CN1232464A - Substd. N-isothiazolyl-(thio) amides - Google Patents

Abstract

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 disclosed are several processes for preparing the same and their use for controlling animal pests.

Description

Substituted N-isothiazolyl-(thio)amides

The present invention relates to novel N-isothiazolyl-(thio)amides, various processes for their preparation, and their use for controlling animal pests.

Certain N-isothiazolylamide derivatives are known to have insecticidal properties (see, for example EP-A-0623282 and WO-A95/31448).

However, the efficacy and/or duration of action of these prior art compounds, especially against certain microorganisms or at low application concentrations, is not always completely satisfactory in all fields of use.

其中Het代表任选被取代的杂环，R代表氢，烷基，卤代烷基，烷氧基烷基，烷基羰基，烷基磺酰基，各自任选被取代的芳基羰基，芳基磺酰基或芳基烷基，或者代表任选被取代的环烷基，X代表氧或硫，Y代表任选被取代的亚烷基，亚链烯基，亚烷基氧基或亚烷基硫基，和A代表任选被取代的芳基，任选被取代的环烷基，任选被取代的环链烯基或者任选被取代的杂环。Therefore, the present invention provides new substituted N-isothiazolyl-(thio)amides of formula (I) where Q represents the group

wherein Het represents an optionally substituted heterocyclic ring, R represents hydrogen, alkyl, haloalkyl, alkoxyalkyl, alkylcarbonyl, alkylsulfonyl, each optionally substituted arylcarbonyl, arylsulfonyl Or arylalkyl, or represent optionally substituted cycloalkyl, X represents oxygen or sulfur, Y represents optionally substituted alkylene, alkenylene, alkyleneoxy or alkylenethio , and A represents optionally substituted aryl, optionally substituted cycloalkyl, optionally substituted cycloalkenyl or optionally substituted heterocycle.

其中Q和R各自如上定义，It has also been found that a) when an aminoisothiazole of formula (II) is reacted with an acid halide of formula (III) in the presence of a base and in the presence of a diluent, a substituted N-isothiazolyl- Amide wherein Q, R, Y and A are each as defined above,

wherein Q and R are each as defined above,

其中Q,R,Y和A各自如上定义，

其中Q,R,Y和A各自如上定义；和c)如果适当在稀释剂存在下，当式(Ⅱ)的氨基异噻唑与式(Ⅳ)的二硫酯反应时，也得到式(Ⅰb)的取代的N-异噻唑基-硫代酰胺

其中Q,R,Y和A各自如上定义，

其中Q和R各自如上定义，其中Y和A各自如上定义，和Alk代表烷基或基团MO-CO-CH₂-，其中M代表碱金属(例如钠或钾)。Hal-CO-YA (III) wherein Y and A are each as defined above, and Hal represents halogen, and b) if appropriate in the presence of a diluent, when N-isothiazolyl of formula (Ia) obtained by method (a) - When the amide is reacted with a sulfurizing reagent, the substituted N-isothiazolyl-thioamides of formula (Ib) are obtained

wherein Q, R, Y and A are each as defined above,

wherein Q, R, Y and A are each as defined above; and c) if appropriate in the presence of a diluent, when an aminoisothiazole of formula (II) is reacted with a dithioester of formula (IV), formula (Ib) is also obtained Substituted N-isothiazolyl-thioamides

wherein Q, R, Y and A are each as defined above,

wherein Q and R are each as defined above, wherein Y and A are each as defined above, and Alk represents an alkyl group or the group MO-CO- _CH2- , wherein M represents an alkali metal (eg sodium or potassium).

It has also been found that the novel substituted N-isothiazolyl-(thio)amides of the formula (I) are very suitable for controlling animal pests, in particular insects encountered in agriculture, forestry, protection of stored goods and materials and hygiene, the class Arachnida and nematodes.

其中Het代表具有1或2个杂原子，例如N,S和O原子，任选被相同或不同的取代基一至三取代的5-或6-元杂环，可能的取代基是卤素，C₁-C₄-烷基，C₁-C₄-烷氧基，具有1-5个相同或不同的卤原子例如氟，氯和溴原子的C₁-C₄-卤代烷基，C₁-C₄-烷氧基-C₁-C₄-烷基，硝基，C₁-C₄-烷基-磺酰基，具有1-5个相同或不同的卤原子例如氟和氯原子的C₁-C₄-卤代烷基磺酰基，以及硫代氨基甲酰基。R优选代表氢，C₁-C₄-烷基，具有1-5个相同或不同的卤原子例如氟和氯原子的C₁-C₄-卤代烷基，C₁-C₄-烷氧基-C₁-C₄-烷基，C₁-C₄-烷基-羰基，C₁-C₄-烷基-磺酰基，代表苯基羰基，苯基-磺酰基或苄基，其各自任选在苯基环上被相同或不同的取代基一至三取代，可能的取代基在各种情况下是卤素，硝基，氰基，C₁-C₄-烷基，具有1-5个相同或不同的卤原子例如氟和氯原子的C₁-C₂-卤代烷基，C₁-C₄-烷氧基，C₁-C₄-烷硫基，具有1-5个相同或不同的卤原子例如氟和氯原子的C₁-C₂-卤代烷氧基，或具有1-5个相同或不同的卤原子例如氟和氯原子的C₁-C₂-卤代烷硫基，或者代表任选被相同或不同的选自C₁-C₄-烷基和卤素的取代基一至三取代的C₃-C₆-环烷基。X优选代表氧或硫。Y优选代表C₁-C₆-亚烷基，C₁-C₆-羟基亚烷基，C₁-C₄-烷氧基-C₁-C₆-亚烷基，C₁-C₄-烷基羰基氧基-C₁-C₆-亚烷基，氰基-C₁-C₆-亚烷基，具有1-5个相同或不同的卤原子例如氟和氯原子的C₁-C₄-卤代亚烷基；任选被相同或不同的选自氟，氯和甲基的取代基一至三取代的C₃-C₆-环烷基-C₁-C₄-亚烷基，C₂-C₄-亚链烯基，C₁-C₄-亚烷基氧基或C₁-C₄-亚烷基硫基。A优选地Preferred substituents and/or ranges of the groups shown in the structural formulas mentioned above and below are described in detail below: Q preferably represents the group

where Het represents a 5- or 6-membered heterocycle having 1 or 2 heteroatoms, such as N, S and O atoms, optionally substituted one to three times by the same or different substituents, possible substituents being halogen, C ₁ -C ₄ -Alkyl, C ₁ -C 4 -Alkoxy, _C 1 -C ₄ -Haloalkyl, C _{1 -C 4} having 1 to 5 identical or different halogen atoms such as fluorine, chlorine and bromine atoms -alkoxy-C ₁ -C ₄ -alkyl, nitro, C ₁ -C ₄ -alkyl-sulfonyl, C ₁ -C with 1 to 5 identical or different halogen atoms such as fluorine and chlorine atoms ₄ -haloalkylsulfonyl, and thiocarbamoyl. R preferably represents hydrogen, C ₁ -C ₄ -alkyl, C ₁ -C ₄ -haloalkyl with 1 to 5 identical or different halogen atoms such as fluorine and chlorine atoms, C ₁ -C ₄ -alkoxy- C ₁ -C ₄ -Alkyl, C ₁ -C ₄ -Alkyl-carbonyl, C ₁ -C ₄ -Alkyl-sulfonyl, represents phenylcarbonyl, phenyl-sulfonyl or benzyl, each of which is optionally One to three substitutions on the phenyl ring by identical or different substituents, possible substituents are in each case halogen, nitro, cyano, C ₁ -C ₄ -alkyl, with 1 to 5 identical or C ₁ -C ₂ -haloalkyl, C ₁ -C ₄ -alkoxy, C ₁ -C ₄ -alkylthio of different halogen atoms such as fluorine and chlorine atoms, with 1 to 5 identical or different halogen atoms For example C ₁ -C ₂ -halogenated alkoxy of fluorine and chlorine atoms, or C ₁ -C ₂ -halogenated alkylthio having 1 to 5 identical or different halogen atoms such as fluorine and chlorine atoms, or representing optionally identical or different substituents selected from C ₁ -C ₄ -alkyl and halogen mono- to trisubstituted C ₃ -C ₆ -cycloalkyl. X preferably represents oxygen or sulfur. Y preferably represents 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, C ₁ -C with 1 to 5 identical or different halogen atoms such as fluorine and chlorine atoms ₄ -haloalkylene; C ₃ -C ₆ -cycloalkyl-C ₁ -C ₄ -alkylene optionally mono- to trisubstituted by identical or different substituents selected from fluorine, chlorine and methyl, C ₂ -C ₄ -alkenylene, C ₁ -C ₄ -alkyleneoxy or C ₁ -C ₄ -alkylenethio. A preferably

以及苯基，苯氧基，苯硫基，苄基，苄基氧基，吡啶基氧基，嘧啶基氧基，吡嗪基氧基或哒嗪基氧基，这些基团各自任选被相同或不同的选自下面的基团一至三取代：卤素，硝基，氰基，硫代氨基甲酰基，C₁-C₄-烷基，具有1-5个相同或不同的卤原子例如氟和氯原子的C₁-C₄-卤代烷基，C₁-C₄-烷氧基，C₁-C₄-烷氧基-C₁-C₄-烷基，具有1-5个相同或不同的卤原子例如氟和氯原子的C₁-C₄-卤代烷氧基，C₁-C₄-烷硫基，具有1-5个相同或不同的卤原子例如氟和氯原子的C₁-C₄-卤代烷硫基，C₁-C₄-烷硫基-C₁-C₄-烷基，C₁-C₄-烷基亚磺酰基-C₁-C₄-烷基，C₁-C₄-烷基磺酰基-C₁-C₄-烷基，C₁-C₄-烷基亚磺酰基，C₁-C₄-烷基磺酰基，具有1-5个相同或不同的卤原子例如氟和氯原子的C₁-C₄-卤代烷基磺酰基，甲酰基，C₁-C₄-烷基羰基，C₁-C₄-烷氧基羰基，C₁-C₄-烷氧基亚胺基-C₁-C₄-烷基，任选被C₁-C₄-烷基-取代的噁二唑基和下面的基团之一

(1) represents phenyl optionally substituted one to three times by identical or different substituents, possible substituents are: halogen, nitro, cyano, C ₁ -C ₁₂ -alkyl, with 1 to 5 identical or C ₁ -C ₁₂ -haloalkyl, C ₁ -C ₁₂ -alkoxy with different halogen atoms such as fluorine _and chlorine atoms, C 1 -C with 1 to 5 identical or different halogen atoms such as fluorine and chlorine atoms ₁₂ -Haloalkoxy, C ₁ -C ₁₂ -alkylthio, C ₁ -C ₁₂ -halogenated alkylthio with 1 to 5 identical or different halogen atoms, such as fluorine and chlorine atoms, C ₂ -C ₁₂ -chain Alkenyl, C ₁ -C ₁₂ -halogenated alkenyl having 1 to 5 identical or different halogen atoms such as fluorine and chlorine atoms, optionally replaced by identical or different halogen atoms selected from C ₁ -C ₄ -alkyl and Substituents of halogen mono- to trisubstituted C ₃ -C ₈ -cycloalkyl, the following groups

and phenyl, phenoxy, thiophenyl, benzyl, benzyloxy, pyridyloxy, pyrimidinyloxy, pyrazinyloxy or pyridazinyloxy, each of which is optionally represented by the same or different one to three substitutions selected from the following groups: halogen, nitro, cyano, thiocarbamoyl, C ₁ -C ₄ -alkyl, with 1 to 5 identical or different halogen atoms such as fluorine and C ₁ -C ₄ -haloalkyl, C ₁ -C ₄ -alkoxy, C ₁ -C ₄ -alkoxy-C ₁ -C ₄ -alkyl, having 1 to 5 identical or different C ₁ -C ₄ -haloalkoxy of halogen atoms such as fluorine and chlorine atoms, C ₁ -C ₄ -alkylthio, C 1 -C ₄ having 1 to 5 identical or different halogen atoms such as fluorine _and chlorine atoms -Haloalkylthio, 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, with 1 to 5 identical or different halogen atoms e.g. C ₁ -C ₄ -haloalkylsulfonyl, formyl, C ₁ -C ₄ -alkylcarbonyl, C ₁ -C ₄ -alkoxycarbonyl, C ₁ -C ₄ -alkoxyethylene of fluorine and chlorine atoms Amino-C ₁ -C ₄ -alkyl, optionally C ₁ -C ₄ -alkyl-substituted oxadiazolyl and one of the following groups

