+

WO1995029167A1 - Urees cyclopropylcarbonyl-phenylaminosulfonyle substituees utilisees comme herbicides - Google Patents

Urees cyclopropylcarbonyl-phenylaminosulfonyle substituees utilisees comme herbicides Download PDF

Info

Publication number
WO1995029167A1
WO1995029167A1 PCT/EP1995/001394 EP9501394W WO9529167A1 WO 1995029167 A1 WO1995029167 A1 WO 1995029167A1 EP 9501394 W EP9501394 W EP 9501394W WO 9529167 A1 WO9529167 A1 WO 9529167A1
Authority
WO
WIPO (PCT)
Prior art keywords
chlorine
alkoxy
halogen
fluorine
formula
Prior art date
Application number
PCT/EP1995/001394
Other languages
German (de)
English (en)
Inventor
Johannes-R. Jansen
Mark-Wilhelm Drewes
Hans-Jochem Riebel
Markus Dollinger
Hans-Joachim Santel
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 AU24062/95A priority Critical patent/AU2406295A/en
Publication of WO1995029167A1 publication Critical patent/WO1995029167A1/fr

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D521/00—Heterocyclic compounds containing unspecified hetero rings
    • 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
    • A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
    • A01N47/36—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the group >N—CO—N< directly attached to at least one heterocyclic ring; Thio analogues thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C225/00—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones
    • C07C225/22—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/02—Systems containing only non-condensed rings with a three-membered ring

