EP1682501A2 - 2-halogen-6-alkyl-phenyl-substituierte tetramsäure-derivate - Google Patents

2-halogen-6-alkyl-phenyl-substituierte tetramsäure-derivate

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Publication number
EP1682501A2
EP1682501A2 EP04803102A EP04803102A EP1682501A2 EP 1682501 A2 EP1682501 A2 EP 1682501A2 EP 04803102 A EP04803102 A EP 04803102A EP 04803102 A EP04803102 A EP 04803102A EP 1682501 A2 EP1682501 A2 EP 1682501A2
Authority
EP
European Patent Office
Prior art keywords
alkyl
alkoxy
optionally
formula
halogen
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP04803102A
Other languages
German (de)
English (en)
French (fr)
Inventor
Reiner Fischer
Stefan Lehr
Dieter Feucht
Peter Lösel
Olga Malsam
Guido Bojack
Thomas Auler
Martin Jeffrey Hills
Heinz Kehne
Christopher Hugh Rosinger
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Bayer CropScience AG
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Bayer CropScience AG
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Filing date
Publication date
Application filed by Bayer CropScience AG filed Critical Bayer CropScience AG
Publication of EP1682501A2 publication Critical patent/EP1682501A2/de
Withdrawn legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
    • C07D207/34—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two 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
    • C07D207/36—Oxygen or sulfur atoms
    • C07D207/38—2-Pyrrolones
    • 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
    • A01N43/90—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
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C233/45—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups
    • C07C233/46—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
    • C07C233/47—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom having the carbon atom of the carboxamide group bound to a hydrogen atom or to a carbon atom of an acyclic saturated carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D207/10—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
    • C07D207/16—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
    • C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
    • C07D495/04—Ortho-condensed systems

Definitions

  • the invention relates to new 2-halogen-6-alkyl-phenyl-substituted tetramic acid derivatives, several processes and intermediates for their preparation and their use as pesticides and / or herbicides.
  • the invention also relates to new selective herbicidal active compound combinations which contain 2-halogen-6-alkyl-phenyl-substituted spirocyclic tetramic acid.
  • EP-A-0262 399 and GB-A-2266 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-pyrrolidine-2,4-dione derivatives EP-A-355 599 and EP-A-415 211) and substituted monocyclic 3-aryl-pyrrolidine-2 are known with herbicidal, insecticidal or acaricidal activity , 4-dione derivatives (EP-A-377 893 and EP-A-442077).
  • EP-A-442 073 Polycyclic 3-arylpyrrolidine-2,4-dione derivatives (EP-A-442 073) and 1H-arylpyrrolidine-dione derivatives (EP-A ⁇ 156063, EP-A-521 334, EP-A-596298) are also known , EP-A-613 884, EP-A-
  • Y represents alkyl
  • D represents hydrogen or an optionally substituted radical from the series
  • Alkyl alkenyl, alkynyl, alkoxyalkyl, alkylthioalkyl or optionally substituted cycloalkyl
  • a and D together with the atoms to which they are attached for a saturated or unsaturated and optionally at least one heteroatom contained in the A, D part of the unsubstituted or substituted cycle,
  • E represents a metal ion equivalent or an ammonium ion
  • L represents oxygen or sulfur
  • M oxygen or sulfur
  • R 1 for optionally substituted alkyl, alkenyl, alkoxyalkyl, alkylthioalkyl or polyalkoxyalkyl or for cycloalkyl or heterocyclyl optionally substituted by halogen, alkyl or alkoxy or for optionally substituted phenyl, phenylalkyl, phenylalkenyl or hetaryl,
  • R 2 for alkyl, alkenyl, alkoxyalkyl or polyalkoxyalkyl optionally substituted by halogen or for cycloalkyl, phenyl or benzyl optionally substituted in each case,
  • R 3 , R 4 and R 5 independently of one another each for alkyl, alkoxy, alkylamino, dialkylamino, alkylthio, alkenylthio or optionally substituted by halogen
  • R 6 and R 7 independently of one another for hydrogen, each for optionally by
  • N atom to which they are attached form an optionally substituted cycle which may contain oxygen or sulfur,
  • D represents hydrogen or an optionally substituted radical from the series
  • a and D together with the atoms to which they are attached, for a saturated or unsaturated and optionally containing at least one heteroatom, in the A, D part unsubstituted or substituted cycle.
  • the compounds of the formula (I) can be present in different compositions as geometric and or optical isomers or isomer mixtures, which can optionally be separated in a customary manner.
  • A, B, D, 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, D, X, Y and Z have the meanings given above,
  • R 8 represents alkyl (preferably CC 6 alkyl)
  • R 1 has the meaning given above and
  • R 1 has the meaning given above
  • R 2 and M have the meanings given above,
  • 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
  • R 2 has the meaning given above and
  • R 3 has the meaning given above
  • R 4 and R 5 have the meanings given above and
  • Me for a mono- or divalent metal preferably an alkali or alkaline earth metal such as lithium, sodium, potassium, magnesium or calcium
  • an alkali or alkaline earth metal such as lithium, sodium, potassium, magnesium or calcium
  • R 10 , R ⁇ , R 12 independently of one another represent hydrogen or alkyl (preferably Cj-C 8 -alkyl),
  • R 6 and L have the meanings given above,
  • the new compounds of the formula (I) have very good activity as pesticides, preferably as insecticides and / or acaricides and / or as herbicides.
  • (b 1 ) at least one compound from the following group of compounds which improves the tolerance of crop plants:
  • EP-A-269806 and EP-A-333131 also related compounds in EP-A-269806 and EP-A-333131), 5- (2,4-dichlorobenzyl) -2-isoxazoline-3-carboxylic acid ethyl ester, 5-phenyl-2-isoxazoline-3-carboxylic acid -ethyl ester, 5- (4-fluorophenyl) -5-phenyl-2-isoxazoline-3-carboxylic acid ethyl ester (cf.