(2) stands for C ₅ -C ₈ -cycloalkenyl or C ₃ -C ₈ -cycloalkyl optionally substituted by one to five identical or different substituents, possible substituents being C ₁ -C ₄ -alk C ₁ -C ₄ -haloalkyl having 1 to 5 identical or different halogen atoms such as fluorine and chlorine atoms, C ₁ -C ₄ -alkoxy having 1 to 5 identical or different halogen atoms such as C ₁ -C ₄ -haloalkoxy of fluorine and chlorine atoms, C ₃ -C ₈ -cycloalkyl, and optionally identical or different ones selected from halogen, nitro, cyano, C ₁ -C ₄ -alk radical, C ₁ -C ₄ -haloalkyl having 1 to 5 identical or different halogen atoms such as fluorine and chlorine atoms, C ₁ -C ₄ -alkoxy, and having 1 to 5 identical or different halogen atoms C ₁ -C ₄ -haloalkoxy substituents such as fluorine and chlorine atoms mono- to tri-substituted phenyl;

(3) represents 1-3 heteroatoms, such as N, S and O atoms, can optionally also contain one or more CO and/or CS groups as ring members, and are optionally replaced by the same or different Substituents One to three substituted 5- or 6-membered heterocycles, possible substituents are: halogen, nitro, cyano, C ₁ -C ₄ -alkyl, C ₁ -C ₄ -alkoxy, C ₁ -C ₄ -Alkylthio, C ₁ -C ₄ -haloalkyl having 1 to 5 identical or different halogen atoms such as fluorine and chlorine atoms, having 1 to 5 identical or different halogen atoms such as fluorine and chlorine atoms C ₁ -C ₄ -haloalkoxy, C ₁ -C ₄ -haloalkoxy having 1 to 5 identical or different halogen atoms such as fluorine and chlorine atoms, or phenyl, phenoxy, phenylthio or Benzyl, each of these groups is optionally one to three substituted by identical or different substituents, possible substituents are: halogen, nitro, cyano, C ₁ -C ₄ -alkyl, C ₁ -C ₄ -alk Oxygen, C ₁ -C ₄ -alkylthio, C ₁ -C ₄ -haloalkyl having 1 to 5 identical or different halogen atoms, for example fluorine and chlorine atoms, having 1 to 5 identical or different halogen atoms For example, C ₁ -C ₄ -halogenated alkoxy of fluorine and chlorine atoms and C ₁ -C ₄ -halogenated alkylthio having 1 to 5 identical or different halogen atoms such as fluorine and chlorine atoms; and wherein optionally present in The NH group replacing a hydrogen atom in a heterocycle can be substituted by C ₁ -C ₆ -alkyl, C ₁ -C ₆ -alkylcarbonyl or phenylsulfonyl, which in turn can optionally be replaced by C ₁ -C ₆ -Alkyl, halogen, C 1 -C 4 -haloalkyl with 1 to 5 identical or different _halogen atoms _{, for example fluorine and chlorine atoms, C 1 -C 4} -alkoxy or with 1 to 5 identical or C ₁ -C ₄ -haloalkoxy substitution of different halogen atoms such as fluorine and chlorine atoms; or

(4) represents a fused compound that also contains one or more heteroatoms, such as N, S or O atoms, or one or more CO groups as ring members, and is optionally substituted by the same or different substituents from one to five Combined bi- or tricyclic groups, possible substituents are: halogen, nitro, cyano, C ₁ -C ₄ -alkyl, with 1 to 5 identical or different halogen atoms such as fluorine and chlorine atoms C ₁ -C ₄ -haloalkyl, C ₁ -C ₄ -alkoxy- _{C 1} -C ₄ -alkyl, C ₁ -C ₄ -alkoxy, with 1 to 5 identical or different halogen atoms e.g. C ₁ -C ₄ -haloalkoxy of fluorine and chlorine atoms, C ₁ -C 4 -alkylthio, C ₁ -C ₄ -haloalkylthio _having 1 to 5 identical or different halogen atoms, e.g. fluorine and chlorine atoms radical, C ₁ -C ₄ -alkylsulfinyl, C ₁ -C ₄ -alkylsulfonyl, hydroxyl, mercapto, C ₁ -C ₄ -alkylcarbonyl, with 1-5 identical or different halogen atoms For example, C ₁ -C ₄ -haloalkylcarbonyl, C ₁ -C ₄ -alkoxycarbonyl or phenyl, phenoxy, phenylthio or benzyl of fluorine and chlorine atoms, each of which is optionally represented by the same or different The substituents are one to three substituted, especially on the phenyl moiety, possible substituents are: halogen, nitro, cyano, C ₁ -C ₄ -alkyl, C ₁ -C ₄ -alkoxy, C ₁ - C ₄ -Alkylthio, C ₁ -C ₄ -haloalkyl having 1 to 5 identical or different halogen atoms such as fluorine and chlorine atoms, having 1 to 5 identical or different halogen atoms such as fluorine and chlorine atoms C ₁ -C ₄ -haloalkoxy and C ₁ -C ₄ -haloalkylthio having 1 to 5 identical or different halogen atoms, such as fluorine and chlorine atoms; wherein R ¹ represents hydrogen, C ₁ -C ₈ -alk radical, C ₁ -C ₄ -haloalkyl having 1 to 5 identical or different halogen atoms such as fluorine and chlorine atoms, represents optionally substituted by the same or different halogen and C ₁ -C ₄ -alkyl C ₃ -C ₇ -cycloalkyl substituted by one or more radicals, or represents phenyl optionally substituted one to three times by identical or different substituents, possible substituents are halogen, C ₁ -C ₄ -alkyl or C ₁ -C ₄ -alkoxy, R ² and R ³ are the same or different and each represent hydrogen or C ₁ -C ₄ -alkyl; R ⁴ represents C ₁ -C ₈ -alkyl with 1-5 C ₁ -C ₄ -haloalkyl groups of the same or different halogen atoms, such as fluorine and chlorine atoms, represent one or more substituents optionally substituted by the same or different substituents selected from halogen and C ₁ -C ₄ -alkyl C ₃ -C ₇ -cycloalkyl, or stands for phenyl optionally one to three substituted by identical or different substituents, possible substituents are halogen, C ₁ -C ₄ -alkyl or G ₁ -C ₄ - Alkoxy; and W represents one of oxygen or groups =N-OR ⁵ and =N-NR ⁶ R ⁷ , wherein R ⁵ represents C ₁ -C ₆ -alkyl or represents optionally selected from the same or different Halogen, nitro, cyano, thiocarbamoyl, C ₁ -C ₄ -alkyl, C ₁ -C ₄ -haloalkyl with 1 to 5 identical or different halogen atoms such as fluorine and chlorine atoms, C ₁ -C ₄ -alkoxy, C ₁ -C ₄ -alkoxy-C 1 -C ₄ -alkyl, C ₁ -C ₄ with 1 to 5 identical or different halogen atoms such as fluorine _and chlorine atoms -halogenated alkoxy, C ₁ -C ₄ -alkylthio, C ₁ -C ₄ -halogenated alkylthio, C ₁ -C ₄ -alkylthio having 1 to 5 identical or different halogen atoms such as fluorine and chlorine atoms -C ₁ -C ₄ -alkyl, C ₁ -C ₄ -alkylsulfinyl- _{C 1} -C 4 -alkyl, C ₁ -C ₄ -alkylsulfonyl-C ₁ -C ₄ -alk radical, C ₁ -C ₄ -alkylsulfinyl, C ₁ -C ₄ -alkylsulfonyl, C ₁ -C ₄ -haloalkyl having 1 to 5 identical or different halogen atoms such as fluorine and chlorine atoms Substitution of sulfonyl, formyl, C ₁ -C ₄ -alkylcarbonyl, C ₁ -C ₄ -alkoxycarbonyl and C ₁ -C ₄ -alkoxyimino-C ₁ -C ₄ -alkyl and R ⁶ and R ⁷ are the same or different, each represents hydrogen, C ₁ -C ₆ -alkyl or represents phenyl optionally substituted by the same or different substituents one to three times, Possible substituents are halogen, nitro, cyano, C ₁ -C ₄ -alkyl, C ₁ -C ₄ -haloalkyl with 1 to 5 identical or different halogen atoms such as fluorine and chlorine atoms, C ₁ -C ₄ -alkoxy or C ₁ -C ₄ -haloalkoxy having 1 to 5 identical or different halogen atoms, such as fluorine and chlorine atoms. Q particularly preferably represents one of the following groups wherein Z ¹ , Z ² and Z ³ are the same or different, each representing hydrogen, chlorine, bromine, nitro, methyl, ethyl, n- or iso-propyl, n-, iso-, sec- or tert -Butyl; _CH2F , _CHF2 , CF3, CH2Cl, _CH2Br , _CHClCH3 ; Methoxy _, ethoxy, methoxymethyl or ethoxymethyl _. R particularly preferably represents hydrogen, methyl, ethyl, n- or i-propyl; methoxymethyl, ethoxymethyl, n-propoxymethyl, n-butoxymethyl; methyl carbonyl, methylsulfonyl; phenylcarbonyl or benzyl, each optionally mono- or disubstituted by the same or different substituents selected from fluorine, chlorine, methyl or trifluoromethyl; or represents cyclopropyl. 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- or -CH ₂ O-.A is particularly preferred

以及苯氧基，苯硫基，苄基氧基或吡啶基氧基，这些基团各自任选被相同或不同的选自下面的取代基一至三取代：卤素，硝基，氰基，硫代氨基甲酰基，C₁-C₄-烷基，具有1-5个相同或不同的卤原子例如氟和氯原子的C₁-C₄-卤代烷基，C₁-C₄-烷氧基，C₁-C₄-烷氧基-C₁-C₄-烷基，具有1-5个相同或不同的卤原子例如氟和氯原子的C₁-C₄-卤代烷氧基，C₁-C₄-烷硫基，具有1-5个相同或不同的卤原子例如氟和氯原子的C₁-C₄-卤代烷硫基，C₁-C₄-烷硫基-C₁-C₄-烷基，C₁-C₄-烷基亚磺酰基-C₁-C₄-烷基，C₁-C₄-烷基磺酰基-C₁-C₄-烷基，C₁-C₄-烷基亚磺酰基，C₁-C₄-烷基磺酰基，具有1-5个相同或不同的卤原子例如氟和氯原子的C₁-C₄-卤代烷基磺酰基，甲酰基，C₁-C₄-烷基羰基，C₁-C₄-烷氧基羰基，C₁-C₄-烷氧基亚胺基-C₁-C₂-烷基，任选被C₁-C₂-烷基取代的噁二唑-3-基和下面的基团之一

