WO1994022310A1 - Herbicides contenant une ou plusieurs substances actives herbicides du groupe des derives d'acide salicylique et un ou plusieurs composes antidotes - Google Patents

Herbicides contenant une ou plusieurs substances actives herbicides du groupe des derives d'acide salicylique et un ou plusieurs composes antidotes Download PDF

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Publication number
WO1994022310A1
WO1994022310A1 PCT/EP1994/000862 EP9400862W WO9422310A1 WO 1994022310 A1 WO1994022310 A1 WO 1994022310A1 EP 9400862 W EP9400862 W EP 9400862W WO 9422310 A1 WO9422310 A1 WO 9422310A1
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Prior art keywords
alkyl
carry
alkoxy
phenyl
halogen
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PCT/EP1994/000862
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German (de)
English (en)
Inventor
Matthias Bratz
Uwe Josef Vogelbacher
Joachim Rheinheimer
Ernst Baumann
Andreas Landes
Helmut Walter
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Basf Aktiengesellschaft
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Priority to AU64280/94A priority Critical patent/AU6428094A/en
Publication of WO1994022310A1 publication Critical patent/WO1994022310A1/fr

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    • 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 present invention relates to herbicidal compositions comprising a) one or more herbicidal active compounds from the group of the salicylic acid derivatives of the formulas Ia and / or Ib
  • R 1 is hydrogen, succinyliminooxy, alkyl, alkylcarbonyl, alkoxycarbonyl;
  • 5-membered heteroaryl containing one to three nitrogen atoms which can carry one or two of the following substituents: halogen, alkyl, haloalkyl, alkoxy, haloalkoxy, alkylthio and, if desired, additionally as many halogen atoms as there are further substitutable ring members;
  • R 2 , R 3 halogen, alkyl, haloalkyl, alkoxy, haloalkoxy, alkylthio, alkylamino or dialkylamino;
  • R 4 is hydrogen, cyano, C (O) NH 2 , alkyl or alkylcarbonyl;
  • R 5 is hydrogen
  • R 6 is hydrogen, an alkali metal cation, the equivalent of an alkaline earth metal cation or an organic ammonium ion;
  • Cycloalkyl which can carry one to three alkyl radicals; Alkyl which can carry one to five halogen atoms and / or one of the following radicals:
  • Cyano, alkoxy, alkylthio, alkylcarbonyl, alkoxycarbonyl, cycloalkyl, -ON CR 10 R 11 , phenyl, phenoxy or phenylcarbonyl, where the phenyl rings can in turn carry one to three of the following substituents: halogen, alkyl, haloalkyl, alkoxy, haloalkoxy, alkylthio and the phenyl rings can additionally carry so many halogen atoms that the total number of substituents is 4 or 5;
  • Alkyl which can carry one to five halogen atoms and which carries a 5-membered heteroaryl radical which contains one to three nitrogen atoms and in turn one or two of the following
  • Halogen atoms such as further substitutable ring members are present;
  • Alkyl which has one of the following radicals in the 2-position: alkoxyimino, alkenyloxyimino, haloalkenyloxyimino or benzyloxyimino; Alkenyl or alkynyl, these radicals in turn being able to carry one to five halogen atoms;
  • Phenyl which can carry one to three of the following substituents: halogen, alkyl, alkoxy and, if desired, so many halogen atoms that the total number of substituents is 4 or 5; nitrogen-bonded 5-membered heteroaryl containing one to four nitrogen atoms, or nitrogen-bonded benzo-fused 5-membered heteroaryl containing one to three nitrogen atoms, these rings being able to be substituted by halogen, alkyl and / or haloalkyl;
  • R 7 , R 8 are hydrogen;
  • Alkyl, alkenyl or alkynyl which can carry one to five halogen atoms and / or one or two of the following substituents: halogen, cyano, alkoxy, alkenyloxy, alkynyloxy, alkylthio, alkenylthio, alkynylthio, haloalkoxy, alkylcarbonyl, alkenylcarbonyl, alkynylcarbonyl, alkoxycarbonyl, alkenyloxycarbonyl , Alkynyloxycarbonyl, dialkylamino, cycloalkyl and
  • Halogen atoms that the total number of substituents is 3, 4 or 5;
  • Cycloalkyl which can carry one to three alkyl radicals; if necessary subst. Phenyl;
  • R 7 and R 8 together alkylenediyl, which is an oxygen
  • R 9 May contain sulfur or nitrogen atom, and which may carry one to three alkyl radicals; R 9 alkyl, which can carry one to four of the following radicals: nitro, cyano, halogen;
  • Phenyl which can carry one to four of the following radicals: nitro, cyano, halogen, alkyl;
  • R 10 , R 11 alkyl which can carry a phenyl radical, an alkoxy and / or an alkylthio group; Alkoxy or phenyl; or
  • R 10 and R 11 together alkylenediyl or alkenylenediyl, which can carry a phenyl radical or one to five alkyl groups and which can be bridged by an alkylene chain;
  • R 12 is alkyl, alkenyl and alkynyl
  • R 13 is hydrogen
  • Alkyl which can carry the following radicals: hydroxy, amino, hydrogen sulfide, alkylthio, carboxy, carbamoyl, guanidinyl, phenyl, hydroxyphenyl, imidazolyl, indolyl; or
  • R 13 and R 7 together alkylene diyl; m 0 or 1; n 0, 1 or 2;
  • Nitrogen atoms and a sulfur or oxygen atom which can carry one to three halogen atoms and / or one to three of the following radicals: nitro, cyano, alkyl, alkylthio, haloalkyl and phenyl, which in turn can carry one to three halogen atoms and / or methyl groups; or - 6-membered heteroaryl containing one to three nitrogen atoms, which can carry one to three halogen atoms and / or one to three of the following radicals: nitro, cyano, alkyl, alkylthio, haloalkyl; if necessary subst. Phenyl, phenoxy, phenylthio or phenylsulfonyl; 5-membered heteroaryl containing one to four
  • Nitrogen atoms or one to three nitrogen atoms and one oxygen or sulfur atom which can carry one to three halogen atoms and / or one to three of the following radicals: nitro, cyano, alkyl, alkoxy, alkylthio, haloalkyl,
  • Phenyl which in turn is one to three
  • Sulfur atom which can carry one to three of the following radicals: cyano, halogen, alkyl; Thienyl or furyl, which is one to three
  • 6-membered heteroaryl containing one to four nitrogen atoms which can carry one to three halogen atoms and / or one to three of the following radicals: nitro, cyano, alkyl, alkoxy, alkylthio, haloalkyl, phenyl, which in turn has one to three halogen atoms and / or can carry methyl groups;
  • R 1 ' for one of the groups mentioned under R 1
  • R ' is hydrogen or
  • R '' represents hydrogen, alkyl or one of the groups mentioned under R; and one or more compounds of the formulas Ila and / or Ilb
  • X a is hydrogen, nitro, halogen, C 1 -C 4 alkyl
  • R b is hydrogen, C 1 -C 6 alkyl, C 1 -C 6 alkoxy or optionally
  • R b and R c together with the N atom to which they are bonded are saturated or unsaturated 3 to
