BotaniGuard®) + TX, Beauveria brongniartii (Engerlingspilz®, Schweizer Beauveria®, Melocont®) + TX, Beauveria spp. + TX, Botrytis cineria + TX, Bradyrhizobium japonicum (TerraMax®) + TX, Brevibacillus brevis + TX, Burkholderia cepacia (Deny®, Intercept®, Blue Circle®) + TX, Burkholderia gladii + TX, Burkholderia gladioli + TX, Burkholderia spp. + TX, Canadian thistle fungus (CBH Canadian Bioherbicide®) + TX, Candida butyri + TX, Candida famata + TX, Candida fructus + TX, Candida glabrata + TX, Candida guilliermondii + TX, Candida melibiosica + TX, Candida oleophila strain O + TX, Candida parapsilosis + TX, Candida pelliculosa + TX, Candida pulcherrima + TX, Candida reukaufii + TX, Candida saitoana (Bio-Coat®, Biocure®) + TX, Candida sake + TX, Candida spp. + TX, Candida tenius + TX, Cedecea davisae + TX, Cellulomonas flavigena + TX, Chaetomium cochliodes (Nova-Cide®) + TX, Chaetomium globosum (Nova-Cide®) + TX, Chromobacterium subtsugae strain PRAA4-1T (Grandevo®) + TX, Cladosporium chlorocephalum + TX, Cladosporium cladosporioides + TX, Cladosporium oxysporum + TX, Cladosporium spp. + TX, Cladosporium tenuissimum + TX, Clonostachys rosea (EndoFine®) + TX, Colletotrichum acutatum + TX, Coniothyrium minitans (Cotans WG®) + TX, Coniothyrium spp. + TX, Cryptococcus albidus (YIELDPLUS®) + TX, Cryptococcus humicola + TX, Cryptococcus infirmo-miniatus + TX, Cryptococcus laurentii + TX, Cryptophlebia leucotreta granulovirus (Cryptex®) + TX, Cupriavidus campinensis + TX, Cydia pomonella granulovirus (CYD-X®, Madex®, Madex® Plus, Madex Max, Carpovirusine® + TX, Cylindrobasidium laeve (Stumpout®) + TX, Cylindrocladium + TX, Debaryomyces hansenii + TX, Drechslera hawaiinensis + TX, Enterobacter cloacae + TX, Enterobacteriaceae + TX, Entomophtora virulenta (Vektor®) + TX, Epicoccum nigrum + TX, Epicoccum purpurascens + TX, Epicoccum spp. + TX, Filobasidium floriforme + TX, Fusarium acuminatum + TX, Fusarium chlamydosporum + TX, Fusarium oxysporum (Fusaclean®, Biofox C®) + TX, Fusarium proliferatum + TX, Fusarium spp. + TX, Galactomyces geotrichum + TX, Gliocladium catenulatum (Primastop®, Prestop®) + TX, Gliocladium roseum + TX, Gliocladium spp. (SoilGard®) + TX, Gliocladium virens (Soilgard®) + TX, Granulovirus (Granupom®) + TX, Halobacillus halophilus + TX, Halobacillus litoralis + TX, Halobacillus trueperi + TX, Halomonas spp. + TX, Halomonas subglaciescola + TX, Halovibrio variabilis + TX, Hanseniaspora uvarum + TX, Helicoverpa armigera nucleopolyhedrovirus (Helicovex®) + TX, Helicoverpa zea nuclear polyhedrosis virus (Gemstar®) + TX, Isaria fumosorosea (previously known as Paecilomyces fumosoroseus strain, PFR-97®, PreFeRal®) + TX, Isoflavone formononetin (Myconate®) + TX, Kloeckera apiculata + TX, Kloeckera spp. + TX, Lagenidium giganteum (Laginex®) + TX, Lecanicillium lecanii (formerly known as Verticillium lecanii (Mycotal®) conidia of strain KV01 (e.g. Vertalec® by Koppert/Arysta) + TX, Lecanicillium longisporum (Vertiblast®) + TX, Lecanicillium muscarium (Vertikil®) + TX, Lymantria Dispar nucleopolyhedrosis virus (Disparvirus®) + TX, Marinococcus halophilus + TX, Meira geulakonigii + TX, Metarhizium anisopliae (Destruxin WP®) + TX, Metarhizium anisopliae (Met52®) + TX, Metschnikowia fruticola (Shemer®) + TX, Metschnikowia pulcherrima + TX, Microdochium dimerum (Antibot®) + TX, Micromonospora coerulea + TX, Microsphaeropsis ochracea + TX, Muscodor albus 620 (Muscudor®) + TX, Muscodor roseus in particular strain A3-5 (Accession No. NRRL 30548) + TX, Mycorrhizae spp. (AMykor®, Root Maximizer®) + TX, Myrothecium verrucaria strain AARC-0255 (DiTera®, BROS PLUS®) + TX, Ophiostoma piliferum strain D97 (Sylvanex®) + TX, Paecilomyces farinosus + TX, Paecilomyces lilacinus strain 251 (MeloCon WG®) + TX, Paecilomyces linacinus (Biostat WP®) + TX, Paenibacillus polymyxa + TX, Pantoea agglomerans (BlightBan C9-1®) + TX, Pantoea spp. + TX, Pasteuria nishizawae in particular strain Pn1 (CLARIVA from Syngenta/ChemChina); + TX, Pasteuria spp. (Econem®) + TX, Penicillium aurantiogriseum + TX, Penicillium billai (Jumpstart®, TagTeam®) + TX, Penicillium brevicompactum + TX, Penicillium frequentans + TX, Penicillium griseofulvum + TX, Penicillium purpurogenum + TX, Penicillium spp. + TX, Penicillium viridicatum + TX, Phlebiopsis gigantean (Rotstop®) + TX, phosphate solubilizing bacteria (Phosphomeal®) + TX, Phytophthora cryptogea + TX, Phytophthora palmivora (Devine®) + TX, Pichia anomala + TX, Pichia guilliermondii + TX, Pichia membranaefaciens + TX, Pichia onychis + TX, Pichia stipites + TX, Pseudomonas aeruginosa + TX, Pseudomonas aureofasciens (Spot-Less Biofungicide®) + TX, Pseudomonas cepacia + TX, Pseudomonas chlororaphis (AtEze®) + TX, Pseudomonas corrugate + TX, Pseudomonas fluorescens (Zequanox®) + TX, Pseudomonas fluorescens strain A506 (BlightBan A506®) + TX, Pseudomonas putida + TX, Pseudomonas reactans + TX, Pseudomonas spp. + TX, Pseudomonas syringae (Bio-Save®) + TX, Pseudomonas viridiflava + TX, Pseudozyma flocculosa strain PF-A22 UL (Sporodex L®) + TX, Puccinia canaliculata + TX, Puccinia thlaspeos (Wood Warrior®) + TX, Pythium paroecandrum + TX, Pythium oligandrum (Polygandron®, Polyversum®) + TX, Pythium periplocum + TX, Rhanella aquatilis + TX, Rhanella spp. + TX, Rhizobia (Dormal®, Vault®) + TX, Rhizoctonia + TX, Rhodococcus globerulus strain AQ719 + TX, Rhodosporidium diobovatum + TX, Rhodosporidium toruloides + TX, Rhodotorula glutinis + TX, Rhodotorula graminis + TX, Rhodotorula mucilagnosa + TX, Rhodotorula rubra + TX, Rhodotorula spp. + TX, Saccharomyces cerevisiae + TX, Salinococcus roseus + TX, Sclerotinia minor (SARRITOR®) + TX, Sclerotinia minor + TX, Scytalidium spp. + TX, Scytalidium uredinicola + TX, Serratia marcescens + TX, Serratia plymuthica + TX, Serratia spp. + TX, Sordaria fimicola + TX, Spodoptera exigua nuclear polyhedrosis virus (Spod-X®, Spexit®) + TX, Spodoptera littoralis nucleopolyhedrovirus (Littovir®) + TX, Sporobolomyces roseus + TX, Stenotrophomonas maltophilia + TX, Streptomyces albaduncus + TX, Streptomyces exfoliates + TX, Streptomyces galbus + TX, Streptomyces griseoplanus + TX, Streptomyces griseoviridis (Mycostop®) + TX, Streptomyces hygroscopicus + TX, Streptomyces lydicus (Actinovate®) + TX, Streptomyces lydicus WYEC-108 (ActinoGrow®) + TX, Streptomyces violaceus + TX, Tilletiopsis minor + TX, Tilletiopsis spp. + TX, Trichoderma asperellum (T34 Biocontrol®) + TX, Trichoderma atroviride (Plantmate®) + TX, Trichoderma gamsii (Tenet®) + TX, Trichoderma hamatum TH 382 + TX, Trichoderma harzianum rifai (Mycostar®) + TX, Trichoderma harzianum T-22 (Trianum-P®, Plantshield HC®, Rootshield®, Trianum-G® + TX, Trichoderma harzianum T-39 (Trichodex®) + TX, Trichoderma inhamatum + TX, Trichoderma koningii + TX, Trichoderma lignorum + TX, Trichoderma longibrachiatum + TX, Trichoderma polysporum (Binab T®) + TX, Trichoderma spp. LC 52 (Sentinel®) + TX, Trichoderma taxi + TX, Trichoderma virens (formerly Gliocladium virens GL-21) (SoilGuard®) + TX, Trichoderma virens + TX, Trichoderma viride + TX, Trichoderma viride strain ICC 080 (Remedier®) + TX, Trichosporon pullulans + TX, Trichosporon spp. + TX, Trichothecium roseum + TX, Trichothecium spp. + TX, Typhula phacorrhiza strain 94670 + TX, Typhula phacorrhiza strain 94671 + TX, Ulocladium atrum + TX, Ulocladium oudemansii (Botry-Zen®) + TX, Ustilago maydis + TX, various bacteria and supplementary micronutrients (Natural II®) + TX, various fungi (Millennium Microbes®) + TX, Verticillium chlamydosporium + TX, Vip3Aa20 (VIPtera®) + TX, Virgibaclillus marismortui + TX, Xanthomonas campestris pv. Poae (Camperico®) + TX, Xenorhabdus bovienii + TX, Xenorhabdus nematophilus + TX;

