EP0671880A1 - Composition herbicide selective - Google Patents

Composition herbicide selective

Info

Publication number
EP0671880A1
EP0671880A1 EP93915750A EP93915750A EP0671880A1 EP 0671880 A1 EP0671880 A1 EP 0671880A1 EP 93915750 A EP93915750 A EP 93915750A EP 93915750 A EP93915750 A EP 93915750A EP 0671880 A1 EP0671880 A1 EP 0671880A1
Authority
EP
European Patent Office
Prior art keywords
alkyl
hydrogen
alkoxy
phenyl
halogen
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Withdrawn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
EP93915750A
Other languages
German (de)
English (en)
Inventor
Jutta Glock
Elmar Kerber
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.)
Novartis AG
Original Assignee
Ciba Geigy 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 Ciba Geigy AG filed Critical Ciba Geigy AG
Publication of EP0671880A1 publication Critical patent/EP0671880A1/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Withdrawn legal-status Critical Current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 present invention relates to a selective herbicidal composition for controlling grasses and weeds in crops of useful plants, especially in cereal crops, which comprises a herbicide and a safener (antidote) which protects the useful plants, but not the weeds, from the phytotoxic action of the herbicide, and to the use of that composition or of the combination of herbicide and safener in the control of weeds in crops of useful plants.
  • a herbicide and a safener (antidote) which protects the useful plants, but not the weeds, from the phytotoxic action of the herbicide, and to the use of that composition or of the combination of herbicide and safener in the control of weeds in crops of useful plants.
  • EP-A-0094349 discloses quinoline derivatives that protect crop plants from the phytotoxic action of herbicides of specific classes of compounds, such as phenoxy- propionic acid ester herbicides, ureas, carbamates or diphenyl ethers.
  • a selective herbicidal composition that comprises as active component, in addition to inert additives such as carriers, solvents and wetting agents, a mixture comprising
  • X is oxygen or sulfur or, when W is W 5 , may also be NH, NC(O)H or NC(O)R 62 ;
  • Y is -COOH, or an organic or inorganic salt of that acid, II , 11 o o
  • R is -OR H ;
  • Rj is one of the groups (a), (b) and (c)
  • R 2 is hydrogen, methyl or the group Q" (Ql,
  • C is hydrogen, methyl or, together with Q 4 , is -(CH 2 ) 2 -, -( ⁇ 3 -, -CH 2 CH(OH)CH 2 - or -CH 2 SCH 2 -;
  • Q 2 is hydrogen or methyl
  • Q-j is hydrogen, trifluoromethyl, ethynyl, vinyl, phenyl, cyano or C ⁇ alkoxycarbonyl, C j ⁇ alkyl, or C ⁇ alkyl substituted by hydroxy, C alkoxy, mercapto, C j ⁇ al yl- mercapto, vinyl, phenyl, 4-hydroxyphenyl, 4-imidazolyl, 3-indolyl, hydroxy- carbonyl, C ⁇ alkoxycarbonyl, 2-propenyloxycarbonyl, cyano or by carbamoyl; and
  • Q 4 is hydrogen, methyl, hydroxymethyl, formyl or cyano; or R 2 together with R 7 is -(CH 2 ) p -, -CH 2 SCH 2 - or -CH 2 CHOHCH 2 -;
  • R 3 is hydrogen, C ⁇ alkyl, phenyl, or phenyl mono- or di-substituted by fluorine, chlorine, bromine, methyl, trifluoromethyl, methoxy or by nitro;
  • R 4 is hydrogen or methyl
  • R 5 is C ⁇ alkyl, C ⁇ ghaloalkyl, phenyl, benzyl, or phenyl substituted by fluorine, chlorine, bromine, methyl, trifluoromethyl, methoxy, nitro, cyano, carboxy or by C- ⁇ alkoxycarbonyl;
  • R is hydrogen, hydroxymethyl, formyl, cyano, hydroxyimino, C ⁇ alkoxyimino, phosphono, phosphino, methylphosphino or a group COX ⁇
  • R is hydrogen; C ⁇ alkyl or C ⁇ alkyl substituted by hydroxy, C ⁇ alkoxy, mercapto, acylmercapto, C ⁇ alkylthio, vinyl, phenyl, 4-hydroxyphenyl, 4-imidazolyl, 3-indolyl, hydroxycarbonyl, 2-propenyloxycarbonyl, cyano, carbamoyl, methylphosphino or by methylsulfoximino; trifluoromethyl; ethynyl; vinyl or vinyl substituted by chlorine or by methoxy; phenyl or phenyl substituted by fluorine, chlorine, methyl, trifluoromethyl or by methoxy; or cyano or C ⁇ alkoxy- carbonyl; R 8 is hydrogen or methyl; A is oxygen, sulfur or -NH-; m is 1, 2 or 3; n is 0, 1, 2 or 3; p is 2 or 3;
  • X j is hydroxy, C ⁇ alkoxy, C 3 ⁇ alkenyloxy, mercapto, C alkylthio, amino, C ⁇ alkyl- amino, C 2 - 4 dialkylam no or C j ⁇ alkoxyamino; or C-._ 4 al-.0xy, C 3 ⁇ alkenyloxy, mercapto, C alkylthio, amino, C ⁇ al-cylamino, C ⁇ dialkylamino or C ⁇ alkoxy- amino each substituted by phenyl, benzyloxy or by ⁇ alkoxy, or is one of the groups (d), (e) and (f)
  • Aj is oxygen, sulfur or -NH-;
  • R 9 is hydrogen, C- ⁇ alkyl or benzyl
  • R 10 is hydroxymethyl, cyano or a group COQ'
  • Q is hydroxy, C j ⁇ alkoxy, 2-propenyloxy, benzyloxy, amino or the group (d);
  • Q' is hydroxy, C 1 -C 4 alkoxy, 2-propenyloxy, benzyloxy, amino or the group (d);
