WO1998002424A1 - 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, R2, R3, R4¿, and Y have the meanings given in the description, methods of manufacturing them, and their use to combat animal pests.

Description

Substituted N- (5-isothiazolvD-thioarnide

The present invention relates to new substituted N- (5-isothιazolyl) thioamido processes for their preparation and their use for controlling animal pests

It is already known that certain N- (5-isothιazolyl) amide insecticidal properties have properties (see, for example, WO 95/3] 448 and DE 195 42 372).

The effectiveness and range of action of these compounds is, however, not always completely satisfactory, especially at low application rates and concentrations

New substituted N- (isothιazolyl) thιoamιde of formula (I) have been found.

R 'R'

N CS. ^ R ⁴ (I)

^* Y

in which

R ^{1 represents} alkyl, haloalkyl, alkoxyalkyl, alkylthioalkyl, alkoxy, alkylthio or optionally substituted cycloalkyl,

R ^{2 represents} hydrogen, halogen, cyano, nitro, thiocyanato, alkoxycarbonyl, alkenyloxycarbonyl, alkylthio, haloalkylthio, alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, haloalkylsulfonyl or thiocarbamoyl,

R "represents hydrogen, alkyl, haloalkyl, alkoxyalkyl, alkylcarbonyl, alkylsulfonyl, in each case optionally substituted arylcarbonyl, arylsulfonyl or arylalkyl or optionally substituted cycloalkyl,

R ^{4 represents} optionally substituted aryl, optionally substituted cycloalkyl or optionally substituted cycloalkenyl and Y represents optionally substituted alkylene, alkenyl or alkyleneoxy.

It has also been found that the compounds of the formula (I) can be obtained if

A) compounds of the formula (II)

in which

R \ R ² and R ^? the above ang

a) with compounds of the formula (III)

R ⁴ -Y-CS-G (III)

in which

R ⁴ and Y have the meaning given above and

G represents a leaving group, for example halogen

(especially chlorine), imidazolyl, benzimidazolyl. 1,2,4-triazolyl, pyrazolyl or benzotriazolyl,

or

b) with dithioesters of the formula (IV)

Alk-S-CS-YR ⁴ (IV)

in which

R ⁴ and Y have the meaning given above and Alk represents alkyl (for example methyl or ethyl) or CH ₂ COOM, where

M represents an alkali metal (for example 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

R ¹ , R ² , R \ R ⁴ 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 the formula (I) have highly pronounced biological properties and above all for controlling animal pests, in particular insects, arachnids and nematodes, which are used in agriculture, in the forests, in the stock and Protect material and occur in the hygiene sector, are suitable

Surprisingly, the substituted N- (5-isothiazol-yl) thioamides according to the invention have a considerably better activity against animal pests than the constitutionally similar known compounds

The compounds according to the invention are generally defined by the formula (I). Preferred substituents or ranges of the radicals listed in the formulas mentioned above and below are explained below

R ¹ preferably represents C _| -C ₄ -Alky], C _| -C ₄ -Halogenalkyl with 1 to 5 identical or different halogen atoms, such as fluorine, chlorine and bromine atoms, C _r C ₄ -alkoxy-C _r C ₄ -alkyl, C- -C ₄ -Alkylthιo-C _r C ₄ - alkyl, C, -C ₄ alkoxy,

CC ₄ -alkylthio or represents optionally mono- to trisubstituted by identical or different substituents from _{C] -C4} alkyl or halogen CC cyclo- -alkyl

R ² is preferably hydrogen, halogen, cyano, nitro, thiocyanato, C-- C ₄ -alkoxy-carbonyl, C ₂ -C ₄ -alkenyloxy-carbonyl, C, -C -alkylthioo, - -C, -

Haloalkylthio with 1 to 5 identical or different halogen atoms, such as fluorine and chlorine atoms, C _| -C ₄ -Alkylsulfιnyl, C - C -HalogenalkylsuI- finyl with 1 to 5 identical or different halogen atoms, such as fluorine and chlorine atoms, C - C ₄ -alkylsulfonyl, C - C ₄ -Haiogenalkylsulfonyl with 1 to 5 identical or various halogen atoms, such as fluorine and chlorine atoms or for thiocarbamoyl

R ¹ preferably represents hydrogen, C, -C ₄ -alkyl, C, -C ₄ -haloalkyl with 1 to 5 identical or different halogen atoms, such as fluorine and chlorine atoms, C _] -C ₄ -alkoxy-C, -C ₄ -alkyl, C, -C ₄ alkylcarbonyl, C, -C ₄ alkyl - sulfonyl, each optionally monosubstituted to trisubstituted, identically or differently, in phenylcarbonyl, phenylsulfonyl or benzyl, where in each case halogen, nitro, cyano , C, -C ₄ - alkyl, C, -C ₂ haloalkyl having 1 to 5 identical or different halogen atoms, such as fluorine and chlorine atoms, C _r C ₄ alkoxy, C, -C ₄ alkylthio, C, -C ₇ -haloalkoxy with 1 to 5 identical or different halogen atoms, such as fluorine and chlorine atoms or C - C ₂ -haloalkylthio with 1 to 5 identical or different halogen atoms, such as fluorine and chlorine atoms, or for single to triple, if appropriate, the same or different C 1 -C ₄ alkyl or halogen substituted C 1 -C ₆ cycloalkyl

R ⁴ preferably represents phenyl which is monosubstituted to trisubstituted identically or differently, the substituents being halogen, nitro, cyano, C _r C _{] 2} -alkyl, C, -C ₁₂ -haloalkyl having 1 to 5 identical or different halogen atoms, such as fluorine and chlorine atoms, C Cp-alkoxy, C - C ₁₂ haloalkoxy with 1 to 5 identical or different halogen atoms, such as fluorine and chlorine atoms, C, -C _p -alkylthio, C _p -halogenal- alkylthio with 1 to 5 identical or different halogen atoms, such as fluorine and chlorine atoms, CVC ₁₂ alkenyl, C ₂ -C _p -halogenalkenyl with 1 to 5 identical or different halogen atoms, such as fluorine and chlorato, optionally one to three times, identical or differently, by C, -C ₄ - alkyl or halogen substituted C ^ -C ₈ cycloalkyl and in each case optionally mono- to trisubstituted, in particular in the phenyl moiety by identical or different halogen, nitro, cyano, C, -C ₄ alkyl, C - -C ₄ -Halogen- alkyl with 1 to 5 identical or different halogen atoms, such as fluorine and chlorine atoms, C _t -C -alkoxy, C, -C ₄ -haloalkoxy with 1 to 5 identical or different halogen atoms, such as fluorine and chlorine atoms C _| -C ₄ - alkylthio, C- -C ₄ haloalkylthio with 1 to 5 identical or different halogen atoms, such as fluorine and chlorine atoms, CpC ₄ alkylthioo-C, -C, -alkyl

C- -C ₄ alkylsulfonyl, C - C ₄ -haloalkylsulfonyl having 1 to 5 identical Odei different halogen atoms, such as fluorine and chlorine atoms, C, -C ₄ alkyl carbonyl, C - C ₄ alkoxy-carbonyl, thiocarbamoyl, _C] -C _{4 -Alkoxιmιno-C]} - C, alkyl or optionally substituted by C, -C ₄ alkyl-substituted Oxdiazoly! substituted phenyl, phenoxy, phenylthio, benzyl or benzyloxy in

Question come, or for Eweιls optionally single to triple, the same or differently substituted C -C ₈ cycloalkyl or C <_; -C ₈ cycloalkenyl, the substituents being C- -C ₄ alkyl, C, -C ₄ haloalkyl having 1 to 5 identical or different halogen atoms, such as fluorine and chlorine atoms, C, -C ₄ -

