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WO2023037249A1 - Composés carboxamide aromatiques contenant des sulfoximines/sulfilimine et leur utilisation - Google Patents

Composés carboxamide aromatiques contenant des sulfoximines/sulfilimine et leur utilisation Download PDF

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Publication number
WO2023037249A1
WO2023037249A1 PCT/IB2022/058389 IB2022058389W WO2023037249A1 WO 2023037249 A1 WO2023037249 A1 WO 2023037249A1 IB 2022058389 W IB2022058389 W IB 2022058389W WO 2023037249 A1 WO2023037249 A1 WO 2023037249A1
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alkyl
ring
group
ethyl
formula
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Inventor
Ajay Singh Yadav
Rohit Saxena
Jagadish Pabba
Bharat Uttamrao SHINDE
Ganesh Raosaheb DHAGE
Aditya PATWA
Prashant Bhanudas HEGADE
Ravikumar Suryanarayana SARAGUR
Alexander G.M. KLAUSENER
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PI Industries Ltd
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PI Industries Ltd
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/60—1,4-Diazines; Hydrogenated 1,4-diazines
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
    • A01N43/647—Triazoles; Hydrogenated triazoles
    • A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
    • A01P7/00—Arthropodicides
    • A01P7/04—Insecticides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings

Definitions

  • the present invention relates to compounds of formula (I). More particularly, the present invention relates to sulfoximines/sulfilimine containing aromatic carboxamide compounds of formula (I) and a process for the preparation thereof. The present invention further relates to compositions comprising those compounds, and to their use as pest control agents.
  • BACKGROUND OF THE INVENTION Invertebrate pests, in particular arthropods and nematodes, destroy growing and harvested crops causing severe economic loss to the food supply.
  • insects attack on wooden dwellings and commercial structures, thereby causing large economic losses to property. Therefore, there is an ongoing need for new agents for combating invertebrate pests such as insects, arachnids and nematodes.
  • the currently available modern insecticides and acaricides have to satisfy many requirements, for example regarding the level of activity, long lasting efficacy, broadness of insecticidal spectrum and other beneficial effects, and the possible use thereof.
  • Efforts have been made during the past decades to develop selective insecticides that are acting specifically on biochemical modes of action being present only in insects or mites, but additionally showing properties that differ from known insecticides in an advantageous way.
  • heteroaryl-azole compounds for the use in controlling ectoparasites on animals and for the control of animal pests including arthropods and insects in the field of plant protection are disclosed in prior art for example: WO2021099303, WO 2020002563, WO 2020053364, WO 2020053365, WO 2020079198, WO 2020094363, WO 2019197468, WO 2019201835, WO 2019202077 and WO 2019206799.
  • WO2021099303 WO 2020002563, WO 2020053364, WO 2020053365, WO 2020079198, WO 2020094363, WO 2019197468, WO 2019201835, WO 2019202077 and WO 2019206799.
  • the sulfilimines or sulfoximines containing aromatic carboxamide compounds have advantages over the prior art, for example, by showing improved insecticidal activity.
  • the present invention envisages such compounds that satisfy or overcome drawbacks associated with the prior art. It has now surprisingly been found that certain novel, pesticidally active sulfoximines/sulfilimine containing aromatic carboxamide compounds being subject of this invention, have favorable properties as pesticides and are environmentally safer, as desired.
  • the present invention provides sulfoximines/sulfilimine containing aromatic carboxamide compounds of formula (I) or agriculturally acceptable salts, stereo-isomers, diastereomers, enantiomers, tautomers, metal complexes, polymorphs, or N-oxides thereof, Formula (I) wherein, ring-A, ring-B, ring-C, R 2 , R 3a , and R 3b are as defined in the detailed description.
  • the present invention provides a process for preparing compounds of formula (I) or agriculturally acceptable salts thereof.
  • the present invention provides a composition for controlling or preventing invertebrate pests comprising a biologically effective amount of the compound of formula (I), agriculturally acceptable salts, stereo-isomers, diastereomers, enantiomers, tautomers, metal complexes, polymorphs, or N-oxides thereof and at least one additional component selected from the group consisting of surfactants and auxiliaries.
  • the composition further comprises at least one additional biologically active and compatible compound selected from fungicides, insecticides, nematicides, acaricides, biopesticides, herbicides, plant growth regulators, antibiotics, fertilizers or nutrients.
  • the present invention provides the use of the compound of formula (I), agriculturally acceptable salts, stereo-isomers, diastereomers, enantiomers, tautomers, metal complexes, polymorphs, or N-oxides, composition or combination thereof, for combating invertebrate pests in agricultural crops and/or horticultural crops or parasites on animals.
  • the present invention provides a method of combating invertebrate pests comprising contacting the invertebrate pests, their habitat, breeding ground, food supply, plant, seed, soil, area, material or environment in which the invertebrate pests are growing or may grow, or the materials, plants, seeds, soils, surfaces or spaces to be protected from pest attack or infestation with a biologically effective amount of the compound of formula (I) or agriculturally acceptable salts, stereo-isomers, diastereomers, enantiomers, tautomers, metal complexes, polymorphs, or N-oxides thereof as well as compositions or combinations thereof.
  • transitional phrase “consisting of” excludes any element, step or ingredient not specified. If in the claim, such would close the claim to the inclusion of materials other than those recited except for impurities ordinarily associated therewith. When the phrase “consisting of” appears in a clause of the body of a claim, rather than immediately following the preamble, it limits only the element set forth in that clause; other elements are not excluded from the claim as a whole.
  • the transitional phrase “consisting essentially of” is used to define a composition or method that includes materials, steps, features, components or elements, in addition to those literally disclosed, provided that these additional materials, steps, features, components or elements do not materially affect the basic and novel characteristic(s) of the claimed invention.
  • the term "invertebrate pest” includes arthropods, gastropods and nematodes of economic importance as pests.
  • arthropod includes insects, mites, spiders, scorpions, centipedes, millipedes, pill bugs and symphylans.
  • gastropod includes snails, slugs and other Stylommatophora.
  • nematode refers to a living organism of the Phylum Nematoda.
  • helminths includes roundworms, heartworms, phytophagous nematodes (Nematoda), flukes (Tematoda), acanthocephala and tapeworms (Cestoda).
  • agronomic refers to the production of field crops such as for food, feed and fiber and includes the growth of corn, soybeans and other legumes, rice, cereals (e.g., wheat, oats, barley, rye, rice, maize), leafy vegetables (e.g., lettuce, cabbage, and other cole crops), fruiting vegetables (e.g., tomatoes, pepper, eggplant, crucifers and cucurbits), potatoes, sweet potatoes, grapes, cotton, tree fruits (e.g., pome, stone and citrus), small fruits (berries, cherries) and other specialty crops (e.g., canola, sunflower, olives).
  • nonagronomic refers to other than field crops, such as horticultural crops (e.g., greenhouse, nursery or ornamental plants not grown in a field), residential, agricultural, commercial and industrial structures, turf (e.g., sod farm, pasture, golf course, lawn, sports field, etc.), wood products, stored product, agro-forestry and vegetation management, public health (i.e. human) and animal health (e.g., domesticated animals such as pets, livestock and poultry, undomesticated animals such as wildlife) applications.
  • Nonagronomic applications include protecting an animal from an invertebrate parasitic pest by administering a parasiticidally effective (i.e.
  • the terms "parasiticidal” and “parasiticidally” refers to observable effects on an invertebrate parasite pest to provide protection of an animal from the pest. Parasiticidal effects typically relate to diminishing the occurrence or activity of the target invertebrate parasitic pest. Such effects on the pest include death, retarded growth, diminished mobility or lessened ability to remain on or in the host animal, reduced feeding and inhibition of reproduction. These effects on invertebrate parasite pests provide control (including prevention, reduction or elimination) of parasitic infestation or infection of the animal.
  • the compounds of the present disclosure may be present either in pure form or as mixtures of different possible isomeric forms such as stereoisomers or constitutional isomers.
  • the various stereoisomers include enantiomers, diastereomers, chiral isomers, atropisomers, conformers, rotamers, tautomers, optical isomers, polymorphs, and geometric isomers. Any desired mixtures of these isomers fall within the scope of the claims of the present disclosure.
  • one stereoisomer may be more active and/or may exhibit beneficial effects when enriched relative to the other isomer(s) or when separated from the other isomer(s).
  • enantiomerically enriched refers to a chiral substance whose enentiomeric ratio is greater than 50:50 but less than 100:0.
  • aliphatic compound/s or “aliphatic group/s” used herein is an organic compound/s whose carbon atoms are linked in straight chains, branched chains, or non-aromatic rings.
  • alkyl used either alone or in compound words such as “alkylthio” or “haloalkyl” or -N(alkyl) or alkylcarbonylalkyl or alkylsuphonylamino includes straight-chain or branched C 1 to C 12 alkyl, preferably C 1 to C 8 alkyl, more preferably C 1 to C 6 alkyl.
  • alkyl include methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, pentyl, 1-methylbutyl, 2- methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, hexyl, 1,1-dimethylpropyl, 1,2- dimethylpropyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2- dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethyl-1-methylpropyl and l
  • the alkyl is at the end of a composite substituent, as, for example, in alkylcycloalkyl
  • the part of the composite substituent at the start for example the cycloalkyl
  • other radicals for example alkenyl, alkynyl, hydroxyl, halogen, carbonyl, carbonyloxy and the like, are at the end.
  • cyanoalkyl refers to straight-chain or branched alkyl groups having 1 to 6 (“C 1 - C 6 -cyanoalkyl”) or 1 to 4 (“C 1 -C4-cyanoalkyl”) carbon atoms (as mentioned above), where 1 or 2, preferably 1 , of the hydrogen atoms in these groups are replaced by a cyano (CN) group.
  • CN cyano
  • Non limiting examples are cyanomethyl, 1-cyanoethyl, 2-cyanoethyl, 1 -cyanopropyl, 2- cyanopropyl, 3-cyanopropyl, 1-cyanobutyl, 2-cyanobutyl, 3-cyanobutyl, 4-cyanobutyl and the like.
  • alkenyl used either alone or in compound words includes straight-chain or branched C2 to C 12 alkenes, preferably C2 to C 8 alkenes, more preferably C2 to C 6 alkenes.
  • Representative examples of alkenes include ethenyl, 1-propenyl, 2-propenyl, 1-methylethenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1- propenyl, 2-methyl-1-propenyl, l-methyl-2 -propenyl, 2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3- pentenyl, 4-pentenyl, 1-methyl-1-butenyl, 2-methyl-1-butenyl, 3-methyl-1-butenyl, l-methyl-2-butenyl, 2- methyl-2-butenyl, 3-methyl-2-butenyl, l-methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl-3-but
  • Alkenyl also includes polyenes such as 1,2-propadienyl and 2,4-hexadienyl. This definition also applies to alkenyl as a part of a composite substituent, for example haloalkenyl and the like, unless defined specifically elsewhere.
  • alkynyl used either alone or in compound words includes straight-chain or branched C2 to C 12 alkynes, preferably C2 to C 8 alkynes, more preferably C2 to C 6 alkynes.
  • Non-limiting examples of alkynes include ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl, 1- pentynyl, 2-pentyny1,3-pentynyl, 4-pentynyl, l-methyl-2-butynyl, l-methyl-3-butynyl, 2-methyl-3-butynyl, 3-methyl-1-butynyl, 1,1-dimethyl-2-propynyl, 1-ethyl -2-propynyl, 1-hexynyl, 2-hexynyl, 3-hexynyl, 4- hexynyl, 5-hexynyl, 1-methyl-2-pentynyl, l-methyl-3-pentynyl, 1-methyl-4-pentynyl, 2-methyl-3- pentynyl, 2-
  • alkynyl as a part of a composite substituent, for example haloalkynyl etc., unless specifically defined elsewhere.
  • alkynyl can also include moieties comprised of multiple triple bonds such as 2,5-hexadiynyl.
  • cycloalkyl means alkyl closed to form a ring. Non-limiting examples include but are not limited to cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl. This definition also applies to cycloalkyl as a part of a composite substituent, for example cycloalkylalkyl etc., unless specifically defined elsewhere.
  • cycloalkenyl means alkenyl closed to form a ring including monocyclic, partially unsaturated hydrocarbyl groups. Non-limiting examples include but are not limited to cyclopropenyl, cyclopentenyl and cyclohexenyl. This definition also applies to cycloalkenyl as a part of a composite substituent, for example cycloalkenylalkyl etc., unless specifically defined elsewhere.
  • cycloalkynyl means alkynyl closed to form a ring including monocyclic, partially unsaturated groups. Non-limiting examples include but are not limited to cyclopropynyl, cyclopentynyl and cyclohexynyl.
  • cyanocycloalkyl refers to alkyl closed to form a ring, groups having 3 to 8 (“C 3 - C 8 -cyanoalkyl”) carbon atoms (as mentioned above), where 1 or 2, preferably 1, of the hydrogen atoms in these groups are replaced by a cyano (CN) group.
  • Non limiting examples are 1-cyanocyclopropyl, 2- cyanocyclopropyl, 1 -cyanocyclobutyl, 2-cyanocyclobutyl, 3-cyanocyclobutyl, 1-cyanocyclopentyl, 2- cyanocyclopentyl, 3-cyclopentyl, 4-cyclopentyl, 1-cyanohexyl, 2-cyanohexyl, 3-cyanocyclohexyl, 4- cyanocyclohexyl and the like.
  • alkoxy used either alone or in compound words includes C 1 to C 12 alkoxy, preferably C 1 to C 8 alkoxy, more preferably C 1 to C 6 alkoxy.
  • alkoxy examples include methoxy, ethoxy, propoxy, 1- methylethoxy, butoxy, 1-methylpropoxy, 2-methylpropoxy, 1,1-dimethylethoxy, pentoxy, 1-methylbutoxy, 2-methylbutoxy, 3-methylbutoxy, 2,2-dimethylpropoxy, 1-ethylpropoxy, hexoxy, 1,1-dimethylpropoxy, 1,2-dimethylpropoxy, 1-methylpentoxy, 2-methylpentoxy, 3-methylpentoxy, 4-methylpentoxy, 1,1- dimethylbutoxy, 1,2-dimethylbutoxy, 1,3-dimethylbutoxy, 2,2-dimethylbutoxy, 2,3-dimethylbutoxy, 3,3- dimethylbutoxy, 1-ethylbutoxy, 2-ethylbutoxy, 1,1,2-trimethylpropoxy, 1,2,2-trimethylpropoxy, 1-ethyl-1- methylpropoxy and l-ethyl-2-methylpropoxy and the different isomers.
  • halogen either alone or in compound words such as “haloalkyl”, includes fluorine, chlorine, bromine or iodine. Further, when used in compound words such as “haloalkyl”, said alkyl may be partially or fully substituted with halogen atoms which may be the same or different.
  • haloalkyl include chloromethyl, bromomethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1- chloroethyl, 1-bromoethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2- fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl, pentafluoroethyl, 1,1-dichloro-2,2,2-trifluoroethyl, and 1,1,1-trifluoroprop-2-yl.
  • haloalkyl as a part of a composite substituent, for example haloalkylaminoalkyl etc., unless specifically defined elsewhere.
  • haloalkenyl haloalkynyl
  • alkenyl and alkynyl groups are present as a part of the substituent.
  • the term "hydroxy" means –OH
  • Amino means —NRR, wherein R can be H or any possible substituent such as alkyl.
  • Carbonyl means -C(O)-, carbonyloxy means -OC(O)-, sulfinyl means SO, sulfonyl means S(O) 2 .
  • carrier or “carbocyclic” or “carbocyclyl” include “aromatic carbocyclic ring systems” and “nonaromatic carbocylic ring systems” or polycyclic or bicyclic (spiro, fused, bridged, nonfused) ring compounds in which the ring may be aromatic or non-aromatic (where aromatic indicates that the Huckel rule is satisfied and non-aromatic indicates that the Huckel rule is not satisfied).
  • Non limiting examples of non-aromatic carbocyclic ring system are cyclopropyl, cyclobutyl, cyclopentyl, norbornyl and the like.
  • Non limiting examples of aromatic carbocyclic ring system are phenyl, naphthyl and the like.
  • aryl as used herein is a group that contains any carbon-based aromatic group including, but not limited to phenyl, naphthalene, biphenyl, anthracene, and the like.
  • the aryl group can be substituted or unsubstituted.
  • the aryl group can be a single ring structure or comprise multiple ring structures that are either fused ring structures or attached via one or more bridging groups such as a carbon-carbon bond.
  • aryl also comprising “aralkyl” refers to aryl hydrocarbon radicals including an alkyl portion as defined above.
  • Examples include benzyl, phenylethyl, and 6-napthylhexyl.
  • aralkenyl refers to aryl hydrocarbon radicals including an alkenyl portion, as defined above, and an aryl portion, as defined above. Examples include styryl, 3-(benzyl) prop-2-enyl, and 6-napthylhex-2-enyl.
  • hetero in connection with rings refers to a ring in which at least one ring atom is not carbon and which can contain 1 to 4 heteroatoms independently selected from the group consisting of nitrogen, oxygen and sulfur, provided that each ring contains no more than 4 nitrogens, no more than 2 oxygens and no more than 2 sulfurs.
  • heterocycle indicates that the Huckel rule is satisfied and the term “non-aromatic” indicates that the Huckel rule is not satisfied.
  • non-aromatic heterocycle or “non-aromatic heterocyclic” means three- to fifteen-membered, preferably three- to twelve-membered, saturated or partially unsaturated heterocycles containing one to four heteroatoms from the group of oxygen, nitrogen and sulphur: mono, bi- or tricyclic heterocycles which contain, in addition to the carbon ring members, one to three nitrogen atoms and/or one oxygen or sulphur atom or one or two oxygen and/or sulphur atoms; if the ring contains more than one oxygen atom, they are not directly adjacent; for example (but not limited to) oxiranyl, oxetanyl, aziridinyl, azetidinyl, thietanyl, thietanyl 1-oxide, thietanyl 1,1-dioxide, 2-tetrahydrofuranyl, 3-tetrahydrofuranyl, 2-tetrahydrothienyl, 3- te
  • heterocyclyl as a part of a composite substituent, for example heterocyclylalkyl etc., unless specifically defined elsewhere.
