EP1697321A1 - Derives d'acide tetramique spirocycliques substitues par 2-halogeno-6-alkylphenyle - Google Patents

Derives d'acide tetramique spirocycliques substitues par 2-halogeno-6-alkylphenyle

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Publication number
EP1697321A1
EP1697321A1 EP04797575A EP04797575A EP1697321A1 EP 1697321 A1 EP1697321 A1 EP 1697321A1 EP 04797575 A EP04797575 A EP 04797575A EP 04797575 A EP04797575 A EP 04797575A EP 1697321 A1 EP1697321 A1 EP 1697321A1
Authority
EP
European Patent Office
Prior art keywords
alkyl
alkoxy
optionally
formula
compounds
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Withdrawn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
EP04797575A
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German (de)
English (en)
Inventor
Stefan Lehr
Mark Wilhelm Drewes
Dieter Feucht
Peter Lösel
Olga Malsam
Guido Bojack
Christian Arnold
Thomas Auler
Martin Jeffrey Hills
Heinz Kehne
Christopher Hugh Rosinger
Reiner Fischer
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Bayer CropScience AG
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Bayer CropScience AG
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Publication date
Application filed by Bayer CropScience AG filed Critical Bayer CropScience AG
Publication of EP1697321A1 publication Critical patent/EP1697321A1/fr
Withdrawn legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/54—Spiro-condensed
    • 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
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/36—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom five-membered rings
    • 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
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/36—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom five-membered rings
    • A01N43/38—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom five-membered rings condensed with carbocyclic rings
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
    • C07D309/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
    • C07D309/08—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no 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
    • C07D309/14—Nitrogen atoms not forming part of a nitro radical
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
    • C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
    • C07D491/10—Spiro-condensed systems

Definitions

  • the invention relates to new .2-halo-6-alkyl7phenyl-substituted spirocychic tetramic acid derivatives, several processes and intermediates for their preparation and their use as pesticide and / or herbicides.
  • the invention also relates to new selective herbicidal combinations of active ingredients, the 2-halogen-6-alkyl-phenyl-substituted spirocychic tetram. acid derivatives on the one hand and at least one • the. Cultivated crop compatibility, on the other hand, contain an improved compound and can be used with particularly good success for selective weed control with various crop plants.
  • EP-A-0262 399 and GB-A-2 266 888 disclose similarly structured compounds (3-aryl-pyrrolidin-2,4-diones), of which no herbicidal, insecticidal or acaricidal activity has been disclosed.
  • Unsubstituted, bicyclic 3-aryl-pyrrohdin-2,4-dione derivatives EP-A-355 599 and EP-A-415 211) and substituted monocyclic 3-aryl-pyrrolidin-2 are known to have herbicidal, insecticidal or acaricidal activity , 4-dio derivatives (EP-A-377 893 and EP-A-42077).
  • EP-A-442 073 polycyclic 3-arylpyrrolidine-2,4-dione derivatives
  • EP-A-442 073 polycyclic 3-arylpyrrolidine-2,4-dione derivatives
  • EP-A-456063 EP-A-521 334, EP-A-596298 , EP-A-613 884, EP-A-613 885 WO 94/01 997, WO 95/26954, WO 95/20 572, EP-A 0 668 267, WO 96/25 395, WO 9635 664, WO 97 / 01 535, WO 97/02243, WO 97/36 868, WO 97/43275, WO / 98/05638, WO 98/06721 ,.
  • Y represents alkyl
  • Z represents C 2 -C 6 alkyl
  • a and B together with the carbon atom to which they are attached represent a saturated or unsaturated C3-Cg ring which may contain at least one heteroatom and which is optionally substituted by alkoxy or haloalkyl,
  • E represents a metal ion equivalent or an ammonium ion
  • L represents oxygen or sulfur
  • M oxygen or sulfur
  • R 1 for each optionally substituted alkyl, alkenyl, alkoxyalkyl, alkylthioalkyl or polyalkoxyalkyl or for each optionally substituted by halogen, alkyl or alkoxy ated cycloalkyl or heterocyclyl or for each optionally substituted phenyl, phenylalkyl, phenylalkenyl or.
  • Hetaryl stands
  • R 2 for each optionally substituted by halogen alkyl, alkenyl ,.
  • R 3 , R 4 and R 5 independently of one another each for alkyl, alkoxy, alkylamino, dialkylamino, alkylthio, alkenylthio or cycloalkylthio optionally substituted by halogen or for. each optionally substituted phenyl, benzyl, phenoxy or phenylthio,
  • R 6 and R 7 independently of one another represent hydrogen, in each case optionally substituted by halogen ' alkyl, cycloalkyl, alkenyl, alkoxy, alkoxyalkyl, in each case optionally substituted phenyl or benzyl, or together with the N atom to which they are attached, form an optionally substituted cycle optionally containing oxygen or sulfur. , ,
  • the compounds of formula (I) can, also depending on the nature of the substituents. geometric and / or optical isomers or mixtures of isomers, in different compositions, which can optionally be separated in a conventional manner. Both the pure isomers and the isomer mixtures, their preparation and use, and agents containing them are the subject of the present invention. For the sake of simplicity, the following always refers to compounds of the formula (!), although both the pure compounds and, if appropriate, mixtures with different proportions of isomeric compounds are meant.
  • A, B, E, L, M, X, Y, Z, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 and R 7 have the meanings given above.
  • A, B, X, Y and Z have the meanings given above if
  • A, B, X, Y and Z have the meanings given above, and
  • R 8 represents alkyl (preferably C r C 6 alkyl), intramolecularly condensed in the presence of a diluent and in the presence of a base.
  • (B) Ma receives compounds of the formula (Ib) shown above, in which A, B, R 1 , X, Y and Z have the meanings given above, if compounds of the formula (Ia) shown above, in which A, B , X, Y and Z have the meanings given above,
  • R 1 has the meaning given above and
  • R 1 the above. Has meaning, if appropriate in the presence of a diluent and, if appropriate, in the presence of an acid binder.
  • R 2 and M have the meanings given above, if appropriate in the presence of a diluent and if appropriate in the presence of an acid binder.
  • M and R 2 have the meanings given above, if appropriate in the presence of a diluent and if appropriate in the presence of an acid binder or
  • Hai represents chlorine, bromine or iodine, if appropriate in the presence of a diluent and if appropriate in the presence of a base.
  • R 4 and R 5 have the meanings given above and
  • Hai represents halogen (especially chlorine or bromine), if appropriate in the presence of a diluent and if appropriate in the presence of an acid binder.
  • Me represents a mono- or divalent metal (preferably an alkali metal or alkaline earth metal such as lithium, sodium, potassium, magnesium. Or calcium), t represents the number 1 or 2 and
  • R 10 , R n , R 12 independently of one another represent hydrogen or alkyl (preferably C 1 -C 6 -alkyl), optionally reacted in the presence of a diluent.
  • R 6 and L have the meanings given above, if appropriate in the presence of a diluent and if appropriate in the presence of a catalyst or
  • L, R 6 and R 7 have the meanings given above, if appropriate in the presence of a diluent and if appropriate in the presence of an acid binder.
  • the new compounds of the formula (I) have very good activity as pesticides, preferably as insecticides and / or acaricides and / or as herbicides.
  • Methyl-phenyl) -urea Daimuron, Dymron
  • 3,6-dichloro-2-methoxy-benzoic acid Dicamba
  • Piperidine-1-thiocarboxylic acid-Sl-methyl-1-phenyl-ethyl ester (dimepiperate), 2,2-dichloro-N- (2-oxo-2- (2-propenylamino) -ethyl) rN- (2-propenyl) - acetamide (DKA-24), 2,2-dichloro-N, N-di-2-propenyl-acetamide (dichlormid), 4,6-dichloro-2-phenylpyrimidine (fenclorim), l- (2, 4-dichlorophenyl) -5-trichloromethyl-1H-l, 2,4-triazole-3-carboxylic acid ethyl ester (fenchlorazole-ethyl - see also related compounds in EP-A
  • n a number 0, 1, 2, 3, 4 or 5
  • a 1 represents one of the divalent heterocyclic groupings outlined below,
  • n is a number 0, 1, 2, 3, 4 or 5
  • a 2 represents alkanediyl with 1 or 2 carbon atoms which is optionally substituted by CC 4 alkyl and / or C 1 -C 4 alkoxy-carbonyl and / or C 1 -C 4 alkenyloxy carbonyl
  • R 14 represents hydroxyl, mercapto, amino, -C 6 -alkoxy, C 6 -C 6 -alkylthio, C r C 6 -alkylamino or di- (CC 4 -alkyl) -amino
  • R 15 for hydroxy, mercapto, amino, CC 7 -alkoxy, -C-C 6 -alkylthio, Q- -alkenyloxy, rC ⁇ - alkenyl ⁇ xy- -C ⁇ -C 6 -alkoxy, C r C 6 -alkylamino or di- (-C ⁇ -C 4 -alkyl) -amino,
  • R 16 represents CC 4 alkyl which is optionally substituted by fluorine, chlorine and / or bromine,
  • R 17 for hydrogen, in each case optionally substituted by fluorine, chlorine and / or bromine, C Ce alkyl, C 2 -C 6 alkenyl or C 2 -C 6 alkynyl, -C-C 4 alkoxy-C r C 4 alkyl , Dioxolanyl-Ci-G, -. alkyl, furyl, furyl -CC-alkyl, thienyl, thiazolyl, piperidinyl, or phenyl which is optionally substituted by fluorine, chlorine and / or bromine or C 1 -C 8 -alkyl,
  • R 18 for hydrogen, in each case optionally substituted by fluorine, chlorine and / or bromine .
  • R 19 represents hydrogen, cyano, halogen, or CrG t -alkyl, C 3 -C 6 -cycloalkyl or phenyl which are optionally substituted by fluorine, chlorine and / or bromine,
  • R 20 represents hydrogen, optionally substituted by hydroxy, cyano, halogen or C 1 -C 4 -alkoxy-substituted C, -C 6 -alkyl, C 3 -C 6 -cycloalkyl or tri- (C r C 4 -alkyl) -silyl,
  • R 21 represents hydrogen, cyano, halogen, or Q-Gralkyl, C 3 -C 6 -cycloalkyl or phenyl which are each optionally substituted by fluorine, chlorine and / or bromine,
  • X 1 represents nitro, cyano, halogen, C r C 4 alkyl, CC 4 haloalkyl, C 1 -C 4 alkoxy or CC 4 - haloalkoxy,
  • X 2 represents hydrogen, cyano, nitro, halogen, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, Q-Gj-alkoxy or C ⁇ - C 4 -haloalkoxy, X 3 . 4 -alkoxy or C ⁇ -C 4 haloalkoxy is hydrogen, cyano, nitro, halogen, Q-GrAlkyl, QQ-haloalkyl, QC,
  • Rr represents hydrogen or C r C 4 alkyl
  • Rr represents hydrogen or Q- alkyl
  • R 24 for hydrogen, in each case optionally substituted by cyano, halogen or Ci-Q-alkoxy-substituted CrQ-alkyl, CC 6 -alkoxy, -C-C 6 -alkylthio, CC 6 -alkylamino or di- (CC 4 -alkyl) - amino, or in each case optionally substituted by cyano, halogen or -CC 4 alkyl-substituted C 3 -C 6 cycloalkyl, C 3 -C 6 cycloalkyloxy, C 3 -C 6 cycloalkylthio or C 3 -C 6 cycloalkylamino,
  • R represents hydrogen, optionally substituted by cyano, hydroxy, halogen or CC 4 alkoxy -CC 6 alkyl, in each case optionally substituted by cyano or halogen-substituted C 3 -C 6 - Alkenyl or C 3 -C 6 -Alkmyl, or optionally cyano-, halogen or Q-Gj-alkyl substituted C 3 -C 6 cycloalkyl,
  • R 26 represents hydrogen, optionally cyano-, hydroxyl-, halogen or C ⁇ -C 4 alkoxy-substituted Ci-C ⁇ -alkyl, in each case optionally cyano- or halogen-substituted C 3 -C 6 - alkenyl or C 3 -C 6 alkynyl optionally by cyano, halo or C ⁇ -C 4 -alkyl-substituted C 3 -C 6 cycloalkyl, or gegeberienorganizls by nitro, cyano, halogen, CC 4 -alkyl, C 4 haloalkyl, C ⁇ -C4-alkoxy, or Q GrHalogenalkoxy substituted phenyl, or together with R 25 is optionally substituted by C ⁇ -C respectively 4 alkyl-substituted C 2 -C ⁇ - alkanediyl or C 2 -C 5 -oxaalkanediyl,
  • X 4 represents nitro, cyano, carboxy, carbamoyl, formyl, sulfamoyl, hydroxy, amino, halogen, CC 4 -alkyl, C 4 haloalkyl, CC 4 -alkoxy or C ⁇ -C is 4 haloalkoxy, and
  • X 5 represents nitro, cyano, carboxy, carbamoyl, formyl, sulfamoyl, hydroxy, amino, halogen, CC-alkyl 5 -C-C 4 -haloalkyl, -C-C 4 -alkoxy or CC 4 -haloalkoxy.
