WO1999028305A1 - Amides cycliques fongicides - Google Patents

Amides cycliques fongicides Download PDF

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Publication number
WO1999028305A1
WO1999028305A1 PCT/US1998/024265 US9824265W WO9928305A1 WO 1999028305 A1 WO1999028305 A1 WO 1999028305A1 US 9824265 W US9824265 W US 9824265W WO 9928305 A1 WO9928305 A1 WO 9928305A1
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Prior art keywords
phenyl
formula
optionally substituted
compounds
alkyl
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PCT/US1998/024265
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English (en)
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Michael Paul Walker
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E.I. Du Pont De Nemours And Company
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Priority to AU14078/99A priority Critical patent/AU1407899A/en
Publication of WO1999028305A1 publication Critical patent/WO1999028305A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D249/12—Oxygen or sulfur atoms
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/44—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a nitrogen atom attached to the same carbon skeleton by a single or double bond, this nitrogen atom not being a member of a derivative or of a thio analogue of a carboxylic group, e.g. amino-carboxylic acids
    • A01N37/50—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a nitrogen atom attached to the same carbon skeleton by a single or double bond, this nitrogen atom not being a member of a derivative or of a thio analogue of a carboxylic group, e.g. amino-carboxylic acids the nitrogen atom being doubly bound to the carbon skeleton
    • 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
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered 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
    • A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
    • A01N43/647—Triazoles; Hydrogenated triazoles
    • A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/82—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with three ring hetero atoms
    • 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
    • A01N55/00—Biocides, pest repellants or attractants, or plant growth regulators, containing organic compounds containing elements other than carbon, hydrogen, halogen, oxygen, nitrogen and sulfur
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
    • C07C251/32—Oximes
    • C07C251/50—Oximes having oxygen atoms of oxyimino groups bound to carbon atoms of substituted hydrocarbon radicals
    • C07C251/60—Oximes having oxygen atoms of oxyimino groups bound to carbon atoms of substituted hydrocarbon radicals of hydrocarbon radicals substituted by carboxyl groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
    • 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
    • C07D417/02—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 two hetero rings
    • C07D417/12—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 two hetero rings linked by a chain containing hetero atoms as chain links

Definitions

  • This invention relates to certain fungicidal cyclic amides, their N-oxides, agriculturally suitable salts and compositions, and methods of their use as fungicides and arthropodicides.
  • the control of plant diseases caused by fungal plant pathogens is extremely important in achieving high crop efficiency. Plant disease damage to ornamental, vegetable, field, cereal, and fruit crops can cause significant reduction in productivity and thereby result in increased costs to the consumers.
  • the control of arthropod pests is also extremely important in achieving high crop efficiency. Arthropod damage to growing and stored agronomic crops can cause significant reduction in productivity and thereby result in increased costs to the consumer.
  • the control of arthropod pests in forestry, greenhouse crops, ornamentals, nursery crops, stored food and fiber products, livestock, household, and public and animal health is also important. Many products are commercially available for these purposes, but the need continues for new compounds which are more effective, less costly, less toxic, environmentally safer or have different modes of action.
  • This invention is directed to compounds of Formula I including all geometric and stereoisomers, N-oxides, and agriculturally suitable salts thereof, agricultural compositions containing them and their use as fungicides and arthropodicides:
  • X is OR 1 , SCO ⁇ R 1 or halogen;
  • A is O, S, N, NR 5 or CR 7 ;
  • G is C or N; provided that when G is C, A is O, S or NR 5 and the floating double bond is attached to G; and when G is N, A is N or CR 7 and the floating double bond is attached to A;
  • W is O or S
  • YZ is a group consisting of (a) 3 or more atoms independently selected from the group C, N, O, S, Si and Ge, provided that at least 2 of said atoms are C, and (b) additional atoms selected from H, F, CI, Br and I;
  • R 1 is C r C 6 alkyl, C r C 6 haloalkyl, C 2 -C 6 alkenyl, C 2 -C 6 haloalkenyl, C 2 -C 6 alkynyl,
  • R 2 , R 5 and R 6 are each independently selected from the group H, Cj-C 6 alkyl, C j -C 6 haloalkyl, C 2 -Cg alkenyl, C 2 -Cg haloalkenyl, C -C6 alkynyl, C -Cg haloalkynyl, C3-C 6 cycloalkyl, C 2 -C4 alkylcarbonyl and C -C alkoxycarbonyl;
  • R 3 is halogen, CF 3 , C 1 -C3 alkyl or C1-C3 alkoxy;
  • R 4 is H, halogen, CF 3 , C r C 3 alkyl or C r C 3 alkoxy;
  • R 7 is H, halogen or methyl; m is 0, 1 or 2; and s is 0 or 1 ; provided that
  • This invention also provides compounds of Formula II including all geometric and stereoisomers and their use as intermediates for the preparation of the fungicides and arthropodicides of Formula I wherein wherein T is
  • X is OR 1 , SCO ⁇ R 1 or halogen; A is O, S, N, NR 5 or CR 7 ; G is C or N; provided that when G is C, A is O, S or NR 5 and the floating double bond is attached to G; and when G is N, A is N or CR 7 and the floating double bond is attached to A; W is O or S; Y 1 is OH, SH, OSO 2 CH 3 , OSO 2 (4-CH 3 -Ph), CHO, CH(R ⁇ )OH, CHCR ⁇ Cl,
  • R 1 is C r C 6 alkyl, C r C 6 haloalkyl, C 2 -C 6 alkenyl, C 2 -C 6 haloalkenyl, C 2 -C 6 alkynyl,
  • R 2 , R 5 and R 6 are each independently selected from the group H, C j -Cg alkyl, C C 6 haloalkyl, C 2 -C6 alkenyl, C 2 - haloalkenyl, C 2 -C6 alkynyl, C -Cg haloalkynyl,
  • R 3 is halogen, CF 3 , C1-C3 alkyl or C j -C3 alkoxy
  • R 4 is H, halogen, CF 3 , C r C 3 alkyl or C r C 3 alkoxy
  • R 7 is H, halogen or methyl
  • R 11 is H, C 1 -C alkyl or cyclopropyl
  • m is 0, 1 or 2
  • s is 0 or 1 ; provided that when A is N, G is N, X is S(O) m R 1 and m is 0, then Y 1 is other than haloalkyl.