Alkoxy, C _j -C ₄ haloalkoxy with 1 to 5 identical or different halogen atoms, such as fluorine and chlorine atoms, C -C ₈ cycloalkyl, and optionally single to triple, identical or different, by flalogen, cyano, nitro, C _r C _4- alkyl, C, -C ₄ -haloalkyl with 1 to 5 identical or different halogen atoms, such as fluorine and chlorine atoms, C - C ₄ -alkoxy or C, -C ₄ -haloalkoxy with 1 to 5 identical or different halogen atoms, how fluorine and chlorine atoms are substituted phenyl

preferably represents C _r C ₆ alkylene, C ₁ -C ₆ hydroxyalkylene, C, -C ₄ alkoxy C, -C ₆ -alkylene, C _| -C ₄ -alkylcarbonyloxy-C, -C ₆ -alkylene, cyano-C- -C ₆ -alkylene-, C, -C ₄ -haloalkylene with 1 to 5 identical or different halo- gene atoms such as fluorine and chlorine atoms; optionally single to triple, identical or different, substituted by fluorine, chlorine or methyl, CC-cycloalkyl-C, -C ₄ -alkylene, C ₂ -C ₄ -alkenylene or C _r C ₄ -alkyleneoxy.

R ¹ particularly preferably represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl; CH ₂ F, CHF ₂ , CF _λ , CH ₂ CI, CH ₂ Br, CHCICFF ,; Methoxy, ethoxy,

Methoxymethyl, ethoxymethyl; Methylthiomethyl or cyclopropyl.

R ² particularly preferably represents hydrogen, chlorine, bromine, cyano, nitro, thiocyanato; Methoxycarbonyl, ethoxycarbonyl, i-propoxycarbonyl, n-propoxycarbonyl; Allyloxycarbonyl, SCF ^, SCC1 ₂ F, SOCF- ^, SOCCUF, SO F ,, S0 CCI ₂ F, SCHF ₂ , SOCHF ₂ , S0 ₂ CHF ₂ or CSNH ₂ .

W particularly preferably represents hydrogen, methyl, ethyl, n- or i-propyl,

Methoxymethyl, ethoxymethyl, n-propoxymethyl, n-butoxymethyl; Methylcatbonyl, methylsulfonyl; each optionally mono- or disubstituted, identically or differently, by fluorine, chlorine, methyl or trifluoromethyl-substituted phenyl carbonyl or benzyl; or cyclopropyl

R particularly preferably represents phenyl which is monosubstituted to trisubstituted by identical or different substituents, the substituents being halogen, nitro, cyano, C - C _p -alkyl, C - C _p -haloalkyl having I to 5 identical or different halogen atoms, such as Fluorine and chlorine atoms, C - C alkoxy, C _r C ₄ haloalkoxy with 1 to 5 identical or different halogen atoms, such as fluorine and chlorine atoms, C _| -C ₄ alkylthio. C - C ₄ haloalkyl thio with 1 to 5 identical or different halogen atoms, such as fluorine and chlorine atoms, C ₂ -C ₄ alkenyl, C ₂ -C ₄ halo alkenyl with 1 to 5 identical or different halogen atoms, such as fluorine - And chlorine atoms, and in each case, if appropriate, once to three times, identically or differently

Halogen, nitro, cyano, C, -C ₄ alkyl, C - C ₄ halogen alkyl with 1 to 5 identical or different halogen atoms, such as fluorine and chlorine atoms, C, - C ₄ alkoxy, C, -C ₄ - Haloalkoxy with 1 to 5 identical or different halogen atoms, such as fluorine and chlorine atoms, C _r C ₄ alkylthio, C _r C ₄ haloalkylthio with 1 to 5 identical or different halogen atoms, such as

Fluorine or chlorine atoms, C, -C ₄ -alkylthio-C _r C ₄ -alkyl, C _r C ₄ -alkylsulfonyl, C, -C ₄ -haloalkylsulfonyl with 1 to 5 identical or different halogen atoms, such as fluorine or chlorine atoms, C , -C -alkyl-carbonyl, C _r C ₄ - Alkoxy-carbonyl, thiocarbamoyl, C _] -C ₄ -alkoximino-C _] -C, -alkyl or optionally substituted by C, -C _T alkyl l, 2,4-oxydazolyl-3-yl substituted phenoxy, phenylthio or benzyloxy in question come

Y is particularly preferably one of the groups

-CH ₂ -, -CH (CH) -, -CH (C ₂ H ₅ ) -, -CH (nC ₃ H ₇ ) -, -CH (iC, H ₇ ) -, -CH ₂ CH ₂ -, - CH (OH) -, -CH (OCH ₃ ) -, -CH (0-CO-CH ₃ ) -, -CH (CN) -, -CHF-, -CHC1-,

-CH -CH = CII- or -CH ₂ 0-, with the left side in each case

the group is linked to the thiocarbonyl group

R i very particularly preferably represents methyl, ethyl, n- or i-propyl, n-, i-,

10 s- or t-butyl, CH, F, CHF ₂ , CF ₃ , CH ₂ C1, CH ₂ Br, methoxy or ethoxy

R ^~ very particularly preferably represents hydrogen, chlorine, bromine, cyano, nitro, thiocyanato, methoxycarbonyl or ethoxycarbonyl

R ¹ very particularly preferably represents hydrogen, methyl, ethyl, methoxymethyl, ethoxymethyl, methylcarbonyl, phenylcarbonyl or methylsulfo-] ^ς ι nyl

R 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, 0 methylthio, CF ₃ , OCF ₃ , OCHF ₂ , SCF ₃ , SCC1 ₂ F, CH ₂ Br , CH ₂ C1 and 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, CF ₃ , OCF ₃ , OCHF ₂ , SCF ₃ , SCC1 ₂ F, CH ₂ Br,

25 CH ₂ CI, acetyl, ethylcarbonyl, methoxycarbonyl, methylsulfonyl, trifluoromethylsulfonyl, thiocarbamoyl, methoximinomethyl, l - (methoximino) - ethyl, l - (ethoximino) ethyl, l, 2,4-oxdiazol-3-yl or 5- Methyl-I, 2,4-oxodiazol-3-yl substituted phenoxy come into question.

Y very particularly preferably represents -CH ₂ - or -CH (CH ₃ ) -. Preferred compounds according to the invention are substances of the formulas (IA) or (IB)

in which

R ¹ , R ² and R ^? stand for the abovementioned general, preferred, particularly preferred and very particularly preferred meanings and

X ¹ , X ² , X \ X ⁴ and X ^s for the above under R ^{4 in} general, preferred, particularly preferred and very particularly preferred for the

Phenyl or phenoxy radical substituents are available and

X ¹ , X ² , X ³ and X ⁴ 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 NR'-CS-CH ₇ - or

NR -CS-CH (CH ₃ ) group, with particular preference being given to those compounds in which the substituents X ¹ , X ² , X ' ¹ and X ^{4 are} hydrogen

The general definitions or explanations of residues or explanations given above or in preferred areas apply to the end products and to the initial and intermediate products accordingly These residual definitions can be combined with one another as desired, that is, also between the respective preferred areas

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 there is a combination of the meanings listed above as being particularly preferred

According to the invention, the compounds of the formula are very particularly preferred

(I) in which there is a combination of the meanings listed above as being particularly preferred

In the radical definitions listed above and below, 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

In addition to the preparation examples, the following compounds of the formula (IC) may be mentioned individually

Table A

R 'R ^'

If, for example, 5-amino-4-chloro-3-ethyl-isothiazole and 4- (4-cyanophenoxy) -phenylthiooessionic acid chloride are used as starting materials in process (Aa), the course of the process according to the invention can be represented by the following reaction scheme