  • R ⁇ is hydrogen, C 1 -C 10 al yl, C 1 -C 4 alkoxy-C 1 -C 4 alkyl, C 1 -C 4 alkylthio-C 1 -C 4 alkyl, di- C r C 4 alkylamino-C 1 -C 4 alkyl, halo-Ci-Cgal yl, C -C 8 alkenyl, halo-C ⁇ -Cgalkenyl, C 3 -C 8 alkynyl, C 3 -C 7 cycloalkyl, halo-C 3 -C 7 cycloalkyl, C alkylcarbonyl, C 1 -C 4 alkylcarbonyloxy-C 1 -C 2 alkyl, allylcarbonyl, C 3 -C 7 cycloalkylcarbonyl, benzoyl that is unsubstituted or substituted at the phenyl ring by up to three identical or different substituents selected from halogen,
  • W 6 W 6
  • E is nitrogen or -CR 12 ;
  • R 12 is hydrogen, halogen, hydroxy, C 2 -C 4 a.J-.oxy, phenyl or benzyl; or phenyl substituted by C r C 4 alkyl, C r C 4 alkoxy, C j ⁇ haloalkyl or by halogen; benzyl substituted by C r C 4 alkyl, C r C 4 alkoxy, C r C 4 haloalkyl or by halogen; -COR 13 , " ⁇ " R i4 ,
  • R 13 is C r C 4 alkyl, halo-C r C 4 a-kyl, C r C 4 al oxy-C 1 -C 4 alkyl; amino, C r C 4 a---:yla ⁇ -
  • R 18 is hydrogen, methyl or, together with R 17 , is -(CH 2 ) 2 -, -(CH 2 ) 3 -, -(CH 2 ) 4 - or
  • R 19 is hydrogen, methyl, fluorine, chlorine, bromine, Cj-galkoxy, C 3 - 6 alkenyloxy,
  • R 2 ⁇ is C ⁇ alkyl, C 2 . 6 alkenyl, C 3.6 cycloalkyl, C j ⁇ haloalkyl, C 1 - 3 alkoxy, C j .
  • alkylthio formyl, Cx-salkylcarbonyl, carboxy, C ⁇ alkoxycarbonyl, phenyl, or phenyl substit ⁇ uted by fluorine, chlorine, methyl, trifluoromethyl, methoxy or by nitro; or is 2-, 3- ' or 4-pyridyl, 2- or 3-furyl or 2- or 3-thienyl;
  • R 22 is hydrogen, - alkyl, C 3 -C 6 cycloalkyl, C r C 6 haloallcyl, C 3 -C 6 alkenyl,
  • R 57 is hydrogen, hydroxy, C r C,salkoxy, Cx- alkoxyalkoxy, C- t - acyloxyalkoxy, tri- methylsilylethoxy, C C ⁇ alkylsulfonylamino, Cx-Cgalkylthio, imidazolyl, benzyl ⁇ oxy, phenoxy or thiophenoxy, or benzyloxy, phenoxy or thiophenoxy;
  • R 58 is halogen, Cj-C ⁇ haloalkyl, C- j -C ⁇ alkyl, acylamino, C 3 -C 6 cycloalkyl, halo- substituted Ci- alkoxy- carbonyl, C- t -C ⁇ alkoxy, Ci- a ⁇ lamino, di- -Cgalkylamino, C_-C 6 a---:oxyimino- alkyl, acyl, C-t-Cgalkylthio, phen
  • R 66 is Ci-C ⁇ al yl, or C r C 6 alkyl which is substituted by up to 3 fluorine atoms, 1 chlorine atom, 1 C 1 -C 4 alkoxy group, 1 C 1 -C 4 alkoxycarbonyl group, 1 dimethylcarbamoyl group, 1 carbamoyl group, 1 cyano group, 1 vinyl group, 1 ethynyl group or 1 phenyl group which is unsubstituted by fluorine, chlorine, bromine, methyl, trifluoromethyl or methoxy, or is phenyl, or -phenyl which is up to trisubstituted by fluorine, chlorine, bromine, methyl, trifluoromethyl, methoxy or nitro; or NR ⁇ R ⁇ ; or OR ⁇ ;
  • R 67 is hydrogen or C 1 -C 4 alkyl
  • R 68 is hydrogen, -C ⁇ alkyl, phenyl, pyridyl, or phenyl which is monosubstituted to trisubstituted or pyridyl which is monosubstituted by ⁇ alkyl, fluorine, chlorine, bromine, trifluoromethyl, methoxy or nitro; or is -Cgalkylcarbonyl, trifluoro- methylcarbonyl, C 3 -C 6 cycloalkylcarbonyl, benzylcarbonyl, 2-, 3- or 4-pyridyl- carbonyl, 2- or 3-furyl- or thiophenylcarbonyl, benzoyl, or benzoyl which is monosubstituted to disubstituted by fluorine, chlorine, bromine, methyl, tri ⁇ fluoromethyl, methoxy or nitro; or ⁇ al oxycarbonyl, benzoyloxycarbonyl, aminocarbonyl, aminothiocarbonyl,
  • R 69 is hydrogen, C C 6 alkyl or C 2 -C 6 alkenyl, or C 2 -C 6 alkenyl which is substituted by halogen or phenyl, or C 1 -C 4 alkoxycarbonyl-C 1 -C 4 alkyl or C 1 -C alkylthiocarbonyl- C r C 4 al yl;
  • R 24 is hydrogen or C ⁇ a-kyl
  • X 2 is hydrogen or chlorine; or of an N-acylsulfamoylphenylurea of formula lib
  • a 2 is a group
  • R- 25 and R ⁇ independently of one another, are hydrogen, C Cgalkyl, C 3 -C 8 cycloalkyl,
  • R 27 is hydrogen or C 1 -C aU--yl
  • R a is hydrogen, halogen, cyano, trifluoromethyl, nitro, C 1 -C alkyl, C 1 -C alkoxy, C r C 4 alkylthio, C r C 4 alkylsulfmyl, C r C 4 alkylsulfonyl, -COOR j ⁇ -CONR, ⁇ , -COR,,, -SO 2 NR k R m or -OSO 2 -C 1 -C 4 alkyl;
  • R g is hydrogen, halogen, cyano, nitro, C 1 -C 4 al yl, C 1 -C 4 alkylthio,
  • R b and R h independently of one another, are hydrogen, halogen, C r C alkyl, trifluoro ⁇ methyl, C r C 6 alkoxy, C r C 6 allcylthio or -COORJ;
  • R c is hydrogen, halogen, nitro, -Qalkyl or methoxy
  • R d is hydrogen, halogen, nitro, C 1 -C 4 alkyl, C 1 -C alkoxy, C 1 -C 4 alkylthio, C r C 4 alkyl- sulfinyl, C ⁇ alkylsulfonyl, -COOR j or CONR f cR-,,;
  • R e is hydrogen, halogen, C r C 4 alI yl, -COOR j , trifluoromethyl or methoxy; or R d and R-. together form a C 3 -C 4 alkylene bridge;
  • R f is hydrogen, halogen or C 1 -C alkyl
  • R x and R y independently of one another, are hydrogen, halogen, C-t-C ⁇ alkyl, C r C alkoxy, C r C al ylthio, -COOR 28 , trifluoromethyl, nitro or cyano;
  • R j , R k and R m independently of one another, are hydrogen or C 1 -C a ⁇ l; or
  • R k and R ⁇ together form a C 4 -C 6 alkylene bridge that can be interrupted by oxygen, NH or by -N(C r C 4 alkyl)-;
