Benzoxazole derivatives as pesticidal compounds

Abstract

The invention relates to a compound of formula (I), wherein the variables are defined in the specification. It also relates to a pesticidal mixture comprising the compound of formula (I); the use of compounds of formula (I) as an agrochemical pesticide; a method for combating or controlling invertebrate pests, a method for protecting growing plants from attack or infestation by invertebrate pests, seed comprising a compound of the formula (I); the use of a compound of the formula (I) for protecting growing plants from attack or infestation by invertebrate pests; and a method for treating or protecting an animal from infestation or infection by invertebrate pests.

Description

[0001] BASF SE 240867W001

[0002] B19464WO

[0003] 1

[0004] Benzoxazole derivatives as pesticidal compounds

[0005] Description

[0006] The invention relates to compounds of formula (I) or an agrochemically or veterinarily acceptable salt, stereoisomer, tautomer, or N-oxide thereof wherein the variables are as defined below. The invention also relates to the use of compounds of formula (I) as an agrochemical pesticide; to pesticidal compositions comprising a compound of formula (I) and another pesticidal ingredient; to a method for combating or controlling invertebrate pests, which method comprises contacting said pest or its food supply, habitat or breeding grounds with a pesticidally effective amount of at least one compound of the formula (I), the pesticidal mixture; to a method for protecting growing plants from attack or infestation by invertebrate pests, which method comprises contacting a plant, or soil or water in which the plant is growing, with a pesticidally effective amount of at least one compound of the formula (I) or the pesticidal mixture; and to seeds comprising a compound of the formula (I) or the pesticidal composition in an amount of from 0.1 g to 10 kg per 100 kg of seeds; to a use of a compound of the formula (I) or of the pesticidal compositions, for protecting growing plants from attack or infestation by invertebrate pests; and to a method for treating or protecting an animal from infestation or infection by invertebrate pests which comprises bringing the animal in contact with a pesticidally effective amount of a compound of the formula (I).

[0007] Invertebrate pests and in particular insects, arachnids and nematodes destroy growing and harvested crops and attack wooden dwelling and commercial structures, thereby causing large economic loss to the food supply and to property. Accordingly, there is an ongoing need for new agents for combating invertebrate pests.

[0008] WO2024085225 discloses the crystal structure of a bicyclic benzoxazole pyrimidinyl compound which has pesticidal activity. The invention differs from this compound in the nature of the residue R3. WO2022186133 and JP2017178820 disclose certain benzoxazole sulfone compounds with pesticidal activity.

[0009] Due to the ability of target pests to develop resistance to pesticidally-active agents, there is an ongoing need to identify further compounds, which are suitable for combating invertebrate pests such as insects, arachnids and nematodes. Furthermore, there is a need for new compounds having a high pesticidal activity and showing a broad activity spectrum against a large number of different invertebrate pests, especially against difficult to control insects, arachnids and nematodes. Furthermore, there is a need for compounds that are environmentally friendly and display a favorable toxicological profile.

[0010] It is therefore an object of the invention to identify and provide compounds, which exhibit a high BASF SE 240867W001

[0011] B19464WO pesticidal activity, have a broad activity spectrum against invertebrate pests, and show environmentally and toxicologically advantageous characteristics.

[0012] It has been found that these objects can be achieved by substituted bicyclic compounds of formula (I), as depicted and defined below, including their stereoisomers, their salts, in particular their agriculturally or veterinarily acceptable salts, their tautomers and their N-oxides.

[0013] In a first aspect, the invention relates to a compound of formula (I), wherein wherein

[0014] R1is S(O)m-Ci-C4-alkyl, S(O)m-C3-C6-cycloalkyl, S(O)m-C3-C6-cycloalkyl-Ci-C4-alkyl, which are unsubstituted or halogenated; S(O)(=NH)RM, S(O)(=NRM)RM;

[0015] Ci-C4-alkyl, Cs-Ce-cycloalkyl, Ci-C4-alkoxy, -O-Cs-Ce-cycloalkyl, all of which are unsubstituted, partially halogenated or fully halogenated;

[0016] Rwis Ci-C4-alkyl, cyclopropyl, C3-C6-cycloalkyl-Ci-C4-alkyl; m is 0, 1 or 2; n is 0, 1 or 2;

[0017] R2is Ci-C4-alkyl, Ci-C4-alkoxy, Cs-Ce-cycloalkyl, halogen, cyano, NHRM, N(RM)2, NH-CO- RM, CO-NH2, CO-NHRM, CO-N(RM)2; or phenyl which is unsubstituted or substituted with at least one Ci-C4-alkyl which is unsubstituted or partially or fully halogenated; Cs-Ce-cycloalkyl, halogen, O-S(O)2-RM, CN, Ci-Cs-alkoxy, which is unsubstituted or partially or fully halogenated, C3-C6- cycloalkoxy; N=S(O)(RM)2 or a five- or six-membered heterocycle, which is saturated, partially unsaturated, or fully unsaturated, and which is unsubstituted or substituted with at least one halogen, CN, Ci-C4-alkyl which is unsubstituted or partially or fully halogenated; C3-C6- cycloalkyl, Ci-Cs-alkoxy, which is unsubstituted or partially or fully halogenated;

[0018] R3is

[0019] (1) Cs-Ce-cycloalkyl, which is unsubstituted or partially or fully halogenated; or halogen;

[0020] (2) phenyl substituted with (a) one R4, or (b) substituted with one R4and one halogen, or (c) substituted with up to 5 halogens;

[0021] (3) 1 ,3-benzodioxole which is unsubstituted or partly or fully halogenated;

[0022] (4) a six-membered saturated, partially unsaturated, or fully unsaturated heterocyclic ring or ring system, wherein said heterocyclic ring or ring system comprises one, two or three, same or different heteroatoms O or N which may be unsubstituted or substituted with Ci-C4-alkyl, and is unsubstituted, or substituted with one R4, or substituted with two halogens;

[0023] (5) or Ci-C4-alkynyl, which is unsubstituted or substituted with Cs-Ce-cycloalkyl or Si(R5)3; wherein R5is Ci-C4-alkyl; or

[0024] (6) a five-membered saturated, partially unsaturated, or fully unsaturated heterocyclic ring, wherein said heterocyclic ring comprises one, two or three, same or different BASF SE 240867W001

[0025] B19464WO

[0026] 3 heteroatoms selected from N, O, and S, wherein N may be unsubstituted or substituted with Ci-C4-alkyl, Cs-Ce-cycloalkyl, C-bound Ci-C4-alkoxy, Ci-C4-alkyl-Ci-C4-alkoxy; wherein the five-membered ring is unsubstituted or substituted with one R4,

[0027] R4is halogen, cyano, Ci-C4-alkyl, which is unsubstituted or partially or fully halogenated; NH-CO-RM;

[0028] Cs-Ce-cycloalkyl;

[0029] Ci-C4-alkoxy-Ci-C4-alkyl, Cs-Ce-cycloalkyl-Ci-Cs-alkoxy, Ci-C4-alkoxy-Ci-C4-alkoxy-Ci- C4-alkyl;

[0030] C(RM)2-CN, CHRM-CN, C(RM)2-(CONH2), CHRM-(CONH2), C(RM)2-(CSNH2), CHRM- (CSNH2), l-cyano-Cs-Ce-cycloalkyl, l-Cs-Ce-cycloalkyl-carboxamide, I-C3-C6- cycloalkyl-thiocarboxamide,

[0031] O-CH2-CN, O-CHRM-CN, O-C(RM)2-CN, O-C(RM)2-(CONH2), O-C(RM)2-(CSNH2), O-l-cyano-Cs-Ce-cycloalkyl, O-C(CONH2)-C3-C6-cycloalkyl, O-C(CSNH2)-C3-Ce- cycloalkyl;

[0032] O-S(O)2-RM;

[0033] Ci-Cs-alkoxy, which is unsubstituted or partially or fully halogenated; Cs-Ce-cycloalkyl- Ci-Cs-alkoxy which is unsubstituted or partially or fully halogenated, Cs-Ce-cycloalkoxy, which is unsubstituted or partially or fully halogenated;

[0034] S-RM, SO-RM; SO2-RM;S(O)(=NRM)RM, S(O)(=NH)RM,

[0035] N=S(O)(RM)2, CO-N=SO(RM)2,

[0036] SF5, (=O), C(=O)H, C(=O)RM, difluoromethylen, each RMis independently Ci-Cs-alkyl which is unsubstituted or partially or fully halogenated; or Cs-Ce-cycloalkyl, or Cs-Ce-cycloalkyl in which at least one C is replaced by a heteroatom; or in case of two adjacent substituents RM, the substituents may form a ring together by a C2-Ce-alkyl bridge, which is unsubstituted or partly or fully halogenated and in which one or more carbon atoms may be replaced by O or N; and the N-oxides, stereoisomers, tautomers and agriculturally or veterinarily acceptable salts thereof.

[0037] The compounds of the formula (I), and their agriculturally acceptable salts are highly active against animal pest, i.e. harmful arthropodes and nematodes, especially against insects and acaridae which are difficult to control by other means.

[0038] Moreover, the invention relates to and includes the following embodiments:

[0039] - compositions comprising at least one compound of formula (I) as defined above and a liquid or solid carrier;

[0040] - agricultural and veterinary compositions comprising an amount of at least one compound of formula (I) or an enantiomer, diasteromer or salt thereof as defined above;

[0041] - methods for combating invertebrate pests, infestation, or infection by invertebrate pests, which method comprises contacting said pest or its food supply, habitat or breeding grounds with a pesticidally effective amount of at least one compound of formula (I) as defined above or a composition thereof;

[0042] - methods for controlling invertebrate pests, infestation, or infection by invertebrate pests, which method comprises contacting said pest or its food supply, habitat or breeding grounds with a BASF SE 240867W001

[0043] B19464WO

[0044] 4 pesticidally effective amount of at least one compound of formula (I) as defined above or a composition comprising at least one compound of formula (I);

[0045] - methods for preventing or protecting against invertebrate pests comprising contacting the invertebrate pests, or their food supply, habitat or breeding grounds with substituted imidazolium compounds of the general formula (I) as defined above or a composition comprising at least one compound of formula (I) as defined above or a composition comprising at least one compound of formula (I);

[0046] - methods for protecting crops, plants, plant propagation material and / or growing plants from attack or infestation by invertebrate pests comprising contacting or treating the crops, plants, plant propagation material and growing plants, or soil, material, surface, space, area or water in which the crops, plants, plant propagation material is stored or the plant is growing, with a pesticidally effective amount of at least one compound of formula (I) as defined above or a composition comprising at least one compound of formula (I);

[0047] - non-therapeutic methods for treating animals infested or infected by parasites or preventing animals of getting infected or infested by parasites or protecting animals against infestation or infection by parasites which comprises orally, topically or parenterally administering or applying to the animals a parasiticidally effective amount of a compound of formula (I) as defined above or a composition comprising at least one compound of formula (I);

[0048] - methods for treating, controlling, preventing or protecting animals against infestation or infection by parasites by administering or applying orally, topically or parenterally to the animals a compound of the general formula (I) as defined above or a composition comprising at least one compound of formula (I);

[0049] - seed comprising a compound of formula (I) as defined above, in an amount of from 0.1g to 10kg per 100kg of seed;

[0050] - the use of the compounds of formula (I) as defined above for protecting growing plants or plant propagation material from attack or infestation by invertebrate pests;

[0051] - the use of compounds of formula (I) or the enantiomers, diastereomers or veterinary acceptable salts thereof for combating parasites in and on animals;

[0052] - a process for the preparation of a veterinary composition for treating, controlling, preventing or protecting animals against infestation or infection by parasites which comprises adding a parasiticidally effective amount of a compound of formula (I) or the enantiomers, diastereomers and / or veterinary acceptable salt thereof to a carrier composition suitable for veterinary use;

[0053] - the use of a compound of formula (I) or the enantiomers, diastereomers and / or veterinary acceptable salt thereof for the preparation of a medicament for treating, controlling, preventing or protecting animals against infestation or infection by parasites.

[0054] All the compounds of formula (I) and, if applicable, their stereoisomers, their tautomers, their salts or their N-oxides as well as compositions thereof are particularly useful for controlling invertebrate pests, in particular for controlling arthropods and nematodes and especially insects. Therefore, the invention relates to the use of a compound of formula (I) as an agrochemical pesticide, preferably for combating or controlling invertebrate pests, in particular invertebrate pests of the group of insects, arachnids or nematodes.

[0055] The term "compound(s) according to the invention" or "compound(s) of formula (I)" as used in the invention refers to and comprises the compound(s) as defined herein and / or BASF SE 240867W001

[0056] B19464WO

[0057] 5 stereoisomer(s), salt(s), tautomer(s) or N-oxide(s) thereof. The term "compound(s) of the invention" is to be understood as equivalent to the term "compound(s) according to the invention", therefore also comprising stereoisomer(s), salt(s), tautomer(s) or N-oxide(s) of compounds of formula (I). As used herein, the term “compound(s) of the invention” or “compound(s) according to the invention” refers to the compound(s) of formula (I) as defined above, which are also referred to as “compound(s) of formula I” or “compound(s) I” or “formula I compound(s)”, and includes their salt(s), tautomer(s), stereoisomer(s), and N-oxide(s). The term "composition(s) according to the invention" or "composition(s) of the invention" encompasses composition(s) comprising at least one compound of formula (I) according to the invention as defined above, therefore also including a stereoisomer, an agriculturally or veterinary acceptable salt, tautomer or an N-oxide of the compounds of formula (I). The compounds of the invention may be amorphous or may exist in one or more different crystalline states (polymorphs) or modifications which may have a different macroscopic properties such as stability or show different biological properties such as activities. The invention includes both amorphous and crystalline compounds of the formula (I), mixtures of different crystalline states or modifications of the respective compound I, as well as amorphous or crystalline salts thereof.

[0058] The compounds of the formula (I) may have one or, depending on the substitution pattern, more centers of chirality, in which case they are present as mixtures of enantiomers or diastereomers. The invention provides both the single pure enantiomers or pure diastereomers of the compounds of formula (I), and their mixtures and the use according to the invention of the pure enantiomers or pure diastereomers of the compound of formula (I) or its mixtures. Suitable compounds of the formula (I) also include all possible geometrical stereoisomers (cis / trans isomers) and mixtures thereof. Cis / trans isomers may be present with respect to an alkene, carbon-nitrogen double-bond or amide group. The term "stereoisomer(s)" encompasses both optical isomers, such as enantiomers or diastereomers, the latter existing due to more than one center of chirality in the molecule, as well as geometrical isomers (cis / trans isomers). The invention relates to every possible stereoisomer of the compounds of formula (I), i.e. to single enantiomers or diastereomers, as well as to mixtures thereof.

[0059] Depending on the substitution pattern, the compounds of the formula (I) may be present in the form of their tautomers. Hence the invention also relates to the tautomers of the formula (I) and the stereoisomers, salts, tautomers and N-oxides of said tautomers.

[0060] Salts of the compounds of the formula (I) are preferably agriculturally and / or veterinary acceptable salts. They can be formed in a customary method, e.g. by reacting the compound with an acid of the anion in question if the compound of formula (I) has a basic functionality or by reacting an acidic compound of formula (I) with a suitable base.

[0061] Suitable agriculturally or veterinary useful salts are especially the salts of those cations or the acid addition salts of those acids whose cations and anions, respectively, do not have any adverse effect on the action of the compounds according to the invention. Suitable cations are in particular the ions of the alkali metals, preferably lithium, sodium and potassium, of the alkaline earth metals, preferably calcium, magnesium, and barium, and of the transition metals, preferably manganese, copper, zinc and iron, and also ammonium (NH4+) and substituted ammonium in which one to four of the hydrogen atoms are replaced by Ci-C4-alkyl, C1-C4- hydroxyalkyl, Ci-C4-alkoxy, Ci-C4-alkoxy-Ci-C4-alkyl, hydroxy-Ci-C4-alkoxy-Ci-C4-alkyl, phenyl BASF SE 240867W001

[0062] B19464WO

[0063] 6 or benzyl. Examples of substituted ammonium ions comprise methylammonium, isopropylammonium, dimethylammonium, diisopropylammonium, trimethylammonium, tetramethylammonium, tetraethylammonium, tetrabutylammonium, 2-hydroxyethylammonium, 2-(2-hydroxyethoxy)ethyl-ammonium, bis(2-hydroxyethyl)ammonium, benzyltrimethylammonium and benzyltriethylammonium, furthermore phosphonium ions, sulfonium ions, preferably tri(Ci- C4-alkyl)sulfonium, and sulfoxonium ions, preferably tri(Ci-C4-alkyl)sulfoxonium.

[0064] Anions of useful acid addition salts are primarily chloride, bromide, fluoride, hydrogen sulfate, sulfate, dihydrogen phosphate, hydrogen phosphate, phosphate, nitrate, hydrogen carbonate, carbonate, hexafluorosilicate, hexafluorophosphate, benzoate, and the anions of Ci-C4-alkanoic acids, preferably formate, acetate, propionate and butyrate. They can be formed by reacting the compounds of the formulae I with an acid of the corresponding anion, preferably of hydrochloric acid, hydrobromic acid, sulfuric acid, phosphoric acid or nitric acid.

[0065] The term “N-oxide” includes any compound of the invention which has at least one tertiary nitrogen atom that is oxidized to an N-oxide moiety.

[0066] The organic moieties groups mentioned in the above definitions of the variables are - like the term halogen - collective terms for individual listings of the individual group members. The prefix Cx-Cy indicates in each case the possible number of carbon atoms in the group. "Halogen" will be taken to mean F, Cl, Br, and I, preferably F, Cl, Br.

[0067] The terms compound(s) of formula (x) and compound(s) (x), wherein x is a roman or arab number are used herein interchangeably and refer to a single or several compounds as defined by the respective formula (x).

[0068] The term “substituted with”, e.g. as used in "partially, or fully substituted with" means that one or more, e.g. 1 , 2, 3, 4 or 5 or all of the hydrogen atoms of a given radical have been replaced by one or more, same or different substituents as subsequently defined. Accordingly, for substituted cyclic moieties, e.g. 1 -cyanocyclopropyl, one or more of the hydrogen atoms of the cyclic moiety may be replaced by one or more, same or different substituents.

[0069] The term "Cx-Cy-alkyl" as used herein (and also in Cx-Cy-alkylamino, di-Cx-Cy-alkylamino, Cx-Cy- alkylaminocarbonyl, di-(Cx-Cy-alkylamino)carbonyl, Cx-Cy-alkylthio, Cx-Cy-alkylsulfinyl and Cx-Cy- alkylsulfonyl) refers to a branched or unbranched saturated hydrocarbon group having n to m, e.g. 1 to 10 carbon atoms, preferably 1 to 6 carbon atoms, e.g. methyl, ethyl, propyl, 1- methylethyl, butyl, 1 -methylpropyl, 2-methylpropyl, 1 ,1 -dimethylethyl, pentyl, 1 -methylbutyl, 2- methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1 -ethylpropyl, hexyl, 1 ,1 -dimethylpropyl, 1 ,2-di- methylpropyl, 1 -methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1 ,1 -dimethylbutyl, 1 ,2-dimethylbutyl, 1 ,3-di methyl butyl, 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, 1- ethyl-2-methylpropyl, heptyl, octyl, 2-ethylhexyl, nonyl and decyl and their isomers. Ci-C4-alkyl means for example methyl, ethyl, propyl, 1 -methylethyl, butyl, 1 -methylpropyl, 2-methylpropyl or 1 ,1 -dimethylethyl.

[0070] The term "Cx-Cy-haloalkyl" as used herein (and also in Cx-Cy-haloalkylsulfinyl and Cx-Cy-halo- alkylsulfonyl) refers to a straight-chain or branched alkyl group having n to m carbon atoms, e.g. 1 to 10 in particular 1 to 6 carbon atoms (as mentioned above), where some or all of the hydrogen atoms in these groups may be replaced by halogen atoms as mentioned above, e.g. C1-C4- haloalkyl, such as chloromethyl, bromomethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1- BASF SE 240867W001

[0071] B19464WO

[0072] 7 chloroethyl, 1-bromoethyl, 1 -fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2- chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl, pentafluoroethyl and the like. The term Ci-Cw-haloalkyl in particular comprises Ci-C2-fluoro- alkyl, which is synonym with methyl or ethyl, wherein 1 , 2, 3, 4 or 5 hydrogen atoms are substituted with fluorine atoms, such as fluoromethyl, difluoromethyl, trifluoromethyl, 1 -fluoro- ethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl and pentafluoromethyl.

[0073] Similarly, "Cx-Cy-alkoxy" and "Cx-Cy-alkylthio" (or Cx-Cy-alkylsulfenyl, respectively) refer to straight-chain or branched alkyl groups having n to m carbon atoms, e.g. 1 to 10, in particular 1 to 6 or 1 to 4 carbon atoms (as mentioned above) bonded through oxygen (or sulfur linkages, respectively) at any bond in the alkyl group. Examples include Ci-C4-alkoxy such as methoxy, ethoxy, propoxy, isopropoxy, butoxy, sec-butoxy, isobutoxy and tert-butoxy, further C1-C4- alkylthio such as methylthio, ethylthio, propylthio, isopropylthio, and n-butylthio.

[0074] Accordingly, the terms "Cx-Cy-haloalkoxy" and "Cx-Cy-haloalkylthio" (or Cx-Cy-haloalkylsulfenyl, resp.) refer to straight-chain or branched alkyl groups having n to m carbon atoms, e.g. 1 to 10, in particular 1 to 6 or 1 to 4 carbon atoms (as mentioned above) bonded through oxygen or sulfur linkages, resp., at any bond in the alkyl group, where some or all of the hydrogen atoms in these groups may be replaced by halogen atoms as mentioned above, e.g. Ci-C2-haloalkoxy, such as chloromethoxy, bromomethoxy, dichloromethoxy, trichloromethoxy, fluoromethoxy, difluoromethoxy, trifluoromethoxy, chlorofluoromethoxy, dichlorofluoromethoxy, chlorodifluoromethoxy, 1 -chloroethoxy, 1 -bromoethoxy, 1 -fluoroethoxy, 2-fluoroethoxy, 2,2-difluoroethoxy, 2,2,2-trifluoroethoxy, 2-chloro-2-fluoroethoxy, 2-chloro-2,2-difluoroethoxy, 2,2-dichloro-2-fluoro- ethoxy, 2,2,2-trichloroethoxy and pentafluoroethoxy, further Ci-C2-haloalkylthio, such as chloromethylthio, bromomethylthio, dichloromethylthio, trichloromethylthio, fluoromethylthio, difluoromethylthio, trifluoromethylthio, chlorofluoromethylthio, dichlorofluoromethylthio, chlorodifluoromethylthio, 1 -chloroethylthio, 1 -bromoethylthio, 1 -fluoroethylthio, 2-fluoroethylthio, 2,2-difluoro- ethylthio, 2,2,2-trifluoroethylthio, 2-chloro-2-fluoroethylthio, 2-chloro-2,2-difluoroethylthio, 2,2- dichloro-2-fluoroethylthio, 2,2,2-trichloroethylthio and pentafluoroethylthio and the like. Similarly, the terms Ci-C2-fluoroalkoxy and Ci-C2-fluoroalkylthio refer to Ci-C2-fluoroalkyl which is bound to the remainder of the molecule via an oxygen atom or a sulfur atom, respectively.

[0075] The suffix “-carbonyl” in a group or “C(=O)” denotes in each case that the group is bound to the remainder of the molecule via a carbonyl C=O group. This is the case e.g. in alkylcarbonyl, haloalkylcarbonyl, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, alkoxycarbonyl, haloalkoxycarbonyl, alkylcarbonylamino, and hydroxycarbonyl. For example, a hydroxycarbonyl group would refer to a carbonic acid group -C(=O)OH, and an aminocyrbonyl group would refer to an amide group -C(=O)NH2, both of which are bound to the remainder of the molecule via the carbonyl “C=O” group.

[0076] The term "aryl" as used herein refers to a mono-, bi- or tricyclic aromatic hydrocarbon radical such as phenyl or naphthyl, in particular phenyl (also referred as to CeHs as subsitituent). The term "C3-Cy-cycloalkyl" as used herein refers to a monocyclic ring of 3- to y-membered saturated cycloaliphatic radicals, e.g. cyclopropyl (CC3H5), cyclobutyl (CC4H7), cyclopentyl (CC5H9), cyclohexyl (cCeHn), cycloheptyl, cyclooctyl and cyclodecyl.

[0077] Accordingly, the term “C3-Cy-cycloalkoxy” as used herein refers to a “C3-Cy”-cycloalkyl moiety which is bonded to the rest of the molecule via an oxygen atom, such as in cyclopropoxy, cyclobutoxy, cyclopentoxy and cyclohexoxy. BASF SE 240867W001

[0078] B19464WO

[0079] 8

[0080] The term "cycloalkylalkyl" denotes as well as the term “alkyl which may be substituted with cycloalkyl” an alkyl group which is substituted with a cycloalkyl ring, wherein alkyl and cycloakyl are as herein defined.

[0081] The term "Cs-Cy-cycloalkenyl" as used herein refers to a monocyclic ring of 3- to y-membered partially unsaturated cycloaliphatic radicals.

[0082] The term "cycloalkylcycloalkyl" denotes as well as the term “cycloalkyl which may be substituted with cycloalkyl” a cycloalkyl substitution on another cycloalkyl ring, wherein each cycloalkyl ring independently has from 3 to 7 carbon atom ring members and the cycloalkyls are linked through one single bond or have one common carbon atom. Examples of cycloalkylcycloalkyl include cyclopropylcyclopropyl (e.g. 1 ,1'-bicyclopropyl-2-yl), cyclohexylcyclohexyl wherein the two rings are linked through one single common carbon atom (e.g. 1 ,1'-bicyclohexyl-2-yl), cyclohexylcyclopentyl wherein the two rings are linked through one single bond (e.g. 4- cyclopentylcyclohexyl) and their different stereoisomers such as (1 R,2S)-1 , T-bicyclopropyl-2-yl and (1R,2R)-1 ,1'-bicyclopropyl-2-yl.The term “carbocycle” or “carbocyclyl” includes, unless otherwise indicated, in general a 3- to 12-membered, preferably a 3- to 8-membered or a 5- to 8-membered, more preferably a 5- or 6-membered mono-cyclic, ring comprising 3 to 12, preferably 3 to 8 or 5 to 8, more preferably 5 or 6 carbon atoms.

[0083] The carbocyclic radicals may be saturated, partially unsaturated, or fully unsaturated. Preferably, the term “carbocycle” covers cycloalkyl and cycloalkenyl groups as defined above, for example cyclopropane, cyclobutane, cyclopentane and cyclohexane rings. When it is referred to “fully unsaturated” carbocycles, this term also includes “aromatic” carbocycles. In certain preferred embodiments, a fully unsaturated carbocycle is an aromatic carbocycle as defined below, preferably a 6-membered aromatic carbocycle.

[0084] The term "hetaryl" or “aromatic heterocycle” or “aromatic heterocyclic ring” includes monocyclic 5- or 6-membered heteroaromatic radicals comprising as ring members 1 , 2, 3, or 4 heteroatoms selected from N, O, and S. Examples of 5- or 6-membered heteroaromatic radicals include pyridyl, i.e. 2-, 3-, or 4-pyridyl, pyrimidinyl, i.e. 2-, 4- or 5-pyrimidinyl, pyrazinyl, pyridazinyl, i.e. 3- or 4-pyridazinyl, thienyl, i.e. 2- or 3-thienyl, furyl, i.e. 2-or 3-furyl, pyrrolyl, i.e. 2- or 3-pyrrolyl, oxazolyl, i.e. 2-, 3- or 5-oxazolyl, isoxazolyl, i.e. 3-, 4- or 5-isoxazolyl, thiazolyl, i.e. 2-, 3- or 5-thiazolyl, isothiazolyl, i.e. 3-, 4- or 5-isothiazolyl, pyrazolyl, i.e. 1-, 3-, 4- or 5- pyrazolyl, i.e. 1-, 2-, 4- or 5-imidazolyl, oxadiazolyl, e.g. 2- or 5-[1,3,4]oxadiazolyl, 4- or 5-(1 ,2,3- oxadiazol)yl, 3- or 5-(1,2,4-oxadiazol)yl, 2- or 5-(1 ,3,4-thiadiazol)yl, thiadiazolyl, e.g. 2- or 5- (1 ,3,4-thiadiazol)yl, 4- or 5-(1 ,2,3-thiadiazol)yl, 3- or 5-(1,2,4-thiadiazol)yl, triazolyl, e.g. 1 H-, 2H- or 3H-1,2,3-triazol-4-yl, 2H-triazol-3-yl, 1 H-, 2H-, or 4H-1 ,2,4-triazolyl and tetrazolyl, i.e. 1 H- or 2H-tetrazolyl.

[0085] The terms “heterocycle”, "heterocyclyl" or “heterocyclic ring” includes, unless otherwise indicated, in general 3- to 12-membered, preferably 3- to 8-membered, 3- to 7-membered, or 5- to 8-membered, more preferably 5- or 6-membered, in particular 6-membered monocyclic heterocyclic radicals. The heterocyclic radicals may be saturated, partially unsaturated, or fully unsaturated. As used in this context, the term “fully unsaturated” also includes “aromatic”. In a preferred embodiment, a fully unsaturated heterocycle is thus an aromatic heterocycle, preferably a 5- or 6-membered aromatic heterocycle comprising one or more, e.g. 1 , 2, 3, or 4, preferably 1, 2, or 3 heteroatoms selected from N, O and S as ring members. Examples of aromatic heterocycles are provided above in connection with the definition of “hetaryl”. Unless BASF SE 240867W001

[0086] B19464WO

[0087] 9 otherwise indicated, “hetaryls” are thus covered by the term “heterocycles”. The heterocyclic non-aromatic radicals usually comprise 1 , 2, 3, 4 or 5, preferably 1 , 2 or 3 heteroatoms selected from N, O, and S as ring members, where S-atoms as ring members may be present as S, SO or SO2, and N-atoms may be oxidized, or non-oxidized. Examples of 5- or 6-membered heterocyclic radicals comprise saturated or unsaturated, non-aromatic heterocyclic rings, such as oxiranyl, oxetanyl, thietanyl, thietanyl-S-oxid (S-oxothietanyl), thietanyl-S-dioxid (S- dioxothiethanyl), pyrrolidinyl, pyrrolinyl, pyrazolinyl, tetrahydrofuranyl, dihydrofuranyl, 1 ,3- dioxolanyl, thiolanyl, S-oxothiolanyl, S-dioxothiolanyl, dihydrothienyl, S-oxodihydrothienyl, S- dioxodihydrothienyl, oxazolidinyl, oxazolinyl, thiazolinyl, oxathiolanyl, piperidinyl, piperazinyl, pyranyl, dihydropyranyl, tetrahydropyranyl, 1 ,3- and 1 ,4-dioxanyl, thiopyranyl, S. oxothiopyranyl, S-dioxothiopyranyl, dihydrothiopyranyl, S-oxodihydrothiopyranyl, S-dioxodihydrothiopyranyl, tetrahydrothiopyranyl, S-oxotetrahydrothiopyranyl, S-dioxotetrahydrothiopyranyl, morpholinyl, thiomorpholinyl, S-oxothiomorpholinyl, S-dioxothiomorpholinyl, thiazinyl and the like. Examples for heterocyclic ring also comprising 1 or 2 carbonyl groups as ring members comprise pyrrolidin-2-onyl, pyrrolidin-2,5-dionyl, imidazolidin-2-onyl, oxazolidin-2-onyl, thiazolidin-2-onyl and the like.

[0088] The terms “alkylene”, “alkenylene”, and “alkynylene” refer to alkyl, alkenyl, and alkynyl as defined above, respectively, which are bonded to the remainder of the molecule, via two atoms, preferably via two carbon atoms, of the respective group, so that they represent a linker between two moieties of the molecule. In particular, the term “alkylene” may refer to alkyl chains such as CH2CH2, -CH(CH3)-, CH2CH2CH2, CH(CH3)CH2, CH2CH(CH3), CH2CH2CH2CH2, CH2CH2CH2CH2CH2, CH2CH2CH2CH2CH2CH2, and CH2CH2CH2CH2CH2CH2CH2. Similarly, “alkenylene” and “alkynylene” may refer to alkenyl and alkynyl chains, respectively.

[0089] The term "5- to 6-membered carbocyclic ring" as used herein refers to cyclopentane and cyclohexane rings.

[0090] Examples of 5- or 6-membered saturated heterocyclic rings include: 2-tetrahydrofuranyl, 3- tetrahydrofuranyl, 2-tetrahydrothienyl, 3-tetrahydrothienyl, 2-pyrrolidinyl, 3-pyrrolidinyl, 3-pyrazo- lidinyl, 4-pyrazolidinyl, 5-pyrazolidinyl, 2-imidazolidinyl, 4-imidazolidinyl, 2-oxazolidinyl, 4-oxazo- lidinyl, 5-oxazolidinyl, 3-isoxazolidinyl, 4-isoxazolidinyl, 5-isoxazolidinyl, 2-thiazolidinyl, 4-thia- zolidinyl, 5-thiazolidinyl, 3-isothiazolidinyl, 4-isothiazolidinyl, 5-isothiazolidinyl, 1 ,2,4-oxadiazo- lidin-3-yl, 1 ,2,4-oxadiazolidin 5 yl, 1 ,2,4-thiadiazolidin-3-yl, 1 ,2,4-thiadiazolidin-5-yl, 1 ,2,4-triazo- lidin-3-yl ,- 1 ,3,4-oxadiazolidin-2-yl, 1 ,3,4-thiadiazolidin-2-yl, 1 ,3,4-triazolidin-2-yl, 2-tetrahydro- pyranyl, 4-tetrahydropyranyl, 1 ,3-dioxan-5-yl, 1 ,4-dioxan-2-yl, 2-piperidinyl, 3-piperidinyl, 4- piperidinyl, 3-hexahydropyridazinyl, 4-hexahydropyridazinyl, 2-hexahydropyrimidinyl, 4-hexa- hydropyrimidinyl, 5-hexahydropyrimidinyl, 2-piperazinyl, 1 ,3,5-hexahydrotriazin-2-yl and 1 ,2,4- hexahydrotriazin-3-yl, 2-morpholinyl, 3-morpholinyl, 2-thiomorpholinyl, 3-thiomorpholinyl, 1- oxothiomorpholin-2-yl, 1-oxothiomorpholin-3-yl, 1 ,1-dioxothiomorpholin-2-yl, 1 ,1-dioxothio- morpholin-3-yl.

[0091] Examples of 5- or 6-membered partially unsaturated heterocyclyl or heterocyclic rings include: 2,3-dihydrofur-2-yl, 2,3-dihydrofur-3-yl, 2,4-dihydrofur-2-yl, 2,4-dihydrofur-3-yl, 2,3-dihydrothien-

[0092] 2-yl, 2,3-dihydrothien-3-yl, 2,4-dihydrothien-2-yl, 2,4-dihydrothien-3-yl, 2-pyrrolin-2-yl, 2-pyrrolin-

[0093] 3-yl, 3-pyrrolin-2-yl, 3-pyrrolin-3-yl, 2-isoxazolin-3-yl, 3-isoxazolin-3-yl, 4-isoxazolin 3 yl, 2- isoxazolin-4-yl, 3-isoxazolin-4-yl, 4-isoxazolin-4-yl, 2-isoxazolin-5-yl, 3-isoxazolin-5-yl, 4- isoxazolin-5-yl, 2-isothiazolin-3-yl, 3-isothiazolin-3-yl, 4-isothiazolin-3-yl, 2-isothiazolin-4-yl, 3- BASF SE 240867W001

[0094] B19464WO

[0095] 10 isothiazolin-4-yl, 4-isothiazolin-4-yl, 2-isothiazolin-5-yl, 3-isothiazolin-5-yl, 4-isothiazolin-5-yl, 2,3 dihydropyrazol-1-yl, 2,3-dihydropyrazol-2-yl, 2,3-dihydropyrazol-3-yl, 2,3-dihydropyrazol-4-yl, 2,3-dihydropyrazol-5-yl, 3,4-dihydropyrazol-1-yl, 3,4-dihydropyrazol-3-yl, 3,4-dihydropyrazol-4- yl, 3,4-dihydropyrazol-5-yl, 4,5-dihydropyrazol-1-yl, 4,5-dihydropyrazol-3-yl, 4,5-dihydropyrazol- 4-yl, 4,5-dihydropyrazol-5-yl, 2,3-dihydrooxazol-2-yl, 2,3-dihydrooxazol-3-yl, 2,3-dihydrooxazol- 4-yl, 2,3-dihydrooxazol-5-yl, 3,4-dihydrooxazol-2-yl, 3,4-dihydrooxazol-3-yl, 3,4-dihydrooxazol-4- yl, 3,4-dihydrooxazol-5-yl, 3,4-dihydrooxazol-2-yl, 3,4-dihydrooxazol-3-yl, 3,4-dihydrooxazol-4- yl, 2-, 3-, 4-, 5- or 6-di- or tetrahydropyridinyl, 3-di- or tetrahydropyridazinyl, 4-di- or tetrahydropyridazinyl, 2-di- or tetrahydropyrimidinyl, 4-di- or tetrahydropyrimidinyl, 5-di- or tetrahydropyrimidinyl, di- or tetrahydropyrazinyl, 1,3, 5-di- or tetrahydrotriazin-2-yl.

[0096] Examples of 5- or 6-membered fully unsaturated heterocyclic (hetaryl) or heteroaromatic rings are: 2-furyl, 3-furyl, 2-thienyl, 3-thienyl, 2-pyrrolyl, 3-pyrrolyl, 3-pyrazolyl, 4-pyrazolyl, 5- pyrazolyl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 2-thiazolyl, 4-thiazolyl, 5-thiazolyl, 2-imidazolyl, 4- imidazolyl, 1 ,3,4-triazol-2-yl, 2-pyridinyl, 3-pyridinyl, 4-pyridinyl, 3-pyridazinyl, 4-pyridazinyl, 2- pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl and 2-pyrazinyl.

[0097] A "C2-Cy-alkylene" is divalent branched or preferably unbranched saturated aliphatic chain having 2 to m, e.g. 2 to 7 carbon atoms, for example CH2CH2, -CH(CH3)-, CH2CH2CH2, CH(CH3)CH2, CH2CH(CH3), CH2CH2CH2CH2, CH2CH2CH2CH2CH2, CH2CH2CH2CH2CH2CH2, and CH2CH2CH2CH2CH2CH2CH2.

[0098] The term “alkylamino” as used herein refers to a straight-chain or branched saturated alkyl group having 1 to 10 carbon atoms, preferably 1 to 4 carbon atoms, more preferably 1 to 3 carbon atoms, which is bonded via a nitrogen atom, e.g. an -NH- group.

[0099] The term “dialkylamino” as used herein refers to a straight-chain or branched saturated alkyl group having 1 to 10 carbon atoms, preferably 1 to 4 carbon atoms, more preferably 1 to 3 carbon atoms, which is bonded via a nitrogen atom, which is substituted by another straightchain or branched saturated alkyl group having 1 to 10 carbon atoms, preferably 1 to 4 carbon atoms, more preferably 1 to 3 carbon atoms, e.g. a methylamino or ethylamino group.

[0100] The term "alkylthio "(alkylsulfanyl: alkyl-S-)" as used herein refers to a straight-chain or branched saturated alkyl group having 1 to 10 carbon atoms, preferably 1 to 4 carbon atoms (= Ci-C4-alkylthio), more preferably 1 to 3 carbon atoms, which is attached via a sulfur atom. Examples include methylthio, ethylthio, propylthio, isopropylthio, and n-butylthio.

[0101] The term "haloalkylthio" as used herein refers to an alkylthio group as mentioned above wherein the hydrogen atoms are partially or fully substituted by fluorine, chlorine, bromine and / or iodine. Examples include chloromethylthio, bromomethylthio, dichloromethylthio, trichloromethylthio, fluoromethylthio, difluoromethylthio, trifluoromethylthio, chlorofluoromethylthio, dichlorofluoromethylthio, chlorodifluoromethylthio, 1 -chloroethylthio, 1 -bromoethylthio, 1- fluoroethylthio, 2-fluoroethylthio, 2,2-difluoroethylthio, 2,2,2-trifluoroethylthio, 2-chloro-2- fluoroethylthio, 2-chloro-2,2-difluoroethylthio, 2,2-dichloro-2-fluoroethylthio, 2,2,2-trichloroethyl- thio and pentafluoroethylthio and the like.

[0102] The term "alkylsulfinyl" (alkylsulfoxyl: Ci-Ce-alkyl-S(=O)-), as used herein refers to a straightchain or branched saturated alkyl group (as mentioned above) having 1 to 10 carbon atoms, preferably 1 to 4 carbon atoms (= Ci-C4-alkylsulfinyl), more preferably 1 to 3 carbon atoms bonded through the sulfur atom of the sulfinyl group at any position in the alkyl group. BASF SE 240867W001

[0103] B19464WO

[0104] 11

[0105] The term "(halo)alkylsulfonyl" (alkyl-S(=O)2-) as used herein refers to a straight-chain or branched saturated (and halogenated) alkyl group having 1 to 10 carbon atoms, preferably 1 to 4 carbon atoms (= Ci-C4-(halo)alkylsulfonyl), preferably 1 to 3 carbon atoms, which is bonded via the sulfur atom of the sulfonyl group at any position in the (halo)alkyl group.

[0106] The term "(halo)alkylsulfanyl" (alkyl-S-) as used herein refers to a straight-chain or branched saturated (and halogenated) alkyl group having 1 to 10 carbon atoms, preferably 1 to 4 carbon atoms (= Ci-C4-(halo)alkylsulfanyl), preferably 1 to 3 carbon atoms, which is bonded via the sulfur atom of the sulfanyl group at any position in the (halo)alkyl group.

[0107] The term "(halo)alkylsulfinyl" (alkyl-S(=O)-) as used herein refers to a straight-chain or branched saturated (and halogenated) alkyl group having 1 to 10 carbon atoms, preferably 1 to 4 carbon atoms (= Ci-C4-(halo)alkylsulfinyl), preferably 1 to 3 carbon atoms, which is bonded via the sulfur atom of the sulfinyl group at any position in the (halo)alkyl group.

[0108] Accordingly, the terms (halo)alkylsulfanylalkyl, (halo)alkylsulfi nylalkyl, and (halo)sulfonylalkyl as used for example in “Ci-C4-alkylsulfanyl-Ci-C4-alkyl”, “Ci-C4-alkylsulfinyl-Ci-C4-alkyl”, and “Ci- C4-alkylsulfonyl-Ci-C4-alkyl” relate to (halo)alkylsulfanyl-, (halo)alkylsulfinyl-, or (halo)alkylsulfonyl-groups that are bonded via the sulfur atom of the sulfanyl, the sulfinyl, or the sulfonyl group, respectively, to the alkyl group, which is in turn bonded to the rest of the molecule.

[0109] The term "alkylcarbonyl" (Ci-Ce-C(=O)-) refers to a straight-chain or branched alkyl group as defined above, which is bonded via the carbon atom of a carbonyl group (C=O) to the remainder of the molecule.

[0110] The term "alkoxycarbonyl" refers to an alkoxygroup group as defined above, which is bonded via the carbon atom of a carbonyl group (C=O) to the remainder of the molecule.

[0111] The term "alkylaminocarbonyl" (Ci-Ce-NH-C(=O)-) refers to a straight-chain or branched alkylamino group as defined above, which is bonded via the carbon atom of a carbonyl group (C=O) to the remainder of the molecule. Similarly, the term "dialkylaminocarbonyl" refers to a straight-chain or branched saturated alkyl group as defined above, which is bonded to a nitrogen atom, which is substituted with another straight-chain or branched saturated alkyl group as defined above, which nitrogen atom in turn is bonded via a carbonyl group (C=O) to the remainder of the molecule.

[0112] The term “S(O)(NRM)” refers to a group wherein RMis as defined for formula (I) and wherein the symbols and “§” mean the link to the remainder of the molecule.