(1) represents phenyl optionally substituted one to three times by identical or different substituents, possible substituents are: halogen, nitro, cyano, C ₁ -C ₁₂ -alkyl, with 1 to 5 identical or C ₁ -C ₁₂ -haloalkyl, C ₁ -C ₄ -alkoxy with different halogen atoms such as fluorine _and chlorine atoms, C 1 -C with 1 to 5 identical or different halogen atoms such as fluorine and chlorine atoms ₄ -Haloalkoxy, C ₁ -C ₄ -alkylthio, C ₁ -C ₄ -halogenated alkylthio with 1 to 5 identical or different halogen atoms such as fluorine and chlorine atoms, C ₂ -C ₄ -chain Alkenyl, C ₂ -C ₄ -halogenated alkenyl having 1 to 5 identical or different halogen atoms such as fluorine and chlorine atoms, the following groups

and phenoxy, phenylthio, benzyloxy or pyridyloxy, each of which is optionally substituted one to three times by the same or different substituents selected from the group consisting of halogen, nitro, cyano, thio Carbamoyl, C ₁ -C ₄ -alkyl, _{C 1 -C 4 -haloalkyl with 1 to 5 identical or different halogen atoms such as fluorine and chlorine atoms, C 1 -C 4 -alkoxy , C 1} -C ₄ -Alkoxy-C ₁ -C 4 -Alkyl _, C ₁ -C ₄ -Haloalkoxy, C ₁ -C ₄ having 1 to 5 identical or different halogen atoms, for example fluorine and chlorine atoms -Alkylthio, C 1 -C _{4 -haloalkylthio, C 1 -C 4 -alkylthio - C 1} -C ₄ -alkyl having 1 to 5 identical or different halogen atoms such as 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 -Alkyl Sulfinyl, C ₁ -C ₄ -alkylsulfonyl, C ₁ -C ₄ -haloalkylsulfonyl with 1 to 5 identical or different halogen atoms such as fluorine and chlorine atoms, formyl, C ₁ -C ₄ -Alkylcarbonyl, C ₁ -C ₄ -alkoxycarbonyl, C ₁ -C ₄ -alkoxyimino-C ₁ -C ₂ -alkyl, optionally C ₁ -C ₂ -alkyl Substituted oxadiazol-3-yl and one of the following groups

(2) represents cyclopentyl, cyclohexyl, cyclopentenyl or cyclohexenyl optionally substituted by one to five identical or different substituents, possible substituents are fluorine, chlorine, bromine, methyl, ethyl , isopropyl, methoxy or trifluoromethyl,

各种情况下合适的取代基是：氟，氯，硝基，氰基；甲基，乙基，正-或异-丙基，正-、异-、仲-或叔-丁基；甲氧基，乙氧基，正-或异-丙氧基；甲硫基；-CF₃，(3) represents the following heterocycles optionally substituted one or two by the same or different substituents:

Suitable substituents in each case are: fluorine, chlorine, nitro, cyano; methyl, ethyl, n- or i-propyl, n-, i-, sec- or tert-butyl; methoxy Base, ethoxy, n- or iso-propoxy; methylthio; -CF ₃ ,

-CHF ₂ , -CH ₂ CF ₃ , -CH ₂ -CF ₂ -CHF ₂ , -CH(CF ₃ )-CH ₃ ; -OCF ₃ ,

-OCHF ₂ ,OCH ₂ CF ₃ ,-O-CH ₂ -CF ₂ -CF ₃ ,-OCH ₂ -CF ₂ -CHF ₂ ,

-O-CH(CF ₃ )-CH ₃ ; -SCF ₃ ; and phenyl, phenoxy or phenylthio, each of these groups optionally being mono- or disubstituted with the same or different substituents, possible substituents is: fluorine, chlorine, nitro, cyano, methyl, ethyl, methoxy, ethoxy, methylthio, trifluoromethyl, trifluoromethoxy or trifluoromethylthio; wherein R ⁸ represents C ₁ -C ₄ -alkyl, in particular methyl or ethyl; C ₁ -C ₄ -alkylcarbonyl, in particular methylcarbonyl or ethylcarbonyl; and represents optionally identically or differently selected from C ₁ -C ₄ -Alkyl, especially methyl or ethyl; Halogen, especially fluorine or chlorine; C ₁ -C ₄ -Haloalkyl, especially trifluoromethyl; C ₁ -C ₄ -Alkoxy, In particular methoxy; and substituents of C ₁ -C ₄ -haloalkoxy, especially trifluoromethoxy, mono- or disubstituted phenylsulfonyl; or

各种情况下可能的取代基是：氟，氯，溴，硝基，氰基；甲基，乙基；甲氧基，甲硫基，三氟甲基，三氟甲氧基或三氟甲硫基；其中R¹代表氢，甲基，乙基，正-或异-丙基，正-、异-、仲-或叔丁基，代表任选被相同或不同的选自氟，氯，溴和甲基的取代基一至五取代的C₃-C₇-环烷基，或者代表任选被相同或不同的取代基一至三取代的苯基，可能的取代基是氟，氯，溴，甲基，乙基，正-或异-丙基，甲氧基或乙氧基，R²和R³是相同或不同的，各自代表氢，甲基，乙基，正-或异-丙基，正-、异-、仲-或叔丁基；R⁴代表甲基，乙基，正-或异-丙基，正-、异-、仲-或叔丁基，代表任选被相同或不同的选自氟，氯，溴和甲基的取代基一至五取代(优选一至三取代)的C₃-C₇-环烷基，或者代表任选被相同或不同的取代基一至三取代的苯基，可能的取代基是氟，氯，溴，甲基，乙基，正-或异-丙基，甲氧基或乙氧基；和W代表氧或基团=N-OR⁵和=N-NR⁶R⁷之一，其中R⁵代表C₁-C₄-烷基或者代表任选被相同或不同的取代基一至三取代的苄基，可能的取代基是氟，氯，溴，硝基，氰基，三氟甲基，三氟甲氧基，甲硫基，甲基亚磺酰基，甲基磺酰基，甲基，乙基，正-或异-丙基，正-、异-、仲-或叔丁基，甲氧基或乙氧基；和R⁶和R⁷是相同或不同的，各自代表氢，C₁-C₄-烷基或者代表任选被相同或不同的取代基一至三取代的苯基，可能的取代基是氟，氯，溴，硝基，氰基，甲基，乙基，三氟甲基，甲氧基或三氟甲氧基。Q非常特别优选代表下面基团之一其中Z¹和Z²是相同或不同的，各自代表氢，氯，溴，硝基，甲基，乙基，甲氧基或乙氧基。R非常特别优选代表氢，甲基，乙基，甲氧基甲基，乙氧基甲基，甲基羰基，苯基羰基或甲基磺酰基。X非常特别优选代表氧或硫。Y非常特别优选代表-CH₂-。A非常特别优选地代表任选被相同或不同的取代基一至三取代的苯基，可能的取代基是：氟，氯，溴，硝基，氰基，甲基，乙基，正-或异-丙基，正-、异-、仲-或叔丁基，甲氧基，乙氧基，正-或异-丙氧基，正-、异-、仲-或叔丁氧基；甲硫基，CF₃,OCF₃,OCHF₂,SCF₃,SCCl₂F；CH₂Br, CH₂Cl；基团

还有苯氧基，其任选被相同或不同的选自下面的取代基一至三取代：氟，氯，溴，硝基，氰基，硫代氨基甲酰基，甲基，乙基，正-或异-丙基，正-、异-、仲-或叔丁基，甲氧基，乙氧基，正-或异-丙氧基，正-、异-、仲-或叔丁氧基；甲硫基，甲硫基甲基，CF₃,OCF₃,OCHF₂,SCF₃,SCCl₂F；CH₂Br,CH₂C1，甲氧羰基，甲基亚磺酰基，甲基磺酰基，三氟甲基磺酰基或者基团

其中R¹代表氢，甲基或乙基；R²和R³是相同或不同的，各自代表氢或甲基；R⁴代表甲基或乙基；和W代表氧或基团=N-OR⁵，其中R⁵代表甲基，乙基，正-或异-丙基，正-、异-、仲-或叔丁基，或者代表在环上，任选被相同或不同的取代基一至三取代的苄基，可能的取代基是氟，氯，溴，硝基，氰基，甲基，乙基，甲氧基或乙氧基。(4) represents the following bi- or tricyclic groups which are attached as required and are optionally substituted by one to four identical or different substituents: Adamantyl

Possible substituents in each case are: fluorine, chlorine, bromine, nitro, cyano; methyl, ethyl; methoxy, methylthio, trifluoromethyl, trifluoromethoxy or trifluoromethyl Sulfuryl; Wherein R ¹ represents hydrogen, methyl, ethyl, n- or iso-propyl, n-, iso-, sec- or tert-butyl, represents optionally selected from the same or different fluorine, chlorine, C ₃ -C ₇ -cycloalkyl substituted one to five times by the substituents of bromine and methyl, or represents phenyl optionally substituted one to three times by identical or different substituents, possible substituents are fluorine, chlorine, bromine, Methyl, ethyl, n- or i-propyl, methoxy or ethoxy, ^R2 and ^R3 are the same or different, each representing hydrogen, methyl, ethyl, n- or i-propyl , n-, iso-, sec- or tert-butyl; R ⁴ represents methyl, ethyl, n- or i-propyl, n-, iso-, sec- or tert-butyl, represents optionally identical or C 3 -C 7 -Cycloalkyl groups that are one to five substituted (preferably one to three substituted) with different substituents selected from fluorine, chlorine, bromine and methyl, or represent C ₃ -C ₇ -cycloalkyl groups optionally substituted one to three times with the same or different substituents phenyl, possible substituents are fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, methoxy or ethoxy; and W represents oxygen or the group =N-OR ⁵ and = One of N-NR ⁶ R ⁷ , wherein R ⁵ represents C ₁ -C ₄ -alkyl or represents benzyl optionally substituted one to three times by identical or different substituents, possible substituents are fluorine, chlorine, bromine, Nitro, cyano, trifluoromethyl, trifluoromethoxy, methylthio, methylsulfinyl, methylsulfonyl, methyl, ethyl, n- or iso-propyl, n-, iso -, sec- or tert-butyl, methoxy or ethoxy; and R ⁶ and R ⁷ are the same or different, each representing hydrogen, C ₁ -C ₄ -alkyl or representing optionally identical or different Substituents Mono- to tri-substituted phenyl, possible substituents are fluorine, chlorine, bromine, nitro, cyano, methyl, ethyl, trifluoromethyl, methoxy or trifluoromethoxy. Q very particularly preferably represents one of the following groups wherein ^Z1 and ^Z2 are the same or different, each representing hydrogen, chlorine, bromine, nitro, methyl, ethyl, methoxy or ethoxy. 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 very particularly preferably represents phenyl optionally substituted one to three times by identical or different substituents, possible substituents are: fluorine, chlorine, bromine, nitro, cyano, methyl, ethyl, n- or iso -Propyl, n-, i-, sec- or tert-butyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, sec- or tert-butoxy; methylthio group, CF ₃ , OCF ₃ , OCHF ₂ , SCF ₃ , SCCl ₂ F; CH ₂ Br, CH ₂ Cl; group

There is also phenoxy, which is optionally substituted one to three times by the same or different substituents selected from the group consisting of fluorine, chlorine, bromine, nitro, cyano, thiocarbamoyl, methyl, ethyl, n- or i-propyl, n-, i-, sec- or tert-butyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, sec- or tert-butoxy; Methylthio, methylthiomethyl, CF ₃ , OCF ₃ , OCHF ₂ , SCF ₃ , SCCl ₂ F; CH ₂ Br, CH ₂ C1, methoxycarbonyl, methylsulfinyl, methylsulfonyl, tri Fluoromethylsulfonyl or group

wherein R ¹ represents hydrogen, methyl or ethyl; R ² and R ³ are the same or different, each representing hydrogen or methyl; R ⁴ represents methyl or ethyl; and W represents oxygen or the group =N-OR ⁵ , wherein R ⁵ represents methyl, ethyl, n- or iso-propyl, n-, iso-, sec- or tert-butyl, or represents on the ring, optionally replaced by the same or different substituents from one to three Substituted benzyl, possible substituents are fluorine, chlorine, bromine, nitro, cyano, methyl, ethyl, methoxy or ethoxy.

