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EP2205092A2 - Combinaison herbicide - Google Patents

Combinaison herbicide

Info

Publication number
EP2205092A2
EP2205092A2 EP08841689A EP08841689A EP2205092A2 EP 2205092 A2 EP2205092 A2 EP 2205092A2 EP 08841689 A EP08841689 A EP 08841689A EP 08841689 A EP08841689 A EP 08841689A EP 2205092 A2 EP2205092 A2 EP 2205092A2
Authority
EP
European Patent Office
Prior art keywords
ion
alkyl
methyl
alkoxy
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Withdrawn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
EP08841689A
Other languages
German (de)
English (en)
Inventor
Erwin Hacker
Christian Waldraff
Dominique Schreiber
Martin Jeffrey Hills
Dieter Feucht
Klaus-Helmut Müller
Ernst Rudolf Gesing
Georg Bonfig-Picard
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
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Bayer CropScience AG filed Critical Bayer CropScience AG
Priority to EP08841689A priority Critical patent/EP2205092A2/fr
Publication of EP2205092A2 publication Critical patent/EP2205092A2/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Withdrawn legal-status Critical Current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
    • 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 present invention is in the technical field of crop protection agents which are resistant to undesired plant growth, e.g. pre-sowing (with or without incorporation), pre-emergence or postemergence in arable crops such as wheat (durum wheat and common wheat), maize, soya, sugarbeet, sugarcane, cotton, rice, beans (such as bushbeam and horse bean), flax, Barley, oats, rye, triticale, rapeseed, potato and millet (sorghum), pasture grass and green / lawns are used.
  • the invention relates to a herbicidal combination containing at least two herbicides and their use for controlling undesired plant growth.
  • substituted phenylsulfonylureas have herbicidal properties. These are e.g. phenyl derivatives which are monosubstituted or polysubstituted (for example US 4127405, WO 9209608, BE 853374, WO 9213845, EP 84020, WO 9406778, WO 02072560, US 4169719, US 4629494, DE 4038430).
  • the herbicidal activity of N- (1, 3,5-triazin-2-yl-aminocarbonyl) -arylsulfonamide against harmful plants is already at a high level, but generally depends on the application rate, the particular preparation form, each to be controlled harmful plants or the harmful plant spectrum, climatic and soil conditions, etc. Another criterion is the duration of the action or the degradation rate of the herbicide. It may also be necessary to take account of changes in the susceptibility of harmful plants, which may occur with prolonged use of the herbicides or geographically. Losses of activity in individual plants can only be compensated to a limited extent by higher application rates of the herbicides, e.g. because it reduces the selectivity of the herbicides or does not improve the efficacy even at higher application rates.
  • the object of the present invention was to provide an improved crop protection agent.
  • the present invention thus relates to a herbicide combination comprising herbicides of (A) and herbicides of (B), wherein
  • transition metals preferably manganese, copper, zinc and iron, or
  • an oxonium ion preferably tri - ((C 1 -C 4 ) -alkyl) oxonium, or (h) a saturated or unsaturated radical which is optionally mono- or polysubstituted and / or (C 1 -C 4 ) -alkyl-substituted / aromatic N-containing heterocyclic ionic compound having 1-10 C atoms in the ring system.
  • 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 + )
  • alkaline earth metals preferably calcium and magnesium
  • transition metals preferably manganese, copper
  • Zinc and iron or (d) an ammonium ion in which optionally one, two, three or all of four hydrogen atoms by identical or different radicals from the group (Ci-C 4) alkyl, hydroxy- (d- C4) alkyl, (C 3 -C 4) cycloalkyl, (Ci-C 2) - Alkoxy (C 1 -C 2 ) alkyl, hydroxy (Ci-C 2 ) alkoxy (Ci-C 2 ) alkyl, (Ci-C 2 ) -Mercaptoalkyl, phenyl or benzyl are substituted, whereby the before mentioned
  • Radicals optionally by one or more, identical or different radicals from the group halogen, such as F, Cl, Br or I, nitro, cyano, azido, (Ci-C 2 ) alkyl, (CrC 2 ) haloalkyl, (C 3 - C 4 ) -cycloalkyl, (dC 2 ) -alkoxy, (dC 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 - ((C- ⁇ -C 4) - alkyl) phosphonium and tetraphenyl phosphonium, wherein the (Ci-C 4) alkyl radicals and the phenyl radicals optionally monosubstituted or polysubstituted by identical or different residues from the group halogen, such as F, Cl, Br or I, (C r C 2) alkyl, (CrC 2) - haloalkyl, (C 3 -C 4) cycloalkyl, (Ci-C 2) - alkoxy and (C r C 2) - haloalkoxy substituted, or (f) a tertiary sulfonium ion, preferably tri - ((Ci-C4) -alkyl) - or sulfonium triphenyl sulfonium, wherein the (C- ⁇ - C quaternary
  • Haloalkyl, (C 3 -C 4 ) -cycloalkyl, (CrC 2 ) -alkoxy and (C 1 -C 2 ) -haloalkoxy are substituted, or (h) a cation from the series of the following heterocyclic compounds, such as pyridine, quinoline, 2-methylpyridine, 3-methylpyridine, 4-methylpyridine, 2,4-dimethylpyridine, 2,5-dimethylpyridine, 2,6-dimethylpyhdine, 5 Ethyl 2-methylpyridine, piperidine, pyrrolidine, morpholine,
  • DBU 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)).