  • alkyl used in the compound words, such as,
  • alkylthio includes straight-chain or branched alkyl, such as, methyl, ethyl, /z-propyl, z ' -propyl, or the different butyl, pentyl or hexyl isomers.
  • alkyl used alone or in the compound word “haloalkyl” includes straight-chain or branched alkyl, such as, methyl, ethyl, w-propyl, z ' -propyl, or the different butyl, pentyl, hexyl, heptyl, octyl, nonyl and decyl isomers.
  • Alkenyl includes straight-chain or branched alkenes such as vinyl, 1-propenyl, 2-propenyl and the different butenyl, pentenyl and hexenyl isomers.
  • Alkenyl also includes polyenes such as 1 ,2-propadienyl and 2,4-hexadienyl.
  • Alkynyl includes straight-chain or branched alkynes such as ethynyl, 1-propynyl, 2-propynyl and the different butynyl, pentynyl and hexynyl isomers.
  • Alkynyl can also include moieties comprised of multiple triple bonds such as 2,5-hexadiynyl.
  • Alkoxy includes, for example, methoxy, ethoxy, «-propyloxy, isopropyloxy and the different butoxy, pentoxy and hexyloxy isomers.
  • Alkylthio includes branched or straight-chain alkylthio moieties such as methylthio, ethylthio, and the different propylthio, butylthio, pentylthio and hexylthio isomers.
  • Alkylsulfinyl includes both enantiomers of an alkylsulfinyl group.
  • alkylsulfinyl examples include CH 3 S(O), CH 3 CH 2 S(O), CH 3 CH 2 CH 2 S(O), (CH 3 ) 2 CHS(O) and the different butylsulfinyl, pentylsulfinyl and hexylsulfinyl isomers.
  • alkylsulfonyl examples include CH 3 S(O) 2 , CH 3 CH 2 S(O)2, CH 3 CH2CH 2 S(O) 2 , (CH 3 ) 2 CHS(O) 2 and the different butylsulfonyl, pentylsulfonyl and hexylsulfonyl isomers.
  • Cycloalkyl includes, for example, cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl.
  • 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. Examples of “haloalkyl” include F 3 C, C1CH 2 , CF 3 CH 2 and CF 3 CC1 2 .
  • haloalkenyl “haloalkynyl”, “haloalkoxy”, “haloalkylthio”, and the like, are defined analogously to the term “haloalkyl”.
  • haloalkynyl examples include HC ⁇ CCHCl, CF 3 C ⁇ C, CCI3C--.C and FCH 2 C ⁇ CCH 2 .
  • haloalkoxy examples include CF 3 O, CCl 3 CH 2 O, HCF 2 CH 2 CH 2 O and CF 3 CH 2 O.
  • haloalkylthio examples include CC1 3 S, CF 3 S, CC1 3 CH 2 S and C1CH 2 CH 2 CH 2 S.
  • Z examples include C ⁇ -C 10 alkyl; C 3 -C 8 cycloalkyl; phenyl; naphthalenyl; anthracenyl; phenanthrenyl; lH-pyrrolyl; furanyl; thienyl; lH-pyrazolyl; lH-imidazolyl; isoxazolyl; oxazolyl; isothiazolyl; thiazolyl; lH-l,2,3-triazolyl; 2H-l,2,3-triazolyl; lH-l,2,4-triazolyl; 4H-l,2,4-triazolyl; 1,2,3-oxadiazolyl; 1,2,4-oxadiazolyl;
  • Cj-C The total number of carbon atoms in a substituent group is indicated by the "Cj-C,” prefix where i and j are numbers from 1 to 10.
  • C1-C3 alkylsulfonyl designates methylsulfonyl through propylsulfonyl.
  • a group contains a substituent which can be hydrogen, for example R 2 or R 7 , then, when this substituent is taken as hydrogen, it is recognized that this is equivalent to said group being unsubstituted.
  • a group is optionally substituted with a substituent, for example with R 10 , then, when the group is not substituted with that substituent, it is recognized that this is equivalent to said group having a hydrogen substituent.
  • Compounds of this invention can exist as one or more stereoisomers.
  • the various stereoisomers include enantiomers, diastereomers, atropisomers and geometric isomers.
  • one stereoisomer may be more active and/or may exhibit beneficial effects when enriched relative to the other stereoisomer(s) or when separated from the other stereoisomer(s).
  • R 3 is other than fluorine
  • R 4 is other than hydrogen and fluorine.
  • the present invention comprises compounds selected from Formula I and agriculturally suitable salts thereof.
  • the compounds of the invention may be present as a mixture of stereoisomers, individual stereoisomers, or as an optically active form.
  • the salts of the compounds of the invention include acid-addition salts with inorganic or organic acids such as hydrobromic, hydrochloric, nitric, phosphoric, sulfuric, acetic, butyric, fumaric, lactic, maleic, malonic, oxalic, propionic, salicylic, tartaric, 4-toluenesulfonic or valeric acids.
  • inorganic or organic acids such as hydrobromic, hydrochloric, nitric, phosphoric, sulfuric, acetic, butyric, fumaric, lactic, maleic, malonic, oxalic, propionic, salicylic, tartaric, 4-toluenesulfonic or valeric acids.
