[go: up one dir, main page]

WO2004058724A1 - Compose phenylpyrazole et methode de lutte contre une maladie vegetale au moyen de ce dernier - Google Patents

Compose phenylpyrazole et methode de lutte contre une maladie vegetale au moyen de ce dernier Download PDF

Info

Publication number
WO2004058724A1
WO2004058724A1 PCT/JP2003/016076 JP0316076W WO2004058724A1 WO 2004058724 A1 WO2004058724 A1 WO 2004058724A1 JP 0316076 W JP0316076 W JP 0316076W WO 2004058724 A1 WO2004058724 A1 WO 2004058724A1
Authority
WO
WIPO (PCT)
Prior art keywords
group
compound
hydrogen atom
formula
atom
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/JP2003/016076
Other languages
English (en)
Japanese (ja)
Inventor
Hiroshi Sakaguchi
Takashi Komori
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Sumitomo Chemical Co Ltd
Original Assignee
Sumitomo Chemical Co Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Sumitomo Chemical Co Ltd filed Critical Sumitomo Chemical Co Ltd
Priority to AU2003289105A priority Critical patent/AU2003289105A1/en
Publication of WO2004058724A1 publication Critical patent/WO2004058724A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D231/38—Nitrogen atoms
    • C07D231/40—Acylated on said nitrogen atom
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles

Definitions

  • the present invention relates to a phenylpyrazole compound and a method for controlling plant diseases using the same.
  • the present invention relates to a phenylvirazole compound, and a method for controlling a plant disease which is applied to a plant or soil.
  • Certain phenylpyrazole compounds are known to have physiological activity, but the activity of the compound for controlling plant diseases is not known. Disclosure of the invention
  • the present inventors have conducted intensive studies to find a compound having an excellent plant disease controlling effect, and as a result, have found that the phenylpyrazole compound represented by the following formula (1) has an excellent plant disease controlling effect. Completed the invention.
  • R 6 represents a hydrogen atom or a C 1 -C 3 alkyl group
  • Q is the following Ql, ⁇ 32 or (33
  • Z 1 represents an oxygen atom or a sulfur atom
  • R 14 represents a hydrogen atom or a C 1 -C 3 alkyl group
  • R 15 is a hydrogen atom, a CI—C 6 alkyl group, a CI—C 6 haloalkyl group, a C 3 —C 6 Alkenyl group, C3-C6 haloalkenyl group, C3-C6 alkynyl group, C3-C6 haloalkynyl group, C3-C6 cycloalkyl group, (C1-C67 alkyl) carbonyl group, (C 1 -C 6 haloalkyl) carbonyl group, (C 1 -C 6 alkoxy) carbonyl group, (C 1 -C 6 haloalkoxy) carbonyl group, (C 3 -C 6 alkenyloxy) carbonyl group, (C 3 _ C 6 haloalkenyl O carboxymethyl) force Ruponiru
  • R 16 is a hydrogen atom, a C 1 -C 6 alkyl group, a C 1 -C 6 alkenyl group, a C 3 -C 6 alkenyl group, a C 3 -C 6 haloalkenyl group, a C 3 -C 6 alkynyl group, Represents a C3-C6 haloalkynyl group or a C3-C6 cycloalkyl group,
  • R 17 is a halogen atom, (: 1-6 alkyl group, ⁇ 1-6 alkyl group) Group, CI-C6 alkoxy group, C1-C6 haloalkoxy group, C3-C6 alkenyloxy group, C3-C6 haloalkenyloxy group, C3-C6 alkynyloxy group, C 3 _C 6 haloalkynyloxy, hydroxy, di (C 1 -C 3 alkyl) amino or C 3 -C 6 cycloalkyloxy, where R 18 is a hydrogen atom, a halogen atom, a CI-C 6 alkyl Group or a C1-C6 haloalkyl group,
  • R 21 represents a hydrogen atom, a C 1 -C 4 alkyl group, a C 3 -C 4 alkenyl group or a C 3 -C 4 alkynyl group. ⁇ . ]
  • a phenylpyrazole compound hereinafter, referred to as the compound of the present invention
  • a plant disease controlling composition containing the compound of the present invention as an active ingredient
  • a method for controlling a disease is provided. Specific examples of the substituents in the formula (1) of the present invention are shown below.
  • halogen atom examples include a fluorine atom, a chlorine atom and a bromine atom
  • C1-C6 alkyl group examples include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group and a sec-butyl group.
  • C1-C6 octaalkyl groups include fluoromethyl, difluoromethyl, trifluoromethyl, chlorodifluoromethyl, chlorofluoromethyl, bromodifluoromethyl, trichloromethyl, dichlorobromomethyl Group, pentafluoroethyl, 2,2,2-trifluoroethyl, 1,1-difluoroethyl, 2,2-difluoroethyl, 2-fluoroethyl and 6,6,6-trifluoroethyl A hexyl group,
  • Examples of the C2-C6 alkenyl group include a vinyl group, a 1-propenyl group, a 2-propyl group, a 1-methyl-1-propenyl group, a 1-methyl_2-propenyl group, Me Cyl-1-propenyl, 2-methyl-2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-hexenyl, 2-hexenyl and 5-hexenyl Given
  • Examples of the C2-C6 haloalkenyl group include 1-chlorovinyl group, 2-chlorovinyl group, 2,2-dichlorovinyl group, 2,2-difluorovinyl group, 1,2-dichlorovinyl group, 3,3- Dichloro-2-propenyl group and 3,3-difluoro-2-propenyl group;
  • Examples of the C 2 -C 6 alkynyl group include an ethynyl group, a 3-butynyl group, a 3-hexynyl group and a 5-hexynyl group.
  • Examples of the C2-C6 haloalkynyl group include a 2-chloroethynyl group, a 2-bromoethynyl group, a 3-chloro-2-propynyl group, a 3-bromo-2-propynyl group and a 6-chloro-5-hexynyl group,
  • C 11 -C 6 alkoxy groups include methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, sec-butoxy, tert-butoxy, pentyloxy, isopentyloxy and hexyloxy.
  • C 11 -C 6 haloalkoxy groups include trifluoromethoxy group, difluoromethoxy group, bromodifluoromethoxy group, chlorodifluoromethoxy group, fluoromethoxy group, 2,2,2-trifluoroethoxy group , 1,1,2,2-tetrafluoroethoxy group, 5-chloropentyloxy group, 4-fluoro-3-methylbutoxyoxy group and 2,2-dichlorohexyloxy group,
  • Examples of the C 3 -C 6 alkenyloxy group include 2-propenyloxy group, 1-methyl-12-propenyloxy group, 2-methyl-2-propenyloxy group, 2-butenyloxy group, and 3-butenyloxy group.
  • Examples of the C 3 -C 6 haloalkenyloxy group include a 3,3-dichloro-1-propenyloxy group, a 3,3-difluoro-2-propenyloxy group, and a 3,3-dibromo-12-propyl group.
  • the C 3 -C 6 alkynyloxy group includes 2-propynyloxy group, 1-methyl-12-propynyloxy group, 2-butynyloxy group, 3-butynyloxy group, 2 A hexynyloxy group and a 5-hexynyloxy group;
  • Examples of the C 3 -C 6 haloalkynyloxy group include a 3-chloro-2-propynyloxy group, a 3-bromo-2-propynyloxy group, a 3-odo-2-propynyloxy group, and a 6-chloro-5-hexynyloxy group.
  • Examples of the C 1 -C 3 acyl group include a formyl group, an acetyl group, and a propionyl group.
  • C 1 -C 3 alkoxyimino C 1 -C 3 acyl group includes methoxyiminomethyl group, ethoxyiminomethyl group, 1-methoxyiminoethyl group, and C 1 -C 6 alkylthio group includes Methylthio, ethylthio, propylthio, isopropylthio, butylthio, isobutylthio, sec-butylthio, tert-butylthio, pentylthio, isopentylthio, and hexylthio;
  • C 11 -C 6 haloalkylthio groups include trifluoromethylthio, difluoromethylthio, bromodifluoromethylthio, chlorodifluoromethylthio, fluoromethylthio, and 2,2,2-trifluoroethyl Cylthio, 1,1,2,2-tetrafluoroethylthio, 5-chloropentylthio, 4-fluoroisopentylthio, and 2,2-dichlorohexylthio;
  • Examples of the 3-C 6 cycloalkyl group include a cyclopropyl group, a cyclopentyl group and a cyclohexyl group,
  • Examples of the C 3 -C 6 cycloalkoxy group include a cyclopropoxy group, a cyclopentyloxy group, and a cyclohexyloxy group.
  • Examples of the C 11 -C 3 alkyl group include a methyl group, an ethyl group and a propyl group.
  • Examples of the C1-C6 alkoxy group include a methoxy group, an ethoxy group, a propoxy group, an isopropoxy group, a butoxy group, an isobutoxy group, a sec-butoxy group, a tert-butoxy group, a pentyloxy group, an isopentyloxy group, and a hexyloxy group. Group.
  • Examples of the C 11 -C 6 haloalkoxy group include a trifluoromethoxy group, a difluoromethoxy group, a bromodifluoromethoxy group, a chlorodifluoromethoxy group, a fluoromethoxy group, a 2,2,2-trifluoroethoxy group. , 1, 1, 2, 2—tetra A fluoroethoxy group, a 5-cyclopentyloxy group, a 4-fluoro-3-methylbutoxyoxy group and a 2,2-dichlorohexyloxy group,
  • Examples of the C 3 -C 6 alkenyloxy group include 2-propenyloxy group, 1-methyl-12-propenyloxy group, 2-methyl-2-propenyloxy group, 2-butenyloxy group, and 3-butenyloxy group. , 2-hexenyloxy and 5-hexenyloxy groups,
  • Examples of the C 3 -C 6 alkynyloxy group include a 2-propieroxy group, a 1-methyl-12-propynyloxy group, a 2-butynyloxy group, a 3-butenyloxy group, a 2-hexyloxy group and a 5-hexyloxy group.
  • Examples of the C1-C6 alkyl group include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, a pentyl group, an isopentyl group and a hexyl group.
  • Examples of the C3-C6 alkenyl group include 2-propenyl, 1-methyl-2-propyl, 1,1-dimethyl-2-propyl, 2-methyl-2-propyl, and 2-methyl-2-propyl.
  • -Butenyl group, 3-butenyl group, 2-hexenyl group and 5-hexenyl group are examples of the C3-C6 alkenyl group.
  • C3-C6 alkynyl groups include 2_propynyl group, 1-methyl-2-propynyl group, 1,1-dimethyl-2-propynyl group, 2-butynyl group, 3-butynyl group and 2-hexynyl group And 5-hexynyl group;
  • Examples of the C 3 -C 6 haloalkynyl group include a 3-chloro-2-propenyl group, a 3-bromo2-propynyl group and a 6-chloro-5-hexyl group, and C 3 -C 6
  • Examples of the cycloalkyl group include a cyclopropyl group, a cyclopentyl group, and a cyclohexyl group.
  • (C 1 -C 6 alkyl) carbonyl groups include acetyl, ethylcarbonyl, propylcarbonyl, isopropylcarbonyl, butylcarbonyl, isobutylcarbonyl, sec-butylcarbonyl, tert-butylcarbonyl, pentylcarbonyl , Isopentyl carbonyl group and hexyl carbonyl group,
  • the carbonyl group includes chloroacetyl, bromoacetyl, difluoroacetyl, trifluoroacetyl, trichloroacetyl, chlorofluoroacetyl, bromodifluoroacetyl, 2-fluoroethylcarbonyl, 2,2 difluoroethylcarbonyl, 2,2,2-trifluoroethylcarbonyl and 6,6,6-trifluorohexylcarbonyl;
  • the carbonyl group includes a methoxycarbonyl group, an ethoxycarbonyl group, a propoxycarbonyl group, an isopropoxycarbonyl group, a butoxycarbonyl group, an isobutoxycarbonyl group, a sec-butoxycarbonyl group, and a tert-carbonyl group.
  • (C 1 -C 6 haloalkoxy) carbonyl groups include 2,2,2-trifluoro-mouth ethoxycarbonyl group, 1,1,2,2-tetrafluoroethoxycarbonyl group, and 5-cyclopentyloxycarbonyl group And 2,2-dichlorohexyloxycarponyl groups,
  • (C 3 -C 6 alkenyloxy) carbonyl group includes 2-propenyloxycarbonyl group, 1-methyl-2-propenyloxycarbonyl group, 2-methyl-2-propenyloxycarbonyl group, 2-butenyloxycarbonyl group, 3-butane Tenyloxycarbonyl, 2-hexenyloxycarbonyl and 5-hexenyloxycarbonyl,
  • (C3-C6 haloalkenyloxy) carbonyl groups include 3-chloro-2-propynyloxycarbonyl group, 3-bromo-2-propieroxycarbonyl group, and 3-odo-2-propynyloxy group. And a 6-chloro-5-hexenyloxycarbonyl group,
  • (C3-C6-haloalkynyloxy) carbonyl group includes 3-chloro-2-propieroxycarbonyl, 3-bromo-2-propieroxycarbonyl group, 3-odo-2-propynyloxy group A luponyl group and a 6-chloro-5-hexynyloxycarbonyl group,
  • Examples of the C 1 -C 3 alkylsulfonyl group include a methanesulfonyl group and an ethanesulfonyl group.
  • C 1 -C 6 alkyl groups include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec.ec-butyl, tert-butyl, pentyl, isopentyl and hexyl.
  • Examples of the C 1 -C 6 haloalkyl group include a fluoromethyl group, a difluoromethyl group, a 2-fluoroethyl group, a 2,2-difluoroethyl group, a 2,2,2-trifluoroethyl group and a 6,6,6-trifluorohexyl group. Is raised,
  • C3-C6 alkenyl groups include 2-propenyl, 1-methyl-2-probenyl, 2-methyl-2-propenyl, 2-butenyl, 3-butenyl, A hexenyl group and a 5-hexenyl group,
  • Examples of the C3-C6 haloalkenyl group include a 2,3-dichloropropenyl group, a 3,3-dichloropropenyl group, and a 3,3-difluoropropenyl group
  • C3-C6 Alkynyl groups include 2-propynyl group, 1-methyl-2-propynyl group, 1,1-dimethyl-2-propynyl group, 2-butynyl group, 3-butenyl group, 2-hexynyl group and 5-hexynyl group.
  • C3-C6 haloalkynyl groups include 3-chloro-2-propynyl group and 3-butyl Mouth 2-propynyl and 6-chloro-5-hexynyl groups can be mentioned, and C3-C6 cycloalkyl groups include cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl. Is raised.
  • halogen atom examples include a fluorine atom, a chlorine atom and a bromine atom.
  • Examples of the C1-C6 alkyl group include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, a pentyl group, an isopentyl group and a hexyl group.
  • the C 3 -C 6 alkynyloxy group includes 2-propynyloxy group, 1-methyl-2-propynyloxy group, 2-butynyloxy group, 3-butynyloxy group, 2-hexynyloxy group and 5-hexynyloxy group.
