WO1999065869A1 - N-aryl-o-alkyl-carbamates substitues - Google Patents

N-aryl-o-alkyl-carbamates substitues Download PDF

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Publication number
WO1999065869A1
WO1999065869A1 PCT/EP1999/003898 EP9903898W WO9965869A1 WO 1999065869 A1 WO1999065869 A1 WO 1999065869A1 EP 9903898 W EP9903898 W EP 9903898W WO 9965869 A1 WO9965869 A1 WO 9965869A1
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WIPO (PCT)
Prior art keywords
cyano
alkyl
chlorine
fluorine
substituted
Prior art date
Application number
PCT/EP1999/003898
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German (de)
English (en)
Inventor
Hans-Jochem Riebel
Johannes Rudolf Jansen
Joachim Kluth
Stefan Lehr
Mark Wilhelm Drewes
Markus Dollinger
Ingo Wetcholowsky
Original Assignee
Bayer Aktiengesellschaft
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Filing date
Publication date
Application filed by Bayer Aktiengesellschaft filed Critical Bayer Aktiengesellschaft
Priority to AU45078/99A priority Critical patent/AU4507899A/en
Publication of WO1999065869A1 publication Critical patent/WO1999065869A1/fr

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    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/96—Esters of carbonic or haloformic acids

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
  • n stands for the numbers 0, 1, 2, 3 or 4,
  • R 1 for nitro, cyano, halogen, or for each optionally by cyano
  • R 2 represents hydrogen or alkyl having 1 to 6 carbon atoms optionally substituted by cyano, halogen or C1-C4alkoxy,
  • R 3 represents hydrogen or alkyl optionally substituted by cyano, halogen or C1-C4-alkoxy having up to 6 carbon atoms, and
  • R 4 for nitro, cyano, halogen, or for each optionally by cyano,
  • the compounds of the general formula (I) according to the invention optionally contain an asymmetrically substituted carbon atom and can therefore be present 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 combination with heteroatoms, such as in alkoxy - are each straight-chain or branched.
  • m preferably represents the numbers 0 or 1;
  • n preferably represents the numbers 1, 2 or 3;
  • Q preferably represents O (oxygen), S (sulfur), SO, SO 2 , NH, N (CH 3 ) or CH 2 (methylene);
  • R 1 preferably represents nitro, cyano, fluorine, chlorine, bromine, each alkyl optionally substituted by cyano, fluorine, chlorine, C1-C3-alkoxy, C1-C3-alkylthio, C1-C3-alkylsulfinyl or C1-C3-alkylsulfonyl with 1 to 4 carbon atoms, or for alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylcarbonyl or alkoxycarbonyl, each optionally substituted by fluorine and / or chlorine, each having up to 4 carbon atoms;
  • R 2 preferably represents hydrogen or alkyl which has 1 to 4 carbon atoms and is optionally substituted by cyano, fluorine, chlorine or C 3 -C 3 -alkoxy;
  • R 3 preferably represents hydrogen or optionally by cyano, fluorine,
  • R 4 preferably represents nitro, cyano, fluorine, chlorine, bromine, for each optionally by cyano, fluorine, chlorine, C 1 -C 3 -alkoxy, C1-C3 -alkylthio, C1-C3-
  • Q particularly preferably represents oxygen or sulfur
  • R 1 particularly preferably represents nitro, cyano, fluorine, chlorine, bromine, in each case optionally by cyano, fluorine, chlorine, methoxy, ethoxy, methylthio,
  • Ethylthio methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl substituted methyl, ethyl, n- or i-propyl, or for methoxy, ethoxy, methylthio, ethylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl, ethylsulfonyl, acetyl, propionyl, methoxycarbonyl or ethoxy carbonyl, each optionally substituted by fluorine and / or chlorine;
  • R 2 particularly preferably represents methyl, ethyl, n- or i-propyl
  • R 3 particularly preferably represents hydrogen, methyl, ethyl, n- or i-propyl
  • R 4 particularly preferably represents nitro, cyano, fluorine, chlorine, bromine, in each case optionally substituted by cyano, fluorine, chlorine, methoxy, ethoxy, methylthio, ethylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl Propyl, or for methoxy, ethoxy, methylthio, ethylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl, ethylsulfonyl, each optionally substituted by fluorine and / or chlorine,
  • radicals listed above or those specified in preferred ranges 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 compounds of the general formula (I) also show fungicidal and insecticidal activity.
  • n and R 4 have, for example, the meanings given in the list below:
  • n and R 4 have, for example, the meanings given above in Group 1.
  • n and R 4 have, for example, the meanings given above in Group 1.
  • n and R 4 have, for example, the meanings given above in Group 1.
  • n and R 4 have, for example, the meanings given above in Group 1.
  • n and R 4 have, for example, the meanings given above in Group 1.
  • n and R 4 have, for example, the meanings given above in Group 1.
  • n and R 4 have, for example, the meanings given above in Group 1.
  • n and R 4 have, for example, the meanings given above in Group 1.
  • n and R 4 have, for example, the meanings given above in Group 1.
  • n and R 4 have, for example, the meanings given above in Group 1.
  • n and R 4 have, for example, the meanings given above in Group 1.
