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EP1858899A1 - Acrylamide heterobicyclique - Google Patents

Acrylamide heterobicyclique

Info

Publication number
EP1858899A1
EP1858899A1 EP06707280A EP06707280A EP1858899A1 EP 1858899 A1 EP1858899 A1 EP 1858899A1 EP 06707280 A EP06707280 A EP 06707280A EP 06707280 A EP06707280 A EP 06707280A EP 1858899 A1 EP1858899 A1 EP 1858899A1
Authority
EP
European Patent Office
Prior art keywords
propyl
alkyl
chloro
trifluoromethyl
methyl
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Withdrawn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
EP06707280A
Other languages
German (de)
English (en)
Inventor
Hans-Georg Schwarz
Jürgen Scherkenbeck
Graham Holmwood
Jürgen WIESCHEMEYER
Peter Lösel
Olga Malsam
Mark Wilhelm Drewes
Karl-Heinz Kuck
Ulrike Wachendorff-Neumann
Christian Arnold
Vincent Lee Salgado
Thomas Bretschneider
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 EP1858899A1 publication Critical patent/EP1858899A1/fr
Withdrawn legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
    • C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
    • C07D513/04—Ortho-condensed systems
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system

Definitions

  • the present invention relates to the use of known and novel heterobicyclic acrylamides and their derivatives as crop treatment agents, in particular for combating animal pests, plant treatment compositions based on known and novel heterobicyclic acrylamides and their derivatives, and novel heterobicyclic acrylamides and their derivatives and processes for their preparation ,
  • Heterobicyclic acrylamides have already been described for use as medicaments (in particular as antihypertensives, diuretics and uricosurica) (see EPO 189071 A2, EP0041215 A2, EP0088323 A2, EP0141072 A2, Sigrist et al., Developments in Nephrology 1987, 18 (diuretics), 547-549, Abdelal et al., Scientia Pharmaceutica, 1993, 61 (1), 21-33; Akahane et al., Bioorganic & Med. Chem. Lett., 1996, 6 (17), 2059-2062).
  • heterobicyclic acrylamides of the general formula (I) have a high activity against animal pests
  • a 1 is sulfur, oxygen, NH or N-alkyl
  • a 2 is nitrogen or carbon represented by hydrogen, halogen, hydroxy, in each case straight-chain, branched or halogenated alkyl, by optionally halogenated
  • R 1 is hydrogen, halogen, hydroxyl, cyano, nitro, optionally substituted by halogen, hydroxy, cyano, alkyl, haloalkyl, alkylamino, dialkylamino or alkoxy-substituted cycloalkyl, aryl, heteroaryl, optionally substituted by halogen, hydroxy, cyano,
  • R 3 is hydrogen, alkyl or trifluoromethyl
  • R 4 is hydrogen, cyano, trifluoromethyl, alkyl, halogen, alkoxy, nitro or SO "alkyl, wherein n is an integer from 0 to 2; represents straight-chain, branched or cyclic alkyl or represents the radical COR, where R is hydrogen, hydroxyl, alkyl, alkoxy, aralkoxy, aryloxy or NR'R "and R 'and R" have the meanings given for R 5 and R 6 ,
  • R 5 and R together or in each case stand for hydrogen, optionally substituted aryl, optionally substituted heteroaryl or a straight-chain, branched or cyclic, saturated or unsaturated aliphatic hydrocarbon radical which is optionally substituted by O, S, N-alkyl, NH, N-aryl or N-aralkyl is interrupted and is in each case optionally substituted by hydroxy, alkoxy, alkylmercapto, Alkylsulf ⁇ nyl, alkylsulfonyl, trialkylsilyl, alkyl, haloalkyl, halogen, optionally substituted phenyl, optionally substituted heteroaryl, alkoxycarbonyl, alkylamino or dialkylamino, the latter dialkyl radicals optionally together with the N atom a 5- to
  • R 5 and R 6 bridged together with the nitrogen atom, forms a 3- to 7-membered saturated or unsaturated ring which optionally contains 1 or 2 further heteroatoms from the group oxygen, sulfur or nitrogen, wherein the nitrogen is optionally substituted by hydrogen, alkyl, Aryl or aralkyl, and this 3- to 7-membered ring may be substituted by 1 to 4 identical or different substituents selected from the group alkyl, halogen, aryl, aralkyl, alkoxycarbonyl, hydroxyalkyl, alkoxyalkyl or trifluoromethyl or to 7-membered ring may be condensed with an optionally substituted aromatic ring.
  • a 1 is preferably sulfur, oxygen or NH,
  • a 1 particularly preferably represents sulfur or oxygen
  • a 1 very particularly preferably represents sulfur.
  • a 2 is preferably nitrogen or carbon which is hydrogen, halogen, hydroxy, optionally mono- or polyhalogenated alkyl, optionally mono- or polyhalogenated alkoxy or optionally mono- or polyhalogenated
  • a 2 particularly preferably represents nitrogen or carbon substituted by hydrogen, halogen, hydroxy, optionally mono- or poly-halogenated (Ci-C 6) alkyl, optionally mono- or poly-halogenated (Ci-C 6) alkoxy or optionally mono- or polyhalogenated (Ca-C 6 ) cycloalkyl is substituted.
  • a 2 very particularly preferably represents nitrogen or carbon which is substituted by hydrogen, chlorine, fluorine, bromine, hydroxyl, methyl, ethyl, isopropyl, cyclopropyl, methoxy, ethoxy, trifluoromethoxy, trifluoromethyl or 1-chloro-1-cyclopropyl is.
  • R 1 is preferably hydrogen, halogen, hydroxyl, cyano, nitro or optionally substituted by halogen, hydroxy, cyano, alkyl, haloalkyl, alkylamino, dialkylamino or alkoxy-substituted cycloalkyl, optionally substituted by halogen, hydroxy, cyano, alkylamino, dialkylamino or alkoxy substituted alkyl or optionally by
  • R 1 also preferably represents phenyl, which is optionally substituted one to five times by halogen, hydroxy, cyano, alkyl, alkoxy, haloalkyl, alkylamino or dialkylamino.
  • R 1 furthermore preferably represents heteroaryl, which is optionally mono- to disubstituted by halogen, hydroxyl, cyano, alkyl, alkoxy, haloalkyl, alkylamino or dialkylamino.
  • R 1 particularly preferably represents hydrogen, halogen, hydroxyl, cyano, nitro or in each case optionally by halogen, cyano, (C 1 -C 3 ) alkylamino and (C r
  • R 1 moreover preferably represents phenyl, which is optionally substituted one to five times by halogen, hydroxy, cyano, alkyl, alkoxy, (C 1 -C 3 ) haloalkyl, (C 1 -C 3 ) alkylamino or (C 1 -C 3 ) dialkylamino.
  • R 1 furthermore particularly preferably represents a five- or six-membered heteroaryl which is optionally mono- to disubstituted by halogen, hydroxyl, cyano, (C 1 -C 3 ) -alkyl, (Q-C 3 ) -alkoxy, (C r C 3 ) Haloalkyl, (Ci-C 3 ) alkylamino or (Ci-C 3 ) dialkylamino is substituted.
  • R 1 very particularly preferably represents hydrogen, fluorine, chlorine, bromine, hydroxyl or methoxy, ethoxy, isopropoxy, methylthio, methylsulfinyl, methylsulfonyl,
  • Trifluoromethoxy Trifluoromethoxy, trichloromethoxy, difluoromethoxy, difluorochloromethoxy,
  • R 1 also most preferably represents 4-chlorophenyl and 4- (trifluoromethyl) phenyl.
  • R 2 preferably represents phenyl which is optionally monosubstituted to pentasubstituted by halogen, cyano, (C] -C3) alkyl, (C 1 -C 3) -alkoxy, phenoxy, (C r C 3) haloalkyl, (C r C 3) alkylamino or (Ci-C is substituted by 3) dialkylamino, or for up to six membered heteroaryl, which is optionally monosubstituted to tetrasubstituted by halogen, cyano, (C r C 3) alkyl, (C r C 3) alkoxy, phenoxy, ( C r C 3 ) haloalkyl, (C r C 3 ) alkylamino or (C r C 3 ) dialkylamino.
  • R 2 particularly preferably represents 2-bromophenyl, 2-iodophenyl, 2-chlorophenyl, 3-chlorophenyl, 4-chlorophenyl, 2,4-dichlorophenyl, 2-fluorophenyl, 2,4-difluorophenyl, 2-chloro-4 2006/094666
  • R 2 very particularly preferably represents 2-bromophenyl, 2-iodophenyl, 2-chlorophenyl, 3-chlorophenyl, 4-chlorophenyl, 2,4-dichlorophenyl, 2-fluorophenyl, 2,4-difluorophenyl, 2-chloro-4 - fluo ⁇ henyl, 2-fluoro-4-chloro-phenyl, 2-methyl-phenyl, 2-ethyl-phenyl, 2-chloro-4-methyl-phenyl, 2-fluoro-4-methyl-phenyl, 2-methyl-4-chloro-phenyl, 4-fluoro-phenyl, 2-methyl 4-fluoro-phenyl, 3,4-dichloro-phenyl, 2,3-dichlorophenyl, 2,5-dichloro-phenyl, 2,3-difluorophenyl, 2,5-difluo-phenyl, 2,3,4-trifluoro-phenyl, 3,4
  • R 3 is preferably hydrogen, trifluoromethyl or (C, -C 6 ) alkyl.
  • R 3 is particularly preferably hydrogen.
  • R 4 preferably represents hydrogen, cyano, trifluoromethyl, (C, -C 6) alkyl, nitro, CO- (Ci - C 6) alkyl or SO 2 - (C 1 -C 6) AIlCyI.
  • R 4 particularly preferably represents hydrogen and cyano.
  • R 4 is very particularly preferably hydrogen.
  • R 5 and R 6 together or in each case preferably represent hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkyl-alkyl, alkoxyalkyl, di- (alkoxy) -alkyl, alkylthio-alkyl, Alkylsulfinyl-alkyl, alkylsulfonyl-alkyl, alkylamino-alkyl, dialkylaminoalkyl, trialkylsilyl-alkyl, haloalkyl, haloalkenyl, haloalkynyl, halocycloalkyl, haloalkylalkyl, haloalkoxyalkyl, each being mono- or polysubstituted by hydrogen, halogen, cyano, nitro , Alkyl and dialkylamino, haloalkyl, alkyl, haloalkoxy or alkoxy-substituted ary
