WO2001017973A2 - Neue herbizide - Google Patents

Neue herbizide Download PDF

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WO2001017973A2
WO2001017973A2 PCT/EP2000/008657 EP0008657W WO0117973A2 WO 2001017973 A2 WO2001017973 A2 WO 2001017973A2 EP 0008657 W EP0008657 W EP 0008657W WO 0117973 A2 WO0117973 A2 WO 0117973A2
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substituted
halogen
alkyl
alkoxy
formula
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PCT/EP2000/008657
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German (de)
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French (fr)
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WO2001017973A3 (de
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Thomas Maetzke
Sebastian Wendeborn
André Stoller
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Syngenta Participations Ag
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Priority to PL00356456A priority Critical patent/PL356456A1/xx
Priority to AU75146/00A priority patent/AU7514600A/en
Priority to EP00964108A priority patent/EP1230245A2/de
Priority to HU0202844A priority patent/HUP0202844A3/hu
Priority to CA002382432A priority patent/CA2382432A1/en
Publication of WO2001017973A2 publication Critical patent/WO2001017973A2/de
Publication of WO2001017973A3 publication Critical patent/WO2001017973A3/de

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04—Ortho-condensed systems
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having no bond to a nitrogen atom
    • A01N47/06—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having no bond to a nitrogen atom containing —O—CO—O— groups; Thio analogues thereof
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
    • A01N47/18—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing a —O—CO—N< group, or a thio analogue thereof, directly attached to a heterocyclic or cycloaliphatic ring
    • 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
    • A01N53/00—Biocides, pest repellants or attractants, or plant growth regulators containing cyclopropane carboxylic acids or derivatives thereof
    • 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
    • A01N55/00—Biocides, pest repellants or attractants, or plant growth regulators, containing organic compounds containing elements other than carbon, hydrogen, halogen, oxygen, nitrogen and sulfur
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C07C323/50—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton
    • C07C323/62—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/612—Esters of carboxylic acids having a carboxyl group bound to an acyclic carbon atom and having a six-membered aromatic ring in the acid moiety
    • C07C69/616—Esters of carboxylic acids having a carboxyl group bound to an acyclic carbon atom and having a six-membered aromatic ring in the acid moiety polycyclic
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/62—Halogen-containing esters
    • C07C69/65—Halogen-containing esters of unsaturated acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three 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, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D231/28—Two oxygen or sulfur atoms
    • C07D231/30—Two oxygen or sulfur atoms attached in positions 3 and 5
    • C07D231/32—Oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/0803—Compounds with Si-C or Si-Si linkages
    • C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/0803—Compounds with Si-C or Si-Si linkages
    • C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
    • C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring

Definitions

  • the present invention relates to new, herbicidally active pyrazolinone derivatives, processes for their preparation, compositions which comprise these compounds and their use for controlling weeds, especially in crops of useful plants or for inhibiting plant growth.
  • the present invention thus relates to compounds of the formula I.
  • Ri and R 3 independently of one another hydrogen, halogen, nitro, cyano, -CC 4 alkyl, C 2 -C 4 -
  • R 2 is phenyl, naphthyl or a 5- or 6-membered aromatic ring which is 1 or 2
  • Heteroatoms selected from the group containing nitrogen, oxygen and sulfur can, wherein the phenyl ring, the naphthyl ring and the 5- or 6-membered aromatic ring by halogen, C 3 -C 8 cycloalkyl, hydroxy, mercapto, amino, amino-CrC 6 -alkyl, carboxyl -C-C 6 -alkyl , Cyano, nitro or formyl may be substituted; and / or the phenyl ring, the naphthyl ring and the 5- or 6-membered aromatic ring by dC 6 - alkyl, -C-C 6 alkoxy, hydroxy-d-Ce-alkyl, Ci-Ce-alkoxy-CrCe-alkyl, dC 6 -alkoxy-C ⁇ -C 6 - alkoxy, dC 6 -alkylcarbonyl, dC 6 -alkylthio, CrC 6 -alkyl
  • R5 2 , R 5 3, Rw and R 55 independently of one another hydrogen, dC 6 alkyl, C 2 -C 6 alkenyl or C 3 -C 6 alkynyl or by halogen, hydroxy, alkoxy, mercapto, amino, cyano, nitro , Alkylthio, alkylsulfinyl or alkylsulfonyl substituted d-C ⁇ -alkyl, C 2 -C 6 alkenyl or C 3 -C 6 alkynyl,
  • R and R 5 are independently hydrogen, d-C ⁇ 2 -alkyl, C 2 -Halogenalky
  • R 4 and R 5 together with the atoms to which they are attached form a 5- to 8-membered group
  • Form ring which may contain 1 or 2 oxygen atoms, sulfur atoms or groups NR 6 , wherein
  • R 6 is hydrogen, dC 4 alkyl, dC 6 alkylcarbonyl, C ⁇ -C 6 alkylsulfonyl, C 3 -C 6 alkenyl or
  • Haloalkyl, C 3 -C 8 cycloalkyl, phenyl or benzyl may be substituted; or with halogen, dC 6 -alkyl, dC 6 -haloalkyl, C 3 -C 6 -cycloalkyl, hydroxy, -C-C 6 -alkoxy,
