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WO1996021652A1 - Derives 4-aryl- et 4-heteroaryl-5-oxo-pyrazoline possedant des proprietes pesticides - Google Patents

Derives 4-aryl- et 4-heteroaryl-5-oxo-pyrazoline possedant des proprietes pesticides Download PDF

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Publication number
WO1996021652A1
WO1996021652A1 PCT/EP1995/005152 EP9505152W WO9621652A1 WO 1996021652 A1 WO1996021652 A1 WO 1996021652A1 EP 9505152 W EP9505152 W EP 9505152W WO 9621652 A1 WO9621652 A1 WO 9621652A1
Authority
WO
WIPO (PCT)
Prior art keywords
alkyl
substituted
formula
group
cycloalkyl
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/EP1995/005152
Other languages
English (en)
Inventor
Manfred Böger
Peter Maienfisch
Fredrik Cederbaum
Thomas Pitterna
Pradeep Jeevaji Nadkarni
Vadiraj Subbanna Ekkundi
Surendra Umesh Kulkarni
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.)
Novartis AG
Original Assignee
Ciba Geigy AG
Novartis AG
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 Ciba Geigy AG, Novartis AG filed Critical Ciba Geigy AG
Priority to EP95943223A priority Critical patent/EP0804422A1/fr
Priority to MX9705247A priority patent/MX9705247A/es
Priority to AU44353/96A priority patent/AU4435396A/en
Priority to JP8521407A priority patent/JPH10512248A/ja
Publication of WO1996021652A1 publication Critical patent/WO1996021652A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • 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
    • C07D401/12—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 linked by a chain containing hetero atoms as chain links
    • 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
    • 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
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
    • A01N47/18—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing a —O—CO—N< group, or a thio analogue thereof, directly attached to a heterocyclic or cycloaliphatic ring
    • 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
    • C07D231/28—Two oxygen or sulfur atoms
    • C07D231/30—Two oxygen or sulfur atoms attached in positions 3 and 5
    • C07D231/32—Oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04—Ortho-condensed systems

Definitions

  • Examples of the unsubstituted or mono- to trisubstituted, nonaromatic, mono- or bicyclic heterocyclic rings which the substituents R 21 and R 22 , together with the nitrogen atom to which they are attached, are able to form are, for example, 1-pyrrolidinyl, 1-piperidyl, 2,6-dimeu ⁇ yl-1-piperidyl, 4-morpholinyl, 4-methylpiperazin-1-yl, 4-phenylpiperazin-1-yl, 4-benzylpiperazin- 1 -yl, 4-(3,4-dichlorophenyl)piperazin- 1 -yl, 4-thiomorpholinyl, 2,6-dimed ⁇ yl-4-morpholinyl, 2,6-dimethylthio-4-mo ⁇ pholinyl, 1,2,3,4-tetrahydroquinolin-1-yl orindolin-1-yl.
  • ring systems can be substituted by halogen, C 1 -C 16 alkyl, C 1 -C 16 haloalkyl,
  • heterocyclic amines such as, for example, pyridine, quinoline, isoquinoline, morpholine, N-methylmorpholine, thiomorpholine, piperidine, pyrrolidine, indoline, quinuclidine and azepine; primary arylamines such as, for example, anilines, methoxyanilines, ethoxyanilines, o-, m- and p-toluidines, phenylenediamines, benzidines, naphthylamines and o-, m- and p-chloroanilines; but especially triethylamine, isopropylamine and diisopropylamine.
  • heterocyclic amines such as, for example, pyridine, quinoline, isoquinoline, morpholine, N-methylmorpholine, thiomorpholine, piperidine, pyrrolidine, indoline, quinuclidine and azepine
  • A is C 1 -C 8 alkyl substituted by nitro, cyano, Si(C 1 -C 4 alkyl) 3 , amino, C 1 -C 4 alkylamino, di(C 1 -C 4 alkyl)amino, substituted or unsubstituted benzyloxy or a group -CH-NRr ⁇ Rr ⁇ , or A is C 3 -C 8 cycloalkyl which can if desired contain as heteroatom
  • Salts of compounds of the formula I can be convened into the free compounds of the formula I in a customary manner; acid addition salts, for example, by treatment with a suitable basic agent or a suitable ion exchanger reagent, and salts with bases, for example, by treatment with a suitable acid or a suitable ion exchanger reagent.
  • Salts of compounds of the formula I can be converted into other salts of compounds of the formula I in a manner known per se; acid addition salts, for example, can be converted into other acid addition salts, for example, by treating a salt of an inorganic acid, such as a hydrochloride, with an appropriate metal salt, such as a sodium, barium or silver salt, of an acid, for example with silver acetate, in a suitable solvent in which the inorganic salt which forms, for example silver chloride, is insoluble and therefore separates out of the reaction mixture.
  • an inorganic acid such as a hydrochloride
  • an appropriate metal salt such as a sodium, barium or silver salt
  • R 4 is C 1 - or C 2 alkyl in positions 2, 4 and 6 relative to the phenyl linkage site; and n is 3.
  • Aedes spp. Antherigona soccata, Bibio hortulanus, Calliphora erythrocephala, Ceratitis spp., Chiysomyia spp., Culex spp., Cuterebra spp., Dacus spp., Drosophila melanogaster,