  • 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 a NH 4 + ion.
  • herbicide (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 + ), in which the cation (M + ) is a sodium ion, a potassium ion or a NH 4 -lon.
  • herbicides (A) and / or (B) may vary depending on the nature and linkage of the
  • Stereoisomers 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). If, for example, one or more alkenyl groups are present, diastereomers (Z and E isomers) can occur. For example, if one or more asymmetric carbon atoms are present, enantiomers and diastereomers may occur.
  • 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, the herbicides (A) and / or (B), but no longer with their specific stereoform, and mixtures thereof.
  • the herbicide combinations of the invention may contain additional additional components, e.g. As agrochemical agents of other types and / or customary in plant protection additives and / or formulation auxiliaries, or used together with these.
  • the herbicidal combinations according to the invention contain the herbicides (A) and (B) in an effective content and / or have synergistic effects.
  • the synergistic effects may e.g. when co-application of the herbicides (A) and (B) are observed, for example, as a co-formulation or as a tank mixture, but they can also be detected in a split-time application (splitting). It is also possible to use the herbicides or herbicide 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 joint or the timely application of the herbicides (A) and (B) of the respective combination.
  • the synergistic effects allow a reduction in the application rates of the individual herbicides, a higher potency at the same rate, the control of previously unrecognized species (gaps), the control of species, the tolerances or resistances to single or multiple herbicides have, an extension of the period of application and / or a reduction in the number of necessary individual applications and - as a result for the user - economically and ecologically more advantageous weed control systems.
  • the combinations of herbicides (A) + (B) according to the invention make possible synergistic increases in activity which go far and unexpectedly beyond the effects achieved with the individual herbicides (A) and (B).
  • 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.
  • the herbicides of group (A) inhibit the enzyme acetolactate synthase (ALS) and thus protein biosynthesis in plants.
  • the application rates are generally lower, for example in the range from 0.01 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 of group (B) influence, for example, gibberellin biosynthesis, acetyl-CoA-carboxylase, p-hydroxyphenyl-pyruvate-dioxygenase and are suitable for both pre-emergence and postemergence use.
  • Applications at application rates of 0.01 g to 10000 g AS / ha of the herbicides (B), preferably the compounds B (1-1) to B (4-1) is pre-and post-emergence a relatively wide range of harmful plants , eg on annual and perennial, monocotyledonous or dicotyledonous weeds as well as on unwanted crops.
  • the application rates are generally lower, z. B. in the range of 0.1 g to 5000 g AS / ha, preferably 0.5 g to 3000 g AS / ha, more preferably 1 g to 2000 g AS / ha.
  • herbicides (A) with one or more herbicides (B) are further preferred.
  • combinations of herbicides (A) with one or more herbicides (B) according to the scheme: (AO) + (B1-1), (AO) + (B1-2), (AO) + (B4-1) , (A-1) + (B1-1), (A-1) + (B1-2), (A-1) + (B4-1), (A-35) + (B1-1), ( A-35) + (B1-2), (A-35) + (B4-1).
  • those combinations according to the invention which also contain one or more other herbicides (A) and (B) different agrochemical active compounds, which also have the function of a selective herbicide.
  • herbicides according to the invention various agrochemical active ingredients, for example from the group of Safeners, fungicides, insecticides, structurally from the herbicides (A) and (B) different herbicides and plant growth regulators or from the group of customary in plant protection additives and formulation auxiliaries
  • herbicides for example, the following of the herbicides (A) and (B) structurally different herbicides in question, preferably herbicidal active ingredients based on an inhibition of, for example, acetolactate synthase, acetyl coenzyme A carboxylase, PS I 1 PS II, HPPDO, phytoene desaturase, protoporphyrinogen oxidase, glutamine synthetase, cellulose biosynthesis, 5-enolpyruvylshikimate-3-phosphate synthetase, as described, for example, in Weed Research 26, 441-445 (1986) or "The Pesticide Manual”.
