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WO1994018177A1 - Urees arylaminosulfonyliques - Google Patents

Urees arylaminosulfonyliques

Info

Publication number
WO1994018177A1
WO1994018177A1 PCT/EP1994/000138 EP9400138W WO9418177A1 WO 1994018177 A1 WO1994018177 A1 WO 1994018177A1 EP 9400138 W EP9400138 W EP 9400138W WO 9418177 A1 WO9418177 A1 WO 9418177A1
Authority
WO
WIPO (PCT)
Prior art keywords
alkoxy
halogen
alkyl
optionally substituted
hydrogen
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/EP1994/000138
Other languages
German (de)
English (en)
Inventor
Hans-Jochem Riebel
Hans-Joachim Santel
Markus Dollinger
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 AU59692/94A priority Critical patent/AU5969294A/en
Publication of WO1994018177A1 publication Critical patent/WO1994018177A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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

Definitions

  • the invention relates to new arylaminosulfonylureas, processes for their preparation and their use as herbicides.
  • aminosulfonylureas e.g. N- (4-methoxy-6-methyl-s-triazin-2-yl) -N '- (2-methyltMophenylaminosulfonyl) urea and N- (4,6-dimethyl-pyrimidm-2-yl) -N '- (2-methylthio-phenyl_unmosulfonyl) -ha ⁇ stoflF, have herbicidal properties (see. DE-OS 3243533).
  • R 1 represents in each case optionally substituted alkyl having 2 to 10 carbon atoms, aryl or aralkyl,
  • R2 represents hydrogen, hydroxy, cyano, alkoxycarbonyl or for optionally substituted alkyl, alkenyl, alkynyl, alkoxy, alkenyloxy, aralkyloxy, alkylcarbonyl, cycloalkylcarbonyl, arylcarbonyl, alkylsulfonyl or arylsulfonyl,
  • R * - * stands for hydrogen or for optionally substituted alkyl, alkenyl, alkynyl or aralkyl
  • X represents hydrogen, halogen, cycloalkyl or optionally substituted alkyl, alkoxy, alkylthio, alkylamino or dialkylamino
  • Y represents hydrogen, halogen or optionally substituted alkyl, alkoxy, alkylthio, alkylamino or dialkylamino and
  • Z represents nitrogen or the grouping C-R ⁇ , wherein
  • R4 represents hydrogen, halogen, alkyl or alkoxy
  • R--, R- * R * - * , X, Y and Z have the meaning given above and R ⁇ for alkyl (in particular methyl or ethyl), aralkyl (in particular benzyl) or aryl (in particular phenyl):
  • the new arylaminosulfonylureas of the general formula (I) are notable for strong herbicidal activity. Surprisingly, the new compounds of the formula (I) have a considerably stronger herbicidal action than the structurally similar known compound N- (4-methoxy-6-methyl-s-triazin-2-yl) -N '- (2-methylthio- phenylaminosulfonyl) urea.
  • the invention preferably relates to compounds of the formula (I) in which
  • R2 for hydrogen, hydroxy, cyano, Ci-Cg-alkoxy-carbonyl, for Cj-Cö-alkyl optionally substituted by halogen, cyano, carboxy, C * (-C4-alkylcarbonyl or Cj-C4-alkoxycarbonyl, for each optionally substituted by halogen C3-Cg-alkenyl or C3-C6-alkynyl, for Cj-Cö-alkoxy or C3-Cg-alkenyloxy, for optionally by halogen, C1-C4-alkyl, Cj-C4-haloalkyl, C ⁇ -C4 ⁇ alkoxy, Cj-C4-haloalkoxy, C * --C4-alkoxy-carbonyl, cyano or nitro substituted benzyloxy, for each Ci-Cg-alkylcarbonyl, C3-C6-cycloalkyl optionally substituted by halogen -carbonyl
  • X for hydrogen, halogen, cyclopropyl, for C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -alkylthio, C] -C 4 -alkylamino, each optionally substituted by halo or C 1 -C 4 -alkoxy, or represents di (C 3 -C 3 -alkyl) amino
  • Y for hydrogen, halogen, for C-1-C4-alkyl optionally substituted by halogen or C ] - C4-alkoxy, C * ! -C4-alkoxy, C ⁇ -C4- alkylthio, C ] - C4- alkylamino, or for di- (C * ⁇ -C3-alkyl) -amino
  • Y for hydrogen, halogen, for C-1-C4-alkyl optionally substituted by halogen or C ] - C4-alkoxy
  • Z represents nitrogen or the grouping CR 4 , wherein
  • R 4 represents hydrogen, halogen, C 1 -C 4 alkyl or C -C 4 alkoxy.
  • the invention further preferably sodium, potassium, magnesium, calcium, ammonium, -C-C4-alkyl-ammonium, di- (C] -C4-all_yl) -ammonium-, tri- (C ⁇ -C4 -alkyl) -ammonium, C5- or Cö-cycloalkyl-ammonium and di- (C * --C2-alkyl) -benzyl-ammonium salts of compounds of formula (I), in which n, R--, R2_R * - * , X, Y and Z have the meanings preferably given above.
  • the invention relates in particular to compounds of the formula (I) in which