Landscapes

  • Life Sciences & Earth Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Dentistry (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Plant Pathology (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)

Abstract

La présente invention se rapporte à de nouveaux dérivés 4-aryl- et 4-hétéroaryl-5-oxo-pyrazoline de la formule (I), efficaces en tant que pesticide. Dans cette formule, R1, R2, R3 et G sont tels que définis dans la revendication 1. L'invention se rapporte également aux compositions comprenant ces composés, à l'utilisation de celles-ci en tant qu'insecticides, acaricides ou herbicides, notamment dans les cultures de végétaux utiles, ainsi qu'à des compositions herbicides sélectives comprenant des composés de la formule (I) et, en tant que phytoprotecteurs, des doses efficaces à titre d'antagoniste d'herbicide, soit d'un dérivé quinoline de la formule (X), dans laquelle R15 et X2 sont tels que définis dans la description, soit d'un dérivé de l'acide 1-phénylazole-3-carboxylique de la formule (XI) dans laquelle E, R16, R17, R18 et R19 sont tels que définis dans la description.
PCT/EP1995/005152 1995-01-13 1995-12-29 Derives 4-aryl- et 4-heteroaryl-5-oxo-pyrazoline possedant des proprietes pesticides Ceased WO1996021652A1 (fr)

Priority Applications (4)

Application Number Priority Date Filing Date Title
EP95943223A EP0804422A1 (fr) 1995-01-13 1995-12-29 Derives 4-aryl- et 4-heteroaryl-5-oxo-pyrazoline possedant des proprietes pesticides
MX9705247A MX9705247A (es) 1995-01-13 1995-12-29 Derivados de 4-aril- y 4-heteroaril-5-oxo-pirazolina que tienen propiedades plaguicidas.
AU44353/96A AU4435396A (en) 1995-01-13 1995-12-29 4-aryl- and 4-heteroaryl -5-oxopyrazoline derivatives having pesticidal properties
JP8521407A JPH10512248A (ja) 1995-01-13 1995-12-29 農薬特性を有する４−アリール−及び４−ヘテロアリール−５−オキソ−ピラゾリン誘導体

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH00108/95 1995-01-13
CH10895 1995-01-13

Publications (1)

Publication Number Publication Date
WO1996021652A1 true WO1996021652A1 (fr) 1996-07-18

Family

ID=4179456

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP1995/005152 Ceased WO1996021652A1 (fr) 1995-01-13 1995-12-29 Derives 4-aryl- et 4-heteroaryl-5-oxo-pyrazoline possedant des proprietes pesticides

Country Status (12)

Country Link
EP (1) EP0804422A1 (fr)
JP (1) JPH10512248A (fr)
CN (1) CN1175248A (fr)
AR (1) AR002020A1 (fr)
AU (1) AU4435396A (fr)
BR (1) BR9600088A (fr)
CA (1) CA2210286A1 (fr)
IL (1) IL116697A0 (fr)
MX (1) MX9705247A (fr)
TR (1) TR199600024A2 (fr)
WO (1) WO1996021652A1 (fr)
ZA (1) ZA96243B (fr)

