WO2011039276A1 - Oxathiazinyl-(hétéro) arylsulfonylurées, procédé et produits intermédiaires pour leur préparation et leur utilisation en tant que pesticides et régulateurs de croissance des plantes - Google Patents

Oxathiazinyl-(hétéro) arylsulfonylurées, procédé et produits intermédiaires pour leur préparation et leur utilisation en tant que pesticides et régulateurs de croissance des plantes Download PDF

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WO2011039276A1
WO2011039276A1 PCT/EP2010/064493 EP2010064493W WO2011039276A1 WO 2011039276 A1 WO2011039276 A1 WO 2011039276A1 EP 2010064493 W EP2010064493 W EP 2010064493W WO 2011039276 A1 WO2011039276 A1 WO 2011039276A1
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ppm
formula
hydrogen
halogen
alkyl
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PCT/EP2010/064493
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German (de)
English (en)
Inventor
Ulrich Philipp
Guido Bojack
Christopher Hugh Rosinger
Dieter Feucht
Isolde HÄUSER-HAHN
Jan Dittgen
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Bayer Cropscience Ag
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Publication of WO2011039276A1 publication Critical patent/WO2011039276A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D419/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen, oxygen, and sulfur atoms as the only ring hetero atoms
    • C07D419/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen, oxygen, and sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D419/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen, oxygen, and sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
    • 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
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D419/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen, oxygen, and sulfur atoms as the only ring hetero atoms
    • C07D419/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen, oxygen, and sulfur atoms as the only ring hetero atoms containing three or more hetero rings

Definitions

  • A is nitrogen or a CR moiety
  • R 11 is hydrogen, alkyl, halogen and haloalkyl
  • R 1 is hydrogen or an optionally substituted radical from the series alkyl, alkoxy, alkoxyalkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, aralkyl and
  • R 2 is hydrogen, halogen or each optionally halogen
  • R 3 is hydrogen, halogen or each optionally halogen
  • J is J-1 to J-4, wherein J-1 to J-4 have the following meanings:
  • the arrow is in each case a bond to the sulfonyl unit of the formula (I), represents a direct bond, alkylene, oxygen, alkylamino or sulfur,
  • alkyl independently of one another are hydrogen, halogen, cyano, thiocyanato or in each case optionally halogen-substituted alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylamino, alkylcarbonyl,
  • Cycloalkyl groups each 3 to 6 carbon atoms and the aryl groups may each contain 6 or 10 carbon atoms, as well as salts of compounds of formula (I) found.
  • a characteristic structural feature of the new sulfonylureas (I) is therefore the (5,6-dihydro- [1,2,2] oxathiazin-3-yl) radical as a novel heterocyclic substituent in the (het) aryl portion of the (het) arylsulfonylureas.
  • the simple body of this class of compounds such.
  • the (5,6-dihydro- [1, 4.2] -oxathiazin-3-yl) benzene, - thiazole or pyridine are known (see, Brouwer, W.G., Blem, A. R. et al., EP
  • R 1 to R 3 have the meanings given above and
  • R 12 is alkyl or aryl
  • a and R to R have the meanings given above, if appropriate in the presence of a diluent and if appropriate in the presence of a reaction auxiliary, or if
  • a and R 1 to R 3 have the meanings given above, if appropriate in the presence of a diluent and if appropriate in the presence of a reaction auxiliary, and, if appropriate, the products obtained by processes (a), (b) or (c) are converted into salts by customary methods.
  • the new oxathiazinyl (het) arylsulfonylureas of the formula (I) are distinguished by their strong herbicidal activity.
  • novel compounds of the formula (I) show considerably greater activity and / or increased selectivity than the compounds which are comparable in structure and activity profile N- (4,6-dimethylpyrimidin-2-yl) -N '- (2-methoxyaminocarbonyl-phenylsulfonyl ) urea and the corresponding -N '- (2-n-octyloxyaminocarbonyl-phenylsulfonyl) urea or dihydro-dioxazines as described in EP 0645386A1 (US 5476936).
  • the invention preferably compounds
  • 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, each with up to
  • R 2 is hydrogen, halogen or each optionally halogen
  • R 3 is hydrogen, halogen or each optionally halogen
  • J is J-1 to J-4, preferably J-2,
  • R 4 -R 7 independently of one another represent hydrogen, halogen, cyano, thiocyanato or in each case optionally halogen-substituted alkyl, alkoxy,
  • R 8 is hydrogen or an optionally substituted radical from the series (dC 4) -alkyl, (C 3 -C 6) -cycloalkyl, (C 7 -CN) aralkyl and (C 6 -C 0) aryl, R 10 independently of one another represent hydrogen, halogen, cyano, thiocyanato or in each case optionally halogen-substituted alkyl, alkoxy,
  • Alkoxycarbonyl or alkylaminocarbonyl each having 1 to 3
  • the invention further preferably relates to 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 ) -alkanolaten, ammonia, (Ci-C 4) - alkyl amines, di - ((Ci-C 4) -alkyl) amines or tri - ((Ci-C 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 ) -alkanolaten, ammonia, (Ci-C 4) - alkyl amines, di - ((Ci-C 4) -alkyl) amines or tri - ((Ci-C 4) alkyl) -amines, obtained by conventional methods.
