Pesticidally active cyclic amine compounds

Abstract

Compounds of formula (I) wherein the substituents are as defined in claim 1 and the agrochemically acceptable salts, stereoisomers, enantiomers, tautomers and N-oxides of those compounds can be used as insecticides and acaricides. # imgabs0 #

Description

[0001] The present invention relates to piperidinyl-pyridylcarbonyl compounds having pesticidal activity (especially insecticidal activity), processes for their preparation, compositions comprising those compounds, and their use for controlling animal pests, including arthropods and especially representatives of the order Insecta or Acarina.

[0002] WO 2017195703, WO 2019039429, WO 2019082808, JP 2019085371, WO2021053161, WO 2021160680, WO 2021215393 and WO 2022219146 describe certain piperidinyl-pyridylcarbonyl compounds for controlling pests damaging plants.

[0003] Now novel pesticidal piperidinyl-pyridylcarbonyl compounds have been found.

[0004] Accordingly, in a first aspect, the present invention relates to compounds of formula (I)

[0005]

[0006] wherein

[0007] R 1 is CN or C(=S)NH2;

[0008] R 2 is H or methyl;

[0009] R 3 is C1-C2-alkyl, C1-C2-haloalkyl, C3-C6-cycloalkyl, C1-C2-alkoxy-C1-C2-alkyl;

[0010] R 4 is independently selected from halogen, C1-C2-haloalkyl, C1-C2-haloalkoxy, -O-C 1-2 haloalkanediyl-O-;

[0011] q is 1, 2 or 3; or

[0012] or an agronomically acceptable salt, enantiomer, tautomer and / or N-oxide of the compound of formula I.

[0013] Compounds of formula (I) having at least one basic center can form, for example, acid addition salts with, for example: strong inorganic acids (such as mineral acids, for example perchloric acid, sulfuric acid, nitric acid, nitrous acid, phosphoric acid or hydrohalic acids), strong organic carboxylic acids (such as unsubstituted or, for example, halogen-substituted C1-C4 alkanoic acids, for example acetic acid, such as saturated or unsaturated dicarboxylic acids, for example oxalic acid, malonic acid, succinic acid, maleic acid, fumaric acid or phthalic acid, such as hydroxycarboxylic acids, for example ascorbic acid, lactic acid, malic acid, tartaric acid or citric acid, or such as benzoic acid), or organic sulfonic acids (such as unsubstituted or, for example, halogen-substituted C1-C4 alkanesulfonic acids or arylsulfonic acids, for example methanesulfonic acid or p-toluenesulfonic acid). Compounds of formula (I) having at least one acidic group can form salts, for example, with bases, such as mineral salts, for example alkali metal or alkaline earth metal salts, for example sodium salts, potassium salts or magnesium salts; or with ammonia or organic amines (such as morpholine, piperidine, pyrrolidine, mono-, di- or tri-lower alkylamines, for example ethylamine, diethylamine, triethylamine or dimethylpropylamine, or mono-, di- or tri-hydroxy-lower alkylamines, for example monoethanolamine, diethanolamine or triethanolamine).

[0014] In each case, the compounds of formula (I) according to the invention are in free form, in oxidized form (such as N-oxides) or in salt form (for example in the form of agrochemically useful salts).

[0015] N-oxides are the oxidized forms of tertiary amines or of nitrogen-containing heteroaromatic compounds. They are described, for example, in the book “Heterocyclic N-oxides” by A. Albini and S. Pietra, CRC Press, Boca Raton 1991.

[0016] The compounds of formula (I) according to the invention also include the hydrates that may form during salt formation.

[0017] As used herein, the term “C1-C n -alkyl” refers to saturated alkyls, for example any one of the groups methyl and ethyl.

[0018] As used herein, the term “C3-C n -cycloalkyl” refers to 3-membered - n-membered cycloalkyls, such as cyclopropane and cyclobutane.

[0019] As used herein, the term “C1-C n -alkoxy” refers to straight-chain or branched-chain saturated alkyls having 1 to n carbon atoms (as mentioned above), which are attached via an oxygen atom, i.e., for example any one of the groups methoxy and ethoxy. As used herein, the term “halo C1-C n -alkoxy” refers to C1-Cn -alkoxy, wherein one or more hydrogen atoms on the alkyl group are replaced by one or more identical or different halogen atoms - examples include trifluoromethoxy, difluoromethoxy, fluoromethoxy or 2-fluoroethoxy. Two adjacent substituents on the phenyl ring may together with the carbon of the phenyl ring form a 5- or 6-membered ring. Examples are -OCF2O- and -OCF2CF2O-.

[0020] Halogen is generally fluorine, chlorine, bromine or iodine. This also correspondingly applies to halogen in combination with other meanings, such as haloalkyl.

[0021] As used herein, the term "C1-C n -haloalkyl" means a straight-chain saturated alkyl group having 1 to n carbon atoms attached via any carbon atom (as mentioned above), wherein some or all of the hydrogen atoms in these groups may be replaced by fluorine, chlorine, bromine and / or iodine, i.e., for example, any of the following: chloromethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 2-fluoroethyl, 2-chloroethyl, 2-bromoethyl, 2-iodoethyl, 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 or pentafluoroethyl. Correspondingly, the term "C1-C2 fluoroalkyl" will mean a C1-C2 alkyl group bearing 1, 2, 3, 4 or 5 fluorine atoms, such as any of the following: difluoromethyl, trifluoromethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 1,1,2,2-tetrafluoroethyl or pentafluoroethyl.

[0022] As used herein, the term "C1-C n -alkoxy-C1-C n -alkyl" means an alkyl group substituted by C1-C n -alkoxy. Examples are methoxymethyl, methoxyethyl and ethoxymethyl.

[0023] As used herein, the term "-O-C 1-2 haloalkanediyl-O-" means adjacent positions on a benzene ring that are connected to the oxygen atom of the -O-C 1-2 haloalkanediyl-O- group and the oxygen atom is connected by 1 to 2 carbon atoms substituted by one or more halogen atoms. Examples are -OCF2O- and -OCF2CF2O-.

[0024] As used herein, the term "control" means reducing the number of pests, eliminating pests and / or preventing further pest damage, such that damage to the plant or to plant-derived products is reduced.

[0025] As used herein, the term "pest" refers to insects and mollusks present in the storage of agricultural, horticultural, forestry, and plant-derived products (such as fruits, grains, and wood); and those pests related to the damage of man-made structures. The term pest encompasses all stages of the life cycle of said pests.

[0026] As used herein, the term "effective amount" refers to the amount of a compound or its salt that provides the desired effect upon single or multiple applications.

[0027] The effective amount can be readily determined by those skilled in the art using known techniques and by observing the results obtained in similar situations. In determining the effective amount, many factors are considered, including but not limited to: the type of plant or derivative product to be applied; the pest to be controlled and its life cycle; the specific compound being applied; the type of application; and other relevant circumstances.

[0028] Embodiments according to the present invention are provided as listed below.

[0029] In embodiments of each aspect of the present invention, R 1 is

[0030] A. C(=S)NH2; or

[0031] B. CN.

[0032] In embodiments of each aspect of the present invention, R 2 is

[0033] A. hydrogen; or

[0034] B. methyl.

[0035] In embodiments of each aspect of the present invention, R 3 is

[0036] A. C1-C2-alkyl, C1-C2-haloalkyl, C3-C4-cycloalkyl, or C1-C2-alkoxy-C1-C2-alkyl; or

[0037] B. methyl, ethyl, cyclopropyl, monofluoromethyl, difluoromethyl, trifluoromethyl, methoxymethyl, or ethoxymethyl; or

[0038] C. methyl, ethyl, cyclopropyl, monofluoromethyl, difluoromethyl, trifluoromethyl, or methoxymethyl; or

[0039] D. methyl, difluoromethyl, trifluoromethyl, or methoxymethyl; or

[0040] E. methyl, trifluoromethyl, or methoxymethyl.

[0041] In embodiments of each aspect of the present invention, R 4 is independently selected from

[0042] A. fluorine, bromine, chlorine, iodine, trifluoroethyl, trifluoromethyl, difluoromethyl, trifluoromethoxy, difluoromethoxy, -OCF2O- and -OCF2CF2O-; or

[0043] B. fluorine, chlorine, bromine, trifluoromethyl, difluoromethyl, difluoromethoxy, trifluoromethoxy, and -OCF2O-; or

[0044] C. fluorine, trifluoromethyl, trifluoromethoxy, and -OCF2O-; or

[0045] D. trifluoromethyl and -OCF2O-.

[0046] In embodiments of each aspect of the present invention, q (with respect to halogen, C1-C2-haloalkyl, and C1-C2-haloalkoxy) is

[0047] A. 1, 2 or 3; or

[0048] B. 1 and 2; or

[0049] C. 1.

[0050] Thus, the present invention enables the obtaining of compounds of formula I having substituents R in all combinations / each permutation as defined above 1 , R 2 , R 3 and R 4 . Thus, it is possible to obtain, for example, a compound of formula I where R 1 is embodiment B (i.e., CN); R 2 is embodiment A (i.e., R 2 is hydrogen); R 3 is embodiment B (i.e., R 3 is methyl, ethyl, cyclopropyl, monofluoromethyl, difluoromethyl, trifluoromethyl, methoxymethyl, or ethoxymethyl); and R 4 is embodiment B (i.e., selected from fluorine, chlorine, bromine, trifluoromethyl, difluoromethyl, difluoromethoxy, trifluoromethoxy, and -OCF2O-; where q (with respect to fluorine, chlorine, bromine, trifluoromethyl, difluoromethyl, and trifluoromethoxy) is embodiment B (i.e., 1 or 2)).

[0051] In embodiments of each aspect of the present invention, the compound of formula I has a cyano group or C(=S)NH2 as R 1 ; hydrogen or methyl as R 2 ; as R 3a C1-C2-alkyl, C1-C2-haloalkyl, C3-C4-cycloalkyl, or C1-C2-alkoxy-C1-C2-alkyl; and as R 4 independently selected from one or two substituents from halogen, C1-C2-haloalkyl, and C1-C2-haloalkoxy, or -OCF2O-.

[0052] In an embodiment of each aspect of the present invention, the compound having formula I has as R 1 a cyano or C(=S)NH2; as R 2 hydrogen or methyl; as R 3 methyl, ethyl, cyclopropyl, monofluoromethyl, difluoromethyl, trifluoromethyl, or methoxymethyl; and as R 4 independently selected from one or two substituents from fluorine, bromine, chlorine, difluoromethyl, trifluoromethyl, difluoromethoxy, and trifluoromethoxy, or -OCF2O-.

[0053] In an embodiment of each aspect of the present invention, the compound having formula I has as R 1 a cyano; as R 2 hydrogen or methyl; as R 3 methyl, difluoromethyl, trifluoromethyl, or methoxymethyl; as R 4 4-trifluoromethyl, or 3-OCF2O-4.

[0054] In an embodiment of each aspect of the present invention, the compound having formula I has as R 1 a cyano; as R 2 methyl; as R 3 methyl, trifluoromethyl, or methoxymethyl; as R 4 4-trifluoromethyl, or 3-OCF2O-4.

[0055] In a second aspect, the present invention makes it possible to obtain a composition comprising a compound having formula (I) as defined in the first aspect, one or more auxiliaries and diluents, and optionally one or more other active ingredients.

[0056] In a third aspect, the present invention makes it possible to obtain a method for combating and controlling insects, mites, nematodes or molluscs, the method comprising applying to the pest, the locus of the pest, or a plant susceptible to attack by the pest an insecticidally, acaricidally, nematicidally or molluscicidally effective amount of a compound as defined in the first aspect or a composition as defined in the second aspect.

[0057] In a fourth aspect, the present invention makes it possible to obtain a method for protecting plant propagation material against attack by insects, mites, nematodes or molluscs, which method comprises treating the propagation material or the site on which the propagation material is grown with an effective amount of a compound of formula (I) as defined in the first aspect or a composition as defined in the second aspect.

[0058] In a fifth aspect, the present invention makes it possible to obtain a plant propagation material, such as a seed, which plant propagation material comprises a compound of formula (I) as defined in the first aspect or a composition as defined in the second aspect, or is treated with the compound or the composition, or has the compound or the composition attached thereto.

[0059] In another aspect, the present invention provides a method for controlling parasites in or on an animal in need thereof, said method comprising administering an effective amount of the compound of the first aspect. The present invention further provides a method for controlling ectoparasites of an animal in need thereof, which method comprises administering an effective amount of a compound of formula (I) as defined in the first aspect. The present invention further provides a method for preventing and / or treating a disease transmitted by ectoparasites, which method comprises administering an effective amount of a compound of formula (I) as defined in the first aspect to an animal in need thereof.

[0060] The compounds of formula (I) can be prepared by those skilled in the art according to known methods. More specifically, the compounds of formula I and their intermediates can be prepared as described below in the schemes and examples.

[0061] The method for preparing the compounds of formula (I) according to the present invention is carried out by methods known to those skilled in the art.

[0062] The compounds of formula (I) in which R 1 , R 2 , R 3 , R 4 and q) are new and can be prepared according to Scheme 1 by reacting an acid II (wherein R 1 , R 3 , R 4 and q are as previously defined) with an amine III (wherein R 2 is as previously defined) or a salt thereof using a known amide coupling reagent such as 1-[bis(dimethylamino)-methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxide hexafluorophosphate (HATU) and a base such as Hünig's base in a suitable solvent (such as dimethylformamide (DMF) or dimethylacetamide (DMA)). Piperidine III is commercially available or can be prepared by those skilled in the art.

[0063] Scheme 1:

[0064]

[0065] Alternatively, the compound of formula (I) can be prepared according to Scheme 2 by reacting an acyl chloride IV (wherein R 1 , R 3 , R 4 and q are as defined previously) with an amine III (wherein R 2 is as defined previously) or a salt thereof in the presence of a base (such as triethylamine or pyridine) and a suitable solvent (such as dichloromethane (DCM), tetrahydrofuran (THF) or toluene).

[0066] Scheme 2:

[0067]

[0068] The acyl chloride IV (wherein R 1 , R 3 , R 4 and q are as defined previously) can be prepared according to Scheme 3 by treating the corresponding acid II (wherein R 1 , R 3 , R 4 and q are as defined previously) with oxalyl chloride or thionyl chloride in an inert solvent (such as DCM or THF) in the presence of a catalytic amount of DMF at a temperature between 20 °C and 100 °C (preferably 25 °C).

[0069] Scheme 3:

[0070]

[0071] The acid II (wherein R 1 , R 3 , R 4 and q are as defined previously) can be prepared according to Scheme 4 by hydrolyzing the corresponding ester V (wherein R 1 , R 3 , R 4 and q are as defined previously and R x = C1-C6-alkyl) under basic conditions using an inorganic base (such as lithium hydroxide, sodium hydroxide, potassium hydroxide or potassium carbonate) in water, methanol, ethanol or THF.

[0072] Scheme 4:

[0073]

[0074] The ester V (wherein R 1 , R3 and R 4 and R x and q (as previously defined) can be prepared by palladium-catalyzed cross-coupling reaction of compound VI (wherein R 1 and R 3 and R x are as previously defined and LG 1 is a leaving group such as bromine, chlorine or sulfonate such as trifluoromethanesulfonate) with boric acid VII or stannane reagent VIII (wherein R 4 and q are as previously defined). Palladium-catalyzed cross-coupling reactions are known to those skilled in the art. These reactions according to Scheme 5 can be carried out in various organic or aqueous solvents compatible with these conditions, at a temperature from below 0 °C to the boiling point of the solvent system and with various palladium catalysts such as tetrakis(triphenylphosphine)palladium(0) or palladium(II) acetate and triphenylphosphine.

[0075] Scheme 5:

[0076]

[0077] Ester VI (wherein for example R 1 is cyano, LG 1 is a bromine atom or a chlorine atom and R 3 and R x are as previously defined) can be prepared by reacting ester IX with a halogenating reagent (such as phosphorus oxychloride, oxalyl dichloride, or phosphorus oxybromide respectively). According to Scheme 6, this reaction can be carried out in dimethylformamide (DMF) or dichloromethane (DCM), toluene or preferably without solvent at an elevated temperature.

[0078] Ester VI (wherein for example R 1 is cyano, LG 1 is trifluoromethanesulfonate and R 3 and R x are as previously defined) can be prepared by reacting ester IX with trifluoromethanesulfonic anhydride. According to Scheme 6, this reaction can be carried out in dimethylformamide (DMF) or dichloromethane (DCM), toluene in the presence of a base (such as pyridine).

[0079] Scheme 6:

[0080]

[0081] The ester having formula IX (wherein R 1 is cyano and R 3 and R x(As defined previously) is known in the literature, for example, Y. Xie et al., Pest Manag. Sci. [Pest Management Science] 2017, 73, 945 - 952, or can be prepared by those skilled in the art.

[0082] A compound having the formula (I - b), wherein R 2 , R 3 , R 4 and q are as defined previously, can be prepared according to Scheme 7 by reacting a compound having the formula (I - a), wherein R 2 , R 3 , R 4 and q are as defined previously, with ammonium sulfide in a suitable solvent (such as a mixture of methanol and water) or with phosphorus sulfide (P2S5) in ethanol.

[0083] Scheme 7:

[0084]

[0085] The compounds having the formula (I) according to Tables 1 to 7 below can be prepared by the methods described above. The following examples are intended to illustrate the invention and show the preferred compounds having the formula (I).

[0086]

[0087] Each of Tables 1 to 7 after Table M below includes 156 compounds having the formula (I), wherein R 1 , R 2 and (R 4 ) q have the values given in each row of Table M, and R 3 has the values given in the relevant Tables 1 to 7.

[0088] Thus, Compound 1.1 corresponds to a compound having the formula (I), wherein R 1 , R 2 and (R 4 ) q are defined as in the first row of Table M and wherein R 3 is defined as in Table 1; Compound 5.14 corresponds to a compound having the formula (I), wherein R 1 , R 2 and (R 4 ) q are defined as in the fourteenth row of Table M and wherein R 3 is defined as in Table 5; and so on.

[0089] Table M:

[0090]

[0091]

[0092]

[0093]

[0094]

[0095] Table 1: This table discloses 156 compounds 1.1 to 1.156 of formula (I), wherein R 3 is methyl and R 1 , R 2 and (R 4 ) q are as defined in Table M. For example, compound No. 1.1 has the following structure:

[0096]

[0097] Table 2 : This table discloses 156 compounds 2.1 to 2.156 of formula (I), wherein R 3 is ethyl and R 1 , R 2 and (R 4 ) q are as defined in Table M.

[0098] Table 3 : This table discloses 156 compounds 3.1 to 3.156 of formula (I), wherein R 3 is cyclopropyl and R 1 , R 2 and (R 4 ) q are as defined in Table M.

[0099] Table 4 : This table discloses 156 compounds 4.1 to 4.156 of formula (I), wherein R 3 is methoxymethyl and R 1 , R 2 and (R 4 ) q are as defined in Table M.

[0100] Table 5 : This table discloses 156 compounds 5.1 to 5.156 of formula (I), wherein R 3 is fluoromethyl and R 1 , R 2 and (R 4 )q As defined in Table M.

[0101] Table 6 : This table discloses 156 compounds 6.1 to 6.156 of formula (I), wherein R 3 is difluoromethyl and R 1 , R 2 and (R 4 ) q As defined in Table M.

[0102] Table 7 : This table discloses 156 compounds 6.1 to 6.156 of formula (I), wherein R 3 is trifluoromethyl and R 1 , R 2 and (R 4 ) q As defined in Table M.

[0103] The compounds of formula (I) according to the invention are active ingredients having prophylactic and / or therapeutic value in the field of pest control. Even at low application rates, they have a very favorable biocidal spectrum and are well tolerated by warm-blooded species, fish and plants. These active ingredients according to the invention act on all or individual developmental stages of normal sensitive as well as resistant animal pests (such as representatives of insects or Acarina). The insecticidal or acaricidal activity of the active ingredients according to the invention can manifest itself directly per se, i.e., the destruction of the pests occurs immediately or only after some time has passed (e.g., during molting); or indirectly, e.g., by reducing the oviposition and / or hatching rate.

[0104] Examples of the above-mentioned animal pests are:

[0105] From the order Acarina, for example,

[0106] Species of the genus Acalitus, Aculus, Acaricalus, Aceria, Acarus siro, Amblyomma, Argas, Boophilus, Brevipalpus, Bryobia, Calipitrimerus, Chorioptes, Dermanyssus gallinae, Dermatophagoides, Eotetranychus, Eriophyes, Hemitarsonemus, Hyalomma, Ixodes, Olygonychus, Ornithodoros, Polyphagotarsonemus latus, Panonychus, Phyllocoptruta oleivora, Phytonemus, Polyphagotarsonemus, Psoroptes, Rhipicephalus, Rhizoglyphus, Sarcoptes, Steneotarsonemus, Tarsonemus, and Tetranychus;

[0107] From the order Phthiraptera, for example,

[0108] Species of the genus Haematopinus, Linognathus, Pediculus, Pemphigus, and Phylloxera;

[0109] From Coleoptera, for example,

[0110] Species of the genus Agriotes, Amphimallon majale, Anomala orientalis, Species of the genus Anthonomus, Species of the genus Aphodius, Astylus atromaculatus, Species of the genus Ataenius, Atomaria linearis, Chaetocnema tibialis, Species of the genus Cerotoma, Species of the genus Conoderus, Species of the genus Cosmopolites, Cotinis nitida, Species of the genus Curculio, Species of the genus Cyclocephala, Species of the genus Dermestes, Species of the genus Diabrotica, Diloboderus abderus, Species of the genus Epilachna, Species of the genus Eremnus, Heteronychus arator, Hypothenemus hampei, Lagria vilosa, Leptinotarsa decemlineata, Species of the genus Lissorhoptrus, Species of the genus Liogenys, Species of the genus Maecolaspis, Maladera castanea, Species of the genus Megascelis, Melighetes aeneus, Species of the genus Melolontha, Myochrous armatus, Species of the genus Orycaephilus, Species of the genus Otiorhynchus, Species of the genus Phyllophaga, Species of the genus Phlyctinus, Species of the genus Popillia, Species of the genus Psylliodes, Rhyssomatus aubtilis, Species of the genus Rhizopertha, Scarabeidae, Species of the genus Sitophilus, Species of the genus Sitotroga) species of the genus Somaticus, species of the genus Cryptorhynchus, Sternerus subsignatus, species of the genus Tenebrio, species of the genus Tribolium, and species of the genus Trogoderma;.

[0111] from the order Diptera, for example,

[0112] species of the genus Aedes, species of the genus Anopheles, Antherigona soccata, Bactrocea oleae, Bibio hortulanus, species of the genus Bradysia, Calliphora erythrocephala, species of the genus Ceratitis, species of the genus Chrysomyia, species of the genus Culex, species of the genus Cuterebra, species of the genus Dacus, species of the genus Delia, Drosophila melanogaster, species of the genus Fannia, species of the genus Gastrophilus, Geomyza tripunctata, species of the genus Glossina, species of the genus Hypoderma, species of the genus Hyppobosca, species of the genus Liriomyza, species of the genus Lucilia, species of the genus Melanagromyza, species of the genus Musca, species of the genus Oestrus, species of the genus Orseolia, Oscinella frit, Pegomyia hyoscyami, species of the genus Phorbia, species of the genus Rhagoletis, Rivelia quadrifasciata, species of the genus Scatella, species of the genus Sciara, species of the genus Stomoxys, species of the genus Tabanus, species of the genus Tannia, and species of the genus Tipula;

[0113] from the Hemiptera, for example,

[0114] Acanthocoris scabrator, Acrosternum spp, Adelphocoris lineolatus, Aleurodes spp., Amblypelta nitida, Bathycoelia thalassina, Geocoris spp, Cimex spp, Clavigralla tomentosicollis, Creontiades spp, Distantiella theobroma, Dichelops furcatus, Dysdercus spp, Edessa spp, Euchistus spp., Eurydema pulchrum, Eurygaster spp, Halyomorpha halys, Horcias nobilellus, Leptocorisa spp, Lygus spp, Maconellicoccus hirsutus, Murgantia histrionic, Neomegalotomus spp, Nesidiocoris tenuis, Nezara spp, Nysius simulans, Oebalus spp, Piesma spp, Piezodorus guildinii, Rhodnius spp, Scotinophara spp., Thyanta spp, Triatoma spp, Vatiga illudens;

[0115] It should be noted that there are some species names in the original text that seem to be incomplete or have incorrect spellings. The above translation has tried to maintain the original content as much as possible while making the translation conform to English expression habits. If there are specific requirements for the accuracy of species names, it may need to be further verified and corrected according to relevant taxonomic information.Acyrthosium pisum, species of the genus Adalges, Agalliana ensigera, Talassius sp., species of the genus Aleurodicus, species of the genus Aleurocanthus, Aleurotrachelus socialis, Aleurothrixus floccosus, Aleyrodes brassicae, Amarasca biguttula, Idioscopus nitidulus, species of the genus Aspidiotus, Aphis gossypii, Bactericera cockerelli, species of the genus Bemisia, species of the genus Brachycaudus, Brevicoryne brassicae, species of the genus Cacopsylla, Cavariella aegopodii Scop., species of the genus Ceroplastes, Chrysomphalus aonidum, Chrysomphalus dictyospermi, species of the genus Cicadella, Cofana spectra, species of the genus Cryptomyzus, species of the genus Empoasca, Coccus hesperidum, Cicadella viridis, species of the genus Parabemisia, Diaphorina citri, Diuraphis noxia, species of the genus Dicyphus, species of the genus Empoasca, Eriosoma lanigerum, species of the genus Erythroneura, species of the genus Gascardia, Glycaspis brimblecombei, Hyadaphis pseudobrassicae, species of the genus Hyalopterus, Hyperomyzus pallidus, Idioscopus clypealis, species of the genus Idiocerus, species of the genus Laodelphax, Sphaerolecanium prunastri, species of the genus Lepidosaphes, Lipaphis erysimi, Lyogenys maidis, species of the genus Macrosiphum, species of the genus Clovia, Metcalfa pruinosa, Metopolophium dirhodum, Metcalfa pruinosa, species of the genus Myzus, Neotoxoptera sp, species of the genus Nephotettix, species of the genus Nilaparvata)、Green aphid of Pyrus pyrifolia, Odonaspis ruthae, Melanaphis sacchari, Aleurotuberculatus lagerstroemiae, Psylla kotinskyi, species of Parlatoriza, species of Pemphigus, Ledra aurita, species of Idiocerus, Phorodon humuli, species of Phylloxera spp, species of Planococcus, species of Pseudaulacaspis, species of Pseudococcus, Pseudatomoscelis seriatus, species of Psylla, Pulvinaria aethiopica, species of Prionaspis, Quesada gigas, Recilia dorsalis, species of Rhopalosiphum, species of Saissetia, species of Scaphoideus, species of Schizaphis, species of Sitobion spp., Sogatella furcifera, Spissistilus festinus, Tarophagus Proserpina, species of Thecabius, species of Trialeurodes, Tridiscussporoboli, species of Trionymus, African Psylla, Unaspis yanonensis, Matsumurasca flammulina, Zyginidia scutellaris;.

