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EP0915873A1 - Derives de pyrazolyle-pyrazol substitues, procede permettant de les preparer et utilisation comme agents a effet herbicide - Google Patents

Derives de pyrazolyle-pyrazol substitues, procede permettant de les preparer et utilisation comme agents a effet herbicide

Info

Publication number
EP0915873A1
EP0915873A1 EP97937465A EP97937465A EP0915873A1 EP 0915873 A1 EP0915873 A1 EP 0915873A1 EP 97937465 A EP97937465 A EP 97937465A EP 97937465 A EP97937465 A EP 97937465A EP 0915873 A1 EP0915873 A1 EP 0915873A1
Authority
EP
European Patent Office
Prior art keywords
alkyl
hydrogen
substituted
general formula
halogen
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.)
Withdrawn
Application number
EP97937465A
Other languages
German (de)
English (en)
Inventor
Helga Franke
Uwe Hartfiel
Michael Granzer
Eberhard Richter
Jürgen Bohner
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.)
Bayer CropScience AG
Original Assignee
Hoechst Schering Agrevo GmbH
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 Hoechst Schering Agrevo GmbH filed Critical Hoechst Schering Agrevo GmbH
Publication of EP0915873A1 publication Critical patent/EP0915873A1/fr
Withdrawn legal-status Critical Current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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/04—Ortho-condensed systems
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
    • A01N43/42—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings condensed with carbocyclic rings
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—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
    • 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
    • A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
    • 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
    • C07D231/12—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 only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • 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
    • C07D233/56—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 only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles

