WO2019048988A1 - Nouveaux composés hétérocycliques fongicides - Google Patents

Nouveaux composés hétérocycliques fongicides Download PDF

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Publication number
WO2019048988A1
WO2019048988A1 PCT/IB2018/056580 IB2018056580W WO2019048988A1 WO 2019048988 A1 WO2019048988 A1 WO 2019048988A1 IB 2018056580 W IB2018056580 W IB 2018056580W WO 2019048988 A1 WO2019048988 A1 WO 2019048988A1
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WIPO (PCT)
Prior art keywords
methyl
oxo
piperidin
acetyl
thiazole
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PCT/IB2018/056580
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English (en)
Inventor
Gajanan SHANBHAG
Aditya Sharma
G. Renugadevi
Jagadish Pabba
Rohit Arvind DENGALE
Dipankar Roy
Mohan Kumar S.P.
Yogesh Kashiram BELKAR
Santosh Shridhar AUTKAR
Ruchi GARG
Hagalavadi M VENKATESHA
Alexander Guenther Maria KLAUSENER
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Pi Industries Ltd.
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Publication of WO2019048988A1 publication Critical patent/WO2019048988A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
    • 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
    • A01N43/74—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 one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
    • A01N43/78—1,3-Thiazoles; Hydrogenated 1,3-thiazoles

Definitions

  • the present invention relates to novel fungicidal heterocyclic compounds and its salts, metal complexes, N-oxides, enantiomers, stereoisomers and polymorphs thereof; compositions and methods of use of the compounds for controlling or preventing phytopathogenic micro-organisms.
  • the present invention relates to a compound selected from Formula I, wherein the substituents are as defined in the description.
  • compositions comprising, “comprising”, “includes”, “including”, “has”, “having”, “contains”, “containing”, “characterized by” or any other variation thereof, are intended to cover a nonexclusive 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.
  • Stereoisomers of the present invention 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 invention.
  • one stereoisomer may be more active and/or may exhibit beneficial effects when enriched relative to the other isomer(s) or when separated from the other isomer(s). Additionally, the person skilled in the art knows processes or methods or technology to separate, enrich, and/or to selectively prepare said isomers.
  • alkyl used either alone or in compound words such as “alkylthio” or “haloalkyl” or -N(alkyl) or alkylcarbonylalkyl or alkylsuphonylamino includes straight-chain or branched Cj to C 2 4 alkyl, preferably Ci to C ) 5 alkyl, more preferably Cj to C
  • alkyl include methyl, ethyl, propyl, 1 -methylethyl, butyl, 1 -methylpropyl, 2-methylpropyl, 1 , 1 -dimethyl ethyl, pentyl, 1 -methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1 - ethylpropyl, hexyl, 1 , 1 -dimethylpropyl, 1 ,2-dimethylpropyl, 1 -methylpentyl, 2-methylpentyl, 3- methylpentyl, 4-methylpentyI, 1 , 1 -dimethyl butyl, 1 ,2-dimethylbutyl, 1 ,3-dimethylbutyl, 2,2- dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1 -ethylbutyl, 2-ethylbutyl, 1
  • 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 C 2 to C 2 4 alkenes, preferably C 2 to C 15 alkenes, more preferably C 2 to C
  • 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-methyl- l -buteny!, 3- methyl- l -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 -buten
  • 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 haloalkeny! and the like, unless defined specifically elsewhere.
  • alkynyl used either alone or in compound words includes straight-chain or branched C 2 to C 24 alkynes, preferably C 2 to C , 5 alkynes, more preferably C 2 to C ]0 alkynes, most preferably C 2 to C f) alkynes.
  • alkynes include ethynyl, 1 -propynyl, 2-propynyl, 1 -butynyl, 2- butynyl, 3-butynyl, l -methyl-2-propynyl, 1 -pentynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, l-methyl-2- butynyl, l-methyl-3-butynyl, 2-methyl-3-butynyl, 3-methyl-l-butynyl, l , ] -dimethyl-2-propynyl, 1 -ethyl -
  • 2- propynyl 1 -hexynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl, l -methyl-2-pentynyl, l-methyl-3- pentynyl, l -methyl-4-pentynyl, 2-methyl-3-pentynyl, 2-methyI-4-pentynyl, 3-methyl-l-pentynyl, 3- methyl-4-pentynyl, 4-methyl-l-pentynyl, 4-methyl-2-pentynyl, l , l -dimethyl-2-butynyl, l,l-dimethyl-3- butynyl, l,2-dimethyl-3-butynyl, 2,2-dimethyl-3-butynyl, 3,3-dimethyl-l-butynyl, l-ethyl-2-butynyl,
  • alkynyl as a part of a composite substituent, for example haloalkynyl etc., unless specifically defined elsewhere.
  • Alkynyl can also include moieties comprised of multiple triple bonds such as 2,5-hexadiynyl.
  • cycloalkyl means alkyl closed to form a ring. Representative examples include but are not l imited to cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl. This definition also applies to cycloalkyl as a part of a composite substituent, for example cycloalkylalkyl etc., unless specifically defined elsewhere.
  • cycloalkenyl means alkenyl closed to form a ring including monocyclic, partially unsaturated hydrocarbyl groups. Representative examples include but are not limited to cyclopentenyl and cyclohexenyl. This definition also applies to cycloalkenyl as a part of a composite substituent, for example cycloalkenylalkyl etc., unless specifically defined elsewhere.
  • cycloalkynyl means alkynyl closed to form a ring including monocyclic, partially unsaturated groups. This definition also applies to cycloalkynyl as a part of a composite substituent, for example cycloalkynylalkyl etc., unless specifically defined elsewhere.
  • cycloalkoxy cycloalkenyloxy
  • cycloalkoxy cycloalkenyloxy
  • Representative examples of cycloalkoxy include cyclopropyloxy, cyclopentyloxy and cyclohexyloxy. This definition also applies to cycloalkoxy as a part of a composite substituent, for example cycloalkoxy alkyl etc., unless specifically defined elsewhere.
  • halogen either alone or in compound words such as “haloalkyl”, includes fluorine, chlorine, bromine or iodine. Further, when used in compound words such as “haloalkyl”, said alkyl may be partially or fully substituted with halogen atoms which may be the same or different.
  • haloalkyl include chloromethyl, bromomethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1 -chloroethyl, 1 -bromoethyl, 1 -fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro-2- fluoroethyl, 2,2,2-trichIoroethyl, pentafluoroethyl, 1 , l -dichloi -2,2,2-trifluoroethyl, and 1 , 1 , 1 - trifluoroprop-2-
  • haloalkenyl and "haloalkyny! are defined analogously except that, instead of alkyl groups, alkenyl and alkynyl groups are present as a part of the substituent.
  • haloalkoxy means straight-chain or branched alkoxy groups where some or all of the hydrogen atoms in these groups may be replaced by halogen atoms as specified 'above.
  • Non-limiting examples of haloalkoxy include chloromethoxy, bromomethoxy, dichloromethoxy, trichloromethoxy, fiuoromethoxy, difluoromethoxy, trifluoromethoxy, chlorofluoromethoxy, dichlorofluoromethoxy, chlorodifluoromethoxy, 1 -chloroethoxy, 1 -bromoethoxy, 1 -fluoroethoxy, 2-fluoroethoxy, 2,2- difluoroethoxy, 2,2,2-trifluoroethoxy, 2-chloiO-2-fluoroethoxy, 2-chloro-2,2-difluoroethoxy, 2,2-dichloro- 2-fluoroethoxy, 2,2,2-trichloroethoxy, penta
  • haloalkylthio 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, chlorodifiuoromethylthio, 1 -chloroethylthio, 1 -bromoethylthio, 1 - fluoroethylthio, 2-fluoroethylthio, 2,2-difluoroethylthio, 2,2,2-trifluoroethylthio, 2-chloro-2- fluoroethylthio, 2-chloro-2,2-difluoro
  • haloalkylthio as a part of a composite substituent, for example haloalkylthioalkyl etc., unless specifically defined elsewhere.
  • haloalkylsulfinyl include CF 3 S(0), CC1 3 S(0), CF 3 CH 2 S(0) and CF 3 CF 2 S(0).
  • haloalkylsulfonyl 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 -NRR, wherein R can be H or any possible substituent such as alkyl.
  • carbonyl means -C(O)-
  • carbonyloxy means -OC(O)-
  • sulfinyl means S(O)
  • sulfonyl means S(0) 2 '
  • alkoxy used either alone or in compound words included Cj to C 24 alkoxy, preferably C
  • alkoxy include methoxy, ethoxy, propoxy, 1 -methyl ethoxy, butoxy, 1 -methylpropoxy, 2-methylpropoxy, 1 , 1 - dimethylethoxy, pentoxy, 1 -methylbutoxy, 2-methylbutoxy, 3 -methyl butoxy, 2,2-dimethylpropoxy, 1 - ethylpropoxy, hexoxy, 1 , 1 -dimethylpropoxy, 1 ,2-dimethylpropoxy, 1 -methylpentoxy, 2-methylpentoxy, 3-methylpentoxy, 4-methyl pentoxy, 1 , 1 -dimethylbutoxy, 1 ,2-dimethylbutoxy, 1 ,3-dimethylbutoxy, 2,2- dimethylbutoxy, 2,3-di
  • alkoxyalkyl means alkoxy substitution on alkyl .
  • alkoxyalkyl include CH 3 OCH 2 ; CH 3 OCH 2 CH 2 ; CH 3 CH 2 OCH 2 ; CH 3 CH 2 CH 2 CH 2 OCH 2 and CH 3 CH 2 OCH 2 CH 2 .
  • alkoxyalkoxy means alkoxy substitution on alkoxy.
