EP0851860A1 - 4-thiocarbamyl-1-(3-pyrazolyl)-pyrazoles et leur utilisation comme herbicides - Google Patents

4-thiocarbamyl-1-(3-pyrazolyl)-pyrazoles et leur utilisation comme herbicides

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Publication number
EP0851860A1
EP0851860A1 EP96929302A EP96929302A EP0851860A1 EP 0851860 A1 EP0851860 A1 EP 0851860A1 EP 96929302 A EP96929302 A EP 96929302A EP 96929302 A EP96929302 A EP 96929302A EP 0851860 A1 EP0851860 A1 EP 0851860A1
Authority
EP
European Patent Office
Prior art keywords
cyano
optionally substituted
alkyl
halogen
optionally
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.)
Withdrawn
Application number
EP96929302A
Other languages
German (de)
English (en)
Inventor
Karl-Heinz Linker
Kurt Findeisen
Wilhelm Haas
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 CropScience AG
Original Assignee
Bayer AG
Bayer CropScience 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, Bayer CropScience AG filed Critical Bayer AG
Publication of EP0851860A1 publication Critical patent/EP0851860A1/fr
Withdrawn legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D231/44—Oxygen and nitrogen or sulfur and nitrogen atoms
    • C07D231/52—Oxygen atom in position 3 and nitrogen atom in position 5, or vice versa
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D231/38—Nitrogen atoms
    • 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
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D231/18—One oxygen or sulfur atom
    • C07D231/20—One oxygen atom attached in position 3 or 5

