US20050009705A1 - Selective herbicides based on substituted thien-3-yl-sulfonylamino(thio)carbonyltriazolin(thi)ones and safeners - Google Patents

Selective herbicides based on substituted thien-3-yl-sulfonylamino(thio)carbonyltriazolin(thi)ones and safeners Download PDF

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US20050009705A1
US20050009705A1 US10/489,092 US48909204A US2005009705A1 US 20050009705 A1 US20050009705 A1 US 20050009705A1 US 48909204 A US48909204 A US 48909204A US 2005009705 A1 US2005009705 A1 US 2005009705A1
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substituted
chlorine
ethyl
cyano
methyl
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US10/489,092
Inventor
Dieter Feucht
Peter Dahmen
Mark Drewes
Rolf Pontzen
Ernst Gesing
Hans-Georg Schwarz
Klaus-Helmut Muller
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Bayer CropScience AG
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Bayer CropScience AG
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Assigned to BAYER CROPSCIENCE AG reassignment BAYER CROPSCIENCE AG ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: DREWES, MARK WILHELM, FEUCHT, DIETER, DAHMEN, PETER, PONTZEN, ROLF, SCHWARTZ, HANS-GEORG, GESING, ERNST RUDOLF F., MULLER, KLAUS-HELMUT
Publication of US20050009705A1 publication Critical patent/US20050009705A1/en
Priority to US13/873,656 priority Critical patent/US9968091B2/en
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Assigned to BAYER INTELLECTUAL PROPERTY GMBH reassignment BAYER INTELLECTUAL PROPERTY GMBH CORRECTIVE ASSIGNMENT TO CORRECT THE ASSIGNEE ADDRESS PREVIOUSLY RECORDED AT REEL: 034892 FRAME: 0286. ASSIGNOR(S) HEREBY CONFIRMS THE ASSIGNMENT. Assignors: BAYER CROPSCIENCE AG
Priority to US14/950,588 priority patent/US10524475B2/en
Assigned to BAYER CROPSCIENCE AKTIENGESELLSCHAFT reassignment BAYER CROPSCIENCE AKTIENGESELLSCHAFT ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: BAYER INTELLECTUAL PROPERTY GMBH
Priority to US16/690,200 priority patent/US20200085058A1/en
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    • 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<
    • A01N47/38—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the group >N—CO—N< where at least one nitrogen atom is part of a heterocyclic ring; Thio analogues thereof
    • 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
    • A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
    • A01N25/32—Ingredients for reducing the noxious effect of the active substances to organisms other than pests, e.g. toxicity reducing compositions, self-destructing compositions
    • 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
    • A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
    • A01N43/647—Triazoles; Hydrogenated triazoles
    • A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles

Definitions

  • the invention relates to novel selective herbicidal active compound combinations which comprise substituted thien-3-ylsulphonylamino(thio)carbonyltriazolin(ethi)ones and at least one compound which improves crop plant compatibility and which can be used with particularly good results for the selective control of weeds in various crops of useful plants.
  • the invention provides selective herbicidal compositions, characterized by an effective amount of an active compound combination comprising
  • hydrocarbon chains such as in alkyl or alkanediyl
  • the hydrocarbon chains are in each case straight-chain or branched—including in combination with hetero atoms, such as in alkoxy.
  • R 1 and R 2 represent methyl, ethyl, n- or i-propyl.
  • Preferred active compound components of group 1 are in particular also the sodium, potassium, magnesium, calcium, ammonium, C 1 -C 4 -alkylammonium-, di-(C 1 -C 4 -alkyl)ammonium-, tri-(C 1 -C 4 -alkyl)ammonium, tetra-(C 1 -C 4 -alkyl)ammonium, tri-(C 1 -C 4 -alkyl)sulphonium-, C 5 - or C 6 -cycloalkylammonium and di-(C 1 -C 2 -alkyl)-benzylammonium salts of compounds of the formula (I) in which Q 1 , Q 2 , R 1 , R 2 , R 3 and R 4 have the meanings given above as being preferred.
  • herbicide safeners of the formulae (Ia), (IIb), (IIc), (IId) and (IIe) are defined below.
  • Table 2 Examples of the compounds of the formula (IIa) (IIa) Example No. (positions) (X 1 ) n A 1 R 5 IIa-1 (2) Cl, (4) Cl OCH 3 IIa-2 (2) Cl, (4) Cl OCH 3 IIa-3 (2) Cl, (4) Cl OC 2 H 5 IIa-4 (2) Cl, (4) Cl OC 2 H 5 IIa-5 (2) Cl OCH 3 IIa-6 (2) Cl, (4) Cl OCH 3 IIa-7 (2) F OCH 3 IIa-8 (2) F OCH 3 IIa-9 (2) Cl, (4) Cl OC 2 H 5 IIa-10 (2) Cl, (4) CF 3 OCH 3 IIa-11 (2) Cl OCH 3 IIa-12 — OC 2 H 5 IIa-13 (2) Cl, (4) Cl OC 2 H 5 IIa-14 (2) Cl, (4) Cl OC 2 H 5 IIa-15 (2) Cl, (4) Cl OC 2 H 5 IIa-16 (2) Cl, (4) Cl OC 2 H 5 IIa-17 (2) Cl, (4) Cl OC 2 H 5 H 5
  • the compounds of the general formula (IIa) to be used as safeners according to the invention are known and/or can be prepared by processes known per se (cf. WO-A-91/07874, WO-A-95/07897).
  • the compounds of the general formula (IIb) to be used as safeners according to the invention are known and/or can be prepared by processes known per se (cf. EP-A-191736).
  • the compounds of the general formula (IIc) to be used as safeners according to the invention are known and/or can be prepared by processes known per se (cf. DE-A-22180974, DE-A-2350547).
  • the compounds of the general formula (IId) to be used as safeners according to the invention are known and/or can be prepared by processes known per se (cf. DE-A-19621522/U.S. Pat. No. 6,235,680/WO 97/45016).
  • the compounds of the general formula (IIe) to be used as safeners according to the invention are known and/or can be prepared by processes known per se (cf. WO-A-99/66795/U.S. Pat. No. 6,251,827).
  • the active compound combinations according to the invention can be used, for example, in connection with the following plants:
  • crop plants are all plants and plant varieties including transgenic plants and plant varieties, where on transgenic plants and plant varieties it is also possible for synergistic effects to occur.
  • the advantageous effect of the crop plant compatibility of the active compound combinations according to the invention is particularly highly pronounced at certain concentration ratios.
  • the weight ratios of the active compounds in the active compound concentrations can be varied within relatively wide ranges. In general, 0.001 to 1000 parts by weight, preferably 0.01 to 100 parts by weight, and particularly preferably 0.1 to 50 parts by weight and most preferably 1 to 25 parts by weight of one of the compounds which improve crop plant compatibility mentioned under group 2 above (antidotes/safeners) are present per part by weight of active compound of the formula (I) or its salts.
  • the active compounds or active compound combinations can be converted into the customary formulations, such as solutions, emulsions, wettable powders, suspensions, powders, dusting agents, pastes, soluble powders, granules, suspoemulsion concentrates, natural and synthetic materials impregnated with active compound, and very fine capsules in polymeric substances.
  • formulations are produced in a known manner, for example by mixing the active compounds with extenders, that is liquid solvents and/or solid carriers, optionally with the use of surfactants, that is emulsifiers and/or dispersants and/or foam-formers.
  • Suitable liquid solvents are essentially: aromatics, such as xylene. toluene or alkylnaphthalenes, chlorinated aromatics and chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chloroethylenes or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, for example petroleum fractions, mineral and vegetable oils, alcohols, such as butanol or glycol, and also their ethers and esters, ketones, such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents, such as dimethylformamide and dimethyl sulphoxide, and also water.
  • aromatics such as xylene. toluene or alkylnaphthalenes
  • chlorinated aromatics and chlorinated aliphatic hydrocarbons such as chlorobenzenes, chloroethylenes or methylene chlor
  • Suitable solid carriers are:
  • Tackifiers such as carboxymethylcellulose and natural and synthetic polymers in the form of powders, granules or latices, such as gum arabic, polyvinyl alcohol and polyvinyl acetate, and also natural phospholipids, such as cephalins and lecithins, and synthetic phospholipids, can be used in the formulations.
  • Other possible additives are mineral and vegetable oils.
  • colorants such as inorganic pigments, for example iron oxide, titanium oxide and Prussian Blue, and organic dyestuffs, such as alizarin dyestuffs, azo dyestuffs and metal phthalocyanine dyestuffs, and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.
  • organic dyestuffs such as alizarin dyestuffs, azo dyestuffs and metal phthalocyanine dyestuffs
  • trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.
  • the formulations generally comprise from 0.1 to 95 per cent by weight of active compounds including the safeners, preferably between 0.5 and 90%.
  • the active compound combinations according to the invention are generally used in the form of finished formulations.
  • the active compounds contained in the active compound combinations can also be mixed in individual formulations when used, i.e. in the form of tank mixes.
  • novel active compound combinations can furthermore be used as a mixture with other known herbicides, finished formulations or tank mixes again being possible.
  • a mixture with other known active compounds such as fungicides, insecticides, acaricides, nematicides, bird repellents, growth factors, plant nutrients and agents which improve soil structure, is also possible.
  • novel active compound combinations 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. They are used in the customary manner, for example by washing, spraying, atomizing, dusting or scattering.
  • the amounts of the active compound combinations according to the invention applied can be varied within a certain range; they depend, inter alia. on the weather and on soil factors. In general, the application rates are between 0.001 and 5 kg per ha, preferably between 0.001 and 1 kg per ha, particularly preferably between 0.003 and 0.5 kg per ha.
  • the active compound combinations according to the invention can be applied before and after emergence of the plants, that is to say by the pre-emergence and post-emergence method.
  • the active compound or safener components are in each case dissolved in a few ml (generally 2-3 ml) of solvent (generally acetone or N,N-dimethyl-formamide), and the solutions are combined and then—if appropriate after addition of an emulsifier—diluted with water to the desired concentration.
  • solvent generally acetone or N,N-dimethyl-formamide
  • an aqueous spray liquor was prepared using 0.1% of the additive Renex-36.
  • test plants are grown under controlled conditions (temperature, light, atmospheric humidity) in a greenhouse.
  • the test plants are sprayed when they have reached a height of 5-15 cm.
  • concentration of the spray liquor is chosen such that the particular amounts of active compound desired are applied in 500 l of water/ha.
  • the pots with the test plants are kept in a greenhouse chamber under controlled conditions (temperature, light, atmospheric humidity) until the test has ended. About three weeks after the application, the degree of damage to the crop plants is rated in % damage in comparison to the development of the untreated control.
  • an aqueous spray liquor comprising 0.5% of the additive Renex-36 was prepared.
  • Ex.-No. IId-25 TABLE A-2-1 Post-emergence test/greenhouse Damage winter Active compound Application rate barley (+ safener) (g of a.i./ha) (in %) I-2, sodium salt 4 60 2 50 I-2, sodium salt + 4 + 100 50 Comp. No. IId-25 2 + 100 25 4 + 30 50 2 + 30 35
  • the compound I-2 was used as 10 WP.
  • Marlipal® was added in an amount of 500 ml/ha.
  • Maize 3 maize of the cultivar “LIXIS” TABLE A-3-1 Post-emergence test/greenhouse Damage Application rate maize 1 Active compound (+ safener) (g of a.i./ha) (in %) I-2 15 20 8 10 I-2 + Comp. No. IId-25 15 + 100 5 8 + 100 0
  • Mefenpyr-diethyl was used as 100 EC.
  • Mefenpyr-diethyl was used as 100 EC and the compound of Ex. No. I-2 was used as 10 WP. TABLE A-5-1 Post-emergence test/greenhouse Application rate Damage winter Active compound (+ safener) (g of a.i./ha) wheat (in %) I-2 30 60 mefenpyr-diethyl 50 0 I-2 + mefenpyr-diethyl 30 + 50 5

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  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Dentistry (AREA)
  • Plant Pathology (AREA)
  • Engineering & Computer Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Agronomy & Crop Science (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Toxicology (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

The invention relates to selective herbicidal compositions that comprise an effective amount of an active compound combination comprising
(a) one or more compounds of the formula (I)
Figure US20050009705A1-20050113-C00001
in which Q1, Q2, R1, R2, R3 and R4 are as defined in the disclosure and salts of the compounds of the formula (I) and (b) at least one of the crop-plant-compatibility-improving compounds listed in the disclosure. The invention further relates to the use of these compositions for controlling undesirable vegetation and to a process for preparing the compositions according to the invention.

Description

  • The invention relates to novel selective herbicidal active compound combinations which comprise substituted thien-3-ylsulphonylamino(thio)carbonyltriazolin(ethi)ones and at least one compound which improves crop plant compatibility and which can be used with particularly good results for the selective control of weeds in various crops of useful plants.
  • Substituted thien-3-ylsulphonylamino(thio)carbonyltriazoline(ethi)ones are already known as effective herbicides (cf. WO-A-01/05788). However, the activity of these compounds and/or their compatibility with crop plants are not entirely satisfactory under all conditions.
  • Surprisingly, it has now been found that certain substituted thien-3-ylsulphonylamino-(thio)carbonyltriazolin(ethi)ones, when used together with the crop-plant-compatibility-improving compounds (safeners/antidotes) described below, prevent damage to crop plants extremely well and can be used particularly advantageously as broad-spectrum combination preparations for the selective control of weeds in crops of useful plants, such as, for example, in cereals and maize.