  • heteroaryl or "aromatic heterocyclic” means a 5 or 6-membered, fully unsaturated monocyclic ring system containing one to four heteroatoms from the group of oxygen, nitrogen and sulphur; if the ring contains more than one oxygen atom, they are not directly adjacent; 5-membered heteroaryl ring systems containing one to four nitrogen atoms or one to three nitrogen atoms and one sulphur or oxygen atom: 5- membered heteroaryl groups which, in addition to carbon atoms, may contain one to four nitrogen atoms or one to three nitrogen atoms and one sulphur or oxygen atom as ring members, for example (but not limited thereto) furyl, thienyl, pyrrolyl, isoxazolyl, isothiazolyl, pyrazolyl, oxazolyl,
  • 6-membered heteroaryl which contains one to four nitrogen atoms: 6-membered heteroaryl groups which, in addition to carbon atoms, may contain, respectively, one to three and one to four nitrogen atoms as ring members, for example (but not limited thereto) 2-pyridinyl, 3-pyridinyl, 4-pyridinyl, 3-pyridazinyl, 4- pyridazinyl, 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl, 2-pyrazinyl, 1,3,5-triazin-2-yl, 1,2,4-triazin-3-yl and 1,2,4,5-tetrazin-3-yl; benzofused 5-membered heteroaryl containing one to three nitrogen atoms or one nitrogen atom and one oxygen or sulphur atom: for example (but not limited to) indol-1-yl, indol-2-yl, indol- 3-yl, indol-4-yl, indol
  • Trialkylsilyl includes three branched and/or straight-chain alkyl radicals attached to and linked through a silicon atom such as trimethylsilyl, triethylsilyl and t-butyl-dimethylsilyl.
  • Hydrophilickylsilyl denotes at least one of the three alkyl radicals is partially or fully substituted with halogen atoms which may be the same or different.
  • alkoxytrialkylsilyl denotes at least one of the three alkyl radicals is substituted with one or more alkoxy radicals which may be the same or different.
  • trialkylsilyloxy denotes a trialkylsilyl moiety attached through oxygen.
  • the total number of carbon atoms in a substituent group is indicated by the “C i -C j " prefix where i and j are numbers from 1 to 21.
  • C 1 -C 3 alkylsulfonyl designates methylsulfonyl through propylsulfonyl
  • C 2 alkoxyalkyl designates CH 3 OCH 2
  • C 3 alkoxyalkyl designates, for example, CH 3 CH(OCH 3 ), CH 3 OCH 2 CH 2 or CH 3 CH 2 OCH 2
  • C4 alkoxyalkyl designates the various isomers of an alkyl group substituted with an alkoxy group containing a total of four carbon atoms, examples including CH 3 CH 2 CH 2 OCH 2 and CH 3 CH 2 OCH 2 CH 2 .
  • inventive compound of the present invention may, if appropriate, be present as mixtures of different possible isomeric forms, especially of stereoisomers, for example E and Z, threo and erythro, and also optical isomers, but if appropriate also of tautomers. Both the E and the Z isomers, and also the threo and erythro isomers, and the optical isomers, any desired mixtures of these isomers and the possible tautomeric forms are disclosed and claimed.
  • pest for the purpose of the present disclosure includes but is not limited to fungi, stramenopiles (oomycetes), bacteria, nematodes, mites, ticks, insects and rodents. Also pest is an animal or plant detrimental to humans or human concerns including crops, livestock and forestry.
  • plant is understood here to mean all plants and plant populations, such as desired and undesired wild plants or crop plants (including naturally occurring crop plants). Crop plants may be plants which can be obtained by conventional breeding and optimization methods or by biotechnological and genetic engineering methods or combinations of these methods, including the transgenic plants and including the plant cultivars which are protectable and non-protectable by plant breeders′ rights.
  • plant includes a living organism of the kind exemplified by trees, shrubs, herbs, grasses, ferns, and mosses, typically growing in a site, absorbing water and required substances through its roots, and synthesizing nutrients in its leaves by photosynthesis.
  • plant for the purpose of the present invention include but are not limited to agricultural crops such as wheat, rye, barley, triticale, oats or rice; beet, e.g. sugar beet or fodder beet; fruits and fruit trees, such as pomes, stone fruits or soft fruits, e.g.
  • leguminous plants such as lentils, peas, alfalfa or soybeans; oil plants, such as rape, mustard, olives, sunflowers, coconut, cocoa beans, castor oil plants, oil palms, ground nuts or soybeans; cucurbits, such as squashes, cucumber or melons; fiber plants, such as cotton, flax, hemp or jute; citrus fruit and citrus trees, such as oranges, lemons, grapefruits or mandarins; any horticultural plants, vegetables, such as spinach, lettuce, asparagus, cabbages, carrots, onions, tomatoes, potatoes, cucurbits or paprika; lauraceous plants, such as avocados, cinnamon or camphor; cucurbitaceae; oleaginous plants; energy and raw material plants, such as cereals, corn, soybean, other leguminous plants, rape, sugar cane or oil palm; tobacco; nuts; coffee; tea;
  • the plant for the purpose of the present invention include but is not limited to cereals, corn, rice, soybean and other leguminous plants, fruits and fruit trees, grapes, nuts and nut trees, citrus and citrus trees, any horticultural plants, cucurbitaceae, oleaginous plants, tobacco, coffee, tea, cacao, sugar beet, sugar cane, cotton, potato, tomato, onions, peppers and vegetables, ornamentals, any floricultural plants and other plants of use for humans and animals.
  • plant parts is understood to mean all parts and organs of plants above and below the ground.
  • plant parts includes but is not limited to cuttings, leaves, twigs, tubers, flowers, seeds, branches, roots including taproots, lateral roots, root hairs, root apex, root cap, rhizomes, slips, shoots, fruits, fruit bodies, bark, stem, buds, auxillary buds, meristems, nodes and internodes.
  • locus thereof includes soil, surroundings of plant or plant parts and equipment or tools used before, during or after sowing/planting a plant or a plant part.
  • the application of the compounds of the present disclosure or the compound of the present disclosure in a composition, optionally comprising other compatible compounds, to a plant or a plant material or locus thereof include application by a technique known to a person skilled in the art which includes but is not limited to spraying, coating, dipping, fumigating, impregnating, injecting and dusting.
  • the term "applied” means adhered to a plant or plant part either physically or chemically including impregnation.
  • the present invention provides sulfoximines/sulfilimine containing aromatic carboxamide compounds of formula (I), wherein, ring-A represents phenyl or 5-6-membered hetero-aromatic ring; wherein the ring-A may be optionally substituted with one R 1 ′ and/or one or more R 1 ;
  • R 1 is selected from the group consisting of hydrogen, halogen, cyano, nitro, SF 5, C 1 -C 6 -alkyl, C 2 -C 6 - alkenyl, C 2 -C 6 -alkynyl, C 1 -C 6 -haloalkyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -haloalkynyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 - halocycloalkyl, C 3 -C 8 -cycloalkyl-C 1 -C 6 -alkyl,
  • the present invention provides compounds of formula (I) contain a stereogenic center which is indicated with an asterisk in the structure below: Formula (I) wherein, R 3a is hydrogen, ring-A, ring-B, ring-C, R 2 and R 3b are as defined in the detailed description.
  • the present invention provides compounds of formula (IA), Formula (IA) wherein, ring-A, ring-B, ring-C, R 2, R 3a , R 3b , D′, R 8a and R 8b are as defined in the detailed description.
  • the present invention provides compounds of formula (IB), Formula (IB) wherein, ring-A, ring-B, ring-C, R 2, R 3a , R 3b , D, R 7a and R 7b are as defined in the detailed description.
  • the present invention provides compounds of formula (I), wherein ring-A is disubstituted with R 1 .
  • the present invention provides compounds of formula (I), wherein OR 4 is preferably selected from methoxy, ethoxy, propoxy, trifluoromethoxy, trifluoroethoxy, difluoromethoxy or cyclopropyloxy, cyclopropylmethyloxy or thietan-3-yloxy.
  • the present invention provides compounds of formula (I), wherein ring-A is phenyl, pyridinyl, pyrazolyl, thiazolyl, thienyl, 4,5,6,7-tetrahydrobenzothienyl, 2,2-difluorobenzo[d][1,3]dioxol-5- yl or thieno[2,3-b]thien-2-yl; wherein each ring-A is optionally substituted with one R 1 ′ and/or one or more R 1 .
  • ring-C is pyridinyl, pyrimidinyl, pyrazinyl, pyrazolyl or thiazolyl; wherein each ring-C is optionally substituted with one R 6 ′ or one or more R 6 .
  • the present invention provides compounds of formula (IA) and (IB) or salts thereof, wherein preferred ring-A is phenyl, pyridinyl, pyrazolyl, thiazolyl, thienyl, 4,5,6,7-tetrahydrobenzothienyl, 2,2-difluorobenzo[d][1,3]dioxol-5-yl or thieno[2,3-b]thien-2-yl; ring-B is triazolyl or pyrazinyl; ring-C is pyridinyl or pyrimidinyl, pyrazinyl, pyrazolyl or thiazolyl; D and D′ is direct bond.
  • the present invention provides compounds of formula (IA) and (IB) or salts thereof, wherein the preferred ring-A is phenyl or pyridinyl. In one embodiment, the present invention provides compounds of formula (IA) and (IB) or salts thereof, wherein the preferred ring-B is triazolyl or pyrazinyl. In one embodiment, the present invention provides compounds of formula (IA) and (IB) or salts thereof, wherein the preferred ring-C is pyridinyl, pyrimidinyl, pyrazinyl, pyrazolyl or thiazolyl.
  • the present invention provides compounds of formula (I) wherein the preferred ring-A is phenyl; ring-B is triazolyl; ring-C is pyridinyl, pyrimidinyl, pyrazinyl, pyrazolyl or thiazolyl. In one embodiment, the present invention provides compounds of formula (I) wherein the preferred ring-A is phenyl; ring-B is pyrazinyl; ring-C is pyridinyl, pyrimidinyl, pyrazinyl, pyrazolyl or thiazolyl.
  • the present invention provides compounds of formula (I) wherein the preferred ring-A is pyridinyl, pyrazolyl, thiazolyl or thienyl ring; ring-B is pyrazinyl; ring-C is pyridinyl, pyrimidinyl, pyrazinyl, pyrazolyl or thiazolyl.
  • the present invention provides compounds of formula (I) wherein the preferred ring-A is pyridinyl, pyrazolyl, thiazolyl or thienyl ring; ring-B is triazolyl; ring-C is pyridinyl, pyrimidinyl, pyrazinyl, pyrazolyl or thiazolyl.
  • the present invention provides compounds of formula (I) wherein ring-B is selected from the group consisting of ring B-1 and ring B-2; wherein # denotes the point of attachement to the amine linker part and $ denotes the point of attachement to ring-C; wherein each ring-B is optionally substituted with one or more R 5 ;
  • the present invention provides compounds of formula (I) or salts thereof wherein, ring-A represents a phenyl, pyridinyl, pyrazolyl, thiazolyl, thienyl ring, , or ; wherein * denotes the point of attachment to the carbonyl group; wherein the ring-A may be optionally substituted with one R 1 ′ and/or one or more R 1 ;
  • R 1 is selected from the group consisting of hydrogen, halogen, cyano, nitro, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C
  • the present invention provides compounds of formula (I) wherein ring-A represents a phenyl, pyridinyl, pyrazolyl, thiazolyl, thienyl ring, , or ; wherein the ring-A may be optionally substituted with one R 1 ′ and/or one or more R 1 ;
  • R 1 is selected from the group consisting of hydrogen, halogen, cyano, nitro, C 1 -C 3 -alkyl, C 1 -C 3 -haloalkyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -halocycloalkyl, C 3 -C 8 -cycloalkyl-C 1 -C 6 -alkyl, C 1 -C 6 -alkyl-C 3 -C 8 -cycloalkyl, C 1 - C 6 -haloalkyl-C 3 -C 8 -cycloalkyl, OR 4 , and
  • the present invention provides compounds of formula (I) wherein, ring-A is phenyl; wherein said phenyl ring is optionally substituted with one R 1 ′ and/or one or more R 1 ; ring-B is triazolyl; wherein said triazolyl ring is optionally substituted with one or more R 5 ; ring-C is pyridinyl, pyrimidinyl, pyrazinyl, pyrazolyl or thiazolyl; wherein each ring-C is optionally substituted with one R 6 ′ or one or more R 6 .
  • the present invention provides compounds of formula (I) wherein, ring-A is phenyl; wherein, said phenyl ring is optionally substituted with one R 1 ′ and/or one or more R 1 ; ring-B is pyrazinyl; wherein said pyrazinyl ring is optionally substituted with one or more R 5 ; ring-C is pyridinyl, pyrimidinyl, pyrazinyl, pyrazolyl or thiazolyl; wherein each ring-C is optionally substituted with one R 6 ′ or one or more R 6 .
  • the present invention provides compounds of formula (I) wherein, ring-A is pyridinyl, pyrazolyl, thiazolyl or thienyl ring; wherein each ring-A is optionally substituted with one R 1 ′ and/or one or more R 1 ; ring-B is pyrazinyl; wherein said pyrazinyl ring is optionally substituted with one or more R 5 ; ring-C is pyridinyl, pyrimidinyl, pyrazinyl, pyrazolyl or thiazolyl; wherein each ring-C is optionally substituted with one R 6 ′ or one or more R 6 In a preferred embodiment, the present invention provides compounds of formula (I) wherein, ring-A is pyridinyl, pyrazolyl, thiazolyl or thienyl ring; wherein each ring-A is optionally substituted with one R 1 ′ and/or one or more R 1 ;
  • the compounds of formula (I) are selected from: (S)-6-(5-(1-(3-chloro-5- (trifluoromethyl)benzamido)ethyl)-3-methyl-1H-1,2,4-triazol-1-yl)-N-(dimethyl(oxo)- ⁇ 6 - sulfanylidene)nicotinamide; (S)-6-(5-(1-(3-chloro-5-(trifluoromethyl)benzamido)ethyl)-3-methyl-1H- 1,2,4-triazol-1-yl)-N-(diethyl(oxo)- ⁇ 6 -sulfanylidene)nicotinamide; 6-(5-((S)-1-(3-chloro-5- (trifluoromethyl)benzamido)ethyl)-3-methyl-1H-1,2,4-triazol-1-yl)-N-(isobutyl(methyl)(
  • the compounds of the present invention can exist as one or more stereoisomers.
  • the various stereoisomers include enantiomers, diastereomers, atropisomers and geometric isomers.
  • one stereoisomer may be more active and/or may exhibit beneficial effects when enriched relative to the other stereoisomer(s) or when separated from the other stereoisomer(s). Additionally, the skilled artisan knows how to separate, enrich, and/or selectively prepare said stereoisomers.
  • the compounds of the present invention may be present as a mixture of stereoisomers, individual stereoisomers or as an optically active form.
  • An anion part of the salt in case the compound of formula (I) is a cationic or capable of forming a cation can be inorganic or organic.
  • a cation part of the salt in case the compound of formula (I) is an anionic or capable of forming anion can be inorganic or organic.
  • inorganic anion parts of the salt include but are not limited to chloride, bromide, iodide, fluoride, sulfate, phosphate, nitrate, nitrite, hydrogen carbonates and hydrogen sulfate.
  • organic anion part of the salt examples include but are not limited to formate, alkanoates, carbonates, acetates, trifluoroacetate, trichloroacetate, propionate, glycolate, thiocyanate, lactate, succinate, malate, citrates, benzoates, cinnamates, oxalates, alkylsulphates, alkylsulphonates, arylsulphonates aryldisulphonates, alkylphosphonates, arylphosphonates, aryldiphosphonates, p-toluenesulphonate, and salicylate.
  • inorganic cation parts of the salt examples include but are not limited to alkali and alkaline earth metals.
  • organic cation parts of the salt include but are not limited to pyridine, methyl amine, imidazole, benzimidazole, hitidine, phosphazene, tetramethyl ammonium, tetrabutylammonium, choline and trimethylamine.
  • Metal ions in metal complexes of the compound of formula (I) are especially ions of the elements of the second main group, especially calcium and magnesium, of the third and fourth main group, especially aluminium, tin and lead, and also of the first to eighth transition groups, especially chromium, manganese, iron, cobalt, nickel, copper, zinc and others. Particular preference is given to the metal ions of the elements of the fourth period and the first to eighth transition groups.
  • the metals can be present in the various valencies that they can assume.
  • the present invention provides a compound of formula (I) agriculturally acceptable salts, metal complexes, constitutional isomers, stereo-isomers, diastereoisomers, enantiomers, chiral isomers, atropisomers, conformers, rotamers, tautomers, optical isomers, polymorphs, geometric isomers, or N-oxides thereof and its composition with the excipient, inert carrier or any other essential ingredient such as surfactants, additives, solid diluents and liquid diluents.
  • Salts of the compounds of the formula (I) are preferably veterinary and/or agriculturally acceptable salts, preferably agriculturally acceptable salts. They can be formed in a customary manner, e.g. by reacting the compound with an acid of the anion in question if the compound of formula (I) has a basic functionality.
  • the term "N-oxide” includes any compound of formula (I) which has at least one tertiary nitrogen atom that is oxidized to an N-oxide moiety.
  • the compounds of formula (I), (including all stereoisomers, N-oxides, and salts thereof), typically exist in more than one form, and formula (I) thus includes all crystalline and non-crystalline forms of the compounds that formula (I) represents.
  • Non-crystalline forms include embodiments which are solids such as waxes and gums as well as embodiments which are liquids such as solutions and melts.
  • Crystalline forms include embodiments which represent essentially a single crystal type and embodiments which represent a mixture of polymorphs (i.e. different crystalline types).
  • polymorph refers to a particular crystalline form of a chemical compound that can crystallize in different crystalline forms, these forms having different arrangements and/or conformations of the molecules in the crystal lattice. Although polymorphs can have the same chemical composition, they can also differ in composition due to the presence or absence of co-crystallized water or other molecules, which can be weakly or strongly bound in the lattice.
  • Polymorphs can differ in such chemical, physical and biological properties as crystal shape, density, hardness, color, chemical stability, melting point, hygroscopicity, suspensibility, dissolution rate and biological availability.
  • a polymorph of a compound represented by formula (I) can exhibit beneficial effects (e.g., suitability for preparation of useful formulations, improved biological performance) relative to another polymorph or a mixture of polymorphs of the same compound represented by formula (I).
  • Preparation and isolation of a particular polymorph of a compound represented by formula (I) can be achieved by methods known to those skilled in the art including, for example, crystallization using selected solvents and temperatures.
  • the present invention provides a process for preparing the compounds of formula (I) or agriculturally acceptable salts, Formula (I)
  • the compounds of the present invention as defined by formula (I) and/or in table (I) may be prepared, basically in a known manner, in a variety of ways as described in the schemes.
  • Compounds of the present invention can be made as shown in the following schemes, in which, unless otherwise stated, the definition of each variable is as defined above for compounds of formula (I).
