WO2022064453A1 - Nematocidal compounds and use thereof - Google Patents

Nematocidal compounds and use thereof Download PDF

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Publication number
WO2022064453A1
WO2022064453A1 PCT/IB2021/058748 IB2021058748W WO2022064453A1 WO 2022064453 A1 WO2022064453 A1 WO 2022064453A1 IB 2021058748 W IB2021058748 W IB 2021058748W WO 2022064453 A1 WO2022064453 A1 WO 2022064453A1
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Prior art keywords
pyrazol
trifluorobut
acetate
methyl
compound
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PCT/IB2021/058748
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French (fr)
Inventor
Robindro Singh SARANGTHEM
Vishal A. MAHAJAN
Rushikesh Deepak JADHAV
Vikram Singh JHALA
Amol Dnyaneshwar KALWAGHE
Kiran MORYA
Alexander G.M. KLAUSENER
Jagadish Pabba
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Pi Industries Ltd.
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Publication of WO2022064453A1 publication Critical patent/WO2022064453A1/en

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/50—1,3-Diazoles; Hydrogenated 1,3-diazoles
    • 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
    • A01N43/50—1,3-Diazoles; Hydrogenated 1,3-diazoles
    • A01N43/52—1,3-Diazoles; Hydrogenated 1,3-diazoles condensed with carbocyclic rings, e.g. benzimidazoles
    • 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
    • A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
    • 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
    • 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
    • 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
    • A01N43/713—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with four or more nitrogen atoms as the only ring hetero atoms
    • 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
    • A01P5/00—Nematocides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D231/16—Halogen atoms or nitro radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/54—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings condensed with carbocyclic rings or ring systems
    • C07D231/56—Benzopyrazoles; Hydrogenated benzopyrazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D233/68—Halogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
    • C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
    • C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
    • C07D235/06—Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D249/04—1,2,3-Triazoles; Hydrogenated 1,2,3-triazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/16—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms condensed with carbocyclic rings or ring systems
    • C07D249/18—Benzotriazoles

Definitions

  • the present invention relates to novel nematicidal compounds. More particularly, the present invention relates to a N-linked heterocyclic fluoroalkenyl compounds of formula (I) and to a process for the preparation thereof. The present invention further relates to the use of the compounds of formula (I) as crop protection agents for the control of pests such as plant parasitic nematodes.
  • WO2019186498, WO2020075107, WO2003042153 and WO9708130 disclose fluoroalkenyl heterocyclic compounds showing nematicidal activity, wherein heterocycles containing heteroatoms such as nitrogen, sulfur and oxygen are attached through a C-linker to fluoroalkenyl groups.
  • WO2020157668 disclose caffeine or theophylline derivatives having nematicidal activity.
  • the control of damages to crops caused by phytopathogenic microorganisms and pests is extremely important for achieving high crop efficiency. For instance, damage caused by plant diseases to ornamental, vegetable, field, cereal and fruit crops can lead tosignificant reduction in productivity and thereby result in increased cost for the consumer.
  • the present invention provides a novel N-linked heterocyclic fluoroalkenyl compoundof formula (I), Formula (I) wherein, R 1 , R 2 , R 3 , ring A and Y are as defined in the detailed description.
  • the present invention provides a process for the preparation of compounds of formula (I).
  • the present invention provides a use of the compounds of formula (I) as crop protection agent for the control of phytoparasitic organisms, especially of plant parasitic nematodes.
  • DEFINITIONS The terminologies used in the present disclosure are for illustrative purpose only and in no manner limit the scope of the present invention disclosed in the present disclosure.
  • the terms “comprises”, “comprising”, “includes”, “including”, “has”, “having”, “contains”, “containing”, “characterized by” or any other variation thereof, are intended to cover a non-exclusive inclusion, subject to any limitation explicitly indicated.
  • compositions, mixture, process or method that comprises a list of elements is not necessarily limited to only those elements but may include other elements not expressly listed or inherent to such composition, mixture, process or method.
  • 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 “consisting essentially of” occupies a middle ground between “comprising” and “consisting of”.
  • “or” refers to an inclusive “or” and not to an exclusive “or”.
  • a condition A “or” B is satisfied by any one of the following: A is true (or present) and B is false (or not present), A is false (or not present) and B is true (or present), and both A and B are true (or present).
  • the indefinite articles “a” and “an” preceding an element or component of the present invention are intended to be nonrestrictive regarding the number of instances (i.e. occurrences) of the element or component. Therefore “a” or “an” should be read to include one or at least one, and the singular word form of the element or component also includes the plural unless the number is obviously meant to be singular.
  • the term “pesticide” in each case also always comprises the term “crop protection agent”.
  • 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 (Trematoda), acanthocephala and tapeworms (Cestoda).
  • invertebrate pest control means inhibition of invertebrate pest development (including mortality, feeding reduction, and/or mating disruption), and related expressions are defined analogously.
  • agronomic refers to the production of field crops such as for food and fiber and includes the growth of corn, soybeans and other legumes, rice, cereal (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 fruit (berries, cherries) and other specialty crops (e.g., canola, sunflower, olives).
  • wheat 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 e.g., sweet potatoes, grapes, cotton, tree fruits (e.g.
  • 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.
  • a compound of the present invention typically in the form of a composition formulated for veterinary use, to the animal to be protected.
  • parasitic 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 necrosis, death, retarded growth, diminished mobility or lessened ability to remain on or in the host animal, reduced feeding and inhibition of reproduction.
  • 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). Additionally, the person skilled in the art knows processes or methods or technology to separate, enrich, and/or to selectively prepare said isomers.
  • 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 15 alkyl, preferably C 1 to C 10 alkyl, more preferably C 1 to C 6 alkyl.
  • Non limiting examples of 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-methylpropy
  • 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.
  • alkenyl used either alone or in compound words includes straight-chain or branched C 2 to C 15 alkenes, preferably C 2 to C 10 alkenes, more preferably C 2 to C 6 alkenes.
  • Non limiting 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, 1-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, 1- methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, 1-methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl, 1,1-dimethyl-2-propenyl, 1,2-dimethyl-1-propenyl, 1,2-dimethyl-2 -propenyl, 1- ethyl-1-propenyl, 1-ethy
  • 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 branched or straight-chain C 2 to C 24 alkynes, preferably C 2 to C 15 alkynes, more preferably C 2 to C 10 alkynes, most preferably C 2 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-pentynyl, 3-pentynyl, 4-pentynyl, 1-methyl-2- butynyl, 1-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, 1- methyl-3-pentynyl, 1-methyl-4-pentynyl, 2-methyl-3-pentynyl, 2-methyl-4-pent
  • 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.
  • cyclic alkyl or “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 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. This definition also applies to cycloalkynyl as a part of a composite substituent, for example cycloalkynylalkyl etc., unless specifically defined elsewhere.
  • cycloalkoxy cycloalkenyloxy
  • cycloalkoxy cycloalkenyloxy
  • Non limiting examples of cycloalkoxy include cyclopropyloxy, cyclopentyloxy and cyclohexyloxy. This definition also applies to cycloalkoxy as a part of a composite substituent, for example cycloalkoxy alkyl etc., unless specifically defined elsewhere.
  • alkoxy used either alone or in compound words included C 1 to C 15 alkoxy, preferably C 1 to C 10 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 1-ethyl-2-methylpropoxy and the different isomers.
  • alkoxy as a part of a composite substituent, for example haloalkoxy, alkynylalkoxy, etc., unless specifically defined elsewhere.
  • alkylthio includes branched or straight-chain alkylthio moieties such as methylthio, ethylthio, propylthio, 1-methylethylthio, butylthio, 1-methylpropylthio, 2-methylpropylthio, 1,1- dimethylethylthio, pentylthio, 1-methylbutylthio, 2-methylbutylthio, 3-methylbutylthio, 2,2- dimethylpropylthio, 1-ethylpropylthio, hexylthio, 1,1-dimethylpropylthio, 1,2-dimethylpropylthio, 1- methylpentylthio, 2-methylpentylthio, 3-methylpentylthio, 4-methylpentylthio,
  • 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 .
  • 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 and “haloalkynyl” are defined analogously except that, instead of alkyl groups, alkenyl and alkynyl groups are present as a part of the substituent.
  • haloalkoxy means straight-chain or branched alkoxy groups where some or all of the hydrogen atoms in these groups may be replaced by halogen atoms as specified above.
  • Non-limiting examples of haloalkoxy include chloromethoxy, bromomethoxy, dichloromethoxy, trichloromethoxy, fluoromethoxy, difluoromethoxy, trifluoromethoxy, chlorofluoromethoxy, dichlorofluoromethoxy, chlorodifluoromethoxy, 1-chloroethoxy, 1-bromoethoxy, 1-fluoroethoxy, 2-fluoroethoxy, 2,2- difluoroethoxy, 2,2,2-trifluoroethoxy, 2-chloro-2-fluoroethoxy, 2-chloro-2,2-difluoroethoxy, 2,2- dichloro-2-fluoroethoxy, 2,2,2-trichloroethoxy, pentafluoroethoxy and 1,1,1-trifluoroprop-2-oxy.
  • haloalkylthio or haloalkylsulfanyl means straight-chain or branched alkylthio groups where some or all of the hydrogen atoms in these groups may be replaced by halogen atoms as specified above.
  • Non-limiting examples of haloalkylthio include chloromethylthio, bromomethylthio, dichloromethylthio, trichloromethylthio, fluoromethylthio, difluoromethylthio, trifluoromethylthio, chlorofluoromethylthio, dichlorofluoromethylthio, chlorodifluoromethylthio, 1-chloroethylthio, 1- bromoethylthio, 1- fluoroethylthio, 2-fluoroethylthio, 2,2-difluoroethylthio, 2,2,2-trifluoroethylthio, 2- chloro-2- fluoroethylthio, 2-chloro-2,2-difluoroethylthio, 2,2-dichloro-2-fluoroethylthio, 2,2,2- trichloroethylthio, pentafluoroethylthio and 1,1,1-triflu
  • haloalkylthio as a part of a composite substituent, for example haloalkylthioalkyl etc., unless specifically defined elsewhere.
  • haloalkylsulfinyl include CF 3 S(O), CCl 3 S(O), CF 3 CH 2 S(O) and CF 3 CF 2 S(O).
  • haloalkylsulfonyl include CF 3 S(O) 2 , CCl 3 S(O) 2 , CF 3 CH 2 S(O) 2 and CF 3 CF 2 S(O) 2 .
  • alkylsulfinyl include but are not limited to methylsulphinyl, ethylsulphinyl, propylsulphinyl, 1-methylethylsulphinyl, butylsulphinyl, 1-methylpropylsulphinyl, 2- methylpropylsulphinyl, 1,1-dimethylethylsulphinyl, pentylsulphinyl, 1-methylbutylsulphinyl, 2- methylbutylsulphinyl, 3-methylbutylsulphinyl, 2,2-dimethylpropylsulphinyl, 1-ethylpropylsulphinyl, hexylsulphinyl, 1,1-dimethylpropylsulphinyl, 1,2-dimethylpropylsulphinyl, 1-methylpentylsulphinyl, 2-methylpentylsulphinyl, 3-methylpentylsulphin
  • alkylsulfonyl include but are not limited to methylsulphonyl, ethylsulphonyl, propylsulphonyl, 1-methylethylsulphonyl, butylsulphonyl, 1-methylpropylsulphonyl, 2-methylpropylsulphonyl, 1,1-dimethylethylsulphonyl, pentylsulphonyl, 1-methylbutylsulphonyl, 2- methylbutylsulphonyl, 3-methylbutylsulphonyl, 2,2-dimethylpropylsulphonyl, 1- ethylpropylsulphonyl, hexylsulphonyl, 1,1-dimethylpropylsulphonyl, 1,2-dimethylpropylsulphonyl, 1- methylpentylsulphonyl, 2-methylpentylsulphonyl, 3-methylpentylsulfonyl,
  • arylsulfonyl includes Ar-S(O) 2 , wherein Ar can be any carbocyle or heterocylcle. This definition also applies to alkylsulphonyl as a part of a composite substituent, for example alkylsulphonylalkyl etc., unless defined elsewhere.
  • the term “ring” or “ring system” as a component of formula I is carbocyclyl or heterocyclyl.
  • ring system denotes one or more rings.
  • aromatic indicates that the Hueckel rule is satisfied and the term “non-aromatic” indicates that the Hueckel rule is not satisfied.
  • carrier or “carbocyclic” or “carbocyclyl” include “aromatic carbocyclic ring system” and “nonaromatic carbocylic ring system” 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.
  • 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.
  • non-aromatic heterocycle or “non-aromatic heterocyclic” means three- to fifteen- membered, preferably three- to twelve-membered, saturated or partially unsaturated heterocycle containing one to four heteroatoms from the group of oxygen, nitrogen and sulphur: mono, bi- or tricyclic heterocycles which contain, in addition to 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, tetrahydrofuranyl, tetrahydrothienyl, pyrrolidinyl, isoxazolidinyl, isothiazolidinyl, pyrazolidinyl, oxazolidin
  • heterocyclyl as a part of a composite substituent, for example heterocyclylalkyl etc., unless specifically defined elsewhere.
  • heteroaryl or "aromatic heterocyclic” means 5 -membered, fully unsaturated monocyclic ring system containing one to four heteroatoms selected 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 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, thiazoly
  • 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. For example, C 1 -C 3 alkoxy designates methoxy through propoxy.
  • the present invention provides a compound of formula (I), wherein ring A represents ring system selected from A8 to A12 wherein A may be optionally substituted with one or more R 4 ;
  • the present invention provides a compound of formula (I), wherein prefereably ring A is selected from A1, A2, A6 and A7 wherein A may be optionally substituted with one or more R 4 ;
  • the present invention provides a compound of formula (I), wherein preferred compounds selected from 4,4-difluorobut-3-en-1-yl 2-(5-methyl-3-(trifluoromethyl)-1H-pyrazol-1- yl)acetate; 4,4-difluorobut-3-en-1-yl 2-(3,5-bis(trifluoromethyl)-1H-pyrazol-1-yl)acetate; 4,4- difluorobut-3-en-1-yl 2-(3,5-dimethyl-1H-pyrazol-1-yl)acetate; 4,4-difluorobut-3-en-1-yl 2-(4- methyl-1H-pyrazol-1-yl)acetate; 4,4-difluorobut-3-en-1-yl 2-(3,5-bis(difluoromethyl)-1H-pyrazol-1- yl)acetate; 3,4,4-trifluorobut-3-en-1-yl 2-(5-methyl-3-(trifluor
  • a compound of formula 4 can be prepared by alkylation of a compound of formula 2 with a alkyl haloacetate compound of formula 3 in the presence of an organic or an inorganic base such as for instance potassium carbonate or cesium carbonate in the presence of a suitable solvent such as for instance acetonitrile or N,N-dimethylformamide, usually under heating conditions. Subsequently the compound of formula 4 is hydrolysed to obtain a compound of formula 5 in presence of a suitable acid or base.
  • an organic or an inorganic base such as for instance potassium carbonate or cesium carbonate
  • a suitable solvent such as for instance acetonitrile or N,N-dimethylformamide
  • Suitable acids which can be used for this hydrolysis are selected from hydrochloric acid or trifluoroacetic acid, whereas a suitable base which can be used for the hydrolysis may be selected from sodium hydroxide or lithium hydroxide in the presence of a suitable solvent such as for instance tetrahydrofuran, 1,4-dioxane, methanol or water.
  • a compound of formula 1a can be prepared by alkylation of a compound of formula 5 with a fluorobutenyl halide compound of formula 6 in the presence of an organic or inporganic base such as N,N-diisopropylethylamine, potassium carbonate or cesium carbonate; in suitable solvents such as acetonitrile and N,N-dimethyl formamide, usually under heating conditions.
  • an organic or inporganic base such as N,N-diisopropylethylamine, potassium carbonate or cesium carbonate
  • suitable solvents such as acetonitrile and N,N-dimethyl formamide
  • a compound of formula 1b can be prepared by an amide coupling reaction of a compound of formula 5 with an amine of formula 6 using various coupling reagents such as N-(3- Dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (EDCI), 1- [Bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxid hexafluorophosphate (HATU), or halogenating reagent such as SOCl 2 , SO 2 Cl 2 , COCl 2 , X 2 , methanesulfonyl chloride, preferably in the presence of a base such as triethylamine and diisopropylethyl amine.
  • EDCI N-(3- Dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride
  • HATU 1- [Bis(dimethylamino)
  • the compound of formula 1c can be prepared by alkylation of a compound of formula 1b with an alkyl halide in the presence of a base such as for instance potassium carbonate, cesium carbonate and sodium hydride in the presence of a suitable solvent such as acetonitrile and N,N-dimethylformamide, usually betweent room temperature and heating conditions.
  • a base such as for instance potassium carbonate, cesium carbonate and sodium hydride
  • a suitable solvent such as acetonitrile and N,N-dimethylformamide, usually betweent room temperature and heating conditions.
  • Any of the compounds according to the invention can exist in one or more optical, geometric or chiral isomer forms depending on the number of asymmetric centres in the compound.
  • the invention thus relates equally to all the optical isomers and to their racemic or scalemic mixtures (the term “scalemic” denotes a mixture of enantiomers in different proportions), and to the mixtures of all the possible stereoisomers, in all proportions.
  • the diastereoisomers and/or the optical isomers can be separated according to the methods which are known per se by a person ordinary skilled in the art. Any of the compounds according to the invention can also exist in one or more geometric isomer forms depending on the number of double bonds in the compound.
  • the invention thus relates equally to all geometric isomers and to all possible mixtures, in all proportions.
  • the geometric isomers can be separated according to general methods, which are known per se by a person ordinary skilled in the art.
  • any of the compounds according to the invention can also exist in one or more amorphic or isomorphic or polymorphic forms, depending on their preparation, purification storage and various other influencing factors.
  • the invention thus relates all the possible amorphic, isomorphic and polymorphic forms, in all proportions.
  • the amorphic, isomorphic and polymorphic forms can be prepared and/or separated and/or purified according to general methods, which are known per se by a person ordinary skilled in the art. There is a large number of suitable known standard methods, such as alkylation, halogenation, acylation, amidation, oximation, oxidation and reduction. The choice of the preparation methods which are suitable are depending on the properties (reactivity) of the substituents in the intermediates.
  • the reactants can be reacted in the presence of a base.
  • suitable bases are alkali metal or alkaline earth metal hydroxides, alkali metal or alkaline earth metal hydrides, alkali metal or alkaline earth metal amides, alkali metal or alkaline earth metal alkoxides, alkali metal or alkaline earth metal acetates, alkali metal or alkaline earth metal carbonates, alkali metal or alkaline earth metal dialkylamides or alkali metal or alkaline earth metal alkylsilylamides, alkylamines, alkylenediamines, free or N-alkylated saturated or unsaturated cycloalkylamines, basic heterocycles, ammonium hydroxides and carbocyclic amines.
  • Examples which may be mentioned are sodium hydroxide, sodium hydride, sodium amide, sodium methoxide, sodium acetate, sodium carbonate, potassium tert-butoxide, potassium hydroxide, potassium carbonate, potassium hydride, lithium diisopropylamide, potassium bis(trimethylsilyl)amide, calcium hydride, triethylamine, N,N-diisopropylethylamine, triethylenediamine, cyclohexylamine, N- cyclohexyl-N,N-dimethylamine, N,N-diethylaniline, pyridine, 4-(N,N-dimethylamino)pyridine, quinuclidine, N-methylmorpholine, benzyltrimethylammonium hydroxide and 1,8- diazabicyclo[5.4.0]undec-7-ene (DBU).
  • DBU 1,8- diazabicyclo[5.4.0]undec-7-ene
  • the reaction according to scheme-1 to scheme-3 is preferably carried out in a solvent selected from standard solvents which are inert under the prevailing reaction conditions.
  • a solvent selected from standard solvents which are inert under the prevailing reaction conditions.
  • aliphatic, alicyclic or aromatic hydrocarbons such as petroleum ether, hexane, toluene; halogenated hydrocarbons, such as, chlorobenzene, dichloromethane, chloroform, carbon tetrachloride or dichloroethane; ethers, such as, diethyl ether, diisopropyl ether, methyl t-butyl ether (MTBE), dioxane, tetrahydrofuran or 1,2-dimethoxyethane; nitriles, such as, acetonitrile or propionitrile, or; amides, such as, N,N-dimethylformamide (DMF), N,N-dimethylacetamide, N-methylf
  • the reactants can be reacted with each other as such, i.e. without adding a solvent or diluent.
  • the reaction is advantageously carried out in a temperature range from approximately -80 °C to approximately +140 °C, preferably from approximately -30 °C to approximately +100 °C, in many cases in the range between ambient temperature and approximately +80 °C.
  • a compound of formula (I) can be converted in a manner known per se into another compound of formula (I) by replacing one or more substituents of the starting compound of formula (I) in the customary manner by (an)other substituent(s) according to the invention.
  • Salts of compounds of formula (I) can be prepared in a manner known per se.
  • acid addition salts of compounds of formula (I) are obtained by treatment with a suitable acid or a suitable ion exchanger reagent and salts with bases are obtained by treatment with a suitable base or with a suitable ion exchanger reagent.
  • a salt is chosen depending on its tolerances for compound's use, such as agricultural or physiological tolerance.
  • Salts of compounds of formula (I) can be converted in the customary manner into the free compounds I, acid addition salts, for example, by treatment with a suitable basic compound or with a suitable ion exchanger reagent and salts with bases, for example, by treatment with a suitable acid or with a suitable ion exchanger reagent.
  • Salts of compounds of formula (I) can be converted in a manner known per se into other salts of compounds of formula (I), acid addition salts, for example, into other acid addition salts, for example by treatment of a salt of inorganic acid such as hydrochloride with a suitable metal salt such as a sodium, barium or silver salt, of an acid, for example with silver acetate, in a suitable solvent in which an inorganic salt which forms, for example silver chloride, is insoluble and thus precipitates from the reaction mixture.
  • a salt of inorganic acid such as hydrochloride
  • a suitable metal salt such as a sodium, barium or silver salt
  • the present invention provides use of compound of formula (I), stereoisomers, agriculturally acceptable salts, tautomers or N-oxides thereof or composition or combination thereof for controlling or preventing agricultural crops and/or horticultural crops against phytopathogenic fungi, bacteria, insects, nematodes or mites.
  • the present invention provides use of compound of formula (I), stereoisomers, agriculturally acceptable salts, tautomers or N-oxides thereof or composition or combination thereof for controlling or preventing agricultural crops and/or horticultural crops against nematodes and phytopathogenic fungi.
  • the agricultural crops are selected from cereals, corn, rice, soybean and other leguminous plants, fruits and fruit trees, 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 or ornamentals.
  • the compounds according to the invention can be used for controlling or destroying pests such as nematodes which occur in particular in plants, especially in useful plants and ornamentals in agriculture, in horticulture and in forests, or in organs, such as tubers, seeds or roots, of such plants, and in some cases even plant organs which are formed at a later point in time remain protected against these pests.
  • the compounds of formula (I) according to the invention are preventively and/or curatively valuable active ingredients in the field of pest control, even at low rates of application, which can be used against pesticide resistant pests such as nematodes. Additionally compounds of formula (I) have a very favorable biocidal spectrum and are well tolerated by warm-blooded species, fish and plants. Accordingly, the present invention also makes available a pesticidal composition comprising compounds of the invention, such as formula (I).
  • the compounds of formula (I) have, for practical purposes, a very advantageous spectrum of activity for protecting animals and useful plants against attack and damage by nematodes
  • the present invention also makes available a nematocidal composition comprising compounds of the invention, such as formula (I).
  • the compounds of the formula (I) possess potent nematicidal activity and can be used for the control of unwanted nematodes and bacteria, in agricultural or horticultural crop protection and in the protection of such materials.
  • the compounds of the formula (I) can be used as nematicides in crop protection, for example, for control of Tylenchida, Rhabditida, Dorylaimida, and Tryplonchida.
  • the compounds of the formula (I) can be used for controlling or preventing against phytopathogenic nematodes of agricultural crops and or horticultural crops.
  • the compounds of the formula (I) can be used in crop protection, wherein the agricultural crops are cereals, corn, rice, soybean and other leguminous plants, fruits and fruit trees, 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 other vegetables, and ornamentals.
  • the compounds of formula (I) are especially useful for the control of nematodes.
  • the invention also relates to a method of controlling damage to plant and parts thereof by plant parasitic nematodes (Endoparasitic, Semiendoparasitic and Ectoparasitic nematodes), especially plant parasitic nematodes such as root knot nematodes, Meloidogyne hapla, Meloidogyne incognita, Meloidogyne javanica, Meloidogyne arenaria 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, Eelono
  • the nematode species Meloidogyne spp., Heterodera spp., Rotylenchus spp., Pratylenchus spp. and Radopholus spp. can be controlled by compounds of the invention.
  • the present invention provides a composition for controlling or preventing phytopathogenic microorganisms comprising a compound of general formula (I), stereoisomer, agriculturally acceptable salts, tautomers or N-oxides thereof and one or more inert carriers.
  • the composition may additionally comprises one or more active compatible compounds selected from fungicides, insecticides, nematicides, acaricides, biopesticides, herbicides, plant growth regulators, antibiotics, nutrients or fertilizers.
  • concentration of the compound of general formula (I) ranges from 1 to 90% 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 further relates to a composition for controlling unwanted microorganisms comprising at least one of the compounds of the formula (I) and one or more inert carrier.
  • the inert carrier further comprises agriculturally suitable auxiliaries, solvents, diluents, surfactants and/or extenders and the like.
  • the present invention further relates to a composition for controlling unwanted microorganisms, comprising at least one of the compounds of the formula (I) and/or one or more active compatible compound selected from fungicides, bactericides, acaricides, insecticides, nematicides, herbicides, biopesticides, plant growth regulators, antibiotics, fertilizers and/or mixtures thereof.
  • a compound of the present invention is used in the form of a composition (e.g.formulation) containing a carrier.
  • a compound of the invention and compositions thereof can be used in various forms such as aerosol dispenser, capsule suspension, cold fogging concentrate, dustable powder, emulsifiable concentrate, emulsion oil in water, emulsion water in oil, encapsulated granule, fine granule, flowable concentrate for seed treatment, gas (under pressure), gas generating product, granule, hot fogging concentrate, macrogranule, microgranule, oil dispersible powder, oil miscible flowable concentrate, oil miscible liquid, paste, plant rodlet, powder for dry seed treatment, seed coated with a pesticide, soluble concentrate, soluble powder, solution for seed treatment, suspension concentrate (flowable concentrate), ultra-low volume (ulv) liquid, ultra-low volume (ulv) suspension, water dispersible granules or tablets, water dispersible powder for slurry treatment, water soluble granules or tablets, water soluble powder for seed treatment and wettable powder.
