WO1995033730A1 - Derive d'imidazole, procede de production et herbicide - Google Patents

Derive d'imidazole, procede de production et herbicide Download PDF

Info

Publication number
WO1995033730A1
WO1995033730A1 PCT/JP1995/001149 JP9501149W WO9533730A1 WO 1995033730 A1 WO1995033730 A1 WO 1995033730A1 JP 9501149 W JP9501149 W JP 9501149W WO 9533730 A1 WO9533730 A1 WO 9533730A1
Authority
WO
WIPO (PCT)
Prior art keywords
group
substituted
optionally substituted
halogen atom
alkoxy
Prior art date
Application number
PCT/JP1995/001149
Other languages
English (en)
Japanese (ja)
Inventor
Kenji Hagiwara
Michiaki Maruyama
Hiroshi Suzuki
Takashi Kawana
Akihiro Takahashi
Shigeo Yamada
Original Assignee
Nippon Soda 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 Nippon Soda Co., Ltd. filed Critical Nippon Soda Co., Ltd.
Priority to AU26305/95A priority Critical patent/AU2630595A/en
Publication of WO1995033730A1 publication Critical patent/WO1995033730A1/fr

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/64—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms, e.g. histidine
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D233/68—Halogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • 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
    • C07D417/04—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 directly linked by a ring-member-to-ring-member bond