  • n a number 0, 1, 2, 3, 4 or 5
  • a 1 represents one of the divalent heterocyclic groupings outlined below,
  • n stands for a number 0, 1, 2, 3, 4 or 5
  • a 2 represents optionally substituted by C 1 -C 4 -alkyl and / or C 1 -C 4 alkoxy-carbonyl and / or C r C 4 - alkenyloxy-carbonyl-substituted alkanediyl having 1 or 2 carbon atoms,
  • R 14 represents hydroxy, mercapto, amino, C r C 6 alkoxy, CC 6 alkylthio, C 1 -C 6 alkylamino or di (C 4 C 4 alkyl) amino
  • R 15 for hydroxy, mercapto, amino, -C-C 7 alkoxy, CC 6 -alkenyloxy, C r C 6 -alkenyloxy-C C 6 -alkoxy, -C-C 6 -alkylthio, CC 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, each optionally substituted by fluorine, chlorine and / or bromine -
  • R 18 represents hydrogen, in each case optionally substituted by fluorine, chlorine and / or bromine - C 6 alkyl, C 2 -C 6 alkenyl or C 2 -C 6 alkynyl, - alkoxy-C-alkyl, dioxolanyl-C C 4 - alkyl, furyl, furyl -CC-C 4 alkyl, thienyl, thiazolyl, piperidinyl, or phenyl optionally substituted by fluorine, chlorine and / or bromine or CrC 4 alkyl, R 17 and R 18 together also represent each optionally C 3 -C 6 substituted by C 1 -C 4 alkyl, phenyl, furyl, a fused benzene ring or by two substituents which, together with the C atom to which they are attached, form a 5- or 6-membered carboxy cycle -Alkanediyl or C 2 -C 5 -oxaalkanediy
  • R 19 represents hydrogen, cyano, halogen, or C 1 -C 6 -alkyl, C 3 -C 6 -cycloalkyl or phenyl which are each 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 CC 6 alkyl, C 3 -C 6 cycloalkyl or tri- (C 4 -C 4 alkyl) silyl,
  • R 21 represents hydrogen, cyano, halogen, or each -Gt-alkyl, C 3 -C6-cycloalkyl or phenyl which is optionally substituted by fluorine, chlorine and / or bromine,
  • X 1 represents nitro, cyano, halogen, CrGralkyl, CC -haloalkyl, CC 4 -alkoxy or CC 4 -haloalkoxy,
  • X 2 represents hydrogen, cyano, nitro, halogen, C 1 -C 4 -alkyl, C r C 4 -haloalkyl, CC 4 -alkoxy or C] -C 4 -haloalkoxy,
  • X 3 represents hydrogen, cyano, nitro, halogen, alkyl CC, Cr haloalkyl, C r C 4 alkoxy or C ⁇ -C is 4 haloalkoxy,
  • R 22 represents hydrogen or -CC 4 alkyl
  • R 23 represents hydrogen or -CC 4 alkyl
  • R 2 for hydrogen, each optionally substituted by cyano, halogen or CC 4 alkoxy -Cg-alkyl, C r C 6 -alkoxy, CC 6 -alkylthio, -C-C 6 -alkylamino or di- (CC 4 -alkyl) - a ino, or in each case optionally substituted by cyano, halogen or -CC 4 alkyl C 3 -C 6 cycloalkyl, C 3 -C 6 cycloalkyloxy, C 3 -C 6 cycloalkylthio or C 3 -C 6 - (- cloalkylamino stands,
  • R 25 represents hydrogen, optionally cyano-, hydroxyl-, halogen or CC 4 -alkoxy-substituted C r C 6 alkyl substituted in each case optionally cyano- or halogen-C, 3 - C 6 alkenyl or C 3 -C 6 -alkynyl, or optionally C 3 -C 6 cycloalkyl substituted by cyano, halogen or CC alkyl,
  • R 26 for hydrogen, optionally substituted by cyano, hydroxy, halogen or CC 4 alkoxy -CC 6 alkyl, in each case optionally substituted by cyano or halogen, C 3 - C 6 alkenyl or C 3 -C 6 -alkynyl, optionally cyano-, halogen or C ⁇ -C 4 -alkyl-substituted C 3 -C 6 cycloalkyl, or optionally substituted by nitro, cyano, halo, C ⁇ -C alkyl, CC 4 -Halogenalkyl, CC 4 -alkoxy or C] -C 4 -Halogenalkoxy substituted phenyl, or together with R 25 for C 2 -C 6 -alkanediyl or C 2 -C 5 - optionally substituted by -CC 4 -alkyl in each case Oxaalkanediyl stands,
  • X 4 represents nitro, cyano, carboxy, carbamoyl, formyl, sulfamoyl, hydroxy, amino, halogen, - C 4 alkyl, CC 4 haloalkyl, -Gralkoxy or C r C 4 haloalkoxy, and
  • X 5 represents nitro, cyano, carboxy, carbamoyl, formyl, sulfamoyl, hydroxy, amino, halogen, - C 4 alkyl, Cr haloalkyl, -C 4 alkoxy or CC haloalkoxy.
  • the compounds according to the invention are generally defined by the formula (I). preferred
  • X preferably represents chlorine or bromine
  • Y preferably represents C j -C 3 alkyl
  • Z preferably represents ethyl, n-propyl or n-butyl
  • G preferably represents hydrogen (a)
  • A is preferred for hydrogen, C 2 -C 6 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 6 -alkoxy-C 1 -C 4 -alkyl or for optionally up to three times by halogen, C 1 -C 4 -alkyl or C 1 -C4-
  • B preferably represents hydrogen, C j -CG alkyl or C j -CG-alkoxy-C ⁇ -C 4 alkyl,
  • D preferably for hydrogen, for in each case optionally mono- to trisubstituted by halogen C, -C 8 -alkyl, QC 8 -alkenyl, C 1 -C 6 -alkoxy-C 2 -C 4 -alkyl or CC 6 -alkylthio-C 2 -C 4 alkyl, for optionally single to triple by halogen, CC 4 alkyl, dC 4 -
  • a and D together preferably for a C 3 -C 6 -alkanediyl or C 3 -C 5 -alkenediyl group, in each of which a methylene group is optionally replaced by oxygen or sulfur and which are each optionally mono- to disubstituted by halogen, hydroxy, CC 4 -alkyl or ⁇ -alkoxy, or by another -Cg-alkanediyl, C 3 -C 6 -alkenediyl or -Cö-alkanedienediyl group which forms a fused-on ring
  • E represents a metal ion equivalent or an ammonium ion
  • L represents oxygen or sulfur
  • M oxygen or sulfur
  • R 1 preferably for each, optionally up to seven times, by halogen, simple to
  • R 2 preferably represents - in each case monosubstituted to trisubstituted by halogen - C 20 -alkyl, -C 20 -alkenyl, - -alkoxy- -Qralkyl or poly-C r C 6 -alkoxy-C 2 -C 6 -alkyl,
  • C 3 -C 8 cycloalkyl which is optionally mono- to disubstituted by halogen, C r C 6 -alkyl or C t -C ⁇ -alkoxy or
  • R 3 preferably for -Cs-alkyl which is optionally mono- to polysubstituted by halogen or for in each case optionally monosubstituted or twice by halogen, -Ce-alkyl, -C 6 -alkoxy, -C-C -haloalkyl, C] -C 4 -haloalkoxy, Cyano or nitro substituted phenyl or benzyl,
  • R 4 and R 5 independently of one another, are preferred for in each case one to three times
  • R 6 and R 7 independently of one another preferably represent hydrogen, represent in each case optionally monosubstituted to trisubstituted by halogen CC 8 alkyl, C 3 -C 8 cycloalkyl, C ⁇ -C 8 alkoxy, C 3 -C 8 - alkenyl or C Cs-Alkoxy- -Cg-alkyl, for each optionally monosubstituted to trisubstituted by halogen, -CC 8 -alkyl, C] -C 8 -haloalkyl or -Cg-alkoxy or phenyl or benzyl together for an optionally monosubstituted to twice by C1-C4
  • Rl3 is preferred for C 1 - which is optionally monosubstituted to trisubstituted by halogen.