[0116] From Hymenoptera, for example,

[0117] Acromyrmex, species of Arge spp., species of Atta spp., species of Cephus spp., species of Diprion spp., Diprionidae, Gilpinia polytoma, species of Hoplocampa spp., species of Lasius spp., Monommorium pharaonis, species of Neodiprion spp., species of Pogonomyrmex spp, Solenopsis invicta, species of Solenopsis spp., and species of Vespa spp.;

[0118] From Isoptera, for example,

[0119] Species of the genus Coptotermes, Corniternes cumulans, species of the genus Incisitermes, species of the genus Macrotermes, species of the genus Mastotermes, species of the genus Microtermes, species of the genus Reticulitermes; Solenopsis geminate

[0120] From the order Lepidoptera, for example,

[0121] Species of the genus Adoxophyes, species of the genus Pandemis, species of the genus Synanthedon, species of the genus Agrotis, cotton leafworm, species of the genus Amylois, bean pod borer, species of the genus Archips, species of the genus Argyresthia (Argyresthia spp.), species of the genus Adoxas, species of the genus Autographa, cotton leaf miner, maize stalk borer, Indian meal moth, oriental fruit moth, species of the genus Chilo, species of the genus Choristoneura, Chrysoteuchia topiaria, grape berry moth, species of the genus Cnaphalocrocis, species of the genus Cnephasia, species of the genus Cochylis, species of the genus Coleophora, Colias lesbia, Cosmophila flava, species of the genus Crambus, diamondback moth, Platynota stultana, box tree moth, species of the genus Eudemis, Cylas formicarius, species of the genus Elasmopalpus (Elasmopalpus lignosellus), sweet potato stem borer, species of the genus Ephestia, species of the genus Epinotia (Epinotia spp.), Estigmene acrea, Etiella zinckenella, species of the genus Eucosma, Ancylis comptana, species of the genus Euproctis, species of the genus Agrotis, Feltia jaculiferia, species of the genus Grapholita (Grapholita spp.), Homona magnanima, species of the genus Helicoverpa, diamondback moth, species of the genus Herpetogramma (Herpetogramma spp.), fall webworm, tomato fruitworm, Lasmopalpus lignosellus, leaf miner, species of the genus Lyonetia, Lobesia botrana, Loxostege bifidalis, species of the genus Lymantria, species of the genus Lyonetia, species of the genus Malacosoma (Malacosoma spp.), cabbage moth, tobacco hornworm, species of the genus Mythimna (Mythimna spp.), species of the genus Noctua, species of the genus Operophtera, Orniodes indica, European corn borer, species of the genus Petrophila, species of the genus Pandemis, Earias vittella, stem borer, pink bollworm, coffee leaf miner, armyworm, potato tuberworm, cabbage white, species of the genus Pieris, diamondback moth, species of the genus Spilonota, species of the genus Syrichthysa, Rachiplusia nu, Richia albicosta, species of the genus Scirpophaga (Scirpophaga spp.), species of the genus Sesamia, species of the genus Sparganothis, species of the genus Spodoptera, cabbage looper, species of the genus Synanthedon, species of the genus Heterocampa, species of the genus Adoxophyes, cabbage looper, tomato leafminer, and species of the genus Yponomeuta;

[0122] from the order Mallophaga, for example,

[0123] Species of Damalinea and Trichodectes;

[0124] From the order Orthoptera, for example,

[0125] Species of Blatta, Blattella, Gryllotalpa, Leucophaea maderae, Locusta, Neocurtilla hexadactyla, Periplaneta, Scapteriscus, and Schistocerca;

[0126] From the order Psocoptera, for example,

[0127] Species of Liposcelis;

[0128] From the order Siphonaptera, for example,

[0129] Species of Ceratophyllus, Ctenocephalides, and Xenopsylla cheopis;

[0130] From the order Thysanoptera, for example,

[0131] Calliothrips phaseoli, species of Frankliniella, Heliothrips, Hercinothrips, Parthenothrips, Scirtothrips aurantii, Sericothrips variabilis, Taeniothrips, and Thrips;

[0132] From the order Thysanura, for example, Lepisma saccharina.

[0133] In another aspect, the present invention may also relate to a method for controlling damage to plants and parts thereof by plant parasitic nematodes (endoparasitic nematodes, semi-endoparasitic nematodes, and ectoparasitic nematodes), in particular the following plant parasitic nematodes, such as root knot nematodes, Meloidogyne hapla, Meloidogyne incognita, Meloidogyne javanica, Meloidogyne arenaria, and other root knot nematode species; cyst-forming nematodes, Globodera rostochiensis, and other Globodera species; Heterodera avenae, Heterodera glycines, Heterodera schachtii, Heterodera trifolii, and other Heterodera species; seed gall nematodes, Anguina species; stem and foliar nematodes, Aphelenchoides species; sting nematodes, Belonolaimus longicaudatus, and other Belonolaimus species; pine nematodes, Bursaphelenchus xylophilus, and other Bursaphelenchus species; ring nematodes, Criconema species, Criconemella species, Criconemoides species, Mesocriconema species; stem and bulb nematodes, Ditylenchus destructor, Ditylenchus dipsaci, and other Ditylenchus species; awl nematodes, Dolichodorus species;Spiral nematodes, Heliocotylenchus multicinctus, and other species of the genus Helicotylenchus; sheath and sheathoid nematodes, species of the genus Hemicycliophora, and species of the genus Hemicriconemoides; species of the genus Hirshmanniella; lancenematodes, species of the genus Hoploaimus; false rootknot nematodes, species of the genus Nacobbus; needle nematodes, Longidorus elongatus, and other species of the genus Longidorus; pin nematodes, species of the genus Pratylenchus; lesion nematodes, Pratylenchus neglectus, Pratylenchus penetrans, Pratylenchus curvitatus, Pratylenchus goodeyi, and other species of the genus Pratylenchus; burrowing nematodes, Radopholus similis, and other species of the genus Radopholus; reniform nematodes, Rotylenchus robustus, Rotylenchus reniformis, and other species of the genus Rotylenchus; species of the genus Scutellonema; stubby root nematodes, Trichodorus primitivus, and other species of the genus Trichodorus, Paratrichodorus; stunt nematodes, Tylenchorhynchus claytoni, Tylenchorhynchus dubius, and other species of the genus Tylenchorhynchus;Citrus nematodes, Tylenchulus species; Dagger nematodes, Xiphinema species; and other plant parasitic nematode species such as Subanguina spp., Hypsoperine spp., Macroposthonia spp., Melinius spp., Punctodera spp., and Quinisulcius spp.

[0134] The compounds of the present invention may also have activity against molluscs. Examples thereof include, for example, the family Ampullariidae; the family Arionidae (Arion (A. ater, A. circumscriptus, A. hortensis, A. rufus)); the family Bradybaenidae (Bradybaena fruticum); the genus Cepaea (C. hortensis, C. nemoralis); ochlodina; the genus Deroceras (D. agrestis, D. empiricorum, D. laeve, D. reticulatum); the genus Discus (D. rotundatus); Euomphalia; the genus Galba (G. trunculata); the genus Helicelia (H. itala, H. obvia); the family Helicidae (Helicigona arbustorum); Helicodiscus; the genus Helix (H. aperta); the genus Limax (L. cinereoniger, L. flavus, L. marginatus, L. maximus, L. tenellus); the genus Lymnaea; Milax (family Milacidae) (M. gagates, M. marginatus, M. sowerbyi); the genus Opeas; the genus Pomacea (P. canaticulata); the genus Vallonia and Zanitoides.

[0135] The active ingredients according to the invention can be used for controlling, i.e. containing or destroying pests of the above types, which pests occur particularly on plants, especially on useful plants and ornamental plants in agriculture, horticulture and forestry, or on organs of these plants, such as fruits, flowers, leaves, stems, tubers or roots, and in some cases even plant organs formed at a subsequent time point remain protected against these pests.

[0136] In particular, suitable target crops are cereals such as wheat, barley, rye, oats, rice, maize or sorghum; sugar beet such as sugar beet or fodder beet; fruit such as pomes, drupes or berries, such as apples, pears, plums, peaches, apricots, cherries or berries such as strawberries, raspberries or blackberries; leguminous crops such as kidney beans, lentils, peas or soybeans; oil crops such as rape, mustard, poppy, olive, sunflower, coconut, castor, cocoa or groundnut; cucurbitaceous crops such as pumpkins, cucumbers or melons; fibre plants such as cotton, flax, hemp or jute; citrus fruits such as oranges, lemons, grapefruits or tangerines; vegetables such as spinach, lettuce, asparagus, cabbages, carrots, onions, tomatoes, potatoes or sweet peppers; lauraceae such as avocado, cinnamon or camphor; and also tobacco, nuts, coffee, eggplants, sugar cane, tea, pepper, grapevines, hops, plantain and latex plants.

[0137] In a specific embodiment, the compounds of formula (I) control mites, rust mites and spider mites in crops, trees and plants selected from vegetables (especially tomatoes and cucurbits), citrus, pomes, drupes, nuts, cotton, tropical crops, avocado, ornamental plants, kidney beans, soybeans, strawberries and grapes.

[0138] The compositions and / or methods of the present invention can also be used on any ornamental plants and / or vegetable crops (including flowers, shrubs, broad-leaved trees and evergreens).

[0139] For example, the present invention can be used for any of the following ornamental plant species: Ageratum species, Alonsoa spp., Anemone species, Anisodontea capsenisis, Anthemis species, Antirrhinum species, Aster species, Begonia species (such as Rieger begonias, wax begonias, tuberous begonias (B. tubéreux)), Bougainvillea species, Brachycome spp., Brassica species (ornamental plants), Calceolaria species, Capsicum, Catharanthus roseus, Canna species, Centaurea species, Chrysanthemum species, Cineraria maritima, Coreopsis species, Crassula coccinea, Cuphea ignea, Dahlia species, Delphinium species, Dicentra spectabilis, Dorotheantus spp., Eustoma grandiflorum, Forsythia species, Fuchsia species, Geranium gnaphalium, Gerbera species, Gomphrena globosa, Heliotropium species, Helianthus species, Hibiscus species, Hydrangea macrophylla, Hydrangea paniculata, Hypoestes phyllostachya, Impatiens walleriana, Iresines spp., Kalanchoe species, Lantana camara, Malva sylvestris, Osteospermum ecklonis, Lilium species, Lampranthus species, Mimulus species, Monarda species, Nemesia species, Tagetes species, Dianthus caryophyllus, Canna species, Oxalis species, Bellis perennis, Pelargonium species (Pelargonium peltatum, Pelargonium zonale), Viola tricolor, Petunia hybrida, Phlox paniculata, Plecthranthus spp., Euphorbia pulcherrima, Parthenocissus species (Parthenocissus quinquefolia, Parthenocissus tricuspidata), Primula species, Ranunculus species, Rhododendron species, Rosa species (Rosa rugosa), Rudbeckia species, Saintpaulia ionantha, Salvia species, Scaevola aemola, Schizanthus wisetonensis, Sedum species, Solanum species, Surfinia spp., Tagetes species, Nicotiana species, Verbena species, Zinnia species, and other flower bed plants.

[0140] For example, the present invention can be used for any of the following vegetable species: Allium species (garlic, onion, A. oschaninii, leek, scallion, Welsh onion), Pimpinella anisum, Apium graveolens, Asparagus officinalis, Beta vulgaris, Brassica species (cabbage, Chinese cabbage, turnip), Capsicum annuum, Cicer arietinum, Cichorium endivia, Cichorium species (Cichorium intybus, Cichorium endivia), Citrullus lanatus, Cucumis species (Cucumis sativus, Cucumis melo), Cucurbita species (Cucurbita pepo, Cucurbita maxima), Cynara species (Cynara scolymus, Cynara cardunculus), Daucus carota, Foeniculum vulgare, Hypericum species, Lactuca sativa, Lycopersicon species (Lycopersicon esculentum, Lycopersicon pimpinellifolium), Mentha species, Ocimum basilicum, Petroselinum crispum, Phaseolus species (Phaseolus vulgaris, Phaseolus coccineus), Pisum sativum, Raphanus sativus, Rheum rhabarbarum, Rosmarinus officinalis, Salvia species, Tragopogon porrifolius, Solanum melongena, Spinacia oleracea, Valerianella species (Valerianella locusta, V. eriocarpa), and Vicia faba.

[0141] Preferred ornamental plant species include Saintpaulia ionantha, Begonia species, Dahlia species, Gerbera species, Hydrangea species, Verbena species, Rosa species, Kalanchoe species, Euphorbia pulcherrima, Aster species, Centaurea species, Coreopsis species, Delphinium species, Monarda species, Phlox species, Tagetes species, Sedum species, Petunia species, Viola species, Impatiens species, Geranium species, Chrysanthemum species, Ranunculus species, Fuchsia species, Salvia species, Hydrangea macrophylla, Rosmarinus officinalis, Salvia officinalis, Hypericum perforatum, Mentha spicata, Capsicum annuum, Lycopersicon esculentum, and Cucumis sativus.

[0142] These active ingredients according to the invention are particularly suitable for controlling Aphis craccivora, Diabrotica undecimpunctata howardi, Heliothis virescens, Myzus persicae, Plutella xylostella, and Spodoptera litura on cotton, vegetable, maize, rice, and soybean crops. These active ingredients according to the invention are additionally particularly suitable for controlling Mamestra brassicae (preferably on vegetables), Cydia pomonella (preferably on apples), Empoasca flavescens (preferably on vegetables, in vineyards), Leptinotarsa decemlineata (preferably on potatoes), and Chilo suppressalis (preferably on rice).

[0143] Compounds having formula (I) are particularly suitable for controlling: mites, spider mites and rust mites, for example, species of the genus Apioseius; Apioseius woodi; Acarus siro; species of the genus Tyrophagus; Phyllocoptruta oleivora; Aculus sheldoni; species of the genus Aculus; Epitrimerus pyri; species of the genus Epitrimerus; Amblyseius fallacis; species of the genus Brevipalpus; Brevipalpus phoenicis; Bryobia praetiosa; Bryobia rubrioculus; species of the genus Carpoglyphus; Cheyletiella blakei; species of the genus Cheyletiella; Cheyletiella yasguri; Dermatophagoides pteronyssinus; species of the genus Dermatophagoides; species of the genus Histiostoma; Demodex bovis; Demodex caballi; Demodex canis; Demodex caprae; Demodex equi; Demodex ovis; species of the genus Demodex; Demodex phylloides; Dermanyssus gallinae; species of the genus Dermanyssus; Eriophyes pyri; Eriophyes ribis; species of the genus Eriophyes; Eriophyes vitis; species of the genus Eutetranychus; Halotydeus destructor; species of the genus Hemitarsonemus; species of the genus Ornithonyssus; species of the genus Poultry; Neoschongastia xerothermobia; Neotrombicula autumnalis; Neotrombicula desaleri; Notoedres cati; species of the genus Notoedres; Oligonychus coffeae; Oligonychus ilicis; species of the genus Oligonychus; species of the genus Ornithocheyletia; Ornithonyssus bursa; species of the genus Ornithonyssus; Ornithonyssus sylviarum; Otodectes cynotis; species of the genus Otodectes; Panonychus citri; species of the genus Panonychus; Panonychus ulmi; Phyllacarus citri; species of the genus Phyllacarus; species of the genus Phytoseiulus; Pneumonyssoides caninum; Polyphagotarsonemus latus; species of the genus Polyphagotarsonemus; Psorergates ovis; species of the genus Psorergates; Psoroptes cuniculi; Psoroptes equi; Psoroptes ovis; species of the genus Psoroptes; Psoroptes rupicaprae; Sarcoptes bovis; Sarcoptes canis; Sarcoptes caprae; Sarcoptes equi; Sarcoptes ovis; Sarcoptes scabiei; Sarcoptes suis; Stenotarsonemus spinki; species of the genus Stenotarsonemus; species of the genus Thoracotarsonemus; species of the genus Tarsonemus; Tetranychus cinnabarinus; Tetranychus kanzawai; species of the genus Tetranychus; Tetranychus urticae; Trombicula akamushi; species of the genus Trombicula; Typhlodromus occidentalis; species of the genus Tyrophagus; Varroa jacobsoni; species of the genus Varroa; Vasates lycopersici; and Zetzellia mali.

[0144] In an embodiment, a compound having formula (I) is particularly suitable for controlling one or more of the following: Phyllocoptruta oleivora; Aculus lycopersici; Aculus pelekassi; Aculus schlechtendali; Brevipalpus phoenicis; Brevipalpus species; Bryobia praetiosa; Eotetranychus carpini; Eotetranychus species; Epitrimerus pyri; Eriophyes piri; Eriophyes species; Colomerus vitis; Eutetranychus africanus; Eutetranychus orientalis; Oligonychus pratensis; Panonychus citri; Panonychus ulmi; Calepitrimerus vitis; Phyllocoptruta oleivora; Polyphagotarsonemus latus; Tetranychus cinnabarinus; Tetranychus kanzawai; Tetranychus species; and Tetranychus urticae.

[0145] In another embodiment, a compound having formula (I) is even more particularly suitable for controlling one or more of the following: Phyllocoptruta oleivora; Aculus pelekassi; Brevipalpus phoenicis; Brevipalpus species; Eriophyes piri; Colomerus vitis; Eutetranychus africanus; Eutetranychus orientalis; Oligonychus pratensis; Panonychus ulmi; Calepitrimerus vitis; Phyllocoptruta oleivora; Polyphagotarsonemus latus; Tetranychus cinnabarinus; Tetranychus kanzawai; Tetranychus species; and Tetranychus urticae.

[0146] The term "crop" should be understood to also include crop plants that have been so transformed by the use of recombinant DNA techniques that they are capable of synthesizing one or more selectively acting toxins, such as are known, for example, from toxin-producing bacteria, in particular those of the genus Bacillus.

[0147] Toxins that can be expressed by such transgenic plants include, for example, insecticidal proteins, such as insecticidal proteins from Bacillus cereus or Bacillus popilliae; or insecticidal proteins from Bacillus thuringiensis, such as δ-endotoxins, for example Cry1Ab, Cry1Ac, Cry1F, Cry1Fa2, Cry2Ab, Cry3A, Cry3Bb1 or Cry9C, or vegetative insecticidal proteins (Vip), for example Vip1, Vip2, Vip3 or Vip3A; or insecticidal proteins that colonize nematodes by bacteria, such as Photorhabdus spp. or Xenorhabdus spp., such as Photorhabdus luminescens, Xenorhabdus nematophilus; toxins produced by animals, such as scorpion toxins, spider toxins, bee toxins and other insect-specific neurotoxins; toxins produced by fungi, such as streptomyces toxins, lectins, such as pea lectin, barley lectin or snowdrop lectin; agglutinin; protease inhibitors, such as trypsin inhibitor, serine protease inhibitor, potato protease inhibitor, cystatin, papain inhibitor; ribosome-inactivating proteins (RIP), such as ricin, maize-RIP, abrin, luffin, saporin or bryodin; steroid metabolic enzymes, such as 3-hydroxy steroid oxidase, ecdysteroid-UDP-glycosyl-transferase, cholesterol oxidase, ecdysis inhibitor, HMG-COA-reductase, ion channel blockers such as sodium channel or calcium channel blockers, juvenile hormone esterase, diuretic hormone receptor, stilbene synthase, bibenzyl synthase, chitinase and glucanase.

[0148] In the context of the present invention, δ-endotoxins (for example Cry1Ab, Cry1Ac, Cry1F, Cry1Fa2, Cry2Ab, Cry3A, Cry3Bb1 or Cry9C) or vegetative insecticidal proteins (Vip) (for example Vip1, Vip2, Vip3 or Vip3A) should be understood to clearly also include hybrid toxins, truncated toxins and modified toxins. Hybrid toxins are recombinantly produced by new combinations of different domains of those proteins (see, for example, WO 02 / 15701). Truncated toxins, such as truncated Cry1Ab, are known. In the case of modified toxins, one or more amino acids of the naturally occurring toxin are replaced. In such amino acid substitutions, preferably a non-naturally occurring protease recognition sequence is inserted into the toxin, for example in the case of Cry3A055, a cathepsin-G-recognition sequence is inserted into the Cry3A toxin (see WO 03 / 018810).

[0149] Examples of such toxins or transgenic plants capable of synthesizing such toxins are disclosed, for example, in EP - A - 0 374 753, WO 93 / 07278, WO 95 / 34656, EP - A - 0 427 529, EP - A - 451 878 and WO 03 / 052073.

[0150] Methods for preparing such transgenic plants are generally known to those skilled in the art and are described, for example, in the above - mentioned publications. CryI - type deoxyribonucleic acids and their preparation are known, for example, from WO 95 / 34656, EP - A - 0 367 474, EP - A - 0 401 979 and WO 90 / 13651.

[0151] The toxins contained in transgenic plants render the plants tolerant to harmful insects. Such insects can be present in any insect taxon, but are particularly common among beetles (Coleoptera), dipterous insects (Diptera) and moths (Lepidoptera).

[0152] Transgenic plants containing one or more genes encoding insecticide resistance and expressing one or more toxins are known and some of them are commercially available. Examples of such plants are: (maize variety expressing the Cry1Ab toxin); YieldGard (maize variety expressing the Cry3Bb1 toxin); YieldGard (maize variety expressing the Cry1Ab and Cry3Bb1 toxins); (maize variety expressing the Cry9C toxin); Herculex (maize variety expressing the Cry1Fa2 toxin and the enzyme phosphinothricin N - acetyltransferase (PAT) conferring tolerance to the herbicide glufosinate ammonium); NuCOTN (cotton variety expressing the Cry1Ac toxin); Bollgard (cotton variety expressing the Cry1Ac toxin); Bollgard (cotton variety expressing the Cry1Ac and Cry2Ab toxins); (cotton variety expressing the Vip3A and Cry1Ab toxins); (potato variety expressing the Cry3A toxin); GT Advantage (GA21 glyphosate - tolerant trait), CB Advantage (Bt11 corn borer (CB) trait) and

[0153] Additional examples of such genetically modified crops are:

[0154] 1. Bt11 maize, from Syngenta Seeds SAS, Chemindel'Hobit 27, F-31 790 St. Sauveur, France, registration number C / FR / 96 / 05 / 10. Genetically modified maize that expresses a truncated Cry1Ab toxin by transgene, making it resistant to the attack of European corn borer (Ostrinia nubilalis and Sesamia nonagrioides). Bt11 maize also expresses the PAT enzyme by transgene to obtain tolerance to the herbicide glufosinate.

[0155] 2. Bt176 maize, from Syngenta Seeds, Chemindel'Hobit 27, F-31 790 St. Sauveur, France, registration number C / FR / 96 / 05 / 10. Genetically modified maize that expresses the Cry1Ab toxin by transgene, making it resistant to the attack of European corn borer (Ostrinia nubilalis and Sesamia nonagrioides). Bt176 maize also expresses the enzyme PAT by transgene to obtain tolerance to the herbicide glufosinate.

[0156] 3. MIR604 maize, from Syngenta Seeds, Chemindel'Hobit 27, F-31 790 St. Sauveur, France, registration number C / FR / 96 / 05 / 10. Maize with insect resistance by expressing a modified Cry3A toxin by transgene. This toxin is Cry3A055 modified by inserting a cathepsin-G-protease recognition sequence. The preparation of such genetically modified maize plants is described in WO 03 / 018810.

[0157] 4. MON 863 maize, from Monsanto Europe S.A., Avenue de Tervuren 270-272, B-1150 Brussels, Belgium, registration number C / DE / 02 / 9. MON 863 expresses the Cry3Bb1 toxin and is resistant to certain Coleoptera insects.

[0158] 5. IPC 531 cotton, from Monsanto Europe, Avenue de Tervuren 270-272, B-1150 Brussels, Belgium, registration number C / ES / 96 / 02.

[0159] 6.1507 Maize, from Pioneer Overseas Corporation, Avenue Tedesco, 7B - 1160 Brussels, Belgium, registration number C / NL / 00 / 10. Genetically modified maize expressing the protein Cry1F to obtain resistance to certain Lepidoptera insects and expressing the PAT protein to obtain tolerance to the herbicide glufosinate.

[0160] 7. NK603×MON 810 Maize, from Monsanto Europe S.A., 270 - 272 Avenue de Tervuren, B - 1150 Brussels, Belgium, registration number C / GB / 02 / M3 / 03. Composed of a conventionally bred hybrid maize variety by crossing the genetically modified varieties NK603 and MON 810. NK603×MON 810 maize transgenically expresses the protein CP4EPSPS obtained from Agrobacterium sp. strain CP4, making it tolerant to the herbicide (containing glyphosate), and also the Cry1Ab toxin obtained from Bacillus thuringiensis subsp. kurstaki, making it tolerant to certain Lepidoptera insects, including the European corn borer.

[0161] Transgenic crops of insect - resistant plants are also described in the report 2003 of BATS (Zentrum für Biosicherheit und Nachhaltigkeit, Zentrum BATS, Clarastrasse 13, Basel 4058, Switzerland) http: / / bats.ch )

[0162] The term "crop" should be understood to also include crop plants that have been so transformed by the use of recombinant DNA technology that they are able to synthesize antipathogenic substances with selective action, which are, for example, so - called "pathogenesis - related proteins" (PRPs, see, for example, EP - A - 0 392 225). Examples of such antipathogenic substances and transgenic plants capable of synthesizing such antipathogenic substances are known, for example, from EP - A - 0 392 225, WO 95 / 33818, and EP - A - 0 353191. The methods for producing such transgenic plants are generally known to those skilled in the art and are described, for example, in the above - mentioned publications.

[0163] Crops can also be modified to enhance resistance to fungal (e.g., Fusarium, Colletotrichum, or Phytophthora), bacterial (e.g., Pseudomonas) or viral (e.g., potato leafroll virus, tomato spotted wilt virus, cucumber mosaic virus) pathogens.

[0164] The crops also include those crops having enhanced resistance to nematodes, such as Heterodera glycines.

[0165] Crops having tolerance to abiotic stress include, for example, those crops having enhanced tolerance to drought, high salt, high temperature, cold, frost or light radiation through the expression of NF-YB or other proteins known in the art.

[0166] Antipathogenic substances that can be expressed by such transgenic plants include, for example, ion channel blockers, such as blockers of sodium channels and calcium channels, such as the viral KP1, KP4 or KP6 toxins; stilbene synthase; bibenzyl synthase; chitinase; glucanase; so-called "pathogenesis-related proteins" (PRPs; see, for example, EP-A-0 392 225); antipathogenic substances produced by microorganisms, such as peptide antibiotics or heterocyclic antibiotics (see, for example, WO 95 / 33818) or protein or polypeptide factors involved in plant pathogen defense (so-called "plant disease resistance genes", as described in WO 03 / 000906).

[0167] A further field of use of the compositions according to the invention is the protection of stored articles and storage rooms and the protection of raw materials, such as wood, textiles, floors or buildings, and also in the hygiene field, in particular the protection of humans, livestock and productive animals against pests of the type mentioned.

[0168] The present invention provides compounds of the first aspect for therapy. The present invention provides compounds of the first aspect for controlling parasites in or on the body of an animal. The present invention further provides compounds of the first aspect for controlling ectoparasites of an animal. The present invention further provides compounds of the first aspect for preventing and / or treating diseases transmitted by ectoparasites.

[0169] The present invention provides the use of the compounds of the first aspect in the manufacture of a medicament for controlling parasites in or on the body of an animal. The present invention further provides the use of the compounds of the first aspect in the manufacture of a medicament for controlling ectoparasites of an animal. The present invention further provides the use of the compounds of the first aspect in the manufacture of a medicament for preventing and / or treating diseases transmitted by ectoparasites.

[0170] The present invention provides the use of the compounds of the first aspect in controlling parasites in or on the body of an animal. The present invention further provides the use of the compounds of the first aspect in controlling ectoparasites of an animal.

[0171] When used in the context of parasites in or on the body of an animal, the term "control" means reducing the number of pests or parasites, eliminating the pests or parasites and / or preventing further infestation by pests or parasites.

[0172] When used in the context of parasites in or on an animal, the term "treatment" means inhibiting, slowing, halting, or reversing the progression or severity of existing symptoms or disease.