  • R 5 and R 6 are also preferably, bridged together with the nitrogen atom, for a 3- to 7-membered saturated or unsaturated ring which optionally contains 1 or 2 further heteroatoms from the group oxygen, sulfur or nitrogen, wherein the nitrogen optionally by Is hydrogen, (Ci-C 6 ) alkyl, aryl or aralkyl substituted and wherein this 3- to 7-membered ring by 1 to 4 identical or different substituents from the group (C, -C 6 ) alkyl, (QC 6 ) haloalkyl , Halogen, aryl, aralkyl, (C r C 6 ) alkoxycarbonyl, (Q-C 6 ) alkoxyalkyl, or wherein this 3- to 7-membered ring may be condensed with an optionally substituted aromatic ring.
  • R 5 and R 6 are each alone or together particularly preferably represent hydrogen, (Q- C6) alkyl, (C 2 -C 6) AIkOTyI, (C 2 -C 6) alkynyl, (C 3 -C 6) cycloalkyl, (C 3 -C 6 ) cycloalkyl- (Q-C 4 ) alkyl, (QC 6 ) alkoxy- (QC 6 ) alkyl, di- ((C 1 -C 6 ) alkoxy) - (QC 6 ) alkyl, (QC 6 ) alkylthio (QC 6 ) alkyl, (QC 6 ) alkylsulfinyl (QC 6 ) alkyl, (QC 6 ) alkylsulfonyl (C r C 6 ) alkyl, (Q-
  • R 5 and R 6 are furthermore particularly preferably bridged together with the nitrogen atom, in each case optionally substituted by fluorine, chlorine, bromine, (QC 6 ) alkyl, trifluoromethyl and (QC 6 ) alkoxy-substituted piperidine, piperazine, morpholine or pyrrolidine.
  • R 5 and R 6 together or in each case very particularly preferably represent hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, AHyI, propargyl, cyclopropyl, Cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, 1- Pentyl, 2-pentyl, 3-pentyl, 2,2-dimethyl-1-propyl, 3-methyl-1-butyl, 3-dimethyl-1-butyl, 1,1-dimethyl-1-propyl, 1-methoxy 2-propyl, 2-methoxy-propyl, 1-ethoxy-2-propyl, 2-ethoxy-propyl, 2-methoxyethyl, 2-ethoxyethyl, 2- (methylthio) ethyl, 2- (ethylthio) ethyl, 2-
  • Chlorine -phenethyl, phenyl, 4-fluorophenyl, 4-chlorophenyl, 3-chlorophenyl, 2-chlorophenyl,
  • 2,4-dichlorophenyl 4-trifluoromethoxyphenyl, 4-trifluoromethyl-phenyl, (2-pyridyl) methyl, (2-pyridyl) -l-ethyl, (3-pyridyl) -methyl, (3-pyridyl) -l-ethyl, (4-pyridyl) -methyl,
  • R 5 and R 6 are also very particularly preferably bridged together with the nitrogen atom, for piperidine, piperazine, N-methylpiperazine, morpholine, 2,6-dimethylmorpholine, 2- (trifluoromethyl) piperidine, 3- (trifluoromethyl ) -piperidine, 4- (trifluoromethyl) -piperidine or pyrrolidine.
  • the compounds of the formula (I) may also, depending on the nature of the substituents, as stereoisomers, ie as geometric and / or optical isomers, or Isomer mixtures are present in different compositions. Both the pure stereoisomers and any mixtures of these isomers are the subject of this invention, although in general only the compounds of formula (I) is mentioned here.
  • the invention also provides the salt-like derivatives formed from compounds of the formula (I) by reaction with basic or acidic compounds.
  • the compounds of formula (I) 5 According to the invention particularly preferably contain a combination of the present meanings listed above as being particularly preferred.
  • hydrocarbon radicals such as alkyl - also in combination with heteroatoms, such as in alkoxy - as far as possible in each case straight-chain or branched.
  • a 2 is nitrogen or carbon which is substituted by hydrogen, chlorine, fluorine, bromine, hydroxyl, methyl, ethyl, isopropyl, cyclopropyl, methoxy, ethoxy, trifluoromethoxy, trifluoromethyl or 1-chloro-1-cyclopropyl,
  • R 1 represents hydrogen, fluorine, chlorine, bromine, hydroxyl or methoxy, ethoxy, isopropoxy, methylthio, methylsulfinyl, methylsulfonyl, trifluoromethoxy, trichloromethoxy,
  • R 2 is 2-chlorophenyl, 3-chlorophenyl, 4-chlorophenyl, 2,4-dichlorophenyl, 2-fluorophenyl, 2,4-difluo-biphenyl, 2-chloro-4-fluorophenyl, 2-fluoro-4-chlorophenyl, 2-methylphenyl , 2-ethylphenyl, 3-methylphenyl, 4-methylphenyl, 2-chloro-4-methylphenyl, 2-fluoro-4-methylphenyl, 2-methyl-4-chlorophenyl, 4-fluorophenyl, 2-methyl-4-fluoro-phenyl, 3 , 4-chlorophenyl, 3,5-dichlorophenyl, 2,3-dichlorophenyl, 2,5-dichlorophenyl, 3,4-difluorophenyl, 3,5-difluorophenyl, 2,3-difluorophenyl, 2,5-difluorophen
  • Methyl 4-methoxyphenyl, 4-phenoxyphenyl, 2-chloro-4-phenoxyphenyl, 2-fluoro-4-phenoxyphenyl, 2-methyl-4-phenoxy-phenyl, 4- (trifluoromethoxy) phenyl, 2- (trifluoromethyl) phenyl, 3- (trifluoromethyl) phenyl, 4- (trifluoromethyl) phenyl, 2-chloro-4- (trifluoromethyl) phenyl, 2-fluoro-4- (trifluoromethyl) phenyl, 4- (tert-butyl) phenyl, 4- Cyanophenyl, thienyl, 3-chlorothien-2-yl, 4-chlorothien-2-yl, 5-chlorothien-2-yl, 2-chlorothien-4-yl,
  • R 5 and R 6 together or in each case independently represent hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, allyl, propargyl, cyclopropyl, cyclobutyl, cyclopentyl , Cyclohexyl, cyclopropylmethyl, 1-pentyl, 2-pentyl, 3-pentyl, 2,2-dimethyl-1-propyl, 3-methyl-1-butyl, 3-dimethyl-1-butyl, 1,1-dimethyl-1 propyl, 1-methoxy-2-propyl, 2-
  • Chloro-5-pyridyl -l-ethyl, methoxy, ethoxy, iso-propoxy, cyclopropylmethoxy, benzyloxy, 1-phenethoxy or 2-phenethoxy,
  • R 5 and R 6 are bridged together with the nitrogen atom, for piperidine, piperazine, N-methylpiperazine, morpholine, 2,6-dimethyl-morpholine, 2- (trifluoromethyl) -piperidine, 3- (trifluoromethyl) -piperidine, 4- (Trifluoromethyl) piperidine or pyrrolidine.
  • R 2 very particularly preferably represents 2-bromophenyl, 2-iodophenyl, 2-chlorophenyl, 3-chlorophenyl, 4-chlorophenyl, 2,4-dichlorophenyl, 2-fluorophenyl, 2,4-difluorophenyl, 2-chloro-4 - fluo ⁇ henyl, 2-fluoro-4-chlorophenyl, 2-methylphenyl, 2-ethylphenyl, 2-chloro-4-methylphenyl, 2-fluoro-4-methylphenyl, 2-methyl-4-chlorophenyl, 4-fluorophenyl, 2-methyl 4-fluorophenyl, 3,4-dichlorophenyl, 2,3-dichlorophenyl, 2,5-dichlorophenyl, 2,3-difluorophenyl, 2,5-difluorophenyl, 2,3,4-trifluorophenyl, 3,4-bis (methoxy) phenyl
  • the substituted heterobicyclic acrylamides of the general formula (I) have interesting biological properties. They are distinguished in particular by their strong arthropodizide (insecticidal and acaricidal) as well as their nematicidal and fungicidal activity and can be used in agriculture, in forests, in the protection of stored products and in the hygiene sector.
  • the starting materials or intermediates of the general formulas (II) to (VIII) are either known and / or can be prepared by processes known per se (see Preparation Examples).
  • Starting materials of the general formula (II) are, for example, according to US4264616 A; Laduron et al., J. Fluorine Chem. 1995, 73 (1), 83-86; Suyama et al., Heterocycles, 2003, 60 (1), 121-129 or Abdel-Hafez et al., Arzneistoff-Forschung, 2002, 52 (11), 833-839.
  • the further synthesis steps of scheme (a) are described in principle in the cited references (EP0189071 A2, EP0041215 A2, EP0088323 A2, EP0141072 A2).
  • reaction temperatures can be varied within a substantial range when carrying out the process according to the invention. In general, one works at temperatures between 0 0 C and 150 0 C, preferably between 1O 0 C and 12O 0 C.
  • the erfmdungswashe process is generally carried out under atmospheric pressure. However, it is also possible to carry out the process according to the invention under elevated or reduced pressure-generally between 0.1 bar and 10 bar.
  • the starting materials are generally used in approximately equimolar amounts. However, it is also possible to use one of the components in a larger excess.
  • the reaction is generally carried out in a suitable diluent in the presence of a reaction auxiliary and the reaction mixture is generally stirred for several hours at the required temperature.
  • the workup is carried out by customary methods (see the preparation examples).
  • the compounds of the general formula (I) according to the invention can be converted into other compounds of the general formula (I) by methods known in principle. Some of these possible conversion reactions are outlined below by way of example:
  • salts with bases and salts ("adducts") with acids preferably salts with inorganic bases, such as alkali metal salts, for example sodium, potassium or cesium salts, alkaline earth metal salts, for example calcium or magnesium salts, ammonium salts, salts with organic bases, in particular with organic amines, for example triethylammonium, dicyclohexylammonium, N, N'-dibenzylethylenediammonium, pyridinium, picolinium or ethanolammonium salts, salts with inorganic acids, for example hydrochlorides, hydrobromides, dihydrosulfates, trihydrosulfates or phosphates, salts with organic carboxylic acids or organic sulfonic acids, for example formates, acetates, trifluoroacetates
