EP1444221A1 - Nitrobutadienes halogenes servant a lutter contre les parasites animaux - Google Patents

Nitrobutadienes halogenes servant a lutter contre les parasites animaux

Info

Publication number
EP1444221A1
EP1444221A1 EP02777324A EP02777324A EP1444221A1 EP 1444221 A1 EP1444221 A1 EP 1444221A1 EP 02777324 A EP02777324 A EP 02777324A EP 02777324 A EP02777324 A EP 02777324A EP 1444221 A1 EP1444221 A1 EP 1444221A1
Authority
EP
European Patent Office
Prior art keywords
spp
methyl
optionally substituted
compounds
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Withdrawn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
EP02777324A
Other languages
German (de)
English (en)
Inventor
Reiner Fischer
Peter Jeschke
Angelika Lubos-Erleden
Peter Lösel
Udo Reckmann
Dieter Kaufmann
Viktor Zapolskil
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 CropScience 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 CropScience AG filed Critical Bayer CropScience AG
Publication of EP1444221A1 publication Critical patent/EP1444221A1/fr
Withdrawn legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/50—1,3-Diazoles; Hydrogenated 1,3-diazoles
    • 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
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/84—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms six-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,4
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
    • C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
    • C07D491/10—Spiro-condensed systems

Definitions

  • the present application relates to new unsaturated compounds, processes for their preparation and their use for controlling animal pests.
  • halogen-substituted 1,3-butadienes such as 4-bromo-2-nitro-l, l, 3,4-tetrachloro-l, 3-butadiene (Yu. A. Ol'dekop et al., Zh. Org Khim. 15, 6, 1979, pp. 1321-1322; Vl Potkin et al., Zh.Org. Khim. 31, 2, 1995, pp. 1816-1822), 2-nitro-l, l, 3, 4,4-pentachor-1,3-butadiene (Yu. A. Ol'dekop et al., Zh. Org. Khim. 12, 9, 1976, pp. 2039-2040; Potkin et al., Dokl. Nats. Akad. Nauk Belarusi 40, 1, 1996, p.
  • trichlonitrodienamino-adamantane derivatives such as, for example, 1, 1-bis [1 - (1-adamantyl) ethylamino] -3,4,4-trichloro-2-nitro-1,3-butadiene, are antitumor-active compounds in vitro (cf. EV Vashkevich et al., Russ. J. Org. Chem. 35, 12, 1999, pp. 1773-1776).
  • A represents in each case optionally substituted cycloalkyl, heterocyclyl, aryl or hetaryl,
  • R 1 represents hydrogen or alkyl
  • R 2 represents hydrogen or alkyl
  • Z represents halogen or NO2
  • X represents OR 3 , SR 3 or NR 4 R 5 ,
  • Y represents hydrogen, halogen, OR 6 , SR 6 or NR 7 R 8 ,
  • R 3 for each optionally substituted and optionally interrupted by one or more heteroatoms alkyl, alkenyl, cycloalkyl,
  • R 4 and R 5 independently of one another for hydrogen, for alkyl, alkenyl, alyl, cycloalkyl, cyclo- alkylalkyl, alkoxycarbonyl or represents in each case optionally substituted aryl, hetaryl, arylalkyl or hetarylalkyl,
  • R 4 and R 5 together with the nitrogen atom to which they are attached form a ring which is optionally interrupted by one or more further heteroatoms and is optionally substituted,
  • R 6 represents alkyl, alkenyl, cycloalkyl, cycloalkylalkyl or optionally substituted aryl or arylalkyl which is optionally interrupted by one or more heteroatoms and is optionally substituted,
  • R 7 and R 8 independently of one another represent optionally interrupted by one or more heteroatoms and in each case optionally substituted alkyl, alkenyl, cycloalkyl, cycloalkylalkyl or optionally substituted aryl, hetaryl, arylalkyl or hetarylalkyl, or
  • R 7 and R 8 together with the nitrogen atom to which they are attached form a ring which is optionally interrupted by one or more further heteroatoms and is optionally substituted
  • R 3 together with the atoms linking them form an optionally interrupted by one or more further heteroatoms and optionally substituted ring or R 2 and R 5 together with the atoms linking them form a ring which is optionally interrupted by one or more further heteroatoms and is optionally substituted.
  • Y 1 represents hydrogen or chlorine
  • D represents in each case optionally substituted -CH2-CH2- or -CH2-CH2-CH2-, RI
  • B represents OH, SH or NH
  • a and R 1 have the meanings given above and
  • R 1 , D, Y 1 and Z have the meanings given above and
  • IB 1 stands for O, S or N.
  • A, R 1 , D, B 1 and Z have the meanings given above and Y 2 represents OR 6 , SR 6 or NR 7 R 8 ,
  • R 6 , R 7 and R 8 have the meanings given above
  • Y 1 represents chlorine
  • Alkyl alone or as part of a radical in the general formulas means straight-chain or branched alkyl having preferably 1 to 6, in particular 1 to 4, carbon atoms. Examples include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl,
  • Methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl and tert-butyl may preferably be mentioned.
  • Alkenyl alone or as part of a radical in the general formulas means straight-chain or branched alkenyl with preferably 2 to 6, in particular 2 to
  • Examples include vinyl, 2-propenyl, 2-butenyl, 3-butenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-2- butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, l-methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl, l, l-dimethyl 2-propenyl, l, 2-dimethyl-2-propenyl, 1-ethyl-2-propenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl, 1-
  • 2-propenyl, 2-butenyl or 1-methyl-2-propenyl may be mentioned.
  • Alkynyl alone or as part of a radical in the general formulas means straight-chain or branched alkynyl having preferably 2 to 6, in particular 3 to 4, carbon atoms. Examples include optionally substituted 2-propynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, 1-
  • Cycloalkyl alone or as part of a radical in the general formulas means mono-, bi- and tricyclic cycloalkyl, preferably having 3 to 10, in particular 3, 5 or 7, carbon atoms. Examples include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, bicyclo [2.2.1] heptyl, bicyclo [2.2.2] octyl and adamantyl.
  • Haloalkyl alone or as part of a radical in the general formulas contains 1 to 4, in particular 1 or 2, carbon atoms with preferably 1 to 9, in particular 1 to 5 identical or different halogen atoms, preferably fluorine, chlorine or bromine, in particular fluorine or chlorine.
  • halogen atoms preferably fluorine, chlorine or bromine, in particular fluorine or chlorine.
  • Examples include trifluoromethyl, trichloromethyl, chlorodifluoromethyl, dichlorofluoromethyl, chloromethyl, bromomethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2,2,2-trichloroethyl,
  • Alkoxy alone or as part of a radical in the general formulas means straight-chain or branched alkoxy with preferably 1 to 6, in particular 1 to 4, carbon atoms. Examples include methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, sec-butoxy and tert-butoxy.
  • Alkoxyalkoxy alone or as part of a radical in the general formulas means straight-chain or branched alkoxyalkoxy with preferably 2 to 6, in particular 2 to 4, carbon atoms. Substituted methoxymethoxy, methoxyethoxy, methoxy-n-propoxy and ethoxyisopropoxy may be mentioned as examples.
  • Alkoxyalkoxyalkoxy alone or as part of a radical in the general formulas means straight-chain or branched alkoxyalkoxyalkoxy, preferably example 3 to 6, in particular 3 to 4 carbon atoms.
  • Examples include methoxy-methoxyethoxy, methoxy-ethoxyethoxy and methoxyethoxy-n-propoxy.
  • Haloalkoxy alone or as part of a radical in the general formulas means straight-chain or branched haloalkoxy with preferably 1 to 6, in particular 1 to 4, carbon atoms.
  • Examples include optionally substituted difluoromethoxy, trifluoromethoxy, trichloromethoxy, chlorodifluoromethoxy, 1-fluoroethoxy, 2-fluoroethoxy, 2,2-difluoroethoxy, 1,1,2,2-tetrafluoroethoxy, 2,2,2-trifluoroethoxy and 2-chloro called l, l, 2-trifluoroethoxy.
  • Alkylthio alone or as part of a radical in the general formulas means straight-chain or branched alkylthio with preferably 1 to 6, in particular 1 to 4, carbon atoms. Examples include methylthio, ethylthio, n-propylthio, isopropylthio, n-butylthio, isobutylthio, sec-butylthio and tert-butylthio.
  • Haloalkylthio alone or as part of a radical in the general formulas means straight-chain or branched haloalkylthio with preferably 1 to 6, in particular 1 to 4, carbon atoms. Examples include difluoromethylthio, trifluoromethylthio, trichloromethylthio, chlorodifluoromethylthio, 1-fluoroethylthio, 2-
  • Alkylcarbonyl alone or as part of a radical in the general formulas means straight-chain or branched alkylcarbonyl with preferably 1 to 6, in particular 1 to 4, carbon atoms in the alkyl part.
