EP1181267A1 - Composes halogene - Google Patents

Composes halogene

Info

Publication number
EP1181267A1
EP1181267A1 EP00931134A EP00931134A EP1181267A1 EP 1181267 A1 EP1181267 A1 EP 1181267A1 EP 00931134 A EP00931134 A EP 00931134A EP 00931134 A EP00931134 A EP 00931134A EP 1181267 A1 EP1181267 A1 EP 1181267A1
Authority
EP
European Patent Office
Prior art keywords
formula
compounds
halogen
carbon atoms
alkyl
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Withdrawn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
EP00931134A
Other languages
German (de)
English (en)
Inventor
Dieter Arlt
Martin Hendrix
Hans-Ludwig Elbe
Gerd Hänssler
Karl-Heinz Kuck
Christoph Erdelen
Haruko Sawada
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
Original Assignee
Bayer AG
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Bayer AG filed Critical Bayer AG
Publication of EP1181267A1 publication Critical patent/EP1181267A1/fr
Withdrawn legal-status Critical Current

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    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/36—Radicals substituted by singly-bound nitrogen atoms
    • C07D213/40—Acylated substituent nitrogen atom
    • 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
    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/06—Unsaturated carboxylic acids or thio analogues thereof; Derivatives thereof
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof
    • A01N37/22—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof the nitrogen atom being directly attached to an aromatic ring system, e.g. anilides
    • 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
    • C07C233/12—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 halogen atoms or by nitro or nitroso groups
    • C07C233/13—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 halogen atoms or by nitro or nitroso groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
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    • C07C233/12—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 halogen atoms or by nitro or nitroso groups
    • C07C233/14—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 halogen atoms or by nitro or nitroso groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a ring other than a six-membered aromatic ring
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    • 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
    • C07C233/12—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 halogen atoms or by nitro or nitroso groups
    • C07C233/15—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 halogen atoms or by nitro or nitroso groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a six-membered aromatic ring
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    • C07C233/16—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 singly-bound oxygen atoms
    • C07C233/17—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 singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
    • C07C233/22—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 singly-bound oxygen atoms 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 an acyclic carbon atom of a carbon skeleton containing six-membered aromatic rings
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    • 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
    • C07C233/51—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 an acyclic carbon atom of a carbon skeleton containing six-membered aromatic rings
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    • 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
    • C07C233/53—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 a carbon atom of a six-membered aromatic ring
    • C07C233/55—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 a carbon atom of a six-membered aromatic ring having the carbon atom of the carboxamide group bound to a carbon atom of an unsaturated carbon skeleton
    • C—CHEMISTRY; METALLURGY
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    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C239/00—Compounds containing nitrogen-to-halogen bonds; Hydroxylamino compounds or ethers or esters thereof
    • C07C239/08—Hydroxylamino compounds or their ethers or esters
    • C07C239/10—Hydroxylamino compounds or their ethers or esters having nitrogen atoms of hydroxylamino groups further bound to carbon atoms of unsubstituted hydrocarbon radicals or of hydrocarbon radicals substituted by halogen atoms or by nitro or nitroso groups
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    • C07C239/00—Compounds containing nitrogen-to-halogen bonds; Hydroxylamino compounds or ethers or esters thereof
    • C07C239/08—Hydroxylamino compounds or their ethers or esters
    • C07C239/12—Hydroxylamino compounds or their ethers or esters having nitrogen atoms of hydroxylamino groups further bound to carbon atoms of hydrocarbon radicals substituted by singly-bound oxygen atoms
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    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
    • C07C251/32—Oximes
    • C07C251/62—Oximes having oxygen atoms of oxyimino groups esterified
    • C07C251/64—Oximes having oxygen atoms of oxyimino groups esterified by carboxylic acids
    • C07C251/66—Oximes having oxygen atoms of oxyimino groups esterified by carboxylic acids with the esterifying carboxyl groups bound to hydrogen atoms, to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
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    • C07C255/00—Carboxylic acid nitriles
    • C07C255/49—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
    • C07C255/58—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing cyano groups and singly-bound nitrogen atoms, not being further bound to other hetero atoms, bound to the carbon skeleton
    • C07C255/60—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing cyano groups and singly-bound nitrogen atoms, not being further bound to other hetero atoms, bound to the carbon skeleton at least one of the singly-bound nitrogen atoms being acylated
    • C—CHEMISTRY; METALLURGY
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    • C07C259/00—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups
    • C07C259/04—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups without replacement of the other oxygen atom of the carboxyl group, e.g. hydroxamic acids
    • C07C259/06—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups without replacement of the other oxygen atom of the carboxyl group, e.g. hydroxamic acids having carbon atoms of hydroxamic groups bound to hydrogen atoms or to acyclic carbon atoms
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    • C07C259/00—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups
    • C07C259/04—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups without replacement of the other oxygen atom of the carboxyl group, e.g. hydroxamic acids
    • C07C259/10—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups without replacement of the other oxygen atom of the carboxyl group, e.g. hydroxamic acids having carbon atoms of hydroxamic groups bound to carbon atoms of six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
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    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
    • C07C57/52—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing halogen
    • C07C57/58—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing halogen containing six-membered aromatic rings
    • C07C57/60—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing halogen containing six-membered aromatic rings having unsaturation outside the rings
    • C—CHEMISTRY; METALLURGY
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    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/62—Halogen-containing esters
    • C07C69/65—Halogen-containing esters of unsaturated acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
    • C07D213/61—Halogen atoms or nitro radicals
    • C—CHEMISTRY; METALLURGY
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    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
    • C07D213/72—Nitrogen atoms
    • C07D213/75—Amino or imino radicals, acylated by carboxylic or carbonic acids, or by sulfur or nitrogen analogues thereof, e.g. carbamates
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    • C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
    • C07D217/12—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with radicals, substituted by hetero atoms, attached to carbon atoms of the nitrogen-containing ring
    • C07D217/18—Aralkyl radicals
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    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
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    • C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D277/22—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
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    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
    • C07D295/18—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
    • C07D295/182—Radicals derived from carboxylic acids
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    • C07C2601/14—The ring being saturated