  • Salts are formed according to standard salt preparation procedures.
  • the compounds of the invention are reacted with appropriate acids to form acid addition salts.
  • Representative acid addition salts are salts obtained, for example, by reaction with inorganic acids, such as, for example, sulfuric acid, hydrochloric acid, hydrobromic acid, phosphoric acid or organic carboxylic acids, such as acetic acid, trifluoroacetic acid, citric acid, succinic acid, lactic acid, formic acid, maleic acid, camphoric acid, phthalic acid, glycolic acid, Glutaric acid, stearic acid, salicylic acid, sorbic acid, cinnamic acid, picric acid, benzoic acid or organic sulfonic acids such as methanesulfonic acid and para-toluenesulfonic acid form.
  • inorganic acids such as, for example, sulfuric acid, hydrochloric acid, hydrobromic acid, phosphoric acid or organic carboxylic acids, such as acetic acid, triflu
  • the active compounds are suitable for good plant tolerance, favorable toxicity to warm-blooded animals and good environmental compatibility for the protection of plants and plant organs, for increasing crop yields, improving the quality of the crop and for controlling animal pests, in particular insects, arachnids and nematodes used in agriculture, in agriculture Forestry, gardens and recreational facilities, materials and supplies, and the hygiene sector. They can preferably be used as crop protection agents. They are effective against normally sensitive and resistant species as well as against all or individual stages of development.
  • the above mentioned pests include: From the order of Isopoda, for example, Oniscus asellus, Armadillidium vulgare, Porcellio scaber.
  • Symphyla e.g. 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. From the order of Thysanoptera e.g. Herculothrips femoralis, Thrips tabaci, Thrips palmi,
  • Nephotettix cincticeps Lecanium corni, Saissetia oleae, Laodelphax striatellus, Nilaparvata lugens,
  • Aonidiella aurantii, Aspidiotus hederae, Pseudococcus spp., Psylla spp. From the order of Lepidoptera e.g. Pectinophora gossypiella, Bupalus piniarius, Cheimatobia brumata, Lithocolletis blancardella, Hyponomeuta padella, Plutella xylostella, Malacosoma neustria, Euproctis chrysorrhoea, Lymantria spp., Bucculatrix thurberiella, Phyllocnistis citrella,
  • Agrotis spp. Agrotis spp., Euxoa spp., Feltia spp., Earias insulana, Heliothis spp., Mamestra brassicae, Panolis flammea, Spodoptera spp., Trichoplusia ni, Carpocapsa pomonella, Pieris spp., Chilo spp., Pyrausta nubilalis, Ephestia kuehniella, Galleria Mellonella, Tineola bisselliella, Tinea pellionella,
  • Hofinannophila pseudospretella Cacoecia podana, Capua reticulana, Choristoneura fumiferana,
  • Diptera e.g. Aedes spp., Anopheles spp., Culex spp., Drosophila melanogaster, Musca spp., Fannia spp., Calliphora erythrocephala, Lucilia spp., Chrysomyia spp., Cuterebra spp., Gastrophilus spp., Hyppobosca 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., Liriomyza spp .. From the Order of Siphonaptera eg Xenopsylla cheopis, Ceratophyllus spp. From the class of arachnids, e.g.
  • Scorpio maurus Latrodectus mactans, Acorus 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., Hemitarsonemus spp., Brevipalpus spp.
  • the plant parasitic nematodes include e.g. Pratylenchus spp., Radopholus similis, Ditylenchus dipsaci, Tylenchulus semipenetrans, Heterodera spp., Globodera spp., Meloidogyne spp., Aphelenchoides spp., Longidorus spp., Xiphitema spp., Trichodorus spp., Bursaphelenchus spp.
  • the compounds according to the invention can also be used in certain concentrations or application rates as herbicides or as safeners for this purpose, or as microbicides, for example as fungicides, antimycotics or bactericides. If appropriate, they can also be used as intermediates or precursors for the synthesis of further active ingredients.
  • plants and parts of plants can be treated.
  • plants are understood as meaning all plants and plant populations, such as desired and undesired wild plants or crop plants (including naturally occurring crop plants).
  • Crop plants can be plants which can be obtained by conventional breeding and optimization methods or by biotechnological and genetic engineering methods or combinations of these methods, including the transgenic plants and including the plant varieties which can or can not be protected by plant breeders' rights.
  • Plant parts are to be understood as meaning all aboveground and subterranean parts and organs of the plants, such as shoot, leaf, flower and root, examples of which include 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 propagating material such as cuttings, tubers, rhizomes, offshoots and seeds.
  • the treatment according to the invention of the plants and plant parts with the active ingredients is carried out directly or by acting on their environment, habitat or storage space according to the usual treatment methods, e.g. by dipping, spraying, evaporating, atomizing, spreading, spreading, injecting and propagating material, in particular in seeds, further by single or multilayer 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 superfine encapsulations in polymeric substances.
  • formulations are prepared in a known manner, e.g. by mixing the active compounds with extenders, ie liquid solvents and / or solid carriers, if appropriate using surface-active agents, ie emulsifiers and / or dispersants and / or foam-forming agents.
  • Suitable liquid solvents are essentially: aromatics, such as xylene, toluene, or alkylnaphthalenes, chlorinated aromatics and chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chloroethylenes 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.
  • 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.
  • Suitable solid carriers are: for example, ammonium salts and ground natural minerals, such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, and ground synthetic minerals, such as finely divided silica, alumina and silicates, as solid carriers for granules: eg broken and fractionated natural rocks such as calcite, marble, pumice, sepiolite, dolomite and synthetic granules of inorganic and organic flours and granules of organic material such as sawdust, coconut shells, corn cobs and tobacco stalks; suitable emulsifiers and / or foam formers are: for example nonionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol Ethers, for example alkylaryl polyglycol ethers, alkylsulfonates, alkyl sulfates, arylsulfonates and
  • Adhesives such as carboxymethylcellulose, natural and synthetic powdery, granular or latex-type polymers such as gum arabic, polyvinyl alcohol, polyvinyl acetate, and natural phospholipids such as cephalins and lecithins and synthetic phospholipids may be used in the formulations.
  • Other additives may 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.
  • 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.
  • the formulations generally contain between 0.1 and 95% by weight of active compound, preferably between 0.5 and 90%.
  • the substances according to the invention have a strong microbicidal activity and can be used for controlling unwanted microorganisms, such as fungi and bacteria, in crop protection and in the protection of materials.
  • Fungicides can be used to combat plant protection by Plasmodiophoromycetes, Oomycetes,
  • Chytridiomycetes Zygomycetes, Ascomycetes, Basidiomycetes and Deuteromycetes.
  • Bactericides can be used in crop protection for controlling Pseudomonadaceae, Rhizobiaceae, Enterobacteriaceae, Corynebacteriaceae and Streptomycetaceae.
  • Xanthomonas species such as Xanthomonas campestris pv. Oryzae;
  • Pseudomonas species such as Pseudomonas syringae pv. Lachrymans; Erwinia species, such as Erwinia amylovora;
  • Pythium species such as Pythium ultimum
  • Phytophthora species such as Phytophthora infestans
  • Pseudoperonospora species such as Pseudoperonospora humuli or
  • Plasmopara species such as Plasmopara viticola
  • Bremia species such as Bremia lactucae
  • Peronospora species such as Peronospora pisi or P. brassicae
  • Erysiphe species such as Erysiphe graminis
  • Sphaerotheca species such as Sphaerotheca fuliginea
  • Podosphaera species such as Podosphaera leucotricha
  • Venturia species such as Venturia inaequalis
  • Pyrenophora species such as, for example, Pyrenophora teres or P. graminea
  • Cilioli bolus species such as Cochliobolus sativus
  • Uromyces species such as Uromyces appendiculatus
  • Puccinia species such as Puccinia recondita
  • Sclerotinia species such as Sclerotinia sclerotiorum
  • Tilletia species such as Tilletia caries
  • Ustilago species such as Ustilago nuda or Ustilago avenae;
  • Pellicularia species such as, for example, Pellicularia sasakii; Pyricularia species, such as Pyricularia oryzae;