  • aerosol dispenser capsule suspension, cold fogging concentrate
  • dustable powder
  • a formulation typically comprises a liquid or solid carrier and optionally one or more customary formulation auxiliaries, which may be solid or liquid auxiliaries, for example unepoxidized or epoxidized vegetable oils (for example epoxidized coconut oil, rapeseed oil or soya oil), antifoams, for example silicone oil, preservatives, clays, inorganic compounds, viscosity regulators, surfactant, binders and/or tackifiers.
  • auxiliaries for example unepoxidized or epoxidized vegetable oils (for example epoxidized coconut oil, rapeseed oil or soya oil), antifoams, for example silicone oil, preservatives, clays, inorganic compounds, viscosity regulators, surfactant, binders and/or tackifiers.
  • the composition may also further comprise a fertilizer, a micronutrient donor or other preparations which influence the growth of plants as well as comprising a combination containing the compound of the invention with one or more other biologically active agents, such as bactericides, fungicides, nematicides, plant activators, acaricides, and insecticides.
  • the present invention also makes available a composition comprising a compound of the invention and an agronomical carrier and optionally one or more customary formulation auxiliaries.
  • compositions are prepared in a manner known per se, in the absence of auxiliaries for example by grinding, screening and/or compressing a solid compound of the present invention and in the presence of at least one auxiliary for example by intimately mixing and/or grinding the compound of the present invention with the auxiliary (auxiliaries).
  • auxiliaries for example by grinding, screening and/or compressing a solid compound of the present invention
  • at least one auxiliary for example by intimately mixing and/or grinding the compound of the present invention with the auxiliary (auxiliaries).
  • the grinding/milling of the compounds is to ensure specific particle size.
  • compositions for use in agriculture are emulsifiable concentrates, suspension concentrates, microemulsions, oil dispersibles, directly sprayable or dilutable solutions, spreadable pastes, dilute emulsions, soluble powders, dispersible powders, wettable powders, dusts, granules or encapsulations in polymeric substances, which comprise - at least - a compound according to the invention and the type of composition is to be selected to suit the intended aims and the prevailing circumstances.
  • suitable liquid carriers are unhydrogenated or partially hydrogenated aromatic hydrocarbons, preferably the fractions C 8 to C 12 of alkylbenzenes, such as xylene mixtures, alkylated naphthalenes or tetrahydronaphthalene, aliphatic or cycloaliphatic hydrocarbons, such as paraffins or cyclohexane, alcohols such as ethanol, propanol or butanol, glycols and their ethers and esters such as propylene glycol, dipropylene glycol ether, ethylene glycol or ethylene glycol monomethyl ether or ethylene glycol monoethyl ether, ketones, such as cyclohexanone, isophorone or diacetone alcohol, strongly polar solvents, such as N-methylpyrrolid-2-one, dimethyl sulfoxide or N,N- dimethylformamide, water, unepoxidized or epoxidized vegetable oils, such as unexpodized or epoxid
  • solid carriers which are used for example for dusts and dispersible powders are, as a rule, ground natural minerals such as calcite, talc, kaolin, montmorillonite or attapulgite.
  • ground natural minerals such as calcite, talc, kaolin, montmorillonite or attapulgite.
  • highly disperse silicas or highly disperse absorbtive polymers are also possible to add highly disperse silicas or highly disperse absorbtive polymers.
  • Suitable particulate adsorptive carriers for granules are porous types, such as pumice, brick grit, sepiolite or bentonite, and suitable non-sorptive carrier materials are calcite or sand.
  • a large number of granulated materials of inorganic or organic nature can be used, in particular dolomite or comminuted plant residues.
  • Suitable surface-active compounds are, depending on the type of the active ingredient to be formulated, non-ionic, cationic and/or anionic surfactants or surfactant mixtures which have good emulsifying, dispersing and wetting properties.
  • the surfactants mentioned below are only to be considered as examples; a large number of further surfactants which are conventionally used in the art of formulation and suitable according to the invention are described in the relevant literature.
  • Suitable non-ionic surfactants are, especially, polyglycol ether derivatives of aliphatic or (cyclo)aliphatic alcohols, of saturated or unsaturated fatty acids or of alkyl phenols which may contain approximately 3 to approximately 30 glycol ether groups and approximately 8 to approximately 20 carbon atoms in the (cyclo)aliphatic hydrocarbon radical or approximately 6 to approximately 18 carbon atoms in the alkyl moiety of the alkyl phenols.
  • water-soluble polyethylene oxide adducts with polypropylene glycol, ethylenediaminopolypropylene glycol or alkyl polypropylene glycol having 1 to approximately 10 carbon atoms in the alkyl chain and approximately 20 to approximately 250 ethylene glycol ether groups and approximately 10 to approximately 100 propylene glycol ether groups.
  • the abovementioned compounds contain 1 to approximately 5 ethylene glycol units per propylene glycol unit.
  • nonylphenoxypolyethoxyethanol castor oil polyglycol ether, polypropylene glycol/polyethylene oxide adducts, tributylphenoxypolyethoxyethanol, polyethylene glycol or octylphenoxypolyethoxyethanol.
  • fatty acid esters of polyoxyethylene sorbitan such as polyoxyethylene sorbitan trioleate.
  • the cationic surfactants are, especially, quarternary ammonium salts which generally have at least one alkyl radical of approximately 8 to approximately 22 Carbon atoms as substituents and as further substituents (unhalogenated or halogenated) lower alkyl or hydroxyalkyl or benzyl radicals.
  • the salts are preferably in the form of halides, methylsulfates or ethylsulfates.
  • Examples are stearyltrimethylammonium chloride and benzylbis(2-chloroethyl)ethylammonium bromide.
  • suitable anionic surfactants are water-soluble soaps or water-soluble synthetic surface- active compounds.
  • soaps are the alkali, alkaline earth or (unsubstituted or substituted) ammonium salts of fatty acids having approximately 10 to approximately 22 Carbon atoms, such as the sodium or potassium salts of oleic or stearic acid, or of natural fatty acid mixtures which are obtainable for example from coconut or tall oil; mention must also be made of the fatty acid methyl taurates.
  • synthetic surfactants are used more frequently, in particular fatty sulfonates, fatty sulfates, sulfonated benzimidazole derivatives or alkylaryl sulfonates.
  • the fatty sulfonates and fatty sulfates are present as alkali, alkaline earth or (substituted or unsubstituted) ammonium salts and they generally have an alkyl radical of approximately 8 to approximately 22 Carbon atoms, alkyl also to be understood as including the alkyl moiety of acyl radicals; examples which may be mentioned are the sodium or calcium salts of lignosulfonic acid, of the dodecylsulphuric ester or of a fatty alcohol sulfate mixture prepared from natural fatty acids. This group also includes the salts of the sulphuric esters and sulfonic acids of fatty alcohol/ethylene oxide adducts.
  • the sulfonated benzimidazole derivatives preferably contain 2 sulphonyl groups and a fatty acid radical of approximately 8 to approximately 22 Carbon atoms.
  • alkylarylsulfonates are the sodium, calcium or triethanolammonium salts of decylbenzenesulfonic acid, of dibutylnaphthalenesulfonic acid or of a naphthalenesulfonic acid/formaldehyde condensate.
  • suitable phosphates such as salts of the phosphoric ester of a p- nonylphenol/(4-14)ethylene oxide adduct, or phospholipids.
  • the compositions comprise 0.1 to 99%, especially 0.1 to 95%, of compound according to the present invention and 1 to 99.9%, especially 5 to 99.9%, of at least one solid or liquid carrier, it being possible as a rule for 0 to 25%, especially 0.1 to 20%, of the composition to be surfactants (% in each case meaning percent by weight).
  • surfactants % in each case meaning percent by weight.
  • Examples of foliar formulation types for pre-mix compositions are: Whereas, examples of seed treatment formulation types for pre-mix compositions are: Examples of formulation types suitable for tank-mix compositions are solutions, diluted emulsions, suspensions, or a mixture thereof, and dusts. As with the nature of the formulations, the methods of application, such as foliar, drench, spraying, atomizing, dusting, scattering, coating or pouring, are chosen in accordance with the intended objectives and the prevailing circumstances.
  • the tank-mix compositions are generally prepared by diluting with a solvent (for example, water) the one or more pre-mix compositions containing different pesticides, and optionally further auxiliaries.
  • Suitable carriers and adjuvants can be solid or liquid and are the substances ordinarily employed in formulation technology, e.g. natural or regenerated mineral substances, solvents, dispersants, wetting agents, tackifiers, thickeners, binders or fertilizers.
  • a tank-mix formulation for foliar or soil application comprises 0.1 to 20%, especially 0.1 to 15%, of the desired ingredients, and 99.9 to 80%, especially 99.9 to 85%, of a solid or liquid auxiliaries (including, for example, a solvent such as water), where the auxiliaries can be a surfactant in an amount of 0 to 20%, especially 0.1 to 15%, based on the tank-mix formulation.
  • a pre- mix formulation for foliar application comprises 0.1 to 99.9%, especially 1 to 95%, of the desired ingredients, and 99.9 to 0.1%, especially 99 to 5%, of a solid or liquid adjuvant (including, for example, a solvent such as water), where the auxiliaries can be a surfactant in an amount of 0 to 50%, especially 0.5 to 40%, based on the pre-mix formulation.
  • a solid or liquid adjuvant including, for example, a solvent such as water
  • a tank-mix formulation for seed treatment application comprises 0.25 to 80%, especially 1 to 75%, of the desired ingredients, and 99.75 to 20%, especially 99 to 25%, of a solid or liquid auxiliaries (including, for example, a solvent such as water), where the auxiliaries can be a surfactant in an amount of 0 to 40%, especially 0.5 to 30%, based on the tank-mix formulation.
  • auxiliaries including, for example, a solvent such as water
  • a pre-mix formulation for seed treatment application comprises 0.5 to 99.9%, especially 1 to 95%, of the desired ingredients, and 99.5 to 0.1%, especially 99 to 5%, of a solid or liquid adjuvant (including, for example, a solvent such as water), where the auxiliaries can be a surfactant in an amount of 0 to 50%, especially 0.5 to 40%, based on the pre-mix formulation whereas commercial products will preferably be formulated as concentrates (e.g., pre-mix composition (formulation)), the end user will normally employ diluted formulations (e.g., tank mix composition).
  • Preferred seed treatment pre-mix formulations are aqueous suspension concentrates.
  • the formulation can be applied to the seeds using conventional treating techniques and machines, such as fluidized bed techniques, the roller mill method, roto static seed treaters, and drum coaters. Other methods, such as spouted beds may also be useful.
  • the seeds may be pre sized before coating. After coating, the seeds are typically dried and then transferred to a sizing machine for sizing. Such procedures are known in the art.
  • the compounds of the present invention are particularly suited for use in soil and seed treatment applications.
  • the pre-mix compositions of the invention contain 0.5 to 99.9% especially 1 to 95%, advantageously 1 to 50%, by mass of the desired ingredients, and 99.5 to 0.1%, especially 99 to 5%, by mass of a solid or liquid adjuvant (including, for example, a solvent such as water), where the auxiliaries (or adjuvant) can be a surfactant in an amount of 0 to 50%, especially 0.5 to 40%, by mass based on the mass of the pre-mix formulation.
  • a compound of the formula (I) in a preferred embodiment, independent of any other embodiments, is in the form of a plant propagation material treating (or protecting) composition, wherein said plant propagation material protecting composition may comprises additionally a coloring agent.
  • the plant propagation material protecting composition or mixture may also comprise at least one polymer from water-soluble and water-dispersible film-forming polymers that improve the adherence of the active ingredients to the treated plant propagation material, which polymer generally has an average molecular weight of at least 10,000 to about 100,000.
  • the present invention provides a method of controlling or preventing infestation of useful plants by phytopathogenic microorganisms in agricultural crops and/or horticultural crops, wherein the compound of general formula (I) and/or stereoisomers or agriculturally acceptable salts or tautomers or N-oxides thereof or composition or combination thereof, is applied to the plants, to parts thereof or a locus thereof.
  • the present invention provides a method of controlling or preventing infestation of useful plants by phytopathogenic nematodes in agricultural crops and/or horticultural crops, wherein the compound of general formula (I) and/or stereoisomers or agriculturally acceptable salts or tautomers or N-oxides thereof or composition or combination thereof is applied to a seeds of plants.
  • the present invention provides a method of controlling or preventing phytopathogenic nematodes in agricultural crops and/or horticultural crops using the compound of general formula (I) and/or stereoisomers or agriculturally acceptable salts or tautomers or N-oxides thereof or composition or combination thereof comprising a step of applying an effective dosage of the compound or the composition or the combination, in amounts ranging from 1 g to 5 kg per hectare of agricultural and/or horticultural crops.
  • Examples of application methods for the compounds of the invention and compositions thereof, that is the methods of controlling pests in the agriculture are spraying, atomizing, dusting, brushing on, dressing, scattering or pouring which are to be selected to suit the intended aims of the prevailing circumstances.
  • the active ingredient can reach the plants via the root system (systemic action), by applying the compound to the locus of the plants, for example by application of a liquid composition of the compound into the soil (by drenching), or by applying a solid form of the compound in the form of granules to the soil (soil application).
  • systemic action by applying the compound to the locus of the plants, for example by application of a liquid composition of the compound into the soil (by drenching), or by applying a solid form of the compound in the form of granules to the soil (soil application).
  • granules can be metered into the flooded paddy-field.
  • the application of the compounds of the present invention to the soil is a preferred application method.
  • Typical rates of application per hectare is generally 1 to 2000 g of active ingredient per hectare, in particular 10 to 1000 g/ha, preferably 10 to 600 g/ha, such as 50 to 300 g/ha.
  • the present invention provides a seed comprising compound of formula (I) and/or stereoisomers, agriculturally acceptable salts, tautomers, N-oxides thereof or composition or combination thereof, wherein the amount of the compound of the formula (I) or an N-oxide or an agriculturally acceptable salt thereof is ranging from 0.1 g to 10 kg per 100 kg of seed.
  • the compounds of the invention and compositions thereof are also suitable for the protection of plant propagation material, for example seeds, such as fruit, tubers or kernels, or nursery plants, against pests of the abovementioned type.
  • the propagation material can be treated with the compound prior to planting, for example seed can be treated prior to sowing.
  • the compound can be applied to seed kernels (coating), either by soaking the kernels in a liquid composition or by applying a layer of a solid composition. It is also possible to apply the compositions when the propagation material is planted to the site of application, for example into the seed furrow during drilling.
  • Typical treatment rates would depend on the plant and nematodes to be controlled and are generally between 1 to 200 grams per 100 kg of seeds, preferably between 5 to 150 grams per 100 kg of seeds, such as between 10 to 100 grams per 100 kg of seeds.
  • the application of the compounds of the present invention to seeds is a preferred application method.
  • seed embraces seeds and plant propagules of all kinds including but not limited to true seeds, seed pieces, suckers, corns, bulbs, fruit, tubers, grains, rhizomes, cuttings, cut shoots and the like and means in a preferred embodiment true seeds.
  • the present invention also comprises seeds coated or treated with or containing a compound of formula I.
  • coated or treated with and/or containing generally signifies that the active ingredient is for the most part on the surface of the seed at the time of application, although a greater or lesser part of the ingredient may penetrate into the seed material, depending on the method of application.
  • the present invention makes available a plant propagation material adhered thereto with a compound of formula (I).
  • a composition comprising a plant propagation material treated with a compound of formula (I).
  • Seed treatment comprises all suitable seed treatment techniques known in the art, such as seed dressing, seed coating, seed dusting, seed soaking and seed pelleting.
  • the seed treatment application of the compound formula I can be carried out by any known methods, such as spraying or by dusting the seeds before sowing or during the sowing/planting of the seeds.
  • Suitable target plants are, in particular, cereals, such as wheat, barley, rye, oats, rice, maize or sorghum; beet, such as sugar or fodder beet; fruit, for example banana, pomaceous fruit, stone fruit or soft fruit, such as apples, pears, plums, peaches, almonds, cherries or berries, for example strawberries, raspberries or blackberries; leguminous plants, such as beans, lentils, peas or soya; oil plants, such as oilseed rape, mustard, poppies, olives, sunflowers, coconut, castor, cocoa or ground nuts; cucurbits, such as pumpkins, cucumbers or melons; fibre plants, such as cotton, flax, hemp or jute; citrus fruit, such as oranges, lemons, grapefruit or
  • the plant is selected from cereals, corn, soybean, rice, sugarcane, vegetables and oil plants.
  • plant is to be understood as including also plants which have been so transformed by the use of recombinant DNA techniques that they are capable of synthesizing one or more selectively acting toxins, such as are known, for example, from toxin-producing bacteria, especially those of the genus Bacillus and also plants which have been selected or hybridized to preserve and / or attain a desired trait, such as insect, fungi and /or nematode resistance.
  • Toxins that can be expressed by such transgenic plants include, for example, insecticidal proteins from Bacillus cereus or Bacillus popilliae; or insecticidal proteins from Bacillus thuringiensis, such as 8-endotoxins, e.g. Cry1Ab, Cry1Ac, Cry1F, Cry1Fa2, Cry2Ab, Cry3A, Cry3Bb1 or Cry9C, or vegetative insecticidal proteins (Vip), e.g. Vip1, Vip2, Vip3 or Vip3A; or insecticidal proteins of bacteria colonising nematodes, for example Photorhabdus spp.
  • insecticidal proteins from Bacillus cereus or Bacillus popilliae such as 8-endotoxins, e.g. Cry1Ab, Cry1Ac, Cry1F, Cry1Fa2, Cry2Ab, Cry3A, Cry3Bb1 or Cry9C, or vegetative insect
  • Xenorhabdus spp. such as Photorhabdus luminescens, Xenorhabdus nematophilus
  • toxins produced by animals such as scorpion toxins, arachnid toxins, wasp toxins and other insect-specific neurotoxins
  • toxins produced by fungi such as Streptomycetes toxins, plant lectins, such as pea lectins, barley lectins or snowdrop lectins
  • agglutinins proteinase inhibitors, such as trypsin inhibitors, serine protease inhibitors, patatin, cystatin, papain inhibitors
  • ribosome- inactivating proteins (RIP) such as ricin, maize-RIP, abrin, luffin, saporin or bryodin
  • steroid metabolism enzymes such as 3-hydroxysteroidoxidase, ecdysteroid-UDP-glycosyl- transferase, cholesterol oxidases, ecdy
  • 8-endotoxins for example Cry1Ab, Cry1Ac, Cry1F, Cry1Fa2, Cry2Ab, Cry3A, Cry3Bb1 or Cry9C, or vegetative insecticidal proteins (Vip), for example Vip1, Vip2, Vip3 or Vip3A
  • Vip vegetative insecticidal proteins
  • Hybrid toxins are produced recombinantly by a new combination of different domains of those proteins (see, for example, WO 02/15701).
  • Truncated toxins for example a truncated Cry1Ab, are known.
  • modified toxins one or more amino acids of the naturally occurring toxin are replaced.
  • preferably non-naturally present protease recognition sequences are inserted into the toxin, such as, for example, in the case of Cry3A055, a cathepsin-G- recognition sequence is inserted into a Cry3A toxin (see WO 03/018810).
  • Examples of such toxins or transgenic plants capable of synthesising such toxins are disclosed, for example, in EP-A-0 374 753, WO 93/07278, WO 95/34656, EP-A-0427529, EP-A-451878 and WO 03/052073.
  • transgenic plants are generally known to the person skilled in the art and are described, for example, in the publications mentioned above.
  • Cryl-type deoxyribonucleic acids and their preparation are known, for example, from WO 95/34656, EP-A-0367474, EP-A-0401979 and WO 90/13651.
  • the toxin contained in the transgenic plants imparts to the plants tolerance to harmful insects.
  • insects can occur in any taxonomic group of insects, but are especially commonly found in the beetles (Coleoptera), two-winged insects (Diptera) and butterflies (Lepidoptera).
  • Coldhousea two-winged insects
  • butterflies Lepidoptera
  • Transgenic plants containing one or more genes that code for an insecticidal resistance and express one or more toxins are known and some of them are commercially available.
  • YieldGard® (maize variety that expresses a Cry1Ab toxin); YieldGard Rootworm® (maize variety that expresses a Cry3Bb1 toxin); YieldGard Plus® (maize variety that expresses a Cry1Ab and a Cry3Bb1 toxin); Starlink® (maize variety that expresses a Cry9C toxin); HerculexI® (maize variety that expresses a Cry1Fa2 toxin and the enzyme phosphinothricine N-acetyltransferase(PAT) to achieve tolerance to the herbicide glufosinate ammonium); NuCOTN 33B® (cotton variety that expresses a Cry1Ac toxin); Bollgard I® (cotton variety that expresses a Cry1Ac toxin); Bollgard II® (cotton variety that expresses a Cry1Ac and a C
  • transgenic plants are: i) Bt11 Maize from Syngenta Seeds SAS, Chemin de l'Hobit 27, F-31790 St. Sauveur, France, registration number C/FR/96/05/10. Genetically modified Zea mays which has been rendered resistant to attack by the European corn borer (Ostrinia nubi/alis and Sesamia nonagrioides) by transgenic expression of a truncated Cry1Ab toxin. Bt11 maize also transgenically expresses the enzyme PAT to achieve tolerance to the herbicide glufosinate ammonium; ii)Bt176 Maize from Syngenta Seeds SAS, Chemin de l'Hobit 27, F-31790 St.
  • This toxin is Cry3A055 modified by insertion of a cathepsin-G-protease recognition sequence.
  • the preparation of such transgenic maize plants is described in WO 03/018810; iv)MON 863 Maize from Monsanto Europe S.A. 270-272 Avenue de Tervuren, B-1150 Brussels, Belgium, registration number C/DE/02/9.
  • MON 863 expresses a Cry3Bb1 toxin and has resistance to certain Coleoptera insects; v) IPC 531 Cotton from Monsanto Europe S.A.
  • NK603 x MON 810 Maize transgenically expresses the protein CP4 EPSPS, obtained from Agrobacterium sp. strain CP4, which imparts tolerance to the herbicide Roundup® (contains glyphosate), and also a Cry1Ab toxin obtained from Bacillus thuringiensis subsp. kurstaki which brings about tolerance to certain Lepidoptera, include the European corn borer.
  • the present invention provides a combination comprising the compound of general formula (I), stereoisomer, agriculturally acceptable salts, tautomers or N-oxides thereof and one or more active compatible compound selected from fungicides, insecticides, nematicides, acaricides, biopesticides, herbicides, plant growth regulators, antibiotics, nutrients or fertilizers.
  • Compounds of this invention are effective for controlling nematodes and/or fungal pathogens of agronomic plants, both growing and harvested, when employed alone, they may also be used in combination with other biological active agents used in agriculture, such as one or more nematocides, insecticides, acaricides, fungicides, bactericides, plant activator, molluscicide, and pheromones (whether chemical or biological). Mixing the compounds of the invention or the compositions thereof in the use form as pesticides with other pesticides frequently results in a broader pesticidal spectrum of action.
  • the formula (I) compounds of this invention may be used effectively in conjunction or combination with pyrethroids, neonicotinoids, macrolides, diamides, phosphates, carbamates, cyclodienes, formamidines, phenol tin compounds, chlorinated hydrocarbons, benzoylphenyl ureas, pyrroles and the like.
  • the activity of the compositions according to the invention can be broadened considerably, and adapted to prevailing circumstances, by adding, for example, one or more insecticidally, acaricidally, nematicidally and/or fungicidally active agents.
  • the combinations compounds of formula (I) with other insecticidally, acaricidally, nematicidally and/or fungicidally active agents may also have further surprising advantages. For example, better tolerance by plants, reduced phytotoxicity, pests or fungi can be controlled in their different development stages or better behavior during their production, for example during grinding or mixing, during their storage or during their use.
  • the known and reported active compounds such as fungicides, insecticides, nematicides, acaricides, biopesticides, herbicides, safeners, plant growth regulators, antibiotics, fertilizers and nutrients can be combined with at least one compound of formula I of the present invention.
  • fungicides insecticides, nematicides, acaricides, biopesticides, herbicides, safeners, plant growth regulators, antibiotics, fertilizers and nutrients disclosed and reported in WO2017076739 (A to O) can be combined with compound of Formula I of the present invention.
  • the present invention also relates to such combinations comprising the compound of the present invention and active compatible compounds reported in WO2017076739.
  • the compounds of formula (I) of the present invention can also be combined with other insecticidal active compounds of unknown or uncertain mode of action: afidopyropen, afoxolaner, azadirachtin, amidoflumet, benzoximate, bifenazate, broflanilide, bromopropylate, chinomethionat, cryolite, dicloromezotiaz, dicofol, flufenerim, flometoquin, fluensulfone, fluhexafon, fluopyram, flupyradifurone, fluralaner, metoxadiazone, piperonyl butoxide, pyflubumide, pyridalyl, pyrifluquinazon, sulfoxaflor, tioxazafen, triflumezopyrim, 11-(4-chloro-2,6-dimethylphenyl)-12- hydroxy-1,4-dioxa-9-aza
  • the mass ratio of any two ingredients in each combination is selected as to give the desired effect, for example, enhanced activity. In general, the mass ratio would vary depending on the specific ingredient and how many ingredients are present in the combination. Generally, the mass ratio between any two ingredients in any combination of the present invention, independently of one another, is from 100:1 to 1:100, including from 99:1, 98:2, 97:3, 96:4, 95:5, 94:6, 93:7, 92:8, 91:9, 90:10, 89:11, 88:12, 87:13, 86:14, 85:15, 84:16, 83:17, 82:18, 81:19, 80:20, 79:21, 78:22, 77:23, 76:24, 75:25, 74:26, 73:27, 72:28, 71:29, 70:30, 69:31, 68:32, 67:33, 66:34, 65:45, 64:46, 63:47, 62:48
  • Preferred mass ratios between any two components of present invention are from 75:1 to 1:75, more preferably, 50:1 to 1.50, especially 25:1 to 1:25, advantageously 10:1 to 1:10, such as 5:1 to 1:5, for example 1:3 to 3:1.
  • the mixing ratios are understood to include, on the one hand, ratios by mass and also, on other hand, molar ratios.
  • the combinations of the present invention i.e. those comprising a compound of the present invention and one or more other biological active agents
  • ingredients of the combinations may be applied as a composition containing the combination, in which case (A) the compound of formula (I) and the one or more other ingredients in the combinations can be obtained from separate formulation sources and mixed together (known as a tank-mix, ready-to-apply, spray broth, or slurry), or (B) the compound of formula (I) and the one or more other ingredients can be obtained as single formulation mixture source (known as a pre-mix, ready-mix, concentrate, or formulated product).
