EP2323483A2 - Association herbicide-phytoprotecteur composée d'anilides de difluorométhanesulfonyle à substitution diméthoxytriazinyle - Google Patents

Association herbicide-phytoprotecteur composée d'anilides de difluorométhanesulfonyle à substitution diméthoxytriazinyle

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Publication number
EP2323483A2
EP2323483A2 EP09777755A EP09777755A EP2323483A2 EP 2323483 A2 EP2323483 A2 EP 2323483A2 EP 09777755 A EP09777755 A EP 09777755A EP 09777755 A EP09777755 A EP 09777755A EP 2323483 A2 EP2323483 A2 EP 2323483A2
Authority
EP
European Patent Office
Prior art keywords
herbicide
methyl
safener
crops
compounds
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP09777755A
Other languages
German (de)
English (en)
Inventor
Erwin Hacker
Christopher Hugh Rosinger
Chieko Ueno
Georg Bonfig-Picard
Frank Ziemer
Shinichi Shirakura
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Bayer CropScience AG
Original Assignee
Bayer CropScience AG
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Filing date
Publication date
Application filed by Bayer CropScience AG filed Critical Bayer CropScience AG
Publication of EP2323483A2 publication Critical patent/EP2323483A2/fr
Withdrawn legal-status Critical Current

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Classifications

    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • 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
    • A01N43/66—1,3,5-Triazines, not hydrogenated and not substituted at the ring nitrogen atoms
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
    • 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
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/80—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2

Definitions

  • the present invention relates to the technical field of crop protection agents, in particular herbicide-safener combinations, which are outstandingly suitable for use against harmful plants in crops, and which for example (eg) in the Vorsaatvon (with or without incorporation), in the pre-emergence or postemergence in sown and / or planted crops such as in wheat (hard and soft wheat), corn, soybean, sugarbeet, sugarcane, cotton, rice (planted or sown under 'upland' or 'paddy' conditions with indica and / or Japonica species as well as hybrids / mutants / GMOs), beans (such as bush bean and horse bean), flax, barley, oats, rye, triticale, rapeseed, potato, millet (sorghum), pasture grass, green / lawns, in orchards (plantation crops ) or on non-cultivated areas (eg squares of residential and industrial plants, railway tracks).
  • sequence applications are also possible.
  • It relates to a combination containing at least one herbicide from the group of ⁇ / - ⁇ 2- [4,6-dimethoxy- (1, 3,5) -triazine-2 (-carbonyl or -hydroxy-methyl)] - 6-halo - phenylj-difluoromethanesulfonamides or their ⁇ / -methyl derivatives and / or salts thereof, hereinafter also referred to as "dimethoxytriazinyl-substituted
  • Difluoromethanesulfonylanilide ", and at least one active ingredient from the group of safeners.
  • cyclic-substituted sulfonamides have herbicidal properties (eg WO 93/09099 A2, WO 96/41799 A1). These include the phenyldifluoromethanesulfonamides, which are also referred to as Difluormethansulfonylanilide.
  • the latter are, for example, phenyl derivatives which are monosubstituted or polysubstituted, inter alia with Dimethoxypyimidinyl (eg WO 00/006553 A1) or dimethoxytriazinyl and a further halogen substitution (eg WO 2005/096818 A1, WO 2007/031208 A2).
  • the herbicidal activity of the dimethoxytriazinyl-substituted difluoromethanesulfonylanilides against harmful plants is at a high level and generally depends on the application rate, the particular preparation form, the particular harmful plants to be controlled or the harmful plant spectrum, climatic and soil conditions, etc. Other criteria in this context are the duration of action or rate of degradation of the herbicide, the general rate of action (faster efficacy), the spectrum of activity and behavior towards secondary crops (replication problems) or the general application flexibility (control of weeds in their various stages of growth).
  • herbicidal active ingredients are sometimes not fully compatible with some important crops, such as in wheat (hard and soft wheat), corn, soy, sugar beet, sugar cane, cotton, rice (planted or sown under 'Upland 1 - or' Paddy ' Conditions with Indica and / or Japonica species as well as hybrids / mutants / GMOs), beans (such as bush bean and horse bean), flax, barley, oats, rye, triticale, rapeseed, potato, millet (sorghum), pasture grass, green - / Lawns or in orchards (plantation crops). Therefore, they can not be used in some cultures to ensure the desired broad herbicidal activity against harmful plants, in addition to the single application also Sequence applications are included.
  • herbicide-safener combinations ie the mixture of herbicides and safeners and other components from the group of other agrochemical active ingredients and / or plant protection conventional additives and formulation auxiliaries, which to the desired Crop compatibility.
  • the combined use of several drugs often causes phenomena of chemical, physical or biological incompatibility, e.g. lack of stability of a common formulation, decomposition of an active substance or antagonism in the biological activity of the active ingredients. Therefore, potentially suitable combinations have to be selected and tested experimentally for their suitability, whereby negative as well as positive results can not be ruled out in advance.
  • the object of the present invention was to find in the prior art herbicidal agents in which the compatibility of the above-mentioned herbicides against important crops is increased and thus the selective use is ensured.
  • herbicide-safener combinations of dimethoxytriazinyl-substituted Difluoromethanesulfonylanilides in combination with compounds (active ingredients) can be solved from the group of safeners, which cooperate in a particularly favorable manner, for example when they are used to control undesirable plant growth in crops such as wheat (hard and soft wheat), corn, soybean, sugar beet, sugarcane , Cotton, rice (planted or sown under 'Upland 1 ' or 'Paddy' conditions with Indica and / or Japonica species and hybrids / mutants / GMOs), beans (such as bushbeam and horse bean), flax, barley, oats , Rye, triticale, rapeseed, potato, millet (sorghum), pasture, green / lawns or in orchards (plantation crops), especially in rice crops (planted or sown under 'Upland 1 ' or 'P
  • the present invention thus provides a herbicide-safener combination comprising components (A) and (B), wherein
  • R 1 is halogen, preferably fluorine or chlorine
  • R 2 is hydrogen and R 3 is hydroxyl or
  • R 4 is hydrogen or methyl
  • (B) means one or more compounds from the group of safeners.
  • herbicide-safener combinations of the invention may contain additional additional components: e.g. agrochemical active compounds of another type and / or customary in plant protection additives and / or formulation auxiliaries, or used together with these.
  • additional additional components e.g. agrochemical active compounds of another type and / or customary in plant protection additives and / or formulation auxiliaries, or used together with these.
  • the use of the term "herbicide-safener combination (s)” or “combination (s)” also includes the “herbicidal agents" thus produced.
  • component (s) or “individual component (s)
  • the terms “herbicide (s)”, “safener”, “single herbicide (s)”, “compound (s)” or “active substance (e) used synonymously in context.
  • the compounds of formula (I) can form salts. Salt formation can be effected by the action of a base on those compounds of the formula (I) which carry an acidic hydrogen atom.
  • suitable bases are organic amines, such as trialkylamines, morpholine, piperidine or pyridine, and ammonium, alkali metal or alkaline earth metal hydroxides, carbonates and bicarbonates, in particular sodium and potassium hydroxide, sodium and potassium carbonate and
  • Sodium and potassium bicarbonate, alkali metal or alkaline earth metal especially sodium or potassium, ethyl, n-propyl, i-propylate, n-butoxide or t-butylate.