  • Examples of optionally substituted methylcarbonyl, ethylcarbonyl, n-propylcarbonyl, isopropylcarbonyl, sec-butylcarbonyl and tert-butylcarbonyl may be mentioned.
  • Formula means mono-, bi- and tricyclic cyclo-alkylcarbonyl, preferably with 3 to 10, in particular 3, 5 or 7 carbon atoms in the cycloalkyl part.
  • Examples include cyclopropylcarbonyl, cyc-lobutylcarbonyl, cyclopentylcarbonyl, cyclohexylcarbonyl, cycloheptylcarbonyl, cyclooctylcarbonyl, bicyclo [2.2.1] heptylcarbonyl, bicyclo [2.2.2] octylcarbonyl and adamantylcarbonyl.
  • Alkoxycarbonyl alone or as part of a radical in the general formulas means straight-chain or branched alkoxycarbonyl with preferably 1 to 6, in particular 1 to 4, carbon atoms in the alkoxy part. Examples include methoxycarbonyl, ethoxycarbonyl, n-propoxycarbonyl, isopropoxycarbonyl, n-butoxycarbonyl, isobutoxycarbonyl, sec-butoxycarbonyl and tert-butoxycarbonyl.
  • Aryl is, for example, a mono-, di-, or multinuclear aromatic radical such as phenyl, naphthyl, tetrahydronaphthyl, indanyl, fluorenyl, but preferably phenyl or naphthyl, especially phenyl.
  • Arylalkyl in the general formulas preferably means arylalkyl optionally substituted in the aryl part and / or alkyl part, preferably having 6 or 10, in particular 6, carbon atoms in the aryl part (preferably phenyl or naphthyl, in particular phenyl) and preferably 1 to 4, in particular 1 or 2, carbon atoms in the Alkyl part, where the alkyl part can be straight-chain or branched. Examples include benzyl and 1-phenylethyl.
  • the optionally substituted radicals of the general formulas can carry one or more, preferably 1 to 3, in particular 1 to 2 identical or different substituents.
  • Examples of preferred substituents are:
  • Alkylthio such as methylthio, ethylthio, n-propylthio, isopropylthio, n- Butylthio, isobutylthio, sec-butylthio;
  • Haloalkyl preferably having 1 to 5, in particular 1 to 3, halogen atoms, the halogen atoms being identical or different and being halogen atoms, preferably fluorine, chlorine or bromine, in particular fluorine or chlorine, such as difluoromethyl, trifluoromethyl, trichloromethyl; hydroxy; Halogen, preferably fluorine, chlorine, bromine and iodine, especially fluorine and chlorine; cyano; nitro; amino; Monoalkyl- and dialkylamino with preferably 1 to 4, in particular 1 or 2 carbon atoms per alkyl group, such as methylamino, methylethylamino, dimethylamino, n-propylamino, isopropy
  • alkyl means straight-chain or branched alkyl having preferably 1 to 6, in particular 1 to 4, carbon atoms.
  • substituted mono- or dialkylamino groups are methylamino, ethylamino, dimethylamino, diethylamino, di-n-propylamino, diisopropylamino or dibutylamino.
  • alkoxyalkyl means straight-chain or branched Alkoxyalkyl with preferably 2 to 6, in particular 2 to 4 carbon atoms.
  • substituted mono- or dialkoxyalkylamino groups are methoxymethylamino, methoxyethylamino, di- (methoxymethyl) -amino or di- (methoxyethyl) -amino.
  • Suitable cyclic amino groups are heteroaromatic or aliphatic ring systems with one or more nitrogen atoms as the heteroatom, in which the heterocycles can be saturated or unsaturated, one ring system or more condensed ring systems, and optionally further heteroatoms such as one or two nitrogen, oxygen and contain sulfur, etc.
  • cyclic amino groups can also mean a spiro ring or bridged ring system.
  • the number of atoms which form cyclic amino groups is not limited, for example they consist of 3 to 8 atoms in the case of a single-ring system and 7 to 11 atoms in the case of a three-ring system.
  • cyclic amino groups with saturated and unsaturated monocyclic groups with a nitrogen atom as heteroatom are 1-azetidinyl, pyrrolidino, 2-pyrrolin-l-yl, 1-pyrrolyl, piperidino, 1,4-dihydropyrazin-l-yl, 1, 2,5,6-tetrahydropyrazin-1-yl, 1,4-dihydropyridin-l-yl, 1,2,5,6-tetrahydropyridin-l-yl,
  • cyclic amino groups with saturated and unsaturated monocyclic groups with two or more nitrogen atoms as heteroatoms are 1-imidazolidinyl, 1-imidazolyl, 1-pyrazolyl, 1-triazolyl, 1-tetrazolyl, 1-piperazinyl, 1-homopiperazinyl, 1,2- Called dihydro-pyridazin-1-yl, 1,2-dihydro-pyrimidin-l-yl, perhydropyrimidin-1-yl, 1,4-diazacycloheptan-l-yl; exemplary of cyclic amino groups with saturated and unsaturated monocyclic groups with one or two oxygen atoms and one to 3 nitrogen atoms as heteroatoms, such as, for example, oxazolidin-3-yl, 2,3-dihydroisoxazol-2-yl, isoxazol-2-yl, 1,2 , 3-oxadiazin-2-yl, morpholino,
  • Groups with one to three nitrogen atoms and one or two sulfur atoms heteroatoms which may be mentioned are thiazolidin-3-yl, isothiazolin-2-yl, thiomorpholino or dioxothiomo ⁇ holino;
  • examples of cyclic amino groups with saturated and unsaturated condensed cyclic groups are indol-1-yl, 1,2-dihydrobenzimidazol-l-yl, perhydropyrrolo [1,2-a] pyrazin-2-yl;
  • an example for cyclic amino groups with spirocyclic groups is the 2-
  • Called Azaspiro [4,5] decan-2-yl; 2-Azabicyclo [2,2, l] heptan-7-yl may be mentioned as an example of cyclic amino groups with bridged heterocyclic groups.
  • the compounds according to the invention are generally defined by the formula (I).
  • A preferably represents optionally by halogen, (fluorine, chlorine, bromine),
  • A preferably furthermore stands for pyrazolyl, 1,2,4-triazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, 1,2,5-thiadiazolyl, pyridyl, pyrazinyl or
  • Pyrimidinyl which is optionally substituted by fluorine, chlorine, bromine, cyano, nitro, C 1 -C 4 -alkyl (which is optionally substituted by fluorine and / or chlorine), C 1 -C 4 alkoxy (which is optionally substituted by fluorine and / or chlorine) , -C-C 2 - Alkylthio (which is optionally substituted by fluorine and / or chlorine) or C] -C 2 alkylsulfonyl (which is optionally substituted by fluorine and / or chlorine) are substituted.
  • A furthermore represents a saturated C 5 -C 6 cycloalkyl radical which is optionally substituted by halogen or -CC alkyl, in which a methylene group is optionally replaced by O or S.
  • R 1 preferably represents hydrogen, methyl, ethyl, n-propyl or i-propyl.
  • R 2 preferably represents hydrogen, methyl, ethyl, n-propyl or i-propyl.
  • Shark is preferably bromine or chlorine.
  • X preferably represents OR 3 , SR 3 or NR 4 R 5 .
  • Y preferably represents hydrogen, halogen (especially chlorine), OR, SR or NR'R *
  • Z preferably represents bromine, chlorine or nitro.
  • R 3 preferably represents in each case optionally interrupted by oxygen or sulfur and optionally substituted by halogen, hydroxy or cyano straight-chain or branched C ⁇ -6 - alkyl, C 3rd 6 - alkenyl, C -7 - cycloalkyl, C 3-7 -cycloalkyl-C ⁇ -2 -alkyl, for optionally by C j ⁇ alkyl, C ⁇ haloalkyl, halogen, C 4- alkoxy, C ⁇ haloalkoxy, nitro or cyano substituted phenyl -CC -2 alkyl, phenyl, pyridyl, thiazolyl, pyrazolyl or pyrimidyl or
  • R 2 and R 3 preferably represent a C2 .4 -alkylidendiyl group which is optionally substituted by C 4 -C 4 -alkyl
  • R 4 and R 5 are preferably, and independently represent hydrogen, in each case optionally interrupted by oxygen or sulfur, and in each case optionally halogen-substituted straight-chain or branched C ⁇ -6 alkyl, C 3-6 alkenyl, C 3-6 alkynyl, C 3-7 cycloalkyl, C 3-7 cycloalkyl-C ⁇ -6 - substituted alkyl, C ⁇ -6 alkoxycarbonyl or unsubstituted or C ⁇ 4 alkyl, C j _2- haloalkyl or halogen, phenyl-C ⁇ -2 alkyl, pyridyl .
  • R and R are further preferred and together with the N atom to which they are attached for a 4-, 5-, 6- or 7-membered ring or for a 7- to
  • 10-membered bicyclic optionally interrupted by oxygen, sulfur, sulfoxyl, sulfonyl, carbonyl, NR 6 or by quaternized nitrogen and is optionally substituted by C j .4 alkyl substituted, or
  • R 2 and R 5 together with the atoms linking them, preferably represent an optionally by C j . 4 - alkyl substituted saturated 5-, 6- or 7- membered ring, which apart from the two nitrogen atoms no further
  • R 6 preferably represents in each case optionally interrupted by oxygen or sulfur and optionally substituted by fluorine or chlorine, straight-chain or branched C ⁇ -6 - alkyl, C 3-6 alkenyl, C 5-7 cycloalkyl, C 3- 7- cycloalkyl-C -2 alkyl or for each optionally by halogen, C j _ 4 - alkyl, C j .
  • R 7 and R 8 are preferably independently of one another represent in each case optionally interrupted by oxygen or sulfur and optionally substituted by fluorine, chlorine-substituted straight-chain or branched C ⁇ -6 alkyl, C 3-6 - alkenyl, C 3 _ cycloalkyl, C 3- -Cycloalkyl-C ⁇ -6-alkyl, each optionally by C 1 . 4 - alkyl, C ⁇ -alkoxy, halogen, C ⁇ -haloalkyl,