  • n and R 4 have, for example, the meanings given above in Group 1.
  • n and R 4 have, for example, the meanings given above in Group 1.
  • n and R 4 have, for example, the meanings given above in Group 1.
  • Group 16 n and R 4 have, for example, the meanings given above in Group 1.
  • n and R 4 have, for example, the meanings given above in Group 1.
  • n and R 4 have, for example, the meanings given above in Group 1.
  • n and R 4 have, for example, the meanings given above in Group 1.
  • n and R 4 have, for example, the meanings given above in Group 1.
  • n and R 4 have, for example, the meanings given above in Group 1.
  • n and R 4 have, for example, the meanings given above in Group 1.
  • n and R 4 have, for example, the meanings given above in Group 1.
  • n and R 4 have, for example, the meanings given above in Group 1.
  • n and R 4 have, for example, the meanings given above in Group 1.
  • n and R 4 have, for example, the meanings given above in Group 1.
  • n and R 4 have, for example, the meanings given above in Group 1.
  • n and R 4 have the meaning given above,
  • Formula (I) chloroformic acid esters to be used as starting materials are generally defined by the formula (II).
  • m, Q, R 1 and R 2 preferably have those meanings which have already been mentioned above in connection with the description of the compounds of the formula (I) as preferred or particularly preferred for m, Q, R 1 and R. 2 were specified.
  • reaction auxiliary e.g. N, N-dimethylformamide
  • diluent such as e.g. Toluene
  • Formula (III) provides a general definition of the arylamines to be used further as starting materials in process (a) according to the invention.
  • n, R 3 and R 4 preferably have those meanings which have already been given above in connection with the description of the compounds of the formula (I) according to the invention as preferred or particularly preferred for n, R 3 and R 4 .
  • the starting materials of the general formula (III) are known synthetic chemicals.
  • Formula (IV) provides a general definition of the substituted alkanols to be used as starting materials in process (b) according to the invention for the preparation of compounds of the formula (I).
  • m, Q, R 1 and R 2 preferably have those meanings which have already been mentioned above in connection with the description of the compounds of the formula (I) as preferred or particularly preferred for m, Q, R 1 and R. 2 were specified.
  • the starting materials of the general formula (IV) are known and / or can be prepared by processes known per se (cf. WO-A-96/16941, production examples).
  • Formula (V) provides a general definition of the aryl isocyanates to be used further as starting materials in process (b) according to the invention.
  • n and R 4 preferably have those meanings which have already been given above in connection with the description of the compounds of the formula (I) according to the invention as preferred or particularly preferred for n and R 4 .
  • the starting materials of the general formula (V) are known 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, sodium, potassium or Calcium amide, sodium, potassium or calcium carbonate, sodium, potassium or calcium hydrogen carbonate, lithium, sodium, potassium or calcium hydride, lithium, sodium, potassium or calcium hydroxide, sodium or potassium -methanolate, -ethanolate, -n- or -i-propanolate, -n-, -i-, -s- or -t-butanolate; basic organic nitrogen compounds such as trimethylamine, triethylamine, tripropylamine, tributylamine, ethyl-diisopropylamine, N, N-dimethyl-cyclohexylamine, di
  • DABCO 1,4-diazabicyclo [2,2,2] octane
  • DBU 1,8-diazabicyclo [5,4,0] undec-7-ene
  • Inert organic solvents are particularly suitable as diluents for 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
  • 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 0.1 bar and 10 bar.
  • the starting materials are generally used in approximately equimolar amounts. However, it is also possible to use one of the components in a large excess.
  • the reaction is optionally carried out in a suitable diluent and, if appropriate, in the presence of a reaction auxiliary, and the reaction mixture is generally carried out for several hours in the first required temperature stirred. Working up is carried out according to customary methods (cf. the production examples).
  • the active compounds according to the invention can be used as defoliants, desiccants, haulm killers and in particular as weed killers.
  • the active compounds according to the invention can e.g. can be used in the following plants:
  • Pisum Solanum, Linum, Ipomoea, Vicia, Nicotiana, Lycopersicon, Arachis, Brassica, Lactuca, Cucumis, Cucurbita.
  • Sorghum Agropyron, Cynodon, Monochoria, Fimbristylis, Sagittaria, Eleocharis, Scirpus, Paspalum, Ischaemum, Sphenoclea, Dactyloctenium, Agrostis, Alopecurus, Apera.
  • 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 compounds 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 ornamental and sports turf and pasture land and for selective weed control in annual crops.
  • the compounds of formula (I) according to the invention are particularly suitable for the selective control of monocotyledon and dicotyledon weeds in monocotyledon and dicotyledon crops, especially in the pre-emergence process.
