EP0629192A1 - Composes de pyrimidinyle et de triazinyle a activite herbicide - Google Patents

Composes de pyrimidinyle et de triazinyle a activite herbicide

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Publication number
EP0629192A1
EP0629192A1 EP92923193A EP92923193A EP0629192A1 EP 0629192 A1 EP0629192 A1 EP 0629192A1 EP 92923193 A EP92923193 A EP 92923193A EP 92923193 A EP92923193 A EP 92923193A EP 0629192 A1 EP0629192 A1 EP 0629192A1
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EP
European Patent Office
Prior art keywords
methyl
alkoxy
alkyl
hydrogen
formula
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.)
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Application number
EP92923193A
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German (de)
English (en)
Inventor
Christoph Lüthy
Paul Winternitz
William Rudolf Lutz
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Novartis AG
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Ciba Geigy AG
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Publication date
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Publication of EP0629192A1 publication Critical patent/EP0629192A1/fr
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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • 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
    • 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
    • A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
    • A01N43/66—1,3,5-Triazines, not hydrogenated and not substituted at the ring nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
    • C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
    • C07D239/52—Two oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
    • C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
    • C07D239/60—Three or more oxygen or sulfur atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
    • C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
    • C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D251/26—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hetero atoms directly attached to ring carbon atoms
    • C07D251/30—Only oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D419/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen, oxygen, and sulfur atoms as the only ring hetero atoms
    • C07D419/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen, oxygen, and sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D419/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen, oxygen, and sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links

Definitions

  • the present invention relates to novel, herbicidally active pyrimidinyl and triazinyl ethers and thioethers, to processes for their preparation, to compositions comprising them as active ingredients, and to their use for controlling weeds, especially selectively in crops of useful plants.
  • Pyrimidinyl and triazinyl ethers and thioethers having herbicidal action are generally known. Such compounds are described, for example, in European Patent Applications Nos.0400741 and 0409 369. The compounds disclosed therein are not always capable, however, of fulfilling requirements in terms of strength of action and selectivity. Novel herbicidally active pyrimidinyl and triazinyl ethers and thioethers have now been found.
  • X is oxygen or CHR 26 ;
  • Y is oxygen or sulfur
  • A is hydrogen, fluorine, chlorine, (C 1-3 alkyl-oxetan-S-yl)oxy, R 8 or the group
  • E is methine, halo-substituted methine or nitrogen;
  • E 1 is methine or nitrogen
  • Y 1 is oxygen or sulfur
  • each of R 1 and R 24 is C 1-3 alkyl, cyclopropyl, C 1-3 alkoxy, difluoromethoxy, methylthio, ethylthio, methylamino, ethylamino, dimethylamino or diethylamino;
  • each of R 2 and R 25 independendy of the other, is methyl, methoxy, ethoxy or difluoromethoxy;
  • R 3 is hydrogen, C 1-4 alkyl, C 1-3 alkylthio, halogen, C 1-3 alkoxy, C 1-3 alkylamino or
  • C 1-2 dialkylamino or, together with R 4 , is -(CH 2 ) p - or -S(CH 2 ) q S-;
  • R 4 is C 1-6 alkyl, C 2-6 alkenyl, C 3-6 cycloalkyl, C 1-6 haloalkyl, C 1-3 alkylthio, formyl,
  • R 5 is hydrogen, C 1-4 alkyl, halogen, C 1-3 alkoxy or, together with R 6 , is -(CH 2 ) p -;
  • R 6 is hydrogen or C 1-5 alkyl
