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EP0971903A1 - Nouveaux derives herbicides d'acide hydroximique - Google Patents

Nouveaux derives herbicides d'acide hydroximique

Info

Publication number
EP0971903A1
EP0971903A1 EP98914884A EP98914884A EP0971903A1 EP 0971903 A1 EP0971903 A1 EP 0971903A1 EP 98914884 A EP98914884 A EP 98914884A EP 98914884 A EP98914884 A EP 98914884A EP 0971903 A1 EP0971903 A1 EP 0971903A1
Authority
EP
European Patent Office
Prior art keywords
alkyl
methyl
yloxy
formula
alkoxy
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.)
Pending
Application number
EP98914884A
Other languages
German (de)
English (en)
Inventor
Olaf Menke
Gerhard Hamprecht
Markus Menges
Robert Reinhard
Peter Schäfer
Cyrill Zagar
Karl-Otto Westphalen
Ulf Misslitz
Helmut Walter
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.)
BASF SE
Original Assignee
BASF SE
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 BASF SE filed Critical BASF SE
Publication of EP0971903A1 publication Critical patent/EP0971903A1/fr
Pending legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more 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, directly attached to ring carbon atoms
    • C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
    • C07D239/52—Two oxygen atoms
    • C07D239/54—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals
    • 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
    • A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
    • C07C251/32—Oximes
    • C07C251/34—Oximes with oxygen atoms of oxyimino groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
    • C07C251/48—Oximes with oxygen atoms of oxyimino groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with the carbon atom of at least one of the oxyimino groups bound to a carbon atom of a six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C265/00—Derivatives of isocyanic acid
    • C07C265/12—Derivatives of isocyanic acid having isocyanate groups bound to carbon atoms of six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more 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, directly attached to ring carbon atoms
    • C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
    • C07D239/56—One oxygen atom and one sulfur atom

