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WO2018116073A1 - Composés de 1,2,3-thiadiazole et leur utilisation en tant qu'agent de protection des cultures - Google Patents

Composés de 1,2,3-thiadiazole et leur utilisation en tant qu'agent de protection des cultures Download PDF

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Publication number
WO2018116073A1
WO2018116073A1 PCT/IB2017/057871 IB2017057871W WO2018116073A1 WO 2018116073 A1 WO2018116073 A1 WO 2018116073A1 IB 2017057871 W IB2017057871 W IB 2017057871W WO 2018116073 A1 WO2018116073 A1 WO 2018116073A1
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Prior art keywords
thiadiazole
difluoromethyl
phenyl
carboxamide
carbothioamide
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PCT/IB2017/057871
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English (en)
Inventor
G. Renugadevi
Siva Kumar Reddy KOTLA
M. Sathishkumar
Dipankar Roy
Mohan Lal MEHTA
Sulur G MANJUNATHA
Ramdas Balu GADAKH
Suresh Kumar SUTHAR
Ruchi GARG
Mohan S.P. KUMAR
Rupesh Kumar Mishra
Santosh Shridhar AUTKAR
Hagalavadi M VENKATESHA
Alexander G. M. KLAUSENER
Konstantin POSCHARNY
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PI Industries Ltd
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PI Industries Ltd
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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
    • C07D285/01—Five-membered rings
    • C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
    • C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
    • C07D285/06—1,2,3-Thiadiazoles; Hydrogenated 1,2,3-thiadiazoles
    • 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
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/82—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with three ring hetero atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
    • C07D217/12—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with radicals, substituted by hetero atoms, attached to carbon atoms of the nitrogen-containing ring

Definitions

  • the present invention relates to 1,2,3-thiadiazole compounds intended to protect crops by fighting against undesired phytopathogenic microorganisms. More precisely, the subject of the present invention relates to 1,2,3-thiadiazole carboxamide and thioamide compounds used to rotect crops by fighting against undesired phytopathogenic microorganisms.
  • W0199629871, WO2006098128 and WG2G10Q58830 discloses 1,2,3-thiadiazole carboxamide compounds and compositions containing these compounds for agricultural and horticultural crop disease control.
  • W0199854163 discloses a plant disease controlling agent containing 1,2,3- thiadiazole carboxamide compounds and a method for the use of these compounds.
  • JP 200G169461A discloses agricultural insecticidal and microbiocidal compounds composition comprising 1,2,3-thiadiazole carboxamide compounds.
  • JP2001139566 discloses pest control agent containing 1,2,3-thiadiazole carboxamide compounds and the method for using the same.
  • WO2000065914 discloses a fungicidal composition comprising 1 ,2,3-thiadiazole carboxamide compounds for seed treatment.
  • JP2001335570 discloses 1 ,2,3-thiadiazole carboxamide compounds for controlling insect pests, pathogenic fungi and weeds.
  • US 4,341,551 disclose 1,2,3 thiadiazole carboxylic acid derivatives as herbicide, fungicide and growth controlling agents.
  • WO2010037482 and WO2010089055 disclose use of sulfur-containing heterocyclic compounds for treating microbial and animal pathogens in plants of the family Musaceae.
  • CN106831647 disclosed 4-haioalkyl substituted 1,2,3 thiadiazole carboxamide derivative as insecticide.
  • a new family of compounds which possess the above mentioned effects or advantages.
  • a new family of compounds namely, 1, 2, 3-thiadiazole carboxamide or thioamide compounds wherein the substitution on thiadiazole and substitution on amine/aniline allow an unexpected and significantly higher activity against undesired microorganisms such as fungal or nematodes or bacterial pathogens.
  • This present invention relates to compounds of formula (I) and agronomically acceptable salts, metallic complexes, structural isomers, stereoisomers, diastereoisomers, enandomers, tautomers, or N- oxides thereof;
  • the present invention also relates to a composition
  • a composition comprising at least one compound of the present invention and at least one oilier active compound selected from fungicides, insecticides, nematicides, acaricides, biopesticides, herbicides, plant growth regulators, antibiotics, nutrients and or mixtures thereof.
  • the present invention further relates to the use of the compound, the combination or the composition of the present invention and method of using the same, particularly in the field of agriculture mainly for protecting plants.
  • the compounds of the present invention are novel and have enhanced activity against phytopathogens.
  • the compounds of the present invention have application in the field of agriculture or horticultural crops.
  • the present invention relates to compounds of formula (I) and agronomically acceptable salts, metallic complexes, structural isomers, stereo-isomers, diastereoisomers, enantiomers tautomers, or N-oxides thereof;
  • R represents hydrogen, halogen, cyano, nitro, N(R ⁇ )(R ' ), Ci-Ce-alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 - alkynyl, CrCe-haloaikyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -haloalkynyl, CrCe-alkoxy, CrC 6 - haloalkoxy, sulfanyl, pentafluoro-)>.
  • R 2 represents hydrogen, Ci-Ce-alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, Cj-C6-alkoxy or C 3 -C 6 - cycloalkyl which may be substituted by R 7 ; or
  • T represents G, S, N(R 5 ), N(OR 5 ) or N-N(R 5 )(R 6 );
  • R 5 and R 6 may be same or different and is independently selected from hydrogen, Ci-Ce-alkyl, Ci-Ce-halogenoalkyl, Ci-Ce-alkoxy, Cj -Ce-halogenoalkoxy, Ci-Ce-alkoxy-CrCe-alkyl, C 2 -C 6 - alkenyl, C 2 -C 6 -halogenoalkenyl, C 2 -C 6 -al.kynyl, C 2 -C 6 -halogenoalkynyl, C 3 -C 6 -cycloalkyl, C 3 - Ce-cycloalkyi-CrCfi-alkyl, C 3 -C 6 -halogenocycloalkyl, formyl, CrC 6 -alkylcarbonyl, CrC 6 - halogenoalkylcarbonyl, Ci-Ce-alkylsulphonyi, C C 6 -halogenoalkylsulphony
  • R 7 is selected from the group consisting of halogen, cyano, riitro, amino, Ci-Ce-alkyl, Cj -Ce- halogenoalkyl, Q-Ce-alkoxy, CrCe-halogenoaikoxy, Ci-Ce-alkyicarbonyi, CrC 6 - halogenoalkylcarbonyl, Ci-Cg-alkoxycarbonyl, Cj -Ce-halogenoalkoxycarbonyl, C ⁇ -C - alkylaniinocarbonyl, Ci-Ce-di-alkyiaminocarbonyl, carboxyl, Ci-Ce-alkylsulfanyl, pentafluoro- > profession 6 -surfanyi, non aromatic-C 3 -C 6 -carbocycle, non aromatic-C 3 -C 6 -heterocycle; R " is selected from the group consisting of hydrogen, halogen, nitro, cyano,
  • R 8a epresents pentafluoro- ⁇ 6 - sulfanyl or pentafluoro ⁇ 0 -sulfajnyl-d-C 3 -al.kyl;
  • R 9 and R 10 may be the same or different represents hydrogen, cyano, Ci-C 6 -alkyl, d-C 6 - halogenoalkyl, d-C 6 -alkoxy, d-C 6 -halogenoalkoxy, d-C 6 -alkylcarbonyl, d-C 6 - aikoxycarbony!, d-C 6 -halogenoa!koxycarbonyl, Ci-C 6 -alkylaminocarbonyl, d-C 6 -di- alkylaminocarbonyl, d-d-alkylsulfanyl, C 3 -C 6 -carbocycle, CVd-heterocycle; or
  • R 9 and R l together with the atom to which they are attached or together with further atoms selected from the group consisting of C, N, O, S and optionally including 1 to 3 ring members 2
  • R la from d-C 6 - alkyl halides
  • R a , R a and R 4a selected from hydrogen, halogens, cyano, Nitro, d-C6-halogenated alky], CrC 6 -alkoxy, amino sulfonyl halides, d-C 6 -sulfoxide base, d-d-sulfone, Ci-d-alkyl sulfonamide, phenyl, 1 -5 same or different R "" substituted phenyl containing from 1 -3 same or different and selected from the oxygen atoms, nitrogen or sulfur atoms a 5-or-6- membered heterocyclic ring, 1-4 same or different R " ' substituted containing from 1-3 same or different and selected from the oxygen atoms and nitrogen atoms or sulfur atoms of 5-or 6-membered ring, with the proviso that the R a , R 3a and R 4a there can be only one hydrogen; R 3a selected from halogens, nitro, nitrile, Ci-Ce-alky
  • substitution R 1 of compound of general formula (I) is selected from halogen, halogenoaJkyl selected from -CHC1 2 , -C(R b )F 2 , -CHF 2 , -C(R b ) 2 -CF 3 , -CHF-CF 3 , -CF 2 - CF 3 ,-CHF-CF 2 -CF 3 , -CH 2 F, haloalkoxyalkyl selected from -C(R b ) 2 OCF 3 , -C(R b ) 2 OCHF 2 , - C(R b ) 2 OCH 2 F, -Ci-Cg-halogenoalkylsulfanyl-Ci-Ci-aikyl seicted from -C(R b ) 2 SCF 3 , - CH(R b )SCF 3 , -C(Rb) 2 SCHF 2 , -CH(R b ) 2
  • R b represents, hydrogen, halogen, CrCe-alkyl, Ci-Ce-haioalkyl; and other substitutions as defined in one of above embodiment.
  • R 1 is selected from halogen, halogenoalkyl selected from -CHC1 2 , -C(R b )F 2 , -CHF 2 , - C(R b ) 2 -CF 3 , -CHF-CF 3 , -CF 2 -CF 3 ,-CHF-CF 2 -CF 3 , -CH 2 F, haloalkoxyalkyl selected from - C(R b ) 2 OCF 3 , -C(R b ) 2 OCHF 2 , -C(R b ) 2 OCH 2 F, -C 1 -C8-halogenoaIkyIsulfanyI-C 1 -C 2 -alkyl seicted from -C(R b ) 2 SCF 3 , -CH(R b )SCF 3 , -C(R b ) 2 SCHF 2 , -CH(R b )SCHF 2 , Ci
  • substitution T of compound of general formula (I) is S.
  • preferred compound of general formula (I) are:
  • 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 ail 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 ait.
  • 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.
  • 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.
  • 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 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.
  • transitional phrase “consisting essentially of” is used to define a composition or method that includes materials, steps, features, components or elements, in addition to those literally disclosed, provided that these additional materials, steps, features, components or elements do not materially affect the basic and novel characteristic(s) of the claimed invention.
  • the term “invertebrate pest” includes arthropods, gastropods and nematodes of economic importance as pests.
  • arthropod includes insects, mites, spiders, scorpions, centipedes, millipedes, pill bugs and symphylans.
  • gastropod includes snails, slugs and other Stylommatophora.
  • nematode refers to a living organism of the Phylum Nematoda.
  • helminths includes roundworms, heartworms, phytophagous nematodes (Nematoda), flukes (Tematoda), acanthocephala and tapeworms (Cestoda).
  • invertebrate pest control means inhibition of invertebrate pest development (including mortality, feeding reduction, and/or mating disruption), and related expressions are defined analogously.
  • agronomic or “agriculturally” 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).
  • 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.
  • horticultural crops e.g., greenhouse, nursery or ornamental plants not grown in a field
  • turf e.g., sod farm, pasture, golf course, lawn, sports field, etc.