  • acetolactate synthase acetyl coenzyme A carboxylase
  • PS I 1 PS II HPPDO
  • phytoene desaturase phytoene desaturase
  • protoporphyrinogen oxidase protoporphyrinogen oxidase
  • glutamine synthetase glutamine synthe
  • Sulf Bei Sulfonamides such as sulfonylureas also include salts 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 [[[1- [5- [2-chloro-4- (trifluoromethyl) -phenoxy] -2-nitrophenyl] - 2-methoxyethylidene] amino] oxy] acetic acid and acetic acid methyl ester; alachlor; ametryn; amicarbazone, amidochlor, amidosulfuron; aminopyralid; amitrol;
  • Ammoniumpelargonate AMS 1 ie ammonium sulfamate; ancimidol; anilofos; asulam; atrazine; aviglycine; azafenidin, azimsulfuron (DPX-A8947); aziprotryn; barban; BAS 516H, ie 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-
  • borax bromacil; bromobutide; bromofenoxim; bromoxynil; bromuron; buminafos; busoxinone; butachlor; butafenacil; butamifos; butenachlor (KH-218); buthidazole; butraline; butylate; cafenstrole (CH-900); caloxydim; carbetamide; carfentrazone (-ethyl); catechin; CDAA, i. 2-chloro-N, N-di-2-propenylacetamide;
  • CDEC 1 ie diethyldithiocarbamic acid 2-chloroallyl ester; chlormesulone; chlomethoxyfen; chloramben; chlorazifop-butyl; chlorbromuron; chlorbufam; chlorfenac; chlorfenprop; chlorflurecol (-methyl); chlorflurenol (-methyl); chloridazon; chlorimuron (-ethyl); chlormequat (chlorides); chlornitrofen; chlorophthalim (MK-616); chlorotoluron; chloroxuron; chlorpropham; chlorsulfuron; chlorthal-dimethyl; chlorthiamid; chlorotoluron; cinidone (-methyl and -ethyl); cinmethylin; cinosulfuron; clefoxydim; clodinafop and its ester derivatives (eg clodinafop-propargyl); clofencet; clomazone; clo
  • dimethenamide-P dimethylarsinic acid; dimethipin; dimetrasulfuron; dimexyflam; dinitramine; dinoseb; dinoterb; diphenamid; dipropetryn; diquat salts; dithiopyr; diuron; DNOC; eglinazine-ethyl; EL 77, ie, ⁇ -cyano-i, i-dimethyl-ethyl-N-methyl-1H-pyrazole-carboxamide; endothal; epoprodan; EPTC; esprocarb; ethalfluralin; ethametsulfuron-methyl; ethephon; Ethidimuron; ethiozin; ethofumesate; ethoxyfen and its esters (eg ethyl ester,
  • MCPA mecoprop
  • mefenacet mefluidide; mepiquat (chlorides); mesosulfuron (-methyl); 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-phenyl-3-
  • 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
  • RP-020630 oxadiazon; oxasulfuron; oxaziclomefone; oxyfluorfen; paclobutrazol; paraquat (dichlorides); pebulate; pelargonic acid; pendimethalin; penoxulam; pentachlorophenol; Pentanochlor; pentoxazone; perfluidone; pethoxamid; phenisopham; phenmedipham; picloram; picolinafen; piperophos; piributicarb; pirifenop-butyl; pretilachlor; primisulfuron (-methyl); probenazole; procarbazone-
  • 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 safeners are preferably selected from the group consisting of:
  • 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;
  • WA is an unsubstituted or substituted divalent heterocyclic radical from the group of unsaturated or unsaturated five-membered ring heterocycles with 1 to 3 hetero ring atoms of the type N or O, where at least one N atom and at most one O atom are contained in the ring, preferably a radical from the group (W A 1 ) to (W A 4 ),