Definitions

  • the invention relates to new 4-thiocarbamoyl-l- (3-pyrazolyl) pyrazoles, a process for their preparation and their use as herbicides.
  • R 1 represents optionally substituted alkyl
  • R stands for an optionally substituted radical from the series .Alkyl, alkoxy or .Alkylthio, or together with R 1 for the grouping
  • R represents hydrogen or halogen
  • R 4 represents hydrogen or optionally substituted alkyl
  • R 5 for hydrogen, cyano, nitro, thiocarbamoyl or halogen, for optionally substituted alkyl, for optionally substituted aryl, for the grouping -OR 6 , the grouping -S (O) n -R 7 , the grouping -NR 8 R 9 or the grouping -NR 10 -CY-R ⁇ ,
  • R 6 stands for hydrogen or for optionally substituted alkyl, alkenyl or alkynyl,
  • R 7 represents an optionally substituted radical of the series .Alkyl, alkenyl or alkynyl,
  • R 8 represents hydrogen or an optionally substituted radical from the series alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, aryl or arylalkyl,
  • R 9 represents hydrogen or an optionally substituted radical from the series .Alkyl, alkoxy, .alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, .aryl or aralkyl or for the grouping -S (O) n -R 7 or together with R 8 for Alkanediyl stands,
  • R 10 represents hydrogen or an optionally substituted radical from the series alkyl, alkenyl or alkynyl,
  • R 1 represents hydrogen, optionally substituted alkyl or optionally substituted aryl
  • n the numbers 2 or 3
  • n the numbers 0, 1 or 2
  • X represents CH 2 , O, S, S (O) n , NH or NCH 3 , and
  • Y stands for O or S.
  • R 1 , R 2 , R 3 , R 4 and R 5 have the meanings given above,
  • the new 4-thiocarbamoyl-l- (3-pyrazolyl) pyrazoles of the general formula (I) are notable for their strong herbicidal activity.
  • saturated or unsaturated hydrocarbon chains such as. Alkyl, alkanediyl, alkenyl or alkynyl - are also in connection with
  • Heteroatoms such as in alkoxy or alkylthio - in each case straight-chain or branched.
  • Halogen generally represents fluorine, chlorine, bromine or iodine, preferably fluorine, chlorine or bromine, in particular fluorine or chlorine.
  • the invention preferably relates to compounds of the formula (I) in which
  • R 1 represents alkyl which has 1 to 6 carbon atoms and is optionally substituted by cyano, halogen or C r C 4 -alkoxy,
  • R 2 stands for a radical of the series .Alkyl, .alkoxy or alkylthio, each optionally substituted by cyano, halogen or C j -C 4 -alkoxy, each having 1 to 6 carbon atoms, or together with R 1 for the grouping
  • R 3 represents hydrogen or halogen
  • R 4 represents hydrogen or alkyl, having 1 to 6 carbon atoms, optionally substituted by cyano, halogen or C 1-4 alkoxy,
  • R 5 for hydrogen, cyano, nitro, thiocarbamoyl or halogen, for alkyl optionally substituted by cyano, halogen or C - C 4 alkoxy having 1 to 6 carbon atoms, for optionally substituted by cyano, nitro, halogen, C r C 4 -Alkyl, C r C 4 -haloalkyl, C r C 4 -alkoxy or C r C 4 - haloalkoxy substituted phenyl, for the -OR 6 group , the -S (O) n -R 7 group , the -NR 8 group R 9 or the grouping -NR 10 -CY-R ⁇ ,
  • R 6 represents hydrogen, optionally by cyano, halogen, C 4 -C 4 alkoxy,
  • R 7 is optionally substituted by cyano, halogen, C - C 4 -alkoxy, C - C 4 -alkylcarbonyl or C - C 4 -alkoxy-carbonyl-substituted alkyl having 1 to 6 carbon atoms, or for each optionally substituted by cyano, halogen or C - C 4 -alkoxycarbonyl .Alkenyl or alkynyl each having 2 to 6 carbon atoms,
  • R 8 represents hydrogen, optionally substituted by cyano, halogen, C - C 4 alkoxy, C - C 4 alkyl carbonyl or C - C 4 alkoxy carbonyl substituted alkyl with 1 to 6 carbon atoms, for each alkenyl or alkynyl, optionally substituted by cyano, halo or C - C 4 alkoxycarbonyl, each having 2 to 6 carbon atoms, for each optionally substituted by cyano,
  • Alkyl with 1 to 6 carbon atoms each optionally , Halo ⁇ gene by cyano or C - C gen 4 -jAlkoxycarbonyl substituted alkenyl or alkinyl each having 2 to 6 carbon atoms, represents optionally cyano-, Halo ⁇ or C - C 4 alkoxy atoms substituted jAlkoxy having 1 to 6 carbon , for the grouping -S (O) n -R 7 , for each cycloalkyl or cycloalkylalkyl which is optionally substituted by cyano, halogen or C - C 4 -alkyl, each having 3 to 6 carbon atoms in the cycloalkyl groups and optionally 1 to 4 Carbon atoms in the alkyl groups, or for phenyl optionally substituted by cyano, thiocarbamoyl, nitro, halogen, C r C 4 alkyl, C r C 4 haloalkyl, C r
  • R 10 for hydrogen, for optionally by cyano, halogen, C - C 4 alkoxy,
  • R 11 represents hydrogen, represents optionally cyano-, halogen or C -C 4 -alk- oxy-substituted alkyl having 1 to 6 carbon atoms, C - C 4 halo-alkyl, C - C 4 alkoxy or C - C 4 -haloalkoxy or phenyl which is optionally substituted by cyano, nitro, halogen, C - C 4 -alkyl, C - C 4 -haloalkyl, C - C 4 - alkoxy or C - C 4 -haloalkoxy,