Cited By (33)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1999047525A1 (fr) * 1998-03-13 1999-09-23 Novartis Ag Derives de 3-hydroxy-4-aryl-5-oxopyrazoline a activite herbicide
WO2000047585A1 (fr) * 1999-02-11 2000-08-17 Novartis Ag Herbicides nouveaux derives de 3-hydroxy-4-aryle-5-pyrazoline en tant qu'herbicides
WO2001017352A1 (fr) * 1999-09-07 2001-03-15 Syngenta Participations Ag Herbicide
WO2001017351A1 (fr) * 1999-09-07 2001-03-15 Syngenta Participations Ag Composition herbicide
WO2001017353A1 (fr) * 1999-09-07 2001-03-15 Syngenta Participations Ag Composition herbicide
US6417370B1 (en) 1998-02-27 2002-07-09 Bayer Aktiengesellschaft Arylphenyl-substituted cyclic keto-enols
US6451843B1 (en) 1998-04-27 2002-09-17 Bayer Aktiengesellschaft Arylphenyl-substituted cyclic keto enols
US6458965B1 (en) 1998-03-26 2002-10-01 Bayer Aktiengesellschaft Aryl phenyl substituted cyclic ketoenols
WO2003013249A1 (fr) * 2001-08-10 2003-02-20 Bayer Cropscience Ag Herbicide selectif a base de substituants, ceto-enols cycliques et phytoprotecteurs
WO2003067984A1 (fr) * 2002-02-13 2003-08-21 Syngenta Participations Ag Composition herbicide
WO2005005428A1 (fr) * 2003-07-14 2005-01-20 Bayer Cropscience Aktiengesellschaft Derives de pyrazolidine-dione a substitution hetaryl avec les caracteristiques d’herbicides
WO2006084663A1 (fr) 2005-02-09 2006-08-17 Syngenta Participations Ag Procede pour la fabrication d’intermediaires
WO2007096058A1 (fr) 2006-02-21 2007-08-30 Bayer Cropscience Ag Cétoénols cycliques à substitution cycloalkyl-phényle
US7268247B2 (en) 2002-12-05 2007-09-11 Syngenta Crop Protection, Inc. Process for the preparation of phenylmalonic acid dinitriles
US7605111B2 (en) 1999-09-07 2009-10-20 Syngenta Crop Protection, Inc. Herbicides
WO2010102758A2 (fr) 2009-03-11 2010-09-16 Bayer Cropscience Ag Cétoénols à substitution halogénoalkylméthylèneoxy-phényle
US7888285B2 (en) 2003-03-14 2011-02-15 Bayer Cropscience Ag 2,4,6-phenyl substituted cyclic ketoenols
US7947704B2 (en) 2004-03-25 2011-05-24 Bayer Cropscience Ag 2,4,6-phenyl-substituted cyclic ketoenols
WO2011098433A1 (fr) 2010-02-15 2011-08-18 Bayer Schering Pharma Aktiengesellschaft Cétoénols cycliques pour thérapie
US8119566B2 (en) 2003-08-14 2012-02-21 Bayer Cropscience Ag 4-biphenyl-substituted pyrazolidin-3,5-dione derivatives
US8202875B2 (en) 2004-07-20 2012-06-19 Bayer Cropscience Ag Selective insecticides based on substituted cyclic ketoenols and safeners
US8247351B2 (en) 2005-12-13 2012-08-21 Bayer Cropscience Ag Insecticidal compositions having improved effect
WO2013110612A1 (fr) 2012-01-26 2013-08-01 Bayer Intellectual Property Gmbh Cétoénols à substitution phénylique destinés à lutter contre des parasites de poisson
US8629084B2 (en) 2004-09-16 2014-01-14 Bayer Cropscience Ag Iodine-phenyl-substituted cyclic cetoenols
US8680339B2 (en) 2009-02-04 2014-03-25 Syngenta Limited Herbicides
WO2014142308A1 (fr) * 2013-03-15 2014-09-18 公益財団法人相模中央化学研究所 Dérivé de pyrazolinone bicyclique et herbicide le comprenant à titre de principe actif
WO2014142307A1 (fr) * 2013-03-15 2014-09-18 公益財団法人相模中央化学研究所 Dérivé de pyrazolinone polycyclique et herbicide le comprenant à titre de principe actif
US8865623B2 (en) 2009-01-15 2014-10-21 Syngenta Limited Herbicidally active cyclic diones and derivatives thereof, processes for their preparation, compositions, and method of controlling weeds
US8895474B2 (en) 2009-01-22 2014-11-25 Syngenta Limited Herbicidally active cyclopentanediones and derivatives thereof, and their use in controlling weeds
US9102642B2 (en) 2009-02-04 2015-08-11 Syngenta Limited Herbicidally active cyclic diones and derivatives thereof, processes for their preparation, compositions, and methods of controlling weeds
WO2021009716A1 (fr) 2019-07-18 2021-01-21 Adam Agan Ltd. Formulation stable comprenant des herbicides
WO2021205448A1 (fr) 2020-04-06 2021-10-14 Adama Agan Ltd. Co-cristaux d'antioxydants et de principes actifs et utilisation d'antioxydants en tant que stabilisants
WO2022041615A1 (fr) * 2020-08-29 2022-03-03 海利尔药业集团股份有限公司 Dérivé de phénylpyrazoline ou son sel, composition et utilisation associées