  • alkylthio includes branched or straight-chain alkylthio moieties such as methylthio, ethylthio, propylthio, 1 -methylethylthio, butylthio, 1 -methylpropylthio, 2-methylpropylthio, 1 , 1 -dimethylethylthio, pentylthio, 1 -methylbiitylthio, 2-methylbutylthio, 3-methylbutylthio, 2,2-dimethylpropylthio, 1 - ethylpropylthio, hexylthio, 1 , 1 -dimethylpropylthio, 1 ,2-dimethylpropylthio, 1 -methylpentylthio, 2- methylpentylthio, 3-methylpentylthio, 4-methylpentylthio, 1 , 1 -dimethylbutylthio, 1 ,2-dimethylbutylthio
  • halocylcoalkyl halocylcoalkenyl
  • alkylcycloalkyl cycloalkylalkyl
  • cycloalkoxyalkyl alkylsulfinylalkyl
  • alkylsulfonylalkyl alkylsulfonylalkyl
  • haloalkylcarbonyl alkylcarbonyl
  • alkylthioalkyl means alkylthio substitution on alkyl.
  • alkylthioalkyl 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 ; CH 3 CH 2 SCH 2 CH 2 and the like or different isomers.
  • alkylthioalkoxy denotes alkylthio substitution on alkoxy.
  • cycloalkylalkylamino denotes cycloalkyi substitution on alkyl amino.
  • alkoxyalkoxyalkyl is defined analogously to “alkylthioalkyl” or cycloalkylalkylamino.
  • alkoxycarbonyl is an alkoxy group bonded to a skeleton via a carbonyl group (-CO-). This definition also applies to alkoxycarbonyl as a part of a composite substituent, for example cycloalkylalkoxycarbonyl and the like, unless specifically defined elsewhere.
  • alkoxycarbonylalkylamino means alkoxy carbonyl substitution on alkyl amino.
  • alkylcarbonylalkylamino means alkyl carbonyl substitution on alkyl amino.
  • alkylthioalkoxycarbonyl, cycloalkylalkylaminoaikyl and the like are defined analogously.
  • alkylsulfinyl means alkyl substitution on sulfinyl group.
  • Non-l imiting examples of “alkylsu!finyl” include ; methylsulphinyl; ethylsulphinyl; propylsulphinyl; 1 -methylethylsulphinyl; butylsulphinyl ; 1 -methylpropylsulphinyl ; 2-methylpropylsulphinyl; 1 , 1 -dimethylethylsulphinyl; pentylsulphinyl ; 1 -methylbutylsu!phinyl ; 2-methylbutylsulphinyl; 3-methylbutylsulphinyl ; 2,2- dimethyl propylsulphinyl; l -ethylpropylsulphinyl; hexylsulphinyl; 1 , 1 -dimethyIpropyIsulphinyl
  • arylsulfinyl i ncludes Ar-S(O), wherein Ar can be any carbocyle or heterocyicle. This definition also applies to alkylsulfinyl as a part of a composite substituent, for example haloalkylsulfinyl etc., unless specifically defined elsewhere.
  • alkyl sulfonyl means alkyl substitution on sulfonyl group. Non-limiting examples of "alkylsulfonyl” include methylsulphonyl; ethylsulphonyl; propylsulphony!
  • alkylamino dialkylamino
  • l ike l ike
  • Carbocycle or carbocyclic includes “aromatic carbocyclic ring system” and “nonaromatic carbocylic ring system” or polycyclic or bicyclic (spiro, fused, bridged, nonfused) ring compounds in which ring may be aromatic or non-aromatic (where aromatic indicates that the Hueckel rule is satisfied and non-aromatic indicates that the Hueckel 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 heteroatoms independently selected from the group comprising of nitrogen, oxygen, sulfur, etc.
  • hetero in connection with atom refer to an atom independently selected from nitrogen, sulfur, oxygen, etc.
  • non-aromatic heterocyle includes fused or unfused three- to fifteen-membered, preferably three- to tweleve-membered, saturated or fully or partially unsaturated heterocycle, monocyclic or polycyclic (spiro, fused, bridged, nonfused) heterocycle wherein heteroatom is selected from the group of oxygen, nitrogen and sulphur; and if the ring contains more than one oxygen atom, they are not directly adjacent;
  • Non-limiting examples of non-aromatic heterocyle include oxetanyl, oxiranyl; aziridinyl; thi iranyl, azetidinyl, thiethanyl, dithiethanyl, diazetidinyl, 2-tetrahydrofuranyl; 3-tetrahydrofuranyl; 2- tetrahydrothienyl; 3-tetrahydrothienyl; 2-pyrrolidinyl; 3-pyrrolidinyl; 3-is
  • aromatic heterocycle or heteroaryi includes fused or unfused three to fifteen membered, preferably three to tweleve membered, more preferably 5 or 6 membered; monocyclic or polycyclic unsaturated ring system, containing heteroatoms selected from the group of oxygen, nitrogen, sulphur, etc.
  • Non-limiting examples of 5 membered heteroaryi groups include fury], thienyl, pyrrolyl, isoxazo!yl, isothiazolyl, pyrazolyl, oxazolyl, thiazolyl, imidazolyl, 1,2,4-oxadiazolyl, 1,2,4-thiadiazolyl, 1,2,4-triazolyl, 1,3,4-oxadiazolyl, 1,3,4-thiadiazolyl, 1,3,4-triazolyl, tetrazolyl; nitrogen-boiided 5-membered heteroaryi containing one to four nitrogen atoms, or benzofused nitrogen-bonded 5-membered heteroaryi containing one to three nitrogen atoms: 5-membered heteroaryi groups which, in addition to carbon atoms, may contain one to four nitrogen atoms or one to three nitrogen atoms as ring members and in which two adjacent carbon ring members or one nitrogen and one adjacent carbon ring member may be bridged by a buta-
  • Non-limiting examples of 6 membered heteroaryi groups include 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; l,2,4,5-tetrazin-3-yl and the like.
  • Non-limiting examples of benzofused 5-membered heteroaryi include indol-l-yl ; indol-2-yl; indol-3-yl; indol-4-yl; indol-5-yl; indol-6-yl; indol-7-yl; benzimidazol-l-yl; benzimidazol-2-yl ; benzimidazol-4-yl; benzimidazol-5-yl; indazol-l-yl; indazol-3-yl; indazol-4-yl; indazol-5-yl ; indazol-6-yl ; indazol-7-yl; indazol-2-yl; l-benzofuran-2-yl; l-benzofuran-3-yl; l-benzofuran-4-yl; l-benzofuran-5-yl; 1 -benzofuran- 6- yl
  • Non-limiting examples of benzofused 6-membered heteroaryi include quinol in-2-yl; quinolin-3-yl; quinolin-4-yl; quinolin-5-yl; quinolin-6-yl; quinolin-7-yl ; quinolin-8-yl; isoquinolin-l-yl; isoquinolin-3-yl; isoquinolin-4-yl ; isoquinolin-5-yl ; isoquinolin-6-yl; isoquinolin-7-yl ; isoquinolin-8-yl and the like.
  • This definition also applies to heteroaryl as a part of a composite substituent, for example heteroarylalkyl etc., unless specifically defined elsewhere.
  • alkylsilyl means branched and/or straight-chain alkyl radicals attached to a silicon atom.
  • alkylsilyl include trimefhylsilyl, triethylsilyl, t-butyl-dimethylsilyl and the like or different isomers.
  • haloalkylsilyl means at least one alkyl radicals of alkylsilyl is partially or fully substituted with halogen atoms which may be the same or different.
  • alkoxyalkylsilyl denotes at least one alkyl radical of alkylsilyl is substituted with one or more alkoxy radicals which may be the same or different.
  • alkylsilyloxy denotes an alkylsilyl moiety attached through oxygen.
  • alkyl carbonyl means alkyl group substituted on the carbonyl group. Non-limiting examples of “alkylcarbonyl” include C(0)CH 3 , C(0)CH 2 CH 2 CH 3 and C(0)CH(CH 3 ) 2 .
  • alkoxycarbonyl means alkoxy group substituted on the carbonyl group.
  • alkylaminocarbonyl means alkylamino substituted on the carbonyl group.
  • dialkylaminocarbonyl means dialkylam ino substituted on the carbonyl group.
  • haloalkylsufonylaminocarbonyl alkylsulfonylaminocarbonyl
  • alkyithioalkoxycarbonyl alkoxycarbonylalkylamino
  • the total number of carbon atoms in a substituent group is indicated by the "Q to C " prefix wherein i and j are numbers from 1 to 21.
  • C r C 3 alky!sulfonyl designates methylsulfonyl through propylsulfonyl
  • C 2 alkoxyalkyl designates CH 3 OCH 2
  • C 3 alkoxyalkyl designates, for example, CH 3 CH(OCH 3 ), CH 3 OCH 2 CH 2 or CH 3 CH 2 OCH 2
  • 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 CFI 2 CH 2 OCH 2 and CH 3 CH 2 OCH 2 CH 2 .
  • all substituents are attached to these rings through any avai lable carbon or nitrogen by replacement of a hydrogen on said carbon or nitrogen.
  • the substituents may be optional ly further substituted.
  • any deviation from such numerical values shall stil l fall within the scope of the present invention if that deviation fol lows the same scientific principle as that of the present invention.
  • the term "pest” for the purpose of the present invention includes but is not limited to fungi, stramenopiles (oomycetes), bacteria, nematodes, mites, ticks, insects and rodents.
  • the term "plant” is understood here to mean al l plants and plant populations, such as desired and undesired wi ld plants or crop plants (including naturally occurring crop plants). Crop plants may be plants which can be obtained by conventional breeding and optimization methods or by biotechnological and genetic engineering methods or combinations of these methods, including the transgenic plants and including the plant cultivars which are protectable and non-protectable by plant breeders' rights.