  • wood products e.g., stored product, agro-forestry and vegetation management
  • public health i.e. human
  • animal health e.g., domesticated animals such as pets, livestock and poultry, undomesticated animals such as wildlife
  • Nonagronomic applications include protecting an animal from an invertebrate parasitic pest by administering a parasiticidally effeciive (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.
  • a parasiticidally effeciive i.e. biologically effective
  • 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.
  • 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. The meaning of various terms used in the description shall now be illustrated.
  • alkyl used either alone or in compound words such as “alkylthio” or “haloalkyl” or - N(alkyl) or alkyicarbonyialkyl or alkylsuphonylamino includes straight -chain or branched Q to C 2 4 alkyl, preferably Cj to C 15 alkyl, more preferably C ⁇ to C 10 alkyl, most preferably Cj to C 6 alkyl.
  • alkyl include methyl, ethyl, propyl, 1-methyiethyl, butyl, 1 - methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, pentyl, 1-methylbutyl, 2-methylbutyl, 3- methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, hexyl, 1,1-dimethylpropyi, 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 -e
  • the alkyl is at the end of a composite substituent, as, for example, in alkylcycloalkyl
  • the part of the composite substituent at the start for example the cycloalkyl
  • other radicals for example alkenyl, alkynyl, hydroxyl, halogen, carbonyl, carbonyloxy and the like, are at the end.
  • Alkenyl used either alone or in compound words includes straight-chain or branched Ci to C24 alkenes, preferably C ⁇ to C15 alkenes, more preferably C-, to C 10 alkenes, most preferably Ci to C 6 alkenes.
  • alkenes include ethenyl, 1 -propenyl, 2- propenyl, 1-methylethenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1 -methyl- 1 -propenyl, 2-methyl-l- propenyl, l-methyl-2 -propenyl, 2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4- pentenyl, 1 -methyl- 1-butenyl, 2-metliyl- 1-butenyl, 3 -methyl- 1-butenyl, l-methyl-2-butenyl, 2- methyl-2-butenyl, 3-methyl-2-butenyl, l-methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl-3- butenyl, l,l-dimethyl-2-propenyl, 1,2-dimethyl-l -propenyl, l,2-dimethyl-2-propen
  • 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 haloalkenvl and the like, unless defined specifically elsewhere.
  • alkynes include ethynyl, 1 -propynyl, 2-propynyl, 1-butynyl, 2- butynyl, 3-butynyl, l-methyl-2 -propynyl, 1-pentynyl, 2-pentynyi, 3-pentynyl, 4-pentynyl, 1- methyl-2-butynyl, l-methyl-3-butynyl, 2-methyl-3-butynyl, 3-methyl-l-butynyl, 1 , l-dimethyi-2- propynyl, 1 -ethyl -2-propynyl, 1-hexynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl, 1- methyl-2-pentynyl, l-methyl-3-pentynyl, l-methyl-4-pentynyl, 2
  • alkynyl can also include moieties comprised of multiple triple bonds such as 2,5-hexadiynyl. Cycloalkyl means alkyl closed to form a ring.
  • Representative examples include but are not limited to cyclopropyl, cyclopeiityi 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. Representative examples include but are not limited to cyclopropenyl, cyclopentenyl and cyclohexenyl. This definition also applies to cycloalkenyl as a part of a composite substituent, for example cycloalkenyialkyl etc., unless specifically defined elsewhere.
  • Cycloalkynyl means alkynyl closed to form a ring including monocyclic, partially unsaturated groups. Representative examples include but are not limited to cyclopropynyl, cyclopentynyl and cyclohexynyl. This definition also applies to cycloalkynyl as a part of a composite substituent, for example cycloalkynylalkyl etc., unless specifically defined elsewhere.
  • Cycloalkoxy, cycloalkenyloxy and the like are defined analogously.
  • Non limiting examples of cycloalkoxy include cyclopropyioxy, 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.
  • halogen either alone or in compound words such as “haioalkyl” or “halogenoalkyl”, includes fluorine, chlorine, bromine or iodine. Further, when used in compound words such as “haioalkyl” or “halogenoalkyl”, said alkyl may be partially or fully substituted with halogen atoms which may be the same or different.
  • haioalkyl examples include chloromethyl, bromomethyl, dichloromethyl, trichloromethyi, fluoromethyl, difluoromethyl, trifluoromethyi, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1-chloroethyl, 1-bromoethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-irifluoroethyl, 2-chloro-2-fluoroethyl, 2- chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl, pentafluoroethyl, 1,1- dichl.oro-2,2,2-trifluoroethyl, and l,l ,l-trifluoroprop-2-yl. This definition also applies to hai
  • haloalkenyl or “halogenoalkenyl”, “haloalkynyl” or “halogenoalkynyl” are defined analogously except that, instead of alkyl groups, alkenyl and alkynyl groups are present as a part of the substituent.
  • haloalkoxy or "halogenoalkoy” 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-trifluoroetlioxy, 2- chloro-2-fluoroethoxy, 2-chloro-2,2-difluoroethoxy, 2,2-dichloro-2-fluoroethoxy, 2,2,2- trichloroethoxy,
  • haloalkylthio or "haloalkylsufanyl” or “halogenoalkylsulfanyl” 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-difiuoroethyithio, 2,2,2-tri.fluoroethylthio, 2-chloro-2- fluoroethylthio, 2- chloro-2,2-difluoroethylthio, 2,2-dichloro-2-fluoroethylthio, 2,2,2 -trichloroet ylthio, pentafluoroethylthio and l
  • haloalkylsulfinyl examples include CF 3 S(G), CC1 3 S(G), CF 3 CH 2 S(G) and CF 3 CF 2 S(0).
  • haloalkylsulfonyl examples include CF 3 S(0) 2 , CC1 3 S(0) 2 , CF 3 CH 2 S(0) 2 and CF 3 CF 2 S(0) 2 .
  • Hydroxy means -OH
  • Amino means -N(R) 2 , wherein R can be H or any possible substituent such as alkyl
  • Carbonyl means -C(O)-
  • carbonyl oxy means -QC(Q) ⁇
  • sulfinyl means SO
  • sulfonyl means S(0) 2 .
  • alkoxy used either alone or in compound words included Cj to C 2 4 alkoxy, preferably Ci to Qs alkoxy, more preferably Ci to C 10 alkoxy, most preferably C. to C alkoxy.
  • 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, L l-dimethylbutoxy, 1,2-dimethylbutoxy, 1,3-dimethylbutoxy, 2,2- dimethylbutoxy, 2,3-dimethylbutoxy, 3,3-dimethylbutoxy, 1 -et ylbutoxy,
  • Alkoxyalkyl denotes alkoxy substitution on alkyl.
  • alkoxyalkyl examples include CH3OCH2, CH3OCH 2 CH 2 , CH3CH 2 OCH 2 , CH3CH 2 CH 2 CH 2 OCH 2 and CH 3 CH 2 OCH 2 CH 2 . This definition also applies to alkoxyaikyi as a part of a composite substituent, for example haloalkoxyalkyl, unless specifically defined elsewhere.
  • alkoxyalkoxy denotes alkoxy substitution on alkoxy.
  • alkylthio includes branched or straight-chain alkylthio moieties such as methylthio, ethylthio, propylthio, 1 -methylethylthio, butylthio, 1-methylpropyithio, 2-methylpropylthio, 1, 1 - dimethyiethylthio, pentylthio, 1 -methylbutylthio, 2-methylbutylthio, 3-methylbutylthio, 2,2- dimethylpropylthio, 1-ethylpropylthio, hexyithio, 1 , 1-diniethyl.propylthio, 1 ,2- dimethylpropylthio, 1 -methylpentylthio, 2-methylpentylthio, 3-methylpentylthio, 4- methylpentylthio, 1 , 1 -dimethylbutylthio, 1 ,2-dimemylbutylthio, 1
  • Halogenocycloalkyi halogenocycloalkenyi, alkylcycloalkyl, cycloaikylalkyl, cycioalkoxyalkyl, alkylsuifinylalkyl, alkylsulfonylalkyl, halogenoalkylcarbonyl, cycloalkylcarbonyl, halogenoalkoxylalkyl, and the like, are defined analogously to the above examples.
  • alkyithioalkyl denotes alkylthio substitution on alky] .
  • Representative examples of “alkylthioalkyl” or “alkylsulfanylalkyl” include -CH 2 SCH 2 , -CH 2 SCH 2 CH 2 , CH 3 CH 2 SCH 2 , CH 3 CH 2 CH 2 CH 2 SCH 2 and CH 3 CH 2 SCH 2 CH 2 .
  • Alkylthioalkoxy denotes alkylthio substitution on alkoxy.
  • cycloalkylalkylamino denotes cycloalkyi substitution on aikyl amino. This definition also applies to alkoxy as a part of a composite substituent, for example haloalkoxy, alkenylaikoxy, alkynylalkoxy, etc., unless specifically defined elsewhere.
  • alkoxyalkoxyalkyl alkyiaminoalkyl, dialkylaminoalkyl, cycloalkylaminoalkyl, cycloalkylaminocarbonyi and the like, are defined analogously to "alkylthioalkyl” or cycloalkylalkylamino .
  • Al koxy carbonyl is an alkoxy group bonded to a skeleton via a carbonyl group (-CO- ). This definition also applies to alkoxycarbonyi as a part of a composite substituent, for example cycloalkylalkoxycarbonyl and the like, unless specifically defined elsewhere.
  • alkoxycarbonylalkylamino denotes alkoxy carbonyl substitution on alkyi amino.
  • Alkylcarbonylalkylamino denotes alkyi carbonyl substitution on alkyi amino.
  • alkylthioaikoxycarbonyl, cycloalkylalkylaminoalkyl and the like are defined analogously.
  • alkylsulfinyl include but are not limited to methylsulphinyl, ethylsulphinyl, propyisulphinyl, 1 -methylethylsulphinyL butyl sulphinyl, 1-methylpropylsulphinyl, 2- met ylpropylsulphinyl, 1 , 1 -dimethylethylsulphinyl, pentyl sulphinyl, 1 -methylbutylsulphinyl, 2- methylbutylsulphinyl, 3-methylbutylsuiphinyi, 2,2-dimethylpropyisulphinyl, 1- ethylpropylsulphinyl, hexylsuiphinyi, 1, 1-dimethylpropylsulphinyl, 1,2-dimethylpropylsulphinyl, 1-methylpentylsulphinyl, 2-methylpentylsulphinyl, 3-methyl
  • arylsulfmyl includes Ar- S(O), wherein Ar can be any carbocyle or heterocylcie. This definition also applies to alkylsulphinyl as a part of a composite substituent, for example haloaikyisulphiny! etc., unless specifically defined elsewhere.
  • alkylsulfonyl examples include but are not limited to methylsulphonyi, ethylsulphonyl, propyl sulphonyl, 1-methylethylsulphonyl, butylsulphonyl, 1 -methylpropylsulphonyl, 2- methylpropylsulphonyl, 1,1 -dimethylethylsulphonyl, pentylsulphonyl, l-methylbutyl sulphonyl,
  • arylsulfonyl includes Ar-S(0) 2 , wherein Ar can be any carbocyle or heterocylcie. This definition also applies to alkylsuiphonyl as a part of a composite substituent, for example alkylsulphonylalkyl etc., unless defined elsewhere.
  • Carbocycle includes "aromatic carbocyclic ring system” and “nonaromatic carbocylic ring system” or polycyclic or bicyeiic (spiro, fused, bridged, nonfused) ring compounds in which 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 statisfied).