  • Group, Examples of the C3-C6 haloalkynyloxy group include 3-chloro-2-propynyloxy, 3-bromo-2-propynyloxy, 3-odo-2-propynyloxy and 6-chloro-5. — A hexynyloxy group;
  • Examples of the C 3 -C 6 cycloalkyloxy group include a cyclopropyloxy group, a cyclobutyloxy group, a cyclopentyloxy group and a cyclohexyloxy group.
  • C1-C6 alkyl groups include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, pentyl, iso-benzyl and hexyl.
  • Examples of the C3-C4 alkenyl group include a 2-propenyl group, a 1-methyl-2-probenyl group, a 2-methylene 2-probenyl group, a 2-butenyl group, and a 3-butenyl group.
  • R 1 R 2 , R 4 and R 5 are hydrogen atoms
  • R 3 is a nitrogen atom, a CI—C6 alkyl group, a C 1—C 6 haloalkyl group, a C 2—C 6 alkenyl Group, C2-C6 haloalkenyl group, C2-C6 alkynyl group, C2-C6 haloalkenyl group, C1-C6 alkoxy group, C1-C6 haloalkoxy group, C3-C6 alkenyloxy group , C3-C6 haloalkenyloxy, C3-C6 alkynyloxy, C3-C6 haloalkynyloxy, C1-C6 alkylthio, C1-C6 haloalkylthio, C3- A phenylvinylazole compound which is a C 6 cycloalkyl group, a 3-cyclohexoxy group or a cyano group
  • a phenylvirazole compound wherein R 6 is a hydrogen atom and RR 2 , R 4 and R 5 are hydrogen atoms;
  • X is an oxygen atom
  • RR 4 and R 5 are hydrogen atoms
  • R 9 and R 1 () are methoxy groups
  • R 3 is a halogen atom, a C 1 -C 6 alkyl group, a CI-C 6 haloalkyl group, a CI-C 6 alkoxy group, a C 1 -C 6 alkylthio group or a cyano group, and R 9 and R 1 (a phenylvirazole compound wherein l is a C 1 -C 4 alkoxy group;
  • RR 2 , R 4 and R 5 are a hydrogen atom, and R 9 and R 9 are a C 1 -C 4 alkoxy group.
  • X is an oxygen atom
  • RR 4 and R 5 are hydrogen atoms
  • R 9 and R lfl are methoxy
  • X is an oxygen atom
  • R 6 is a hydrogen atom
  • Z 2 is NO A phenylpyrazole compound which is R 16 ;
  • X is an oxygen atom
  • R 6 is a hydrogen atom
  • R 14 is a hydrogen atom
  • Z 1 is an oxygen atom
  • R 3 is a halogen atom, C 1 —C 6 An alkyl group, a C1-C6 haloalkyl group, a C1-C6 alkoxy group,.
  • a phenylvirazole compound which is a 1-6 alkylthio group or a cyano group, and wherein R 1 R 2 , R 4 and R 5 are hydrogen atoms;
  • X is an oxygen atom
  • R 6 is a hydrogen atom
  • R 14 is a hydrogen atom
  • Z 1 is an oxygen atom
  • R 15 is a methyl group
  • R 3 There halogen atom, C 1 one C 6 alkyl group, C 1-C 6 haloalkyl group, C 1-C6 alkoxy group, a C 1-C 6 alkylthio group or Shiano group, water atom RRR 4 and R 5
  • a phenylpyrazole compound which is
  • X is an oxygen atom
  • R 6 is a hydrogen atom
  • R 14 is a hydrogen atom
  • Z 1 is an oxygen atom
  • R 9 and R 1 () are C 1 A phenylpyrazole compound which is a C 4 alkoxy group
  • X is an oxygen atom
  • R 6 is a hydrogen atom
  • R 14 is a hydrogen atom
  • Z 1 is an oxygen atom
  • R 15 is a 2-propynyl group
  • X is an oxygen atom
  • R 6 is a hydrogen atom
  • R 14 is a hydrogen atom
  • Z 1 is an oxygen atom
  • R 15 is a 2-propynyl group
  • X is an oxygen atom
  • R 6 is a hydrogen atom
  • R 14 is a hydrogen atom
  • Z 1 is an oxygen atom
  • R 15 is a methyl group
  • RR 2 A phenylpyrazole compound wherein R 4 and R 5 are hydrogen atoms, and R 9 and R 1 () are C 1 -C 4 alkoxy groups;
  • X is an oxygen atom
  • R 6 is a hydrogen atom
  • R 14 is a hydrogen atom
  • Z 1 is an oxygen atom
  • R 15 is a 2-propynyl group
  • X is an oxygen atom
  • R 6 is a hydrogen atom
  • R 14 is a hydrogen atom
  • Z 1 is an oxygen atom
  • R 15 is a methyl group
  • RR 2 , R 4 and R 5 are hydrogen atoms
  • R 9 and R 1 (a phenylpyrazole compound wherein 1 is a methoxy group
  • X is an oxygen atom
  • R 6 is a hydrogen atom
  • R 14 is a hydrogen atom
  • Z 1 is an oxygen atom
  • R 15 is a methyl group
  • R 3 There halogen atom, CI- C 6 alkyl group, C 1-C 6 haloalkyl group, a C 1-C6 alkoxy group, C 1 one C 6 alkylthio group or Shiano group, RR 2, R 4 and R 5 water
  • R 9 and R 1 () are each a methoxy group
  • R 6 is a hydrogen atom
  • R 14 is a hydrogen atom
  • Z 1 is an oxygen atom
  • R 6 is a hydrogen atom
  • R 14 is a hydrogen atom
  • Z 1 is an oxygen atom
  • R 15 is a methyl group
  • R 6 is a hydrogen atom
  • R 14 is a hydrogen atom
  • Z 1 is an oxygen atom
  • R 9 and R 1D are C 1 -C 4 alkoxy groups.
  • R 6 is a hydrogen atom
  • R 14 is a hydrogen atom
  • Z 1 is an oxygen atom
  • R 15 is a 2-propynyl group
  • R 9 and R 1 But C1 one C4 al Phenylpyrazole compounds that are oxy groups;
  • R 6 is a hydrogen atom
  • R 14 is a hydrogen atom
  • Z 1 is an oxygen atom
  • R 15 is a methyl group
  • RR 2 , R 4 and R 5 are A phenylpyrazole compound which is a hydrogen atom
  • R 6 is a hydrogen atom
  • R 14 is a hydrogen atom
  • Z 1 is an oxygen atom
  • R 15 is a 2-propynyl group
  • R 9 and R 1 () are methoxy.
  • R 6 is a hydrogen atom
  • R 14 is a hydrogen atom
  • Z 1 is an oxygen atom
  • R 15 is a methyl group
  • R 9 and R l ° are methoxy groups.
  • a phenylvirazole compound wherein R 6 is a hydrogen atom, Z 2 is NOR 16 , and R 9 and R 10 are C 1 -C 4 alkoxy groups;
  • R 6 is a hydrogen atom
  • R 14 is a hydrogen atom
  • Z 1 is an oxygen atom
  • R 15 is a 2-propynyl group
  • R 6 is a hydrogen atom
  • R 14 is a hydrogen atom
  • Z 1 is an oxygen atom
  • R 15 is a 2-propynyl group
  • R 3 is a halogen atom
  • RR 2 , R and R 5 are hydrogen atoms
  • R 6 is a hydrogen atom
  • R 14 is a hydrogen atom
  • Z 1 is an oxygen atom.
  • R 15 is a methyl group
  • RR 2 , R and R 5 are hydrogen atoms
  • R 6 is a hydrogen atom
  • R 14 is a hydrogen atom
  • Z 1 is an acid
  • RR 2 , R 4 and R 5 are hydrogen atoms
  • R 9 and R 1 () are methoxy groups
  • R 6 is a hydrogen atom
  • an R 14 is a hydrogen atom
  • Z 1 is oxygen radicals
  • R 15 is 2-propynyl group, RR 2,: R 4 and A phenylvirazole compound in which R 5 is a hydrogen atom, and R 9 and R 1 () are methoxy groups
  • R 6 is a hydrogen atom
  • R 14 is a hydrogen atom
  • R 15 is a methyl group
  • RR 2 , R and R 5 are hydrogen atoms
  • R 6 is a hydrogen atom
  • Z 2 is NOR 16
  • RR 2 , R 4 and R 5 are hydrogen atoms
  • R 9 and R 1 () are methoxy groups Phenylpyrazole compounds
  • R ′′ is a hydrogen atom
  • Z 1 is an oxygen atom
  • R 15 is a 2-propynyl group
  • R 9 and R ie are C 1 -C 4 alkoxy groups.
  • R 14 is a hydrogen atom
  • Z 1 is an oxygen atom
  • R 15 is A phenylpyrazole compound which is a 2-propynyl group and R 9 and R 1 () are methoxy groups;
  • R 14 is a hydrogen atom
  • Z 1 is an oxygen atom
  • R 1 R 2 , R and R 5 are hydrogen atoms
  • R 9 and R 1Q are C 1 -C 4 alkoxy groups.
  • R 14 is a hydrogen atom
  • Z 1 is an oxygen atom
  • R 15 is a methyl group
  • RR 2 , R 4 and R 5 are hydrogen atoms
  • R 14 is a hydrogen atom
  • Z 1 is an oxygen atom
  • R 15 is a 2_propynyl group
  • RR 2 , R 4 and R 5 are hydrogen atoms
  • R 9 And a phenylpyrazole compound wherein R 10 is a methoxy group
  • R 14 is a hydrogen atom
  • Z 1 is an oxygen atom
  • R 15 is a 2-propynyl group
  • R 3 is a halogen atom, CI—C6 alkyl group, C 1—C 6 haloalkyl group, C 1 -C 6 alkoxy group, C 1 -C 6 alkylthio group or cyano group
  • RR 2 , R 4 and R 5 are hydrogen atoms
  • R 9 and R 1G are methoxy groups.
  • R 14 is a hydrogen atom
  • Z 1 is an oxygen atom
  • R 15 is a methyl group
  • 1 , R 2 , R 4 and R 5 are hydrogen atoms
  • a phenylvirazole compound wherein Z 2 is NOR 16 and RR 2 , R 4 and R 5 are hydrogen atoms;
  • Z 2 is NOR 16 , and R 9 and R 1Q are methoxy groups.
  • X is an oxygen atom
  • R 6 is a hydrogen atom
  • R 3 and R 1 () are phenylvinylazole compounds
  • R 6 is a hydrogen atom
  • R 3 is a halogen atom, (: 1-6 alkyl group, C 1 -C 6 haloalkyl group, CI—C 6 alkoxy)
  • a phenylpyrazol compound which is a thio group, a CI-C 6 alkylthio group or a cyano group
  • RR 2 , R 4 and R 5 are hydrogen atoms;
  • X is an oxygen atom
  • R 21 is a hydrogen atom
  • a phenylpyrazole compound in which R 21 is a hydrogen atom In the formula (1-3), a phenylpyrazole compound in which R 21 is a hydrogen atom; In the formula (1-3), phenylpyrazole in which X is an oxygen atom and R 21 is a hydrogen atom Lazole compounds;
  • X is an oxygen atom
  • R 3 is a halogen atom, a CI—C 6 alkyl group, a C 1—C 6 haloalkyl group, a C 1—C 6 alkoxy group, a C 1—C 6
  • RR 2 , R 4 and R 5 are hydrogen atoms
  • R 9 is a C 1 -C 4 alkoxy group
  • R lfl is a C 3 -C 4 alkynyloxy group.
  • X is an oxygen atom
  • R 6 is a hydrogen atom
  • R 3 is a genogen, a CI—C6 alkyl group, a C 1—C6 haloalkyl group, a CI—C 6 alkoxy group, a C 1—C 6 alkylthio group or a cyano group;
  • the compound of the present invention can be produced, for example, by (Production method 1) to (Production method 13). '
  • L 1 represents a chlorine atom or a bromine atom
  • reaction is carried out in the presence or absence of a solvent, usually in the presence of a base.
  • the compound (4) can be isolated, for example, by subjecting it to a post-treatment operation described below.
  • the reaction is usually performed in the presence of a solvent.
  • reaction is carried out in the presence or absence of a solvent, usually in the presence of a base.
  • the compound (8) is usually in a proportion of 1 to 10 mol, and the base is usually in a proportion of 1 to 10 mol, per 1 mol of the compound (7).
  • reaction mixture After completion of the reaction, the reaction mixture is subjected to a post-treatment operation such as extraction with an organic solvent, and drying and concentration of the organic layer, whereby the compound (9) can be isolated.
  • Isolated Compound (9) can be further purified by chromatography or recrystallization.
  • Examples of the reducing agent used in the reaction include sodium borohydride and potassium borohydride.
  • Solvents used in the reaction include alcohols such as methanol, ethanol, and 2-propanol; ethers such as 1,4-dioxane, tetrahydrofuran, ethylene glycol dimethyl ether, and tert-butyl methyl ether; hexane, heptane, Examples thereof include aliphatic hydrocarbons such as octane, aromatic hydrocarbons such as toluene and xylene, water, and mixtures thereof.
  • the reaction is usually performed in a solvent.
  • compound (14) and compound (16) are produced by the following method. can do.
  • Aromatic hydrocarbons such as xylene, halogenated hydrocarbons such as chlorobenzene, esters such as butyl acetate and ethyl acetate, nitriles such as acetonitrile, and acids such as N, N-dimethylformamide
  • Aromatic hydrocarbons such as xylene, halogenated hydrocarbons such as chlorobenzene, esters such as butyl acetate and ethyl acetate, nitriles such as acetonitrile, and acids such as N, N-dimethylformamide
  • Aromatic hydrocarbons such as xylene, halogenated hydrocarbons such as chlorobenzene, esters such as butyl acetate and ethyl acetate, nitriles such as acetonitrile, and acids such as N, N-dimethylformamide
  • amides sulfoxides such as dimethyl sulfoxide, and mixtures thereof.
  • the reaction is usually performed in the presence of a solvent, in the presence or absence of a base.
  • Solvents used in the reaction include 1,4-dioxane, tetrahydrofuran, ethers such as ethylene glycol dimethyl ether and tert-butyl methyl ether, aliphatic hydrocarbons such as hexane, heptane and octane, toluene and xylene Aromatic hydrocarbons such as benzene, octogenated hydrocarbons such as benzene, esters such as butyl acetate and ethyl acetate, alcohols such as methanol, ethanol and propanol, nitriles such as acetonitrile, N Acid amides such as N, N-dimethylformamide; sulfoxides such as dimethylsulfoxide; and mixtures thereof.
