EP2205090A2 - Association herbicide-phytoprotecteur - Google Patents

Association herbicide-phytoprotecteur

Info

Publication number
EP2205090A2
EP2205090A2 EP08841223A EP08841223A EP2205090A2 EP 2205090 A2 EP2205090 A2 EP 2205090A2 EP 08841223 A EP08841223 A EP 08841223A EP 08841223 A EP08841223 A EP 08841223A EP 2205090 A2 EP2205090 A2 EP 2205090A2
Authority
EP
European Patent Office
Prior art keywords
ion
alkyl
herbicide
substituted
group
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Withdrawn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
EP08841223A
Other languages
German (de)
English (en)
Inventor
Christopher Hugh Rosinger
Erwin Hacker
Georg Bonfig-Picard
Dominique Schreiber
Christian Waldraff
Klaus-Helmut Müller
Ernst Rudolf Gesing
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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Publication date
Application filed by Bayer CropScience AG filed Critical Bayer CropScience AG
Priority to EP08841223A priority Critical patent/EP2205090A2/fr
Publication of EP2205090A2 publication Critical patent/EP2205090A2/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Withdrawn legal-status Critical Current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
    • 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
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
    • A01N47/36—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the group >N—CO—N< directly attached to at least one heterocyclic ring; Thio analogues thereof

Definitions

  • the invention relates to the technical field of crop protection agents, in particular herbicide-safener combinations, which are outstandingly suitable for use against harmful plants in crops.
  • these agents are sometimes not fully compatible with some important crop plants, such as e.g. various cereals (such as wheat, triticale, barley, rye), sugar cane, sugar beet, soy, rape corn, rice or cotton. Therefore, they can not be used in some crops to ensure the desired broad herbicidal activity against harmful plants.
  • the subject of the present invention is therefore a herbicide-safener combination containing
  • an ion of the transition metals preferably manganese, copper, zinc and iron, or (d) an ammonium ion in which optionally one, two, three or all four hydrogen atoms are represented by identical or different radicals from the group C 4) alkyl, hydroxy (Ci- C4) alkyl, (C 3 -C 6) -cycloalkyl, (Ci-C 4) alkoxy (CrC 4) alkyl, hydroxy (C 1 -C 4 ) -alkoxy- (Ci-C 4 ) -alkyl, (dC 6 ) -Mercaptoalkyl, phenyl or benzyl are substituted, wherein the aforementioned
  • Radicals optionally by one or more identical or different radicals from the group halogen, such as F, Cl, Br or I 1 nitro, cyano, azido, (C r C 6 ) alkyl, (dC 6 ) haloalkyl, (C 3 - C 6 ) -cycloalkyl, (C 1 -Ce) -alkoxy, (C 1 -Ce) -HaIOaIkOXy and phenyl are substituted, and wherein in each case two substituents on the N-
  • halogen such as F, Cl, Br or I 1 nitro, cyano, azido, (C r C 6 ) alkyl, (dC 6 ) haloalkyl, (C 3 - C 6 ) -cycloalkyl, (C 1 -Ce) -alkoxy, (C 1 -Ce) -HaIOaIkOXy and phenyl are substituted, and wherein in
  • Compound is 1-10 carbon atoms in the ring system.
  • the herbicide-safener combinations of the invention may contain additional additional components, e.g. As crop protection agents of other types and / or customary in plant protection additives and / or formulation auxiliaries, or used together with these.
  • the herbicides (A) and safeners (B) can be applied in a known manner, e.g. together (for example as a co-formulation or as a tank mixture) or also in a time-delayed manner (splitting), e.g. on the plants, plant parts, plant seeds, seed treatment or the area on which the plants grow. It is possible, e.g. the application of the individual active substances or the herbicide-safener combination in several portions (sequence application), for. Seed treatment followed by pre-emergence and / or post-emergence application, or 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. It is also possible to use the
  • 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.
  • Preferred herbicides (A) are 2-iodo-N - [(4-methoxy-6-methyl-1,3,5-triazin-2-yl) carbamoyl] benzenesulfonamide and compounds of the formula (I) in which Cation (M + )
  • an ion of the transition metals preferably manganese, copper, zinc and iron, or (d) an ammonium ion in which optionally one, two, three or all four hydrogen atoms are represented by identical or different radicals from the group C 4) alkyl, hydroxy- (Cr C4) alkyl, (C 3 -C 4) cycloalkyl, (Ci-C2) alkoxy- (Ci-C2) alkyl, hydroxy (CrC 2) alkoxy- (Ci-C 2 ) alkyl, (dC 2 ) -Mercaptoalkyl, phenyl or benzyl are substituted, whereby the before mentioned
  • Radicals optionally substituted by one or more, identical or different radicals from the group halogen, such as F, Cl, Br or I, nitro, cyano, azido, (C 1 -C 2 ) -alkyl, (C r C 2 ) -haloalkyl, (C 3 -C 4 ) -cycloalkyl, (C 1 -C 2 ) -alkoxy, (C 1 -C 2 ) -haloalkoxy and phenyl are substituted, and wherein in each case two substituents on the N-
  • halogen such as F, Cl, Br or I
  • a quaternary phosphonium ion preferably tetra - ((Ci-C4) - alkyl) phosphonium and tetraphenyl phosphonium, wherein the (Ci-C 4) alkyl radicals and the phenyl radicals optionally monosubstituted or polysubstituted by identical or different radicals from the group halogen, such as F, Cl, Br or I, (dC 2) alkyl, (CrC 2) - haloalkyl, (C 3 -C 4) cycloalkyl, (Ci-C2) alkoxy and (C 1 -C 2 ) - haloalkoxy, or (f) a tertiary sulfonium ion, preferably tri - ((C 1 -C 4 ) -alkyl) sulfonium or triphenyl-sulfonium, where the (C 1 -C 4 ) -al
  • DBU is 1 , 8-diazabicyclo [5.4.0] undec-7-ene
  • hydrocarbon radicals mentioned in the radical definitions such as alkyl, alkenyl or alkynyl, also in combinations with heteroatoms, such as in alkoxy, alkylthio, haloalkyl or alkylamino, are also straight-chain or branched, even if not expressly stated.