  • plant includes a living organism of the kind exemplified by trees, shrubs, herbs, grasses, ferns, and mosses, typically growing in a site, absorbing water and required substances through its roots, and synthesizing nutrients in its leaves by photosynthesis.
  • plant for the purpose of the present invention include but are not limited to agricultural crops such as wheat, rye, barley, triticale, oats or rice; beet, e.g. sugar beet or fodder beet; fruits, such as pomes, stone fruits or soft fruits, e.g.
  • the plant for the purpose of the present invention include but is not limited to cereals, corn, rice, soybean and other leguminous plants, fruits and fruit trees, grapes, nuts and nut trees, citrus and citrus trees, any horticultural plants, cucurbitaceae, oleaginous plants, tobacco, coffee, tea, cacao, sugar beet, sugar cane, cotton, potato, tomato, onions, peppers and vegetables, ornamentals, any floricultural plants and other plants for use of human and animals.
  • plant parts is understood to mean all parts and organs of plants above and below the ground.
  • plant parts includes but is not limited to cuttings, leaves, twigs, tubers, flowers, seeds, branches, roots including taproots, lateral roots, root hairs, root apex, root cap, rhizomes, slips, shoots, fruits, fruit bodies, bark, stem, buds, auxil obviouslyy buds, meristems, nodes and internodes.
  • locus thereof includes soil, surroundings of plant or plant parts and equipment or tools used before, during or after sowing/planting a plant or a plant part.
  • Appl ication of a compound or compounds of the present invention or the compound of the present invention in a composition optionally comprising at-least one other active compatible compound to a plant or a plant material or locus thereof include application by a technique known to a person skilled in the art which include but is not limited to spraying, coating, dipping, fumigating, impregnating, injecting and dusting.
  • adhered means adhered to a plant or plant part either physically or chemically.
  • the present invention relates to a compound selected from Formula I,
  • the present invention is inclusive of salts, metal complexes, N-oxides, isomers, and polymorphs of compound of Formula I, wherein
  • E is a fragment selected from the group consisting of E- 1 to E-5:
  • E is E-1 .
  • T 1 , T 2 T “ ' and T 4 are independently selected from 5- or 6- membered aryl ring or 5- or 6-membered saturated or partially saturated cyclic ring or 5- or 6- membered heteroaryl ring or 5- or 6-membered saturated or partially saturated heterocyclic ring, wherein each ring member of heteroaryl ring is selected from C, N, O and S, and wherein each ring member of heterocyclic ring is selected from C, N, O, S(0).
  • T 1 , T 2 , T 3 and T 4 are optionally substituted by one or more R 1 on C atoms and one or more R 2 on hetero atoms.
  • T 1 Non-limiting representative examples of T 1 are depicted herein below.
  • T 2 ? T 3 and T 4 are independently selected from C r C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C r C 6 haloalkyl, C 2 -Q, haloalkenyl, C 2 -C 6 haloalkynyl, C 3 -C 8 cycloalkyl, C 3 -C 8 halocycloalkyl, C r C 6 alkyl C 3 -C 8 cycloalkyl, C 3 -C 8 cycloalkyl C r C 6 alkyl, C 3 -C 8 cycloalkyl C 3 -C 8 cycloalkyl, C 3 -C 8 halocycloalkyl C
  • A is C(R 4 ) 2 or NR 5 .
  • Z is C or N. In one of the preferred embodiments Z is C.
  • the substitutent R 3 is selected from hydrogen, halogen, cyano, hydroxy, amino, aldehyde, carboxylic acid, C r C 6 alkyl, C 2 -C 5 alkenyl, C 2 -C 6 alkynyl, C ,-C 6 haloalkyl, C 2 -C 6 haloalkenyl, C 2 -C 6 haloalkynyl, C 3 -C 6 cycloalkyl, C 3 -C 6 halocycloalkyi, C C 6 alkyl C -C 6 cycloalkyl, C : ,-C 6 cycloalkyl C C 6 alkyl, C 3 -C 6 halocycloalkyi C
  • R 3 is selected from hydrogen, C r C 4 alkyl, C 2 -C 4 alkenyl, C 2 -C 4 alkynyl, C r C 4 haloalkyl, C,-C 4 alkoxy, halogen, cyano and hydroxy.
  • G is selected from optionally substituted G l to G63, each substituent selected from R 3a on carbon ring members and R l la on nitrogen ring members.
  • G l to G63 are as depicted herein below:
  • R 3a and R l la may be attached to one or more possible position/s.
  • the substituent R 3a is hydrogen or R 3b .
  • the substituent R 3b is a phenyl or 5- or 6-membered heteroaryl ring optionally substituted with one or more substituents independently selected from R 4a on carbon ring members and R b on nitrogen ring members.
  • R 31 ' is independently C C 3 alkyl, C r C 3 haloalkyi or halogen.
  • the substituent R' ,a is independently selected from C r C 6 alkyl, C 2 -Q, alkenyl, C 2 -C 6 alkynyl, C 3 - C 6 cycloalkyl, C 3 -C 6 cycloalkyl C r C 6 alkyl, C r C 6 alkyl C 3 -C 6 cycloalkyl, C ,-C 6 haloalkyi C 3 -C 6 cycloalkyl, C r C 6 haloalkyi, C 2 -C 6 haloaikenyl, C 2 -C 6 haloalkynyl, C 3 -C 6 halocycloalkyl, halogen, hydroxy, amino, cyano, nitro, C r C 6 alkoxy, C r C 6 haloalkoxy, C r C 6 alkylthio, C r C 6 alkylsulfinyl, C r C 6 alkylsul
  • the substituent R 4b is independently selected from C r C b alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 3 - C 6 cycloalkyl, Ci-C 6 haloalkyi, C 2 -C 6 haloaikenyl, C 2 -C 6 haloalkynyl, C 3 -C 6 halocycloalkyl and Cj-C 6 alkoxy C C 6 alkyl.
  • the substituent R l i a is hydrogen or R l lb and the substituent R i l b is independently C C 3 alkyl, C 2 - C c alkenyl, C 2 -C alkynyl, C 3 -C 6 cycloalkyl, C C 6 haloalkyi, C 2 -C 6 haloaikenyl, C 2 -C 6 haloalkynyl, C 3 - C 6 halocycloalkyl and C r C 6 alkoxy C
  • J is selected from fragments of Formula II & III
  • L 6 and L 7 together with the atoms to which they are attached may form a 4- to 7- membered carbocycl ic or heterocycl ic ring or ring system.
  • the substituent R n together with L 6 or L 7 or G or Q or R 12 or R 13 or R 14 or R 15 may form a 4- to 7- membered carbocyclic or heterocyclic ring or ring system.
  • m is an integer 0 to 1 ;
  • Q is independently phenyl, benzyl, naphthalenyl, a 5- or 6- membered aryl ring, an 8- to 1 1 - membered aryl multi-cyclic ring system, an 8- to 1 1 - membered aryl fused ring system, a 5- or 6- membered heteroaryl ring, an 8- to 1 1 - membered heteroaryl multi-cyclic ring system or an 8- to 1 1 - membered heteroaryl fused ring system, each ring member of the ring or the ring system is selected from C, N, O and S, and each ring or ring system is optionally substituted with R 14 on carbon atoms and R 15 on hetero atoms.
  • Q is selected from Q l to Q99 and the presentation " " is a single or a double bond.
  • the substituent R 14 may be attached to one or more position/s. ⁇
  • R 1 , R 2 , R 6 , R 7 , R 8 , R 9 , R i0 , R 14 , R 15 , R 18 , R 19 , R 20 , R 2 ', R 2 " and R 27 are independently selected from hydrogen, halogen, hydroxy, cyano, nitro, C r C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C C 6 haloalkyl, C 2 -C ⁇ , haioalkenyl, C 2 -C 6 haloa!kynyl, C 3 -C 8 cycloalkyl, C 3 -C 8 halocycloaikyl, Ci-C 6 alkyl C 3 -C 8 cycloalkyl, C -C 8 cycloalkyl C r C 6 alkyl, C 3 -C 8 cycloalkyl C 3 -C 8 cycloalkyl, C 3 -C 8
  • R 16 and R 17 are independently selected from C r C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 3 -C 6 cycloalkyl, C 3 -C 6 halocycloalkyl, C 3 -C 6 cycloalkyl C C 6 alkyl, C r C 6 alkyl C 3 -C 6 cycloalkyl, C,-C 6 haloalkyl C 3 -C 6 cycloalkyl, C r C 6 haloalkyl, C r C 6 alkoxy and C r C 6 haloalkoxy.
  • W is O or S. Preferably W is O.
  • L 1 is a direct bond or O or S or NR 23 .
  • R 4 , R 12 , and R 22 are independently selected from hydrogen, halogen, cyano, hydroxy, aldehyde, C,-C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C,-C 6 haloalkyl, C -C 6 haloalkenyl, C 2 - C 6 haloalkynyl, C r C 6 alkoxy C r C 6 alkyl, C r C 6 alkylthio C r C 6 alkyl, C r C 6 alkylsulfinyl C C 6 alkyl, C,- C alkylsulfonyl C -C b alkyl, C r C 6 alkylcarbonyl, C r C 6 haloalkylcarbonyl, C
  • R 5 , R 13 , and R 23 are independently selected from hydrogen, C r C6 alkyl, C?-C ( , alkenyl, C 2 -C 6 alkynyl, C r C 6 haloalkyl, C 2 -C 6 haloalkenyl, C 2 -C 6 haloalkynyl, C r C 6 alkoxy C
  • the presentation " " in ring D is a single bond when Z is N. Further, the presentation “ “ “ in ring D is a single or double bond when Z is C. In one of the preferred embodiment, the presentation " " is a single bond.