  • 7-membered heterocyclyl which has one or two further heteroatoms selected from the group May contain nitrogen, oxygen and sulfur, and this ring can carry one to three of the following radicals: C 1 -C 4 alkyl, C 1 -C 4 alkoxy, optionally subst. Phenyl;
  • R c is hydrogen
  • C 1 -C 4 alkyl Di- (C 1 -C 4 alkyl) amino, C 1 -C 8 alkylcarbonyl, C 2 -C 8 alkenylcarbonyl, C 2 -C 8 alkynylcarbonyl, C 1 -C 8 alkoxycarbonyl, C 1 -C 8 -alkylthiocarbonyl, C 2 -C 8 -alkenyloxycarbonyl, C 2 -C 8 -alkynyloxycarbonyl, 1- (hydroxyimino) -C 1 -C 6 -alkyl,
  • Phenyl- (C 1 -C 6 alkyl) carbonylamino where the phenyl radicals in turn can carry the following radicals: nitro, halogen, C 1 -C 4 alkyl, C 1 -C 4 -H-alogenalkyl, C 1 -C 4 -Alkoxy and
  • R d is hydrogen, C 1 -C 4 -alkyl or phenyl, which can carry one or more of the following groups: nitro, halogen, C 1 -C 4 -alkyl, C 1 -C 4 -halogen-
  • R e C 1 -C 4 alkyl; or two R e in adjacent positions together C 1 -C 6 alkylene;
  • R f is hydrogen or C 1 -C 4 alkyl; a 1 to 5; b 1 to 5;
  • R g is hydrogen, C 1 -C 8 alkyl, C 1 -C 8 haloalkyl,
  • R h is hydrogen, C 1 -C 8 alkyl, C 3 -C 12 cycloalkyl,
  • Tri- (C 1 -C 4 alkoxy) silyl Tri- (C 1 -C 4 alkoxy) silyl.
  • the invention relates to methods for the selective control of undesirable plant growth on cultivated areas of crop plants with these herbicidal compositions.
  • Herbicidal salicylic acid derivatives of the formula Ia or Ib are known from the literature (EP-A 223 406, EP-A 249 708, EP-A 287 072, EP-A 287 079, EP-A 315 889, EP-A 360 163, EP-A 402 751, EP-A 435 170, EP-A 414 058, EP-A 426 476, EP-A 451 653, EP-A 467 139, EP-A 479 055, EP-A 490 224, EP- A 493 321, DE-A 41 26 936, DE-A 41 26 937).
  • herbicidal salicylic acid derivatives of the formulas Ia and Ib have a comparison with those described in EP-A 521 407
  • herbicidal compositions which contain the salicylic acid derivatives of the formulas Ia and Ib and which ensure good control of undesirable plants without appreciably damaging the useful or crop plants or impairing their crop yield.
  • Alkyl straight-chain or branched alkyl groups with 1 to 20 carbon atoms
  • Alkylamino an amino group bearing a straight-chain or branched alkyl group having 1 to 20 carbon atoms
  • Dialkylamino an amino group which carries two independent, straight-chain or branched alkyl groups each having 1 to 20 carbon atoms;
  • Alkylcarbonyl straight-chain or branched alkyl groups with 1 to 20 carbon atoms, which are bonded to the skeleton via a carbonyl group (-CO-);
  • Alkylcarbonyloxy straight-chain or branched alkyl groups with 1 to 6 carbon atoms, which have a carbonyloxy group
  • Alkylcarbonylamino straight-chain or branched alkyl groups with 1 to 8 carbon atoms, which are bonded to the skeleton via a carbonylamino group (-CO-NH-);
  • Alkylaminocarbonylamino straight-chain or branched alkyl groups with 1 to 8 carbon atoms, which are bonded to the skeleton via an aminocarbonylamino group (-NH-CO-NH-);
  • Dialkylaminocarbonyl an amino group which carries two independent, straight-chain or branched alkyl groups each having 1 to 6 carbon atoms and which is bonded to the skeleton via a carbonyl group;
  • Alkylsulfonyl straight-chain or branched alkyl groups with 1 to 20 carbon atoms, which are bonded to the skeleton via a sulfonyl group (-SO 2 -);
  • Hydroxyalkyl straight-chain or branched alkyl groups with 1 to 6 carbon atoms, which carry a hydroxy group in any position;
  • Alkylaminocarbonyl straight-chain or branched alkyl groups with 1 to 8 carbon atoms, which are bonded to the skeleton via an aminocarbonyl group (-NH-CO-);
  • Phenylalkylcarbonylamino alkylcarbonylamino groups with 1 to 6 carbon atoms in the alkyl part as mentioned above, which carry a phenyl group in any position of the alkyl part;
  • Trialkylsilyl a silyl group which carries three independent, straight-chain or branched alkyl groups each having 1 to 4 carbon atoms: trimethylsilyl, triethylsilyl, triisopropylsilyl and t-butyldimethylsilyl;
  • Phenyldialkylsilyl a silyl group which carries a phenyl ring and two independent, straight-chain or branched alkyl groups each having 1 to 4 carbon atoms, e.g. Phenyldimethylsilyl;
  • Trialkoxysilyl a silyl group which carries three independent, straight-chain or branched alkoxy groups each having 1 to 4 carbon atoms, for example triisopropoxysilyl;
  • Haloalkyl straight-chain or branched alkyl groups with 1 to 4 carbon atoms, these groups being able to partially or completely replace the hydrogen atoms by halogen atoms as mentioned above, for example C 1 -C 2 -haloalkyl such as chloromethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl , Chlorofluoromethyl, dichlorofluoromethyl,
  • Chlorodifluoromethyl 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro-2- fluoroethyl, 2,2,2-trichloroethyl and pentafluoroethyl;
  • Alkoxy straight-chain or branched alkoxy groups with 1 to 20 carbon atoms
  • Alkoxyalkyl straight-chain or branched alkyl groups with 1 to 4 carbon atoms, which in any position carry a straight-chain or branched alkoxy group with 1 to 4 carbon atoms;
  • Alkoxycarbonyl straight-chain or branched alkoxy groups with 1 to 20 carbon atoms, which are bonded to the skeleton via a carbonyl group (-CO-);
  • Phenoxyalkoxy straight-chain or branched alkoxy groups with 1 to 6 carbon atoms in the alkyl part, which carry a phenoxy group in any position of the alkyl radical;
  • Phenylalkoxycarbonyl straight-chain or branched alkoxycarbonyl groups with 1 to 6 carbon atoms in the alkyl part which carry a phenyl group in any position of the alkyl radical;
  • Phenoxyalkoxycarbonyl straight-chain or branched alkoxycarbonyl groups with 1 to 6 carbon atoms in the alkyl part which carry a phenyl group in any position of the alkyl radical;
  • Haloalkoxy straight-chain or branched alkoxy groups having 1 to 4 carbon atoms, these groups being able to be partially or completely replaced by halogen atoms as mentioned above in groups;
  • Alkylthio straight-chain or branched alkylthio groups with 1 to 20 carbon atoms;
  • Alkylthiocarbonyl straight-chain or branched alkylithio groups with 1 to 8 carbon atoms as mentioned above, which are bonded to the structure via a carbonyl group (-CO-);
  • Alkenyl straight-chain or branched alkenyl groups with 2 to 20 carbon atoms and a double bond in any position;
  • Alkenyloxy straight-chain or branched alkenyl groups with 2 to 20 carbon atoms and a double bond in any position;
  • Alkenylthio straight-chain or branched alkenylthio groups with 2 to 20 carbon atoms
  • Alkenylcarbonyl straight-chain or branched alkenyl groups with 2 to 20 carbon atoms, which are bonded to the skeleton via a carbonyl group (-CO-);
  • Alkenylcarbonyloxy straight-chain or branched alkenyl groups with 2 to 20 carbon atoms, which are bonded to the skeleton via a carbonyloxy group (-CO-O-);
  • Alkenylcarbonylamino straight-chain or branched alkenyl groups with 2 to 20 carbon atoms, which are bonded to the skeleton via a carbonylamino group (-CO-NH-);