  • R n is C 1 -C 4 al yl, phenyl, or phenyl substituted by halogen, C 1 -C 4 alkyl, methoxy, nitro or by trifluoromethyl;
  • R 28 is hydrogen, -Cioallcyl, C 1 -C 4 alkoxy-C 1 -C 4 alkyl, C 1 -C 4 alkylthio-C 1 -C 4 alkyl, di- C 1 -C 4 alkylamino-C 1 -C alkyl, halo-Cj-Cgalkyl, C 2 -C 8 alkenyl, halo-C ⁇ -Cgalkenyl, C 3 -C 8 alkynyl, C 3 -C 7 cycloalkyl, halo-C 3 -C 7 cycloalkyl, C r C 8 alkylcarbonyl, allyl- carbonyl, C 3 -C 7 cycloal ylcarbonyl, benzoyl that is unsubstituted or substituted at the phenyl ring by up to three identical or different substituents selected from halogen, C r C 4 alkyl, halo-C 1 -C 4 al
  • E 2 is nitrogen or methine
  • R 29 is -CC1 3 , phenyl or halo-substituted phenyl
  • R 30 and R 31 independently of one another, are hydrogen or halogen
  • R 32 is C r C 4 alkyl; or of a chloroacetamide of formula Ed
  • R3 3 and R 34 independendy of one another, are C- Cgalkyl or C ⁇ alkenyl;
  • R 35 and R 36 independently of one another, are hydrogen or C r C 6 alkyl; or R 33 and R34 together are
  • R 37 and R 38 independen ⁇ y of one another, are C 1 -C 4 alkyl; or R 37 and R 38 together are -(CH2)5-;
  • R 39 is hydrogen, C 1 -C alkyl or ⁇
  • R54 an ⁇ 55' independ ⁇ endy of one another, are hydrogen or C 1 -C 4 alkyl; or of an oxime of formula Eh
  • R 63 is hydrogen or chlorine
  • R.54 is cyano or trifluoromethyl; or of a phenylpyrimidine of formula IIi
  • R 65 is hydrogen or methyl.
  • halogen is to be understood as being fluorine, chlorine, bromine and iodine, preferably fluorine, chlorine and bromine.
  • Alkyl is methyl, ethyl, isopropyl, n-propyl, n-butyl, isobutyl, sec-butyl, tert-butyl and die various isomeric pentyl, hexyl, heptyl, octyl, nonyl and decyl radicals.
  • Haloalkyl is, for example, fluoromethyl, difluoromethyl, trifluoromethyl, chloromethyl, dichloromethyl, trichloromethyl, 2,2,2-trifluoroethyl, 2-fluoroethyl, 2-chloroethyl and 2,2,2-trichloroethyl; preferably trichloromethyl, difluorochloromethyl, trifluoromethyl and dichlorofluoromethyl.
  • Alkoxy is, for example, methoxy, ethoxy, propoxy, isopropoxy, n-butoxy, isobutoxy, sec-butoxy and tert-butoxy; preferably methoxy and ethoxy.
  • Haloalkoxy is, for example, fiuoromethoxy, difluoromethoxy, trifluoromethoxy, 2,2,2- trifluoroethoxy, 1,1,2,2-tetra- fluoroethoxy, 2-fluoroethoxy, 2-chloroethoxy and 2,2,2-trichloroethoxy; preferably difluoromemoxy, 2-chloroethoxy and trifluoromethoxy.
  • Alkylthio is, for example, methylthio, ethylthio, propylthio, isopropylthio, n-butylthio, isobutylthio, sec-butylthio, tert-butylthio or isomeric pentylthio, preferably methylthio and ethylthio.
  • Alkenyl is to be understood as being straight-chain or branched alkenyl, such as vinyl, allyl, methallyl, 1-methylvinyl, but-2-en-l-yl, pentenyl, 2-hexenyl or 3-heptenyl. Preference is given to alkenyl radicals having a chain length of 2 or 3 carbon atoms.
  • alkynyl radicals occurring in the definitions of die substituents may be straight-chain or branched, such as, for example, ethynyl, propargyl, 3-butynyl, 1-methylpropargyl, 1-pentynyl or 2-hexynyl. Ethynyl and propargyl are preferred.
  • Cycloalkyl is, for example, cyclopropyl, dimethylcyclopropyl, cyclobutyl, cyclopentyl, methylcyclopentyl, cyclohexyl or cycloheptyl, but preferably cyclopropyl, cyclopentyl or cyclohexyl.
  • Alkoxycarbonyl is, for example: methoxycarbonyl, ethoxycarbonyl, n-propoxycarbonyl, isopropoxycarbonyl and n-butoxycarbonyl, preferably methoxycarbonyl and etiioxy- carbonyl.
  • Alkoxyalkyl is, for example: methoxymethyl, ethoxymethyl, propoxymethyl, methoxy- ethyl, ethoxyethyl, propoxyethyl, methoxypropyl, ethoxypropyl or propoxypropyl.
  • Alkylthioalkyl is, for example: methylthiomethyl, ethylthiomethyl, methylthioethyl, ethyl- thioethyl or isopropylthioethyl.
  • Alkylaminoalkyl is, for example: methylaminoethyl, dimethylaminoethyl, ethylamino- ethyl or diethylaminoethyl.
  • Cyanoalkyl is, for example: cyanomethyl, cyanoethyl or cyanopropyl.
  • Halocycloalkyl is, for example: 2,2-dichlorocyclopropyl or pentachlorocyclohexyl.
  • Alkylsulfonyl is, for example: methylsulfonyl, ethylsulfonyl, propylsulfonyl or butyl- sulfonyl. Methyl- and ed yl-sulfonyl are preferred.
  • Phenyl and thienyl also as part of a substituent such as phenoxy', thiophenoxy, phenylthio, phenoxycarbonyl, phenylaminocarbonyl, benzyl or benzoyl, can generally be unsub ⁇ stituted or substituted by further substituents.
  • the substituents may be in the ortho-, meta- and/or para-position(s) or in 2-, 3-, 4- or 5-position of the thienyl ring, respectively.
  • Preferred substituent positions are the ortho- and para-positions to the ring-linkage point.
  • Preferred substituents are halogen atoms.