  • R 4 is hydrogen.
  • Preferred compounds for reasons of better activity and/or ease of synthesis are: Preferred 1.
  • each R 13 is halogen, C r C 6 alkyl, C r C 6 haloalkyl, C r C 6 alkoxy, C r C 6 haloalkoxy, cyano or thiocyanato;
  • R 14 is H, C r C 6 alkyl, C r C 6 haloalkyl, C r C 6 alkoxy, C r C 6 haloalkoxy; and r is 1, 2, 3 or 4.
  • R 3 is methyl
  • Z is phenyl each optionally substituted with R 9 and optionally substituted with one or more R 10 ; or a 5 or 6-membered aromatic heterocyclic ring, each heterocyclic ring containing 1 to 4 heteroatoms independently selected from the group nitrogen, oxygen, and sulfur, provided that each heterocyclic ring contains no more than 3 nitrogens, no more than 1 oxygen, and no more than 1 sulfur, each aromatic heterocyclic ring optionally substituted with R 9 and optionally substituted with one or more R 10 Preferred 3.
  • A is N
  • G is N
  • W is O;
  • X is OR 1 ; R 1 is methyl; and R 2 is methyl.
  • Preferred 4. Compounds of Preferred 1 wherein: T is T 2 ;
  • R 3 is methyl
  • Z is phenyl each optionally substituted with R 9 and optionally substituted with one or more R 10 ; or a 5 or 6-membered aromatic heterocyclic ring, each heterocyclic ring containing 1 to 4 heteroatoms independently selected from the group nitrogen, oxygen, and sulfur, provided that each heterocyclic ring contains no more than 3 nitrogens, no more than 1 oxygen, and no more than 1 sulfur, each aromatic heterocyclic ring optionally substituted with R 9 and optionally substituted with one or more R 10 Preferred 5.
  • T is T 3 ;
  • R 3 is methyl; and Z is phenyl each optionally substituted with R 9 and optionally substituted with one or more R 10 ; or a 5 or 6-membered aromatic heterocyclic ring, each heterocyclic ring containing 1 to 4 heteroatoms independently selected from the group nitrogen, oxygen, and sulfur, provided that each heterocyclic ring contains no more than 3 nitrogens, no more than 1 oxygen, and no more than 1 sulfur, each aromatic heterocyclic ring optionally substituted with R 9 and optionally substituted with one or more R 10 Preferred 6.
  • T is T 4 ;
  • R 3 is methyl; and
  • Z is phenyl each optionally substituted with R 9 and optionally substituted with one or more R 10 ; or a 5 or 6-membered aromatic heterocyclic ring, each heterocyclic ring containing 1 to 4 heteroatoms independently selected from the group nitrogen, oxygen, and sulfur, provided that each heterocyclic ring contains no more than 3 nitrogens, no more than 1 oxygen, and no more than 1 sulfur, each aromatic heterocyclic ring optionally substituted with R 9 and optionally substituted with one or more R 10
  • Most preferred are compounds of Preferred 6 selected from the group: ⁇ -(methoxyimino)-N,2-dimethyl-5-[[[[l-[3-
  • Z is selected from the group 1,2,3,4-tetrahydrohnaphthalenyl; phenyl; naphthalenyl; lH-pyrrolyl; uranyl; thienyl; lH-pyrazolyl; lH-imidazolyl; isoxazolyl; oxazolyl; isothiazolyl; thiazolyl; lH-l,2,3-triazolyl; 2H-l,2,3-triazolyl; lH-l,2,4-triazolyl; 4H-l,2,4-triazolyl; 1,2,3-oxadiazolyl; 1,2,4-oxadiazolyl; 1,2,5-oxadiazolyl; 1,3,4-oxadiazolyl; 1,2,3-thiadiazolyl; 1,2,4-thiadiazolyl; 1,2,5-thiadiazolyl; 1,3,4-thiadiazolyl; pyridinyl;
  • Z is phenyl, thiazolyl, 1,2,4-thiadiazolyl, pyridinyl or pyrimidinyl each optionally substituted with R 9 and optionally substituted with one or more R 10 .
  • This invention also provides compounds of Formula II including all geometric and stereoisomers which are useful as intermediates for the preparation of the fungicides and arthropodicides of Formula I.
  • compounds of Formula II wherein Y 1 is O ⁇ , OSO 2 C ⁇ 3 , CHO, CH 2 OH, CH 2 C1, CH 2 Br, CH 2 I or CH 2 OSO 2 CH 3 .
  • compounds of Formula II wherein T is T 1 compounds of Formula II wherein T is T 2
  • compounds of Formula II wherein T is T 3 or compounds of Formula II wherein T is T 4 are compounds of Formula II wherein T is T 1 , G is N, A is N, X is OR 1 and R 3 is methyl.
  • This invention also relates to fungicidal compositions comprising fungicidally effective amounts of the compounds of the invention and at least one of a surfactant, a solid diluent or a liquid diluent.
  • fungicidal compositions comprising fungicidally effective amounts of the compounds of the invention and at least one of a surfactant, a solid diluent or a liquid diluent.
  • the preferred compositions of the present invention are those which comprise the above preferred compounds.
  • This invention also relates to a method for controlling plant diseases caused by fungal plant pathogens comprising applying to the plant or portion thereof, or to the plant seed or seedling, a fungicidally effective amount of the compounds of the invention (e.g., as a composition described herein).
  • a fungicidally effective amount of the compounds of the invention e.g., as a composition described herein.
  • the preferred methods of use are those involving the above preferred compounds.
  • This invention also relates to arthropodicidal compositions comprising arthropodicidally effective amounts of the compounds of the invention and at least one of a surfactant, a solid diluent or a liquid diluent.
  • the preferred compositions of the present invention are those which comprise the above preferred compounds.