  • n the numbers 2 or 3
  • n the numbers 0, 1 or 2
  • X represents CH 2 , O, S, S (O) n , NH or NCH 3 , and
  • Y stands for O or S.
  • the invention relates in particular to compounds of the formula (I) in which R 1 represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, each optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy,
  • R 2 for methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, each optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy,
  • R 3 represents hydrogen, fluorine, chlorine or bromine
  • R 4 is hydrogen or is in each case optionally by cyano, fluorine, chlorine,
  • R 5 for hydrogen, cyano, nitro, thiocarbamoyl, fluorine, chlorine or bromine, for methyl, ethyl, n- or i-propyl, n-, i-, s-, each optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy or t-butyl, for optionally by cyano, nitro, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl, methoxy, ethoxy, n- or i-Propoxy, difluoromethoxy or trifluoromethoxy substituted phenyl, for the group -OR 6 , the grouping -S (O) n -R 7 , the grouping -NR 8 R 9 or the grouping -NR 10 -CY-R ⁇ stands,
  • R 6 for hydrogen, for each methyl, ethyl, n- or i-propyl, n-, i-, s- or t substituted by cyano, fluorine, chlorine, methoxy, ethoxy, acetyl, propionyl, methoxycarbonyl or ethoxycarbonyl Butyl, or for propenyl, butenyl, which is in each case optionally substituted by cyano, fluorine, chlorine, bromine, methoxycarbonyl or ethoxycarbonyl,
  • R for each optionally by cyano, fluorine, chlorine, methoxy, ethoxy,
  • R 8 for hydrogen, for each methyl, ethyl, n- or i-propyl, n-, i-, s- or t- substituted by cyano, fluorine, chlorine, methoxy, ethoxy, acetyl, propionyl, methoxycarbonyl or ethoxycarbonyl.
  • R 9 for hydrogen, for each optionally by cyano, fluorine, chlorine,
  • R 10 for hydrogen, for methyl, ethyl, n- or i-propyl, n-, i-, s- or t, each optionally substituted by cyano, fluorine, chlorine, methoxy, ethoxy, acetyl, propionyl, methoxycarbonyl or ethoxycarbonyl - Butyl, or for each optionally by cyano, fluorine, chlorine, bromine, Methoxycarbonyl or ethoxycarbonyl substituted propenyl, butenyl, propynyl or butynyl,
  • R 11 is hydrogen, for methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl which is optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy, or for optionally by cyano, nitro , Fluorine, chlorine,
  • n the numbers 2 or 3
  • n the numbers 0, 1 or 2
  • X represents CH 2 , O, S, S (O) n , NH or NCH 3 , and
  • Y stands for O or S.
  • R has the following meaning, for example:
  • R .5 has the meaning listed above under Group 1:
  • R 5 has, for example, the meaning listed above under Group 1:
  • R 5 has, for example, the meaning listed above under Group 1: Group 5
  • R 5 has, for example, the meaning listed above under Group 1:
  • R 5 has, for example, the meaning listed above under Group 1:
  • R 5 has, for example, the meaning listed above under Group 1: Group 8
  • R, 5 has, for example, the meaning listed above under Group 1:
  • R .5 has the meaning listed above under Group 1:
  • R has, for example, the meaning listed above in Group 1: Group 11
  • R, 5 has, for example, the meaning listed above under Group 1:
  • R 5 has, for example, the meaning listed above under Group 1:
  • R 5 has, for example, the meaning listed above under Group 1: Group 14
  • R .5 has the meaning listed above under Group 1:
  • R has, for example, the meaning listed above in Group 1:
  • R has, for example, the meaning listed above in Group 1: Group 17
  • R 5 has, for example, the meaning listed above under Group 1:
  • R has, for example, the meaning listed above in Group 1:
  • R has, for example, the meaning listed above in Group 1: Group 20
  • R has, for example, the meaning listed above in Group 1:
  • R has, for example, the meaning listed above in Group 1:
  • R, 5 has, for example, the meaning listed above under Group 1:
  • R has, for example, the meaning listed above in Group 1:
  • R .5 has the meaning listed above under Group 1:
  • R has, for example, the meaning listed above in Group 1:
  • Formula (II) provides a general definition of the 4-cyano-1- (3-pyrazolyl) pyrazoles to be used as starting materials in the process according to the invention for the preparation of the compounds of the formula (I).
  • R 1 , R 2 , R 3 , R 4 and R preferably or in particular have those meanings which are preferred or particularly preferred for R in the description of the compounds of the formula (I) to be prepared according to the invention 1 , R 2 , R 3 , R 4 and R 5 was specified.
  • the starting materials of the formula (II) are known and / or can be prepared by processes which are known per se (cf. EP 542388, WO 9408999).
  • the process according to the invention for the preparation of the compounds of the formula (I) is optionally carried out in the presence of a diluent.