  • 1,4-dioxane 1,4-dioxane
  • ethers such as ethylene glycol dimethyl ether and tert-butyl methyl ether
  • the amount of the base is usually a catalytic amount to 10 mol per 1 mol of the compound (17). (18) or a salt thereof is usually in a proportion of 1 to 10 mol.
  • the reaction time is usually in the range of 1 to 24 hours, and the reaction temperature is usually in the range of 0 to 150 ° C.
  • reaction mixture After completion of the reaction, the reaction mixture is subjected to a post-treatment operation such as extraction with an organic solvent, washing the organic layer with acidic water and Z or basic water as necessary, followed by drying and concentration.
  • a post-treatment operation such as extraction with an organic solvent, washing the organic layer with acidic water and Z or basic water as necessary, followed by drying and concentration.
  • Compound (19) can be isolated.
  • the isolated compound (19) can be further purified by chromatography, recrystallization and the like.
  • compound (22) can be produced by reacting compound (20) with compound (21).
  • L 3 represents a chlorine atom, a bromine atom and a methanesulfonyloxy group
  • RR 2 , R 3 , R 4 , R 5 , R 6 , R 9 , R 10 , R 14 , R 15 " 1 " and X Represents the same meaning as described above.
  • the reaction is carried out in the presence or absence of a solvent, in the presence or absence of a base.
  • Solvents used in the reaction include ethers such as 1,4-dioxane, tetrahydrofuran, ethylene glycol dimethyl ether and tert-butyl methyl ether; aliphatic hydrocarbons such as hexane, heptane and octane; and toluene.
  • Aromatic hydrocarbons such as xylene, halogenated hydrocarbons such as chlorobenzene, esters such as butyl acetate and ethyl acetate, nitriles such as acetonitrile, and acids such as N, N-dimethylformamide
  • Aromatic hydrocarbons such as xylene, halogenated hydrocarbons such as chlorobenzene, esters such as butyl acetate and ethyl acetate, nitriles such as acetonitrile, and acids such as N, N-dimethylformamide
  • Aromatic hydrocarbons such as xylene, halogenated hydrocarbons such as chlorobenzene, esters such as butyl acetate and ethyl acetate, nitriles such as acetonitrile, and acids such as N, N-dimethylformamide
  • amides sulfoxides such as dimethyl sulfoxide, water, and mixtures thereof.
  • Examples of the base used in the reaction include carbonates such as sodium carbonate and carbonated lime, alkali metal hydrides such as sodium hydride, triethylamine, diisoprom. Tertiary amines such as pyrethylamine, 1,8-diazabicyclo [5.4.0] indeck-7-ene, 1,5-diazabicyclo [4.3.0] non-1-ene and pyridines; Nitrogen-containing aromatic compounds such as 4-dimethylaminopyridine.
  • the compound (21) is usually in a proportion of 1 to 3 mol
  • the base is usually in a proportion of 1 to 3 mol, per 1 mol of the compound (20).
  • the reaction time is usually in the range of 1 to 24 hours, and the reaction temperature is usually in the range of 0 to 150 ° C.
  • the compound (22) can be isolated by subjecting the reaction mixture after completion of the reaction to extraction with an organic solvent and performing post-treatment operations such as drying and concentration of the organic layer.
  • the isolated compound (22) can be further purified by chromatography, recrystallization and the like.
  • compound (25) can be produced by reacting compound (23) with compound (24).
  • L 9 represents a chlorine atom, a bromine atom or a methanesulfonyloxy group, is a C 1 -C 6 alkyl group, a C 1 -C 6 haloalkyl group, a C 3 -C 6 alkenyl group, a C 3 -C 6 haloalkenyl group, C 3- C 6 alkynyl group, a C 3- C 6 Haroaruki alkenyl group or a C 3-C 6 cycloalkyl group, RR 2, R 3, R 4, R 5, R 6, R 9, R 1! 1 and X have the same meaning as described above. ]
  • the reaction is carried out in the presence or absence of a solvent, in the presence or absence of a base.
  • a solvent used in the reaction include 1,4-dioxane, tetrahydrofuran, ethylene glycol dimethyl ether, ethers such as tert-butylmethyl ether, aliphatic hydrocarbons such as hexane, heptane and octane, toluene, Aromatic hydrocarbons such as xylene, halogenated hydrocarbons such as benzene, acetic acid Esters such as butyl and ethyl acetate; nitriles such as acetonitrile; acid amides such as N, N-dimethylformamide; sulfoxides such as dimethyl sulfoxide; and mixtures thereof.
  • Examples of the base used in the reaction include carbonates such as sodium carbonate and potassium carbonate, and alkali metal hydrides such as sodium hydride.
  • the compound (24) is usually in a proportion of 1 to 3 mol, and the base is usually in a proportion of 1 to 10 mol, per 1 mol of the compound (23).
  • the reaction time is usually in the range of 1 to 24 hours, and the reaction temperature is usually in the range of 0 to 150 ° C.
  • the compound (25) can be isolated by subjecting the reaction mixture after completion of the reaction to extraction with an organic solvent and performing post-treatment operations such as drying and concentration of the organic layer.
  • the isolated compound (25) can be further purified by chromatography, recrystallization and the like.
  • compound (29) can be produced by reacting compound (27) with compound (28).
  • L 1 () is a chlorine atom, a bromine atom, an iodine atom, p- toluenesulfonyl O key sheet group, represents a leaving group such as a methanesulfonyl O alkoxy group
  • R 3 4 is C 1 one C 6 alkyl Group, C1-C6 haloalkyl group, C3-C6 alkenyl group, C3-C6 haloalkenyl group, C3-C6 alkynyl group, C3-C6 haloalkynyl group or C3-C6 cyclo group
  • RR 2 , R 3 , R 4 , R 5 , R 6 , R 9 , R 1 () and X have the same meaning as described above.
  • the reaction is carried out in the presence or absence of a solvent, in the presence or absence of a base.
  • Solvents used in the reaction include 1,4-dioxane, tetrahydrofuran, Ethers such as ethylene glycol dimethyl ether and tert-butyl methyl ether; aliphatic hydrocarbons such as hexane, heptane and octane; aromatic hydrocarbons such as toluene and xylene; halogenated carbons such as benzene
  • Examples include hydrogens, esters such as butyl acetate and ethyl acetate, nitriles such as acetonitrile, acid amides such as N, N-dimethylformamide, sulfoxides such as dimethyl sulfoxide, and mixtures thereof.
  • Examples of the base used in the reaction include carbonates such as sodium carbonate and carbonated carbonate, alkali metal hydrides such as sodium hydride, triethylamine, diisopropylethylamine, 1,8-diazabicyclo [5.4.0] indeck-7- And tertiary amines such as 1,5-diazabicyclo [4.3.0] non-5-ene and nitrogen-containing aromatic compounds such as pyridine and 4-dimethylaminopyridine.
  • the compound (28) is usually in a proportion of 1 to 3 mol
  • the base is usually in a proportion of 1 to 5 mol, based on 1 mol of the compound (27).
  • the reaction time is usually in the range of 1 to 24 hours, and the reaction temperature is usually in the range of 0 to 150 ° C.
  • the reaction mixture is subjected to a post-treatment operation such as extraction with an organic solvent and drying and concentration of the organic layer, whereby the compound (29) can be isolated.
  • the isolated compound (29) can be further purified by chromatography, recrystallization, or the like.
  • the reaction is usually carried out in the presence of a solvent.
  • Solvents used in the reaction include acid amides such as N, N-dimethylformamide, sulfoxides such as dimethylsulfoxide, halogenated hydrocarbons such as chloroform and benzene, nitrogen-containing aromatic compounds such as pyridine and quinoline. Group compounds and mixtures thereof.
  • Examples of the dehydrating condensing agent used in the reaction include carpoimides such as 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide hydrochloride (hereinafter, referred to as WSC) and 1,3-dicyclohexylcarposimide.
  • WSC 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide hydrochloride
  • WSC 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide hydrochloride
  • 1,3-dicyclohexylcarposimide 1,3-dicyclohexylcarposimide
  • the amount of the reagent used in the reaction is such that the compound (2-1) is usually in a proportion of 1 to 3 mol and the dehydrating condensing agent is usually in a proportion of 1 to 5 mol per 1 mol of the compound (3).
  • the reaction time is usually in the range of 1 to 24 hours, and the reaction temperature is usually in the range of 0 to 14 Ot :.
  • the compound (4) can be isolated, for example, by subjecting it to a post-treatment operation described below.
  • reaction mixture is added to water or acidic water such as hydrochloric acid, extracted with an organic solvent, and the organic layer is dried and concentrated.
  • acidic water such as hydrochloric acid
  • compound (49) and compound (50) can be produced by the following method.
  • L 11 and L 13 are the same or different and represent an alkoxy group such as a methoxy group, and RRRR 4 , R 5 , R 9 , R lfl and X have the same meanings as described above. ]
  • Compound (49) can be produced by reacting compound (48) with compound (48-1) or compound (48-2).
  • the reaction is performed in the presence or absence of a solvent.
  • Solvents used in the reaction include ethers such as 1,4-dioxane, tetrahydrofuran, ethylene glycol dimethyl ether, and t-butyl methyl ether; aliphatic hydrocarbons such as hexane and heptane; and aromatic hydrocarbons such as toluene.
  • ethers such as 1,4-dioxane, tetrahydrofuran, ethylene glycol dimethyl ether, and t-butyl methyl ether
  • aliphatic hydrocarbons such as hexane and heptane
  • aromatic hydrocarbons such as toluene.
  • Examples include hydrogens, hydrogenated hydrocarbons such as chlorobenzene, organic bases such as pyridine, triethylamine, N, N-dimethylaniline, N, N-dimethylformamide, and mixtures thereof.
  • the compound (48-1) or the compound (48-2) is usually in a ratio of 1 to 10 mol per 1 mol of the compound (48).
  • the reaction time is usually in the range of 1 to 24 hours, and the reaction temperature is usually in the range of 50 to 150.
  • the compound (49) can be isolated by performing post-treatment operations such as extraction of the reaction mixture with an organic solvent, and drying and concentration of the organic layer.
  • the isolated compound (49) can be further purified by chromatography, recrystallization, etc. it can.
  • Compound (27) can be produced by reacting compound (49) with water in the presence of an acid.
  • the reaction can be carried out using water as a solvent or in a mixture of water and another organic solvent.
  • compound (62) can be produced by the following method.
  • the reaction is usually carried out under a hydrogen atmosphere, usually in the presence of a solvent.
  • Examples of the solvent used in the reaction include alcohols such as methanol, ethanol, and propanol; esters such as ethyl acetate and butyl acetate; ethers such as tetrahydrofuran and 1,4-dioxane; and mixtures thereof.