  • the invention particularly relates to compounds of the formula (I)
  • 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
  • R 3 is hydrogen, chlorine, methyl, ethyl, trifluoromethyl, methoxy, ethoxy,
  • J is J-1 to J-4, preferably J-2,
  • R 4 -R 7 independently of one another represent hydrogen, fluorine, chlorine, cyano, or in each case optionally substituted by chlorine or fluorine, methyl, methylthio, methylsulfinyl, methylsulfonyl, methoxycarbonyl and ethoxycarbonyl,
  • R 8 is hydrogen, methyl, ethyl, phenyl or benzyl
  • R 10 is independently of one another hydrogen, fluorine, chlorine, bromine, cyano or in each case optionally substituted by chlorine or fluorine methyl, methoxy, ethoxy, methylthio, ethylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl, ethylsulfonyl, methyl or dimethylamino.
  • Residue definitions apply both to the end products of the formula (I) and correspondingly to the starting or end preparation required in each case.
  • hydrocarbon radicals mentioned in the radical definitions such as alkyl, alkenyl or alkynyl, even in combinations with heteroatoms, such as in alkoxy, alkylthio or alkylamino, are also straight-chain or branched, even if not expressly stated.
  • Examples of the compounds of the formula (II) which may be mentioned are: 2- (5,6-dihydro [1,2,2] oxathiazin-3-yl) benzenesulfonamide, 2- (5,6-dihydro- [1, 4 , 2] -oxathiazin-3-yl) -6-methyl-benzenesulfonamide, 2- (5,6-dihydro- [1,2,2] -oxathiazin-3-yl) -phenylmethanesulfonamide, 3- (5,6- Dihydro- [1,2,2] oxathiazin-3-yl) -pyridine-2-sulfonamide, 2- (5,6-dihydro- [1,2,2] -oxathiazin-3-yl) -thiophene-3 sulfonamide, 1-methyl-4- (5,6-dihydro- [1,2,2] oxathiazin-3-yl) -pyrazole
  • N-azinyl carbamates also to be used as starting materials in process (a) are generally defined by formula (III).
  • A, R 1 , R 2 and R 3 preferably or in particular have those meanings which have already been mentioned above in connection with the description of the novel compounds
  • R 12 is preferably (C 1 -C 6) -alkyl or (C 1 -C 5) -aryl, particularly preferably (C 1 -C 4 ) -alkyl or phenyl.
  • the starting materials of the formula (III) are known and / or can be prepared by processes known per se (cf., EP-238 070).
  • Examples of starting materials of the formula (IV) which may be mentioned are: 2- (5,6-dihydro- [1,2,2] oxathiazin-3-yl) benzenesulfonyl isocyanate, 2- (5,6-dihydro- [1, 4,2] -oxathiazin-3-yl) -6-methyl-benzenesulfonyl isocyanate, 2- (5,6-dihydro- [1,2,2] -oxathiazin-3-yl) -phenylmethanesulfonyl isocyanate, 3- (5,6- Dihydro- [1,2,2] oxathiazin-3-yl) -pyridine-2-sulfonyl isocyanate, 2- (5,6-dihydro- [1,2,2] oxathiazin-3-yl) -thiophene-3 sulfonyl isocyanate, 1-methyl-4- (5,6-dihydro-
  • the starting materials of the formula (IV) are not yet known from the literature and as novel substances are also the subject of the present invention.
  • the novel (het) arylsulfonyl isocyanates of the formula (IV) are obtained by reacting (het) arylsulfonamides of the above formula (II) with phosgene in the presence of a diluent, such as, for example, chlorobenzene, and reaction auxiliaries, such as, for example, butyl isocyanate and diazabicyclooctane (DABCO), at temperatures between 0 ° C and 200 ° C, preferably between 20 ° C and 160 ° C, and then the volatile components are carefully distilled off under reduced pressure (see, EP 162 723).
  • a diluent such as, for example, chlorobenzene
  • reaction auxiliaries such as, for example, butyl isocyanate and diazabicyclooctane (DABCO)
  • formula (V) The in process (b) for the preparation of compounds of formula (I) further required as starting materials aminoazines are generally defined by formula (V).
  • A, R 1 , R 2 and R 3 are preferably or
  • the starting materials of the formula (V) are known and / or can be prepared by processes known per se (compare Huaxue Shijie, 32 (6), 254-7 (1991) JP-01 016 770, EP-246 984); some of these substances are commercially available synthetic chemicals.
  • a diluent e.g. Dioxane or acetone itril
  • reaction auxiliaries e.g. Pyridine, potassium or calcium carbonate
  • (het) arylcarboxyimidoyl chlorides are generally defined by formula (VIII).
  • the group J preferably has those
  • the starting materials of the formula (VIII) are all known, some commercially available aldehydes, which can be converted by means of hydroxylamine first in their Carbaldoxime and then with chlorinating agents such as N-chlorosuccinimide or gaseous chlorine in the compounds of formula (VIII) ,
  • chlorinating agents such as N-chlorosuccinimide or gaseous chlorine in the compounds of formula (VIII)
  • the new (het) arylsulfonamides of the formula (II) are obtained if (d) N-hydroxy- (het) arylcarboxyimidoyl chlorides of the formula (VIII)
  • Y is hydrogen or halogen (preferably hydrogen or bromine)
  • R 4 - R 7 have the meanings given above, if appropriate in the presence of an organic diluent and if appropriate in the presence of a reaction auxiliary.