  • Carboxylic acid of formula (b) and compounds of formula (d) are commercially available or may be synthesized by following an analogous procedure as disclosed in WO2019197468, WO2021013720, J. Org. Chem., 2005, 70, 6904-6906, Chem. Eur. J.2021, 27, 17293–17321, J. Am. Chem. Soc.2020, 142, 15445– 15453.
  • Compounds of formula (a) can be prepared as shown in the scheme 2 (by following an analogous procedure as disclosed in WO2019196468 & WO2017192385) wherein R 2 , R 3a and R 3b , R 5 , ring-B, and ring-C are as described previously.
  • compounds of formula (r) can also be synthesized through a Suzuki coupling by reacting compounds of formula (p) with compounds of formula (q-1) (wherein the leaving group BA is selected from boronic acids or pinacol boronate ester or triflates) in the presence of a palladium catalyst for example tetrakis(triphenylphosphine)palladium(0), Palladiun Chloride (PdCl2), Palladium acetate (Pd(OAc)2), 1,1 'bis(diphenylphosphino)- ferrocene)dichloropalladium-dichloromethane complex and the like, in the presence of a base, such as sodium carbonate, potassium phosphate, cesium fluoride and the like, in a solvent or a solvent mixture, for example a mixture of 1 ,2-dimethoxyethane and water, dioxane and water, ethanol and water or N,N- dimethylformamide (DMF)
  • the reaction temperature can preferentially range from 25 °C to the boiling point of the reaction mixture.
  • Suzuki reactions are well known in the literature for example Synthesis, 2007, 393-399, J. Org. Chem., 2007, 72, 4067-4072.
  • R 6 is selected from an ester if D is a CO linker, and R 6 is selected from alkyl-alkoxy if D is a CH 2 linker.
  • Scheme 4 The compounds of formula (c) wherein R 6 is selected from tertbutyl ester, were hydrolyzed to form compounds of formula (m) under acidic conditions by using trifluoracetic acid or phosphoric acid and the like, in a suitable solvent such as dichloromethane (DCM), tetrahydrofuran (THF) and the like, at a temperature ranging from 0 to 40 °C.
  • DCM dichloromethane
  • THF tetrahydrofuran
  • sulfoximines of formula (d) are reacted with sulfoximines of formula (d), in the presence of a suitable amide coupling reagents such as propylphosphonic anhydride (T3P), 1-[Bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxid hexafluorophosphate (HATU), N,N′-dicyclohexylcarbodiimide (DCC), Hydroxybenzotriazole (HOBT) and the like, a suitable base such as triethyl amine, N,N-diisopropylethylamine (DIPEA) and the like, in a suitable solvent such as N,N-dimethylformamide (DMF), acetonitrile and the like, at a temperature ranging from 0 to 100 °C to provide acyl sulfoximine derivatives of formula (I).
  • T3P propylphosphonic
  • methylene linker containing sulfoximine derivatives can be synthesized following scheme 4.
  • R 6 is selected from alkyl-alkoxy
  • BBr 3 boron tribromide
  • Compounds of formula (d) can be N-alkylated with compounds of formula (d) in a suitable solvent such as tetrahydrofuran (THF), N,N-dimethylformamide (DMF), acetonitrile and the like, in a suitable base such as potassium carbonate (K 2 CO 3 ), potassium hydroxide (KOH), sodium bicarbonate (NaHCO 3 ) and the like to get compounds of formula (I).
  • a suitable solvent such as tetrahydrofuran (THF), N,N-dimethylformamide (DMF), acetonitrile and the like
  • a suitable base such as potassium carbonate (K 2 CO 3 ), potassium hydroxide (KOH), sodium bicarbonate (NaHCO 3 ) and the like to get compounds of formula (I).
  • K 2 CO 3 potassium carbonate
  • KOH potassium hydroxide
  • NaHCO 3 sodium bicarbonate
  • Carboxylic acid of formula (b) are subjected to an amide coupling with compounds of formula (e-1) in the presence of a suitable coupling agents such as propylphosphonic anhydride (T3P), 1-[Bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxid hexafluorophosphate (HATU), N,N′-dicyclohexylcarbodiimide (DCC), Hydroxybenzotriazole (HOBT) and the like, a suitable base such as triethyl amine, N,N-diisopropylethylamine (DIPEA) and the like, in a suitable solvent such as, N,N-dimethylformamide (DMF), acetonitrile and the like, at a temperature ranging from 0 to 100 °C to provide compounds of formula (n).
  • T3P propylphosphonic anhydride
  • HATU 1-[Bis(
  • Carboxylic acid intermediates of formula (b-2) can be prepared by following the synthetic scheme 7, wherein ring-A is always substituted with R 1 ′ and optionally substituted with R 1 . Both R 1 and R 1 ′ are as described previously.
  • Compounds of formula (b) can be converted to compounds of formula (b-1) through a Pd- catalyzed C-N coupling with compounds of formula (d) in the presence of a suitable coupling reagent such as palladium acetate, xanthphos and the like, a suitable base such as potassium carbonate (K 2 CO 3 ), potassium phosphate (K 3 PO 4 ) and the like, in a suitable solvent such as toluene, acetonitrile, N,N- dimethylformamide (DMF) and the like, at a temperature ranging from 100-120 °C.
  • a suitable coupling reagent such as palladium acetate, xanthphos and the like
  • a suitable base such as potassium carbon
  • N-arylated sulfoximines can also be synthesized through inexpensive and mild methods for copper-catalysed N- arylations of sulfoximines described in the literature for example in the J. Org. Chem., 2005, 70, 6904- 6906.
  • Compounds of formula (b-1) are hydrolyzed under basic condition to get compounds of formula (b- 2).
  • Scheme 8 The substituted hydrazine intermediates of formula (h-1) are commercially available or may be prepared by following scheme 8 (see also J. Heterocyclic chem., 49, 442, 2012), wherein ring-C is selected from pyridine or pyrimidine (e.g x: CH for pyridine & X: N for pyrimidine).
  • compounds of formula (5) are reacted with a compound of formula (b) (commercially available aryl or heteroaryl carboxylic acid or a synthesized one using the procedure known from the literature), in the presence of suitable amide coupling reagents such as propylphosphonic anhydride (T3P), 1-[Bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5- b]pyridinium 3-oxid hexafluorophosphate (HATU), N,N′-dicyclohexylcarbodiimide (DCC), Hydroxybenzotriazole (HOBT) and the like, a suitable base such as triethyl amine, N,N- diisopropylethylamine (DIPEA) and the like, in a suitable solvent such as, N,N-dimethylformamide (DMF), acetonitrile and the like, at a temperature ranging from 0 to 100 °C to provide compounds of
  • the compounds of formula (6) undergo a metal catalysed C-N coupling with compounds of formula (d) in the presence of suitable coupling reagents such as palladium acetate, xanthphos and the like, a suitable base such as potassium carbonate (K 2 CO 3 ), sodium carbonate (Na 2 CO 3 ), cesium carbonate (Cs 2 CO 3 ) and the like, in a suitable solvent such as toluene, acetonitrile, N,N-dimethylformamide (DMF) at a temperature ranging from 100-120 °C to provide compounds of formula (I) (compounds 9-30, 44-102, 116-139, 146- 162, 174-186, 190-194, 199, 216-230).
  • suitable coupling reagents such as palladium acetate, xanthphos and the like
  • a suitable base such as potassium carbonate (K 2 CO 3 ), sodium carbonate (Na 2 CO 3 ), cesium carbonate (Cs
  • Cross-benzoin condensations are done in the usual way by employing an organocatalyst such as a triazolium salt or a thiazolium salt in the presence of a base such as potassium tert-butoxide or diisopropyldiethylamine in a suitable solvent such as dichloromethane, tetrahydrofuran and the like, at a temperature ranging from 0-20 °C and the boiling point of the solvent.
  • a base such as potassium tert-butoxide or diisopropyldiethylamine
  • a suitable solvent such as dichloromethane, tetrahydrofuran and the like
  • This oxidation can involve, for instance, Dess–Martin periodinane (DMP), SO3-pyridine in the presence of dimethyl sulfoxide (DMSO) and a suitable base such as triethylamine, sodium hypochlorite and the like, in the presence of a suitable catalyst such as (2,2,6,6- Tetramethylpiperidin-1-yl)oxyl, (2,2,6,6-tetramethylpiperidin-1-yl)oxidanyl (TEMPO) and the like.
  • DMP Dess–Martin periodinane
  • DMSO dimethyl sulfoxide
  • a suitable base such as triethylamine, sodium hypochlorite and the like
  • a suitable catalyst such as (2,2,6,6- Tetramethylpiperidin-1-yl)oxyl, (2,2,6,6-tetramethylpiperidin-1-yl)oxidanyl (TEMPO) and the like.
  • TEMPO 2,2,6,6- Tetramethylpiperidin-1-yl
  • compounds of formula (10) undergo metal catalysed C-N coupling with compounds of formula (d) in the presence of a suitable coupling reagent such as palladium acetate, xanthphos and the like, a suitable base such as potassium carbonate (K 2 CO 3 ), sodium carbonate (Na 2 CO 3 ), cesium carbonate (Cs 2 CO 3 ) and the like, in a suitable solvent such as toluene, acetonitrile or N,N-dimethylformamide (DMF) and the like, at a temperature ranging from 100-120 °C, to provide compounds of formula (11).
  • a suitable coupling reagent such as palladium acetate, xanthphos and the like
  • a suitable base such as potassium carbonate (K 2 CO 3 ), sodium carbonate (Na 2 CO 3 ), cesium carbonate (Cs 2 CO 3 ) and the like
  • a suitable solvent such as toluene, acetonitrile or N,N-di
  • compounds of formula (6) are reacted with the compounds of formula (d) (commercially available aryl or heteroaryl carboxylic acid or synthesized using the procedure known from literature), in the presence of suitable amide coupling reagents such as propylphosphonic anhydride (T3P), 1-[Bis(dimethylamino)methylene]-1H- 1,2,3-triazolo[4,5-b]pyridinium 3-oxid hexafluorophosphate (HATU), N,N′-dicyclohexylcarbodiimide (DCC), Hydroxybenzotriazole (HOBT) and the like, a suitable base such as triethyl amine, N,N- diisopropylethylamine (DIPEA) and the like, in a suitable solvent such as, N,N-dimethylformamide (DMF), acetonitrile and the like, at a temperature ranging from 0 to 100 °C, to provide compounds of formula (I) (T3P),
  • the present invention provides compounds of formula (I), wherein ring-A is selected from: a.
  • the present invention provides compounds of formula (I), wherein R 2 is selected from: a. hydrogen, C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl or C 1 -C 6 -haloalkyl; or b. hydrogen, C 1 -C 3 -alkyl or C 1 -C 3 -haloalkyl; or c. hydrogen, methyl, ethyl or (n or iso) propyl; or d.
  • the present invention provides compounds of formula (I), wherein R 3a is hydrogen.
  • the present invention provides compounds of formula (I), wherein R 3b is selected from: a. C 1 -C 6 -alkyl; or b. C 1 -C 3 -alkyl; or c. methyl, ethyl or propyl; or d. methyl.
  • the present invention provides compounds of formula (I), wherein ring-B is selected from: a. ; or b. ring B-1 is triazolyl and ring B-2 is pyrazinyl; or c. ring B-1 is optionally substituted with one or more R 5 ; or d.
  • ring B-2 is optionally substituted with one or more R 5 .
  • the present invention provides compounds of formula (I), wherein ring-C is selected from: a. phenyl or 5-6 membered heteroaromatic ring, which are, independently of each other, substituted with one R 6 ′ or one or more R 6 ; or b. pyridinyl, pyrimidinyl, pyrazinyl, pyrazolyl or thiazolyl, which are, independently of each other, substituted with one R 6 ′ or one or more R 6 ; or c.
  • the present invention provides compounds of formula (I), wherein R 1 is selected from: a.
  • each group of R 1 is optionally substituted with one or more groups consisting of CN and C 1 -C 3 -alkyl; or d.
  • the present invention provides compounds of formula (I), wherein R 7a and R 8a is independently selected from: a. C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 3 -C 8 -cycloalkyl, C 6 -C 10 -aryl, C 6 -C 10 -aryl-C 1 -C 6 -alkyl, C 3 -C 8 - heterocyclyl, C 3 -C 8 -heterocyclyl-C 1 -C 6 -alkyl or NR c R d ; b.
  • the present invention provides compounds of formula (I), wherein R 7b and R 8b is independently selected from: a.
  • the present invention provides compounds of formula (I), wherein R c and R d is independently selected from: a. hydrogen and/or C 1 -C 6 -alkyl; or b. C 1 -C 3 -alkyl; c. methyl, ethyl or (n or iso) propyl.
  • the present invention provides compounds of formula (I), wherein R 7a and R 7b substituents together with the atom to which they are attached may form: a.
  • the present invention provides compounds of formula (I), wherein R 8a and R 8b substituents together with the atom to which they are attached may form: a. 3- to 6-membered non aromatic heterocyclic ring; or b. tetrahydrothiophenyl or thietanyl.
  • the present invention provides compounds of formula (I), wherein R 6 is a.
  • the present invention provides compounds of formula (I), wherein R′ is a. hydrogen, C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl or C 3 -C 8 -cycloalkyl; or b. hydrogen, C 1 -C 3 -alkyl, C 2 -C 4 -alkenyl or C 3 -C 6 -cycloalkyl; or c. hydrogen, methyl, ethyl, (n or iso) propyl, cyclopropyl or cyclobutyl.
  • the present invention provides compounds of formula (I), wherein R′′ is a.
  • the present invention provides compounds of formula (I), wherein ring-A is selected from A-1 to A-66.
  • the compounds of formula (I), and the intermediates thereof may be present either in pure form or as mixtures of different possible isomeric forms such as stereoisomers or constitutional isomers.
  • the various stereoisomers include enantiomers, diastereomers, chiral isomers, atropisomers, conformers, rotamers, tautomers, optical isomers, polymorphs, and geometric isomers.
  • the compounds of formula (I) and intermediates thereof can also exist in one or more geometric isomer forms depending on the relative position (syn/anti or cis/trans) of the substituents.
  • the invention thus relates equally to all syn/anti (or cis/trans) isomers and to all possible syn/anti (or cis/trans) mixtures, in all proportions.
  • the syn/anti (or cis/trans) isomers can be separated according to general methods, which are known per se by the man ordinary skilled in the art.
  • the present invention provides a process for the preparation of the compound of formula (I) or the salts thereof.
  • the compounds of formula (I), including their stereoisomers, salts, and N-oxides, and their precursors in the synthesis process, can be prepared by the methods described above. If individual compounds can not be prepared via the above-described routes, they can be prepared by derivatization of other compounds (I) or the respective precursor or by customary modifications of the synthesis routes described. For example, in individual cases, certain compounds of formula (I) can advantageously be prepared from other compounds of formula (I) by derivatization, e.g. by ester hydrolysis, amidation, esterification, ether cleavage, olefination, reduction, oxidation and the like, or by customary modifications of the synthesis routes described.
  • reaction mixtures are worked up in a customary manner, e.g. by mixing with water, separating the phases and, if appropriate, chromatographic purification of the crude products.
  • Some of the intermediates and end products are obtained in the form of colourless or slightly brownish viscous oils which are purified or freed from volatile components under reduced pressure and at moderately elevated temperature. If the intermediates and end products are obtained as solids, purification can also be carried out by recrystallization or digestion. If individual compounds (I) cannot be obtained by the routes described above, they can be prepared by derivatization of other compounds (I).
  • the present invention provides a composition for controlling or preventing invertebrate pests.
  • the composition comprises a biologically effective amount of the compound of formula (I) agriculturally acceptable salts, stereo-isomers, diastereomers, enantiomers, tautomers, metal complexes, polymorphs, or N-oxides thereof and at least one additional component selected from the group consisting of surfactants and auxiliaries.
  • the composition additionally comprises at least one additional biologically active and compatible compound selected from fungicides, insecticides, nematicides, acaricides, biopesticides, herbicides, plant growth regulators, antibiotics, fertilizers or nutrients.
  • the present invention provides a compound of formula (I) or its N-oxides and salts into customary types of agrochemical compositions, e.
  • composition types are suspensions (e.g. SC, OD, FS), emulsifiable concentrates (e.g. EC), emulsions (e.g. EW, EO, ES, ME), capsules (e.g. CS, ZC), pastes, pastilles, wettable powders or dusts (e.g. WP, SP, WS, DP, DS), pressings (e.g. BR, TB, DT), granules (e.g.
  • compositions types are defined in the "Catalogue of pesticide formulation types and international coding system", in the Technical Monograph No.2, 6 th Ed. May 2008, CropLife International.
  • the compositions are prepared in a known manner, such as described by Mollet and Grubemann, Formulation technology, Wiley VCH, Weinheim, 2001; or Knowles, New developments in crop protection product formulation or in Agrow Reports DS243, T and in F Informa, London, 2005.
  • auxiliaries are solvents, liquid carriers, solid carriers or fillers, surfactants, dispersants, emulsifiers, wetters, adjuvants, solubilizers, penetration enhancers, protective colloids, adhesion agents, thickeners, humectants, repellents, attractants, feeding stimulants, compatibilizers, bactericides, anti-freezing agents, anti-foaming agents, colorants, tackifiers or binders.
  • Suitable solvents and liquid carriers are water and organic solvents, such as mineral oil fractions of medium to high boiling point, e.g. kerosene, diesel oil; oils of vegetable or animal origin; aliphatic, cyclic and aromatic hydrocarbons, e. g.
  • Suitable solid carriers or fillers are mineral earths, e.g.
  • silicates silica gels, talc, kaolins, limestone, lime, chalk, clays, dolomite, diatomaceous earth, bentonite, calcium sulfate, magnesium sulfate, magnesium oxide; polysaccharide powders, e.g. cellulose, starch; fertilizers, e.g. ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas; products of vegetable origin, e.g. cereal meal, tree bark meal, wood meal, nutshell meal, and mixtures thereof.
  • Suitable surfactants are surface-active compounds, such as anionic, cationic, nonionic and amphoteric surfactants, block polymers, polyelectrolytes, and mixtures thereof. Such surfactants can be used as emusifier, dispersant, solubilizer, wetter, penetration enhancer, protective colloid, or adjuvant. Examples of surfactants are listed in McCutcheon′s, Vol.1: Emulsifiers and Detergents, McCutcheon′s Directories, Glen Rock, USA, 2008 (International Ed. or North American Ed.).
  • Suitable anionic surfactants are alkali, alkaline earth or ammonium salts of sulfonates, sulfates, phosphates, carboxylates, and mixtures thereof.
  • sulfonates are alkylarylsulfonates, diphenylsulfonates, alpha-olefin sulfonates, lignine sulfonates, sulfonates of fatty acids and oils, sulfonates of ethoxylated alkylphenols, sulfonates of alkoxylated arylphenols, sulfonates of condensed naphthalenes, sulfonates of dodecyl and tridecylbenzenes, sulfonates of naphthalenes and alkylnaphthalenes, sulfosuccinates or sulfosuccinamates.
