Classifications

• • A—HUMAN NECESSITIES
  • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
  • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
  • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
  • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
  • A01N47/28—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 the use of special sulfonylureas for the non-selective control of undesired plant growth and for the selective control of undesired plant growth in legumes.
• N-azinyl-N'-arylsulphonylureas are linked to simple open-chain hydroxamic acid ester groups in the aryl moiety, e.g. N- (4,6-
• Dimethylpyrimidin-2-yl) -N '- (2-methoxyaminocarbonyl-phenylsulfonyl) -urea and the corresponding -N' - (2-n-octyloxyaminocarbonylphenylsulfonyl) -urea have herbicidal properties (cf., DE-A-3 516 435, EP -A-173 958, US-4 704 158). However, the herbicidal action of these known compounds is not satisfactory in all respects.
• the object of the present invention was to improve control of undesired plant growth, e.g. also in crops.
• specific compounds of the formula (I) and their salts as agrochemical active ingredients for improved, in particular selective
• the present invention thus relates to the use of compounds of general formula (I) and their salts for the non-selective control of undesirable plant growth or for the selective control of undesired plant growth in legumes wherein
• A is nitrogen or a CR 11 group , where R 11 is hydrogen, alkyl, halogen and haloalkyl,
• R 1 is hydrogen or an optionally substituted radical from the group consisting of alkyl, alkoxy, alkoxyalkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, aralkyl and aryl
• R 2 is hydrogen, halogen or in each case optionally halogen-substituted alkyl, alkoxy, alkylthio, Alkylamino or dialkylamino each having 1 to 6 carbon atoms
• R 3 is hydrogen, halogen or each optionally halogen-substituted alkyl, alkoxy, alkylthio, alkylamino or dialkylamino each having 1 to 6 carbon atoms
• R 4 - R 7 are independently hydrogen , Halogen, cyano, thiocyanato or in each case optionally halogen-substituted alkyl, alkoxy, alkylthio, Alkylsulf ⁇ nyl, alkyl
• the alkyl and alkylene groups each have 1 to 6 C Atoms
• the alkenyl and alkynyl groups each 2 to 6 carbon atoms
• the cycloalkyl groups each 3 to 6 carbon atoms
• the aryl groups may each contain 6 or 10 carbon atoms.
• the invention preferably relates to the use of compounds of the formula (I) and their salts,
• A is nitrogen or a CH group
• R 1 is hydrogen or an optionally halogen-substituted radical from the series alkyl, alkoxy, alkoxyalkyl, alkenyl and alkynyl having in each case up to 3 carbon atoms
• R 2 is hydrogen, halogen or in each case optionally halogen-substituted alkyl, alkoxy, alkylthio, Alkylamino or dialkylamino having in each case 1 to 3 carbon atoms in the alkyl radicals
• R 3 is hydrogen, halogen or each optionally halogen-substituted alkyl, alkoxy, alkylthio, alkylamino or dialkylamino each having 1 to 3 carbon atoms in the alkyl radicals
• R 4 - R 7 is independently of one another hydrogen, halogen, cyano, thiocyanato or in each case optionally halogen-substituted alkyl, alkoxy, alkylthio, alkylsulfin
• the invention further preferably relates to the use of salts which are obtained from compounds of the formula (I) and bases, such as, for example, sodium, potassium or calcium hydroxide, hydride, amide and carbonate, sodium or potassium C 1 -C 4 - Alkoxides, ammonia, -CC 4 -alkylamines, di- (C C4-alkyl) -amines or tri- (-CC 4 - alkyl) -amines, obtained by conventional methods.
• bases such as, for example, sodium, potassium or calcium hydroxide, hydride, amide and carbonate, sodium or potassium C 1 -C 4 - Alkoxides, ammonia, -CC 4 -alkylamines, di- (C C4-alkyl) -amines or tri- (-CC 4 - alkyl) -amines, obtained by conventional methods.