  • the active compounds can be converted into the customary formulations, such as solutions, emulsions, wettable powders, suspensions, powders, dusts, pastes, soluble powders, granules, suspension emulsion concentrates, active substance-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, that is to say liquid solvents and / or solid carriers, optionally using surface-active agents, that is to say emulsifiers and / or dispersants and / or foam-generating agents.
  • extenders that is to say liquid solvents and / or solid carriers
  • surface-active agents that is to say emulsifiers and / or dispersants and / or foam-generating agents.
  • water is used as an extender, e.g. also organic
  • Solvents are used as auxiliary solvents.
  • aromatics such as xylene, toluene, or alkyl naphthalenes
  • chlorinated aromatics and chlorinated aliphatic hydrocarbons such as chlorobenzenes, chlorethylenes or methylene chloride
  • aliphatic hydrocarbons such as cyclohexane or paraffins, for example petroleum fractions, mineral and vegetable oils
  • alcohols such as butanol or glycol and their ethers and esters
  • ketones such as
  • Possible solid carriers are: e.g. 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: e.g. 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,
  • natural rock powders such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth
  • synthetic rock powders such as highly disperse silica, aluminum oxide and silicates are suitable as solid carriers for granules: e.g. broken and fractionated natural rocks such as calcite, marble, pumice, se
  • coconut shells, corn cobs and tobacco stems as emulsifying and / or foaming agents are possible: e.g. non-ionic and anionic emulsifiers such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, e.g. Alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates and protein hydrolyzates; Possible dispersants are: e.g. Lignin sulfite waste liquor and
  • Methyl cellulose Methyl cellulose.
  • 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, for example 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 (-efhyl), Bialaphos, Bifenox, Bispyribac (-sodium), Bromobutide, Bromofenoxim, Bromoxynil, Butachlor, Butroxydim, Butylate, cafenstrole, Caloxydim, Carbetamide, Carfentrazone (-ethyl), Chlomethoxyidon (Chloronbenchuron), Chlorambenbene -ethyl), chloronitrofen, chlorsulfuron, chlortoluron, cinidon (-ethyl), cinmethylin, cinosulfuron, clethodim, clodinafop (-propargyl), clomazone, clomeprop, clopyralid, clopyrasulfuron (-methyl), cloransulyl (-methyl), cumoransulam (-methyl) Cyanazines, cybutryne,
  • Imazamethapyr Imazamox, Imazapic, Imazapyr, Imazaquin, Imazethapyr, Imazosulfuron, Iodosulfuron, Ioxynil, Isopropalin, Isoproturon, Isouron, Isoxaben, Isoxachlortole, Isoxaflutole, Isoxapyrifop, Lactofenon, Mactropon, Metrapione, Lenacil MCP, Lenacil MCP Metazachlor, metazazthiazuron, metobenzuron, metobromuron, (alpha-) metolachlor, metosulam, metoxuron,
  • Metribuzin Metsulfuron (-methyl), Molinate, Monolinuron, Naproanilide, Napropamide, Neburon, Nicosulfuron, Norflurazon, Orbencarb, Oryzalin, Oxadiargyl, Oxadiazon, Oxasulfuron, Oxaziclomefone, Oxyfluorfen, Paraipatoxin, Paraquathamine Pretilachlor, primisulfuron (methyl), prometryn, propachlor, propanil, propaquizafop, propisochlor,
  • 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 customary manner, for example by watering, spraying, spraying or scattering.
  • the active compounds according to the invention can be applied both before and after emergence of the plants. 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.
  • a mixture of 1.5 g (6 mmol) of l- (3-trifluoromethoxyphenoxymethyl) propanol (racemic) and 0.9 g (6 mmol) of 2,3-dimethylphenyl isocyanate is at 50 ° C. for about 60 minutes heated to 60 ° C and then left for 15 hours at room temperature (approx. 20 ° C).
  • the initially waxy mass gradually solidifies into a crystalline product.
  • a mixture of 6.0 g (24 mmol) of 1- (3-trifluoromethoxyphenoxymethyl) propanol, 2.5 g (24 mmol) of trichloromethyl chloroformate, 0.1 g of N, N-dimethylformamide and 80 ml of toluene is first stirred at room temperature (approx. 20 ° C.) for 2 hours, then at 60 ° C. for 2 hours and finally heated to boiling under reflux for 5 hours. Then the volatile components are carefully distilled off in a water jet vacuum.
  • 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.
  • the compounds according to Preparation Examples 1 and 2 show good compatibility with crop plants, such as Barley, wheat, corn and soybeans, considerably more effective 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-alkyl-carbamates substitués correspondant à la formule générale (I), dans laquelle m, n, Q, R?1, R2, R3 et R4¿ correspondent respectivement à la définition donnée dans la description. L'invention concerne également le procédé de production de ces carbamates et leur utilisation comme herbicides.
PCT/EP1999/003898 1998-06-17 1999-06-05 N-aryl-o-alkyl-carbamates substitues WO1999065869A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU45078/99A AU4507899A (en) 1998-06-17 1999-06-05 Substituted n-aryl-o-alkyl-carbamates

