EP0778732A1 - Herbicides selectifs a base d'aryluraciles - Google Patents

Herbicides selectifs a base d'aryluraciles

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Publication number
EP0778732A1
EP0778732A1 EP95931171A EP95931171A EP0778732A1 EP 0778732 A1 EP0778732 A1 EP 0778732A1 EP 95931171 A EP95931171 A EP 95931171A EP 95931171 A EP95931171 A EP 95931171A EP 0778732 A1 EP0778732 A1 EP 0778732A1
Authority
EP
European Patent Office
Prior art keywords
methyl
ethyl
alkyl
methoxy
cyano
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Withdrawn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
EP95931171A
Other languages
German (de)
English (en)
Inventor
Hans-Joachim Santel
Markus Dollinger
Roland Andree
Mark Wilhelm Drewes
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 AG
Original Assignee
Bayer 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 AG filed Critical Bayer AG
Publication of EP0778732A1 publication Critical patent/EP0778732A1/fr
Withdrawn legal-status Critical Current

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Classifications

    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines

Definitions

  • the invention relates to new herbicidal, synergistic active ingredient combinations which consist of known aryluracils (or arylthiouracils - or compounds which are isomeric to these aryluracils or arylthiouracils) on the one hand and other known herbicides which belong to other classes of substances on the other and are particularly successful for selective weed control in various crops, in particular in maize.
  • Aryluracils (or aryl-thio-uracile) as broadly active herbicides are the subject of a number of patent applications (cf. WO-A 91/00278, US-P 4979982, US-P 5169430, EP-A 408382, EP-A 563384, US-P 5084084, US-P 5127935, US-P 5154755, DE-P 4327743, DE-P 4343451, DE-P 4414326.
  • the known aryl uracils (or aryl (thio) uracils) have a number of Efficacy gaps, especially against monocotyledon weeds.
  • aryluracils or arylthiouracils - or compounds which are isomeric to these aryluracils or arylthiouracil compounds
  • known herbicidal active compounds for example from the classes of the Alkylanilines, carboxylic acids, carboxamides, diazin (on) e or triazin (on) e, ureas, nitriles, thiocarbamates and triazolinones show pronounced synergistic effects with regard to the action against weeds and are particularly advantageous as broadly effective combination preparations for the selective control of both monocotyledons and of dicotyledon weeds, in the pre-emergence and post-emergence processes, in monocotyledon crops, such as, for example, maize.
  • the invention relates to synergistic herbicidal compositions, characterized by an effective content of an active ingredient combination consisting of
  • Q oxygen or sulfur
  • Q oxygen or sulfur
  • R represents hydrogen or halogen
  • R 2 represents halogen or cyano
  • R represents the grouping below
  • a 1 represents a single bond, represents oxygen, sulfur, -SO-, -SO 2 -, -CO- or the grouping -NA 4 -, wherein A 4 represents hydrogen, hydroxy, alkyl, alkoxy, aryl, alkylsulfonyl or arylsulfonyl , or (A 1 ) represents optionally substituted alkanediyl, alkenediyl, azaalkenediyl, alkindiyl, cycloalkanediyl, cycloalkenediyl or arendiyl,
  • a 2 represents a single bond, represents oxygen, sulfur, -SO-, -SO 2 -, -CO- or the grouping -NA 4 -, wherein A 4 represents hydrogen, alkyl, aryl, alkylcarbonyl, alkylsulfonyl or arylsulfonyl, or (A 2 ) stands for optionally substituted alkanediyl, alkenediyl, aza ⁇ alkenediyl, alkindiyl, cycloalkanediyl, cycloalkenediyl or arendiyl, and
  • R 4 represents hydrogen, halogen or optionally substituted alkyl
  • R 5 represents hydrogen, halogen or optionally substituted alkyl
  • R 6 represents hydrogen, hydroxy, amino or optionally substituted alkyl, alkoxy, alkenyl or alkynyl
  • active ingredients of group 2 which contains the following classes of compounds (a) to (j):
  • R 7 for each optionally substituted alkyl, alkenyl, alkynyl or
  • R 8 represents in each case optionally substituted alkyl, alkenyl, alkynyl or phenyl, and
  • R 9 represents optionally substituted heteroaryl
  • R 10 represents hydrogen, hydroxyl, amino or represents optionally substituted alkyl, alkenyl, alkynyl, alkoxy, alkenyloxy, alkynyloxy, alkylamino, alkenylamino, alkynylamino, alkylideneamino, dialkylamino, cycloalkyl, cycloalkylalkyl, aryl or arylalkyl,
  • R 11 for optionally substituted alkyl, alkenyl, alkynyl,
  • Alkylamino alkenylamino, alkynylamino, dialkylamino, cycloalkyl
  • R 12 stands for optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, arylalkyl, arylalkenyl or arylalkynyl;
  • alkyl anilines e.g. N- (l-ethyl-propyl) -3,4-dimethyl-2,6-dinitro-aniline (pendimethalin) or N, N-dipropyl-2,6-dinitro-4-trifluoromethyl-aniline (trifluralin);
  • carboxylic acids such as e.g. 3,6-dichloropyridine-2-carboxylic acid (clopyralid), 2,4-dichlorophenoxyacetic acid (2,4-D), 3,6-dichloro-2-methoxy-benzoic acid (Dicamba), 4 -Amino-3,5-dichloro-6-fluoropyridin-2-yl-oxyacetic acid (fluroxypyr), 2-amino-4- (hydroxymethylphosphinyl) butanoic acid ammonium salt (glufosinate ammonium), N-phosphonomethyl -glycir.
