Classifications

• • A—HUMAN NECESSITIES
  • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
  • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
  • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
  • A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
• • 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.
• US Pat. No. 5,476,936 discloses herbicidal active substances which combat a broad spectrum of weeds.
• these agents are sometimes not fully compatible with some important crops such as cereals. Therefore, they can not be used in some crops to ensure the desired broad herbicidal activity against harmful plants.
• the object of the present invention was to find herbicidal agents in which the selectivity of the abovementioned herbicides to important crops is increased. This object is surprisingly achieved by the herbicide-safener combination of the present invention.
• the subject of the present invention is therefore a herbicide-safener combination containing
• A is nitrogen or a CR 11 group , where R 11 is hydrogen, alkyl, halogen and haloalkyl, R 1 is hydrogen or an optionally substituted radical from the group consisting of alkyl, alkoxy, alkoxyalkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, Aralkyl and aryl, R 2 is hydrogen, halogen or each optionally halogen-substituted alkyl, alkoxy, alkylthio, alkylamino or dialkylamino each having 1 to 6 carbon atoms,
• R 3 represents hydrogen, halogen or represents in each case optionally halogen-substituted alkyl, alkoxy, alkylthio, alkylamino or dialkylamino having in each case 1 to 6 carbon atoms
• R 4 - R 7 independently of one another represent hydrogen, halogen, cyano, thiocyanato or optionally in each case Hal is substituted alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylamino, alkylcarbonyl, alkoxycarbonyl, alkylaminocarbonyl having in each case 1 to 3 carbon atoms
• R 8 is hydrogen, halogen, cyano, thiocyanato or in each case optionally halogen-substituted alkyl, alkoxy, alkylthio, Alkylsulfinyl, alkylsulfonyl, alkylamino, alkylcarbonyl
• the alkyl and alkylene groups each have 1 to 6 C atoms
• the alkenyl and alkynyl groups each have 2 to 6 C atoms
• the cycloalkyl groups in each case 3 to 6 C atoms and the aryl groups in each case 6 or 10 C May contain atoms
• the herbicide-safener combinations of the invention may contain additional additional components, e.g. B. Plant protection agents of other types and / or customary in crop 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 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), z. 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. It is also possible to use the individual active substances or the herbicide-safener combination for seed treatment.
• 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 compounds of the formula (I) and salts thereof,
• A is nitrogen or a CH group
• R 1 is hydrogen or an optionally halogen-substituted radical from the series consisting of alkyl, alkoxy, alkoxyalkyl, alkenyl and alkynyl having in each case up to 3 carbon atoms
• R 2 is hydrogen, halogen or in each case optionally halogen-substituted alkyl, alkoxy, alkylthio, alkylamino or dialkylamino having in each case 1 to 3 carbon atoms in the alkyl radicals,
• R 3 is hydrogen, halogen or in each case optionally halogen-substituted alkyl, alkoxy, alkylthio, alkylamino or dialkylamino having in each case 1 to 3 carbon atoms in the alkyl radicals,
• R 4 - R 7 independently of one another represent hydrogen, halogen, cyano, thiocyanato or in each case optionally halogen-substituted alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylamino, alkylcarbonyl, alkoxycarbonyl or alkylaminocarbonyl having in each case 1 to 3 carbon atoms in the alkyl radicals,
• R 8 represents hydrogen, halogen, cyano, thiocyanato or represents in each case optionally halogen-substituted alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylamino, alkylcarbonyl, alkoxycarbonyl or alkylaminocarbonyl having in each case 1 to 3 carbon atoms in the alkyl radicals.
• herbicide (A) is salts which are obtained from compounds of the formula (I) and bases, such as, for example, sodium, potassium or calcium hydroxide, hydride, amide and carbonate, sodium or potassium.
• bases such as, for example, sodium, potassium or calcium hydroxide, hydride, amide and carbonate, sodium or potassium.
• herbicides (A) are compounds of the formula (I) and their salts,
• A is nitrogen or a CH group
• R 1 is hydrogen, methyl, ethyl, methoxy, methoxymethyl or ethoxy
• R 2 is hydrogen, chlorine, methyl, ethyl, trifluoromethyl, methoxy, ethoxy, difluoromethoxy, methylthio, methylamino or dimethylamino
• R 3 is hydrogen, chlorine, methyl, ethyl, trifluoromethyl, methoxy, ethoxy, difluoromethoxy, methylthio, methylamino or dimethylamino
• R 4 -R 7 independently of one another are hydrogen, fluorine, chlorine, cyano, or in each case optionally substituted by chlorine or fluorine, methyl, methylthio, methylsulfinyl, methylsulfonyl, methoxycarbonyl and ethoxycarbonyl, preferably hydrogen,
• R 8 represents hydrogen, fluorine, chlorine, bromine, cyano or represents in each case optionally substituted by chlorine or fluorine methyl, methoxy, ethoxy, methylthio, ethylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl, ethylsulfonyl, methyl or dimethylamino, preferably hydrogen.
• herbicides (A) are compounds of the formula (I) and their salts, in particular their alkali metal salts,
• A is nitrogen, R 1 is hydrogen or methyl,
• R 2 is hydrogen, chlorine, methyl, ethyl, trifluoromethyl, methoxy, ethoxy, difluoromethoxy, methylthio, methylamino or dimethylamino
• R 3 is hydrogen, chlorine, methyl, ethyl, trifluoromethyl, methoxy, ethoxy, difluoromethoxy, methylthio, methylamino or dimethylamino
• R 4 - R 7 is hydrogen
• R 8 is hydrogen.
• herbicide (A) are compounds of the formula (I) and salts thereof, in particular their alkali metal salts,
• A is a CH group
• R 1 is hydrogen or methyl
• R 2 is hydrogen, chlorine, methyl, ethyl, trifluoromethyl, methoxy, ethoxy, difluoromethoxy, methylthio, methylamino or dimethylamino
• R 3 is hydrogen, chlorine, methyl, ethyl, trifluoromethyl, methoxy, ethoxy, difluoromethoxy, methylthio, methylamino or dimethylamino
• R 4 - R 7 is hydrogen
• R 8 is hydrogen.
• 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.
• salts may be optionally prepared, e.g. Metal salts such as alkali (e.g., Na, K) salts or alkaline earth (e.g., Ca, Mg) salts or ammonium or amine salts.