其中R,Z¹和Z²各自具有上述一般、优选、特别优选和非常特别优选的定义，和X¹,X²,X³,X⁴和X⁵代表上述在A下对苯基和/或苯氧基作为一般、优选、特别优选和非常特别优选的取代基定义的那些基团，和X¹,X²,X³和X⁴也可以代表氢。Preferred compounds of the present invention are compounds of formulas (IA) to (ID):

wherein R, Z ¹ and Z ² each have the above-mentioned general, preferred, particularly preferred and very particularly preferred definitions, and X ¹ , X ² , X ³ , X ⁴ and X ⁵ represent the above-mentioned p-phenyl group under A and/or Phenoxy is those radicals defined as general, preferred, particularly preferred and very particularly preferred substituents, and X ¹ , X ² , X ³ and X ⁴ may also represent hydrogen.

A further preferred group of compounds are those compounds of the formulas (IA) to (ID) in which the phenoxy group is para-positioned to the NR-CO- _CH2- or NR-CS- _CH2- group, of which particularly preferred are those compounds wherein the substituents X ¹ , X ² , X ³ and X ⁴ represent hydrogen.

The above general or preferred radical definitions or illustrations apply to the end products and correspondingly to the starting materials and intermediates. These group definitions can be combined with each other as required, ie combinations between the respective preferred ranges are also included.

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

Particular preference according to the invention is given to compounds of the formula (I) in which the combination of the definitions mentioned above is contained as particularly preferred.

Very particularly preferred according to the invention are compounds of the formula (I) which are contained as very particularly preferred combinations of the definitions mentioned above.

In the radical definitions given above and below, hydrocarbyl groups such as alkyl or alkenyl - also in combination with heteroatoms, such as alkoxy or alkylthio - are in each case whenever possible The chain can be linear or branched.

R=HX=OY=CH₂A=如下所列：表2表2包括通式(Ⅰ)化合物，其中Y=CH(CH₃)Q,R,X和A=如表1所列。表3表3包括通式(Ⅰ)化合物，其中

R,X,Y和A=如表1所列。表4表4包括通式(Ⅰ)化合物，其中X=SQ,R,Y和A=如表3所列。表5表5包括通式(Ⅰ)化合物，其中

R,X,Y和A=如表1所列。表6表6包括通式(Ⅰ)化合物，其中R,X,Y和A=如表1所列。表7表7包括通式(Ⅰ)化合物，其中R,X,Y和A=如表1所列。表8表8包括通式(Ⅰ)化合物，其中R=HX    =    OY    =    CH₂A    =    

Q    =    如下所列：

表9表9包括通式(Ⅰ)化合物，其中 Listed in Tables 1 to 9 are examples of new substituted N-isothiazolyl-(thio)amides: The compound of table 1 corresponds to the compound of general formula (I), wherein

R=HX=OY=CH ₂ A= as listed below: Table 2 Table 2 includes compounds of general formula (I), wherein Y=CH(CH ₃ )Q, R, X and A=as listed in Table 1. Table 3 Table 3 includes compounds of general formula (I), wherein

R, X, Y and A= as listed in Table 1. Table 4 Table 4 includes compounds of general formula (I), wherein X=SQ, R, Y and A=as listed in Table 3. Table 5 Table 5 includes compounds of general formula (I), wherein

R, X, Y and A= as listed in Table 1. Table 6 Table 6 includes compounds of general formula (I), wherein R, X, Y and A= as listed in Table 1. Table 7 Table 7 includes compounds of general formula (I), wherein R, X, Y and A= as listed in Table 1. Table 8 Table 8 includes compounds of general formula (I), wherein R=HX=OY=CH ₂ A=

Q = as listed below:

Table 9 Table 9 includes compounds of general formula (I), wherein

Q, R, X and Y= as listed in Table 8.

In the preparation of compounds of formula (Ia) according to method (a), using, for example, thieno[2,3c]isothiazol-3-yl-amine and [4-(4-cyanophenoxy)]-phenyl- Acetyl chloride is starting material, then reaction process can be represented by following reaction formula:

In the preparation of compounds of formula (Ib) according to method (b) using, for example, thieno[2,3c]isothiazol-3-yl-[4-(4-nitrophenoxy)]-phenyl-acetamide as the starting material, and Lawesson's reagent (2,4-bis-(4-methoxyphenyl)-1,3-dithia-2,4-diphosphetan-2,4-disulfide) as the vulcanizing agent , the reaction process can be expressed by the following reaction formula:

In the preparation of compounds of formula (Ib) according to process (c), using for example thieno[2,3c]isothiazol-3-yl-amine and [4-(4-chlorophenoxy)]-phenyl- Methyl dithioacetate is initiator, then reaction process can be represented by following reaction formula:

The aminoisothiazoles of the formula (II) required as starting materials in the processes (a) and (c) of the present invention are known (see, for example GB1568377; J.Chem.Res.Synop.1989,29; DE-A2713573 ; Can.J.Chem.1973(51), 1742 or JP05070469) and/or can be prepared by known methods (see, for example, the aforementioned references).

其中Het如上定义，并且接着用氧化剂例如H₂O₂、溴或次氯酸钠氧化得到的式(Ⅵ)硫代酰胺衍生物其中Het如上定义。They can also be prepared, for example, by first reacting an aminonitrile derivative of formula (V) with hydrogen sulfide in the presence of a base such as pyridine or triethylamine,

wherein Het is as defined above, and then oxidized with an oxidizing agent such as H ₂ O ₂ , bromine or sodium hypochlorite to obtain a thioamide derivative of formula (VI) wherein Het is as defined above.

Aminonitrile derivatives of formula (V) are known (see, for example, EP-A0453611; ActaChim.Scand., Ser.B.1975, B29(2), 224; DE-A2713573; Bulletin of Medicinal Chemistry (Chem. Pharm.Bull.) 1971,19,119; Tetrahedron Communications, 1989,30,2631; J.Chem.Soc., Perkins Trans I, 1987,1521; Helv.Chim.Acta1975,58,2192; Journal of Medicinal Chemistry (J. Med.Chem.) 1987,30,91; Journal of Heterocyclic Chemistry (J.Het.Chem.) 1985,22,1093 or EP-A0636626), and/or it can be prepared by known methods (see, for example, references above).

The acid halides of the formula (III) which are also used as starting materials in the 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 formula (IV) which are also used as starting materials in process (c) of the present invention are known (see, for example, Tetrahedron 2663 (1984) or J.Chem.Research (M. ) 2701 (1988)), and/or it can be prepared by similar known methods. In formula (IV), Alk preferably represents methyl.

Preferred diluents for carrying out the 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, ether or acetonitrile.

Suitable bases for carrying out process (a) 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 nitrogen bases. Examples that may be mentioned are sodium hydroxide, calcium hydroxide, potassium carbonate, sodium bicarbonate, triethylamine, dibenzylamine, diisopropylamine, pyridine, quinoline, diazabicyclooctane (DABCO) , diazabicyclononene (DBN) and diazabicycloundecene (DBU).

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

When carrying out process (a), generally 1 to 2 moles, preferably 1 to 1.5 moles, of acid halides of formula (III) are used per mole of aminoisothiazole of formula (II).

In some cases it is advantageous to use the aminoisothiazoles of the formula (II) in the form of their hydrohalide salts, for example, especially the hydrochloride salts.

The preferred vulcanizing agent for carrying out the method (b) of the present invention is: phosphorus pentasulfide or Lawesson's reagent [2,4-bis-(4-methoxy-phenyl)-1,3,2,4-dithia diphosphetan-2, 4-dithione] (referring to, tetrahedron, Vol.41, No.22,5061 ff (1985)).

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

When carrying out the process (b) 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 between 0°C and +200°C, preferably between 20°C and 150°C.

When carrying out process (b), generally 1-3 moles, preferably 1-2 moles of vulcanizing agent are used per mole of compound of formula (Ia). Post-processing is carried out by conventional methods.

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

However, it is also possible to carry out the reaction neat without any solvent.

When carrying out the 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 between 0°C and +150°C, preferably between 20°C and 120°C.