[0173] When used in the context of parasites in or on an animal, the term "prevention" means avoiding the development of symptoms or disease in an animal.

[0174] When used in the context of parasites in or on an animal, the term "animal" may refer to mammals and non-mammals, such as birds or fish. In the case of mammals, it can be a human or a non-human mammal. Non-human mammals include, but are not limited to, domestic animals and pets. Domestic animals include, but are not limited to, cattle, camels, pigs, sheep, goats, and horses. Pets include, but are not limited to, dogs, cats, and rabbits.

[0175] "Parasits" are harmful organisms that live in or on a host animal and benefit by obtaining nutrients at the expense of the host animal. "Endoparasites" are parasites that live inside a host animal. "Exoparasites" are parasites that live on the surface of a host animal. Exoparasites include, but are not limited to, ticks, insects, and crustaceans (e.g., sea lice). The subclass Acarina (or Acarina) includes ticks and mites. Ticks include, but are not limited to, members of the genus Rhipicaphalus, such as Rhipicaphalus microplus (Boophilus microplus) and Rhipicephalus sanguineus; Amblyomrna; Dermacentor; Haemaphysalis; Hyalomma; Ixodes; Rhipicentor; Margaropus; Argas; Otobius; and Ornithodoros. Mites include, but are not limited to, members of the following genera: Dermestes, such as Dermestes gallinae; Itch, such as Sheep; Cheyletus; Dermatosus; such as Dermatosus gallinae; Ortnithonyssus; Demodex, such as Demodex canis; Sarcoptes, such as Sarcoptes hominis; and Psora. Insects include, but are not limited to, members of the following orders: Siphonaptera, Diptera, Trichoderma, Lepidoptera, Coleoptera, and Homoptera. Members of Siphonaptera include, but are not limited to, Ctenocephatides canis and Ctenocephatides canis. Members of Diptera include, but are not limited to, species of the genus Musca; Skin flies, such as horse flies and sheep flies; Biting flies; Gadflies, such as Tabunus species and Tabunus species; Black horn flies, such as Haematobium; Stomoxys; Lucilia; Midges; and mosquitoes. Members of the order Trichoderma include, but are not limited to, blood-sucking lice and chewing lice, such as the wool lice (Bovicola Ovis) and the cattle feather lice.

[0176] As used in the context of parasites in or on an animal, the term "effective amount" refers to the amount or dose of a compound or salt thereof of the present invention which, when administered to an animal in a single dose or multiple doses, provides the desired effect in or on the animal. A treating diagnostician (as a person skilled in the art) can readily determine the effective amount by using known techniques and by observing results obtained in comparable circumstances. In determining the effective amount, the treating diagnostician takes into account a number of factors including, but not limited to: the species of mammal; its size, age and general health; the parasite to be controlled and the degree of infestation; the particular disease or disorder involved; the extent or severity of the disease or disorder; the individual response; the particular compound administered; the mode of administration; the bioavailability characteristics of the dosage formulation; the dosage regimen selected; the use of concomitant medications; and other relevant circumstances.

[0177] The compounds of the present invention can be administered to an animal by any route that provides the desired effect, including but not limited to topically, orally, parenterally and subcutaneously. Topical administration is preferred. Formulations suitable for topical administration include, for example, solutions, emulsions and suspensions, and can take the form of pouring, spot-on, spraying, spray race or dipping. In an alternative, the compounds of the present invention can be administered by an ear tag or a collar.

[0178] The salt forms of the compounds of the present invention include both pharmaceutically acceptable salts and veterinarily acceptable salts, which may be different from agrochemically acceptable salts. Pharmaceutically and veterinarily acceptable salts and common methods for preparing them are well known in the art. See, for example, Gould, P.L., "Salt selection for basic drugs", International Journal of Pharmaceutics, 33:201-217 (1986); Bastin, R.J. et al. "Salt Selection and Optimization Procedures for Pharmaceutical New Chemical Entities", Organic Process Research and Development, 4:427-435 (2000); and Berge, S.M. et al., "Pharmaceutical Salts", Journal of Pharmaceutical Sciences, 66:1-19, (1977). Those skilled in the art of synthesis will understand that, using techniques and conditions well known to those of ordinary skill in the art, the compounds of the present invention are readily convertible to salts and can be isolated as salts (such as hydrochlorides). In addition, those skilled in the art of synthesis will understand that the compounds of the present invention are readily convertible to the corresponding free bases and can be isolated from the corresponding salts as the corresponding free bases.

[0179] The present invention also provides methods for controlling pests (such as mosquitoes and other disease vectors; see also http: / / www.who.int / malaria / vector_control / irs / en / ). In one embodiment, the method for controlling pests includes applying the composition of the present invention to the target pests, their habitats or surfaces or substrates by brushing, rolling, spraying, coating or dipping. By way of example, IRS (indoor residual spraying) application to surfaces (such as wall, ceiling or floor surfaces) is contemplated by the method of the present invention. In another embodiment, application of such a composition to substrates such as non-woven or fabric materials in the form of netting, coverings, bedding, curtains and tents (or for use in the manufacture of these articles) is contemplated.

[0180] In one embodiment, a method for controlling such pests includes applying a pesticidally effective amount of the composition of the present invention to the target pests, their habitats or surfaces or substrates, so as to provide effective residual pesticidal activity on the surface or substrate. Such application can be carried out by brushing, rolling, spraying, coating or dipping the pesticidal composition of the present invention. By way of example, IRS application to surfaces such as wall, ceiling or floor surfaces is contemplated by the method of the present invention so as to provide effective residual pesticidal activity on the surface. In another embodiment, application of such a composition for residual control of pests on substrates which are fabric materials in the form of, for example, netting, coverings, bedding, curtains and tents (or which can be used in the manufacture of these articles) is contemplated.

[0181] The substrates to be treated (including nonwovens, fabrics or netting) can be made of natural fibers such as cotton, raffia leaf fiber, jute, linen, sisal, hessian or wool, or synthetic fibers such as polyamide, polyester, polypropylene, polyacrylonitrile and the like. Polyester is particularly suitable. Methods of treating textiles are known, for example WO 2008 / 151984, WO2003 / 034823, US 5631072, WO 2005 / 64072, WO 2006 / 128870, EP 1724392, WO 2005113886 or WO 2007 / 090739.

[0182] Another field of use of the composition according to the invention is the field of tree injection / trunk treatment for all ornamental trees together with all kinds of fruit trees and nut trees.

[0183] In the field of tree injection / trunk treatment, the compounds according to the invention are particularly suitable for combating wood-boring insects from the Lepidoptera mentioned above and from the Coleoptera, in particular for combating the wood-boring beetles listed in Tables A and B below:

[0184] Table A. Examples of exotic wood-boring beetles of economic importance.

[0185]

[0186] Table B. Examples of native wood-boring beetles of economic importance.

[0187]

[0188]

[0189]

[0190] The present invention can also be used to control any insect pests that can be present in turfgrass, including, for example, beetles, caterpillars, fire ants, ground pearls, millipedes, pill bugs, mites, mole crickets, scale insects, mealybugs, ticks, froghoppers, southern green stink bugs, and white grubs. The present invention can be used to control insect pests at all stages of their life cycle, including eggs, larvae, nymphs, and adults.

[0191] In particular, the present invention can be used to control insect pests that feed on the roots of turfgrass, including white grubs (such as species of Cyclocephala (e.g., masked chafers, C. lurida), species of Rhizotrogus (e.g., European chafer, R. majalis), species of Cotinis (e.g., Green June beetle, C. nitida), species of Popillia (e.g., Japanese beetle, P. japonica), species of Phyllophaga (e.g., May / June beetles), species of Serica (e.g., Blackturfgrass ataenius, velvetbean caterpillar), species of Maladera (e.g., Asiatic garden beetle, chestnut-colored Maladera), and species of Tomarus), ground pearls (species of Margarodes), mole crickets (tan, southern, and short-winged; species of Scapteriscus, Gryllotalpa africana), and leatherjackets (European crane fly, species of Tipula).

[0192] The present invention can also be used to control insect pests in turfgrass of thatched dwellings, and these insect pests include armyworms (such as fall armyworm, Spodoptera frugiperda, and common armyworm, Pseudaletia unipuncta), cutworms, weevils (Sphenophorus spp., such as S. venatus verstitus and S. parvulus), and grass moths (such as Crambus spp. and tropical sod webworm, Herpetogramma phaeopteralis).

[0193] The present invention can also be used to control insect pests in turfgrass that live on the ground and feed on the leaves of turfgrass, and these insect pests include wheat bugs (such as southern wheat bug, Blissus insularis), Bermudagrass mite (Eriophyes cynodoniensis), Antonina graminis, Propsapia bicincta, leafhoppers, cutworms (Noctuidae), and Schizaphis graminum.

[0194] The present invention can also be used to control other pests in turfgrass, such as imported fire ant (Solenopsis invicta) that creates ant nests in the turf.

[0195] In the field of hygiene, the composition according to the present invention is effective against ectoparasites such as hard ticks, soft ticks, Sarcoptes scabiei, harvest mites, flies (biting and licking), parasitic fly larvae, lice, head lice, bird lice, and fleas.

[0196] Examples of such parasites are as follows:

[0197] Phthiraptera: species of Haematopinus, Linognathus spp., Pediculus spp., and Phtirus spp., and species of Syringophilidae.

[0198] Mallophaga: species of Trinoton, Menopon spp., Anaticola spp., Solenopotes spp., Werneckiella spp., Lepikentron spp., Damalinia spp., Trichodectes spp., and Felicola spp.

[0199] Diptera and Nematocerina and Brachycerina, such as Aedes spp., Anopheles spp., Culex spp., Simulium spp., Eusimulium spp., Phlebotomus spp., Lutzomyia spp., Culicoides spp., Chrysops spp., Hybomitra spp., Atylotus spp., Tabanus spp., Haematopota spp., Philipomyia spp., Braula spp., Musca spp., Hydrotaea spp., Stomoxys spp., Haematobia spp., Morellia spp., Fannia spp., Glossina spp., Calliphora spp., Lucilia spp., Chrysomyia spp., Wohlfahrtia spp., Sarcophaga spp., Oestrus spp., Hypoderma spp., Gasterophilus spp., Hippobosca spp., Lipoptena spp., and Melophagus spp.

[0200] Siphonapterida, such as Pulex spp., Ctenocephalides spp., Xenopsylla spp., Ceratophyllus spp.

[0201] Heteropterida, such as Cimex spp., Triatoma spp., Rhodnius spp., Panstrongylus spp.

[0202] Order Blattarida, such as Blatta orientalis, Periplaneta americana, Blattella germanica, and Supella spp.

[0203] Subclass Acaria (Order Acarida) and the orders Metastigmata and Mesostigmata, such as Argas spp., Ornithodorus spp., Otobius spp., Ixodes spp., Amblyomma spp., Boophilus spp., Dermacentor spp., Haemophysalis spp., Hyalomma spp., Rhipicephalus spp., Dermanyssus spp., Raillietia spp., Pneumonyssus spp., Sternostoma spp., and Varroa spp.

[0204] Actinedida (Prostigmata) and Acaridida (Astigmata), such as species of Acarapis spp., Cheyletiella spp., Ornithocheyletia spp., Myobia spp., Psorergates spp., Demodex spp., Trombicula spp., Listrophorus spp., Acarus spp., Tyrophagus spp., Caloglyphus spp., Hypodectes spp., Pterolichus spp., Psoroptes spp., Chorioptes spp., Otodectes spp., Sarcoptes spp., Notoedres spp., Knemidocoptes spp., Cytodites spp. and Laminosioptes spp.

[0205] The composition according to the invention is also suitable for protecting materials in situations such as wood, textiles, plastics, adhesives, glues, paints, paper and cardboard, leather, floors and buildings against insect infestation.

[0206] The compositions according to the invention can be used, for example, against the following pests: beetles such as Hylotrupes bajulus, Cerambycidae, Anobium punctatum, Xestobium rufovillosum, Ernobius mollis, Dendrobium pertinex, Trypodendron lineatum, Priobium carpini, Lyctus brunneus, Lyctus africanus, Lyctus sinensis, Lyctus linearis, Lyctus pubescens, Lyctus thoracicus, Lepidoxyla serricornis, Xyleborus species, Ips species, Hypothenemus hampei, Sinoxylon anale, Heterobostrychus brunneus, Scolytidae and Dinoderus minutus; and also Hymenoptera such as Sirex juvencus, Sirex noctilio, Sirex amicus and Urocerus augur; and termites such as Kalotermes flavicollis, Cryptotermes domesticus, Heterotermes indicola, Reticulitermes flaviceps, Reticulitermes santonensis, Reticulitermes lucifugus, Mastotermes darwiniensis, Archotermopsis laticeps and Coptotermes formosanus; and moths such as Lepisma saccharina. The compounds of formulae I and I'a, or salts thereof, are particularly suitable for controlling one or more pests selected from the families Noctuidae, Plutellidae, Chrysomelidae, Thripidae, Pentatomidae, Tortricidae, Delphacidae, Aphididae, Noctuidae, Crambidae, Meloidogynidae and Heteroderidae. In a preferred embodiment of each aspect, the compound TX (where the abbreviation "TX" means "a compound selected from the compounds defined in Tables 1 to 7 and Table P") controls one or more pests selected from the families Noctuidae, Plutellidae, Chrysomelidae, Thripidae, Pentatomidae, Tortricidae, Delphacidae, Aphididae, Noctuidae, Crambidae, Meloidogynidae and Heteroderidae.

[0207] The compounds of formulae I and I'a, or salts thereof, are particularly suitable for controlling one or more pests selected from the genera Spodoptera species, Plutella species, Frankliniella species, Thrips species, Euschistus species, Cydia species, Nilaparvata species, Myzus species, Aphis species, Diabrotica species, Rhopalosiphum species, Agrotis species and Chilo species. In a preferred embodiment of each aspect, the compound TX (where the abbreviation "TX" means "a compound selected from the compounds defined in Tables 1 to 7 and Table P") controls one or more pests selected from the genera Spodoptera species, Plutella species, Frankliniella species, Thrips species, Euschistus species, Cydia species, Nilaparvata species, Myzus species, Aphis species, Diabrotica species, Rhopalosiphum species, Agrotis species and Chilo species.

[0208] The compounds of formulae I and I'a, or salts thereof, are particularly suitable for controlling one or more of the following: Spodoptera litura, Plutella xylostella, Frankliniella occidentalis, Thrips tabaci, Euschistus heros, Cydia pomonella, Nilaparvata lugens, Myzus persicae, Agrotis segetum, Aphis glycines, Diabrotica vittata, Rhopalosiphum padi, and Chilo suppressalis.

[0209] In a preferred embodiment of each aspect, the compound TX (where the abbreviation "TX" means "a compound selected from the compounds defined in Tables 1 to 7 and Table P") controls one or more of the following: Spodoptera littoralis, Plutella xylostella, Frankliniella occidentalis, Thrips tabaci, Euschistus heros, Cydia pomonella, Nilaparvata lugens, Myzus persicae, Pseudoplusia includens, Aphis glycines, Diabrotica undecimpunctata howardi, Rhopalosiphum padi, and Chilo suppressalis, such as Spodoptera littoralis + TX, Plutella xylostella + TX, Frankliniella occidentalis + TX, Thrips tabaci + TX, Euschistus heros + TX, Cydia pomonella + TX, Nilaparvata lugens + TX, Myzus persicae + TX, Pseudoplusia includens + TX, Aphis glycines + TX, Diabrotica undecimpunctata howardi + TX, Rhopalosiphum padi + TX, and Chilo suppressalis + TX.

[0210] In an embodiment of each aspect, a compound from Tables 1 to 7 and Table P is suitable for controlling Spodoptera littoralis, Plutella xylostella, Frankliniella occidentalis, Thrips tabaci, Euschistus heros, Cydia pomonella, Nilaparvata lugens, Myzus persicae, Pseudoplusia includens, Aphis glycines, Diabrotica undecimpunctata howardi, Rhopalosiphum padi, and Chilo suppressalis on cotton, vegetable, corn, cereal, rice, and soybean crops.

[0211] In an embodiment, a compound from Tables 1 to 7 and Table P is suitable for controlling Mamestra (preferably on vegetables), Cydia pomonella (preferably on apples), Empoasca (preferably on vegetables, in vineyards), Leptinotarsa (preferably on potatoes), and Chilo suppressalis (preferably on rice).

[0212] The compounds according to the invention can have any number of benefits, including in particular a favorable level of biological activity for protecting plants against insects or superior properties for use as an active ingredient in agrochemicals (e.g., higher biological activity, favorable activity spectrum, increased safety (towards non-target organisms above and below ground such as fish, birds, and bees), improved physico-chemical properties, or increased biodegradability). In particular, it has been unexpectedly found that certain compounds of formula (I) can show favorable safety with respect to non-target arthropods, especially pollinators (such as honey bees, solitary bees, and bumblebees). Most particularly, with respect to Apis mellifera.

[0213] The compounds according to the invention can be used as pest control agents in their unmodified form, but they are generally formulated into compositions with formulation aids (such as carriers, solvents, and surface-active substances) in various ways. These formulations can be in different physical forms, for example, in the form of: dusts, gels, wettable powders, water-dispersible granules, water-dispersible tablets, effervescent compressed tablets, emulsifiable concentrates, microemulsifiable concentrates, oil-in-water emulsions, flowable oils, aqueous dispersions, oily dispersions, suspoemulsions, capsule suspensions, emulsifiable granules, soluble liquids, water-soluble concentrates (using water or water-miscible organic solvents as carriers), impregnated polymer films, or in other known forms, for example, known from the Manual on Development and Use of FAO and WHO Specifications for Pesticides, United Nations, 1st edition, second revision (2010). Such formulations can be used directly or can be diluted before use. Dilution can be carried out with, for example, water, liquid fertilizers, micronutrients, biological organisms, oils, or solvents.

[0214] These formulations can be prepared, for example, by mixing the active ingredient with formulation aids to obtain a composition in the form of a finely divided solid, granules, solution, dispersion, or emulsion. These active ingredients can also be formulated together with other auxiliaries (such as finely divided solids, mineral oils, oils of plant or animal origin, modified oils of plant or animal origin, organic solvents, water, surface-active substances, or combinations thereof).

[0215] These active ingredients can also be incorporated into very fine microcapsules. The microcapsules contain the active ingredient in a porous carrier. This enables the active ingredient to be released into the environment in a controlled amount (for example, slowly). Microcapsules generally have a diameter from 0.1 to 500 micrometers. The amount of active ingredient they contain is about from 25% to 95% by weight of the weight of the capsule. These active ingredients can be in the form of a solid mass, in the form of fine particles in a solid or liquid dispersion, or in a form suitable for a solution. The encapsulating membrane can contain, for example, natural or synthetic rubbers, celluloses, styrene / butadiene copolymers, polyacrylonitriles, polyacrylates, polyesters, polyamides, polyureas, polyurethanes, or chemically modified polymers, as well as starch xanthate, or other polymers known to those skilled in the art. Alternatively, very fine microcapsules can be formed in which the active ingredient is contained in the solid matrix of the base material in the form of finely divided particles, but these microcapsules are not themselves encapsulated.

[0216] The formulation aids suitable for preparing the composition according to the present invention are known per se. As liquid carriers, the following can be used: water, toluene, xylene, petroleum ether, vegetable oil, acetone, methyl ethyl ketone, cyclohexanone, acid anhydride, acetonitrile, acetophenone, amyl acetate, 2-butanone, butylene carbonate, chlorobenzene, cyclohexane, cyclohexanol, alkyl acetate, diacetone alcohol, 1,2-dichloropropane, diethanolamine, p-diethylbenzene, diethylene glycol, diethylene glycol rosin acid ester, diethylene glycol butyl ether, diethylene glycol ethyl ether, diethylene glycol methyl ether, N,N-dimethylformamide, dimethyl sulfoxide, 1,4-dioxane, dipropylene glycol, dipropylene glycol methyl ether, dipropylene glycol dibenzoate, dipropylene glycol, alkyl pyrrolidone, ethyl acetate, 2-ethylhexanol, ethylene carbonate, 1,1,1-trichloroethane, 2-heptanone, α-pinene, d-limonene, ethyl lactate, ethylene glycol, ethylene glycol butyl ether, ethylene glycol methyl ether, γ-butyrolactone, glycerol, glycerol acetate, glycerol diacetate, glycerol triacetate, hexadecane, hexanediol, isoamyl acetate, isobornyl acetate, isooctane, isophorone, cumene, isopropyl myristate, lactic acid, laurylamine, isopropylidene acetone, methoxypropanol, methyl isoamyl ketone, methyl isobutyl ketone, methyl laurate, methyl octanoate, methyl oleate, dichloromethane, m-xylene, n-hexane, n-octylamine, stearic acid, octylamine acetate, oleic acid, oleylamine, o-xylene, phenol, polyethylene glycol, propionic acid, propyl lactate, propylene carbonate, propylene glycol, propylene glycol methyl ether, p-xylene, toluene, triethyl phosphate, triethylene glycol, xylene sulfonic acid, paraffin wax, mineral oil, trichloroethylene, perchloroethylene, ethyl acetate, amyl acetate, butyl acetate, propylene glycol methyl ether, diethylene glycol methyl ether, methanol, ethanol, isopropyl alcohol and higher molecular weight alcohols such as pentanol, tetrahydrofurfuryl alcohol, hexanol, octanol, ethylene glycol, propylene glycol, glycerol, N-methyl-2-pyrrolidone, etc.

[0217] Suitable solid carriers are, for example, talc, titanium dioxide, pyrophyllite clay, silica, attapulgite clay, diatomaceous earth, limestone, calcium carbonate, bentonite, calcium montmorillonite, cottonseed hulls, wheat flour, soybean flour, pumice, wood flour, ground walnut shells, lignin and similar substances.

[0218] Many surface active substances can be advantageously used in both solid and liquid formulations, especially those which can be diluted by a carrier before use. The surface active substances can be anionic, cationic, nonionic or polymeric and they can be used as emulsifiers, wetting agents or suspending agents or for other purposes. Typical surface active substances include, for example, salts of alkyl sulfates, such as diethanolammonium lauryl sulfate; salts of alkyl aryl sulfonates, such as calcium dodecylbenzenesulfonate; alkylphenol / alkylene oxide adducts, such as ethoxylated nonylphenol; alcohol / alkylene oxide adducts, such as ethoxylated tridecanol; soaps, such as sodium stearate; salts of alkylnaphthalenesulfonates, such as sodium dibutylnaphthalenesulfonate; salts of dialkyl esters of sulfosuccinic acid, such as sodium bis(2-ethylhexyl) sulfosuccinate; sorbitan esters, such as sorbitan oleate; quaternary ammonium, such as dodecyltrimethylammonium chloride; polyethylene glycol esters of fatty acids, such as polyethylene glycol stearate; block copolymers of ethylene oxide and propylene oxide; and salts of monoalkyl and dialkyl phosphates; and also other substances, for example as described in: McCutcheon's Detergents and Emulsifiers Annual, MC Publishing Corp., Ridgewood, New Jersey (1981).

[0219] Additional adjuvants which can be used in pesticidal formulations include crystallization inhibitors, viscosity modifiers, suspending agents, dyes, antioxidants, foaming agents, light absorbers, mixing aids, defoamers, complexing agents, substances for neutralizing or altering the pH and buffers, corrosion inhibitors, fragrances, wetting agents, absorption enhancers, micronutrients, plasticizers, glidants, lubricants, dispersants, thickeners, antifreeze agents, microbicides, and liquid and solid fertilizers.

[0220] The compositions according to the invention can include an additive which comprises an oil of vegetable or animal origin, a mineral oil, an alkyl ester of such an oil or a mixture of such an oil with an oil derivative. The amount of the oil additive in the composition according to the invention is generally from 0.01% to 10% based on the mixture to be applied. For example, the oil additive can be added to the spray tank at the desired concentration after the spray mixture has been prepared. Preferred oil additives include mineral oil or oils of vegetable origin, such as rapeseed oil, olive oil or sunflower oil; emulsified vegetable oils; alkyl esters of oils of vegetable origin, such as methyl derivatives; or oils of animal origin, such as fish oil or tallow. Preferred oil additives include alkyl esters of C8-C 22 fatty acids, especially C 12 -C 18Methyl derivatives of fatty acids, such as methyl esters of lauric acid, palmitic acid and oleic acid (methyl laurate, methyl palmitate and methyl oleate, respectively). Many oil derivatives are known from Compendium of Herbicide Adjuvants, 10th Edition, Southern Illinois University, 2010.

[0221] The compositions according to the invention generally comprise from 0.1% to 99% by weight, in particular from 0.1% to 95% by weight, of the compound according to the invention and from 1% to 99.9% by weight of a formulation adjuvant, which preferably comprises from 0 to 25% by weight of a surface-active substance. Commercial products may preferably be formulated as concentrates, and the end user will generally use a diluted formulation.

[0222] The application rates vary within a wide range and depend on the nature of the soil, the method of application, the crop plant, the pest to be controlled, the prevailing climatic conditions, and other factors governed by the method of application, the time of application and the target crop. Generally speaking, the compounds may be applied at a rate of from 1 l / ha to 2000 l / ha, in particular from 10 l / ha to 1000 l / ha.

[0223] Preferred formulations may have the following composition (% by weight):

[0224] Emulsifiable concentrate :

[0225] Active ingredient: 1% to 95%, preferably 60% to 90%

[0226] Surfactant: 1% to 30%, preferably 5% to 20%

[0227] Liquid carrier: 1% to 80%, preferably 1% to 35%

[0228] Dust :

[0229] Active ingredient: 0.1% to 10%, preferably 0.1% to 5%

[0230] Solid carrier: 99.9% to 90%, preferably 99.9% to 99%

[0231] Suspension concentrate:

[0232] Active ingredient: 5% to 75%, preferably 10% to 50%

[0233] Water: 94% to 24%, preferably 88% to 30%

[0234] Surfactant: 1% to 40%, preferably 2% to 30%

[0235] Wettable powder :

[0236] Active ingredient: 0.5% to 90%, preferably 1% to 80%

[0237] Surfactant: 0.5% to 20%, preferably 1% to 15%

[0238] Solid carrier: 5% to 95%, preferably 15% to 90%

[0239] Granules:

[0240] Active ingredient: 0.1% to 30%, preferably 0.1% to 15%

[0241] Solid carrier: 99.5% to 70%, preferably 97% to 85%

[0242] The following examples further illustrate (but do not limit) the present invention.

[0243]

[0244] The combination was thoroughly mixed with these auxiliaries and the mixture was thoroughly ground in a suitable grinder to obtain a wettable powder which could be diluted with water to give a suspension of the desired concentration.

[0245] <![CDATA Powder for dry seed treatment > a) b) c) Active ingredient 25％ 50％ 75％ Light mineral oil 5％ 5％ 5％ Highly disperse silicic acid 5％ 5％ - Kaolin 65％ 40％ - Talc - 20％

[0246] The combination was thoroughly mixed with the auxiliaries and the mixture was thoroughly ground in a suitable grinder to obtain a powder which could be used directly for seed treatment.

[0247]

[0248] An emulsion having any desired dilution which can be used in plant protection can be obtained by diluting this concentrate with water.

[0249] <![CDATA Dust > a) b) c) Active ingredient 5％ 6％ 4％ Talc 95％ - - Kaolin - 94％ - Mineral filler - - 96％

[0250] A ready-to-use dusting powder was obtained by mixing the combination with a carrier and grinding the mixture in a suitable grinder. Such a powder can also be used for dry dressing of seeds.

[0251] <![CDATA Extruder granules > Active ingredient 15％ Sodium lignosulfonate 2％ Carboxymethyl cellulose 1％ Kaolin 82％

[0252] The combination was mixed and ground with these auxiliaries and the mixture was moistened with water. The mixture was extruded and then dried in an air stream.