  • Examples of compounds which are preferably used as herbicide (A) are 2-iodo-N - [(4-methoxy-6-methyl-1,3,5-triazin-2-yl) carbamoyl] benzenesulfonamide (AO) and those described in US Pat compounds of the formula (I) below (ie the compounds (A-1 to A-35)).
  • Table A Compounds of general formula (I), wherein M + denotes the respective salt of the compound
  • herbicides (A) are 2-iodo-N - [(4-methoxy-6-methyl-1,3,5-triazin-2-yl) carbamoyl] benzenesulfonamide and compounds of the formula (I) in which the cation (M + ) is a sodium ion, a potassium ion, a lithium ion, a magnesium ion, a calcium ion, an NH 4 + ion, a (2-hydroxyeth-1-yl) ammonium ion, bis-N, N- (2-hydroxyeth-1-yl) ammonium ion, Tris-N, N, N- (2-hydroxyeth-1-yl) ammonium ion, a methylammonium ion, a dimethylammonium ion, Ion, a trimethylammonium ion, a tetramethylammonium ion, an ethylammonium ion, a die
  • herbicides (A) are 2-iodo-N - [(4-methoxy-6-methyl-1,3,5-triazin-2-yl) carbamoyl] benzenesulfonamide and compounds of the formula (I) in which the cation (M + ) is a sodium ion, a potassium ion, a magnesium ion, a calcium ion, or an NH 4 + ion.
  • herbicide (A) are the 2-iodo-N - [(4-methoxy-6-methyl-1,3,5-triazin-2-yl) carbamoyl] benzenesulfonamide and compounds of the formula (I), in which the cation (M + ), a sodium ion, a potassium ion or a NH 4 + ion.
  • the compounds of the formula (I) can exist as stereoisomers.
  • the possible stereoisomers defined by their specific spatial form, such as enantiomers, diastereomers, Z and E isomers, are all encompassed by the formula (I).
  • stereoisomers can be obtained from the mixtures obtained in the preparation by customary separation methods, for example by chromatographic separation methods. Similarly, stereoisomers can be selectively prepared by using stereoselective reactions using optically active sources and / or adjuvants. The invention thus also relates to all stereoisomers which comprises the general formula (I), but are no longer specified with their specific stereoform, and their mixtures.
  • the herbicides of group (A) inhibit the enzyme acetolactate synthase (ALS) and thus protein biosynthesis in plants.
  • the application rates are generally, for example in the range from 0.001 g to 1000 g AS / ha, preferably 0.1 g to 500 g AS / ha, particularly preferably 0.5 g to 250 g AS / ha.
  • the herbicides (A) are useful for controlling harmful plants, e.g. suitable in crops, for example in economically important crops e.g. monocotyledonous crops such as cereals (for example wheat, barley, rye, oats), rice, maize, millet or dicotyledonous crops such as sugarcane, sugarbeet,
  • monocotyledonous crops such as cereals (for example wheat, barley, rye, oats), rice, maize, millet or dicotyledonous crops such as sugarcane, sugarbeet,
  • Rapeseed, cotton, sunflower and legumes eg of the genera Glycine (eg Glycine max. (Soy) as non-transgenic Glycine max. (Eg conventional varieties such as STS varieties) or transgenic Glycine max. (Eg RR soy or LL soy) and their crosses), Phaseolus, Pisum, Vicia and Arachis, or vegetable crops from various botanical groups such as potato, leek, cabbage, carrot, tomato, onion, as well as permanent and plantation crops such as pome and stone fruit, soft fruit, wine, Hevea, bananas , Sugarcane, coffee, tea, citrus, nut plantations, turf, palm tree crops and forest crops.
  • Glycine eg Glycine max. (Soy) as non-transgenic Glycine max. (Eg conventional varieties such as STS varieties) or transgenic Glycine max. (Eg RR soy or LL soy) and their crosses
  • Phaseolus, Pisum, Vicia and Arachis or vegetable crops from various botanical groups such
  • the herbicide-safener combinations (A) + (B) are also preferred, the use in cereals (eg wheat, barley, rye, oats), rice, corn, millet, sugar beet, sugar cane is particularly preferred , Sunflower, rapeseed and cotton.
  • the herbicide-safener combinations (A) + (B) are also usable in tolerant and non-tolerant mutant cultures and tolerant and intolerant transgenic cultures, preferably of corn, rice, cereals, rapeseed and soy, eg those resistant to imidazolinone herbicides, atrazine, glufosinates or glyphosate.
  • 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) of particular interest containing one or more safeners are of particular interest.
  • the safeners which are used in an antidote effective content, reduce the phytotoxic side effects of the herbicides / pesticides used, eg. B. in economically important crops such as cereals (wheat, barley, rye, corn, rice, millet), sugar beet, sugar cane, rapeseed, cotton and soybeans, preferably cereals.
  • the radicals can be alkyl, alkoxy, haloalkyl, haloalkoxy, alkylamino, alkylthio, haloalkylthio, alkylsulfinyl, alkylsulfonyl, haloalkylsulfinyl and haloalkylsulfonyl, and the corresponding unsaturated and / or substituted radicals in the carbon skeleton each be straight-chain or branched.
  • these radicals are the lower carbon skeletons, eg having 1 to 6 C atoms, in particular 1 to 4 C atoms, or unsaturated groups having 2 to 6 C atoms, in particular 2 to 4 C atoms , prefers.
  • Alkyl radicals also in compound meanings such as alkoxy, haloalkyl, etc., mean, for example, methyl, ethyl, n- or i-propyl, n-, i-, t- or 2-butyl, pentyls, hexyls, such as n-hexyl, i-hexyl and 1, 3 Dimethylbutyl, heptyls such as n-heptyl, 1-methylhexyl and 1, 4-dimethylpentyl; 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 is, for example, vinyl, allyl, 1-methylprop-2-en-1-yl, 2-methylprop-2-en-1-yl, but-2-en-1-yl, but-3-ene-1 -yl, 1-methylbut-3-en-1-yl and 1-methyl-but-2-en-1-yl;
  • Alkynyl is, for example, 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.