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

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

Acerophagus papaya + TX, Adalia bipunctata (Adalia-System®) + TX, Adalia bipunctata (Adaline®) + TX, Adalia bipunctata (Aphidalia®) + TX, Ageniaspis citricola + TX, Ageniaspis fuscicollis + TX, Amblyseius andersoni (Anderline®, Andersoni-System®) + TX, Amblyseius californicus (Amblyline®, Spical®) + TX, Amblyseius cucumeris (Thripex®, Bugline cucumeris®) + TX, Amblyseius fallacis (Fallacis®) + TX, Amblyseius swirskii (Bugline swirskii®, Swirskii-Mite®) + TX, Amblyseius womersleyi (WomerMite®) + TX, Amitus hesperidum + TX, Anagrus atomus + TX, Anagyrus fusciventris + TX, Anagyrus kamali + TX, Anagyrus loecki + TX, Anagyrus pseudococci (Citripar®) + TX, Anicetus benefices + TX, Anisopteromalus calandrae + TX, Anthocoris nemoralis (Anthocoris-System®) + TX, Aphelinus abdominalis (Apheline®, Aphiline®), + TX, Aphelinus asychis + TX, Aphidius colemani (Aphipar®) + TX, Aphidius ervi (Aphelinus-System®) + TX, Aphidius ervi (Ervipar®) + TX, Aphidius gifuensis + TX, Aphidius matricariae (Aphipar-M®) + TX, Aphidoletes aphidimyza (Aphidend®, Aphidoline®) + TX, Aphytis lingnanensis + TX, Aphytis melinus + TX, Aprostocetus hagenowii + TX, Atheta coriaria (Staphyline®) + TX, Bombus spp. + TX, Bombus terrestris (Beeline®, Tripol®) + TX, Bombus terrestris (Natupol Beehive®) + TX, Cephalonomia stephanoderis + TX, Chilocorus nigritus + TX, Chrysoperla carnea (Chrysoline®, Chrysopa®) + TX, Chrysoperla rufilabris + TX, Cirrospilus ingenuus + TX, Cirrospilus quadristriatus + TX, Citrostichus phyllocnistoides + TX, Closterocerus Chamaeleon + TX, Closterocerus spp. + TX, Coccidoxenoides perminutus (Pianopar®) + TX, Coccophagus cowperi + TX, Coccophagus lycimnia + TX, Cotesia flavipes + TX, Cotesia plutellae + TX, Cryptolaemus montrouzieri (Cryptobug®, Cryptoline®) + TX, Cybocephalus nipponicus + TX, Dacnusa sibirica (Minusa®, DacDigline®, Minex®) + TX, Delphastus catalinae (Delphastus®) + TX, Delphastus pusillus + TX, Diachasmimorpha krausii + TX, Diachasmimorpha longicaudata + TX, Diaparsis jucunda + TX, Diaphorencyrtus aligarhensis + TX, Diglyphus isaea (Diminex®, Miglyphus®, Digline®) + TX, Diversinervus spp. + TX, Encarsia citrina + TX, Encarsia formosa (Encarsia max®, Encarline®, En-Strip®) + TX, Encarsia guadeloupae + TX, Encarsia haitiensis + TX, Episyrphus balteatus (Syrphidend®) + TX, Eretmoceris siphonini + TX, Eretmocerus californicus + TX, Eretmocerus eremicus (Enermix®, Ercal®, Eretline e®, Bemimix®) + TX, Eretmocerus hayati + TX, Eretmocerus mundus (Bemipar®, Eretline m®) + TX, Eretmocerus siphonini + TX, Exochomus quadripustulatus + TX, Feltiella acarisuga (Feltiline®) + TX, Feltiella acarisuga (Spidend®) + TX, Fopius arisanus + TX, Fopius ceratitivorus + TX, Formononetin (Wirless Beehome®) + TX, Franklinothrips vespiformis (Vespop®) + TX, Galendromus occidentalis + TX, Goniozus legneri + TX, Habrobracon hebetor + TX, Harmonia axyridis (HarmoBeetle®) + TX, Heterorhabditis bacteriophora (NemaShield HB®, Nemaseek®, Terranem-Nam®, Terranem®, Larvanem®, B-Green®, NemAttack ®, Nematop®) + TX, Heterorhabditis megidis (Nemasys H®, BioNem H®, Exhibitline hm®, Larvanem-M®) + TX, Heterorhabditis spp. (Lawn Patrol®) + TX, Hippodamia convergens + TX, Hypoaspis aculeifer (Aculeifer-System®, Entomite-A®) + TX, Hypoaspis miles (Hypoline m®, Entomite-M®) + TX, Lbalia leucospoides + TX, Lecanoideus floccissimus + TX, Lemophagus errabundus + TX, Leptomastidea abnormis + TX, Leptomastix dactylopii (Leptopar®) + TX, Leptomastix epona + TX, Lindorus lophanthae + TX, Lipolexis oregmae + TX, Lucilia caesar (Natufly®) + TX, Lysiphlebus testaceipes + TX, Macrolophus caliginosus (Mirical-N®, Macroline c®, Mirical®) + TX, Mesoseiulus longipes + TX, Metaphycus flavus + TX, Metaphycus lounsburyi + TX, Micromus angulatus (Milacewing®) + TX, Microterys flavus + TX, Muscidifurax raptorellus and Spalangia cameroni (Biopar®) + TX, Neodryinus typhlocybae + TX, Neoseiulus californicus + TX, Neoseiulus cucumeris (THRYPEX®) + TX, Neoseiulus fallacis + TX, Nesideocoris tenuis (NesidioBug®, Nesibug®) + TX, Ophyra aenescens (Biofly®) + TX, Orius insidiosus (Thripor-I®, Online i®) + TX, Orius laevigatus (Thripor-L®, Online I®) + TX, Orius majusculus (Online m®) + TX, Orius strigicollis (Thripor-S®) + TX, Pauesia juniperorum + TX, Pediobius foveolatus + TX, Phasmarhabditis hermaphrodita (Nemaslug®) + TX, Phymastichus coffea + TX, Phytoseiulus macropilus + TX, Phytoseiulus persimilis (Spidex®, Phytoline p®) + TX, Podisus maculiventris (Podisus®) + TX, Pseudacteon curvatus + TX, Pseudacteon obtusus + TX, Pseudacteon tricuspis + TX, Pseudaphycus maculipennis + TX, Pseudleptomastix mexicana + TX, Psyllaephagus pilosus + TX, Psyttalia concolor (complex) + TX, Quadrastichus spp. + TX, Rhyzobius lophanthae + TX, Rodolia cardinalis + TX, Rumina decollate + TX, Semielacher petiolatus + TX, Sitobion avenae (Ervibank®) + TX, Steinernema carpocapsae (Nematac C®, Millenium®, BioNem C®, NemAttack®, Nemastar®, Capsanem®) + TX, Steinernema feltiae (NemaShield®, Nemasys F®, BioNem F®, Steinernema-System®, NemAttack®, Nemaplus®, Exhibitline st®, Scia-rid®, Entonem®) + TX, Steinernema kraussei (Nemasys L®, BioNem L®, Exhibitline srb®) + TX, Steinernema riobrave (BioVector®, BioVektor®) + TX, Steinernema scapterisci (Nematac S®) + TX, Steinernema spp. + TX, Steinernematid spp. (Guardian Nematodes®) + TX, Stethorus punctillum (Stethorus®) + TX, Tamarixia radiate + TX, Tetrastichus setifer + TX, Thripobius semiluteus + TX, Torymus sinensis + TX, Trichogramma brassicae (Tricholine b®) + TX, Trichogramma brassicae (Tricho-Strip®) + TX, Trichogramma evanescens + TX, Trichogramma minutum + TX, Trichogramma ostriniae + TX, Trichogramma platneri + TX, Trichogramma pretiosum + TX, Xanthopimpla stemmator + TX; abscisic acid + TX, Aminomite® + TX, BioGain® + TX, bioSea® + TX, Chondrostereum purpureum (Chontrol Paste®) + TX, Colletotrichum gloeosporioides (Collego®) + TX, Copper Octanoate (Cueva®) + TX, Delta traps (Trapline d®) + TX, Erwinia amylovora (Harpin) (ProAct®, Ni-HI BIT Gold CST®) + TX, fatty acids derived from a natural by-product of extra virgin olive oil (FLIPPER®) + TX, Ferri-phosphate (Ferramol®) + TX, Funnel traps (Trapline y®) + TX, Gallex® + TX, Grower's Secret® + TX, Homo-brassonolide + TX, Iron Phosphate (Lilly Miller Worry Free Ferramol Slug & Snail Bait®) + TX, MCP hail trap (Trapline f®) + TX, Microctonus hyperodae + TX, Mycoleptodiscus terrestris (Des-X®) + TX, Nosema locustae (Semaspore Organic Grasshopper Control®) + TX, Pheromone trap (Thripline ams®) + TX, potassium bicarbonate (MilStop®) + TX, potassium iodide + potassiumthiocyanate (Enzicur®) + TX, potassium salts of fatty acids (Sanova®) + TX, potassium silicate solution (Sil-Matrix®) + TX, Spider venom + TX, Sticky traps (Trapline YF®, Rebell Amarillo®) + TX, SuffOil-X® + TX, Traps (Takitrapline y + b®) + TX, vadescana (CAS Number: 2643947-26-4) + TX;

Bacillus mojavensis strain R3B (Accession No. NCAIM (P) B001389) (WO 2013/034938) from Certis USA LLC + TX, Bacillus pumilus, in particular strain BU F-33, having NRRL Accession No. 50185 (CARTISSA® from BASF, EPA Reg. No. 71840-19) + TX, Bacillus subtilis CX-9060 from Certis USA LLC, Bacillus sp., in particular strain D747 (available as DOUBLE NICKEL® from Kumiai Chemical Industry Co., Ltd.), having Accession No. FERM BP-8234, U.S. Patent No. 7,094,592 + TX, Bacillus subtilis strain BU1814, (VELONDIS® PLUS, VELONDIS® FLEX and VELONDIS® EXTRA from BASF SE) + TX, Bacillus subtilis var. amyloliquefaciens strain FZB24 having Accession No. DSM 10271 (available from Novozymes as TAEGRO® or TAEGRO® ECO (EPA Registration No. 70127-5)) + TX, Bacillus subtilis, in particular strain QST713/AQ713 (having NRRL Accession No. B-21661 and described in U.S. Patent No. 6,060,051 , available as SERENADE® OPTI or SERENADE® ASO from Bayer CropScience LP, US) + TX, Paenibacillus polymyxa, in particular strain AC-1 (e.g. TOPSEED® from Green Biotech Company Ltd.) + TX, Paenibacillus sp. strain having Accession No. NRRL B-50972 or Accession No. NRRL B-67129, WO 2016/154297 + TX, Pantoea agglomerans, in particular strain E325 (Accession No. NRRL B-21856) (available as BLOOMTIME BIOLOGICAL™ FD BIOPESTICIDE from Northwest Agri Products) + TX, Pseudomonas proradix (e.g. PRORADIX® from Sourcon Padena) + TX;

Aureobasidium pullulans, in particular blastospores of strain DSM14940, blastospores of strain DSM 14941 or mixtures of blastospores of strains DSM14940 and DSM14941 (e.g., BOTECTOR® and BLOSSOM PROTECT® from bio-ferm, CH) + TX, Pseudozyma aphidis (as disclosed in WO2011/151819 by Yissum Research Development Company of the Hebrew University of Jerusalem) + TX, Saccharomyces cerevisiae, in particular strains CNCM No. 1 -3936, CNCM No. 1-3937, CNCM No. 1-3938 or CNCM No. 1-3939 (WO 2010/086790) from Lesaffre et Compagnie, FR + TX;

Agrobacterium radiobacter strain K84 (e.g. GALLTROL-A® from AgBioChem, CA) + TX, Bacillus amyloliquefaciens isolate B246 (e.g. AVOGREEN™ from University of Pretoria) + TX, Bacillus amyloliquefaciens strain F727 (also known as strain MBI110) (NRRL Accession No. B-50768, WO 2014/028521) (STARGUS® from Marrone Bio Innovations) + TX, Bacillus amyloliquefaciens strain FZB42, Accession No. DSM 23117 (available as RHIZOVITAL® from ABiTEP, DE) + TX, Bacillus amyloliquefaciens, in particular strain D747 (available as Double Nickel™ from Kumiai Chemical Industry Co., Ltd., having accession number FERM BP-8234, US Patent No. 7,094,592) + TX, Bacillus licheniformis FMCH001 and Bacillus subtilis FMCH002 (QUARTZO® (WG) and PRESENCE® (WP) from FMC Corporation) + TX, Bacillus licheniformis, in particular strain SB3086, having Accession No. ATCC 55406, WO 2003/000051 (available as ECOGUARD® Biofungicide and GREEN RELEAF™ from Novozymes) + TX, Bacillus methylotrophicus strain BAC-9912 (from Chinese Academy of Sciences’ Institute of Applied Ecology) + TX, Bacillus mycoides, isolate, having Accession No. B-30890 (available as BMJ TGAI® or WG and LifeGard ™ from Certis USA LLC) + TX, Bacillus pumilus, in particular strain GB34 (available as Yield Shield® from Bayer AG, DE) + TX, Bacillus pumilus, in particular strain QST2808 (available as SONATA® from Bayer CropScience LP, US, having Accession No. NRRL B-30087 and described in U.S. Patent No. 6,245,551) + TX, Bacillus subtilis CX-9060 from Certis USA LLC + TX, Bacillus subtilis IAB/BS03 (AVIV™ from STK Bio-Ag Technologies, PORTENTO® from Idai Nature) + TX, Bacillus subtilis KTSB strain (FOLIACTIVE® from Donaghys) + TX, Bacillus subtilis strain BU1814, (available as VELONDIS® PLUS, VELONDIS® FLEX and VELONDIS® EXTRA from BASF SE) + TX, Bacillus subtilis strain GB03 (available as Kodiak® from Bayer AG, DE) + TX, Bacillus subtilis strain MBI 600 (available as SUBTILEX from BASF SE), having Accession Number NRRL B-50595, U.S. Patent No. 5,061 ,495 + TX, Bacillus subtilis strain Y1336 (available as BIOBAC® WP from Bion-Tech, Taiwan, registered as a biological fungicide in Taiwan under Registration Nos. 4764, 5454, 5096 and 5277) + TX, Bacillus subtilis var. amyloliquefaciens strain FZB24 having Accession No. DSM 10271 (available from Novozymes as TAEGRO® or TAEGRO® ECO (EPA Registration No. 70127-5)) + TX, Bacillus subtilis Y1336 (available as BIOBAC® WP from Bion-Tech, Taiwan, registered as a biological fungicide in Taiwan under Registration Nos. 4764, 5454, 5096 and 5277) + TX, Paenibacillus epiphyticus (WO 2016/020371) from BASF SE + TX, Paenibacillus polymyxa ssp. plantarum (WO 2016/020371) from BASF SE + TX, Paenibacillus sp. strain having Accession No. NRRL B-50972 or Accession No. NRRL B-67129, WO 2016/154297 + TX, Pseudomonas chlororaphis strain AFS009, having Accession No. NRRL B-50897, WO 2017/019448 (e.g., HOWLER™ and ZIO® from AgBiome Innovations, US) + TX, Pseudomonas chlororaphis, in particular strain MA342 (e.g. CEDOMON®, CERALL®, and CEDRESS® by Bioagri and Koppert) + TX, Pseudomonas fluorescens strain A506 (e.g. BLIGHTBAN® A506 by NuFarm) + TX, Pseudomonas proradix (e.g. PRORADIX® from Sourcon Padena) + TX, Streptomyces griseoviridis strain K61 (also known as Streptomyces galbus strain K61) (Accession No. DSM 7206) (MYCOSTOP® from Verdera, PREFENCE® from BioWorks, cf. Crop Protection 2006, 25, 468-475) + TX, Streptomyces lydicus strain WYEC108 (also known as Streptomyces lydicus strain WYCD108US) (ACTINO-IRON® and ACTINOVATE® from Novozymes) + TX;

Trichoderma atroviride strain T11 (IMI352941/ CECT20498) + TX, Ampelomyces quisqualis strain AQ10, having Accession No. CNCM 1 -807 (e.g., AQ 10® by IntrachemBio Italia) + TX, Ampelomyces quisqualis, in particular strain AQ 10 (e.g. AQ 10® by IntrachemBio Italia) + TX, Aspergillus flavus strain NRRL 21882 (products known as AFLA-GUARD® from Syngenta/ChemChina) + TX, Aureobasidium pullulans, in particular blastospores of strain DSM 14941 + TX, Aureobasidium pullulans, in particular blastospores of strain DSM14940 + TX, Aureobasidium pullulans, in particular mixtures of blastospores of strains DSM14940 and DSM 14941 (e.g. Botector® by bio-ferm, CH) + TX, Chaetomium cupreum (Accession No. CABI 353812) (e.g. BIOKUPRUM™ by AgriLife) + TX, Chaetomium globosum (available as RIVADIOM® by Rivale) + TX, Cladosporium cladosporioides, strain H39, having Accession No. CBS122244, US 2010/0291039 (by Stichting Dienst Landbouwkundig Onderzoek) + TX, Coniothyrium minitans, in particular strain CON/M/91 -8 (Accession No. DSM9660, e.g. Contans ® from Bayer CropScience Biologies GmbH) + TX, Cryptococcus flavescens, strain 3C (NRRL Y-50378), + TX, Dactylaria Candida, Dilophosphora alopecuri (available as TWIST FUNGUS®), Fusarium oxysporum, strain Fo47 (available as FUSACLEAN® by Natural Plant Protection) + TX, Gliocladium catenulatum (Synonym: Clonostachys rosea f. catenulate) strain J1446 (e.g. Prestop ® by Lallemand) + TX, Gliocladium roseum (also known as Clonostachys rosea f rosea) strain IK726 (Jensen DF, et al. Development of a biocontrol agent for plant disease control with special emphasis on the near commercial fungal antagonist Clonostachys rosea strain ’IK726’, Australasian Plant Pathol. 2007,36(2):95-101) + TX, Gliocladium roseum (also known as Clonostachys rosea f rosea), in particular strain 321 U from Adjuvants Plus, strain ACM941 as disclosed in Xue A.G. (Efficacy of Clonostachys rosea strain ACM941 and fungicide seed treatments for controlling the root tot complex of field pea, Can Jour Plant Sci 2003, 83(3): 519-524) + TX, Metschnikowia fructicola, in particular strain NRRL Y-30752 + TX, Microsphaeropsis ochracea, Penicillium steckii (DSM 27859, WO 2015/067800) from BASF SE + TX, mixtures of Trichoderma asperellum strain ICC 012 (also known as Trichoderma harzianum ICC012), having Accession No. CABI CC IMI 392716 and Trichoderma gamsii (formerly T. viride) strain ICC 080, having Accession No. IMI 392151 (e.g., BIO-TAM™ from Isagro USA, Inc. or BIODERMA® by Agrobiosol de Mexico, S.A. de C.V.) + TX, Penicillium vermiculatum + TX, Phlebiopsis gigantea strain VRA 1992 (ROTSTOP® C from Danstar Ferment) + TX, Pseudozyma flocculosa, strain PF-A22 UL (available as SPORODEX® L by Plant Products Co., CA) + TX, Saccharomyces cerevisiae strain LAS117 cell walls (CEREVISANE® from Lesaffre, ROMEO® from BASF SE) + TX, Saccharomyces cerevisiae strains CNCM No. 1 -3936, CNCM No. 1 -3937, CNCM No. 1-3938, CNCM No. 1- 3939 (WO 2010/086790) from Lesaffre et Compagnie, FR + TX, Saccharomyces cerevisiae, in particular strain LASO2 (from Agro-Levures et Derives) + TX, Simplicillium lanosoniveum + TX, strain T34 (e.g. T34 Biocontrol by Biocontrol Technologies S.L., ES) or strain ICC 012 from Isagro + TX, strain WRL-076 (NRRL Y-30842), U.S. Patent No. 7,579,183 + TX, Talaromyces flavus, strain V117b + TX, Trichoderma asperelloides JM41 R (Accession No. NRRL B-50759) (TRICHO PLUS® from BASF SE) + TX, Trichoderma asperellum, in particular strain SKT-1 , having Accession No. FERM P-16510 (e.g. ECO-HOPE® from Kumiai Chemical Industry) + TX, Trichoderma asperellum, in particular, strain kd (e.g. T-Gro from Andermatt Biocontrol) + TX, Trichoderma atroviride strain 77B (T77 from Andermatt Biocontrol) + TX, Trichoderma atroviride strain ATCC 20476 (IMI