  • Suitable salts of the free carboxylic acid are, especially, alkali metal salts such as lithium, sodium, potassium; alkaline earth metal salts such as magnesium or calcium; or salts of manganese, copper, zinc or iron; or salts of organic ammonium bases, such as ammonia, primary, secondary or tertiary alkylamines, such as methylammonium, dietiiylammonium, methylammonium, morpholinium, tetrabutylammonium, benzyltrimethylammonium, phosphonium, sulfonium, sulfoxonium or pyridinium.
  • alkali metal salts such as lithium, sodium, potassium
  • alkaline earth metal salts such as magnesium or calcium
  • salts of manganese, copper, zinc or iron or salts of organic ammonium bases, such as ammonia, primary, secondary or tertiary alkylamines, such as methylammonium, dietiiylammonium, methyl
  • the invention relates also to salts that the compounds of formula I are capable of forming with amines, alkali and alkaline earth metal bases or quaternary ammonium bases.
  • those salts also include hydrazonium salts that may be formed by compounds of formula I wherein R 2 is the group Q". Salt formation can also be effected by die addition of a strong acid to die pyrimidine moiety of d e compounds of formula I. Suitable acids for that purpose are hydrochloric acid, hydrobromic acid, sulfuric acid or nitric acid.
  • Alkali metal and alkaline earth metal hydroxides that are especially suitable as salt formers are the hydroxides of lidiium, sodium, potassium, magnesium or calcium, but especially those of sodium or potassium.
  • amines suitable for die formation of ammonium cations are botii ammonia and primary, secondary and tertiary C r C 4 alkylamines, C 1 -C 4 -hydroxyalkylamines and C 2 -C 4 alkoxyalkylamines, for example methylamine, ethylamine, n-propylamine, isopropylamine, the four isomeric butylamines, n-amylamine, isoamylamine, hexylamine, heptylamine, octylamine, nonylamine, decylamine, pentadecylamine, hexadecylamine, heptadecylamine, octadecylamine, methyl-ethylamine, methyl-isopropylamine, methyl- hexylamine, methyl-nonylamine, methyl-pentadecylamine, methyl-o
  • Examples of quaternary ammonium bases are generally the cations of ammonium halides, for example the tetramethylammonium cation, d e trimethylb ⁇ nzylammonium cation, the triethylbenzylammonium cation, die tetraethylammonium cation, the trimethylethyl- ammonium cation, and also the ammonium cation.
  • Y is preferably -COOH, or an organic or inorganic salt of that acid, o
  • tiiat group special preference is given to those compounds wherein R 12 is hydrogen, halogen, -OCH 3 or -COR 13 , wherein R 13 is especially ⁇ alkyl. Preference is also given to tiiose compounds wherein W is W ! and
  • compositions according to the invention are used, a herbicid ⁇ ally active pyrimidine of formula I, the above-mentioned preferences being given special mention, and as safener a herbicide-antagonistically effective amount of a quinoline derivative of formula Eg
  • tiiose compositions according to die invention tiiat comprise a herbicide of formula I, special mention being made of the above-mentioned prefe ⁇ ed substituents, and a herbicide-antagonistically effective amount of a safener of formula lib wherein R 25 is C-i-C ⁇ alkyl, especially methyl, R 2 g is hydrogen or C 1 -C alkyl, R 27 is
  • a 2 is a group , wherein R ⁇ is
  • R g is hydrogen, mediyl or methoxy, ⁇ is methyl or methoxy, and R ⁇ R ⁇ and R f are hydrogen.
  • compositions according to die invention comprise a herbicide of formula I, special mention being made of die above-mentioned preferred substituents, and a herbicide-antagonistically effective amount of a safener of formula He wherein R 29 is preferably phenyl or halo-substituted phenyl, R 30 is 2-Cl, R 32 is ⁇ methyl and E is methine.
  • compositions according to die invention comprise a herbicide of formula I, me above-mentioned preferred substituents being given special mention, and a herbicide-antagonistically effective amount of a safener of formula Ed wherein R 33 and
  • R ⁇ are allyl, or R 33 and R ⁇ together are ; or R 33 and R 34 together are
  • R37. 3 8 an d R39 ai -- eac ⁇ methyl; or R 39 is hydrogen; or R 37 and R 3 g together are
  • R, ⁇ , R 50 , R5 1 and R 52 are preferably hydrogen.
  • compositions according to die invention comprise as herbicide a compound of formula If
  • Y is -COOCH 3 and R 12 is hydrogen; or b) Y is -COOCH 3 and R 12 is methylcarbonyl; or c) Y is -COOCH 3 and R 12 is ethylcarbonyl; or d) Y is -COOH and R 12 is hydrogen; or e) Y is -COOH and R 12 is fluorine; or f) Y is -COOH and R 12 is methoxy; or g) Y is 2-chlorophenylhydrazinoyl and R 1 is methoxy; or h) Y is 2-fluorophenylhydrazinoyl and R 12 is methoxy; or i) Y is o-tolylhydrazinoyl and R 12 is methoxy; or j) Y is -NHNHC(CH 3 ) 3 and R 12 is hydrogen; or k) Y is 2-phenylhydrazinoyl and R 12 is hydrogen; or
