WO1999010334A1 - 5-aminoisothiazoles acyles a usage de pesticides et de fungicides - Google Patents

5-aminoisothiazoles acyles a usage de pesticides et de fungicides Download PDF

Info

Publication number
WO1999010334A1
WO1999010334A1 PCT/EP1998/005045 EP9805045W WO9910334A1 WO 1999010334 A1 WO1999010334 A1 WO 1999010334A1 EP 9805045 W EP9805045 W EP 9805045W WO 9910334 A1 WO9910334 A1 WO 9910334A1
Authority
WO
WIPO (PCT)
Prior art keywords
alkyl
fluorine
chlorine
substituted
optionally
Prior art date
Application number
PCT/EP1998/005045
Other languages
German (de)
English (en)
Inventor
Markus Heil
Thomas Bretschneider
Gerd Kleefeld
Christoph Erdelen
Klaus Stenzel
Andreas Turberg
Norbert Mencke
Original Assignee
Bayer Aktiengesellschaft
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 Aktiengesellschaft filed Critical Bayer Aktiengesellschaft
Priority to JP2000507663A priority Critical patent/JP2001514175A/ja
Priority to AU92594/98A priority patent/AU9259498A/en
Priority to EP98945190A priority patent/EP1005461A1/fr
Publication of WO1999010334A1 publication Critical patent/WO1999010334A1/fr

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D275/00—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings
    • C07D275/02—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings not condensed with other rings
    • C07D275/03—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings not condensed with other rings 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
    • 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
    • A01N47/08—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 one or more single bonds to nitrogen atoms
    • A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
    • A01N47/18—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing a —O—CO—N< group, or a thio analogue thereof, directly attached to a heterocyclic or cycloaliphatic ring