• alkali e.g., Na, K
• alkaline earth e.g., Ca, Mg
• Such salts are obtained in a simple manner by customary salt formation methods, for example by dissolving or dispersing a compound of formula (I) in a suitable diluent, e.g. Methylene chloride, acetone, tert-butyl methyl ether or toluene, and addition of a suitable base.
• the salts can then - be isolated by concentration or suction - optionally after prolonged stirring.
• (+) The indicated melting point (mp) refers in each case to the corresponding sodium salt, ie the corresponding compound in which the hydrogen of the -S ⁇ 2 -NH group has been replaced by sodium.
• the herbicides (A) inhibit the enzyme acetolactate synthase (ALS) and thus the protein synthesis in plants.
• the application rate of the herbicides (A) can vary with the external conditions such as temperature, humidity, the type of herbicide used in a wide range, for example between 0.001 g and 500 g AS / ha (AS / ha means hereinafter "active substance per hectare
• AS / ha means hereinafter "active substance per hectare
• the application rates are generally lower, for example in the range from 0.001 g to 100 g AS / ha, preferably 0.005 g to 50 g AS / ha, more preferably 0.01 g to 9 g AS / ha.
• the herbicides (A) are suitable for controlling harmful plants, for example in crops, for example in economically important arable crops such as monocotyledonous crops such as cereals (eg wheat, barley, rye, oats), rice, corn, millet or dicotyledonous crops such as sugar beet, oilseed rape , Cotton, sunflower and legumes, eg of the genera Glycine (eg Glycine max. (Soya) as non-transgenic Glycine max. (Eg conventional varieties such as STS varieties) or transgenic Glycine max.
• crops for example in economically important arable crops such as monocotyledonous crops such as cereals (eg wheat, barley, rye, oats), rice, corn, millet or dicotyledonous crops such as sugar beet, oilseed rape , Cotton, sunflower and legumes, eg of the genera Glycine (eg Glycine max. (Soya) as non-transgenic Glycine max. (
• the herbicide-safener combinations (A) + (B) are also useful in tolerant and non-tolerant mutant cultures and tolerant and intolerant transgenic cultures, preferably of corn, rice, corn, oilseed rape and soy, for example, those directed against imidazolinone herbicides. Atrazine, glufosinate or glyphosate are resistant.
• 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.
• the safeners (B) are preferably selected from the group consisting of: a) compounds of the formulas (II) to (IV),
• n ' is a natural number from 0 to 5, preferably 0 to 3
• T is a (Ci or C2) 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
• W is an unsubstituted or substituted divalent heterocyclic radical from the group of unsaturated or unsaturated five-membered ring heterocycles having 1 to 3 hetero ring N or O atoms, at least one N atom and at most one O atom in the ring, preferably a radical from the group (W1) to (W4),
• R 17 , R 19 are identical or different halogen, (-CC 4 ) alkyl, (-CC 4 ) alkoxy, nitro or (dC 4 ) haloalkyl;
• R 18 , R 20 are identical or different OR 24 , SR 24 or NR 24 R 25 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 (II) or (III) and unsubstituted or substituted by radicals from the group (-CC 4 ) alkyl, (-CC 4 ) alkoxy or optionally substituted phenyl , preferably a radical of the formula OR 24 , NHR 25 or N (CH 3 ) 2 , in particular of the formula OR 24 ;
• R 24 is hydrogen or an unsubstituted or substituted aliphatic hydrocarbon radical, preferably having a total of 1 to 18 C atoms;
• R 25 is hydrogen, (C ⁇ -C6) alkyl, (C 1 -C 6) alkoxy or substituted or unsubstituted phenyl;
• R x is H, (C 1 -C 8 ) alkyl, CC 8 (haloalkyl), (C 1 -C 4 ) alkoxy (C 1 -C 8 ) alkyl, cyano or COOR 26 , wherein R 2 ⁇ is hydrogen, (C 1 -C 8 ) alkyl, (C ⁇ -C8) haloalkyl, (dC 4) AIkoxy- (C ⁇ -C4) alk l, (dC 6) hydroxyalkyl, (C 3 -C 12) cycloalkyl or tri (C ⁇ -C4) alkyl -silyl is; R 27 , R 28 , R 29 are identical or different hydrogen, (-CC ⁇ ) alkyl, (-CC 8 ) haloalkyl, (C 3 -C 2 ) cycloalkyl or substituted or unsubstituted phenyl;
• R 21 is (dC 4) alkyl, (dC 4) haloalkyl, (C 2 -C 4) alkenyl, (C 2 -C 4) haloalkenyl, (C 3 -C) cycloalkyl, preferably dichloromethyl;
• R 22, R 23 is identical or different hydrogen, (dC 4) alkyl, (C 2 -C 4) alkenyl, (C 2 -C 4) alkynyl, (C ⁇ -C4) haloalkyl, (C 2 -C 4) haloalkenyl, (dC 4) alkylcarbamoyl (C ⁇ -C4) alkyl, (C 2 -C 4) Alkenylcarbamoyl- (C 1 -C 4) alkyl, (C -C 4) alkoxy (C 1 -C 4) alkyl , Dioxolanyl- (C 1 -C 4 ) alkyl, thiazoly
• R 30 is hydrogen, a hydrocarbon radical, a hydrocarbonoxy radical, a hydrocarbylthio radical or a heterocyclyl radical which is preferably bonded via a carbon atom, where each of the last-mentioned 4 radicals is unsubstituted or substituted by one or more identical or different radicals from the group halogen, cyano, nitro , Amino, hydroxy, carboxy, formyl, carbonamide, sulfonamide and radicals of the formula -Z a -R a is substituted, wherein each hydrocarbon moiety preferably 1 to 20 carbon atoms and a C-containing radical R 30 including substituents preferably 1 to 30 Having C atoms;
• R 31 is hydrogen or (-CC) alkyl, preferably hydrogen, or R 30 and R 31 together with the group of the formula -CO-N- the radical of a 3- to 8-membered saturated or unsaturated ring;