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

The active compounds according to the invention which have good crop tolerance and low toxicity to warm-blooded animals are suitable for controlling animal pests, in particular insects, arachnids, Classes and nematodes. They are preferably used as crop protection agents. These compounds are active against generally sensitive and resistant species and are effective at all or some stages of pest development. The aforementioned pests include: from the order of the Isopoda, for example Oniscus aselluse, Armadillidium vulgare and Porcellio scaber. From the order Diplopoda, eg Blaniulus gutttulatus. From the suborder of the Chilopoda, for example, Geophilus carpophagus and Scutigera spec. Synphyla, eg Scutigerella immaculata. From the order of the Thysanura, eg, the silverfish (Lepisma saccharina). From the order of the Collembola, eg Onychiurus armatus. From the order of Orthoptera, such as Blatta orientalis, Periplaneta americana, Leucophaea maderae, Blattella germanica, Acheta domesticus, mole crickets Genus (Gryllotalpa spp.), Locusta migratoria migratioides, Melanoplus differentialis and Schistocerca gregaria. From the order of the Dermaptera, for example Forficula auricularia. From the order of the Isoptera, for example, Reticulitermes spp. From the order of the lice (Anoplura), for example head lice (Pediculus humanus corporis), blind lice (Haematopinus spp.) and long-fronted lice (Linognathus spp.). From the order of the Mallophaga, for example Trichodectes spp. and Damalinea spp. From the order of the Thysanoptera, for example, Hercinothrips femoralis and Thrips tabaci . From the suborder of the Heteroptera, for example Eurygasters pp., Dysdercus intermedius, Piesma quadrata, Cimex lectularius, Rhodnius prolixus and Triatoma spp. Homoptera, such as Aleurodes brassicae, cotton whitefly (Bemisiatabaci), greenhouse whitefly (Trialeurodes vaporariorum), cotton aphid (Aphisgossypii), cabbage aphid (Brevicoryne brassicae), tea deer aphid (Cryptomyzus ribis) , Aphis fabae, Aphispomi, Eriosoma lanigerum, Hyalopterus arundinis, Phyloxera vastatrix, Pemphigus spp., Macrosiphumavenae, Myzus spp., Hubu Phorodon humuli, Rhopasiphum padi, Empoasca spp., Euscelis bilobatus, Nephotettix cincticeps, Lecanium corni, Saissetia oleae ), rice brown planthopper (Laodelphax striatellus), brown rice hopper (Nilaparvata lugens), red round scale (Aonidiella aurantii), Aspidiotus hederae, mealybug genus (Pseudococcus spp.) and psyllid genus (Psylla spp.). From the order of Lepidoptera, e.g., pink bollworm (Pectinophora gossypiella), pine looper (Bupalus piniarius), Cheimatobia brumata, Lithocolletis blancardella, cherry nest moth (Hyponomeuta padella), diamondback moth (Plutella maculipennis), canopy caterpillar (Malacosomaneustria) , Euproctis chrysorrhoea, Lymantria spp., Bucculatrix thurberiella, Phyllocnisticitrella, Cutworm (Agrotis spp.), Cutworm (Euxoa spp.), Brown Spodoptera (Feltia spp.), Egyptian Diamondhead (Earias insulana), Spodoptera (Heliothis spp.), Beet Spodoptera (Spodoptera exigua), Cabbage Spodoptera (Mamestrabrassicae), Panolis flammea, Spodoptera litura, Spodoptera spp., Trichoplusia ni, Carpocapsa pomonella, Pieris spp., Chilospp., Pyrausta nubilalis, Ephestia kuehniella, Galleria mellonella, Tineola bisselliella ), Tinea pellionella, Hofmannophilapseudospretella, Cacoecia podana, Capua reticulana, Choristoneura fumiferana, Clysia ambiguella, Homona magnanima and Oak green Leaf tortrix (Tortrix viridana). From the order of the Coleoptera, e.g., Anobium punctatum, Rhizopertha dominica, Bruchidius obtectus, soybean elephant (Acanthoscelides obtectus), house beetle (Hylotrupes bajulus), Agelastica alni, beetle beetle (Leptinotarsa decemlineata), Phaedon cochleariae, Diabrotica spp., Psylliodes chrysocephala, Epilachnavarivestis, Atomaria spp., Oryzaephilussurinamens, Anthonomus spp., rice Sitophilus spp., Otiorrhynchus sulcatus, Cosmopolitessordidus, Ceuthorrhynchus assimilis, Hyperaposttica, Dermestes spp., Trogoderma spp., Dermestes (Anthrenus spp.), black beetle (Attagenue spp.), powder beetle (Lyctus spp.), Meligethes aeneus, spider beetle (Ptinus spp.), golden spider beetle (Niptus hdoleucus), wheat spider beetle (Gibbium psylliodes), Tribolium spp., Tenebrio molitor, Agriotesspp., Conoderus spp., Mellontha meiolontha, Amphimallon solstitialis and Costelytra zealandica. Hymenoptera, for example, Diprion spp., Hoplocampa app., Lasius spp., Monomorium pharaonis, and Vespa spp. Diptera, for example, Aedes spp., Anopheless pp., Culex spp., Drosophila melanogaster, Musca spp. , Stable fly (Fannia spp.), Red-headed blowfly (Calliphoraerythrocephala), Lucilia spp., Chrysomyia spp., Cuterebra spp., Gastrophilus spp., Hyppobosca spp., Sting flies ( Stomoxys spp.), Oestrus spp., Hydodermaspp., Tabanus spp., Tannia spp., Bibio hortulanus, Oscinella frit, Phorbia spp.), Pegomyia hyoscyami, Ceratitis capitata, Dacus oleae and Tipulapaludosa. From the order of the Siphonaptera, for example, Xenopsylla cheopis , and Ceratophyllus spp. Arachnida, eg Sciopio maurus, Latrodectus mactans. From the order of the Acarina, for example, Acarus siro, Argasspp., Ornithodoros spp., Dermanyssus gallinae, Eriophyes ribis, Phyllocoptruta oleivora), Boophilus spp., Rhipicephalus spp., Amblyomma spp., Hyalomma spp., Ixodes spp., Psoroptes spp. , Chigger mite (Chorioptes spp.), Scabies mite (Sarcoptess pp.), Line mite (Tarsonemus spp.), Cliff mite (Bryobia praetiosa), red spider mite (Panonychus spp.), and red spider mite (Tetranychus spp. .).

Parasitic plant nematodes include, for example, Pratylenchus spp., Radopholus similis, Ditylenchus dipsaci, Tylenchulus semipenetrans, Heterodera spp. , Globoders spp., Meloidogyne spp., Aphelenchoides spp., Longidorus spp., Xiphinema spp. , Trichodorus spp.

The compounds of the formula (I) according to the invention have particularly excellent insecticidal activity.

They are used particularly successfully against pests that injure plants and are highly active, for example against horseradish beetle (Phaedon cochleariae) larvae, grass armyworm (Spodoptera frugiperda) caterpillars and black-tailed leafhopper (Nephotettix cincticeps).

The active compounds can be converted into customary preparations, for example solutions, emulsions, wettable powders, suspensions, dusts, fine powders, pastes, soluble powders, granules, suspoemulsions, natural and synthetic materials impregnated with active compounds, and microscopic capsules encapsulated in polymers.

These formulations can be produced in known manner, for example and preferably by mixing the active compounds with extenders, i.e. liquid solvents and/or solid carriers, and optionally using surfactants, i.e. emulsifiers and/or dispersants and/or Foaming agent.

If water is used as extender, it is also possible to use, for example, organic solvents as auxiliary solvents. Suitable liquid solvents mainly include: aromatic compounds, such as xylene, toluene or alkylnaphthalene, chlorinated aromatic compounds and chlorinated aliphatic hydrocarbons, such as chlorobenzenes, vinyl chloride or methylene chloride, aliphatic hydrocarbons, such as cyclo Hexane or paraffins such as mineral oil fractions, mineral and vegetable oils, alcohols such as butanol or glycol and their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone , strong polar solvents such as dimethylformamide and dimethylsulfoxide, and water.

Suitable solid carriers are:

eg ammonium salts, 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 broken natural minerals such as calcite, marble, pumice, sepiolite and dolomite, and synthetic granules of organic and inorganic powders, and organic particles 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 alcohols Ethers, e.g., alkyl aryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates and protein hydrolysates; suitable dispersants are: e.g. lignosulfurous acid waste liquor and Methylcellulose.

In formulations, binders such as carboxymethylcellulose and natural and synthetic polymers in powder, granular or latex form, such as gum arabic, polyvinyl alcohol and polyvinyl acetate, and natural phospholipids such as cephalin and egg Phospholipids, and synthetic phospholipids. Other possible additives may be mineral and vegetable oils.

Dyes such as inorganic pigments such as iron oxide, titanium oxide and Prussian blue, and organic dyes such as alizarin dyes, azo dyes and metal phthalocyanine dyes, and micronutrients such as iron, manganese, boron, copper, cobalt can also be used , molybdenum and zinc salts.

In general, the preparations contain 0.1-95% by weight of active compound, preferably 0.5-90%.

The active compounds according to the invention can be present in their commercial formulations and in the use forms prepared from these formulations as a mixture with other active compounds, for example insecticides, attractants, sterilants, bactericides, acaricides, nematocides, Fungicides, growth regulators or herbicides. Pesticides include, for example, phosphates, carbamates, carboxylates, chlorinated hydrocarbons, phenylureas and compounds produced by microorganisms.

Particularly useful hybrids are, for example, those listed below:

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-methoxy Amino-N-methyl-2-(2-phenoxyphenyl)-acetamide; 8-hydroxyquinoline sulfate; (E)-2-{2-[6-(2-cyanophenoxy Base)-pyrimidin-4-yloxy]-phenyl}-3-methoxymethyl acrylate; (E)-methoxyimino[α-(o-tolyloxy)-o-tolyl] Methyl acetate; 2-Phenylphenol (OPP), aldimorph, amalate, difenazol, penconazole,

Benalaxyl, o-iodoanilide, benomyl, Lexa, biphenyl, bisbenzotriazole, blasticidin, furconazole, pyrimethrin sulfonate, Dingsaite,

Lime sulfur mixture, captendan, captan, carbendazim, wiltazol, mitemeng, dimaosan, chloropicrin, chlorothalonil, acetonil, maneb, cream urine cyanide, cyclazole Alcohol, Eclostrobin,

Diclofenac, clotriazole, diclofluanid, pyridoxine, clonamide, dimethocarb, difenoconazole, pyrimidine, dimethomorph, diniconazole, dinitrocrotonate, diphenylamine , pyridil, fenphos, dithianon, dodine, amoxazolone,

Kewensan, epoxyconazole, pyrimethrimol, terendazim,

Chlorpyrimidinol, fenbuconazole, tofuranilide, seed coating ester, seed dressing, fenpropidin, fenpropimorph, triphenyltin acetate, triphenyltin hydroxide, ferbam, pyrizone, fluorine Acetinamine, fludioxonil, fludioxonil, fluquinconazole, flusilazole, sulfanil, flunamide, fuconazole, folpet, ethylfosmoluminum, tetrachlorophthalide, wheat suingin, furaxyl, mixed Kind of amine, Guzhongding,

Hexachlorobenzene, Hexaconazole, Hymexazol,

Imazalil, Amidazole, Bivalve Acetate, Isoblastin (IBP), Iprodione, Indazol,

Kasugamycin, copper preparations such as: copper hydroxide, copper naphthenate, copper oxychloride, copper sulfate, copper oxide, copper 8-hydroxyquinoline and Bordeaux mixture,

Mancocopper, Maneb, Mancozeb, Azoxystrobin, Rustamine, Metalaxyl, Metconazole, Sulfurcarbacarb, Fufenamide, Dysenlian, Thiafil, Myclobutanil,

Nickel dimethyl dithiocarbamate, nitrotha]-isopropyl, fluoropyrimol,

Formofuramide, oxaxyl, oxamocarb, oxidized carboxyl,

Rice blastate ester, penconazole, pentilon, rice blast phosphorus, tetrachlorophthalide, domomycin, sick flower spirit, polyurethane, polyoxin, enpyridazole, mixianan, procymidone, propionamide, cyproconazole, propineb, pyrafos, pyrimandroxime, pyrimethanil, pyroquinone,

Pentachloronitrobenzene (PCNB),

Sulfur and sulfur preparations,

Tebuconazole, Yekuphthalein, Tetrachloronitrobenzene, Fluoximazole, Thiabendazole, Thipronil, Thiophanate-Methyl, Thiram, Tolclofos-Methyl, Methyl Fluorosulfonamide, Triadimefon, Triaconazole, pyraclostrobin, salicilamine, tricyclazole, tridemorph, fluconazole, pyrazine, triticonazole,

Rice pattern powder, vinylcleanthin,

Zinc, zirdine.

Bactericides:

bronopol, dichlorophen, chloromethylpyridine, nickel dimethyldithiocarbamate, kasugamycin, isothiazolones, furancarboxylic acid, oxytetracycline, enisoprothiazole, streptomycin, eocumin, copper sulfate and Other copper preparations.