[0253] <![CDATA Coated granules > Active ingredient 8％ Polyethylene glycol (molecular weight 200) 3％ Kaolin 89％

[0254] The finely ground combination is uniformly applied to kaolin moistened with polyethylene glycol in a mixer. In this way, dust-free coated granules are obtained.

[0255] Suspension concentrate

[0256] Active ingredient 40％ Propylene glycol 10％ Nonylphenol polyethylene glycol ether (15 mol ethylene oxide) 6％ Sodium lignosulfonate 10％ Carboxymethyl cellulose 1％ Silicone oil (in the form of a 75% emulsion in water) 1％ Water 32％

[0257] The finely ground combination is intimately mixed with adjuvants to give a suspension concentrate from which suspensions of any desired dilution can be obtained by dilution with water. Using such dilutions, living plants together with plant propagation material can be treated and protected against microbial infestation by spraying, watering or dipping.

[0258] Flowable concentrate for seed treatment

[0259]

[0260] The finely ground combination is intimately mixed with adjuvants to give a suspension concentrate from which suspensions of any desired dilution can be obtained by dilution with water. Using such dilutions, living plants together with plant propagation material can be treated and protected against microbial infestation by spraying, watering or dipping.

[0261] Sustained release capsule suspension

[0262] 28 parts of the combination are mixed with 2 parts of an aromatic solvent and 7 parts of a toluene diisocyanate / polymethylene-polyphenyl isocyanate-mixture (8:1). This mixture is emulsified in a mixture of 1.2 parts of polyvinyl alcohol, 0.05 part of an antifoaming agent and 51.6 parts of water until the desired particle size is reached. 2.8 parts of a 1,6-hexanediamine mixture in 5.3 parts of water are added to this emulsion. The mixture is stirred until the polymerization reaction is complete. The obtained capsule suspension is stabilized by adding 0.25 part of a thickener and 3 parts of a dispersant. The capsule suspension formulation contains 28% of the active ingredient. The diameter of the medium capsules is 8 - 15 microns. The resulting formulation is applied as an aqueous suspension in a device suitable for this purpose to the seeds.

[0263] Formulation types include emulsion concentrates (EC), suspension concentrates (SC), suspoemulsions (SE), capsule suspensions (CS), water-dispersible granules (WG), emulsifiable granules (EG), emulsions, water-in-oil emulsions (EO), oil-in-water emulsions (EW), microemulsions (ME), oil dispersions (OD), oil suspensions (OF), oil-soluble solutions (OL), soluble concentrates (SL), ultra-low volume suspensions (SU), ultra-low volume solutions (UL), technical material (TK), dispersible concentrates (DC), wettable powders (WP), soluble granules (SG), or any technically feasible formulation in combination with agriculturally acceptable adjuvants.

[0264] Preparation examples:

[0265] LCMS method:

[0266] Method 1:

[0267] Spectra were recorded on a mass spectrometer (SQD, SQDII or QDA single quadrupole mass spectrometer) from Waters Corporation, equipped with an electrospray source (polarity: positive and negative ions), capillary voltage: 0.8 - 3.00 kV, cone voltage: 5 - 30 V, source temperature: 120 °C - 150 °C, desolvation temperature: 350 °C - 600 °C, cone gas flow: 50 - 150 l / h, desolvation gas flow: 650 - 1000 l / h, mass range: 110 to 950 Da and an Acquity UPLC from Waters Corporation: binary pump, heated column compartment, diode array detector and ELSD. Column: Waters UPLC HSS T3, 1.8 μm, 30 x 2.1 mm, temperature: 60 °C, DAD wavelength range (nm): 210 to 400, run time: 1.5 min; solvents: A = water + 5% MeOH + 0.05% HCOOH, B = acetonitrile + 0.05% HCOOH; flow rate (ml / min) 0.85, gradient: 10% B isocratic for 0.2 min, then 10% - 100% B in 1.0 min, 100% B isocratic for 0.2 min, 100% - 10% B in 0.05 min, 10% B isocratic for 0.05 min.

[0268] The following abbreviations were used in the experimental descriptions below: s = singlet, d = doublet, t = triplet, q = quartet, m = multiplet, RT = retention time, min = minute.

[0269] Example P1: 1-[5-cyano-2-(trifluoromethyl)-6-[4-(trifluoromethyl)phenyl]pyridine-3-carbonyl]-N-ethyl -N-methyl-piperidine-4-sulfonamide (Compound P.4):

[0270]

[0271] Step 1: Ethyl 5-cyano-6-hydroxy-2-(trifluoromethyl)pyridine-3-carboxylate

[0272]

[0273] A solution of sodium ethoxide (1.1 eq) in ethanol (20% w / w) was slowly added to a suspension of 2-cyano-acetamide (5.9 g, 70.2 mmol, 1 eq) at 4 °C, and the mixture was stirred for 15 minutes. Then a solution of ethyl 2-(ethoxymethylene)-4,4,4-trifluoro-3-oxo-butanoate (17 g, 70.1 mmol) in 34 ml of ethanol was added under ice-cooling. The reaction mixture was stirred for 16 h and allowed to reach room temperature. Then the reaction mixture was poured into ice-cold 1 N hydrochloric acid solution. The resulting mixture was diluted with ice-cold water and stirred for 20 minutes. The precipitate was filtered, washed twice with ice-cold water and dried. 12.4 g of ethyl 5-cyano-6-hydroxy-2-(trifluoromethyl)pyridine-3-carboxylate was obtained with a purity higher than 95% as determined by quantitative NMR. 1 1H-NMR [ppm], in CDCl3: 1.29 (t, 3H), 4.29 (q, 2H), 8.27 (s, 1H).

[0274] Step 2: Ethyl 6-chloro-5-cyano-2-(trifluoromethyl)pyridine-3-carboxylate

[0275]

[0276] Ethyl 5-cyano-6-hydroxy-2-(trifluoromethyl)pyridine-3-carboxylate (7.00 g, 26.9 mmol) was suspended in dichloromethane (100 mL) and DMF (1 mL), and the mixture was cooled to 0 °C, followed by the addition of oxalyl chloride (6.83 mL, 80.7 mmol). The reaction mixture was refluxed for 6 h, cooled to room temperature, diluted with saturated sodium carbonate solution, extracted with dichloromethane (3 × 250 mL), dried over Na2SO4, concentrated under reduced pressure and purified by chromatography (hexane:ethyl acetate 5:1) to give 5.12 g of ethyl 6-chloro-5-cyano-2-(trifluoromethyl)pyridine-3-carboxylate as a white solid. 1 1H-NMR [ppm], in CDCl3: 1.42 (t, 3H), 4.46 (q, 2H), 8.45 (s, 1H).

[0277] Step 3: Ethyl 5-cyano-2-(trifluoromethyl)-6-[4-(trifluoromethyl)phenyl]pyridine-3-carboxylate

[0278]

[0279] Under argon, potassium carbonate (1.98 g, 14.4 mmol), [4-(trifluoromethyl)phenyl]boronic acid (2.73 g, 14.4 mmol) and tetrakis(triphenylphosphine)palladium(0) (0.855 g, 0.718 mmol, 0.05 equiv) were added to a solution of ethyl 6-chloro-5-cyano-2-(trifluoromethyl)pyridine-3-carboxylate (4.00 g, 14.4 mmol) in toluene (28.7 mL). The suspension was heated under reflux for 4 h. The reaction mixture was diluted with water and saturated ammonium chloride solution and extracted three times with ethyl acetate. The combined organic layers were extracted with water and brine, dried over sodium sulfate and concentrated. The residue was purified by silica gel column chromatography to give 4.43 g of ethyl 5-cyano-2-(trifluoromethyl)-6-[4-(trifluoromethyl)phenyl]pyridine-3-carboxylate as a white solid. 1 1H-NMR [ppm], in CDCl3: 1.45 (t, 3H), 4.52 (q, 2H), 7.86 (d, 2H), 8.22 (d, 2H), 8.61 (s, 1H); LC-MS (method 1): RT = 1.19 min; [M+H] + = 389.

[0280] Step 4: 5-Cyano-2-(trifluoromethyl)-6-[4-(trifluoromethyl)phenyl]pyridine-3-carboxylic acid

[0281]

[0282] Lithium hydroxide monohydrate (0.75 g, 18 mmol, 4 equiv) was added to a solution of ethyl 5-cyano-2-(trifluoromethyl)-6-[4-(trifluoromethyl)phenyl]pyridine-3-carboxylate (1.70 g, 4.4 mmol) in tetrahydrofuran (11 mL) and water (5.3 mL). The reaction mixture was stirred at room temperature for 2 h. Then the reaction mixture was diluted with ethyl acetate and 2N hydrochloric acid and extracted three times with ethyl acetate. The combined organic layers were extracted with water and brine, dried over sodium sulfate and concentrated under reduced pressure to give 1.47 g of 5-cyano-2-(trifluoromethyl)-6-[4-(trifluoromethyl)phenyl]pyridine-3-carboxylic acid. 1 1H-NMR [ppm], in DMSO-d6: 8.02 (d, 2H), 8.14 (d, 2H), 8.99 (s, 1H), 14.3 (broad s, 1H); LC-MS (method 1): RT = 0.95 min; [M+H] + = 361.

[0283] Step 5: tert-Butyl 4-[ethyl(methyl)sulfamoyl]piperidine-1-carboxylate

[0284]

[0285] To a solution of commercially available tert-butyl 4-chlorosulfonylpiperidine-1-carboxylate (10.0 g, 33.5 mmol) in tetrahydrofuran (100 mL) was added N-ethyl-methylamine (8.9 mL, 100.4 mmol, 3 equiv). The reaction was stirred at room temperature for 12 h. The reaction mixture was poured into water and extracted with ethyl acetate. The combined organic layers were washed with water and brine, dried over sodium sulfate and concentrated under reduced pressure. The residue was purified by combiflash (30%-60% EtOac / cyclohexane) to afford 7.6 g of tert-butyl 4-[ethyl(methyl)aminosulfonyl]piperidine-1-carboxylate. 1 1H-NMR [ppm], in CDCl3: 1.21 (t, 3H), 1.45 (s, 9H), 1.62 - 1.78 (m, 2H), 2.01 (broad d, 2H), 2.60 - 2.78 (m, 2H), 2.90 (s, 3H), 2.99 - 3.08 (m, 1H), 3.29 (q, 2H), 4.24 (broad s, 2H).

[0286] Step 6: N-Ethyl-N-methylpiperidin-1-ium-4-sulfonamide chloride

[0287]

[0288] tert-Butyl 4-[ethyl(methyl)aminosulfonyl]piperidine-1-carboxylate (7.6 g, 24 mmol) was dissolved in methanol (76 mL) and a solution of hydrogen chloride (94 mmol, 4 equiv) in methanol (3 mol / L) was added. The reaction mixture was stirred at room temperature for 12 h and then the solvent was evaporated. The crude product was triturated with tert-butyl methyl ether to give 5.7 g of N-ethyl-N-methylpiperidin-1-ium-4-sulfonamide chloride. 1 1H-NMR [ppm], in DMSO-d6: 1.22 (t, 3H), 1.85 - 1.98 (m, 2H), 2.24 (broad d, 2H), 2.85 (s, 3H), 2.94 - 3.05 (m, 2H), 3.24 (q, 2H), 3.46 - 3.63 (m, 3H).

[0289] Step 7: 1-[5-Cyano-2-(trifluoromethyl)-6-[4-(trifluoromethyl)phenyl]pyridine-3-carbonyl]-N-ethyl-N-methylpiperidine-4-sulfonamide (Compound P.4)

[0290]

[0291] To a solution of 5-cyano-2-(trifluoromethyl)-6-[4-(trifluoromethyl)phenyl]pyridine-3-carboxylic acid (200 mg, 0.555 mmol) in dimethylformamide (5 mL) was added N-ethyl-N-methyl-piperidin-1-ium-4-sulfonamide chloride (202 mg, 0.833 mmol, 1.50 equiv), followed by addition of HATU coupling reagent (239 mg, 0.611 mmol, 1.1 equiv) and N,N-diisopropyl-ethylamine (0.34 mL, 2.00 mmol, 3.6 equiv). The reaction mixture was stirred at room temperature for three hours. The reaction was quenched with NaHCO3 solution and extracted three times with ethyl acetate. The combined organic layers were dried over sodium sulfate and concentrated under reduced pressure. The residue was purified by Combiflash to afford 150 mg of 1-[5-cyano-2-(trifluoromethyl)-6-[4-(trifluoromethyl)phenyl]pyridine-3-carbonyl]-N-ethyl-N-methyl-piperidine-4-sulfonamide as a white foam. 1 1H-NMR [ppm], in CDCl3: 1.22 - 1.28 (m, 3H), 1.71 - 2.03 (m, 2H), 2.06 - 2.16 (m, 1H), 2.18 - 2.37 (m, 1H), 2.86 - 3.06 (m, 1H), 2.94 (s, 3H), 3.12 - 3.24 (m, 2H), 3.29 - 3.39 (m, 2H), 3.56 (t, 1H), 4.86 (dd, 1H), 7.87 (d, 2H), 8.19 (d, 2H), 8.12 and 8.22 (2s, 1H). LC-MS (method 1): RT = 1.09 min; [M+H] + = 549.

[0292] Example P2: 1-[5-cyano-2-(trifluoromethyl)-6-[4-(trifluoromethyl)phenyl]pyridine-3-carbonyl]-N-ethyl -piperidine-4-sulfonamide (Compound P.6):

[0293]

[0294] Step 1: tert-Butyl 4-(ethylsulfamoyl)piperidine-1-carboxylate

[0295]

[0296] To a solution of commercially available tert-butyl 4-chlorosulfonylpiperidine-1-carboxylate (1.5 g, 5.0 mmol) in tetrahydrofuran (15 mL) was added a solution of N-ethyl-amine in water (ca. 12 mol / L, 1.6 mL, 25 mmol, 5 equiv). The reaction was stirred at room temperature for 2 hours. The reaction mixture was concentrated to dryness under reduced pressure. The residue was triturated with cold water to afford 1.4 g of tert-butyl 4-(ethylsulfamoyl)piperidine-1-carboxylate. 11H-NMR [ppm], in DMSO-d6: 1.07 (t, 3H), 1.40 (s, 9H), 1.36 - 1.45 (m, 2H), 1.94 (broad d, 2H), 2.62 - 2.9 (broad s, 2H), 2.91 - 3.01 (m, 2H), 3.10 - 3.24 (m, 1H), 3.95 - 4.08 (broad d, 2H), 7.09 (t, 1H).

[0297] Step 2: N-Ethyl-piperidin-1-ium-4-sulfonamide chloride

[0298]

[0299] Dissolve tert-butyl 4-(ethylsulfamoyl)piperidine-1-carboxylate (1.4 g, 4.5 mmol) in methanol (14 mL) and add a solution of hydrogen chloride (18 mmol, 4 equiv) in methanol (3 mol / L). Stir the reaction mixture at room temperature for 12 h and then evaporate the solvent. Triturate the crude product with acetonitrile to give 1.1 g of N-ethyl-piperidin-1-ium-4-sulfonamide chloride. 1 1H-NMR [ppm], in DMSO-d6: 1.06 (t, 3H), 1.75 - 1.90 (m, 2H), 2.24 (broad d, 2H), 2.91 - 3.02 (m, 2H), 3.03 (q, 2H), 3.39 - 3.53 (m, 3H).

[0300] Step 3: 1-[5-Cyano-2-(trifluoromethyl)-6-[4-(trifluoromethyl)phenyl]pyridine-3-carbonyl]-N-ethyl-piperidine-4-sulfonamide (Compound P.6)

[0301]

[0302] To a solution of 5-cyano-2-(trifluoromethyl)-6-[4-(trifluoromethyl)phenyl]pyridine-3-carboxylic acid (200 mg, 0.555 mmol) in dimethylformamide (5 mL) was added N-ethyl-piperidin-1-ium-4-sulfonamide chloride (191 mg, 0.833 mmol, 1.50 equiv), followed by addition of HATU coupling reagent (239 mg, 0.611 mmol, 1.1 equiv) and N,N-diisopropyl-ethylamine (0.34 mL, 2.00 mmol, 3.6 equiv). The reaction mixture was stirred at room temperature for three hours. The reaction was quenched with NaHCO3 solution and extracted three times with ethyl acetate. The combined organic layers were dried over sodium sulfate and concentrated under reduced pressure. The residue was purified by Combiflash to afford 145 mg of 1-[5-cyano-2-(trifluoromethyl)-6-[4-(trifluoromethyl)phenyl]pyridine-3-carbonyl]-N-ethyl-piperidine-4-sulfonamide as a white foam. 1 1H-NMR [ppm], in DMSO-d6: 1.04 - 1.13 (m, 3H), 1.35 - 1.58 (m, 1H), 1.62 - 1.81 (m, 1H), 1.81 - 1.94 (broad t, 1H), 2.06 - 2.18 (m, 1H), 2.85 - 3.42 (m, 5H), 3.52 - 3.68 (m, 1H), 3.61 (broad t, 1H), 7.14 (t, 1H), 8.02 (d, 2H), 8.14 (d, 2H), 8.88 and 9.04 (2s, 1H). LC-MS (method 1): RT = 1.04 min; [M+H] + = 535.

[0303] Table P: Compounds of formula (I-a)

[0304]

[0305] The compounds in Table P can be prepared by the methods described in the above examples or similar methods. The following abbreviations are used in the table below: RT = retention time, min = minute.

[0306] Table P:

[0307]

[0308] By adding other ingredients having insecticidal, acaricidal and / or fungicidal activity, the activity of the compositions according to the invention can be significantly broadened and is suitable for general situations. Mixtures of the compounds of formula (I) with other ingredients having insecticidal, acaricidal and / or fungicidal activity may also have additional unexpected advantages, which may also be described in a broader sense as synergistic activity. For example, better tolerance of plants, reduced phytotoxicity, insects can be controlled at their different developmental stages, or better behavior during their production (e.g., during grinding or mixing, during their storage or during their use).

[0309] Here, the active ingredients suitable for addition are representatives of the active ingredients of the following classes, for example: organophosphorus compounds, nitrophenol derivatives, thioureas, juvenile hormones, formamidines, benzophenone derivatives, ureas, pyrrole derivatives, carbamates, pyrethroids, chlorinated hydrocarbons, acyl ureas, pyridylmethyleneamino derivatives, macrolides, neonicotinoids and Bacillus thuringiensis preparations.

[0310] The following mixtures of the compounds of formula (I) with the active substances in a weight ratio of 1:1 are preferred (the abbreviation "TX" means "a compound selected from the compounds defined in Tables 1 to 7 and Table P"):