  • R 7 is hydrogen, hydroxy, halogen, C 1-6 alkoxy, carboxy or C 1-4 alkoxycarbonyl
  • R 8 is hydroxy, C 1-6 alkoxy, C 1-2 alkoxy-C 1-2 alkoxy, C 1-2 alkylthio-C 1-2 alkoxy, C 1-2 alkylsulfinyl-C 1-2 alkoxy, C 2-4 dialkylamino-C 1-2 alkoxy, C 1-3 alkoxycarbonyl-C 1-2 alkoxy,
  • R 9 is hydrogen, methyl or, together with R 10 , is -(CH 2 ) q -, -CH 2 CH(OH)CH 2 - or
  • each of R 10 and R 22 is hydrogen, methyl, hydroxymethyl, formyl, cyano or a group COZ,
  • R 11 is hydrogen, C 1-4 alkyl, or C 1-4 alkyl substituted by hydroxy, C 1-4 alkoxy, mercapto, C 1-4 alkylmercapto, vinyl, phenyl, 4-hydroxyphenyl, 4-imidazolyl, 3-indolyl, hydroxycarbonyl, C 1-4 alkoxycarbonyl, 2-propenyloxycarbonyl, cyano or by carbamoyl, or is trifluoromethyl, ethynyl, vinyl, phenyl, cyano or C 1-4 alkoxycarbonyl;
  • R 12 , R 19 , R 23 and R 27 are hydrogen or methyl
  • R 13 is hydrogen, C 1-4 alkyl, phenyl, or phenyl mono- or di-substituted by fluorine, chlorine, bromine, methyl, trifluoromethyl, methoxy or by nitro;
  • R 14 is hydrogen or methyl
  • R 15 is C 1-6 alkyl, C 1-6 haloalkyl, phenyl, benzyl, or phenyl substituted by fluorine, chlorine, bromine, methyl, trifluoromethyl, methoxy, nitro, cyano, carboxy or by C 1-3 alkoxycarbonyl;
  • n 1, 2 or 3;
  • q 2 or 3
  • W is oxygen, sulfur or NH
  • Z is hydroxy, C 1-4 alkoxy, C 3-4 alkenyloxy, benzyloxy, amino, C 1-4 alkylamino, C 2-4 dialkylammo, or a group
  • each of R 16 and R 18 is hydroxy, C 1-4 alkoxy, 2-propenyloxy, benzyloxy, amino or a group
  • each of R 17 and R 28 independently of the other, is hydrogen, C 1-4 alkyl or benzyl;
  • R 20 is C 1-6 alkyl, C 2-6 alkenyl, C 3-6 cycloalkyl, C 1-6 haloalkyl, C 1-3 alkoxy, C 1-3 alkylthio, carboxy, C 1-4 alkoxycarbonyl, phenyl, or phenyl substituted by fluorine, chlorine, methyl, trifluoromethyl, methoxy or by nitro, or is 2-, 3- or 4-pyridyl, 2- or 3-furyl or 2- or
  • R 21 is hydrogen, C 1-4 alkyl, C 1-3 alkylthio or, together with R 20 , is -(CH 2 ) p - or -S(CH 2 ) q S-;
  • R- 26 is hydrogen or C 1-4 alkyl
  • R 29 is hydroxy, C 1-4 alkoxy, 2-propenyloxy, benzyloxy, or amino;
  • R 3 is C 1-4 alkyl, C 1-3 alkylthio or, together with R 4 , is -(CH 2 ) p - or -S(CH 2 ) q S- when at the same time
  • A is a group R 8 or a group
  • a 4 and R 4 is C 1-6 alkyl, C 2-6 alkenyl, C 3-6 cycloalkyl,
  • the compounds of formula I may occur in the form of optical isomers.
  • Formula I thus includes all possible stereoisomers in the form of enantiomers, tautomers, diastereoisomers, E/Z isomers, or mixtures thereof.
  • alkyl, alkenyl and alkynyl radicals may be straight-chain or branched. The same is true of the alkyl moiety or each alkyl moiety of alkoxy, alkylthio, alkoxycarbonyl (and accordingly C 1-4 carboxy) groups and other alkyl-containing groups.
  • C 1-6 alkyl is, for example, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, pentyl and isomeric pentyl and also hexyl and isomeric hexyl.
  • the C 2-4 alkenyl and C 2-4 alkynyl radicals occurring in the substituents may likewise be straight-chain or branched, such as vinyl, allyl, methallyl, 1-methylvinyl, but-2-en-1-yl, 2-propyn-1-yl, 1-methyl-2-propyn-1-yl and 2-butyn-1-yl.
  • Halomethyl is, for example, chloromethyl, fluoromethyl or trifluoromethyl.
  • C 1-3 alkyl-oxetan-3-yl)oxy is to be understood as being, for example, (oxetan-3-yl)oxy, (3-methyl-oxetan-3-yl)oxy, (3-ethyl-oxetan-3-yl)oxy and (4-methyloxetan-3-yl)oxy.
  • Alkoxycarbonyl is, for example: methoxycarbonyl, ethoxycarbonyl, n-propoxycarbonyl, isopropoxycarbonyl and n-butoxycarbonyl, tert-butoxycarbonyl, preferably methoxycarbonyl and ethoxycarbonyl.
  • Suitable salts of the free carboxy groups are especially alkali metal salts such as lithium, sodium, potassium, alkaline earth metal salts such as magnesium, calcium or salts of organic ammonium bases, such as ammonia, primary, secondary or tertiary alkylamines, such as methylammonium, diethylammonium, triethylammonium, morpholinium or pyridinium.
  • alkali metal salts such as lithium, sodium, potassium, alkaline earth metal salts such as magnesium, calcium or salts of organic ammonium bases, such as ammonia, primary, secondary or tertiary alkylamines, such as methylammonium, diethylammonium, triethylammonium, morpholinium or pyridinium.