  • X preferably represents chlorine or bromine
  • Y preferably represents -C 3 alkyl
  • Z preferably represents ethyl, n-propyl or n-butyl
  • A, B and the carbon atom to which they are attached preferably represent saturated C 3 -C 8 cycloalkyl, in which a methylene group is optionally replaced by oxygen or sulfur and which is optionally substituted by Ci-Q-haloalkyl or Ci-Ce-alkoxy is
  • G preferably represents hydrogen (a) or one of the groups
  • E represents a metal ion equivalent or an ammonium ion
  • L represents oxygen or sulfur
  • M oxygen or sulfur
  • R 1 preferably represents in each case optionally one to seven times by halogen, one to two times by cyano, simply by COR 13 , substituted C r C 20 alkyl, C 2 -C 20 alkenyl, -C-C 6 -alkoxy-C, -C 6 -alkyl, C r C 6 -alkylthio-C C 6 -alkyl or poly-C ⁇ -C 4th -Alkoxy-C ⁇ -C 4 -alkyl or for C 3 -C 8 -cycloalkyl which is optionally monosubstituted to trisubstituted by halogen, C r C 4 -alkyl or Cj-C 4 -alkoxy, in which optionally one or two not directly ' adjacent Methylene groups are replaced by oxygen and / or sulfur, each optionally up to three times by halogen, cyano, nitro, C 1 -C 6 -alkyl, Q-C 6 -alkoxy, C
  • R 2 preferably represents in each case optionally mono- to trisubstituted by halogen-substituted CC 2 o-alkyl, C 2 -C 20 alkenyl, dC 6 alkoxy-C 2 -C 6 alkyl or poly-C, -C 6 alkoxy- C 2 -C 6 alkyl, for C 3 -C 3 cycloalkyl optionally substituted once to twice by halogen, CC 6 alkyl or C 1 -C 6 alkoxy or for each optionally monosubstituted to triple by halogen, cyano, nitro, CC 6 alkyl, Cj-C ⁇ alkoxy, C ⁇ -C 6 haloalkyl or C ⁇ -C 6 haloalkoxy-substituted phenyl or benzyl,
  • R 3 preferably represents C 1 -C 6 -alkyl which is optionally mono- to polysubstituted by halogen or represents in each case optionally monosubstituted to double by halogen, -C 6 -alkyl, C r C 6 -alkoxy, Ci-Q-haloalkyl, -CC 4 -haloalkoxy, cyano or nitro substituted phenyl or benzyl, '
  • R 4 and R 5 independently of one another preferably each represent optionally mono- to trisubstituted by halogen Q-Cg-alkyl, -C-C 8 alkoxy, CC 8 -alkylamino, di- (-C-C 8 -alkyl) amino, CC 8 -Alkylthio or C 2 -C 8 -alkenylthio or for each optionally single to triple by halogen, nitro, cyano, CC 4 -alkoxy, QQ-haloalkoxy, -C-C 4 -alkylthio, -C-C 4 -haloalkylthio, -C-C 4 alkyl or C ⁇ -C 4 -halogenoalkyl-substituted phenyl, phenoxy or phenylthio,
  • R 6 and R 7 independently of one another preferably represent hydrogen, represent in each case optionally mono- to trisubstituted by halogen, Cj-C 8 alkyl, C 3 -C 8 cycloalkyl, Q-Cg alkoxy, C 3 -C 8 -alkenyl or C 1 -C 8 -alkoxy-C 2 -C 8 -alkyl, for each optionally optionally up to triple by halogen, C] -C 8 -alkyl, CC 8 -haloalkyl or CC 8 -alkoxy-substituted phenyl or benzyl or together for one optionally mono- or disubstituted by C ⁇ -C 4 alkyl-substituted C 3 -C 6 -alkylene radical in which optionally one methylene group is replaced by oxygen or sulfur,
  • R 13 preferably represents in each case optionally mono- to trisubstituted by halogen-substituted C r C 6 alkyl, C 3 -C 6 alkenyl, C 3 -C 6 -alkynyl or C ⁇ -C 4 -alkoxy-C 2 -C 4 alkyl or for Q-Cg-cycloalkyl which is optionally mono- to disubstituted twice by halogen, QQ-alkyl or -CC 2 -alkoxy, in which one or two non-directly adjacent methylene groups are optionally replaced by oxygen or, if appropriate in each case once or twice, by halogen , Ci-GrAlkyl, -CC 4 alkoxy, -C-C 2 haloalkyl, Q-.
  • R * 3 '- preferably represents hydrogen, C] -C 6 alkyl or C 3 -C 6 alkenyl.
  • halogen represents fluorine, chlorine, bromine and iodine, in particular fluorine, chlorine and bromine.
  • X particularly preferably represents chlorine or bromine
  • Y particularly preferably represents methyl or ethyl
  • Z particularly preferably represents ethyl or n-propyl
  • A, B and the carbon atom to which they are attached are particularly preferably saturated C 3 -C 7 -cycloalkyl, where optionally a methylene group by oxygen is replaced and which is optionally simply substituted by QQ-haloalkyl or -CC 4 alkoxy • ,
  • G particularly preferably represents hydrogen (a) or one of the groups
  • E represents a metal ion equivalent or an ammonium ion
  • L represents oxygen or sulfur
  • M oxygen or sulfur
  • R 2 particularly preferably represents in each case monosubstituted to trisubstituted by fluorine or chlorine -CC- 0 alkyl, C 2 -C 0 -alkenyl, dQ-alkoxy-dQ-alkyl or poly-D-C -alkoxy-C 2 -C 4 alkyl, for C 3 -C 7 cycloalkyl, which is optionally substituted simply by CC 2 alkyl or C 1 -C 2 alkoxy, or for phenyl or benzyl which is optionally mono- to disubstituted by fluorine, chlorine, bromine, cyano, nitro, C 1 -C 4 -alkyl, methoxy, trifluoromethyl or trifluoromethoxy,
  • R 3 particularly preferably represents C 1 -C 4 -alkyl which is optionally monosubstituted to trisubstituted by fluorine or chlorine or each optionally monosubstituted by fluorine, chlorine, bromine, C 1 -d-alkyl, dQ-alkoxy, trifluoromethyl, trifluoromethoxy, cyano or nitro substituted phenyl or benzyl,
  • R 4 and R 5 independently of one another particularly preferably represent in each case optionally mono- to trisubstituted by fluorine or chlorine-substituted d-QrAlkyl, dC 6 alkoxy, C r C 6 - Alkylammo, di- (CC 6 alkyl) arnino, C ⁇ -C 6 -Alkylthio or C 3 -C 4 -alkenylthio or for each optionally optionally up to twice by fluorine, chlorine, bromine, nitro, cyano, CC 3 -alkoxy, trifluoromethoxy, -CC 3 -alkylthio, -C-C 3 alkyl or Trifluoromethyl substituted phenyl, phenoxy or phenylthio,
  • R 6 and R 7 independently of one another particularly preferably represent hydrogen, in each case optionally dC 6 alkyl which is monosubstituted to trisubstituted by fluorine or chlorine, C 3 -C 6 cycloalkyl, CC 4 alkoxy, C 3 -C 6 alkenyl or Ci-C ⁇ -alkoxy-d-qralkyl, for phenyl which is optionally mono- to disubstituted by fluorine, chlorine, bromine, trifluoromethyl, C 1 -C 4 -alkyl or dC 4 -alkoxy, or together for an optionally monosubstituted or disubstituted methyl C ⁇ -alkylene radical, in which a methylene group is optionally replaced by oxygen,
  • R 13 particularly preferably represents Ci-Gi-alkyl, dd-alkene, dC 4 -alkynyl or dd-alkoxy-C 2 -C 3 -alkyl or dQ-cycloalkyl, in which a methylene group is optionally through. Oxygen is replaced.
  • halogen represents fluorine, chlorine and bromine, in particular fluorine and chlorine.
  • X very particularly preferably represents chlorine or bromine,
  • Y very particularly preferably represents methyl
  • Z very particularly preferably represents ethyl
  • A, B and the carbon atom to which they are attached very particularly preferably represent saturated Cg-cycloalkyl, in which a methylene group may be replaced by oxygen and which may be simply by trifluoromethyl, methoxy, ethoxy, n-propoxy ,. iso-propoxy, n-butoxy or iso-butoxy is substituted,
  • G very particularly preferably represents hydrogen (a) or one of the groups
  • L stands for oxygen and M stands for oxygen or sulfur
  • R 1 very particularly preferably represents in each case optionally mono- to trisubstituted by fluorine or chlorine, C r C 6 alkyl, C 2 -C 6 alkenyl, C ⁇ -C 2 alkoxy-C ⁇ -C 2 alkyl, CC 2 - alkylthio -C 1 -C 2 -alkyl or poly-C 1 -C 2 -alkoxy-C 1 -C 2 -alkyl or for each cyclopropyl, cyclopentyl or cyclohexyl which is optionally simply substituted by fluorine, chlorine, methyl, ethyl or methoxy, for optionally simply by fluorine , Chlorine, bromine, cyano, nitro, methyl, ethyl, n-propyl, i-propyl, methoxy, ethoxy, methylthio, ethylthio, methylsulfinyl, ethylsulfiny
  • R 2 very particularly preferably represents -C 8 -alkyl, C 2 -C 6 -alkenyl or dC 3 -alkoxy-C 2 -C 3 -alkyl, cyclopentyl or cyclohexyl, or for each optionally simply by fluorine, chlorine, bromine , Cyano, nitro, methyl, methoxy, trifluoromethyl or trifluoromethoxy substituted phenyl or benzyl,
  • R 3 very particularly preferably represents CC 4 -alkyl which is optionally monosubstituted to trisubstituted by fluorine or chlorine or in each case optionally substituted by fluorine, chlorine, bromine, CC 4 -alkyl, CC 4 -alkoxy, trifluoromethyl, trifluoromethoxy, cyano or nitro Phenyl or benzyl,
  • R 6 very particularly preferably represents hydrogen, C 1 -C 4 -alkyl, C 3 -C 6 -cycloalkyl or allyl, phenyl which is optionally simply substituted by fluorine, chlorine, bromine, methyl, methoxy or trifluoromethyl
  • 7 R represents very particularly preferably for methyl, ethyl, n-propyl, isopropyl or allyl, , 6 ' 7. , , ,
  • R and R together very particularly preferably represent a C 5 -C 6 alkylene radical in which ⁇ : a methylene group is optionally replaced by oxygen.