  • it is a heteroaromatic ring having a heteroatom from the group N, O and S, for example pyridyl, pyrrolyl, thienyl or furyl; furthermore, it is preferably a corresponding heteroaromatic Ring with 2 or 3 heteroatoms, e.g. Pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, thiazolyl, thiadiazolyl, oxazolyl, isoxazolyl, pyrazolyl, imidazolyl and triazolyl.
  • Piperidyl or pyrrolinyl such as ⁇ 1 -pyrrolinyl, ⁇ 2 -pyrrolinyl or ⁇ 3 -pyrrolinyl, z. ⁇ 1 -pyrrolin-2-yl, ⁇ 1 -pyrrolin-3-yl, ⁇ 1 -pyrrolin-4-yl or ⁇ 1 -pyrrolin-5-yl or ⁇ 2 -pyrrolin-1-yl, ⁇ 2 - Pyrrolin-2-yl, ⁇ 2 -pyrrolin-3-yl, ⁇ 2 -pyrrolin-4-yl, ⁇ 2 -pyrrolin-5-yl or ⁇ 3 -pyrrolin-1-yl, ⁇ 3 -pyrrolin-2-yl or ⁇ 3 -pyrrolin-3-yl.
  • 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 orf ⁇ o-continuous", for example the groups benzo-1, 4-dioxan-yl, 1, 3-benzodioxol-yl, chroman-yl, 3,4-dihydro-1H-chroman-yl, 2,3-dihydro-1-benzofuran, 1, 3-dihydro-1-benzofuran -yl, indan-yl, 1, 2,3,4-tetrahydronaphthyl, and theirs on the saturated
  • Carbon units halogenated, in particular fluorinated analogues.
  • Suitable substituents for a substituted heterocyclic radical are the substituents mentioned below in question, in addition also oxo.
  • the oxo group may also be attached to the hetero ring atoms, which may exist in different oxidation states, e.g. at N and S, occur.
  • substituted by one or more radicals means one or more identical or different radicals.
  • first substituent level may, if they contain hydrocarbon-containing moieties, optionally continue there be substituted (“second level of substitution"), for example by one of the substituents as defined for the first substituent level.
  • second level of substitution may be substituted.
  • 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, (Ci-C 4) alkyl, preferably methyl or ethyl, (Ci-C 4) -haloalkyl, preferably trifluoromethyl, (Ci-C 4) alkoxy, preferably methoxy or ethoxy, (C 1 -C 4 ) -haloalkoxy, nitro and cyano.
  • 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, (C r C4) alkoxy, (C r C 4 ) - haloalkyl, (Ci-C 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-trichloromethyl-phenyl, 2,4-, 3,5-, 2,5- and 2,3-dichlorophenyl, o-, m- and p-methoxyphenyl
  • the safeners are preferably selected from the group consisting of: A) Compounds of the formula (SI) 1
  • n A is a natural number from 0 to 5, preferably 0 to 3;
  • R A 1 is halogen, (C r C 4 ) alkyl, (C r C 4 ) alkoxy, nitro or (dC 4 ) haloalkyl;
  • W A is an unsubstituted or substituted divalent heterocyclic radical from the group of the unsaturated or unsaturated five-membered ring heterocycles having 1 to 3 hetero-ring atoms of the type N or 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 2 is ORA 3 , SR A 3 or NRA 3 RA 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 with the carbonyl group in (SI) and unsubstituted or by radicals from the group (Ci-C 4 ) alkyl, (Ci-C 4 ) alkoxy or optionally Substituted phenyl is substituted, preferably a
  • R B 1 is halogen, (C 1 -C 4 ) -alkyl, (C 1 -CO-alkoxy, nitro or (C 1 -C 4 ) -haloalkyl;
  • n B is a natural number from 0 to 5, preferably 0 to 3, RB 2 ORB 3 , SR B 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, via the N atom is connected to the carbonyl group in (S-II) and is unsubstituted or substituted by radicals from the group (Ci-C 4 ) alkyl, (C- ⁇ -C 4 ) alkoxy or optionally substituted phenyl, preferably a radical of the formula ORB 3 , NHR B 4 or N (CH 3 ) 2 , in particular of the formula OR B 3 ;
  • RB 3 is hydrogen or an unsubstituted or substituted aliphatic hydrocarbon radical, preferably having a total of 1 to 18 C atoms;
  • RB 4 is hydrogen, (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkoxy or substituted or unsubstituted phenyl.
  • T B is a (C 1 or C 2 ) alkanediyl chain which is unsubstituted or substituted by one or two (C 1 -C 4 ) -alkyl radicals or by [(C 1 -C 3 ) -alkoxy] -carbonyl;
  • S2 8-quinolinoxyacetic acid
  • S2-1 mono name "cloquintocet-mexyl” (S2-1) (see Pestic Man.)
