WO2000010971A1 - N-aryl-o-alkylcarbamates substitues - Google Patents

N-aryl-o-alkylcarbamates substitues Download PDF

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Publication number
WO2000010971A1
WO2000010971A1 PCT/EP1999/005909 EP9905909W WO0010971A1 WO 2000010971 A1 WO2000010971 A1 WO 2000010971A1 EP 9905909 W EP9905909 W EP 9905909W WO 0010971 A1 WO0010971 A1 WO 0010971A1
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WO
WIPO (PCT)
Prior art keywords
alkyl
optionally substituted
substituted
methyl
ethyl
Prior art date
Application number
PCT/EP1999/005909
Other languages
German (de)
English (en)
Inventor
Hans-Jochem Riebel
Johannes Rudolf Jansen
Ernst Rudolf F. Gesing
Joachim Kluth
Mark Wilhelm Drewes
Markus Dollinger
Ingo Wetcholowsky
Original Assignee
Bayer Aktiengesellschaft
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 Aktiengesellschaft filed Critical Bayer Aktiengesellschaft
Priority to AU57336/99A priority Critical patent/AU5733699A/en
Publication of WO2000010971A1 publication Critical patent/WO2000010971A1/fr

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Classifications

    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C317/00—Sulfones; Sulfoxides
    • C07C317/26—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
    • C07C317/32—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton with sulfone or sulfoxide groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
    • C07C317/34—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton with sulfone or sulfoxide groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having sulfone or sulfoxide groups and amino groups bound to carbon atoms of six-membered aromatic rings being part of the same non-condensed ring or of a condensed ring system containing that ring
    • C07C317/38—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton with sulfone or sulfoxide groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having sulfone or sulfoxide groups and amino groups bound to carbon atoms of six-membered aromatic rings being part of the same non-condensed ring or of a condensed ring system containing that ring with the nitrogen atom of at least one amino group being part of any of the groups, X being a hetero atom, Y being any atom, e.g. N-acylaminosulfones
    • C07C317/42—Y being a hetero atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C07C323/23—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
    • C07C323/39—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton at least one of the nitrogen atoms being part of any of the groups, X being a hetero atom, Y being any atom
    • C07C323/43—Y being a hetero atom