  • RA 2 is OR A 3 , SR A 3 or NR A 3 R A 4 or a saturated or unsaturated 3- to 7-membered heterocycle having at least one N atom and up to 3 heteroatoms, preferably from the group O and S, the via the N atom with the carbonyl group in (SI) 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 ORA 3 , NHRA 4 or N (CH 3 ) 2 , in particular of the formula OR A 3 ;
  • 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
  • RA 5 is H, (C 1 -C 6 ) -alkyl, C 1 -C 8 (haloalkyl), (C 1 -C 4 ) -alkoxy (C 1 -C 8 ) -alkyl, cyano or COORA 9 , wherein R A is 9 hydrogen, (dC 8) alkyl, (dC 8) -haloalkyl, (C 1 -C 4) -
  • RB 1 is halogen, (C 1 -C 4 ) -alkyl, (C 1 -C 4 ) -alkoxy, nitro or (C 1 -C 4 ) -haloalkyl;
  • n B is a natural number from 0 to 5, preferably 0 to 3;
  • 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;
  • TB 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 substituted with [(C- ⁇ -C 3 ) alkoxy] carbonyl;
  • S2 8-quinolinoxyacetic acid
  • S2-1 5-chloro-8-quinolinoxy acetic acid (1-methylhexyl) ester
  • S2-2 5-chloro-8-quinolinoxy acetic acid
  • Rc 1 is (Ci-C 4) alkyl, (Ci-C 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, (C r C4) alkyl, (C 2 -C 4) alkenyl, (C 2 -C 4) -alkynyl, (C r C4) -haloalkyl, ( C 2 -C 4) haloalkenyl, (CrC ⁇ alkylcarbamoyl- (Ci-C 4) alkyl, (C 2 -C 4) -Alkenylcarbamoyl- (C 1 -C 4) alkyl, (Ci-C 4) Alkoxy- (C 1 -C 4 ) -alkyl, dioxolanyl- (C 1 -C 4 ) -alkyl, thiazolyl, furyl, furylalkyl, thienyl, piperidyl, substituted or unsubstituted phenyl, or Rc 2 and Rc 3 together form a substituted or unsubstituted hetero
  • R-29148 3-dichloroacetyl-2,2,5-trimethyl-1,3-oxazolidine from Stauffer
  • R-28725" 3-dichloroacetyl-2,2, -dimethyl-1,3-oxazolidine from Stauffer
  • TI-35 1-dichloroacetyl-azepane from TRI-Chemical RT
  • XD is CH or N
  • R D 1 is CO-NRD 5 RD 6 or NHCO-R 0 7 ;
  • RD 2 is halogen, (C r C4) -haloalkyl, (dC ⁇ haloalkoxy, nitro, (Ci-C 4) -alkyl, (C 1 -
  • R 0 3 is hydrogen, (C 1 -C 4 ) -alkyl, (C 2 -C 4 ) -alkenyl or (C 2 -C 4 ) -alkynyl;
  • R 0 4 is halogen, nitro, (Ci-C 4) -alkyl, (C r C4) -haloalkyl, (CrC 4) -haloalkoxy, (C 3 - C 6) cycloalkyl, phenyl, (C r C 4 ) alkoxy, cyano, (C r C4) alkylthio, (C r C4) alkyl- sulfinyl, (Ci-C 4) alkylsulfonyl, (Ci-C 4) alkoxycarbonyl or (CrC 4) alkylcarbonyl ;
  • R 0 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 ) -Cycloalkeny
  • RD 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 are represented by v D radicals from the group consisting of halogen, hydroxy, (Cr C 4 ) alkyl, (Ci-C 4 ) alkoxy and (C r C 4 ) alkylthio are substituted, or
  • R D 7 is hydrogen, (Ci-C 4) alkylamino, di- (C r C 4) alkylamino, (dC 6) alkyl, (C 3 - C ⁇ J -cycloalkyl, where the 2 last-mentioned radicals are substituted by v substituents D from the group halogen, (C 1 -C 4 ) -alkoxy, halogeno (C 1 -C 6 ) -alkoxy and (C 1 -C 4 ) -alkylthio and in the case of cyclic radicals also (C 1 -C 4 ) -alkyl and (C r C 4 ) -haloalkyl are substituted;
  • RD 7 (CrC ⁇ JAlkyl, (Ca-C ⁇ JCycloalkyl, where the latter two radicals by v D substituents selected from the group consisting of halogen, (CrC 4 ) alkoxy, halogeno (C- ⁇ -C 6 ) alkoxy and
  • RD 4 is halogen, (C r C 4 ) alkyl, (CrC 4 ) alkoxy, CF 3; m is D 1 or 2; v D is 0, 1, 2 or 3; such as
  • R 0 8 and RD 9 independently of one another are hydrogen, (C 1 -C 8 ) -alkyl, (C 3 -Ce) -
  • R 0 4 halogen, (Ci-C 4) alkyl, (C 1 -C 4) alkoxy, CF 3 D m is 1 or 2;