Definitions

  • the invention relates to substituted pyrazolyl-pyrazole derivatives, their preparation and intermediates for their preparation and their use as agents with herbicidal activity
  • No. 5,405,829 discloses pyrazolyl-pyrazoles with an unsubstituted amino group as herbicidally active compounds
  • WO 94/03999 describes herbicidally active pyrazolyl-pyrazoles, inter alia with a substituted amino group
  • RC r C 4 alkyl C r C 4 -Alkylth ⁇ o, C r C 4 -Alkylsulf ⁇ nyl, C r C 4 alkylsulfonyl, C r C 4 - alkoxy, mono- or polysubstituted by halogen-substituted C r C alkyl, C r C 4 - alkylthio, C r C 4 alkylsulfonyl, C r C 4 alkylsulfonyl or C r C 4 alkoxy,
  • R 1 and R 2 together form the group - (CH 2 ) n -,
  • R 3 is hydrogen or halogen
  • R 4 is hydrogen or C r C 4 alkyl
  • R hydrogen, nitro, cyano, -COOR 7 , the group
  • R b is hydrogen, C r C 6 alkyl, C 3 -C 7 cycloalkyl, C3-C 7 cycloalkyl-C r C 4 alkyl, C 2 -C 6 alkenyl, C 3 -C 6 alkynyl or more times by halogen, hydroxy, cyano, C r C 4 alkoxy, C r C 4 -Alkth ⁇ o, C r C 4 alkoxy-carbonyl, hydroxycarbonyl, C 1 -C alkylcarbonyl substituted C 1 -C 6 alkyl, C 2 - C 6 - alkenyl, C 3 -C 6 alkynyl, one or more times interrupted by oxygen or sulfur C r C 8 alkyl, C 3 -C 7 cycloalkyl, C 3 -C 7 cycloalkyl-C r C 4 alkyl , where appropriate cycloalkyl can be substituted one or more times by methyl, phenyl
  • Preferred compounds of the formula I are those in which
  • R 1 is methyl
  • R 1 and R 2 together form the group - (CH 2 ) 4 -,
  • R 3 chlorine or bromine
  • R 4 is hydrogen
  • R 6 is hydrogen, C r C 6 alkyl, C 2 -C 6 alkenyl, C 3 -C 6 alkynyl, by cyano, C r C 4 -
  • alkyl stands for a straight or branched chain of carbon atoms
  • alkylene stands for a straight-line or branched chain of carbon atoms which is interrupted one or more times by double bonds
  • alkynyl stands for a straight-line or branched chain of carbon atoms which is interrupted once or several times by triple bonds
  • the compounds of general formula I according to the invention can be prepared by A) a compound of general formula II
  • R .1 1 , R ⁇ , R, R and R have the meanings given in the general formula I and R 6 is hydrogen, or
  • R 6 has the meanings given in the general formula I and Z represents a leaving group, or in the presence of a base C) a compound of the general formula
  • R - R have the meanings given in general formula I, reacted with a suitable formylating reagent, or
  • R 1 -R 3 have the meanings given in the general formula I, reacted with a suitable formylation reagent and then nitrated, or
  • R 2 is C 1 -C 4 -alkylsulfinyl, C 1 -C -alkylsulfonyl, one or more halogen-substituted CC 4 -alkylsulfinyl or C r C 4 -alkylsuifonyl, a compound of the general formula IIa
  • R 1, R 3, R 4 and R 5 have the meaning indicated in formula I and R 11 is C r C 4 alkyl or mono- or polysubstituted by halogen-substituted C r C alkyl, is reacted with an oxidizing agent
  • hydrogen peroxide perbenzoic acids, sodium pirene iodate or potassium permanganate
  • oxidizing agent hydrogen peroxide, perbenzoic acids, sodium pirene iodate or potassium permanganate
  • acetic acid formic anhydride or formic acid can be used as the formylating agent
  • concentrated nitric acid or mixtures of fuming nitric acid with concentrated sulfuric acid can be used as the nitrating agent
  • the reactions are expediently carried out in such a way that the compounds are reacted at temperatures between -30 and 150 ° C.
  • Bases which can be used are, for example, alkali and alkaline earth metal hydroxides, alkali and alkaline earth metal carbonates and hydrogen carbonates, alcoholates, alkali metal hydrides, tertiary aliphatic and aromatic amines, such as tetrahydromamine and py ⁇ din, and heterocyclic bases
  • Escape groups are, for example, bromine, chlorine or iodine
  • the compounds of the general formula IIa used as starting material can be prepared by compound of the general formulas V or VI
  • the compounds of general formula VII in which R 1 , R 2 , R 3 have the meaning given in general formula I and m is 1 or 2, can be prepared by reacting compounds of general formula VIII with an oxidizing agent
  • the compounds of the general formula VIII, in which R 1 and R 2 have the meanings given in the general formula I and R 3 is hydrogen, can be prepared by either a compound of the formula IX
  • the preparation can be carried out with or without solvents, the solvents mentioned above being used if necessary
  • hydrogen peroxide perbenzoic acids, sodium p ⁇ odate or potassium permanganate
  • oxidizing agent hydrogen peroxide, perbenzoic acids, sodium p ⁇ odate or potassium permanganate
  • halogenating agents examples include sulfuryl chloride, sodium hypochlorite, N-chlorosuccinimide, N-bromosuccinimide, bromine or chlorine
  • alkali and alkaline earth hydroxides for example, alkali and alkaline earth hydroxides, sodium methoxide, alkali hydrates, alkali and alkaline earth carbonate, tertiary aliphatic and aromatic amines, such as tetramethylamine and pyridine, and heterocyclic bases can be used.
  • the reactions are carried out at a temperature between -30 and 150 ° C. carried out
  • the compounds according to the invention are worked up in the customary manner. Purification is carried out by crystallization or column chromatography
  • the compounds according to the invention are generally colorless or pale yellow colored crystalline or viscous substances, some of which are readily soluble in chlorinated hydrocarbons such as methylene chloride or chloroform, ethers such as diethyl ether or tetrahydrofuran, alcohols such as methanol or Ethanol, ketones such as acetone or butanone, amides such as dimethylformamide or sulfoxides such as dimethyl sulfoxide.
  • the compounds according to the invention have a good herbicidal action on broad-leaved weeds and grasses.
  • a selective use is possible in different cultures, e.g. in rapeseed, beets, soybeans, cotton, rice, corn, barley, wheat and other types of goats.
  • Individual compounds are also suitable as selective herbicides in beets, cotton, soybeans, corn and cereals.
  • the compounds for weed control in permanent crops such as e.g. can be used in forestry, ornamental wood, fruit, wine, citrus, nut, banana, coffee, tea, rubber, oil palm, cocoa, berry fruit and hop plants.
  • the compounds of the invention can e.g. in the following
  • Plant genera are used.
  • Dicotyledon weeds of the genera such as Sinapsis, Lepidium, Galium, Stellaria,
  • Monocot weeds of the genera such as Avena, Alopecurus, Echinochloa, Setaria,
  • the application rates fluctuate between 0.001 and 5 kg / ha in the pre- and post-emergence.
  • the intensity and speed of action can be promoted, for example, by additives which increase the effectiveness, such as organic solvents, Wetting agents and oils can be achieved. Such additives may therefore allow the active ingredient dosage to be reduced
  • the active compounds according to the invention or mixtures thereof are expedient in the form of preparations such as powders, sprinkling agents, granules, solutions, emulsions or suspensions with the addition of liquid and / or solid carriers or diluents and, if appropriate, adhesives, wetting agents, emulsifiers and / or dispersants applied
  • Suitable liquid carriers are, for example, aliphatic and aromatic hydrocarbons, such as benzene, toluene, xylene, cyclohexanone, isophorone, dimethylsuloxide, dimethylformamide, mineral oil fractions and vegetable oils
  • Minerals such as bentonite, silica gel, talc, kaolin, attapulgite, limestone and vegetable products are suitable as solid carriers.
  • flours such as bentonite, silica gel, talc, kaolin, attapulgite, limestone and vegetable products are suitable as solid carriers.
  • flours such as bentonite, silica gel, talc, kaolin, attapulgite, limestone and vegetable products are suitable as solid carriers.
  • flours such as bentonite, silica gel, talc, kaolin, attapulgite, limestone and vegetable products are suitable as solid carriers.
  • flours such as bentonite, silica gel, talc, kaolin, attapulgite, limestone and vegetable products are suitable as solid carriers.
  • flours such as bentonite, silica gel, talc, kaolin, attapulgite, limestone and vegetable products are suitable as solid carriers.
  • flours such as bentonite, silica gel,
  • Examples of surface-active substances include calcium lignin sulfonate, polyethylene alkylphenyl ether, naphthane sulfonic acids and their salts, phenol sulfonic acids and their salts, formaldehyde condensates, fatty alcohol sulfates and substituted benzenesulfonic acids and their salts
  • the proportion of the active substance (s) in the various preparations can vary within wide limits.
  • the agents contain about 10 to 90% by weight of active ingredient, about 90 to 10% by weight of liquid or solid carriers and optionally up to 20% by weight.
  • the agents can be applied in a customary manner, for example using water as a carrier in spray boiling quantities of about 100 to 1000 liters / ha.
  • the agents can be used in the so-called low-volume and ultra-low-volume method, as can their application in the form of so-called microgranules
  • preparations can be prepared in a manner known per se, For example, by grinding or mixing processes. If desired, preparations of the individual components can also be mixed only shortly before they are used, as is carried out in practice in the so-called tank mixing process
  • reaction mixture was concentrated, the residue was added to an ice-cold solution of 290 g (2.1 mol) of potassium carbonate in 3 l of water with stirring for one hour stirred, the solid filtered off and washed twice with 2 l of water each time. The solid was dried at 50 ° C. (200 mbar) and then re-installed from methanol
  • Ph phenyl
  • the compounds listed in the table were applied by pipetting to a water surface of approximately 170 cm 2 , the test plants being used both in the pre-emergence and in the 1-3-leaf statium.