  • Y is oxygen or sulfur
  • A is hydrogen, fluorine, chlorine, (C 1-3 alkyl-oxetan-3-yl)oxy, R 8 or the group
  • E is methine or nitrogen
  • E 1 is methine or nitrogen
  • Y 1 is oxygen or sulfur
  • each of R 1 and R 24 is C 1-3 alkyl, cyclopropyl, C 1-4 alkoxy, difluoromethoxy, methylthio, ethylthio, methylamino, ethylamino, dimethylamino or diethylamino;
  • each of R 2 and R 25 is methyl, methoxy, ethoxy or difluoromethoxy;
  • R 3 is hydrogen, C 1-4 alkyl, C 1-3 alkylthio or, together with R 4 , is -(CH 2 ) p - or -S(CH 2 ) q S-;
  • R 4 is C 1-6 alkyl, C 2-6 alkenyl, C 3-6 cycloalkyl, C 1-6 haloalkyl, C 1-3 alkylthio, formyl,
  • R 5 is hydrogen, C 1-4 alkyl or, together with R 5 , is -(CH 2 ) p -;
  • R 6 is hydrogen or C 1-5 alkyl
  • R 7 is hydrogen, hydroxy, C 1-6 alkoxy, carboxy or C 1-4 alkoxycarbonyl
  • R 8 is hydroxy, C 1-6 alkoxy, C 1-2 alkoxy-C 1-2 alkoxy, C 1-2 alkylthio- C 1-2 alkoxy, C 1-2 alkylsulfinyl-C 1-2 alkoxy, C 2-4 dialkylamino-C 1-2 alkoxy, C 1-3 alkoxycarbonyl-C 1-2 alkoxy, C 3-4 alkenyloxy, C 3-4 alkynyloxy, C 3-6 cycloalkoxy, benzyloxy, C 2-4 alkylaminooxy,
  • R 9 is hydrogen, methyl or, together with R 10 , is -(CH 2 ) q -, -CH 2 CH(OH)CH 2 - or
  • each of R 10 and R 22 is hydrogen, methyl, hydroxymethyl, formyl, cyano or a group COZ,
  • R 11 is hydrogen, C 1-4 alkyl, or C 1-4 alkyl substituted by hydroxy, C 1-4 alkoxy, mercapto, C 1-4 alkylmercapto, vinyl, phenyl, 4-hydroxyphenyl, 4-imidazolyl, 3-indolyl, hydroxycarbonyl, C 1-4 alkoxycarbonyl, 2-propenyloxycarbonyl, cyano or by carbamoyl, or is trifluoromethyl, ethynyl, vinyl, phenyl, cyano or C 1-4 alkoxycarbonyl;
  • R 12 , R 19 and R 23 are hydrogen or methyl
  • R 13 is hydrogen, C 1-4 alkyl, phenyl, or phenyl mono- or di-substituted by fluorine, chlorine, bromine, methyl, trifluoromethyl, methoxy or by nitro;
  • R 14 is hydrogen or methyl
  • R 15 is C 1-6 alkyl, C 1-6 haloalkyl, phenyl, benzyl, or phenyl substituted by fluorine, chlorine, bromine, methyl, trifluoromethyl, methoxy, nitro, cyano, carboxy or by C 1-3 alkoxycarbonyl;
  • n 1, 2 or 3;
  • n 0, 1, 2 or 3;
  • p 4 or 5;
  • q 2 or 3
  • W is oxygen, sulfur or NH
  • Z is hydroxy, C 1-4 alkoxy, C 3-4 alkenyloxy, benzyloxy, amino, C 1-4 alkylamino, C 2-4 dialkylamino, or a group or
  • each of R 16 and R 18 is hydroxy, C 1-4 alkoxy, 2-propenyloxy, benzyloxy or amino;
  • R 17 is hydrogen, C 1-4 alkyl or benzyl
  • R 20 is C 1-6 alkyl, C 2-6 alkenyl, C 3-6 cycloalkyl, C 1-6 haloalkyl, C 1-3 alkoxy, C 1-3 alkylthio, carboxy, C 1-4 alkoxycarbonyl, phenyl, or phenyl substituted 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 21 is hydrogen, C 1-4 alkyl, C 1-3 alkylthio or, together with R 20 , is -(CH 2 ) p - or -S(CH 2 ) q S-; and the salts of those compounds of formula I that have a free carboxy group.
  • Y is oxygen
  • R 1 is methoxy
  • R 2 is methoxy
  • R 5 is methyl
  • R 6 is methyl or ethyl
  • R 7 is hydrogen, hydroxy, C 1-4 alkoxy, carboxy or C 1-2 alkoxycarbonyl; or
  • Y is sulfur
  • R 1 is methoxy
  • R 2 is methoxy
  • R 5 is methyl
  • R 6 is hydrogen, methyl or ethyl
  • R 7 is hydrogen, hydroxy or C 1-4 alkoxy.
  • Q is the group Q 1 ;
  • Y is oxygen
  • R 1 and R 2 are methoxy
  • R 3 is methyl or ethyl or, together with R 4 , is -(CH 2 ) p -;
  • R 4 is C 1-3 alkyl or phenyl.