Insecticides/Acaricides/Nematocides:

Abamectin, AC303630, acephate, fluatethrin, acetaminocarb, aldicarb, alpha-cypermethrin, amphetamine, avermectin, AZ60541, azadirachtin, azinphos-A, acetophos, Triazolidine,

Bacillus thuringiensis, bentoxacarb, carbofuran, dimethia, cyfluthrin, bifenthrin, BPMC, brofenprox, bromthiofos, coxacarb, buprofezin, butanocarb, butylpyridaben,

Thiamifos, carbofuran, carbofuran, trithion, carbosulfan, cartap, CGA157419, CGA184699, chloethocarb, chlorethoxyfos, chlorpyrifos, chlorpyrifos, methyl Chlorpyrifos, cis-resmethrin, clocythrin, tetrafenazin, cypronil, promethrin, cyfluthrin-beta, cyhalothrin, tricyclotin, cypermethrin, cyromazine,

deltamethrin, demeton-M, demeton-S, demeton-methyl, difluben, diazinon, phenanophos, dichlorvos, dicliphos, dicrotophos, ethion, diflubenzuron , Dimethoate, Methamphetamine, Dioxaphos, Diphosphor,

Kewensan, emamectin, esfenvalerate, ethioncarb, ethion, etofenproxil, methionphos, pyrimathion,

Fenzafen, fenazafen, fenbutatin, fenitrothion, secbucarb, fenthiocarb, fenoxycarb, cypermethrin, fenpyrad, pyrazafen, fenthion, fenvalerate, fipronil, pyrfluroxy Difenpyr, flufenuron, flucyfenthrin, flufenuron, flufenprox, fluvalinate, tefenthion, Anguo, thiazophos, fubfenprox, furosemcarb,

HCH, Heptenphos, Hexaflumuron, Hexythiazox,

Imidacloprid, Isofrazolin, Chlorazophos, Isopropylphos, Yechansan, Oxazophos, Isofermectin, Cyhalothrin, Lufenuron,

Malathion, methomyl, methiocarb, mesulfenphos, snail enemy, chrysanthemum, methamidophos, methopon, methocarb, methomyl, methiocarb, milbemectin, monocrotophos, moxidectin,

Dibromophosphorus, NC184, NI25, nitenpyram,

Omethoate, kill line, sulfoxide absorb phosphorus, isosulfone phosphorus,

Parathion-A, parathion-M, permethrin, Daofengsan, phorate, thion, imidophos, phosphamide, phoxim, anti-budcarb, pirimiphos-methyl, Pirimiphos-A, profenofos, monsoxur, profenfos, propoxur, prothion, fagus, pymetrozin, pyrazophos, pyraphenthion, pyresmethrin, pyrethrin, pyridaben, pyrimidifen, pyriproxyfen ,

Quetiaphos,

RH5992,

Vegetable and fruit phosphorus, sebufos, silafluofen, fenitrothion, methionon,

tebufenozid, tebufenpyrad, tebupirimiphos, fururon, tefluthrin, tefluthion, terdicarb, terbufos, insecticide, thiafenox, thiodicarb, monocrotophos, methionon, nematofen , thuringiensin, perbromethrin, fenthiacarid, triazophos, triazuron, trichlorfon, triflumeron, proncarb,

Yamieduo, XMC, Mishacarb, YI5301/5302, zetamethrin.

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

The active compounds according to the invention can also be present in their commercial formulations and in the use forms prepared from these formulations as a mixture with synergists. Synergists are compounds which increase the action of the active compounds without themselves being active.

The active compound content of the use forms prepared from the commercial formulations can vary within wide ranges. The active compound concentration of the use forms is 0.0000001-95% by weight of active compound, preferably 0.0001-1% by weight.

The compounds are applied in a customary manner suitable for the use forms.

When used against sanitary field pests and stored product pests, these active compounds have excellent residual action on wood and clay and good stability to alkali on limed materials.

The active compounds of the present invention are not only active against plant, hygienic and stored product pests, but are also used in the field of veterinary medicine to kill animal parasites (ectoparasites), such as hard ticks, soft ticks, itchy mites, chiggers, flies ( bite and suck), parasitic fly larvae, lice, head lice, bird lice and fleas. Such parasites include:

From the order of Anolpurida, for example, Haematopinus spp., Linognathus spp., Pediculus spp., Phtirus spp., Solenopotes spp. .

Biting lice (Mallophagida) and Amblycerina and Ischnocerina suborders, such as Trimenopon spp., Menopon spp., Trinoton spp., Bovicola spp., Werneckiella spp., Lepikentron spp., Damalina spp., Trichodectes spp., Felcolas pp.

Diptera and Nematocerina and Brachycerina suborders, such as Aedes spp., Anopheles spp., Culex spp., Simulium gnats spp.), Eusimulium spp., Sandfly (Phlebotomus spp.), Lutzomyia spp., Culicoides spp., Chrysops spp., Tumor fly ( Hybomitra spp., Atylotus spp., Tabanus spp., Haematopotaspp., Philipomyia spp., Braula spp., Musca spp., Hydrotuea spp., Stomoxys spp.), Haematobia spp., Morellia spp., Fannia spp., Glossina spp., Calliphoraspp., Lucilia spp., Chrysomyia spp., Wohlfahrtia spp., Sarcophaga spp., Oestrus spp. , Hypoderma spp., Gasterophilus spp., Hippobosca spp., Lipoptena spp., and Melophagus spp.

From the order of Siphonapterida, for example, Pulex spp., Ctenocephalides spp., Xenopsylla spp., and Ceratophyllus spp.

From the suborder of the Heteropterida, for example, Cimex spp., Triatoma spp., Rhodnius spp., and Panstrongylus spp.

From the order of non-blattas (Blattarida), for example, Blatta orientalis, Periplaneta americana, Blattela germanica, Supella spp.

Mites subclass (Acarida), and order Metastigmata and Mesostigmata, for example, Argas spp., Ornithodorus spp. Otabius spp.), Ixodess pp., Amblyomma spp., Boophilus spp., Dermacentor spp., Haemophysalis spp., Hyalomma spp. ), Rhipicephalus spp., Dermanyssus spp., Railietia spp., Pneumonyssus spp., Sternostoma spp., and Varroa spp.

Actinedida (Chigger, Prostigmata) and Acaridida (Astigmata), such as Acarapis spp., Cheyletiella spp., Ornithocheyletia spp., Myobia spp., Sarcoptes (Psorergates spp.), Demodex ( Demodex spp.), Chiggers (Trombocula spp.), Listrophorus spp., Acarus spp., Tyrophagus spp., Caloglyphus spp., Hypodectes spp., Wings Genus (Pterolichus spp.), Chiggers (Psoroptes spp.), Chiggers (Chorioptes spp.), Octodectes spp., Scabies (Sarcoptes spp.), Notoedres spp., Foot mites (Knemidocoptes spp.,), Cytodites spp. , and Laminosioptess pp.

The active compounds of the formula (I) according to the invention are also suitable for killing arthropods which infest agricultural production livestock such as cattle, sheep, goats, horses, pigs, donkeys, camels, buffaloes, rabbits, chickens, turkeys, Ducks, geese, bees, other pets such as dogs, cats, caged birds and aquarium fish, and animals known as laboratory animals such as hamsters, guinea pigs, rats and mice. By controlling these arthropods, livestock mortality can be reduced and yields can be increased (eg meat, milk, wool, skins, eggs, honey, etc.), so that more economical and simpler animal husbandry can be achieved by using the active compounds according to the invention.

In the field of veterinary medicine, the active compounds according to the invention are used in a known manner by enteral administration, for example in the form of tablets, capsules, dips, dips, granules, pastes, boluses, by feeding methods, suppositories, By parenteral administration, e.g. by injection (intramuscular, subcutaneous, intravenous, intraperitoneal, etc.), implantation, nasal administration, by e.g. dipping or bathing, spraying, pouring and spotting, washing Dermal administration in the form of powders and powders can also be used by means of shaped articles containing the active compound, such as neck rings, earrings, tail ornaments, leg bands, bridles, markers and the like.

When used to livestock, poultry, pets, etc., the active compound of formula (I) of the present invention can be used as a preparation (such as powder, emulsion, flowable agent) containing the active compound in an amount of 1-80% by weight, directly It can be used after being diluted 100-10000 times, or it can be used in the form of chemical bath.

In addition, it has been found that the compounds of the formula (I) according to the present invention also have a strong insecticidal action against insects which damage industrial materials.

As examples, the following insects may preferably be mentioned, but without limitation:

beetles such as

Hylotrupes bajulus,Chlorophorus pilosis,Anobium punctatum,Xestobium rufovillosum,Ptilinuspectiornis,Dendrobium pertinex,Ernobius mollis,Priobiumcarpini,Lyctus brunneus,Lyctus africanus,Lyctus africanus planicollis), Lyctus linearis, Lyctuspubescens, Trogoxylon aequale, Minthes rugicollis, bark beetle (Xyleborus spec.), Tryptodendron spec., Apate monachus, Bostrychus capucins, Heterobostrychus branneus, Simoxylonspec., and bamboo beetle (Dinoderus minutus).

From the order of the Hymenoptera (Dermapterans), for example

Steel blue hornet (Sirex juvencus), fir hornet (Urocerus gigas), Urocerus gigas taignus and Urocerus augur.

termites such as

Kalotermes flavicollis, Cryptotermes brevis, Heterotermes indicola, Reticulitermes flavipes, Reticulitermessantonensis, Reticulitermes lucifugus, Australian termite (Mastotermes darwiniensis), Zootermopsis nevadensis and Taiwanese house termite (Coptotermes formosanus).

Bristle-tail, such as unicorn (Lepisma saccharina).

Industrial materials referred to in the present invention are to be understood as meaning non-living materials, for example, preferably synthetic materials, adhesives, sizes, paper and cardboard, leather, wood and woodworking products and coatings.

Very particular materials to be protected against insect infestation are wood and wood processed products.

Wood and wood-worked products which can be protected with a composition according to the invention or a mixture containing such a composition are understood to be, for example, construction woodwork, wooden beams, railroad ties, bridge-building timbers, piers, wooden vehicles, boxes , formwork, containers, utility poles, barrels, windows, doors, plywood, particle board, joints, or wood products commonly used in house building or joinery trades.

The active compounds according to the invention can be employed as such, in the form of emulsifiable concentrates or generally customary preparations such as powders, granules, solutions, suspensions, emulsions or pastes.

The formulations can be prepared in a manner known per se, for example by mixing the active compound with at least one solvent or diluent, emulsifier, dispersant and/or binder or fixative, water repellant and, if appropriate, desiccant and UV stabilizers and, if appropriate, colorants and pigments and other processing aids.

The insecticide compositions or concentrates for the protection of wood and wood products contain the active compounds according to the invention in concentrations of 0.0001 to 95% by weight, in particular 0.001 to 60% by weight.

The amount of composition or concentrate used depends on the species and occurrence of the pest and on the medium. The optimum ratios to be applied can be determined in each case by means of test series. In general, however, it is sufficient to use 0.0001-20% by weight, preferably 0.001-10% by weight, of active compound, based on the material to be protected.

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

Organic chemical solvents used with preference are oils or oily solvents having a volatility number of greater than 35 and a flash point of greater than 30°C, preferably greater than 45°C. Substances used as such oils and oily solvents having low volatility and being insoluble in water are suitable mineral oils or their aromatic fractions, or solvent mixtures containing mineral oils, preferably white spirit, petroleum and/or Alkylbenzene.

Advantageously used substances are mineral oils with a boiling point range of 170-220° C., white spirits with a boiling point range of 170-220° C., spindle oils with a boiling point range of 250-350° C., petroleum or aromatic oils with a boiling point range of 160-280° C. family compounds, turpentine essential oil, etc.