  • Fusarium species such as Fusarium culmorum
  • Botrytis species such as Botrytis cinerea
  • Septoria species such as Septoria nodorum
  • Leptosphaeria species such as Leptosphaeria nodorum
  • Cercospora species such as Cercospora canescens
  • Alternaria species such as Alternaria brassicae
  • Pseudocercosporella species such as Pseudocercosporella he ⁇ otrichoides.
  • the active compounds according to the invention also have a strong tonic effect in plants. They are therefore suitable for mobilizing plant-own defenses against attack by unwanted microorganisms.
  • plant-strengthening (resistance-inducing) substances are to be understood as meaning those substances which are capable of stimulating the defense system of plants in such a way that the treated plants undergo undesired subsequent inoculation
  • Microorganisms develop extensive resistance to these microorganisms.
  • Undesirable microorganisms in the present case are phytopathogenic fungi, bacteria and viruses.
  • the substances according to the invention can therefore be used to
  • the period of time within which protection is afforded generally extends from 1 to 10 days, preferably 1 to 7 days after the treatment of the plants with the active ingredients.
  • the good plant tolerance of the active ingredients in the necessary concentrations for controlling plant diseases allows treatment of above-ground parts of plants, of Planting and seed, and the soil.
  • the active compounds according to the invention are also suitable for increasing crop yield. They are also low toxicity and have good plant tolerance.
  • the substances according to the invention can be used to protect industrial materials against infestation and destruction by undesired microorganisms.
  • Technical materials as used herein mean non-living materials that have been prepared for use in the art.
  • engineering materials to be protected from microbial alteration or destruction by the active compounds of the present invention may be adhesives, glues, paper and board, textiles, leather, wood, paints and plastics, coolants, and other materials that may be infested or degraded by microorganisms .
  • materials to be protected are also parts of production plants, such as cooling water circuits, called, which can be affected by the proliferation of microorganisms.
  • technical materials which may be mentioned are preferably adhesives, glues, papers and cartons, leather, wood, paints, cooling lubricants and heat transfer fluids, particularly preferably wood.
  • microorganisms that can cause degradation or a change in the technical materials for example, bacteria, fungi, yeasts, algae and mucus organisms may be mentioned.
  • the active compounds according to the invention preferably act against fungi, in particular molds, wood-discolouring and wood-destroying fungi (Basidiomycetes) and against slime organisms and algae.
  • microorganisms of the following genera Altemaria such as Alternaria tenuis, Aspergillus such as Aspergillus niger, Chaetomium such as Chaetomium globosum, Coniophora such as Coniophora puetana, Lentinus such as Lentinus tigrinus, Penicillium such as Penicillium glaucum, Polyporus such as Polyporus versicolor , Aureobasidium, such as Aureobasidium pullulans, Sclerophoma, such as Sclerophoma pityophila, Trichoderma, such as Trichoderma viride, Escherichia, such as Escherichia coli,
  • the active compounds can be converted into the customary formulations, such as solutions, emulsions, suspensions, powders, foams, pastes, granules, aerosols, ultrapure encapsulations in polymeric substances and in seed shells, and ULV -KaIt- and warm mist formulations.
  • formulations are prepared in a known manner, for example by mixing the active compounds with extenders, ie liquid solvents, liquefied gases under pressure and / or solid carriers, optionally with the use of surface-active agents, ie emulsifiers and / or dispersants and / or foam-forming agents.
  • extenders ie liquid solvents, liquefied gases under pressure and / or solid carriers
  • surface-active agents ie emulsifiers and / or dispersants and / or foam-forming agents.
  • organic solvents can also be used as auxiliary solvents.
  • Suitable liquid solvents are essentially: aromatics such as xylene, toluene or alkylnaphthalenes, chlorinated aromatics or chlorinated aliphatic hydrocarbons such as chlorobenzenes, chloroethylenes or methylene chloride, aliphatic hydrocarbons such as cyclohexane or paraffins, eg petroleum fractions, alcohols such as butanol or glycol and their ethers and esters, ketones, such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents, such as dimethylformamide and dimethyl sulphoxide, and also water.
  • aromatics such as xylene, toluene or alkylnaphthalenes
  • chlorinated aromatics or chlorinated aliphatic hydrocarbons such as chlorobenzenes, chloroethylenes or methylene chloride
  • aliphatic hydrocarbons
  • liquefied gaseous diluents or carriers are meant those liquids which are gaseous at normal temperature and under normal pressure, for example aerosol propellants, such as halogenated hydrocarbons as well as butane, propane, nitrogen and carbon dioxide.
  • Suitable solid carriers are: for example ground natural minerals, such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, and ground synthetic minerals, such as finely divided silica, alumina and silicates.
  • solid carriers for granules are: for example, broken and fractionated natural rocks such as calcite, pumice, marble, sepiolite, dolomite and synthetic granules of inorganic and organic flours and granules of organic material such as sawdust, coconut shells, corn cobs and tobacco stalks.
  • Suitable emulsifiers and / or foam-formers are: for example nonionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example alkylaryl polyglycol ethers, alkylsulfonates, alkyl sulfates, arylsulfonates and protein hydrolysates.
  • Suitable dispersants are: for example lignin-sulphite liquors and methylcellulose.
  • Adhesives such as carboxymethyl cellulose, natural and synthetic powdery, granular or latex polymers may be used in the formulations, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, as well as natural phospholipids such as cephalins and lecithins, and synthetic phospholipids.
  • Other additives may be mineral and vegetable oils.
  • Dyes such as inorganic pigments such as 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 ingredient, preferably between 0.5 and 90%.
  • the active compounds according to the invention can be present in the commercial formulations as well as in the formulations prepared from these formulations in admixture with other active substances, such as insecticides, attractants, sterilants, bactericides, acaricides, nematicides, fungicides, growth-regulating substances or herbicides.
  • active substances such as insecticides, attractants, sterilants, bactericides, acaricides, nematicides, fungicides, growth-regulating substances or herbicides.
  • the insecticides include, for example, phosphoric acid esters, carbohydrates, carboxylic esters, chlorinated hydrocarbons, phenylureas, microorganism-produced substances, and the like.
  • Particularly favorable mixing partners are e.g. the following:
  • 2-phenylphenol 8-hydroxyquinoline sulfate; Acibenzolar-S-methyl; aldimorph; amidoflumet; Ampropylfos; Ampropylfos-potassium; andoprim; anilazine; azaconazole; azoxystrobin;
  • bilanafos binapacryl; biphenyl; bitertanol; Blasticidin-S; bromuconazole; Bupirimate;
  • Buthiobate butylamine; Calcium polysulfides; capsimycin; captafol; captan; carbendazim;
  • carboxin carpropamid; carvones; chinomethionat; Chlobenthiazone; Chlorfenazole; chloroneb; chlorothalonil; chlozolinate; Clozylacon; cyazofamid; cyflufenamid; cymoxanil; cyproconazole;
  • Fenbuconazole fenfuram; fenhexamid; Fenitropan; fenoxanil; fenpiclonil; fenpropidin;
  • fluoromides fluoxastrobin; fluquinconazole; flurprimidol; flusilazole; flusulfamide; flutolanil;
  • Imibenconazole Iminoctadine triacetate; Iminoctadine tris (albesilate); iodocarb; ipconazole;
  • iprobenfos iprodione; iprovalicarb; Irumamycin; isoprothiolane; Isovaledione; kasugamycin;
  • Metalaxyl-M metconazole; methasulfocarb; Methfuroxam; metiram; metominostrobin; Metsulfovax; mildiomycin; myclobutanil; myclozoline; natamycin; nicobifen; Nitro Thal-isopropyl;
  • prothioconazole pyraclostrobin; Pyrazohos; pyrifenox; pyrimethanil; pyroquilon; Pyroxyfur;
  • trifloxystrobin triflumizole; triforine; triticonazole; Uniconazole; Validamycin A; vinclozolin;
  • 1.1 carbamates for example alanycarb, aldicarb, aldoxycarb, allyxycarb, aminocarb, bendiocarb,
  • Acetylcholine receptor modulators are Acetylcholine receptor modulators