  • Alkenylaminocarbonyl straight-chain or branched alkenyl groups with 2 to 20 carbon atoms, which are bonded to the skeleton via an aminocarbonyl group (-NH-CO-);
  • Alkenyloxycarbonyl straight-chain or branched alkenyloxy groups with 2 to 20 carbon atoms, which are bonded to the skeleton via a carbonyl group (-CO-);
  • Alkynyl straight-chain or branched alkynyl groups with 2 to 20 carbon atoms and a triple bond in any position
  • Alkynylcarbonyl straight-chain or branched alkynyl groups with 2 to 20 carbon atoms, which are bonded to the skeleton via a carbonyl group (-CO-);
  • Alkynylcarbonyloxy straight-chain or branched alkynyl groups with 2 to 20 carbon atoms, which are bonded to the skeleton via a carbonyloxy group (-CO-O-);
  • Alkynylcarbonylamino straight-chain or branched alkynyl groups with 2 to 20 carbon atoms, which are bonded to the skeleton via a carbonylamino group (-CO-NH-);
  • Alkynyloxy straight-chain or branched alkynyl groups having 2 to 20 carbon atoms and a double bond in any position;
  • Alkynyloxycarbonyl straight-chain or branched alkynyloxy groups with 2 to 20 carbon atoms, which are bonded to the skeleton via a carbonyl group (-CO-);
  • Alkynylthio straight-chain or branched alkynylthio groups with 2 to 20 carbon atoms
  • Alkynylaminocarbonyl straight-chain or branched alkynyl groups with 2 to 20 carbon atoms, which are bonded to the skeleton via an aminocarbonyl group (-NH-CO-);
  • Cycloalkyl monocyclic alkyl groups with 3 to 12 carbon ring members, for example C 3 -C 8 cycloalkyl such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl and cyclooctyl; Cycloalkoxy: monocyclic alkyl groups with 3 to 8 carbon ring members, which are bonded to the skeleton via an oxy group (-O-); if necessary subst.
  • C 3 -C 8 cycloalkyl such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl and cyclooctyl
  • Cycloalkoxy monocyclic alkyl groups with 3 to 8 carbon ring members, which are bonded to the skeleton via an oxy group (-O-); if necessary subst.
  • Phenyl, phenoxy, phenylthio, phenylcarbonyl or phenylsulfonyl phenyl groups which directly or via an oxy group (-O-), a thio group (-S-), a carbonyl group (-CO-) or a sulfonyl group (-SO 2 -) the backbone are bonded, the phenyl groups each being able to carry one to five halogen atoms and / or one to three of the following radicals: nitro, cyano, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 Alkoxy, C 1 -C 6 haloalkoxy and C 1 -C 6 alkylthio;
  • 5-membered heteroaryl containing one to three nitrogen atoms 5-ring heteroaryl groups which, in addition to carbon atoms, can contain one to three nitrogen atoms as ring members, e.g.
  • 5-membered heteroaryl containing one to three nitrogen atoms or one nitrogen atom and one oxygen or sulfur atom: 5-ring heteroaryl groups which, in addition to carbon atoms, can contain one to four nitrogen atoms or one to three nitrogen atoms and one sulfur or oxygen atom as ring members, and in which two adjacent carbon ring members or a nitrogen and an adjacent carbon ring member may be bridged by a buta-1,3-diene-1,4-diyl group; 5-membered heteroaryl bonded via nitrogen, containing one to four nitrogen atoms, or benzo-fused 5-membered heteroaryl bonded via nitrogen, containing one to three nitrogen atoms: 5-ring heteroaryl groups which, in addition to
  • Carbon atoms can contain one to four nitrogen atoms or one to three nitrogen atoms as ring members, and in which two adjacent carbon ring members or a nitrogen and an adjacent carbon ring member can be bridged by a buta-1,3-diene-1,4-diyl group, where these rings are bound to the framework via one of the nitrogen ring members;
  • 6-membered heteroaryl containing one to three or one to four nitrogen atoms: 6-ring heteroaryl groups, which in addition
  • Carbon atoms may contain one to three or one to four nitrogen atoms as ring members, e.g. 2-pyridinyl, 3-pyridinyl, 4-pyridinyl, 3-pyridazinyl, 4-pyridazinyl, 2-pyrimidinyl, 4-pyrididinyl, 5-pyrimidinyl, 2-pyrazinyl, 1,3,5-triazin-2-yl and 1,2,4-triazin-3-yl;
  • Alkylene divalent unbranched chains from 1 to 10 CH 2 groups, e.g. -CH 2 -, -CH 2 CH 2 -, -CH 2 CH 2 CH 2 -, -CH 2 CH 2 CH 2 CH 2 -, -CH 2 CH 2 CH 2 CH 2 -, -CH 2 CH 2 CH 2 CH 2 CH 2 -, -CH 2 CH 2 CH 2 CH 2 CH 2 - and -CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 -;
  • Alkylenediyl which can contain an oxygen, sulfur or nitrogen atom: divalent unbranched chains from 1 to 10 CH 2 groups, which additionally contain an oxygen (-O-), a sulfur (-S-) or a nitrogen chain link May contain (-NH-), for example the abovementioned alkylene groups and -OCH 2 -, -OCH 2 CH 2 -, -OCH 2 CH 2 CH 2 -, -OCH 2 CH 2 CH 2 CH 2 -, -OCH 2 CH 2 CH 2 CH 2 CH 2 -, -OCH 2 CH 2 CH 2 CH 2 CH 2 -, -OCH 2 CH 2 CH 2 CH 2 CH 2 -,
  • -SCH 2 - -SCH 2 -, -SCH 2 CH 2 -, -SCH 2 CH 2 CH 2 -, -SCH 2 CH 2 CH 2 CH 2 -, -SCH 2 CH 2 CH 2 CH 2 -, -CH 2 SCH 2 -, -CH 2 SCH 2 CH 2 -, -CH 2 SCH 2 CH 2 CH 2 -, -CH 2 SCH 2 CH 2 CH 2 CH 2 -, -CH 2 SCH 2 CH 2 CH 2 CH 2 -, -CH 2 SCH 2 CH 2 CH 2 CH 2 -,
  • -CH CH-CH 2 CH 2 -
  • -CH CH-CH 2 CH 2 CH 2 -
  • -CH CH-CH 2 CH 2 CH 2 -
  • -CH CH-CH 2 CH 2 CH 2 CH 2 -
  • a heterocycle which is bonded next to the nitrogen atom via which it is attached 2 can contain up to 6 carbon ring members or 3 to 5 carbon ring members and 1 or 2 nitrogen, oxygen and / or sulfur ring members, where the ring can be saturated or mono- to trisaturated, for example pyrrolidinyl, isoxazolidinyl, isothiazolidinyl, pyrazolidinyl, oxazolidinyl, thiazolidinyl, Imidazolidinyl, 1,2,4-oxadiazolidinyl, 1,3,4-oxadiazolidinyl, 1,2,4-thiadiazolidinyl
  • 1,3,4-triazolidinyl 2,3-pyrrolinyl, 2, 4-pyrrolinyl, 2,3-isoxazoline, 3,4-isoxazolinyl, 4,5-isoxazolinyl, 2,3-isothiazolinyl, 3,4- Isothiazolinyl, 4,5-isothiazolinyl, 2,3-dihydropyrazolyl, 3,4-dihydropyrazolyl, 4,5-dihydropyrazolyl, 2,3-dihydrooxazolyl, 3,4-dihydrooxazolyl, imidazolyl, 1,2,4-oxadiazolyl, 1, 2,4-thiadiazolyl, 1,2,4-triazolyl, 1,3,4-oxadiazolyl, 1,3,4-thiadiazolyl, 1,3,4-triazolyl, piperidinyl, tetrahydropyridazinyl, tetrahydropyridid
  • Phenyl Preferred in view of the biological effectiveness of the
  • Herbicidal compositions are mixtures that contain one or more
  • C 1 -C 12 alkyl preferably C 1 -C 10 alkyl, in particular C 2 -C 8 alkyl, C 3 -C 7 cycloalkyl, preferably C 3 -C 6 cycloalkyl, C 2 -C 8 alkenyl , preferably C 3 -C 6 alkenyl, in particular C 3 -C 5 alkenyl, or
  • C 3 -C 4 alkynyl where these groups can carry one or more halogen atoms, preferably fluorine and / or chlorine and / or one or two of the following radicals:
  • C 1 -C 4 alkylsulfonyl preferably C 1 -C 2 alkylsulfonyl, in particular methylsulfonyl,
  • Phenyl-C 1 -C 4 -alkoxy preferably benzyloxy, 1-phenyl-et hoxy and 2-phenylethoxy
  • Phenyl-C 1 -C 4 -alkoxycarbonyl preferably benzyloxycarbonyl, phenoxy-C 1 -C 4 -alkoxy, preferably phenoxy-C 1 -C 3 -alkoxy, in particular phenoxymethoxy, 1-phenoxy et hoxy, 2-phenoxypropyloxy and 2 -Phenoxyethoxy,