• R 32 is identical or different and is halogen, cyano, nitro, amino, hydroxyl, carboxy, formyl, CONH 2 , SO 2 NH 2 or a radical of the formula -Z b -R b
• R, 33 is hydrogen or (C 1 -C 4 ) -alkyl, preferably H;
• R 34 is identical or different and is halogen, cyano, nitro, amino, hydroxyl, carboxy, CHO, CONH 2 , SO 2 NH 2 or a radical of the formula -Z c -R c ;
• R a is a hydrocarbon radical or a heterocyclyl radical, where each of the latter two radicals is unsubstituted or substituted by one or more identical or different radicals from the group of halogen, cyano, nitro, amino, hydroxyl, mono- and di- [(C 1 -C 4 ) - alkyl] -amino, or an alkyl radical in which several, preferably 2 or 3, non-adjacent CH 2 groups are each replaced by an oxygen atom;
• R b , R c identically or differently, are a hydrocarbon radical or a heterocyclyl radical, where each of the two last-menti
• Z a is a divalent group of the formula -O-, -S-, -CO-, -CS-, -CO-O-, -CO-S-, -O-CO-, -S-CO-, -SO- , -SO 2 -, -NR * -, -CO-NR * -, -NR * -CO-, -SO 2 -NR * - or -NR * -S ⁇ 2 -, wherein the binding on the right of the respective divalent group the bond to the radical R a and wherein R independently in the 5 last-mentioned radicals in each case, (dC 4) -alkyl or halo- (dC 4) * one another are H - alkyl;
• Z b , Z c independently of one another a direct bond or a divalent group of the formula -O-, -S-, -CO-, -CS-, -CO-O-, -CO-S-, -O-CO-, -S-CO-, -SO-, -SO 2 -, -NR * -, -SO 2 -NR * -, -NR * -SO 2 -, -CO-NR * - or -NR * -CO-, where the bond on the right of the respective divalent group is the bond to the radical R b or R ° and where the R * in the last-mentioned 5 radicals are each independently H, (-CC 4 ) -alkyl or halo- (dC 4 ) -alkyl; n is an integer from 0 to 4, preferably 0, 1 or 2, in particular 0 or 1, and m is an integer from 0 to 5, preferably 0, 1, 2 or 3, in particular 0, 1 or 2; mean
• X 3 is CH or N
• R 35 Hydrogen, heterocyclyl or a hydrocarbon radical, where the latter two radicals are optionally substituted by one or more, identical or different radicals from the group halogen, cyano, nitro, amino, hydroxyl, carboxy, CHO, CONH 2 , SO 2 NH 2 and Z a - R a are substituted;
• R 36 is hydrogen, hydroxy, (dC 6) alkyl, (C 2 -C 6) alkenyl, (C 2 -C 6) -alkynyl, (dC 6) - alkoxy, (C 2 -C 6) alkenyloxy, wherein the five last-mentioned radicals optionally substituted by one or more identical or different radicals from the group halogen, hydroxy, (C ⁇ -C4) alkyl, (dC 4) -alkoxy and (C ⁇ -C 4) - substituted alkylthio, or R 35 and R 36 together with the nitrogen atom carrying them have a 3- to 8-member
• R 39 is halogen, cyano, nitro, amino, hydroxy, carboxy, phosphoryl, CHO, CONH 2 , SO 2 NH 2 or Z c -R c ;
• R a is a (C 2 -C 20) -alkyl radical whose carbon chain is interrupted one or more times by oxygen atoms, heterocyclyl or a hydrocarbon radical, where the latter two radicals are optionally substituted by one or more, identical or different radicals from the group halogen, cyano , Nitro, amino, hydroxy, mono- and di- [(C 1 -C 4 ) -alkyl] -amino;
• R b , R c identically or differently, denote a (d-dc-alkyl radical whose carbon chain is interrupted one or more times by oxygen atoms, heterocyclyl or a hydrocarbon radical, where the latter two radicals optionally substituted by one or more, identical or different radicals from the group halogen, cyano, nitro, amino, hydroxy, phosphoryl, (CC 4 ) - haloalkoxy, mono- and di - [(dC 4 ) -alkyr] -annino;
• Z a is a divalent unit selected from O, S, CO, CS, C (O) O, C (O) S, SO, SO 2 , NR d , C (O) NR d or SO 2 NR d ;
• Z b , Z c identically or differently, denote a direct bond or a divalent unit from the group O, S, CO, CS, C (O) O, C (O) S, SO, SO 2 , NR d , SO 2 NR d or C (O) NR d ;
• R d is hydrogen, (C 1 -C 4 ) -alkyl or (C 1 -C 4 ) -haloalkyl; n is an integer from 0 to 4, and in the case where X is CH, an integer of 0 to 5, and in the case where X is N, an integer of 0 to 4;
• R ⁇ and R ⁇ independently of one another are hydrogen, C 1 -C 8 -alkyl, C 3 -C 8 -cycloalkyl, C 3 -C 6 -alkenyl, C 3 -C 6 -alkynyl, or by C 4 -alkoxy or
• R ⁇ and R ß together are a C 4 -C 6 alkylene or by oxygen, sulfur, SO, SO 2, NH or -N (dC 4 alkyl) - interrupted C 4 -C 6 - alkylene bridge,
• R ⁇ is hydrogen or C 1 -C 4 -alkyl
• R a and R b independently of one another represent hydrogen, halogen, cyano, nitro, trifluoromethyl, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -alkylthio, dd-alkylsulfinyl, C 1 -C 4 -alkylsulfonyl, -COOR j -CONR k R m , -COR n , -SO 2 NR k R m or -OSO 2 -C !
• Halogen or dd-alkyl may be substituted, or a C 3 -C 4 - alkenylene, which may be substituted by halogen or -CC 4 alkyl, or a C 4 -Alkadienylen Kunststoff substituted by halogen or Ci-d-alkyl and R 9 and R h independently of one another represent hydrogen, halogen, dd-alkyl, trifluoromethyl, methoxy, methylthio or -COOR j , where R c is hydrogen, halogen, C 1 -C 4 -alkyl or methoxy, R d is hydrogen, halogen, Nitro, dd-alkyl, C 1 -C 4 -alkoxy, dd-alkylthio, C 1 -C 4 -alkylsulfinyl, C 1 -C 4 -al
• R k and R m together denote a dd-alkylene bridge or a through oxygen, NH or -N (-C-alkyl) - interrupted dC 6 alkylene, and R n is dd-alkyl, phenyl or by halogen, dd-alkyl, methoxy Mean phenyl substituted with nitro or trifluoromethyl
• herbicidally effective amount means an amount of one or more herbicides which is suitable for negatively influencing plant growth.