Definitions

  • the invention relates to new substituted cyclopropylcarbonylphenylaminosulfonylureas, processes for their preparation and their use as herbicides.
  • N- (4,6-dimethoxypyrimidin-2-yl) -N , - (2-cyclopropylcarbonylphenylaminosulfonyl) urea can be used as a selective herbicide (cf. EP-A 463287 / US-P 5009699).
  • Some alkylcarbonylphenylaminosulfonylureas are known from older patent applications, but have not gained any importance (cf. EP-A 264467 / US-P 4622065).
  • R 1 represents hydrogen, halogen or alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylamino or dialkylamino each having 1 to 4 carbon atoms in the individual alkyl groups, each substituted by halogen or C 1 -C 3 alkoxy,
  • R 2 represents hydrogen or halogen
  • R 3 represents halogen or alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylamino or dialkylamino, each optionally substituted by halogen or C 1 -C 3 alkoxy, each having 1 to 4 carbon atoms in the individual alkyl groups
  • R 4 represents hydrogen, halogen , Formyl or represents in each case optionally substituted by halogen or C 1 -C 3 alkoxy alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylcarbonyl or alkoxycarbonyl each having 1 to 4 carbon atoms in the individual alkyl groups
  • R 4 represents hydrogen, halogen , Formyl or represents in each case optionally substituted by halogen or C 1 -C 3 alkoxy alkyl, alkoxy, alkylthio, alky
  • R 5 represents cyclopropyl optionally substituted by halogen or C 1 -C 4 alkyl, and salts of the compounds of the formula (I) have been found, the compound being N- (4,6-dimethoxy-pyrimidin-2-yl) -N , - (2-Cyclopropylcarbonyl-phenylaminosulfonyl) urea (known from EP-A 463287 / US-P 5009699) is excluded by disclaimer.
  • the new substituted cyclopropylcarbonylphenylaminosulfonylureas of the general formula (I) or their salts are obtained if aminopyrimidines of the general formula (II)
  • R 1 , R 2 and R 3 have the meaning given above, with anilines of the general formula (IV)
  • R 4 and R 5 have the meaning given above, if appropriate in the presence of an acid acceptor and if appropriate in the presence of a diluent, and if appropriate converting the compounds of the formula (I) thus obtained into salts by customary methods.
  • Another possible production method for the compounds of formula (I) according to the invention is outlined below, where R 1 , R 2 , R 3 , R 4 and R 5 have the meaning given above and R for alkyl (in particular for methyl or ethyl), aralkyl (in particular benzyl) or aryl (in particular phenyl):
  • the new substituted cyclopropylcarbonylphenylaminosulfonylureas of the general formula (I) are notable for their strong and selective herbicidal activity.
  • the new compounds of the formula (I) in some cases better tolerated by crop plants, have a considerably stronger herbicidal action than the structurally similar known compound N- (4,6-dimethoxypyrimidin-2-yl) -N '- (2-cyclopropylcarbonyl-phenylaminosulfonyl) -urea.
  • the invention preferably relates to compounds of the formula (I) in which
  • R 1 represents hydrogen, fluorine, chlorine, bromine or alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylamino or dialkylamino, each optionally substituted by fluorine, chlorine, methoxy or ethoxy, each having 1 to 3 carbon atoms in the individual alkyl groups
  • R 2 represents hydrogen, fluorine, chlorine or bromine
  • R 3 represents fluorine, chlorine, bromine or alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylamino or dialkylamino each having 1 to 3 carbon atoms in the individual alkyl groups, each substituted by fluorine, chlorine, methoxy or ethoxy
  • R 4 represents hydrogen, fluorine, chlorine, bromine, formyl or alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylcarbonyl or alkoxycarbonyl, each optionally substituted by fluorine, chlorine, methoxy or ethoxy, each having 1 to 3 carbon atoms in the individual alkyl groups
  • R 5 represents cyclopropyl which is optionally substituted by fluorine, chlorine, methyl or ethyl, with the exception of the compound N- (4,6-dimethoxypyrimidin-2-yl)
  • the invention further preferably relates to sodium, potassium, magnesium, calcium, ammonium, C 1 -C 4 alkyl ammonium, di (C 1 -C 4 alkyl) ammonium, tri ( C 1 -C 4 alkyl) ammonium, C 5 - or C 6 cycloalkyl ammonium and di (C 1 -C 2 alkyl) benzyl ammonium salts of compounds of the formula (I), in which R 1 , R 2 , R 3 , R 4 and R 5 have the meanings preferably given above.
  • the invention relates in particular to compounds of the formula (I) in which
  • R 1 represents hydrogen, chlorine, methyl, ethyl, trifluoromethyl, methoxy, ethoxy, difluoromethoxy, methylthio, ethylthio, methylamino, ethylamino or dimethylamino,
  • R 2 represents hydrogen
  • R 3 represents chlorine, methyl, ethyl, trifluoromethyl, methoxy, ethoxy, difluoromethoxy, methylthio, ethylthio, methylamino, ethylamino or dimethylamino,