  • Rl represents ethyl, n- or i-propyl, n-, i- or s-butyl or phenyl
  • R2 represents hydrogen, methyl, ethyl, n- or i-propyl, n-, i- or s-butyl,
  • R ⁇ represents hydrogen, methyl or ethyl
  • X represents hydrogen, fluorine, chlorine, bromine, cyclopropyl, methyl, ethyl, trifluoromethyl, methoxy, ethoxy, difluoromethoxy, methylthio, ethylthio, methylamino, ethylamino or dimethylamino,
  • Y represents hydrogen, fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, methoxy, ethoxy, difluoromethoxy, methylthio, ethylthio, methylamino, ethylamino or dimethylamino, and
  • Z represents nitrogen or the grouping CR 4 , wherein
  • R 4 represents hydrogen, fluorine, chlorine, bromine, methyl or methoxy.
  • hydrocarbon radicals mentioned in the radical definitions such as alkyl, alkenyl or alkynyl, 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.
  • aminoazines 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.
  • arylamines of the formula (IV) which are also required as starting materials are also known and / or can be prepared by processes known per se (cf. DE-OS 3528033).
  • the process according to the invention for the preparation of the new arylaminosulfonylureas of the formula (I) is preferably carried out using 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 isobutyl ketone, esters such as methyl acetate and ethyl acetate, and nitriles such as, for example Acetonitrile and propionitrile, amides such as e.g. Dimethylform
  • 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 e.g. Sodium and potassium hydroxide, alkaline earth metal hydroxides such as e.g.
  • DBN 1,5-diazabicyclo [4,3,0] - non-5-ene
  • DBU 1,8-diazabicyclo- [5,4,0] -undec-7-ene
  • DBUCO 1,4-diazabicyclo- [2,2 , 2] octane
  • reaction temperatures can be varied within a wide range in the process according to the invention. Generally 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 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 by evaporation or suction, if appropriate after prolonged stirring.
  • 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:
  • 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 can be used for selective weed control in annual crops.
  • the compounds of formula (I) according to the invention are particularly suitable for the selective control of dicotyledon weeds in monocotyledon crops, especially 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, and soluble Before powders, granules, suspension emulsion concentrates, active ingredient-impregnated natural and synthetic substances as well as fine encapsulation in polymeric substances.
  • formulations are prepared in a known manner, e.g. B. by mixing the active ingredients with extenders, ie liquid solvents and / or solid carriers, optionally using surface-active agents, ie emulsifiers and / or dispersants and / or foam-generating agents.
  • organic solvents can also be used as auxiliary solvents.
  • auxiliary solvents e.g. organic solvents
  • aromatics such as xylene, toluene, or 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.
  • 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: 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 sulfate leaching and methyl cellulose.
  • Adhesives such as carboxymethylcellulose, natural and synthetic powdery, granular or latex-shaped polymers can be used in the formulations, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, and natural phospholipids, 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, for example, 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 quizalofop-ethyl; Azinones such as chloridazon and norflurazon; Carbamates such as chloropropham, desmedipham, phenmedipham and propham; Chloroacetanilides, such as, for example, alachlor, acetochlor, butachlor, metazachlor, metolachlor
  • 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 applied can vary over a wide range. It essentially depends 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, preferably between 50 g and 5 kg per ha.
  • 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 which have 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 particular amounts of active compound desired are applied in 2000 l of water / ha. After three weeks, the degree of damage to the plants is rated in% damage in comparison to the development of the untreated control.