  • These salts are compounds in which the acidic hydrogen is replaced by an agriculturally suitable cation, for example metal salts, in particular alkali metal salts or alkaline earth metal salts, in particular sodium and potassium salts, or else ammonium salts, salts with organic amines or quaternary ammonium salts Examples of cations of the formula [NRR ' R ' R '' ] + , where R 1 to R '' each independently of one another are an organic radical, in particular alkyl, aryl, arylalkyl or alkylaryl.
  • the compounds of the formula (I) can also be prepared by addition of a suitable inorganic or organic acid, such as for example, mineral acids such as HCl, HBr, H 2 SO 4 , H 3 PO 4 or HNO 3 , or organic acids, for example carboxylic acids such as formic acid, acetic acid, propionic acid, oxalic acid, lactic acid or salicylic acid or sulfonic acids such as p-toluenesulfonic acid , to form a basic group such as amino, alkylamino, dialkylamino, piperidino, morpholino or pyridino, salts. These salts then contain the conjugate base of the acid as an anion.
  • mineral acids such as HCl, HBr, H 2 SO 4 , H 3 PO 4 or HNO 3
  • organic acids for example carboxylic acids such as formic acid, acetic acid, propionic acid, oxalic acid, lactic acid or salicylic acid or sul
  • component (A) are the following compounds (A-1) to (A-8) of the formulas (A1), (A2), (A3), (A4), (A5), (A6), (A7) and (A8) or salts thereof:
  • component (A) particularly preferred are the compounds (A-1), (A-2) and (A-3).
  • Said formula (I) comprises all stereoisomers and mixtures thereof, in particular racemic mixtures, and - as far as enantiomers are possible - the respective biologically active enantiomers. This also applies to possible rotamers of the formula (I).
  • the herbicides of group (A) predominantly inhibit the enzyme acetolactate synthase (ALS) and thus protein biosynthesis in plants.
  • the application rates are generally in the range of 0.1 g to 500 g AS / ha, preferably 0.5 g to 200 g AS / ha, more preferably 1, 0 g to 150 g AS / ha.
  • the safeners contained as component (B) are compounds which are suitable for reducing phytotoxic effects of crop protection active ingredients such as herbicides on crop plants.
  • herbicides (A) already have good to sufficient selectivity in many cultures, phytotoxicities on the crop plants can in principle occur in some crops and, above all, in the case of mixtures with other herbicides which are less selective.
  • safeners are of particular interest, which can be used alone or together with other safeners in an antidote effective content to the phytotoxic side effects of the herbicides / pesticides used z.
  • the radicals may be alkyl, alkoxy, haloalkyl, haloalkoxy, alkylamino, alkylthio, haloalkylthio, alkylsulfinyl, alkylsulfonyl, haloalkylsulfinyl and haloalkylsulfonyl, and the corresponding unsaturated and / or substituted radicals in each case be straight-chain or branched in the carbon skeleton.
  • these radicals are the lower carbon skeletons, e.g.
  • Alkyl radicals also in the composite meanings such as alkoxy, haloalkyl, etc., mean e.g.
  • Alkenyl and alkynyl radicals have the meaning of the possible unsaturated radicals corresponding to the alkyl radicals; wherein at least one double bond or triple bond, preferably a double bond or triple bond is included.
  • Alkenyl means e.g.
  • Alkynyl means e.g. Ethynyl, propargyl, but-2-yn-1-yl, but-3-yn-1-yl, 1-methyl-but-3-yn-1-yl.
  • Halogen is fluorine, chlorine, bromine or iodine.
  • Haloalkoxy is, for example, OCF 3 , OCHF 2 , OCH 2 F, CF 3 CF 2 O, OCH 2 CF 3 and OCH 2 CH 2 Cl; the same applies to haloalkenyl and other halogen-substituted radicals.
  • Aryl means a mono-, bi- or polycyclic aromatic system, for example phenyl or naphthyl, preferably phenyl.
  • a heterocyclic radical or ring may be saturated, unsaturated or heteroaromatic; unless otherwise defined, it preferably contains one or more, in particular 1, 2 or 3 heteroatoms in the heterocyclic ring, preferably from the group N, O and S; it is preferably an aliphatic heterocyclyl radical having 3 to 7 ring atoms or a heteroaromatic radical having 5 or 6 ring atoms.
  • the heterocyclic radical may be, for example, a heteroaromatic radical or ring (heteroaryl), such as a mono-, bi- or polycyclic aromatic system in which at least one ring contains one or more heteroatoms.
  • a heteroaromatic radical or ring such as a mono-, bi- or polycyclic aromatic system in which at least one ring contains one or more heteroatoms.
  • it is a heteroaromatic ring having a heteroatom from the group N, O and S, for example pyridyl, pyrrolyl,
  • Thienyl or furyl is preferably a corresponding heteroaromatic ring with 2 or 3 heteroatoms, z.
  • it is a partially or fully hydrogenated heterocyclic radical having 2 heteroatoms from the group N, O and S, for example piperazinyl, dioxanyl, dioxolanyl, oxazolinyl, isoxazolinyl, oxazolidinyl, isoxazolidinyl and morpholinyl.
  • alkyl, alkoxy or haloalkoxy radicals are optionally cyclically linked to one another, provided that they are" o / t ⁇ o-continuous ", for example the groups benzo 1, 4-dioxan-yl, 1,3-benzodfoxol-yl, chroman-yl, 3,4-dihydro-1H-chroman-yl, 2,3-dihydro-i-benzofuran, 1,3-dihydroxy 1-benzofuran-yl, indan-yl, 1, 2,3,4-tetrahydronaphthyl, and their halogenated to the saturated carbon moieties, in particular fluorinated analogues.
  • substituted by one or more radicals means one or more identical or different radicals.
  • first substituent level if they contain hydrocarbon-containing moieties, may optionally be further substituted there (“second substituent plane"), for example by one of the substituents as defined for the first substituent level.
  • second substituent plane corresponds further substituent levels.
  • substituted radical includes only one or two substituent levels.
  • radicals with C atoms those having 1 to 6 C atoms, preferably 1 to 4 C atoms, in particular 1 or 2 C atoms, are preferred.
  • preferred substituents are selected from the group halogen, for example fluorine and chlorine, (CrC 4) alkyl, preferably methyl or ethyl, (C- ⁇ -C 4) -haloalkyl, preferably trifluoromethyl, (C 1 -C 4 -alkoxy J , preferably methoxy or ethoxy, (C 1 -C 4 ) -haloalkoxy, nitro and cyano.
