EP1025078A1 - Carbamates n-aryle-o-aryloxyalkyle substitues et leur utilisation comme herbicides - Google Patents

Carbamates n-aryle-o-aryloxyalkyle substitues et leur utilisation comme herbicides

Info

Publication number
EP1025078A1
EP1025078A1 EP98954368A EP98954368A EP1025078A1 EP 1025078 A1 EP1025078 A1 EP 1025078A1 EP 98954368 A EP98954368 A EP 98954368A EP 98954368 A EP98954368 A EP 98954368A EP 1025078 A1 EP1025078 A1 EP 1025078A1
Authority
EP
European Patent Office
Prior art keywords
cyano
fluorine
methoxy
chlorine
substituted
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Withdrawn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
EP98954368A
Other languages
German (de)
English (en)
Inventor
Hans-Jochem Riebel
Johannes Rudolf Jansen
Peter Heitkämper
Markus Dollinger
Mark-Wilhelm Drewes
Ingo Wetcholowsky
Ernst Rudolf Gesing
Joachim Kluth
Stefan Lehr
Randy Allen Myers
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 AG
Original Assignee
Bayer 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 Bayer AG filed Critical Bayer AG
Publication of EP1025078A1 publication Critical patent/EP1025078A1/fr
Withdrawn legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
    • C07C271/06—Esters of carbamic acids
    • C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
    • C07C271/26—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atom of at least one of the carbamate groups bound to a carbon atom of a six-membered aromatic ring
    • C07C271/28—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atom of at least one of the carbamate groups bound to a carbon atom of a six-membered aromatic ring to a carbon atom of a non-condensed six-membered aromatic ring
    • 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
    • A01N47/20—N-Aryl derivatives thereof