Definitions

  • the present invention relates to new acylated 5-aminoisothiazoles, processes for their preparation and their use for controlling animal pests and as fungicides.
  • R 1 represents alkyl, haloalkyl, alkoxyalkyl, alkylthioalkyl, alkoxy, alkylthio, alkylamino, dialkylamino or optionally substituted cycloalkyl,
  • R 2 represents hydrogen, halogen, cyano, nitro, thiocyanato, alkoxycarbonyl, alkenyloxycarbonyl, alkylthio, haloalkylthio, alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, haloalkylsulfonyl, thiocarbamoyl, alkoxy, formyl, alkylcarbonyl or for -CR 7 -NOR 8 , where
  • R 7 and R 8 independently of one another are hydrogen, alkyl, haloalkyl, alkenyl, in each case optionally substituted cycloalkyl or cycloalkyl- represent alkyl or optionally substituted aryl or arylalkyl,
  • R 3 for alkyl, haloalkyl, alkoxyalkyl, alkylthioalkyl, alkenyl, alkynyl, alkylcarbonyloxyalkyl, alkoxycarbonyloxyalkyl; for optionally substituted aryl, arylalkyl or aryloxyalkyl; represents in each case optionally substituted cycloalkyl, cycloalkylalkyl, cycloalkoxyalkyl or cycloalkylthioalkyl or for -N CR 5 R 6 , in which
  • R 5 and R 6 independently of one another are hydrogen, alkyl, haloalkyl,
  • Alkenyl in each case optionally substituted cycloalkyl or cycloalkylalkyl or for optionally substituted aryl or arylalkyl, or
  • R 5 and R 6 together with the carbon atom to which they are attached represent an optionally substituted carbocyclic ring
  • R 4 represents optionally substituted aryl, optionally substituted cycloalkyl, optionally substituted cycloalkenyl or an optionally substituted heterocycle,
  • A represents oxygen or sulfur
  • Y stands for optionally substituted alkylene, alkenylene or alkyleneoxy and
  • Z represents oxygen or sulfur.
  • R 1 , R 2 , R 4 and Y have the meaning given above,
  • R 3 , A and Z have the meaning given above and
  • G represents a leaving group, e.g. for halogen (especially chlorine), or imidazolyl,
  • R 4 , Y and G have the meaning given above,
  • the acylated 5-aminoisothiazoles according to the invention show a considerably better activity against animal pests and fungi than the constitutionally similar known compounds
  • R 1 preferably represents C 1 -C 4 -alkyl, C 1 -C 5 -haloalkyl having 1 to 5 identical or different halogen atoms, such as fluorine, chlorine or bromine atoms, CC - alkoxy-C 1 -C 4 -alkyl, C 1 -C 4 - alkylthio-C ⁇ -C 4 alkyl, C, -C 4 -alkoxy, C 4 alkyl thio, C ⁇ -C alkylamino, di (C ⁇ -C4 alkyl) amino, or trisubstituted optionally monosubstituted to, the same or different C 3 -C 6 alkyl or halogen (for example fluorine, chlorine or bromine) substituted C 3 -C 6 cycloalkyl
  • R 2 preferably represents hydrogen, halogen, cyano, nitro, thiocyanato, C 1 -C alkoxycarbonyl, C 2 -C 4 alkenyl
  • R 7 and R 8 independently of one another preferably represent hydrogen, -CC 4 -alkyl, -C -H-haloalkyl having 1 to 5 identical or different halogen atoms, such as fluorine or chlorine atoms, C 2 -C 4 alkenyl; for C 3 -C 6 -cycloalkyl or C 3 -C 6 -cycloalkyl-C 1 -C 6 -alkyl which are each mono- to triple, identical or different, substituted by C 1 -C 4 -alkyl or halogen (for example fluorine, chlorine or bromine); or for in each case monosubstituted to trisubstituted, identically or differently substituted, phenyl or phenyl-C 1 -C 6 -alkyl, where the substituents on the phenyl ring are halogen, nitro, cyano, C 1 -C 8
  • halogen atoms such as fluorine or chlorine atoms, -C-C - alkoxy, CC - alkylthio, CC 2 -haloalkoxy and C ⁇ -C 2 -haloalkylthio
  • R 3 preferably represents Ci-Cg-alkyl, C ⁇ -C haloalkyl having 1 to 5 identical or different halogen atoms, such as fluorine or chlorine atoms, C ⁇ -C 4 alkoxy C ⁇ -C4 alkyl, CC 4 alkylthio C C 4 alkyl, C 2 -C 4 alkenyl, C 2 -C 4 alkynyl, d-
  • R 5 and R 6 independently of one another preferably represent hydrogen, CC alkyl, C 1 -C 4 -haloalkyl having 1 to 5 identical or different
  • Halogen atoms such as fluorine or chlorine atoms, C 2 -C 4 alkenyl; for C 3 -C 6 -cycloalkyl or C 3 -C 6 -cycloalkyl-C 4 -C 4 -alkyl which are optionally monosubstituted to triple, identically or differently, with C 1 -C 6 -alkyl or halogen (for example fluorine, chlorine or bromine); or are each optionally monosubstituted to trisubstituted, identical or differently substituted, phenyl or phenyl-C 1 -C 4 -alkyl, the substituents in each case on the phenyl ring
  • C 2 haloalkylthio each having 1 to 5 identical or different halogen atoms, such as fluorine and chlorine atoms, C 1 -C 4 -alkoxy-carbonyl and C 1 -C 6 -alkyl carbonyloxy come into question, or
  • R 5 and R 6 together with the carbon atom to which they are attached, are preferably a single to triple, identical or different, by -CC 4 -alkyl, C 1 -C -alkoxy or halogen (for example such as fluorine, chlorine or bromine) substituted 5- to 7-membered carbocyclic ring.
  • halogen for example such as fluorine, chlorine or bromine
  • R 9 is C 1 -C 4 alkyl, such as in particular methyl or ethyl; C 1 -C 4 -
  • Alkylcarbonyl such as in particular methylcarbonyl or ethylcarbonyl; or for optionally single or double, identical or different by C 1 -C 4 alkyl, such as in particular methyl or ethyl; Halogen, such as in particular fluorine or chlorine; C ! -C 4 haloalkyl, such as in particular trifluoromethyl; C 1 -C 4 alkoxy, such as in particular methoxy; and C r C 4 - haloalkoxy, in particular trifluoromethoxy substituted phenylsulfonyl;
  • substituents being halogen, nitro, cyano, C 1 -C 4 - alkyl, C 1 -C alkoxy, C 1 -C 4 alkylthio, C 1 -C haloalkyl, C 1 -C 4 haloalkoxy, C ⁇ -C Halogenoalkylthio, optionally single or double, identical or different by C 1 -C 4 alkyl, halogen, C 1 -C haloalkyl, C 1 -C 4 alkoxy or C 1 -C 4 haloalkoxy substituted phenylsulfonyl and in each case optionally monosubstituted to trisubstituted, identically or differently, phenyl, phenoxy, phenylthio or benzyl, the substituents being halogen, nitro, cyano, C r C 4 alkyl, C r C 4 alkoxy, C r C 4 alkylthio, C r C 4 -
  • Y preferably represents oxygen or sulfur.
  • Y preferably represents C 1 -C 6 -alkylene, C 1 -C 6 -hydroxyalkylene, C 1 -C -alkoxy-
  • Halogen is preferably fluorine, chlorine and bromine.
  • Z preferably represents oxygen or sulfur.
  • R 1 particularly preferably represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl; CH 2 F, CHF 2 , CF 3 , CH 2 C1, CH 2 Br, CHC1CH 3 ; Methoxy, ethoxy, methylthio, methylamino, methoxymethyl, ethoxymethyl; Methylthiomethyl or cyclopropyl.
  • R 2 particularly preferably represents hydrogen, chlorine, bromine, cyano, nitro, thiocyanato; Methoxycarbonyl, ethoxycarbonyl, i-propoxycarbonyl, n-prop-oxycarbonyl; Allyloxycarbonyl; CSNH 2 , SCH 3 , SOCH 3 , SO 2 CH 3 , CHO,
