DE19628569A1 - Substituted N- (5-isothiazolyl) thioamides - Google Patents

Abstract

The present invention concerns new N-(5-isothiazolyl) thioamides of the formula (I) in which R<1>, R<2>, R<3>, R<4>, and Y have the meanings given in the description, methods of manufacturing them, and their use to combat animal pests.

Description

The present invention relates to new substituted N- (5-isothiazolyl) thioamides, Process for their preparation and their use in combating animal pests.

It is already known that certain N- (5-isothiazolyl) amides are insecticidal have properties (cf., for example, WO 95/31 448 and the German patent application the applicant with the file number 195 42 372.0 dated November 13, 1995).

However, the effectiveness and range of action of these compounds is particular not always fully satisfied at low application rates and concentrations posed.

New substituted N- (isothiazolyl) thioamides of the formula (I) have been found

in which
R¹ represents alkyl, haloalkyl, alkoxyalkyl, alkylthioalkyl, alkoxy, alkylthio or optionally substituted cycloalkyl,
R² represents hydrogen-halogen, cyano, nitro, thiocyanato, alkoxycarbonyl, alkenyloxycarbonyl, alkylthio, haloalkylthio, alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, haloalkylsulfonyl or thiocarbamoyl,
R³ represents hydrogen, alkyl, haloalkyl, alkoxyalkyl, alkylcarbonyl, alkyl sulfonyl, in each case optionally substituted arylcarbonyl, arylsulfonyl or arylalkyl or optionally substituted cycloalkyl,
R⁴ represents optionally substituted aryl, optionally substituted cycloalkyl or optionally substituted cycloalkenyl and
Y represents optionally substituted alkylene, alkenylene or alkyleneoxy.

It has also been found that the compounds of the formula (I) are obtained when one

• A) compounds of the formula (II) in which
  R¹, R² and R³ have the meaning given above,
  • a) with compounds of the formula (III) R⁴-Y-CS-G (III) in which
    R⁴ and Y have the meaning given above and
    G represents a leaving group, e.g. B. for halogen (in particular chlorine), imidazolyl, benzimidazolyl, 1,2,4-triazolyl, pyrazolyl or benzotriazolyl,
    or
  • b) with dithioesters of the formula (IV) Alk-S-CS-Y-R⁴ (IV) in which
    R⁴ and Y have the meaning given above and
    Alk represents alkyl (e.g. methyl or ethyl) or CH₂COOM, where
    M represents an alkali metal (e.g. sodium or potassium),
    optionally in the presence of a base and optionally in the presence of a diluent;
    or
• B) Compounds of the formula (V) in which
  R¹, R², R³, R⁴ and Y have the meaning given above,
  with a sulfurizing agent, if appropriate in the presence of a diluent.

Finally, it was found that the new compounds of formula (I) are strong possess pronounced biological properties and above all for combating of animal pests, especially insects, arachnids and nema deaths in agriculture, in the forests, in the protection of supplies and materials as well as in the hygiene sector are suitable.

The substituted N- (5-isothiazol-yl) thioamides according to the invention surprisingly show a significantly better effectiveness against animal pests gene as the constitutionally similar known compounds.

The compounds according to the invention are generally defined by the formula (I).  

Preferred substituents or ranges of those in the above and below radicals mentioned formulas are explained below.

R¹ is preferably C₁-C₄-alkyl, C₁-C₄-haloalkyl with 1 to 5 of the same or various halogen atoms, such as fluorine, chlorine and bromine atoms, C₁-C₄-alkoxy-C₁-C₄-alkyl, C₁-C₄-alkylthio-C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₄-alkylthio or for optionally single to triple, the same or differently substituted by C₁-C₄-alkyl or halogen C₃-C₆-cyclo alkyl.

R² preferably represents hydrogen, halogen, cyano, nitro, thiocyanato, C₁- C₄-alkoxy-carbonyl, C₂-C₄-alkenyloxy-carbonyl, C₁-C₄-alkylthio, C₁-C₄- Haloalkylthio with 1 to 5 identical or different halogen atoms, such as fluorine and chlorine atoms, C₁-C₄-alkylsulfinyl, C₁-C₄-haloalkylsul finyl with 1 to 5 identical or different halogen atoms, such as fluorine and chlorine atoms, C₁-C₄-alkylsulfonyl, C₁-C₄-haloalkylsulfonyl with 1 up to 5 identical or different halogen atoms, such as fluorine and chlorine atoms or for thiocarbamoyl.

R³ preferably represents hydrogen-C₁-C₄-alkyl, C₁-C₄-haloalkyl with 1 to 5 identical or different halogen atoms, such as fluorine and chlorine atoms, C₁-C₄-alkoxy-C₁-C₄-alkyl, C₁-C₄-alkyl-carbonyl, C₁-C₄-alkyl sulfonyl, each optionally up to three times, the same or different the phenylcarbonyl, phenylsulfonyl or substituted in the phenyl ring Benzyl, each of which is halogen, nitro, cyano, C₁-C₄- Alkyl, C₁-C₂-haloalkyl with 1 to 5 identical or different halo gene atoms, such as fluorine and chlorine atoms, C₁-C₄-alkoxy, C₁-C₄-alkylthio, C₁-C₂-haloalkoxy with 1 to 5 identical or different halogen atoms, such as fluorine and chlorine atoms or C₁-C₂-haloalkylthio with 1 to 5 identical or different halogen atoms, such as fluorine and chlorine atoms come into question, or for single to triple, the same or, if necessary differently substituted by C₁-C₄-alkyl or halogen C₃-C₆-cyclo alkyl.