  • R and R are further preferred and together with the N atom to which they are attached represent a 4-, 5-, 6- or 7-membered ring or a 7- to
  • 11-membered bicycles which may also be replaced by oxygen, Sulfur, sulfoxyl, sulfonyl, carbonyl, -NR 6 or interrupted by quartemis believing nitrogen and optionally substituted by C 1. 4 - substituted alkyl.
  • a furthermore particularly preferably represents an optionally substituted by halogen (in particular chlorine) or C 1 -C 3 -alkyl (in particular methyl)
  • R 1 particularly preferably represents hydrogen or methyl.
  • R particularly preferably represents hydrogen, methyl or ethyl.
  • Shark is particularly preferably bromine or chlorine.
  • X particularly preferably represents SR 3 or NR 4 R 5 .
  • Y particularly preferably represents hydrogen, chlorine, SR or NR R.
  • Z particularly preferably represents chlorine or nitro.
  • R, 3 particularly preferably represents straight-chain or branched C-alkyl, in particular methyl, ethyl, propyl, isopropyl, isobutyl, sec-butyl, tert-butyl, hydroxyl-C-alkyl, in particular 2-hydroxyethyl, 3-hydroxypropyl, C 3-4 - alkenyl, especially 2-propenyl, 2-butenyl, C 5-7 -cycloalkyl, especially cyclopentyl, cyclohexyl, C -7- cycloalkyl-C] -2- alkyl, especially cyclopropylmethyl, optionally by fluorine, chlorine , Bromine, C j . 4 alkyl, C j . 4 - alkoxy, C ⁇ haloalkyl, C ⁇ haloalkoxy, nitro or cyano substituted phenyl or benzyl or
  • R 2 and R 3 are particularly preferably a C2_3-alkylidenediyl group.
  • R 4 and R 5 are particularly preferably and independently of one another hydrogen, straight-chain or branched C 1- alkyl or C j .
  • R 4 and R 5 furthermore particularly preferably represent optionally substituted by methyl or ethyl, optionally substituted by oxygen, sulfur or N-
  • R 6 interrupted C 4 _6-alkylidene diyl, especially together with the N-
  • R 2 and R 5 together with the atoms linking them particularly preferably represent a saturated 5-, 6- or 7-membered ring which contains no further heteroatoms in addition to the two nitrogen atoms.
  • R 6 particularly preferably represents straight-chain or branched C 4 alkyl, in particular methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, allyl, or each optionally by fluorine, chlorine, bromine , C j . 4 - alkyl, C 1 .2- alkoxy, trifluoromethyl, trifluoromethoxy, cyano or nitro substituted phenyl or benzyl
  • R and R are particularly preferably and independently of one another straight-chain or branched C-alkyl, in particular methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, C 3-4 alkenyl, in particular 2-propenyl, 2-butenyl, C 3-7 cycloalkyl, especially cyclopropyl, cyclobutyl,
  • R and R are furthermore particularly preferred and, together with the N atom to which they are attached, represent a 5-, 6- or 7-ring or a 7- to 11-membered bicyclic radical, which may also be replaced by oxygen, sulfur,
  • Carbonyl, N-methyl, N-ethyl, N-allyl, N-phenyl, N-chlorophenyl, N-benzyl are interrupted and are optionally substituted by methyl or ethyl.
  • R 1 very particularly preferably represents hydrogen or methyl.
  • R 2 very particularly preferably represents hydrogen or methyl.
  • Shark very particularly preferably represents bromine and chlorine, especially chlorine.
  • X very particularly preferably represents SR 3 or NR 4 R.
  • Y very particularly preferably represents chlorine, SR 6 or NR 7 R 8 .
  • Z very particularly preferably represents chlorine.
  • R very particularly preferably represents methyl or phenyl.
  • R and R very particularly preferably represent a C2_3-alkylidenediyl group.
  • R 4 and R 5 are very particularly preferably and independently of one another
  • R and R very particularly preferably, together with the atoms linking them, represent a saturated 5- or 6-membered ring which is adjacent to the two
  • Nitrogen atoms contains no further heteroatoms.
  • R 6 very particularly preferably represents straight-chain or branched C M alkyl, in particular methyl, ethyl, propyl, isopropyl, isobutyl, sec-butyl, tert-butyl, allyl or, in each case, optionally by fluorine, chlorine, bromine, methyl,
  • R 7 and R 8 very particularly preferably and independently of one another represent straight-chain or branched C M alkyl, in particular methyl, ethyl, propyl,
  • R and R are also very particularly preferred and together with the N atom to which they are attached for a 5-, 6- or 7-membered ring or for a 7- to 11-membered bicyclus, which may also be by Oxygen, sulfur, carbonyl, N-methyl, N-ethyl, N-allyl, N-phenyl, N-chloro-phenyl, N-benzyl are interrupted and are optionally substituted by methyl.
  • R 1 represents hydrogen
  • Z represents chlorine
  • shark represents chlorine
  • R 2 and X for a radical -CH 2 -CH 2 -CH 2 -N ⁇ -.
  • Y represents NR 7 R 8 and
  • R 7 and R 8 together with the nitrogen atom to which they are attached represent a 5-, 6- or 7-membered ring which may be interrupted by oxygen, sulfur or NR 6 .
  • the compounds of the general formula (I) are new and can be prepared, for example, by the processes specified above.
  • the compounds of the general formula (I) can optionally be formed as a mixture of E and Z isomers in the process according to the invention.
  • Formula (H) provides a general definition of the halogen-substituted 1,3-butadienes required as starting materials for carrying out the process according to the invention.
  • halogen-substituted 1,3-butadienes used as starting materials are known from (see Yu. A. Ol'dekop et al, Zh. Org. Khim. 15, 6, 1979, pp. 1321-1322; VI Potkin et al, Zh Org. Khim. 31, 2, 1995, pp. 1816-1822; Yu. A. Ol'dekop et al, Zh. Org. Khim. 12, 9, 1976, pp. 2039-2040; Potkin et al, Dokl Nats. Akad. Nauk Belarusi 40, 1, 1996, pp. 68-71; NI Nechai et al., Dokl. Nats. Akad. Nauk Belarusi 42, 2, 1998, pp. 75-78).
  • NHR 4 DE-OS 19710613, JP-Pat. 07242633, JP Pat. 06016636, JP Pat. 05310697, JP Pat. 04217957, EP 609811, EP 542086, EP 474057, EP 163855; S. Kagabu et al., Biosci., Biotechnol., Biochem. 62, 6, 1998, pp. 1216-1224) can be obtained.
  • Diluents are advantageously used in an amount such that the reaction mixture remains readily stirrable throughout the process. Diluents for carrying out the process according to the invention are all compared to
  • Reactants inert organic solvents in question include: halogenated hydrocarbons, in particular chlorinated hydrocarbons, such as tetrachlorethylene, tetrachloroethane, dichloropropane, methylene chloride, dichlorobutane, chloroform, carbon tetrachloride, trichloroethane, trichloroethylene, pentachloroethane, difluorobenzene, 1, 2-chlorobenzene, 1, 2-chlorobenzene, 1, 2-chlorobenzene, 1, 2-dichlorobenzene, 1, 2-dichloro-benzene Dichlorobenzene, chlorotoluene, trichlorobenzene; Alcohols such as methanol, ethanol, isopropanol, tert-butanol; Ethers such as ethyl propyl ether, methyl tert-butyl ether, n-butyl ether, ani
  • preferred diluents for carrying out the process according to the invention are nitriles such as acetonitrile, propionitrile, butyronitrile or isobutyronitrile, in particular acetonitrile or propionitrile, esters such as methyl, ethyl, butyl, isobutyl acetate, in particular methyl acetate and ethyl acetate; Amides such as N, N-dimethylformamide, N, N, -dimethylacetamide, N, N-dipropylformamide, N, N-dibutyl-formamide, N-methylpyrrolidone, in particular N, N-dimethylformamide, N, N, -dimethylacetamide and N -Methylpyrrolidone, alcohols such as methanol, ethanol, isopropanol, tert-butanol, especially methanol, ethers such as ethyl propyl ether
  • reaction of compounds of the general formula (II) by the process according to the invention is carried out by reacting the halogen-substituted 1,3-butadienes of the general formula (H) in the presence of a compound of the general formula (in) in one of the specified diluents ,
  • the reaction time is 10 minutes to 48 hours.
  • the reaction takes place at temperatures between -100 ° C and + 70 ° C, preferably between -78 ° C and + 50 ° C, particularly preferably between -50 ° C and + 30 ° C.
  • the process is preferably carried out at normal pressure and, if appropriate, under a protective gas atmosphere (nitrogen or argon). But you can also work under increased pressure.
  • reaction products are separated off in the customary manner. They can be purified by recrystallization, vacuum distillation or column chromatography (see also the preparation examples).
  • the compounds of the general formula (Ib) can optionally be formed as a mixture of E and Z isomers in the process according to the invention.
  • Formula (Ia) provides a general definition of the halogen-substituted 1,3-butadienes required as starting materials for carrying out the process according to the invention.