  • Ethyl 3,4,5-triacetoxybenzoate 3,5-dimethoxy-4-hydroxybenzoic acid, 3,5-dihydroxybenzoic acid, 4-hydroxysalicylic acid, 4-fluorosilicic acid, 1, 2-dihydro-2-oxo-6-trifluoromethylpyridine-3 carboxamide, 2-hydroxycinnamic acid, 2,4-dichlorocinnamic acid, as described in WO 2004084631, WO 2005015994, WO 2006007981, WO 2005016001;
  • H) active compounds from the class of 1, 2-dihydroquinoxaline-2-ones e.g. 1-Methyl-3- (2-thienyl) -1,2-dihydroquinoxalin-2-one, 1-methyl-3- (2-thienyl) -1,2-dihydroquinoxaline-2-thione, 1- (2 -Aminoethyl) -3- (2-thienyl) -1,2-dihydroquinoxalin-2-one hydrochloride, 1- (2-methylsulphonylaminoethyl) -3- (2-thienyl) -1,2-dihydrochloride quinoxalin-2-one as described in WO 2005/12630,
  • RK 1, RK 2, independently of one another are halogen, (Ci-C 4) alkyl, (Ci-C 4) alkoxy, (Cr C4) -haloalkyl, (CrC 4) alkylamino , Di- (C 1 -C 4 ) -alkylamino, nitro;
  • RK 1, RK 2 independently of one another are halogen, (Ci-C 4) alkyl, (Ci-C 4) alkoxy, (Cr C4) -haloalkyl, (CrC 4) alkylamino , Di- (C 1 -C 4 ) -alkylamino, nitro;
  • R ⁇ 3 , R K 4 independently of one another are hydrogen, (C 1 -C 4 ) -alkyl, (C 2 -C 6 ) -alkenyl, (C 2 -C 4 ) -alkynyl, cyanoalkyl, (C 1 -C 4 ) -haloalkyl , Phenyl, nitrophenyl, benzyl, halobenzyl, pyridinylalkyl and alkylammonium, n ⁇ 1 0 or 1 n ⁇ 2 , n ⁇ 3 are independently 0, 1 or 2
  • R L 1 is halogen, (C 1 -OO -alkyl, (Ci-C 4) -haloalkyl, (C r C4) alkoxy, (dC 4) haloalkoxy,
  • 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,
  • R N 2 is (C 1 -C 16 ) -alkyl, (C 2 -C 6 ) -alkenyl, (C 3 -C 6 ) -cycloalkyl, aryl; Benzyl, halobenzyl,
  • R N 3 is hydrogen, (C 1 -C 6 ) alkyl
  • O one or more compounds from the group: 1, 8-naphthalic anhydride, O, O-diethyl S-2-ethylthioethyl phosphorodithioate (disulfone), 4-chlorophenyl methylcarbamate (mephenate), O, O-diethyl-O-phenylphosphorotioat (Dietholate ), 4-carboxy-3,4-dihydro-2H-1-benzopyran-4-acetic acid (CL-304415, CAS Regno: 31541-57-8)
  • Cyanomethoxyimino (phenyl) acetonitrile (Cyometrinil), 1, 3-dioxolan-2-ylmethoxyimino (phenyl) acetonitrile (oxabetrinil), 4 l -chloro-2,2,2-trifluoroacetophenone-O-1,3-dioxolan-2-ylmethyloxime (Fluxofenim), 4,6-dichloro-2-phenylpyrimidine (fenclorim), benzyl 2-chloro-4-trifluoromethyl-1,3-thiazole-5-carboxylate (flurazole), 2-dichloromethyl-2-methyl-1, 3-dioxolane (MG-191),
  • 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.
  • the combinations according to the invention have an excellent herbicidal activity against a broad spectrum of economically important monocotyledonous and dicotyledonous harmful plants, such as weeds, including species which are resistant to herbicidal active substances such as glyphosate, glufosinate, atrazine or imidazolinone herbicides. Even difficult to control perennial weeds, which expel from rhizomes, rhizomes or other permanent organs, are well detected by the active ingredients.
  • the substances can be applied, for example, in pre-sowing, pre-emergence or post-emergence processes, for example jointly or separately. For example, the application is postemergence, in particular on the accumulated harmful plants.
  • 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.
  • species such as e.g. Abutilon spp., Amaranthus spp., Chenopodium spp., Chrysanthemum spp., Galium spp., Ipomoea
  • the compounds according to the invention are applied to the surface of the earth before germination, then 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 off completely after a lapse of three to four weeks.