  • carboxylic acids such as e.g. 3,6-dichloropyridine-2-carboxylic acid (clopyralid), 2,4-dichlorophenoxyacetic acid (2,4-D), 3,6-dichloro-2-methoxy-benzoic acid (Dicamba), 4 -Amino-3,5-dichloro-6-fluoropyridin-2
  • carboxamides such as BN- (2-methoxy-l-methyl-ethyl) -N- (2-ethyl-6-methyl-phenyl) -2-chloroacetamide (metolachlor), N-ethoxymethyl-N- (2-ethyl-6-methylphenyl) -2-chloroacetamide (acetochlor), N-methoxy- methyl-N- (2,6-dimethyl-phenyl) -2-chloroacetamide (alachlor), N- (2-methoxy-l-methyl-ethyl) -N- (2,4-dimethyl-3-thienyl) -2-chloroacetamide (dimethenamid), N- (1H-pyrazol-1-ylmethyl) -N- (2,6-dimethylphenyl) - 2-chloroacetamide (metazachlor) or Ni-propyl-N -phenyl-2-chloroacetamide (propyl-
  • diazin (on) e, or triazin (on) e e.g. 2-chloro-4-ethylamino-6-i-propylamino-l, 3,5-triazine (atrazine), 3-i-propyl-lH-2, l, 3-benzothiadiazine-4 (3H) -one- 2,2-dioxide (bentazone), 2-chloro-4-ethylamino-6- (l-cyano-l-methyl-ethylamino) -l, 3,5-triazine (cyanazine), 4-amino-6-t- butyl-4,5-dihydro-3-methylthio-l, 2,4-triazin-5-one (metribuzin), O- (6-
  • ureas e.g. N- (4,6-Dimethoxy-pyrimidin-2-yl) -N- (3-chloro-4-methoxycarbonyl-1-methyl-pyrazol-5-yl-sulfonyl) urea (Clopyra-sulfurone), N-methoxy -N-methyl-N- [4- (3,4-dihydro-2-methoxy-2,4,4-trimethyl-2H-1 -benzopyran7-yl-oxy) phenyl] urea (metobenzuron), N- (4,6-Dimethoxy-pyrimidin-2-yl) -N '- (3-dimethylamino-carbonyl-pyridin-2-yl-sulfonyl) urea (nicosulfuron), N- (4,6-bis-difluoromethoxy -pyrimidin-2-yl) -N '- (2-methoxycarbonyl-phen
  • nitriles such as 3,5-dibromo-4-hydroxy-benzonitrile (bromoxynil) or 3,5-diiodo-4-hydroxy-benzonitrile (ioxynil);
  • thiocarbamates such as N-di-i-butyl-S-ethyl-thiocarbamate (butylates) or N-dipropyl-S-ethyl-thiocarbamate (EPTC);
  • Active substances from various groups of substances such as, for example, N-2,6-difluorophenyl-5-methyl- [l, 2,4] triazolo- [l, 5-a] pyrimidine-2-sulfonamide (flumet- sulam), l, -dimethyl-4,4'-bipyridinium chloride (paraquat) or 2- (2-chloro-4-methylsulfonyl-benzoyl) -l, 3-cyclohexanedione (sulcotrione),
  • compositions according to the invention are of particular interest
  • Q 1 represents oxygen or sulfur
  • Q 2 represents oxygen or sulfur
  • R 1 represents hydrogen, fluorine, chlorine or bromine
  • R 2 represents fluorine, chlorine, bromine, iodine or cyano
  • R 3 represents the grouping below
  • a 1 represents a single bond, represents oxygen, sulfur, -SO-, -SO 2 -, -CO- or the grouping -NA 4 -, wherein A 4 represents hydrogen, hydroxy, C, -C 4 alkyl, C r C 4 alkoxy, phenyl, C r C 4 - alkylsulphonyl or phenylsulphonyl, or (A 1) represents optionally fluorine-, chlorine- or bromine-substituted C j -C 6 - alkanediyl, C 2 -C 6 alkene diyl, C 2 -C 6 azaalkenediyl, C 2 -C 6 .