  • R 3 particularly preferably represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl; C 1 -C 2 haloalkyl having 1 to 5 identical or different halogen atoms, such as fluorine or chlorine atoms,
  • Phenyl ring substituted phenyl, phenyl -CC 2 -alkyl or phenoxy-C 1 -C 2 -alkyl, where fluorine, chlorine, bromine, nitro, cyano, methyl, ethyl are used as substituents, Trifluoromethyl, methoxy, ethoxy, methylthio, trifluoromethoxy, trifluoromethylthio, methoxycarbonyl, ethoxycarbonyl or methylcarbonyloxy come into question, or for cyclopropyl, cyclopentyl, cyclohexyl, cyclopropylmethyl or cyclopentylmethyl or cyclopentylmethyl, which are optionally monosubstituted to triple, identical or different in the cycloalkyl part , where substituents are methyl, ethyl, n- or i-propyl, fluorine, chlorine and bromine or for -N CR 5 R 6
  • R 5 and R 6 independently of one another particularly preferably represent methyl
  • R 5 and R 6 together with the carbon atom to which they are attached are particularly preferably a carbocyclic six-membered ring which may be mono- or disubstituted, identically or differently, by methyl, ethyl, methoxy, fluorine or chlorine.
  • cyclopentyl, cyclohexyl, cyclopentenyl or cyclohexenyl which have the same or different substitution, fluorine, chlorine, bromine, methyl, ethyl, isopopyl, methoxy, trifluoromethyl and methylcarbonyl being suitable as substituents, or, if appropriate, single to triple, identical or differently substituted phenyl, with fluorine, chlorine, nitro, cyano; Methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl; Methoxy, ethoxy, n- or i- Propoxy; Methylthio; -CF 3 , -CHF 2 , -CH 2 CF 3 , -CH 2 -CF 2 -CHF 2 , -CH (CF 3 ) -CH 3 ; -OCF 3 , -OCHF 2
  • N which can each be substituted by Fluorine, chlorine, nitro, cyano; Methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl; Methoxy, ethoxy, n- or i-propoxy; Methylthio; -CF 3 , CHF 2 , -CH 2 CF 3 , -CH 2 -CF 2 -CHF 2 , -CH (CF 3 ) -CH 3 ; -OCF 3 , -OCHF 2 , -OCH 2 CF 3 , -O-CH 2 -CF 2 -CF 3 , -OCH 2 -CF 2 -CHF 2 , -O-CH (CF 3 ) -CH 3 ; -SCF 3 ; and in each case optionally mono- or disubstituted, identically or differently substituted phenyl, phenoxy or phenylthio,
  • R 9 is C 1 -C 4 alkyl, such as in particular methyl or ethyl; C 1 -C 4 alkylcarbonyl, such as in particular methylcarbonyl or ethylcarbonyl; or for optionally single or double, identical or different by C j -C 4 alkyl, such as in particular methyl or ethyl; Halogen, such as in particular fluorine or chlorine; C 1 -C 4 haloalkyl, such as in particular trifluoromethyl; -C-C 4 alkoxy, such as in particular methoxy; and C J -C 4 - haloalkoxy, such as in particular trifluoromethoxy substituted phenylsulfonyl;
  • R 1 particularly preferably represents oxygen or sulfur.
  • R 1 very particularly preferably represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl; CH 2 F, CHF 2 , CF 3 , CH 2 C1, CH 2 Br, methoxy, ethoxy, methylthio, methylamino or cyclopropyl.
  • R 2 very particularly preferably represents hydrogen, chlorine, bromine, cyano, nitro
  • R 3 very particularly preferably represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl; Chloroethyl; 2,2,2-trifluoroethyl; Methoxymethyl, methoxyethyl;
  • Allyl, propargyl; for phenyl or benzyl which is optionally mono- or disubstituted, identically or differently, in the phenyl ring, fluorine, chlorine, bromine, nitro, cyano, methyl, ethyl, trifluoromethyl, methoxy, ethoxy, trifluoromethoxy, methoxycarbonyl, ethoxycarbonyl or methylcarbonyloxy being suitable as substituents , or for each optionally single or double, identical or different in the cycloalkyl part substituted by methyl, fluorine or chlorine-substituted cyclopropylmethyl, cyclopentylmethyl or cyclohexylmethyl; or for -N R 5 R 6 .
  • R 5 and R 6 independently of one another very particularly preferably represent
  • Fluorine, chlorine, bromine, nitro, cyano, methyl, ethyl, trifluoromethyl, methoxy, ethoxy, trifluoromethoxy, methoxycarbonyl, ethoxycarbonyl or methylcarbonyloxy come into question.
  • R 4 very particularly preferably represents from one to three times, if appropriate
  • Y very particularly preferably represents -CH 2 , -CH (CH 3 ) -, -CH (OCH 3 ) - or -CH (OCOCH 3 ) -.
  • Z very particularly preferably stands for oxygen.
  • Preferred compounds according to the invention are substances of the formulas (IA) or (IB), or (IC):
  • R 1 , R 2 , R 3 , A, Y and Z stand for the abovementioned general, preferred, particularly preferred and very particularly preferred meanings and
  • X 1 , X 2 , X 3 , X 4 and X 5 stand for the substituents mentioned above under R 4 in general, preferably, particularly preferably and very particularly preferably for the phenyl or phenoxy radical and
  • X 1 , X 2 , X 3 and X 4 can also each represent hydrogen.
  • Further preferred groups of compounds are those of the formulas (IA), (IB) or (IC), in which the phenoxy radical para to the N (CZ-AR 3 ) -CO-CH 2 - or N (CZ-AR 3 ) -CO-CH (CH 3 ) group, among these compounds those are particularly preferred in which the substituents X 1 , X 2 , X 3 and X 4 are hydrogen.
  • hydrocarbon radicals such as alkyl or alkenyl - also in connection with heteroatoms such as alkoxy or alkylthio - are in each case straight-chain or branched as far as possible
  • alkyleneoxy or -CH 2 0 is to be understood such that R 4 in formula (I) is linked to the oxygen of the alkyleneoxy or -CH 2 0 radical
  • R 1 C 3 H 7 -i
  • R 1 , R 4 , Y and -CZ-AR 3 as listed in Table 1.
  • R 2 -COOCH 3
  • R 1 , R 4 , Y and -CZ-AR 3 as listed in Table 1.
  • R 1 , R 4 , Y and -CZ-AR 3 as listed in Table 1.
  • R 2 SOCH 3
  • R 1 , R 4 , Y and -CZ-AR 3 as listed in Table 1.
  • R 1 , R 2 , R 4 and -CZ-AR 3 as listed in Table 1.
  • R 1 , R 2 , R 4 and -CZ-AR 3 as listed in Table 1.
  • R 4 - ⁇ " ° CH 2 CF 3
  • R 1 , R 2 , Y and -CZ-AR 3 as listed in Table 1.
  • R 4 _ ⁇ o - ⁇ > - CI
  • R 1 , R 2 , Y and -CZ-AR 3 as listed in Table 1.
  • R 1 , R 2 , Y and -CZ-AR 3 as listed in Table 1.
  • R 1 , R 2 , Y and -CZ-AR 3 as listed in Table 1.
  • R 1 , R 2 , Y and -CZ-AR 3 as listed in Table 1.
  • R 1 , R 2 , Y and -CZ-AR 3 as listed in Table 1.
  • R 1 , R 2 , Y and -CZ-AR 3 as listed in Table 1.
  • R 1 , R 2 , Y and -CZ-AR 3 as listed in Table 1.
  • R 1 , R 2 , Y and -CZ-AR 3 as listed in Table 1.
  • R 1 , R 2 , Y and -CZ-AR 3 as listed in Table 1.
  • R 1 , R 2 , Y and -CZ-AR 3 as listed in Table 1.
  • R 1 , R 2 , Y and -CZ-AR 3 as listed in Table 1.
  • R 1 , R 2 , Y and -CZ-AR 3 as listed in Table 1.
  • R 4 ⁇ 's 0 - ⁇ - N0 2
  • R 1 , R 2 , Y and -CZ-AR 3 as listed in Table 1.
  • R 1 , R 2 , Y and -CZ-AR 3 as listed in Table 1.
  • R 1 , R 2 , Y and -CZ-AR 3 as listed in Table 1.
  • R4 - V ⁇ -OCF 2 CHFCI
  • R 1 , R 2 , Y and -CZ-AR 3 as listed in Table 1.
  • R 1 , R 2 , Y and -CZ-AR 3 as listed in Table 1.