R⁴ preferably represents optionally up to triple, the same or variously substituted phenyl, the substituents being halogen, nitro, Cyano, C₁-C₁₂-alkyl, C₁-C₁₂-haloalkyl with 1 to 5 identical or  various halogen atoms, such as fluorine and chlorine atoms, C₁-C₁₂ alkoxy, C₁-C₁₂ haloalkoxy with 1 to 5 identical or different halogen atoms, such as fluorine and chlorine atoms, C₁-C₁₂-alkylthio, C₁-C₁₂-halogenal kylthio with 1 to 5 identical or different halogen atoms, such as fluorine and chlorine atoms, C₂-C₁₂-alkenyl, C₂-C₁₂-haloalkenyl with 1 to 5 same or different halogen atoms, such as fluorine and chlorine atoms, optionally single to triple, identical or different by C₁-C₄- Alkyl or halogen substituted C₃-C₈-cycloalkyl as well as given if necessary, single to triple, identical or different by halogen, nitro, Cyano, C₁-C₄-alkyl, C₁-C₄-haloalkyl with 1 to 5 identical or ver different halogen atoms, such as fluorine and chlorine atoms, C₁-C₄-alkoxy, C₁- C₄-haloalkoxy with 1 to 5 identical or different halogen atoms, such as fluorine and chlorine atoms, C₁-C₄-alkylthio, C₁-C₄-haloalkylthio with 1 up to 5 identical or different halogen atoms, such as fluorine and chlorine atoms, C₁-C₄-alkylthio-C₁-C₄-alkyl, C₁-C₄-alkylsulfonyl, C₁-C₄-halogen alkylsulfonyl with 1 to 5 identical or different halogen atoms, such as Fluorine and chlorine atoms, C₁-C₄-alkyl-carbonyl, C₁-C₄-alkoxy-carbonyl, Thioamide, C₁-C₄-alkoximino-C₁-C₄-alkyl or optionally by C₁-C₄-alkyl substituted oxdiazolyl substituted phenyl, phenoxy, phenyl thio, benzyl or benzyloxy are possible, or for each optionally single to triple, the same or ver differently substituted C₃-C₈-cycloalkyl or C₅-C₈-cycloalkenyl, wherein as substituents C₁-C₄-alkyl, C₁-C₄-haloalkyl with 1 to 5 of the same or various halogen atoms, such as fluorine and chlorine atoms, C₁-C₄- Alkoxy, C₁-C₄ haloalkoxy with 1 to 5 identical or different Halogen atoms, such as fluorine and chlorine atoms, C₃-C₈-cycloalkyl, and ge possibly up to three times, the same or different by halogen, Cyano, nitro, C₁-C₄-alkyl, C₁-C₄-haloalkyl with 1 to 5 identical or various halogen atoms, such as fluorine and chlorine atoms, C₁-C₄ alkoxy or C₁-C₄ haloalkoxy with 1 to 5 identical or different halo genomic, such as fluorine and chlorine atoms substituted phenyl in question come.

Y preferably represents C₁-C₆-alkylene, C₁-C₆-hydroxyalkylene, C₁-C₄-alkoxy- C₁-C₆-alkylene, C₁-C₄-alkylcarbonyloxy-C₁-C₆-alkylene, cyano-C₁-C₆-alky len, C₁-C₄ haloalkylene with 1 to 5 identical or different halo gene atoms such as fluorine and chlorine atoms; possibly up to three  times, identical or differently substituted by fluorine, chlorine or methyl C₃-C₆-cycloalkyl-C₁-C₄-alkylene, C₂-C₄-alkenylene or C₁-C₄-alkyleneoxy.

R¹ particularly preferably represents methyl, ethyl, n- or i-propyl) n-, i-, s- or t-butyl; CH₂F, CHF₂, CF₃, CH₂Cl, CH₂Br, CHClCH₃; Methoxy, ethoxy, Methoxymethyl, ethoxymethyl; Methylthiomethyl or cyclopropyl.

R² particularly preferably represents hydrogen, chlorine, bromine, cyano, nitro, Thiocyanato; Methoxycarbonyl, ethoxycarbonyl, i-propoxycarbonyl, n- Propoxycarbonyl; Allyloxycarbonyl; SCF₃, SCCl₂F, SOCF₃, SOCCl₂F, SO₂CF₃, SO₂CCl₂F, SCHF₂, SOCHF₂, SO₂CHF₂ or CSNH₂.

R³ particularly preferably represents hydrogen, methyl, ethyl, n- or i-propyl; Methoxymethyl, ethoxymethyl, n-propoxymethyl, n-butoxymethyl; Methyl carbonyl, methylsulfonyl; in each case, if necessary, single or double, identical or different by fluorine, chlorine, methyl or trifluoromethyl substituted phenylcarbonyl or benzyl; or cyclopropyl.

R⁴ particularly preferably represents the same, if appropriate single to triple or differently substituted phenyl, halogen being the substituent, Nitro, cyano, C₁-C₁₂-alkyl, C₁-C₁₂-haloalkyl with 1 to 5 identical or various halogen atoms, such as fluorine and chlorine atoms, C₁-C₄ alkoxy, C₁-C₄ haloalkoxy with 1 to 5 identical or different halogen atoms, such as fluorine and chlorine atoms, C₁-C₄-alkylthio, C₁-C₄-haloalkyl thio with 1 to 5 identical or different halogen atoms, such as fluorine and chlorine atoms, C₂-C₄-alkenyl, C₂-C₄-haloalkenyl with 1 to 5 glei Chen or different halogen atoms, such as fluorine and chlorine atoms and each through single to triple, the same or different Halogen, nitro, cyano, C₁-C₄-alkyl, C₁-C₄-haloalkyl with 1 to 5 glei Chen or different halogen atoms, such as fluorine and chlorine atoms, C₁- C₄-alkoxy, C₁-C₄-haloalkoxy with 1 to 5 identical or different Halogen atoms, such as fluorine and chlorine atoms, C₁-C₄-alkylthio, C₁-C₄-halo genalkylthio with 1 to 5 identical or different halogen atoms, such as Fluorine or chlorine atoms, C₁-C₄-alkylthio-C₁-C₄-alkyl, C₁-C₄-alkylsulfonyl, C₁-C₄ haloalkylsulfonyl with 1 to 5 identical or different halo gene atoms, such as fluorine or chlorine atoms, C₁-C-alkyl-carbonyl, C₁-C₄-alk oxy-carbonyl, thioamide, C₁-C₄-alkoximino-C₁-C₂-alkyl or given  if substituted by C₁-C₂-alkyl substituted 1,2,4-oxdiazolyl-3-yl Phenoxy, phenylthio or benzyloxy come into question.

Y is particularly preferably one of the groups

R¹ very particularly preferably represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl; CH₂F, CHF₂, CF₃, CH₂Cl, CH₂Br, methoxy or ethoxy.
R² very particularly preferably represents hydrogen, chlorine, bromine, cyano, nitro, thiocyanato, methoxycarbonyl or ethoxycarbonyl.
R³ very particularly preferably represents hydrogen, methyl, ethyl, methoxy methyl, ethoxymethyl, methylcarbonyl, phenylcarbonyl or methylsulfonyl.
R⁴ very particularly preferably represents phenyl which is monosubstituted to trisubstituted by identical or different substituents, the substituents being fluorine, chlorine, bromine, nitro, cyano, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl; Methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy; Methylthio, CF₃, OCF₃, OCHF₂, SCF₃, SCCl₂F; CH₂Br, CH₂Cl and ge optionally single to triple, identical or different by fluorine, chlorine, bromine, nitro, cyano, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, Ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methylthio, methylthiomethyl, CF₃, OCF₃, OCHF₂, SCF₃, SCCl₂F, CH₂Br, CH₂Cl, acetyl, ethylcarbonyl, methoxycarbonyl, methylsulfonyl, trifluoromethylsulfonyl , Thioamide, methoximinomethyl, 1- (methoximino) ethyl, 1- (ethoximino) ethyl, 1,2,4-oxdiazol-3-yl or 5-methyl-1,2,4-oxdiazol-3-yl substituted phenoxy come
Y very particularly preferably represents -CH₂- or -CH (CH₃) -.