  • 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.
  • Heteroaryl means 5 or 6-membered, fully unsaturated monocyclic ring system containing one to four heteroatoms from the group of oxygen, nitrogen and sulphur; if the ring contains more than one oxygen atom, they are not directly adjacent; 5-membered heteroaryl 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) 2-furyl, 3-furyl, 2-thienyl, 3-thienyl, 2-pyrrolyl, 3-pyrrolyl, 3-isoxazolyl, 4-isoxazoiyl, 5-isoxazoiyl, 3-isothiazolyi, 4-isofhiazoiyl, 5-isothiazolyl, 3-pyrazolyl, 4-pyrazolyl
  • 6-membered heteroaryl which contains one to four nitrogen atoms: 6-membered heteroaryl groups which, in addition to carbon atoms, may contain, respectively, one to three and one to four nitrogen atoms as ring members, for example (but not limited thereto) 2-pyridinyl, 3- pyridinyL 4-pyridinyl, 3-pyridazinyl, 4-pyridazinyl, 2-pyrimidinyL 4-pyrimidinyl, 5-pyrimidinyL 2-pyrazinyl, l,3,5-triazin-2-yl, l,2,4-triazin-3-yl and 1,2,4, 5-tetrazin-3-yl; benzofused 5-membered heteroaryl containing one to three nitrogen atoms or one nitrogen atom and one oxygen or sulphur atom: for example (but not limited to) indol-l-yi, indol-2-yl, indol-3-yl, indol-4-yl, ind
  • lieterocycle means three- to fifteen-membered, preferably three- to tweleve-membered, saturated or unsaturated 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, aziridinyl,
  • Trialkylsilyl includes 3 branched and/or straight-chain alkyl radicals attached to and linked through a silicon atom such as trimethylsilyl, triethylsilyl and t-butyl-dimeihylsilyl.
  • alotriaikyisilyl denotes at least one of the three alkyl radicals is partially or fully substituted with halogen atoms which may be the same or different
  • Alkoxytrialkylsilyl denotes at least one of the three alkyl radicals is substituted with one or more alkoxy radicals which may be the same or different
  • Trialkylsilyloxy denotes a trialkylsilyl moiety attached through oxygen.
  • alkylcarbonyl examples include C(0)CH 3 , C(0)CH 2 CH 2 Ce 3 and C(0)CH(CH 3 ) 2 .
  • the terni haloalkylsufonylaminocarbonyl, alkylsulfonylaminocarbonyl, alkylthioaikoxycarbonyl, alkoxycarbonyi alkyl amino and the like are defined analogously
  • Ci-C 3 alkylsulfonyl designates methyl sulfonyl through propylsulfonyl
  • C 2 alkoxyalkyl designates CH 3 OCH 2
  • C 3 alkoxyalkyl designates, for example, CH 3 CH(OCH 3 ), CH 3 OCH 2 CH 2 or CH 3 CH 2 OCH 2
  • C 4 alkoxyalkyl designates the various isomers of an alkyl group substituted with an alkoxy group containing a total of four carbon atoms, examples including CH 3 CH 2 CH 2 OCH 2 and CH 3 CH 2 OCH 2 CH 2 .
  • the present invention also relates to a method for controlling unwanted microorganisms, wherein compounds of the formula (I) are applied to the microorganisms and/or in their habitat.
  • the present invention further provides a method for protecting seeds against unwanted microorganisms by using seed treated with at least one compound of the formula (I).
  • the compounds of the formula (I) can possess potent microbiocidal activity and can be used for the control of unwanted microorganisms, such as fungi, nematodes and bacteria, in crop protection and in the protection of such materials.
  • the compounds of the formula (I) can possess very good fungicidal properties and can be used in crop protection, for example for control of Plasmodiophoromycetes, Oomycetes, Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes and Deuteromycetes .
  • the compounds of the formula (I) can be used as nematicides in crop protection, for example, for control of Rhabditida, Dorylaimida, and Tryplonchida.
  • the compounds of the formula (I) can be used as bactericides in crop protection, for example, for control of Pseudomonadaceae, Rhizobiaceae, Enterobacteriaceae, Corynebacteriaceae and Streptomycetaceae.
  • the compounds of the formula (I) can be used as herbicides and can be effective against a broad spectrum of economically important mono- and dicotyledonous harmful plants.
  • Monocotyledonous broad-leaved weed species may include Avena, Lolium, Alopecurus, Phalaris, Echinochloa, Digitaria, Setaria and Cyperus species from the annual group and perennial species Agropyron, Cynodon, Imperata and Sorghum and also perennial Cyperus species.
  • Dicotyledonous broad-leaved weed species may include Galium, Viola, Veronica, Lamium, Stellaria, Amaranthus, Sinapis, Ipomoea, Sida, Matricaria and Abutilon on the annual side, and also Convolvulus, Cirsium, Rumex and Artemisia in the case of the perennial broad- leaved weeds. Harmful plants that occur in rice, such as, for example, Echinochloa, Sagittaria,
  • Alisma, Eieocharis, Scirpus and Cypems, can be controlled by the compounds of formula (I).
  • the compounds of the formula (I) can be used for curative or protective control of phytopathogenic fungi.
  • the invention therefore also relates to curative and protective methods for controlling phytopathogenic fungi by the use of the inventive active ingredients or compositions, which are applied to the seed, the plant or plant parts, the fruit or the soil in which the plants grow.
  • the compounds of the formula (I) can be used for controlling or preventing against phytopathogenic fungi, bacteria, insects, nematodes, mi es of agricultural crops and or horticultural crop s .
  • 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 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.
  • a carrier is a natural or synthetic, organic or inorganic substance with which the active ingredients are mixed or combined for better applicability, in particular for application to plants or plant parts or seed.
  • the carrier which may be solid or liquid, are generally inert and should be suitable for use in agriculture.
  • Useful solid carriers include for example ammonium salts and natural rock flours, such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, and synthetic rock flours, such as finely divided silica, alumina and silicates; useful solid carriers for granules include: for example, crashed and fractionated natural rocks such as calcite, marble, pumice, sepiolite and dolomite, and also synthetic granules of inorganic and organic flours, and granules of organic material such as paper, sawdust, coconut shells, maize cobs and tobacco stalks; useful emulsifiers and/or foam-formers include: for example nonionic and anionic emulsifiers, such as polyoxyethvlene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example alkylaryi polyglycol ethers, alkylsulphonates, alkyl sulphates,
  • POE- and/or POP-polyol derivatives POE- and/or POP-sorbitan or -sugar adducts, alkyl or aryl sulphates, alkyl- or arylsulphonates and alkyl or aryl phosphates or the corresponding PO-ether adducts.
  • suitable are oligo- or polymers, for example those derived from vinylic monomers, from acrylic acid, from EO and/or PO alone or in combination with, for example, (poly) alcohols or (poly) amines. It is also possible to use lignin and its sulphonic acid derivatives, unmodified and modified celluloses, aromatic and/or aliphatic sulphonic acids and also their adducts with formaldehyde.
  • the active ingredients can be applied as such or converted to the customary formulations or in the form of their formulations or the use forms prepared therefrom, such as ready-to-use solutions, emulsions, water- or oil-based suspensions, powders, wettabie powders, pastes, soluble powders, soluble tablets, dusts, soluble granules, granules for broadcasting, suspoemulsion concentrates, natural products impregnated with active ingredient, synthetic substances impregnated with active ingredient, nutrients and also microencapsulations in polymeric substances.
  • Application is accomplished in a customary manner, for example by watering, spraying, atomizing, nursery boxes, broadcasting, dusting, foaming, spreading-on and the like. It is also possible to deploy the active ingredients by the ultra-low volume method or to inject the active ingredient preparation or the active ingredient itself into the soil. It is also possible to treat the seeds of the plants.
  • the active ingredients can be further converted to the nanoformulation with intent to further improve water solubility, thermal stability, bioavailability, sensory attributes, and physiological performance.
  • the formulations mentioned can be prepared in a manner known per se, for example by mixing the active ingredients with at least one customary extender, solvent or diluent, emulsifier, dispersant and/or binder or fixing agent, wetting agent, a water repellent, if appropriate siccatives and UV stabilizers and if appropriate dyes and pigments, antifoams, preservatives, secondary- thickeners, stickers, gibberellins and also other processing auxiliaries.
  • the present invention includes not only formulations which are already ready for use and can be deployed with a suitable apparatus to the plant or the seed, but also commercial concentrates which have to be diluted with water prior to use.
  • auxiliaries used may be those substances which are suitable for imparting particular properties to the composition itself and/or to preparations derived therefrom (for example spray liquors, seed dressings), such as certain technical properties and/or also particular biological properties.
  • Typical auxiliaries include extenders, solvents and carriers.
  • Suitable extenders are, for example, water, polar and nonpolar organic chemical liquids, for example from the classes of the aromatic and nonaromatic hydrocarbons (such as paraffins, alkylbenzenes, alkylnaphthalenes, chlorobenzenes), the alcohols and polyols (which may optionally also be substituted, etherified and/or esterified), the ketones (such as acetone, cyclohexanone), esters (including fats and oils) and (poly) ethers, the unsubstituted and substituted amines, amides, lactams (such as N-alkylpyrrolidones) and lactones, the sulphones and sulphoxides (such as dimethyl sulphoxide).
  • Liquefied gaseous extenders or carriers are understood to mean liquids which are gaseous at standard temperature and under standard pressure, for example aerosol propellants such as halohydrocarbons, or else butane,
  • tackifiers such as carboxymethylcellulose, natural and synthetic polymers in the form of powders, granules or latices, such as gum arabic, polyvinyl alcohol and polyvinyl acetate, or else natural phospholipids such as cephalins and lecithins and synthetic phospholipids.
  • Further additives may be mineral, vegetable oils and methylated seed oils.
  • Useful liquid solvents are essentially: aromatics such as xylene, toluene or alkylnaphthalenes, chlorinated aromatics or chlorinated aliphatic hydrocarbons such as chlorobenzenes, chloroethylenes or methylene chloride, aliphatic hydrocarbons such as cyclohexane or paraffins, for example petroleum fractions, alcohols such as butanol or glycol and their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents such as dimethylformamide and dimethyl sulphoxide, or else water.
  • aromatics such as xylene, toluene or alkylnaphthalenes
  • chlorinated aromatics or chlorinated aliphatic hydrocarbons such as chlorobenzenes, chloroethylenes or methylene chloride
  • aliphatic hydrocarbons such as
  • compositions comprising compounds of the formula (I) may additionally comprise further components, for example surfactants.
  • surfactants are emulsifiers and/or foam formers, dispersants or wetting agents having ionic or nonionic properties, or mixtures of these surfactants.
  • Examples thereof are salts of polyacrylic acid, salts of lignosulphonic acid, salts of phenolsulphonic acid or naphthalenesulphonic acid, polycondensates of ethylene oxide with fatty alcohols or with fatty acids or with fatty amines, substituted phenols (preferably alkylphenols or arylphenols), salts of sulphosuccinic esters, taurine derivatives (preferably alkyl taurates), phosphoric esters of polyethoxylated alcohols or phenols, fatty esters of polyois, and derivatives of the compounds containing sulphates, sulphonates and phosphates, for example alkylaryl poiyglycoi ethers, alkylsulphonates, alkyl sulphates, arylsulphonates, protein hydrolysaies, lignosulphite waste liquors and methylcellulose.