206040) + TX, Trichoderma atroviride strain LC52 (e.g. Tenet by Agrimm Technologies Limited) + TX, Trichoderma atroviride strain LU132 (e.g. Sentinel from Agrimm Technologies Limited) + TX, Trichoderma atroviride strain NMI no. V08/002388 + TX, Trichoderma atroviride strain NMI no. V08/002389 + TX,

Trichoderma atroviride strain NMI no. V08/002390 + TX, Trichoderma atroviride strain no. V08/002387 + TX,

Trichoderma atroviride strain SKT-1 (FERM P-16510), JP Patent Publication (Kokai) 11 -253151 A + TX,

Trichoderma atroviride strain SKT-2 (FERM P-16511), JP Patent Publication (Kokai) 11 -253151 A + TX,

Trichoderma atroviride strain SKT-3 (FERM P-17021), JP Patent Publication (Kokai) 11-253151 A + TX,

Trichoderma atroviride, in particular strain SC1 (Accession No. CBS 122089, WO 2009/116106 and U.S. Patent No. 8,431 ,120 (from Bi-PA)) + TX, Trichoderma atroviride, strain CNCM 1 -1237 (e.g. Esquive® WP from Agrauxine, FR) + TX, Trichoderma fertile (e.g. product TrichoPlus from BASF) + TX, Trichoderma gamsii (formerly T. viride) + TX, Trichoderma gamsii (formerly T. viride) strain ICC 080 (IMI CC 392151 CABI) (available as BIODERMA® by AGROBIOSOL DE MEXICO, S.A. DE C.V.), + TX, Trichoderma gamsii strain ICC080 (IMI CC 392151 CABI, e.g. BioDerma by AGROBIOSOL DE MEXICO, S.A. DE C.V.), + TX, Trichoderma harmatum + TX, Trichoderma harmatum, having Accession No. ATCC 28012 + TX, Trichoderma harzianum + TX, Trichoderma harzianum rifai T39 (e.g. Trichodex® from Makhteshim, US) + TX, Trichoderma harzianum strain Cepa SimbT5 (from Simbiose Agro), + TX, Trichoderma harzianum strain DB 103 (available as T-GRO® 7456 by Dagutat Biolab) + TX, Trichoderma harzianum strain ITEM 908 (e.g. Trianum-P from Koppert) + TX, Trichoderma harzianum strain T-22 (e.g. Trianum-P from Andermatt Biocontrol or Koppert) + TX, Trichoderma harzianum strain TH35 (e.g. Root-Pro by Mycontrol) + TX, Trichoderma polysporum strain IMI 206039 (e.g. Binab TF WP by BINAB Bio-Innovation AB, Sweden) + TX, Trichoderma stromaticum having Accession No. Ts3550 (e.g. Tricovab by CEPLAC, Brazil) + TX, Trichoderma virens (also known as Gliocladium virens) in particular strain GL-21 (e.g. SoilGard by Certis, US) + TX, Trichoderma virens strain G-41 , formerly known as Gliocladium virens (Accession No. ATCC 20906) (e.g., ROOTSHIELD® PLUS WP and TURFSHIELD® PLUS WP from BioWorks, US) + TX, Trichoderma viride in particular strain B35 (Pietr et al., 1993, Zesz. Nauk. A R w Szczecinie 161 : 125-137) + TX, Trichoderma viride strain TV1 (e.g. Trianum-P by Koppert) + TX, Ulocladium oudemansii strain U3, having Accession No. NM 99/06216 (e.g., BOTRY-ZEN® by Botry-Zen Ltd, New Zealand and BOTRYSTOP® from BioWorks, Inc.) + TX, Verticillium albo-atrum (formerly V. dahliae) strain WCS850 having Accession No. WCS850, deposited at the Central Bureau for Fungi Cultures (e.g., DUTCH TRIG® by Tree Care Innovations) + TX, Verticillium chlamydosporium + TX; a mixture of Azotobacter vinelandii and Clostridium pasteurianum (available as INVIGORATE® from Agrinos) + TX, a mixture of Bacillus licheniformis FMCH001 and Bacillus subtilis FMCH002 (available as QUARTZO® (WG), PRESENCE® (WP) from FMC Corporation) + TX, Azorhizobium caulinodans, in particular strain ZB-SK- 5 + TX, Azospirillum brasilense (e.g., VIGOR® from KALO, Inc.) + TX, Azospirillum lipoferum (e.g., VERTEX- IF™ from TerraMax, Inc.) + TX, Azotobacter chroococcum, in particular strain H23 + TX, Azotobacter vinelandii, in particular strain ATCC 12837 + TX, Bacillus amyloliquefaciens BS27 (Accession No. NRRL B-5015) + TX, Bacillus amyloliquefaciens in particular strain FZB42 (e.g. RHIZOVITAL® from ABiTEP, DE) + TX, Bacillus amyloliquefaciens in particular strain IN937a + TX, Bacillus amyloliquefaciens pm414 (LOLI-PEPTA® from Biofilm Crop Protection) + TX, Bacillus amyloliquefaciens SB3281 (ATCC # PTA-7542, WO 2017/205258) + TX, Bacillus amyloliquefaciens TJ1000 (available as QUIKROOTS® from Novozymes) + TX, Bacillus cereus family member EE128 (NRRL No. B-50917) + TX, Bacillus cereus family member EE349 (NRRL No. B-50928) + TX, Bacillus cereus in particular strain BP01 (ATCC 55675, e.g. MEPICHLOR® from Arysta Lifescience, US) + TX, Bacillus mycoides BT155 (NRRL No. B-50921) + TX, Bacillus mycoides BT46-3 (NRRL No. B-50922) + TX, Bacillus mycoides EE118 (NRRL No. B-50918) + TX, Bacillus mycoides EE141 (NRRL No. B-50916) + TX, Bacillus pumilus in particular strain GB34 (e.g. YIELD SHIELD® from Bayer Crop Science, DE), + TX, Bacillus pumilus in particular strain QST2808 (Accession No. NRRL No. B-30087) + TX, Bacillus siamensis in particular strain KCTC 13613T + TX, Bacillus subtilis in particular strain AQ30002 (Accession No. NRRL No. B-50421 and described in U.S. Patent Application No. 13/330,576) + TX, Bacillus subtilis in particular strain AQ30004 (NRRL No. B-50455 and described in U.S. Patent Application No. 13/330,576) + TX, Bacillus subtilis in particular strain MBI 600 (e.g. SUBTILEX® from BASF SE) + TX, Bacillus subtilis rm303 (RHIZOMAX® from Biofilm Crop Protection) + TX, Bacillus subtilis strain BU1814 (available as TEQUALIS® from BASF SE) + TX, Bacillus tequilensis in particular strain NII-0943 + TX, Bacillus thuringiensis BT013A (NRRL No. B-50924) also known as Bacillus thuringiensis 4Q7 + TX, Bradyrhizobium japonicum (e.g. OPTIMIZE® from Novozymes) + TX, Delftia acidovorans in particular strain RAY209 (e.g. BIOBOOST® from Brett Young Seeds) + TX, Lactobacillus sp. (e.g. LACTOPLANT® from LactoPAFI) + TX, Mesorhizobium cicer (e.g., NODULATOR from BASF SE) + TX, Paenibacillus polymyxa in particular strain AC-1 (e.g. TOPSEED® from Green Biotech Company Ltd.) + TX, Pseudomonas aeruginosa in particular strain PN1 + TX, Pseudomonas proradix (e.g. PRORADIX® from Sourcon Padena) + TX, Rhizobium leguminosarium biovar viciae (e.g., NODULATOR from BASF SE) + TX, Rhizobium leguminosarum in particular bv. viceae strain Z25 (Accession No. CECT 4585) + TX, Serratia marcescens in particular strain SRM (Accession No. MTCC 8708), + TX, Sinorhizobium meliloti strain NRG-185-1 (NITRAGIN® GOLD from Bayer CropScience) + TX, Thiobacillus sp. (e.g. CROPAID® from Cropaid Ltd UK) + TX;

Myrothecium verrucaria strain AARC-0255 (e.g. DiTera™ from Valent Biosciences) + TX, Penicillium bilaii strain ATCC 22348 (e.g. JumpStart® from Acceleron BioAg) + TX, Penicillium bilaii strain ATCC ATCC20851 + TX, Purpureocillium lilacinum (previously known as Paecilomyces lilacinus) strain 251 (AGAL 89/030550, e.g. BioAct from Bayer CropScience Biologies GmbH) + TX, Pythium oligandrum strain DV74 + TX, Pythium oligandrum strain M1 (ATCC 38472 e.g. Polyversum from Bioprepraty, CZ) + TX, Rhizopogon amylopogon (Myco-Sol from Agri-Enterprise, LLC, formerly Helena Chemical Company) + TX, Rhizopogon fulvigleba (e.g. Myco-Sol from Agri-Enterprise, LLC, formerly Helena Chemical Company) + TX, Talaromyces flavus strain V117b + TX, Trichoderma asperellum strain (Eco-T from Plant Health Products, ZA) + TX, Trichoderma asperellum strain kd (e.g. T-Gro from Andermatt Biocontrol) + TX, Trichoderma atroviride in particular strain no. V08/002387 + TX, Trichoderma atroviride strain CNCM 1 -1237 (e.g. Esquive® WP from Agrauxine, FR) + TX, Trichoderma atroviride strain LC52 (also known as Trichoderma atroviride strain LU132, e.g. Sentinel from Agrimm Technologies Limited) + TX, Trichoderma atroviride strain no. NMI No. V08/002388 + TX, Trichoderma atroviride strain no. NMI No. V08/002389 + TX, Trichoderma atroviride strain no. NMI No. V08/002390 + TX, Trichoderma atroviride strain SC1 (described in W02009/116106) + TX, Trichoderma harzianum strain 1295- 22 + TX, Trichoderma harzianum strain ITEM 908 + TX, Trichoderma harzianum strain T-22 (e.g. Trianum-P from Andermatt Biocontrol or Koppert) + TX, Trichoderma harzianum strain TSTh20, + TX, Trichoderma virens strain GI-3 + TX, Trichoderma virens strain GL-21 (e.g. SoilGard® from Certis, USA) + TX, Trichoderma viride strain B35 (Pietr et al., 1993, Zesz. Nauk. A R w Szczecinie 161 : 125-137) + TX, Verticillium albo-atrum (formerly V. dahliae) strain WCS850 (CBS 276.92, e.g. Dutch Trig from Tree Care Innovations) + TX;

Agrobacterium radiobacter strain K84 (Galltrol from AgBiochem Inc.), + TX, Bacillus amyloliquefaciens in particular strain PTS-4838 (e.g. AVEO from Valent Biosciences, US), + TX, Bacillus mycoides, isolate J. (e.g. BmJ from Certis USA LLC), + TX, Bacillus sphaericus in particular Serotype H5a5b strain 2362 (strain ABTS- 1743) (e.g. VECTOLEX® from Valent BioSciences, US), + TX, Bacillus thuringiensis israelensis strain BMP 144 (e.g. AQUABAC® by Becker Microbial Products IL) + TX, Bacillus thuringiensis subsp. aizawai strain GC- 91 + TX, Bacillus thuringiensis subsp. aizawai, in particular serotype H-7 (e.g. FLORBAC® WG from Valent BioSciences, US) + TX, Bacillus thuringiensis subsp. aizawai, in particular strain ABTS-1857 (SD-1372, e.g. XENTARI® from Valent BioSciences) + TX, Bacillus thuringiensis subsp. israelensis (serotype H-14) strain AM65-52 (Accession No. ATCC 1276) (e.g. VECTOBAC® by Valent BioSciences, US) + TX, Bacillus thuringiensis subsp. kurstaki strain ABTS 351 + TX, Bacillus thuringiensis subsp. kurstaki strain BMP 123 (from Becker Microbial Products, IL, BARITONE from Bayer CropScience) + TX, Bacillus thuringiensis subsp. kurstaki strain EG 2348 (LEPINOX from Certis, US) + TX, Bacillus thuringiensis subsp. kurstaki strain EG 7841 (CRYMAX from Certis, US) + TX, Bacillus thuringiensis subsp. kurstaki strain HD-1 (e.g. DIPEL® ES from Valent BioSciences, US) + TX, Bacillus thuringiensis subsp. kurstaki strain PB 54 + TX, Bacillus thuringiensis subsp. kurstaki strain SA 11 (JAVELIN from Certis, US) + TX, Bacillus thuringiensis subsp. kurstaki strain SA 12 (THURICIDE from Certis, US) + TX, Bacillus thuringiensis subsp. tenebrionis strain NB 176 (SD-5428, e.g. NOVODOR® FC from BioFa DE) + TX, Bacillus thuringiensis var. Colmeri (e.g. TIANBAOBTC by Changzhou Jianghai Chemical Factory) + TX, Bacillus thuringiensis var. japonensis strain Buibui + TX, Bacillus thuringiensis var. kurstaki strain EVB-113-19 (e.g., BIOPROTEC® from AEF Global) + TX, Brevibacillus laterosporus + TX, Burkholderia spp. in particular Burkholderia rinojensis strain A396 (also known as Burkholderia rinojensis strain MBI 305) (Accession No. NRRL B-50319, WO 2011/106491 and WO 2013/032693, e.g. MBI206 TGAI and ZELTO® from Marrone Bio Innovations), + TX, Chromobacterium subtsugae in particular strain PRAA4-1T (e.g. MBI-203, e.g. GRANDEVO® from Marrone Bio Innovations) + TX, Lecanicillium muscarium Ve6 (MYCOTAL from Koppert) + TX, Paenibacillus popilliae (formerly Bacillus popilliae, e.g. MILKY SPORE POWDER™ or MILKY SPORE GRANULAR™ from St. Gabriel Laboratories) + TX, Serratia entomophila (e.g. INVADE® by Wrightson Seeds) + TX, Serratia marcescens in particular strain SRM (Accession No. MTCC 8708) + TX, Trichoderma asperellum (TRICHODERMAX from Novozymes) + TX, Wolbachia pipientis ZAP strain (e.g., ZAP MALES® from MosquitoMate) + TX;