  • Phenoxy-C 1 -C 4 -alkoxycarbonyl 1 where the phenyl radicals of the groups mentioned above can in turn carry one or more of the following radicals:
  • Halogen preferably fluorine and chlorine
  • C 1 -C 2 alkyl preferably methyl
  • R d is hydrogen, C 1 -C 3 alkyl, preferably methyl, ethyl and n-propyl, or phenyl, which can carry one or more of the following groups:
  • Halogen preferably fluorine and chlorine
  • C 1 -C 2 alkyl preferably methyl
  • agents are preferred in terms of biological activity which contain one or more compounds Ila and / or Ilb in which X a is hydrogen,
  • Halogen preferably fluorine and chlorine, C 1 -C 2 alkyl, preferably methyl, C 1 -C 2 alkoxy, preferably methoxy, C 1 -C 2 haloalkyl, preferably trifluoromethyl
  • Y 'halogen preferably chlorine, C 1 -C 2 alkyl, preferably methyl, C 1 -C 2 alkoxy, preferably methoxy, C 1 -C 2 haloalkyl, preferably trifluoromethyl mean.
  • agents which contain one or more compounds Ila and / or Ilb in which
  • Halogen preferably fluorine and chlorine, in particular
  • Chlorine or C 1 -C 2 haloalkyl, preferably C 1 haloalkyl,
  • Agents containing one or more compounds of the formula Ila are very particularly preferred, the variables having the following meanings:
  • Halogen preferably chlorine, C 1 -C 4 haloalkyl, preferably trifluoromethyl, a 1 to 3; Z 'OR c ;
  • R c is hydrogen, C 1 -C 8 alkyl, preferably C 1 -C 5 alkyl, in particular
  • C 1 -C 4 alkyl, or C 3 -C 7 cycloalkyl, preferably C 3 -C 6 cycloalkyl, these radicals carrying one or more halogen atoms, preferably fluorine and chlorine and / or one or two of the following groups can:
  • C 1 -C 4 alkoxycarbonyl preferably C 1 -C 2 alkoxycarbonyl, C 2 -C 6 alkenyloxycarbonyl, in particular allyloxycarbonyl, C 2 -C 6 alkynyloxycarbonyl, in particular propargyloxycarbonyl,
  • R d is hydrogen or C 1 -C 4 alkyl, preferably methyl, ethyl, isopropyl and t-butyl, or two substituents R d in adjacent positions together are C 4 -C 5 alkylene,
  • R g is hydrogen
  • C 1 -C 8 alkyl preferably C 1 -C 4 alkyl, especially methyl, ethyl, n-propyl, isopropyl and t-butyl, C 1 -C 6 haloalkyl, preferably C 1 -C 4 - Haloalkyl, especially trifluoromethyl and trichloromethyl,
  • C 3 -C 7 cycloalkyl in particular cyclopropyl, cyclopentyl and cyclohexyl, or phenyl and
  • R h is hydrogen, C 1 -C 8 alkyl, preferably C 1 -C 4 alkyl, in particular methyl and ethyl, C 1 -C 8 haloalkyl, in particular C 1 -C 2 haloalkyl, C 1 -C 4 alkoxy -C 1 -C 4 alkyl, C 1 -C 6 hydroxyalkyl, C 3 -C 7 cycloalkyl, especially cyclopropyl, or tri- (C 1 -C 4 alkyl) silyl, especially trimethylsilyl, triethylsilyl, t- Butyldimethylsilyl and triisopropylsilyl.
  • Agents which contain compounds of the formula IIb are furthermore preferred, the variables having the following meaning:
  • Y 'halogen preferably fluorine and chlorine, especially chlorine, or C 1 -C 4 haloalkyl, preferably C 1 -C 2 haloalkyl, especially trifluoromethyl, b 1 to 3;
  • R c is hydrogen, C 1 -C 8 alkyl, C 1 -C 8 -haloalkyl, preferably C 1 -C 4 -haloalkyl, in particular 2,2,2-trifluoroethyl.
  • C 1 -C 4 alkyl or C 3 -C 6 alkenyl which can carry one to three of the following radicals: carboxy, halogen, C 1 -C 4 alkoxy and / or C 1 -C 4 alkoxycarbonyl.
  • R 1 is hydrogen, -OR 6 or -O m -NR 7 R 8 , where
  • R 6 is hydrogen, an alkali metal cation, the equivalent of an alkaline earth metal cation or an organic ammonium ion; C 1 -C 10 alkyl, which can carry one to five halogen atoms and / or one of the following radicals: cyano, C 1 -C 4 alkoxy,
  • C 1 -C 4 alkylthio, C 1 -C 8 alkylcarbonyl, C 1 -C 8 alkoxycarbonyl, C 3 -C 12 cycloalkyl, -ON CR 10 R 11 , phenyl, phenoxy and phenylcarbonyl, where the aromatic rings in turn one to five halogen atoms and / or one to three of the following radicals can carry: C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy and C 1 -C 4 alkylthio;
  • C 1 -C 10 alkyl which can carry one to five halogen atoms and carries one of the following radicals: 5-membered heteroaryl, containing one to three nitrogen atoms, which can carry one to four halogen atoms and / or one or two of the following radicals: C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy,
  • C 2 -C 6 alkyl which carries one of the following radicals in the 2-position: C 1 -C 6 alkoxyimino, C 3 -C 6 alkenyloxyinu.no, C 3 -Cg haloalkenyloxyimino or benzyloxyimino; C 3 -C 6 alkenyl or C 3 -C 6 alkynyl, these radicals in turn being able to carry one to five halogen atoms;
  • Phenyl which can carry one to five halogen atoms and / or one to three of the following radicals: C 1 -C 4 alkyl and
  • R 7 , R 8 are hydrogen
  • C 1 -C 6 alkyl or C 3 -C 6 alkenyl which can carry one to five halogen atoms and / or one or two of the following radicals: C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 1 -C 6 alkylcarbonyl, C 1 -C 6 alkoxycarbonyl, di-C 1 -C 6 alkylamino and C 3 -C 6 cycloalkyl; if necessary subst. Phenyl;
  • R 7 and R 8 together are C 3 -C 7 -alkylene diyl, which may contain an oxygen, sulfur or nitrogen atom, and which may carry one to three C 1 -C 4 -alkyl radicals; means.
  • R 2 is chlorine, C 1 -C 2 alkyl, C 1 -C 2 haloalkyl, C 1 -C 2 alkoxy and Ci-C 2 haloalkoxy.
  • R 3 is chlorine, C 1 -C 2 alkyl, C 1 -C 2 haloalkyl, C 1 -C 2 alkoxy and
  • Chlorine for C 1 -C 2 alkyl or C 1 -C 2 alkoxy, these groups bearing one of the following radicals:
  • 5-membered heteroaryl containing one to four nitrogen atoms or one to three nitrogen atoms and one sulfur or oxygen atom which can carry one to three halogen atoms and / or one to three of the following radicals:
  • 6-membered heteroaryl containing one to three nitrogen atoms which can carry one to three halogen atoms and / or one to three of the following radicals: C 1 -C 2 -alkyl,
  • C 1 -C 2 alkylthio and C 1 -C 2 haloalkyl for subst. Phenyl or phenoxy; for 5-membered heteroaryl containing one to four nitrogen atoms or one to three nitrogen atoms and one oxygen or sulfur atom which can carry one to three halogen atoms and / or one to three of the following radicals: C 1 -C 2 -alkyl,
  • R 1 is hydrogen
  • R 2 , R 3 are C 1 -C 4 alkyl, preferably C 1 -C 2 alkyl, C 1 -C 4 alkoxy, preferably C 1 -C 2 alkoxy, C 1 -C 4 haloalkyl, in particular trifluoromethyl, C 1 -C 4 haloalkoxy, preferably C 1 -C 2 haloalkoxy, especially difluoromethoxy, trifluoromethoxy and trichloromethoxy, C 1 -C 4 alkylthio, preferably C 1 -C 2 alkylthio, especially methylthio,
  • R 5 is hydrogen; C 1 -C 4 alkyl, C 3 -C 6 alkenyl, preferably C 3 -C 4 alkenyl, in particular 2-propen-1-yl, 3-buten-1-yl and 3-buten-2-yl, or C 3 -C 6 alkynyl, preferably C 3 -C 4 alkynyl, in particular
  • Halogen preferably fluorine and chlorine, especially chlorine - C 1 -C 4 alkoxy, preferably C 1 -C 2 alkoxy,
  • R 6 is hydrogen, an alkali metal cation, preferably sodium, potassium or lithium, the equivalent of an alkaline earth metal cation or an organic ammonium ion,