  • The invention provides selective herbicidal compositions, characterized by an effective amount of an active compound combination comprising
  • (a) substituted thien-3-ylsulphonylamino(thio)carbonyltriazolin(ethi)ones of the formula (I)
    Figure US20050009705A1-20050113-C00002
    in which
      • Q1 represents O (oxygen) or S (sulphur),
      • Q2 represents O (oxygen) or S (sulphur),
      • R1 represents optionally cyano-, halogen- or C1-C 4-alkoxy-substituted alkyl having 1 to 6 carbon atoms, represents in each case optionally cyano- or halogen-substituted alkenyl or alkynyl having in each case 2 to 6 carbon atoms, represents in each case optionally cyano-, halogen- or C1-C4-alkyl-substituted cycloalkyl or cycloalkylalkyl having in each case 3 to 6 carbon atoms in the cycloalkyl group and, if appropriate, 1 to 4 carbon atoms in the alkyl moiety, represents in each case optionally nitro-, cyano-, halogen-, C1-C4-alkyl- or C1-C4-alkoxy-substituted aryl or arylalkyl having in each case 6 or 10 carbon atoms in the aryl group and, if appropriate, 1 to 4 carbon atoms in the alkyl moiety, or represents in each case optionally nitro-, cyano-, halogen-, C1-C4-alkyl- or C1-C4-alkoxy-substituted heterocyclyl or heterocyclylalkyl having in each case up to 6 carbon atoms and additionally 1 to 4 nitrogen atoms and/or 1 or 2 oxygen or sulphur atoms in the heterocyclyl group and, if appropriate, 1 to 4 carbon atoms in the alkyl moiety,
      • R2 represents hydrogen, cyano, nitro, halogen, represents in each case optionally cyano-, halogen- or C1-C4-alkoxy-substituted alkyl, alkoxy, alkoxycarbonyl, alkylthio. alkylsulphinyl or alkylsulphonyl having in each case 1 to 6 carbon atoms in the alkyl group, or represents in each case optionally cyano- or halogen-substituted alkenyl, alkynyl, alkenyloxy or alkynyloxy having in each case 2 to 6 carbon atoms in the alkenyl or alkynyl group,
      • R3 represents hydrogen, hydroxyl, mercapto, amino, cyano, fluorine, chlorine, bromine, iodine, represents optionally fluorine-, chlorine-, bromine-, cyano-, C1-C4-alkoxy-, C1-C4-alkyl-carbonyl- or C1-C4-alkoxy-carbonyl-substituted alkyl having 1 to 6 carbon atoms, represents in each case optionally fluorine-, chlorine- and/or bromine-substituted alkenyl or alkynyl having in each case 2 to 6 carbon atoms, represents in each case optionally fluorine-, chlorine-, cyano-, C1-C4-alkoxy- or C1-C4-alkoxy-carbonyl-substituted alkoxy, alkylthio, alkylamino or alkylcarbonylamino having in each case 1 to 6 carbon atoms in the alkyl group, represents alkenyloxy, alkynyloxy, alkenylthio, alkynylthio, alkenylamino or alkynylamino having in each case 3 to 6 carbon atoms in the alkenyl or alkynyl group, represents dialkylamino having in each case 1 to 4 carbon atoms in the alkyl groups, represents in each case optionally methyl- and/or ethyl-substituted aziridino, pyrrolidino, piperidino and/or morpholino, represents in each case optionally fluorine-, chlorine-, bromine-, cyano- and/or C1-C4-alkyl-substituted cycloalkyl, cycloalkenyl, cycloalkyloxy, cycloalkylthio, cycloalkylamino, cycloalkylalkyl, cycloalkylalkoxy, cycloalkylalkylthio or cycloalkylalkylamino having in each case 3 to 6 carbon atoms in the cycloalkyl or cycloalkenyl group and, if appropriate, 1 to 4 carbon atoms in the alkyl moiety, or represents in each case optionally fluorine-, chlorine-, bromine-, cyano-, nitro-, C1-C4-alkyl-, trifluoromethyl-, C1-C4-alkoxy- and/or C1-C4-alkoxy-carbonyl-substituted aryl, arylalkyl, aryloxy, arylalkoxy, arylthio, arylalkylthio, arylamino or arylalkylamino having in each case 6 or 10 carbon atoms in the aryl group and, if appropriate, 1 to 4 carbon atoms in the alkyl moiety,
      • R4 represents hydrogen, hydroxyl, amino, cyano, represents C2-C10-alkylidene-amino, represents optionally fluorine-, chlorine-, bromine-, cyano-, C1-C4-alkoxy-, C1-C4-alkyl-carbonyl- or C1-C4-alkoxy-carbonyl-substituted alkyl having 1 to 6 carbon atoms, represents in each case optionally fluorine-, chlorine- and/or bromine-substituted alkenyl or alkynyl having in each case 2 to 6 carbon atoms, represents in each case optionally fluorine-, chlorine-, bromine-, cyano-, C1-C4-alkoxy- or C1-C4-alkoxy-carbonyl-substituted alkoxy, alkylamino or alkyl-carbonylamino having in each case 1 to 6 carbon atoms in the alkyl group, represents alkenyloxy having 3 to 6 carbon atoms, represents dialkylamino having in each case 1 to 4 carbon atoms in the alkyl groups, represents in each case optionally fluorine-, chlorine-, bromine-, cyano- and/or C1-C4-alkyl-substituted cycloalkyl, cycloalkylamino or cycloalkylalkyl having in each case 3 to 6 carbon atoms in the alkyl group and, if appropriate, 1 to 4 carbon atoms in the alkyl moiety, or represents in each case optionally fluorine-, chlorine-, bromine-, cyano- nitro-, C1-C4-alkyl-, trifluoromethyl- and/or C1-C4-alkoxy-substituted aryl or arylalkyl having in each case 6 or 10 carbon atoms in the aryl group and, if appropriate, 1 to 4 carbon atoms in the alkyl moiety, or
      • R3 and R4 together represent optionally branched alkanediyl having 3 to 6 carbon atoms,
      • and salts of the compounds of the formula (I)
      • (“active compounds of group 1”)
        and
  • (b) at least one compound which improves crop plant compatibility, from the group of compounds below:
      • 4-dichloroacetyl-1-oxa-4-aza-spiro[4.5]-decane (AD-67, MON-4660), 1-dichloro-acetyl-hexahydro-3,3,8a-trimethylpyrrolo[1,2-a]-pyrimidin-6(2H)-one (dicyclonon, BAS-145138), 4-dichloroacetyl-3,4-dihydro-3-methyl-2H-1,4-benzoxazine (benoxacor), 1-methyl-hexyl 5-chloro-quinolin-8-oxy-acetate (cloquintocet-mexyl—cf. also related compounds in EP-A-86750, EP-A-94349, EP-A-191736, EP-A-492366), 3-(2-chloro-benzyl)-1-(1-methyl-1-phenyl-ethyl)-urea (cumyluron), α-(cyanomethoximino)-phenylacetonitrile (cyometrinil), 2,4-dichloro-phenoxyacetic acid (2,4-D), 4-(2,4-dichloro-phenoxy)-butyric acid (2,4-DB), 1-(1-methyl-1-phenyl-ethyl)-3-(4-methyl-phenyl)-urea (daimuron, dymron), 3,6-dichloro-2-methoxy-benzoic acid (dicamba), S-1-methyl-1-phenyl-ethyl piperidine-1-thiocarboxylate (dimepiperate), 2,2-dichloro-N-(2-oxo-2-(2-propenylamino)-ethyl)-N-(2-propenyl)-acetamide (DKA-24), 2,2-dichloro-N,N-di-2-propenyl-acetamide (dichlormid), 4,6-dichloro-2-phenyl-pyrimidine (fenclorim), ethyl 1-(2,4-dichloro-phenyl)-5-trichloro-methyl-1H-1,2,4-triazole-3-carboxylate (fenchlorazole-ethyl—cf. also related compounds in EP-A-174562 and EP-A-346620), phenyl-methyl 2-chloro-4-trifluoromethyl-thiazole-5-carboxylate (flurazole), 4-chloro-N-(1,3-dioxolan-2-yl-methoxy)-α-trifluoro-acetophenone oxime (fluxofenim), 3-dichloroacetyl-5-(2-furanyl)-2,2-dimethyl-oxazolidine (furilazole, MON-13900), ethyl 4,5-dihydro-5,5-diphenyl-3-isoxazolecarboxylate (isoxadifen-ethyl—cf. also related compounds in WO-A-95/07897), 1-(ethoxycarbonyl)-ethyl-3,6-dichloro-2-methoxybenzoate (lactidichlor), (4-chloro-o-tolyloxy)-acetic acid (MCPA), 2-(4-chloro-o-tolyloxy)-propionic acid (mecoprop), diethyl 1-(2,4-dichloro-phenyl)-4,5-dihydro-5-methyl-1H-pyrazole-3,5-dicarboxylate (mefenpyr-diethyl—cf. also related compounds in WO-A-91/07874), 2-dichloromethyl-2-methyl-1,3-dioxolane (MG-191), 2-propenyl-1-oxa-4-azaspiro[4.5]decane 4-carbodithioate (MG-838), 1,8-naphthalic anhydride, α-(1,3-dioxolan-2-yl-methoximino)-phenylacetonitrile (oxabetrinil), 2,2-dichloro-N-(1,3-dioxolan-2-yl-methyl)-N-(2-propenyl)-acetamide (PPG-1292), 3-dichloroacetyl-2,2-dimethyl-oxazolidine (R-28725), 3-dichloroacetyl-2,2,5-trimethyl-oxazolidine (R-29148), 4-(4-chloro-o-tolyl)-butyric acid, 4-(4-chloro-phenoxy)-butyric acid, diphenylmethoxyacetic acid, methyl diphenylmethoxyacetate (MON-7400, cf. U.S. Pat. No. 4,964,893), ethyl diphenylmethoxyacetate, methyl 1-(2-chloro-phenyl)-5-phenyl-1H-pyrazole-3-carboxylate, ethyl 1-(2,4-dichloro-phenyl)-5-methyl-1H-pyrazole-3-carboxylate, ethyl 1-(2,4-dichloro-phenyl)-5-isopropyl-1H-pyrazole-3-carboxylate, ethyl 1-(2,4-dichloro-phenyl)-5-(1,1-dimethyl-ethyl)-1H-pyrazole-3-carboxylate, ethyl 1-(2,4-dichloro-phenyl)-5-phenyl-1H-pyrazole-3-carboxylate (cf. also related compounds in EP-A-269806 and EP-A-333131), ethyl 5-(2,4-dichloro-benzyl)-2-isoxazoline-3-carboxylate, ethyl 5-phenyl-2-isoxazoline-3-carboxylate, ethyl 5-(4-fluoro-phenyl)-5-phenyl-2-isoxazoline-3-carboxylate (cf. also related compounds in WO-A-91/08202), 1,3-dimethyl-but-1-yl 5-chloro-quinolin-8-oxy-acetate, 4-allyloxy-butyl 5-chloro-quinolin-8-oxy-acetate, 1-allyloxy-prop-2-yl 5-chloro-quinolin-8-oxy-acetate, methyl 5-chloro-quinolin-8-oxy-acetate, ethyl 5-chloro-quinolin-8-oxy-acetate, allyl 5-chloro-quinolin-8-oxy-acetate, 2-oxo-prop-1-yl 5-chloro-quinolin-8-oxy-acetate, diethyl 5-chloro-quinolin-8-oxy-malonate, diallyl 5-chloro-quinolin-8-oxy-malonate, diethyl 5-chloro-quinolin-8-oxy-malonate (cf. also related compounds in EP-A-582198), 4-carboxy-chroman-4-yl-acetic acid (AC-304415, cf. EP-A-613618), 4-chloro-phenoxyacetic acid, 3,3′-dimethyl-4-methoxy-benzophenone, 1-bromo-4-chloromethylsulphonyl-benzene, 1-[4-(N-2-methoxybenzoylsulphamoyl)-phenyl]-3-methyl-urea (alias N-(2-methoxy-benzoyl)-4-[(methylamino-carbonyl)-amino]-benzenesulphonamide), 1-[4-(N-2-methoxybenzoylsulphamoyl)-phenyl]-3,3-dimethyl-urea, 1-[4-(N-4,5-dimethylbenzoylsulphamoyl)-phenyl]-3-methyl-urea, 1-[4-(N-naphthylsulphamoyl)-phenyl]-3,3-dimethyl-urea, N-(2-methoxy-5-methyl-benzoyl)-4-(cyclopropyl-aminocarbonyl)-benzenesulphonamide,
        and/or the following compounds
        of the formula (IIa)
        Figure US20050009705A1-20050113-C00003
        or the formula (IIb)
        Figure US20050009705A1-20050113-C00004
        or the formula (IIc)
        Figure US20050009705A1-20050113-C00005
        where
      • n represents a number between 0 and 5,
      • A1 represents one of the divalent heterocyclic groupings shown below,
        Figure US20050009705A1-20050113-C00006
      • A2 represents optionally C1-C4-alkyl- and/or C1-C4-alkoxy-carbonyl-substituted alkanediyl having 1 or 2 carbon atoms,
      • R5 represents hydroxyl, mercapto, amino, C1-C6-alkoxy, C1-C6-alkylthio, C1-C6-alkylamino or di-(C1-C4-alkyl)-amino,
      • R6 represents hydroxyl, mercapto, amino, in each case optionally C1-C4-alkyl, C1-C4-alkoxy or C2-C4-alkenoxy-substituted C1-C6-alkoxy, C2-C6-alkenoxy, C1-C6-alkylthio, C1-C6-alkylamino or di-(C1-C4-alkyl)-amino,
      • R7 represents in each case optionally fluorine-, chlorine- and/or bromine-substituted C1-C4-alkyl,
      • R8 represents hydrogen, in each case optionally fluorine-, chlorine- and/or bromine-substituted C1-C6-alkyl, C2-C6-alkenyl or C2-C6-alkynyl, C1-C4-alkoxy-C1-C4-alkyl, dioxolanyl-C1-C4-alkyl, furyl, furyl-C1-C4-alkyl, thienyl, thiazolyl, piperidinyl, or optionally fluorine-, chlorine- and/or bromine- or C1-C4-alkyl-substituted phenyl,
      • R9 represents hydrogen, in each case optionally fluorine-, chlorine- and/or bromine-substituted C1-C6-alkyl, C2-C6-alkenyl or C2-C6-alkynyl, C1-C4-alkoxy-C1-C4-alkyl, dioxolanyl-C1-C4-alkyl, furyl, furyl-C1-C4-alkyl, thienyl, thiazolyl, piperidinyl, or optionally fluorine-, chlorine- and/or bromine- or C1-C4-alkyl-substituted phenyl, or together with R8 represents C3-C6-alkanediyl or C2-C5-oxaalkanediyl, each of which is optionally substituted by C1-C4-alkyl, phenyl, furyl, a fused-on benzene ring or by two substituents which together with the C atom to which they are attached form a 5- or 6-membered carbocycle,
      • R10 represents hydrogen, cyano, halogen, or represents in each case optionally fluorine, chlorine- and/or bromine-substituted C1-C4-alkyl, C3-C6-cycloalkyl or phenyl,
      • R11 represents hydrogen, optionally hydroxyl-, cyano-, halogen- or C1-C4-alkoxy-substituted C1-C6-alkyl, C3-C6-cycloalkyl or tri-(C1-C4-alkyl)-silyl,
      • R12 represents hydrogen, cyano, halogen, or represents in each case optionally fluorine-, chlorine- and/or bromine-substituted C1-C4-alkyl, C3-C6-cycloalkyl or phenyl,
      • X1 represents nitro, cyano, halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy or C1-C4-haloalkoxy,
      • X2 represents hydrogen, cyano, nitro, halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy or C1-C4-haloalkoxy,
      • X3 represents hydrogen, cyano, nitro, halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy or C1-C4-haloalkoxy,
        where X1 is preferably found at the (2) and (4) positions, X2 is preferably found at the (5) position and X3 is found at the (2) position,
        and/or the following compounds
        of the formula (IId)
        Figure US20050009705A1-20050113-C00007
        or the formula (IIe)
        Figure US20050009705A1-20050113-C00008
        where
      • n again represents a number between 0 and 5,
      • R13 represents hydrogen or C1-C4-alkyl,
      • R14 represents hydrogen or C1-C4-alkyl,
      • R15 represents hydrogen, in each case optionally cyano-, halogen- or C1-C4-alkoxy-substituted C1-C6-alkyl, C1-C6-alkoxy, C1-C6-alkylthio, C1-C6-alkylamino or di-(C1-C4-alkyl)-amino, or in each case optionally cyano-, halogen- or C1-C4-alkyl-substituted C3-C6-cycloalkyl, C3-C6-cycloalkyloxy, C3-C6-cycloalkylthio or C3-C6-cycloalkylamino,
      • R16 represents hydrogen, optionally cyano-, hydroxyl-, halogen- or C1-C4-alkoxy-substituted C1-C6-alkyl, in each case optionally cyano- or halogen-substituted C3-C6-alkenyl or C3-C6-alkynyl, or optionally cyano-, halogen- or C1-C4-alkyl-substituted C3-C6-cycloalkyl,
      • R17 represents hydrogen, optionally cyano-, hydroxyl-, halogen- or C1-C4-alkoxy-substituted C1-C6-alkyl, in each case optionally cyano- or halogen-substituted C3-C6-alkenyl or C3-C6-alkynyl, optionally cyano-, halogen- or C1-C4-alkyl-substituted C3-C6-cycloalkyl, or optionally nitro-, cyano-, halogen-, C1-C4-alkyl-, C1-C4-halogenoalkyl-, C1-C4-alkoxy- or C1-C4-halogenoalkoxy-substituted phenyl, or together with R16 represents in each case optionally C1-C4-alkyl-substituted C2-C6-alkanediyl or C2-C5-oxaalkanediyl.