Beauveria bassiana strain ATCC 74040 (e.g. NATURALIS® from Intrachem Bio Italia) + TX, Beauveria bassiana strain ATP02 (Accession No. DSM 24665), Apopka 97 (PREFERAL from SePRO) + TX, Beauveria bassiana strain GHA (Accession No. ATCC74250, e.g. BOTANIGUARD® ES and MYCONTROL-O® from Laverlam International Corporation) + TX, Metarhizium anisopliae 3213-1 (deposited under NRRL accession number 67074 disclosed in WO 2017/066094, Pioneer Hi-Bred International) + TX, Metarhizium robertsii 15013-1 (deposited under NRRL accession number 67073) + TX, Metarhizium robertsii 23013-3 (deposited under NRRL accession number 67075) + TX, Paecilomyces lilacinus strain 251 (MELOCON from Certis, US) + TX;

Cydia pomonella (codling moth) granulosis virus (GV) + TX, Helicoverpa armigera (cotton bollworm) nuclear polyhedrosis virus (NPV) + TX, of Adoxophyes orana (summer fruit tortrix) granulosis virus (GV) + TX, Spodoptera exigua (beet armyworm) mNPV + TX, Spodoptera frugiperda (fall armyworm) mNPV + TX;

Burkholderia spp. in particular Burkholderia cepacia (formerly known as Pseudomonas cepacia) + TX, Gigaspora spp. + TX, Glomus spp. + TX, Laccaria spp. + TX, LactoBacillus buchneri + TX, Paraglomus spp. + TX, Pisolithus tinctorus + TX, Pseudomonas spp. + TX, Rhizobium spp. in particular Rhizobium trifolii + TX, Rhizopogon spp. + TX, Scleroderma spp. + TX, Streptomyces spp. + TX, Suillus spp. + TX, Agrobacterium spp. + TX, Azorhizobium caulinodans + TX, Azospirillum spp. + TX, Azotobacter spp. + TX, Bradyrhizobium spp. + TX, Gigaspora monosporum + TX;

Allium sativum (NEMGUARD from Eco-Spray, BRALIC from ADAMA) + TX, Armour-Zen + TX, Artemisia absinthium + TX, Biokeeper WP + TX, Brassicaceae extract in particular oilseed rape powder or mustard powder + TX, Cassia nigricans + TX, Celastrus angulatus + TX, Chenopodium anthelminticum + TX, Chenopodium quinoa saponin extract from quinoa seeds (e.g. Heads Up® (Saponins of Quinoa) from Heads Up plant Protectants, CA) + TX, Chitin + TX, Dryopteris filix-mas + TX, Equisetum arvense + TX, Fortune Aza + TX, Fungastop + TX, Melaleuca alternifolia extract (TIMOREX GOLD from STK) + TX, naturally occurring Blad polypeptide extracted from Lupin seeds (FRACTURE® from FMC) + TX, naturally occurring Blad polypeptide extracted from Lupin seeds (PROBLAD® from Certis EU) + TX, Pyrethrins + TX, Quassia amara + TX, Quercus + TX, Quillaja extract (QL AGRI 35 from BASF) + TX, REGALIA MAXX from Marrone Bio) + TX, Requiem™ Insecticide + TX, Reynoutria sachalinensis extract (REGALLIA + TX, ryania/ryanodine + TX, Symphytum officinale + TX, Tanacetum vulgare + TX, Thymol + TX, Thymol mixed with Geraniol (CEDROZ from Eden Research) + TX, Thymol mixed with Geraniol and Eugenol (MEVALONE from Eden Research) + TX, Triact 70 + TX, TriCon + TX, Tropaeulum majus + TX, Urtica dioica + TX, Veratrin + TX, Viscum album + TX; mercuric oxide + TX, octhilinone + TX, thiophanate-methyl + TX;

MGK 264 + TX, 2-(2-butoxyethoxy)ethyl piperonylate + TX, 2-isovalerylindan-1 ,3-dione + TX, 4-(quinoxalin-2- ylamino)benzenesulfonamide + TX, 5-(1 ,3-benzodioxol-5-yl)-3-hexylcyclohex-2-enone + TX, acibenzolar + TX, acibenzolar-S-methyl + TX, alpha-bromadiolone + TX, alpha-chlorohydrin + TX, aluminium phosphide + TX, anthraquinone + TX, antu + TX, arsenous oxide + TX, barium carbonate + TX, benoxacor + TX, bisthiosemi + TX, brodifacoum + TX, bromadiolone + TX, bromethalin + TX, calcium cyanide + TX, chloralose + TX, chlorophacinone + TX, cholecalciferol + TX, cloquintocet (including cloquintocet-mexyl) + TX, copper naphthenate + TX, copper oxychloride + TX, coumachlor + TX, coumafuryl + TX, coumatetralyl + TX, crimidine + TX, cyprosulfamide + TX, diazinon + TX, dichlormid + TX, dicyclopentadiene + TX, difenacoum + TX, difethialone + TX, diphacinone + TX, ergocalciferol + TX, farnesol + TX, farnesol with nerolidol + TX, fenchlorazole (including fenchlorazole-ethyl) + TX, fenclorim + TX, flocoumafen + TX, fluoroacetamide + TX, flupropadine + TX, flupropadine hydrochloride + TX, fluxofenim + TX, furilazole + TX, gamma-HCH + TX, guazatine + TX, guazatine acetates + TX, HCH + TX, hydrogen cyanide + TX, imanin + TX, iodomethane + TX, isoxadifen (including isoxadifen-ethyl) + TX, lindane + TX, magnesium phosphide + TX, MB-599 + TX, mefenpyr (including mefenpyr-diethyl) + TX, metcamifen + TX, methiocarb + TX, methyl bromide + TX, nerolidol + TX, norbormide + TX, petroleum oils + TX, phosacetim + TX, phosphine + TX, phosphorus + TX, pindone + TX, piperonyl butoxide + TX, piprotal + TX, potassium arsenite + TX, probenazole + TX, propyl isomer + TX, pyridin-4-amine + TX, pyrinuron + TX, Reynoutria sachalinensis extract + TX, ribavirin + TX, S421 + TX, scilliroside + TX, sesamex + TX, sesasmolin + TX, sodium arsenite + TX, sodium cyanide + TX, sodium fluoroacetate + TX, strychnine + TX, sulfoxide + TX, thallium sulfate + TX, thiram + TX, trimethacarb + TX, warfarin + TX, zinc naphthenate + TX, zinc phosphide + TX, ziram + TX.

The references in brackets behind the active ingredients, e.g. [3878-19-1] refer to the Chemical Abstracts

Registry number. The above described mixing partners are known. Where the active ingredients are included in "The Pesticide Manual" [The Pesticide Manual - A World Compendium; Thirteenth Edition; Editor: C. D. S.

TomLin; The British Crop Protection Council], they are described therein under the entry number given in round brackets hereinabove for the particular compound; for example, the compound "abamectin" is described under entry number (1). Where "[CCN]" is added hereinabove to the particular compound, the compound in question is included in the "Compendium of Pesticide Common Names", which is accessible on the internet [A. Wood; um of Pesticide Common Names Copyright © 1995-2004]; for example, the compound "acetoprole" is described under the internet address http://www.alanwood.net/pesticides/acetoprole.html.

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

The tradenames in brackets behind the active ingredient refer to the commercially available product or products comprising this active ingredient.

The active ingredient mixture of the compounds of formula (I) selected from the compounds of formulae (I), (I- a), or (l-b), or one compound selected from the group consisting of the compounds as represented in Tables A1 to A2, or a compound listed in Table P (below), with active ingredients described above comprises a compound selected from one compound of formulae (I), (I -a), or (l-b), or one compound selected from the group consisting of the compounds as represented in Tables A1 to A2, or a compound listed in Table P (below), and an active ingredient as described above preferably in a mixing ratio of from 100:1 to 1 :6000, especially from 50:1 to 1 :50, more especially in a ratio of from 20:1 to 1 :20, even more especially from 10:1 to 1 :10, very especially from 5:1 and 1 :5, special preference being given to a ratio of from 2:1 to 1 :2, and a ratio of from 4:1 to 2:1 being likewise preferred, above all in a ratio of 1 :1 , or 5:1 , or 5:2, or 5:3, or 5:4, or 4:1 , or 4:2, or 4:3, or 3:1 , or 3:2, or 2:1 , or 1 :5, or 2:5, or 3:5, or 4:5, or 1 :4, or 2:4, or 3:4, or 1 :3, or 2:3, or 1 :2, or 1 :600, or 1 :300, or 1 :150, or 1 :35, or 2:35, or 4:35, or 1 :75, or 2:75, or 4:75, or 1 :6000, or 1 :3000, or 1 :1500, or 1 :350, or 2:350, or 4:350, or 1 :750, or 2:750, or 4:750. Those mixing ratios are by weight.

The mixtures as described above can be used in a method for controlling pests, which comprises applying a composition comprising a mixture as described above to the pests or their environment, with the exception of a method for treatment of the human or animal body by surgery or therapy and diagnostic methods practised on the human or animal body.

The mixtures comprising a compound of formula (I) selected from the compounds of formulae (I), (l-a), or (l-b), or one compound selected from the group consisting of the compounds as represented in Tables A1 to A2, or a compound listed in Table P (below), and one or more active ingredients as described above can be applied, for example, in a single “ready-mix” form, in a combined spray mixture composed from separate formulations of the single active ingredient components, such as a “tank-mix”, and in a combined use of the single active ingredients when applied in a sequential manner, e.g., one after the other with a reasonably short period, such as a few hours or days. The order of applying the compounds of formula (I) and the active ingredients as described above is not essential for working the present invention.

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

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

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

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

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

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

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

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

The compounds of the invention can be distinguished from other similar compounds by virtue of greater efficacy at low application rates and/or different pest control, which can be verified by the person skilled in the art using the experimental procedures, using lower concentrations if necessary, e.g., 10 ppm, 5 ppm, 2 ppm, 1 ppm or 0.2 ppm; or lower application rates, such as 300, 200 or 100, mg of Al (active ingredient) per m². The greater efficacy can be observed by an increased safety profile (against non-target organisms above and below ground (such as fish, birds, and bees), improved physico-chemical properties, or increased biodegradability).

In each aspect and embodiment of the invention, "consisting essentially" and inflections thereof are a preferred embodiment of "comprising" and its inflections, and "consisting of and inflections thereof are a preferred embodiment of "consisting essentially of and its inflections. The disclosure in the present application makes available each and every combination of embodiments disclosed herein.

It should be noted that the disclosure herein in respect of a compound of formula (I) applies equally in respect of a compound of each of formula (I), or one compound selected from the group consisting of the compounds as represented in Tables A1 to A6, or a compound listed in Table P (below),

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

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

The active ingredients can also be contained in very fine microcapsules. Microcapsules contain the active ingredients in a porous carrier. This enables the active ingredients to be released into the environment in controlled amounts (e.g., slow-release). Microcapsules usually have a diameter of from 0.1 to 500 microns. They contain active ingredients in an amount of about from 25 to 95 % by weight of the capsule weight. The active ingredients can be in the form of a monolithic solid, in the form of fine particles in solid or liquid dispersion or in the form of a suitable solution. The encapsulating membranes can comprise, for example, natural or synthetic rubbers, cellulose, styrene/butadiene copolymers, polyacrylonitrile, polyacrylate, polyesters, polyamides, polyureas, polyurethane or chemically modified polymers and starch xanthates or other polymers that are known to the person skilled in the art. Alternatively, very fine microcapsules can be formed in which the active ingredient is contained in the form of finely divided particles in a solid matrix of base substance, but the microcapsules are not themselves encapsulated.

The formulation adjuvants that are suitable for the preparation of the compositions according to the invention are known perse. As liquid carriers there may be used: water, toluene, xylene, petroleum ether, vegetable oils, acetone, methyl ethyl ketone, cyclohexanone, acid anhydrides, acetonitrile, acetophenone, amyl acetate, 2- butanone, butylene carbonate, chlorobenzene, cyclohexane, cyclohexanol, alkyl esters of acetic acid, diacetone alcohol, 1 ,2-dichloropropane, diethanolamine, p-diethylbenzene, diethylene glycol, diethylene glycol abietate, diethylene glycol butyl ether, diethylene glycol ethyl ether, diethylene glycol methyl ether, IV, IV- dimethylformamide, dimethyl sulfoxide, 1 ,4-dioxane, dipropylene glycol, dipropylene glycol methyl ether, dipropylene glycol dibenzoate, diproxitol, alkylpyrrolidone, ethyl acetate, 2-ethylhexanol, ethylene carbonate, 1 ,1 ,1 -trichloroethane, 2-heptanone, alpha-pinene, d-limonene, ethyl lactate, ethylene glycol, ethylene glycol butyl ether, ethylene glycol methyl ether, gamma-butyrolactone, glycerol, glycerol acetate, glycerol diacetate, glycerol triacetate, hexadecane, hexylene glycol, isoamyl acetate, isobornyl acetate, isooctane, isophorone, isopropylbenzene, isopropyl myristate, lactic acid, laurylamine, mesityl oxide, methoxypropanol, methyl isoamyl ketone, methyl isobutyl ketone, methyl laurate, methyl octanoate, methyl oleate, methylene chloride, m-xylene, n-hexane, n-octylamine, octadecanoic acid, octylamine acetate, oleic acid, oleylamine, o-xylene, phenol, polyethylene glycol, propionic acid, propyl lactate, propylene carbonate, propylene glycol, propylene glycol methyl ether, p-xylene, toluene, triethyl phosphate, triethylene glycol, xylenesulfonic acid, paraffin, mineral oil, trichloroethylene, perchloroethylene, ethyl acetate, amyl acetate, butyl acetate, propylene glycol methyl ether, diethylene glycol methyl ether, methanol, ethanol, isopropanol, and alcohols of higher molecular weight, such as amyl alcohol, tetrahydrofurfuryl alcohol, hexanol, octanol, ethylene glycol, propylene glycol, glycerol, N- methyl-2-pyrrolidone, and the like.