  • X. stands especially for chlorine or bromine.
  • Y stands in particular for methyl
  • A, B and the carbon atom to which they are attached are in particular saturated Cg-cycloalkyl, in which a methylene group is optionally replaced by oxygen and which is optionally simply by methoxy, ethoxy, n-propoxy, iso-propoxy, n-butoxy or iso Butoxy is substituted,
  • G in particular represents hydrogen (a) or one of the groups
  • M oxygen or sulfur
  • R 1 in particular represents C 1 -C 6 -alkyl, C 1 -C 2 alkoxy-C 1 -C 2 -alkyl which is optionally monosubstituted to trisubstituted by fluorine or chlorine, or cyclopropyl,
  • R 2 stands especially for dd-alky! or d-Gr alkenyl
  • R 3 stands in particular for dG-alkyl.
  • Saturated or unsaturated hydrocarbon radicals such as alkyl, alkanediyl or alkenyl can also be used in connection with heteroatoms, e.g. in alkoxy, where possible, be straight-chain or branched.
  • Optionally substituted radicals can be mono- or polysubstituted, and in the case of multiple substitutions the substituents can be the same or different.
  • herbicide safeners of the formulas (Ila), (Hb), (He), (Eid) and (He) which improve the compatibility with crop plants are defined below.
  • m preferably represents the numbers 0, 1, 2, 3 or 4.
  • a 1 preferably represents one of the divalent heterocyclic groups outlined below
  • n preferably represents the numbers 0, 1, 2, 3 or 4.
  • a 2 preferably represents methylene or ethylene which is optionally substituted by methyl, ethyl, methoxycarbonyl, ethoxycarbonyl or allyloxycarbonyl.
  • R 14 preferably represents hydroxy, mercapto, amino, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methylthio, ethylthio, n- or i-propylthio, n-, i -, s- or t-butylthio, methylamino, ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino. Dimethylamino or diemylarnino.
  • R 15 preferably represents hydroxy, mercapto, amino, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, 1-methylhexyloxy, allyloxy, 1-allyloxymethyl-ethoxy, methylthio, ethyl - thio, n- or i-propylthio, n-, i-, s- or t-butylthio, methylamino, ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino, dimethylamino or diethylamino ,
  • R 16 ' preferably represents methyl, ethyl, n- or i-propyl, each optionally substituted by fluorine, chlorine and / or bromine.
  • R 17 preferably represents hydrogen, in each case optionally substituted by fluorine and / or chlorine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, propenyl, butenyl, propynyl or butynyl, methoxymethyl, Ethoxymethyl, methoxyethyl, ethoxyethyl, dioxolanylmethyl, furyl, furylmethyl, thienyl ,.
  • Thiazolyl, piperidinyl, or phenyl optionally substituted by fluorine, chlorine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl.
  • R 18 preferably represents hydrogen, in each case optionally substituted by fluorine and or chlorine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, propenyl, butenyl, propynyl or butynyl, methoxymethyl, ⁇ thoxymethyl , Methoxyethyl, ethoxyethyl, dioxolanylmethyl, furyl, furylmethyl, thienyl, thiazolyl, piperidinyl ,.
  • phenyl optionally substituted by fluorine, chlorine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, or together with R 1 ⁇ for one of the radicals -CH 2 -0-CH 2 -CH 2 - and -CH 2 -CH 2 -0-CH 2 -CH 2 -, which are optionally substituted by.
  • Methyl, ethyl, furyl, phenyl, a fused benzene ring or by two substituents which together with the carbon atom to which they are attached form a 5- or 6-membered carbocycle.
  • R 19 preferably represents hydrogen, cyano, fluorine, chlorine, bromine, or methyl, ethyl, n- or i-propyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl or phenyl, each optionally substituted by fluorine, chlorine and / or bromine ,
  • R 20 preferably represents hydrogen, optionally substituted by hydroxy, cyano, fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy methyl, ethyl, n- or i-propyl, n-, i-, s- or t- butyl.
  • R 21 preferably represents hydrogen, cyano, fluorine, chlorine, bromine, or methyl, ethyl, n- or i-propyl, n-, i-, s- or t- which is optionally substituted by fluorine, chlorine and / or bromine. Butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl or phenyl.
  • X 1 preferably represents nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, difluoromethyl, dichloromethyl, trifluoromethyl, trichloromethyl, chlorodifluoro- methyl, fluorodichloromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy or trifluoromethoxy.
  • X 2 preferably represents hydrogen, nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, difluoromethyl, dichloromethyl, trifluoromethyl, trichloromethyl, chlorodifluoromethyl , Fluorodichloromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy or trifluoromethoxy.
  • X 3 preferably represents hydrogen, nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, difluoromethyl, dichloromethyl, trifluoromethyl, trichloromethyl, chlorodifluoromethyl , Fluorodichloromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy or trifluoromethoxy.,
  • t preferably represents the numbers 0, 1, 2, 3 or 4.
  • v is preferably the number 0, 1, 2 or 3.
  • R 22 preferably represents hydrogen, methyl, ethyl, n- or i-propyl.
  • R 23 preferably represents hydrogen, methyl, ethyl, n- or i-propyl.
  • R 24 preferably represents hydrogen, in each case optionally substituted by cyano, fluorine, chlorine, methoxy, ethoxy, ⁇ - or i-propoxy-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl , Methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, Methylamines, ethylamino, n- or i-propylamino, n-, i-, s-, or t-butylamino, dimethylamino or diethylamino, or in each case optionally by cyano, fluorine, chlorine, bro
  • R 25 preferably represents hydrogen, in each case optionally methyl, ethyl, n- or i-propyl, n-, i- or s-butyl substituted by cyano, hydroxyl, fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy, propenyl, butenyl, propynyl or butynyl, optionally substituted by cyano, fluorine, chlorine or bromine, or cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl optionally substituted by cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl.
  • R 2 ⁇ preferably represents hydrogen, in each case optionally methyl, ethyl, n- or i-propyl, n-, i- or substituted by cyano, hydroxy, fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy s-butyl, in each case optionally substituted by cyano, fluorine, chlorine or bromine, propenyl, butenyl, propynyl or butinyl, each optionally by cyano, fluorine, chlorine, bromine, Methyl, ethyl, n- or i-propyl substituted cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl, or optionally by nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s - or t-butyl, tri
  • X 4 preferably represents nitro, cyano, carboxy, carbamoyl, formyl, sulfamoyl, hydroxy, amino, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl , Trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy or trifluoromethoxy.
  • X 5 preferably represents nitro, cyano, carboxy, carbamoyl, formyl, sulfamoyl, hydroxy, amino, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl , Trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy or trifluoromethoxy.
  • Table 2 examples of the compounds of the formula (Ha) which are particularly preferred as herbicide safeners according to the invention are listed in Table 2 below.
  • crop compatibility-improving compound [component (b)] are cloquintocet-mexyl, fenchlorazole-ethyl, isoxadifen-ethyl, mefenpyr-diethyl, furilazole, fenclorim, cumyluron, dymron, dimepiperate and the compounds He-5 and He-11 most preferred, with Cloquintocet-mexyl and Mefenpyr-diethyl being particularly emphasized.
  • the compounds of the general formula (Da) to be used according to the invention as safeners are known and / or can be prepared by processes known per se (cf. WO-A-91/07874, WO-A-95/07897).
  • the compounds of the general formula (Dd) to be used according to the invention as safeners are known and / or can be prepared by processes known per se (cf. DE-A-19621522 / US-A-6235680).
  • the compounds of the general formula (He) to be used according to the invention as safeners are known and can be prepared by processes known per se (cf. WO-A-99/66795 / US-A-6251827).
  • Examples of the selectively herbicidal combinations according to the invention, each comprising an active compound of the formula (T) and in each case one of the safeners defined above, are listed in Table 7 below.
  • A, B, X, Y, Z and R 8 have the meanings given above,
  • acylamino acid esters of the formula (H) are obtained, for example, if amino acid derivatives of the formula (XIV),
  • A, B and R 8 have the meanings given above,
  • A, B, X, Y and Z have the meanings given above,
  • A, B, X, Y and Z have the meanings given above,
  • halogenating agents for example thionyl chloride, thionyl bromide, oxalyl chloride, phosgene, phosphorus trichloride, phosphorus tribromide or phosphorus pentachloride
  • a diluent for example optionally chlorinated aliphatic or aromatic hydrocarbons such as toluene or methylene chloride
  • an acid e.g. an inorganic acid such as hydrochloric acid
  • a base e.g. an alkali hydroxide such as sodium or potassium hydroxide
  • a diluent e.g. an aqueous alcohol such as methanol or ethanol
  • the compounds of the formula (XIX) are also partly new and can be prepared by processes which are known in principle (WO 97/02243).
  • the compounds of the formula (XTX) are obtained, for example, by substituting 1,1,1-trichloro-2-phenylethanes of the formula (XX),
  • alcoholates e.g. alkali metal alcoholates such as sodium methylate or sodium ethylate
  • a diluent e.g. alcohol derived from the alcoholate
  • an acid preferably an inorganic acid such as sulfuric acid
  • a diluent e.g. an aliphatic nitrile such as acetonitrile
  • the compounds of the formula (XXI) are new and can be prepared by processes which are generally known in principle.
  • the compounds of the formula (XXH) are known compounds of organic chemistry. Copper (H) chloride and vinylidene chloride have long been known and can be bought.
  • the substituted cyclic aminocarboxylic acids of the formula (XVH), in which A and B form a ring, are generally obtainable after the Bucherer-Bergs synthesis or after the Strecker synthesis and are obtained in different isomer forms.
  • ⁇ the isomers in which the radicals R and the carboxyl group are in equatorial fashion are obtained
  • the isomers im following for the sake of simplicity referred to as ⁇ in which the amino group and the radicals R are equatorial.
  • A, B, X, Y, Z and R 8 have the meanings given above,
  • A, B, X, Y and Z have the meanings given above,
  • Process (A) is characterized in that compounds of the formula (H) in which A, B, X, Y, Z and R s have the meanings given above, in the presence of a diluent and in the presence of a base of an intramolecular condensation subjects.
  • Diluents which can be used in process (A) according to the invention are all organic solvents which are inert to the reactants.
  • Hydrocarbons such as toluene and xylene, furthermore ethers such as dibutyl ether, tetiahydrofuran, dioxane, glycol dimethyl ether and diglycol dimethyl ether, and also polar solvents such as dimethyl sulfoxide, sulfolane, dimethylformamide and N-methyl-pyrrolidone, and alcohols such as methanol, ethanol, are preferably usable.
  • All the usual proton acceptors can be used as the base (deprotonating agent) when carrying out process (A) according to the invention.
  • Alkali metals such as sodium or potassium can also be used.
  • Alkali metal and alkaline earth metal amides and hydrides such as sodium amide, sodium hydride and calcium hydride, and also alkali metal alcoholates, such as sodium methylate, sodium ethylate and potassium tert-butoxide, can also be used.
  • the reaction temperature can be varied within a substantial range when carrying out process (A) according to the invention. In general, temperatures between 0 ° C and 250 ° C, preferably between 50 ° C and 150 ° C.
  • Process (A) according to the invention is generally carried out under normal pressure.