  • Suitable reagents for a cyclization are dialkyl azodicarboxylates in combination with triphenylphosphine and nitrophenols as catalyst (Mitsunobu conditions, see also Kai, Nakai Tetrahedron Lett., 42 (2001) 6895-6897)
  • Y is hydrogen or halogen (preferably hydrogen or bromine)
  • R 4 - R 7 have the meanings given above, where X is halogen
  • Organometallic compounds such as e.g. n-butyllithium, n-butylmagnesium chloride, n-butylmagnesium bromide, sec-butyllithium or tert-butyllithium, in the course of a halogen-metal exchange or e.g. with n-butyllithium, n-butylmagnesium chloride, n-butylmagnesium bromide, sec-butyllithium, tert-butyllithium,
  • Sulfonylating agents such as gaseous sulfur dioxide on their Metal sulfinates, which are then oxidized with sulfuryl chloride, or directly with sulfuryl chloride in the chlorosulfones are transferred.
  • the chlorosulfones can then be treated with a suitable nitrogen source, e.g. gaseous ammonia or aqueous ammoniacal solutions into the desired compounds of formula (II).
  • a suitable nitrogen source e.g. gaseous ammonia or aqueous ammoniacal solutions into the desired compounds of formula (II).
  • Suitable diluents are virtually all inert organic solvents. These include
  • Hydrocarbons such as pentane, hexane, heptane, cyclohexane, petroleum ether, gasoline, ligroin, benzene, toluene, xylene, methylene chloride,
  • Chlorobenzene and o-dichlorobenzene ethers such as diethyl and dibutyl ether,
  • ketones such as acetone, methyl ethyl, methyl isopropyl and methyl isobutyl ketone
  • esters such as methyl acetate and ethyl acetate
  • nitriles such as e.g. Acetonitrile and propionitrile
  • amides e.
  • the processes (a), (d) and (e) according to the invention are optionally carried out in the presence of a reaction auxiliary.
  • a reaction auxiliary preferably include basic organic nitrogen compounds, e.g. Trimethylamine, triethylamine, N, N-dimethylaniline, ⁇ , ⁇ -dimethylbenzylamine, pyridine, 4-dimethylaminopyridine, diazabicyclooctane (DABCO), diazabicyclononene (DBN) and diazabicycloundecene (DBU), as well as inorganic bases, e.g. Sodium hydride, potassium hydride,
  • inventive processes (b) and (c) are optionally carried out in the presence of a reaction auxiliary.
  • a reaction auxiliary Suitable for this purpose are preferably basic organic nitrogen compounds, e.g. Trimethylamine, triethylamine, N, N-dimethylaniline, ⁇ , ⁇ -dimethylbenzylamine, pyridine, N, N-dimethylaminopyridine, diazabicyclooctane (DABCO), diazabicyclononene (DBN) and diazabicycloundecene (DBU).
  • DABCO diazabicyclooctane
  • DBN diazabicyclononene
  • DBU diazabicycloundecene
  • reaction temperatures can in each case be varied within a relatively wide range in processes (a) to (e).
  • - in process (c) also generally at temperatures between 0 ° C and 150 ° C, preferably so at temperatures between 20 ° C and 100 ° C;
  • + 40 ° C preferably at temperatures between -20 ° C and + 30 ° C.
  • the processes (a) to (e) are generally carried out under normal pressure. However, it is also possible to work under increased or reduced pressure.
  • the particular starting materials required in each case are 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 and optionally with the addition of a reaction auxiliary, and the reaction mixture becomes several
  • 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 the formula (I) in a suitable manner
  • Diluents such as methylene chloride, acetone, tert-butyl methyl ether or toluene, and addition of a suitable base.
  • the salts can then be isolated by concentrating or filtering off, if appropriate after prolonged stirring (compare the preparation examples).
  • the active compounds according to the invention can be used as defoliants, desiccants, haulm killers and especially 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 essentially depends on the amount used.
  • the active compounds of the invention may e.g. used in the following plants:
  • Echinochloa Setaria, Panicum, Digitaria, Phleum, Poa, Festuca, Eleusine,
  • 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. Forest, ornamental, fruit, wine, citrus, nut, banana, coffee, tea, gum, oil palm, cocoa, berry fruit and hop plants, on ornamental and sports turf and pasture and selective Weed control in one-year crops.
  • the compounds of the formula (I) according to the invention are suitable for the selective control of monocotyledonous and dicotyledonous weeds in different crops, in part e.g. in wheat, both pre-emergence and post-emergence.
  • the compounds of the invention may be in the form of wettable powders, emulsifiable concentrates, sprayable solutions, dusts or
  • Granules are used in the usual preparations.
  • the invention therefore also relates to herbicidal and plant growth-regulating agents which contain the compounds according to the invention.
  • the compounds according to the invention can be formulated in various ways, depending on which biological and / or chemical-physical parameters are predetermined. As formulation options come
  • wettable powder WP
  • water-soluble powder SP
  • EC emulsifiable concentrates
  • EW emulsions
  • SC Suspension concentrates
  • CS capsule suspensions
  • DP dusts
  • mordants granules for litter and soil application
  • granules GR
  • WG water-dispersible granules
  • SG water-soluble granules
  • the necessary formulation auxiliaries such as inert materials, surfactants,
  • Solvents and other additives are also known and are described, for example, in Watkins, Handbook of Insecticides Dust Diluents and Carriers, 2nd ed., Darland Books, Caldwell N.J., H.v. Olphen, "Introduction to Clay Colloid Chemistry”; 2nd Ed., J. Wiley & Sons, N.Y .; C. Marsden, “Solvents Guide”; 2nd Ed., Interscience, N.Y. 1963; McCutcheon's "Detergents and Emulsifiers
  • Injectable powders are preparations which are uniformly dispersible in water and contain surfactants of the ionic and / or nonionic type (wetting agents, dispersants) in addition to the active ingredient except a diluent or inert substance.