  • Rl 3 ' preferably for hydrogen, C ⁇ -Cg-alkyl or C3 -Cg-alkenyl
  • B preferably for hydrogen, -CC 6 -alkyl or CC 4 -alkoxy -CC-C 2 alkyl
  • D is preferred for hydrogen, for CC 8 -alkyl which is optionally monosubstituted to trisubstituted by halogen, C, -C 8 -alkenyl, C r C 6 -alkoxy-C 2 -C 4 -alkyl or CC 6 -alkylthio-C 2- C 4 alkyl, for C 3 -C 8 cycloalkyl which is optionally monosubstituted to trisubstituted by halogen, C 1 -C 4 alkyl, CC 4 alkoxy or C 1 -C 2 haloalkyl,
  • a and D together preferably represent a C 3 -C ö -alkanediyl or C 3 -C 6 -alkenediyl group which in each case optionally one Methylengrappe is replaced by oxygen or sulfur and which are in each case optionally monosubstituted to disubstituted by halogen,
  • 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
  • G particularly preferably represents hydrogen (a), then stands
  • C ⁇ -C 3 alkyl or is optionally monosubstituted to disubstituted by fluorine, chlorine, C ⁇ -C alkyl or C ⁇ -C 2 alkoxy-substituted C 3 -C 6 cycloalkyl, B particularly preferably for hydrogen, C -C 2 -alkyl or C -C 4 -alkoxy-C ⁇ -C 2 -alkyl,
  • D is also particularly preferred for in each case optionally up to three times by fluorine or
  • A only represents hydrogen or C 3 -C 3 -alkyl
  • a and D together are particularly preferred for a C 3 -C 5 alkanediyl group, in which a methylene group is optionally replaced by oxygen or sulfur and which is optionally monosubstituted or disubstituted by -C alkyl or CC 2 alkoxy,
  • a and D together with the atoms to which they are attached represent one of the groups AD-1 to AD-10
  • G is particularly preferred for one of the groups
  • E represents a metal ion equivalent or an ammonium ion
  • L represents oxygen or sulfur
  • M oxygen or sulfur
  • pyrazolyl for pyrazolyl, thiazolyl, pyridyl, pyrimidyl, furanyl or thienyl, each of which is optionally mono- to disubstituted by fluorine, chlorine, bromine or C 1 -C 2 -alkyl,
  • R 2 particularly preferably represents in each case optionally mono- to trisubstituted by fluorine or chlorine, C ⁇ C 0 alkyl, C 2 -C ⁇ 0 alkenyl, C ⁇ -C 4 -alkoxy -C 4 -alkyl or poly-C C - alkoxy-C 2 -C 4 alkyl,
  • phenyl or benzyl which is optionally mono- to disubstituted by fluorine, chlorine, bromine, cyano, nitro, --C 4 -alkyl, methoxy, trifluoromethyl or trifluoromethoxy,
  • R 3 is particularly preferably for CC 4 -alkyl which is optionally monosubstituted to trisubstituted by fluorine or chlorine or for phenyl which is substituted in each case optionally by fluorine, chlorine, bromine, CC-alkyl, C r C 4 -alkoxy, trifluoromethyl, trifluoromethoxy, cyano or nitro or benzyl,
  • R 4 and R 5 independently of one another, are particularly preferred for C 1 -C 6 -alkyl, CC 6 -alkoxy, CC 6 - which is optionally mono- to trisubstituted by fluorine or chlorine -
  • R and R 7 independently of one another are particularly preferably hydrogen, for in each case optionally mono- to trisubstituted by fluorine or chlorine -CC 6 alkyl, C 3 -C 6 cycloalkyl, Q- C 4 alkoxy, C 3 -C 6 - Alkenyl or C r C 6 alkoxy-C 2 -C 6 alkyl, for phenyl which is optionally mono- to disubstituted by fluorine, chlorine, bromine, trifluoromethyl, C r C 4 -alkyl or CC 4 -alkoxy, or together for one optionally monosubstituted to doubly methyl-substituted Cs-C ⁇ -alkylene, in which a methylene group is optionally present
  • R 3 particularly preferably represents C ⁇ -C 4 alkyl, C 3 -C 4 alkenyl, C 3 -C 4 alkynyl or C ⁇ -C 4 -alkoxy-C 2 - C alkyl, or C 3 -C 4 cycloalkyl, in which may have replaced a methylene group with oxygen,
  • B particularly preferably for hydrogen, -CC 4 -alkyl or - -alkoxy- -Qralkyl
  • D is also particularly preferred for in each case optionally up to three times by fluorine or
  • a and D together are particularly preferred for a C 3 -C 5 alkanediyl group, in which a methylene group is optionally replaced by oxygen or sulfur and which is optionally monosubstituted or disubstituted by C 1 -C 2 -alkyl or C 1 -C 2 alkoxy,
  • a and D together with the atoms to which they are attached represent one of the groups AD-1 to AD-10
  • 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
  • G very particularly preferably represents hydrogen (a), then stands
  • B very particularly preferably for hydrogen, methyl or ethyl
  • D very particularly preferably for hydrogen
  • D also very particularly preferably for methyl, ethyl, n-propyl, iso-propyl, n-butyl, sec-butyl, iso-butyl, cyclopropyl, cyclopentyl or cyclohexyl, with the proviso that then
  • a and D together very particularly preferably for a C 3 -C 4 -alkanediyl group, in which in each case one methylene group is optionally replaced by oxygen or sulfur and which is optionally mono- to disubstituted by methyl
  • M oxygen or sulfur
  • R 1 very particularly preferably for in each case optionally up to three times by fluorine or
  • furanyl, thienyl or pyridyl each optionally substituted by chlorine, bromine or methyl
  • R 2 very particularly preferably for CC 8 alkyl, C 2 -C 6 alkenyl or C Cs-alkoxy-Qr -alkyl,
  • R 3 very particularly preferably for -Gralkyl optionally monosubstituted to trisubstituted by fluorine or chlorine or for in each case optionally monosubstituted by fluorine, chlorine, bromine, C 1 -C 4 -alkyl, C 1 -C 4 alkoxy, trifluoromethyl, trifluoromethoxy, cyano or nitro substituted phenyl or benzyl,
  • R 6 very particularly preferably for hydrogen, for CC 4 -alkyl, C 3 -C 6 -cycloalkyl or allyl, for phenyl which is optionally simply substituted by fluorine, chlorine, bromine, methyl, methoxy or trifluoromethyl,
  • R "and R ' are very particularly preferably for a C 5 -C 6 alkylene radical in which a methylene group is optionally replaced by oxygen,
  • B very particularly preferably for hydrogen, methyl or ethyl
  • D also very particularly preferably for methyl, ethyl, n-propyl, iso-propyl, n-butyl, sec-butyl, iso-butyl, cyclopropyl, cyclopentyl or cyclohexyl, with the proviso that then
