HK1021533A - Substituted n-(5-isothiazolyl)-thioamides - Google Patents

Description

Substituted N- (5-isothiazolyl) -thioamides

The invention relates to novel substituted N- (5-isothiazolyl) -thioamides, to a method for the production thereof and to the use thereof for controlling animal pests.

It is known that certain N- (5-isothiazolyl) -amides have insecticidal properties (see, for example, WO-95/31448 and DE-A-19542372).

However, the efficacy and activity spectrum of these compounds, especially at low application rates and concentrations, are not entirely satisfactory.

Accordingly, the present invention provides novel substituted N- (5-isothiazolyl) -thioamides of formula (I)Wherein R is¹Represents alkyl, haloalkyl, alkoxyalkyl, alkylthioalkyl, alkoxy, alkylthio or optionally substituted cycloalkyl, R²Represents hydrogen, halogen, cyano, nitro, thiocyanato, alkoxycarbonyl, alkenyloxycarbonyl, alkylthio, haloalkylthio, alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, haloalkylsulfonyl or thiocarbamoyl, R³Represents hydrogen, alkyl, haloalkyl, alkoxyalkyl, alkylcarbonyl, alkylsulfonyl, represents arylcarbonyl, arylsulfonyl or arylalkyl, each of which is optionally substituted, or represents optionally substituted cycloalkyl, R⁴Represents optionally substituted aryl, optionally substituted cycloalkyl or optionally substituted cycloalkenyl, and Y represents optionally substituted alkylene, alkenylene or alkyleneoxy.

Furthermore, it has been found that compounds of the formula (I) A) compounds of the formula (II) are obtainedWherein R is¹、R²And R³Each as defined above a) with a compound of formula (III),

R⁴-Y-CS-G (Ⅲ)

wherein

R⁴And Y are each as defined above, and

g represents a leaving group, for example halogen (in particular chlorine), imidazolyl, benzimidazolyl, 1,2, 4-triazolyl, pyrazolyl or benzotriazolyl,

or b) reaction with dithioesters of the formula (IV)

Alk-S-CS-Y-R⁴ (Ⅳ)

Wherein

R⁴And Y are each as defined above, and

alk represents alkyl (e.g., methyl or ethyl) or CH₂COOM, wherein

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)

Wherein

R¹、R²、R³、R⁴And Y are each as defined above, and,

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

Finally, it has been found that the novel compounds of the formula (I) have outstanding biological properties and are outstandingly suitable for controlling animal pests, in particular insects, acarids and nematodes which occur in agriculture, in forests, in the protection of stored goods and materials and in hygiene.

Surprisingly, the substituted N- (5-isothiazolyl) -thioamides according to the invention have a much better activity against animal pests than the known compounds of similar structure.

Formula (I) provides a general definition of the compounds of the invention.

The ranges of preferred substituents or groups listed in the formulae provided above and below are specified below. R¹Preferably represents C₁-C₄Alkyl, C having 1 to 5 identical or different halogen atoms, such as fluorine, chlorine and bromine atoms₁-C₄-haloalkyl group, C₁-C₄-alkoxy-C₁-C₄Alkyl radical, C₁-C₄-alkylthio-C₁-C₄Alkyl radical, C₁-C₄-alkoxy, C₁-C₄-alkylthio, or represents optionally substituted by a group selected from C₁-C₄C mono-to trisubstituted by the same or different substituents of alkyl and halogen₃-C₆-a cycloalkyl group. R²Preferably represents hydrogen, halogen, cyano, nitro, thiocyanato, C₁-C₄Alkoxycarbonyl, C₂-C₄-alkenyloxy-carbonyl, C₁-C₄Alkylthio, C having 1 to 5 identical or different halogen atoms, such as fluorine and chlorine atoms₁-C₄-haloalkylthio, C₁-C₄-alkylsulfinyl, C having 1 to 5 identical or different halogen atoms, such as fluorine and chlorine atoms₁-C₄-haloalkylsulfinyl, C₁-C₄Alkylsulfonyl, C having 1 to 5 identical or different halogen atoms, e.g. fluorine and chlorine atoms₁-C₄-haloalkylsulfonyl or represents thiocarbamoyl. R³Preferably represents hydrogen, C₁-C₄Alkyl, C having 1 to 5 identical or different halogen atoms, such as fluorine and chlorine atoms₁-C₄-haloalkyl group, C₁-C₄-alkoxy-C₁-C₄Alkyl radical, C₁-C₄-alkyl-carbonyl, C₁-C₄Alkylsulfonyl, represents phenylcarbonyl, phenylsulfonyl or benzyl, each of which is optionally mono-to trisubstituted on the phenyl ring by identical or different substituents, the possible substituents being in each case halogen, nitro, cyano, C₁-C₄Alkyl, C having 1 to 5 identical or different halogen atoms, such as fluorine and chlorine atoms₁-C₂-haloalkyl group, C₁-C₄-alkoxy, C₁-C₄Alkylthio, C having 1 to 5 identical or different halogen atoms, such as fluorine and chlorine atoms₁-C₂Haloalkoxy or C having 1 to 5 identical or different halogen atoms, such as fluorine and chlorine atoms₁-C₂-haloalkylthio, or represents optionally substituted by a group selected from C₁-C₄C mono-to trisubstituted by the same or different substituents of alkyl and halogen₃-C₆-a cycloalkyl group. R⁴Preferably represents phenyl, which is optionally mono-to trisubstituted by identical or different substituents, possible substituents being halogen, nitro, cyano, C₁-C₁₂Alkyl, C having 1 to 5 identical or different halogen atoms, such as fluorine and chlorine atoms₁-C₁₂-haloalkyl group, C₁-C₁₂Alkoxy, C having 1 to 5 identical or different halogen atoms, such as fluorine and chlorine atoms₁-C₁₂-haloalkoxy, C₁-C₁₂Alkylthio, C having 1 to 5 identical or different halogen atoms, such as fluorine and chlorine atoms₁-C₁₂-haloalkylthio, C₂-C₁₂Alkenyl, C having 1 to 5 identical or different halogen atoms, e.g. fluorine and chlorine atoms₂-C₁₂-haloalkenyl, optionally substituted by a group selected from C₁-C₄C mono-to trisubstituted by the same or different substituents of alkyl and halogen₃-C₈-cycloalkyl, and phenyl, phenoxy, phenylthio, benzyl or benzyloxy, each of which is optionally mono-to trisubstituted, in particular in the phenyl moiety, by identical or different substituents selected from the group consisting of: halogen, nitro, cyano, C₁-C₄Alkyl, C having 1 to 5 identical or different halogen atoms, such as fluorine and chlorine atoms₁-C₄-haloalkyl group, C₁-C₄Alkoxy, C having 1 to 5 identical or different halogen atoms, such as fluorine and chlorine atoms₁-C₄-haloalkoxy, C₁-C₄Alkylthio, C having 1 to 5 identical or different halogen atoms, such as fluorine and chlorine atoms₁-C₄-haloalkylthio, C₁-C₄-alkylthio-C₁-C₄Alkyl radical, C₁-C₄-alkylsulfonyl, having 1 to 5, identical or differentWith halogen atoms, e.g. fluorine and chlorine atoms C₁-C₄-haloalkylsulfonyl, C₁-C₄-alkylcarbonyl group, C₁-C₄Alkoxycarbonyl, thiocarbamoyl, C₁-C₄-alkoxyimino-C₁-C₄-alkyl and optionally C₁-C₄-an alkyl-substituted oxadiazolyl group, or represents C₃-C₈-cycloalkyl or C₅-C₈Cycloalkenyl, each of which is optionally mono-to trisubstituted by identical or different substituents, possible substituents being: c₁-C₄Alkyl, C having 1 to 5 identical or different halogen atoms, such as fluorine and chlorine atoms₁-C₄-haloalkyl group, C₁-C₄Alkoxy, C having 1 to 5 identical or different halogen atoms, such as fluorine and chlorine atoms₁-C₄-haloalkoxy, C₃-C₈-cycloalkyl, and phenyl, the phenyl being optionally mono-to trisubstituted by identical or different substituents selected from the group consisting of: halogen, cyano, nitro, C₁-C₄Alkyl, C having 1 to 5 identical or different halogen atoms, such as fluorine and chlorine atoms₁-C₄-haloalkyl group, C₁-C₄Alkoxy and C having 1 to 5 identical or different halogen atoms, e.g. fluorine and chlorine atoms₁-C₄-haloalkoxy. Y preferably represents C₁-C₆Alkylene radical, C₁-C₆Hydroxy alkylene, C₁-C₄-alkoxy-C₁-C₆Alkylene radical, C₁-C₄-alkylcarbonyloxy-C₁-C₆Alkylene, cyano-C₁-C₆Alkylene, C having 1 to 5 identical or different halogen atoms, e.g. fluorine and chlorine atoms₁-C₄-a haloalkylene group; c₁-C₄Alkylene oxide radical, C₂-C₄-alkenylene or C₃-C₆-cycloalkyl-C₁-C₄Alkylene, which is optionally mono-to trisubstituted by identical or different substituents from the group consisting of fluorine, chlorine and methyl. R¹Particularly preferably represents methyl, ethyl, n-or i-propyl, n-, i-, s-or t-butyl; CH (CH)₂F、CHF₂、CF₃、CH₂Cl、CH₂Br、CRClCH₃(ii) a Methoxy, ethoxy, methoxymethyl, ethoxymethyl; methylthiomethyl or cyclopropyl. R²Particularly preferably represents hydrogen, chlorine, bromine, cyano, nitro, thiocyanato; methoxycarbonyl, ethoxycarbonyl, isopropoxycarbonyl, n-propoxycarbonyl; allyloxycarbonyl; SCF₃、SCCl₂F、SOCF₃、SOCCl₂F、SO₂CF₃、SO₂CCl₂F、SCHF₂、SOCHF₂、SO₂CHF₂Or CSNH₂。R³Particularly preferably represents hydrogen, methyl, ethyl, n-or i-propyl; methoxymethyl, ethoxymethyl, n-propoxymethyl, n-butoxymethyl; methylcarbonyl, methylsulfonyl; phenylcarbonyl or benzyl, both of which are optionally mono-or disubstituted by identical or different substituents from the group consisting of fluorine, chlorine, methyl and trifluoromethyl; or a cyclopropyl group. R⁴Particularly preferably represents phenyl which is optionally mono-to trisubstituted by identical or different substituents, possible substituents being halogen, nitro, cyano, C₁-C₁₂Alkyl, C having 1 to 5 identical or different halogen atoms, such as fluorine and chlorine atoms₁-C₁₂-haloalkyl group, C₁-C₄Alkoxy, C having 1 to 5 identical or different halogen atoms, such as fluorine and chlorine atoms₁-C₄-haloalkoxy, C₁-C₄Alkylthio, C having 1 to 5 identical or different halogen atoms, such as fluorine and chlorine atoms₁-C₄-haloalkylthio, C₂-C₄Alkenyl, C having 1 to 5 identical or different halogen atoms, e.g. fluorine and chlorine atoms₂-C₄-haloalkenyl, and phenoxy, phenylthio or benzyloxy, the latter three being each optionally mono-to trisubstituted by identical or different substituents selected from the group consisting of: halogen, nitro, cyano, C₁-C₄Alkyl, C having 1 to 5 identical or different halogen atoms, such as fluorine and chlorine atoms₁-C₄-haloalkyl group, C₁-C₄Alkoxy, C having 1 to 5 identical or different halogen atoms, such as fluorine and chlorine atoms₁-C₄-haloAlkoxy radical, C₁-C₄Alkylthio, C having 1 to 5 identical or different halogen atoms, such as fluorine and chlorine atoms₁-C₄-haloalkylthio, C₁-C₄-alkylthio-C₁-C₄Alkyl radical, C₁-C₄Alkylsulfonyl, C having 1 to 5 identical or different halogen atoms, e.g. fluorine and chlorine atoms₁-C₄-haloalkylsulfonyl, C₁-C₄-alkylcarbonyl group, C₁-C₄Alkoxycarbonyl, thiocarbamoyl, C₁-C₄-alkoxyimino-C₁-C₂-alkyl and optionally C₁-C₂-alkyl substituted 1,2, 4-oxadiazol-3-yl. Y particularly preferably represents one of the following groups: -CH₂-,-CH(CH₃)-,-CH(C₂H₅)-,-CH(n-C₃H₇)-,-CH(i-C₃H₇)-,-CH₂CH₂-,-CH(OH)-,-CH(OCH₃)-,-CH(O-CO-CH₃)-,-CH(CN)-,-CHF-,-CHCl-,CH = CH-or-CH₂O-，