Definitions

  • the invention relates to new halogen compounds, a process for their preparation and their use for the treatment of plants against attack by phytopathogenic microorganisms and insects.
  • the invention further relates to new intermediates and processes for their production.
  • R.1 represents substituted or unsubstituted aryl- or heteroaryl
  • R.2 for hydrogen, substituted or unsubstituted alkyl, aryl or
  • Heteroaryl is, with halogen, alkoxy and aryloxy radicals as substituents on the alkyl radicals, and substituents on the aryl or hetaryl radical
  • NO 2 are possible X * and ⁇ 2 are the same or different and are independently fluorine, chlorine or bromine,
  • X ⁇ represents hydrogen, fluorine, chlorine or bromine
  • N represents optionally substituted nitrogen-bonded heterocyclyl or a group -E-A-R ⁇ , in which
  • R 3 I w is where R J is alkyl
  • R ⁇ stands for hydrogen, or for optionally substituted aryl, cycloalkyl or heterocyclyl.
  • the saturated or unsaturated hydrocarbon chains such as alkyl, alkanediyl, alkenyl or alkynyl, also in combination with heteroatoms, such as in alkoxy, alkyl thio or alkylamino, are each straight-chain or branched, in particular 1 to 6 carbon atoms. If an alkyl or alkanediyl chain is interrupted by more than one heteroatom, these can be the same or different. If an alkyl or alkanediyl chain is interrupted by more than one oxygen atom, two oxygen atoms are not directly adjacent.
  • Halogen generally represents fluorine, chlorine, bromine or iodine, preferably fluorine, chlorine or bromine, in particular fluorine or chlorine.
  • Haloalkyl stands for partially or completely halogenated alkyl with in particular 1 to 6 carbon atoms and 1 to 13 identical or different
  • Halogen atoms In the case of polyhalogenated haloalkyl, the halogen atoms can be the same or different. Preferred halogen atoms are fluorine and chlorine and especially fluorine. If the haloalkyl carries further substituents, the maximum possible number of halogen atoms is reduced to the remaining free valences.
  • Aryl stands for aromatic, mono- or polycyclic hydrocarbon rings, e.g. Phenyl, naphthyl, anthryl, phenanthryl, preferably phenyl or naphthyl, especially phenyl.
  • Heteroaryl stands for mono- or polycyclic heteroaryl compounds, preferably with 5 to 6 ring members, such as e.g. Thienyl, pyridyl or thiazole.
  • Heterocyclyl stands for saturated or unsaturated, as well as aromatic, ring-shaped compounds in which at least one ring member has a hetero atom, i.e. H. one of
  • Carbon is different atom. If the ring contains several heteroatoms, these can be the same or different. Heteroatoms are preferably oxygen, nitrogen or sulfur. If the ring contains several oxygen atoms, they are not adjacent. If appropriate, the ring-shaped compounds together with other carbocyclic or heterocyclic, fused or bridged rings together form a polycyclic ring system. A polycyclic ring system can be linked via the heterocyclic ring or a fused-on carbocyclic ring. Mono- or bicyclic ring systems are preferred, in particular mono- or bicyclic aromatic ring systems. It was further found that the new halogen compounds of the general formula (I) are obtained (process a) if carboxylic acid halides of the formula (II)
  • R, R ⁇ , X 1, ⁇ 2 and X- ⁇ have the meanings given above and
  • ⁇ 4 represents halogen
  • the compounds according to the invention can optionally be in the form of mixtures of various possible isomeric forms, in particular stereoisomers, such as e.g.
  • E and Z, or optical isomers are present. Both the E and the Z isomers, the individual enantiomers, the racemates, as well as any mixtures of these isomers, are claimed.
  • the present application preferably relates to halogen compounds of the formula (I) in which
  • R represents optionally mono- to tetrasubstituted phenyl, naphthyl or heteroaryl with 5 to 6 ring members, the possible substituents preferably being selected from the list below:
  • Hydroximinoalkyl or alkoximinoalkyl each having 1 to 6 carbon atoms in the individual alkyl parts;
  • R ⁇ stands for hydrogen, or for optionally mono- to tetrasubstituted phenyl, naphthyl or heteroaryl with 5 to 6 ring members, the possible substituents preferably being selected from the list below:
  • ⁇ l and X ⁇ are the same or different and are independently fluorine, chlorine or bromine, and X ⁇ represents hydrogen, fluorine, chlorine or bromine, and
  • Y represents heterocyclyl with 3 to 6 ring members which is optionally monosubstituted to tetrasubstituted by alkyl having 1 to 4 carbon atoms or a group -E-A-R ⁇ , in which
  • I stands for R 3 for alkyl with 1-4 carbon atoms
  • R4 represents hydrogen, or optionally mono- to tetrasubstituted phenyl, isoquinolyl, naphthyl, heterocyclyl with 5 to 6 ring members or cycloalkyl with 3 to 7 carbon atoms, the possible substituents preferably being selected from the list below:
  • Phenyl, phenylthio or phenoxy Phenyl, phenylthio or phenoxy.
  • the present application relates in particular to compounds of the formula (I) in which
  • Rl represents phenyl, naphthyl, thienyl, pyridyl or thiazolyl which is optionally monosubstituted to tetrasubstituted, the possible substituents preferably being selected from the list below:
  • X * and X ⁇ are the same or different and are independently fluorine, chlorine or bromine, and
  • X- > represents hydrogen, fluorine, chlorine or bromine
  • R 3 I is where R is methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl,