  • surfactants of the ionic and / or nonionic type (wetting agents, dispersants) in addition to the active ingredient except a diluent or inert substance.
  • lignosulfonic acid sodium 2,2'-dinaphthylmethane-6,6'-disulfonic acid sodium, dibutylnaphthalene-sulfonic acid sodium or oleoylmethyltaurine acid.
  • herbicidal active ingredients for example, finely ground in conventional equipment such as hammer mills, blower mills and air jet mills and at the same time or subsequently with the herbicidal active ingredients for example, finely ground in conventional equipment such as hammer mills, blower mills and air jet mills and at the same time or subsequently with the herbicidal active ingredients for example, finely ground in conventional equipment such as hammer mills, blower mills and air jet mills and at the same time or subsequently with the herbicidal active ingredients for example, finely ground in conventional equipment such as hammer mills, blower mills and air jet mills and at the same time or subsequently with the herbicidal active ingredients for example, finely ground in conventional equipment such as hammer
  • Emulsifiable concentrates are prepared by dissolving the active ingredient in an organic solvent, e.g. Butanol, cyclohexanone, dimethylformamide, xylene or higher-boiling aromatics or hydrocarbons or mixtures of organic solvents with the addition of one or more surfactants of ionic and / or nonionic type (emulsifiers).
  • organic solvent e.g. Butanol, cyclohexanone, dimethylformamide, xylene or higher-boiling aromatics or hydrocarbons or mixtures of organic solvents
  • surfactants of ionic and / or nonionic type emulsifiers
  • suitable emulsifiers are: alkylarylsulfonic acid calcium salts such as calcium dodecylbenzenesulfonate or nonionic emulsifiers such as
  • Fatty acid polyglycol esters alkylaryl polyglycol ethers, fatty alcohol polyglycol ethers, propylene oxide-ethylene oxide condensation products, alkyl polyethers, sorbitan esters such as e.g. Sorbitan fatty acid esters or polyoxethylenesorbitan esters such as e.g.
  • Dusts are obtained by milling the active ingredient with finely divided solids, e.g. Talc, natural clays such as kaolin, bentonite and pyrophyllite, or diatomaceous earth.
  • finely divided solids e.g. Talc, natural clays such as kaolin, bentonite and pyrophyllite, or diatomaceous earth.
  • Suspension concentrates may be water or oil based. They can be prepared, for example, by wet grinding using commercially available bead mills and, if appropriate, addition of surfactants, as described, for example, in US Pat. upstairs with the others
  • Emulsions e.g. Oil-in-water emulsions (EW) can be prepared, for example, by means of stirrers, colloid mills and / or static mixers using aqueous organic solvents and optionally surfactants, as described e.g. listed above for the other formulation types.
  • EW Oil-in-water emulsions
  • Granules can be prepared either by spraying the active ingredient on adsorptive, granulated inert material or by applying Active substance concentrates by means of adhesives, for example polyvinyl alcohol, sodium polyacrylate or mineral oils, on the surface of carriers such as sand, kaolinites or granulated inert material. It is also possible to granulate suitable active ingredients in the manner customary for the production of fertilizer granules, if desired in admixture with fertilizers.
  • adhesives for example polyvinyl alcohol, sodium polyacrylate or mineral oils
  • Water-dispersible granules are generally prepared by the usual methods such as spray drying, fluidized bed granulation, plate granulation, mixing with high-speed mixers and extrusion without solid inert material.
  • the agrochemical preparations generally contain from 0.1 to 99% by weight, in particular from 0.1 to 95% by weight, of compounds according to the invention.
  • the drug concentration is e.g. about 10 to 90 wt .-%, the balance to 100 wt .-% consists of conventional formulation ingredients.
  • the active ingredient concentration may be about 1 to 90, preferably 5 to 80 wt .-%.
  • Dust-like formulations contain 1 to 30 wt .-% of active ingredient, preferably usually 5 to 20 wt .-% of active ingredient, sprayable solutions contain about 0.05 to 80, preferably 2 to 50 wt .-% of active ingredient.
  • the active ingredient content depends, in part, on whether the active compound is liquid or solid and which
  • Granulation aids, fillers, etc. are used. In the water
  • the content of active ingredient is, for example, between 1 and 95% by weight, preferably between 10 and 80% by weight.
  • the active substance formulations mentioned optionally contain the customary adhesion, wetting, dispersing, emulsifying, penetrating, preserving, antifreeze and solvent, fillers, carriers and dyes, antifoams,
  • a dust is obtained by mixing 10 parts by weight of a compound of formula (I) and / or salts thereof and 90 parts by weight of talc as an inert material and comminuted in a hammer mill.