  • a diluent is generally suitable as diluents. These preferably include aliphatic, alicyclic and aromatic, optionally halogenated hydrocarbons, such as, for example
  • MTBE Methyl t-butyl ether
  • TAME t-pentyl ether
  • THF 1,4-dioxane
  • ethylene glycol dimethyl ether or diethyl ether diethyl en-glycol dimethyl ether or diethyl ether
  • Dialkyl ketones such as, for example, acetone, butanone (methyl ethyl ketone), methyl i-propyl ketone or methyl i-butyl ketone, nitriles, such as, for example, acetonitrile, propionitrile, butyronitrile or benzonitrile
  • Amides such as, for example, N, N-dimethylformamide (DMF), N, N-dimethyl-acetamide, N-methylformanilide, N-methylpyrrolidone or hexamethylphosphoric acid triamide
  • Esters such as, for example, methyl acetate, ethyl ester, n- or i-propyl ester, n-, i- or s-butyl
  • the process according to the invention for the preparation of the compounds of the formula (I) is preferably carried out in the presence of a suitable reaction auxiliary.
  • the usual inorganic or organic bases or acid acceptors are generally suitable as reaction auxiliaries. These preferably include alkali metal or alkaline earth metal acetates, amides, carbonates, bicarbonates, hydrides, hydroxides or alkanolates, such as, for example, sodium, potassium or calcium acetate, lithium, sodium, potassium - or calcium amide, sodium, potassium or calcium carbonate, sodium, potassium or calcium hydrogen carbonate, lithium, sodium, potassium or calcium hydride, lithium, sodium, potassium or calcium hydroxide, sodium or potassium methoxide, ethanolate, n- or i-propanolate, n-, i-, s- or t-butanolate; basic organic nitrogen compounds, such as trimethylamine, triethylamine, tripropylamine, tributylamine, ethyldiisopropy
  • DBU diazabicyclo [5,4,0] - undec-7-ene
  • reaction temperatures can be varied within a substantial range when carrying out the process according to the invention. In general, temperatures between 0 ° C and 120 ° C, preferably between 10 ° C and 100 ° C.
  • the process according to the invention is generally carried out under normal pressure. However, it is also possible to carry out the process according to the invention under elevated or reduced pressure - generally between 0.1 bar and 10 bar.
  • the starting materials of the formula (II) are generally in a suitable diluent in counter were presented with a reaction aid and the hydrogen sulfide or thioacetic acid or thioacetamide is slowly metered in.
  • the reaction mixture is stirred at the required temperature until the end of the reaction.
  • Working up in the process according to the invention is carried out in each case by customary methods (cf. the preparation examples).
  • 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 one used
  • the active compounds according to the invention can e.g. can be used in the following plants:
  • Pisum Solanum, Linum, Ipomoea, Vicia, Nicotiana, Lycopersicon, Arachis, Brassica, Lactuca, Cucumis, Cucurbita.
  • Scirpus Paspalum, Ischaemum, Sphenoclea, Dactyloctenium, Agrostis, Alopecurus, Apera.
  • the compounds are suitable for total weed control, e.g. on industrial and track systems and on paths and
  • the compounds for weed control in permanent crops e.g. Forest, ornamental wood, fruit, wine, citrus, nut, banana, coffee, tea, rubber, oil palm, cocoa, berry fruit and hop plants, on ornamental and sports turf and pasture land and for selective purposes Weed control can be used in annual crops.
  • the compounds of formula (I) according to the invention are particularly suitable for the selective control of monocotyledon and dicotyledon weeds in monocotyledonous and dicotyledon crops both in the pre-emergence and in the post-emergence process.
  • the compounds of formula (I) also show insecticidal activity.
  • the active ingredients 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-impregnated natural and synthetic substances and very fine encapsulations in polymers Fabrics.
  • formulations are prepared in a known manner, e.g. B. by mixing the active ingredients with extenders, that is to say liquid solvents and / or solid carriers, if appropriate using surface-active agents, ie emulsifiers and / or dispersants and / or foam-generating agents.
  • extenders that is to say liquid solvents and / or solid carriers, if appropriate using surface-active agents, ie emulsifiers and / or dispersants and / or foam-generating agents.
  • organic solvents can, for example, also be used as auxiliary solvents.
  • auxiliary solvents include aromatics, such as xylene, toluene, or alkylnaphthalenes, chlorinated aromatics and chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chloroethylene or methylene chloride, aliphatic carbon Hydrogens, such as cyclohexane or paraffins, for example petroleum fractions, mineral and vegetable oils, alcohols, such as butanol or glycol, and their ethers and esters, ketones, such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents, such as dimethylformamide and dimethyl sulfoxide, as well as water.