  • sulfates are sulfates of fatty acids and oils, of ethoxylated alkylphenols, of alcohols, of ethoxylated alcohols, or of fatty acid esters.
  • phosphates are phosphate esters.
  • carboxylates are alkyl carboxylates, and carboxylated alcohol or alkylphenol ethoxylates.
  • Suitable nonionic surfactants are alkoxylates, N-subsituted fatty acid amides, amine oxides, esters, sugar- based surfactants, polymeric surfactants, and mixtures thereof.
  • alkoxylates are compounds such as alcohols, alkylphenols, amines, amides, arylphenols, fatty acids or fatty acid esters which have been alkoxylated with 1 to 50 equivalents.
  • Ethylene oxide and/or propylene oxide may be employed for the alkoxylation, preferably ethylene oxide.
  • N-subsititued fatty acid amides are fatty acid glucamides or fatty acid alkanolamides.
  • esters are fatty acid esters, glycerol esters or monoglycerides.
  • sugarbased surfactants are sorbitans, ethoxylated sorbitans, sucrose and glucose esters or alkylpolyglucosides.
  • polymeric surfactants are homeor copolymers of vinylpyrrolidone, vinylalcohols, or vinylacetate.
  • Suitable cationic surfactants are quaternary surfactants, for example quaternary ammonium compounds with one or two hydrophobic groups, or salts of long-chain primary amines.
  • Suitable amphoteric surfactants are alkylbetains and imidazolines.
  • Suitable block polymers are block polymers of the A-B or A-B-A type comprising blocks of polyethylene oxide and polypropylene oxide, or of the A-B-C type comprising alkanol, polyethylene oxide and polypropylene oxide.
  • Suitable polyelectrolytes are polyacids or polybases.
  • polyacids are alkali salts of polyacrylic acid or polyacid comb polymers.
  • polybases are polyvinylamines or polyethyleneamines.
  • Suitable adjuvants are compounds, which have a neglectable or even no pesticidal activity themselves, and which improve the biological performance of the compound I on the target. Examples are surfactants, mineral or vegetable oils, and other auxilaries. Further examples are listed by Knowles, Adjuvants and additives, in the Agrow Reports DS256 and in Tand F Informa UK, 2006, chapter 5.
  • Suitable thickeners are polysaccharides (e.g. xanthan gum, carboxymethylcellulose), anorganic clays (organically modified or unmodified), polycarboxylates, and silicates.
  • Suitable bactericides are bronopol and isothiazolinone derivatives such as alkylisothiazolinones and benzisothiazolinones.
  • Suitable anti- freezing agents are ethylene glycol, propylene glycol, urea and glycerin.
  • Suitable anti-foaming agents are silicones, long chain alcohols, and salts of fatty acids.
  • Suitable colorants e.g. in red, blue, or green
  • examples are inorganic colorants (e.g. iron oxide, titan oxide, iron hexacyanoferrate) and organic colorants (e.g. alizarin-, azoand phthalocyanine colorants).
  • Suitable tackifiers or binders are polyvinylpyrrolidone, polyvinylacetates, polyvinyl alcohols, polyacrylates, biological or synthetic waxes, and cellulose ethers.
  • composition types and their preparation are: i) Water-soluble concentrates (SL, LS) 10-60 wt% of a compound (I) or an N-oxide or salt thereof and 5-15 wt% wetting agent (e.g. alcohol alkoxylates) are dissolved in water and/or in a water-soluble solvent (e.g. alcohols) up to 100 wt%. The active substance dissolves upon dilution with water.
  • Dispersible concentrates 5-25 wt% of a compound (I) or an N-oxide or salt thereof and 1-10 wt% dispersant (e. g. polyvinylpyrrolidone) are dissolved in up to 100 wt% organic solvent (e.g. cyclohexanone). Dilution with water gives a dispersion.
  • Emulsifiable concentrates EC 15-70 wt% of a compound I or an N-oxide or salt thereof and 5-10 wt% emulsifiers (e.g.
  • Emulsions (EW, EO, ES) 5-40 wt% of a compound (I) or an N-oxide or salt thereof and 1 -10 wt% emulsifiers (e.g. calcium dodecylbenzenesulfonate and castor oil ethoxylate) are dissolved in 20-40 wt% water-insoluble organic solvent (e.g. aromatic hydrocarbon).
  • Suspensions SC, OD, FS
  • 20-60 wt% of a compound (I) or an N-oxide or salt thereof are comminuted with the addition of 2-10 wt% dispersants and wetting agents (e.g. sodium lignosulfonate and alcohol ethoxylate), 0,1 -2 wt% thickener (e.g. xanthan gum) and up to 100 wt% water to give a fine active substance suspension.
  • dispersants and wetting agents e.g. sodium lignosulfonate and alcohol ethoxylate
  • 0,1 -2 wt% thickener e.g. xanthan gum
  • WG, SG Water-dispersible granules and water-soluble granules (WG, SG) 50-80 wt% of a compound (I) or an N-oxide or salt thereof are ground finely with the addition of up to 100 wt% dispersants and wetting agents (e.g. sodium lignosulfonate and alcohol ethoxylate) and prepared as water-dispersible or water-soluble granules by means of technical appliances (e. g. extrusion, spray tower, fluidized bed).
  • dispersants and wetting agents e.g. sodium lignosulfonate and alcohol ethoxylate
  • Dilution with water gives a stable dispersion or solution of the active substance.
  • WP, SP, WS Water-dispersible powders and water-soluble powders 50-80 wt% of a compound (I) or an N-oxide or salt thereof are ground in a rotor-stator mill with the addition of 1 -5 wt% dispersants (e.g. sodium lignosulfonate), 1-3 wt% wetting agents (e.g. alcohol ethoxylate) and up to 100 wt% solid carrier, e.g. silica gel. Dilution with water gives a stable dispersion or solution of the active substance.
  • dispersants e.g. sodium lignosulfonate
  • wetting agents e.g. alcohol ethoxylate
  • solid carrier e.g. silica gel
  • Microcapsules An oil phase comprising 5-50 wt% of a compound I or an N-oxide or salt thereof, 0-40 wt% water insoluble organic solvent (e.g. aromatic hydrocarbon), 2-15 wt% acrylic monomers (e.g.
  • methylmethacrylate, methacrylic acid and a dior triacrylate are dispersed into an aqueous solution of a protective colloid (e.g. polyvinyl alcohol). Radical polymerization initiated by a radical initiator results in the formation of poly(methyl acrylate) microcapsules.
  • a protective colloid e.g. polyvinyl alcohol
  • Radical polymerization initiated by a radical initiator results in the formation of poly(methyl acrylate) microcapsules.
  • an oil phase comprising 5-50 wt% of a compound of formula (I), according to the present invention, 0-40 wt% water insoluble organic solvent (e.g. aromatic hydrocarbon), and an isocyanate monomer (e.g. diphenylmethene-4,4′-diisocyanatae) are dispersed into an aqueous solution of a protective colloid (e.g. polyvinyl alcohol).
  • a polyamine e.g. hexamethylenediamine
  • the monomers amount to 1 - 10 wt%.
  • the wt% relate to the total CS composition
  • Dustable powders (DP, DS) 1-10 wt% of a compound I or an N-oxide or salt thereof are ground finely and mixed intimately with up to 100 wt% solid carrier, e.g. finely divided kaolin.
  • Granules (GR, FG) 0.5-30 wt% of a compound I or an N-oxide or salt thereof is ground finely and associated with up to 100 wt% solid carrier (e.g. silicate).
  • Ultra-low volume liquids 1-50 wt% of a compound I or an N-oxide or salt thereof are dissolved in up to 100 wt% organic solvent, e.g. aromatic hydrocarbon.
  • the compositions types i) to xiii) may optionally comprise further auxiliaries, such as 0.1-1 wt% bactericides, 5-15 wt% anti-freezing agents, 0.1-1 wt% anti-foaming agents, and 0.1 -1 wt% colorants.
  • the present invention provides agrochemical compositions with the compound of formula (I), which comprise an active substance content between 0.01 and 95% by weight, preferably between 0.1 and 90%, and more preferably between 1 and 70 %, in particular between 10 and 60 by weight of active substance.
  • the active substances are employed in a purity from 90% to 100%, preferably from 95% to 100% (according to NMR spectrum).
  • Water-soluble concentrates (LS), Suspoemulsions (SE), flowable concentrates (FS), powders for dry treatment (DS), water-dispersible powders for slurry treatment (WS), water-soluble powders (SS), emulsions (ES), emulsifiable concentrates (EC) and gels (GF) are usually employed for the purposes of treatment of plant propagation materials, particularly seeds.
  • the compositions in question give, after two- to-tenfold dilution, active substance concentrations from 0.01 to 60% by weight, preferably from 0.1 to 40% by weight, in the ready-to-use preparations. Applications can be carried out before or during sowing.
  • Methods for applying or treating compounds of formula (I) and compositions thereof, respectively, on to plant propagation material, especially seeds include dressing, coating, pelleting, dusting, soaking and in- furrow application methods of the propagation material.
  • the compound of formula (I) or the compositions thereof, respectively are applied on to the plant propagation material by a method such that the germination is not induced, e. g. by seed dressing, pelleting, coating and dusting.
  • the amounts of active substances applied are, depending on the kind of effect desired, from 0.001 to 2 kg per ha, preferably from 0.005 to 2 kg per ha, more preferably from 0.02 to 0.9 kg per ha, in particular from 0.05 to 0.75 kg per ha.
  • amounts of active substance from 0.1 to 1000 g, preferably from 1 to 500 g, more preferably from 5 to 200 g and most preferably from 10 to 100 g, per 100 kilogram of plant propagation material (preferably seed) are generally required.
  • the amount of active substance applied depends on the kind of application area and on the desired effect. Amounts customarily applied in the protection of materials are from 0.001 g to 2 kg, preferably from 0.005 g to 1 kg, of active substance per cubic meter of treated material.
  • oils, wetters, adjuvants, fertilizer, or micronutrients, and other pesticides may be added to the active substances or the compositions comprising them as premix or, if appropriate, not until immediately prior to use (tank mix).
  • pesticides e.g. herbicides, insecticides, fungicides, growth regulators, safeners, antibiotics, fertilizers, nutrients and biostimulants
  • These agents can be admixed with the compositions according to the present invention in a weight ratio of 1:100 to 100:1, preferably 1:10 to 10:1.
  • the user can apply the composition according to the present invention usually from a predosage device, a knapsack sprayer, a spray tank, a spray plane, or an irrigation system.
  • the agrochemical composition is made up with water, buffer, and/or further auxiliaries to the desired application concentration and the ready-to-use spray liquor or the agrochemical composition according to the present invention is thus obtained.
  • 20 to 6000 liters, preferably 35 to 1000 litres, more preferably 50 to 500 liters, of the ready-to-use spray liquor are applied per hectare of the agricultural useful area.
  • individual components of the composition according to the present invention such as parts of a kit or parts of a binary or ternary mixture may be mixed by the user himself in a spray tank and further auxiliaries may be added, if appropriate.
  • the compounds and compositions of the present invention are thus useful agronomically for protecting field crops from phytophagous invertebrate pests, and also nonagronomically for protecting other horticultural crops and plants from phytophagous invertebrate pests.
  • This utility includes protecting crops and other plants (i.e. both agronomic and nonagronomic) that contain genetic material introduced by genetic engineering (i.e. transgenic) or modified by mutagenesis to provide advantageous traits.
  • the compounds of the present invention are characterized by favorable metabolic and/or soil residual patterns and exhibit activity controlling a wide spectrum of agronomic and non-agronomic invertebrate pests.
  • invertebrate pest control means inhibition of invertebrate pest development (including mortality) that causes significant reduction in feeding or other injury or damage caused by the pest; related expressions are defined analogously.
  • invertebrate pest includes arthropods, gastropods and nematodes of economic importance as pests.
  • arthropod includes insects, mites, spiders, scorpions, centipedes, millipedes, pill bugs and symphylans.
  • gastropod includes snails, slugs and other stylommatophora.
  • nematode includes all of the helminths, such as: roundworms, heartworms, and phytophagous nematodes (Nematoda), flukes (Tematoda), acanthocephala, and tapeworms (Cestoda). Those skilled in the art will recognize that not all compounds are equally effective against all pests.
  • the compounds of the present invention display activity against economically important agronomic, forest, greenhouse, nursery, ornamentals, turfgrass, food and fiber, public and animal health, domestic and commercial structure, household, and stored product pests.
  • These include larvae of the order Lepidoptera, such as armyworms, cutworms, loopers, and heliothines in the family Noctuidae (e.g., fall armyworm (Spodoptera fugiperda J. E.
  • earwigs from the family Forficulidae e.g., European earwig (Forficula auricularia Linnaeus), black earwig (Chelisoches mono Fabricius)
  • adults and nymphs of the orders Hemiptera and Homoptera such as, plant bugs from the family Miridae, cicadas from the family Cicadidae, leafhoppers (e.g.
  • insects are also included are adults and larvae of the order Acari (mites) such as spider mites and red mites in the family Tetranychidae (e.g., European red mite (Panonychus ulmi Koch), two spotted spider mite (Tetranychus urticae Koch), McDaniel mite (Tetranychus mcdanieli McGregor)), flat mites in the family Tenuipalpidae (e.g., citrus flat mite (Brevipalpus lewisi McGregor)), rust and bud mites in the family Eriophyidae and other foliar feeding mites and mites important in human and animal health, i.e.
  • Tetranychidae e.g., European red mite (Panonychus ulmi Koch), two spotted spider mite (Tetranychus urticae Koch), McDaniel mite (Tetranychus mcdaniel
  • Additional arthropod pests covered include: spiders in the order Araneae such as the brown recluse spider (Loxosceles reclusa Gertsch and Mulaik) and the black widow spider (Latrodectus mactans Fabricius), and centipedes in the order Scutigeromorpha such as the house centipede (Scutigera coleoptrata Linnaeus).
  • spiders in the order Araneae such as the brown recluse spider (Loxosceles reclusa Gertsch and Mulaik) and the black widow spider (Latrodectus mactans Fabricius)
  • centipedes in the order Scutigeromorpha such as the house centipede (Scutigera coleoptrata Linnaeus).
  • Activity also includes members of the Classes Nematoda, Cestoda, Trematoda, and Acanthocephala including economically important members of the orders Strongylida, Ascaridida, Oxyurida, Rhabditida, Spirurida, and Enoplida such as but not limited to economically important agricultural pests (i.e. root knot nematodes in the genus Meloidogyne, lesion nematodes in the genus Pratylenchus, stubby root nematodes in the genus Trichodorus, etc.) and animal and human health pests (i.e.
  • the compounds of the present invention show particularly high activity against pests in the order Lepidoptera (e.g., Alabama argillacea Hubner (cotton leaf worm), Archips argyrospila Walker (fruit tree leaf roller), A.
  • Lepidoptera e.g., Alabama argillacea Hubner (cotton leaf worm), Archips argyrospila Walker (fruit tree leaf roller), A.
  • E. Smith (fall armyworm), Trichoplusia ni H ⁇ bner (cabbage looper) and Tula absolutea Meyrick (tomato leafminer)).
  • Compounds of the present invention also have commercially significant activity on members from the order Homoptera including: Acyrthisiplionpisum Harris (pea aphid), Aphis craccivora Koch (cowpea aphid), Aphis fabae Scopoli (black bean aphid), Aphis gossypii Glover (cotton aphid, melon aphid), Aphis pomi De Geer (apple aphid), Aphis spiraecola Patch (spirea aphid), Aulacorthum solani Kaltenbach (foxglove aphid), Chaetosiphon fragaefolii Cockerell (strawberry aphid), Diuraphis noxia Kurdjumov/Mordvilko (Russian wheat a
  • Thysanoptera e.g., Frankliniella occidentalis Pergande (western flower thrip), Scirthoth ⁇ ps citri Moulton (citrus thrip), Sericothrips variabilis Beach (soybean thrip), and Thrips tabaci
  • the compounds of formula (I), their N-oxides, their stereo-isomers, their polymorphs and their salts are especially suitable for efficiently combating the following pests: Insects from the order of the lepidopterans (Lepidoptera), for example Agrotis ypsilon, Agrotis segetum, Alabama argillacea, Anticarsia gemmatalis, Argyresthia conjugella, Autographa gamma, Bupalus piniarius, Cacoecia murinana, Capua reticulana, Cheimatobia brumata, Chilo infuscatellus, Choristoneura fumiferana, Choristoneura occidentalis, Cirphis unipuncta, Cydia pomonella, Dendrolimus pini, Diaphania nitidalis, Diatraea grandiosella, Earias insulana, Earias vittella, Elasmopalpus lignosellus
  • Calotermes flavicollis Leucotermes flavipes, Heterotermes aureus, Reticulitermes flavipes, Reticulitermes virginicus, Reticulitermes lucifugus, Reticulitermes santonensis, Reticulitermes grassei, Termes natalensis, and Coptotermes formosanus; cockroaches (Blattaria Blattodea), e.g.
  • Blattella germanica Blattella asahinae, Periplaneta americana, Periplaneta japonica, Periplaneta brunnea, Periplaneta fuligginosa, Periplaneta australasiae, and Blatta orientalis; ants, bees, wasps, sawflies (Hymenoptera), e.g.
  • Atta cephalotes Atta capiguara, Atta cephalotes, Atta laevigata, Atta robusta, Atta sexdens, Atta texana, Crematogaster spp., Hoplocampa minuta, Hoplocampa testudinea, Lasius niger, Monomorium pharaonis, Solenopsis geminata, Solenopsis invicta, Solenopsis richteri, Solenopsis xyloni, Pogonomyrmex barbatus, Pogonomyrmex californicus, Pheidole megacephala, Dasymutilla occidentalis, Bombus spp., Vespula squamosa, Paravespula vulgaris, Paravespula pennsylvanica, Paravespula germanica, Dolichovespula maculata, Vespa crabro, Polistes rubiginosa, Campo
  • Narceus spp. Earwigs (Dermaptera), e.g. forficula auricularia, lice (Phthiraptera), e.g. Pediculus humanus capitis, Pediculus humanus corporis, Pthirus pubis, Haematopinus eurysternus, Haematopinus suis, Linognathus vituli, Bovicola bovis, Menopon allinae, Menacanthus stramineus and Solenopotes capillatus. Collembola (springtails), e.g. Onychiurus ssp.