  • Y stands in particular for methyl
  • G in particular represents hydrogen (a), then stands
  • R 1 in particular for CC 6 -alkyl or C 1 -C 2 -alkoxy-C r C 2 -alkyl which is optionally mono- to trisubstituted by fluorine or chlorine,
  • R 2 in particular for Ci-Cs-alkyl
  • R 3 in particular for CC 4 alkyl
  • AD-1 The general definitions or explanations of residues or explanations listed above or in preferred areas can be combined with one another, that is to say also between the respective areas and preferred areas. They apply accordingly to the end products as well as to the preliminary and intermediate products.
  • 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 (Ha), (üb), (He), (LTd) and (He) are as follows Are defined.
  • n 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 in each case methylene or ethylene which is optionally substituted by methyl, ethyl, methoxycarbonyl or 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,
  • 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-
  • 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
  • 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, Ethoxymethyl, methoxyethyl, ethoxyethyl, dioxolanylmethyl,
  • 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 through hydroxy, cyano, fluorine, chlorine,
  • Methoxy, ethoxy, n- or i-propoxy substituted 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, chlorodifluoromethyl , 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-
  • 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 preferably represents the numbers 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 through cyano, fluorine, chlorine, methoxy,
  • 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 26 preferably represents hydrogen, in each case optionally through cyano, hydroxy, fluorine, chlorine,
  • X 4 preferably represents nitro, cyano, carboxy, carbamoyl, formyl, sulfamoyl, hydroxy, amino,
  • 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.
  • 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- l 1 most preferred, with Cloquintocet-mexyl and Mefenpyr-diethyl being particularly emphasized.
  • Table 7 examples of the selectively herbicidal combinations according to the invention, each of an active ingredient of the formula (I) and in each case one of the safeners defined above, are listed in Table 7 below.
  • the compounds of the general formula (He) to be used as safeners according to the invention are known and / or can be prepared by compounds known per se (cf. WO-A-99/66795 / US-A-6251 827). It has now surprisingly been found that the active substance combinations defined above of substituted cyclic ketoenols of the general formula (I) and safeners (antidots) from component (b ') listed above have a particularly high herbicidal activity and are available in various forms, with very good crop plant tolerance Cultures, especially in cereals (especially wheat), but also in soy, potatoes, corn and rice can be used for selective weed control.
  • component (b ') in particular with regard to the protection of cereal plants, such as e.g. Wheat, barley and rye, but also maize and rice, as crops.
  • A, B, D, 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, D, X, Y and Z have the meanings given above,
  • A, B, D, 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 phosphopentachloride
  • 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
  • X, Y and Z have the meaning given above, first with alcoholates (e.g. alkali metal alcoholates such as sodium methylate or sodium ethylate) in the presence of a diluent (e.g. alcohol derived from the alcoholate) at temperatures between 0 ° C and 150 ° C, preferably between 20 ° C and 120 ° C, and then with an acid (preferably an inorganic acid such as sulfuric acid) at temperatures between -20 ° C and 150 ° C, preferably 0 ° C and 100 ° C.
  • 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
  • R 13 represents alkyl, preferably C 1 -C 6 -alkyl
  • the compounds of formula (XXI) are new and can be prepared by processes which are generally known in principle.
  • the compounds of formula (XXH) are known compounds of organic chemistry. Copper (H) chloride and vinylidene chloride have long been known and can be bought.
  • A, B, D, X, Y, Z and R 8 have the meanings given above, if aminonitriles of the formula (XXHT),
  • A, B, D, X, Y and Z have the meanings given above,
  • Process (A) is characterized in that compounds of the formula (H), in which A, B, D, X, Y, Z and R 8 have the meanings given above, in the presence of a diluent and in the presence of a base subject to intramolecular condensation.
  • Diluents in process (A) according to the invention can all be compared to
  • Reactants inert organic solvents are used.
  • Hydrocarbons such as toluene and xylene
  • ethers such as dibutyl ether, tetrahydrofuran, dioxane, glycol dimethyl ether and diglycol dimethyl ether
  • polar solvents such as dimethyl sulfoxide, sulfolane, dimethylformamide and N-methylpyrrolidone
  • 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.
  • 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).
  • Carboxylic acid halides of the formula (hT) optionally in the presence of a diluent and optionally 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 also preferably usable
  • Halogenated hydrocarbons such as methylene chloride, chloroform, carbon tetrachloride, chlorobenzene and o-dichlorobenzene, in addition 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 and, such as dimethyl sulfone , 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 triemylamine, pyridine, diazabicyclooctane (DABCO), diazabicycloundecene (DBU), diazabicyclononene (DBN), Hunig base and N, N-dimethylaniline, and also alkaline earth metal oxides, such as magnesium oxide 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.
  • the 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.