Wherein in each case the group is attached to the thiocarbonyl group on the left. R¹Very particularly preferably represents methyl, ethyl, n-or i-propyl, n-, i-, s-or t-butyl; CH (CH)₂F、CHF₂、CF₃、CH₂Cl、CH₂Br, methoxy or ethoxy. R²Very particularly preferably represents hydrogen, chlorine, bromine, cyano, nitro, thiocyanato, methoxycarbonyl or ethoxycarbonyl. R³Very particularly preferably represents hydrogen, methyl, ethyl, methoxymethyl, ethoxymethyl, methylcarbonyl, phenylcarbonyl or methylsulfonyl. R⁴Very particularly preferably represents phenyl, which is optionally mono-to trisubstituted by identical or different substituents, possible substituents being fluorine, chlorine, bromine, nitro, cyano, methyl, ethyl, n-or i-propyl, n-, i-, s-or t-butyl; methoxy, ethoxy, n-or isopropoxy, n-, iso-, sec-or tert-butoxy; methylthio radical, CF₃、OCF₃、OCHF₂、SCF₃、SCCl₂F、CH₂Br、CH₂Cl, and a phenoxy group, the phenoxy group being optionally mono-to trisubstituted by the same or different substituents selected from the group consisting of: 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, thiocarbamoyl, methoxyiminomethyl, 1- (methoxyimino) ethyl, 1- (ethoxyimino) ethyl, 1,2, 4-oxadiazol-3-yl or 5-methyl-1, 2, 4-oxadiazol-3-yl. Y very particularly preferably represents-CH₂-or-CH (CH)₃)-。

Preferred compounds of the invention are substances of the formula (IA) or (IB):wherein R is¹、R²And R³Have the abovementioned general, preferred, particularly preferred and very particularly preferred meanings, and X¹、X²、X³、X⁴And X⁵Represents as hereinbefore defined in R⁴The substituents mentioned for the phenyl and/or phenoxy radicals in general, preferably, particularly preferably and very particularly preferably, and X¹、X²、X³And X⁴And in each case also represents hydrogen.

Another group of preferred compounds are those of formula (IA) or (IB) wherein phenoxy is at NR³-CS-CH₂-or NR³-CS-CH(CH₃) Para to the radical, and among these compounds, particular preference is given to those in which the substituent X is¹、X²、X³And X⁴A compound representing hydrogen.

The general or preferred radical definitions and explanations mentioned above apply to the end products and likewise to the starting materials and intermediates. These radical definitions may be combined with one another as desired, i.e., also between the respective preferred ranges.

Preferred according to the invention are those compounds of formula (I) which exhibit a combination of the preferred meanings given above.

Particularly preferred according to the invention are those compounds of the formula (I) which exhibit a combination of the meanings given above as being particularly preferred.

Very particular preference according to the invention is given to those compounds of the formula (I) which exhibit a combination of the meanings given above as being very particularly preferred.

In the definitions of the groups given below, the hydrocarbon radicals such as alkyl or alkenyl, including in combination with heteroatoms such as alkoxy or alkylthio, may each be straight-chain or branched as desired.

In addition to the preparation examples, mention may be made in particular of the following compounds of formula (IC):

TABLE A

R1	R2	R3	Y	X
					C2H5C2H5C2H5C2H5C2H5C2H5C2H5C2H5C2H5C2H5C2H5C2H5C2H5C2H5	ClClClClClClClClClClClClClCl	HHHHHHHHHHHHHH	CH2CH2CH2CH2CH2CH2CH2CH2CH2CHCH3CHCH3CHCH3CHCH3CHCH3	4-NO24-Cl4-OCF34-CF34-SCF34-SCH34-SO2CH34-SO2CF34-CO2CH34-CN4-NO24-Cl4-OCF34-CF3

R1	R2	R3	Y	X
					C2H5C2H5C2H5C2H 5C2H5C2H5C2H5C2H5C2H5C2H5C2H5C2H5C2H5C2H5C2H5C2H5C2H5C2H5C2H5C2H5C2H5C2H5C2H5C2H5C2H5C2H5C2H5C2H5C2H5	ClClClClClClClClClClClClClBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBr	HHHHHHHHCH3CH3CH3CH3COCH3HHHHHHHHHHHHHHCH3CH3	CHCH3CHCH3CHCH3CHCH3CHCH3CH2CH2CHCHCH2OCH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CHCH3CH2CH2CHCHCH2OCH2CH2	4-SCF34-SCH34-SO2CH34-SO2CF34-CO2CH34-CN4-CN4-CN4-CN4-NO24-OCF34-Cl4-CN4-CN4-NO24-Cl4-OCF34-CF34-SCF34-SCH34-SO2CH34-SO2CF34-CO2CH34-CN4-CN4-CN4-CN4-CN4-NO2

R1	R2	R3	Y	X
					C2H5C2H5C2H5C2H5C2H5C2H5C2H5C2H5C2H5C2H5C2H5C2H5CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3	BrBrBrNO2NO2NO2NO2NO2NO2NO2NO2NO2CO2EtCO2EtCO2EtCO2EtClCO2EtCO2EtCO2EtCO2EtCO2EtCO2EtCO2EtCO2EtCO2EtCO2MeCO2MeCO2Me	CH3CH3COCH3HHHHHHHHHHHHHHHHHHHHHHHHHH	CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CHCHCH2OCH2CH2CH2	4-OCF34-Cl4-CN4-CN4-NO24-Cl4-OCF34-CF34-SCF34-SCH34-SO2CH34-SO2CF34-CN4-NO24-Cl4-OCF34-CN4-CF34-SCF34-SCH34-SO2CH34-SO2CF34-CO2CH34-CN4-CN4-CN4-CN4-NO24-Cl