• the invention relates in particular to the use of compounds of the formula (I) and their salts,
• A is nitrogen or a CH group
• R 1 is hydrogen, methyl, ethyl, methoxy, methoxymethyl or ethoxy
• R 2 is hydrogen, chlorine, methyl, ethyl, trifluoromethyl, methoxy, ethoxy, difluoromethoxy, methylthio, methylamino or dimethylamino
• R 3 is hydrogen, chlorine, methyl, ethyl, trifluoromethyl, methoxy, ethoxy, difluoromethoxy, methylthio, methylamino or dimethylamino
• R 4 - R 7 independently of one another represent hydrogen, fluorine, chlorine, cyano, or in each case optionally by chlorine or fluorine is substituted methyl, methylthio, methylsulfinyl, methylsulfonyl, methoxycarbonyl and ethoxycarbonyl, preferably hydrogen
• R 8 is hydrogen, fluorine, chlorine, bromine, cyano or represents in each case optionally substituted by chlorine or fluorine methyl, methoxy, ethoxy, methylthio, ethylthio, methylsulfinyl , Ethylsulfinyl, methylsulfonyl, ethylsulfonyl, methyl or dimethylamino, preferably hydrogen.
• the invention particularly preferably relates to the use of compounds of the formula (I) and their salts, in particular their alkali metal salts,
• A is nitrogen
• R 1 is hydrogen or methyl
• R 2 is hydrogen, chlorine, methyl, ethyl, trifluoromethyl, methoxy, ethoxy, difluoromethoxy, methylthio, methylamino or dimethylamino,
• R 3 is hydrogen, chlorine, methyl, ethyl, trifluoromethyl, methoxy, ethoxy, difluoromethoxy, methylthio, methylamino or dimethylamino
• R 4 - R 7 is hydrogen
• R 8 is hydrogen
• the invention also particularly preferably relates to the use of compounds of the formula (I) and their salts, in particular their alkali metal salts,
• A is a CH group
• R 1 is hydrogen or methyl
• R 2 is hydrogen, chlorine, methyl, ethyl, trifluoromethyl, methoxy, ethoxy, difluoromethoxy, methylthio, methylamino or dimethylamino
• R 3 is hydrogen, chlorine, methyl , Ethyl, trifluoromethyl, methoxy, ethoxy, difluoromethoxy, methylthio, methylamino or dimethylamino
• R 4 - R 7 is hydrogen
• R 8 is hydrogen.
• hydrocarbon radicals mentioned in the radical definitions such as alkyl, alkenyl or alkynyl, even in combinations with heteroatoms, such as in alkoxy, alkylthio, haloalkyl or alkylamino, are, even if not expressly stated, straight-chain or branched.
• Salts may optionally be prepared from the compounds of general formula (I), for example metal salts such as alkali (eg Na, K) salts or alkaline earth metals (eg Ca, Mg) salts or ammonium or amine salts.
• metal salts such as alkali (eg Na, K) salts or alkaline earth metals (eg Ca, Mg) salts or ammonium or amine salts.
• 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 diluent, for example methylene chloride, acetone, tert-butyl methyl ether or toluene, and adding a suitable base.
• the salts can then - be isolated by concentration or suction - optionally after prolonged stirring.
• (+) The indicated melting point (mp) refers in each case to the corresponding sodium salt, ie the corresponding compound in which the hydrogen of the -SO 2 -NH group has been replaced by sodium.
• the compounds of formula (I) and their salts can be used to control undesired plant growth.
• Undesirable plants are understood to mean all plants that grow in places where they are undesirable. This can e.g. Harmful plants (e.g., weeds or unwanted crops), e.g. also those which are resistant to certain herbicidal active substances such as glyphosate, atrazine, glufosinate or imidazolinone herbicides.