  • This invention also relates to a method for controlling arthropods comprising contacting the arthropods or their environment with an arthropodicidally effective amount of the compounds of the invention (e.g., as a composition described herein). The preferred methods of use are those involving the above preferred compounds. DETAILS OF THE SYNTHESIS
  • the compounds of Formula I can be prepared by one or more of the following methods and variations as described in Schemes 1-44.
  • the definitions of T, A, G, W, X, Y, Y ⁇ Y 8 , Z, R J -R 22 , m, r and s in the compounds of Formulae 1-61 below are as defined above in the Summary of the Invention or in the Schemes hereinafter.
  • Compounds of Formulae la-Ir are various subsets of the compounds of Formula I, and all substituents for Formulae la-Ir are as defined above for Formula I.
  • a compound of Formula I wherein T is T 1 and R 2 is H may exist as tautomer la or lb, or both la and lb.
  • Procedures 1) to 5 describe syntheses involving construction of the heterocycle after the formation of the aryl moiety.
  • Procedure 5) describes syntheses of the aryl moiety with the T-moiety already in place.
  • Suitable solvents are selected from the group consisting of polar aprotic solvents such as acetonitrile, NN-dimethylformamide or dimethyl sulfoxide; ethers such as tetrahydrofuran, dimethoxyethane, or diethyl ether; ketones such as acetone or 2-butanone; hydrocarbons such as toluene or benzene; and halocarbons such as dichloromethane or chloroform.
  • Use of trimethylsilyldiazomethane requires a protic cosolvent such as methanol. For examples of these procedures, see Chem. Pharm. Bull. 1984, 32, 3759.
  • Suitable Lewis acids include trimethylsilyl triflate and tetrafluoroboric acid.
  • the alkyl trichloroacetimidates can be prepared from the appropriate alcohol and trichloroacetonitrile as described in the literature (J. Danklmaier and H. Honig, Synth. Commun. 1990, 20, 203).
  • a trialkyloxonium tetrafluoroborate e.g., Meerwein's salt
  • the use of trialkyloxonium salts as powerful alkylating agents is well known in the art (see U. Schollkopf, U. Groth, C. Deng, Angew. Chem., Int. Ed. Engl. 1981, 20, 798).
  • Appropriate bases include alkali metal alkoxides such as potassium tert-butoxide, inorganic bases such as sodium hydride and potassium carbonate, pyridine, or tertiary amines such as triethylamine, l,8-diazabicyclo[5.4.0]undec-7-ene (DBU), and triethylenediamine.
  • alkali metal alkoxides such as potassium tert-butoxide
  • inorganic bases such as sodium hydride and potassium carbonate
  • pyridine or tertiary amines such as triethylamine, l,8-diazabicyclo[5.4.0]undec-7-ene (DBU), and triethylenediamine.
  • X 1 OH
  • the nucleophiles of Formula 6 are N-substituted hydroxylamines (HO- ⁇ HR 2 ) and substituted hydrazines (H ⁇ (R 5 )- ⁇ HR 2 ). Examples of such nucleophiles are N-methylhydroxylamine and methylhydrazine.
  • CI, 1-i idazolyl Esters of Formula 5a can be prepared from copper (I)-catalyzed reaction of malonate esters with substituted iodobenzenes of Formula 8 according to methods adapted from A. Osuka, T. Kobayashi and H. Suzuki, Synthesis 1983, 67, and illustrated in Scheme 3.
  • Scheme 3
  • R C r C 4 alkyl
  • malonate esters of Formula 5 a can be prepared by treating phenyl acetic acid esters of Formula 9a with a dialkyl carbonate or alkyl chloroformate in the presence of a suitable base such as, but not limited to, sodium metal and sodium hydride
  • Esters of Formula 9a (compounds of Formula 9 wherein E 1 is OR) can be prepared from acid-catalyzed alcoholysis of phenyl acetonitriles of Formula 10 or by esterification of phenyl acetic acids of Formula 11 as illustrated in Scheme 5 (see Org. Synth., Coll. Vol. I 1941; 270).
  • Scheme 5 See Org. Synth., Coll. Vol. I 1941; 270).
  • R C r C 4 alkyl Phenyl acetic acid esters of Formula 9b (compounds of Formula 9a wherein Y is Y 2 ) can also be prepared by copper (I)-catalyzed condensation of phenyl halides of Formula 12 with compounds of Formula 13 as described in EP-A-307,103 and illustrated below in Scheme 6.
  • Compounds of Formula 12 can be prepared by the Arndt-Eistert synthesis starting from benzoic acids of Formula 14 as illustrated in Scheme 7, (see F. Arndt, B. Eistert 1935, Ber. 68, 200; T. Aoyama, T. Shioiri, Tetrahedron Letters 1980, 21, 4461).
  • a halogenating agent such as thionyl chloride
  • an alkylating agent such as diazomethane
  • esters of Formula 9c can also be prepared by forming the Y 3 bridge using conventional nucleophilic substitution chemistry (Scheme 9). Displacement of an appropriate leaving group (Lg) in electrophiles of Formula 17 or 18 with a nucleophilic ester of Formula 16 affords compounds of Formula 9c.
  • a base for example sodium hydride, is used to generate the corresponding alkoxide or thioalkoxide of the compound of Formula 16.
  • R C ⁇ -C4 alkyl
  • Formula 16b (compounds of Formula 16 where R 14 is CH2OH or CH 2 SH) can be prepared by metal-halogen exchange in compounds of Formula 12 followed by quenching with the appropriate electrophile.
  • a suitable alkyllithium such as fl-butyllithium in an inert solvent such as ether or tetrahydrofiiran (THF) followed by quenching with an electrophile such as paraformaldehyde
  • an electrophile such as paraformaldehyde
  • a formaldehyde equivalent D-CHO (where D is (CH 3 ) N, or OMe) followed by reduction of the aldehyde with a suitable reducing agent yields compounds of Formula 16b.