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DE10326386A1 (de) 2003-06-12 2004-12-30 Bayer Cropscience Ag N-Heterocyclyl-phenylsubstituierte cyclische Ketoenole
CN101580489B (zh) * 2008-05-14 2011-07-20 中国中化股份有限公司 含氮杂环化合物及其制备与应用
ES2529129T3 (es) * 2010-12-02 2015-02-17 Ono Pharmaceutical Co., Ltd. Nuevo compuesto y uso médico del mismo
JP2017214289A (ja) * 2014-09-12 2017-12-07 公益財団法人相模中央化学研究所 ピラゾリノン誘導体、その製造方法及びそれを有効成分として含有する除草剤

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EP0355599A1 (fr) * 1988-08-20 1990-02-28 Bayer Ag Aryl-3 pyrrolidinediones-2,4
EP0508126A1 (fr) * 1991-03-21 1992-10-14 Bayer Ag Dérivés de hydroxy-3-aryl-4-oxo-5-pyrazoline
DE4413669A1 (de) * 1993-07-05 1995-01-12 Bayer Ag Substituierte Aryl-ketoenolheterocyclen

Patent Citations (3)

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EP0355599A1 (fr) * 1988-08-20 1990-02-28 Bayer Ag Aryl-3 pyrrolidinediones-2,4
EP0508126A1 (fr) * 1991-03-21 1992-10-14 Bayer Ag Dérivés de hydroxy-3-aryl-4-oxo-5-pyrazoline
DE4413669A1 (de) * 1993-07-05 1995-01-12 Bayer Ag Substituierte Aryl-ketoenolheterocyclen