If, according to process (Ab), 5-amino-4-chloro-3-ethyl-thiazole and 4- (4-chlorophenoxy) -phcnyl-dio-thioessic acid methyl ester are used as starting materials, the course of the process according to the invention can be represented by the following reaction scheme

If, according to process (B), N- (4-chloro-3-ethyl - ^ - thιazolyl) -4- (4-cyanophenoxy) -phenylessιgsaureamιd is used as starting material and Lawesons reagent (2,4-Bιs- (4 -methoxyphenyl) -l, 3-dιthιa-2,4-diphosphetane-2,4-dιsulfid) as a sulfurizing agent, the course of the process according to the invention can be represented by the following reaction scheme

The N- (5-isothiazolyl) amides of the formula (II) required as starting materials for carrying out the processes (Aa) and (Ab) according to the invention are largely known (cf. the patent applications cited at the beginning) or can be prepared by the processes described therein

The compounds of the formula (III) which are furthermore to be used as starting materials in the process (Aa) according to the invention are generally known compounds of organic chemistry. In the formula (III) G preferably represents imidazolyl (cf. eg Liebigs Ann Chem 739, 201 (1970))

The dithioesters also required as starting materials for carrying out the process (Ab) according to the invention are generally defined by the formula (IV). In this formula (IV), Alk preferably represents methyl or CH ₂ COONa

The dithioesters of the formula (IV) are known (see, for example, Tetrahedron 2663 (1984), J Chem Research (M) 2701 (1988), Chem Ind (London) 803, 1974, Russ Chem Rev 45, 1035 (1976)) and / or can be produced by known, analog processes

The compounds of formula (V) required to carry out process (B) are known from the patent applications cited at the outset or can be prepared by the processes described there

The sulfurizing agents used in carrying out the process according to the invention

Process (B) preferably phosphorus pentasulfide or Lawesson's reagent [2,4- Bιs (4-methoxyphenyl) -l, 3,2,4-dιthiadιphosphetan-2,4-dιthιon] (see also Tetrahedron Vol 41, No 22, 5061 ff (1985)) in question Process (Aa) described above for the preparation of the compounds of the film (I) is 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, for example, cyclohexane, toluene _{, can} preferably be used _.

Chlorobenzene, chloroform, dichloromethane, dichloroethane, dioxane, tetrahydrofuran, diethyl ether or Acetonitπl

The process (Aa) described above for the preparation of the compounds of the 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)

Bases which can be used in process (Aa) are all customary proton acceptors. Alkali or alkaline earth metal hydroxides, alkali metal or alkaline earth metal carbonates or hydrogen carbonates or nitrogen bases can preferably be used. Examples include sodium hydroxide, calcium hydroxide, potassium carbonate, sodium hydrogen carbonate, triethylamine, dibenzylamine, diisopropylamine, Pvπdin

Chinohn, diazabicyclooctane (DABCO), diazabicyclonones (DBN) and diazabicycloundecene (DBU)

The reaction temperatures can be varied within a wide range in the process (Aa) described. In general, temperatures between -40 ° C. and + 200 ° C., preferably between 0 ° C. and 100 ° C.

When carrying out the process (Aa) described above for the preparation of the compounds of the formula (I), 1 to 2 mol, preferably 1 to 1.5 mol, of the compound of the formula (1) are generally employed per mol of 5-aminoisothiazole of the formula (II) III) a

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

The end products are worked up and isolated in a generally known manner Suitable diluents for carrying out the process (Ab) according to the invention are all customary solvents. Halogenated aliphatic or aromatic hydrocarbons, such as methylene chloride, dichloroethane, cyclohexane, toluene or chlorobenzene, can preferably be used

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

When carrying out the process (Ab) according to the invention, the reaction temperatures can be varied within a substantial range. In general, temperatures between 0 ° C. and 150 ° C., preferably between 20 ° C. and 120 ° C.

When carrying out the process (Ab) according to the invention, one sets per mole

Pyπdylamine of the formula (III) in general 1 to 3 mol, preferably 1 to 1, 5 mol of dithioester of the formula (IV). Working up and isolation are carried out by customary methods

Preferred diluents for carrying out process (B) according to the invention are hydrocarbons, such as toluene, xylene, tetralin

Hexane or cyclohexane in question

When carrying out process (B) according to the invention, the reaction temperatures can be varied within a substantial range. In general, temperatures between 0 ° C. and 200 ° C., preferably between 20 ° C. and 150 ° C.

When carrying out process (A) according to the invention, between 1 and 3 mol, preferably between 1 and 2 mol, of sulfurizing agent are generally employed per mol of compound of the formula (II). Working up is carried out by customary methods

The compounds of formula (I) can also be obtained by using 5-isothiazolyl isothiocyanates of formula (VI)

in which

R ¹ and R ^{2 have} the meaning given above,

with Gngnard compounds of the formula (VII)

Hal'-Mg-YR ¹ (VII)

in which

Hai 'represents halogen (especially chlorine or bromine) and

Y and R have the meaning given above,

implemented in the usual way (see also JACS 4849 (1955))

The N- (5-lsothιazolyl) thioamide of the formula (lα)

in which

R ¹ , R ² , R and R ^{4 have} the meaning given above,

can also be obtained by using 5-amino-thiazoles of the formula (III)

in which

R ¹ , R ² and R ^ have the meaning given above,

with carbonyl compounds of formula (VIII)

E-CO-CH ₂ -R ⁴ (VIII)

in whichi

E represents hydrogen or methyl and

R ^{4 has} the meaning given above,

in the presence of sulfur (see also Pet Chem USSR (Engl Transl) 345 (1993))

The substituted N- (5-isothιazolyl) thioamides of the formula (I) according to the invention can, if appropriate, be converted into their corresponding N-oxide or salt derivatives in a known manner and these are also the subject of the present application

With good plant tolerance and favorable warm-blood toxicity, the active substances are suitable for combating animal pests, in particular insects, arachnids and nematodes, which occur in agriculture, in forests, in the protection of stocks and materials and in the hygiene sector. They can preferably be used as crop protection products effective against normally sensitive and resistant species as well as against all or individual stages of development The pests mentioned above include From the order of the Isopoda, for example Oniscus asellus, Armadillidium vulgare, Porcellio scaber

From the order of the Diplopoda, for example, Blaniulus guttulatus

From the order of the Chilopoda, for example Geophilus carpophagus, Scutigera spec

From the order of the Symphyla eg Scutigerella Immaculata

From the order of the Thysanura, for example Lepisma saccharina

From the order of the Collembola B Onychiurus armatus

From the order of the Orthoptera, for example Blatt oπcntalis, Peπplancta ameπcana Leucophaea maderae, Blattella germanica, Acheta domesticus, Gryllotalpa sp, Locusta migratoπa migratoπoides, Melanoplus differentialis, Schistocerca gregana

From the order of the Dermaptera eg Forficula auπculaπa

From the order of the Isoptera, for example Reticuhtermes spp

From the order of the Anoplura, for example Pediculus humanus corpons Haematopmus spp, Linognathus spp

From the order of the Mallophaga, for example Tπchodectes spp, Damalinea spp

From the order of the Thysanoptera, for example Hercinothrips femoralis, Thπps tabaci

From the order of Heteroptera e.g. Eurygaster spp, Dysdercus intermedius, Piesma quadrata, Cimex lectulaπus, Rhodnius prolixus, Tπatoma spp

From the order of the Homoptera, for example Aleurodes brassicae, Bemisia tabaci, Tπaleurodes vaporanorum, Aphis gossypii, Brevicoryne brassicae, Cryptomyzus πbis, Aphis fabae, Aphis pomi, Eπosoma lanigerum, Hyalopterus arundinis, Phylloxemaxphiphosum, Phppoxera macrophorus, sppaoxemphiphidumx humuh, Rhopalosiphum padi, Empoasca spp, Euscehs bilobatus, Nephotettix cincticeps, Lecanium corni, Saissetia oleae, Laodelphax stnatellus, Nilaparvata lugens, Aonidiella aurantn, Aspidiotus hederae, Pseudococcus spp, Psylla spp