  • halogen for example fluorine and chlorine
  • Optionally substituted phenyl is preferably phenyl which is unsubstituted or substituted one or more times, preferably up to trisubstituted, by identical or different radicals from the group halogen, (Ci-C 4) alkyl, (CrC 4) alkoxy, (CrC 4) - haloalkyl , (CrC 4 ) haloalkoxy and nitro, for example o-, m- and p-ToIyI, demethylphenyls, 2-, 3- and 4-chlorophenyl, 2-, 3- and 4-trifluoromethyl and 2-, 3 - And 4-trihalomethyl-phenyl, 2,4-, 3,5-, 2,5- and 2,3-dichlorophenyl, o-, m- and p-methoxyphenyl
  • n A is a natural number from O to 5, preferably O to 3;
  • RA 1 is halogen, (C r C 4 ) alkyl, (C 1 -C 4 ) alkoxy, nitro or (C 1 -C 4 ) haloalkyl;
  • W A is an unsubstituted or substituted divalent heterocyclic radical selected from the group consisting of the pentally unsaturated or aromatic five-membered heterocycles having 1 to 3 hetero ring atoms from the group consisting of N and O, where at least one
  • N atom and at most one O atom is contained in the ring, preferably a radical from the group (W A 1 ) to (W A 4 ),
  • R A 3 is hydrogen or an unsubstituted or substituted aliphatic hydrocarbon radical, preferably having a total of 1 to 18 C atoms;
  • RA 4 is hydrogen, (C 1 -C 6 ) alkyl, (C 1 -C 6 ) alkoxy or substituted or unsubstituted phenyl;
  • R A 5 is H, (Ci-C 8 ) AllCyI, (CrC 8 ) haloalkyl, (Ci-C 4 ) alkoxy (Ci-C 8 ) alkyl, cyano or
  • R A 9 is hydrogen, (Ci-C 8 ) alkyl, (C r C 8 ) haloalkyl, (C 1 - C 4 ) alkoxy- (C 1 -C 4 ) alkyl, (C r C 6 ) hydroxyalkyl ((C3-Ci2) cycloalkyl, or Tn C 1 -
  • RA 6, R 7 A, RA 8 are identical or different hydrogen, (CrC 8) alkyl, (CrC 8) halo- alkyl, (C 3 -C 2) cycloalkyl or substituted or unsubstituted phenyl;
  • RB 1 is halogen, (C r C 4 ) alkyl, (C 1 -C 4 ) alkoxy, nitro or (C r C 4 ) haloalkyl;
  • n B is a natural number from 0 to 5, preferably 0 to 3;
  • RB 2 is ORB 3 , SR 8 3 or NR B 3 R B 4 or a saturated or unsaturated 3- to 7-membered heterocycle having at least one N atom and up to 3 heteroatoms, preferably from the group O and S, which is connected via the N-atom to the carbonyl group in (S2) and is unsubstituted or substituted by radicals from the group (-C 4) -alkyl, (Ci-C 4) -alkoxy or optionally substituted phenyl, preferably a radical of the formula ORB 3 , NHR 8 4 or N (CH 3 ) 2 , in particular of the formula ORB 3 ;
  • RB 3 is halogen, (C
  • RB 4 is hydrogen, (Ci-C 6 ) alkyl, (C r C 6 ) alkoxy or substituted or unsubstituted phenyl;
  • TB is a (Ci or C 2 ) alkanediyl chain which is unsubstituted or substituted by one or two (CrC 4 ) alkyl radicals or by [(CrC 3 ) alkoxy] carbonyl;
  • Rc 3 are identical or different hydrogen, (CrC 4) alkyl, (C2-C4) alkenyl, (C 2 -C 4) AI kinyl, (CrC 4) haloalkyl, (C 2 -C 4) haloalkenyl, (C r C 4 ) alkylcarbamoyl
  • R-29148 (3-dichloroacetyl-2,2,5-trimethyl-1,3-oxazolidine) from Stauffer (S3-2),
  • R-28725" (3-dichloroacetyl-2,2, -dimethyl-1,3-oxazolidine) from Stauffer (S3-3),
  • TI-35 (1-dichloroacetyl-azepane) from TRI-Chemical RT (S3-8),
  • X 0 is CH or N
  • RD 1 is CO-NRD 5 RD 6 or NHCO-R D 7 ;
  • RD 2 is halogen, (dC 4) haloalkyl, (C 1 -C 4) HaIOaIkOXy, nitro, (C r C4) alkyl, (C 1 -C 4) -alkoxy, (C r C 4) alkylsulfonyl, (C r C 4 ) alkoxycarbonyl or
  • RD 5 is hydrogen, (C r C 6 ) alkyl, (C 3 -C 6 ) cycloalkyl, (C 2 -C 6 ) alkenyl, (C 2 -C 6 ) alkynyl, (C 5 -C 6 ) cycloalkenyl, phenyl or 3- to 6-membered heterocyclyl containing VD heteroatoms from the group nitrogen, oxygen and sulfur, wherein the seven latter radicals by v D substituents from the group
  • Halogen (C 1 -C 6) -alkoxy, (C r C 6) haloalkoxy, (C 1 -C 2) AI kylsu If ynyl, (C 1 - C 2) alkylsulfonyl, (C 3 -C 6) cycloalkyl, ( d ⁇ alkoxycarbonyl, (C 1 - C 4) alkylcarbonyl and phenyl and, in the case of cyclic radicals, also (C 1 -C 4) alkyl and (CrC 4 ) haloalkyl are substituted;
  • R D 6 is hydrogen, (C 1 -C 6 ) alkyl, (C 2 -C 6 ) alkenyl or (C 2 -C 6 ) alkynyl, where the three last-mentioned radicals are represented by v D radicals from the group halogen, hydroxy, (C 1 -C 4 ) 4 ) alkyl, (CrC 4 ) alkoxy and (Ci-C 4 ) alkylthio are substituted, or RD 5 and R 0 6 together with the nitrogen atom carrying a
  • RD 7 is hydrogen, (C r C4) alkylamino, di- (C r C 4) alkylamino, (C r C6) alkyl,
  • RD 4 is halogen, (C r C 4 ) alkyl, (C r C 4 ) alkoxy, CF 3; m D 1 or 2;
  • VD is 0, 1, 2 or 3;
  • Acylsulfamoylbenzoeklareamide for example, the following formula (S4 b ), for example, are known from WO-A-99/16744, eg those in which
  • N-acylsulfamoylphenylurea type compounds of formula (S4) e.g. are known from EP-A-365484,
  • R 0 8 and RD 9 independently of one another are hydrogen, (C 1 -C 8 ) -alkyl, (C 3 -C 8 ) -cycloalkyl, (C 3 -C 6 ) -alkenyl, (C 3 -C 6 ) -alkynyl,
  • RD 4 is halogen, (C r C 4 ) alkyl, (Ci-C 4 ) alkoxy, CF 3 rriD 1 or 2;
  • S6 active compounds from the class of 1, 2-dihydroquinoxaline-2-ones (S6), e.g.
  • a E is COORE 3 or COSR E 4
  • RE 3 , RE 4 are each independently hydrogen, (Ci-C 4 ) alkyl, (C 2 -
  • n E 1 is 0 or 1 riE 2 , n E 3 independently 0, 1 or 2, preferably:
  • Methyl diphenylmethoxyacetate (CAS No. 41858-19-9) (S7-1).