• Antidote effective amount in the context of the invention means an amount of one or more safeners, which is suitable to reduce the phytotoxic effect of crop protection agents (eg of herbicides) on crop plants.
• radicals alkyl, alkoxy, haloalkyl, haloalkoxy, alkylamino and alkylthio and the corresponding unsaturated and / or substituted radicals can each be straight-chain or branched in the carbon skeleton.
• Alkyl radicals also in the compound meanings such as alkoxy, haloalkyl, etc., preferably have 1 to 4 C atoms and, for example. Methyl, ethyl, n- or i-propyl, n-, i-, t- or 2-butyl.
• Alkenyl and alkynyl radicals have the meaning of the possible unsaturated radicals corresponding to the alkyl radicals; Alkenyl means e.g.
• Alkynyl means e.g. Propargyl, but-2-yn-1-yl, but-3-yn-1-yl, 1-methyl-but-3-yn-1-yl.
• (d-d) -Alkyr is the shorthand notation for alkyl of 1 to 4 carbon atoms, as well as other general definitions of radicals with bracketed ranges for the possible number of carbon atoms.
• Cycloalkyl is preferably a cyclic alkyl radical having 3 to 8, preferably 3 to 7, particularly preferably 3 to 6, C atoms, for example cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl.
• Cycloalkenyl and cycloalkynyl refer to corresponding unsaturated compounds.
• Halogen is fluorine, chlorine, bromine or iodine.
• Haloalkyl, haloalkenyl and haloalkynyl by halogen preferably by fluorine, chlorine and / or bromine, in particular by fluorine or chlorine, partially or completely substituted alkyl, alkenyl or alkynyl, for example CF 3 , CHF 2 , CH 2 F, CF 2 CF 3 ) CH 2 CHFCl, CCI 3 , CHCl 2 , CH 2 CH 2 Cl.
• Haloalkoxy is eg OCF 3 , OCHF 2) OCH 2 F, OCF 2 CF 3 , OCH 2 CF 3 and OCH 2 CH 2 Cl. The same applies to other halogen-substituted radicals.
• a hydrocarbon radical may be an aromatic or an aliphatic hydrocarbon radical, where an aliphatic hydrocarbon radical is generally a straight-chain or branched saturated or unsaturated radical
• Hydrocarbon radical is, preferably with 1 to 18, particularly preferably 1 to 12 C-atoms, e.g. Alkyl, alkenyl or alkynyl.
• aliphatic hydrocarbon radical alkyl, alkenyl or alkynyl having up to 12 carbon atoms Preferably, aliphatic hydrocarbon radical alkyl, alkenyl or alkynyl having up to 12 carbon atoms; the same applies to an aliphatic hydrocarbon radical in a Kohlenwasserstoffoxyrest.
• Aryl is generally a mono-, bi- or polycyclic aromatic system having preferably 6-20 C atoms, preferably 6 to 14 C atoms, more preferably 6 to 10 C atoms, e.g. Phenyl, naphthyl, tetrahydronaphthyl, indenyl, indanyl, pentalenyl and fluorenyl, more preferably phenyl.
• Heterocyclic ring, heterocyclic radical or heterocyclyl means a mono-, bi- or polycyclic ring system which is saturated, unsaturated and / or aromatic and contains one or more, preferably 1 to 4, heteroatoms, preferably from the group N, S and O. ,
• saturated heterocycles having 3 to 7 ring atoms and one or two heteroatoms from the group N, O and S, wherein the chalcogens are not adjacent.
• Particularly preferred are monocyclic rings having 3 to 7 ring atoms and a heteroatom from the group N, O and S, and morpholine, dioxolane, piperazine, imidazoline and oxazolidine.
• Very particularly preferred saturated heterocycles are oxirane, pyrrolidone, morpholine and tetrahydrofuran.
• partially unsaturated heterocycles having 5 to 7 ring atoms and one or two heteroatoms from the group N, O and S.
• Particularly preferred are partially unsaturated heterocycles having 5 to 6 ring atoms and one heteroatom from the group N, O and S.
• Very particular preferred partially unsaturated heterocycles are pyrazoline, imidazoline and isoxazoline.
• heteroaryl e.g. mono- or bicyclic aromatic heterocycles having 5 to 6 ring atoms containing one to four heteroatoms from the group N, O, S, wherein the chalcogens are not adjacent.
• monocyclic aromatic heterocycles having 5 to 6 ring atoms which contain a heteroatom from the group, N, O and S, and pyrimidine, pyrazine, pyridazine, oxazole, thiazole, thiadiazole, oxadiazole, pyrazole, triazole and isoxazole.
• pyrazole, thiazole, triazole and furan is particularly preference is given to pyrazole, thiazole, triazole and furan.
• Substituted radicals such as substituted hydrocarbon radicals, for example substituted alkyl, alkenyl, alkynyl, aryl, such as phenyl and arylalkyl, such as benzyl, or substituted heterocyclyl, represent a substituted radical derived from the unsubstituted radical, where the substituents are preferably one or more, preferably 1, 2 or 3 , in the case of Cl and F also up to the maximum possible number, substituents from the group halogen, alkoxy, haloalkoxy, alkylthio, hydroxy, amino, nitro, carboxy, cyano, azido, alkoxycarbonyl, alkylcarbonyl, formyl, carbamoyl, mono- and dialkylaminocarbonyl , substituted amino such as acylamino, mono- and dialkylamino and alkylsulfinyl, haloalkylsulfinyl, alkylsulfon
• Preferred substituents from the group are preferably halogen from the group halogen, for example fluorine or chlorine, (dC) alkyl, preferably methyl or ethyl, (-C-d) haloalkyl, preferably trifluoromethyl, (-C-d) alkoxy, preferably methoxy or ethoxy, (C ⁇ -d) haloalkoxy, nitro and Cyano. Particularly preferred are the substituents methyl, methoxy and chlorine.
