KR20000029574A - Substituted n-isothiazolyl-(thio)amides - Google Patents

Abstract

PURPOSE: Provided is a method for producing novel N-isothiazolyl-(thio)amides and use thereof for removing animal pests. CONSTITUTION: New N-isothiazolyl-(thio)amides have the formula (I), in which Q stands for the grouping (a), in which Het stands for an optionally substituted heterocycle, and R, X, Y and A have the meanings given in the description. Also provided are several processes for preparing the same and their use for controlling animal pests

Description

Substituted N-isothiazolyl- (thio) amides} Substituted N-isothiazolyl- (thio) amides

It is already known that certain N-isothiazolylamide derivatives have pesticidal properties (see eg EP-A 0 623 282 and WO-A 95/31448).

However, the efficacy and / or duration of action of these prior art compounds is not entirely satisfactory for all areas of use, especially for certain organisms or at low application concentrations.

The present invention relates to novel N-isothiazolyl- (thio) amides, methods for their preparation and their use for removing pests.

Accordingly, the present invention provides novel substituted N-isothiazolyl- (thio) amides of the formula:

Where

Q is a group Wherein Het represents an optionally substituted heterocycle,

R represents hydrogen, alkyl, halogenoalkyl, alkoxyalkyl, alkylcarbonyl, alkyl-sulfonyl, each represents optionally substituted arylcarbonyl, arylsulfonyl or arylalkyl, or optionally substituted cycloalkyl ,

X represents oxygen or sulfur,

Y represents optionally substituted alkylene, alkenylene, alkyleneoxy or alkenylenethio,

A represents optionally substituted aryl, optionally substituted cycloalkyl, optionally substituted cycloalkenyl or optionally substituted heterocycle.

In addition, we found the following:

a) when the aminoisothiazole of formula II is reacted with an acyl halide of formula III in the presence of a base and in the presence of a diluent to obtain a substituted N-isothiazolyl-amide of formula Ia;

b) when reacting the N-isothiazolyl-amide of formula (Ia) obtained in step (a) with a sulfiding agent in the presence of a diluent if appropriate, the following substituted N-isothiazolyl-thioamides of formula (Ib) are obtained;

c) When the aminoisothiazole of formula (II) is reacted with dithioester of formula (IV) in the presence of a diluent if appropriate, also a substituted N-isothiazolyl-thioamide of formula (Ib) is obtained:

Hal-CO-Y-A

Where

Q, R, Y and A are as defined above, respectively.

Hal stands for halogen,

Alk represents alkyl or group MO-CO-CH _2- , where M represents an alkali metal (such as sodium or potassium).

In addition, the fact that the novel substituted N-isothiazolyl- (thio) amides of formula (I) are well suited to combat pests, especially insects, arthropods and nematodes, which occur in the fields of agriculture, forestry, stored food and material protection and hygiene. Figured out.

Illustrative ranges of preferred substituents and / or radicals set forth in the formulas mentioned above and below are as follows.

Q is preferably a group Indicates

Wherein Het represents a 5- or 6-membered heterocycle having one or two heteroatoms, such as N, S and O atoms, optionally substituted one- to trisubstituted by the same or different substituents, and possible substituents are halogen, C ₁ -C ₄ - alkyl, C ₁ -C ₄ - alkoxy, fluorine, chlorine and bromine atoms, such as or a different halogen atom is 1 to 5 C ₁ -C ₄ - halogenoalkyl, C ₁ -C ₄ - alkoxy - C ₁ -C ₄ - alkyl, nitro, C ₁ -C ₄ - alkylsulfonyl, fluorine and chlorine, such as the same or different halogen atom is 1 to 5 C ₁ -C ₄ - halogenoalkyl alkylsulfonyl, and also Thiocarbamoyl.

R is preferably hydrogen, C ₁ -C ₄ - alkyl, fluorine, and the same or different halogen atoms such as chlorine atoms 1 to 5 C ₁ -C ₄ - halogenoalkyl, C ₁ -C ₄ - alkoxy -C ₁ -C ₄ -alkyl, C ₁ -C ₄ -alkylcarbonyl, C ₁ -C ₄ -alkylsulfonyl, or possible substituents in each case are halogen, nitro, cyano, C ₁ -C ₄ -alkyl , C ₁ -C ₂ -halogenoalkyl, C ₁ -C ₄ -alkoxy, C ₁ -C ₄ -alkylthio, fluorine and chlorine atoms having 1 to 5 same or different halogen atoms, such as fluorine and chlorine atoms Phenylcarbonyl, phenylsulfonyl or benzyl, optionally _one- to trisubstituted, in the phenyl ring by the same or different substituents, each of which is C ₁ -C ₂ -halogenoalkoxy having 1 to 5 halogen atoms, the same or different. Or C ₃ -C ₆ -optionally substituted with one to three substituents by the same or different substituents selected from C ₁ -C ₄ -alkyl and halogen. Cycloalkyl.

X preferably represents oxygen or sulfur.

Y is preferably C ₁ -C ₆ -alkylene, C ₁ -C ₆ -hydroxyalkylene, C ₁ -C ₄ -alkoxy-C ₁ -C ₆ -alkylene, C ₁ -C ₄ -alkylcar C ₁ -C ₄ -halogenoalkylene having 1 to 5 same or different halogen atoms, such as carbonyloxy-C ₁ -C ₆ -alkylene, cyano-C ₁ -C ₆ -alkylene, fluorine and chlorine atoms ; Equal selected from fluorine, chlorine and methyl, or one optionally by different substituents to tri substituted, C ₂ -C ₄ - alkylene, C ₁ -C ₄ - alkylene, C ₁ -C ₄ - alkylene-thio Or C ₃ -C ₆ -cycloalkyl-C ₁ -C ₄ -alkylene.

A is preferably

(1) possible substituents are halogen, nitro, cyano, C ₁ -C ₁₂ - same or different halogen atoms, such as alkyl, fluorine and chlorine atoms 1 to 5 C ₁ -C ₁₂ - halogenoalkyl, C ₁ - C ₁₂ - such as alkoxy, fluorine and chlorine atoms, or different 1 to 5 halogen atoms C ₁ -C ₁₂ - halogeno alkoxy, C ₁ -C ₁₂ - alkylthio, such as fluorine and chlorine atoms, or different to halo-halogen atom is 1 to 5 C ₁ -C ₁₂ - halogeno alkylthio, C ₂ -C ₁₂ - alkenyl, fluorine, and the same or different halogen atoms such as chlorine atoms 1 to 5 C ₂ -C ₁₂ C ₃ -C ₈ -cycloalkyl, a group optionally mono- to trisubstituted by the same or different substituents selected from noalkenyl, C ₁ -C ₄ -alkyl and halogen , Phenyl optionally mono- to trisubstituted by the same or different substituents;

Each halogen, nitro, cyano, thio carbamoyl, C ₁ -C ₄ - alkyl, fluorine, and the same or different halogen atoms such as chlorine atoms 1 to 5 C ₁ -C ₄ - halogenoalkyl, C ₁ - C ₄ - alkoxy, C ₁ -C ₄ - alkoxy -C ₁ -C ₄ - alkyl, fluorine and chlorine atoms and the same or different 1 to 5 halogen atoms, such as C ₁ -C ₄ - halogenoalkyl alkoxy, C ₁ - C ₁ -C ₄ -halogenoalkylthio, C ₁ -C ₄ -alkylthio-C ₁ -C ₄ -alkyl, having 1 to 5 same or different halogen atoms, such as C ₄ -alkylthio, fluorine and chlorine atoms, C ₁ -C ₄ -alkylsulfinyl-C ₁ -C ₄ -alkyl, C ₁ -C ₄ -alkylsulfonyl-C ₁ -C ₄ -alkyl, C ₁ -C ₄ -alkylsulfinyl, C ₁ -C C ₁ -C ₄ -halogenoalkylsulfonyl having 1 to 5 same or different halogen atoms such as ₄ -alkylsulfonyl, fluorine and chlorine atoms, formyl, C ₁ -C ₄ -alkylcarbonyl, C _1- C ₄ -alkoxy-carbonyl, C ₁ -C ₄ -alkoxyimino-C ₁ -C ₄ -alkyl, optionally C ₁ -C ₄ -alkyl-substituted oxadiazolyl and groups or Phenyl, phenoxy, phenylthio, benzyl, benzyloxy, pyridyloxy, pyrimidyloxy, pyrazinyloxy or pyridazinyloxy optionally substituted one- to trisubstituted by the same or different substituents selected from one of Or;

(2) The possible substituents are C ₁ -C ₄ - alkyl, fluorine and chlorine, such as or different halogen atom is 1 to 5 C ₁ -C ₄ - halogenoalkyl, C ₁ -C ₄ - alkoxy, fluorine, and the same or different halogen atoms such as chlorine atoms 1 to 5 C ₁ -C ₄ - halogenoalkyl alkoxy, C ₃ -C ₈ - cycloalkyl or equal to one, optionally by different substituents to be ohchihwan C ₅ -C ₈ cycloalkenyl or C ₃ -C ₈ - cycloalkyl, and halogen, cyano, nitro, C ₁ -C ₄ - alkyl, fluorine and chlorine atoms and the same or different halogen atoms, such as 1 to 5 C ₁ -C ₄ - halogenoalkyl, C ₁ -C ₄ - alkoxy, fluorine and the like, such as a chlorine atom or different halogen atom is 1 to 5 C ₁ -C ₄ - alkoxy or equal selected from halogeno different substituents Phenyl optionally substituted by one to trisubstituted;

(3) 1 to 3 heteroatoms such as N, S and O atoms, and may optionally also contain one or more CO and / or CS groups as ring members, possible substituents being halogen, nitro, cyano, C ₁ -C ₄ - alkyl, C ₁ -C ₄ - alkoxy, C ₁ -C ₄ - alkylthio, fluorine, and the same or different halogen atoms such as chlorine atoms 1 to 5 C ₁ -C ₄ - halogenoalkyl, fluorine and the same or different halogen atoms such as chlorine atoms 1 to 5 C ₁ -C ₄ - halogeno-alkoxy, fluorine, and the same or different halogen atoms such as chlorine atoms 1 to 5 C ₁ -C ₄ - halogenoalkyl Thioine to a 5- or 6-membered heterocycle optionally substituted _one- to trisubstituted by the same or different substituents, or possible substituents are halogen, nitro, cyano, C ₁ -C ₄ -alkyl, C ₁ -C ₄ -alkoxy, C ₁ -C ₄ - alkylthio, such as fluorine and chlorine atoms, or And 1 to 5 halogen atoms other personal C ₁ -C ₄ - halogenoalkyl, fluorine, and the same or different halogen atoms such as chlorine atoms 1 to 5 C ₁ -C ₄ - alkoxy halogeno, such as fluorine and chlorine atoms NH, which may be optionally mono- to trisubstituted by the same or different substituents each having the same or different halogen atoms of 1 to 5 C ₁ -C ₄ -halogenoalkylthio, which may optionally be present in the heterocycle instead of the hydrogen atom With C ₁ -C ₄ -halogenoalkyl, C ₁ -C ₄ -alkoxy or fluorine or chlorine atoms, wherein the group is 1 to 5 halogen atoms, the same or different, such as C ₁ -C ₆ -alkyl, halogen, fluorine or chlorine atoms By C ₁ -C ₆ -alkyl, C ₁ -C ₆ -alkylcarbonyl or phenylsulfonyl, which in turn is optionally substituted by C ₁ -C ₄ -halogenoalkoxy having 1 to 5 same or different halogen atoms Phenyl, which may be substituted Indicate noksi, phenylthio or benzyl or;