• the compounds of formula (I) may e.g. used against the following plants:
• Monocotyledonous weeds eg of the genera Echinochloa, Setaria, Panicum, Digitaria, Phleum, Poa, Festuca, Eleusine, Brachiaria, Lolium, Bromus, Avena, Cyperus, Sorghum, Agropyron, Cynodon, Monochoria, Fimbristylis, Sagittaria, Eleocharis, Scirpus, Paspalum, Ischemum, Sphenociea, Dactyloctenium, Agrostis, Alopecurus, Apera.
• Dicotyledonous weeds eg 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,
• Monocotyledonous crops e.g. monocots transgenic and non-transgenic crops, e.g. of the genera Oryza, Zea, Triticum, Hordeum, Avena, Secale, Sorghum, Panicum, Saccharum, Pineapple, Asparagus, Allium.
• Dicotyledonous crops e.g. of the genera Gossypium, Beta, Solanum, Nicotiana, Lycopersicon, Brassica, Lactuca, Cucumis, Cucurbita.
• the compounds of formula (I) and their salts have excellent selectivity in legume crops. They are suitable, e.g. for the selective control of undesired plant growth, e.g. of harmful plants (for example monocotyledonous and dicotyledonous weeds or undesired crop plants), in cultures of transgenic and non-transgenic legumes, in particular of the genus Glycine, for example in the pre-sowing, pre-emergence or postemergence process.
• harmful plants for example monocotyledonous and dicotyledonous weeds or undesired crop plants
• legumes come e.g. transgenic and non-transgenic legumes, e.g. of the genera Glycine, Phaseolus, Pisum, Vicia and Arachis in question.
• legumes of the genus Glycine are suitable, e.g. of the type Glycine max.
• Cultivated crops e.g. monocotyledonous crops such as cereals (e.g., wheat, barley, rye, oats), rice, corn, millet, or dicotyledonous crops such as sugar beet, oilseed rape, cotton, sunflowers, and legumes, e.g. of the genera Glycine (eg Glycine max. (soy) as non-transgenic Glycine max (eg conventional varieties such as STS varieties) or transgenic Glycine max (eg RR soy or LL soy) and their crosses), Phaseolus, Pisum , Vicia and Arachis, or vegetable crops from various botanical groups such as potato, leek, cabbage, carrot, tomato, onion.
• the application is preferably carried out on the accumulated harmful plants (for example weeds or undesired crop plants), in particular before emergence of the (desired) crop plants.
• a preferred use in the non-selective area is the burn-down application in crops, wherein the compounds of formula (I) and their salts are applied to the accrued harmful plants before emergence of the crop plants, preferably the application before sowing the Crops or when sowing the crops.
• the compounds of the formula (I) and salts thereof can be converted into customary formulations, such as solutions, emulsions, suspensions, powders, foams, pastes, granules, aerosols, active substance-impregnated natural and synthetic substances, microencapsulations in polymeric substances.
• the formulations may contain the usual auxiliaries and additives. These formulations are prepared in a known manner, for example by mixing the active compounds with extenders, ie liquid solvents, liquefied gases under pressure and / or solid carriers, optionally with the use of surface-active agents, ie emulsifiers and / or dispersants and / or foam-forming agents.
• Suitable liquid solvents are essentially: aromatics, such as xylene, toluene, alkylnaphthalenes, chlorinated aromatics or 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 or 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 or dimethyl sulfoxide, and water.
• Suitable solid carriers are: e.g. 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; suitable solid carriers for granules are: 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, alkylsulfates, arylsulfonates and protein hydrolysates; suitable dispersants are: e.g. Ligninsulfitablaugen and methylcellulose.
• adhesives such as carboxymethylcellulose, natural and synthetic, powdery, granular or latex-like polymers are used, 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.
• 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.
• the formulations generally contain between 0.1 and 95% by weight of active ingredient, preferably between 0.5 and 90%.