  • the compounds of formula (I) of the present invention are also suitable for controlling Nematodes: plant parasitic nematodes such as root knot nematodes, Meloidogyne hapla, Meloidogyne incognita, Meloidogyne javanica, and other Meloidogyne species; cyst-forming nematodes, Globodera rostochiensis and other Globodera species; Heterodera avenae, Heterodera glycines, Heterodera schachtii, Heterodera trifolii, and other Heterodera species; Seed gall nematodes, Anguina species; Stem and foliar nematodes, Aphelenchoides species; Sting nematodes, Belonolaimus longicaudatus and other Belonolaimus species; Pine nematodes, Bursaphelenchus xylophilus and other Bursaphelenchus species; Ring
  • the compounds of formula (I) and their salts are also useful for controlling arachnids (Arachnoidea), such as acarians (Acarina), e.g. of the families Argasidae, Ixodidae and Sarcoptidae, such as Amblyomma americanum, Amblyomma variegatum, Argas persicus, Boophilus annulatus, Boophilus decoloratus, Boophilus microplus, Dermacentor silvarum, Hyalomma truncatum, Ixodes ricinus, Ixodes rubicundus, Ornithodorus moubata, Otobius megnini, Dermanyssus gallinae, Psoroptes ovis, Rhipicephalus appendiculatus, Rhipicephalus evertsi, Sarcoptes scabiei, and Eriophyidae spp.
  • arachnoidea such as acarians
  • Tetranychidae spp. such as Tetranychus cinnabarinus, Tetranychus kanzawai, Tetranychus pacificus, Tetranychus telarius and Tetranychus urticae, Panonychus ulmi, Panonychus citri, and oligonychus pratensis.
  • the present invention provides the compounds of formula (I) which are useful for controlling insects selected form sucking or piercing insects such as insects from the genera Thysanoptera, Diptera and Hemiptera, in particular the following species: Thysanoptera: Frankliniella fusca, Frankliniella occidentalis, Frankliniella tritici, Scirtothrips citri, Thrips oryzae, Thrips palmi and Thrips tabaci, Diptera: Aedes aegypti, Aedes albopictus, Aedes vexans, Anastrepha ludens, Anopheles maculipennis, Anopheles crucians, Anopheles albimanus, Anopheles gambiae, Anopheles freeborni, Anopheles leucosphyrus, Anopheles minimus, Anopheles quadrimaculatus, Calliphora vicina, Ceratitis capitata, Chrysanoptera and Franklini
  • the present invention of the compound of formula (I) is useful for controlling diamondback moth (Plutella xylostella), american bollworm H ⁇ bner (Helicoveipa armigera), fall armyworm (Spodoptera frugiperdd), tobacco cutworm, cluster caterpillar Fabricius (Spodoptera litura), western flower thrips (Frankliniella occidentalis), potato leafhopper (Empoasca fabae), cotton melon aphid (Aphis gossypii), green peach aphid (Myzus persicae), brown planthopper Stal (Nilaparvata lugens), and sweetpotato whitefly (Bemisia tabaci).
  • the present invention provides a composition comprising a biologically effective amount of the compound of formula (I) and at least one additional biological active compatible compound selected from fungicides, insecticides, nematicides, acaricides, biopesticides, herbicides, plant growth regulators, antibiotics, fertilizers, nutrients and biostimulants.
  • the compounds used in the composition and in combination with the compound of formula (I) are also termed as active compatible compounds.
  • the known and reported fungicides, insecticides, nematicides, acaricides, biopesticides, herbicides, plant growth regulators, antibiotics and nutrients can be combined with at least one compound of the formula (I) of the present disclosure.
  • fungicides, insecticides, nematicides, acaricides, biopesticides, herbicides, plant growth regulators, antibiotics, fertilizers, nutrients disclosed and reported in WO2016156129 and/or WO2017153200 can be combined with at least one compound of formula (I) of the present disclosure.
  • the fungicides, insecticides, nematicides, acaricides, biopesticides, herbicides, plant growth regulators, antibiotics, fertilizers and nutrients reported in WO2016156129 and or WO2017153200 are incorporated herein by way of reference as non-limiting examples to be combined with at least one compound of the formula (I) of the present disclosure.
  • the compounds of the present invention can be mixed with at least one additional biological active compatible compound (mixing partner) which includes but is not limited to insecticides, fungicides, nematocides, bactericides, acaricides, growth regulators such as rooting stimulants, chemosterilants, semiochemicals, repellents, attractants, pheromones, feeding stimulants, other biologically active compounds or entomopathogenic bacteria, virus or fungi to form a multi-component pesticide giving an even broader spectrum of agricultural utility.
  • additional biological active compatible compound includes but is not limited to insecticides, fungicides, nematocides, bactericides, acaricides, growth regulators such as rooting stimulants, chemosterilants, semiochemicals, repellents, attractants, pheromones, feeding stimulants, other biologically active compounds or entomopathogenic bacteria, virus or fungi to form a multi-component pesticide giving an even broader spectrum of
  • the biological agents for mixing with compounds of the present invention include Bacillus thuringiensis, Bacillus thuringiensis delta endotoxin as well as naturally occurring and genetically modified viral insecticides including members of the family Baculoviridae as well as entomophagous fungi.
  • combinations with other invertebrate pest control compounds or agents, having a similar spectrum of control but a different mode of action will be particularly advantageous for resistance management.
  • compositions of the present invention can further comprise a biologically effective amount of at least one additional invertebrate pest control compound or agent having a similar spectrum of control but a different mode of action.
  • the biologically effective amount of the compound of formula (I) in the compositions ranges from 0.1 % to 99 % by weight with respect to the total weight of the composition, preferably from 5 % to 50 % by weight with respect to the total weight of the composition.
  • the present invention furthermore provides a method of combating invertebrate pests, said method comprising contacting the invertebrate pests, their habitat, breeding ground, food supply, plant, seed, soil, area, material or environment in which the invertebrate pests are growing or may grow, or the materials, plants, seeds, soils, surfaces or spaces to be protected from pest attack or infestation with a biologically effective amount of the compound of formula (I) or agriculturally acceptable salts, stereo-isomers, diastereomers, enantiomers, tautomers, metal complexes, polymorphs, or N-oxides thereof, composition or combination thereof.
  • Invertebrate pests are controlled and protection of agronomic, horticultural and specialty crops, animal and human health is achieved by applying one or more of the compounds of the present invention, in an effective amount, to the environment of the pests including the agronomic and/or nonagronomic locus of infestation, to the area to be protected, or directly on the pests to be controlled.
  • the present invention further comprises a method for the control of foliar- and soil-inhabiting invertebrates and protection of agronomic and/or nonagronomic crops, comprising contacting the invertebrates or their environment with a biologically effective amount of one or more of the compounds of the present invention, or with a composition comprising at least one such compound or a composition comprising at least one such compound and an effective amount of at least one additional biologically active compound or agent.
  • a preferred method of contact is by spraying.
  • a granular composition comprising a compound of the present invention can be applied to the plant foliage or the soil.
  • Compounds of the present invention are effective in delivery through plant uptake by contacting the plant with a composition comprising a compound of the present invention applied as a soil drench of a liquid formulation, a granular formulation to the soil, a nursery box treatment or a dip of transplants.
  • Other methods of contact include application of a compound or a composition of the present invention by direct and residual sprays, aerial sprays, seed coats, microencapsulations, systemic uptake, baits, eartags, boluses, foggers, fumigants, aerosols, dusts and many others.
  • the compounds of the present invention can be incorporated into baits that are consumed by the invertebrates or within devices such as traps and the like.
  • Granules or baits comprising between 0.01-5 % active ingredient, 0.05-10 % moisture retaining agent(s) and 40-99 % vegetable flour are effective in controlling soil insects at very low application rates, particularly at doses of active ingredient that are lethal by ingestion rather than by direct contact.
  • the compounds of the present invention can be applied in their pure state, but most often application will be of a formulation comprising one or more compounds with suitable carriers, diluents, and surfactants and possibly in combination with a food depending on the contemplated end use.
  • a preferred method of application involves spraying a water dispersion or refined oil solution of the compounds.
  • Combinations with spray oils, spray oil concentrations, spreader, stickers, adjuvants, other solvents, and synergists such as piperonyl butpxide often enhance compound efficacy.
  • the rate of application required for effective control i.e. "biologically effective amount" will depend on such factors as the species of invertebrate to be controlled, the pest′s life cycle, life stage, its size, location, time of year, host crop or animal, feeding behavior, mating behavior, ambient moisture, temperature, and the like. Under normal circumstances, application rates of about 0.01 to 2 kg of active ingredient per hectare are sufficient to control pests in agronomic ecosystems, but as little as 0.0001 kg/ hectare may be sufficient or as much as 8 kg/hectare may be required.
  • animal pest includes arthropods, gastropods, and nematodes.
  • Preferred animal pests according to the invention are arthropods, preferably insects and arachnids, in particular insects.
  • Insects, which are of particular relevance for crops, are typically referred to as crop insect pests.
  • the animal pest i.e.
  • the arthropods, gastropods, and nematodes, the plant, soil or water in which the plant is growing can be contacted with compounds of formula (I), their N-oxides and salts or composition(s) containing them by any application method known in the art.
  • contacting includes both direct contact (applying the compounds/compositions directly on the animal pest or plant typically to the foliage, stem or roots of the plant) and indirect contact (applying the compounds/compositions to the locus of the animal pest or plant).
  • the compounds of the present invention or the pesticidal compositions comprising them may be used to protect growing plants and crops from attack or infestation by animal pests, especially insects, acaridae or arachnids by contacting the plant/crop with a pesticidally effective amount of at least one compound of the present invention.
  • crop refers both to growing and harvested crops.
  • the compounds of the invention are also suitable for use in combating or controlling animal pests.
  • the invention also relates to a method of combating or controlling animal pests, which comprises contacting the animal pests, their habitat, breeding ground, or food supply, or the crops, plants, plant propagation materials, such as seeds, or soil, or the area, material or environment in which the animal pests are growing or may grow, with a pesticidally effective amount of a compound of the invention.
  • the present invention provides a method for protecting crops from an attack or infestation by invertebrate pests, which comprises contacting the crop with a biologically effective amount of the compound or the composition of the present invention, stereo-isomer, polymorph, N-oxide or salt thereof.
  • the compounds of the present invention are employed as such or in form of compositions by treating the insects or the plants, plant propagation materials, such as seeds, soil, surfaces, materials or rooms to be protected from insecticidal attack with an insecticidally effective amount of the active compounds.
  • the application can be carried out both before and after the infection of the plants, plant propagation materials, such as seeds, soil, surfaces, materials or rooms by the insects.
  • the present invention provides a method for the protection of seeds from soil insects and of the seedlings roots and shoots from soil and foliar insects comprising contacting the seeds before sowing and/or after pre-germination with the compound or the composition of the present invention, N- oxide or salt thereof.
  • the present invention provides a method for treating or protecting animals against infestation or infection by parasites which comprises orally, topically or parenterally administering or applying to the animals a biologically effective amount of compound or composition of the present invention, stereo- isomer, polymorph, N-oxide or veterinary acceptable salt thereof.
  • the rate of application (applying effective dosages) of the compound of the present invention may be in the range of 1g a.i .to 2000g a.i. per hectare in agricultural or horticultural crops, preferably from 10 g to 600 g per hectare, more preferably from 50 g to 500 g per hectare.
  • the compounds and the compositions of the present invention are particularly useful in the control of a multitude of insects on various cultivated plants, such as cereal, root crops, oil crops, vegetables, spices, ornamentals, for example seed of durum and other wheat, barley, oats, rye, maize (fodder maize and sugar maize / sweet and field corn), soybeans, oil crops, crucifers, cotton, sunflowers, bananas, rice, oilseed rape, turnip rape, sugarbeet, fodder beet, eggplants, potatoes, grass, lawn, turf, fodder grass, tomatoes, leeks, pumpkin/squash, cabbage, iceberg lettuce, pepper, cucumbers, melons, Brassica species, melons, beans, peas, garlic, onions, carrots, tuberous plants such as potatoes, sugar cane, tobacco, grapes, petunias, geranium/pelargoniums, pansies and impatiens.
  • the compound or the composition of the present invention are useful in protecting agricultural crops such as cereals, corn, sorghum, bajra, rice, soybean, oil seeds and other leguminous plants, fruits and fruit trees, grapes, nuts and nut trees, citrus and citrus trees, any horticultural plants, cucurbitaceae, oleaginous plants, tobacco, coffee, tea, cacao, sugar beet, sugar cane, cotton, potato, tomato, onions, peppers, other vegetables and ornamentals.
  • the compounds of the present invention are effective through both contact (via soil, glass, wall, bed net, carpet, plant parts or animal parts), and ingestion (bait or plant part).
  • the compounds of the present invention may also be applied against non-crop invertebrate pests, such as ants, termites, wasps, flies, mosquitos, crickets, or cockroaches.
  • non-crop insect pest refers to pests, which are particularly relevant for non-crop targets, such as ants, termites, wasps, flies, ticks, mosquitos, crickets, or cockroaches.
  • the bait can be a liquid, a solid or a semisolid preparation (e.g. a gel). Solid baits can be formed into various shapes and forms suitable to the respective application e.g.
  • Liquid baits can be filled into various devices to ensure proper application, e.g. open containers, spray devices, droplet sources, or evaporation sources.
  • Gels can be based on aqueous or oily matrices and can be formulated to particular necessities in terms of stickyness, moisture retention or aging characteristics.
  • the bait employed in the composition is a product, which is sufficiently attractive to incite insects such as ants, termites, wasps, flies, mosquitos, crickets etc. or cockroaches to eat it. The attractiveness can be manipulated by using feeding stimulants or sex pheromones.
  • Food stimulants are chosen, for example, but not exclusively, from animal and/or plant proteins (meat-, fish or blood meal, insect parts, egg yolk), from fats and oils of animal and/or plant origin, or mono-, oligo or polyorganosaccharides, especially from sucrose, lactose, fructose, dextrose, glucose, starch, pectin or even molasses or honey. Fresh or decaying parts of fruits, crops, plants, animals, insects or specific parts thereof can also serve as a feeding stimulant. Sex pheromones are known to be more insect specific. Specific pheromones are described in the literature and are known to those skilled in the art.
  • the typical content of active ingredient is from 0.001 weight % to 15 weight %, desirably from 0.001 weight % to 5 weight % of active compound.
  • Formulations of compounds of the present invention as aerosols are highly suitable for the non-professional user for controlling pests such as flies, fleas, ticks, mosquitos or cockroaches.
  • Aerosol recipes are preferably composed of the active compound, solvents such as lower alcohols (e.g. methanol, ethanol, propanol, butanol), ketones (e.g. acetone, methyl ethyl ketone), paraffin hydrocarbons (e.g.
  • kerosenes having boiling ranges of approximately 50 to 250 °C, dimethylformamide, N-methylpyrrolidone, dimethyl sulfoxide, aromatic hydrocarbons such as toluene, xylene, water, furthermore auxiliaries such as emulsifiers such as sorbitol monooleate, oleyl ethoxylate having 3-7 mol of ethylene oxide, fatty alcohol ethoxylate, perfume oils such as ethereal oils, esters of medium fatty acids with lower alcohols, aromatic carbonyl compounds, if appropriate stabilizers such as sodium benzoate, amphoteric surfactants, lower epoxides, triethyl orthoformate and, if required, propellants such as propane, butane, nitrogen, compressed air, dimethyl ether, carbon dioxide, nitrous oxide, or mixtures of these gases.
  • emulsifiers such as sorbitol monooleate, oleyl ethoxylate having 3-7 mol of
  • the oil spray formulations differ from the aerosol recipes in that no propellants are used.
  • the content of active ingredient is from 0.001 to 80 weights %, preferably from 0.01 to 50 weight % and most preferably from 0.01 to 15 weight %.
  • the compounds of the present invention and their respective compositions can also be used in mosquito and fumigating coils, smoke cartridges, vaporizer plates or long-term vaporizers and also in moth papers, moth pads or other heat-independent vaporizer systems.
  • the methods to control infectious diseases transmitted by insects e.g.
  • Insecticidal compositions for application to fibers, fabric, knitgoods, nonwovens, netting material or foils and tarpaulins preferably comprise a mixture including the insecticide, optionally a repellent and at least one binder.
  • Suitable repellents for example are ⁇ , ⁇ -diethyl- meta-toluamide (DEET), N,N-diethylphenylacetamide (DEPA), 1-(3-cyclohexan-1-yl-carbonyl)-2- methylpiperine, (2hydroxymethylcyclohexyl) acetic acid lactone, 2-ethyl-1 ,3-hexandiol, indalone, Methylneodecanamide (MNDA), a pyrethroid not used for insect control such as ⁇ (+/-)-3-allyl-2-methyl4- oxocyclopent-2-(+)-enyl-(+)-trans-chrysantemate (Esbiothrin), a repellent derived from or identical with plant extracts like limonene, eugenol, (+)-Eucamalol (1 ), (-)-1-epi-eucamalol or crude plant extracts from plants like Eucalyp
  • Suitable binders are selected for example from polymers and copolymers of vinyl esters of aliphatic acids (such as such as vinyl acetate and vinyl versatate), acrylic and methacrylic esters of alcohols, such as butyl acrylate, 2-ethylhexylacrylate, and methyl acrylate, mono- and di-ethylenically unsaturated hydrocarbons, such as styrene, and aliphatic diens, such as butadiene.
  • the impregnation of curtains and bednets is done in general by dipping the textile material into emulsions or dispersions of the insecticide or spraying them onto the nets.
  • the compounds of the present invention and their compositions can be used for protecting wooden materials such as trees, board fences, sleepers, etc. and buildings such as houses, outhouses, factories, but also construction materials, furniture, leathers, fibers, vinyl articles, electrie wires and cables etc. from ants and/or termites, and for controlling ants and termites from doing harm to crops or human being (e.g. when the pests invade into houses and public facilities).
  • the compounds of the present invention are applied not only to the surrounding soil surface or into the under-floor soil in order to protect wooden materials but it can also be applied to lumbered articles such as surfaces of the under-floor concrete, alcove posts, beams, plywoods, furniture, etc., wooden articles such as particle boards, half boards, etc.
  • a compound of the present invention is applied to the crops or the surrounding soil, or is directly applied to the nest of ants or the like.
  • a preferred method of application in the field of crop protection is application to the foliage of the plants (foliar application), it being possible to select frequency and rate of application to match the danger of infestation with the pest in question.
  • the active ingredient can reach the plants via the root system (systemic action), by drenching the locus of the plants with a liquid composition or by incorporating the active ingredient in solid form into the locus of the plants, for example into the soil, for example in the form of granules (soil application).
  • the active ingredient can reach the plants via the root system (systemic action), by drenching the locus of the plants with a liquid composition or by incorporating the active ingredient in solid form into the locus of the plants, for example into the soil, for example in the form of granules (soil application).