  • C 1 -C 10 alkyl preferably C 1 -C 5 alkyl, in particular
  • C 1 -C 3 alkyl which can carry one to five halogen atoms, preferably fluorine and chlorine and / or one of the following radicals:
  • Halogen preferably fluorine or chlorine
  • C 1 -C 4 alkyl preferably C 1 -C 2 alkyl
  • - C 1 -C 4 -haloalkyl preferably C 1 -C 2 -haloalkyl, in particular trifluoromethyl or difluoromethyl, - C 1 -C 4 alkoxy, preferably C 1 -C 2 -alkoxy, in particular methoxy,
  • C 1 -C 4 haloalkoxy preferably C 1 -C 2 haloalkoxy, in particular trifluoromethoxy
  • halogen atoms preferably fluorine or chlorine, that the total number of the radicals is 4 or 5;
  • C 1 -C 10 alkyl preferably C 1 -C 6 alkyl, in particular C 1 -C 4 alkyl, which can carry one to five halogen atoms, preferably fluorine or chlorine, and carries a 5-membered heteroaryl radical which
  • Halogen preferably fluorine or chlorine
  • C 1 -C 4 alkyl preferably C 1 -C 2 alkyl, C 1 -C 4 haloalkyl, preferably C 1 -C 2 haloalkyl,
  • C 1 -C 4 alkylthio preferably C 1 -C 2 alkylthio and, if desired, as many halogen atoms, preferably fluorine or chlorine, as further substitutable ring members are present;
  • C 2 -C 6 alkyl which carries one of the following radicals in the 2-position:
  • C 3 -C 6 alkenyl preferably C 3 -C 4 alkenyl, in particular alkyl and but-3-en-1-yl, or C 3 -C 6 alkynyl, preferably
  • C 3 -C 4 alkynyl in particular propargyl or but-3-yn-1-yl, these radicals in turn being able to carry one to five, preferably one to three, halogen atoms, in particular fluorine and / or chlorine;
  • Halogen preferably fluorine or chlorine
  • C 1 -C 4 alkyl preferably C 1 -C 3 alkyl, in particular methyl or ethyl,
  • C 1 -C 6 alkyl preferably C 1 -C 5 alkyl, in particular
  • C 1 -C 4 alkyl C 3 -C 6 ⁇ alkenyl, preferably C 3 -C 4 alkenyl, especially allyl, or C 3 -C 6 alkynyl, preferably C 3 -C 4 alkynyl, in particular propargyl, which can carry one or two of the following substituents:
  • Halogen preferably fluorine or chlorine
  • C 1 -C 6 alkylthio preferably C 1 -C 3 alkylthio, in particular methylthio
  • C 1 -C 6 haloalkoxy preferably C 1 -C 2 haloalkoxy, in particular trifluoromethoxy, trichloromethoxy or 2,2,2-trichloroethyl,
  • - C 1 -C 6 alkylcarbonyl preferably C 1 -C 3 alkylcarbonyl, - C 3 -C 6 alkenylcarbonyl, preferably C 3 -C 4 alkenylcarbonyl, - C 1 -C 6 alkoxycarbonyl, preferably C 1 -C 3 ⁇ alkoxycarbonyl, in particular C 1 -C 2 alkoxycarbonyl,
  • R 7 and R 8 together are preferably C 3 -C 7 -alkylenediyl, which may contain an oxygen, sulfur or nitrogen atom
  • R 9 is C 1 -C 6 alkyl, preferably C 1 -C 4 alkyl, in particular methyl and ethyl, which can carry one to four of the following radicals: nitro, cyano and / or halogen, preferably halogen, in particular fluorine or chlorine;
  • Phenyl which can carry one to four of the following radicals: nitro, cyano, halogen, preferably fluorine and chlorine, and / or C 1 -C 6 alkyl, preferably C 1 -C 3 alkyl, in particular methyl;
  • R 10 , R 11 are C 1 -C 10 alkyl, preferably C 1 -C 6 alkyl,
  • C 1 -C 4 alkyl which is a phenyl radical, a C 1 -C 4 alkoxy group, in particular methoxy, and / or a
  • C 1 -C 4 alkylthio group especially methylthio; C 1 -C 6 alkoxy, in particular C 1 -C 4 alkoxy, or
  • R 10 and R 11 together are C 3 -C 12 -alkylenediyl, preferably
  • C 4 -C 12 alkenylenediyl preferably C 5 -C 7 alkenylenediyl, which can carry a phenyl radical or one to five, preferably one to three, C 1 -C 4 alkyl groups, in particular methyl, ethyl and t-butyl, and which if desired, can be bridged by a C 1 -C 4 alkylene chain, preferably C 1 -C 2 alkylene, in particular methylene;
  • R 12 is C 1 -C 6 alkyl, preferably C 1 -C 4 alkyl, C 3 -C 6 alkenyl, in particular C 3 -C 4 alkenyl, or C 3 -C 6 alkynyl, in particular C 3 -C 4 -alkynyl,
  • R 13 is hydrogen
  • Alkyl preferably C 1 -C 4 alkyl, in particular methyl, ethyl, n-propyl, iso-propyl, n-butyl and iso-butyl, which can carry the following radicals: hydroxy, amino, hydrogen sulfide, alkylthio, carboxy, carbamoyl , Guanidinyl, phenyl, hydroxyphenyl, imidazolyl or indolyl; or
  • R 13 and R 7 together alkylenediyl, preferably C 3 -C 4 -alkylenediyl, m 0 or 1, n 0, 1 or 2, preferably 0 or 2, p 0, 1 or 2, preferably 2,
  • - 5-membered heteroaryl containing one to four nitrogen atoms or one to three nitrogen atoms and one sulfur or oxygen atom which can carry one to three, preferably one or two, halogen atoms, in particular fluorine and chlorine and / or one to three of the following radicals : Nitro, cyano, C 1 -C 4 alkyl, preferably C 1 -C 3 alkyl, in particular C 1 -C 2 alkyl, C 1 -C 4 alkoxy, preferably C 1 -C 3 alkoxy, in particular C 1 -C 2 alkoxy, C 1 -C 4 alkylthio, especially methylthio, C 1 -C 4 haloalkyl, especially trifluoromethyl and trichloromethyl, or phenyl, which in turn can carry one to three halogen atoms, preferably chlorine and / or methyl groups, or
  • 6-membered heteroaryl containing one to three, preferably one or two, nitrogen atoms which can carry one to three, preferably one or two, halogen atoms, in particular fluorine and chlorine and / or one to three of the following radicals: nitro, cyano, C 1 -C 4 alkyl, preferably C 1 -C 3 alkyl, in particular C 1 -C 2 alkyl, trifluoromethyl and trichloromethyl, C 1 -C 4 alkylthio, in particular methylthio and / or C 1 -C 4 haloalkyl , preferably difluoromethyl, trifluoromethyl and trichloromethyl; possibly . subst. Phenyl or phenoxy;
  • 5-membered heteroaryl containing one to four nitrogen atoms or one to three nitrogen atoms and one oxygen or sulfur atom, preferably pyrrolyl, pyrazolyl,
  • Halogen preferably fluorine, chlorine or bromine, especially chlorine
  • C 1 -C 4 alkylthio preferably C 1 -C 2 alkylthio, in particular methylthio
  • C 1 -C 4 haloalkyl preferably C 1 -C 3 haloalkyl, in particular difluoromethyl, trifluoromethyl or trichloromethyl,
  • phenyl which in turn can carry one to three halogen atoms, in particular fluorine or chlorine, and / or one to three methyl groups;
  • halogen atoms preferably fluorine, chlorine or bromine atoms, in particular chlorine atoms, as are further substitutable ring members; benzo-fused 5-membered heteroaryl containing one to three nitrogen atoms or one nitrogen atom and one oxygen or sulfur atom, preferably indole, benzimidazole, benzoxazole and benzothiazole, which can carry one to three of the following radicals:
  • Halogen preferably chlorine
  • Halogen preferably chlorine or bromine, in particular
  • halogen atoms preferably chlorine or bromine atoms, in particular chlorine atoms, that the total number of substituents is 4;
  • Benzothienyl or benzofuryl both of which can carry a halogen atom, in particular chlorine, and / or one of the following radicals:
  • C 1 -C 4 alkyl preferably C 1 -C 2 alkyl, in particular methyl