Preferred compounds according to the invention are substances of the formulas (IA) or (IB):

in which
R¹, R² and R³ stand for the abovementioned general, preferred, particularly preferred and very particularly preferred meanings and
X¹, X², X³, X⁴ and X⁵ stand for the substituents mentioned above under R⁴ in general, preferably, particularly preferably and very particularly preferably for the phenyl or phenoxy radical and
X¹, X², X³ and X⁴ can also each represent hydrogen.

Another preferred group of compounds are those of the formulas (IA) or (IB) in which the phenoxy radical para to the NR³-CS-CH₂- or NR³-CS-CH (CH₃) group stands, among these compounds those particularly are preferred in which the substituents X¹, X², X³ and X⁴ for hydrogen stand.

The radicals listed above or listed in preferred areas definitions and explanations apply to the end products and to the initial and intermediates accordingly. These residual definitions can be found under each other, so also between the respective preferred areas, any combination be kidneyed.  

According to the invention, preference is given to the compounds of the formula (I) in which a combination of those listed as preferred (preferred) above Meanings exist.

According to the invention, particular preference is given to the compounds of the formula (I), in which are a combination of those listed as particularly preferred above Meanings exist.

The compounds of the formula are very particularly preferred according to the invention (I) in which a combination of the above is particularly preferred listed meanings is present.

In the residue definitions listed above and below are hydrocarbons residues such as alkyl or alkenyl - also in combination with heteroatoms such as Alkoxy or alkylthio - if possible straight or branched.

In addition to the preparation examples, the following compounds are detailed of the formula (IC):

Table A

For example, 5-amino-4-chloro-3-ethyliso is used according to process (Aa) thiazole and 4- (4-cyanophenoxy) phenylthioacetic acid chloride as starting materials, the course of the process according to the invention can be followed by the following reac are reproduced:

For example, 5-amino-4-chloro-3-ethyliso is used according to process (Ab) thiazole and 4- (4-chlorophenoxy) -phenyl-dithioacetic acid methyl ester as starting substances, the course of the process according to the invention can be determined by the following Reaction scheme are reproduced:

Is used according to method (B), for example N- (4-Chloro-3-ethyl-5-thiazolyl) -4- (4-cyanophenoxy) phenylacetic acid amid as raw material and Lawes sons reagent (2,4-bis- (4-methoxyphenyl) -1,3-dithia-2,4-diphosphetane-2,4-disulfide) - as a sulfurizing agent, the course of the process according to the invention are represented by the following reaction scheme:

The to carry out the processes (Aa) and (Ab) according to the invention as N- (5-isothiazolyl) amides of the formula (II) required as starting materials are wide known (see the patent applications cited at the beginning).

The ver as starting materials in process (Aa) according to the invention Compounds of formula (III) are generally known compounds of organic chemistry. In formula (III) G is preferably imidazolyl (see, e.g., Liebigs Ann. Chem. 739, 201 (1970).

The also to carry out the method according to the invention (Ab) as off Formula (IV) provides a general definition of the dithioesters required. In this formula (IV) Alk is preferably methyl or CH₂COONa.

The dithioesters of the formula (IV) are known (cf. e.g. Tetrahedron 2663 (1984), J. Chem. Research (M) 2701 (1988), Chem. Ind. (London) 803, 1974; Soot. Chem. Rev. 45, 1035 (1976)) and / or can be according to known, analog Ver manufacture driving.

The compounds of the formula required for carrying out process (B) (V) are known from the patent applications cited at the beginning.

The sulfurizing agents used in carrying out the invention Process (B) preferably phosphorus pentasulfide or Lawesson's reagent [2,4- Bis (4-methoxyphenyl) -1,3,2,4-dithiadiphosphetane-2,4-dithione] (see also Tetralie dron Vol. 41, No. 22, 5061 ff (1985)) in question.  

The process (Aa) described above for the preparation of the compounds of For mel (I) is carried out in the presence of a diluent. As a thinner All common solvents can be used.

Halogenated aliphatic or aro are preferably usable Matic hydrocarbons, ethers or nitriles such as. B. cyclohexane, toluene, Chlorobenzene, chloroform, dichloromethane, dichloroethane, dioxane, tetrahydrofuran, Diethyl ether or acetonitrile.

The process (Aa) described above for the preparation of the compounds of Formula (I) is carried out in the presence of a base (cf. also Chem. Ber. 98, 829 (1965); Liebigs Ann. Chem. 739, 201 (1970) and 636 (1973).

All conventional proton acceptors can be used as bases in process (Aa) be set. Alkali or alkaline earth metal hydroxides are preferably usable, Alkali or alkaline earth carbonates or bicarbonates or nitrogen bases. Ge Examples include sodium hydroxide, calcium hydroxide, potassium carbonate, Sodium hydrogen carbonate, triethylamine, dibenzylamine, diisopropylamine, pyridine, Quinoline, diazabicyclooctane (DABCO), diazabicyclonones (DBN) and diazabi cycloundecene (DBU).

The reaction temperatures in process (Aa) described in can be varied over a wide range. Generally one works at Tempe temperatures between -40 ° C and + 200 ° C, preferably between 0 ° C and 100 ° C.

When carrying out the process (Aa) described above for producing the Compounds of formula (1) are generally used per mole of 5-aminoisothiazole of formula (II) 1 to 2 moles, preferably 1 to 1.5 moles of the compound Formula (III).

In some cases, it proves to be advantageous to use the 5-aminoisothiazoles of the formula (II) in the form of their hydrohalides, in particular as hydro use chloride.

The end products are worked up and isolated in a generally known manner and way.  

Suitable diluents for carrying out the inventive Process (Ab) all usual solvents in question. Preferably usable are optionally halogenated aliphatic or aromatic hydrocarbons, such as methylene chloride, dichloroethane, cyclohexane, toluene or chlorobenzene.

However, it is also possible to work in bulk without a solvent.

The reaction temperatures can be carried out when carrying out the process according to the invention Process (Ab) can be varied over a wide range. Generally ar one works at temperatures between 0 ° C and 150 ° C, preferably between 20 ° C and 120 ° C.