  • reducing agents sodium borohydride (NaBH4), sodium cyanoborohydride (NaCNBH4) and diisobutylaluminum hydride (DIBAL-H) (Scheme 10).
  • Suitable inert solvents are methanol, ethanol, methylene chloride and tetrahydrofiiran, (see M. Hudlicky, Reductions in Organic Chemistry; John Wiley & Sons: New York, 1986).
  • esters of Formula 9d can also be prepared by forming the Y 4 bridge from substituted hydroxylamines 16d and carbonyl compounds 19.
  • the hydroxylamines 16d are in turn prepared from esters 16c.
  • Compounds of Formula 16c where the Lg is Br, CI, I, OSO 2 CH 3 or OSO 2 (4-Me-Ph) can be prepared from compounds of Formula 16b, (see March, J. Advanced Organic Chemistry; 3rd ed., John Wiley: New York, 1985). This method has been described in EP-A-600,835 and is illustrated in Scheme 11.
  • reaction with the sulfonyl halides may be performed in the presence of a suitable base (e.g., triethylamine).
  • a suitable base e.g., triethylamine
  • Suitable oxidizing reagents include /wet ⁇ -chloro-peroxybenzoic acid, hydrogen peroxide and Oxone® (KHSO 5 ).
  • halo-compounds of Formula 20d can be prepared from hydrazides of Formula 22 as illustrated in Scheme 15.
  • the compound of Formula 22 is treated with excess of a thionyl halide such as thionyl chloride.
  • the product formed first is the ring-closed compound of Formula 23 which can be isolated or converted in situ to the compound of Formula 20d; see P. Molina, A. Tarraga, A. Espinosa, Synthesis 1989, 923 for a description of this process.
  • Ketene dithioacetals of Formula 25a (compounds of Formula 25 wherein R 16 is
  • CO2(Cj-C4 alkyl) can be prepared by condensing phenyl acetic acid esters of Formula 9a with carbon disulfide in the presence of a suitable base, followed by reaction with two equivalents of an R ⁇ -halide, such as iodomethane or propargyl bromide (Scheme 18).
  • R C ⁇ -C 4 alkyl 25a
  • the carbonylating agents can be alkyl chloroformates or dialkyl carbonates. Some of these carbonylating reactions may require the addition of a base to effect reaction.
  • Appropriate bases include alkali metal alkoxides such as potassium tert-butoxide, inorganic bases such as sodium hydride and potassium carbonate, pyridine, or tertiary amines such as triethylamine, l,8-diazabicyclo[5.4.0]undec-7-ene (DBU) or triethylenediamine.
  • alkali metal alkoxides such as potassium tert-butoxide
  • inorganic bases such as sodium hydride and potassium carbonate
  • pyridine or tertiary amines
  • tertiary amines such as triethylamine, l,8-diazabicyclo[5.4.0]undec-7-ene (DBU) or triethylenediamine.
  • Suitable solvents include polar aprotic solvents such as acetonitrile, N,N-dimethylformamide, or dimethyl sulfoxide; ethers such as tetrahydrofiiran, dimethoxyethane or diethyl ether; ketones such as acetone or 2-butanone; hydrocarbons such as toluene or benzene; or halocarbons such as dichloromethane or chloroform.
  • the reaction temperature can vary between 0 °C and 150 °C and the reaction time can be from 1 to 72 hours depending on the choice of base, solvent, temperature, and substrates.
  • N-Amino-ureas of Formula 26 can be prepared as illustrated in Scheme 20.
  • Treatment of an aniline of Formula 27 with phosgene, thiophosgene, l,l'-carbonyldiimidazole, or l,l'-(thiocarbonyl)diimidazole produces the isocyanate or isothiocyanate of Formula 28.
  • a base can be added for reactions with phosgene or thiophosgene.
  • Subsequent treatment of the iso(thio)cyanate with an R -substituted hydrazine produces the N-amino-urea of Formula 26.
  • Compounds of Formula 30 can be prepared from corresponding nitrobenzyl alcohols of Formula 30a (compounds of Formula 30 where the Lg group has been replaced with OH) by reaction with halogenating agents such as thionyl chloride or phosphorus oxybromide to form the corresponding ⁇ -halo-substituted derivatives (Scheme 23).
  • halogenating agents such as thionyl chloride or phosphorus oxybromide
  • Compounds of Formula 30a can also be treated with an sulfonyl halide or haloalkylsulfonyl anhydride, such as methane sulfonyl chloride, jc-toluenesulfonyl chloride, and trifluoromethanesulfonyl anhydride, to form the corresponding ⁇ -sulfonate of Formula 30.
  • the reaction with the sulfonyl halides may be performed in the presence of a suitable base (e.g., triethylamine).
  • the (thio)ureas of Formula 32 can be prepared by either of the methods illustrated in Scheme 26.
  • the anilines of Formula 27 can be contacted with an isocyanate or isothiocyanate of Formula 35 as described above.
  • an iso(thio)cyanate of Formula 28 can be condensed with an amine of Formula R 2 -NH 2 to form the urea.
  • the anilines and iso(thio)cyanates of Formulae 27 and 28, respectively, are commercially available or prepared by well-known methods.
  • isothiocyanates can be prepared by methods described in J. Heterocycl. Chem. 1990, 27, 407.
  • Isocyanates can be prepared as described in March, J. Advanced Organic Chemistry; 3rd ed., John Wiley: New York, 1985; 944, 1166.
  • Formula 17 or 18 with nucleophilic compounds of Formula 37 affords compounds of Formula Ii.
  • a base for example sodium hydride, is used to generate the corresponding alkoxide or thioalkoxide of the compounds of Formula 37.