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE1998126940 DE19826940A1 (de) 1998-06-17 1998-06-17 Substituierte N-Aryl-O-alkyl-carbamate
DE19826940.4 1998-06-17

Publications (1)

Publication Number Publication Date
WO1999065869A1 true WO1999065869A1 (fr) 1999-12-23

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AU (1) AU4507899A (fr)
DE (1) DE19826940A1 (fr)
WO (1) WO1999065869A1 (fr)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6451838B1 (en) 2000-05-24 2002-09-17 Pharmacia & Upjohn Company 1-(pyrrolidin-1-ylmethyl)-3-(pyrrol-2-ylmethylidene)-2-indolinone derivatives
US6569868B2 (en) 1998-04-16 2003-05-27 Sugen, Inc. 2-indolinone derivatives as modulators of protein kinase activity
US6599902B2 (en) 2001-05-30 2003-07-29 Sugen, Inc. 5-aralkysufonyl-3-(pyrrol-2-ylmethylidene)-2-indolinone derivatives as kinase inhibitors
US6706709B2 (en) 2000-06-02 2004-03-16 Sugen, Inc. Indolinone derivatives as protein kinase/phosphatase inhibitors

Citations (4)

* 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
US5194661A (en) * 1990-08-20 1993-03-16 Ici Americas Inc. Substituted benzyl carbamates and their use as herbicides
US5399545A (en) * 1992-11-05 1995-03-21 Ciba-Geigy Corporation Substituted benzyl carbamates with herbicial properties
WO1996016941A1 (fr) * 1994-12-02 1996-06-06 Novartis Ag Herbicides a base de carbamate

Patent Citations (4)

* 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
US5194661A (en) * 1990-08-20 1993-03-16 Ici Americas Inc. Substituted benzyl carbamates and their use as herbicides
US5399545A (en) * 1992-11-05 1995-03-21 Ciba-Geigy Corporation Substituted benzyl carbamates with herbicial properties
WO1996016941A1 (fr) * 1994-12-02 1996-06-06 Novartis Ag Herbicides a base de carbamate

Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6569868B2 (en) 1998-04-16 2003-05-27 Sugen, Inc. 2-indolinone derivatives as modulators of protein kinase activity
US6451838B1 (en) 2000-05-24 2002-09-17 Pharmacia & Upjohn Company 1-(pyrrolidin-1-ylmethyl)-3-(pyrrol-2-ylmethylidene)-2-indolinone derivatives
US6482848B2 (en) 2000-05-24 2002-11-19 Sugen Incorporated Prodrugs of 3-(pyrrol-2-ylmethylidene)-2-indolinone derivatives
US6710067B2 (en) 2000-05-24 2004-03-23 Sugen Incorporated Mannich base prodrugs of 3-(pyrrol-2-ylmethylidene)-2-indolinone derivatives
US6716870B2 (en) 2000-05-24 2004-04-06 Sugen, Inc. Prodrugs of 3-(pyrrol-2-ylmethylidene)-2-indolinone derivatives
US7008943B2 (en) 2000-05-24 2006-03-07 Pharmacia & Upjohn Company 1-(Pyrrolidin-1-ylmethyl)-3-(pyrrol-2-ylmethylidene)-2-indolinone derivatives
US7053113B2 (en) 2000-05-24 2006-05-30 Sugen, Inc. Mannich base prodrugs of 3-(pyrrol-2-yl-methylidene)-2-indolinone derivatives
US7112603B2 (en) 2000-05-24 2006-09-26 Agouron Pharmaceuticals, Inc. Prodrugs of 3-(pyrrol-2-ylmethylidene)-2-indolinone derivatives
US6706709B2 (en) 2000-06-02 2004-03-16 Sugen, Inc. Indolinone derivatives as protein kinase/phosphatase inhibitors
US7071332B2 (en) 2000-06-02 2006-07-04 Sugen, Inc. Indolinone derivatives as protein kinase/phosphatase inhibitors
US6599902B2 (en) 2001-05-30 2003-07-29 Sugen, Inc. 5-aralkysufonyl-3-(pyrrol-2-ylmethylidene)-2-indolinone derivatives as kinase inhibitors

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AU4507899A (en) 2000-01-05

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