Definitions

  • the invention relates to new substituted N-.
  • Aryl-O-aryloxyalkyl carbamates processes for their preparation and their use as herbicides.
  • N-ryl-O-aryloxyallcyl carbamates such as e.g. the compounds N- (2-chlorophenyl) -O- [l- (3-trifluoromethylphenoxymethyl) propyl] carbamate, N- (2-trifluoromethylphenyl) -O- [1 - (3-trifluoromethyl- phenoxy-methyl) -propyl] -carbamate and N- (3-trifluoromethyl-phenyl) -O- [l- (3-trifluoromethyl-phen-oxymethyl) -propyl] -carbamate, have herbicidal properties (cf. US-A-
  • n 0, 1 or 2
  • n stands for the numbers 0, 1, 2, 3 or 4, with the proviso that the sum of m and n is at least 1 in each individual case,
  • R 1 represents cyano, halogen or, in each case, alkyl or alkoxy, each of which is substituted by cyano, halogen or C1-C4-alkoxy, each having 1 to 4 carbon atoms
  • R 2 represents alkyl which has 1 to 4 carbon atoms and is optionally substituted by cyano, halogen or C 1 -C 4 -alkoxy
  • R 3 represents cyano, fluorine, bromine, iodine or alkyl, alkoxy or alkoxycarbonyl, each optionally substituted by cyano, halogen or C 1 -C 4 -alkoxy, each having up to 4 carbon atoms, and - in the event that m represents 1 or 2 stands - also stands for chlorine, as well
  • R 4 represents cyano, bromine, iodine or in each case optionally substituted by cyano, halogen or C1-C4-alkoxy .Allcyl, alkoxy or alkoxycarbonyl each having up to 4 carbon atoms, and - in the event that m represents 1 or 2 - also stands for fluorine or chlorine,
  • the compounds of the general formula (I) according to the invention contain an asymmetrically substituted carbon atom and can therefore exist in different enantiomeric (R- and S-configured forms) or diasteromeric forms.
  • the invention relates to both the various possible individual enantiomeric or stereoisomeric forms of the compounds of the general formula (I) as well as the mixtures of these stereoisomeric compounds
  • hydrocarbon chains such as alkyl - also in connection with heteroatoms, such as in alkoxy - are each straight-chain or branched
  • the invention preferably relates to compounds of the formula (I) in which
  • n stands for the numbers 0, 1, 2 or 3, with the proviso that the sum of m and n is at least 1 in each individual case
  • R 1 for cyano, fluorine, chlorine, bromine or in each case methyl, ethyl, n- or l- which is optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy
  • R 2 represents methyl, ethyl, n- or l-propyl, n-, I-, s- or t-butyl, each optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy,
  • R 3 represents cyano, fluorine, bromine, iodine or in each case optionally by cyano, fluorine,
  • Ethoxycarbonyl, n- or l-propoxycarbonyl stands, and - if m stands for 1 or 2 - also stands for chlorine, and
  • R 4 is cyano, bromine, iodine or in each case optionally by cyano, fluorine, chloro,
  • the invention relates in particular to compounds of the formula (I) in which
  • n the numbers 0 or 1
  • n stands for the numbers 0, 1 or 2, with the proviso that in each individual case the
  • R 1 represents cyano, fluorine, chlorine, bromine or in each case methyl, ethyl, methoxy or ethoxy which is optionally substituted by fluorine or chlorine,
  • R 2 represents methyl, ethyl, n- or i-propyl, each optionally substituted by fluorine, chlorine, methoxy or ethoxy,
  • R 3 is cyano, fluorine, bromine or in each case optionally by fluorine, chlorine,
  • R 4 for cyano, bromine. Iodine or in each case optionally by fluorine, chlorine,
  • Methoxy or ethoxv substituted methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- or i-propoxy, methoxycarbonyl, ethoxycarbonyl, n- or i-
  • Residual definitions can be combined with one another, that is, also between the specified preferred ranges
  • the new substituted N-aryl-O-aryloxyalkyl carbamates of the general formula (I) are notable for their strong and selective herbicidal activity
  • the new substituted N-aryl-O-aryloxyall yl-carbamates of the general formula (I) show considerably greater herbicidal activity than that previously known compounds N- (2-chlorophenyl) -O- [1 - (3-trifluoromethylphenoxymethyl) propyl] carbamate, N- (2-trifluoromethylphenyl) -O- [l- (3- trifluoromethyl-phenoxymethyl) propyl] carbamate and N- (3-trifluoromethyl-phenyl) -O- [l- (3-trifluoromethyl-phenoxymethyl) propyl] carbamate
  • the compounds of the formula (I) also show fungicidal and insecticidal activity
  • R 3 and R 4 have, for example, the meanings given in the list below:
  • n, R 3 and R 4 have, for example, the meanings given above in Group 1.
  • n, R 3 and R 4 have, for example, the meanings given above in Group 1.
  • n, R 3 and R 4 have, for example, the meanings given above in Group 1.
  • n, R 3 and R 4 have, for example, the meanings given above in Group 1.
  • n, R 3 and R 4 have, for example, the meanings given above in Group 1.
  • n, R 3 and R 4 have, for example, the meanings given above in Group 1.
  • n, R 3 and R 4 have, for example, the meanings given above in Group 1.
  • n, R 3 and R 4 have, for example, the meanings given above in Group 1.
  • n, R 3 and R 4 have, for example, the meanings given above in Group 1.
  • n, R 3 and R 4 have, for example, the meanings given above in Group 1.
  • n, R 3 and R 4 have, for example, the meanings given above in Group 1.
  • n, R 3 and R 4 have, for example, the meanings given above in Group 1.
  • R 3 and R 4 have, for example, the meanings given above in Group 1
  • n, R 3 and R 4 have, for example, the meanings given above in Group 1.
  • n, R 3 and R 4 have, for example, the meanings given above in Group 1.
  • n, R 3 and R 4 have, for example, the meanings given above in Group 1.
  • n, R 3 and R 4 have, for example, the meanings given above in Group 1.
  • n, R 3 and R 4 have, for example, the meanings given above in Group 1.
  • n, R 3 and R 4 have, for example, the meanings given above in Group 1.
  • n, R 3 and R 4 have, for example, the meanings given above in Group 1.
  • n, R 3 and R 4 have, for example, the meanings given above in Group 1.
  • n, R 3 and R 4 have, for example, the meanings given above in Group 1.
  • n, R 3 and R 4 have, for example, the meanings given above in Group 1.
  • n, R 3 and R 4 have, for example, the meanings given above in Group 1.
  • n, R 3 and R 4 have, for example, the meanings given above in Group 1.
  • n, R 3 and R 4 have, for example, the meanings given above in Group 1.
  • n, R 3 and R 4 have, for example, the meanings given above in Group 1.
  • n, R 3 and R 4 have, for example, the meanings given above in Group 1.
  • aryloxyaryl chloroformate to be used as starting materials in the process (a) according to the invention for the preparation of compounds of the formula (I) are generally defined by the formula (II).
  • m, R 1 and R 2 preferably or in particular those meanings which have already been mentioned above in connection with the description of the compounds of the formula according to the invention (I) preferably or as particularly preferred for m, R 1 and R 2
  • the starting materials of the general formula (II) are known and / or can be prepared by processes known per se (cf. US-A-5099059, US-A-5152827,
  • arylamines to be used further as starting materials in process (a) according to the invention are generally defined by the formula (III).
  • n, R 3 and R 4 preferably or in particular have those meanings which have already been mentioned above in connection with the description of the compounds of the formula (I) according to the invention have been indicated preferably or as particularly preferred for n, R 3 and R 4
  • aryloxyalkanols to be used as starting materials in the process (b) according to the invention for the preparation of compounds of the formula (I) are generally defined by the formula (IV).
  • m, R 1 and R 2 preferably or in particular have those meanings, which have already been mentioned above in connection with the description of the compounds of the formula (I) according to the invention preferably or as particularly preferred for m, R 1 and R 2
  • the starting materials of the general formula (IV) are known and / or can be prepared by processes known per se (cf. US-A-5099059, US-A-5152827,
  • ary socyanates to be used further as starting materials in process (b) according to the invention are generally defined by the formula (V).
  • n, R 3 and R 4 preferably or in particular have those meanings which have already been mentioned above in connection with the Description of the compounds of the formula (I) according to the invention preferably or as particularly preferred for n, R 3 and R 4
  • the starting materials of the general formula (V) are known synthetic chemicals.
  • reaction auxiliaries for processes (a) and (b).