  • the starting materials of the formula (I-a) and the carboxylic acid halide of the formula (HI) are generally in each case used in approximately equivalent amounts. However, it is also possible to use the carboxylic acid halide in a larger excess (up to 5 mol). The processing takes place according to usual methods.
  • Process (Bß) is characterized in that compounds of the formula (I-a) are each reacted with carboxylic anhydrides of the formula (IV), 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.
  • 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 (TV) 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.
  • Carboxylic anhydride and the resulting carboxylic acid removed by distillation or by washing with an organic solvent or with water.
  • Process (C) is characterized in that compounds of the formula (Ia) are reacted in each case with chloroformic acid esters or chloroformic acid thiol esters of the 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 carbonate, potassium carbonate, are preferably usable and calcium carbonate and alkali hydroxides such as sodium hydroxide and
  • 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 usable, furthermore halogenated hydrocarbons such as methylene chloride, chloroform, carbon tetrachloride,
  • Chlorobenzene and o-dichlorobenzene in addition ketones, such as acetone and methyl isopropyl ketone, further 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.
  • ketones such as acetone and methyl isopropyl ketone
  • further ethers such as diethyl ether, tetrahydrofuran and dioxane
  • carboxylic acid esters such as ethyl acetate
  • strongly polar solvents such as dimethyl sulfoxide and sulfolane.
  • the reaction temperature can be varied within a substantial range when carrying out process (C) according to the invention.
  • 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 chloroformate or chloroformate thiol ester 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 precipitated salts and to concentrate the remaining reaction mixture by stripping off the diluent.
  • Formula (Ia) each with (Da) compounds of formula (VI) in the presence of a diluent and optionally in the presence of an acid binder or (Dß) carbon disulfide and then with alkyl halides of the formula (VH) optionally in the presence of a diluent and optionally in the presence of a base implements.
  • 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 tertiary burylate 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 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, triethylamine, dibenzylamine, diisopropylethylamine, pyridine, quinoline, diazabicyclooctane (DABCO), diazabicyclonones (DBN) and
  • DBU Diazabicycloundecene
  • 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.
  • 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 in each case reacted with sulfonyl chlorides of the formula (VTH), 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 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, 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) is characterized in that compounds of the formula (Ia) are each reacted with phosphorus compounds of the formula (TX), if appropriate in the presence of a diluent and if appropriate in the presence of an acid binder.
  • TX phosphorus compounds of the formula
  • 1 mol of the compound (Ia), 1 to 2, preferably 1 to 1.3 mol of the phosphorus compound of the formula (LX) are employed at temperatures between -40 ° C. to obtain compounds of the formula (Ie) and 150 ° C, preferably between -10 and 110 ° C.
  • 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,
  • 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 the volatile
  • 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.
  • Suitable diluents 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 can be used.
  • the 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 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.
  • catalysts can be added to accelerate the reaction.
  • Organotin compounds such as e.g. Dibutyltin dilaurate can be used.
  • inert polar organic solvents such as ethers, esters, amides, sulfones, sulfoxides or halogenated hydrocarbons, are suitable as diluents, if appropriate.
  • the enolate salt of the compound (I-a) is prepared by adding strong deprotonating agents (such as sodium hydride or potassium tertiary butoxide), the further addition of acid binders can be dispensed with.
  • strong deprotonating agents such as sodium hydride or potassium tertiary butoxide
  • examples include 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 controlling 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.
  • Thysanura e.g. 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. Hercinothrips femoralis, Thrips tabaci, Thrips palmi, Frankliniella occidentalis.
  • Homoptera e.g. Aleurodes brassicae, Bemisia tabaci, Trialeurodes vaporariorum, Aphis gossypii, Brevicoryne brassicae, Cryptomyzus ribis,
  • Nilaparvata lugens Aonidiella aurantii, Aspidiotus hederae, Pseudococcus spp., Psylla spp. From the order of the Lepidoptera, for example, Pectinophora gossypiella, Bupalus piniarius, Cheimatobia brumata, Lithocolletis blancardella, Hyponomeuta padella, Plutella xylostella, Malacosoma neustria, Euproctis chrysorrhoea, Lymantria spp., Agristella sppber, Bucculisella syll ., Earias insulana, Heliothis spp., Mamestra brassicae, Panolis flammea, Spodoptera spp., Trichoplusia ni, Ca ⁇ ocapsa pomonella, Pieris spp., Chilo spp
  • Otiorrhynchus sulcatus Otiorrhynchus sulcatus, Cosmopolites sordidus, Ceuthorrhynchus assimilis, Hypera postica, Dermestes spp., Trogoderma spp., Anthrenus spp., Attagenus spp., Lyctus spp., Meligethes aeneus, Ptinus spp., Giptusibbium psol. Tenebrio molitor, Agriotes spp., Conoderus spp., Melolontha melolontha, Amphimallon solstitialis, Costelytra zealandica, Lissorhoptrus oryzophilus.
  • 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.
  • the plant parasitic nematodes include, for example, Pratylenchus spp., Radopholus similis, Ditylenchus dipsaci, Tylenchulus semipenetrans, Heterodera spp., Globodera spp., Meloidogyne spp., Aphelenchoides spp., Longidorus spp., Xiphinema spp., Trichodorus spp., Bursaphelenchus spp.
  • the compounds or active compound combinations according to the invention can, if appropriate, also be used as herbicides in certain concentrations or application rates. If appropriate, the compounds can also be used as intermediates or products for the synthesis of further active compounds.
  • plants and parts of plants can be treated.
  • Plants are understood here to mean all plants and plant populations, such as desired and undesirable wild plants or cultivated plants (including naturally occurring cultivated plants).
  • Cultivated plants can be plants that are grown by conventional breeding and
  • Plant parts are to be understood to mean all above-ground and underground parts and organs of plants, such as shoots, leaves, flowers and roots, examples being leaves,
  • the plant parts also include crops and vegetative and generative propagation material, for example cuttings, tubers, rhizomes, offshoots and seeds.
  • Active ingredient combinations are carried out directly or by influencing 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 prepared in a known manner, for example 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-forming agents. If water is used as an extender, organic solvents can, for example, also be used as auxiliary solvents.
  • 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-forming agents.
  • organic solvents can, for example, also be used as auxiliary 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, 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.
  • Ammonium salts and natural rock flours such as kaolins, clays, talc, chalk,
  • Quartz, attapulgite, montmorillonite or diatomaceous earth and synthetic rock flour, 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. non-ionic 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 sulfate leaching and methyl cellulose.