  • the presence of a surfactant is necessary if one of the active ingredients and/or one of the
  • dyes such as inorganic pigments, for example iron oxide, titanium oxide and Prussian Blue, and organic dyes such as alizarin dyes, azo dyes and metal phthalocyanine dyes, and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.
  • Further additives may be perfumes, mineral or vegetable, optionally modified oils, waxes and nutrients (including trace nutrients), such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.
  • Additional components may be stabilizers, such as cold stabilizers, presen'atives, antioxidants, light stabilizers, or other agents which improve chemical and/or physical stability.
  • additional components may also be present, for example protective colloids, binders, adhesives, thickeners, thixotropic substances, penetrants, stabilizers, sequestering agents, complex formers.
  • the active ingredients can be combined with any solid or liquid additive commonly used for formulation purposes.
  • the formulations contain generally between 0.05 and 99% by weight, 0.01 and 98% by weight, preferably between 0.1 and 95% by weight, more preferably between 0.5 and 90% of active ingredient, most preferably between 10 and 70% by weight.
  • the formulations described above can be used for controlling unwanted microorganisms, in which the compositions comprising compounds of the formula (I) are applied to the microorganisms and/or in their habitat.
  • 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 compounds selected from fungicides, bactericides, acaricides, insecticides, nemadcides, herbicides, biopesticides, plant growth regulators, antibiotics, nutrients and/or mixtures thereof.
  • the present invention further relates to a composition wherein the concentration of compounds having 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 agrochemicai compositions generally comprise between 0.01 and 95%, preferably between 0.1 and 90%, more preferably between 1 and 70%, and in particular between 10 and 60%, by weight of active substance.
  • the active substances are employed in a purity of from 90% to 100%, preferably from 95% to 100% (according to NMR spectrum).
  • solutions for seed treatment (IS), Suspoemulsions (SE), flowable concentrates (FS), powders for dry treatment (OS), water- dispersible powders for slurry treatment (WS), water- soluble powders (SS), emulsions (ES), emulsifiable concentrates (EC), and gels (GF) are usually employed.
  • compositions in question give, after two-to-tenfold dilution, active substance concentrations of from 0.01 to 60% by weight, preferably from 0.1 to 40%, in the ready-touse preparations.
  • Application can be carried out before or during sowing.
  • Methods for applying compound I and compositions thereof, respectively, onto plant propagation material, especially seeds include dressing, coating, pelleting, dusting, and soaking as well as in-furrow application methods.
  • compound I or the compositions thereof, respectively are applied on to the plant propagation material by a method such that germination is not induced, e. g. by seed dressing, pelleting, coating and dusting.
  • the amounts of active substances applied are, depending on the kind of effect desired, from 0.001 to 2 kg per ha, preferably from 0.005 to 2kg per ha, more preferably from 0.05 to 0.9 kg per ha, and in particular from 0.1 to 0.75 kg per ha.
  • amounts of active substance of from 0.1 to 1000 g, preferably from 1 to 40 1000 g, more preferably from 1 to 100 g and most preferably from 5 to 100 g, per 100 kilogram of plant propagation material (preferably seeds) are generally required.
  • the amount of active substance applied depends on the kind of application area and on the desired effect.
  • Amounts WO 2017/081312 PCT/EP2016/077524 customarily applied in the protection of materials are 0.001 g to 2 kg, preferably 0.005 g to 1kg, of active substance per cubic meter of treated material.
  • Compounds of the formula (I) according to this invention, as well as salts, N-oxides, metal complexes, stereoisomers or polymorphs can be used as such or in formulations thereof and can be mixed with known mixing partners in order to broaden, for example, the activity spectrum or to prevent development of resistance.
  • Useful mixing partners include, for example, known fungicides, insecticides, acaiicides, nematicides, biopesticides and bactericides.
  • Ail named mixing partners of the classes (A) to (O) as described below can, if their functional groups enable this, optionally form salts with suitable bases or acids, appear as stereoisomers, even if not specifically mentioned in each case, or as polymorphs. They are also understood as being included herein.
  • A) Inhibitors of the ergo sterol biosynthesis for example (A01) aldimorph, (A02) azaconazole, (A03) bitertanol, (A04) bromuconazole, (AOS) cyproconazole, (A06) diclobutrazole, (A07) difenoconazole, (AOS) diniconazole, (A09) diniconazole-M, (A 10) dodemorph, (Al l) dodemorph acetate, (A12) epoxiconazole, (A13) etaconazole, (A14) fenarimol, (A 15) fenbuconazole, (A16) fenhexamid, (A17) fenpropidin, (A18) fenpropimorph, (A19) fluquinconazole, (A20) flurprimidol, (A21) flusilazole, (A01) al
  • B) Inhibitors of the respiratory chain at complex I or II for example (B01) bixafen, (B02) boscalid, (B03) carboxin, (B04) cypropamide, (BOS) diflumetorim, (B06) fenfuram, (B07) fluopyram, (B08) flutolanil, (B09) fluxapvroxad, (B IO) furametpyr, (B l l) turmecyclox, (B 12) isopyrazam (mixture of syn-epimeric racemate 1RS,4SR,9RS and anti-epimeric racemate 1RS,4SR,9SR), (B13) isopyrazam (anti-epimeric racemate 1RS,4SR,9SR), (B 14) isopyrazam (anti-epimeric enantiomer 1R,4S,9S), (B15) isopyrazam (anti-epimeric enantiomer 1S
  • D) Inhibitors of the mitosis and cell division for example (DOT) benomyl, (D02) carbendazim, (D03) chlorfenazole, (D04) diethofencarb, (D05) ethaboxam, (D06) fluopicolide, (D07) fiiberidazole, (DOS) pencycuron, (D09) thiabendazole, (D1.0) thiophanate-methyl, (Dl l) thiophanate, (D12) zoxamide, (D13) 5-chloro-7-(4-methylpiperidin- l-yl)-6-(2,4,6- trifluorophenyl)[l,2,4]triazol.o l ,5-aJpyrimidine, (D14) 3-chloro-5-(6-chloropyridin-3-yl)-6- methyl-4-(2,4,6- trifluorophenyl) pyridazine.
  • F Compounds capable to induce a host defence, for example (F01) acibenzolar-S-methyl, (F02) isotianil, (F03) probenazole, (F04) tiadinil, (F05) laminarin.
  • G Inhibitors of the amino acid and/or protein biosynthesis, for example (G01) andoprim, (G02) blasticidin-S, (G03) cyprodinil, (G04) kasugamycin, (G05) kasugamycin hydrochloride hydrate, (G06) mepanipyrim, (G07) pyrimethanil, (G08) 3-(5-fluoro-3,3,4,4-tetramethyl-3,4- dihydroisoquinolin-l-yl)quinoline, (G09)oxytetracycline,(G10)streptomycin.
  • G01 andoprim
  • G02 blasticidin-S
  • G03 cyprodinil
  • G04 kasugamycin
  • G05 kasugamycin hydrochloride hydrate
  • G06 mepanipyrim
  • G07 pyrimethanil
  • G08 3-(5-fluoro-3,3,4,4-tetramethyl-3,4- dihydroisoquinol
  • H Inhibitors of the ATP production, for example (HOI) fentin acetate, (H02) fentin chloride, (H03) fentinhydroxide, (H04) silthiofam.
  • Inhibitors of the cell wall synthesis for example (101) benthiavalicarb, (102) dimethomorph, (103) flumorph, (104) iprovalicarb, (105) mandipropamid, (106) polyoxins, (107) polyoxorim, (108) vaiidamycin A, (109) valifenaiate, (110) polyoxin B, (11 1) (2E)-3-(4-tert- butylphenyl)-3-(2-chIoropyri.din-4-yl)-l -(morpholin-4-yI)prop-2-en-l-one, (112) (2Z)-3-(4-tert- butylphenyl)-3-(2-chloropyridii -4-yl)-l-(morpholin-4-yl)prop-2-en-l-one.
  • J) Inhibitors of the lipid and membrane synthesis for example (J01) biphenyl, (J02) chloroneb, (J03) dicloran, (.104) edifenphos, (J05) etridiazole, (J06) iodocarb, (.107) iprobenfos, (J08) isoprothiolane, (J09) propamocarb, (J 10) propamocarb hydrochloride, (Jl l) prothiocarb, (J12) pyrazophos, (J13) quintozene, (.114) tecnazene, (J 15) toclofos-methyl.
  • K) Inhibitors of the melanin biosynthesis for example (K01 ) carpropamid, (K02) diclocymet, (K03) fenoxanil, (K04) phthalide, (K05) pyroquilon, (K06) tolprocarb, (K07)tricyclazole.
  • L) Inhibitors of the nucleic acid synthesis for example (L01) benalaxyl, (L02) benalaxyl-M (kiralaxyl), (L03) bupirimate, (L04) clozylacon, (LOS) dimethirimol, (L06) ethirimol, (L07) furalaxyl, (L08) hymexazol, (L09) metalaxyl, (L10) metalaxyl-M (mefenoxam), (Ll l) ofurace, (L12) oxadixyl, (L13) oxoiinic acid, (L1.4)octhilinone.
  • Inhibitors of the nucleic acid synthesis for example (L01) benalaxyl, (L02) benalaxyl-M (kiralaxyl), (L03) bupirimate, (L04) clozylacon, (LOS)
  • M Inhibitors of the signal transduction, for example (M01 ) chlozolinate, (M02) fenpiclonil, (M03) fludioxonil, (M04) iprodione, (M05) procymidone, (M06) quinoxyfen, (M07) vinclozolin, (M08) proquinazid.
  • the compound of formula (I) can be mixed with one or more active compatible compound selected from insecticides/acaricides/neniaticides class, which are specified herein by their common names that are known and described, for example in The Pesticide Manual 17 th Ed., or can be searched in the internet (e.g. under www.alanwood.net/pesticides).
  • Acetylcholinesterase (AChE) inhibitors such as carbamates, for example alanycarb, aldicarb, bendiocarb, benfuracarb, butocarboxira, butoxycarboxim, carbaryl, carbofuran, carbosuifan, ethiofencarb, fenobucarb. forrnetanate, f rathiocarb, isoprocarb, metliiocarb.
  • AChE Acetylcholinesterase
  • GABA-gated chloride channel antagonists such as cyclodiene organodiioriiies, for example chlordaiie and endosulfan or pbenvlpvrazoles (fiproles), for example ethiproie and fiproni!.
  • Sodium channel modulators/voltage-dependent sodium channel blockers such as pyretfcroids, for example acrinathrin, allethrin, d-cis-trans allethrin, d- trans allethrin, bifenthrin, bioal!ethrin, bioallethrin S-cyclopentenyl isomer, bioresmethrin, cycloprothrin, cyfl.uih.rin, bela-cyfl.uih.rin, eyhalothrin, lambda-cyhalothrin, gamma-cyhalothrin, cypermethrin, alpha-cypem ethrin, beta- c yperi nethrin , theta-c y ermeihrin, zeia-cypermeihrin , eyphenofhrin [( 1R )-t
  • Nicotinic acetylcholine receptor (rs.ACbR) competitive modulators such as neonicotinoids, for example acetamiprid, elothiaiiidin, dinotefuran, imidacloprid, niteiipyram, thiacloprid and iliia.mer.liox am or nicotine or sulfoxaflor or Oupyradi urone.
  • neonicotinoids for example acetamiprid, elothiaiiidin, dinotefuran, imidacloprid, niteiipyram, thiacloprid and iliia.mer.liox am or nicotine or sulfoxaflor or Oupyradi urone.