  • reaction component of the formula (H) and the deprotonating base are generally employed in equimolar to approximately double-equimolar amounts. However, it is also possible to use one or the other component in a larger excess (up to 3 moles).
  • Process (B ⁇ ) is characterized in that compounds of the formula (I-a) are each reacted with carboxylic acid halides of the formula (in), if appropriate in the presence of a diluent and if appropriate in the presence of an acid binder.
  • All solvents which are inert towards the acid halides can be used as diluents in the process (B ⁇ ) according to the invention.
  • Hydrocarbons such as gasoline, benzene, toluene, xylene and tetralin are preferably usable, furthermore halogenated hydrocarbons such as methylene chloride, chloroform, carbon tetrachloride, chlorobenzene and o-dichlorobenzene, also ketones such as acetone and methylisopropyl ketone, furthermore ethers such as diethyl ether, tetrahydrofuran and dioxane, in addition carboxylic acid esters, such as ethyl acetate, and also strongly polar solvents, such as dimethyl sulfoxide and sulfolane. If the hydrolysis stability of the acid halide permits, the reaction can also be carried out in the presence of water.
  • Suitable acid binders for the reaction according to process (B ⁇ ) according to the invention are all customary acid acceptors.
  • Tertiary amines such as triethylamine, pyridine, diazabicyclooctane (DABCO), diazabicycloundecene (DBU), diazabicyclonones (DEN), Hunig base and N, N-dimethylaniline, and also alkaline earth metal oxides, such as magnesium and calcium oxide, are also preferably used Alkali and alkaline earth metal carbonates, such as sodium carbonate, potassium carbonate and calcium carbonate, and alkali metal hydroxides, such as sodium hydroxide and potassium hydroxide.
  • reaction temperature in process (B ⁇ ) according to the invention can be varied within a substantial range. In general, temperatures between -20 ° C and + 150 ° C, preferably between 0 ° C and 100 ° C.
  • Process (Bß) is characterized in that compounds of the formula (I-a) are each reacted with carboxylic anhydrides of the formula (TV), if appropriate in the presence of a diluent and if appropriate in the presence of an acid binder.
  • Suitable diluents for the process (Bß) according to the invention are preferably those diluents which are also preferred when using acid halides. Otherwise, an excess of carboxylic acid anhydride can also act as a diluent.
  • Suitable acid binders which may be added in process (Bß) are preferably those acid binders which are also preferred when using acid halides.
  • the reaction temperature can be varied within a substantial range in the process (Bß) according to the invention. In general, temperatures between -20 ° C and + 150 ° C, preferably between 0 ° C and 100 ° C.
  • the starting materials of the formula (I-a) and the carboxylic anhydride of the formula (IV) are generally used in approximately equivalent amounts in each case. However, it is also possible to use the carboxylic anhydride in a larger excess (up to 5 mol). The processing takes place according to usual methods.
  • the general procedure is to remove diluent and excess carboxylic acid anhydride and the carboxylic acid formed by distillation or by washing with an organic solvent or with water.
  • Process (C) is characterized in that compounds of the formula (I-a) are each reacted with chloroformate or chloroformate thiol ester of formula (V), if appropriate in the presence of a diluent and if appropriate in the presence of an acid binder.
  • Suitable acid binders in process (C) according to the invention are all customary acid acceptors.
  • Tertiary amines such as triethylamine, pyridine, DABCO, DBU, DBA, Hunig base and N, N-dimethylaniline, furthermore alkaline earth metal oxides, such as magnesium and calcium oxide, and also alkali and alkaline earth metal carbonates, such as sodium carbo- nate, potassium carbonate and calcium carbonate as well as alkali hydroxides such as sodium hydroxide and potassium hydroxide.
  • Diluents which can be used in process (C) according to the invention are all solvents which are inert to the chloroformates or chloroformates.
  • Hydrocarbons such as gasoline, benzene, toluene, xylene and tetralin, are preferably used, furthermore halogenated hydrocarbons, such as methylene chloride, chloroform, carbon tetrachloride, chlorobenzene and o-dichlorobenzene, and also ketones, such as acetone and methylisopropyl ketone, furthermore ethers, such as diethyl ether, tetrahydrofuran and Dioxane, in addition carboxylic acid esters, such as ethyl acetate, and also strongly polar solvents, such as dimethyl sulfoxide and sulfolane.
  • the reaction temperature can be when carrying out the process according to the invention. (C) can be varied within a wide range.
  • the reaction temperature is generally between -20 ° C and + 100 ° C, preferably between 0 ° C and 50 ° C.
  • Process (C) according to the invention is generally carried out under normal pressure.
  • the starting materials of the formula (I-a) and the corresponding chloroformic acid ester or chloroformic acid thiolester of the formula (V) are generally in each case used in approximately equivalent amounts. However, it is also possible to use one or the other component in a larger excess (up to 2 mol).
  • the processing takes place according to usual methods. The general procedure is to remove the precipitated salts and to concentrate the remaining reaction mixture by removing the diluent.
  • Process (D) is characterized in that compounds of the formula (Ia) are each reacted with (Da) compounds of the formula (VI) in the presence of a diluent and, if appropriate, in the presence of an acid binder or (Dß) carbon disulfide and then with alkyl halides of the formula (VH) if appropriate in the presence of a diluent and if appropriate in the presence of a base.
  • Possible diluents added are all inert polar organic solvents, such as ethers, esters, amides, sulfones, sulfoxides, but also haloalkanes. Dimethyl sulfoxide, ethyl acetate, tetrahydrofuran, dimethylformamide or methylene chloride are preferably used.
  • the addition of strong deprotonating agents such as e.g. Sodium hydride or potassium tert-butylate is the enolate salt of the compound (I-a), the further addition of acid binders can be dispensed with.
  • customary inorganic or organic bases are suitable, examples being sodium hydroxide, sodium carbonate, potassium carbonate, pyridine and triethylamine.
  • the reaction can be carried out under normal pressure or under elevated pressure, preferably under normal pressure.
  • the processing takes place according to usual methods.
  • the equimolar amount or an excess of carbon disulfide is added per mole of starting compounds of the formula (I-a).
  • the process is preferably carried out at temperatures from 0 to 50 ° C. and in particular at 20 to 30 ° C.
  • Alkali metal hydrides, alkali metal alcoholates, alkali metal or alkaline earth metal carbonates or hydrogen carbonates or nitrogen bases are preferably usable.
  • Examples include sodium hydride, sodium methoxide, sodium hydroxide, calcium hydroxide, potassium carbonate, sodium hydrogen carbonate, triemylamine, dibenzylamine, diisopropylethylamine, pyridine, quinoline, diazabicyclooctane (DABCO), diazabicyclonones (DBN) and diazabicycloundecene (DBU).
  • Aromatic hydrocarbons such as benzene or toluene, alcohols such as methanol, ethanol, isopropanol or ethylene glycol, nitriles such as acetonitrile, ethers such as tetrahydrofuran or dioxane, amides such as dimethylformamide or other polar solvents such as dimethyl sulfoxide or sulfolane can preferably be used.
  • the further reaction with the alkyl halide of the formula (VH) is preferably carried out at 0 to 70 ° C. and in particular at 20 to 50 ° C.
  • at least the equimolar amount of alkyl halide is used.
  • the processing is again carried out using customary methods.
  • Process (E) according to the invention is characterized in that compounds of the formula (I-a) are each reacted with sulfonic acid chlorides of the formula (VHI), if appropriate in the presence of a diluent and if appropriate in the presence of an acid binder.
  • Process (E) is preferably carried out in the presence of a diluent.
  • Suitable diluents are all inert polar organic solvents such as ethers, esters, amides, nitriles, sulfones, sulfoxides or halogenated hydrocarbons such as methylene chloride.
  • Dimethyl sulfoxide, tetrahydrofuran, ethyl acetate, dimethylformamide, methylene chloride are preferably used.
  • the enolate salt of the compound (I-a) is prepared by adding strong deprotomerizing agents (such as sodium hydride or potassium tertiary butoxide), the further addition of acid binders can be dispensed with.
  • strong deprotomerizing agents such as sodium hydride or potassium tertiary butoxide
  • customary inorganic or organic bases are suitable, examples being sodium hydroxide, sodium carbonate, potassium carbonate, pyridine and triethylamine.
  • the reaction can be carried out under normal pressure or under elevated pressure, preferably under normal pressure.
  • the processing takes place according to usual methods.
  • Process (F) according to the invention is characterized in that compounds of the formula (I-a) are each reacted with phosphorus compounds of the formula (IX), if appropriate in the presence of a diluent and if appropriate in the presence of an acid binder.
  • Process (F) is preferably carried out in the presence of a diluent.
  • Suitable diluents are all inert, polar organic solvents such as ethers, esters, amides, nitriles, sulfides, sulfones, sulfoxides etc.
  • Acetonitrile, ethyl acetate, dimethyl sulfoxide, tetrahydrofuran, dimethylformamide, methylene chloride are preferably used.
  • Possible inorganic binders which may be added are conventional inorganic or organic bases, such as hydroxides, carbonates or amines. Examples include sodium hydroxide, sodium carbonate, potassium carbonate, pyridine and triethylamine.
  • the reaction can be carried out under normal pressure or under elevated pressure, preferably under normal pressure.
  • the processing takes place according to the usual methods of organic chemistry.
  • the end products are preferably obtained by crystallization, chromatographic purification or by so-called “distillation", i.e. Removal of volatile components cleaned in vacuo.
  • Process (G) is characterized in that compounds of the formula (I-a) are each reacted with metal hydroxides or metal alkoxides of the formula (X) or amines of the formula (XI), if appropriate in the presence of a diluent.
  • Diluents which can be used in process (G) according to the invention are preferably ethers such as tetrahydrofuran, dioxane, diethyl ether or alcohols such as methanol, ethanol, isopropanol, but also water.
  • Process (G) according to the invention is generally carried out under normal pressure.
  • the reaction temperature is generally between -20 ° C and 100 ° C, preferably between 0 ° C and 50 ° C.
  • Process (H) is characterized in that compounds of the formula (Ia) are each treated with (H ⁇ ) compounds of the formula (XU) optionally in the presence of a diluent and optionally in the presence of a catalyst or (Hß) with compounds of the formula (XID ) if appropriate in the presence of a diluent and if appropriate in the presence of an acid binder.
  • Process (H ⁇ ) is preferably carried out in the presence of a diluent.
  • Suitable diluents are all inert organic solvents, such as ethers, esters, amides, nitriles, sulfones or sulfoxides. If necessary, catalysts can be added to accelerate the reaction. Organotin compounds such as dibutyltin dilaurate can be used very advantageously as catalysts.
  • inert polar organic solvents such as ethers, esters, amides, sulfones, sulfoxides or halogenated hydrocarbons, are suitable as diluents, if appropriate.
  • Dimethyl sulfoxide, ethyl acetate, tetrahydrofuran, dimethylformamide or methylene chloride are preferably used.
  • the enolate salt of the compound (I-a) is prepared by adding strong deprotonating agents (such as sodium hydride or potassium tert-butoxide), the further addition of acid binders can be dispensed with.
  • strong deprotonating agents such as sodium hydride or potassium tert-butoxide
  • customary inorganic or organic bases are suitable, for example sodium hydroxide, sodium carbonate, potassium carbonate, triethylamine or pyridine.
  • the reaction can be carried out under normal pressure or under elevated pressure, preferably under normal pressure.
  • the processing takes place according to usual methods.
  • the active substances are suitable for combating animal pests, in particular insects, arachnids and nematodes, which occur in agriculture, in forests, in the protection of stored goods and materials, and in the hygiene sector. They can preferably be used as pesticides. They are effective against normally sensitive and resistant species as well as against all or individual stages of development.