      • X4 represents nitro, cyano, carboxyl, carbamoyl, formyl, sulphamoyl, hydroxyl, amino, halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy or C1-C4-haloalkoxy, and
      • X5 represents nitro, cyano, carboxyl, carbamoyl, formyl, sulphamoyl, hydroxyl, amino, halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy or C1-C4-haloalkoxy,
        where X4 is preferably located in position (2) and/or (5)
      • (“active compounds of group 2”).
  • In the definitions, the hydrocarbon chains, such as in alkyl or alkanediyl, are in each case straight-chain or branched—including in combination with hetero atoms, such as in alkoxy.
  • Preferred meanings of the groups listed above in connection with the formula (I) are defined below.
      • Q1 preferably represents O (oxygen) or S (sulphur).
      • Q2 preferably represents O (oxygen) or S (sulphur).
      • R1 preferably represents in each case optionally cyano-, fluorine-, chlorine-, methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, represents in each case optionally cyano-, fluorine- or chlorine-substituted propenyl, butenyl, propynyl or butynyl, represents in each case optionally cyano-, fluorine-, chlorine-, methyl- or ethyl-substituted cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl or cyclohexylmethyl, represents in each case optionally cyano-, fluorine-, chlorine-, bromine-, methyl-, ethyl-, n- or i-propyl-, trifluoromethyl-, methoxy-, ethoxy-, n- or i-propoxy-, difluoromethoxy- or trifluoromethoxy-substituted phenyl, phenylmethyl or phenylethyl, or represents in each case optionally cyano-, fluorine-, chlorine-, bromine-, methyl-, ethyl-, n- or i-propyl-, methoxy-, ethoxy-, n- or i-propoxy-substituted heterocyclyl or heterocyclylmethyl, where the heterocyclyl group is in each case selected from the group consisting of oxetanyl, thietanyl, furyl, tetrahydrofuryl, thienyl, tetrahydrothienyl.
      • R2 represents hydrogen, cyano, fluorine, chlorine, bromine, represents in each case optionally cyano-, fluorine-, chlorine-, methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, methylthio, ethylthio, n- or i-propylthio, methylsulphinyl, ethylsulphinyl, methylsulphonyl or ethylsulphonyl, or represents in each case optionally cyano-, fluorine- or chlorine-substituted propenyl, butenyl, propynyl, butynyl, propenyloxy, butenyloxy, propynyloxy or butynyloxy.
      • R3 represents hydrogen, hydroxyl, mercapto, amino, cyano, fluorine, chlorine, bromine, represents in each case optionally fluorine-, chlorine-, cyano-, methoxy-, ethoxy-, n- or i-propoxy-, acetyl-, propionyl-, n- or i-butyroyl, methoxycarbonyl-, ethoxycarbonyl-, n- or i-propoxycarbonyl-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, represents in each case optionally fluorine-, chlorine- and/or bromine-substituted ethenyl, propenyl, butenyl, ethynyl, propynyl or butynyl, represents in each case optionally fluorine-, chlorine-, cyano-, methoxy-, ethoxy-, n- or i-propoxy-, methoxycarbonyl-, ethoxycarbonyl-, n- or i-propoxycarbonyl-substituted methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, methylamino, ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino, acetylamino or propionylamino, represents propenyloxy, butenyloxy, ethynyloxy, propynyloxy, butynyloxy, propenylthio, butenylthio, propynylthio, butynylthio, propenylamino, butenylamino, propynylamino or butynylamino, represents dimethylamino, diethylamino or dipropylamino, represents in each case optionally fluorine-, chlorine-, methyl-and/or ethyl-substituted cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopentenyl, cyclohexenyl, cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy, cyclopropylthio, cyclobutylthio, cyclopentylthio, cyclohexylthio, cyclopropylamino, cyclobutylamino, cyclopentylamino, cyclohexylamino, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, cyclopropylmethoxy, cyclobutylmethoxy, cyclopentylmethoxy, cyclohexylmethoxy, cyclopropylmethylthio, cyclobutylmethylthio, cyclopentylmethylthio, cyclobexylmethylthio, cyclopropylmethylamino, cyclobutylmethylamino, cyclopentylmethylamino or cyclohexylmethylamino, or represents in each case optionally fluorine-, chlorine-, bromine-, methyl-, trifluoromethyl-, methoxy- or methoxycarbonyl-substituted phenyl, benzyl, phenoxy, benzyloxy, phenylthio, benzylthio, phenylamino or benzylamino.
      • R4 preferably represents hydrogen, hydroxyl, amino, represents in each case optionally fluorine-, chlorine-, cyano-, methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, represents in each case optionally fluorine, chlorine, and/or bromine-substituted ethenyl, propenyl, butenyl, propynyl or butynyl, represents in each case optionally fluorine-, chlorine-, cyano-, methoxy- or ethoxy-substituted methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methylamino, ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino, represents propenyloxy or butenyloxy, represents dimethylamino or diethylamino, represents in each case optionally fluorine-, chlorine-, methyl- and/or ethyl-substituted cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylamino, cyclobutylamino, cyclopentylamino, cyclohexylamino, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl or cyclohexylmethyl, or represents in each case optionally fluorine-, chlorine-, methyl-, trifluoromethyl- and/or methoxy-substituted phenyl or benzyl.
      • R3 and R4 together preferably represent trimethylene (propane-1,3-diyl), tetramethylene (butane-1,4-diyl) or pentamethylene (pentane-1,5-diyl).
      • Q1 particularly preferably represents O (oxygen).
      • Q2 particularly preferably represents O (oxygen).
      • R1 particularly preferably represents in each case optionally fluorine-, chlorine-, methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl.
      • R2 particularly preferably represents fluorine, chlorine, bromine or represents in each case optionally fluorine-, chlorine-, methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl.
      • R3 particularly preferably represents hydrogen, chlorine, bromine, represents in each case optionally fluorine-, chlorine-, methoxy-, ethoxy-, n- or i-propoxy-substituted methyl, ethyl, n- or i-propyl, represents in each case optionally fluorine- or chlorine-substituted ethenyl, propenyl, butenyl, propynyl or butynyl, represents in each case optionally fluorine-, chlorine-, methoxy-, ethoxy-, n- or i-propoxy-substituted methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylamino, ethylamino, n- or i-propylamino, represents propenyloxy, propynyloxy, propenylthio, propynylthio, propenylamino or propynylamino, represents dimethylamino or diethylamino, represents in each case optionally fluorine-, chlorine- or methyl-substituted cyclopropyl, cyclopropyloxy, cyclopropylmethyl or cyclopropylmethoxy.
      • R4 particularly preferably represents in each case optionally fluorine-, chlorine-, methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl, represents in each case optionally fluorine- or chlorine-substituted ethenyl, propenyl or propynyl, represents in each case optionally fluorine-, chlorine-, methoxy- or ethoxy-substituted methoxy, ethoxy, n- or i-propoxy, represents methylamino, or represents cyclopropyl.
  • Most preferably, R1 and R2 represent methyl, ethyl, n- or i-propyl.
  • Preferred active compound components of group 1 are in particular also the sodium, potassium, magnesium, calcium, ammonium, C1-C4-alkylammonium-, di-(C1-C4-alkyl)ammonium-, tri-(C1-C4-alkyl)ammonium, tetra-(C1-C4-alkyl)ammonium, tri-(C1-C4-alkyl)sulphonium-, C5- or C6-cycloalkylammonium and di-(C1-C2-alkyl)-benzylammonium salts of compounds of the formula (I) in which Q1, Q2, R1, R2, R3 and R4 have the meanings given above as being preferred.
  • Examples of compounds of the formula (I) which are very particularly preferred as active compound components according to the invention are listed in Table 1 below.
    TABLE 1
    (I)
    Figure US20050009705A1-20050113-C00009
    Examples of compounds of the formula (I)
    Melting
    Ex. No. Q1 Q2 R1 R2 R3 R4 point (° C.)
    I-1  O O CH3 CH3 OC2H5 CH3 163
    I-2  O O CH3 CH3 OCH3 CH3 201
    I-3  O O CH3 CH3 OC3H7-n CH3 156
    I-4  O O CH3 CH3 OC3H7-i CH3 150
    I-5  O O CH3 CH3 OCH3
    Figure US20050009705A1-20050113-C00010
         		218
    I-6  O O CH3 CH3 OC2H5
    Figure US20050009705A1-20050113-C00011
         		170
    I-7  O O CH3 CH3 OC3H7-n
    Figure US20050009705A1-20050113-C00012
         		156
    I-8  O O CH3 CH3 OC3H3-i
    Figure US20050009705A1-20050113-C00013
         		188
    I-9  O O CH3 CH3
    Figure US20050009705A1-20050113-C00014
    Figure US20050009705A1-20050113-C00015
         		200
    I-10 O O CH3 CH3 CH3 CH3 178
    I-11 O O CH3 CH3 C2H5 CH3 161
    I-12 O O CH3 CH3 SCH3 CH3 183
    I-13 O O C2H5 CH3 OCH3 CH3 176
    I-14 O O CH3 CH3 CH2OCH3
    Figure US20050009705A1-20050113-C00016
         		185
    I-15 O O C2H5 CH3 OC2H5 CH3 172
    I-16 O O C2H5 CH3 OCH3
    Figure US20050009705A1-20050113-C00017
         		173
    I-17 O O CH3 CH3 C2H5 OC2H5 183
    I-18 O O CH3 CH3 C2H5
    Figure US20050009705A1-20050113-C00018
         		175
  • Very particular emphasis as active compound components according to the invention is also given to the sodium salts of the compounds from Table 1.
  • Preferred meanings of the groups listed above in connection with the compounds improving crop plant compatibility (“herbicide safeners”) of the formulae (Ia), (IIb), (IIc), (IId) and (IIe) are defined below.
      • n preferably represents the numbers 0, 1, 2, 3 or 4.
      • A2 preferably represents in each case optionally methyl-, ethyl-, methoxycarbonyl- or ethoxycarbonyl-substituted methylene or ethylene.
      • R5 preferably represents hydroxyl, mercapto, amino, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, methylamino, ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino, dimethylamino or diethylamino.
      • R6 preferably represents hydroxyl, mercapto, amino, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, methylamino, ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino, dimethylamino or diethylamino.
      • R7 preferably represents in each case optionally fluorine-, chlorine- and/or bromine-substituted methyl, ethyl, n- or i-propyl.