  • A the compound of formula (I) and the one or more other ingredients in the combinations can be obtained from separate formulation sources and mixed together (known as a tank-mix, ready-to-apply, spray broth, or slurry), or
  • B) the compound of formula (I) and the one or more other ingredients can be obtained as single formulation mixture source (known as a pre-mix, ready-mix, concentrate, or formulated product).
  • a compound according to the present invention is applied as a combination.
  • the present invention also provides a composition comprising a compound according to the invention as herein described and one or more other biological active agents, and optionally one or more customary formulation auxiliaries; which may be in the form of a tank-mix or pre-mix composition.
  • the compounds of formula (I) are particularly useful for controlling and preventing helminth and nematode endo and ecto-parasitic infestations and infections in warm-blooded animals such as cattle, sheep, swine, camels, deer, horses, poultry, fish, rabbits, goats, mink, fox, chinchillas, dogs and cats as well as humans.
  • compounds of invention are especially useful for the control of helminths and nematodes.
  • helminths are members of the class Trematoda, commonly known as flukes or flatworms, especially members of the genera Fasciola, Fascioloides, Paramphistomu, Dicrocoelium, Eurytrema, Ophisthorchis, Fasciolopsis, Echinostoma and Paragonimus.
  • Nematodes which can be controlled by the formula (I) compounds include the genera Haemonchus, Ostertagia, Cooperia, Oesphagastomu, Nematodirus, Dictyocaulus, Trichuris, Dirofilaria, Ancyclostoma, Ascaria and the like.
  • the compounds of the 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 invention may be administered to the animals in their drinking water.
  • the dosage form chosen should provide the animal with about 0.01 mg/kg to 100 g/kg of animal body weight per day of the compound of the invention.
  • the compounds of the invention may be administered to animals parenterally, for example, by intraruminal, intramuscular, intravenous or subcutaneous injection.
  • the compounds of the invention may be dispersed or dissolved in a physiologically acceptable carrier for subcutaneous injection.
  • the compounds of the invention may be formulated into an implant for subcutaneous administration.
  • the compounds of the invention may be transdermally administered to animals.
  • the dosage form chosen should provide the animal with about 0.01 mg/kg to 100 mg/kg of animal body weight per day of the compound of the invention.
  • the compounds of the invention may also be applied topically to the animals in the form of dips, dusts, powders, collars, medallions, sprays and pour-on formulations.
  • dips and sprays usually contain about 0.5 ppm to 5,000 ppm and preferably about 1 ppm to 3,000 ppm of the compound of the invention.
  • the compounds of the invention may be formulated as ear tags for animals, particularly quadrupeds such as cattle and sheep.
  • a compound of formula (I) is an anti- helminth compound.
  • a compound of formula (I) is a pesticidal compound, preferably a nematicidal compound.
  • the compounds of the present invention not only control nematode pests effectively but also show positive crop response such as plant growth enhancement effects like enhanced crop vigor, enhanced root growth, enhanced tolerance to drought, high salt, high temperature, chill, frost or light radiation, improved flowering, efficient water & nutrient utilization (such as improved nitrogen assimilation), enhanced quality plant product, more number of productive tillers, enhanced resistance to fungi, insects, pests and the like, which results in higher yields.
  • plant growth enhancement effects like enhanced crop vigor, enhanced root growth, enhanced tolerance to drought, high salt, high temperature, chill, frost or light radiation, improved flowering, efficient water & nutrient utilization (such as improved nitrogen assimilation), enhanced quality plant product, more number of productive tillers, enhanced resistance to fungi, insects, pests and the like, which results in higher yields.
  • Example 1 Preparation of 4,4-difluorobut-3-en-1-yl 2-(4-chloro-1H-pyrazol-1-yl)acetate To a solution of 2-(4-chloro-1H-pyrazol-1-yl)acetic acid (250 mg, 1.56 mmol) in dry N,N- dimethylformamide (8 mL), N,N-diisopropylethylamine (0.27 ml, 1.56 mmol) and 4-bromo-1,1- difluorobut-1-ene (532 mg, 3.11 mmol) were added, and the reaction mixture was stirred at 80 °C for 16 h.
  • the reaction mixture was diluted with ethyl acetate (30 mL) and water (30 mL), the organic layer was separated, and the aqueous layer was extracted again with ethyl acetate (30 mL). The combined organic layers were dried over anhydrous sodium sulphate, filtered and concentrated under reduced pressure to obtain a crude product.
  • the reaction mixture was diluted with ethyl acetate (30 mL) and water (30 mL), the organic layer was separated and the aqueous layer was extracted again with ethyl acetate (30 mL). The combined organic layers were dried over anhydrous sodium sulphate, filtered and concentrated under reduced pressure to obtain a crude product.
  • the reaction mixture was diluted with ethyl acetate (30 mL) and water (30 mL), the organic layer was separated and the aqueous layer was extracted again with ethyl acetate (30 mL). The combined organic layers were dried over anhydrous sodium sulphate, filtered and concentrated under reduced pressure to obtain a crude product.
  • reaction mixture was concentrated, diluted with water (5 ml) and washed with ethyl acetate.
  • the aqeoues layer was acidified with conc. hydrochloric acid and extracted with ethyl acetate (60ml x 2).
  • the reaction mixture was diluted with ethyl acetate (30 mL) and water (30 mL), the organic layer was separated and the aqueous layer was extracted again with ethyl acetate (30 mL). The combined organic layers were dried over anhydrous sodium sulphate, filtered and concentrated under reduced pressure to obtain a crude product.
  • the reaction mixture was diluted with ethyl acetate (30 mL) and water (30 mL), the organic layer was separated and the aqueous layer was extracted again with ethyl acetate (30 mL). The combined organic layers were dried over anhydrous sodium sulphate, filtered and concentrated under reduced pressure to obtain a crude product.
  • the reaction mixture was diluted with ethyl acetate (30 mL) and water (30 mL), the organic layer was separated and the aqueous layer was extracted again with ethyl acetate (30 mL). The combined organic layer was dried over anhydrous sodium sulphate, filtered and concentrated under reduced pressure to obtain a crude product.
  • the reaction mixture was diluted with ethyl acetate (30 mL) and water (30 mL), the organic layer was separated and the aqueous layer was extracted again with ethyl acetate (30 mL). The combined organic layers were dried over anhydrous sodium sulphate, filtered and concentrated under reduced pressure to obtain a crude product.
  • the reaction mixture was diluted with ethyl acetate (30 mL) and water (30 mL), the organic layer was separated and the aqueous layer was extracted again with ethyl acetate (30 mL). The combined organic layers were dried over anhydrous sodium sulphate, filtered and concentrated under reduced pressure to obtain a crude product.
  • the reaction mixture was diluted with ethyl acetate (30 mL) and water (30 mL), the organic layer was separated and the aqueous layer was extracted again with ethyl acetate (30 mL). The combined organic layers were dried over anhydrous sodium sulphate, filtered and concentrated under reduced pressure to obtain a crude product.
  • the reaction mixture was diluted with ethyl acetate (30 mL) and water (30 mL), the organic layer was separated and the aqueous layer was extracted again with ethyl acetate (30 mL). The combined organic layers were dried over anhydrous sodium sulphate, filtered and concentrated under reduced pressure to obtain a crude product.
  • the reaction mixture was diluted with ethyl acetate (30 mL) and water (30 mL), the organic layer was separated and the aqueous layer was extracted again with ethyl acetate (30 mL). The combined organic layers were dried over anhydrous sodium sulphate, filtered and concentrated under reduced pressure to obtain a crude product.
  • Step 2 Preparation of 2-(3-methyl-1H-indazol-1-yl)acetic acid To a solution of ethyl 2-(3-methyl-1H-indazol-1-yl)acetate (590 mg, 2.70 mmol) in methanol- tetrahydrofuran (4 ml:2 ml), lithium hydroxide (129 mg, 5.41 mmol) in water (0.5 ml) was added, and the resulting mixture was stirred at room temperature for 2 h.
  • the reaction mixture was diluted with ethyl acetate (30 mL) and water (30 mL), the organic layer was separated and the aqueous layer was extracted again with ethyl acetate (30 mL). The combined organic layers were dried over anhydrous sodium sulphate, filtered and concentrated under reduced pressure to obtain a crude product.
  • the reaction mixture was diluted with ethyl acetate (30 mL) and water (30 mL), the organic layer was separated and the aqueous layer was extracted again with ethyl acetate (30 mL). The combined organic layers were dried over anhydrous sodium sulphate, filtered and concentrated under reduced pressure to obtain a crude product, tert-butyl 2-(4,5-dichloro-1H-imidazol-1-yl)acetate (1.8 g, 7.17 mmol, 98 % yield).
  • the reaction mixture was diluted with ethyl acetate (30 mL) and water (30 mL), the organic layer was separated and the aqueous layer was extracted again with ethyl acetate (30 mL). The combined organic layers were dried over anhydrous sodium sulphate, filtered and concentrated under reduced pressure to obtain a crude product.
  • the reaction mixture was diluted with ethyl acetate (30 mL) and water (30 mL), the organic layer was separated and the aqueous layer was extracted again with ethyl acetate (30 mL). The combined organic layers were dried over anhydrous sodium sulphate, filtered and concentrated under reduced pressure to obtain a crude product.
  • Example 1 Meloidogyne incognita (Root-knot nematode): IN VITRO TEST Meloidogyne incognita: The test compounds, at a concentration of 300 ppm, were pipetted into the wells of a 24-well microtiter plate containing, per well, 500 ⁇ L of distilled water with 50 Meloidogyne incognita juveniles. The suspension was lightly shaken for uniform mixing of compounds. The test plates were covered with lids, and were incubated at 25 °C temperature and 90% RH.
  • Dead/inactive nematodes were counted at an interval of 48, 72 and 96 hours under a microscope and the percent mortality was calculated by comparing the result of the treatment with the one of the untreated control.
  • Compounds 8 17 25 35 36 37 44 47 55 56 57 58 61 62 63 64 65 66 67 68 69 70 74 75 at 300ppm showed more than 70% mortality in the tests, where there was no mortality in the untreated check.
  • Meloidogyne incognita IN VIVO TEST Cucumber plants were grown in seedling trays containing a mixture of Sand:Soil:FYM:Cocopeat in ratio of 1:1:1:1.
  • test compounds One mL of test compounds at the desired test concentrations was applied into the soil with the help of a micropipette when the cucumber seedlings were ten days old. After the application the seedlings were inoculated with approximately 2000 freshly hatched second-stage juveniles of Meloidogyne incognita. The treated plants were allowed to grow at 27 °C temperature under greenhouse conditions. Observation of gall rating was recorded 15 days after the application. Plants were carefully uprooted and roots were washed thoroughly.

Abstract

The present invention relates to novel N-linker heterocyclic fluoroalkenyl compounds of formula (I), Formula (I) wherein, R1, R2, R3, ring A and Y are as defined in the detailed description. The present invention further relates to their preparation and their use to protect crops against undesired phytopathogenic microorganisms, e.g. against phytopathogenic fungi and pests such as nematodes.

Description

NEMATOCIDAL COMPOUNDS AND USE THEREOF FIELD OF THE INVENTION The present invention relates to novel nematicidal compounds. More particularly, the present invention relates to a N-linked heterocyclic fluoroalkenyl compounds of formula (I) and to a process for the preparation thereof. The present invention further relates to the use of the compounds of formula (I) as crop protection agents for the control of pests such as plant parasitic nematodes. BACKGROUND OF THE INVENTION WO2019186498, WO2020075107, WO2003042153 and WO9708130 disclose fluoroalkenyl heterocyclic compounds showing nematicidal activity, wherein heterocycles containing heteroatoms such as nitrogen, sulfur and oxygen are attached through a C-linker to fluoroalkenyl groups. Further WO2020157668 disclose caffeine or theophylline derivatives having nematicidal activity. The control of damages to crops caused by phytopathogenic microorganisms and pests is extremely important for achieving high crop efficiency. For instance, damage caused by plant diseases to ornamental, vegetable, field, cereal and fruit crops can lead tosignificant reduction in productivity and thereby result in increased cost for the consumer. Even if many products are commercially available to control such damage, the need continues for new compounds which are more effective, less costly, less toxic, environmentally safer and/or have different modes of action. The effectiveness of the diflurobutenes, trifluorobutenes and other compounds described in the prior art is not fully satisfactory in various aspects as efficacy, treatment cost under practical conditions and plant compatibility etc. Therefore, it is always of high interest in agriculture to find novel pesticidal compounds in order to avoid and/or control the development of microorganisms such as fungal or bacterial pathogens or pests being resistant to known active ingredients under more advantadgeous conditions.. It is therefore specifically of high interest to use novel compounds being more active than those already known, with the aim of decreasing the amounts of active compounds to be used, whilst at the same time maintaining an effectiveness and long lasting activity at least in an equivalent way compared to the already known compounds. The present invention describes compounds of formula (I) which possess the above mentioned effects or advantages. Such compounds of formula (I), namely N-linked heterocyclic fluoroalkenyl compounds wherein the heterocyclic ring is substituted according to the invention, show unexpected and significantly higher activity against undesired pests such as phytoparasitic nematodes SUMMARY OF THE INVENTION The present invention provides a novel N-linked heterocyclic fluoroalkenyl compoundof formula (I),
Figure imgf000003_0001
Formula (I) wherein, R1, R2, R3, ring A and Y are as defined in the detailed description. In one embodiment, the present invention provides a process for the preparation of compounds of formula (I). In another embodiment, the present invention provides a use of the compounds of formula (I) as crop protection agent for the control of phytoparasitic organisms, especially of plant parasitic nematodes. DEFINITIONS The terminologies used in the present disclosure are for illustrative purpose only and in no manner limit the scope of the present invention disclosed in the present disclosure. As used herein, the terms “comprises”, “comprising”, “includes”, “including”, “has”, “having”, “contains”, “containing”, “characterized by” or any other variation thereof, are intended to cover a non-exclusive inclusion, subject to any limitation explicitly indicated. For example, a composition, mixture, process or method that comprises a list of elements is not necessarily limited to only those elements but may include other elements not expressly listed or inherent to such composition, mixture, process or method. The 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 “consisting essentially of” occupies a middle ground between “comprising” and “consisting of”. Further, unless expressly stated to the contrary, “or” refers to an inclusive “or” and not to an exclusive “or”. For example, a condition A “or” B is satisfied by any one of the following: A is true (or present) and B is false (or not present), A is false (or not present) and B is true (or present), and both A and B are true (or present). Also, the indefinite articles “a” and “an” preceding an element or component of the present invention are intended to be nonrestrictive regarding the number of instances (i.e. occurrences) of the element or component. Therefore “a” or “an” should be read to include one or at least one, and the singular word form of the element or component also includes the plural unless the number is obviously meant to be singular. As referred to in this disclosure, the term “pesticide” in each case also always comprises the term “crop protection agent”. The term “invertebrate pest” includes arthropods, gastropods and nematodes of economic importance as pests. The term “arthropod” includes insects, mites, spiders, scorpions, centipedes, millipedes, pill bugs and symphylans. The term “gastropod” includes snails, slugs and other Stylommatophora. The term “nematode” refers to a living organism of the Phylum Nematoda. The term “helminths” includes roundworms, heartworms, phytophagous nematodes (Nematoda), flukes (Trematoda), acanthocephala and tapeworms (Cestoda). The term “undesired microorganisms” or “phytopathogenic microorganisms” such as fungal or bacterial pathogens includes Plasmodiophoromycetes, Oomycetes, Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes and Deuteromycetes and Pseudomonadaceae, Rhizobiaceae, Enterobacteriaceae, Corynebacteriaceae and Streptomycetaceae respectively. In the context of this disclosure “invertebrate pest control” means inhibition of invertebrate pest development (including mortality, feeding reduction, and/or mating disruption), and related expressions are defined analogously. The term “agronomic” refers to the production of field crops such as for food and fiber and includes the growth of corn, soybeans and other legumes, rice, cereal (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 fruit (berries, cherries) and other specialty crops (e.g., canola, sunflower, olives). The term “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. biologically effective) amount of a compound of the present invention, typically in the form of a composition formulated for veterinary use, to the animal to be protected. As referred to in the present disclosure and claims, 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 necrosis, 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 skilled in the art will appreciate that 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). Additionally, the person skilled in the art knows processes or methods or technology to separate, enrich, and/or to selectively prepare said isomers. The meaning of various terms used in the description shall now be illustrated: In the above description, the term “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 C1 to C15 alkyl, preferably C1 to C10 alkyl, more preferably C1 to C6 alkyl. Non limiting examples of 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 1-ethyl-2-methylpropyl or the different isomers. If 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, may be mono- or polysubstituted identically or differently and independently by alkyl. The same also applies to composite substituents in which other radicals, for example alkenyl, alkynyl, hydroxyl, halogen, carbonyl, carbonyloxy and the like, are at the end. The term “alkenyl”, used either alone or in compound words includes straight-chain or branched C2 to C15 alkenes, preferably C2 to C10 alkenes, more preferably C2 to C6 alkenes. Non limiting 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, 1-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, 1- methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, 1-methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl, 1,1-dimethyl-2-propenyl, 1,2-dimethyl-1-propenyl, 1,2-dimethyl-2 -propenyl, 1- ethyl-1-propenyl, 1-ethyl-2-propenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl, 1- methyl-1-pentenyl, 2-methyl-1-pentenyl, 3-methyl-1-pentenyl, 4-methyl-1-pentenyl, 1-methyl-2- pentenyl, 2-methyl-2-pentenyl, 3-methyl-2-pentenyl, 4-methyl-2-pentenyl, 1-methyl-3-pentenyl, 2- methyl-3-pentenyl, 3-methyl-3-pentenyl, 4-methyl-3-pentenyl, 1-methyl-4-pentenyl, 2-methyl-4- pentenyl, 3-methyl-4-pentenyl, 4-methyl-4-pentenyl, 1,1-dimethyl-2-butenyl, 1,1-dimethyl-3-butenyl, 1,2-dimethyl-1-butenyl, 1,2-dimethyl-2-butenyl, 1,2-dimethyl-3-butenyl, 1,3-dimethyl-1-butenyl, l,3- dimethyl-2-butenyl, l,3-dimethyl-3-butenyl, 2,2-dimethyl-3-butenyl, 2,3-dimethyl-1-butenyl, 2,3- dimethyl-2-butenyl, 2,3-dimethyl-3-butenyl, 3,3-dimethyl-1-butenyl, 3,3-dimethyl-2-butenyl, 1-ethyl- 1-butenyl, 1-ethyl-2-butenyl, 1-ethyl-3-butenyl, 2-ethyl- 1-butenyl, 2-ethyl-2-butenyl, 2-ethyl-3- butenyl, 1,1,2-trimethyl-2-propenyl, 1-ethyl-1-methyl-2-propenyl, 1-ethyl-2-methyl-1-propenyl and 1- ethyl-2-methyl-2-propenyl and the different isomers. The term “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. The term “alkynyl”, used either alone or in compound words includes branched or straight-chain C2 to C24 alkynes, preferably C2 to C15 alkynes, more preferably C2 to C10 alkynes, most preferably C2 to C6 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-pentynyl, 3-pentynyl, 4-pentynyl, 1-methyl-2- butynyl, 1-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, 1- methyl-3-pentynyl, 1-methyl-4-pentynyl, 2-methyl-3-pentynyl, 2-methyl-4-pentynyl, 3-methyl-1- pentynyl, 3-methyl-4-pentynyl, 4-methyl-1-pentynyl, 4-methyl-2-pentynyl, 1,1-dimethyl-2-butynyl, 1,1-dimethyl-3-butynyl, 1,2-dimethyl-3-butynyl, 2,2-dimethyl-3-butynyl, 3,3-dimethyl-1-butynyl, 1- ethyl-2-butynyl, 1-ethyl-3-butynyl, 2-ethyl-3-butynyl and 1-ethyl-1-methyl-2-propynyl and the different isomers. This definition also applies to alkynyl as a part of a composite substituent, for example haloalkynyl etc., unless specifically defined elsewhere. The term “Alkynyl” can also include moieties comprised of multiple triple bonds such as 2,5-hexadiynyl. The term “cyclic alkyl” or “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. The term “cycloalkenyl” means alkenyl closed to form a ring including monocyclic, partially unsaturated hydrocarbyl groups. Non limiting examples include but are not limited to cyclopentenyl and cyclohexenyl. This definition also applies to cycloalkenyl as a part of a composite substituent, for example cycloalkenylalkyl etc., unless specifically defined elsewhere. The term “cycloalkynyl” means alkynyl closed to form a ring including monocyclic, partially unsaturated groups. This definition also applies to cycloalkynyl as a part of a composite substituent, for example cycloalkynylalkyl etc., unless specifically defined elsewhere. The term “cycloalkoxy”, “cycloalkenyloxy” and the like are defined analogously. Non limiting examples of cycloalkoxy include cyclopropyloxy, cyclopentyloxy and cyclohexyloxy. This definition also applies to cycloalkoxy as a part of a composite substituent, for example cycloalkoxy alkyl etc., unless specifically defined elsewhere. The term “alkoxy” used either alone or in compound words included C1 to C15 alkoxy, preferably C1 to C10 alkoxy, more preferably C1 to C6 alkoxy. Examples of alkoxy 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 1-ethyl-2-methylpropoxy and the different isomers. This definition also applies to alkoxy as a part of a composite substituent, for example haloalkoxy, alkynylalkoxy, etc., unless specifically defined elsewhere. The term “alkylthio” includes branched or straight-chain alkylthio moieties such as methylthio, ethylthio, propylthio, 1-methylethylthio, butylthio, 1-methylpropylthio, 2-methylpropylthio, 1,1- dimethylethylthio, pentylthio, 1-methylbutylthio, 2-methylbutylthio, 3-methylbutylthio, 2,2- dimethylpropylthio, 1-ethylpropylthio, hexylthio, 1,1-dimethylpropylthio, 1,2-dimethylpropylthio, 1- methylpentylthio, 2-methylpentylthio, 3-methylpentylthio, 4-methylpentylthio, 1,1-dimethylbutylthio, 1,2-dimethylbutylthio, 1,3-dimethylbutylthio, 2,2-dimethylbutylthio, 2,3-dimethylbutylthio, 3,3- dimethylbutylthio, 1-ethylbutylthio, 2-ethylbutylthio, 1,1,2-trimethylpropylthio, 1,2,2- trimethylpropylthio, 1-ethyl-1-methylpropylthio and 1-ethyl-2-methylpropylthio and the different isomers. 