  • the pests mentioned above include:
  • Isopoda e.g. Oniscus asellus, Armadillidium vulgare, Porcellio scaber.
  • Symphyla for example, Scutigerella immaculata.
  • Thysanura for example Lepisma saccharina.
  • Orthoptera e.g. Acheta domesticus, Gryllotalpa spp., Locusta migratoria migratorioides, Melanoplus spp., Schistocerca gregaria.
  • Phthiraptera e.g. Pediculus humanus corporis, Haematopinus spp., Linognathus spp., Trichodectes spp., Damalinia spp.
  • Thysanoptera e.g. Hercmothrips femoralis, Thrips tabaci, Thrips palmi, Frankliniella occidentalis.
  • Homoptera e.g.
  • Hymenoptera e.g. Diprion spp., Hoplocampa spp., Lasius spp., Monomorium pharaonis, Vespa spp.
  • Chorioptes spp. Sarcoptes spp., Tarsonemus spp., Bryobia praetiosa, Panonychus spp., Tetranychus spp., Hemitarsonemus spp., Brevipalpus spp.
  • Plant parasitic nematodes include e.g. Pratylenchus spp., Radopholus similis, Ditylenchus dipsaci, Tylenchulus semipenetrans, Heterodera spp., Globodera spp., Meloidogyne spp., Aphelenchoides spp., Longidorus spp., Xiphinema spp., Trichodorus spp., Bursaph.
  • the compounds or combinations of active substances according to the invention can optionally also be used as herbicides in certain concentrations or application rates. If appropriate, the compounds can also be used as intermediates or precursors for the synthesis of further active compounds.
  • Plants are understood here to mean all plants and plant populations, such as desired and wanted wild plants or crops (including naturally occurring crops).
  • Crop plants can be plants which can be obtained by conventional breeding and optimization methods or by biotechnological and genetic engineering methods or combinations of these methods, including the transgenic plants and including the plant cultivars which can or cannot be protected by plant breeders' rights.
  • Plant parts are to be understood to mean all above-ground and underground parts and organs of the plants, such as shoots, leaves, flowers and roots, examples being leaves, needles, stems, stems, flowers, fruiting bodies, fruits and seeds as well as roots, tubers and rhizomes.
  • the plant parts also include crops and vegetative and generative propagation material, for example cuttings, tubers, rhizomes, offshoots and seeds.
  • the treatment of the plants and plant parts according to the invention with the active substances or combinations of active substances takes place directly or by acting on their surroundings, living space or storage space according to the usual treatment methods, e.g. by dipping, spraying, spraying, vaporizing, atomizing, scattering, spreading and, in the case of propagation material, in particular in the case of seeds, furthermore by coating in one or more layers.
  • the active ingredients or combinations of active ingredients can be converted into the customary formulations, such as solutions, emulsions, wettable powders, suspensions, powders, dusts, pastes, soluble powders, granules, suspension emulsion concentrates, active ingredient-impregnated natural and synthetic substances and very fine encapsulations polymeric fabrics.
  • formulations are made in a known manner, e.g. by mixing the active ingredients with extenders, that is to say liquid solvents and / or solid carriers, optionally using surface-active agents, that is to say emulsifiers and / or dispersants and / or foam-generating agents.
  • extenders that is to say liquid solvents and / or solid carriers
  • surface-active agents that is to say emulsifiers and / or dispersants and / or foam-generating agents.
  • organic solvents can also be used as auxiliary solvents.
  • auxiliary solvents e.g. organic solvents
  • aromatics such as xylene, toluene, or alkylnaphthalenes
  • chlorinated aromatics and chlorinated aliphatic hydrocarbons such as chlorobenzenes, chlorethylenes or methylene chloride
  • aliphatic hydrocarbons such as cyclohexane or paraffins, e.g.
  • Petroleum fractions mineral and vegetable oils, alcohols such as butanol or glycol as well as their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents such as dimethylformamide and dimethyl sulfoxide, and water.
  • solid carriers e.g. ammonium salts and natural rock powders, such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and synthetic rock powders, such as highly disperse silica, aluminum oxide and silicates, as solid carriers for granulates are possible: e.g.
  • emulsifiers and or foam-generating agents are: for example non-ionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates and protein hydrolyzates; The following may be used as dispersants: for example lignin sulfite waste liquor and methyl cellulose.
  • Adhesives such as carboxymethyl cellulose, natural and synthetic powdery, granular or latex-shaped polymers, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, and natural phospholipids such as cephalins and lecithins and synthetic phospholipids can be used in the formulations.
  • Other additives can be mineral and vegetable oils.
  • Dyes such as inorganic pigments, e.g. Iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin, azo and metal phthalocyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc can be used.
  • the formulations generally contain between 0.1 and 95 wt .-% ⁇ active compound, preferably between 0.5 and 90%.
  • the active compounds according to the invention can also be used in a mixture with known fungicides, bactericides, acaricides, nematicides or insecticides, in order, for example, to to broaden the spectrum of activity or to prevent the development of resistance.
  • fungicides bactericides
  • acaricides nematicides or insecticides
  • synergistic effects are obtained, i.e. the effectiveness of the mixture is greater than the effectiveness of the individual components.
  • Debacarb dichlorophene, diclobutrazole, diclofluanide, diclomezin, dicloran, diethofencarb, difenoconazole, dimetbirimol, dimethomorph, diniconazole, diniconazol-M, dinocap, diphenylamine, dipyrithione, ditalimfos, dorphianzolodonodonodine
  • Imazalil Lnibenconazol, Iminoctadin, Iminoctadinealbesilat, Iminoctadinetriacetat, Iodocarb, Ipconazol, Iprobefos (IBP), Iprodione, Irumamycm, Isoprothiolan, Isovaledione,
  • Mancopper Mancozeb, Maneb, Meferimzone, Mepanipyrim, Mepronil, Metalaxyl, Metconazol, Methasulfocarb, Methfuroxam, Metiram, Metomeclam, Metsulfovax, Mildiomycin, Myclobutanil, Myclozolin,
  • Oxadixyl Oxamocarb, Oxolinicacid, Oxycarboxim, Oxyfenthiin,
  • Paclobutrazole pefurazoate, penconazole, pencycuron, Phosdiphen, picoxystrobin, pimaricin, piperalin, polyoxin, polyoxorim, probenazole, prochloraz, procymidon, propamocarb, propanosine sodium,
  • Fenamiphos Fenazaquin, Fenbutatin oxide, Fenitrothion, Fenothiocarb, Fenoxacrim, Fenoxycarb, Fenpropathrin, Fenpyrad, Fenpyrithrin, Fenpyroximate, Fenvalerate, Fipronil, Fluazinam, Fluazuron, Flubrocythrinate, Flucycloxuron, Fluthrinoxin, Fluutinoxin, Fluutinoxin , Fubfenprox, Furathiocarb, granulosis
  • Halofenozide HCH, Heptenophos, Hexaflumuron, Hexythiazox, Hydroprene,
  • Mecarbam Metaldehyde, Methamidophos, Metharhician anisopliae, Metharhician flavoviride, Methidathione, Methiocarb, Methoprene, Methomyl, Methoxyfenozide, Metolcarb, Metoxadiazone, Mevinphos, Milbemectin, Milbemycin, Monocrotophos,
  • Paecilomyces fumosoroseus Parathion A, Parathion M, Permethrin, Phenthoat, Phorat, Phosalone, Phosmet, Phosphamidon, Phoxim, Pirimicarb, Pirimiphos A, Pirimiphos M, Profenofos, Promecarb, Propargite, Propoxur, Prothiofos, Prothrohrinos, Pothrohrinos, Pothrohrinos, Pothrohrinos, Pothrohrinos , Pyridaben, pyridathione, pyrimidifen, pyriproxyfen,
  • the active compounds according to the invention can furthermore be present in their commercially available formulations and in the use forms prepared from these formulations in a mixture with synergists.
  • Synergists are compounds that increase the effectiveness of the active ingredients without the added synergist itself having to be active.
  • the active substance content of the use forms prepared from the commercially available formulations can vary within wide ranges.
  • the active substance concentration of the use forms can be from 0.0000001 to 95% by weight of active substance, preferably between 0.0001 and 1% by weight.
  • the application takes place in a customary manner adapted to the application forms.
  • the active ingredient or combination of active ingredients When used against hygiene pests and pests of stored products, the active ingredient or combination of active ingredients is distinguished by an excellent residual action on wood and clay and by a good stability to alkali on limed substrates.
  • all plants and their parts can be treated.
  • wild plant species or plant species and their parts obtained by conventional biological breeding methods such as crossing or protoplast fusion
  • transgenic plants and plant cultivars which have been obtained by genetic engineering methods if appropriate in combination with conventional methods (genetic modified organisms) and their parts are treated.
  • the term "parts” or “parts of plants” or “plant parts” was explained above.
  • Plants of the plant varieties which are in each case commercially available or in use are particularly preferably treated according to the invention.
  • Plant varieties are plants with new traits that have been grown by conventional breeding, by mutagenesis or by recombinant DNA techniques. These can be varieties, bio and genotypes.
  • the treatment according to the invention can also cause superadditive (“synergistic") effects.
  • superadditive for example, reduced application rates and / or widening of the spectrum of action and / or an increase in the action of the substances and agents which can be used according to the invention, better plant growth, increased tolerance to high or low temperatures, increased tolerance to dryness or to water or soil salt content, increased flowering performance , easier harvesting, acceleration of ripeness, higher crop yields, higher quality and / or higher nutritional value of the harvested products, higher storability and / or workability of the harvested products possible, which go beyond the effects to be expected.
  • the preferred transgenic (genetically engineered) plants or plant cultivars to be treated according to the invention include all plants which, through the genetic engineering modification, have received genetic material which gives these plants particularly advantageous, valuable properties (“traits”). Examples of such properties are better plant growth, increased tolerance to high or low temperatures, increased tolerance to drought or to water or soil salt content, increased flowering performance, easier harvesting, accelerated ripening, higher crop yields, higher quality and / or higher nutritional value of the harvested products , higher shelf life and / or workability of the harvested products.
  • transgenic plants are the important cultivated plants, such as cereals (wheat, rice), corn, soybeans, potatoes, cotton, rapeseed, beets, sugar cane and fruit plants (with the fruits apples, pears, citrus fruits and grapes), with maize , Soy, potato, cotton and rapeseed are particularly highlighted.
  • the traits are particularly emphasized as the increased defense of the plants against insects by toxins which arise in the plants, in particular those which are caused by the genetic material from Bacillus thuringiensis (for example by the genes Cry ⁇ A (a), CryIA (b), Cry ⁇ A (c), CryHA, CrylUA, CryIHB2, Cry9c Cry2Ab, Cry3Bb and CrylF as well as their combinations) are produced in the plants (hereinafter "Bt plants”).
  • the properties (“traits”) also particularly emphasize the increased defense of plants against fungi, bacteria and viruses through systemic acquired resistance (SAR), systemin, Phytoalexins, elicitors as well as resistance genes and correspondingly expressed proteins and toxins.
  • the properties (“traits”) which are particularly emphasized are the increased tolerance of the plants to certain herbicidal active compounds, for example imidazolinones, sulfonylureas, glyphosate or phosphinotricin (for example “PAT” gene).
  • the genes conferring the desired properties (“traits”) can also occur in combinations with one another in the transgenic plants.
  • Examples of “Bt plants” are corn varieties, cotton varieties, soy varieties and potato varieties that are sold under the trade names YTELD GARD® (e.g. corn, cotton, soy), KnockOut® (e.g. corn), StarLink® (e.g. corn), Bollgard® ( Cotton), Nucotn® (cotton) and NewLeaf® (potato).