R1	R2	R3	Y	X
					CH3CH3C2H5C2H5C2H5C2H5C2H5C2H5C2H5C2H5C2H5C2H5C2H5C2H5C2H5C2H5C2H5C2H5C2H5C2H5C2H5C2H5C2H5C2H5C2H5C2H5CH3CH3CH3	CO2MeCO2MeCO2MeCO2MeCO2MeCO2MeCO2MeCNCNCNCNCNCNCNCNCNCNCSNH2CSNH2CSNH2CSNH2CSNH2CSNH2CSNH2CSNH2CSNH2SCNSCNSCN	HHHHHHHHHHHHHHHHHHHHHHHHHHHHH	CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CHCHCH2OCH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2	4-OCF34-CF34-CN4-NO24-Cl4-OCF34-CF34-NO24-Cl4-CF34-SCF34-SO2CH34-SO2CF34-CO2CH34-CN4-CN4-CN4-CN4-NO24-Cl4-OCF34-CF34-SCF34-SCH34-SO2CH34-SO2CF34-CN4-NO24-Cl

R1	R2	R3	Y	X
					CH3CH3CH3CH3CH3CH3OC2H5OC2H5OC2H5OC2H5	SCNSCNSCNSCNSCNSCNCO2EtCO2EtCO2EtCO2Et	HHHHHHHHHH	CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2	4-OCF34-CF34-SCF34-SCH34-SO2CH34-SO2CF34-CN4-NO24-Cl4-OCF3

According to process (Aa), using, for example, 5-amino-4-chloro-3-ethylisothiazole and 4- (4-cyanophenoxy) -phenylthioacetyl chloride as starting materials, the process of the invention can be represented by the following reaction scheme:

according to process (Ab), using, for example, 5-amino-4-chloro-3-ethylisothiazole and 4- (4-chlorophenoxy) -phenyl-dithioacetic acid methyl ester as starting materials, the process of the invention can be represented by the following reaction scheme:

according to process (B), using, for example, N- (4-chloro-3-ethyl-5-thiazolyl) -4- (4-cyanophenoxy) -phenylacetamide as starting material and Lawesson's reagent (2, 4-bis- (4-methoxyphenyl) -1, 3-dithia-2, 4-diphospha-2, 4-disulfide as sulfurizing agent, the route of the process of the invention can be represented by the following reaction scheme:

the majority of 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 known (see, for example, the patent applications cited at the outset), or they can be prepared by the processes described therein.

The compounds of the formula (III) which are additionally required as starting materials in the process (Aa) according to the invention are generally known organic chemical compounds. In formula (III), G preferably represents imidazolyl (see, for example, Lepishi chem. note [ Liebigs an. chem. ]739,201 (1970)).

The formula (IV) provides a general definition of the dithioesters which are additionally required as starting materials for carrying out the process (Ab) according to the invention. In this formula (IV), Alk preferably represents methyl or CH₂COONa。

Dithioesters of the formula (IV) are known (see, for example, Tetrahedron 2663(1984), J.chem.Research (M)2701(1988), chemical industry (chem.Ind.) (London) 803, 1974, Russian chemical Commission (Russ.chem.Rev.) ]45,1035(1976) and/or they can be prepared by known analogous methods.

The compounds of the formula (V) required for carrying out process (B) according to the invention are known from the patent applications cited at the outset, or they can be prepared by the processes described therein.

The preferred sulfurizing agents for carrying out process (B) according to the invention are phosphorus pentasulfide or Lawesson's reagent [2, 4-bis- (4-methoxyphenyl) -1, 3-dithia-2, 4-diphospha-2, 4-disulfide ] (see Tetrahedron [ Tetrahedron ] Vol.41, p.22, p.5061 et al (1985) ].

The process (Aa) described above for the preparation of compounds of formula (I) is carried out in the presence of a diluent. Suitable diluents are all customary solvents.

Preference is given to using optionally halogenated aliphatic or aromatic hydrocarbons, ethers or nitriles, such as cyclohexane, toluene, chlorobenzene, chloroform, dichloromethane, dichloroethane, dioxane, tetrahydrofuran, diethyl ether or acetonitrile.

The process (Aa) described above for preparing the compounds of formula (I) is carried out in the presence of a base (see, for example, chemical bulletin [ chem. Ber. ]98,829 (1965); Liebigs Ann. chem. ]739,201(1970) and 636 (1973)).

Suitable bases for the process (Aa) are all customary proton acceptors. Preference is given to using alkali metal or alkaline earth metal hydroxides, alkali metal or alkaline earth metal carbonates or bicarbonates or nitrogenous bases. Examples include sodium hydroxide, calcium hydroxide, potassium carbonate, sodium bicarbonate, triethylamine, dibenzylamine, diisopropylamine, pyridine, quinoline, Diazabicyclooctane (DABCO), Diazabicyclononene (DBN), and Diazabicycloundecene (DBU).

In the process (Aa), the reaction temperature may be varied within a relatively wide range. Generally, the reaction is carried out at a temperature of-40 ℃ to +200 ℃, preferably between 0 ℃ and 100 ℃.

When carrying out the process (Aa) for preparing the compound of the formula (I) described above, usually 1 to 2 moles, preferably 1 to 1.5 moles of the compound of the formula (III) are employed per mole of the 5-aminoisothiazole of the formula (II).

In some cases, it is advantageous here to use the hydrohalide salt form, such as, in particular, the hydrochloride, of the 5-aminoisothiazole of the formula (II).

The work-up and isolation of the end product is carried out in a manner known per se.

Suitable diluents for carrying out the process (Ab) according to the invention are all customary solvents. Preference is given to using optionally halogenated aliphatic or aromatic hydrocarbons, such as methylene chloride, dichloroethane, cyclohexane, toluene or chlorobenzene.

However, the process can also be carried out without solvent, undiluted.

When carrying out the process (Ab) according to the invention, the reaction temperature can be varied within a relatively wide range. Generally, the process is carried out at a temperature of between 0 ℃ and 150 ℃, preferably between 20 ℃ and 120 ℃.

When carrying out the process (Ab) according to the invention, in general from 1 to 3 mol, preferably from 1 to 1.5 mol, of dithioester of the formula (IV) are employed per mole of pyridylamine of the formula (III). The work-up is carried out by conventional methods.

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

When carrying out the process (B) according to the invention, the reaction temperatures can be varied within a relatively wide range. Generally, the process is carried out at a temperature of from 0 ℃ to 200 ℃, preferably between 20 ℃ and 150 ℃.

When carrying out process (A) according to the invention, from 1 to 3 mol, preferably from 1 to 2 mol, of sulfiding agent are generally employed per mole of compound of the formula (II). The work-up is carried out by conventional methods.

The compounds of formula (i) can also be obtained as follows:

reacting a 5-isothiazolyl isothiocyanate of formula (VI) with a Grignard reagent of formula (VII)Wherein R is¹And 2^REach as defined above

Hal’-Mg-Y-R⁴(VII) in which Hal' represents halogen, in particular chlorine or bromine, and Y and R⁴The reaction is carried out in a conventional manner, each as defined above (in this connection, see JACS4849 (1955)). N- (5-isothiazolyl) -thioamides of formula (Ia)Wherein

R¹、R²、R³And R⁴Each as defined above may also be obtained as follows: reacting a 5-aminoisothiazole of formula (III) with a carbonyl compound of formula (VIII) in the presence of sulphur,wherein R is¹、R²And R³Each as defined above

E-CO-CH₂-R⁴(VIII) wherein E represents hydrogen or methyl, and R⁴As defined above, (see, e.g., pet. chem. ussr (engl. trans.) 345(1993)) in this regard.

If appropriate, the substituted N- (5-isothiazolyl) -thioamides of the formula (I) according to the invention can be converted in a known manner into their corresponding N-oxides or their salt derivatives; they also form the subject of the present application.

The active compounds according to the invention have good plant tolerance and low toxicity to warm-blooded animals and are suitable for controlling animal pests, in particular insects, acarids and nematodes, which occur in agriculture, in forests, in the protection of stored products and of materials and in hygiene. They can preferably be used as plant protection agents. They are active against normally sensitive and resistant species and against all or some stages of growth and development. The pests include:

isopoda, for example, Oniscus asellus, Armadillidium vulgare and Armadillidium maculatum (Porcellio scaber).

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

From the order of the Chilopoda, for example, Geophilus carpopophagus (Geophilus carpopophagus) and Scutigera spp (Scutigera spec).

The order of the Symphyla, for example, Scutigerella immaculata (Scutigerella immaculata).

From the order of the Thysanura, for example, Lepisma saccharina (Lepisma saccharana).

From the order of the Collembola, for example, Onychiurus armatus (Onychiurus armatus).

From the order of the orthoptera, for example, Blatta orientalis (Blatta orientalis), Blatta americana (Periplaneta americana), Blatta maderae (Leucophaea maderae), Blattella germanica (Blattaella germanica), Acheta domestica (Achatta domisticus), Gryllotalpa spp., locustaria migratoria (locustata migratoria), Trichosta trifoliata (Melanophaga differarioides), and Trichosta rostrata (Schocisterculia gigas).

From the order of the Dermaptera, for example, Forficula auricularia (Forficula auricularia).

From the order of the Isoptera, for example, the genus Rhinoceros (Reticulitermes spp.).

From the order of the Anoplura, for example, the Pediculus humanus (Pediculus humanus murroris), the genus Haematopinus (Haematopinus spp.) and the genus Chitophagus (Linoganthus spp.).

From the order of the mallophaga, for example, psocida (trichoectes spp.) and zoo (damalina spp.).