  • X F is CH or N
  • R F 1 when X is F CH halogen, (C 1 -C 4) AIRyI, (C r C 4) haloalkyl, (Ci -C 4) AI koxy, (C r C4) haloalkoxy,
  • RF 2 is hydrogen or (C r C 4 ) alkyl
  • R F 3 is hydrogen, (Ci-C 8 ) alkyl, (C 2 -C 4 ) alkenyl, (C 2 -C 4 ) alkynyl, or aryl, wherein each of the aforementioned C containing radicals unsubstituted or substituted by one or more, preferably up to three identical or different radicals selected from the group consisting of halogen and alkoxy; mean, or their salts,
  • R F 3 is hydrogen, (C r C 8 ) alkyl, (C 2 -C 4 ) alkenyl, (C 2 -C 4 ) alkynyl, or aryl, wherein each of the aforementioned C-containing radicals is unsubstituted or substituted by one or more, preferably up to three identical or different radicals from the group consisting of halogen and alkoxy substituted, mean, or their salts.
  • S9 Agents from the class of 3- (5-tetrazolylcarbonyl) -2-quinolones (S9), e.g. 1, 2-Dihydro-4-hydroxy-1-ethyl-3- (5-tetrazolylcarbonyl) -2-quinolone (CAS Reg. No. 219479-18-2), 1, 2-dihydro-4-hydroxy-1 -methyl-3- (5-tetrazolylcarbonyl) -2-quinolone (CAS Reg. No. 95855-00-8) (S9-1) as described in WO-A-1999/000020.
  • RG 2 (C r Ci 6) alkyl, (C 2 -C 6) AI keny I, (C 3 -C 6) cycloalkyl, aryl; Benzyl, halobenzyl, RG 3 is hydrogen or (C r C 6 ) alkyl.
  • Oxabetrinil ((Z) -1, 3-dioxolan-2-ylmethoxyimino (phenyl) acetonitrile) (S11-1), which is known as a seed dressing safener for millet against damage by metolachlor,
  • Fluorofenim (1- (4-chlorophenyl) -2,2,2-trifluoro-1-ethanone-O- (1,3-dioxolan-2-ylmethyl) -oxime) (S11-2) which was used as seed dressing Safener for millet is known against damage from metolachlor, and
  • Cyometrinil or “CGA-43089” ((Z) -cyanomethoxyimino (phenyl) acetonitrile) (S11-3), which is known as a seed dressing safener for millet against damage by metolachlor.
  • Isothiochromanone (S12) class agents e.g. Methyl - [(3-oxo-1H-2-benzothiopyran-4 (3H) -ylidene) methoxy] acetate (CAS No. 205121-04-6) (S12-1) and related compounds of WO-A -1998 / 13361.
  • Naphthalene anhydride (1,8-naphthalenedicarboxylic anhydride) (S13-1), which is known as
  • Seed pickling safener for maize known for damage from thiocarbamate herbicides
  • Pretilachlor is known in sown rice
  • Imidazolinone is known, "MG-191" (CAS Reg. No. 96420-72-3) (2-dichloromethyl-2-methyl-1,3-dioxolane)
  • component (B) preferred compounds are, including possible stereoisomers and the commonly used in agriculture esters or salts: (S1-1) mefenpyr (-diethyl), (S1-7) fenchlorazoles (-ethyl), (S1-12) isoxadifen (-ethyl), (S2-1) cloquintocet (-mexyl), (S3-1) dichloromid, (S3-2) R-29148 (3-dichloroacetyl-2,2 > 5-trimethyl-1,3-oxazolidine) > (S3-3) R-28725 (3-dichloroacetyl-2,2, -dimethyl-1,3-oxazolidine), (S3-4) benoxacor, (S3-5) PPG-1292 (N-allyl-N-) [(1,3-dioxolan-2-yl) -methyl] -dichloroacetamide), (S3-6) DKA-24 (N-allyl-N - [
  • Cyprosulfamides (S11-1) oxabetrinil, (S11-2) Fluxofenim, (S11-3) Cyometrinil, (S13-1) Naphthalic anhydrides, (S13-2) Fenclorim, (S13-3) Flurazoles; most notably preferably (S1-1) mefenpyr (-diethyl), (S1-7) fenchlorazole (-ethyl), (S1-12) isoxadifen (-ethyl), (S2-1) cloquintocet (-mexyl), (S3-1) Dichloromide, (S3-4) benoxacor, (S3-7) AD-67 / MON 4660 (3-dichloroacetyl-1-oxa-3-aza-spiro [4,5] decane), (S3-10) / (S3 -11) furilazoles, (S4-1) cyprosulfamides, (S11-2) flux
  • herbicides (A) and safeners (B) are those in which the safener (B) is selected from the group of safeners consisting of the compounds (S1-1) mefenpyr (-diethyl), (S1-12) Isoxadifen (-ethyl), (S2-1) Cloquintocet (-mexyl), (S4-1) Cyprosulfamide, most preferred as safener (B) are (S1-1) mefenpyr (-diethyl), (S1-12) isoxadifen (-ethyl), and (S4-1) cyprosulfamides.
  • the safeners (compounds of group B) of the formulas (S-1) to (S-13) are suitable for the reduction of phytotoxic effects that can occur when using herbicides (A) in crops, without the effectiveness of these herbicidal active ingredients against harmful plants essential to impair.
  • the field of application of conventional crop protection agents can be considerably extended, e.g. on crops in which the use of herbicides was previously not possible or only possible to a limited extent.
  • the required application rates of the safeners can vary within wide limits and are generally in the range from 1 to 5000 g, preferably 2 to 4000 g, in particular 3 to 2500 g of active ingredient per hectare.
  • the herbicide-safener combinations according to the invention contain the herbicides (A) and the safeners (B) in an effective content. The effects can be observed, for example, when the herbicides (A) and safener (B) are applied together, for example, as a co-formulation or as a tank mixture, but they can also be detected in the case of staggered application (split application, splitting).
  • herbicides or safeners or the herbicide-safener combinations in several portions (sequence application), eg after applications as seed treatment or pre-seed (plant) treatment or pre-emergence, followed by postemergence applications or after early postemergence applications, followed by applications in the mid or late post-emergence. Preference is given to the common or timely, separate application (application) of the herbicides
  • the weight ratio herbicide (A): safener (B) can vary within wide limits and is preferably in the range from 1: 50,000 to 500: 1, in particular 1: 8000 to 250: 1, very particularly preferably 1: 2500 to 50: 1.
  • the optimum amounts of herbicide and safener depend on the type of herbicide and safener used and on the type and stage of development of the plant stock to be treated, and can be determined on a case-by-case basis by simple, routine preliminary tests.
  • Pre-emergence treatment includes both the treatment of the area under cultivation (including any water on the acreage, eg in rice applications) before sowing / planting and the treatment of the sown, but not overgrown cultivated areas one. Preferred is the joint application with the herbicide. For this tank mixes or finished formulations can be used.
  • the seeds e.g., granules, seeds or vegetative propagules such as tubers or sprout parts with buds
  • seedlings are pretreated with the safeners (B), optionally in combination with other agrochemical active ingredients.
  • the active ingredients may be e.g. by seed dressing or the active ingredients and the seed may be added to water or other solvents, and the active ingredients e.g. be absorbed by addition or diffusion in the dipping process or by swelling or pre-germination.