Definitions

  • the present invention relates to a novel imidazole derivative useful as a herbicide and a method for producing the same.
  • Background art :
  • EP-0 283 173 describes that certain imidazole derivatives are useful as insecticides and nematicides. However, it does not specifically disclose the compound relating to the present invention, nor does it disclose any usefulness as a herbicide.
  • the purpose of the present invention is to provide a herbicide that can be synthesized industrially advantageously, is effective at a lower dose, has high safety, and has high crop selectivity. Disclosure of the invention:
  • the present invention relates to an imidazole derivative represented by the general formula [I], a production method and a herbicide. You.
  • X is [halogen atom, (halogen atom, an optionally substituted Hue alkenyl group, C - e alkoxy group, d-6 alkoxycarbonyl group, Horumiruokishi group or Shiano group).
  • halogen atom an optionally substituted Hue alkenyl group, C - e alkoxy group, d-6 alkoxycarbonyl group, Horumiruokishi group or Shiano group
  • C alkyl group halogen atom, an optionally substituted Fuweniru group, alkoxy group, C alkoxycarbonyl group or Shiano group
  • C - e alkoxy group
  • d-alkylthio group C haloalkylthio group
  • 6 alkylsulfide alkylsulfonyl groups C] - alkyl sulfonyl groups, C Nono b alkylsulfonyl groups, C l-6 alkylsulfony
  • C alkoxycarbonyl group an optionally substituted C Bok 6 alkyl group with halogen, mono Moshiku (C, - - 6 alkyl group, C! 6 Ashiru group is properly alkoxy carbonyl group) depending disubstituted amino group, an optionally substituted phenyl group, an optionally substituted Fuwenokishi group or an optionally substituted pyridinium Jiruoki sheet group] which may be substituted with Fuweniru group, (halogen atom, C, - e alkyl group, Pyridyl group, pyridyl N-oxide group, alkyl group, halogen atom or oxo group) which may be substituted with 1 to 3 haloalkyl groups, alkoxy groups or cyano groups).
  • Y, Z has one represents a 6 haloalkyl group, the other is a hydrogen atom, halogen atom, C -! 6 alkyl group, a haloalkyl group, 6 alkylthio groups, C 1 -6 alkoxy group, Shiano group, a formyl group, human Dorokishii Mi Bruno methyl group, C 1 -6 Arukokishii Mi Nomechiru group, C -!
  • R represents [(halogen atom, C, —S alkoxy group, ds alkoxyalkoxy group, optionally substituted phenyl group, optionally substituted phenoxy group, C, -6 alkoxycarbonyl group, C 3 - 6 cycloalkyl group or Shiano group) which may be substituted with an alkoxy group, is substituted with (halogen, C -e alkoxy groups, unsubstituted or good I Fuweniru group, an alkoxycarbonyl group, or Shiano group)!
  • C 3 be - 6 Arukeniruokishi group, (halogen atom, C i-6 alkoxy group, an optionally substituted Fuweniru group, d-6 alkoxycarbonyl or Shiano group)
  • C 3 which may be substituted by - e
  • Arukiniruokishi group, (halogen atom, an alkoxy group, an optionally substituted Fuweniru group, C i-6 alkoxycarbonyl group or Shiano group) may be substituted with Ararukiru Alkoxy group, d-6 alkylcarbonyl O alkoxy group, (halogen atom, C -!
  • C I 6 may be substituted by alkylthio O group, alkylsulfinyl group, an alkylsulfonyl group, an Fuwenokishi group optionally substituted by a halogen atom, C i-6 alkyl group, ⁇ Mi substituted by (C iS alkyl group may properly C 6 alkoxycarbonyl group) It represents an 8 alkenyl group - amino group, d - 6 alkoxy force which may Fuweniru group or a C I is substituted with alkyl groups Lupo alkylsulfonyl group] optionally C i-6 alkyl group or optionally substituted by a C 3.
  • examples of the substituent for the phenyl-alkyl-phenyl group and the phenyl-alkoxy-phenyl group of X include a halogen atom, c
  • Examples of the substituent for X's biphenyl group, phenoxyphenyl group and pyridyloxyphenyl group include a halogen atom and d-6 haloalkyl group.
  • Examples of the condensed ring group of benzene and a 5- to 6-membered hetero ring containing 1 to 3 N, 0 or S of X include a condensed ring group of a heterocyclic ring and a phenyl group as shown below.
  • Examples include a fused ring group of benzene and a pyridyl group such as a quinolyl group.
  • substituents when the phenyl group, heterocycle or pyridyl group of X is substituted with two or more substituents, these substituents may be the same or different.
  • the compound of the present invention can be produced by the following method.
  • Solvents that can be used in the reaction include hydrocarbons such as hexane, heptane, benzene, toluene, and xylene; ethers such as THF, dioxane, and getyl ether; methanol, ethanol, and propanol. Alcohols, amides such as DMF and DMS O, halogenated solvents such as chloroform, dichloromethane, carbon tetrachloride, and dichloroethane; esters and esters such as ethyl acetate, methyl acetate, and propyl acetate. Cetonitrile and the like.
  • Examples of the base used in the reaction include aliphatic amines such as triethylamine, getylisopropylamine and piperidine, aromatic amines such as pyridine and aniline, and sodium carbonate.
  • Alkali metal carbonates such as calcium carbonate, calcium carbonate, etc.
  • metal alkoxides such as calcium methoxide, sodium ethoxide, magnesium ethoxide, calcium tert-butoxide, etc.
  • Al metal hydroxides such as tritium and hydroxide hydroxide, metal hydrides such as sodium hydride and the like can be mentioned.
  • the compound (II) can be synthesized, for example, according to the production method described in U.S.P. 4,314,844. Manufacturing method (2)
  • Y is a haloalkyl group
  • Z is a chlorine atom, a fluorine atom, a substituted benzoyl group, a cyano group, a formyl group, a hydroxyiminomethyl group, an alkoxyminomethyl group, and an alkoxyl group.
  • Those having a carbonyl group, a trifluoromethyl group, an alkylthio group or a carboxy group can be produced by the following method.
  • V represents an iodine atom or a bromine atom