In a preferred embodiment, the substances used are liquid aliphatic hydrocarbons with a boiling point range of 180-210° C. or high boiling mixtures of aromatic and aliphatic hydrocarbons with a boiling point range of 180-220° C. and/or spindle oils and/or monochloro Naphthalene, preferably α-monochloronaphthalene.

Low-volatility organic oils or oil-based solvents with a volatility number greater than 35 and a flash point above 30°C, preferably above 45°C, can be partially replaced by high-volatility or medium-volatility organic chemical solvents, provided that the solvent mixture Also has a volatility number greater than 35 and a flash point greater than 30°C, preferably greater than 45°C, and the insecticidal/fungicidal mixture is soluble or emulsifiable in the solvent mixture.

In a preferred embodiment, part of the organic chemical solvent or solvent mixture is replaced by an aliphatic polar organic chemical solvent or solvent mixture. Substances used with preference are aliphatic organic chemical solvents having 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 adhesive drying oils known per se and can be diluted with water and/or are soluble, dispersible or dispersible in the organic chemical solvents used. Emulsified, especially adhesives consisting of or containing: acrylic resins, vinyl resins such as 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 adhesives based on natural and/or synthetic resins .

The synthetic resin used as the binder can be used in the form of emulsion, dispersion or solution. Up to 10% by weight of bitumen or bitumen-like substances can also be used as binder. In addition, colorants, pigments, water repellents, odor-masking substances and inhibitors or corrosion inhibitors etc. known per se can also be used.

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

All or part of the above-mentioned adhesive may be replaced by a fixative (mixture) or a plasticizer (mixture). These additives are intended to prevent volatilization and crystallization or precipitation of the active compound. Preferably, 0.01-30% of the binder is replaced (based on 100% binder used).

Plasticizers come from chemical grades of phthalates such as dibutyl phthalate, dioctyl phthalate or benzyl butyl phthalate, phosphate esters such as tributyl phosphate, hexyl Diacid esters such as di-(2-ethylhexyl) adipate, stearates such as butyl stearate or amyl stearate, oleates such as butyl oleate, glyceryl ether or Higher molecular weight glycol ethers, glycerides and p-toluene sulfonates.

The chemical basis of the fixatives are polyvinyl alkyl ethers, for example polyvinyl methyl ether, or ketones, such as benzophenone or ethylenebenzophenone.

Also particularly suitable as solvent or diluent is water, if appropriate in admixture with one or more of the abovementioned organic chemical solvents or diluents, emulsifiers and dispersants.

Particularly effective wood protection is achieved by numerous industrial impregnation methods, such as vacuum, double vacuum or pressurized methods.

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

Suitable additional ingredients which may be admixed are preferably the insecticides and fungicides mentioned in WO94/29268. The compounds mentioned in this document are expressly incorporated into the present application by reference.

Very particularly preferred ingredients which may be mixed are insecticides such as chlorpyrifos, phoxim, silafluofin, alpha-cypermethrin, cyfluthrin, cypermethrin, deltamethrin, permethrin, imidacloprid, NI-25, sulfiflunium Urea, hexaflumuron, and trimezuron, and fungicides such as epoxyconazole, hexaconazole, teconazole, cyproconazole, tebuconazole, cyproconazole, metconazole, imazalil, benflusulfonamide, tolueneflu Sulfonamide, 3-iodo-2-propynylbutyl carbamate, N-octyl-isothiazolin-3-one and 4,5-dichloro-N-octylisothiazolin-3-one.

The preparation and use of the active compounds according to the invention are illustrated by the following examples. Preparation Example Example 1 (method a)

Add dropwise 3.50 g (0.012 mol) [4-(4-nitrobenzene Oxy)]-phenylacetyl chloride solution. The mixture was stirred at 25°C for 18 hours, then concentrated to dryness. The reaction mixture was dissolved in water/ethyl acetate, and the organic phase was washed repeatedly with 10% aqueous sodium hydroxide. After drying and concentration, a viscous residue was obtained which was purified by silica gel chromatography using dichloromethane/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)]-phenylacetamide of melting point 223° C.

^*)m.p.(℃)or¹HNMR,δppm,d⁶-DMSO)应用实施例实施例A猿叶虫(Phaedon)幼虫试验溶剂：7份重量二甲基甲酰胺乳化剂：1份重量烷基芳基聚乙二醇醚Analogously, and/or following the general preparation instructions, the following compounds of formula (I) are obtained:

^* )mp (°C) or ¹ HNMR, δppm, d ⁶ -DMSO) Application Examples Example A Test on Phaedon larvae Solvent: 7 parts by weight Dimethylformamide Emulsifier: 1 part by weight Alkyl aromatic polyglycol ether

To prepare a suitable preparation of the active compound, 1 part by weight of the active compound is mixed with the stated amount of solvent and the stated amount of emulsifier, and the emulsifiable concentrate is diluted with water to the required concentration.

Cabbage leaves ( Brassica oleracea ) are treated by being dipped into the preparation of active compound of the desired concentration and infested with larvae of the horseradish beetle ( Phaedon cochleariae ) while the leaves are still moist.

After a certain period of time, the percent kill is determined. 100% means that all beetle larvae have been killed; 0% means that none of the beetle larvae have been killed.

In this test, at the exemplary active compound concentration of 0.1%, for example the compound of Preparation Example 2 achieves 100% kill after 7 days. Embodiment B lawn armyworm (Spodoptera Frugiperda) test solvent: 7 parts by weight dimethylformamide emulsifier: 1 part by weight alkyl aryl polyglycol ether

To prepare a suitable preparation of the active compound, 1 part by weight of the active compound is mixed with the stated amount of solvent and the stated amount of emulsifier, and the emulsifiable concentrate is diluted with water to the required concentration.

Cabbage leaves ( Brassica oleracea ) are treated by being dipped into the preparation of active compound of the desired concentration and are infested with caterpillars of the grass armyworm ( Spodoptera frugiperda ) while the leaves are still moist.

After a certain period of time, the percent kill is determined. 100% means that all caterpillars have been killed; 0% means that none of the caterpillars have been killed.

In this test, at the exemplary active compound concentration of 0.1%, for example the compound of Preparation Example 2 achieves a 100% kill after 7 days. Example C leafhopper (Nephotettix) test solvent: 7 parts by weight dimethylformamide emulsifier: 1 part by weight alkyl aryl polyglycol ether

To prepare a suitable preparation of the active compound, 1 part by weight of the active compound is mixed with the stated amount of solvent and the stated amount of emulsifier, and the emulsifiable concentrate is diluted with water to the required concentration.

Rice seedlings ( Oryza esativa ) are treated by being dipped into the preparation of active compound of the desired concentration and are infested with larvae of the black-tailed leafhopper ( Nephotettix cincticeps ) while the seedlings are still moist.

After a certain period of time, the percent kill is determined. 100% means that all leafhoppers have been killed; 0% means that none of the leafhoppers have been killed.

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

Claims (10)

1. Compound of formula (I)

where Q represents the group

Wherein Het represents an optionally substituted heterocyclic ring, R represents hydrogen, alkyl, haloalkyl, alkoxyalkyl, alkylcarbonyl, alkylsulfonyl, represents each optionally substituted arylcarbonyl, arylsulfonyl Acyl or arylalkyl, or represent optionally substituted cycloalkyl, X represents oxygen or sulfur, Y represents optionally substituted alkylene, alkenylene, alkyleneoxy or alkylenethio and A represents optionally substituted aryl, optionally substituted cycloalkyl, optionally substituted cycloalkenyl or optionally substituted heterocycle. 2. The formula (I) compound of claim 1, wherein Q represents the group