  • R 1 for -OR 6 or -O m -NR 7 R 8 ;
  • R 6 is hydrogen, an alkali metal cation, preferably lithium, sodium and potassium, the equivalent of an alkaline earth metal cation or a
  • Halogen preferably fluorine or chlorine
  • R 7 , R 8 for hydrogen or
  • C 1 -C 6 alkyl preferably C 1 -C 6 alkyl, in particular
  • C 3 -C 7 -alkylenediyl which may contain an oxygen, sulfur or nitrogen atom, preferably C 3 -C 6 -alkylenediyl, in particular C 4 -C 5 -alkylenediyl and ethyleneoxyethylene, and which has one to three C 1 -C 4 alkyl radicals, preferably C 1 -C 2 alkyl, in particular one to two methyl groups; R 10 , R 11 for C 1 -C 10 alkyl, preferably C 1 -C 6 alkyl, in particular
  • C 5 -C 7 -alkylenediyl which can carry a phenyl radical or one to five C 1 -C 3 -alkyl groups, preferably methyl, ethyl and t-butyl; m for 1;
  • R for chlorine, if necessary subst.
  • Phenyl for 5-membered heteroaryl containing one to four nitrogen atoms or one to three nitrogen atoms and one oxygen or sulfur atom, preferably pyrrolyl, pyrazolyl, imidazolyl,
  • heteroaromatics can, if desired, carry one to three of the following radicals: halogen, preferably fluorine or chlorine,
  • C 1 -C 4 alkoxy preferably C 1 -C 3 alkoxy, in particular methoxy or ethoxy
  • C 1 -C 4 alkylthio preferably C 1 -C 2 alkylthio, in particular methylthio
  • C 1 -C 4 haloalkyl in particular difluoromethyl, trifluoromethyl or trichloromethyl, and, if desired, additionally as many halogen atoms, preferably fluorine or chlorine atoms, as are further substitutable ring members; Thienyl or furyl, which can carry one to three halogen atoms, preferably fluorine or chlorine, and / or C 1 -C 4 alkyl radicals, preferably methyl or ethyl.
  • 1,2,4-triazole-3-carboxylic acid ethyl ester (fenchlorazole) and related compounds (see e.g. EP-A 174 562 and
  • the safeners (antidots) from groups a) to f) above reduce or prevent phytotoxic effects which can occur when herbicides Ia and Ib are used in crops without impairing the effectiveness of these herbicides against harmful plants.
  • the area of application of conventional crop protection agents can be expanded considerably and e.g. to be extended to crops such as wheat, barley, maize and other Gramineae crops in which use of the herbicides has hitherto not been possible or has been possible only to a limited extent, that is to say in low doses with little broad effect.
  • the herbicidal active ingredients and the safeners mentioned can be applied together (as a finished formulation or in a tank mix process) or in succession in any order.
  • the weight ratio of safener: herbicide can vary within wide limits and is preferably in the range from 1:10 to 1: 0.1, in particular from 1:10 to 1: 0.2.
  • the optimal amounts of herbicide and safener depend on the type of herbicide or safener used and on the type of crop to be treated and can be determined on a case-by-case basis by means of appropriate preliminary tests.
  • the main areas of application for the use of safeners are primarily cereal crops (wheat, rye, barley, oats), rice, maize, sorghum, but also cotton or soybeans, preferably cereals and maize.
  • the safeners of type Ila and Ilb can be used for pretreating the seed of the crop (dressing the seeds) or introduced into the seed furrows before sowing or used together with the herbicide before or after emergence of the plants.
  • Pre-emergence treatment includes both the treatment of the cultivated area before sowing and the treatment of the sown but not yet overgrown cultivated areas.
  • Co-application with the herbicide by post-emergence is preferred.
  • Tank mixes or ready formulations can be used for this.
  • the method with the joint use of herbicide and safener in the post-emergence process represents a significant practical advantage.
  • the farmer saves substantial costs by one step of the common application and, above all, does not have to labor-intensive seeds Carry out staining, which requires a special pickling device.
  • the work involved in the additional application of the safener is practically negligible, especially when herbicide and safener are used and applied as a finished formulation.
  • the 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 0.5 kg, of active compound per hectare.
  • the present invention therefore also relates to a process for protecting crop plants from phytotoxic side effects of herbicides of the types Ia and Ib mentioned, which is characterized in that an effective amount of a compound of the formula Ila or Ilb mentioned before, after or simultaneously with the herbicide of the above-mentioned types Ia and Ib, preferably together with the herbicide of types Ia and Ib in the post-emergence process, to which plants, plant seeds or the area under cultivation is applied.
  • the compounds of type Ila and Ilb and their combinations with one or more of the herbicides mentioned can be formulated in various ways, depending on which biological and / or chemical-physical parameters are specified. Possible formulation options are, for example: wettable powder (WP), emulsifiable concentrates (EC), water-soluble powders (SP), water-soluble concentrates (SL), concentrated emulsions (EW) such as oil-in-water and water-in-oil emulsions, sprayable solutions or emulsions, capsule suspensions (CS) oil or water-based dispersions (SC), suspoemulsions, suspension concentrates, dusts (DP), oil-miscible solutions (OL), mordants, granules (GR) in the form of micro, spray, elevator - and adsorption granules, granules for soil and litter application, water-soluble granules (SG), water-dispersible granules (WG), ULV formulations, microcapsules and waxes
  • the necessary formulation auxiliaries such as inert materials, surfactants, solvents and other additives are also known and are described, for example, in: Watkins,
  • combinations with other pesticidally active substances, fertilizers and / or growth regulators can also be produced, e.g. in the form of a finished formulation or as a tank mix.
  • Spray powders are preparations which are uniformly dispersible in water and which, in addition to the active substance, contain wetting agents, e.g. polyoxethylated alkylphenols, polyoxethylated fatty alcohols and fatty amines, fatty alcohol polyglycol ether sulfates, alkanesulfonates or alkylarylsulfonates and dispersants, e.g. sodium lignosulfonate, 2,2, -dinaphthylmethane-6,6'-disulfonic acid sodium, dibutylnaphthalenesulfonic acid sodium or oleylmethyl tauric acid sodium.
  • wetting agents e.g. polyoxethylated alkylphenols, polyoxethylated fatty alcohols and fatty amines, fatty alcohol polyglycol ether sulfates, alkanesulfonates or alkylarylsulfonates and dispersants,
  • Emulsifiable concentrates are made by dissolving the active ingredient in an organic solvent, e.g. Butanol, cyclohexanone, dimethylformamide, xylene or higher-boiling aromatics or hydrocarbons with the addition of one or more emulsifiers.