  • Nicotinic acetylcholine receptor (nACliR) allosteric modulators such as spinosyns, for example spinetoram and spiiiosad.
  • Glutamate-gaied chloride channel (GluCl) allosteric modulators such as avennectins / milbemycins, for example abamectin, emamectin benzoate, lepimeciin and milbemectin,
  • Juvenile hormone mimics such as juvenile hormone analogues, for example hydroprene, kinoprene and meth prene or fenoxycarb or pyriproxyfen.
  • Active compounds with unknown or non-specific mechanisms of action such as alkyl halides for example as methyl bromide and other alkyl halides or chloropicrin or fluorides or borates or tartar emetic or methyl isocyanate generators.
  • Chordotonai organ TRPV channel modulators such as pyridine azomethine derivatives, for example pyme rozine and pyrifluquinazon or flonicamid,
  • Mite growth inhibitors for example clofentezine, hexylhiazox and diflovidazin or etoxazole.
  • Microbial disrupters of insect gut midgut for example Bacillus thuringiensis subspecies israelensis. Bacillus thuringiensis subspecies aizawai, Bacillus thuringiensis subspecies kurstaki. Bacillus thuringiensis subspecies tenehrionis and Bacillus sphaericus and BT crop proteins: CrylAb, CrvlAc, CrvlFa, CrylA 105, Cry2Ab, Vip3a, mCrySA, Cry3Ab, Cry3Bb, Cry34Abl / Cry35Abl.
  • Inhibitors of mitochondrial ATP synthase such as organodn miticides, for example azocyelotin, cyhexatin and fenbutatin oxide or diafentliiuron or propargite or tetradifon.
  • organodn miticides for example azocyelotin, cyhexatin and fenbutatin oxide or diafentliiuron or propargite or tetradifon.
  • Nicotinic acetylcholine receptor (iiAChR) channel blockers such as bensultap, eartap- hydrochloride, thiocyclam and thiosultap-sodium,
  • Inhibitors of chit i biosynthesis, type 0, such as bistrifluoron, chlorfluazuron. difhibenzuron, fliicycioxiiron, fiufenoxuron, hexaflumuron, !ufenuron, novahiron, novifiumuron, teflubenzuroii and triflumuroii.
  • Inhibitors of chitin biosynthesis type 1. such as buprofezin,
  • Molting disrupters (particularly in Dipteran), such as cyromazine
  • Ecclysone receptor agonists such as chromafenozide, halofenozide, methoxyfenozide and tebufenozide.
  • Octopamine receptor agonists such as amitraz.
  • Mitochondrial complex III electron transport inhibitors such as hydramethyinon or acequinocyl or fluacrypyrim or bifenazate.
  • (23) inhibitors of acetyl CoA carboxylase such as tetronic and tetramic acid derivatives, for example spirodiclofen, spiromesifen and spirotetramat.
  • Mitochondrial complex IV electron transport Inhibitors such as phosphides, for example aluminum phosphide, calcium phosphide, zinc phosphide and phosphlne or cyanides.
  • Mitochondrial complex II electron transport Inhibitors such as heta-ketonilrlle derivatives, for example cyeiiopyrafen and eyflumetofen or carboxanilides.
  • afidopyropen afoxolaner, azadirachtin, benclothiaz, benzoximate, bifenazate, broflanilide, bromopropylate, chinomethionat, cryolite, cycianillprole, eyeloxaprid, cyhalodiamide, dicloromezodaz, dieofol, dlflovidazin, flometoquin, fi uazaindolizine, lluensulibiie, flufeiierim, ilufenoxystrobin, flufiprole, fluhexafon, fluopyram, fluralaner, fluxametamide, fufenozide.
  • guadipyr heptafiuthrin, irnldac otliiz, iprodlone, lotilaner, meperfluthriii, paichongdiiig, pyflubumide, pyridaly , pyrifhiquinazon, pyriminostrobin, sarolaner, tetramethylftuthrin, tetraniliprole, tetrachlorantraniliprole, tioxazafeii, trifluraezopyrim and iodomethane; iiirthermore, preparations based on Bacillus firtnus (1-1582, BioNeem, Votivo), and the following known active compounds: l- ⁇ 2-fluoiO ⁇ 4 ⁇ meihyI-5-[(2,2,2 ⁇
  • the compounds of formula (I) may be used to treat several fungal pathogens.
  • pathogens of fungal diseases which can be treated in accordance with the invention include: diseases caused by powdery mildew pathogens, for example Blumeria species, for example
  • Podosphaera species for example Podosphaera leucotricha
  • Sphaerotheca species for example Sphaerotheca fuliginea
  • Uncinuia species for example Uncinuia necator
  • Erysiphe species for example Erysiphe dehor ac earn:
  • Gymnosporangium species for example Gymnosporangium sabinae
  • Hemileia species for example Hemileia vastatrix
  • Phakopsora species for example Phakopsora pachyrhizi or Phakopsora meihomiae
  • Puccinia species for example Puccinia recondita, Puccinia graminis oder Puccinia striiformis
  • Uromyces species for example Uromyces appendiculatus ;
  • Albugo species for example Albugo Candida
  • Bremia species for example Bremia lactucae
  • Peronospora species for example Peronospora pisi or P. brassicae
  • Phytophthora species for example Phytophthora infestans
  • Plasmopara species for example Plasmopara viticola
  • Pseudoperonospora species for example Pseudoperonospora humuli or Pseudoperonospora cubensis
  • Pythium species for example Pythium ultimum
  • Pythium species for example Pythium ultimum
  • leaf blotch diseases and leaf wilt diseases caused, for example, by Aiiernaria species, for example Alternaria solani; Cercospora species, for example Cercospora beticola; Cladiosporium species, for example Cladiosporium, cucumerinum,; Cochliobolus species, for example Cochliobolus sativus (conidial form: Drechslera, syn: Helminthosporium) or Cochliobolus miyabeanus; Colletoirichum species, for example Colletoirichum lindemuthanium; Cycloconium species, for example Cycloconium oleaginum; Diaporthe species, for example Diaporthe citri Elsinoe species, for example Elsinoe fawcettii; Gloeosporium species, for example Gloeosporium laeticolor; Glomerella species, for example Glomerella cingulata; Guignardia species, for example Guignard
  • Mycosphaerella species for example Mycosphaerella graminicola, Mycosphaerella arachidicola or Mycosphaerella fijiensis
  • Phaeosphaeria species for example Phaeosphaeria nodoruni
  • Pyrenophora species for example Pyrenophora teres or Pyrenophora tritici repenlis
  • Ramularia species for example Ramularia collo-cygni or Ramularia areola: Rhynchosporium species, for example Rhynchosporium secalis; Septoria species, for example Septoria apii or Septoria lycopersici; Stagonospora species, for example Stagonospora nodorum; Typhula species, for example Typhula incarnata; Venturia species, for example Venturia inaequalis;
  • Corticium species for example Corticium graminearum
  • Fusarium species for example Fusarium oxysporum
  • Gaeumannomyces species for example Gae niannomyces graminis
  • Plasmodiophora species for example Plasmodiophora brassicae
  • Rhizoctonia species for example Rhizoctonia solani
  • Sarocladium species for example Sarocladium oryzae
  • Sclerotium species for example Sclerotium oryzae
  • Tapesia species for example Tapesia acuformis
  • Thielaviopsis species for example Thielaviopsis basicola
  • Ganoderrna species for example Ganoderrna lucidum
  • Thielaviopsis species for example Thielaviopsis basicola
  • Ganoderrna species for example Ganoderrna lucidum
  • ear and panicle diseases caused, for example, by Alternaria species, for example Alternaria spp.; Aspergillus species, for example Aspergillus flavus; Cladosporium species, for example Cladosporium cladosporioides; Claviceps species, for example Claviceps purpurea; Fusarium species, for example Fusarium culmorum; Gibberella species, for example Gibberella zeae; Monographella species, for example Monographella nivalis; Stagnospora species, for example Stagnospora nodorum;
  • Sphacelotheca species for example Sphacelotheca reiliana
  • Tilletia species for example Tilletia caries or Tilletia controversa
  • Urocystis species for example Urocystis occulta
  • Ustilago species for example Uslilago nuda
  • Alternaria species for example Alternaria brassicicola
  • Aphanomyces species for example Aphanomyces euteiches
  • Ascochyta species for example Ascochyta lends
  • Aspergillus species for example Aspergillus flavus
  • Cladosporium species for example Cladosporium herbarum
  • Cochliobolus species for example Cochliobolus sativus (conidial form: Drechslera, Bipolaris Syn: Helminthosporium); Colletotrichurn species, for example Colletotrichum coccodes
  • Fusarium species for example Fusarium culmorum Gibberella species, for example Gibberella zeae
  • Macrophomina species for example Macrophomina phaseolina
  • Microdochiurn species for example Microdochiurn nivale: Monographella species,
  • Nectria species for example Nectria galligena:
  • wilt diseases caused, for example, by MonUinia species, for example Monilinia laxa;
  • Exobasidium species for example Exobasidium vexans
  • Taphrina species for example Taphrina deformans
  • degenerative diseases in woody plants caused, for example, by Esca species, for example Phaeomoniella chlamydospora, Phaeoacremonium aleophilum or Fomitiporia mediterranea; Ganoderma species, for example Ganoderma boninense;
  • Botrytis species for example Botrytis cinerea
  • Rhizoctonia species for example Rhizoctonia solani
  • Helminthosporium species for example Helminthosporium solani
  • diseases caused by bacterial pathogens for example Xanthomonas species, for example Xanthomonas carnpestris pv. oryzae; Pseudomonas species, for example Pseudomonas syringae /; ⁇ ! . lachrymans; Erwinia species, for example Erwinia amylovora Ralstonia species, for example Ralstonia solanacearum;
  • phytophthora rot (Phytophthora megasperma), brown stem rot (Phialophora gregatd), pythium rot (Pythium aphaniderrnaium, Pythiurn irregulare, Pythium deharyanum, Pythium myrioiyium, Pythium ultimuni), rhizoctonia root rot, stem decay, and damping-off (Rhizoctonia solani), sclerotinia stem decay (Sclerotinia sclerotiorum), sclerotinia southern blight (Sclerotinia roljsii), thielaviopsis root rot (Thielaviopsis basicola).
  • 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 Glohodera species; Heterodera avenae, Heterodera glycines, Heterodera schachtii, Heterodera trifolii, and other Heterodera species; Seed gall nematodes, Anguina species; Stem and foliar nematodes,
  • Plants which can be treated in accordance with the invention include the following: Rosaceae sp (for example pome fruits such as apples, pears, apricots, cherries, almonds and peaches), Rihesioidae sp.,
  • Juglandaceae sp. Betulaceae sp., Anacardiaceae sp., Fagaceae sp., Moraceae sp., Oleaceae sp.,
  • Actinidaceae sp. Lauraceae sp., Musaceae sp. (for example banana trees and plantations),
  • Rubiaceae sp. for example coffee
  • Theaceae sp., Sterculiceae sp., Rutaceae sp. for example lemons, oranges and grapefruit
  • Vitaceae sp. for example grapes
  • Solanaceae sp. for example tomatoes, peppers
  • Liliaceae sp. for example lettuce
  • Umbelliferae sp., Cr ciferae sp. Chenopodiaceae sp.