  • Y is 2-fluorophenylhydrazinoyl and R 12 is hydrogen; m) Y is 2-trifluoromethylphenylhydrazinoyl and R 12 is hydrogen; or n) Y is o-tolylhydrazinoyl and R 12 is hydrogen; or o) Y is 4-chlorophenylhydrazinoyl and R 12 is hydrogen;
  • Y is -NH- CH- C - NH 2 and R 12 is hydrogen; or C 2 H 5
  • a 2 is die group and R 26 is hydrogen; or of a compound of formula Ee
  • a 2 is die group H and R 26 is hydrogen; or of a compound of formula Ee
  • a 2 is the group and R 26 is med yl
  • a 2 is die group and R 26 is mediyl.
  • tiiat group of compositions according to d e invention special preference is made of tiiose that comprise as herbicide a compound of formula If wherein
  • Y is -COOCH 3 and R 12 is hydrogen; or b) Y is -COOCH 3 and R 12 is ethylcarbonyl; or c) Y is -COOH and R 12 is hydrogen; or
  • a 2 is die group and R 26 is hydrogen; or of a compound of formula Ee
  • a 2 is the group and R 26 is hydrogen
  • a 2 is the group and R 26 is methyl
  • a 2 is the group and R 6 is mediyl.
  • herbicides of formula I can advantageously also be combined wid the safeners mentioned in the following Tables 9 and 10 to form compositions according to the invention:
  • compositions according to die invention comprise die following herbicide/safener combinations:
  • the invention relates also to a method for the selective control of weeds in crops of useful plants, which meti od comprises treating die useful plants, the seeds or seedlings thereof or the cultivated area diereof with a herbicidally effective amount of the pyrimidine of formula I and a herbicide-antagonistically effective amount of a safener of formula Ha, lib, He, ⁇ d, Eh or IIi, simultaneously or independendy of one another.
  • Crop plants that can be protected against die damaging effect of the above-mentioned herbicides by die safeners of formula Ea, lib, Ec, Ed, Eh or Hi are especially those tiiat are important in the food and textile sectors, for example sugar cane and, especially, sorghum, maize, rice and other species of cereal (wheat, rye, barley, oats), most especially wheat and maize.
  • the weeds to be controlled may be bom monocotyledonous and dicotyledonous weeds.
  • Cultivated areas will be understood as meaning areas of land in which the crop plants are already growing or in which the seed of tiiose crop plants has already been sown, and also ground intended for growing those crop plants.
  • a safener or antidote of formula Ha, Eb, He, Ed, Hh or Hi can, depending on die intended use, be used to pre-treat the seed of die crop plant (dressing die seeds or seedlings) or can be introduced into die soil before or after sowing has taken place. It can, however, also be applied by itself or together witii the herbicide before or after the emergence of die plants.
  • the treatment of the plant or the seed witii die safener can therefore in principle take place independendy of die time of application of die phytotoxic chemical.
  • the plant can, however, also be treated by applying die phytotoxic chemical and the safener simultan ⁇ eously (tank mixture).
  • Preemergence treatment includes botii treatment of the cultivated area before sowing and treatment of cultivated areas in which seed has been sown but in which die plants have not yet grown.
  • the rate of application of die safener relative to tiiat of die herbicide depends largely on die mode of application.
  • die mode of application which is effected either using a tank mixture with a combination of safener and herbicide or by separate application of safener and herbicide
  • d e ratio of safener to herbicide is generally from 1:100 to 10:1, preferably from 1:20 to 1:1, and especially 1:1.
  • much lower amounts of safener are required relative to die rate of application of herbicide per hectare of cultivated area.
  • the rate of application of herbicide is generally from 0.001 to 2 kg/ha, but preferably from 0.05 to 1 kg/ha.
  • safener/kg of seed In the case of seed-dressing, 0.001 to 10 g of safener/kg of seed, preferably 0.05 to 2 g of safener/kg of seed, will generally be applied. If die safener is applied in liquid form by seed soaking shortly before sowing, then it is advantageous to use safener solutions that comprise the active ingredient in a concentration of 1 to 10000 ppm, preferably 100 to 1000 ppm.
  • the compounds of formula H or combinations of compounds of formula Ea, Eb, Ec, Hd, Eh or Ei witii the herbicides of formula I to be antagonised are advantageously used togetiier with die adjuvants conventionally employed in formulation technology, and are dierefore formulated in known manner, e.g. into emulsifiable concentrates, coatable pastes, directly sprayable or dilutable solutions, dilute emulsions, wettable powders, soluble powders, dusts, granules, and also encapsulations in e.g. polymer substances.