  • Adhesives such as carboxymethyl cellulose, natural and synthetic polymers in the form of powders, granules or latices, such as rubber 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% 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 fungicides, bactericides, acaricides, nematicides or insecticides, in order, for example, to broaden the spectrum of activity or to prevent the development of resistance. In many cases, synergistic effects are obtained, ie the effectiveness of the mixture is greater than the effectiveness of the individual components.
  • Debacarb dichlorophene, diclobutrazole, diclofluanide, diclomezin, dicloran, diethofencarb, difenoconazole, dimethirimol, dimethomo ⁇ h, diniconazole, diniconazole-M, dinocap, diphenylamine,
  • Famoxadon Fenapanil, Fenarimol, Fenbuconazol, Fenfuram, Fenitropan, Fenpiclonil, Fenpropidin, Fenpropimo ⁇ h, Fentinacetat, Fentinhydroxyd, Ferbam, Ferimzon, Fluazinam, Flumetover, Fluoromid, Fluquinconazol, Flu ⁇ rimidol, Flilrilidol, Flilrilidol, Flilrilidol, Flilrilidol, Flilrilidol, Flilrilidol, Flilrilidol, Flolrilidol,
  • hnazalil imibenconazole, iminoctadine, hninoctadineal besilate, iminoctadinetriacetate, iodocarb,
  • IBP iprobefos
  • Kasugamycin, Kresoxim-methyl, copper preparations such as: copper hydroxide, copper naphthenate, copper oxychloride, copper sulfate, copper oxide, oxine-copper and Bordeaux mixture, Mancopper, Mancozeb, Maneb, Meferimzone, Mepanipyrim, Mepronil, Metalaxyl, Metconazol, Methasulfocarb, Methfuroxam, Metiram, Metomeclam, Metsulfovax, Mildiomycin, Myclobutanil, Myclozolin,
  • Oxadixyl Oxamocarb, Oxolinicacid, Oxycarboxim, Oxyfenthiin,
  • Tebuconazole Tebuconazole, tecloftalam, tecnazene, Tetcyclacis, tetraconazole, thiabendazole, Thicyofen, Thifluzamide, thiophanate-methyl, thiram, Tioxymid, tolclofos-methyl, tolylfluanid, triadimefon, triadimenol, Triazbutil, triazoxide, Trichlamid, tricyclazole, Tridemo ⁇ h, trifloxystrobin, triflumizole, triforine, triticonazole,
  • Azinphos A Azinphos M, Azocyclotin,
  • Chlorethoxyfos Chlorfenapyr, Chlorfenvinphos, Chlorfluazuron, Chlormephos, Chlo ⁇ yrifos,
  • Cloethocarb Clofentezine ,. Clothianidine, cyanophos, cycloprehe, cycloprothrin, cyfluthrin,
  • Fenamiphos Fenazaquin, Fenbutatin oxide, Fenitrothion, Fenothiocarb, Fenoxacrim, Fenoxycarb, Fenpropathrin, Fenpyrad, Fenpyrithrin, Fenpyroximate, Fenvalerate, Fipronil, Fluazinam, Fluazuron, Flubrocythrinate, Flucycloxoxinon, Flutoxinoxin, Fluutinoxin, Fluutinoxin, , Fosthiäzate, Fubfenprox, Furathiocarb, 5 Granuloseviruses
  • Halofenozide HCH, Heptenophos, Hexaflumuron, Hexythiazox, Hydroprene,
  • Thiacloprid Thiamethoxam, Thiaprönil, Thiatriphos, Thiocyclam hydrogen oxalate, Thiodicarb, Thiofanox, Thuringiensin, Tralocythrin, Tralomethrin, Triarathene, Triazamate, Triazophos, Triazuron, Trichlophenidine, Trichlarbonon, Trichlarbonuron
  • the active compounds according to the invention can also 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 combinations of active ingredients is distinguished by an excellent residual action on wood and clay and by a good stability to alkali on limed substrates.
  • plants and their parts can be treated.
  • plant species and plant varieties and their parts occurring wildly or obtained by conventional organic breeding methods, such as crossing or protoplast fusion, are treated.
  • transgenic plants and plant cultivars which have been obtained by genetic engineering methods, if appropriate in combination with conventional methods (Gehetic Modified Organisms) and their parts are treated.
  • Plants of the plant varieties which are in each case commercially available or in use are particularly preferably treated according to the invention.
  • Plant cultivars are understood to mean plants with new properties (“traits”) which have been grown both by conventional breeding, by mutagenesis or by recombinant DNA techniques. This can be varieties, organic and
  • Plant species or plant cultivars their location and growth conditions (soils, climate, growing season, nutrition) can also have superadditive (“synergistic") effects due to the treatment according to the invention.
  • superadditive for example, reduced application rates and / or widening of the spectrum of activity and / or an increase in the effect 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 harvest products, higher storability and / or processability of the harvested products, 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 have received genetic material through the genetic engineering modification 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, acceleration of 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. Further and particularly highlighted examples of such properties are one. increased defense of the plants against animal and microbial pests, such as against insects, mites, phytopathogenic fungi, bacteria and / or viruses, and an increased tolerance of the plants to certain herbicidal active ingredients.
  • transgenic plants are the important crop 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), corn , 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), CryllA, CryHIA, 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 which are particularly emphasized are the increased tolerance of the plants to certain herbicidal active compounds, for example imidazolinones, sulfo ⁇ ylureas, glyphosate or phosphinotricin (for example “PAT” gene).
  • the genes imparting the desired properties can also occur in combinations with one another in the transgenic plants.
  • Examples of "Bt plants” are maize varieties, cotton varieties, soy varieties and potato varieties that are marketed under the trade names YIELD GARD® (e.g. corn, cotton, soy), KnockOut® (e.g.
  • herbicide-tolerant plants are corn varieties, cotton varieties and soy varieties that are marketed under the trade names Roundup Ready® (tolerance to glyphosate e.g. corn, cotton, soy), Liberty Link® (tolerance to phosphinotricin, e.g. rapeseed), IMI® (tolerance to Imidazolinone) and STS® (tolerance to sulfonylureas such as maize).
  • the herbicide-resistant plants (conventionally bred to herbicide tolerance) include the varieties sold under the name Clearf ⁇ eld® (e.g. 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 two Active ingredients or mixtures of the preferred ranges given above 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.