  • R 3 is methyl or ethyl and A is C 1-3 alkoxy, hydroxy, 2-propenyloxy or an inorganic or organic salt of the free acid;
  • A is (C 1-3 alkyl-oxetan-S-yl)oxy
  • A is an ⁇ S> chiral group A 1 wherein R 9 is hydrogen or, together with R 11 , is -(CH 2 ) 3 -, R 10 is a group COZ wherein Z is as defined for formula I, R 11 is hydrogen, C 1-4 alkyl or benzyl, R 12 and R 19 are hydrogen, W is oxygen or sulfur and m is the number 1; or d) A is a group A 4 wherein R 13 is C 1-4 alkyl, phenyl, or phenyl mono- or di-substituted by fluorine, chlorine, methyl, trifluoromethyl, methoxy or by nitro; or
  • A is a group A 5 wherein R 15 is C 1-4 alkyl, phenyl, or phenyl mono- or di-substituted by fluorine, chlorine or by methyl; or
  • A is an ⁇ S> chiral group A 1 wherein R 9 is hydrogen or, together with R 11 , is -(CH 2 ) 3 -, R 10 is a group COZ wherein Z is as defined for formula I and R 12 is hydrogen, Z preferably being C 1-4 alkoxy, C 3-4 alkenyloxy, amino or a group (Z 1 ) and R 11 being hydrogen, C 1-4 alkyl or benzyl.
  • Q is the group Q 1 ;
  • Y is oxygen
  • R 1 is methoxy
  • R 2 is methoxy
  • R 3 is hydrogen, methyl or ethyl or, together with R 4 , is -(CH 2 ) p -;
  • R 4 is formyl, carboxy, C 1-2 alkylcarbonyl or C 1-3 alkoxycarbonyl
  • A is hydroxy, C 1-3 alkoxy, 2-propenyloxy or an organic or inorganic salt of the free acid.
  • Q is Q 1 ;
  • Y is sulfur
  • R 1 is methoxy
  • R 2 is methoxy
  • R 3 is methyl or ethyl
  • R 4 is C 1-3 alkyl, cyclopropyl or phenyl
  • A is C 1-3 alkoxy, hydroxy or an inorganic or organic salt of the free acid
  • R 3 is hydrogen, methyl, ethyl, methylthio or, together with R 4 , is -S(CH 2 ) 2 S-;
  • R 4 is methylthio, formyl, carboxy, C 1-2 alkylcarbonyl or C 1-2 alkoxycarbonyl;
  • A is hydroxy, C 1-3 alkoxy, 2-propenyloxy or an inorganic or organic salt of the free acid; or c) R 3 is metiiyl or ethyl;
  • R 4 is C 1-3 alkyl, cyclopropyl or phenyl
  • A is (oxetan-3-yl)oxy, 2-propenyloxy or an ⁇ S> chiral group A 1 or A 2 wherein R 9 is hydrogen or, together with R 11 , is -(CH 2 ) 3 -, R 10 is a group COZ wherein Z is as defined for formula I, and R 11 is hydrogen, C 1-4 alkyl or benzyl.
  • Q is the group Q 2 ; Y is sulfur;
  • R 1 is methoxy
  • R 2 is methoxy
  • R 5 is methyl or methoxy
  • R 6 is hydrogen, methyl or ethyl
  • R 7 is hydrogen, hydroxy or C 1-4 alkoxy.
  • R 1 is methyl, methoxy or dimethylamino
  • R 2 is methoxy
  • Prominent compounds of formula I from that group are especially those wherein either a) Y is oxygen;
  • R 3 or R 5 is methyl
  • R 4 or R 6 is methyl or ethyl
  • R 7 is hydrogen, hydroxy, C 1-4 alkoxy or carboxy
  • R 3 is hydrogen or methyl
  • R 4 is C 1-2 alkoxy or C 1-2 alkoxycarbonyl
  • A is hydroxy, C 1-3 alkoxy or an organic or inorganic salt of the free acid.
  • Compounds of formula I can be prepared by reacting a pyrimidine of formula II wherein E, R 1 and R 2 are as defined for formula I and L is a leaving group such as fluorine, chlorine, bromine, methylsulfonyl, ethanesulfonyl, benzylsulfonyl, 3-C 1-4 alkylsulfonyl-1H-1,2,4-triazol-1-yl (e.g. 3-methylsulfonyl-1H-1,2,4-triazol-1-yl) with a propenoate, 2-oxo-propionate or furanone compound of foimula III, IIIa or IV, respectively,
  • R 3 , R 4 , R 5 and R 6 are as defined for formula I and R 7 is hydrogen, C 1-6 alkoxy, carboxy or C 1-4 alkoxycarbonyl
  • A is hydrogen, hydroxy, C 1-6 alkoxy, C 1-2 alkoxyC 1-2 alkoxy, C 1-2 alkylthio-C 1-2 alkoxy, C 1-2 alkylsulfinyl-C 1-2 alkoxy, C 2-4 dialkylamino-C 1-2 alkoxy, C 1-3 alkylcarbonyloxy-C 1-2 alkoxy, C 3-4 alkenyloxy, C 3-4 alkynyloxy, C 3-6 cycloalkoxy, benzyloxy or ( C 1-3 alkyl-oxetan-3-yl)oxy and Y' is hydroxy or mercapto, but especially hydroxy, in the presence of an acid-binding agent, such as n-butyllithium, sodium hydride, potassium carbonate or triethylamine, and
  • E, R 1 and R 2 are as defined for formula I, R"' is hydroxy or a leaving group and A' is C 1-6 alkoxy, C 1-2 alkoxy-C 1-2 alkoxy, C 2-6 alkenyloxy, benzyloxy or (C 1-3 alkyloxetan-3-yl)oxy, especially C 1-4 alkoxy, 2-propenyloxy or benzyloxy, and then reacting the product thereof with the corresponding electrophilic compound of formula VI, wherein R 3 and R 4 are as defined above, or with carbon disulfide or an alkylisothiocyanate, wherein R" is C 1-4 alkyl, and a subsequent corresponding alkylating agent R'X wherein R' is C 1-3 alkyl or -(CH 2 ) q - and X is methoxy- or ethoxy-sulfonyl, chlorine, bromine or iodine, or with a corresponding orthoester or dialkylaminodimethylace
  • Suitable lithiating agents are solutions of lithium diisopropylamide, bis(trimethylsilyl)-lithium amide, n-butyllithium, sec-butyllithium, tert-butyllithium or phenyllithium in hexane, heptane, isooctane or diethyl ether, especially the lithium salt of 1,1,1,3,3,3-hexamethyldisilazane or n-butyllithium in hexane.