  • a 2 represents a single bond, represents oxygen, sulfur, -SO-, -SO 2 -, -CO- or the grouping -NA 4 -, wherein A 4 represents hydrogen, hydroxy, C, -C 4 alkyl, C r C 4 alkoxy, phenyl, C r C 4 alkylsulfonyl or phenylsulfonyl, or (A 2 ) is in each case optionally substituted by fluorine, chlorine or bromine, C 6 -C 6 -alkanediyl, C 2 -C 6 -alkenediyl, C 2 -C 6 azaalkenediyl, C 2 -C 6 _alkindiyl, C 3 -C 6 cycloalkanediyl, C 3 - C 6 cycloal
  • R 4 represents hydrogen, fluorine, chlorine, bromine or alkyl having 1 to 4 carbon atoms which is optionally substituted by fluorine and / or chlorine,
  • R 5 represents hydrogen, fluorine, chlorine, bromine or alkyl having 1 to 4 carbon atoms which is optionally substituted by fluorine and / or chlorine, and
  • R 6 represents hydrogen, hydroxy, amino or alkyl, alkoxy, alkenyl or alkynyl, each optionally substituted by fluorine, chlorine or cyano, each having up to 4 carbon atoms, and
  • R 7 represents alkyl, alkenyl, alkynyl or alkoxy, each of which is optionally substituted by halogen, cyano or CJ-J alkoxy, each having up to 6 carbon atoms,
  • R 8 represents in each case optionally substituted by halogen, cyano or C j -C 4 alkoxy alkyl, alkenyl or alkynyl each of up to 6 carbon atoms or is optionally substituted by halogen, cyano,
  • R 9 is optionally substituted by halogen, cyano, C r C 4 alkyl, C, - C 4 haloalkyl, C j -C 4 alkoxy or C, -C 4 -haloalkoxy l substitution Clearlys heteroaryl from the series 3 -Thiazol-2-yl, l, 2,4-thiadiazol-5-yl, l, 3,4-thiadiazol-2-yl, benzoxazol-2-yl, benzthiazol-2-yl; (b) carbamoyltriazolinones of the formula (III) in which
  • R 10 for hydrogen, hydroxyl, amino, for each optionally substituted by halogen or cyano-substituted alkyl, alkenyl, alkynyl, alkoxy, alkenyloxy, alkynyloxy, alkylamino, alkenylamino, alkynylamino, alkylideneamino or dialkylamino, each with up to 6 carbon atoms, each optionally by halogen, cyano or C, -C 4 - substituted alkyl cycloalkyl, cycloalkylalkyl having in each case 3 to 6 carbon atoms in the cycloalkyl groups and optionally 1 to 4 carbon atoms in the alkyl group, or represents in each case optionally halogen-, cyano, C j -C 4 - alkyl or C 1 -C 4 alkoxy-substituted phenyl or phenyl-C 1 -C 4 alkyl,
  • R 11 for alkyl, alkenyl, alkynyl, alkoxy, alkenyloxy, alkynyloxy, alkylthio, alkenylthio, alkynylthio, alkylamino, alkenylamino, alkynylamino or dialkylamino, each optionally substituted by halogen, cyano, CC 4 alkoxy or C, -C 4 alkylthio each with up to 6 carbon atoms, for each cycloalkyl, cycloalkyloxy or cycloalkylalkyl optionally substituted by halogen, cyano or C 1 -C 4 -alkyl, each having 3 to 6 carbon atoms in the cycloalkyl groups and optionally 1 to 4 carbon atoms in the alkyl group , or for each if necessary by