From the order of the Thysanoptera, for example, Hercinothrips femoralis (Hercinothrips femoralis) and Thrips gossypii (Thrips tabaci).

From the order of the hemiptera, for example, the genus Acidophytus (Eurygaster spp.), the genus Meadous medicinalis (Dysdercusintermediate), the genus Phryptophytes coriaria (Piesma quadrata), the genus Cimexlestus (Cimexlelectulariatus), the genus Nephophorus longissima (Rhodnius prolixus) and the genus Nephophorus (Triatomaspp).

From the order of the homoptera, for example, cabbage whitefly (Aleurodes brassicae), sweet potato whitefly (Bemis tabaci), greenhouse whitefly (Trialeurodes vaporariorum), cotton aphid (Aphis gossypii), cabbage aphid (Brevicoryne brassicae), Cryptophycus theophyllae (Cryptomyces ribis), beet aphid (Aphis fabae), apple aphid (Aphis pomphoides), apple aphid (Eriosoma lanigerum), peach tail aphid (Hyalopterusundalis), Rhizoctonia Juglandis (Phyllotrex vasstrix), gall bladder aphid (Pemphigus spp.), Phyllophycus elongatus (Macrosiphumus avenae), Phyllophycus nodorum (Phyllophycus), Phyllophycus nigra (Phyllopterocarpa), Sinorhiza virginiana (Phyllocerulosa), Phyllophora nodorhiza virginica (Pholiopsis persica), Phytopsis oryzae (Pholiopsis punctata), Phyllostachydia virginica (Phorbina), Phytopsis nilotica viridis (Nephoma), Phormidis indica (Phormidis) and Neurospora (Neurospora), Phormidis nigra), Phormiana (Neurospora.

From the order of the lepidoptera, for example, the species Chrysopa gossypii (Pentinophora gossypii), Trichoplusia (Bupalus piniarius), Plutella xylostella (Cheimatobia brumata), Plutella xylostella (Lithocolletis blanca), Malva Malaria (Hypomeuta Adellata), Plutella xylostella (Plutella maculipennis), Trichoplusia (Malacoris), Flabella lutea (Euproctis chrysospora), Phanera chrysosporium (Lymantria chrysosporium), Trichoplusia nitida (Lymantria punctata), Trichoplusia nitida (Bucculus terrestris), Phyloides (Phyllanthus citri), Phillidium (Agrimonia), Geotrichum (Agrostis spp.), Philiella sp.incisa (Euxola spp.), Spodoptera (Spodopteria), Spodopteria litura (Spodopteria litura), Spodopteria litura (Spodopteria), Spodopteria litura), Spodopteria (Spodopteria), Spodopteria litura), Spodoptera (Spodopteria litura), Spodoptera (Spodopteria litura), Spodopteria (Spodoptera), Spodoptera (Spodopteria (Sphaerotheca), Spodopteria (Sphaerotheca), Spodoptera (Spodopteria (Sporila), Spodoptera) and Sphaerotheca (Spodoptera) or Spodoptera (Spodopteria (Spodoptera), Sphaerotheca (Spodopteria) and Spodoptera), Spodoptera (Sp, Greater wax moth (Galleria mellonella), cottonmoth (tenella bisseliella), bagel moth (tenea pellionella), brown moth (hofmanophil semisepospermella), yellow flax moth (Cacoecia podana), webworm moth (capuarictoria), spruce pine moth (chlamydoneura fumifera), grape fruit moth (Clysia biguella), long tea leaf moth (hobona magna) and oak green leaf moth (torx viridana).

From the order of the coleoptera, for example, the genera Tolyptera (Anobium punctatum), Rhynchophorus (Rhizophradienica), Bruchidia, Coleus (Acanthoscelides), Dolichos domestica (Hylutulus), Alnus castus (Agrestriales), Buxus purpurea (Solanicaalni), Bulletia niphylla (Leptotarsa decemlineata), Homalus cochleariae (Phaedon cochleariae), Bulletia striped (Diabrotica), Bulletia kawakawakamii (Psyliodera), Bulletia papyrifera (Psychiadiophora), Bulletia meyeri (Epila), Bulletia falcatula (Melothrix), Bulletia falcatus (Melothria), Bulletia papyrifera, Melothria, Pilus spp), Hirteria officinalis (Melothria, Hirteria indica (Melothria), Hirteria, Hippo-A-roseria, Melothria (Melothria, Melothria (Pilus napus), Hibiscus (Melothria, Melothria, Golden spider beetles (niptosaloucus), bare spider beetles (gibbsium psiloides), pseudoglutacoides (tribolium spp.), Tenebrio molitor (Tenebrio molitor), click beetles (Agriotes spp.), click beetles (Conoderus spp.), western pentacrythrimeylostome (meloentha), potato branchionus (amphetalon solstialis), and brown new zealand costalidae (costalyt zealandica).

From the order of the hymenoptera, for example, the genera Ceratopterus (Diprion spp.), Ceratoptera (Hoplocpaspp.), Proteus (Lasius spp.), Proteus (Monorium pharaonis) and Vespa spp.

From the order of the diptera, for example, the genera Aedes (Aedes spp.), Anopheles (Anopheles spp.), Culex (Culex spp.), Drosophila (Drosophila melanogaster), Musca (muscsa spp.), latanidae (Fannia spp.), callimastia rubra (calliphora erythrepha), Drosophila (Lucilia spp.), chrysomyzidae (chrysomyzilla spp.), phlegma (curvularia spp.), phlegma (curerbra spp.), gastrophila (gastrophilips), pediculus (diaphagus spp.), Drosophila (diaphaga spp.), stigmas (scleroderma spp.), lasia (diaphaga spp.), stigmas (scleroderma spp.), pelstis (scleroderma spp.), pelteus (hematophagostoc spp.), and callimastia (calliptera), calliptera (hematophagostomidae), calli (calli spp.), codomyia (hematophagus spp.), pelagina (ostrinia (hematophagus spp.), pellicus (ostreae), calliptera (calliptera), calliptera (ostrea), callitrichia (ostrea spp.), pellicus spp.), and trypanosoma (ostrinia), trypanosoma spp.).

From the order of the Siphonaptera, for example, Xenopsylla cheopis (Xenopsylla cheopis) and Siphonaptera (Ceratophyllus spp.).

From the order of the Arachnoides, for example, the Scorpion maurus and the Black cohosh spider (Latrodectus macrants).

From the order of the Acarina, for example, Dermatophagoides pteronyssinus (Acarus sremoni), Dermatophagoides pteronyssinus (Argassp.), Dermanyssus gallinae (Dermanyssusgallinae), Onychus gallinae (Eriophysalis ribacter), Citrus rusticans (Phyllophora), Bufonis (Boophilus spp.), Rhipicephalus (Rhipicephalus spp.), Oryza (Amblyomma spp.), Peropyrifos (Hyalomma spp.), hard ticks (Ixodes spp.), Prime (Psorophys spp.), Dermatophagoides pterus (Psorophys spp.), Dermatophagoides (Chloropophys spp.), Dermatophagoides pterus (Chlorophytes spp.), Dermatophagoides pterus (Sarcophagoides spp.), Sarcophagoides pterus scabies (Sarcophagoides spp.), Sarcophagus scabies (Sarcophagus spp.), and Tetranychus (Bryophycus spp.).

Plant parasitic nematodes include, for example, Pratylenchus spp, peronospora cubensis (radiculosa), leontopodium nematodes (dimynchus dipsaci), hemiptes (tylenchus semipenetrana), heterodera nematodes (heterodera spp), cyst nematodes (Globodera spp), root knot nematodes (melodogyne spp.), aphelegans (aphelenchoides spp.), longhead nematodes (longidrosis spp.), nematode sword (xiphoma spp.) and trenta root nematodes (trichoderma spp.).

The compounds of the formula (I) according to the invention are distinguished in particular by their high insecticidal and acaricidal activity.

They can be employed with particular success for controlling phytophagous insects, such as, for example, the larvae of the mustard beetle (Phaedon cochlaiae), the caterpillars of the diamondback moth (Plutella maculipennis), the cicada nigra (Nephotettix cincticeps) and the larvae of Spodoptera frugiperda (Spodoptera frugiperda), or for controlling phytophagous mites, such as, for example, the Tetranychus urticae (Tetranychus urticae) in greenhouses.

The active compounds can be converted into the customary formulations, such as solutions, emulsions, wettable powders, suspensions, powders, dusts, pastes, soluble powders, granules, suspoemulsions, natural or synthetic materials impregnated with active compound, and microencapsulations in polymeric substances.

These formulations can be produced in a known manner, for example by mixing the active compounds with extenders (i.e. liquids and/or with solid carriers), optionally with surfactants (i.e. emulsifiers and/or dispersants and/or foam formers).

In the case of water as extender, organic solvents can also be used as cosolvents. As liquid solvents, mainly: aromatic compounds, such as xylene, toluene or alkylnaphthalenes, chlorinated aromatic or chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chloroethenes or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, for example mineral oil fractions, mineral and vegetable oils, alcohols, such as butanol or ethylene glycol and ethers and esters thereof, ketones, such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents, such as dimethylformamide or dimethyl sulfoxide, and water.