  • C 1 -C 6 -alkoxy-C 6 -C 6 alkoxy, dC ⁇ -haloalkoxy or nitro substituted phenyl or with Halogen, C ⁇ -C6 alkyl, Ci-Ce-haloalkyl, C 3 -C 6 alkoxy, Ci-Ce-haloalkoxy or nitro substituted benzyl may be substituted 6 -cycloalkyl, hydroxy, C ⁇ -C; or with CH 2 heteroaryl, the aryl part having 5 or 6 members, or with halogen, Ci-Ce alkyl, Ci-Ce haloalkyl, dC 6 cycloalkyl, hydroxy, Ci-Ce alkoxy, dC 6 -Halogenalkoxy or nitro substituted CH 2 heteroaryl, where the aryl part is 5- or 6-membered, may be substituted; or the heteroaryl substituted with heteroaryl, the aryl part being 5- or 6-membered, or with
  • G is hydrogen, -C (X ⁇ ) -R 30 , -C (X 2 ) -X 3 -R 3 ⁇ , -C (X 4 ) -N (R 32 ) -R 33 , -SOa-R ⁇ , an alkali -, alkaline earth metal, sulfonium or ammonium cation, -P (X 5 ) (R35) -R36 or -CH 2 X6C (X 7 ) -R 37l -CH 2 X 8 C (X 9 ) -X ⁇ 0 - R 8, -CH 2 X ⁇ C (X ⁇ 2 ) -N (R 3 9) -R o or -CH 2 X ⁇ 3 SO 2 -R 4 ⁇ , wherein X 1 t X 2 , X 3 , X 4 , X 5 , X 6 , X 7 , X 8 X 9 , X 1 0, Xu, X 12 and
  • R36, R37, R38, R39, R 4 o and R 4 ⁇ independently of one another hydrogen, C1-C12-alkyl or with halogen, formyl, cyano, nitro, tri- CrC 6 -alkylsilyl, hydroxy, C ⁇ -C 6 -alkoxy, d-C 6 -alkoxycarbonyl, amino, -C-C 6 -alkylamino, di-dC 6 -alkylamino, mercapto, dC 6 - alkylthio, dC 6 -alkylcarbonyl, C ⁇ Ce-alkylcarbonylthio, C ⁇ -C 6 -alkylcarbonylamino, dC 6 - alkoxycarbonylamino, C ⁇ -C 6 alkylaminocarbonylamino, Ci-Ce-alkylthiocarbonyloxy, CC 6 - alkylthiocarbonylamino, d-C ⁇ -alk
  • R M additionally C 2 -C 20 alkenyl or with halogen, dC 6 -alkylcarbonyl, CrC 6 -alkoxycarbonyl, Ci-Ce-alkylcarbonyloxy, -C-C 6 -alkoxy, C ⁇ -C 6 -thioalkyl, C ⁇ -C 6 -alkylthiocarbonyl , dC 6 - alkylcarbonylthio, -C-C 8 alkylsulfonyl, C ⁇ -C 6 -alkylsulfinyl, Ci-Ce-alkylaminosulfonyl, di-C Ce-alkylaminosulfonyl, dC 6 -alkylsulfonyloxy, C ⁇ -C 6 -alkylsulfonylamino, C ⁇ -C 6 - alkylamino, di- C ⁇ -C 6 -alkylamino, C ⁇ -C 6 alkylcarbonyla
  • Ci-Ce-alkylcarbonyl Ci-Ce-alkylcarbonyl, dC 6 -alkoxycarbonyl, Ci-Ce- alkylcarbonyloxy, -C-C 6 -alkoxy, C ⁇ -C 6 -thioalkyl, CrC ⁇ -alkylthiocarbonyl, C ⁇ -C 6 - alkylcarbonylthio, Ci-Ce-alkylsulfonyl, d-Ce-alkylsulfinyl, -C-C 6 -alkylaminosulfonyl, di- d- C 6 -alkylaminosulfonyl, CrC 6 -alkylsulfonyloxy, C ⁇ -C 6 -alkylsulfonylamino, -C ⁇ -C 6 alkylamino , C 1 -C 6 alkylamino, CrC 6 alkylcarbonylamino,
  • alkyl groups occurring in the substituent definitions can be straight-chain or branched and are, for example, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, pentyl and hexyl and branched Isomers thereof.
  • Suitable alkenyl and alkynyl groups as well as alkoxy and allylthio groups and other groups containing an alkyl unit are derived from the alkyl groups mentioned.
  • cycloalkyl groups which are suitable according to the invention are cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl and cyclooctyl.
  • Halogen substituents are preferably fluorine, chlorine or bromine.
  • 5- and 6-membered aromatic rings with heteroatoms are thiophenyl, furanyl and pyridinyl.
  • Examples of 5- to 8-membered heteroaryls and heterocycloalkyls are pyrazolidine, 1, 2,3,6-tetrahydropyridazine, hexahydropyridazine, 1, 4,5-oxadiazepane, 1, 4,5-thiadiazepane and 1, 4,5-oxadiazoxane call.
  • the invention also encompasses the salts which the compounds of the formula I can preferably form with amines, alkali metal and alkaline earth metal bases or quaternary ammonium bases.
  • Suitable salt formers are described, for example, in WO98 / 41089.
  • the invention also includes the salts which the compounds of formula I can form with amines, alkali and alkaline earth metal bases or quaternary ammonium bases.
  • alkali and alkaline earth metal hydroxides as salt formers, the hydroxides of lithium, sodium, potassium, magnesium or calcium should be emphasized, but especially those of sodium or potassium.
  • Examples of amines suitable for the formation of ammonium salt include both ammonia and also primary, secondary and tertiary C 1 -C 8 -alkylamines, C 1 -C 4 -hydroxyalkylamines and C 2 -C -alkoxyalkylamines, for example methylamine, ethylamine, n-propylamine, iso -Propylamine, the four isomeric butylamines, n-amylamine, iso-amylamine, hexylamine, heptylamine, octylamine, nonylamine, decylamine, pentadecylamine, hexadecylamine, heptadecylamine, octadecylamine, methylethylamine, methyl-iso-propylamine, methylhexylamine, methyl nonylamine, methylpentadecylamine, methyl
  • Preferred quaternary ammonium bases which are suitable for salt formation correspond, for example, to the formula [N (R a R b R c Rd)] OH, where R a , R, R c and R d independently of one another are C 1 -C 4 alkyl.
  • R a , R, R c and R d independently of one another are C 1 -C 4 alkyl.
  • Other suitable tetraalkylammonium bases with other anions can be obtained, for example, by anion exchange reactions.
  • R 1 and R 3 are, independently of one another, dC-alkyl, in particular methyl or ethyl, C 2 -C -alkynyl, in particular ethynyl, C 1 -C 6 -alkoxy, in particular methoxy, dd-alkylthio, in particular Methylthio, C 1 -C 6 -haloalkyl, in particular chloromethyl and chloroethyl, formyl, C 1 -C 4 -alkylcarbonyl, in particular acetyl, or CC 4 -alkylamino or di- (C 1 -C 4 ) -alkylamino.
  • methyl, ethyl, ethynyl and methoxy are particularly preferred.
  • R 2 is phenyl, 2-thiophenyl, 3-thiophenyl, 2-furanyl, 3-furanyl, 2-pyridinyl, 3-pyridinyl or 4-pyridinyl, phenyl being particularly preferred.
  • the corresponding substituted ring systems are also preferred, the substituents being halogen, hydroxy, mercapto, amino, cyano, nitro, formyl, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl and C 3 -C 8 -cycloalkyl.
