Classifications

• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
  • C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
  • C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
  • C07D307/79—Benzo [b] furans; Hydrogenated benzo [b] furans with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
  • C07D307/81—Radicals substituted by nitrogen atoms not forming part of a nitro radical
• • A—HUMAN NECESSITIES
  • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
  • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
  • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
  • A01N47/40—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having a double or triple bond to nitrogen, e.g. cyanates, cyanamides
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C261/00—Derivatives of cyanic acid
  • C07C261/04—Cyanamides
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C317/00—Sulfones; Sulfoxides
  • C07C317/44—Sulfones; Sulfoxides having sulfone or sulfoxide groups and carboxyl groups bound to the same carbon skeleton
  • C07C317/46—Sulfones; Sulfoxides having sulfone or sulfoxide groups and carboxyl groups bound to the same carbon skeleton the carbon skeleton being further substituted by singly-bound oxygen atoms
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
  • C07C323/23—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
  • C07C323/39—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton at least one of the nitrogen atoms being part of any of the groups, X being a hetero atom, Y being any atom
  • C07C323/40—Y being a hydrogen or a carbon atom
  • C07C323/41—Y being a hydrogen or an acyclic carbon atom
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
  • C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
  • C07D277/62—Benzothiazoles
  • C07D277/64—Benzothiazoles with only hydrocarbon or substituted hydrocarbon radicals attached in position 2
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D313/00—Heterocyclic compounds containing rings of more than six members having one oxygen atom as the only ring hetero atom
  • C07D313/02—Seven-membered rings
  • C07D313/06—Seven-membered rings condensed with carbocyclic rings or ring systems
  • C07D313/10—Seven-membered rings condensed with carbocyclic rings or ring systems condensed with two six-membered rings
  • C07D313/12—[b,e]-condensed
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
  • C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
  • C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
  • C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
  • C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
  • C07D317/50—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to atoms of the carbocyclic ring
  • C07D317/58—Radicals substituted by nitrogen atoms
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D321/00—Heterocyclic compounds containing rings having two oxygen atoms as the only ring hetero atoms, not provided for by groups C07D317/00 - C07D319/00
  • C07D321/12—Eight-membered rings
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
  • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
  • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
  • C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
  • C07D333/14—Radicals substituted by singly bound hetero atoms other than halogen
  • C07D333/20—Radicals substituted by singly bound hetero atoms other than halogen by nitrogen atoms
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
  • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
  • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
  • C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur 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
  • C07D333/28—Halogen atoms

Definitions

• the present application relates to new imidamide derivatives, a process for their preparation and their use for controlling animal pests.
• R represents cyano or nitro
• R 1 represents hydrogen, optionally substituted alkyl, optionally substituted cycloalkyl or optionally substituted phenyl,
• R 2 represents hydrogen, optionally substituted alkyl or optionally substituted cycloalkyl
• R 5 where R 4 and R 5 independently of one another represent hydrogen, optionally substituted alkyl or optionally substituted cycloalkyl,
• R 6 and R 7 independently of one another represent optionally substituted aryl, optionally substituted cycloalkyl or an optionally substituted mono- or bicyclic, nitrogen-free heterocycle,
• R 8 represents alkyl or optionally substituted aryl
• Alk stands for alkyl
• a and A 'independently of one another represent straight-chain or branched alkanediyl and
• the imidamide derivatives of the formula (I) can also occur as optical and / or geometric isomers, depending on the substituents.
• the present invention relates both to the various isomer mixtures and to the pure isomers.
• R - N C - Q - Z
• R 2 and R 3 have the meaning given above
• the new imidamide derivatives of the general formula (I) have highly pronounced biological properties and are primarily for combating animal pests, such as insects, arachnids and in particular nematodes, which are used in agriculture, in the forestry, in the protection of stocks and materials occur in the hygiene sector.
• R preferably represents cyano or nitro.
• R 1 preferably represents hydrogen, C 1 -C 4 -alkyl which is optionally substituted by halogen, cyano or C ] -C 4 -alkoxy, optionally optionally bis trisubstituted by identical or different manner by halogen or C j -C ⁇ alkyl-substituted C 3 -C 6 cycloalkyl, or represents optionally mono- to trisubstituted by identical or different phenyl, suitable substituents being the phenyl substituents mentioned under R 6 are suitable.