  • the young plants may be e.g. by spraying, dipping or pouring with the safeners, optionally in combination with other agrochemical active ingredients, brought into contact and then transplanted and optionally treated with the herbicides (A).
  • Seedling or seedling treatment may be carried out with the safeners (B) alone or in conjunction with other agrochemical active substances - such as fungicides, insecticides or plant-strengthening agents, fertilizers or to speed up the swelling and germination processes.
  • agrochemical active substances such as fungicides, insecticides or plant-strengthening agents, fertilizers or to speed up the swelling and germination processes.
  • Pre-treatment application then again before, after or together with one or more herbicides (A) may also be used in combination with other known herbicides.
  • pre-treating the seed or seedlings an improved long-term effect of the safeners can be achieved.
  • herbicide-safener combinations of one or more herbicides (A) with one or more safeners (B).
  • those combinations according to the invention which also contain one or more further agrochemical active substances which differ from herbicides (A) and safeners (B) and which likewise have the function of a selective herbicide.
  • the preferred conditions explained below in particular for two-member combinations according to the invention also apply primarily insofar as they contain the two-membered combinations according to the invention.
  • the herbicide-safener combinations according to the invention may contain, as additional additional components, various agrochemical active compounds, for example from the group of fungicides, insecticides, acaricides, nematicides, bird repellents, soil conditioners, plant nutrients (fertilizers) and structurally different from the herbicides (A) Contain herbicides and plant growth regulators or from the group of customary in crop protection additives and formulation auxiliaries.
  • various agrochemical active compounds for example from the group of fungicides, insecticides, acaricides, nematicides, bird repellents, soil conditioners, plant nutrients (fertilizers) and structurally different from the herbicides (A) Contain herbicides and plant growth regulators or from the group of customary in crop protection additives and formulation auxiliaries.
  • Single components (A) and (B) differing herbicides in question preferably herbicidal active ingredients which are based on an inhibition of, for example, acetolactate synthase, acetyl-CoA carboxylase, cellulose synthase, enolpyruvylshikimate-3-phosphate synthase, glutamine synthetase, p Hydroxyphenylpyruvate dioxygenase, phytoene desaturase, photosystem I, photosystem II, protoporphyrinogen oxidase, can be used, as described, for example, in Weed Research 26 (1986) 441-445 or "The Pesticide Manual", 13th Edition 2003 or 14th Edition 2006 / 2007, or in that corresponding "The e-Pesticide Manual", version 4.0 (2006-07), each issued by the British Crop Protection Council, and cited therein.
  • herbicidal active ingredients which are based on an inhibition of, for example, acetolactate synthase, ace
  • acetochlor acibenzolar, acibenzolar-S-methyl, acifluorfen, acifluorfen-sodium, aclonifen, alachlor, allidochlor, alloxydim, alloxydim-sodium, ametryn, amicarbazone, amidochlor, amidosulfuron, aminocyclopyrachlor, Aminopyralid, Amitrole, Ammonium Sulfamate, Ancymidol, Anilofos, Asulam, Atrazine, Azafenidine, Azimsulfuron, Aziprotryn, BAH-043, BAS-140H, BAS-693H, BAS-714H, BAS-762H, BAS-776H, Beflubutamide, Benazoline, Benazoline ethyl, bencarbazone, benfluralin, benfuresate, bensulide, bensulfuron-methyl
  • the weight ratios of the herbicides (A) structurally different from components (A) and (B) for the herbicide-safener combination generally depend on the application rate of the herbicides and the effectiveness of the respective safeners and can vary within wide limits, for example in the Range of 1: 50,000 to 500: 1, preferably 1: 8000 to 250: 1, in particular 1: 2500 to 50: 1.
  • These mixtures can be formulated analogously to the 'components of the herbicide-safener combination with other herbicides / pesticides and as Ready-to-use formulation or tank mix with the herbicides provided and applied or be used separately as seed, soil or foliar application.
  • herbicide-safener combinations according to the invention have excellent herbicidal activity against a broad spectrum of economically important monocotyledonous and dicotyledonous harmful plants, such as weeds, grass weeds or cyperaceans, including species which are resistant to herbicidal active compounds such as glyphosate, glufosinate, atrazine , Imidazolinone herbicides, sulfonylureas, (hetero) aryloxy-aryloxyalkylcarboxylic acids or - phenoxyalkylcarboxylic acids (so-called 'fops'), cyclohexanedione oximes (so-called 'dims') or auxin inhibitors.
  • herbicidal active compounds such as glyphosate, glufosinate, atrazine , Imidazolinone herbicides, sulfonylureas, (hetero) aryloxy-aryloxyalkyl
  • the substances may be e.g. be applied in pre-sowing, pre-emergence or post-emergence, e.g. together or separately. Preferred is e.g. the postemergence application, in particular the accumulated harmful plants.
  • the spectrum of activity extends to species such as Abutilon spp., Amaranthus spp., Chenopodium spp., Chrysanthemum spp., Galium spp., Ipomoea spp., Kochia spp., Lamium spp., Matricaria spp., Pharitis spp. , Polygonum spp., Sida spp., Sinapis spp., Solanum spp., Stellaria spp., Veronica spp. Eclipta spp., Sesbania spp., Aeschynomene spp. and Viola spp., Xanthium spp., on the annual side, as well as Convolvulus, Cirsium, Rumex, and Artemisia in perennial weeds.
  • the active compounds of the herbicide-safener combinations according to the invention are applied to the surface of the earth before germination, either the emergence of the weed seedlings is completely prevented or the weeds grow up to the cotyledon stage, but then cease their growth and finally die after two to three weeks four weeks completely off.
  • the active ingredients can also be applied in rice in the water and are then absorbed by soil, shoot and root.
  • the herbicide-safener combinations according to the invention are distinguished by a rapidly onset and long-lasting herbicidal action.
  • Rainfastness of the active ingredients in the combinations according to the invention is generally favorable.
  • a particular advantage is the fact that the effective and used in combinations combinations of compounds (A) and (B) can be set so low that their soil effect is optimally low. Thus, their use is not only possible in sensitive cultures, but groundwater contamination is virtually avoided.
  • the combinations of active ingredients according to the invention a significant reduction of the required application rate of the active ingredients is made possible.
  • the herbicide-safener combinations according to the invention of the individual components (A) and (B) are outstandingly suitable for the selective control of harmful plants in rice crops.
  • the rice used here can be conventionally cultivated seed, hybrid seed, but also resistant, at least tolerant seed (mutagenic or transgenic), which can be derived from the indica or Japonica and from crosses of the two.
  • the herbicide-safener combinations according to the invention can be used in all types of administration which are customary for rice herbicides. They are particularly advantageously used in the spray application and / or in the "submerged application". In the so-called “submerged application”, the accumulation water already covers the earth at the time of application by up to 3 - 20 cm. The herbicide-safener combinations of the invention are then directly, e.g. in the form of a granulate in the water of the accumulated fields. Worldwide, the spray application is mainly used for seeded rice and the so-called submerged application, mainly for transplanted rice.
  • the herbicide-safener combinations according to the invention capture a broad, especially for rice crops specific weed spectrum.
  • genera such as Echinochloa spp., Panicum spp., Poa spp., Leptochloa spp., Brachiaria spp., Digitaria spp., Setaria spp.