  • R'" is hydroxy or a leaving group, and then to convert it under the dehydration conditions familiar to a person skilled in the art into the compound of formula If wherein R 1 , R 2 , E and A' are as defined above and R 3 is C 1-4 alkyl and R 4 is C 1-6 alkyl, C 2-6 alkenyl, C 3-6 cycloalkyl, C 1-6 haloalkyl, C 1-4 alkoxycarbonyl, phenyl, or phenyl substituted 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.
  • OR''' is hydroxy
  • a suitable leaving group OR' such as an acetate, mesylate or tosylate group
  • a base such as triethylamine, 1,8-diazabicyclo[5.4.0]undec-7-ene or dimethylaminopyridine
  • compounds of formula la wherein R 1 , R 2 and E are as defined above, and A' is especially hydrogen, C 1-4 alkoxy, 2-propenyloxy or benzyloxy, R 3 is hydrogen and R 4 is formyl, C 1-5 alkylcarbonyl, carboxy or C 1-4 alkoxycarbonyl can be prepared by reacting a compound of formula IX
  • That reaction is likewise advantageously carried out in the presence of an acid-binding agent, such as sodium hydride, sodium hydrogen carbonate, potassium carbonate or triethylamine, and in the presence of an inert diluent, such as tetrahydrofuran, diethoxymethane, dimethoxyethane, acetone, methyl ethyl ketone, methanol, ethanol, acetonitrile, propionitrile, dimethylformamide, N-methylpyrrolidone, 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone (DMPU) or dimethyl sulfoxide.
  • an acid-binding agent such as sodium hydride, sodium hydrogen carbonate, potassium carbonate or triethylamine
  • an inert diluent such as tetrahydrofuran, diethoxymethane, dimethoxyethane, acetone, methyl ethyl ketone,
  • A' is especially C 1-4 alkoxy, 2-propenyloxy or benzyloxy is hydrolysed under hydrolysis conditions familiar to a person skilled in the art or is cleaved by hydrogen- olysis, for example with H 2 /Pd in the case of benzyloxy, or with tris(triphenylphosphine)-rhodium(I) chloride (Wilkinson catalyst) in the case of 2-propenyloxy, to form the acid.
  • Suitable hydrolysis agents for the former case especially in the case of compounds wherein Y is oxygen, are sodium or potassium hydroxide and sodium or potassium carbonate.
  • Suitable solvents are, for example, water or mixtures of methanol/water, ethanol/water, tetrahydrofuran/water, diethoxymethane/water, dioxane/water or dimethyl formamide/water.
  • Suitable solvents for the hydrogenolytic cleavage are especially methanol, ethanol, ethyl acetate, acetic acid, trifluoroacetic acid, dioxane and water, and mixtures thereof.
  • Compounds of formula I wherein Q is Q 4 can also be prepared by heating a compound of formula lb wherein R 3 is hydrogen or C 1-4 alkyl, if desired in the presence of an agent that removes the elements of water, such as a carboxylic acid anhydride, especially acetic anhydride.
  • Compounds of formula I can also be prepared by reacting a compound of formula Ic or an anhydride of formula Id wherein E, Y, R 1 , R 2 , R 3 , R 4 , R 20 , R 21 , R 24 and R 25 are as defined above, and wherein A'" is a leaving group such as chlorine, fluorine, bromine, 2,4,6-triisopropyl-sulfonyl, imidazolyl, triazolyl, 2-thiono-thiazolidin-3-yl or N,N'-dicyclohexyl-isoureidyl, with a nucleophilic compound of formula VII wherein A is R 8 , (C 1 -3 alkyl-oxetan-3-yl)oxy or a group A 1 to A 6 , A 1 to A 6 being as defined for formula I, where appropriate in the presence of a base and of a solvent.