  • Camphechlor chlordane, endosulfan, gamma-HCH, HCH, heptachlor, lindane, methoxychlor
  • Fiproles for example acetoprole, ethiprole, fipronil, vaniliprole
  • Organotin compounds for example azocyclotin, cyhexatin, fenbutatin oxides
  • Electron transport inhibitors binding site 1 / site 1
  • METTs for example Fenazaquin, Fenpyroximate, Pyrimidifen, Pyridaben, Tebufenpyrad, Tolfenpyrad
  • Electron transport inhibitors (binding site 2 / site 2) 13.1 rotenone
  • Electron transport inhibitors (binding site 3 / site 3) 14.1 acequinocyl, fluacrypyrim
  • Octopaminergic agonists for example, amitraz 19.1 Inhibitors of magnesium-stimulated ATPase, for example propargite
  • 20.1 BDCAs for example N 2 - [l, l -dimethyl-2- (methylsulfonyl) ethyl] -3-iodo-Nl- [2-methyl-4- [1,2,2,2-tetrafluoro-1 - (trifluoromethyl ) ethyl] phenyl] -1,2-benzenedicarboxamide (CAS Reg.
  • Nereistoxin analogs for example thiocyclam hydroxalate, thiosultap sodium
  • the active compounds according to the invention can furthermore be present in the form of insecticides in their commercial formulations and in the formulations prepared from these formulations in admixture with synergists.
  • Synergists are compounds which increase the effect of the active ingredients without the added synergist itself having to be active.
  • the active compounds according to the invention can furthermore, when used as insecticides, be present in their commercial formulations and in the forms of use prepared from these formulations in mixtures with inhibitors which reduce degradation of the active ingredient after application in the environment of the plant, on the surface of plant parts or in plant tissues ,
  • the active substance content of the application forms prepared from the commercial formulations can vary within wide ranges.
  • the active ingredient concentration of the use forms may be from 0.0000001 to 95% by weight of active ingredient, preferably between 0.0001 and 1% by weight.
  • the application is done in a custom forms adapted to the application.
  • the active ingredient When used against hygiene and storage pests, the active ingredient is characterized by an excellent residual effect on wood and clay and by a good alkali stability on limed substrates.
  • plants and their parts can be treated.
  • wild-type or plant species obtained by conventional biological breeding methods such as crossing or protoplast fusion
  • plant cultivars and their parts are treated.
  • transgenic plants and plant cultivars obtained by genetic engineering if appropriate in combination with conventional methods (genetically modified organisms), and parts thereof are treated.
  • the term “parts” or “parts of plants” or “plant parts” has been explained above.
  • Plant varieties are understood as meaning plants having new traits which have been bred by conventional breeding, by mutagenesis or by recombinant DNA techniques. These can be varieties, biotypes and genotypes.
  • the treatment according to the invention may also give rise to superadditive (“synergistic”) effects.
  • the preferred plants or plant cultivars to be treated according to the invention include all plants which, as a result of the genetic engineering modification, obtained genetic material which gives these plants particularly advantageous valuable properties ("traits").
  • traits are better plant growth, increased tolerance to high or low temperatures, increased tolerance to dryness or to bottoms salt, increased flowering, easier harvesting, acceleration of ripeness, 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 emphasized examples of such properties are an increased defense of the plants against animal and microbial pests, as against insects, mites, phytopathogenic fungi, bacteria and / or viruses as well as an increased tolerance of the plants against certain herbicidal active substances.
  • transgenic plants include the important crops such as cereals (wheat, rice), corn, soybean, potato, cotton, tobacco, oilseed rape and fruit plants (with the fruits apples, pears, citrus fruits and grapes), with corn, soybean, potato , Cotton, tobacco and oilseed rape.
  • Traits which are particularly emphasized are the increased defense of the plants against insects, arachnids, nematodes and snails by toxins which are formed in the plants, in particular those which are produced by the genetic material from Bacülus thuringiensis (for example by the genes Cry ⁇ A (a) , Cry ⁇ A (b), Cry ⁇ A (c), CryllA, CrylllA, CryIIIB2, Cry9c Cry2Ab, Cry3Bb and CrylF and combinations thereof) in the plants (hereinafter "Bt plants”).
  • Traits also highlight the increased resistance of plants to fungi, bacteria and viruses by systemic acquired resistance (SAR), systemin, phytoalexins, elicitors and resistance genes and correspondingly expressed proteins and toxins. Traits which are furthermore particularly emphasized are the increased tolerance of the plants to certain herbicidally active compounds, for example imidazolinones, sulfonylureas, glyphosate or phosphinotricin (eg "PAT" gene). The genes which confer the desired properties (“traits”) can also occur in combinations with one another in the transgenic plants.
  • SAR systemic acquired resistance
  • PAT phosphinotricin
  • Bt plants are maize varieties, cotton varieties, soybean varieties and potato varieties, which are sold under the trade names YIELD GARD® (eg corn, cotton, soya), KnockOut® (eg Corn), StarLink® (eg corn), Bollgard® (cotton), Nucotn® (cotton) and NewLeaf® (potato).
  • YIELD GARD® eg corn, cotton, soya
  • KnockOut® eg Corn
  • StarLink® eg corn
  • Bollgard® cotton
  • Nucotn® cotton
  • NewLeaf® potato
  • herbicide-tolerant plants are maize varieties, cotton varieties and soybean varieties, which are sold under the trade names Roundup Ready® (tolerance to glyphosate eg corn, cotton, soy), Liberty Link® (tolerance to phosphinotricin, eg rapeseed), IMI® (tolerance against imidazolinone) and STS® (tolerance to sulfonylureas eg corn).
  • Herbicide-resistant (conventionally grown on herbicide tolerance) plants are also the varieties marketed under the name Clearfield® (eg corn) mentioned. Of course, these statements also apply to future or future marketed plant varieties with these or future developed genetic traits.
  • the plants listed can be treated particularly advantageously erf ⁇ ndungshack with the compounds of the general formula I or the active substance mixtures according to the invention.
  • the preferred ranges given above for the active compounds or mixtures also apply to the treatment of these plants.
  • the active compounds of the invention act not only against plant, hygiene and storage pests, but also in the veterinary sector against animal parasites (ectoparasites) such as ticks, leather ticks, mange mites, mites, flies (stinging and licking), parasitic fly larvae, lice, hair pieces, Featherlings and fleas.
  • animal parasites ectoparasites
  • ticks leather ticks, mange mites, mites, flies (stinging and licking), parasitic fly larvae, lice, hair pieces, Featherlings and fleas.
  • Anoplurida e.g. Haematopinus spp., Linognathus spp., Pediculns spp., Phtirus spp., Solenopotes spp.
  • heteropterid e.g. Cimex spp., Triatoma spp., Rhodnius spp., Panstrongylus spp.
  • Actinedida Prostigmata
  • Acaridida e.g. Acarapis spp., Cheyletiella spp., Ornitrocheyletia spp., Myobia spp., Psorergates spp., Demodex spp., Trombicula spp., Listrophorus spp., Acorus 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 farm animals, such as e.g. Cattle, sheep, goats, horses, pigs, donkeys, camels, buffaloes, rabbits, chickens, turkeys, ducks, geese, bees, other pets such as e.g. Dogs, cats, caged birds, aquarium fish and so-called experimental animals, such. Hamsters, guinea pigs, rats and mice.
  • arthropods are farm animals, such as e.g. Cattle, sheep, goats, horses, pigs, donkeys, camels, buffaloes, rabbits, chickens, turkeys, ducks, geese, bees, other pets such as e.g. Dogs, cats, caged birds, aquarium fish and so-called experimental animals, such. Hamsters, guinea pigs, rats and mice.
  • the use of the active compounds according to the invention is done in the veterinary sector in a known manner by enteral administration in the form of, for example, tablets, capsules, infusions, Drenchen, granules, pastes, BoIi, the feed-through process, suppositories, by parenteral administration, such as by Injections (intramuscular, subcutaneous, intravenous, intraperitoneal, etc.), implants, by nasal application, by dermal application in the form of, for example, dipping or bathing (dipping), spraying, pouring and spot-on, washing , the powdering and with the help of active ingredient-containing moldings, such as Collars, ear tags, tail tags, limb bands, holsters, markers, etc.