  • Upon application of the active ingredients to the green parts of the plants postemergence also occurs very quickly after treatment, a drastic halt in growth and the weed plants remain in the existing stage of application growth stage or die after a certain time completely, so that in this way one for the crops harmful weed competition is eliminated very early and sustainably.
  • the herbicidal compositions according to the invention are distinguished by a rapidly onset and long-lasting herbicidal action.
  • the 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 contaminations are virtually avoided.
  • By 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 effect in the combinations is stronger than the expected sum of the effects of the individual herbicides used.
  • the synergistic effects allow a reduction in the application rate, the control of a broader spectrum of weeds and weeds, a faster use of herbicidal activity, a longer lasting effect, better control of harmful plants with only one or a few applications and an extension of the possible period of application.
  • the use of funds also reduces the amount of harmful ingredients, such as nitrogen or oleic acid, and their entry into the soil.
  • herbicidal compositions containing the following herbicidally active compounds (A) + (B) + (a derivative of (A) and (B) structurally different herbicidally active compound (C, each with "Common Name ")) and / or herbicides and safeners (S) containing the following compounds (A) + (B) + (C) + (S):
  • the agents for combating harmful plants can be used in known plant crops or tolerant or genetically modified crops to be developed.
  • the transgenic plants are usually characterized by particular advantageous properties, in addition to the resistance to the inventive compositions, 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 relate to z. B. the crop in terms of quantity, quality, shelf life, composition and special ingredients. So are transgenic plants with increased starch content or altered quality of the starch or those known with other fatty acid composition of the crop.
  • the active compounds can also be used to control harmful plants in crops of known or yet to be developed mutant-selected plants.
  • Bacillus thuringiensis toxins Bacillus thuringiensis toxins (Bt toxins) which render plants resistant to certain pests (EP-A-0142924,
  • nucleic acid molecules can be introduced into plasmids that have a mutagenesis or a sequence change by recombination of DNA sequences.
  • z For example, base substitutions are made, partial sequences are removed, or natural or synthetic sequences are added.
  • adapters or linkers can be attached to the fragments.
  • 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.
  • DNA molecules may be used which comprise the entire coding sequence of a gene product, including any flanking sequences that may be present, as well as DNA molecules which comprise only parts of the coding sequence, which parts must be long enough to be present in the cells to cause an antisense effect. It is also possible to use DNA sequences which have a high degree of homology to the coding sequences of a gene product, but are not completely identical.
  • the synthesized protein may be located in any compartment of the plant cell. But to achieve the localization in a particular compartment, z.
  • the coding region can be linked to DNA sequences that ensure localization in a particular compartment.
  • sequences are known to those skilled in the art (see, for example, Braun et al., EMBO J. 11 (1992), 3219-3227; Wolter et al., Proc. Natl. Acad., U.S.A. 85 (1988), 846-850; Sonnewald et al., Plant J. 1 (1991), 95-106).
  • the transgenic plant cells can be whole by known techniques Plants are regenerated.
  • the transgenic plants may in principle be plants of any plant species, ie both monocotyledonous and dicotyledonous plants.
  • the present invention further provides a method for controlling undesirable plants, preferably in plant crops, which is characterized in that the herbicides (A) and (B) of the herbicidal combination according to the invention on the plants (eg harmful plants such as mono- or dicotyledonous weeds or undesirable crops), the seeds (eg grains, seeds or vegetative propagules such as tubers or shoot parts with buds) or the area on which the plants grow (eg the cultivated area), eg together or separately.
  • One or more herbicides (A) may be applied to the plants, the seed or the area on which the plants grow (e.g.
  • Undesirable plants are understood to mean all plants that grow in places where they are undesirable. This can e.g. Harmful plants (e.g., mono- or dicotyledonous weeds or undesired crops), e.g. also those which are resistant to certain herbicidal active substances such as glyphosate, atrazine, glufosinate or imidazolinone herbicides.
  • Harmful plants e.g., mono- or dicotyledonous weeds or undesired crops
  • certain herbicidal active substances such as glyphosate, atrazine, glufosinate or imidazolinone herbicides.
  • the herbicidal 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, oilseed rape, cotton, sunflowers, and legumes, e.g. of the
  • Genera Glycine eg Glycine max. (Soy) as non-transgenic Glycine max (eg conventional strains such as STS strains) or transgenic Glycine max (eg RR soy or LL soybean) and their crosses), Phaseolus, Pisum, Vicia and Arachis, or vegetable crops from various botanical groups such as potato, leek, cabbage, carrot, tomato, onion.