From the order dei Lepidoptera, for example Pectinophora gossypiella, Bupalus pinianus, Cheimatobia brumata, Lithocolletis blancardella, Hyponomeuta padella, Plutella aculipennis, Malacosoma neustπa, Euproctis chrysorrhoea, Lymantπa spp,

Bucculatπx thurbenella, Phyllocnistis citrella, Agrotis spp, Euxoa spp, Feltia spp, Eaπas insulana, Heliothis spp, Spodoptera exigua, Mamestra brassicae, Panohs flammea, Spodoptera litura, Spodoptera spp, Tπchoplusiao sil, Tπchoplusiao npp , Ephestia kuehniella, Galleπa mellonella, Tineola bisselliella, Tinea pelhonella, Hofmannophila pseudospretella,

Cacoecia podana, Capua reticulana, Choπstoneura fumiferana, Clysia ambiguella 1 lomona magnanima, l ortriλ viπdana

From the order of the Coleoptera e.g. Anobium punctatum, Rhizopertha dominica, Bruchidius obtectus, Acanthoscehdes obtectus, Hylotrupes bajulus, Agelastica alni, Leptinotarsa decemlineata, Phaedon cochleaπae, Diabrotica spp, Psvlliodalaπysoil Sitophilus spp, Otiorrhynchus sulcatus, Cosmopohtes sordidus, Ceuthorrhynchus assimihs, Hypera postica, Dermestes spp, Trogoder a spp, Anthrenus spp, Attagenus spp, Lyctus spp, Mehgethes aeneus, Ptinus psoho, Ptiolebumbohbi, sidesbum, Sides spp, Conoderus spp, Melolontha melolontha, Amphimallon solstitiahs, Costelytra zealandica

From the order of Hymenoptera, for example Dipπon spp, Hoplocampa spp, Lasius spp, Monomoπum pharaonis, Vespa spp

From the order of Diptera, for example Aedes spp, Anopheles spp,

spp,

Drosophila melanogaster, Musca spp, Fannia spp, Calhphora erythrocephala, Lucilia spp, Chrysomyia spp, Cuterebra spp, Gastrophilus spp, Hyppobosca spp, Stomoxys spp, Oestrus spp, Hypoderma spp, Tabanus spp, Tanniaulppia sppanppella hppiappella, Bibio , Pegomyia hyoscyami, Ceratitis capitata, Dacus oleae, Tipula paludosa

From the order of the Siphonaptera, for example Xenopsylla cheopis, Ceratophyllus spp From the order of the Arachnida, for example Scorpio maurus, Latrodectus mactans.

From the order of the Acarina, for example Acarus siro, Argas sp, Ornithodoros spp, Dermanyssus gallinae, Eriophyes ribis, Phyllocoptruta oleivora, Boophilus spp, Rhipicephalus spp., Amblyomma spp, Hyalomma spp, Ixodes spp, Psoroptes spp, Choricoptes spp, Choricoptes spp, Chori Tarsonemus spp, Bryobia praetiosa,

Panonychus spp, Tetranychus spp

Plant parasitic nematodes include, for example, Pratylenchus spp, Radopholus similis, Ditylenchus dipsaci, Tylenchulus semipenetrans, Heterodera sp, Globodera spp, Meloidogyne spp, Aphelenchoides spp, Longidorus spp, Xiphinema spp, Trichodor spp

The compounds of the formula (I) according to the invention are notable in particular for high insecticides and acaricidal activity

They can be used with particularly good success for combating plant-damaging insects, such as, for example, against the horseradish leaf beetle larvae (Phaedon cochlaeriac), the caterpillars of the green cockroach (Plutella maculipennis)

Rice cicada (Nephotettix cinctπceps) and the caterpillars of the owl butterfly (Spodoptera frugiperda) or for combating plant-damaging mites, such as against the common spider mite (Tetranychus urticae)

The active ingredients can be converted into the customary formulations, such as solutions, emulsions, wettable powders, suspensions, powders, dusting agents, pastes, soluble powders, granules, suspension emulsion concentrates, active ingredient-impregnated natural and synthetic substances and very fine encapsulations in polymers Fabrics

These formulations are prepared in a known manner, for example by mixing the active ingredients with extenders, that is to say liquid solvents and / or solid carriers, if appropriate using surface-active agents, that is to say emulsifiers and / or dispersants and / or foam-generating agents

If water is used as an extender, organic solvents can, for example, also be used as auxiliary solvents come essentially into question aromatics, such as xylene, toluene, or alkyl naphthalenes, chlorinated aromatics and chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chlorethylenes or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, for example 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 dimethyl form am id and dimethyl sulfoxide, and water

Possible solid carriers are, for example, ammonium salts and natural rock powders such as kaolins, clays,

Talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and synthetic rock flour, such as highly disperse silica, aluminum oxide and silicates, as solid carrier materials for granules are, for example, broken and fractionated natural rocks such as calcite, marble, pumice, sepiolite, dolomite and synthetic Granules from inorganic and organic flours as well

Granules of organic material such as sawdust, coconut shells, corn cobs and tobacco stalks, emulsifiers and / or foam-producing agents are suitable, for example nonionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example alkylaryl polyglycol ethers, Alkyl sulfonates, alkyl sulfates, aryl sulfonates and protein hydrolyzates, as dispersants are, for example, lignin sulfite waste liquors and methyl cellulose

Adhesives such as carboxymethyl cellulose, natural and synthetic polymers in the form of powders, granules or latices, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, and natural phospholipids such as cephalins and lecithins and synthetic phospholipids can be used in the formulations

Other additives can be mineral and vegetable oils

Dyes such as inorganic pigments, for example 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 in general contain between 0.1 and 95% by weight of active compound, preferably between 0.5 and 90% The active compound according to the invention can be present in its commercially available formulations and in the use forms prepared from these formulations in a mixture with other active compounds, such as insecticides, attractants, stenlants, bactericides, acanzides, nematicides, fungicides, growth-regulating substances or herbicides. The insecticides include, for example, phosphorus acid esters, carbamates, carboxylic acid esters, chlorinated hydrocarbons, phenylureas, substances produced by microorganisms and others

The following are particularly advantageous mixed partners

Fungicides: 2-aminobutane, 2-anion-4-methyl-6-cyclopropyl-pyπmιdιn, 2 ', 6'-dιbι omo-2-methyl-4'-tπfluoromethoxy-4'-tι ιfluoro-methyl-l, 3-thιazoi-5-caι boxanιlιd, 2,6-Dι- chloro-N- (4-tπfluoromethylbenzyl) -benzamιd, (E) -2-methoxyιmιno-N-methyl-2- (2-phenoxyphenyl) -acetamιd, 8th -Hydroxyquιnolιnsulfat, methyl- (E) -2- {2- [6- (2-cyano-phenoλy) -pyπmιdιn-4-yloxy] -phenyl} -3-methoxyacrylate, M ethyl - (E) -methoxιmιno- [alpha - (o-tolyloxy) -o-tolyl] acetate, 2-phenylphenol (OPP), aldimorph, ampropylfos,

Anilazine, azaconazole,

Benalaxyl, Benodanil, Benomyl, Binapacryl, Biphenyl, Bitertanol, Blasticidin-S, Bromuconazole, Bupiπmate, Buthiobate,

Calcium polysulfide, captafol, captan, carbendaziin, carboxin, chomomethionate (quinomethionate), chloroneb, chloropicπn, chlorothalonil, chlozohnate, cufraneb,