  • enteral administration in the form of, for example, tablets, capsules, infusions, Drenchen, granules, pastes, BoIi, the feed-through process, suppositories
  • parenteral administration such as by Injections (intramuscular
  • the active compounds of the formula (I) can be used as formulations (for example powders, emulsions, flowable agents) which contain the active ingredients in an amount of from 1 to 80% by weight, directly or apply after 100 to 10,000 times dilution or use as a chemical bath.
  • formulations for example powders, emulsions, flowable agents
  • the compounds according to the invention show a high insecticidal activity against insects which destroy industrial materials.
  • insects such as Hylotrupes bajulus, Chlorophosphus püosls, Anobium punctatum, Xestobium rufovillosum, Ptiliniis pecticornis, Dendrobium pertinex, Ernobius mollis, Priobivm carp ⁇ ni, Lyctus brunneus, Lyctus afi'icanus, Lyctus planicollis, Lyctus linearis, Lyctus pubescens, Trogoxylon aequale, Minthes rugicollis, Xyleborus spec. Tryptodendron spec. Apate monachus, Bostrychus capucins, Heterobostrychus brunneus, Sinoxylon spec. Dinoderus minutus;
  • Hymenoptera such as Sirexjuvencus, Urocerus gigas, Urocerus gigas taignus, Urocerus augur;
  • Termites such as Kalotermes flavicollis, Cryptotermes brevis, Heterotermes indicola, Reticulitermes flavipes, Reticulitermes santonensis, Reticulitermes lucifugus, Mastotermes darwiniensis, Zootermopsis nevadensis, Coptoterrnes formosanus;
  • Non-living materials such as preferably plastics, adhesives, glues, papers and cardboard, leather, wood, wood processing products and paints.
  • the material to be protected from insect attack is wood and woodworking products.
  • wood and woodworking products which can be protected by the composition according to the invention or mixtures containing it, is to be understood by way of example: Timber, wooden beams, railway sleepers, bridge parts, boat jetties, wooden vehicles, crates, pallets, containers, telephone poles, wooden cladding, wooden windows and doors, plywood, chipboard, carpentry or wood products, which are generally used in home construction or joinery.
  • the active compounds 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 compounds with at least one solvent or diluent, emulsifier, dispersing and / or binding or fixing agent, water repellent, optionally siccatives and UV stabilizers and optionally dyes and pigments, and further processing aids.
  • the insecticidal agents or concentrates used for the protection of wood and wood-based materials contain the active ingredient according to the invention in a concentration of 0.0001 to 95 wt .-%, in particular 0.001 to 60 wt .-%.
  • the amount of agents or concentrates used depends on the nature and occurrence of the insects and on the medium.
  • the optimal amount used can be determined in each case by test series. In general, however, it is sufficient to use 0.0001 to 20% by weight, preferably 0.001 to 10% by weight, of the active ingredient, based on the material to be protected.
  • the solvent and / or diluent used is an organic-chemical solvent or solvent mixture and / or an oily or oily high-volatile organic-chemical solvent or solvent mixture and / or a polar organic-chemical solvent or solvent mixture and / or water and optionally an emulsifier and / or wetting agent.
  • organic-chemical solvents are preferably oily or oily solvents having an evaporation number above 35 and a flash point above 30 0 C, preferably above 45 ° C used.
  • water-insoluble, oily and oily solvents corresponding mineral oils or their aromatic fractions or mineral oil-containing solvent mixtures, preferably white spirit, petroleum and / or alkylbenzene are used.
  • Mineral oils having a boiling range of 170 to 220 0 C, white spirit having a boiling range of 170 to 220 0 C., spindle oil with a boiling range of 250 to 35O 0 C, petroleum and aromatics with a boiling range of 160 to 28O 0 C, oil of turpentine and Like. For use.
  • the organic semi-volatile oily or oily solvents having an evaporation number above 35 and a flash point above 30 0 C, preferably above 45 ° C, can be partially replaced by light 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 0 C, preferably above 45 ° C, and that the insecticide-fungicide mixture in this solvent mixture is soluble or emulsifiable.
  • a portion 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 are used, for example glycol ethers, esters or the like.
  • the organic-chemical binders used are the water-dilutable and / or synthetic resins soluble in or soluble in or dispersible or emulsifiable synthetic resins and / or binding drying oils, in particular binders consisting of or containing Acrylate resin, a vinyl resin, eg Polyvinyl acetate, polyester resin, polycondensation or polyaddition resin, polyurethane resin, alkyd resin or modified alkyd resin, phenolic resin, hydrocarbon resin such as indene Cumaronharz, silicone resin, drying vegetable and / or drying oils and / or physically drying binder based on a natural and / or synthetic resin used.
  • binders consisting of or containing Acrylate resin, a vinyl resin, eg Polyvinyl acetate, polyester resin, polycondensation or polyaddition resin, polyurethane resin, alkyd resin or modified alkyd resin, phenolic resin, hydrocarbon resin such as indene Cumaronharz, silicone resin
  • the synthetic resin used as the binder may 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 repellents, odor correctors and inhibitors or corrosion inhibitors and the like can be used. According to the invention, at least one alkyd resin or modified alkyd resin and / or a drying vegetable oil is preferably present as the organic-chemical binder in the middle or in the concentrate. 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.
  • the mentioned binder can be completely or partially 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. Preferably, they replace 0.01 to 30% of the binder (based on 100% of the binder used).
  • the plasticizers are derived from the chemical classes of phthalic acid esters such as dibutyl, dioctyl or benzyl butyl phthalate, phosphoric 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 ethers or higher molecular weight glycol ethers, glycerol esters and p-toluenesulfonic acid ester.
  • phthalic acid esters such as dibutyl, dioctyl or benzyl butyl phthalate
  • phosphoric esters such as tributyl phosphate
  • adipic acid esters such as di (2-ethylhexyl) adipate
  • stearates such as butyl
  • Fixing agents are chemically based on polyvinyl alkyl ethers such as e.g. Polyvinyl methyl ether or ketones such as benzophenone, ethylene benzophenone.
  • Particularly suitable solvents or diluents are also water, optionally in admixture with one or more of the abovementioned organochemical solvents or diluents, emulsifiers and dispersants.
  • wood protection is provided by large scale impregnation methods, e.g. Vacuum, double vacuum or printing process achieved.
  • the ready-to-use agents may optionally contain further insecticides and optionally one or more fungicides.
  • Particularly preferred admixing partners may be insecticides such as chlorpyriphos, phoxim, silafluofin, alphamethrin, cyfluthrin, cypermethrin, deltamethrin, permethrin, imidacloprid, NI-25, flufenoxuron, hexaflumuron, transfluthrin, thiacloprid, methoxyfenozide, triflumuron, clothianidin, spinosad, tefluthrin, and fungicides such as epoxyconazole, hexaconazole, azaconazole, propiconazole, tebuconazole, cyproconazole, metconazole, imazalil, dichlorofluid, tolylfluanid, 3-iodo-2-propynyl-butylcarbamate, N-octyl-isothiazolin-3-one and 4,5-dichlor
  • the compounds according to the invention can be used to protect against fouling of objects, in particular hulls, sieves, nets, structures, quay systems and signal systems, which come into contact with seawater or brackish water.
  • Ectocarpus sp. and Ceramium sp. is particularly the fouling by sessile Entomostraken groups, which are summarized under the name Cirripedia (cirripeds), particular importance.
  • heavy metals such as e.g. in bis (trialkyltin) sulfides, trifluorobutyltin laurate, tri-n-butyltin chloride, copper (I) oxide, triethyltin chloride, tri-R-butyl (2-phenyl-4-chlorophenoxy) -tin, tributyltin oxide, molybdenum disulfide, Antimony oxide, polymeric
  • the ready-to-use antifouling paints may optionally contain other active substances, preferably algicides, fungicides, herbicides, molluscicides or other antifouling active ingredients.