  • n is an integer ranging from 0 to 9 with a proviso that when Z is N, "n” is an integer ranging from 0 to
  • a is independently 0, 1 or 2.
  • the novel and inventive compounds of the present invention, the salts, isomers, metal complexes, N- oxides and polymorphs thereof are effective in preventing against and controlling phytopathogenic microorganisms.
  • An anion part of the salt in case the compound of Formula I is cationic or capable of forming a cation can be inorganic or organic.
  • a cation part of the salt in case the compound of Formula I is anionic or capable of forming an anion can be inorganic or organic.
  • inorganic anion part of the salt examples include but are not limited to chloride, bromide, iodide, fluoride, sulphate, phosphate, nitrate, nitrite, hydrogen carbonates and hydrogen sulphate.
  • organic anion part of the salt examples include but are not l imited to formate, alkanoates, carbonates, acetates, trifluoroacetate, trichloroacetate, propionate, glycolate, thiocyanate, lactate, succinate, malate, citrates, benzoates, cinnamates, oxalates, alkylsulphates, alkylsulphonates, arylsulphonates aryldisulphonates, alkylphosphonates, arylphosphonates, aryldiphosphonates, p-toluenesulphonate, and salicylate. ;
  • Examples of inorganic cation part of the salt include but are not limited to alkal i and alkaline earth metals.
  • Examples of organic cation part of the salt include but are not limited to pyridine, methyl amine, imidazole, benzimidazole, histidine, phosphazene, tetramethyl ammonium, tetrabutyl ammonium, choline and trimethyl amine.
  • Metal ions in metal complexes of the compound of Formula I are especially the ions of the elements of the second main group, especially calcium and magnesium, of the third and fourth main group, especially aluminium, tin and lead, and also of the first to eighth transition groups, especially chromium, manganese, iron, cobalt, nickel, copper, zinc and others. Particular preference is given to the metal ions of the elements of the fourth period and the first to eighth transition groups.
  • the metals can be present in the various valencies that they can assume.
  • Non-crystalline forms include embodiments which are solids such as waxes and gums as well as embodiments which are liquids such as solutions and melts.
  • Crystalline forms include embodiments which represent essentially a single crystal type and embodiments which represent a mixture of polymorphs (i.e. different crystalline types).
  • polymorph refers to a particular crystalline form of a chemical compound that can crystallize in different crystalline forms, these forms having different arrangements and/or conformations of the molecules in the crystal lattice.
  • polymorphs can have the same chemical composition, they can also differ in composition due the presence or absence of co-crystallized water or other molecules, which can be weakly or strongly bound in the lattice. Polymorphs can differ in such chemical, physical and biological properties as crystal shape, density, hardness, color, chemical stability, melting point, hygroscopicity, suspensibility, dissolution rate and biological availability.
  • beneficial effects e.g., suitability for preparation of useful formulations, improved biological performance
  • the present invention further relates to a process for preparing the compound of Formula I.
  • the process comprises a step of reacting JQ- 1 with a compound of Formula 5 to obtain a compound of Formula 4.
  • the compound of Formula 4 upon deprotecting provides a compound of Formula 2 which is reacted with E- 1 A to obtain the compound of Formula I;
  • W is O or S; R", G, Q and T 1 are as defined herein above.
  • W is O or S; R 1 1 , G, Q and T 1 are as defined herein above.
  • the present invention also relates to the following intermediates 4 and 2 which are useful in the synthesis of the compound of Formula 1 : wherein, R " , G, L 6 , and Q are as defined herein above.
  • the present invention also relates a composition comprising the compound of Formula 1 and one or more excipient.
  • the compound of Formula I of the present invention in the composition can be an agriculturally acceptable salt, metal complex, constitutional isomer, stereo-isomer, diastereoisomer, enantiomer, chiral isomer, atropisomer, conformer, rotamer, tautomer, optical isomer, geometric isomer, polymorph, or N- oxide thereof.
  • the excipient may be an inert carrier or any other essential ingredient such as surfactants, additives, solid diluents and liquid diluents.
  • composition of the present invention may additionally comprise at least one active compatible compound selected from fungicides, insecticides, nematicides, acaricides, biopesticides, herbicides, plant growth regulators, antibiotics, fertilisers and nutrients.
  • active compatible compounds selected from fungicides, insecticides, nematicides, acaricides, biopesticides, herbicides, plant growth regulators, antibiotics, fertilisers and nutrients.
  • the concentration of the compound of Formula I in the composition of the present invention 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 known and reported active compounds such as fungicides, insecticides, nematicides, acaricides, biopesticides, herbicides, plant growth regulators, antibiotics and nutrients can be combined with at least one compound of Formula I of the present invention.
  • active compounds such as fungicides, insecticides, nematicides, acaricides, biopesticides, herbicides, plant growth regulators, antibiotics and nutrients
  • fungicides, insecticides, nematicides, acaricides, biopesticides, herbicides, plant growth regulators, antibiotics, fertilizers and nutrients disclosed and reported in WO201776739 (A to O) can be combined with compound of Formula I of the present invention.
  • the present invention also relates to such combinations comprising the compound of the present invention and active compatible compounds reported in WO201776739.
  • fungicides insecticides, nematicides, acaricides, biopesticides, herbicides, plant growth regulators, antibiotics, fertilizers and nutrients reported in WO201776739, are not reproduced herein for the sake of brevity and are incorporated herein by way of reference as non-limiting examples to be combined with at least one compound of Formula I of the present invention.
  • the present invention also relates to a use of the compound of Formula 1 or the combination comprising the compound of Formula I or the composition comprising the compound of Formula I for controlling or preventing phytopathogenic micro-organisms such as fungi, stramenopiles, bacteria, insects, nematodes, trematodes, and mites in agricultural crops and or horticultural crops.
  • the present invention also relates to a use of the compound of Formula I or the combination or the composition for control ling or preventing phytopathogenic micro-organisms in agricultural crops and or horticulture crops.
  • the compound of Formula I or the combination or the composition of the present invention may be used to treat several fungal pathogens.
  • pathogens of fungal diseases which can be treated in accordance with the invention include:
  • 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
  • Blumeria species for example Blumeria graminis
  • Podosphaera species for example Podosphaera leucotricha
  • Sphaerotheca species for example Sphaerotheca fuliginea
  • Uncinula species for example Uncinula necator
  • Erysiphe species for example Erysiphe cichoracearu
  • Gymnosporangium species for example Gymnosporangium sabinae
  • Hemileia species for example Hemileia vastatrix
  • Phakopsora species for example Phakopsora pachyrhizi or Phakopsora meibomiae
  • Puccinia species for example Puccinia recondita, Puccinia graminis oder Puccinia striiformis
  • Uromyces species for example Uromyces appendiculatus
  • 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 Ustilago nuda
  • Seed- and soil-borne rot and wilt diseases, and also diseases of seedlings caused, for example, by Alternaria species, for example Alternaria brassicicola; Aphanomyces species, for example Aphanomyces euteiches; Ascochyta species, for example Ascochyta lentis; Aspergillus species, for example Aspergillus flavus; Cladosporium species, for example Cladosporium herbarum; Cochliobolus species, for example Cochliobolus sativus (conidial form: Drechs!era, Bipolaris Syn: Helminthosporium); Colletotrichiim species, for example Colletotrichiim coccodes; Fusarium species, for example Fusarium culmorum; Gibberella species, for example Gibberella zeae; Macrophomirta species, for example Macrophomina phaseolina; Microdochium species, for example Microdochium nivale; Monographella species,
  • Botrytis species for example Botrytis cinerea
  • Rhizoctonia species for example Rhizoctonia solani
  • Helminthosporium species for example Helminthosporium solani
  • Xanthomonas species for example Xanthomonas campestris pv. oryzae
  • Pseudomonas species for example Pseudomonas syringae pv.
  • 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), Ribesioidae 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.
  • Rosaceae sp for example pome fruits such as apples, pears, apricots, cherries, almonds and peaches
  • Ribesioidae sp. Juglandaceae sp.
  • Sterculiceae 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. for example lettuce
  • Umbelliferae sp. for example lettuce
  • Alliaceae sp. for example leek, onion
  • Papilionaceae sp. for example peas
  • major crop plants such as PoaceaelGramineae sp.
  • 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), Chenopodiaceae sp.
  • the agricultural or horticulture crops are wheat, rye, barley, triticale, oats or rice; beet, e.g. sugar beet or fodder beet; fruits, such as pomes, stone fruits or soft fruits, e.g.
  • the agriculture or horticulture 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, other vegetables and ornamentals.
  • the present invention further relates to the use of the compound of Formula I or the combination comprising the compound of Formula I or the composition comprising the compound of Formula I for treating seeds with the purpose of protecting the seeds, the germinating plants and emerged seedlings against phytopathogenic micro-organisms.
  • the present invention further relates to seeds which have been treated with the compound of Formula I or the combination comprising the compound of Formula I or the composition comprising the compound of Formula 1 for protection from phytopathogenic micro-organisms.
  • the present invention also relates to a method of controlling or preventing infestation of useful plants by phytopathogenic micro-organisms in agricultural crops and or horticultural crops wherein the compound of Formula I or the combination comprising the compound of Formula I or the composition comprising the compound of Formula I, is applied to the plants, to parts thereof or the locus thereof.
  • the effective amount of compound of Formula I ranges from 1 to 5000 gai per hectare.
  • the present invention relates to the compound of Formula I or the combination comprising the compound of Formula I or the composition comprising the compound of Formula I applied to a plant, plant parts or locus thereof.
  • the present invention furthermore includes a method for treating seed, particularly seeds (dormant, primed, pregerminated or even with emerged roots and leaves) treated with the compound of Formula I or the combination comprising the compound of Formula I or the composition comprising the compound of Formula 1.