  • These preferably include .alkali metal or alkaline earth metal acetates, amides, carbonates, bicarbonates, hydrides, hydroxides or alkanolates, such as sodium, potassium or calcium acetate, lithium, sodium, potassium or calcium amide, sodium, potassium or calcium carbonate, sodium, potassium or calcium hydrogen carbonate, lithium, sodium, potassium or calcium hydride,
  • DBU 1,8-diazabicyclo [5,4,0] undec-7-ene
  • Inert organic solvents are particularly suitable as diluents for carrying out processes (a) and (b) according to the invention.
  • These include in particular aliphatic, alicyclic or aromatic, optionally halogenated hydrocarbons, such as, for example, gasoline, benzene, toluene, xylene, chlorobenzene,
  • Dichlorobenzene petroleum ether, hexane, cyclohexane, dichloromethane, chloroform, carbon tetrachloride; Ethers, such as diethyl ether, diisopropyl ether, dioxane, tetrahydrofuran or ethylene glycol dimethyl or diethyl ether; Ketones, such as acetone, butanone or methyl isobutyl ketone; Nitriles such as acetonitrile, propionitrile or butyronitrile; Amides, such as N, N-dimethylformamide, N, N-dimethylacetamide, N-methylformanilide, N-
  • Methyl pyrrolidone or hexamethyl phosphoric acid triamide Esters such as methyl acetate or ethyl acetate, sulfoxides such as dimethyl sulfoxide, alcohols such as methanol, ethanol, n- or i-propanol, ethylene glycol monomethyl ether, ethylene glycol colmonoethyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, their mixtures with water or pure water
  • reaction temperatures can be varied within a substantial range when carrying out processes (a) and (b) according to the invention. In general, temperatures between 0 ° C and 150 ° C, preferably between 10 ° C and 120 ° C
  • Processes (a) and (b) according to the invention are generally carried out under normal pressure. However, it is also possible to carry out the processes according to the invention under elevated or reduced pressure - generally between 0J bar and 10 bar
  • the starting materials are generally used in approximately aquimolar amounts. However, it is also possible to use one of the components in a large excess.
  • the reaction is generally carried out in a suitable diluent, if appropriate in the presence of a reaction auxiliary, and the reaction mixture is generally stirred at the required temperature for several hours. Working up is carried out according to customary methods (see the production examples)
  • the active compounds according to the invention can be used as defo ants, desiccants, herbicides and, in particular, as herb weed killers. Weeds in the broadest sense are to be understood as all plants which grow up in places where they are undesirable. Whether the substances according to the invention act as total or selective herbicides depends essentially on the amount used
  • the active compounds according to the invention can be used, for example, in the following plants.
  • the compounds are suitable for total weed control, e.g. on industrial and track systems and on paths and squares with and without tree cover.
  • the connections can also be used for weed control in permanent crops, e.g. Forest, ornamental wood, fruit, wine, citrus, nut, banana, coffee, tea, rubber, oil palm, cocoa, berry fruit and hop plants, on decorative and sports turf and pasture land and for selective purposes Weed control can be used in annual crops
  • the compounds of the formula (I) according to the invention are particularly suitable for the selective control of monocotyledon and dicotyledon weeds in monocotyledon and dicotyledon crops both in the pre-emergence and in the post-emergence process
  • the active ingredients can be converted into the customary formulations, such as solutions, emulsions, wettable powders, suspensions, powders, dusts, pastes, soluble powders, granules, suspension emulsion concentrates, active ingredient-impregnated natural and synthetic substances and very fine encapsulations in polymeric substances.
  • formulations are prepared in a known manner, e.g. B. by mixing the active ingredients with extenders, ie liquid solvents and / or solid carriers, optionally using surface-active agents, ie emulsifiers and / or dispersants and / or foam-generating agents.
  • organic solvents can also be used as auxiliary solvents.
  • auxiliary solvents e.g. organic solvents
  • aromatics such as xylene, toluene, or alkylnaphthalamine
  • chlorinated aromatics and chlorinated aliphatic hydrocarbons such as chlorobenzenes, chlorethylenes or methylene chloride
  • aliphatic hydrocarbons such as cyclohexane or paraffins, e.g.
  • Petroleum fractions mineral and vegetable oils, alcohols, such as butanol or glycol and their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents such as dimethylformamide and dimethyl sulfoxide, and water.
  • alcohols such as butanol or glycol and their ethers and esters
  • ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone
  • strongly polar solvents such as dimethylformamide and dimethyl sulfoxide, and water.
  • ammonium salts and natural rock powders such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and synthetic rock powders, such as highly disperse silica, aluminum oxide and silicates, are suitable as solid carriers for granules
  • eg broken and fractionated natural rocks such as calcite, marble, pumice, sepiolite, dolomite as well as synthetic granules from inorganic and organic flours as well as granules from organic material such as sawdust, coconut shells, corn cobs and tobacco stalks
  • Possible emulsifiers and / or foam-generating agents are: for example nonionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulf
  • Adhesives such as carboxymethyl cellulose, natural and synthetic powdery, granular or latex-shaped polymers, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, and natural phospholipids such as cephalins and lecithins and synthetic phospholipids can be used in the formulations.
  • Other additives can be mineral and vegetable oils.
  • Dyes such as inorganic pigments, e.g. Iron oxide, titanium oxide, ferrocyan blue and organic dyes, such as .alizarin, azo and metal phthalocyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, cobalt,
  • Molybdenum and zinc can be used.
  • the formulations generally contain between 0.1 and 95 percent by weight of active compound, preferably between 0.5 and 90%.
  • the active compounds according to the invention can also be used for combating weeds, in a mixture with known herbicides, finished formulations or tank mixes being possible.
  • Carbetamides Carfentrazone (-ethyl), Chlomethoxyfen, Chloramben, Chloridazon, Chlorimuron (-ethyl), Chlornitrofen, Chlorsul roleson, Chlortoluron, Cinmethylin, Cinosul Resultson, Clethodim, Clodinafop (-propargyl), Clomazone, Clomepyronopyronopyridopyromopyromopyromopyron, Clomepyromopyron, Clomepyromopyromopyron, ), Cloransulam (-methyl), cumyluron, cyanazines, cycloates, cyclosulfamuron, cycloxydim, cyhalofop (-butyl), 2,4-D, 2,4-DB, 2,4-DP, desmedipham, dialates, dicamba, Diclofop (-methyl), diclosulam, diethat
  • a mixture with other known active compounds such as fungicides, insecticides, acacids, nematicides, bird repellants, plant nutrients, and soil structure improvers is also possible
  • the active compounds can be used as such, in the form of their formulations or in the use forms prepared therefrom by further dilution, such as ready-to-use solutions, suspensions, emulsions, powders, pastes and granules. Scatter
  • the active compounds according to the invention can be decorated both before and after the plants emerge. They can also be incorporated into the soil before sowing
  • the amount of active ingredient used can vary over a wide range. It depends essentially on the type of effect desired. In general, the application rates are between 1 g and 10 kg of active ingredient per hectare of soil, preferably between 5 g and 5 kg per ha
  • Emulsifier 1 part by weight of allcylaryl polyglycol ether
  • Seeds of the test plants are sown in normal soil. After about 24 hours, the soil is sprayed with the active ingredient preparation in such a way that the desired amounts of active ingredient are applied per unit area.
  • the concentration of the spray liquor is chosen so that the desired amounts of active compound are applied in 1000 l of water / ha.
  • the degree of damage to the plants is rated in% damage compared to the development of the untreated control.
  • Emulsifier 1 part by weight of alkylaryl polyglycol ether
  • Test plants with a height of 5-15 cm are sprayed with the preparation of active compound in such a way that the desired amounts of active compound are applied per unit area.
  • the concentration of the spray broth is chosen so that in