Suitable solid carriers are, for example, talc, titanium dioxide, pyrophyllite clay, silica, attapulgite clay, kieselguhr, limestone, calcium carbonate, bentonite, calcium montmorillonite, cottonseed husks, wheat flour, soybean flour, pumice, wood flour, ground walnut shells, lignin, and similar substances.

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

Further adjuvants that can be used in pesticidal formulations include crystallisation inhibitors, viscosity modifiers, suspending agents, dyes, anti-oxidants, foaming agents, light absorbers, mixing auxiliaries, antifoams, complexing agents, neutralising or pH-modifying substances and buffers, corrosion inhibitors, fragrances, wetting agents, take-up enhancers, micronutrients, plasticisers, glidants, lubricants, dispersants, thickeners, antifreezes, microbicides, and liquid and solid fertilisers. The compositions according to the invention can include an additive comprising an oil of vegetable or animal origin, a mineral oil, alkyl esters of such oils or mixtures of such oils and oil derivatives. The amount of oil additive in the composition according to the invention is generally from 0.01 to 10 %, based on the mixture to be applied. For example, the oil additive can be added to a spray tank in the desired concentration after a spray mixture has been prepared. Preferred oil additives comprise mineral oils or an oil of vegetable origin, e.g., rapeseed oil, olive oil or sunflower oil, emulsified vegetable oil, alkyl esters of oils of vegetable origin, e.g., the methyl derivatives, or an oil of animal origin, such as fish oil or beef tallow. Preferred oil additives comprise alkyl esters of C8-C22 fatty acids, especially the methyl derivatives of C12-C18 fatty acids, e.g., the methyl esters of lauric acid, palmitic acid, and oleic acid (methyl laurate, methyl palmitate and methyl oleate, respectively). Many oil derivatives are known from the Compendium of Herbicide Adjuvants, 10^th Edition, Southern Illinois University, 2010.

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

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

Preferred formulations can have the following compositions (weight %)

Emulsifiable concentrates: active ingredient: 1 to 95 %, preferably 60 to 90 % surface-active agent: 1 to 30 %, preferably 5 to 20 % liquid carrier: 1 to 80 %, preferably 1 to 35 %

Dusts: active ingredient: 0.1 to 10 %, preferably 0.1 to 5 % solid carrier: 99.9 to 90 %, preferably 99.9 to 99 %

Suspension concentrates: active ingredient: 5 to 75 %, preferably 10 to 50 % water: 94 to 24 %, preferably 88 to 30 % surface-active agent: 1 to 40 %, preferably 2 to 30 %

Wettable powders: active ingredient: 0.5 to 90 %, preferably 1 to 80 % surface-active agent: 0.5 to 20 %, preferably 1 to 15 % solid carrier: 5 to 95 %, preferably 15 to 90 %

Granules: active ingredient: 0.1 to 30 %, preferably 0.1 to 15 % solid carrier: 99.5 to 70 %, preferably 97 to 85 %

FORMULATION EXAMPLES

The following Examples further illustrate, but do not limit, the invention.

Wettable powders a) b) c) active ingredients 25 % 50 % 75 % sodium lignosulfonate 5 % 5 % - sodium lauryl sulfate 3 % - 5 % sodium diisobutylnaphthalenesulfonate 6 % 10 % phenol polyethylene glycol ether (7-8 mol of ethylene oxide) 2 % highly dispersed silicic acid 5 % 10 % 10 %

Kaolin 62 % 27 % -

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

Powders for dry seed treatment a) b) c) active ingredients 25 % 50 % 75 % light mineral oil 5 % 5 % 5 % highly dispersed silicic acid 5 % 5 % Kaolin 65 % 40 % -

Talcum 20 %

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

Emulsifiable concentrate active ingredients 10 % octylphenol polyethylene glycol ether (4-5 mol of ethylene oxide) 3 % calcium dodecylbenzenesulfonate 3 % castor oil polyglycol ether (35 mol of ethylene oxide) 4 %

Cyclohexanone 30 % xylene mixture 50 %

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

Dusts a) b) c)

Active ingredients 5 % 6 % 4 %

Talcum 95 %

Kaolin 94 % mineral filler - - 96 %

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

Extruder granules

Active ingredients 15 % sodium lignosulfonate 2 % carboxymethylcellulose 1 %

Kaolin 82 %

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

Coated granules

Active ingredients 8% polyethylene glycol (mol. wt. 200) 3 %

Kaolin 89 %

The finely ground combination is uniformly applied, in a mixer, to the kaolin moistened with polyethylene glycol.

Non-dusty coated granules are obtained in this manner.

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

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

Water 32 %

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

Flowable concentrate for seed treatment active ingredients 40 % propylene glycol 5 % copolymer butanol PO/EO 2 %

Tristyrenephenole with 10-20 moles EO 2 %

1 ,2-benzisothiazolin-3-one (in the form of a 20% solution in water) 0.5 % monoazo-pigment calcium salt 5 %

Silicone oil (in the form of a 75 % emulsion in water) 0.2 % Water 45.3 %

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

Slow-Release Capsule Suspension

28 parts of the combination are mixed with 2 parts of an aromatic solvent and 7 parts of toluene diisocyanate/polymethylene-polyphenylisocyanate-mixture (8:1). This mixture is emulsified in a mixture of 1 .2 parts of polyvinylalcohol, 0.05 parts of a defoamer and 51.6 parts of water until the desired particle size is achieved. To this emulsion a mixture of 2.8 parts 1 ,6-diaminohexane in 5.3 parts of water is added. The mixture is agitated until the polymerization reaction is completed. The obtained capsule suspension is stabilized by adding 0.25 parts of a thickener and 3 parts of a dispersing agent. The capsule suspension formulation contains 28% of the active ingredients. The medium capsule diameter is 8-15 microns. The resulting formulation is applied to seeds as an aqueous suspension in an apparatus suitable for that purpose.

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

EXAMPLES

The following Examples further illustrate, but do not limit, the invention.

ABBREVIATIONS

CDCh Deuterated chloroform

DCM dichloromethane

DMF Dimethylformamide

DMSO Dimethyl sulfoxide

DMSO-d6 Deuterated Dimethyl sulfoxide

EtOAc ethyl acetate eq molecular equivalents

HCI hydrochloric acid h/hrs hour/hours

LC-MS Liquid Chromatography Mass Spectrometry (LCMS or LC-MS) min minutes rt room temperature Rt retention time

TEA triethylamine

THF tetrahydrofuran

TMS tetramethylsilane

PREPARATORY EXAMPLES

Throughout this description, temperatures are given in degrees Celsius (°C) and “mp.” means melting point. LC-MS means Liquid Chromatography Mass Spectrometry and the description of the apparatus, and the methods are as follows. Free radicals represent methyl groups.

¹H NMR and ¹⁹F NMR measurements were recorded on a Bruker 400MHz spectrometer, chemical shifts are given in ppm relevant to a TMS (¹H) or CFCH (¹⁹F) standard. Spectra measured in deuterated solvents as indicated.

Either one of the LC-MS methods was used to characterize the compounds. The characteristic LC-MS values obtained for each compound were the retention time (“Rt”, recorded in minutes) and the measured molecular ion (M+H)⁺.

Method Spectra were recorded on a Mass Spectrometer from Waters Corporation (SQD, SQDII or

QDA Single quadrupole mass spectrometer) equipped with an electrospray source (Polarity: positive and negative ions), Capillary: 0.8-3.00 kV, Cone: 5-30 V, Source Temperature: 120-150°C, Desolvation Temperature: 350-600°C, Cone Gas Flow: 50-150 l/h, Desolvation Gas Flow: 650-1000 l/h, Mass range: 110 to 950 Da and an Acquity UPLC from Waters Corporation: Binary pump, heated column compartment, diodearray detector and ELSD. Column: Waters UPLC HSS T3, 1 .8 pm, 30 x 2.1 mm, Temp: 60°C, DAD Wavelength range (nm): 210 to 400, Runtime: 1 .5 min; Solvents: A = water + 5% MeOH + 0.05 % HCOOH, B= Acetonitrile + 0.05 % HCOOH; Flow (ml/min) 0.85, Gradient: 10% B isocratic for 0.2 min, then 10-100% B in 1 .0 min, 100% B isocratic for 0.2min, 100-10% B in 0.05min, 10% B isocratic for 0.05 min.

LC-MS Method B Spectra were recorded on a ACQUITY Mass Spectrometer from Waters Corporations (SQD or SQDII Single quadrupole mass spectrometer) equipped with an electrospray source (Polarity: positive or negative ions, Capillary: 3.0 kV, Cone: 30V, Extractor: 3.00 V, Source Temperature: 150°C, Desolvation Temperature: 400°C, Cone Gas Flow: 60 L/hr, Desolvation Gas Flow: 700 L/hr, Mass range: 140 to 800 Da) and an ACQUITY UPLC from Waters Corporations with solvent degasser, binary pump, heated column compartment and diode-array detector. Column: Waters UPLC HSS T3, 1.8 pm, 30 x 2.1 mm, Temp: 60°C, DAD Wavelength range (nm): 210 to 400, Solvent Gradient: A = Water/Methanol 9:1 + 0.1 % formic acid, B= Acetonitrile + 0.1 % formic acid, gradient: 0-100% B in 2.5 min; Flow (ml/min) 0.75.

(compound P-1 , Table P)

Step A: Preparation of (2-chloro-5-hvdroxy-phenyl)methylammonium chloride

Borane dimethylsulfide (1.48g, 3.0 eq.) was added to a solution of 2-chloro-5-hydroxybenzonitrile (1.00 g, 1.0 eq.) in THF (18.6 mL) and the resulting reaction mixture was stirred at rt for 1 h and then at 60°C for 2h. The temperature was lowered to rt and an aqueous solution of HCI (4N, 7 mL) was slowly added. The resulting reaction mixture was stirred for 1 h and then concentrated in vacuo. The obtained crude solid material was used in the following step without any further purification.

Step B: Preparation of N-[(2-chloro-5-hvdroxy-phenyl)methyl1propanamide

Diisopropylethylamine (19.5 g, 5.0 eq.), propionic acid (2.7 g, 1.2 eq.) and a solution of propanephosphonic acid anhydride in EtOAc (50% w/w, 29 g, 1.5 eq.) were added to a suspension of (2-chloro-5-hydroxy- phenyl)methylammonium chloride (5.90 g, 1 eq.) in acetonitrile (123 mL) at 5°C. The resulting white suspension was stirred at 5°C for 1 h. Next the crude product was diluted with EtOAc and water. The aqueous phase was extracted with EtOAc; and the combined organic phases were washed with brine and dried over anhydrous sodium sulfate. The resulting crude mixture was concentrated in vacuo and purified by column chromatography on silica gel (eluent: mixtures cyclohexane EtOAc) to afford the desired product.

¹H NMR (400 MHz, CDCb) 6 ppm 7.18 (d, J=8.72 Hz, 1 H) 7.07 (d, J=2.91 Hz, 1 H) 6.74 (dd, J=8.72, 2.91 Hz, 1 H) 6.32 (br s, 1 H) 4.46 (d, J=6.54 Hz, 2 H) 2.20 - 2.31 (m, 2 H) 1 .15 (t, J=7.45 Hz, 3 H)

Step C: Preparation of (2S)-2-(tert-butoxycarbonylamino)propyl methanesulfonate

Methanesulfonyl chloride (7.2g, 62.78 mmol, 1.10 eq) was added dropwise at 0°C to a solution of tert-butyl N- (1 S)-2-hydroxy-1-methyl-ethyl carbamate (10.00 g, 57.07 mmol, 1.00 eq.) and TEA (11.90 mL, 85.61 mmol, 1 .50 eq) in dry THF (200 mL). The resulting reaction mixture was left to stir at rt for 2 h. The reaction mixture was diluted with water and extracted with EtOAc. The organic layers were combined and dried over anhydrous sodium sulphate, filtered, and concentrated in vacuo to obtain the title compound.

¹H NMR (400 MHz, CDCb) 6 ppm 1 .24 (d, J=7.00 Hz, 3 H) 1 .45 (s, 9 H) 3.04 (s, 3 H) 3.98 (m, 1 H) 4.12 - 4.24 (m, 2 H).

Step D: Preparation of tert-butyl N-[(1 S)-2-[4-chloro-3-[(propanoylamino)methyl1phenoxy1-1-methyl- ethyll carbamate

Cesium carbonate (6.6g, 20 mmol, 3.0 eq.) and (2S)-2-(tert-butoxycarbonylamino)propyl methanesulfonate (2.31g, 8.67 mmol, 1 .3 eq.) were added to a solution of N-[(2-chloro-5-hydroxy-phenyl)methyl]propenamide (1 .5 g, 6.7 mmol) in acetonitrile (37.9 mL), and the reaction mixture was stirred at 70°C for 24 h. The reaction mixture was diluted with EtOAc and water, and the aqueous phase extracted with EtOAc. The combined organic phases were washed with brine, dried over anhydrous sodium sulfate, and concentrated in vacuo. Purification by column chromatography on silica gel (eluent: mixtures cyclohexane EtOAc) to afford the desired product.