  • organic solvent e.g. Butanol, cyclohexanone, dimethylformamide, xylene or higher-boiling aromatics or hydrocarbons.
  • emulsifiers for example
  • alkylarylsulfonic acid calcium salts such as calcium dodecylbenzenesulfonate or nonionic emulsifiers such as fatty acid polyglycol esters, alkylaryl polyglycol ethers, fatty alcohol polyglycol ethers, propylene oxide-ethylene oxide condensation products (e.g.
  • Block polymers alkyl polyethers, sorbitan fatty acid esters, polyoxymethylene sorbitan fatty acid esters or polyoxethylene sorbitol esters.
  • Dusts are obtained by grinding the active ingredient with finely divided solid substances, e.g. Talc, natural clays such as kaolin, bentonite and pyrophylite, or diatomaceous earth.
  • finely divided solid substances e.g. Talc, natural clays such as kaolin, bentonite and pyrophylite, or diatomaceous earth.
  • Granules can either be produced by spraying the active ingredient onto adsorbable, granulated inert material or by applying active ingredient concentrates by means of adhesives, for example polyvinyl alcohol, sodium polyacrylic acid or mineral oils, to the surface of carriers such as sand, kaolinite or granulated inert material.
  • adhesives for example polyvinyl alcohol, sodium polyacrylic acid or mineral oils
  • Suitable active ingredients can also be used in the manufacture of fertilizer granules usual way - if desired in a mixture with fertilizers - granulated.
  • the application rates of the herbicides Ia or Ib can vary within wide limits and are generally in the range from 0.001 to 10 kg, preferably 0.005 to 3 kg, in particular 0.01 to 0.5 kg of active ingredient per hectare .
  • the agrochemical preparations generally contain 0.1 to 99% by weight, in particular 0.1 to 95% by weight, of substances of the type Ila or Ilb or of the antidote / herbicide / active substance mixture Ia or Ib and 1 to 99.9% by weight .-%, in particular 5 to 99.8% by weight, of a solid or liquid additive and 0 to 25% by weight, in particular 0.1 to 25% by weight, of a surfactant.
  • the active substance concentration in wettable powders is e.g. about 10 to 90 wt .-%, the rest of 100 wt .-% consists of conventional formulation components.
  • the active substance concentration is approximately 1 to 80% by weight of active substances.
  • Dust-like formulations contain about 1 to 20% by weight of active ingredients, sprayable solutions about 0.2 to 20% by weight of active ingredients.
  • the active ingredient content depends in part on whether the active compound is in liquid or solid form. As a rule, the content of the water-dispersible granules is between 10 and 90% by weight.
  • the active ingredient formulations mentioned may contain the customary adhesives, wetting agents, dispersants, emulsifiers, penetrants, solvents, fillers or carriers.
  • the formulations present in commercially available form are optionally diluted in the customary manner, for example in the case of wettable powders, emulsifiable concentration, dispersions and water-dispersible granules, using water. Dust-like preparations, granules and sprayable solutions are usually no longer diluted with other inert substances before use.
  • Particularly good efficacies of the agents according to the invention can be achieved if, in addition to the surfactants contained in the formulations, further wetting agents in concentrations of 0.1 to 0.5% by weight are added in a tank mix process, for example nonionic wetting agents or Wetting agents of the fatty alcohol polyol ether sulfate type (see, for example, DE-A 40 29 304).
  • the amount of "safener" required varies. The following examples serve to explain the invention:
  • a suicide is obtained by adding 10 parts by weight of a compound of type Ila or Ilb or an active ingredient mixture of a herbicide of type Ia or Ib and a safener of type Ila or Ilb and 90% by weight. - Mix parts of talc as an inert substance and crush them in a hammer mill.
  • a wettable powder which is readily dispersible in water is obtained by adding 25 parts by weight of a compound of type Ila or Ilb or an active ingredient mixture of a herbicide of type Ia or Ib and a safener of type Ila or Ilb, 64 parts by weight of quartz containing kaolin as an inert substance, 10 parts by weight of potassium lignosulfonate and 1 part by weight sodium oleoylmethyl taurine as a wetting and dispersing agent are mixed and ground in a pin mill.
  • a dispersion concentrate which is easily dispersible in water is obtained by mixing 20 parts by weight of a compound of type Ila or Ilb or an active substance mixture of a herbicide of type Ia or Ib and one
  • Type Ila or Ilb safener 6 parts by weight of alkylphenol polyglycol ether ( A Triton X 207), 3 parts by weight of isotridecanol polyglycol ether (8 EO) and 71 parts by weight of paraffinic mineral oil (boiling range, for example, about 255 to over 277 ° C) mixes and ground in a attritor to less than 5 microns.
  • alkylphenol polyglycol ether A Triton X 207
  • isotridecanol polyglycol ether 8 EO
  • paraffinic mineral oil 71 parts by weight of paraffinic mineral oil (boiling range, for example, about 255 to over 277 ° C) mixes and ground in a attritor to less than 5 microns.
  • An emulsifiable concentrate is obtained from 15 parts by weight of a compound of type Ila or Ilb or a mixture of active ingredients from a herbicide of type Ia or Ib and a safener of type Ila or Ilb, 75 parts by weight of cyclohexanone Solvent and 10 parts by weight of oxyethylated nonylphenol as an emulsifier.
  • a water-dispersible granulate is obtained by
  • Type Ila or Ilb 10 parts by weight of calcium lignosulfonic acid
  • a water-dispersible granulate is also obtained by
  • test plants were first grown to a height of 3 to 20 cm, depending on the growth habit, and only then treated.
  • the herbicidal compositions were suspended or emulsified in water as a distribution agent and sprayed by means of finely distributing nozzles.
  • the antidote compounds were prepared for the post-emergence treatment in a mixture consisting of 80% cyclohexanone and 20% Emulphor ® EL * ) with 10% (% by weight) of active ingredient.
  • test vessels were set up in the greenhouse, 18 to 30 ° C. being preferred for heat-loving species and 10 to 25 ° C. being preferred for those with moderate climates.
  • the trial period spans 3 to 5 weeks. During this time, the plants were cared for and their response to the individual treatments was recorded.
  • the damage caused by the chemical agents was assessed on a scale from 0 to 100% compared to the untreated control plants. 0 means no damage and 100 means complete destruction of the plants.
  • Emulan® EL emulsifier based on ethoxylated fatty alcohols
  • the example antidotic compounds markedly improve the tolerance of the herbicides 1,021 and 2,044 for crop plants belonging to the family of gramineae (grasses).