  • R 12 for each optionally halogen, cyano, C j -C 4 alkoxy, C j - C 4 alkylthio, C r C 4 alkylsulfonyl, C r C 4 alkylsulfonyl, C, -C 4 alkylamino or Di- (C 1 -C 4 -alkyl) -amino-substituted alkyl, alkenyl, alkynyl each having up to 10 carbon atoms, for cycloalkyl or cycloalkylalkyl, each having 3 or optionally substituted by halogen, cyano or C ] -C 4 -alkyl up to 6 carbon atoms in the cycloalkyl part and optionally 1 to 4 carbon atoms in the alkyl part, for each optionally by halogen, Cyano, C r C 4 alkyl or C j -C 4 alkoxy substituted phenyl-C r C 6
  • alkyl anilines e.g. N- (l-ethyl-propyl) -3,4-dimethyl-2,6-dinitro-aniline (pendimethalin) or N, N-dipropyl-2,6-dinitro-4-trifluoromethyl-aniline (trifluralin);
  • carboxylic acids such as e.g. 3,6-dichloropyridine-2-carboxylic acid (clopyralid), 2,4-dichlorophenoxyacetic acid (2,4-D), 3,6-dichloro-2-methoxy-benzoic acid (Dicamba), 4 -Amino-3,5-dichloro-6-fluoropyridin-2-yl-oxy-acetic acid (fluroxypyr), 2-amino-4- (hydroxymethyl-phosphinyl l) -butanoic acid- ammonium salt (glufosinate-ammonium), N-
  • carboxylic acids such as e.g. 3,6-dichloropyridine-2-carboxylic acid (clopyralid), 2,4-dichlorophenoxyacetic acid (2,4-D), 3,6-dichloro-2-methoxy-benzoic acid (Dicamba), 4 -Amino-3,5-dichloro-6-fluoropyridin-2-y
  • Phosphonomethyl-glycine glyphosate
  • 2- (4,5-dihydro-4-methyl-4-i-propyl-5-oxo-lH-imidazol-2-yl) -5-ethyl-pyridine-3-carboxylic acid Ima - zethapyr
  • 2- (4,5-dihydro-4-methyl-4-i-propyl-5-oxo-1H-imidazol-2-yl) -quinoline-3-carboxylic acid imazaquine
  • carboxamides such as N- (2-methoxy-l-methyl-ethyl) -N- (2-ethyl-
  • 6-methyl-phenyl) -2-chloroacetamide metal-ethoxymethyl-N- (2-ethyl-6-methyl-phenyl) -2-chloroacetamide (acetochlor), N-methoxy-methyl-N - (2,6-dimethyl-phenyl) -2-chloroacetamide (alachlor), N- (2-methoxy-l-methyl-ethyl) -N- (2,4-dimethyl-3-thienyl) -2- chloroacetamide (dimethenamid), N- (lH-pyrazol-l-yl-methyl) -N- (2,6-dimethyl-phenyl) -
  • 2-chloroacetamide metalazachlor
  • N-i-propyl-N-phenyl-2-chloroacetamide propachlor
  • diazin (on) e, or triazin (on) e such as. 2-chloro-4-ethylamino-6-i-propyl-mino-l, 3,5-triazine (atrazine), 3-i-propyl-lH-2J, 3-benzothiadiazine-4 (3H) -one -2,2-dioxide (bentazone), 2-chloro-4-ethylamino-6- (l-cyano-1-methyl-ethylamino) -l, 3,5-triazine (cyanazine), 4-amino-6-t -butyl-4,5-di-hydro-3-methylthio-l, 2,4-triazin-5-one (metribuzin), O- (6-chloro-3-phenyl-4-pyridazinyl) -S- octyl thiocarbonate (pyridate); 2-chloro-4,6-bis-ethylamino-l, 3,5-triazin
  • nitriles such as 3,5-dibromo-4-hydroxy-benzonitrile (bromoxynil) or 3,5-diiodo-4-hydroxy-benzonitrile (ioxynil);
  • thiocarbamates such as e.g. N-di-i-butyl-S-ethyl-thiocarbamate (butylate) or N-dipropyl-S-ethyl-thiocarbamate (EPTC);
  • active substances from various substance groups e.g. N-2,6-difluorophenyl-5-methyl- [l, 2,4] triazolo- [l, 5-a] pyrimidine-2-sulfonamide (flumet-sulam), l. -DimethyM ⁇ '- bipyridinium chloride ⁇ araqua ⁇ or 2- (2-
  • 1 to 1 part by weight of active ingredient in group 1 is preferably 0.01 to 100 parts by weight of active ingredient in group 2.