Cymoxanil, cyproconazole, cyprofuram,

Dichlorophen, diclobutrazole, diclofluanid, diclomezin, dicloran, diethofencarb, difenoconazole, dimethiπmol, di ethomorph, diniconazole, dinocap, diphenylamine, dipythion, ditahmfos, dithianon, dodine, drazoxolon

Edifenphos, Epoxyconazole, Ethiπmol, Etπdiazol,

Fenaπmol, Fenbuconazole, Fenfura, Fenitropan, Fenpiclonil, Fenpropidin, Fen- propimorph, Fentmacetat, Fentinhydroxyd, Ferbam, Feπmzone, Fluazinam, Fludi- oxonil, Fluoromide, Fluquinconazolc, Flusilazole, Flusulfamide, Folpetol, Aluminum-Flutolanilet, Fluutolanilet Fthahde, Fubeπdazol, Furalaxyl, Furmecyclox, Guazatine,

Hexachlorobenzene, hexaconazole, hymexazole,

Imazahl, Imibenconazol, Iminoctadin, Iprobefos (IBP), Iprodion, Isoprothiolan,

Kasugamycin, copper preparations such as copper hydroxide, copper naphthenate, copper oxychloride, copper sulfate, copper oxide, oxine copper and Bordeaux mixture,

Mancopper, Mancozeb, Maneb, Mepanipyπm, Mepronil, Metalaxyl, Metconazol, Methasulfocarb, Methfuroxain, Metiram, Metsulfovax, Myclobutanil,

Nickel dimethyldithiocarbamate, Nitrothal isopropyl, Nuaπmol,

Ofurace, Oxadixyl, Oxamocarb, Oxycarboxm,

Pefurazoat, Penconazol, Pencycuron, Phosdiphen, Phthalid, Pimaπcin, Piperalin, Polycarbamate, Polyoxin, Probenazol, Prochloraz, Procymidon, Propamocaib, Propiconazole, Propineb, Pyrazophos, Pyπfenox, Pyπmethanil, Pyroquilon,

Quintozen (PCNB),

Sulfur and sulfur preparations,

Tebuconazole, Tecloftalam, Tecnazen, Tetraconazole, Thiabendazole, Thicyofen, Thiophanat-methyl, Thiram, Tolclophos-methyl, Tolylfluamd, Tπadimefon, Tπadimenol, Tπazoxid, Tπchlamid, Tπcyclazol, Tπdemorphol, Tπdemorphol, Tπ

Vahdamycin A, Vinclozohn,

Zineb, ziram Bactericides:

Bronopol, dichlorophene, nitrapyπn, nickel dimethyldithiocarbamate, kasugamycin, octhilinone, furan carboxylic acid, oxytetracycline, probenazole, streptomycin, tecloftalam, copper sulfate and other copper egg preparations

Insecticides / acaricides / nematicides:

Abamectin, AC 303 630, Acephat, Acπnathπn, Alanycarb, Aldicarb, Alpha-methπn, Amitraz, Avermectin, AZ 60541, Azadirachtin, Azinphos A, Azinphos M, Azocyclotin,

Bacillus thunngiensis, Bendiocarb, Benfuracaib, Bensultap, Betacyfluthπn, Bifen- thπn, BPMC, Brofenprox, Bromophos A, Bufencaib, Buprofezin, Butocarboxin,

Butylpyπdaben,

Cadusafos, Carbaryl, Carbofuran, Carbophenothion, Carbosulfan, Cartap, CGA 1 57 419, CGA 184699, Chloethocarb, Chlorethoxyfos, Chlorfenvinphos, Chlorflu- azuron, Chlormephos, Chlorpyπfos, Chlorpyπfos M, Cis-Resmethπoth, Clofπnopnin, Clofπnopinin, Clofinopinin , Cyhalothπn, Cyhexatin,

Cypermethπn, cyromazine,

Deltamethπn, Demeton M, Demeton S, Demeton-S-methyl, Diafenthiuron, Diazinon, Dichlofenthion, Dichlorvos, Dicliphos, Dicrotophos, Diethion, Diflu- benzuion, Dimethoat, Dimethylvinphos, Dioxathion, Disulfoton,

Edifenphos, Emamectin, Esfenvalerat, Ethiofencarb, Ethion, Ethofenprox, Ethoprophos, Etπmphos,

Fenamiphos, Fenazaquin, Fenbutatinoxid, Fenitrothion, Fenobucarb Fenothiocarb, Fenoxycarb, Fenpropathπn, Fenpyrad, Fenpyroximat, Fenthion, Fenvalerate, Fipronil, Fluazinam, Flucycloxuron, Flucythrinat, Flufenoxuron, Flufenproxophon, Fufonproxophon, Fufonproxophon, Fufonproxophon, Fufonproxophon, Fufonfox, Fufion, Fufion, Fufone

HCH, heptenophos, hexaflumuron, hexythiazox,

Imidaclopπd, Iprobefos, Isazophos, Isofenphos, Isoprocarb, Isoxathion, Ivermectin, Lambda-cyhalothπn, Lufenuron, Malathion, Mecarbam, Mervinphos, Mesulfenphos, Metaldehyde, Methacπfos, Methamidophos, Methidathion, Methiocarb, Methomyl, Metolcarb, Milbemectin, Monocrotophos, Moxidectin,

Naled, NC 184, NI 25, Nitenpyram,

Omethoate, Oxa yl, Oxydemethon M, Oxydeprofos,

Parathion A, Parathion M, Permethπn, Phenthoat, Phorat, Phosalon Phosmet, Phosphamidon, Phoxim Piπmicarb, Piπmiphos M, Piπmiphos A Profenofos, Promecarb, Propaphos, Propoxur, Prothiofos, Prothoat, Pymetrozin, Pvadachaphenphion, Pyrvithachidophion, Pvrachaphthiophion, Pvrachaphrinophion, Pvrachaphrinophion, Pvrachaphthiophion, Pyπproxifene

Quinalphos,

I I 5992,

Salithion, Sebufos Silafluofen, Sulfotep, Sulprofos,

Tebufenozid, Tebufenpyrad, Tebupiπmphos, Teflubenzuron, Tefluthπn, Temephos, Terbam, Terbufos, Tetrachlorvinphos, Thiafenox, Thiodicarb, Thiofanox, Thio-methon, Thionazin, Thuπngiensin, Talomethathonon, Talomethathonon, Talomethathonon

Vamidothion, XMC, Xylylcarb, YI 5301/5302, Zetamethπn

A mixture with other known active ingredients, such as herbicides or with fertilizers and growth regulators, is also possible

The active compounds according to the invention can also be present in their commercially available formulations and in the use forms prepared from these formulations in a mixture with synergists. Synergists are compounds by which the action of the active compounds 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 The application 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

When used against hygiene and storage pests, the stands out

Active ingredient with an excellent residual effect on wood and clay as well as a good alkali stability on limed substrates

The active compounds according to the invention act not only against plant, hygienic and void pests, but also in the veterinary sector against animal parasites (ectoparasites) such as tick ticks, leather ticks and rough mites

Running mites, flies (stinging and licking), parasitic fly larvae, lice, lice, feather hangings and fleas These parasites include

From the order of the Anopluπda eg Haematopmus spp, Linognathus spp Pediculus spp, Phtirus spp, Solenopotes spp

From the order of the Mallophagida and the subordinates Amblyceπna as well

Ischnoceπna z B Tπmenopon spp, Menopon spp, Tnnoton spp, Bovicola spp, Werneckiella spp, Lepikentron spp, Damalina spp, Tnchodcctes spp, Felicola spp

From the order Diptera and the subordinates Nematoceπna and Brachyceπna 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 spp, Philipomyia spp, Braula spp, Musca spp, Hydrotaea spp, Stomoxys spp, Moratellia spp, Haematobia spp, Haematobia spp , Glossina spp, Calliphora spp, Lucilia spp, Chrysomyia spp, Wohlfahrtia spp, Sarcophaga spp, Oestrus spp, Hypoderma spp, Gasterophilus spp, Hippobosca spp, Lipoptena spp, Melophagus spp