  • herbicide-tolerant plants are corn varieties, cotton varieties and soy varieties that are sold under the trade names Roundup Ready® (tolerance against glyphosate e.g. corn, cotton, soy), Liberty Link® (tolerance against phosphinotricin, e.g. rape), EVA® (tolerance against Imidazolinone) and STS® (tolerance to sulfonylureas such as maize).
  • the herbicide-resistant plants (conventionally bred to herbicide tolerance) include the varieties marketed under the name Clearf ⁇ eld® (eg maize). Of course, these statements also apply to plant varieties developed in the future or coming onto the market in the future with these or future-developed genetic properties ("traits").
  • the plants listed can be treated particularly advantageously with the compounds according to the invention or the active compound mixtures according to the invention.
  • the preferred ranges given above for the active substances or mixtures also apply to the treatment of these plants. Plant treatment with the compounds or mixtures specifically listed in the present text should be particularly emphasized.
  • the active substances or combinations of active substances according to the invention act not only against plant, hygiene and stored-product pests, but also in the veterinary sector against animal parasites (ectoparasites) such as tick ticks, leather ticks, space mites, running mites, flies (stinging and licking), parasitic fly larvae and lice , Hair lice, featherlings and fleas.
  • animal parasites ectoparasites
  • tick ticks such as tick ticks, leather ticks, space mites, running mites, flies (stinging and licking), parasitic fly larvae and lice , Hair lice, featherlings and fleas.
  • parasites include:
  • Anoplurida e.g. Haematopinus spp., Linognathus spp., Pediculus spp., Phtirus spp., Solenopotes spp ..
  • Nematocerina and Brachycerina for example Aedes spp., Anopheles spp., Culex spp., Simulium spp., Eusimulium spp., Phlebotomus spp., Lutzomyia spp., Culicoides spp., Chrysops spp., Hybomitra spp.
  • Atylotus spp. Tabanus spp., Haematopota spp., Philipomyia spp., Braula spp., Musca spp., Hydrotaea spp., Stomoxys spp., Haematobia spp., Morellia spp., Fannia spp., Glossina spp., Calliphora spp., Lucilia spp., Chrysomyia spp., Wohlfahrtia spp., Sarcophaga spp., Oestrus spp., Hypoderma spp., Gasterophilus spp., Hippobosca spp., Lipoptena spp., Melophagus spp ..
  • Siphonaptrida e.g. Pulex spp., Ctenocephalides spp., Xenopsylla spp., Ceratophyllus spp ..
  • Actinedida Prostigmata
  • Acaridida e.g. Acarapis spp., Cheyletiella spp., Ornitrocheyletia spp., Myobia spp., Psorergates spp., Demodex spp., Trombicula spp., Listrophorus spp., Acarus spp., Tyrophagus spp., Caloglyphus spp., Hypodterol spp ., Psoroptes spp., Chorioptes spp., Otodectes spp., Sarcoptes spp., Notoedres spp., Knemidocoptes spp., Cytodites spp., Laminosioptes spp ..
  • the active substances or combinations of active substances according to the invention are also suitable for combating arthropods which are used in agricultural animals such as e.g. Cattle, sheep, goats, horses, pigs, donkeys, camels, buffalo, rabbits, chickens, turkeys, ducks, geese, bees, other pets such as e.g. Dogs, cats, house birds, aquarium fish and so-called experimental animals, such as Infest hamsters, guinea pigs, rats and mice.
  • arthropods By combating these arthropods, deaths and reduced performance (in the case of meat, milk, wool, skins, eggs, honey, etc.) are to be reduced, so that the use of the active compounds according to the invention enables more economical and simple animal husbandry.
  • the active compounds or combinations of active compounds according to the invention are used in the veterinary sector in a known manner by enteral administration in the form of, for example, tabs.
  • enteral administration in the form of, for example, tabs.
  • parenteral administration such as by injections (intramuscular, subcutaneous, intravenous, intraperitoneal, etc.), implants
  • nasal application by dermal application in the form of, for example, diving or bathing (dipping), spraying (spray), pouring on (pour-on and spot-on), washing, powdering and with the help of shaped articles containing active ingredients, such as collars, ear tags, tail marks, limb bands , Holsters, marking devices etc.
  • the active ingredients or combinations of active ingredients can be formulated (for example powders, emulsions, flowable agents) which contain the active ingredients in an amount of 1 to 80% by weight, directly or after 100 Apply up to 10,000-fold dilution or use it as a chemical bath.
  • insects may be mentioned by way of example and preferably, but without limitation:
  • Kalotermes flavicollis Cryptotermes brevis, Heterotermes indicola, Reticulitermes flavipes, Reticulitermes santonensis, Reticulitermes lucifugus, Mastotermes darwiniensis, Zootermopsis nevadensis, Coptotermes formosanus.
  • Bristle tails such as Lepisma saccharina.
  • technical materials are to be understood as non-living materials, such as preferably plastics, adhesives, glues, papers and cartons, leather, wood, wood processing products and paints.
  • the material to be protected from insect infestation is very particularly preferably wood and wood processing products.
  • Wood and wood processing products which can be protected by the agent according to the invention or mixtures containing it are to be understood as examples:
  • the active substances or combinations of active substances can be used as such, in the form of concentrates or generally customary formulations such as powders, granules, solutions, suspensions, emulsions or pastes.
  • the formulations mentioned can be prepared in a manner known per se, e.g. by mixing the active ingredients / with at least one solvent or diluent, emulsifier, dispersant and / or binder or fixative, water repellent, optionally siccatives and UV stabilizers and optionally dyes and pigments and further processing aids.
  • the insecticidal compositions or concentrates used to protect wood and wood-based materials contain the active ingredient according to the invention in a concentration of 0.0001 to 95% by weight, in particular 0.001 to 60% by weight.
  • the amount of the agents or concentrates used depends on the type and occurrence of the insects and on the medium. The optimum amount of use can be determined in each case by test series. In general, however, it is sufficient to use 0.0001 to 20% by weight, preferably 0.001 to 10% by weight, of the active ingredient, based on the material to be protected.
  • An organic chemical solvent or serves as a solvent and / or diluent
  • Solvent mixture and / or an oily or oily low volatile organic chemical solvent or solvent mixture and / or a polar organic chemical Solvent or solvent mixture and / or water and optionally an emulsifier and / or wetting agent.
  • the organic chemical solvents used are preferably oily or oily solvents with an evaporation number above 35 and a flash point above 30 ° C., preferably above 45 ° C.
  • Corresponding mineral oils or their aromatic fractions or mineral oil-containing solvent mixtures, preferably white spirit, petroleum and / or alkylbenzene, are used as such low-volatility, water-insoluble, oily and oily solvents.
  • Mineral oils with a boiling range of 170 to 220 ° C, white spirit with a boiling range of 170 to 220 ° C, spindle oil with a boiling range of 250 to 350 ° C, petroleum or aromatics with a boiling range of 160 to 280 ° C, Te ⁇ entinöl and Like. Used.
  • liquid aliphatic hydrocarbons with a boiling range from 180 to 210 ° C. or high-boiling mixtures of aromatic and aliphatic hydrocarbons with a boiling range from 180 to 220 ° C. and / or locker oil and / or monochloronaphthalene, preferably ⁇ -monochloronaphthalene, are used.
  • organic low-volatility oily or oily solvents with an evaporation number above 35 and a flash point above 30 ° C, preferably above 45 ° C can be partially replaced by slightly or medium-volatile organic chemical solvents, with the proviso that the solvent mixture also has an evaporation number 35 and a flash point above 30 ° C, preferably above 45 ° C, and that the insecticide-fungicide mixture is soluble or emulsifiable in this solvent mixture.
  • part of the organic chemical solvent or solvent mixture is replaced by an aliphatic polar organic chemical solvent or solvent mixture.
  • Aliphatic organic chemical solvents containing hydroxyl and / or ester and / or ether groups, such as, for example, glycol ethers, esters or the like, are preferably used.
  • the organic-chemical binders used are the water-thinnable synthetic resins which are known per se and / or which are soluble or dispersible or emulsifiable in the organic chemical solvents used and / or binding drying oils, in particular binders consisting of or containing an acrylate resin, a vinyl resin, for example polyvinyl acetate, polyester resin, polycondensation or polyaddition resin, polyurethane resin, alkyd resin or modified alkyd resin, phenolic resin, hydrocarbon resin such as inden-coumarone resin, silicone resin, drying vegetable and / or drying oils and / or physically drying binders based on a natural and / or synthetic resin.
  • binders consisting of or containing an acrylate resin, a vinyl resin, for example polyvinyl acetate, polyester resin, polycondensation or polyaddition resin, polyurethane resin, alkyd resin or modified alkyd resin, phenolic resin, hydrocarbon resin such as inden-coumarone
  • the synthetic resin used as a binder can be used in the form of an emulsion, dispersion or solution. Bitumen or bituminous substances up to 10% by weight can also be used as binders. In addition, known dyes, pigments, water-repellants, odor correctors and inhibitors or anticorrosive agents and the like can be used.
  • At least one alkyd resin or modified alkyd resin and / or a drying vegetable oil is preferably contained in the agent or in the concentrate as the organic chemical binder.
  • Alkyd resins with an oil content of more than 45% by weight, preferably 50 to 68% by weight, are preferably used according to the invention.
  • binder mentioned can be replaced by a fixing agent (mixture) or a plasticizer (mixture). These additives are intended to prevent volatilization of the active ingredients and crystallization or precipitation. They preferably replace 0.01 to 30% of the binder (based on 100% of the binder used).
  • the plasticizers come from the chemical classes of phthalic acid esters such as dibutyl, dioctyl or benzyl butyl phthalate, phosphoric acid esters such as tributyl phosphate, adipic acid esters such as di- (2-ethylhexyl) adipate, stearates such as butyl stearate or amyl stearate, oleates such as butyl oleate, higher glycerol glycol or glycerol ether and p-toluenesulfonic acid ester.
  • phthalic acid esters such as dibutyl, dioctyl or benzyl butyl phthalate
  • phosphoric acid esters such as tributyl phosphate
  • adipic acid esters such as di- (2-ethylhexyl) adipate
  • stearates such as butyl stearate or amyl
  • Fixing agents are chemically based on polyvinyl alkyl ethers such as e.g. Polyvinyl methyl ether or ketones such as benzophenone, ethylene benzophenone.
  • Water is also particularly suitable as a solvent or diluent, optionally in a mixture with one or more of the above-mentioned organic chemical solvents or diluents, emulsifiers and dispersants.
  • a particularly effective wood protection is achieved through industrial impregnation processes, e.g. Vacuum, double vacuum or pressure process.
  • the ready-to-use compositions may optionally contain further insecticides and, if appropriate, one or more fungicides.
  • insecticides and fungicides mentioned in WO 94/29 268 are preferably suitable as additional mixing partners.
  • the compounds mentioned in this document are an integral part of the present application.
  • Insecticides such as Chlo ⁇ yriphos, Phoxim, Silafluofin, Alphamethrin, Cyfluthrin, Cypermethrin, Deltamethrin, Permethrin, Imidacloprid, NI-25, Flufenoxuron, Hexaflumuron, Transfluthrin, Methoxyphenuroprid, Thiacloxiduron
  • fungicides such as epoxyconazole, hexaconazole, azaconazole, propiconazole, tebuconazole, cyproconazole, metconazole, imazalil, dichlorofluoride, tolylfluanid, 3-iodo-2-propynylbutylcarbamate, N-octyl-isothiazolin-3-one and 4,5-dichloro octylisothiazolin-3-one.
