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WO1996010566A1 - Phenylaminosulfonylurees substituees utilisees comme herbicides - Google Patents

Phenylaminosulfonylurees substituees utilisees comme herbicides Download PDF

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Publication number
WO1996010566A1
WO1996010566A1 PCT/EP1995/003709 EP9503709W WO9610566A1 WO 1996010566 A1 WO1996010566 A1 WO 1996010566A1 EP 9503709 W EP9503709 W EP 9503709W WO 9610566 A1 WO9610566 A1 WO 9610566A1
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WO
WIPO (PCT)
Prior art keywords
methyl
compounds
ethyl
substituted
formula
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.)
Ceased
Application number
PCT/EP1995/003709
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German (de)
English (en)
Inventor
Johannes R. Jansen
Mark Wilhelm Drewes
Ernst R. F. Gesing
Hans-Jochem Riebel
Markus Dollinger
Hans-Joachim Santel
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
Priority to AU36085/95A priority Critical patent/AU3608595A/en
Publication of WO1996010566A1 publication Critical patent/WO1996010566A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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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

Definitions

  • the invention relates to novel substituted phenylaminosulfonylureas, to a process for their preparation and to their use as herbicides.
  • A is nitrogen, CH or C-halogen
  • Q is oxygen, sulfur, SO or SO 2 ,
  • R 1 is hydrogen, halogen or each optionally substituted by halogen or C 1 -C 4 alkoxy-substituted alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylamino or dialkylamino each having 1 to 4 carbon atoms in the individual alkyl groups
  • R 2 is halogen or represents in each case optionally halogen or C 1 -C 4 -alkoxy-substituted alkyl, alkoxy, alkylthio, alkylsulfinyl, alkyl- is sulfonyl, alkylamino or dialkylamino having in each case 1 to 4 carbon atoms in the individual alkyl groups,
  • R 3 represents hydrogen, halogen or represents in each case optionally halogen or C 1 -C 4 -alkoxy-substituted alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl or alkoxycarbonyl having in each case 1 to 4 carbon atoms in the individual alkyl groups,
  • R 4 is individually alkyl which is optionally substituted by halogen or C 1 -C 4 -alkoxy and has 1 to 6 carbon atoms,
  • R 5 is individually alkyl optionally substituted by halogen or C 1 -C 4 alkoxy having 1 to 6 carbon atoms, or together with R 4 is alkanediyl having 2 to 5 carbon atoms, and
  • R 6 is hydrogen or optionally halogen, C, -C 4 alkoxy, C, -
  • R 1 and R 2 have the abovementioned meaning, with chlorosulfonyl isocyanate, if appropriate in the presence of a diluent, and the chlorosulfonylureas of the general formula (III) formed in this reaction are reacted.
  • R 1 and R 2 have the abovementioned meaning, with substituted anilines of the general formula (IV)
  • novel substituted phenylaminosulfonylureas of the general formula (I) are distinguished by strong and selective herbicidal activity.
  • the invention preferably compounds of formula (I), in which
  • A is nitrogen, CH or C-halogen
  • Q is oxygen, sulfur, SO or SO 2
  • R 1 is hydrogen, fluorine, chlorine, bromine or in each case optionally substituted by fluorine, chlorine, methoxy or ethoxy alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylamino or dialkylamino each having 1 to 3 carbon atoms in the individual alkyl groups
  • R 2 for fluorine, chlorine, bromine, or in each case optionally by fluorine, chlorine,
  • Methoxy or ethoxy is substituted alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylamino or dialkylamino having in each case 1 to 3 carbon atoms in the individual alkyl groups,
  • R 3 represents hydrogen, fluorine, chlorine, bromine, or represents in each case optionally fluorine, chlorine, methoxy or ethoxy-substituted alkyl, alkoxy, alkylthio,
  • R 4 is individually alkyl optionally substituted by fluorine, chlorine, methoxy or ethoxy having 1 to 4 carbon atoms
  • R 5 is individually optionally substituted by fluorine, chlorine, methoxy or ethoxy substituted alkyl having 1 to 4 carbon atoms, or together with R 4 is Alkandiyl having 2 to 4 carbon atoms
  • R 6 is hydrogen or optionally fluoro, chloro, C 1 -C 3 alkoxy, C 1 -C 3 alkylthio, C 1 -C 3 alkylsulfinyl or C 1 -C 3 AlkylsulfonyI is substituted alkyl having 1 to 4 carbon atoms, wherein the compounds 1- [2- (1,1-dimethoxy-ethyl) phenylsulfamoyl] -3- (4-methyl-6-methoxy-1,3,5-triazine -2-yl) urea and 1 - [2- (1,3-dioxo
  • A is nitrogen or CH
  • Q is oxygen or sulfur
  • R 1 is hydrogen, chlorine or optionally in each case by fluorine, chlorine,
  • Methoxy or ethoxy is substituted methyl, ethyl, methoxy, ethoxy, methylthio, ethylthio, methylamino, ethylamino or dimethylamino,
  • R represents chlorine or represents in each case optionally fluorine, chlorine, methoxy or ethoxy-substituted methyl, ethyl, methoxy, ethoxy, methylthio, ethylthio, methylamino, ethylamino or dimethylamino,