Landscapes

  • 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 urées arylaminosulfonyliques de la formule générale (I) dans laquelle R1 désigne alkyle éventuellement substitué ayant entre 2 et 10 atomes de carbone, aryle ou aralkyle, R2 désigne hydrogène, hydroxy, cyano, alcoxycarbonyle ou alkyle éventuellement substitué, alcényle, alcinyle, alcoxy, alcényloxy, aralkyloxy, alkylcarbonyle, cycloalkylcarbonyle, arylcarbonyle, alkylsulfonyle ou arylsulfonyle, R3 désigne hydrogène ou alkyle éventuellement substitué, alcényle, alcinyle ou aralkyle, X désigne hydrogène, halogène, cycloalkyle ou alkyle éventuellement substitué, alcoxy, alkylthio, alkylamino ou dialkylamino, Y désigne hydrogène, halogène ou alkyle éventuellement substitué, alcoxy, alkylthio, alkylamino ou dialkylamino et Z désigne azote ou le groupement C-R?4, où R4¿ désigne hydrogène, halogène, alkyle ou alcoxy. L'invention concerne également des sels des composés de la formule (I), ainsi que des procédés permettant de préparer les nouveaux composés et leur utilisation comme herbicides.
PCT/EP1994/000138 1993-02-01 1994-01-20 Urees arylaminosulfonyliques Ceased WO1994018177A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU59692/94A AU5969294A (en) 1993-02-01 1994-01-20 Arylaminosulphonyl ureas

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19934302701 DE4302701A1 (de) 1993-02-01 1993-02-01 Arylaminosulfonylharnstoffe
DEP4302701.6 1993-02-01

Publications (1)

Publication Number Publication Date
WO1994018177A1 true WO1994018177A1 (fr) 1994-08-18

Family

ID=6479333

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP1994/000138 Ceased WO1994018177A1 (fr) 1993-02-01 1994-01-20 Urees arylaminosulfonyliques

Country Status (3)

Country Link
AU (1) AU5969294A (fr)
DE (1) DE4302701A1 (fr)
WO (1) WO1994018177A1 (fr)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN103288750A (zh) * 2013-03-04 2013-09-11 盐城工学院 新型氨基磺酰脲类化合物
US12012397B2 (en) 2017-12-18 2024-06-18 NodThera Limited Sulphonyl urea derivatives as NLRP3 inflammasome modulators
US12054461B2 (en) 2019-06-12 2024-08-06 NodThera Limited Sulfonylurea derivatives and uses thereof

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5815962A (ja) * 1981-07-21 1983-01-29 Mitsui Toatsu Chem Inc 新規スルホニルウレイド誘導体
DE3243533A1 (de) * 1981-12-03 1983-06-09 Sandoz-Patent-GmbH, 7850 Lörrach Sulfonamide als herbizide
DE3300569A1 (de) * 1982-01-12 1983-07-21 CIBA-GEIGY AG, 4002 Basel Triaza-verbindungen
EP0264467A1 (fr) * 1984-12-03 1988-04-27 Ppg Industries, Inc. Dérivés sulfamoyl urées
EP0528212A1 (fr) * 1991-08-09 1993-02-24 Bayer Ag N-azinyl-N'-(2-éthylsulfinyl-phénylsulfonyl)urées comme herbicides
EP0528211A1 (fr) * 1991-08-09 1993-02-24 Bayer Ag N-azinyl-N'-(2-méthylsulfinyl-phénylsulfonyl)urées comme herbicides

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5815962A (ja) * 1981-07-21 1983-01-29 Mitsui Toatsu Chem Inc 新規スルホニルウレイド誘導体
DE3243533A1 (de) * 1981-12-03 1983-06-09 Sandoz-Patent-GmbH, 7850 Lörrach Sulfonamide als herbizide
DE3300569A1 (de) * 1982-01-12 1983-07-21 CIBA-GEIGY AG, 4002 Basel Triaza-verbindungen
EP0264467A1 (fr) * 1984-12-03 1988-04-27 Ppg Industries, Inc. Dérivés sulfamoyl urées
EP0528212A1 (fr) * 1991-08-09 1993-02-24 Bayer Ag N-azinyl-N'-(2-éthylsulfinyl-phénylsulfonyl)urées comme herbicides
EP0528211A1 (fr) * 1991-08-09 1993-02-24 Bayer Ag N-azinyl-N'-(2-méthylsulfinyl-phénylsulfonyl)urées comme herbicides

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
PATENT ABSTRACTS OF JAPAN vol. 7, no. 86 (C - 161) 9 April 1983 (1983-04-09) *

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN103288750A (zh) * 2013-03-04 2013-09-11 盐城工学院 新型氨基磺酰脲类化合物
US12012397B2 (en) 2017-12-18 2024-06-18 NodThera Limited Sulphonyl urea derivatives as NLRP3 inflammasome modulators
US12459925B2 (en) 2017-12-18 2025-11-04 NodThera Limited Sulphonyl urea derivatives as NLRP3 inflammasome modulators
US12054461B2 (en) 2019-06-12 2024-08-06 NodThera Limited Sulfonylurea derivatives and uses thereof

Also Published As

Publication number Publication date
AU5969294A (en) 1994-08-29
DE4302701A1 (de) 1994-08-04

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