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. The term “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. Non-limiting examples of “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. This definition also applies to haloalkyl as a part of a composite substituent, for example haloalkylaminoalkyl etc., unless specifically defined elsewhere. The terms “haloalkenyl” and “haloalkynyl” are defined analogously except that, instead of alkyl groups, alkenyl and alkynyl groups are present as a part of the substituent. The term “haloalkoxy” means straight-chain or branched alkoxy groups where some or all of the hydrogen atoms in these groups may be replaced by halogen atoms as specified above. Non-limiting examples of haloalkoxy include chloromethoxy, bromomethoxy, dichloromethoxy, trichloromethoxy, fluoromethoxy, difluoromethoxy, trifluoromethoxy, chlorofluoromethoxy, dichlorofluoromethoxy, chlorodifluoromethoxy, 1-chloroethoxy, 1-bromoethoxy, 1-fluoroethoxy, 2-fluoroethoxy, 2,2- difluoroethoxy, 2,2,2-trifluoroethoxy, 2-chloro-2-fluoroethoxy, 2-chloro-2,2-difluoroethoxy, 2,2- dichloro-2-fluoroethoxy, 2,2,2-trichloroethoxy, pentafluoroethoxy and 1,1,1-trifluoroprop-2-oxy. This definition also applies to haloalkoxy as a part of a composite substituent, for example haloalkoxyalkyl etc., unless specifically defined elsewhere. The terms “haloalkylthio” or “haloalkylsulfanyl” means straight-chain or branched alkylthio groups where some or all of the hydrogen atoms in these groups may be replaced by halogen atoms as specified above. Non-limiting examples of haloalkylthio include chloromethylthio, bromomethylthio, dichloromethylthio, trichloromethylthio, fluoromethylthio, difluoromethylthio, trifluoromethylthio, chlorofluoromethylthio, dichlorofluoromethylthio, chlorodifluoromethylthio, 1-chloroethylthio, 1- bromoethylthio, 1- fluoroethylthio, 2-fluoroethylthio, 2,2-difluoroethylthio, 2,2,2-trifluoroethylthio, 2- chloro-2- fluoroethylthio, 2-chloro-2,2-difluoroethylthio, 2,2-dichloro-2-fluoroethylthio, 2,2,2- trichloroethylthio, pentafluoroethylthio and 1,1,1-trifluoroprop-2-ylthio. This definition also applies to haloalkylthio as a part of a composite substituent, for example haloalkylthioalkyl etc., unless specifically defined elsewhere. Non limiting examples of “haloalkylsulfinyl” include CF3S(O), CCl3S(O), CF3CH2S(O) and CF3CF2S(O). Non limiting examples of “haloalkylsulfonyl” include CF3S(O)2, CCl3S(O)2, CF3CH2S(O)2 and CF3CF2S(O)2. Non limiting examples of “alkylsulfinyl” include but are not limited to methylsulphinyl, ethylsulphinyl, propylsulphinyl, 1-methylethylsulphinyl, butylsulphinyl, 1-methylpropylsulphinyl, 2- methylpropylsulphinyl, 1,1-dimethylethylsulphinyl, pentylsulphinyl, 1-methylbutylsulphinyl, 2- methylbutylsulphinyl, 3-methylbutylsulphinyl, 2,2-dimethylpropylsulphinyl, 1-ethylpropylsulphinyl, hexylsulphinyl, 1,1-dimethylpropylsulphinyl, 1,2-dimethylpropylsulphinyl, 1-methylpentylsulphinyl, 2-methylpentylsulphinyl, 3-methylpentylsulphinyl, 4-methylpentylsulphinyl, 1,1- dimethylbutylsulphinyl, 1,2-dimethylbutylsulphinyl, 1,3-dimethylbutylsulphinyl, 2,2- dimethylbutylsulphinyl, 2,3-dimethylbutylsulphinyl, 3,3-dimethylbutylsulphinyl, 1- ethylbutylsulphinyl, 2-ethylbutylsulphinyl, 1,1,2-trimethylpropylsulphinyl, 1,2,2- trimethylpropylsulphinyl, 1-ethyl-1-methylpropylsulphinyl and 1-ethyl-2-methylpropylsulphinyl and the different isomers. Non limiting examples of “alkylsulfonyl” include but are not limited to methylsulphonyl, ethylsulphonyl, propylsulphonyl, 1-methylethylsulphonyl, butylsulphonyl, 1-methylpropylsulphonyl, 2-methylpropylsulphonyl, 1,1-dimethylethylsulphonyl, pentylsulphonyl, 1-methylbutylsulphonyl, 2- methylbutylsulphonyl, 3-methylbutylsulphonyl, 2,2-dimethylpropylsulphonyl, 1- ethylpropylsulphonyl, hexylsulphonyl, 1,1-dimethylpropylsulphonyl, 1,2-dimethylpropylsulphonyl, 1- methylpentylsulphonyl, 2-methylpentylsulphonyl, 3-methylpentylsulphonyl, 4- methylpentylsulphonyl, 1,1-dimethylbutylsulphonyl, 1,2-dimethylbutylsulphonyl, 1,3- dimethylbutylsulphonyl, 2,2-dimethylbutylsulphonyl, 2,3-dimethylbutylsulphonyl, 3,3- dimethylbutylsulphonyl, 1-ethylbutylsulphonyl, 2-ethylbutylsulphonyl, 1,1,2- trimethylpropylsulphonyl, 1,2,2-trimethylpropylsulphonyl, 1-ethyl-1-methylpropylsulphonyl and 1- ethyl-2-methylpropylsulphonyl and the different isomers. The term “arylsulfonyl” includes Ar-S(O)2, wherein Ar can be any carbocyle or heterocylcle. This definition also applies to alkylsulphonyl as a part of a composite substituent, for example alkylsulphonylalkyl etc., unless defined elsewhere. The term “ring” or “ring system” as a component of formula I is carbocyclyl or heterocyclyl. The term “ring system” denotes one or more rings. The term “aromatic” indicates that the Hueckel rule is satisfied and the term “non-aromatic” indicates that the Hueckel rule is not satisfied. The terms “carbocycle” or “carbocyclic” or “carbocyclyl” include “aromatic carbocyclic ring system” and “nonaromatic carbocylic ring system” 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. The term “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. In addition, 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. The term “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. The terms “heterocyclyl” or “heterocyclic” includes “aromatic heterocycle” or “heteroaryl ring system” and “nonaromatic heterocycle ring system” or polycyclic or bicyclic (spiro, fused, bridged, non-fused) ring compounds in which ring may be aromatic or non-aromatic, wherein the heterocycle ring contains at least one heteroatom selected from N, O, S(O)0-2, and or C ring member of the heterocycle may be replaced by C(=O), C(=S), C(=CR*R*) and C=NR*, * indicates integers. The terms “non-aromatic heterocycle” or “non-aromatic heterocyclic” means three- to fifteen- membered, preferably three- to twelve-membered, saturated or partially unsaturated heterocycle containing one to four heteroatoms from the group of oxygen, nitrogen and sulphur: mono, bi- or tricyclic heterocycles which contain, in addition to 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, tetrahydrofuranyl, tetrahydrothienyl, pyrrolidinyl, isoxazolidinyl, isothiazolidinyl, pyrazolidinyl, oxazolidinyl, thiazolidinyl, imidazolidinyl, oxadiazolidinyl, thiadiazolidinyl, triazolidinyl, dihydrofuryl, dihydrothienyl, pyrrolinyl, isoxazolinyl, isothiazolinyl, dihydropyrazolyl, dihydrooxazolyl, dihydrothiazolyl, piperidinyl, pyrazynyl, morpholinyl, thiomorphlinyl, l,3-dioxany, tetrahydropyranyl, tetrahydrothienyl; wherein these rings are attached to the skeleton via one of the carbon or nitrogen of said rings. This definition also applies to heterocyclyl as a part of a composite substituent, for example heterocyclylalkyl etc., unless specifically defined elsewhere. The term "heteroaryl" or "aromatic heterocyclic" means 5 -membered, fully unsaturated monocyclic ring system containing one to four heteroatoms selected 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 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, thiazolyl, imidazolyl, oxadiazolyl, thiadiazolyl, triazolyl, tetrazolyl; wherein these rings are attached to the skeleton via one of the carbon or nitrogen of said rings, 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) pyridinyl, pyridazinyl, pyrimidinyl, pyrazinyl. This definition also applies to heteroaryl as a part of a composite substituent, for example heteroarylalkyl etc., unless specifically defined elsewhere. The term “amide” means A-R'C=ONR''-B, wherein R' and R'' indicates substituents and A and B indicate any group. The term “thioamide” means A-R'C=SNR''-B, wherein R' and R'' indicates substituents and A and B indicate any group. The total number of carbon atoms in a substituent group is indicated by the “Ci-Cj” prefix where i and j are numbers from 1 to 21. For example, C1-C3 alkoxy designates methoxy through propoxy. In the above recitations, when a compound of formula (I) is comprised of one or more heterocyclic rings, all substituents are attached to these rings through any available carbon or nitrogen by replacement of a hydrogen on said carbon or nitrogen. When a compound is substituted with a substituent bearing a subscript that indicates the number of said substituents can exceed 1, said substituents (when they exceed 1) are independently selected from the group of defined substituents. Further, when the subscript indicates a range, e. g. (R)i-j, then the number of substituents may be selected from the integers between i and j inclusive. When a group contains a substituent which can be hydrogen, for example R1 or R2, then, when this substituent is taken as hydrogen, it is recognized that this is equivalent to said group being unsubstituted. DESCRIPTION Accordingly, the present invention provides a compound of formula (I),
Figure imgf000011_0001
wherein, Y represents O or NR5; R1 is selected from the group consisting of hydrogen and F; R2 and R3 are independently selected from the group consisting of hydrogen and C1-C3-alkyl; ring A represents ring system selected from A1 to A12 wherein A may be optionally substituted with one or more R4;
Figure imgf000011_0002
R4 is selected from the group consisting of X, CN, (C=O)-R6, R5aC=NOR5a, OR5, N(R5)2, S(O)nR6, C1- C6-alkyl, C1-C6-haloalkyl, -C1-C6-alkyl-OR5, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-haloalkyl, C3-C12- cycloalkyl, C3-C10-halocycloalkyl, C3-C6-cycloalkyl-C1-C6-alkyl, phenyl, and C3-C6-heterocyclyl; each group of R4 may be optionally substituted by one or more groups selected from the group consisting of halogen, R5a, OR5a, SR5a, N(R5a)2, Si(R5a)3, COOR5a, CN, and CON(R5a)2; R5 is selected from the group consisting of hydrogen, C1-C4-alkyl, C3-C6-cycloalkyl and C3- C6-cycloalkyl-C1-C3-alkyl; R5a is selected from the group consisting of hydrogen, C1-C6-alkyl and C3-C6-cycloalkyl; R6 is selected from the group consisting of N(R5a)2, C1-C6-alkyl, C2-C6-alkenyl, C2-C6- alkynyl, C1-C6-haloalkyl, C2-C6-haloalkenyl, C2-C6-haloalkynyl and C3-C6-cycloalkyl; R1, R2, R3, R4, R5, R5a and R6 may optinally be substituted with one or more groups consisting of X, CN, C1-C4-alkyl, O-C1-C4-alkyl, S(O)n-C1-C4-alkyl and C3-C6-cycloalkyl; X represent halogen; n represents integers wherein n=0,1 and 2; or agriculturally acceptable salts, stereoisomer, tautomers or N-oxides thereof. In one embodiment, the present invention provides a compound of formula (I), wherein Y represent O; ring A represents ring system selected from A1 to A7 wherein A may be optionally substituted with one or more R4;
Figure imgf000012_0001
R4 is selected from the group consisting of X, CN, R5aC=NOR5a, C1-C6-alkyl, C1-C6-haloalkyl, - C1-C6-alkyl-OR5, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-haloalkyl, C3-C12-cycloalkyl, C3-C10- halocycloalkyl, C3-C6-cycloalkyl-C1-C6-alkyl, phenyl, and C3-C6-heterocyclyl; each group of R4 may be optionally substituted by one or more groups selected from the group consisting of halogen, R5a, OR5a, SR5a, N(R5a)2, Si(R5a)3, COOR5a, CN, and CON(R5a)2; preferred is selected from R4 X, CN, C1-C6-alkyl, C1-C6-haloalkyl; and/or stereoisomer or agriculturally acceptable salts or tautomers or N-oxides thereof. In one embodiment, the present invention provides a compound of formula (I), wherein ring A represents ring system selected from A8 to A12 wherein A may be optionally substituted with one or more R4;
Figure imgf000013_0001
R4 is selected from the group consisting of X, CN, R5aC=NOR5a, -C1-C6-alkyl-OR5, C1-C6- alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-haloalkyl, C3-C12-cycloalkyl, C3- C10-halocycloalkyl, C3-C6-cycloalkyl-C1-C6-alkyl, phenyl, and C3-C6-heterocyclyl; each group of R4 may be optionally substituted by one or more groups selected from the group consisting of halogen, R5a, OR5a, SR5a, N(R5a)2, Si(R5a)3, COOR5a, CN, and CON(R5a)2; and/or stereoisomer or agriculturally acceptable salts or tautomers or N-oxides thereof. In one embodiment, the present invention provides a compound of formula (I), wherein prefereably ring A is selected from A1, A2, A6 and A7 wherein A may be optionally substituted with one or more R4;
Figure imgf000013_0002
In one embodiment, the present invention provides a compound of formula (I), wherein Y represent O; ring A represents ring system selected from A1 to A12 wherein A may be optionally substituted with one or more R4; and R4 is selected from the group consisting of X, CN, C1-C6-alkyl, C1-C6-haloalkyl, R5aC=NOR5a, -C1-C6-alkyl-OR5. In one embodiment, the present invention provides a compound of formula (I), wherein preferred compounds selected from 4,4-difluorobut-3-en-1-yl 2-(5-methyl-3-(trifluoromethyl)-1H-pyrazol-1- yl)acetate; 4,4-difluorobut-3-en-1-yl 2-(3,5-bis(trifluoromethyl)-1H-pyrazol-1-yl)acetate; 4,4- difluorobut-3-en-1-yl 2-(3,5-dimethyl-1H-pyrazol-1-yl)acetate; 4,4-difluorobut-3-en-1-yl 2-(4- methyl-1H-pyrazol-1-yl)acetate; 4,4-difluorobut-3-en-1-yl 2-(3,5-bis(difluoromethyl)-1H-pyrazol-1- yl)acetate; 3,4,4-trifluorobut-3-en-1-yl 2-(5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl)acetate; 4,4- difluorobut-3-en-1-yl 2-(5-cyclopropyl-3-(trifluoromethyl)-1H-pyrazol-1-yl)acetate; 4,4-difluorobut- 3-en-1-yl 2-(4-chloro-1H-pyrazol-1-yl)acetate; 3,4,4-trifluorobut-3-en-1-yl 2-(5-cyclopropyl-3- (trifluoromethyl)-1H-pyrazol-1-yl)acetate; 3,4,4-trifluorobut-3-en-1-yl 2-(4-chloro-1H-pyrazol-1- yl)acetate; 3,4,4-trifluorobut-3-en-1-yl 2-(3,5-dimethyl-1H-pyrazol-1-yl)acetate; 3,4,4-trifluorobut-3- en-1-yl 2-(4-methyl-1H-pyrazol-1-yl)acetate; 3,4,4-trifluorobut-3-en-1-yl 2-(3,5-bis(trifluoromethyl)- 1H-pyrazol-1-yl)acetate; 4,4-difluorobut-3-en-1-yl 2-(1H-indazol-1-yl)acetate; 3,4,4-trifluorobut-3- en-1-yl 2-(1H-indazol-1-yl)acetate; 3,4,4-trifluorobut-3-en-1-yl 2-(4-chloro-1H-pyrazol-1- yl)propanoate; 4,4-difluorobut-3-en-1-yl 2-(4-chloro-1H-pyrazol-1-yl)propanoate; 3,4,4-trifluorobut- 3-en-1-yl 2-(4-chloro-1H-pyrazol-1-yl)-2-methylpropanoate; 4,4-difluorobut-3-en-1-yl 2-(4-chloro- 1H-pyrazol-1-yl)-2-methylpropanoate; 3,4,4-trifluorobut-3-en-1-yl 2-(4-chloro-3,5-dimethyl-1H- pyrazol-1-yl)acetate; 4,4-difluorobut-3-en-1-yl 2-(4-chloro-3,5-dimethyl-1H-pyrazol-1-yl)acetate; 3,4,4-trifluorobut-3-en-1-yl 2-(3,5-diphenyl-1H-pyrazol-1-yl)propanoate; 4,4-difluorobut-3-en-1-yl 2- (3,5-diphenyl-1H-pyrazol-1-yl)propanoate; 3,4,4-trifluorobut-3-en-1-yl 2-(4-methyl-1H-pyrazol-1- yl)propanoate; 4,4-difluorobut-3-en-1-yl 2-(4-methyl-1H-pyrazol-1-yl)propanoate; 3,4,4-trifluorobut- 3-en-1-yl 2-methyl-2-(4-methyl-1H-pyrazol-1-yl)propanoate; 4,4-difluorobut-3-en-1-yl 2-methyl-2- (4-methyl-1H-pyrazol-1-yl)propanoate; 3,4,4-trifluorobut-3-en-1-yl 2-(3,5-diphenyl-1H-pyrazol-1- yl)acetate; 4,4-difluorobut-3-en-1-yl 2-(3,5-diphenyl-1H-pyrazol-1-yl)acetate; 3,4,4-trifluorobut-3-en- 1-yl 2-(3-(difluoromethyl)-2H-indazol-2-yl)acetate; 3,4,4-trifluorobut-3-en-1-yl 2-(3-methyl-2H- indazol-2-yl)acetate; 4,4-difluorobut-3-en-1-yl 2-(3-methyl-1H-indazol-1-yl)acetate; 4,4-difluorobut- 3-en-1-yl 2-(3-(difluoromethyl)-2H-indazol-2-yl)acetate; 3,4,4-trifluorobut-3-en-1-yl 2-(3,5- bis(difluoromethyl)-1H-pyrazol-1-yl)acetate; 3,4,4-trifluorobut-3-en-1-yl 2-(1H-pyrazol-1-yl)acetate; 4,4-difluorobut-3-en-1-yl 2-(1H-pyrazol-1-yl)acetate; 3,4,4-trifluorobut-3-en-1-yl 2-(3- (trifluoromethyl)-1H-pyrazol-1-yl)acetate; 4,4-difluorobut-3-en-1-yl 2-(3-(trifluoromethyl)-1H- pyrazol-1-yl)acetate; 3,4,4-trifluorobut-3-en-1-yl 2-(5-methyl-3-(trifluoromethyl)-1H-pyrazol-1- yl)propanoate; 4,4-difluorobut-3-en-1-yl 2-(5-methyl-3-(trifluoromethyl)-1H-pyrazol-1- yl)propanoate; 3,4,4-trifluorobut-3-en-1-yl 2-methyl-2-(5-methyl-3-(trifluoromethyl)-1H-pyrazol-1- yl)propanoate; 4,4-difluorobut-3-en-1-yl 2-methyl-2-(5-methyl-3-(trifluoromethyl)-1H-pyrazol-1- yl)propanoate; 3,4,4-trifluorobut-3-en-1-yl 2-(2H-indazol-2-yl)acetate; 4,4-difluorobut-3-en-1-yl 2- (2H-indazol-2-yl)acetate; 3,4,4-trifluorobut-3-en-1-yl 2-(3,5-dimethyl-1H-1,2,4-triazol-1-yl)acetate; 2-(4-chloro-1H-pyrazol-1-yl)-N-(3,4,4-trifluorobut-3-en-1-yl)acetamide 3,4,4-trifluorobut-3-en-1-yl 2-(5-(trifluoromethyl)-2H-tetrazol-2-yl)acetate; 3,4,4-trifluorobut-3-en-1-yl 2-(4,5-dichloro-1H- imidazol-1-yl)acetate; 4,4-difluorobut-3-en-1-yl 2-(3,5-dimethyl-1H-1,2,4-triazol-1-yl)acetate; 4,4- difluorobut-3-en-1-yl 2-(3,5-dimethyl-1H-pyrazol-1-yl)propanoate; 4,4-difluorobut-3-en-1-yl 2-(3,5- dimethyl-1H-pyrazol-1-yl)-2-methylpropanoate; 2-(4-chloro-1H-pyrazol-1-yl)-N-(4,4-difluorobut-3- en-1-yl)acetamide 3,4,4-trifluorobut-3-en-1-yl 2-(1H-benzo[d]imidazol-1-yl)acetate; 3,4,4- trifluorobut-3-en-1-yl 2-(1H-imidazol-1-yl)acetate; 4,4-difluorobut-3-en-1-yl 2-(1H- benzo[d]imidazol-1-yl)acetate; 4,4-difluorobut-3-en-1-yl 2-(1H-imidazol-1-yl)acetate; 3,4,4- trifluorobut-3-en-1-yl 2-(4-(trifluoromethyl)-1H-pyrazol-1-yl)acetate; 3,4,4-trifluorobut-3-en-1-yl 2- (4-chloro-3,5-dimethyl-1H-pyrazol-1-yl)-2-methylpropanoate; 3,4,4-trifluorobut-3-en-1-yl 2-(4- chloro-3,5-dimethyl-1H-pyrazol-1-yl)propanoate; 4,4-difluorobut-3-en-1-yl 2-(4-chloro-3,5-dimethyl- 1H-pyrazol-1-yl)-2-methylpropanoate; 4,4-difluorobut-3-en-1-yl 2-(4-chloro-3,5-dimethyl-1H- pyrazol-1-yl)propanoate; 3,4,4-trifluorobut-3-en-1-yl 2-(3,5-dimethyl-1H-pyrazol-1-yl)propanoate; 4,4-difluorobut-3-en-1-yl 2-(2-methyl-1H-imidazol-1-yl)acetate; 4,4-difluorobut-3-en-1-yl 2-(5- methyl-2H-tetrazol-2-yl)acetate; 3,4,4-trifluorobut-3-en-1-yl 2-(5-methyl-2H-tetrazol-2-yl)acetate; 4,4-difluorobut-3-en-1-yl 2-(4-(trifluoromethyl)-1H-pyrazol-1-yl)acetate; 4,4-difluorobut-3-en-1-yl 2- (2-cyclopropyl-1H-benzo[d]imidazol-1-yl)acetate; 3,4,4-trifluorobut-3-en-1-yl 2-(1H- benzo[d][1,2,3]triazol-1-yl)acetate; 4,4-difluorobut-3-en-1-yl 2-(1H-benzo[d][1,2,3]triazol-1- yl)acetate; 3,4,4-trifluorobut-3-en-1-yl 2-(5-methyl-1H-tetrazol-1-yl)acetate; 3,4,4-trifluorobut-3-en- 1-yl 2-(3,5-bis(trifluoromethyl)-1H-pyrazol-1-yl)propanoate; 4,4-difluorobut-3-en-1-yl 2-(3,5- bis(trifluoromethyl)-1H-pyrazol-1-yl)propanoate; 3,4,4-trifluorobut-3-en-1-yl 2-(3-chloro-1H- indazol-1-yl)acetate; 3,4,4-trifluorobut-3-en-1-yl 2-(3,5-dimethyl-1H-pyrazol-1-yl)-2- methylpropanoate; 3,4,4-trifluorobut-3-en-1-yl 2-(2-methyl-1H-imidazol-1-yl)acetate; 3,4,4- trifluorobut-3-en-1-yl 2-(4,5-dichloro-2-methyl-1H-imidazol-1-yl)acetate; 3,4,4-trifluorobut-3-en-1-yl 2-(3-chloro-1H-indazol-1-yl)-2-methylpropanoate; 3,4,4-trifluorobut-3-en-1-yl 2-(1H-pyrazol-1- yl)propanoate; 3,4,4-trifluorobut-3-en-1-yl 2-methyl-2-(1H-pyrazol-1-yl)propanoate; 3,4,4- trifluorobut-3-en-1-yl 2-(3-(trifluoromethyl)-1H-pyrazol-1-yl)propanoate; 3,4,4-trifluorobut-3-en-1-yl 2-methyl-2-(3-(trifluoromethyl)-1H-pyrazol-1-yl)propanoate; 3,4,4-trifluorobut-3-en-1-yl 2-(4- phenyl-1H-pyrazol-1-yl)acetate; 3,4,4-trifluorobut-3-en-1-yl 2-(4-chloro-3-methyl-5- (trifluoromethyl)-1H-pyrazol-1-yl)acetate; 3,4,4-trifluorobut-3-en-1-yl 2-(4-chloro-5-methyl-3- (trifluoromethyl)-1H-pyrazol-1-yl)acetate; 3,4,4-trifluorobut-3-en-1-yl 2-(4-(3,5-difluorophenyl)-1H- pyrazol-1-yl)acetate; 3,4,4-trifluorobut-3-en-1-yl 2-(2H-benzo[d][1,2,3]triazol-2-yl)propanoate; 3,4,4- trifluorobut-3-en-1-yl 2-(5-methyl-2H-tetrazol-2-yl)propanoate; 3,4,4-trifluorobut-3-en-1-yl 2-(1H- benzo[d][1,2,3]triazol-1-yl)propanoate; 3,4,4-trifluorobut-3-en-1-yl 2-(2-(trifluoromethyl)-1H- benzo[d]imidazol-1-yl)acetate; 3,4,4-trifluorobut-3-en-1-yl 2-(2-methyl-1H-benzo[d]imidazol-1- yl)acetate; 3,4,4-trifluorobut-3-en-1-yl 2-(2H-benzo[d][1,2,3]triazol-2-yl)-2-methylpropanoate; 3,4,4- trifluorobut-3-en-1-yl 2-(1H-benzo[d][1,2,3]triazol-1-yl)-2-methylpropanoate; 3,4,4-trifluorobut-3-en- 1-yl 2-methyl-2-(5-methyl-2H-tetrazol-2-yl)propanoate; 3,4,4-trifluorobut-3-en-1-yl 2-(4-chloro-1H- pyrazol-1-yl)butanoate; 3,4,4-trifluorobut-3-en-1-yl 2-(4-chloro-3,5-dimethyl-1H-pyrazol-1- yl)butanoate; 3,4,4-trifluorobut-3-en-1-yl 2-(3-(trifluoromethyl)-1H-pyrazol-1-yl)butanoate; 3,4,4- trifluorobut-3-en-1-yl 2-(5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl)butanoate; 3,4,4-trifluorobut- 3-en-1-yl 2-(3,5-bis(trifluoromethyl)-1H-pyrazol-1-yl)butanoate; 3,4,4-trifluorobut-3-en-1-yl 2-(3- methyl-1H-pyrazol-1-yl)butanoate; 3,4,4-trifluorobut-3-en-1-yl 2-(3-methyl-1H-indazol-1- yl)butanoate; 3,4,4-trifluorobut-3-en-1-yl 2-(4-chloro-1H-pyrazol-1-yl)-3-methylbutanoate; 3,4,4- trifluorobut-3-en-1-yl 2-(3,5-bis(trifluoromethyl)-1H-pyrazol-1-yl)-3-methylbutanoate; 3,4,4- trifluorobut-3-en-1-yl 3-methyl-2-(3-methyl-5-(trifluoromethyl)-1H-pyrazol-1-yl)butanoate; 3,4,4- trifluorobut-3-en-1-yl 3-methyl-2-(3-methyl-5-phenyl-1H-pyrazol-1-yl)butanoate; 3,4,4-trifluorobut- 3-en-1-yl 2-(4-chloro-3,5-dimethyl-1H-pyrazol-1-yl)-3-methylbutanoate; 3,4,4-trifluorobut-3-en-1-yl 2-(3,5-diphenyl-1H-pyrazol-1-yl)-3-methylbutanoate; 3,4,4-trifluorobut-3-en-1-yl 3-methyl-2-(3- methyl-1H-pyrazol-1-yl)butanoate; 3,4,4-trifluorobut-3-en-1-yl 3-methyl-2-(3-(trifluoromethyl)-1H- pyrazol-1-yl)butanoate and 3,4,4-trifluorobut-3-en-1-yl 3-methyl-2-(4-methyl-1H-pyrazol-1- yl)butanoate. It can be advantageous to isolate or synthesize in each case an isomer that is biologically more effective, for example a specific enantiomer or diastereomer, or an isomeric mixture, for example an enantiomeric mixture or a diastereomeric mixture, if the individual components have a different biological activity. The compounds of formula (I) and, wherever appropriate, the tautomers thereof, in each case in free form or in salt form, can, if appropriate, also be obtained in the form of hydrates and/or include other solvents, for example those which may have been used for the crystallization of compounds which are present in solid form. The compounds of the present invention as defined by formula (I) and/or in table (1) can be prepared, as shown in the following schemes, in which, unless otherwise stated, the definition of each variable is as defined above for a compound of formula (I). Scheme: 1
Figure imgf000016_0001
As shown in scheme 1, a compound of formula 4 can be prepared by alkylation of a compound of formula 2 with a alkyl haloacetate compound of formula 3 in the presence of an organic or an inorganic base such as for instance potassium carbonate or cesium carbonate in the presence of a suitable solvent such as for instance acetonitrile or N,N-dimethylformamide, usually under heating conditions. Subsequently the compound of formula 4 is hydrolysed to obtain a compound of formula 5 in presence of a suitable acid or base. Suitable acids which can be used for this hydrolysis are selected from hydrochloric acid or trifluoroacetic acid, whereas a suitable base which can be used for the hydrolysis may be selected from sodium hydroxide or lithium hydroxide in the presence of a suitable solvent such as for instance tetrahydrofuran, 1,4-dioxane, methanol or water. Scheme: 2
Figure imgf000017_0001
Further, as shown in scheme 2, a compound of formula 1a can be prepared by alkylation of a compound of formula 5 with a fluorobutenyl halide compound of formula 6 in the presence of an organic or inporganic base such as N,N-diisopropylethylamine, potassium carbonate or cesium carbonate; in suitable solvents such as acetonitrile and N,N-dimethyl formamide, usually under heating conditions. Scheme: 3
Figure imgf000017_0002
As shown in scheme 3, a compound of formula 1b can be prepared by an amide coupling reaction of a compound of formula 5 with an amine of formula 6 using various coupling reagents such as N-(3- Dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (EDCI), 1- [Bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxid hexafluorophosphate (HATU), or halogenating reagent such as SOCl2, SO2Cl2, COCl2, X2, methanesulfonyl chloride, preferably in the presence of a base such as triethylamine and diisopropylethyl amine. Further the compound of formula 1c can be prepared by alkylation of a compound of formula 1b with an alkyl halide in the presence of a base such as for instance potassium carbonate, cesium carbonate and sodium hydride in the presence of a suitable solvent such as acetonitrile and N,N-dimethylformamide, usually betweent room temperature and heating conditions. Any of the compounds according to the invention can exist in one or more optical, geometric or chiral isomer forms depending on the number of asymmetric centres in the compound. The invention thus relates equally to all the optical isomers and to their racemic or scalemic mixtures (the term “scalemic” denotes a mixture of enantiomers in different proportions), and to the mixtures of all the possible stereoisomers, in all proportions. The diastereoisomers and/or the optical isomers can be separated according to the methods which are known per se by a person ordinary skilled in the art. Any of the compounds according to the invention can also exist in one or more geometric isomer forms depending on the number of double bonds in the compound. The invention thus relates equally to all geometric isomers and to all possible mixtures, in all proportions. The geometric isomers can be separated according to general methods, which are known per se by a person ordinary skilled in the art. Any of the compounds according to the invention, can also exist in one or more amorphic or isomorphic or polymorphic forms, depending on their preparation, purification storage and various other influencing factors. The invention thus relates all the possible amorphic, isomorphic and polymorphic forms, in all proportions. The amorphic, isomorphic and polymorphic forms can be prepared and/or separated and/or purified according to general methods, which are known per se by a person ordinary skilled in the art. There is a large number of suitable known standard methods, such as alkylation, halogenation, acylation, amidation, oximation, oxidation and reduction. The choice of the preparation methods which are suitable are depending on the properties (reactivity) of the substituents in the intermediates. These reactions can be conveniently performed in a solvent. They may conveniently be performed at various temperatures, usually under an inert atmosphere. The reactants can be reacted in the presence of a base. Examples of suitable bases are alkali metal or alkaline earth metal hydroxides, alkali metal or alkaline earth metal hydrides, alkali metal or alkaline earth metal amides, alkali metal or alkaline earth metal alkoxides, alkali metal or alkaline earth metal acetates, alkali metal or alkaline earth metal carbonates, alkali metal or alkaline earth metal dialkylamides or alkali metal or alkaline earth metal alkylsilylamides, alkylamines, alkylenediamines, free or N-alkylated saturated or unsaturated cycloalkylamines, basic heterocycles, ammonium hydroxides and carbocyclic amines. Examples which may be mentioned are sodium hydroxide, sodium hydride, sodium amide, sodium methoxide, sodium acetate, sodium carbonate, potassium tert-butoxide, potassium hydroxide, potassium carbonate, potassium hydride, lithium diisopropylamide, potassium bis(trimethylsilyl)amide, calcium hydride, triethylamine, N,N-diisopropylethylamine, triethylenediamine, cyclohexylamine, N- cyclohexyl-N,N-dimethylamine, N,N-diethylaniline, pyridine, 4-(N,N-dimethylamino)pyridine, quinuclidine, N-methylmorpholine, benzyltrimethylammonium hydroxide and 1,8- diazabicyclo[5.4.0]undec-7-ene (DBU). The reaction according to scheme-1 to scheme-3 is preferably carried out in a solvent selected from standard solvents which are inert under the prevailing reaction conditions. Preference is given to aliphatic, alicyclic or aromatic hydrocarbons, such as petroleum ether, hexane, toluene; halogenated hydrocarbons, such as, chlorobenzene, dichloromethane, chloroform, carbon tetrachloride or dichloroethane; ethers, such as, diethyl ether, diisopropyl ether, methyl t-butyl ether (MTBE), dioxane, tetrahydrofuran or 1,2-dimethoxyethane; nitriles, such as, acetonitrile or propionitrile, or; amides, such as, N,N-dimethylformamide (DMF), N,N-dimethylacetamide, N-methylfonnanilide, N- methylpyrrolidone (NMP) or hexamethylenephosphoric triamide; esters, such as, for example, methyl acetate or ethyl acetate; sulfoxides, such as, dimethyl sulfoxide (DMSO); sulfones, such as, sulfolane; alcohols, such as, methanol, ethanol, nor isopropanol, 1,1-, iso-, sec- or tert-butanol, ethanediol, propane-1,2-diol, ethoxyethanol, methoxyethanol, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether or mixtures of these. The reactants can be reacted with each other as such, i.e. without adding a solvent or diluent. The reaction is advantageously carried out in a temperature range from approximately -80 °C to approximately +140 °C, preferably from approximately -30 °C to approximately +100 °C, in many cases in the range between ambient temperature and approximately +80 °C. A compound of formula (I) can be converted in a manner known per se into another compound of formula (I) by replacing one or more substituents of the starting compound of formula (I) in the customary manner by (an)other substituent(s) according to the invention. Depending on the choice of the reaction conditions and starting materials which are suitable in each case, it is possible, for