  • Herbicidal compositions according to the invention are of very particular interest
  • Q 1 represents oxygen or sulfur
  • Q 2 represents oxygen or sulfur
  • R 1 represents hydrogen, fluorine, chlorine or bromine
  • R 2 represents fluorine, chlorine, bromine, iodine or cyano
  • R 3 represents the grouping below
  • a 1 represents a single bond, represents oxygen, sulfur, -SO-, -SO 2 -, -CO- or the grouping -NA 4 -, wherein A 4 represents hydrogen, hydroxy, methyl, ethyl, n- or i-propyl , Methoxy, ethoxy, n- or i-propoxy, methylsulfonyl or ethylsulfonyl, or (A 1 ⁇ is methylene, ethane-1, 1-diyl, ethane-1, 2-diyl, propane-1, 1-diyl, propane - 1,2-diyl, propane-1,3-diyl, ethene-1,2-diyl, propene-1,2-diyl, propene-1,3-diyl, ethyne-1,2-diyl, propyne-1 , 2-diyl or propin-1,3-diyl,
  • a 2 represents a single bond, represents oxygen, sulfur, -SO-, -SO 2 -, -CO- or the grouping -NA 4 -, wherein A 4 represents hydrogen, hydroxy, methyl, ethyl, n- or i-propyl , Methoxy, ethoxy, n- or i-propoxy, methylsulfonyl, ethylsulfonyl, n- or i-propylsulfonyl or phenylsulfonyl, or (A 2) is methylene, ethane-1,1-diyl, ethane-1,2-diyl, Propane-1,1-diyl, propane-1,2-diyl, propane-l, 3-diyl, ethene-1,2-diyl, propene-1,2-diyl, propene-1,3-diyl, ethyne 1,2-diyl, prop
  • Pentyloxy methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, methyl sulfinyl, ethylsulfinyl, n- or i-propylsulfinyl, methylsulfonyl, ethylsulfonyl, n- or i-propylsulfonyl, methylamino , Ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino, dimethylamino, diethylamino, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, dimethoxyphosphoryl, diethoxyphosphoryl, dipropoxyphosphoryl or diisopropoxyphosphoryl, for each in each case
  • R 4 represents hydrogen, fluorine, chlorine or methyl or ethyl which is optionally substituted by fluorine and / or chlorine
  • R 5 stands for hydrogen, fluorine, chlorine or for methyl or ethyl optionally substituted by fluorine and / or chlorine
  • R 6 stands for hydrogen, hydroxyl, amino or for methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- or i-propoxy, propenyl or propynyl which is optionally substituted by fluorine, chlorine or cyano, and
  • R 7 for each optionally by fluorine, chlorine, cyano, methoxy or
  • R 8 represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-, each of which is optionally substituted by fluorine, chlorine, cyano, methoxy or ethoxy
  • R 9 for each optionally by fluorine, chlorine, bromine, cyano, methyl
  • R 11 for each methyl, ethyl, n- or i-propyl, n-, i-, substituted by fluorine, chlorine, cyano, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio , s- or t-butyl, propenyl, butenyl, propynyl, butynyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, propenyloxy, butenyloxy, propynyloxy, butynyloxy, Methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, propenylthio, butenylthio, propinyl
  • alkyl anilines e.g. N- (l-ethyl-propyl) -3,4-dimethyl-2,6-dinitro-aniline (pendimethalin) or N, N-dipropyl-2,6-dinitro-4-trifluoromethyl-aniline (trifluralin);
  • carboxylic acids such as e.g. 3,6-dichloropyridine-2-carboxylic acid (clopyralid), 2,4-dichlorophenoxyacetic acid (2,4-D), 3,6-dichloro-2-methoxybenzoic acid (dicamba), 4-amino -3,5-dichloro-6-fluoropyridine-2-yl-oxy-acetic acid (fluroxypyr), 2-amino-4- (hydroxymethyl-phosphinyl) butanoic acid ammonium salt (glufosinate ammonium), N-
  • Phosphonomethyl-glycine glyphosate
  • 2- (4,5-dihydro-4-methyl-4-i-propyl-5-oxo-1 H-imidazol-2-yl) -5-ethyl-pyridine-3-carboxylic acid Imaz-ethapyr