[0113] The compounds of formula (I) can be prepared by standard methods of organic chemistry. If certain derivatives cannot be prepared by the processes outlined below, they can be obtained by derivatization of other compounds of formula (I) that are accessible by these methods. BASF SE 240867W001

[0114] B19464WO

[0115] 12

[0116] Compounds of formula (II), corresponding to compounds of formula (I) may be prepared by reaction of compounds of formula (III) with compounds of formula (IV) as displayed under Process 1 :

[0117] All variables in formulae (III), (IV), (V) and (II) have a meaning as defined for formula (I). Reactions of this type have been described in WO 2014123205.

[0118] The intermediate (V) is prepared by reacting (III) and (IV) at temperatures in the range of 0 to 120°C in an inert solvent in the presence of amide bond forming reagents such as such as DCC (dicyclohexyl-carbodiimide) and DIC (diisopropylcarbodiimide), benzotriazole derivatives, such as HATLI (O-(7- azabenzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate), HBTLI ((Obenzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate) and HCTLI (1 H-benzotriazolium-1-[bis(dimethylamino)methylene]-5-chloro tetrafluoroborate) and phosphonium-derived activators, such as BOP ((benzotriazol-l-yloxy)-tris(dimethylamino) phosphonium hexafluorophosphate), PyBOP ((benzotriazol-l-yloxy)-tripyrrolidinphosphonium hexafluorophosphate) and PyBrOP (bromotripyrrolidinphosphonium hexafluorophosphate). Suitable solvents are aliphatic hydrocarbons, such as pentane, hexane, cyclohexane, or petrol ether; aromatic hydrocarbons, such as benzene, toluene, o-, m-, and p-xylene; halogenated hydrocarbons, or halogenated aromatic C6-C10-hydrocarbons, such as CH2CI2, CHCI3, CCI4, CH2CICH2CI, CCI3CH3, CHCI2CH2CI, CCI2CCI2, or chlorobenzene; ethers, such as CH3CH2OCH2CH3, (CH3)2CHOCH(CH3)2, CH3OC(CH3)3(MTBE), CH3OCH3 (DME), CH3OCH2CH2OCH3, CH3OC(CH3)2CH2CH3, dioxane, anisole, 2-methyltetrahydrofuran, tetra hydrofuran (THF), and diethylene glycol; nitriles, such as CH3CN, and CH3CH2CN; alcohols, such as CH3OH, CH3CH2OH, CH3CH2CH2OH, CH3CH(OH)CH3, CH3(CH2)3OH, and C(CH3)3OH, CH2(OH)CH2(OH), and CH3CH(OH)CH2OH. Mixtures of the above solvents are also possible in presence of suitable bases such as pyrrolidine; tertiary amines, such as diisopropylethylamine, trimethylamine, triethylamine, triisopropylamine and N-methylpiperidine, imidazole, pyridine; substituted pyridines, such as collidine, lutidine and 4- dimethylaminopyridine, and polycyclic amides and amidines, such as 1 ,8-diazabicycloundec-7- ene (DBU), 1 ,4-Diazabicyclo[2.2.2]octane (DABCO) etc. The compound of present invention (II) can be produced by intramolecular condensation of intermediate (V). The reaction is carried out in an organic solvent such as benzene, toluene, o-, m-, and p-xylene; halogenated BASF SE 240867W001

[0119] B19464WO

[0120] 13 hydrocarbons, or halogenated aromatic Ce-Cw-hydrocarbons, CH3CH2CH2OH, CH3CH(OH)CH3, CH3(CH2)3OH, and C(CH3)OH, CH2(OH)CH2(OH), and CH3CH(OH)CH2OH, o-, m-, and p-chloro benzene under moisture free condition at an elevated temperature in the range of 50 to 200°C. In the reaction a condensing agent can be used as required from acetic anhydride, trifluoroacetic anhydride, EDCI hydrochloride, p-toluenesulfonic acid, acetic acid, and polyphosphoric acid. The compound of present invention (II) can also be produced in one step by reacting (III) and (IV) in presence of condensing agent as described in previous process without isolating the intermediate (V) and further condensing directly to get the compound of present invention (II) as described above.

[0121] Process 2:

[0122] Compounds of formula (II), corresponding to compounds of formula (I) may be prepared by reaction of compounds of formula (III) with compounds of formula (VI) as displayed under Process 2.

[0123] All variables in formulae (III), (VI), (VII) and (II) have a meaning as defined for formula (I). Reactions of this type have been described in WO 2014132971.

[0124] The intermediate (VII) is prepared by reacting (III) and (VI) at temperatures in the range of 0 to 120°C in an inert solvent in the presence of bases such as pyrrolidine; tertiary amines, such as diisopropylethylamine, trimethylamine, triethylamine, triisopropylamine and N-methylpiperidine, imidazole, pyridine; substituted pyridines, such as collidine, lutidine and 4- dimethylaminopyridine, and polycyclic amides and amidines, such as 1 ,8-diazabicycloundec-7- ene (DBU), 1 ,4-Diazabicyclo[2.2.2]octane (DABCO) etc. in suitable solvents are aliphatic hydrocarbons, such as pentane, hexane, cyclohexane, or petrol ether; aromatic hydrocarbons, such as benzene, toluene, o-, m-, and p-xylene; halogenated hydrocarbons, or halogenated aromatic Ce-Cw-hydrocarbons, such as CH2CI2, CHCI3, CCI4, CH2CICH2CI, CCI3CH3, CHCI2CH2CI, CCI2CCI2, or chlorobenzene; ethers, such as CH3CH2OCH2CH3, (CH3)2CHOCH(CH3)2, CH3OC(CH3)3(MTBE), CH3OCH3 (DME), CH3OCH2CH2OCH3, CH3OC(CH3)2CH2CH3, dioxane, anisole, 2-methyltetrahydrofuran, tetrahydrofuran (THF), and diethylene glycol; nitriles, such as CH3CN, and CH3CH2CN. The compound of present invention (II) can be produced by intramolecular condensation of intermediate (VII). The reaction is carried out in an organic solvent such as benzene, toluene, o-, m-, and p-xylene; halogenated BASF SE 240867W001

[0125] B19464WO 14 hydrocarbons, or halogenated aromatic Ce-Cw-hydrocarbons, CH3CH2CH2OH, CH3CH(OH)CH3, CH3(CH2)3OH, and C(CH3)3OH, CH2(OH)CH2(OH), and CH3CH(OH)CH2OH, o-, m-, and p- chloro benzene under moisture free condition at an elevated temperature in the range of 50 to 200°C. In the reaction a condensing agent can be used as required from acetic anhydride, trifluoroacetic anhydride, EDCI hydrochloride, p-toluenesulfonic acid, acetic acid, and polyphosphoric acid.

[0126] Process 3:

[0127] Compounds of formula (II), corresponding to compounds of formula (I) may be prepared by reaction of compounds of formula (III) with compounds of formula (VIII) as displayed under Process 3.

[0128] All variables in formulae (III), (VIII) and (II) have a meaning as defined for formula (I). Reactions of this type have been described in WO 2014132971 and WO 2014123205. The reaction is usually carried out in suitable solvents such as in suitable solvents are aliphatic hydrocarbons, such as pentane, hexane, cyclohexane, or petrol ether; aromatic hydrocarbons, such as benzene, toluene, o-, m-, and p-xylene; halogenated hydrocarbons, or halogenated aromatic Ce-Cw-hydrocarbons, such as CH2CI2, CHCI3, CCI4, CH2CICH2CI, CCI3CH3, CHCI2CH2CI, CCI2CCI2, or chlorobenzene; ethers, such as CH3CH2OCH2CH3, (CH3)2CHOCH(CH3)2, CH3OC(CH3)3(MTBE), CH3OCH3 (DME), CH3OCH2CH2OCH3, CH3OC(CH3)2CH2CH3, dioxane, anisole, 2-methyltetrahydrofuran, tetrahydrofuran (THF) at a temperature in the range of 0 to 120°C in presence of oxidizing agent such as oxygen, copper(ll) chloride, copper (II) triflate, Zinc Oxide, Iron Oxide, and DDQ as described in Journal of Molecular Structure (2024), 1312. The reaction can also be carried out in presence of acids such as acetic acid, trifluoroacetic acid, p-toluenesulfonic acid, and polyphosphoric acid. Also, the reaction can be carried out, in the presence of a sulfite, as necessary. Examples of the sulfite include sodium bisulfite and sodium disulfite.

[0129] Process 4:

[0130] Reaction of nitrile intermediate (IX) with III in presence of lewis acids such as Copper (II) triflate as described in Journal of Chemical Research (2012), 36(6), 370-373, cesium hydroxide as BASF SE 240867W001

[0131] B19464WO

[0132] 15 described in CN 103304507, Sodium carbonate and Zinc (II) chloride as described in CN111349048 can also provide the desired product of interest (II).

[0133] Process 5:

[0134] Intermediate (XII) can be produced by reacting intermediate (III) with acid intermediate (X) as described in process 1 or reaction between intermediate (III) and acid chloride (XI) as described in process 2. Further condensation reaction (as described in process 1 and 2) to get the key intermediate (XIV) bearing key leaving group (LG) such as -F, -Cl, -Br, -I, -NO2, -OTf, -OTs, - OMs, etc. Similarly, reaction of intermediate (III) with XII as described in process 4 also provides the intermediate XIV.

[0135] Intermediate (XV) can be obtained by the treatment of intermediate XII wherein LG can be Cl, Br, I, -OTf, or leaving group by displacement reaction nitro group (which can also be any other leaving group such as Cl, Br, I, F, -OTf, -OTs etc.) with HS-RW wherein RW is C1-C6-alkyl, C3- C6-cycloalkyl, C3-C6-cycloalkyl-C1-C4-alkyl, which groups are halogenated or non-halogenated is in presence of base e.g. potassium carbonate, sodium carbonate, cesium carbonate, sodium hydride etc in solvent like DMF, THF and DMSO at cooling to ambient temperature. Such method has been described in literature like Tetrahedron Letters, 2014, vol. 55, # 22, p. 3295 - 3298. This intermediate XIII can be further oxidized to achieve the final compound (II) by oxidation reaction of the corresponding sulfide intermediate, involving reagents such as, m- chloroperoxybenzoic acid, hydrogen peroxide, oxone, sodium periodate, sodium hypochlorite or BASF SE 240867W001

[0136] B19464WO

[0137] 16 tert-butyl hypochlorite and the solvents used for the oxidations include aliphatic halogenated hydrocarbons such as dichloromethane and chloroform; alcohols such as methanol and ethanol; acetic acid; water. The amount of the oxidant to be used in the reaction is generally 1 to 3 moles, preferably 1 to 1.2 moles, relative to 1 mole of the sulfide compounds VII to produce the sulfoxide compounds, and preferably 2 to 2.2 moles of oxidant, relative to 1 mole of the sulfide compounds XIII as descried in WO 2015 / 091945 Al, WO 2016107742 and WO

[0138] 2018095795. Furthermore, reaction of intermediate (XIV) directly with Sodium alkylsulfinate under heating condition in presence of base as described in process 1 or without base at temperature ranging from 50-150°C gives desired compound of II.

[0139] Process 6:

[0140] Intermediate (XVIII) can be prepared by condensation of intermediate (XVI) with III as described in process 3 and / or condensation of intermediate (XVII) with III as described in process 4.

[0141] Furthermore, intermediate XIX can be prepared by the reaction as described in process 5. Also, further oxidation results in final compound II.

[0142]

[0143] Intermediate XXIV can be obtained by the reaction of intermediate III with (XX) wherein X can be Cl, Br, I, -OTf, or leaving group as described in process 1.

[0144] Intermediate XXIV can be obtained by the reaction of intermediate III with (XXI) wherein X can be Cl, Br, I, -OTf, or leaving group as described in process 2.

[0145] Intermediate XXIV can be obtained by the reaction of intermediate III with (XXII) wherein X can be Cl, Br, I, -OTf, or leaving group as described in process 3. Intermediate XXIV can be obtained by the reaction of intermediate III with (XXIII) wherein X can be Cl, Br, I, -OTf, or leaving group as described in process 4.

[0146] Furthermore, intermediate XXVI and XXV can be prepared from the intermediate (XXIV) as described in process 5.

[0147] Compounds of formula (II) can be prepared by reacting compound XXVI in which X is a leaving group such as, for example, chlorine, bromine or iodine (preferably bromine), or an aryl-, alkyl- or haloalkylsulfonate such as trifluoromethanesulfonate, with a reagent R3-B(OH)2 (XXVII), R3- BASF SE 240867W001

[0148] B19464WO

[0149] 18

[0150] B(OR2) (XXVIII) where R could be alkyl, aryl, cycloalkyl or pinacole type of cyclic groups of the formula, wherein R3 is as defined in formula I. The reaction may be catalyzed by a palladium based catalyst, involving for example bis(diphenylphosphino)ferrocene]dichloropalladium (ll)(1 :1) (Pd(dppf)CI2). DCM complex, , tetrakis(triphenylphosphine)palladium(0) , bis(dibenzylideneacetone)palladium(O) (Pd(dba)2), tris(dibenzylideneacetone)dipalladium(0) (Pd2(dba)3; optionally in form of its chloroform adduct) or palladium(ll) acetate, and a ligand, for example XantPhos ((5-diphenylphosphanyl-9,9-dimethyl-xanthen-4-yl)diphenylphosphane), RuPhos (2-dicyclohexylphosphino2',6'-diisopropoxybiphenyl), JohnPhos ([1,1 -biphenyl]-2- ylbis(1 ,1 -dimethyl-ethyl)phosphine), BINAP (2,2'-bis(diphenylphosphino)-1 ,1'-binaphthalene), tol-BINAP ([2,2'-bis(di-p-tolyl-phosphino)- 1,1'- binaphthyl]) or tri-(o-tolyl)phosphine, in presence of a base, like sodium, potassium or cesium carbonate, or sodium or potassium tert-butylate, in a solvent or a solvent mixture, like, for example dioxane, 1,2-dimethoxyethane or toluene, preferably under inert atmosphere. The reaction temperature can preferentially range from room temperature to the boiling point of the reaction mixture, or the reaction may be performed under microwave irradiation. Such reactions have been described, for example, in Molecules 2012, 17, 4508-4521 , Advanced Synthesis & Catalysis (2015), 357(2-3), 361-365, WO2022025242 A1, Org. Lett., 2001, 3, 2757-2759 or Synlett, 2009, 1761-1764. The reaction temperature can preferentially range from room temperature to the boiling point of the reaction mixture, or the reaction may be performed under microwave irradiation. Such reactions have been described, for example, in Advanced Synthesis & Catalysis, 350(3), 391-394; 2008.

[0151] BASF SE 240867W001

[0152] B19464WO 19

[0153] Process 8a:

[0154] BASF SE 240867W001

[0155] B19464WO

[0156] Compounds of formula (XXIX) can be purchased commercially. Accordingly, compounds of formula (VI), (VI), (VIII), (XXXVI), (XXXV) wherein all variables have a definition as in formula (I), may for example be prepared as follows.

[0157] Intermediate XXX can be obtained by the treatment of intermediate XXIX wherein X can be Cl, Br, I, -OTf, or leaving group by displacement reaction of nitro group (which can also be any other leaving group such as Cl, Br, I, F, -OTf, -OTs etc.) with HS-RW wherein Rwis Ci-Ce-alkyl, Cs-Ce-cycloalkyl, C3-C6-cycloalkyl-Ci-C4-alkyl, which groups are halogenated or nonhalogenated is in presence of base e.g. potassium carbonate, sodium carbonate, cesium carbonate, sodium hydride etc. in solvent like DMF, THF and DMSO at cooling to ambient temperature. Such method has been described in literature like Tetrahedron Letters, 2014, vol. 55, # 22, p. 3295 - 3298. Intermediate XXIX can be oxidized to SO (sulfoxide) and / or SO2 (sulfone), by oxidation reaction of the corresponding sulfide intermediate, involving reagents such as, m-chloroperoxybenzoic acid, hydrogen peroxide, oxone, sodium periodate, sodium hypochlorite or tert-butyl hypochlorite and the solvents used for the oxidations include aliphatic halogenated hydrocarbons such as dichloromethane and chloroform; alcohols such as methanol and ethanol; acetic acid; water. The amount of the oxidant to be used in the reaction is generally 1 to 3 moles, preferably 1 to 1.2 moles, relative to 1 mole of the sulfide compounds XXIX to produce the sulfoxide compounds, and preferably 2 to 2.2 moles of oxidant, relative to 1 mole of the sulfide compounds XXIX as described in WO 2015 / 091945 Al, WO 2016107742 and WO 2018095795. Hydrolysis of compounds of formula (XXXI), as defined in formula I, and in which X is a leaving group, in particular those compounds wherein X is a halogen (even more preferably chlorine, bromine or iodine), for example through heating (XXXI) in concentrated acid, such as concentrated hydrochloric acid HOI cone, or sulfuric acid H2SO4 cone., preferably in the presence of water, optionally in the presence of an inert solvent, such as acetic acid or ethers (for example tetrahydrofuran, ethylene glycol dimethyl ether or 1,4-dioxane) gave XXXII. Such hydrolysis conditions, and variants thereof, are known to a skilled person. Suzuki coupling BASF SE 240867W001

[0158] B19464WO

[0159] 21

[0160] (as described in process 7) can be used to generate compound IV, which have a meaning as defined for formula (I), was reacted with compound III to generate (II) by direct condensation reaction or via intermediate by amide formation reaction followed by condensation reaction. Intermediate (IV) and (XXXII) can be further converted to corresponding acid chlorides (VI) and (XXXVI) respectively using thionyl chloride, oxalyl chloride, or the person with knowledge of chemistry can perform this organic transformation. These acid chloride intermediates can be further reacted with intermediate (III) to generate compound of formula (II) in one step by condensation reaction or by amide formation reaction as described in process 2. Similarly, first a Suzuki coupling reaction can be performed as described above to convert intermediate (XXIX) to the (XXXIII). Followed by sequence of SNAr displacement reaction to get the intermediate (XXXIV) as described above. Oxidation of (XXXIV) to (IX) using the oxidation protocol followed by acid hydrolysis to get the intermediate (IV). Intermediate (VII) and (XXXV) can be achieved by reduction reaction of nitrile intermediate (IX) and (XXXI) using DI BAL. These intermediates further reacted with (III) under oxidative reaction conditions to get the compound of formula (II).

[0161] Process 9:

[0162] XXXVII XXXVIII111

[0163] The intermediate compound (XXXVIII) can either be purchased or produced by reacting the intermediate (XXXVII) under nitration reaction condition. The reaction condition includes concentrated nitric acid in presence or absence of sulfuric acid, acetic acid. The reaction can also be carried out in presence of NaNCh, KNO2 in concentrated sulfuric acid. The reaction is usually carried out in a solvent, such as dichloromethane and chloroform, acetic acid, concentrated sulfuric acid, concentrated nitric acid, water, and mixtures thereof. In the reaction, the nitrating agent is usually used in a ratio of 1 to 3 mol, based on 1 mol of the intermediate compound (XXXVII). The reaction temperature is usually within the range of -10 to 100°C. The reaction time is usually within the range of 0.1 to 24 hours.

[0164] The intermediate compound (III) can be produced by reacting the intermediate compound (XXXVIII) with hydrogen, in the presence of a hydrogenation catalyst condition. The transition metal compounds such as palladium carbon, palladium hydroxide, Raney nickel, and platinum oxide can be used for the hydrogenation reaction in presence of Hydrogen. The reaction is usually carried out in THF, ethylene glycol dimethyl ether, tert-butyl methyl ether and 1 , 4- dioxane, esters such as ethyl acetate and butyl acetate, alcohols such as methanol and ethanol, water, and mixtures thereof a in a hydrogen atmosphere of 1 to 100 atmospheric pressure. The reaction temperature is usually within the range of -20 to 100°C. The reaction time is usually within the range of 0.1 to 24 hours. BASF SE 240867W001 B19464WO 22

[0165] Process 10:

[0166] XXXIX

[0167] Process 1

[0168] Process 2

[0169] Process 3

[0170] Process 4

[0171] Accordingly, compounds of formula (XLIV), and (XLII), wherein all variables have a definition as in formula (I), may for example be prepared as follows. Compound (XXXIX) can either be purchased or synthesized as described in process 9. Reaction of (XXXIX) with corresponding condensing partner as described in process 1 to 4 to provides intermediate (XL). Further oxidation of (XL) as described in process 5 at 0°C gives sulfoxide intermediate (XLI), which upon further coupling reaction as described in process 7 gives compound (XLII), where in all the variables have a definition as in formula (I). Similarly, complete oxidation of (XL) as described in process 5 at 25 to 100°C gives sulfone intermediate (XLIII), which upon further coupling reaction as described in process 7 gives compound (XLII), where in all the variables have a definition as in formula (I). BASF SE 240867W001

[0172] B19464WO

[0173] Process 11 :

[0174] In another method, a compound of formula (XLVI) wherein all variables have a definition as in formula (I), may for example be prepared as follows. Intermediate (XXXIX) can be reacted with triethyl orthoformate, carbon monoxide, in presence of oxygen, zinc oxide, acids such as sulfuric acid, acetic acid at a temperature ranging from 25 to 150°C to generate intermediate (XLV). Furthermore, metal catalyzed C-H bond activation reaction coupling reactions to get the compound (XLVI). The reaction may be catalyzed by a palladium based catalyst, involving for example bis(diphenylphosphino)ferrocene]dichloropalladium (ll)(1 :1) (Pd(dppf)Ch). DCM complex, , tetrakis(triphenylphosphine)palladium(0) , bis(dibenzylideneacetone)palladium(O) (Pd(dba)2), tris(dibenzylideneacetone)dipalladium(0) (Pd2(dba)s; optionally in form of its chloroform adduct) or palladium(ll) acetate, and a ligand, for example XantPhos ((5- diphenylphosphanyl-9,9-dimethyl-xanthen-4-yl)diphenylphosphane), RuPhos (2- dicyclohexylphosphino2',6'-diisopropoxybiphenyl), JohnPhos ([1 ,1 -biphenyl]-2-ylbis(1 , 1 - dimethyl-ethyl)phosphine), BINAP (2,2'-bis(diphenylphosphino)-1 ,1'-binaphthalene), tol-BINAP ([2,2'-bis(di-p-tolyl-phosphino)- 1,1'- binaphthyl]) or tri-(o-tolyl)phosphine, in presence of a base, like sodium, potassium or cesium carbonate, or sodium or potassium tert-butylate, in a solvent or a solvent mixture, like, for example dioxane, 1,2-dimethoxyethane or toluene, preferably under inert atmosphere. The reaction can also be performed using copper iodide, copper chloride, Dichlorobis(pyridine)nickel,1 H-lmidazolium, 1,3-bis(2,4,6-trimethylphenyl)-, chloride (1 :1). The reaction temperature can preferentially range from room temperature to the boiling point of the reaction mixture. Such reactions have been described in Chemistry - A European Journal (2023), 29(44), e202301310, European Journal of Inorganic Chemistry (2023), 26(22), e202300126, ChemCatChem (2022), 14(24), e202201055, Science Bulletin (2022), 67(1), 71- 78 etc.

[0175] Process 12:

[0176] In another method, a compound of formula (XLVI) weheren in wherein all variables have a definition as in formula (I), may for example be prepared as follows. Intermediate (XLVII) can be reacted with m-chloroperbenzoic acid (mCPBA) in chlorinated solvents (DCM or DCE) to afford the corresponding pyridine N-oxide species. Further treatment of such N-oxide with phosphoryl trihalide (LG = Cl, Br) in neat or in aprotic solvent like toluene to generate a corresponding 6- halo intermediate (XLVIII), which upon further coupling reaction as described in process 7 gives BASF SE 240867W001

[0177] B19464WO

[0178] 24 compound (XLVI), where in all the variables have a definition as in formula (I). Such reactions have been described in W02015002211 or JP4406155.

[0179] The reaction mixtures are worked up in a customary manner, for example by mixing with water, separating the phases and, if appropriate, chromatographic purification of the crude products. Some of the intermediates and end products are obtained in the form of colorless or slightly brownish viscous oils which are purified or freed from volatile components under reduced pressure and at moderately elevated temperature. If the intermediates and end products are obtained as solids, purification can also be carried out by recrystallization or digestion.

[0180] The N-oxides may be prepared from the inventive compounds according to conventional oxidation methods, e. g. by treating compounds I with an organic peracid such as metachloroperbenzoic acid (cf. WO 03 / 64572 or J. Med. Chem. 38(11), 1892-903, 1995); or with inorganic oxidizing agents such as hydrogen peroxide (cf. J. Heterocyc. Chem. 18(7), 1305-8, 1981) or oxone (cf. J. Am. Chem. Soc. 123(25), 5962-5973, 2001). The oxidation may lead to pure mono-N-oxides or to a mixture of different N-oxides, which can be separated by conventional methods such as chromatography.

[0181] If the synthesis yields mixtures of isomers, a separation is generally not necessarily required since in some cases the individual isomers can be interconverted during work-up for use or during application (for example under the action of light, acids or bases). Such conversions may also take place after use, for example in the treatment of plants in the treated plant, or in the harmful fungus to be controlled.

[0182] A skilled person will readily understand that the preferences for the variables defined herein, also in particular the ones given in the tables below for the respective substituents, given herein in connection with compounds I apply for the intermediates (compounds II to XLVIl) accordingly. Thereby, the substituents in each case have independently of each other or more preferably in combination the meanings as defined herein.

[0183] The variables have, each on their own and in combination, the following preferred meanings. In a certain aspect, the invention relates to a compound of formula (I), wherein

[0184] R1is S(O)m-Ci-C4-alkyl, S(O)m-C3-C6-cycloalkyl, S(O)m-C3-C6-cycloalkyl-Ci-C4-alkyl, which are unsubstituted or halogenated; S(O)(=NH)RM, S(O)(=NRM)RM;

[0185] Rwis Ci-C4-alkyl, cyclopropyl, C3-C6-cycloalkyl-Ci-C4-alkyl; m is 0, 1 or 2; n is 0, 1 or 2;

[0186] R2is Ci-C4-alkyl, Ci-C4-alkoxy, Cs-Ce-cycloalkyl, halogen, cyano, NHRM, N(RM)2, NH-CO- RM, CO-NH2, CO-NHRM, CO-N(RM)2; or phenyl which is unsubstituted or substituted with at least one Ci-C4-alkyl which is unsubstituted or partially or fully halogenated; Cs-Ce-cycloalkyl, halogen, O-S(O)2-RM, BASF SE 240867W001

[0187] B19464WO 25

[0188] CN, Ci-Cs-alkoxy, which is unsubstituted or partially or fully halogenated, C3-C6- cycloalkoxy; N=S(O)(RM)2or a five- or six-membered heterocycle, which is saturated, partially unsaturated, or fully unsaturated, and which is unsubstituted or substituted with at least one halogen, CN, Ci-C4-alkyl which is unsubstituted or partially or fully halogenated; C3-C6- cycloalkyl, Ci-Cs-alkoxy, which is unsubstituted or partially or fully halogenated;

[0189] R3is

[0190] (1) Cs-Ce-cycloalkyl, which is unsubstituted or partially or fully halogenated; or halogen;

[0191] (2) phenyl substituted with (a) one R4, or (b) substituted with one R4and one halogen, or (c) substituted with up to 5 halogens;

[0192] (3) 1 ,3-benzodioxole which is unsubstituted or partly or fully halogenated;

[0193] (4) a six-membered saturated, partially unsaturated, or fully unsaturated heterocyclic ring or ring system, wherein said heterocyclic ring or ring system comprises one, two or three, same or different heteroatoms O or N which may be unsubstituted or substituted with Ci-C4-alkyl, and is unsubstituted, or substituted with one R4, or substituted with two halogens;

[0194] (5) or Ci-C4-alkynyl, which is unsubstituted or substituted with Cs-Ce-cycloalkyl or Si(R5)3; wherein R5is Ci-C4-alkyl; or

[0195] (6) a five-membered saturated, partially unsaturated, or fully unsaturated heterocyclic ring, wherein said heterocyclic ring comprises one, two or three, same or different heteroatoms selected from N, O, and S, wherein N may be unsubstituted or substituted with Ci-C4-alkyl, Cs-Ce-cycloalkyl, C-bound Ci-C4-alkoxy, Ci-C4-alkyl-Ci-C4-alkoxy; wherein the five-membered ring is unsubstituted or substituted with one R4;

[0196] R4is halogen, cyano, Ci-C4-alkyl, which is unsubstituted or partially or fully halogenated;

[0197] NH-CO-RM;

[0198] Cs-Ce-cycloalkyl;

[0199] Ci-C4-alkoxy-Ci-C4-alkyl, Cs-Ce-cycloalkyl-Ci-Cs-alkoxy, Ci-C4-alkoxy-Ci-C4-alkoxy-Ci- C4-alkyl;

[0200] C(RM)2-CN, CHRM-CN, C(RM)2-(CONH2), CHRM-(CONH2), C(RM)2-(CSNH2), CHRM- (CSNH2), l-cyano-Cs-Ce-cycloalkyl, l-Cs-Ce-cycloalkyl-carboxamide, I-C3-C6- cycloalkyl-thiocarboxamide,

[0201] O-CH2-CN, O-CHRM-CN, O-C(RM)2-CN, O-C(RM)2-(CONH2), O-C(RM)2-(CSNH2), O-l-cyano-Cs-Ce-cycloalkyl, O-C(CONH2)-C3-C6-cycloalkyl, O-C(CSNH2)-C3-C6- cycloalkyl;

[0202] O-S(O)2-RM;

[0203] Ci-Cs-alkoxy, which is unsubstituted or partially or fully halogenated; Cs-Ce-cycloalkyl- Ci-Cs-alkoxy which is unsubstituted or partially or fully halogenated, Cs-Ce-cycloalkoxy, which is unsubstituted or partially or fully halogenated;

[0204] S-RM, SO-RM; SO2-RM;S(O)(=NRM)RM, S(O)(=NH)RM,

[0205] N=S(O)(RM)2, CO-N=SO(RM)2,

[0206] SF5, (=O), C(=O)H, C(=O)RM, difluoromethylen, each RMis independently Ci-Cs-alkyl which is unsubstituted or partially or fully halogenated; or Cs-Ce-cycloalkyl, or Cs-Ce-cycloalkyl in which at least one C is replaced by a heteroatom; BASF SE 240867W001

[0207] B19464WO

[0208] 26 or in case of two adjacent substituents RM, the substituents may form a ring together by a C2-Ce-alkyl bridge, which is unsubstituted or partly or fully halogenated and in which one or more carbon atoms may be replaced by O or N; and the N-oxides, stereoisomers, tautomers and agriculturally or veterinarily acceptable salts thereof.

[0209] In one embodiment of the invention, R1is S(O)m-Ci-C4-alkyl, S(O)m-C3-C6-cycloalkyl, S(O)m-C3- C6-cycloalkyl-Ci-C4-alkyl, which are unsubstituted or halogenated, preferably halogenated; S(O)(=NH)RM, S(O)(=NRM)RM.

[0210] In another embodiment of the invention, R1is S(O)m-Ci-C4-alkyl, which are halogenated, S(O)(=NH)RMor S(O)(=NRM)RM

[0211] In the embodiments of the invention, m is 0, 1 or 2, preferably 1.

[0212] In another embodiment of the invention, R1is (S=O)-CF3, SO2-CF3, SCF3, S(O)(=NH)CF3 or S(O)(=NCH3)CF3.

[0213] In one embodiment of the invention, R1is S(O)m-Ci-C4-alkyl, S(O)m-C3-C6-cycloalkyl, S(O)m-C3- C6-cycloalkyl-Ci-C4-alkyl, which are unsubstituted or halogenated, preferably halogenated; In another embodiment of the invention, R1is (S=O)-CF3, SO2-CF3, SCF3. In another embodiment of the invention, R1is (S=O)-CF3.

[0214] In another embodiment of the invention, R1is S(O)(=NH)RMor S(O)(=NRM)RM, wherein RMis each independently Ci-Cs-alkyl which is unsubstituted or partially or fully halogenated. In another embodiment of the invention, R1is S(O)(=NH)CF3 or S(O)(=NCH3)CF3.

[0215] In one embodiment of the invention, R1is Ci-C4-alkyl, Cs-Ce-cycloalkyl, Ci-C4-alkoxy, -O-C3-C6- cycloalkyl, all of which are unsubstituted, partially halogenated or fully halogenated.

[0216] In one embodiment of the invention, Rwis Ci-C4-alkyl, cyclopropyl, C3-C6-cycloalkyl-Ci-C4-alkyl, and n is 0, 1 , or 2, preferably 2.

[0217] In another embodiment of the invention, Rwis Ci-C4-alkyl and n is 0, 1 , or 2, preferably 2. In another embodiment of the invention, Rwis methyl, ethyl or isopropyl and n is 0, 1 , or 2, preferably 2. In another embodiment of the invention, Rwis ethyl and n is 2.

[0218] In one embodiment of the invention, R1is (S=O)-CF3, SO2-CF3, SCF3, S(O)(=NH)CF3 or S(O)(=NCH3)CF3, and Rwis ethyl and n is 2.

[0219] In one embodiment of the invention, R1is (S=O)-CF3, SO2-CF3, SCF3, and Rwis ethyl, n is 2.

[0220] In one embodiment of the invention, R1is S(O)(=NH)RMor S(O)(=NRM)RM, wherein RMis each independently Ci-Cs-alkyl which is unsubstituted or partially or fully halogenated, and Rwis ethyl, n is 2. In another embodiment of the invention, R1is S(O)(=NH)CF3 or S(O)(=NCH3)CF3, and Rwis ethyl and n is 2.

[0221] In one embodiment of the invention, R1is Ci-C4-alkyl, Cs-Ce-cycloalkyl, Ci-C4-alkoxy, -O-C3-C6- cycloalkyl, all of which are unsubstituted, partially halogenated or fully halogenated, and Rwis ethyl, n is 2. In one embodiment of the invention, R1is methyl, ethyl, cyclopropyl, methoxy or trifluoromethoxy, and Rwis ethyl, n is 2.

[0222] In one embodiment of the invention, R2is Ci-C4-alkyl, Ci-C4-alkoxy, Cs-Ce-cycloalkyl, halogen, cyano, NHRM, N(RM)2, NH-CO-RM, CO-NH2, CO-NHRM, CO-N(RM)2; or Ci-C4-alkynyl. In one BASF SE 240867W001

[0223] B19464WO

[0224] 27 embodiment of the invention, R2is methyl, methoxy, cyclopropyl, ethynyl, chloro, cyano, dimethylamino, acetamino (NH-CO-CH3); CONH2, methylamino.

[0225] In one embodiment of the invention, R2is Ci-C4-alkyl. In one embodiment of the invention, R2is methyl.

[0226] In one embodiment of the invention, R2is methoxy. In one embodiment of the invention, R2is cyclopropyl. In one embodiment of the invention, R2is ethynyl. In one embodiment of the invention, R2is chloro. In one embodiment of the invention, R2is cyano. In one embodiment of the invention, R2is dimethylamino. In one embodiment of the invention, R2is acetamino.

[0227] In one embodiment of the invention, R2is phenyl which is unsubstituted or substituted with at least one Ci-C4-alkyl which is unsubstituted or partially or fully halogenated; Cs-Ce-cycloalkyl, halogen, O-S(O)2-RM, CN, Ci-Cs-alkoxy, which is unsubstituted or partially or fully halogenated,

[0228] Cs-Ce-cycloalkoxy, N=S(O)(RM)2. In one embodiment of the invention, R2is phenyl substituted with O-S(O)2-RM, in particular O-S(O)2-C

[0229] In one embodiment of the invention, R2is:

[0230] In one embodiment of the invention, R2is a five- or six-membered heterocycle, which is saturated, partially unsaturated, or fully unsaturated, for example aromatic, and which is unsubstituted or substituted with at least one halogen, CN, Ci-C4-alkyl which is unsubstituted or partially or fully halogenated; Cs-Ce-cycloalkyl, Ci-Cs-alkoxy, which is unsubstituted or partially or fully halogenated. In one embodiment of the invention, R2is a five-membered aromatic or non-aromatic heterocycle, which is unsubstituted or substituted with at least one halogen or C3- Ce-cycloalkyl, in particular with one chloro, bromo or cyclopropyl. In one embodiment of the invention, R2is pyrazole, triazole, imidazole or thiazole, which is unsubstituted or substituted with at least one halogen or Cs-Ce-cycloalkyl, in particular with one chloro, bromo or cyclopropyl. In one embodiment of the invention, the heterocyclic ring is bound to the remainder of the molecule via a nitrogen atom (N-linked). In another embodiment of the invention, the heterocyclic ring is bound to the remainder of the molecule via a carbon atom in the ring (C- linked).

[0231] In one embodiment of the invention, R2is selected from the following:

[0232] In one embodiment of the invention, R2is a six-membered aromatic or non-aromatic heterocycle, which is unsubstituted or substituted with at least one halogen or CN. In one embodiment of the invention, R2is pyridine, substituted with at least one halogen or CN. In one embodiment of the invention, R2is selected from the following: BASF SE 240867W001

[0233] B19464WO

[0234] 28

[0235] In embodiment 1 of the invention, R3is Cs-Ce-cycloalkyl, which is unsubstituted or partially or fully halogenated, or halogen. In one embodiment, R3is Cs-Ce-cycloalkyl, which is unsubstituted or partially or fully halogenated, in particular cyclopropyl.

[0236] In one embodiment, R3is halogen, in particular chloro or bromo. In one embodiment, R3is bromo.

[0237] In embodiment 2 of the invention, R3is phenyl substituted with (a) one R4, or (b) substituted with one R4and one halogen, or (c) substituted with up to 5 halogens;. In one embodiment of the invention, R3is phenyl substituted with one R4, or substituted with 2 or 3 halogens.

[0238] In one embodiment of the invention, the compound of formula (I) is the compound I. A:

[0239] In one embodiment of the invention, R3is phenyl substituted with one R4and one fluoro atom.

[0240] In one embodiment of the invention, the compound of formula (I) is the compound I.A-b:

[0241] In one embodiment of the invention, the compound of formula (I) is the compound I. A’ or I. A”

[0242] In one embodiment, R3is 2,4-difluorophenyl.

[0243] In embodiment 3 of the invention, R3is 1 ,3-benzodioxole which is unsubstituted or partly or fully halogenated. In a particular embodiment, R3is difluorobenzodioxole:

[0244] In embodiment 4 of the invention, R3is a six-membered saturated, partially unsaturated, or fully unsaturated heterocyclic ring or ring system, wherein said heterocyclic ring or ring system BASF SE 240867W001

[0245] B19464WO comprises one, two or three, same or different heteroatoms O or N which may be unsubstituted or substituted with Ci-C4-alkyl, and is unsubstituted, or substituted with one R4, or substituted with two halogens.

[0246] In one embodiment of the invention, the compound I is compound I*: wherein

[0247] X is C, O;

[0248] Y is C, N;

[0249] Z is C, N, O;

[0250] M is C, N;

[0251] A is C.

[0252] In one embodiment of the invention, R3is one of the following heterocycles

[0253] In one embodiment of the invention, R3is one of the heterocycles R3.6.1 to R3.6.12.

[0254] In one embodiment of the invention, R3is one of the heterocycles R3.6.1 to R3.6.5.

[0255] In one embodiment of the invention, R3is one of the heterocycles R3.6.4 or R3.6.5, in particular

[0256] R3.6.4

[0257] In one embodiment of the invention, R3is one of the pyrimidines R3.6.7 to R3.6.11.

[0258] In one embodiment of the invention, R3is R3.6.1 , R3.6.2 or R3.6.3, preferably R3.6.1 or R.3.2.

[0259] In one embodiment of the invention, R3is pyridyl substituted with one R4.

[0260] In embodiment 5 of the invention, R3is Ci-C4-alkynyl, which is unsubstituted or substituted with Cs-Ce-cycloalkyl or Si(R5)3; wherein R5is Ci-C4-alkyl. In a particular embodiment, R3is propargyl which is unsubstituted or substituted with Si(R5)3; wherein R5is Ci-C4-alkyl. In a particular BASF SE 240867W001

[0261] B19464WO

[0262] 30 embodiment, R3is propargyl which is unsubstituted or substituted with SiMea. In another embodiment, R3is propargyl which is substituted with cyclopropyl.

[0263] These compounds are useful as intermediates for preparing other compounds of the present invention, but also have pesticidal activity of their own, thus they are also useful as pesticides.

[0264] In embodiment 6 of the invention, R3is a five-membered saturated, partially unsaturated, or fully unsaturated heterocyclic ring, wherein said heterocyclic ring comprises one, two or three, same or different heteroatoms selected from N, O, and S, wherein N may be unsubstituted or substituted with Ci-C4-alkyl, Cs-Ce-cycloalkyl, C-bound Ci-C4-alkoxy, Ci-C4-alkyl-Ci-C4-alkoxy; and wherein the five-membered ring is unsubstituted or substituted with one R4.

[0265] In one embodiment, R3is a five-membered saturated, partially unsaturated, or fully unsaturated heterocyclic ring, wherein said heterocyclic ring comprises one, two or three, same or different heteroatoms selected from N, O, and S, wherein N may be unsubstituted or substituted with Ci- C4-alkyl; and wherein the five-membered ring is unsubstituted or substituted with one R4. The five-membered ring R3may be bound to the remainder of the molecule via a C atom of the ring (C-linked) or via a heteroatom of the ring, preferably a nitrogen atom N (N-linked).

[0266] In one embodiment, R3is bound via a C-atom of the ring (C-linked). In one embodiment, R3is bound via a nitrogen atom of the ring (N-linked).

[0267] In one embodiment, the five-membered ring R3comprises at least one nitrogen atom N in the ring, wherein said N may be unsubstituted or substituted with Ci-C4-alkyl, Cs-Ce-cycloalkyl, C- bound Ci-C4-alkoxy, Ci-C4-alkyl-Ci-C4-alkoxy, preferably Ci-C4-alkyl.

[0268] In one embodiment of the invention, the five-membered ring R3is unsubstituted.

[0269] In one embodiment of the invention, the five-membered ring R3comprises an N-atom which is unsubstituted, and wherein the ring is unsubstituted in total. In another embodiment of the invention, the five-membered ring R3comprises an N-atom which is unsubstituted, and wherein the ring is substituted with one R4.

[0270] In one embodiment of the invention, the five-membered ring R3comprises an N-atom which is substituted with Ci-C4-alkyl, Cs-Ce-cycloalkyl, C-bound Ci-C4-alkoxy, Ci-C4-alkyl-Ci-C4-alkoxy, preferably Ci-C4-alkyl, and wherein the ring is unsubstituted apart from that. In another embodiment of the invention, the five-membered ring R3comprises an N-atom which is ssubstituted with Ci-C4-alkyl, Cs-Ce-cycloalkyl, C-bound Ci-C4-alkoxy, Ci-C4-alkyl-Ci-C4-alkoxy, preferably Ci-C4-alkyl, , and wherein the ring is substituted with one R4.

[0271] In one embodiment of the invention, the five-membered ring R3is substituted with one R4.

[0272] In one embodiment of the invention, R3is one of the following heterocycles

[0273] R3.5.1 R3.5.2 R3.5.3 R3.5.4 R3.5.5 BASF SE 240867W001

[0274] B19464WO

[0275] In one embodiment of the invention, R3is a pyrazole R3.5.1 , R3.5.2 or R3.5.3.

[0276] In one embodiment of the invention, R3is an isoxazole R3.5.4 or R3.5.5 or dihydroisoxazole R3.5.6 or R3.5.7. In one embodiment of the invention, R3is an isoxazole R3.5.4 or R3.5.5.

[0277] In one embodiment of the invention, R3is a thiazole R3.5.8, R3.5.9 or R3.5.10.

[0278] In one embodiment of the invention, R3is a triazole R3.5.11 or R3.5.12.

[0279] In one embodiment of the invention, R3is an oxadiazole R3.5.13, R3.5.14 or a thiadiazole R3.5.15.