  • R 3 represents hydrogen, fluorine, chlorine, bromine, or represents in each case optionally fluorine, chlorine, methoxy or ethoxy-substituted methyl, ethyl, methoxy, ethoxy, methoxycarbonyl or ethoxycarbonyl,
  • R 4 is individually methyl or ethyl which is optionally substituted by fluorine, chlorine, methoxy or ethoxy,
  • R individually is each methyl or ethyl which is optionally substituted by fluorine, chlorine, methoxy or ethoxy, or together with R 4 is ethane-1,2-diyl (dimethylene) or propane-1,3-diyl (trimethylene), and R 6 is hydrogen or optionally substituted by fluorine, chlorine, methoxy,
  • aminoazines to be used as starting materials in the process according to the invention for the preparation of the compounds of the general formula (I) are generally defined by the formula (II).
  • A, R 1 and R 2 have or, in particular, those meanings which have already been mentioned above in connection with the description of the compounds of the formula (I) as being preferred or as being particularly preferred for A, R 1 and R 2 .
  • the starting materials of formula (II) are known synthetic chemicals.
  • the substituted anilines to be used further as starting materials in the process according to the invention are generally defined by the formula (IV).
  • Q, R 3 , R 4 , R 5 and R 6 preferably or in particular have those meanings which have already been mentioned above in connection with the description of the compounds of formula (I) as being preferred or particularly preferred for Q, R 3 , R 4 , R 5 and R 6 were given.
  • the starting materials of the formula (IV) are likewise known and / or can be prepared by processes known per se (cf .. EP-A 184122; US-P 4592776; Synthesis 1983, 203-205; Liebigs Ann. Chem. 1979, 1130- 1136; manufacturing examples).
  • Formula (I) is preferably carried out using diluents.
  • Suitable diluents are virtually all inert organic solvents. These include, preferably, aliphatic and aromatic, optionally halogenated hydrocarbons, such as pentane, hexane, heptane, cyclohexane, petroleum ether, gasoline, ligroin, benzene, toluene, xylene, methylene chloride,
  • ethers such as diethyl and dibutyl ether, glycol dimethyl ether and diglycol dimethyl ether, tetrahydr
  • Acid acceptors which can be used in the process according to the invention are all acid binders customarily used for such reactions.
  • alkali metal hydroxides such as e.g. Sodium and
  • Potassium hydroxide alkaline earth metal hydroxides such as calcium hydroxide, alkali metal carbonates and alcoholates such as sodium and potassium carbonate, such as sodium and Potassium tert-butylate, further 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).
  • the reaction temperatures can be varied within a substantial range in the process according to the invention. In general, one works at 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 elevated or reduced pressure.
  • the particular starting materials required 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.
  • the workup is carried out in the inventive method in each case by customary methods (see the preparation examples).
  • Salts may optionally 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 formula (I) in a suitable solvent, e.g. Methylene chloride, acetone, tert-butyl methyl ether or toluene, and addition of a suitable base.
  • the salts can then - be isolated by concentration or suction - optionally after prolonged stirring.
  • the active compounds of the invention may e.g. used in the following plants:
  • Brassica, Lactuca, Cucumis, Cucurbita Brassica, Lactuca, Cucumis, Cucurbita.
  • the compounds are useful depending on the concentration for total weed control e.g. on industrial and railway tracks and on paths and squares with and without tree cover.
  • the compounds for weed control in permanent crops e.g. Forestry, ornamental, fruit, wine,
  • the compounds of the formula (I) according to the invention are particularly suitable for the selective control of dicotyledonous weeds in monocots and dicots
  • 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 ingredient Concerning natural and synthetic substances as well as the finest encapsulation in polymeric substances.
  • formulations are prepared in a known manner, for. B .. by mixing the active compounds with extenders, ie liquid solvents and / or solid carriers, optionally using surface-active
  • Agents ie emulsifiers and / or dispersants and / or foam-forming agents.
  • Suitable liquid solvents are essentially: aromatics, such as xylene, toluene, or alkylnaphthalenes, chlorinated aromatics and chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chloroethylenes 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.
  • Suitable solid carriers are:
  • Ammonium salts and ground natural minerals such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, and ground synthetic minerals, such as fumed silica, alumina and silicates, as solid carriers for granules are suitable: e.g. crushed and fractionated natural rocks such as calcite, marble, pumice, sepiolite, dolomite and synthetic granules of inorganic and organic flours and granules of organic material such as sawdust, coconut shells, corn cobs and tobacco stalks; suitable emulsifiers and / or foam formers are: e.g.
  • nonionic and anionic emulsifiers such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, e.g. Alkylaryl polyglycol ethers, alkylsulfonates, alkyl sulfates, arylsulfonates and protein hydrolysates; suitable dispersants are: e.g. Lignin-sulphite liquors and methylcellulose.
  • adhesives such as carboxymethylcellulose, natural and synthetic powdery, granular or latex-like polymers, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, and natural phospholipids such as cephalins and lecithins and synthetic phospholipids.
  • Other additives may 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 are used.
  • the formulations generally contain between 0 and 95% by weight of active ingredient, preferably between 0.5 and 90%.
  • the active compounds according to the invention can be used as such or in their formulations also in admixture with known herbicides for controlling weeds, ready-to-use formulations or tank mixes being possible.
  • herbicides are suitable, for example anilides, eg e. Diflufeni can and Propani l; Arylcarboxylic acids, such. Dichloro-picolinic acid, dicamba and picloram; Aryloxyalkanoic acids, e.g. 2,4-D,
  • Aryloxyphenoxyalkanoic acid esters e.g. Diclofop-methyl, fenoxaprop-ethyl, fluazifop-butyl, haloxy-pent-methyl and quizalofop-ethyl;
  • Azinones such as Chloridazon and norflurazon;
  • Carbamates such as e.g. Chlorpropham, Desmedipham, Phenmedipham and Propham; Chloroacetanilides, e.g.
  • Imidazolinones such as imazethapyr, imazamethabenz, imazapyr and imazaquin
  • Nitriles such as bromoxynil, dichlobenil and ioxynil
  • Oxyacetamides such as mefenacet
  • Sulfonylureas such as amidosulfuron, bensulfuron-methyl, chlorimuron-ethyl, chlorosulfuron, cinosulfuron, metsulfuron-methyl, nicosulfuron, primisulfuron, pyrazosulfuron-ethyl, thif- forsulfuron-methyl, triasulfuron and tribenuron-methyl
  • Thiolcarbamates such as butylates, cycloates, dialkyls, EPTC, esprocarb, molinates, prosulfocarb, thiobencarb and triallates
  • Triazines such as
  • a mixture with other known active ingredients such as fungicides, insecticides, acaricides, nematicides, bird repellents, plant nutrients and soil conditioners is also possible.
  • the active compounds can be used as such, in the form of their formulations or the use forms prepared therefrom by further dilution, such as ready-to-use solutions, suspensions, emulsions, powders, pastes and granules.
  • the application is done 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 incorporated into the soil before sowing.
  • the amount of active ingredient used can vary within a substantial range. It depends essentially on the type of effect desired. In general, the application rates are between 10 g and 10 kg of active ingredient per hectare of soil surface, preferably between 50 g and 5 kg per ha.
  • Emulsifier 1 part by weight of alkylaryl polyglycol ether
  • a suitable preparation of active compound 1 part by weight of active compound is mixed with the stated amount of solvent, the indicated amount of emulsifier is added and the concentrate is diluted with water to the desired concentration.
  • the preparation of active compound is injected test plants, which have a height of 5 - 15 cm, so that the particular desired amounts of active ingredient per unit area are applied.
  • the concentration of the spray mixture is chosen so that in 2000 1 water / ha, the respective desired amounts of active ingredient are applied.
  • the degree of damage of the plants is rated in% damage in comparison to the development of the untreated control.
  • the compound according to Preparation Example 3 exhibits very good compatibility with crop plants, such as e.g. Wheat, strong
  • Emulsifier 1 part by weight of alkylaryl polyglycol ether To prepare a suitable preparation of active compound, 1
  • Seeds of the test plants are sown in normal soil. After 24 hours, the soil is doused with the preparation of active ingredient. It is advisable to keep the amount of water per unit area expediently constant. The concentration of active ingredient in the preparation does not matter, only the application rate of the active ingredient per unit area is decisive. After three weeks, the degree of damage of the plants is rated in% damage in comparison to the development of the untreated control. It means:
  • the compound according to Preparation Example 3 exhibits very good compatibility with crop plants, such as e.g. Cotton, strong activity against weeds (see Table B-1). Further, e.g. the