(4) It may also contain one or more heteroatoms such as O, S or N atoms, or one or more CO groups as ring members and possible substituents are halogen, nitro, cyano, C ₁ -C ₄ -alkyl C ₁ -C ₄ -halogenoalkyl, C ₁ -C ₄ -alkoxy-C ₁ -C ₄ -alkyl, C ₁ -C ₄ -alkoxy, having 1 to 5 same or different halogen atoms, such as fluorine and chlorine atoms C ₁ -C ₄ -halogenoalkoxy, C ₁ -C ₄ -alkylthio, C ₁ -C ₄ -alkylthio, fluorine and chlorine atoms having 1 to 5 same or different halogen atoms, such as fluorine and chlorine atoms. 5 individual C ₁ -C ₄ - halogenoalkyl alkylthio, C ₁ -C ₄ - alkylsulfinyl, C ₁ -C ₄ - alkylsulfonyl, hydroxyl, mercapto, C ₁ -C ₄ - alkylcarbonyl, fluorinated And C ₁ -C ₄ -halogenoalkyl-carbonyl, C ₁ -C ₄ -alkoxy-car, having 1 to 5 same or different halogen atoms such as chlorine atoms Represent condensed di- or tricyclic radicals optionally substituted one- to five-substituted by the same or different substituents which are levonyl, in particular possible substituents on the phenyl moiety are halogen, nitro, cyano, C ₁ -C ₄ -alkyl, Same as C ₁ -C ₄ -alkoxy, C ₁ -C ₄ -alkylthio, fluorine and chlorine atoms, or the same as C ₁ -C ₄ -halogenoalkyl having 1 to 5 halogen atoms, such as fluorine and chlorine atoms C ₁ -C ₄ -halogenoalkoxy having 1 to 5 different or different halogen atoms, and the same or different C ₁ -C ₄ -halogenoalkylthio having 1 to 5 halogen atoms, such as fluorine and chlorine atoms. Phenyl, phenoxy, phenylthio or benzyl, each optionally mono- to trisubstituted by other substituents;

here,

R ¹ represents C ₁ -C ₄ -halogenoalkyl having 1 to 5 same or different halogen atoms, such as hydrogen, C ₁ -C ₈ -alkyl, fluorine and chlorine atoms, or halogen and C ₁ -C _4- C ₃ -C ₇ -cycloalkyl which is optionally mono- or polysubstituted by the same or different substituents selected from alkyl, or possible substituents are halogen, C ₁ -C ₄ -alkyl or C ₁ -C ₄ -alkoxy Phenyl optionally mono- to trisubstituted by the same or different substituents,

R ² and R ³ are the same or different and each represents hydrogen or C ₁ -C ₄ -alkyl;

Among alkyl - R ⁴ is C ₁ -C ₈ - alkyl, such as fluorine and chlorine atoms, or different halogen atoms 1 to 5 C ₁ -C ₄ - halogenoalkyl, or represents a halogen, and C ₁ -C ₄ Equal to or optionally substituted with the same or different substituents selected from C ₃ -C ₇ -cycloalkyl, or the possible substituents are halogen, C ₁ -C ₄ -alkyl or C ₁ -C ₄ -alkoxy Phenyl optionally mono- to trisubstituted by different substituents;

W represents oxygen or one of the groups = N-OR ⁵ and = N-NR ⁶ R ⁷ ,

here,

R ⁵ represents C ₁ -C ₆ -alkyl or C having 1 to 5 same or different halogen atoms such as halogen, nitro, cyano, thiocarbamoyl, C ₁ -C ₄ -alkyl, fluorine and chlorine atoms C having 1 to 5 halogen atoms, such as ₁ -C ₄ -halogenoalkyl, C ₁ -C ₄ -alkoxy, C ₁ -C ₄ -alkoxy-C ₁ -C ₄ -alkyl, fluorine and chlorine atoms ₁ -C ₄ - halogenoalkyl alkoxy, C ₁ -C ₄ - alkylthio, fluorine, and the same or different halogen atoms such as chlorine atoms 1 to 5 C ₁ -C ₄ - halogenoalkyl alkylthio, C ₁ -C ₄ -Alkylthio-C ₁ -C ₄ -alkyl, C ₁ -C ₄ -alkylsulfinyl-C ₁ -C ₄ -alkyl, C ₁ -C ₄ -alkylsulfonyl-C ₁ -C ₄ -alkyl, C ₁ -C ₄ - alkylsulfinyl, C ₁ -C ₄ - alkylsulfonyl, fluorine, and the same or different halogen atoms such as chlorine atoms 1 to 5 C ₁ -C ₄ - halogenoalkyl - sulfonyl, formyl, C ₁ -C ₄ - alkyl-carbonyl, C ₁ -C ₄ - alkoxy-carbonyl and C ₁ -C ₄ - Al Shi unexposed -C ₁ -C ₄ - alkyl or selected from the same one with each other, optionally by another substituent-to three denotes a substituted benzyl that is;

R ⁶ and R ⁷ are the same or different and each represents hydrogen, C ₁ -C ₆ -alkyl or possible substituents are the same or different from each other, such as halogen, nitro, cyano, C ₁ -C ₄ -alkyl, fluorine and chlorine atoms the other halogen atom is 1 to 5 C ₁ -C ₄ - halogenoalkyl, C ₁ -C ₄ - alkoxy, or fluorine, and the same or different halogen atoms such as chlorine atoms 1 to 5 C ₁ -C ₄ - halogenoalkyl alkoxy Phenyl optionally mono- to trisubstituted by the same or different substituents.

Q particularly preferably represents one of the following groups,

here,

Z ¹ , Z ² and Z ³ are the same or different and each is hydrogen, chlorine, bromine, nitro, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl; CH ₂ F, CHF ₂ , CF ₃ , CH ₂ Cl, CH ₂ Br, CHClCH ₃ ; Methoxy, ethoxy, methoxymethyl or ethoxymethyl.

R is particularly preferably hydrogen, methyl, ethyl, n- or i-propyl; Methoxymethyl, ethoxymethyl, n-propoxymethyl, n-butoxymethyl; Methyl-carbonyl, methylsulfonyl; Each represents phenylcarbonyl or benzyl or cyclopropyl, optionally mono- or di-substituted by the same or different substituents selected from fluorine, chlorine, methyl or trifluoromethyl.

X particularly preferably represents oxygen or sulfur.

Y particularly preferably represents one of the following groups:

-CH _2- , -CH (CH ₃ )-, CH (C ₂ H ₅ )-, CH (nC ₃ H ₇ )-, -CH (iC ₃ H ₇ )-, -CH ₂ -CH ₂ -,- CH (OH)-, -CH (OCH ₃ )-, -CH (O-CO-CH ₃ )-, -CH (CN)-, -CHF-, -CHCl-, -CH-[-◁]-, -CH = CH- or -CH ₂ O-.

A is particularly preferably

(1) possible substituents are halogen, nitro, cyano, C ₁ -C ₁₂ - same or different halogen atoms, such as alkyl, fluorine and chlorine atoms 1 to 5 C ₁ -C ₁₂ - halogenoalkyl, C ₁ - C ₄ -, such as alkoxy, fluorine and chlorine atoms, or different halogen atoms 1 to 5 C ₁ -C ₄ - halogenoalkyl alkoxy, C ₁ -C ₄ - alkylthio, fluorine and chlorine atoms, such as, or different a halogen atom is 1 to 5 C ₁ -C ₄ - halogenoalkyl alkylthio, C ₂ -C ₄ - alkenyl, fluorine, and the same or different halogen atoms such as chlorine atoms 1 to 5 C ₂ -C ₄ - halogeno Noalkenil, group , Phenyl optionally mono- to trisubstituted by the same or different substituents;

Each halogen, nitro, cyano, thio carbamoyl, C ₁ -C ₄ - alkyl, fluorine, and the same or different halogen atoms such as chlorine atoms 1 to 5 C ₁ -C ₄ - halogenoalkyl, C ₁ - C ₄ - alkoxy, C ₁ -C ₄ - alkoxy -C ₁ -C ₄ - alkyl, fluorine and chlorine atoms and the same or different 1 to 5 halogen atoms, such as C ₁ -C ₄ - halogenoalkyl alkoxy, C ₁ - C ₁ -C ₄ -halogenoalkylthio, C ₁ -C ₄ -alkylthio-C ₁ -C ₄ -alkyl, having 1 to 5 same or different halogen atoms, such as C ₄ -alkylthio, fluorine and chlorine atoms, C ₁ -C ₄ -alkylsulfinyl-C ₁ -C ₄ -alkyl, C ₁ -C ₄ -alkylsulfonyl-C ₁ -C ₄ -alkyl, C ₁ -C ₄ -alkylsulfinyl, C ₁ -C C ₁ -C ₄ -halogenoalkylsulfonyl having 1 to 5 same or different halogen atoms such as ₄ -alkylsulfonyl, fluorine and chlorine atoms, formyl, C ₁ -C ₄ -alkylcarbonyl, C _1- C ₄ -alkoxy-carbonyl, C ₁ -C ₄ -alkoxyimino-C ₁ -C ₂ -alkyl, optionally C ₁ -C ₂ -alkyl-substituted oxadiazol-3-yl and groups or Phenyloxy, phenylthio, benzyloxy or pyridyloxy, optionally mono- to trisubstituted by the same or different substituents selected from one of:

(2) cyclopentyl, cyclohexyl, cyclophene, each optionally substituted one- to five-substituted by the same or different substituents, wherein the possible substituents are fluorine, chlorine, bromine, methyl, ethyl, isopropyl, methoxy propylene trifluoromethyl; Tenyl or cyclohexenyl;

(3) suitable substituents for each case include fluorine, chlorine, nitro, cyano; Methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl; Methoxy, ethoxy, n- or i-propoxy; Methylthio; -CF ₃ , -CHF ₂ , -CH ₂ CF ₃ , -CH ₂ -CF ₂ -CHF ₂ , -CH (CF ₃ ) -CH ₃ ; _{-OCF 3, -OCHF 2, OCH 2} CF 3, -O-CH 2 -CF 2 -CF 3, -OCH 2 -CF 2 -CHF 2, -O-CH (CF 3) -CH 3; One of the following heterocycles optionally mono- or disubstituted by the same or different substituents -SCF ₃ ;

Each possible by the same or different substituents, wherein the possible substituents are fluorine, chlorine, nitro, cyano, methyl, ethyl, methoxy, ethoxy, methylthio, trifluoromethyl, trifluoromethoxy or trifluoromethylthio Phenyl, phenoxy or phenylthio, mono- or disubstituted,

here,

R ⁸ is C ₁ -C ₄ -alkyl, in particular methyl or ethyl; C ₁ -C ₄ -alkylcarbonyl, in particular methylcarbonyl or ethylcarbonyl; Also C ₁ -C ₄ -alkyl, in particular methyl or ethyl; Halogen, in particular fluorine or chlorine; C ₁ -C ₄ -halogenoalkyl, in particular trifluoromethyl; C ₁ -C ₄ -alkoxy, in particular methoxy; And C ₁ -C ₄ -halogenoalkoxy, especially phenylsulfonyl, optionally mono- or disubstituted by the same or different substituents selected from trifluoromethoxy;