[0280] In one embodiment of the invention, R4is halogen, cyano, Ci-C4-alkyl, which is unsubstituted or partially or fully halogenated; NH-CO-RM; Cs-Ce-cycloalkyl;

[0281] Ci-C4-alkoxy-Ci-C4-alkyl, Cs-Ce-cycloalkyl-Ci-Cs-alkoxy, Ci-C4-alkoxy-Ci-C4-alkoxy-Ci-C4-alkyl; C(RM)2-CN, CHRM-CN, C(RM)2-(CONH2), CHRM-(CONH2), C(RM)2-(CSNH2), CHRM-(CSNH2), 1- cyano-Cs-Ce-cycloalkyl, l-Cs-Ce-cycloalkyl-carboxamide, l-Cs-Ce-cycloalkyl-thiocarboxamide, O-CH2-CN, O-CHRM-CN, O-C(RM)2-CN, O-C(RM)2-(CONH2), O-C(RM)2-(CSNH2),

[0282] O-l-cyano-Cs-Ce-cycloalkyl, O-C(CONH2)-C3-C6-cycloalkyl, O-C(CSNH2)-C3-C6-cycloalkyl;

[0283] O-S(O)2-RM;

[0284] Ci-Cs-alkoxy, which is unsubstituted or partially or fully halogenated; Cs-Ce-cycloalkyl-Ci-Cs- alkoxy which is unsubstituted or partially or fully halogenated, Cs-Ce-cycloalkoxy, which is unsubstituted or partially or fully halogenated;

[0285] S-RM, SO-RM; SO2-RM;S(O)(=NRM)RM, S(O)(=NH)RM,

[0286] N=S(O)(RM)2, CO-N=SO(RM)2,

[0287] SF5, (=O), C(=O)H, C(=O)RM, difluoromethylen.

[0288] It is understood that if R4is (=0), i.e. oxo, two valencies of the substituted ring atom are used. If the ring atom is a carbon atom, this means that R4can only be oxo, if the ring is not fully unsaturated.

[0289] In one embodiment of the invention, R4is halogen, in particular fluro, chloro, bromine, even more particular bromo or chloro, more particular bromo.

[0290] In one embodiment of the invention, R4is cyano.

[0291] In one embodiment of the invention, R4is Ci-Cs-alkoxy, which is unsubstituted or partially or fully halogenated. Ini particular, R4is trifluoromethoxy, difluoromethoxy, methoxy.

[0292] In one embodiment of the invention, R4is Cs-Ce-cycloalkyl, in particular cyclopropyl. BASF SE 240867W001

[0293] B19464WO

[0294] 32

[0295] In one embodiment of the invention, R4is Cs-Ce-cycloalkoxy, which is unsubstituted or partially or fully halogenated; in particular cyclopropyloxy.

[0296] In one embodiment of the invention, R4is C(RM)2-(CN), CHRM-CN, C(RM)2-(CONH2), CHRM- (CONH2), C(RM)2-(CSNH2), CHRM-(CSNH2), 1-cyano-C3-C6-cycloalkyl, 1-C3-C6-cycloalkyl- carboxamide, 1-C3-C6-cycloalkyl-thiocarboxamide.

[0297] In one embodiment of the invention, R4is C(CH3)2-(CN), C(CH3)2-(CONH2), 1-cyano- cyclopropyl, 1-cyclopropyl-carboxamide, preferably C(CH3)2-(CN) or 1-cyano-cyclopropyl. In one embodiment of the invention, R4is C(RM)2-CN, in particular C(CH3)2-(CN).

[0298] In one embodiment of the invention, R4is C(RM)2-(CONH2) or C(RM)2-(CSNH2), in particular C(CH3)2-(CONH2) or C(CH3)2-(CSNH2).

[0299] In one embodiment of the invention, R4is 1-cyano-C3-C6-cycloalkyl, in particular 1-cyano- cyclopropyl. In one embodiment of the invention, R4is 1-C3-C6-cycloalkyl-carboxamide, 1-C3-Ce- cycloalkyl-thiocarboxamide, in particular 1-cyclopropyl-carboxamide or 1 -cyclopropylthiocarboxamide.

[0300] In one embodiment of the invention, R4is O-C(RM)2-CN, O-C(RM)2-(CONH2), O-C(RM)2-(CSNH2), in particular O-C(CH3)2-CN or O-C(CH3)2-(CONH2).

[0301] In one embodiment of the invention, R4is O-1-cyano-C3-C6-cycloalkyl, O-C(CONH2)-C3-C6- cycloalkyl, O-C(CSNH2)-C3-C6-cycloalkyl, in particular 0-1 -cyano-cyclopropyl, O-C(CONH2)- cyclopropyl, O-C(CSNH2)-cyclopropyl.

[0302] In one embodiment of the invention, R4is O-S(O)2-RM; in particular O-S(O)2-CH3.

[0303] In one embodiment of the invention, R4is SF5.

[0304] In one embodiment of the invention, R4is N=S(O)(RM)2, in particular N=S(O)(CH3)2.

[0305] In one embodiment of the invention, R4is CO-N=SO(RM)2, in particular CO-N=SO(CH3)2

[0306] In one embodiment of the invention, each RMis independently Ci-Cs-alkyl which is unsubstituted or partially or fully halogenated; or Cs-Ce-cycloalkyl, or Cs-Ce-cycloalkyl in which at least one C is replaced by a heteroatom; or in case of two adjacent substituents RM, the substituents may form a ring together by a C2-Ce-alkyl bridge, which is unsubstituted or partly or fully halogenated and in which one or more carbon atoms may be replaced by O or N.

[0307] In a particular embodiment of the invention, each RMis independently methyl, trifluoromethyl or cyclopropyl.

[0308] In another particular embodiment of the invention, two adjacent substituents RMform a ring together by a C2-Ce-alkyl bridge, which is unsubstituted or partly or fully halogenated and in which one or more carbon atoms may be replaced by O or N.

[0309] Examples for such bridge substituents are shown as RM-b1 to RM-b8, without limiting to these structures:

[0310] RM-b1 RM-b2 RM-b3 RM-b4 RM-b5 RM-b6 RM-b7 RM-b8 BASF SE 240867W001

[0311] B19464WO

[0312] 33

[0313] As used herein, the term “compound(s) of the invention” or “compound(s) according to the invention” refers to the compound(s) of formula (I) as defined above, which are also referred to as “compound(s) of formula I” or “compound(s) I” or “formula I compound(s)”, and includes their salts, tautomers, stereoisomers, and N-oxides.

[0314] Mixtures

[0315] The invention also relates to a mixture of at least one compound of the invention with at least one mixing partner. Preferred are binary mixtures of one compound of the invention as component I with one mixing partner herein as component II. Preferred weight ratios for such binary mixtures are from 5000:1 to 1:5000, preferably from 1000:1 to 1 :1000, more preferably from 100:1 to 1:100, particularly from 10:1 to 1:10. In such binary mixtures, components I and II may be used in equal amounts, or an excess of component I, or an excess of component II may be used.

[0316] Mixing partners can be selected from pesticides, in particular insecticides, nematicides, and acaricides, fungicides, herbicides, plant growth regulators, fertilizers. Preferred mixing partners are insecticides, nematicides, and fungicides.

[0317] The following list M of pesticides, grouped according the Mode of Action Classification of the Insecticide Resistance Action Committee (IRAC), together with which the compounds of the invention can be used and with which potential synergistic effects might be produced, illustrates the possible combinations:

[0318] M.1 AChE inhibitors: aldicarb, alanycarb, bendiocarb, benfuracarb, butocarboxim, butoxycarboxim, carbaryl, carbofuran, carbosulfan, ethiofencarb, fenobucarb, formetanate, furathiocarb, isoprocarb, methiocarb, methomyl, metolcarb, oxamyl, pirimicarb, propoxur, thiodicarb, thiofanox, trimethacarb, XMC, xylylcarb, triazamate; acephate, azamethiphos, azinphos-ethyl, azinphosmethyl, cadusafos, chlorethoxyfos, chlorfenvinphos, chlormephos, chlorpyrifos, chlorpyrifosmethyl, coumaphos, cyanophos, demeton-S-methyl, diazinon, dichlorvos / DDVP, dicrotophos, dimethoate, dimethylvinphos, disulfoton, EPN, ethion, ethoprophos, famphur, fenamiphos, fenitrothion, fenthion, fosthiazate, heptenophos, imicyafos, isofenphos, isopropyl O-(methoxyaminothio-phosphoryl) salicylate, isoxathion, malathion, mecarbam, methamidophos, methidathion, mevinphos, monocrotophos, naled, omethoate, oxydemeton-methyl, parathion, parathion-methyl, phenthoate, phorate, phosalone, phosmet, Phosphamidon, phoxim, pirimiphos-methyl, profenofos, propetamphos, prothiofos, pyraclofos, pyridaphenthion, quinalphos, sulfotep, tebupirimfos, temephos, terbufos, tetrachlorvinphos, thiometon, triazophos, trichlorfon, vamidothion;

[0319] M.2. GABA-gated chloride channel antagonists: cyclodiene organochlorine compounds: endosulfan, chlordane; phenylpyrazoles: ethiprole, fipronil, flufiprole, pyrafluprole, pyriprole; M.3 Sodium channel modulators: pyrethroids: acrinathrin, allethrin, d-cis-trans allethrin, d-trans allethrin, bifenthrin, kappa-bifenthrin, bioallethrin, bioallethrin S-cylclopentenyl, bio-resmethrin, cycloprothrin, cyfluthrin, beta-cyfluthrin, cyhalothrin, lambda-cyhalothrin, gamma-cyhalothrin, cypermethrin, alpha-cypermethrin, beta-cypermethrin, theta-cypermethrin, zeta-cypermethrin, cyphenothrin, deltamethrin, empenthrin, esfenvalerate, etofenprox, fenpropathrin, fenvalerate, flucythrinate, flumethrin, tau-fluvalinate, halfenprox, heptafluthrin, imiprothrin, meperfluthrin.metofluthrin, momfluorothrin, epsilon-momfluorothrin, permethrin, phenothrin, prallethrin, profluthrin, pyrethrin (pyrethrum), resmethrin, silafluofen, tefluthrin, kappa-tefluthrin, BASF SE 240867W001

[0320] B19464WO

[0321] 34 tetramethylfluthrin, tetramethrin, tralomethrin, transfluthrin; sodium channel modulators, e.g.: DDT, methoxychlor;

[0322] M.4 nAChR agonists: neonicotinoids: acetamiprid, clothianidin, cycloxaprid, dinotefuran, imidacloprid, nitenpyram, thiacloprid, thiamethoxam; 4,5-dihydro-N-nitro-1-(2-oxiranylmethyl)-1 H- imidazol-2-amine, (2E-)-1-[(6-Chloropyridin-3-yl)methyl]-N'-nitro-2-pentylidenehydrazinecarbox- imidamide; 1-[(6-Chloropyridin-3-yl)methyl]-7-methyl-8-nitro-5-propoxy-1,2,3,5,6,7-hexahydro- imidazo[1,2-a]pyridine; nicotine; sulfoxaflor; flupyradifurone; triflumezopyrim, fenmezoditiaz, flupyrimin, 1-[(2-chlorothiazol-5-yl)methyl]-3-(3,5-dimethylisoxazol-4-yl)pyrido[1,2-a]pyrimidine- 2, 4-dione;

[0323] M.5 Nicotinic acetylcholine receptor allosteric activators:spinosyns, e.g. spinosad or spineto- ram;

[0324] M.6 Chloride channel activators from the class of avermectins and milbemycins, e.g. abamectin, emamectin benzoate, ivermectin, lepimectin, or milbemectin;

[0325] M.7 Juvenile hormone mimics, such as hydroprene, kino-prene, methoprene; fenoxycarb, or pyri proxyfen;

[0326] M.8 miscellaneous multi-site inhibitors: CHaBr, other alkyl halides, chloropicrin, sulfuryl fluoride, borax, tartar emetic;

[0327] M.9 Chordotonal organ TRPV channel modulators: afidopyropen, pymetrozine; pyrifluquinazon; M.10 Mite growth inhibitors: clofentezine, hexythiazox, diflovidazin, etoxazole;

[0328] M.11 Microbial disruptors of insect midgut membranes: bacillus thuringiensis, bacillus sphaericus, and insecticdal proteins they produce e.g.: bacillus thuringiensis subsp. israelensis, bacillus sphaericus, bacillus thuringiensis subsp. aizawai, bacillus thuringiensis subsp. kurstaki, bacillus thuringiensis subsp. tenebrionis, Bt crop proteins: CrylAb, CrylAc, CrylFa, Cry2Ab, mCry3A, Cry3Ab, Cry3Bb, Cry34 / 35Ab1;

[0329] M.12 Inhibitors of mitochondrial ATP synthase: diafenthiuron, organotin miticides, e.g.: azocyclotin, cyhexatin, fenbutatin oxide, propargite, tetradifon;

[0330] M.13 Uncouplers of oxidative phosphorylation via disruption of the proton gradient: chlorfenapyr, DNOC, sulfluramid;

[0331] M.14 nAChR channel blockers: nereistoxin analogues bensultap, cartap hydrochloride, thio- cyclam, thiosultap-sodium;

[0332] M.15 Inhibitors of the chitin biosynthesis type 0, e.g.: bistrifluron, chlorfluazuron, difluben-zuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, teflubenzuron, triflumuron;

[0333] M.16 Inhibitors of the chitin biosynthesis type 1: buprofezin;

[0334] M.17 Moulting disruptors: Dipteran, cyromazine;

[0335] M.18 Ecdyson receptor agonists, e.g.: methoxyfenozide, tebufenozide, halofenozide, fufeno- zide, chromafenozide;

[0336] M.19 Octopamin receptor agonists: amitraz;

[0337] M.20 Mitochondrial complex III electron transport inhibitors: hydramethylnon, acequinocyl, fluacrypyrim; bifenazate;

[0338] M.21 METI acaricides and insecticides, e.g.: fenazaquin, fenpyroximate, pyrimidifen, pyrida- ben, tebufenpyrad, tolfenpyrad, rotenone;

[0339] M.22 Voltage-dependent sodium channel blockers: indoxacarb, metaflumizone, N-(3-chloro-2- methyl-phenyl)-2-[(4-chlorophenyl)[4-[methyl(methylsulfonyl)amino]phenyl]-methylene]- BASF SE 240867W001

[0340] B19464WO

[0341] 35 hydrazinecarboxamide, N-[4-chloro-2-[[(1,1-dimethylethyl)amino]carbonyl]-6-methylphenyl]-1-(3- chloro-2-pyridinyl)-3-(fluoromethoxy)-1 H-pyrazole-5-carboxamide, 2-[2-(4-cyanophenyl)-1-[3- (trifluoromethyl)phenyl]ethylidene]-N-[4-(difluoromethoxy)phenyl]-hydrazinecarboxamide;

[0342] M.23 Inhibitors of the of acetyl CoA carboxylase, e.g.: spirodiclofen, spiromesifen, spirotetramat; spiropidion; spirobudifen, 11-(4-chloro-2,6-dimethylphenyl)-12-hydroxy-1,4-dioxa-9- azadispiro[4.2.4.2]tetradec-11-en-10-one, spidoxamat;

[0343] M.24 Mitochondrial complex IV electron transport inhibitors: e.g. aluminium phosphide, calcium phosphide, zinc phosphide, cyanide;

[0344] M.25 Mitochondrial complex II electron transport inhibitors, e.g.: cyenopyrafen, cyflumetofen, cyetpyrafen, pyflubumide;

[0345] M.28 Ryanodine receptor-modulators: chlorantraniliprole, cyantraniliprole, cyclaniliprole, flubendiamide, fluchlordiniliprole, (R)-3-chloro-N1-{2-methyl-4-[1,2,2,2-tetrafluoro-1-(trifluoro- methyl)ethyl]phenyl}-N2-(1-methyl-2-methylsulfonylethyl)phthalamid, (S)-3-chloro-N1-{2-methyl- 4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenyl}-N2-(1-methyl-2-methylsulfonylethyl)phthal- amide, methyl-2-[3,5-dibromo-2-({[3-bromo-1-(3-chlorpyridin-2-yl)-1 H-pyrazol-5-yl]carbonyl}ami- no)benzoyl]-1,2-dimethylhydrazine-carboxylate; N-[2-(5-amino-1 ,3,4-thiadiazol-2-yl)-4-chloro-6- methyl-phenyl]-3-bromo-1-(3-chloro-2-pyridinyl)-1H-pyrazole-5-carboxamide; 3-chloro-1-(3- chloro-2-pyridinyl)-N-[2,4-dichloro-6-[[(1-cyano-1-methylethyl)amino]carbonyl]phenyl]-1 H- pyrazole-5-carboxamide; tetrachlorantraniliprole; tetraniliprole; tiorantraniliprole; N-[4-chloro-2- [[(1,1-dimethylethyl)amino]carbonyl]-6-methyl-phenyl]-1-(3-chloro-2-pyridinyl)-3-(fluoromethoxy)- 1 H-pyrazole-5-carboxamide; cyhalodiamide; N-[2-(5-amino-1 ,3,4-thiadiazol-2-yl)-4-chloro-6- methylphenyl]-3-bromo-1-(3-chloro-2-pyridinyl)-1 H-pyrazole-5-carboxamide, pioxaniliprole; M.29: Chordotonal organ Modulators: flonicamid, flumetnicam;

[0346] M.30: broflanilide; fluxametamide, isocycloseram, piperflanilide;

[0347] M.33 acynonapyr;

[0348] M.IIN. Unknown mode of action: afoxolaner, azadirachtin, amidoflumet, ben-zoximate, bromopropylate, chinomethionat, cryolite, cyproflanilid, dicloromezotiaz, dicofol, dimpropyridaz, flufenerim, flometoquin, fluensulfone, fluhexafon, fluopyram, fluralaner, metaldehyde, metoxadiazone, mivorilaner, modoflaner, piperonyl butoxide, pyridalyl, tioxazafen, trifluenfuronate, umifoxolaner, 11-(4-chloro-2,6-dimethylphenyl)-12-hydroxy-1,4-dioxa-9- azadispiro[4.2.4.2]-tetradec-11-en-10-one, 3-(4’-fluoro-2,4-dimethylbiphenyl-3-yl)-4-hydroxy-8- oxa-1-azaspiro[4.5]dec-3-en-2-one, 1-[2-fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulfinyl]phe- nyl]-3-(trifluoromethyl)-1 H-1 ,2,4-triazole-5-amine, actives on basis of bacillus firmus (Votivo, I- 1582); fluazaindolizine; N-[5-[[2-bromo-6-chloro-4-[1,2,2,3,3,3-hexafluoro-1-(trifluoromethyl)-pro- pyl]phenyl]carbamoyl]-2-cyano-phenyl]-4-cyano-2-methyl-benzamide; 4-cyano-N-[2-cyano-5- [[2,6-dichloro-4-[1,2,2,3,3,3-hexafluoro-1-(trifluoromethyl)-propyl]phenyl]carbamoyl]phenyl]-2- methyl-benzamide; 4-cyano-N-[2-cyano-5-[[2,6-dichloro-4-[1,2,2,2-tetrafluoro-1-(trifluoro- methyl)ethyl]phenyl]carbamoyl]phenyl]-2-methyl-benzamide; N-[5-[[2-bromo-6-chloro-4-[1, 2,2,2- tetrafluoro-1-(trifluoromethyl)ethyl]phenyl]carbamoyl]-2-cyano-phenyl]-4-cyano-2-methyl- benzamide;

[0349] 1-[(6-chloro-3-pyridinyl)methyl]-1,2,3,5,6,7-hexahydro-5-methoxy-7-methyl-8-nitro-imidazo[1,2- a]pyridine; 1-[(6-chloropyridin-3-yl)methyl]-7-methyl-8-nitro-1,2,3,5,6,7-hexahydroimidazo[1,2- a]pyridin-5-ol; 1-[(6-chloro-3-pyridinyl)methyl]-1,2,3,5,6,7-hexahydro-5-methoxy-7-methyl-8- nitro-imidazo[1,2-a]pyridine; 2-(3-pyridinyl)-N-(2-pyrimidinylmethyl )-2H-indazole-5-carboxamide; BASF SE 240867W001

[0350] B19464WO

[0351] 36 tyclopyrazoflor; sarolaner, lotilaner; N-[4-chloro-3-[[(phenylmethyl)amino]carbonyl]phenyl]-1- methyl-3-(1 ,1 ,2,2,2-pentafluoroethyl)-4-(trifluoromethyl)-1 H-pyrazole-5-carboxamide; N-[4- chloro-3-[[(phenylmethyl)amino]carbonyl]phenyl]-1-methyl-3-(1 , 1 ,2,2, 2-pentafluoroethyl)-4- (trifluoromethyl)-1 H-pyrazole-5-carboxamide; 2-(3-ethylsulfonyl-2-pyridyl)-3-methyl-6-(tri- fluoromethyl)imidazo[4,5-b]pyridine, 2-[3-ethylsulfonyl-5-(trifluoromethyl)-2-pyridyl]-3-methyl-6- (trifluoromethyl)imidazo[4,5-b]pyridine; N-[4-chloro-3-(cyclopropylcarbamoyl)phenyl]-2-methyl-5- (1 ,1,2,2,2-pentafluoroethyl)-4-(trifluoromethyl)pyrazole-3-carboxamide, N-[4-chloro-3-[(1- cyanocyclopropyl)carbamoyl]phenyl]-2-methyl-5-(1 , 1 ,2,2, 2-pentafluoroethyl)-4-(trifluorome- thyl)pyrazole-3-carboxamide; benzpyrimoxan; tigolaner; oxazosulfyl; [(2S,3R,4R,5S,6S)-3,5- dimethoxy-6-methyl-4-propoxy-tetrahydropyran-2-yl] N-[4-[1-[4-(trifluoromethoxy)phenyl]-1 ,2,4- triazol-3-yl]phenyl]carbamate; [(2S,3R,4R,5S,6S)-3,4,5-trimethoxy-6-methyl-tetrahydropyran-2- yl] N-[4-[1-[4-(trifluoromethoxy)phenyl]-1 ,2,4-triazol-3-yl]phenyl]carbamate; [(2S,3R,4R,5S,6S)- 3,5-dimethoxy-6-methyl-4-propoxy-tetrahydropyran-2-yl] N-[4-[1 -[4-(1 , 1 ,2,2,2- pentafluoroethoxy)phenyl]-1 ,2,4-triazol-3-yl]phenyl]carbamate; [(2S,3R,4R,5S,6S)-3,4,5- trimethoxy-6-methyl-tetrahydropyran-2-yl] N-[4-[1-[4-(1 , 1 ,2,2, 2-pentafluoroethoxy)phenyl]-1, 2,4- triazol-3-yl]phenyl]carbamate; (2Z)-3-(2-isopropylphenyl)-2-[(E)-[4-[1-[4-(trifluorome- thoxy)phenyl]-1 ,2,4-triazol-3-yl]phenyl]methylenehydrazono]thiazolidin-4-one, (2Z)-3-(2- isopropylphenyl)-2-[(E)-[4-[1-[4-(1 ,1 ,2,2,2-pentafluoroethoxy)phenyl]-1,2,4-triazol-3-yl]phe- nyl]methylenehydrazono]thiazolidin-4-one, (2Z)-3-(2-isopropylphenyl)-2-[(E)-[4-[1 -[4-(1 , 1 ,2,2,2- pentafluoroethoxy)phenyl]-1 ,2,4-triazol-3-yl]phenyl]methylenehydrazono]thiazolidin-4-one; 2-(6- chloro-3-ethylsulfonyl-imidazo[1,2-a]pyridin-2-yl)-3-methyl-6-(trifluoromethyl)imidazo[4,5- b]pyridine, 2-(6-bromo-3-ethylsulfonyl-imidazo[1,2-a]pyridin-2-yl)-3-methyl-6-(trifluoro- methyl)imidazo[4,5-b]pyridine, 2-(3-ethylsulfonyl-6-iodo-imidazo[1,2-a]pyridin-2-yl)-3-methyl-6- (trifluoromethyl)imidazo[4,5-b]pyridine, 2-(7-chloro-3-ethylsulfonyl-imidazo[1,2-a]pyridin-2-yl)-3- methyl-6-(trifluoromethyl)imidazo[4,5-b]pyridine, 2-(7-chloro-3-ethylsulfonyl-imidazo[1,2-a]pyri- din-2-yl)-3-methyl-6-(trifluoromethyl)imidazo[4,5-b]pyridine, 2-(3-ethylsulfonyl-7-iodo-imida- zo[1,2-a]pyridin-2-yl)-3-methyl-6-(trifluoromethyl)imidazo[4,5-b]pyridine, 3-ethylsulfonyl-6-iodo-2- [3-methyl-6-(trifluoromethyl)imidazo[4,5-b]pyridin-2-yl]imidazo[1 ,2-a]pyridine-8-carbonitrile, 2-[3- ethylsulfonyl-8-fluoro-6-(trifluoromethyl)imidazo[1,2-a]pyridin-2-yl]-3-methyl-6-(trifluoro- methyl)imidazo[4,5-b]pyridine, 2-[3-ethylsulfonyl-7-(trifluoromethyl)imidazo[1,2-a]pyridin-2-yl]-3- methyl-6-(trifluoromethylsulfinyl)imidazo[4,5-b]pyridine, 2-[3-ethylsulfonyl-7-(trifluoromethyl)imi- dazo[1,2-a]pyridin-2-yl]-3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridine, 2-(6-bromo-3-ethyl- sulfonyl-imidazo[1,2-a]pyridin-2-yl)-6-(trifluoromethyl)pyrazolo[4,3-c]pyridine; N-[[2-fluoro-4- [(2S,3S)-2-hydroxy-3-(3,4,5-trichlorophenyl)-3-(trifluoromethyl)pyrrolidin-1-yl]phenyl]methyl]cy- clopropanecarboxamide; sulfiflumin; flupentiofenox, N-[3-chloro-1-(3-pyridyl)pyrazol-4-yl]-2-me- thylsulfonyl-propanamide, cyclobutrifluram; N-[4-chloro-3-[(1-cyanocyclopro- pyl)carbamoyl]phenyl]-2-methyl-4-methylsulfonyl-5-(1 , 1 ,2,2,2-pentafluoroethyl)pyrazole-3- carboxamide, cyproflanilide, nicofluprole; 1 ,4-dimethyl-2-[2-(pyridin-3-yl)-2h-indazol-5-yl]-1 ,2,4- triazolidine-3, 5-dione, indazapyroxamet, tiapyrachlor, N-cyclopropyl-5-[(5S)-5-(3,5-dichloro-4- fluoro-phenyl)-5-(trifluoromethyl)-4H-isoxazol-3-yl]isoquinoline-8-carboxamide, 5-[(5S)-5-(3,5- dichloro-4-fluoro-phenyl)-5-(trifluoromethyl)-4H-isoxazol-3-yl]-N-(pyrimidin-2-ylmethyl)iso- quinoline-8-carboxamide, N-[1-(2,6-difluorophenyl)pyrazol-3-yl]-2-(trifluoromethyl)benzamide, 5- ((1R,3R)-3-(3,5-Bis(trifluoromethyl)phenyl)-2,2-dichlorocyclopropane-1-carboxamido)-2-chloro- N-(3-(2,2-difluoroacetamido)-2,4-difluorophenyl)benzamide, 1-[6-(2,2-difluoro-7-methyl- BASF SE 240867W001

[0352] B19464WO

[0353] 37

[0354] [1,3]dioxolo[4,5-f]benzimidazol-6-yl)-5-ethylsulfonyl-3-pyridyl]cyclopropanecarbonitrile, 6-(5- cyclopropyl-3-ethylsulfonyl-2-pyridyl)-2,2-difluoro-7-methyl-[1,3]dioxolo[4,5-f]benzimidazole, Ledprona. Flupyroxystrobin, 3,5-bis(trifluoromethyl)-N-[(1S)-1-[1-[6-(trifluoromethyl)-4- pyrimidinyl]-1 H-1,2,4-triazol-5-yl]ethyl]-benzamide, 2-(3-ethylsulfonyl-2-pyridyl)-5-(2,2,3,3,3- pentafluoropropoxy)pyrazine, 2-[3-ethylsulfonyl-6-(trifluoromethyl)pyrazolo[1,5-a]pyridin-2-yl]-3- methyl-6-(trifluoromethyl)imidazo[4,5-b]pyridine, 9-(methoxymethyl)-5-(3-pyridyl)-2-oxa-5,6,9,14- tetrazatricyclo[8.4.0.0A{3,7}]tetradeca-1(10),3,6,11 ,13-pentaen-8-one, bisulfufen, 2-[5-[(E)-2- chloro-3,3,3-trifluoro-prop-1-enyl]-1-methyl-imidazol-2-yl]-5-cyclopropyl-3-ethylsulfonyl-pyridine, cybenzoxasulfyl, isoflualanam;

[0355] Bentioflumin, Vadescana, (3Z)-1-[2-fluoro-4-[1-[4-(trifluoromethoxy)phenyl]-1,2,4-triazol-3- yl]phenyl]-3-[3-[5-methyl-2-(2,2,2-trifluoroethoxymethyl)phenyl]-4-oxo-thiazolidin-2-ylidene]urea,

[0356] 1-[6-(2,2-difluoro-8-oxo-[1,3]dioxolo[4,5-g]chromen-7-yl)-5-ethylsulfonyl-3- pyridyl]cyclopropanecarbonitrile, 2-chloro-N-[(1S)-2-ethyl-1-methyl-butyl]furan-3-carboxamide, galquin, [5-cyclopropyl-2-[3-methyl-6-(trifluoromethyl)imidazo[4,5-b]pyridin-2-yl]-3-pyridyl]-ethyl- hydroxy-oxo-A6-sulfane, 4-[5-(3,5-dichloro-4-fluoro-phenyl)-5-(trifluoromethyl)-4H-isoxazol-3-yl]-

[0357] 2-methyl-N-[1-(2,2,2-trifluoroethylcarbamoyl)cyclopropyl]benzamide, 3-[3-ethylsulfonyl-7- (trifluoromethyl)imidazo[1,2-a]pyridin-2-yl]-7-(trifluoromethyl)chromen-4-one.

[0358] The commercially available compounds M listed above may be found in The Pesticide Man-ual, 18th Edition, C. MacBean, British Crop Protection Council (2018), or http: / / bcpcdata.com / pesticide-manual.html, http: / / www.alanwood.net / pesticides.

[0359] The active compounds described by IIIPAC nomenclature are known from CN103814937; WO2013 / 003977, W02007 / 101369, WO2018 / 177970, CN 10171577, CN 102126994, W02007 / 101540, W02007 / 043677, WO2011 / 085575, W02008 / 134969, WO2012 / 034403, W02006 / 089633, W02008 / 067911 , W02006 / 043635, W02009 / 124707, WO2013 / 050317, WO2010 / 060379, WO2010 / 127926, WO2010 / 006713, WO2012 / 000896, W02007 / 101369, WO2012 / 143317, WO2015 / 038503, EP2910126, WO2015 / 059039, W02015 / 190316, WO2012 / 126766, W02009 / 102736, WO2013 / 116053, WO2018 / 052136, WO2015150252, W02020055955, WO2021158455, W02013092350, WO201811111 , EP3608311, WO2019236274, W02013092350, WO 2018052136, W02009102736, WO2016174049, WO2012126766, CN 106554335, WO2017054524, CN 105153113, W02022072650; WO2018071327, W02022101502, WO2012158396, W02007079162, W02020013147, W02020097414, EP242081, WO2023058748, WO2017065228, EP3428166, W02021029308, W02022009058, W02017067500, W02020090585, WO2017146226, W02021043115, WO2023016278, W02021011722, WO2024126388, WO2024137594, EP4389739, WO2016096584, WO2024120137, WO2024188755, CN115925576, WO2024087613.

[0360] The following list of fungicides, in conjunction with which the compounds of the invention can be used, illustrates the possible combinations:

[0361] A) Respiration (C) complex III at Qosite (Qol, C3): azoxystrobin (A.1.1), bifemetstrobin (A.1.24), bifujunzhi (A.1.37), coumethoxystrobin (A.1.2), coumoxystrobin (A.1.3), dimoxystrobin (A.1.4), ene- stroburin (A.1.5), famoxadone (A.1.21), fenamidone (A.1.23), fenaminstrobin (A.1.6), flufen- oxystrobin (A.1.7), fluoxastrobin (A.1.8), kresoxim-methyl (A.1.9), mandestrobin (A.1.10), BASF SE 240867W001

[0362] B19464WO

[0363] 38 metominostrobin (A.1.11), metyltetraprole (A.1.25; member of MoA subgroup A), orysa- strobin (A.1.12), picoxystrobin (A.1.13), pyraclostrobin (A.1.14), pyrametostrobin (A.1.15), pyraoxystrobin (A.1.16), pyribencarb (A.1.19), pyriminostrobin (A.1.36), triclopyricarb (A.1.20), trifloxystrobin (A.1.17), 2-(2-(3-(2,6-dichlorophenyl)-1-methyl-allylideneaminooxy- methyl)-phenyl)-2-methoxyimino- / \ / -methyl-acetamide (A.1.18), methyl- / V-[2-[(1 ,4-dimethyl- 5-phenyl-pyrazol-3-yl)oxylmethyl]phenyl]- / V-methoxy-carbamate (A.1.22), (Z,2E)-5-[1-(2,4-di- chlorophenyl)pyrazol-3-yl]-oxy-2-methoxyimino-A / ,3-dimethyl-pent-3-enamide (A.1.34), (Z,2E)-5-[1-(4-chlorophenyl)pyrazol-3-yl]oxy-2-methoxyimino-A / ,3-dimethyl-pent-3-enamide (A.1 .35), 2-(ortho-((2,5-dimethylphenyl-oxymethylen)phenyl)-3-methoxy-acrylic acid methylester (A.1.38), methyl (Z)-3-methoxy-2-[2-methyl-5-(3-propylpyrazol-1-yl)phenoxy]- prop-2-enoate, methyl (Z)-2-[5-(3-isopropylpyrazol-1-yl)-2-methyl-phenoxy]-3-methoxy-prop- 2-enoate, methyl (Z)-3-methoxy-2-[2-methyl-5-[3-(trifluoromethyl)pyrazol-1-yl]phenoxy]prop-

[0364] 2-enoate, methyl (Z)-3-methoxy-2-[2-methyl-5-(4-propyltriazol-2-yl)phenoxy]prop-2-enoate, methyl (Z)-3-methoxy-2-[2-methyl-5-[4-(trifluoromethyl)triazol-2-yl]phenoxy]prop-2-enoate, methyl (Z)-2-[5-(4-isopropyltriazol-2-yl)-2-methyl-phenoxy]-3-methoxy-prop-2-enoate, methyl (Z)-2-(5-cyclobutyl-2-methyl-phenoxy)-3-methoxy-prop-2-enoate, methyl (Z)-2-(5-cyclopent- yl-2-methyl-phenoxy)-3-methoxy-prop-2-enoate, methyl (Z)-2-(5-cyclopropyl-2-methyl-phen- oxy)-3-methoxy-prop-2-enoate, methyl (Z)-2-(5-cyclohexyl-2-methyl-phenoxy)-3-methoxy- prop-2-enoate, methyl (E)-3-methoxy-2-[(2-methyl-5-phenyl-phenyl)methyl]prop-2-enoate, methyl (E)-3-methoxy-2-[[5-[(E)- / V-methoxy-C-methyl-carbonimidoyl]-2,4-dimethyl-phenyl]- methyl]prop-2-enoate; methyl (E)-2-[[5-(2-cyclopropylethynyl)-2,4-dimethyl-phenyl]methyl]-

[0365] 3-methoxy-prop-2-enoate; methyl (E)-3-methoxy-2-(2-phenyl-1 ,3-benzoxazol-4-yl)prop- 2-enoate; methyl (E)-3-methoxy-2-(2-phenyl-1 ,3-benzothiazol-4-yl)prop-2-enoate; methyl (E)-3-methoxy-2-(2-phenyl-1 ,3-benzoxazol-7-yl)prop-2-enoate; methyl (Z)-2-[6-(2-cycloprop- ylethynyl)benzimidazol-1-yl]-3-methoxy-prop-2-enoate; methyl (Z)-3-methoxy-2-(6-phenyl- benzimidazol-1-yl)prop-2-enoate; methyl (Z)-2-(3-chloro-6-phenyl-indol-1-yl)-3-methoxy- prop-2-enoate; methyl (Z)-2-(2,3-dichloro-6-phenyl-indol-1-yl)-3-methoxy-prop-2-enoate; methyl (Z)-3-methoxy-2-[6-[(E)-methoxyiminomethyl]indol-1-yl]prop-2-enoate; methyl (Z)-3-methoxy-2-[6-[(E)- / V-methoxy-C-methyl-carbonimidoyl]indol-1-yl]prop-2-enoate, methyl / V-[[5-[1-(2,6-difluoro-4-isopropyl-phenyl)pyrazol-3-yl]-2-methyl-phenyl]methyl]carbamate, methyl / V-[[5-[1-(4-cyclopropyl-2,6-difluoro-phenyl)pyrazol-3-yl]-2-methyl-phenyl]methyl]- carbamate, methyl / V-[[5-[1-(4-chloro-2,6-difluoro-phenyl)pyrazol-3-yl]-2-methyl-phenyl]- methyl]carbamate, methyl / \ / -[[5-[1 -[2,6-difluoro-4-(trifluoromethyl)phenyl]pyrazol-3-yl]- 2-methyl-phenyl]methyl]carbamate;

[0366] - complex III at Qi site (Qil, C4): cyazofamid (A.2.1), amisulbrom (A.2.2), [(6S,7R,8R)-8-benzyl-3-[(3-hydroxy-4-methoxy-pyridine-2-carbonyl)amino]-6-methyl-4,9-di- oxo-1 , 5-dioxonan-7-yl]-2-methylpropanoate (A.2.3), fenpicoxamid (A.2.4), florylpicoxamid (A.2.5), metarylpicoxamid (A.2.6);

[0367] - complex II (SDHI, C2): benodanil (A.3.1), benzovindiflupyr (A.3.2), bixafen (A.3.3), boscalid (A.3.4), carboxin (A.3.5), cyclobutrifluram (A.3.24), fenfuram (A.3.6), fluopyram (A.3.7), flutolanil (A.3.8), fluxapyroxad (A.3.9), furametpyr (A.3.10), inpyrfluxam (A.3.22), isofetamid (A.3.11), isoflucypram (A.3.31), isopyrazam (A.3.12), mepronil (A.3.13), oxycarboxin

[0368] (A.3.14), penflufen (A.3.15), penthiopyrad (A.3.16), pydiflumetofen (A.3.17), pyrapropoyne (A.3.23), pyraziflumid (A.3.18), sedaxane (A.3.19), tecloftalam (A.3.20), thifluzamide BASF SE 240867W001

[0369] B19464WO

[0370] 39

[0371] (A.3.21), fluindapyr (A.3.28), / V-[2-[2-chloro-4-(trifluoromethyl)phenoxy]phenyl]- 3-(difluoromethyl)-5-fluoro-1-methyl-pyrazole-4-carboxamide (A.3.29), methyl (E)-2-[2-[(5-cy- ano-2-methyl-phenoxy)methyl]phenyl]-3-methoxy-prop-2-enoate (A.3.30), 2-(difluoromethyl)- / V-(1 ,1 ,3-trimethyl-indan-4-yl)pyridine-3-carboxamide (A.3.32), 2-(difluoromethyl)- A / -[(3R)-1 ,1 ,3-trimethylindan-4-yl]pyridine-3-carboxamide (A.3.33), 2-(difluoromethyl)- / V-(3-ethyl-1 ,1-dimethyl-indan-4-yl)pyridine-3-carboxamide (A.3.34), 2-(difluoromethyl)- / V-[(3R)-3-ethyl-1 ,1-dimethyl-indan-4-yl]pyridine-3-carboxamide (A.3.35), 2-(difluoromethyl)- / V-(1 ,1-dimethyl-3-propyl-indan-4-yl)pyridine-3-carboxamide (A.3.36), 2-(difluoromethyl)- / V-[(3R)-1 ,1-dimethyl-3-propyl-indan-4-yl]pyridine-3-carboxamide (A.3.37), 2-(difluoromethyl)- / V-(3-isobutyl-1 ,1-dimethyl-indan-4-yl)pyridine-3-carboxamide (A.3.38), 2-(difluoromethyl)- / V-[(3R)-3-isobutyl-1 ,1-dimethyl-indan-4-yl]pyridine-3-carboxamide (A.3.39);

[0372] - complex I NADH oxido-reductase (C1): diflumetorim (A.4.1);

[0373] - uncouplers (C5): binapacryl (A.4.2), dinobuton (A.4.3), dinocap (A.4.4), fluazinam (A.4.5), meptyldinocap (A.4.6), ferimzone (A.4.7);

[0374] - inhibitors of ox. phosphorylation (C6): fentin salts, e.g. fentin-acetate (A.4.8), fentin chloride (A.4.9) or fentin hydroxide (A.4.10);

[0375] - ATP transport: silthiofam (A.4.11);

[0376] - quinone inside and outside inhibitor stigmatellin binding type (QioSI; C8): ametoctradin (A.5.1);

[0377] B) Sterol biosynthesis (G)

[0378] - C14 demethylase (DMI, G1): triazoles: azaconazole (B.1.1), bitertanol (B.1.2), bromucon- azole (B.1.3), cyproconazole (B.1.4), difenoconazole (B.1.5), diniconazole (B.1.6), dinicon- azole-M (B.1.7), epoxiconazole (B.1.8), fenbuconazole (B.1.9), fluoxytioconazole (B.1.33), fluquinconazole (B.1.10), flusilazole (B.1.11), flutriafol (B.1.12), hexaconazole (B.1.13), imi- benconazole (B.1.14), ipconazole (B.1.15), ipfentrifluconazole (B.1.37), mefentrifluconazole (B.1.38), metconazole (B.1.17), myclobutanil (B.1.18), oxpoconazole (B.1.19), paclobutra- zole (B.1.20), penconazole (B.1.21), propiconazole (B.1.22), prothioconazole (B.1.23), simeconazole (B.1.24), tebuconazole (B.1.25), tetraconazole (B.1.26), triadimefon (B.1.27), triadimenol (B.1.28), triticonazole (B.1.29), uniconazole (B.1.30), 2-(2,4-difluorophenyl)- 1 ,1-difluoro-3-(tetrazol-1-yl)-1-[5-[4-(2,2,2-trifluoroethoxy)phenyl]-2-pyridyl]propan-2-ol

[0379] (B.1.31), 2-(2,4-difluorophenyl)-1 ,1-difluoro-3-(tetrazol-1-yl)-1-[5-[4-(trifluoromethoxy)phenyl]-

[0380] 2-pyridyl]propan-2-ol (B.1.32), 2-(chloromethyl)-2-methyl-5-(p-tolylmethyl)-1-(1 ,2,4-triazol-

[0381] 1-ylmethyl)cyclopentanol (B.1.43), 4-[[6-[2-(2,4-difluorophenyl)-1 ,1-difluoro-2-hydroxy-

[0382] 3-(1 ,2,4-triazol-1-yl)propyl]-3-pyridyl]oxy]benzonitrile (B.1 .53), 2-[6-(4-bromophenoxy)-

[0383] 2-(trifluoromethyl)-3-pyridyl]-1-(1 ,2,4-triazol-1-yl)propan-2-ol (B.1.54), 2-[6-(4-chlorophen- oxy)-2-(trifluoromethyl)-3-pyridyl]-1-(1 ,2,4-triazol-1-yl)propan-2-ol (B.1.55), (2R)-2-[4-(4-chlo- rophenoxy)-2-(trifluoromethyl)phenyl]-1-(1 ,2,4-triazol-1-yl)propan-2-ol, (2S)-2-[4-(4-chlo- rophenoxy)-2-(trifluoromethyl)phenyl]-1-(1 ,2,4-triazol-1-yl)propan-2-ol, methyl 2-[2-chloro-