  • Examples of the hydrogenation catalyst used for the reaction include transition metal compounds such as palladium carbon, palladium hydroxide, Raney nickel, and platinum oxide.
  • Examples of the acid used for the reaction include hydrochloric acid.
  • the reaction is usually performed under a hydrogen atmosphere at 1 to 100 atm.
  • the reaction temperature of the reaction is usually in the range of 120 to 100 ° C, and the reaction time is usually in the range of 0.1 to 24 hours.
  • Solvents used in the reaction include ethers such as 1,4-dioxane, tetrahydrofuran, ethylene glycol dimethyl ether and tert-butyl methyl ether; aliphatic hydrocarbons such as hexane, heptane and octane; toluene and xylene Aromatic hydrocarbons such as benzene, halogenated hydrocarbons such as chlorobenzene, esters such as butyl acetate and ethyl acetate, nitriles such as acetonitrile, acid amides such as N, N-dimethylformamide, Sulfoxides such as dimethyl sulfoxide and mixtures thereof.
  • ethers such as 1,4-dioxane, tetrahydrofuran, ethylene glycol dimethyl ether and tert-butyl methyl ether
  • aliphatic hydrocarbons such as hexane, heptane
  • the reaction is usually performed under a hydrogen atmosphere at 1 to 100 atm.
  • the reaction temperature of the reaction is usually in the range of 20 to 100 ° C, and the reaction time is usually in the range of 0.1 to 24 hours.
  • Solvents used in the reaction include ethers such as 1,4-dioxane, tetrahydrofuran, ethylene glycol dimethyl ether and tert-butyl methyl ether; aliphatic hydrocarbons such as hexane, heptane and octane; toluene; Aromatic hydrocarbons such as xylene, halogenated hydrocarbons such as chlorobenzene, esters such as butyl acetate and ethyl acetate, nitriles such as acetonitrile, acid amides such as N, N-dimethylformamide, Sulfoxides such as dimethyl sulfoxide and mixtures thereof.
  • ethers such as 1,4-dioxane, tetrahydrofuran, ethylene glycol dimethyl ether and tert-butyl methyl ether
  • aliphatic hydrocarbons such as hexane, heptane and oc
  • the reaction time is usually in the range of 0.5 to 24 hours, and the reaction temperature is usually in the range of 0 to 120 ° C.
  • the reaction is usually performed in the presence of a solvent.
  • Examples of the solvent used in the reaction include alcohols such as methanol and ethanol, ethers such as 1,4-dioxane, and mixtures thereof.
  • the reaction time is usually in the range of 1 to 24 hours, and the reaction temperature is usually in the range of 20 to 100 hours.
  • the reaction time is usually in the range of 1 to 24 hours, and the reaction temperature is usually in the range of 20 to 100.
  • the base is usually in a ratio of 0.5 to 3 mol per 1 mol of the compound (37).
  • the theoretical amount of oxygen is 1 mole for 1 mole of the compound (37).
  • the reaction time is usually in the range of 1 to 24 hours, and the reaction temperature is usually in the range of 20 to Ot.
  • L 1 represents a chlorine atom or a bromine atom
  • RRR 3 , R 4 , 5 and Q have the same meanings as described above.
  • the reaction is usually performed in the presence or absence of a solvent.
  • solvent used for the reaction examples include aromatic hydrocarbons such as toluene and xylene.
  • the amount of the halogenating agent is usually 1 to 5 mol per 1 mol of the compound (39).
  • the reaction time is usually in the range of 0.5 to 24 hours, and the reaction temperature is usually in the range of 50 to 120.
  • compound (2) After completion of the reaction, compound (2) can be isolated by performing post-treatment operations such as concentration of the reaction mixture.
  • Compound (39) can be prepared by the method described in International Patent Publication WOO 1/95721, International Patent Publication WO00 / 41998, International Patent Publication WO 96/23763, or International Patent Publication WO 96 31464. It can be manufactured according to. Further, among the compounds (39), the compound (45) can be produced according to (Intermediate production method 4).
  • R 22 represents a methyl group, Echiru group.
  • Compound (41) can be produced by reacting compound (40) with a reducing agent.
  • the reaction is usually performed in the presence of a solvent.
  • the reducing agent used in the reaction include sodium borohydride or potassium borohydride.
  • Solvents used in the reaction include methanol, ethanol, 2-propanol Alcohols such as 1,4-dioxane, tetrahydrofuran, ethylene glycol dimethyl ether, tert-butyl methyl ether, aliphatic hydrocarbons such as hexane, heptane, octane, and aromatics such as toluene and xylene Group hydrocarbons, water and mixtures thereof.
  • the amount of the reducing agent used in the reaction is usually 0.25 to 3 mol per 1 mol of the compound (40).
  • the reaction time is usually in the range of instant to 24 hours, and the reaction temperature is usually in the range of ⁇ 20 to 100 ° C.
  • the compound (41) can be isolated by performing post-treatment operations such as extracting the reaction mixture with an organic solvent and drying and concentrating the obtained organic layer.
  • the isolated compound (41) can be further purified by chromatography, recrystallization, or the like.
  • Compound (42) can be produced by reacting compound (41) with an alkylsulfonyl chloride compound.
  • reaction is carried out in the presence or absence of a solvent, usually in the presence of a base.
  • Solvents used in the reaction include ethers such as 1,4-dioxane, tetrahydrofuran, ethylene dimethyl dimethyl ether, and tert-butyl methyl ether; aliphatic hydrocarbons such as hexane, heptane and octane; toluene; Aromatic hydrocarbons such as silene, halogenated hydrocarbons such as chlorobenzene, esters such as butyl acetate and ethyl acetate, nitriles such as acetonitrile, acid amides such as N, N-dimethylformamide, dimethyl Sulfoxides such as sulfoxide and mixtures thereof.
  • ethers such as 1,4-dioxane, tetrahydrofuran, ethylene dimethyl dimethyl ether, and tert-butyl methyl ether
  • aliphatic hydrocarbons such as hexane, heptane and oc
  • Examples of the base used in the reaction include carbonates such as sodium carbonate and carbonated carbonate, alkali metal hydrides such as sodium hydride, triethylamine, diisopropylethylamine, 1,8-diazapicyclo [5.4.0] indec-7. —Ene, 1,5-diazabicyclo [4.3.0] non— Tertiary amines such as 5-ene and nitrogen-containing aromatic compounds such as pyridine and 4-dimethylaminopyridine.
  • the amount of the alkylsulfonyl chloride compound is usually 1 to 3 mol, and the amount of the base is usually 1 to 10 mol, per 1 mol of the compound (41).
  • the reaction time is usually in the range of 1 to 24 hours, and the reaction temperature is usually in the range of ⁇ 20 to 100.
  • the compound (42) is isolated by performing post-treatment operations such as concentrating the reaction mixture, adding an organic solvent to the obtained residue, filtering this, and concentrating the filtrate. Can be.
  • Compound (44) can be produced by reacting compound (42) with compound (15).
  • Solvents used in the reaction include ethers such as 1,4-dioxane, tetrahydrofuran, ethylene glycol dimethyl ether and tert-butyl methyl ether; aliphatic hydrocarbons such as hexane, heptane and octane; toluene and xylene Aromatic hydrocarbons such as benzene, halogenated hydrocarbons such as benzene, ester such as butyl acetate and ethyl acetate, nitriles such as acetonitrile, acid amides such as N, N-dimethylformamide, dimethyl sulfoxide And the like, and mixtures thereof.
  • ethers such as 1,4-dioxane, tetrahydrofuran, ethylene glycol dimethyl ether and tert-butyl methyl ether
  • aliphatic hydrocarbons such as hexane, heptane and o
  • Examples of the base used in the reaction include carbonates such as sodium carbonate and carbon dioxide, alkali metal hydrides such as sodium hydride, triethylamine, diisopropylethylamine, 1,8-diazabicyclo [5.4.0] indeck_7. —Ene, 1,5-diazabicyclo [4.3.0] non— Tertiary amines such as 5-ene and nitrogen-containing aromatic compounds such as pyridine and 4-dimethylaminopyridine.
  • the compound (15) is usually in a proportion of 1 mol to excess, and the base is usually in a proportion of catalyst to 5 mol, per 1 mol of the compound (42).
  • the reaction time is usually in the range of 1 to 24 hours, and the reaction temperature is usually in the range of 50 to 150.
  • the compound (44) can be isolated, for example, by subjecting it to a post-treatment operation described below.
  • Compound (45) can be produced by subjecting compound (44) to a hydrolysis reaction in the presence of a base.
  • the reaction is usually carried out in a solvent such as a mixture of water and an alcohol such as methanol or ethanol or an ether such as tetrahydrofuran or 1,4-dioxane.
  • a solvent such as a mixture of water and an alcohol such as methanol or ethanol or an ether such as tetrahydrofuran or 1,4-dioxane.
  • the base used in the reaction include alkali metal hydroxides such as lithium hydroxide, potassium hydroxide, and sodium hydroxide.
  • the base is usually in a proportion of 1 to 20 mol per 1 mol of the compound (44).
  • the reaction time is usually in the range of 0.5 to 24 hours, and the reaction temperature is usually in the range of 0 to 120 ° C.
  • the reaction mixture was acidified with an acid such as hydrochloric acid, extracted with an organic solvent, and the resulting organic layer was subjected to post-treatment operations such as drying and concentration, whereby the compound (45) was isolated. Can be released.
  • the isolated compound (45) can be further purified by operations such as chromatography and recrystallization.
  • Compound (51) can be produced by reacting compound (50) with an octaform form compound in the presence of a base in the presence of methanol.
  • haloform compound used in the reaction examples include black form, promoform, and rhodoform.
  • Examples of the base used in the reaction include alkali metal hydroxides such as sodium hydroxide and potassium hydroxide.
  • the base is usually in a proportion of 1 to 5 mol
  • the octaform compound is usually in a proportion of 1 to 5 mol, per 1 mol of the compound (50).
  • the reaction time is usually in the range of 1 to 24 hours, and the reaction temperature is usually in the range of 20 to 50 hours.
  • reaction mixture is acidified by adding diluted hydrochloric acid or the like, and then subjected to a post-treatment operation such as extraction with an organic solvent and drying and concentration of the obtained organic layer, thereby isolating the compound (51). can do.
  • the isolated compound (51) can be further purified by chromatography, recrystallization, or the like.
  • R 1 , R 2 , R 3 , R 4 , R 5 , R 21 and R 22 represent the same meaning as described above, and L 4 represents a chlorine atom, a bromine atom, an iodine atom or a methanesulfonyl group. . ]
  • Compound (54) can be produced by reacting compound (52) with compound (53) in the presence of a base.
  • the reaction is usually performed in the presence of a solvent.
  • solvent used in the reaction examples include aliphatic hydrocarbons such as hexane and pentane, halogenated hydrocarbons such as dichloromethane and dichloroethane, ethers such as tetrahydrofuran and getyl ether, and N, N-dimethylformamide and the like.