  • R 4 and R 5 are independently C ⁇ -Ci2-alkyl, d-C ⁇ -C ⁇ 0 alkoxy-C 8 -alkyl or C 3 -C 8 -alkyl which one or can contain two oxygen atoms, or R and R 5 together with the atoms to which they are attached form a saturated, 5- to 8-, in particular 6- or 7- membered ring.
  • R 4 and R 5 together form a radical -CH 2 CH 2 -O-CH2CH2- or - (CH 2 ) 4 -, these radicals with C 1 -C 10 -alkyl, dC 10 alkoxy, d-C ⁇ -alkoxy -CrCe alkoxy or hydroxyl can be substituted and a 2 to 6 Carbon atoms can contain alkylene or alkenylene chain, which can be interrupted by oxygen.
  • Further preferred compounds of the formula I have, as substituents G, hydrogen or COR 30 , in particular pivaloyl, C (O) X 3 R 3 or in which X 3 is oxygen or sulfur, R 3i -CC 2 -alkyl, d -CC 2 -haloalkyl, C 2 -C 12 -alkenyl, d -CC 2 -alkoxyalkyl, C 3 -C 2 -cycloalkyl or phenyl, and R M -C-C 6 alkyl, Ci-Ce-haloalkyl, phenyl, phenyl substituted with chlorine, cyano or methyl; or heteroaryl or heteroaryl substituted with chlorine, cyano or methyl.
  • R 1 and R 3 are, independently of one another, C 1 -C 4 -alkyl, in particular methyl or ethyl, C 2 -C -alkynyl, in particular ethynyl, CrC 6 -alkoxy, in particular methoxy or C 1 - C 4 alkylthio, especially methylthio
  • R 2 is phenyl, 2-thiophenyl, 3-thiophenyl, 2-furanyl or 3-furanyl
  • R 4 and R 5 are independently C 1 -C 2 alkyl or R and R 5 together with the atoms to which they are attached, a radical -CH 2 CH 2 -O-CH 2 CH 2 - or - (CH 2 ) -, these radicals with -C-C ⁇ o-alkyl or C ⁇ -C 6 -alkoxy-C ⁇ -C 6 -alkoxy can be substituted and
  • G is hydrogen or COR 30 , in particular piva
  • the compounds of the formula I can be prepared by processes known per se, for example described in WO97 / 02243 or the references mentioned below, for example by introducing the aromatic ring R 2 through Pd (0) -catalyzed cross-coupling of aromatic tin compounds such as, for example, phenyltin trialkyl compounds , (Stille, JK Angew. Chem. Int. Ed. Engt. 1986, 25, 508. Kwon, HB; McKee, BH; Stille, JKJ Org. Chem. 1990, 55, 3114), or zinc compounds such as phenyl zinc halides (Negishi, E .; Valente, LF; Kobayashi, MJ Am. Chem. Soc. 1980.
  • aromatic tin compounds such as, for example, phenyltin trialkyl compounds , (Stille, JK Angew. Chem. Int. Ed. Engt. 1986, 25, 508. Kwon, HB; McKee, BH; Still
  • aromatic boric acids such as Furanyl boric acids (Miyaura; N .; Yanagi, T .; Suzuki, A. Synth. Commun. 1981, 11, 513), or aromatic boric acid esters such as phenyl boric acid dialkyl esters (Sato, M .; Miyaura, N .; Suzuki, A. Chem. Lett. 1989, 1405. Watanabe, T .; Miyaura, N .; Suzuki, A.
  • R 7 - R 0 can be hydrogen and / or alkyl, in particular Ci-Ce-alkyl, and / or aryl, preferably phenyl and naphthyl.
  • the malonic ester IV or the malondiamide V can be prepared, for example, by Pd (0) -catalyzed cross-coupling according to the following scheme:
  • R 1t R 2 and R 3 have the meaning given under formula I and Hai represents chlorine, bromine or iodine, in the presence of an inert solvent, a base and a palladium catalyst at temperatures of 30 to 250 ° C.
  • the reaction is preferably carried out under an inert gas atmosphere.
  • the compounds of the formula XXX are known or by known processes, as described, for example, in J. Chem. Soc. Perkin Trans. 1 (1987), (4), 877-884.
  • the compounds of formula VIII can, for example, by known methods such as. Sandmeyer reaction from the corresponding anilines of the formula VI
  • R 1 and R 3 have the meanings given under formula I, via which diazonium salts are prepared.
  • Such reactions are described, for example, in Vogel's Textbook of Practical Organic Chemistry, 5th Edition, BS Furniss, AJ Hannaford, PWG Smith, AR Tatchell; Longman Scientific & Technical 1989, page 923.
  • the Compounds of the formula VI are known, some are commercially available or can be prepared analogously to known ones.
  • Bases such as tri-alkali metal phosphates, alkali and alkaline earth metal hydrides, alkali and alkaline earth metal amides or alkali metal alcoholates, for example tri-potassium phosphate, sodium hydride, lithium diisopropylamide (LDA), sodium tert-butoxide or K-tert-butoxide are suitable for this reaction.
  • tri-potassium phosphate sodium hydride, lithium diisopropylamide (LDA), sodium tert-butoxide or K-tert-butoxide
  • Na-tert-butoxide, K-tert-butoxide and tripotassium phosphate are particularly preferred.
  • Suitable solvents include aromatic hydrocarbons such as e.g. Xylene or toluene, ethers such as tetrahydrofuran, dioxane or ethylene glycol dimethyl ether, dimethyl sulfoxide or tertiary amides such as dimethylformamide, N-methylpyrrolidinone or dimethylacetamide or acyclic ureas such as N, N'-dimethylpropylene urea.
  • aromatic hydrocarbons such as e.g. Xylene or toluene
  • ethers such as tetrahydrofuran, dioxane or ethylene glycol dimethyl ether
  • dimethyl sulfoxide or tertiary amides such as dimethylformamide, N-methylpyrrolidinone or dimethylacetamide or acyclic ureas such as N, N'-dimethylpropylene urea.
  • the palladium catalysts which are suitable for the CC linkage reaction of a compound of the formula XXX with a compound of the formula VIII are generally palladium (II) or palladium (0) complexes such as, for example, palladium (II) dihalides, palladium (II) acetate , Palladium (ll) sulfate, bis (triphenylphosphine) palladium (ll) dichloride, bis (tricyclopentylphosphine) palladium (ll) dichloride, bis (tricyclohexylphosphine) palladium (ll) dichloride, bis ( dibenzylidene acetone) palladium (0) or tetrakis (triphenylphosphine) - palladium (O).