  • seed particularly seeds (dormant, primed, pregerminated or even with emerged roots and leaves) treated with the compound of Formula I or the combination comprising the compound of Formula I or the composition comprising the compound of Formula 1.
  • the compound of Formula I or the combination comprising the compound of Formula I or the composition comprising the compound of Formula I is applied to the seeds of plants for controll ing or preventing infestation of useful plants by phytopathogenic micro-organisms in agricultural and or horticultural corps.
  • methods for the treatment of seed should also take into consideration the intrinsic phenotypes of transgenic plants in order to achieve optimum protection of the seed and the germinating plant with a minimum of crop protection compositions being employed.
  • One of the advantages of the present invention is that the treatment of the seeds with the compound of Formula I or the combination comprising the compound of Formula I or the composition comprising the compound of Formula I not only protects the seed itself, but also the resulting plants after emergence, from animal pests and/or phytopathogenic harmful micro-organisms. 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 compound of Formula I or the combination comprising the compound of Formula I or the composition comprising the compound of Formula 1 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 compound of Formula I or the combination comprising the compound of Formula I or the composition comprising the compound of Formula I is 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 particular significance is the treatment of the seed of wheat, soybean, oilseed rape, maize and rice.
  • cereals such as wheat, barley, rye, millet and oats
  • oilseed rape e.g. sugar beet and fodder beet
  • peanut e.g. sugar beet and fodder beet
  • vegetables such as tomato, cucumber, onions and lettuce
  • transgenic seed with the compound of Formula I or the combination comprising the compound of Formula I or the composition comprising the compound of Formula I, is of particular significance.
  • heterologous genes in transgenic seeds may originate, for example, from microorganisms of the species of Bacillus, Rhizobium, Pseudomonas, Serratia, Trichoderma, Clavibacter, Glomus or Gliocladium.
  • 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 corn rootworm.
  • the heterologous genes originate from Bacillus thuringiensis.
  • the compound of Formula I or the combination comprising the compound of Formula I or the composition comprising the compound of Formula I is applied to seeds.
  • 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 compound of Formula I or the combination comprising the compound of Formula I or the composition comprising the compound of Formula I appl ied 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.
  • the compound of Formula I or the combination comprising the compound of Formula I or the composition comprising the compound of 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 comprising compounds of Formula I 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 compound of 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 comprising of vinyl acetate-ethylene copolymer, vinyl acetate homopolymer, vinyl acetate-acrylic copolymer, vinylacryl ic, acrylic, ethylene-vinyl chloride, vinyl ether maleic anhydride, or butadiene styrene. Other simi lar 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 di luents, dyes, wetting agents, dispersants, emulsifiers, antifoams, preservatives, secondary thickeners, adhesives, gibberel lins, and also water.
  • customary additives for example customary extenders and solvents or di luents, dyes, wetting agents, dispersants, emulsifiers, antifoams, preservatives, secondary thickeners, adhesives, gibberel lins, 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 1 12 and C.I. Solvent Red 1 .
  • 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 alkylnaphthalenesulphonates, 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 polyglycol 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 dichlorophene and benzyl alcohol hemi formal.
  • 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 triticaie, 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, enhanced effects may also occur in interaction with the substances formed by expression.
  • all mixing units usable customarily for on-seed applications are useful. Specifically, the procedure in on-seed applications is to place the seeds into a mixer, to add the particular desired amount of the formulations, either as such or after prior dilution with water, and to mix everything until all applied formulations are distributed homogeneously on the seeds. If appropriate, this is followed by a drying operation.
  • 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 1 5 gai per kilogram of seed, preferably between 0.01 and 5 gai per kilogram of seed.
  • the application rate of the compound of Formula I or the combination comprising the compound of Formula I or the composition comprising the compound of Formula I is: in the case of treatment of plant parts, for example leaves: from 0. 1 to 10000 gai/ha, preferably from 5 to 1000 gai/ha, more preferably from 5 to 100 gai/ha (in the case of application by watering or dripping, it is even possible to reduce the application rate, especial ly when inert substrates such as rockwool or perlite are used); in the case of seed treatment: from 0.
  • the compound of Formula I may, at particular concentrations or appl ication rates, also be used as safeners, growth regulators or agents to improve plant properties, or as microbicides, for example as fungicides, antimycotics, bactericides, viricides (including compositions against viroids) or as compositions against phytoplasmas MLO (Mycoplasma-like organisms) and RLO (Rickettsia-like organisms).
  • the compound of Formula I may intervene in physiological processes of plants and can therefore also be used as plant growth regulators.
  • 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 phyllotaxy, 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 processabil ity relating to size distribution (kernel, fruit, etc.), homogenous riping, grain moisture, better milling, better vinification, better brewing, increased juice yield, harvestability, digestibility, sedimentation value, falling number, pod stability, storage stability, improved fiber length/strength/uniformity, increase of milk and/or meet quality of silage fed animals, adaption to cooking and frying; further 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.; further comprising increased desired ingredients
  • protein content protein content, fatty acids, oil content, oil quality, aminoacid composition, sugar content, acid content (pH), sugar/acid ratio (Brix), polyphenols, starch content, nutritional quality, gluten content/index, energy content, taste, etc.; and further comprising decreased undesired ingredients such as e.g. less mycotoxines, less aflatoxines, geosmin level, phenolic aromas, lacchase, polyphenol oxidases and peroxidases, nitrate content etc.
  • decreased undesired ingredients such as e.g. less mycotoxines, less aflatoxines, geosmin level, phenolic aromas, lacchase, polyphenol oxidases and peroxidases, nitrate content 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 benefit 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, especial ly 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 qual ity 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.
  • growth regulators can control the branching of the plants.
  • 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.
  • side shoots which may be highly desirable particularly in the cultivation of ornamental plants, also in combination with an inhibition of growth.
  • 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 particularly advantageous as it allows optimal adjustment to the requirements of the market. Moreover, growth regulators in some cases can improve the fruit colour. In addition, 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 compound of Formula I or the combination comprising the compound of Formula 1 or the composition comprising the compound of Formula I also exhibit potent strengthening effect in plants. Accordingly, they can be used for mobilizing the defences of the plant against attack by undesirable micro-organisms.
  • 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 micro-organisms, 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. chlorophyl l content, stay-green effects, etc.) and improved photosynthetic efficiency.
  • the compound of Formula I or the combination comprising the compound of Formula I or the composition comprising the compound of Formula I can reduce the mycotoxin content in the harvested material and the foods and feeds prepared therefrom.
  • Mycotoxins include particularly, but not exclusively, the fol lowing: deoxynivalenol (DON), nivalenol, 15-Ac-DON, 3-Ac-DON, T2- and HT2- toxin, fumonisins, zearalenon, moniliformin, fusarin, diaceotoxyscirpenol (DAS), beauve icin, enniatin, fusaroproliferin, fusarenol, ochratoxins, patulin, ergot alkaloids and afiatoxins which can be produced, for example, by the following fungi : Fiisarhim spec, such as F.
  • verticillioides etc. and also by Aspergillus spec, such as A. flaviis, A. parasiticus, A. nomius, A. ochraceus, A. clavatus, A. terreus, A. versicolor, Penicillium spec, such as P. verrucosum, P. viridicatum, P. citrinum, P. expansion, 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. flaviis, A. parasiticus, A. nomius, A. ochraceus, A. clavatus, A. terreus, A. versicolor, Penicillium spec, such as P. verrucosum, P. viridicatum, P. citrinum, P
  • the compound of Formula I or the combination comprising the compound of Formula I or the composition comprising the compound of Formula I can also be used in the protection of materials, for protection of industrial materials against attack and destruction by phytopathogenic micro-organisms.
  • the compound of Formula I or the combination comprising the compound of Formula I or the composition comprising the compound of 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 micro-organisms.
  • 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 micro-organisms 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 compound of Formula I or the combination comprising the compound of Formula I or the composition comprising the compound of Formula I may prevent adverse effects, such as rotting, decay.; discoloration, decoloration or formation of mould.
  • the compound of Formula I or the compound of Formula I in the composition optionally comprising at least one active compatible compound may also be used against fungal diseases liable to grow on or inside timber.
  • the term "timber" means al l 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 compound of Formula I or the combination comprising the compound of Formula I or the composition comprising the compound of 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 compound of Formula 1 or the combination comprising the compound of Formula I or the composition comprising the compound of Formula 1 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 compound of Formula I or the combination comprising the compound of Formula I or the composition comprising the compound of Formula I may prevent adverse effects, such as rotting, decay, discoloration, decoloration or formation of mould.
  • Micro-organisms capable of degrading or altering the industrial materials include, for example, bacteria, fungi, yeasts, algae and slime organisms.
  • the compound of Formula I or the combination comprising the compound of Formula I or the composition comprising the compound of Formula I preferably act against fungi, especially moulds, wood-discoloring and wood-destroying fungi (Ascomycetes, Basidiomycetes, Deuteromycetes and Zygomycetes), and against slime organisms and algae.
  • micro-organisms 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 glaiicum; Polyporus, such as Polyporus versicolor; Aureobasidium, such as Aureobasidium pulhilans; Sclerophoma, such as Sclerophoma pityophila; Trichoderma, such as Trichoderma viride; Ophiostoma spp., Ceratocystis spp., Humicola spp., Petriella spp., Trichurus spp., Coriolus spp., Gloeophylhim spp., Pleurotus spp.
  • the compound of Formula I or the combination comprising the compound of Formula I or the composition comprising the compound of Formula I 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 compound of Formula I or the combination comprising the compound of Formula I or the composition comprising the compound of Formula I can therefore be used both in medical and in non- medical appl ications.
  • the compound of Formula I or the combination comprising the compound of Formula I or the composition comprising the compound of 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 (GMOs), e.g. plants or seeds.