Landscapes

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

Abstract

L'invention concerne de nouveaux dérivés de pyrazol de la formule générale (I) dans laquelle R1 à R6 ont la notation mentionnée dans la description. L'invention concerne en outre un procédé permettant de les préparer et leur utilisation comme agents à effet herbicide.
EP97937465A 1996-07-18 1997-07-07 Derives de pyrazolyle-pyrazol substitues, procede permettant de les preparer et utilisation comme agents a effet herbicide Withdrawn EP0915873A1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE19630555A DE19630555A1 (de) 1996-07-18 1996-07-18 Substituierte Pyrazolyl-pyrazolderivate
DE19630555 1996-07-18
PCT/EP1997/003570 WO1998003506A1 (fr) 1996-07-18 1997-07-07 Derives de pyrazolyle-pyrazol substitues, procede permettant de les preparer et utilisation comme agents a effet herbicide

Publications (1)

Publication Number Publication Date
EP0915873A1 true EP0915873A1 (fr) 1999-05-19

Family

ID=7801171

Family Applications (1)

Application Number Title Priority Date Filing Date
EP97937465A Withdrawn EP0915873A1 (fr) 1996-07-18 1997-07-07 Derives de pyrazolyle-pyrazol substitues, procede permettant de les preparer et utilisation comme agents a effet herbicide

Country Status (14)