  • palladium (II) dihalides palladium (II) acetate , Palladium (ll) sulfate
  • the palladium catalyst can also be prepared from palladium (II) or palladium (O) compounds by complexation with the desired ligands 'in situ', for example by the palladium (II) salt to be complexed, for example palladium (II) dichloride (PdCI 2 ) or palladium (II) acetate (Pd (OAc) 2 ) together with the desired ligand, for example triphenylphosphine (PPh 3 ), tricyclopentylphosphine or tricyclohexylphosphine together with the selected solvent, a compound of formula VIII, a compound of formula XXX and base is presented.
  • the palladium (II) salt for example palladium (II) dichloride (PdCI 2 ) or palladium (II) acetate (Pd (OAc) 2
  • PdCI 2 palladium (II) acetate
  • Pd (OAc) 2 palladium (OAc) 2
  • Bidendate ligands are also possible, such as, for example, 1,1 'bis (diphenylphosphino) ferrocene or 1,2-bis (diphenylphosphino) ethane.
  • the palladium (II) or palladium (O) complex desired for the CC coupling reaction is formed 'in situ', which then starts the CC coupling reaction.
  • the palladium catalysts are used in an amount of 0.001-50 mol%, preferably in an amount of 0.1-15 mol%, based on the compound of the formula VIII.
  • the reaction temperatures are chosen depending on the solvent used and, if appropriate, the pressure.
  • the reaction is preferably carried out at atmospheric pressure.
  • type compounds can be cyclized by aminal formation with aldehydes (here with formaldehyde). Ic is like by reaction of hydrazinal carbons
  • R 0 is COOR 7 , COOR 8 , CONR 7 R, CONR 8 R ⁇ o or Cyano and R ⁇ is hydrogen, COOR 7 , COOR 8 , CONR 7 R 9 , CONR 8 R ⁇ 0 or Cyano, and R 7 ⁇ R 8 , R 9 and Rio and R 1f R 2 and R 3 have the meaning given above, where Ri and R 3 are not simultaneously hydrogen.
  • Preferred intermediates correspond to the formulas
  • R 1f R 2 and R 3 have the meanings given above, and shark is chlorine, bromine or iodine, where shark is different from iodine if Ri and R 3 are methyl and R 2 is phenyl.
  • Hydrazine components required for the compounds according to the invention can be prepared by a new process. This is therefore also the subject of the present invention.
  • This process is characterized in that the last stage in anhydrous alcohol is carried out directly with anhydrous hydrohalic acid or with in situ generated hydrohalic acid, for example from the action of methanol on acetyl chloride.
  • the hydrohalic acid can be generated by reacting anhydrous alcohol such as methanol with an acyl halide such as acetyl halide.
  • anhydrous alcohol such as methanol
  • an acyl halide such as acetyl halide.
  • Preferred hydrohalic acid is hydrochloric acid.
  • aprotic, inert organic solvents are hydrocarbons such as benzene, toluene, xylene or cyclohexane, chlorinated hydrocarbons such as dichloromethane, trichloromethane, carbon tetrachloride or chlorobenzene, ethers such as diethyl ether, ethylene glycol dimethyl ether, diethylene glycol dimethyl ether, tetrahydrofuran or dioxane, nitriles such as acetonitrile, aminopropyl amine, nitrile such as acetonitrile or amine propylene nitrate such as acetonitrile or form Diethylformamide or N-methylpyrrolidinone.
  • hydrocarbons such as benzene, toluene, xylene or cyclohexane
  • chlorinated hydrocarbons such as dichloromethane, trichloromethane, carbon tetrachloride
  • the reaction temperatures are preferably between -20 ° C and + 120 ° C.
  • the reactions are generally slightly exothermic and can usually be carried out at room temperature.
  • To the Shortening the reaction time or also to initiate the reaction can optionally be warmed up to the boiling point of the reaction mixture for a short time.
  • the reaction times can also be shortened by adding a few drops of base as the reaction catalyst.
  • Bases include, in particular, tertiary amines such as trimethylamine, triethylamine, quinuclidine, 1,4-diazabicyclo [2.2.2] octane, 1,5-diazabicyclo [4.3.0] non-5-ene or 1,5-diazabicyclo [5.4. 0] undec-7-en suitable.
  • inorganic bases such as hydrides such as sodium or calcium hydride, hydroxides such as sodium or potassium hydroxide, carbonates such as sodium and potassium carbonate or hydrogen carbonates such as potassium and sodium hydrogen carbonate can also be used as bases.
  • the compounds of the formula I can be isolated in a conventional manner by concentrating and / or evaporating the solvent and purified by recrystallizing or triturating the solid residue in solvents in which they do not dissolve well, such as ethers, aromatic hydrocarbons or chlorinated hydrocarbons.
  • the active ingredient is drawn up in solution onto mineral granulate carriers or polymerized granules (urea / formaldehyde) and dried. If necessary, a coating can also be applied (coating granules), which allows the active ingredient to be dispensed in doses over a certain period of time.
  • the compounds of formula I can be used in unchanged form, i.e. as they arise in the synthesis, are used as herbicides. However, they are preferably processed in the customary manner with the auxiliaries customary in formulation technology, e.g. to emulsifiable concentrates, directly sprayable or dilutable solutions, diluted emulsions, wettable powders, soluble powders, dusts, granules or microcapsules. Such formulations are described for example in WO 97/34485 on pages 9 to 13.
  • the application methods such as spraying, atomizing, dusting, wetting, scattering or pouring, are chosen in the same way as the type of agent, the intended goals and the given conditions.
  • the formulations ie the agents, preparations or compositions comprising the active ingredient of the formula I or at least one active ingredient of the formula I and generally one or more solid or liquid formulation auxiliaries are produced in a known manner, for example by intimately mixing and / or grinding the active ingredients with the formulation auxiliaries, such as, for example, solvents or solid carriers.
  • formulation auxiliaries such as, for example, solvents or solid carriers.
  • surface-active compounds surfactants
  • solvents and solid carriers are given, for example, in WO 97/34485 on page 6.
  • suitable surface-active compounds are nonionic, cationic and / or anionic surfactants and surfactant mixtures with good emulsifying, dispersing and wetting properties.
  • suitable anionic, nonionic and cationic surfactants are listed, for example, in WO 97/34485 on pages 7 and 8.