When carrying out the process (Ab) according to the invention, the reaction is carried out per mole Pyridylamine of the formula (III) in general 1 to 3 mol, preferably 1 to 1.5 Mol dithioester of formula (IV). The processing and isolation takes place after usual methods.

Suitable diluents for carrying out the inventive Process (B) preferably hydrocarbons, such as toluene, xylene, tetralin, Hexane or cyclohexane in question.

The reaction temperatures can be carried out when carrying out the process according to the invention Process (B) can be varied over a wide range. Generally works one at temperatures between 0 ° C and 200 ° C, preferably between 20 ° C and 150 ° C.

When carrying out process (A) according to the invention, the reaction is carried out per mole Compound of formula (II) generally between 1 and 3 moles, preferably between 1 and 2 moles of sulfurizing agent. The processing takes place according to übli methods.

The compounds of formula (I) can also be obtained by 5-iso thiazolyl isothiocyanates of the formula (VI)

in which
R¹ and R² have the meaning given above,
with Grignard compounds of the formula (VII)

Hal′-Mg-Y-R⁴ (VII)

in which
Hal 'represents halogen (especially chlorine or bromine) and
Y and R⁴ have the meaning given above,
implemented in the usual way (see also JACS 4849 (1955)).

The N- (5-isothiazolyl) thioamides of the formula (Iα)

in which
R¹, R², R³ and A have the meaning given above,
can also be obtained by using pyridylamines of the formula (III)

in which
R¹, R² and R³ have the meaning given above,
with carbonyl compounds of formula (VIII)

E-CO-CH₂-A (VIII)

in which
E represents hydrogen or methyl and
A has the meaning given above,
in the presence of sulfur (see also Pet. Chem. USSR (Engl. Transl.) 345 (1993)).

The substituted N- (5-isothiazolyl) thioamides of the formula (I) according to the invention can optionally be converted into their corresponding N- in a known manner. Oxide or salt derivatives are transferred and these are also the subject of the present application.

The active ingredients are suitable for good plant tolerance and inexpensive warmth blood toxicity to control animal pests, especially insects, Arachnids and nematodes found in agriculture, in forests, in and material protection as well as in the hygiene sector. You can before are preferably used as pesticides. You are against normal sen sible and resistant species as well as against all or individual stages of development effective. The pests mentioned above include:  

From the order of the Isopoda z. B. Oniscus asellus, Armadillidium vulgare, Por cellio scaber.

From the order of the Diplopoda z. B. Blaniulus guttulatus.

From the order of the Chilopoda z. B. Geophilus carpophagus, Scutigera spec.

From the order of the Symphyla z. B. Scutigerella immaculata.

From the order of the Thysanura z. B. Lepisma saccharina.

From the order of the Collembola z. B. Onychiums armatus.

From the order of Orthoptera z. B. Blatta orientalis, Periplaneta americana, Leucophaea maderae, Blattella germanica, Acheta domesticus, Gryllotalpa spp., Locusta migratoria migratorioides, Melanoplus differentialis, Schistocerca gregaria.

From the order of the Dermaptera z. B. Fofflcula auricularia.

From the order of the Isoptera z. B. Reticulitermes spp.

From the order of the Anoplura z. B. Pediculus humanus corporis, Haematopinus spp., Linognathus spp.

From the order of the Mallophaga z. B. Trichodectes spp., Damalinea spp.

From the order of the Thysanoptera z. B. Hercinothrips femoralis, Thrips tabaci.

From the order of Heteroptera z. B. Eurygaster spp., Dysdercus intermedius, Piesma quadrata, Cimex lectularius, Rhodnius prolixus, Triatoma spp.

From the order of Homoptera z. B. Aleurodes brassicae, Bemisia tabaci, Trialeurodes vaporariorum, Aphis gossypii, Brevicoryne brassicae, Cryptomyzus ribis, Aphis fabae, Aphis pomi, Eriosoma lanigerum, Hyalopterus arundinis, Phylloxera vastatrix, Pemphigus spp., Macrosiphum avenae, Myzus spp., Phorodon humuli, Rhopalosiphum padi, Empoasca spp., Euscelis bilobatus, Nephotettix  cincticeps, Lecanium corni, Saissetia oleae, Laodelphax striatellus, Nilaparvata lugens, Aonidiella aurantii, Aspidiotus hederae, Pseudococcus spp., Psylla spp.

From the order of the Lepidoptera z. B. Pectinophora gossypiella, Bupalus piniarius, Cheimatobia brumata, Lithocolletis blancardella, Hyponomeuta padella, Plutella maculipenni s, Malacosoma neustri a, Euprocti s chry sorrhoea, Lymantri a spp., Bucculatrix thurberiella, Phyllocnistis citrella, Agrotis spp., Euxoa spp., Feltia spp., Earias insulana, Heliothis spp., Spodoptera exigua, Mamestra brassicae, Panolis flammea, Spodoptera litura, Spodoptera spp., Trichoplusia ni, Carpocapsa pomonella, Pieris spp., Chilo spp., Pyrausta nubilalis, Ephestia kuehniella, Galleria mellonella, Tineola bisselliella, Tinea pellionella, Hofmannophila pseudospretella, Cacoecia podana, Capua reticulana, Choristoneura fumiferana, Clysia ambiguella, Homona magnanima, Tortrix viridana.

From the order of the Coleoptera z. B. Anobium punctatum, Rhizopertha dominica, Bruchidius obtectus, Acanthoscelides obtectus, Hylotrupes bajulus, Agelastica alni, Leptinotarsa decemlineata, Phaedon cochleariae, Diabrotica spp., Psylliodes chrysocephala, Epilachna varivestis, Atomaria spp., Oryzaephilus surinamensis, Anthonomus spp., Sitophilus spp., Otiorrhynchus sulcatus, Cosmopolites sordidus, Ceuthorrhynchus assimilis, Hypera postica, Dermestes spp., Trogoderma spp., Ahthrenus spp., Attagenus spp., Lyctus spp., Meligethes aeneus, Ptinus spp., Niptus hololeucus, Gibbium psylloides, Tribolium spp., Tenebrio molitor, Agriotes spp., Conoderus spp., Melolontha melolontha, Amphimallon solstitialis, Costelytra zealandica.

From the order of the Hymenoptera z. B. Diprion spp., Hoplocampa spp., Lasius spp., Monomorium pharaonis, Vespa spp.

From the order of the Diptera z. B. 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.

From the order of the Siphonaptera z. B. Xenopsylla cheopis, Ceratophyllus spp.  

From the order of the Arachnida z. B. Scorpio maurus, Latrodectus mactans.