  • Cucurbitaceae sp. for example cucumber
  • Alliaceae sp. for example leek, onion
  • Papilionaceae sp. for example peas
  • major crop plants such as PoaceaeiGramineae sp. (for example maize, turf, cereals such as wheat, rye, rice, barley, oats, millet and triticale),
  • Asteraceae sp. for example sunflower
  • Brassicaceae sp. for example white cabbage, red cabbage, broccoli, cauliflower, Brussels sprouts, pak choi, kohlrabi, radishes, and oilseed rape, mustard, horseradish and cress
  • Fabacae sp. for example bean, peanuts
  • Papilionaceae sp. for example soya bean
  • Solanaceae sp. for example potatoes
  • Plants are understood here to mean all plants and plant populations, such as desired and undesired wild plants or crop plants (including naturally occurring crop plants).
  • Crop plants may be plants which can be obtained by conventional breeding and optimization methods or by biotechnological and genetic engineering methods or combinations of these methods, including the transgenic plants and including the plan cultivars which are protectable and non-protectable by plant breeders' rights.
  • Plant parts are understood to mean all parts and organs of plants above and below the ground, such as shoot, leaf, flower and root, examples of which include leaves, needles, stalks, stems, flowers, fruit bodies, fruits and seeds, and also roots, tubers and rhizomes.
  • the plant parts also include harvested material and vegetative and generative propagation material, for example cuttings, tubers, rhizomes, slips and seeds.
  • the invention furthermore includes a method for treating seed, particularly seeds (dormant, primed, pregerminated or even with emerged roots and leaves) treated with at least one of the compounds of the formula (I) and compositions thereof.
  • inventive seeds are used in methods for protection of seeds and emerged plants from the seeds from phytopathogenic harmful fungi. In these methods, seed treated with at least one inventive active ingredient is used.
  • the present invention therefore also relates to a method for protecting seeds, germinating plants and emerged seedlings against attack by animal pests, nematodes and/or phytopathogenic harmful microorganisms by treating the seeds with an inventive composition.
  • the invention also relates to the use of the compositions according to the invention for treating seeds for protecting the seeds, the germinating plants and emerged seedlings against animal pests and/or phytopathogenic microorganisms.
  • the invention further relates to seeds which have been treated with an inventive composition for protection from animal pests and/or phytopathogenic microorganisms ,
  • One of the advantages of the present invention is that the treatment of the seeds with these compositions not only protects the seed itself, but also the resulting plants after emergence, from animal pests and/or phytopathogenic harmful microorganisms. In this way, the immediate treatment of the crop at the time of sowing or shortly thereafter protect plants as well as seed treatment in prior to sowing. It is likewise considered to be advantageous that the inventive active ingredients or compositions can be used especially also for transgenic seed, in which case the plant which grows from this seed is capable of expressing a protein which acts against pests, herbicidal damage or abiotic stress. The treatment of such seeds with the inventive active ingredients or compositions, for example an insecticidal protein, can result in control of certain pests.
  • the compounds of the formula (I) are suitable for protection of seed of any plant variety which is used in agriculture, in the greenhouse, in forests or in horticulture. More particularly, the seed is that of cereals (such as wheat, barley, rye, millet and oats), oilseed rape, maize, cotton, soybeen, rice, potatoes, sunflower, beans, coffee, beet (e.g. sugar beet and fodder beet), peanut, vegetables (such as tomato, cucumber, onions and lettuce), lawns and ornamental plants. Of particulai- significance is the treatment of the seed of wheat, soybean, oilseed rape, maize and rice.
  • transgenic seed As also described below, the treatment of transgenic seed with the inventive active ingredients or compositions is of particular significance.
  • This refers to the seed of plants containing at least one heterologous gene which allows the expression of a polypeptide or protein, e.g. having insecticidal properties.
  • heterologous genes in transgenic seeds may originate, for example, from microorganisms of the species Bacillus, Rhizobium, Pseudomonas, Serratia, Trichoderma, Clavihacter, Glomus or Gliodadium.
  • These heterologous genes preferably originate from Bacillus sp., in which case the gene product is effective against the European corn borer and/or the Western com rootworm.
  • the heterologous genes originate from Bacillus thuringiensis .
  • the inventive composition is applied to seeds either alone or in a suitable formulation.
  • the seed is treated in a state in which it is sufficiently stable for no damage to occur in the course of treatment.
  • seeds can be treated at any time between harvest and some time after sowing. It is customary to use seed which has been separated from the plant and freed from cobs, shells, stalks, coats, hairs or the flesh of the fruits. For example, it is possible to use seed which has been harvested, cleaned and dried down to a moisture content of less than 15% by weight.
  • seed which, after drying, for example, has been treated with water and then dried again or seeds just after priming, or seeds stored in primed conditions or pre-germinated seeds, or seeds sown on nursery trays, tapes or paper.
  • the amount of the inventive composition applied to the seed and/or the amount of further additives is selected such that the germination of the seed is not impaired, or that the resulting plant is not damaged. This must be ensured particularly in the case of active ingredients which can exhibit phvtotoxic effects at certain application rates.
  • the compounds of the formula (I) can be applied directly, i.e. without containing any other components and without having been diluted. In general, it is preferable to apply the compositions to the seed in the form of a suitable formulation. Suitable formulations and methods for seed treatment are known to those skilled in the art.
  • the compounds of the formula (I) can be converted to the customary formulations relevant to on-seed applications, such as solutions, emulsions, suspensions, powders, foams, slurries or combined with other coating compositions for seed, such as film forming materials, pelleting materials, fine iron or other metal powders, granules, coating material for inactivated seeds, and also ULV formulations.
  • seeds can be coated with polymer.
  • the polymer coating is comprised of a binder, a wax and a pigment, and one or more stabilizers in an amount effective to stabilize the suspension.
  • the binder can be a polymer selected from the group consisting of vinyl acetate-ethylene copolymer, vinyl acetate homopolymer, vinyl acetate-acrylic copolymer, vinylacrylic, acrylic, ethylene-vinyl chloride, vinyl ether maleic anhydride, or butadiene styrene. Other similar polymers can be used.
  • formulations are prepared in a known manner, by mixing the active ingredients or active ingredient combinations with customary additives, for example customary extenders and solvents or diluents, dyes, wetting agents, dispersants, emulsifiers, antifoams, preservatives, secondary thickeners, adhesives, gibberellins, and also water.
  • customary additives for example customary extenders and solvents or diluents, dyes, wetting agents, dispersants, emulsifiers, antifoams, preservatives, secondary thickeners, adhesives, gibberellins, and also water.
  • Useful dyes which may be present in the seed dressing formulations usable in accordance with the invention are all dyes which are customary for such purposes. It is possible to use either pigments, which are sparingly soluble in water, or dyes, which are soluble in water. Examples include the dyes known by the names Rhodamine B, C.I. Pigment Red 112 and C.I. Solvent Red I.
  • Useful wetting agents which may be present in the seed dressing formulations usable in accordance with the invention are all substances which promote wetting and which are conventionally used for the formulation of active agrochemical ingredients.
  • Usable with preference are alkylnaphthaienesuiphonates, such as diisopropyl- or diisobutylnaphthalenesulphonates.
  • Useful dispersants and/or emulsifiers which may be present in the seed dressing formulations usable in accordance with the invention are all nonionic, anionic and cationic dispersants conventionally used for the formulation of active agrochemical ingredients. Usable with preference are nonionic or anionic dispersants or mixtures of nonionic or anionic dispersants.
  • Useful nonionic dispersants include especially ethylene oxide/propylene oxide block polymers, alkylphenol poiygiycol ethers and tristryrylphenol polyglycol ether, and the phosphated or sulphated derivatives thereof.
  • Suitable anionic dispersants are especially lignosulphonates, polyacrylic acid salts and arylsulphonate/formaldehyde condensates.
  • Antifoams which may be present in the seed dressing formulations usable in accordance with the invention are all foam-inhibiting substances conventionally used for the formulation of active agrochemical ingredients. Silicone antifoams and magnesium stearate can be used with preference.
  • Preservatives which may be present in the seed dressing formulations usable in accordance with the invention are all substances usable for such purposes in agrochemical compositions. Examples include dichiorophene and benzyl alcohol hemiformal.
  • Secondary thickeners which may be present in the seed dressing formulations usable in accordance with the invention are all substances usable for such purposes in agrochemical compositions.
  • Preferred examples include cellulose derivatives, acrylic acid derivatives, xanthan, modified clays and finely divided silica.
  • Adhesives which may be present in the seed dressing formulations usable in accordance with the invention are all customary binders usable in seed dressing products. Preferred examples include polyvinylpyrrolidone, polyvinyl acetate, polyvinyl alcohol and tylose.
  • the formulations for on-seed applications usable in accordance with the invention can be used to treat a wide variety of different kinds of seed either directly or after prior dilution with water.
  • the concentrates or the preparations obtainable therefrom by dilution with water can be used to dress the seed of cereals, such as wheat, barley, rye, oats, and triticale, and also seeds of maize, soybean, rice, oilseed rape, peas, beans, cotton, sunflowers, and beets, or else a wide variety of different vegetable seeds.
  • the formulations usable in accordance with the invention, or the dilute preparations thereof, can also be used for seeds of transgenic plants. In this case, additional effects may also occur in interaction with the substances formed by expression.
  • the application rate of the formulations usable in accordance with the invention can be varied within a relatively wide range. It is guided by the particular content of the active ingredients in the formulations and by the seeds.
  • the application rates of each single active ingredient are generally between 0.001 and 15 g per kilogram of seed, preferably between 0.01 and 5 g per kilogram of seed.
  • the application rates can be varied within a relatively wide range, depending on the kind of application.
  • the application rate of the inventive active ingredients is: in the case of treatment of plant parts, for example leaves: from 0.1 to 10000 g ha, preferably from 10 to 1000 g/ha, more preferably from 30 to 300 g/ha (in the case of application by watering or dripping, it is even possible to reduce the application rate, especially when inert substrates such as rockwool or perlite are used); in the case of seed treatment: from 0.1 to 10 kg per 100 kg of seed, preferably from 1 to 150 g per 100 kg of seed, more preferably from 2.5 to 25 g per 100 kg of seed, even more preferably from 2.5 to 12.5 g per 100 kg of seed; in the case of soil treatment: from 0.1 to 10000 g/ha, preferably from 1 to 5000 g/ha.
  • the compounds of the formula (I) can, at particular concentrations or application rates, also be used as herbicides, safeners, growth regulators or agents to improve plant properties, or as microbicides, for example as fungicides, antimycotics, bactericides, viricides (including compositions against yiroids) or as compositions against MLO (Mycoplasma-like organisms) and RLO (Rickettsia- like organisms).
  • Plant growth regulators may exert various effects on plants. The effect of the substances depends essentially on the time of application in relation to the developmental stage of the plant, the plant variety and also on the amounts of active ingredient applied to the plants or their environment and on the type of application. In each case, growth regulators should have a particular desired effect on the crop plants.
  • Growth regulating effects comprise earlier germination, better emergence, more developed root system and/or improved root growth, increased ability of tillering, more productive tillers, earlier flowering, increased plant height and/or biomass, shorting of stems, improvements in shoot growth, number of kernels/ear, number of ears/m 2 , number of stolons and/or number of flowers, enhanced harvest index, bigger leaves, less dead basal leaves, improved phyliotaxy, earlier maturation/ earlier fruit finish, homogenous riping, increased duration of grain filling, better fruit finish, bigger fruit/vegetable size, sprouting resistance and reduced lodging.