[0311] (7E,9Z)-Dodeca-7,9-dien-1-yl acetate + TX, (9Z,11E)-Tetradeca-9,11-dien-1-yl acetate + TX, (9Z,12E)-Tetradeca-9,12-dien-1-yl acetate + TX, (E)-6-Methylhept-2-en-4-ol + TX, (E)-Dec-5-en-1-yl acetate and (E)-Dec-5-en-1-ol + TX, (E)-Tridec-4-en-1-yl acetate + TX, (E,Z)-Tetradeca-4,10-dien-1-yl acetate + TX, (Z)-Dodec-7-en-1-yl acetate + TX, (Z)-Hexadec-11-en-1-yl acetate + TX, (Z)-Hexadec-11-enal + TX, (Z)-Hexadec-13-en-11-yn-1-yl acetate + TX, (Z)-Eicos-13-en-10-one + TX, (Z)-Tetradec-7-en-1-al + TX, (Z)-Tetradec-9-en-1-ol + TX, (Z)-Tetradec-9-en-1-yl acetate + TX, 1,2-Dibromo-3-chloropropane + TX, 1,2-Dichloropropane + TX, 1,2-Dichloropropane and 1,3-Dichloropropene + TX, 1,3-Dichloropropene + TX, 14-Methyloctadec-1-ene + TX, 1-Hydroxy-1H-pyridine-2-thione + TX, 2-(Octylthio)ethanol + TX, 2-Chlorophenyl N-methylcarbamate (CPMC) + TX, 3-(4-Chlorophenyl)-5-methylrhodanine + TX, 3,4-Dichlorotetrahydrothiophene 1,1-dioxide + TX, 4-(Quinoxalin-2-ylamino)benzenesulfonamide + TX, 4-Methylnon-5-ol and 4-Methylnon-5-one + TX, 5-Methyl-6-thioxo-1,3,5-thiadiazin-3-ylacetic acid + TX, 6-Isopentenylaminopurine + TX, 8-Hydroxyquinoline sulfate + TX, Abamectin + TX, Acequinocyl + TX, Acetamiprid + TX, Acemetacin + TX, Alphamethrin + TX, Acynonapyr + TX, Adoxophyes orana GV + TX, Alanapyridines + TX, Afoxolaner + TX, Agrobacterium radiobacter + TX, AKD-3088 + TX, Aldicarb + TX, Aldicarb sulfone + TX, Allethrin + TX, Alpha-cypermethrin + TX, Beta-cypermethrin + TX, Alpha-multistriatin + TX, Amblyseius species + TX, Amdro + TX, Amino acids + TX, Aminocarb + TX, Anagrapha falcifera NPV + TX, Anastatus atomarius + TX, Aphytis proclia + TX, Aphidius gifuensis + TX, Aphidoletes aphidimyza + TX, Azamethiphos + TX, Autographa californica NPV + TX, AZ 60541 + TX, Azadirachtin + TX, Azocyclotin + TX, Bacillus aizawai + TX,Bacillus chitinosporus AQ746 (NRRL accession number B-21618) + TX, Bacillus firmus + TX, Bacillus sp. Kurstaki + TX, Bacillus mycoides AQ726 (NRRL accession number B-21664) + TX, Bacillus pumilus (NRRL accession number B-30087) + TX, Bacillus pumilus AQ717 (NRRL accession number B-21662) + TX, Bacillus sp. AQ175 (ATCC accession number 55608) + TX, Bacillus sp. AQ177 (ATCC accession number 55609) + TX, Bacillus sp. AQ178 (ATCC accession number 53522) + TX, Bacillus sphaericus + TX, Bacillus subtilis AQ153 (ATCC accession number 55614) + TX, Bacillus subtilis AQ30002 (NRRL accession number B-50421) + TX, Bacillus subtilis AQ30004 (NRRL accession number B-50455) + TX, Bacillus subtilis AQ713 (NRRL accession number B-21661) + TX, Bacillus subtilis AQ743 (NRRL accession number B-21665) + TX, Bacillus subtilis not specified + TX, Bacillus thuringiensis AQ52 (NRRL accession number B-21619) + TX, Bacillus thuringiensis BD#32 (NRRL accession number B-21530) + TX, Bacillus thuringiensis + TX, Bacillus thuringiensis subsp. aizawai + TX, Bacillus thuringiensis subsp. israelensis + TX, Bacillus thuringiensis subsp. japonensis + TX, Bacillus thuringiensis subsp. kurstaki + TX, Bacillus thuringiensis subsp. tenebrionis + TX, Bacillus thuringiensis subsp. kurstaki BMP 123 + TX, Beauveria bassiana + TX, Beauveria brongniartii + TX, benclothiaz + TX, benomyl + TX, bensultap + TX, benzoximate + TX, bixafen + TX, beta-cyfluthrin + TX, beta-cypermethrin + TX, binapacryl + TX, bifenazate + TX, bifenthrin + TX, binapacryl + TX, allethrin + TX, bioallethrin + TX, bis(tributyltin) oxide + TX, bis(aziridinyl) methylaminophosphine sulfide (bisazir) + TX, bistrifluron + TX, western pine beetle aggregation pheromone (brevicomin) + TX, broflanilide + TX, brofluthrinate + TX, bromoacetamide + TX, bromophos-ethyl + TX, bronopol + TX, buprofezin + TX, busulfan + TX, butocarboxim + TX, butopyronoxyl + TX, butoxy(polypropylene glycol) + TX, butylpyridaben + TX, cadusafos + TX, calcium arsenate + TX, carbaryl + TX, carbofuran + TX, carbon disulfide + TX, carbosulfan + TX, cartap + TX,CAS No.: 1594624-87-9 + TX, CAS No.: 1922957-47-8 + TX, CAS No.: 1255091-74-7 + TX, CAS No.: 1365070-72-9 + TX, CAS No.: 1445683-71-5 + TX, CAS No.: 1445684-82-1 + TX, CAS No.: 1594626-19-3 + TX, CAS No.: 1594637-65-6 + TX, CAS No.: 1632218-00-8 + TX, CAS No.: 1808115-49-2 + TX, CAS No.: 1922957-45-6 + TX, CAS No.: 1922957-46-7 + TX, CAS No.: 1922957-48-9 + TX, CAS No.: 1956329-03-5 + TX, CAS No.: 1990457-52-7 + TX, CAS No.: 1990457-55-0 + TX, CAS No.: 1990457-57-2 + TX, CAS No.: 1990457-66-3 + TX, CAS No.: 1990457-77-6 + TX, CAS No.: 1990457-85-6 + TX, CAS No.: 2032403-97-5 + TX, CAS No.: 2044701-44-0 + TX, CAS No.: 2095470-94-1 + TX, CAS No.: 2128706-05-6 + TX, CAS No.: 2133042-31-4 + TX, CAS No.: 2133042-44-9 + TX, CAS No.: 2171099-09-3 + TX, CAS No.: 2220132-55-6 + TX, CAS No.: 2368920-61-8 + TX, CAS No.: 2377084-09-6 + TX, CAS No.: 2396747-83-2 + TX, CAS No.: 2408220-91-5 + TX, CAS No.: 2408220-94-8 + TX, CAS No.: 2415706-16-8 + TX, CAS No.: 2615135-05-0 + TX, CAS No.: 2719848-60-7 + TX, CAS No.: RNA (Colorado potato beetle - specific recombinant double - stranded interfering GS2) + TX, Chlorantraniliprole + TX, Chlordane + TX, Chlorfenapyr + TX, Chloropicrin + TX, Permethrin + TX, Chlorpyrifos + TX, Tebufenozide + TX, Chrysoperla carnea + TX, Clenpirin + TX, Cloethocarb + TX, Clothianidin + TX, Codlelure + TX, Codlemone + TX, Cupric acetoarsenite + TX, Copper caprylate + TXCopper hydroxide + TX, copper sulfate + TX, cresol + TX, crufomate + TX, Cryptolaemus montrouzieri + TX, cuelure + TX, cyanofenphos + TX, cyantraniliprole + TX, cybutryne + TX, cyclaniliprole + TX, cyclobutrifluram + TX, pyrethroid + TX, epoxyfenidin + TX, Cydia pomonella GV + TX, cyenopyrafen + TX, cyetpyrafen + TX, flufenoxuron + TX, cyhalothrin + TX, cypermethrin + TX, cyphenothrin + TX, cyproflanilide + TX, cyromazine + TX, cytokinins + TX, Dacnusa sibirica + TX, dazomet + TX, DBCP + TX, DCIP + TX, deltamethrin + TX, dicofol + TX, dialifos + TX, diamidafos + TX, dibrom + TX, dibutyl adipate + TX, dibutylphthalate + TX, dibutyl succinate + TX, dichlofenthion + TX, dichlone + TX, dichlorophen + TX, dicliphos + TX, dicloromezotiaz + TX, diethyltoluamide + TX, diflubenzuron + TX, Diglyphus isaea + TX, dimatif + TX, dimethoate + TX, dimethylcarbate + TX, dimethyl phthalate + TX, dimpropyridaz + TX, diamycin + TX, dinocap + TX, dinotefuran + TX, dioxabenzofos + TX, dipyrithione + TX, disparlure + TX, D-limonene + TX, dodec-8-en-1-yl acetate + TX, dodec-9-en-1-yl acetate + TX, dodec-8,10-dien-1-yl acetate + TX, dodicin + TX, dominicalure + TX,Doramectin + TX, Emamectin + TX, Emamectin Benzoate + TX, d - Transfluthrin + TX, Encarsia + TX, Endothal + TX, Endrin + TX, Eprinomectin + TX, ε - Methoxyfluthrin + TX, ε - Methoxybenzfluthrin + TX, Eretmocerus eremicus + TX, Esfenvalerate + TX, Ethion + TX, Ethiprole + TX, Ethoprophos + TX, Ethyl 4 - methylcaprylate + TX, Ethylhexanediol + TX, Ethylene Dibromide + TX, Etofenprox + TX, Etoxazole + TX, Etpyrafen + TX, Eugenol + TX, Seaweed extract and fermentation products derived from glycosyl, Seaweed extract and fermentation products derived from glycosyl containing urea, Seaweed extract and fermentation plant products, Seaweed extract and fermentation plant products (containing phytohormones + TX, vitamins + TX, EDTA - chelated copper + TX, zinc + TX and iron + TX), Famphur + TX, Fenaminosulf + TX, Fenamiphos + TX, Fenazaquin + TX, Flucythrinate + TX, Fenitrothion + TX, Fenmezoditiaz + TX, Fenobucarb + TX, BPMC + TX, Phenoxycarb + TX, Fenpropathrin + TX, Fenpyrad + TX, Fenpyroximate + TX, Fensulfothion + TX, Fenthion + TX, Fentin + TX, Fentin acetate + TX, Fenvalerate + TX, Ferric Phosphate + TX, Fipronil + TX, Flometoquin + TX, Flonicamid + TX, Flufenerim + TX, Fluazaindolizine + TX, Flonicamid + TX, Flubendiamide + TX, Flufenerim + TX, Flubendiamide + TX, Flucitrinate + TX, Flucycloxuron + TX, Fluvalinate + TX, Fluensulfone + TX, Flumioxazin [318290 - 98 - 1]+TX, Flufenerim + TX, Tefluthrin + TX, Butene - fipronil + TX, Fluhexafon + TX, Flumethrin + TX, Fluopyram + TX, Fluvalinate + TX, Flupyradifurone + TX,Flupyrimin + TX, Flupyroxystrobin + TX, Fluralaner + TX, Fluvalinate + TX, Fluxametamide + TX, Formaldehyde + TX, fosthiazate + TX, Fosthietan + TX, Frontalin + TX, Furfural + TX, lambda - cyhalothrin + TX, (1:1 mixture of (Z,E) and (Z,Z) isomers of hexadec-7,11-dien-1-yl acetate) + TX, cotton boll weevil sex pheromone (grandlure) + TX, cotton boll weevil sex pheromone I + TX, cotton boll weevil sex pheromone II + TX, cotton boll weevil sex pheromone III + TX, cotton boll weevil sex pheromone IV + TX, Granulovirus + TX, guadipyr + TX, GY-81 + TX, halfenprox + TX, halofenozide + TX, Harpin + TX, Helicoverpa armigera Nucleopolyhedrovirus + TX, Helicoverpa zea NPV + TX, Helicoverpa zea Nucleopolyhedrovirus + TX, Helicoverpa punctigera Nucleopolyhedrovirus + TX, Helicoverpa virescens Nucleopolyhedrovirus + TX, hemel + TX, hempa + TX, heptafluthrin + TX, heterophos + TX, Heterorhabditis bacteriophora and Heterorhabditis megidis + TX, hexalure + TX, hexamide + TX, hexythiazox + TX, Hippodamia convergens + TX, hydramethylnon + TX, hydrargaphen + TX, slaked lime + TX, imicyafos + TX, imidacloprid + TX, imiprothrin + TX, Indazapyroxamet + TX, indoxacarb + TX, methyl iodide + TX, iprodione + TX, ipsdienol + TX, ipsenol + TX, isamidofos + TX, isazofos + TX, isocycloseram + TX, Isoflualanam (CAS No.: 2892524-05-7) + TX, isothioate + TX, ivermectin + TX, japonilure + TX, kappa-bifenthrin + TX,kappa-tefluthrin + TX, kasugamycin + TX, kasugamycin hydrochloride hydrate + TX, kinetin + TX, lambda-cyhalothrin + TX, ledprona, lepimectin, Leptomastix dactylopii, lineatin, litlure, looplure, lotilaner, lufenuron, Macrolophus caliginosus, Mamestra brassicae NPV, mecarphon, medlure, (3E,5Z)-tetradeca-3,5-dienoic acid, metaflumizone, metaldehyde, metam, metam potassium salt, metam sodium salt, Metaphycus helvolus, Metarhizium anisopliae var. acridum, Metarhizium anisopliae var. anisopliae, Metarhizium spp., metepa, methiocarb, methiotepa, methomyl, methoquin-butyl, methoxyfenozide, methylapholate, methyl bromide, methyl eugenol, methyl isothiocyanate, methyl neo-decanamide, metofluthrin, metolcarb, mexacarbate, milbemectin, milbemycin oxime, momfluorothrin, morzidMoxidectin + TX, Muscalure + TX, Muscodor albus 620 (NRRL accession number 30547) + TX, Muscodor roseus A3 - 5 (NRRL accession number 30548) + TX, Myrothecium verrucaria composition + TX, Nabam + TX, NC - 184 + TX, Neem - based product + TX, Neodiprion sertifer NPV and Neodiprion lecontei NPV + TX, Nickel bis(dimethyldithiocarbamate) + TX, Niclosamide + TX, Niclosamide - olamine + TX, Nicofluprole + TX, Nitenpyram + TX, Nithiazine + TX, Nitrapyrin + TX, Octadeca - 2,13 - dien - 1 - yl acetate + TX, Octadeca - 3,13 - dien - 1 - yl acetate + TX, Octhilinone + TX, Omethoate + TX, cis - 8 - Dodecenyl acetate (orfralure) + TX, Orius spp. + TX, Ethyl 4 - methyloctanoate (oryctalure) + TX, Lepidopteran pheromone 141 (ostramone) + TX, Oxamate + TX, Oxamyl + TX, Oxazosulfyl + TX, Oxolinic acid + TX, Oxytetracycline + TX, Paecilomyces fumosoroseus + TX, Paecilomyces lilacinus + TX, Parathion - ethyl + TX, Pasteuria nishizawae + TX, Pasteuria penetrans + TX, Pasteuria ramosa + TX, Pasteuria thornei + TX, Pasteuria usgae (microbial insecticide) + TX, Thymol (P - cymene) + TX, Penfluron + TX, Pentachlorophenol + TX, Permethrin + TX,Phenothrin + TX, Phorate + TX, Phosphamidon + TX, Phosphocarb + TX, Phytoseiulus persimilis + TX, Picaridin + TX, Piperazine + TX, Piperonyl butoxide + TX, Pirimicarb + TX, Pirimiphos-ethyl + TX, Pirimiphos-methyl + TX, Plutella xylostella granulosis virus + TX, Plutella xylostella nuclear polyhedrosis virus + TX, Polyhedrosis virus + TX, Potassium, Molybdenum and Manganese chelated with EDTA + TX, Potassium ethyl xanthate + TX, Potassium hydroxyquinoline sulfate + TX, Prallethrin + TX, Probenazole + TX, Profenofos + TX, Profluthrin + TX, Propargite + TX, Propetamphos + TX, Propoxur + TX, Prothiophos + TX, Protrifenbute + TX, Pyflubumide + TX, Pymetrozine + TX, Pyraclofos + TX, Pyrafluprole + TX, Pyrethrum + TX, Pyridaben + TX, Pyridalyl + TX, Pyridin-4-amine + TX, Pyrifluquinazon + TX, Pyrimidifen + TX, Pyriminostrobin + TX, Pyriprole + TX, Pyriprole [394730-71-3] + TX, Pyriproxyfen + TX, QRD 420 (Terpenoid blend) + TX, QRD 452 (Terpenoid blend) + TX, QRD 460 (Terpenoid blend) + TX, Quillaja saponaria + TX, Quinoclamine + TX, Quinonamid + TX, Resmethrin + TX, Rhodococcus globerulus AQ719 (NRRL accession number B-21663) + TX,Sarolaner + TX, S - bioallethrin + TX, Sebufos + TX, Selamectin + TX, Siglure + TX, Silafluofen + TX, Simazine + TX, Sodium pentachlorophenate + TX, Sordidin + TX, Spidoxamat + TX, Spinetoram + TX, Spinosad + TX, Spirobudifen + TX, Spirodiclofen + TX, Spiromesifen + TX, Spiropidion + TX, Spirotetramat + TX, Spodoptera exigua multicapsid nuclear polyhedrosis virus + TX, Spodoptera frugiperda nuclear polyhedrosis virus + TX, Steinernema bibionis + TX, Steinernema carpocapsae + TX, Steinernema feltiae + TX, Steinernema glaseri + TX, Steinernema riobrave + TX, Steinernema riobravis + TX, Steinernema scapterisci + TX, Steinernema spp. + TX, Streptomyces galbus (NRRL accession number 30232) + TX, Streptomyces spp. (NRRL accession number B - 30145) + TX, Streptomycin + TX, Streptomycin sulfate + TX, Strychnine + TX, Sulcatol + TX, Sulfoxaflor + TX, Tazimcarb + TX, Tebufenozide + TX, Tebufenpyrad + TX, Tebupirimiphos + TX, Tecloftalam + TX, Tefluthrin + TX, Temephos + TX, Tepa + TX,terbam + TX, terbufos + TX, terpene blend + TX, tetrachlorantraniliprole + TX, tetrachlorothiophene + TX, tetradec - 11 - en - 1 - yl acetate + TX, tetradiphon + TX, tetramethrin + TX, tetramethylfluthrin + TX, tetranactin + TX, tetraniliprole + TX, theta - cypermethrin + TX, thiacloprid + TX, thiafenox + TX, thiamethoxam + TX, thiocyclam + TX, thiodicarb + TX, thiofanox + TX, thiohempa + TX, thiomersal + TX, thiometon + TX, thionazin + TX, thiophanate + TX, thiosultap + TX, thiotepa + TX, tigolaner + TX, tiorantraniliprole + TX, tioxazafen + TX, tolfenpyrad + TX, toxaphene + TX, tralomethrin + TX, transfluthrin + TX, tritramectin + TX, triazamate + TX, triazophos + TX, triazuron + TX, tributyltin oxide + TX, trichlorfon + TX, trichloronate + TX, trichlorphon + TX, Trichogramma spp. + TX, trifenmorph + TX, trifluenfuronate + TX, triflumezopyrim + TX, trimedlure + TX, trimedlure A + TX, trimedlure B1 + TX, trimedlure B2 + TX, trimedlure C + TX, trimethacarb + TX, triphenyltin acetate + TX, triphenyltin hydroxide + TX,trunc-call+TX, tylopyrazoflor+TX, Typhlodromus occidentalis+TX, uredepa+TX, Verticillium lecanii+TX, Verticillium species+TX, xylenols+TX, YI-5302+TX, zeatin+TX, zeta-Cypermethrin+TX;;