(4) bound if necessary and possible substituents in each case are fluorine, chlorine, bromine, nitro, cyano; Methyl, ethyl; Methoxy, methylthio, trifluoromethyl, trifluoromethoxy or trifluoromethylthioin represents the following di- or tricyclic radicals optionally mono- to tetrasubstituted by the same or different substituents:

here,

R ¹ represents hydrogen, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl or is optionally substituted by the same or different substituents selected from fluorine, chlorine, bromine and methyl -To optionally substituted by the same or different substituents representing C ₃ -C ₇ -cycloalkyl or possible substituents are fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, methoxy or ethoxy Phenyl mono- to trisubstituted;

R ² and R ³ are the same or different and each represents hydrogen, methyl, ethyl, n- or i-propyl, n-, i- or s- or t-butyl;

R ⁴ represents methyl, ethyl, n- or i-propyl, n-, i- or s- or t-butyl, or is optionally substituted with the same or different substituents selected from fluorine, chlorine, bromine and methyl; C ₃ -C ₇ -cycloalkyl which is missubstituted (preferably mono- to trisubstituted) or possible substituents are fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, methoxy or ethoxy Phenyl optionally mono- to trisubstituted by the same or different substituents;

W represents oxygen or one of the groups = N-OR ⁵ and = N-NR ⁶ R ⁷ ,

here,

R ⁵ represents C ₁ -C ₄ -alkyl, or possible substituents are fluorine, chlorine, bromine, cyano, nitro, trifluoromethyl, trifluoromethoxy, methylthio, methylsulfinyl, methylsulfonyl, methyl Benzyl optionally substituted one- to trisubstituted by the same or different substituents which are ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy or ethoxy;

R ⁶ and R ⁷ are the same or different and each represents hydrogen, C ₁ -C ₄ -alkyl, or possible substituents are fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, trifluoromethyl, methoxy or Phenyl optionally mono- to trisubstituted by the same or different substituents which are trifluoromethoxy.

Q very particularly preferably represents one of the following groups:

here,

Z ¹ and Z ² are the same or different and represent hydrogen, chlorine, bromine, nitro, methyl, ethyl, methoxy or ethoxy, respectively.

R very particularly preferably represents hydrogen, methyl, ethyl, methoxymethyl, ethoxymethyl, methylcarbonyl, phenylcarbonyl or methylsulfonyl.

X very particularly preferably represents oxygen or sulfur.

Y very particularly preferably represents —CH ₂ —.

A is very particularly preferably a possible substituent is 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, CF ₃ , OCF ₃ , OCHF ₂ , SCF ₃ , SCCl ₂ F; CH ₂ Br, CH ₂ Cl; group Phenyl optionally mono- to trisubstituted by the same or different substituents; Also fluorine, chlorine, bromine, nitro, cyano, thiocarbamoyl, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, n-, s- or t-butoxy; Methylthio, methylthiomethyl, CF ₃ , OCF ₃ , OCHF ₂ , SCF ₃ , SCCl ₂ F; CH ₂ Br, CH ₂ Cl, methoxycarbonyl, methylsulfinyl, methylsulfonyl, trifluoromethylsulfonyl or a group Phenoxy optionally substituted with one- to three-substituted by the same or different substituents selected from among;

here,

R ¹ represents hydrogen, methyl or ethyl;

R ² and R ³ are the same or different and each represents hydrogen or methyl;

R ⁴ represents methyl or ethyl;

W represents oxygen or a group = N-OR ⁵ ,

here,

R ⁵ represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl or possible substituents are fluorine, chlorine, bromine, nitro, cyano, methyl, ethyl, methoxy or Benzyl optionally mono- to trisubstituted in the ring by the same or different substituents which are ethoxy.

Preferred compounds according to the invention are substances of the formulas IA to ID:

Where

R, Z ¹ and Z ² each have the general, preferred, particularly preferred and very particularly preferred meanings mentioned above,

X ¹ , X ² , X ³ , X ⁴ and X ⁵ represent substituents mentioned above as general, preferred, particularly preferred and very particularly preferred for phenyl and / or phenoxy radicals under A,

X ¹ , X ² , X ³ and X ⁴ may in each case also represent hydrogen.

Further preferred compound groups are compounds of the formulas (IA) to (ID) in which the phenoxy radicals are present in the para position with respect to the NR-CO-CH ₂ -or NR-CS-Ch ₂ -groups, among which the substituents X ¹ , Particular preference is given to compounds in which X ² , X ³ and X ⁴ represent hydrogen.

The general or preferred radical definitions or examples mentioned above apply to both the final product and the corresponding starting materials and intermediates. These radical definitions may be combined with one another, if desired, ie including combinations between the respective preferred ranges.

Preference is given to compounds of the formula (I) which, according to the invention, comprise as preferred combinations of the meanings mentioned above.

Particular preference is given to compounds of the formula I in which the combinations of the meanings mentioned above according to the invention are included as particularly preferred.

Very particular preference is given to compounds of the formula (I) which comprise according to the invention combinations of the meanings mentioned above as very particularly preferred.

In the radical definitions given above and below, hydrocarbon radicals such as alkyl or alkenyl- and in combination with heteroatoms such as alkoxy or alkylthio are in each case as straight or branched as possible.

Examples of newly substituted N-isothiazolyl- (thio) amides are shown in Tables 1-9:

The compounds in Table 1 correspond to Formula I, where the substituent definitions are as follows:

Q =

R = H

X = O

Y = CH ₂

A = presented below:

Table 2 includes compounds of Formula I in which the substituent definitions are as follows: Y = CH (CH ₃ ) Q, R, X and A = as shown in Table 1.

Table 3 includes compounds of Formula I, wherein the substituent definitions are as follows: Q = R, X, Y and A = as shown in Table 1.

Table 4 includes compounds of Formula I in which the substituent definitions are as follows: X = SQ, R, Y and A = as shown in Table 3.

Table 5 includes compounds of Formula I, wherein the substituent definitions are as follows: Q = R, X, Y and A = as shown in Table 1.

Table 6 includes compounds of Formula I, wherein the substituent definitions are as follows: Q = R, X, Y and A = as shown in Table 1.

Table 7 includes compounds of Formula I, wherein the substituent definitions are as follows: Q = R, X, Y and A = as shown in Table 1.

Table 8 includes compounds of Formula I in which the substituent definitions are as follows: R = HX = OY = CH ₂ A = Q = as shown below:

Table 9 includes compounds of Formula I, wherein the substituent definitions are as follows: A = Q, R, X and Y = as shown in Table 8.

For example, thieno [2,3c] isothiazol-3-yl-amine and [4- (4-cyanophenoxy)]-phenyl as starting materials in the preparation of compounds of formula (Ia) according to process (a). When using -acetyl chloride, the reaction route can be represented by the following scheme:

For example, thieno [2,3c] isothiazol-3-yl- [4- (4-nitrophenoxy)] phenyl-acetyl-amine as starting material in the preparation of the compound of formula Ib according to step (b). When using Lawesson reagent (2,4-bis- (4-methoxyphenyl) -1,3-dithia-2,4-diphosphetane 2,4-disulfide) as a sulfiding agent, The reaction pathway can be represented by the following scheme:

For example, thieno [2,3c] isothiazol-3-yl-amine and methyl [4- (4-chlorophenoxy)]-phenyl as starting materials in the preparation of compounds of formula (Ib) according to process (c). When using dithioacetate, the reaction pathway can be represented by the following scheme:

The aminoisothiazoles of formula (II) to be used as starting materials in processes (a) and (c) according to the invention are known (see example GB 1568388; J. Chem. Res. Synop. 1989, 29; DE-A 2713573 Can. J. Chem. 1973 (51), 1742 or JP 05070469) and / or known methods (see, eg, references cited above).

They may also first react an aminonitrile derivative of formula (V) with hydrogen sulfide in the presence of a base, such as pyridine or triethylamine, for example, and then obtain a thioamide derivative of formula (VI) for example H ₂ O ₂ bromine or It can be obtained by oxidizing as an oxidizing agent such as sodium hypochlorite:

Where

Het is as defined above.

Aminonitrile derivatives of Formula V are known (see, eg, EP-A 0 453 611; Acta Chim. Scand., B. 1975, B 29 (2), 224; DE-A 2713573; Chem. Pharm. Bull. 1971, 19, 119; Tetrahedron Letters, 1989, 30, 2631; J. Chem. Soc., Perkins Trans I, 1987, 1521; Helv. Chim. Acta 1975, 58, 2192; J. Med. Chem. 1987, 30 , 91; J. Het. Chem. 1985, 22, 1093 or EP-A 0 636 626), and / or they may be prepared by known methods (see, eg, references cited above).

Acyl halides of the general formula (III) to be further used as starting materials in process (a) according to the invention are generally known compounds of organic chemistry. In formula (III), Hal preferably represents chlorine or bromine.

Dithioesters of the general formula (IV) to be further used as starting materials in process (c) according to the invention are known (see, eg, Tetrahedron 2663 (1984) or J. Chem Research (M) 2701 (1988)), and / Or they can be prepared by similar known processes. In formula (IV), Alk preferably represents methyl.

Preferred diluents for carrying out process (a) according to the invention are optionally halogenated aliphatic or aromatic hydrocarbons, ethers or nitriles such as cyclohexane, toluene, chlorobenzene. Chloroform, dichloromethane, dichloroethane, dioxane, tetrahydrofuran, diethyl ether or acetonitrile.

Suitable bases for process (a) are all conventional proton acceptors. Preference is given to using alkali metal or alkaline earth metal hydroxides, alkali metal or alkaline earth metal carbonates or bicarbonates or nitrogen bases. Sodium hydroxide, calcium hydroxide, potassium carbonate, sodium bicarbonate, triethylamine, dibenzylamine, diisopropylamine, pyridine, quinoline, diazabicyclooctane (DABCO), diazabicyclononene (DBN) and diazabicycloundecene ( DBU) may be mentioned.

In process (a) the reaction temperature can be varied within a relatively wide range. In general, the reaction is carried out at a temperature of -40 ° C to + 200 ° C, preferably 0 ° C to 100 ° C.

When carrying out process (a), the acyl halide of formula III is generally used at 1 to 2 moles, preferably 1 to 1.5 moles per mole of aminoisothiazole of formula II.

In some cases it is useful to use the aminoisothiazoles of formula II in the form of their hydrohalides, such as hydrochloride.

Preferred sulfiding agents for carrying out process (b) according to the invention are phosphorus pentasulfide or Lawesson's reagent [2,4-bis (4-methoxy-phenyl) -1,3,2,4-dithiadiphosphane -2,4-dithione] (Examples Tetraheadon 41, 22,5061 ff (1985)).

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

When carrying out process (b) according to the invention, the reaction temperature can be carried out within a relatively wide range. In general, the reaction is carried out at a temperature of 0 ° C to 200 ° C, preferably 20 ° C to 150 ° C.

When carrying out process (b) according to the invention, generally 1 to 3 moles, preferably 1 to 2 moles, of sulfiding agents are used per mole of formula (Ia). Processing is performed by a conventional method.

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

However, the reaction can be carried out in a pure state without solvent.

When carrying out process (c) according to the invention, the reaction temperature can be varied within a relatively wide range. In general, the reaction is carried out at a temperature of 0 ° C to 150 ° C, preferably 20 ° C to 120 ° C.

When carrying out process (c) according to the invention, the dithioester of formula IV is generally used at 1 to 3 moles, preferably 1 to 1.5 moles per mole of aminoisothiazole of formula II. Processing and separation are carried out by conventional methods.