• the active compounds of the formula (I) and their salts may also be used as such or in their formulations in admixture with other agrochemical active substances such as known herbicides for controlling undesired plant growth, e.g. for weed control or to control undesirable crops, e.g. Ready-to-use formulations or tank mixes are possible.
• agrochemical active substances such as known herbicides for controlling undesired plant growth, e.g. for weed control or to control undesirable crops, e.g. Ready-to-use formulations or tank mixes are possible.
• known agrochemical active substances can be used, as are described in, for example, US Pat. Weed Research 26, 441-445 (1986), or "The Pesticide Manual", 13th edition, The British Crop Protection Council, 2003, and references cited therein.
• Stereoisomers and optical isomers One and in part also several application forms are mentioned): 2,4-D, acetochlor, acifluorfen, acifluorfen-sodium, aclonifen, alachlor, alloxydim, alloxydim-sodium, ametryn, amicarbazone, amidosulfuron, aminopyralid, amitrole, anilofos, asulam, atrazine, azafenidine, azimsulfuron, beflubutamide, benazoline, benazoline ethyl, benfuresate, bensulfuron-methyl, bentazone, benzofendizone, benzobicyclone, benzofenap, bifenox, bilanafos, bispyribac-sodium, bromacil, bromobutides, bromofenoxime, bromoxynil, butachlor, butafenacil, butenachlor, butraline, butr
• Fluorochloridones fluoroglycofen-ethyl, flupoxam, flupyrsulfuron-methyl-sodium, fluridone, fluroxypyr, fluroxypyr-butoxypropyl, fluroxypyr-meptyl, flurprimidol, flurtamone, fluthiacet-methyl, fomesafen, foramsulfuron, glufosinate, glufosinate-ammonium, glyphosate, halosulfuron-methyl, Haloxyfop, haloxyfopethoxyethyl, haloxyfopmethyl, haloxyfop-P-methyl, hexazinone, imazamethabenz-methyl,
• Suitable combination partners are preferably compounds which are selective in soy, for example
• (Ba) selective herbicides effective in soybean monocotyledonous and dicotyledonous harmful plants for example trifluralin, metribuzin, clomazone, pendimethalin, metolachlor, flumetsulam, dimethenamid, linuron, ethalfluralin, flufenacet, norflurazon, vernolates, chlorotoluron, chlorotoluron, cloransulam and esters such as the methyl ester; Imazethapyr, Imazamox, Imazaquin,
• non-selective e.g. also for specific purposes in soybean usable herbicides, eg. Glufosinate, glyphosate, paraquat (salts) such as paraquat dichloride,
• Also preferred combination partners are Benozalin, Fenoxaprop, Lactofen, Chlortoluron, Flufenacet, Metribuzin, Benfuresate, Fentrazamide, Mefenacet, Diclofop, loxynil, Bromoxynil, Amidosulfuron, Flurtamone, Diflufenican, Ethoxysulfuron, Flucarbazone, Propoxycarbazone, Sulcotrione, Mesotrione,
• Isoproturon lodosulfuron, mesosulfuron, foramsulfuron, anilofos, oxaziclomefones, oxadiargyl, isoxaflutole, linuron.
• the active compounds of the formula (I) and salts thereof 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 present invention further relates to a method for controlling undesired plant growth (eg for non-selective control of harmful plants or for selective control of harmful plants in legumes), wherein one or more compounds of the formula (I) and their Salts on the plants (eg harmful plants such as monocotyledonous or dicotyledonous weeds or unwanted crops), the seed (eg grains, seeds or vegetative propagules such as tubers or sprouts with buds) or the area on which the plants grow (eg the acreage) are applied , They can be applied, for example, before sowing, as well as before and after emergence of the plants.
• the pre-seed application can be done, for example, by spraying or incorporation into the soil. Also split applications eg in early pre-emergence followed by later postemergence application are possible. Preference is given to an application to the accumulated harmful plants, in particular before emergence of (desired) crops such as legumes.