[0384] 4-(4-chlorophenoxy)phenyl]-2-hydroxy-3-(1 ,2,4-triazol-1-yl)propanoate (B.1 .56), 2-[2-chloro- 4-(4-chlorophenoxy)phenyl]-2-hydroxy-3-(1 ,2,4-triazol-1-yl)propanoic acid (B.1.57); imidazoles: imazalil (B.1.44), pefurazoate (B.1.45), prochloraz (B.1.46), triflumizole (B.1.47); pyrimidines, pyridines, piperazines: fenarimol (B.1.49), pyrifenox (B.1.50), triforine (B.1.51), [3-(4-chloro-2-fluoro-phenyl)-5-(2,4-difluorophenyl)isoxazol-4-yl]-(3-pyridyl)methanol

[0385] (B.1.52); BASF SE 240867W001

[0386] B19464WO

[0387] 40

[0388] - delta14-reductase (G2): aldimorph (B.2.1), dodemorph (B.2.2), dodemorph-acetate (B.2.3), fenpropidin (B.2.6), fenpropimorph (B.2.4), piperalin (B.2.7), spiroxamine (B.2.8), tridemorph (B.2.5);

[0389] - 3-keto reductase (G3): fenhexamid (B.3.1), fenpyrazamine (B.3.2);

[0390] - other: chlorphenomizole (B.4.1);

[0391] C) Nucleic acids metabolism (A)

[0392] - RNA polymerase I (A1): benalaxyl (C.1.1), benalaxyl-M (C.1.2), kiralaxyl (C.1.3), metalaxyl (C.1.4), metalaxyl-M (C.1.5), ofurace (C.1.6), oxadixyl (C.1.7);

[0393] - adenosine deaminase (A2): bupirimate (C.2.4), 5-fluoro-2-(p-tolylmethoxy)pyrimidin-4-amine (C.2.6), 5-fluoro-2-(4-fluorophenylmethoxy)pyrimidin-4-amine (C.2.7), 5-fluoro-2-(4-chloro- phenylmethoxy)pyrimidin-4-amine (C.2.8);

[0394] - DNA / RNA synthesis (A3): 5-fluorocytosine (C.2.5), hymexazole (C.2.1), octhilinone (C.2.2),

[0395] - gyrase (A4): oxolinic acid (C.2.3);

[0396] - dihydroo rotate dehydrogenase (DHODH; A5): ipflufenoquin (C.5.1), quinofumelin (C.5.2), feneptamidoquin (C.5.3);

[0397] D) Cytoskeleton and motor protein (B)

[0398] - tubulin polymerization (MBC; B1): benomyl (D.1.1), carbendazim (D.1.2), fuberidazole (D.1.3), pyridachlometyl (D.1.6), thiabendazole (D.1.4), thiophanate-methyl (D.1.5), / V-ethyl-

[0399] 2-[(3-ethynyl-8-methyl-6-quinolyl)oxy]butanamide (D.1 .8), / \ / -ethyl-2-[(3-ethynyl-8-methyl- 6-quinolyl)oxy]-2-methylsulfanyl-acetamide (D.1.9), 2-[(3-ethynyl-8-methyl-6-quinolyl)oxy]- / \ / -(2-fluoroethyl)butanamide (D.1.10), 2-[(3-ethynyl-8-methyl-6-quinolyl)oxy]- / \ / -(2-fluoroeth- yl)-2-methoxy-acetamide (D.1 .11), 2-[(3-ethynyl-8-methyl-6-quinolyl)oxy]- / \ / -propyl- butanamide (D.1.12), 2-[(3-ethynyl-8-methyl-6-quinolyl)oxy]-2-methoxy- / \ / -propyl-acetamide (D.1.13), 2-[(3-ethynyl-8-methyl-6-quinolyl)oxy]-2-methylsulfanyl- / \ / -propyl-acetamide

[0400] (D.1.14), 2-[(3-ethynyl-8-methyl-6-quinolyl)oxy]- / \ / -(2-fluoroethyl)-2-methylsulfanyl-acetamide (D.1.15), 4-(2-bromo-4-fluoro-phenyl)- / V-(2-chloro-6-fluoro-phenyl)-2,5-dimethyl-pyrazol-

[0401] 3-amine (D.1.16), 4-(2-bromo-4-fluorophenyl)- / V-(2-fluoro-6-nitrophenyl)-1 ,3-dimethyl-

[0402] 1 / 7-pyrazol-5-amine, 4-(2-chloro-4,6-difluorophenyl)- / V-(2-fluoro-6-nitrophenyl)-1 ,3-dimethyl- 1 / 7-pyrazol-5-amine, 4-(2-chloro-4-fluorophenyl)- / V-(2-fluoro-6-nitrophenyl)-3-ethyl-1-methyl- 1 / 7-pyrazol-5-amine, 4-(2-chloro-4-fluorophenyl)- / V-(2-fluoro-4-methyl-6-nitrophenyl)-1 ,3-di- methyl-1 / 7-pyrazol-5-amine, 4-(2-chloro-4-fluorophenyl)- / V-(2-fluoro-6-nitrophenyl)-1 ,3-di- methyl-1 / 7-pyrazol-5-amine, 4-(2,4-difluorophenyl)- / V-(2-fluoro-6-nitrophenyl)-1 ,3-dimethyl- 1 / 7-pyrazol-5-amine;

[0403] - tubulin polymerization (B2): diethofencarb (D.2.1),

[0404] - tubulin polymersation (B3): ethaboxam (D.2.2), zoxamide (D.2.5);

[0405] - cell division (B4): pencycuron (D.2.3);

[0406] - spectrin-like proteins (B5): fluopicolide (D.2.4), fluopimomide (D.2.9);

[0407] - actin / myosin / fimbrin function (B6): metrafenone (D.2.6), phenamacril (D.2.8), pyriofenone (0-2.7);

[0408] E) Amino acids and protein synthesis (D)

[0409] - methionine synthesis (D1): cyprodinil (E.1.1), mepanipyrim (E.1.2), pyrimethanil (E.1.3);

[0410] - ribosome, termination step (D2): blasticidin-S (E.2.1);

[0411] - ribosome initiation step (D3): kasugamycin (E.2.2), kasugamycin hydrochloride-hydrate (E.2.3); BASF SE 240867W001

[0412] B19464WO

[0413] 41

[0414] - ribosome initiation step (D4): streptomycin (E.2.5);

[0415] - ribosome elongation step (D5): mildiomycin (E.2.4), oxytetracyclin (E.2.6);

[0416] F) Signal transduction

[0417] - mechanism unknown (E1): proquinazid (F.2.2), quinoxyfen (F.2.1);

[0418] - MAP / histidine kinase os-2 (E2): fludioxonil (F.1.5);

[0419] - MAP / histidine kinase os-1 (E3): iprodione (F.1.2), procymidone (F.1.3), vinclozolin (F.1.4);

[0420] G) Lipid synthesis or transport / membrane (F)

[0421] - methyl transferase (F2): edifenphos (G.1.1), iprobenfos (G.1.2), isoprothiolane (G.1.4); pyrazophos (G.1.3);

[0422] - cell peroxidation (F3): biphenyl (G.2.5), chloroneb (G.2.6), dicloran (G.2.1), etridiazole (G.2.7), quintozene (G.2.2), tecnazene (G.2.3), tolclofos-methyl (G.2.4);

[0423] - cell membrane permeability (F4): propamocarb (G.4.1);

[0424] - ergosterol binding (F8): natamycin;

[0425] - oxysterol binding protein (F9): fluoxapiprolin (G.5.3), oxathiapiprolin (G.5.1), 4-[1-[2-[3-(di- fluoromethyl)-5-methyl-pyrazol-1-yl]acetyl]-4-piperidyl]- / \ / -tetralin-1-yl-pyridine-2-carboxamide (G.5.4), 4-[1 -[2-[3,5-bis(difluoromethyl)pyrazol-1 -yl]acetyl]-4-piperidyl]- / \ / -tetralin-1 -yl-pyri- dine-2-carboxamide (G.5.5), 4-[1-[2-[3-(difluoromethyl)-5-(trifluoromethyl)pyrazol-1-yl]acetyl]- 4-piperidyl]- / V-tetralin-1-yl-pyridine-2-carboxamide (G.5.6), 4-[1-[2-[5-cyclopropyl-3-(difluoro- methyl)pyrazol-1-yl]acetyl]-4-piperidyl]- / \ / -tetralin-1-yl-pyridine-2-carboxamide (G.5.7),

[0426] 4-[1 -[2-[5-methyl-3-(trifluoromethyl)pyrazol-1 -yl]acetyl]-4-piperidyl]- / \ / -tetralin-1 -yl-pyridine- 2-carboxamide (G.5.8), 4-[1-[2-[5-(difluoromethyl)-3-(trifluoromethyl)pyrazol-1-yl]acetyl]-4-pi- peridyl]- / V-tetralin-1-yl-pyridine-2-carboxamide (G.5.9), 4-[1-[2-[3,5-bis(trifluoromethyl)pyr- azol-1-yl]acetyl]-4-piperidyl]- / \ / -tetralin-1-yl-pyridine-2-carboxamide (G.5.10), (4-[1-[2-[5-cy- clopropyl-3-(trifluoromethyl)pyrazol-1-yl]acetyl]-4-piperidyl]- / \ / -tetralin-1-yl-pyridine-2-carbox- amide (G.5.11), (1-(4-(4-(5-(2,6-dichlorophenyl)-4,5-dihydroisoxazol-3-yl)thiazol-2-yl)piper- idin-1-yl)-2-((3-trifluoromethyl)pyrazin-2-yl)oxy)ethan-1-one, 1-(4-(4-(5-(2-chloro-6-fluoro- phenyl)-4,5-dihydroisoxazol-3-yl)thiazol-2-yl)piperidin-1-yl)-2-((3-trifluoromethyl)pyridin-2-yl)- oxy)ethan-1-one, tert-butyl 4-(4-(5-(2-bromo-6-fluorophenyl)-4,5-dihydroisoxazol-3-yl)thiazol- 2-yl)piperidin-1 -carboxylate, ((2-(3-(2-(1-(2-(3,5-bis(trifluoromethyl)-1 / 7-pyrazol-1-yl)acetyl)- piperidin-4-yl)thiazol-4-yl)-4,5-dihydroisoxazo-5-yl)-3-fluorophenyl)imino)dimethyl-A6-sulfa- none, ((2-(3-(2-(1-(2-(3,5-bis(difluoromethyl)-1 / 7-pyrazol-1-yl)acetyl)piperidin-4-yl)thiazol- 4-yl)-4,5-dihydroisoxazo-5-yl)-3-fluorophenyl)imino)dimethyl-A6-sulfanone, ((2-(3-(2-(1-(2-(3,5-bis(difluoromethyl)-1 / 7-pyrazol-1-yl)acetyl)piperidin-4-yl)thiazol-4-yl)-

[0427] 4.5-dihydroisoxazo-5-yl)-3-chorophenyl)imino)(isopropyl)(methyl)-A6-sulfanone, ((2-(3-(2-(1-(2-(3,5-bis(trifluoromethyl)-1 / 7-pyrazol-1-yl)acetyl)piperidin-4-yl)thiazol-4-yl)-

[0428] 4.5-dihydroisoxazo-5-yl)-3-fluorophenyl)imino)(isopropyl)(methyl)-A6-sulfanone, ((2-(3-(2-(1-(2-(3,5-bis(difluoromethyl)-1 / 7-pyrazol-1-yl)acetyl)piperidin-4-yl)thiazol-4-yl)-

[0429] 4.5-dihydroisoxazo-5-yl)-3-(trifluoromethyl)phenyl)imino)dimethyl-A6-sulfanone, ((3-fluoro- 2-(3-(2-(1-(2-(5-methyl-3-(trifluoromethyl)-1 / 7-pyrazol-1-yl)acetyl)piperidin-4-yl)thiazol-4-yl)-

[0430] 4.5-dihydroisoxazo-5-yl)-phenyl)imino)dimethyl-A6-sulfanone;

[0431] H) Multi Site Activity (M)

[0432] - inorganics (M01): Bordeaux mixture (H.1.1), copper (H.1.2), copper acetate (H.1.3), copper hydroxide (H.1.4), copper oxychloride (H.1.5), basic copper sulfate (H.1.6), sulfur (H.1.7);

[0433] - dithiocarbamates and relatives: ferbam (H.2.1), mancozeb (H.2.2), maneb (H.2.3), metam BASF SE 240867W001

[0434] B19464WO

[0435] 42

[0436] (H.2.4), metiram (H.2.5), propineb (H.2.6), thiram (H.2.7), zineb (H.2.8), ziram (H.2.9), zinc thiazole (H.2.10);

[0437] - organochlorine compounds (M04, M05, M06, M08): anilazine (H.3.1), captafol (H.3.3), captan (H.3.4), chlorothalonil (H.3.2), dichlofluanid (H.3.6), dichlorophen (H.3.7), folpet (H.3.5), hexachlorobenzene (H.3.8), pentachlorphenole (H.3.9) and its salts, phthalide (H.3.10), tolylfluanid (H.3.11);

[0438] - guanidines, quinones, quinoxalines, maleimides, thiocarbamates (M07, M09, M10, M11, M12): chinomethionat (H.4.13), dithianon (H.4.9), fluoroimide (H.4.11), guanidine (H.4.1), guazatine (H.4.4), guazatine-acetate (H.4.5), iminoctadine (H.4.6), iminoctadine-triacetate (H.4.7), iminoctadine-tris(albesilate) (H.4.8), methasulfocarb (H.4.12), 2,6-dimethyl-

[0439] 1 / 7,5 / 7-[1 , 4]d ithi i no[2 , 3-c: 5, 6-c']d i pyrrole- 1 ,3,5,7(2H,6H)-tetraone (H.4.10),

[0440] I) Cell wall biosynthesis (H) and melanin synthesis in cell wall (I)

[0441] - chitin synthase (H4): polyoxin B (1.1.2);

[0442] - cellulose synthase (H5): benthiavalicarb (1.3.5), dimethomorph (1.3.1), flumorph (1.3.2), iprovalicarb (1.3.6), mandipropamid (1.3.3), pyrimorph (1.3.4), valifenalate (1.3.7);

[0443] - reductase in melanin synthesis (MBI-R; 11) pyroquilon (1.2.1), tricyclazole (1.2.2);

[0444] - dehydratase in melanin synthesis (MBI-D, I2); carpropamid (1.2.3), dicyclomet (1.2.4), fenoxanil (1.2.5);

[0445] - polyketide synthase in melanin synthesis (MBI-P, I3): tolprocarb (1.2.6);

[0446] J) Plant defence induction (P1 to P8)

[0447] - salicylate-related (P01-P03, P08): acibenzolar-S-methyl (J.1.1), probenazole (J.1.2), isotianil (J.1.3), tiadinil (J.1.4), dichlobentiazox (J.1.13); phosphonates (P07): fosetyl (J.1.6), fosetyl- aluminum (J.1.7), phosphorous acid and its salts (J.1.8), calcium phosphonate (J.1.11), potassium phosphonate (J.1.12); others: potassium or sodium bicarbonate (J.1.9), 4-cyclo- propyl- / V-(2,4-dimethoxyphenyl)thiadiazole-5-carboxamide (J.1.10);

[0448] K) Unknown mode of action (U)

[0449] - aminopyrifen (K.1.54), benziothiazolinone (K.1.48), bromothalonil (K.1.49), bronopol (K.1.1), cyflufenamid (K.1.3), cymoxanil (K.1.4), dazomet (K.1.5), debacarb (K.1.6), diclomezine (K.1.8), difenzoquat (K.1.9), difenzoquat-methylsulfate (K.1.10), diphenylamin (K.1.11), dodine, dodine free base (K.1.18), fenitropan (K.1.12), flufenoxadiazam (K.1.58) [MoA proposed: class II histone deacetylase inhibitor], flumetover (K.1.14), flumetylsulforim (K.1.60), flusulfamide (K.1.15), flutianil (K.1.16), harpin (K.1.17), nitrapyrin (K.1.19), nitrothal- isopropyl (K.1.20), oxine-copper (K.1.22), picarbutrazox (K.1.41), pyrisoxazole (K.1.37), seboctylamine (K.1.61), tebufloquin (K.1.24), tecloftalam (K.1.25), triazoxide (K.1.26), validamycin (K.1.2); / V-(4-(4-chloro-3-trifluoromethyl-phenoxy)-2,5-dimethyl-phenyl)- / \ / -ethyl- / V-methyl formamidine (K.1.27), / V-(4-(4-fluoro-3-trifluoromethyl-phenoxy)-2,5-dimethyl- phenyl)- / V-ethyl- / \ / -methyl formamidine (K.1.28), / \ / -[4-[[3-[(4-chlorophenyl)methyl]-1 ,2,4-thia- diazol-5-yl]oxy]-2,5-dimethyl-phenyl]- / V-ethyl- / V-methyl-formamidine (K.1.29), / V -(5-bromo- 6-indan-2-yloxy-2-methyl-3-pyridyl)- / V-ethyl- / V-methyl-formamidine (K.1.30), / V -[5-bromo- 6-[1-(3,5-difluorophenyl)ethoxy]-2-methyl-3-pyridyl]- / \ / -ethyl- / \ / -methyl-formamidine (K.1.31), / V-[5-bromo-6-(4-isopropylcyclohexoxy)-2-methyl-3-pyridyl]- / \ / -ethyl- / \ / -methyl-formamidine (K.1.32), / V-[5-bromo-2-methyl-6-(1-phenylethoxy)-3-pyridyl]- / \ / -ethyl- / \ / -methyl-formamidine (K.1.33), / V -(2-methyl-5-trifluoromethyl-4-(3-trimethylsilanyl-propoxy)-phenyl)- / \ / -ethyl- / V-methyl formamidine (K.1.34), / V-(5-difluoromethyl-2-methyl-4-(3-trimethylsilanyl-propoxy)- BASF SE 240867W001

[0450] B19464WO

[0451] 43 phenyl)- / V-ethyl- / V-methyl formamidine (K.1.35), 2-(4-chloro-phenyl)- / V-[4-(3,4-dimethoxy- phenyl)-isoxazol-5-yl]-2-prop-2-ynyloxy-acetamide (K.1 .36), 3-[5-(4-methylphenyl)-2,3-di- methyl-isoxazolidin-3-yl]-pyridine (K.1.38), 5-chloro-1-(4,6-dimethoxy-pyrimidin-2-yl)-2-meth- yl-1 / - / -benzoimidazole (K.1.39), ethyl (Z)-3-amino-2-cyano-3-phenyl-prop-2-enoate (K.1.40), pentyl / V-[6-[[(Z)-[(1-methyltetrazol-5-yl)-phenyl-methylene]amino]oxymethyl]-2-pyridyl]carba- mate (K.1.42), but-3-ynyl / V-[6-[[(Z)-[(1-methyltetrazol-5-yl)-phenyl-methylene]amino]oxy- methyl]-2-pyridyl]carbamate (K.1.43), 2-(6-benzyl-2-pyridyl)quinazoline (K.1.50), 2-[6-(3-flu- oro-4-methoxy-phenyl)-5-methyl-2-pyridyl]quinazoline (K.1.51), / \ / -(2,5-dimethyl-4-phenoxy- phenyl)- / V-ethyl- / V-methyl-formamidine (K.1.53), / V'-[5-bromo-2-methyl-6-(1-methyl-2-prop- oxy-ethoxy)-3-pyridyl]- / V-ethyl- / V-methyl-formamidine (K.1.56), / V -[4-(4,5-dichlorothiazol- 2-yl)oxy-2,5-dimethyl-phenyl]- / V-ethyl- / V-methyl-formamidine (K.1.57), / V-methyl-4-[5-(tri- fluoromethyl)-1 ,2,4-oxadiazol-3-yl]benzenecarbothioamide (K.1.59), / V-methoxy- / V-[[4-[5-(tri- fluoromethyl)-1 ,2,4-oxadiazol-3-yl]phenyl]methyl]cyclopropanecarboxamide (K.1 .61), / V-((4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-3-yl]phenyl)methyl)propanamide (K.1.62), 3,3,3-tri- fluoro- / V-[[3-fluoro-4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-3-yl]phenyl]methyl]propanamide (K.1 .63), 3,3,3-trifluoro- / V-[[2-fluoro-4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-3-yl]phenyl]methyl]- propanamide (K.1.64), / V-[2,3-difluoro-4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-3-yl]benzyl]- butanamide (K.1.65), / V-[[2,3-difluoro-4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-3-yl]phenyl]- methyl]-3,3,3-trifluoro-propanamide (K.1.66), 1-methoxy-1-methyl-3-[[4-[5-(trifluoromethyl)- 1 ,2,4-oxadiazol-3-yl]phenyl]methyl]urea (K.1.67), 1 ,1-diethyl-3-[[4-[5-[trifluoromethyl]-

[0452] 1 .2.4-oxadiazol-3-yl]phenyl]methyl]urea (K.1 .68), / V,2-dimethoxy- / V-[[4-[5-(trifluoromethyl)-

[0453] 1 .2.4-oxadiazol-3-yl]phenyl]methyl]propanamide (K.1.69), A / -ethy l-2-methy l- / \ / -[[4-[5-(trifl uoro- methyl)-1 ,2,4-oxadiazol-3-yl]phenyl]methyl]propanamide (K.1.70), 1-methoxy-3-methyl-

[0454] 1-[[4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-3-yl]phenyl]methyl]urea (K.1.71), 1-[[4-[5-(trifluoro- methyl)-1 ,2,4-oxadiazol-3-yl]phenyl]methyl]pyrrolidin-2-one (K.1.72), 1-[[4-[5-(trifluoro- methyl)-1 ,2,4-oxadiazol-3-yl]phenyl]methyl]piperidin-2-one (K.1.73), 4-[[4-[5-(trifluoromethyl)-

[0455] 1 .2.4-oxadiazol-3-yl]phenyl]methyl]morpholin-3-one (K.1.74), 4,4-dimethyl-2-[[4-[5-(trifluoro- methyl)-1 ,2,4-oxadiazol-3-yl]phenyl]methyl]isoxazolidin-3-one (K.1.75), 2-[[4-[5-(trifluoro- methyl)-1 ,2,4-oxadiazol-3-yl]phenyl]methyl]isoxazolidin-3-one (K.1.76), 5,5-dimethyl-

[0456] 2-[[4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-3-yl]phenyl]methyl]isoxazolidin-3-one (K.1 .77), 3,3-dimethyl-1-[[4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-3-yl]phenyl]methyl]piperidin-2-one (K.1.78), 2-[[4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-3-yl]phenyl]methyl]oxazinan-3-one

[0457] (K.1.79), 1-[[3-fluoro-4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-3-yl]phenyl]methyl]azepan-2-one (K.1.80), 4,4-dimethyl-1-[[4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-3-yl]phenyl]methyl]pyrrolidin-

[0458] 2-one (K.1.81), 5-methyl-1-[[4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-3-yl]phenyl]methyl]- pyrrolidin-2-one (K.1.82), ethyl 1-[[4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-3-yl]phenyl]methyl]- pyrazole-4-carboxylate (K.1.83), / V-methyl-1-[[4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-3-yl]- phenyl]methyl]pyrazole-4-carboxamide (K.1.84), / V, / V-dimethyl-1-[4-[5-(trifluoromethyl)-

[0459] 1.2.4-oxadiazol-3-yl]benzyl]-1 / 7-1 ,2,4-triazol-3-amine (K.1.85), / V-methoxy-ZV-methyl- 1-[[4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-3-yl]phenyl]methyl]pyrazole-4-carboxamide (K.1.86), propyl-1-[[4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-3-yl]phenyl]methyl]pyrazole- 4-carboxamide (K.1.87), / V-methoxy-1-[[4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-3-yl]phenyl]- methyl]pyrazole-4-carboxamide (K.1.88), / V-al ly I- / -[[4-[5-(trifl uoromethy I)- 1 ,2,4-oxadiazol-

[0460] 3-yl]phenyl]methyl]propanamide (K.1.89), 3-ethyl-1-methoxy-1-[[4-[5-(trifluoromethyl)- BASF SE 240867W001

[0461] B19464WO

[0462] 44

[0463] 1 ,2,4-oxadiazol-3-yl]phenyl]methyl]urea (K.1.90), 1 ,3-dimethoxy-1-[[4-[5-(trifluoromethyl)-

[0464] 1 .2.4-oxadiazol-3-yl]phenyl]methyl]urea (K.1 .91), A / -allyl-A / -[[4-[5-(trifl uoromethyl)- 1 ,2,4-oxa- diazol-3-yl]phenyl]methyl]acetamide (K.1.92), / V- [4- [5- (tri fl uoromethyl)- 1 ,2,4-oxadiazol-3-yl]- benzyl]cyclopropanecarboxamide (K.1.93), 1-methyl-3-[[4-[5-(trifluoromethyl)-1 ,2,4-oxadi- azol-3-yl]phenyl]methyl]urea (K.1 .94), / V'-[2-chloro-4-(2-fluorophenoxy)-5-methyl-phenyl]- / V-ethyl- / V-methyl-formamidine (K.1.95), / V'-[2-chloro-4-[(4-methoxy-phenyl)methyl]-5-methyl- phenyl]- / V-ethyl- / \ / -methyl-formamidine (K.1.96), / V'-[2-chloro-4-[(4-cyano-phenyl)methyl]- 5-methyl-phenyl]- / \ / -ethyl- / \ / -methyl-formamidine (K.1.97), / V '-[2,5-dimethyl-4-(o-tolylmethyl)- phenyl]- / V-ethyl-N-methyl-formamidine (K.1 .98), 6-chloro-3-(3-cyclopropyl-2-fluoro-phenoxy)- / V-[2-(2,4-dimethylphenyl)-2,2-difluoro-ethyl]-5-methyl-pyridazine-4-carboxamide (K.1.99),

[0465] 3-(3-bromo-2-fluoro-phenoxy)-6-chloro- / V-[2-(2-chloro-4-methyl-phenyl)-2,2-difluoro-ethyl]- 5-methyl-pyridazine-4-carboxamide (K.1.100), 6-chloro- / V-[2-(2-chloro-4-methyl-phenyl)- 2,2-difluoro-ethyl]-3-(3-cyclopropyl-2-fluoro-phenoxy)-5-methyl-pyridazine-4-carboxamide (K.1.101), 6-chloro-3-(3-cyclopropyl-2-fluoro-phenoxy)- / \ / -[2-(3,4-dimethylphenyl)-2,2-diflu- oro-ethyl]-5-methyl-pyridazine-4-carboxamide (K.1.102), 6-chloro-3-(3-chloro-2-fluoro-phen- oxy)- / V-[2-(2,4-dimethylphenyl)-2,2-difluoro-ethyl]-5-methyl-pyridazine-4-carboxamide

[0466] (K.1.103), / V-[2-(2-bromo-4-methyl-phenyl)-2,2-difluoro-ethyl]-6-chloro-3-(3-cyclopropyl-2-flu- oro-phenoxy)-5-methyl-pyridazine-4-carboxamide (K.1.104), 2-[cyano-(2,6-difluoro-4-pyri- dyl)amino]-5-methyl- / V-spiro[3.4]octan-3-yl-thiazole-4-carboxamide, 2-[acetyl-(2,6-difluoro-

[0467] 4-pyridyl)arnino]- / V-(2,2-dimethylcyclobutyl)-5-methyl-thiazole-4-carboxamide, 2-[(2,6-di- fluoro-4-pyridyl)-(2-methoxyacetyl)amino]- / V-(2,2-dimethylcyclobutyl)-5-methyl-thiazole-

[0468] 4-carboxamide, 2-[cyano-(2,6-difluoro-4-pyridyl)amino]- / \ / -(2,2-dimethylcyclobutyl)-5-methyl- thiazole-4-carboxamide, / \ / -[1-[[3-[2-(5-fluoro-2-methoxy-phenyl)-2-hydroxy-ethyl]-

[0469] 5-[(Z)- / V-isopropoxy-C-methyl-carbonimidoyl]-2,6-dioxo-pyrimidin-1-yl]methyl]-2-methyl- propyl]-2-methyl-propanamide, / V-[1-[[3-[2-(5-fluoro-2-methoxy-phenyl)-2-hydroxy-ethyl]- 5-[(Z)- / V-isopropoxy-C-methyl-carbonimidoyl]-2,6-dioxo-pyrimidin-1-yl]methyl]-2-methyl- propyl]-2,2-dimethyl-propanamide, / \ / -[2-[3-[2-(5-fluoro-2-methoxy-phenyl)-2-hydroxy-ethyl]- 5-[(Z)- / V-isopropoxy-C-methyl-carbonimidoyl]-2,6-dioxo-pyrimidin-1-yl]-1-methyl-ethyl]- 2-methyl-propanamide, / \ / -[2-[3-[2-hydroxy-2-(2-methoxyphenyl)ethyl]-5-[(Z)- / \ / -isopropoxy- C-methyl-carbonimidoyl]-2,6-dioxo-pyrimidin-1-yl]-1-methyl-ethyl]-2-methyl-propanamide, / V-[2-[3-[2-(2-cyanoethoxy)-2-(5-fluoro-2-methoxy-phenyl)ethyl]-5-[(Z)- / \ / -isopropoxy-C-meth- yl-carbonimidoyl]-2,6-dioxo-pyrimidin-1-yl]-1-methyl-ethyl]-2-methyl-propanamide, rac-3-[3-(3-chloro-2-fluoro-phenoxy)-6-methyl-pyridazin-4-yl]-5-[(2-chloro-4-methyl-phenyl)- methyl]-5,6-dihydro-4 / 7-1 ,2,4-oxadiazine, (5S)-3-[3-(3-chloro-2-fluoro-phenoxy)-6-methyl- pyridazin-4-yl]-5-[(2-chloro-4-methyl-phenyl)methyl]-5,6-dihydro-4 / 7-1 ,2,4-oxadiazine, (5R)-3-[3-(3-chloro-2-fluoro-phenoxy)-6-methyl-pyridazin-4-yl]-5-[(2-chloro-4-methyl-phenyl)- methyl]-5,6-dihydro-4 / 7-1 ,2,4-oxadiazine, 2-(4-fluorophenoxy)-1-[4-[5-(trifluoromethyl)-

[0470] 1.2.4-oxadiazol-3-yl]phenyl]ethanone, 2-[(6-fluoro-3-pyridyl)oxy]-1-[4-[5-(trifluoromethyl)- 1 ,2,4-oxadiazol-3-yl]phenyl]ethanone, 2-(4-fluoroanilino)-1-[4-[5-(trifluoromethyl)-1 ,2,4-oxa- diazol-3-yl]phenyl]ethenone, ethyl 1-[[4-[[2-(trifluoromethyl)-1 ,3-dioxolan-2-yl]methoxy]- phenyl]methyl]-1 / 7-pyrazole-4-carboxylate, ethyl 1-[[4-[[(1 Z)-2-ethoxy-3, 3, 3-trifluoro-1 -pro- pen-1 -yl]oxy]phenyl]methyl]-1 / 7-pyrazole-4-carboxylate; BASF SE 240867W001

[0471] B19464WO

[0472] 45

[0473] The fungicides described by common names, their preparation and their activity e.g. against harmful fungi is known (cf.: http: / / www.alanwood.net / pesticides / ); these substances are commercially available.

[0474] The active substances, their preparation and their activity e.g. against fungi is known (www.bcpcpesticidecompendium.bcpc.org / ); many of them are commercially available. Compounds defined by IIIPAC nomenclature, their preparation and pesticidal activity are also known (e.g. Can. J. Plant Sci. 48(6), 587-94, 1968; EP-141 317; EP-152 031 ; EP-226 917; EP-243 970; EP-256 503; EP-428 941 ; EP-532 022; EP-1 028 125; EP-1 035 122;

[0475] EP-1 201 648; EP-1 122 244, JP2002316902; DE19650197; DE10021412; DE102005009458; US 3,296,272; US 3,325,503; WO 98 / 46608; WO 99 / 14187; WO 99 / 24413; WO 99 / 27783;

[0476] WO 00 / 29404; WO 00 / 46148; WO 00 / 65913; WO 01 / 54501; WO 01 / 56358; WO 02 / 22583;

[0477] WO 02 / 40431; WO 03 / 10149; WO 03 / 11853; WO 03 / 14103; WO 03 / 16286; WO 03 / 53145;

[0478] WO 03 / 61388; WO 03 / 66609; WO 03 / 74491; WO 04 / 49804; WO 04 / 83193; WO 05 / 120234;

[0479] WO 05 / 123689; WO 05 / 123690; WO 05 / 63721; WO 05 / 87772; WO 05 / 87773; WO 06 / 15866; WO 06 / 87325; WO 06 / 87343; WO 07 / 82098; WO 07 / 90624, WO 10 / 139271 , WO 11 / 028657, WO 12 / 168188, WO 07 / 006670, WO 11 / 77514; WO 13 / 047749, WO 10 / 069882, WO 13 / 047441 , WO 03 / 16303, WO 09 / 90181, WO 13 / 007767, WO 13 / 010862, WO 13 / 127704, WO 13 / 024009, WO 13 / 24010, WO 13 / 047441, WO 13 / 162072, WO 13 / 092224, WO 11 / 135833, CN 1907024, CN 1456054, CN 103387541, CN 1309897, WO 12 / 84812, CN 1907024, WO 09094442, WO 14 / 60177, WO 13 / 116251, WO 08 / 013622, WO 15 / 65922, WO 94 / 01546, EP 2865265, WO 07 / 129454, WO 12 / 165511, WO 11 / 081174, WO 13 / 47441, WO 16 / 156241, WO 16 / 162265, WO 23 / 99460, WO 21 / 244950, WO 21 / 244951, WO 22 / 130188, WO 22 / 243810, WO 21 / 255070, WO 21 / 176057, WO 21 / 153754, JP2023064110, JP2022153603, JP2022046550, JP2022031355, WO 22 / 249074, WO 23 / 046861, WO 18 / 177894, WO 20 / 212513, WO 20 / 097012, US 2023 / 0069915.

[0480] Some compounds are identified by their CAS Registry Number.

[0481] Biopesticides

[0482] Suitable mixing partners for the compounds of the invention also include biopesticides. Biopesticides have been defined as a form of pesticides based on micro-organisms (bacteria, fungi, viruses, nematodes, etc.) or natural products (compounds, e.g. metabolites, proteins, or extracts from biological or other natural sources) (U.S. Environmental Protection Agency: http: / / www.epa.gov / pesticides / biopesticides / ). Biopesticides fall into two major classes, microbial and biochemical pesticides:

[0483] (1) Microbial pesticides consist of bacteria, fungi or viruses (and often include the metabolites that bacteria and fungi produce). Entomopathogenic nematodes are also classified as microbial pesticides, even though they are multi-cellular.

[0484] (2) Biochemical pesticides are naturally occurring substances or or structurally-similar and functionally identical to a naturally-occurring substance and extracts from biological sources that control pests or provide other crop protection uses as defined below, but have non-toxic mode of actions (e.g. growth or developmental regulation, attractants, repellents or defence activators (e.g. induced resistance) and are relatively non-toxic to mammals.

[0485] The following list of biopesticides, in conjunction with which the compounds of the invention can be used, illustrates the possible combinations: BASF SE 240867W001

[0486] B19464WO

[0487] 46

[0488] L) Biopesticides

[0489] L1) Microbial pesticides with fungicidal, bactericidal, viricidal and / or plant defense activator activity: Ampelomyces quisqualis, Aspergillus flavus, Aureobasidium pullulans, Bacillus altitudinis, B. amyloliquefaciens, B. amyloliquefaciens ssp. plantarum (also referred to as B. velezensis), B. megaterium, B. mojavensis, B. mycoides, B. pumilus, B. simplex, B. solisalsi, B. subtil is, B. subtilis var. amyloliquefaciens, B. velezensis, Candida oleophila, C. saitoana, Clavibacter michiganensis (bacteriophages), Coniothyrium minitans, Cryphonectria parasitica, Cryptococcus albidus, Dilophosphora alopecuri, Fusarium oxysporum, Clonostachys rosea f. catenulate (also named Gliocladium catenulatum), Gliocladium roseum, Lysobacter antibioticus, L. enzymogenes, Metschnikowia fructicola, Microdochium dimerum, Microsphaeropsis ochracea, Muscodor al bus, Paenibacillus alvei, Paenibacillus epiphyticus, P. polymyxa, Pantoea vagans, Penicillium bilaiae, Phlebiopsis gigantea, Pseudomonas sp., Pseudomonas chloraphis, Pseudozyma flocculosa, Pichia anomala, Pythium oligandrum, Sphaerodes mycoparasitica, Streptomyces griseoviridis, S. lydicus, S. violaceusniger, Talaromyces flavus, Trichoderma asperelloides, T. asperellum, T. atroviride, T. fertile, T. gamsii, T. harmatum, T. harzianum, T. polysporum, T. stromaticum, T. virens, T. viride, Typhula phacorrhiza, Ulocladium oudemansii, Verticillium dahliae, zucchini yellow mosaic virus (avirulent strain);

[0490] L2) Biochemical pesticides with fungicidal, bactericidal, viricidal and / or plant defense activator activity: harpin protein, plant oils (BM3): tea tree oil, orange oil (L.2.1), eugenol, limonene (L.2.2), geraniol (L.2.3), thymol (L.2.4); Reynoutria sachalinensis extract, aureobasidin (in particular aureobasidin A (L.2.5)), ambruticin (L.2.6), bafilomycin (L.2.7) (in particular bafilomycin A1 , B1 and 01), chlorflavonin (L.2.8), cinnamaldehyde (L.2.9), natamycin (L.2.10; F8);

[0491] L3) Microbial pesticides with insecticidal, acaricidal, molluscidal and / or nematicidal activity: Agrobacterium radiobacter, Bacillus cereus, B. firmus, B. thuringiensis, B. thuringiensis ssp. aizawai, B. t. ssp. israelensis, B. t. ssp. galleriae, B. t. ssp. kurstaki, B. t. ssp. tenebrionis, Beauveria bassiana, B. brongniartii, Burkholderia spp., Chromobacterium subtsugae, Cydia pomonella granulovirus (CpGV), Cryptophlebia leucotreta granulovirus (CrleGV), Flavobacterium spp., Helicoverpa armigera nucleopolyhedrovirus (HearNPV), Helicoverpa zea nucleopolyhedrovirus (HzNPV), Helicoverpa zea single capsid nucleopolyhedrovirus (HzSNPV), Heterorhabditis bacteriophora, Isaria fumosorosea, Lecanicillium longisporum, L. muscarium, Metarhizium anisopliae, M. anisopliae var. anisopliae, M. anisopliae var. acridum, Nomuraea rileyi, Paecilomyces fumosoroseus, P. lilacinus, Paenibacillus popilliae, Pasteuria spp., P. nishizawae, P. penetrans, P. ramosa, P. thornea, P. usgae, Pseudomonas fluorescens, Spodoptera littoralis nucleopolyhedrovirus (SpliNPV), Steinernema carpocapsae, S. feltiae, S. kraussei, Streptomyces galbus, S. microflavus',

[0492] L4) Biochemical pesticides with insecticidal, acaricidal, molluscidal, pheromone and / or nematicidal activity: L-carvone, citral, (E,Z)-7,9-dodecadien-1-yl acetate, ethyl formate, (E,Z)-2,4-ethyl decadienoate (pear ester), (Z,Z,E)-7,11,13-hexadecatrienal, heptyl butyrate, isopropyl myristate, lavanulyl senecioate, cis-jasmone, 2-methyl-1 -butanol, methyl eugenol, methyl jasmonate, (E,Z)-2,13-octadecadien-1-ol, (E,Z)-2,13-octadecadien-1-ol acetate, (E,Z)-3,13-octadecadien-1-ol, (R)-1-octen-3-ol, pentatermanone, BASF SE 240867W001

[0493] B19464WO

[0494] 47

[0495] (E,Z,Z)-3,8,11-tetradecatrienyl acetate, (Z,E)-9,12-tetradecadien-1-yl acetate, (Z)-7-tetradecen-2-one, (Z)-9-tetradecen-1-yl acetate, (Z)-11-tetradecenal, (Z)-11-tetra- decen-1-ol, extract of Chenopodium ambrosiodes, Neem oil, Quillay extract;

[0496] L5) Microbial pesticides with plant stress reducing, plant growth regulator, plant growth promoting and / or yield enhancing activity: Azospirillum amazonense, A. brasilense,

[0497] A. lipoferum, A. irakense, A. halopraeferens, Bradyrhizobium spp., B. elkanii, B. japonicum,

[0498] B. liaoningense, B. lupini, Delftia acidovorans, Glomus intraradices, Mesorhizobium spp., Rhizobium leguminosarum bv. phaseoli, R. I. bv. trifolii, R. I. bv. viciae, R. tropici, Sinorhizobium meliloti.

[0499] The biopesticides from group L1) and / or L2) may also have insecticidal, acaricidal, molluscidal, pheromone, nematicidal, plant stress reducing, plant growth regulator, plant growth promoting and / or yield enhancing activity. The biopesticides from group L3) and / or L4) may also have fungicidal, bactericidal, viricidal, plant defense activator, plant stress reducing, plant growth regulator, plant growth promoting and / or yield enhancing activity. The biopesticides from group L5) may also have fungicidal, bactericidal, viricidal, plant defense activator, insecticidal, acaricidal, molluscidal, pheromone and / or nematicidal activity.