• R 2 preferably represents hydrogen, C1-C4-alkyl which is optionally substituted by halogen, cyano or C 1 -C alkoxy or is optionally monosubstituted to triple, identically or differently substituted by halogen or CpC ⁇ alkyl, C 3 -C 6 -cycloalkyl.
• R 3 preferably represents the groups —C— XR. - YR and _Q - p
• R 4 and R 5 are each independently preferably hydrogen, where appropriate, by halogen, cyano or C j -C 4 alkoxy
• C 1 -C 4 -alkyl or C 3 -C 6 -cycloalkyl which are optionally monosubstituted to trisubstituted, identically or differently, by halogen or C1-C 4 -alkyl.
• R 6 and R 7 independently of one another, preferably each represent phenyl, naphthyl, dihydronaphthyl and tetrahydronaphthyl which are optionally mono- to pentasubstituted or substituted differently, where the following may be mentioned as substituents: hydroxy, amino, cyano, nitro, halogen; in each case optionally substituted by hydroxy, cyano or pialogenes C 1 -C 4 alkyl, Ci -
• Bromine optionally substituted C 2 -C 6 cycloalkyl and optionally phenyl; further C 1 -C 4 alkyl, C r C 4 alkoxy and C r C 4 - haloalkyl and C 1 -C 4 haloalkoxy each having 1 to 5 identical or different halogen atoms from the series fluorine, chlorine and bromine; and for an optionally mono- to pentasubstituted, identically or differently substituted, saturated or partially unsaturated or unsaturated mono- or tricyclic nitrogen-free heterocycle having 4 to 10 carbon atoms and 1 to 3 identical or different heteroatoms, such as O and S atoms, the substituents being those at
• X preferably represents C 1 -C 4 -alkyl or each mono- to pentasubstituted, identically or differently substituted, phenyl and naphthyl, the phenyl substituents mentioned for R 6 being suitable as substituents.
• X preferably represents a single bond, each straight-chain or branched Cj-Cg-alkanediyl, C 2 -C6 -alkenediyl or C 2 -C, 5-alkynediyl and for the groups -AO-, -AS-, -AO-A ' -, -AS-A'-, -AN (Alk) - or -AN (Alk) -A'-, where
• Alk preferably represents C 1 -C 4 -alkyl
• a and A 'independently of one another are preferably straight-chain or branched Cj-C 6 -alkanediyl.
• Y preferably represents a single bond
• R particularly preferably represents cyano or nitro.
• R 1 particularly preferably represents hydrogen, in each case optionally by
• Phenyl where the phenyl substituents mentioned for R 6 are suitable as substituents.
• R 2 particularly preferably represents hydrogen, in each case methyl, ethyl, n- or i-propyl and n-, i-, s- or t-butyl optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy, or in each case optionally Single to triple, the same or different, fluorine, chlorine, bromine, methyl or ethyl substituted cyclopropyl, cyclopentyl and cyclohexyl.
• R 3 particularly preferably represents the groupings and _ 0 - R 8 , in which
• R 4 and R 5 independently of one another are particularly preferably hydrogen, for methyl, ethyl, n- or i-propyl and n-, i-, s- or t-butyl which are each optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy, or for cyclopropyl, cyclopentyl and cyclohexyl which are optionally monosubstituted to trisubstituted, identically or differently, by fluorine, chlorine, bromine, methyl or ethyl.
• R 6 and R 7 independently of one another are particularly preferably each phenyl, naphthyl, dihydronaphthyl and tetrahydronaphthyl which may be monosubstituted to trisubstituted by identical or different substituents, the following being mentioned as substituents: cyano, nitro, amino, fluorine, chlorine, bromine; each optionally substituted by fluorine or chlorine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methylamino, ethylamino, n- or i-propylamino or dimethylamino; in each case optionally substituted by fluorine and / or chlorine, acetyl, propionyl, methoxycarbonyl,
• Cyano nitro, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, methoxy, ethoxy, trifluoromethyl, trifluoromethoxy, trifluoromethylthio and dimethylamino.