  • R 1 , R 2 , R 4 , and R 5 represent an alkyl group of 6
  • R 3 Represents a hydrogen atom or a d- 6 alkyl group
  • R 6 represents a halogen atom.
  • N represents an integer of 0-5.
  • the compound of the present invention can also be obtained by the following production method.
  • the compound [ ⁇ ] which is a starting material of a compound in which Y is a CF 3 group and Z is a C! -S alkyl group, can be produced by the following method.
  • a compound in which Y is a CF 3 group and Z is a substituted phenyl group can be produced by the following method.
  • C represents a -5 alkyl group.
  • the compound of the present invention shows high efficacy against various field weeds such as mexican grass, Aquinoeno cologsa and Inubu by any of soil treatment and foliage treatment under upland cropping conditions, and particularly shows excellent efficacy in upland soil treatment.
  • the compounds of the present invention include compounds having selectivity for crops such as corn, wheat, and soybeans.
  • the compound of the present invention has excellent herbicidal activity against weeds such as paddy field weeds such as Nobie, Tamagayari, Omodaka and Firefly, and also includes compounds showing selectivity to rice.
  • weeds such as paddy field weeds such as Nobie, Tamagayari, Omodaka and Firefly
  • the compounds of the present invention can also be applied to the control of weeds in orchards, lawns, track ends, vacant lots and the like.
  • the compounds of the present invention include those having a plant growth regulating action, a bactericidal activity, and an insecticidal / miticidal activity.
  • the herbicide of the present invention contains one or more of the compounds of the present invention as an active ingredient.
  • the compound of the present invention can be used in a pure form without adding other components, and can be in the form of a general pesticide for use as a pesticide, that is, a wettable powder, a granule, It can also be used in the form of powders, emulsions, aqueous solvents, suspensions, flowables and the like.
  • plant-based powders such as soy flour and flour, diatomaceous earth, apatite, gypsum, talc, bentonite, pyrophyllite, clay, etc.
  • Organic and inorganic compounds such as fine powder, sodium benzoate, urea and sodium sulfate are used.
  • petroleum fractions such as kerosene, xylene and sorbent naphtha, cyclohexane, cyclohexanone, dimethylformamide, dimethylsulfoxide, alcohol, acetate , Trichloroethylene, methyl isoptil ketone, mineral oil, vegetable oil, water, etc. are used as solvents.
  • Surfactants can be added, if necessary, to obtain a uniform and stable form in these preparations.
  • the concentration of the active ingredient in the herbicide of the present invention varies depending on the form of the preparation described above.
  • a wettable powder it is 5 to 90%, preferably 10 to 8%. 5%: 3 to 70% in emulsion, preferably 5 to 30%: 0.01 to 30% in granules, preferably 0.05 to 5% A concentration of 10% is used.
  • the wettable powder and emulsion thus obtained are diluted to a predetermined concentration with water to form a suspension or emulsion, and the granules are sprayed on the soil before or after germination of the weeds. Or it is mixed.
  • an appropriate amount of 0.1 g or more of the active ingredient is applied per 10 ares.
  • the herbicide of the present invention can be used by mixing with known fungicides, insecticides, acaricides, herbicides, plant growth regulators, fertilizers and the like.
  • the synergistic action of the mixed drug can be expected to have a higher effect. In that case, a combination with a plurality of known herbicides is also possible.
  • agents that can be used in combination with the herbicide of the present invention include carbamate herbicides such as benthiocarb, molinate, and dime pipelet; tiocarbamate herbicides; butachlor; pretilachlor; Acid amide herbicides, such as chlormethoxinil, biphenox, etc .; triazine herbicides, such as atrazine and dianadine; sulfonylurea herbicides, such as chlorsulfuron and sulfometuron-methyl.
  • Carboxylic herbicides such as MCP and MCPB, dinitroaniline herbicides such as trifluralin and benzimetalin, urea herbicides such as linuron and diuron, and diclohop-methyl.
  • Phenoxy phenoxypropionic herbicide, flazifop Pyridyloxyphenoxypropionic acid herbicides such as tyl
  • benzoylaminopropionic acid herbicides such as benzoylprophetyl and franpropethyl
  • imazaquin imidazolinone herbicides and others
  • cyclohexanedione herbicides such as pilophos, Daimlon, Benyuzon, difenzocoat, nabroanilide, etobenzanide, triazovanamide, kink mouth rack, and cetoxidim, cresodim. And the like.
  • Vegetable oils and oil concentrates can also be added to these combinations.
  • Example 4 wettable powder
  • the above components were uniformly mixed and finely pulverized to obtain a wettable powder containing 20% of the active ingredient.
  • the herbicidal effect was investigated according to the following criteria and expressed as a herbicidal index.
  • Numerical values of 1, 3, 5, 7, and 9 indicate intermediate values between 0 and 2, 2 and 4, 4 and 6, 6 and 8, and 8 and 10, respectively.
  • Herbicidal rate (%) X100
  • Test example 1 Upland soil treatment
  • a plastic pot having a surface area of 250 cm 2 was filled with field soil, and seeds of Meechishiba, Aquinoeno coroda and Inubu were sown, and a 0.5 cm cover soil was placed thereon. The following day, a predetermined amount of the diluent of the wettable powder shown in Example 4 was evenly sprayed on the soil surface. Twenty days after the treatment, the herbicidal effect was investigated. The results are shown in Table 2.
  • the imidazole derivative compound of the present invention represented by the formula [I] was shown to have excellent herbicidal activity in a soil treatment test. Therefore, the compound of the present invention is useful as a herbicide.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