Cited By (66)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7288676B2 (en) 1998-02-27 2007-10-30 Bayer Cropscience Ag Arylphenyl-substituted cyclic ketoenols
US7718706B2 (en) 1998-02-27 2010-05-18 Bayer Aktiengesellschaft Arylphenyl-substituted cyclic keto-enols
US6417370B1 (en) 1998-02-27 2002-07-09 Bayer Aktiengesellschaft Arylphenyl-substituted cyclic keto-enols
US7105471B2 (en) 1998-02-27 2006-09-12 Bayer Aktiengesellschaft Arylphenyl-substituted cyclic ketoenols
US6716832B2 (en) 1998-02-27 2004-04-06 Bayer Aktiengesellschaft Arylphenyl-substituted cyclic ketoenols
CZ301369B6 (cs) * 1998-03-13 2010-02-03 Syngenta Participations Ag Herbicidne aktivní deriváty 3-hydroxy-4-aryl-5-oxopyrazolinu
WO1999047525A1 (fr) * 1998-03-13 1999-09-23 Novartis Ag Derives de 3-hydroxy-4-aryl-5-oxopyrazoline a activite herbicide
US6410480B1 (en) 1998-03-13 2002-06-25 Syngenta Crop Protection, Inc. Herbicidally active 3-hydroxy-4-aryl-5-oxopyrazoline derivatives
US6458965B1 (en) 1998-03-26 2002-10-01 Bayer Aktiengesellschaft Aryl phenyl substituted cyclic ketoenols
US6693092B2 (en) 1998-03-26 2004-02-17 Bayer Aktiengesellschaft Arylphenyl-substituted cyclic ketoenols
US6806264B2 (en) 1998-03-26 2004-10-19 Bayer Aktiengesellschaft Arylphenyl-substituted cyclic ketoenols
US6451843B1 (en) 1998-04-27 2002-09-17 Bayer Aktiengesellschaft Arylphenyl-substituted cyclic keto enols
WO2000047585A1 (fr) * 1999-02-11 2000-08-17 Novartis Ag Herbicides nouveaux derives de 3-hydroxy-4-aryle-5-pyrazoline en tant qu'herbicides
US7605111B2 (en) 1999-09-07 2009-10-20 Syngenta Crop Protection, Inc. Herbicides
WO2001017351A1 (fr) * 1999-09-07 2001-03-15 Syngenta Participations Ag Composition herbicide
AU762436B2 (en) * 1999-09-07 2003-06-26 Syngenta Participations Ag Herbicide agent
US7915199B1 (en) 1999-09-07 2011-03-29 Syngenta Crop Protection, Inc. Herbicidal composition
RU2249352C2 (ru) * 1999-09-07 2005-04-10 Зингента Партисипейшнс Аг Гербицидная композиция избирательного действия, способ избирательной борьбы с сорными и травянистыми растениями
RU2251268C2 (ru) * 1999-09-07 2005-05-10 Зингента Партисипейшнс Аг Гербицидная композиция, способ избирательной борьбы с сорными и травянистыми растениями
RU2262846C2 (ru) * 1999-09-07 2005-10-27 Зингента Партисипейшнс Аг Гербицидная композиция, способ борьбы с сорными и травянистыми растениями
US6962894B1 (en) 1999-09-07 2005-11-08 Syngenta Crop Protection, Inc. Herbicidal composition
WO2001017352A1 (fr) * 1999-09-07 2001-03-15 Syngenta Participations Ag Herbicide
RU2251268C9 (ru) * 1999-09-07 2012-12-20 Зингента Партисипейшнс Аг Гербицидная композиция, способ избирательной борьбы с сорными и травянистыми растениями
WO2001017353A1 (fr) * 1999-09-07 2001-03-15 Syngenta Participations Ag Composition herbicide
CN100428885C (zh) * 2001-08-10 2008-10-29 拜尔农作物科学股份公司 基于被取代的环酮烯醇类化合物和安全剂的选择性除草剂
AU2002333283B8 (en) * 2001-08-10 2003-02-24 Bayer Cropscience Ag Selective herbicides based on substituted cyclic keto-enols and safeners
WO2003013249A1 (fr) * 2001-08-10 2003-02-20 Bayer Cropscience Ag Herbicide selectif a base de substituants, ceto-enols cycliques et phytoprotecteurs
RU2320169C2 (ru) * 2001-08-10 2008-03-27 Байер Кропсайенс Аг Селективно-гербицидное средство
AU2002333283B2 (en) * 2001-08-10 2007-03-22 Bayer Cropscience Ag Selective herbicides based on substituted cyclic keto-enols and safeners
US7432225B2 (en) 2001-08-10 2008-10-07 Bayer Cropscience Ag Selective herbicides based on substituted cyclic keto-enols and safeners
WO2003067984A1 (fr) * 2002-02-13 2003-08-21 Syngenta Participations Ag Composition herbicide
US7268247B2 (en) 2002-12-05 2007-09-11 Syngenta Crop Protection, Inc. Process for the preparation of phenylmalonic acid dinitriles
US7888285B2 (en) 2003-03-14 2011-02-15 Bayer Cropscience Ag 2,4,6-phenyl substituted cyclic ketoenols
US7420062B2 (en) 2003-07-14 2008-09-02 Bayer Cropscience, Ag Hetaryl-substituted pyrazolidindione derivatives with pesticidal characteristics
WO2005005428A1 (fr) * 2003-07-14 2005-01-20 Bayer Cropscience Aktiengesellschaft Derives de pyrazolidine-dione a substitution hetaryl avec les caracteristiques d’herbicides
US8987500B2 (en) 2003-08-14 2015-03-24 Bayer Cropscience Ag 4-biphenyl-substituted pyrazolidin-3,5-dione derivatives
US8119566B2 (en) 2003-08-14 2012-02-21 Bayer Cropscience Ag 4-biphenyl-substituted pyrazolidin-3,5-dione derivatives
US8586783B2 (en) 2003-08-14 2013-11-19 Bayer Cropscience Ag 4-biphenyl-substituted pyrazolidin-3,5-dione derivatives
US7947704B2 (en) 2004-03-25 2011-05-24 Bayer Cropscience Ag 2,4,6-phenyl-substituted cyclic ketoenols
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ZA96243B (en) 1996-08-19
EP0804422A1 (fr) 1997-11-05
CN1175248A (zh) 1998-03-04
MX9705247A (es) 1997-10-31
TR199600024A2 (tr) 1996-08-21
CA2210286A1 (fr) 1996-07-18
BR9600088A (pt) 1998-01-27
AR002020A1 (es) 1998-01-07
JPH10512248A (ja) 1998-11-24
AU4435396A (en) 1996-07-31
IL116697A0 (en) 1996-05-14

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