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  • Life Sciences & Earth Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Dentistry (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Plant Pathology (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Pest Control & Pesticides (AREA)
  • Agronomy & Crop Science (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

L'invention concerne de nouvelles phénylaminosulfonylurées substituées de formule (I), où A représente par ex. N ou CH; Q représente par ex. O ou S; R<1> et R<2> représentent indépendamment l'un de l'autre alkyle C1-C4 ou alcoxy C1-C4; R<3> représente par ex. H, halogène, alkyle C1-C4 ou alcoxy C1-C4; R<4> et R<5> représentent individuellement par ex. alkyle C1-C6 ou conjointement alcanediyle C2-C5; R<6> représente par ex. alkyle C1-C6. L'invention concerne également des sels de composés de formule (I), un procédé de fabrication de ces nouveaux composés et leur utilisation comme herbicides.
PCT/EP1995/003709 1994-10-04 1995-09-21 Phenylaminosulfonylurees substituees utilisees comme herbicides Ceased WO1996010566A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU36085/95A AU3608595A (en) 1994-10-04 1995-09-21 Substituted phenylaminosulphonyl ureas as herbicides

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DEP4435470.3 1994-10-04
DE19944435470 DE4435470A1 (de) 1994-10-04 1994-10-04 Substituierte Phenylaminosulfonylharnstoffe

Publications (1)

Publication Number Publication Date
WO1996010566A1 true WO1996010566A1 (fr) 1996-04-11

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ID=6529933

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP1995/003709 Ceased WO1996010566A1 (fr) 1994-10-04 1995-09-21 Phenylaminosulfonylurees substituees utilisees comme herbicides

Country Status (3)

Country Link
AU (1) AU3608595A (fr)
DE (1) DE4435470A1 (fr)
WO (1) WO1996010566A1 (fr)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE19615900A1 (de) * 1996-04-22 1997-10-23 Bayer Ag Substituierte Sulfonylamino(thio)carbonyl-triazolin(thi)one
DE19707580A1 (de) * 1997-02-26 1998-08-27 Bayer Ag Phenylaminosulfonylharnstoffderivate

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0184122A2 (fr) * 1984-12-03 1986-06-11 Ppg Industries, Inc. Dérivés sulfamoyl urées

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0184122A2 (fr) * 1984-12-03 1986-06-11 Ppg Industries, Inc. Dérivés sulfamoyl urées

Also Published As

Publication number Publication date
AU3608595A (en) 1996-04-26
DE4435470A1 (de) 1996-04-11

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