      • R8 preferably represents hydrogen, in each case optionally fluorine- and/or chlorine-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, propenyl, butenyl, propynyl or butynyl, methoxymethyl, ethoxymethyl, methoxyethyl, ethoxyethyl, dioxolanylmethyl, furyl, furylmethyl, thienyl, thiazolyl, piperidinyl, or optionally fluorine-, chlorine-, methyl-, ethyl-, n- or i-propyl-, n-, i-, s- or t-butyl-substituted phenyl.
      • R9 preferably represents hydrogen, in each case optionally fluorine- and/or chlorine-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, propenyl, butenyl, propynyl or butynyl, methoxymethyl, ethoxymethyl, methoxyethyl, ethoxyethyl, dioxolanylmethyl, furyl, furylmethyl, thienyl, thiazolyl, piperidinyl, or optionally fluorine-, chlorine-, methyl-, ethyl-, n- or i-propyl-, n-, 30 i-, s- or t-butyl-substituted phenyl, or together with R8 represents one of the radicals —CH2—O—CH2-CH2— and —CH2-CH2—O—CH2-CH2—, which are optionally substituted by methyl, ethyl, furyl, phenyl, a fused-on benzene ring or by two substituents which together with the C atom to which they are attached form a 5- or 6-membered carbocycle.
      • R10 preferably represents hydrogen, cyano, fluorine, chlorine, bromine, or represents in each case optionally fluorine-, chlorine- and/or bromine-substituted methyl, ethyl, n- or i-propyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl or phenyl.
      • R11 preferably represents hydrogen, optionally hydroxyl-, cyano-, fluorine-, chlorine-, methoxy-, ethoxy-, n- or i-propoxy-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl.
      • R12 preferably represents hydrogen, cyano, fluorine, chlorine, bromine, or represents in each case optionally fluorine-, chlorine- and/or bromine-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl or phenyl.
      • X1 preferably represents nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, difluoromethyl, dichloromethyl, trifluoromethyl, trichloromethyl, chlorodifluoromethyl, fluorodichloromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy or trifluoromethoxy.
      • X2 preferably represents hydrogen, nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, difluoromethyl, dichloromethyl, trifluoromethyl, trichloromethyl, chlorodifluoromethyl, fluorodichloromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy or trifluoromethoxy.
      • X3 preferably represents hydrogen, nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, difluoromethyl, dichloromethyl, trifluoromethyl, trichloromethyl, chlorodifluoromethyl, fluorodichloromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy or trifluoromethoxy.
      • R13 preferably represents hydrogen, methyl, ethyl, n- or i-propyl.
      • R14 preferably represents hydrogen, methyl, ethyl, n- or i-propyl.
      • R15 preferably represents hydrogen, in each case optionally cyano-, fluorine-, chlorine-, methoxy-, ethoxy-, n- or i-propoxy-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, methylamino, ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino, dimethylamino or diethylamino, or in each- case optionally cyano-, fluorine-, chlorine-, bromine-, methyl-, ethyl-, n- or i-propyl-substituted cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy, cyclopropylthio, cyclobutylthio, cyclopentylthio, cyclohexylthio, cyclopropylamino, cyclobutylamino, cyclopentylamino or cyclohexylamino.
      • R16 preferably represents hydrogen, in each case optionally cyano-, hydroxyl-, fluorine-, chlorine-, methoxy-, ethoxy-, n- or i-propoxy-substituted methyl, ethyl, n- or i-propyl, n-, i- or s-butyl, in each case optionally cyano-, fluorine-, chlorine- or bromine-substituted propenyl, butenyl, propynyl or butynyl, or in each case optionally cyano-, fluorine-, chlorine-, bromine-, methyl-, ethyl-, n- or i-propyl-substituted cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl.
      • R17 preferably represents hydrogen, represents in each case optionally cyano-, hydroxyl-, fluorine-, chlorine-, methoxy-, ethoxy-, n- or i-propoxy-substituted methyl, ethyl, n- or i-propyl, n-, i- or s-butyl, in each case optionally cyano-, fluorine-, chlorine- or bromine-substituted propenyl, butenyl, propynyl or butynyl, in each case optionally cyano-, fluorine-, chlorine-, bromine-, methyl-, ethyl-, n- or i-propyl-substituted cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl, or optionally nitro-, cyano-, 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, or together with R16 represents in each case optionally methyl- or ethyl-substituted butane-1,4-diyl (trimethylene), pentane-1,5-diyl, 1-oxa-butane-1,4-diyl or 3-oxa-pentane-1,5-diyl.
      • X4 preferably represents nitro, cyano, carboxyl, carbamoyl, formyl, sulphamoyl, hydroxyl, amino, 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.
      • X5 preferably represents nitro, cyano, carboxyl, carbamoyl, formyl, sulphamoyl, hydroxyl, amino, 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.
  • Examples of compounds of the formula (IIa) which are very particularly preferred as herbicide safeners according to the invention are listed in Table 2 below.
  • Table 2: Examples of the compounds of the formula (IIa)
    (IIa)
    Figure US20050009705A1-20050113-C00019
    Example No. (positions) (X1)n A1 R5
    IIa-1 (2) Cl, (4) Cl
    Figure US20050009705A1-20050113-C00020
         		OCH3
    IIa-2 (2) Cl, (4) Cl
    Figure US20050009705A1-20050113-C00021
         		OCH3
    IIa-3 (2) Cl, (4) Cl
    Figure US20050009705A1-20050113-C00022
         		OC2H5
    IIa-4 (2) Cl, (4) Cl
    Figure US20050009705A1-20050113-C00023
         		OC2H5
    IIa-5 (2) Cl
    Figure US20050009705A1-20050113-C00024
         		OCH3
    IIa-6 (2) Cl, (4) Cl
    Figure US20050009705A1-20050113-C00025
         		OCH3
    IIa-7 (2) F
    Figure US20050009705A1-20050113-C00026
         		OCH3
    IIa-8 (2) F
    Figure US20050009705A1-20050113-C00027
         		OCH3
    IIa-9 (2) Cl, (4) Cl
    Figure US20050009705A1-20050113-C00028
         		OC2H5
    IIa-10 (2) Cl, (4) CF3
    Figure US20050009705A1-20050113-C00029
         		OCH3
    IIa-11 (2) Cl
    Figure US20050009705A1-20050113-C00030
         		OCH3
    IIa-12 —
    Figure US20050009705A1-20050113-C00031
         		OC2H5
    IIa-13 (2) Cl, (4) Cl
    Figure US20050009705A1-20050113-C00032
         		OC2H5
    IIa-14 (2) Cl, (4) Cl
    Figure US20050009705A1-20050113-C00033
         		OC2H5
    IIa-15 (2) Cl, (4) Cl
    Figure US20050009705A1-20050113-C00034
         		OC2H5
    IIa-16 (2) Cl, (4) Cl
    Figure US20050009705A1-20050113-C00035
         		OC2H5
    IIa-17 (2) Cl, (4) Cl
    Figure US20050009705A1-20050113-C00036
         		OC2H5
  • Examples of compounds of the formula (IIb) which are very particularly preferred as herbicide safeners according to the invention are listed in Table 3 below.
    TABLE 3
    (IIb)
    Figure US20050009705A1-20050113-C00037
    Examples of compounds of the formula (IIb)
    Example No. (position) X2 (position) X3 A2 R6
    IIb-1 (5) Cl — CH2 OH
    IIb-2 (5) Cl — CH2 OCH2
    IIb-3 (5) Cl — CH2 OC2H5
    IIb-4 (5) Cl — CH2 OC3H7-n
    IIb-5 (5) Cl — CH2 OC3H7-i
    IIb-6 (5) Cl — CH2 OC4H9-n
    IIb-7 (5) Cl — CH2 OCH(CH3)C5H11-n
    IIb-8 (5) Cl (2) F CH2 OH
    IIb-9 (5) Cl (2) Cl CH2 OH
    IIb-10 (5) Cl — CH2 OCH2CH═CH2
    IIb-11 (5) Cl — CH2 OC4H9-i
    IIb-12 (5) Cl — CH2
    Figure US20050009705A1-20050113-C00038
    IIb-13 (5) Cl —
    Figure US20050009705A1-20050113-C00039
         		OCH2CH═CH2
    IIb-14 (5) Cl —
    Figure US20050009705A1-20050113-C00040
         		OC2H5
  • Examples of the compounds (IIc) which are very particularly preferred as herbicide safeners according to the invention are listed in Table 4 below.
    TABLE 4
    (IIc)
    Figure US20050009705A1-20050113-C00041
    Examples of the compounds of the formula (IIc)
    Example No. R7 N(R8R9)
    IIc-1 CHCl2 N(CH2CH═CH2)2
    IIc-2 CHCl2
    Figure US20050009705A1-20050113-C00042
    IIc-3 CHCl2
    Figure US20050009705A1-20050113-C00043
    IIc-4 CHCl2
    Figure US20050009705A1-20050113-C00044
    IIc-5 CHCl2
    Figure US20050009705A1-20050113-C00045
    IIc-6 CHCl2
    Figure US20050009705A1-20050113-C00046
    IIc-7 CHCl2
    Figure US20050009705A1-20050113-C00047
  • Examples of the compounds of the formula (IId) which are very particularly preferred as herbicide safeners according to the invention are listed in Table 5 below.
    TABLE 5
    (IId)
    Figure US20050009705A1-20050113-C00048
    Examples of the compounds of the formula (IId)
    Example (positions) (positions)
    No. R13 R14 R15 (X4)n (X5)n
    IId-1 H H CH3 (2) OCH3 —
    IId-2 H H C2H5 (2) OCH3 —
    IId-3 H H C3H7-n (2) OCH3 —
    IId-4 H H C3H7-i (2) OCH3 —
    IId-5 H H
    Figure US20050009705A1-20050113-C00049
         		(2) OCH3 —
    IId-6 H H CH3 (2) OCH3 (5) CH3 —
    IId-7 H H C2H5 (2) OCH3 (5) CH3 —
    IId-8 H H C3H7-n (2) OCH3 (5) CH3 —
    IId-9 H H C3H7-i (2) OCH3 (5) CH3 —
    IId-10 H H
    Figure US20050009705A1-20050113-C00050
         		(2) OCH3 (5) CH3 —
    IId-11 H H OCH3 (2) OCH3 (5) CH3 —
    IId-12 H H OC2H5 (2) OCH3 (5) CH3 —
    lId-13 H H OC3H7-i (2) OCH3 (5) CH3 —
    IId-14 H H SCH3 (2) OCH3 (5) CH3 —
    IId-15 H H SC2H5 (2) OCH3 (5) CH3 —
    IId-16 H H SC3H7-i (2) OCH3 (5) CH3 —
    Ild-17 H H NHCH3 (2) OCH3 (5) CH3 —
    lId-18 H H NHC2H5 (2) OCH3 (5) CH3 —
    IId-19 H H NHC3H7-i (2) OCH3 (5) CH3 —
    IId-20 H H
    Figure US20050009705A1-20050113-C00051
         		(2) OCH3 (5) CH3 —
    IId-21 H H NHCH3 (2) OCH3 —
    IId-22 H H NHC3H7-i (2) OCH3 —
    IId-23 H H N(CH3)2 (2) OCH3 —
    IId-24 H H N(CH3)2 (2) OCH3 (5) CH3 —
    IId-25 H H CH2OCH3 (2) OCH3 —
    IId-26 H H CH2OCH3 (2) OCH3 (5) CH3 —
  • Examples of the compounds of the formula (IIe) which are very particularly preferred as herbicide safeners according to the invention are listed in Table 6 below.
    TABLE 6
    (IIe)
    Figure US20050009705A1-20050113-C00052
    Examples of the compounds of the formula (IIe)
    Example (positions) (positions)
    No. R13 R16 R17 (X4)n (X5)n
    IIe-1 H H CH3 (2) OCH3 —
    IIe-2 H H C2H5 (2) OCH3 —
    IIe-3 H H C3H7-n (2) OCH3 —
    IIe-4 H H C3H7-i (2) OCH3 —
    IIe-5 H H
    Figure US20050009705A1-20050113-C00053
         		(2) OCH3 —
    IIe-6 H CH3 CH3 (2) OCH3 —
    IIe-7 H H CH3 (2) OCH3 —
    (5) CH3
    IIe-8 H H C2H5 (2) OCH3 —
    (5) CH3
    IIe-9 H H C3H7-n (2) OCH3 —
    (5) CH3
    IIe-10 H H C3H7-i (2) OCH3 —
    (5) CH3
    IIe-11 H H
    Figure US20050009705A1-20050113-C00054
         		(2) OCH3 (5) CH 3 —
    IIe-12 H CH3 CH3 (2) OCH3 —
    (5) CH3
    IIe-13 H H CH2CH═CH2 (2) OCH3 —
    IIe-14 H H CH2CH═CH2 (2) OCH3 —
    (5) CH3
    IIe-15 H H
    Figure US20050009705A1-20050113-C00055
         		(2) OCH3 —
    IIe-16 H H
    Figure US20050009705A1-20050113-C00056
         		(2) OCH3 (5) CH 3 —
    Ile-17 H H
    Figure US20050009705A1-20050113-C00057
         		(2) OCH3 —
    IIe-18 H H
    Figure US20050009705A1-20050113-C00058
         		(2) OCH3 (5) CH 3 —
    IIe-19 H H
    Figure US20050009705A1-20050113-C00059
         		(2) OCH3 —
    IIe-20 H H
    Figure US20050009705A1-20050113-C00060
         		(2) OCH3 (5) CH 3 —
  • The compounds of the general formula (IIa) to be used as safeners according to the invention are known and/or can be prepared by processes known per se (cf. WO-A-91/07874, WO-A-95/07897).
  • The compounds of the general formula (IIb) to be used as safeners according to the invention are known and/or can be prepared by processes known per se (cf. EP-A-191736).
  • The compounds of the general formula (IIc) to be used as safeners according to the invention are known and/or can be prepared by processes known per se (cf. DE-A-22180974, DE-A-2350547).