  • R ⁇ stands for hydrogen, cyclohexyl, benzothiazolyl, cyclohexanothienyl, dioxoanyl or for optionally mono- to tetrasubstituted phenyl, isoquinolyl, naphthyl, thienyl, pyridyl or thiazolyl, the possible substituents preferably being selected from the list below:
  • Phenyl, phenylthio, phenoxy Phenyl, phenylthio, phenoxy.
  • X 1 represents chlorine.
  • X 2 represents chlorine
  • X 3 represents hydrogen.
  • R 1 represents 4-fluorophenyl, 4-bromophenyl, phenyl, 3-chlorophenyl, in particular 4-chlorophenyl.
  • R 2 represents hydrogen
  • radical definitions given in detail for these radicals in the respective combinations or preferred combinations of radicals are replaced as desired by radical definitions of others, irrespective of the respectively specified combination of the radicals.
  • esters such as ethyl 3- (4-chloro-phenyl) -5,5-dichloro-4-pentenoate, benzyl 3- (4-chlorophenyl) - 5,5-dichloro-4-pentenoate, 3- (2,6-dichloro-phenyl) - 3-methyl-5,5-dichloro-4-pentenoic acid and 3- (2,6-dichloro-pyridyl-4 -) - 5,5-dichloro-4-pentenoic acid methyl ester.
  • Amides of the pentenoic acids prepared by the process according to the invention can also be used as biologically active substances.
  • Examples include 3- (4-chloro-phenyl) -5,5-dichloro-4-pentenoic acid-N- (4-chlorophenyl) amide, 3- (4-chloro-phenyl) -5,5-dichloro-4-pentenoic acid-N- cyclohexyl amide, 3- (4-chloro-phenyl) -5,5-dichloro-4-pentenoic acid-N- ⁇ -phenethylamide, 3- (4-chloro-phenyl-5,5-dichloro-4-pentenoic acid-N- ⁇ -p -chloro-phenethylamide, 3- (4-chloro-phenyl) -5,5-dichloro-4-pentenoic acid-N- (3,5-dichloro-phenyl) -amide, 3- (2,6-dichloro-phenyl) -5.5 -dichloro-4-pentenoic acid-
  • N- ⁇ -p-methylphenethylamide 3- (4-chlorophenyl) -5,5-dichloro-4-pentenoic acid-N- (6-chloropyridyl-2) -amide, 3- (2,6-dichloro -pyridyl-4) -5,5-dichloro-4-pentenoic acid-N- (4- chl ⁇ henyl) -amide, and 3- (2-chloro-6-fluorophenyl) -5,5-dichloro-4-pentenoic acid -N-methyl-N- (4-chl ⁇ henyl) amide.
  • Formula (II) provides a general definition of the carboxylic acid halides required as starting materials for carrying out process a) according to the invention for the preparation of the compounds of the formula (I).
  • R, R2, ⁇ , X ⁇ and X ⁇ preferably or in particular have those meanings which have already been in connection with the description of the compounds of the invention
  • Formula (I) was given as preferred or as particularly preferred for R, R2, X 1 , ⁇ 2 and X ⁇ .
  • X ⁇ stands for halogen, especially chlorine.
  • nucleophiles of the formula (III) which are furthermore required as starting materials for carrying out the process a) according to the invention for the preparation of the compounds of the formula (I) are known synthetic chemicals.
  • the carboxylic acid halides of the formula (II) are not yet known; they are also the subject of the present application as new substances.
  • R, R ⁇ , X 1, ⁇ 2 and X ⁇ have the meanings given above,
  • halogenating agent by way of example and preferably phosgene, phosphorus trichloride, phosphorus tribromide, phosphopentachloride, phosphorus oxychloride, thionyl chloride or thionyl bromide, if appropriate in the presence of a diluent, for example and preferably dichloromethane, trichloroethane or chlorobenzene, and if appropriate in the presence of a catalyst, for example and preferably Pyridine or dimethylformamide.
  • a halogenating agent by way of example and preferably phosgene, phosphorus trichloride, phosphorus tribromide, phosphopentachloride, phosphorus oxychloride, thionyl chloride or thionyl bromide, if appropriate in the presence of a diluent, for example and preferably dichloromethane, trichloroethane or chlorobenzene, and if appropriate
  • Formula (IV) provides a general definition of the carboxylic acids required as starting materials for carrying out process b) according to the invention for the preparation of the compounds of the formula (II).
  • Rl, R2, ⁇ l, ⁇ 2 and X ⁇ preferably or in particular have those meanings which, in connection with the description of the compounds of the formula (I) according to the invention, are preferred or particularly preferred for R% R2 , ⁇ l, ⁇ 2 and X ⁇ were specified.
  • the carboxylic acids of the formula (IV) are not yet known, they are new substances and, as a subgroup of the compounds of the formula (I), are also the subject of the present application.
  • carboxylic acids of the formula (IV) also have a strong fungicidal and resistance-inducing action and can be used for the treatment of plant diseases.
  • Examples of compounds of the formula (IV) which do not limit the scope of the invention are:
  • R, R2, ⁇ l and ⁇ 2 have the meanings given above and
  • Z stands for a grouping which forms an acidic condition
  • Formula (V) provides a general definition of the dihaloethene derivatives required as starting materials for carrying out process c) according to the invention for the preparation of the carboxylic acids of the formula (IV).
  • R, R2, ⁇ and ⁇ preferably or in particular have those meanings which already in connection with the description of the compounds of the invention
  • Formula (I) were given as preferred or as particularly preferred for Rl, R, ⁇ l and ⁇ .
  • Z stands for a group which is split off under the reaction conditions, a cationic reactive intermediate being formed, which reacts electrophilically with the olefinic component (1,1-dichloroethane) to form a further reactive intermediate which is finally solvolysed.