[0312] N-[(1R)-1-Benzyl-3-chloro-1-methyl-but-3-enyl]-8-fluoro-quinoline-3-carboxamide + TX, N-[(1S)-1-benzyl-3-chloro-1-methyl-but-3-enyl]-8-fluoro-quinoline-3-carboxamide + TX, N-ethyl-N'-[5-methoxy-2-methyl-4-[(2-trifluoromethyl)tetrahydrofuran-2-yl]phenyl]-N-methyl-formamidine (these compounds can be prepared by the methods described in WO2019 / 110427) + TX, (3',4',5'-trifluoro-biphenyl-2-yl)-amide + TX, (3-methylisoxazol-5-yl)-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methanone (these compounds can be prepared by the methods described in WO 2017 / 220485) + TX, 2-amino-6-methyl-pyridine-3-carboxylic acid (4-phenoxyphenyl)methyl ester (this compound can be prepared by the methods described in WO 2014 / 006945) + TX, (5-methyl-2-pyridyl)-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methanone + TX, (7E,9Z)-dodeca-7,9-dien-1-yl acetate + TX, (9Z,11E)-tetradeca-9,11-dien-1-yl acetate + TX, (9Z,12E)-tetradeca-9,12-dien-1-yl acetate + TX, (E)-6-methylhept-2-en-4-ol + TX, (E)-dec-5-en-1-yl acetate and (E)-dec-5-en-1-ol + TX, (E)-tridec-4-en-1-yl acetate + TX, (E,Z)-tetradeca-4,10-dien-1-yl acetate + TX, + TX, (R)-3-(difluoromethyl)-1-methyl-N-[1,1,3-trimethylinden-4-yl]pyrazole-4-carboxamide + TX, (Z)-dodec-7-en-1-yl acetate + TX, (Z)-hexadec-11-en-1-yl acetate + TX, (Z)-hexadec-11-enal + TX, (Z)-hexadec-13-en-11-yn-1-yl acetate + TX, (Z)-heneicos-13-en-10-one + TX, (Z)-tetradec-7-en-1-al + TX, (Z)-tetradec-9-en-1-ol + TX, (Z)-tetradec-9-en-1-yl acetate + TX, (Z,2E)-5-[1-(2,4-dichlorophenyl)pyrazol-3-yl]oxy-2-methoxyimino-N,3-dimethyl-pent-3-enamine (this compound can be prepared by the methods described in WO 2018 / 153707) + TX, (Z,2E)-5-[1-(4-chlorophenyl)pyrazol-3-yl]oxy-2-methoxyimino-N,3-dimethyl-pent-3-enamine + TX, + TX,[2-[3-[2-[1-[2-[3,5-bis(difluoromethyl)pyrazol-1-yl]acetyl]-4-piperidinyl]thiazol-4-yl]-4,5-dihydroisoxazol-5-yl]-3-chloro-phenyl]methanesulfonate + TX, 1-(4,5-dimethylbenzimidazol-1-yl)-4,4,5-trifluoro-3,3-dimethyl-isoquinoline + TX, 1-(4,5-dimethylbenzimidazol-1-yl)-4,4-difluoro-3,3-dimethyl-isoquinoline + TX, 1-(6,7-dimethylpyrazolo[1,5-a]pyridin-3-yl)-4,4,5-trifluoro-3,3-dimethyl-isoquinoline + TX, 1-(6,7-dimethylpyrazolo[1,5-a]pyridin-3-yl)-4,4,6-trifluoro-3,3-dimethyl-isoquinoline + TX, 1-(6-chloro-7-methyl-pyrazolo[1,5-a]pyridin-3-yl)-4,4-difluoro-3,3-dimethyl-isoquinoline (these compounds can be prepared by the methods described in WO2017 / 025510) + TX, 1,1-bis(4-chlorophenyl)-2-ethoxyethanol + TX, 1,1-dichloro-2,2-bis(4-ethylphenyl)ethane + TX, 1,2-dibromo-3-chloropropane + TX, 1,2-dichloropropane and 1,3-dichloropropene + TX, 1,3-dichloropropene + TX, 1,3-dimethoxy-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]urea + TX, 1-[2-[[1-(4-chlorophenyl)pyrazol-3-yl]oxymethyl]-3-methyl-phenyl]-4-methyl-tetrazol-5-one + TX, 10-dien-1-yl acetate + TX, 14-methyloctadec-1-ene + TX, 1-bromo-2-chloroethane + TX, 1-dichloro-1-nitroethane + TX, 1-hydroxy-1H-pyridine-2-thione + TX, 1-methoxy-3-methyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]urea + TX, 1-methyl-4-[3-methyl-2-[[2-methyl-4-(3,4,5-trimethylpyrazol-1-yl)phenoxy]methyl]phenyl]tetrazol-5-one + TX, 2-(difluoromethyl)-N-((3R)-1,1,3-trimethylinden-4-yl)pyridine-3-carboxamide + TX, 2-(difluoromethyl)-N-((3R)-1,1,3-trimethylinden-4-yl)pyridine-3-carboxamide + TX, 2-(1,3-dithiolan-2-yl)phenyl dimethylcarbamate + TX, 2-(2-butoxyethoxy)ethyl piperate + TX, 2-(2-butoxyethoxy)ethyl thiocyanate + TX, 2-(4,5-dimethyl-1,3-dioxolan-2-yl)phenyl methylcarbamate + TX, 2-(4-chloro-3,5-dimethylphenoxy)ethanol + TX,2-(Difluoromethyl)-N-(3-ethyl-1,1-dimethyl-indan-4-yl)pyridine-3-carboxamide + TX, 2-(Difluoromethyl)-N-[(3R)-3-ethyl-1,1-dimethyl-indan-4-yl]pyridine-3-carboxamide + TX, 2-(Difluoromethyl)-N-[(3S)-3-ethyl-1,1-dimethyl-indan-4-yl]pyridine-3-carboxamide (This compound can be prepared by the method described in WO 2014 / 095675) + TX, 2-(Difluoromethyl)-N-[3-ethyl-1,1-dimethyl-indan-4-yl]pyridine-3-carboxamide + TX, 2-(Octylthio)ethanol + TX, 2,2,2-Trichloro-1-(3,4-dichlorophenyl)ethyl acetate + TX, 2,2-Dichlorovinyl 2-ethylsulfinylethyl methyl phosphate + TX, 2,2-Difluoro-N-methyl-2-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]acetamide + TX, 2,4-Dichlorophenyl benzenesulfonate + TX, 2,6-Dimethyl-1H,5H-[1,4]dithieno[2,3-c:5,6-c']dipyrrole-1,3,5,7(2H,6H)-tetraone (This compound can be prepared by the method described in WO 2011 / 138281) + TX, 2-[2-Fluoro-6-[(8-fluoro-2-methyl-3-quinolyl)oxy]phenyl]propan-2-ol + TX, 2-[6-(4-Bromophenoxy)-2-(trifluoromethyl)-3-pyridyl]-1-(1,2,4-triazol-1-yl)propan-2-ol (This compound can be prepared by the method described in WO 2017 / 029179) + TX, 2-[6-(4-Chlorophenoxy)-2-(trifluoromethyl)-3-pyridyl]-1-(1,2,4-triazol-1-yl)propan-2-ol (This compound can be prepared by the method described in WO 2017 / 029179) + TX, 2-Chlorovinyl diethyl phosphate + TX, 2-Fluoro-N-methyl-N-1-naphthylacetamide + TX, 2-Imidazolidinone + TX, 2-Isovalerylindane-1,3-dione + TX, 2-Methyl(prop-2-ynyl)aminophenyl methylcarbamate + TX, 2-Oxo-N-propyl-2-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]acetamide (This compound can be prepared by the method described in WO 2018 / 065414) + TX, 2-Cyanothioethyl laurate + TX, 3-(4,4-Difluoro-3,3-dimethyl-1-isoquinolinyl)-7,8-dihydro-6H-cyclopenta[e]benzimidazole (These compounds can be prepared by the method described in WO2016 / 156085) + TX, 3-(4,4-Difluoro-3,4-dihydro-3,3-dimethylisoquinolin-1-yl)quinolone + TX, 3-(4-Chlorophenyl)-5-methylrhodanine + TX,3-(Difluoromethyl)-1-methyl-N-[1,1,3-trimethylinden-4-yl]pyrazole-4-carboxamide + TX, 3,4-dichlorotetrahydrothiophene 1,1-dioxide + TX, 3-[2-(1-chlorocyclopropyl)-3-(2-fluorophenyl)-2-hydroxy-propyl]imidazole-4-carbonitrile (this compound can be prepared by the method described in WO 2016 / 156290) + TX, 3-[2-(1-chlorocyclopropyl)-3-(3-chloro-2-fluorophenyl)-2-hydroxy-propyl]imidazole-4-carbonitrile (this compound can be prepared by the method described in WO2016 / 156290) + TX, 3-bromo-1-chloroprop-1-ene + TX, 3-chloro-6-methyl-5-phenyl-4-(2,4,6-trifluorophenyl)pyridazine + TX, 3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid + TX, 3-ethyl-1-methoxy-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]urea + TX, 3-methyl-1-phenylpyrazol-5-yl dimethylcarbamate + TX, 4-(2-bromo-4-fluorophenyl)-N-(2-chloro-6-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine + TX, 4-(2,6-difluorophenyl)-6-methyl-5-phenyl-pyridazine-3-carbonitrile + TX, 4-(2-bromo-4-fluoro-phenyl)-N-(2-chloro-6-fluoro-phenyl)-2,5-dimethyl-pyrazol-3-amine + TX, 4-(quinoxalin-2-ylamino)benzenesulfonamide + TX, 4,4-difluoro-1-(5-fluoro-4-methyl-benzoimidazol-1-yl)-3,3-dimethyl-isoquinoline + TX, 4,4-difluoro-3,3-dimethyl-1-(6-methylpyrazolo[1,5-a]pyridin-3-yl)isoquinoline + TX, 4,4-difluoro-3,3-dimethyl-1-(7-methylpyrazolo[1,5-a]pyridin-3-yl)isoquinoline + TX, 4,4-dimethyl-2-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]isoxazolidin-3-one + TX, 4-[[6-[2-(2,4-difluorophenyl)-1,1-difluoro-2-hydroxy-3-(1,2,4-triazol-1-yl)propyl]-3-pyridyl]oxy]benzonitrile + TX, 4-[[6-[2-(2,4-difluorophenyl)-1,1-difluoro-2-hydroxy-3-(5-thioalkyl-1,2,4-triazol-1-yl)propyl]-3-pyridyl]oxy]benzonitrile + TX, 4-[[6-[2-(2,4-difluorophenyl)-1,1-difluoro-2-hydroxy-3-(5-thioxo-4H-1,2,4-triazol-1-yl)propyl]-3-pyridyl]oxy]benzonitrile + TX, 4-chloro-2-(2-chloro-2-methyl-propyl)-5-[(6-iodo-3-pyridyl)methoxy]pyridazin-3-one + TX, 4-chlorophenyl phenyl sulfone + TX,4-Methyl(prop-2-ynyl)amino-3,5-dimethylbenzyl methylcarbamate + TX, 4-Methylnon-5-ol and 4-Methylnon-5-one + TX, 5-(1,3-Benzodioxol-5-yl)-3-hexylcyclohex-2-enone + TX, 5,5-Dimethyl-2-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]isoxazolidin-3-one + TX, 5,5-Dimethyl-3-oxocyclohex-1-enyl dimethylcarbamate + TX, 5-Amino-1,3,4-thiadiazole-2-thiol zinc salt (2:1) + TX, 5-Methyl-6-thioxo-1,3,5-thiadiazin-3-ylacetic acid + TX, 6-Chloro-3-(3-cyclopropyl-2-fluorophenoxy)-N-[2-(2,4-dimethylphenyl)-2,2-difluoroethyl]-5-methylpyridazine-4-carboxamide (which can be prepared by the method described in WO 2020 / 109391) + TX, 6-Chloro-3-(3-cyclopropyl-2-fluorophenoxy)-N-[2-(3,4-dimethylphenyl)-2,2-difluoroethyl]-5-methylpyridazine-4-carboxamide (which can be prepared by the method described in WO 2020 / 109391) + TX, 6-Chloro-4,4-difluoro-3,3-dimethyl-1-(4-methylbenzimidazol-1-yl)isoquinoline + TX, 6-Chloro-N-[2-(2-chloro-4-methylphenyl)-2,2-difluoroethyl]-3-(3-cyclopropyl-2-fluorophenoxy)-5-methylpyridazine-4-carboxamide (which can be prepared by the method described in WO 2020 / 109391) + TX, 6-Ethyl-5,7-dioxopyrrolo[4,5][1,4]dithieno[1,2-c]isothiazole-3-carbonitrile + TX, 6-Isopentenylaminopurine + TX, 8-Fluoro-N-[(1R)-1-[(3-fluorophenyl)methyl]-1,3-dimethylbutyl]quinoline-3-carboxamide + TX, 8-Fluoro-N-[(1S)-1-[(3-fluorophenyl)methyl]-1,3-dimethylbutyl]quinoline-3-carboxamide + TX, 8-Hydroxyquinoline sulfate + TX, Acephate + TX, Acetoprole + TX, Alanap + TX, Alanap-S-methyl + TX, Acrylonitrile + TX, Adoxophyes orana GV + TX, Agrobacterium radiobacter + TX, Aldoxycarb + TX, Aldrin + TX, Aloealomycin + TX, Benethacarb + TX, α-Chloroalcohol + TX, α-Ecdysone + TX, α-Multigrin + TX, Aluminium phosphide + TX, Amblyseius species + TX, Apectotractin + TX, Amisulbrom + TX, Ascorbic acid + TX, Carbophenothion + TX, Carbaryl + TX, Amisulpride + TX, Indoxacarb + TX, Amisulpride + TX, Oxalic acid hydrogen amiton + TX, Amitraz + TX, Neonicotinoid + TX, Autographa celerio NPV + TX, Anastatus principii + TX,Ancymidol + TX, Anilazine + TX, Flubendiamide + TX, Anthraquinone + TX, Antu + TX, Aphytis melinus + TX, Aphelinus gossypii + TX, Aphidoletes aphidimyza + TX, Azamethiphos + TX, Aramite + TX, Arsenic trioxide + TX, Ethion + TX, Autographa californica multiple nucleopolyhedrovirus + TX, Azaconazole + TX, Pirimiphos-methyl + TX, Azobenzene + TX, Azinphos + TX, Azoxystrobin + TX, Bacillus sphaericus + TX, Bacillus thuringiensis δ-endotoxin + TX, Barium carbonate + TX, Barium hexafluorosilicate + TX, Barium polysulfide + TX, Bioallethrin + TX, Bayer 22 / 190 + TX, Bayer 22408 + TX, Beauveria brongniartii + TX, Benalaxyl + TX, Benzyl chloride + TX, Benomyl + TX, Benoxacor + TX, Benthiavalicarb + TX, Benthiavalicarb-isopropyl + TX, Benzovindiflupyr + TX, Benzyl benzoate + TX, β-Cyfluthrin + TX, β-Cypermethrin + TX, Bassa + TX, Bioethanomethrin + TX, Bioresmethrin + TX, Bis(2-chloroethyl) ether + TX, Bis(tributyltin) oxide + TX, Bisazir + TX, Biminthiazole + TX, Bitertanol + TX, Bixafen + TX, Blasticidin-S + TX, Borax + TX, Bordeaux mixture + TX, Boscalid + TX, Dendroctonus brevicomis aggregation pheromone + TX, Bromadiolone + TX, Bromfenvinfos + TX, Bromethalin + TX, Bromethanil + TX, Bromfenvinfos + TX, Bromoacetamide + TX, Bromocylen + TX, Bromo-DDT + TX, Bromophos + TX, Bromopropylate + TX, Furconazole + TX, Bronopol + TX, Bufencarb + TX, Bupirimate + TX, Buprofezin + TX, Busulfan + TX, Butoate + TX, Butocarboxim + TX, Butonate + TX, Butyl carbitol + TX, Butoxycarboxim + TX, Butylpyridaben + TX, Calcium arsenate + TX, Calcium cyanide + TX, Calcium polysulfide + TX, Camphechlor + TX, Captafol + TX, Captan + TX, Carbaryl + TX, Carbendazim + TX, Carbon disulfide + TX, Carbon tetrachloride + TX, Carbophenothion + TX, Carboxin + TX, Cartap hydrochloride + TX, Veratrine + TX, Chinomethionat + TX, Chloralose + TX, Chlorbenside + TX, Chlorfenson + TX, Chlordane + TX, Chlordecone + TX, Chlordimeform + TX, Chlordimeform hydrochloride + TX, Chlorobenzilate + TX, Chlorfenson + TX, Chlorfensulphide + TX, Chlorobenzilate + TX, Chlorobenzilate + TX, Chlorothalonil + TX, Chloroxon + TX, Chlorpyrazophos + TX, Chlorpyrifos + TX,Chlozolinate + TX, Cholecalciferol + TX, Chrysoperla carnea + TX, Pyrethrins I + TX, Pyrethrins II + TX, Pyrethrins + TX, Cis-methrin + TX, Cis-resmethrin + TX, Cypermethrin + TX, Cloethocarb + TX, Dodecadienol + TX, Codlemone + TX, Cupric acetoarsenite + TX, Cupric arsenate + TX, Cupric caprylate + TX, Cupric hydroxide + TX, Cupric naphthenate + TX, Cupric oleate + TX, Cupric oxide + TX, Copper oxychloride + TX, Copper sulfate + TX, Warfarin + TX, Coumatetralyl + TX, Coumaphos + TX, Menadione + TX, Jiaxiangjunzhi + TX, Chlorfenvinphos + TX, Cicloprothrin + TX, Cresol + TX, Primidone + TX, Amiton + TX, Cacodyl phosphate + TX, Crufomate + TX, Cryolite + TX, Cryptolaemus montrouzieri + TX, CS 708 + TX, Cuelure + TX, Thiofanox + TX, Cyanofenphos + TX, Cyanophos + TX, Carbophenothion + TX, Cythioate + TX, Cipconazole + TX, Cyprodinil + TX, Cythioate + TX, Cytokinin + TX, Microplitis sibiricus + TX, DAEP + TX, Dazomet + TX, DCIP + TX, DCPM + TX, DDT + TX, Imazalil + TX, Desmethyl carbofuran + TX, Demeton-S-methyl + TX, Demeton-O + TX, Demeton-O-methyl + TX, Demeton-S + TX, Demeton-S-methyl + TX, Demeton-S-methylsulfon + TX, Dioxathion + TX, Dibutyl adipate + TX, Dibutyl phthalate + TX, Dibutyl succinate + TX, Isochlorphos + TX, Dichlofluanid + TX, Dioxathion + TX, Tolylfluanid + TX, Dichlone + TX, Dichlorophen + TX, Dichlorvos + TX, Dichlozolin + TX, Dicapthon + TX, Diclocymet + TX, Diclomezine + TX, Dichloran + TX, Dicresyl + TX, Cyhalothrin + TX, Dicyclopentadiene + TX, Dieldrin + TX, Dicofol + TX, Diethofencarb + TX, Diethyl 5-methylpyrazol-3-yl phosphate + TX, DEET + TX, Flocoumafen + TX, Difenoconazole + TX, Bromadiolone + TX, Fipronil + TX, Diglyphus isaea + TX, Aminophylline + TX, Dimethomorph + TX, Dimefluthrin + TX, Methamidophos + TX, Carbaryl + TX, Iprodione + TX, Dimethoxy + TX, Methacrifos + TX, Dimetilan + TX, Trifloxystrobin + TX, Dinocap + TX,Dinocap (dinex-diclexine) + TX, Diniconazole + TX, Nitrothal-isopropyl - 4 + TX, Nitrothal-isopropyl - 6 + TX, Binapacryl + TX, Nitropentyl + TX, Nitrophenol + TX, Nitrophenol + TX, DNOC + TX, Nitrooctyl Acaricide + TX, Nitrobutyl + TX, Ethiprole + TX, Sulprofos + TX, Dichlorvos + TX, Warfarin + TX, Sulfodiphenyl + TX, Tricyclazole + TX, Pyrithione + TX, 1,2-Epoxynonadecane + TX, Sulfuron + TX, Endothall + TX, Thionazin + TX, 1-[[4-[(Z)-2-Ethoxy-3,3,3-trifluoro-prop-1-enyloxy]phenyl]methyl]pyrazole-3-carboxylic acid ethyl ester (which can be prepared by the method described in WO 2020 / 056090), 1-[[4-[[2-(Trifluoromethyl)-1,3-dioxolan-2-yl]methoxy]phenyl]methyl]pyrazole-3-carboxylic acid ethyl ester (which can be prepared by the method described in WO 2020 / 056090), 1-[[4-[5-(Trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]pyrazole-4-carboxylic acid ethyl ester, 1-[[5-[5-(Trifluoromethyl)-1,2,4-oxadiazol-3-yl]-2-thienyl]methyl]pyrazole-4-carboxylic acid ethyl ester (this compound can be prepared by the method described in WO 2018 / 158365), Ethyl 4-methylcaprylate, Ethyl formate, 2-Ethylhexylene glycol, Ethylene dibromide, Ethylene dichloride, Ethylene oxide, Edifenphos, Etrimfos, Eugenol, EXD, Oxfendazole, Farnesol, Farnesol with Nerolidol, Fenamidone, Sodium thiram, Enami fungin, Fenarimol, Fenazaquin, Myclobutanil, Fenbutatin oxide, Fenchlorphos, Ethiofencarb, Methfuroxam, Fenhexamid, Fenitrothion, Benothiocarb, Famoxadone, Pyrazophos, Benzoximate,Cypermethrin + TX, Fenpropidin + TX, Fenpropimorph + TX, Tebufenpyrad + TX, Ametoctradin + TX, Fenpyroximate + TX, Chlorfenson + TX, Fensulfothion + TX, Fenthion + TX, Ethion + TX, Triphenyltin + TX, Dinitrofluorobenzene + TX, Ferric dimethyldithiocarbamate + TX, Ferimzone + TX, Ferric phosphate + TX, Flocoumafen + TX, Fluopyram + TX, Fluazinam + TX, Flufenacet + TX, Flufenerim + TX, Flufenoxuron + TX, Fludioxonil + TX, Fluacrypyrim + TX, Fluoxastrobin + TX, Fluopyram + TX, Fluopyram + TX, Fluvalinate + TX, Fluoroacetamide + TX, Flupoxam + TX, Fluoxastrobin + TX, Fluoxastrobin + TX, Fluopyram + TX, Flupropacil + TX, Flupropacil hydrochloride + TX, Flusilazole + TX, Flusilazole + TX, Sulfametamide + TX, Fluoxastrobin + TX, Flutolanil + TX, Fluxapyroxad + TX, FMC 1137 + TX, Folpet + TX, Formaldehyde + TX, Formetanate + TX, Formetanate hydrochloride + TX, Carbaryl + TX, Aluminum tris(ethyl phosphite) + TX, Butathiofos + TX, Phosphamidon + TX, Butocarboxim + TX, Southern pine beetle aggregation pheromone + TX, Fuberidazole + TX, Furalaxyl + TX, Furametpyr + TX, Furathiocarb + TX, Pyrethrum + TX, Furfural + TX, γ-HCH + TX, Guazatine + TX, Lurem-TR + TX, Lurem-TR I + TX, Lurem-TR II + TX, Lurem-TR III + TX, Lurem-TR IV + TX, Guazatine acetate + TX, Guazatine octanoate + TX, Bifenazate + TX, HCH + TX, Altretamine + TX, Hexamethylphosphoramide + TX, HEOD + TX, Heptachlor + TX, Phosalone + TX, Heterorhabditis bacteriophora and Heterorhabditis megidis + TX, Hexaconazole + TX, Hexadecyl cyclopropanecarboxylate + TX, Hexalure + TX, Hexuron + TX, HHDN + TX, Chilocorus stigma + TX, Merthiolate + TX, Slaked lime + TX, Hydrogen cyanide + TX, Hymexazol + TX, Quinocarb + TX, Imazalil + TX, Imibenconazole + TX, Guazatine + TX, Indoxacarb + TX, Tebuconazole + TX, Isotriazolone + TX, Isopropylquinalphos + TX, Iprobenfos + TX, Iprodione + TX, Propineb + TX, Ipsdienol + TX, Ipsenol + TX, IPSP + TX, Isocarbophos + TX, Chlorpyrifos-methyl + TX, Carbophenothion + TX, Isocarbophos + TX, Isodrin + TX, Isofenphos + TX, Isotianil + TX, Isopyrazam + TX, Isothiazolinone + TX, Oxydemeton-methyl + TX, Isoprothiolane + TX, Pyraclostrobin + TX, Isotianil + TX, Oxydemeton-methyl + TX,Scarab sex pheromone + TX, pyrethrins I + TX, pyrethrins II + TX, iodofenphos + TX, juvenile hormone I + TX, juvenile hormone II + TX, juvenile hormone III + TX, thienylpyrethrin + TX, kasugamycin + TX, kasugamycin hydrochloride hydrate + TX, chloropentalene + TX, kinetin + TX, kinoprene + TX, kresoxim-methyl + TX, lead arsenate + TX, Encarsia citrina + TX, bromfenvinfos + TX, lindane + TX, trimethyl dioxatricyclononane + TX, acetamiprid + TX, Noctuidae sex pheromone + TX, Trichoplusia ni sex pheromone + TX, lvbenmixianan, fosthiazate + TX, Miridae + TX, magnesium phosphide + TX, propargite + TX, Mamestra brassicae NPV + TX, mancozeb + TX, mancopper + TX, mandestrobin + TX, mandipropamid + TX, maneb + TX, azinphos + TX, isopropylphenyl methylcarbamate + TX, mecarbam + TX, methyl mecarbam + TX, sex pheromone lure + TX, fluopyram + TX, megatomoic acid + TX, methidathion + TX, cymoxanil + TX, empenthrin + TX, dioxathion + TX, fenfuram + TX, mercury oxide + TX, mercurous chloride + TX, thiofanox + TX, methiasulfoxon + TX, metalaxyl + TX, metam-sodium + TX, metam-potassium + TX, metam-sodium salt + TX, Metaphycus flavus + TX, Metarhizium anisopliae var. acridum + TX, Metarhizium anisopliae var. anisopliae + TX, picolinafen + TX, metconazole + TX, methyl thiofanox + TX, crotoxyphos + TX, methylsulfonyl fluoride + TX, sulfallate + TX, methiocarb + TX, butenamiphos + TX, methoprene + TX, mequinol + TX, tetramethrin + TX, methoxychlor + TX, methyl (Z)-2-(5-cyclohexyl-2-methylphenoxy)-3-methoxyprop-2-enoate + TX, methyl (Z)-2-(5-cyclopentyl-2-methylphenoxy)-3-methoxyprop-2-enoate (These compounds can be prepared by the methods described in WO2020 / 193387) + TX, methyl (Z)-2-[5-(3-isopropylpyrazol-1-yl)-2-methylphenoxy]-3-methoxyprop-2-enoate + TX, methyl (Z)-3-methoxy-2-[2-methyl-5-(3-propylpyrazol-1-yl)phenoxy]prop-2-enoate + TX, methyl (Z)-3-methoxy-2-[2-methyl-5-(4-propyl-1,2,3-triazol-2-yl)phenoxy]prop-2-enoate + TX, methyl (Z)-3-methoxy-2-[2-methyl-5-[3-(trifluoromethyl)pyrazol-1-yl]phenoxy]prop-2-enoate (These compounds can be prepared by the methods described in WO2020 / 079111) + TX, methyl (Z)-3-methoxy-2-[2-methyl-5-[4-(trifluoromethyl)-1,2,3-triazol-2-yl]phenoxy]prop-2-enoate + TX,Azamethiphos + TX, Methyl bromide + TX, Ethyl 4,6-dinitro-2-(trifluoromethyl)phenylcarbamate + TX, Methyl isothiocyanate + TX, Methyl N-[[4-[1-(2,6-difluoro-4-isopropylphenyl)pyrazol-4-yl]-2-methylphenyl]methyl]carbamate (which can be prepared by the method described in WO 2020 / 097012) + TX, Methyl N-[[4-[1-(4-cyclopropyl-2,6-difluorophenyl)pyrazol-4-yl]-2-methylphenyl]methyl]carbamate (which can be prepared by the method described in WO 2020 / 097012) + TX, Methyl N-[[5-[4-(2,4-dimethylphenyl)-1,2,4-triazol-2-yl]-2-methylphenyl]methyl]carbamate + TX, 1,1,1-Trichloroethane + TX, Dichloromethane + TX, Methyl neodecanoamide + TX, Metiram + TX, MTMC + TX, Metominsstrobin + TX, Metaflumizone + TX, Benzovindiflupyr + TX, Tetraconazole + TX, MGK 264 + TX, Milbemycin + TX, Proafiphen + TX, Mirex + TX, Monocrotophos + TX, Acephate + TX, Chlorflurenol + TX, Moxidectin + TX, Methyl eugenol + TX, Myclobutanil + TX, Methfuroxam + TX, Myrothecium verrucaria composition + TX, N-((1R)-1-benzyl-3-chloro-1-methylbut-3-enyl)-8-fluoroquinoline-3-carboxamide (These compounds can be prepared by the method described in WO2017 / 153380) + TX, N-((1S)-1-benzyl-3-chloro-1-methylbut-3-enyl)-8-fluoroquinoline-3-carboxamide (These compounds can be prepared by the method described in WO2017 / 153380) + TX, N'-(2,5-dimethyl-4-phenoxyphenyl)-N-ethyl-N-methylformamidine + TX, N'-(2-chloro-5-methyl-4-phenoxyphenyl)-N-ethyl-N-methylformamidine + TX, N,2-dimethoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]propanamide + TX, N,N-dimethyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]-1,2,4-triazol-3-amine (These compounds can be prepared by the method described in WO2017 / 055473 + TX, WO 2017 / 055469 + TX, WO 2017 / 093348 and WO 2017 / 118689) + TX, N-[(1R)-1-benzyl-1,3-dimethylbutyl]-7,8-difluoroquinoline-3-carboxamide + TX, N-[(1R)-1-benzyl-1,3-dimethylbutyl]-8-fluoroquinoline-3-carboxamide + TX, N-[(1R)-1-benzyl-3,3,3-trifluoro-1-methylpropyl]-8-fluoroquinoline-3-carboxamide + TX,N-[(1S)-1-Benzyl-1,3-dimethyl-butyl]-7,8-difluoro-quinoline-3-carboxamide + TX, N-[(1S)-1-benzyl-1,3-dimethyl-butyl]-8-fluoro-quinoline-3-carboxamide + TX, N-[(1S)-1-benzyl-3,3,3-trifluoro-1-methyl-propyl]-8-fluoro-quinoline-3-carboxamide + TX, N-[(E)-methoxyiminomethyl]-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide + TX, N-[(Z)-methoxyiminomethyl]-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide + TX, N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]propanamide + TX, N-[2-[2,4-dichlorophenoxy]phenyl]-3-(difluoromethyl)-1-methyl-pyrazole-4-carboxamide + TX, N-[2-[2-chloro-4-(trifluoromethyl)phenoxy]phenyl]-3-(difluoromethyl)-1-methyl-pyrazole-4-carboxamide + TX, N'-[2-chloro-4-(2-fluorophenoxy)-5-methyl-phenyl]-N-ethyl-N-methyl-formamidine (this compound can be prepared by the method described in WO2016 / 202742) + TX, N'-[4-(4,5-dichlorothiazol-2-yl)oxy-2,5-dimethyl-phenyl]-N-ethyl-N-methyl-formamidine + TX, N'-[5-bromo-2-methyl-6-(1-methyl-2-propoxy-ethoxy)-3-pyridyl]-N-ethyl-N-methyl-formamidine + TX, N'-[5-bromo-2-methyl-6-(1-methyl-2-propoxy-ethoxy)-3-pyridyl]-N-isopropyl-N-methyl-formamidine (these compounds can be prepared by the method described in WO2015 / 155075) + TX, N'-[5-bromo-2-methyl-6-(2-propoxypropoxy)-3-pyridyl]-N-ethyl-N-methyl-formamidine (this compound can be prepared by the method described in IPCOM000249876D) + TX, N'-[5-bromo-2-methyl-6-[(1R)-1-methyl-2-propoxy-ethoxy]-3-pyridyl]-N-ethyl-N-methyl-formamidine + TX, N'-[5-bromo-2-methyl-6-[(1S)-1-methyl-2-propoxy-ethoxy]-3-pyridyl]-N-ethyl-N-methyl-formamidine + TX, N'-[5-chloro-2-methyl-6-(1-methyl-2-propoxy-ethoxy)-3-pyridyl]-N-ethyl-N-methyl-formamidine + TX, N-[N-methoxy-C-methyl-carbodiimide]-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide (these compounds can be prepared by the method described in WO 2018 / 202428) + TX,N’-[4-(1-cyclopropyl-2,2,2-trifluoro-1-hydroxy-ethyl)-5-methoxy-2-methyl-phenyl]-N-isopropyl-N-methyl-formamidine (These compounds can be prepared by the methods described in WO2018 / 228896) + TX, sodium thiram + TX, naphthalophos + TX, dichlorvos + TX, naphthalene + TX, NC-170 + TX, Neodiprion sertifer NPV and Neodiprion lecontei NPV + TX, nerolidol + TX, N-ethyl-2-methyl-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]propanamide + TX, N-ethyl-N’-[5-methoxy-2-methyl-4-[(2-trifluoromethyl)oxetan-2-yl]phenyl]-N-methyl-formamidine + TX, nickel bis(dimethyldithiocarbamate) + TX, niclosamide ethanolamine + TX, nicotine + TX, nicotine sulfate + TX, fluphenoxur + TX, nikkomycin + TX, N-isopropyl-N’-[5-methoxy-2-methyl-4-(2,2,2-trifluoro-1-hydroxy-1-phenyl-ethyl)phenyl]-N-methyl-formamidine + TX, nithiazine + TX, trichloromethylpyridine + TX, pentacyl + TX, pentacyl 1:1 zinc chloride complex + TX, phthalide + TX, N-methoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]cyclopropanecarboxamide + TX, N-methyl-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide + TX, N-methyl-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]thiobenzamide + TX, warfarin + TX, fluotrimazole + TX, O,O,O',O'-tetrapropyl dithiopyrophosphate + TX, (Z)-octadeca-2,13-dien-1-yl acetate + TX, (E)-octadeca-3,13-dien-1-yl acetate + TX, octhilinone + TX, furcarbanil + TX, oleic acid + TX, omethoate + TX, Helcon + TX, Orius species + TX, Oryctes rhinoceros aggregation pheromone + TX, triclopyricarb + TX, Ferochlor + TX, oxadixyl + TX, oxamate + TX, thiabendazole + TX, copper quinolate + TX, oxolinic acid + TX, oxycarboxin + TX, isoxathion + TX, sulfotep + TX, oxytetracycline + TX, paclobutrazol + TX, Paecilomyces fumosoroseus + TX, p-dichlorobenzene + TX, parathion + TX, methyl parathion + TX, blastricidin S + TX, penconazole + TX, tebuthiuron + TX, novaluron + TX, pentachlorophenol + TX, pentachlorophenyl laurate + TX, pythiobac + TX, permethrin + TX, PH 60-38 + TX, phenamacril + TX, fenthion + TX, phosdrin + TX, phosalone + TX, chlorpyrifos-methyl + TX, phosfolan + TX,Glyphosate + TX, parachlorothion + TX, phosphamidon + TX, phosphine + TX, phosphorus + TX, methyl phoxim + TX, phthalide + TX, Chilean phytoseiid mite + TX, piperazole + TX, picaridin + TX, picoxystrobin + TX, cypermethrin + TX, piperazine + TX, piperonyl butoxide + TX, synergistic aldehyde + TX, methamidophos + TX, polychlorinated dicyclopentadiene isomers + TX, chlorinated turpentine + TX, acaricide + TX, polyoxin + TX, potassium arsenite + TX, potassium ethyl xanthate + TX, potassium hydroxyquinoline sulfate + TX, potassium thiocyanate + TX, pp'-DDT + TX, precocious element I + TX, precocious element II + TX, precocious element III + TX, amidophos + TX, thiophanate Ling+TX, prochloraz+TX, chloranil+TX, procymidone+TX, profluthrin+TX, fluthrin+TX, cypermethrin+TX, fenthrin+TX, propamocarb+TX, propiconazole+TX, methyl propineb+TX, propoxur+TX, propyl isomer+TX, iodoquinoxaline+TX, ethiazole+TX, prothioconazole+TX, prothiophos+TX, fluopicolide+TX, pyraclostrobin+TX, pyraclostrobin+TX, pyraclostrobin+TX, pyraclostrobin+TX, pyraclostrobin+TX, bifenthrin+TX, pyraclostrobin+TX, anti-pyrethrin+TX, pyrethrin I+TX, pyrethrin II+TX, pyrethrin+TX, pyraclostrobin+TX, fluopicolide+TX, pyraclostrobin+TX, Pyridine-4-amine + TX, pyrimidine oxime + TX, pyrimethanil + TX, pyrimethanil + TX, pyrimethanil + TX, rodenticide + TX, benpyraclostrobin + TX, pyraclostrobin + TX, pyraclostrobin + TX, pyraclostrobin + TX, quassia extract + TX, quinalphos + TX, quinalphos-methyl + TX, algaquinone + TX, fluquinoxaline + TX, quinone + TX, oxazolidinone + TX, quinalphos + TX, pentachloronitrobenzene + TX, R-1492 + TX, iodine + TX, resfurothrin + TX, giant knotweed extract + TX, ribavirin + TX, R-metalaxyl + TX, rotenone + TX, ryanodine + TX, rianodine + TX, S421 + TX, sabah Veratrum + TX, octamethoxazole + TX, sea Onion glycoside + TX, cintamidine + TX, clomiphene carboxamide + TX, selamidin + TX, selamidin + TX, selamidin + TX, selamidin + TX, sodium arsenite + TX, sodium cyanide + TX, sodium fluoride + TX, sodium fluoroacetate + TX, sodium hexafluorosilicate + TX, sodium pentachlorophenol + TX, sodium selenate + TX, sodium tetrathiocarbonate + TX, sodium thiocyanate + TX, thionyl + TX, banana corm weevil attractant + TX, spiroxamin + TX, SSI-121 + TX, hairy mosquito nematode + TX, small roll moth nematode + TX, noctuid nematode + TX, Grizzli nematode + TX, sharp nematode + TX,Steinernema riobravis + TX, Steinernema gryllotalpa + TX, Steinernema species + TX, streptomycin + TX, streptomycin sesquisulfate + TX, strychnine + TX, methyl eugenol + TX, sulfosulfuron + TX, sulfosulfuron sodium + TX, sulfiram + TX, sulfluramid + TX, thiotepa + TX, sulfoxide + TX, sulfur + TX, sulfuryl fluoride + TX, sulprofos + TX, tar + TX, tau-fluvalinate + TX, buprofezin + TX, TDE + TX, tebuconazole + TX, isobutyl ethylacridine + TX, butyl pyrimiphos + TX, tetrachlorophthalodinitrile + TX, temephos + TX, tebutam + TX, TEPP + TX, allethrin + TX, bendiocarb + TX, N-tert-butyl-N-[6-[[[(1-methyltetrazol-5-yl)phenylmethylene]amino]oxymethyl]-2-pyridinyl]carbamate + TX, tetrachloroethane + TX, tetrachlorothiophene + TX, fluquinconazole + TX, tetradec-11-en-1-yl acetate + TX, tetradifon + TX, tetramethrin + TX, binapacryl + TX, thallium sulfate + TX, thiabendazole + TX, thiafenox + TX, thipronitrile + TX, thichlorphon + TX, thifluzamide + TX, pirimicarb + TX, cartap + TX, cartap oxalate + TX, thiodiazole copper + TX, monocrotophos + TX, phosfolan + TX, thiomersal + TX, malathion + TX, thionazin + TX, thiophanate + TX, thiophanate-methyl + TX, chlorbenside + TX, monosultap + TX, monosultap sodium + TX, thiotepp + TX, selamectin + TX, thuringiensin + TX, tiadinil + TX, tolclofos-methyl + TX, tralomethrin + TX, tolylfluanid + TX, tralomethrin + TX, transfluthrin + TX, triticonazole + TX, triadimefon + TX, triadimenol + TX, triazophos + TX, imidacloprid + TX, triazamate + TX, tributyltin oxide + TX, isopropyrophos-3 + TX, bromophos-ethyl + TX, Trichogramma species + TX, picoxystrobin + TX, tricyclazole + TX, tridemorph + TX, niclosamide + TX, trichlorfon + TX, trifloxystrobin + TX, fludioxonil + TX, azoxystrobin + TX, Mediterranean fruit fly attractant + TX, Mediterranean fruit fly attractant A + TX, Mediterranean fruit fly attractant B1 + TX, Mediterranean fruit fly attractant B2 + TX, Mediterranean fruit fly attractant C + TX, dimecron + TX, trichomycin + TX, trinexapac-ethyl + TX, triphenyltin acetate + TX, triphenyltin hydroxide + TX, methoprene + TX, triticonazole + TX, trunc-call + TX, western predatory mite + TX, urethane imine + TX, validamycin + TX, valifenalate + TX, formetanate + TX, ethiprole + TX, veratridine + TX, veratrine + TX, piperonyl butoxide + TX, Verticillium lecanii + TX, vinclozolin + TX,Warfarin + TX, XMC + TX, Xylenol + TX, Zeatin + TX, Zetamethrin + TX, Zhongshengmycin + TX, Zinc Naphthenate + TX, Zinc Phosphide + TX, Thiazole Zinc + TX, Zineb + TX, Ziram + TX, Oxamiphos + TX, Zoxamide + TX, α-(1,1-Dimethylethyl)-α-[4'-(Trifluoromethoxy)[1,1'-Biphenyl]-4-yl]-5-Pyrimidinemethanol + TX;;