example, in one reaction step only to replace one substituent by another substituent according to the invention, or a plurality of substituents can be replaced by other substituents according to the invention in the same reaction step. Salts of compounds of formula (I) can be prepared in a manner known per se. Thus, for example, acid addition salts of compounds of formula (I) are obtained by treatment with a suitable acid or a suitable ion exchanger reagent and salts with bases are obtained by treatment with a suitable base or with a suitable ion exchanger reagent. A salt is chosen depending on its tolerances for compound's use, such as agricultural or physiological tolerance. Salts of compounds of formula (I) can be converted in the customary manner into the free compounds I, acid addition salts, for example, by treatment with a suitable basic compound or with a suitable ion exchanger reagent and salts with bases, for example, by treatment with a suitable acid or with a suitable ion exchanger reagent. Salts of compounds of formula (I) can be converted in a manner known per se into other salts of compounds of formula (I), acid addition salts, for example, into other acid addition salts, for example by treatment of a salt of inorganic acid such as hydrochloride with a suitable metal salt such as a sodium, barium or silver salt, of an acid, for example with silver acetate, in a suitable solvent in which an inorganic salt which forms, for example silver chloride, is insoluble and thus precipitates from the reaction mixture. In one embodiment, the present invention provides use of compound of formula (I), stereoisomers, agriculturally acceptable salts, tautomers or N-oxides thereof or composition or combination thereof for controlling or preventing agricultural crops and/or horticultural crops against phytopathogenic fungi, bacteria, insects, nematodes or mites. In preferred embodiment, the present invention provides use of compound of formula (I), stereoisomers, agriculturally acceptable salts, tautomers or N-oxides thereof or composition or combination thereof for controlling or preventing agricultural crops and/or horticultural crops against nematodes and phytopathogenic fungi. The agricultural crops are selected from cereals, corn, rice, soybean and other leguminous plants, fruits and fruit trees, 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 or ornamentals. The compounds according to the invention can be used for controlling or destroying pests such as nematodes which occur in particular in plants, especially in useful plants and ornamentals in agriculture, in horticulture and in forests, or in organs, such as tubers, seeds or roots, of such plants, and in some cases even plant organs which are formed at a later point in time remain protected against these pests. The compounds of formula (I) according to the invention are preventively and/or curatively valuable active ingredients in the field of pest control, even at low rates of application, which can be used against pesticide resistant pests such as nematodes. Additionally compounds of formula (I) have a very favorable biocidal spectrum and are well tolerated by warm-blooded species, fish and plants. Accordingly, the present invention also makes available a pesticidal composition comprising compounds of the invention, such as formula (I). It has now been found that the compounds of formula (I) according to the invention have, for practical purposes, a very advantageous spectrum of activity for protecting animals and useful plants against attack and damage by nematodesAccordingly, the present invention also makes available a nematocidal composition comprising compounds of the invention, such as formula (I The compounds of the formula (I) possess potent nematicidal activity and can be used for the control of unwanted nematodes and bacteria, in agricultural or horticultural crop protection and in the protection of such materials. The compounds of the formula (I) can be used as nematicides in crop protection, for example, for control of Tylenchida, Rhabditida, Dorylaimida, and Tryplonchida. The compounds of the formula (I) can be used for controlling or preventing against phytopathogenic nematodes of agricultural crops and or horticultural crops. The compounds of the formula (I) can be used in crop protection, wherein the agricultural crops are cereals, corn, rice, soybean and other leguminous plants, fruits and fruit trees, 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 other vegetables, and ornamentals. The compounds of formula (I) are especially useful for the control of nematodes. Thus, in a further aspect, the invention also relates to a method of controlling damage to plant and parts thereof by plant parasitic nematodes (Endoparasitic, Semiendoparasitic and Ectoparasitic nematodes), especially plant parasitic nematodes such as root knot nematodes, Meloidogyne hapla, Meloidogyne incognita, Meloidogyne javanica, Meloidogyne arenaria 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, Eelonolaimus longicaudatus and other Belonolaimus species; Pine nematodes, Bursaphelenchus xylophilus and other Bursaphelenchus species; Ring nematodes, Criconema species, Criconemella species, Criconemoides species, Mesocriconema species; Stem and bulb nematodes, Ditylenchus destructor, Ditylenchus dipsaci and other Ditylenchus species; Awl nematodes, Dolichodorus species; Spiral nematodes, Heliocotylenchus multicinctus and other Helicotylenchus species; Sheath and sheathoid nematodes, Hemicycliophora species and Hemicriconemoides species; Hirshmanniella species; Lance nematodes, Hoploaimus species; false rootknot nematodes, Nacobbus species; Needle nematodes, Longidorus elongatus and other Longidorus species; Pin nematodes, Pratylenchus species; Lesion nematodes, Pratylenchus neglectus, Pratylenchus penetrans, Pratylenchus curvitatus, Pratylenchus goodeyi and other Pratylenchus species; Burrowing nematodes, Radopholus similis and other Radopholus species; Reniform nematodes, Rotylenchus robustus, Rotylenchus reniformis and other Rotylenchus species; Scutellonema species; Stubby root nematodes, Trichodorus primitivus and other Trichodorus species, Paratrichodorus species; Stunt nematodes, Tylenchorhynchus claytoni, Tylenchorhynchus dubius and other Tylenchorhynchus species; Citrus nematodes, Tylenchulus species; Dagger nematodes, Xiphinema species; and other plant parasitic nematode species, such as Subanguina spp., Hypsoperine spp., Macroposthonia spp., Melinius spp., Punctodera spp., and Quinisulcius spp.. Particularly, the nematode species Meloidogyne spp., Heterodera spp., Rotylenchus spp., Pratylenchus spp. and Radopholus spp. can be controlled by compounds of the invention. In one embodiment, the present invention provides a composition for controlling or preventing phytopathogenic microorganisms comprising a compound of general formula (I), stereoisomer, agriculturally acceptable salts, tautomers or N-oxides thereof and one or more inert carriers. In another embodiment, the composition may additionally comprises one or more active compatible compounds selected from fungicides, insecticides, nematicides, acaricides, biopesticides, herbicides, plant growth regulators, antibiotics, nutrients or fertilizers. The concentration of the compound of general formula (I) ranges from 1 to 90% 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 further relates to a composition for controlling unwanted microorganisms comprising at least one of the compounds of the formula (I) and one or more inert carrier. The inert carrier further comprises agriculturally suitable auxiliaries, solvents, diluents, surfactants and/or extenders and the like. The present invention further relates to a composition for controlling unwanted microorganisms, comprising at least one of the compounds of the formula (I) and/or one or more active compatible compound selected from fungicides, bactericides, acaricides, insecticides, nematicides, herbicides, biopesticides, plant growth regulators, antibiotics, fertilizers and/or mixtures thereof. Generally, a compound of the present invention is used in the form of a composition (e.g.formulation) containing a carrier. A compound of the invention and compositions thereof can be used in various forms such as aerosol dispenser, capsule suspension, cold fogging concentrate, dustable powder, emulsifiable concentrate, emulsion oil in water, emulsion water in oil, encapsulated granule, fine granule, flowable concentrate for seed treatment, gas (under pressure), gas generating product, granule, hot fogging concentrate, macrogranule, microgranule, oil dispersible powder, oil miscible flowable concentrate, oil miscible liquid, paste, plant rodlet, powder for dry seed treatment, seed coated with a pesticide, soluble concentrate, soluble powder, solution for seed treatment, suspension concentrate (flowable concentrate), ultra-low volume (ulv) liquid, ultra-low volume (ulv) suspension, water dispersible granules or tablets, water dispersible powder for slurry treatment, water soluble granules or tablets, water soluble powder for seed treatment and wettable powder. A formulation typically comprises a liquid or solid carrier and optionally one or more customary formulation auxiliaries, which may be solid or liquid auxiliaries, for example unepoxidized or epoxidized vegetable oils (for example epoxidized coconut oil, rapeseed oil or soya oil), antifoams, for example silicone oil, preservatives, clays, inorganic compounds, viscosity regulators, surfactant, binders and/or tackifiers. The composition may also further comprise a fertilizer, a micronutrient donor or other preparations which influence the growth of plants as well as comprising a combination containing the compound of the invention with one or more other biologically active agents, such as bactericides, fungicides, nematicides, plant activators, acaricides, and insecticides. Accordingly, the present invention also makes available a composition comprising a compound of the invention and an agronomical carrier and optionally one or more customary formulation auxiliaries. The compositions are prepared in a manner known per se, in the absence of auxiliaries for example by grinding, screening and/or compressing a solid compound of the present invention and in the presence of at least one auxiliary for example by intimately mixing and/or grinding the compound of the present invention with the auxiliary (auxiliaries). In the case of solid compounds of the invention, the grinding/milling of the compounds is to ensure specific particle size. These processes for the preparation of the compositions and the use of the compounds of the invention for the preparation of these compositions are also a subject of the invention. Examples of compositions for use in agriculture are emulsifiable concentrates, suspension concentrates, microemulsions, oil dispersibles, directly sprayable or dilutable solutions, spreadable pastes, dilute emulsions, soluble powders, dispersible powders, wettable powders, dusts, granules or encapsulations in polymeric substances, which comprise - at least - a compound according to the invention and the type of composition is to be selected to suit the intended aims and the prevailing circumstances. Examples of suitable liquid carriers are unhydrogenated or partially hydrogenated aromatic hydrocarbons, preferably the fractions C8 to C12 of alkylbenzenes, such as xylene mixtures, alkylated naphthalenes or tetrahydronaphthalene, aliphatic or cycloaliphatic hydrocarbons, such as paraffins or cyclohexane, alcohols such as ethanol, propanol or butanol, glycols and their ethers and esters such as propylene glycol, dipropylene glycol ether, ethylene glycol or ethylene glycol monomethyl ether or ethylene glycol monoethyl ether, ketones, such as cyclohexanone, isophorone or diacetone alcohol, strongly polar solvents, such as N-methylpyrrolid-2-one, dimethyl sulfoxide or N,N- dimethylformamide, water, unepoxidized or epoxidized vegetable oils, such as unexpodized or epoxidized rapeseed, castor, coconut or soya oil, and silicone oils. Examples of solid carriers which are used for example for dusts and dispersible powders are, as a rule, ground natural minerals such as calcite, talc, kaolin, montmorillonite or attapulgite. To improve the physical properties, it is also possible to add highly disperse silicas or highly disperse absorbtive polymers. Suitable particulate adsorptive carriers for granules are porous types, such as pumice, brick grit, sepiolite or bentonite, and suitable non-sorptive carrier materials are calcite or sand. In addition, a large number of granulated materials of inorganic or organic nature can be used, in particular dolomite or comminuted plant residues. Suitable surface-active compounds are, depending on the type of the active ingredient to be formulated, non-ionic, cationic and/or anionic surfactants or surfactant mixtures which have good emulsifying, dispersing and wetting properties. The surfactants mentioned below are only to be considered as examples; a large number of further surfactants which are conventionally used in the art of formulation and suitable according to the invention are described in the relevant literature. Suitable non-ionic surfactants are, especially, polyglycol ether derivatives of aliphatic or (cyclo)aliphatic alcohols, of saturated or unsaturated fatty acids or of alkyl phenols which may contain approximately 3 to approximately 30 glycol ether groups and approximately 8 to approximately 20 carbon atoms in the (cyclo)aliphatic hydrocarbon radical or approximately 6 to approximately 18 carbon atoms in the alkyl moiety of the alkyl phenols. Also suitable are water-soluble polyethylene oxide adducts with polypropylene glycol, ethylenediaminopolypropylene glycol or alkyl polypropylene glycol having 1 to approximately 10 carbon atoms in the alkyl chain and approximately 20 to approximately 250 ethylene glycol ether groups and approximately 10 to approximately 100 propylene glycol ether groups. Normally, the abovementioned compounds contain 1 to approximately 5 ethylene glycol units per propylene glycol unit. Examples which may be mentioned are nonylphenoxypolyethoxyethanol, castor oil polyglycol ether, polypropylene glycol/polyethylene oxide adducts, tributylphenoxypolyethoxyethanol, polyethylene glycol or octylphenoxypolyethoxyethanol. Also suitable are fatty acid esters of polyoxyethylene sorbitan, such as polyoxyethylene sorbitan trioleate. The cationic surfactants are, especially, quarternary ammonium salts which generally have at least one alkyl radical of approximately 8 to approximately 22 Carbon atoms as substituents and as further substituents (unhalogenated or halogenated) lower alkyl or hydroxyalkyl or benzyl radicals. The salts are preferably in the form of halides, methylsulfates or ethylsulfates. Examples are stearyltrimethylammonium chloride and benzylbis(2-chloroethyl)ethylammonium bromide. Examples of suitable anionic surfactants are water-soluble soaps or water-soluble synthetic surface- active compounds. Examples of suitable soaps are the alkali, alkaline earth or (unsubstituted or substituted) ammonium salts of fatty acids having approximately 10 to approximately 22 Carbon atoms, such as the sodium or potassium salts of oleic or stearic acid, or of natural fatty acid mixtures which are obtainable for example from coconut or tall oil; mention must also be made of the fatty acid methyl taurates. However, synthetic surfactants are used more frequently, in particular fatty sulfonates, fatty sulfates, sulfonated benzimidazole derivatives or alkylaryl sulfonates. As a rule, the fatty sulfonates and fatty sulfates are present as alkali, alkaline earth or (substituted or unsubstituted) ammonium salts and they generally have an alkyl radical of approximately 8 to approximately 22 Carbon atoms, alkyl also to be understood as including the alkyl moiety of acyl radicals; examples which may be mentioned are the sodium or calcium salts of lignosulfonic acid, of the dodecylsulphuric ester or of a fatty alcohol sulfate mixture prepared from natural fatty acids. This group also includes the salts of the sulphuric esters and sulfonic acids of fatty alcohol/ethylene oxide adducts. The sulfonated benzimidazole derivatives preferably contain 2 sulphonyl groups and a fatty acid radical of approximately 8 to approximately 22 Carbon atoms. Examples of alkylarylsulfonates are the sodium, calcium or triethanolammonium salts of decylbenzenesulfonic acid, of dibutylnaphthalenesulfonic acid or of a naphthalenesulfonic acid/formaldehyde condensate. Also possible are, furthermore, suitable phosphates, such as salts of the phosphoric ester of a p- nonylphenol/(4-14)ethylene oxide adduct, or phospholipids. As a rule, the compositions comprise 0.1 to 99%, especially 0.1 to 95%, of compound according to the present invention and 1 to 99.9%, especially 5 to 99.9%, of at least one solid or liquid carrier, it being possible as a rule for 0 to 25%, especially 0.1 to 20%, of the composition to be surfactants (% in each case meaning percent by weight). Whereas concentrated compositions tend to be preferred for commercial goods, the end consumer as a rule uses dilute compositions which have substantially lower concentrations of active ingredient. Examples of foliar formulation types for pre-mix compositions are:
Figure imgf000024_0001
Whereas, examples of seed treatment formulation types for pre-mix compositions are:
Figure imgf000024_0002
Examples of formulation types suitable for tank-mix compositions are solutions, diluted emulsions, suspensions, or a mixture thereof, and dusts. As with the nature of the formulations, the methods of application, such as foliar, drench, spraying, atomizing, dusting, scattering, coating or pouring, are chosen in accordance with the intended objectives and the prevailing circumstances. The tank-mix compositions are generally prepared by diluting with a solvent (for example, water) the one or more pre-mix compositions containing different pesticides, and optionally further auxiliaries. Suitable carriers and adjuvants can be solid or liquid and are the substances ordinarily employed in formulation technology, e.g. natural or regenerated mineral substances, solvents, dispersants, wetting agents, tackifiers, thickeners, binders or fertilizers. Generally, a tank-mix formulation for foliar or soil application comprises 0.1 to 20%, especially 0.1 to 15%, of the desired ingredients, and 99.9 to 80%, especially 99.9 to 85%, of a solid or liquid auxiliaries (including, for example, a solvent such as water), where the auxiliaries can be a surfactant in an amount of 0 to 20%, especially 0.1 to 15%, based on the tank-mix formulation. Typically, a pre- mix formulation for foliar application comprises 0.1 to 99.9%, especially 1 to 95%, of the desired ingredients, and 99.9 to 0.1%, especially 99 to 5%, of a solid or liquid adjuvant (including, for example, a solvent such as water), where the auxiliaries can be a surfactant in an amount of 0 to 50%, especially 0.5 to 40%, based on the pre-mix formulation. Normally, a tank-mix formulation for seed treatment application comprises 0.25 to 80%, especially 1 to 75%, of the desired ingredients, and 99.75 to 20%, especially 99 to 25%, of a solid or liquid auxiliaries (including, for example, a solvent such as water), where the auxiliaries can be a surfactant in an amount of 0 to 40%, especially 0.5 to 30%, based on the tank-mix formulation. Typically, a pre-mix formulation for seed treatment application comprises 0.5 to 99.9%, especially 1 to 95%, of the desired ingredients, and 99.5 to 0.1%, especially 99 to 5%, of a solid or liquid adjuvant (including, for example, a solvent such as water), where the auxiliaries can be a surfactant in an amount of 0 to 50%, especially 0.5 to 40%, based on the pre-mix formulation whereas commercial products will preferably be formulated as concentrates (e.g., pre-mix composition (formulation)), the end user will normally employ diluted formulations (e.g., tank mix composition). Preferred seed treatment pre-mix formulations are aqueous suspension concentrates. The formulation can be applied to the seeds using conventional treating techniques and machines, such as fluidized bed techniques, the roller mill method, roto static seed treaters, and drum coaters. Other methods, such as spouted beds may also be useful. The seeds may be pre sized before coating. After coating, the seeds are typically dried and then transferred to a sizing machine for sizing. Such procedures are known in the art. The compounds of the present invention are particularly suited for use in soil and seed treatment applications. In general, the pre-mix compositions of the invention contain 0.5 to 99.9% especially 1 to 95%, advantageously 1 to 50%, by mass of the desired ingredients, and 99.5 to 0.1%, especially 99 to 5%, by mass of a solid or liquid adjuvant (including, for example, a solvent such as water), where the auxiliaries (or adjuvant) can be a surfactant in an amount of 0 to 50%, especially 0.5 to 40%, by mass based on the mass of the pre-mix formulation. A compound of the formula (I) in a preferred embodiment, independent of any other embodiments, is in the form of a plant propagation material treating (or protecting) composition, wherein said plant propagation material protecting composition may comprises additionally a coloring agent. The plant propagation material protecting composition or mixture may also comprise at least one polymer from water-soluble and water-dispersible film-forming polymers that improve the adherence of the active ingredients to the treated plant propagation material, which polymer generally has an average molecular weight of at least 10,000 to about 100,000. In an embodiment, the present invention provides a method of controlling or preventing infestation of useful plants by phytopathogenic microorganisms in agricultural crops and/or horticultural crops, wherein the compound of general formula (I) and/or stereoisomers or agriculturally acceptable salts or tautomers or N-oxides thereof or composition or combination thereof, is applied to the plants, to parts thereof or a locus thereof. In another embodiment, the present invention provides a method of controlling or preventing infestation of useful plants by phytopathogenic nematodes in agricultural crops and/or horticultural crops, wherein the compound of general formula (I) and/or stereoisomers or agriculturally acceptable salts or tautomers or N-oxides thereof or composition or combination thereof is applied to a seeds of plants. In yet another embodiment, the present invention provides a method of controlling or preventing phytopathogenic nematodes in agricultural crops and/or horticultural crops using the compound of general formula (I) and/or stereoisomers or agriculturally acceptable salts or tautomers or N-oxides thereof or composition or combination thereof comprising a step of applying an effective dosage of the compound or the composition or the combination, in amounts ranging from 1 g to 5 kg per hectare of agricultural and/or horticultural crops. Examples of application methods for the compounds of the invention and compositions thereof, that is the methods of controlling pests in the agriculture, are spraying, atomizing, dusting, brushing on, dressing, scattering or pouring which are to be selected to suit the intended aims of the prevailing circumstances. One method of application in agriculture 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 or fungi in question. Alternatively, the active ingredient can reach the plants via the root system (systemic action), by applying the compound to the locus of the plants, for example by application of a liquid composition of the compound into the soil (by drenching), or by applying a solid form of the compound in the form of granules to the soil (soil application). In the case of paddy rice plants, such granules can be metered into the flooded paddy-field. The application of the compounds of the present invention to the soil is a preferred application method. Typical rates of application per hectare is generally 1 to 2000 g of active ingredient per hectare, in particular 10 to 1000 g/ha, preferably 10 to 600 g/ha, such as 50 to 300 g/ha. In one embodiment, the present invention provides a seed comprising compound of formula (I) and/or stereoisomers, agriculturally acceptable salts, tautomers, N-oxides thereof or composition or combination thereof, wherein the amount of the compound of the formula (I) or an N-oxide or an agriculturally acceptable salt thereof is ranging from 0.1 g to 10 kg per 100 kg of seed. The compounds of the invention and compositions thereof are also suitable for the protection of plant propagation material, for example seeds, such as fruit, tubers or kernels, or nursery plants, against pests of the abovementioned type. The propagation material can be treated with the compound prior to planting, for example seed can be treated prior to sowing. Alternatively, the compound can be applied to seed kernels (coating), either by soaking the kernels in a liquid composition or by applying a layer of a solid composition. It is also possible to apply the compositions when the propagation material is planted to the site of application, for example into the seed furrow during drilling. These treatment methods for plant propagation material and the plant propagation material thus treated are further subjects of the invention. Typical treatment rates would depend on the plant and nematodes to be controlled and are generally between 1 to 200 grams per 100 kg of seeds, preferably between 5 to 150 grams per 100 kg of seeds, such as between 10 to 100 grams per 100 kg of seeds. The application of the compounds of the present invention to seeds is a preferred application method. The term seed embraces seeds and plant propagules of all kinds including but not limited to true seeds, seed pieces, suckers, corns, bulbs, fruit, tubers, grains, rhizomes, cuttings, cut shoots and the like and means in a preferred embodiment true seeds. The present invention also comprises seeds coated or treated with or containing a compound of formula I. The term “coated or treated with and/or containing” generally signifies that the active ingredient is for the most part on the surface of the seed at the time of application, although a greater or lesser part of the ingredient may penetrate into the seed material, depending on the method of application. When the said seed product is (re)planted, it may absorb the active ingredient. In an embodiment, the present invention makes available a plant propagation material adhered thereto with a compound of formula (I). Further, it is hereby made