Active compounds with good harvest resistance and low toxicity to warm-blooded animals are suitable for eliminating pests, especially insects, arthropods and nematodes, encountered in the fields of agriculture, forestry, preserving food and materials, and sanitation. These can preferably be used as crop protection agents. They are usually active against sensitive and resistant species and against all or many stages of development. The pests mentioned above include:

The order of Isopoda, for example Oniscus asellus, Armadillidium vulgare and Porcellio scaber;

Neck of Diloplopoda, for example Blaniulus guttulatus;

From the neck of Chilopoda, for example Geophilus carpophagus and Scutigera spec .;

The tree of Symmphyla, for example Scutigerella immaculata;

The neck of Thysanura, for example Lepisma saccharina;

The neck of Collembola, for example Onychiurus armatus;

Orthoptera, for example, Blata orientalis, Periplaneta americana, Leucophaea maderae, Blatella germanica, Ah Keta Domestikus, Gryllotalpa spp., Locusta migratoria migratorioides, Melanoplus differentialis and Systoser Schistocerca gregaria;

From the order of the dermaptera, for example Porficula auricularia;

The termite Isoptera, for example Reticulitermes spp .;

Anoplura, for example Pediculus humanus corporis, Haematopinus spp. And Linognathus spp .;

Mallophaga necks, for example Trichodectes spp. And Damaliane spp .;

Throats of Thysanoptera, for example Hercinothrips femoralis and Tripps tabaci;

From the order of Heteroptera, e.g., Eurygaster spp., Dysdercus intermedius, Piesma quadrata, Cimex lectularius, Rodney Rhodnius prolixus and Triatoma spp .;

The cicada (Homoptera), for example Aleurodes brassicae, Bemisia tabaci, Trialeurodes vaporariorum, Apis gossypii, Brevicoryne brassicae, Cryptomyzus ribis, Apis fabae, Apis pomi, Eriosoma lanigerum, hyaloptherus arundi Niceopterus arundinis, Phylloxera vastatrix, Pemphigus spp., Macrosiphum avenae, Myzus spp., Phorodon humuli ), Rhopalosiphum padi, Empoasca spp., Eucelis bilobatus, Nephotettix cincticeps, Lecanium corni , Cissetia oleea (Saissetia) oleae, Laodelphax striatellus, Nilaparvata lugens, Aonidiella aurantii, Aspidiotus hederae, Pseudoco Pseudococcus spp. And Psylla spp .;

Lepidoptera, for example, Pectinophora gossypiella, Bupalus piniarius, Cheimatobia brumata, Lithocolletis blancardella, Hyponomeuta padella, Plutella maculipennis, Malacosoma neustria, Euprotis chrysorrhoea, Lymantria spp. , Buculatrix thurberiella, Phyllocnistis citrella, Agrotis spp., Euxoa spp., Feltia spp., Et al. Earias insulana, Heliothis spp., Spodoptera exigua, Mamestra brassicae, Panolis flammea, Spodorftera Spodopter litura, Spodoptera spp., Trichoplusia ni, Carpocapsa pomonella, Pieris spp., Chilo species spp.), Pyrausta nubilalis, Ephestia kuehniella, Galleria mellonella, Tineola bisselliella, Tinnea pelionella pleeionella, Hofmannophila pseudospretella, Cacoecia podana, Capua reticulana, Choristoneura fumiferana, Celia ambigu Clysia ambiguella, Homona magnanima, and Tortrix viridana;

Neck of Coleoptera, for example, Anobium punctatum, Rhizopertha dominica, Bruchidius obtectus, Acanthoscelides obtectus , Hylotrupes bajulus, Agelastica alni, Leptinotarsa decemlineata, Phaedon cochleariae, Diabrotica spp. .), Psylliodes chrysocephala, Epilachna varivestis, Atomaria spp., Oryzaephilus surinamensis, Antoninomus species (Anthonomus spp.), Sitophilus spp., Otiorrhynchus sulcatus, Cosmopolites sordidus, Cethorrinkus assimilus assimilis, Hypera postica, Dermestes spp., Trogoderma spp., Anthrasno spp., Atagonus spp. ), Lyctus spp., Meligethes aeneus, Pintin spp., Niptus hololeucus, Gibbium psylloides , Tribolium spp., Tenebrio molitor, Agriotes spp., Conoderus spp., Melonta melolontha, Amphi Amphimallon solstitialis and Costelitra zealandica;

The order of the Hymenoptera, for example Diprion spp., Hoplocampa spp., Lasius spp., Monomorium pharaonis and Vespa species ( Vespa spp.);

Diptera, for example Aedes spp., Anopheles spp., Culex spp., Drosophila melanogaster, Musca species ( Musca spp.), Fannia spp., Califora erythrocephala, Lucilia spp., Chrysomyia spp., Cuterebra spp. spp.), Gastrophilus spp., Hippobosca spp., Stomoxys spp., Oestrus spp., Hypoderma spp. .), Tabanus spp., Tannia spp., Bibio hortulanus, Oscinella frit, Phorbia spp., Pegomia Pegomyia hyoscyami, Ceratitis capitata, Dacus loeae and Tipila paludosa.

Siphonaptera, for example Xenopsylla cheopis, Ceratophyllus spp. And Ctenocephalides felis.

Arachnida necks such as Scorpio maurus and Latrodectus mactans.

The order of the ticks Acarina, for example, Acarus siro, Argas spp., Ornithodoros spp., Dermanyssus spp. Eriophyes ribis, Phyllocoptruta oleivora, Bophylus spp., Ripicephalus spp., Amblyomma spp., Hyalomma spp. ), Ixodes spp., Psoroptes spp., Chorioptes spp., Sarcoptes spp., Tarsonemus spp. , Bryobia praetiosa, Panonicus spp., And Tetranychus spp.

Phytoparasitic nematodes include, for example, Pratylencus spp., Radopholus similis, Ditylenchus dipsaci, Tylenkulus semipenetrans Heterodera spp., Globoderra spp., Melodogyne spp., Aphelenchoides spp., Longidorus spp. Pinema spp. And Trichodorus spp.

The compounds of the formula (I) according to the invention have particularly pronounced pesticidal activity.

They can be used particularly successfully to get rid of plant-harmful insects. They have strong activity against, for example, mustard helmet larvae (Phaedon cocleariae), owl moth larvae (Spodoftera fruitgiferda) and strong against green rice leaf locusts (nepotetics syntaccepts). There is activity.

The active compounds are conventional formulations such as liquids, emulsions, wettable powders, suspensions, powders, dusting agents, pastes, soluble powders, granules, suspension-emulsion concentrates, natural and synthetic substances impregnated with the active compounds. And microcapsules in the polymeric material.

These formulations are prepared, for example, by known methods and are preferably prepared by mixing the active compounds with extenders, ie liquid solvents and / or solid carriers, optionally using surfactants, ie emulsifiers and / or dispersants and / or blowing agents. .

When water is used as an extender, for example, an organic solvent can also be used as an auxiliary solvent. In essence, suitable liquid solvents are: aromatic compounds such as xylene, toluene or alkylnaphthalene, chlorinated aromatic or chlorinated aliphatic hydrocarbons such as chlorobenzene, chloroethylene or methylene chloride, cyclohexane or paraffins, for example mineral oil fractions. Polar acids such as aliphatic hydrocarbons such as mineral and vegetable oils, alcohols such as butanol or glycols and ethers and esters thereof, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, dimethylformamide and dimethyl sulfoxide Solvent, and also water.

Suitable solid carriers are, for example, ground natural minerals such as kaolin, clay, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, and ground synthetic minerals such as finely divided silica, alumina and silicates; Suitable granular carriers for granules are for example synthetic granules of ground and classified natural rocks and inorganic and organic powders such as calcite, marble, pumice, calcite and dolomite, and organic materials such as sawdust, coconut husks, corncobs and tobacco stems. Granules of; Suitable emulsifiers and / or blowing agents are, for example, nonionic and anionic emulsifiers such as polyoxyethylene fatty alcohol ethers such as polyoxyethylene fatty acid esters, alkylaryl polyglycol ethers, alkylsulfonates, alkyl sulfates, aryl sulfonates and proteins Hydrolyzate; Suitable dispersants are, for example, lignin-sulfite waste liquors and methylcellulose.

Adhesives such as carboxymethylcellulose, gum arabic, polyvinyl alcohol and polyvinyl acetate such as powders, natural and synthetic polymers in the form of granules or emulsions, besides natural phospholipids such as cephalin and lecithin, and synthetic phospholipids Can be used. Other possible additives are mineral and vegetable oils.

Inorganic pigments such as iron oxide, titanium oxide and prussian blue, and colorants such as alizarin dyes, azo dyes and organic dyes such as metal phthalocyanine dyes and micronutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc Can be used.

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

The active compounds according to the invention are prepared from commercial preparations and from these preparations as a mixture with other active compounds such as insecticides, attractants, fungicides, fungicides, acaricides, nematicides, fungicides, growth-regulating substances or herbicides. May exist in the form. Pesticides include, for example, phosphoric esters, carbamates, carboxylic esters, chlorinated hydrocarbons, phenylureas, substances produced by microorganisms and the like.

Particularly useful 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'-trifluoro-methyl-1,3-thiazole-5-carboxanilide; 2,6-dichloro-N- (4-trifluoromethylbenzyl) -benzamide; (E) -2-methoxyimino-N-methyl-2- (2-phenoxyphenyl) -acetamide; 8-hydroxyquinoline sulfate; Methyl (E) -2- {2- [6- (2-cyanophenoxy) -pyrimidin-4-yloxy] -phenyl} -3-methoxyacrylate; Methyl (E) -methoximino [alpha- (o-tolyloxy) -o-tolyl] acetate; 2-phenylphenol (OPP), Aldimorph, Ampropyl Force, Aniazine, Azaconazole, Benalacyl, Benodanil, Benomil, Binapacryl, Biphenyl, Vitertanol, Blastisidin-S, Bromuconazole, burimate, butiobate, calcium polysulfide, captapol, captan, carbendazim, carboxycin, quinomethionate, chloroneb, chloropicrine, chlorothalonil, clozolinate, cupraneb, Cymoxanyl, cyproconazole, cyprofuram, dichlorophene, diclobutrazole, diclofloanide, diclomezin, dichloran, dietofencarb, difenokazole, dimethymolol, dimethomorph , Diconazole, dinocap, diphenylamine, dipyrithione, ditalimfoss, dithianon, dodine, drazoxolone, edifene force, epoxyconazole, etirimole, ethriazole, phenarimol, fenbuco Nazol, fenfuram, phenytropane, fenpiclonyl, fenpropidine, fenpropormoff, fentin ah Tate, Phenyl Hydroxide, Ferbam, Perimzone, Fluazinam, Fludioxonyl, Fluoride, Fluquinconazole, Flusilazole, Flusulfamid, Plutoranyl, Flutriafol, Polpet, Pocetyl -Aluminum, phthalide, fuberidazole, furlaxyl, purmecyclox, guazintin, hexachlorobenzene, hexaconazole, hymexazole, imazaryl, imbenconazole, iminooctadine, ifprobenfos (IBP ), Iprodione, isoprothiolane, kasugamycin, copper preparations such as copper hydroxide, copper naphthenate, copper oxychloride, copper sulfate, copper oxide, auxin-copper and Bordeaux mixtures, mancopers, manco Zeb, Manev, Mepanipyrim, Mepronyl, Metallaccil, Metconazole, Metasulfocarb, Metfuroxam, Methiram, Metsulfobox, Michaelrobutanyl, Nickel Dimethyldithiocarbamate, Nitrotal Isopropyl, noir mall, opuras, oxa Dixyl, oxamocarb, oxycarboxine, pepurazoate, fenconazole, penicuron, phosphodiphene, phthalide, fimaricin, piperaline, polycarbamate, polyoxine, probenazole, prochloraz, pro Simidone, propamocarb, propiconazole, propineb, pyrazophos, pyriphenox, pyrimethanyl, pyroquilon, quintogen (PCNB), sulfur and sulfur preparations, tebuconazole, teclophthalam, Tecnazen, tetraconazole, thibendazole, thiathiophene, thiophanate-methyl, thiram, tollclofos-methyl, tolylufluoride, triadimefon, triadimenol, triazoxide, trichlamide, Tricyclazole, tridemorph, triflumizol, tripolin, triticazole, validamycin A, vinclozoline, geneb, zelam.