  • Rc 1 is (Ci-C 4) -alkyl, (dC 4) -haloalkyl, (C 2 -C 4) alkenyl, (C 2 -C 4) haloalkenyl, (C 3 -C 7) -cycloalkyl, preferably dichloromethyl;
  • Rc 2, rc 3 is identical or different hydrogen, (Ci-C4) alkyl, (C 2 -C 4) alkenyl, (C 2 -C 4) -alkynyl, (C r C4) -haloalkyl, ( C 2 -C 4) haloalkenyl, (C r C 4) alkylcarbamoyl (C r C4) alkyl, (C 2 -C 4) -Alkenylcarbamoyl- (Ci-C 4) alkyl, (Ci-C 4) alkoxy- (C r C4) alkyl, dioxolanyl (CrC 4 form) alkyl, thiazolyl, furyl, furylalkyl, thienyl, piperidyl, substituted or unsubstituted phenyl, or Rc 2 and Rc 3 together form a substituted or unsubstituted heterocyclic ring, preferably an oxa
  • R-29148 3-dichloroacetyl-2,2,5-thmethyl-1,3-oxazolidine from Stauffer
  • R-28725" 3-dichloroacetyl-2,2, -dimethyl-1,3-oxazolidine from Stauffer
  • PPG-1292 N-allyl-N - [(1,3-dioxolan-2-yl) -methyl] -dichloroacetamide from the company
  • TI-35 1-dichloroacetyl-azepane from TRI-Chemical RT
  • X is D is CH or N
  • RD 1 is CO-NRD 5 RD 6 or NHCO-RD 7 ;
  • RD 2 is halogen, (dC 4) -haloalkyl, (Ci-C 4) -haloalkoxy, nitro, (dC ⁇ alkyl, (C 1 -
  • R 0 3 is hydrogen, (Ci-C 4) -alkyl, (C 2 -C 4) -alkenyl or (C 2 -C 4) alkynyl;
  • RD 4 is halogen, nitro, (Ci-C 4) alkyl, (CrC 4) -haloalkyl, (Ci-C 4) -haloalkoxy, (C 3 - C 6) cycloalkyl, phenyl, (C r C 4) alkoxy, cyano, (Ci-C 4) alkylthio, (C r C4) alkyl- sulfinyl, (Ci-C 4) alkylsulfonyl, (CrC 4) -alkoxycarbonyl or (Ci-C 4)
  • R 0 6 is hydrogen, (C 1 -C 6 ) -alkyl, (C 2 -C 6 ) -alkenyl or (C 2 -C 6 ) -alkynyl, where the last three radicals mentioned by v D radicals from the group halogen, hydroxy , (C 1 -C 4 ) -alkyl, (C 1 -C 4 ) -alkoxy and (C 1 -C 4 ) -alkylthio, or
  • R D 7 is hydrogen, (Ci-C 4) alkylamino, di- (C r C 4) -alkylamino, (CrC 6) alkyl, (C 3 - C 6) -cycloalkyl, where the 2 last-mentioned radicals are substituted by VD Substituents from the group halogen, (CrC 4 ) alkoxy, halogeno (Ci-C 6 ) alkoxy and (CrC 4 ) alkylthio and in the case of cyclic radicals also (Ci-C 4 ) alkyl and (Ci-C 4 ) Haloalkyl;
  • N-acylsulfonamides for example of the following formula (SV), z. B. are known from WO 97/45016 wherein
  • R D 4 halogen, (Ci-C 4) -alkyl, (C 1 -C A) -alkoxy, CF 3;
  • ⁇ ID is 1 or 2;
  • V 0 is 0, 1, 2 or 3;
  • RD RD 8 and 9 are each independently hydrogen, (Ci-Ce) -alkyl, (C ß -C ⁇ J cycloalkyl, (C 3 -C 6) -alkenyl, (C 3 -C 6) -alkynyl, R 0 4 is halogen, (C r C4) alkyl, (dC ⁇ alkoxy, CF 3 D m is 1 or 2;
  • H) active compounds from the class of 1, 2-dihydroquinoxaline-2-ones e.g. 1-Methyl-3- (2-thienyl) -1,2-dihydroquinoxaline-2-one, 1-methyl-3- (2-thienyl) -1,2-dihydroquinoxaline-2-thione, 1- (2 -Aminoethyl) -3- (2-thienyl) -1,2-dihydroquinoxaline-2-one-hydro-chloride, 1- (2-methylsulphonylaminoethyl) -3- (2-thienyl) -1,2-dihydrochloride quinoxalin-2-one, 1- [2- (diethylamino) ethyl] -6,7-dimethyl-3- (2-thienyl) quinoxaline (S5-1), as described in WO 2005/12630,
  • NK 049 S.S'-DimethyM-methoxy-benzophenone
  • COD 1-bromo-4- (chloromethylsulfonyl) benzene
  • R ⁇ 1, RK 2, independently of one another are halogen, (CrC 4) alkyl, (Ci-C 4) -alkoxy, (C r C4) -haloalkyl, (Ci-C 4) alkylamino, di- (Ci-C 4 ) -alkylamino, nitro;
  • R ⁇ 3 , RK 4 independently of one another are hydrogen, (C 1 -C 4 ) -alkyl, (C 2 -C 6 ) -alkenyl,
  • Halobenzyl, pyridinylalkyl and alkylammonium, n ⁇ 1 0 or 1 n ⁇ 2 , n ⁇ 3 are independently 0, 1 or 2
  • RL 1 is halogen, (Ci-C 4) alkyl, (Ci-C 4) -haloalkyl, (C 1 -C 4 J -alkoxy, (CrC 4) -haloalkoxy, nitro, (Ci-C 4) alkylthio, (C r C 4) alkylsulfonyl, (Ci-C 4) alkoxycarbonyl, optionally substituted. phenyl, optionally substituted phenoxy,
  • R L 2 is hydrogen or (C 1 -C 4 ) -alkyl
  • R L 3 is hydrogen, (C 1 -C 8 ) -alkyl, (C 2 -C 4 ) -alkenyl, (C 2 -C 4 ) -alkynyl, or aryl, where each of the abovementioned C-containing radicals is unsubstituted or substituted by one or more carbon atoms a plurality of, preferably up to three, identical or different radicals from the group consisting of halogen and alkoxy is substituted; or their salts.
  • R N 1 is halogen, (C 1 -C 4 ) -alkyl, methoxy, nitro, cyano, CF 3 , OCF 3
  • Y, Z independently of one another are O or S, n N is an integer from 0 to 4,
  • RN 2 (C 1 -C 16 ) -alkyl, (C 2 -C 6 ) -alkenyl, (C 3 -C 6 ) -cycloalkyl, aryl; benzyl,
  • R N 3 is hydrogen, (C 1 -C 6 ) alkyl
  • a mixture with other known active ingredients such as fungicides, insecticides, acaricides, nematicides, bird repellents, plant nutrients and soil conditioners is also possible.
  • Some of the safeners are already known as herbicides and therefore, in addition to the herbicidal effect on harmful plants, also have a protective effect on the crop plants.
  • the weight ratio of herbicide (mixture) to safener generally depends on the application rate of herbicide and the effectiveness of the particular safener and can vary within wide limits, for example in the range from 200: 1 to 1: 200, preferably 100: 1 to 1: 100, in particular 20: 1 to 1:20.