Definitions

  • the invention relates to new substituted N-aryl-O-alkyl-carbamates, processes for their preparation and their use as herbicides.
  • n 0, 1 or 2
  • Ar represents an optionally substituted, monocyclic or bicyclic, optionally partially saturated, carbocyclic or heterocyclic grouping,
  • Q represents O (oxygen), S (sulfur), SO, SO 2 or CH 2 (methylene),
  • R 1 represents optionally substituted alkyl
  • R 2 stands for halogen or for optionally substituted alkyl or alkoxy
  • R 3 represents hydrogen or alkyl
  • R 4 represents alkyl or cycloalkyl.
  • the compounds of the general formula (I) according to the invention contain at least one asymmetrically substituted carbon atom and can therefore exist in various enantiomeric (R- and S-configured forms) or diasteromeric forms.
  • the invention relates both to the various possible individual enantiomeric or stereoisomeric forms of the compounds of the general formula (I) and to 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), but rather
  • n stands for the numbers 0, 1 or 2.
  • n the numbers 0 or 1
  • Q represents O (oxygen), S (sulfur), SO, SO 2 or CH 2 (methylene),
  • R ' represents alkyl which has 1 to 4 carbon atoms and is optionally substituted by halogen
  • R 2 for halogen or for each optionally substituted by halogen
  • R 3 represents hydrogen or alkyl having 1 to 4 carbon atoms
  • R 4 represents alkyl having 1 to 6 carbon atoms or cycloalkyl having 3 to 6 carbon atoms.
  • the invention relates in particular to compounds of the formula (I) in which
  • n 0, 1 or 2
  • n represents the numbers 0 or 1
  • A stands for methylene or dimethylene (ethane-1,2-diyl) which is optionally substituted by fluorine and / or chlorine, and the possible substituents are preferably selected from the following list:
  • Q represents O (oxygen), S (sulfur), SO, SO 2 or CH 2 (methylene),
  • R for methyl optionally substituted by fluorine and / or chlorine
  • R 2 represents fluorine, chlorine, bromine or methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- or i-propoxy, each of which is optionally substituted by fluorine and / or chlorine,
  • R 3 represents hydrogen, methyl, ethyl, n- or i-propyl
  • R 4 represents methyl, ethyl, n- or i-propyl, or cyclopropyl.
  • a particularly preferred group are those compounds of the formula (I) in which
  • n 0, 1 or 2
  • n the numbers 0 or 1
  • a 1 represents cyano, nitro, fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, methoxy, difluoromethoxy, trifluoromethoxy, methylthio, methylsulfinyl, methylsulfonyl or acetyl and
  • a 2 represents hydrogen, fluorine, chlorine, methyl or trifluoromethyl
  • R 1 represents methyl, difluoromethyl, ethyl, n- or i-propyl
  • R 2 represents fluorine, chlorine, bromine, methyl, ethyl, methoxy or ethoxy,
  • R 3 represents hydrogen, and R 4 represents methyl, ethyl, n- or i-propyl.
  • n is most preferably 0.
  • Ar most preferably represents the grouping below
  • a 1 has the meaning given above.
  • Q most preferably represents oxygen.
  • radical definitions listed above apply both to the end products of the formula (I) and correspondingly to the starting or intermediate products required in each case for the preparation. These radical definitions can be combined with one another, that is to say also between the specified preferred ranges.
  • the new substituted N-aryl-O-alkyl-carbamates of the general formula (I) are notable for their strong and selective herbicidal activity.
  • the compounds of the general formula (I) also have insecticidal activity.
  • the compounds of the general formula (I) in which m represents the number 0 can be reacted with oxygenating agents, such as hydrogen peroxide (H 2 O 2 ) or m-chloroperbenzoic acid, if appropriate in the presence of a diluent such as chloroform or carbon tetrachloride, at temperatures between 0 ° C. and 100 ° C., are converted into corresponding compounds of the general formula (I), in which m then stands for 1 or 2.
  • oxygenating agents such as hydrogen peroxide (H 2 O 2 ) or m-chloroperbenzoic acid
  • a diluent such as chloroform or carbon tetrachloride
  • Formula (II) provides a general definition of the arylamines to be used as starting materials in process (a) according to the invention for the preparation of compounds of the general formula (I).
  • m, n, R 1 , R 2 and R 3 preferably or in particular have those meanings which are preferred or particularly preferred in connection with the description of the compounds of the general formula (I) according to the invention for m, n, R 1 , R 2 and R 3 have been specified.
  • the starting materials of the general formula (II) are known and / or can be prepared by processes known per se (cf. WO-A-97/46540).
  • Formula (III) provides a general definition of the chloroformate esters to be used further as starting materials in process (a) according to the invention.
  • Ar, Q and R 4 preferably or in particular have the those meanings which have already been given above in connection with the description of the compounds of the general formula (I) according to the invention preferably or as particularly preferred for Ar, Q and R 4 .
  • the starting materials of the general formula (III) are known and / or can be prepared by processes known per se (cf. US-A-5099059, US-A-5152827, US-A-5399545).
  • Formula (IV) provides a general definition of the aryl isocyanates to be used as starting materials in process (b) according to the invention for the preparation of compounds of the general formula (I).
  • m, n, R '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 general formula (I) according to the invention preferably or as particularly preferred for m, n, R 1 and R 2 have been specified.
  • the starting materials of the general formula (IV) are known and / or can be prepared by processes known per se (cf. J. Med. Chem. 33 (1990), 1932-1935).
  • Formula (V) provides a general definition of the substituted alkanols to be used further as starting materials in process (b) according to the invention.
  • Ar, Q and R 4 preferably or in particular have those meanings which are preferred or as particularly preferred for Ar, Q and R already in connection with the description of the compounds of the general formula (I) according to the invention 4 have been specified.
  • the starting materials of the general formula (V) are known organic synthetic chemicals.
  • Suitable reaction auxiliaries for processes (a) and (b) according to the invention are generally the customary inorganic or organic bases or acid acceptors. 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,