From the order of Acarina z. B. 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.

The plant parasitic nematodes include z. B. Pratylenchus spp., Radopho lus 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 noteworthy with a high level of insecticidal and acaricidal activity.

They can be used with particularly good success to combat plant damage insects, such as against the horseradish beetle larvae (Phae don cochlaeriae), the caterpillars of the cockroach (Plutella maculipennis), the green one Rice leafhopper (Nephotettix cinctriceps) and the caterpillars of the owl butterfly (Spodoptera frugiperda) or to control plant-damaging mites, such as for example against the common spider mite (Tetranychus urticae).

The active ingredients can be converted into the usual formulations, such as Lö solutions, emulsions, wettable powders, suspensions, powders, dusts, pastes, sol Liche powders, granules, suspension emulsion concentrates, impregnated with active ingredients natural and synthetic substances as well as very fine encapsulations in polymeric substances fen.

These formulations are prepared in a known manner, e.g. B. by Vermi the active ingredients with extenders, i.e. liquid solvents and / or solid carriers, optionally using surface-active agents Agents, that is emulsifiers and / or dispersants and / or foam generators resources.

In the case of the use of water as an extender, e.g. B. also organic Solvents are used as auxiliary solvents. As a liquid solvent  essentially come into question: aromatics, such as xylene, toluene, or alkylnaph thalines, chlorinated aromatics and chlorinated aliphatic hydrocarbons, such as Chlorobenzenes, chlorethylenes or methylene chloride, aliphatic hydrocarbons substances such as cyclohexane or paraffins, e.g. B. 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.  

The following are suitable as solid carriers:
e.g. B. ammonium salts and natural rock powders such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and synthetic rock powders, such as highly disperse silica, aluminum oxide and silicates, as solid carriers for granules are possible: z. B. broken and fractionated natural rocks such as calcite, marble, pumice, sepiolite, dolomite and synthetic granules from inorganic and organic flours as well as granules from organic material such as sawdust, coconut shells, corn cobs and tobacco stems; as emulsifying and / or foam-generating agents come into question: z. B. nonionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, e.g. B. alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates and protein hydrolyzates; as dispersing agents come into question: z. B. lignin sulfite and methyl cellulose.

Adhesives such as carboxymethyl cellulose, natural, can be used in the formulations Liche and synthetic powdery, granular or latex-shaped polymers used such as gum arabic, polyvinyl alcohol, polyvinyl acetate, and natural Phospholipids such as cephalins and lecithins and synthetic phospholipids. Other additives can be mineral and vegetable oils.

Dyes such as inorganic pigments, e.g. B. iron oxide, titanium oxide, Ferrocyan blue and organic dyes such as alizarin, azo and metal phthalalo cyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, Cobalt, molybdenum and zinc can be used.

The formulations generally contain between 0.1 and 95% by weight Active ingredient, preferably between 0.5 and 90%.

The active ingredient according to the invention can be in its commercially available formulations as well as in the application forms prepared from these formulations in Mi with other active ingredients, such as insecticides, attractants, sterilants, Bak tericides, acaricides, nematicides, fungicides, growth regulators or herbicides. Insecticides include, for example, phosphorus acid esters, carbamates, carboxylic acid esters, chlorinated hydrocarbons, phenyl ureas, substances produced by microorganisms u. a.  

Particularly cheap mixing partners are e.g. B. the following:

Fungicides

2-aminobutane; 2-anilino-4-methyl-6-cydopropyl-pyrimidine; 2 ′, 6′-dibromo-2-methyl-4′-trifluoromethoxy-4′-trifluoromethyl-1,3-thiazole-5-carboxanide; 2,6-di-chloro-N- (4-trifluoromethylbenzyl) benzamide; (E) -2-methoxyimino-N-methyl-2- (2-phenoxyphenyl) acetamide; 8-hydroxyquinoline sulfate; Methyl- (E) -2- {2- [6- (2-cyano-phenoxy) pyrimidin-4-yloxy] phenyl} -3-methoxyacrylate; Methyl (E) methoximino [alpha- (o-tolyloxy) -o-tolyl] acetate; 2-phenylphenol (OPP), aldimorph, ampropylfos, anilazine, azaconazole,
Benalaxyl, Benodanil, Benomyl, Binapacryl, Biphenyl, Bitertanol, Blasticidin-S, Bromuconazole, Bupirimate, Buthiobate,
Calcium polysulfide, captafol, captan, carbendazim, carboxin, quinomethionate (quinomethionate), chloroneb, chloropicrin, chlorothalonil, chlozolinate, cufraneb, cymoxanil, cyproconazole, cyprofuram,
Dichlorophene, diclobutrazole, diclofluanid, dic1omezin, dicloran, diethofencarb, difenoconazole, dimethirimol, dimethomorph, diniconazole, dinocap, diphenylamine, dipyrithione, ditalimfos, dithianon, dodine, drazoxolone,
Edifenphos, epoxyconazole, ethirimol, etridiazole,
Fenarimol, Fenbuconazole, Fenfuram, Fenitropan, Fenpiclonil, Fenpropidin, Fen propimorph, Fentinacetat, Fentinhydroxyd, Ferbam, Ferimzone, Fluazinam, Fludi oxonil, Fluoromide, Fluquinconazole, Flusilazole, Flusulfamide, Flutolanil, Fulinolide, Flu triafolide , Furalaxyl, Furmecyclox,
Guazatine,
Hexachlorobenzene, hexaconazole, hymexazole,
Imazalil, Imibenconazol, Iminoctadin, Iprobefos (IBP), Iprodione, Isoprothiolan,
Kasugamycin, copper preparations such as: copper hydroxide, copper naphthenate, copper oxychloride, copper sulfate, copper oxide, oxine copper and Bordeaux mixture,
Mancopper, Mancozeb, Maneb, Mepanipyrim, Mepronil, Metalaxyl, Metconazol, Methasulfocarb, Methfuroxam, Metiram, Metsulfovax, Myclobutanil,
Nickel dimethyldithiocarbamate, nitrothal isopropyl, Nuarimol,
Ofurace, oxadixyl, oxamocarb, oxycarboxin,
Pefurazoat, Penconazol, Pencycuron, Phosdiphen, Phthalid, Pimaricin, Piperalin, Polycarbamate, Polyoxin, Prob enazol, Prochloraz, Procymidon, Propamocarb, Propiconazole, Propineb, Pyrazophos, Pyrifenox, Pyrimethanil, Pyroquilon,
Quintozen (PCNB),
Sulfur and sulfur preparations,
Tebuconazole, Tecloftalam, Tecnazen, Tetraconazole, Thiabendazole, Thicyofen, Thiophanat-methyl, Thiram, Tolclophos-methyl, Tolylfluanid, Triadimefon, Triadi menol, Triazoxid, Trichlamid, Tricyclazol, Tridemorph, Triforazol, Tri,
Validamycin A, vinclozolin,
Zineb, ziram.