From the order of the Siphonapteπda, for example Pulex spp, Ctenocephalides spp, Xenopsylla spp, Ceratophyllus spp From the order of the Heteropteπda, for example Cimex spp, Tπatoma spp, Rhodnius spp, Panstrongylus spp

From the order of the Blattaπda, for example Blatta oπentalis, Peπplancta ameπcana, Blattela germanica, Supella spp

From the subclass of the Acaπa (Acarida) and the orders of the Meta and

Mesostigmata z. B. Argas spp, Ornithodorus spp, Otobius spp, Ixodes spp, Amblyomma spp, Boophilus spp, Dermacentor spp, Haemophysalis spp, Hyalomma spp, Rhipicephalus spp, Dermanyssus spp, Railhetia spp, Pneumonyroostus spp, Pneumonyroostus spp

From the order dei Actinedida (Prostigmata) and Acaπdtda (Astigmata) / B

Acarapis spp, Cheyletiella spp, Ornithocheyletia spp, Myobia spp, Psoiergates spp, Demodex spp, Trombicula spp, Listrophorus spp, Acarus spp, Tyiophagus spp, Caloglyphus spp, Hypodectes spp, Pterolichus spp, Choroptes spp, Psoroptes spp, Psoroptes spp, Psoroptes spp, Psoroptes spp, Psoroptes spp, Choropes spp, Psoroptes spp , Notoedres spp, Knemidocoptes spp, Cytodites spp, Laminosioptes spp

The active compounds of the formula (I) according to the invention are also suitable for combating arthropods which are farm animals, such as, for example, cattle, sheep, goats, horses, pigs, donkeys, camels, buffalo, rabbits, chickens, turkeys, ducks, geese, bees , other domestic animals such as dogs, cats, house birds, aquarium fish and so-called experimental animals such as hamsters, guinea pigs, rats and mice. By fighting these arthropods death cases and reduced performance (in meat, milk, wool, skin, eggs , Flonig, etc.) can be reduced, so that the use of the active compounds according to the invention enables more economical and simple animal husbandry

The active compounds according to the invention are used in the veterinary sector in a known manner by enteral administration in the form of, for example, tablets, capsules, drinks, drenches, granules, pastes, boluses, the feed-through method, suppositories, by parenteral administration, for example by Injections (intramuscular, subcutaneous, intravenous, intraperitonal, etc.), 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 help of shaped bodies containing active ingredients, such as collars, ear tags, tail tags, limb tapes, holsters, marking devices, etc

When used for cattle, poultry, domestic animals, etc., the active compounds of the formula (I) can be used as formulations (for example powders, emulsions, flowables)

Agents), which contain the active substances in an amount of 1 to 80% by weight, directly or after 100 to 10,000-fold dilution or use them as a chemical bath

It has also been found that the compounds according to the invention have a high insecticidal activity against insects which destroy industrial materials

The following insects may be mentioned by way of example and preferably, but without limitation

Beetle like

Hylotrupes bajulus, Chlorophorus pilosis, Anobium punctatum, Xestobium rufovillosum, Ptilinus pecticornis, Dendrobium pertinex, Ernobius molhs, Pπobium carpini, Lyctus brunneus, Lyctus afπcanus, Lyctus planicolhs, Lyctus Trogoneus specus, Lyctus hnoxidium specus, Lybus specimen monachus, Bostrychus capucins, Hetcrobostrychus brunneus, Sinoxylon spec Dinoderus minutus

Hautflieger like

Sirex juvencus, Urocerus gigas, Urocerus gigas taignus, Urocerus augur

Termites like

Kalotermes flavicollis, Cryptotermes brevis, Heterotermes indicola, Reticulitermes flavipes, Reticulitermes santonensis, Reticulitermes lucifugus, Mastotermes darwiniensis, Zootermopsis nevadensis, Coptotermes formosanus

Bristle tail like Lepisma sacchaπna In the present context, technical materials are understood to mean non-living materials, such as preferably plastics, adhesives, glues, papers and cartons, leather, wood and wood processing products and paints

The material to be protected against insect infestation is very particularly preferably wood and wood processing products

Wood and wood processing products, which can be protected by the agent according to the invention or mixtures containing it, are to be understood as examples. Lumber, wooden beams, railway sleepers, bridge parts, jetties, wooden vehicles, boxes, pallets, containers, telephone poles, wooden cladding, wooden windows and doors, plywood, chipboard, carpentry or Ilolz products, which are generally used in house construction or joinery

The active compounds can be used as such, in the form of concentrates or formulations which are generally customary, such as powders, granules, solutions, suspensions, ulcers or pastes

The formulations mentioned can be prepared in a manner known per se, for example by mixing the active compounds with at least one solvent or diluent, emulsifier, dispersant and / or binder or fixative, water repellant, 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 of use 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 to 10% by weight of the active ingredient, based on the material to be protected

An organic-chemical solvent or solvent mixture and / or an oily or oil-like heavy substance serves as the solvent and / or diluent 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 oil-like solvents with an evaporation number above 35 and a flash point above 30 ° C., preferably above 45 ° C. Suitable mineral oils or their aromatic fractions or mineral oil-containing solvent mixtures are difficultly volatile, water-insoluble, oily and oil-like solvents. cal, preferably white spirit, petroleum and / or alkylbenzene used

Mineral oils with a boiling range of 170 to 220 ° C, white spirit with a boiling range of 170 to 220 ° C, spindle oil with a boiling range of 250 to 350 ° C, petroleum or aromatics with a boiling range of 160 to 280 ° C, turpentine oil are advantageous and the like for use

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

The organic semi-volatile oily or oil-like solvents with an evaporation number above 35 and a flash point above 30 ° C, preferably above 45 ° C, can be partially replaced by slightly or medium-volatile organic chemical solvents, with the proviso that the solvent mixture also has an evaporation number 35 and a flash point above 30 ° C, preferably above 45 ° C, and that the insecticide-fungicide mixture is soluble or emulsifiable in this solvent mixture

According to a preferred embodiment, part of the organic-chemical solvent or solvent mixture is replaced by an aphatic polar organic-chemical solvent or solvent mixture. Aliphatic organic-chemical solvents such as glycol ethers containing hydroxyl and / or ester and / or ether groups are preferably used , Ester or the like for use In the context of the present invention, the known organic-chemical binders are synthetic resins which are known to be water-thinnable and / or 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 rubber and / or synthetic resin

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-repellent agents, odorants and Inhibitors or corrosion protection agents and the like are used

According to the invention, 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 organic-chemical binder. According to the invention, alkyd resins with an oil content of more than 45% by weight, preferably 50, are preferred up to 68% by weight

All or part of the binder mentioned can be replaced by a fixative (gemιsch) or a plasticizer (gemιsch). These additives are intended to prevent volatilization of the active ingredients and crystallization or precipitation, preferably they replace 0.01 to 30% of the binder (based on to 100% of the binder used)

The plasticizers originate from the chemical classes of phthalic acid esters such as dibutyl, dioctyl or benzyl butyl phthalate, phosphoric acid esters such as tπbutyl phosphate, adipic acid esters such as di (2-ethylhexyl) adipate, stearates such as butyl stearate or amyl stearate, oleates such as butyl ether and olefinic glyceryl ether - Kolether, Glyceπnester and p-Toluenesulfonsaureestcr

Fixing agents are chemically based on polyvinyl alkyl ethers such as polyvinyl methyl ether or ketones such as benzophenone and 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 by large-scale impregnation processes, eg vacuum, double vacuum or printing processes