  • R 4 represents hydrogen, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, trifluoromethyl, methoxy, methylthio, methylsulfinyl, methylsulfonyl, acetyl or methoxycarbonyl
  • R 5 represents cyclopropyl, with the exception of the compound N- (4,6-dimethoxy-pyrimidin-2-yl) -N '- (2-cyclopropylcarbonyl-phenylaminosulfonyl) urea, which was excluded by disclaimer above.
  • Very particularly preferred groups of compounds of the formula (I) are the compounds of the formulas (IA) and (IB)
  • R 1 , R 2 and R 3 have the meaning given above as being particularly preferred
  • R 4 represents fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, trifluoromethyl, methoxy, methylthio, methylsulfinyl, methylsulfonyl, acetyl or methoxycarbonyl, and
  • R 5 represents cyclopropyl.
  • the general or preferred radical definitions given above apply both to the end products of the formula (I) and correspondingly to the starting materials or intermediates required in each case for the preparation.
  • radical definitions can be combined with one another as desired, that is to say also between the specified ranges of preferred compounds.
  • the hydrocarbon radicals mentioned in the radical definitions, such as alkyl, also in combinations with heteroatoms, such as in alkoxy, alkylthio or alkylamino, are straight-chain or branched, even if this is not expressly stated.
  • Halogen generally represents fluorine, chlorine, bromine or iodine, preferably fluorine, chlorine or bromine, in particular fluorine or chlorine.
  • aminopyrimidines of the formula (II) to be used as starting materials in the process according to the invention are known synthetic chemicals, some of which are commercially available.
  • A represents halogen, formyl or alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylcarbonyl or alkoxycarbonyl each having 1 to 4 carbon atoms in the individual alkyl groups and optionally substituted by halogen or C 1 -C 3 -alkoxy.
  • A preferably represents fluorine, chlorine, bromine, formyl or alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylcarbonyl or alkoxycarbonyl, each optionally substituted by fluorine, chlorine, methoxy or ethoxy, each having 1 to 3 carbon atoms in the individual alkyl groups; especially for fluorine, chlorine, bromine, methyl, trifluoromethyl, methoxy, methylthio, methylsulfinyl, methylsulfonyl, acetyl or methoxycarbonyl.
  • R 5 has the meaning given above, in the presence of a reaction auxiliary, such as, for example, boron (III) chloride and / or aluminum (III) chloride, and optionally in the presence of a diluent, such as, for example, dichloroethane, at temperatures between -20 ° C. and + 100 ° C (see the manufacturing examples).
  • a reaction auxiliary such as, for example, boron (III) chloride and / or aluminum (III) chloride
  • a diluent such as, for example, dichloroethane
  • diluents Practically all inert organic solvents can be used as diluents. These preferably include aliphatic and aromatic, optionally halogenated hydrocarbons such as pentane, hexane, heptane, cyclohexane, petroleum ether, gasoline, ligroin, benzene, toluene, xylene, methylene chloride, ethylene chloride, chloroform, carbon tetrachloride, chlorobenzene and o-dichlorobenzene, ethers such as diethyl - And dibutyl ether, glycol dimethyl ether and diglycol dimethyl ether, tetrahydrofuran and dioxane, ketones such as acetone, methyl ethyl, methyl isopropyl and methyl iso-butyl ketone, esters
  • Acid acceptors which can be used in the process according to the invention are all acid binders which can customarily be used for such reactions.
  • Alkali metal hydroxides such as, for example, sodium and potassium hydroxide, alkaline earth metal hydroxides such as, for example, calcium hydroxide, alkali metal carbonates and alcoholates such as sodium and potassium carbonate, such as sodium and potassium tert-butoxide, and also aliphatic, aromatic or heterocyclic amines, for example triethylamine, trimethylamine, Dimethylaniline, dimethylbenzylamine, pyridine, 1,5-diazabicyclo [4,3,0] non-5-ene (DBN), 1,8-diazabicyclo [5,4,0] undec-7-ene (DBU) and 1,4-diazabicyclo- [2,2,2] octane (DABCO).
  • DBN 1,5-diazabicyclo [4,3,0] non-5-ene
  • DBU 1,8-diazabic
  • reaction temperatures can be varied within a wide range in the process according to the invention. In general, temperatures between -30 ° C and + 80 ° C, preferably at temperatures between -10 ° C and + 60 ° C.
  • the process according to the invention is generally carried out under normal pressure. However, it is also possible to work under increased or reduced pressure.
  • the starting materials required in each case are generally used in approximately equimolar amounts. However, it is also possible to use one of the two components used in each case in a larger excess.
  • the reactions are generally carried out in a suitable diluent in the presence of an acid acceptor, and the reaction mixture is stirred for several hours at the temperature required in each case.