  • granules can be metered into the flooded paddy-field.
  • Digital Technologies The compounds of the invention can be used in combination with models e.g. embedded in computer programs for site specific crop management, satellite farming, precision farming or precision agriculture. Such models support the site specific management of agricultural sites with data from various sources such as soils, weather, crops (e.g. type, growth stage, plant health), weeds (e.g.
  • the compounds of the invention can be applied to a crop plant according to an appropriate dose regime if a model models the development of a pest and calculates that a threshold has been reached for which it is recommendable to apply the compound of the invention to the crop plant.
  • Commercially available systems which include agronomic models are e.g. FieldScriptsTM from The climate Corporation, XarvioTM from BASF, AGLogicTM from John Deere, etc.
  • the compounds of the invention can also be used in combination with smart spraying equipment such as e.g. spot spraying or precision spraying equipment attached to or housed within a farm vehicle such as a tractor, robot, helicopter, airplane, unmanned aerial vehicle (UAV) such as a drone, etc.
  • smart spraying equipment such as e.g. spot spraying or precision spraying equipment attached to or housed within a farm vehicle such as a tractor, robot, helicopter, airplane, unmanned aerial vehicle (UAV) such as a drone, etc.
  • Such an equipment usually includes input sensors (such as e.g. a camera) and a processing unit configured to analyze the input data and configured to provide a decision based on the analysis of the input data to apply the compound of the invention to the crop plants (respectively the weeds) in a specific and precise manner.
  • the use of such smart spraying equipment usually also requires positions systems (e.g.
  • the present invention further provides a seed comprising the compounds of the present invention, particularly in an amount ranging from about 0.0001% to about 1% by weight of the seed before treatment.
  • the compounds of the present invention are also suitable for the treatment of seeds in order to protect the seed from insect pest, in particular from soil-living insect and mite pests and the resulting plant′s roots and shoots against soil pests and foliar insects.
  • the compounds of the present invention are particularly useful for the protection of the seed from soil pests and the resulting plant′s roots (white grub, termites, wireworms) and shoots against soil pests and foliar insects.
  • the protection of the resulting plant′s roots and shoots is preferred. More preferred is the protection of resulting plant′s shoots from piercing and sucking insects, wherein the protection from aphids, jassids, thrips and white flies is most preferred.
  • the present invention therefore comprises a method for the protection of seeds from insects, in particular from soil insects and of the seedling roots and shoots from insects, in particular from soil and foliar insects, said method comprising contacting the seeds before sowing and/or after pregermination with a compound of the present invention thereof.
  • a method wherein the plant′s roots and shoots are protected, more preferably a method, wherein the plants shoots are protected form piercing and sucking insects, most preferably a method, wherein the plants shoots are protected from aphids.
  • seed embraces seeds and plant propagules of all kinds including but not limited to true seeds, seed pieces, suckers, corms, bulbs, fruit, tubers, grains, cuttings, cut shoots and the like and means in a preferred embodiment true seeds.
  • seed treatment comprises all suitable seed treatment techniques known in the art, such as seed dressing, seed coating, seed dusting, seed soaking and seed pelleting.
  • the present invention also comprises seeds coated with or containing the active compound. The seeds can be coated with seed coating compositions containing the compounds of the present invention.
  • seed coating compositions reported in EP3165092, EP3158864, WO2016198644, WO2016039623, WO2015192923, CA2940002, US2006150489, US2004237395, WO2011028115, EP2229808, WO2007067042, EP1795071, EP1273219, WO200178507, EP1247436, NL1012918 and CA2083415.
  • coated with and/or containing generally signifies that the active ingredient is for the most part on the surface of the propagation product at the time of application, although a greater or lesser part of the ingredient may penetrate into the propagation product, depending on the method of application. When the propagation product is (re)planted, it may absorb the active ingredient along with moisture.
  • Suitable seed is seeds of cereals, root crops, oil crops, vegetables, spices, ornamentals, for example seed of durum and other wheat, barley, oats, rye, maize (fodder maize and sugar maize/sweet and field corn), soybeans, oil crops, crucifers, cotton, sunflowers, bananas, rice, oilseed rape, turnip rape, sugarbeet, fodder beet, eggplants, potatoes, grass, lawn, turf, fodder grass, tomatoes, leeks, pumpkin/squash, cabbage, iceberg lettuce, pepper, cucumbers, melons, Brassica species, melons, beans, peas, garlic, onions, carrots, tuberous plants such as potatoes, sugar cane, tobacco, grapes, petunias, geranium/pelargoniums, pansies and impatiens.
  • the compounds of the present invention may be used for treating seeds from plants, which tolerate the action of herbicides or fungicides or insecticides owing to breeding, including genetic engineering methods.
  • the compounds of the present invention can be employed in treatment of seeds from plants, which are resistant to herbicides from the group consisting of the sulfonylureas, imidazolinones, glufosinate-ammonium or glyphosate-isopropylammonium and analogous active substances (see for example, EP242236, EP242246) (WO92/00377) (EP257993, US5013659) or in transgenic crop plants, for example cotton, with the capability of producing Bacillus thuringiensis toxins (Bt toxins) which make the plants resistant to certain pests (EP142924, EP193259).
  • Bt toxins Bacillus thuringiensis toxins
  • the compound of the present invention can be used for the treatment of seeds from plants, which have modified characteristics in comparison with existing plants, which can be generated for example by traditional breeding methods and/or the generation of mutants, or by recombinant procedures).
  • a number of cases have been described of recombinant modifications of crop plants for the purpose of modifying the starch synthesized in the plants (e.g. WO92/11376, WO92/14827, WO91/19806) or of transgenic crop plants having a modified fatty acid composition (WO91/13972).
  • the seed treatment application of the compound of the present invention is carried out by spraying or by dusting the seeds before sowing of the plants and before emergence of the plants.
  • compositions which are especially useful for seed treatment are e.g.: A. Soluble concentrates (SL, LS) B. Emulsions (EW, EO, ES) C. Suspensions (SC, OD, FS) D. Water-dispersible granules and water-soluble granules (WG, SG) E. Water-dispersible powders and water-soluble powders (WP, SP, WS) F. Gel-Formulations (GF) G.
  • Dustable powders Conventional seed treatment formulations include for example flowable concentrates FS, solutions LS, powders for dry treatment DS, water dispersible powders for slurry treatment WS, water-soluble powders SS and emulsion ES and EC and gel formulation GF. These formulations can be applied to the seed diluted or undiluted. Application to the seeds is carried out before sowing, either directly on the seeds or after having pregerminated the latter. In one embodiment a FS formulation is used for seed treatment.
  • a FS formulation may comprise 1-800 g/l of active ingredient, 1-200 g/l surfactant, 0 to 200 g/l antifreezing agent, 0 to 400 g/l of binder, 0 to 200 g/l of a pigment and up to 1 liter of a solvent, preferably water.
  • Especially FS formulations of compounds of the present invention for seed treatment usually comprise from 0.1 to 80% by weight (1 to 800 g/l) of the active ingredient, from 0.1 to 20 % by weight (1 to 200 g/l) of at least one surfactant, e.g.0.05 to 5 % by weight of a wetter and from 0.5 to 15 % by weight of a dispersing agent, up to 20 % by weight, e.g.
  • an anti-freeze agent from 5 to 20 % of an anti-freeze agent, from 0 to 15 % by weight, e.g.1 to 15 % by weight of a pigment and/or a dye, from 0 to 40 % by weight, e.g.1 to 40 % by weight of a binder (sticker /adhesion agent), optionally up to 5 % by weight, e.g. from 0.1 to 5 % by weight of a thickener, optionally from 0.1 to 2 % of an anti-foam agent, and optionally a preservative such as a biocide, antioxidant or the like, e.g. in an amount from 0.01 to 1 % by weight and a filler/vehicle up to 100 % by weight.
  • a binder sticker /adhesion agent
  • a preservative such as a biocide, antioxidant or the like, e.g. in an amount from 0.01 to 1 % by weight and a filler/
  • Seed treatment formulations may additionally comprise binders and optionally colorants. Binders can be added to improve the adhesion of the active materials on the seeds after treatment. Suitable binders are homo and copolymers from alkylene oxides like ethylene oxide or propylene oxide, polyvinylacetate, polyvinylalcohols, polyvinylpyrrolidones, and copolymers thereof, ethylene-vinyl acetate copolymers, acrylic homo and copolymers, polyethyleneamines, polyethyleneamides and polyethylenepyrimidines, polysaccharides like celluloses, tylose and starch, polyolefin homo and copolymers like olefin/maleic anhydride copolymers, polyurethanes, polyesters, polystyrene homo and copolymers.
  • alkylene oxides like ethylene oxide or propylene oxide
  • polyvinylacetate polyvinylalcohols
  • polyvinylpyrrolidones and copolymers
  • colorants can be included in the formulation. Suitable colorants or dyes for seed treatment formulations are Rhodamin B, C.I. Pigment Red 112, C.I. Solvent Red 1 , pigment blue 15:4, pigment blue 15:3, pigment blue 15:2, pigment blue 15:1 , pigment blue 80, pigment yellow 1 , pigment yellow 13, pigment red 112, pigment red 48:2, pigment red 48:1 , pigment red 57:1 , pigment red 53:1 , pigment orange 43, pigment orange 34, pigment orange 5, pigment green 36, pigment green 7, pigment white 6, pigment brown 25, basic violet 10, basic violet 49, acid red 51 , acid red 52, acid red 14, acid blue 9, acid yellow 23, basic red 10, basic red 108.
  • the application rates of the compounds of the present invention are generally from 0.1 g to 5 kg per 100 kg of seed, preferably from 1 g to 1 kg per 100 kg of seed, more preferably from 1 g to 200 g per 100 kg of seed and in particular from 5 g to 150 g per 100 kg of seeds and 10 g to 100g per 100 kg of seed.
  • the present invention therefore also provides to seeds comprising a compound of formula (I), or an agriculturally useful salt of the compound of formula (I), as defined herein.
  • the amount of the compound of formula (I) or the agriculturally useful salt thereof will in general vary from 0.1 g to 5 kg per 100 kg of seed, preferably from 1 g to 1 kg per 100 kg of seed, more preferably from 1 g to 200 g per 100 kg of seed and in particular from 5 g to 150 g per 100 kg of seeds and 10 g to 100 g per 100 kg of seeds.
  • Animal health also provides an agricultural and/or veterinary composition comprising at least one compound of formula (I).
  • the present invention provides the use of the compound of formula (I), agriculturally acceptable salts, stereo-isomers, diastereomers, enantiomers, tautomers, metal complexes, polymorphs, or N-oxides, composition or combination thereof, for combating invertebrate pests in agricultural crops and/or horticultural crops or parasites on animals.
  • the compounds of formula (I), their N-oxides and/or veterinarily acceptable salts thereof are in particular also suitable for being used for combating parasites in and on animals.
  • the present invention also provides a compositions containing a parasiticidally effective amount of at least one compound of formula (I), N-oxide or veterinarily acceptable salt thereof and an acceptable carrier, for combating parasites in and on animals.
  • the present invention also provides a method for treating, controlling, preventing and protecting animals against infestation and infection by parasites, which comprises orally, topically, or parenteral administering or applying to the animals a parasiticidally effective amount of a compound of the present invention or a composition comprising it.
  • the present invention also provides a process for the preparation of a composition for treating, controlling, preventing or protecting animals against infestation or infection by parasites which comprises a parasiticidally effective amount of a compound of the present invention or a composition comprising it.
  • mammals such as cattle, sheep, swine, camels, deer, horses, pigs, poultry, rabbits, goats, dogs and cats, water buffalo, donkeys, fallow deer and reindeer, and also in fur-bearing animals such as mink, chinchilla and raccoon, birds such as hens, geese, turkeys and ducks and fish such as freshand salt-water fish as trout, carp and eels.
  • Compounds of the present invention and compositions comprising them are preferably used for controlling and preventing infestations and infections in domestic animals, such as dogs or cats.
  • Infestations in warm-blooded animals and fish include, but are not limited to, lice, biting lice, ticks, nasal bots, keds, biting flies, muscoid flies, flies, myiasitic fly larvae, chiggers, gnats, mosquitoes and fleas.
  • the compounds of the present invention and compositions comprising them are suitable for systemic and/or non-systemic control of ecto and/or endoparasites. They can be active against all or some stages of development.
  • the compounds of the present invention are especially useful for combating ectoparasites.
  • the compounds of the present invention are especially useful for combating parasites of the following orders and species, respectively: fleas (Siphonaptera), e.g. Ctenocephalides felis, Ctenocephalides cams, Xenopsylla cheopis, Pulex irritans, Tunga penetrans, and Nosopsyllus fasciatus, cockroaches (Blattaria Blattodea), e.g.
  • Blattella germanica Blattella asahinae, Periplaneta americana, Periplaneta japonica, Periplaneta brunnea, Periplaneta fuligginosa, Periplaneta australasiae, and Blatta orientalis, flies, mosquitoes (Diptera), e.g.
  • Pediculus humanus capitis Pediculus humanus corporis, Pthirus pubis, Haematopinus eurysternus, Haematopinus suis, Linognathus vituli, Bovicola bovis, Menopon gallinae, Menacanthus stramineus and Solenopotes capillatus. ticks and parasitic mites (Parasitiformes): ticks (Ixodida), e.g.
  • Anoplurida e.g. Haematopinus spp., Linognathus spp., Pediculus spp., Phtirus spp., and Solenopotes spp, Mallophagida (suborders Arnblycerina and Ischnocerina), e.g. Trimenopon spp., Menopon spp., Trinoton spp., Bovicola spp., Werneckiella spp., Lepikentron spp., Trichodectes spp., and Felicola spp.
  • Anoplurida e.g. Haematopinus spp., Linognathus spp., Pediculus spp., Phtirus spp., and Solenopotes spp, Mallophagida (suborders Arnblycerina and Ischnocerina), e.g. Trimenopon spp
  • Roundworms Nematoda Wipeworms and Trichinosis (Trichosyringida), e.g. Trichinellidae (Trichinella spp.), (Trichuridae,) Trichuris spp., Capillaria spp, Rhabditida, e.g. Rhabditis spp, Strongyloides spp., Helicephalobus spp, Strongylida, e.g. Strongylus spp., Ancylostoma spp., Necator americanus, Bunostomum spp.
  • Trichostrongylus spp. Haemonchus contortus., Ostertagia spp., Cooperia spp., Nematodirus spp., Dictyocaulus spp., Cyathostoma spp., Oesophagostomum spp., Stephanurus dentatus, Ollulanus spp., Chabertia spp., Stephanurus dentatus , Syngamus trachea, Ancylostoma spp., Uncinaria spp., Globocephalus spp., Necator spp., Metastrongylus spp., Muellerius capillaris, Protostrongylus spp., Angiostrongylus spp., Parelaphostrongylus spp.
  • Faciola spp. Fascioloides magna, Paragonimus spp., Dicrocoelium spp., Fasciolopsis buski, Clonorchis sinensis, Schistosoma spp., Trichobilharzia spp., Alaria a lata, Paragonimus spp., and Nanocyetes spp, Cercomeromorpha, in particular Cestoda (Tapeworms), e.g.
  • Diphyllobothrium spp. Diphyllobothrium spp., Tenia spp., Echinococcus spp., Dipylidium caninum, Multiceps spp., Hymenolepis spp., Mesocestoides spp., Vampirolepis spp., Moniezia spp., Anoplocephala spp., Sirometra spp., Anoplocephala spp., and Hymenolepis spp.
  • the compounds of formula (I) and compositions containing them are particularly useful for the control of pests from the orders Diptera, Siphonaptera and Ixodida.
  • the present invention provides use of the compounds of formula (I) and compositions containing them for combating mosquitoes. In one embodiment, the present invention provides use of the compounds of formula (I) and compositions containing them for combating flies. In one embodiment, the present invention provides use of the compounds of formula (I) and compositions containing them for combating fleas. The use of the compounds of the present invention and compositions containing them for combating ticks is still another embodiment of the present invention. The compounds of the present invention are also especially useful for combating endoparasites (roundworms nematoda, thorny headed worms and planarians). In one embodiment, the administration of the compounds of the present invention can be carried out both prophylactically and therapeutically.
  • administration of the compounds of the present invention is carried out directly or in the form of suitable preparations, orally, topically/dermally or parenterally.
  • compounds of the present invention may be formulated as animal feeds, animal feed premixes, animal feed concentrates, pills, solutions, pastes, suspensions, drenches, gels, tablets, boluses and capsules.
  • the compounds of the present invention may be administered to the animals in their drinking water.
  • the dosage form chosen should provide the animal with 0.01 mg/kg to 100 mg/kg of animal body weight per day of the compound of the present invention, preferably with 0.5 mg/kg to 100 mg/kg of animal body weight per day.
  • the compounds of the present invention may be administered to animals parenterally, for example, by intraruminal, intramuscular, intravenous or subcutaneous injection.
  • the compounds of the present invention may be dispersed or dissolved in a physiologically acceptable carrier for subcutaneous injection.
  • the compounds of the present invention may be formulated into an implant for subcutaneous administration.
  • the compound of the present invention may be transdermally administered to animals.
  • the dosage form chosen should provide the animal with 0.01 mg/kg to 100 mg/kg of animal body weight per day of the compound of the present invention.
  • the compounds of the present invention may also be applied topically to the animals in the form of dips, dusts, powders, collars, medallions, sprays, shampoos, spot-on and pour-on formulations and in ointments or oil-in-water or water-in-oil emulsions.
  • dips and sprays usually contain 0.5 ppm to 5,000 ppm and preferably 1 ppm to 3,000 ppm of the compound of the present invention.
  • the compounds of the present invention may be formulated as ear tags for animals, particularly quadrupeds such as cattle and sheep.
  • Suitable preparations are: Solutions such as oral solutions, concentrates for oral administration after dilution, solutions for use on the skin or in body cavities, pouring-on formulations, gels; Emulsions and suspensions for oral or dermal administration; semi-solid preparations; Formulations in which the active compound is processed in an ointment base or in an oil-in-water or water-in-oil emulsion base; Solid preparations such as powders, premixes or concentrates, granules, pellets, tablets, boluses, capsules; aerosols and inhalants, and active compound-containing shaped articles.
  • compositions suitable for injection are prepared by dissolving the active ingredient in a suitable solvent and optionally adding further ingredients such as acids, bases, buffer salts, preservatives, and solubilizers.
  • suitable solvents are physiologically tolerable solvents such as water, alkanols such as ethanol, butanol, benzyl alcohol, glycerol, propylene glycol, polyethylene glycols, N-methylpyrrolidone, 2-pyrrolidone, and mixtures thereof.