[0500] Many of these biopesticides have been deposited under deposition numbers mentioned herein (the prefices e.g. ATCC or DSM refer to the acronym of the respective culture collection, for details see e.g. here: http: / / www. wfcc.info / ccinfo / collection / by_acronym / ), are referred to in literature, registered and / or are commercially available: mixtures of Aureobasidium pullulans DSM 14940 and DSM 14941 isolated in 1989 in Konstanz, Germany (e.g. blastospores in Blossom Protect® from bio-ferm GmbH, Austria), Azospirillum brasilense Sp245 originally isolated in wheat reagion of South Brazil (Passo Fundo) at least prior to 1980 (BR 11005; e.g. GELFIX® Gramineas from BASF Agricultural Specialties Ltd., Brazil), A. brasilense strains Ab- V5 and Ab-V6 (e.g. in AzoMax from Novozymes BioAg Produtos papra Agricultura Ltda., Quattro Barras, Brazil or Simbiose-Maiz® from Simbiose-Agro, Brazil; Plant Soil 331 , 413-425, 2010), Bacillus amyloliquefaciens strain AP-188 (NRRL B-50615 and B-50331 ; US8,445,255); B. amylo-liquefaciens ssp. plantarum strains formerly also sometimes referred to as B. subtilis, recently together with B. methylotrophicus, and B. velezensis classified as B. velezensis (Int. J. Syst. Evol. Microbiol. 66, 1212-1217, 2016): B. a. ssp. plantarum or B. velezensis D747 isolated from air in Kikugawashi, Japan (US 20130236522 A1 ; FERM BP 8234; e.g. Double Nickel™ 55 WDG from Certis LLC, USA), B. a. ssp. plantarum or B. velezensis FZB24 isolated from soil in Brandenburg, Germany (also called SB3615; DSM 96-2; J. Plant Dis. Prot. 105, 181-197, 1998; e.g. Taegro® from Novozyme Biologicals, Inc., USA), B. a. ssp. plantarum or B. velezensis FZB42 isolated from soil in Brandenburg, Germany (DSM 23117; J. Plant Dis. Prot. 105, 181-197, 1998; e.g. RhizoVital® 42 from AbiTEP GmbH, Germany), B. a. ssp. plantarum or B. vele-zensis MBI600 isolated from faba bean in Sutton Bonington, Nottinghamshire, U.K. at least before 1988 (also called 1430; NRRL B 50595; US 2012 / 0149571 A1; e.g. Integral® from BASF Corp., USA), B. a. ssp. plantarum or B. velezensis QST-713 isolated from peach orchard in 1995 in California, U.S.A. (NRRL B 21661 ; e.g. Serenade® MAX from Bayer Crop Science LP, USA), B. a. ssp. plantarum or B. velezensis TJ1000 isolated in 1992 in South Dakoda, U.S.A, (also called 1BE; ATCC BAA-390; CA 2471555 A1 ; e.g. QuickRoots™ from TJ Technologies, Watertown, SD, USA); B. firmus CNCM 1-1582, a variant of parental strain EIP- N1 (CNCM 1-1556) isolated from soil of central plain area of Israel (WO 2009 / 126473, BASF SE 240867W001

[0501] B19464WO

[0502] 48

[0503] US6,406,690; e.g. Votivo® from Bayer CropScience LP, USA), B. pumilus GHA 180 isolated from apple tree rhizo-sphere in Mexico (IDAC 260707-01; e.g. PRO-MIX® BX from Premier Horticulture, Quebec, Canada), B. pumilus INR-7 otherwise referred to as BU F22 and BU-F33 isolated at least be-fore 1993 from cucumber infested by Erwinia tracheiphila (NRRL B-50185, NRRL B-50153; US 8,445,255), B. pumilus KFP9F isolated from the rhizosphere of grasses in South Africa at least before 2008 (NRRL B-50754; WO 2014 / 029697; e.g. BAC-UP or FUSION- P from BASF Agricultural Specialities (Pty) Ltd., South Africa), B. pumilus QST 2808 was isolated from soil collected in Pohnpei, Federated States of Micronesia, in 1998 (NRRL B 30087; e.g. Sonata® or Ballad® Plus from Bayer Crop Science LP, USA), B. simplex ABU 288 (NRRL B-50304; US8,445,255), B. subtilis FB17 also called UD 1022 or UD10-22 isolated from red beet roots in North America (ATCC PTA-11857; System. Appl. Microbiol. 27, 372-379, 2004; US2010 / 0260735; WO 2011 / 109395); B. thuringiensis ssp. aizawai ABTS-1857 isolated from soil taken from a lawn in Ephraim, Wisconsin, U.S.A., in 1987 (also called ABG 6346; ATCC SD-1372; e.g. XenTari® from BioFa AG, Munsingen, Germany), B. t. ssp. kurstaki ABTS- 351 identical to HD-1 isolated in 1967 from diseased Pink Bollworm black larvae in Brownsville, Texas, U.S.A. (ATCC SD-1275; e.g. Dipel® DF from Valent BioSciences, IL, USA), B. t. ssp. kurstaki SB4 isolated from E. saccharina larval cadavers (NRRL B-50753; e.g. Beta Pro® from BASF Agricultural Specialities (Pty) Ltd., South Africa), B. t. ssp. tenebrionis NB-176-1 , a mutant of strain NB-125, a wild type strain isolated in 1982 from a dead pupa of the beetle Tenebrio molitor (DSM 5480; EP 585215 B1; e.g. Novodor® from Valent BioSciences, Switzerland), Beauveria bassiana GHA (ATCC 74250; e.g. BotaniGard® 22WGP from Laverlam Int. Corp., USA), B. bassiana JW-1 (ATCC 74040; e.g. Naturalis® from CBC (Europe) S.r.l., Italy), B. bassiana PPRI 5339 isolated from the larva of the tortoise beetle Conchyloctenia punctata (NRRL 50757; e.g. Broad Band® from BASF Agricultural Specialities (Pty) Ltd., South Africa), Bradyrhizobium elkanii strains SEMIA 5019 (also called 29W) isolated in Rio de Janeiro, Brazil and SEMIA 587 isolated in 1967 in the State of Rio Grande do Sul, from an area previously inoculated with a North American isolate, and used in commercial inoculants since 1968 (Appl. Environ. Microbiol. 73(8), 2635, 2007; e.g. GELFIX 5 from BASF Agricultural Specialties Ltd., Brazil), B. japonicum 532c isolated from Wisconsin field in U.S.A. (Nitragin 61A152; Can. J. Plant. Sci. 70, 661-666, 1990; e.g. in Rhizoflo®, Histick®, Hicoat® Super from BASF Agricultural Specialties Ltd., Canada), B. japonicum E-109 variant of strain USDA 138 (INTA E109, SEMIA 5085; Eur. J. Soil Biol. 45, 28-35, 2009; Biol. Fertil. Soils 47, 81-89, 2011); B. japonicum strains deposited at SEMIA known from Appl. Environ. Microbiol. 73(8), 2635, 2007: SEMIA 5079 isolated from soil in Cerrados region, Brazil by Embrapa-Cerrados used in commercial inoculants since 1992 (CPAC 15; e.g. GELFIX 5 or ADHERE 60 from BASF Agricultural Specialties Ltd., Brazil), B. japonicum SEMIA 5080 obtained under lab conditions by Embrapa-Cerrados in Brazil and used in commercial inoculants since 1992, being a natural variant of SEMIA 586 (CB1809) originally isolated in U.S.A. (CPAC 7; e.g. GELFIX 5 or ADHERE 60 from BASF Agricultural Specialties Ltd., Brazil); Burkholderia sp. A396 isolated from soil in Nikko, Japan, in 2008 (NRRL B-50319; WO 2013 / 032693; Marrone Bio Innovations, Inc., USA), Coniothyrium minitans CON / M / 91-08 isolated from oilseed rape (WO 1996 / 021358; DSM 9660; e.g. Contans® WG, Intercept® WG from Bayer CropScience AG, Germany), harpin (alpha-beta) protein (Science 257, 85-88, 1992; e.g. Messenger™ or HARP-N Tek from Plant Health Care pic, U.K.), Helicoverpa armigera nucleopolyhedrovirus (HearNPV) (J. Invertebrate BASF SE 240867W001

[0504] B19464WO

[0505] 49

[0506] Pathol. 107, 112-126, 2011 ; e.g. Helicovex® from Adermatt Biocontrol, Switzerland;

[0507] Diplomata® from Koppert, Brazil; Vivus® Max from AgBiTech Pty Ltd., Queensland, Australia), Helicoverpa zea single capsid nucleopolyhedrovirus (HzSNPV) (e.g. Gemstar® from Certis LLC, USA), Helicoverpa zea nucleopolyhedrovirus ABA-NPV-U (e.g. Heligen® from AgBiTech Pty Ltd., Queensland, Australia), Heterorhabditis bacteriophora (e.g. Nemasys® G from BASF Agricultural Specialities Limited, UK), Isaria fumosorosea Apopka-97 isolated from mealy bug on gynura in Apopka, Florida, U.S.A. (ATCC 20874; Biocontrol Science Technol. 22(7), 747- 761 , 2012; e.g. PFR-97™ or PreFeRal® from Certis LLC, USA), Metarhizium anisopliae var. anisopliae F52 also called 275 or V275 isolated from codling moth in Austria (DSM 3884, ATCC 90448; e.g. Met52® Novozymes Biologicals BioAg Group, Canada), Metschnikowia fructicola 277 isolated from grapes in the central part of Israel (US 6,994,849; NRRL Y-30752; e.g. formerly Shemer® from Agrogreen, Israel), Paecilomyces ilacinus 251 isolated from infected nematode eggs in the Philippines (AGAL 89 / 030550; WQ1991 / 02051 ; Crop Protection 27, 352- 361 , 2008; e.g. BioAct®from Bayer CropScience AG, Germany and MeloCon® from Certis, USA), Paenibacillus alvei NAS6G6 isolated from the rhizosphere of grasses in South Africa at least before 2008 (WO 2014 / 029697; NRRL B-50755; e.g. BAC-UP from BASF Agricultural Specialities (Pty) Ltd., South Africa), Paenibacillus strains isolated from soil samples from a variety of European locations including Germany: P. epiphyticus Lu17015 (WO 2016 / 020371 ; DSM 26971), P. polymyxa ssp. plantarum Lu16774 (WO 2016 / 020371 ; DSM 26969), P. p. ssp. plantarum strain Lu17007 (WO 2016 / 020371 ; DSM 26970); Pasteuria nishizawae Pn1 isolated from a soybean field in the mid-2000s in Illinois, U.S.A. (ATCC SD 5833; Federal Register 76(22), 5808, February 2, 2011 ; e.g. Clariva™ PN from Syngenta Crop Protection, LLC, USA), Penicillium bilaiae (also called P. bilaii) strains ATCC 18309 (= ATCC 74319), ATCC 20851 and / or ATCC 22348 (=ATCC 74318) originally isolated from soil in Alberta, Canada (Fertilizer Res. 39, 97-103, 1994; Can. J. Plant Sci. 78(1), 91-102, 1998; US 5,026,417, WO 1995 / 017806; e.g. Jump Start®, Provide® from Novozymes Biologicals BioAg Group, Canada), Reynoutria sachalinensis extract (EP 0307510 B1 ; e.g. Regalia® SC from Marrone BioInnovations, Davis, CA, USA or Milsana® from BioFa AG, Germany), Steinernema carpocapsae (e.g. Millenium® from BASF Agricultural Specialities Limited, UK), S. feltiae (e.g. Nemashield® from BioWorks, Inc., USA; Nemasys® from BASF Agricultural Specialities Limited, UK), Streptomyces microflavus NRRL B-50550 (WO 2014 / 124369; Bayer CropScience, Germany), Trichoderma asperelloides JM41 R isolated in South Africa (NRRL 50759; also referred to as T. fertile; e.g. Trichoplus® from BASF Agricultural Specialities (Pty) Ltd., South Africa), T. harzianum T-22 also called KRL-AG2 (ATCC 20847; BioControl 57, 687-696, 2012; e.g. Plantshield® from BioWorks Inc., USA or SabrEx™ from Advanced Biological Marketing Inc., Van Wert, OH, USA).

[0508] According to the invention, the solid material (dry matter) of the biopesticides (with the exception of oils e.g. Neem oil) are considered as active components (e.g. to be obtained after drying or evaporation of the extraction or suspension medium in case of liquid formulations of the microbial pesticides).

[0509] In accordance with the invention, the weight ratios and percentages used herein for a biological extract e.g. Quillay extract are based on the total weight of the dry content (solid material) of the respective extract(s). BASF SE 240867W001

[0510] B19464WO

[0511] 50

[0512] The total weight ratios of compositions comprising at least one microbial pesticide in the form of viable microbial cells including dormant forms, can be determined using the amount of CFU of the respective microorganism to calculate the total weight of the respective active component with the following equation that 1x1010CFU equals one gram of total weight of the respective active component. Colony forming unit is measure of viable microbial cells, in particular fungal and bacterial cells. In addition, here “CFU” may also be understood as the number of (juvenile) individual nematodes in case of (entomopathogenic) nematode biopesticides, e.g. Steinernema feltiae.

[0513] When mixtures comprising microbial pesticides are employed in crop protection, the application rates range from 1x106to 5x1016(or more) CFU / ha, preferably from 1x108to 1x1013CFU / ha, and even more preferably from 1x109to 5x1015CFU / ha and in particular from 1x1012to 5x1014CFU / ha. In the case of nematodes as microbial pesticides (e.g. Steinernema feltiae), the application rates regularly range from 1x105to 1x1012(or more), preferably from 1x108to 1x1011, more preferably from 5x108to 1x101° individuals (e.g. in the form of eggs, juvenile or any other live stages, preferably in an infetive juvenile stage) per ha.

[0514] When mixtures comprising microbial pesticides are employed in seed treatment, the application rates generally range from 1x106to 1x1012(or more) CFU / seed, preferably from 1x106to 1x109CFU / seed. Furthermore, the application rates with respect to seed treatment generally range from 1x107to 1x1014(or more) CFU per 100 kg of seed, preferably from 1x109to 1x1012CFU per 100 kg of seed.

[0515] Formulations

[0516] The invention also relates to agrochemical compositions comprising an auxiliary and at least one compound of the invention or a mixture thereof.

[0517] An agrochemical composition comprises a pesticidally effective amount of a compound of the invention or a mixture thereof.

[0518] The compounds of the invention or the mixtures thereof can be converted into customary types of agro-chemical compositions, e.g. solutions, emulsions, suspensions, dusts, powders, pastes, granules, pressings, capsules, and mixtures thereof. Examples for composition types are suspensions (e.g. SC, OD, FS), emulsifiable concentrates (e.g. EC), emulsions (e.g. EW, EO, ES, ME), capsules (e.g. CS, ZC), pastes, pastilles, wettable powders or dusts (e.g. WP, SP, WS, DP, DS), pressings (e.g. BR, TB, DT), granules (e.g. WG, SG, GR, FG, GG, MG), insecticidal articles (e.g. LN), as well as gel formulations for the treatment of plant propagation materials e.g. seeds (e.g. GF). These and further compositions types are defined in the “Catalogue of pesticide formulation types and international coding system”, Technical Monograph No. 2, 6th Ed. May 2008, CropLife International.

[0519] The compositions are prepared in a known manner, e.g. described by Mollet and Grubemann, Formulation technology, Wiley VCH, Weinheim, 2001 ; or Knowles, New developments in crop protection product formulation, Agrow Reports DS243, T&F Informa, London, 2005.

[0520] Examples for suitable auxiliaries are solvents, liquid carriers, solid carriers or fillers, surfactants, dispersants, emulsifiers, wetters, adjuvants, solubilizers, penetration enhancers, protective colloids, adhesion agents, thickeners, humectants, repellents, attractants, feeding stimulants, compatibilizers, bactericides, anti-freezing agents, anti-foaming agents, colorants, tackifiers and binders. BASF SE 240867W001

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[0522] 51

[0523] Suitable solvents and liquid carriers are water and organic solvents, e.g. mineral oil fractions of medium to high boiling point, e.g. kerosene, diesel oil; oils of vegetable or animal origin; hydrocarbons, e.g. toluene, paraffin, tetrahydronaphthalene, alkylated naphthalenes; alcohols, e.g. ethanol, propanol, butanol, benzylalcohol, cyclohexanol; glycols; DMSO; ketones, e.g. cyclohexanone; esters, e.g. lactates, carbonates, fatty acid esters, gamma-butyrolactone; fatty acids; phosphonates; amines; amides, e.g. N-methylpyrrolidone, fatty acid dimethylamides; and mixtures thereof.

[0524] Suitable solid carriers or fillers are mineral earths, e.g. silicates, silica gels, talc, kaolins, limestone, lime, chalk, clays, dolomite, diatomaceous earth, bentonite, CaSC>4, MgSCU, MgO; polysaccharide powders, e.g. cellulose, starch; fertilizers, e.g. (NH^SOt, (NH4)3PO4, NH4NO3, ureas; products of vegetable origin, e.g. cereal meal, tree bark meal, wood meal, nutshell meal, and mixtures thereof.

[0525] Suitable surfactants are surface-active compounds, e.g. anionic, cationic, nonionic and amphoteric surfactants, block polymers, polyelectrolytes, and mixtures thereof. Such surfactants can be used as emusifier, dispersant, solubilizer, wetter, penetration enhancer, protective colloid, or adjuvant. Examples of surfactants are listed in McCutcheon’s, Vol.1: Emulsifiers & Detergents, McCutcheon’s Directories, Glen Rock, USA, 2008 (International or North American Ed.).

[0526] Suitable anionic surfactants are alkali, alkaline earth or ammonium salts of sulfonates, sulfates, phosphates, carboxylates, and mixtures thereof. Examples of sulfonates are alkylarylsulfonates, diphenylsulfonates, alpha-olefin sulfonates, lignine sulfonates, sulfonates of fatty acids and oils, sulfonates of ethoxylated alkylphenols, sulfonates of alkoxylated arylphenols, sulfonates of condensed naphthalenes, sulfonates of dodecyl- and tridecylbenzenes, sulfonates of naphthalenes and alkylnaphthalenes, sulfosuccinates or sulfosuccinamates. Examples of sulfates are sulfates of fatty acids and oils, of ethoxylated alkylphenols, of alcohols, of ethoxylated alcohols, or of fatty acid esters. Examples of phosphates are phosphate esters. Examples of carboxylates are alkyl carboxylates, and carboxylated alcohol or alkylphenol ethoxylates.

[0527] Suitable nonionic surfactants are alkoxylates, N-subsituted fatty acid amides, amine oxides, esters, sugar-based surfactants, polymeric surfactants, and mixtures thereof. Examples of alkoxylates are compounds e.g. alcohols, alkylphenols, amines, amides, arylphenols, fatty acids or fatty acid esters which have been alkoxylated with 1 to 50 equivalents. Ethylene oxide and / or propylene oxide may be employed for the alkoxylation, preferably ethylene oxide. Examples of N-subsititued fatty acid amides are fatty acid glucamides or fatty acid alkanola-mides. Examples of esters are fatty acid esters, glycerol esters or monoglycerides. Examples of sugar-based surfactants are sorbitans, ethoxylated sorbitans, sucrose and glucose esters or alkylpolyglucosides. Examples of polymeric surfactants are homo- or copolymers of vinylpyrrolidone, vinylalcohols, or vinylacetate.

[0528] Suitable cationic surfactants are quaternary surfactants, e.g. quaternary ammonium compounds with one or two hydrophobic groups, or salts of long-chain primary amines. Suitable amphoteric surfactants are alkylbetains and imidazolines. Suitable block polymers are block polymers of the A-B or A-B-A type comprising blocks of polyethylene oxide and polypropylene oxide, or of the A- B-C type comprising alkanol, polyethylene oxide and polypropylene oxide. Suitable polyelectrolytes are polyacids or polybases. Examples of polyacids are alkali salts of polyacrylic BASF SE 240867W001

[0529] B19464WO

[0530] 52 acid or polyacid comb polymers. Examples of polybases are polyvinylamines, or polyethyleneamines.

[0531] Suitable adjuvants are compounds, which have a neglectable or even no pesticidal activity themselves, and which improve the biological performance of the compounds of the invention on the target. Examples are surfactants, mineral or vegetable oils, and other auxilaries. Further examples are listed by Knowles, Adjuvants and additives, Agrow Reports DS256, T&F Informa UK, 2006, chapter 5.

[0532] Suitable thickeners are polysaccharides (e.g. xanthan gum, carboxymethylcellulose), anorganic clays (organically modified or unmodified), polycarboxylates, and silicates.

[0533] Suitable bactericides are bronopol and isothiazolinone derivatives e.g. alkylisothiazolinones and benzisothiazolinones.

[0534] Suitable anti-freezing agents are ethylene glycol, propylene glycol, urea, and glycerin. Suitable anti-foaming agents are silicones, long chain alcohols, and salts of fatty acids.

[0535] Suitable colorants (e.g. in red, blue, or green) are pigments of low water solubility and water- soluble dyes. Examples are inorganic colorants (e.g. iron oxide, titan oxide, iron hexacyanoferrate) and organic colorants (e.g. alizarin-, azo-, and phthalocyanine colorants). Suitable tackifiers or binders are polyvinylpyrrolidons, polyvinylacetates, polyvinyl alcohols, polyacrylates, biological or synthetic waxes, and cellulose ethers.

[0536] Examples for composition types and their preparation are: i) Water-soluble concentrates (SL, LS)

[0537] 10-60 wt% of a compound I according to the invention and 5-15 wt% wetting agent (e.g. alcohol alkoxylates) are dissolved in water and / or in a water-soluble solvent (e.g. alcohols) up to 100 wt%. The active substance dissolves upon dilution with water. ii) Dispersible concentrates (DC)

[0538] 5-25 wt% of a compound I according to the invention and 1-10 wt% dispersant (e.g. polyvinylpyrrolidone) are dissolved in up to 100 wt% organic solvent (e.g. cyclohexanone). Dilution with water gives a dispersion. iii) Emulsifiable concentrates (EC)

[0539] 15-70 wt% of a compound I according to the invention and 5-10 wt% emulsifiers (e.g. calcium dodecylbenzenesulfonate and castor oil ethoxylate) are dissolved in up to 100 wt% waterinsoluble organic solvent (e.g. aromatic hydrocarbon). Dilution with water gives an emulsion. iv) Emulsions (EW, EO, ES)

[0540] 5-40 wt% of a compound I according to the invention and 1-10 wt% emulsifiers (e.g. calcium dodecylbenzenesulfonate and castor oil ethoxylate) are dissolved in 20-40 wt% water-insoluble organic solvent (e.g. aromatic hydrocarbon). This mixture is introduced into up to 100 wt% water by means of an emulsifying machine and made into a homogeneous emulsion. Dilution with water gives an emulsion. v) Suspensions (SC, OD, FS)

[0541] In an agitated ball mill, 20-60 wt% of a compound I according to the invention are comminuted with addition of 2-10 wt% dispersants and wetting agents (e.g. sodium lignosulfonate and alcohol ethoxylate), 0,1-2 wt% thickener (e.g. xanthan gum) and up to 100 wt% water to give a fine active substance suspension. Dilution with water gives a stable suspension of the active sub-stance. For FS type composition up to 40 wt% binder (e.g. polyvinylalcohol) is added. vi) Water-dispersible granules and water-soluble granules (WG, SG) BASF SE 240867W001

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[0544] 50-80 wt% of a compound I according to the invention are ground finely with addition of up to 100 wt% dispersants and wetting agents (e.g. sodium lignosulfonate and alcohol ethoxylate) and prepared as water-dispersible or water-soluble granules by means of technical appliances (e.g. extrusion, spray tower, fluidized bed). Dilution with water gives a stable dispersion or solution of the active substance. vii) Water-dispersible powders and water-soluble powders (WP, SP, WS)

[0545] 50-80 wt% of a compound I according to the invention are ground in a rotor-stator mill with addition of 1-5 wt% dispersants (e.g. sodium lignosulfonate), 1-3 wt% wetting agents (e.g. alcohol ethoxylate) and up to 100 wt% solid carrier, e.g. silica gel. Dilution with water gives a stable dispersion or solution of the active substance. viii) Gel (GW, GF)

[0546] In an agitated ball mill, 5-25 wt% of a compound I according to the invention are comminuted with addition of 3-10 wt% dispersants (e.g. sodium lignosulfonate), 1-5 wt% thickener (e.g. carboxymethylcellulose) and up to 100 wt% water to give a fine suspension of the active substance. Dilution with water gives a stable suspension of the active substance. ix) Microemulsion (ME)

[0547] 5-20 wt% of a compound I according to the invention are added to 5-30 wt% organic solvent blend (e.g. fatty acid dimethylamide and cyclohexanone), 10-25 wt% surfactant blend (e.g. alcohol ethoxylate and arylphenol ethoxylate), and water up to 100 %. This mixture is stirred for 1 h to produce spontaneously a thermodynamically stable microemulsion. x) Microcapsules (CS)

[0548] An oil phase comprising 5-50 wt% of a compound I according to the invention, 0-40 wt% water insoluble organic solvent (e.g. aromatic hydrocarbon), 2-15 wt% acrylic monomers (e.g. methylmethacrylate, methacrylic acid and a di- or triacrylate) are dispersed into an aqueous solution of a protective colloid (e.g. polyvinyl alcohol). Radical polymerization initiated by a radical initiator results in the formation of poly(meth)acrylate microcapsules. Alternatively, an oil phase comprising 5-50 wt% of a compound I according to the invention, 0-40 wt% water insoluble organic solvent (e.g. aromatic hydrocarbon), and an isocyanate monomer (e.g. di- phenylme-thene-4,4’-diisocyanatae) are dispersed into an aqueous solution of a protective colloid (e.g. polyvinyl alcohol). The addition of a polyamine (e.g. hexamethylenediamine) results in the formation of a polyurea microcapsule. The monomers amount to 1-10 wt%. The wt% relate to the total CS composition. xi) Dustable powders (DP, DS)

[0549] 1-10 wt% of a compound I according to the invention are ground finely and mixed intimately with up to 100 wt% solid carrier, e.g. finely divided kaolin. xii) Granules (GR, FG)

[0550] 0.5-30 wt% of a compound I according to the invention is ground finely and associated with up to 100 wt% solid carrier (e.g. silicate). Granulation is achieved by extrusion, spray-drying or the fluidized bed. xiii) Ultra-low volume liquids (UL)

[0551] 1-50 wt% of a compound I according to the invention are dissolved in up to 100 wt% organic solvent, e.g. aromatic hydrocarbon. BASF SE 240867W001

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[0554] The compositions types i) to xi) may optionally comprise further auxiliaries, e.g. 0.1-1 wt% bactericides, 5-15 wt% anti-freezing agents, 0.1-1 wt% anti-foaming agents, and 0.1-1 wt% colorants.

[0555] The agrochemical compositions generally comprise between 0.01 and 95%, preferably between 0.1 and 90%, and most preferably between 0.5 and 75%, by weight of active substance. The active substances are employed in a purity of from 90% to 100%, preferably from 95% to 100% (according to NMR spectrum).

[0556] Various types of oils, wetters, adjuvants, fertilizer, or micronutrients, and other pesticides (e.g. herbicides, insecticides, fungicides, growth regulators, safeners) may be added to the active substances or the compositions comprising them as premix or, if appropriate not until immediately prior to use (tank mix). These agents can be admixed with the compositions according to the invention in a weight ratio of 1:100 to 100:1 , preferably 1:10 to 10:1.

[0557] The user applies the composition according to the invention usually from a predosage device, a knapsack sprayer, a spray tank, a spray plane, or an irrigation system. Usually, the agrochemical composition is made up with water, buffer, and / or further auxiliaries to the desired application concentration and the ready-to-use spray liquor or the agrochemical composition according to the invention is thus obtained. Usually, 20 to 2000 liters, preferably 50 to 400 liters, of the ready-to-use spray liquor are applied per hectare of agricultural useful area.

[0558] According to one embodiment, individual components of the composition of the invention e.g. parts of a kit or parts of a binary or ternary mixture may be mixed by the user himself in a spray tank and further auxiliaries may be added, if appropriate.

[0559] In a further embodiment, either individual components of the composition according to the invention or partially premixed components, e.g. components comprising compounds of the invention and / or mixing partners as defined above, may be mixed by the user in a spray tank and further auxiliaries and additives may be added.

[0560] In a further embodiment, either individual components of the composition according to the invention or partially premixed components, e.g. components comprising compounds of the invention and / or mixing partners as defined above, can be applied jointly (e.g. after tank mix) or consecutively.

[0561] Application methods

[0562] The compounds of the invention are suitable for use in protecting crops, plants, plant propagation materials, e.g. seeds, or soil or water, in which the plants are growing, from attack or infestation by animal pests. Therefore, the invention also relates to a plant protection method, which comprises contacting crops, plants, plant propagation materials, e.g. seeds, or soil or water, in which the plants are growing, to be protected from attack or infestation by animal pests, with a pesticidally effective amount of a compound of the invention.

[0563] The compounds of the invention are also suitable for use in combating or controlling animal pests. Therefore, the invention also relates to a method of combating or controlling animal pests, which comprises contacting the animal pests, their habitat, breeding ground, or food supply, or the crops, plants, plant propagation materials, e.g. seeds, or soil, or the area, material or environment in which the animal pests are growing or may grow, with a pesticidally effective amount of a compound of the invention. BASF SE 240867W001

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[0566] The compounds of the invention are effective through both contact and ingestion. Further-more, the compounds of the invention can be applied to any and all developmental stages, e.g. egg, larva, pupa, and adult.

[0567] The compounds of the invention can be applied as such or in form of compositions comprising them as defined above. Furthermore, the compounds of the invention can be applied together with a mixing partner or in form of compositions comprising said mixtures. The components of said mixture can be applied simultaneously, jointly or separately, or in succession, that is immediately one after another and thereby creating the mixture “in situ” on the desired location, e.g. the plant, the sequence, in the case of separate application, generally not having any effect on the result of the control measures.

[0568] The application can be carried out both before and after the infestation of the crops, plants, plant propagation materials, e.g. seeds, soil, or the area, material or environment by the pests. Suitable application methods include i.a. soil treatment, seed treatment, in furrow application, and foliar application. Soil treatment methods include drenching the soil, drip irrigation (drip application onto the soil), dipping roots, tubers or bulbs, or soil injection. Seed treatment techniques include seed dressing, seed coating, seed dusting, seed soaking, and seed pelleting. In furrow applications typically include the steps of making a furrow in cultivated land, seeding the furrow with seeds, applying the pesticidally active compound to the furrow, and closing the furrow. Foliar application refers to the application of the pesticidally active compound to plant foliage, e.g. through spray equipment. For foliar applications, it can be advantageous to modify the behavior of the pests by use of pheromones in combination with the compounds of the invention. Suitable pheromones for specific crops and pests are known and publicly available from databases of pheromones and semiochemicals, e.g. http: / / www.pherobase.com. As used herein, the term "contacting" includes both direct contact (applying the com- pounds / compositions directly on the animal pest or plant - typically to the foliage, stem or roots of the plant) and indirect contact (applying the compounds / compositions to the locus, i.e. habitat, breeding ground, plant, seed, soil, area, material, or environment in which a pest is growing or may grow, of the animal pest or plant).

[0569] The term “animal pest” includes arthropods, gastropods, and nematodes. Preferred animal pests according to the invention are arthropods, preferably insects and arachnids, in particular insects. Insects, which are of particular relevance for crops, are typically referred to as crop insect pests.

[0570] The term "crop" refers to both, growing and harvested crops.

[0571] The term “plant” includes cereals, e.g. durum and other wheat, rye, barley, triticale, oats, rice, or maize (fodder maize and sugar maize I sweet and field corn); beet, e.g. sugar beet, or fodder beet; fruits, e.g. pomes, stone fruits, or soft fruits, e.g. apples, pears, plums, peaches, nectarines, almonds, cherries, papayas, strawberries, raspberries, blackberries or gooseberries; leguminous plants, e.g. beans, lentils, peas, alfalfa, or soybeans; oil plants, e.g. rapeseed (oilseed rape), turnip rape, mustard, olives, sunflowers, coconut, cocoa beans, castor oil plants, oil palms, ground nuts, or soybeans; cucurbits, e.g. squashes, pumpkins, cucumber or melons; fiber plants, e.g. cotton, flax, hemp, or jute; citrus fruit, e.g. oranges, lemons, grapefruits or mandarins; vegetables, e.g. eggplant, spinach, lettuce (e.g. iceberg lettuce), chicory, cabbage, asparagus, cabbages, carrots, onions, garlic, leeks, tomatoes, potatoes, cucurbits or sweet peppers; lauraceous plants, e.g. avocados, cinnamon, or camphor; energy and raw material BASF SE 240867W001

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[0573] 56 plants, e.g. corn, soybean, rapeseed, sugar cane or oil palm; tobacco; nuts, e.g. walnuts; pistachios; coffee; tea; bananas; vines; hop; sweet leaf (Stevia); natural rubber plants or ornamental and forestry plants, shrubs, broad-leaved trees or evergreens, eucalyptus; turf; lawn; grass. Preferred plants include potatoes sugar beets, tobacco, wheat, rye, barley, oats, rice, corn, cotton, soybeans, rapeseed, legumes, sunflowers, coffee, or sugar cane; fruits; vines; ornamentals; or vegetables, e.g. cucumbers, tomatoes, beans or squashes.

[0574] The term "cultivated plants" is to be understood as including plants which have been modified by mutagenesis or genetic engineering in order to provide a new trait to a plant or to modify an already present trait.

[0575] Mutagenesis includes techniques of random mutagenesis using X-rays or mutagenic chemicals, but also techniques of targeted mutagenesis, in order to create mutations at a specific locus of a plant genome. Targeted mutagenesis techniques frequently use oligonucleotides or proteins like CRISPR / Cas, zinc-finger nucleases, TALENs or meganucleases to achieve the targeting effect. Genetic engineering usually uses recombinant DNA techniques to create modifications in a plant genome which under natural circumstances cannot readily be obtained by cross breeding, mutagenesis or natural recombination. Typically, one or more genes are integrated into the genome of a plant in order to add a trait or improve a trait. These integrated genes are also referred to as transgenes in the art, while plant comprising such transgenes are referred to as transgenic plants. The process of plant transformation usually produces several transformation events, which differ in the genomic locus in which a transgene has been integrated. Plants comprising a specific transgene on a specific genomic locus are usually described as comprising a specific “event”, which is referred to by a specific event name. Traits which have been introduced in plants or have been modified include in particular herbicide tolerance, insect resistance, increased yield and tolerance to abiotic conditions, like drought.

[0576] Herbicide tolerance has been created by using mutagenesis as well as using genetic engineering. Plants which have been rendered tolerant to ALS inhibitor herbicides by conventional methods of mutagenesis and breeding comprise plant varieties commercially available under the name Clearfield®.

[0577] Herbicide tolerance has been created to glyphosate, glufosinate, 2,4-D, dicamba, oxynil herbicides, like bromoxynil and ioxynil, sulfonylurea herbicides, ALS inhibitor herbicides and HPPD inhibitors, like isoxaflutole and mesotrione.

[0578] Transgenes which have been used to provide herbicide tolerance traits comprise: for tolerance to glyphosate: cp4 epsps, epsps grg23ace5, mepsps, 2mepsps, gat4601, gat4621 and goxv247, for tolerance to glufosinate: pat and bar, for tolerance to 2,4-D: aad-1 and aad-12, for tolerance to dicamba: dmo, for tolerance to oxynil herbicies: bxn, for tolerance to sulfonylurea herbicides: zm-hra, csr1-2, gm-hra, S4-HrA, for tolerance to ALS inhibitor herbicides: csr1-2, for tolerance to HPPD inhibitor herbicides: hppdPF, W336 and avhppd-03.

[0579] Transgenic corn events comprising herbicide tolerance genes are e.g., but not excluding others, DAS40278, MON801 , MON802, MON809, MON810, MON832, MON87411, MON87419, MON87427, MON88017, MON89034, NK603, GA21, MZHGOJG, HCEM485, VCO-01981-5, 676, 678, 680, 33121 , 4114, 59122, 98140, Bt10, Bt176, CBH-351, DBT418, DLL25, MS3, MS6, MZIR098, T25, TC1507 and TC6275.

[0580] Transgenic soybean events comprising herbicide tolerance genes are e.g., but not excluding others, GTS 40-3-2, MON87705, MON87708, MON87712, MON87769, MON89788, A2704-12, BASF SE 240867W001

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[0583] A2704-21, A5547-127, A5547-35, DP356043, DAS44406-6, DAS68416-4, DAS-81419-2, GU262, SYHT0H2, W62, W98, FG72 and CV127.

[0584] Transgenic cotton events comprising herbicide tolerance genes are e.g., but not excluding others, 19-51 a, 31707, 42317, 81910, 281-24-236, 3006-210-23, BXN 10211, BXN10215, BXN10222, BXN10224, MON1445, MON1698, MON88701 , MON88913, GHB119, GHB614, LLCotton25, T303-3 and T304-40.

[0585] Transgenic canola events comprising herbicide tolerance genes are e.g., but not excluding others, MON88302, HCR-1, HCN10, HCN28, HCN92, MS1, MS8, PHY14, PHY23, PHY35, PHY36, RF1 , RF2 and RF3.

[0586] Insect resistance has mainly been created by transferring bacterial genes for insecticidal proteins to plants. Transgenes which have most frequently been used are toxin genes of Bacillus spec, and synthetic variants thereof, like cry1A, crylAb, cry1Ab-Ac, crylAc, cry1A.1O5, cry1F, cry1 Fa2, cry2Ab2, cry2Ae, mcry3A, ecry3.1Ab, cry3Bb1, cry34Ab1 , cry35Ab1, cry9C, vip3A(a), vip3Aa20. However, also genes of plant origin have been transferred to other plants. In particular genes coding for protease inhibitors, like CpTI and pinll. A further approach uses transgenes in order to produce double stranded RNA in plants to target and downregulate insect genes. An example for such a transgene is dvsnf7.

[0587] Transgenic corn events comprising genes for insecticidal proteins or double stranded RNA are e.g., but not excluding others, Bt10, Bt11 , Bt176, MON801, MON802, MON809, MON810, MON863, MON87411 , MON88017, MON89034, 33121, 4114, 5307, 59122, TC1507, TC6275, CBH-351 , MIR162, DBT418 and MZIR098.

[0588] Transgenic soybean events comprising genes for insecticidal proteins are e.g., but not excluding others, MON87701, MON87751 and DAS-81419.

[0589] Transgenic cotton events comprising genes for insecticidal proteins are e.g., but not excluding others, SGK321, MON531, MON757, MON1076, MON15985, 31707, 31803, 31807, 31808, 42317, BNLA-601 , Eventl , COT67B, COT102, T303-3, T304-40, GFM Cry1A, GK12, MLS 9124, 281-24-236, 3006-210-23, GHB119 and SGK321.

[0590] Increased yield has been created by increasing ear biomass using the transgene athb17, be-ing present in corn event MON87403, or by enhancing photosynthesis using the transgene bbx32, being present in the soybean event MON87712.

[0591] Cultivated plants comprising a modified oil content have been created by using the transgenes: gm-fad2-1 , Pj.D6D, Nc.Fad3, fad2-1A and fatb1-A. Soybean events comprising at least one of these genes are: 260-05, MON87705 and MON87769.

[0592] Tolerance to abiotic conditions, in particular to tolerance to drought, has been created by using the transgene cspB, comprised by the corn event MON87460 and by using the transgene Hahb- 4, comprised by soybean event IND-00410-5.

[0593] Traits are frequently combined by combining genes in a transformation event or by combining different events during the breeding process. Preferred combination of traits are herbicide tolerance to different groups of herbicides, insect tolerance to different kind of insects, in particular tolerance to lepidopteran and coleopteran insects, herbicide tolerance with one or several types of insect resistance, herbicide tolerance with increased yield as well as a combination of herbicide tolerance and tolerance to abiotic conditions. BASF SE 240867W001

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[0596] Plants comprising singular or stacked traits as well as the genes and events providing these traits are known (http: / / www.isaaa.org / gmapprovaldatabase) and (http: / / cera- gmc.org / GMCropDatabase).

[0597] Further information on specific events and methods to detect them can be found for canola events MS1 , MS8, RF3, GT73, MON88302, KK179 in WG01 / 031042, WG01 / 041558, WG01 / 041558, WG02 / 036831 , WO11 / 153186, WO13 / 003558, for cotton events MON 1445, MON 15985, MON531 (MON 15985), LLCotton25, MON88913, COT102, 281-24-236, 3006-210- 23, COT67B, GHB614, T304-40, GHB119, MON88701 , 81910 in WO02 / 034946, W002 / 100163, W002 / 100163, W003 / 013224, WO04 / 072235, WO04 / 039986, WO05 / 103266, W005 / 103266, WO06 / 128573, W007 / 017186, W008 / 122406, W008 / 151780, WO12 / 134808, WO13 / 112527, for corn events GA21 , MON810, DLL25, TC1507, MON863, MIR604, LY038, MON88017, 3272, 59122, NK603, MIR162, MON89034, 98140, 32138, MON87460, 5307, 4114, MON87427, DAS40278, MON87411 , 33121 , MON87403, MON87419 in W098 / 044140, US02 / 102582, US03 / 126634, WO04 / 099447, W004 / 011601 , W005 / 103301 , W005 / 061720, W005 / 059103, WO06 / 098952, WO06 / 039376, US2007 / 292854, WO07 / 142840, W007 / 140256, W008 / 112019, W009 / 103049, WO09 / 111263, W010 / 077816, WO11 / 084621 , WO1 1 / 062904, WO11 / 022469, WO13 / 169923, WO14 / 116854, WO15 / 053998, WO15 / 142571 , for potato events E12, F10, J3, J55, V11 , X17, Y9 in WO14 / 178910, WO14 / 178913, WO1 4 / 178941 , WO14 / 179276, WO16 / 183445, WO17 / 062831 , WO17 / 062825, for rice events LLRICE06, LLRICE601 , LLRICE62 in WO00 / 026345, WO00 / 026356, WO00 / 026345 for soybean events H7-1 , MON89788, A2704-12, A5547-127, DP305423, DP356043, MON87701 , MON87769, CV127, MON87705, DAS68416-4, MON87708, MON87712, SYHT0H2, DAS81419, DAS81419 X DAS44406-6, MON87751 in WO04 / 074492, W006 / 130436, WO06 / 108674, WO06 / 108675, WO08 / 054747, W008 / 002872, WO09 / 064652, WO09 / 102873, W010 / 080829, W010 / 037016, WO11 / 066384, WO11 / 034704, WO12 / 051199, WO12 / 082548, WO13 / 016527, WO13 / 016516, WO14 / 201235.

[0598] The use of compositions according to the invention on cultivated plants may result in effects which are specific to a cultivated plant comprising a certain gene or event. These effects may comprise enhanced yield, enhanced resistance or tolerance to insects, nematodes, fungal, bacterial, mycoplasma, viral or viroid pathogens as well as early vigor, early or delayed ripening, cold or heat tolerance as well as changed amino acid or fatty acid spectrum or content.

[0599] It has been found that the pesticidal activity of the compounds of the invention may be enhanced by the insecticidal trait of a modified plant. Furthermore, it has been found that the compounds of the invention are suitable for preventing insects to become resistant to the insecticidal trait or for combating pests, which already have become resistant to the insecticidal trait of a modified plant. Moreover, the compounds of the invention are suitable for combating pests, against which the insecticidal trait is not effective, so that a complementary insecticidal activity can advantageously be used.

[0600] The term "plant propagation material" refers to all the generative parts of the plant e.g. seeds and vegetative plant material e.g. cuttings and tubers (e.g. potatoes), which can be used for the multiplication of the plant. This includes seeds, roots, fruits, tubers, bulbs, rhizomes, shoots, sprouts and other parts of plants. Seedlings and young plants, which are to be trans-planted after germination or after emergence from soil, may also be included. These plant propagation BASF SE 240867W001

[0601] B19464WO

[0602] 59 materials may be treated prophylactically with a plant protection compound either at or before planting or transplanting.

[0603] The term “seed” embraces seeds and plant propagules of all kinds including but not limited to true seeds, seed pieces, suckers, corms, bulbs, fruit, tubers, grains, cuttings, cut shoots and the like, and means in a preferred embodiment true seeds.

[0604] In general, "pesticidally effective amount" means the amount of active ingredient needed to achieve an observable effect on growth, including the effects of necrosis, death, retardation, prevention, and removal, destruction, or otherwise diminishing the occurrence and activity of the target organism. The pesticidally effective amount can vary for the various compounds / compositions used in the invention. A pesticidally effective amount of the compositions will also vary according to the prevailing conditions e.g. desired pesticidal effect and duration, weather, target species, locus, mode of application.

[0605] In the case of soil treatment, in furrow application or of application to the pests dwelling place or nest, the quantity of active ingredient ranges from 0.0001 to 500 g per 100 m2, preferably from 0.001 to 20 g per 100 m2.

[0606] For use in treating crop plants, e.g. by foliar application, the rate of application of the active ingredients of this invention may be in the range of 0.0001 g to 4000 g per hectare, e.g. from 1 g to 2 kg per hectare or from 1 g to 750 g per hectare, desirably from 1 g to 100 g per hectare, more desirably from 10 g to 50 g per hectare, e.g., 10 to 20 g per hectare, 20 to 30 g per hectare, 30 to 40 g per hectare, or 40 to 50 g per hectare.

[0607] The compounds of the invention are particularly suitable for use in the treatment of seeds in order to protect the seeds from insect pests, in particular from soil-living insect pests, and the resulting seedling’s roots and shoots against soil pests and foliar insects. The invention therefore also relates to a method for the protection of seeds from insects, in particular from soil insects, and of the seedling's roots and shoots from insects, in particular from soil and foliar insects, said method comprising treating the seeds before sowing and / or after pregermination with a compound of the invention. The protection of the seedling's roots and shoots is preferred. More preferred is the protection of seedling’s shoots from piercing and sucking insects, chewing insects and nematodes.

[0608] The term “seed treatment” comprises e.g. seed dressing, seed coating, seed dusting, seed soaking, seed pelleting, and in-furrow application methods. Preferably, the seed treatment application of the active compound is carried out by spraying or by dusting the seeds before sowing of the plants and before emergence of the plants.

[0609] The invention also comprises seeds coated with or containing the active compound. The term "coated with and / or containing" generally signifies that the active ingredient is for the most part on the surface of the propagation product at the time of application, although a greater or lesser part of the ingredient may penetrate into the propagation product, depending on the method of application. When the said propagation product is (re)planted, it may absorb the active ingredient.