Bactericides

Bronopol, dichlorophene, nitrapyrin, nickel dimethyldithiocarbamate, Kasugamy cin, octhilinone, furan carboxylic acid, oxytetracycline, probenazole, streptomycin, Tec loftalam, copper sulfate and other copper preparations.

Insecticides / acaricides / nematicides

Abamectin, AC 303 630, Acephat, Acrinathrin, Alanycarb, Aldicarb, Alpha methrin, Amitraz, Avermectin, AZ 60541, Azadirachtin, Azinphos A, Azinphos M, Azocyclotin,
Bacillus thuringiensis, Bendiocarb, Benfuracarb, Bensultap, Betacyfluthrin, Bifen thrin, BPMC, Brofenprox, Bromophos A, Bufencarb, Buprofezin, Butocarboxin, Butylpyridaben,
Cadusafos, Carbaryl, Carbofuran, Carbophenothion, Carbosulfan, Cartap, CGA 157 419, CGA 184699, Chloethocarb, Chlorethoxyfos, Chlorfenvinphos, Chlorflu azuron, Chlormephos, Chlorpyrifos, Chlorpyrifos M, Cis-Resmethrin, Clocythrinhrhrhrinhrhrinhrinhrinhrinhrinhrinhrinhrinhrinhrinhrinhrinhrofhrinhrinhrinhrinhrinhrinhrofhrinothrinothrinhrhrinhrhrinhrinhrinhrofhrinothrinothrinothrinhrhrinhrhrinhrinhrofhrinothrinothrinothrinophrinothrinophrinothrinophrinothrinophrinophrine , Cyhexatin, cypermethrin, cyromazine,
Deltamethrin, Demeton M, Demeton S, Demeton-S-methyl, Diafenthiuron, Diazinon, Dichlofenthion, Dichlorvos, Dicliphos, Dicrotophos, Diethion, Diflu benzuron, Dimethoat, Dimethylvinphos, Dioxathion, Disulfoton,
Edifenphos, Emamectin, Esfenvalerat, Ethiofencarb, Ethion, Ethofenprox, Etho prophos, Etrimphos,
Fenamiphos, Fenazaquin, Fenbutatinoxid, Fenitrothion, Fenobucarb, Fenothiocarb, Fenoxycarb, Fenpropathrin, Fenpyrad, Fenpyroximat, Fenthion, Fenvalerate, Fipro nil, Fluazinam, Flucycloxuron, Flucythrinat, Flufenoxuron, Fufionatexfonophon, Fufionproxophon, Fufonproxophone, Fufonproxophon, Fufonproxophon, Fufonfox, Fufionfox, Fufionfox, Fufone
HCH, heptenophos, hexaflumuron, hexythiazox,
Imidacloprid, Iprobefos, Isazophos, Isofenphos, Isoprocarb, Isoxathion, Iver mectin, Lambda-cyhalothrin, Lufenuron,
Malathion, Mecarbam, Mervinphos, Mesulfenphos, Metaldehyde, Methacrifos, Methamidophos, Methidathion, Methiocarb, Methomyl, Metolcarb, Milbemectin, Monocrotophos, Moxidectin,
Naled, NC 184, M 25, Nitenpyram,
Omethoate, Oxamyl, Oxydemethon M, Oxydeprofos,
Parathion A, Parathion M, Permethrin, Phenthoat, Phorat, Phosalon, Phosmet, Phosphamidon, Phoxim, Pirimicarb, Pirimiphos M, Pirimiphos A, Profenofos, Promecarb, Propaphos, Propoxur, Prothiofos, Prothoat, Pymetrozin, Pyrachlophhine, Pyrachlophhion, Pyrachlophion, Pyrachlophin, Pyrachlophin, Pyrachlophin, Pyrachlophin, Pyrachlophin, Pyrachlophin, Pyrachlophion Pyridaben, pyrimidifen, pyriproxifen,
Quinalphos,
RH 5992,
Salithion, Sebufos, Silafluofen, Sulfotep, Sulprofos,
Tebufenozid, Tebufenpyrad, Tebupirimphos, Teflubenzuron, Tefluthrin, Temephos, Terbam, Terbufos, Tetrachlorvinphos, Thiafenox, Thiodicarb, Thiofanox, Thio methon, Thionazin, Thuringiensin, Tralomichonon, Triaromenontron, Triaromenontron, Triarathenlarbon, Triarathenltronium, Triarathenltronium, Triarathenltronium, Triarathenltronium, Triarathenltronium, Triarathenltronium, Triaromenontrin, Triarathenltronium, Triaromenontrin, Triarathenltron, Triaromenontron
Vamidothione, XMC, xylylcarb, YI 5301/5302, zetamethrin.

A mixture with other known active ingredients, such as herbicides or with Fertilizers and growth regulators are possible.

The active compounds according to the invention can also be used in their commercially available form formulations and in the application forms prepared from these formulations in a mixture with synergists. Synergists are connections through which the effect of the active ingredients is increased without the added synergist must be actively active itself.

The active ingredient content of the prepared from the commercially available formulations Application forms can vary widely. The drug concentration the use forms can be from 0.0000001 to 95% by weight of active ingredient, preferably between 0.0001 and 1% by weight.

The application takes place in a customary manner adapted to the application forms Wise.

When used against hygiene and storage pests, the stands out Active ingredient through an excellent residual effect on wood and clay as well due to 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, hair lice, Featherlings and fleas. These parasites include:
From the order of the Anoplurida z. B. Haematopinus spp., Linognathus spp., Pediculus spp., Phtirus spp., Solenopotes spp.

From the order of the Mallophagida and the subordinates Amblycerina as well Ischnocerina e.g. B. Trimenopon spp., Menopon spp., Trinoton spp., Bovicola spp., Werneckiella spp., Lepikentron spp., Damalina spp., Trichodectes spp., Felicola spp.

From the order Diptera and the subordinates Nematocerina as well Brachycerina e.g. B. 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 spp., Philipomyia spp., Braula spp., Musca spp., Hydrotaea spp., Stomoxys spp., Haematobia spp., Morellia spp., Fannia spp., Glossina spp., Calliphora spp., Lucilia spp., Chrysomyia spp., Wohlfahrtia spp., Sarcophaga spp., Oestms spp., Hypoderma spp., Gasterophilus spp., Hippobosca spp., Lipoptena spp., Melophagus spp.