  • R 1 , R 2 , Y and -CZ-AR 3 as listed in Table 1.
  • R 1 , R 2 , Y and -CZ-AR 3 as listed in Table 1.
  • R 4 - ⁇ "0_ 0
  • R 1 , R 2 , Y and -CZ-AR 3 as listed in Table 1.
  • R 1 , R 2 , Y and -CZ-AR 3 as listed in Table 1.
  • R 1 , R 2 , Y and -CZ-AR 3 as listed in Table 2.
  • R 4 as listed in Tables 14 to 38.
  • R 1 , R 2 , Y and -CZ-AR 3 as listed in Table 3.
  • R 4 as listed in Tables 14 to 38.
  • R 1 , R 2 , Y and -CZ-AR 3 as listed in Table 4.
  • R 1 , R 2 , Y and -CZ-AR 3 as listed in Table 5.
  • R 4 as listed in Tables 14 to 38.
  • R 1 , R 2 , Y and -CZ-AR 3 as listed in Table 6.
  • R 4 as listed in Tables 14 to 38.
  • R 1 , R 2 , Y and -CZ-AR 3 as listed in Table 7.
  • R 4 as listed in Tables 14 to 38.
  • R 4 as listed in Tables 14 to 38.
  • R 1 , R 2 , Y and -CZ-AR 3 as listed in Table 9.
  • R 4 as listed in Tables 14 to 38.
  • R 1 , R 2 , Y and -CZ-AR 3 as listed in Table 10.
  • R4 as listed in Tables 14 to 38.
  • Rl and R 2 have the meaning given above
  • the 5-aminoisothiazoles of the formula (VI) are largely known (cf., for example, DE-A 43 28 425, DE-A 22 49 162, WO-A 93/19 054, WO-A 94/21 617 and J. Het. Chem. 1989. 26, 1575) and / or can be prepared by known methods (cf. for example the cited references).
  • R 7 " ⁇ is hydrogen or alkyl, preferably C1-C4-alkyl, such as in particular methyl and
  • R8 has the meaning given above.
  • the 5-aminoisothiazoles of the formula (VI A) can be prepared in a generally known manner and
  • R, R 8 and R stand for the general, preferred, particularly preferred and very particularly preferred meanings mentioned above.
  • the 5-aminoisothiazoles of the formula (VI B) are known (see, for example, J. Het. Chem. 1989, 26, 1575.) and / or can be prepared by known methods.
  • the further compounds of formula (V) to be used as starting materials in process (b) according to the invention are generally known compounds of organic chemistry.
  • the processes (a) and (b) described above for the preparation of the compounds of the formula (I) are preferably carried out in the presence of a diluent. All customary solvents can be used as diluents.
  • Halogenated aliphatic or aromatic hydrocarbons, ethers or nitriles such as e.g. Cyclohexane, toluene, chlorobenzene, choroform, dichloromethane, dichloroethane, dioxane, tetrahydrofuran, diethyl ether or acetonitrile.
  • Formula (I) are carried out in the presence of a base (cf. also Chem. Ber. 95, 829 (1965); Liebigs Ann. Chem. 739, 201 (1970) and 636 (1973)).
  • Alkali or alkaline earth carbonates or bicarbonates or nitrogen bases examples include sodium hydroxide, calcium hydroxide, potassium carbonate, sodium hydrogen carbonate, triethylamine, dibenzylamine, diisopropylamine, pyridine, quinoline, diazabicyclooctane (DABCO), diazabicyclonones (DBN) and diazabicycloundecene (DBU).
  • DABCO diazabicyclooctane
  • DBN diazabicyclonones
  • DBU diazabicycloundecene
  • reaction temperatures can be varied within a wide range in the processes (a) and (b) described. In general, temperatures between -40 ° C and + 200 ° C, preferably between -10 ° C and 100 ° C.
  • insects in particular insects, arachnids and nematodes, which occur in agriculture, in forests, in the protection of stored products 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.
  • Symphyla e.g. Scutigerella immaculata.
  • Thysanura e.g. Lepisma saccharina.
  • Hymenoptera e.g. Diprion spp., Hoplocampa spp., Lasius spp., Monomorium pharaonis, Vespa 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.
  • 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., Pvadopholus similis, Ditylenchus dipsaci, Tylenchulus semipenetrans, Heterodera spp., Globodera spp., Meloidogyne spp., Aphelenchoides spp., Longidorus spp., Xiphinema spp., Trichodorus spp ..
  • the compounds of the formula (I) according to the invention are particularly notable for high insecticidal activity.
  • insects which damage plants such as, for example, against the peach aphid (Myzus persicae), the green rice leafhopper (Nephotettix cincticeps), the larvae of the horseradish beetle (Phaedon cochleariae) and the caterpillars of the owl butterfly (Spodoptera frugiperda).
  • the active ingredients can be converted into the customary formulations, such as solutions, emulsions, wettable powders, suspensions, powders, dusts, pastes, soluble powders, granules, suspension emulsion concentrates, impregnated with active ingredients
  • Natural and synthetic substances as well as very fine encapsulation in polymeric substances are prepared in a known manner, for example by mixing the active ingredients with extenders, that is to say liquid solvents and / or solid carriers, optionally using surface-active agents, that is to say emulsifiers and / or dispersants and / or foam-generating agents.
  • extenders that is to say liquid solvents and / or solid carriers
  • surface-active agents that is to say emulsifiers and / or dispersants and / or foam-generating agents.
  • organic solvents can also be used as auxiliary solvents.
  • auxiliary solvents e.g. organic solvents
  • aromatics such as xylene, toluene, or alkylnaphthalenes
  • chlorinated aromatics and chlorinated aliphatic hydrocarbons such as chlorobenzenes, chlorethylenes or methylene chloride
  • aliphatic hydrocarbons such as cyclohexane or paraffins, e.g.
  • Petroleum fractions mineral and vegetable oils, alcohols such as butanol or glycol 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.
  • Possible solid carriers are: e.g. Ammonium salts and natural rock powders such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and synthetic rock powders such as highly disperse silica, aluminum oxide or silicates are suitable as solid carriers for granules: e.g. broken or fractionated natural rocks such as calcite, marble, pumice, sepiolite, dolomite and synthetic granules from inorganic or organic flours and granules from organic material such as sawdust, coconut shells, corn cobs and tobacco stems; as emulsifying and / or foaming agents are possible: e.g. non-ionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene
  • Fatty alcohol ethers e.g. Alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates and protein hydrolyzates; Possible dispersants are: e.g. Lignin sulfite liquor and methyl cellulose.
  • Adhesives such as carboxymethyl cellulose, natural and synthetic powdery, granular or latex-shaped polymers, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, and natural phospho- lipids such as cephalins and lecithins and synthetic phospholipids.
  • Other additives can be mineral and vegetable oils.
  • Dyes such as inorganic pigments, e.g. Iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin, azo and metal phthalocyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc can be used.