  • AIs combination partners for the antifouling agents according to the invention are preferably: algicides such as 2-ter /'.- Burylamino-4-cyclopropylamino-6-methylthio-l, 3,5-triazine, dichlorophene, diuron, endothal, Fentinacetat, isoproturon, methabenzthiazuron , Oxyfluorfen, quinoclamines and terbutryn;
  • Fungicides such as BenzofZ ⁇ thiophenecarboxylic cyclohexylamide SjS dioxide, Dichlofluanid, Fluorfolpet, 3-iodo-2-propynyl-butylcarbamate, tolylfluanid and azoles such as Azaconazole, Cyproconazole, Epoxyconazole, Hexaconazole, Metconazole, Propiconazole and Tebuconazole;
  • Molluscicides such as fentin acetate, metaldehyde, methiocarb, niclosamide, thiodicarb and trimethacarb, Fe-chelates,
  • antifouling agents such as 4,5-dichloro-2-octyl-4-isothiazolin-3-one, diiodomethylparatrylsulfone, 2- (N, N-dimethylthiocarbamoylthio) -5-nitrothiazyl, potassium, copper, sodium and zinc salts of 2-pyridinethiol-1-oxide, pyridine-triphenylborane, tetrabutyldistannoxane, 2,3,5,6-tetrachloro-4- (methylsulfonyl) -pyridine, 2,4,5,6-tetrachloroisophthalonitrile, tetramethylthiuram disulfide and 2 , 4,6-Trichlor ⁇ henylmaleinimid.
  • the antifouling agents used contain the active ingredient of the compounds of the invention in a concentration of 0.001 to 50 wt .-%, in particular from 0.01 to 20 wt .-%.
  • the antifouling agents of the invention further contain the usual ingredients, 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, molluscicidal 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, especially 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, rosin esters or modified hard resins in combination with tar or bitumens, asphalt and epoxy compounds, small amounts of chlorinated rubber, chlorinated polypropylene and vinyl resins.
  • paints also contain inorganic pigments, organic pigments or dyes which are preferably insoluble in seawater.
  • paints may contain materials such as rosin to allow for controlled release of the active ingredients.
  • the paints may further contain plasticizers, rheology modifiers, and other conventional ingredients.
  • plasticizers such as rosin to allow for controlled release of the active ingredients.
  • rheology modifiers such as rheology modifiers, and other conventional ingredients.
  • self-polishing antifouling systems the compounds according to the invention or the abovementioned mixtures can also be incorporated.
  • the active substances are also suitable for controlling animal pests, in particular insects, arachnids and mites, which are used in enclosed spaces, such as apartments, for example.
  • Pests can be used alone or in combination with other active ingredients and adjuvants in household insecticide products. They are against sensitive and resistant species as well as against all
  • Acarina e.g. Argas persicus, Argas reflexus, Bryobia ssp., Dermanyssus gallinae, Gfyciphagus domesticus, Ornithodorus moubat, Rhipicephalus sanguineus, Trombicula alfreddugesi, Neutrombicula autwnn ⁇ lis, Dermatophagoides pteronissimus, Dermatophagoides forinae.
  • Acarina e.g. Argas persicus, Argas reflexus, Bryobia ssp., Dermanyssus gallinae, Gfyciphagus domesticus, Ornithodorus moubat, Rhipicephalus sanguineus, Trombicula alfreddugesi, Neutrombicula autwnn ⁇ lis, Dermatophagoides pteronissimus, Dermatophagoides forinae.
  • Opiliones phalangium Opiliones phalangium.
  • Zygentoma e.g. Ctenolepisma spp., Lepisma saccharina, Lepismodes mquilinus.
  • Diptera e.g. Aedes aegypti, Aedes albopictus, Aedes taeniorhynchus, Anopheles spp., Calliphora erythrocephala, Chrysozona pluvi ⁇ lis, Culex quinquefasciatus, Culex pipiens, Culex tarsalis, Drosophila spp., Fannia canicularis, Musca domestica, Phlebotomus spp., Sarcophaga carnaria, Simulium spp., Stomoxys Calcitrans, Tipula paludosa. From the order of Lepidoptera e.g.
  • Hymenoptera e.g. Camponotus herculeanus, Lasius fuliginosus, Lasius niger, Lasius umbratus, Monomer ium pharaonis, Paravespula spp., Tetramorium caespitum.
  • Anoplura e.g. Pediculus humanus capitis, Pediculus humanus corporis, Phthirus pubis.
  • Heteroptera e.g. Cimex hemipterus, Cimex lectularius, Rhodinus prolixus, Triatoma infestans.
  • Application is in aerosols, non-pressurized sprays, e.g. Pump and atomizer sprays, fog machines, foggers, foams, gels, evaporator products with cellulose or plastic evaporator plates, liquid evaporators, gel and membrane evaporators, propeller driven evaporators, energyless or passive evaporation systems, moth papers, moth cakes and moth gels, as granules or dusts, in litter or bait stations.
  • Pump and atomizer sprays e.g. Pump and atomizer sprays, fog machines, foggers, foams, gels, evaporator products with cellulose or plastic evaporator plates, liquid evaporators, gel and membrane evaporators, propeller driven evaporators, energyless or passive evaporation systems, moth papers, moth cakes and moth gels, as granules or dusts, in litter or bait stations.
  • the compounds of the formula (I) according to the invention also have very good antifungal effects. They have a very broad antimycotic spectrum of activity, in particular against dermatophytes and yeasts, mold and diphasic fungi (eg against Candida species such as Candida albicans, Candida glabrata) and Epidermophyton floccosum, Aspergillus species such as Aspergillus niger and Aspergillus fumigatus, Trichophyton species such as Trichophyton mentagrophytes, Microsporon species such as Microsporon canis and audouinü.
  • the enumeration of these fungi is by no means a limitation of the detectable mycotic Spectrum, but has only explanatory character.
  • the active compounds can be used as such, in the form of their formulations or in the use forms prepared therefrom, such as ready-to-use solutions, suspensions, wettable powders, pastes, soluble powders, dusts and granules.
  • the application is done in the usual way, e.g. by pouring, spraying, spraying, scattering, dusting, foaming, brushing, etc. It is also possible to apply the active ingredients by the ultra-low-volume method or to inject the active ingredient preparation or the active ingredient itself into the soil. It can also be the seed of the plants to be treated.
  • the application rates can be varied within a relatively wide range, depending on the mode of administration.
  • the application rates of active ingredient are generally between 0.1 and 10,000 g / ha, preferably between 10 and 1,000 g / ha.
  • the application rates of active ingredient are generally between 0.001 and 50 g per kilogram of seed, preferably between 0.01 and 10 g per kilogram of seed.
  • the application rates of active ingredient are generally between 0.1 and 10,000 g / ha, preferably between 1 and 5,000 g / ha.
  • the THF solution of the acid chloride thus produced is at room temperature (about 20 0 C) to a solution of 1.1 g (8.1 mmol) (2S) -l- (methylthio) propan-2-arnine and 1.13 ml (8.1 mmol) of triethylamine in tetrahydrofuran was added dropwise.
  • the mixture is stirred for 2 h at 60 0 C, then poured into water and extracted several times with dichloromethane.
  • the combined organic phases are dried over sodium sulfate, filtered and concentrated on a rotary evaporator. The remaining solid is stirred with petroleum ether, filtered off with suction and dried.
  • Emulsifier 0.5 part by weight of alkylaryl polyglycol ether
  • active compound 1 part by weight of active compound is mixed with the indicated amounts of solvent and emulsifier, and the concentrate is diluted with emulsifier-containing water to the desired concentration.
  • Chinese cabbage leaf discs (Brassica pekinensis) are sprayed with a preparation of active compound of the desired concentration and, after drying, are populated with larvae of the horseradish leaf beetle (Phaedon cochleariae).
  • the effect is determined in%. 100% means that all beetle larvae have been killed; 0% means that no beetle larvae have been killed.
  • Emulsifier 0.5 part by weight of alkylaryl polyglycol ether
  • active compound 1 part by weight of active compound is mixed with the indicated amounts of solvent and emulsifier, and the concentrate is diluted with emulsifier-containing water to the desired concentration.
  • Maize leaf discs (Zea mays) are sprayed with an active compound preparation of the desired concentration and, after drying, are infested with caterpillars of the armyworm (Spodoptera frugiperda).
  • Emulsifier 1 part by weight of alkylaryl polyglycol ether
  • active compound 1 part by weight of active compound is mixed with the indicated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration.
  • Emulsifier 1 part by weight of alkyl-aryl-polyglycol ether
  • active compound 1 part by weight of active compound is mixed with the indicated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
  • Pyridine Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