From the order of the Siphonapterida z. B. Pulex spp., Ctenocephalides spp., Xenopsylla spp., Ceratophyllus spp.

From the order of the Heteropterida z. B. Cimex spp., Triatoma spp., Rhodnius spp., Panstrongylus spp.

From the order of the Blattarida z. B. Blatta orientalis, Periplaneta americana, Blattela germanica, Supella spp.

From the subclass of Acaria (Acarida) and the orders of the Meta and Mesostigmata e.g. B. Argas spp., Ornithodorus spp., Otobius spp., Ixodes spp., Amblyomma spp., Boophilus spp., Dermacentor spp., Haemophysalis spp., Hyalomma spp., Rhipicephalus spp., Dermanyssus spp., Raillietia spp., Pneumo nyssus spp., Sternostoma spp., Varroa spp.  

From the order of the Actinedida (Prostigmata) and Acaridida (Astigmata) z. B. Acarapis spp., Cheyletiella spp., Ornithocheyletia spp., Myobia spp., Psorergates spp., Demodex spp., Trombicula spp., Listrophorus spp., Acarus spp., Tyrophagus spp., Caloglyphus spp., Hypodectes spp., Pterolichus spp., Psoroptes spp., Chorioptes spp., Otodectes spp., Sarcoptes spp., Notoedres spp., Knemidocoptes spp., Cytodites spp., Laminosioptes spp.

The active compounds of the formula (I) according to the invention are also suitable for loading fighting arthropods that farm livestock, such as B. cattle, Sheep, goats, horses, pigs, donkeys, camels, buffaloes, rabbits, chickens, Turkeys, ducks, geese, bees, other pets such as B. Dogs, cats, parlors birds, aquarium fish and so-called experimental animals, such as B. hamster, sea pigs, rats and mice. By fighting this arthro deaths and reduced performance (for meat, milk, wool, Hides, eggs, honey, etc.) can be reduced, so that by using the Active ingredients according to the invention a more economical and easier animal husbandry is possible.

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, Tab Latvian, capsules, watering, drenching, granules, pastes, boluses, feed-through Method, of suppositories, by parenteral administration, such as by injections (intramuscular, subcutaneous, intravenous, intraperitoneal, etc.), Implan tate, by nasal application, by dermal application in the form, for example of diving or bathing (dipping), spraying (spray), pouring on (pour-on and Spot-on), washing, powdering and with the help of active ingredients Shaped bodies, such as collars, ear tags, tail tags, limb straps, Halters, marking devices etc.

When used for cattle, poultry, pets etc. you can use the active ingredients of the formula (I) as formulations (for example powders, emulsions, flowable Agents), which contain the active ingredients in an amount of 1 to 80 wt .-%, directly or after 100 to 10,000-fold dilution, or as a chemical Use bath.

It was also found that the compounds of the invention have a high Show insecticidal activity against insects that destroy technical materials.  

The following are examples and preferably - but without limitation - Called insects:

Beetle like
Hylotrupes bajulus, Chlorophorus pilosis, Anobium punctatum, Xestobium rufovillosum, Ptilinus pecticornis, Dendrobium pertinex, Ernobius mollis, Priobium carpini, Lyctus brunneus, Lyctus africanus, Lyctus planicollis, Lyctus linearesces, Lyctus pubis linearis, Lyctus pubis linearis, speculum Tryptodendron spec. Apate monachus, Bostrychus capucins, Heterobostrychus brunneus, Sinoxylon spec. Dinoderus minutus.

Skin wings like
Sirex juvencus, Urocerus gigas, Urocerus gigas taignus, Urocerus augur.

Termites like
Kalotermes flavicollis, Cryptotermes brevis, Heterotermes indicola, Reticulitermes fl avip es, Reti culitermes santonensi s, Reti culitermes lucifugus, Mastotermes darwiniensis, Zootermopsis nevadensis, Coptotermes formosanus.

Bristle tails like
Lepisma saccharina.

In the present context, technical materials include non-living ones Understand materials, such as preferably plastics, adhesives, glues, paper and cartons, leather, wood and wood processing products and paints.

It is very particularly preferred to protect against insect attack material around wood and wood processing products.

Among wood and wood processing products, which by the invention Agents or mixtures containing them can be protected is exemplary to understand: timber, wooden beams, railway sleepers, bridge parts, jetties, Wooden vehicles, boxes, pallets, containers, telephone poles, wooden panels, Wooden windows and doors, plywood, chipboard, carpentry or wood pro products that are used in general in house construction or in joinery Find.  

The active ingredients can be used as such, in the form of concentrates or in general usual formulations such as powders, granules, solutions, suspensions, emul sions or pastes.

The formulations mentioned can be prepared in a manner known per se be, e.g. B. by mixing the active ingredients with at least one solution or diluent, emulsifier, dispersing and / or binding or fixing agent tels, water repellants, possibly desiccants and UV stabilizers and opp if necessary dyes and pigments and other processing aids.

The insecticidal agents used to protect wood and wood-based materials or concentrates contain the active ingredient according to the invention in a concentra tration from 0.0001 to 95 wt .-%, in particular 0.001 to 60 wt .-%.

The amount of agents or concentrates used depends on the type and type come from insects and depending on the medium. The optimal amount to use can be determined by test series in the application. Generally in my opinion, however, it is sufficient 0.0001 to 20% by weight, preferably 0.001 to 10 wt .-%, of the active ingredient, based on the material to be protected.

An organic chemical solvent serves as the solvent and / or diluent solvent or solvent mixture and / or an oily or oily heavy 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.

The organic chemical solvents used are preferably oily or oily ones Solvents with an evaporation number above 35 and a flash point above half 30 ° C, preferably above 45 ° C, used. As such volatile, water-insoluble, oily and oily solvents become corresponding mine ralöle or their aromatic fractions or mineral oil-containing solvent mixtures cal, preferably white spirit, petroleum and / or alkylbenzene used.

Mineral oils with a boiling range of 170 to 220 ° C are advantageous, test petrol with a boiling range of 170 to 220 ° C, spindle oil with a boil range from 250 to 350 ° C, petroleum or aromatics with a boiling range of 160 up to 280 ° C, turpentine oil and the like.  

In a preferred embodiment, liquid aliphatic hydrocarbons substances with a boiling range of 180 to 210 ° C or high-boiling mixtures of aromatic and aliphatic hydrocarbons with a boiling range from 180 to 220 ° C and / or spindle oil and / or monochloronaphthalene, preferably two se α-monochloronaphthalene used.