• R 8 is particularly preferably methyl, ethyl, n- or i-propyl; n-, i-, s- or t-butyl or phenyl which is optionally monosubstituted to trisubstituted identically or differently, the phenyl substituents mentioned for R 6 being suitable as substituents.
• X particularly preferably stands for a single bond and for
• Y particularly preferably stands for a single bond and for
• R very particularly preferably represents cyano or nitro.
• R 1 very particularly preferably represents hydrogen, methyl, ethyl, n- or i-propyl, cyclopropyl or phenyl.
• R 2 very particularly preferably represents hydrogen, methyl, ethyl, n- or i-propyl or cyclopropyl.
• R 3 very particularly preferably represents the groupings
• R 4 and R 5 independently of one another very particularly preferably represent hydrogen, methyl, ethyl, n- or i-propyl and cyclopropyl.
• R 6 and R 7 independently of one another very particularly preferably represent phenyl or naphthyl which may be monosubstituted to trisubstituted identically or differently, the following being mentioned as substituents:
• Cyano nitro, amino, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, trifluoromethyl, difluoromethyl , Trifluoromethoxy, difluoromethoxy, trifluoromethylthio, methylamino, dimethylamino, acetyl, propionyl, methoxycarbonyl, ethoxycarbonyl, methylthio, methylsulfinyl,
• Methylsulfonyl methylaminocarbonyl, ethylaminocarbonyl, n- or i-propylaminocarbonyl, dimethylaminocarbonyl and diethylaminocarbonyl; and in each case optionally by cyano, nitro, fluorine, chlorine, methyl, methoxy, methylthio, methylsulfinyl, methylsulfonyl, trifluoromethyl or trifluoromethoxy, trifluoromethylthio,
• substituents may be mentioned: cyano, nitro, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, methoxy, trifluoromethyl or dimethylamino or optionally substituted phenyl, the substituents being suitable for the phenyl radical come, which are also mentioned under R 6 for the phenyl radical.
• R 8 very particularly preferably for methyl, ethyl, n- or i-propyl; n-, i-, s- or t-butyl or phenyl which is optionally monosubstituted to trisubstituted identically or differently, the phenyl substituents mentioned for R 6 being suitable as substituents.
• X very particularly preferably stands for a single bond and for
• Preferred compounds according to the invention are substances of the formulas (I a) to (I h):
• R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , X and Y stand for the abovementioned general, preferred, particularly preferred and very particularly preferred meanings.
• Preferred compounds according to the invention are also substances of the formulas (I A) to
• NC - N C-NH-R 3
• R 3 , R 4 , R 5 and R 6 represent the abovementioned general, preferred, particularly preferred and very particularly preferred meanings.
• Preferred compounds according to the invention are also substances of the formulas (I-I) to (1-56)
• NC - N C ⁇ NI - CH ⁇ 2 -R ° i 1 - ,. (1-3)
• NC - N C - N - CH (CH,) - CH ⁇ -R 6
• NC - N C - N - CH (CH 3 ) - CH 2 CH - R 6
• NC - N C - N - OCH (CH 3 ) CH 2 CH - R 7 1 1 o (1-14)
• NC - N C - N - CHj. - (CH 2,) 'Z -R b (1-15)
• NC - N C - N - CH (CH 3 ) - (CH 2 ) - R 6
• NC— N C— N-OCH (CH 3 ) CH 2 O— R 7 1 (1-20)
• NC - N CI - NI - CH 2 - CH, 2S - R D
• NC - N C - NO (CH 2 ) 2 SO-R 7
• NC - N C - NO (CH 2 ) 2 SO 2 -R 7
• NC - N C - N - CH (CH 3 ) - CH 2 OCH - R 6
• NC - N C - N - CH (CH - CH, SCH - R 6
• NC— N C— N-CH (CH,) - CH, SOCH R 6 1 '9 (1-38)
• NC - N C - N - CH (CH 3 ) - CH 2 CH 2 S - R 6
• NC— N C— N-CH -CH 2 N (CH 3 ) - R b (1-49)
• NC - N C - N - CHr - N (C, H - R 6
• NC - N C - N - CH 2 - CH 2 CH 2 N (CH 3 ) -R 6
• NC - N C - N - CH - CH 2 N (C 2 H 5 ) CH R 6
• NC— N C— N-CH— CH 2 CH 2 N (CH 3 ) CH R 6 1 I 9 (1-55)
• R 1 , R 2 , R 6 and R 7 stand for the abovementioned general, preferred, particularly preferred and very particularly preferred meanings.