  • die methods of application such as spraying, atomising, dusting, scattering, coating or pouring, are chosen in accordance witii die intended objectives and the prevailing circumstances.
  • compositions, preparations or mixtures comprising the compound (active ingredient) of formula E, or a combination of the compound of formula Ha, Eb, Ec, Hd, Eh or Ei with die herbicide of formula I to be antagonised, and, where appropriate, a solid or liquid adjuvant, are prepared in known manner, e.g. by homogeneously mixing and/or grinding d e active ingredients witii extenders, e.g. solvents, solid carriers and, where appropriate, surface-active compounds (surfactants).
  • Suitable solvents are: aromatic hydrocarbons, preferably die fractions containing 8 to 12 carbon atoms, e.g. xylene mixtures or substituted naphthalenes, phthalates such as dibutyl phthalate or dioctyl phthalate, aliphatic hydrocarbons such as cyclohexane or paraffins, alcohols and glycols and tiieir ethers and esters, such as ethanol, ethylene glycol, ethylene glycol monomediyl or monoethyl etiier, ketones such as cyclohexanone, strongly polar solvents such as N-methyl-2-pyrrolidone, dimethyl sulfoxide or dimethylformamide, as well as vegetable oils or epoxidised vegetable oils, such as epoxidised coconut oil or soybean oil; or water.
  • aromatic hydrocarbons preferably die fractions containing 8 to 12 carbon atoms, e.g. xylene mixtures or substituted na
  • the solid carriers used e.g. for dusts and dispersible powders are normally natural mineral fillers such as calcite, talcum, kaolin, montmoriUonite or attapulgite.
  • Suitable granulated adsorptive carriers are porous types, for example pumice, broken brick, sepiolite or bentonite; and suitable nonsorbent carriers are, for example, calcite or sand.
  • a great number of pregranulated materials of inorganic or organic nature can be used, e.g. especially dolomite or pulverised plant residues.
  • suitable surface-active compounds are nonionic, cationic and/or anionic surfactants having good emulsifying, dispersing and wetting properties.
  • surfactants will also be understood as comprising mixtures of surfactants.
  • Botii so-called water-soluble soaps and water-soluble syndietic surface-active compounds are suitable anionic surfactants.
  • Suitable soaps are the alkali metal salts, alkaline earth metal salts or unsubstituted or substituted ammonium salts of higher fatty acids (C 10 -C 22 ), e.g. the sodium or potassium salts of oleic or stearic acid or of natural fatty acid mixtures which can be obtained e.g. from coconut oil or tallow oil. Fatty acid mediyltaurin salts may also be mentioned.
  • syndietic surfactants especially fatty sulfonates, fatty sulfates, sulfonated benzunidazole derivatives or alkylarylsulfonates.
  • the fatty sulfonates or sulfates are usually in the form of alkali metal salts, alkaline earth metal salts or unsubstituted or substituted ammonium salts and contain a C 8 -C 22 alkyl radical which also includes die alkyl moiety of acyl radicals, e.g. the sodium or calcium salt of lignosulfonic acid, of dodecylsulfate or of a mixture of fatty alcohol sulfates obtained from natural fatty acids. These compounds also comprise die salts of sulfated and sulfonated fatty alcohol/ethylene oxide adducts.
  • the sulfonated benzimidazole derivatives preferably contain 2 sulfonic acid groups and one fatty acid radical containing 8 to 22 carbon atoms.
  • alkylarylsulfonates are the sodium, calcium or triethanolamine salts of dodecylbenzenesulfonic acid, dibutylnaphthalenesulfonic acid, or of a condensate of naphthalenesulfonic acid and formaldehyde.
  • corresponding phosphates e.g. salts of die phosphoric acid ester of an adduct of p-nonylphenol with 4 to 14 moles of ediylene oxide, or phospholipids.
  • Non-ionic surfactants are preferably polyglycol ether derivatives of aliphatic or cyclo- aliphatic alcohols, saturated or unsaturated fatty acids and alkylphenols, said derivatives containing 3 to 30 glycol ether groups and 8 to 20 carbon atoms in the (aliphatic) hydro ⁇ carbon moiety and 6 to 18 carbon atoms in the alkyl moiety of the alkylphenols.
  • non-ionic surfactants are the water-soluble adducts of polyethylene oxide widi polypropylene glycol, ethylenediaminopolypropylene glycol and alkylpolypropylene glycol containing 1 to 10 carbon atoms in the alkyl chain, which adducts contain 20 to 250 ethylene glycol etiier groups and 10 to 100 propylene glycol ether groups. These compounds usually contain 1 to 5 ethylene glycol units per propylene glycol unit.
  • non-ionic surfactants are nonylphenolpoly ethoxy edianols, castor oil polyglycol ethers, polypropylene/polyethylene ojtide adducts, tributylphenoxy- polyethoxyethanol, polyethylene glycol and octylphenoxy-polyethoxyetiianol.
  • Fatty acid esters of polyoxyethylene sorbitan e.g. polyoxyethylene sorbitan trioleate, are also suitable.