available, a composition comprising a plant propagation material treated with a compound of formula (I). Seed treatment comprises all suitable seed treatment techniques known in the art, such as seed dressing, seed coating, seed dusting, seed soaking and seed pelleting. The seed treatment application of the compound formula I, which is a preferred application method, can be carried out by any known methods, such as spraying or by dusting the seeds before sowing or during the sowing/planting of the seeds. Suitable target plants are, in particular, cereals, such as wheat, barley, rye, oats, rice, maize or sorghum; beet, such as sugar or fodder beet; fruit, for example banana, pomaceous fruit, stone fruit or soft fruit, such as apples, pears, plums, peaches, almonds, cherries or berries, for example strawberries, raspberries or blackberries; leguminous plants, such as beans, lentils, peas or soya; oil plants, such as oilseed rape, mustard, poppies, olives, sunflowers, coconut, castor, cocoa or ground nuts; cucurbits, such as pumpkins, cucumbers or melons; fibre plants, such as cotton, flax, hemp or jute; citrus fruit, such as oranges, lemons, grapefruit or tangerines; vegetables, such as spinach, lettuce, asparagus, cabbages, carrots, onions, tomatoes, potatoes or bell peppers; Lauraceae, such as avocado, Cinnamonium or camphor; and also tobacco, nuts, coffee, eggplants, sugarcane, tea, pepper, grapevines, hops, the plantain family, latex plants and ornamentals (such as flowers, and lawn grass or turf). In an embodiment, the plant is selected from cereals, corn, soybean, rice, sugarcane, vegetables and oil plants. The term “plant” is to be understood as including also plants which have been so transformed by the use of recombinant DNA techniques that they are capable of synthesizing one or more selectively acting toxins, such as are known, for example, from toxin-producing bacteria, especially those of the genus Bacillus and also plants which have been selected or hybridized to preserve and / or attain a desired trait, such as insect, fungi and /or nematode resistance. Toxins that can be expressed by such transgenic plants include, for example, insecticidal proteins from Bacillus cereus or Bacillus popilliae; or insecticidal proteins from Bacillus thuringiensis, such as 8-endotoxins, e.g. Cry1Ab, Cry1Ac, Cry1F, Cry1Fa2, Cry2Ab, Cry3A, Cry3Bb1 or Cry9C, or vegetative insecticidal proteins (Vip), e.g. Vip1, Vip2, Vip3 or Vip3A; or insecticidal proteins of bacteria colonising nematodes, for example Photorhabdus spp. or Xenorhabdus spp., such as Photorhabdus luminescens, Xenorhabdus nematophilus; toxins produced by animals, such as scorpion toxins, arachnid toxins, wasp toxins and other insect-specific neurotoxins; toxins produced by fungi, such as Streptomycetes toxins, plant lectins, such as pea lectins, barley lectins or snowdrop lectins; agglutinins; proteinase inhibitors, such as trypsin inhibitors, serine protease inhibitors, patatin, cystatin, papain inhibitors; ribosome- inactivating proteins (RIP), such as ricin, maize-RIP, abrin, luffin, saporin or bryodin; steroid metabolism enzymes, such as 3-hydroxysteroidoxidase, ecdysteroid-UDP-glycosyl- transferase, cholesterol oxidases, ecdysone inhibitors, HMG-COA-reductase, ion channel blockers, such as blockers of sodium or calcium channels, juvenile hormone esterase, diuretic hormone receptors, stilbene synthase, bibenzyl synthase, chitinases and glucanases. In the context of the present invention there are to be understood by 8-endotoxins, for example Cry1Ab, Cry1Ac, Cry1F, Cry1Fa2, Cry2Ab, Cry3A, Cry3Bb1 or Cry9C, or vegetative insecticidal proteins (Vip), for example Vip1, Vip2, Vip3 or Vip3A, expressly also hybrid toxins, truncated toxins and modified toxins. Hybrid toxins are produced recombinantly by a new combination of different domains of those proteins (see, for example, WO 02/15701). Truncated toxins, for example a truncated Cry1Ab, are known. In the case of modified toxins, one or more amino acids of the naturally occurring toxin are replaced. In such amino acid replacements, preferably non-naturally present protease recognition sequences are inserted into the toxin, such as, for example, in the case of Cry3A055, a cathepsin-G- recognition sequence is inserted into a Cry3A toxin (see WO 03/018810). Examples of such toxins or transgenic plants capable of synthesising such toxins are disclosed, for example, in EP-A-0 374 753, WO 93/07278, WO 95/34656, EP-A-0427529, EP-A-451878 and WO 03/052073. The processes for the preparation of such transgenic plants are generally known to the person skilled in the art and are described, for example, in the publications mentioned above. Cryl-type deoxyribonucleic acids and their preparation are known, for example, from WO 95/34656, EP-A-0367474, EP-A-0401979 and WO 90/13651. The toxin contained in the transgenic plants imparts to the plants tolerance to harmful insects. Such insects can occur in any taxonomic group of insects, but are especially commonly found in the beetles (Coleoptera), two-winged insects (Diptera) and butterflies (Lepidoptera).Transgenic plants containing one or more genes that code for an insecticidal resistance and express one or more toxins are known and some of them are commercially available. Examples of such plants are: YieldGard® (maize variety that expresses a Cry1Ab toxin); YieldGard Rootworm® (maize variety that expresses a Cry3Bb1 toxin); YieldGard Plus® (maize variety that expresses a Cry1Ab and a Cry3Bb1 toxin); Starlink® (maize variety that expresses a Cry9C toxin); HerculexI® (maize variety that expresses a Cry1Fa2 toxin and the enzyme phosphinothricine N-acetyltransferase(PAT) to achieve tolerance to the herbicide glufosinate ammonium); NuCOTN 33B® (cotton variety that expresses a Cry1Ac toxin); Bollgard I® (cotton variety that expresses a Cry1Ac toxin); Bollgard II® (cotton variety that expresses a Cry1Ac and a Cry2Ab toxin); VipCot® (cotton variety that expresses a Vip3A and a Cry1Ab toxin); Newleaf® (potato variety that expresses a Cry3A toxin); NatureGard®, 25Agrisure® GT Advantage (GA21 glyphosate-tolerant trait), Agrisure® CB Advantage (Bt11 corn borer (CB) trait) and Protecta®. Further examples of such transgenic plants are: i) Bt11 Maize from Syngenta Seeds SAS, Chemin de l'Hobit 27, F-31790 St. Sauveur, France, registration number C/FR/96/05/10. Genetically modified Zea mays which has been rendered resistant to attack by the European corn borer (Ostrinia nubi/alis and Sesamia nonagrioides) by transgenic expression of a truncated Cry1Ab toxin. Bt11 maize also transgenically expresses the enzyme PAT to achieve tolerance to the herbicide glufosinate ammonium; ii)Bt176 Maize from Syngenta Seeds SAS, Chemin de l'Hobit 27, F-31790 St. Sauveur, France, registration number C/FR/96/05/10. Genetically modified Zea mays which has been rendered resistant to attack by the European corn borer (Ostrinia nubi/alis and Sesamia nonagrioides) by transgenic expression of a Cry1Ab toxin. Bt176 maize also transgenically expresses the enzyme PAT to achieve tolerance to the herbicide glufosinate ammonium; iii) MIR604 Maize from Syngenta Seeds SAS, Chemin de l'Hobit 27, F-31790 St. Sauveur, France, registration number C/FR/96/05/10. Maize which has been rendered insect-resistant by transgenic expression of a modified Cry3A toxin. This toxin is Cry3A055 modified by insertion of a cathepsin-G-protease recognition sequence. The preparation of such transgenic maize plants is described in WO 03/018810; iv)MON 863 Maize from Monsanto Europe S.A. 270-272 Avenue de Tervuren, B-1150 Brussels, Belgium, registration number C/DE/02/9. MON 863 expresses a Cry3Bb1 toxin and has resistance to certain Coleoptera insects; v) IPC 531 Cotton from Monsanto Europe S.A. 270-272 Avenue de Tervuren, B-1150 Brussels, Belgium, registration number C/ES/96/02; vi) 1507 Maize from Pioneer Overseas Corporation, Avenue Tedesco, 7 B-1160 Brussels, Belgium, registration number C/NL/00/10. Genetically modified maize for the expression of the protein Cry1F for achieving resistance to certain Lepidoptera insects and of the PAT protein for achieving tolerance to the herbicide glufosinate ammonium; vii) NK603 x MON 810 Maize from Monsanto Europe S.A. 270- 272 Avenue de Tervuren, B-1150 Brussels, Belgium, registration number C/GB/02/M3/03.Consists of conventionally breed hybrid maize varieties by crossing the genetically modified varieties NK603 and MON 810. NK603 x MON 810 Maize transgenically expresses the protein CP4 EPSPS, obtained from Agrobacterium sp. strain CP4, which imparts tolerance to the herbicide Roundup® (contains glyphosate), and also a Cry1Ab toxin obtained from Bacillus thuringiensis subsp. kurstaki which brings about tolerance to certain Lepidoptera, include the European corn borer. In one embodiment, the present invention provides a combination comprising the compound of general formula (I), stereoisomer, agriculturally acceptable salts, tautomers or N-oxides thereof and one or more active compatible compound selected from fungicides, insecticides, nematicides, acaricides, biopesticides, herbicides, plant growth regulators, antibiotics, nutrients or fertilizers. Compounds of this invention are effective for controlling nematodes and/or fungal pathogens of agronomic plants, both growing and harvested, when employed alone, they may also be used in combination with other biological active agents used in agriculture, such as one or more nematocides, insecticides, acaricides, fungicides, bactericides, plant activator, molluscicide, and pheromones (whether chemical or biological). Mixing the compounds of the invention or the compositions thereof in the use form as pesticides with other pesticides frequently results in a broader pesticidal spectrum of action. For example, the formula (I) compounds of this invention may be used effectively in conjunction or combination with pyrethroids, neonicotinoids, macrolides, diamides, phosphates, carbamates, cyclodienes, formamidines, phenol tin compounds, chlorinated hydrocarbons, benzoylphenyl ureas, pyrroles and the like. The activity of the compositions according to the invention can be broadened considerably, and adapted to prevailing circumstances, by adding, for example, one or more insecticidally, acaricidally, nematicidally and/or fungicidally active agents. The combinations compounds of formula (I) with other insecticidally, acaricidally, nematicidally and/or fungicidally active agents may also have further surprising advantages. For example, better tolerance by plants, reduced phytotoxicity, pests or fungi can be controlled in their different development stages or better behavior during their production, for example during grinding or mixing, during their storage or during their use. The known and reported active compounds such as fungicides, insecticides, nematicides, acaricides, biopesticides, herbicides, safeners, plant growth regulators, antibiotics, fertilizers and nutrients can be combined with at least one compound of formula I of the present invention. For example, fungicides, insecticides, nematicides, acaricides, biopesticides, herbicides, safeners, plant growth regulators, antibiotics, fertilizers and nutrients disclosed and reported in WO2017076739 (A to O) can be combined with compound of Formula I of the present invention. The present invention also relates to such combinations comprising the compound of the present invention and active compatible compounds reported in WO2017076739. The compounds of formula (I) of the present invention can also be combined with other insecticidal active compounds of unknown or uncertain mode of action: afidopyropen, afoxolaner, azadirachtin, amidoflumet, benzoximate, bifenazate, broflanilide, bromopropylate, chinomethionat, cryolite, dicloromezotiaz, dicofol, flufenerim, flometoquin, fluensulfone, fluhexafon, fluopyram, flupyradifurone, fluralaner, metoxadiazone, piperonyl butoxide, pyflubumide, pyridalyl, pyrifluquinazon, sulfoxaflor, tioxazafen, triflumezopyrim, 11-(4-chloro-2,6-dimethylphenyl)-12- hydroxy-1,4-dioxa-9-azadispiro[4.2.4.2]-tetradec-11-en-10-one, 3-(4' -fluoro-2,4-dimethylbiphenyl-3- yl)-4-hydroxy-8-oxa-1-azaspiro[4.5]dec-3-en-2-one, 1-[2-fluoro-4-methyl-5-[(2,2,2- trifluoroethyl)sulfinyl]phenyl]-3-(trifluoromethyl)-1 H-1,2,4-triazole-5-amine, Bacillus firmus;(E/Z)- N-[1-[ (6-ch loro-3-pyridyl) methyl]-2-pyridylidene ]-2,2,2-trifluoro-acetamide; (E/Z)-N-[1-[(6- chloro-5-fluoro-3-pyridyl)methyl]-2-pyridylidene]-2,2,2-trifluoro-acetamide; (E/Z)-2,2,2-trifluoro-N- [1-[(6-fluoro-3-pyridyl)methyl]-2-pyridylidene]acetamide; (E/Z)-N-[1-[(6-bromo-3-pyridyl)methyl]- 2-pyridylidene]-2,2,2-trifluoroacetamide; (E/Z)-N-[1-[1-(6-chloro-3-pyridyl)ethyl]-2-pyridylidene]- 2,2,2-trifluoroacetamide; (E/Z)-N-[1-[(6-chloro-3-pyridyl)methyl]-2-pyridylidene]-2,2-difluoro- acetamide; (E/Z)-2-chloro-N-[ 1-[ ( 6-chloro-3-pyridyl) methyl]-2-pyridylidene]-2,2-difluoro- acetamide; (E/Z)-N-[1-[(2-chloropyrimidin-5-yl)methyl]-2-pyridylidene]-2,2,2-trifluoro-acetamide; (E/Z)-N-[1-[(6-chloro-3-pyridyl)methyl]-2-pyridylidene]-2,2,3,3,3-pentafluoro-propanamide); N-[1-[ (6-chloro-3-pyridyl)methyl]-2-pyridylidene]-2,2,2-trifluoro-thioacetamide; N-[1-[(6-chloro-3- pyridyl)methyl]-2-pyridylidene]-2,2,2-trifluoro-N'-isopropyl-acetamidine; fluazaindolizine; 4-[5-(3,5- dichlorophenyl)-5-(trifluoromethyl)-4H-isoxazol-3-yl]-2-methyl-N-(1-oxothietan-3-yl)benzamide; fluxametamide; 5-[3-[2,6-dichloro-4-(3,3-dichloroallyloxy)phenoxy]propoxy]-1H-pyrazole; 3- (benzoylmethylamino)-N-[2-bromo-4-[1,2,2,3,3,3-hexafluoro-1-(trifluoromethyl)propyl]-6- (trifluoromethyl)phenyl]-2-fluoro-benzamide; 3-(benzoylmethylamino)-2-fluoro-N-[2-iodo-4- [1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]-6-(trifluoromethyl)phenyl]-benzamide; N-[3-[[[2-iodo- 4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]-6-(trifluoromethyl)phenyl]amino]carbonyl]phenyl]-N- methyl-benzamide; N-[3-[[[2-bromo-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]-6- (trifluoromethyl)phenyl]amino]carbonyl]-2-fluorophenyl]-4-fluoro-N-methylbenzamide; 4-fluoro-N- [2-fluoro-3-[[[2-iodo-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]-6- (trifluoromethyl)phenyl]amino]carbonyl]phenyl]-N-methyl-benzamide; 3-fluoroN-[2-fluoro-3-[[[2- iodo-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]- 6(trifluoromethyl)phenyl]amino]carbonyl]phenyl]-N-methyl-benzamide; 2-chloro-N-[3-[[[2-iodo-4- [1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]-6-(trifluoromethyl)phenyl]amino]carbonyl]phenyl]-3- pyridinecarboxamide; 4-cyano-N-[2-cyano-5-[[2,6-dibromo-4-[1,2,2,3,3,3-hexafluoro-1- (trifluoromethyl) propyl]phenyl]carbamoyl]phenyl]-2-methyl-benzamide;4-cyano-3-[(4-cyano-2- methyl-benzoyl)amino]-N-[2,6-dichloro-4-[1,2,2,3,3,3-hexafluoro-1-(trifluoromethyl) propyl]phenyl]- 2-fluoro-benzamide; N-[5-[[2-chloro-6-cyano-4-[1,2,2,3,3,3-hexafluoro-1- (trifluoromethyl)propyl]phenyl]carbamoyl]-2-cyano-phenyl]-4-cyano-2-methyl-benzamide; N-[5-[[2- bromo-6-chloro-4-[2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl]phenyl]carbamoyl]-2-cyano- phenyl]-4-cyano-2-methyl-benzamide;N-[5-[[2-bromo-6-chloro-4-[1,2,2,3,3,3-hexafluoro-1- (trifluoromethyl) propyl]phenyl]carbamoyl]-2-cyano-phenyl]-4-cyano-2-methyl-benzamide; 4-cyano- N-[2-cyano-5-[[2,6-dichloro-4-[1,2,2,3,3,3-hexafluoro-1-(trifluoromethyl)propyl]phenyl]carbamoyl] phenyl]-2-methyl-benzamide; 4-cyano-N-[2-cyano-5-[[2,6-dichloro-4-[1,2,2,2-tetrafluoro-1- (trifluoromethyl)ethyl]phenyl]carbamoyl]phenyl]-2-methyl-benzamide; N-[5-[[2-bromo-6-chloro-4- [1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl] phenyl]carbamoyl]-2-cyan o-phenyl]-4-cyano-2-methyl- benzamide; 2-(1,3-dioxan-2-yl)-6-[2-(3-pyridinyl)-5-thiazolyl]-pyridine; 2-[6-[2-(5-fluoro-3- pyridinyl)-5-thiazolyl]-2-pyridinyl]-pyrimidine; 2-[6-[2-(3-pyridinyl)-5-thiazolyl]-2-pyridinyl]- pyrimidine; N-methylsulfonyl-6-[2-(3-pyridyl)thiazol-5-yl]pyridine-2-carboxamide; N- methylsulfonyl-6-[2-(3-pyridyl)thiazol-5-yl]pyridine-2-carboxamide; N-ethyl-N-[4-methyl-2-(3- pyridyl)thiazol-5-yl]-3-methylthio-propan amide; N-methyl-N-[ 4-methyl-2-( 3-pyridyl)thiazol-5-yl]- 3-methylthio-propanamide;N,2-dimethyl-N-[4-methyl-2-(3-pyridyl)thiazol-5-yl]-3- methylthiopropanamide; N-ethyl-2-methyl-N-[4-methyl-2-(3-pyridyl)thiazol-5-yl]-3-methylthio- propanamide; N-[4-chloro-2-(3-pyridyl)thiazol-5-yl]-N-ethyl-2-methyl-3-methylthio-propanamide; N-[ 4-chloro-2-(3-pyridyl )thiazol-5-yl]-N ,2-dimethyl-3-methylthio-propanamide;N-[4-chloro-2-(3- pyridyl)thiazol-5-yl]-N-methyl-3-methylthio-propanamide; N-[4-chloro-2-(3-pyridyl)thiazol-5-yl]-N- ethyl-3-methylthio-propanamide; 1-[(6-chloro-3-pyridinyl)methyl]-1,2,3,5,6,7-hexahydro-5-methoxy- 7-methyl-8-nitro-imidazo[1,2-a]pyridine;1-[(6-chloropyridin-3-yl)methyl]-7-methyl-8-nitro- 1,2,3,5,6,7-hexahydroimidazo[1,2-a]pyridin-5-ol; 1-isopropyl-N,5-dimethyl-N-pyridazin-4-yl- pyrazole-4-carboxamide;1-(1,2-dimethylpropyl)-N-ethyl-5-methyl-N-pyridazin-4-yl-pyrazole-4- carboxamide; N,5-dimethyl-N-pyridazin-4-yl-1-(2,2,2-trifluoro-1-methy1-ethyl)pyrazole-4- carboxamide; 1-[1-(1-cyanocyclopropyl)ethyl]-N-ethyl-5-methyl-N-pyridazin-4-yl-pyrazole-4- carboxamide; N-ethyl-1-(2-fluoro-1-methyl-propyl)-5-methyl-N-pyridazin-4-yl-pyrazole-4- carboxamide; 1-(1,2-dimethylpropyl)-N,5-dimethyl-N-pyridazin-4-yl-pyrazole-4-carboxamide; 1-[1- (1-cyanocyclopropyl)ethyl]-N,5-dimethyl-N-pyridazin-4-yl-pyrazole-4-carboxamide;N-methyl-1-(2- fluoro-1-methyl-propyl]-5-methyl-N-pyridazin-4-yl-pyrazole-4-carboxamide; 1-(4,4- difluorocyclohexyl)-N-ethyl-5-methyl-N-pyridazin-4-yl-pyrazole-4-carboxamide; 1-(4,4- difluorocyclohexyl)-N,5-dimethyl-N-pyridazin-4-yl-pyrazole-4-carboxamide, N-( 1-methylethyl)-2- (3-pyridinyl)-2H-indazole-4-carboxamide;N-cyclopropyl-2-(3-pyridinyl)-2H-indazole-4- carboxamide; N-cyclohexyl-2-(3-pyridinyl)- 2H-indazole-4-carboxamide; 2-(3-pyridinyl)-N-(2,2,2- trifluoroethyl)-2H-indazole-4-carboxamide; 2-(3-pyridinyl)-N-[(tetrahydro-2-furanyl)methyl]-2H- indazole-5-carboxamide; methyl 2-[[2-(3-pyridinyl)-2H-indazol-5-yl]carbonyl]hydrazinecarboxylate; N-[(2,2-difluorocyclopropyl)methyl]-2-(3-pyridinyl)-2H-indazole-5-carboxamide; N-(2,2- difluoropropyl)-2-(3-pyridinyl)-2H-indazole-5-carboxamide; 2-(3-pyridinyl )N-(2-pyrimidinylmethyl )-2H-indazole-5-carboxamide; N-[(5-methyl-2-pyrazinyl)methyl]-2-(3-pyridinyl)-2H-indazole-5- carboxamide, N-[3-chloro-1-(3-pyridyl)pyrazol-4-yl]N-ethyl-3-(3, 3 ,3-trifluoropropylsulfanyl) propanamide; N-[3-chloro-1-(3-pyridyl)pyrazol-4-yl]-N-ethyl-3-(3,3,3-trifluoropropylsulfinyl) propanamide; N-[3-chloro-1-(3-pyridyl)pyrazol-4-yl]-3-[(2,2-difluorocyclopropyl)methylsulfanyl]-N- ethyl-propanamide; N-[3-chloro-1-(3-pyridyl)pyrazol-4-yl]-3-[(2,2-difluorocyclopropyl) methylsulfinyl]-N-ethyl-propanamide; sarolaner, lotilaner. The active substances referred above, their preparation and their activity e.g. against harmful fungi/insect/nematode is known (cf.: http://www.alanwood.net/pesticides/); these substances are commercially available. The compounds described by IUPAC nomenclature, their preparation and their pesticidal activity are also known (cf. Can. J. Plant Sci.48(6), 587-94, 1968; EP-A 141317; EP- A 152031; EP-A 226917; EP-A 243970; EP-A 256503; EP-A 428941; EP-A 532022; EP-A 1028 125; EP-A1 035 122; EP-A 1 201 648; EP-A 1 122 244, JP 2002316902; DE 19650197; DE 10021412; DE 102005009458; US 3,296,272; US 3,325,503; WO 98/46608; WO 99/14187; WO 99/24413; WO 99/27783; WO 00/29404; WO 00/46148; WO 00/65913; WO 01/54501; WO 01/56358; WO 02/22583; WO 02/40431; WO 03/10149; WO 03/11853; WO 03/14103; WO 03/16286; WO 03/53145; WO 03/61388; WO 03/66609; WO 03/74491; WO 04/49804; WO 04/83193; WO 05/120234; WO 05/123689; WO 05/123690; WO 05/63721; WO 05/87772; WO 05/87773; WO 06/15866; WO 06/87325; WO 06/87343; WO 07/82098; WO 07/90624, WO 10/139271, WO 11/028657, WO 12/168188, WO 07/006670, WO 11/77514; WO 13/047749, WO 10/069882, WO 13/047441, WO 03/16303, WO 09/90181, WO 13/007767, WO 13/010862, WO 13/127704, WO 13/024009, WO 13/24010, WO 13/047441, WO 13/162072, WO 13/092224, WO 11/135833, CN 1907024, CN 1456054, CN 103387541, CN 1309897, WO 12/84812, CN 1907024, WO 09094442, WO 14/60177, WO 13/116251, WO 08/013622, WO 15/65922, WO 94/01546, EP 2865265, WO 07/129454, WO 12/165511, WO 11/081174, WO 13/47441). The mass ratio of any two ingredients in each combination is selected as to give the desired effect, for example, enhanced activity. In general, the mass ratio would vary depending on the specific ingredient and how many ingredients are present in the combination. Generally, the mass ratio between any two ingredients in any combination of the present invention, independently of one another, is from 100:1 to 1:100, including from 99:1, 98:2, 97:3, 96:4, 95:5, 94:6, 93:7, 92:8, 91:9, 90:10, 89:11, 88:12, 87:13, 86:14, 85:15, 84:16, 83:17, 82:18, 81:19, 80:20, 79:21, 78:22, 77:23, 76:24, 75:25, 74:26, 73:27, 72:28, 71:29, 70:30, 69:31, 68:32, 67:33, 66:34, 65:45, 64:46, 63:47, 62:48, 61:49, 60:40, 59:41, 58:42, 57:43, 56:44, 55:45, 54:46, 53:47, 52:48, 51:49, 50:50, 49:51, 48:52, 47:53, 46:54, 45:55, 44:56, 43:57, 42:58, 41:59, 40:60, 39:61, 38:62, 37:63, 36:64, 35:65, 34:66, 33:67, 32:68, 31:69, 30:70, 29:71, 28:72, 27:73, 26:74, 25:75, 24:76, 23:77, 22:78, 21:79, 20:80, 19:81, 18:82, 17:83, 16:84, 15:85, 14:86, 13:87, 12:88, 11:89, 10:90, 9:91, 8:92, 7:93, 6:94, 5:95, 4:96, 3:97, 2:98, to 1:99. Preferred mass ratios between any two components of present invention are from 75:1 to 1:75, more preferably, 50:1 to 1.50, especially 25:1 to 1:25, advantageously 10:1 to 1:10, such as 5:1 to 1:5, for example 1:3 to 3:1. The mixing ratios are understood to include, on the one hand, ratios by mass and also, on other hand, molar ratios. The combinations of the present invention (i.e. those comprising a compound of the present invention and one or more other biological active agents) may be applied simultaneously or sequentially. In the event, the ingredients of a combination are applied sequentially (i.e., one after the other), the ingredients are applied sequentially within a reasonable period of each other to attain the biological performance, such as within a few hours or days. The order of applying the ingredients in the combination, i.e., whether the compounds of formula (I) should be applied first or not is not essential for working the present invention. In the event ingredients of the combinations are applied simultaneously in the present invention, they may be applied as a composition containing the combination, in which case (A) the compound of formula (I) and the one or more other ingredients in the combinations can be obtained from separate formulation sources and mixed together (known as a tank-mix, ready-to-apply, spray broth, or slurry), or (B) the compound of formula (I) and the one or more other ingredients can be obtained as single formulation mixture source (known as a pre-mix, ready-mix, concentrate, or formulated product). In an embodiment, independent of other embodiments, a compound according to the present invention is applied as a combination. Accordingly, the present invention also provides a composition comprising a compound according to the invention as herein described and one or more other biological active agents, and optionally one or more customary formulation auxiliaries; which may be in the form of a tank-mix or pre-mix composition. The compounds of formula (I) are particularly useful for controlling and preventing helminth and nematode endo and ecto-parasitic infestations and infections in warm-blooded animals such as cattle, sheep, swine, camels, deer, horses, poultry, fish, rabbits, goats, mink, fox, chinchillas, dogs and cats as well as humans. In the context of control and prevention of infestation and infections in warm- blooded animals, compounds of invention are especially useful for the control of helminths and nematodes. Examples for helminths are members of the class Trematoda, commonly known as flukes or flatworms, especially members of the genera Fasciola, Fascioloides, Paramphistomu, Dicrocoelium, Eurytrema, Ophisthorchis, Fasciolopsis, Echinostoma and Paragonimus. Nematodes which can be controlled by the formula (I) compounds include the genera Haemonchus, Ostertagia, Cooperia, Oesphagastomu, Nematodirus, Dictyocaulus, Trichuris, Dirofilaria, Ancyclostoma, Ascaria and the like. For oral administration to warm-blooded animals, the compounds of the invention may be formulated as animal feeds, animal feed premixes, animal feed concentrates, pills, solutions, pastes, suspensions, drenches, gels, tablets, boluses and capsules. In addition, the compounds of the invention may be administered to the animals in their drinking water. For oral administration, the dosage form chosen should provide the animal with about 0.01 mg/kg to 100 g/kg of animal body weight per day of the compound of the invention. Alternatively, the compounds of the invention may be administered to animals parenterally, for example, by intraruminal, intramuscular, intravenous or subcutaneous injection. The compounds of the invention may be dispersed or dissolved in a physiologically acceptable carrier for subcutaneous injection. Alternatively, the compounds of the invention may be formulated into an implant for subcutaneous administration. In addition the compounds of the invention may be transdermally administered to animals. For parenteral administration, the dosage form chosen should provide the animal with about 0.01 mg/kg to 100 mg/kg of animal body weight per day of the compound of the invention. The compounds of the invention may also be applied topically to the animals in the form of dips, dusts, powders, collars, medallions, sprays and pour-on formulations. For topical application, dips and sprays usually contain about 0.5 ppm to 5,000 ppm and preferably about 1 ppm to 3,000 ppm of the compound of the invention. In addition, the compounds of the invention may be formulated as ear tags for animals, particularly quadrupeds such as cattle and sheep. In an embodiment, independent of any other embodiments, a compound of formula (I) is an anti- helminth compound. In an embodiment, independent of any other embodiments, a compound of formula (I) is a pesticidal compound, preferably a nematicidal compound. The compounds of the present invention not only control nematode pests effectively but also show positive crop response such as plant growth enhancement effects like enhanced crop vigor, enhanced root growth, enhanced tolerance to drought, high salt, high temperature, chill, frost or light radiation, improved flowering, efficient water & nutrient utilization (such as improved nitrogen assimilation), enhanced quality plant product, more number of productive tillers, enhanced resistance to fungi, insects, pests and the like, which results in higher yields.