• hydrocarbon radicals such as alkyl or alkenyl - also in connection with heteroatoms, such as alkoxy or alkyl thio - are in each case straight-chain or branched as far as possible.
• R 1 , R 2 and XR 6 as listed in Table 1.
• R 1 , R 2 and XR 6 as listed in Table 1.
• R 1 , R 2 and XR 6 as listed in Table 1.
• R 1 , R 2 and XR 6 as listed in Table 1.
• R i C 3 H 7 -i
• R 2 C 2 H 5
• R 2 C 2H 5
• R 2 C 3 H 7 -i
• R 2 C 2 H 5
• R 2 C 2 H 5
• R l C 3 H 7 -n
• R 2 C 2 H 5
• R 2 C 2 H 5
• R i C 2 H 5
• R 2 H YR 7 as listed in Table 1 15. 00/03976 - 34 -
• Table 120 Compounds in Table 120 correspond to the general formula (I c), in which
• YR 7 as listed in Table 1 15 on A. 00/03976 _ 35 _
• Table 125 Compounds in Table 125 correspond to the general formula (I c), in which
• R 2 C 2 H 5
• R 2 C 3 H 7 -i
• Table 130 Compounds in Table 130 correspond to the general formula (I c), in which
• R 2 C 2 H 5
• R6 vvie listed in table b, as well as additional
• R 6 as listed in Table e.
• NC— N CN— Y - R 7 L.1 'n (I c)
• Formula (II) provides a general definition of the ethanimide esters required as starting materials for carrying out the process according to the invention.
• Z is preferably C 4 -C 4 -alkyl, in particular methyl or ethyl.
• N-cyanoethanimidic acid esters are largely known (see, for example, US 5,304,566 or J. Org. Chem. 28, 1963, 1816-1821) and / or can be obtained by customary processes.
• N-nitro-ethanimidic acid esters are obtained, for example, by nitrating the corresponding NO 2 -free ethanimidic acid esters of the formula (II) in a conventional manner.
• the amines of the general formula (III) to be used as starting materials in the process according to the invention are generally known compounds of organic chemistry or can be obtained in a generally known manner.
• the process according to the invention is preferably carried out in the presence of a diluent.
• Alcohols such as methanol and ethanol can preferably be used; Nitriles such as acetonitrile or esters such as ethyl acetate. It is also possible to work in water or organic-aqueous mixtures if necessary.
• reaction temperatures can be carried out when carrying out the process according to the invention.
• Process can be varied over a wide range. In general, temperatures between 0 ° C and 100 ° C, preferably between 20 ° C and 80 ° C.
• the end products are worked up and isolated in a generally known manner.
• the active substances are suitable for combating animal pests, in particular insects, arachnids and nematodes, which occur in agriculture, in forests, in the protection of stored goods and materials, and in the hygiene sector. They can preferably be used as pesticides. They are effective against normally sensitive and resistant species as well as against all or individual stages of development.
• the pests mentioned above include:
• Isopoda e.g. Oniscus asellus, Armadillidium vulgare, Porcellio scaber. From the order of the Diplopoda e.g. Blaniulus guttulatus.
• Chilopoda for example, Geophilus carpophagus and Scutigera spp.
• Symphyla for example, Scutigerella immaculata.
• Thysanura e.g. Lepisma saccharina.
• Orthoptera e.g. Acheta domesticus, Gryllotalpa spp., Locusta migratoria migratorioides, Melanoplus spp., Schistocerca gregaria.
• Phthiraptera e.g. Pediculus humanus corporis, Haematopinus spp., Linognathus spp., Trichodectes spp., Damalinia spp ..