  • Phase transfer catalysts are also suitable as further reaction aids for processes (a) and (b) according to the invention. As examples of such
  • Tetrabutylammonium bromide Tetrabutylammonium bromide, tetrabutylammonium chloride, tetraoctylammonium chloride, tetrabutylammonium hydrogen sulfate, methyl trioctylammonium chloride, hexadecyl trimethylammonium chloride, hexadecyl trimethylammonium bromide,
  • Suitable diluents for carrying out processes (a) and (b) according to the invention are, in addition to water, above all inert organic solvents.
  • 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-methyl-formanilide, N-methyl-pyrrolidone or hexamethyl-phosphoric acid triamide;
  • Propanol ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, their mixtures with water or pure water.
  • reaction temperatures can be carried out when carrying out the inventive reaction temperatures.
  • Processes (a) and (b) can be varied over a wide range. In general, temperatures between 0 ° C and 120 ° C, preferably between 10 ° C and 80 ° C.
  • the processes 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 0.1 bar and 10 bar.
  • the starting materials are generally used in approximately equimolar amounts. However, it is also possible Lich to use one of the components in a larger excess.
  • the reaction is generally carried out in a suitable diluent in the presence of a reaction auxiliary and the reaction mixture is generally stirred at the required temperature for several hours.
  • the work-up is carried out using customary methods (cf. the manufacturing examples).
  • the active compounds according to the invention can be used as defoliants, desiccants, haulm killers and in particular as weed killers. Weeds in the broadest sense are all plants that grow 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 e.g. can be used in the following plants:
  • Emex Datura, Viola, Galeopsis, Papaver, Centaurea, Trifolium, Ranunculus, Taraxacum.
  • Brassica, lactuca, cucumis, cucurbita Brassica, lactuca, cucumis, cucurbita.
  • the active compounds according to the invention are suitable for combating total weeds, e.g. on industrial and track systems and on paths and squares with and without tree cover.
  • the active compounds according to the invention for weed control in permanent crops e.g. Forest, ornamental trees, fruit, wine, citrus, nut, banana, coffee, tea, rubber, oil palm, cocoa,
  • Berry fruit and hop plants on ornamental and sports turf and pasture land as well as for selective weed control in annual crops.
  • the compounds of formula (I) according to the invention show strong herbicidal activity and a broad spectrum of activity when used on the soil and on above-ground parts of plants. To a certain extent, they are also 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 usual formulations, such as
  • These formulations are prepared in a known manner, e.g. B. by mixing the active ingredients with extenders, that is liquid solvents and / or solid carriers, if appropriate 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 alkylnaphthalenes
  • 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.
  • 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.
  • 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 sulfates
  • Adhesives such as carboxymethyl cellulose, natural and synthetic polymers in the form of powders, granules or latices, 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.
  • Acetochlor Acifluorfen (-sodium), Aclonifen, Alachlor, Alloxydim (-sodium), Ametryne, Amidochlor, Amidosulfuron, Anilofos, Asulam, Atrazine, Azafenidin, Azimsulfuron, Benazolin (-ethyl), Benfuresate, Bensulfuron (-methyl) Benzofenap, Benzoylprop (-ethyl), Bialaphos, Bifenox, Bispyribac (-sodium), Bromobutide, Bromofenoxim, Bromoxynil, Butachlor, Butroxydim, Butylate,
  • Flurprimidol Flurtamone, Fluthiacet (-methyl), Fluthiamide, Fomesafen, Glufosinate (-ammonium), Glyphosate (-isopropylammonium), Halosafen, Haloxyfop (- ethoxy ethyl), Haloxyfop (-P-methyl), Hexazinone, Imazamethabenz (- methyl), imazamethapyr, imazamox, imazapic, imazapyr, imazaquin, imazethapyr, imazosulfuron, iodosulfuron, ioxynil, isopropalin, isoproturon, isouron, isoxaben,
  • a mixture with other known active compounds such as fungicides, insecticides, acaricides, nematicides, bird repellants, plant nutrients and agents which improve soil structure, 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. They are used in the usual way, e.g. by pouring, spraying, spraying, sprinkling.
  • the active compounds according to the invention can be applied both before and after the plants emerge. They can also be worked into the soil before sowing.
  • the amount of active ingredient used can vary over a wide range. It essentially depends 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.
  • the calibration was carried out using unbranched alkan-2-ones (with 3 to 16 carbon atoms) whose logP values are known (determination of the logP values using the
  • the lambda max values were determined using the UV spectra from 200 nm to 400 nm in the maxima of the chromatographic signals.
  • Emulsifier 1 part by weight of alkylaryl 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 amount of active ingredient is applied per unit area.
  • the concentration of the spray liquor is chosen so that the desired amount of active compound is applied in 1000 liters of water per hectare.
  • the degree of damage to the plants is rated in% damage compared to the development of the untreated control.
  • Example B the compound according to Production Example 3 shows, at an application rate of 1000 g / ha, a considerably stronger action against weeds than the known compound (A).
  • Emulsifier 1 part by weight of alkylaryl polyglycol ether
  • active compound 1 part by weight of active compound is mixed with the stated amount of solvent, the stated amount of emulsifier is added and the concentrate is diluted with water to the desired concentration.
  • Test plants with a height of 5-15 cm are sprayed with the active substance preparation in such a way that the desired amounts of active substance are applied per unit area.
  • the concentration of the spray liquor is chosen so that in
  • the degree of damage to the plants is rated in% damage compared to the development of the untreated control.
  • the compound according to Production Example 3 shows, at an application rate of 1000 g / ha, a considerably stronger action against weeds than the known compound (A).