  • Increased or improved yield is referring to total biomass per hectare, yield per hectare, kernel/fruit weight, seed size and/or hectolitre weight as well, as to improved product quality, comprising:
  • improved marketability relating to improved fruit/grain quality, size distribution (kernel, fruit, etc.), increased storage/shelf-life, firmness /softness, taste (aroma, texture, etc.), grade (size, shape, number of berries, etc.), number of berries/fruits per bunch, crispness, freshness, coverage with wax, frequency of physiological disorders, colour, etc.:
  • Plant growth-regulating compounds can be used, for example, to slow down the vegetative growth of the plants.
  • Such growth depression is of economic interest, for example, in the case of grasses, since it is thus possible to reduce the frequency of grass cutting in ornamental gardens, parks and sport facilities, on roadsides, at airports or in fruit crops.
  • Also of significance is the inhibition of the growth of herbaceous and woody plants on roadsides and in the vicinity of pipelines or overhead cables, or quite generally in areas where vigorous plant growth is unwanted.
  • growth regulators for inhibition of the longitudinal growth of cereal. This reduces or completely eliminates the risk of lodging of the plants prior to harvest.
  • growth regulators in the case of cereals can strengthen the culm, which also counteracts lodging.
  • the employment of growth regulators for shortening and strengthening culms allows the deployment of higher fertilizer volumes to increase the yield, without any risk of lodging of the cereal crop.
  • vegetative growth depression allows denser planting, and it is thus possible to achieve higher yields based on the soil surface.
  • Another advantage of the smaller plants obtained in this way is that the crop is easier to cultivate and harvest.
  • Reduction of the vegetative plant growth may also lead to increased or improved yields because the nutrients and assimilates are of more benefi to flower and fruit formation than to the vegetative parts of the plants.
  • growth regulators can also be used to promote vegetative growth. This is of great benefit when harvesting the vegetative plant parts. However, promoting vegetative growth may also promote generative growth in that more assimilates are formed, resulting in more or larger fruits,
  • beneficial effects on growth or yield can be achieved through improved nutrient use efficiency, especially nitrogen (N)-use efficiency, phosphours (P)-use efficiency, water use efficiency, improved transpiration, respiration and/or C0 2 assimilation rate, better nodulation, improved Ca-metabolism etc.
  • nitrogen (N)-use efficiency especially nitrogen (N)-use efficiency, phosphours (P)-use efficiency, water use efficiency, improved transpiration, respiration and/or C0 2 assimilation rate, better nodulation, improved Ca-metabolism etc.
  • growth regulators can be used to alter the composition of the plants, which in turn may result in an improvement in quality of the harvested products. Under the influence of growth regulators, parthenocarpic fruits may be formed. In addition, it is possible to influence the sex of the flowers. It is also possible to produce sterile pollen, which is of great importance in the breeding and production of hybrid seed. Use of growth regulators can control the branching of the plants. On the one hand, by breaking apical dominance, it is possible to promote the development of side shoots, which may be highly desirable particularly in the cultivation of ornamental plants, also in combination with an inhibition of growth. On the other hand, however, it is also possible to inhibit the growth of the side shoots. This effect is of particular interest, for example, in the cultivation of tobacco or in the cultivation of tomatoes.
  • the amount of leaves on the plants can be controlled such that defoliation of the plants is achieved at a desired time.
  • defoliation plays a major role in the mechanical harvesting of cotton, but is also of interest for facilitating harvesting in other crops, for example in viticulture.
  • Defoliation of the plants can also be undertaken to lower the transpiration of the plants before they are transplanted.
  • growth regulators can modulate plant senescence, which may result in prolonged green leaf area duration, a longer grain filling phase, improved yield quality, etc. Growth regulators can likewise be used to regulate fruit dehiscence. On the one hand, it is possible to prevent premature fruit dehiscence. On the other hand, it is also possible to promote fruit dehiscence or even flower abortion to achieve a desired mass ("thinning"). In addition, it is possible to use growth regulators at the time of harvest to reduce the forces required to detach the fruits, in order to allow mechanical harvesting or to facilitate manual harvesting. Growth regulators can also be used to achieve faster or else delayed ripening of the harvested material before or after harvest. This is paiticulai y advantageous as it allows optimal adjustment to the requirements of the market.
  • growth regulators in some cases can improve the fruit colour.
  • growth regulators can also be used to synchronize maturation within a certain period of time. This establishes the prerequisites for complete mechanical or manual harvesting in a single operation, for example in the case of tobacco, tomatoes or coffee.
  • growth regulators By using growth regulators, it is additionally possible to influence the resting of seed or buds of the plants, such that plants such as pineapple or ornamental plants in nurseries, for example, germinate, sprout or flower at a time when they are normally not inclined to do so. in areas where there is a risk of frost, it may be desirable to delay budding or germination of seeds with the aid of growth regulators, in order to avoid damage resulting from late frosts.
  • growth regulators can induce resistance of the plants to frost, drought or high salinity of the soil. This allows the cultivation of plants in regions which are normally unsuitable for this purpose.
  • the compounds of the formula (I) also exhibit a potent strengthening effect in plants. Accordingly, they can be used for mobilizing the defences of the plant against attack by undesirable microorganisms.
  • Plant- strengthening (resistance-inducing) substances in the present context are substances capable of stimulating the defence system of plants in such a way that the treated plants, when subsequently inoculated with undesirable microorganisms, develop a high degree of resistance to these microorganisms.
  • plant physiology effects comprise the following: Abiotic stress tolerance, comprising tolerance to high or low temperatures, drought tolerance and recovery after drought stress, water use efficiency (correlating to reduced water consumption), flood tolerance, ozone stress and UV tolerance, tolerance towards chemicals like heavy metals, salts, pesticides etc.
  • Biotic stress tolerance comprising increased fungal resistance and increased resistance against nematodes, viruses and bacteria.
  • biotic stress tolerance preferably comprises increased fungal resistance and increased resistance against nematodes.
  • Increased plant vigor comprising plant health / plant quality and seed vigor, reduced stand failure, improved appearance, increased recovery after periods of stress, improved pigmentation (e.g. chlorophyll content, stay-green effects, etc.) and improved hoto synthetic efficiency.
  • the compounds of the formula (I) can reduce the mycotoxin content in the harvested material and the foods and feeds prepared therefrom.
  • Mycotoxins include particulai y, but not exclusively, the following: deoxynivalenol (DON), nivalenol, 15-Ac-DON, 3-Ac-DON, T2- and HT2-toxin, fumonisins, zearalenon, moniliformin, fusarin, diaceotoxyscirpenol (DAS), beauvericin, enniatin, fusaroproliferin, fusarenol, ochratoxins, patulin, ergot alkaloids and aflatoxins which can be produced, for example, by the following fungi: Fusarium spec, such as F.
  • verticillioides etc. and also by Aspergillus spec, such as A. flavus, A, parasiticus, A. nomius, A. ochraceus, A. clavatus, A. terreus, A. versicolor, Penicillium spec, such as P. verrucosum, P. viridicatum, P. citrinum, P. expansum, P. claviforme, P. roqueforti, Claviceps spec, such as C. purpurea, C. fusiformis, C. paspali, C. africana, Stachybotrys spec and others.
  • Aspergillus spec such as A. flavus, A, parasiticus, A. nomius, A. ochraceus, A. clavatus, A. terreus, A. versicolor, Penicillium spec, such as P. verrucosum, P. viridicatum, P. citrinum, P
  • the compounds of the formula (I) can also be used in the protection of materials, for protection of industrial materials against attack and destruction by phytopathogenic fungi.
  • the compounds of the formula (I) can be used as antifouling compositions, alone or in combinations with other active ingredients.
  • Industrial materials in the present context are understood to mean inanimate materials which have been prepared for use in industry.
  • industrial materials which are to be protected by- inventive compositions from microbial alteration or destruction may be adhesives, glues, paper, wallpaper and board/cardboard, textiles, carpets, leather, wood, fibers and tissues, paints and plastic articles, cooling lubricants and other materials which can be infected with or destroyed by microorganisms.
  • Parts of production plants and buildings for example cooling-water circuits, cooling and heating systems and ventilation and air-conditioning units, which may be impaired by the proliferation of microorganisms may also be mentioned within the scope of the materials to be protected.
  • Industrial materials within the scope of the present invention preferably include adhesives, sizes, paper and card, leather, wood, paints, cooling lubricants and heat transfer fluids, more preferably wood.
  • the compounds of the formula (I) may prevent adverse effects, such as rotting, decay, discoloration, decoloration or formation of mould.
  • the compounds of the formula (I) may also be used against fungal diseases liable to grow on or inside timber.
  • the term "timber" means all types of species of wood, and all types of working of this wood intended for construction, for example solid wood, high-density wood, laminated wood, and plywood.
  • the method for treating timber according to the invention mainly consists in contacting a composition according to the invention; this includes for example direct application, spraying, dipping, injection or any other suitable means.
  • the compounds of the formula (I) can be used to protect objects which come into contact with saltwater or brackish water, especially hulls, screens, nets, buildings, moorings and signalling systems, from fouling.
  • the compounds of the formula (I) can also be employed for protecting storage goods.
  • Storage goods are understood to mean natural substances of vegetable or animal origin or processed products thereof which are of natural origin, and for which long-term protection is desired.
  • Storage goods of vegetable origin for example plants or plant parts, such as stems, leaves, tubers, seeds, fruits, grains, can be protected freshly harvested or after processing by (pre)drying, moistening, comminuting, grinding, pressing or roasting.
  • Storage goods also include timber, both unprocessed, such as construction timber, electricity poles and barriers, or in the form of finished products, such as furniture.
  • Storage goods of animal origin are, for example, hides, leather, furs and hairs.
  • the inventive compositions may prevent adverse effects, such as rotting, decay, discoloration, decoloration or formation of mould.
  • Microorganisms capable of degrading or altering the industrial materials include, for example, bacteria, fungi, yeasts, algae and slime organisms.
  • the compounds of the formula (I) preferably act against fungi, especially moulds, wood-discoloring and wood-destroying fungi (Ascomycetes,
  • Examples include microorganisms of the following genera: Altemaria, such as Alternaria tenuis: Aspergillus, such as Aspergillus niger; Chaetomium, such as Chaetomium globosum; Coniophora, such as Coniophora puetana; Lentinus, such as Lentinus tigrinus; Penicillium, such as Penicillium glaucum; Polyporus, such as Polyporus versicolor, Aureobasidium, such as Aureobasidium pullulans; Sclerophoma, such as Sclerophoma pityophila Trichoderma, such as Trichoderma viride Qphiostoma spp., Ceratocystis spp., Humicola spp., Peiriella spp., Trichurus spp., Co
  • the compounds of the formula (I) also have very good antimycotic effects. They have a very broad antimycotic activity spectrum, especially against dermatophytes and yeasts, moulds and diphasic fungi (for example against Candida species, such as Candida albicans, Candida glahraia), and Epidermophyion floccosurn, Aspergillus species, such as Aspergillus niger and Aspergillus fumigatus, T ' richophyton species, such as Trichophyton mentagrophytes, Microsporon species such as Microsporon canis and audouinii.
  • the enumeration of these fungi by no means constitutes a restriction of the mycotic spectrum covered, and is merely of illustrative character.
  • the compounds can be used also to control important fungal pathogens in fish and Crustacea farming, e.g. saprolegnia diclina in trouts, saprolegnia parasitica in crayfish.