  • Grouping Z are, for example, chlorine, bromine, hydroxy, alkoxy, preferably methoxy or ethoxy, or aryloxy, preferably phenoxy.
  • Strong acids which can be used as mediators of the synthesis reaction are, for example and preferably, sulfuric acid, methanesulfonic acid, trifluoroacetic acid or phosphoric acid. Sulfuric acid is particularly preferred, especially in the concentration range of 60-95%.
  • R, R2, ⁇ l and ⁇ 2 have the meanings given above,
  • aqueous base such as sodium hydroxide solution.
  • Formula (VI) provides a general definition of the trihaloethane derivatives required as starting materials for carrying out process d) according to the invention for the preparation of the trihalomethyl compounds of the formula (V).
  • Formula (VI) has R, R, ⁇ l and ⁇ preferably or in particular those meanings which have already been given in connection with the description of the compounds of the formula (I) as preferred or as particularly preferred for Rl, R2, Formell and ⁇ were.
  • ⁇ 5 represents halogen, preferably chlorine or bromine.
  • Z * also stands for halogen, preferably for
  • Chlorine or bromine Chlorine or bromine.
  • the compounds of formula VI are known and can be obtained by known methods (see e.g. Phosphorus Sulfur 19, 1984, 199-204).
  • R, R2, ⁇ and ⁇ 2 have the meanings given above, and
  • ⁇ 6 represents halogen
  • R 5 represents alkyl
  • a base preferably an alkaline earth metal or alkali metal hydroxide, such as, for example, lithium hydroxide, sodium hydroxide or potassium hydroxide, if appropriate in the presence of water and if appropriate in the presence of a further diluent, such as, for example, tetrahydrofuran, dimethoxyethane or dioxane.
  • a base preferably an alkaline earth metal or alkali metal hydroxide, such as, for example, lithium hydroxide, sodium hydroxide or potassium hydroxide, if appropriate in the presence of water and if appropriate in the presence of a further diluent, such as, for example, tetrahydrofuran, dimethoxyethane or dioxane.
  • Formula (VII) provides a general definition of the esters required to carry out process e) according to the invention for the preparation of the carboxylic acids of the formula (IV) with X ⁇ as halogen as starting materials.
  • Rl, R2, ⁇ l and ⁇ 2 preferably or in particular have those meanings which, in connection with the description of the compounds of the formula (I) according to the invention, are preferred or particularly preferred for Rl, R, ⁇ l and ⁇ were specified.
  • ⁇ 6 represents halogen, preferably fluorine, chlorine or bromine.
  • R- is alkyl, preferably methyl or ethyl.
  • the esters of formula (VII) are not yet known, they are new substances and, as a subgroup of the compounds of formula (I), are also the subject of the present application. They are obtained if halogen alkyl esters of the formula (VIII),
  • R, R, R5, ⁇ l ⁇ 2 and ⁇ ß have the meanings given above, and
  • X 7 represents halogen
  • a base preferably an alkaline earth metal or alkali metal hydride, or alcoholate, such as sodium hydride, sodium methylate, sodium ethylate or potassium tert-butoxide, optionally in the presence of a diluent, such as methanol, ethanol, tetrahydrofuran, dimethoxyethane, dioxane, dimethyl thylformamide or dimethyl sulfoxide.
  • a base preferably an alkaline earth metal or alkali metal hydride, or alcoholate, such as sodium hydride, sodium methylate, sodium ethylate or potassium tert-butoxide, optionally in the presence of a diluent, such as methanol, ethanol, tetrahydrofuran, dimethoxyethane, dioxane, dimethyl thylformamide or dimethyl sulfoxide.
  • haloalkyl esters required as starting materials for carrying out the process f) according to the invention for the preparation of the esters of the formula (VII) are generally defined by the formula (VIII).
  • R 1 , R 2 , R5, ⁇ l ⁇ 2 and ⁇ 6 preferably or in particular have those meanings which, in connection with the description of the compounds of the formula (VII) according to the invention, are preferred or particularly preferred for R. , R2, R5, ⁇ l ⁇ 2 and X "have been specified.
  • X 7 represents halogen, preferably fluorine, chlorine or bromine.
  • the haloalkyl esters of the formula (VIII) are not yet known; they are also the subject of the present application as new substances.
  • R, R2, R5 ⁇ l and ⁇ 2 have the meanings given above, with a conventional chlorination, bromination and iodination agent, such as, for example
  • halogen compounds required as starting materials for carrying out the process g) according to the invention for the preparation of the haloalkyl esters of the formula (VIII) are generally defined by the formula (I-a).
  • Rl, R2, R5, ⁇ l and ⁇ 2 preferably or in particular have those meanings which, in connection with the description of the compounds of the formula (VII) according to the invention, are preferred or particularly preferred for R, R, R5 ⁇ l and X were specified.
  • halogen compounds of the formula (I-a) are a subgroup of the compounds of the formula (I) according to the invention and can be obtained by process a).
  • Suitable diluents for carrying out process a) according to the invention are all inert organic solvents. These include, for example and preferably, aliphatic, alicyclic or aromatic carbon hydrogen, for example and preferably petroleum ether, hexane, heptane, cyclohexane, methylcyclohexane, benzene, toluene, xylene or decalin; halogenated hydrocarbons, such as, for example and preferably, chlorobenzene, dichlorobenzene, dichloromethane, chloroform, carbon tetrachloride, dichloroethane or trichloroethane; Ethers, for example and preferably diethyl ether, diisopropyl ether, methyl t-butyl ether,