Dérivé d'imidazole représenté par la formule générale (I), présentant une excellente action herbicide lorsqu'on l'utilise notamment pour le traitement des sols. Dans la formule, X représente phényle qui peut être substitué par halogène, alkyle C1-C6 éventuellement substitué, alcoxy C1-C6, alkylthio C1-C6, nitro, cyano, alcoxycarbonyle C1-C6 ou d'autres substituants, pyridyle qui peut être substitué, etc.; un composé parmi Y et Z représente haloalkyle C1-C6 et l'autre représente hydrogène, halogène, alkyle C1-C6, etc.; et R représente alkyle C1-C6 qui peut être substitué par alcoxy C1-C6 éventuellement substitué, alcényloxy C3-C6 éventuellement substitué, alkynyloxy C3-C6 éventuellement substitué, aralkyloxy éventuellement substitué, etc.
PCT/JP1995/001149 1994-06-09 1995-06-08 Derive d'imidazole, procede de production et herbicide WO1995033730A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU26305/95A AU2630595A (en) 1994-06-09 1995-06-08 Imidazole derivative, production process, and herbicide

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
JP15172194 1994-06-09
JP6/151721 1994-06-09
JP6872595 1995-03-02
JP7/68725 1995-03-02

Publications (1)

Publication Number Publication Date
WO1995033730A1 true WO1995033730A1 (fr) 1995-12-14

Family

ID=26409925

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP1995/001149 WO1995033730A1 (fr) 1994-06-09 1995-06-08 Derive d'imidazole, procede de production et herbicide

Country Status (2)

Country Link
AU (1) AU2630595A (fr)
WO (1) WO1995033730A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN108430976A (zh) * 2015-12-16 2018-08-21 日本曹达株式会社 芳基唑化合物和有害生物防除剂

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4125530A (en) * 1969-12-15 1978-11-14 Merck & Co., Inc. Trifluoromethylimidazoles and a method for their preparation
JPS54148788A (en) * 1978-05-15 1979-11-21 Takeda Chem Ind Ltd 1,2-disubstituted-4-halogenoimidazole-5-acetic acid derivative and its preparation
JPS5545695A (en) * 1978-09-28 1980-03-31 Bayer Ag Nn*1*33azolyl**alkyl halogenoacetoanilide its manufacture and its use as herbicide
JPS6034951A (ja) * 1983-08-04 1985-02-22 Tanabe Seiyaku Co Ltd イミダゾール誘導体及びその製法
JPS63238065A (ja) * 1987-03-05 1988-10-04 ローヌ―プーラン・アグリカルチヤー・リミテツド ２‐フェニルイミダゾール誘導体を用いる殺虫方法
JPH03101669A (ja) * 1989-06-06 1991-04-26 Roussel Uclaf 新規なチアゾリルアルコキシアクリル酸エステル、それらの製造法、それらの殺菌剤としての使用及びそれらの製造中間体

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4125530A (en) * 1969-12-15 1978-11-14 Merck & Co., Inc. Trifluoromethylimidazoles and a method for their preparation
JPS54148788A (en) * 1978-05-15 1979-11-21 Takeda Chem Ind Ltd 1,2-disubstituted-4-halogenoimidazole-5-acetic acid derivative and its preparation
JPS5545695A (en) * 1978-09-28 1980-03-31 Bayer Ag Nn*1*33azolyl**alkyl halogenoacetoanilide its manufacture and its use as herbicide
JPS6034951A (ja) * 1983-08-04 1985-02-22 Tanabe Seiyaku Co Ltd イミダゾール誘導体及びその製法
JPS63238065A (ja) * 1987-03-05 1988-10-04 ローヌ―プーラン・アグリカルチヤー・リミテツド ２‐フェニルイミダゾール誘導体を用いる殺虫方法
JPH03101669A (ja) * 1989-06-06 1991-04-26 Roussel Uclaf 新規なチアゾリルアルコキシアクリル酸エステル、それらの製造法、それらの殺菌剤としての使用及びそれらの製造中間体