Definitions

  • the present invention relates to new substituted hydroximic acid derivatives of the formula I.
  • R 3 is hydrogen, halogen or -CC alkyl
  • R 7 is a Cj_-C 6 alkyl, C 2 -C 6 alkenyl, C 3 -C 6 alkynyl or phenyl-C ⁇ -Cg-alkyl group, these 4 groups being unsubstituted or one or two substituents can wear, each selected from the group consisting of halogen, C ⁇ -C alkoxy, C ⁇ -C 3 alkoxyimino, (C ⁇ -C 3 alkoxy) carbonyl, (C 1 -C 4 alkylamino) carbonyl, di (C 1 -C 3 alkyl) aminocarbonyl and CO-N (C 1 -C 3 alkyl) - (C 1 -C 3 alkoxy), the 4 last-mentioned radicals in turn being a (C ⁇ -C 3 alkoxy) carbonyl or C ⁇ -C alkoxy group can carry;
  • the compounds of the formula I can contain one or more centers of chirality and are then present as mixtures of enantiomers or diastereomers.
  • the invention relates both to the pure enantiomers or diastereomers and to their mixtures.
  • Agriculturally useful salts include, in particular, the salts of those cations or the acid addition salts of those acids whose cations or anions do not adversely affect the herbicidal activity of the compounds I. So come as cations in particular the ions of the alkali metals, preferably sodium and potassium, the alkaline earth metals, preferably calcium, magnesium and barium, and the transition metals, preferably manganese, copper, zinc and iron, as well as the ammonium ion, if desired one to four C ⁇ -C 4 alkyl substituents and / or can carry a phenyl or benzyl substituent, preferably diisopropylammonium, tetramethylammonium, tetrabutylammonium, trimethylbenzylammonium, furthermore phosphonium ions, sulfonium ions, preferably tri (C 1 -C 4 -alkyl) sulfonium, preferably sulfoxonium Tri (-C
  • Anions of useful acid addition salts are primarily chloride, bromide, fluoride, hydrogen sulfate, sulfate, dihydrogen phosphate, hydrogen phosphate, phosphate, nitrate, hydrogen carbonate, carbonate, hexafluorosilicate, hexafluorophosphate, benzoate, and the anions of C 1 -C 4 -alkanoic acids, preferably Formate, acetate, propionate and butyrate.
  • -C 1 -C 6 haloalkyl for: -C 6 alkyl as mentioned above, which is partially or completely substituted by fluorine, chlorine, bromine and / or iodine, for example CH 2 F, CHF 2 , CF 3 , CH 2 C1, CH (C1), C (C1) 3 , chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1-fluoroethyl, 2-fluoroethyl, 2, 2-difluoroethyl, 2, 2, 2-trifluoroethyl, 2-chloro-2-fluoroethyl ,
  • C 2 -C 6 ⁇ alkenyl for: ethenyl, prop-1-en-l-yl, prop-2-en-l-yl, 1-methylethenyl, n-buten-1-yl, n-buten-2-yl , n-buten-3-yl, 1-methyl-prop-1-en-1-yl, 2-methyl-prop-1-en-1-yl, 1-methyl-prop-2-en-1-yl , 2-methyl-prop-2-en-l-yl, n-penten-1-yl, n-penten-2-yl, n-penten-3-yl, n-penten-4-yl, 1-methyl - but-1-en-l-yl, 2-methyl-but-l-en-l-yl, 3-methyl-but-1-en-l-yl, l-methyl-but-2-en-l -yl, 2-methyl-but-2-en-1-yl, 3-methyl-but-2-en-1-yl, 1-methyl-
  • Suitable solvents or diluents are e.g. aliphatic or cyclic ethers such as diethyl ether and tetrahydrofuran, aliphatic ketones such as acetone, hydrocarbons such as n-pentane, cyclohexane and petroleum ether, aromatic hydrocarbons such as benzene and toluene, halogenated aliphatic or aromatic hydrocarbons such as dichloromethane and chlorobenzene, esters such as ethyl acetate, amides such as dimethyl form - Amide and N-methyl-pyrrolidone, sulfoxides such as dimethyl sulfoxide, and mixtures of these solvents.
  • the alcohols and alcohol derivatives themselves are also suitable as solvents or diluents.
  • the compounds of formula VII are new. For their part, they can be obtained by one of the processes described above for the preparation of compounds I.
  • the reaction temperature is usually 20 to 200 ° C, preferably 40 ° C to the boiling point of the reaction mixture.
  • condensation aids come e.g. Oxalyl chloride, carbonyldiimidazole, carbodiimides such as dicyclohexylcarbodiimide, halogenating agents such as thionyl chloride, phosphorus oxychloride, phosgene, phosphorus trichloride and phosphorus pentachloride, or methyl or ethyl chloroformate into consideration.
  • Hydroxylamines which are available in the form of their salts, in particular as hydrochlorides, hydrobromides or sulfates, or are obtained as salts in the preparation, can, before their reaction with VIII, if desired also in the reaction, mixture with the condensation aid and VIII, by adding a suitable base.
  • the compounds I and their agriculturally useful salts are suitable - both as isomer mixtures and in the form of the pure isomers - as herbicides.
  • the herbicidal compositions containing I control vegetation very well on non-cultivated areas, particularly when high amounts are applied. In crops such as wheat, rice, corn, soybeans and cotton, they act against weeds and grass weeds without significantly damaging the crop plants. This effect occurs especially at low application rates.