  • Working up in the process according to the invention is carried out in each case by customary methods (cf. the preparation examples).
  • salts can be prepared from the compounds of the general formula (I) according to the invention.
  • Such salts are obtained in a simple manner by customary salt formation methods, for example by dissolving or dispersing a compound of the formula (I) in a suitable solvent, e.g. Methylene chloride, acetone, tert-butyl methyl ether or toluene, and addition of a suitable base.
  • a suitable solvent e.g. Methylene chloride, acetone, tert-butyl methyl ether or toluene
  • the salts can then be isolated - if appropriate after prolonged stirring - by concentration or suction.
  • the active compounds according to the invention can be used, for example, in the following plants: dicotyledon weeds of the genera: Sinapis, Lepidium, Galium, Stellaria, Matricaria, Anthemis, Galinsoga, Chenopodium, Urtica, Senecio, Amaranthus, Portulaca, Xanthium, Convolvulus, Ipomoea, Polygonum, Sesbania , Ambrosia, Cirsium, Carduus, Sonchus, Solanum, Rorippa, Rotala, Lindernia, Lamium, Veronica, Abutilon, Emex, Datura, Viola, Galeopsis, Papaver, Centaurea, Trifolium, Ranunculus, Taraxacum.
  • 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 purposes Weed control can be used 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 both in the pre-emergence and in the post-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.
  • These 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. If water is used as an extender, organic solvents can, for example, also be used as auxiliary 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, for example 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.
  • 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 silicic acid, 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 and synthetic granules from inorganic and organic flours and granules from organic material such as sawdust, coconut shells, corn cobs and tobacco stems; as emulsifying and / or foaming agents are possible: e.g.
  • nonionic 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 liquor and methyl cellulose.
  • 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 phospholipi, can be used in the formulations de, such as cephalins and lecithins and synthetic phospholipids.
  • 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.
  • herbicides are suitable for the mixtures, for example anilides, such as, for example, diflufenican and propanil; Aryl carboxylic acids such as dichloropicolinic acid, dicamba and picloram; Aryloxyalkanoic acids such as 2,4-D, 2,4-DB, 2,4-DP, fluroxypyr, MCPA, MCPP and triclopyr; Aryloxy-phenoxy-alkanoic acid esters, such as, for example, diclofop-methyl, fenoxaprop-ethyl, fluazifop-butyl, haloxyfop-methyl and quizalofopethyl; Azinones such as chloridazon and norflurazon; Carbamates such as chlorpropham, desmedipham, phenmedipham and propham; Chloroacetanilides such as alachlor, acetochlor, butachlor, metazachlor, metolachlor, pretilachlor and propachlor; Di
  • 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 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 2 kg per ha.
  • Example (IV-1) the compounds of the formula (IV) listed in Table 2 below can also be prepared, for example.
  • Emulsifier 1 part by weight of alkylaryl polyglycol ether To prepare a suitable preparation of active compound, mix 1 part by weight of active compound with the stated amount of solvent, add the stated amount of emulsifier and dilute the concentrate 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 the desired amounts of active compound are applied in 2000 l of water / ha.
  • the degree of damage to the plants is rated in% damage compared to the development of the untreated control. It means:
  • the compound according to Preparation Example 3 shows very good tolerance to crop plants, such as Beets, considerably stronger activity against weeds than the known compound (A) (see Table A-1).
  • Emulsifier 1 part by weight of alkylaryl polyglycol ether To prepare a suitable preparation of active compound, mix 1 part by weight of active compound with the stated amount of solvent, add the stated amount of emulsifier and dilute the concentrate with water to the desired concentration.
  • Seeds of the test plants are sown in normal soil. After 24 hours, the active ingredient preparation is poured onto the floor. The amount of water per unit area is expediently kept constant. The concentration of active substance in the preparation is irrelevant, the only decisive factor is the amount of active substance applied per unit area. After three weeks, the degree of damage to the plants is rated in% damage compared to the development of the untreated control. It means:
  • the compound according to Preparation Example 6 shows very good tolerance to crop plants, such as Cotton, considerably more effective against weeds than the known compound (A) (see Table B-1).