Country Link
EP (1) EP0915873A1 (fr)
JP (1) JP2000515142A (fr)
KR (1) KR20000067879A (fr)
CN (1) CN1225635A (fr)
AU (1) AU4009497A (fr)
BR (1) BR9710494A (fr)
CA (1) CA2261125A1 (fr)
DE (1) DE19630555A1 (fr)
ID (1) ID17533A (fr)
PL (1) PL331287A1 (fr)
TR (1) TR199900065T2 (fr)
TW (1) TW355124B (fr)
WO (1) WO1998003506A1 (fr)
ZA (1) ZA976329B (fr)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
RU2692792C2 (ru) * 2015-01-23 2019-06-27 Киою Агри Ко., Лтд. Производное замещенного пиразолилпиразола и его применение в качестве гербицида
RU2692793C2 (ru) * 2015-01-23 2019-06-27 Киою Агри Ко., Лтд. Производное замещенного пиразолилпиразола и его применение в качестве гербицида
RU2692790C2 (ru) * 2015-01-23 2019-06-27 Киою Агри Ко., Лтд. Производное замещенного пиразолилпиразола и его применение в качестве гербицида
RU2693461C2 (ru) * 2015-01-23 2019-07-03 Киою Агри Ко., Лтд. Производное замещенного пиразолилпиразола и его применение в качестве гербицида
RU2693467C2 (ru) * 2015-01-23 2019-07-03 Киою Агри Ко., Лтд. Производное замещенного пиразолилпиразола и его применение в качестве гербицида

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR100613212B1 (ko) * 2001-12-20 2006-08-21 가부시키가이샤 에스디에스 바이오테크 신규의 치환된 피라졸 유도체, 그의 제조 방법 및 그것을함유하는 제초제 조성물
AR097245A1 (es) * 2013-08-09 2016-03-02 Kyoyu Agri Co Ltd Derivado de pirazolilpirazol sustituido y su empleo como herbicida
JP6128556B2 (ja) * 2013-08-13 2017-05-17 協友アグリ株式会社 置換ピラゾリルピラゾール誘導体とその除草剤としての使用
JP6097655B2 (ja) * 2013-08-13 2017-03-15 協友アグリ株式会社 置換ピラゾリルピラゾール誘導体とその除草剤としての使用
JP6128555B2 (ja) * 2013-08-13 2017-05-17 協友アグリ株式会社 置換ピラゾリルピラゾール誘導体とその除草剤としての使用
AR103469A1 (es) 2015-01-23 2017-05-10 Kyoyu Agri Co Ltd Derivado de pirazolilpirazol sustituido y su empleo como herbicida
CN107540670B (zh) * 2016-06-23 2021-08-13 湖北相和精密化学有限公司 一种1-(3-氯吡唑并[1，5a]-4，5，6，7-四氢吡啶-2-基)-5-甲胺吡唑-4-甲腈的制备方法

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
IL116507A (en) * 1991-11-13 1997-08-14 Schering Ag Pyrazole derivatives
JP3770403B2 (ja) * 1992-10-12 2006-04-26 協友アグリ株式会社 新規の置換ピラゾール誘導体、その製造法および該化合物の除草剤としての使用
DE4435373A1 (de) * 1994-09-22 1996-03-28 Hoechst Schering Agrevo Gmbh Substituierte Pyrazolyl-pyrazolderivate, Verfahren zu ihrer Herstellung und ihre Verwendung als Mittel mit herbizider Wirkung
DE19532347A1 (de) * 1995-09-04 1997-03-06 Bayer Ag 4-Thiocarbamoyl-1-(3-pyrazolyl)-pyrazole

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO9803506A1 *

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
RU2692792C2 (ru) * 2015-01-23 2019-06-27 Киою Агри Ко., Лтд. Производное замещенного пиразолилпиразола и его применение в качестве гербицида
RU2692793C2 (ru) * 2015-01-23 2019-06-27 Киою Агри Ко., Лтд. Производное замещенного пиразолилпиразола и его применение в качестве гербицида
RU2692790C2 (ru) * 2015-01-23 2019-06-27 Киою Агри Ко., Лтд. Производное замещенного пиразолилпиразола и его применение в качестве гербицида
RU2693461C2 (ru) * 2015-01-23 2019-07-03 Киою Агри Ко., Лтд. Производное замещенного пиразолилпиразола и его применение в качестве гербицида
RU2693467C2 (ru) * 2015-01-23 2019-07-03 Киою Агри Ко., Лтд. Производное замещенного пиразолилпиразола и его применение в качестве гербицида

Also Published As

Publication number Publication date
AU4009497A (en) 1998-02-10
CA2261125A1 (fr) 1998-01-29
ID17533A (id) 1998-01-08
JP2000515142A (ja) 2000-11-14
TR199900065T2 (xx) 1999-04-21
KR20000067879A (ko) 2000-11-25
DE19630555A1 (de) 1998-01-22
PL331287A1 (en) 1999-07-05
ZA976329B (en) 1998-01-19
BR9710494A (pt) 1999-08-17
TW355124B (en) 1999-04-01
CN1225635A (zh) 1999-08-11
WO1998003506A1 (fr) 1998-01-29

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