  • the safeners can be formulated analogously to the compounds of the formula (I) or mixtures thereof with further herbicides / pesticides and provided and used as finished formulation or tank mixture with the herbicides.
  • herbicidal active ingredients (A) and safeners (B) are:
  • Particularly preferred combinations of herbicidal active compounds (A) as specified in Table A, or the herbicidal active ingredient AO and safeners (B) are those in which the safener (B) is selected from the group of safeners consisting of
  • S1-9 isoxadifen-ethyl
  • S1-1 mefenpyr-diethyl
  • S2-1 cloquintocet-mexyl
  • S3-1 cyprosulfamide
  • S1- 9 isoxadifen-ethyl
  • S3-1 Cyprosulfamide
  • the safeners (compounds of group B) of the formulas (SI) - (S-XII) are suitable for reducing the phytotoxic effects that can occur when using herbicides (A) in crops without significantly impairing the effectiveness of these herbicidal active compounds against harmful plants , As a result, 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 from 5 to 2500 g of active ingredient per hectare.
  • the herbicidal active compounds (A) and the safeners (B) can be applied together (for example as a finished formulation or in the tank-mix process) or in any desired sequence, for example by spraying, pouring and spraying or by granule scattering.
  • the weight ratio herbicide (A): safener (B) can vary within wide limits and is preferably in the range of 1: 10,000 to 10,000: 1, in particular in the range of 1: 5000 to 5000: 1 and most preferably in the range of 1: 1000 to 1000: 1.
  • the optimum amounts of herbicide and safener in each case 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.
  • the safeners (B) present in the herbicide-safener combination according to the invention can be used for pretreatment of the seed of the crop (for seed dressing, for example) or introduced into the seed furrow before sowing or together with the herbicide before or after be applied to the emergence of the plants.
  • Pre-emergence treatment includes both the treatment of the acreage (including possibly on-crop water, e.g., rice applications) prior to sowing and the treatment of the sown, but not overgrown cultivated areas.
  • 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. brought to the seed by dressing or the
  • Active ingredients and the seeds can be added to water or other solvents, and the active ingredients can be taken up, for example, by addition or diffusion in the dipping method or by swelling or pre-germination.
  • the young plants can be brought into contact, for example by spraying, dipping or pouring, with the safeners, optionally in combination with other agrochemical active substances, and subsequently 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.
  • the safeners after the
  • 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.
  • the present invention thus further provides a method for controlling unwanted plants in plant crops, which is characterized in that the components (A) and (B) of the herbicide-safener combination according to the invention on the plants (eg harmful plants such as mono- or dicots Weeds or unwanted crops), the seeds (eg grains, seeds or vegetative propagules such as tubers or sprouts with buds) or the area on which the plants grow (eg the acreage) are applied, eg together or separately.
  • the components (A) and (B) of the herbicide-safener combination according to the invention on the plants eg harmful plants such as mono- or dicots Weeds or unwanted crops
  • the seeds eg grains, seeds or vegetative propagules such as tubers or sprouts with buds
  • the area on which the plants grow eg the acreage
  • one or more safeners (B) preferably one or more, in particular one
  • the safeners (B) are used for seed treatment.
  • Undesirable plants are understood to mean all plants that grow in places where they are undesirable. These may be, for example, harmful plants (for example monocotyledonous or dicotyledonous weeds or undesired crop plants), for example those which are resistant to certain herbicidal active substances such as glyphosate, atrazine, glufosinate or imidazolinone herbicides.
  • harmful plants for example monocotyledonous or dicotyledonous weeds or undesired crop plants
  • herbicidal active substances such as glyphosate, atrazine, glufosinate or imidazolinone herbicides.
  • Avena spp. On the monocotyledonous weed side, for example, Avena spp., Alopecurus spp., Apera spp., Brachiaria spp., Bromus spp., Digitaria spp., Lolium spp., Echinochloa spp., Panicum spp., Phalaris spp., Poa spp ., Setaria spp. and Cyperus species from the contendle group and on the part of the perennial species Agropyron, Cynodon, Imperata and Sorghum and also perennial Cyperusart well grasped.
  • the spectrum of activity extends to species such as e.g. 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. and Viola spp., Xanthium spp., on the annual side, as well as Convolvulus, Cirsium, Rumex, and Artemisia in perennial weeds.
  • an effective amount of components (A) and (B) are used to control harmful plants in crops, for example, in economically important crops, e.g. monocotyledonous crops such as cereals (e.g., wheat, barley, rye, oats), rice, corn, millet, or dicotyledonous crops such as sugar beet, oilseed rape, cotton, sunflowers, and legumes, e.g. of the genera Glycine (e.g.
  • Glycine max. like non-transgenic glycines max. (e.g., conventional varieties such as STS varieties) or transgenic glycines max. (eg RR soy or LL soya) and their crosses), Phaseolus, Pisum, Vicia and Arachis, or vegetable crops from various botanical groups such as potato, leek, cabbage, carrot, tomato, onion, as well as permanent and plantation crops such as and stone fruit, berry fruit, wine, Hevea, bananas, sugar cane, coffee, tea, citrus, nut orchards, turf, palm tree crops and forest crops.
  • non-transgenic glycines max. e.g., conventional varieties such as STS varieties
  • transgenic glycines max. eg., RR soy or LL soya
  • Phaseolus, Pisum, Vicia and Arachis or vegetable crops from various botanical groups such as potato, leek, cabbage, carrot, tomato, onion, as well as permanent and plantation crops such as and stone fruit,
  • the invention also relates to the use of the herbicide-safener combinations according to the invention for controlling undesired plant growth, preferably in plant crops.
  • the herbicidal safener combinations according to the invention can be prepared by known processes, for example as mixed formulations of the individual components, if appropriate with further active ingredients, additives and / or customary formulation auxiliaries, which are then diluted with water in the customary manner, or as so-called tank mixtures by common use Dilution of the separately formulated or partially separately formulated individual components are prepared with water. Also possible is the staggered application (split application) 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 e.g. 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.