• Thysanoptera e.g. Hercinothrips femoralis, Thrips tabaci
• Aleurodes brassicae Bemisia tabaci
• Trialeurodes vaporariorum Aphis gossypii, Brevicoryne brassicae, Cryptomyzus ribis, Aphis fabae, Aphis pomi, Eriosoma lanigerum, Hyalopterus arundinis, Phylloxera vastatrix, Pemphigususpp.
• Leptinotarsa decemlineata Phaedon cochleariae, Diabrotica spp., Psylliodes chrysocephala, Epilachna varivestis, Atomaria spp., Oryzaephilus surinamensis, Anthonomus spp., Sitophilus spp., Otiorrhynchus sulcatordimidhmpphppm, spp.
• Anthrenus spp. Attagenus spp., Lyctus spp., Meligethes aeneus, Ptinus spp., Niptus hololeucus, Gibbium psylloides, Tribolium spp., Tenebrio molitor, Agriotes spp., Conoderus spp., Melolontha melolontha., Amphimalltra solitus
• Hymenoptera e.g. Diprion spp., Hoplocampa spp., Lasius spp.
• Drosophila melanogaster Musca spp., Fannia spp., Calliphora erythrocephala, Lucilia spp., Chrysomyia spp., Cuterebra spp., Gastrophilus spp., Flyppobosca spp., Stomoxys 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., Liriomy
• Acarina e.g. Acarus siro, Argas spp., Ornithodoros spp., Dermanyssus gallinae, Eriophyes ribis, Phyllocoptruta oleivora, Boophilus spp.,
• Rhipicephalus spp. Amblyomma spp., Hyalomma spp., Ixodes spp., Psoroptes spp., Chorioptes spp., Sarcoptes spp., Tarsonemus spp., Bryobia praetiosa, Panonychus spp., Tetranychus 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., Bursa.
• the compounds of the formula (I) according to the invention are notable in particular for good nematicidal activity. For example, they can be used with particularly good success to combat Meloidogyne incognita
• 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, active ingredient-impregnated natural and synthetic substances and very fine encapsulations in polymers Fabrics.
• the compounds according to the invention show herbicidal effects in some cases.
• These 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, that is to say emulsifiers and / or dispersants and / or foam-producing 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 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.
• Talc chalk, quartz, attapulgite, montmorillonite or diatomaceous earth ' and synthetic rock flour, such as highly disperse silica, aluminum oxide and silicates, are suitable as solid carriers for granules: e.g.
• suitable emulsifiers and / or foam-generating agents are: for example nonionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example alkylaryl polyglycol ethers, alkyl sulfonates, Alkyl sulfates, aryl sulfonates and protein hydrolyzates;
• Possible dispersing agents are, for example, lignin sulfite waste liquor and methyl cellulose.
• Adhesives such as carboxymethyl cellulose, natural and synthetic powdery, granular or latex-shaped polymers, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, and natural phospholipids such as cephalins and lecithins and synthetic phospholipids can be used in the formulations.
• Other additives can be mineral and vegetable oils.
• Dyes such as inorganic pigments, e.g. Iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin, azo and metal phthalocyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc can be used.
• the formulations generally contain between 0.1 and 95% by weight of active compound, preferably between 0.5 and 90%.
• the active compound according to the invention can be mixed with other active compounds, such as insecticides, attractants, sterilants, bactericides,
• Insecticides include, for example, phosphoric acid esters, carbamates, carboxylic acid esters, chlorinated hydrocarbons, phenylureas, substances produced by microorganisms, etc.
• Fungicides are particularly favorable mixed partners:
• Famoxadon Fenapanil, Fenarimol, Fenbuconazol, Fenfuram, Fenitropan, Fenpiclonil, Fenpropidin, Fenpropimo ⁇ h, Fentinacetat, Fentinhydroxyd, Ferbam, Ferimzon, Fluazinam, Flumetover, Fluoromid, Fluquinconazol, Flu ⁇ rimidol, Flutilanol, Flusil- fililol, Flusilanol, Flusil- fililol, Flusil- fililol, Flusil- fililol-, Flusil- fidol, Flusil- fidol, Flusil- fidil, Flusil- fidol, Flusil- fidol, Flusil- fidol, Flusil- fidol, Flusil- fidol, Flusil- fidol, Flusil- fidol, Flusil- fidol, Flus
• 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,
• Metconazole methasulfocarb, methfuroxam, metiram, metomeclam, metsulfovax, mildiomycin, myclobutanil, myclozolin,
• Oxadixyl Oxamocarb, Oxolinicacid, Oxycarboxim, Oxyfenthiin,
• Paclobutrazole pefurazoate, penconazole, pencycuron, phosdiphen, pimaricin, piperalin.