  • A'" is a leaving group such as chlorine, fluorine, bromine,
  • Suitable bases are especially tertiary amines, such as triethylamine, N,N-dimethylaniline, 1,8-diazabicyclo[5.4.0]undec-7-ene, imidazole, pyridine or 2,5-dimethylpyridine. They can be used in a catalytic amount, as well as in a stoichiometric amount or in excess; preferably in a stoichiometric amount or in a slight excess. A slight excess of the substrate of formula VII used is also suitable as a base.
  • Suitable solvents are hydrocarbons, such as toluene, halogenated chlorohydrocarbons, such as dichloromethane, 1,2-dichloroethane or chlorobenzene, ethers, such as diethyl ether, dimethoxyethane or tertiary butyl methyl ether, aprotic solvents, such as acetonitrile, or protic solvents, such as alcohols, especially ethanol, or water.
  • hydrocarbons such as toluene
  • halogenated chlorohydrocarbons such as dichloromethane, 1,2-dichloroethane or chlorobenzene
  • ethers such as diethyl ether, dimethoxyethane or tertiary butyl methyl ether
  • aprotic solvents such as acetonitrile
  • protic solvents such as alcohols, especially ethanol, or water.
  • it is also possible to carry out the reaction in a two-phase system such
  • Compounds of formula Ic wherein A"' is chlorine can, for example, also be prepared by reacting an acid of formula lb with a chlorinating agent such as phosphorus oxychloride, thionyl chloride, oxalyl chloride or phosgene, especially phosphorus oxychloride, in the presence of a base, such as triethylamine, dimethylaniline or pyridine, and, where appropriate, in a solvent such as a hydrocarbon, for example toluene, a chlorohydrocarbon, for example methylene chloride, or an ether, for example tetrahydrofuran, in a temperature range of from -20° to the reflux temperature of the reaction mixture, preferably at from -5°C to room temperature.
  • a chlorinating agent such as phosphorus oxychloride, thionyl chloride, oxalyl chloride or phosgene, especially phosphorus oxychloride
  • a base such as
  • the corresponding acid chloride (A'" is chlorine) or imidazolide (A"' is imidazole) can also be reacted without being isolated with the corresponding nucleophilic compound of formula VII, where appropriate in the presence of an additional base, such as triethylamine. That reaction likewise takes place in a temperature range of from approximately -20°C to the reflux temperature of the solvent used, preferably at from -5°C to room temperature.
  • an acid of formula lb first into the conesponding more stable acid anhydride of formula Id using from 0.50 to 0.55 of an equivalent of phosphorus oxychloride and a slight excess of from 2.0 to 3.0 equivalents of triethylamine and then to react the acid anhydride with the corresponding nucleophilic compound of formula V.
  • Compounds of formulae III, IIIa, IV, V, VI, VII, IX, X, XI and XII are either known or can be prepared by processes known from the literature.
  • the compounds of formula I are used in unmodified form, as obtainable from the synthesis, or, preferably, together with the adjuvants customarily employed in formulation technology and are therefore formulated in known manner e.g. into emulsifiable concentrates, directly sprayable or dilutable solutions, dilute emulsions, wettable powders, soluble powders, dusts, granules, and also encapsulations in e.g. polymer substances.
  • the methods of application such as spraying, atomising, dusting, wetting, scattering or pouring, are chosen in accordance with the intended objectives and the prevailing circumstances.
  • compositions, preparations or mixtures comprising the compound (active ingredient) of formula I and, where appropriate, one or more solid or liquid adjuvants are prepared in known manner, e.g. by homogeneously mixing and/or grinding the active ingredients with extenders, e.g. solvents, solid carriers and, where appropriate, surface-active compounds (surfactants).
  • extenders e.g. solvents, solid carriers and, where appropriate, surface-active compounds (surfactants).
  • Suitable solvents are: aromatic hydrocarbons, preferably the fractions containing 8 to 12 carbon atoms, such as mixtures of alkylbenzenes, e.g. xylene mixtures or alkylated naphthalenes; aliphatic and cycloaliphatic hydrocarbons, such as paraffins, cyclohexane or tetrahydronaphthalene; alcohols, such as ethanol, propanol or butanol; glycols and their ethers and esters, such as propylene glycol or dipropylene glycol ether; ketones, such as cyclohexanone, isophorone or diacetone alcohol; strongly polar solvents, such as N-methyl-2-pyrrolidone, dimethyl sulfoxide or water, vegetable oils and esters thereof, such as rape oil, castor oil or soybean oil; and, where appropriate, also silicone oils.
  • aromatic hydrocarbons preferably the fractions containing 8 to 12 carbon atoms, such
  • the solid carriers used are normally natural mineral fillers, such as calcite, talcum, kaolin, montmorillonite or attapulgite.
  • calcite talcum
  • kaolin kaolin
  • montmorillonite attapulgite
  • highly dispersed silicic acid or highly dispersed absorbent polymers e.g., calcite, talcum, kaolin, montmorillonite 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.