Suitable solid carriers are:

for example ammonium salts and ground natural minerals such as kaolin, clay, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, and ground synthetic minerals such as highly disperse silica, alumina and silicates; suitable solid carriers for granules are: for example crushed and fractionated natural minerals such as calcite, marble, pumice, sepiolite and dolomite, as well as synthetic granules of organic and inorganic powders, and granules of organic substances such as: sawdust, coconut shells, corn cobs and tobacco stems; suitable emulsifiers and/or foaming agents are: for example nonionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example alkylaryl polyglycol ethers, alkylsulfonates, alkyl sulfates, arylsulfonates and protein hydrolysates; suitable dispersants are: such as lignin sulfite waste liquor and methyl cellulose.

Binders such as carboxymethylcellulose and natural and synthetic polymers in the form of powders, granules or emulsions, such as gum arabic, polyvinyl alcohol and polyvinyl acetate, and natural phospholipids, such as cephalins and lecithins, and synthetic phospholipids, can be used in the formulations. Other possible additives are mineral and vegetable oils.

It is also possible to use colorants such as inorganic pigments, for example iron oxide, titanium oxide and Prussian blue, and organic dyes, such as alizarin dyes, azo dyes and metal phthalocyanine dyes, and micronutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.

The formulations generally contain from 0.1 to 95% by weight of active compound, preferably from 0.5 to 90%.

The active compounds according to the invention can be present in their commercially available formulations and in the use forms prepared from these formulations, in admixture with other active compounds, for example as follows: insecticides, attractants, sterilants, bactericides, acaricides, nematicides, fungicides, growth regulators or herbicides. Pesticides include, for example, phosphates, carbamates, carboxylates, chlorohydrocarbons, phenylureas, microbially produced materials, and others.

Particularly advantageous mixing partners are, for example, the following:

fungicides:

2-aminobutane, 2-anilino-4-methyl-6-cyclopropyl-pyrimidine; 2 ', 6' -dibromo-2-methyl-4 '-trifluoromethoxy-4' -trifluoromethyl-1, 3-thiazole-5-carboxanilide; 2, 6-dichloro-N- (4-trifluoromethylbenzyl) benzamide; (E) -2-methoxyimino-N-methyl-2- (2-phenoxyphenyl) acetamide; 8-hydroxyquinoline sulfate; (E) -methyl 2- {2- [6- (2-cyano-phenoxy) pyrimidin-4-yloxy ] phenyl } -3-methoxyacrylate; (E) -methyl methoxyimino [ α - (o-tolyloxy) -o-tolyl ] acetate; 2-phenylphenol (OPP), aldimorph, alanine, dichlofluanid, penconazole, benalaxyl, iodocarboxin, benomyl, binapacryl, biphenyl, bitertanol, blasticidin, bromuconazole, butyrim sulfonate, buticat, lime-sulphur, captafol, captan, carbendazim, carboxin, metconazole, chloroneb, chlorothalonil, ethiprole, thiabendazole, cymoxanil, cyproconazole, esteramide, antifungal phenol, benzotriazol, dichlofluanid, diclofluazid, niclofenchloramine, diethofencarb, difenoconazole, methamidol, dimethomorph, diniconazole, dinocap, diphenylamine, pyrazofos, triticonazole, dithianon, dodecgonidine, triadimefon, captan, epoxyconazole, pyrimethamidine, clomazole, diclofen, diclofenbuconazole, fenbuconazole, furazafrin, fenpyrad, fenpropiconazole, chlorfenapyr, triphendroxytin, ferbam, azozone, fluazinam, fludioxonil, fluocinonide, fluquinconazole, fluvalizole, flusulfamide, flutolanil, folpet, fosetyl-aluminium, tetrachlorophthalide, fuberidazole, furalaxyl, fenbam, diguanixin, hexachlorobenzene, hexaconazole, mefenoxaprop, imazalil, imibenconazole, iminoctadine acetate, iprobenfos, iprodione, isoprothiolane, kasugamycin, copper agents (such as copper hydroxide, copper naphthenate, basic copper chloride, copper sulfate, copper oxide, quinolinone and bordeaux mixture), bisexual mixture, mancozeb, maneb, mepanide, mefenoxam, metconazol, sulbencarb, basidiocarb, metiram, tiadinil, thifenpyrad, myclobutanil, thiram, iprodione, flufenarimol, ofuracil, oxfenpyramide, oxamide, pyraflufenpyraclostrobin, pyraoxystrobin, penflufen-5, isoprothiolane, tebuconazole, pyraclofos, tebuconazole, pimaricin, piperidinium, polyoxin, probenazole, prochloraz, dimetachlone, propamocarb, propiconazole, metiram, fenamiphos, pyribenzoxim, pyrimethanil, pyroquilon, quintozene, sulphur and sulphur formulations, tebuconazole, phtalmic acid, tetrachloronitrobenzene, tetraconazole, thiabendazole, thiophanate-methyl, thiram, tolclofos-methyl, tolylfluanid, triadimefon, triadimenol, pyrazosin, tricyclazole, morpholine, triflumizole, triforine, triticonazole, oryzanol, vinclozolin, zineb, ziram.

A bactericide:

gossypol, antifungal phenol, chlordine, thiram, kasugamycin, isothiazolinone, furancarboxylic acid, oxytetracycline, probenazole, streptomycin, phthalein, copper sulfate, and other copper preparations.

Insecticide/acaricide/nematicide:

abamectin, AC303630, acephate, fluthrin, gossypol, aldicarb, alphamethrin, amitraz, avermectin (avermectins), AZ60541, toosendanin, ethoprophos, valthion, azocyclotin, bacillus thuringiensis, bendiocarb, benfuracarb, bensulam, alpha-cyhalothrin, bifenthrin, fenobucarb, bromethrin (brofenprox), bromophos, piribos, buprofezin, butoxycarb, butridone, cadusafos, carbaryl, trithion, carbosulfan, cartap, CGA157419, CGA184699, fenthion, phosphorus oxychloride, fenpropathrin, chlorfenphos, chlorfluazuron, chlorfluthrin, chlorpyrifos, methyl chlorpyrifos, resmethrin, cyhalothrin, clofentezine, fenvalerate, etofenprox, cyfluthrin, cyhalothrin, fenprox, cypermethrin, endospermethrin, endosulfan, endosymin, endosymphakombum, isophorate II, diafenthiuron, dinotefuran, clofenphos, dichlorvos, dicliphos, petalofos, ethion, teflubenzuron, dimethoate, methomyl, dioxathion, disulfoton, edifenphos, emamectin benzoate, esfenprophos, dichlorcarb, ethion, ethofenprox, ethoprophos, etrimfos, fenamiphos, fenazaquin, fenbutathion, fenobucarb, fenoxycarb, fenpropathrin, fenvalerate, fipronil, fluazinam, flucycloxuron, flucythrinate, flufenothrin (flufenprox), fluvalinate, fonofofos, fosthiazate, profenofos, fosthiazate, bromethrin (furfenprox), furametpyr, hexaflumeturon, flucetofos, hexythrinate, hexythroketone, imidacloprid, isoprothiolate, lambda-cyhalothrin, fenofos, isoprothion, fenofos, isoprothion, fenofos, fenoxaprop-p, fenofos-p, feno, Pymetrozine, metofos, fenthion sulfoxide, metaldehyde, chlorfenvinphos, methamidophos, methidathion, methiocarb, methomyl, metolcarb, milbemectin, monocrotophos, moxidectin, naled, NC184, fenamidothion, nitenpyram, omethoate, oxamyl, sulfonethion, isoxathion, parathion, methyl parathion, permethrin, phenthoate, phorate, phosmet, phosphamidon, phoxim, pirimicarb, pirimiphos, profenofos, propamocarb, propoxur, low toxicity sulfur, pomade, pymetrozin, pyrazofos, pyridaphenthion, fenpropathrin, pyrethrin, pyridaben, pyriformifen, pyriproxyfen, quinalphos, RH5992, salithion, flusilafluofen, phos, fenphos, fenpropaphos, hydrazide, fenpyraflufen, tefluthrin, tebufenofos, tefluthrin, tebuthiofos, tefluthrin, tebufenofos, terbufacarb, terbufos, fenprophos, thiafenox, thiodicarb, ketoxycarb, fosetyl methyl, quinclofos, thuringiensis, tetrabromthrin, cyenophos, triazophos, triazuron, trichlorfon, chlorfluazuron, trimethacarb, thiofenthion, dimethylcarb, xylylcarb, YI5301/5302, zetamethrin.

Mixtures with other known active compounds, such as herbicides, or with fertilizers and growth regulators are also possible.

Furthermore, the active compounds according to the invention can be present in their commercially available formulations and in the use forms prepared from these formulations. These formulations may be in admixture with a synergist. Synergists are compounds which increase the activity of the active compound, without the added synergist itself needing to be active.

The content of active compound in the use forms prepared from commercially available preparations can vary within a relatively wide range. The active compound concentration of the use forms can be from 0.0000001 to 95% by weight of active compound, preferably between 0.0001 and 1% by weight.

The compounds are employed in a conventional manner suitable for the form used.

When controlling pests in hygiene and stored products, the active compounds have an excellent residual action on wood and china clay and good stability towards alkali on limed substrates.