  • Cationic surfactants are preferably quaternary ammonium salts which contain, as N-substituent, at least one C 8 -C 2 alkyl radical and, as further substituents, unsubstituted or halogenated lower alkyl, benzyl or hydroxy-lower alkyl radicals.
  • the salts are preferably in die form of halides, mediyl sulfates or ethyl sulfates, e.g. stearyltrimethyl-ammonium chloride or benzyldi(2-chloroethyl)ethylammonium bromide.
  • the agrochemical compositions usually comprise 0.1 to 99 % by weight, preferably 0.1 to 95 % by weight, of a compound of formula Ea, Eb, He, Ed, Eh or Ei or a mixture of antidote and herbicide, 1 to 99.9 % by weight, preferably 5 to 99.8 % by weight, of a solid or liquid adjuvant and 0 to 25 % by weight, preferably 0.1 to 25 % by weight, of a surfactant.
  • compositions may also comprise further ingredients such as stabilisers, antifoams, viscosity regulators, binders and tackifiers, as well as fertilisers or other active ingredients for obtaining special effects.
  • Seed dressing a) Dressing the seeds with a wettable powder formulation of a compound of formula Ea, lib, He, Ed, Eh or Hi by shaking in a vessel until the formulation is evenly distributed over the surface of die seeds (dry dressing). Approximately 1 to 500 g of a compound of formula Ha, Hb, Ec, Ed, Eh or Ei (4 g to 2 kg of wettable powder) are used per 100 kg of seed.
  • Dressing d e seed or treating die germinated seedling are naturally the preferred mediods of application since the active ingredient treatment is directed wholly at the target crop.
  • a liquid formulation of a mixture of antidote and herbicide (ratio of the one to the other from 10:1 to 1:100) is used, die rate of application of herbicide being 0.01 to 5.0 kg per hectare.
  • a tank mixture of this type is applied before or after sowing.
  • the antidote is introduced in d e form of an emulsifiable concentrate, wettable powder or granules into the open, sown seed furrow and tiien, after covering the seed furrow, die herbicide is applied preemergence in die normal manner.
  • a solution of a compound of formula Ea, Hb, Ec, Ed, Hh or Hi is applied to mineral granule carriers or polymerised granules (urea/formaldehyde) and allowed to dry. If desired, a coating may be applied (coated granules) that allows the active ingredient to be released in metered amounts over a specific period of time.
  • Emulsifiable concentrates compound mixture calcium dodecylbenzenesulfonate castor oil polyethylene glycol etiier (36 moles of ethylene ojride) tributylphenol polyethylene glycol ether (30 moles of ethylene oxide) cyclohexanone xylene mixture 65 %
  • Emulsions of any desired concentration can be produced from such concentrates by dilution witii water.
  • the active ingredient is dissolved in methylene chloride, die solution is sprayed onto die carrier, and die solvent is subsequendy evaporated off in vacuo.
  • Dusts compound mixture highly dispersed silicic acid talcum kaolin - 90 %
  • Wettable powders compound mixture sodium lignosulfonate sodium laurylsulfate sodium diisobutylnaphdialene- sulfonate - 6 % 10 % octylphenol polyethylene glycol ether (7-8 moles of ediylene oxide) - 2 % highly dispersed silicic acid 5 % 10 % 10 % kaolin 62 % 27 %
  • the active ingredient is thoroughly mixed widi the adjuvants and die mixture is thoroughly ground in a suitable mill, affording wettable powders which can be diluted with water to give suspensions of the desired concentration.
  • Emulsifiable concentrates compound mixture 10 % octylphenol polyethylene glycol etiier (4-5 moles of ethylene oxide) 3 % calcium dodecylbenzenesulfonate 3 % castor oil polyglycol ether
  • Emulsions of any required concentration can be obtained from tiiis concentrate by dilution witii water.
  • Ready-for-use dusts arc obtained by mixing the active ingredient witii the carriers and grinding die mixture in a suitable mill.
  • Extruder granules compound mixture 10 % sodium lignosulfonate 2 % carboxymethylcellulose 1 % kaolin 87 %
  • the active ingredient is mixed and ground witii the adjuvants, and die mixture is subsequently moistened witii water.
  • the mixture is extruded and tiien dried in a stream of air.
  • the finely ground active ingredient is uniformly applied, in a mixer, to the kaolin moistened witii polyethylene glycol.
  • Non-dusty coated granules are obtained in tiiis manner.
  • the finely ground active ingredient is intimately mixed with die adjuvants, giving a suspension concentrate from which suspensions of any desired concentration can be obtained by dilution witii water.
  • Example B3 Safener action on maize and wheat:
  • Example B5 Safener action on wheat, barley and rice:
  • Example B6 Safener action on maize and wheat:
  • Example B7 Safener action on maize and wheat:

Landscapes

  • 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

Composition herbicide sélective destinée à la lutte contre les mauvaises herbes dans les cultures de plantes utiles. Elle comporte (a) une quantité à efficacité herbicide d'une pyrimidine répondant à la formule (I), dans laquelle les substituants ont les notations précisées dans la revendication no. 1; et (b), à titre d'antidote de protection des cultures utiles, une quantité à efficacité antagoniste pour l'herbicide, d'un dérivé de quinoléine répondant à la formule (IIa), dans laquelle R24 représente hydrogène ou alkyle C1-8 et X2 représente hydrogène ou chlore; ou d'une N-acylsulfamoylphénylurée répondant à la formule (IIb), dans laquelle les substituants ont les notations précisées dans la revendication no. 1; ou d'un dérivé d'acide 1-phénylazole-3-carboxylique répondant à la formule (IIc), dans laquelle les substituants ont les notations précisées dans la revendication no. 1, ou d'un chloroacétamide répondant à la formule (IId), dans laquelle les substituants ont les notations précisées dans la revendication no. 1; ou d'une oxime répondant à la formule (IIh), dans laquelle les substituants ont les notations précisées dans la revendication no.1; ou d'une phénylpyrimidine répondant à la formule (IIi), dans laquelle les substituants ont les notations précisées dans la revendication no. 1.
EP93915750A 1992-07-08 1993-06-30 Composition herbicide selective Withdrawn EP0671880A1 (fr)

Applications Claiming Priority (7)

Application Number Priority Date Filing Date Title
CH2148/92 1992-07-08
CH214892 1992-07-08
CH3007/92 1992-09-25
CH300792 1992-09-25
CH42393 1993-02-11
CH423/93 1993-02-11
PCT/EP1993/001683 WO1994000987A2 (fr) 1992-07-08 1993-06-30 Composition herbicide selective

Publications (1)

Publication Number Publication Date
EP0671880A1 true EP0671880A1 (fr) 1995-09-20

Family

ID=27172092

Family Applications (1)

Application Number Title Priority Date Filing Date
EP93915750A Withdrawn EP0671880A1 (fr) 1992-07-08 1993-06-30 Composition herbicide selective

Country Status (5)

Country Link
EP (1) EP0671880A1 (fr)
AU (1) AU4562093A (fr)
IL (1) IL106281A0 (fr)
MX (1) MX9304102A (fr)
WO (1) WO1994000987A2 (fr)

Cited By (1)

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CN102093286B (zh) * 2009-12-10 2013-01-09 天津药物研究院 丙烯酸类内皮素受体拮抗剂及其制备方法和用途

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DE4310220A1 (de) * 1993-03-30 1994-10-06 Basf Ag Herbizide Mittel, enthaltend einen oder mehrere herbizide Wirkstoffe aus der Gruppe der Salizylsäurederivate und ein oder mehrere antidotisierend wirkende Verbindungen
DE19533023B4 (de) 1994-10-14 2007-05-16 Basf Ag Neue Carbonsäurederivate, ihre Herstellung und Verwendung
CA2209902A1 (fr) * 1995-01-19 1996-07-25 Novartis Ag Composition herbicide
WO1996029870A1 (fr) * 1995-03-30 1996-10-03 Ciba-Geigy Ag Compositions herbicides
EA001418B1 (ru) * 1995-11-23 2001-02-26 Новартис Аг Гербицидная композиция
US7071146B1 (en) 1996-11-11 2006-07-04 Syngenta Crop Protection, Inc. Herbicidal composition
WO1998031226A1 (fr) * 1997-01-15 1998-07-23 Novartis Ag Agent herbicide
US6376424B1 (en) 1998-01-21 2002-04-23 Syngenta Crop Protection, Inc. Herbicidal composition
MXPA03003747A (es) * 2000-11-01 2003-07-28 Syngenta Participations Ag Composicion agroquimica.
AR048441A1 (es) 2004-03-26 2006-04-26 Syngenta Participations Ag Una combinacion herbicida

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AU587539B2 (en) * 1986-06-14 1989-08-17 Ihara Chemical Industry Co. Ltd. Picolinic acid derivatives and herbicidal compositions
US5256630A (en) * 1987-08-13 1993-10-26 Monsanto Company Safening mixtures of sulfonylurea and acetanilide herbicides
JPH02262565A (ja) * 1988-12-19 1990-10-25 Mitsui Toatsu Chem Inc ピリミジン誘導体、その製造法およびこれらを含有する除草剤ならびに除草剤組成物
PH27460A (en) * 1989-12-28 1993-07-09 Kumiai Chemical Industry Co Pyrimidine derivatives and herbicidal composition containing the same
ATE234559T1 (de) * 1990-12-21 2003-04-15 Bayer Cropscience Gmbh Mischungen aus herbiziden und antidots
ES2071507T3 (es) * 1991-06-29 1995-06-16 Hoechst Schering Agrevo Gmbh Nuevas mezclas de herbicidas y antidotos.

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102093286B (zh) * 2009-12-10 2013-01-09 天津药物研究院 丙烯酸类内皮素受体拮抗剂及其制备方法和用途

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WO1994000987A2 (fr) 1994-01-20
MX9304102A (es) 1994-01-31
AU4562093A (en) 1994-01-31
WO1994000987A3 (fr) 1994-03-17
IL106281A0 (en) 1993-11-15

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