[0610] Suitable seed is e.g. seed of cereals, root crops, oil crops, vegetables, spices, ornamentals, e.g. seed of durum and other wheat, barley, oats, rye, maize (fodder maize and sugar maize I sweet and field corn), soybeans, oil crops, crucifers, cotton, sunflowers, bananas, rice, oilseed rape, turnip rape, sugarbeet, fodder beet, eggplants, potatoes, grass, lawn, turf, fodder grass, BASF SE 240867W001

[0611] B19464WO

[0612] 60 tomatoes, leeks, pumpkin / squash, cabbage, iceberg lettuce, pepper, cucumbers, melons, Brassica species, melons, beans, peas, garlic, onions, carrots, tuberous plants e.g. potatoes, sugar cane, tobacco, grapes, petunias, geranium / pelargoniums, pansies and impatiens.

[0613] In addition, the active compound may also be used for the treatment of seeds from plants, which have been modified by mutagenisis or genetic engineering, and which e.g. tolerate the action of herbicides or fungicides or insecticides.

[0614] Conventional seed treatment formulations include e.g. flowable concentrates FS, solutions LS, suspoemulsions (SE), powders for dry treatment DS, water dispersible powders for slurry treatment WS, water-soluble powders SS and emulsion ES and EC and gel formulation GF. These formulations can be applied to the seed diluted or undiluted. Application to the seeds is carried out before sowing, either directly on the seeds or after having pregerminated the latter. Preferably, the formulations are applied such that germination is not included.

[0615] The active substance concentrations in ready-to-use formulations, which may be obtained after two-to-tenfold dilution, are preferably from 0.01 to 60% by weight, more preferably from 0.1 to 40% by weight.

[0616] In a preferred embodiment a FS formulation is used for seed treatment. Typically, a FS formulation may comprise 1-800 g / l of active ingredient, 1-200 g / l Surfactant, 0 to 200 g / l antifreezing agent, 0 to 400 g / l of binder, 0 to 200 g / l of a pigment and up to 1 liter of a solvent, preferably water.

[0617] Especially preferred FS formulations of the compounds of the invention for seed treatment usually comprise from 0.1 to 80% by weight (1 to 800 g / l) of the active ingredient, from 0.1 to 20% by weight (1 to 200 g / l) of at least one surfactant, e.g. 0.05 to 5% by weight of a wetter and from 0.5 to 15% by weight of a dispersing agent, up to 20% by weight, e.g. from 5 to 20% of an anti-freeze agent, from 0 to 15% by weight, e.g. 1 to 15% by weight of a pigment and / or a dye, from 0 to 40% by weight, e.g. 1 to 40% by weight of a binder (sticker / adhesion agent), optionally up to 5% by weight, e.g. from 0.1 to 5% by weight of a thickener, optionally from 0.1 to 2% of an anti-foam agent, and optionally a preservative e.g. a biocide, antioxidant or the like, e.g. in an amount from 0.01 to 1% by weight and a filler / vehicle up to 100% by weight.

[0618] In the treatment of seed, the application rates of the compounds of the invention are generally from 0.1 g to 10 kg per 100 kg of seed, preferably from 1 g to 5 kg per 100 kg of seed, more preferably from 1 g to 1000 g per 100 kg of seed and in particular from 1 g to 200 g per 100 kg of seed, e.g. from 1 g to 100 g or from 5 g to 100 g per 100 kg of seed.

[0619] The invention therefore also relates to seed comprising a compound of the invention, or an agriculturally useful salt thereof, as defined herein. The amount of the compound of the invention or the agriculturally useful salt thereof will in general vary from 0.1 g to 10 kg per 100 kg of seed, preferably from 1 g to 5 kg per 100 kg of seed, in particular from 1 g to 1000 g per 100 kg of seed. For specific crops e.g. lettuce the rate can be higher.

[0620] The compounds of the invention may also be used for improving the health of a plant. Therefore, the invention also relates to a method for improving plant health by treating a plant, plant propagation material and / or the locus where the plant is growing or is to grow with an effective and non-phytotoxic amount of a compound of the invention. BASF SE 240867W001

[0621] B19464WO

[0622] 61

[0623] As used herein “an effective and non-phytotoxic amount” means that the compound is used in a quantity which allows to obtain the desired effect but which does not give rise to any phytotoxic symptom on the treated plant or on the plant grown from the treated propagule or treated soil. "Plant health" is defined as a condition of the plant and / or its products which is determined by several aspects alone or in combination with each other e.g. yield (e.g. increased biomass and / or increased content of valuable ingredients), quality (e.g. improved content or composition of certain ingredients or shelf life), plant vigour (e.g. improved plant growth and / or greener leaves (“greening effect”), tolerance to abiotic (e.g. drought) and / or biotic stress (e.g. disease) and production efficiency (e.g., harvesting efficiency, processability).

[0624] The above identified indicators for the health condition of a plant may be interdependent and may result from each other. Each indicator is defined in the art and can be determined by methods known to a skilled person.

[0625] The compounds of the invention are also suitable for use against non-crop insect pests. For use against said non-crop pests, compounds of the invention can be used as bait composition, gel, general insect spray, aerosol, as ultra-low volume application and bed net (impregnated or surface applied). Furthermore, drenching and rodding methods can be used.

[0626] As used herein, the term “non-crop insect pest” refers to pests, which are particularly relevant for non-crop targets, e.g. ants, termites, wasps, flies, ticks, mosquitoes, bed bugs, crickets, or cockroaches.

[0627] The bait can be a liquid, a solid or a semisolid preparation (e.g. a gel). The bait employed in the composition is a product, which is sufficiently attractive to incite insects e.g. ants, termites, wasps, flies, mosquitoes, crickets etc. or cockroaches to eat it. The attractiveness can be manipulated by using feeding stimulants or sex pheromones. Food stimulants are preferably chosen from animal and / or plant proteins (meat-, fish- or blood meal, insect parts, egg yolk), from fats and oils of animal and / or plant origin, or mono-, oligo- or polyorganosaccharides, especially from sucrose, lactose, fructose, dextrose, glucose, starch, pectin or even molasses or honey. Fresh or decaying parts of fruits, crops, plants, animals, insects or specific parts thereof can also serve as a feeding stimulant. Sex pheromones are known to be more insect specific. Specific pheromones are known (http: / / www.pherobase.com).

[0628] For use in bait compositions, the typical content of active ingredient is from 0.001 wt% to 15 wt%, desirably from 0.001 wt% to 5 wt% of active compound.

[0629] Formulations of the compounds of the invention as aerosols (e.g. in spray cans), oil sprays or pump sprays are highly suitable for professional or non-professional users for controlling pests e.g. flies, fleas, ticks, bed bugs, mosquitoes or cockroaches. Aerosol recipes are preferably composed of the active compound, solvents, furthermore auxiliaries e.g. emulsifiers, perfume oils, if appropriate stabilizers, and, if required, propellants.

[0630] The oil spray formulations differ from the aerosol recipes in that no propellants are used. For use in spray compositions, the content of active ingredient is from 0.001 to 80 wt%, preferably from 0.01 to 50 wt% and most preferably from 0.01 to 15 wt%.

[0631] The compounds of the invention and its respective compositions can also be used in mosquito and fumigating coils, smoke cartridges, vaporizer plates or long-term vaporizers and also in moth papers, moth pads or other heat-independent vaporizer systems. BASF SE 240867W001

[0632] B19464WO

[0633] 62

[0634] Methods to control infectious diseases transmitted by insects (e.g. malaria, dengue and yellow fever, lymphatic filariasis, and leishmaniasis) with compounds of the invention and its respective compositions also comprise treating surfaces of huts and houses, air spraying and impregnation of curtains, tents, clothing items, bed nets, tsetse-fly trap. Insecticidal compositions for application to fibers, fabric, knitgoods, nonwovens, netting material or foils and tarpaulins preferably comprise a mixture including the insecticide, optionally a repellent and at least one binder.

[0635] The compounds of the invention and its compositions can be used for protecting wooden materials e.g. trees, board fences, sleepers, frames, artistic artifacts, etc. and buildings, but also construction materials, furniture, leathers, fibers, vinyl articles, electric wires and cables etc. from ants, termites and / or wood or textile destroying beetles, and for controlling ants and termites from doing harm to crops or human beings (e.g. when the pests invade into houses and public facilities or nest in yards, orchards or parks).

[0636] Customary application rates in the protection of materials are, e.g., from 0.001 g to 2000 g or from 0.01 g to 1000 g of active compound per m2treated material, desirably from 0.1 g to 50 g per m2.

[0637] Insecticidal compositions for use in the impregnation of materials typically contain from 0.001 to 95 wt%, preferably from 0.1 to 45 wt%, and more preferably from 1 to 25 wt% of at least one repellent and / or insecticide.

[0638] Digital application

[0639] The compounds of the invention and the compositions containing them may be applied in combination with, or by utilizing smart agricultural technologies, such as precision agriculture, remote and proximate imaging and image recognition, or smart agricultural site management programs. These smart agricultural technologies typically include models, e.g. computer programs, that support the user by considering information from a wide variety of sources to increase the quality and yield of harvested material, reduce damage by pests including the prediction of pest pressure and smart application of crop protection products, secure environmental protection, support quick and reliable agronomic decision making, reduce usage of fertilizers and crop protection products, reduce product residues in consumables increase spatial and temporal precision of agronomical measures, automate processes, and enable traceability of measures.

[0640] Commercially available systems which include agronomic models are e.g. FieldScripts™ from The Climate Corporation, Xarvio™ from BASF, AGLogic™ from John Deere, etc.

[0641] Information input for these models include but is not limited to soil data, information on the plants that are currently growing or that may grow at the area of interest including crop plants and / or unwanted vegetation, weather information, information on the location of the area and directly derivable information thereof, information on pest pressure, information on beneficial organisms, and I or historic information of any of the aforementioned.

[0642] The information usable for precision agriculture may be based on input by at least one user, be accessible from external data sources and databases, or be based on sensor data. Data sources typically includes proximate-detection systems like soil-borne sensors and remote sensing as may be achieved by imaging with unmanned airborne vehicles like drones, or satellites. Sensors may be included in an Internet-of-Things system and may be directly or BASF SE 240867W001

[0643] B19464WO

[0644] 63 indirectly connected to the processing unit, e.g. via a wireless network and / or cloud applications. The information is typically taken into account by at least one processing unit and used to provide recommendations and generate control signals.

[0645] Typical technologies that are used in smart agricultural technologies include self-steering robots (such as tractors, harvesters, drones), artificial intelligence (e.g. machine learning), imaging technologies (e.g. image segmentation technologies), big data analysis, and model generation, cloud computing, and machine-to-machine communication.

[0646] Precision agriculture such as precision farming is characterized by spatially and / or temporally resolved, targeted application of active ingredients like pesticides, plant-growth-regulators, fertilizers, and / or water including the variation of application rates over the agronomic site, zone or spot application, and of the spatially and / or temporally resolved, targeted planting or seeding of desired plant propagation material to a agronomic site. Precision farming typically includes the use of geo-positioning technologies like GPS for gaining information on the location and boundaries of the area of interest, the utilized application equipment, sensing equipment and recorded data, and to control the actions of farm vehicles such as spraying. By combining geopositioning data with (digital) maps, it is possible to (semi)-automate agricultural measures at the site of interest, e.g. by using (semi)-autonomous spraying or seeding equipment.

[0647] Precision farming may typically include the application of smart spraying equipment, e.g. spot spraying, and precision spraying at a farm, e.g. by irrigation systems, tractors, robots, helicopters, airplanes, unmanned aerial vehicles, such as drones. Such equipment usually includes input sensors (such as e.g. a camera) and a processing unit configured to analyze the input data and configured to provide a recommendation or decision based on the analysis of the input data to apply the compounds of the invention or compositions comprising them to the agronomic site, e.g. the soil, the crop plants, or to control pests in a specific and precise manner. For example, pests may be detected, identified, and / or classified from imagery acquired by a camera. Such identification and / classification can make use of image processing algorithms, which may utilize artificial intelligence (e.g. machine learning algorithms), or decision trees. In this manner, the compounds or compositions described herein can be applied only at the required location, point in time and dose rate.

[0648] Pests

[0649] The compounds of the invention are especially suitable for efficiently combating animal pests e.g. arthropods, gastropods and nematodes including: insects from the order of Lepidoptera, e.g. Achroia grisella, Acleris spp. e.g. A. fimbriana, A. gloverana, A. variana; Acrolepiopsis assectella, Acronicta major, Adoxophyes spp. e.g. A. cyrtosema, A. orana; Aedia leucomelas, Agrotis spp. e.g. A. exclamationis, A. fucosa, A. ipsilon, A. orthogoma, A. segetum, A. subterranea; Alabama argillacea, Aleurodicus dispersus, Alsophila pometaria, Ampelophaga rubiginosa, Amyelois transitella, Anacampsis sarcitel la, Anagasta kuehniella, Anarsia lineatella, Anisota sanatoria, Antheraea pernyi, Anticarsia (=Thermesia) spp. e.g. A. gemmatalis; Apamea spp., Aproaerema modicella, Archips spp. e.g. A. argyrospila, A. fuscocupreanus, A. rosana, A. xyloseanus; Argyresthia conjugella, Argyroploce spp., Argyrotaenia spp. e.g. A. velutinana; Athetis mindara, Austroasca viridigrisea, Autographa gamma, Autographa nigrisigna, Barathra brassicae, Bedellia spp., Bonagota salubricola, Borbo cinnara, Bucculatrix thurberiella, Bupalus piniarius, Busseola spp., Cacoecia BASF SE 240867W001

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[0651] 64 spp. e.g. C. murinana, C. podana; Cactoblastis cactorum, Cadra cautella, Calingo braziliensis, Caloptilis theivora, Capua reticulana, Carposina spp. e.g. C. niponensis, C. sasakii; Cephus spp., Chaetocnema aridula, Cheimatobia brumata, Chilo spp. e.g. C. Indicus, C. suppressalis,

[0652] C. partellus; Choreutis pariana, Choristoneura spp. e.g. C. conflictana, C. fumiferana, C. longicellana, C. murinana, C. occidentalis, C. rosaceana; Chrysodeixis (=Pseudoplusia) spp., e.g. C. eriosoma, C. includens; Cirphis unipuncta, Clysia ambiguella, Cnaphalocerus spp., Cnaphalocrocis medinalis, Cnephasia spp., Cochylis hospes, Coleophora spp., Colias eurytheme, Conopomorpha spp., Conotrachelus spp., Copitarsia spp., Corcyra cephalonica, Crambus caliginosellus, Crambus teterrellus, Crocidosema (=Epinotia) aporema, Cydalima (=Diaphania) perspectalis, Cydia (=Carpocapsa) spp., e.g. C. pomonella, C. latiferreana; Dalaca noctuides, Datana integerrima, Dasychira pinicola, Dendrolimus spp., e.g. D. pini, D. spectabilis,

[0653] D. sibiricus; Desmia funeralis, Diaphania spp., e.g. D. nitidalis, D. hyalinata; Diatraea grandiosella, Diatraea saccharalis, Diphthera festiva, Earias spp. e.g. E. insulana, E. vittella; Ecdytolopha aurantianu, Egira (=Xylomyges) curialis, Elasmopalpus lignosellus, Eldana saccharina, Endopiza viteana, Enno-mos subsignaria, Eoreuma loftini, Ephestia spp., e.g. E. cautella, E. elutella, E. kuehniella; Epinotia aporema, Epiphyas postvittana, Erannis tiliaria, Erionota thrax, Etiella spp., Eulia spp., Eupoecilia ambiguella, Euproctis chrysorrhoea, Euxoa spp., Evetria bouliana, Faronta albilinea, Feltia spp. e.g. F. subterranean; Galleria mellonella, Gracillaria spp., Grapholita spp. e.g. G. funebrana, G. molesta, G. inopinata; Halysidota spp., Harrisina americana, Hedylepta spp., Helicoverpa spp. e.g. H. armigera (=Heliothis armigera), H. zea (=Heliothis zea); Heliothis spp. e.g. H. assulta, H. subflexa, H. virescens; Hellula spp. e.g. H. undalis, H. rogatalis; Helocoverpa gelotopoeon, Hemileuca oliviae, Herpetogramma licarsisalis, Hibernia defoliaria, Hofmannophila pseudospretella, Homoeosoma electellum, Homona magnanima, Hypena scabra, Hyphantria cunea, Hyponomeuta padella, Hyponomeuta malinellus, Kakivoria flavofasciata, Keiferia lycopersicella, Lambdina fiscellaria fiscel laria, Lambdina fiscellaria lugubrosa, Lamprosema indicata, Laspeyresia molesta, Leguminivora glycinivorella, Lerodea eufala, Leucinodes orbonalis, Leucoma salicis, Leucoptera spp. e.g. L. coffeella, L. scitella; Leuminivora lycinivorella, Lithocolletis blancardella, Lithophane antennata, Llattia octo (=Amyna axis), Lobesia botrana, Lophocampa spp., Loxagrotis albicosta, Loxostege spp. e.g. L. sticticalis, L. cereralis; Lymantria spp., e.g. L. dispar, L. monacha; Lyonetia clerkella, Lyonetia prunifoliella, Malacosoma spp., e.g. M. americanum, M. californicum, M. constrictum, M. neu-stria; Mamestra spp., e.g. M. brassicae, M. configurata; Mamstra brassicae, Manduca spp. e.g. M. quinquemaculata, M. sexta; Marasmia spp, Marmara spp., Maruca testulalis, Megalopyge lanata, Melanchra picta, Melanitis leda, Mods spp., e.g. M. lapites, M. repanda; Mods latipes, Monochroa fragariae, Mythimna separata, Nemapogon cloacella, Neoleucinodes elegantalis, Nepytia spp., Nymphula spp., Oiketicus spp., Omiodes indicata, Omphisa anastomosalis, Operophtera brumata, Orgyia pseudotsugata, Oria spp., Orthaga thyrisalis, Ostrinia spp. e.g. O. nubilalis; Oulema oryzae, Paleacrita vernata, Panolis flammea, Parnara spp., Papaipema nebris, Papilio cresphontes, Paramyelois transitella, Paranthrene regalis, Paysandisia archon, Pectinophora spp. e.g. P. gossypiella; Peridroma saucia, Perileucoptera spp., e.g. P. coffeella; Phalera bucephala, Phryganidia californica, Phthorimaea spp. e.g. P. operculella; Phyllocnistis citrella, Phyllonorycter spp. e.g. P. blancardella, P. crataegella, P. issikii, P. ringoniella; Pieris spp. e.g. P. brassicae, P. rapae, P. napi; Pilocrocis tripunctata, Plathypena scabra, Platynota spp. e.g. P. flavedana, P. idaeusalis, P. stultana; Platyptilia BASF SE 240867W001

[0654] B19464WO

[0655] 65 carduidactyla, Plebejus argus, Plo-dia interpunctella, Plusia spp, Plutella maculipennis, Plutella xylostella, Pontia protodica, Prays spp., Prodenia spp., Proxenus lepigone, Pseudaletia spp. e.g. P. sequax, P. unipuncta; Pyrausta nubilalis, Rachiplusia nu, Richia albicosta, Rhizobius ventralis, Rhyacionia frustrana, Sabulodes aegrotata, Schizura concinna, Schoenobius spp., Schreckensteinia festaliella, Scirpophaga spp. e.g. S. incertulas, S. innotata; Scotia segetum, Sesamia spp. e.g. S. inferens, Seudyra subflava, Sitotroga cerealella, Sparganothis pilleriana, Spilonota lechriaspis, S. ocelli-na, Spodoptera (=Lamphygma) spp. e.g. S. cosmoides, S. eridania, S. exigua, S. frugiperda, S. latisfascia, S. littoralis, S. litura, S. omithogalli; Stigmella spp., Stomopteryx subsecivella, Strymon bazochii, Sylepta derogata, Synanthedon spp. e.g. S. exitiosa, Tecia solanivora, Telehin licus, Thaumatopoea pityocampa, Thaumatotibia (=Cryptophlebia) leucotreta, Thaumetopoea pityocampa, Thecla spp., Theresimima ampelophaga, Thyrinteina spp, Tildenia inconspicuella, Tinea spp. e.g. T. cloacella, T. pellionella; Tineola bisselliella, Tortrix spp. e.g. T. viridana; Trichophaga tapetzella, Trichoplusia spp. e.g. T. ni; Tuta (=Scrobipalpula) absoluta, lldea spp. e.g. II. rubigalis, II. rubigalis; Virachola spp., Yponomeuta padella, and Zeiraphera canadensis; insects from the order of Coleoptera, e.g. Acalymma vittatum, Acanthoscehdes obtectus, Adoretus spp., Agelastica alni, Agrilus spp. e.g. A. anxius, A. planipennis, A. sinuatus; Agriotes spp. e.g. A. fuscicollis, A. lineatus, A. obscurus; Alphitobius diaperinus, Amphimallus solstitialis, Anisandrus dispar, Anisoplia austriaca, Anobium punctatum, Anomala corpulenta, Anomala rufocuprea, Anoplophora spp. e.g. A. glabripennis; Anthonomus spp. e.g. A. eugenii, A. grandis, A. pomorum; Anthrenus spp., Aphthona euphoridae, Apion spp., Apogonia spp., Athous haemorrhoidalis, Atomaria spp. e.g. A. linearis; Attagenus spp., Aulacophora femoralis, Blastophagus piniperda, Blitophaga undata, Bruchidius obtectus, Bruchus spp. e.g. B. lentis, B. pisorum, B. rufimanus; Byctiscus betulae, Callidiellum rufipenne, Callopistria floridensis, Callosobruchus chinensis, Cameraria ohridella, Cassida nebulosa, Cerotoma trifurcata, Cetonia aurata, Ceuthorhynchus spp. e.g. C. assimilis, C. napi; Chaetocnema tibialis, Cleonus mendicus, Conoderus spp. e.g. C. vespertinus; Conotrachelus nenuphar, Cosmopolites spp., Costelytra zealandica, Crioceris asparagi, Cryptolestes ferrugineus, Cryptorhynchus lapathi, Ctenicera spp. e.g. C. destructor; Curculio spp., Cylindrocopturus spp., Cyclocephala spp., Dac- tylispa balyi, Dectes texanus, Dermestes spp., Diabrotica spp. e.g. D. undecimpunctata, D. speciosa, D. longicornis, D. semipunctata, D. virgifera; Diaprepes abbreviates, Dichocrocis spp., Dicladispa armigera, Diloboderus abderus, Diocalandra frumenti (Diocalandra stigmaticollis) , Enaphalodes rufulus, Epilachna spp. e.g. E. varivestis, E. vigintioctomaculata; Epitrix spp. e.g. E. hirtipennis, E. similaris; Eutheola humilis, Eutinobothrus brasiliensis, Faustinus cubae, Gibbium psylloides, Gnathocerus cornutus, Hellula undalis, Heteronychus arator, Hylamorpha elegans, Hylobius abietis, Hylotrupes bajulus, Hypera spp., e.g. H. brunneipennis, H. postica; Hypomeces squamosus, Hypothenemus spp., Ips typographus, Lachnosterna consanguinea, Lasioderma serricorne, Latheticus oryzae, Lathridius spp., Lerna spp. e.g. L. bilineata, L. melanopus; Leptinotarsa spp. e.g. L. decemlineata; Leptispa pygmaea, Limonius californi-cus, Lissorhoptrus oryzophilus, Lixus spp., Luperodes spp., Lyctus spp. e.g. L. bruneus; Liogenys fuscus, Macrodactylus spp. e.g. M. subspinosus; Maladera matrida, Megaplatypus mutates, Megascelis spp., Melanotus communis, Meligethes spp. e.g. M. aeneus; Melolontha spp. e.g. M. hippocastani, M. melolontha; Metamasius hemipterus, Microtheca spp., Migdolus spp. e.g. M. fryanus, Monochamus spp. e.g. M. alternatus; Naupactus xanthographus, Niptus hololeucus, BASF SE 240867W001

[0656] B19464WO

[0657] 66

[0658] Oberia brevis, Oemona hirta, Oryctes rhinoceros, Oryzaephilus surinamensis, Oryzaphagus oryzae, Otiorrhynchus sulcatus, Otiorrhynchus ovatus, Otiorrhynchus sulcatus, Oulema melanopus, Oulema oryzae, Oxycetonia jucunda, Phaedon spp. e.g. P. brassicae, P. cochleariae; Phoracantha recurva, Phyllobius pyri, Phyllopertha horticola, Phyllophaga spp. e.g. P. helleri; Phyllotreta spp. e.g. P. chrysocephala, P. nemorum, P. striolata, P. vittula; Phyllopertha horticola, Popillia japonica, Premnotrypes spp., Psacothea hilaris, Psylliodes chrysocephala, Prostephanus truncates, Psylliodes spp., Ptinus spp., Pulga saltona, Rhizopertha dominica, Rhynchophorus spp. e.g. R. billineatus, R. ferrugineus, R. palmarum, R. phoenicis, R. vulneratus; Saperda Candida, Scolytus schevyrewi, Scyphophorus acupunctatus, Sitona lineatus, Sitophilus spp. e.g. S. granaria, S. oryzae, S. zeamais; Sphenophorus spp. e.g. S. levis; Stegobium paniceum, Sternechus spp. e.g. S. subsignatus; Strophomorphus ctenotus, Symphyletes spp., Tanymecus spp., Tenebrio molitor, Tenebrioides mauretanicus, Tribolium spp. e.g. T. castaneum; Trogoderma spp., Tychius spp., Xylotrechus spp. e.g. X. pyrrhoderus; and, Zabrus spp. e.g. Z. tenebrioides; insects from the order of Diptera e.g. Aedes spp. e.g. A. aegypti, A. albopictus, A. vexans; Anastrepha ludens, Anopheles spp. e.g. A. albimanus, A. crucians, A. freeborni, A. gambiae, A. leucosphyrus, A. maculipennis, A. minimus, A. quadrimaculatus, A. sinensis; Bactrocera invadens, Bibio hortulanus, Calliphora erythrocephala, Calliphora vicina, Ceratitis capitata, Chrysomyia spp. e.g. C. bezziana, C. hominivorax, C. macellaria; Chrysops atlanticus, Chrysops discalis, Chrysops silacea, Cochliomyia spp. e.g. C. hominivorax; Contarinia spp. e.g. C. sorghicola; Cordylobia anthropophaga, Culex spp. e.g. C. nigripalpus, C. pipiens, C. quinquefasciatus, C. tarsalis, C. tritaeniorhynchus; Culicoides furens, Culiseta inornata, Culiseta melanura, Cuterebra spp., Dacus cucurbitae, Dacus oleae, Dasineura brassicae, Dasineura oxycoccana, Delia spp. e.g. D. antique, D. coarctata, D. platura, D. radicum; Dermatobia hominis, Drosophila spp. e.g. D. suzukii, Fannia spp. e.g. F. canicularis; Gastraphilus spp. e.g.

[0659] G. intestinalis; Geomyza tipunctata, Glossina spp. e.g. G. fuscipes, G. morsitans, G. palpalis, G. tachinoides; Haematobia irritans, Haplodiplosis equestris, Hippelates spp., Hylemyia spp. e.g.

[0660] H. platura; Hypoderma spp. e.g. H. lineata; Hyppobosca spp., Hydrellia philippina, Leptoconops torrens, Liriomyza spp. e.g. L. sativae, L. trifolii; Lucilia spp. e.g. L. caprina, L. cuprina, L. sericata; Lycoria pectoralis, Mansonia titillanus, Mayetiola spp. e.g. M. destructor; Musca spp. e.g. M. autumnalis, M. domestica; Muscina stabulans, Oestrus spp. e.g. O. ovis; Opomyza florum, Oscinella spp. e.g. O. frit; Orseolia oryzae, Pegomya hysocyami, Phlebotomus argentipes, Phorbia spp. e.g. P. antiqua, P. brassicae, P. coarctata; Phytomyza gymnostoma, Prosimulium mixtum, Psila rosae, Psorophora columbiae, Psorophora discolor, Rhagoletis spp. e.g. R. cerasi, R. cingulate, R. indifferens, R. mendax, R. pomonella; Rivellia quadrifasciata, Sarcophaga spp. e.g. S. haemorrhoidalis; Simulium vittatum, Sitodiplosis mosellana, Stomoxys spp. e.g. S. calcitrans; Tabanus spp. e.g. T. atratus, T. bovinus, T. lineola, T. similis; Tannia spp., Thecodiplo-sis japonensis, Tipula oleracea, Tipula paludosa, Wohlfahrtia spp, and Zaprionus indianus; insects from the order of Thysanoptera e.g., Baliothrips biformis, Dichromothrips corbetti, Dichromothrips ssp., Echinothrips americanus, Enneothrips flavens, Frankliniella spp. e.g. F. fusca, F. occidentalis, F. tritici; Heliothrips spp., Hercinothrips femoralis, Kakothrips spp., Microcephalothrips abdominalis, Neohydatothrips samayunkur, Pezothrips kellyanus, Rhipiphorothrips cruentatus, Scirtothrips spp. e.g. S. citri, S. dorsalis, S. perseae; BASF SE 240867W001

[0661] B19464WO

[0662] 67

[0663] Stenchaetothrips spp, Taeniothrips cardamoni, Taeniothrips inconsequens, Thrips spp. e.g. T. imagines, T. hawaiiensis, T. oryzae, T. palmi, T. parvispinus, T. tabaci; insects from the order of Hemiptera e.g., Acizzia jamatonica, Acrosternum spp., e.g. A. hilare; Acyrthosipon spp., e.g. A. onobrychis, A. pisum; Adelges laricis, Adelges tsugae, Adelphocoris spp., e.g. A. rapidus, A. superbus; Aeneolamia spp., Agonoscena spp., Aulacorthum solani, Aleurocanthus woglumi, Aleurodes spp., Aleurodicus disperses, Aleurolobus barodensis, Aleurothrixus spp., Amrasca spp., Anasa tristis, Antestiopsis spp., Anuraphis cardui, Aonidiella spp., Aphanostigma piri, Aphidula nasturtii, Aphis spp. e.g. A. craccivora, A. fabae, A. forbesi, A. gossypii, A. grossulariae, A. maidiradicis, A. pomi, A. sambuci, A. schneideri, A. spiraecola; Arboridia apicalis, Arilus critatus, Aspidiella spp., Aspidiotus spp., Atanus spp., Aulacaspis yasumatsui, Aulacorthum solani, Bactericera cockerelli (Paratrioza cockerelli), Bemisia spp. e.g. B. argentifolii, B. tabaci (Aleurodes tabaci); Blissus spp. e.g. B. leucopterus; Brachycaudus spp. e.g. B. cardui, B. helichrysi, B. persicae, B. prunicola; Brachycolus spp., Brachycorynella as- paragi, Brevicoryne brassicae, Cacopsylla spp. e.g. C. fulguralis, C. pyricola (Psylla piri);

[0664] Calligypona marginata, Calocoris spp., Campylomma livida, Capitophorus horni, Carneocephala fulgida, Cavelerius spp., Ceraplastes spp., Ceratovacuna lanigera, Ceroplastes ceriferus, Cerosipha gossypii, Chaetosiphon fragaefolii, Chionaspis tegalensis, Chlorita onukii, Chromaphis juglandicola, Chrysomphalus ficus, Cicadulina mbila, Cimex spp. e.g. C. hemipterus, C. lectularius; Circulifer tenellus, Coccomytilus halli, Coccus spp. e.g. C. hesperidum, C. pseudomagnoliarum; Corythucha arcuata, Creontiades dilutus, Cryptomyzus ribis, Chrysomphalus aonidum, Cryptomyzus ribis, Ctenarytaina spatulata, Cyrtopeltis notatus, Dalbulus spp., Dasynus piperis, Dialeurodes spp. e.g. D. citrifolii; Dalbulus maidis, Diaphorina spp. e.g. D. citri; Diaspis spp. e.g. D. bromeliae; Dichelops furcatus, Diconocoris hewetti, Doralis spp., Dreyfusia nordmannianae, Dreyfusia piceae, Drosicha spp., Dysaphis spp. e.g. D. plantaginea, D. pyri, D. radicola; Dysaulacorthum pseudosolani, Dysdercus spp. e.g. D. cingulatus, D. intermedius; Dysmicoccus spp., Edessa spp., Geocoris spp., Empoasca spp. e.g. E. fabae, E. solana; Epidiaspis leperii, Eriosoma spp. e.g. E. lanigerum, E. pyricola;

[0665] Erythroneura spp., Eurygaster spp. e.g. E. integriceps; Euscelis bilobatus, Euschistus spp. e.g. E. heros, E. impictiventris, E. servus; Fiorinia theae, Geococcus coffeae, Glycaspis brimblecombei, Halyomorpha spp. e.g. H. halys; Heliopeltis spp., Homalodisca vitripennis (=H. coagulata), Horcias nobilellus, Hyalopterus pruni, Hyperomyzus lactucae, Icerya spp. e.g. I. purchase; Idiocerus spp., Idioscopus spp., Laodelphax striatellus, Lecanium spp., Lecanoideus floccissimus, Lepidosaphes spp. e.g. L. ulmi; Leptocorisa spp., Leptoglossus phyllopus, Lipaphis erysimi, Lygus spp. e.g. L. hesperus, L. lineolaris, L. praten-sis; Maconellicoccus hirsutus, Marchalina hellenica, Macropes excavatus, Macrosiphum spp. e.g. M. rosae, M. avenae, M. euphorbiae; Macrosteles quadrilineatus, Mahanarva fimbriolata, Megacopta cribraria, Megoura viciae, Melanaphis pyrarius, Melanaphis sacchari, Melanocallis (=Tinocallis) caryaefoliae, Metcafiella spp., Metopolophium dirhodum, Monellia costalis, Mo-nelliopsis pecanis, Myzocallis coryli, Murgantia spp., Myzus spp. e.g. M. ascalonicus, M. cerasi, M. nicotianae, M. persicae, M. varians; Nasonovia ribisnigri, Neotoxoptera formosana, Neomegalotomus spp, Nephotettix spp. e.g. N. malayanus, N. nigropictus, N. parvus, N. vires- cens; Nezara spp. e.g. N. viridula; Nilaparvata lugens, Nysius huttoni, Oebalus spp. e.g. O. pugnax; Oncometopia spp., Orthezia praelonga, Oxycaraenus hyalinipennis, Parabemisia myricae, Parlatoria spp., Parthenolecanium spp. e.g. P. corni, P. persicae; Pemphigus spp. e.g. BASF SE 240867W001

[0666] B19464WO

[0667] 68

[0668] P. bursarius, P. populivenae; Peregrinus maidis, Perkinsiella saccharicida, Phenacoccus spp. e.g. P. aceris, P. gossypii; Phloeomyzus passerinii, Phorodon humuli, Phylloxera spp. e.g. P. devastatrix, Piesma quadrata, Piezodorus spp. e.g. P. guildinii; Pinnaspis aspidistrae, Pianococcus spp. e.g. P. citri, P. ficus; Prosapia bicincta, Protopulvinaria pyriformis, Psallus seriatus, Pseudacysta persea, Pseudaulacaspis pentagona, Pseudococcus spp. e.g. P. comstocki; Psylla spp. e.g. P. mali; Pteromalus spp., Pulvinaria amygdali, Pyrilla spp., Quadraspidiotus spp., e.g. Q. perniciosus; Quesada gigas, Rastrococcus spp., Reduvius senilis, Rhizoecus americanus, Rhodnius spp., Rhopalomyzus ascalonicus, Rhopalosiphum spp. e.g. R. pseudobrassicas, R. insertum, R. maidis, R. padi; Sagatodes spp., Sahlbergella singularis, Saissetia spp., Sappaphis mala, Sappaphis mali, Scaptocoris spp., Scaphoideus titanus, Schizaphis graminum, Schizoneura lanuginosa, Scotinophora spp., Selenaspidus articulatus, Sitobion avenae, Sogata spp., Sogatella furcifera, Solubea insularis, Spissistilus festinus (=Stictocephala festina), Stephanitis nashi, Stephanitis pyrioides, Stephanitis takeyai, Tenalaphara malayensis, Tetraleurodes perseae, Therioaphis maculate, Thyanta spp. e.g. T. accerra, T. perditor; Tibraca spp., Tomaspis spp., Toxoptera spp. e.g. T. aurantii; Trialeurodes spp. e.g. T. abutilonea, T. ricini, T. vaporariorum; Triatoma spp., Trioza spp., Typhlocyba spp., Unaspis spp. e.g. II. citri, II. yanonensis; and Viteus vitifolii,

[0669] Insects from the order Hymenoptera e.g. Acanthomyops interjectus, Athalia rosae, Atta spp. e.g. A. capiguara, A. cephalotes, A. cephalotes, A. laevigata, A. robusta, A. sexdens, A. texana, Bombus spp., Brachymyrmex spp., Camponotus spp. e.g. C. floridanus, C. pennsylvanicus, C. modoc; Cardiocondyla nuda, Chalibion sp, Crematogaster spp., Dasymutilla occidentalis, Diprion spp., Dolichovespula maculata, Dorymyrmex spp., Dryocosmus kuriphilus, Formica spp., Hoplocampa spp. e.g. H. minuta, H. testudinea; Iridomyrmex humilis, Lasius spp. e.g. L. niger, Linepithema humile, Liometopum spp., Leptocybe invasa, Monomorium spp. e.g. M. pharaonis, Monomorium, Nylandria fulva, Pachycondyla chinensis, Paratrechina longicornis, Paravespula spp., e.g. P. germanica, P. pennsylvanica, P. vulgaris; Pheidole spp. e.g. P. megacephala; Pogonomyrmex spp. e.g. P. barbatus, P. californicus, Polistes rubiginosa, Prenolepis impairs, Pseudomyrmex gracilis, Schelipron spp., Sirex cyaneus, Solenopsis spp. e.g. S. geminata, S.invicta, S. molesta, S. richteri, S. xyloni, Sphecius speciosus, Sphex spp., Tapinoma spp. e.g. T. melanocephalum, T. sessile; Tetramorium spp., e.g. T. caespitum, T. bicarinatum, Vespa spp., e.g. V. crabro; Vespula spp., e.g. V. squamosal; Wasmannia auropunctata, Xylocopa sp;

[0670] Insects from the order Orthoptera e.g. Acheta domesticus, Calliptamus italicus, Chortoicetes terminifera, Ceuthophilus spp., Diastrammena asynamora, Dociostaurus maroccanus, Gryllotalpa spp. e.g. G. africana, G. gryllotalpa; Gryllus spp., Hieroglyphus daganensis, Kraussaria angulifera, Locusta spp. e.g. L. migratoria, L. pardalina; Melanoplus spp. e.g. M. bivittatus, M. femurrubrum, M. mexicanus, M. sanguinipes, M. spretus; Nomadacris septemfasciata, Oedaleus senegalensis, Scapteriscus spp., Schistocerca spp. e.g. S. americana, S. gregaria, Stemopelmatus spp., Tachycines asynamorus, and Zonozerus variegatus;

[0671] Pests from the Class Arachnida e.g. Acari.e.g. of the families Argasidae, Ixodidae and Sar- coptidae, e.g. Amblyomma spp. (e.g. A. americanum, A. variegatum, A. maculatum), Argas spp. e.g. A. persicu), Boophilus spp. e.g. B. annulatus, B. decoloratus, B. microplus, Dermacentor spp. e.g. D.silvarum, D. andersoni, D. variabilis, Hyalomma spp. e.g. H. truncatum, Ixodes spp. BASF SE 240867W001

[0672] B19464WO

[0673] 69 e.g. I. ricinus, I. rubicundus, I. scapularis, I. holocyclus, I. pacificus, Rhipicephalus sanguineus, Ornithodorus spp. e.g. O. moubata, O. hermsi, O. turicata, Ornithonyssus bacoti, Otobius megnini, Dermanyssus gallinae, Psoroptes spp. e.g. P. ovis, Rhipicephalus spp. e.g. R. sanguineus, R. appendiculatus, Rhipicephalus evertsi, Rhizoglyphus spp., Sarcoptes spp. e.g. S. Scabiei; and Family Eriophyidae including Aceria spp. e.g. A. sheldoni, A. anthocoptes, Acallitus spp., Aculops spp. e.g. A. lycopersici, A. pelekassi; Aculus spp. e.g. A. schlechtendali; Colomerus vitis, Epitrimerus pyri, Phyllocoptruta oleivora; Eriophytes ribis and Eriophyes spp. e.g. Eriophyes sheldoni; Family Tarsonemidae including Hemitarsonemus spp., Phytonemus pallidus and Polyphagotarsonemus latus, Stenotarsonemus spp. Steneotarsonemus spinki; Family Tenuipalpidae including Brevipalpus spp. e.g. B. phoenicis; Family Tetranychidae including Eotetranychus spp., Eutetranychus spp., Oligonychus spp., Petrobia latens, Tetranychus spp. e.g. T. cinnabarinus, T. evansi, T. kanzawai, T, pacificus, T. phaseulus, T. telarius and T. urticae; Bryobia praetiosa; Panonychus spp. e.g. P. ulmi, P. citri;

[0674] Metatetranychus spp. and Oligonychus spp. e.g. O. pratensis, O. perseae, Vasates lycopersici; Raoiella indica, Family Carpoglyphidae including Carpoglyphus spp.; Penthaleidae spp. e.g. Halotydeus destructor; Family Demodicidae with species e.g. Demodex spp.; Family Trombicidea including Trombicula spp.; Family Macronyssidae including Ornothonyssus spp.; Family Pyemotidae including Pyemotes tritici; Tyrophagus putrescentiae; Family Acaridae includ-ing Acarus siro; Family Araneida including Latrodectus mactans, Eratigena agrestis, Cheiracanthium sp, Lycosa sp Achaearanea tepidariorum and Loxosceles reclusa;

[0675] Pests from the Phylum Nematoda, e.g. plant parasitic nematodes e.g. root-knot nematodes, Meloidogyne spp. e.g. M. hapla, M. incognita, M. javanica; cyst-forming nematodes, Globodera spp. e.g. G. rostochiensis; Heterodera spp. e.g. H. avenae, H. glycines, H. schachtii, H. trifolii; Seed gall nematodes, Anguina spp.; Stem and foliar nematodes, Aphelenchoides spp. e.g. A. besseyi; Sting nematodes, Belonolaimus spp. e.g. B. longicaudatus; Pine nematodes, Bursaphelenchus spp. e.g. B. lignicolus, B. xylophilus; Ring nematodes, Criconema spp., Criconemella spp. e.g. C. xenoplax and C. ornata; and, Criconemoides spp. e.g. Criconemoides informis; Mesocriconema spp.; Stem and bulb nematodes, Ditylenchus spp. e.g. D. destructor, D. dipsaci; Awl nematodes, Dolichodorus spp.; Spiral nematodes, Heliocotylenchus multicinctus; Sheath and sheathoid nematodes, Hemicycliophora spp. and Hemicriconemoides spp.; Hirshmanniella spp.; Lance nematodes, Hoploaimus spp.; False rootknot nematodes, Nacobbus spp.; Needle nematodes, Longidorus spp. e.g. L. elongatus; Lesion nematodes, Pratylenchus spp. e.g. P. brachyurus, P. neglectus, P. penetrans, P. curvitatus, P. goodeyi;

[0676] Burrowing nema-todes, Radopholus spp. e.g. R. similis; Rhadopholus spp.; Rhodopholus spp.; Reniform nematodes, Rotylenchus spp. e.g. R. robustus, R. reniformis; Scutellonema spp.; Stubby-root nematode, Trichodorus spp. e.g. T. obtusus, T. primitivus; Paratrichodorus spp. e.g. P. minor; Stunt nematodes, Tylenchorhynchus spp. e.g. T. claytoni, T. dubius; Citrus nematodes, Tylenchulus spp. e.g. T. semipenetrans; Dagger nematodes, Xiphinema spp.; and other plant parasitic nematode species;

[0677] Insects from the order Blattodea e.g. Macrotermes spp. e.g. M. natalensis; Cornitermes cu- mulans, Procornitermes spp., Globitermes sulfureus, Neocapritermes spp. e.g. N. opacus, N. parvus; Odontotermes spp., Nasutitermes spp. e.g. N. corniger; Coptotermes spp. e.g. C. for- mosanus, C. gestroi, C. acinaciformis; Reticulitermes spp. e.g. R. hesperus, R. tibialis, R. speratus, R. flavipes, R. grassei, R. lucifugus, R. virginicus; Heterotermes spp. e.g. H. aureus, BASF SE 240867W001

[0678] B19464WO

[0679] 70

[0680] H. longiceps, H. tenuis; Cryptotermes spp. e.g. C. brevis, C. cavifrons; Incisitermes spp. e.g. I. minor, I. snyderi; Marginitermes hubbardi, Kalotermes flavicollis, Neotermes spp. e.g. N. cas- taneus, Zootermopsis spp. e.g. Z. angusticollis, Z. nevadensis, Mastotermes spp. e.g. M. dar- winiensis; Blatta spp. e.g. B. orientalis, B. lateralis; Blattella spp. e.g. B. asahinae, B. germanica; Rhyparobia maderae, Panchlora nivea, Periplaneta spp. e.g. P. americana, P. australasiae, P. brunnea, P. fuliginosa, P. japonica; Supella longipalpa, Parcoblatta pennsylvanica, Eurycotis floridana, Pycnoscelus surinamensis, Insects from the order Siphonoptera e.g. Cediopsylla simples, Ceratophyllus spp., Ctenoce- phalides spp. e.g. C. felis, C. canis, Xenopsylla cheopis, Pulex irritans, Trichodectes canis, Tunga penetrans, and Nosopsyllus fasciatus,

[0681] Insects from the order Thysanura e.g. Lepisma saccharina, Ctenolepisma urbana, and Thermobia domestica,

[0682] Pests from the class Chilopoda e.g. Geophilus spp., Scutigera spp. e.g. Scutigera coleoptrata; Pests from the class Diplopoda e.g. Blaniulus guttulatus, Julus spp., Narceus spp., Pests from the class Symphyla e.g. Scutigerella immaculata, Insects from the order Dermaptera, e.g. Forficula auricularia,

[0683] Insects from the order Collembola, e.g. Onychiurus spp., e.g. Onychiurus armatus, Pests from the order Isopoda, e.g. Armadillidium vulgare, Oniscus asellus, Porcellio scaber, Insects from the order Phthiraptera, e.g. Damalinia spp., Pediculus spp. e.g. Pediculus humanus capitis, Pediculus humanus corporis, Pediculus humanus humanus; Pthirus pubis, Haematopinus spp. e.g. Haematopinus eurysternus, Haematopinus suis; Linognathus spp. e.g. Linognathus vituli; Bovicola bovis, Menopon gallinae, Menacanthus stramineus and Solenopotes capillatus, Trichodectes spp.,

[0684] Further pest species which may be controlled by compounds I include: from the Phylum Mollusca, class Bivalvia, e.g., Dreissena spp.; class Gastropoda, e.g., Arion spp., Biomphalaria spp., Bulinus spp., Deroceras spp., Galba spp., Lymnaea spp., Oncomelania spp., Pomacea canaliclata, Succinea spp.; from the class of the helminths, e.g., Ancylostoma duodenale, Ancylostoma ceylanicum, Acylostoma braziliensis, Ancylostoma spp., Ascaris lubricoides, Ascaris spp., Brugia malayi, Brugia timori, Bunostomum spp., Chabertia spp., Clonorchis spp., Cooperia spp., Dicrocoelium spp., Dictyocaulus filaria, Diphyllobothrium latum, Dracunculus medinensis, Echinococcus granulosus, Echinococcus multilocularis, Enterobius vermicularis, Faciola spp., Haemonchus spp. e.g. Haemonchus contortus; Heterakis spp., Hymenolepis nana, Hyostrongulus spp., Loa Loa, Nematodirus spp., Oesophagostomum spp., Opisthorchis spp., Onchocerca volvulus, Ostertagia spp., Paragonimus spp., Schistosomen spp., Strongyloides fuel-leborni, Strongyloides stercora lis, Stronyloides spp., Taenia saginata, Taenia solium, Trichinella spiralis, Trichinella nativa, Trichinella britovi, Trichinella nelsoni, Trichinella pseudopsiralis, Trichostrongulus spp., Trichuris trichuria, Wuchereria bancrofti.