  • the herbicide-safener combination according to the invention can also be used for controlling harmful plants in crops of known or yet to be developed genetically modified plants.
  • the transgenic plants are usually characterized by particular advantageous properties, for example by resistance to certain crop protection agents, resistance to plant diseases or pathogens of plant diseases such as certain insects or microorganisms such as fungi, bacteria or viruses.
  • Other special properties relate to z. B. the crop in terms of quantity, quality, shelf life, composition and special ingredients.
  • transgenic plants with increased starch content or altered quality of the starch or those with other fatty acid composition or amino acid composition of the crop are known.
  • the application of the combinations according to the invention in economically important transgenic crops of useful and ornamental plants, eg.
  • cereals eg wheat, barley, rye, oats
  • millet e.g., rice, cassava and corn
  • sugar cane e.g wheat, barley, rye, oats
  • cotton e.g., awt, awt, awt, a, rapeseed, potato, tomato, pea and other vegetable crops.
  • 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 selective breeding.
  • the herbicides (A) and the safeners (B) may be used together or separately in common formulations e.g. be applied for spraying, pouring, spraying and seed dressing, such as solutions, emulsions, suspensions, powders, foams, pastes, granules, aerosols, active substance-impregnated natural and synthetic substances, Feinstverkapselitch in polymeric materials.
  • the formulations may contain the usual auxiliaries and additives.
  • formulations are prepared in a known manner, for example by mixing the active compounds with extenders, ie liquid solvents, liquefied gases under pressure and / or solid carriers, optionally with the use of surface-active agents, ie emulsifiers and / or dispersants and / or foam-forming agents.
  • extenders ie liquid solvents, liquefied gases under pressure and / or solid carriers
  • surface-active agents ie 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, e.g. Petroleum fractions, mineral and vegetable oils, alcohols such as butanol or glycol and their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents such as dimethylformamide or dimethyl sulfoxide, and water.
  • cyclohexane or paraffins e.g. Petroleum fractions, mineral and vegetable oils, alcohols such as butanol or glycol and their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents such as dimethylformamide or dimethyl sulfoxide, and water.
  • Suitable solid carriers are: e.g. Ammonium salts and ground natural minerals, such as kaolins, clays, talc, chalk, quartz, attapulgite, montmohllonite 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 action of the herbicide-safener combination according to the invention can be improved, for example, 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 may be present nonionic, or ionic, for example in the form of fatty alcohol Polyglykolethersulfaten, present, for example, as alkali salts (eg sodium and potassium salts) or ammonium salts, or as alkaline earth salts such as magnesium salts are used, such as C ⁇ / Cu 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 (Ci 0 - Ci 8 ) -, preferably (Ci 0 -Ci 4 ) fatty alcohol polyglycol ether (eg isotridecyl alcohol polyglycol ether), for example from 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 (for example as Fatty alcohol polyglycol ether sulfates) may be present.
  • 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 (for example as Fatty alcohol polyglycol ether sulfates) may be present.
  • Genapol ® X series such as Genapol ® X-030, Genapol ® X - C 2 / C 4 fatty alcohol diglycol ether sulfate sodium (Genapol ® LRO, Clariant GmbH) and isotridecyl alcohol polyglycol ether having 3 are preferably -060, Genapol ® X-080 and Genapol ® X-150 (all from Clariant GmbH).
  • fatty alcohol polyglycol ethers such as nonionic or ionic fatty alcohol polyglycol ethers (eg fatty alcohol polyglycol ether) are also suitable as a penetration aid and enhancer for a number of other herbicides (see, for example, EP-A-0502014). It is also known that fatty alcohol polyglycol ethers, such as nonionic or ionic fatty alcohol polyglycol ethers (eg fatty alcohol polyglycol ether sulfates), are also suitable as penetration aids and activity enhancers for a number of other herbicides (see, for example, EP-A-0502014).
  • the herbicidal action of the herbicide-safener combinations according to the invention can also be enhanced by the use of vegetable oils.
  • vegetable oils is understood to mean oils from oil-supplying 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, and
  • Transesterification products e.g. Alkyl esters such as rapeseed oil methyl ester or rapeseed oil ethyl ester.
  • the vegetable oils are preferably esters of C10-C22, preferably C12-C20 fatty acids.
  • the C O -C 22 -fatty acid esters are, for example, esters of unsaturated or saturated Cio-C 22 fatty acids, especially with an even number of carbon atoms, for example erucic acid, lauric acid, palmitic acid and in particular Cis-fatty acids such as stearic acid, oleic acid, linoleic acid or linolenic acid.
  • Ci O -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-Ci O C 22 fatty acid esters, as obtained, for example, by transesterification of the aforementioned glycerol or glycol Cio-C 2 2- fatty acid esters with dC 2 o-alcohols (eg, 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.
  • C- ⁇ -C 2 o-alkyl-Cio-C 22 fatty acid esters are preferably Methylester, ethyl ester, propyl ester, butyl ester, 2-ethyl-hexyl and dodecyl.
  • Preferred glycol and glycerol-C 20 -C 22 -fatty acid esters are the homogeneous or mixed glycol esters and glycerol esters of C 10 -C 22 -fatty acids, in particular of such even-numbered fatty acids, eg erucic acid, lauric acid, Palmitic acid and in particular Ci 8 fatty acids such as stearic acid, oleic acid, linoleic acid or linolenic acid.
  • the vegetable oils may in the herbicidal safeners of the invention comprise combinations e.g. in the form of commercially available oleaginous
  • Formulation additives in particular those based on rapeseed oil such as Hasten ® (Victorian Chemical Company, Australia, hereinbelow termed Hasten, main ingredient: rapeseed oil ethyl ester), Actirob ® B (Novance, France, hereinafter ActirobB called Main Ingredient: Rapsölmethylester) (, Rako-Binol ® Bayer AG, Germany, referred to as Rako-binol called main constituent: rapeseed oil), Renol ® (Stefes, hereinafter referred to Germany Renol, vegetable oil ingredient: Rapsölmethylester) or Stefes Mero ® (Stefes, Germany, termed Mero called main ingredient: Rapsölmethylester) be included.