  • aromatics such as xylene, toluene, or alkylnaphthalenes
  • chlorinated aromatics and chlorinated aliphatic hydrocarbons such
  • Solid carrier materials are suitable: e.g. Ammonium salts and natural rock powders such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and synthetic rock powders such as highly disperse silica, aluminum oxide and silicates are suitable as solid carriers for granules: e.g. broken and fractionated natural rocks like
  • nonionic and anionic emulsifiers such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, e.g. Alkylaryl polyglycol ethers, alkyl sulfonates
  • Adhesives such as carboxy methyl cellulose, 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 weed control in a mixture with known herbicides, finished formulations or tank mixes being possible.
  • known herbicides are suitable for the mixtures, for example anilides, such as, for example, diflufenican and propanil; .Arylcarboxylic acids, such as dichloropicolinic acid, dicamba and picloram; Aryl oxy alkanoic acids, such as, for example, 2.4 D, 2.4 DB, 2.4 DP, fluroxypyr, MCPA, MCPP and triclopyr; jAryloxy-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 chlorpropham, desmedip
  • Fomesafen, halosafen, lactofen and oxyfluorfen Ureas, e.g. Chlorotoluron, diuron, fluometuron, isoproturon, linuron and methabenzthiazuron; Hydroxylamines, e.g. .Alloxydim, clethodim, cycloxydim, sethoxydim and tralkoxydim; Imidazolinones, e.g. Imazethapyr, imazamethabenz, imazapyr and imazaquin; Nitriles, e.g. Bromoxynil, dichlobenil and ioxynil; Oxyacetamides, e.g.
  • Sulfonylureas e.g. Amidosulfuron, ben-sulfuron-methyl, chlorimuron-ethyl, chlorosulfuron, cinosulfuron, metsulfuron-methyl, nicosulfuron, primisulfuron, pyrazosulfuron-ethyl, thifensulfuron-methyl, triasulfuron and tribenuron-methyl;
  • Thiol carbamates e.g. Butylates, cycloates, dialallates, EPTC, esprocarb, molinates, prosulfocarb, thiobencarb and triallates;
  • Triazines e.g. Atrazin, cyanazin, simazin, simetryne, terbutryne and terbutylazine
  • Triazinones e.g. Hexazinone, metamitron and metribuzin
  • Others such as Aminotriazole, Benfuresate, Bentazone, Cinmethylin, Clomazone, Clopyralid, Difenzoquat, Dithiopyr, Ethofumesate, Fluorochloridone, Glufosinate, Glyphosate, Isoxaben, Pyridate, Quinchlorac, Quinmerac, Sulphosate and
  • 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 customary manner, for example by watering, spraying, spraying or scattering.
  • the active compounds according to the invention can be applied both before and after emergence of the plants. They can also be worked into the soil before sowing.
  • the amount of active ingredient used can vary over a wide range. It essentially depends on the type of effect desired. In general, the application rates are between 1 g and 10 kg of active ingredient per hectare of soil, preferably between 5 g and 5 kg per ha.
  • Solvent 5 parts by weight of acetone 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.
  • Seeds of the test plants are sown in normal soil. After about 24 hours, the active ingredient preparation is poured onto the floor.
  • the amount of water per unit area is expediently kept constant.
  • the concentration of active substance in the preparation is irrelevant; the decisive factor is only the amount of active substance applied per unit area.
  • the compound according to Preparation Example 1 shows very good activity against weeds such as Digitaria (80%), Echinochloa with good tolerance to crop plants, such as barley and cotton (0-10%) and an application rate of 125 g / ha (95%), Abutilon (100%), Amaranthus (100%) and Chenopodium (100%).
  • weeds such as Digitaria (80%), Echinochloa with good tolerance to crop plants, such as barley and cotton (0-10%) and an application rate of 125 g / ha (95%), Abutilon (100%), Amaranthus (100%) and Chenopodium (100%).
  • weeds such as Digitaria (80%), Echinochloa with good tolerance to crop plants, such as barley and cotton (0-10%) and an application rate of 125 g / ha (95%), Abutilon (100%), Amaranthus (100%) and Chenopodium (100%).
  • Example B shows very good activity against weeds such as Digitaria (80%), Echinochloa with good tolerance
  • 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 with a height of 5-15 cm are sprayed with the active substance preparation in such a way that the desired amounts of active substance are applied per unit area.
  • the concentration of the spray liquor is chosen so that the particular amounts of active compound desired are applied in 1000 l / ha.
  • the compound according to Preparation Example 1 shows good compatibility with crop plants, such as Wheat (10%) and an application rate of 250 g / ha very strong action against weeds such as