  • the surfactants commonly used in formulation technology which include in "Mc Cutcheon's Detergents and Emulsifiers Annual" MC Publishing Corp., Ridgewood New Jersey, 1981, Stumbleen, H., “Tensid-Taschenbuch", Carl Hanser Verlag, Kunststoff / Vienna, 1981 and M. and J. Ash, "Encyclopedia of Surfactants ", Vol III, Chemical Publishing Co., New York, 1980-81, are suitable for the preparation of the herbicidal compositions according to the invention.
  • the herbicidal formulations generally contain 0.1 to 99% by weight, in particular 0.1 to 95% by weight, of herbicide, 1 to 99.9% by weight, in particular 5 to 99.8% by weight, of a solid or liquid formulation auxiliary and 0 to 25% by weight, in particular 0.1 to 25% by weight, of a surfactant. While concentrated products are preferred as a commodity, the end user generally uses diluted products.
  • the agents can also contain other additives such as stabilizers e.g. optionally epoxidized vegetable oils (epoxidized coconut oil, rapeseed oil or soybean oil), defoamers, e.g. Contain silicone oil, preservatives, viscosity regulators, binders, adhesives as well as fertilizers or other active ingredients.
  • the active compounds of the formula I are generally applied to the plant or its habitat at a rate of from 0.001 to 4 kg / ha, in particular from 0.005 to 2 kg / ha.
  • the dosage required for the desired effect can be determined by experiment. It depends on the type of action, the stage of development of the crop and the weed, and on the application (place, time, method) and, depending on these parameters, can vary within wide ranges.
  • the compounds of the formula I are distinguished by herbicidal and growth-inhibiting properties which they have for use in crops of useful plants, in particular in Enable cereals, cotton, soybeans, sugar beets, sugar cane, plantations, rapeseed, maize and rice as well as for non-selective weed control. Cultures are also to be understood as meaning those which have been made tolerant to herbicides or herbicide classes by conventional breeding or genetic engineering methods, such as, for example, IMI Maize, Poast Protected Maize, Liberty Link Maize, Bt / Liberty Link Maize, IMI / Liberty Link Maize, IMI / Liberty Link / Bt Maize, Roundup Ready Maize and Roundup Ready / Bt Maize.
  • the weeds to be controlled can be both monocotyledonous and dicotyledonous weeds, such as, for example, Stellaria, Nasturtium, Agrostis, Digitaria, Avena, Setaria, Sinapis, Lolium, Solanum, Echinochloa, Scirpus, Monochoria, Sagittaria, Bromus, Alopecurus, Sorghum halepense, Rottboellia, Cyperus, Abutilon, Sida, Xanthium, Amaranthus, Chenopodium, Ipomoea, Chrysanthemum, Galium, Viola and Veronica.
  • Stellaria Nasturtium, Agrostis, Digitaria, Avena, Setaria, Sinapis, Lolium, Solanum, Echinochloa, Scirpus, Monochoria, Sagittaria, Bromus, Alopecurus, Sorghum halepense, Rottboellia, Cyperus, Abutilon,
  • the compound of formula I can be used advantageously with a number of other known herbicides, preferably selected from the groups of the sulfonylureas, ureas, chloroacetanilides, chloroacetamides, diphenyl ethers, nitroanilines, oxadiazolones, pyrazoles, triazines, (hetero) aryloxypropionic acids, carbamates, thiocarbamates Mix, thiatriazines, cyclohexanediones, imidazolinones, triazolopyrimidine sulfonamides, pyrimidinyloxypyridinecarboxylic acids, pyrimidinyloxybenzoic acids.
  • other known herbicides preferably selected from the groups of the sulfonylureas, ureas, chloroacetanilides, chloroacetamides, diphenyl ethers, nitroanilines, oxadiazolones,
  • the mixing partners of the compound of formula I can optionally also be in the form of esters or salts, such as z. B. in The Pesticide Manual, Eleventh Edition, 1997, BCPC.
  • the compound of formula I and mixtures thereof with the other herbicides mentioned above can also be used in combination with safeners.
  • safeners are preferably suitable: a compound of the formula S-1
  • RSi hydrogen or chlorine and Rs 2 is hydrogen, dC 8 -alkyl or Ci-C ⁇ -alkyl substituted by Ci-Ce-alkoxy or C 3 -C 6 -alkenyloxy; or a compound of the formula S-Il
  • egg is nitrogen or methine
  • Rs ⁇ 8 , Rs ⁇ 9 , Rs 20 and Rs 2 ⁇ independently of one another are hydrogen or CC 4 alkyl, or Rs 18 and Rs ⁇ 9 or Rs 2 o and Rs 2 ⁇ together form a C 4 -C 6 alkylene bridge through oxygen , NH or -N (-CC-alkyl) - can be interrupted;
  • C alkyl may be substituted, or Rs i3 and Rs M together form a C 3 -C -
  • Alkenylene bridge which can be substituted by halogen or dC 4 alkyl, or Rs ⁇ 3 and