  • Hasten ® Vanictorian Chemical Company, Australia, hereinbelow termed Hasten, main ingredient: rapeseed oil ethyl ester
  • Actirob ® B Novance, France, hereinafter
  • rapeseed oil preferably commercially available in the form of oil-containing formulation additives, in particular those based on rapeseed oil such as Hasten ® (Victorian Chemical Company, Australia, hereinbelow termed Hasten, main constituent: rapeseed oil ethyl ester), Actirob ® B (Novance, France, hereinafter referred to ActirobB, main component:
  • Rako-Binol ® (Bayer AG, Germany, referred to as Rako-Binol, main ingredient: rapeseed oil), Renol ® (Stefes, hereinafter referred to Germany Renol, vegetable oil ingredient: Rapsölmethylester) or Stefes Mero ® (Stefes, Germany, termed Mero called, main component: rapeseed oil methyl ester).
  • Dyes such as inorganic pigments such as iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin, azo and metal phthalocyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc can be used.
  • the formulations generally contain between 0.1 and 95 percent by weight of active compound, preferably between 0.5 and 90 percent by weight.
  • herbicides (A) and safeners (B) can be used as such or in their formulations also in admixture with other agrochemical active substances, such as known herbicides, for controlling undesired plant growth, e.g. for weed control or to control undesirable crops, e.g. Ready-to-use formulations or tank mixes are possible.
  • herbicides (A) and safeners (B) may be used as such, in the form of their formulations or the forms of use 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, parts of plants, the seed or the acreage (field soil), preferably to the seed or the green plants and plant parts and optionally additionally to the field soil.
  • One possibility of the application is the joint 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 resulting spray mixture is discharged.
  • Active ingredients (A) and safeners (B) have the advantage of easier applicability because the amounts of the components are already set in the optimum ratio to each other can be.
  • the adjuvants in the formulation can be optimally matched to one another.
  • agrochemical active substances such as herbicides, preferably herbicidal active substances which are based on an inhibition of, for example, acetolactate synthase, acetyl-coenzyme A carboxylase, PS I, PS II, HPPDO, phytoene desaturase, protoporphyrinogen oxidase, glutamine synthetase, cellulose biosynthesis, 5-enolpyruvylshikimate-3-phosphate synthetase are based as in Weed Research 26, 441-445 (1986), or "The Pesticide Manual", 13th edition, The British Crop Protection Council, 2003, or 14th Edition 2006/2007, or in the corresponding "e-Pesticide Manual", version 4 (2006), published by the British Crop Protection Council (hereinafter also referred to as "PM”), and literature cited therein.) Lists of "common names" are also available
  • Sulfonamides such as sulfonylureas are also included with salts which are formed by replacement of a hydrogen atom on the sulfonamide group by a cation.
  • salts which are formed by replacement of a hydrogen atom on the sulfonamide group by a cation.
  • acetochlor acibenzolar-S-methyl; acifluorfen (-sodium); aclonifen; AD-67; AKH 7088, ie methyl [[[1- [5- (2-chloro-4- (trifluoromethyl) phenoxy] -2-nitrophenyl] -2-methoxyethylidene] amino] oxy] acetic acid and acetic acid; alachlor; alloxydim (-sodium); ametryn; amicarbazone, amidochlor, amidosulfuron; aminopyralid; amitrol; Ammoniumpelargonate; AMS, ie ammoni
  • BAS 516H i. 5-fluoro-2-phenyl-4H-3,1-benzoxazin-4-one; beflubutamide (UBH-509), benazoline (-ethyl); bencarbazone; benfluralin; benfuresate; bensulfuron (-methyl); bensulide; bentazone; benzfendizone; benzobicyclone, benzofenap; benzofluor; benzoylprop (-ethyl); benzthiazuron; bilanaphos; bifenox; bispyribac (-sodium) (KIH-2023); borax; bromacil; bromobutide; bromofenoxim; bromoxynil; bromuron; buminafos; busoxinone; butachlor; butafenacil; butamifos; butenachlor (KH-218); buthidazole; butraline;
  • Ester derivatives e.g., butyl ester, DEH-112; cyperquat; cyprazine; cyprazole; daimuron;
  • SAN-582H dimethenamide-P; dimethylarsinic acid; dimethipin; dimetrasulfuron; dimexyflam; dinitramine; dinoseb; dinoterb; diphenamid; dipropetryn; diquat salts; dithiopyr; diuron; DNOC; eglinazine-ethyl; EL 77, i.
  • MCPA mecoprop
  • mefenacet mefluidide; mepiquat (chlorides); mesosulfuron (-methyl); mesotrione; metam; metamifop; metamitron; metazachlor; methabenzthiazuron; metham; methazole; methoxyphenone; methylarsonic acid; methyl-cyclopropene; methyldymron; methylisothiocyanate; methabenzthiazuron; metobenzuron; metobromuron; (Alpha-) metolachlor; metosulam (XRD 511); metoxuron; metribuzin; metsulfuron-methyl; molinate; monalide; monocarbamide dihydrogen sulfates; monolinuron; monuron; monosulfuron; MT 128, ie 6-chloro-N- (3 chloro-2-propenyl) -5-methyl-N
  • 310 i. 4- (2,4-dichlorobenzoyl) -1-methyl-5-benzyloxypyrazol; neburon; nicosulfuron; nipyraclofen; nitralin; nitrofen; nitrophenolate mixture; nitrofluorfen; nonanoic acid; norflurazon; orbencarb; orthosulfamuron; oxabetrinil; oryzalin; oxadiargyl
  • ICI-A0224 sulfosulfuron; TCA (-sodium); tebutam (GCP-5544); tebuthiuron; tecnacene; tefuryltrione; tembothone; tepraloxydim; terbacil; terbucarb; terbuchlor; terbumeton; Terbuthylazine; terbutryn; TFH 450, ie N, N-diethyl-3 - [(2-ethyl-6-methylphenyl) sulfonyl] -1H-1, 2,4-triazole-1-carboxamide; thenylchlor (NSK-850); thiafluamide, thiazafluron; thiazopyr (Mon-13200); thidiazimin (SN-24085); thidiazuron; thiencarbazone (-methyl); thifensulfuron (-methyl); thiobencarb; Ti 35; t
  • formulations present in commercial form may optionally be diluted in the usual way, e.g. by means of water.