  • aliphatic hydrocarbons such as hexane and pentane
  • halogenated hydrocarbons such as dichloromethane and dichloroethane
  • ethers such as tetrahydrofuran and getyl ether
  • N, N-dimethylformamide and the like examples include acid amides and the like and mixtures thereof.
  • Examples of the base used in the reaction include alkali metal hydroxides such as sodium hydroxide and potassium hydroxide, alkali metal hydrides such as sodium hydride and potassium hydride, sodium methoxide, sodium ethoxide, and potassium t-oxide.
  • Metal alcoholates such as butoxide and lithium diisopropylamide.
  • the proportion of the base is usually 1 to 5 mol, and the proportion of the compound (53) is usually 0.5 to 1.2 mol, per 1 mol of the compound (52).
  • the reaction time is usually in the range of instant to 24 hours, and the reaction temperature is usually in the range of -20 to 100 ° C.
  • the reaction mixture is acidified by adding dilute hydrochloric acid or the like, then extracted with an organic solvent, and the obtained organic layer is subjected to post-treatment operations such as drying and concentration to isolate compound (54). can do.
  • the isolated compound (54) can be further purified by operations such as chromatography and recrystallization.
  • Compound (55) can be produced by subjecting compound (54) to a hydrolysis reaction in the presence of a base.
  • the reaction is usually carried out with water and alcohols such as methanol and ethanol or tetrahydric alcohol.
  • the reaction is performed in a solvent such as a mixture with ethers such as furan and 1,4-dioxane.
  • a solvent such as a mixture with ethers such as furan and 1,4-dioxane.
  • the base used in the reaction include alkali metal hydroxides such as lithium hydroxide and sodium hydroxide.
  • the base is usually in a proportion of 1 to 20 mol per 1 mol of the (54) compound represented by the formula.
  • the reaction time is usually in the range of 0.5 to 24 hours, and the reaction temperature is usually in the range of 0 to 120 ° C.
  • the reaction mixture was acidified with an acid such as hydrochloric acid and the like, and the resulting organic layer was subjected to post-treatments such as extraction with an organic solvent and drying and concentration of the obtained organic layer, whereby the compound (55) was isolated. Can be released.
  • the isolated compound (55) can be further purified by chromatography, recrystallization, or the like.
  • R 2 , R 3 , AA 2 , R 9 , R 1Q and X each represent a combination of the substituents shown in (Table 1).
  • R 2 , R 3 , A 3 , R 9 , R 1 () and X represent a combination of the substituents shown in (Table 2).
  • Examples of the plant disease having the controlling effect of the compound of the present invention include plant diseases caused by algae, and specific examples include the following diseases.
  • the plant disease controlling agent of the present invention may be the compound of the present invention itself, but is usually mixed with a solid carrier, a liquid carrier, a surfactant and other auxiliary agents for formulation to prepare an emulsion, a wettable powder, and a granule hydrate. It is formulated as a powder, flowable, powder, granule, etc. These preparations usually contain the present compound in an amount of 0.1 to 90% by weight.
  • the amount of treatment depends on the type of crop, etc., which is the plant to be controlled, the type of disease to be controlled, although it can be varied depending on the occurrence degree of the disease to be controlled, formulation, treatment time, weather conditions, etc.
  • the compound of the present invention is usually l to 500 g per 100 m 2 , preferably 5 to L 0. 0 g.
  • the method for controlling plant diseases of the present invention generally comprises applying an effective amount of the agent for controlling plant diseases of the present invention to a plant in which the occurrence of a disease is predicted or soil in which the plant grows, and confirming the occurrence of Z or the disease. It is carried out by treating the treated plant or the soil where the plant grows.
  • the plant disease controlling agent of the present invention is usually a plant disease controlling agent for agricultural and horticultural use, i.e., a plant disease controlling agent for controlling plant diseases such as fields, paddy fields, orchards, tea fields, pastures, lawns, etc. Used as
  • N- ⁇ 2- (3,4-dimethoxyphenyl) -12H-pyrazole-3-yl was prepared in the same manner as in Production Example 12 except that 4-trifluoromethylbenzaldehyde was used instead of 4-methylbenzaldehyde.
  • ⁇ _2-Methoxy-12- (4-trifluoromethylphenyl) acetamide (hereinafter, referred to as the present compound (1-23)) was obtained.
  • 2- (4-Methylphenyl) -2- (2-butynyloxy) acetamide (hereinafter referred to as the present compound (1-35)) was obtained.
  • solid is washed with hexane and dried, and N— ⁇ 2- (3,4-dimethoxyphenyl) —2H-pyrazol-3-yl ⁇ —2-hydroxy-21- (4-ethylphenyl) acetamide (hereinafter, referred to as “solid”) is used.
  • Compound of the present invention (referred to as 1-41) 1.2 g was obtained.
  • acetamide N- ⁇ 2- (3,4-dimethoxyphenyl) —2H-pyrazol-1-yl ⁇ -1- (4-acetylphenyl) acetamide (hereinafter referred to as “acetamide”)
  • acetamide N- ⁇ 2- (3,4-dimethoxyphenyl) —2H-pyrazol-1-yl ⁇ -1- (4-acetylphenyl) acetamide
  • Ethyl acetate was added to the reaction mixture, and liquid separation was performed to obtain an organic layer and an aqueous layer, respectively.
  • the obtained organic layer was washed with a 10% aqueous solution of sodium hydroxide, and the obtained aqueous layer was adjusted to near neutrality with carbon dioxide lime, and then extracted with ethyl acetate.
  • the obtained organic layers were mixed, washed sequentially with water and saturated saline, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure to obtain 6.14 g of crude 4-benzyloxy-3-methoxyphenylhydrazine.
  • 5-Amino-1_ (4-benzyloxy-1-methoxyphenyl) pyrazole-14-Ethyl rubonate 2.12 g and 10% aqueous sodium hydroxide solution 12 ml are mixed with ethanol 25 ml and heated under reflux 1.5. Stirred for hours. The reaction mixture was allowed to cool to room temperature, acidified by adding dilute hydrochloric acid, and concentrated under reduced pressure. The residue is filtered off, the solid obtained is washed with water, t-butyl methyl ether, dried and 5-amino-1- (4-benzyloxy-3-methoxyphenyl) -pyrazole-14- 1.50 g of carboxylic acid were obtained.
  • N- ⁇ 1- (4-Hydroxy-1-methoxyphenyl) pyrazole-5-yl ⁇ -2- (4-chlorophenyl) acetamide 224mg, 94mg of Propargyl, and 109mg of potassium carbonate were mixed with 6ml of acetonitrile. The mixture was stirred with heating under reflux for 3 hours. After allowing the reaction mixture to cool to room temperature, water was added, and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure.
  • a solution of 2-promonaphthalene in tetrahydrofuran (a mixed solution of 7.0 g of 2-promonaphthalene and 22 ml of tetrahydrofuran) was added dropwise to 0.86 g of magnesium at room temperature, and the mixture was stirred for 30 minutes. The mixture was cooled to 170 ° C., and a mixture of 9.9 g of diethyl oxalate and tetrahydrofuran was gradually added dropwise. The mixture was warmed to room temperature over 2 hours, saturated aqueous ammonium chloride was added, and the mixture was extracted with ethyl acetate.
  • Each of 50 parts of each of the compounds (1-1) to (1-60) of the present invention, 3 parts of lignin sulfonic acid potassium, 2 parts of magnesium lauryl sulfate, and 45 parts of synthetic hydrous silicon oxide are thoroughly ground and mixed. Obtain wettable powder.
  • Each powder is obtained by thoroughly pulverizing and mixing 2 parts of each of the compounds of the present invention (1-1) to (1-60), 88 parts of Olinclay and 10 parts of talc.
  • Test Examples show that the compounds of the present invention are useful for controlling plant diseases.
  • the control effect was evaluated by visually observing the area of the lesion on the test plant at the time of the survey, and comparing the area of the lesion in the untreated section with the area of the lesion in the section treated with the compound of the present invention.
  • the compounds of the present invention (I-1), (1-2), (1-4), (1-5), (I-7), (1-8), (1-11) to (1-11) 18), (1 -20) to (I-28), (I-30), (1-31), (I-35) to (I-38), (I-40) to (: 1-42) , (I-46) to (1-57) and (I-60) showed less than 10% of the lesion area on the plant in the untreated plot.
  • the area of the lesion on the treated plant was 76 to 100% of the area of the lesion in the untreated plot.
  • Plastic pots were filled with sandy loam, seeded with tomatoes (variety: Ponterosa), and grown in a greenhouse for 20 days.
  • Compounds (1-9), (1-29) and (1-32) of the present invention were made into flowable preparations according to Preparation Example 6, and then diluted with water to a predetermined concentration (200 ppm). The foliage was sprayed so as to sufficiently adhere to the leaves. After spraying, air-dry the diluted solution on the leaf surface to dryness, and spray inoculation with a suspension of zoospores of tomato epidemic (containing about 10,000 zoospores per lm of suspension) (plant About 2 ml per individual).
  • Plastic pots were filled with sandy loam, and tomatoes (variety: Bon terror) were sowed and grown in a greenhouse for 20 days.
  • the compound of the present invention (1-19) was made into a Floatable formulation in accordance with Formulation Example 6, then diluted with water to a predetermined concentration (50 ppm), and the diluted solution was sprayed on the foliage so that it would adhere sufficiently to the tomato leaf surface. did. After spraying, air-dry to the extent that the diluted solution on the leaf surface dries, and spray inoculation with a suspension of zoospores of tomato late blight (containing about 10,000 zoospores per ml of suspension) (plant 1) About 2 ml per individual).
  • the plants were cultivated for 1 day under the conditions of 23 ° C and a relative humidity of 90% or more, and then cultivated in a greenhouse at 24 ° C during the day and 20 ° C at night for 4 days. After that, the control effect was investigated. As a result, the lesion area on the plant to which the compound (I-119) of the present invention was tested was 10% or less of the lesion area of the untreated plot.
  • Plastic pots were filled with sandy loam, sown with grapes (variety: Berry A), and grown in a greenhouse for 40 days.
  • Compound of the present invention (1-1), (1-4), (1-8), (I-19), (1-12), (1-13), (1-15), (1-21) ⁇ (1-25), (I-28), (I-31), (I-32), (I-40), (I42), (1-46), (I-48), (1- 50), (1-51), (1-57), and (1-60) were made into a flowable formulation according to Formulation Example 6, then diluted with water to a predetermined concentration (200 ppm), and the diluted solution was added to grapes. The foliage was sprayed so as to sufficiently adhere to the leaves.
  • the compounds of the present invention (1-1), (1-4), (1-8), (I-19), (I-12), (1-13), (1-15), (I I 21)-(1-25), (I-28), (I-31), (1-32), (1-40), (1-42), (1-46), (I-48) ), (I
  • plant diseases can be controlled.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