  • the formulations generally contain between 0.1 and 95% by weight of active compound, preferably between 0.5 and 90%.
  • the active substance according to the invention can be present in its commercially available formulations and in the use forms prepared from these formulations in a mixture with other active substances, such as insecticides, attractants, sterilants, bactericides, acaricides, nematicides, fungicides, growth-regulating substances or herbicides.
  • Insecticides include, for example, phosphoric acid esters, carbamates, carboxylic acid esters, chlorinated hydrocarbons, phenylureas, substances produced by microorganisms, etc.
  • Debacarb dichlorophene, diclobutrazole, diclofluanide, diclomezin, dicloran, diethofencarb, difenoconazole, dimethirimol, dimethomorph, diniconazole, diniconazol-M, dinocap, diphenylamine, dipyrithione, ditalimfos, dithorphoxinodonine, dithorphononodine
  • Famoxadone, fenapanil, fenarimol, fenbuconazole, fen assumes that it is not limited to: azinam, flumetover, fluoromid, fluquinconazole, flurprimolol, flusulfazolutin, flusulfazolutol, flusulfazolutol, flusulfazolutol, flusulfazolutol, flusulfazolutol, flusulfazolutol, flusulfazolutol, flusulfazolutol, flusulfazolutol, flusulfazolutol, flusulfazolutol, flusulfazolutol, flusulfazolutol, flusulfazolutol, flusulfazolutol, flusulfazolutol, flusulfazolutol, flusulfazolu
  • Imazalil Imibenconazol, Iminoctadin, Iminoctadinealbesilat, Iminoctadinetriacetat, Iodocarb, Ipconazol, Iprobefos (EBP), Iprodione, Irumamycin, Isoprothiolan, Isovaledione,
  • Mancopper Mancozeb, Maneb, Meferimzone, Mepanipyrim, Mepronil, Metalaxyl,
  • Metconazole methasulfocarb, meth hyporoxam, metiram, metomeclam, metsulfovax, mildiomycin, myclobutanil, myclozolin, Nickel dimethyldithiocarbamate, nitrothal isopropyl, Nuarimol,
  • Tebuconazole Tebuconazole, tecloftalam, tecnazen, tetcyclacis, tetraconazole, thiabendazole,
  • Thicyofen Thifluzamide, Thiophanate-methyl, Thiram, Tioxymid, Tolclofos-methyl, Tolylfluanid, Triadimefon, Triadimenol, Triazbutil, Triazoxid, Trichlamid, Tricyclazol, Tridemorph, Triflumizol, Triforin, Triticonazole,
  • Fenamiphos Fenazaquin, Fenbutatinoxid, Fenitrothion, Fenobucarb, Fenothiocarb, Fenoxycarb, Fenpropathrin, Fenpyrad, Fenpyroximat, Fenthion, Fenvalerate, Fipronil, Fluazinam, Flucycloxuron, Flucythrinat, Flufenoxuron, Flufenatex, Fluufenate, Fluufenprox
  • Fonophos Formothion, Fosthiazat, Fubfenprox, Furathiocarb, HCH, heptenophos, hexaflumuron, hexythiazox,
  • Mecarbam Mevinphos, Mesulfenphos, Metaldehyde, Methacrifos, Methamidophos, Methidathion, Methiocarb, Methomyl, Metolcarb, Milbemectin, Monocrotophos, Moxidectin,
  • Parathion A Parathion M, Permethrin, Phenthoat, Phorat, Phosalon, Phosmet,
  • Tebufenozid Tebufenpyrad
  • Tebupirimiphos Teflubenzuron, Tefluthrin, Temephos, Terbam, Terbufos, Tetrachlorvinphos, Thiafenox, Thiodicarb, Thiofanox, Thio-methon, Thionazin, Thuringiensin, Tralomenhrononium, Triomenethriazonium, Triomenethriazonium, Triomenethriazonium, Tri
  • the active compounds according to the invention can also be prepared in their commercially available formulations and in those formulated from these formulations
  • Synergists are compounds through which the action of the active ingredients is increased without the added synergist itself having to be active.
  • the active substance content of the use forms prepared from the commercially available formulations can vary within wide ranges.
  • the active substance concentration of the use forms can be from 0.0000001 to 95% by weight of active substance, preferably between 0.0001 and 1% by weight.
  • the application takes place in a customary manner adapted to the application forms
  • the active ingredient When used against hygiene pests and pests of stored products, the active ingredient is distinguished by an excellent residual action on wood and clay as well as a good stability to alkali on limed substrates.
  • the active compounds according to the invention act not only against plant, hygiene and stored-product pests, but also in the veterinary sector against animal parasites (ectoparasites) such as tick ticks, leather ticks, mites, running mites, flies (stinging and licking), parasitic fly larvae, lice,
  • animal parasites ectoparasites
  • tick ticks leather ticks
  • mites running mites
  • flies stinging and licking
  • parasitic fly larvae lice
  • Anoplurida for example Haematopinus spp., Linognathus spp., Pediculus spp., Phtirus spp., Solenopotes spp ..
  • Mallophagida and the subordinates Amblycerina and Ischnocerina for example Trimenopon spp., Menopon spp., Trinoton spp., Bovicola spp., Werneckiella spp., Lepikentron spp., Damalina spp., Trichodectes spp., Felicola spp ..
  • Nematocerina and Brachycerina e.g. Aedes spp., Anopheles spp., Culex spp., Simulium spp., Eusimulium spp., Phlebotomus spp., Lutzomyia spp., Culicoides spp., Chrysops spp., Hybomitra spp., Atylotus spp., Tabanus spp., Haematopota ., Philipomyia spp., Braula spp., Musca spp., Hydrotaea spp., Stomoxys spp., Haematobia spp., Morellia spp., Fannia spp., Glossina spp., Calliphora spp., Glossina spp., Calliphora spp., Glossina spp.,
  • Siphonaptrida e.g. Pulex spp., Ctenocephalides spp., Xenopsylla spp., Ceratophyllus spp ..
  • Actinedida Prostigmata
  • Acaridida e.g. Acarapis spp., Cheyletiella spp., Ornitrocheyletia spp., Myobia spp., Psorergates 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, horses, pigs, donkeys, camels, buffalo, rabbits, chickens, turkeys, ducks, geese, bees, other pets such as e.g. Dogs, cats, house birds, aquarium fish and so-called experimental animals, such as Infest hamsters, guinea pigs, rats and mice.
  • arthropods e.g. Cattle, sheep, goats, horses, pigs, donkeys, camels, buffalo, rabbits, chickens, turkeys, ducks, geese, bees, other pets such as e.g. Dogs, cats, house birds, aquarium fish and so-called experimental animals, such as Infest hamsters, guinea pigs, rats and mice.
  • the active 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, capsules, drinkers, drenches, granules, pastes, boluses, the feed-through method, suppositories, by parenteral administration, for example by Injections
  • implants by nasal application, by dermal application in the form of, for example, diving or bathing (dipping), spraying (spray), pouring on (pour-on and spot-on), washing, powdering and with the aid of shaped articles containing active ingredients, such as collars, ear tags, tail tags, limb tapes, holsters, marking devices, etc.
  • active ingredients such as collars, ear tags, tail tags, limb tapes, holsters, marking devices, etc.
  • Formula (I) as formulations for example powders, emulsions, flowable agents
  • formulations for example powders, emulsions, flowable agents