  • the application is preferably carried out on the accumulated harmful plants (for example, weeds or unwanted crops), in particular before the emergence of (desired) crops.
  • the invention also provides the use of the herbicidal combinations according to the invention for controlling unwanted plant growth, preferably in plant crops.
  • the herbicide combinations of the invention may be prepared by known methods, e.g. be prepared as mixed formulations of the individual components, optionally with other active ingredients, additives and / or customary formulation auxiliaries, which are then diluted with water used in the usual way, or prepared as so-called tank mixes by co-diluting the separately formulated or partially separately formulated components with water become. 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 herbicides or herbicide 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.
  • the herbicides (A) and (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.
  • 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, that is to say 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 that is to say 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.
  • 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, 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-type polymers can be used in the formulations.
  • Other additives may be mineral and vegetable oils.
  • the herbicidal action of the herbicidal combinations 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.
  • the fatty alcohol polyglycol ethers may be nonionic, or ionic, for example in the form of fatty alcohol Polyglykolethersulfaten, present, for example, as alkali metal salts (e
  • Sodium and potassium salts) or ammonium salts, or as alkaline earth salts such as magnesium salts are used, such as Ci 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 14) -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 (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 Polyglykolethersulfate) as a penetration aid and Impact enhancers are suitable for a number of other herbicides (see, for example, EP-A-0502014).
  • 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 herbicidal action of the herbicidal combinations according to the invention can also be enhanced by the use of vegetable oils.
  • vegetable oils refers to 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 their 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 Cio-C 22 fatty acids obtained as they are, for example, in oils from oil-plant species, or Ci-C 2 o alkyl CIOC 22 -fatty acid esters, such as by transesterification of the abovementioned glycerol or glycol-C 0 -C 22, for example, - fatty acid esters with -C 2 o-alcohols (for example methanol, ethanol, propanol or butanol) can be obtained.
  • 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 1 -C 2O alkyl-Cio-C 22 fatty acid esters are preferably Methylester, ethyl ester, propyl ester, butyl ester, 2-ethyl-hexyl and dodecyl.
  • glycol and Glycerol-Cio-Caa-fatty acid esters preferred are the uniform or mixed glycol esters and glycerol esters of Ci O -C 22 fatty acids, especially those fatty acids with even number of carbon atoms, such as erucic acid, lauric acid, palmitic acid and especially C- ⁇ 8 fatty acids such as stearic acid, oleic acid, linoleic acid or linolenic acid.
  • the vegetable oils can be present in the inventive herbicidal compositions, for example in the form of commercially available oil-containing 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 component:
  • Hasten Victorian Chemical Company, Australia, hereinbelow termed Hasten, main ingredient: rapeseed oil ethyl ester
  • Actirob ® B Novance, France, hereinafter ActirobB called, 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) may be included.
  • the present invention comprises 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 ® (called Bayer AG, Germany, referred to as Rako-binol, main ingredient: rapeseed oil), Renol ® (Stefes, Germany, termed Renol, vegetable oil ingredient : Rapeseed oil methyl ester) or Stefes Mero® (Stefes, Germany, hereinafter referred to as Mero, main component: rapeseed oil methyl ester).
  • Hasten® Vanictorian Chemical Company, Australia, here
  • Dyes such as inorganic pigments, e.g. Iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin, azo and
  • Metal phthalocyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc can be used.
  • the formulations generally contain between 0.1 and 95 percent by weight of active compound, preferably between 0.5 and 90 percent by weight.
  • the herbicides (A) and (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.
  • the herbicides (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 or undesired crop plants), the seed (for example grains, seeds or vegetative propagation organs such as tubers or shoot parts with buds) or the cultivated area (for example field soil), preferably to the green plants and parts of plants and, where appropriate, on the
  • Farmland 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 of herbicides (A) and (B) according to the invention has the advantage of easier applicability, wherein the Quantities of the components can already be set in the optimum ratio to each other.
  • the adjuvants in the formulation can be optimally matched to one another.
  • 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 damage and / or the emergence damage occurred after emergence of the test plants after a test time 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.
  • the herbicide combinations of the 2-lodo-N - [(4-methoxy-6-methyl-1,3,5-triazin-2-yl) carbamoyl] benzenesulfonamide and of the compounds of the formula (I) mentioned in Table A have Compounds of group B have very good synergistic herbicidal activity against harmful plants such as Sinapis alba, Chrysanthemum segetum, Avena sativa, Stellaria media, Echinochloa crus-galli, Lolium multiflorum, Setaria viridis, Abutilon theophrasti, Amaranthus retroflexus and Panicum miliaceum pre-emergence at an application rate of 100 g and less active substance per hectare.