• Mono- or disubstituted amino means a chemically stable radical from the group of substituted amino radicals which are N-substituted by, for example, one or two identical or different radicals from the group consisting of alkyl, alkoxy, acyl and aryl; preferably monoalkylamino, dialkylamino, acylamino, arylamino, N-alkyl-N-arylamino and N-heterocycles.
• alkyl radicals having 1 to 4 carbon atoms are preferred.
• Aryl is preferably phenyl.
• Substituted aryl is preferably substituted phenyl.
• acyl the definition given below applies, preferably (-CC) alkanoyl. The same applies to substituted hydroxylamino or hydrazino.
• Optionally substituted phenyl is preferably phenyl which is unsubstituted or mono- or polysubstituted, preferably up to three times, in halogens such as Cl and F also up to five times, by identical or different radicals from the group
• Halogen for example o-, m- and p-tolyl, dimethylphenyls, 2, 3 and 3 4-chlorophenyl, 2-, 3- and 4-trifluoro and trichlorophenyl, 2,4-, 3,5-, 2,5- and 2,3-dichlorophenyl, o-, m- and p-methoxyphenyl.
• An acyl group means the residue of an organic acid preferably having up to 6 C atoms, e.g. the radical of a carboxylic acid and radicals derived therefrom, such as the thiocarboxylic acid, optionally N-substituted iminocarboxylic acids, or the radical of carbonic acid monoesters, optionally N-substituted carbamic acids, sulfonic acids, sulfinic acids, phosphonic acids, phosphinic acids.
• Acyl is, for example, formyl, alkylcarbonyl, such as (C 1-6 -alkyl) carbonyl, phenylcarbonyl, where the phenyl ring may be substituted, e.g.
• phenyl or alkyloxycarbonyl, phenyloxycarbonyl, benzyloxycarbonyl, alkylsulfonyl, alkylsulfinyl or N-alkyl-1-iminoalkyl.
• stereoisomers which have the same topological linkage of the atoms, and mixtures thereof.
• Such compounds contain one or more asymmetric C atoms or double bonds, which are not specified separately in the general formulas.
• the possible defined by their specific spatial form possible stereoisomers, such as enantiomers, diastereomers, Z and E isomers can be obtained by conventional methods from mixtures of stereoisomers or prepared by stereoselective reactions in combination with the use of stereochemically pure starting materials.
• the compounds of formula (II) are e.g. from EP-A-0 333 131 (ZA-89/1960), EP-A-0 269 806 (US-A-4,891,057), EP-A-0 346 620 (AU-A-89/34951), EP-A-0 174 562, EP-A-0 346 620 (WO-A-91/08 202), WO-A-91/07 874 or WO-A 95/07 897 (ZA 94/7120) and the There cited literature known or can be prepared by or analogous to the method described therein.
• EP-A-0 086 750 discloses the compounds of formula (III) in EP-A-0 086 750, EP-A-0 94349 (US-A-4,902,340), EP-A-0 191736 (US-A-4,881,966) and EP-A No. 0492 366 and literature cited therein or can be prepared by or analogously to the processes described therein. Some compounds are further described in EP-A-0 582 198 and WO 2002/34048.
• Group B (b) compounds are further described in CN-A-87 / 102,789, EP-A-365484 and The Pesticide Manual, The British Crop Protection Council and the Royal Society of Chemistry, 11th edition, Farnham 1997, known.
• group B (c) The compounds of group B (c) are described in WO-A-97/45016, those of group B (d) in WO-A-99/16744 and those of group B (e) in EP-A-365484 described.
• R 24 is hydrogen, (C 1 -C 4) -alkyl, (C 3 -C 12 ) ) -Cycloalkyl, (C 2 -C 8 ) -alkenyl and (C 2 -C ⁇ 8 ) alkynyl, where the C-containing groups may be substituted by one or more, preferably up to three, radicals R 50 ;
• R 50 is identical or different halogen, hydroxy, (C ⁇ -C8) alkoxy, (CC 8) alkylthio, (C 2 -C 8) alkenylthio, (C 2 -C 8) alkynylthio, (C 2 -C 8) Alkenyloxy, (C 2 -C 8 ) alkynyloxy, (C 3 -C) cycloalkyl, (C 3 -C)
• R 52 is identical or different halogen, (C ⁇ -d) alkyl, (C ⁇ -C 4) alkoxy, (dC 4) haloalkyl, (dC 4) -haloalkoxy or nitro;
• R ' is the same or different hydrogen, (C 1 -C 4 ) alkyl, phenyl which is unsubstituted or substituted by one or more, preferably up to three, radicals R 52 or two radicals R' together form a (C 2 -C 6 ) alkanediyl chain;
• R is identical or different (C 1 -C) alkyl or two radicals R" together form a (C 2 -C 6 ) alkanediyl chain;
• R '" is hydrogen or (C 1 -C 4 ) alkyl; m is 0, 1, 2, 3, 4, 5 or 6.
• herbicide-safener combinations according to the invention containing safeners of the formula (II) and / or (III) in which the symbols and indices have the following meanings:
• R 24 is hydrogen, (-CC 8 ) alkyl or (C 3 -C 7 ) -cycloalkyl, where the above C-containing radicals are unsubstituted or mono- or polysubstituted by halogen or one or two times, preferably simply, by radicals R 50 are substituted,
• R 17 , R 19 are identical or different halogen, methyl, ethyl, methoxy, ethoxy, (d or dJ-haloalkyl, preferably hydrogen, halogen or (Ci or C 2 ) - haloalkyl.
• R 24 is hydrogen, (-CC 8 ) alkyl or (C 3 -C 7 ) cycloalkyl, where the above C-containing radicals are unsubstituted or mono- or polysubstituted, preferably up to three times, by identical or different halogen radicals or up to two times, preferably monosubstituted, by identical or different radicals from the group hydroxy, (C ⁇ -C) alkoxy, (C ⁇ -d) alkoxycarbonyl, (C 2 - C 6) alkenyloxycarbonyl, (C 2 -C 6) alkynyloxycarbonyl, 1 - (hydroxyimino) - (C ⁇ -C 4) - alkyl, 1 - [(dC 4) alkylimino] - (C ⁇ -C 4) alkyl, 1 - [(dC 4) alkoxyimino] - (C ⁇ -C 4) - alkyl and radicals of the formulas -SiR '
• R 19 is halogen or (dC 4 ) haloalkyl; n 'is 0, 1, 2 or 3, wherein (R 19 ), y is preferably 5-Cl;
• R 20 is a group of formula OR 24 ;
• T is CH 2 or CH (COO- (dC 3 alkyl))
• R 24 is hydrogen peroxide ((CC ⁇ - CC 88 )) AAlkkyyl ,, ((dd - CC 88 )) H-haloalkyl or (C 1 -C 4) alkoxy- (C 1 -C 4) -alkyl, preferably hydrogen or (C 1 -C 8) C 8 ) alkyl.