¹H NMR (400 MHz, CDCb) 6 ppm 7.24 (d, J=8.72 Hz, 1 H) 6.94 (d, J=2.91 Hz, 1 H) 6.76 (dd, J=8.72, 2.91 Hz, 1 H) 5.93 (br s, 1 H) 4.73 (br s, 1 H) 4.48 (d, J=5.81 Hz, 2 H) 4.02 (br s, 1 H) 3.84 - 3.93 (m, 2 H) 2.25 (q, J=7.51 Hz, 2 H) 1 .44 (s, 9 H) 1 .24 - 1 .28 (d, 3 H) 1 .17 (t, J=7.63 Hz, 3 H).

Step E: Preparation of tert-butyl N-[(1 S)-2-[4-cvano-3-[(propanoylamino)methyl1phenoxy1-1-methyl- ethyll carbamate

Zinc cyanide (60 mg, 1.0 eq.), 2-Dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl (121 mMg, 0.5 eq.) and allylpalladium(ll)-chlorid-dimer (93 mg, 0.5 eq.) were added to a solution of N-[(1 S)-2-[4-chloro-3- [(propanoylamino)methyl]phenoxy]-1-methyl-ethyl]carbamate (0.19 g, 0.51 mmol, 1.0 eq.) in DMF (2.56 mL) and the resulting reaction mixture was heated for 3 h at 110°C. The reaction mixture was cooled to rt and diluted with EtOAc and water. The aqueous phase was extracted with EtOAc, and the combined organic layers were washed with a saturated aqueous solution of sodium bicarbonate and brine. After drying over anhydrous sodium sulfate and concentration in vacuo, the desired compound was purified by column chromatography on silica gel (eluent: mixtures cyclohexane/EtOAc).

¹H NMR (400 MHz, CDCb) 6 = 7.58 (d, J = 8.7 Hz, 1 H), 7.07 (d, J = 1.8 Hz, 1 H), 6.93 - 6.84 (m, 1 H), 6.26 - 5.98 (m, 1 H), 4.77 - 4.63 (m, 1 H), 4.59 (d, J = 6.2 Hz, 2H), 4.15 - 3.94 (m, 3H), 2.36 - 2.23 (m, 2H), 1.47 (s, 9H), 1 .35 - 1 .26 (m, 3H), 1 .20 (t, J = 7.4 Hz, 3H) Step F: Preparation of [(1 S)-2-[4-cvano-3-[(propanoylamino)methyl1phenoxy1-1-methyl-ethyl1ammonium chloride

A 37% aqueous solution of hydrochloric acid (2.7g, 5.0 eq.) was added to a solution of N-[(1 S)-2-[4-cyano-3- [(propanoylamino)methyl]phenoxy]-1-methyl-ethyl]carbamate (80 mg, 0.2 mmol, 1 .0 eq.) in EtOAc (1.0 mL). The resulting reaction mixture was stirred for 2h at rt. The organic solvent was evaporated under reduced pressure and the crude product obtained as a white solid was used in the following reaction without further purification.

Step G: N-[(1 S)-2-(2,4-difluoro-5-methyl-phenoxy)-1-methyl-ethyl1-1 ,1 ,1-trifluoro-methanesulfonamide

TEA (50 mg, 3.5 eq.) and trifluoromethanesulfonic anhydride (40 mg, 1.0 eq.) were added to a suspension of [(1 S)-2-[4-cyano-3-[(propanoylamino)methyl]phenoxy]-1-methyl-ethyl]ammonium chloride (50 mg, 0.14 mmol) acetonitrile (0.7 mL) at -40°C. The resulting pale solution was stirred at -40°C for 40 min and then quenched with water. The reaction mixture was extracted with EtOAc, and the combined organic layers were washed with brine and dried over anhydrous sodium sulfate. Concentration in vacuo and purification by column chromatography on silica gel (eluent: mixtures cyclohexane/EtOAc) afforded the desired product.

¹H NMR (400 MHz, CDCb) 6 7.62-7.58 (d, 1 H) 7.08 (s, 1 H) 6.90-6.85 (d, 1 H) 6.45-6.35 (m, 1 H) 4.60-4.40 (m, 2H) 4.20-3.90 (m, 3H), 2.28 (q, 2H), 1.42 (d, 3H), 1.15 (t, 3H). ¹⁹F NMR (377 MHz, CDCb) 6 ppm -77.77 (s, 3 F).

Example P2: Preparation of N-[[2-cvano-5-[(2S)-2-(difluoromefhylsulfonylamino)propoxy1phenyl1mefhyl1- propanamide (compound P-2, Table P)

Under Argon [(1 S)-2-[4-cyano-3-[(propanoylamino)methyl]phenoxy]-1-methyl-ethyl]ammonium chloride (130 mg, 0.39 mmol, 1 eq.; preparation described in preparative example 1 , Step A-F) was suspended in DCM (2.6 mL) and 1 -methylimidazole (130 mg, 1.57 mmol, 4 eq.) was added. The reaction mixture was cooled down to 0°C and difluoromethanesulfonyl chloride (80 mg, 0.51 mmol, 1.3 eq.) was added slowly. The reaction mixture was stirred for 10 min at 0 C before it was diluted with DCM and saturated aqueous NaHCOs solution. The phases were separated, and the organic phase was dried using magnesium sulfate, filtered, and concentrated under reduced pressure. Purification via column chromatography on silica gel using a gradient of cyclohexane and EtOAc as the mobile phase afforded the desired product.

¹H NMR (400 MHz, CDCb) 5 = 7.67 - 7.52 (m, 1 H), 7.09 (s, 1 H), 6.88 (br d, J = 8.7 Hz, 1 H), 6.39 - 6.05 (m, 2H), 5.12 (br d, J = 7.6 Hz, 1 H), 4.58 (br d, J = 6.5 Hz, 2H), 4.18 - 4.01 (m, 3H), 2.39 - 2.24 (m, 2H), 1 .50 - 1 .42 (m, 3H), 1 .24 - 1 .1 1 (m, 3H). ¹⁹F NMR (376 MHz, CDCb) 5 = -121 .99 (br d, J = 26.8 Hz, 2F)

Example P3: Preparation of N-[[2-cvano-5-[(2S)-2-(difluoromethylsulfonylamino)propoxy1-4-fluoro-

P-3, Table

In a round bottom flask 2-bromo-4-fluoro-5-methoxybenzonitrile (2 g, 8.4 mmol, 1 eq.) was dissolved in THF and borane-dimethyl sulfide complex (1 .6g, 21 mmol, 2.5 eq.), CAS: 13292-87-0) was added dropwise. The resulting colorless solution was vigorously stirred at 60°C for 3 hr, upon which a white suspension formed. After cooling the reaction mixture to 0°C 4 M HCI (7.4 mL, 29.5 mmol, 3.5 eq.) was added and the resulting reaction mixture was stirred for further 30 min, diluted with EtOAc, and the layers were separated. The aqueous layer was washed with 4 M HCI. The combined aqueous layers were basified using 8 M aqueous NaOH solution to pH 8. The aqueous layer was extracted with EtOAc, and the combined organic layers were dried using sodium sulfate, filtered, and concentrated under reduced pressure to yield the desired product as a light-yellow gum. The crude mixture (approximate 90% purity) was used directly for the next step without any further purification.

¹H NMR (400 MHz, CDCb) 6 = 7.31 - 121 (m, 1 H), 7.08 (d, J = 9.1 Hz, 1 H), 3.92 (s, 3H), 3.89 (s, 2H); ¹⁹F NMR (377 MHz, CDCb) 5 = -135.35 (s, 1 F)

Step B: Preparation of N-[(2-bromo-4-fluoro-5-methoxy-phenyl)methyl1propanamide

A flask was charged with (2-bromo-4-fluoro-5-methoxy-phenyl)methanamine (0.86g, 3.66 mmol, 1 eq.) and

EtOAc (29 mL). The reaction mixture was cooled down to 0°C and 2 M aqueous NaOH solution was added (29 mL), and afterwards propionyl chloride (0.39 g, 4 mmol, 1.1 eq.) was added dropwise. After stirring for 30 min at 0°C, the reaction mixture was diluted with water and extracted with EtOAc. The combined organic phases were dried over Na2SO4, filtered, and concentrated under reduced pressure. Purification via column chromatography on silica gel ( cyclohexane and EtOAc as the mobile phase) afforded the desired product.

¹H NMR (400 MHz, CDCb) 6 = 7.31 - 7.26 (m, 1 H), 7.08 (d, J = 8.7 Hz, 1 H), 6.03 - 5.85 (m, 1 H), 4.47 (d, J = 6.2 Hz, 2H), 3.96 - 3.83 (m, 3H), 2.26 (q, J = 7.6 Hz, 2H), 1.19 (t, J = 7.6 Hz, 3H). ¹⁹F NMR (377 MHz, CDCb) 5 = -133.72 (s, 1 F)

Step C: Preparation of N-[(2-bromo-4-fluoro-5-hvdroxy-phenyl)methyl1propenamide

Under argon N-[(2-bromo-4-fluoro-5-methoxy-phenyl)methyl]propenamide (0.89 g, 3.1 mmol, 1 eq.) was dissolved in DCM (7.7 mL), cooled down to 0°C, and a 1 M solution of boron tribromide in DCM (6.1 mL, 6.1 mmol, 2 eq.) was added dropwise. After the addition was complete the cold bath was removed, and the reaction mixture was allowed to stir at rt for 90 min. The reaction mixture was cooled down to 0°C before a saturated aqueous NaHCOs solution was slowly added. The mixture was extracted with EtOAc, and the combined organic layers were dried over sodium sulfate, filtered, and concentrated in vacuo. The crude material was directly used for the next step without any further purification.

¹H NMR (400 MHz, CDCb) 6 = 7.32 - 7.23 (m, 2H), 6.34 - 6.12 (m, 1 H), 4.47 (d, J = 6.2 Hz, 2H), 2.31 (q, J = 7.4 Hz, 2H), 1.20 (t, J = 7.6 Hz, 3H). ¹⁹F NMR (377 MHz, CDCb) 6 = -132.07 to - 144.14 (m, 1 F)

Step D: Preparation of tert-butyl N-[(S)-2-[4-bromo-2-fluoro-5-[(propanoylamino)methyl1phenoxy1-1 -methyl- ethyll carbamate

In a flask N-[(2-bromo-4-fluoro-5-hydroxy-phenyl)methyl]propenamide (160 mg, 0.58 mmol, 1 eq.) was dissolved in DMF (2.3 mL), and cesium carbonate (380 mg, 1 .16 mmol, 2 eq.) was added, followed by the addition of (2S)-2-(tert-butoxycarbonylamino)propyl methanesulfonate (0.21 g, 0.81 mmol, 1.4 eq. (preparation is described in preparative example 1 , step C). The reaction mixture was stirred at 60°C for 6 hrs. After the reaction mixture was allowed to reach rt, water was added, and the mixture was extracted with EtOAc. The combined organic layers were dried over sodium sulfate, filtered, and concentrated under reduced pressure. Purification via column chromatography on silica gel using a gradient of cyclohexane and EtOAc as the mobile phase afforded the desired product. ¹H NMR (400 MHz, CDCb) 6 = 7.29 (br d, J = 10.2 Hz, 1 H), 7.10 (d, J = 8.4 Hz, 1 H), 5.97 (br s, 1 H), 4.87 - 4.67 (m, 1 H), 4.46 (d, J = 6.2 Hz, 2H), 4.13 - 3.92 (m, 3H), 2.28 (q, J = 7.6 Hz, 2H), 1 .47 (s, 9H), 1 .31 (d, J = 6.5 Hz, 3H), 1 .19 (t, J = 7.6 Hz, 3H). ¹⁹F NMR (377 MHz, CDCb) 6 = -133.02 (br s, 1 F)

Step F: Preparation of tert-butyl N-[(1 S)-2-[4-cvano-2-fluoro-5-[(propanoylamino)methyl1phenoxy1-1-methyl- ethyll carbamate

In a vial tert-butyl N-[(S)-2-[4-bromo-2-fluoro-5-[(propanoylamino)methyl]phenoxy]-1-methyl-ethyl]carbamate (0.18g, 0.42 mmol, 1 eq.) was dissolved in DMF (2.1 mL). The solution was degassed using a stream of argon, then zinc cyanide (50 mg, 0.42 mmol, 1 eq.), X-Phos (CAS: 564483-18-7; 100 mg, 0.21 mmol, 0.5 eq) and [Pd(allyl)CI]2 (CAS: 12012-95-2; 78 mg, 0.21 mmol, 0.5 eq.) were added. The vial was sealed, and the resulting suspension was stirred at 105°C for 45 min. The reaction mixture was allowed to reach rt, saturated NaHCOs solution was added, and extracted with EtOAc. The combined organic layers were dried using sodium sulfate, filtered, and concentrated under reduced pressure. Purification via column chromatography on silica gel using a gradient of cyclohexane and EtOAc as the mobile phase afforded the desired product.

¹H NMR (400 MHz, CDCb) 6 = 7.34 (d, J = 10.2 Hz, 1 H), 7.20 (d, J = 8.0 Hz, 1 H), 6.16 - 6.08 (m, 1 H), 4.78 - 4.65 (m, 1 H), 4.55 (d, J = 6.5 Hz, 2H), 4.18 - 4.01 (m, 3H), 2.29 (q, J = 7.6 Hz, 2H), 1 .47 (s, 9H), 1.36 - 1.29 (m, 3H), 1.19 (t, J = 7.4 Hz, 3H). ¹⁹F NMR (377 MHz, CDCb) 6 = -133.43 (s, 1 F)

Step G: Preparation of [(S)-2-[4-cvano-2-fluoro-5-[(propanoylamino)methyl1phenoxy1-1-methyl-ethyl1- ammonium chloride

In a vial tert-butyl N-[(1 S)-2-[4-cyano-2-fluoro-5-[(propanoylamino)methyl]phenoxy]-1-methyl-ethyl]carbamate (87 mg, 0.23 mmol, 1 eq.) was dissolved in EtOAc, cooled down to 0°C before 32% aqueous HCI solution was added dropwise (0.1 1 mL, 1 .1 mmol, 5 eq.). After the addition was complete, the reaction mixture was allowed to reach rt, and stirred for 3.5 hrs at rt. The reaction mixture was partially concentrated under reduced pressure, followed by trituration with DCM which caused a solid to form. The supernatant was removed and the solid was fully dried under reduced pressure to afford the desired product, which was used for the next step without any further purification or characterization.