• Tebuconazole Tebuconazole, tecloftalam, tecnazene, Tetcyclacis, tetraconazole, thiabendazole, Thicyofen, Thifluzamide, thiophanate-methyl, thiram, Tioxymid, tolclofos-methyl, tolylfluanid, triadimefon, triadimenol, Triazbutil, triazoxide, Trichlamid, tricyclazole, Tridemo ⁇ h, triflumizole, triforine, triticonazole, O 00/03976
• Bacillus thuringiensis Bendiocarb, Benfuracarb, Bensultap, Betacyfluthrin, Bifenthrin, BPMC, Brofenprox, Bromophos A, Bufencarb, Buprofezin, Butocarboxim, Butylpyridaben,
• Fenamiphos Fenazaquin, Fenbutatinoxid, Fenitrothion, Fenobucarb, Fenothiocarb, Fenoxycarb, Fenpropathrin, Fenpyrad, Fenpyroximat, Fenthion, Fenvalerate,
• Fipronil fluazinam, flucycloxuron, flucythrinate, flufenoxuron, flufenprox, fluvalinate, fonophos, formothion, fosthiazate, fubfenprox, furathiocarb,
• HCH heptenophos, hexaflumuron, hexythiazox, Imidacloprid, Iprobefos, Isazophos, Isofenphos, Isoprocarb, Isoxathion, Ivermectin,
• Methamidophos Methidathion, Methiocarb, Methomyl, Metolcarb, Mübemectin, Monocrotophos, Moxidectin,
• Parathion A Parathion M, Permethrin, Phenthoat, Phorat, Phosalon, Phosmet, Phosphamidon, Phoxim, Pirimicarb, Pirimiphos M, Pirimiphos A, Profenofos, Promecarb, Propaphos, Propoxur, Prothiofos, Prothoat, Pymetrozin, Pyrachlophos,
• Tebufenozid Tebufenpyrad
• Tebupirimiphos Teflubenzuron
• Tefluthrin Temephos
• .Terbam Terbufos
• Tetrachlorvinphos Thiafenox, Thiodicarb, Thiofanox, Thio-methon, Thionazin, Thuringiensin, Tralomenhriazonium, Tralomenhriazon, Tronomenhrononium, Tronomenhrononium, Tronomenhriazon
• the active compounds according to the invention can also be used in their commercially available formulations and in the formulations thereof
• 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 ingredient concentration of the use forms can be from 0.0000001 to 95% by weight of active ingredient, 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.
• the compounds according to the invention also show herbicidal properties or plant growth-regulating activity, such as a defoliant effect.
• 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, mite mites, running mites, flies (stinging and licking), parasitic fly larvae and lice. Hair lice, featherlings and fleas.
• animal parasites ectoparasites
• ectoparasites such as tick ticks, leather ticks, mite mites, running mites, flies (stinging and licking), parasitic fly larvae and lice. Hair lice, featherlings and fleas.
• parasites include: From the order of the Anoplurida, for example 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 .. From the order Diptera and the subordinates Nematocerina and Brachycerina e.g.
• Hybomitra spp. Atylotus spp., Tabanus spp., Haematopota spp., Philipomyia spp., Braula spp., Musca spp., Hydrotaea spp., Stomoxys spp., Haematobia spp., Morellia spp., Fannia spp., Glossina spp ., Calliphora spp., Lucilia spp., Chrysomyia spp., Wohlfahrtia spp., Sarcophaga spp., Oestrus spp., Hypoderma spp., Gasterophilus spp., Hippobosca spp., Lipoptena spp., Melophagus spp ..