  • Nematocerinä and Brachycerina e.g. Aedes spp., Anopheles spp., Culex spp., Simulium spp., Eusimulium spp., Phlebotomus spp., Lutzomyia spp., Culicoides spp., Chrysops spp., Hybomitra spp., Atylotus spp., Tabanus spp., Haematöpota spp ., Philipqmyia spp., Braula spp., Musca spp., Hydrotaea spp., Stomoxys spp., Haematobia spp., Morellia spp., Fannia spp., Glossina spp., Calliphora spp., Glossina spp., Chrysomyia s
  • Siphonaptrida e.g. Pulex spp., Ctenocephalides spp., Xenopsylla spp., Ceratophyllus spp.
  • Actinedida Prostigmata
  • Acaridida Acaridida
  • Acarapis spp. Cheyletiella spp., Omithocheyletia spp., Myobia spp., Psorergates spp., Demodex spp., Trombicula spp., Listrophorus spp., Acarus spp. Tyrophagus spp., Caloglyphus spp., Hypodectes.
  • the active substances or combinations of active substances according to the invention are also suitable for combating arthropods which are used in agricultural animals, 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 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.
  • the active substances or combinations of active substances according to the invention are used in a known manner by enteral administration in the form of, for example, tablets, capsules, drinkers, drenches, granules, pastes, boluses, the feed-through method, suppositories, by parenteral administration, such as for example by injections (intramuscular, subcutaneous, intravenous, intraperitoneal, etc.), implants, by 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, dusting, and with the help of drug-containing Formgro ⁇ ern, such as collars, ear tags, 'tail marks, limb bands, halters, marking devices, etc.
  • parenteral administration such as for example by injections (intramuscular, subcutaneous, intravenous, intraperitoneal, etc.), implants, by nasal application, by dermal application in the form of, for example, diving or bathing (
  • 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 to
  • insects may be mentioned by way of example and preferably, but without limitation:
  • Kalotermes flavicoUis Cryptotermes brevis, Heterotermes indicola, Reticulitermes flavipes, Reticulitermes santonensis, Reticulitermes lucifugus, Mastotermes darwiniensis, Zooterm ⁇ psis nevadensis, Coptotermes formosanus.
  • Bristle tails such as Lepisma saccharina.
  • non-living materials such as preferably plastics, adhesives, glues, papers and cartons, leather, wood, wood processing products and paints.
  • the material to be protected against 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:
  • Lumber Wooden beams, railway sleepers, bridge parts, jetties, wooden vehicles, boxes,
  • the active substances or combinations of active substances can be used as such, in the form of concentrates or generally customary formulas, 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 others
  • 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.
  • 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, are used as such low-volatility, water-insoluble, oily and oily solvents
  • Mineral oils with a boiling range of 170 to 220 ° C are advantageous.
  • 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 monochlomophthalene, preferably ⁇ -monochlomaphthalene, 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 or an aliphatic polar organic chemical solvent or solvent mixture is replaced.
  • hydroxyl and / or ester and / or Aliphatic organic chemical solvents containing ether groups such as, for example, glycol ethers, esters or the like, are 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, e.g. Polyvinyl acetate, polyester resin, polycondensation or polyaddition resin, polyurethane resin, alkyd resin or modified alkyd resin, phenolic resin, hydrocarbon resin such as lhden-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, e.g. Polyvinyl acetate, polyester resin, polycondensation or polyaddition resin, polyurethane resin, alkyd resin or modified alkyd resin, phenolic resin, hydrocarbon
  • 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.
  • All or part of the binder mentioned can be a fixing agent (mixture) or a
  • Plasticizer mixture to be replaced. These additives are intended to prevent volatilization of the active substances 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 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 by 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 such as chlo ⁇ yriphos, phoxim, silafluof ⁇ n, alphamethrin, cyfluthrin, cypermethrin, deltamethrin, permethrin, imidacloprid, NI-25, flufenoxuron, hexaflumuron, transfluthrin, methoxyphenophen, thiaphenuronoprid, as a particularly preferred mixing partner
  • fungicides such as epoxyconazole, hexaconazole, azaconazole, propiconazole, tebuconazole, cyproconazole, metconazole, hnazalil, dichlorofluoride, tolylfluanid, 3-iodo-2-propynylbutylcarbamate, N-octyl-isothiazolin-3-one and 4,5 octylisothiazolin-3-one.
  • the compounds or combinations of active substances according to the invention can be used to protect objects, in particular hulls, sieves, nets, structures,
  • Cirripedia (barnacles) are of particular importance.
  • Active ingredients can be based on the use of heavy metals such as in bis (trialkyltin) sulfide, tri- butyltin laurate, tri- / z-butyltin chloride, copper (I) oxide, triethyltin chloride, tri - »- butyl (2-phenyl- 4-chl ⁇ henoxy) tin, tributyltin oxide, molybdenum disulfide, antimony oxide, polymeric butyl titanate, phenyl (bispyridine) bismuth chloride, tri-n-butyltin fluoride, manganese ethylene bishio carbamate, zinc dimethyldithiocarbamate and copper amide zincamine, zinc ethylene bischloride, zinc ethylenebisthi
  • the ready-to-use antifouling paints may optionally contain other active ingredients, preferably algicides, fungicides, herbicides, muusicicides or other antifouling active ingredients.
  • Suitable combination partners for the antifouling agents according to the invention are preferably:
  • Benzo [6] thiophenecarboxylic acid cyclohexylamide-S, S-dioxide, dichlofluanid, fluorfolpet, 3-iodo-2-propynyl-butylcarbamate, tolylfluanid and azoles such as
  • 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 of 0.01 to 20% by weight.
  • the antifouling agents according to the invention further contain the usual ingredients such as in Ungerer, Chem. Ind. 1985, 37, 730-732 and Williams, Antifouling Marine Coatings, Noyes,
  • antifouling paints contain in particular binders.
  • binders examples include 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
  • 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. Also in
  • Self-polishing antifouling systems can incorporate the compounds according to the invention or the mixtures mentioned above.
  • 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 for example Argas persicus, Argas reflexus, Bryobia ssp., Dermanyssus gallinae, Glyciphagus domesticus, Omithodorus moubat, Rhipicephalus sanguineus, Trombicula alfireddugesi, Neutiombicula autumnalis, Dermatophagoides pteronissimus, Dermatophagoides forinae.
  • Opiliones e.g. Pseudosco ⁇ iones chelifer, Pseudosco ⁇ iones cheiridium, Opiliones phalangium.