L'invention concerne un composé phénylpyrazole représenté par la formule (1), dans laquelle R1, R2, R3, R4 et R5 représentent chacun indépendamment hydrogène, halogéno, etc., R6 représente hydrogène ou alkyle C1-3, R9 et R10 représentent chacun indépendamment alcoxy C1-6, etc., X représente oxygène ou soufre, et Q est Q1 {-CR14(Z1R15)-, où Z1 représente oxygène ou soufre, R14 représente hydrogène ou alkyle C1-3, et R15 représente hydrogène, alkyle C1-6, etc.}, Q2 {-C(=Z2)-, où Z2 représente oxygène, etc.}, ou Q3 {-CHR21-, où R21 représente hydrogène, alkyle C1-4, etc.}. Ce composé est hautement actif dans la lutte contre les maladies végétales.
PCT/JP2003/016076 2002-12-25 2003-12-16 Compose phenylpyrazole et methode de lutte contre une maladie vegetale au moyen de ce dernier Ceased WO2004058724A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU2003289105A AU2003289105A1 (en) 2002-12-25 2003-12-16 Phenylpyrazole compound and method of controlling plant disease with the same

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
JP2002-374041 2002-12-25
JP2002374041 2002-12-25
JP2003321010 2003-09-12
JP2003-321010 2003-09-12