Abstract

Un herbicide contient a) un ou plusieurs dérivés herbicides d'acide salicylique correspondant aux formules (Ia) ou (Ib), dans laquelle Z désigne =N- et =CH-; Y désigne -O-, -S- et -NR4-; X désigne =O, =N-R?5, =NO-R5¿, =N-NH-R5, et =N-N(R5)2; R1 désigne H, succinyliminooxy, alkyle, alkylcarbonyle, alcoxycarbonyle, hétéroaryle éventuellement substitué, -OR6, -Om-NR7R8, -NH-SO¿2?-R?9; R2, R3¿ désignent halogène, alkyle, alkyle halogène, alcoxy, alcoxy halogène, alkylthio, alkylamino et dialkylamino; R désigne Cl, alkyle éventuellement substitué, alcényle, alcinyle, alcoxy, alkylthio, alkylsufonyle, phényle, phénoxy, phénylthio, phénylsulfonyle, hétéroaryle, naphtyle, quinolinyle, quinazolinyle ou -C(=X')-R1'; R' désigne H ou R' et R désignent ensemble 1,3-butadiène-1,4-yl; A désigne =N-, =N(←O)- ou =CR''-. Cet herbicide contient également b) un ou plusieurs composés ayant les formules (IIa) ou (Iib), dans lesquelles Xa désigne H, NO¿2?, halogène, alkyle, alcoxy, alkyle halogènalkyle; Y' désigne NO2, halogène, alkyle, alcoxy, halogène alkyle; R?a¿ désigne alkylène éventuellement substitué; Z' désigne Or?c, Src ou NRcRb; Rb¿ désigne hydrogène, alkyle, alcoxy, phényle éventuellement substitué ou Rb et Rc désignent ensemble avec l'atome de N auquel ils sont liés hétérocyclyle éventuellement substitué; Rc désigne H, alkyle éventuellement substitué, cycloalkyle, alcényle, alkinyle; a vaut 1 à 5; b vaut 1 à 5; W désigne un hétérocyclyle bivalent à 5 membres représenté par les formules (W1) à (W4). L'invention concerne également un procédé d'utilisation de cet herbicide.
PCT/EP1994/000862 1993-03-30 1994-03-18 Herbicides contenant une ou plusieurs substances actives herbicides du groupe des derives d'acide salicylique et un ou plusieurs composes antidotes WO1994022310A1 (fr)

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AU64280/94A AU6428094A (en) 1993-03-30 1994-03-18 Herbicides containing one or several herbicidal active substances from the group of the salicylic acid derivates and one or several antidote compounds

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DEP4310220.4 1993-03-30
DE4310220A DE4310220A1 (de) 1993-03-30 1993-03-30 Herbizide Mittel, enthaltend einen oder mehrere herbizide Wirkstoffe aus der Gruppe der Salizylsäurederivate und ein oder mehrere antidotisierend wirkende Verbindungen

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WO1995007266A1 (fr) * 1993-09-04 1995-03-16 Basf Aktiengesellschaft Derives d'acide lactique substitues comportant un reste organique n en position beta, leur preparation et leur utilisation comme herbicides et comme antidotes
EP0652216A3 (fr) * 1993-11-02 1995-05-17 BASF Aktiengesellschaft Dérivés d'aldéhyde salicylique et d'acide salicylique de pyridine, procédés pour leur préparation et leur utilisation comme herbicides
EP0656357A1 (fr) * 1993-11-02 1995-06-07 BASF Aktiengesellschaft Dérivés d'aldéhyde salicylique et d'acide salicylique de pyridine-N-oxide, procédés pour leur préparation et leur utilisation comme herbicides
US11510617B2 (en) 2012-08-02 2022-11-29 Accuvein, Inc. Device for detecting and illuminating the vasculature using an FPGA

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AU6209098A (en) * 1997-01-15 1998-08-07 Novartis Ag Herbicidal agent

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EP0521407A1 (fr) * 1991-06-29 1993-01-07 Hoechst Schering AgrEvo GmbH Nouveaux mélanges d'herbicides et d'antidotes
WO1994000987A2 (fr) * 1992-07-08 1994-01-20 Ciba-Geigy Ag Composition herbicide selective

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EP0521407A1 (fr) * 1991-06-29 1993-01-07 Hoechst Schering AgrEvo GmbH Nouveaux mélanges d'herbicides et d'antidotes
WO1994000987A2 (fr) * 1992-07-08 1994-01-20 Ciba-Geigy Ag Composition herbicide selective

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CIBA-GEIGY: "Neue Seklektiv-herbizide Mittel", RESEARCH DISCLOSURE, vol. 357, no. 25, January 1994 (1994-01-01), HAVANT GB, pages 33 - 45 *

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1995007266A1 (fr) * 1993-09-04 1995-03-16 Basf Aktiengesellschaft Derives d'acide lactique substitues comportant un reste organique n en position beta, leur preparation et leur utilisation comme herbicides et comme antidotes
EP0652216A3 (fr) * 1993-11-02 1995-05-17 BASF Aktiengesellschaft Dérivés d'aldéhyde salicylique et d'acide salicylique de pyridine, procédés pour leur préparation et leur utilisation comme herbicides
EP0656357A1 (fr) * 1993-11-02 1995-06-07 BASF Aktiengesellschaft Dérivés d'aldéhyde salicylique et d'acide salicylique de pyridine-N-oxide, procédés pour leur préparation et leur utilisation comme herbicides
US5627136A (en) * 1993-11-02 1997-05-06 Basf Aktiengesellschaft Pyridine-N-oxide-substituted salicylaldehyde or salicyclic acid derivatives, their preparation and their use as herbicides
US5783521A (en) * 1993-11-02 1998-07-21 Basf Aktiengesellschaft Substituted pyridylsalicylaldehyde or -salicylic acid derivatives, their preparation and their use as herbicides
US11510617B2 (en) 2012-08-02 2022-11-29 Accuvein, Inc. Device for detecting and illuminating the vasculature using an FPGA

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DE4310220A1 (de) 1994-10-06
IL109140A0 (en) 1994-06-24

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