  • active compounds in an amount of 1 to 80% by weight, directly or after
  • Termites such as Kalotermes flavicollis, Cryptotermes brevis, Heterotermes indicola, Reticulitermes flavipes, Reticulitermes santonensis, Reticulitermes lucihegus, Mastotermes darwiniensis, Zootermopsis nevadensis, Coptotermes formosanus.
  • Bristle tails 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 one to be protected against insect attack is very particularly preferably
  • Wood and wood processing products which can be protected by the agent according to the invention or mixtures containing it are to be understood as examples of construction timber, wooden beams, railway sleepers, bridge parts, jetties, wooden vehicles, boxes, pallets, containers, telephone masts, wooden cladding, wooden windows and doors, plywood , Chipboard, carpentry or wood products that are used in general in house construction or joinery
  • the active ingredients 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, for example 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 as well as other 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 the occurrence of the insects and on the medium. The optimum amount can be determined in each case by use of test series. In general, however, it is sufficient 0.0001 to 20% by weight, preferably 0.001 up to 10% by weight of the active ingredient, based on the material to be protected
  • organic-chemical solvent or solvent mixture and / or an oily or oil-like difficultly 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 agents are preferably oily or oil-like 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 difficultly volatile, water-insoluble, oily and oil-like solvents.
  • Mineral oils with a boiling range of 170 to 220 ° C, test gasoline with a boiling range of 170 to 220 ° C, spindle oil with a boiling range of 250 to 350 ° C, petroleum or aromatics with a boiling range of 160 to 280 ° C, turpentine oil are advantageous and the like for use.
  • Evaporation rate above 35 and a flash point above 30 ° C, preferably above 45 ° C can be partially replaced by slightly or medium volatile organic chemical solvents, with the proviso that the solvent mixture also has an evaporation number above 35 and a flash point above 30 ° C, preferably above 45 ° C, and that the insecticide-fungicide mixture is soluble or emulsifiable in this solvent mixture.
  • Solvents or solvent mixtures replaced by an aliphatic polar organic-chemical solvent or solvent mixture.
  • Aliphatic hydroxyl and / or ester and / or ether groups are preferably used organic chemical solvents such as glycol ether, ester or the like. For use.
  • the organic-chemical binders used 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 are used.
  • the synthetic resin used as a binder can be used in the form of an emulsion, dispersion or solution. Bitumen or bituminous substances up to 10% by weight can also be used as binders. In addition, known dyes, pigments, water-repellants, odor correctors and inhibitors or anticorrosive agents and the like can be used.
  • At least one alkyd resin or modified alkyd resin and / or a drying vegetable oil is preferably contained in the agent or in the concentrate as the organic chemical binder.
  • Alkyd resins with an oil content of more than 45% by weight, preferably 50 to 68% by weight, are preferably used according to the invention.
  • binder mentioned can be replaced by a fixing agent (mixture) or a plasticizer (mixture). These additives are intended to prevent volatilization of the active ingredients and crystallization or precipitation. They preferably replace 0.01 to 30% of the binder (based on 100% of the binder used).
  • the plasticizers come from the chemical classes of phthalic acid esters such as dibutyl, dioctyl or benzyl butyl phthalate, phosphoric acid esters such as tributyl phosphate, adipic acid esters such as di- (2-ethylhexyl) adipate, stearates such as butyl stearate or amyl stearate, oleates such as butyl oleate, higher glycerol glycol or glycerol glycol - ether, 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
  • stearates such as
  • 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, optionally in a mixture with one or more of the above-mentioned organic chemical solvents or diluents, emulsifiers and dispersants.
  • a particularly effective wood protection is achieved through industrial impregnation processes, e.g. Vacuum, double vacuum or pressure process.
  • the ready-to-use compositions can optionally contain further insecticides and, if appropriate, one or more fungicides.
  • 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.
  • Insecticides such as chlorpyriphos, phoxime, silafluofin, alphamethrin, cyfluthrin, cypermethrin, deltamethrin are particularly preferred mixing partners.
  • the active compounds according to the invention also have a strong microbicidal action and can be used practically to combat unwanted microorganisms.
  • the active ingredients are suitable for use as crop protection agents, in particular as fungicides.
  • Fungicidal agents in crop protection are used to combat plasmidiophoromycetes, Oomycetes, Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes, Deuteromycetes.
  • Bactericidal agents are used in crop protection to combat Pseudomonadaeae, Rhizobiaceae, Enterobacteriaceae, Corynebacteriaceae and Streptomycetaceae.
  • Xanthomonas species such as, for example, Xanthomonas campestris pv. Oryzae;
  • Pseudomonas species such as, for example, Pseudomonas syringae pv. Lachrymans;
  • Erwinia species such as, for example, Erwinia amylovora
  • Pythium species such as, for example, Pythium ultimum
  • Phytophthora species such as, for example, Phytophthora infestans
  • Pseudoperonospora species such as, for example, Pseudoperonospora humuli or
  • Plasmopara species such as, for example, Plasmopara viticola
  • Bremia species such as, for example, Bremia lactucae
  • Peronospora species such as, for example, Peronospora pisi or P. brassicae;
  • Erysiphe species such as, for example, Erysiphe graminis
  • Sphaerotheca species such as, for example, Sphaerotheca Sportsiginea;
  • Podosphaera species such as, for example, Podosphaera leucotricha
  • Venturia species such as, for example, Venturia inaequalis
  • Pyrenophora species such as, for example, Pyrenophora teres or P. graminea
  • Cochliobolus species such as, for example, Cochliobolus sativus
  • Drechslera (Conidial form: Drechslera, Syn: Helminthosporium);
  • Uromyces species such as, for example, Uromyces appendiculatus
  • Puccinia species such as, for example, Puccinia recondita
  • Sclerotinia species such as, for example, Sclerotinia sclerotiorum
  • Tilletia species such as, for example, Tilletia caries