  • Process a) according to the invention is optionally carried out in the presence of a suitable acid acceptor.
  • a suitable acid acceptor All conventional inorganic or organic bases are suitable as such. These preferably include alkaline earth metal or alkali metal hydroxides, acetates, carbonates or hydrogen carbonates, by way of example and with preference sodium hydroxide, potassium hydroxide, sodium acetate, potassium acetate,
  • Calcium acetate, sodium carbonate, potassium carbonate, potassium hydrogen carbonate or sodium hydrogen carbonate and tertiary amines for example and preferably trimethylamine, triethylamine, tributylamine, N, N-dimethylaniline, N, N-dimethylbenzylamine, pyridine, N-methylpiperidine, N-methylmo ⁇ holin, N, N-dimethylaminopyridine, diazabicyclooctane (DABCO), diazabicyclonones (DBN) or diazabicyclonecene (DBU).
  • DABCO diazabicyclooctane
  • DBN diazabicyclonones
  • DBU diazabicyclonecene
  • reaction temperatures can be varied within a substantial range when carrying out process a) according to the invention. In general, temperatures from 0 ° C to 150 ° C, preferably at temperatures from 0 ° C to 80 ° C.
  • the substances according to the invention have a strong microbicidal action and can be used to control unwanted microorganisms, such as fungi and bacteria, in crop protection and in material protection.
  • Fungicides can be used to control Plasmodiophoromycetes
  • Bactericides can be used in crop protection to combat Pseudomonadaceae, Rhizobiaceae, Enterobacteriaceae, Corynebacteriaceae and Streptomycetaceae.
  • pathogens of fungal and bacterial are exemplary but not limiting
  • Xanthomonas species such as, for example, Xanthomonas campestris pv. Oryzae;
  • Pseudomonas species such as, for example, Pseudomonas syringae pv. Lachrymans;
  • Erwinia species such as, for example, Erwinia amylovora;
  • Pythium species such as, for example, Pythium ultimum
  • Phytophthora species such as, for example, Phytophthora infestans
  • Pseudoperonospora species such as, for example, Pseudoperonospora humuli or
  • Plasmopara species such as, for example, Plasmopara viticola
  • Bremia species such as, for example, Bremia lactucae
  • Peronospora species such as, for example, Peronospora pisi or P. brassicae
  • Erysiphe species such as, for example, Erysiphe graminis
  • Sphaerotheca species such as, for example, Sphaerotheca fuliginea
  • Podosphaera species such as, for example, Podosphaera leucotricha
  • Venturia species such as, for example, Venturia inaequalis
  • Pyrenophora species such as, for example, Pyrenophora teres or P. graminea
  • Cochliobolus species such as, for example, Cochliobolus sativus
  • Drechslera (Conidial form: Drechslera, Syn: Helminthosporium);
  • Uromyces species such as, for example, Uromyces appendiculatus
  • Puccinia species such as, for example, Puccinia recondita
  • Sclerotinia species such as, for example, Sclerotinia sclerotiorum
  • Tilletia species such as, for example, Tilletia caries
  • Ustilago species such as, for example, Ustilago nuda or Ustilago avenae;
  • Pellicularia species such as, for example, Pellicularia sasakii;
  • Pyricularia species such as, for example, Pyricularia oryzae
  • Fusarium species such as, for example, Fusarium culmorum
  • Botrytis species such as, for example, Botrytis cinerea
  • Septoria species such as, for example, Septoria nodorum
  • Leptosphaeria species such as, for example, Leptosphaeria nodomm
  • Cercospora species such as, for example, Cercospora canescens
  • Alternaria species such as, for example, Alternaria brassicae
  • Pseudocercosporella species such as, for example, Pseudocercosporella he ⁇ otrichoides.
  • plants and parts of plants can be treated.
  • Plants are understood here to mean all plants and plant populations, such as desired and undesired wild plants or cultivated plants (including naturally occurring cultivated plants).
  • Cultivated plants can be plants by conventional breeding and optimization methods or by biotechnological and genetic engineering methods or combinations of these Methods can be obtained, including transgenic plants and including plant varieties that can or cannot be protected by plant breeders' rights.
  • Plant parts are to be understood to mean all above-ground and underground parts and organs of plants, such as sprout, leaf, flower and root, examples being leaves, needles, stems, stems, flowers, fruiting bodies,
  • Fruits and seeds as well as roots, tubers and rhizomes are listed.
  • the plant parts also include crops and vegetative and generative propagation material, for example cuttings, tubers, rhizomes, offshoots and seeds.
  • Active substances take place directly or by influencing their surroundings, living space or storage space according to the usual treatment methods, e.g. by dipping, spraying, vaporizing, atomizing, scattering, spreading and, in the case of propagation material, in particular seeds, furthermore by single- or multilayer coating.
  • the active compounds according to the invention can be used particularly successfully to combat rice diseases, for example against Pyricularia species.
  • the active compounds according to the invention are also suitable for increasing the crop yield. They are also less toxic and have good plant tolerance.