  • GMOs genetically modified organisms
  • Genetically modified plants (or transgenic plants) are plants of which a heterologous gene has been stably integrated into genome.
  • 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 resistant 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 processability 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 (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 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 which may also be treated according to the invention are plants, such as tobacco plants, with altered post-translational protein modification patterns.
  • the compounds of Formula 3 and 3A can be prepared by one or more of the following methods and variations as described in Schemes 1 - 13.
  • the definitions of J, G, Z, Q and n in the compounds of Formula 1 -24 below are as defined above in the detailed description unless otherwise noted.
  • the preparation of a compound of Formula 3 or 3a involves coupling of an acid of Formula 1 or la respectively with an amine of Formula 2 (or its acid salt) in the presence of a dehydrative coupling reagent such as dicyclohexylcarbodiimide (DCC) or l -(3-dimethylaminopropyl)-3- ethyicarbodiimide hydrochloride (EDC) O-benzotriazol-l-yl-tetramethy!uronium hexafluoro-phosphate (HBTU) or l -[bis(dimethylamino)methylene]- l H- l ,2,3-triazolo[4,5-b]pyridinium 3-oxid hexafluorophosphate (HATU).
  • DCC dicyclohexylcarbodiimide
  • EDC l -(3-dimethylaminopropyl)-3- ethyicarbodiimide hydrochlor
  • Polymer-supported reagents such as polymer-bound cyclohexylcarbodi imide can also be used as coupling agent.
  • the reaction is typically carried out at 0 to 40 °C in a solvent such as dichloromethane or acetonitrile or N, N-dimethylformamide in the presence of a base such as triethylamine or diisopropylethylamine.
  • the compound of formula 3a can be obtained from the compound of Formula 3 by thiating the compound of Formula 3 using a thiating reagent such as phosphorus pentasulfide or 2, 4-bis (4- mefhoxyphenyl)-l, 3-dithia-2, 4-diphosphetane-2, 4-disulfide (Lawesson's reagent).
  • a thiating reagent such as phosphorus pentasulfide or 2, 4-bis (4- mefhoxyphenyl)-l, 3-dithia-2, 4-diphosphetane-2, 4-disulfide (Lawesson's reagent).
  • R 4 CH 2 COOH wherein R 4 is a heterocycl ic ring linked through nitrogen can be prepared by reacting the corresponding R 4 H compound with a halo acetic acid or ester in the presence of a base; followed by hydrolysis.
  • the amine compound of Formula 2 can be prepared from the protected amine compound of Formula 4 wherein Y i is an amine-protecting group.
  • the compound of Formula 4 is converted into the compound of Formula 2 by a suitable method for removing protecting groups described in the literature (Protective Groups in Organic Synthesis"; Theodora W. Greene, Peter G. M. Wuts; Wiley-Interscience; Third Edition; 1999; 494-653).
  • protecting groups described in the literature (Protective Groups in Organic Synthesis"; Theodora W. Greene, Peter G. M. Wuts; Wiley-Interscience; Third Edition; 1999; 494-653).
  • tert-Butoxycarbonyl and benzyloxycarbonyl protecting groups can be removed in an acidic medium for example by using hydrochloric acid or trifluoroacetic acid.
  • Acetyl protecting groups can be removed under basic conditions for example by using potassium carbonate or cesium carbonate.
  • Benzylic protecting groups can be removed hydrogenolytically by using hydrogen in the presence of a catalyst for example palladium on activated carbon.
  • the compound of Formula 2 is separated from the reaction mixture by one of the customary separation techniques. If necessary, the compounds are purified by recrystallization or chromatography, or can, if desired, also be used in the next step without prior purification. It is also possible to isolate the compound of Formula 2 as a salt, for example as a salt of hydrochloric acid or of trifluoroacetic acid.
  • a compound of Formula 4 wherein J-Q contains amine as one of the substituent involves coupling of an acid of Formula 5 with an amine of J-Q (or its acid salt) in the presence of a dehydrative coupling reagent such as dicyclohexylcarbodiimide (DCC) or 1 -(3-dimefhylaminopropyl)-3- etbylcarbodiimide hydrochloride (EDC) O-benzotriazol-l-yl-tetramethyluronium hexafluoro-phosphate (HBTU) or l -[Bis(dimethylamino)methylene]- l H- l ,2,3-triazolo[4,5-b]pyridinium 3-oxid hexafluorophosphate (HATU).
  • DCC dicyclohexylcarbodiimide
  • EDC EDC
  • HBTU O-benzotriazol-l-yl-tetramethyluronium
  • Polymer-supported reagents such as polymer-bound cyclohexylcarbodiimide can also be used as coupling agent.
  • the reaction is typically carried out at 0 to 40 oC in a solvent such as dichloromethane or acetonitrile or N, N-dimethylformamide in the presence of a base such as triethylamine or diisopropylethylamine.
  • the compound of Formula 5 can be prepared by hydrolyzing a compound of Formula 6 using a base or an acid.
  • Preferred bases for the conversion of the compound of Formula 6 into the compound of Formula 5 are sodium hydroxide, lithium hydroxide, potassium hydroxide and the like.
  • Preferred acids for the conversion of the compound of Formula 6 into the compound of Formula 5 are hydrochloride acid, sulfuric acid, acetic acid, trifluroroacetic acid and the like.
  • Preferred solvents for the hydrolysis reactions are water or ethanol or tetrahydrofuran.
  • a compound of Formula 6b can be prepared by a compound of Formula 7 with a compound of Formula 8 in the presence of a base.
  • Suitable bases for such reaction include sodium hydride or potassium carbonate and the reaction is carried out in a solvent such as N, N-dimethylformamide or acetonitrile at 0 to 80 °C.
  • Suitable leaving group Y 2 in the compound of Formula 8 include bromide, iodide, mesylate, triflate and the like, and the compound of Formula 8 can be prepared from the corresponding compounds wherein Y 2 is hydroxy, using general methods known in the art.
  • the compound of Formula J-Q can be prepared by reacting a compound of Formula 9 with ammonium carbamate in the presence of PhI(OAc) 2 in methanol.
  • Different solvents such as acetonitrile, toluene, tetrahydrofuran can also be used for the preparation of the compound of Formula J-Q conversion.
  • Ammonium acetate and ammonia in methanol solution is also suitable as a nitrogen-source for this kind of conversion.
  • a suitably substituted compound of Formula 11 was purchased commercially or can be prepared from the corresponding chloro derivatives using known methods in the literature. Suitable reagents for this conversion can be sulfuric acid or hydrochloric acid or sodium hydroxide. Please refer PCT Patent Application Publication WO2007/39563 WO2014/71044 Lavecchia; Berteina-Raboin; crizt, and Tetrahedron Letters, 2004, 45, 35, 6633-6636.
  • the compound of Formula 11 can be further functionalized using known methods in the literature like chlorination, bromination, trifluromethylation to obtain appropriately substituted heterocyclic ring like pyridone (refer Formula 12).
  • a substituted heterocyclic ring containing a pyridone-l ike moiety can be acylated by reacting with an alkyl ester containing a suitable leaving group such as halogen or mesylate or tosylate in the presence of a base such as potassium carbonate or cesium carbonate in a polar solvent such as N, N-dimethylformamide or NMP with or without heating to obtain the compound of Formula 13.
  • a base such as potassium carbonate or cesium carbonate
  • a polar solvent such as N, N-dimethylformamide or NMP
  • mixtures of O- and N- alkylated products are obtained and the two regio-isomeric products can be separated by means of silica gel or reverse phase chromatography.
  • the addition of l ithium salts, for example lithium chloride to the reaction mixture can be employed to favor N-alkylation over O-alkylation.
  • the obtained aikyl ester can be further hydrolyzed to the corresponding acids by heating or stirring at room temperature in the presence of lithium hydroxide or sodi um hydroxide in solvents like ethanol or water to obtain the novel compound with Formula l a.
  • the preparation of a compound of Formula 15 can be achieved by reacting substituted acetoacetic ester with alkyl hydrazine of Formula 14 with excellent regioselectivity.
  • the compound of Formula 15 can then be selectively alkylated using alkyl halides with or without base to obtain a compound of Formula 16.
  • the compound of Formula 16 can be further functionalized using known methods in the literature like chlorination or bromination or trifluromethylation to obtain appropriately substituted compound of Formula 17.
  • the comound of Formula 17 can be further hydrolyzed by heating or stirring at room temperature in the presence of lithium hydroxide or sodium hydroxide or potassium hydroxide in solvents like ethanol or water to obtain the novel compound of Formula lb.
  • the compound of Formula lb can be used with or without converting it into corresponding acyl chloride.
  • a compound of Formula 18 and hydrazines are commercially available or can be prepared by methods known in the literature.
  • the comound of Formula 18 is reacted with hydrazines to form intermediate of Formula 19.
  • a compound of Formula 19a wherein R 1 is halogen can be prepared from the compound of Formula 19 (R 1 is H) by halogenating it with a halogenating reagent as shown in Scheme 1 1.
  • halogenating reagents known in the literature are suitable for this method including, for example, N- halosuccinimides (e.g., NBS, NCS, NIS), elemental halogen (e.g., Cl 2 , Br 2 , I 2 ), phosphorus oxyhalides, phosphorus trihalides, phosphorus pentahalides, thionyl chloride, sulfuryl chloride, bis(pyridine)iodonium(]) tetrafJuoroborate, tetramethylammonium iodide chloride, tetrafluoroborate and sulfur tetrafluoride.
  • N-halosuccinimides are particularly more suitable for such halogenation reactions.
  • the reaction is carried out in a suitable solvent such as N, N-dimethylformamide, carbon tetrachloride, acetonitrile, dichloromethane, acetic acid, chloroform, benzene, xylenes, chlorobenzene, tetrahydrofuran, 1 , 4 dioxane or the like.