  • Cyperus spp. Monochoria spp., Fimbristylis spp., Sagittaria spp., Eleocharis spp., Scirpus spp., Alisma spp., Aneilema spp., Blyxa spp., Eriocaulon spp., Potamogeton spp.
  • Echinochloa oryzicola Monochoria vaginalis
  • Eleocharis acicularis Eleocharis kuroguwai
  • Cyperus difformis Cyperus serotinus
  • Sagittaria pygmaea Alisma canaliculatum
  • Scirpus juncoides the species Echinochloa oryzicola, Monochoria vaginalis, Eleocharis acicularis, Eleocharis kuroguwai, Cyperus difformis, Cyperus serotinus, Sagittaria pygmaea, Alisma canaliculatum, Scirpus juncoides.
  • the spectrum of action extends to genera such as Polygonum spp., Rorippa spp., Rotala spp., Lindernia spp., Bidens spp., Sphenoclea spp., Dopatrium spp., Eclipta spp., Elatine spp., Gratiola spp., Lindernia spp., Ludwigia spp., Oenanthe spp., Ranunculus spp., Deinostema spp. and similar.
  • Species such as Rotala indica, Sphenoclea zeylanica, Lindernia procumbens, Ludwig prostrate, Potamogeton distinctus, Elatine triandra, Oenanthe javanica are well detected.
  • the herbicide-safener combinations according to the invention can also be used for controlling harmful plants in known plant crops or tolerant or genetically modified crop and energy crops to be developed.
  • the transgenic plants (GMOs) are usually characterized by particular advantageous properties, in addition to the
  • Resistances to the herbicide-safener combinations according to the invention for example, by resistance to plant diseases or pathogens of plant diseases such as certain insects or microorganisms such as fungi, bacteria or viruses.
  • Other special properties concern, for example, the crop in terms of quantity, quality, shelf life, and the composition of special ingredients. So are transgenic plants with increased starch content or altered quality of starch or those with others
  • the active compounds can also be used to control harmful plants in crops of known or yet to be developed mutant selection plants, as well as from crosses of mutagenic and transgenic plants.
  • transgenic crop plants which have resistance to herbicides, for example to sulfonylureas (EP-A-0257993, US-A-5013659), transgenic crops capable of producing Bacillus thuringiensis toxins (Bt toxins), those who have resistance to herbicides, for example to sulfonylureas (EP-A-0257993, US-A-5013659), transgenic crops capable of producing Bacillus thuringiensis toxins (Bt toxins), those who have resistance to herbicides, for example to sulfonylureas (EP-A-0257993, US-A-5013659), transgenic crops capable of producing Bacillus thuringiensis toxins (Bt toxins), those who have resistance to herbicides, for example to sulfonylureas (EP-A-0257993, US-A-5013659), transgenic crops capable of producing Bacillus thuringiensis toxins (Bt toxins), those who have resistance to herbicides, for example
  • nucleic acid molecules can be introduced into plasmids that allow mutagenesis or sequence alteration by recombination of DNA sequences. For example, base substitutions can be made, partial sequences removed, or natural or synthetic sequences added using the standard procedures outlined above. For the connection of the DNA fragments with one another adapters or linkers can be attached to the fragments.
  • the production of plant cells having a reduced activity of a gene product can be achieved, for example, by the expression of at least one corresponding antisense RNA, a sense RNA to obtain a cosuppression effect, or the expression of at least one appropriately engineered ribozyme which specifically cleaves transcripts of the above gene product ,
  • the synthesized protein may be located in any compartment of the plant cell.
  • the coding region can be linked to DNA sequences that ensure localization in a particular compartment.
  • sequences are known to the person skilled in the art (see, for example, Braun et al., EMBO J. 11 (1992), 3219- 3227; Wolter et al., Proc. Natl. Acad. Be. USA 85 (1988), 846-850; Sonnewald et al., Plant J. 1 (1991), 95-106).
  • the transgenic plant cells can be regenerated to whole plants by known techniques.
  • the transgenic plants may in principle be plants of any plant species, i. both monocotyledonous and dicotyledonous plants.
  • the invention therefore also relates to the use of the herbicidally active agent according to the invention for controlling harmful plants in transgenic crop plants or crop plants which exhibit tolerance through selection breeding and crosses / hybrids from both.
  • the present invention furthermore relates to a method for the selective control of undesirable plants, preferably in plant crops, in particular in rice crops (planted or sown under 'upland 1 or' paddy 1 conditions with indica and / or japonica species and hybrids / mutants / GMOs), characterized in that the components (A) and (B) of the herbicide-safener combinations according to the invention are applied to the plants (eg harmful plants such as monocotyledonous or dicotyledonous weeds, weed grasses, cyperaceans or undesired crops), the seed ( For example, grains, seeds or vegetative propagules such as tubers or Sprossmaschine with buds) or the area on which the plants grow (eg the acreage, which may also be covered by water), applied (applied), for example, together or separately.
  • the plants eg harmful plants such as monocotyledonous or dicotyledonous weeds, weed grasses, cyperaceans or undes
  • one or more safeners (B), preferably one or more, in particular a compound of formula (S-1), to (S-13), and / or from group (B) before, after or simultaneously with or the herbicide (s) (A) are applied to the plants, the seed or the area on which the plants grow (eg the acreage).
  • the Safener (B) used for seed treatment preferably one or more, in particular a compound of formula (S-1), to (S-13), and / or from group (B) before, after or simultaneously with or the herbicide (s) (A) are applied to the plants, the seed or the area on which the plants grow (eg the acreage).
  • the Safener (B) used for seed treatment is used for seed treatment.
  • Undesirable plants are understood to mean all plants that grow in places where they are undesirable. This can e.g. Harmful plants (e.g., monocotyledonous or dicotyledonous weeds, weed grasses, cyperaceans or undesirable crops), e.g.
  • herbicidal active ingredients such as glyphosate, glufosinate, atrazine, imidazolinone herbicides, sulfonylureas, (hetero-) aryloxy-aryloxyalkylcarboxylic acids or -phenoxyalkylcarboxylic acids (so-called 'fops'), cyclohexanedionoximes (so-called 'dims') or auxin inhibitors are resistant.
  • herbicidal active ingredients such as glyphosate, glufosinate, atrazine, imidazolinone herbicides, sulfonylureas, (hetero-) aryloxy-aryloxyalkylcarboxylic acids or -phenoxyalkylcarboxylic acids (so-called 'fops'), cyclohexanedionoximes (so-called 'dims') or auxin inhibitors are resistant.
  • the herbicide-safener combinations of the invention will be used selectively to control undesired plant growth, e.g. in crops such as crops, e.g. monocotyledonous crops such as cereals (e.g., wheat, barley, rye, oats, rice, corn, millet) or dicotyledonous crops such as sugar beet, sugarcane, rape, cotton, sunflowers and legumes, e.g. of the genera Glycine (eg Glycine max. (soy) as non-transgenic Glycine max.