  • Ustilago species such as, for example, Ustilago nuda or Ustilago avenae;
  • Pellicularia species such as, for example, Pellicularia sasakii;
  • Pyricularia species such as, for example, Pyricularia oryzae
  • Fusarium species such as, for example, Fusarium culmorum
  • Botrytis species such as, for example, Botrytis cinerea
  • Septoria species such as, for example, Septoria nodorum
  • Leptosphaeria species such as, for example, Leptosphaeria nodorum;
  • Cercospora species such as, for example, Cercospora canescens; Alternaria species, such as, for example, Alternaria brassicae;
  • Pseudocercosporella species such as, for example, Pseudocercosporella herpotrichoides.
  • the active compounds according to the invention can be used as such in
  • the seeds of the plants can also be treated.
  • the active compound concentrations in the use forms can be varied within a substantial range: they are generally between 1 and 0.0001% by weight, preferably between 0.5 and 0.001% by weight.
  • amounts of active ingredient of 0.001 to 50 g per kilogram of seed, preferably 0.01 to 10 g, are generally required.
  • active ingredient concentrations of 0.00001 to 0.1% by weight, preferably 0.0001 to 0.02% by weight, are required at the site of action.
  • 0.18 g (5.90 mmol) is added in portions to a solution of 1.50 g (3.90 mmol) of 4-chloro-5- [4- (4-cyano) phenoxy] phenylacetylamino-3-methylisothiazole in 15 ml of tetrahydrofuran. Added sodium hydride and the solution was stirred for 15 minutes at room temperature. The mixture is then cooled to -5 ° C. and a solution of 0.71 g (5.90 mmol) of allyl chloroformate in 2 ml of tetrahydrofuran is added dropwise.
  • Emulsifier 1 part by weight of alkylaryl polyglycol ether
  • Cabbage leaves (Brassica oleracea), which are heavily infested with peach aphids (Myzus persicae), are treated by being dipped into the preparation of active compound of the desired concentration.
  • the death rate is determined in percent. 100% means that all aphids have been killed, 0% means that no aphids have been killed.
  • Solvent 7 parts by weight of dimethylformamide emulsifier: 1 part by weight of alkylaryl polyglycol ether
  • active compound 1 part by weight of active compound is mixed with the stated amount of solvent and the stated amount of emulsifier, and the concentrate is diluted with water to the desired concentration.
  • Rice seedlings (Oryza sativa) are treated by dipping into the active ingredient preparation of the desired concentration and populated with the green rice leafhopper (Nephotettix cincticeps) while the seedlings are still moist.
  • the death rate is determined in%. 100% means that all cicadas have been killed; 0% means that no cicadas have been killed.
  • the compounds of preparation examples 3, 4, 5 and 8 with an exemplary active compound concentration of 0.1% caused a death rate of 100% after 6 days.
  • Emulsifier 1 part by weight of alkylaryl polyglycol ether
  • Cabbage leaves (Brassica oleracea) are treated by being dipped into the preparation of active compound of the desired concentration and populated with larvae of the horseradish beetle (Phaedon cochleariae) while the leaves are still moist.
  • the death rate is determined in%. 100% means that all beetle larvae have been killed; 0% means that no beetle larvae have been killed.
  • the compounds of preparation examples 3, 4, 5 and 8 with an exemplary active ingredient concentration of 0.1% caused 100% death after 7 days.
  • Emulsifier 1 part by weight of alkylaryl polyglycol ether
  • Cabbage leaves (Brassica oleracea) are treated by being dipped into the preparation of active compound of the desired concentration and populated with caterpillars of the owl butterfly (Spodoptera frugiperda) while the leaves are still moist.
  • the death rate is determined in%. 100% means that all caterpillars have been killed; 0% means that no caterpillars have been killed.
  • the compounds of preparation examples 3, 4, 5 and 8 with an exemplary active ingredient concentration of 0.1% caused 100% death after 7 days.
  • Test animals adult bred females
  • the test is carried out in 5-fold determination. 1 ⁇ l of the solution is injected into the abdomen, the animals are transferred to dishes and stored in an air-conditioned room. The effect is determined by the inhibition of egg laying. 100% means that no tick has laid.
  • the compound according to preparation example 3 with an exemplary activity concentration of 20 ⁇ g / animal, caused a degree of killing of 100%.
  • Test animals Lucilia cuprina larvae
  • test tube which contains approx. 1 cm 3 horse meat and 0.5 ml of the active ingredient preparation.
  • the effectiveness of the active substance preparation is determined after 24 hours and 48 hours.
  • the test tubes are transferred to the beaker with a sand-covered bottom. After a further 2 days, the test tubes are removed and the dolls are counted.
  • the effect of the preparation of active substance is assessed according to the number of flies hatched after 1.5 times the development time of an untreated control. 100% means that no flies have hatched; 0% means that all flies hatched normally.
  • Test animals Blattella germanica or Periplaneta americana
  • test animals are immersed in the drug preparation to be tested for 1 minute. After being transferred to a plastic cup and stored for 7 days in an air-conditioned room, the degree of destruction is determined.
  • the compound according to preparation example 3 with an exemplary active substance concentration of 100 ppm, caused a degree of destruction of 100%.
  • Emulsifier 3 parts by weight of alkylaryl polyglycol ether
  • active compound 1 part by weight of active compound is mixed with the stated amount of solvent and emulsifier and the concentrate is diluted with water to the desired concentration.
  • Evaluation is carried out 10 days after the inoculation. 0% means an efficiency that corresponds to that of the control, while an efficiency of 100% means that no infection is observed.
  • the compound of preparation example 7 achieved an efficiency of 97% at an exemplary application rate of 100 g / ha each.
  • Emulsifier 3 parts by weight of alkylaryl polyglycol ether
  • active compound 1 part by weight of active compound is mixed with the stated amount of solvent and emulsifier and the concentrate is diluted with water to the desired concentration.
  • the compounds of preparation examples 3 and 7 achieve an efficiency of 100% each at an exemplary application rate of 100 g / ha.
  • the plants are then placed in the greenhouse at about 21 ° C. and a relative humidity of about 90%
  • the compound of preparation example 7 achieved an efficiency of 100% at an exemplary application rate of 100 g / ha.