Salbacterase:

Bronopol, dichlorophene, nitrapyrin, nickel dimethyldithiocarbamate, kasugamycin, octylinone, furancarboxylic acid, oxytetracycline, probenazole, streptomycin, teclophthalam, copper sulfate and other copper agents.

Pesticides / Acaricides / Nematicides:

Abamectin, AC 303 630, Acetate, Acrinatrin, Alanicab, Aldicarb, Alphamethrin, Amitraz, Avermectin, AZ 60541, Azadirachtin, Ajinfoss A, Ajinfoss M, Azo Cyclotin, Bacillus thuringiensis, Bendiocarb, Benfuracarb, Bensultope, Betacyfluthrin, Bifenthrin, BPMC, Brofenprox, Bromophos A, Bufencarb, Bupropezin, Butocaxin, Butylpyridaben, kadusafos, carbaryl, carbofuran, carbophenothione, carbosulphan, cartop, CGA 157 419, CGA 184 699, chloretocarb, chlorethoxyphosphate, chlorfenbinfos, chlorfluazuron, chlor Mephos, chlorpyrifos, chlorpyrifos M, cis-resmethrin, clocitrin, clofenthezin, cyanophosph, cycloprothrin, cyfluthrin, cyhalothrin, cyhexatin, cypermethrin, Cyromazine, deltamethrin, Demetone-M, Demetone-S, Demetone-S-methyl, Di Pentiuron, diazinon, diclopention, dichlorboth, diclifoss, dicrotophos, diethione, diflubenzuron, dimethatoate, dimethylbinfoss, dioxation, disulfotone, ediffenfoss, emma Mectin, Espenvalate, Ethiophenecarb, Ethion, Etofenprox, Etoprophos, Etrifoam, Phenamifoss, Penazaquine, Penbutatin, Phenytrothion, Phenobucarb, Phenothiocarb , Phenoxycarb, phenpropartin, fenpyrad, fenpyroximate, pention, fenvalrate, fipronil, fluazinam, flucycloxanthone, flucitalinate, flufenoxuron, flufenprox , Fluvalinate, phonophos, formitol, phosphthiazate, fufenfenx, furathiocarb, HCH, heptenophos, hexaflumuron, hexiax, imidacloprid, isprobenfos, isazofoss , Isopenfoss, isoprocarb, isoxation, ibe Tin, lambda-cyhalothrin, lufenuron, malathion, mecarbam, mebinfos, mesulfenfos, metaldehyde, metacryphos, metamidophos, methidathione, methiocarb, methamyl, methol Carb, Milvemectin, Monoclotophos, Moxidecin, Naled, NC 184, NI 25, Nitenpyram, Ometoate, Oxamyl, Oxidemetone M, Oxidepropos, Parathion A, Parathion M, Permethrin, Pento 8, forate, posalon, posmet, phosphamdone, bombard, pyrimicab, pyrimifos M, pyrimifos A, propenophos, promecarb, propaphos, propoxur, prothiophos, Protoate, pymetrozine, pyraclophos, pyridapention, pyresmethrin, pyrethrum, pyridabene, pyrimidipene, pyripropoxyphene, quinalforce, RH 5992, salityon, cebufoss, silafluorophene , Sulfofep, sulfprophos, tebufenozide, tebufenpyrad, tebupyrimifos, te Rubenzuron, Tefluthrin, Temefos, Terbam, Terbufos, Tetrachlorbinfos, Thiaphenox, Thiodicarb, Thiopanox, Thiomethone, Tionazine, Turingiencin, Tralomethrin, Triara Ten, triazofoss, triazuron, trichlorphone, triflumuron, trimetacarb, tamidothion, XMC, xylylcarb, YI 5301/5302, zetamethrin.

Other known active compounds, such as herbicides, or mixtures with fertilizers and growth-controlling agents are also possible.

The active compounds according to the invention may also exist in their commercial preparations and in the use forms prepared from these preparations as mixtures with synergists. A synergist is a compound that increases the action of the active compound without the synergist itself being added need to be active.

The active compound content of the use forms prepared from the commercial formulations can vary widely. The concentration of the active compound of the use form is 0.0000001 to 95% by weight, preferably 0.0001 to 1% by weight.

The compound is used in a conventional manner suitable for the use form.

When used in hygienic pests and stored pests, the active compounds show excellent residual activity against wood and clay and excellent stability against alkalis on the lime surface.

The active compounds according to the invention are not only active against plant, sanitary and stored pests, but also in the field of veterinary medicine, for example, animal parasites (in vitro parasites), for example hard mites, soft mites, scabies mites, thrombus It is active against Trombiculid mites, flies (spit or vampires), parasitic fly larvae, teeth, hairy teeth, birds teeth and fleas. These parasites include:

Anoplurida, for example Haematopinus spp., Linognathus spp., Pediculus spp., Pthirus spp. And Soleil Sonopotes spp.

Molophagida and Amlycerina and Ischnocerina subfamily, for example Trimenon spp., Menopon spp., Trinoton spp. ), Bovicola spp., Werneckiella spp., Lepikentron spp., Damalina spp., Trichodectes spp., And Felicola spp.

Diptera and Nematotorinarina and Brachiycerina subfamily, for example Aedes spp., Anopheles spp., Culex spp., Simulium spp., Eusimulium spp., Plebotomus spp., Lutzomyia spp., Culicoides spp., Creecoides spp. Crysops spp., Hibomitra spp., Atylotus spp., Tabanus spp., Haematopota spp., Philippimia spp. (Philipomyia spp.), Braula spp., Musca spp., Hydrotaea spp., Stomoxys spp., Haematobia spp. ), Morellia spp., Pannia spp., Glossina spp., Califora spp., Lucilia spp. (Chrysomyia spp.), Olfa Wohlfartia spp., Sarcophaga spp., Oestrus spp., Hypoderma spp., Gasterophilus spp., Hippoboska Species (Hyppobosca spp.), Lipoptana spp. And Melophagus spp.

Siphonaptera, for example Pulex spp., Ctenocephalides spp., Xenopsylla spp. And Ceratophyllus spp.

The order of the Heteroptera, for example Cimex spp., Triatoma spp., Rhodnius spp. And Panstrongylus spp.

The tree of Blatarida, for example Blata orientalis, Periplaneta americana, Blata germanica and Supela spp.

Acarina (Acarida) subclass and the tree of Meta- and Mesostigmata, for example Argas spp., Ornithodorus spp., Otabius spp ., Ixodes spp., Amblyomma spp., Bophylus spp., Dermancentor spp., Haemaphysalis spp. ), Hyaloma species (Hyalomma spp.), Ripicephalus species (Rhipicephalus spp.), Dermanius species ((Dermanyssus spp.), Rilietia spp., Pneumonyssus spp. ), Sternostoma spp. And Varoa spp.

Necks of Actinedida (Prostigmata) and Acaridida (Astigmata), for example Acarapis spp., Cheiletiella spp. .), Ornithocheyletia spp., Myobia spp., Sorergates spp., Demodex spp., Trombicula spp. ), Listrophorus spp., Acarus spp., Tyrophagus spp., Caloglyphus spp., Hypodectes spp. ), Pterolichus spp., Psoroptes spp., Chorioptes spp., Otodectes spp., Sarcoptes spp. ), Notoedres spp., Knemidocoptes spp., Cytodites spp., And Laminosioptes spp. .).

The active compounds of formula (I) according to the invention can also be used in farming livestock such as cattle, sheep, goats, horses, pigs, donkeys, camels, buffaloes, rabbits, chickens, turkeys, ducks, geese, bees, and other domesticated animals. It is suitable for suppressing arthropods that infect animals, such as dogs, cats, birds in bird cages and fish tanks, and also so-called laboratory animals such as hamsters, guinea pigs, rats and mice. By inhibiting these arthropods, deaths and yield reductions (e.g. in the production of meat, milk, wool, hides, eggs, honey) are reduced, which makes the animal more economical and convenient by using the active compounds according to the invention. Breeding is possible.

The active compounds according to the invention are in the field of veterinary administration, for example, in the form of tablets, capsules, drinks, potions, granules, pastes, cyclic agents, methods of mixing drugs into feed, enteral administration in the form of suppositories, for example parenteral administration, for example By injection (intramuscular, subcutaneous, intravenous and intraperitoneal, etc.), by the form of transplantation, by intranasal administration, for example in the form of immersion or immersion, spraying, swelling and dropping, washing and misting and It is used in a known manner by transdermal administration in the form of shaped articles containing compounds, for example in the form of necklaces, ear tags, tail marks, leg bands, tethers or indicators.

When administered to livestock, poultry, farm animals, etc., the active compound of formula (I) is directly or 100 to 10,000 times as a formulation containing 1 to 80% by weight of the active compound (e.g. powders, emulsions, flowables). It can be diluted and used as a chemical bath.

Beetles,

For example, Hylotrupes bajulus, Chlorophorus pilosis, Anobium punctatum, Xestobium rufovillosum, Ptylinus pectocor Ptilinus pecticornis, Dendrobium pertinex, Ernobius mollis, Priobium carpini, Lyctus africanus, Lictus flanicolis Lyctus planicollis, Lyctus linearis, Lyctus pubescens, Trogoxylon aequale, Minthes rugicollis, Xyleborus Species, Tryptodendron species, Apate monachus, Bostrychus capucins, Heterorobostrychus brunnes, Synoxylon species, Dinoderru Minu tooth (Dinoderus minutus)

Bee (Dermapterans),

For example, Sirex jubencus, Urocerus gigas, Urocerus gigas taignus, Urocerus augur

Termites,

For example, Kalotermes flavicollis, Cryptotermes brevis, Heterotermes indicola, Reticulitermes flavipes, Reticulitermess Reticulitermes santonensis, Reticulitermes lucifugus, Mastotermes darwiniensis, Zotermopsis nevadensis, Coptermermes formosa Coptotermes formosanus

Bristletails,

For example, Lepisma saccharina

In this context, industrial materials are understood in the sense of inanimate materials, for example, synthetic materials, glues, sizes, papers and boards, leather, wood and wood products, and paints.

Materials that should be particularly protected from the attack of insects are wood and wood products.

Wood and wood products which can be protected by the compositions according to the invention or by mixtures containing such compositions are, for example, construction wood, wooden beams, railway sleepers, bridge components, jetty, wooden vehicles. (vehicle), box, pallet, container, telephone pole, wooden sign, window or door made of wood, plywood, chipboard, connector, or wood products commonly used in house construction or furniture.

The active compounds can be used, for example, in the form of concentrates or common conventional agents, for example powders, granules, solutions, suspensions, emulsions or pastes.