• Siphonaptrida e.g. Pulex spp., Ctenocephalides spp., Xenopsylla spp., Ceratophyllus spp ..
• Actinedida Prostigmata
• Acaridida Acaridida
• Acarapis spp. Cheyletiella spp., Ornitrocheyletia spp., Myobia spp., Psorergates spp., Demodex spp., Trombicula spp., Listrophorus spp., Acarus spp.
• Tyrophagus spp. Caloglyphus spp., Hypodectes spp., Pterolichus spp., 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,
• Infest hamsters, guinea pigs, rats and mice By combating these arthropods, deaths and reduced performance (in the case of meat, milk, wool, skins, eggs, honey, etc.) are to be reduced, so that the use of the active compounds according to the invention enables more economical and simple animal husbandry.
• the active compounds according to the invention are used in the veterinary sector in a known manner by enteral administration in the form of, for example, tablets,
• the active compounds of the formula (I) can be used as formulations (for example powders, emulsions, flowable agents) which contain the active compounds in an amount of 1 to 80% by weight, directly or apply after 100 to 10,000-fold dilution or use it as a chemical bath.
• insects may be mentioned by way of example and preferably, but without limitation:
• Kalotermes flavicollis such as Lepisma saccarina.
• non-living materials such as preferably plastics, adhesives, glues, papers and cartons, leather, wood and wood processing products and paints.
• the material to be protected against insect infestation is very particularly preferably wood and wood processing products.
• Agents or mixtures containing them can be protected is to be understood as examples: construction timber, wooden beams, railway sleepers, bridge parts, jetties, wooden vehicles, boxes, pallets, containers, telephone poles, wooden cladding, wooden windows and doors, plywood, chipboard, carpentry work or wooden products, which are generally used in house construction or in carpentry.
• 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, if appropriate, 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 solvents with an evaporation number above 35 and a flash point above 30 ° C., preferably above 45 ° C.
• Corresponding mineral oils or their aromatic fractions or mineral oil-containing solvent mixtures, preferably white spirit, petroleum and / or alkylbenzene, are used as such low-volatility, water-insoluble, oily and oily solvents.
• Mineral oils with a boiling range of 170 to 220 ° C, white spirit with a boiling range of 170 to 220 ° C, spindle oil with a boiling range of 250 to 350 ° C, petroleum or aromatics with a boiling range of 160 to 280 ° C, Te ⁇ entinöl and Like. Used.
• liquid aliphatic hydrocarbons with a boiling range from 180 to 210 ° C. or high-boiling mixtures of aromatic and aliphatic hydrocarbons with a boiling range from 180 to 220 ° C. and / or locker oil and / or monochlomaphthalene, preferably ⁇ -monochloronaphthalene, are used. O 00/03976
• organic low-volatility oily or oily solvents with an evaporation number above 35 and a flash point above 30 ° C, preferably above 45 ° C can be partially replaced by slightly or medium-volatile organic chemical solvents, with the proviso that the solvent mixture also has an evaporation number 35 and a flash point above 30 ° C, preferably above 45 ° C, and that the insecticide-fungicide mixture is soluble or emulsifiable in this solvent mixture.
• part of the organic chemical solvent or solvent mixture or an aliphatic polar organic chemical solvent or solvent mixture is replaced.
• 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 organic-chemical binders are the water-thinnable and / or synthetic resins which are soluble or dispersible or emulsifiable in the organic-chemical solvents used and / or binding drying oils, in particular binders consisting of or containing an acrylate resin, a vinyl resin, e.g. Polyvinyl acetate, polyester resin, polycondensation or polyaddition resin, polyurethane resin, alkyd resin or modified alkyd resin, phenolic resin, hydrocarbon resin such as indene-coumarone resin, silicone resin, drying vegetable and / or drying oils and / or physically drying binders based on a natural and / / or synthetic resin.
• binders consisting of or containing an acrylate resin, a vinyl resin, e.g. Polyvinyl acetate, polyester resin, polycondensation or polyaddition resin, polyurethane resin, alkyd resin or modified alkyd resin, phenolic resin, hydrocarbon resin such as in
• 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, in itself Known dyes, pigments, water-repellent agents, odor correctors and inhibitors or anticorrosive agents and the like can be used.