Step H: Preparation of N-[[2-cvano-5-[ -2-(difluoromethylsulfonylamino)propoxy1-4-fluoro-phenyl1- methyllpropenamide

In a vial and under argon, [(S)-2-[4-cyano-2-fluoro-5-[(propanoylamino)methyl]phenoxy]-1-methyl- ethyl]ammonium chloride (72 mg, 0.3 mmol, 1 eq.) was suspended in DCM (2.3 mL), cooling to rt, and 1 - methylimidazole (110 mg, 1.4 mmol, 6 eq.) was added followed by drop-wise addition of 1 ,1 - difluoromethanesulfonyl chloride (40 mg, 0.25 mmol, 1.1 eq.). After stirring at 0°C for 15 min, saturated aqueous NaHCOs solution was added, and the mixture was extracted with DCM. The combined organic phase was washed with brine, dried over sodium sulfate, filtered, and concentrated under reduced pressure. Purification via column chromatography on silica gel using a gradient of cyclohexane and EtOAc as the mobile phase afforded the desired product.

¹H NMR (400 MHz, CDCb) 6 = 7.36 (d, J = 10.2 Hz, 1 H), 7.23 - 7.18 (m, 1 H), 6.42 - 6.05 (m, 2H), 5.30 (br d, J = 8.7 Hz, 1 H), 4.53 (d, J = 6.2 Hz, 2H), 4.26 - 4.04 (m, 3H), 2.28 (q, J = 7.4 Hz, 2H), 1.48 (d, J = 6.9 Hz, 3H), 1.18 (t, J = 7.6 Hz, 3H). ¹⁹F NMR (377 MHz, CDCb) 6 = -122.19 (d, J = 79.6 Hz, 2F), -132.45 to -133.66 (m, 1 F) methyllpropenamide (compound P-4, Table P)

(compound P-4, Table P)

Step A: Preparation of tert-butyl A/-[(1 S)-2-(4-cvano-2-fluoro-5-methyl-phenoxy)-1-methyl-ethyl1carbamate

To a solution of 5-Fluoro-4-hydroxy-2-methylbenzonitrile (2.00 g, 12.6 mmol) in THF (63 mL) were added N- Boc-L-alaninol (2.50 g, 13.8 mmol) and triphenylphosphine (3.66 g, 13.8 mmol) then diisopropyl azodicarboxylate (2.94 g, 13.8 mmol) was added dropwise and the resulting reaction mixture was stirred for 2 hours at rt. Then, water was added, and the mixture was extracted with EtOAc. The combined organic layers were washed with saturated aqueous sodium bicarbonate solution, dried over magnesium sulfate, filtered and the solvent was removed under reduced pressure. Purification by column chromatography afforded tert-butyl A/-[(1 S)-2-(4-cyano-2-fluoro-5-methyl-phenoxy)-1-methyl-ethyl] carbamate.

¹H NMR (CDCb) 6: 7.30-7.34 (d, 1 H), 6.83-6.95 (d, 1 H), 4.67-4.81 (br s, 1 H), 3.99-4.19 (m, 3H), 2.46-2.59 (s, 3H), 1.46-1.49 (s, 9H), 1.29-1.36 (d, 3H). ¹⁹F NMR (CDCb) 6: -136.21 (m, 1 F) Step B: Preparation of [(1 S)-2-(4-cvano-2-fluoro-5-methyl-phenoxy)-1-methyl-ethyl1ammonium chloride te/Y-butyl A/-[(1 S)-2-(4-cyano-2-fluoro-5-methyl-phenoxy)-1-methyl-ethyl]carbamate (2.7g, 8.7 mmol) was dissolved in EtOAc (44 mL) and the reaction mixture was cooled down to 0°C. Then 5 mL of a 37% aqueous HCI solution was added slowly and, after the addition was complete, the reaction mixture was allowed to stir at rt for 5 hours. The solvents were removed under reduced pressure and the residue was resuspended in 10 mL of diisopropyl ether followed by stirring. The solid was filtered and the filter cake was washed with additional diisopropyl ether followed by pentane to afford [(1 S)-2-(4-cyano-2-fluoro-5-methyl-phenoxy)-1-methyl- ethyl]ammonium chloride.

¹H NMR (400 MHz, DMSO-d6) 6 ppm 8.34 (br s, 3 H) 7.79 (d, J=11 .26 Hz, 1 H) 7.37 (d, J=8.36 Hz, 1 H) 4.19 - 4.32 (m, 2 H) 3.58 - 3.68 (m, 1 H) 2.46 (s, 3 H) 1.30 (d, J=6.54 Hz, 3 H). ¹⁹F NMR (377 MHz, DMSO-d6) 5 ppm -135.88 (s, 1 F)

Step C: Preparation of A/-[(1 S)-2-(4-cvano-2-fluoro-5-methyl-phenoxy)-1-methyl-ethyl1-1 , 1 ,1 -trifluoro- methanesulfonamide

[(1 S)-2-(4-cyano-2-fluoro-5-methyl-phenoxy)-1-methyl-ethyl]ammonium chloride (1.8 g, 7.4 mmol) was suspended in acetonitrile (37 mL) and the reaction mixture was cooled down to -40°C. Triethylamine (1.9 g, 18.5 mmol) was added, followed by the drop-wise addition of trifluoromethanesulfonic anhydride (2.2g, 7.8 mmol). Stirring was continued at -40°C for 30 minutes before water and EtOAc were added. After the reaction mixture was allowed to reach rt it was extracted between EtOAc and saturated NaHCOs solution. The combined organic layers were dried over sodium sulfate, filtered and the solvent was removed under reduced pressure. The residue was purified via column chromatography to afford N-[(1 S)-2-(4-cyano-2-fluoro-5-methyl-phenoxy)- 1-methyl-ethyl]-1 ,1 ,1-trifluoro-methanesulfonamide.

¹H NMR (400 MHz, CDCb) 6 ppm 7.33 (d, J=10.54 Hz, 1 H) 6.85 (d, J=7.99 Hz, 1 H) 5.32 (br d, J=7.99 Hz, 1 H) 4.03 - 4.22 (m, 4 H) 2.52 (s, 3 H) 1 .50 (d, J=6.90 Hz, 3 H). ¹⁹F NMR (377 MHz, CDCb) 6 ppm -77.80 (s, 3

F) -135.74 (s, 1 F) i-4-cyano-2-fluoro-phenoxy]-1-methyl-ethyl]-1 ,1 , 1 -trifluoro-

N-[(1 S)-2-(4-cyano-2-fluoro-5-methyl-phenoxy)-1-methyl-ethyl]-1 ,1 ,1-trifluoro-methanesulfonamide (2.3 g 6.7 mmol) was suspended in 1 ,1 ,1 -trifluorotoluene (9.2 mL). After the reaction mixture was degassed via a flow of argon, N-bromosuccinimide (1.32 g. 7.36 mmol) was added, followed by the addition of azobisisobutyronitrile (56 mg, 0.34 mmol). The reaction mixture was heated to 80°C for 4 hours and was allowed to reach rt. A further 360 mg of N-bromo succinimide (2 mmol) was added and stirring at 80°C was continued for 2 hours. The reaction mixture was allowed to reach rt before water and EtOAc was added. The mixture was extracted EtOAc and the combined organic layers were dried over sodium sulfate, filtered and concentrated under reduced pressure. Purification via column chromatography afforded A/-[(1 S)-2-[5-(bromomethyl)-4-cyano-2-fluoro- phenoxy]-1-methyl-ethyl]-1 ,1 ,1-trifluoro-methanesulfonamide.

1 H NMR (400 MHz, CDCb) 6 ppm 7.40 (d, J=10.17 Hz, 1 H) 7.10 (d, J=7.63 Hz, 1 H) 5.26 (br d, J=8.36 Hz, 1 H) 4.59 (s, 2 H) 4.19 - 4.24 (m, 1 H) 4.10 - 4.14 (m, 2 H) 1.51 (d, J=6.54 Hz, 3 H) 19F NMR (377 MHz, CDCb) 6 ppm -77.76 (s, 3 F) -130.65 (s, 1 F) i-4-cyano-2-fluoro-phenoxyl-1-methyl-ethyll-1 ,1 , 1 -trifluoro- methanesulfonamide

A/-[(1 S)-2-[5-(bromomethyl)-4-cyano-2-fluoro-phenoxy]-1-methyl-ethyl]-1 ,1 ,1-trifluoro-methanesulfonamide (700 mg, 1 .7 mmol) was dissolved in acetonitrile (8.3 mL) and the reaction mixture was heated 80°C for 90 minutes. The reaction mixture was allowed to reach rt and saturated NaHCOs solution was added. The reaction mixture was extracted with EtOAc, and the combined organic layers were dried over sodium sulfate, filtered and concentrated under reduced pressure to afford A/-[(1 S)-2-[5-(azidomethyl)-4-cyano-2-fluoro-phenoxy]-1- methyl-ethyl]-1 ,1 ,1-trifluoro-methanesulfonamide.

¹H NMR (400 MHz, CDCb) 6 ppm 7.43 (d, J=10.17 Hz, 1 H) 7.08 (d, J=7.63 Hz, 1 H) 5.26 (br d, J=8.36 Hz, 1 H) 4.61 (s, 2 H) 4.21 - 4.26 (m, 1 H) 4.10 - 4.15 (m, 2 H) 1.51 (d, J=6.54 Hz, 3 H) ¹⁹F NMR (377 MHz, CDCb)

5 ppm -77.77 (s, 3 F) -131 .61 (s, 1 F)

A/-[(1 S)-2-[5-(azidomethyl)-4-cyano-2-fluoro-phenoxy]-1-methyl-ethyl]-1 ,1 ,1-trifluoro-methanesulfonamide (100 mg, 0.26 mmol), 1 ,2-Di(pyridin-2-yl)diselane (CAS: 59957-75-4, 17 mg, 0.05 mmol) and propionic acid (20 mg, 0.26 mmol) were dissolved in toluene (2 mL). The reaction mixture was cooled down to 0°C before trimethyl phosphine (1 M solution in toluene, 0.63 mmol, 0.63 mL) was added drop wise and stirring was continued for 2 hours. The reaction mixture was stirred for an additional 1 h at rt before it was diluted with EtOAc. This reaction mixture was extracted with saturated NaHCOs solution followed by washing with 0.5 M aqueous HCI. The organic layer was then dried using sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified via column chromatography to afford N-[[2-cyano-4-fluoro-5-[(2S)-2- (trifluoromethylsulfonylamino)propoxy]phenyl]methyl]propenamide.

¹H NMR (400 MHz, CDCb) 6 ppm 7.32 (d, J=10.17 Hz, 1 H) 7.20 (d, J=7.99 Hz, 1 H) 6.27 (br t, J=5.63 Hz, 1 H) 6.10 (br d, J=8.72 Hz, 1 H) 4.45 - 4.56 (m, 2 H) 4.15 - 4.21 (m, 1 H) 4.07 - 4.13 (m, 2 H) 2.27 (q, J=7.63 Hz, 2 H) 1 .46 (d, J=6.54 Hz, 3 H) 1 .16 (t, J=7.45 Hz, 3 H). ¹⁹F NMR (377 MHz, CDCb) 6 ppm -77.87 (s, 3 F) -132.83 (s, 1 F)

Example P5: Preparation of N-[[4-fluoro-5-[(2S)-2-[methoxymethyl(trifluoromethylsulfonyl)amino]propoxy]-2- methyl-phenyl]methyl]propenamide (compound P-18, Table P)

(compound P-18, Table P)

To a reaction vessel was added A/-[[4-fluoro-2-methyl-5-[(2S)-2-

(trifluoromethylsulfonylamino)propoxy]phenyl]methyl]propenamide (preparation described in example P4; 31 mg, 0.076 mmol, 1 .0 eq.) at room temperature. Acetonitrile (0.46 mL) was added, followed by triethylamine (32 pL, 0.23 mmol, 3.0 eq.). Chloromethyl methyl ether (6.6 pL, 0.11 mmol, 1 .5 eq.) was then added dropwise over 1 hour. Subsequently, a second portion of chloromethyl methyl ether (6.6 pL, 0.11 mmol, 1.5 eq.) was added and the mixture was stirred for 45 minutes. The reaction was quenched with water and extracted with ethyl acetate. The organic phase was washed with brine, dried, filtered, and concentrated under reduced pressure. The resulting residue was purified by column chromatography to yield the desired product.

¹H NMR (400 MHz, CDCb) 6 ppm 7.34 (d, J=9.81 Hz, 1 H) 7.16 (d, J=7.63 Hz, 1 H) 6.19 (br s, 1 H) 4.84 (s, 2 H) 4.54 (d, J=6.18 Hz, 2 H) 4.38 - 4.49 (m, 1 H) 4.24 - 4.32 (m, 1 H) 4.12 - 4.19 (m, 1 H) 3.38 (s, 3 H) 2.27 (q, J=7.63 Hz, 2 H) 1 .48 (d, J=6.90 Hz, 3 H) 1 .17 (t, J=7.45 Hz, 3 H). ¹⁹F NMR (377 MHz, CDCb) 6 ppm -76.92 (br s, 3 F) -132.85 (br s, 1 F)

Examples of synthesized compounds of formula (I) are shown in Table P. 114

Table P: Synthesized compounds and Spectral and Physical Chemical Data. 115 116

BIOLOGICAL EXAMPLES

Example B1 : Euschistus heros (Neotropical Brown Stink Bug) Soybean leaves on agar in 24-well microtiter plates were sprayed with aqueous test solutions prepared from 10'000 ppm DMSO stock solutions. After drying the leaves were infested with N2 nymphs. The samples were assessed for mortality and growth inhibition in comparison to untreated samples 5 days after infestation. The following compounds gave an effect of at least 80% in at least one of the two categories (mortality or growth inhibition) at an application rate of 200 ppm: P-1 , P-4, P-16 Example B2: Myzus persicae (Green peach aphid) Systemic activity

Roots of pea seedlings infested with an aphid population of mixed ages were placed directly into aqueous test solutions prepared from 10'000 DMSO stock solutions. The samples were assessed for mortality 6 days after placing seedlings into test solutions. The following compounds resulted in at least 80% mortality at a test rate of 24 ppm: P-1 , P-4, P-7, P-13 Example B3: Myzus persicae (Green peach aphid) Intrinsic activity

Test compounds prepared from 10'000 ppm DMSO stock solutions were applied by pipette into 24-well microtiter plates and mixed with nutrient solution. The plates were closed with a stretched Parafilm. A plastic stencil with 24 holes was placed onto the plate and infested pea seedlings were placed directly on the Parafilm. The infested plate was closed with a gel blotting paper and another plastic stencil and then turned upside down. The samples were assessed for mortality 5 days after infestation. The following compounds resulted in at least 80% mortality at a test rate of 12 ppm: P-1 , P-3, P-4, P-5, P-6, P-7, P-8, P-9, P-10, P-11 , P-12, P-13, P-15, P- 16, P-17, P-18, P-19