  • 2- (4,5-dihydro-4-methyl-4-i-propyl-5-oxo-1H-imidazol-2-yl) -quinoline-3-carboxylic acid imazaquine
  • carboxamides such as N- (2-methoxy-l-methyl-ethyl) -N- (2-ethyl-
  • 6-methyl-phenyl) -2-chloroacetamide metal-chloroacetamide
  • metalachlor N-ethoxymethyl-N- (2-ethyl-6-methyl-phenyl) -2-chloroacetamide
  • acetochlor N-methoxy- methyl-N- (2,6-dimethyl-phenyl) -2-chloroacetamide
  • alachlor N- (2-methoxy-1-methyl-ethyl) -N- (2,4-dimethyl-3-thienyl) -2-chloroacetamide (dimethenamid), N- (1H-pyrazol-1-ylmethyl) -N- (2,6-dimethylphenyl) - 2-chloroacetamide (metazachlor) or Ni-propyl-N -phenyl-2-chloroacetamide (propachlor);
  • diazin (on) e, or triazin (on) e e.g. 2-chloro-4-ethylamino-6-i-propylamino-l, 3,5-triazine (atrazine), 3-i-propyl-lH-2, l, 3-benzothia-diazin-4 (3H) -one- 2,2-dioxide (bentazone), 2-chloro-4-ethylamino-6- (l-cyano-l-methyl-ethylamino) -l, 3,5-triazine (cyanazine), 4-amino-6-t- butyl-4,5-c hydro-3-methylthio-l, 2,4-triazin-5-one (metribuzin), O- (6-
  • ureas such as N- (4,6-dimethoxy-pyrimidin-2-yl) -N- (3-chloro-4-methoxycarbonyl-l-methyl-pyrazol-5-yl-sulfonyl) -ha ⁇ stoff (Clopyra - sulognion), N-methoxy-N-methyl-N- [4- (3,4-dihydro-2-methoxy-2,4,4-trimethy 1-2H-1 -benzopyran7-yl-oxy) phenyl] urea (metobenz uron), N- (4,6-dimethoxy-pyrimidin-2-yl) -N '- (3-dimethylamino-carbonyl-pyridin-2-yl-sulfonyl) urea (nicosulfuron), N- (4,6-bis-difluoromethoxy-pyrimidin-2-yl) -N , - (2-methoxy
  • nitriles such as 3,5-dibromo-4-hydroxy-benzonitrile (bromoxynil) or 3,5-diiodo-4-hydroxy-benzonitrile (ioxynil);
  • thiocarbamates such as N-di-i-butyl-S-ethyl-thiocarbamate (butylates) or N-dipropyl-S-ethyl-thiocarbamate (EPTC);
  • Active substances from various groups of substances such as, for example, N-2,6-difluorophenyl-5-methyl- [1, 2,4] -triazolo- [1, 5-a] -pyrimidine-2-sulfonamide (flumet- sulam), l, -dimethyl-4,4'-bipyridinium chloride (paraquat) or 2- (2-chloro-4-methylsulfonyl-benzoyl) - 1, 3 -cyclohexanedione (sulcotrione),
  • active compound of the general formula (II) 0.1 to 10 parts by weight of active compound of the general formula (II) are preferably used per 1 part by weight of active compound of the general formula (I).
  • Examples of the compounds of the formula (I) to be used as mixing partners according to the invention are: 1- (4-chloro-3-methylsulfonylamino-phenyl) -3,6-dihydro-2,6-dioxo-3- methyl-4-trifluoromethyl-1 (2H) -pyrimidine, 1 - (4-chloro-3-methylsulfonylamino-phenyl) -3,6-dihydro-2,6-dioxo-3-amino-4-trifluoromethyl -l (2H) -pyrimidine, l- (4-cyano-3-methylsulfonylamino-phenyl) -3,6-dihydro-2,6-dioxo-3-methyl-4-trifluoromethyl-l (2H) -pyrimidine , l- (4-Chloro-3-ethylsulfonylamino-phenyl) -3,6-dihydro-2,6-di
  • Examples of the compounds of the formula (II) to be used as mixture partners according to the invention are: N-methyl-N-phenyl- ⁇ - (5-trifluoromethyl-l, 3,4-thiadiazol-2-yl-oxy ) -acetamide, N-ethyl-N-phenyl- ⁇ - (5-trifluoromethyl-l, 3,4-thiadiazol-2-yl-oxy) -acetamide, Nn-propyl-N-phenyl- ⁇ - (5th -trifluoromethyl-1, 3, 4-thiadiazol-2-yl-oxy) -acetamide, Ni-propyl-N-phenyl- ⁇ - (5-trifluoromethyl-1, 3, 4-thiadiazol-2-yl-oxy) - acetamide, N-methyl-N- (4-fluoro-phenyl) - ⁇ - (5-trifluoromethyl-l, 3,4-thiadiazol-2-yl-oxy) -acetamide, N-ethyl-N- (4
  • the compounds of the formula (II) are known and / or can be prepared by known processes (cf. EP-A 5501, EP-A 18497, EP-A 29171, EP-A 94514, EP-A 100044, EP-A 100045 , EP-A 161602, EP-A 195237, EP-A 348734, EP-A 348737).