  • a wettable powder readily dispersible in water is obtained by reacting 25 parts by weight of a compound of the formula (I) and / or its salts,
  • a dispersion concentrate readily dispersible in water is obtained by reacting 20 parts by weight of a compound of the formula (I) and / or salts thereof with 6 parts by weight of alkylphenol polyglycol ether ( ⁇ Triton X 207), 3
  • isotridecanol polyglycol ether 8 EO
  • paraffinic mineral oil oil range, for example, about 255 to more than 277 C
  • An emulsifiable concentrate is obtained from 15 parts by weight of a
  • Nonylphenol as emulsifier A water-dispersible granule is obtained by reacting 75 parts by weight of a compound of the formula (I) and / or salts thereof,
  • a water-dispersible granule is also obtained by
  • the active compounds according to the invention can be used as such or in their formulations also in mixture with known herbicides for controlling weeds, ready-to-use formulations or tank mixes being possible.
  • known herbicides for controlling weeds ready-to-use formulations or tank mixes being possible.
  • Active substances which are based on an inhibition of, for example, acetolactate synthase, acetyl-CoA carboxylase, cellulose synthase, enolpyruvylshikimate-3-phosphate synthase, glutamine synthetase, p-hydroxyphenylpyruvate dioxygenase, phytoene desaturase, photosystem I, photosystem II, protoporphyrinogen Oxidase based, for example, as described in Weed Research 26 (1986) 441 -445 or "The Pesticide Manual", 14th edition, The British Crop Protection Council and the Royal Soc. of Chemistry, 2003 and cited there literature are described.
  • Known herbicides or plant growth regulators which can be combined with the compounds according to the invention are, for example, the following active substances (which
  • Flucetosulfuron Fluchloralin, Flufenacet (Thiafluamide), Flufenpyr, Flufenpyr-ethyl, Flumetralin, Flumetsulam, Flumiclorac, Flumiclorac-pentyl, Flumioxazin,
  • indaziflam indoleacetic acid (IAA), 4-indol-3-yl-butyric acid (IBA), iodosulfuron, iodosulfuron-methyl-sodium, loxynil, lecarbarbazonejsocarbamide, isopropalin, isoproturon, isourone, isoxaben, isoxachlortole, isoxaflutole, isoxapyrifop, IDH-100, KUH 043, KUH-071, carbutilates, ketospiradox, lactofen, lenacil, linuron,
  • Nonanoic acid pendimethalin, pendralin, penoxsulam, pentanochlor, pentoxazone, perfluidone, pethoxamide, phenisopham, phenmedipham, phenmedipham-ethyl,
  • CDEC compact disc sulfentrazone, sulfometuron, sulfometuron-methyl, sulfosate (glyphosate trimesium), sulfosulfuron, SYN-523, SYP-249, SYP-298, SYP-300, tebutam, tebuthiuron, tecnazene, tefuryltrione, tembotrione, tepraloxydim, terbacil , Terbucarb, Terbuchlor, Terbumetone, Terbuthylazine, Terbutryn, TH-547, Thenylchloro, thiafluamides, thiazafluron, thiazopyr, thidiazimine, thidiazuron, thiencarbazones, thiencarbazone-n-ethyl, thifensulfuron, thifensulfuron-n-ethyl, thio
  • Insecticides Insecticides, acaricides, nematicides, bird repellents,
  • Plant nutrients and soil conditioners are possible.
  • the compounds according to the invention can also be used in combination with one or more compounds which act as safeners.
  • the safeners are preferably selected from the group consisting of S1) compounds of the formula (S1),
  • n A is a natural number from 0 to 5, preferably 0 to 3;
  • R A 1 is halogen, (C 1 -C 4 ) -alkyl, (C 1 -C 4 ) -alkoxy, nitro or (C 1 -C 4 ) -haloalkyl;
  • W A is an unsubstituted or substituted divalent heterocyclic radical from the group of the unsaturated or unsaturated five-membered ring heterocycles having 1 to 3 hetero ring atoms from the group N and O, wherein at least one N atom and at most one O atom is contained in the ring, preferably a radical from the group (W A 1 ) to (W A 4 ),
  • R A 2 is OR A 3 , SR A 3 or NR A 3 R A 4 or a saturated or unsaturated 3- to 7-membered heterocycle having at least one N atom and up to 3 hetero atoms, preferably from the group O and S, who uses the N atom with the Carbonyl group in (S1) is connected and unsubstituted or by radicals from the group (Ci-C 4 ) alkyl, (dC 4 ) alkoxy or optionally
  • substituted phenyl preferably a radical of the formula ORA 3 , NHR a 4 or N (CH 3 ) 2, in particular of the formula ORA 3 ;
  • R a 3 is hydrogen or an unsubstituted or substituted aliphatic
  • Hydrocarbon radical preferably having a total of 1 to 18 carbon atoms
  • R A 4 is hydrogen, (C 1 -C 6) -alkyl, (C 1 -C 6) -alkoxy or substituted or