  • the active compounds can be converted into the customary formulations, such as solutions, emulsions, suspensions, powders, foams, pastes, granules, aerosols,
  • formulations are prepared in a known manner, for example by mixing the active ingredients with extenders, that is to say liquid solvents, pressurized liquefied gases and / or solid carriers, if appropriate using of surface-active agents, that is to say emulsifiers and / or dispersants and / or foam-generating agents.
  • extenders that is to say liquid solvents, pressurized liquefied gases and / or solid carriers, if appropriate using of surface-active agents, that is to say emulsifiers and / or dispersants and / or foam-generating agents.
  • organic solvents can, for example, also be used as auxiliary solvents.
  • aromatics such as xylene, toluene or alkylnaphthalenes, chlorinated aromatics or chlorinated aliphatic
  • Hydrocarbons such as chlorobenzenes, chlorethylenes or methylene chloride, aliphatic hydrocarbons such as cyclohexane or paraffins, e.g. Petroleum fractions, alcohols, such as butanol or glycol, and their ethers and esters, ketones, such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, highly polar solvents, such as dimethylformamide and dimethyl sulfoxide, and water.
  • Liquefied gaseous extenders or carriers mean liquids which are gaseous at normal temperature and pressure, e.g.
  • Aerosol propellants such as halogenated hydrocarbons as well as butane, propane, nitrogen and carbon dioxide.
  • Possible solid carriers are: e.g. natural rock meals, such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and synthetic rock meals, such as highly disperse silica, aluminum oxide and silicates.
  • the following 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.
  • Possible emulsifiers and / or foaming agents are: e.g. nonionic and anionic emulsifiers such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, e.g. Alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates and protein hydrolyzates.
  • Possible dispersants are: e.g. Lignin sulfite liquor and methyl cellulose.
  • Adhesives such as carboxymethyl cellulose, natural and synthetic polymers in the form of powders, granules or latices, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, and also 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, for example iron oxide, titanium oxide, fenocyanine blue and organic dyes such as alizarin, azo and metal phthalocyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc can be used .
  • the formulations generally contain between 0.1 and 95 percent by weight of active compound, preferably between 0.5 and 90%.
  • the active compounds according to the invention can also be used in a mixture with known fungicides, bactericides, acaricides, nematicides or insecticides, in order, for example, to broaden the spectrum of activity or to prevent the development of resistance.
  • fungicides bactericides
  • acaricides nematicides or insecticides
  • synergistic effects are obtained, i.e. the effectiveness of the mixture is greater than the effectiveness of the individual components.
  • Imazalil Imibenconazol, Iminoctadin, Iminoctadinealbesilat, Iminoctadinetriacetat, Iodocarb, Ipconazol, Iprobefos (IBP), Iprodione, Irumamycin, Isoprothiolan,
  • copper preparations such as: copper hydroxide, copper phthalate, copper oxychloride, copper sulfate, copper oxide, oxy-copper and Bordeaux mixture,
  • Mancopper Mancozeb, Maneb, Meferimzone, Mepanipyrim, Mepronil, Metalaxyl, Metconazol, Methasulfocarb, Methfuroxam, Metiram, Metomeclam, Metsulfovax, Mildiomycin, Myclobutanil, Myclozolin,
  • Paclobutrazole peognize, penconazole, pencycuron, phosdiphen, pimaricin, piperalin, polyoxin, polyoxorim, probenazole, prochloraz, procymidon, propamocarb,
  • Tebuconazole Tebuconazole, tecloftalam, tecnazen, tetcyclacis, tetraconazole, thiabendazole, thicyofen, thifluzamide, thiophanate-methyl, thiram, dioxymid, tolclofos-methyl, tolylfluanid, triadimefon, triadimenol, triazbutichl, triazoxid, triazoxid, triazoxid, triazoxide
  • N-formyl-N-hydroxy-DL-alanine sodium salt O, O-diethyl- [2- (dipropylamino) -2-oxoethyl] ethylphosphoramidothioate,
  • Chloethocarb Chlorethoxyfos, Chlorfenapyr, Chlorfenvinphos, Chlorfluazuron, Chlormephos, Chlo ⁇ yrifos, Chlo ⁇ yrifos M, Chlovaporthrin, Cis-Resmethrin, Cispermethrin, Clocythrin, Cloethocarb, Clofentezine, Cyanophoputhrin, Cycloprin, Cycloprin, Cycloprin M, Demeton S, Demeton-S-methyl, Diafenthiuron, Diazinon,
  • Halofenozide HCH, Heptenophos, Hexaflumuron, Hexythiazox, Hydroprene, Imidacloprid, isazofos, isofenphos, isoxathion, ivermectin,
  • Metolcarb Metoxadiazone, Mevinphos, Milbemectin, Monocrotophos,
  • Paecilomyces fumosoroseus Parathion A, Parathion M, Permethrin, Phenthoat, Phorat, Phosalone, Phosmet, Phosphamidon, Phoxim, Pirimicarb, Pirimiphos A,
  • Pirimiphos M Profenofos, Promecarb, Propoxur, Prothiofos, Prothoat, Pymetrozine,
  • Tefluthrin Temephos, Temivinphos, Terbufos, Tetrachlorvinphos, Thetacypermethrin, Thiamethoxam, Thiapronil, Thiatriphos, Thiocyclam hydrogen oxalate, Thiodicarb, Thiofanox, Thuringiensin, Tralocythrin, Tralomethrin
  • Triarathenes triazamates, triazophos, triazuron, trichlophenidines, trichlorfon,
  • the active compounds can be used as such, in the form of their formulations or the use forms prepared therefrom, such as ready-to-use solutions, suspensions, wettable powders, pastes, soluble powders, dusts and granules.