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

Abstract

L'invention concerne de nouveaux N-aryl-O-alkylcarbamates substitués, correspondant à la formule générale (I), dans laquelle: m représente les nombres 0, 1 ou 2; n représente les nombres 0 ou 1; Ar représente un groupement, éventuellement substitué, monocyclique ou bicyclique, éventuellement partiellement saturé, carbocyclique ou hétérocyclique; Q représente O (oxygène), S (soufre), SO, SO2 ou CH2 (méthylène); R1 représente alkyle éventuellement substitué; R2 représente halogène ou alkyle ou alcoxy éventuellement substitué; R3 représente hydrogène ou alkyle et R4 représente alkyle ou cycloalkyle. L'invention concerne également un procédé permettant de produire ces composés, ainsi que leur utilisation comme herbicides.
PCT/EP1999/005909 1998-08-24 1999-08-11 N-aryl-o-alkylcarbamates substitues WO2000010971A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU57336/99A AU5733699A (en) 1998-08-24 1999-08-11 Substituted n-aryl-o-alkyl-carbamates

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19838297.9 1998-08-24
DE1998138297 DE19838297A1 (de) 1998-08-24 1998-08-24 Substituierte N-Aryl-O-alkyl-carbamate

Publications (1)

Publication Number Publication Date
WO2000010971A1 true WO2000010971A1 (fr) 2000-03-02

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ID=7878463

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP1999/005909 WO2000010971A1 (fr) 1998-08-24 1999-08-11 N-aryl-o-alkylcarbamates substitues

Country Status (3)

Country Link
AU (1) AU5733699A (fr)
DE (1) DE19838297A1 (fr)
WO (1) WO2000010971A1 (fr)

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0169169A2 (fr) * 1984-07-18 1986-01-22 Sandoz Ag Composés aromatiques
US5099059A (en) * 1990-08-20 1992-03-24 Baker Don R Substituted phenyl carbamates and their use as herbicides
US5152827A (en) * 1990-08-20 1992-10-06 Imperial Chemical Industries Plc Substituted phenyl carbamates and their use as herbicides

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0169169A2 (fr) * 1984-07-18 1986-01-22 Sandoz Ag Composés aromatiques
US5099059A (en) * 1990-08-20 1992-03-24 Baker Don R Substituted phenyl carbamates and their use as herbicides
US5152827A (en) * 1990-08-20 1992-10-06 Imperial Chemical Industries Plc Substituted phenyl carbamates and their use as herbicides

Also Published As

Publication number Publication date
DE19838297A1 (de) 2000-03-02
AU5733699A (en) 2000-03-14

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