  • the compounds or combinations of active substances according to the invention can be used to protect objects, in particular ship hulls, sieves, nets, structures, quay systems and signaling systems which come into contact with sea or brackish water.
  • Ledamo ⁇ ha barnacles
  • Balanomo ⁇ ha barnacles
  • Baianus or Pollicipes species increases the frictional resistance of Ships and subsequently leads to a significant increase in operating costs due to increased energy consumption and, moreover, frequent dry dock stays.
  • heavy metals such as e.g. in bis (trialkyltin) sulfides, tri-butyltin laurate, tri-butyltin chloride, copper (I) oxide, triethyltin chloride, tri-butyl (2-phenyl-4-chlorophenoxy) tin, tributyltin oxide, molybdenum disulfide, antimony oxide, polymeric butyl titanate, phenyl- (bispyridine) -wismutchlorid, tri-H-butylzinnfluorid, Manganethylenbisthio- carbamate, zinc dimethyldithiocarbamate, Zinkethylenbisthiocarbamat, zinc and copper salts of 2-pyridinethiol-1-oxide, Bisdimethyldithiocarbamoylzinkethylenbisthiocarbamat, zinc oxide, copper (
  • the ready-to-use antifouling paints can optionally contain other active ingredients, preferably contain algicides, fungicides, herbicides, molluscicides or other antifouling active ingredients.
  • the antifouling agents used contain the active compound according to the invention of the compounds according to the invention in a concentration of 0.001 to 50% by weight, in particular 0.01 to 20% by weight.
  • the antifouling agents according to the invention furthermore contain the usual constituents, such as in Ungerer, Chem. Ind. 1985, 37, 730-732 and Williams, Antifouling Marine Coatings, Noyes, ParkRidge, 1973.
  • antifouling paints contain in particular binders.
  • binders are polyvinyl chloride in a solvent system, chlorinated rubber in a solvent system, acrylic resins in a solvent system, in particular in an aqueous system, vinyl chloride / vinyl acetate copolymer systems in the form of aqueous dispersions or in the form of organic solvent systems, butadiene / styrene / acrylonitrile Rubbers, drying oils, such as linseed oil, resin esters or modified hard resins in combination with tar or bitumen, asphalt and epoxy compounds, small amounts of chlorinated rubber, chlorinated polypropylene and vinyl resins.
  • Paints may also contain inorganic pigments, organic pigments or dyes, which are preferably insoluble in seawater. Paints may also contain materials, such as rosin, to enable controlled release of the active ingredients. The paints may also contain plasticizers, modifiers affecting theological properties, and other conventional ingredients. The compounds according to the invention or the mixtures mentioned above can also be incorporated into self-polishing antifouling systems.
  • the active substances or combinations of active substances are also suitable for controlling animal pests, in particular insects, arachnids and mites, which live in closed rooms, such as, for example, apartments, factory halls, offices, vehicle cabins and the like. occurrence. To combat these pests, they can be used alone or in combination with other active ingredients and auxiliaries in household insecticide products. They are effective against sensitive and resistant species and against all stages of development. These pests include:
  • Sco ⁇ ionidea e.g. Buthus occitanus.
  • Acarina e.g. Argas persicus, Argas reflexus, Bryobia ssp., Dermanyssus gallinae, Glyciphagus domesticus, Omithodorus moubat, Rhipicephalus sanguineus, Trombicula alfreddugesi, Neutrombicula autumnalis, Dermatophagoides pteronissimus, Dermatophagoides forinae.
  • Opiliones e.g. Pseudosco ⁇ iones chelifer, Pseudosco ⁇ iones cheiridium, Opiliones phalangium.
  • Diplopoda e.g. Blaniulus guttulatus, Polydesmus spp ..
  • Chilopoda for example Geophilus spp .
  • Zygentoma for example Ctenolepisma spp., Lepisma saccharina, Lepismodes inquilinus.
  • Lepidoptera e.g. Achroia grisella, Galleria mellonella, Plodia inte ⁇ unctella, Tinea cloacella, Tinea pellionella, Tineola bisselliella.
  • Ctenocephalides canis Ctenocephalides felis, Pulex irritans, Tunga penetrans, Xenopsylla cheopis.
  • Hymenoptera e.g. Camponotus herculeanus, Lasius fuliginosus, Lasius niger, Lasius umbratus, Monomorium pharaonis, Paravespula spp., Tetramorium caespitum.
  • the active compounds or combinations of active compounds according to the invention can also be used as defoliants, desiccants, haulm killers and in particular as weed killers. Weeds in the broadest sense are understood to mean all plants that grow up in places where they are undesirable. Whether the substances according to the invention act as total or selective herbicides depends essentially on the amount used.
  • the active substances or combinations of active substances according to the invention can e.g. can be used in the following plants:
  • the active compounds or combinations of active compounds according to the invention are suitable for combating total weeds, e.g. on industrial and track systems and on paths and squares with and without tree cover.
  • the active compounds according to the invention for weed control in permanent crops e.g. Forest, ornamental wood, fruit, wine, citrus, nut, banana, coffee, tea, rubber, oil palm, cocoa, berry fruit and hop plants, on ornamental and sports turf and pasture land and for selective purposes Weed control can be used in annual crops.
  • the compounds or combinations of active substances according to the invention show strong herbicidal activity and a broad spectrum of activity when used on the soil and on above-ground parts of plants. To a certain extent, they are also suitable for the selective control of monocot and dicot weeds in monocot and dicot crops, both in the pre-emergence and in the post-emergence process.
  • the active substances or combinations of active substances according to the invention can also be used in certain concentrations or application rates for controlling animal pests and fungal or bacterial plant diseases. If appropriate, they can also be used as intermediates or products for the synthesis of further active ingredients.
  • the active ingredients or combinations of active ingredients can be converted into the customary formulations, such as solutions, emulsions, wettable powders, suspensions, powders, dusts, pastes, soluble powders, granules, suspension emulsion concentrates, active ingredient-impregnated natural and synthetic substances and very fine encapsulations polymeric fabrics.
  • formulations are prepared in a known manner, e.g. B. by mixing the active ingredients with extenders, that is liquid solvents and / or solid carriers, optionally using surface-active agents, ie emulsifiers and / or dispersants and / or foam-generating agents.
  • extenders that is liquid solvents and / or solid carriers
  • surface-active agents ie emulsifiers and / or dispersants and / or foam-generating agents.
  • organic solvents can, for example, also be used as auxiliary solvents.
  • auxiliary solvents include aromatics, such as xylene, toluene, or alkylnaphthalenes, chlorinated aromatics and chlorinated aliphatic hydrocarbons such as chlorobenzenes, chlorethylenes or methylene chloride, aliphatic hydrocarbons such as cyclohexane or paraffins, for example petroleum fractions, mineral and vegetable oils, alcohols such as butanol or glycol and their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar Solvents such as dimethylformamide and dimethyl sulfoxide, and water.
  • aromatics such as xylene, toluene, or alkylnaphthalenes
  • chlorinated aromatics and chlorinated aliphatic hydrocarbons such as chlorobenzenes,
  • Possible solid carriers are: e.g. Ammonium salts and natural rock powders such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and synthetic rock powders such as highly disperse silica, aluminum oxide and silicates are suitable as solid carriers for granules: e.g. broken and fractionated natural rocks such as calcite, marble, pumice, sepiolite, dolomite and synthetic granules from inorganic and organic flours as well as granules from organic material such as sawdust, coconut shells, corn cobs and tobacco stems; as emulsifying and / or foaming agents are possible: e.g.
  • nonionic and anionic emulsifiers such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, e.g. Alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates and protein hydrolyzates;
  • Possible dispersants are: e.g. Lignin sulfite liquor and methyl cellulose.
  • Adhesives such as carboxymethyl cellulose, natural and synthetic powdery, granular or latex-shaped polymers, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, and natural phospholipids such as cephalins and lecithins and synthetic phospholipids can be used in the formulations.
  • Other additives can be mineral and vegetable oils.
  • Dyes such as inorganic pigments, e.g. Iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin, azo and metal phthalocyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc can be used.
  • the formulations generally contain between 0.1 and 95 percent by weight of active compound, preferably between 0.5 and 90%.
  • the active compounds according to the invention can also be used in a mixture with known herbicides and / or with substances which improve crop tolerance (“safeners”) for weed control, finished formulations or tank mixes being possible Mixtures with weed control compositions which contain one or more known herbicides and a safener are also possible.
  • safeners substances which improve crop tolerance
  • herbicides are suitable for the mixtures, for example Acetochlor, Acifluorfen (-sodium), Aclonifen, Alachlor, Alloxydim (-sodium), Ametryne, Ami- carbazone, Amidochlor, Amidosulfuron, Anilofos, Asulam, Atrazine, Azafenidin, Azimsulfuron, Beflubutamide, Benazolin (-ethyl), Benulfureson -methyl), bentazone, benzfendizone, benzobicyclone, benzofenap, benzoylprop (-ethyl), bialaphos, bifenox, bispyribac (-sodium), bromobutide, bromofenoxim, bromoxynil, butachlor, butafenacil (-allyl), butroxydim, butylate, cafenimole, cafenimole Carbetamides, Carfentrazone (-ethoxy
  • a mixture with other known active compounds such as fungicides, insecticides, acaricides, nematicides, bird repellants, plant nutrients and agents which improve soil structure, is also possible.
  • the active substances or combinations of active substances can be used as such, in the form of their formulations or in the use forms prepared therefrom by further dilution, such as ready-to-use solutions, suspensions, emulsions, powders, pastes and granules. They are used in the usual way, e.g. by pouring, spraying, spraying, sprinkling.
  • the active substances or combinations of active substances according to the invention can be applied both before and after emergence of the plants. They can also be worked into the soil before sowing.
  • the amount of active ingredient used can vary over a wide range. It essentially depends on the type of effect desired. In general, the application rates are between 1 g and 10 kg of active ingredient per hectare of soil, preferably between 5 g and 5 kg per ha.
  • 1 part by weight of active compound of the formula (I) comprises 0.001 to 1000 parts by weight, preferably 0.01 to 100 parts by weight, particularly preferably 0.05 to 20 parts by weight, of one of the compounds mentioned above under (b ') which improves the tolerance of the crop plants (antidotes / safeners).
  • the active substance combinations according to the invention are generally used in the form of ready-to-use formulations.
  • the active ingredients contained in the active ingredient combinations can also be mixed in individual formulations during use, i.e. be used in the form of tank mixes.
  • mineral-compatible plant-based ingredients for example the commercial preparation "Rako Binol" or ammonium salts such as ammonium sulfate or ammonium rhodanide.
  • the new active ingredient combinations can be used as such, in the form of their formulations or in the use forms prepared therefrom by further dilution, such as ready-to-use solutions, suspensions, emulsions, powders, pastes and granules. They are used in the usual way, e.g. by pouring, spraying, spraying, dusting or scattering.
  • the application rates of the active compound combinations according to the invention can be varied within a certain range; they hang among other things depending on the weather and soil factors.
  • the application rates are between 0.001 and 5 kg per ha, preferably between 0.005 and 2 kg per ha, particularly preferably between 0.01 and 0.5 kg per ha.
  • the active compound combinations according to the invention can be applied before and after emergence of the plants, that is to say in the pre-emergence and post-emergence process.
  • the safeners to be used according to the invention can be used for pretreating the seed of the cultivated plant (dressing the seeds) or introduced into the seed furrows before sowing or used separately before the herbicide or together with the herbicide before or after emergence of the plants become.