Eggplant leaf discs were placed onto agar in a 24-well microtiter plate and sprayed with aqueous test solutions prepared from 10'000 ppm DMSO stock solutions. After drying, the leaf discs were infested with an aphid population of mixed ages. The samples were assessed for mortality 6 days after infestation. The following compounds resulted in at least 80% growth inhibition at an application rate of 200 ppm: P-1 , P-3, P-4, P-6, P- 7, P-10, P-12, P-13, P-16, P-17, P-18

Example B5: Plutella xylostella (Diamond back moth)

24-well microtiter plates with artificial diet were treated with aqueous test solutions prepared from 10'000 ppm DMSO stock solutions by pipetting. After drying, Plutella eggs were pipetted through a plastic stencil onto a gel blotting paper and the plate was closed with it. The samples were assessed for mortality and growth inhibition in comparison to untreated samples 8 days after infestation. The following compounds gave an effect of at least 80% in at least one of the two categories (mortality or growth inhibition) at an application rate of 200 ppm: P-1 , P-4, P-5, P-6, P-7, P-8, P-1 1 , P-12, P-13, P-14, P-18, P-19

Bean leaf discs on agar in 24-well microtiter plates were sprayed with aqueous test solutions prepared from 10'000 ppm DMSO stock solutions. After drying the leaf discs were infested with a mite population of mixed ages. The samples were assessed for mortality on mixed population (mobile stages) 6 days after infestation. The following compounds resulted in at least 80% mortality at an application rate of 200 ppm: P-1 , P-4, P-7, P- 12, P-17, P-18 root

Maize sprouts placed onto an agar layer in 24-well microtiter plates were treated with aqueous test solutions prepared from 10'000 ppm DMSO stock solutions by spraying. After drying, the plates were infested with L2 larvae (6 to 10 per well). The samples were assessed for mortality and growth inhibition in comparison to untreated samples 4 days after infestation. The following compounds gave an effect of at least 80% in at least one of the two categories (mortality or growth inhibition) at an application rate of 200 ppm: P-4, P17, P-18 flower

Bean leaf discs were placed on agar in 24-well microtiter plates and sprayed with aqueous test solutions prepared from 10'000 DMSO stock solutions. After drying the leaf discs were infested with a Frankliniella population of mixed ages. The samples were assessed for mortality 4 days after infestation. The following compounds resulted in at least 80% growth inhibition at an application rate of 200 ppm: P-4, P-7, P-10, P-13, P-18 Example B9: Bemisia tabaci (Cotton white fly) Feeding/contact activity

Cotton leaf discs were placed on agar in 24-well microtiter plates and sprayed with aqueous test solutions prepared from 10'000 ppm DMSO stock solutions. After drying the leaf discs were infested with adult white flies. The samples were checked for mortality 6 days after incubation. The following compounds resulted in at least 80% mortality at an application rate of 200 ppm: P-18

Example B10: Spodoptera littoralis (Egyptian cotton leaf worm)

Cotton leaf discs were placed onto agar in 24-well microtiter plates and sprayed with aqueous test solutions prepared from 10'000 ppm DMSO stock solutions. After drying the leaf discs were infested with five L1 larvae. The samples were assessed for mortality, anti-feeding effect, and growth inhibition in comparison to untreated samples 3 days after infestation. Control of Spodoptera littoralis by a test sample is given when at least one of the categories mortality, anti-feedant effect, and growth inhibition is higher than the untreated sample. The following compounds resulted in at least 80% control at an application rate of 200 ppm: P-18

Claims

1. A compound of the formula (I) wherein

R¹ is selected from hydrogen, Ci-C4-alkyl, Ci-C4-haloalkyl, Cs-Ce-cycloalkyl, Cs-Ce-halocycloalkyl, cyano-Ci-C4-alkyl, C3-C6-cycloalkyl-Ci-C4-alkyl, cyano-Cs-Ce-cycloalkyl, Ci-C4-alkoxy, C1-C4- haloalkoxy, C2-C4-alkynyloxy, Ci-C4-alkoxy-Ci-C4-alkyl, Ci-C4-alkoxy-Ci-C4-alkoxy, Cs-Ce-cycloalkyl- Ci-C4-alkoxy, Cs-Ce-cycloalkyloxy, N-(Ci-C4-alkyl)amino, N-(C3-C6-cycloalkyl)amino, N,N-di(Ci-C4- alkyl)amino, Ci-C4-alkoxyamino-Ci-C4-alkyl, Ci-C4-alkoxyimino, Ci-C4-alkylsulfonyl-Ci-C4-alkyl, C1-C4- alkylsulfanyl-Ci-C4-alkyl, Ci-C4-alkoxycarbonyl-Ci-C4-alkyl, Ci-C4-alkylcarbonyloxy-Ci-C4-alkyl, C1-C4- alkylcarbonylamino-Ci-C4-alkyl, Ci-C4-alkoxycarbonylamino-Ci-C4-alkyl, phenoxy-Ci-C4-alkyl, phenoxy, Cs-Cs-bicycloalkyl, 3-, 4-, 5- or 6-membered heterocycloalkyl, phenyl, phenyl-Ci-C4-alkyl, 5- or 6-membered heteroaryl, or 5- or 6-membered heteroaryl-Ci-Cs-alkyl; wherein any of said 3-, 4-, 5- or 6-membered heterocycloalkyl contains 1 or 2 heteroatoms or groups individually selected from N, O, S, S=O, or SO2, with the proviso that no more than one is O, S, S=O or SO2; wherein any of said 5- or 6-membered heteroaryl and heteroaryl-Ci-Cs-alkyl contains 1 , 2, 3 or 4 heteroatoms individually selected from N, S, or O, with the proviso that no more than one is O or S; wherein any of said C3-C6- cycloalkyl, and 3-, 4-, 5- or 6-membered heterocycloalkyl are unsubstituted or substituted by 1 , 2 or 3 substituents independently selected from halogen, cyano, Ci-Cs-alkyl, Ci-Cs-haloalkyl, or C3-C6- cycloalkyl; and wherein any of said phenyl, said 5- or 6-membered heteroaryl and heteroaryl-Ci-Cs- alkyl are unsubstituted or substituted by 1 , 2 or 3 substituents independently selected from halogen, cyano, Ci-C4-alkyl, Ci-C4-haloalkyl, or Ci-C4-alkoxy;

R² is selected from hydrogen, Ci-C4-alkyl, Ci-C4-alkoxy, Ci-C4-alkoxy-Ci-C4-alkyl, cyano-Ci-C4-alkyl, Ci-C4-alkylcarbonyl or Ci-C4-alkoxycarbonyl;

R³ is selected from hydrogen, or Ci-Cs-alkyl;

R⁴ is selected from hydrogen, halogen, or Ci-Cs-alkyl;

R⁵ and R⁶ are independently selected from hydrogen, or Ci-Cs-alkyl; or R⁵ and R⁶ together with the carbon to which they are attached represent a Cs-Cs-cycloalkyl group;

R⁷ is selected from Ci-C4-alkyl, Ci-C4-haloalkyl, Cs-Ce-cycloalkyl, phenyl, or 5- or 6-membered heteroaryl; wherein any of said Cs-Ce-cycloalkyl is unsubstituted or substituted by 1 , 2 or 3 substituents independently selected from halogen, cyano, Ci-Cs-alkyl, or Ci-Cs-haloalkyl; wherein any of said 5- or 6-membered heteroaryl contains 1 or 2 heteroatoms individually selected from N, S or O, with the proviso that no more than one is O or S; and wherein any of said phenyl, and said 5- or 6-membered heteroaryl are unsubstituted or substituted by 1 , 2 or 3 substituents independently selected from halogen, cyano, Ci-C4-alkyl, Ci-C4-haloalkyl, or Ci-C4-alkoxy; and

R⁸ is selected from hydrogen, Ci-C4-alkyl, Ci-C4-alkoxy, Ci-C4-alkoxy-Ci-C4-alkyl, cyano-Ci-C4-alkyl, Ci-C4-alkylcarbonyl, Ci-C4-alkoxycarbonyl, Ci-C4-haloalkoxycarbonyl, Ci-C4-alkylcarbonyloxy-Ci-C4- alkyl, N,N-di(Ci-C4-alkyl)aminocarbonyl, or Cs-Ce-cycloalkyloxycarbonyl; or a salt or an N-oxide thereof.

2. The compound according to claim 1 , wherein R² is hydrogen, and R³ is hydrogen or Ci-Cs-alkyl.

3. The compound according to any of claims 1 or claim 2, wherein R⁴ is hydrogen, or halogen.

4. The compound according to any of claims 1 to 3, wherein R⁵ and R⁶ are independently selected from hydrogen, or methyl; or R⁵ and R⁶ together with the carbon to which they are attached represent a cyclopropyl group.

5. The compound according to any of claims 1 to 4, wherein R⁷ is Ci-C2-haloalkyl; and R⁸ is hydrogen, Ci-Cs-alkoxy-Ci-Cs-alkyl or Ci-Cs-alkylcarbonyl.

6. The compound according to any of claims 1 to 5, wherein R⁷ is dichloromethyl, difluoromethyl, or trifluoromethyl.

7. The compound according to any of claims 1 to 6, wherein and R⁸ is hydrogen.

8. The compound according to any of claims 1 to 7, wherein R¹ is Ci-C4-alkyl, Ci-Cs-haloalkyl, C3-C6- cycloalkyl, Cs-Ce-halocycloalkyl, cyano-Ci-C2-alkyl, C3-C6-cycloalkyl-Ci-C2-alkyl, cyano-Cs-Ce- cycloalkyl, Ci-Cs-alkoxy, Ci-C2-haloalkoxy, C2-C3-alkynyloxy, Ci-C2-alkoxy-Ci-C3-alkyl, Ci-C2-alkoxy- Ci-C2-alkoxy, C3-C6-cycloalkyl-Ci-C2-alkoxy, Cs-Ce-cycloalkyloxy, N,N-di(Ci-C2-alkyl)amino, C1-C2- alkoxyamino-Ci-C2-alkyl, Ci-C2-alkylsulfonyl-Ci-C2-alkyl, Ci-C2-alkylsulfanyl-Ci-C2-alkyl, C1-C2- alkoxyimino, Ci-C2-alkoxycarbonyl-Ci-C2-alkyl, Ci-C2-alkylcarbonyloxy-Ci-C2-alkyl, C1-C2- alkylcarbonylamino-Ci-C2-alkyl, Ci-C2-alkoxycarbonylamino-Ci-C2-alkyl, phenoxy-Ci-C2-alkyl, C4-C8- bicycloalkyl, 4-, 5-, or 6-membered heterocycloalkyl, phenyl-Ci-C2-alkyl, or 5- or 6-membered heteroaryl-Ci-C2-alkyl; wherein any of said 4-, 5-, or 6-membered heterocycloalkyl contains one heteroatom or one group selected from N, O, S, S=O, or SO2; wherein any of said 5- or 6-membered heteroaryl contains one heteroatom selected from N, S or O, or 2 to 4 nitrogens, wherein said C3-C6- cycloalkyl is unsubstituted or substituted by 1 , or 2 substituents independently selected from cyano, or Ci-Cs-alkyl; and wherein said phenyl and 5- or 6-membered heteroaryl are unsubstituted or substituted by 1 , or 2 substituents independently selected from halogen, cyano, Ci-Cs-alkyl, Ci-C2-haloalkyl, or C1- Cs-alkoxy.

9. The compound according to any of claims 1 to 7, wherein R¹ is Ci-C4-alkyl, Ci-Cs-haloalkyl, C3-C6- cycloalkyl, Cs-Ce-halocycloalkyl, cyano-Ci-C2-alkyl, C3-C6-cycloalkyl-Ci-C2-alkyl, cyano-Cs-Ce- cycloalkyl, Ci-Cs-alkoxy, Ci-C2-haloalkoxy, Ci-C2-alkoxy-Ci-C3-alkyl, Cs-Ce-cycloalkyloxy, C3-C6- cycloalkyl-Ci-C2-alkoxy, Ci-C2-alkylsulfonyl-Ci-C2-alkyl, N,N-di(Ci-C2-alkyl)amino, C1-C2- alkylcarbonylamino-Ci-C2-alkyl, phenoxy-Ci-C2-alkyl, 5-membered heterocycloalkyl, phenyl-Ci-C2- alkyl, or 5-membered heteroaryl-Ci-C2-alkyl; wherein said 5-membered heterocycloalkyl contains one heteroatom or one group selected from N, O, S, S=O, or SO2; wherein said 5-membered heteroaryl contains one heteroatom selected from N, S or O, or 2 to 4 nitrogens; and wherein said phenyl is unsubstituted or substituted by 1 , or 2 substituents independently selected from chloro or fluoro.

10. The compound according to any of claims 1 to 7, wherein R¹ is Ci-C4-alkyl, Ci-C4-haloalkyl, C3-C6- cycloalkyl, cyano-Ci-Cs-alkyl, Ci-C4-alkoxy, Ci-Cs-alkoxy-Ci-Cs-alkyl, Ci-Cs-haloalkoxy, or Cs-Cs- bicycloalky I, wherein said Cs-Ce-cycloalkyl is unsubstituted or substituted by 1 , 2 or 3 substituents independently selected from halogen, cyano, Ci-Cs-alkyl, or Ci-Cs-haloalkyl, in particular cyano and methyl.

11. A composition comprising a compound as defined in any one of claims 1 to 10.

12. The composition according to claim 11 , further comprising at least one additional active ingredient and/or an agrochemically-acceptable diluent or carrier.

13. A method of combating and controlling insects, acarines or molluscs which comprises applying to a pest, to a locus of a pest, or to a plant susceptible to attack by a pest an insecticidally, acaricidally, or molluscicidally effective amount of a compound of formula (I) as defined in any one of claims 1 to 10 or a composition as defined in claim 11 or 12.

14. A method for the protection of plant propagation material from the attack by insects, acarines, or molluscs, which comprises treating the propagation material or the site, where the propagation material is planted, with an effective amount of a compound of formula (I) as defined in any one of claims 1 to 10 or a composition as defined in claim 1 1 or 12.

15. A plant propagation material, such as a seed, comprising, or treated with or adhered thereto, a compound of formula (I) as defined in any one of claims 1 to 10.