  • R A 5 is H, (C 1 -C 8 ) -alkyl, (C 1 -C 8 ) -haloalkyl, (C 1 -C 4 ) -alkoxy- (C 1 -C 8 ) -alkyl, cyano or COORA 9 , in which R A 9 is hydrogen, (C 1 -C 8 ) -alkyl, (C 1 -C 8 ) -haloalkyl, (C 1 -C 4 ) -alkoxy- (C 1 -C 4 ) -alkyl, (C 1 -C 6 ) -hydroxyalkyl, (C 3 - Ci 2) cycloalkyl or tri- (dC 4) -alkyl-silyl;
  • R A 6, R A 7, RA 8 are identical or different hydrogen, (Ci-C 8) alkyl, (CrC 8) -Halo- alkyl, (C3-Ci2) -cycloalkyl or substituted or unsubstituted phenyl; preferably:
  • dichlorophenylpyrazolecarboxylic acid derivatives S1 b
  • dichlorophenylpyrazolecarboxylic acid derivatives S1 b
  • compounds such as 1 - (2,4-dichlorophenyl) -5-methyl-pyrazol-3-carbonklareethyl- ester (S1 -2), 1 - (2,4-dichlorophenyl) - Ethyl 5-isopropyl-pyrazole-3-carboxylate (S1-3), 1- (2,4-dichlorophenyl) -5- (1,1-dimethyl-ethyl) -pyrazole-3-carboxylic acid ethyl ester (S1- 4) and related compounds, as in
  • EP-A-333,131 and EP-A-269,806 are described;
  • R B 1 is halogen, ( C 1 -C 4 ) -alkyl, ( C 1 -C 4 ) -alkoxy, nitro or (C 1 -C 4 ) -haloalkyl;
  • n B is a natural number from 0 to 5, preferably 0 to 3;
  • R B 2 is OR B 3 , SR b 3 or NR B 3 R B 4 or a saturated one
  • Hydrocarbon radical preferably having a total of 1 to 18 carbon atoms
  • RB 4 is hydrogen, (C 1 -C 6) alkyl, (C 1 -C 6) alkoxy or substituted or
  • T B is a (C 1 or C 2 ) alkanediyl chain which is unsubstituted or substituted by one or two (C 1 -C 4 ) -alkyl radicals or by [(C 1 -C 3) -alkoxy] -carbonyl; preferably:
  • Rc 1 is (Ci-C 4) alkyl, (Ci-C 4) -haloalkyl, (C 2 -C 4) alkenyl, (C 2 -C 4) haloalkenyl,
  • Rc 2, rc 3 are identical or different hydrogen, (Ci-C 4) -alkyl, (C2-C4) -alkenyl, (C 2 -C 4) alkynyl, (Ci-C 4) -haloalkyl, (C 2 -C 4) haloalkenyl, (dC 4) - Al kylcarbamoyl- (Ci -C 4) -alkyl, (C 2 -C 4) -alkyl kenylcarbamoyl- (Ci -C 4) -alkyl, (Ci - C 4 ) - alkoxy- (C 1 -C 4 ) -alkyl, dioxolanyl- (C 1 -C 4 ) -alkyl, thiazolyl, furyl, furylalkyl,
  • heterocyclic ring preferably an oxazolidine, thiazolidine,
  • R-28725" (3-dichloroacetyl-2,2, -dimethyl-1,3-oxazolidine) from Stauffer (S3-3),
  • AD-67 or "MON 4660” (3-dichloroacetyl-1-oxa-3-aza-spiro [4,5] decane) Company Nitrokemia or Monsanto (S3-7),
  • TI-35 (1-dichloroacetyl-azepane) from TRI-Chemical RT (S3-8),
  • Diaclonone (dicyclonone) or "BAS145138” or “LAB145138” (S3-9) ((RS) -1-dichloroacetyl-3,3,8a-trimethylperhydropyrrolo [1,2-a] pyrimidin-6-one) from BASF .
  • X D is CH or N
  • R D 1 is CO-NR D 5 R D 6 or NHCO-RD 7 ;
  • RD 2 is halogen, (C 1 -C 4 ) -haloalkyl, (C 1 -C 4 ) -haloalkoxy, nitro, (C 1 -C 4 ) -alkyl,
  • R D 3 is hydrogen, (C 1 -C 4 ) -alkyl, (C 2 -C 4 ) -alkenyl or (C 2 -C 4 ) -alkynyl;
  • R D 4 is halogen, nitro, (dC 4) -alkyl, (dC 4) -haloalkyl, (dC 4) haloalkoxy,
  • R D 5 is hydrogen, (C 1 -C 6 ) -alkyl, (C 3 -C 6 ) -cycloalkyl, (C 2 -C 6 ) -alkenyl, (C 2 -C 6 ) -alkynyl, (C 5 -C 6 ) ) -Cycloalkenyl, phenyl or 3- to 6-membered heterocyclyl containing v D heteroatoms from the group consisting of nitrogen, oxygen and
  • R D 6 is hydrogen, (C 1 -C 6 ) -alkyl, (C 2 -C 6 ) -alkenyl or (C 2 -C 6 ) -alkynyl, where the three last-mentioned radicals are represented by v D radicals from the group consisting of halogen, hydroxy , (C 1 -C 4 ) -alkyl, (C 1 -C 4 ) -alkoxy and (C 1 -C 4 ) -alkylthio, or
  • R D 7 is hydrogen, (C 1 -C 4 ) -alkylamino, di- (C 1 -C 4 ) -alkylamino, (C 1 -C 6 ) -alkyl,
  • Haloalkyl are substituted
  • n D 0, 1 or 2;
  • n D is 1 or 2;
  • v D is 0, 1, 2 or 3; preferred are compounds of the type of N-acylsulfonamides, for example the following formula (S4 a ), the z. B. are known from WO-A-97/45016 wherein
  • R D 4 is halogen, (C 1 -C 4 ) -alkyl, (C 1 -C 4 ) -alkoxy, CF 3;
  • v D is 0, 1, 2 or 3;
  • Acylsulfamoylbenzoeklareamide for example, the following formula (S4 b ), for example, are known from WO-A-99/16744,
  • RD 8 and RD 9 independently of one another are hydrogen, (C 1 -C 5 -alkyl, (C 3 -C 8) -cycloalkyl,
  • R D 4 is halogen, (C 1 -C 4 ) -alkyl, (C 1 -C 4 ) -alkoxy, CF 3
  • n D 1 or 2; for example
  • RE 1 , RE 2 are independently halogen, (C 1 -C 4 ) -alkyl, (C 1 -C 4 ) -alkoxy,
  • a E is COORE 3 or COSR E 4
  • RE 3 RE 4 are independently hydrogen, (dC 4) -alkyl, (C2-C6) - alkenyl, (C 2 -C 4) alkynyl, cyanoalkyl, (dC 4) -haloalkyl, phenyl,
  • n E is 0 or 1
  • n E 2 , n E 3 are each independently 0, 1 or 2, preferably:
  • Methyl diphenylmethoxyacetate (CAS No. 41858-19-9) (S7-1).