  • the Application takes place in the customary manner, for example by watering, spraying, atomizing, scattering, dusting, foaming, brushing, etc. It is also possible to apply the active ingredients by the ultra-low-volume process or to apply the active ingredient preparation or the active ingredient itself to the soil to inject.
  • the seeds of the plants can also be treated.
  • the application rates can be varied within a relatively wide range, depending on the type of application.
  • the active compound application rates are generally between 0.1 and 10,000 g / ha, preferably between 10 and 1,000 g / ha.
  • the active compound application rates are generally between 0.001 and 50 g per kilogram of seed, preferably between 0.01 and 10 g per kilogram of seed. In the treatment of the soil, the active compound application rates are generally between 0.1 and 10,000 g / ha, preferably between 1 and 5,000 g / ha.
  • the active substances are suitable for combating animal pests, in particular insects, arachnids and nematodes, which are found in agriculture, in forests, in the protection of Vonats 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 co ⁇ oris, Haematopinus spp., Linognathus spp., Trichodectes spp., Damalinia spp ..
  • Thysanoptera e.g. Hercinothrips femoralis, Thrips tabaci
  • Aleurodes brassicae Bemisia tabaci
  • Trialeurodes vaporariorum Aphis gossypii, Brevicoryne brassicae, Cryptomyzus ribis, Aphis fabae, Aphis pomi, Eriosoma lanigerum, Hyalopterus arundinis, Phylloxera vastatrix, Pemphigususpp.
  • Anthrenus spp. Attagenus spp., Lyctus spp., Meligethes aeneus, Ptinus spp., Niptus hololeucus, Gibbium psylloides, Tribolium spp., Tenebrio molitor, Agriotes spp., Conoderus spp., Melolontha melolontha, Costimallontra pursuits.
  • Hymenoptera e.g. Diprion spp., Hoplocampa spp., Lasius spp., Monomorium pharaonis, Vespa spp.
  • Plant-parasitic nematodes include e.g. Pratylenchus spp., Radopholus similis, Ditylenchus dipsaci, Tylenchulus semipenetrans, Heterodera spp., Globodera spp., Meloidogyne spp., Aphelenchoides spp., Longidorus spp., Xiphinema spp., Trichodorus spp., Bursaph.
  • the active ingredient When used against hygiene pests and pests of stored products, the active ingredient is distinguished by an excellent residual action on wood and clay as well as a good stability to alkali on limed substrates.
  • the 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, impregnated with active ingredients
  • 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, if appropriate using surface-active agents. thus 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
  • Possible solid carriers are: e.g. Ammonium salts and natural rock flours, 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 and 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 sulfite liquor and methyl cellulose.
  • Adhesives such as carboxymethyl cellulose, natural and synthetic polymers in the form of powders, granules or latices, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, and natural phospho- lipids such as cephalins and lecithins and synthetic phosphophides.
  • Other additives can be mineral and vegetable oils.
  • Dyes such as inorganic pigments, e.g. Iron oxide, titanium oxide, fenocyanine 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 substance according to the invention can be present in its commercially available formulations and in the use forms prepared from these formulations in a mixture with other active substances, such as insecticides, attractants, sterilants, bactericides, acaricides, nematicides, fungicides, growth-regulating substances or herbicides.
  • Insecticides include, for example, phosphoric acid esters, carbamates, carboxylic acid esters, chlorinated hydrocarbons, phenylureas, substances produced by microorganisms, etc.
  • 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 through which the action of the active ingredients is increased 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 substance When used against hygiene and Vonat pests, the active substance is characterized by an excellent residual effect on wood and clay as well as a good stability to alkali on limed substrates.
  • the compounds V-2 to V-5 were further implemented without purification.
  • Chlorine is passed into a solution of 12.3 g of 5,5-dichloro-3- (4-chloro-phenyl) -4-pentenoate in 100 ml of carbon tetrachloride until complete conversion is reached after about an hour (monitored by regular GC analyzes ). Dissolved chlorine is blown out with argon and then the solvent is removed under reduced pressure. 15.2 g (99% of theory) of 4,5,5,5-tetrachloro-3- (4-chloro-phenyl) -pentanoic acid methyl ester are obtained as a mixture of two diastereoisomers.
  • Solvent 48.8 parts by weight of N, N-dimethylformamide emulsifier: 1.2 parts by weight of alkylaryl polyglycol ether
  • Solvent 7 parts by weight of dimethylformamide emulsifier: 1 part by weight of alkylaryl polyglycol ether
  • active compound 1 part by weight of active compound is mixed with the stated amount of solvent and the stated amount of emulsifier, and the concentrate is diluted with water to the desired concentration.
  • Cabbage leaves (Brassica oleracea) are treated by being dipped into the preparation of active compound of the desired concentration and populated with caterpillars of the cabbage cockroach (Plutella maculipennis) while the leaves are still moist.
  • the kill is determined in%. 100% means that all caterpillars have been killed; 0% means that no caterpillars have been killed.