• Preferred for selective use in legumes is application to crops, especially to emerged weeds (e.g., weeds or unwanted crops), preferably prior to legume emergence.
• Preferred for non-selective use is application to the emergent weeds (e.g., weeds or undesirable crops).
• In the burn-down application is preferably applied before sowing or sowing the crops on the accumulated harmful plants.
• the amount of active ingredient used can vary within a substantial range. It depends essentially on the type of effect desired.
• the application rates are between 0.01 g and 100 g of active ingredient per hectare of soil.
• For a selective application are generally lower application rates, for example in the range of 0.01 g to 9 g of active ingredient per hectare, preferably between 0.1 g and 5 g per hectare, especially in the application to accumulated plants, especially on accrued harmful plants (eg, weeds or unwanted crops).
• the active compounds of the formula (I) and their salts have an excellent selectivity in legumes, and surprisingly, even at low doses of active ingredient, an outstanding action against the harmful plants typically occurring in leguminous plants is maintained.
• leguminous crops often difficult to control, such as species of the genera Amaranthus, Echinochloa, Sorghum, Ipomoea, Pharbitis, Solanum, Setaria, Brachiaria, Lolium, Euphorbia, Abutilon are effectively combated.
• the compounds have an excellent effect in non-selective application, e.g. in permanent and plantation crops or on roadsides, squares, industrial plants, airfields or railway facilities or in the burn-down application.
• Seeds or rhizome pieces of monocotyledonous and dicotyledonous weed plants were placed in sandy soil in cardboard pots and covered with soil.
• the formulated in the form of wettable powders or emulsion concentrates compounds of formula (I) or salts thereof were then applied as aqueous suspensions or emulsions with a water application rate of 600 to 800 l / ha in different dosages on the surface of the cover soil.
• the pots were placed in the greenhouse and kept under good growth conditions for the weeds.
• the optical assessment of the plant damage and / or the emergence damage occurred after emergence of the test plants after a test time of 3 to 4 weeks in comparison to untreated controls.
• the compounds tested have good herbicidal pre-emergence activity against a broad spectrum of grass weeds and weeds. For example, compounds Nos.
• Seeds or rhizome pieces of monocotyledonous and dicotyledonous weeds were placed in sandy loam soil in plastic pots, covered with soil and grown in the greenhouse under good growth conditions. Three weeks after sowing, the test plants were treated at the trefoil stage.
• the compounds of the formula (I) or salts thereof formulated as wettable powders or as emulsion concentrates were sprayed onto the green plant parts in various dosages with a water application rate of 600 to 800 l / ha. After about 3 to 4 weeks of life of the test plants in the greenhouse under optimal growth conditions, the effect of the preparations was optically scored compared to untreated controls.
• the tested compounds also have a post-emergence good herbicidal activity against a broad spectrum of economically important weeds and weeds.
• compounds Nos. 1-1, I-3, I-8, I-9, 1-10, 1-11, 1-12, 1-14, I-21, I-22, I-23, 1-29, I-30, 1-51, I-52, 1-60, 1-70, 1-142, 1-143, 1-145 and other compounds of Table 1 have very good herbicidal activity against harmful plants such as Sinapis alba , Echinochloa crus-galli, Lolium multiflorum, Chrysanthemum segetum, Setaria viridis, Abutilon theophrasti, Amaranthus retroflexus, Panicum miliaceum, Brachiaria plantaginea, Solanum nigrum, Euphorbia heterophylla, Sorghum halepense and Avena sativa postemergence at an application rate of 100 g and less active substance per hectares.
• connection shows 1-9 at an application rate of 30 g of active ingredient per hectare herbicidal action of 100% against Echinochloa crus galli, of 100% compared to Brachiaria plantaginea, of 100% compared to Setaria viridis, of 93% Amaranthus retroflexus and of 100% compared to Solanum nigrum.

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• 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)
• Plural Heterocyclic Compounds (AREA)
• Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
• Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)

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