The ready-to-use compositions can optionally contain further insecticides and, if appropriate, one or more fungicides

Possible additional admixtures are preferably the insecticides and lungicides mentioned in WO 94/29 268. Those mentioned in this document

Connections are an integral part of this application

Insecticides, such as chloropyphosph, phoxime, silafluofin, Λlphamethπn, cyfluthπn, cypermethπn, delta-methπn, permethπn, imidaclopπd, NI-25, flufenoxuron, hexaflumuron and toxy-fungazazole, epoxy-fazazole, and epoxungazonole, as well as epifungazonole, as well as epoxungazon, as well as epoxungazon, as well as epifungazon, as Azaconazole, Propiconazole, Tebuconazole, Cyproconazole, Mctconazole, Imazalil, Dichlorfluanid, Tolylfluanid, 3-Iodo-2-propionyl-butylcarbamate N-octyl-ιsothιazolιn-3-oπ and 4,5-Dιchlor-N-octolιs called onolylsoth

The preparation and use of the active compounds according to the invention can be seen from the examples below

Manufacturing examples

example 1

(Method B)

0.50 g (1.25 mmol) of N- (3-ethyl-4-chloro-isothiazolyl) -4- (4-cyanophenoxy) phenylsacetic acid amide and 0.97 g (3.26 mmol) of Lawesson's reagent w are refluxed in 20 ml of toluene for 7 hours, concentrated and the crude product is purified by column chromatography on silica gel (mobile phase methylene chloride)

0.16 g (3.1% of theory) of N- (3-ethyl-4-chloro-isothiazolyl) -4- (4-cyano-phenoxy) -phenylacetic acid-thioamide is obtained

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 thi

To produce a suitable preparation of 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 egg to the desired concentration

Cabbage leaves (Brassica oleracea) are ^'I themselves in the preparation of active dei desired concentration treated and staffed with Meerrettichblattkafer larvae Phaedon cochleaπae as long as the leaves are still moist

After the desired time, the death rate is determined in%. 100% means that all the beetle larvae have been killed, 0% means that no beetle larvae have been killed

In this test, for example, the compound according to Preparation Example 1, with an exemplary active compound concentration of 0.1%, caused 100 deaths after 7 days

Claims

claims

1 compounds of formula (1)

in which

R ^{1 represents} alkyl, haloalkyl, alkoxyalkyl, alkylthioalkyl, alkoxy, alkylthio or optionally substituted cycloalkylene,

R ² for hydrogen, halogen, cyano, nitro, thiocyanato, alkoxycarbonyl, alkenyloxycarbonyl, alkylthio, haloalkylthio, klkyl ulfinyl, haloalkylsulfinyl, alkylsulfonyl. Haloalkylsulfonyl or thiocarbamoyl,

R 'represents hydrogen, alkyl, haloalkyl, alkoxyalkyl, alkylcarbonyl, alkylsulfonyl, and optionally optionally substituted arylcarbonyl, arylsulfonyl or arylalkyl or optionally substituted cycloalkyl,

R ⁴ for optionally substituted aryl, optionally substituted

Cycloalkyl or optionally substituted cycloalkenyl and

Y represents optionally substituted alkylene, alkenyl or alkyleneoxy

2 compounds of formula (I) according to claim 1, in which

R ¹ for C, -C ₄ alkyl, C _r C ₄ haloalkyl having 1 to 5 identical or different halogen atoms, such as fluorine, chlorine and bromine atoms, C _r C ₄ alkoxy-C _r C ₄ alkyl, C _r C ₄ -alkylthio-C _r C ₄ -alkyl, C, -C ₄ -alkoxy, C _r C ₄ -alkylthio or for optionally simple to three- CC ₆ cycloalkyl which is substituted once, identically or differently by C _r C ₄ alkyl or halogen,

R ² for hydrogen, halogen, cyano, nitro, thiocyanato, C, -C alkoxy oxycarbonyl, C ₂ -C ₄ alkenyloxy carbonyl, C, -C ₄ alkylthio, C, -C ₄ - haloalkylthio with 1 to 5 identical or different halogen atoms, such as fluorine and chlorine atoms, C, -C -alkylsulfionyl, C _j - -r haloalkylsulfinyl with 1 to 5 identical or different halogen atoms, such as fluorine and chlorine atoms, C, -C ₄ -alkylsulfonyl, C 1 -C 5 -HalogenalkylsulfoπyI with 1 to 5 identical or different halogen atoms, such as fluoi- and chloro atoms or i ur ^" I hio- caibamoyl,

R ^{1 is} hydrogen, C _r C ₄ -alkyl, C - C ₄ -haloalkyl having 1 to 5 identical or different halogen atoms, such as fluorine and chlorine atoms, C - C ₄ -alkoxy-C - C ₄ -alkyl, C - C, -Alkyl-carbonyl, C- -C - alkylsulfonyl, | eweιls optionally monosubstituted to trisubstituted in the phenylene or phenylcarbonyl, phenylsulfonyl or benzyl, where as substituents | eweιls halogen, nitro, cyano, C _] -C ₄ alkyl, C _] -C ₂ haloalkyl with 1 to 5 identical or different halogen atoms, such as fluorine and chlorine atoms, C _r C ₄ alkoxy, C, -C ₄ - Alkylthιo, C, -C ₂ haloalkoxy with 1 to 5 identical or different halogen atoms, such as fluorine and chlorine atoms or C - CVHalogenalkylthιo with I to 5 identical or different halogen atoms, such as fluorine and chlorine atoms, or for optionally simple to trisubstituted by identical or different C, -C ₄ alkyl or halogen-substituted C .-

C cycloalkyl,

R ^{4 is} phenyl which is monosubstituted to trisubstituted by identical or different substituents, the substituents being halogen, nitro,

Cyano, C - C ₁₂ alkyl, C, -C _{] 2} haloalkyl with 1 to 5 identical or different halogen atoms, such as fluorine and chlorine atoms, C, -

C _p -alkoxy, C _j -C _p -haloalkoxy with 1 to 5 identical or different halogen atoms, such as fluorine and chlorine atoms, C, -C _p - alkylthio, C, -C _{] 2} -haloalkylthio with 1 to 5 identical or vei - different halogen atoms, such as fluorine and chlorine atoms, C -.- C -, - Alkenyl, C ₂ -C _p -haloalkenyl with 1 to 5 identical or different halogen atoms, such as fluorine and chlorine atoms, optionally monosubstituted to triple, identically or differently, by C, -C -alkyl or halogen-substituted C ^ -C ₈ -cycloalkyl and each gegebe- 5 appropriate, mono- to trisubstituted by identical or different halogen, nitro, cyano, C, -C ₄ alkyl, C, -C ₄ -halogenoalkyl having 1 to 5 identical or different halogen atoms, such as fluorine and chlorine atoms, C , -C ₄ alkoxy, C - C haloalkoxy with 1 to 5 identical or different halogen atoms, such as fluorine and chlorine

10 atoms, C _| -C -Alkylthιo, C _| -C ₄ -Halogenalkylthιo with 1 to 5 identical or different halogen atoms, such as Pluoi - and chlorine atoms, C, -C ₄ -Alkylthιo-C, -C ₄ -alkyl, C, -C ₄ -Λlkylsulfonyl, CC haloalkylsulfonyl with 1 to 5 same or different halogen atoms, such as fluorine and chlorine atoms, C _| -C ₄ alkyl carbonyl C - -

1 5 C ₄ -alkoxy-carbonyl, thiocarbamoyl, C ₁ -C _{4 -Alkoxιmιno-C]} -C ₄ -alkvl Odei optionally substituted by C - C ₄ -Alkyi substituted oxdiazolyl substituted phenyl, phenoxy, phenylthio, benzyl or benzyloxy in question come, or for each if necessary up to triple, the same or