  • R F 1 is halogen, (dC 4) -alkyl, (dC 4) -haloalkyl, (dC 4) alkoxy, (dC 4) -haloalkoxy, nitro, (dC 4) alkylthio, (CrC 4) alkylsulfonyl, ( dC 4 ) alkoxycarbonyl, optionally substituted. Phenyl, optionally substituted phenoxy,
  • R F 2 is hydrogen or (C 1 -C 4 ) -alkyl
  • R F 3 is hydrogen, (C 1 -C 8 ) -alkyl, (C 2 -C 4 ) -alkenyl, (C 2 -C 4 ) -alkynyl, or aryl, where each of the abovementioned C-containing radicals is unsubstituted or is replaced by one or more a plurality, preferably up to three, identical or different radicals from the group consisting of halogen and alkoxy, or their salts, preferably compounds, in which
  • n F is an integer from 0 to 2
  • R F 1 is halogen, (dC 4) -alkyl, (dC 4) -haloalkyl, (dC 4) alkoxy, (dC 4) haloalkoxy,
  • R 2 is hydrogen or F (dC 4) -alkyl
  • R F 3 is hydrogen, (C 1 -C 8 ) -alkyl, (C 2 -C 4 ) -alkenyl, (C 2 -C 4 ) -alkynyl, or aryl, where each of the abovementioned C-containing radicals is unsubstituted or is replaced by one or more a plurality, preferably up to three, identical or different radicals from the group consisting of halogen and alkoxy is substituted, or their salts.
  • R G 1 is halogen, (C 1 -C 4 ) -alkyl, methoxy, nitro, cyano, CF 3 , OCF 3
  • n G is an integer from 0 to 4,
  • R G 2 is (C 1 -C 6 ) -alkyl, (C 2 -C 6 ) -alkenyl, (C 3 -C 6 ) -cycloalkyl, aryl; benzyl,
  • R G 3 is hydrogen or (Ci-C 6 ) -alkyl.
  • S1 1 active ingredients of the type of oxyimino compounds (S1 1), which are known as seed dressing, such.
  • Oxabetrinil ((Z) -1, 3-dioxolan-2-ylmethoxyimino (phenyl) acetonitrile) (S1 1 -1), which is known as a seedling safener for millet against damage from metolachlor,
  • Cyometrinil or “CGA-43089” ((Z) -cyanomethoxyimino (phenyl) acetonitrile) (S1 1 -3), which is known as a seed dressing safener for millet against damage by metolachlor.
  • Isothiochromanone (S12) class agents e.g. Methyl - [(3-oxo-1H-2-benzothiopyran-4 (3H) -ylidene) methoxy] acetate (CAS Reg.
  • Naphthalene anhydride (1,8-naphthalenedicarboxylic anhydride) (S13-1), which is known as
  • Seed pickling safener for maize known for damage from thiocarbamate herbicides
  • MG 191 (CAS Reg. No. 96420-72-3) (2-dichloromethyl-2-methyl-1,3-dioxolane) (S13-5) from Nitrokemia, which is known as safener for corn,
  • COD (1-Bromo-4- (chloromethylsulfonyl) benzene) from Kumiai, (CAS Registry No. 54091-06-4), which is known as a safener against damage of some herbicides in rice. S15) active substances, which are primarily used as herbicides, but also
  • 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, for example by pouring, spraying; Spraying, sprinkling.
  • the active compounds can also be used for controlling harmful plants in crops of known or yet to be developed genetically modified plants.
  • the transgenic plants are usually characterized by particular advantageous properties, for example by resistance to certain pesticides, especially certain herbicides, resistance to plant diseases or pathogens of plant diseases such as certain insects or microorganisms such as fungi, bacteria or viruses.
  • z. B the crop in terms of quantity, quality, shelf life, composition and special ingredients.
  • transgenic plants with increased starch content or altered quality of the starch or those with other fatty acid composition of the crop are known.
  • Crop plants are used, which are resistant to the phytotoxic effects of herbicides or have been made genetically resistant. Conventional ways of producing new plants that have modified properties compared to previously occurring plants exist
  • Glufosinate see, for example, EP-A-0242236, EP-A-242246) or glyphosate
  • transgenic crops characterized by a combination z.