  • RS 22 , Rs 23 , Rs 24 and Rs 25 independently of one another represent hydrogen, halogen, dC 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -alkylthio, -COORs 26 , trifluoromethyl, nitro or cyano, where Rs 6 are each hydrogen, d-C ⁇ 0 alkyl, dC 4 -alkoxy-C ⁇ -C 4 alkyl, dd-dd-alkylthio-alkyl, di-Ci-d-alkylamino-d-d alkyl, halo-dC 8 alkyl, C 2 -C 8 alkenyl, halo-C 2 -C 8 alkenyl, C 3 -C 8 alkynyl, C 3 -C 7 cycloalkyl, halo-C 3 -C 7 cycloalkyl, -C-C 8 alkylcarbonyl , Allylcarbony
  • Rs ⁇ 7 represents hydrogen or -CC 4 alkyl
  • Rs 27 is hydrogen, halogen, nitro, -CC alkyl or methoxy
  • Rs 28 is hydrogen, halogen, C 1 -C 4 -alkyl, trifluoromethyl, C 1 -C 6 -alkoxy, C 1 -C 6 -alkylthio, - COOH or -COO-C 1 -C 4 -alkyl;
  • Rs 29 is hydrogen, halogen, cyano, nitro, CrC 4 -alkyl, -C-C 4 -haloalkyl, CC 4 -alkylthio, C ⁇ -C 4 -alkylsulfinyl, C, -C 4 -alkylsulfonyl, -COOH, -COO-C ⁇ - C 4 alkyl, -CONRs 30 Rs 3 ⁇ , C (O) - phenyl, or phenyl substituted by halogen, C ⁇ -C alkyl, methoxy, nitro or trifluoromethyl, or -SO 2 NRS 32 RS 3S , -OSO 2 -dC 4 -alkyl, Ci-C ⁇ -alkoxy, or dC 6 -alkoxy substituted by -CC 4 -alkoxy or halogen, or C 3 -C 6 -alkenyloxy or C 3 -C 6 -alkenyloxy substitute
  • Rs 38 is hydrogen, halogen or -CC alkyl
  • Rs 39 is hydrogen, halogen, -CC 4 -alkyl, -COOH, -COO-C C 4 -alkyl, trifluoromethyl or
  • Rs 40 is hydrogen, halogen, nitro, dC 4 alkyl, CC 4 alkoxy, C 1 -C 4 alkylthio, CC 4 -
  • Alkylsulfinyl, CC -Alkylsulfonyl, -COOH, -COO-C ⁇ -C 4 alkyl or CONRs 42 Rs 43 means;
  • Rs 4 is hydrogen, halogen or dC 4 alkyl; or Rs 0 and Rs 4i together form a C 3 -C alkylene bridge;
  • Rs 42 and Rs "independently of one another are hydrogen or dd-alkyl, or Rs 42 and Rs" together form a C 4 -C 6 alkylene bridge which can be replaced by oxygen, NH or -N (d-
  • C 4 alkyl) - can be interrupted
  • RS J is hydrogen, halogen, -CC 4 -alkyl, -COOH, -COO-dC 4 -alkyl, trifluoromethyl or
  • Rs 45 is hydrogen, halogen, nitro, C 1 -C 4 -alkyl, dC 4 alkoxy, C 1 -C 4 alkylthio, C 1 -C 4 -
  • Alkylsulfinyl, CC 4 -alkylsulfonyl, -COOH, -COO-C ⁇ -C 4 alkyl or CONRs 46 Rs 47 means;
  • Rs 46 and Rs 47 independently of one another are hydrogen or dC 4 -alkyl, or Rs ⁇ and Rs 47 together form a C 4 -C 6 -alkylene bridge which can be replaced by oxygen, NH or -N (C
  • C-alkyl) - can be interrupted
  • Alkylsulfinyl, dC 4 -alkylsulfonyl, -COOH, -COO-C ⁇ -C 4 alkyl or CONRs 50 Rs 5 ⁇ means;
  • Rs 51 and Rs 52 independently of one another are hydrogen or C -C 4 alkyl, or Rs 5 ⁇ and Rs 52 together form a C 4 -C 6 alkylene bridge which is replaced by oxygen, NH or -N (d-d-alkyl) - can be interrupted; or a compound of formula SV
  • RS53 and RS 5 4 are independently dC 6 alkyl or C 2 -C 6 alkenyl; or Rs 53 and Rs 55 and Rs 56 independently
  • r represents 0 or 1
  • Rs is hydrogen or C 4 -alkyl, which by C ⁇ -C 4 -alkoxy, C 4 alkylthio, CC 4 - alkylsulfinyl, C ⁇ -C 4 alkylsulfonyl, C ⁇ -C 4 haloalkyl, dC 4 haloalkoxy dd- Haloalkylthio, dC -haloalkylsulfinyl, dC 4 -haloalkylsulfonyl, nitro, cyano, - COOH, COO-dC 4 -alkyl, -NRs 80 Rs 8 ⁇ , -SO 2 NRs 82 Rs 83 or -CONRs ⁇ -tRs ⁇ s;
  • Rs 78 is hydrogen, halogen, dC 4 alkyl, trifluoromethyl, dC 4 alkoxy or dd haloalkoxy;
  • Rs 79 is hydrogen, halogen or -CC 4 alkyl
  • Rs 80 is hydrogen, -CC alkyl or -CC 4 alkylcarbonyl
  • Rs 8 is hydrogen or C 1 -C 4 alkyl
  • Rs 80 and Rs 8 ⁇ together form a C 4 or C 5 alkylene group
  • Rs 82 , Rs ⁇ , Rs ⁇ A and Rs ⁇ independently of one another are hydrogen or C 1 -C 4 -alkyl; or Rs 82 together with Rs ⁇ or Rs ⁇ together with Rs 85 independently of one another are C 4 - or C -alkylene, where one carbon atom is oxygen or sulfur, or one or two carbon atoms is -NH- or -N (dC 4 -alkyl ) - can be replaced;
  • Rs 86 and Rs 87 are independently hydrogen or Ci-C ⁇ -alkyl; or Rs 86 and Rs 87 together are C 2 -C 6 alkylene;
  • Rs 88 and Rs 89 independently of one another are hydrogen or -CC 8 alkyl; or Rs 88 and Rs 89 together form a C 2 -C 6 alkylene group;
  • RS 90 stands for Rs 9 ⁇ -O-, Rs 92 -S- or -NRs 93 Rs 94 ;
  • Rs 9 ⁇ and Rs 92 independently of one another hydrogen, C ⁇ -C 8 alkyl, Ci-Ce-haloalkyl, d- C 4 alkoxy-C 1 -C 8 alkyl, C 3 -C 6 alkenyloxy-dC 8 alkyl or phenyl-C C 8 -alkyl, where the phenyl ring can be substituted by halogen, dd-alkyl, trifluoromethyl, methoxy, methylthio, methylsulfinyl or methylsulfonyl, or C 3 -C 6 -alkenyl, C 3 -C 6 -halogenalkenyl, phenyl Are -C 3 -C 6 alkenyl, C 3 -C 6 alkynyl, phenyl-C 3 -C 6 alkynyl, oxetanyl, furyl or tetrahydrofuryl;
  • Rs 95 and Rs 96 independently of one another are hydrogen or -CC 8 alkyl; or Rs 95 and Rs 96 together form a C 2 -C 6 alkylene group; and Rs 97 is C 2 -C 4 alkenyl or C 2 -C 4 alkynyl; with the provisos that a) at least one of the ring members E 2 , E 3 , E 4 or E 5 is carbonyl, and a ring member adjacent to this or these ring members is the group