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  • 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 N-aryle-O-aryloxyalkyle-carbamates substitués de la formule générale (I) dans laquelle m vaut 0, 1 ou 2, n vaut 0, 1, 2, 3 ou 4, R<1> désigne cyano, halogène, ou alkyle ou alcoxy dans chaque cas éventuellement substitué par cyano, halogène ou alcoxy C1-C4 et comportant chacun entre 1 et 4 atomes de carbone, R<2> désigne alkyle éventuellement substitué par cyano, halogène ou alcoxy C1-C4 et comportant entre 1 et 4 atomes de carbone, R<3> désigne cyano, fluor, brome, iode ou alkyle, alcoxy ou alcoxycarbonyle éventuellement substitué dans chaque cas par cyano, halogène ou alcoxy C1-C4 et comportant chacun entre 1 et 4 atomes de carbone, et R<4> désigne cyano, brome, iode ou alkyle, alcoxy ou alcoxycarbonyle alcoxy C1-C4 éventuellement substitué dans chaque cas par cyano, halogène ou alcoxy C1-C4, à l'exception du composé N-(2-méthoxy-5-méthyle-phényle)-O[1-(3-trifluorométhylphénoxyméthyle)-propyl]-carbamate. L'invention concerne également des procédés permettant de les préparer et leur utilisation comme herbicides.
EP98954368A 1997-10-20 1998-10-07 Carbamates n-aryle-o-aryloxyalkyle substitues et leur utilisation comme herbicides Withdrawn EP1025078A1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE19746267 1997-10-20
DE1997146267 DE19746267A1 (de) 1997-10-20 1997-10-20 Substituierte N-Aryl-O-aryloxyalkyl-carbamate
PCT/EP1998/006374 WO1999020600A1 (fr) 1997-10-20 1998-10-07 Carbamates n-aryle-o-aryloxyalkyle substitues et leur utilisation comme herbicides