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)

Abstract

L'invention concerne de nouvelles urées cyclopropylcarbonyl-phénylaminosulfonyle substituées de la formule (I) dans laquelle les substituants R?1, R2, R3 et R4¿ ont la notation mentionnée dans la description et R5 désigne éventuellement cyclopropyle substitué par halogène ou alkyle C¿1?-C4, ainsi que les sels des composés de la formule (I), à l'exception du composé urée (N-(4,6-diméthoxy-pyrimidin-2-yl)-N'-(2-cyclopropylcarbonyl-phénylaminosulfonyle). L'invention concerne par ailleurs des procédés de préparation de ces nouveaux composés et leur utilisation comme herbicides.
PCT/EP1995/001394 1994-04-26 1995-04-13 Urees cyclopropylcarbonyl-phenylaminosulfonyle substituees utilisees comme herbicides WO1995029167A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU24062/95A AU2406295A (en) 1994-04-26 1995-04-13 Substituted cyclopropylcarbonyl-phenylaminosulphonyl ureas as herbicides

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE4414476A DE4414476A1 (de) 1994-04-26 1994-04-26 Substituierte Cyclopropylcarbonyl-phenylaminosulfonyl-harnstoffe
DEP4414476.8 1994-04-26

Publications (1)

Publication Number Publication Date
WO1995029167A1 true WO1995029167A1 (fr) 1995-11-02

Family

ID=6516438

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP1995/001394 WO1995029167A1 (fr) 1994-04-26 1995-04-13 Urees cyclopropylcarbonyl-phenylaminosulfonyle substituees utilisees comme herbicides

Country Status (3)

Country Link
AU (1) AU2406295A (fr)
DE (1) DE4414476A1 (fr)
WO (1) WO1995029167A1 (fr)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5856576A (en) * 1997-02-04 1999-01-05 American Cyanamid Company Aryne intermediates and a process for the preparation thereof
US6127576A (en) * 1996-12-20 2000-10-03 American Cyanamid Company Aminophenyl ketone derivatives and a method for the preparation thereof
RU2201418C2 (ru) * 1996-12-20 2003-03-27 Американ Цианамид Компани Производные аминофенилкетона и способ их получения
RU2229487C2 (ru) * 1998-05-18 2004-05-27 Дау Глобал Текнолоджиз Инк. Изделия с повышенной температурной эластичностью, изготовленные из облученных и сшитых этиленовых полимеров
US7968703B2 (en) 2005-03-07 2011-06-28 Shire Canada Inc. Process and methods for the preparation of optically active cis-2-hydroxymethyl-4- (cytosin-1'-yl)-1,3-oxathiolane or pharmaceutically acceptable salts thereof

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CZ287105B6 (en) * 1995-06-06 2000-09-13 American Cyanamid Co Process for preparing l-{[2-(cyclopropylcarbonyl)phenyl]sulfamoyl}-3-(4,6-dialkoxy-2-pyrimidinyl)urea and intermediates for such preparation process
US5847140A (en) * 1995-06-06 1998-12-08 American Cyanamid Company Intermediates for the manufacture of herbicidal 1-{ 2-(cyclopropylcarbonyl) Phenyl! Sulfamoyl}-3-(4,6-dialkoxy-2-pyrimidinyl) urea compounds

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0463287A1 (fr) * 1990-06-22 1992-01-02 American Cyanamid Company 1-((0-Cyclopropylcarbonyl)phényl)sulfamoyl)-3-(4,6-diméthoxy-2-pyrimidyl)urée et procédé pour sa préparation
EP0530994A1 (fr) * 1991-08-16 1993-03-10 Merck & Co. Inc. Dérivés de quinazoline utilisés comme inhibiteurs de transcriptase inverse de HIV
US5280007A (en) * 1991-12-18 1994-01-18 American Cyanamid Company Method for safening rice against the phytotoxic effects of a sulfamoyl urea herbicide

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0463287A1 (fr) * 1990-06-22 1992-01-02 American Cyanamid Company 1-((0-Cyclopropylcarbonyl)phényl)sulfamoyl)-3-(4,6-diméthoxy-2-pyrimidyl)urée et procédé pour sa préparation
EP0530994A1 (fr) * 1991-08-16 1993-03-10 Merck & Co. Inc. Dérivés de quinazoline utilisés comme inhibiteurs de transcriptase inverse de HIV
US5280007A (en) * 1991-12-18 1994-01-18 American Cyanamid Company Method for safening rice against the phytotoxic effects of a sulfamoyl urea herbicide

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6127576A (en) * 1996-12-20 2000-10-03 American Cyanamid Company Aminophenyl ketone derivatives and a method for the preparation thereof
RU2201418C2 (ru) * 1996-12-20 2003-03-27 Американ Цианамид Компани Производные аминофенилкетона и способ их получения
US5856576A (en) * 1997-02-04 1999-01-05 American Cyanamid Company Aryne intermediates and a process for the preparation thereof
RU2229487C2 (ru) * 1998-05-18 2004-05-27 Дау Глобал Текнолоджиз Инк. Изделия с повышенной температурной эластичностью, изготовленные из облученных и сшитых этиленовых полимеров
US7968703B2 (en) 2005-03-07 2011-06-28 Shire Canada Inc. Process and methods for the preparation of optically active cis-2-hydroxymethyl-4- (cytosin-1'-yl)-1,3-oxathiolane or pharmaceutically acceptable salts thereof
US8399655B2 (en) 2005-03-07 2013-03-19 Shire Canada Inc. Process and methods for the preparation of optically active cis-2-hydroxymethyl-4-(cytosin-1′-yl)-1,3-oxathiolane or pharmaceutically acceptable salts thereof