  • Rs 98 is hydrogen, -CC 6 alkyl, C 3 -C 6 cycloalkyl, C 3 -C 6 alkenyl or C 3 -C 6 alkynyl; and Rs 99 , Rsioo and RS 101 independently of one another denote hydrogen, d-C ⁇ -alkyl, C 3 -C 6 cycloalkyl or CC 6 alkoxy, with the proviso that one of the substituents Rs 99 , Rsioo and RS 101 is different from hydrogen is; or a compound of formula SX
  • E 6 is nitrogen or methine
  • n for the case that E 6 is nitrogen, 0, 1, 2 or 3 and for the case that E 6 is methine, 0, 1, 2, 3 or 4,
  • RS 102 halogen , C ⁇ -C 4 -alkyl, C haloalkyl, C ⁇ -C 4 -alkoxy, C 4 haloalkoxy, nitro, -C 4 alkylthio, dd- alkylsulfonyl, C ⁇ -C 4 alkoxycarbonyl, phenyl or phenoxy, or C ⁇ -C 3 -alkyl, C 3 - haloalkyl, C ⁇ -C 3 -alkoxy, represents C 3 haloalkoxy, halogen, cyano or nitro-substituted phenyl or phenoxy;
  • Rs ⁇ 03 hydrogen or -CC 4 alkyl;
  • E 7 is oxygen or N-Rsios and Rs i05 a group of the formula
  • E 8 is oxygen, sulfur, sulfinyl, sulfonyl or methine, Rsio ⁇ and Rs ⁇ 09 independently of one another CH 2 COORsn 2 or COORsn 3 or together a group of the formula - (CH 2 ) C (O) -OC (O) - (CH 2 ) - mean, and Rsn 2 and Rsn 3 independently of one another hydrogen, dd-alkyl, C 2 -C 4 alkenyl, C 2 -C 6 alkynyl, C 3 -C 6 - cycloalkyl, C ⁇ -C haloalkyl Mean metal or an ammonium cation; and Rsno and Rsm independently of one another are hydrogen, halogen or -CC 4 alkyl; or a compound of the formula S-Xlll
  • Rs and Rsn 5 independently of one another are hydrogen, halogen or dd-haloalkyl
  • Rsne is hydrogen, C, -C -alkyl, C 3 -C -alkenyl, C 3 -C -alkynyl, dC 4 - haloalkyl, C 3 -C 6 Cycloalkyl, a metal cation or an ammonium cation
  • Rs 118 , Rsn 9 , Rs 121 and Rs 122 independently represent hydrogen or dd-alkyl;
  • Rs 117 and Rs ⁇ 20 independently of one another hydrogen, dd-alkyl, C 3 -C 4 alkenyl, C 3 -C 4 alkynyl, CrC 4 haloalkyl, C 3 -C 6 cycloalkyl, a metal cation or an ammonium cation mean; or a compound of formula S-XIV
  • Rs ⁇ 23 is hydrogen, cyano, halogen, C 1 -C 4 alkyl, C 3 -C 6 cycloalkyl, C 1 -C alkoxy, d-
  • RS 125 and RS 126 independently of one another dC-alkyl, CC 4 -haloalkyl, C 3 -C 4 -alkenyl,
  • Heteroaryl or by -CC 3 alkyl, CC 3 haloalkyl, CC 3 alkoxy, C -C 3 haloalkoxy,
  • Rs ⁇ 27 and Rs ⁇ 28 independently of one another hydrogen, C ⁇ -C 4 alkyl, C ⁇ -C - haloalkyl, CC 4 -alkoxy, mono-C ⁇ -C 8 - or di-C1-C8-alkylamino, C 3 -C 6 - Mean cycloalkyl, d-C -thioalkyl, phenyl or heteroaryl;
  • Rs 129 are hydrogen, C 4 -alkyl, C 4 haloalkyl, C r C 4 alkoxy, mono-C C 8 - or di-C1-C8-alkylamino, C 3 -C 6 cycloalkyl, dC 4 -Thioalkyl, phenyl, heteroaryl, OH, NH 2 , halogen, di -CC-C 4 -aminoalkyl, -C-C 4 -alkylthio, dC 4 -alkylsulfonyl or dC -alkoxycarbonyl;
  • Rs 130 is hydrogen, dd-alkyl, C ⁇ -C 4 haloalkyl, C r C alkoxy, C ⁇ -C 8 mono - or di-C1-C8-alkylamino, C 3 -C 6 cycloalkyl, C ⁇ -C 4 - Thioalkyl, phenyl, heteroaryl, cyan
  • Rs ⁇ 32 is hydrogen, C -alkyl, CC 4 -haloalkyl, C 2 -C 4 -alkenyl, C 2 -C 4 -alkynyl or d- C 4 -alkoxy-C r C 4 -alkyl;
  • Rs ⁇ is hydrogen, halogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl or C 1 -C 4 alkoxy and Rs ⁇ hydrogen, halogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl or CC 4 alkoxy; with the proviso that Rsi ⁇ and Rs ⁇ do not simultaneously represent hydrogen.
  • Safeners which are particularly preferred for the agent according to the invention are selected from the group of compounds of the formula S1.1
  • the compounds of the formulas S1.1 to S1.13 are known and are described, for example, in the Pesticide Manual, eleventh ed., British Crop Protection Council, 1997 under entry numbers 61 (formula S1.1, Benoxacor), 304 (formula S1.2 , Fenclorim), 154 (Formula S1.3, Cloquintocet), 462 (Formula S1.4, Mefenpyr-diethyl), 377 (Formula S1.5, Furilazole), 363 (Formula S1.8, Fluxofenim), 213 (Formula S1 .9, dichlormid) and 350 (formula S1.10, flurazole).
  • the compound of formula S1.11 is known under the name MON 4660 (Monsanto) and e.g. in EP-A-0 436 483.
  • the compound of formula S1.6 (AC 304415) is described for example in EP-A-0 613 618, the compound of formula S1.7 in DE-A-2948535.
  • the compound of the formula S1.12 is described in DE-A-4331448, the compound of the formula S1.13 in DE-A-3525205.
  • reaction mixture was degassed by introducing Agron for 0.33 h. Then was
  • Tetrakistriphenylphosphine-Pd (0) (1.46g, 1.28 mmol) was added.
  • reaction mixture was heated to 100 ° C. for 16 h, cooled and washed with NaOH solution (1N,
  • TMEDA (17.1g, 0.147 mol) was dissolved in THF (distilled over Na, 500 ml), cooled to -78 ° C. and mixed with s-BuLi (113 ml of a 1.3M solution in cyclohexane, 0.147 mol). The reaction mixture was stirred at -78 ° C for 0.25 h, a solution of 13 (33.9 g, 0.134 mol) in THF (100 ml) was added dropwise and the mixture was stirred at -78 ° C for a further 0.25 h. The reaction mixture was treated dropwise with iodoethane (45.2g, 0.29 mol) and warmed to 0 ° C.