  • Y 1 represents halogen, in particular chlorine.
  • halogen-substituted 1,3-butadienes used as starting materials can be obtained by the process mentioned above.
  • Diluents are advantageously used in an amount such that the reaction mixture remains readily stirrable throughout the process.
  • Suitable diluents for carrying out the process according to the invention are all inert organic solvents mentioned above.
  • preferred diluents for carrying out the process according to the invention are nitriles such as acetonitrile, propionitrile, butyronitrile, isobutyronitrile, in particular acetonitrile or propionitrile, amides such as N, N-dimethylformamide, N, N, -dimethylacetamide, N, N-dipropylformamide, N, N-dibutyl -formamide, N-
  • nitriles such as acetonitrile, propionitrile, butyronitrile, isobutyronitrile, in particular acetonitrile or propionitrile
  • amides such as N, N-dimethylformamide, N, N, -dimethylacetamide, N, N-dipropylformamide, N, N-dibutyl -formamide, N-
  • Methyl pyrrolidone especially N, N-dimethylformamide, N, N, -dimethylacetamide and N-methylpyrrolidone, alcohols such as methanol, ethanol, isopropanol, tert-butanol, in particular methanol and dimethyl sulfoxide.
  • reaction of compounds of general formula (Ia) by the process according to the invention is carried out by reacting the compounds of general formula (Ia) in the presence of a compound of general formula (IV) in one of the specified diluents.
  • the reaction time is 10 minutes to 48 hours.
  • the reaction takes place at temperatures between -70 ° C and + 200 ° C, preferably between -30 ° C and + 150 ° C, particularly preferably between 0 ° C and + 100 ° C.
  • the process is preferably carried out at normal pressure and, if appropriate, under a protective gas atmosphere (nitrogen or argon). But you can also work under increased pressure.
  • reaction products are separated off in the customary manner. They can be purified in the usual way by recrystallization, vacuum distillation or column chromatography (see also the preparation examples).
  • the active substances are suitable for combating animal pests, in particular insects, arachnids and nematodes, which occur in agriculture, in forests, in the protection of stored goods and materials, and in the hygiene sector. They can preferably be used as pesticides. They are effective against normally sensitive and resistant species as well as against all or individual stages of development.
  • the pests mentioned above include: From the order of the Isopoda, for example 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 for example Hercinothrips femoralis, Thrips tabaci, Thrips palmi, Frankliniella accidentalis.
  • Heteroptera for example Eurygaster spp., Dysdercus intermedius, Piesma quadrata, Cimex lectularius, Rhodnius prolixus, Triatoma spp.
  • Homoptera e.g. Aleurodes brassicae, Bemisia tabaci, Trialeurodes vaporariorum, Aphis gossypii, Brevicoryne brassicae, Cryptomyzus ribis, Aphis fabae, Aphis pomi, Eriosoma lanigerum, Hyalopterus arundinis, Phylloxera vastatrix, Pemphigus sppe, Phros
  • Empoasca spp. Euscelis bilobatus, Nephotettix cincticeps, Lecanium corni, Saissetia oleae, Laodelphax striatellus, Nilaparvata lugens, Aonidiella aurantii, Aspidiotus hederae, Pseudococcus spp., Psylla spp.
  • Sitophilus spp. Sitophilus spp., Otiorrhynchus sulcatus, Cosmopolites sordidus, Ceuthorrhynchus assimilis, Hypera postica, Dermestes spp., Trogoderma spp., Anthrenus spp., Attagenus spp., Lyctus spp., Meligethes aeneus, Ptinusium sppyl., Ptinus holpp.
  • Tribolium spp. 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.
  • Oestrus spp. Hypoderma spp., Tabanus spp., Tannia spp., Bibio hortulanus, Oscinella frit, Phorbia spp., Pegomyia hyoscyami, Ceratitis capitata, Dacus oleae, Tipula paludosa, Hylemyia spp., Liriomyza 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.,
  • the compounds according to the invention can also be used in certain concentrations or application rates as herbicides and microbicides, for example as fungicides, antifungal agents and bactericides. You leave may also be used as intermediates or products for the synthesis of other active ingredients.
  • 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 which can be obtained by conventional breeding and optimization methods or by biotechnological and genetic engineering methods or combinations of these methods, including the transgenic plants and including the plant cultivars which can or cannot be protected by plant breeders' rights.
  • Plant parts are to be understood to mean all above-ground and underground parts and organs of plants, such as shoots, leaves, flowers and roots, examples being leaves, needles, stems, stems, flowers, fruiting bodies, fruits and seeds, and roots, tubers and rhizomes.
  • the plant parts also include crops and vegetative and generative propagation material, for example cuttings, tubers, rhizomes, offshoots and seeds.
  • Storage room 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 multi-layer coating.
  • the active compounds can be converted into the customary formulations, such as solutions, emulsions, wettable powders, suspensions, powders, dusts, pastes, soluble powders, granules, suspension emulsion concentrates, active substance-impregnated natural and synthetic substances and very fine encapsulations in polymeric substances.
  • formulations are prepared in a known manner, for example by mixing the active ingredients with extenders, that is to say liquid solvents and / or solids Carriers, where appropriate using surface-active agents, that is to say emulsifiers and / or dispersants and / or foam-generating agents.
  • water is used as an extender, e.g. also organic
  • Solvents are used as auxiliary solvents.
  • the following are essentially suitable as liquid 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 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.
  • ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone
  • strongly polar solvents such as dimethylformamide and dimethyl sulfoxide
  • Ammonium salts and natural rock powders such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and synthetic rock powders such as highly disperse silica, aluminum oxide and silicates are suitable as solid carriers for granules: e.g. broken and fractionated natural rocks such as calcite, marble, pumice, sepiolite, dolomite and synthetic granules from inorganic and organic flours 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 powdery, granular or latex-shaped polymers can be used in the formulations, 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, 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
  • Active ingredient preferably between 0.5 and 90%.
  • the active compounds according to the invention can be used as such or in their formulations, also in a mixture with known fungicides, bactericides, acaricides, nematicides or insecticides, in order, for example, to to spread the spectrum of activity or to prevent the development of resistance.
  • synergistic effects are obtained, i.e. the effectiveness of the mixture is greater than the effectiveness of the individual components.
  • Famoxadon Fenapanil, Fenarimol, Fenbuconazol, Fenfuram, Fenitropan, Fenpiclonil, Fenpropidin, Fenpropimo ⁇ h, Fentinacetat, Fentinhydroxyd, Ferbam, Ferimzon, Fluazinam, Flumetover, Fluoromid, Fluquinconazol, Flu ⁇ rimidol, Flusrimidol, Flusrilidol, Flusrilidol, Flusrilidol, Flusrilidol, Flusrilidol, Flusrilidol, Flusrilidol, Flusrilidol, Flusrilidol, Flusrilidol, Flusrilidol, Flusrilidol, Flusrilidol, Fosetyl sodium, fthalide, fuberidazole, furalaxyl, furametpyr, furcarbonil, furconazole,
  • Imazalil Imibenconazol, Iminoctadin, Iminoctadinealbesilat, Iminoctadinetriacetat, Iodocarb, Ipconazol, Iprobefos (IBP), Iprodione, rrumamycin, Isoprothiolan, Isovaledione,
  • 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, Meth tartroxam, Metiram, Metomeclam, Metsulfovax, Mildiomycin, Myclobutanil, Myclozolin,
  • Paclobutrazole pefurazoate, penconazole, pencycuron, phosdiphen, picoxystrobin, pimaricin, piperalin, polyoxin, polyoxorim, probenazole, prochloraz, procymidone,
  • Tebuconazole Tebuconazole, tecloftalam, tecnazen, tetcyclacis, tetraconazole, thiabendazole, thicyofen, thifluzamide, thiophanate-methyl, thiram, dioxymid, tolclofos-methyl, tolylfluanid, triadimefon, triadimenol, triazbutichl, triazoxid, triazoxid, triazoxide, triazoxide
  • Tridemo ⁇ h trifloxystrobin, triflumizole, triforin, triticonazole, uniconazole,