  • the compounds of the formula (III) are likewise known and / or can be prepared by known processes (cf. EP-A 294666, EP-A 370293, EP-A 391187, EP-A 398096, EP-A 399294, EP -A 415196, EP-A 477646).
  • the active substance combinations defined above from the aryluracils (or arylthiouracils) of the formula (I) and the active substances mentioned above under Group 2 have a particularly high herbicidal activity and in different crops, in particular in maize , but can also be used in soy, sunflowers, wheat, barley and sugar cane for selective weed control.
  • the herbicidal activity of the active compound combinations according to the invention is considerably higher than the sum of the effects of the individual active compounds.
  • the new drug combinations are available in a number of cultures, e.g. in maize, soybeans and sugar cane, well tolerated, whereby the new active ingredient combinations also cover weeds that are otherwise difficult to control.
  • the new active ingredient combinations thus represent a valuable addition to the selective herbicides, especially the herbicides that can be used in maize.
  • weeds which can be controlled well by the active compound combinations according to the invention are:
  • the active compound combinations according to the invention have an excellent action against weeds and grasses, while being well tolerated by maize crops. Their use as selective herbicides in maize should therefore be particularly emphasized.
  • the synergistic effect of the active compound combinations according to the invention is particularly pronounced at certain concentration ratios.
  • the weight ratios of the active ingredients in the active ingredient combinations can be varied within relatively large ranges.
  • 1 part by weight of group 1 active ingredient accounts for 0.001 to 1000 parts by weight, preferably 0.01 to 100 parts by weight, particularly preferably 0.1 to 10 parts by weight of group 2 active ingredient.
  • the active ingredients can be converted into the customary formulations, such as solutions, emulsions, wettable powders, suspensions, powders, dusts, pastes, soluble powders, granules, suspension emulsion concentrates, active ingredient-impregnated natural and synthetic substances and very fine encapsulations in polymers Fabrics.
  • formulations are prepared in a known manner, e.g. B. by mixing the active ingredients with extenders, that is liquid solvents and / or solid carriers, if appropriate using surface-active agents, ie emulsifiers and / or dispersants and / or foam-generating agents.
  • organic solvents can, for example, also be used as auxiliary solvents.
  • auxiliary solvents essentially suitable as liquid solvents: aromatics, such as xylene, toluene, or alkylnaphthalenes, chlorinated aromatics and chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chloroethylene or methylene chloride, aliphatic hydrocarbons, - 24 -
  • cyclohexane or paraffins e.g. Petroleum fractions, mineral and vegetable oils, alcohols such as butanol or glycol as well as their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents such as dimethylformamide and dimethyl sulfoxide, and water.
  • Possible solid carriers are e.g. Ammonium salts and natural rock powders such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and synthetic rock powders such as highly disperse silica, aluminum oxide and silicates are suitable as solid carriers for granules: e.g. broken and fractionated natural rocks such as calcite, marble, pumice, sepiolite, dolomite and synthetic granules from inorganic and organic flours and granules from organic material such as sawdust, coconut shells, corn cobs and tobacco stems; as emulsifying and / or foaming agents are possible: e.g.
  • nonionic and anionic emulsifiers such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, e.g. Alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates and protein hydrolyzates;
  • Possible dispersants are: e.g. Lignin sulfite liquor and methyl cellulose.
  • Adhesives such as carboxymethyl cellulose, 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 can be used in the formulations.
  • Other additives can 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 can be used.
  • the formulations generally contain between 0J and 95 percent by weight of active compound, preferably between 0.5 and 90%.
  • the active compound combinations according to the invention are generally used in the form of finished formulations.