The organic non-volatile oily or oily solvents with a Evaporation rate above 35 and a flash point above 30 ° C, preferably above 45 ° C, can be partly due to slightly or medium volatile organic Mix solvent to be replaced, provided that the solvent mix also 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.

According to a preferred embodiment, part of the organic chemical Solvent or solvent mixture through an aliphatic polar orga niche chemical solvent or solvent mixture replaced. Preferably come alipha containing hydroxyl and / or ester and / or ether groups organic chemical solvents such as glycol ether, esters or the like for use.

As an organic chemical binder in the present Er finding the known water-dilutable and / or in the used organic chemical solvents soluble or dispersing or emul gable synthetic resins and / or binding drying oils, especially binders consisting of or containing an acrylic resin, a vinyl resin, e.g. B. 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 Resin used.

The synthetic resin used as a binder can be in the form of an emulsion, disper sion or solution. Bitumen or bituminous substances up to 10 wt .-%, are used. In addition, you can dyes, pigments, water-repellants, odor correctors known per se tien and inhibitors or corrosion protection agents and the like. Be used.  

According to the invention, preference is given to organic chemical binders least an alkyd resin or modified alkyd resin and / or a drying one vegetable oil contained in the medium or in the concentrate. According to the invention alkyd resins with an oil content of more than 45 wt .-%, preferably as 50 to 68 wt .-%, used.

The binder mentioned can be wholly or partly by a fixation medium (mixture) or a plasticizer (mixture) can be replaced. These additions should volatilize the active ingredients and crystallize or from prevent cases. 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, glycerol ether or higher molecular weight Gly kolether, glycerol ester and p-toluenesulfonic acid ester.

Fixing agents are chemically based on polyvinyl alkyl ethers such as. B. 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 organic chemical solvents or diluents, emulsifiers and dispersers gators.

A particularly effective wood protection is provided by industrial impregnation drive, e.g. B. vacuum, double vacuum or printing process.

The ready-to-use agents can optionally also be other insecticides and optionally contain one or more fungicides.

The additional mixing partners are preferably those in WO 94/29 268 Insecticides and fungicides mentioned in question. The ones mentioned in this document Connections are an integral part of this application.  

Insecticides such as chloropyriphos, phoxime, silafluofin, alphamethrin, cyfluthrin, cypermethrin, delta methrin, permethrin, imidacloprid, M-25, flufenoxuron, hexaflumuron and tri flumuron are particularly preferred mixing partners.
as well as fungicides such as epoxyconazole, hexaconazole, azaconazole, propiconazole, tebuconazole, cyproconazole, metconazole, imazalil, dichloffluanid, tolylfluanid, 3-iodo-2-propynylbutylcarbamate, N-octyl-isothiazolin-3-n-one and 4,5 called -octylisothiazolin-3-one.

The manufacture and use of the active compounds according to the invention start out the following examples.

Manufacturing examples example 1 (Method B)

0.50 g (1.25 mmol) N- (3-ethyl-4-chloro-isothiazolyl) -4- (4-cyanophenoxy) phenyl Acetic acid amide and 0.97 g (3.26 mmol) Lawessons reagent in 20 ml of toluene Boiled under reflux for 7 hours, concentrated and the crude product using columns Chromatography on silica gel (eluent: methylene chloride) cleaned.

0.16 g (31% of theory) is obtained. N- (3-Ethyl-4-chloro-isothiazolyl) -4- (4-cyano-phenoxy) phenylacetic acid-e-thioamide.

Melting point: 177-178 ° C.  

Examples of use Example A

Phaedon larval test
Solvent: 7 parts by weight of dimethylformamide
Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To prepare a suitable preparation of active compound, 1 Ge is mixed most of the active ingredient with the specified amount of solvent and the specified amount of emulsifier and dilute the concentrate with water to the wanted concentration.

Cabbage leaves (Brassica oleracea) are dipped into the active ingredient preparation the desired concentration and treated with horseradish leaf beetle larvae Phaedon cochleariae occupied while the leaves are still moist.

After the desired time, the kill is determined in%. Here means 100% that all beetle larvae have been killed; 0% means that no beetles Larvae were killed.

In this test, z. B. the connection of preparation example 1 an exemplary active ingredient concentration of 0.1% a kill of 100% after 7 days.

Claims (7)

1. Compounds of formula (I) in which
R¹ represents alkyl, haloalkyl, alkoxyalkyl, alkylthioalkyl, alkoxy, alkylthio or optionally substituted cycloalkyl,
R² represents hydrogen, halogen, cyano, nitro, thiocyanato, alkoxycarbonyl, alkenyloxycarbonyl, alkylthio, haloalkylthio, alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, haloalkylsulfonyl or thiocarbamoyl,
R³ represents hydrogen alkyl, haloalkyl, alkoxyalkyl, alkylcarbonyl, alkylsulfonyl, in each case optionally substituted arylcarbonyl, arylsulfonyl or arylalkyl or optionally substituted cycloalkyl,
R⁴ represents optionally substituted aryl, optionally substituted cycloalkyl or optionally substituted cycloalkenyl and
Y represents optionally substituted alkylene, alkenylene or alkylene oxy. 2. A process for the preparation of compounds of formula (I) according to claim 1, characterized in that

• A) compounds of the formula (II) in which
  R¹, R² and R³ have the meaning given above,
  • a) with compounds of the formula (III) R⁴-Y-CS-G (III) in which
    R⁴ and Y have the meaning given above and
    G represents a leaving group, e.g. B. for halogen (especially chlorine), imidazolyl, benzimidazolyl, 1,2,4-triazolyl, pyrazolyl or benztriazolyl,
    or
  • b) with dithioesters of the formula (IV) Alk-S-CS-Y-R⁴ (IV) in which
    R⁴ and Y have the meaning given above and
    Alk represents alkyl (e.g. methyl or ethyl) or CH₂COOM, where
    M represents an alkali metal (e.g. sodium or potassium),
    if appropriate in the presence of a base and if appropriate in the presence of a diluent;
    or
• B) Compounds of the formula (V) in which
  R¹, R², R³, R⁴ and Y have the meaning given above,
  with a sulfurizing agent, if appropriate in the presence of a diluent.

3. pesticide, characterized by a content of min at least one compound of formula (I) according to claim 1. 4. Use of compounds of formula (I) according to claim 1 for Pest control. 5. A method for controlling pests, characterized in that compounds of formula (I) according to claim 1 on pests and / or let their living space take effect. 6. Process for the preparation of pesticides, thereby ge indicates that compounds of the formula (I) according to Claim 1 mixed with extenders and / or surfactants. 7. Use of compounds of formula (I) according to claim 1 for the preparation provision of pesticides.