  • the active compounds can optionally be dissolved in physiologically tolerable vegetable or synthetic oils which are suitable for injection.
  • Suitable solubilizers are solvents which promote the dissolution of the active compound in the main solvent or prevent its precipitation.
  • Examples are polyvinylpyrrolidone, polyvinyl alcohol, polyoxyethylated castor oil, and polyoxyethylated sorbitan ester. Suitable preservatives are benzyl alcohol, trichlorobutanol, p-hydroxybenzoic acid esters, and n-butanol.
  • Oral solutions are administered directly. Concentrates are administered orally after prior dilution to the used concentration. Oral solutions and concentrates are prepared according to the state of the art and as described above for injection solutions, sterile procedures not being necessary. Solutions for use on the skin are trickled on, spread on, rubbed in, sprinkled on or sprayed on.
  • Solutions for use on the skin are prepared according to the state of the art and according to what is described above for injection solutions, sterile procedures not being necessary.
  • Further suitable solvents are polypropylene glycol, phenyl ethanol, phenoxy ethanol, ester such as ethyl or butyl acetate, benzyl benzoate, ethers such as alkyleneglycol alkylether, e.g. dipropylenglycol monomethylether, ketons such as acetone, methylethylketone, aromatic hydrocarbons, vegetable and synthetic oils, dimethylformamide, dimethylacetamide, transcutol, solketal, propylencarbonate, and mixtures thereof. Gels are applied to or spread on the skin or introduced into body cavities.
  • Gels are prepared by treating solutions which have been prepared as described in the case of the injection solutions with sufficient thickener that a clear material having an ointment-like consistency results.
  • the thickeners employed are the thickeners given above.
  • Pour-on formulations are poured or sprayed onto limited areas of the skin, the active compound penetrating the skin and acting systemically.
  • Pour-on formulations are prepared by dissolving, suspending or emulsifying the active compound in suitable skin-compatible solvents or solvent mixtures. If appropriate, other auxiliaries such as colorants, bioabsorption-promoting substances, antioxidants, light stabilizers and adhesives are added.
  • Suitable solvents are for example, water, alkanols, glycols, polyethylene glycols, polypropylene glycols, glycerol, aromatic alcohols such as benzyl alcohol, phenylethanol, phenoxyethanol, esters such as ethyl acetate, butyl acetate, benzyl benzoate, ethers such as alkylene glycol alkyl ethers such as dipropylene glycol monomethyl ether, diethylene glycol mono-butyl ether, ketones such as acetone, methyl ethyl ketone, cyclic carbonates such as propylene carbonate, ethylene carbonate, aromatic and/or aliphatic hydrocarbons, vegetable or synthetic oils, dimethylformamide, dimethylacetamide, n-alkylpyrrolidones such as methylpyrrolidone, n-butylpyrrolidone or noctylpyrrolidone, N-methylpyrrolidone, 2-pyrroli
  • Suitable colorants are for example, all colorants permitted for the use on animals and which can be dissolved or suspended.
  • Suitable absorption-promoting substances are for example, dimethyl sulfoxide, spreading oils such as isopropyl myristate, dipropylene glycol pelargonate, silicone oils and copolymers thereof with polyethers, fatty acid esters, triglycerides or fatty alcohols.
  • Suitable antioxidants are for example, sulfites or metabisulfites such as potassium metabisulfite, ascorbic acid, butylhydroxytoluene, butylhydroxyanisole or tocopherol.
  • Suitable light stabilizers are for example, novantisolic acid.
  • Suitable adhesives are, for example, cellulose derivatives, starch derivatives, polyacrylates or natural polymers such as alginates, gelatin.
  • Emulsions can be administered orally, dermally or as injections.
  • Emulsions are either of the water-in-oil type or of the oil- in-water type. They are prepared by dissolving the active compound either in the hydrophobic or in the hydrophilic phase and homogenizing this with the solvent of the other phase with the aid of suitable emulsifiers and, if appropriate, other auxiliaries such as colorants, absorption-promoting substances, preservatives, antioxidants, light stabilizers, viscosity-enhancing substances.
  • Suitable hydrophobic phases are: Liquid paraffins, silicone oils, natural vegetable oils such as sesame oil, almond oil, castor oil, synthetic triglycerides such as caprylic/capric biglyceride, triglyceride mixture with vegetable fatty acids of the chain length C 1 -C 12 or other specially selected natural fatty acids, partial glyceride mixtures of saturated or unsaturated fatty acids possibly also containing hydroxyl groups, monoand diglycerides of the Cs-do fatty acids, fatty acid esters such as ethyl stearate, di-n-butyryl adipate, hexyl laurate, dipropylene glycol perlargonate, esters of a branched fatty acid of medium chain length with saturated fatty alcohols of chain length C 16 -C 18 , isopropyl myristate, isopropyl palmitate, caprylic/capric acid esters of saturated fatty alcohols of chain length C 12 -
  • Suitable hydrophilic phases are: water, alcohols such as propylene glycol, glycerol, sorbitol and mixtures thereof.
  • Suitable emulsifiers are for example, non-ionic surfactants, e.g. polyethoxylated castor oil, polyethoxylated sorbitan monooleate, sorbitan monostearate, glycerol monostearate, polyoxyethyl stearate, alkylphenol polyglycol ether; ampholytic surfactants such as di-sodium N-lauryl-p-iminodipropionate or lecithin.
  • Suitable anionic surfactants are for example, sodium lauryl sulfate, fatty alcohol ether sulfates, mono/dialkyl polyglycol ether orthophosphoric acid ester monoethanolamine salt; suitable cation-active surfactants are cetyltrimethylammonium chloride.
  • Suitable further auxiliaries are for example, substances which enhance the viscosity and stabilize the emulsion, such as carboxymethylcellulose, methylcellulose and other cellulose and starch derivatives, polyacrylates, alginates, gelatin, gum arabic, polyvinylpyrrolidone, polyvinyl alcohol, copolymers of methyl vinyl ether and maleic anhydride, polyethylene glycols, waxes, colloidal silicic acid or mixtures of the substances mentioned.
  • Suspensions can be administered orally or topically/dermally. They are prepared by suspending the active compound in a suspending agent, if appropriate with addition of other auxiliaries such as wetting agents, colorants, bioabsorption-promoting substances, preservatives, antioxidants, light stabilizers.
  • Liquid suspending agents are all homogeneous solvents and solvent mixtures. Suitable wetting agents (dispersants) are the emulsifiers given above. Other auxiliaries which may be mentioned are those given above. Semi-solid preparations can be administered orally or topically/dermally. They differ from the suspensions and emulsions described above only by their higher viscosity.
  • the active compound is mixed with suitable excipients, if appropriate with addition of auxiliaries, and brought into the desired form.
  • suitable excipients are all physiologically tolerable solid inert substances. Those used are inorganic and organic substances.
  • Inorganic substances are, for example, sodium chloride, carbonates such as calcium carbonate, hydrogencarbonates, aluminium oxides, titanium oxide, silicic acids, argillaceous earths, precipitated or colloidal silica, or phosphates.
  • Organic substances are, for example, sugar, cellulose, foodstuffs and feeds such as milk powder, animal meal, grain meals and shreds, starches. Suitable auxiliaries are preservatives, antioxidants, and/or colorants which have been mentioned above.
  • auxiliaries are lubricants and glidants such as magnesium stearate, stearic acid, talc, bentonites, disintegration-promoting substances such as starch or crosslinked polyvinylpyrrolidone, binders such as starch, gelatin or linear polyvinylpyrrolidone, and dry binders such as microcrystalline cellulose.
  • "parasiticidally effective amount” means the amount of active ingredient needed to achieve an observable effect on growth, including the effects of death, retardation of development, prevention, and removal, destruction, or otherwise diminishing the occurrence and activity of the target organism.
  • the parasiticidally effective amount can vary for the various compounds/compositions used in the present invention.
  • a parasiticidally effective amount of the compositions will also vary according to the prevailing conditions such as desired parasiticidal effect and duration, target species, mode of application, and the like.
  • the compositions which can be used in the present invention generally comprise from about 0.001 to 95% of the compound of the present invention. Generally, it is favorable to apply the compounds of the present invention in total amounts of 0.5 mg/kg to 100 mg/kg per day, preferably 1 mg/kg to 50 mg/kg per day.
  • Ready-to-use preparations contain the compounds acting against parasites, preferably ectoparasites, in concentrations of 10 ppm to 80 per cent by weight, preferably from 0.1 to 65 per cent by weight, more preferably from 1 to 50 per cent by weight, most preferably from 5 to 40 per cent by weight.
  • Preparations diluted before use contain the compounds acting against ectoparasites in concentrations of 0.5 to 90 per cent by weight, preferably of 1 to 50 per cent by weight.
  • the preparations comprise the compounds of the present invention against endoparasites in concentrations of 10 ppm to 2 per cent by weight, preferably of 0.05 to 0.9 per cent by weight, very particularly preferably of 0.005 to 0.25 per cent by weight.
  • compositions comprising the compounds of the present invention are applied dermally/topically.
  • topical application is conducted in the form of compound-containing shaped articles such as collars, medallions, ear tags, bands for fixing at body parts, and adhesive strips and foils.
  • solid formulations which release compounds of the present invention in total amounts of 10 mg/kg to 300 mg/kg, preferably 20 mg/kg to 200 mg/kg, most preferably 25 mg/kg to 160 mg/kg body weight of the treated animal in the course of three weeks.
  • thermoplastic and flexible plastics as well as elastomers and thermoplastic elastomers are used.
  • Suitable plastics and elastomers are polyvinyl resins, polyurethane, polyacrylate, epoxy resins, cellulose, cellulose derivatives, polyamides and polyester which are sufficiently compatible with the compounds of the present invention.
  • a detailed list of plastics and elastomers as well as preparation procedures for the shaped articles is given e.g. in WO 2003086075.
  • Positive crop response The compounds of the present invention not only control insect and mite pests effectively but also induce a positive crop response such as plant growth enhancement effects like enhanced root growth, enhanced tolerance to drought, high salt, high temperature, chill, frost or light radiation, improved flowering, enhanced nutrient utilization (such as improved nitrogen assimilation), enhanced quality of plant products, higher number of productive tillers, enhanced resistance to fungi, insects, pests and the like, which results in higher yields.
  • plant growth enhancement effects like enhanced root growth, enhanced tolerance to drought, high salt, high temperature, chill, frost or light radiation, improved flowering, enhanced nutrient utilization (such as improved nitrogen assimilation), enhanced quality of plant products, higher number of productive tillers, enhanced resistance to fungi, insects, pests and the like, which results in higher yields.
  • Step-2 Synthesis of tert-butyl 6-hydrazinylnicotinate
  • tert-butyl 6-chloronicotinate 10 g, 46.8 mmol
  • t-butanol 100 mL
  • hydrazine hydrate 23.91 mL, 468 mmol
  • the resulting reaction mixture was stirred at 85 °C for 5h.
  • the reaction mixture was concentrated under reduced pressure to obtain a sticky crude compound which was diluted with methyl tert-butyl ether (100 mL) and washed with water (50 mL) and brine solution (50 mL).
  • Step-1 Synthesis of (S)-6-(5-(1-(3-chloro-5-(trifluoromethyl) benzamido) ethyl)-3-methyl-1H-1,2,4-triazol-1- yl)-N-(dimethyl(oxo)- ⁇ 6 -sulfanylidene) nicotinamide
  • Step-1 Synthesis of (S)-N-(1-amino-1-oxopropan-2-yl)-3-chloro-5-(trifluoromethyl) benzamide
  • 3-chloro-5-(trifluoromethyl) benzoic acid (1 g, 4.45 mmol) in N,N- dimethylformamide (20 mL
  • N,N-diisopropylethylamine (2.33 mL, 13.4 mmol) was added, followed by the addition of 1-[Bis(dimethylamino)methylene]-1H-1,2,3-triazolo[
  • Step-2 Synthesis of tert-butyl (S)-6-(5-(1-(3-chloro-5-(trifluoromethyl) benzamido) ethyl)-3-methyl- 1H-1,2,4-triazol-1-yl) nicotinate
  • (S)-N-(1-amino-1-oxopropan-2-yl)-3-chloro-5-(trifluoromethyl) benzamide (2 g, 6.79 mmol) in dichloromethane (30 mL), 1,1-dimethoxy-N, N-dimethylethan-1-amine (1.60 mL, 10.8 mmol) was added, and the resulting mixture was stirred under reflux for 1 h.
  • reaction mixture was cooled to 25 °C and concentrated to get a crude compound which was dissolved in a mixture of 1,4-dioxane (20 mL), acetic acid (10 mL), followed by the addition of tert-butyl-6- hydrazenyl-nicotinate (1.63 g, 7.81 mmol) at 25 °C.
  • the resulting reaction mixture was stirred at 100 °C for 2 h.
  • the reaction mixture was concentrated under reduced pressure to get a crude sticky compound, which was dissolved in ethyl acetate (150 mL) and washed subsequently by water (50 mL) and brine (50 mL).
  • Step-3 Synthesis of (S)-6-(5-(1-(3-chloro-5-(trifluoromethyl) benzamido) ethyl)-3-methyl-1H-1,2,4- triazol-1-yl) nicotinic acid
  • tert-butyl (S)-6-(5-(1-(3-chloro-5-(trifluoromethyl) benzamido) ethyl)-3-methyl- 1H-1,2,4-triazol-1-yl) nicotinate 2.6 g, 5.10 mmol
  • dichloromethane 20 mL
  • trifluoroacetic acid 7.86 mL, 102 mmol
  • reaction mixture was stirred for 5-10 min, followed by the addition of iminodimethyl- ⁇ 6 - sulfanone (61.6 mg, 0.7 mmol) at 25 °C.
  • iminodimethyl- ⁇ 6 - sulfanone 61.6 mg, 0.7 mmol
  • the resulting reaction mixture was stirred at the same temperature for 2-3 h.
  • the reaction mixture was diluted with ethyl acetate (50 mL) and washed with water (3x30 mL) followed by brine (2x30 mL).
  • reaction mixture was dissolved in a mixture of 1,4-dioxane (50 mL) and acetic acid (50 mL), followed by the addition of 2-hydrazineyl-5-iodopyridine (3.33 g, 14.2 mmol). The reaction mixture was then stirred at 90 °C for 4 h. After the completion of the reaction, the reaction mixture was diluted with ethyl acetate (100 mL), quenched by the addition of saturated sodium bicarbonate (NaHCO 3, 100 mL) solution and washed with brine (50 mL).
  • NaHCO 3 saturated sodium bicarbonate
  • Step 3 Synthesis of (S)-1-(1-(5-iodopyridin-2-yl)-1H-1,2,4-triazol-5-yl) ethan-1-amine 2,2,2- trifluoroacetate
  • tert-butyl (S)-(1-(1-(5-iodopyridin-2-yl)-1H-1,2,4-triazol-5-yl) ethyl) carbamate (6.14 g, 14.8 mmol) in dichloromethane (100 mL)
  • trifluoroacetic acid 8.1 ml, 105 mmol
  • Step 4 Synthesis of (S)-N-(1-(1-(5-iodopyridin-2-yl)-1H-1,2,4-triazol-5-yl) ethyl)-3,5- bis(trifluoromethyl) benzamide
  • 3,5-bis(trifluoromethyl)benzoic acid 2.346 g, 9.09 mmol
  • N,N- dimethylformamide 40 mL
  • 1-[bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3- oxid hexafluorophosphate (3.46 g, 9.1 mmol) was added at 25 °C, and the resulting reaction mixture was stirred for 15 min, after which N,N-diisopropylethylamine (4.10 mL, 23.5 mmol) and (S)-1-(1-(5- iodopyridin-2-yl)-1H-1,
  • the resuting mixture was stirred for 24 h at 120 °C. After the completion of the reaction, the heterogeneous reaction mixture was cooled to 25 °C and diluted with ethyl acetate (25 mL). The resulting reaction mixture was filtered through a pad of celite and washed with a saturated sodium bicarbonate solution (10 mL).
  • Step 3 Synthesis of ethyl 3-((1-oxidotetrahydro- ⁇ 6 -thiophen-1-ylidene) amino)-5- (trifluoromethyl)benzoate
  • a 10 ml vial equipped with a magnetic stirring bar was charged with palladium (II) acetate (28.3 mg, 0.1 mmol) and xantphos (170 mg, 0.3 mmol) under an inert atmosphere.
  • reaction mixture was allowed to cool to 25 °C, diluted with ethyl acetate (20 mL), filtered through a pad of celite, and the obtained solid material was rinsed with ethyl acetate (10 mL).
  • the filtrate was concentrated under reduced pressure to obtain a crude product which was purified by column chromatography to obtain ethyl 3-((1-oxidotetrahydro- ⁇ 6 -thiophen- 1-ylidene) amino)-5-(trifluoromethyl) benzoate (230 mg, 0.7 mmol, 82 % yield).
  • reaction mixture was concentrated under reduced pressure and then acidified with 5% aqueous hydrochloride solution.
  • aqueous layer was extracted with ethyl acetate (80 mL x 2).
  • the combined organic layers were dried over anhydrous sodium sulphate (Na2SO4) and then concentrated under reduced pressure to obtain 3-((1-oxidotetrahydro- ⁇ 6 -thiophen-1- ylidene) amino)-5-(trifluoromethyl) benzoic acid (4.0 g, 13.0 mmol, 93 % yield) as a solid.
  • Step-2 Synthesis of tert-butyl (S)-(4-(5-bromopyridin-2-yl)-3,4-dioxobutan-2-yl)carbamate
  • tert-butyl ((2S)-4-(5-bromopyridin-2-yl)-3-hydroxy-4-oxobutan-2-yl)carbamate (10.5 g, 29.2 mmol) in dichloromethane (50 mL) and tetrahydrofuran (50 mL)
  • dess-Martinperiodinane (18.60 g, 43.8 mmol) was added portion wise at 0 °C, and the resulting mixture was stirred at 25 °C for 2 h.
  • reaction mixture was quenched cautiously with a saturated sodium bicaronate solution (100 mL) and the aqueous layer was extracted with ethyl acetate (200 mL x 2). The combined organic layers were washed with brine solution (100 mL x 2), dried over anhydrous sodium sulphate, filtered and concentrated under reduced pressure to obtain tert-butyl (S)-(4-(5-bromopyridin-2- yl)-3,4-dioxobutan-2-yl)carbamate (10 g, 28.0 mmol, 96 % yield) as yellow gum.