20 differently substituted C -C ₈ -cycloalkyl or C ₅ -C ₃ -cycloalkenyl, the substituents being C, -C ₄ -alkyl, C, -C ₄ -haloalkyl having 1 to 5 identical or different halogen atoms, such as fluorine and chlorine atoms, C - C ₄ alkoxy, C - C ₄ -IIalogenalkoxy with 1 to 5 identical or different halogen atoms, such as fluorine and

25 chlorine atoms, C ^ -C ₈ cycloalkyl, and optionally single to triple, the same or different by halogen, cyano, nitro, C, - C ₄ alkyl, C, -C ₄ haloalkyl with 1 to 5 identical or different halogen atoms , such as fluorine and chlorine atoms, C _] -C ₄ alkoxy or C _j -C ₄ haloalkoxy with 1 to 5 identical or different

30 halogen atoms, such as fluorine and chlorine atoms, substituted phenyl in

Question come and

Y for C, -C ₆ alkylene, C _r C ₆ hydroxyalkylene, C _r C ₄ alkoxy-C - C alkylene, C ₁ -C ₄ alkylcarbonyloxy-C, -C ₆ alkylene, cyano -C, -C ₆ alkyl-, C _] -C ₄ haloalkylene with 1 to 5 identical or different

35 halogen atoms, such as fluorine and chlorine atoms, optionally single to triple, the same or different by fluorine, chlorine or Methyl substituted C ₃ -C ₆ cycloalkyl-C _r C ₄ alkylene, C -, - C ₄ -alkenylene or C, -C ₄ alkyleneoxy.

Compounds of formula (I) according to claim 1, in which

R ^{1 is} methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl; CH-, F \ CHF ₂ , CF ^, CH ₂ C1, CH ₂ Br, CHCICH ,, methoxy, ethoxy, methoxymethyl, ethoxymethyl, methylthiomethyl or cyclopropyl,

R ² for hydrogen, chlorine, bromine, cyano, nitro, thiocyanato, methoxycarbonyl, ethoxy carbonyl, i-propoxycarbonyl, n-propoxycarbonyl, allyloxycarbonyl, SCI ^" ,, SCCI ₂ F, SOCF ,, SOCCl ₂ F, SO ₂ CF \,

SO ₂ CCI, F, SCHF ₂ , SOCHF ,, SO ₂ CHF ₂ or CSNH ₂ ,

IV for hydrogen, methyl, ethyl, n- or i-propyl, methoxymethyl,

Ethoxymethyl, n-propoxymethyl, n-butoxymethyl; Methylcarbonyl,

Methylsulfonyl; each phenylcarbonyl or benzyl, optionally substituted once or twice, identically or differently by fluorine, chlorine, methyl or trifluoromethyl; or cyclopropyl,

R ⁴ represents optionally mono- to trisubstituted by identical or different substituents, suitable substituents being halogen, nitro, cyano, C _j ^ -C alkyl, C, -C ₁₂ -halogenoalkyl having 1 to 5 identical or different halogen atoms, such as fluorine - and chlorine atoms, C, - C ₄ alkoxy, C _] -C ₄ haloalkoxy with 1 to 5 identical or different halogen atoms, such as fluorine and chlorine atoms, C- -C ₄ alkylthio, C ₁ -C ₄ - Haloalkylthio with 1 to 5 identical or different halogen atoms, such as fluorine and chlorine atoms, C -, - C ₄ alkenyl,

C, -C ₄ -Halogenalkenyl with 1 to 5 identical or different halogen atoms, such as fluorine and chlorine atoms and each optionally one to three times, the same or different, by halogen, nitro, cyano, C ₁ -C ₄ alkyl, C _] -C ₄ -haloalkyl with 1 to 5 identical or different halogen atoms, such as fluorine and chlorine atoms, C--

C -alkoxy, C, -C ₄ -haloalkoxy with 1 to 5 identical or different halogen atoms, such as fluorine and chlorine atoms, C, -C - Alkylthio, C, -C ₄ -haloalkylthio with 1 to 5 identical or different halogen atoms, such as fluorine or chlorine atoms, C - C ₄ - alkylthio-C, -C ₄ -alkyl, C, -C ₄ -alkylsulfonyI, C, -C ₄ -Halogenalkylsul- fonyl with 1 to 5 identical or different halogen atoms, such as fluorine or chlorine atoms, C _[ -C ₄ alkylcarbonyl, C ^ _j -alkoxy-carbonyl, thiocarbamoyl, C, -C ₄ - Alkoximino-C ₁ -C -, - or optionally substituted by C Cτalkyl 1, 2,4-oxdiazolyl-3-yl substituted phenoxy, phenylthio or benzyloxy and

Y one of the Gaippen

-CII ₂ -, -CH (CH.) -. -CH (C ₂ H ₅ ) -, -CH (nC, H ₇ ) -, -CH (iC ₃ H ₇ ) -, -CI I ₂ CI I ₂ -, -CH (OH) -, -CH (OCH ,) -, -CH (O-CO-CH,) -, -CH (CN) -,

-CHF-, -CHC1-, -CH -R] -CH = CH- or -CH, 0-

where the left side of the group is linked to the thiocarbonyl group

Compounds of formula (I) according to claim 1, in which

R ^{1 represents} methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, CH ₂ F, CHF ₂ , CF ,, CH ₂ C1, CH ₂ Br, methoxy or ethoxy,

R ^{: represents} hydrogen, chlorine, bromine, cyano, nitro, thiocyanato, methoxycarbonyl or ethoxycarbonyl,

R ^{1 represents} hydrogen, methyl, ethyl, methoxymethyl, ethoxymethyl, methylcarbonyl, phenylcarbonyl or methylsulfonyl,

R ⁴ for phenyl which is monosubstituted to trisubstituted by identical or different substituents, fluorine, chlorine, bromine, nitro, cyano, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl as substituents ,

Methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methylthio, CF ₃ , OCF ₃ , OCHF ₂ , SCF ₃ , SCC1 ₂ F, CH ₂ Br, CH ₂ CI and 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, CF ₃ . OCF ^, OCHF ₂ , SCF ₃ , SCC1 ₂ F, CH ₂ Br, CH ₂ C1, acetyl, ethylcarbonyl, methoxycarbonyl, methylsulfonyl, trifluoromethylsulfonyl. Thio-carbamoyl, methoximinomethyl, l - (methoximino) ethyl, l - (ethoximino) ethyl, l, 2,4-oxdiazol-3-yl or 5-methyl-l, 2,4-oxdiazol-3-yl substituted Phenoxy come into question and

Y represents -CH ₂ - or -CH (CH ₃ ) -.

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

R ¹ , R "and R ' ^{1 have} the meaning given in claim 1,

a) with compounds of the formula (III)

R ⁴ -Y-CS-G (III)

in which

R ⁴ and Y have the meaning given in claim 1 and

G represents a leaving group,

or b) with dithioesters of the formula (IV)

Alk-S-CS-YR ⁴ (IV)

in which

R ⁴ and Y have the meaning given in Claim I and

Alk represents alkyl or CH ₂ COOM, where

M represents an alkali metal,

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

R 1, D R2 ^~ , R _D 3 ^~ , D R4 and Y have the meaning given in claim 1,

with a sulfurizing agent, if appropriate in the presence of a diluent.

6 pesticides, characterized by a content of at least one compound of the formula (I) according to claim 1 Use of compounds of formula (I) according to claim 1 for controlling pests

Process for combating pests, characterized in that compounds of the formula (I) according to Claim 1 are allowed to act on pests and / or their habitat

Process for the preparation of pesticides, characterized in that compounds of the formula (I) according to Claim 1 are mixed with extenders and / or surface-active agents

Use of compounds of formula (I) according to claim 1 for the manufacture of pesticides