  • pregranulated materials of inorganic or organic nature can be used, e.g. especially dolomite or pulverised plant residues.
  • suitable surface-active compounds are non-ionic, canonic and/or anionic surfactants having good emulsifying, dispersing and wetting properties.
  • surfactants will also be understood as comprising mixtures of 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. Mention may also be made of fatty acid methyltaurin salts.
  • so-called synthetic surfactants are used, especially fatty alcohol sulfonates, fatty alcohol sulfates, sulfonated benzimidazole derivatives or alkylarylsulfonates.
  • the fatty alcohol 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 the alkyl moiety of acyl radicals, e.g. the sodium or calcium salt of lignosulfonic acid, of dodecyl sulfate or of a mixture of fatty alcohol sulfates obtained from natural fatty acids.
  • These compounds also comprise the salts of sulfated and sulfonated fatty alcohol/ethylene oxide adducts.
  • the sulfonated benzimidazole derivatives preferably contain two 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 the phosphoric acid ester of an adduct of p-nonylphenol with 4 to 14 mol of ethylene oxide, or phospholipids.
  • Non-ionic surfactants are preferably polyglycol ether derivatives of aliphatic or cycloaliphatic 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) hydrocarbon 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 with 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 ether 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 nonylphenol polyethoxyethanols, castor oil polyglycol ethers, polypropylene/polyethylene oxide adducts, tributylphenoxypolyethoxyethanol, polyethylene glycol and octylphenoxypolyethoxyethanol.
  • Fatty acid esters of polyoxyethylene sorbitan e.g. polyoxyethylene sorbitan trioleate, are also suitable non-ionic surfactants.
  • Cationic surfactants are preferably quaternary ammonium salts which contain, as
  • the salts are preferably in the form of halides, methyl sulfates or ethyl sulfates, e.g. stearyltrimethylammonium chloride or benzyldi(2-chloroethyl)ethylammonium bromide.
  • the herbicidal compositions usually comprise 0.1 to 99 %, preferably 0.1 to 95 %, of a compound of formula 1, 1 to 99 % of a solid or liquid adjuvant, and 0 to 25 %, preferably 0.1 to 25 %, of a surfactant.
  • compositions may also comprise further auxiliaries, such as stabilisers, e.g. vegetable oils or epoxidised vegetable oils (epoxidised coconut oil, rape oil or soybean oil), anti-foams, e.g. silicone oil, preservatives, viscosity regulators, binders and tackifiers, as well as fertilisers or other active ingredients for obtaining special effects.
  • stabilisers e.g. vegetable oils or epoxidised vegetable oils (epoxidised coconut oil, rape oil or soybean oil)
  • anti-foams e.g. silicone oil
  • preservatives e.g. silicone oil
  • viscosity regulators e.g. binders and tackifiers
  • fertilisers or other active ingredients for obtaining special effects.
  • Prefened formulations have especially the following composition (throughout, percentages are by weight)
  • Emulsifiable concentrates are:
  • active ingredient 1 to 90 %, preferably 5 to 20 %
  • surface-active agent 1 to 30 %, preferably 10 to 20 %
  • liquid carrier 5 to 94 %, preferably 70 to 85 %
  • active ingredient 0.1 to 10 %, preferably 0.1 to 1 %
  • solid carrier 99.9 to 90 %, preferably 99.9 to 99 %
  • active ingredient 5 to 75 %, preferably 10 to 50 %
  • surface-active agent 1 to 40 %, preferably 2 to 30 %
  • active ingredient 0.5 to 90 %, preferably 1 to 80 %
  • surface-active agent 0.5 to 20 %, preferably 1 to 15 %
  • active ingredient 0.5 to 30 %, preferably 3 to 15 %
  • solid carrier 99.5 to 70 %, preferably 97 to 85 %
  • the compounds of formula I are generally used successfully at rates of application of from 0.001 to 3 kg/ha, especially from 0.005 to 1 kg/ha.
  • concentration required to achieve the desired effect can be determined by experiment It is dependent upon the type of action, the stage of development of the cultivated plant and of the weed, and also upon the application (place, time, method) and, in dependence on those parameters, can vary within wide limits.
  • the compounds of formula I are distinguished by growth-inhibiting and herbicidal properties, which render them excellently suitable for use in crops of useful plants, especially in cereals, cotton, soybeans, rape, maize, sugar beet and rice.
  • the invention relates also to herbicidal compositions comprising a novel compound of formula I, and to methods of inhibiting plant growth.
  • Example P8 Preparation of 2-f(4.6-dimethoxy-pyrimidin-2-yl)thio]-3-methyl-2-pentenoic acid ethyl ester (Example 2.028):
  • a suspension of 14.1 g of mucochloric acid in 250 ml of water is neutralised at room temperature with 7.0 g of sodium hydrogen carbonate.