[0685] The compounds of the invention are particularly suitable for efficiently combating insects from the sub-order of Auchenorrhyncha, e.g. Amrasca biguttula, Empoasca spp., Nephotettix virescens, Sogatella furcifera, Mahanarva spp., Laodelphax striatellus, Nilapar-vata lugens, Diaphorina citri, Lycorma delicatula, Pentastiridus leporinus;

[0686] Lepidoptera, e.g. Helicoverpa spp., Heliothis virescens, Lobesia botrana, Ostrinia nubilalis, Plutella xylostella, Pseudoplusia includens, Scirpophaga incertulas, Spodoptera spp., BASF SE 240867W001

[0687] B19464WO

[0688] 71

[0689] Trichoplusia ni, Tuta absoluta, Cnaphalocrocis medialis, Cydia pomonella, Chilo suppressalis, Anticarsia gemmatalis, Agrotis ipsilon, Chrysodeixis includens;

[0690] True bugs, e.g. Lygus spp., Stink bugs such as Euschistus spp., Halyomorpha halys, Nezara viridula, Piezodorus guildinii, Dichelops furcatus;

[0691] Thrips, e.g. Frankliniella spp., Thrips spp., Dichromothrips corbettii;

[0692] Aphids, e.g. Acyrthosiphon pisum, Aphis spp., Myzus persicae, Rhopalosiphum spp., Schi- zaphis graminum, Megoura viciae;

[0693] Whiteflies, e.g. Trialeurodes vaporariorum, Bemisia spp.;

[0694] Coleoptera, e.g. Phyllotreta spp., Melanotus spp., Meligethes aeneus, Leptinotarsa decimlineata, Ceutorhynchus spp., Diabrotica spp., Anthonomus grandis, Atomaria linearia, Agriotes spp., Epilachna spp.;

[0695] Flies, e.g. Delia spp., Ceratitis capitate, Bactrocera spp., Liriomyza spp.;

[0696] Coccoidea, e.g. Aonidiella aurantia, Ferrisia virgate;

[0697] Anthropods of class Arachnida (Mites), e.g. Penthaleus major, Tetranychus spp.;

[0698] Nematodes, e.g. Heterodera glycines, Meloidogyne sp., Pratylenchus spp., Caenorhabditis elegans.

[0699] Animal health

[0700] The compounds of the invention are suitable for use in treating or protecting animals against infestation or infection by parasites. Therefore, the invention also relates to the use of a compound of the invention for the manufacture of a medicament for the treatment or protection of animals against infestation or infection by parasites. Furthermore, the invention relates to a method of treating or protecting animals against infestation and infection by parasites, which comprises orally, topically or parenterally administering or applying to the animals a parasiticidally effective amount of a compound of the invention.

[0701] The invention also relates to the non-therapeutic use of compounds of the invention for treating or protecting animals against infestation and infection by parasites. Moreover, the invention relates to a non-therapeutic method of treating or protecting animals against infestation and infection by parasites, which comprises applying to a locus a parasiticidally effective amount of a compound of the invention.

[0702] The compounds of the invention are further suitable for use in combating or controlling parasites in and on animals. Furthermore, the invention relates to a method of combating or con-trolling parasites in and on animals, which comprises contacting the parasites with a parasitically effective amount of a compound of the invention.

[0703] The invention also relates to the non-therapeutic use of compounds of the invention for controlling or combating parasites. Moreover, the invention relates to a non-therapeutic method of combating or controlling parasites, which comprises applying to a locus a parasiticidally effective amount of a compound of the invention.

[0704] The compounds of the invention can be effective through both contact (via soil, glass, wall, bed net, carpet, blankets or animal parts) and ingestion (e.g. baits). Furthermore, the compounds of the invention can be applied to any and all developmental stages.

[0705] The compounds of the invention can be applied as such or in form of compositions comprising the compounds of the invention. BASF SE 240867W001

[0706] B19464WO

[0707] 72

[0708] The compounds of the invention can also be applied together with a mixing partner, which acts against pathogenic parasites, e.g. with synthetic coccidiosis compounds, polyetherantibiotics e.g. Amprolium, Robenidin, Toltrazuril, Monensin, Salinomycin, Maduramicin, Lasalocid, Narasin or Semduramicin, or with other mixing partners as defined above, or in form of compositions comprising said mixtures.

[0709] The compounds of the invention and compositions comprising them can be applied orally, parenterally or topically, e.g. dermally. The compounds of the invention can be systemically or non-systemically effective.

[0710] The application can be carried out prophylactically, therapeutically or non-therapeutically. Furthermore, the application can be carried out preventively to places at which occurrence of the parasites is expected.

[0711] As used herein, the term "contacting" includes both direct contact (applying the com- pounds / compositions directly on the parasite, including the application directly on the animal or excluding the application directly on the animal, e.g. at its locus for the latter) and indirect contact (applying the compounds / compositions to the locus of the parasite). The contact of the parasite through application to its locus is an example of a non-therapeutic use of the compounds of the invention.

[0712] The term "locus" means the habitat, food supply, breeding ground, area, material or environment in which a parasite is growing or may grow outside of the animal.

[0713] As used herein, the term “parasites” includes endo- and ectoparasites. In some embodiments of the invention, endoparasites can be preferred. In other embodiments, ectoparasites can be preferred. Infestations in warm-blooded animals and fish include lice, biting lice, ticks, nasal bots, keds, biting flies, muscoid flies, flies, myiasitic fly larvae, chiggers, gnats, mosquitoes and fleas.

[0714] The compounds of the invention are especially useful for combating parasites of the following orders and species, respectively: fleas (Siphonaptera), e.g. Ctenocephalides felis, C. canis, Xenopsylla cheopis, Pulex irri-tans, Tunga penetrans, and Nosopsyllus fasciatus; cockroaches (Blattaria - Blattodea), e.g. Blattella germanica, B. asahinae, Periplaneta americana, P. japonica, P. brunnea, P. fuligginosa, P. australasiae, and Blatta orientalis; flies, mosquitoes (Diptera), e.g. Aedes aegypti, A. albopictus, A. vexans, Anastrepha ludens, Anopheles maculipennis, A. crucians, A. albimanus, A. gambiae, A. freeborni, A. leucosphyrus, A. minimus, A. quadrimaculatus, Calliphora vicina, Chrysomya bezziana, C. hominivorax, C. macellaria, Chrysops discalis, C. silacea, C. atlanticus, Cochliomyia hominivorax, Cordylobia anthropophaga, Culicoides furens, Culex pipiens, C. nigripalpus, C. quinquefasciatus, C. tarsalis, Culiseta inornata, C. melanura, Dermatobia hominis, Fannia canicularis, Gasterophilus intestinalis, Glossina morsitans, G. palpalis, G. fuscipes, G. tachinoides, Haematobia irritans, Haplodiplosis equestris, Hippelates spp., Hypoderma line-ata, Leptoconops torrens, Lucilia caprina, L. cuprina, L. sericata, Lycoria pectoralis, Mansonia spp., Musca domestica, M. stabulans, Oestrus ovis, Phlebotomus argentipes, Psorophora columbiae, P. discolor, Prosimulium mixtum, Sarcophaga spp., S. haemorrhoidalis, Simulium vittatum, Stomoxys calcitrans, Tabanus bovinus, T. atratus, T. lineola, and T. similis; lice (Phthiraptera), e.g. Pediculus humanus capitis, P. humanus humanus, Pthirus pubis, Haematopinus eurysternus, H. suis, Linognathus vituli, Bovicola bovis, Menopon gallinae, Menacanthus stramineus, and Solenopotes capillatus; ticks and parasitic BASF SE 240867W001

[0715] B19464WO

[0716] 73 mites (Parasitiformes): ticks (Ixodida), e.g. Ixodes scapularis, I. holocyclus, I. pacificus, Rhiphicephalus sanguineus, Dermacentor andersoni, D. variabilis, Amblyomma americanum, A. maculatum, Ornithodorus hermsi, O. turicata and parasitic mites (Mesostigmata), e.g. Ornithonyssus bacoti, Dermanyssus gallinae; Actinedida (Prostigmata) and Acaridida (Astigmata), e.g. Acarapis spp., Cheyletiella spp., Ornithocheyletia spp., Myobia spp., Psorergates spp., Demo-dex 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; Bugs (Het-eropterida): Cimex lectularius, C. hemipterus, Reduvius senilis, Triatoma spp., Rhodnius ssp., Panstrongylus ssp., and Arilus critatus; Anoplurida, e.g. Haematopinus spp., Linognathus spp., Pediculus spp., Phtirus spp., and Solenopotes spp.; Mallophagida (suborders Arnblycerina and Ischnocerina), e.g. Trimenopon spp., Menopon spp., Trinoton spp., Bovicola spp., Werneckiella spp., Lepikentron spp., Trichodectes spp., and Felicola spp.; Roundworms Nematoda: Wipeworms and Trichinosis (Trichosyringida), e.g. Trichinellidae (Trichinella spp.), (Trichuridae) Trichuris spp., Capillaria spp.; Rhabditida, e.g. Rhabditis spp., Strongyloides spp., Helicephalobus spp.; Strongylida, e.g. Strongylus spp., Ancylostoma spp., Necator americanus, Bunostomum spp. (Hookworm), Trichostrongylus spp., Haemonchus contortus, Ostertagia spp., Cooperia spp., Nematodirus spp., Dictyocaulus spp., Cyathostoma spp., Oesophagostomum spp., Stephanurus dentatus, Ollulanus spp., Chabertia spp., Stephanurus dentatus, Syngamus trachea, Ancylostoma spp., Uncinaria spp., Globocephalus spp., Necator spp., Metastrongylus spp., Muellerius capillaris, Protostrongylus spp., Angiostrongylus spp., Parelaphostrongylus spp., Aleurostrongylus abstrusus, and Dioctophyma renale; Intestinal roundworms (Ascaridida), e.g. Ascaris lumbricoides, Ascaris suum, Ascaridia galli, Parascaris equorum, Enterobius vermicularis (Threadworm), Toxocara canis, Toxascaris leonine, Skrjabinema spp., and Oxyuris equi; Camallanida, e.g. Dracunculus medinensis (guinea worm); Spirurida, e.g. Thelazia spp., Wuchereria spp., Brugia spp., Onchocerca spp., Dirofilari spp. a, Dipetalonema spp., Setaria spp., Elaeophora spp., Spirocerca lupi, and Habronema spp.; Thorny headed worms (Acanthocephala), e.g. Acanthocephalus spp., Macracanthorhynchus hirudinaceus and Oncicola spp.; Planarians (Plathelminthes): Flukes (Trematoda), e.g. Faciola spp., Fascioloides magna, Paragonimus spp., Dicrocoelium spp., Fasciolopsis buski, Clonorchis sinensis, Schistosoma spp., Trichobilharzia spp., Alaria alata, Paragonimus spp., and Nanocyetes spp.; Cercomeromorpha, in particular Cestoda (Tapeworms), e.g. Diphyllo-bothrium spp., Tenia spp., Echinococcus spp., Dipylidium caninum, Multiceps spp., Hymenolepis spp., Mesocestoides spp., Vampirolepis spp., Moniezia spp., Anoplocephala spp., Sirometra spp., Anoplocephala spp., and Hymenolepis spp..

[0717] The term “animal” includes warm-blooded animals (including humans) and fish. Preferred are mammals, e.g. cattle, sheep, swine, camels, deer, horses, pigs, poultry, rabbits, goats, dogs and cats, water buffalo, donkeys, fallow deer and reindeer, and also in fur-bearing animals e.g. mink, chinchilla and raccoon, birds e.g. hens, geese, turkeys and ducks and fish e.g. fresh- and salt-water fish e.g. trout, carp and eels. Particularly preferred are domestic animals, e.g. dogs or cats.

[0718] Generally, "parasiticidally effective amount" means the amount of active ingredient needed to achieve an observable effect on growth, including the effects of necrosis, death, retardation, prevention, and removal, destruction, or otherwise diminishing the occurrence and activity of the BASF SE 240867W001

[0719] B19464WO

[0720] 74 target organism. The parasiticidally effective amount can vary for the various compounds / compositions used in the invention. A parasiticidally effective amount of the compositions will also vary according to the prevailing conditions e.g. desired parasiticidal effect and duration, target species, mode of application.

[0721] Generally, it is favorable to apply the compounds of the invention in total amounts of 0.5 mg / kg to 100 mg / kg per day, preferably 1 mg / kg to 50 mg / kg per day.

[0722] For oral administration to warm-blooded animals, the compounds I may be formulated as animal feeds, animal feed premixes, animal feed concentrates, pills, solutions, pastes, suspensions, drenches, gels, tablets, boluses and capsules. In addition, the compounds I may be administered to the animals in their drinking water. For oral administration, the dosage form chosen should provide the animal with 0.01 mg / kg to 100 mg / kg of animal body weight per day of the compounds I, preferably with 0.5 mg / kg to 100 mg / kg of animal body weight per day. Alternatively, the compounds I may be administered to animals parenterally, e.g., by intraruminal, intramuscular, intravenous or subcutaneous injection. The compounds I may be dispersed or dissolved in a physiologically acceptable carrier for subcutaneous injection. Alternatively, the compounds I may be formulated into an implant for subcutaneous administration. In addition, the compounds I may be transdermally administered to animals. For parenteral administration, the dosage form chosen should provide the animal with 0.01 mg / kg to 100 mg / kg of animal body weight per day of the compounds I.

[0723] The compounds I may also be applied topically to the animals in the form of dips, dusts, powders, collars, medallions, sprays, shampoos, spot-on and pour-on formulations and in ointments or oil-in-water or water-in-oil emulsions. For topical application, dips and sprays usually contain 0.5 ppm to 5,000 ppm and preferably 1 ppm to 3,000 ppm of the compounds I. In addition, the compounds I may be formulated as ear tags for animals, particularly quadrupeds e.g. cattle and sheep.

[0724] Suitable preparations are:

[0725] - Solutions e.g. oral solutions, concentrates for oral administration after dilution, solutions for use on the skin or in body cavities, pouring-on formulations, gels;

[0726] - Emulsions and suspensions for oral or dermal administration; semi-solid preparations;

[0727] - Formulations in which the active compound is processed in an ointment base or in an oil-in- water or water-in-oil emulsion base;

[0728] - Solid preparations e.g. powders, premixes or concentrates, granules, pellets, tablets, boluses, capsules; aerosols and inhalants, and active compound-containing shaped articles. Compositions suitable for injection are prepared by dissolving the active ingredient in a suitable solvent and optionally adding further auxiliaries e.g. acids, bases, buffer salts, preservatives, and solubilizers. Suitable auxiliaries for injection solutions are known in the art. The solutions are filtered and filled sterile.

[0729] Oral solutions are administered directly. Concentrates are administered orally after prior dilution to the use concentration. Oral solutions and concentrates are prepared according to the state of the art and as described above for injection solutions, sterile procedures not being necessary. Solutions for use on the skin are trickled on, spread on, rubbed in, sprinkled on or sprayed on. Solutions for use on the skin are prepared according to the state of the art and according to what is described above for injection solutions, sterile procedures not being necessary. BASF SE 240867W001

[0730] B19464WO

[0731] 75

[0732] Gels are applied to or spread on the skin or introduced into body cavities. Gels are prepared by treating solutions which have been prepared as described in the case of the injection solutions with sufficient thickener that a clear material having an ointment-like consistency results. Suitable thickeners are known in the art.

[0733] Pour-on formulations are poured or sprayed onto limited areas of the skin, the active compound penetrating the skin and acting systemically. Pour-on formulations are prepared by dis-solving, suspending or emulsifying the active compound in suitable skin-compatible solvents or solvent mixtures. If appropriate, other auxiliaries e.g. colorants, bioabsorption-promoting substances, antioxidants, light stabilizers, adhesives are added. Suitable such auxiliaries are known in the art.

[0734] Emulsions can be administered orally, dermally or as injections. Emulsions are either of the water-in-oil type or of the oil-in-water type. They are prepared by dissolving the active compound either in the hydrophobic or in the hydrophilic phase and homogenizing this with the solvent of the other phase with the aid of suitable emulsifiers and, if appropriate, other auxiliaries e.g. colorants, absorption-promoting substances, preservatives, antioxidants, light stabilizers, viscosity-enhancing substances. Suitable hydrophobic phases (oils), suitable hydrophilic phases, suitable emulsifiers, and suitable further auxiliaries for emulsions are known in the art.

[0735] Suspensions can be administered orally or topically / dermally. They are prepared by suspending the active compound in a suspending agent, if appropriate with addition of other auxiliaries e.g. wetting agents, colorants, bioabsorption-promoting substances, preservatives, antioxidants, light stabilizers. Suitable suspending agents, and suitable other auxiliaries for suspensions including wetting agents are known in the art.

[0736] Semi-solid preparations can be administered orally or topically / dermally. They differ from the suspensions and emulsions described above only by their higher viscosity.

[0737] For the production of solid preparations, the active compound is mixed with suitable excipients, if appropriate with addition of auxiliaries, and brought into the desired form. Suitable auxiliaries for this purpose are known in the art.

[0738] The compositions which can be used in the invention can comprise generally from about 0.001 to 95% of the compound of the invention.

[0739] Ready-to-use preparations contain the compounds acting against parasites, preferably ectoparasites, in concentrations of 10 ppm to 80% by weight, preferably from 0.1 to 65% by weight, more preferably from 1 to 50% by weight, most preferably from 5 to 40% by weight. Preparations which are diluted before use contain the compounds acting against ectoparasites in concentrations of 0.5 to 90% by weight, preferably of 1 to 50% by weight.

[0740] Furthermore, the preparations comprise the compounds of formula I against endoparasites in concentrations of 10 ppm to 2% by weight, preferably of 0.05 to 0.9% by weight, very particularly preferably of 0.005 to 0.25% by weight.

[0741] Topical application may be conducted with compound-containing shaped articles e.g. collars, medallions, ear tags, bands for fixing at body parts, and adhesive strips and foils.

[0742] Generally, it is favorable to apply solid formulations which release compounds of the invention in total amounts of 10 mg / kg to 300 mg / kg, preferably 20 mg / kg to 200 mg / kg, most preferably 25 mg / kg to 160 mg / kg body weight of the treated animal in the course of three weeks. BASF SE 240867W001

[0743] B19464WO 76

[0744] Examples

[0745] The following examples illustrate the invention.

[0746] A. Preparation of Compounds

[0747] Materials: Unless otherwise noted, reagents and solvents were purchased at highest commercial quality and used without further purification.

[0748] All reactions were monitored by thin-layer chromatography (TLC) using Merck silica gel 60 F254 pre-coated plates (0.25 mm). Flash chromatography was carried out with Agela technologies silica gel (Agela techno, silica irregular 40-60um, 60A, Cat.-No. C-CS1400).

[0749] 1H NMR spectra were recorded on Bruker (500 MHz). Chemical shifts are expressed in ppm downfield from the internal solvent peaks for DMSO-de (1H; 5 = 2.50ppm) (1H; 5 = 2.50ppm) and CD3OD (1H; 5 = 3.30ppm), and J values are given in Hertz. The following abbreviations were used to explain the multiplicities: s = singlet, d = doublet, t = triplet, q = quartet, dd = double doublet, dt = double triplet, m = multiplet, br = broad. High-resolution mass spectra were measured on a JEOL JMS-T100LP.

[0750] Characterization: The compounds were characterized by coupled High Performance Liquid Chromatography with mass spectrometry (HPLC / MS).

[0751] Method 1 : UHPLC-MS on Shimadzu LCMS 2020 ESI. Analytical UHPLC column: C-18, 50mm, 4.6mm, 5micron; mobile phase: 100mM Ammonium Formate, B: Acetonitrile, Flow Rate: 1.2mL / min, Injection Vol: 1 pL in 1.50min; Gradient: 10% B to 100% B in 1.5min, Hold 100% B for 1min, 2.51 min 10% B Run time: 3min at 400°C. MS-method: ESI positive; mass range (m / z) 100- 800.

[0752] Method 2: Waters (ACQUITY-H Class UPLC. Analytical UHPLC column), Mass detector 3100: BEH-C-18, 50 mm, 2.1 mm, 1.7 micron; mobile phase: A: 0.1 % formic acid, 10% IPA in Water. B: 0.1 % formic acid in Acetonitrile C: 20 mM Ammonium Formate in water. Flow Rate: 1.2 mL / min, Injection Vol: 1 pL in 1.50 minutes; Gradient: 10 % A to 100 % B in 1.5 min, Hold 100 % B for 1 min, 2.51 min 10 % B Run time: 3 min at 400°C. MS-method: ESI positive; mass range (m / z) 100- 800.

[0753] Abbreviations used: min is minutes; ACN is acetonitrile; DCM is dichlormethane; DMF is dimethylformamide; THF is tetrahydrofuran; mL is milliliters; min is minutes; h is hour(s)

[0754] Synthesis example A: Manufacture of [4-[5-ethylsulfonyl-2-methyl-6-[5- (trifluoromethylsulfinyl)-1,3-benzoxazol-2-yl]-3-pyridyl] phenyl] methane sulfonate (1.14)

[0755] Step-1: Manufacture of 5-bromo-6-methyl-3-nitro-pyridine-2-carbonitrile

[0756] To a mixture of 5-bromo-6-methyl-3-nitro-pyridin-2-amine (2.5 g, 10.82 mmol) and copper cyanide (1.45 g, 16.23 mmol) in dimethyl sulfoxide (50 mL) was added dropwise in 10 minutes isopentyl nitrite (3.63 mL, 27.05 mmol) at 40 °C under N2. The reaction mixture was stirred at 50 °C for 4 h. The TLC monitoring showed that the starting material was consumed. Having cooled the reaction mixture up to room temperature, the reaction mixture was quenched by using ice BASF SE 240867W001

[0757] B19464WO

[0758] 77 cold water (100 mL), ethyl acetate (200 mL) and brine solution (50 mL). While precipitate occurred, the mixture was then filtered over a pad of celite, washed with ethyl acetate (200 mL). The filtrate aqueous phase was separated and extracted with ethyl acetate. To a mixture of 5- bromo-6-methyl-3-nitro-pyridin-2-amine (2.5 g, 10.82 mmol) and copper cyanide (1.45 g, 16.23 mmol) in dimethyl sulfoxide (50 mL) was added dropwise in 10 minutes isopentyl nitrite (3.63 mL, 27.05 mmol) at 40 °C under N2 gas. The reaction mixture was stirred at 50 °C for 4 h. While monitoring by TLC indicated disappearance of the starting material, the reaction mixture was cooled up to room temperature then reaction mixture quenched by using ice cold water (100 mL), ethyl acetate (200 mL) and brine solution (50 mL). A precipitate occurred, the mixture was filtered over a pad of celite, washed with ethyl acetate (200 mL). The filtrate aqueous phase was separated and extracted with ethyl acetate. The combined organic layers were washed with brine solution, dried over anhydrous sodium sulfate, filtered and concentrated under vacuum to give crude material. The crude was purified through a flash chromatography over silica gel (18% EtOAc / n-heptane as an eluent) to obtain the desired product (0.80 g, 30% yield).1H NMR (300 MHz, DMSO-d6) 5 9.04 (s, 1 H), 2.75 (s, 3H). LC-MS: mass calculated for Cy^BrNsCh [M]+ 240.9, found: 240 (M-H).

[0759] Step-2: Manufacture of 5-bromo-3-ethylsulfanyl-6-methyl-pyridine-2-carbonitrile Having dissolved 5-bromo-6-methyl-3-nitro-pyridine-2-carbonitrile (0.750 g, 3.11 mmol) in anhydrous THF (27 mL), the reaction mixture was cooled to 0 °C. In a separate vial, sodium ethane thiolate was taken (0.413 g, 4.67 mmol) and dissolved in water (3.0 mL) at 0 °C then added into the reaction mixture dropwise at 0 °C -10 °C under N2 atmosphere. The mixture was stirred at 10 °C for 0.5 h. The mixture was quenched with ice cooled water (100 mL) and the aqueous layer was separated and extracted twice with ethyl acetate (200 mL). The organic layers were combined, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The crude was purified through a flash chromatography over silica gel (12 % EtOAc / n-heptane as an eluent) to get the anticipated compound (0.6 g, 72% yield).1H NMR (500 MHz, DMSO-d6) 5 8.32 (s, 1 H), 3.20 (q, J = 7.3 Hz, 2H), 2.57 (s, 3H), 1.25 (t, J = 7.3 Hz, 3H) LC-MS: mass calculated for C9H9BrN2S [M]+255.9, found: 257.2 (M+H).

[0760] Step-3: Manufacture of 2-(5-bromo-3-ethylsulfanyl-6-methyl-2-pyridyl)-5- (trifluoromethylsulfanyl)-1,3-benzoxazole

[0761] In a 40 ml Microwave vial, 5-bromo-3-ethylsulfanyl-6-methyl- pyridine-2-carbonitrile (0.4 g, 1.56 mmol, 1 eq) and 2-amino-4-(trifluoromethylsulfanyl) phenol (0.325 g, 1.56 mmol) were dissolved in 4-chlorobenzene (10 mL). Copper(ll) trifluoromethanesulfonate (0.113 g, 0.31 mmol) was added in to the reaction mixture and the mixture was heated at 140 °C for 1 h. After monitor the reaction mixture by TLC and LCMS, the mixture was quenched with water (50 mL) and ethyl acetate (80 mL), the aqueous layer was extracted and separated twice with ethyl acetate (100 mL). The organic layer washed with sat NaHCOs solution (50 mL), then combined organic layers was dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The crude was purified through a flash chromatography over silica gel (25% EtOAc / n-heptane as an eluent) to obtain the desired product (0.45 g, 63% yield).1H NMR (500 MHz, DMSO-de) 5 8.34 (d, J = 1.8 Hz, 1 H), 8.15 (s, 1 H), 8.06 (d, J = 8.5 Hz, 1 H), 7.86 (dd, J = 8.5, 1.8 Hz, 1 H), 3.14 (q, J = 7.4 Hz, 2H), 2.66 (s, 3H), 1.30 (t, J = 7.3 Hz, 3H). LC-MS: mass calculated for C16H12BrF3N2OS2[M]+ 450, found: 451 (M+H). BASF SE 240867W001

[0762] B19464WO

[0763] 78

[0764] Step-4: Manufacture of 2-(5-bromo-3-ethylsulfonyl-6-methyl-2-pyridyl)-5-

[0765] (trifluoromethylsulfinyl)-1,3-benzoxazole (1.20)

[0766] To a stirred solution of 2-(5-bromo-3-ethylsulfanyl-6-methyl-2-pyridyl)-5-(trifluoromethylsulfanyl)- 1 ,3-benzoxazole (0.3 g, 0.67 mmol, 1.0 eq) in dichloromethane (15 mL), 77% of m- chloroperbenzoic acid (0.748 g, 3.34 mmol) was added at 0 °C. The reaction mixture was then stirred overnight at room temperature. After monitoring the reaction mixture by TLC and LCMS, the reaction mixture was poured to a mixed solution (50 mL) of a saturated aqueous solution of sodium bicarbonate and a saturated aqueous solution of sodium thiosulfate (1 :1), followed by extraction with dichloromethane (100 mL). The obtained organic layer was washed with brine solution (30 mL), dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The crude was purified through a flash chromatography over silica gel (40% EtOAc / n-heptane as an eluent) to the anticipated compound (0.29 g, 86% yield).1H NMR (300 MHz, DMSO-d6) 6 8.67 (s, 1H), 8.53 (d, J = 1.7 Hz, 1 H), 8.30 (dd, J = 8.7, 0.6 Hz, 1H), 8.14 - 8.05 (m, 1 H), 3.92 (q, J = 7.4 Hz, 2H), 2.79 (s, 3H), 1.27 (q, J = 7.3 Hz, 3H). LC-MS: mass calculated for Ci6Hi2BrF3N2O4S2[M]+ 495.9, found: 497 (M+H).

[0767] Step-5: Manufacture of [4-[5-ethylsulfonyl-2-methyl-6-[5-(trifluoromethylsulfinyl)-1,3- benzoxazol-2-yl]-3-pyridyl] phenyl] methane sulfonate (1.14)

[0768] To a stirred solution of 2-(5-bromo-3-ethylsulfonyl-6-methyl-2-pyridyl)-5-(trifluoromethylsulfinyl)- 1 ,3-benzoxazole (0.04 g, 0.06 mmol) and (4-methylsulfonyloxyphenyl) boronic acid (0.018 g, 0.08 mmol) in dry 1 ,4 dioxane (5.0 mL) was added K2COs (0.027 g,0.19 mmol) in 1.0 mL of H2O. Having purged the reaction mixture using N2gas for 5 min, then added [1,1' - bis(diphenylphosphino)ferrocene]dichloropalladium(ll) (0.007 g, 0.01 mmol), purged the reaction mixture for further 3-4 min then heated to 100 °C for 4 h. The progress of the reaction was monitored by TLC and LCMS. After the reaction was completed, it was added with 20 mL of water and was extracted with 80 mL of EtOAc (40 mL x 2), the combined organic layer was dried over Na2SO4, concentrated under reduced pressure to get the crude product which was purified by column chromatography using 30% EtOAc in n-Heptane as an eluent to afford the desired compound as solid (0.014g, 36% yield).1H NMR (300 MHz, DMSO-d6) 6 8.54 (s, 1 H), 8.31 (d, J = 9.5 Hz, 2H), 8.10 (d, J = 8.7 Hz, 1 H), 7.76 (d, J = 8.6 Hz,2H), 7.56 (d, J = 8.6 Hz, 2H), 3.91 (q, J = 7.4 Hz, 2H), 3.48 (s, 3H), 2.67 (s, 3H), 1.28 (q, J = 7.4 Hz, 3H). LC-MS: mass calculated for C23Hi9F3N2O?S3 [M]+ 588, found: 589.2 (M+H).

[0769] Manufacture of 1-[4-[5-ethylsulfonyl-2-methyl-6-[5-(trifluoromethylsulfinyl)-1,3- benzoxazol-2-yl]-3-pyridyl] phenyl] cyclopropane carbonitrile (1.21) BASF SE 240867W001

[0770] B19464WO

[0771] To a stirred solution of 2-(5-bromo-3-ethylsulfonyl-6-methyl-2-pyridyl)-5-(trifluoromethylsulfinyl)- 1 ,3-benzoxazole (0.150 g, 0.31 mmol) and [4-(1-cyanocyclopropyl)phenyl]boronic acid (0.076 g, 0.41 mmol) in dry 1,4 dioxane (8.0 mL) was added K2CO3 (0.129 g ,0.94 mmol) in 2 mL H2O. The reaction mixture was purged using N2 gas for 5 min then [1,1' -bis(diphenylphosphino) ferrocene]dichloropalladium(ll) (0.023 g, 0.03 mmol), was added. Having purged the reaction mixture for further 3-4 min, it was then heated to 100 °C for 4 h. The progress of the reaction was monitored by TLC and LCMS. After the reaction was completed, it was added with 20 mL of water and was extracted with 80 mL of EtOAc (40mL x 2), the combined organic layer was dried over Na2SO4, concentrated under reduced pressure to get the crude product which was purified by column chromatography using 30% EtOAc in n-Heptane as an eluent to afford the desired compound (0.128g, 78% yield).1H NMR (300 MHz, DMSO-d6) 5 8.53 (s, 1H), 8.35 - 8.22 (m, 2H), 8.10 (d, J = 8.7 Hz, 1 H), 7.74 - 7.60 (m, 2H), 7.60 - 7.47 (m, 2H), 3.91 (q, J = 7.4 Hz, 2H), 2.66 (s, 3H), 1.90 - 1.80 (m, 2H), 1.73 - 1.58 (m, 2H), 1.28 (q, J = 6.3 Hz, 3H). LC-MS: mass calculated for C26H20F3N3O4S2 [M]+ 559.6, found: 560.3 (M+H).

[0772] Manufacture of 1-[4-[5-ethylsulfonyl-2-methyl-6-[5-(trifluoromethylsulfinyl)-1 ,3-

[0773] To a stirred solution of 1-[4-[5-ethylsulfonyl-2-methyl-6-[5-(trifluoromethylsulfinyl)-1,3- benzoxazol-2-yl]-3-pyridyl]phenyl]cyclopropanecarbonitrile (0.080 g, 0.14 mmol) in toluene (5.0 mL) added acetaldoxime (0.033 g, 0.57 mmol) followed by tris(triphenylphosphine)rhodium(l) chloride (0.026 g, 0.03 mmol) then reaction mixture heated to 110 °C for 18 h. The progress of the reaction was monitored by TLC and LCMS. After the reaction was completed, it was added with 30 mL of water and was extracted with 80 mL of EtOAc (40mL x 2), the combined organic layer was dried over Na2SO4, concentrated under reduced pressure to get the crude product which was purified by column chromatography using 80% EtOAc in n-Heptane as an eluent to afford the desired compound as solid (0.053 gm, 59% yield).1H NMR (300 MHz, DMSO-de): 5 8.54 (s, 1 H), 8.35 - 8.23 (m, 2H), 8.10 (d, J = 8.7 Hz, 1 H), 7.68 - 7.49 (m, 4H), 7.14 (s, 1 H), 6.38 (s, 1H), 3.92 (q, J = 7.3 Hz, 2H), 2.70 (s, 3H), 1.39 (q, J = 3.8 Hz, 2H), 1.28 (q, J = 7.6 Hz, 3H), 1.05 (q, J = 3.9 Hz, 2H). LC-MS: mass calculated for C26H22F3N3O5S2 [M]+ 577.6, found: 578.2 (M+H).

[0774] Manufacture of 2-[5-[4-(2-cyclopropylethynyl) phenyl]-3-ethylsulfonyl-6-methyl-2-pyridyl]~ 5-(trifluoromethylsulfinyl)-1,3-benzoxazole (1.40) BASF SE 240867W001

[0775] B19464WO

[0776] To a stirred solution of 2-(5-bromo-3-ethylsulfonyl-6-methyl-2-pyridyl)-5-(trifluoromethylsulfinyl)- 1 ,3-benzoxazole (0.076 g, 0.15 mmol) in dry THF (5.0 mL) at RT was added N- ethyldiisopropylamine (0.059 mL, 0.38 mmol) and ethynyl cyclopropane (0.020 g, 0.31 mmol). Reaction mixture was degassed with N2 gas for 5 mins followed by addition of 1 ,1' - bis(diphenylphosphino)ferrocene] dichloropalladium(ll) (0.011g, 0.015 mmol) and copper (I) iodide (0.001g, 0.02 mmol), degassing was continued for another 5 mins. After the degassing was completed reaction mixture was allowed to stir at RT for 15 mins. The progress of the reaction was monitored by TLC. After the reaction was completed, it was added with 30 mL of water and compound was extracted with 100 mL of EtOAc (50 mL x 2), the combined organic layer was dried over Na2SO4, concentrated under reduced pressure to get the crude product which was purified by column chromatography using 30% EtOAc in n-heptane as an eluent to afford desired product as beige solid (0.045 g, 59% yield).1H NMR (300 MHz, DMSO-de) 5 8.51 (d, J = 1.7 Hz, 1 H), 8.37 - 8.24 (m, 2H), 8.13 - 8.04 (m, 1 H), 3.90 (q, J = 7.4 Hz, 2H), 2.73 (s, 3H), 1.81 - 1.66 (m, 1 H), 1.26 (t, J = 7.4 Hz, 4H), 1.03 (dt, J = 8.1 , 3.0 Hz, 2H), 0.93 (dt, J = 4.9, 3.0 Hz, 2H). LC-MS: mass calculated for C21H17F3N2O4S2 [M]+ 482, found: 483 (M+H).

[0777] Synthesis example B: Manufacture of [4-[5-ethylsulfonyl-2-methyl-6-[5- (trifluoromethylsulfonimidoyl)-l ,3-benzoxazol-2-yl]-3-pyridyl]phenyl] methanesulfonate (I.

[0778] Step 1 : Manufacture of 2-(5-bromo-3-ethylsulfonyl-6-methyl-2-pyridyl)-5-

[0779] 2-(5-bromo-3-ethylsulfanyl-6-methyl-2-pyridyl)-5-(trifluoromethylsulfanyl)-1 ,3-benzoxazole (0.0175 g, 0.39 mmol) was dissolved in dichloromethane (10.0 mL), and the solution was cooled to 0° C. and stirred for 5 min, 77% m-chloroperbenzoic acid (0.262 g ,1.17 mmol) was added in to the, reaction mixture a. The reaction mixture was stirred overnight at 0 °C to room temperature. After monitoring the reaction mixture by TLC and LCMS, the reaction mixture was poured to a mixed solution (50 mL) of a saturated aqueous solution of sodium bicarbonate and a saturated aqueous solution of sodium thiosulfate (1 :1), followed by extraction with dichloromethane (60 mL). The obtained organic layer was washed with brine solution (30 mL), BASF SE 240867W001

[0780] B19464WO dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The crude was purified through a flash chromatography over silica gel (40% EtOAc / n-heptane as an eluent) to get the desired compound as solid (0.115 gm, 82% yield).1H NMR (300 MHz, DMSO- d6) 5 8.65 (s, 1 H), 8.38 (d, J = 1.8 Hz, 1 H), 8.11 (dd, J = 8.6, 0.6 Hz, 1 H), 7.92 (dd, J = 8.6, 1.8 Hz, 1 H), 3.92 (q, J = 7.4 Hz, 2H), 2.79 (s, 3H), 1.28 (t, J = 7.4 Hz, 3H). LC-MS: mass calculated for Ci6Hi2BrF3N2O3S2[M]+ 482, found 483: (M+H).

[0781] Step-2: [4-[5-ethylsulfonyl-2-methyl-6-[5-(trifluoromethylsulfanyl)-1,3-benzoxazol-2-yl]-3- pyridyl]phenyl] methanesulfonate (1.13)

[0782] To a stirred solution of 2-(5-bromo-3-ethylsulfonyl-6-methyl-2-pyridyl)-5-(trifluoromethylsulfinyl)-

[0783] 1.3-benzoxazole (0.124 g, 0.26 mmol,1 eq) and (4-methylsulfonyloxyphenyl) boronic acid (0.072 g, 0.33 mmol) in dry 1 ,4 dioxane (5.0 mL) was added K2CO3(0.106, 0.770 mmol) in 1.0 mL of H2O. Having purged the reaction mixture using N2gas for 5 min, [1 ,1' - bis(diphenylphosphino)ferrocene]dichloropalladium(ll) (0.019 g, 0.03 mmol) was added, purged again for further 3-4 min then heated to 100 °C for 4 h. The progress of the reaction was monitored by TLC and LCMS. After the reaction was completed, it was added with 20 mL of water and was extracted with 80 mL of EtOAc (40 mL x 2), the combined organic layer was dried over Na2SO4, concentrated under reduced pressure to get the crude product which was purified by column chromatography using 30% EtOAc in n-Heptane as an eluent to obtain the desired product as solid (0.120 g, 79% yield).1H NMR (500 MHz, DMSO-d6) 5 8.39 (d, J = 1.8 Hz, 1 H), 8.28 (s, 1 H), 8.12 (d, J = 8.5 Hz, 1 H), 7.92 (dd, J = 8.5, 1.8 Hz, 1 H), 7.83 - 7.72 (m, 2H), 7.59 - 7.53 (m, 2H), 3.90 (q, J = 7.4 Hz, 2H), 3.47 (s, 3H), 2.67(s, 3H), 1 .29 (t, J = 7.4 Hz, 3H). LC-MS: mass calculated for C23Hi9F3N2OeS3[M]+ 572.0, found: 573.3 (M+H).