  • N-formyl-N-hydroxy-DL-alanine sodium salt O, O-diethyl- [2- (dipropylamino) -2-oxoethyl] ethylphosphoramidothioate, O-methyl-S-phenyl-phenylpropylphosphoramidothioate, S-methyl-1, 2,3-benzothiadiazole-7-carbothioate, spiro [2H] -l-Benzopyran-2, r (3 ⁇ ) -isobenzofuran] -3'-one, 4- [3, 4-dimethoxyphenyl) -3 - (4-fluo ⁇ henyl) acryloyl] -mo ⁇ holin
  • Cadusafos Carbaryl, Carbofuran, Carbophenothion, Carbosulfan, Cartap, Chloethocarb, Chlorethoxyfos, Chlorfenapyr, Chlorfenvinphos, Chlorfluazuron, Chlormephos, Chlo ⁇ yrifos, Chlo ⁇ yrifos M, Chlovaporthrin, Chromafenozide, Cis-
  • Fenamiphos Fenazaquin, Fenbutatin oxide, Fenitrothion, Fenothiocarb, Fenoxacrim, Fenoxycarb, Fenpropathrin, Fenpyrad, Fenpyrithrin, Fenpyroximate, Fenvalerate, Fipronil, Fluazinam, Fluazuron, Flubrocythrinate, Flucycloxuron, Flucythrin
  • Flufenoxuron Flumethrin, Flutenzine, Fluvalinate, Fonophos, Fosmethilan, Fosthiazate, Fubfenprox, Furathiocarb,
  • Halofenozide HCH, Heptenophos, Hexaflumuron, Hexythiazox, Hydroprene,
  • Methoxyfenozide metolcarb, metoxadiazone, mevinphos, milbemectin, milbemycin, monocrotophos,
  • 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 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.
  • plants and their parts can be treated according to the invention.
  • plant species and plant cultivars 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 (genetic modified organisms) and their parts are treated.
  • the term "parts” or “parts of plants” or “plant parts” was explained above.
  • Plants of the plant varieties which are in each case commercially available or in use are particularly preferably treated according to the invention.
  • plant varieties plants are understood to have new properties ("traits") which have been grown by conventional breeding, by mutagenesis or by recombinant DNA techniques. These can be varieties, bio and genotypes.
  • the treatment according to the invention can also cause superadditive ("synergistic") effects. For example, reduced application rates and / or widening of the activity spectrum and / or an increase in the action of the substances and agents which can be used according to the invention, better plant growth, are increased
  • transgenic plants or plant cultivars to be treated according to the invention include all plants which, by virtue of the genetic engineering modification, received genetic material which contained them
  • traits are better plant growth, increased tolerance to high or low temperatures, increased tolerance to drought or to water or soil salt content, increased flowering performance, easier harvesting, accelerated ripening, higher crop yields, higher quality and / or higher
  • Nutritional value of the harvested products higher shelf life and / or workability of the harvested products. Further and particularly highlighted examples of such properties are an 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.
  • the important ones are examples of transgenic plants Cultivated plants such as cereals (wheat, rice), corn, soybeans, potatoes, cotton, rapeseed and fruit plants (with the fruits apples, pears, citrus fruits and grapes) are mentioned, with corn, soybeans, potatoes, cotton and rapeseed being particularly emphasized.
  • the properties (“traits”) are particularly emphasized of the plants' increased defense 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), Cry ⁇ A (b ), Cry ⁇ A (c), CryDA, CrylllA, CryDIB2, Cry9c, Cry2Ab, Cry3Bb and CrylF as well as their combinations) are generated in the plants (hereinafter “Bt plants”).
  • the properties (“traits”) also particularly emphasize the increased defense of plants against fungi, bacteria and viruses by systemic acquired resistance (SAR), systemin, phytoalexins, elicitors and resistance genes and correspondingly expressed proteins and toxins.
  • the properties (“traits”) which are furthermore particularly emphasized are the increased tolerance of the plants to certain herbicidal active compounds, for example imidazolinones, sulfonylureas, glyphosate or
  • Phosphinotricin e.g. "PAT” gene
  • the genes imparting the desired properties (“traits”) can also occur in combinations with one another in the transgenic plants.
  • “Bt plants” include corn, cotton, soy and potato, which are sold 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 sold under the trade names Roundup Ready® (tolerance to glyphosate e.g. corn, cotton, soy), Liberty Link® (tolerance to phosphinotricin, e.g. rapeseed),
  • the herbicide-resistant plants include the varieties sold under the name Clearfield® (eg maize). Of course, these statements also apply to those developed in the future or to the market in the future upcoming plant varieties with these or future developed genetic traits.
  • plants listed can be treated particularly advantageously according to the invention with the compounds of the general formula I or the active compound mixtures according to the invention.
  • the preferred ranges given above for the active substances or mixtures also apply to the treatment of these plants.
  • Plant treatment with the compounds or mixtures specifically listed in the present text should be particularly emphasized.
  • the active compounds 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, mites, running mites, flies (stinging and licking), parasitic fly larvae, lice, hair lice, Featherlings and fleas.
  • animal parasites ectoparasites
  • tick ticks leather ticks
  • mites running mites
  • flies stinging and licking
  • parasitic fly larvae lice, hair lice, Featherlings and fleas.
  • Anoplurida e.g. Haematopinus spp., Linognathus spp., Pediculus spp., Phtirus spp., Solenopotes spp ..
  • Ischnocerina e.g. Trimenopon spp., Menopon spp., Trinoton spp., Bovicola spp., Werneckiella spp., Lepikentron spp., Damalina spp., Trichodectes spp., Felicola spp ..
  • Nematocerina and Brachycerina e.g. Aedes spp., Anopheles spp., Culex spp., Simulium 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., Hypodectolich spp., Pod ., Psoroptes spp., Chorioptes spp., Otodectes spp., Sarcoptes spp., Notoedres spp., Knemidocoptes spp., Cytodites spp., Laminosioptes spp ..
  • the active compounds of the formula (I) according to the invention are also suitable for controlling arthropods which are used in agricultural animals, e.g. Cattle, sheep, goats,
  • the active compounds according to the invention are used in the veterinary sector in a known manner by enteral administration in the form of, for example, tablets,
  • formulations for example powders, emulsions, flowable agents
  • active compounds in an amount of 1 to 80% by weight, directly or after 100 to 10,000 times dilution, or use them as a chemical bath.
  • insects may be mentioned by way of example and preferably, but without limitation:
  • Hymenoptera such as Sirex juvencus, Urocerus gigas, Urocerus gigas taignus, Urocerus augur.
  • Kalotermes flavicollis Cryptotermes brevis, Heterotermes indicola, Reticulitermes flavipes, Reticulitermes santonensis, Reticulitermes lucifugus, Mastotermes darwiniensis, Zootermopsis 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,
  • the active substances can be used as such, in the form of concentrates or generally customary formulations such as powders, granules, solutions, suspensions, emulsions or pastes.
  • the formulations mentioned can be prepared in a manner known per se, e.g. by mixing the active ingredients with at least one solvent or diluent, emulsifier, dispersant and / or binder or fixative, water repellent, optionally siccatives and UV stabilizers and optionally dyes and pigments and further processing aids.
  • the insecticidal compositions or concentrates used to protect wood and wood-based materials contain the active compound 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 optimal amount 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 compound, based on the material to be protected.
  • organic-chemical solvent or solvent mixture and / or an oily or oily or low-volatility organic-chemical solvent or solvent mixture and / or a polar organic-chemical solvent or solvent mixture and / or water and optionally an emulsifier and / or wetting agents.
  • the organic chemical solvents used are preferably oily or oily ones
  • Corresponding mineral oils are such low-volatility, water-insoluble, oily and oily solvents or their aromatic fractions or mineral oil-containing solvent mixtures, preferably white spirit, petroleum and / or alkylbenzene.
  • Mineral oils with a boiling range of 170 to 220 ° C, test gasoline with a boiling range of 170 to 220 ° C, spindle oil with a boiling range of 250 to 350 ° C, petroleum or aromatics with a boiling range of 160 to 280 ° C are advantageous. Te ⁇ entinöl and the like. For use.