Landscapes

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

Abstract

L'invention concerne de nouveaux composés halogène, leur procédé de production et leur utilisation pour traiter les plantes contre l'attaque de micro-organismes et insectes phytopathogènes. L'invention concerne également de nouveaux produits intermédiaires et leurs procédés de production.
EP00931134A 1999-05-19 2000-05-08 Composes halogene Withdrawn EP1181267A1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE19922934A DE19922934A1 (de) 1999-05-19 1999-05-19 Neue Halogenverbindungen
DE19922934 1999-05-19
PCT/EP2000/004102 WO2000071500A1 (fr) 1999-05-19 2000-05-08 Composes halogene

Publications (1)

Publication Number Publication Date
EP1181267A1 true EP1181267A1 (fr) 2002-02-27

Family

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Application Number Title Priority Date Filing Date
EP00931134A Withdrawn EP1181267A1 (fr) 1999-05-19 2000-05-08 Composes halogene

Country Status (5)

Country Link
EP (1) EP1181267A1 (fr)
JP (1) JP2003500377A (fr)
AU (1) AU4917700A (fr)
DE (1) DE19922934A1 (fr)
WO (1) WO2000071500A1 (fr)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR100718863B1 (ko) * 1999-08-18 2007-05-16 바이엘 크롭사이언스 게엠베하 살진균제
US20060122065A1 (en) * 2002-12-24 2006-06-08 Hiroshi Sakaguchi Amide compound and method of controlling plant disease with the same
US7902400B2 (en) 2005-10-27 2011-03-08 Sumitomo Chemical Company, Limited Amide compounds and their use

Family Cites Families (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5246019A (en) * 1975-10-06 1977-04-12 Sumitomo Chem Co Ltd Process for preparation of alkyl-3-(2,2-dihalovinyl)-4-methyl-4-penten oate and its derivatives
GB1503857A (en) * 1976-05-25 1978-03-15 Cheminova As Production of chrysanthemic acid esters and homologues thereof
DE2710174A1 (de) * 1977-03-09 1978-09-14 Bayer Ag Verfahren zur herstellung von dihalogenvinyl-cyclopropancarbonsaeuren und deren ester
DE2810031A1 (de) * 1977-03-11 1978-09-21 Kuraray Co Alpha- oder beta- substituierte isovaleriansaeureester enthaltendes schaedlingsbekaempfungsmittel
YU128891A (sh) * 1990-07-27 1994-06-10 Ciba Geigy Ag. Derivati karboksimetilciklopropana
GB9113624D0 (en) * 1991-06-25 1991-08-14 Wellcome Found Pesticides
DE4123585C1 (en) * 1991-07-12 1992-11-05 Schering Ag Berlin Und Bergkamen, 1000 Berlin, De Fluoroolefin for insecticide and nematocide - prepd. by reacting fluoroolefin intermediate with phosphonium salt in base, for high acaricidal activity
CA2230031A1 (fr) * 1995-08-25 1997-03-06 Bayer Aktiengesellschaft Derives de 4,4-difluoro-3-butenylester ou de 4,4-difluoro-3-halogeno-3-butenylester et leur utilisation en tant que parasiticides
DE19542935A1 (de) * 1995-11-17 1997-05-22 Bayer Ag Fluorbutenoyloxyessigsäureamide

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO0071500A1 *

Also Published As

Publication number Publication date
WO2000071500A1 (fr) 2000-11-30
DE19922934A1 (de) 2000-11-23
JP2003500377A (ja) 2003-01-07
AU4917700A (en) 2000-12-12
WO2000071500A8 (fr) 2001-02-22

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