Also Published As

Publication number Publication date
DE4414476A1 (de) 1995-11-02
AU2406295A (en) 1995-11-16

Similar Documents

Publication Publication Date Title
DE4327027A1 (de) Imidazoazine
EP0648749A2 (fr) N-cyanoaryle hétérocycles azotés
EP0661276A1 (fr) Dérivés de phénylsulfamoyl-pyrimidyl-urée à activité herbicidiques
WO1995029902A1 (fr) Phenylaminosulfonylurees substituees utilisees comme herbicides
DE4302702A1 (de) Arylaminosulfonylharnstoffe
DE4343831A1 (de) Substituierte Sulfonylharnstoffe
EP0551821A1 (fr) Dérivés d&#39;acides isoxazolecarboxyliques et leur utilisation comme herbicides
EP0642506B1 (fr) Composes sulfonylamino(thio)carbonyles bisubstitues en heterocycle
EP0558999A2 (fr) Dérivés de pyrazole N-arylé comme herbicides
EP0754179A1 (fr) Sulfonylaminocarbonyltriazolinones substituees et leur utilisation comme herbicides
WO1996011188A1 (fr) Sulfonylaminocarbonyltriazolinones comprenant des substituants lies par oxygene et soufre
WO1995029167A1 (fr) Urees cyclopropylcarbonyl-phenylaminosulfonyle substituees utilisees comme herbicides
EP0824528A1 (fr) Composes sulfonylamino(thio)carbonyltriazoline(thi)ones a substituants aryloxy ou arylthio utilises comme herbicides
EP0528212A1 (fr) N-azinyl-N&#39;-(2-éthylsulfinyl-phénylsulfonyl)urées comme herbicides
WO1997032875A1 (fr) Thienylsulfonyl(thio)urees substituees utilisees comme herbicides
WO1994018177A1 (fr) Urees arylaminosulfonyliques
DE19616362A1 (de) N-(2-Alkyl-phenylsulfonyl)-N&#39;-(4,6-dimethoxy-2-pyrimidinyl)-(thio)harnstoffe
WO1995032193A1 (fr) Thiadiazolines substituees servant d&#39;herbicides
WO1996010566A1 (fr) Phenylaminosulfonylurees substituees utilisees comme herbicides
EP0528211A1 (fr) N-azinyl-N&#39;-(2-méthylsulfinyl-phénylsulfonyl)urées comme herbicides
EP0602427A1 (fr) Quinolylsulfonylurées substituées
EP0529402A1 (fr) N-(alcoylthio-3-phényl)-oxazindiones, comme herbicides
DE19530768A1 (de) Salze von N-(2-Cyclopropylcarbonyl-phenylaminosulfonyl)-N&#39;-(4,6-dimethoxy-2-pyrimidinyl) -harnstoff
EP0609733A2 (fr) Herbicides selectifs fondé sur N-azinyl-N&#39;(2-éthylthiophénylsulfonyl)-urées
DE19501843A1 (de) Substituierte Sulfonylharnstoffe

Legal Events

Date Code Title Description
AK Designated states

Kind code of ref document: A1

Designated state(s): AU BB BG BR BY CA CN CZ FI HU JP KR KZ LK NO NZ PL RO RU SK UA US

AL Designated countries for regional patents

Kind code of ref document: A1

Designated state(s): AT BE CH DE DK ES FR GB GR IE IT LU MC NL PT SE BF BJ CF CG CI CM GA GN ML MR NE SN TD TG

DFPE Request for preliminary examination filed prior to expiration of 19th month from priority date (pct application filed before 20040101)
121 Ep: the epo has been informed by wipo that ep was designated in this application
122 Ep: pct application non-entry in european phase
NENP Non-entry into the national phase

Ref country code: CA

点击 这是indexloc提供的php浏览器服务，不要输入任何密码和下载