The formulations mentioned are known per se, for example, the active compounds may be prepared by one or more solvents or diluents, emulsifiers, dispersants and / or binders or fixatives, water repellents, drying agents and UV stabilizers, if appropriate, colorants and pigments and It can be prepared in a manner known per se by mixing different processing aids.

Insecticidal compositions or concentrates used for protecting wood or wood materials contain active compounds according to the invention in concentrations of from 0.0001 to 95% by weight, in particular from 0.001 to 60% by weight.

The amount of the composition or concentrate used depends on the type and incidence of the insect and on the medium. The optimum application rate can in each case be determined by a series of tests. In general, however, it is sufficient to use from 0.0001 to 20% by weight, preferably from 0.001 to 10% by weight, based on the material to be protected.

Solvents and / or diluents used are organic chemical solvents or solvent mixtures and / or oily or oily organic solvents or solvent mixtures and / or polar organic chemical solvents or solvent mixtures and / or water and, if appropriate, emulsifiers and / Or wetting agent.

Organic chemical solvents which can preferably be used are oily or oily solvents having an evaporation number of at least 35 and a flash point of at least 30 ° C, preferably at least 45 ° C. Materials used as oily or oily solvents having low volatility and insoluble in water are suitable mineral oils or their aromatic fractions, or mixtures of mineral oil-containing solvents, preferably White spirit, petroleum and / or alkylbenzenes. to be.

Materials that can be usefully used are mineral oils with boiling points of 170 to 220 ° C, white spirits with boiling points of 170 to 220 ° C, spindle oils with boiling points of 250 to 350 ° C, petroleum or aromatic compounds with boiling points of 160 to 280 ° C, terpentin ( terpentine) essence and the like.

In a preferred embodiment, liquid aliphatic hydrocarbons having a boiling point of 180 to 210 ° C. or high-boiling mixtures of aromatic and aliphatic hydrocarbons having a boiling point of 180 to 220 ° C., and / or spindle oil and / or monochloronaphthalene, preferably α-mono Chloronaphthalene is used.

Low volatility organic oil phase or oil type solvents having an evaporation index of at least 35 and a flash point of at least 30 ° C., preferably at least 45 ° C., may be replaced by partially volatile or intermediate organic chemical solvents, provided that the solvent is The mixture also has an evaporation index of at least 35 and a flash point of at least 30 ° C., preferably at least 45 ° C. and the pesticide / fungicide mixture is soluble or emulsifiable to this solvent mixture.

In a preferred embodiment, some organic chemical solvents or solvent mixtures are replaced with polar aliphatic organic chemical solvents or solvent mixtures. Preferred materials used are aliphatic organic chemical solvents with hydroxyl and / or ester and / or ether groups, for example glycol ethers, esters and the like.

The organic chemical binders used within the scope of the present invention are synthetic resins and / or combined dry oils which are known per se and can be diluted with water and / or are soluble or dispersible or emulsifiable in the organic chemical solvents used, specifically the binders Acrylate resins, vinyl resins such as polyvinyl acetate, polyester resins, polycondensation or polyaddition resins, polyurethane resins, alkyd resins or modified alkyd resins, phenolic resins, hydrocarbon resins such as indene / cow It consists of or contains coumarone resins, silicone resins, dry vegetable and / or dry oils and / or physical dry binders based on natural and / or synthetic resins.

Synthetic resins used as binders may be used in the form of emulsions, suspensions or solutions. Up to 10% by weight bitumen or bituminous material may also be used as the binder. In addition, colorants, pigments, water repellents, deodorants and inhibitors or anticorrosive agents, etc., known per se can also be used.

According to the invention, the composition or concentrate preferably contains one or more alkyd resins or modified alkyd resins and / or dry vegetable oils as organic chemical binders. Preferably used according to the invention are alkyd resins having an oil content of at least 45% by weight, preferably 50 to 68% by weight.

All or some of the binders mentioned above may be replaced with fixatives (mixtures) or plasticizers (mixtures). These additives are intended to prevent volatilization and crystallization or precipitation of the active compounds. They preferably replace 0.01 to 30% of the binder (based on 100% of the binder used).

Plasticizers are phthalic acid esters such as dibutyl phthalate, dioctyl phthalate or benzylbutyl phthalate, phosphoric esters such as tributyl phosphate, adipic acid esters such as di- (2-ethylhexyl) In adipates, stearates such as butyl stearate or amyl stearate, oleates such as butyl oleate, glycerol ethers or relatively high molecular weight glycol ethers, glycerol esters and p-toluenesulfonic acid esters Is derived.

The fixative is chemically based on polyvinyl alkyl ethers such as polyvinyl methyl ether, or ketones such as benzophenone or ethylbenzophenone.

Water is also particularly suitable as solvent or diluent, if appropriate as a mixture with one or more of the above-mentioned organic chemical solvents or diluents, emulsifiers and dispersants.

Particularly effective wood protection is achieved by large scale industrial impregnation methods such as vacuum, double vacuum or pressurization methods.

If suitable, the ready-to-use composition may further contain other pesticides and, if appropriate, further one or more fungicides.

Further suitable components which can be mixed are preferably the insecticides or fungicides mentioned in WO 94/29268. The compounds mentioned in the above documents clearly belong to the reference compounds of the present application.

Particularly more preferred components that can be mixed are insecticides such as chlorpyriphos, bombardment, silafluoropin, alphamethrin, cyfluthrin, cipermethrin, deltamethrin, permethrin, imidacloprid, NI-25, Flufenoxuron, hexaflumuron and triflumuron, and fungicides, for example, ethoxyconazole, hexaconazole, azaconazole, propiconazole, tebuconazole, ciproconazole, metconazole, Imazalyl, diclofloanide, tolylufluoride, 3-iodo-2-propynylbutyl carbamate, N-octyl-isothiazolin-3-one and 4,5-dichloro-N-octylisothia Sleepin-3-one.

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

<Production example>

<Example 1>

(Process a)

A solution of 3.50 g (0.012 mol) of [4- (4-nitrophenoxy)]-phenylacetyl chloride in 20 ml of acetonitrile was charged with 15 ml of pyrimidine and thieno [2,3c] isothiazole in 50 ml of acetonitrile. Add dropwise to a solution of 1.60 g (0.01 mol) of 3-yl-amine. The mixture is stirred at 25 ° C. for 18 hours and then concentrated to dryness. The reaction mixture is taken up in water / ethyl acetate and the organic phase is washed repeatedly with 10% aqueous sodium hydroxide solution. After drying and concentration, a viscous residue is obtained which is purified by silica gel chromatography using methylene chloride / ethyl acetate (20: 1) as mobile phase.

This gives 0.24 g (20% of theory) of thieno [2,3c] isothiazol-3-yl [4- (4-nitrophenoxy)]-phenylacetylamine having a melting point of 223 ° C.

Similarly and / or according to the general manufacturing process, the following compounds of formula (I) are obtained:

^* ) in mp (° C.) or ¹ HNMR, δ ppm, d ⁶ -DMSO

<Use example>

<Example A>

Paedon Lava Exam

Solvent: Dimethylformamide 7 parts by weight

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To prepare a suitable formulation of the active compound, 1 part by weight of the active compound is mixed with the specified amount of solvent and the specified amount of emulsifier and the concentrate is diluted with water to the desired concentration.

Cabbage leaves (Brassica oleracea) are immersed in the desired active compound preparation and treated with mustard worm larvae (Phaedon cochleariae) while the leaves are moistened. .

After a certain period of time, the rate of relief is measured in%. 100% means that all the beetle larvae have been killed; 0% means that the caterpillar larvae are not killed at all.

In this test, for example, the compound of Preparation Example 2 had a 100% rescue effect after 7 days at an exemplary active compound concentration of 0.1%.

<Example B>

Spodoptera prugiferda test

Solvent: Dimethylformamide 7 parts by weight

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To prepare a suitable formulation of the active compound, 1 part by weight of the active compound is mixed with the specified amount of solvent and the specified amount of emulsifier and the concentrate is diluted with water to the desired concentration.

Cabbage leaves (Brasica oleracea) are treated by immersion in the active compound formulation of the desired concentration, and treated with the larvae of the owl moth (Spodoptera prugiferda) while moistening the leaves.

After a certain period of time, the rate of relief is measured in%. 100% means that all the larvae have been killed; 0% means that the larvae have not died at all.

In this test, for example, the compound of Preparation Example 2 had a 100% rescue effect after 7 days at an exemplary active compound concentration of 0.1%.

<Example C>

Nepotetics test

Solvent: Dimethylformamide 7 parts by weight

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To prepare a suitable formulation of the active compound, 1 part by weight of the active compound is mixed with the specified amount of solvent and the specified amount of emulsifier and the concentrate is diluted with water to the desired concentration.

Rice hair (Oryza sativa) is immersed in the active compound formulation of the desired concentration and treated with green rice leaf locust larvae (Nepotetics cactipses) while moistening the hair.

After a certain period of time, the rate of relief is measured in%. 100% means that all leaf grasshoppers have been killed; 0% means that no leaf locusts have been killed.

In this test, for example, the compound of Preparation Example 2 had a rescue effect of 100% after 6 days at an exemplary active compound concentration of 0.1%.

Claims (10)