  • an additional substituent on Z which activates the leaving group (Lg) can be advantageous (e.g., when Lg-Z is 2-chloro-3-nitrothiophene, the activating nitro group can be removed after coupling by reduction to the amine followed by diazotization and reduction to provide compounds of Formula Ii).
  • Benzyl halides of Formula 38 can be prepared by radical halogenation of the corresponding alkyl compound of Formula 39a, see WO 96/38425. Benzyl halides can also be prepared by the acidic cleavage of the corresponding methyl ether of Formula 39b under conditions which provide the halide, see Scheme 30. Methods for preparing the corresponding compounds of Formula 38 wherein the T 1 group has been replaced by T 2 are described in WO 94/05620. Methods for preparing the corresponding compounds of Formula 38 wherein the T 1 group has been replaced by T 3 are described in EP-A-254,426, EP-A-299,694 and AU-A-55899/90.
  • compounds of Formula 38 can be prepared from the corresponding alcohol of Formula 40 by reaction with halogenating agents such as thionyl chloride or phosphorus oxybromide to form the corresponding ⁇ -halo-substituted derivatives.
  • compounds of Formula 40 can be treated with an sulfonyl halide or haloalkylsulfonyl anhydride, such as methane sulfonyl chloride, >-toluenesulfonyl chloride, and trifluoromethanesulfonyl anhydride, to form the corresponding ⁇ -sulfonate of Formula 41.
  • the reaction with the sulfonyl halides may be performed in the presence of a suitable base (e.g., triethylamine) see Scheme 31.
  • Compounds of Formula 40 can be prepared by reducing esters of Formula 44 or aldehydes of Formula 43 with an appropriate reducing agent, (M. Hudlicky, Reductions in Organic Chemistry; John Wiley & Sons, 1986; 147-160).
  • diisobutylaluminum hydride DIBAL-H
  • DIBAL-H diisobutylaluminum hydride
  • Compounds of Formula 43 can be reduced with sodium borohydride in a protic solvent such as methanol or ethanol, Scheme 33.
  • Esters of Formula 44 can be prepared from aminobenzoic acid esters of Formula 45 according to the procedures described in Scheme 34.
  • Esters 45 can be prepared from readily accessible aminobenzoic acids by esterification techniques well known in the art.
  • a formaldehyde equivalent i.e., NN-dimethylformamide or methyl chloroformate
  • compounds of Formula 48 can be prepared from compounds of Formula 46 by metallation using an alkyllithium followed by quenching with a trialkoxy borane, (Scheme 37), see Organic Synthesis via Boranes; Wiley: New York, 1975.
  • Compounds of Formula Im can be prepared from compounds of Formula Ik by catalytic hydrogenation, see Rylander, P. N. Catalytic Hydrogenation in Organic Synthesis,
  • R20 P(C 6 H 5 ) 3 + (CI, Br or l) - O
  • R20 P(O(C ⁇ -C4 a-kyl))
  • the olefin of Formula Ik can also be prepared by reversing the reactivity of the reactants in the Wittig or Horner-Emmons condensation.
  • 2-alkylphenyl derivatives of Formula 54 can be converted into the corresponding dibromo-compounds of Formula 53a as illustrated in Scheme 40 (see Synthesis 1988, 330).
  • the dibromo-compounds can be hydrolyzed to the carbonyl compounds of Formula 53b, which in turn can be condensed with a phosphorus-containing nucleophile of Formula 56 or 57 to afford the olefins of Formula Ik.
  • NBS N-bromosuccinimide 55b
  • Carbamates of Formula lo can be prepared by reacting benzyl alcohols of Formula 59 (compounds of Formula II wherein Y 1 is CH(R 11 )OH) with iso(thio)cyanates of Formula 60 (Scheme 42).
  • a base such as triethylamine can be added to catalyze the reaction.
  • Compounds of Formula Ip may be prepared by methods described in EP-A- 178,826, EP-A-341,845 and EP-A-464,381.
  • a triarylbismuth compound or a substituted phenylboronic acid in the presence of cupric acetate and a tertiary amine such as pyridine or triethylamine as illustrated in Scheme 44.
  • organobismuth reagents in the preparation of diaryl ethers is well known in the art (see Tetrahedron Lett. 1986, 27,
  • Y8 -O- It is recognized that some reagents and reaction conditions described above for preparing compounds of Formula I may not be compatible with certain functionalities present in the intermediates. In these instances, the incorporation of protection/dep otection sequences or functional group interconversions into the synthesis will aid in obtaining the desired products. The use and choice of the protecting groups will be apparent to one skilled in chemical synthesis (see, for example, Greene, T. W.; Wuts, P. G. M. Protective Groups in Organic Synthesis, 2nd ed.; Wiley: New York, 1991).
  • methoxymethyl triphenylphosphonium chloride 24 g, 0.07 mol was added portion-wise to a solution of potassium tert-butoxide (7.8 g, 0.07 mol in 300 mL dry diethyl ether at 5 °C. The reaction then stirred at room temperature for 1 h. Then the title compound from Example 1, Step A above (11.1 g, 0.0578 mol) was added and the reaction stirred at room temperature for 18 h. The reaction was washed with water, dried over magnesium sulfate and concentrated to an oil. This crude oil was then purified via column chromatography using 4:l/hexanes:ethyl acetate to yield 1.9 g of pure title compound as an oil.
  • Step B Preparation of (EVmethyl 5-(bromomethyl)- ⁇ -(methoxymethylene)-2- methylbenzeneacetate
  • the title compound from Step A above (Example 2) (1.9 g, 0.0086 mol ), N-bromosuccinimide (1.54 g, 0.0086 mol) and 10 mg of 2,2'-azobisisobutyronitrile (AIB ⁇ ) were combined in 40 mL carbon tetrachloride and refluxed under nitrogen for 6 h, cooled to room temperature and concentrated to an oil. The crude oil was then purified via column chromatography using 4:l/hexanes:ethyl acetate as the eluent to give 0.10 g oil of the title compound.