• Alkyd resins with an oil content of more than 45% by weight, preferably 50 to 68% by weight, are preferably used according to the invention.
• binder mentioned can be replaced by a fixative (mixture) or a Weichrnacher (mixture). These additives are intended to volatilize the active ingredients and crystallize or precipitate! prevent. They preferably replace 0.01 to 30% of the binder (based on 100% of the binder used).
• the plasticizers come from the chemical classes of phthalic acid esters such as dibutyl, dioctyl or benzyl butyl phthalate, phosphoric acid esters such as tributyl phosphate, adipic acid esters such as di- (2-ethylhexyl) adipate, stearates such as butyl stearate or amyl stearate, oleates such as butyl oleate, higher glycerol glycerol or glycerol ether - Kolether, glycerol ester and p-toluenesulfonic acid ester.
• phthalic acid esters such as dibutyl, dioctyl or benzyl butyl phthalate
• phosphoric acid esters such as tributyl phosphate
• adipic acid esters such as di- (2-ethylhexyl) adipate
• 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 by industrial impregnation processes, e.g. vacuum, double vacuum or pressure processes.
• the ready-to-use compositions can optionally contain further insecticides and, if appropriate, one or more fungicides.
• the insecticides and fungicides mentioned in Wo 94/29 268 are particularly suitable as additional mixing partners.
• the compounds mentioned in this document are an integral part of the present application.
• Very particularly preferred mixing partners can be insecticides, such as chlorpyriphos, phoxime, silafluofin, alphamethrin, cyfluthrin, cypermethrin, deltamethrin,
• Permethrin Permethrin, imidacloprid, NI-25, flufenoxuron, hexaflumuron and triflumuron, and fungicides such as epoxyconazole, hexaconazole, azaconazole, propiconazole, tebuconazole, cyproconazole, metconazole, imazalil, dichlofluanid, tolylfluanid, 3-iodo-2-propynyl-butylcarbamate, N-octyl -isothiazolin-3-one and 4,5-dichloro-N-octylisothiazolin-3-one.
• fungicides such as epoxyconazole, hexaconazole, azaconazole, propiconazole, tebuconazole, cyproconazole, metconazole, imazalil, dichlofluanid, tolylfluanid, 3-io
• Test nematode Meloidogyne incognita
• 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 mixed intimately with the soil that is contaminated with the test nematodes.
• the treated soil is poured into pots, seeds are sown and the pots are kept at a greenhouse temperature of 25 ° C.
• the lettuce roots are examined for nematode infestation (root galls) and the efficiency of the active ingredient is determined in%.
• the efficiency is 100% if the infestation is completely avoided, it is 0% if the infestation is as high as that of the control plants in untreated, but equally contaminated soil.

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• Chemical & Material Sciences (AREA)
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• Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
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• 1999
  • 1999-07-07 JP JP2000560085A patent/JP2002520385A/ja active Pending
  • 1999-07-07 AU AU51573/99A patent/AU5157399A/en not_active Abandoned
  • 1999-07-07 BR BR9912242-1A patent/BR9912242A/pt not_active IP Right Cessation
  • 1999-07-07 CN CN99810187A patent/CN1314881A/zh active Pending
  • 1999-07-07 CA CA002337773A patent/CA2337773A1/en not_active Abandoned
  • 1999-07-07 AT AT99936489T patent/ATE266631T1/de not_active IP Right Cessation
  • 1999-07-07 WO PCT/EP1999/004747 patent/WO2000003976A1/de not_active Ceased
  • 1999-07-07 US US09/743,588 patent/US6638979B1/en not_active Expired - Fee Related
  • 1999-07-07 ES ES99936489T patent/ES2221407T3/es not_active Expired - Lifetime
  • 1999-07-07 EP EP99936489A patent/EP1097128B1/de not_active Expired - Lifetime
  • 1999-07-15 AR ARP990103483A patent/AR029738A1/es not_active Application Discontinuation
  • 1999-07-15 EG EG86399A patent/EG22587A/xx active

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