  • Evaporation rate above 35 and a flash point above 30 ° C, preferably above 45 ° C can be partially replaced by volatile or moderately volatile organic chemical solvents, provided that the solvent mixture also has an evaporation number above 35 and a flash point above 30 ° C, preferably above 45 ° C, and that the insecticide fungicide
  • part of the organic chemical solvent or solvent mixture or an aliphatic polar organic chemical solvent or solvent mixture is replaced.
  • Aliphatic organic chemical solvents containing hydroxyl and / or ester and / or ether groups, such as, for example, glycol ethers, esters or the like, are preferably used.
  • the known water-thinnable and / or in the used organic-chemical binders organochemical solvents soluble or dispersible or emulsifiable synthetic resins and / or binding drying oils, in particular binders consisting of or containing an acrylate resin, a vinyl resin, for example polyvinyl acetate, polyester resin, polycondensation or polyaddition resin, polyurethane resin, alkyd resin or modified alkyd resin, phenolic resin , Hydrocarbon resin such as inden-coumarone resin, silicone resin, drying vegetable and / or drying oils and / or physically drying binders based on a natural and / or synthetic resin.
  • binders consisting of or containing an acrylate resin, a vinyl resin, for example polyvinyl acetate, polyester resin, polycondensation or polyaddition resin, polyurethane resin, alkyd resin or modified alkyd resin, phenolic resin , Hydrocarbon resin such as inden-coumarone resin, silicone resin, drying
  • the synthetic resin used as a binder can be used in the form of an emulsion, dispersion or solution. Bitumen or bituminous substances up to 10% by weight can also be used as binders. In addition, known dyes, pigments, water-repellants, odor correctors and inhibitors or anticorrosive agents and the like can be used.
  • At least one alkyd resin or modified alkyd resin and / or a drying vegetable oil is preferably contained in the agent or in the concentrate as the organic chemical binder.
  • Alkyd resins with an oil content of more than 45% by weight, preferably 50 to 68% by weight, are preferably used according to the invention.
  • binder All or part of the binder mentioned can be replaced by a fixing agent (mixture) or a plasticizer (mixture). These additives are intended to prevent volatilization of the active ingredients and crystallization or precipitation. They preferably replace 0.01 to 30% of the binder (based on
  • the plasticizers come from the chemical classes of phthalic acid esters such as
  • 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, glycerol ether or higher molecular weight glycol ether, glycerol ester
  • Fixing agents are chemically based on polyvinyl alkyl ethers such as e.g. Polyvinyl methyl ether or ketones such as benzophenone, ethylene benzophenone.
  • Water is also particularly suitable as a solvent or diluent, if appropriate in a mixture with one or more of the above-mentioned organic chemical solvents or diluents, emulsifiers and dispersants.
  • a particularly effective wood protection is achieved through industrial impregnation processes, e.g. Vacuum, double vacuum or pressure process.
  • the ready-to-use compositions can optionally contain further insecticides and, if appropriate, one or more fungicides.
  • insecticides and fungicides mentioned in WO 94/29 268 are preferably suitable as additional admixing partners.
  • the compounds mentioned in this document are an integral part of the present application.
  • Insecticides such as chloropyriphos, phoxim, silafluofm, alphamethrin, cyfluthrin, cypermethrin, deltamethrin, permethrin, imidacloprid, NI-25, flufenoxuron, hexaflumuron, transfluthronium, methifluoropuron, methifluoropuron, thifluoropuron, methifluoropuron
  • the compounds according to the invention can be used to protect objects, in particular ship hulls, sieves, nets, structures, quay systems and signaling systems which come into contact with sea or brackish water.
  • heavy metals such as e.g. in bis- (trialkyltin) sulfide, tri-n-butyltin laurate, tri-n-butyltin chloride, copper (I) oxide, triethyltin chloride, tri - «- butyl (2-phenyl-4-chl ⁇ henoxy) tin, tributyltin oxide,
  • Tributyltin halides are omitted or the concentration of these Connections are significantly reduced.
  • the ready-to-use antifouling paints may also contain other active ingredients, preferably algicides, fungicides, herbicides, molluscicides or other antifouling active ingredients.
  • Suitable combination partners for the antifouling agents according to the invention are preferably:
  • Fentin acetate, metaldehyde, methiocarb, niclosamide, thiodicarb and trimethacarb; or conventional antifouling agents 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 from 0.01 to 20% by weight.
  • the antifouling agents according to the invention furthermore contain the usual constituents, e.g. in Ungerer, Chem. Ind. 1985, 37, 730-732 and Williams, Antifouling Marine Coatings, Noyes, Park Ridge, 1973.
  • Antifouling paints contain, in addition to the algicidal, fungicidal, moUuscicidal and insecticidal active compounds according to the invention, in particular binders.
  • Examples of recognized binders are polyvinyl chloride in a solvent system, chlorinated rubber in a solvent system, acrylic resins in a solvent system, in particular in an aqueous system, vinyl chloride / vinyl acetate copolymer systems in the form of aqueous dispersions or in the form of organic solvent systems, butadiene / styrene / acrylonitrile Rubbers, drying oils such as linseed oil, resin esters or modified hard resins in combination with tar or bitumen, asphalt and epoxy compounds, small amounts of chlorinated rubber, chlorinated polypropylene and vinyl resins.
  • Paints may also contain inorganic pigments, organic pigments or dyes, which are preferably insoluble in sea water. Paints may also contain materials such as rosin to enable controlled release of the active ingredients. The paints may also contain plasticizers, modifiers affecting theological properties, and other conventional ingredients.
  • the compounds according to the invention or those mentioned above can also be used in self-polishing antifouling systems
  • the active ingredients are also suitable for controlling animal pests, in particular insects, arachnids and mites, which live in closed spaces such as apartments, factory halls, offices, vehicle cabins, etc. occurrence.
  • Sco ⁇ ionidea e.g. Buthus occitanus.
  • Acarina e.g. Argas persicus, Argas reflexus, Bryobia ssp., Dermanyssus gallinae, Glyciphagus domesticus, Omithodorus moubat, Rhipicephalus sanguineus, Trombicula alfreddugesi, Neutrombicula auturnnalis, Dermatophagoides pteronissimus, Dermatophagoides forinae.
  • Opiliones e.g. Pseudosco ⁇ iones chelifer, Pseudosco ⁇ iones cheiridium, Opiliones phalangium.
  • Diplopoda e.g. Blaniulus guttulatus, Polydesmus spp.
  • Saltatoria for example Acheta domesticus.
  • Dermaptera for example, Forficula auricularia.
  • Lepidoptera e.g. Achroia grisella, Galleria mellonella, Plodia inte ⁇ unctella, Tinea cloacella, Tinea pellionella, Tineola bisselliella.
  • Ctenocephalides canis Ctenocephalides felis, Pulex irritans, Tunga penetrans, Xenopsylla cheopis.
  • Hymenoptera e.g. Campono tus herculeanus, Lasius fuliginosus, Lasius niger, Lasius umbratus, Monomorium pharaonis, Paravespula spp., Tetramorium caespitum.
  • Pediculus humanus capitis for example Pediculus humanus capitis, Pediculus humanus co ⁇ oris, Phthirus pubis.
  • Heteroptera for example Cimex hemipterus, Cimex lectularius, Rhodinus prolixus, Triatoma infestans.
  • the product precipitates as an oil
  • the water is decanted off, the oil is dissolved in 10 ml of MeOH and either in the refrigerator or in
  • the product from methanol usually precipitates as a solid within 1 - 2 days.
  • the nitrating acid is prepared from 400 ml 65 percent. HNO 3 and 120 ml conc. H 3 PO 4 , enter them in a 1 1 two-necked flask with a KPG stirrer, reflux condenser and dropping funnel and heat them to 100 - 105 ° C while stirring (the oil bath temperature must not exceed 115 ° C ). 230 g of l-bromo-l, 4,4-trichloro-l, 3-butadiene are then added dropwise to the nitrating acid in the course of 2 h and the mixture obtained is stirred still 1 h at 110 - 115 ° C oil bath temperature.
  • the nitrating acid is prepared from 200 ml 65 percent. ENT 3 and 65 ml 98 percent. H 2 SO 4 , enter it in a 0.5 1 two-necked flask with a KPG stirrer, reflux condenser and dropping funnel and heat it to 95 - 100 ° C while stirring (the oil bath temperature must not exceed 110 ° C). Then 136 g of Z, El-bromo-l, 2,4,4-trichloro-l, 3-butadiene are added dropwise to the nitrating acid within 2 h and the mixture obtained is stirred for a further 3 h at 100-105 ° C. oil bath temperature. After cooling to room temperature, the organic layer is separated off, the aqueous phase is extracted with chloroform, and the combined organic phases are washed with water, 5 percent. NaHCO 3 -