  • J H ⁇ MR (CDC1 3 ) ⁇ 3.7(s, 3H), 3.8 (s, 3H), 4.45 (s, 2H), 7.1 (s, IH), 7.2-7.3 (m, 2H), 7.6 (s, IH).
  • Step C Preparation of (E)-methyl ⁇ -(methoxymethylene)-2-methyl-5-IT.T 1 -13-
  • O- z 3-SCHF 2 -phenyl 4-SCH 3 - ⁇ henyl
  • O- z 4-OCF 3 -phenyl 3-/-Bu-phenyl
  • O- z 5-OCF 3 -2-thiazolyl 5-(CH 3 ) 3 Si-2-thiazolyl
  • ⁇ 0- z 5-Me-3-thienyl 5-(CH 3 ) 3 C-3-thienyl
  • ⁇ o- z 4-(CH 3 ) 3 C-3-thienyl 4-Cl-3-thienyl

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  • Life Sciences & Earth Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Agronomy & Crop Science (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
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  • Plural Heterocyclic Compounds (AREA)

Abstract

Composés de formule (I), ainsi que leurs N-oxydes et les sels adaptés sur le plan agricole desdits composés, qui sont utiles en tant que fongicides et arthropodicides. Dans ladite formule, T est T?1, T2, T3 ou T4¿; YZ est un groupe constitué de (a) 3 atomes ou plus indépendamment sélectionnés dans le groupe constitué par C, N, O, S, Si et Ge, à condition qu'au moins 2 desdits atomes soient C, et (b) d'atomes supplémentaires choisis parmi H, F, Cl, Br et I; R3 est halogène, CF¿3?, alkyle C1-C3 ou alcoxy C1-C3; R?4¿ est H, halogène, CF¿3?, alkyle C1-C3 ou alcoxy C1-C3; et A, G, W, X, R?1, R2, R5, R6¿ et s sont tels que définis dans le descriptif. La présente invention concerne également des compositions contenant les composés de formule (I), un procédé de lutte contre les maladies des plantes causées par des agents fongiques pathogènes des végétaux, qui consiste à appliquer une quantité efficace d'un composé de formule (I), un procédé de lutte contre les arthropodes qui consiste à mettre les arthropodes ou leur environnement en contact avec une quantité efficace d'un composé de formule (I), ainsi que des composés de formule (II) telle que définie dans le descriptif et l'utilisation de ces derniers pour produire des composés de formule (I).
PCT/US1998/024265 1997-12-01 1998-11-13 Amides cycliques fongicides WO1999028305A1 (fr)

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Cited By (15)

* Cited by examiner, † Cited by third party
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JP2003507368A (ja) * 1999-08-18 2003-02-25 アベンティス クロップサイエンス ゲゼルシャフト ミット ベシュレンクテル ハフツング 殺真菌剤
US6824830B1 (en) * 1999-10-20 2004-11-30 Aventis Cropscience Gmbh Wood treatment
WO2008124092A2 (fr) 2007-04-03 2008-10-16 E. I. Du Pont De Nemours And Company Fongicides contenant du benzène substitué
JP2008540474A (ja) * 2005-05-14 2008-11-20 バイエル・クロツプサイエンス・アクチエンゲゼルシヤフト 置換されたアリールオキシム
US7838541B2 (en) 2002-02-11 2010-11-23 Bayer Healthcare, Llc Aryl ureas with angiogenesis inhibiting activity
US7897623B2 (en) 1999-01-13 2011-03-01 Bayer Healthcare Llc ω-carboxyl aryl substituted diphenyl ureas as p38 kinase inhibitors
US20120004381A1 (en) * 2009-01-23 2012-01-05 Commonwealth Scientific And Industrial Research Organisation Raft polymerisation
US8124630B2 (en) 1999-01-13 2012-02-28 Bayer Healthcare Llc ω-carboxyaryl substituted diphenyl ureas as raf kinase inhibitors
JP2012530751A (ja) * 2009-06-24 2012-12-06 エフ．ホフマン−ラ ロシュ アーゲー 複素環式の抗ウイルス性化合物
WO2013115391A1 (fr) * 2012-02-01 2013-08-08 日本農薬株式会社 Dérivé d'arylalkyloxy pyrimidine, pesticide à usage agricole et horticole contenant le dérivé d'arylalkyloxy pyrimidine comme ingrédient actif, et son utilisation
US8637553B2 (en) 2003-07-23 2014-01-28 Bayer Healthcare Llc Fluoro substituted omega-carboxyaryl diphenyl urea for the treatment and prevention of diseases and conditions
US8796250B2 (en) 2003-05-20 2014-08-05 Bayer Healthcare Llc Diaryl ureas for diseases mediated by PDGFR
WO2015102104A1 (fr) * 2014-01-06 2015-07-09 住友化学株式会社 Composés de thiazole et applications de lutte antiparasitaire correspondantes
WO2021153786A1 (fr) * 2020-01-31 2021-08-05 住友化学株式会社 Dérivé d'acide phénylacétique, utilisation associée et intermédiaire de production associé
WO2022181793A1 (fr) * 2021-02-26 2022-09-01 住友化学株式会社 Dérivé d'acide phénylacétique, utilisation associée et intermédiaire de production associé

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0178826A2 (fr) * 1984-10-19 1986-04-23 Zeneca Limited Fongicides