Landscapes

  • Life Sciences & Earth Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Environmental Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Plant Pathology (AREA)
  • Pest Control & Pesticides (AREA)
  • Agronomy & Crop Science (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Thiazole And Isothizaole Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

La présente invention concerne de nouveaux 5-aminoisothiazoles acylés de la formule (1), où R?1, R2, R3, R4¿, A, Y et Z ont la signification indiquée dans la description, leur mode de production ainsi que leur utilisation pour combattre les parasites animaux et comme fongicides.
PCT/EP1998/005045 1997-08-22 1998-08-08 5-aminoisothiazoles acyles a usage de pesticides et de fungicides WO1999010334A1 (fr)

Priority Applications (3)

Application Number Priority Date Filing Date Title
JP2000507663A JP2001514175A (ja) 1997-08-22 1998-08-08 有害生物防除剤並びに殺菌・殺カビ剤としてのアシル化された５−アミノイソチアゾール類
AU92594/98A AU9259498A (en) 1997-08-22 1998-08-08 Acylated 5-aminoisothiazoles as pesticides and fungicides
EP98945190A EP1005461A1 (fr) 1997-08-22 1998-08-08 5-aminoisothiazoles acyles a usage de pesticides et de fungicides

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19736545.0 1997-08-22
DE19736545A DE19736545A1 (de) 1997-08-22 1997-08-22 Acylierte 5-Aminoisothiazole

Publications (1)

Publication Number Publication Date
WO1999010334A1 true WO1999010334A1 (fr) 1999-03-04

Family

ID=7839825

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP1998/005045 WO1999010334A1 (fr) 1997-08-22 1998-08-08 5-aminoisothiazoles acyles a usage de pesticides et de fungicides

Country Status (7)

Country Link
EP (1) EP1005461A1 (fr)
JP (1) JP2001514175A (fr)
AR (1) AR015152A1 (fr)
AU (1) AU9259498A (fr)
DE (1) DE19736545A1 (fr)
WO (1) WO1999010334A1 (fr)
ZA (1) ZA987585B (fr)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2001036415A1 (fr) * 1999-11-18 2001-05-25 Novartis Ag Composes pesticides aminoheterocyclamide
WO2001090105A1 (fr) * 2000-05-25 2001-11-29 Syngenta Limited Isothiazoles utilises en tant que pesticides

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2014527A1 (fr) * 1968-07-06 1970-04-17 Merck Ag E
EP0334809A2 (fr) * 1988-03-21 1989-09-27 Ciba-Geigy Ag Agents pour la protection de plantes contre des maladies
EP0623282A1 (fr) * 1993-05-05 1994-11-09 Shell Internationale Researchmaatschappij B.V. Procédés et composés pesticides
WO1995031448A1 (fr) * 1994-05-17 1995-11-23 Dowelanco Pesticides de n-(5-isothiazolyle)amide
DE19542372A1 (de) * 1995-11-14 1997-05-15 Bayer Ag Acylierte 5-Aminoisothiazole

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2014527A1 (fr) * 1968-07-06 1970-04-17 Merck Ag E
EP0334809A2 (fr) * 1988-03-21 1989-09-27 Ciba-Geigy Ag Agents pour la protection de plantes contre des maladies
EP0623282A1 (fr) * 1993-05-05 1994-11-09 Shell Internationale Researchmaatschappij B.V. Procédés et composés pesticides
WO1995031448A1 (fr) * 1994-05-17 1995-11-23 Dowelanco Pesticides de n-(5-isothiazolyle)amide
DE19542372A1 (de) * 1995-11-14 1997-05-15 Bayer Ag Acylierte 5-Aminoisothiazole

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2001036415A1 (fr) * 1999-11-18 2001-05-25 Novartis Ag Composes pesticides aminoheterocyclamide
AU764228B2 (en) * 1999-11-18 2003-08-14 Novartis Ag Pesticidal aminoheterocyclamide compounds
WO2001090105A1 (fr) * 2000-05-25 2001-11-29 Syngenta Limited Isothiazoles utilises en tant que pesticides

Also Published As

Publication number Publication date
AR015152A1 (es) 2001-04-18
ZA987585B (en) 1999-02-23
DE19736545A1 (de) 1999-02-25
AU9259498A (en) 1999-03-16
EP1005461A1 (fr) 2000-06-07
JP2001514175A (ja) 2001-09-11

Similar Documents

Publication Publication Date Title
EP0877741B1 (fr) 5-amino-1,2,4-thiadiazoles acyles utilises comme pesticides et fongicides
WO1997028133A1 (fr) 4-amino- et 4-hydrazinopyrimidines acylees et leur utilisation comme agents pour lutter contre les parasites
WO1998003474A1 (fr) Derives d&#39;acide glyoxylique
WO2000020415A1 (fr) Heterocyclylamides d&#39;acide phenylacetique ayant un effet insecticide
WO1999062886A1 (fr) 3-thiocarbamoylpyrazoles substitues
EP1047689A1 (fr) Derives de guanidine substitues
EP1097128B1 (fr) Derives d&#39;imidamide
EP1003726A1 (fr) Nitrophenyle-sulfonyle-imidazoles et leur utilisation pour lutter contre des parasites vegetaux et animaux
WO1999010334A1 (fr) 5-aminoisothiazoles acyles a usage de pesticides et de fungicides
EP1144407B1 (fr) Derives de guanidine cycliques et leur utilisation comme pesticides
EP1506164A1 (fr) Derives de n -cyano-n-methyl-imidamide
DE19924273A1 (de) Imidamid-Derivate
EP0906016A1 (fr) Utilisation de pyrrolopyrimidines pour lutter contre des parasites
WO1999000375A1 (fr) Aminoheterocyclylamides substitues
DE19629463A1 (de) Glyoxylsäurethioamide
DE19629466A1 (de) Acylglyoxylsäureoxime
EP0973751A1 (fr) Derives de phenylaminosulfonyluree en tant que fongicide et pesticide
EP1037879A1 (fr) Derives de pyridine condenses
WO1998023600A1 (fr) 4-cyclohexylphenyloxazolines et leur utilisation pour combattre les parasites animaux
DE19750402A1 (de) Acylierte 4-Amino-pyridine

Legal Events

Date Code Title Description
AK Designated states

Kind code of ref document: A1

Designated state(s): AL AM AT AU AZ BA BB BG BR BY CA CH CN CU CZ DE DK EE ES FI GB GE GH GM HR HU ID IL IS JP KE KG KP KR KZ LC LK LR LS LT LU LV MD MG MK MN MW MX NO NZ PL PT RO RU SD SE SG SI SK SL TJ TM TR TT UA UG US UZ VN YU ZW

AL Designated countries for regional patents

Kind code of ref document: A1

Designated state(s): GH GM KE LS MW SD SZ UG ZW AM AZ BY KG KZ MD RU TJ TM AT BE CH CY DE DK ES FI FR GB GR IE IT LU MC NL PT SE BF BJ CF CG CI CM GA GN GW ML MR NE SN TD TG

DFPE Request for preliminary examination filed prior to expiration of 19th month from priority date (pct application filed before 20040101)
121 Ep: the epo has been informed by wipo that ep was designated in this application
WWE Wipo information: entry into national phase

Ref document number: 1998945190

Country of ref document: EP

WWE Wipo information: entry into national phase

Ref document number: 09485514

Country of ref document: US

NENP Non-entry into the national phase

Ref country code: KR

WWP Wipo information: published in national office

Ref document number: 1998945190

Country of ref document: EP

REG Reference to national code

Ref country code: DE

Ref legal event code: 8642

NENP Non-entry into the national phase

Ref country code: CA

WWW Wipo information: withdrawn in national office

Ref document number: 1998945190

Country of ref document: EP