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN108430976A (zh) * 2015-12-16 2018-08-21 日本曹达株式会社 芳基唑化合物和有害生物防除剂
US20180362470A1 (en) * 2015-12-16 2018-12-20 Nippon Soda Co., Ltd. Arylazole compound and pest control agent
US11180456B2 (en) * 2015-12-16 2021-11-23 Nippon Soda Co., Ltd. Arylazole compound and pest control agent
CN108430976B (zh) * 2015-12-16 2022-07-05 日本曹达株式会社 芳基唑化合物和有害生物防除剂
US11884633B2 (en) 2015-12-16 2024-01-30 Nippon Soda Co., Ltd. Arylazole compound and pest control agent

Also Published As

Publication number Publication date
AU2630595A (en) 1996-01-04

Similar Documents

Publication Publication Date Title
JP3002786B2 (ja) 有害生物防除組成物
JPH05271207A (ja) 置換ニトログアニジン誘導体、その製造方法及び殺虫剤
JP2003064059A (ja) ピリミジン化合物、製造方法および除草剤
WO1996033994A1 (fr) Derives amino-substitues, leur procede de preparation et herbicide
DE3687021T2 (de) Pyridazinonderivate, verfahren zu deren herstellung und insekttoetende zusammenstellungen.
JP2921047B2 (ja) 置換ビシクロヘプタジオン誘導体、その製造方法及び除草剤
JPH0558979A (ja) ３，４−ジ（置換フエニル）酪酸誘導体および除草剤
BG97615A (bg) Нови фунгициди производни на триазола и имидазола
WO1995033730A1 (fr) Derive d'imidazole, procede de production et herbicide
JPS63159372A (ja) ピリダジノン化合物および殺虫、殺ダニ、殺線虫剤
JPH02233602A (ja) 除草剤
JPH03148265A (ja) ５，７―ジフェニル―４，６―ジアザインダン誘導体、その製造法およびそれを有効成分とする除草剤
JPH04211065A (ja) ３−置換フェニルピラゾール誘導体又はその塩類及びその用途
JPH0739397B2 (ja) ピリダジノン誘導体および害虫防除剤
JPH0253775A (ja) ピラゾールカルボキサミド誘導体及び除草剤
JP2714671B2 (ja) チアジアザビシクロノナン誘導体及び除草剤
JP3462247B2 (ja) カルボヒドロキシモイルアゾール誘導体及び殺虫剤
JPS6229433B2 (fr)
JPS61291573A (ja) ２−フエニル−４，５，６，７，−テトラヒドロ−２ｈ−インダゾ−ル誘導体、その製造方法、及び除草剤
JPH08198855A (ja) ピリダジノン誘導体および害虫防除剤
JP3283069B2 (ja) 置換アルケニルケトン誘導体及び殺虫剤
JPS63156779A (ja) ピリダジノン誘導体、その製造方法及び除草剤
JPH02726A (ja) シクロヘキセノン誘導体、その製造方法及び除草剤
JPH0338586A (ja) 置換ピリジン誘導体、その製造方法及び除草剤
JPH0193583A (ja) 置換ベンゾイル誘導体および除草剤

Legal Events

Date Code Title Description
AK Designated states

Kind code of ref document: A1

Designated state(s): AU BR CA CN HU JP KR RU UA US

AL Designated countries for regional patents

Kind code of ref document: A1

Designated state(s): AT BE CH DE DK ES FR GB GR IE IT LU MC NL PT SE

DFPE Request for preliminary examination filed prior to expiration of 19th month from priority date (pct application filed before 20040101)
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
122 Ep: pct application non-entry in european phase
NENP Non-entry into the national phase

Ref country code: CA