US5194662A (en) * 1990-06-27 1993-03-16 Basf Aktiengesellschaft O-benzyloxime ethers and crop protection agents containing these compounds
US5286750A (en) * 1989-10-11 1994-02-15 Basf Aktiengesellschaft Phenylacetic acid derivatives and fungicides containing them
WO1996036615A1 (fr) * 1995-05-16 1996-11-21 E.I. Du Pont De Nemours And Company Amides cycliques fongicides

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0178826A2 (fr) * 1984-10-19 1986-04-23 Zeneca Limited Fongicides
US5286750A (en) * 1989-10-11 1994-02-15 Basf Aktiengesellschaft Phenylacetic acid derivatives and fungicides containing them
US5194662A (en) * 1990-06-27 1993-03-16 Basf Aktiengesellschaft O-benzyloxime ethers and crop protection agents containing these compounds
WO1996036615A1 (fr) * 1995-05-16 1996-11-21 E.I. Du Pont De Nemours And Company Amides cycliques fongicides

Cited By (29)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8124630B2 (en) 1999-01-13 2012-02-28 Bayer Healthcare Llc ω-carboxyaryl substituted diphenyl ureas as raf kinase inhibitors
US8841330B2 (en) 1999-01-13 2014-09-23 Bayer Healthcare Llc Omega-carboxyaryl substituted diphenyl ureas as raf kinase inhibitors
US7897623B2 (en) 1999-01-13 2011-03-01 Bayer Healthcare Llc ω-carboxyl aryl substituted diphenyl ureas as p38 kinase inhibitors
JP2003507368A (ja) * 1999-08-18 2003-02-25 アベンティス クロップサイエンス ゲゼルシャフト ミット ベシュレンクテル ハフツング 殺真菌剤
JP4965779B2 (ja) * 1999-08-18 2012-07-04 バイエル・クロップサイエンス・アーゲー 殺真菌剤
US6824830B1 (en) * 1999-10-20 2004-11-30 Aventis Cropscience Gmbh Wood treatment
US8618141B2 (en) 2002-02-11 2013-12-31 Bayer Healthcare Llc Aryl ureas with angiogenesis inhibiting activity
US7838541B2 (en) 2002-02-11 2010-11-23 Bayer Healthcare, Llc Aryl ureas with angiogenesis inhibiting activity
US8242147B2 (en) 2002-02-11 2012-08-14 Bayer Healthcare Llc Aryl ureas with angiogenisis inhibiting activity
US8796250B2 (en) 2003-05-20 2014-08-05 Bayer Healthcare Llc Diaryl ureas for diseases mediated by PDGFR
US8637553B2 (en) 2003-07-23 2014-01-28 Bayer Healthcare Llc Fluoro substituted omega-carboxyaryl diphenyl urea for the treatment and prevention of diseases and conditions
JP2008540474A (ja) * 2005-05-14 2008-11-20 バイエル・クロツプサイエンス・アクチエンゲゼルシヤフト 置換されたアリールオキシム
WO2008124092A2 (fr) 2007-04-03 2008-10-16 E. I. Du Pont De Nemours And Company Fongicides contenant du benzène substitué
EP2430920A2 (fr) 2007-04-03 2012-03-21 E.I. Du Pont De Nemours And Company Fongicides de benzène substitués
EP2430921A2 (fr) 2007-04-03 2012-03-21 E.I. Du Pont De Nemours And Company Fongicides de benzène substitués
US20120004381A1 (en) * 2009-01-23 2012-01-05 Commonwealth Scientific And Industrial Research Organisation Raft polymerisation
US9340498B2 (en) * 2009-01-23 2016-05-17 Commonwealth Scientific And Industrial Reserach Organisation Raft polymerisation
JP2012530751A (ja) * 2009-06-24 2012-12-06 エフ．ホフマン−ラ ロシュ アーゲー 複素環式の抗ウイルス性化合物
CN104185628A (zh) * 2012-02-01 2014-12-03 日本农药株式会社 芳基烷氧基嘧啶衍生物、含有芳基烷氧基嘧啶衍生物作为活性成分的农业和园艺用杀虫剂、以及它们的用途
WO2013115391A1 (fr) * 2012-02-01 2013-08-08 日本農薬株式会社 Dérivé d'arylalkyloxy pyrimidine, pesticide à usage agricole et horticole contenant le dérivé d'arylalkyloxy pyrimidine comme ingrédient actif, et son utilisation
CN104185628B (zh) * 2012-02-01 2017-03-08 日本农药株式会社 芳基烷氧基嘧啶衍生物、含有芳基烷氧基嘧啶衍生物作为活性成分的农业和园艺用杀虫剂、以及它们的用途
US9750252B2 (en) 2012-02-01 2017-09-05 Nihon Nohyaku., Ltd. Arylalkyloxy pyrimidine derivative, pesticide for agricultural and horticultural use containing arylalkyloxy pyrimidine derivative as active ingredient, and use of same
WO2015102104A1 (fr) * 2014-01-06 2015-07-09 住友化学株式会社 Composés de thiazole et applications de lutte antiparasitaire correspondantes
CN105873911A (zh) * 2014-01-06 2016-08-17 住友化学株式会社 噻唑化合物及其有害生物防除用途
JPWO2015102104A1 (ja) * 2014-01-06 2017-03-23 住友化学株式会社 チアゾール化合物及びその有害生物防除用途
US9730449B2 (en) 2014-01-06 2017-08-15 Sumitomo Chemical Company, Limited Thiazole compound and its use in pest control
CN105873911B (zh) * 2014-01-06 2018-07-24 住友化学株式会社 噻唑化合物及其有害生物防除用途
WO2021153786A1 (fr) * 2020-01-31 2021-08-05 住友化学株式会社 Dérivé d'acide phénylacétique, utilisation associée et intermédiaire de production associé
WO2022181793A1 (fr) * 2021-02-26 2022-09-01 住友化学株式会社 Dérivé d'acide phénylacétique, utilisation associée et intermédiaire de production associé

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