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)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

L'invention concerne de nouveaux dérivés d'acide hydroximique de la formule (I), ainsi que leurs sels. Dans cette formule, X = O, S; Y = O, S; R<1> = H, alkyle C1-C4, NH2, alkylamino C1-C4 ou di(alkyle C1-C4)amino; R<2> = halogénure d'alkyle C1-C3; R<3> = H, halogène, alkyle C1-C4; R<4> = H, halogène; R<5> = CN, halogène; R<6> = alkyle C1-C6, alkényle C2-C6, alkinyle C3-C6 ou phényle-alkyle C1-C6, le composé cyclique phényle de ce groupe pouvant être non substitué ou porter entre 1 et 3 substituants; R<7> = un groupe alkyle C1-C6, alkényle C2-C6, alkinyle C3-C6 ou phényle-alkyle C1-C6, ces quatre groupes pouvant être non substitués ou porter 1 ou 2 substituants. Ces nouveaux dérivés et leurs sels s'utilisent comme herbicides; pour la dessiccation/défoliation de plantes.
EP98914884A 1997-03-25 1998-03-12 Nouveaux derives herbicides d'acide hydroximique Pending EP0971903A1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE19712408 1997-03-25
DE19712408 1997-03-25
PCT/EP1998/001440 WO1998042681A1 (fr) 1997-03-25 1998-03-12 Nouveaux derives herbicides d'acide hydroximique

Publications (1)

Publication Number Publication Date
EP0971903A1 true EP0971903A1 (fr) 2000-01-19

Family

ID=7824505

Family Applications (1)

Application Number Title Priority Date Filing Date
EP98914884A Pending EP0971903A1 (fr) 1997-03-25 1998-03-12 Nouveaux derives herbicides d'acide hydroximique

Country Status (8)

Country Link
US (1) US6387849B1 (fr)
EP (1) EP0971903A1 (fr)
JP (1) JP2001517231A (fr)
AR (1) AR012175A1 (fr)
AU (1) AU6921398A (fr)
CA (1) CA2283672A1 (fr)
WO (1) WO1998042681A1 (fr)
ZA (1) ZA982468B (fr)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1127053A1 (fr) * 1998-11-02 2001-08-29 Basf Aktiengesellschaft Nouveaux 1-aryl-4-thiouraciles
EP1125931A1 (fr) * 2000-02-17 2001-08-22 Hunan Research Institute of Chemical Industry (Hétéro)aryl-kétoxime-O-éthers alkyle substitués et méthode pour les fabriquer
KR102871914B1 (ko) * 2020-10-29 2025-10-15 니혼노야쿠가부시키가이샤 옥심기를 갖는 함질소 축합복소환 화합물 및 상기 화합물을 함유하는 농원예용 제초제 및 이들의 사용 방법
CN119775214A (zh) * 2024-12-31 2025-04-08 青岛金尔农化研制开发有限公司 一种取代的肟基芳香类化合物及其制备方法、除草组合物和应用

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
HU219159B (hu) 1989-06-29 2001-02-28 Novartis Ag. 3-Aril-uracil-származékok, ezeket hatóanyagként tartalmazó herbicid készítmény és eljárás a hatóanyag előállítására, valamint gyomnövények irtására
AU627906B2 (en) 1989-07-14 1992-09-03 Nissan Chemical Industries Ltd. Uracil derivatives and herbicides containing the same as active ingredient
EP0473551A1 (fr) 1990-08-31 1992-03-04 Ciba-Geigy Ag Dérivés de 3-arylaracile, procédé pour leur préparation et herbicides les contenant
US5266554A (en) 1990-08-31 1993-11-30 Ciba-Geigy Corporation Heterocyclic compounds
EP0542685A1 (fr) * 1991-11-13 1993-05-19 Ciba-Geigy Ag Dérivés du 3-Aryluracile et leur utilisation dans la lutte contre les mauvaises herbes
DE4424791A1 (de) 1994-07-14 1996-01-18 Basf Ag Substituierte Zimtoxim- und Zimthydroxamid-Derivate

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO9842681A1 *

Also Published As

Publication number Publication date
AU6921398A (en) 1998-10-20
ZA982468B (en) 1998-09-25
WO1998042681A1 (fr) 1998-10-01
CA2283672A1 (fr) 1998-10-01
US6387849B1 (en) 2002-05-14
JP2001517231A (ja) 2001-10-02
AR012175A1 (es) 2000-09-27

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