CHEMISTRY EXAMPLES: The following examples set forth the manner and process of making compounds of the present invention without being a limitation thereof and include the best mode contemplated by the inventors for carrying out the invention. Example 1: Preparation of 4,4-difluorobut-3-en-1-yl 2-(4-chloro-1H-pyrazol-1-yl)acetate
Figure imgf000036_0001
To a solution of 2-(4-chloro-1H-pyrazol-1-yl)acetic acid (250 mg, 1.56 mmol) in dry N,N- dimethylformamide (8 mL), N,N-diisopropylethylamine (0.27 ml, 1.56 mmol) and 4-bromo-1,1- difluorobut-1-ene (532 mg, 3.11 mmol) were added, and the reaction mixture was stirred at 80 ℃ for 16 h. Afterwards it was diluted with ethyl acetate (30 mL) and water (30 mL), the organic layer was separated and the aqueous layer was extracted again with ethyl acetate (30 mL). The combined organic layers were dried over anhydrous sodium sulphate, filtered and concentrated under reduced pressure to obtain a crude product. The crude product was purified by column chromatography using ethyl acetate/hexane as eluant system to obtain the title compound 4,4-difluorobut-3-en-1-yl 2-(4- chloro-1H-pyrazol-1-yl)acetate (270 mg, 1.077 mmol, 69.2 % yield), LCMS (M+1): 251 Example 2: Preparation of 3,4,4-trifluorobut-3-en-1-yl 2-(4-methyl-1H-pyrazol-1-yl)acetate
Figure imgf000036_0002
To a solution of 2-(4-methyl-1H-pyrazol-1-yl)acetic acid (450 mg, 3.21 mmol) in dry N,N- dimethylformamide (8 mL), N,N-diisopropylethylamine (0.561 ml, 3.21 mmol) and 4-chloro-1,1,2- trifluorobut-1-ene (928 mg, 6.42 mmol) were added and the reaction mixture was stirred at 80 ℃ for 16 h. The reaction mixture was diluted with ethyl acetate (30 mL) and water (30 mL), the organic layer was separated, and the aqueous layer was extracted again with ethyl acetate (30 mL). The combined organic layers were dried over anhydrous sodium sulphate, filtered and concentrated under reduced pressure to obtain a crude product. The crude product was purified by column chromatography using ethyl acetate/hexane as eluant system to obtain the title compound 3,4,4- trifluorobut-3-en-1-yl 2-(4-methyl-1H-pyrazol-1-yl)acetate (375 mg, 1.51 mmol, 47.1 % yield), LCMS (M+1): 249.1 Example 3: Preparation of 3,4,4-trifluorobut-3-en-1-yl 2-(3,5-dimethyl-1H-pyrazol-1-yl)acetate
Figure imgf000036_0003
To a solution of 2-(3,5-dimethyl-1H-pyrazol-1-yl)acetic acid (450 mg, 2.92 mmol) in dry N,N- dimethylformamide (8 mL), N,N-diisopropylethylamine (0.510 ml, 2.92 mmol) and 4-chloro-1,1,2- trifluorobut-1-ene (844 mg, 5.84 mmol) were added and the reaction mixture was stirred at 80 ℃ for 16 h. The reaction mixture was diluted with ethyl acetate (30 mL) and water (30 mL), the organic layer was separated and the aqueous layer was extracted again with ethyl acetate (30 mL). The combined organic layers were dried over anhydrous sodium sulphate, filtered and concentrated under reduced pressure to obtain a crude product. The crude product was purified by column chromatography using ethyl acetate/hexane as eluant system to obtain the title compound 3,4,4- trifluorobut-3-en-1-yl 2-(3,5-dimethyl-1H-pyrazol-1-yl)acetate (340 mg, 1.297 mmol, 44.4 % yield), LCMS (M+1): 263.1 Example 4: Preparation of 3,4,4-trifluorobut-3-en-1-yl 2-(4-chloro-1H-pyrazol-1-yl)propanoate
Figure imgf000037_0001
Step 1: Preparation of ethyl 2-(4-chloro-1H-pyrazol-1-yl)propanoate To a solution of 4-chloro-1H-pyrazole (500 mg, 4.88 mmol) in dry N,N-Dimethylformamide (10 mL), potassium carbonate (1.35 g, 9.75 mmol) and ethyl 2-bromopropanoate (0.9 ml, 6.4 mmol) were added and the reaction mixture was stirred at 60 ℃ for 4 h. The reaction mixture was diluted with ethyl acetate (30 mL) and water (30 mL), the organic layer was separated and the aqueous layer was extracted again with ethyl acetate (30 mL). The combined organic layers were dried over anhydrous sodium sulphate, filtered and concentrated under reduced pressure to obtain a crude product. The crude product was purified by column chromatography using ethyl acetate/hexane as eluant system to obtain the title compound ethyl 2-(4-chloro-1H-pyrazol-1-yl)propanoate (600 mg, 2.96 mmol, 60.7 % yield), LCMS (M+1): 203.1 Step 2: Preparation of 2-(4-chloro-1H-pyrazol-1-yl)propanoic acid To a solution of 2-(4-chloro-1H-pyrazol-1-yl)propanoate (1 g, 4.93 mmol) in methanol- tetrahydrofuran (6 ml:3 ml), lithium hydroxide (0.236 g, 9.87 mmol) in water (1 ml) was added and the resulting mixture was stirred at room temperature for 2 h. The reaction mixture was concentrated, diluted with water (5 ml) and washed with ethyl acetate. The aqeoues layer was acidified with conc. hydrochloric acid and extracted with ethyl acetate (60ml x 2). The combined organic layers were dried over anhydrous sodium sulphate, filtered and concentrated under reduced pressure to obtain the desire product, 2-(4-chloro-1H-pyrazol-1-yl)propanoic acid (600 mg, 3.44 mmol, 69.6 % yield), LCMS (M+1): 174.9 Step 3: Preparation of 3,4,4-trifluorobut-3-en-1-yl 2-(4-chloro-1H-pyrazol-1-yl)propanoate To a solution of 2-(4-chloro-1H-pyrazol-1-yl)propanoic acid (400 mg, 2.291 mmol) in dry N,N- dimethylformamide (8 mL), N,N-diisopropylethylamine (0.8 ml, 4.58 mmol) and 4-chloro-1,1,2- trifluorobut-1-ene (662 mg, 4.58 mmol) were added and the reaction mixture was stirred at 80 ℃ for 16 h. The reaction mixture was diluted with ethyl acetate (30 mL) and water (30 mL), the organic layer was separated and the aqueous layer was extracted again with ethyl acetate (30 mL). The combined organic layers were dried over anhydrous sodium sulphate, filtered and concentrated under reduced pressure to obtain a crude product. The crude product was purified by column chromatography using ethyl acetate/hexane as eluant system to obtain the title compound 3,4,4- trifluorobut-3-en-1-yl 3,4,4-trifluorobut-3-en-1-yl 2-(4-chloro-1H-pyrazol-1-yl)propanoate (500 mg, 1.77 mmol, 77 % yield), LCMS (M+1): 282.95 Example 5: Preparation of 3,4,4-trifluorobut-3-en-1-yl 2-(4-chloro-1H-pyrazol-1-yl)-2- methylpropanoate
Figure imgf000038_0001
Step 1: Preparation of ethyl 2-(4-chloro-1H-pyrazol-1-yl)-2-methylpropanoate To a solution of 4-chloro-1H-pyrazole (500 mg, 4.88 mmol) in dry N,N-dimethylformamide (10 mL), cesium carbonate (9.53 g, 29.3 mmol) and ethyl 2-bromo-2-methylpropanoate (2.85 ml, 19.02 mmol) were added, and the reaction mixture was stirred at 60 ℃ for 4 h. The reaction mixture was diluted with ethyl acetate (30 mL) and water (30 mL), the organic layer was separated and the aqueous layer was extracted again with ethyl acetate (30 mL). The combined organic layers were dried over anhydrous sodium sulphate, filtered and concentrated under reduced pressure to obtain a crude product. The crude product was purified by column chromatography using ethyl acetate/hexane as eluant system to obtain the title compound ethyl 2-(4-chloro-1H-pyrazol-1-yl)-2-methylpropanoate (2.5 g, 11.54 mmol, 79 % yield), LCMS (M+1): 217.1 Step 2: Preparation of 2-(4-chloro-1H-pyrazol-1-yl)-2-methylpropanoic acid To a solution of ethyl 2-(4-chloro-1H-pyrazol-1-yl)-2-methylpropanoate (3 g, 13.85 mmol) in methanol-Tetrahydrofuran (6 ml:3 ml), lithium hydroxide (0.66 g, 27.7 mmol) in water (1 ml) was added, and the resulting mixture was stirred at room temperature for 2 h. The reaction mixture was concentrated, diluted with water (5 ml), washed with ethyl acetate The aqeoues layer was acidified with conc. hydrochloric acid and extracted with ethyl acetate. The combined organic layers were dried over anhydrous sodium sulphate, filtered and concentrated under reduced pressure to obtain the desire product, 2-(4-chloro-1H-pyrazol-1-yl)-2-methylpropanoic acid (2 g, 10.6 mmol, 77 % yield), LCMS (M+1): 189.1 Step 3: Preparation of 3,4,4-trifluorobut-3-en-1-yl 2-(4-chloro-1H-pyrazol-1-yl)-2- methylpropanoate To a solution of 2-(4-chloro-1H-pyrazol-1-yl)-2-methylpropanoic acid (300 mg, 1.59 mmol) in dry N,N-dimethylformamide (8 mL), N,N-diisopropylethylamine (0.6 ml, 3.2 mmol) and 4-chloro-1,1,2- trifluorobut-1-ene (460 mg, 3.18 mmol) were added, and the reaction mixture was stirred at 80 ℃ for 16 h. The reaction mixture was diluted with ethyl acetate (30 mL) and water (30 mL), the organic layer was separated and the aqueous layer was extracted again with ethyl acetate (30 mL). The combined organic layer was dried over anhydrous sodium sulphate, filtered and concentrated under reduced pressure to obtain a crude product. The crude product was purified by column chromatography using 1 - 30% ethyl acetate/hexane to obtain the title compound 3,4,4-trifluorobut-3- en-1-yl 2-(4-chloro-1H-pyrazol-1-yl)-2-methylpropanoate (420 mg, 1.42 mmol, 89 % yield), LCMS (M+1): 296.95 Example 6: Preparation of 3,4,4-trifluorobut-3-en-1-yl 2-(4-methyl-1H-pyrazol-1-yl)propanoate
Figure imgf000039_0001
Step 1: Preparation of ethyl 2-(4-methyl-1H-pyrazol-1-yl)propanoate To a solution of 4-methyl-1H-pyrazole (1.5 g, 18.27 mmol) in dry N,N-dimethylformamide (10 mL), potassium carbonate (5.05 g, 36.5 mmol) and ethyl 2-bromopropanoate (3.31 ml, 23.75 mmol) were added, and the reaction mixture was stirred at 60 ℃ for 4 h. The reaction mixture was diluted with ethyl acetate (30 mL) and water (30 mL), the organic layer was separated and the aqueous layer was extracted again with ethyl acetate (30 mL). The combined organic layers were dried over anhydrous sodium sulphate, filtered and concentrated under reduced pressure to obtain a crude product. The crude product was purified by column chromatography using ethyl acetate/hexane as eluant system to obtain the title compound ethyl 2-(4-chloro-1H-pyrazol-1-yl)-2-methylpropanoate (2.5 g, 11.54 mmol, 79 % yield), LCMS (M+1): 217.1 Step 2: Preparation of 2-(4-methyl-1H-pyrazol-1-yl)propanoic acid To a solution of ethyl 2-(4-methyl-1H-pyrazol-1-yl)propanoate (2.2 g, 12.07 mmol) in methanol- tetrahydrofuran (6 ml:3 ml), lithium hydroxide (0.58 g, 24.2 mmol) in water (1 ml) was added and the resulting mixture was stirred at room temperature for 2 h. The reaction mixture was concentrated, diluted with water (5 ml), washed with ethyl acetate. The aqeoues layer was acidified with conc. hydrochloric acid and extracted with ethyl acetate. The combined organic layers were dried over anhydrous sodium sulphate, filtered and concentrated under reduced pressure to obtain the desire product, 2-(4-methyl-1H-pyrazol-1-yl)propanoic acid (1.5 g, 9.73 mmol, 81 % yield), LCMS (M+1): 155.1 Step 3: Preparation of 3,4,4-trifluorobut-3-en-1-yl 2-(4-methyl-1H-pyrazol-1-yl)propanoate To a solution of 2-(4-methyl-1H-pyrazol-1-yl)propanoic acid (300 mg, 1.95 mmol) in dry N,N- dimethylformamide (8 mL), N,N-diisopropylethylamine (0.68 ml, 3.89 mmol) and 4-chloro-1,1,2- trifluorobut-1-ene (366 mg, 2.53 mmol) were added, and the reaction mixture was stirred at 80 ℃ for 16 h. The reaction mixture was diluted with ethyl acetate (30 mL) and water (30 mL), the organic layer was separated and the aqueous layer was extracted again with ethyl acetate (30 mL). The combined organic layers were dried over anhydrous sodium sulphate, filtered and concentrated under reduced pressure to obtain a crude product. The crude product was purified by column chromatography using ethyl acetate/hexane as eluant system to obtain the title compound 3,4,4- trifluorobut-3-en-1-yl 2-(4-methyl-1H-pyrazol-1-yl)propanoate (345 mg, 1.32 mmol, 67.6 % yield), LCMS (M+1): 263.1 Example 7: Preparation of 3,4,4-trifluorobut-3-en-1-yl 2-methyl-2-(4-methyl-1H-pyrazol-1- yl)propanoate
Figure imgf000040_0001
Step 1: Preparation of ethyl 2-methyl-2-(4-methyl-1H-pyrazol-1-yl)propanoate To a solution of 4-methyl-1H-pyrazole (1.5 g, 18.27 mmol) in dry N,N-Dimethylformamide (10 mL), cesium carbonate (8.93 g, 27.4 mmol) and ethyl 2-bromo-2-methylpropanoate (4.63 g, 23.75 mmol) were added, and the reaction mixture was stirred at 60 ℃ for 4 h. The reaction mixture was diluted with ethyl acetate (30 mL) and water (30 mL), the organic layer was separated and the aqueous layer was extracted again with ethyl acetate (30 mL). The combined organic layers were dried over anhydrous sodium sulphate, filtered and concentrated under reduced pressure to obtain a crude product. The crude product was purified by column chromatography using ethyl acetate/hexane as eluant system to obtain the title compound ethyl 2-methyl-2-(4-methyl-1H-pyrazol-1-yl)propanoate (2.1 g, 10.70 mmol, 58.6 % yield) LCMS (M+1): 197.1 Step 2: Preparation of 2-methyl-2-(4-methyl-1H-pyrazol-1-yl)propanoic acid To a solution of ethyl 2-methyl-2-(4-methyl-1H-pyrazol-1-yl)propanoate (2.5 g, 12.74 mmol) in methanol-tetrahydrofuran (6 ml:3 ml), lithium hydroxide (0.61 g, 25.5 mmol) in water (1 ml) was added and the resulting mixture was stirred at room temperature for 2 h. The reaction mixture was concentrated, diluted with water (5 ml), washed with ethyl acetate. The aqeoues layer was acidified with conc. hydrochloric acid and extracted with ethyl acetate. The combined organic layers were dried over anhydrous sodium sulphate, filtered and concentrated under reduced pressure to obtain the desire product, 2-methyl-2-(4-methyl-1H-pyrazol-1-yl)propanoic acid (1.8 g, 10.7 mmol, 84 % yield), LCMS (M+1): 169.1 Step 3: 3,4,4-trifluorobut-3-en-1-yl 2-methyl-2-(4-methyl-1H-pyrazol-1-yl)propanoate To a solution of 2-methyl-2-(4-methyl-1H-pyrazol-1-yl)propanoic acid (600 mg, 3.57 mmol) in dry N,N-dimethylformamide (8 mL), N,N-diisopropylethylamine (1.2 ml, 7.13 mmol) and 4-chloro-1,1,2- trifluorobut-1-ene (670 mg, 4.64 mmol) were added and the reaction mixture was stirred at 80 ℃ for 16 h. The reaction mixture was diluted with ethyl acetate (30 mL) and water (30 mL), the organic layer was separated and the aqueous layer was extracted again with ethyl acetate (30 mL). The combined organic layers were dried over anhydrous sodium sulphate, filtered and concentrated under reduced pressure to obtain a crude product. The crude product was purified by column chromatography using ethyl acetate/hexane as eluant system to obtain the title compound 4,4- difluorobut-3-en-1-yl 3,4,4-trifluorobut-3-en-1-yl 2-methyl-2-(4-methyl-1H-pyrazol-1-yl)propanoate (350 mg, 1.267 mmol, 35.5 % yield), LCMS (M+1): 277.1 Example 8: Preparation of 3,4,4-trifluorobut-3-en-1-yl 2-(3-methyl-1H-indazol-1-yl)acetate Step 1: Preparation of ethyl 2-(3-methyl-1H-indazol-1-yl)acetate To a solution of 3-methyl-2H-indazole (400 mg, 3.03 mmol) in dry acetone (8 mL), potassium carbonate (837 mg, 6.05 mmol) and ethyl 2-bromoacetate (505 mg, 3.03 mmol) were added, and the reaction mixture was stirred at 60 ℃ for 4 h. The reaction mixture was diluted with ethyl acetate (30 mL) and water (30 mL), the organic layer was separated and the aqueous layer was extracted again with ethyl acetate (30 mL). The combined organic layers were dried over anhydrous sodium sulphate, filtered and concentrated under reduced pressure to obtain a crude product. The crude product was purified by column chromatography using ethyl acetate/hexane as eluant system to obtain the title compound ethyl 2-(3-methyl-1H-indazol-1-yl)acetate (500 mg, 2.3 mmol, 76 % yield) LCMS (M+1): 219.1 Step 2: Preparation of 2-(3-methyl-1H-indazol-1-yl)acetic acid To a solution of ethyl 2-(3-methyl-1H-indazol-1-yl)acetate (590 mg, 2.70 mmol) in methanol- tetrahydrofuran (4 ml:2 ml), lithium hydroxide (129 mg, 5.41 mmol) in water (0.5 ml) was added, and the resulting mixture was stirred at room temperature for 2 h. The reaction mixture was concentrated, diluted with water (5 ml), washed with ethyl acetate. The aqeoues layer was acidified with conc. hydrochloric acid and extracted with ethyl acetate. The combined organic layers were dried over anhydrous sodium sulphate, filtered and concentrated under reduced pressure to obtain the desire product, 2-(3-methyl-1H-indazol-1-yl)acetic acid (450 mg, 2.37 mmol, 88 % yield), LCMS (M+1): 191.1 Step 3: Preparation of 3,4,4-trifluorobut-3-en-1-yl 2-(3-methyl-1H-indazol-1-yl)acetate To a solution of 2-(3-methyl-2H-indazol-2-yl)acetic acid (250 mg, 1.314 mmol) in dry N,N- dimethylformamide (7 mL), N,N-diisopropylethylamine (0.46 ml, 2.63 mmol) and 4-chloro-1,1,2- trifluorobut-1-ene (247 mg, 1.71 mmol) were added, and the reaction mixture was stirred at 80 ℃ for 16 h. The reaction mixture was diluted with ethyl acetate (30 mL) and water (30 mL), the organic layer was separated and the aqueous layer was extracted again with ethyl acetate (30 mL). The combined organic layers were dried over anhydrous sodium sulphate, filtered and concentrated under reduced pressure to obtain a crude product. The crude product was purified by column chromatography using ethyl acetate/hexane as eluant system to obtain the title compound 3,4,4- trifluorobut-3-en-1-yl 2-(3-methyl-2H-indazol-2-yl)acetate (160 mg, 0.54 mmol, 40 % yield), LCMS (M+1): 299.3 Example 9: Preparation of 3,4,4-trifluorobut-3-en-1-yl 2-(4,5-dichloro-1H-imidazol-1-yl)acetate Step 1: Preparation of 2-(4,5-dichloro-1H-imidazol-1-yl)acetic acid To a solution of 4,5-dichloro-1H-imidazole (1 g, 7.30 mmol) in dry acetonitrile (20 ml), potassium carbonate (1.514 g, 10.95 mmol) and tert-butyl 2-bromoacetate (1.295 ml, 8.76 mmol) were added, and the reaction mixture was stirred at room temperature for 2 h. The reaction mixture was diluted with ethyl acetate (30 mL) and water (30 mL), the organic layer was separated and the aqueous layer was extracted again with ethyl acetate (30 mL). The combined organic layers were dried over anhydrous sodium sulphate, filtered and concentrated under reduced pressure to obtain a crude product, tert-butyl 2-(4,5-dichloro-1H-imidazol-1-yl)acetate (1.8 g, 7.17 mmol, 98 % yield). To a stirred solution of tert-butyl 2-(4,5-dichloro-1H-imidazol-1-yl)acetate (1.8 g, 7.17 mmol) in dichloromethane (10 ml) was added hydrochloric acid (7.17 ml, 28.7 mmol) and stirred at 20-25 °C for 16h. The reaction mixutre was evaporated to dryness to afford desired product 2-(4,5-dichloro- 1H-imidazol-1-yl)acetic acid, 1.5 gm as an off-white solid (HCl salt). LCMS (M+1): 194.80; 1HNMR: 1H-NMR (400 MHz, DMSO-d6 ) δ 9.57-9.79 (br s, 1H), 7.78 (s, 1H), 4.87 (s, 2H) Step 2: Preparation of 3,4,4-trifluorobut-3-en-1-yl 2-(4,5-dichloro-1H-imidazol-1-yl)acetate To a solution of 2-(4,5-dichloro-1H-imidazol-1-yl)acetic acid (1.5 g, 7.69 mmol) in dry N,N- dimethylformamide (10 mL), N,N-diisopropylethylamine (4.03 ml, 23.1 mmol) and 4-chloro-1,1,2- trifluorobut-1-ene (247 mg, 1.71 mmol) were added, and the reaction mixture was stirred at 80 ℃ for 16 h. The reaction mixture was diluted with ethyl acetate (30 mL) and water (30 mL), the organic layer was separated and the aqueous layer was extracted again with ethyl acetate (30 mL). The combined organic layers were dried over anhydrous sodium sulphate, filtered and concentrated under reduced pressure to obtain a crude product. The crude product was purified by column chromatography using ethyl acetate/hexane as eluant system to obtain the title compound 3,4,4- trifluorobut-3-en-1-yl 2-(4,5-dichloro-1H-imidazol-1-yl)acetate (1.1 g, 3.63 mmol, 47.2 % yield) as thick brown oil, LCMS (M-1): 302.85 Example 10: Preparation of 3,4,4-trifluorobut-3-en-1-yl 2-(3,5-dimethyl-1H-1,2,4-triazol-1- yl)acetate To a solution of 2-(3,5-dimethyl-1H-1,2,4-triazol-1-yl)acetic acid (300 mg, 1.94 mmol) in dry N,N- dimethylformamide (05 mL), N,N-diisopropylethylamine (1.013 ml, 5.80 mmol) and 4-chloro-1,1,2- trifluorobut-1-ene (419 mg, 2.90 mmol) were added, and the reaction mixture was stirred at 80 ℃ for 12 h. The reaction mixture was diluted with ethyl acetate (30 mL) and water (30 mL), the organic layer was separated and the aqueous layer was extracted again with ethyl acetate (30 mL). The combined organic layers were dried over anhydrous sodium sulphate, filtered and concentrated under reduced pressure to obtain a crude product. The crude product was purified by column chromatography using methanol/dichloromethane as eluant system to obtain the title compound, 3,4,4-trifluorobut-3-en-1-yl 2-(3,5-dimethyl-1H-1,2,4-triazol-1-yl)acetate, LCMS (M+1): 263.9 Example 11: Preparation of 2-(4-chloro-1H-pyrazol-1-yl)-N-(3,4,4-trifluorobut-3-en-1- yl)acetamide To a stirred solution of 2-(4-chloro-1H-pyrazol-1-yl)acetic acid (0.179 g, 1.114 mmol) in N,N- dimethylformamide (3 ml) was added 3,4,4-trifluorobut-3-en-1-amine hydrochloride (0.150g, 0.928 mmol) and N,N-diisopropylethylamine (0.487 ml, 2.79 mmol) followed by the addition of HATU (0.530 g, 1.393 mmol. The resukting reaction mixture was stirred at 25 °C for 3h. The reaction mixture was then diluted with water and extracted with ethyl acetate (25ml x 2). The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure to dryness to obtain a crude product. The crude product was purified by column chromatography using ethyl acetate/hexane as eluant system to obtain the title compound 2-(4-chloro-1H-pyrazol-1-yl)-N-(3,4,4- trifluorobut-3-en-1-yl)acetamide (170mg, 0.635 mmol, 68.4 % yield) as colorless oil. LCMS (M+1): 267.8 Table 1 Representative compounds of the present disclosure prepared according to the suitable methods as described in schemes and examples Table-1:
Figure imgf000043_0001
Figure imgf000044_0001
Figure imgf000045_0001
Figure imgf000046_0001
Figure imgf000047_0001
Figure imgf000048_0001
Figure imgf000049_0001
Figure imgf000050_0001
Figure imgf000051_0001
Figure imgf000052_0001
* Compound names generated using Chemdraw Professional 19.1 As described herein the compounds of formula (I) show high nematicidal activity which is exerted with respect to nematodes which attack on important agricultural crops. The compounds of the present invention were assessed for their activity against one or more of the following nematodes. Biological examples Biological Test Examples for Plant parasitic nematodes Example 1: Meloidogyne incognita (Root-knot nematode): IN VITRO TEST Meloidogyne incognita: The test compounds, at a concentration of 300 ppm, were pipetted into the wells of a 24-well microtiter plate containing, per well, 500 μL of distilled water with 50 Meloidogyne incognita juveniles. The suspension was lightly shaken for uniform mixing of compounds. The test plates were covered with lids, and were incubated at 25 °C temperature and 90% RH. Dead/inactive nematodes were counted at an interval of 48, 72 and 96 hours under a microscope and the percent mortality was calculated by comparing the result of the treatment with the one of the untreated control. Compounds 8 17 25 35 36 37 44 47 55 56 57 58 61 62 63 64 65 66 67 68 69 70 74 75 at 300ppm showed more than 70% mortality in the tests, where there was no mortality in the untreated check. Meloidogyne incognita: IN VIVO TEST Cucumber plants were grown in seedling trays containing a mixture of Sand:Soil:FYM:Cocopeat in ratio of 1:1:1:1. One mL of test compounds at the desired test concentrations was applied into the soil with the help of a micropipette when the cucumber seedlings were ten days old. After the application the seedlings were inoculated with approximately 2000 freshly hatched second-stage juveniles of Meloidogyne incognita. The treated plants were allowed to grow at 27 °C temperature under greenhouse conditions. Observation of gall rating was recorded 15 days after the application. Plants were carefully uprooted and roots were washed thoroughly. The gall rating was observed on 0-10 scale as described by Zeck (1971) as mentioned below: 0 = no galls 1 = very few small galls 2 = numerous small galls 3 = numerous small galls of which some are grown together 4 = numerous small and some big galls 5 = 25% of roots severely galled 6 = 50% of roots severely galled 7 = 75% of roots severely galled 8 = no healthy roots but plant is still green 9 = roots rotting and plant dying 10 = plant and roots dead Compounds 3 4 5 6 7 8 9 10 11 12 16 17 18 20 24 25 26 35 36 38 44 47 48 54 55 56 61 63 64 66 67 68 69 70 75 at 300 ppm recorded less than 3 gall rating in the tests, where there was extensive galling (up to 8) in the untreated check. Further, Table: A indicates the results relating to the effectiveness of compounds of present invention comparative to the compounds known in prior art.