  • Step-3 Synthesis of tert-butyl (S)-(1-(3-(5-bromopyridin-2-yl)pyrazin-2-yl)ethyl)carbamate
  • tert-butyl (S)-(4-(5-bromopyridin-2-yl)-3,4-dioxobutan-2-yl)carbamate 11 g, 30.8 mmol
  • ethane-1,2-diamine 7.20 mL, 108 mmol
  • Step-4 Synthesis of tert-butyl (S)-(1-(3-(5-((dimethyl(oxo)- ⁇ 6 -sulfaneylidene)amino)pyridin-2- yl)pyrazin-2-yl)ethyl)carbamate
  • tert-butyl (S)-(1-(3-(5-bromopyridin-2-yl)pyrazin-2-yl)ethyl)carbamate 2.9 g, 7.65 mmol
  • iminodimethyl- ⁇ 6 -sulfanone 1.068 g, 11.47 mmol
  • potassium phosphate tribasic 3.25 g, 15.29 mmol
  • the resulting reaction mixture was degassed with nitrogen for 10 min followed by the addition of Pd2(dba) 3 (1.050 g, 1.147 mmol) and xantphos (1.549 g, 2.68 mmol). The resulting reaction mixture was stirred at 105 °C for 16 h.
  • reaction mixture was filterd through a celite bed, the celite bed was washed with ethyl acetate (200 mL x 2) and the filtrate was concentrated to get a crude sticky compound which was purified by column chromatography to obtain tert-butyl (S)-(1-(3-(5-((dimethyl(oxo)- ⁇ 6 - sulfaneylidene)amino)pyridin-2-yl)pyrazin-2-yl)ethyl)carbamate (2.7 g, 6.90 mmol, 90 % yield).
  • Step-5 Synthesis of (S)-((6-(3-(1-aminoethyl)pyrazin-2-yl)pyridin-3-yl)imino)dimethyl- ⁇ 6 -sulfanone tris(2,2,2-trifluoroacetate)
  • tert-butyl (S)-(1-(3-(5-((dimethyl(oxo)- ⁇ 6 -sulfaneylidene)amino)pyridin-2- yl)pyrazin-2-yl)ethyl)carbamate (3 g, 7.66 mmol) in dichloromethane (10 mL), trifluoroacetic acid (5.90 mL, 77 mmol) was added slowly, and the resulting reaction mixture was stirred at 25 °C for 16 h.
  • Step-6 Synthesis of (S)-N-(1-(3-(5-((dimethyl(oxo)- ⁇ 6 -sulfaneylidene)amino)pyridin-2-yl)pyrazin-2- yl)ethyl)-3,5-bis(trifluoromethyl)benzamide (103)
  • 3,5-bis(trifluoromethyl)benzoic acid (194 mg, 0.751 mmol) in N,N- dimethylformamide (3 mL)
  • 1-[bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxid hexafluorophosphate (285 mg, 0.751 mmol) and N,N-diisopropylethylamine (0.30 ml, 1.733 mmol) were added, and the resulting mixture was stirred at 25 °C for 10-15 min followed by the addition of (S)-((6-(3- (1
  • Step 2 Synthesis of (([1,1'-biphenyl]-4-yloxy)imino)- ⁇ 4 -sulfanone
  • O-([1,1'-biphenyl]-4-yl)hydroxylamine 26 g, 140 mmol
  • diethyl ether 1000 mL
  • triethylamine 39.1 mL, 281 mmol
  • thionyl chloride 10.76 mL, 147 mmol
  • Step 3 Synthesis of N-ethyl-N-methylmethanesulfonimidamide
  • methylmagnesium iodide 4.32 mL, 8.65 mmol
  • N- methylethanamine (0.511 g, 8.65 mmol) was added dropwise over 5 min at -78 °C and the mixture stirred at the same temperature for further 15 min. Then the reaction mixture was stirred at 25 °C for another1 h. After the completion of the reaction, the reaction mixture was quenched with a saturated ammonium chloride solution (20 mL) and extracted with ethyl acetate (25 mL x 3).
  • Step 4 Synthesis of N-((1S)-1-(1-(4-(((ethyl(methyl)amino)(methyl)(oxo)- ⁇ 6 - sulfaneylidene)amino)pyridin-2-yl)-1H-1,2,4-triazol-5-yl)ethyl)-3,5-bis(trifluoromethyl)benzamide (200)
  • (S)-N-(1-(1-(4-iodopyridin-2-yl)-1H-1,2,4-triazol-5-yl)ethyl)-3,5- bis(trifluoromethyl)benzamide (0.35 g, 0.630 mmol) in 1,4-dioxane (5 mL), N-ethyl-N- methylmethanesulfonimidamide (0.129 g, 0.946 mmol) and potassium phosphate tribasic (0.401 g, 1.9 mmol
  • reaction mixture was degassed with nitrogen for 15 min, followed by the addition of xantphos (0.128 g, 0.221 mmol) and tris(dibenzylideneacetone)dipalladium(0) (0.085 g, 0.095 mmol)
  • xantphos 0.128 g, 0.221 mmol
  • tris(dibenzylideneacetone)dipalladium(0) 0.085 g, 0.095 mmol
  • reaction mixture was filtered through a pad of celite.
  • the filtrate was concentrated under reduced pressure to obtain a residue which was dissolved in acetonitrile (60 mL) followed by the dropwise addition of concentrated hydrochloric acid (20 mL).
  • the resulting reaction mixture was allowed to stir at 25 °C for 18 h.
  • the reaction mixture was filtered through a pad of celite.
  • the filterate was diluted with water (200 mL) and extracted with ethyl acetate (200 mL x 3).
  • Step-2 Synthesis of 1-(3-chloropyrazin-2-yl)ethan-1-amine: To a stirred solution of 1-(3-chloropyrazin-2-yl)ethan-1-one (16 g, 102 mmol) in methanol (150 mL), ammonium acetate (118 g, 1.538 mol) was added, and the resulting mixture was stirred for 10 min at 25 °C. Then sodium cyanoborohydride (NaBH 3 CN), (9.6 g, 153 mmol) was added at 25 °C and the reaction mixture was stirred for further 12 h. After the completion of the reaction, the reaction mixture was concentrated under reduced pressure to obtain a crude residue.
  • NaBH 3 CN sodium cyanoborohydride
  • Step-3 Synthesis of N-(1-(3-chloropyrazin-2-yl)ethyl)-3,5-bis(trifluoromethyl)benzamide: To a stirred solution of 3,5-bis(trifluoromethyl)benzoic acid (7.5 g, 29.1 mmol) in N,N-dimethylformamide (50 mL), 1-[bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxide hexafluorophosphate (11.1 g, 29.1 mmol) were slowly added, and the resulting reaction mixture was stirred at 25 °C for 0.5 h.
  • N,N-diisopropylethylamine (15.2 mL, 87.3 mmol) and a solution of 1-(3- chloropyrazin-2-yl)ethan-1-amine (3.5 g, 22.4 mmol) in N,N-dimethylformamide (20 mL) were added and the reaction mixture was allowed to be stirred at 25 °C for further 16 h. After the completion of the reaction, the reaction mixture was diluted with water (100 mL) and the aqueous layer was extracted with ethyl acetate (200 mL x 3).
  • Step-4 Synthesis of N-(1-(3-(5-bromo-1H-pyrazol-1-yl)pyrazin-2-yl)ethyl)-3,5- bis(trifluoromethyl)benzamide: To a stirred solution of N-(1-(3-chloropyrazin-2-yl)ethyl)-3,5-bis(trifluoromethyl)benzamide (590 mg, 1.484 mmol), 3-bromo-1H-pyrazole (327 mg, 2.225 mmol) in N,N-dimethylformamide (5 mL), potassium carbonate (615 mg, 4.45 mmol) was added slowly, and the resulting reaction mixture was stirred at 130 °C for 2 h under microwave irradiation.
  • Step-5 Synthesis of N-(1-(3-(5-((dimethyl(oxo)- ⁇ 6 -sulfaneylidene)amino)-1H-pyrazol-1-yl)pyrazin-2- yl)ethyl)-3,5-bis(trifluoromethyl)benzamide (196)
  • a stirred solution of N-(1-(3-(5-bromo-1H-pyrazol-1-yl)pyrazin-2-yl)ethyl)-3,5- bis(trifluoromethyl)benzamide 250 mg, 0.492 mmol
  • iminodimethyl- ⁇ 6 -sulfanone 68.7 mg, 0.738 mmol
  • Step-2 (S)-3-chloro-N-(1-(1-(5-(((dimethyl(oxo)- ⁇ 6 -sulfaneylidene)amino)methyl)pyridin-2-yl)-1H- 1,2,4-triazol-5-yl)ethyl)-5-(trifluoromethyl)benzamide (187)
  • iminodimethyl- ⁇ 6 -sulfanone 86 mg, 0.921 mmol
  • acetonitrile 5 mL
  • potassium carbonate 127 mg, 0.921 mmol
  • (S)-N-(1-(1-(5- (bromomethyl)pyridin-2-yl)-1H-1,2,4-triazol-5-yl)ethyl)-3-chloro-5-(trifluoromethyl)benzamide 300 mg, 0.614 mmol
  • the compounds of formula (I) show insecticidal activities which are exerted with respect to numerous insects that attack on important agricultural crops.
  • the compounds of the present invention were assessed for their activity as described in the following tests: BIOLOGY EXAMPLES: Example A: Helicoverpa armigera The diet incorporation method was used, in which the required quantity of the test compound was weighed and dissolved in a tube containing a solvent solution. The tube was put on a vortex at 2000 rpm for 90 min for proper mixing. Semi-synthetic diet was incorporated into this solution when the temperature was approximately 50 °C in the bioassay containers. Compound and diet were stirred thoroughly for proper mixing and allowed to cool for 30 min.
  • the solidified diet was cut into equal pieces, and then each piece was transferred into one cell of a bio-assay tray.
  • a single starved third instar larva was released into each of the cells of the bioassay trays and the tray was covered with a lid.
  • the bio-assay trays were then kept under laboratory conditions at a temperature of 25 °C and a relative humidity of 70%. Observations on dead, moribund and alive larvae were recorded 96 h after the release of the larvae. Percent mortality was calculated by combining dead and moribund larvae and comparing the result to the one of the untreated control.
  • Example B Spodoptera litura The diet incorporation method was used, in which the required quantity of the test compound was weighed and dissolved in a tube containing a solvent solution. The tube was put on a vortex at 2000 rpm for 90 min for proper mixing.
  • Semi-synthetic diet was incorporated into this solution when the temperature was approximately 50 °C in the bioassay containers. Compound and diet were stirred thoroughly for proper mixing and allowed to cool for 30 min. The solidified diet was cut into equal pieces, and then each piece was transferred into one cell of a bio-assay tray. A single starved third instar larva was released into each of the cells of the bioassay trays and the tray was covered with a lid. The bio-assay trays were then kept under laboratory conditions at a temperature of 25 °C and a relative humidity of 70%. Observations on dead, moribund and alive larvae were recorded 96 h after the release of the larvae.
  • Percent mortality was calculated by combining dead and moribund larvae and comparing the result to the one of the untreated control.
  • Example C Plutella xylostella The leaf dip method was used for testing, wherein the required quantity of the compound was weighed and dissolved in a tube containing a solvent solution.
  • the tube was put on a vortex at 2000 rpm for 90 min for proper mixing, then the mixture was diluted with a 0.01% Triton-X solution to the desired test concentration.
  • Cabbage leaves were dipped in the compound solution for 10 seconds, shade dried for 20 min and then transferred into the cells of bioassay trays.
  • a single second instar larva was released into each cell and the tray was covered with a lid.
  • the bio-assay trays were then kept under laboratory conditions at a temperature of 25 °C and a relative humidity of 70%. Observations on dead, moribund and alive larvae were recorded 72 h after the release. Percent mortality was calculated by combining dead and moribund larvae and comparing the result to the one of the untreated control.
  • Example D Bemisia tabaci
  • the leaf dip method was used for testing, wherein the required quantity of the compound was weighed and dissolved in a tube containing a solvent solution. The tube was put on a vortex at 2000 rpm for 90 min for proper mixing, then the mixture was diluted with a 0.01% Triton-X solution to the desired test concentration. Brinjal leaves were dipped in the compound solution for 10 seconds; shade dried for 20 min and then placed, with the abaxial side of the leaf up, on 4 ml of a solidified 1 % agar-agar solution in respective perforated container caps.
  • the tube was put on a vortex at 2000 rpm for 90 min for proper mixing, then the mixture was diluted with a 0.01% Triton-X solution to the desired test concentration.
  • Capsicum leaves were dipped in the compound solution for 10 seconds, shade dried for 20 min and then placed, with the abaxial side of the leaf up, in single cells of a bio-assay tray containing 4 ml of a solidified 1 % agar-agar solution.
  • Known numbers of third instar nymphs, collected in petri plates, were released into the cell with the treated leaf and the cell was covered with a perforated lid for better aeration.
  • the trays were kept in a plant growth chamber at a temperature of 25 °C and a relative humidity of 70%.
  • Example F Nilaparvata lugens
  • the seedling dip method was used for testing, wherein the required quantity of the compound was weighed and dissolved in a tube containing a solvent solution. The tube was put on a vortex at 2000 rpm for 90 min for proper mixing, then the mixture was diluted with a 0.01% Triton-X solution to the desired test concentration. Paddy seedlings were dipped in the compound solution for 10 seconds, shade dried for 20 min and then the seedlings were placed in glass test tubes with the roots kept in water. 15 third instar nymphs were released into each test tube, the tubes were covered with a lid and kept in a plant growth chamber at a temperature of 25 °C and relative humidity of 75%.

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Abstract

La présente invention concerne des composés carboxamides aromatiques contenant des sulfoximines/sulfilimine de formule (I), formule (I) dans laquelle, le cycle A, le cycle B, le cycle C, R2, R3a et R3b sont tels que définis dans la description détaillée. La présente invention concerne en outre des procédés pour leur préparation et l'utilisation des composés de formule (I) en tant qu'agent de lutte contre les organismes nuisibles.
PCT/IB2022/058389 2021-09-08 2022-09-07 Composés carboxamide aromatiques contenant des sulfoximines/sulfilimine et leur utilisation Ceased WO2023037249A1 (fr)

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EP4455137A1 (fr) 2023-04-24 2024-10-30 Basf Se Composés de pyrimidine pour la lutte contre les nuisibles invertébrés
WO2024223373A1 (fr) 2023-04-24 2024-10-31 Basf Se Composés de pyrimidine pour la lutte contre les invertébrés nuisibles
EP4488270A1 (fr) 2023-07-06 2025-01-08 Basf Se Composés triazoles pour la lutte contre les invertébrés nuisibles
EP4488273A1 (fr) 2023-07-06 2025-01-08 Basf Se Composés triazoles pour la lutte contre les invertébrés nuisibles
EP4488269A1 (fr) 2023-07-06 2025-01-08 Basf Se Composés triazoles pour la lutte contre les invertébrés nuisibles
WO2025008247A1 (fr) 2023-07-06 2025-01-09 Basf Se Composés de triazole pour la lutte contre les invertébrés nuisibles
WO2025008249A1 (fr) 2023-07-06 2025-01-09 Basf Se Composés triazoles pour la lutte contre les invertébrés nuisibles
WO2025008250A1 (fr) 2023-07-06 2025-01-09 Basf Se Composés de triazole pour la lutte contre les invertébrés nuisibles
WO2025045835A1 (fr) 2023-08-30 2025-03-06 Syngenta Crop Protection Ag Composés d'oxoindole à action pesticide
WO2025045838A2 (fr) 2023-08-31 2025-03-06 Syngenta Crop Protection Ag Composés de benzisothiazole à action pesticide
WO2025045837A1 (fr) 2023-08-31 2025-03-06 Syngenta Crop Protection Ag Composés d'indazole à action pesticide
EP4574819A1 (fr) 2023-12-22 2025-06-25 Basf Se Composés de diazinone pour la lutte contre les invertébrés nuisibles
WO2025131957A1 (fr) 2023-12-22 2025-06-26 Basf Se Composés de diazinon pour la lutte contre les invertébrés nuisibles
WO2025186065A1 (fr) 2024-03-05 2025-09-12 Bayer Aktiengesellschaft Dérivés de (aza)quinoxaline substitués par hétéroaryle utilisés en tant que pesticides

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WO2019201835A1 (fr) 2018-04-17 2019-10-24 Bayer Aktiengesellschaft Composés hétéroaryle-triazole et hétéroaryle-tétrazole utilisés en tant que pesticides
WO2019206799A1 (fr) 2018-04-25 2019-10-31 Bayer Aktiengesellschaft Nouveaux composés hétéroaryle-triazole et hétéroaryle-tétrazole utilisés en tant que pesticides
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Cited By (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP4455137A1 (fr) 2023-04-24 2024-10-30 Basf Se Composés de pyrimidine pour la lutte contre les nuisibles invertébrés
WO2024223373A1 (fr) 2023-04-24 2024-10-31 Basf Se Composés de pyrimidine pour la lutte contre les invertébrés nuisibles
EP4488270A1 (fr) 2023-07-06 2025-01-08 Basf Se Composés triazoles pour la lutte contre les invertébrés nuisibles
EP4488273A1 (fr) 2023-07-06 2025-01-08 Basf Se Composés triazoles pour la lutte contre les invertébrés nuisibles
EP4488269A1 (fr) 2023-07-06 2025-01-08 Basf Se Composés triazoles pour la lutte contre les invertébrés nuisibles
WO2025008247A1 (fr) 2023-07-06 2025-01-09 Basf Se Composés de triazole pour la lutte contre les invertébrés nuisibles
WO2025008249A1 (fr) 2023-07-06 2025-01-09 Basf Se Composés triazoles pour la lutte contre les invertébrés nuisibles
WO2025008250A1 (fr) 2023-07-06 2025-01-09 Basf Se Composés de triazole pour la lutte contre les invertébrés nuisibles
WO2025045835A1 (fr) 2023-08-30 2025-03-06 Syngenta Crop Protection Ag Composés d'oxoindole à action pesticide
WO2025045838A2 (fr) 2023-08-31 2025-03-06 Syngenta Crop Protection Ag Composés de benzisothiazole à action pesticide
WO2025045837A1 (fr) 2023-08-31 2025-03-06 Syngenta Crop Protection Ag Composés d'indazole à action pesticide
WO2025045838A3 (fr) * 2023-08-31 2025-05-15 Syngenta Crop Protection Ag Composés de benzisothiazole à action pesticide
EP4574819A1 (fr) 2023-12-22 2025-06-25 Basf Se Composés de diazinone pour la lutte contre les invertébrés nuisibles
WO2025131957A1 (fr) 2023-12-22 2025-06-26 Basf Se Composés de diazinon pour la lutte contre les invertébrés nuisibles
WO2025186065A1 (fr) 2024-03-05 2025-09-12 Bayer Aktiengesellschaft Dérivés de (aza)quinoxaline substitués par hétéroaryle utilisés en tant que pesticides

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