[0313] Typhula phacorrhiz Strain 94670 + TX, Acinetobacter lwoffii + TX, Acremonium sp. + TX, Acremonium chrysogenum + TX, Acremonium diospyri + TX, Acremonium obclavatum + TX, Adoxophyes orana Granulovirus (AdoxGV) + TX, Agrobacterium radiobacter Strain K84 + TX, Alternaria sp. + TX, Alternaria cassiae + TX, Alternaria destruens + TX, Ampelomyces quisqualis + TX, Aspergillus flavus AF36 + TX, Aspergillus flavus NRRL 21882 + TX, Aspergillus sp. + TX, Aureobasidium pullulans + TX, Azospirillum ([[]] + TX, TAZO ) + TX, Azotobacter + TX, Azotobacter chroococcum + TX, Azotobacter cystogenes (BionaturalBlooming ) + TX, Bacillus amyloliquefaciens + TX, Bacillus cereus + TX, Bacillus chitinovorans Strain AQ746 + TX, Bacillus chitinovorans Strain CM-1 + TX, Bacillus circulans + TX, Bacillus firmus ([[]] + TX, ) especially Strain CNMC 1-1582 (e.g., from BASF SE) ) + TX, Bacillus licheniformis Strain 3086 ([[]] + TX, Green ) + TX, Bacillus licheniformis Strain HB-2 (Biostart TM , formerly known as ) + TX, Bacillus macerans + TX, Bacillus marismortui + TX, Bacillus megaterium + TX, Bacillus mycoides Strain AQ726 + TX, Bacillus popilliae (Milky Spore )+TX, Bacillus pumilus species+TX, Bacillus pumilus strain AQ717+TX, Bacillus pumilus strain GB34 (Yield )+TX, Bacillus pumilus strain QST 2808( +TX, Ballad )+TX, Bacillus sphaericus +TX, Bacillus species+TX, Bacillus strain AQ175+TX, Bacillus strain AQ177+TX, Bacillus strain AQ178+TX, Bacillus subtilis strain AQ153+TX, Bacillus subtilis strain AQ743+TX, Bacillus subtilis strain QST 713( +TX, +TX, )+TX, Bacillus subtilis strain QST 714 +TX, Bacillus subtilis strain QST3002+TX, Bacillus subtilis strain QST3004+TX, Bacillus amyloliquefaciens var. strain FZB24( +TX, )+TX, Bacillus thuringiensis aizawai GC91 +TX, Bacillus thuringiensis Cry 2Ae+TX, Bacillus thuringiensis Cry1Ab+TX, Bacillus thuringiensis israelensis( +TX, +TX, )+TX, Bacillus thuringiensis kurstaki( +TX, +TX, +TX, +TX, Scutella +TX, Turilav +TX, +TX, Dipel +TX, +TX, )+TX, Bacillus thuringiensis kurstaki BMP 123 +TX, Bacillus thuringiensis kurstaki HD-1 (Bioprotec-CAF / )+TX, Bacillus thuringiensis strain AQ52+TX, Bacillus thuringiensis strain BD#32+TX, Bacillus thuringiensis tenebrionis( +TX, BtBooster)+TX, Bacillus thuringiensis aizawai var.( +TX, )+TX, Bacterial species( +TX, +TX, )+TX, a phage of Clavipacter michiganensis +TX, )+TX, Beauveria bassiana +TX, Brocaril )+TX, Beauveria bassiana GHA (Mycotrol +TX, Mycotrol +TX, )+TX, Beauveria brongniartii +TX, Schweizer +TX, )+TX, Beauveria species +TX, Botrytis cinerea +TX, Bradyrhizobium japonicum +TX, Bacillus brevis +TX, Burkholderia cepacia +TX, +TX, Blue )+TX, Burkholderia +TX, Burkholderia gladioli +TX, Burkholderia species +TX, Cirsium arvense fungus (CBH Canadian )+TX, Candida casei +TX, Candida famata +TX, Candida fructus +TX, Candida glabrata +TX, Candida guilliermondii +TX, Candida kefyr +TX, Candida oleophila strain O +TX, Candida parapsilosis +TX, Candida pelliculosa +TX, Candida pulcherrima +TX, Candida rugosa +TX, Candida saitoi +TX, )+TX, Candida sake +TX, Candida species +TX, Candida tenuis +TX, CDC group DF-2 +TX, Cellulomonas flavigena +TX, Chaetomium spirale +TX, Chaetomium globosum +TX, Janthinobacterium lividum strain PRAA4-1T +TX, Cladosporium cladosporioides +TX, Cladosporium cladosporioides f. sp. cucumerinum +TX, Cladosporium oxysporum +TX, Cladosporium species +TX, Cladosporium tenuissimum +TX, Gliocladium roseum +TX, Colletotrichum acutatum +TX, Coniothyrium minitans (Cotans )+TX, Coniothyrium species +TX, Cryptococcus albidus +TX, Cryptococcus terreus +TX, Cryptococcus infirmo-miniatus +TX, Cryptococcus laurentii +TX, Epiphyas postvittana granulovirus +TX, Cupriavidus campinensis+TX, Cydia pomonella granulovirus( +TX, +TX, Plus+TX, Madex Max+TX, +TX, Cylindrobasidium laeve +TX, Cladosporium+TX, Debaryomyces hansenii+TX, Drechslera hawaiinensis+TX, Enterobacter cloacae+TX, Enterobacteriaceae+TX, Entomophthora virulenta +TX, Epicoccum+TX, Epicoccum nigrum+TX, Epicoccum sp.+TX, Filobasidium floriforme+TX, Fusarium acuminatum+TX, Fusarium chlamydosporum+TX, Fusarium oxysporum( +TX, Biofox )+TX, Fusarium proliferatum+TX, Fusarium sp.+TX, Geotrichum candidum+TX, Gliocladium catenulatum +TX, )+TX, Gliocladium roseum+TX, Gliocladium sp. +TX, Gliocladium virens +TX, granulovirus +TX, Halobacillus halophilus+TX, Halobacillus oncorhynchi+TX, Halobacillus trueperi+TX, Halomonas sp.+TX, Halomonas subglaciescola+TX, Halovibrio variabilis+TX, Hanseniaspora uvarum+TX, Helicoverpa armigera nucleopolyhedrovirus +TX, Helicoverpa zea nucleopolyhedrovirus +TX, Isaria fumosorosea (formerly known as Paecilomyces fumosoroseus strain+TX, +TX, )+TX, Isoflavone formononetin +TX, Kluyveromyces lemonis+TX, Kluyveromyces sp.+TX, Leptolegnia caudata +TX, Lecanicillium lecanii (formerly known as strain KV01 (e.g., of Koppert / Arysta's ) of Verticillium lecanii Conidia+TX, Lecanicillium longisporum +TX, Lecanicillium muscarium +TX, Lymantria dispar multicapsid nucleopolyhedrovirus +TX, Halococcus salifodinae +TX, Melarhaphe groenlandica +TX, Metarhizium anisopliae (Destruxin )+TX, Metarhizium anisopliae +TX, Metschnikowia fruticola +TX, Metschnikowia pulcherrima +TX, Microdochium dimerum +TX, Micromonospora aurantiaca +TX, Microsphaeropsis ochracea +TX, Muscodor albus 620 +TX, Muscodor roseus, especially strain A3-5 (accession number NRRL 30548) +TX, mycorrhizal species( +TX, Root )+TX, Myrothecium verrucaria strain AARC-0255( +TX, BROS )+TX, Ophiostoma piliferum strain D97 +TX, Paecilomyces farinosus +TX, Paecilomyces lilacinus strain 251 (MeloCon )+TX, Paecilomyces lilacinus (Biostat )+TX, Paenibacillus polymyxa +TX, Pantoea agglomerans (BlightBan )+TX, Pantoea species +TX, Pasteuria penetrans, especially strain Pn1 (CLARIVA from Syngenta / ChemChina) +TX, +TX, Pasteuria species +TX, Penicillium ochrochloron +TX, Penicillium byssinum( +TX, )+TX, Penicillium brevicompactum +TX, Penicillium frequentans +TX, Penicillium griseofulvum +TX, Penicillium purpurogenum +TX, Penicillium species +TX, Penicillium viridicatum +TX, Wolfiporia cocos +TX, phosphate solubilizing bacteria +TX, Phytophthora cryptogea +TX, Phytophthora palmivora +TX, Pichia anomala +TX, Pichia guilliermondii +TX, Pichia membranaefaciens +TX, Pichia onychis +TX, Pichia stipites +TX, Pseudomonas aeruginosa +TX, Pseudomonas aureofasciens (Spot-Less ) +TX, Pseudomonas cepacia +TX, Pseudomonas chlororaphis +TX, Pseudomonas corrugate +TX, Pseudomonas fluorescens strain A506 (BlightBan ) +TX, Pseudomonas putida +TX, Pseudomonas reactans +TX, Pseudomonas spp. +TX, Pseudomonas syringae +TX, Pseudomonas viridiflava +TX, Pseudomonas fluorescens +TX, Pseudozyma flocculosa strain PF-A22UL (Sporodex ) +TX, Puccinia canaliculata +TX, Puccinia thlaspeos (Wood ) +TX, Pythium paroecandrum +TX, Pythium oligandrum ( +TX, ) +TX, Pythium periplocum +TX, Rhanella aquatilis +TX, Rhanella spp. +TX, Rhizobia ( +TX, )+TX, Rhizoctonia+TX, Rhodococcus globerulus strain AQ719+TX, Rhodosporidium diobovatum+TX, Rhodosporidium toruloides+TX, Rhodotorula glutinis+TX, Rhodotorula graminis+TX, Rhodotorula mucilagnosa+TX, Rhodotorula rubra+TX, Rhodotorula spp.+TX, Saccharomyces cerevisiae+TX, Salinococcus roseus+TX, Sclerotinia minor+TX, Sclerotinia minor +TX, Scytalidium spp.+TX, Scytalidium uredinicola+TX, Serratia marcescens+TX, Serratia plymuthica+TX, Serratia spp.+TX, Sordaria fimicola+TX, Spodoptera exigua nucleopolyhedrovirus( +TX, )+TX, Spodoptera littoralis nucleopolyhedrovirus +TX, Sporobolomyces roseus+TX, Stenotrophomonas maltophilia+TX, Streptomyces hygroscopicus+TX, Streptomyces albaduncus+TX, Streptomyces exfoliates+TX, Streptomyces galbus+TX, Streptomyces griseoplanus+TX, Streptomyces griseoviridis +TX, Streptomyces lydicus +TX, Streptomyces lydicus WYEC-108 +TX, Streptomyces violaceus +TX, Tilletiopsis minor +TX, Tilletiopsis spp. +TX, Trichoderma asperellum (T34 )+TX, Trichoderma atroviride +TX, Trichoderma gamsii +TX, Trichoderma hamatum TH 382 +TX, Trichoderma harzianum rifai +TX, Trichoderma harzianum T-22( +TX, PlantShield +TX, +TX, )+TX, Trichoderma harzianum T-39 +TX, Trichoderma inhamatum +TX, Trichoderma koningii +TX, Trichoderma lignorum +TX, Trichoderma longibrachiatum +TX, Trichoderma polysporum (Binab )+TX, Trichoderma spp. LC 52 +TX, Trichoderma taxi +TX, Trichoderma virens +TX, Trichoderma virens (formerly Gliocladium virens GL-21)(Soil )+TX, Trichoderma viride +TX, Trichoderma viride strain ICC 080 +TX, Trichosporon pullulans+TX, Trichosporon spp.+TX, Trichothecium roseum+TX, Trichothecium spp.+TX, Typhula phacorrhiza strain 94671+TX, Ulocladium atrum+TX, Ulocladium oudemansii( )+TX, Ustilago maydis+TX, various bacteria and supplementary nutrients (Natural )+TX, various fungi (Millennium )+TX, Verticillium chlamydosporium+TX, Vip3Aa20 +TX, Virgibaclillus marismortui+TX, Xanthomonas campestris pv. Poae +TX, Xenorhabdus bovienii+TX, Photorhabdus nematophila+TX;

[0314] Azadirachtin (Plasma Neem +TX、 +TX、 +TX、 e.g., AZATIN XL) from Certis, US)+TX, plant IGR( +TX、 )+TX, canola oil (Lilly Miller )+TX, Chenopodium ambrosioides near ambrosioides +TX, chrysanthemum extract +TX, essential oil of Labiatae +TX, neem oil extract +TX, clove - rosemary - peppermint and thyme oil extract (Garden insect )+TX, garlic+TX, betaine +TX, kaolin +TX, lemongrass oil +TX, Melaleuca alternifolia extract (also known as tea tree oil) (Timorex )+TX, clove - peppermint - garlic oil and mint mixture (Soil )+TX, clove - rosemary and peppermint extract mixture (EF )+TX, rosemary - sesame - peppermint - thyme and cinnamon extract mixture (EF )+TX, neem oil+TX, catnip (Nepeta cataria) (catnip oil)+TX, Nepeta catarina+TX, nicotine+TX, oregano oil +TX, Pedaliaceae oil +TX, pine oil +TX, pyrethrum+TX, Quillaja saponaria +TX, Reynoutria japonica Houtt. +TX, )+TX, rotenone (Eco )+TX, Rutaceae plant extract +TX, soybean oil (Ortho )+TX, storage glucan of brown algae +TX, thyme oil( MMF+TX, )+TX;

[0315] (E,Z)-7,9 - dodecadien - 1 - yl acetate+TX, (E,Z,Z)-3,8,11 - tetradecatrienyl acetate+TX, (Z,Z,E)-7,11,13 - hexadecatrienal+TX, 2 - methyl - 1 - butanol+TX, +TX, blackheaded fireworm pheromone (3M SprayableBlackheaded Fireworm )+TX, calcium acetate+TX, +TX, codling moth pheromone (Paramount dispenser-(CM) / Isomate )+TX, Entostat powder (extract from palm tree) (Exosex )+TX, grape leafroller pheromone (3M MEC - GBM Sprayable )+TX, lavandulic acid ester+TX, leafroller pheromone (3M MEC - LR Sprayable ) + TX, Musca domestica pheromone (Snip7Fly + TX, Grapholita molesta pheromone (3M orientalfruit mothsprayable ) + TX, Synanthedon exitiosa pheromone + TX, + TX, Starbar PremiumFly ) + TX, Tuta absoluta pheromone (3M Sprayable ) + TX;

[0316] Fopius arisanus + TX, Acerophagus papaya + TX, Adalia bipunctata + TX, Adalia bipunctata + TX, Adalia bipunctata + TX, Glyptapanteles sp., Copidosoma sp., Amblyseius andersoni( + TX, ) + TX, Amblyseius californicus( + TX, ) + TX, Amblyseius cucumeris + TX, Bugline ) + TX, Amblyseius fallacis + TX, Amblyseius swirskii (Bugline + TX, ) + TX, Amblyseius oudemansi + TX, Encarsia sp., Eupelmus urozonus, Anagyrus sp., Anagyrus kamali, Anagyrus loecki, Anagyrus pseudococci + TX, Ceroplastes rubens, Nasonia sp., Anthocoris nemoralis + TX, Aphelinus abdominalis( + TX, ) + TX + TX, Aphelinus asychis, Lysiphlebus sp + TX, Aphidius ervi( ) + TX, Aphidius ervi + TX, Aphidius gifuensis, Aphidius persicae + TX, Aphidoletes aphidimyza( + TX, ) +TX, Aphytis lingnanensis +TX, Aphytis indica +TX, Aprostocetus hartigii +TX, Paederus fuscipes +TX, Bombus species +TX, Bombus terrestris ( +TX, ) +TX, Bombus terrestris (Natupol ) +TX, Cephalonomia stephanoderis +TX, Chilocorus rubidus +TX, Chrysopa carnea ( +TX, ) +TX, Chrysopa erythromma +TX, Cirrospilus ingenus +TX, Cirrospilus species +TX, Closterocerus chamaeleon +TX, Closterocerus species +TX, Coccidoxenoides perminutus +TX, Aphelinus mali +TX, Aphelinus asychis +TX, Cotesia flavipes +TX, Cotesia plutellae +TX, Cryptolaemus montrouzieri +TX, ) +TX, Cybocephalus niponicus +TX, Dacnusa sibirica +TX, +TX, ) +TX, Delphastus catalinae +TX, Delphastus pusillus +TX, Diachasmimorpha krausii +TX, Doryctobracon longicaudatus +TX, Diaparsis jucunda +TX, Encarsia alegrensis +TX, Dacnusa sibirica +TX, +TX, ) +TX, Ceranisus species +TX, Coccophagus longulus +TX, Encarsia ( +TX, +TX, ) +TX, Encarsia guadeloupae +TX, Encarsia haitensis +TX, Sphaerophoria scripta +TX, Eretmocerus siphonini +TX, Eretmocerus californicus +TX, Eretmocerus species +TX, +TX, Eretline +TX, ) +TX, Eretmocerus hayati +TX, Eretmocerus montrouzieri +TX, Eretline ) +TX, Eretmocerus siphonini +TX, Stethorus punctillum +TX, Cecidomyia acarivorax +TX, Cecidomyia acarivorax +TX, Fopius ceratitivorus +TX, Formononetin (Wirless ) +TX, Thrips abdominalis +TX, Typhlodromus occidentalis +TX, Rhinocyllus lecontei +TX, Habrobracon hebetor +TX, Harmonia axyridis +TX, Heterorhabditis sp. (NemaShield +TX, +TX, +TX, +TX, +TX, +TX, +TX, ) +TX, Heterorhabditis megidis (Nemasys +TX, BioNem +TX, Exhibitline +TX, ) +TX, Heterorhabditis sp. (Lawn ) +TX, Coelophora saucia +TX, Hypoaspis aculeifer +TX, ) +TX, Hypoaspis miles +TX, ) +TX, Ganaspis brasiliensis +TX, Lecanoideus floccissimus +TX, Lemophagus errabundus +TX, Trichopria drosophilae +TX, Encarsia citrina +TX, Anagyrus sp. +TX, Lindorus lophanthae +TX, Lipolexis oregmae +TX, Lucilia sericata +TX, Lysiphlebus testaceipes +TX, Miridae +TX, Macroline +TX, ) +TX, Mesoseiulus longipes +TX, Microterys flavus +TX, Metaphycus lounsburyi +TX, Micromus angulatus +TX, Microterys ericeri +TX, Muscidifurax raptorellus and Spalangia cameroni +TX, Neodryinustyphlocybae+TX, Neoseiulus californicus+TX, Neoseiulus cucumeris +TX, Pseudoseiulus+TX, Nesideocoris tenuis( +TX, )+TX, Hydrotaea aenescens +TX, Orius sauteri( +TX, Oriline )+TX, Orius laevigatus( +TX, Oriline )+TX, Orius majusculus(Oriline )+TX, Orius strigicollis( )+TX, Pauesia juniperorum+TX, Pediobius foveolatus+TX, Phasmarhabditis hermaphrodita +TX, Phymastichus coffea+TX, Phytoseiulus setifer+TX, Phytoseiulus persimilis( +TX, Phytoline )+TX, Podisus maculiventris +TX, Pseudacteon curvatus+TX, Pseudacteon obtusus+TX, Pseudacteon tricuspis+TX, Pseudaphycus maculipennis+TX, Pseudleptomastix mexicana+TX, Trichopoda pennipes+TX, Therophilus spp.(complex)+TX, Syntomopus spp.+TX, Rhyzobius lophanthae+TX, Rodolia cardinalis+TX, Rumina decollate+TX, Semielacher petiolatus+TX, Sitobion avenae +TX, Steinernema carpocapsae(Nematac +TX, +TX, BioNem +TX, +TX, +TX, )+TX, Steinernema feltiae +TX, Nemasys +TX, BioNem +TX, +TX, +TX, +TX, Exhibitline +TX, +TX, )+TX, sawfly nematode (Nemasys +TX, BioNem +TX, Exhibitline )+TX, Steinernema feltiae( +TX, )+TX, Steinernema gryllotalpae (Nematac )+TX, Steinernema species +TX, Steinernematidae species (Guardian )+TX, Stethorus punctillum +TX, Encarsia formosa +TX, Tetrastichus setifer +TX, Thripobius semiluteus +TX, Torymus sinensis +TX, Trichogramma brassicae (Tricholine )+TX, Trichogramma brassicae +TX, Trichogramma evanescens +TX, Trichogramma minutum +TX, Trichogramma ostriniae +TX, Trichogramma lativentre +TX, Trichogramma pretiosum +TX, Xanthopimpla stemmator +TX;

[0317] Abscisic acid +TX, +TX, +TX, +TX, silver leaf fungus (Chondrostereum purpureum) (Chontrol )+TX, Colletotrichum gloeosporioides +TX, copper octanoate +TX, δ trap (Delta trap) (Trapline )+TX, Erwinia amylovora (Harpin)( +TX, Ni-HIBIT Gold )+TX, fatty acids from natural by-products derived from extra-virgin olive oil +TX, ferric phosphate +TX, funnel trap (Funneltrap) (Trapline )+TX, +TX, Grower's +TX, homobrassinolide +TX, ferric phosphate (Lilly Miller Worry Free FerramolSlug&Snail ) + TX, MCP hail trap (Trapline ) + TX, parasitic insect Microctonus hyperodae + TX, Mycoleptodiscus terrestris + TX, Semaspore Organic Grasshopper ) + TX, Thripline ) + TX, potassium bicarbonate + TX, potassium iodide + potassium thiocyanate + TX, potassium salt of fatty acid + TX, potassium silicate solution + TX, spider venom + TX, Trapline + TX, Rebell ) + TX, + TX, Takitrapline y + ) + TX, + TX;

[0318] Bacillus mojavensis strain R3B (registration number NCAIM(P)B001389) (WO 2013 / 034938) from Certis USA LLC, Bacillus pumilus + TX, especially strain BU F - 33 + TX, having NRRL registration number 50185 (from BASF + TX, EPA registration number 71840 - 19) + TX, Bacillus subtilis CX - 9060 from Certis USA LLC, Bacillus species + TX, especially strain D747 (available from Kumiai Chemical Industry Co., Ltd. + TX as DOUBLE obtained) + TX, having registration number FERM BP - 8234 + TX, US Patent No. 7,094,592 + TX, Bacillus subtilis strain BU1814 + TX, (from BASF SE PLUS + TX, FLEX and EXTRA) + TX, Bacillus amyloliquefaciens var. strain FZB24, having registration number DSM 10271 (available from Novozymes or ECO Acquisition (EPA registration number 70127-5)) + TX, Bacillus subtilis + TX, especially strain QST713 / AQ713 (having NRRL accession number B-21661 and described in U.S. Patent No. 6,060,051 + TX, available from Bayer CropScience LP in the United States + TX as OPTI or ASO Acquisition) + TX, Paenibacillus polymyxa + TX, especially strain AC-1 (e.g., from Green Biotech Company Ltd. ) + TX, Paenibacillus sp. strain with accession number NRRL B-50972 or accession number NRRL B-67129 + TX, WO 2016 / 154297 + TX, Pantoea agglomerans + TX, especially strain E325 (accession number NRRL B-21856) (available from Northwest AgriProducts as BLOOMTIME BIOLOGICAL TM FDBIOPESTICIDE Acquisition) + TX, Pseudomonas proradix (e.g., from Sourcon Padena ) + TX;

[0319] Aureobasidium pullulans + TX, especially blastospores of strain DSM14940 + TX, blastospores of strain DSM 14941 or a mixture of blastospores of strains DSM14940 and DSM14941 (e.g., + TX from bio-ferm in Switzerland and BLOSSOM ) + TX, Pseudozyma aphidis (as disclosed by Yissum Research Development Company of the Hebrew University of Jerusalem in WO 2011 / 151819) + TX, Saccharomyces cerevisiae + TX, especially strains CNCM No. 1-3936 + TX, CNCM No. 1-3937 + TX, CNCM No. 1-3938 or CNCM No. 1-3939 from Lesaffre et Compagnie (WO 2010 / 086790) + TX;

[0320] Bacteria including: Agrobacterium radiobacter strain K84 (e.g., from AgBioChem in California ) + TX, Bacillus amyloliquefaciens isolate B246 (e.g., AVOGREEN from the University of Pretoria) TM ) + TX, Bacillus amyloliquefaciens strain F727 (also known as strain MBI110) (NRRL accession number B - 50768 + TX, WO 2014 / 028521) (from Marrone BioInnovations) ) + TX, Bacillus amyloliquefaciens strain FZB42 + TX, accession number DSM 23117 (available from ABiTEP GmbH in Germany) obtainable)+TX, Bacillus amyloliquefaciens+TX, especially strain D747 (available from Combined Chemical Industries as Double Nickel TM obtainable + TX, with accession number FERM BP - 8234 + TX, U.S. Patent No. 7,094,592)+TX, Bacillus licheniformis FMCH001 and Bacillus subtilis FMCH002 (from FMC Corporation) (WG) and (WP))+TX, Bacillus licheniformis+TX, especially strain SB3086+TX, with accession number ATCC 55406+TX, WO 2003 / 000051 (available from Novozymes as biopesticide and GREEN RELEAF TM obtainable)+TX, Bacillus methylotrophicus strain BAC - 9912 (from the Chinese Academy of Sciences' Institute of Applied Ecology)+TX, Bacillus mycoides+TX, isolate+TX, with accession number B - 30890 (available from Certis USA as BMJ or WG and LifeGard TM obtainable)+TX, Bacillus pumilus+TX, especially strain GB34 (available from Bayer AG in Germany as Yield obtainable)+TX, Bacillus pumilus+TX, especially strain QST2808 (available from Bayer CropScience LP in the United States as Obtained +TX, with accession number NRRL B-30087 and described in U.S. Patent No. 6,245,551 +TX, Bacillus subtilis CX-9060 from Certis USA LLC, Bacillus subtilis IAB / BS03 (AVIV from STK Bio-Ag Technologies TM +TX, from Idai Nature ) +TX, Bacillus subtilis KTSB strain (from Donaghys ) +TX, Bacillus subtilis strain BU1814 +TX, (available from BASF SE as PLUS +TX, FLEX and EXTRA obtained) +TX, Bacillus subtilis strain GB03 (available from Bayer AG +TX as obtained) +TX, Bacillus subtilis strain MBI 600 (available from BASF SE as SUBTILEX) +TX, with accession number NRRL B-50595 +TX, U.S. Patent No. 5,061,495 +TX, Bacillus subtilis strain Y1336 (available from Bion-Tech in Taiwan, China +TX as WP obtained, registered as a biopesticide in Taiwan, China under accession numbers 4764 +TX, 5454 +TX, 5096 and 5277) +TX, Bacillus amyloliquefaciens var. strain FZB24, with accession number DSM 10271 (available from Novozymes as or ECO obtained (EPA registration number 70127-5)) +TX, Bacillus subtilis Y1336 (available from Bion-Tech in Taiwan, China +TX as WP obtained, as a biofungicide registered in Taiwan under registration numbers 4764+TX, 5454+TX, 5096 and 5277)+TX, Paenibacillus epiphyticus from BASF AG (WO 2016 / 020371)+TX, Paenibacillus polymyxa plantarum species from BASF AG (WO 2016 / 020371)+TX, Paenibacillus species strains with registration number NRRL B-50972 or registration number NRRLB-67129+TX, WO 2016 / 154297+TX, Pseudomonas chlororaphis strain AFS009+TX, with registration number NRRL B-50897+TX, WO 2017 / 019448 (e.g. +TX, HOWLER from AgBiome Innovations, USA)+TX TM and )+TX, Pseudomonas chlororaphis+TX, in particular strain MA342 (e.g. from Bioagri and Koppert) +TX, +TX and )+TX, Pseudomonas fluorescens strain A506 (e.g. from NuFarm) A506) + TX, Pseudomonas proradix (e.g. from Sourcon Padena )+TX, Streptomyces glaucum strain K61 (also known as Streptomyces flavoscens strain K61) (accession number DSM7206) (from Verdera +TX, from BioWorks +TX, see Crop Protection 2006 +TX, 25 +TX, 468-475) +TX, Streptomyces lydicus strain WYEC108 (also known as Streptomyces lydicus strain WYCD108US) (from Novozymes and )+TX;