The active compounds according to the invention are not only active against plant, hygiene and stored-product pests, but also, in veterinary terms, against animal parasites (ectoparasites) such as hard ticks, soft ticks, mange mites, chiggers, (biting and sucking) flies, parasitic fly larvae, lice, hair lice, feather lice and fleas. These parasites include:

from the order of the Anoplura, for example, the genera Haematopinus spp, Chitophilus (Linogashuspp), Pediculus (Pediculus spp), Phthirius spp and Blastus spp.

The orders mallophaga and ambycrina and the suborder gracilia (ischrocerina), for example, the genera trichodina (Trimenopon spp.), brevicornus (Menopon spp.), fabus (Trinoton spp.), boecius (Bovicola spp.), wernecrola (wernecrosellaspp.), Lepikentron spp., pediculidae (damalina spp.), psocolla (trichectes spp.) and felis (Felicola spp.).

Diptera and Petera, for example, the genera Aedes spp (Aedes spp.), Anopheles spp, Culex spp, Simuliumspp, Euschist, Chrysanthemum spp, phlebotomium spp, Lutzomyia spp, Cumidia spp, Culicoides spp, Hericoides spp, Herculella spp, Tabanus spp, Takaemcomia, Tabanus spp, Haastospora spp, Haastopota, Glostridia spp, Bracteola spp, Haynia spp, Haemophilus spp, and Haemophilus spp Lyssodomys (Oestrus spp.), dermomys (Hypodermaspp.), gastromys (gastrophilius spp.), pediculus (Hippoboca spp.), pediculus (lepotena spp.), and pediculus caprinae (Melophagus spp.).

From the order of the Siphonaptera, for example, Siphonaptera (Pulex spp.), Ctenocephalides (Ctenocephalidesspp.), Xenopsylla spp (Xenopsylla spp.), and Siphonaptera (Ceratophyllusspp.).

Hemiptera, for example, the genus Cimex spp, Triatoma spp, Rhodnius spp and panniculirus spp.

From the order of the Blattaria, for example, Blatta orientalis (Blatta orientalis), Periplaneta americana (Periplaneta americana), Blatta germanica (Blattala germanica) and the genus Brown (Suppella spp.).

Acarina and metapneumosub-orders (Metastigmata) and Aero-sub-orders (mesostigmata), for example, Cryptocaryon rhynchophorus (Argas spp.), Chlorophytus spp (Ornithiomorus spp.), Chlorophytus spp (Otabilus spp.), Iridax spp (Ixodes spp.), Acarina spp (Amblymmastasp), Boophilus spp (Boophilus spp.), Dermacentor spp, Haemaphysalis spp (Haemaphysalis spp.), vitrus (Hyalomma spp.), Rhipicephalus spp.), Dermanyssus spp (Rhynchophorridus spp.), Dermanyssus spp., Ricetotrichum spp., Raillicium spp., and Steorophys spp.

Actinedida (Prostomata) and Dermatophagoides (Aphroda), for example, Asoderma (Acarapis spp.), Acanthopanax (Cheyletelella spp.), Ornithophthora (Ornithophtheiella spp.), Sarcophagus (Myobia spp.), Acanthopanax (Psorergateus spp.), Demodex (Demodex spp.), troma (Trombiculus spp.), Yak (Listorphorus spp.), Plasmodium (Acarus spp.), Buprofenophora (Acarus spp.), Tyrophagus spp.), Primulus (Rhynchophagus spp.), Primulus (Tyrophagus spp.), Primulus (Rhynchophagus spp.), and Bupron (Heterophytes spp.), Hypoderma (Heterophys spp.), Hypoderma (Ptnectorphys spp.), Bupron (Pteophys spp.), and Bupron (Bupron, Bupron (Bupron spos, Bupron (Bupron, Bus (Bupron, Bus.

The active compounds of the formula (I) according to the invention are also suitable for controlling arthropods which infest the following animals: agriculturally productive livestock, such as cattle, sheep, goats, horses, pigs, monkeys, camels, buffalo, rabbits, chickens, turkeys, ducks, geese, bees, other domestic animals, such as dogs, cats, caged birds, fish in water tanks, and so-called laboratory animals, such as hamsters, guinea pigs, rats and mice. When controlling these arthropods, it is intended to reduce death and loss of productivity (meat, milk, wool, skins, eggs, honey, etc.). Thus, the use of the active compounds according to the invention makes it possible to achieve more cost-effective animal husbandry.

The active compounds according to the invention can be employed on the veterinary side in a manner known per se by internal administration, for example in the form of tablets, capsules, drinking water, drenches, granules, pastes, boluses, ingestion, suppositories, by parenteral administration, for example by injection (intramuscular, subcutaneous, intravenous, intraperitoneal and the like), implantation, nasal administration, transdermal administration, for example by bath or dipping, spraying, pouring on, spotting on, brushing, dusting, and with the aid of shaped articles containing the active compound, such as neckloops, ear tags, tail tags, leg bands, halters, marking devices and the like.

When used in livestock, domestic animals, etc., the active compounds of the formula (i) can be used in the form of preparations (e.g. dusts, emulsions, flowable powders) containing 1 to 80% by weight of the active compound, which can be applied directly or after dilution by a factor of 100 to 10000, or they can be used in the form of chemical baths.

Furthermore, it has now been found that the compounds of formula (I) according to the invention have a strong insecticidal action against insects which destroy industrial materials.

Examples and preferred insects are the following, but not limited to:

beetles such as

Domesticated beetles (Hylotupes bajuus), Chlorophorus piposis, Rhaponticus robustus (Anobium punctium), Xestobium ruvalosum, Ptilinusprectins, Dendrobium pertinense, Ernobium mollis, Probiumcarpini, Limnocharus brunneus, African meal (L.africanus), platypodium bark (L.napellus), Lasioderma bark (L.Linris), L.pubescens, Troxylophyceae, Lepidium bark (Minthes rugicolus), bark beetle (Xylorus spelterniformus), Trypoden bark (Apatophyceae), Quercus longus bark (Bothrophyllus), bark beetle (Heterophyllus), and Rhizophyllus longus bark (Heterophyllobacter longus, Heterophyllobromyces longus).

From the order of the Dermaptera, e.g.

Small steel wasp (Sirex juvenus), big tree wasp (Urocerus gigas), U.gigas taignus, U.augur.

Termites, e.g.

Wood termites (Kalotermes flavicolis), cryptotermes branchis (cryptotermes branchis), Heterotermes grisea (heteretres indicicola), Reticulitermes flavipes (Reticulitermes flavipes), R.santonecis, R.lucifugus, Australian termites (Masoters darwiniensis), Zootermopsis vandensis, Coptotermes formosanus (Coptotermes formosanus).

Fish with clothes

Such as chlamydomonas occidentalis (Lepisma sacchara).

Industrial materials are herein understood to be non-living materials such as preferably polymeric materials, glues, adhesive materials, paper and board, leather, wood and derived wood products, and paints.

Wood and wood products are very particularly preferred materials which are protected against attack by insects.

Wood and derived wood products which can be protected with the agent according to the invention or the composition containing it are to be understood as meaning, for example, building timber, timber beams, railroad ties, bridge components, jetties, wooden cars, boxes, containers, utility poles, wooden mine roof timber, wooden doors and windows, plywood, particle board, wood-working products, or wood products commonly used in building or joinery.

The active compounds according to the invention can be used as such, in their concentrates or in customary formulations. The conventional formulations are, for example, wettable powders, granules, solutions, suspensions, emulsions or pastes.

The abovementioned formulations 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 repellent, if desired dehydrating agent and UV stabilizer and if desired colorants and dyes and other processing auxiliaries.

Insecticidal compositions or concentrates for the protection of wood and wood products comprise the active compounds in concentrations of from 0.0001 to 95% by weight, in particular from 0.001 to 60% by weight.

The amount of composition or concentrate employed depends on the type and occurrence of the insect, as well as the medium. The optimum amount used can be determined in each case by means of a series of tests. In general, however, it is sufficient to employ from 0.0001 to 20% by weight, preferably from 0.001 to 10% by weight, of active compound, based on the material to be protected.

The solvents and/or diluents used are organic chemical solvents or solvent mixtures and/or oily organic chemical solvents or solvent mixtures of low volatility and/or polar organic chemical solvents or solvent mixtures and/or water, and if appropriate emulsifiers and/or wetting agents.

Preferably, the organic chemical solvent used is an oily or oily solvent having a volatility greater than 35 and a flash point greater than 30 ℃, preferably greater than 45 ℃. The substances used as such oily or oily solvents are of low volatility and insoluble in water, and suitable are mineral oils or aromatic fractions thereof and solvent mixtures containing mineral oils, preferably white spirit, petroleum and/or alkylbenzenes.

Substances which can advantageously be used are mineral oil having a boiling range of from 170 to 220 ℃, petroleum solvent having a boiling range of from 170 to 220 ℃, lard oil having a boiling range of from 250 to 350 ℃, petroleum or turpentine oil having a boiling range of from 160 to 280 ℃.

In a preferred embodiment, the substances used are liquid aliphatic hydrocarbons having a boiling range of from 180 to 210 ℃ or high-boiling mixtures of aromatic or aliphatic hydrocarbons having a boiling range of from 180 to 220 ℃ and/or pyridine oil and/or monochloronaphthalene, preferably α -monochloronaphthalene.