  • the compounds of the formula (I) can therefore be used both in medical and in non-medical applications.
  • the compounds of the formula (I) can be used as such, in the form of their formulations or the use forms prepared therefrom, such as ready-to-use solutions, suspensions, wettable powders, pastes, soluble powders, dusts and granules.
  • Application is accomplished in a customary manner, for example by watering, spraying, atomizing, broadcasting, dusting, foaming, spreading-on and the like. It is also possible to deploy the active ingredients by the ultra-low volume method or to inject the active ingredient preparation/the active ingredient itself into the soil. It is also possible to treat the seed of the plants.
  • plants and their parts in accordance with the invention, preferably with wild plant species and plant cultivars, or those obtained by conventional biological breeding methods, such as crossing or protoplast fusion, and also parts thereof.
  • transgenic plants and plant cultivars obtained by genetic engineering methods if appropriate in combination with conventional methods (Genetically Modified Organisms), and parts thereof are treated.
  • the terms "parts” or “parts of plants” or “plant parts” have been explained above. More preferably, plants of the plant cultivars which are commercially available or are in use are treated in accordance with the invention.
  • Plant cultivars are understood to mean plants which have new properties ("traits") and have been obtained by conventional breeding, by mutagenesis or by recombinant DNA techniques. They can be cultivars, varieties, bio- or genotypes.
  • the method of treatment according to the invention can be used in the treatment of genetically modified organisms (GMQs), e.g. plants or seeds.
  • Genetically modified plants are plants of which a heterologous gene has been stably integrated into genome.
  • the expression "heterologous gene” essentially means a gene which is provided or assembled outside the plant and when introduced in the nuclear, chloroplastic or mitochondrial genome gives the transformed plant new or improved agronomic or other properties by expressing a protein or polypeptide of interest or by downregulating or silencing other gene(s) which are present in the plant (using for example, antisense technology, cosuppression technology, RNA interference - RNAi - technology or microRNA - miRNA - technology).
  • a heterologous gene that is located in the genome is also called a transgene.
  • a transgene that is defined by its particular location in the plant genome is called a transformation or transgenic event.
  • Plants and plant cultivars which are preferably to be treated according to the invention include all plants which have genetic material which impart particularly advantageous, useful traits to these plants (whether obtained by breeding and/or biotechnological means). Plants and plant cultivars which are also preferably to be treated according to the invention are resistant against one or more biotic stresses, i.e. said plants show a better defense against animal and microbial pests, such as against nematodes, insects, mites, phytopathogenic fungi, bacteria, viruses and/or viroids. Plants and plant cultivars which may also be treated according to the invention are those plants which are resistan to one or more abiotic stresses.
  • Abiotic stress conditions may include, for example, drought, cold temperature exposure, heat exposure, osmotic stress, flooding, increased soil salinity, increased mineral exposure, ozone exposure, high light exposure, limited availability of nitrogen nutrients, limited availability of phosphorus nutrients, shade avoidance.
  • Plants and plant cultivars which may also be treated according to the invention are those plants characterized by enhanced yield characteristics. Increased yield in said plants can be the result of, for example, improved plant physiology, growth and development, such as water use efficiency, water retention efficiency, improved nitrogen use, enhanced carbon assimilation, improved photosynthesis, increased germination efficiency and accelerated maturation.
  • Yield can furthermore be affected by improved plant architecture (under stress and non- stress conditions), including but not limited to, early flowering, flowering control for hybrid seed production, seedling vigor, plant size, internode number and distance, root growth, seed size, fruit size, pod size, pod or ear number, seed number per pod or ear, seed mass, enhanced seed filling, reduced seed dispersal, reduced pod dehiscence and lodging resistance.
  • Further yield traits include seed composition, such as carbohydrate content and composition for example cotton or starch, protein content, oil content and composition, nutritional value, reduction in anti -nutritional compounds, improved processabiiity and better storage stability. Plants that may be treated according to the invention are hybrid plants that already express the characteristic of heterosis or hybrid vigor which results in generally higher yield, vigor, health and resistance towards biotic and abiotic stresses).
  • Plants or plant cultivars which may be treated according to the invention are herbicide-tolerant plants, i.e. plants made tolerant to one or more given herbicides. Such plants can be obtained either by genetic transformation, or by selection of plants containing a mutation imparting such herbicide tolerance.
  • Plants or plant cultivars which may also be treated according to the invention are insect-resistant transgenic plants, i.e. plants made resistant to attack by certain target insects. Such plants can be obtained by genetic transformation, or by selection of plants containing a mutation imparting such insect resistance.
  • Plants or plant cultivars obtained by plant biotechnology methods such as genetic engineering which may also be treated according to the invention are tolerant to abiotic stresses. Such plants can be obtained by genetic transformation, or by selection of plants containing a mutation imparting such stress resistance.
  • Plants or plant cultivars obtained by plant biotechnology methods such as genetic engineering which may also be treated according to the invention show altered quantity, quality and/or storage- stability of the harvested product and/or altered properties of specific ingredients of the harvested product.
  • Plants or plant cultivars which may also be treated according to the invention are plants, such as cotton plants, with altered fiber characteristics. Such plants can be obtained by genetic transformation, or by selection of plants contain a mutation imparting such altered fiber characteristics.
  • Plants or plant cultivars which may also be treated according to the invention are plants, such as oilseed rape or related Brassica plants, with altered oil profile characteristics. Such plants can be obtained by genetic transformation, or by selection of plants contain a mutation imparting such altered oil profile characteristics.
  • Plants or plant cultivars which may also be treated according to the invention are plants, such as oilseed rape or related Brassica plants, with altered seed shattering characteristics. Such plants can be obtained by genetic transformation, or by selection of plants contain a mutation imparting such altered seed shattering characteristics and include plants such as oilseed rape plants with delayed or reduced seed shattering. Plants or plant cultivars (that can be obtained by plant biotechnology methods such as genetic engineering) which may also be treated according to the invention are plants, such as tobacco plants, with altered post-translational protein modification patterns.
  • a compound of formula (5) is prepared as per the procedure reported in Med. Chem. Research, 22, 1747-1755 (2013).
  • a compound of formula (1) is reacted with compound of general formula (2) to get a compound of formula (3).
  • the compound (3) is cyelized to get a 1 ,2,3-thiadiazole derivative of formula (4).
  • the derivative (4) is hydrolysed to get a compound of formula (5).
  • the compound (5) is halogenated to get the acid chloride of formula (6),
  • the acid halide of formula (6) is reacted with an amine of the general formula (7) to get the compound of formula (8).
  • the acid of formula (5) is reacted with an amine of the general formula (7) using in the presence of suitable condensing agent to get the compound of formula (8).
  • the acid of formula (4) is reacted with an amine of the general formula (7) using in the presence of suitable condensing agent to get the compound of formula (8).
  • the amide of formula (8) is treated with suitable thionating agent to give thioamide of formula (9).
  • N-substituted formula of (7) can be prepared by known processes such as reductive animation of aldehydes or ketones (Bioorganics and Medicinal Chemistry Letters 16 (2006) 2013-2016 or reduction of imines (Tetrahedron, 61 (49), 11521-1 1764, 2005), or nucleophilc substitution of a halogen (journal of Medicinal chemistry 45 (18), 3878-3890, 2002)
  • Step A Benzyl (Z)-2-(4-ethoxy-l,l-difluoro-4-oxobutan-2-ylidene)hydrazine-l-carboxylate
  • Step D Preparation of 4-(difluoromethyl)-N-(3-(trifluoromethoxy)phenyl)-l, 2, 3- thiadiazole-5-carboxamide
  • Step-A Ethyl (Z)-2 ⁇ (4-ethoxy ⁇ l,i,l-trifluoro-4 ⁇ oxobistan ⁇ 2 ⁇ ylidene)hydrazine ⁇ l- carboxylate
  • Step-B Ethyl 4-(trifluoromethyl)-l, 2, 3-thiadiazoIe-5 ⁇ carfooxyIate
  • Step-C Preparation of N-(4-(pentafluoro- 6-sulfanyl)phenyl)-4-(trifluoromethyl)-l,2,3- thiadiazole-5-carboxamide
  • Step A 4-(difluoromethyl)-N-(4-(pentafluoro- 6-sulfanyl)phenyl)-l, 2, 3-tfaiadiazoIe- ⁇ - carboxamide
  • Step A N-(4-bromo-2-(trifluoromethyl)phenyl)-4-(difluoromethyl)-l, 2, 3-thiadiazole-5- carboxamide
  • Step B N-(4-bromo-2-(trifluoromethyl)phenyl)-4-(difluoromethyl)-N-methyl-l,2,3- thiadiazole-5-carboxamide
  • Step A 4-(difluoromethyl)-N-(3-((trifluoromethyl)thio)phenyl)-l,2,3-thiadiazole-5- carboxamide
  • Step B N-(2-Chloro-4(trifluoromethyl)sulfinyl)phenyl)-4-(difluoromethyl)-l,2,3- thiadiazole-5-carboxamide
  • Step B N-(2-Bromo-4(trifluoromethyl)thio)phenyl)-4-(difluoromethyl)-l,2,3-thiadiazole-5- carboxamide
  • Step A 3-(isopropylthio)aniline.
  • Step B 4-(difluoromethyl)-N-(3-(isopropylthio)phenyl)-l,2,3-thiadiazole-5-carboxamide
  • Step D N-(3-(N-cyanopropan-2-ylsulfonimidoyl)phenyl)-4-(difluoromethyl)-l, 2, 3- thiadiazole-5-carboxamide.
  • M+l means the molecular ion peak, plus or minus 1 a.m.u. (atomic mass unit) respectively, as observed in mass spectroscopy l H-NMR data of selected examples are written in form of ⁇ -NMR-peak lists. To each signal peak are listed the 6- value in ppm and the no of proton in round brackets.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)

Abstract

La présente invention concerne des composés de 1,2,3-thiadiazole de formule (I), formule dans laquelle R1, R2, T et Z ont les significations telles que définies dans la description. L'invention concerne en outre leur utilisation pour protéger des cultures en luttant contre des micro-organismes phytopathogènes indésirables. (I)
PCT/IB2017/057871 2016-12-21 2017-12-13 Composés de 1,2,3-thiadiazole et leur utilisation en tant qu'agent de protection des cultures Ceased WO2018116073A1 (fr)

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CN110041324A (zh) * 2019-05-17 2019-07-23 南开大学 一类噻二唑和异噻唑酰胺类衍生物及其制备方法和用途
CN111454186A (zh) * 2019-01-18 2020-07-28 山东省联合农药工业有限公司 一种含五氟硫基的芳基甲酰苯胺类化合物及其制备方法与用途
CN111454202A (zh) * 2019-01-18 2020-07-28 山东省联合农药工业有限公司 一种含五氟硫基的杂芳基甲酰苯胺类化合物及其制备方法与用途

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CN111454202A (zh) * 2019-01-18 2020-07-28 山东省联合农药工业有限公司 一种含五氟硫基的杂芳基甲酰苯胺类化合物及其制备方法与用途
CN111454202B (zh) * 2019-01-18 2021-10-01 山东省联合农药工业有限公司 一种含五氟硫基的杂芳基甲酰苯胺类化合物及其制备方法与用途
CN111454186B (zh) * 2019-01-18 2022-11-08 山东省联合农药工业有限公司 一种含五氟硫基的芳基甲酰苯胺类化合物及其制备方法与用途
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