The following novel substituted N-isothiazolyl- (thio) amides are provided: [Formula I] Where Q is a group Wherein Het represents an optionally substituted heterocycle, R represents hydrogen, alkyl, halogenoalkyl, alkoxyalkyl, alkylcarbonyl, alkyl-sulfonyl, each represents optionally substituted arylcarbonyl, arylsulfonyl or arylalkyl, or optionally substituted cycloalkyl , X represents oxygen or sulfur, Y represents optionally substituted alkylene, alkenylene, alkyleneoxy or alkenylenethio, A represents optionally substituted aryl, optionally substituted cycloalkyl, optionally substituted cycloalkenyl or optionally substituted heterocycle. The method of claim 1, Q is a group Indicates Wherein Het represents a 5- or 6-membered heterocycle having one or two heteroatoms, such as N, S and O atoms, optionally substituted one- to trisubstituted by the same or different substituents, and possible substituents are halogen, C ₁ -C ₄ - alkyl, C ₁ -C ₄ - alkoxy, fluorine, chlorine and bromine atoms, such as or a different halogen atom is 1 to 5 C ₁ -C ₄ - halogenoalkyl, C ₁ -C ₄ - alkoxy - C ₁ -C ₄ - alkyl, nitro, C ₁ -C ₄ - alkylsulfonyl, fluorine and chlorine, such as the same or different halogen atom is 1 to 5 C ₁ -C ₄ - halogenoalkyl alkylsulfonyl, and also Thiocarbamoyl, R is hydrogen, C ₁ -C ₄ - alkyl, fluorine, and the same or different halogen atoms such as chlorine atoms 1 to 5 C ₁ -C ₄ - halogenoalkyl, C ₁ -C ₄ - alkoxy -C ₁ -C ₄ -alkyl, C ₁ -C ₄ -alkyl-carbonyl, C ₁ -C ₄ -alkylsulfonyl, or possible substituents in each case halogen, nitro, cyano, C ₁ -C ₄ -alkyl, fluorine And the same or different halogen atoms such as chlorine atoms, such as C ₁ -C ₂ -halogenoalkyl, C ₁ -C ₄ -alkoxy, C ₁ -C ₄ -alkylthio, fluorine and chlorine atoms Phenylcarbonyl, phenylsulfonyl, or benzyl, optionally mono- to trisubstituted, in the phenyl ring by the same or different substituents each being C ₁ -C ₂ -halogenoalkoxy having 1 to 5 different halogen atoms, or C ₃ -C ₆ -cycloalkyl which is optionally mono- to trisubstituted by the same or different substituents selected from C ₁ -C ₄ -alkyl and halogen Indicates, X represents oxygen or sulfur, Y is C ₁ -C ₆ -alkylene, C ₁ -C ₆ -hydroxyalkylene, C ₁ -C ₄ -alkoxy-C ₁ -C ₆ -alkylene, C ₁ -C ₄ -alkylcarbonyloxy- C ₁ -C ₆ - alkylene, cyano, -C ₁ -C ₆ - alkylene, fluorine and chlorine, such as the same or different halogen atom is 1 to 5 C ₁ -C ₄ - halogenoalkyl alkylene; Equal selected from fluorine, chlorine and methyl, or one optionally by different substituents to tri substituted, C ₂ -C ₄ - alkylene, C ₁ -C ₄ - alkylene, C ₁ -C ₄ - alkylene-thio Or C ₃ -C ₆ -cycloalkyl-C ₁ -C ₄ -alkylene, A is (1) possible substituents are halogen, nitro, cyano, C ₁ -C ₁₂ - same or different halogen atoms, such as alkyl, fluorine and chlorine atoms 1 to 5 C ₁ -C ₁₂ - halogenoalkyl, C ₁ - C ₁₂ - such as alkoxy, fluorine and chlorine atoms, or different 1 to 5 halogen atoms C ₁ -C ₁₂ - halogeno alkoxy, C ₁ -C ₁₂ - alkylthio, such as fluorine and chlorine atoms, or different to halo-halogen atom is 1 to 5 C ₁ -C ₁₂ - halogeno alkylthio, C ₂ -C ₁₂ - alkenyl, fluorine, and the same or different halogen atoms such as chlorine atoms 1 to 5 C ₂ -C ₁₂ C ₃ -C ₈ -cycloalkyl, a group optionally mono- to trisubstituted by the same or different substituents selected from noalkenyl, C ₁ -C ₄ -alkyl and halogen , Phenyl optionally mono- to trisubstituted by the same or different substituents; Each halogen, nitro, cyano, thio carbamoyl, C ₁ -C ₄ - alkyl, fluorine, and the same or different halogen atoms such as chlorine atoms 1 to 5 C ₁ -C ₄ - halogenoalkyl, C ₁ - C ₄ - alkoxy, C ₁ -C ₄ - alkoxy -C ₁ -C ₄ - alkyl, fluorine and chlorine atoms and the same or different 1 to 5 halogen atoms, such as C ₁ -C ₄ - halogenoalkyl alkoxy, C ₁ - C ₁ -C ₄ -halogenoalkylthio, C ₁ -C ₄ -alkylthio-C ₁ -C ₄ -alkyl, having 1 to 5 same or different halogen atoms, such as C ₄ -alkylthio, fluorine and chlorine atoms, C ₁ -C ₄ -alkylsulfinyl-C ₁ -C ₄ -alkyl, C ₁ -C ₄ -alkylsulfonyl-C ₁ -C ₄ -alkyl, C ₁ -C ₄ -alkylsulfinyl, C ₁ -C C ₁ -C ₄ -halogenoalkylsulfonyl having 1 to 5 same or different halogen atoms such as ₄ -alkylsulfonyl, fluorine and chlorine atoms, formyl, C ₁ -C ₄ -alkylcarbonyl, C _1- C ₄ -alkoxy-carbonyl, C ₁ -C ₄ -alkoxyimino-C ₁ -C ₄ -alkyl, optionally C ₁ -C ₄ -alkyl-substituted oxadiazolyl and groups or Phenyl, phenoxy, phenylthio, benzyl, benzyloxy, pyridyloxy, pyrimidyloxy, pyrazinyloxy or pyridazinyloxy optionally substituted one- to trisubstituted by the same or different substituents selected from one of Or; (2) The possible substituents are C ₁ -C ₄ - alkyl, fluorine and chlorine, such as or different halogen atom is 1 to 5 C ₁ -C ₄ - halogenoalkyl, C ₁ -C ₄ - alkoxy, fluorine, and the same or different halogen atoms such as chlorine atoms 1 to 5 C ₁ -C ₄ - halogenoalkyl alkoxy, C ₃ -C ₈ - cycloalkyl or equal to one, optionally by different substituents to be ohchihwan C ₅ -C ₈ cycloalkenyl or C ₃ -C ₈ - cycloalkyl, and halogen, cyano, nitro, C ₁ -C ₄ - alkyl, fluorine and chlorine atoms and the same or different halogen atoms, such as 1 to 5 C ₁ -C ₄ - halogenoalkyl, C ₁ -C ₄ - alkoxy, fluorine and the like, such as a chlorine atom or different halogen atom is 1 to 5 C ₁ -C ₄ - alkoxy or equal selected from halogeno different substituents Phenyl optionally substituted by one to trisubstituted; (3) 1 to 3 heteroatoms such as N, S and O atoms, and may optionally also contain one or more CO and / or CS groups as ring members, possible substituents being halogen, nitro, cyano, C ₁ -C ₄ - alkyl, C ₁ -C ₄ - alkoxy, C ₁ -C ₄ - alkylthio, fluorine, and the same or different halogen atoms such as chlorine atoms 1 to 5 C ₁ -C ₄ - halogenoalkyl, fluorine and the same or different halogen atoms such as chlorine atoms 1 to 5 C ₁ -C ₄ - halogeno-alkoxy, fluorine, and the same or different halogen atoms such as chlorine atoms 1 to 5 C ₁ -C ₄ - halogenoalkyl Thioine to a 5- or 6-membered heterocycle optionally substituted _one- to trisubstituted by the same or different substituents, or possible substituents are halogen, nitro, cyano, C ₁ -C ₄ -alkyl, C ₁ -C ₄ -alkoxy, C ₁ -C ₄ - alkylthio, such as fluorine and chlorine atoms, or And 1 to 5 halogen atoms other personal C ₁ -C ₄ - halogenoalkyl, fluorine, and the same or different halogen atoms such as chlorine atoms 1 to 5 C ₁ -C ₄ - alkoxy halogeno, such as fluorine and chlorine atoms NH, which may be optionally mono- to trisubstituted by the same or different substituents each having the same or different halogen atoms of 1 to 5 C ₁ -C ₄ -halogenoalkylthio, which may optionally be present in the heterocycle instead of the hydrogen atom With C ₁ -C ₄ -halogenoalkyl, C ₁ -C ₄ -alkoxy or fluorine or chlorine atoms, wherein the group is 1 to 5 halogen atoms, the same or different, such as C ₁ -C ₆ -alkyl, halogen, fluorine or chlorine atoms By C ₁ -C ₆ -alkyl, C ₁ -C ₆ -alkylcarbonyl or phenylsulfonyl, which in turn is optionally substituted by C ₁ -C ₄ -halogenoalkoxy having 1 to 5 same or different halogen atoms Phenyl, which may be substituted Indicate noksi, phenylthio or benzyl or; (4) It may also contain one or more heteroatoms such as O, S or N atoms, or one or more CO groups as ring members and possible substituents are halogen, nitro, cyano, C ₁ -C ₄ -alkyl C ₁ -C ₄ -halogenoalkyl, C ₁ -C ₄ -alkoxy-C ₁ -C ₄ -alkyl, C ₁ -C ₄ -alkoxy, having 1 to 5 same or different halogen atoms, such as fluorine and chlorine atoms C ₁ -C ₄ -halogenoalkoxy, C ₁ -C ₄ -alkylthio, C ₁ -C ₄ -alkylthio, fluorine and chlorine atoms having 1 to 5 same or different halogen atoms, such as fluorine and chlorine atoms. 5 individual C ₁ -C ₄ - halogenoalkyl alkylthio, C ₁ -C ₄ - alkylsulfinyl, C ₁ -C ₄ - alkylsulfonyl, hydroxyl, mercapto, C ₁ -C ₄ - alkylcarbonyl, fluorinated And C ₁ -C ₄ -halogenoalkyl-carbonyl, C ₁ -C ₄ -alkoxy-car, having 1 to 5 same or different halogen atoms such as chlorine atoms Represent condensed di- or tricyclic radicals optionally substituted one- to five-substituted by the same or different substituents which are levonyl, in particular possible substituents on the phenyl moiety are halogen, nitro, cyano, C ₁ -C ₄ -alkyl, Same as C ₁ -C ₄ -alkoxy, C ₁ -C ₄ -alkylthio, fluorine and chlorine atoms, or the same as C ₁ -C ₄ -halogenoalkyl having 1 to 5 halogen atoms, such as fluorine and chlorine atoms C ₁ -C ₄ -halogenoalkoxy having 1 to 5 different or different halogen atoms, and the same or different C ₁ -C ₄ -halogenoalkylthio having 1 to 5 halogen atoms, such as fluorine and chlorine atoms. Phenyl, phenoxy, phenylthio or benzyl, each optionally mono- to trisubstituted by other substituents; here, R ¹ represents C ₁ -C ₄ -halogenoalkyl having 1 to 5 same or different halogen atoms, such as hydrogen, C ₁ -C ₈ -alkyl, fluorine and chlorine atoms, or halogen and C ₁ -C _4- C ₃ -C ₇ -cycloalkyl which is optionally mono- or polysubstituted by the same or different substituents selected from alkyl, or possible substituents are halogen, C ₁ -C ₄ -alkyl or C ₁ -C ₄ -alkoxy Phenyl optionally mono- to trisubstituted by the same or different substituents, R ² and R ³ are the same or different and each represents hydrogen or C ₁ -C ₄ -alkyl; Among alkyl - R ⁴ is C ₁ -C ₈ - alkyl, such as fluorine and chlorine atoms, or different halogen atoms 1 to 5 C ₁ -C ₄ - halogenoalkyl, or represents a halogen, and C ₁ -C ₄ Equal to or optionally substituted with the same or different substituents selected from C ₃ -C ₇ -cycloalkyl, or the possible substituents are halogen, C ₁ -C ₄ -alkyl or C ₁ -C ₄ -alkoxy Phenyl optionally mono- to trisubstituted by different substituents; W represents oxygen or one of the groups = N-OR ⁵ and = N-NR ⁶ R ⁷ , here, R ⁵ represents C ₁ -C ₆ -alkyl or C having 1 to 5 same or different halogen atoms such as halogen, nitro, cyano, thiocarbamoyl, C ₁ -C ₄ -alkyl, fluorine and chlorine atoms C having 1 to 5 halogen atoms, such as ₁ -C ₄ -halogenoalkyl, C ₁ -C ₄ -alkoxy, C ₁ -C ₄ -alkoxy-C ₁ -C ₄ -alkyl, fluorine and chlorine atoms ₁ -C ₄ - halogenoalkyl alkoxy, C ₁ -C ₄ - alkylthio, fluorine, and the same or different halogen atoms such as chlorine atoms 1 to 5 C ₁ -C ₄ - halogenoalkyl alkylthio, C ₁ -C ₄ -Alkylthio-C ₁ -C ₄ -alkyl, C ₁ -C ₄ -alkylsulfinyl-C ₁ -C ₄ -alkyl, C ₁ -C ₄ -alkylsulfonyl-C ₁ -C ₄ -alkyl, C ₁ -C ₄ - alkylsulfinyl, C ₁ -C ₄ - alkylsulfonyl, fluorine, and the same or different halogen atoms such as chlorine atoms 1 to 5 C ₁ -C ₄ - halogenoalkyl - sulfonyl, formyl, C ₁ -C ₄ - alkyl-carbonyl, C ₁ -C ₄ - alkoxy-carbonyl and C ₁ -C ₄ - Al Shi unexposed -C ₁ -C ₄ - alkyl or selected from the same one with each other, optionally by another substituent-to three denotes a substituted benzyl that is; R ⁶ and R ⁷ are the same or different and each represents hydrogen, C ₁ -C ₆ -alkyl or possible substituents are the same or different from each other, such as halogen, nitro, cyano, C ₁ -C ₄ -alkyl, fluorine and chlorine atoms the other halogen atom is 1 to 5 C ₁ -C ₄ - halogenoalkyl, C ₁ -C ₄ - alkoxy, or fluorine, and the same or different halogen atoms such as chlorine atoms 1 to 5 C ₁ -C ₄ - halogenoalkyl alkoxy Phenyl optionally substituted with one to three substituents by the same or different substituents The method of claim 1, Q represents one of the following groups: here, Z ¹ , Z ² and Z ³ are the same or different and each is hydrogen, chlorine, bromine, nitro, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl; CH ₂ F, CHF ₂ , CF ₃ , CH ₂ Cl, CH ₂ Br, CHClCH ₃ ; Methoxy, ethoxy, methoxymethyl or ethoxymethyl, R is hydrogen, methyl, ethyl, n- or i-propyl; Methoxymethyl, ethoxymethyl, n-propoxymethyl, n-butoxymethyl; Methyl-carbonyl, methylsulfonyl; Each represents phenylcarbonyl or benzyl or cyclopropyl, optionally mono- or di-substituted by the same or different substituents selected from fluorine, chlorine, methyl or trifluoromethyl, X represents oxygen or sulfur, Y represents one of the following groups: -CH _2- , -CH (CH ₃ )-, CH (C ₂ H ₅ )-, CH (nC ₃ H ₇ )-, -CH (iC ₃ H ₇ )-, -CH ₂ -CH ₂ -,- CH (OH)-, -CH (OCH ₃ )-, -CH (O-CO-CH ₃ )-, -CH (CN)-, -CHF-, -CHCl-, -CH-[-◁]-, -CH = CH- or -CH ₂ O-. A is (1) possible substituents are halogen, nitro, cyano, C ₁ -C ₁₂ - same or different halogen atoms, such as alkyl, fluorine and chlorine atoms 1 to 5 C ₁ -C ₁₂ - halogenoalkyl, C ₁ - C ₄ -, such as alkoxy, fluorine and chlorine atoms, or different halogen atoms 1 to 5 C ₁ -C ₄ - halogenoalkyl alkoxy, C ₁ -C ₄ - alkylthio, fluorine and chlorine atoms, such as, or different a halogen atom is 1 to 5 C ₁ -C ₄ - halogenoalkyl alkylthio, C ₂ -C ₄ - alkenyl, fluorine, and the same or different halogen atoms such as chlorine atoms 1 to 5 C ₂ -C ₄ - halogeno Noalkenil, group , Phenyl optionally mono- to trisubstituted by the same or different substituents; Each halogen, nitro, cyano, thio carbamoyl, C ₁ -C ₄ - alkyl, fluorine, and the same or different halogen atoms such as chlorine atoms 1 to 5 C ₁ -C ₄ - halogenoalkyl, C ₁ - C ₄ - alkoxy, C ₁ -C ₄ - alkoxy -C ₁ -C ₄ - alkyl, fluorine and chlorine atoms and the same or different 1 to 5 halogen atoms, such as C ₁ -C ₄ - halogenoalkyl alkoxy, C ₁ - C ₁ -C ₄ -halogenoalkylthio, C ₁ -C ₄ -alkylthio-C ₁ -C ₄ -alkyl, having 1 to 5 same or different halogen atoms, such as C ₄ -alkylthio, fluorine and chlorine atoms, C ₁ -C ₄ -alkylsulfinyl-C ₁ -C ₄ -alkyl, C ₁ -C ₄ -alkylsulfonyl-C ₁ -C ₄ -alkyl, C ₁ -C ₄ -alkylsulfinyl, C ₁ -C C ₁ -C ₄ -halogenoalkylsulfonyl having 1 to 5 same or different halogen atoms such as ₄ -alkylsulfonyl, fluorine and chlorine atoms, formyl, C ₁ -C ₄ -alkylcarbonyl, C _1- C ₄ -alkoxy-carbonyl, C ₁ -C ₄ -alkoxyimino-C ₁ -C ₂ -alkyl, optionally C ₁ -C ₂ -alkyl-substituted oxadiazol-3-yl and groups or Phenyloxy, phenylthio, benzyloxy or pyridyloxy, optionally mono- to trisubstituted by the same or different substituents selected from one of: (2) cyclopentyl, cyclohexyl, cyclophene, each optionally substituted one- to five-substituted by the same or different substituents, wherein the possible substituents are fluorine, chlorine, bromine, methyl, ethyl, isopropyl, methoxy propylene trifluoromethyl; Tenyl or cyclohexenyl; (3) suitable substituents for each case include fluorine, chlorine, nitro, cyano; Methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl; Methoxy, ethoxy, n- or i-propoxy; Methylthio; -CF ₃ , -CHF ₂ , -CH ₂ CF ₃ , -CH ₂ -CF ₂ -CHF ₂ , -CH (CF ₃ ) -CH ₃ ; _{-OCF 3, -OCHF 2, OCH 2} CF 3, -O-CH 2 -CF 2 -CF 3, -OCH 2 -CF 2 -CHF 2, -O-CH (CF 3) -CH 3; One of the following heterocycles optionally mono- or disubstituted by the same or different substituents -SCF ₃ ; Each possible by the same or different substituents, wherein the possible substituents are fluorine, chlorine, nitro, cyano, methyl, ethyl, methoxy, ethoxy, methylthio, trifluoromethyl, trifluoromethoxy or trifluoromethylthio Phenyl, phenoxy or phenylthio, mono- or disubstituted, here, R ⁸ is C ₁ -C ₄ -alkyl, in particular methyl or ethyl; C ₁ -C ₄ -alkylcarbonyl, in particular methylcarbonyl or ethylcarbonyl; Also C ₁ -C ₄ -alkyl, in particular methyl or ethyl; Halogen, in particular fluorine or chlorine; C ₁ -C ₄ -halogenoalkyl, in particular trifluoromethyl; C ₁ -C ₄ -alkoxy, in particular methoxy; And C ₁ -C ₄ -halogenoalkoxy, especially phenylsulfonyl, optionally mono- or disubstituted by the same or different substituents selected from trifluoromethoxy; (4) bound if necessary and possible substituents in each case are fluorine, chlorine, bromine, nitro, cyano; Methyl, ethyl; Methoxy, methylthio, trifluoromethyl, trifluoromethoxy or trifluoromethylthioin represents the following di- or tricyclic radicals optionally mono- to tetrasubstituted by the same or different substituents: here, R ¹ represents hydrogen, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl or is optionally substituted by the same or different substituents selected from fluorine, chlorine, bromine and methyl -To optionally substituted by the same or different substituents representing C ₃ -C ₇ -cycloalkyl or possible substituents are fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, methoxy or ethoxy Phenyl mono- to trisubstituted; R ² and R ³ are the same or different and each represents hydrogen, methyl, ethyl, n- or i-propyl, n-, i- or s- or t-butyl; R ⁴ represents methyl, ethyl, n- or i-propyl, n-, i- or s- or t-butyl, or is optionally substituted with the same or different substituents selected from fluorine, chlorine, bromine and methyl; C ₃ -C ₇ -cycloalkyl which is missubstituted (preferably mono- to trisubstituted) or possible substituents are fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, methoxy or ethoxy Phenyl optionally mono- to trisubstituted by the same or different substituents; W represents oxygen or one of the groups = N-OR ⁵ and = N-NR ⁶ R ⁷ , here, R ⁵ represents C ₁ -C ₄ -alkyl, or possible substituents are fluorine, chlorine, bromine, cyano, nitro, trifluoromethyl, trifluoromethoxy, methylthio, methylsulfinyl, methylsulfonyl, methyl Benzyl optionally substituted one- to trisubstituted by the same or different substituents which are ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy or ethoxy; R ⁶ and R ⁷ are the same or different and each represents hydrogen, C ₁ -C ₄ -alkyl, or possible substituents are fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, trifluoromethyl, methoxy or Phenyl optionally mono- to trisubstituted by the same or different substituents which are trifluoromethoxy. The method of claim 1, Q represents one of the following groups: here, Z ¹ and Z ² are the same or different and each represents hydrogen, chlorine, bromine, nitro, methyl, ethyl, methoxy or ethoxy, R represents hydrogen, methyl, ethyl, methoxymethyl, ethoxymethyl, methylcarbonyl, phenylcarbonyl or methylsulfonyl, X represents oxygen or sulfur, Y represents -CH _2- , A is a possible substituent is 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, CF ₃ , OCF ₃ , OCHF ₂ , SCF ₃ , SCCl ₂ F; CH ₂ Br, CH ₂ Cl; group Phenyl optionally mono- to trisubstituted by the same or different substituents; Also fluorine, chlorine, bromine, nitro, cyano, thiocarbamoyl, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, n-, s- or t-butoxy; Methylthio, methylthiomethyl, CF ₃ , OCF ₃ , OCHF ₂ , SCF ₃ , SCCl ₂ F; CH ₂ Br, CH ₂ Cl, methoxycarbonyl, methylsulfinyl, methylsulfonyl, trifluoromethylsulfonyl or a group Phenoxy optionally substituted with one- to three-substituted by the same or different substituents selected from among; here, R ¹ represents hydrogen, methyl or ethyl; R ² and R ³ are the same or different and each represents hydrogen or methyl; R ⁴ represents methyl or ethyl; W represents oxygen or a group = N-OR ⁵ , here, R ⁵ represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl or possible substituents are fluorine, chlorine, bromine, nitro, cyano, methyl, ethyl, methoxy or Benzyl optionally mono- to trisubstituted in the ring by the same or different substituents which are ethoxy. A process for preparing a compound of formula I according to claim 1 characterized by the following steps: a) when the aminoisothiazole of formula (II) is reacted with an acyl halide of formula (III) in the presence of a base and in the presence of a diluent, to obtain a new substituted N-isothiazolyl-amide of formula (Ia); b) when reacting the N-isothiazolyl-amide of formula (Ia) obtained in process (a) with a sulfiding agent in the presence of a diluent, if appropriate, to obtain a new substituted N-isothiazolyl-thioamide of formula (Ib) ; c) When the aminoisothiazole of formula (II) is reacted with the dithioester of formula (IV) in the presence of a diluent if appropriate, a new substituted N-isothiazolyl-thioamide of formula (Ib) is also obtained: Formula Ia Formula Ib [Formula II] [Formula III] Hal-CO-Y-A [Formula IV] Where Q, R, Y and A are as defined above, respectively. Hal stands for halogen, Alk represents alkyl or group MO-CO-CH _2- , where M represents an alkali metal (such as sodium or potassium). A pesticide containing at least one compound of formula (I) as defined in claim 1. Use of a compound of formula I of claim 1 to combat pests. A method of extinguishing a pest characterized in that the compound of formula (I) of claim 1 is applied to pests and / or their habitats. A process for the preparation of agrochemicals, characterized in that the compound of formula (I) is mixed with extenders and / or surfactants. Use of a compound of formula (I) as claimed in claim 1 for the manufacture of pesticides.