Low volatility organic oily or oily-like solvents having a volatility greater than 35 and a flash point greater than 30 ℃, preferably greater than 45 ℃, may be partially replaced by high or medium volatility organic chemical solvents, provided that the solvent mixture also has a volatility greater than 35 and a flash point greater than 30 ℃, preferably greater than 45 ℃, and the pesticide/fungicide mixture is soluble or emulsifiable in the solvent mixture.

In a preferred embodiment, part of the organic chemical solvent or solvent mixture or the aliphatic polar organic chemical solvent or solvent mixture is replaced. Substances which are preferably employed are aliphatic organic chemical solvents which contain hydroxyl and/or ester and/or ether groups, such as, for example, glycol ethers, esters and the like.

Organic chemical binders which are used within the scope of the present invention are binding drying oils and/or synthetic resins known per se, which can be diluted with water and/or are soluble, dispersible or emulsifiable in the organic chemical solvents employed, in particular those consisting of, or containing: acrylic resins, vinyl resins, for example polyvinyl acetate, polyester resins, polycondensation or polyaddition resins, polyurethane resins, alkyd resins or modified alkyd resins, phenol resins, hydrocarbon resins, such as indene-coumarone resins, silicone resins, drying vegetable oils and/or drying oils and/or physically drying binders based on natural and/or synthetic resins.

The synthetic resin used as the binder may be used in the form of an emulsion, dispersion or solution. Bitumen or bituminous substances may also be used as a binder substance in an amount of up to 10% by weight. In addition, it is possible to use, in particular, pigments, water repellents, odor inhibitors and inhibitors or corrosion inhibitors and the like.

According to the invention, the composition or concentrate preferably contains at least one alkyd resin or modified alkyd resin and/or a drying vegetable oil as organic chemical binder. Substances which are preferably employed according to the invention are alkyd resins having an oil content of more than 45% by weight, preferably from 50 to 68%.

All or part of the above-mentioned binder may be replaced by a fixing agent (mixture) or a plasticizer (mixture). These additives are intended to prevent volatilization and crystallization or precipitation of the active compound. They preferably replace 0.01 to 30% of the binder (based on 100% of the binder used).

Plasticizers come from substances belonging to the following chemical classes: phthalates, such as dibutyl phthalate, dioctyl phthalate or benzylbutyl phthalate, phosphates, such as tributyl phosphate, adipates, such as di-2-ethylhexyl adipate, stearates, such as butyl stearate or amyl stearate, oleates, such as butyl oleate, glycerol ethers or high molecular weight glycol ethers, glycerol esters and p-toluenesulphonates.

The fixing agents are chemically based on polyvinyl alkyl ethers, such as polyvinyl methyl ether, or ketones, such as benzophenone or ethylenebenzophenone.

Particularly suitable solvents or diluents are also water, if appropriate mixtures of water with one or more of the abovementioned organic chemical solvents or diluents, emulsifiers and dispersants.

Particularly effective wood protection is obtained by means of impregnation processes on an industrial scale, for example vacuum, double vacuum or pressure processes.

If appropriate, the directly usable compositions may comprise one or more further insecticides and, if appropriate, also one or more fungicides.

Further suitable components which may be mixed therein are preferably insecticides and fungicides as mentioned in WO 94/29268. The compounds mentioned in the above-mentioned documents are specifically part of the present application.

Components which can very particularly preferably be mixed in are insecticides such as chlorpyrifos, phoxim, silafluofen, cyfluthrin, alphamethrin, cypermethrin, deltamethrin, permethrin, imidacloprid, acetamiprid, flufenoxuron, hexaflumuron and chlorsulfuron, and also fungicides such as epoxiconazole (epoxiconazole), hexaconazole, pentitol, propiconazole, tebuconazole, cyproconazole, metconazol, imazalil, benflumethamine, tolylfluanid, 3-iodo-2-propynylbutylcarbamate, N-octyl-isothiazolin-3-one and 4, 5-dichloro-N-octyl-isothiazolin-3-one.

The preparation and use of the active compounds according to the invention can be illustrated by the following examples.

Preparation examples

Example 1

(method B)

0.50g (1.25mol) N- (3-ethyl-4-chloro-isothiazolyl) -4- (4-cyanophenoxy) -phenyl-acetamide and 0.97g (3.26mmol) Lawesson's reagent were heated under reflux in 20ml toluene for 7 h, and the mixture was concentrated, and the crude product was purified by column chromatography on silica gel (mobile phase: dichloromethane).

This gives 0.16g (31% of theory) of N- (3-ethyl-4-chloro-isothiazolyl) -4- (4-cyanophenoxy) -phenylthioacetamide.

Melting point 177-.

Application examples

Example A

Horseradish Simian Bronyard (Phaedon larvae) assay

Solvent: 7 parts by weight of dimethylformamide

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To prepare a suitable preparation of active compound, one part by weight of active compound is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration.

Cabbage (Brassica oleracea) leaves are treated by immersion in the preparation of active compound of the desired concentration, and, while the leaves are still moist, larvae of the mustard beetle (phaedoncochleriae).

After a certain time, the% kill was determined. 100% means that all larvae were killed; 0% means that no larvae were killed.

In this test, for example, compound 1 of the preparation example kills 100% of the larvae after 7 days at an active compound concentration of 0.1%.

Claims (10)

1. A compound of the formula (I),wherein R is¹Represents alkyl, haloalkyl, alkoxyalkyl, alkylthioalkyl, alkoxy, alkylthio or optionally substituted cycloalkyl, R²Represents hydrogen, halogen, cyano, nitro, thiocyanato, alkoxycarbonyl, alkenyloxycarbonyl, alkylthio, haloalkylthio, alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, haloalkylsulfonyl or thiocarbamoyl, R³Represents hydrogen, alkyl halideThe radicals alkoxyalkyl, alkylcarbonyl, alkylsulfonyl represent arylcarbonyl, arylsulfonyl or arylalkyl, each of which is optionally substituted, or represent optionally substituted cycloalkyl, R⁴Represents optionally substituted aryl, optionally substituted cycloalkyl or optionally substituted cycloalkenyl, and Y represents optionally substituted alkylene, alkenylene or alkyleneoxy.

2. A compound of formula (I) according to claim 1, wherein R¹Represents C₁-C₄Alkyl, C having 1 to 5 identical or different halogen atoms, such as fluorine, chlorine and bromine atoms₁-C₄-haloalkyl group, C₁-C₄-alkoxy-C₁-C₄Alkyl radical, C₁-C₄-alkylthio-C₁-C₄Alkyl radical, C₁-C₄-alkoxy, C₁-C₄-alkylthio, or represents optionally substituted by a group selected from C₁-C₄C mono-to trisubstituted by the same or different substituents of alkyl and halogen₃-C₆-cycloalkyl radical, R²Represents hydrogen, halogen, cyano, nitro, thiocyanato, C₁-C₄Alkoxycarbonyl, C₂-C₄-alkenyloxy-carbonyl, C₁-C₄Alkylthio, C having 1 to 5 identical or different halogen atoms, such as fluorine and chlorine atoms₁-C₄-haloalkylthio, C₁-C₄-alkylsulfinyl, C having 1 to 5 identical or different halogen atoms, such as fluorine and chlorine atoms₁-C₄-haloalkylsulfinyl, C₁-C₄Alkylsulfonyl, C having 1 to 5 identical or different halogen atoms, e.g. fluorine and chlorine atoms₁-C₄-haloalkylsulfonyl or represents thiocarbamoyl, R³Represents hydrogen, C₁-C₄Alkyl, C having 1 to 5 identical or different halogen atoms, such as fluorine and chlorine atoms₁-C₄-haloalkyl group, C₁-C₄-alkoxy-C₁-C₄Alkyl radical, C₁-C₄-alkyl-carbonyl, C₁-C₄-alkylsulfonyl, for phenylcarbonyl, phenylsulfonylOr benzyl, which are in each case optionally mono-to trisubstituted on the phenyl ring by identical or different substituents, possible substituents being in each case halogen, nitro, cyano, C₁-C₄Alkyl, C having 1 to 5 identical or different halogen atoms, such as fluorine and chlorine atoms₁-C₂-haloalkyl group, C₁-C₄-alkoxy, C₁-C₄Alkylthio, C having 1 to 5 identical or different halogen atoms, such as fluorine and chlorine atoms₁-C₂Haloalkoxy or C having 1 to 5 identical or different halogen atoms, such as fluorine and chlorine atoms₁-C₂-haloalkylthio, or represents optionally substituted by a group selected from C₁-C₄C mono-to trisubstituted by the same or different substituents of alkyl and halogen₃-C₆-cycloalkyl radical, R⁴Represents phenyl which is optionally mono-to trisubstituted by identical or different substituents, possible substituents being halogen, nitro, cyano, C₁-C₁₂Alkyl, C having 1 to 5 identical or different halogen atoms, such as fluorine and chlorine atoms₁-C₁₂-haloalkyl group, C₁-C₁₂Alkoxy, C having 1 to 5 identical or different halogen atoms, such as fluorine and chlorine atoms₁-C₁₂-haloalkoxy, C₁-C₁₂Alkylthio, C having 1 to 5 identical or different halogen atoms, such as fluorine and chlorine atoms₁-C₁₂-haloalkylthio, C₂-C₁₂Alkenyl, C having 1 to 5 identical or different halogen atoms, e.g. fluorine and chlorine atoms₂-C₁₂-haloalkenyl, optionally substituted by a group selected from C₁-C₄C mono-to trisubstituted by the same or different substituents of alkyl and halogen₃-C₈-cycloalkyl, and phenyl, phenoxy, phenylthio, benzyl or benzyloxy, each of which is optionally mono-to trisubstituted by identical or different substituents selected from the group consisting of: halogen, nitro, cyano, C₁-C₄Alkyl, C having 1 to 5 identical or different halogen atoms, such as fluorine and chlorine atoms₁-C₄-haloalkyl group, C₁-C₄Alkoxy, C having 1 to 5 identical or different halogen atoms, such as fluorine and chlorine atoms₁-C₄-haloalkoxy, C₁-C₄Alkylthio, C having 1 to 5 identical or different halogen atoms, such as fluorine and chlorine atoms₁-C₄-haloalkylthio, C₁-C₄-alkylthio-C₁-C₄Alkyl radical, C₁-C₄Alkylsulfonyl, C having 1 to 5 identical or different halogen atoms, e.g. fluorine and chlorine atoms₁-C₄-haloalkylsulfonyl, C₁-C₄-alkylcarbonyl group, C₁-C₄Alkoxycarbonyl, thiocarbamoyl, C₁-C₄-alkoxyimino-C₁-C₄-alkyl and optionally C₁-C₄-an alkyl-substituted oxadiazolyl group, or represents C₃-C₈-cycloalkyl or C₅-C₈Cycloalkenyl, each of which is optionally mono-to trisubstituted by identical or different substituents, possible substituents being: c₁-C₄Alkyl, C having 1 to 5 identical or different halogen atoms, such as fluorine and chlorine atoms₁-C₄-haloalkyl group, C₁-C₄Alkoxy, C having 1 to 5 identical or different halogen atoms, such as fluorine and chlorine atoms₁-C₄-haloalkoxy, C₃-C₈-cycloalkyl, and phenyl, the phenyl being optionally mono-to trisubstituted by identical or different substituents selected from the group consisting of: halogen, cyano, nitro, C₁-C₄Alkyl, C having 1 to 5 identical or different halogen atoms, such as fluorine and chlorine atoms₁-C₄-haloalkyl group, C₁-C₄Alkoxy and C having 1 to 5 identical or different halogen atoms, e.g. fluorine and chlorine atoms₁-C₄-haloalkoxy, and Y represents C₁-C₆Alkylene radical, C₁-C₆Hydroxy alkylene, C₁-C₄-alkoxy-C₁-C₆Alkylene radical, C₁-C₄-alkylcarbonyloxy-C₁-C₆Alkylene, cyano-C₁-C₆Alkylene, C having 1 to 5 identical or different halogen atoms, e.g. fluorine and chlorine atoms₁-C₄-a haloalkylene group; c₁-C₄Alkylene oxide radical, C₂-C₄-alkenylene or C₃-C₆-cycloalkyl-C₁-C₄Alkylene, which is optionally mono-to trisubstituted by identical or different substituents from the group consisting of fluorine, chlorine and methyl.