  • the first fraction (approx. 4 - 8% of the total amount) is distilled off bromodichloracrolein.
  • the main fraction consists of 71 g of Z, E-4-bromo-2-nitro-l, l, 3,4-tetrachlor-l, 3-butadiene, yield 45%.
  • Ether is added at room temperature to 4.72 g (38 mmol) of 4-methylthiophenol and stirred for 20 h. Then the ⁇ ther i.Vak. deducted and that after the addition of 20 ml
  • Solvent 7 parts by weight of dimethylformamide emulsifier: 2 parts by weight of alkylaryl polyglycol ether
  • active compound 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration.
  • Field bean seedlings (Vicia faba minor), which are infested with the green peach aphid (Myzus persicae), are immersed in a preparation of active compound of the desired concentration and placed in a plastic can.
  • the kill is determined in%. 100% means that all animals have been killed; 0% means that no animals have been killed.
  • Emulsifier 1 part by weight of alkylaryl polyglycol ether
  • active compound 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with water containing emulsifier 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 larvae of the horseradish beetle (Phaedon cochleariae) while the leaves are still moist.
  • the kill is determined in%. 100% means that all beetle larvae have been killed; 0% means that no beetle larvae have been killed.
  • Solvent 100 parts by weight of acetone 1900 parts by weight of methanol
  • a specified amount of active compound preparation of the desired concentration is pipetted onto a standardized amount of synthetic feed. After the methanol has evaporated, approx. 200-300 eggs of the cockroach (Plutella xylostella) are added to the feed.
  • the death of the eggs or larvae is determined in%. 100% means that all animals have been killed; 0% means that no animals have been killed.
  • Emulsifier 2 parts by weight of alkylaryl polyglycol ether
  • Cotton leaves which are heavily infested with the cotton aphid (Aphis gossypii), are treated by immersing them in the active ingredient preparation of the desired concentration.
  • the kill is determined in%. 100% means that all aphids have been killed; 0% means that no aphids have been killed.
  • Test insect Aphis gossypii
  • Emulsifier 1 part by weight of alkylaryl polyglycol ether
  • Amount of emulsifier and dilute the concentrate with water to the desired concentration is required.
  • the active ingredient preparation is poured onto the bottom of the infected savoy plant.
  • the active ingredient can be taken up from the soil by the plant roots and transported to the leaves.
  • the concentration of the active ingredient in the preparation is practically irrelevant, the only decisive factor is the amount of active ingredient per unit volume of soil, which is given in ppm (mg / ml).
  • the root systemic effect of the active ingredient is derived from the kill numbers. It is 100% when all test animals have been killed and 0% when as many test insects are still alive as in the untreated control.
  • Test insect Myzus persicae
  • Emulsifier 1 part by weight of alkylaryl polyglycol ether
  • active compound 1 part by weight of active compound is mixed with the stated amount of solvent, the stated amount of emulsifier is added and the concentrate is diluted with water to the desired concentration.
  • the active ingredient preparation is poured onto the soil of the infected savoy plant.
  • the active ingredient can be taken up from the soil by the plant roots and transported to the leaves.
  • the concentration of the active ingredient in the preparation is practically irrelevant.
  • the decisive factor is the amount of active ingredient per unit volume of soil, which is given in ppm (mg / ml).
  • the root systemic effect of the active ingredient is derived from the kill numbers. It is 100% when all test animals have been killed and 0% when as many test insects are still alive as in the untreated control.
  • Solvent 7 parts by weight of dimethylformamide emulsifier: 2 parts by weight of alkylaryl polyglycol ether
  • active compound 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted to the desired concentration with water containing emulsifier.
  • Cabbage leaves (Brassica oleracea), which are heavily infested with the green peach aphid (Myzus persicae), are treated by immersing them in the active ingredient preparation of the desired concentration.
  • the kill is determined in%. 100% means that all aphids have been killed; 0% means that no aphids have been killed.
  • Emulsifier 2 parts by weight of alkylaryl polyglycol ether
  • Cabbage leaves (Brassica oleracea) are treated by being dipped into the preparation of active compound of the desired concentration and populated with larvae of the horseradish leaf beetle (Phaedon cochleariae) while the leaves are still moist.
  • the kill is determined in%. 100% means that all beetle larvae have been killed; 0% means that no beetle larvae have been killed.
  • Solvent 7 parts by weight of dimethylformamide emulsifier: 2 parts by weight of alkylaryl polyglycol ether
  • active compound 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier and the concentrate is diluted with water to the desired concentrations.
  • Cotton plants which are infested with eggs, larvae and pupas of the whitefly (Bemisia tabaci), are immersed in an active ingredient preparation of the desired concentration.
  • the kill is determined in%. 100% means that all animals have been killed; 0% means that no animals have been killed.
  • Emulsifier 2 parts by weight of alkylaryl polyglycol ether
  • active compound 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted to the desired concentration with water containing emulsifier.
  • Cabbage leaves (Brassica oleracea) are treated by being dipped into the preparation of active compound of the desired concentration and populated with caterpillars of the army worm (Spodoptera frugiperda) 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.
  • Test insect Myzus persicae
  • Emulsifier 1 part by weight of alkylaryl polyglycol ether
  • active compound 1 part by weight of active compound is mixed with the stated amount of solvent, the stated amount of emulsifier is added and the concentrate is diluted with water to the desired concentration.
  • the active ingredient preparation is intimately mixed with the soil. The plays
  • Concentration of the active ingredient in the preparation is practically irrelevant, the only decisive factor is the amount of active ingredient per unit volume of soil, which is given in ppm (mg / ml).
  • the treated soil is filled in 250 ml pots and these pre-germinated field beans are planted.
  • the active ingredient can be taken up from the soil by the plant roots and transported to the leaves.
  • the plants are populated with the test animals mentioned above after 7 days and after a further 7 days the evaluation is carried out by counting or estimating the dead animals.
  • the root systemic effect of the active ingredient is derived from the kill numbers. It is 100% when all test animals have been killed and 0% when as many test insects are still alive as in the untreated control.
  • Active ingredients Active ingredient concentration in 4 ppm% kill after weeks
  • Test animals adults of Ctenocephalides felis solvent: dimethyl sulfoxide (DMSO)
  • a suitable active ingredient solution is prepared from 20 mg of active ingredient with 1 ml of DMSO. 15 ⁇ l of this formulation are added to 3 ml of citrated bovine blood and stirred.
  • Blood is heated to 37 ° C, a temperature of 25 ° C is set in the area of the flea chambers. Controls are mixed with the same volume of DMSO without adding a compound. Triple determinations are carried out.
  • Test animals adult Musca domestica, Reichswald strain (OP, SP, carbamate-resistant)
  • the effectiveness of the active ingredient preparation is determined. 100% means that all flies have been killed; 0% means that no flies have been killed.
  • Test animals Lucilia cuprina larvae
  • Solvent dimethyl sulfoxide
  • test tubes are removed for 2 days and the dolls are counted.
  • the effect of the active substance preparation is assessed according to the number of flies hatched after 1.5 times the development time of an untreated control. 100% means that no flies have hatched; 0% means that all flies hatched normally.