  • B the above-mentioned new properties ("gene stacking") Numerous molecular biology techniques that can be used to produce novel transgenic plants with altered properties are known in principle; see, for. BI Potrykus and G. Spangenberg (eds.) Gene Transfer to Plants, Springer Lab Manual (1995), Springer Verlag Berlin, Heidelberg, or Christou, "Trends in Plant Science” 1 (1996) 423-431).
  • nucleic acid molecules can be introduced into plasmids that allow mutagenesis or sequence alteration by recombination of DNA sequences.
  • Standard methods can z. For example, base substitutions are made, partial sequences are removed, or natural or synthetic sequences are added.
  • adapters or linkers can be attached to the fragments, see, for example, US Pat. Sambrook et al., 1989, Molecular Cloning, A Laboratory Manual, 2nd Edition Cold Spring Harbor Laboratory Press, Cold Spring Harbor, NY; or Winnacker "Genes and Clones", VCH Weinheim 2nd edition 1996
  • Gene product can be obtained, for example, by the expression of at least one corresponding antisense RNA, a sense RNA to obtain a
  • DNA molecules may be used which comprise the entire coding sequence of a gene product, including any flanking sequences that may be present, as well as DNA molecules which comprise only parts of the coding sequence, which parts must be long enough to be present in the cells to cause an antisense effect. Also possible is the use of DNA sequences that encode a high degree of homology to those
  • the synthesized protein may be located in any compartment of the plant cell. But to achieve the localization in a particular compartment, z.
  • the coding region can be linked to DNA sequences that ensure localization in a particular compartment.
  • sequences are known to those of skill in the art (see, for example, Braun et al., EMBO J. 11 (1992), 3219-3227; Wolter et al., Proc. Natl. Acad., U.S.A. 85 (1988), 846-850; Sonnewald et al., Plant J. 1 (1991), 95-106).
  • the expression of the nucleic acid molecules can also take place in the organelles of the plant cells.
  • the transgenic plant cells can be regenerated to whole plants by known techniques.
  • the transgenic plants may, in principle, be plants of any plant species, that is, both monocotyledonous and dicotyledonous plants.
  • transgenic plants are available, the altered properties by
  • the compounds (I) according to the invention can be used in transgenic cultures which are resistant to growth substances, such as. B. Dicamba or against herbicides, the essential plant enzymes, eg. Acetolactate synthases (ALS), EPSP synthases, glutamine synthases (GS) or hydroxyphenylpyruvate
  • the essential plant enzymes eg. Acetolactate synthases (ALS), EPSP synthases, glutamine synthases (GS) or hydroxyphenylpyruvate
  • HPPD Dioxygenases
  • Harmful plants often have effects that are specific for application in the particular transgenic culture, for example a modified or specific one extended weed spectrum that can be controlled, changed effort amounts that can be used for the application, preferably good compatibility with the herbicides to which the transgenic culture is resistant, and influencing the growth and yield of the transgenic
  • the invention therefore also relates to the use of
  • 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 10g and 10kg of active ingredient per hectare
  • Soil area preferably between 50 g and 5 kg per hectare.
  • the preparation and the use of the active compounds according to the invention are evident from the following examples.
  • reaction solution thus obtained is cooled to 10 ° C and treated with 0.57 ml (0.004 mol) of triethylamine in 3 ml of dimethylformamide. Subsequently, 1 .43 ml
  • the resulting suspension is stirred for a further 2 hours.
  • Triphenylphosphine in 50ml tetrahydrofuran submitted. 9.97 ml (0.051 mol) of diisopropyl azodicarboxylate are slowly added dropwise and the mixture is stirred in for 5 hours
  • the test compounds formulated in the form of wettable powders (WP) or as emulsion concentrates (EC) are then applied to the surface of the cover soil as an aqueous suspension with an application rate of 800 l / ha with the addition of 0.2% wetting agent.
  • WP wettable powders
  • EC emulsion concentrates
  • the compounds 2-1 and 3-1 show a very strong action against weeds with partially good compatibility with crops.
  • WP wettable powders
  • EC emulsion concentrates
  • test compounds are then sprayed onto the green parts of plants as an aqueous suspension with a water application rate of about 800 l / ha with the addition of 0.2% wetting agent. After about 3 weeks of service life of
  • the compounds 2-1, 2-1 show its Na + salt and 3-1 with some good compatibility with crop plants very strong action against weeds.

Abstract

L'invention concerne de nouvelles oxathiazinyl-(hétéro) arylsulfonylurées de formule (I), un procédé pour leur préparation ainsi que leur utilisation en tant que pesticides et régulateurs de croissance des plantes, J représentant J-1 à J-4, J-1 à J-4 ayant les significations suivantes : et la flèche représentant à chaque fois une liaison au motif sulfonyle de la formule (I), E représentant une liaison directe, un alkylène, l'oxygène, un alkylamino ou le soufre, et A représentant N ou CR11, les radicaux R1 à R11 ayant les significations indiquées dans la description.
PCT/EP2010/064493 2009-10-01 2010-09-29 Oxathiazinyl-(hétéro) arylsulfonylurées, procédé et produits intermédiaires pour leur préparation et leur utilisation en tant que pesticides et régulateurs de croissance des plantes WO2011039276A1 (fr)

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