Figure imgf000053_0001
Figure imgf000054_0001
Having described the invention with reference to certain preferred aspects, other aspects will become apparent to one skilled in the art from consideration of the specification. It will be apparent to those skilled in the art that many modifications, both to materials and methods, may be practiced without departing from the scope of the invention.

Claims

CLAIMS: 1. A compound of general formula (I);
Figure imgf000055_0001
wherein, Y represents O or NR5; R1 is selected from the group consisting of hydrogen and F; R2 and R3 are independently selected from the group consisting of hydrogen and C1-C3-alkyl; ring A represents ring system selected from A1 to A12 wherein A may be optionally substituted with one or more R4;
Figure imgf000055_0002
R4 is selected from the group consisting of X, CN, (C=O)-R6, OR5, N(R5)2, S(O)nR6, C1-C6- alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-haloalkyl, C3-C12-cycloalkyl, C3- C10-halocycloalkyl, C3-C6-cycloalkyl-C1-C6-alkyl, phenyl, and C3-C6-heterocyclyl; each group of R4 may be optionally substituted by one or more groups selected from the group consisting of halogen, R5a, OR5a, SR5a, N(R5a)2, Si(R5a)3, COOR5a, CN, and CON(R5a)2; R5 is selected from the group consisting of hydrogen, C1-C4-alkyl, C3-C6-cycloalkyl and C3-C6- cycloalkyl-C1-C3-alkyl; R5a is selected from the group consisting of hydrogen, C1-C6-alkyl and C3-C6-cycloalkyl; R6 is selected from the group consisting of N(R5a)2, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-haloalkyl, C2-C6-haloalkenyl, C2-C6-haloalkynyl and C3-C6-cycloalkyl; R1, R2, R3, R4, R5, R5a and R6 may optinally be substituted with one or more groups consisting of X, CN, C1-C4-alkyl, O-C1-C4-alkyl, S(O)n-C1-C4-alkyl and C3-C6-cycloalkyl; X represent halogen; n represents integers wherein n=0,1 and 2; and/or stereoisomer or agriculturally acceptable salts or tautomers or N-oxides thereof. 2. The compound of formula (I) as claimed in claim 1, wherein; Y represent O; ring A represents ring system selected from A1 to A7 wherein A may be optionally substituted with one or more R4;
Figure imgf000056_0001
Figure imgf000056_0002
R4 is selected from the group consisting of X, CN, C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-haloalkyl, C3-C12-cycloalkyl, C3-C10-halocycloalkyl, C3-C6-cycloalkyl-C1- C6-alkyl, phenyl, and C3-C6-heterocyclyl; each group of R4 may be optionally substituted by one or more groups selected from the group consisting of halogen, R5a, OR5a, SR5a, N(R5a)2, Si(R5a)3, COOR5a, CN, and CON(R5a)2; and/or stereoisomer or agriculturally acceptable salts or tautomers or N-oxides thereof. 3. The compound formula (I) as claimed in claim 1, wherein; Y represent O; ring A represents ring system selected from A8 to A12 wherein A may be optionally substituted with one or more R4;
Figure imgf000056_0003
R4 is selected from the group consisting of X, CN, C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-haloalkyl, C3-C12-cycloalkyl, C3-C10-halocycloalkyl, C3-C6-cycloalkyl-C1- C6-alkyl, phenyl, and C3-C6-heterocyclyl; each group of R4 may be optionally substituted by one or more groups selected from the group consisting of halogen, R5a, OR5a, SR5a, N(R5a)2, Si(R5a)3, COOR5a, CN, and CON(R5a)2; and/or stereoisomer or agriculturally acceptable salts or tautomers or N-oxides thereof. 4. The compound of formula (I) as claimed in claim 1, wherein; ring A represents ring system selected from A1, A2, A6 and A7 wherein A may be optionally substituted with one or more R4;
Figure imgf000057_0001
and/or stereoisomer or agriculturally acceptable salts or tautomers or N-oxides thereof. 5. The compound formula (I) as claimed in claim 1, wherein; Y represent O; ring A represents ring system selected from A1 to A12 wherein A may be optionally substituted with one or more R4; and R4 is selected from the group consisting of X, CN, C1-C6-alkyl, C1-C6-haloalkyl, R5aC=NOR5a, -C1-C6-alkyl-OR5. 6. The compound as claimed in claim 1, wherein said compound of formula (I) is selected from (4,4-difluorobut-3-en-1-yl 2-(5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl)acetate; 4,4-difluorobut- 3-en-1-yl 2-(3,5-bis(trifluoromethyl)-1H-pyrazol-1-yl)acetate; 4,4-difluorobut-3-en-1-yl 2-(3,5- dimethyl-1H-pyrazol-1-yl)acetate; 4,4-difluorobut-3-en-1-yl 2-(4-methyl-1H-pyrazol-1-yl)acetate; 4,4-difluorobut-3-en-1-yl 2-(3,5-bis(difluoromethyl)-1H-pyrazol-1-yl)acetate; 3,4,4-trifluorobut-3-en- 1-yl 2-(5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl)acetate; 4,4-difluorobut-3-en-1-yl 2-(5- cyclopropyl-3-(trifluoromethyl)-1H-pyrazol-1-yl)acetate; 4,4-difluorobut-3-en-1-yl 2-(4-chloro-1H- pyrazol-1-yl)acetate; 3,4,4-trifluorobut-3-en-1-yl 2-(5-cyclopropyl-3-(trifluoromethyl)-1H-pyrazol-1- yl)acetate; 3,4,4-trifluorobut-3-en-1-yl 2-(4-chloro-1H-pyrazol-1-yl)acetate; 3,4,4-trifluorobut-3-en-1- yl 2-(3,5-dimethyl-1H-pyrazol-1-yl)acetate; 3,4,4-trifluorobut-3-en-1-yl 2-(4-methyl-1H-pyrazol-1- yl)acetate; 3,4,4-trifluorobut-3-en-1-yl 2-(3,5-bis(trifluoromethyl)-1H-pyrazol-1-yl)acetate; 4,4- difluorobut-3-en-1-yl 2-(1H-indazol-1-yl)acetate; 3,4,4-trifluorobut-3-en-1-yl 2-(1H-indazol-1- yl)acetate; 3,4,4-trifluorobut-3-en-1-yl 2-(4-chloro-1H-pyrazol-1-yl)propanoate; 4,4-difluorobut-3-en- 1-yl 2-(4-chloro-1H-pyrazol-1-yl)propanoate; 3,4,4-trifluorobut-3-en-1-yl 2-(4-chloro-1H-pyrazol-1- yl)-2-methylpropanoate; 4,4-difluorobut-3-en-1-yl 2-(4-chloro-1H-pyrazol-1-yl)-2-methylpropanoate; 3,4,4-trifluorobut-3-en-1-yl 2-(4-chloro-3,5-dimethyl-1H-pyrazol-1-yl)acetate; 4,4-difluorobut-3-en- 1-yl 2-(4-chloro-3,5-dimethyl-1H-pyrazol-1-yl)acetate; 3,4,4-trifluorobut-3-en-1-yl 2-(3,5-diphenyl- 1H-pyrazol-1-yl)propanoate; 4,4-difluorobut-3-en-1-yl 2-(3,5-diphenyl-1H-pyrazol-1-yl)propanoate; 3,4,4-trifluorobut-3-en-1-yl 2-(4-methyl-1H-pyrazol-1-yl)propanoate; 4,4-difluorobut-3-en-1-yl 2-(4- methyl-1H-pyrazol-1-yl)propanoate; 3,4,4-trifluorobut-3-en-1-yl 2-methyl-2-(4-methyl-1H-pyrazol-1- yl)propanoate; 4,4-difluorobut-3-en-1-yl 2-methyl-2-(4-methyl-1H-pyrazol-1-yl)propanoate; 3,4,4- trifluorobut-3-en-1-yl 2-(3,5-diphenyl-1H-pyrazol-1-yl)acetate; 4,4-difluorobut-3-en-1-yl 2-(3,5- diphenyl-1H-pyrazol-1-yl)acetate; 3,4,4-trifluorobut-3-en-1-yl 2-(3-(difluoromethyl)-2H-indazol-2- yl)acetate; 3,4,4-trifluorobut-3-en-1-yl 2-(3-methyl-2H-indazol-2-yl)acetate; 4,4-difluorobut-3-en-1-yl 2-(3-methyl-1H-indazol-1-yl)acetate; 4,4-difluorobut-3-en-1-yl 2-(3-(difluoromethyl)-2H-indazol-2- yl)acetate; 3,4,4-trifluorobut-3-en-1-yl 2-(3,5-bis(difluoromethyl)-1H-pyrazol-1-yl)acetate; 3,4,4- trifluorobut-3-en-1-yl 2-(1H-pyrazol-1-yl)acetate; 4,4-difluorobut-3-en-1-yl 2-(1H-pyrazol-1- yl)acetate; 3,4,4-trifluorobut-3-en-1-yl 2-(3-(trifluoromethyl)-1H-pyrazol-1-yl)acetate; 4,4- difluorobut-3-en-1-yl 2-(3-(trifluoromethyl)-1H-pyrazol-1-yl)acetate; 3,4,4-trifluorobut-3-en-1-yl 2- (5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl)propanoate; 4,4-difluorobut-3-en-1-yl 2-(5-methyl-3- (trifluoromethyl)-1H-pyrazol-1-yl)propanoate; 3,4,4-trifluorobut-3-en-1-yl 2-methyl-2-(5-methyl-3- (trifluoromethyl)-1H-pyrazol-1-yl)propanoate; 4,4-difluorobut-3-en-1-yl 2-methyl-2-(5-methyl-3- (trifluoromethyl)-1H-pyrazol-1-yl)propanoate; 3,4,4-trifluorobut-3-en-1-yl 2-(2H-indazol-2- yl)acetate; 4,4-difluorobut-3-en-1-yl 2-(2H-indazol-2-yl)acetate; 3,4,4-trifluorobut-3-en-1-yl 2-(3,5- dimethyl-1H-1,2,4-triazol-1-yl)acetate; 2-(4-chloro-1H-pyrazol-1-yl)-N-(3,4,4-trifluorobut-3-en-1- yl)acetamide 3,4,4-trifluorobut-3-en-1-yl 2-(5-(trifluoromethyl)-2H-tetrazol-2-yl)acetate; 3,4,4- trifluorobut-3-en-1-yl 2-(4,5-dichloro-1H-imidazol-1-yl)acetate; 4,4-difluorobut-3-en-1-yl 2-(3,5- dimethyl-1H-1,2,4-triazol-1-yl)acetate; 4,4-difluorobut-3-en-1-yl 2-(3,5-dimethyl-1H-pyrazol-1- yl)propanoate; 4,4-difluorobut-3-en-1-yl 2-(3,5-dimethyl-1H-pyrazol-1-yl)-2-methylpropanoate; 2-(4- chloro-1H-pyrazol-1-yl)-N-(4,4-difluorobut-3-en-1-yl)acetamide 3,4,4-trifluorobut-3-en-1-yl 2-(1H- benzo[d]imidazol-1-yl)acetate; 3,4,4-trifluorobut-3-en-1-yl 2-(1H-imidazol-1-yl)acetate; 4,4- difluorobut-3-en-1-yl 2-(1H-benzo[d]imidazol-1-yl)acetate; 4,4-difluorobut-3-en-1-yl 2-(1H- imidazol-1-yl)acetate; 3,4,4-trifluorobut-3-en-1-yl 2-(4-(trifluoromethyl)-1H-pyrazol-1-yl)acetate; 3,4,4-trifluorobut-3-en-1-yl 2-(4-chloro-3,5-dimethyl-1H-pyrazol-1-yl)-2-methylpropanoate; 3,4,4- trifluorobut-3-en-1-yl 2-(4-chloro-3,5-dimethyl-1H-pyrazol-1-yl)propanoate; 4,4-difluorobut-3-en-1- yl 2-(4-chloro-3,5-dimethyl-1H-pyrazol-1-yl)-2-methylpropanoate; 4,4-difluorobut-3-en-1-yl 2-(4- chloro-3,5-dimethyl-1H-pyrazol-1-yl)propanoate; 3,4,4-trifluorobut-3-en-1-yl 2-(3,5-dimethyl-1H- pyrazol-1-yl)propanoate; 4,4-difluorobut-3-en-1-yl 2-(2-methyl-1H-imidazol-1-yl)acetate; 4,4- difluorobut-3-en-1-yl 2-(5-methyl-2H-tetrazol-2-yl)acetate; 3,4,4-trifluorobut-3-en-1-yl 2-(5-methyl- 2H-tetrazol-2-yl)acetate; 4,4-difluorobut-3-en-1-yl 2-(4-(trifluoromethyl)-1H-pyrazol-1-yl)acetate; 4,4-difluorobut-3-en-1-yl 2-(2-cyclopropyl-1H-benzo[d]imidazol-1-yl)acetate; 3,4,4-trifluorobut-3- en-1-yl 2-(1H-benzo[d][1,2,3]triazol-1-yl)acetate; 4,4-difluorobut-3-en-1-yl 2-(1H- benzo[d][1,2,3]triazol-1-yl)acetate; 3,4,4-trifluorobut-3-en-1-yl 2-(5-methyl-1H-tetrazol-1-yl)acetate; 3,4,4-trifluorobut-3-en-1-yl 2-(3,5-bis(trifluoromethyl)-1H-pyrazol-1-yl)propanoate; 4,4-difluorobut- 3-en-1-yl 2-(3,5-bis(trifluoromethyl)-1H-pyrazol-1-yl)propanoate; 3,4,4-trifluorobut-3-en-1-yl 2-(3- chloro-1H-indazol-1-yl)acetate; 3,4,4-trifluorobut-3-en-1-yl 2-(3,5-dimethyl-1H-pyrazol-1-yl)-2- methylpropanoate; 3,4,4-trifluorobut-3-en-1-yl 2-(2-methyl-1H-imidazol-1-yl)acetate; 3,4,4- trifluorobut-3-en-1-yl 2-(4,5-dichloro-2-methyl-1H-imidazol-1-yl)acetate; 3,4,4-trifluorobut-3-en-1-yl 2-(3-chloro-1H-indazol-1-yl)-2-methylpropanoate; 3,4,4-trifluorobut-3-en-1-yl 2-(1H-pyrazol-1- yl)propanoate; 3,4,4-trifluorobut-3-en-1-yl 2-methyl-2-(1H-pyrazol-1-yl)propanoate; 3,4,4- trifluorobut-3-en-1-yl 2-(3-(trifluoromethyl)-1H-pyrazol-1-yl)propanoate; 3,4,4-trifluorobut-3-en-1-yl 2-methyl-2-(3-(trifluoromethyl)-1H-pyrazol-1-yl)propanoate; 3,4,4-trifluorobut-3-en-1-yl 2-(4- phenyl-1H-pyrazol-1-yl)acetate; 3,4,4-trifluorobut-3-en-1-yl 2-(4-chloro-3-methyl-5- (trifluoromethyl)-1H-pyrazol-1-yl)acetate; 3,4,4-trifluorobut-3-en-1-yl 2-(4-chloro-5-methyl-3- (trifluoromethyl)-1H-pyrazol-1-yl)acetate; 3,4,4-trifluorobut-3-en-1-yl 2-(4-(3,5-difluorophenyl)-1H- pyrazol-1-yl)acetate; 3,4,4-trifluorobut-3-en-1-yl 2-(2H-benzo[d][1,2,3]triazol-2-yl)propanoate; 3,4,4- trifluorobut-3-en-1-yl 2-(5-methyl-2H-tetrazol-2-yl)propanoate; 3,4,4-trifluorobut-3-en-1-yl 2-(1H- benzo[d][1,2,3]triazol-1-yl)propanoate; 3,4,4-trifluorobut-3-en-1-yl 2-(2-(trifluoromethyl)-1H- benzo[d]imidazol-1-yl)acetate; 3,4,4-trifluorobut-3-en-1-yl 2-(2-methyl-1H-benzo[d]imidazol-1- yl)acetate; 3,4,4-trifluorobut-3-en-1-yl 2-(2H-benzo[d][1,2,3]triazol-2-yl)-2-methylpropanoate; 3,4,4- trifluorobut-3-en-1-yl 2-(1H-benzo[d][1,2,3]triazol-1-yl)-2-methylpropanoate; 3,4,4-trifluorobut-3-en- 1-yl 2-methyl-2-(5-methyl-2H-tetrazol-2-yl)propanoate; 3,4,4-trifluorobut-3-en-1-yl 2-(4-chloro-1H- pyrazol-1-yl)butanoate; 3,4,4-trifluorobut-3-en-1-yl 2-(4-chloro-3,5-dimethyl-1H-pyrazol-1- yl)butanoate; 3,4,4-trifluorobut-3-en-1-yl 2-(3-(trifluoromethyl)-1H-pyrazol-1-yl)butanoate; 3,4,4- trifluorobut-3-en-1-yl 2-(5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl)butanoate; 3,4,4-trifluorobut- 3-en-1-yl 2-(3,5-bis(trifluoromethyl)-1H-pyrazol-1-yl)butanoate; 3,4,4-trifluorobut-3-en-1-yl 2-(3- methyl-1H-pyrazol-1-yl)butanoate; 3,4,4-trifluorobut-3-en-1-yl 2-(3-methyl-1H-indazol-1- yl)butanoate; 3,4,4-trifluorobut-3-en-1-yl 2-(4-chloro-1H-pyrazol-1-yl)-3-methylbutanoate; 3,4,4- trifluorobut-3-en-1-yl 2-(3,5-bis(trifluoromethyl)-1H-pyrazol-1-yl)-3-methylbutanoate; 3,4,4- trifluorobut-3-en-1-yl 3-methyl-2-(3-methyl-5-(trifluoromethyl)-1H-pyrazol-1-yl)butanoate; 3,4,4- trifluorobut-3-en-1-yl 3-methyl-2-(3-methyl-5-phenyl-1H-pyrazol-1-yl)butanoate; 3,4,4-trifluorobut- 3-en-1-yl 2-(4-chloro-3,5-dimethyl-1H-pyrazol-1-yl)-3-methylbutanoate; 3,4,4-trifluorobut-3-en-1-yl 2-(3,5-diphenyl-1H-pyrazol-1-yl)-3-methylbutanoate; 3,4,4-trifluorobut-3-en-1-yl 3-methyl-2-(3- methyl-1H-pyrazol-1-yl)butanoate; 3,4,4-trifluorobut-3-en-1-yl 3-methyl-2-(3-(trifluoromethyl)-1H- pyrazol-1-yl)butanoate and 3,4,4-trifluorobut-3-en-1-yl 3-methyl-2-(4-methyl-1H-pyrazol-1- yl)butanoate. 7. A process for preparing a compound of formula (I) and/or a salt thereof as claimed in claim 1, wherein said process comprises following steps (a) to (c): a) alkylating substituted compound of formula (2) with compound of formula 3 optionally in presence of suitable base and solvent to afford compound of formula (4) followed by hydrolysis of compound of formula (4) in presence of suitable acid/base and solvent to afford compound of formula (5) according to reaction scheme as depicted below:
Figure imgf000059_0001
b) converting sulfoxide compound of formula (5) to compound of formula (Ia) by alkylating the compound of formula (5) with compound of formula (6) to afford compound of formula (1a) according to reaction scheme as depicted below:
Figure imgf000060_0001
c) reacting substituted compound of formula (5) with amine compound of formula (6) to afford compound of formula (1b) optionally, followed by alkylating the compound of formula (1b) with compound of formula R-X to afford compound of formula (1c) according to reaction scheme as depicted below:
Figure imgf000060_0002
8. A composition for controlling or preventing phytopathogenic nematodes comprising a compound of general formula (I), stereoisomer, agriculturally acceptable salts, tautomers or N-oxides thereof as claimed in claim 1 and one or more inert carriers. 9. The composition as claimed in claim 7, wherein said composition may additionally comprises one or more active compatible compound selected from fungicides, insecticides, nematicides, acaricides, biopesticides, herbicides, plant growth regulators, antibiotics, nutrients or fertilizers. 10. The composition as claimed in claim 7 or 8, wherein the concentration of the compound of general formula (I) ranges from 1 to 90% 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. 11. A combination comprising the compound of general formula (I), stereoisomer, agriculturally acceptable salts, tautomers or N-oxides thereof as claimed in claim 1 and one or more active compatible compound selected from fungicides, insecticides, nematicides, acaricides, biopesticides, herbicides, plant growth regulators, antibiotics, nutrients and fertilizers. 12. Use of compound of general formula (I), stereoisomers, agriculturally acceptable salts, tautomers or N-oxides thereof or composition or combination thereof as claimed in claim 1 or 7 or 10, for controlling or preventing agricultural crops and/or horticultural crops against phytopathogenic fungi, bacteria, insects, nematodes, mites. 13. The use of compound of general formula (I) as claimed in claim 11, for controlling or preventing agricultural crops and/or horticultural crops against nematodes. 14. The use of the compounds of general formula (I) as claimed in claim 11 or 12, wherein said agricultural crops are selected from cereals, corn, rice, soybean and other leguminous plants, fruits and fruit trees, 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. 15. A seed comprising compound of formula (I) and/or stereoisomers or agriculturally acceptable salts or tautomers or N-oxides thereof or composition or combination thereof as claimed in claim 1 or 7 or 10, wherein the amount of the compound of the formula (I) or an N-oxide or an agriculturally acceptable salt thereof is ranging from 0.1 g to 10 kg per 100 kg of seed. 16. A method of controlling or preventing infestation of useful plants by phytopathogenic nematodes in agricultural crops and/or horticultural crops, wherein the compound of general formula (I) and/or stereoisomers or agriculturally acceptable salts or tautomers or N-oxides thereof or composition or combination thereof as claimed in claim 1 or 7 or 10, is applied to the plants, to parts thereof or a locus thereof. 17. A method of controlling or preventing infestation of useful plants by phytopathogenic nematodes in agricultural crops and/or horticultural crops, wherein the compound of general formula (I) and/or stereoisomers or agriculturally acceptable salts or tautomers or N-oxides thereof or composition or combination thereof as claimed in claim 1 or 7 or 10 is applied to the seeds of plants. 18. A method of controlling or preventing phytopathogenic nematodes in agricultural crops and or horticultural crops using the compound of general formula (I) and/or stereoisomers or agriculturally acceptable salts or tautomers or N-oxides thereof or composition or combination thereof as claimed in claim 1 or 7 or 10 comprising a step of applying an effective dosage of the compound or the composition or the combination, in amounts ranging from 1 g to 5 kg per hectare of agricultural and/or horticultural crops.
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