[0321] Trichoderma aureum strain T11 (IMI352941 / CECT20498) +TX, Pseudomonas graminearum strain AQ10 +TX, with accession number CNCM 1-807 (e.g. +TX, AQ from IntrachemBioItalia )+TX, Pseudomonas aeruginosa+TX, in particular strain AQ 10 (e.g. AQ from Intrachemica Biologica Italia ) + TX, Aspergillus flavus strain NRRL 21882 (as a known product from Syngenta / ChemChina Group) ) + TX, Aureobasidium pullulans + TX, especially blastospores of strain DSM 14941 + TX, Aureobasidium pullulans + TX, especially blastospores of strain DSM14940 + TX, Aureobasidium pullulans + TX, especially a mixture of blastospores of strains DSM14940 and DSM 14941 (e.g., from Biocontrol - Phytopharm SA) ) + TX, Chaetomium cupreum (registration number CABI 353812) (e.g., BIOKUPRUM from AgriLife) TM ) + TX, Chaetomium globosum (available from Rivale) ) + TX, Cladosporium cladosporioides + TX, strain H39 + TX, with registration number CBS122244 + TX, US2010 / 0291039 (by Stichting Dienst Landbouwkundig Onderzoek) + TX, Coniothyrium minitans + TX, especially strain CON / M / 91 - 8 (registration number DSM9660 + TX, e.g., from Bayer CropScience Biologics) ) + TX, Cryptococcus flavescens + TX, strain 3C (NRRL Y - 50378) + TX + TX, Dactylaria candida + TX, Dilophosphora alopecuri (available from TWIST) ) + TX, Fusarium oxysporum + TX, strain Fo47 (available from Natural Plant Protection) ) + TX, Gliocladium catenulatum (synonym: Gliocladium roseum) strain J1446 (e.g., from Lallemand) )+TX, pink Glioma (also known as pink spiral polyspore mold (Clonostachys rosea f rosea)) strain IK726 (Jensen DF+TX et al. Development of a biocontrol agent for plant disease control with special emphasis on the near commercial fungal antagonist Clonostachys rosea strain'IK726' [Special emphasis on the development of biological control agents for plant disease control of the near commercial fungal antagonist pink Glioma strain'IK726']+TX, Australasian Plant Pathol [Australian Plant Pathology]. 2007, 36(2):95-101)+TX, pink Glioma (also known as pink spiral polyspore mold)+TX, especially strain 321U from Adjuvants Plus+TX, strain ACM941, such as Xue AG.+TX disclosed in (Efficacy of Clonostachys rosea strain ACM941 and fungicide seed treatments for controlling the root tot complex of field pea [Efficacy of Clonostachys rosea strain ACM941 and fungicide seed treatments for controlling the root tot complex of field pea] +TX, Can Jour Plant Sci [Canadian Journal of Plant Science] 2003 +TX, 83(3):519-524), Metschnikowia fructicola +TX, in particular strain NRRL Y-30752 +TX, Microsphaeropsis ochracea +TX, Penicillium steckii from BASF AG (DSM 27859 +TX, WO 2015 / 067800) +TX, Trichoderma aculeatus strain ICC 012 (also known as Trichoderma harzianum ICC012) +TX, having registration number CABI CC IMI 392716 and Trichoderma gamsii (originally Trichoderma viride) strain ICC 080+TX, a mixture with accession number IMI 392151 (e.g. +TX, BIO-TAM™ from Isagro USA, Inc. +TX or from AgrobiosoldeMexico, SA de CV) +TX. )+TX, Penicillium vermiculatum+TX, Phlebiopsis gigantea strain VRA 1992 (from Danstar Ferment C) +TX, Pseudozyma flocculosa +TX, strain PF-A22UL (available from Plant Products Co., California) +TX L) + TX, cell wall of Saccharomyces cerevisiae strain LAS117 (from Lesaffre +TX, from BASF AG ) +TX, Saccharomyces cerevisiae strains CNCM No. 1-3936+TX, CNCM No. 1-3937+TX, CNCM No. 1-3938+TX, CNCM No. 1-3939 (WO 2010 / 086790)+TX, from Lesaffre, France+TX, Saccharomyces cerevisiae+TX, especially strain LASO2 (from Agro-Levures et Dérivés)+TX, Simplicillium lanosoniveum+TX, strain T34 (e.g., T34 from Biocontrol Technologies S.L., Spain)+TX or strain ICC012 from Isagro+TX, strain WRL-076 (NRRL Y-30842)+TX, U.S. Patent No. 7,579,183+TX, Talaromyces flavus+TX, strain V117b+TX, Trichoderma asperelloides JM41R (accession number NRRL B-50759) (TRICHO from BASF SE ) +TX, Trichoderma asperellum+TX, especially strain SKT-1+TX, with accession number FERM P-16510 (e.g., from Combinatorial Chemical Industries ) + TX, Trichoderma asperellum + TX, especially + TX strain kd (such as T-Gro from Andermatt Biocontrol), Trichoderma atroviride strain 77B (T77 from Andermatt Biocontrol), Trichoderma atroviride strain ATCC 20476 (IMI 206040), Trichoderma atroviride strain LC52 (such as Tenet from Agrimm Technologies Limited), Trichoderma atroviride strain LU132 (such as Sentinel from Agrimm Technologies Limited), Trichoderma atroviride strain NMI No. V08 / 002388, Trichoderma atroviride strain NMI No. V08 / 002389, Trichoderma atroviride strain NMI No. V08 / 002390, Trichoderma atroviride strain No. V08 / 002387, Trichoderma atroviride strain SKT-1 (FERM P-16510), Japanese Patent Application (Kokai) 11-253151A, Trichoderma atroviride strain SKT-2 (FERM P-16511), Japanese Patent Application (Kokai) 11-253151A, Trichoderma atroviride strain SKT-3 (FERM P-17021), Japanese Patent Application (Kokai) 11-253151A, Trichoderma atroviride + TX, especially strain SC1 (registration number CBS122089 + TX, WO 2009 / 116106 and US Patent No. 8,431,120 (from Bi-PA), Trichoderma atroviride, strain CNCM I-1237 (such as from Agrauxine WP) + Trichoderma viride (such as the product TrichoPlus from BASF), Trichoderma gamsii (formerly Trichoderma viride), Trichoderma gamsii (formerly Trichoderma viride) strain ICC 080 (IMI CC 392151CABI) (available from Agrobierso Mexico obtained) + TX + TX, Trichoderma gamsii strain ICC080 (IMICC 392151CABI + TX, such as BioDerma from Agrobierso Mexico + TX), + TX + TX, Trichoderma hamatum, Trichoderma hamatum, having the registration number ATCC 28012, Trichoderma harzianum, Trichoderma harzianum rifai T39 (such as from Makhteshim ) + TX, Trichoderma harzianum strain Cepa SimbT5 (from Simbiose Agro) + TX + TX, Trichoderma harzianum strain DB 103 (available from Dagutat Biolab as 7456) + TX, Trichoderma harzianum strain ITEM 908 (such as Trianum-P from Koppert) + TX, Trichoderma harzianum strain T-22 (such as Trianum-P from Andermatt Biocontrol or Koppert) + TX, Trichoderma harzianum strain TH35 (such as Root-Pro from Mycontrol) + TX, Trichoderma polysporum strain IMI 206039 (such as Binab TF WP from BINAB Bio-Innovation AB, Sweden) + TX, Trichodermastromaticum, with accession number Ts3550 (such as Tricovab from CEPLAC, Brazil) + TX, Trichoderma viride (also known as Gliocladium virens) especially strain GL-21 (such as SoilGard from Certis USA) + TX, Trichoderma viride strain G-41 + TX, formerly known as Gliocladium virens (accession number ATCC 20906) (such as PLUS WP and PLUS WP) + TX, Trichoderma viride especially strain B35 (Pietr et al. + TX, 1993 + TX, Zesz. Nauk. A R w Szczecinie 161:125-137) + TX, Trichoderma viride strain TV1 (such as Trianum-P from Koppert) + TX, Ulocladium oudemansii strain U3 + TX, with accession number NM 99 / 06216 (such as and from BioWorks) + TX, ) + TX, Verticillium albo-atrum (formerly Verticillium dahliae) strain WCS850 + TX, with accession number WCS850, deposited at the Central Bureau for Fungal Cultures (such as ) + TX, Verticillium chlamydosporium + TX;

[0322] including the following bacteria: a mixture of Azotobacter vinelandii and Clostridium pasteurianum (available from Agrinos as ) + TX, a mixture of Bacillus licheniformis FMCH001 and Bacillus subtilis FMCH002 (available from FMC as (WG) + TX, (WP)) + TX, Sesbania rostrata + TX, especially strain ZB - SK - 5 + TX, Azospirillum brasilense (e.g., + TX, from KALO + TX ) + TX, Azospirillum lipoferum (e.g., + TX, VERTEX - IF from TerraMax + TX TM ) + TX, Azotobacter chroococcum + TX, especially strain H23 + TX, Azotobacter vinelandii + TX, especially strain ATCC 12837 + TX, Bacillus amyloliquefaciens BS27 (Accession No. NRRL B - 5015) + TX, Bacillus amyloliquefaciens especially strain FZB42 (e.g., from ABiTEP GmbH + TX ) + TX, Bacillus amyloliquefaciens especially strain IN937a + TX, Bacillus amyloliquefaciens pm414 (from Biofilm Crop Protection ) + TX, Bacillus amyloliquefaciens SB3281 (ATCC#PTA - 7542 + TX, WO 2017 / 205258) + TX, Bacillus amyloliquefaciens TJ1000 (available from Novozymes as ) + TX, a member of the family Bacillaceae EE128 (NRRL No. B - 50917) + TX, a member of the family Bacillaceae EE349 (NRRL No. B - 50928) + TX, Bacillus cereus especially strain BP01 (ATCC 55675 + TX, e.g., from Arysta Lifescience + TX ) + TX, Bacillus mycoides BT155 (NRRL No. B - 50921) + TX, Bacillus mycoides BT46 - 3 (NRRL No. B - 50922) + TX, Bacillus mycoides EE118 (NRRL No. B - 50918) + TX, Bacillus mycoides EE141 (NRRL No. B - 50916) + TX, Bacillus pumilus especially strain GB34 (e.g., YIELD from Bayer CropScience GmbH + TX ) +TX, +TX, Bacillus pumilus, particularly strain QST2808 (Accession No. NRRL No. B - 30087) +TX, Bacillus siamensis, particularly strain KCTC 13613T +TX, Bacillus subtilis, particularly strain AQ30002 (Accession No. NRRL No. B - 50421 and described in U.S. Patent Application No. 13 / 330,576) +TX, Bacillus subtilis, particularly strain AQ30004 (NRRL No. B - 50455 and described in U.S. Patent Application No. 13 / 330,576) +TX, Bacillus subtilis, particularly strain MBI 600 (e.g., from BASF SE ) +TX, Bacillus subtilis rm303 (from Biofilm Crop Protection ) +TX, Bacillus subtilis strain BU1814 (available from BASF SE ) +TX, Bacillus tequilensis, particularly strain NII - 0943 +TX, Bacillus thuringiensis BT013A (NRRL No. B - 50924), also known as Bacillus thuringiensis 4Q7 +TX, Bradyrhizobium japonicum (e.g., from Novozymes ) +TX, Acidovorax delafieldii, particularly strain RAY209 (e.g., from Brett Young Seeds ) +TX, Lactobacillus species (e.g., from LactoPAFI ) +TX, Mesorhizobium (e.g., +TX, NODULATOR from BASF SE) +TX, Paenibacillus polymyxa, particularly strain AC - 1 (e.g., from Green Biotechnology Co., Ltd. ) +TX, Pseudomonas aeruginosa, particularly strain PN1 +TX, Pseudomonas proradix (e.g., from Sourcon Padena ) +TX, Rhizobium leguminosarium biovar viciae (e.g., +TX, NODULATOR from BASF SE) +TX, Rhizobium leguminosarium, particularly biovar viciae strain Z25 (Accession No. CECT 4585) +TX, Serratia marcescens, particularly strain SRM (Accession No. MTCC 8708) +TX+TX, Sinorhizobium meliloti strain NRG - 185 - 1 (from Bayer CropScience GOLD) +TX, Thiobacillus species (e.g., from Cropaid Ltd, UK ) +TX;

[0323] Myrothecium verrucaria strain AARC-0255 (e.g., DiTera from Valent Biosciences) TM ) + TX, Penicillium bilaii strain ATCC 22348 (e.g., ) + TX, Penicillium bilaii strain ATCC ATCC20851 + TX, Purpureocillium lilacinum (formerly Paecilomyces lilacinus) strain 251 (AGAL 89 / 030550 + TX, e.g., BioAct from Bayer CropScience) + TX, Pythium oligandrum strain DV74 + TX, Pythium oligandrum strain M1 (ATCC 38472, e.g., Polyversum + TX, CZ from Bioprepraty) + TX, Rhizopogon amylopogon (from Agri-Enterprise, LLC (formerly Helena Chemical Company's Myco-Sol) + TX, Rhizopogon fulvigleba (e.g., from Agri-Enterprise, LLC (formerly Helena Chemical Company's Myco-Sol) + TX, Talaromyces flavus strain V117b + TX, Trichoderma asperellum strain (Eco-T from Plant Health Products, ZA) + TX;

[0324] Mercuric oxide + TX, octhilinone + TX, thiophanate-methyl + TX;

[0325] MGK 264 + TX, 2-(2-butoxyethoxy)ethyl piperate + TX, 2-isovalerylindan-1,3-dione + TX, 4-(quinoxalin-2-ylamino)benzenesulfonamide + TX, 5-(1,3-benzodioxol-5-yl)-3-hexylcyclohex-2-enone + TX, acifluorfen + TX, acifluorfen-S-methyl + TX, alpha-bromadiolone + TX, alpha-chloroalcohol + TX, aluminium phosphide + TX, anthraquinone + TX,antu + TX, arsenic trioxide + TX, barium carbonate + TX, benoxacor + TX, biphenyl urea + TX, bromadiolone + TX, bromethalin + TX, bromfenacoum + TX, calcium cyanide + TX, chloralose + TX, chlorophacinone + TX, cholecalciferol + TX, cloquintocet (including cloquintocet-mexyl) + TX, copper naphthenate + TX, copper oxychloride + TX, chlorophacinone + TX, coumatetralyl + TX, coumatetralyl + TX, coumatetralyl + TX, cyprosulfamide + TX, diazinon + TX, dimethachlor + TX, dicyclopentadiene + TX, difenacoum + TX, thiafentanil + TX, diphacinone + TX, calciferol + TX, farnesol + TX, farnesol with nerolidol + TX, fenchlorazole (including fenchlorazole-ethyl) + TX, fenclorim + TX, flocoumafen + TX, fluoroacetamide + TX, flupropacil + TX, flupropacil hydrochloride + TX, flupoxam + TX, flurazole + TX, gamma-HCH + TX, guazatine + TX, guazatine acetate + TX, HCH + TX, hydrogen cyanide + TX, hymexazol + TX, methyl iodide + TX, isoxadifen (including isoxadifen-ethyl) + TX, lindane + TX, magnesium phosphide + TX, MB-599 + TX, mefenpyr (including mefenpyr-diethyl) + TX, mefenpyrdiethyl + TX, methiocarb + TX, methyl bromide + TX, nerolidol + TX, pindone + TX, petroleum oils + TX, phosdrin + TX, phosphine + TX, phosphorus + TX, pival + TX, piperonyl butoxide + TX, piperonyl butoxide + TX, potassium arsenite + TX, thiabendazole + TX, propyl isomer + TX, pyridin-4-amine + TX, pyrinuron + TX, polygonum cuspidatum extract + TX, ribavirin + TX, S421 + TX, scilliroside + TX, sesamex + TX, sesamin + TX, sodium arsenite + TX, sodium cyanide + TX, sodium fluoroacetate + TX, strychnine + TX, sulfoxide + TX, thallium sulfate + TX, selamectin + TX, methomyl + TX, warfarin + TX, zinc naphthenate + TX, zinc phosphide + TX, ziram + TX.

[0326] The reference in brackets after the active ingredient, if any, e.g. [3878-19-1], refers to the Chemical Abstracts Registry Number. The mixing compatibilities described above are known. Where the active ingredients are included in "The Pesticide Manual" ["The Pesticide Manual - A World Compendium"; 13th Edition; Editor: C.D.S.TomLin; The British Crop Protection Council], they are described therein by the entry numbers given in the round brackets above for the particular compounds; for example, the compound "abamectin" is described by the entry number (1). Where "[CCN]" is added above to a particular compound, the compound in question is included in "Compendium of Pesticide Common Names", which can be obtained on the Internet [A. Wood; Compendium of Pesticide Common Names , 1995 - 2004]; for example, the compound "acetoprole" is described at the Internet address http: / / www.alanwood.net / pesticides / acetoprole.html .

[0327] Most of the above active ingredients are referred to above by the so-called "common name", using the corresponding "ISO common name" or another "common name" in individual cases. If the name is not a "common name", the type of name used is replaced by the name given in the round brackets for the particular compound; in such cases, the IUPAC name, IUPAC / Chemical Abstracts name, "chemical name", "traditional name", "compound name" or "research code" is used, or if neither one of those names nor the "common name" is used, the "alias" is used. "CAS Registry Number" means the Chemical Abstracts Registry Number.

[0328] An active ingredient mixture of a compound of formula (I) selected from the compounds defined in Tables 1 to 7 and Table P” and the above-mentioned active ingredient comprises a compound selected from the compounds defined in Tables 1 to 7 and Table P and the above-mentioned active ingredient, and the compound and the active ingredient preferably have a mixing ratio of from 100:1 to 1:6000, especially from 50:1 to 1:50, more especially from 20:1 to 1:20, even more especially from 10:1 to 1:10, very especially from 5:1 and 1:5, particularly preferably from 2:1 to 1:2, and equally preferably from 4:1 to 2:1, especially 1:1, or 5:1, or 5:2, or 5:3, or 5:4, or 4:1, or 4:2, or 4:3, or 3:1, or 3:2, or 2:1, or 1:5, or 2:5, or 3:5, or 4:5, or 1:4, or 2:4, or 3:4, or 1:3, or 2:3, or 1:2, or 1:600, or 1:300, or 1:150, or 1:35, or 2:35, or 4:35, or 1:75, or 2:75, or 4:75, or 1:6000, or 1:3000, or 1:1500, or 1:350, or 2:350, or 4:350, or 1:750, or 2:750, or 4:750. Those mixing ratios are by weight.

[0329] The mixture as described above can be used in a method for controlling pests, which method comprises applying a composition comprising the mixture as described above to the pests or their environment, except for methods for treating the human or animal body by surgery or therapy and diagnostic methods practiced on the human or animal body.

[0330] A mixture of a compound of formula (I) comprising a compound selected from the compounds defined in Tables 1 to 7 and Table P and one or more of the above-mentioned active ingredients can be applied, for example, in a single “ready-to-use” form, in a combined spray mixture (which consists of separate formulations of the individual active ingredient components, such as “tank mixes”), and by using these individual active ingredients in combination when applied in a sequential manner (i.e., one after another in a moderately short time period, such as a few hours or days). The order of applying the compound of formula (I) and the above-mentioned active ingredients is not crucial for carrying out the present invention.

[0331] The composition according to the invention may further comprise additional solid or liquid auxiliaries, such as stabilizers, for example unepoxidized or epoxidized vegetable oils (such as epoxidized coconut oil, rapeseed oil or soybean oil), defoamers (such as silicone oils), preservatives, viscosity regulators, binders and / or tackifiers, fertilizers or other active ingredients for obtaining specific effects, such as bactericides, fungicides, nematicides, plant activators, molluscicides or herbicides.

[0332] The compositions according to the invention are prepared in a manner known per se, in the absence of auxiliaries, for example by grinding, sieving and / or compressing the solid active ingredient; and in the presence of at least one auxiliary, for example by intimately mixing the active ingredient with one or more auxiliaries and / or grinding the active ingredient together with one or more auxiliaries. These processes for preparing the compositions and the use of compound I for preparing these compositions are also the subject of the invention.

[0333] The methods of applying these compositions, i.e. the methods of controlling pests of the abovementioned type, such as spraying, atomizing, dusting, brushing, coating, broadcasting or watering - which are selected to be suitable for the intended purpose in the general case - and the use of these compositions for controlling pests of the abovementioned type are further subjects of the invention. Typical concentration ratios are of the active ingredient between 0.1 and 1000 ppm, preferably between 0.1 and 500 ppm. The application rate per hectare is generally from 1 g to 2000 g of active ingredient per hectare, in particular from 10 g / ha to 1000 g / ha, preferably from 10 g / ha to 600 g / ha.

[0334] In the field of crop protection, the preferred method of application is application to the leaves of these plants (foliar application), it being possible to select the frequency and rate of application to correspond to the infestation risk of the pest in question. Alternatively, the active ingredient can reach the plant via the root system (systemic action), which is achieved by soaking the site of these plants with a liquid composition or by introducing the active ingredient in solid form into the site of the plant (for example into the soil, for example in the form of granules (soil application)). In the case of rice crops, such granules can be metered into the flooded paddy field.

[0335] The compounds of formula (I) according to the invention and their compositions are also suitable for protecting plant propagation material (such as seeds, if fruits, tubers or grains, or nursery plants) against pests of the abovementioned type. The propagation material can be treated with the compound before planting, for example the seeds can be treated before sowing. Alternatively, the compound can be applied to the seed grains (coating), which is achieved by dipping the grains into a liquid composition or by applying a layer of solid composition. It is also possible to apply these compositions when the propagation material is planted in the application site, for example by applying these compositions into the seed furrow during drilling. These methods for treating plant propagation material and the plant propagation material so treated are additional subjects of the invention. Typical treatment rates will depend on the plant to be controlled and the pest / fungus, and are generally between 1 and 200 g per 100 kg of seeds, preferably between 5 and 150 g per 100 kg of seeds, such as between 10 and 100 g per 100 kg of seeds.

[0336] The term "seed" includes all kinds of seeds and plant propagules, including but not limited to true seeds, seed pieces, suckers, grains, bulbils, fruits, tubers, cereals, rhizomes, cuttings, cut shoots and the like and in the preferred embodiment means true seeds.

[0337] The invention also includes seeds coated or treated with a compound of formula I or seeds containing a compound of formula I. Although more or less of the ingredient may penetrate into the seed material depending on the method of application, the terms "coated or treated with and / or containing" generally mean that, at the time of application, in most cases, the active ingredient is on the surface of the seed. When the seed product is (re)planted, it can absorb the active ingredient. In an embodiment, the invention makes it possible to obtain plant propagation material to which a compound of formula I adheres. In addition, a composition containing plant propagation material treated with a compound of formula I is thereby made available.

[0338] Seed treatment includes all suitable seed treatment techniques known in the art, such as seed dressing, seed coating, seed dusting, seed soaking and seed granulation. The seed treatment application of the compound of formula (I) can be carried out by any known method, such as spraying or dusting the seeds before sowing or during sowing / planting.

[0339] The compounds of the invention can be distinguished from other similar compounds by virtue of greater efficacy at low application rates and / or different pest control, which can be demonstrated by those skilled in the art using experimental procedures, using lower concentrations (if required), for example 10 ppm, 5 ppm, 2 ppm, 1 ppm or 0.2 ppm; or lower application rates, such as per m 2 300, 200 or 100 mg AI. Greater efficacy can be observed through increased safety (towards non-target organisms above and below ground, such as fish, birds and bees), improved physico-chemical properties or increased biodegradability.

[0340] In each aspect and embodiment of the invention, "consisting essentially of" and its variations are preferred embodiments of "comprising" and its variations, and "consisting of" and its variations are preferred embodiments of "consisting essentially of" and its variations.

[0341] The disclosure of this application makes it possible to obtain each combination of the embodiments disclosed herein.

[0342] Biological examples:

[0343] The following examples are used to illustrate the present invention. Some compounds of the present invention may differ from known compounds in greater efficacy at low application rates, which can be demonstrated by those skilled in the art using the experimental procedures outlined in the examples, using lower application rates (if necessary), for example, 50 ppm, 24 ppm, 12.5 ppm, 3 ppm, 0.8 ppm or 0.2 ppm.

[0344] Example B1: Tetranychus urticae (Two-spotted spider mite): Feeding / contact activity

[0345] Soybean leaf discs on agar in 24-well microtiter plates were sprayed with an aqueous test solution prepared from a 10,000 ppm DMSO stock solution. After drying, the leaf discs were infested with a mite population of mixed ages. Eight days after infestation, these samples were evaluated for mortality of the mixed population (active stage).

[0346] The following compounds produced at least 80% mortality at an application rate of 12.5 ppm or even lower:

[0347] P.1, P.2, P.3, P.4, P.5, P.6, P.7.

[0348] Comparison:

[0349] Compound A is dimethylsulfonamide known from Nippon Soda WO 2019039429. Compound B is a methylsulfonamide analogue of compound A.

[0350] Compound P.4 is an ethyl(methyl)sulfonamide analogue of compound A. Compound P.4 is an ethylsulfonamide analogue of compound A. In the assay as described above in Example B1, the ethyl-containing sulfonamides P.4 and P.6 showed better acaricidal activity than compounds A and B.

[0351]

Claims

1. A compound having the formula (I) wherein R 1 is CN or C(=S)NH2; R 2 is H or methyl; R 3 is a C1-C2-alkyl, C1-C2-haloalkyl, C3-C6-cycloalkyl, C1-C2-alkoxy-C1-C2-alkyl; R 4 independently selected from halogen, C1-C2-haloalkyl, C1-C2-haloalkoxy, -O-C 1-2 haloalkanediyl-O-; q is 1, 2 or 3; or or an agronomically acceptable salt, enantiomer, tautomer and / or N-oxide of the compound having formula I.

2. The compound according to claim 1, wherein R 1 is a cyano group.

3. The compound according to claim 1 or claim 2, wherein R 3 is a C1-C2-alkyl, C1-C2-haloalkyl, C3-C4-cycloalkyl, or C1-C2-alkoxy-C1-C2-alkyl.

4. The compound according to any one of claims 1 to 3, wherein, R 4 independently selected from one or two substituents from halogen, C1-C2-haloalkyl, and C1-C2-haloalkoxy, or -OCF2O- (i.e., q is 1 or 2).

5. The compound according to any one of claims 1 to 4, wherein R 4 Independently selected from one or two substituents from fluorine, chlorine, bromine, trifluoromethyl, difluoromethyl, difluoromethoxy, and trifluoromethoxy, or -OCF2O- (i.e., q is 1 or 2).

6. The compound having formula I according to claim 1, selected from the group consisting of: 1-[5-Cyano-6-(2,2-difluoro-1,3-benzodioxol-5-yl)-2-(methoxymethyl)pyridine-3-carbonyl]-N-ethyl-N-methyl-piperidine-4-sulfonamide (Compound P.1); 1-[5-Cyano-6-(2,2-difluoro-1,3-benzodioxol-5-yl)-2-methyl-pyridine-3-carbonyl]-N-ethyl-N-methyl-piperidine-4-sulfonamide (Compound P.2); 1-[5-Cyano-6-(2,2-difluoro-1,3-benzodioxol-5-yl)-2-(difluoromethyl)pyridine-3-carbonyl]-N-ethyl-N-methyl-piperidine-4-sulfonamide (Compound P.3); 1-[5-Cyano-2-(trifluoromethyl)-6-[4-(trifluoromethyl)phenyl]pyridine-3-carbonyl]-N-ethyl-N-methyl-piperidine-4-sulfonamide (Compound P.4); 1-[5-Cyano-6-(2,2-difluoro-1,3-benzodioxol-5-yl)-2-(difluoromethyl)pyridine-3-carbonyl]-N-ethyl-piperidine-4-sulfonamide (Compound P.5); 1-[5-Cyano-2-(trifluoromethyl)-6-[4-(trifluoromethyl)phenyl]pyridine-3-carbonyl]-N-ethyl-piperidine-4-sulfonamide (Compound P.6); and 1-[5-Cyano-6-(2,2-difluoro-1,3-benzodioxol-5-yl)-2-(methoxymethyl)pyridine-3-carbonyl]-N-ethyl-piperidine-4-sulfonamide (Compound P.7).

7. A composition comprising the compound having formula I according to any one of claims 1 to 6, one or more auxiliaries and diluents, and optionally one or more other active ingredients.

8. A method for combating and controlling insects, mites, nematodes or molluscs, the method comprising applying an insecticidally, acaricidally, nematicidally or molluscicidally effective amount of the compound having formula I according to any one of claims 1 to 6 or the composition according to claim 7 to the pest, to the locus of the pest, or to a plant susceptible to attack by the pest.

9. A method for protecting plant propagation material against attack by insects, mites, nematodes or molluscs, the method comprising treating the propagation material or the site on which the propagation material is planted with an effective amount of the compound having formula I according to any one of claims 1 to 6 or the composition according to claim 7.

10. A plant propagation material, such as a seed, comprising the compound having formula I according to any one of claims 1 to 6 or the composition according to claim 7, or treated with the compound or the composition, or having the compound or the composition attached thereto.

11. A process for preparing a compound of formula I according to any one of claims 1 to 6, the process being carried out by: reacting an acid of formula II, wherein R 1 , R 3 , R 4 and q are as defined for formula I, with an amine of formula III, wherein R 2 is hydrogen or methyl, or with a salt thereof.

Images