  • reaction solution is poured onto 750 ml of ice-cold 20% HCl, extracted with MTB ether, the combined organic phases are washed with 20% HCl, dried and evaporated in vacuo at room temperature. Yield: 72 g (94% of theory).
  • the crude product (80%) is used without further workup to prepare the ester of the formula XTX-1.
  • Emulsifier 2 parts by weight of alkylaryl polyglycol ether
  • active compound 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier and the concentrate is diluted to the desired concentration with water containing emulsifier.
  • Cabbage leaves (Brassica oleracea), which are heavily infested with the green parsley aphid (Myzus persicae), are treated by immersing them in the active ingredient preparation of the desired concentration.
  • the kill is determined in%. 100% means that all aphids have been killed; 0% means that no aphids have been killed.
  • Emulsifier 2 parts by weight of alkylaryl polyglycol ether
  • active compound 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier and the concentrate is diluted to the desired concentration with water containing emulsifier.
  • Bean plants Phaseolus vulga s
  • Tetranychus urticae which are heavily infested with all stages of the common spider mite (Tetranychus urticae)
  • an active ingredient preparation of the desired concentration is immersed in an active ingredient preparation of the desired concentration.
  • the effect is determined in%. 100% means that all spider mites have been killed; 0% means that no spider mites have been killed.
  • Emulsifier 2 parts by weight of alkylaryl polyglycol ether
  • active compound 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier and the concentrate is diluted to the desired concentration with water containing emulsifier.
  • Cotton leaves which are heavily infested with the cotton aphid (Aphis gossypii), are treated by dipping into the active ingredient preparation of the desired concentration.
  • the kill is determined in%. 100% means that all aphids have been killed; 0% means that no aphids have been killed.
  • Active ingredients Active ingredient killing degree concentration in ppm in% after 6 "
  • Solvent 7 parts by weight of dimethylformamide emulsifier: 2 parts by weight of alkylaryl polyglycol ether
  • active compound 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier and the concentrate is diluted with water to the desired concentration.
  • Vessels are filled with sand, active ingredient solution, Meloidogyne incognita egg larva suspension and lettuce seeds.
  • the lettuce seeds germinate and the plantlets develop.
  • the galls develop at the roots.
  • the nematicidal effect is determined in% using the formation of bile. 100% means that no galls were found; 0% means that the number of galls on the treated plants corresponds to that of the untreated control.
  • Solvent 78 parts by weight of acetone, 1.5 parts by weight of dimethylformamide emulsifier: 0.5 part by weight of alkylaryl polyglycol ether
  • active compound 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier and the concentrate is diluted to the desired concentration with water containing emulsifier.
  • Chinese cabbage leaf slices (Brassica pekinensis), which are affected by all stages of the green peach aphid (Myzus persicae), are sprayed with an active ingredient preparation of the desired concentration.
  • the effect is determined in%. 100% means that all aphids have been killed; 0% means that no aphids have been killed.
  • Emulsifier 2 parts by weight of alkylaryl polyglycol ether
  • active compound 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier and the concentrate is diluted to the desired concentration with water containing emulsifier.
  • Cabbage leaves (Brassica oleracea) are treated by being dipped into the preparation of active compound of the desired concentration and populated with larvae of the horseradish leaf beetle (Phaedon cochleariae) while the leaves are still moist.
  • the kill is determined in%. 100% means that all beetle larvae have been killed; 0% means that none of the beetle larvae have been killed.
  • Solvent 78 parts by weight of acetone, 1.5 parts by weight of dimethylformamide emulsifier: 0.5 part by weight of alkylaryl polyglycol ether
  • active compound 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier and the concentrate is diluted to the desired concentration with water containing emulsifier.
  • Chinese cabbage leaf slices (Brassica pekinensis) are sprayed with an active ingredient preparation of the desired concentration and, after drying, are populated with larvae of the horseradish leaf beetle (Phaedon cochleariae).
  • the effect is determined in%. 100% means that all beetle larvae have been killed; 0% means that no beetle larvae have been killed.
  • Emulsifier 2 parts by weight of alkylaryl polyglycol ether
  • active compound 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier and the concentrate is diluted to the desired concentration with water containing emulsifier.
  • Bean plants Phaseolus vulgaris
  • Tetranychus urticae which are heavily infested with all stages of the common spider mite (Tetranychus urticae), are immersed in an active ingredient preparation of the desired concentration.
  • the effect is determined in%. 100% means that all spider mites have been killed; 0% means that no spider mites have been killed.
  • Solvent 78 parts by weight of acetone, 1.5 parts by weight of dimethylformamide emulsifier: 0.5 part by weight of alkylaryl polyglycol ether
  • active compound 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier and the concentrate is diluted to the desired concentration with water containing emulsifier.
  • Bean leaf slices Phaseolus vulgaris
  • Triticae Tricholine dexase
  • Bean leaf slices Phaseolus vulgaris
  • which are affected by all stages of the common spider mite Tetranychus urticae
  • an active ingredient preparation of the desired concentration is sprayed with an active ingredient preparation of the desired concentration.
  • the effect is determined in%. 100% means that all spider mites have been killed; 0% means that no spider mites have been killed.
  • Emulsifier 1 part by weight of alkylaryl polyglycol ether
  • active compound 1 part by weight of active compound is mixed with the stated amount of solvent, the stated amount of emulsifier is added and the concentrate is diluted with water to the desired concentration.
  • Test plants with a height of 5 to 15 cm are sprayed with the active substance preparation in such a way that the desired amounts of active substance are applied per unit area.
  • the concentration of the spray liquor is chosen so that the desired amounts of active compound are applied in 1000 l of water / ha.
  • the degree of damage to the plants is rated in% damage compared to the development of the untreated control.
  • Emulsifier 1 part by weight of alkylaryl polyglycol ether
  • active compound 1 part by weight of active compound is mixed with the stated amount of solvent, the stated amount of emulsifier is added and the concentrate is diluted with water to the desired concentration.
  • Seeds of the test plants are sown in normal soil. After about 24 hours, the soil is sprayed with the active ingredient preparation in such a way that the desired amounts of active ingredient are applied per unit area.
  • the concentration of the spray liquor is chosen so that the desired amounts of active compound are applied in 1000 l of water / ha.
  • the degree of damage to the plants is rated in% damage compared to the development of the untreated control.
  • Test compounds formulated in the form of wettable powders (WP) are then applied as an aqueous suspension with a water application rate equivalent to 600 1 ha with the addition of 0.2% wetting agent in different dosages to the surface of the covering earth.
  • Seeds of monocotyledonous or dicotyledonous weed or cultivated plants are laid out in wood fiber pots in sandy loam soil, covered with soil and grown in the greenhouse under good growth conditions.
  • the test plants are treated at the single-leaf stage 2-3 weeks after sowing.
  • the test compounds formulated as wettable powder (WP) are sprayed onto the green parts of the plant in various dosages with a water application rate of the equivalent of 600 l / ha with the addition of 0.2% wetting agent.
  • WP wettable powder
  • Test plants are laid out in wood fiber pots or in plastic pots in sandy loam soil, covered with soil and grown in the greenhouse, during the growing season also outdoors outside the greenhouse, under good growth conditions. Two to three weeks after sowing, the test plants are treated in one to three leaf stages.
  • the test compounds formulated as wettable powder (WP) or liquid (EC) are sprayed onto the plants and the soil surface in various dosages with a water application rate of the equivalent of 3001 / ha with the addition of wetting agent (0.2 to 0.3%).
  • WP wettable powder
  • EC liquid
  • Seeds of the crop plants are treated with the safener substance before sowing (indication of the amount of safener in percent based on the seed weight) - crop plants are sprayed with the safener with a certain amount of hectare before use of the test substances (usually 1 day before use of the test substances)
  • the safener is applied together with the test substance as a tank mixture (indication of the safener amount in g / ha or as a ratio to the herbicide).
  • the effect of the safener can be assessed by comparing the effect of test substances on crops which have been treated with and without safener.
  • Test insect Diabrotica balteata - larvae in the soil
  • Emulsifier 1 part by weight of alkylaryl polyglycol ether
  • active compound 1 part by weight of active compound is mixed with the stated amount of solvent, the stated amount of emulsifier is added and the concentrate is diluted with water to the desired concentration.
  • the active ingredient preparation is poured onto the floor.
  • the concentration of the active ingredient in the preparation is practically irrelevant, the only decisive factor is the amount of active ingredient per unit volume of soil, which is given in ppm (mg / 1). You fill the bottom in 0.25 1 pots and let them stand at 20 ° C.
  • Emulsifier 1 part by weight of alkylaryl polyglycol ether
  • active compound 1 part by weight of active compound is mixed with the stated amount of solvent and the stated amount of emulsifier, and the concentrate is diluted with water to the desired concentration.

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  • Life Sciences & Earth Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Environmental Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Plant Pathology (AREA)
  • Pest Control & Pesticides (AREA)
  • Agronomy & Crop Science (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Indole Compounds (AREA)

Abstract

L'invention concerne de nouveaux dérivés d'acide tétramique spirocycliques substitués par 2-halogéno-6-alkylphényle, de formule (I), dans laquelle A, B, G, X, Y et Z ont la signification indiquée dans la description. Elle concerne également plusieurs procédés et des produits intermédiaires pour la production de ces nouveaux composés, ainsi que l'utilisation de ces derniers comme pesticides et/ou herbicides. Elle concerne en outre des herbicides sélectifs qui contiennent d'une part lesdits dérivés d'acide tétramique spirocycliques substitués par 2-halogéno-6-alkylphényle, de formule (I), et d'autre part au moins un composé améliorant la compatibilité desdits dérivés avec les plantes cultivées.
EP04797575A 2003-11-05 2004-11-04 Derives d'acide tetramique spirocycliques substitues par 2-halogeno-6-alkylphenyle Withdrawn EP1697321A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE10351646A DE10351646A1 (de) 2003-11-05 2003-11-05 2-Halogen-6-alkyl-phenyl substituierte spirocyclische Tetramsäure-Derivate
PCT/EP2004/012443 WO2005044796A1 (fr) 2003-11-05 2004-11-04 Derives d'acide tetramique spirocycliques substitues par 2-halogeno-6-alkylphenyle

Publications (1)

Publication Number Publication Date
EP1697321A1 true EP1697321A1 (fr) 2006-09-06

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Application Number Title Priority Date Filing Date
EP04797575A Withdrawn EP1697321A1 (fr) 2003-11-05 2004-11-04 Derives d'acide tetramique spirocycliques substitues par 2-halogeno-6-alkylphenyle

Country Status (9)

Country Link
US (1) US20070129252A1 (fr)
EP (1) EP1697321A1 (fr)
CN (1) CN1874997A (fr)
AR (1) AR046614A1 (fr)
AU (1) AU2004287596A1 (fr)
BR (1) BRPI0416267A (fr)
CA (1) CA2544537A1 (fr)
DE (1) DE10351646A1 (fr)
WO (1) WO2005044796A1 (fr)

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EP3938348A1 (fr) 2019-03-15 2022-01-19 Bayer Aktiengesellschaft Nouvelles 3-(2-brome-4-alkinyl-6-alkoxyphényl)-3-pyrroline-2-ones et leur utilisation comme herbicides
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US20070129252A1 (en) 2007-06-07
BRPI0416267A (pt) 2007-01-09
CN1874997A (zh) 2006-12-06
CA2544537A1 (fr) 2005-05-19
AU2004287596A1 (en) 2005-05-19
WO2005044796A1 (fr) 2005-05-19
AR046614A1 (es) 2005-12-14
DE10351646A1 (de) 2005-06-09

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