  • TMEDA (8.9g, 0.077 mol) was dissolved in THF (distilled over Na, 400 ml), the reaction mixture was cooled to -78 ° C. and with s-BuLi (59 ml of a 1.3M solution in cyclohexane, 0.077 mol) and then a solution of 23 (24.8g, 0.07 mol) in THF (75 ml) was added dropwise. After 0.5 h at -78 ° C, the reaction mixture was mixed with iodomethane (13.3g, 0.085 mol) and warmed to 0 ° C. Aqueous, saturated NHCl solution (200 ml) was added to the reaction mixture and the organic phase was separated off.
  • TMEDA (15.1g, 0.13 mol) was dissolved in THF (500 ml), cooled to -78 ° C. and s-BuLi (100 ml of a 1.3 M solution in cyclohexane, 0.13 mol) was added dropwise. 13 (30 g, 0.12 mol) was dissolved in THF (100 ml) and added dropwise to the reaction mixture within 0.5 h. After a further 0.5 h at -78 ° C, the reaction mixture was mixed with trimethyl borate. The reaction mixture was stirred at -78 ° C for 0.5 h, warmed to -40 ° C and mixed with an aqueous NH 4 CI solution (250 ml). The organic phase was washed with brine, dried over Na 2 SO4 and concentrated. 32 (36.7 g) was obtained as a crude product.
  • TMEDA (1.49 g, 12.8 mmol) was dissolved in THF (50 ml) and cooled to -78 ° C.
  • the reaction mixture was mixed with s-BuLi (9.8 ml of a 1.3 M solution in cyclohexane, 12.8 mmol), stirred for 0.25 h at -78 ° C., with a solution of 34 (3.3 g, 11.6 mmol) in THF (15 ml) dropwise added and stirred at -78 ° C for 0.3h.
  • Ethyl iodide (2.0g, 13 mmol) was added to the reaction mixture.
  • the reaction mixture was warmed to 0 ° C.
  • N, N'-diacethylhydrazine 14 (768 g, 6.62 mol), 2,2'-dichlorodiethyl ether (1141 g, 7.9 mol) and potassium carbonate (1827 g, 13.3 mol) were initially charged in DMF (8.5 L) at room temperature.
  • the resulting suspension was heated to 130 ° C for 3.5 h, cooled, filtered and concentrated.
  • the residue was taken up in toluene (1000 ml) and stirred at 0 ° C for 16 h. After filtration, the product 15 was obtained as white crystals (574 g).
  • the mother liquor was evaporated and recrystallized from a little methanol.
  • Product 15 (108 g) was again obtained as white crystals.
  • LC / MS: M + means the molecular weight determined from the coupled HPLC (High Performance Liquid Chromatography) and MS (Mass Spectrometry) analysis; the numerical values given after "UV” mean the frequency of the absorption maxima of the UV spectrum in nanometers, measured in water / acetonitrile.
  • Ph phenyl
  • Ph phenyl
  • Ph phenyl
  • Ph phenyl
  • Ph phenyl
  • Ph phenyl
  • Ph phenyl
  • test plants Monocot and dicot test plants are sown in pots in standard soil.
  • the test substances are used as an aqueous suspension (made from a wettable powder (example F3, b) according to WO 97/34485) or as an emulsion (made from an emulsion concentrate (example F1, c) according to WO 97 / 34485) sprayed on in optimal dosage (500 l water / ha).
  • the test plants are then cultivated further in the greenhouse under optimal conditions.

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PCT/EP2000/008657 1999-09-07 2000-09-05 Neue herbizide WO2001017973A2 (de)

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PL00356456A PL356456A1 (en) 1999-09-07 2000-09-05 Novel herbicides
AU75146/00A AU7514600A (en) 1999-09-07 2000-09-05 Novel herbicides
EP00964108A EP1230245A2 (de) 1999-09-07 2000-09-05 Neue herbizide
HU0202844A HUP0202844A3 (en) 1999-09-07 2000-09-05 Herbicidal 4-phenyl substituted pirazolinone derivatives, intermediates and preparation thereof
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WO2003062244A1 (en) * 2002-01-22 2003-07-31 Syngenta Participations Ag Phenyl substituted heterocyclic compounds useful as herbicides
WO2004111042A1 (de) * 2003-06-12 2004-12-23 Bayer Cropscience Aktiengesellschaft N-heterocyclyl-phenylsubstituierte cyclische ketoenole
WO2005016933A1 (de) * 2003-08-14 2005-02-24 Bayer Cropscience Aktiengesellschaft 4-biphenylsubstituierte-4-substituierte-pyrazolidin-3,5-dione als schädlingsbekämpfungsmittel und/oder mikrobiozide und/oder herbizide
WO2005016873A3 (de) * 2003-08-14 2005-04-07 Bayer Cropscience Ag 4-biphenylsubstituierte pyrazolidin-3,5-dion- derivative als schädlingsbekämpfungsmittel und/oder herbizide und/oder mikrobiozide
WO2006045587A1 (en) * 2004-10-27 2006-05-04 Syngenta Participations Ag A process for the preparation of [1,4,5]-oxadiazepine derivatives
WO2007096058A1 (de) 2006-02-21 2007-08-30 Bayer Cropscience Ag Cycloalkyl-phenylsubstituierte cyclische ketoenole
US7420062B2 (en) 2003-07-14 2008-09-02 Bayer Cropscience, Ag Hetaryl-substituted pyrazolidindione derivatives with pesticidal characteristics
WO2010102758A2 (de) 2009-03-11 2010-09-16 Bayer Cropscience Ag Halogenalkylmethylenoxy-phenyl-substituierte ketoenole
JP2011506369A (ja) * 2007-12-13 2011-03-03 シンジェンタ リミテッド 除草剤としての４−フェニルピラン−３，５−ジオン類、４−フェニルチオピラン−３，５−ジオン類、及び２−フェニルシクロヘキサン−１，３，５−トリオン類
WO2011098433A1 (de) 2010-02-15 2011-08-18 Bayer Schering Pharma Aktiengesellschaft Zyklische ketoenole zur therapie
WO2012091156A1 (en) 2010-12-27 2012-07-05 Sumitomo Chemical Company, Limited Pyridazinone compound and herbicide and noxious arthropod controlling agent comprising it
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WO2001017973A3 (de) 2001-05-10
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