  • Dusty preparations ground or spreading granules and sprayable
  • Seeds or rhizome pieces of monocotyledonous and dicotyledonous weed plants were placed in sandy soil in cardboard pots and covered with soil.
  • the formulated in the form of wettable powders or emulsion concentrates active compounds (A) and (B) were then applied as aqueous suspensions or emulsions with a water application rate of 100 to 800 l / ha in different dosages on the surface of the cover soil.
  • the pots were placed in the greenhouse and kept under good growth conditions for the weeds.
  • the optical assessment of the plant or run-on damage was carried out after emergence of the test plants after a test period of 3 to 4 weeks in comparison to untreated Controls. As the results show, the tested herbicide combinations have a good herbicidal pre-emergence activity against a broad spectrum of grass weeds and weeds.
  • Seeds or rhizome pieces of monocotyledonous and dicotyledonous weeds were placed in sandy loam soil in plastic pots, covered with soil and grown in the greenhouse under good growth conditions. Three weeks after sowing, the test plants were treated at the 2-4 leaf stage.
  • the formulated as wettable powders or as emulsion concentrates compounds of the invention were in different dosages with a
  • the herbicidal combinations according to the invention have a good herbicidal activity against the emergence of a broad spectrum of economically important weeds and weeds.
  • the combinations of the 2-iodo-N - [(4-methoxy-6-methyl-1, 3,5-triazin-2-yl) carbamoyl] benzenesulfonamide and of compounds of the formula (I) mentioned in Table A have, in particular, with the safeners of the compounds of the formulas S1-1, S1-9, S2-1 and S3-1 have very good herbicidal activity against harmful plants such as Sinapis alba, Echinochloa crus-galli, Digitaria sanguinalis, Lolium multiflorum, Chrysanthemum segetum, Setaria viridis, Polygonum convolvulus, Abutilon theophrasti, Amaranthus retroflexus, Panicum miliaceum and Avena sativa postemergence at an application rate of 100 g and less active ingredient per hectare

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Abstract

L'invention concerne une association herbicide-phytoprotecteur, contenant : (A) un ou plusieurs herbicides du groupe constitué de 2-iodo-N-[(4-méthoxy-6-méthyle-1,3,5-triazine-2-l)carbamoyle]benzolsulfonamide et de composés de formule générale (I), où le cation (M+) représente (a) un ion des métaux alcalins, de préférence lithium, sodium, potassium, ou (b) un ion des métaux alcalino-terreux, de préférence calcium et magnésium, ou (c) un ion des métaux de transition, de préférence manganèse, cuivre, zinc et fer, ou (d) un ion ammonium, dans lequel éventuellement un, deux, trois ou les quatre atomes d'hydrogène sont substitués par des radicaux identiques ou différents du groupe constitué de (C1-C4)-alkyle, hydroxy-(C1-C4)-alkyle, (C3-C6)-cycloalkyle, (C1-C4)-alcoxy-(C1-C4)-alkyle, hydroxy-(C1-C4)-alcoxy-(C1-C4)-alkyle,(C1-C4)-mercaptoalkyle, phényle ou benzyle, sachant que les radicaux précités sont éventuellement substitués par un ou plusieurs radicaux identiques ou différents du groupe constitués d'halogènes, comme F, Cl, Br ou I Nitro, cyano, azido, (C1-C6)-alkyle, (C1-C6)-haloalkyle, (C3- C6)-cycloalkyle, (C1-C6)-alcoxy, (C1-C6)-haloalcoxy et phényle, et sachant que deux substituants forment éventuellement chaque fois conjointement sur l'atome N une chaîne cyclique non substituée ou substituée, ou (e) un ion phosphonium, ou (f) un ion sulfonium, de préférence tri-((C1-C4)-alkyle)-sulfonium, ou (g) un ion oxonium, de préférence tri-((C1-C4)-alkyle)-oxonium, ou (h) éventuellement un composé ionique hétérocyclique à teneur en N, saturé ou insaturé/aromatique, une fois ou plusieurs fois annelé et/ou substitué par (C1-C4)-alkyle, avec 1 à 10 atomes de C dans la combinaison cyclique ; et (B) un ou plusieurs phytoprotecteurs. L'invention concerne également l'utilisation de cette association pour la lutte contre les plantes nuisibles.
EP08841223A 2007-10-24 2008-10-22 Association herbicide-phytoprotecteur Withdrawn EP2205090A2 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
EP08841223A EP2205090A2 (fr) 2007-10-24 2008-10-22 Association herbicide-phytoprotecteur

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
EP07020859A EP2052616A1 (fr) 2007-10-24 2007-10-24 Combinaison d'herbicide et de phytoprotecteurs
EP08841223A EP2205090A2 (fr) 2007-10-24 2008-10-22 Association herbicide-phytoprotecteur
PCT/EP2008/008927 WO2009053043A2 (fr) 2007-10-24 2008-10-22 Association herbicide-phytoprotecteur

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EA201000527A1 (ru) 2010-10-29
MX2010004534A (es) 2010-06-30
MA31788B1 (fr) 2010-10-01
CL2008003152A1 (es) 2009-03-06
CN101835379A (zh) 2010-09-15
EP2052616A1 (fr) 2009-04-29
CA2703771A1 (fr) 2009-04-30
JP2011500742A (ja) 2011-01-06
WO2009053043A2 (fr) 2009-04-30
AR068995A1 (es) 2009-12-23
AU2008315931A1 (en) 2009-04-30
BRPI0818380A2 (pt) 2014-10-07
CO6270188A2 (es) 2011-04-20
TN2010000182A1 (en) 2011-11-11
WO2009053043A3 (fr) 2010-05-20
ZA201002568B (en) 2011-02-23
KR20100090778A (ko) 2010-08-17

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