Publications (1)

Publication Number Publication Date
EP1025078A1 true EP1025078A1 (fr) 2000-08-09

Family

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Family Applications (1)

Application Number Title Priority Date Filing Date
EP98954368A Withdrawn EP1025078A1 (fr) 1997-10-20 1998-10-07 Carbamates n-aryle-o-aryloxyalkyle substitues et leur utilisation comme herbicides

Country Status (8)

Country Link
EP (1) EP1025078A1 (fr)
JP (1) JP2001520216A (fr)
CN (1) CN1276787A (fr)
AU (1) AU1151499A (fr)
BR (1) BR9812956A (fr)
CA (1) CA2307344A1 (fr)
DE (1) DE19746267A1 (fr)
WO (1) WO1999020600A1 (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE19842056A1 (de) * 1998-09-15 2000-03-16 Bayer Ag Substituierte N-Aryl-O-alkyl-carbamate

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5099059A (en) * 1990-08-20 1992-03-24 Baker Don R Substituted phenyl carbamates and their use as herbicides

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO9920600A1 *

Also Published As

Publication number Publication date
CN1276787A (zh) 2000-12-13
DE19746267A1 (de) 1999-04-22
CA2307344A1 (fr) 1999-04-29
BR9812956A (pt) 2000-08-08
JP2001520216A (ja) 2001-10-30
WO1999020600A1 (fr) 1999-04-29
AU1151499A (en) 1999-05-10

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