• R 17 is halo or (dC 2 ) haloalkyl; n 'is 0, 1, 2 or 3, wherein (R 17 ) n ' is preferably 2,4-CI 2 ; R 18 is a radical of the formula OR 24 ;
• R 24 is hydrogen, (C ⁇ -C8) alkyl, (dC 4) haloalkyl, (C ⁇ -C 4) hydroxyalkyl, (C 3 - C 7) cycloalkyl, (C 1 -C 4) alkoxy- (C 1 -C 4) -alkyl or tri- (C 1 -C 2) -alkylsilyl, preferably (C ⁇ -C 4) alkyl;
• R 27 is hydrogen, (C 1 -C 8 ) alkyl, (CC 4 ) haloalkyl or (C 3 -C 7 ) cycloalkyl, preferably hydrogen or (C 1 -C 4 ) alkyl, and
• R x is COOR 26 wherein R 26 is hydrogen, (DC 8) alkyl, (dC 4) haloalkyl, (dC 4) hydroxyalkyl, (C 3 -C 7) cycloalkyl, (C 1 -C 4) alkoxy- ( C 1 -C 4 ) -alkyl or tri (C 1 -C 2 ) -alkylsilyl, preferably hydrogen or (-CC) alkyl.
• herbicidal compositions containing a safener are also particularly preferred.
• W (W2)
• R 17 is halo or (dC 2 ) haloalkyl; n 'is 0, 1, 2 or 3, wherein (R 17 ) n ' is preferably 2,4-CI 2 ; R 18 is a radical of the formula OR 24 ; R 24 is hydrogen, (DC 8) alkyl, (C ⁇ -C) haloalkyl, (dC 4) hydroxyalkyl, (C 3 -C 7) cycloalkyl, (C ⁇ -C 4 alkoxy) -CC 4 alkyl or tri ( dC 2 ) -alkyl-silyl, preferably (-C-d) alkyl, and
• R 27 is hydrogen, (DC 8) alkyl, (C ⁇ -C4) haloalkyl, (C 3 -C 7) cycloalkyl or unsubstituted or substituted phenyl, preferably hydrogen, (d-d) alkyl or phenyl which is unsubstituted or substituted by a or a plurality of radicals from the group halogen, (-CC 4 ) alkyl, (-CC) haloalkyl, nitro, cyano or (-C-d) alkoxy is substituted.
• W (W3)
• R 17 is halo or (dC 2 ) haloalkyl; n 'is 0, 1, 2 or 3, wherein (R 17 ) n ' is preferably 2,4-CI 2 ; R 18 is a radical of the formula OR 24 ;
• R 24 is hydrogen, (CC 8 ) alkyl, (dC 4 ) haloalkyl, (dC 4 ) hydroxyalkyl, (C 3 -C 7 ) cycloalkyl, (C 1 -C 4 ) alkoxy (C 1 -C 4 ) alkyl or tri (dC 2 ) -alkylsilyl, preferably (-CC) alkyl, and
• R 28 is (C 8 -C 8 ) alkyl or (dd) haloalkyl, preferably C 1 -C 6 haloalkyl.
• W (W4)
• R 17 is halogen, nitro, (-CC) alkyl, (dC 2 ) haloalkyl, preferably CF 3 , or (-CC 4 ) alkoxy; n 'is 0, 1, 2 or 3; m 'is 0 or 1;
• R 18 is a radical of the formula OR 24 ;
• R 24 is hydrogen, (C 1 -C 4 ) alkyl, carboxy (C 1 -C 4 ) -alkyl, (C 1 -C 4 ) alkoxycarbonyl (CC 4 ) -alkyl, preferably (C 1 -C 4 ) alkoxy-CO-CH 2 - l (dC 4 ) alkoxy-CO-C (CH 3 ) H, HO-CO-CH 2 - or HO-CO-C (CH 3 ) H-, and R 29 is hydrogen, (dd) alkyl, (dC 4 ) haloalkyl, (C 3 -C 7 ) cycloalkyl or phenyl which is unsubstituted or substituted by one or more of halogen, (dC 4 ) alkyl, (dC 4 ) Haloalkyl, nitro, cyano and (dC 4 ) alkoxy.
• Dichloroacetamide type compounds i. of the formula (IV), preferably: N, N-diallyl-2,2-dichloroacetamide (dichloromide (IV-1), from US Pat. No. 4,137,070), 4-dichloroacetyl-3,4-dihydro-3-methyl-2H- 1, 4-benzoxazine (IV-2, Benoxacor, from EP 0 149 974), N1, N2-diallyl-N2-dichloroacetylglycine amide (DKA-24 (IV-3), from HU 2143821), 4-dichloroacetyl-1 oxa-4-aza-spiro [4,5] decane (AD-67), 2,2-dichloro-N- (1, 3-dioxolan-2-ylmethyl) -N- (2-propenyl) acetamide (PPG) 1292), 3-dichloroacetyl-2,2,5-trimethyloxazolidine (R-
• h) compounds of group B preferably 1,8-naphthalic anhydride (b-1), methyl-diphenylmethoxyacetate (b-2), cyanomethoxyimino (phenyl) acetonitrile (cyometrinil) (b-3), 1- (2- Chlorobenzyl) -3- (1-methyl-1-phenylethyl) urea (cumyluron) (b-4), O, O-diethyl S-2-ethylthioethyl phosphorodithioate (disulfonone) (b-5), 4-chlorophenyl methylcarbamate ( Mephenate) (b-6), O, O-diethyl-O-phenyl phosphorotioate (dietholate) (b-7), 4-carboxy-3,4-dihydro-2H-1-benzopyran-4-acetic acid (CL-304415, CAS Regno: 31541-57-8) (b-8), 1, 3-diox
• R 30 is hydrogen, (C 1 -C 6 ) -alkyl, (C 3 -C 6 ) -cycloalkyl, furanyl or thienyl, where each of the last-mentioned 4 radicals is unsubstituted or substituted by one or more substituents from the group consisting of halogen, (C 1 -C 4) -alkoxy , Halo (C 1 -C 6) -alkoxy and (C 1 -C) -alkylthio and in the case of cyclic radicals also (dd) -alkyl and (C 1 -C 4 ) -haloalkyl, R 31 is hydrogen, (C 1 -C 6 ) -alkyl, (C 3 -C 6 ) -cycloalkyl, furanyl or thienyl, where each of the last-mentioned 4 radicals is unsubstituted or substituted by one or more substituents from the group consisting of
• R 32 is halogen, halo (C 1 -C 4) alkyl, halo (C ⁇ -C 4) -alkoxy, (C ⁇ -C4) alkyl, (C ⁇ -C4) alkoxy, (dC 4) - Alkylsulfonyl, (dd) -alkoxycarbonyl or (dd) -alkylcarbonyl, preferably halogen, (dC 4 ) -halogena!