  • the one in the drug combinations Active ingredients contained can also be mixed in individual formulations when used, ie applied in the form of tank mixtures.
  • the new active ingredient combinations can furthermore also be used in a mixture with other known maize herbicides for weed control, ready-to-use formulations or tank mixes being possible.
  • a mixture with other known active compounds such as fungicides, insecticides, acaricides, nematicides, bird repellants, growth agents, plant nutrients and agents which improve soil structure, is also possible.
  • mineral or vegetable oils e.g. the commercially available "Oleo Dupont 11E”
  • ammonium salts such as e.g. Include ammonium sulfate or ammonium rhodanide.
  • the active compound combinations according to the invention can be used as such, in the form of their formulations or in the use forms prepared therefrom by further dilution, such as ready-to-use solutions, suspensions, emulsions, powders, pastes and granules. They are used in the usual way, e.g. by watering, spraying, spraying or sprinkling.
  • the active compound combinations according to the invention can be applied both before and after emergence of the plants. They can also be worked into the soil before sowing.
  • the active compound combinations according to the invention can (a) in conventional cultivation of maize ("conventional tillage") both in advance! on-procedure as well in the post-emergence process or (b) in the gentle cultivation of maize ("preplant bumdown").
  • the application rates of the active compound combinations according to the invention can be varied within a substantial range. They essentially depend on the type of effect desired. In general, the application rates are between 10 g and 10 kg of active ingredient combination per hectare of soil, preferably between 50 g and 5 kg per ha, in particular between 100 g and 2 kg per ha.
  • Herbicides always have a synergistic effect if the herbicidal activity of the active ingredient combination is greater than that of the individual active ingredients applied.
  • the expected effect for a given combination of two herbicides can be calculated as follows (cf. Colby, S. R; "Calculating synergistic and antagonistic responses of herbicide combinations", Weeds 15, pages 20-22, 1967):
  • Y % damage by herbicide B (active ingredient of group 2) at q kg / ha application rate
  • the effect of the combination is super-additive, i.e. it shows a synergistic effect.
  • the application tests for the active compound combinations according to the invention show that the herbicidal activity of the active compound combinations according to the invention is greater than the calculated, i.e. that the new drug combinations work synergistically.

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

Abstract

L'invention concerne de nouvelles associations synergiques herbicides de substances actives, comprenant, d'une part, des aryluraciles connus (tels que aryl-thiouraciles ou des composés isomères de ces aryluraciles ou de ces aryl-thiouraciles) et, d'autre part, d'autres herbicides connus appartenant à d'autres classes de substances, lesdites associations pouvant être utilisées de façon particulièrement efficace pour lutter sélectivement contre les mauvaises herbes dans diverses cultures de plantes utiles, notamment de maïs.
EP95931171A 1994-09-02 1995-08-21 Herbicides selectifs a base d'aryluraciles Withdrawn EP0778732A1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE4431219A DE4431219A1 (de) 1994-09-02 1994-09-02 Selektive Herbizide auf Basis von Aryluracilen
DE4431219 1994-09-02
PCT/EP1995/003313 WO1996007323A1 (fr) 1994-09-02 1995-08-21 Herbicides selectifs a base d'aryluraciles

Publications (1)

Publication Number Publication Date
EP0778732A1 true EP0778732A1 (fr) 1997-06-18

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Country Link
US (1) US5990044A (fr)
EP (1) EP0778732A1 (fr)
JP (1) JPH10505072A (fr)
CN (2) CN1079639C (fr)
AU (1) AU3471595A (fr)
BR (1) BR9508690A (fr)
CA (1) CA2198742A1 (fr)
DE (1) DE4431219A1 (fr)
HK (2) HK1001276A1 (fr)
MX (1) MX9701553A (fr)
WO (1) WO1996007323A1 (fr)

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CN1156394A (zh) 1997-08-06
HK1049094A1 (zh) 2003-05-02
HK1001276A1 (en) 1998-06-12
CN1370406A (zh) 2002-09-25
DE4431219A1 (de) 1996-03-07
BR9508690A (pt) 1998-05-26
WO1996007323A1 (fr) 1996-03-14
JPH10505072A (ja) 1998-05-19
CN1079639C (zh) 2002-02-27
CA2198742A1 (fr) 1996-03-14
US5990044A (en) 1999-11-23
AU3471595A (en) 1996-03-27
MX9701553A (es) 1997-05-31

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