  • a suspension of 14.4 g of 4,6-dimethoxy-2-mercaptopyrimidine is treated with a solution of 3.3 g of sodium hydroxide in water and then in the form of a yellowish solution is added dropwise to the above solution in the course of 40 minutes at a temperature of 0°C.
  • the reaction mixture is stirred for a further hour at 0°C and then is adjusted to pH 3 with 2N hydrochloric acid.
  • test compounds are preferably formulated as emulsifiable concentrates (EC) and are diluted wi ⁇ water to the desired concentration immediately before application.
  • Insoluble compounds are formulated as wettable powders (WP) using kaolin as inert carrier. The wettable powder is suspended in water immediately before application.
  • the concentrations in g of active ingredient/hectare relate to the surface of the soil in the containers, unless otherwise indicated.
  • the spray volume is 10001/ha (corresponding to 100 ml/m 2 ).
  • the seeds of the plants are sown in plastics plant pots of various sizes containing heatsterilised (steam-treated) soil (earth 2.6 % peat, 20 % clay, 30 % coarse clay, 47 % sand).
  • the plants are kept in a greenhouse at a moderate temperature (17 - 25°C in winter, 18 -35°C in summer) (humidity 30 - 90 %).
  • the length of the illumination period is from 13 to 16 hours/day; if necessary artificial light is provided (15 000 to 18000 lux).
  • the artificial illumination is also activated automatically when there is insufficient daylight intensity.
  • Table B1 Examples of the good herbicidal action of the compounds of formula I described in Tables 1-3 of the present Application are listed in Table B1: Table B1: Pre-emergence herbicidal action:
  • SORG Sorghum halepense Johnson grass
  • ECHI Echinochloa crus-galli Barnyard grass
  • MATR Matricaria chamomilla Wild Chamomile
  • CASS Cassia ohtusifolia Sicklepod Biological Example B2 was carried out to test the herbicidal activity of the compounds of the present Application in comparision with that of compounds from the prior art
  • a number of weeds, both monocotyledonous and dicotyledonous, are treated post-emergence (in the 2- to 6-leaf stage) with an aqueous active ingredient dispersion at a rate of 3 kg of active ingredient per hectare.
  • test compounds are preferably formulated as emulsifiable concentrates (EC) and are diluted with water to the desired concentration immediately before application.
  • Insoluble compounds are formulated as wettable powders (WP) using kaolin as inert carrier. The wettable powder is suspended in water immediately before application.
  • the concentrations in g of active ingredient/hectare relate to the surface of the soil in the containers, unless otherwise indicated.
  • the spray volume is 5001/ha.
  • the seeds of the plants are sown in plastics plant pots of various sizes containing heat-sterilised (steam-treated) soil (' Optima' earth 80 % peat, 20 % loess).
  • the plants are kept in a greenhouse at a moderate temperature (17 - 25°C in winter, 18 - 35°C in summer) (humidity 30 - 90 %).
  • the length of the illumination period is from 13 to 16 hours/day; if necessary artificial light is provided (15000 to 18000 lux).
  • the artificial illumination is also activated automatically when there is insufficient daylight intensity.
  • Table B2 Post-emergence herbicidal action
  • SORG Sorghum halepense Johnson grass
  • ECHI Echinochloa crus-galli Barnyard grass
  • DATU Datura Stramonium Jimsonweed
  • CASS Cassia obtusifolia Sicklepod

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  • Organic Chemistry (AREA)
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Abstract

L'invention concerne des ethers et des thioethers de pyrimidinyle et de triazinyle de formule (I) dans laquelle Q représente (Q1), (Q2), (Q3); les autres définitions des substituants sont données dans la revendication 1. L'invention se rapporte également aux sels des composés de formule (I). Lesdits composés présentent une activité herbicide et sont utilisables comme ingrédients actifs dans des compositions destinées à éliminer les mauvaises herbes.
EP92923193A 1991-10-11 1992-11-03 Composes de pyrimidinyle et de triazinyle a activite herbicide Withdrawn EP0629192A1 (fr)

Applications Claiming Priority (2)

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CH298891 1991-10-11
PCT/EP1992/002516 WO1994010156A1 (fr) 1991-10-11 1992-11-03 Composes de pyrimidinyle et de triazinyle a activite herbicide

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GB8912700D0 (en) * 1989-06-02 1989-07-19 Shell Int Research Herbicidal compounds
DE3924260A1 (de) * 1989-07-19 1991-01-31 Schering Ag Substituierte pyrimidinyloxy(thio)- und triazinyloxy(thio)-acrylsaeurederivate, verfahren zu ihrer herstellung und ihre verwendung als mittel mit herbizider, fungizider und pflanzenwachstumsregulierender wirkung
DE3924259A1 (de) * 1989-07-19 1991-01-31 Schering Ag Substituierte (alpha)-pyrimidinyloxy(thio)- und (alpha)-triazinyloxy(thio)carbonsaeurederivate, verfahren zu ihrer herstellung und ihre verwendung als mittel mit herbizider, fungizider und pflanzenwachstumsregulierender wirkung

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