• Kyl such as trifluoromethyl, (Ci-d) - alkoxy, halogeno (CC 4 ) -alkoxy, (C -C 4) -alkoxycarbonyl or (C 1 -C 4) - alkylsulfonyl, R 33 is hydrogen,
• R 34 is halogen, (C 1 -C 4 ) -alkyl, halogeno (CC 4 ) -alkyl, halogeno (CC 4 ) -alkoxy, (C 3 -C 6 ) -cycloalkyl, phenyl, (C 1 -C 4 ) -alkoxy, cyano, (C 1 -C 4 ) -Alkylthio, (dC 4 ) - Alkylsulfinyl, (C 1 -C 4 ) -alkylsulfonyl, (C 1 -C 4 ) -alkoxycarbonyl or (C 1 -C 4 ) -alkylcarbonyl, preferably halogen, (C 1 -C 4 ) -alkyl, (C 1 -C 4 ) -haloalkyl, such as trifluoromethyl, halogeno (C 1 -C 4 ) -alkoxy, (C 1
• R 35 is hydrogen, (C 1 -C 6 ) -alkyl, (C 3 -C 6 ) -cycloalkyl, (C 2 -C 6 ) -alkenyl, (C 5 -C 6 ) -cycloalkenyl, phenyl or 3 to 6-membered heterocyclyl with up to three heteroatoms from the group consisting of nitrogen, oxygen and sulfur, where the six last-mentioned radicals are optionally substituted by one or more identical or different substituents from the group consisting of halogen, (Ci-d) -alkoxy, (dC 6 ) -haloalkoxy, ( d-dJ-alkylsulfinyl, (C 1 -C 2 ) -alkylsulfonyl, (C 3 -C 6 ) -cycloalkyl, (C 1 -C 4 ) -alkoxycarbonyl, (C 1 -C 4 ) -alkyl
• Preferred safeners of formula (VII) are (S3-1), (S3-2), (S3-3), (S3-4) and (S3-5).
• Particularly preferred safeners are dymron (b-14), fenclorim (b-11), cumyluron (b-4), isoxadifen-ethyl (II-9), mefenpyr-diethyl (11-1), cloquintocet-mexyl (111-1 ), S3-1, h-1, h-2, h-3, dietholates (b-7), disulfonone (b-5), 1, 8, naphthalic anhydride (b-1), fluxofenim (b-1o), Dichloromide (IV-1), Benoxacor (IV-2), Flurazole (b-12), R-29148 (IV-4).
• Particularly preferred for use in rice are dymron, fenclorim, cumyluron, isoxadifen-ethyl.
• Particularly preferred for use in cereals are mefenpyr-diethyl, cloquintocet-mexyl, in corn, in particular isoxadifen-ethyl, (S3-1), (h-1), (h-2), (h-3), 1, 8 , Naphthalic anhydride, Fluxofenim, Dichlormid, Benoxacor, Flurazole and R-29148.
• Isoxadifen-ethyl is preferred for use in sugar cane.
• Examples of preferred combinations of herbicidal active compounds (A) and safeners (B) are: (1-1) + (II-O), (1-1) + (11-1), (1-1) + (H-) 2), (1-1) + (II-3), (1-1) + (II-4), (1-1) + (II-5), (1-1) + (II-6) , (1-1) + (II-9), (1-1) + (11-12), (1-1) + (111-1), (1-1) + (III-4), ( 1-1) + (111-10), (1-1) + (111-1 1), (1-1) + (IV-1), (1-1) + (IV-2), (1 -1) + (IV-3), (1-1) + (IV-4), (1-1) + (IV-5), (1-1) + (b-1), (1-1 ) + (b-2), (1-1) + (b-3), (1-1) + (b-4), (1-1) + (b-5), (1-1) + (b-6), (1-1) + (b-7), (1-1) + (b-8), (1-1) + (b-9), (1
• the safeners (antidotes) of the formulas (II) - (VIII) and the compounds of group (B) (b), for example safeners of the preferred groups a) to h), are suitable for the reduction of phytotoxic effects which occur when herbicides ( A) can occur in crops without significantly affecting the efficacy of these herbicidal active substances against harmful plants.
• the field of application of conventional crop protection agents can be considerably extended, for example, to crops in which hitherto the use of the herbicides was 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 0.001 to 5 kg, preferably 0.005 to 2.5 kg of active ingredient per hectare.
• the herbicidal active ingredients (A) and the safeners (B) may be applied together (e.g., as a final formulation or in the tank-mix process) or in any order sequentially, e.g. 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 from 1: 1000 to 1000: 1.
• the optimum amounts of herbicide and safener depend on the type of herbicide and safener used and on the type and stage of development of the plant stock to be treated, and can be determined on a case-by-case basis by simple, routine preliminary tests.
• 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 seed eg grains, seeds or vegetative propagules such as tubers or sprouts with buds
• seedlings with the safeners (B) optionally in combination with other agrochemical active ingredients pretreated.
• the active ingredients can be added to the seed by pickling or the active substances and the seed can be added to water or other solvents, and the active compounds can be absorbed, 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).