  • The compounds of the general formula (IId) to be used as safeners according to the invention are known and/or can be prepared by processes known per se (cf. DE-A-19621522/U.S. Pat. No. 6,235,680/WO 97/45016).
  • The compounds of the general formula (IIe) to be used as safeners according to the invention are known and/or can be prepared by processes known per se (cf. WO-A-99/66795/U.S. Pat. No. 6,251,827).
  • Examples of the selectively herbicidal combinations according to the invention of in each case one active compound of the formula (I) and in each case one of the safeners defined above are listed in Table 7 below.
    TABLE 7
    Examples of combinations according to the invention
    Active compound of
    the formula (I) Safener
    I-1 AD-67
    I-1 cloquintocet-mexyl
    I-1 dichlormid
    I-1 fenchlorazole-ethyl
    I-1 isoxadifen-ethyl
    I-1 mefenpyr-diethyl
    I-1 MON-7400
    I-1 flurazole
    I-1 furilazole
    I-1 fenclorim
    I-1 cumyluron
    I-1 daimuron/dymron
    I-1 dimepiperate
    I-1 IId-25
    I-1 IIe-11
    I-2 AD-67
    I-2 cloquintocet-mexyl
    I-2 dichlormid
    I-2 fenchlorazole-ethyl
    I-2 isoxadifen-ethyl
    I-2 mefenpyr-diethyl
    I-2 MON-7400
    I-2 flurazole
    I-2 furilazole
    I-2 fenclorim
    I-2 cumyluron
    I-2 daimuron/dymron
    I-2 dimepiperate
    I-2 IId-25
    I-2 IIe-11
    I-3 AD-67
    I-3 cloquintocet-mexyl
    I-3 dichlormid
    I-3 fenchlorazole-ethyl
    I-3 isoxadifen-ethyl
    I-3 mefenpyr-diethyl
    I-3 MON-7400
    I-3 flurazole
    I-3 furilazole
    I-3 fenclorim
    I-3 cumyluron
    I-3 daimuron/dymron
    I-3 dimepiperate
    I-3 IId-25
    I-3 IIe-11
    I-4 AD-67
    I-4 cloquintocet-mexyl
    I-4 dichlormid
    I-4 fenchlorazole-ethyl
    I-4 isoxadifen-ethyl
    I-4 mefenpyr-diethyl
    I-4 MON-7400
    I-4 flurazole
    I-4 furilazole
    I-4 fenclorim
    I-4 cumyluron
    I-4 daimuron/dymron
    I-4 dimepiperate
    I-4 IId-25
    I-4 IIe-11
    I-5 AD-67
    I-5 cloquintocet-mexyl
    I-5 dichlormid
    I-5 fenchlorazole-ethyl
    I-5 isoxadifen-ethyl
    I-5 mefenpyr-diethyl
    I-5 MON-7400
    I-5 flurazole
    I-5 furilazole
    I-5 fenclorim
    I-5 cumyluron
    I-5 daimuron/dymron
    I-5 dimepiperate
    I-5 IId-25
    I-5 IIe-11
    I-6 AD-67
    I-6 cloquintocet-mexyl
    I-6 dichlormid
    I-6 fenchlorazole-ethyl
    I-6 isoxadifen-ethyl
    I-6 mefenpyr-diethyl
    I-6 MON-7400
    I-6 flurazole
    I-6 furilazole
    I-6 fenclorim
    I-6 cumyluron
    I-6 daimuron/dymron
    I-6 dimepiperate
    I-6 IId-25
    I-6 IIe-11
    I-7 AD-67
    I-7 cloquintocet-mexyl
    I-7 dichlormid
    I-7 fenchlorazole-ethyl
    I-7 isoxadifen-ethyl
    I-7 mefenpyr-diethyl
    I-7 MON-7400
    I-7 flurazole
    I-7 furilazole
    I-7 fenclorim
    I-7 cumyluron
    I-7 daimuron/dymron
    I-7 dimepiperate
    I-7 IId-25
    I-7 IIe-11
    I-8 AD-67
    I-8 cloquintocet-mexyl
    I-8 dichlormid
    I-8 fenchlorazole-ethyl
    I-8 isoxadifen-ethyl
    I-8 mefenpyr-diethyl
    I-8 MON-7400
    I-8 flurazole
    I-8 furilazole
    I-8 fenclorim
    I-8 cumyluron
    I-8 daimuron/dymron
    I-8 dimepiperate
    I-8 IId-25
    I-8 IIe-11
    I-9 AD-67
    I-9 cloquintocet-mexyl
    I-9 dichlormid
    I-9 fenchlorazole-ethyl
    I-9 isoxadifen-ethyl
    I-9 mefenpyr-diethyl
    I-9 MON-7400
    I-9 flurazole
    I-9 furilazole
    I-9 fenclorim
    I-9 cumyluron
    I-9 daimuron/dymron
    I-9 dimepiperate
    I-9 IId-25
    I-9 IIe-11
    I-10 AD-67
    I-10 Cloquintocet-mexyl
    I-10 dichlormid
    I-10 fenchlorazole-ethyl
    I-10 isoxadifen-ethyl
    I-10 mefenpyr-diethyl
    I-10 MON-7400
    I-10 flurazole
    I-10 furilazole
    I-10 fenclorim
    I-10 cumyluron
    I-10 daimuron/dymron
    I-10 dimepiperate
    I-10 IId-25
    I-10 IIe-11
    I-11 AD-67
    I-11 cloquintocet-mexyl
    I-11 dichlormid
    I-11 fenchlorazole-ethyl
    I-11 isoxadifen-ethyl
    I-11 mefenpyr-diethyl
    I-11 MON-7400
    I-11 flurazole
    I-11 furilazole
    I-11 fenclorim
    I-11 cumyluron
    I-11 daimuron/dymron
    I-11 dimepiperate
    I-11 IId-25
    I-11 IIe-11
    I-12 AD-67
    I-12 cloquintocet-mexyl
    I-12 dichlormid
    I-12 fenchlorazole-ethyl
    I-12 isoxadifen-ethyl
    I-12 mefenpyr-diethyl
    I-12 MON-7400
    I-12 flurazole
    I-12 furilazole
    I-12 fenclorim
    I-12 cumyluron
    I-12 daimuron/dymron
    I-12 dimepiperate
    I-12 IId-25
    I-12 IIe-11
    I-13 mefenpyr-diethyl
    I-2, sodium salt IId-25
    I-15 mefenpyr-diethyl
    I-16 mefenpyr-diethyl
    I-17 mefenpyr-diethyl
    I-14 mefenpyr-diethyl
    I-18 mefenpyr-diethyl
  • Surprisingly, it has now been found that the above-defined active compound combinations of substituted thien-3-ylsulphonylamino(thio)carbonyltriazolin(ethi)ones of the general formula (I) and/or their salts and safeners (antidotes) of group (2) listed above, whilst being tolerated very well by crop plants, have particularly high herbicidal activity and can be used in various crops, in particular in cereal (especially wheat) and maize, but also in soya beans, potatoes and rice, for the selective control of weeds.
  • Here, it has to be considered to be surprising that, from a large number of known safeners or antidotes which are capable of antagonizing the damaging effect of a herbicide on the crop plants, that are in particular the abovementioned compounds of group (2) which neutralize the damaging—effect of substituted thien-3-ylsulphonylamino(thio)carbonyltriazolin(ethi)ones on the crop plants virtually completely without negatively affecting the herbicidal activity with respect to the weeds.
  • Emphasis is given here to the particularly advantageous effect of the particularly and most preferred combination partners from group (2), in particular in respect of sparing cereal plants, such as, for example, wheat, barley and rye, but also maize and rice, as crop plants.
  • The active compound combinations according to the invention can be used, for example, in connection with the following plants:
      • Dicotyledonous weeds 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, Veronica, Abutilon, Emex, Datura, Viola, Galeopsis, Papaver, Centaurea, Trifolium, Ranunculus, Taraxacum.
      • Dicotyledonous crops of the genera: Gossypium, Glycine, Beta, Daucus, Phaseolus, Pisum, Solanum, Linum, Ipomoea, Vicia, Nicotiana, Lycopersicon, Arachis, Brassica, Lactuca, Cucumis, Cuburbita, Helianthus.
      • Monocotyledonous weeds 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, Ischaemum, Sphenoclea, Dactyloctenium, Agrostis, Alopecurus, Apera.
      • Monocotyledonous crops of the genera: Oryza, Zea, Triticum, Hordeum, Avena, Secale, Sorghum, Panicum, Saccharum, Ananas, Asparagus, Allium.
  • However, the use of the active compound combinations according to the invention is in no way restricted to these genera, but also extends in the same manner to other plants. According to the invention, crop plants are all plants and plant varieties including transgenic plants and plant varieties, where on transgenic plants and plant varieties it is also possible for synergistic effects to occur.
  • The advantageous effect of the crop plant compatibility of the active compound combinations according to the invention is particularly highly pronounced at certain concentration ratios. However, the weight ratios of the active compounds in the active compound concentrations can be varied within relatively wide ranges. In general, 0.001 to 1000 parts by weight, preferably 0.01 to 100 parts by weight, and particularly preferably 0.1 to 50 parts by weight and most preferably 1 to 25 parts by weight of one of the compounds which improve crop plant compatibility mentioned under group 2 above (antidotes/safeners) are present per part by weight of active compound of the formula (I) or its salts.
  • The active compounds or active compound combinations can be converted into the customary formulations, such as solutions, emulsions, wettable powders, suspensions, powders, dusting agents, pastes, soluble powders, granules, suspoemulsion concentrates, natural and synthetic materials impregnated with active compound, and very fine capsules in polymeric substances.
  • These formulations are produced in a known manner, for example by mixing the active compounds with extenders, that is liquid solvents and/or solid carriers, optionally with the use of surfactants, that is emulsifiers and/or dispersants and/or foam-formers.
  • If the extender used is water, it is also possible to use, for example, organic solvents as auxiliary solvents. Suitable liquid solvents are essentially: aromatics, such as xylene. toluene or alkylnaphthalenes, chlorinated aromatics and chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chloroethylenes or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, for example petroleum fractions, mineral and vegetable oils, alcohols, such as butanol or glycol, and also their ethers and esters, ketones, such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents, such as dimethylformamide and dimethyl sulphoxide, and also water.
  • Suitable solid carriers are:
      • for example ammonium salts and ground natural minerals, such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, ground synthetic minerals, such as finely divided silica, alumina and silicates, suitable solid carriers for granules are: for example crushed and fractionated natural rocks such as calcite, marble, pumice, sepiolite and dolomite, and also synthetic granules of inorganic and organic meals, and granules of organic material such as sawdust, coconut shells, maize cobs and tobacco stalks; suitable emulsifiers and/or foam-formers are: for example non-ionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example alkylaryl polyglycol ethers, alkylsulphonates, alkyl sulphates, arylsulphonates and protein hydrolysates; suitable dispersants are: for example lignosulphite waste liquors and methylcellulose.
  • Tackifiers such as carboxymethylcellulose and natural and synthetic polymers in the form of powders, granules or latices, such as gum arabic, polyvinyl alcohol and polyvinyl acetate, and also natural phospholipids, such as cephalins and lecithins, and synthetic phospholipids, can be used in the formulations. Other possible additives are mineral and vegetable oils.
  • It is possible to use colorants such as inorganic pigments, for example iron oxide, titanium oxide and Prussian Blue, and organic dyestuffs, such as alizarin dyestuffs, azo dyestuffs and metal phthalocyanine dyestuffs, and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.
  • The formulations generally comprise from 0.1 to 95 per cent by weight of active compounds including the safeners, preferably between 0.5 and 90%.
  • The active compound combinations according to the invention are generally used in the form of finished formulations. However, the active compounds contained in the active compound combinations can also be mixed in individual formulations when used, i.e. in the form of tank mixes.
  • The novel active compound combinations, as such or in their formulations, can furthermore be used as a mixture with other known herbicides, finished formulations or tank mixes again being possible. A mixture with other known active compounds, such as fungicides, insecticides, acaricides, nematicides, bird repellents, growth factors, plant nutrients and agents which improve soil structure, is also possible. For certain intended uses, in particular in the post-emergence method, it may furthermore be advantageous to include, as further additives in the formulations, mineral or vegetable oils which are tolerated by plants (for example the commercial preparation “Rako Binol”), or ammonium salts such as, for example, ammonium sulphate or ammonium thiocyanate.
  • The novel active compound combinations 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. They are used in the customary manner, for example by washing, spraying, atomizing, dusting or scattering.
  • The amounts of the active compound combinations according to the invention applied can be varied within a certain range; they depend, inter alia. on the weather and on soil factors. In general, the application rates are between 0.001 and 5 kg per ha, preferably between 0.001 and 1 kg per ha, particularly preferably between 0.003 and 0.5 kg per ha.
  • The active compound combinations according to the invention can be applied before and after emergence of the plants, that is to say by the pre-emergence and post-emergence method.
    • USE EXAMPLES
  • The active compound or safener components are in each case dissolved in a few ml (generally 2-3 ml) of solvent (generally acetone or N,N-dimethyl-formamide), and the solutions are combined and then—if appropriate after addition of an emulsifier—diluted with water to the desired concentration. In general, an aqueous spray liquor was prepared using 0.1% of the additive Renex-36.
    • Example A
  • Post-Emergence Test
  • The test plants are grown under controlled conditions (temperature, light, atmospheric humidity) in a greenhouse. The test plants are sprayed when they have reached a height of 5-15 cm. The concentration of the spray liquor is chosen such that the particular amounts of active compound desired are applied in 500 l of water/ha.
  • After spraying, the pots with the test plants are kept in a greenhouse chamber under controlled conditions (temperature, light, atmospheric humidity) until the test has ended. About three weeks after the application, the degree of damage to the crop plants is rated in % damage in comparison to the development of the untreated control.