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

Abstract

L'invention concerne de nouveaux 4-thiocarbamyl-1-(3-pyrazolyl)-pyrazoles de la formule générale (I), dans laquelle R<1>, R<2>, R<3>, R<4> et R<5> ont les significations données dans la description. L'invention concerne par ailleurs un procédé permettant de les préparer et leur utilisation comme herbicides.
EP96929302A 1995-09-04 1996-08-22 4-thiocarbamyl-1-(3-pyrazolyl)-pyrazoles et leur utilisation comme herbicides Withdrawn EP0851860A1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE19532347A DE19532347A1 (de) 1995-09-04 1995-09-04 4-Thiocarbamoyl-1-(3-pyrazolyl)-pyrazole
DE19532347 1995-09-04
PCT/EP1996/003692 WO1997009313A1 (fr) 1995-09-04 1996-08-22 4-thiocarbamyl-1-(3-pyrazolyl)-pyrazoles et leur utilisation comme herbicides

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EP0851860A1 true EP0851860A1 (fr) 1998-07-08

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EP96929302A Withdrawn EP0851860A1 (fr) 1995-09-04 1996-08-22 4-thiocarbamyl-1-(3-pyrazolyl)-pyrazoles et leur utilisation comme herbicides

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US (1) US6025498A (fr)
EP (1) EP0851860A1 (fr)
JP (1) JPH11514346A (fr)
KR (1) KR19990044254A (fr)
CN (1) CN1070855C (fr)
AU (1) AU702537B2 (fr)
BR (1) BR9610193A (fr)
CA (1) CA2230788A1 (fr)
DE (1) DE19532347A1 (fr)
HK (1) HK1016163A1 (fr)
WO (1) WO1997009313A1 (fr)

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE19623892A1 (de) * 1996-06-06 1997-12-11 Hoechst Schering Agrevo Gmbh Substituierte Pyrazolyl-pyrazolderivate
DE19630555A1 (de) * 1996-07-18 1998-01-22 Hoechst Schering Agrevo Gmbh Substituierte Pyrazolyl-pyrazolderivate
DE19631865A1 (de) * 1996-08-08 1998-02-12 Bayer Ag Substituierte 1-(3-Pyrazolyl) -pyrazole
DE19751943A1 (de) * 1997-11-24 1999-05-27 Hoechst Schering Agrevo Gmbh 1-Methyl-5-alkylsulfonyl-, 1-Methyl-5-alkylsulfinyl- und 1-Methyl-5-alkylthio-substituierte Pyrazolylpyrazole, Verfahren zu ihrer Herstellung und ihre Verwendung als Herbizide
KR101551984B1 (ko) 2006-10-04 2015-09-09 제넨테크, 인크. Ｖｅｇｆ용 ｅｌｉｓａ
WO2019233372A1 (fr) * 2018-06-04 2019-12-12 海利尔药业集团股份有限公司 Composé de pyrazolyl pyrazole de sulfonamide substitué ou sel à activité pesticide acceptable de celui-ci et utilisation associée

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Publication number Priority date Publication date Assignee Title
IL103678A (en) * 1991-11-13 1996-09-12 Schering Ag History of pyrazolylpyrazole, processes for their preparation and herbicidal preparations containing them
DK0663913T3 (da) * 1992-10-12 1999-05-03 Hoechst Schering Agrevo Gmbh Nye substituerede pyrazolderivater, fremgangsmåder til deres fremstilling samt deres anvendelse som herbicider

Non-Patent Citations (1)

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Title
See references of WO9709313A1 *

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AU702537B2 (en) 1999-02-25
HK1016163A1 (en) 1999-10-29
CN1195339A (zh) 1998-10-07
BR9610193A (pt) 1998-12-15
DE19532347A1 (de) 1997-03-06
KR19990044254A (ko) 1999-06-25
CA2230788A1 (fr) 1997-03-13
AU6876196A (en) 1997-03-27
WO1997009313A1 (fr) 1997-03-13
US6025498A (en) 2000-02-15
JPH11514346A (ja) 1999-12-07
CN1070855C (zh) 2001-09-12

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