• the seed or seedling treatment can be carried out with the safeners (B) alone or together with other agrochemical active substances - such as herbicides, in particular the herbicides (A), fungicides, insecticides or agents for plant strengthening, fertilization or for accelerating the swelling and germination processes.
• the safeners can then be applied again before, after or together with the herbicides (A) after the pretreatment application. By 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 shoot parts with buds) or the area on which the plants grow (eg the cultivated area), 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 shoot parts with buds
• the area on which the plants grow eg the cultivated area
• one or more safeners (B) preferably one or more, in particular one, compound of formula (II), (III), (IV), (V), (VI), (VII), (VIII), and / or from the group B (b) before, after or simultaneously with the herbicide or herbicides (A) on the plants, the seed or the area on which the plants grow (eg the acreage) are applied.
• the safeners (B) are used for seed treatment.
• Undesirable plants are understood to mean all plants that grow in places where they are undesirable.
• harmful plants for example monocotyledonous or dicotyledonous weeds or undesired crop plants
• harmful plants for example monocotyledonous or dicotyledonous weeds or undesired crop plants
• certain herbicidal active substances such as glyphosate, atrazine, glufosinate or imidazolinone herbicides.
• Monocotyledonous weeds are derived e.g. the genera Echinochloa, Setaria, Panicum, Digitaria, Phleum, Poa, Festuca, Eleusine, Brachiaria, Lolium, Bromus, Avena, Cyperus, Sorghum, Agropyron, Cynodon, Monochoria, Fimbristylis, Sagittaria, Eleocharis, Scirpus, Paspalum, Ishaemum, Sphenoclea, Dactyloctenium, Agrostis, Alopecurus, Apera. Dicotyledonous weeds are derived e.g.
• 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. (eg conventional varieties such as STS varieties) or transgenic glycines 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 and stone fruit, berry fruit, wine, Hevea, bananas, sugar cane, coffee, tea, citrus, nut orchards, turf, palm tree crops and forest crops.
• 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 herbicide-safener combinations of the invention may be prepared by known methods, e.g. be prepared as mixed formulations of the individual components, optionally with 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 individual 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 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.
• the application of the combinations according to the invention in economically important transgenic crops of useful and ornamental plants, eg. Cereals (e.g., wheat, barley, rye, oats), millet, rice, cassava, and corn, or also sugar beet, cotton, soy, 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, under Pressurized liquefied gases and / or solid carriers, optionally with the use of surfactants, ie emulsifiers and / or dispersants and / or foam-forming agents.
• extenders ie liquid solvents
• surfactants 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.
• 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-shaped polymers, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, and natural Phospholipids such as cephalins and lecithins and synthetic phospholipids.
• Other additives may be mineral and vegetable oils.
• Dyes such as inorganic pigments, e.g. Iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin, azo and metal phthalocyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.
• inorganic pigments e.g. Iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin, azo and metal phthalocyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.
• the formulations generally contain between 0.1 and 95 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 application is the joint application of 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.
• a common formulation of the combination of active ingredients (A) and (B) according to the invention has the advantage of easier applicability because the quantities of the components can already be adjusted in the optimum ratio to each other.
• the adjuvants in the formulation can be optimally matched to one another.
• agrochemical active substances such as herbicides, fungicides or insecticides, as described, for example, in Weed Research 26, 441-445 (1986) or "The Pesticide Manual , 13th edition, The British Crop Protection Council, 2003, and references cited therein.
• Examples of known herbicides which can be combined with the mixtures according to the invention are the following active substances (note: the compounds are either with the "common name” according to the International Organization for Standardization (ISO) or with the chemical name, if appropriate together with a common code number and always include all forms of application such as acids, salts, esters and isomers such as stereoisomers and optical isomers.
• ISO International Organization for Standardization
• 2,4-D acetochlor, acifluorfen, acifluorfen-sodium , Aclonifen, Alachlor, Alloxydim, Alloxydim-sodium, Ametryn, Amicarbazone, Amidosulfuron, Aminopyralid, Amitrole, Anilofos, Asulam, Atrazine, Azafenidine, Azimsulfuron, Beflubutamide, Benazoline, Benazolin-ethyl, Benfuresate, Bensulfuron-methyl, Bentazone, Benzfendizone, Benzobicyclone , Benzofenap, Bifenox, Bilanafos, Bispyribac-sodium, Bromacil, Bromobutide, Bromofenoxime, Bromoxynil, Butachlor, Butaf enacil, butenachlor, butraline, butroxydim, butylates, cafen
• Metazachlor methabenzthiazuron, methyldymrone, metobromuron, metolachlor, metosulam, metoxuron, metribuzin, metsulfuron-methyl, molinate, monolinuron, naproanilide, napropamide, neburon, nicosulfuron, norflurazon, orbencarb, oryzalin, oxadiargyl, oxadiazone, oxasulfuron, oxaziclomefone, oxyfluorfen, paraquat, Pelargonium acid, Pendimethalin, Pendralin, Penoxsulam, Pentoxazone, Pethoxamide, Phenmedipham, Picloram, Picolinafen, Pinoxaden, Piperophos, Pretilachlor, Primisulfuron-methyl, Profluazole, Profoxydim, Prometryn, Propachlor, Propanil, Propaquiza
• formulations present in commercial form may optionally be diluted in the usual way, e.g. by means of water. Dust-like preparations, ground or scattered granules and sprayable solutions are usually no longer diluted with other inert substances before use.
• 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 ingredients (A) and (B) were then applied as aqueous suspensions or emulsions with a water application rate of 600 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-safener combinations have a good herbicidal pre-emergence activity against a broad one
• 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 trefoil stage.
• the formulated as wettable powders or as emulsion concentrates compounds of the invention were in different dosages with a
• the herbicidal-safener combinations according to the invention also have a good herbicidal activity against a wide range of economically important weeds and weeds, even after emergence.

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• 2005
  • 2005-03-12 BR BRPI0509289-2A patent/BRPI0509289A/pt not_active IP Right Cessation
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  • 2005-03-12 WO PCT/EP2005/002672 patent/WO2005092103A1/de not_active Ceased
  • 2005-03-12 EA EA200601704A patent/EA011892B1/ru not_active IP Right Cessation
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  • 2005-03-12 PL PL05716020T patent/PL1732391T3/pl unknown
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