  • a suitable solvent such as N, N-dimethylformamide, carbon tetrachloride, acetonitrile, dichloromethane, acetic acid, chloroform, benzene, xylenes, chlorobenzene, tetrahydrofuran, 1 , 4 dioxane or the like.
  • an organic base such as triethylamine, pyridine, N, N-dimethylaniline or the like can be added.
  • Catalyst such as N, N-dimethylforrnamide or 2, 2'-azobis (2- methylpropionitrile) (AIBN)
  • reaction temperatures range from about room temperature (e.g., 25 °C) to 1 50 °C.
  • room temperature e.g. 25 °C
  • Compounds of Formula 20 and 20a respectively can be prepared by treating the compounds of Formula 19 and 19a with ethyl bromo acetate preferably with bases as shown in the Scheme 1 1 .
  • the reaction is carried out in a suitable solvent such as N, N-dimethylformamide, carbon tetrachloride, acetonitrile, dichloromethane, tetrahydrofuran, acetone, 1 , 4 dioxane or the like.
  • a suitable solvent such as N, N-dimethylformamide, carbon tetrachloride, acetonitrile, dichloromethane, tetrahydrofuran, acetone, 1 , 4 dioxane or the like.
  • an organic base such as triethylamine, pyridine, or inorganic bases such as potassium carbonate, cesium carbonate, sodum carbonate or the like can be used.
  • the compounds of Formula 20 and 20a can be hydrolyzed by treating it with sodium hydroxide or lithium hydroxide or potassium hydroxide to obtain a compound of Formula lc as shown in the Scheme 1 1 .
  • Preferred solvents for the hydrolysis are water or ethanol or tetrahydrofuran.
  • a compound of Formula 12 and hydrazines (R 2 NHNH 2 ) are commercially available or can be prepared by methods known in the literature.
  • the preparation of a compound Formula 21 can be carried out using dimethyl sulphate in the presence of bases like potassium carbonate, cesium carbonate, sodium carbonate or the like as explained in Journal of Heterocyclic Chemistry, 1993, 30, 1 , 49-54.
  • the compound of Formula 21 can be reacted with hydrazine (R 2 NHNH 2 ) in protic solvents like ethanol or methanol to obtain a compound of Formula 22a.
  • a compound of Formula 22b wherein R 1 is halogen can be prepared from the compound of Formula 22a (R 1 is H) by halogenating it with a halogenating reagent as shown in Scheme 1 1.
  • a halogenating reagent known in the literature are suitable for this method including, for example, N- halosuccinimides (e.g., NBS, NCS, NIS), elemental halogen (e.g., Cl 2 , Br 2 , 1 2 ), phosphorus oxyhalides, phosphorus trihalides, phosphorus pentahalides, thionyl chloride, sulfuryl chloride, bis(pyridine)iodonium(I) tetrafluoroborate, tetramethylammonium iodide chloride, tetrafluoroborate and sulfur tetrafluoride.
  • N- halosuccinimides e.g., NBS, NCS, NIS
  • elemental halogen e.g., Cl
  • N-halosuccinimides are particularly more suitable for such halogenation reactions.
  • the reaction is carried out in a suitable solvent such as N, N-dimethylformamide, carbon tetrachloride, acetonitrile, dichloromethane, acetic acid, chloroform, benzene, xylenes, chlorobenzene, tetrahydrofuran, 1 , 4 dioxane or the like.
  • a suitable solvent such as N, N-dimethylformamide, carbon tetrachloride, acetonitrile, dichloromethane, acetic acid, chloroform, benzene, xylenes, chlorobenzene, tetrahydrofuran, 1 , 4 dioxane or the like.
  • an organic base such as triethylamine, pyridine, N, N-dimethylaniline or the like can be added.
  • Catalyst such as N, N-dimethylforrnamide or 2, 2'-azobis (2- methylpropionitrile) (AIBN) can also be used to catalyze such reaction.
  • reaction temperatures range from about room temperature (e.g., 25 °C) to 1 50 °C.
  • room temperature e.g. 25 °C
  • Compounds of Formula 23a and 23b can be prepared by treating the compounds of Formula 22a and 22b, with ethyl bromo acetate preferably with bases as shown in the Scheme 12.
  • the reaction is carried out in a suitable solvent such as N, N-dimethylformamide, carbon tetrachloride, acetonitrile, dichloromethane, tetrahydrofuran, acetone, 1 , 4 dioxane or the like.
  • a suitable solvent such as N, N-dimethylformamide, carbon tetrachloride, acetonitrile, dichloromethane, tetrahydrofuran, acetone, 1 , 4 dioxane or the like.
  • an organic base such as triethylamine, pyridine, or inorganic bases such as potassium carbonate, cesium carbonate, sodum carbonate or the l ike can be used.
  • Compounds of Formula 23a and 23b can be hydrolyzed by treating it with sodium hydroxide or lithium hydroxide or potassium hydroxide to obtain a compound of Formula la as shown in the scheme 12.
  • Preferred solvents for the hydrolysis are water or ethanol or tetrahydrofuran.
  • Substituted compounds of Formula 1 1 can be further functionalized using known methods in the literature like chlorination, Bromination, Trifluromethylation to get appropriately substituted heterocyclic ring like Pyridone (Formula 1 2)
  • References for the said transformations are Zhang, Pei-Zhi et al Tetrahedron, 2016,72(23), 3250-3255; Canibano; Rodriguez; Santos; Sanz-Tejedor; Carreno; Gonzalez; Garcia-Ruano Synthesis, 2001, 14,21 75 - 21 79, PCT Patent Application Publication WO2004/50637.
  • a substituted functional ized heterocyclic ring containing a pyridone-like moiety can be alkylated by reaction with an alkyl ester containing a suitable leaving group such as halogen, mesylate or tosylate, in the presence of a base such as Ag 2 C0 3 or Cs 2 C0 3 , in a polar sol!vent such as N, N-dimethylformamide or NMP, or non-polar solvent such as toluene, xylene with or without heating.to get the compound of Formula 24.
  • a polar sol!vent such as N, N-dimethylformamide or NMP, or non-polar solvent such as toluene, xylene with or without heating.
  • the addition of lithium salts, for example LiCl, to the reaction mixture can be employed to favor N- vs. O- alkylation.
  • the obtained alkyl ester can be further hydrolyzed to the corresponding acids by heating or stirring at room temperature in the presence of Lithium hydroxide or sodium hydroxide in solvents l ike ethanol, water to get the novel compounds with formula 1 .
  • synthesis of a compound of Formula 25 involves simple one-pot aromatic ethyl ester reduction into the corresponding alcohol using NaBH 4 -MeOH system.
  • the aromatic alcohols were obtained by the method explained in the ARKIVOC, 2006, 128- 133, involving the reduction of aromatic ethyl esters in 1 5-60 minutes after refluxing in THF.
  • the respective alcohol products were isolated after aqueous workup in good yield.
  • a compound of Formula 26 can be prepared by bromination of the compound of Formula 25 using CBr /PPh .
  • PBr 3 can also be used as brominating agent.
  • a compound of Formula 27 can be synthesised by treating the compound of Formula 26, with sulfoximine (J-Q) in the presence of a base like K'Obu, NaH, and K 2 C0 3 in solvents like DMF and DMSO.
  • J-Q sulfoximine
  • Synthesis of a compound of Formula 28 can be achieved by treating the compound of Formula 5 and suitable J-Q in presence of triethylamine and diphenylphosphoryl azide (DPPA) as a source of azide in solvents like toluene.
  • DPPA diphenylphosphoryl azide
  • Step A Preparation of ethyl 2-bromo-l,3-thiazole-4-carboxylate
  • Step B Preparation of ethyl 2-(l-(tert-butoxycarbonyl)-l,2,3,6-tetrahydropyridin-4-yl)thiazole-4- carboxylate
  • the reaction mixture was heated to 85 °C for 12 h.
  • the reaction mixture was cooled to 25 °C, filtered through celite bed and washed with methanol.
  • the filtrate was concentrated under reduced pressure and the residue obtained after concentration was purified by column chromatography using 45% ethyl acetate in hexane as an eluent to obtain ethyl 2-( 1 -(tert-butoxycarbonyl)- l ,2,3,6-tetrahydropyridin-4-yl)thiazole-4-carboxylate (50 g, 55% yield).