  • The figures denote:
      • 0%=no damage (like untreated control)
      • 100%=total destruction/damage
  • Active compounds, application rates, test plants and results are shown in the tables below, the terms being used in the tables being as defined below:
      • maize=maize cv. “Pioneer”
  • a.i.=active ingredient=active compound/safener
    TABLE A1
    Post-emergence test/greenhouse
    Active compound Application rate Damage maize
    (+ safener) (g of a.i./ha) (in %)
    I-2 10 35
    I-2 + AD-67 10 + 100 7
    I-2 + cloquintocet-mexyl 10 + 100 1.5
    I-2 + dichlormid 10 + 100 13.5
    I-2 + fenchlorazole-ethyl 10 + 100 12
    I-2 + isoxadifen-ethyl 10 + 100 4
    I-2 + furilazole 10 + 100 2.5
    I-2 + flurazole 10 + 100 4.5
    I-2 + IIe-11 10 + 100 2
    I-2 + MON-7400 10 + 100 1.5
    • Example A-2
  • Post-Emergence Test
  • Here, an aqueous spray liquor comprising 0.5% of the additive Renex-36 was prepared.
  • Ex. No. I-2, sodium salt=
    Figure US20050009705A1-20050113-C00061
  • Ex.-No. IId-25=
    Figure US20050009705A1-20050113-C00062
    TABLE A-2-1
    Post-emergence test/greenhouse
    Damage
    winter
    Active compound Application rate barley
    (+ safener) (g of a.i./ha) (in %)
    I-2, sodium salt 4 60
    2 50
    I-2, sodium salt +     4 + 100 50
    Comp. No. IId-25     2 + 100 25
       4 + 30 50
       2 + 30 35
  • TABLE A-2-2
    Post-emergence test/greenhouse
    Damage
    winter
    Application rate barley
    Safener (g of a.i./ha) (in %)
    Comp. No. IId-25 100 0
    30 0
    • Example A-3
  • Post-Emergence Test
  • The compound I-2 was used as 10 WP. In each case, Marlipal® was added in an amount of 500 ml/ha.
  • Evaluation was carried out as early as 7 days after the application.
  • Maize 1=maize of the cultivar “Prinz”
  • Maize 2=maize of the cultivar “Pioneer”
  • Maize 3=maize of the cultivar “LIXIS”
    TABLE A-3-1
    Post-emergence test/greenhouse
    Damage
    Application rate maize 1
    Active compound (+ safener) (g of a.i./ha) (in %)
    I-2 15 20
    8 10
    I-2 + Comp. No. IId-25 15 + 100 5
     8 + 100 0
  • TABLE A-3-2
    Post-emergence test/greenhouse
    Damage
    Application rate maize 2
    Active compound (+ safener) (g of a.i./ha) (in %)
    I-2 15 20
    8 10
    I-2 + Comp. No. IId-25 15 + 100 5
     8 + 100 5
  • TABLE A-3-3
    Post-emergence test/greenhouse
    Application rate Damage
    Active compound (+ safener) (g of a.i./ha) Maize 3 (in %)
    I-2 15 40
    8 20
    I-2 + Comp. No. IId-25 15 + 100 20
     8 + 100 10
    15 + 50  10
     8 + 50  10
    • Example A-4
  • Post-Emergence Test
  • Mefenpyr-diethyl was used as 100 EC.
  • The compounds of Ex. Nos. I-2 and I-13 were used as 10 WP.
    TABLE A-4-1
    Post-emergence test/greenhouse
    Application rate Damage winter
    Safener (g of a.i./ha) wheat (in %)
    mefenpyr-diethyl 50 0
  • TABLE A-4-2
    Post-emergence test/greenhouse
    Application rate Damage winter
    Active compound (+ safener) (g of a.i./ha) wheat (in %)
    I-2 30 60
    15 40
    I-2 + mefenpyr-diethyl 30 + 50 10
    15 + 50 5
  • TABLE A-4-3
    Post-emergence test/greenhouse
    Damage winter
    Application rate wheat
    Active compound (+ safener) (g of a.i./ha) (in %)
    I-13 125 30
    60 20
    I-13 + mefenpyr-diethyl 125 + 50 10
     60 + 50 5
  • TABLE A-4-4
    Post-emergence test/greenhouse
    Damage winter
    Application rate wheat
    Safener (g of a.i./ha) (in %)
    mefenpyr-diethyl 50 0
  • TABLE A-4-5
    Post-emergence test/greenhouse
    Damage winter
    Application rate barley
    Active compound (+ safener) (g of a.i./ha) (in %)
    I-2 30 80
    15 70
    8 50
    I-2 + mefenpyr-diethyl 30 + 50 70
    15 + 50 40
     8 + 50 30
  • TABLE A-4-6
    Post-emergence test/greenhouse
    Application rate Damage winter
    Active compound (+ safener) (g of a.i./ha) barley (in %)
    I-13 125 80
    60 70
    30 50
    I-13 + mefenpyr-diethyl 125 + 50 60
     60 + 50 50
     30 + 50 30
    • Example A-5
  • Post-Emergence Test
  • Mefenpyr-diethyl was used as 100 EC and the compound of Ex. No. I-2 was used as 10 WP.
    TABLE A-5-1
    Post-emergence test/greenhouse
    Application rate Damage winter
    Active compound (+ safener) (g of a.i./ha) wheat (in %)
    I-2 30 60
    mefenpyr-diethyl 50 0
    I-2 + mefenpyr-diethyl 30 + 50 5
  • TABLE A-5-2
    Post-emergence test/greenhouse
    Application rate Damage winter
    Active compound (+ safener) (g of a.i./ha) wheat (in %)
    I-13 125 50
    mefenpyr-diethyl 50 0
    I-13 + mefenpyr-diethyl 125 + 50 10
  • TABLE A-5-3
    Post-emergence test/greenhouse
    Application rate Damage winter
    Active compound (+ safener) (g of a.i./ha) wheat (in %)
    I-15 60 80
    mefenpyr-diethyl 50 0
    I-15 + mefenpyr-diethyl 60 + 50 40
  • TABLE A-5-4
    Post-emergence test/greenhouse
    Application rate Damage winter
    Active compound (+ safener) (g of a.i./ha) wheat (in %)
    I-16 60 25
    mefenpyr-diethyl 50 0
    I-16 + mefenpyr-diethyl 60 + 50 15
  • TABLE A-5-5
    Post-emergence test/greenhouse
    Application rate Damage winter
    Safener (g of a.i./ha) wheat (in %)
    mefenpyr-diethyl 50 0
  • TABLE A-5-6
    Post-emergence test/greenhouse
    Application rate Damage winter
    Active compound (+ safener) (g of a.i./ha) wheat (in %)
    I-2 30 40
    15 30
    8 20
    I-2 + mefenpyr-diethyl 30 + 50 20
    15 + 50 10
     8 + 50 10
  • TABLE A-5-7
    Post-emergence test/greenhouse
    Application rate Damage winter
    Active compound (+ safener) (g of a.i./ha) wheat (in %)
    I-17 30 70
    15 50
    8 40
    I-17 + mefenpyr-diethyl 30 + 50 40
    15 + 50 30
     8 + 50 20
  • TABLE A-5-8
    Post-emergence test/greenhouse
    Application rate Damage winter
    Active compound (+ safener) (g of a.i./ha) wheat (in %)
    I-14 1 40
    0.5 20
    I-14 + mefenpyr-diethyl   1 + 50 30
    0.5 + 50 10
  • TABLE A-5-9
    Post-emergence test/greenhouse
    Application rate Damage winter
    Active compound (+ safener) (g of a.i./ha) wheat (in %)
    I-18 2 50
    1 30
    I-18 + mefenpyr-diethyl 2 + 50 20
    1 + 50 10
  • TABLE A-5-10
    Post-emergence test/greenhouse
    Application rate Damage winter
    Active compound (+ safener) (g of a.i./ha) wheat (in %)
    I-15 30 70
    15 40
    8 30
    I-15 + mefenpyr-diethyl 30 + 50 10
    15 + 50 0
     8 + 50 0
  • TABLE A-5-11
    Post-emergence test/greenhouse
    Application rate Damage winter
    Safener (g of a.i./ha) barley (in %)
    mefenpyr-diethyl 50 0
  • TABLE A-5-12
    Post-emergence test/greenhouse
    Application rate Damage winter
    Active compound (+ safener) (g of a.i./ha) barley (in %)
    I-2 30 80
    15 70
    8 60
    I-2 + mefenpyr-diethyl 30 + 50 50
    15 + 50 20
     8 + 50 10
  • TABLE A-5-13
    Post-emergence test/greenhouse
    Application rate Damage winter
    Active compound (+ safener) (g of a.i./ha) barley (in %)
    I-17 30 80
    15 70
    8 70
    I-17 + mefenpyr-diethyl 30 + 50 70
    15 + 50 60
     8 + 50 20
  • TABLE A-5-14
    Post-emergence test/greenhouse
    Application rate Damage winter
    Active compound (+ safener) (g of a.i./ha) barley (in %)
    I-14 0.5 30
    0.25 10
    I-14 + mefenpyr-diethyl  0.5 + 50 20
    0.25 + 50 0
  • TABLE A-5-15
    Post-emergence test/greenhouse
    Application rate Damage winter
    Active compound (+ safener) (g of a.i./ha) barley (in %)
    I-18 2 60
    1 20
    0.5 10
    I-18 + mefenpyr-diethyl   2 + 50 20
      1 + 50 10
    0.5 + 50 0
  • TABLE A-5-19
    Post-emergence test/greenhouse
    Application rate Damage winter
    Active compound (+ safener) (g of a.i./ha) barley (in %)
    I-15 30 80
    15 70
    8 60
    I-15 + mefenpyr-diethyl 30 + 50 30
    15 + 50 20
     8 + 50 10

Claims (9)

1-9. (canceled)
10. A composition comprising an active compound combination comprising
(a) one or more compounds of formula (I)
Figure US20050009705A1-20050113-C00063
or salts thereof,
in which
Q1 represents O or S,
Q2 represents O or S,
R1 represents optionally cyano-, halogen-, or C1-C4-alkoxy-substituted alkyl having 1 to 6 carbon atoms; represents optionally cyano- or halogen-substituted alkenyl or alkynyl having in each case 2 to 6 carbon atoms; represents optionally cyano-, halogen-, or C1-C4-alkyl-substituted cycloalkyl or cycloalkylalkyl having in each case 3 to 6 carbon atoms in the cycloalkyl group and, where appropriate, 1 to 4 carbon atoms in any alkyl moiety; represents optionally nitro-, cyano-, halogen-, C1-C4-alkyl-, or C1-C4-alkoxy-substituted aryl or arylalkyl having in each case 6 or 10 carbon atoms in the aryl group and, where appropriate, 1 to 4 carbon atoms in any alkyl moiety; or represents optionally nitro-, cyano-, halogen-, C1-C4-alkyl-, or C1-C4-alkoxy-substituted heterocyclyl or heterocyclylalkyl having in each case up to 6 carbon atoms and additionally 1 to 4 nitrogen atoms and/or 1 or 2 oxygen or sulphur atoms in the heterocyclyl group and, where appropriate, 1 to 4 carbon atoms in any alkyl moiety,
R2 represents hydrogen, cyano, nitro, or halogen; represents optionally cyano-, halogen-, or C1-C4-alkoxy-substituted alkyl, alkoxy, alkoxycarbonyl, alkylthio, alkylsulphinyl, or alkylsulphonyl having in each case 1 to 6 carbon atoms in the alkyl group; or represents optionally cyano- or halogen-substituted alkenyl, alkynyl, alkenyloxy, or alkynyloxy having in each case 2 to 6 carbon atoms in the alkenyl or alkynyl group,
R3 represents hydrogen, hydroxyl, mercapto, amino, cyano, fluorine, chlorine, bromine, or iodine, represents optionally fluorine-, chlorine-, bromine-, cyano-, C1-C4-alkoxy-, C1-C4-alkyl-carbonyl-, or C1-C4-alkoxy-carbonyl-substituted alkyl having 1 to 6 carbon atoms; represents optionally fluorine-, chlorine-, and/or bromine- substituted alkenyl or alkynyl having in each case 2 to 6 carbon atoms; represents optionally fluorine-, chlorine-, cyano-, C1-C4-alkoxy-, or C1-C4-alkoxy-carbonyl-substituted alkoxy, alkylthio, alkylamino, or alkylcarbonylamino having in each case 1 to 6 carbon atoms in the alkyl group; represents alkenyloxy, alkynyloxy, alkenylthio, alkynylthio, alkenylamino, or alkynylamino having in each case 3 to 6 carbon atoms in the alkenyl or alkynyl group; represents dialkylamino having in each case 1 to 4 carbon atoms in the alkyl groups; represents optionally methyl- and/or ethyl-substituted aziridino, pyrrolidino, piperidino, or morpholino; represents optionally fluorine-, chlorine-, bromine-, cyano-, and/or C1-C4-alkyl-substituted cycloalkyl, cycloalkenyl, cycloalkyloxy, cycloalkylthio, cycloalkylamino, cycloalkylalkyl, cycloalkylalkoxy, cycloalkylalkylthio, or cycloalkylalkylamino having in each case 3 to 6 carbon atoms in the cycloalkyl or cycloalkenyl group and, where appropriate, 1 to 4 carbon atoms in any alkyl moiety; or represents optionally fluorine-, chlorine-, bromine-, cyano-, nitro-, C1-C4-alkyl-, trifluoromethyl-, C1-C4-alkoxy- and/or C1-C4-alkoxy-carbonyl-substituted aryl, arylalkyl, aryloxy, arylalkoxy, arylthio, arylalkylthio, arylamino, or arylalkylamino having in each case 6 or 10 carbon atoms in the aryl group and, where appropriate, 1 to 4 carbon atoms in any alkyl moiety,