  • Tinea cloacella Tinea pellionella
  • Tineola bisselliella From the order of the Siphonaptera, for example 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.
  • Heteroptera e.g. Cime hemipterus, Cimex lectularius, Rhodinus prolixus, Triatoma infestans.
  • the active substances or combinations of active substances 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:
  • Sphenoclea Stellaria, Taraxacum, Thlaspi, Trifolium, Urtica, Veronica, Viola, Xanthium.
  • Echinochloa Eleocharis, Eleusine, Eragrostis, Eriochloa, Festuca, Fimbristylis, Heteranthera, Imperata, Ischaemum, Leptochloa, Lolium, Monochoria, Panicum, Paspalum, Phalaris, Phleum, Poa, Rottboellia, Sagittaria Set, Sorgi, Sorgi.
  • 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
  • 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 weed control can be used in annual crops.
  • the compounds or active ingredient combinations 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 monocotyledon and dicotyledon weeds in monocotyledon and dicotyledon 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, solvent Liche powders, granules, suspension emulsion concentrates, active ingredient-impregnated natural and synthetic substances as well as fine encapsulation in polymeric substances.
  • 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, if appropriate using surface-active agents, ie 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.
  • Possible solid carriers are: e.g. Ammonium salts and natural rock flour, such as
  • Kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and synthetic rock powder, 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.
  • 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
  • Adhesives such as carboxymethyl cellulose, natural and synthetic powdery, granular or latex-shaped polymers are used, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, and natural phospholipids such as cephalins and lecithins and synthetic phospholipids.
  • Other additives can be mineral and vegetable oils.
  • Dyes such as inorganic pigments, for example 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 as a mixture with known herbicides and or with substances which improve crop tolerance (“safenem”) for weed control, ready formulations or tank mixes being possible mixtures with weed control compositions which contain one or more known herbicides and a safener are also possible.
  • safenem crop tolerance
  • Metobromuron (alpha-) Metolachlor, Metosulam, Metoxuron, Metribuzin, Metsulfuron (-methyl), Molinate, Monolinuron, Naproanilide, Napropamide, Neburon, Nicosulfuron, Norflurazon, Orbencarb, Oryzalin, Oxadiargyl, Oxomonononone, Oxadonononone, Oxadononone, Oxygenadiazon Oxyfluorfen, paraquat, pelargonic acid, pendimethalin, pendralin, pentoxazone, phenmedipham, picolinafen, pinoxaden, piperophos, pretilachlor, primisulfuron (- methyl), profluazole, prömetryn, propachlor, propanil, propaquizafop, propisochloro (propoxycarbons, Propyzamides, prosulfocarb, prosulfuron, pyraflufen (-ethy
  • Sulfentrazone Sulfomeruron (-methyl), Sulfosate, Sulfosulfuron, Tebutam, Tebuthiuron, Tepraloxydim, Terbuthylazine, Terbutryn, Thenylchlor, Thiafluamide, Thiazopyr, Thidiazimin, Thifensulfonon (-methyl), Thioben, Sulfuralkon, Sulfate, Alkaloxydililoxililazilazil, Carboxalimid Tribenuron (- methyl), triclopyr, tridiphane, trifluralin, trifloxysulfuron, triflusulfuron (-methyl), tritosulfuron.
  • 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.
  • active substances or combinations of active substances as such in the form of their formulations or the use forms prepared therefrom by further dilution, such as ready-to-use
  • Solutions, suspensions, emulsions, powders, pastes and granules are used. 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. Ini generally are their cost "amounts between 1 g and 10 kg of active compound per hectare of soil surface, preferably between 5 g and 5 kg per ha.
  • the advantageous effect of the tolerance of cultivated plants of the active compound combinations according to the invention is particularly pronounced at certain concentration ratios.
  • the weight ratios of the active ingredients in the active ingredient combinations can be varied within relatively large ranges.
  • 1 part by weight of active ingredient of the formula (I) 0.001. up 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 (antidots / safener).
  • the active compound combinations according to the invention are generally used in the form of finished formulations.
  • the contained in the active ingredient combinations are generally used in the form of finished formulations.
  • Active ingredients can also be mixed in individual formulations during use, i.e. be used in the form of tank mixes.
  • ammonium sulfate or ammonium rhodanide include 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 the pretreatment of the seed of the cultivated plant (dressing the seeds) or before sowing into the seed furrows. introduced or used separately before • the herbicide or used together with the herbicide before or after the plants have run off.

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  • 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)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Pyrrole Compounds (AREA)
EP04803102A 2003-11-05 2004-11-04 2-halogen-6-alkyl-phenyl-substituierte tetramsäure-derivate Withdrawn EP1682501A2 (de)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE10351647A DE10351647A1 (de) 2003-11-05 2003-11-05 2-Halogen-6-alkyl-phenyl substituierte Tetramsäure-Derivate
PCT/EP2004/012444 WO2005044791A2 (de) 2003-11-05 2004-11-04 2-halogen-6-alkyl-phenyl-substituierte tetramsäure-derivate

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EP (1) EP1682501A2 (ru)
JP (1) JP2007511476A (ru)
KR (1) KR20060100437A (ru)
CN (1) CN100562515C (ru)
AR (1) AR046925A1 (ru)
AU (1) AU2004287597A1 (ru)
BR (1) BRPI0415738A (ru)
CA (1) CA2544548A1 (ru)
DE (1) DE10351647A1 (ru)
EA (1) EA200600631A1 (ru)
IL (1) IL175349A0 (ru)
MX (1) MXPA06004854A (ru)
UA (1) UA86391C2 (ru)
WO (1) WO2005044791A2 (ru)
ZA (1) ZA200603505B (ru)

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UA86391C2 (ru) 2009-04-27
EA200600631A1 (ru) 2006-08-25
BRPI0415738A (pt) 2006-12-19
AR046925A1 (es) 2006-01-04
US20070225170A1 (en) 2007-09-27
CA2544548A1 (en) 2005-05-19
DE10351647A1 (de) 2005-06-09
WO2005044791A3 (de) 2005-08-11
IL175349A0 (en) 2006-09-05
MXPA06004854A (es) 2006-06-27
CN100562515C (zh) 2009-11-25
JP2007511476A (ja) 2007-05-10
ZA200603505B (en) 2007-07-25
WO2005044791A2 (de) 2005-05-19
CN1874995A (zh) 2006-12-06
AU2004287597A1 (en) 2005-05-19
KR20060100437A (ko) 2006-09-20

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