Publications (1)

Publication Number Publication Date
WO2004058724A1 true WO2004058724A1 (fr) 2004-07-15

Family

ID=32684226

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP2003/016076 Ceased WO2004058724A1 (fr) 2002-12-25 2003-12-16 Compose phenylpyrazole et methode de lutte contre une maladie vegetale au moyen de ce dernier

Country Status (2)

Country Link
AU (1) AU2003289105A1 (fr)
WO (1) WO2004058724A1 (fr)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7514439B2 (en) 2005-07-11 2009-04-07 Mitsubishi Tanabe Pharma Corporation Oxime derivative and preparations thereof
US7749999B2 (en) 2003-09-11 2010-07-06 Itherx Pharmaceuticals, Inc. Alpha-ketoamides and derivatives thereof
US7902248B2 (en) 2006-12-14 2011-03-08 Hoffmann-La Roche Inc. Oxime glucokinase activators
US8314247B2 (en) 2007-01-10 2012-11-20 Mitsubishi Tanabe Pharma Corporation Hydrazone derivative
CN109369471A (zh) * 2018-12-10 2019-02-22 石家庄度恩医药科技有限公司 一种光学活性R-4-氯-α-(3-三氟甲基苯氧基)苯乙酸的制备方法

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS63313773A (ja) * 1987-06-16 1988-12-21 Tokuyama Soda Co Ltd ピラゾ−ル化合物
JPH06503069A (ja) * 1990-12-13 1994-04-07 ビーエーエスエフ　アクチェンゲゼルシャフト 置換５−アミノピラゾール
EP0811615A1 (fr) * 1996-06-03 1997-12-10 Rhone-Poulenc Agrochimie 1-Aryle-5-((thio)amido alkyl substitué) pyrazoles et leur utilisation comme pesticides
JPH107509A (ja) * 1996-06-17 1998-01-13 Rhone Poulenc Agrochim 新規な農薬
JP2002220376A (ja) * 2000-07-25 2002-08-09 Sankyo Co Ltd ５−（ｍ−シアノベンジルアミノ）ピラゾール誘導体
JP2002525272A (ja) * 1998-08-26 2002-08-13 バイエル アクチェンゲゼルシャフト 微生物を防除するための、５−アミノ−ピラゾール誘導体の使用
JP2003286117A (ja) * 2002-01-23 2003-10-07 Sankyo Agro Kk ５−（ｍ−シアノベンジルアミノ）ピラゾール誘導体を含有する農薬

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS63313773A (ja) * 1987-06-16 1988-12-21 Tokuyama Soda Co Ltd ピラゾ−ル化合物
JPH06503069A (ja) * 1990-12-13 1994-04-07 ビーエーエスエフ　アクチェンゲゼルシャフト 置換５−アミノピラゾール
EP0811615A1 (fr) * 1996-06-03 1997-12-10 Rhone-Poulenc Agrochimie 1-Aryle-5-((thio)amido alkyl substitué) pyrazoles et leur utilisation comme pesticides
JPH107509A (ja) * 1996-06-17 1998-01-13 Rhone Poulenc Agrochim 新規な農薬
JP2002525272A (ja) * 1998-08-26 2002-08-13 バイエル アクチェンゲゼルシャフト 微生物を防除するための、５−アミノ−ピラゾール誘導体の使用
JP2002220376A (ja) * 2000-07-25 2002-08-09 Sankyo Co Ltd ５−（ｍ−シアノベンジルアミノ）ピラゾール誘導体
JP2003286117A (ja) * 2002-01-23 2003-10-07 Sankyo Agro Kk ５−（ｍ−シアノベンジルアミノ）ピラゾール誘導体を含有する農薬

Non-Patent Citations (5)

* Cited by examiner, † Cited by third party
Title
DATABASE CAPLUS [online] ALBERTI C., TIRONI C.: "Pyrazole sulfanilamides", XP002976310, accession no. STN Database accession no. 1964:432385 *
DATABASE CAPLUS [online] PRAKASH A., GAMBHIR I.R.: "Substituted 2-sulfanilamido-azoacetoacetates and their cyclization", XP002976311, accession no. STN Database accession no. 1964:432386 *
FARMACO, EDITIONE SCIENTIFICA, vol. 19, no. 5, 1964, pages 459 - 473 *
J. INDIAN CHEMICAL SOCIETY, vol. 41, no. 3, 1964, pages 229 - 230 *
REGAN J. ET AL.: "Pyrazole urea-based inhibitors of p38 MAP kinase: from lead compound to clinical candidate", J. MED. CHEM., vol. 45, no. 14, 2002, pages 2994 - 3008, XP002243050 *

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7749999B2 (en) 2003-09-11 2010-07-06 Itherx Pharmaceuticals, Inc. Alpha-ketoamides and derivatives thereof
US7897599B2 (en) 2003-09-11 2011-03-01 iTherX Pharmaceuticals Inc. Cytokine inhibitors
US7919617B2 (en) 2003-09-11 2011-04-05 iTherX Pharmaceuticals Inc. Cytokine inhibitors
US7514439B2 (en) 2005-07-11 2009-04-07 Mitsubishi Tanabe Pharma Corporation Oxime derivative and preparations thereof
US8119626B2 (en) 2005-07-11 2012-02-21 Mitsubishi Tanabe Pharma Corporation Oxime derivative and preparations thereof
US7902248B2 (en) 2006-12-14 2011-03-08 Hoffmann-La Roche Inc. Oxime glucokinase activators
US8314247B2 (en) 2007-01-10 2012-11-20 Mitsubishi Tanabe Pharma Corporation Hydrazone derivative
CN109369471A (zh) * 2018-12-10 2019-02-22 石家庄度恩医药科技有限公司 一种光学活性R-4-氯-α-(3-三氟甲基苯氧基)苯乙酸的制备方法

Also Published As

Publication number Publication date
AU2003289105A1 (en) 2004-07-22

Similar Documents

Publication Publication Date Title
CN106536517B (zh) 一种含异恶唑啉的脲嘧啶类化合物及其用途
CN103081916B (zh) 吡唑酰胺类化合物作为农用杀菌剂的用途
JP2004131392A (ja) テトラゾール化合物およびその用途
CN106467537A (zh) 一种取代的酰胺类化合物与用途
CA2051537A1 (fr) Sulfonamides
WO2004058724A1 (fr) Compose phenylpyrazole et methode de lutte contre une maladie vegetale au moyen de ce dernier
CA2027195A1 (fr) Derives de pyridine et leur emploi pour la repression de la vegetation indesirable
CN103087041B (zh) 含二芳醚的吡唑酰胺类化合物作为农用杀菌剂的用途
WO2004016594A1 (fr) Compose phenylpyridine et composition bactericide le contenant
EP1577290A1 (fr) Amide et procede de lutte contre les maladies des plantes au moyen de ce compose
JP2002520384A (ja) アリールビニルエーテル誘導体およびそれらの除草剤としての使用
JPH11140054A (ja) ２−ピリドン誘導体及び除草剤
JP2005104954A (ja) フェニルピラゾール化合物及びその植物病害防除用途
CN105777640B (zh) 一种吡唑环己二醇醚类化合物及其应用
WO1992007846A1 (fr) Derive d'acide picolinique, sa production, et herbicide
WO2005000796A1 (fr) Amides et procede de regulation de maladies vegetales au moyen de ceux-ci
JP2004137270A (ja) 新規除草剤、その使用方法、新規置換チエノピリミジン誘導体及びその中間体並びにそれらの製造方法
JP2004137254A (ja) フェニルピリジン化合物及びそれを用いる植物病害防除方法
CN118221605A (zh) 一类含异噁唑啉类化合物、其制备方法及应用
JP2006008545A (ja) α−（Ｎ−アミド）ベンジルニトリル化合物ならびにその用途
JPH10500961A (ja) 複素環式イミノ誘導体
WO2005068416A1 (fr) Compose d'amide et methode de lutte contre des maladies des plantes au moyen de ce compose
CN115232083A (zh) 取代异噁唑乙胺类化合物及其制备方法和用途
WO2005122761A1 (fr) Composition bactéricide
JP2005314352A (ja) アミド化合物及びその用途

Legal Events

Date Code Title Description
AK Designated states

Kind code of ref document: A1

Designated state(s): AE AG AL AM AT AU AZ BA BB BG BR BW BY BZ CA CH CN CO CR CU CZ DE DK DM DZ EC EE EG ES FI GB GD GE GH GM HR HU ID IL IN IS KE KG KR KZ LC LK LR LS LT LU LV MA MD MG MK MN MW MX MZ NI NO NZ OM PG PH PL PT RO RU SC SD SE SG SK SL SY TJ TM TN TR TT TZ UA UG US UZ VC VN YU ZA ZM ZW

AL Designated countries for regional patents

Kind code of ref document: A1

Designated state(s): BW GH GM KE LS MW MZ SD SL SZ TZ UG ZM ZW AM AZ BY KG KZ MD RU TJ TM AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HU IE IT LU MC NL PT RO SE SI SK TR BF BJ CF CG CI CM GA GN GQ GW ML MR NE SN TD TG

121 Ep: the epo has been informed by wipo that ep was designated in this application
122 Ep: pct application non-entry in european phase