R4 represents hydrogen, hydroxyl, amino, or cyano; represents C2-C10-alkylideneamino; represents optionally fluorine-, chlorine-, bromine-, cyano-, C1-C4-alkoxy-, C1-C4-alkyl-carbonyl-, or C1-C4-alkoxy-carbonyl-substituted alkyl having 1 to 6 carbon atoms; represents optionally fluorine-, chlorine-, and/or bromine-substituted alkenyl or alkynyl having in each case 2 to 6 carbon atoms; represents optionally fluorine-, chlorine-, bromine-, cyano-, C1-C4-alkoxy-, or C1-C4-alkoxy-carbonyl-substituted alkoxy, alkylamino, or alkyl-carbonylamino having in each case 1 to 6 carbon atoms in the alkyl group; represents alkenyloxy having 3 to 6 carbon atoms; represents dialkylamino having in each case 1 to 4 carbon atoms in the alkyl groups; represents optionally fluorine-, chlorine-, bromine-, cyano-, and/or C1-C4-alkyl-substituted cycloalkyl, cycloalkylamino, or cycloalkylalkyl having in each case 3 to 6 carbon atoms in the alkyl group and, where appropriate, 1 to 4 carbon atoms in any alkyl moiety; or represents optionally fluorine-, chlorine-, bromine-, cyano- nitro-, C1-C4-alkyl-, trifluoromethyl-, and/or C1-C4-alkoxy-substituted aryl or arylalkyl having in each case 6 or 10 carbon atoms in the aryl group and, where appropriate, 1 to 4 carbon atoms in any alkyl moiety, or
R3 and R4 together represent optionally branched alkanediyl having 3 to 6 carbon atoms, and
(b) at least one compound that improves crop plant compatibility selected from the group consisting of the compounds 4-dichloroacetyl-1-oxa-4-aza-spiro[4.5]-decane (AD-67, MON-4660), 1-dichloroacetyl-hexahydro-3,3,8a-trimethylpyrrolo[1,2-a]-pyrimidin-6(2H)-one (dicyclonon, BAS-145138), 4-dichloroacetyl-3,4-dihydro-3-methyl-2H-1,4-benzoxazine (benoxacor), 1-methyl-hexyl 5-chloro-quinolin-8-oxy-acetate (cloquintocet-mexyl), 3-(2-chloro-benzyl)-1-(1-methyl-1-phenyl-ethyl)-urea (cumyluron), α-(cyanomethoximino)-phenylacetonitrile (cyometrinil), 2,4-dichloro-phenoxyacetic acid (2,4-D), 4-(2,4-dichloro-phenoxy)-butyric acid (2,4-DB), 1-(1-methyl-1-phenyl-ethyl)-3-(4-methyl-phenyl)-urea (daimuron, dymron), 3,6-dichloro-2-methoxy-benzoic acid (dicamba), S-1-methyl-1-phenyl-ethyl piperidine-1-thiocarboxylate (dimepiperate), 2,2-dichloro-N-(2-oxo-2-(2-propenylamino)-ethyl)-N-(2-propenyl)-acetamide (DKA-24), 2,2-dichloro-N,N-di-2-propenyl-acetamide (dichlormid), 4,6-dichloro-2-phenyl-pyrimidine (fenclorim), ethyl 1-(2,4-dichloro-phenyl)-5-trichloro-methyl-1H-1,2,4-triazole-3-carboxylate (fenchlorazole-ethyl—cf. also related compounds in EP-A-174562 and EP-A-346620), phenyl-methyl 2-chloro-4-trifluoromethyl-thiazole-5-carboxylate (flurazole), 4-chloro-N-(1,3-dioxolan-2-yl-methoxy)-α-trifluoro-acetophenone oxime (fluxofenim), 3-dichloroacetyl-5-(2-furanyl)-2,2-dimethyl-oxazolidine (furilazole, MON-13900), ethyl-4,5-dihydro-5,5-diphenyl-3-isoxazolecarboxylate (isoxadifen-ethyl), 1-(ethoxycarbonyl)-ethyl 3,6-dichloro-2-methoxybenzoate (lactidichlor), (4-chloro-o-tolyloxy)-acetic acid (MCPA), 2-(4-chloro-o-tolyloxy)-propionic acid (mecoprop), diethyl 1-(2,4-dichlorophenyl)-4,5-dihydro-5-methyl-1H-pyrazole-3,5-dicarboxylate (mefenpyr-diethyl), 2-dichloromethyl-2-methyl-1,3-dioxolane (MG-191), 2-propenyl-1-oxa-4-azaspiro[4.5]decane 4-carbodithioate (MG-838), 1,8-naphthalic anhydride, α-(1,3-dioxolan-2-yl-methoximino)-phenylacetonitrile (oxabetrinil), 2,2-dichloro-N-(1,3-dioxolan-2-yl-methyl)-N-(2-propenyl)-acetamide (PPG-1292), 3-dichloroacetyl-2,2-dimethyl-oxazolidine (R-28725), 3-dichloroacetyl-2,2,5-trimethyl-oxazolidine (R-29148), 4-(4-chloro-o-tolyl)-butyric acid, 4-(4-chloro-phenoxy)-butyric acid, diphenylmethoxyacetic acid, methyl diphenylmethoxyacetate (MON-7400), ethyl diphenylmethoxyacetate, methyl 1-(2-chloro-phenyl)-5-phenyl-1H-pyrazole-3-carboxylate, ethyl 1-(2,4-dichloro-phenyl)-5-methyl-1H-pyrazole-3-carboxylate, ethyl 1-(2,4-dichloro-phenyl)-5-isopropyl-1H-pyrazole-3-carboxylate, ethyl 1-(2,4-dichloro-phenyl)-5-(1,1-dimethyl-ethyl)-1H-pyrazole-3-carboxylate, ethyl 1-(2,4-dichloro-phenyl)-5-phenyl-1H-pyrazole-3-carboxylate, ethyl 5-(2,4-dichloro-benzyl)-2-isoxazoline-3-carboxylate, ethyl 5-phenyl-2-isoxazoline-3-carboxylate, ethyl 5-(4-fluoro-phenyl)-5-phenyl-2-isoxazoline-3-carboxylate, 1,3-dimethyl-but-1-yl 5-chloro-quinolin-8-oxy-acetate, 4-allyloxy-butyl 5-chloro-quinolin-8-oxy-acetate, 1-allyloxy-prop-2-yl 5-chloro-quinolin-8-oxy-acetate, methyl 5-chloro-quinolin-8-oxy-acetate, ethyl 5-chloro-quinolin-8-oxy-acetate, allyl 5-chloro-quinolin-8-oxy-acetate, 2-oxo-prop-1-yl 5-chloro-quinolin-8-oxy-acetate, diethyl 5-chloro-quinolin-8-oxy-malonate, diallyl 5-chloro-quinolin-8-oxy-malonate, diethyl 5-chloro-quinolin-8-oxy-malonate, 4-carboxy-chroman-4-yl-acetic acid (AC-304415), 4-chloro-phenoxyacetic acid, 3,3′-dimethyl-4-methoxy-benzophenone, 1-bromo-4-chloromethylsulphonyl-benzene, 1-[4-(N-2-methoxy-benzoylsulphamoyl)-phenyl]-3-methyl-urea (alias N-(2-methoxy-benzoyl)-4-[(methylamino-carbonyl)-amino]-benzenesulphonamide), 1-[4-(N-2-methoxy-benzoylsulphamoyl)-phenyl]-3,3-dimethyl-urea, 1-[4-(N-4,5-dimethylbenzoyl-sulphamoyl)-phenyl]-3-methyl-urea, 1-[4-(N-naphthylsulphamoyl)-phenyl]-3,3-dimethyl-urea, N-(2-methoxy-5-methyl-benzoyl)-4-(cyclopropylamino-carbonyl)-benzenesulphonamide,
and
a compound of formula (IIa)
Figure US20050009705A1-20050113-C00064
where, for each of formulas (IIa), (IIb), or (IIc),
n represents a number between 0 and 5,
A1 represents one of the divalent heterocyclic groups
Figure US20050009705A1-20050113-C00065
A2 represents optionally C1-C4-alkyl- and/or C1-C4-alkoxy-carbonyl-substituted alkanediyl having 1 or 2 carbon atoms,
R5 represents hydroxyl, mercapto, amino, C1-C6-alkoxy, C1-C6-alkylthio, C1-C6-alkylamino, or di-(C1-C4-alkyl)-amino,
R6 represents hydroxyl, mercapto or amino; or optionally C1-C4-alkyl, C1-C4-alkoxy, or C2-C4-alkenoxy-substituted C1-C6-alkoxy, C2-C6-alkenoxy, C1-C6-alkylthio, C1-C6-alkylamino, or di-(C1-C4-alkyl)-amino,
R7 represents optionally fluorine-, chlorine-, and/or bromine-substituted C1-C4-alkyl,
R8 represents hydrogen; optionally fluorine-, chlorine-, and/or bromine-substituted C1-C6-alkyl, C2-C6-alkenyl, or C2-C6-alkynyl; C1-C4-alkoxy-C1-C4-alkyl, dioxolanyl-C1-C4-alkyl, furyl, furyl-C1-C4-alkyl, thienyl, thiazolyl, or piperidinyl; or optionally fluorine-, chlorine-, and/or bromine-, or C1-C4-alkyl-substituted phenyl,
R9 represents hydrogen; optionally fluorine-, chlorine-, and/or bromine-substituted C1-C6-alkyl, C2-C6-alkenyl, or C2-C6-alkynyl; C1-C4-alkoxy-C1-C4-alkyl, dioxolanyl-C1-C4-alkyl, furyl, furyl-C1-C4-alkyl, thienyl, thiazolyl, or piperidinyl, or optionally fluorine-, chlorine-, and/or bromine-, or C1-C4-alkyl-substituted phenyl; or R9 together with R8 represents C3-C6-alkanediyl or C2-C5-oxaalkanediyl, each of which is optionally substituted by C1-C4-alkyl, phenyl, furyl, a fused-on benzene ring, or by two substituents that together with the C atom to which they are attached form a 5- or 6-membered carbocycle,
R10 represents hydrogen, cyano, or halogen; or represents optionally fluorine, chlorine-, and/or bromine-substituted C1-C4-alkyl, C3-C6-cycloalkyl, or phenyl,
R11 represents hydrogen; or optionally hydroxyl-, cyano-, halogen-, or C1-C4-alkoxy-substituted C1-C6-alkyl, C3-C6-cycloalkyl, or tri-(C1-C4-alkyl)-silyl,
R12 represents hydrogen, cyano, or halogen; or represents optionally fluorine-, chlorine-, and/or bromine-substituted C1-C4-alkyl, C3-C6-cycloalkyl, or phenyl,
X1 represents nitro, cyano, halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, or C1-C4-haloalkoxy,
X2 represents hydrogen, cyano, nitro, halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, or C1-C4-haloalkoxy,
X3 represents hydrogen, cyano, nitro, halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, or C1-C4-haloalkoxy,
and
a compound of formula (IId)
Figure US20050009705A1-20050113-C00066
formula (IIe)
Figure US20050009705A1-20050113-C00067
where, for each of formulas (IId) or (IIe),
n represents a number between 0 and 5,
R13 represents hydrogen or C1-C4-alkyl,
R14 represents hydrogen or C1-C4-alkyl,
R15 represents hydrogen; optionally cyano-, halogen-, or C1-C4-alkoxy-substituted C1-C6-alkyl, C1-C6-alkoxy, C1-C6-alkylthio, C1-C6-alkylamino or di-(C1-C4-alkyl)-amino; or optionally cyano-, halogen-, or C1-C4-alkyl-substituted C3-C6-cycloalkyl, C3-C6-cycloalkyloxy, C3-C6-cycloalkylthio, or C3-C6-cycloalkylamino,
R16 represents hydrogen; optionally cyano-, hydroxyl-, halogen-, or C1-C4-alkoxy-substituted C1-C6-alkyl; optionally cyano- or halogen-substituted C3-C6-alkenyl or C3-C6-alkynyl; or optionally cyano-, halogen-, or C1-C4-alkyl-substituted C3-C6-cycloalkyl,
R17 represents hydrogen; optionally cyano-, hydroxyl-, halogen-, or C1-C4-alkoxy-substituted C1-C6-alkyl; optionally cyano- or halogen-substituted C3-C6-alkenyl or C3-C6-alkynyl; optionally cyano-, halogen-, or C1-C4-alkyl-substituted C3-C6-cycloalkyl; or optionally nitro-, cyano-, halogen-, C1-C4-alkyl-, C1-C4-halogenoalkyl-, C1-C4-alkoxy-, or C1-C4-halogenoalkoxy-substituted phenyl; or R17 together with R16 represents optionally C1-C4-alkyl-substituted C2-C6-alkanediyl or C2-C5-oxaalkanediyl,
X4 represents nitro, cyano, carboxyl, carbamoyl, formyl, sulphamoyl, hydroxyl, amino, halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, or C1-C4-haloalkoxy, and
X5 represents nitro, cyano, carboxyl, carbamoyl, formyl, sulphamoyl, hydroxyl, amino, halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, or C1-C4-haloalkoxy.