  • crops e.g. monocotyledonous crops such as cereals (e.g., wheat, barley, rye, oats, rice, corn, millet) or dicotyledonous crops such as sugar beet, sugarcane, rape, cotton, sunflowers and legumes, e.g. of the genera Glycine (eg Glycine max. (soy) as non-transgenic Glycine
  • the invention also provides the use of the herbicide-safener combinations according to the invention for the selective control of undesired plant growth, preferably in plant crops, in particular in rice crops (planted or sown under 'upland 1 or' paddy 'conditions with indica and / or Japonica species as well as hybrids / mutants / GMOs).
  • the present invention furthermore relates to a method for improving crop plant compatibility, preferably in plant crops, in particular in rice crops (planted or sown under 'upland 1 or' paddy 'conditions with indica and / or japonica species and hybrids / mutants / GMOs ), which is characterized in that the components (A) and (B) of the herbicide-safener combinations according to the invention on the plants (eg harmful plants such as mono- or dicotyledonous weeds, weed grass, Cyperaceae or undesirable crops), the seed (eg grains , Seeds or vegetative
  • Multiplication organs such as tubers or sprouts with buds
  • the area on which the plants grow e.g., the acreage, which may also be covered by water
  • one or more safeners (B) preferably one or more, in particular a compound of formula (S-1), to (S-13), and / or from group (B) before, after or simultaneously with or the herbicide (s) (A) are applied to the plants, the seed or the area on which the plants grow (eg the acreage).
  • the safeners (B) are used for seed treatment.
  • the herbicide-safener combinations of the invention may be prepared by known methods, e.g. be prepared as mixed formulations of the individual components, optionally with further active ingredients, additives and / or customary formulation auxiliaries, which are then diluted with water in the usual way
  • Formulated individual components are prepared with water. Also possible is the staggered use (split application, splitting) of the separately formulated or partially separately formulated individual components. It is also possible to use the individual components or the herbicide-safener combinations in several portions (sequence application), eg after pre-emergence applications, followed by post-emergence applications or early post-emergence applications, followed by mid-late post-emergence applications. Preference is given to the common or timely use of the active ingredients of the respective combination, particularly preferably the common use.
  • the herbicides (A) and safeners (B) can be converted together or separately into customary formulations, such as solutions, emulsions, suspensions, powders, foams, pastes, granules, aerosols, active substance-impregnated natural and synthetic substances, microencapsulations in polymeric substances , Also to be mentioned are specific formulations for rice cultivation, such as e.g. Scattering granules, "jumbo” granules, "floating granules”, “floating” -suspoemulsions which are applied via "shaker bottles” and are dissolved and distributed via the accumulation water.
  • the formulations may contain the usual auxiliaries and additives.
  • formulations are prepared in a known manner, e.g. by mixing the active compounds with extenders, that is to say liquid solvents, liquefied gases under pressure and / or solid carriers, if appropriate using surface-active agents, that is to say emulsifiers and / or dispersants and / or foam-forming agents.
  • extenders that is to say liquid solvents, liquefied gases under pressure and / or solid carriers, if appropriate using surface-active agents, that is to say emulsifiers and / or dispersants and / or foam-forming agents.
  • organic solvents can also be used as auxiliary solvent.
  • Suitable liquid solvents are essentially: aromatics, such as xylene, toluene, alkylnaphthalenes, chlorinated aromatics or chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chloroethylenes or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, for example petroleum fractions, mineral and vegetable oils, alcohols, such as butanol or glycol, and their ethers and esters, ketones, such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents, such as dimethylformamide or dimethyl sulfoxide, and water.
  • Suitable solid carriers are: e.g. Ammonium salts and ground natural minerals, such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, and ground synthetic minerals, such as fumed silica, alumina and silicates; suitable solid carriers for granules are: e.g. crushed and fractionated natural rocks such as calcite, marble, pumice, sepiolite, dolomite and synthetic granules of inorganic and organic flours and granules of organic material such as sawdust, coconut shells, corn cobs and tobacco stalks; suitable emulsifiers and / or foam formers are: e.g.
  • nonionic and anionic emulsifiers such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, e.g. Alkylaryl polyglycol ethers, alkylsulfonates, alkylsulfates, arylsulfonates and protein hydrolysates; suitable dispersants are: e.g. Ligninsulfitablaugen and methylcellulose.
  • Adhesives such as carboxymethylcellulose, natural and synthetic, powdery, granular or latex polymers may be used in the formulations, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, as well as natural phospholipids such as cephalins and lecithins and synthetic phospholipids.
  • Other additives may be mineral and vegetable oils.
  • the herbicidal activity of the herbicide-safener combinations according to the invention can be e.g. be improved equally by surface-active substances, preferably by wetting agents from the series of fatty alcohol polyglycol ethers.
  • the fatty alcohol polyglycol ethers preferably contain 10 to 18 C atoms in the fatty alcohol radical and 2 to 20 ethylene oxide units in the polyglycol ether section.
  • Fatty alcohol polyglycol ethers can be nonionic, or ionic, for example in the form of fatty alcohol Polyglykolethersulfaten, present, for example, as alkali metal salts (eg Sodium and potassium salts) or ammonium salts, or as alkaline earth metal salts are used, such as C 2 / C 4 fatty alcohol diglykolethersulfat- sodium (Genapol ® LRO, Clariant GmbH); See, for example, EP-A-0476555, EP-A-0048436, EP-A-0336151 or US-A-4,400,196 and Proc. EWRS Symp. "Factors Affecting Herbicidal Activity and Selectivity", 227-232 (1988).
  • Nonionic fatty alcohol polyglycol ethers are, for example, 2 - 20, preferably 3 - 15 ethylene oxide units containing (C 0 - C 8) -, preferably (C 0 - C 4) -Fettalkohol- polyglycol ethers (for example isotridecyl alcohol polyglycol ether), for example from the Genapol ® X - row as Genapol ® X-030, Genapol ® X-060, Genapol ® X-080 or Genapol ® X-150 (all from Clariant GmbH).
  • Genapol ® X - row as Genapol ® X-030, Genapol ® X-060, Genapol ® X-080 or Genapol ® X-150 (all from Clariant GmbH).
  • the present invention further comprises the combination of components (A) and (B) with the aforementioned wetting agents from the series of fatty alcohol polyglycol ethers which preferably contain 10 to 18 C atoms in the fatty alcohol radical and 2 to 20 ethylene oxide units in the polyglycol ether part and nonionic or ionic (eg as fatty alcohol polyglycol ether) may be present.
  • fatty alcohol polyglycol ethers such as nonionic or ionic fatty alcohol polyglycol ethers (e.g., fatty alcohol polyglycol ether sulfates) are also useful as penetration aids and enhancers for a variety of other herbicides (see, e.g., EP-A-0502014).
  • the present invention therefore furthermore also includes the combination with suitable penetration aids and activity enhancers, preferably in a commercially available form.
  • the herbicide-safener combinations according to the invention can also be used together with vegetable oils.
  • vegetable oils refers to oils derived from oil-producing plant species, such as soybean oil, rapeseed oil, corn oil, sunflower oil, cottonseed oil, linseed oil, coconut oil, palm oil, thistle oil or castor oil, in particular Rapeseed oil understood as well as their transesterification products, for example alkyl esters such as rapeseed oil methyl ester or rapeseed oil ethyl ester.