L'invention concerne des acrylamides hétérobicycliques de la formule (I) où A1, A2, R1, R2, R3, R4, R5 et R6 ont la signification donnée dans la description, ces acrylamides hétérocycliques permettant de lutter contre des nuisibles. L'invention concerne également de nouveaux acrylamides hétérobicycliques et leur procédé de production de ces matières ainsi que les composés de la formule (IA) où A2, R1, R2, R5 et R6 ont la signification donnée dans la description.
EP06707280A 2005-03-05 2006-02-27 Acrylamide heterobicyclique Withdrawn EP1858899A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE102005010215A DE102005010215A1 (de) 2005-03-05 2005-03-05 Heterobicyclische Acrylamide
PCT/EP2006/001761 WO2006094666A1 (fr) 2005-03-05 2006-02-27 Acrylamide heterobicyclique

Publications (1)

Publication Number Publication Date
EP1858899A1 true EP1858899A1 (fr) 2007-11-28

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EP06707280A Withdrawn EP1858899A1 (fr) 2005-03-05 2006-02-27 Acrylamide heterobicyclique

Country Status (8)

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US (1) US20090118286A1 (fr)
EP (1) EP1858899A1 (fr)
JP (1) JP2008531624A (fr)
CN (1) CN101171255A (fr)
BR (1) BRPI0609253A2 (fr)
DE (1) DE102005010215A1 (fr)
TW (1) TW200700423A (fr)
WO (1) WO2006094666A1 (fr)

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Publication number Priority date Publication date Assignee Title
EP3083643B1 (fr) 2013-12-20 2019-02-27 Syngenta Participations AG Hétérocycles bicycliques 5,5 substitués avec des substituants contenant du soufre ayant une activité pesticide

Family Cites Families (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1215066A (en) * 1968-03-25 1970-12-09 Shell Int Research Acrylamides and their use as fungicides
DE3020421A1 (de) * 1980-05-29 1981-12-10 Bayer Ag, 5090 Leverkusen Imidazoazolalkensaeureamide, neue zwischenprodukte zu ihrer herstellung, ihre herstellung und ihre verwendung in arzneimitteln
US4444770A (en) * 1980-05-29 1984-04-24 Bayer Aktiengesellschaft New imidazoazole-alkenoic acid amide compounds, intermediate products for their production, their production, and their medicinal use
US4525357A (en) * 1980-06-27 1985-06-25 Union Carbide Corporation Derivatives of bicyclic 2-iminothiazolidine oximes
US4264616A (en) * 1980-08-29 1981-04-28 Gulf Oil Corporation 2-Iodoacetylimino-3-methyl-5-trifluoromethyl-1,3,4-thiadiazol-4-ine and use as a fungicide
DE3208437A1 (de) * 1982-03-09 1983-09-15 Bayer Ag, 5090 Leverkusen Imidazothiadiazolalkencarbonsaeureamide, neue zwischenprodukte zu ihrer herstellung, ihre herstellung und ihre verwendung in arzneimitteln
DE3329621A1 (de) * 1983-08-17 1985-02-28 Bayer Ag, 5090 Leverkusen Aminoalkyl-imidazothiadiazol-alkencarbonsaeureamide, neue zwischenprodukte zu ihrer herstellung, ihre herstellung und ihre verwendung in arzneimitteln
DE3502264A1 (de) * 1985-01-24 1986-07-24 Bayer Ag, 5090 Leverkusen Imidazoalkensaeurederivate, ein verfahren zu ihrer herstellung und ihre verwendung fuer die herstellung pharmazeutischer wirkstoffe
ZW3686A1 (en) * 1985-02-18 1987-09-23 Wellcome Found Pesticidal compounds

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO2006094666A1 *

Also Published As

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TW200700423A (en) 2007-01-01
CN101171255A (zh) 2008-04-30
DE102005010215A1 (de) 2006-09-07
WO2006094666A1 (fr) 2006-09-14
BRPI0609253A2 (pt) 2010-03-09
JP2008531624A (ja) 2008-08-14
US20090118286A1 (en) 2009-05-07

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