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)
  • Plural Heterocyclic Compounds (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

La présente invention concerne de nouveaux nitrobutadiènes halogénés, leur procédé de production et leur utilisation dans la lutte contre les parasites animaux.
EP02777324A 2001-11-05 2002-10-23 Nitrobutadienes halogenes servant a lutter contre les parasites animaux Withdrawn EP1444221A1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE10154313A DE10154313A1 (de) 2001-11-05 2001-11-05 Halogen-nitro-butadiene
DE10154313 2001-11-05
PCT/EP2002/011844 WO2003040129A1 (fr) 2001-11-05 2002-10-23 Nitrobutadienes halogenes servant a lutter contre les parasites animaux

Publications (1)

Publication Number Publication Date
EP1444221A1 true EP1444221A1 (fr) 2004-08-11

Family

ID=7704691

Family Applications (1)

Application Number Title Priority Date Filing Date
EP02777324A Withdrawn EP1444221A1 (fr) 2001-11-05 2002-10-23 Nitrobutadienes halogenes servant a lutter contre les parasites animaux

Country Status (9)

Country Link
US (1) US7332512B2 (fr)
EP (1) EP1444221A1 (fr)
JP (1) JP4373784B2 (fr)
KR (1) KR100926514B1 (fr)
CN (1) CN100338057C (fr)
BR (1) BR0213898A (fr)
DE (1) DE10154313A1 (fr)
TW (1) TW200304771A (fr)
WO (1) WO2003040129A1 (fr)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR100836172B1 (ko) * 2007-07-26 2008-06-09 한국생명공학연구원 아졸계 화합물을 유효성분으로 하는 살충제 조성물
EP2382865A1 (fr) * 2010-04-28 2011-11-02 Bayer CropScience AG Combinaisons d'agents actifs synergiques
CN103450175B (zh) * 2013-08-12 2016-03-02 湖北省生物农药工程研究中心 共轭双烯衍生物及其制备方法和作为抗癌药物的用途
CN110256404B (zh) * 2019-04-30 2025-05-27 华东理工大学 具有杀虫活性的双烯化合物、其制备及用途

Family Cites Families (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
ZW5085A1 (en) 1984-04-13 1985-09-18 Nihon Tokushu Noyaku Seizo Kk Nitromethylene derivatives,intermediates thereof,processes for production thereof,and insecticides
US5204360A (en) 1985-02-04 1993-04-20 Nihon Bayer Agrochem K.K. Heterocyclic compounds
US5001138B1 (en) 1985-02-04 1998-01-20 Bayer Agrochem Kk Heterocyclic compounds
ATE67493T1 (de) 1985-02-04 1991-10-15 Bayer Agrochem Kk Heterocyclische verbindungen.
DE3717837A1 (de) 1987-05-27 1988-12-08 Bayer Ag Heterocyclisch substituierte 2-(1'-nitroalkyliden)-1,3-heterocyclen
GB8927277D0 (en) 1989-12-01 1990-01-31 Glaxo Group Ltd Chemical compounds
DE4028047A1 (de) 1990-09-05 1992-03-12 Bayer Ag Verfahren zur herstellung von n-(2-chlor-pyridin-5-yl-methyl)-ethylendiamin
DE4137271A1 (de) 1991-11-13 1993-05-19 Bayer Ag Verfahren zur herstellung von n-(2-chlor-pyridin-5-yl-methyl)-ethylendiamin
JPH0672138B2 (ja) 1992-01-31 1994-09-14 日本バイエルアグロケム株式会社 新規アミノアルカンチオール類及びその製法
JP3149989B2 (ja) 1992-04-28 2001-03-26 広栄化学工業株式会社 ２−クロロ−５−置換アミノメチルピリジン類の製法
JPH0616636A (ja) 1992-06-30 1994-01-25 Ishihara Sangyo Kaisha Ltd ６−クロロ−３−ピリジルメチルアミン類の製造方法
ES2114623T3 (es) 1993-02-01 1998-06-01 Koei Chemical Co Procedimiento para preparar 2-cloro-5-aminometil-piridinas.
WO1994029268A1 (fr) 1993-06-07 1994-12-22 Bayer Aktiengesellschaft Iodopropargylcarbamates et leur utilisation comme biocides pour la protection des vegetaux et des materiaux
JPH07242633A (ja) 1994-03-03 1995-09-19 Ishihara Sangyo Kaisha Ltd ５−アミノエチルアミノメチル−２−クロロピリジンの製造方法
DE19548872A1 (de) 1995-12-27 1997-07-03 Bayer Ag Synergistische insektizide Mischungen

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO03040129A1 *

Also Published As

Publication number Publication date
US7332512B2 (en) 2008-02-19
CN100338057C (zh) 2007-09-19
KR20050039693A (ko) 2005-04-29
DE10154313A1 (de) 2003-05-15
WO2003040129A1 (fr) 2003-05-15
KR100926514B1 (ko) 2009-11-12
US20050080272A1 (en) 2005-04-14
TW200304771A (en) 2003-10-16
BR0213898A (pt) 2004-08-31
JP2005518348A (ja) 2005-06-23
JP4373784B2 (ja) 2009-11-25
CN1610677A (zh) 2005-04-27

Similar Documents

Publication Publication Date Title
EP1363905A1 (fr) Pyrazolylpyrimidines
EP1429607A1 (fr) Delta 1-pyrrolines utilisees comme pesticides
EP1367893A1 (fr) Pyridylpyrimidines en tant qu'agents de lutte contre les parasites
EP1359803B1 (fr) Melanges synergiques de pesticides contre les parasites animaux
DE10034130A1 (de) Heterocyclische Fluoralkenylthioether (lV)
EP1360190A1 (fr) Diamide d'acide phtalique, son procede de fabrication et son utilisation comme pesticide
EP1383773A2 (fr) Azoles a effet insecticide
EP1474389A2 (fr) Delta1-pyrrolines
EP1289969A1 (fr) N-benzoyl-n'-(tetrazolylphenyl)-urees substituees et leur utilisation comme produits antiparasitaires
DE10204116A1 (de) DELTA·1·-Pyrroline
DE10034132A1 (de) Heterocyclische Fluoralkenylthioether (lll)
DE10034131A1 (de) Heterocyclische Fluoralkenylthioether (II)
DE10034133A1 (de) Heterocyclische Fluoralkenylthioether (l)
EP1444221A1 (fr) Nitrobutadienes halogenes servant a lutter contre les parasites animaux
EP1414815A1 (fr) Derives de tetrahydropyridazine et leur utilisation comme pesticides
EP1412334A1 (fr) Derives de pyrazoline et leur utilisation comme agents de lutte contre les parasites
EP1474418A1 (fr) 4-hetaryl-pyrazolines substituees servant d'agent de lutte contre des parasites
DE10119421A1 (de) Insektizide Mittel
DE10201544A1 (de) Substituierte Pyrazoline
DE10134720A1 (de) Synergistische Mischungen
EP1399421A1 (fr) Imidates substitues utilises en tant que produits de lutte contre les parasites
DE10115406A1 (de) Phthalsäurediamide
DE10206791A1 (de) Substituierte 4-Pyrazolyl-pyrazoline
DE10139721A1 (de) Oxadiazolyl- u. Thiadiazolyl-benzoylharnstoffe
WO2003040092A2 (fr) $g(d)1-pyrrolines

Legal Events

Date Code Title Description
PUAI Public reference made under article 153(3) epc to a published international application that has entered the european phase

Free format text: ORIGINAL CODE: 0009012

17P Request for examination filed

Effective date: 20040607

AK Designated contracting states

Kind code of ref document: A1

Designated state(s): AT BE BG CH CY CZ DE DK EE ES FI FR GB GR IE IT LI LU MC NL PT SE SK TR

AX Request for extension of the european patent

Extension state: AL LT LV MK RO SI

17Q First examination report despatched

Effective date: 20070910

STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: THE APPLICATION IS DEEMED TO BE WITHDRAWN

18D Application deemed to be withdrawn

Effective date: 20110503