  • Seeds or rhizome pieces of monocotyledonous and dicotyledonous weeds were placed in sandy loam soil in plastic pots, covered with soil and covered in soil
  • 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 herbicide combinations of the 2-iodo-N - [(4-methoxy-6-methyl-1, 3,5-thazin-2-yl) carbamoyl] benzenesulfonamide and of compounds of the formula (I) mentioned in Table A have with Group B compounds have very good synergistic 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 one Application rate of 100 g and less active substance per hectare.

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Abstract

La présente invention concerne une combinaison herbicide contenant les constituants (A) et (B). (A) représente un ou plusieurs agents herbicides choisis dans le groupe comprenant le 2-iodo-N-[(4-méthoxy-6-méthyl-1,3,5-triazin-2-yl)carbamoyl]benzène sulfonamide et des composés de formule générale (I) dans laquelle le cation (M+) est : (a) un ion de métal alcalin, de préférence un ion de lithium, sodium, potassium; ou (b) un ion de métal alcalino-terreux, de préférence un ion de calcium ou magnésium; ou (c) un ion de métal de transition, de préférence un ion de manganèse, cuivre, zinc ou fer; ou (d) un ion ammonium, éventuellement un, deux, trois, voire les quatre atomes d'hydrogène étant substitués par des radicaux identiques ou différents choisis dans le groupe contenant (C1-C4)-alkyle, hydroxy-(C1-C4)-alkyle, (C3-C6)-cycloalkyle, (C1-C4)-alcoxy-(C1-C4)-alkyle, hydroxy-(C1-C4)-alcoxy-(C1-C)-alkyle, (C1-C6)-mercaptoalkyle, phényle ou benzyle, les radicaux mentionnés précédemment étant éventuellement substitués par un ou plusieurs radicaux identiques ou différents choisis dans le groupe qui comprend un halogène tel que F, Cl, Br ou I, nitro, cyano, azido, (C1-C6)-aIkyIe, -(C1-C6) haloalkyle, (C3-C6)-cycloalkyle, (C1-C6)-alcoxy, (C1-C6)-haloalcoxy et phényle, et respectivement deux substituants formant ensemble au niveau de l'atome de N éventuellement un cycle substitué ou non; 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) un composé ionique hétérocyclique annelé une ou plusieurs fois et/ou substitué par (C1-C4)-alkyle, saturé ou non / aromatique contenant N, comprenant 1-10 atomes de C dans le système cyclique. (B) représente un ou plusieurs agents herbicides choisis dans le groupe des composés 1,3-dicéto comprenant : prohexadione-calcium; trinexapac-éthyle; alloxydim; butroxydim; cléthodim; cycloxydim; profoxydim; séthoxydim; tépraloxydim; tralkoxydim; mésotrione; sulcotrione; téfuryltrione; tembotrione; 3-[[2-[(2-méthoxyéthoxy)méthyl]-6-(trifluorométhyl)pyridin-3-yl]carbonyl]bicyclo[3.2.1 ]octane-2,4-dione, cis-3-(4-chloro-2-éthoxy-6-éthylphényl)-4-hydroxy-8-méthoxy-1-azaspiro[4.5]dec-3-en-2-one, 3-(4-chloro-2-éthyl-6-méthoxyphényl)-4-hydroxy-8-méthoxy-1-azaspiro[4.5]dec-3-en-2-one et 3-(4-chloro-2-éthyl-6-méthoxyphényl)-4-hydroxy-5,5-diméthyl-1,5-dihydro-2H-pyrrol-2-one.
EP08841689A 2007-10-24 2008-10-22 Combinaison herbicide Withdrawn EP2205092A2 (fr)

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CN101902917A (zh) 2010-12-01
CL2008003143A1 (es) 2009-05-29
CA2703552A1 (fr) 2009-04-30
JP2011500743A (ja) 2011-01-06
EP2052605A1 (fr) 2009-04-29
BRPI0818895A2 (pt) 2014-10-07
AR068957A1 (es) 2009-12-16
BRPI0818895A8 (pt) 2019-01-22
AU2008315941A1 (en) 2009-04-30
WO2009053053A2 (fr) 2009-04-30
WO2009053053A3 (fr) 2010-05-20
EA201000522A1 (ru) 2010-10-29

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