11. A composition according to claim 10 wherein
Q1 represents O or S,
Q2 represents O or S,
R1 represents optionally cyano-, fluorine-, chlorine-, methoxy-, or ethoxy-substituted methyl, ethyl, n- or i-propyl, or n-, i-, s-, or t-butyl; represents optionally cyano-, fluorine-, or chlorine-substituted propenyl, butenyl, propynyl, or butynyl; represents optionally cyano-, fluorine-, chlorine-, methyl-, or ethyl-substituted cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, or cyclohexylmethyl; represents optionally cyano-, fluorine-, chlorine-, bromine-, methyl-, ethyl-, n- or i-propyl-, trifluoromethyl-, methoxy-, ethoxy-, n- or i-propoxy-, difluoromethoxy-, or trifluoromethoxy-substituted phenyl, phenylmethyl, or phenylethyl; or represents optionally cyano-, fluorine-, chlorine-, bromine-, methyl-, ethyl-, n- or i-propyl-, methoxy-, ethoxy-, or n- or i-propoxy-substituted heterocyclyl or heterocyclyl-methyl, where each heterocyclyl group is selected from the group consisting of oxetanyl, thietanyl, furyl, tetrahydrofuryl, thienyl, and tetrahydrothienyl,
R2 represents hydrogen, cyano, fluorine, chlorine, or bromine; represents optionally cyano-, fluorine-, chlorine-, methoxy-, or ethoxy-substituted methyl, ethyl, n- or i-propyl, n-, i-, s-, or t-butyl, methoxy, ethoxy, n- or i-propoxy, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, methylthio, ethylthio, n- or i-propylthio, methylsulphinyl, ethylsulphinyl, methylsulphonyl, or ethylsulphonyl; or represents optionally cyano-, fluorine-, or chlorine-substituted propenyl, butenyl, propynyl, butynyl, propenyloxy, butenyloxy, propynyloxy, or butynyloxy,
R3 represents hydrogen, hydroxyl, mercapto, amino, cyano, fluorine, chlorine, or bromine; represents optionally fluorine-, chlorine-, cyano-, methoxy-, ethoxy-, n- or i-propoxy-, acetyl-, propionyl-, n- or i-butyroyl, methoxycarbonyl-, ethoxycarbonyl-, or n- or i-propoxycarbonyl-substituted methyl, ethyl, n- or i-propyl, or n-, i-, s-, or t-butyl; represents optionally fluorine-, chlorine-, and/or bromine-substituted ethenyl, propenyl, butenyl, ethynyl, propynyl, or butynyl; represents optionally fluorine-, chlorine-, cyano-, methoxy-, ethoxy-, n- or i-propoxy-, methoxycarbonyl-, ethoxycarbonyl-, or n- or i-propoxycarbonyl-substituted methoxy, ethoxy, n- or i-propoxy, n-, i-, s-, or t-butoxy, methylthio, ethylthio, n- or i-propylthio, n-, i-, s-, or t-butylthio, methylamino, ethylamino, n- or i-propylamino, n-, i-, s-, or t-butylamino, acetylamino, or propionylamino; represents propenyloxy, butenyloxy, ethynyloxy, propynyloxy, butynyloxy, propenylthio, butenylthio, propynylthio, butynylthio, propenylamino, butenylamino, propynylamino, or butynylamino; represents dimethylamino, diethylamino, or dipropylamino; represents optionally fluorine-, chlorine-, methyl-, and/or ethyl-substituted cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopentenyl, cyclohexenyl, cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy, cyclopropylthio, cyclobutylthio, cyclopentylthio, cyclohexylthio, cyclopropylamino, cyclobutylamino, cyclopentylamino, cyclohexylamino, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, cyclopropylmethoxy, cyclobutylmethoxy, cyclopentylmethoxy, cyclohexylmethoxy, cyclopropylmethylthio, cyclobutylmethylthio, cyclopentylmethylthio, cyclohexylmethylthio, cyclopropylmethylamino, cyclobutylmethylamino, cyclopentylmethylamino, or cyclohexylmethylamino; or represents optionally fluorine-, chlorine-, bromine-, methyl-, trifluoromethyl-, methoxy-, or methoxy-carbonyl-substituted phenyl, benzyl, phenoxy, benzyloxy, phenylthio, benzylthio, phenylamino, or benzylamino, and
R4 represents hydrogen, hydroxyl, or amino; represents optionally fluorine-, chlorine-, cyano-, methoxy-, or ethoxy-substituted methyl, ethyl, n- or i-propyl, or n-, i-, s-, or t-butyl; represents optionally fluorine, chlorine, and/or bromine-substituted ethenyl, propenyl, butenyl, propynyl, or butynyl; represents optionally fluorine-, chlorine-, cyano-, methoxy-, or ethoxy-substituted methoxy, ethoxy, n- or i-propoxy, n-, i-, s-, or t-butoxy, methylamino, ethylamino, n- or i-propylamino, or n-, i-, s-, or t-butylamino; represents propenyloxy or butenyloxy; represents dimethylamino or diethylamino; represents optionally fluorine-, chlorine-, methyl-, and/or ethyl-substituted cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylamino, cyclobutylamino, cyclopentylamino, cyclohexylamino, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, or cyclohexylmethyl; or represents optionally fluorine-, chlorine-, methyl-, trifluoromethyl-, and/or methoxy-substituted phenyl or benzyl, or
R3 and R4 together represent trimethylene (propane-1,3-diyl), tetramethylene (butane-1,4-diyl), or pentamethylene (pentane-1,5-diyl).
12. A composition according to claim 10 wherein
Q1 represents O,
Q2 represents O,
R1 represents optionally fluorine-, chlorine-, methoxy-, or ethoxy-substituted methyl, ethyl, or n- or i-propyl,
R2 represents fluorine, chlorine, or bromine; or represents optionally fluorine-, chlorine-, methoxy-, or ethoxy-substituted methyl, ethyl, or n- or i-propyl,
R3 represents hydrogen, chlorine, or bromine; represents optionally fluorine-, chlorine-, methoxy-, ethoxy-, or n- or i-propoxy-substituted methyl, ethyl, or n- or i-propyl; represents optionally fluorine- or chlorine-substituted ethenyl, propenyl, butenyl, propynyl, or butynyl; represents optionally fluorine-, chlorine-, methoxy-, ethoxy-, or n- or i-propoxy-substituted methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylamino, ethylamino, or n- or i-propylamino; represents propenyloxy, propynyloxy, propenylthio, propynylthio, propenylamino, or propynylamino; represents dimethylamino or diethylamino; represents optionally fluorine-, chlorine-, or methyl-substituted cyclopropyl, cyclopropyloxy, cyclopropylmethyl, or cyclopropylmethoxy, and
R4 represents optionally fluorine-, chlorine-, methoxy-, or ethoxy-substituted methyl, ethyl, or n- or i-propyl; represents optionally fluorine- or chlorine-substituted ethenyl, propenyl, or propynyl; represents optionally fluorine-, chlorine-, methoxy-, or ethoxy-substituted methoxy, ethoxy, or n- or i-propoxy; represents methylamino; or represents cyclopropyl.
13. A composition according to claim 10 wherein
n represents the numbers 0, 1, 2, 3, or 4,
A2 represents optionally methyl-, ethyl-, methoxycarbonyl-, or ethoxycarbonyl-substituted methylene or ethylene,
R5 represents hydroxyl, mercapto, amino, methoxy, ethoxy, n- or i-propoxy, n-, i-, s-, or t-butoxy, methylthio, ethylthio, n- or i-propylthio, n-, i-, s-, or t-butylthio, methylamino, ethylamino, n- or i-propylamino, n-, i-, s-, or t-butylamino, dimethylamino, or diethylamino,
R6 represents hydroxyl, mercapto, amino, methoxy, ethoxy, n- or i-propoxy, n-, i-, s-, or t-butoxy, methylthio, ethylthio, n- or i-propylthio, n-, i-, s-, or t-butylthio, methylamino, ethylamino, n- or i-propylamino, n-, i-, s-, or t-butylamino, dimethylamino, or diethylamino,
R7 represents optionally fluorine-, chlorine-, and/or bromine-substituted methyl, ethyl, or n- or i-propyl,
R8 represents hydrogen; optionally fluorine- and/or chlorine-substituted methyl, ethyl, n- or i-propyl, n-, i-, s-, or t-butyl, propenyl, butenyl, propynyl, butynyl, methoxymethyl, ethoxymethyl, methoxyethyl, ethoxyethyl, dioxolanylmethyl, furyl, furylmethyl, thienyl, thiazolyl, piperidinyl; or optionally fluorine-, chlorine-, methyl-, ethyl-, n- or i-propyl-, or n-, i-, s-, or t-butyl-substituted phenyl,
R9 represents hydrogen; optionally fluorine- and/or chlorine-substituted methyl, ethyl, n- or i-propyl, n-, i-, s-, or t-butyl, propenyl, butenyl, propynyl, butynyl, methoxymethyl, ethoxymethyl, methoxyethyl, ethoxyethyl, dioxolanylmethyl, furyl, furylmethyl, thienyl, thiazolyl, piperidinyl; or optionally fluorine-, chlorine-, methyl-, ethyl-, n- or i-propyl-, or n-, i-, s-, or t-butyl-substituted phenyl; or R9 together with R8 represents one of the radicals —CH2—O—CH2-CH2— or —CH2-CH2—O—CH2-CH2—, which are optionally substituted by methyl, ethyl, furyl, phenyl, a fused benzene ring, or by two substituents that together with the C atom to which they are attached form a 5- or 6-membered carbocycle,
R10 represents hydrogen, cyano, fluorine, chlorine, or bromine; or represents optionally fluorine-, chlorine-, and/or bromine-substituted methyl, ethyl, n- or i-propyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, or phenyl,
R11 represents hydrogen; or optionally hydroxyl-, cyano-, fluorine-, chlorine, methoxy-, ethoxy-, or n- or i-propoxy-substituted methyl, ethyl, n- or i-propyl, or n-, i-, s-, or t-butyl,
R12 represents hydrogen, cyano, fluorine, chlorine, or bromine; or represents optionally fluorine-, chlorine-, and/or bromine-substituted methyl, ethyl, n- or i-propyl, n-, i-, s-, or t-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, or phenyl,
X1 represents nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s-, or t-butyl, difluoromethyl, dichloromethyl, trifluoromethyl, trichloromethyl, chlorodifluoromethyl, fluorodichloromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy, or trifluoromethoxy,
X2 represents hydrogen, nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s-, or t-butyl, difluoromethyl, dichloromethyl, trifluoromethyl, trichloromethyl, chlorodifluoromethyl, fluorodichloromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy, or trifluoromethoxy,
X3 represents hydrogen, nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s-, or t-butyl, difluoromethyl, dichloromethyl, trifluoromethyl, trichloromethyl, chlorodifluoromethyl, fluorodichloromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy, or trifluoromethoxy,
R13 represents hydrogen, methyl, ethyl, or n- or i-propyl,
R14 represents hydrogen, methyl, ethyl, or n- or i-propyl,
R15 represents hydrogen; optionally cyano-, fluorine-, chlorine-, methoxy- ethoxy-, or n- or i-propoxy-substituted methyl, ethyl, n- or i-propyl, n-, i-, s-, or t-butyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s-, or t-butoxy, methylthio, ethylthio, n- or i-propylthio, n-, i-, s-, or t-butylthio, methylamino, ethylamino, n- or i-propylamino, n-, i-, s-, or t-butylamino, dimethylamino, or diethylamino; or optionally cyano-, fluorine-, chlorine-, bromine-, methyl-, ethyl-, or n- or i-propyl-substituted cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy, cyclopropylthio, cyclobutylthio, cyclopentylthio, cyclohexylthio, cyclopropylamino, cyclobutylamino, cyclopentylamino, or cyclohexylamino,
R16 represents hydrogen; optionally cyano-, hydroxyl-, fluorine- chlorine-, methoxy-, ethoxy-, or n- or i-propoxy-substituted methyl, ethyl, n- or i-propyl, or n-, i-, or s-butyl; optionally cyano-, fluorine-, chlorine-, or bromine-substituted propenyl, butenyl, propynyl, or butynyl; or optionally cyano-, fluorine-, chlorine-, bromine-, methyl- ethyl-, n- or i-propyl-substituted cyclopropyl, cyclobutyl, cyclopentyl, or cyclohexyl,
R17 represents hydrogen; optionally cyano-, hydroxyl-, fluorine- chlorine-, methoxy-, ethoxy-, or n- or i-propoxy-substituted methyl, ethyl, n- or i-propyl, or n-, i-, or s-butyl; optionally cyano-, fluorine-, chlorine-, or bromine-substituted propenyl, butenyl, propynyl, or butynyl; or optionally cyano-, fluorine-, chlorine-, bromine-, methyl- ethyl-, or n- or i-propyl-substituted cyclopropyl, cyclobutyl, cyclopentyl, or cyclohexyl; or optionally nitro-, cyano-, 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; or R17 together with R16 represents in each case optionally methyl- or ethyl-substituted butane-1,4-diyl (trimethylene), pentane-1,5-diyl, 1-oxabutane-1,4-diyl, or 3-oxapentane-1,5-diyl,
X4 represents nitro, cyano, carboxyl, carbamoyl, formyl, sulphamoyl, hydroxyl, amino, 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, and
X5 represents nitro, cyano, carboxyl, carbamoyl, formyl, sulphamoyl, hydroxyl, amino, 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.
14. A composition according to claim 10 wherein the crop-plant-compatibility-improving compound is one or more compounds selected from the group consisting of the active compounds AD-67, cloquintocet-mexyl, dichlormid, fenchlorazole-ethyl, isoxadifen-ethyl, mefenpyr-diethyl, MON-7400, flurazole, furilazole, fenchlorim, cumyluron, dymron, a compound of formula (IId)
Figure US20050009705A1-20050113-C00068
in which R13 and R14 each represent hydrogen, R15 represents methoxymethyl, (X4)n represents 2-methoxy, and (X5)n represents hydrogen, and
a compound of formula (IIe)
Figure US20050009705A1-20050113-C00069
in which R13 and R16 each represent hydrogen, R17 represents cyclopropyl, (X4)n represents the group 2-methoxy or the two groups 2-methoxy and 5-methyl, and (X5)n represents hydrogen.
15. A composition according to claim 10 comprising an active compound combination comprising
(a) a compound of formula (I)
Figure US20050009705A1-20050113-C00070
or a salt thereof,
in which Q1 and Q2 each represent oxygen, R1, R2, and R4 each represent methyl, and R3 represents methoxy, and
(b) a crop-plant-compatibility-improving compound of formula (IIe)
Figure US20050009705A1-20050113-C00071
in which R13 and R16 each represent hydrogen, R17 represents cyclopropyl, (X4)n represents 2-methoxy, and (X5)n represents hydrogen.
16. A method for controlling undesirable plants comprising allowing an effective amount of a composition according to claim 10 to act on undesirable plants and/or their habitat.
17. A process for preparing a herbicidal composition comprising mixing a composition according to claim 10 with one or more surfactants and/or extenders.
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