[0784] Step-3: Manufacture of [4-[5-ethylsulfonyl-2-methyl-6-[5-(trifluoromethylsulfonimidoyl)-

[0785] 1.3-benzoxazol-2-yl]-3-pyridyl]phenyl] methanesulfonate (1.25)

[0786] To a solution of Phl(OAc)2(0.0158 g, 0.47 mmol, 4.0 eq,) and ammonium carbamate (0.026 g, 0.31 mmol, 2.5 eq) in 2,2,3,3,4,4,5,5-octafluoro-1-pentanol (5.0 mL) was added [4-[5- ethylsulfonyl-2-methyl-6-[5-(trifluoromethylsulfanyl)-1 ,3-benzoxazol-2-yl]-3-pyridyl]phenyl] methanesulfonate (0.078 g, 0.12 mmol). The reaction mixture was stirred at room temperature for 18 h. The progress of the reaction was monitored by TLC and LCMS. After the reaction was completed, it was added with of saturated NaHCOs solution (40 mL) and was extracted with 80 mL of EtOAc (40 mL x 2), the combined organic layer was dried over Na2SO4, concentrated under reduced pressure to get the crude product which was purified by column chromatography using 60% EtOAc in n-Heptane as an eluent to afford the desired compound (0.024 g, 32% yield).1H NMR (300 MHz, DMSO-d6) 5 8.65 (s, 1 H), 8.31 (d, J = 4.1 Hz, 3H), 7.85 - 7.72 (m, 2H), 7.56 (d, J = 8.6 Hz, 2H), 7.12 (s, 1 H), 3.92 (q, J = 7.4 Hz, 2H), 3.48 (s, 3H), 2.67 (s, 3H), 1 .29 (t, J = 7.4 Hz, 3H). LC-MS: mass calculated for C23H20F3N3O7S3[M]+ 603, found: 604 (M+H). BASF SE 240867W001

[0787] B19464WO 82 Synthesis example C: Manufacture of 3-cyclopropyl-5-ethylsulfonyl-6-[5- (trifluoromethylsulfonyl)-1,3-benzoxazol-2-yl]pyridine-2-carbonitrile (I. 37)

[0788] Step-1 : Manufacture of 2-(5-bromo-3-ethylsulfonyl-2-pyridyl)-5-(trifluoromethylsulfinyl)- 1 ,3-benzoxazole

[0789] To a stirred solution of 5-bromo-3-ethylsulfonyl-N-[2-hydroxy-5-(trifluoromethylsulfinyl)phenyl] pyridine-2-carboxamide (3.0 g, 5.98 mmol) in xylene (30 mL) was added p-toluene sulphonic acid monohydrate (2.846 g, 14.961 mmol). The reaction mixture was heated at 155 °C using Dean-Stark apparatus for 7 hours. The progress of the reaction was monitored by TLC. After the reaction was completed, it was added into 150 mL of ice-cold water and 150 mL of EtOAc, it was then neutralized using solid NaHCCh and the layer was separated, compound was extracted with EtOAc (100 mL). The combined organic layer was washed with brine solution then dried over sodium sulfate, concentrated under reduced pressure to get the crude product which was purified by column chromatography using 60% EtOAc in n-heptane as an eluent to afford 2-(5-bromo-3-ethylsulfonyl-2-pyridyl)-5-(trifluoromethylsulfinyl)-1 ,3-benzoxazole as beige solid (2.57g, 88.8% yield).1H NMR (300 MHz, DMSO-d6) 6 9.32 (d, J = 2.1 Hz, 1 H), 8.76 (d, J = 2.1 Hz, 1 H), 8.57 - 8.51 (m, 1 H), 8.34 - 8.26 (m, 1 H), 8.14 - 8.06 (m, 1 H), 3.96 (q, J = 7.4 Hz, 2H), 1.30 (t, J = 7.4 Hz, 3H). LC-MS: mass calculated for Ci5HioBrF3N204S2 [M]+ 483.27, found: 485.0 (M+2).

[0790] Step-2: Manufacture of 2-(5-cyclopropyl-3-ethylsulfonyl-2-pyridyl)-5- (trifluoromethylsulfinyl)-1,3-benzoxazole

[0791] To a stirred solution of 2-(5-bromo-3-ethylsulfonyl-2-pyridyl)-5-(trifluoromethylsulfinyl)-1 ,3- benzoxazole (0.7 g, 1.45 mmol) in a mixture of 1 ,4-dioxane (20 mL) and H2O (4 mL) was added potassium carbonate (0.5 g, 3.62 mmol) and cyclopropylboronic acid (0.249 g, 2.9 mmol). The reaction mixture was degassed with N2 gas for 10 mins followed by addition of [1 ,1' - bis(diphenylphosphino)ferrocene]dichloropalladium(ll) (0.074 g, 0.1 mmol) and degassing was continued for another 5 mins. After the degassing was completed, the reaction mixture was heated at 120 °C in microwave for 2 h. The progress of the reaction was monitored by TLC. After the reaction was completed, it was added with 50 mL of water and compound was BASF SE 240867W001

[0792] B19464WO 83 extracted with 60 mL of EtOAc (30 mL x 2), the combined organic layer was dried over Na2SC>4, concentrated under reduced pressure to get the crude product which was purified by column chromatography using 60% EtOAc in n-heptane as an eluent to afford desired product as beige solid (0.6 g, 93% yield).1H NMR (300 MHz, DMSO-d6) 5 8.90 (d, J = 2.1 Hz, 1 H), 8.50 (s, 1 H), 8.27 (d, J = 8.6 Hz, 1 H), 8.18 (d, J = 2.1 Hz, 1 H), 8.08 (d, J = 8.6 Hz, 1 H), 3.88 (q, J = 7.4 Hz, 2H), 2.31 (m, 1 H), 1.37 - 1.15 (m, 6H), 1.10 - 0.99 (m, 2H). LC-MS: mass calculated for C18H15F3N2O4S2 [M]+ 444.44, found: 445.2 (M+1).

[0793] Step-3: Manufacture of 2-(5-cyclopropyl-3-ethylsulfonyl-1-oxido-pyridin-1-ium-2-yl)-5- (trifluoromethylsulfonyl)-1,3-benzoxazole

[0794] To a stirred solution of 2-(5-cyclopropyl-3-ethylsulfonyl-2-pyridyl)-5-(trifluoromethylsulfinyl)-1 ,3- benzoxazole (1.4 g, 3.15 mmol) in dry TFA (10 mL) at RT was added 30 % hydrogen peroxide (1 .42 g, 12.6 mmol) reaction mixture was allowed to stir at 70 °C for 2 h. The progress of the reaction was monitored by TLC and LCMS. After the reaction was completed, the reaction was cooled and the mixture then added with 100 mL of sat. NaHCCh solution and ethyl acetate (100 mL). The mixture was stirred vigorously then separated the layer, aqueous phase was extracted with 100 mL ethyl acetate, the combined organic layer was dried over Na2SO4, concentrated under reduced pressure to get desired product as solid (1.45 g, 97% yield).1H NMR (300 MHz, DMSO-d6) 5 8.84 (d, J = 1 .8 Hz, 1 H), 8.72 (d, J = 1 .5 Hz, 1 H), 8.45 - 8.29 (m, 2H), 7.75 (d, J = 1.5 Hz, 1 H), 3.59 (q, J = 7.3 Hz, 2H), 2.22 (m, 1 H), 1.27 - 1.19 (m, 5H), 1.12 - 1.02 (m, 2H). LC-MS: mass calculated for C18H15F3N2O6S2 [M]+ 476, found 477 (M+H).

[0795] Step-4: Manufacture of 2-(6-chloro-5-cyclopropyl-3-ethylsulfonyl-2-pyridyl)-5- (trifluoromethyl sulfonyl)-1,3-benzoxazole

[0796] To a stirred solution of 2-(5-cyclopropyl-3-ethylsulfonyl-1-oxido-pyridin-1-ium-2-yl)-5- (trifluoromethylsulfonyl)-1 ,3-benzoxazole (1.4 g, 2.35 mmol) under N2 atmosphere, phosphoryl trichloride (7.2 g, 47.02 mmol) was added at RT then reaction mixture was allowed to stir at 110 °C for 1 h. The progress of the reaction was monitored by TLC and LCMS. After the reaction was completed, the reaction mixture was cooled and then quenched with 100 mL of sat. NaHCOs solution slowly and extracted with ethyl acetate (200 mL). The layer was separated, the aqueous phase was extracted again with 100 mL ethyl acetate, the combined organic layer was dried over Na2SC>4, concentrated under reduced pressure to get desired product as solid (0.70 g, 60% yield).1H NMR (300 MHz, DMSO-d6) 5 8.85 (d, J = 1.9 Hz, 1 H), 8.46 - 8.30 (m, 2H), 8.02 (s, 1 H), 3.93 (q, J = 7.4 Hz, 2H), 2.40 - 2.29 (m, 1 H), 1.34 - 1.21 (m, 5H), 1.09 - 0.98 (m, 2H). LC-MS: mass calculated for C18H14CIF3N2O5S2 [M]+ 494, found: 495 (M+H).

[0797] Step-5: Manufacture of 3-cyclopropyl-5-ethylsulfonyl-6-[5-(trifluoromethylsulfonyl)-1,3- benzoxazol-2-yl]pyridine-2-carbonitrile (1.37)

[0798] To a stirred solution of 2-(6-chloro-5-cyclopropyl-3-ethylsulfonyl-2-pyridyl)-5- (trifluoromethylsulfonyl)-1 ,3-benzoxazole (0.05 g, 0.1 mmol) in DMF (1.0 mL) was added zinc cyanide (0.018 g, 0.15 mmol). Reaction mixture was degassed with N2 gas for 5 mins followed by addition of tetrakis(triphenylphosphine)palladium (0.012 g, 0.01 mmol) and degassing was BASF SE 240867W001

[0799] B19464WO

[0800] 84 continued for another 5 mins. After the degassing was completed reaction mixture was heated at 120 °C for 2 h. The progress of the reaction was monitored by TLC. After the reaction was completed, it was added with 30 mL of water and compound was extracted with 80 mL of EtOAc (40 mL x 2), the combined organic layer was dried over sodium sulphate, concentrated under reduced pressure to get the crude product which was purified by column chromatography using 50% EtOAc in n-heptane as an eluent to afford desired product as white solid (0.015 g, 30.4% yield).1H NMR (300 MHz, DMSO-d6) 5 8.86 (d, J = 1.9 Hz, 1 H), 8.42 (dd, J = 8.8, 0.7 Hz, 1 H), 8.35 (dd, J = 8.9, 1.9 Hz, 1H), 8.14 (s, 1 H), 3.97 (q, J = 7.4 Hz, 2H), 2.46 - 2.37 (m, 1 H), 1.45 - 1.36 (m, 2H), 1.29 (t, J = 7.4 Hz, 3H), 1.22 - 1.15 (m, 2H). LC-MS: mass calculated for C19H14F3N3O5S2 [M]+ 485.03, found: 486.3 (M+1).

[0801] Manufacture of 2-(5-cyclopropyl-3-ethylsulfonyl-6-methyl-2-pyridyl)-5- (trifluoromethylsulfonyl)-1,3-benzoxazole (1.1)

[0802] To a stirred solution of 2-(6-chloro-5-cyclopropyl-3-ethylsulfonyl-2-pyridyl)-5- (trifluoromethylsulfonyl)-1 ,3-benzoxazole (0.062 g, 0.13 mmol) in a mixture of 1,4-dioxane(4.0 mL) and H2O (0.4 mL) was added potassium carbonate (0.043 g, 0.31 mmol) and 2,4,6- trimethyl-1,3,5,2,4,6-trioxatriborinane (50% in THF, 0.094 mL, 0.38 mmol). The reaction mixture was degassed with N2 gas for 5 mins followed by addition of [1,T - bis(diphenylphosphino)ferrocene]dichloropalladium(ll) (0.006 g, 0.01 mmol) and degassing was continued for another 5 mins. After the degassing was completed, the reaction mixture was heated at 80 °C for 2 h. The progress of the reaction was monitored by TLC. After the reaction was completed, it was added with 20 mL of water and compound was extracted with 20 mL of EtOAc (10 mL x 2), the combined organic layer was dried over Na2SO4, concentrated under reduced pressure to get the crude product which was purified by column chromatography using 60% EtOAc in n-heptane as an eluent to afford desired product as white solid (0.05 g, 84% yield).1H NMR (300 MHz, DMSO-d6) 5 8.79 (d, J = 1.7 Hz, 1 H), 8.40 - 8.35 (m, 1 H), 8.30 (dd, J = 8.7, 1.8 Hz, 1H), 7.89 (s, 1 H), 3.82 (q, J = 7.6 Hz, 2H), 2.78 (s, 3H), 2.25 - 2.14 (m, 1 H), 1.23 (t, J = 7.4 Hz, 3H), 1.20 - 1.10 (m, 2H), 0.93 - 0.83 (m, 2H). LC-MS: mass calculated for C19H17F3N2O5S2 [M]+ 474.5, found: 475.2 (M+1).

[0803] Manufacture of 3-cyclopropyl-5-ethylsulfonyl-N,N-dimethyl-6-[5-(trifluoromethylsulfonyl)- 1 ,3-benzoxazol-2-yl]pyridin-2-amine (1.34)

[0804] To a stirred solution of 2-(6-chloro-5-cyclopropyl-3-ethylsulfonyl-2-pyridyl)-5-

[0805] (trifluoromethylsulfonyl)-1 ,3-benzoxazole (0.05 g, 0.10 mmol) in dry DMF ( 1.0 mL) under N2 BASF SE 240867W001

[0806] B19464WO

[0807] 85 atmosphere, added N-methylmethanamine, hydrochloride (0.033 g, 0.4041 mmol) followed by potassium carbonate (0.028 g, 0.20 mmol), reaction mixture was allowed to stir at 110 °C for 1 h. The progress of the reaction was monitored by TLC and LCMS. While the reaction was complete, the reaction mixture was cooled and then quenched it with 20 mL of water and extracted it ethyl acetate (80 mL), separated the layer, aqueous phase was extracted with 40 mL ethyl acetate, the combined organic layer was dried over Na2SO4, concentrated under reduced pressure to get desired product as solid (0.040 g, 78% yield).1H NMR (300 MHz, DMSO-d6) 5 8.77 (d, J = 1.8 Hz, 1 H), 8.41 - 8.24 (m, 2H), 7.72 (d, J = 0.9 Hz, 1 H), 3.66 (q, J = 7.4 Hz, 2H), 3.23 (s, 6H), 2.17 (m, 1 H), 1.22 (t, J = 7.4 Hz, 3H), 1.16 - 1.01 (m, 2H), 0.88 - 0.77 (m, 2H). LC-MS: mass calculated for C20H20F3N3O5S2 [M]+ 503, found: 504 (M+H).

[0808] Manufacture of [4-[3-cyclopropyl-5-ethylsulfonyl-6-[5-(trifluoromethylsulfonyl)-1 ,3- benzoxazol-2-yl]-2-pyridyl]phenyl] methanesulfonate (1.36)

[0809] To a stirred solution of 2-(6-chloro-5-cyclopropyl-3-ethylsulfonyl-2-pyridyl)-5- (trifluoromethylsulfonyl)-1 ,3-benzoxazole (0.08 g, 0.1617 mmol) in dry dioxane (5.0 mL) under N2 atmosphere, added 4-methylsulfonyloxyphenyl)boronic acid (0.052 g, 0.2425 mmol) followed by potassium carbonate (0.045 g, 0.3032 mmol) in 1.0 mL of water, degassed the reaction mixture using N2 gas for 5 min then added Pd(dppf)Ch (12 mg, 0.016 mmol) reaction mixture was allowed to stir at 110 °C for 1 h. The progress of the reaction was monitored by TLC and LCMS. While the reaction was complete, the reaction mixture was cooled and then quenched with 20 mL of water and extracted with ethyl acetate (80 mL), separated the layer, aqueous phase concentrated under reduced pressure to get desired product as solid (0.040 g, 78% yield).1HNMR (300 MHz, DMSO-d6) 5 8.82 (d, J = 1.9 Hz, 1 H), 8.38 (d, J = 9.0 Hz, 1 H), 8.31 (dd, J = 8.8, 1.9 Hz, 1 H), 8.03 (s, 1 H), 7.95 - 7.84 (m, 2H), 7.60 - 7.49 (m, 2H), 3.94 (q, J = 7.3 Hz, 2H), 3.47 (s, 3H), 2.23 - 2.08 (m, 1 H), 1.31 (t, J = 7.4 Hz, 3H), 1.24 - 1.11 (m, 2H), 1.07 - 0.95 (m, 2H). LC-MS: mass calculated for C25H21F3N2O8S3 [M]+ 630, found: 631 (M+H).

[0810] Manufacture of 2-(5-cyclopropyl-3-ethylsulfonyl-6-ethynyl-2-pyridyl)-5-(trifluoromethyl sulfonyl)-1 ,3-benzoxazole (1.38) BASF SE 240867W001

[0811] B19464WO

[0812] 86

[0813] Step-1 : Manufacture of 2-[3-cyclopropyl-5-ethylsulfonyl-6-[5-(trifluoromethylsulfonyl)-1,3- benzoxazol-2-yl]-2-pyridyl]ethynyl-trimethyl-silane

[0814] To a stirred solution of 2-(6-chloro-5-cyclopropyl-3-ethylsulfonyl-2-pyridyl)-5- (trifluoromethylsulfonyl)-1 ,3-benzoxazole (0.1 g, 0.2 mmol) in dry THF (5.0 mL) at RT was added triethylamine (0.084 mL, 0.61 mmol) and trimethylsilyl acetylene (0.06 g, 0.061 mmol). Reaction mixture was degassed with N2 gas for 5 mins followed by addition of dichlorobis(triphenylphosphine)palladium(ll) (0.014 g, 0.02 mmol) and copper(l) iodide (0.004 g, 0.02 mmol), degassing was continued for another 5 mins. After the degassing was completed reaction mixture was allowed to stir at RT for 2 h. The progress of the reaction was monitored by TLC. After the reaction was completed, it was added with 30 mL of water and compound was extracted with 60 mL of EtOAc (30 mL x 2), the combined organic layer was dried over Na2SC>4, concentrated under reduced pressure to get the crude product which was purified by column chromatography using 30% EtOAc in n-Heptane as an eluent to afford desired product as beige solid (0.05 g, 44.45% yield).1H NMR (300 MHz, DMSO-d6) 5 8.82 (d, J = 1.9 Hz, 1 H), 8.40 (dd, J = 8.8, 0.7 Hz, 1H), 8.33 (dd, J = 8.8, 1.9 Hz, 1H), 7.91 (s, 1 H), 3.89 (q, J = 7.4 Hz, 2H), 2.50 - 2.41 (m, 1H), 1.35 - 1.29 (m, 2H), 1.26 (t, J = 7.4 Hz, 3H), 1.09 - 1.00 (m, 2H), 0.30 (s, 9H). LC-MS: mass calculated for C23H23F3N2OsS2Si [M]+ 556.07, found: 557.3 (M+1).

[0815] Step-2: Manufacture of 2-(3-ethylsulfonyl-5-ethynyl-2-pyridyl)-5-(trifluoromethylsulfinyl)- 1 ,3-benzoxazole (1.38)

[0816] To a stirred solution of 2-[3-cyclopropyl-5-ethylsulfonyl-6-[5-(trifluoromethylsulfonyl)-1,3- benzoxazol-2-yl]-2-pyridyl]ethynyl-trimethyl-silane (0.05 g, 0.09 mmol) in methanol (3.0 mL) at RT was added potassium carbonate (0.001g, 0.01 mmol), reaction mixture was stirred at RT for 10 mins. The progress of the reaction was monitored by TLC which showed complete conversion after 10 mins at RT. The reaction mixture was diluted with water (20 mL) and was extracted with ethyl acetate (30 mL X 2). The combined organic layer was washed with brine solution then dried over Na2SO4 and concentrated under reduced pressure to get the crude product which was purified by flash column chromatography using 40% EtOAc in n-Heptane as an eluent to afford desired product as white solid (0.03 g, 67.27% yield).1H NMR (300 MHz, DMSO-d6) 5 8.82 (d, J = 1.8 Hz, 1H), 8.40 (dd, J = 8.7, 0.7 Hz, 1H), 8.33 (dd, J = 8.8, 1.9 Hz, 1 H), 7.91 (s, 1 H), 5.08 (s, 1 H), 3.90 (q, J = 7.4 Hz, 2H), 2.50 - 2.48 (m, 1H), 1.36 - 1.30 (m, 2H), 1.29 (t, J = 7.4 Hz, 3H), 1.10 - 0.99 (m, 2H). LC-MS: mass calculated for C20H15F3N2O5S2 [M]+ 484.03, found: 485.1 (M+1).

[0817] With appropriate modification of the starting materials or intermediates thereof, the procedures as described in the preparation example above were used to obtain further compounds of formula I listed in Table B with their physical data. Table B

[0818]

[0819]

[0820]

[0821]

[0822]

[0823]

[0824]

[0825]

[0826]

[0827]

[0828]

[0829]

[0830]

[0831]

[0832] The wavy / dotted line denotes the bond to the remainder of the molecule cyPr: cyclopropyl, Et: ethyl; Me: methyl

[0833] BASF SE 240867W001

[0834] B19464WO

[0835] 102

[0836] B. Biological Examples

[0837] The activity of the compounds of formula (I) of the invention could be demonstrated and evaluated in biological tests described in the following. If not otherwise specified, the test solutions are prepared as follows: The active compound is dissolved at the desired concentration in a mixture of 1 :1 (vokvol) distilled water : acteone. The test solution is prepared at the day of use. Test solutions are prepared in general at concentrations of 2500ppm, 800ppm, and 300ppm (wt / vol).

[0838] B.1 Boll weevil (Anthonomus grandis)

[0839] For evaluating control of boll weevil (Anthonomus grandis) the test unit consisted of 96-well- microtiter plates containing an insect diet and 5-10 A. grandis eggs. The compounds were formulated using a solution containing 75% v / v water and 25% v / v DMSO. Different concentrations of formulated compounds were sprayed onto the insect diet at 5 pl, using a custom-built micro atomizer, at two replications. After application, microtiter plates were incubated at about 25 + 1°C and about 75 + 5 % relative humidity for 5 days. Egg and larval mortality was then visually assessed. In this test, compounds 1.1 , 1.2, 1.3, 1.4, 1.5, 1.6, 1.7, 1.8,

[0840] 1.10, 1.11 , 1.12, 1.13, 1.15, 1.17, 1.18, I.20, 1.19, 1.21 , I.22, I.23, I.25, I.26, I.27, I.28, I.29, 1.30, 1.31 ,

[0841] I.33, I.34, I.35, I.36, I.38, I.39, I.40, 1.41 , I.42, I.43, I.44, I.45, I.46, I.47, I.48, I.49, 1.50, 1.51 , I.52,

[0842] I.54, I.55, I.56, I.57, I.58, I.59, I.60, 1.61 , I.62, I.63, I.64, I.65, I.66, I.67, I.68, I.69, 1.70 resp., at

[0843] 800 ppm showed over 75% mortality in comparison with untreated controls.

[0844] B.2 Tobacco budworm (Heliothis virescens)

[0845] For evaluating control of tobacco budworm (Heliothis virescens) the test unit consisted of 96- well-microtiter plates containing an insect diet and 15-25 H. virescens eggs. The compounds were formulated using a solution containing 75% v / v water and 25% v / v DMSO. Different concentrations of formulated compounds were sprayed onto the insect diet at 10 pl, using a custom-built micro atomizer, at two replications. After application, microtiter plates were incubated at about 28 + 1°C and about 80 + 5 % relative humidity for 5 days. Egg and larval mortality was then visually assessed. In this test, compounds compounds 1.1 , 1.2, 1.3, 1.4, 1.5, 1.6, 1.7, I.8, 1.10, 1.12, 1.13, 1.14, 1.15, 1.16, 1.17, 1.18, 1.19, I.20, 1.21 , I.22, I.23, I.25, I.27, I.28, I.29, I.30, 1.31 , I.32, 1.33, 1.34, 1.35, 1.36, 1.38, 1.39, I.40, 1.41 , I.42, I.43, I.44, I.45, I.46, I.47, I.48, I.49,

[0846] I.50, 1.51 , I.52, I.54, I.55, I.56, I.57, I.58, I.59, I.60, 1.61 , I.62, I.63, I.64, I.66, I.67, I.68, I.69, 1.70 resp., at 800ppm showed over 75% mortality in comparison with untreated controls.

[0847] B.3 Green Peach Aphid (Myzus persicae)

[0848] For evaluating control of green peach aphid (Myzus persicae) through systemic means the test unit consisted of 96-well-microtiter plates containing liquid artificial diet under an artificial membrane. The compounds were formulated using a solution containing 75% v / v water and 25% v / v DMSO. Different concentrations of formulated compounds were pipetted into the aphid diet, using a custom built pipetter, at two replications. After application, 5 - 8 adult aphids were placed on the artificial membrane inside the microtiter plate wells. The aphids were then allowed to suck on the treated aphid diet and incubated at about 23 + 1 °C and about 50 + 5 % relative humidity for 3 days. Aphid mortality and fecundity was then visually assessed. In this test, compounds compounds 1.1 , I.2, I.4J.6, I.8, 1.10, 1.12, 1.15, 1.16, 1.17, 1.18, 1.19, I.20, 1.21 , I.23, BASF SE 240867W001

[0849] B19464WO

[0850] 103

[0851] I.25, I.27, I.28, I.29, I.30, 1.31 , 1.33, 1.34, 1.35, 1.38, 1.39, 1.41 , I.42, I.43, I.44, I.47, I.48, I.49, 1.51 , I.52, I.54, I.55, 1.56, 1.57, 1.58, 1.59, I.60, 1.61 , I.62, I.63, I.64, I.65, I.66, I.67, I.68, I.69, 1.70 resp., at 800 ppm showed over 75 % mortality in comparison with untreated controls.

[0852] B.4 Diamond back moth (Plutella xylostella)

[0853] The active compound is dissolved at the desired concentration in a mixture of 1 :1 (vokvol) distilled water: acetone. Surfactant (Kinetic) is added at a rate of 0.01 % (vol / vol).The test solution is prepared at the day of use. Cabbage leaf discs (60mm in diameter) are dipped in test solution and air-dried. Treated leaves are placed in petri dishes lined with moistened filter paper and inoculated with ten 3rdinstar larvae. Mortality is recorded 72 hours after treatment. Feeding damage is also recorded using a scale of 0-100%. In this test, compounds compounds 1.1 , 1.2, 1.3, I.4, I.6, 1.7, 1.8, 1.9, 1.10, 1.11 , 1.12, 1.13, 1.14, 1.15, 1.16, 1.17, 1.18, 1.19, I.20, 1.21 , I.22, I.23, I.24, I.25, I.26, I.27, I.28, I.30, 1.31 , 1.33, 1.34, 1.35, 1.36, 1.37, 1.38, 1.39, I.40, I.42, I.43, I.44, I.45, I.46, I.47, I.48, I.49, I.50, 1.51 , I.52, I.54, 1.55, 1.56, 1.57, 1.58, 1.59, I.60, 1.61 , I.62, I.63, I.64, I.65,

[0854] 1.66, 1.67, 1.68, 1.69, 1.70 respectively, at 800 ppm showed over 75% mortality in comparison with untreated controls.

[0855] B.5 Southern armyworm (Spodoptera eridania), 2nd instar larvae

[0856] The active compounds were formulated by a Tecan liquid handler in 100% cyclohexanone as a 10,000 ppm solution supplied in tubes. The 10,000 ppm solution was serially diluted in 100% cyclohexanone to make interim solutions. These served as stock solutions for which final dilutions were made by the Tecan in 50% acetone:50% water (v / v) into 10 or 20ml glass vials. A nonionic surfactant (Kinetic®) was included in the solution at a volume of 0.01% (v / v). The vials were then inserted into an automated electrostatic sprayer equipped with an atomizing nozzle for application to plants / insects. Lima bean plants (variety Sieva) were grown 2 plants to a pot and selected for treatment at the 1sttrue leaf stage. Test solutions were sprayed onto the foliage by an automated electrostatic plant sprayer equipped with an atomizing spray nozzle. The plants were dried in the sprayer fume hood and then removed from the sprayer. Each pot was placed into perforated plastic bags with a zip closure. Ten to 11 armyworm larvae were placed into the bag and the bags zipped closed. Test plants were maintained in a growth room at about 25°C and about 20-40% relative humidity for 4 days, avoiding direct exposure to fluorescent light (14:10 light:dark photoperiod) to prevent trapping of heat inside the bags. Mortality and reduced feeding were assessed 4 days after treatment, compared to untreated control plants. In this test, compounds compounds 1.1 , 1.3, I.5, I.6, 1.7, 1.8, 1.12, 1.13, 1.15, 1.17, 1.18, 1.19, I.20, 1.21 , I.22, I.23, I.24, I.25, I.27, I.28, I.29, 1.30, 1.31 , 1.32, 1.33, 1.34, 1.35, 1.36, 1.39, I.40, 1.41 , I.42, I.43, I.44, I.45, I.46, I.47, I.48, I.49, 1.50, 1.51 , 1.52, 1.54, I.56, I.57, 1.58, 1.59, I.60, 1.61 , I.63, I.64, I.66,

[0857] 1.67, 1.68, 1.69, 1.70 respectively, at 100 ppm showed over 75% mortality in comparison with untreated controls.

[0858] B.6 Yellow fever mosquito (Aedes aegypti)

[0859] For evaluating control of yellow fever mosquito (Aedes aegypti) the test unit consisted of 96- well-microtiter plates containing 200 pl of tap water per well and 5-15 freshly hatched A. aegypti larvae. The active compounds were formulated using a solution containing 75% (v / v) water and 25% (v / v) DMSO. Different concentrations of formulated compounds or mixtures were sprayed BASF SE 240867W001

[0860] B19464WO

[0861] 104 onto the insect diet at 2.5pl , using a custom built micro atomizer, at two replications. After application, microtiter plates were incubated at 28 + 1 °C, 80 + 5 % RH for 2 days. Larval mortality was then visually assessed. In this test, compounds 1.1 , 1.2, 1.3, 1.4, 1.5, 1.6, 1.7, 1.8,

[0862] 1.10, 1.11 , 1.12, 1.13, 1.14, 1.15, 1.16, 1.17, 1.18, 1.19, I.20, 1.21 , I.22, I.23, I.25, I.27, I.28, I.29, 1.30,

[0863] 1.31 , I.33, I.34, 1.35, 1.36, 1.39, I.40, 1.41 , I.42, I.43, I.44, I.45, I.47, I.48, I.49, 1.50, 1.51 , I.52, 1.54,

[0864] 1.55, 1.56, 1.57, 1.58, I.59, I.60, 1.61 , I.63, I.64, I.65, I.66, I.67, I.68, I.69, 1.70 at 800 ppm showed at least 75 % mortality in comparison with untreated controls.

[0865] B.7 Chilo suppressalis (Striped Stem Borer)

[0866] The active compound was dissolved at the desired concentration in a mixture of 1 :1 (vokvol) distilled water : acetone. Surfactant (Kinetic) was added at a rate of 0.01% (vol / vol). The test solution was prepared at the day of use.

[0867] Each block of sliced artificial diet (1 x 1 x 1 cm) was dipped into plastic weigh boats with about 2 ml test solution. After dipping, treated diet blocks were individually placed in plastic containers for air-drying, which were then inoculated with 10 neonates (L1) of striped stemborer using fine camel’s hair brush. Set-up was kept in a holding room maintained at 26 - 27°C and 50 - 70% relative humidity. Assessment was done by counting the number of dead and alive larvae three and five days after treatment application.

[0868] In this test, compounds 1.1 , 1.3, I.6, 1.7, 1.8, 1.12, 1.13, 1.15, 1.17, 1.18, 1.19, I.20, 1.21 , I.22, I.24, I.27, 1.30, 1.31 , 1.35, 1.36, I.39, I40, 1.41 , I.42, I.46, I.47, I.48, I.54, I.56, I.57, 1.58, 1.59, I.60, 1.61 , 1.67, 1.69 at 100 ppm showed over 75 % mortality in comparison with untreated controls.

[0869] B.8 Laphygma fruiperda (Fall Armyworm)

[0870] The active compound was dissolved at the desired concentration in a mixture of 1:1 (vol: vol) distilled water: acetone. Surfactant (Kinetic) was added at a rate of 0.01% (vol / vol). The test solution was prepared at the day of use.

[0871] Each plastic cup with block of artificial diet (1 x 1 x 1 cm) was sprayed with 0. 125 ml test solution using the Tamiya make-up sprayer at 0.2 MPa under the laboratory hood. After airdrying, each plastic container was inoculated with 10 neonates (L1) of fall armyworm using fine camel’s hair paint brush. Set-up was kept in a holding room maintained at 25 - 27°C and 50 - 70% relative humidity. Assessment was done by counting the number of dead and alive larvae at 120 hours after treatment. In this test, compounds 1.3, 1.6, 1.7, 1.8, 1.12, 1.13, 1.15, 1.17, 1.19, 1.21 , I.22, I.24, I.27, 1.35, I.36, 1.39, I40, I.42, I.47, I.48, I.54, I.56, I.57, I.58, I.59, I.60, 1.61 , I.67, 1.69 at 100 ppm showed over 75 % mortality in comparison with untreated controls.

[0872] C. Comparative Examples

[0873] For evaluating the activity of the compounds relative to structurally similar compounds of the prior art, biological tests were carried out as described above. The results are shown in Tables C to F below. The compounds of the invention showed higher activities in all biological tests compared to the prior art compounds.

[0874] Compounds C32 and C45 as described in EP 3018130 A1 were synthesized and tested for biological activity. Compounds 1.47 and 1.59 according to the present invention were tested BASF SE 240867W001

[0875] B19464WO

[0876] 105 under the same conditions. The results are shown in table C to E, wherein the test species are Chilo suppressalis (Rice stemborer) and Laphygma fruiperda (Fall armyworm).

[0877] Table C

[0878] Table C - Test species: Chilo suppressalis (test B.7)

[0879] Table D - test species: Laphygma fruiperda (test B.8)

[0880] Table E - test species: Chilo suppressalis (test B.7)

[0881] Compound X that falls under the scope of US 2023 / 212163 A1 , is a compound of the following and was synthesized and tested for biological activity. Compound 1.64 according to the present invention was tested under the same conditions. The results are shown in table F, wherein the test species is Aedes aegypti (Yellow fever mosquito). BASF SE 240867W001

[0882] B19464WO

[0883] 106

[0884] Table F - test species: Aedes aegypti (test B.6)

Claims

BASF SE 240867W001B19464WO107Claims1 . A compound of formula (I)whereinR1is S(O)m-Ci-C4-alkyl, S(O)m-C3-C6-cycloalkyl, S(O)m-C3-C6-cycloalkyl-Ci-C4-alkyl, which are unsubstituted or halogenated; S(O)(=NH)RM, S(O)(=NRM)RM;Ci-C4-alkyl, Cs-Ce-cycloalkyl, Ci-C4-alkoxy, -O-Cs-Ce-cycloalkyl, all of which are unsubstituted, partially halogenated or fully halogenated;Rwis Ci-C4-alkyl, cyclopropyl, C3-C6-cycloalkyl-Ci-C4-alkyl; m is 0, 1 or 2; n is 0, 1 or 2;R2is Ci-C4-alkyl, Ci-C4-alkoxy, Cs-Ce-cycloalkyl, halogen, cyano, NHRM, N(RM)2, NH-CO- RM, CO-NH2, CO-NHRM, CO-N(RM)2;Ci-C4-alkynyl; or phenyl which is unsubstituted or substituted with at least one Ci-C4-alkyl which is unsubstituted or partially or fully halogenated; Cs-Ce-cycloalkyl, halogen, O-S(O)2-RM, CN, Ci-Cs-alkoxy, which is unsubstituted or partially or fully halogenated, C3-C6- cycloalkoxy; N=S(O)(RM)2 or a five- or six-membered heterocycle, which is saturated, partially unsaturated or fully unsaturated, and which is unsubstituted or substituted with at least one halogen, CN, Ci-C4-alkyl which is unsubstituted or partially or fully halogenated; Cs-Ce-cycloalkyl, C1- Cs-alkoxy, which is unsubstituted or partially or fully halogenated;R3is(1) Cs-Ce-cycloalkyl, which is unsubstituted or partially or fully halogenated; or halogen;(2) phenyl substituted with (a) one R4, or (b) substituted with one R4and one halogen, or (c) substituted with up to 5 halogens;(3) 1 ,3-benzodioxole which is unsubstituted or partly or fully halogenated;(4) a six-membered saturated, partially unsaturated, or fully unsaturated heterocyclic ring or ring system, wherein said heterocyclic ring or ring system comprises one, two or three, same or different heteroatoms O or N which may be unsubstituted or substituted with Ci-C4-alkyl, and is unsubstituted, or substituted with one R4, or substituted with two halogens;(5) or Ci-C4-alkynyl, which is unsubstituted or substituted with Cs-Ce-cycloalkyl or Si(R5)3; wherein R5is Ci-C4-alkyl; or(6) a five-membered saturated, partially unsaturated, or fully unsaturated heterocyclic ring, wherein said heterocyclic ring comprises one, two or three, same or different heteroatoms selected from N, O, and S, wherein N may be unsubstituted or substitutedBASF SE 240867W001B19464WO108 with Ci-C4-alkyl, Cs-Ce-cycloalkyl, C-bound Ci-C4-alkoxy, Ci-C4-alkyl-Ci-C4-alkoxy; wherein the five-membered ring is unsubstituted or substituted with one R4,R4is halogen, cyano, Ci-C4-alkyl, which is unsubstituted or partially or fully halogenated; NH-CO-RM; Cs-Ce-cycloalkyl;Ci-C4-alkoxy-Ci-C4-alkyl, Cs-Ce-cycloalkyl-Ci-Cs-alkoxy, Ci-C4-alkoxy-Ci-C4-alkoxy-Ci- C4-alkyl;C(RM)2-CN, CHRM-CN, C(RM)2-(CONH2), CHRM-(CONH2), C(RM)2-(CSNH2), CHRM- (CSNH2), l-cyano-Cs-Ce-cycloalkyl, 1-Cs-Ce-cycloalkyl-carboxamide, 1-Cs-Ce- cycloalkyl-thiocarboxamide, O-CH2-CN, O-CHRM-CN, O-C(RM)2-CN, O-C(RM)2-(CONH2), O-C(RM)2-(CSNH2), O-l-cyano-Cs-Ce-cycloalkyl, O-C(CONH2)-C3-C6-cycloalkyl, O-C(CSNH2)-Cs-Ce- cycloalkyl; O-S(O)2-RM;Ci-Cs-alkoxy, which is unsubstituted or partially or fully halogenated; Cs-Ce-cycloalkyl- Ci-Cs-alkoxy which is unsubstituted or partially or fully halogenated, Cs-Ce-cycloalkoxy, which is unsubstituted or partially or fully halogenated; S-RM, SO-RM; SO2-RM;S(O)(=NRM)RM, S(O)(=NH)RM, N=S(O)(RM)2, CO-N=SO(RM)2, SF5, (=O), C(=O)H, C(=O)RM, difluoromethylen, each RMis independently Ci-Cs-alkyl which is unsubstituted or partially or fully halogenated; or Cs-Ce-cycloalkyl, or Cs-Ce-cycloalkyl in which at least one C is replaced by a heteroatom; or in case of two adjacent substituents RM, the substituents may form a ring together by a C2-Ce-alkyl bridge, which is unsubstituted or partly or fully halogenated and in which one or more carbon atoms may be replaced by O or N; and the N-oxides, stereoisomers, tautomers and agriculturally or veterinarily acceptable salts thereof.

2. The compound of formula (I) according to claim 1 , whereinR1is S(O)m-Ci-C4-alkyl, S(O)m-Cs-C6-cycloalkyl, S(O)m-Cs-C6-cycloalkyl-Ci-C4-alkyl, which are unsubstituted or halogenated; S(O)(=NH)RM, S(O)(=NRM)RM; preferably whereinR1is (S=O)-CF3, SO2-CF3, SCF3, S(O)(=NH)CF3or S(O)(=NCH3)CF3, and Rwis ethyl, n is 2.

3. The compound of formula (I) according to claim 1 or 2, in whichR2is Ci-C4-alkyl, Ci-C4-alkoxy, Cs-Ce-cycloalkyl, halogen, cyano, N(RM)2, NH-CO-RM; Ci-C4-alkynyl;Preferably wherein R2is methyl, cyclopropyl, chloro, cyano, Preferably wherein R2is methyl.

4. The compound of formula (I) according to any of claims 1 to 3, in which R3is Cs-Ce-cycloalkyl, preferably cyclopropyl; or R3is bromo.BASF SE 240867W001B19464WO1095. The compound of formula (I) according to any of claims 1 to 3, in whichR3is phenyl substituted with one R4, or substituted with up to 5 halogens; or 1 ,3-benzodioxole which is unsubstituted or partly or fully halogenated;PreferablyR3is phenyl substituted with one R4, or substituted with 2 halogens.

6. The compound of formula (I) according to any of claims 1 to 3, in whichR3is a six-membered saturated, partially unsaturated, or fully unsaturated heterocyclic ring or ring system, wherein said heterocyclic ring or ring system comprises one, two or three, same or different heteroatoms O or N which may be unsubstituted or substituted with Ci-C4-alkyl, and is unsubstituted, or substituted with one R4, or substituted with two halogens.

7. The compound of formula (I) according to any of claims 1 to 3, in whichR3is a five-membered saturated, partially unsaturated, or fully unsaturated heterocyclic ring, wherein said heterocyclic ring comprises one, two or three, same or different heteroatoms selected from N, O, and S, wherein N may be unsubstituted or substituted with Ci-C4-alkyl, Cs-Ce-cycloalkyl, C-bound Ci-C4-alkoxy, Ci-C4-alkyl-Ci-C4-alkoxy; wherein the five-membered ring is unsubstituted or substituted with one R4;Preferably wherein R3is pyridyl substituted with one R4.

8. The compound of formula (I) according to claim 7, in which R3is one of the following heterocycles R3.5.1 to R3.5.15:preferably wherein R3is R3.5.1 or R3.5.5.

9. The compound of formula (I) according to any of claims 1 to 8, in whichR4is halogen, cyano, NH-CO-RM;C(RM)2-CN, l-cyano-Cs-Ce-cycloalkyl, l-Cs-Ce-cycloalkyl-carboxamide, I-C3-C6- cycloalkyl-thiocarboxamide,O-C(RM)2-(CONH2),BASF SE 240867W001B19464WO110O-S(O)2-RM;Ci-Cs-alkoxy, which is unsubstituted or partially or fully halogenated; C3-C6- cycloalkoxy, which is unsubstituted or partially or fully halogenated;SO-RM; N=S(O)(RM)2, CO-N=SO(RM)2.

10. The compound of formula (I) according to any of claims 1 to 9, in which each RMis independently Ci-Cs-alkyl which is unsubstituted or partially or fully halogenated; preferably methyl or trifluoromethyl.

11. A composition comprising the compound of formula (I), as defined in any of claims 1 to 10, an N-oxide or an agriculturally acceptable salt thereof and at least one inert liquid and / or solid carrier.

12. A method for combating or controlling invertebrate pests, which method comprises contacting said pest or its food supply, habitat or breeding grounds with a pesticidally effective amount of at least one compound of the formula (I) according to any of claims 1 to 10 or the composition according to claim 11 .

13. A method for protecting growing plants from attack or infestation by invertebrate pests, which method comprises contacting a plant, or soil or water in which the plant is growing, with a pesticidally effective amount of at least one compound of the formula (I), according to any of the claims claims 1 to 10 or the composition according to claim 11 .

14. Seed comprising a compound of the formula (I), as defined in any of claims 1 to 10, or the composition as defined in claim 11 , in an amount of from 0.1 g to 10 kg per 100 kg of seed.

15. A method for protection of plant propagation material comprising contacting the plant propagation material with the pesticidal compound of formula (I) as defined in any of claims 1 to 10 in an amount of from 0.1 g to 10 kg per 100 kg of plant propagation material.

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