3. A compound of formula (I) according to claim 1, wherein R¹Represents methyl, ethyl, n-or i-propyl, n-, i-, s-or t-butyl; CH (CH)₂F、CHF₂、CF₃、CH₂Cl、CH₂Br、CHClCH₃(ii) a Methoxy, ethoxy, methoxymethyl, ethoxymethyl; methylthiomethyl or cyclopropyl, R²Represents hydrogen, chlorine, bromine, cyano, nitro, thiocyanato; methoxycarbonyl, ethoxycarbonyl, isopropoxycarbonyl, n-propoxycarbonyl; allyloxycarbonyl; SCF₃、SCCl₂F、SOCF₃、SOCCl₂F、SO₂CF₃、SO₂CCl₂F、SCHF₂、SOCHF₂、SO₂CHF₂Or CSNH₂，R³Represents hydrogen, methyl, ethyl, n-or isopropyl; methoxymethyl, ethoxymethyl, n-propoxymethyl, n-butoxymethyl; methylcarbonyl, methylsulfonyl; phenylcarbonyl or benzyl, both of which are optionally mono-or disubstituted by identical or different substituents from the group consisting of fluorine, chlorine, methyl and trifluoromethyl; or cyclopropyl, R⁴Represents phenyl which is optionally mono-to trisubstituted by identical or different substituents, possible substituents being halogen, nitro, cyano, C₁-C₁₂Alkyl, C having 1 to 5 identical or different halogen atoms, such as fluorine and chlorine atoms₁-C₁₂-haloalkyl group, C₁-C₄Alkoxy, C having 1 to 5 identical or different halogen atoms, such as fluorine and chlorine atoms₁-C₄-haloalkoxy, C₁-C₄Alkylthio, C having 1 to 5 identical or different halogen atoms, such as fluorine and chlorine atoms₁-C₄-haloalkylthio, C₂-C₄Alkenyl, C having 1 to 5 identical or different halogen atoms, e.g. fluorine and chlorine atoms₂-C₄Halogenated alkenyl, and phenoxy, phenylthio or benzyloxyEach of which is optionally mono-to trisubstituted with identical or different substituents selected from the group consisting of: halogen, nitro, cyano, C₁-C₄Alkyl, C having 1 to 5 identical or different halogen atoms, such as fluorine and chlorine atoms₁-C₄-haloalkyl group, C₁-C₄Alkoxy, C having 1 to 5 identical or different halogen atoms, such as fluorine and chlorine atoms₁-C₄-haloalkoxy, C₁-C₄Alkylthio, C having 1 to 5 identical or different halogen atoms, such as fluorine and chlorine atoms₁-C₄-haloalkylthio, C₁-C₄-alkylthio-C₁-C₄Alkyl radical, C₁-C₄Alkylsulfonyl, C having 1 to 5 identical or different halogen atoms, e.g. fluorine and chlorine atoms₁-C₄-haloalkylsulfonyl, C₁-C₄-alkylcarbonyl group, C₁-C₄Alkoxycarbonyl, thiocarbamoyl, C₁-C₄-alkoxyimino-C₁-C₂-alkyl and optionally C₁-C₂-alkyl substituted 1,2, 4-oxadiazol-3-yl, and Y represents one of the following groups: -CH₂-,-CH(CH₃)-,-CH(C₂H₅)-,-CH(n-C₃H₇)-,-CH(i-C₃H₇)-,-CH₂CH₂-,-CH(OH)-,-CH(OCH₃)-,-CH(O-CO-CH₃)-,-CH(CN)-,-CHF-,-CHCl-, -CH = CH-or-CH₂O-, where in each case the radical is attached to the thiocarbonyl radical on the left.

4. A compound of formula (I) according to claim 1, wherein R¹Represents methyl, ethyl, n-or i-propyl, n-, i-, s-or t-butyl; CH (CH)₂F、CHF₂、CF₃、CH₂Cl、CH₂Br, methoxy or ethoxy, R²Represents hydrogen, chlorine, bromine, cyano, nitro, thiocyanato, methoxycarbonyl or ethoxycarbonyl, R³Represents hydrogen, methyl, ethyl, methoxymethyl, ethylOxymethyl, methylcarbonyl, phenylcarbonyl or methylsulfonyl, R⁴Represents phenyl, which is optionally mono-to trisubstituted by identical or different substituents, possible substituents being fluorine, chlorine, bromine, nitro, cyano, methyl, ethyl, n-or i-propyl, n-, i-, s-or t-butyl; methoxy, ethoxy, n-or isopropoxy, n-, iso-, sec-or tert-butoxy; methylthio radical, CF₃、OCF₃、OCHF₂、SCF₃、SCCl₂F、CH₂Br、CH₂Cl, and a phenoxy group, the phenoxy group being optionally mono-to trisubstituted by the same or different substituents selected from the group consisting of: 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, thiocarbamoyl, methoxyiminomethyl, 1- (methoxyimino) ethyl, 1- (ethoxyimino) ethyl, 1,2, 4-oxadiazol-3-yl or 5-methyl-1, 2, 4-oxadiazol-3-yl, Y represents-CH₂-or-CH (CH)₃)-。

5. A process for the preparation of a compound of formula (I) according to claim 1, characterized in that A) a compound of formula (II)Wherein R is¹、R²And R³Each as defined in claim 1

a) With a compound of the formula (III),

R⁴-Y-CS-G (Ⅲ)

wherein

R⁴And Y are each as defined in claim 1, and

g represents a leaving group, and the compound is represented by,

or

b) With dithioesters of the formula (IV)

Alk-S-CS-Y-R⁴ (Ⅳ)

Wherein

R⁴And Y are each as defined in claim 1, and

alk represents alkyl or CH₂COOM, wherein

M represents an alkali metal, and M represents an alkali metal,

if appropriate in the presence of a base and, if appropriate, in the presence of a diluent;

or

B) A compound of formula (V)

Wherein

R¹、R²、R³、R⁴And Y are each as defined in claim 1,

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

6. Pesticides, characterized in that they contain at least one compound of formula (i) according to claim 1.

7. The use of compounds of the formula (i) according to claim 1 for controlling pests.

8. A method for controlling harmful organisms, characterized in that a compound of formula (I) is allowed to act on the harmful organisms and/or their habitat.

9. A process for the preparation of a pesticide, characterized in that a compound of formula (i) is mixed with an extender and/or a surfactant.

10. The use of a compound of formula (i) according to claim 1 for the preparation of pesticides.