  • the vegetable oils are preferably esters of C -C O 2 2-> preferably C12-C20 fatty acids.
  • the C O -C 22 -fatty acid esters are, for example, esters of unsaturated or saturated C O -C 22 fatty acids, especially with an even number of carbon atoms, for example erucic acid, lauric acid, palmitic acid and in particular C- ⁇ 8 fatty acids such as stearic acid, oleic acid, linoleic acid or linolenic acid.
  • Cio-C 22 fatty acid esters are esters obtained by reacting glycerol or glycol with the C O -C 22 fatty acids, such as those contained in oils from oil-plant species, for example, or Ci-C 2 o alkyl-C 1o C 22 -fatty acid esters, as obtained, for example by transesterification of the abovementioned glycerol or glycol-C 0 -C 2 2- fatty acid esters with -C 2 o-alcohols (for example methanol, ethanol, propanol or butanol) can be.
  • the transesterification can be carried out by known methods, as described for example in Rompp Chemie Lexikon, 9th edition, Volume 2, page 1343, Thieme Verlag Stuttgart.
  • Glycerol-Cio-C 2 2-fatty acid esters preferred are the uniform or mixed glycol esters and glycerol esters of Ci O -C 22 fatty acids, in particular those fatty acids with even number of carbon atoms, such as erucic acid, lauric acid, palmitic acid and in particular Ci ⁇ fatty acids such Stearic acid, oleic acid, linoleic acid or linolenic acid.
  • the present invention also comprises the combinations with the abovementioned vegetable oils, such as rapeseed oil, preferably in the form of commercially available oil-containing formulation additives, in particular those based on rapeseed oil, such as Hasten® (Victorian Chemical Company, Australia, hereinafter referred to as Hasten, main constituent: rapeseed oil ethyl ester ) Actirob ® B (Novance, France, hereinafter referred ActirobB, main ingredient: Rapsölmethylester), Rako-binol ® (Bayer AG, Germany, referred to as Rako-binol called main constituent: rapeseed oil), Renol ® (Stefes, Germany, termed Renol , Vegetable oil constituent: rapeseed oil methyl ester) or Stefes Mero® (Stefes, Germany, hereinafter referred to as Mero, main constituent: rapeseed oil methyl ester).
  • Hasten® Vic
  • Dyes such as inorganic pigments, e.g. Iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin, azo and metal phthalocyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.
  • inorganic pigments e.g. Iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin, azo and metal phthalocyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.
  • the formulations generally contain between 0.1 and 95 weight percent (wt%) of active ingredient, preferably between 0.5 and 90 wt%.
  • the individual components (A) and (B) can be used as such or in their formulations in admixture with other agrochemical active ingredients such as known herbicides for controlling unwanted plant growth, for example for controlling weeds or for controlling unwanted crops, eg finished formulations or tank mixes possible are.
  • agrochemical active ingredients such as known herbicides for controlling unwanted plant growth, for example for controlling weeds or for controlling unwanted crops, eg finished formulations or tank mixes possible are.
  • Mixtures with other known active substances such as fungicides, insecticides, acaricides, nematicides, safeners, bird repellants, plant nutrients and soil conditioners are also possible.
  • the individual components (A) and (B) can be used as such, in the form of their formulations or the use forms prepared therefrom by further dilution, such as ready-to-use solutions, suspensions, emulsions, powders, pastes and granules.
  • the application is done in the usual way, e.g. by pouring, spraying, spraying, sprinkling.
  • the active substances can be applied to the plants (for example harmful plants such as monocotyledonous or dicotyledonous weeds, weed grasses, cyperaceans or undesired crop plants), the seeds (for example grains, seeds or vegetative propagation organs such as tubers or shoot parts with buds) or the cultivated area (for example arable soil) , preferably on the green plants and plant parts and optionally on the farmland.
  • harmful plants such as monocotyledonous or dicotyledonous weeds, weed grasses, cyperaceans or undesired crop plants
  • the seeds for example grains, seeds or vegetative propagation organs such as tubers or shoot parts with buds
  • the cultivated area for example arable soil
  • One possibility of the application is the common application of the active ingredients in the form of tank mixes, wherein the optimally formulated concentrated formulations of the individual active ingredients are mixed together in the tank with water and the spray mixture obtained is applied.
  • a common herbicidal formulation of the combination according to the invention with the individual components (A) and (B) has the advantage of easier applicability, wherein the amounts of the components can be adjusted already in the optimal ratio to each other.
  • the adjuvants in the formulation can be optimally matched to one another.
  • Crop seeds were placed in sandy loam soil and covered with soil. The pots were placed in the greenhouse and kept under good growth conditions for the crops. Two weeks after sowing, the test plants were treated in the 1-3 leaf stage.
  • the active ingredients of components (A) and (B) formulated in the form of wettable powders were then sprayed onto the green parts of plants as aqueous suspensions in various dosages with a water consumption of 300 l / ha.

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  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

La présente invention concerne une association herbicide-phytoprotecteur composée des constituants (A) et (B), (A) désignant un ou plusieurs composés ou leurs sels du groupe décrit par la formule générale (I), dans laquelle R1 signifie halogène, de préférence fluor ou chlore, R2 signifie hydrogène et R3 hydroxyle ou R2 et R3 signifient, conjointement avec l'atome de carbone auquel ils sont liés, un groupe carbonyle C=O et R4 désigne hydrogène ou méthyle; et (B) désignant un ou plusieurs composés du groupe des phytoprotecteurs.
EP09777755A 2008-08-14 2009-08-08 Association herbicide-phytoprotecteur composée d'anilides de difluorométhanesulfonyle à substitution diméthoxytriazinyle Withdrawn EP2323483A2 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE102008037627A DE102008037627A1 (de) 2008-08-14 2008-08-14 Herbizid-Kombination mit Dimethoxytriazinyl-substituierten Difluormethansulfonylaniliden
PCT/EP2009/005763 WO2010017925A2 (fr) 2008-08-14 2009-08-08 Association herbicide-phytoprotecteur composée d'anilides de difluorométhanesulfonyle à substitution diméthoxytriazinyle

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EP2323483A2 true EP2323483A2 (fr) 2011-05-25

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EP09777755A Withdrawn EP2323483A2 (fr) 2008-08-14 2009-08-08 Association herbicide-phytoprotecteur composée d'anilides de difluorométhanesulfonyle à substitution diméthoxytriazinyle

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US (1) US20100062939A1 (fr)
EP (1) EP2323483A2 (fr)
JP (1) JP2011530552A (fr)
KR (1) KR20110042226A (fr)
CN (1) CN102186347A (fr)
BR (1) BRPI0917673A2 (fr)
DE (1) DE102008037627A1 (fr)
WO (1) WO2010017925A2 (fr)

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Also Published As

Publication number Publication date
WO2010017925A2 (fr) 2010-02-18
US20100062939A1 (en) 2010-03-11
JP2011530552A (ja) 2011-12-22
WO2010017925A3 (fr) 2010-10-21
BRPI0917673A2 (pt) 2015-08-18
CN102186347A (zh) 2011-09-14
DE102008037627A1 (de) 2010-02-18
KR20110042226A (ko) 2011-04-25

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