  • Step C Preparation of ethyl 2-(l-(tert-butoxycarbonyl)piperidin-4-yl)thiazole-4-carboxylate
  • Step D Preparation of 2-(l-(tert-butoxycarbonyl)piperidin-4-yl)thiazole-4-carboxylic acid
  • Step E Preparation of tert-butyl 4-(4-(((2,6-difluorophenyl)(methyl)(oxo)- ⁇ 6 - sulfanylidene)carbamoyI)thiazol-2-yl)piperidine-l-carboxylate
  • Step F Preparation of N-((2,6-difluorophenyI)(methyl)(oxo) ⁇ 6 -sulfanylidene)-2-(piperidin-4-yI) thiazole-4-carboxamide
  • Step G Preparation of N-((2,6-difluorophenyl)(methyI)(o o)- ⁇ 6 -sulfanylidene)-2-(l-(2-(5-methyl-3- (trifluoromethyl)-lH-pyrazol-l-yI)acetyl)piperidin-4-y])thiazole-4-carboxamide (Compound 15)
  • 2-(5-methyl-3-(trifluoromethyl)-l H-pyrazol- l -yl)acetic acid 129 mg, 0.6 mmol
  • N, N-dimethy!formamide 5 mL
  • l -[bis(dimethylamino)methylene]- l H-l ,2,3-triazolo[4,5-b]pyridinium 3- oxid hexafluorophosphate HATU
  • N-((3-bromophenyl)(methyl)(oxo) ⁇ 6 -sulfanylidene)-2-(pipendin-4-yl)thiazole-4- carboxamide 0.3 g, 0.6 mmol
  • N, N-dimethylformamide 8 mL
  • N, N-di isopropylethylamine 0.5 mL, 3.0 mmol
  • N-((2,6-dimethylphenyl)(ethyl)(oxo) ⁇ 6 -sulfanylidene)-2-(piperidin-4-yl)thiazole-4- carboxamide 0.3 g, 0.6 mmol
  • N, N-dimethylformamide 4 mL
  • N, N-diisopropylethylamine 6 mL, 3.2 mmol
  • Step B Preparation of (2,6-difluorophenyl)(imino)(methyl)-X 6 -siiIfanone
  • Step A Preparation of (2,6-dimethyIphenyI)(ethyl)sulfane
  • 2,6-dimethylbenzenethiol 1 .0 g, 7.2 mmol
  • triethylamine 1 .0 mL, 7.2 mmol
  • 2,6-dimethylbenzenethiol 1 .0 g, 7.2 mmol
  • Step B Preparation of (2,6-dimethylphenyl)(ethyl)(imino)- 6 -suIfanone
  • Step A Preparation of tert-butyl 4-(4-(bromomethyl)thiazol-2-yl)piperidine-l-carboxyIate
  • Step B Preparation of tert-butyl 4-(4-((((3-bromophenyl)(methy])(oxo)- 6 - sulfaneylidene)amino)methyl)thiazol-2-yl)piperidine-l-carboxyIate
  • tert-butyl 4-(4-(bromomethyl)thiazol-2-yl)piperidine- l -carboxylate (0.71 g, 2 mmol)
  • 3- bromophenyl)(imino)(methyl)- 6 -sulfanone (0.47g, 2 mmol) in dimethylformamide (20 mL) at 0 °C
  • potassium tert-butoxide (0.34 g, 3 mmol
  • the resulting reaction mixture was stirred at 0 °C for 2 h.
  • the reaction mixture was quenched with ice ( 10 g) and poured into a mixture of ethyl acetate (200 mL) and water ( 1 50 mL). Ethyl acetate and water layers were separated and the aqueous layer was extracted thrice with ethyl acetate (200 mL). The combined ethyl acetate layer was dried over anhydrous sodium sulphate, filtered, and concentrated.
  • Step C Preparation of (3-bromophenyl)(methyl)(((2-(piperidin-4-yl)thiazol-4-yl)methyl)imino)- 6 - sulfanone
  • Step E Preparation of (3-bromophenyJ)(met yl)(((2-(l-(2-(5-methyl-3-(trifluoromethyl)-lH- pyrazol-l-yl)acetyl)piperidin-4-yl)thiazol-4-yI)methyl)imino)-X 6 -sulfanone
  • Step A Preparation of tert-butyl 4-(4-(3-((4-bromophenyl) (methyl) (oxo)- 6 -sulfanylidene) ureido) thiazol-2-yl) piperidine-l-carboxylate
  • tert-butyl 4-(4-(azidocarbonyl) thiazol-2-yl) piperidine-l -carboxylate was dried over anhydrous sodium sulphate and concentrated to obtain tert-butyl 4-(4-(azidocarbonyl) thiazol-2-yl) piperidine-l -carboxylate.
  • tert-butyl 4-(4-(azidocarbonyl)thiazol-2-yl)piperidine- l -carboxylate and (4- bromophenyl)(imino)(methyl) ⁇ 6 -sulfanone were taken up in acetonitrile (20 mL) and heated to 90 °C for 1 6 h.
  • Step B Preparation of l-((4-bromophenyl) (methyl) (oxo) ⁇ 6 -sulfanylidene)-3-(2-(piperidin-4-yl) thiazol-4-yl) urea 2, 2, 2-trifluoroacetate
  • a solution of tert-butyl 4-(4-(3-((4-bromophenyl) (methyl) (oxo)- 6 -sulfanylidene) ureido) thiazol-2- yl) piperidine- l -carboxylate ( 1 g, 1.8 mmol) in dichloromethane ( 10 mL), was added trifluoroacetic acid (4.2 mL, 55 mmol).
  • Step C l-(2-(l -(2-(3, 5-bis (difluoromethyl)-lH-pyrazol-l-yl) acetyl) piperidin-4-yl) thiazoI-4-yl)-3- ((4-bromophenyl) (methyl) (oxo)- '-sulfanylidene) urea
  • the resulting reaction mixture was stirred at 25 °C for 2 h.
  • the reaction mixture was diluted with cold water (50 mL) and extracted twice with ethyl acetate (50 mL).
  • the ethyl acetate layer was washed twice with cold water (50 mL), dried over anhydrous sodium sulphate and 5 concentrated under reduced pressure.
  • the product was purified by column chromatography using 100% ethyl acetate as an eluent to obtain l-(2-(l-(2-(3,5-bis(difluoromethyl)-lH-pyrazol-l-yl)acetyl)piperidin- 4-yl)thiazol-4-yl)-3-((4-bi mophenyl)(methyl)(oxo)- 6 -sulfanylidene)urea (200 mg, 0.3 mmol, 45% yield).
  • GREENHOUSE Compounds were dissolved in 2% DMSO/Acetone & then mixed with water to calibrated spray volume of 50 mL. This 50 mL spray solution was poured into the spray bottles for further applications.
  • healthy young Tomato plants raised in the greenhouse were sprayed with active compound preparation at the stated application rates inside the spray cabinets using hallow-cone nozzles.
  • the plants were inoculated with sporangial suspension (Cold sterile water) containing 0.24x 1 0 6 Phytophthora infestans inoculum.
  • Example B Plasmopara viticola test in Grape

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Abstract

La présente invention concerne un composé sélectionné dans la formule I et ses sels, complexes métalliques, N-oxydes, isomères et polymorphes : dans la formule E, Z, R3, n, G, J et Q ont la signification telle que définie dans la description.
PCT/IB2018/056580 2017-09-08 2018-08-29 Nouveaux composés hétérocycliques fongicides WO2019048988A1 (fr)

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WO2021094904A2 (fr) 2019-11-11 2021-05-20 Pi Industries Ltd. Nouvelles sulfilimines ou sulfoximines contenant des composés hétérocycliques fongicides
WO2021094903A1 (fr) 2019-11-11 2021-05-20 Pi Industries Ltd. Dérivés 1-(4-(4-(5-phényl-4,5-dihydroisoxazol-3-yl)thiazol-2-yl)pipéridin-1-yl)-éthan-1-one et composés apparentés utiles en tant que fongicides pour la protection des cultures
WO2021094905A1 (fr) 2019-11-11 2021-05-20 Pi Industries Ltd. Dérivés 1-(4-(4-(5-phényl-4,5-dihydroisoxazol-3-yl)thiazol-2-yl)pipéridine-1-yl)-éthane-1-one et composés associés servant de fongicides pour la protection des récoltes
WO2022130188A1 (fr) 2020-12-15 2022-06-23 Pi Industries Ltd. Composition agrochimique comprenant des composés de pipéridine thiazole
WO2022243810A1 (fr) 2021-05-15 2022-11-24 Pi Industries Ltd. Nouvelle composition agrochimique comprenant des composés de pipéridine thiazole
WO2023007426A1 (fr) 2021-07-29 2023-02-02 Pi Industries Ltd. Nouveaux composés styréniques et leur procédé de préparation

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CN114158670A (zh) * 2021-12-03 2022-03-11 西华大学 一种利用二氧化氯水溶液及丁香精油联合处理抑制粮食中禾谷镰刀菌的方法

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WO2021094904A2 (fr) 2019-11-11 2021-05-20 Pi Industries Ltd. Nouvelles sulfilimines ou sulfoximines contenant des composés hétérocycliques fongicides
WO2021094903A1 (fr) 2019-11-11 2021-05-20 Pi Industries Ltd. Dérivés 1-(4-(4-(5-phényl-4,5-dihydroisoxazol-3-yl)thiazol-2-yl)pipéridin-1-yl)-éthan-1-one et composés apparentés utiles en tant que fongicides pour la protection des cultures
WO2021094905A1 (fr) 2019-11-11 2021-05-20 Pi Industries Ltd. Dérivés 1-(4-(4-(5-phényl-4,5-dihydroisoxazol-3-yl)thiazol-2-yl)pipéridine-1-yl)-éthane-1-one et composés associés servant de fongicides pour la protection des récoltes
WO2021094904A3 (fr) * 2019-11-11 2021-06-24 Pi Industries Ltd. Nouvelles sulfilimines ou sulfoximines contenant des composés hétérocycliques fongicides
CN114761403A (zh) * 2019-11-11 2022-07-15 Pi工业有限公司 用作作物保护杀菌剂的1-(4-(4-(5-苯基-4,5-二氢异噁唑-3-基)噻唑-2-基)哌啶-1-基)-乙烷-1-酮衍生物及相关化合物
CN115052875A (zh) * 2019-11-11 2022-09-13 Pi工业有限公司 作为作物保护用杀真菌剂的4-(4-(4,5-二氢异恶唑-3-基)噻唑-2-基)哌啶硫亚胺或亚砜亚胺衍生物及相关化合物
WO2022130188A1 (fr) 2020-12-15 2022-06-23 Pi Industries Ltd. Composition agrochimique comprenant des composés de pipéridine thiazole
WO2022243810A1 (fr) 2021-05-15 2022-11-24 Pi Industries Ltd. Nouvelle composition agrochimique comprenant des composés de pipéridine thiazole
WO2023007426A1 (fr) 2021-07-29 2023-02-02 Pi Industries Ltd. Nouveaux composés styréniques et leur procédé de préparation

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