Wherein Het represents a 5- or 6-membered heterocyclic ring having 1 or 2 heteroatoms such as N, S and O atoms, optionally substituted one to three times by the same or different substituents, the possible substituents being halogen, C ₁ - C ₄ -alkyl, C ₁ -C ₄ -alkoxy, C ₁ -C 4 -haloalkyl having 1 to 5 identical or different halogen atoms such as fluorine, chlorine and bromine atoms, C ₁ -C _{4 -} Alkoxy-C ₁ -C ₄ -alkyl, nitro, C ₁ -C ₄ -alkylsulfonyl, C ₁ -C ₄ -with 1 to 5 identical or different halogen atoms such as fluorine and chlorine atoms Haloalkylsulfonyl, also thiocarbamoyl, R represents hydrogen, C ₁ -C ₄ -alkyl, C ₁ -C ₄ -halogenated alkyl having 1 to 5 identical or different halogen atoms, such as fluorine and chlorine atoms radical, C ₁ -C ₄ -alkoxy-C ₁ -C ₄ -alkyl, C ₁ -C ₄ -alkylcarbonyl, C ₁ -C ₄ -alkylsulfonyl, stands for phenylcarbonyl, phenylsulfonyl Acyl or benzyl, each optionally one to three substituted on the phenyl ring by identical or different substituents, possible substituents being in each case halogen, nitro, cyano, C ₁ -C ₄ -alk _{C 1} -C ₂ -haloalkyl _, C 1 -C 4 -alkoxy, C ₁ -C ₄ -alkylthio with 1 to 5 identical or different halogen atoms such as fluorine and chlorine atoms, with 1 - C ₁ -C ₂ -haloalkoxy with 5 identical or different halogen atoms such as fluorine and chlorine atoms, C ₁ -C ₂ -halogenated alkylthio with 1 to 5 identical or different halogen atoms such as fluorine and chlorine atoms or represents a C ₃ -C ₆ -cycloalkyl optionally substituted by the same or different substituents selected from C ₁ -C ₄ -alkyl and halogen, X represents oxygen or sulfur, Y represents 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, C ₁ -C ₄ -halogenated alkylene having 1 to 5 identical or different halogen atoms such as fluorine and chlorine atoms Alkyl; _{C 3} -C ₆ -cycloalkyl-C 1 -C 4 -alkylene, C ₂ -C ₄ , optionally mono- to trisubstituted by identical or different substituents selected from fluorine _, chlorine and methyl -alkenylene, C ₁ -C ₄ -alkyleneoxy or C ₁ -C ₄ -alkylenethio, A(1) represents phenyl optionally substituted one to three times by identical or different substituents , possible substituents are: halogen, nitro, cyano, C ₁ -C ₁₂ -alkyl, C ₁ -C ₁₂ -haloalkyl with 1 to 5 identical or different halogen atoms such as fluorine and chlorine atoms, C ₁ -C ₁₂ -alkoxy, C ₁ -C ₁₂ -halogenated alkoxy, C ₁ -C ₁₂ -alkylthio, having 1-5 identical or different halogen atoms such as fluorine and chlorine atoms, having 1- C ₁ -C ₁₂ -haloalkylthio, C ₂ -C ₁₂ -alkenyl having 5 identical or different halogen atoms, such as fluorine and chlorine atoms, having 1 to 5 identical or different halogen atoms, such as fluorine and chlorine atoms C ₁ -C ₁₂ -haloalkenyl, C ₃ -C ₈ -cycloalkyl optionally mono- to trisubstituted by identical or different substituents selected from C ₁ -C ₄ -alkyl and halogen, below the group Also phenyl, phenoxy, thiophenyl, benzyl, benzyloxy, pyridyloxy, pyrimidinyloxy, pyrazinyloxy or pyridazinyloxy, each of which is optionally The same or different groups selected from one to three substitutions: halogen, nitro, cyano, thiocarbamoyl, C ₁ -C ₄ -alkyl, with 1 to 5 identical or different halogen atoms such as fluorine C ₁ -C ₄ -haloalkyl, C ₁ -C ₄ -alkoxy, C ₁ -C ₄ -alkoxy-C ₁ -C ₄ -alkyl, with 1 to 5 identical or different C ₁ -C ₄ -haloalkoxy of halogen atoms such as fluorine and chlorine atoms, C ₁ -C ₄ -alkylthio, C ₁ -C having 1 to 5 identical or different halogen atoms such as fluorine and chlorine atoms ₄ -Haloalkylthio, 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, with 1 to 5 identical or different halogen atoms For example C ₁ -C ₄ -haloalkylsulfonyl, formyl, C ₁ -C ₄ -alkylcarbonyl, C ₁ -C ₄ -alkoxycarbonyl, C ₁ -C ₄ -alkoxy for fluorine and chlorine atoms Imino-C ₁ -C ₄ -alkyl, optionally C ₁ -C ₄ -alkyl-substituted oxadiazolyl or one of the following groups (2) stands for C ₅ -C ₈ -cycloalkenyl or C ₃ -C ₈ -cycloalkyl optionally substituted by one to five identical or different substituents, possible substituents being C ₁ -C ₄ -alkyl , C ₁ -C ₄ -haloalkyl having 1 to 5 identical or different halogen atoms such as fluorine and chlorine atoms, C ₁ -C ₄ -alkoxy having 1 to 5 identical or different halogen atoms such as fluorine C ₁ -C ₄ -haloalkoxy, C ₃ -C ₈ -cycloalkyl, and optionally identical or different ones selected from halogen, nitro, cyano, C ₁ -C ₄ -alkyl , C ₁ -C ₄ -haloalkyl having 1 to 5 identical or different halogen atoms such as fluorine and chlorine atoms, C ₁ -C ₄ -alkoxy and having 1 to 5 identical or different halogen atoms such as fluorine and chlorine atom C ₁ -C ₄ -halogenated alkoxy substituents mono- to tri-substituted phenyl; (3) Represents 1-3 heteroatoms such as N, S and O atoms, may optionally also contain one or more CO and/or CS groups as ring members, and are optionally substituted by the same or different - to trisubstituted 5- or 6-membered heterocyclic rings, possible substituents are: halogen, nitro, cyano, C ₁ -C ₄ -alkyl, C ₁ -C ₄ -alkoxy, C ₁ -C ₄ -Alkylthio, C ₁ -C ₄ -haloalkyl having 1 to 5 identical or different halogen atoms such as fluorine and chlorine atoms, having 1 to 5 identical or different halogen atoms such as fluorine and chlorine atoms C ₁ -C ₄ -halogenated alkoxy, C ₁ -C ₄ -halogenated alkylthio having 1 to 5 identical or different halogen atoms such as fluorine and chlorine atoms, or representing each optionally substituted by the same or different substituents Mono- to trisubstituted phenyl, phenoxy, thiophenyl or benzyl, possible substituents are: halogen, nitro, cyano, C ₁ -C ₄ -alkyl, C ₁ -C ₄ -alkoxy , C ₁ -C ₄ -alkylthio, C ₁ -C ₄ -haloalkyl having 1 to 5 identical or different halogen atoms such as fluorine and chlorine atoms, having 1 to 5 identical or different halogen atoms such as fluorine C ₁ -C ₄ -halogenated alkoxy with chlorine atoms, C ₁ -C ₄ -halogenated alkylthio with 1 to 5 identical or different halogen atoms such as fluorine and chlorine atoms; and wherein hydrogen atoms can optionally be substituted NH groups present in heterocycles may be substituted by C ₁ -C ₆ -alkyl, C ₁ -C ₆ -alkylcarbonyl or phenylsulfonyl, and these substituents may in turn be optionally replaced by C ₁ -C ₆ -Alkyl, halogen, C 1 -C 4 -haloalkyl with 1 to 5 identical or different _halogen atoms _{, for example fluorine and chlorine atoms, C 1 -C 4} -alkoxy or with 1 to 5 identical or C ₁ -C ₄ -haloalkoxy substitution of different halogen atoms such as fluorine and chlorine atoms; (4) represents a fused compound containing one or more heteroatoms such as N, S or O atoms, or one or more CO groups as ring members, and optionally substituted by the same or different substituents from one to five Bi- or tricyclic groups, possible substituents are: halogen, nitro, cyano, C ₁ -C ₄ -alkyl, C ₁ with 1 to 5 identical or different halogen atoms such as fluorine and chlorine atoms -C ₄ -haloalkyl, C ₁ -C ₄ -alkoxy-C ₁ -C ₄ -alkyl, C ₁ -C ₄ -alkoxy, with 1 to 5 identical or different halogen atoms such as fluorine and C ₁ -C ₄ -haloalkoxy of chlorine atoms, C ₁ -C ₄ -alkylthio, C ₁ -C ₄ -haloalkylthio having 1 to 5 identical or different halogen atoms, for example fluorine and chlorine atoms, C ₁ -C ₄ -alkylsulfinyl, C ₁ -C ₄ -alkylsulfonyl, hydroxy, mercapto, C ₁ -C ₄ -alkylcarbonyl, with 1 to 5 identical or different halogen atoms such as fluorine C ₁ -C ₄ -haloalkylcarbonyl with chlorine atom, C ₁ -C ₄ -alkoxycarbonyl or each optionally substituted one to three times by identical or different substituents, especially phenyl substituted in the phenyl moiety, Phenoxy, phenylthio or benzyl, possible substituents are: halogen, nitro, cyano, C ₁ -C ₄ -alkyl, C ₁ -C ₄ -alkoxy, C ₁ -C ₄ - Alkylthio, C ₁ -C ₄ -haloalkyl having 1 to 5 identical or different halogen atoms such as fluorine and chlorine atoms, C ₁ - having 1 to 5 identical or different halogen atoms such as fluorine and chlorine atoms C ₄ -haloalkoxy, C ₁ -C ₄ -haloalkylthio having 1 to 5 identical or different halogen atoms, such as fluorine and chlorine atoms; wherein R ¹ represents hydrogen, C ₁ -C ₈ -alkyl, having C ₁ -C ₄ -haloalkyl groups of 1 to 5 identical or different halogen atoms such as fluorine and chlorine atoms, representing optionally identical or different substituents selected from halogen and C ₁ -C ₄ -alkyl groups - or Polysubstituted C ₃ -C ₇ -cycloalkyl, or stands for phenyl optionally one to three substituted by identical or different substituents, possible substituents are halogen, C ₁ -C ₄ -alkyl or C ₁ - C ₄ -alkoxy, R ² and R ³ are the same or different, each representing hydrogen or C ₁ -C ₄ -alkyl; R ⁴ represents C ₁ -C ₈ -alkyl, having 1 to 5 identical or C ₁ -C _{4 -haloalkyl} groups of different halogen atoms such as fluorine and chlorine atoms represent _{C 3} - C ₇ -cycloalkyl, or stands for phenyl optionally one to three substituted by identical or different substituents, possible substituents are halogen, C ₁ -C ₄ -alkyl or C ₁ -C ₄ -alkoxy and W represents one of oxygen or groups =N-OR ⁵ and =N-NR ⁶ R ⁷ , wherein R ⁵ represents C ₁ -C ₆ -alkyl or represents optionally the same or different selected from halogen, nitr radical, cyano, thiocarbamoyl, C ₁ -C ₄ -alkyl, C ₁ -C ₄ -haloalkyl having 1 to 5 identical or different halogen atoms such as fluorine and chlorine atoms, C ₁ -C ₄ -Alkoxy, C ₁ -C ₄ -alkoxy- _C 1 -C 4 -alkyl, C ₁ -C ₄ -haloalkoxy with 1 _to 5 identical or different halogen atoms such as fluorine and chlorine atoms C ₁ -C ₄ -alkylthio, _{C 1} -C 4 -haloalkylthio having 1 to 5 identical or different halogen atoms such as fluorine and chlorine atoms, 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, C 1 -C 4 -Haloalkylsulfonyl} having 1 to 5 identical or different halogen atoms such as fluorine and chlorine atoms, Formyl, C ₁ -C ₄ -alkylcarbonyl, C ₁ -C ₄ -alkoxycarbonyl and C ₁ -C ₄ -alkoxyimino-C ₁ -C ₄ -alkyl substituents one to three Substituted benzyl; and R ⁶ and R ⁷ are the same or different, each represents hydrogen, C ₁ -C ₆ -alkyl or represents phenyl optionally substituted one to three times by identical or different substituents, possible substitutions The radical is halogen, nitro, cyano, C ₁ -C _{4 -alkyl, C 1 -C 4} -haloalkyl having 1 to 5 identical or _different halogen atoms such as fluorine and chlorine atoms, C _{1 -C 4} -alkoxy or C ₁ -C ₄ -haloalkoxy having 1 to 5 identical or different halogen atoms, such as fluorine and chlorine atoms. 3. The formula (I) compound of claim 1, wherein Q represents one of the following groups

wherein Z ¹ , Z ² and Z ³ are the same or different, each representing hydrogen, chlorine, bromine, nitro, methyl, ethyl, n- or iso-propyl, n-, iso-, sec- or tert -Butyl; CH ₂ F, CHF ₂ , CF ₃ , CH ₂ Cl, CH ₂ Br, CHClCH ₃ ; Methoxy, ethoxy, methoxymethyl or ethoxymethyl, R represents hydrogen, form Base, ethyl, n- or i-propyl; methoxymethyl, ethoxymethyl, n-propoxymethyl, n-butoxymethyl; methylcarbonyl, methylsulfonyl; phenylcarbonyl or benzyl, each optionally mono- or disubstituted by the same or different substituents selected from fluorine, chlorine, methyl or trifluoromethyl; or represent cyclopropyl, 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- or -CH ₂ O-, A(1) represents phenyl optionally substituted by the same or different substituents one to three times, possible substituents are: halogen, nitro, cyano, C ₁ -C ₁₂ -alkyl, C ₁ -C ₁₂ -haloalkyl having 1 to 5 identical or different halogen atoms such as fluorine and chlorine atoms, C ₁ -C ₄ -alkoxy having 1 to 5 identical or C ₁ -C ₄ -haloalkoxy with different halogen atoms such as fluorine and chlorine atoms, C ₁ -C ₄ -alkylthio, C ₁ -with 1 to 5 identical or different halogen atoms such as fluorine and chlorine atoms C ₄ -haloalkylthio, C ₂ -C ₄ -alkenyl, C ₂ -C ₄ -halogenated alkenyl having 1 to 5 identical or different halogen atoms, such as fluorine and chlorine atoms, the following groups There are also phenoxy, phenylthio, benzyloxy or pyridyloxy groups, each of which is optionally substituted one to three times by the same or different substituents selected from the group consisting of halogen, nitro, cyano, sulfur Carbamoyl, C ₁ -C ₄ -alkyl, C ₁ -C ₄ -haloalkyl with 1 to 5 identical or different halogen atoms such as fluorine and chlorine atoms, C ₁ -C ₄ -alkoxy, C ₁ -C ₄ -alkoxy-C ₁ -C ₄ -alkyl, C ₁ -C ₄ -haloalkoxy with 1 to 5 identical or different halogen atoms, for example fluorine and chlorine atoms, C ₁ -C ₄ -Alkylthio, C 1 -C 4 -haloalkylthio _, C ₁ -C ₄ -alkylthio-C _{1 -C 4} -alk, having 1 to 5 identical or different halogen atoms such as fluorine and chlorine atoms radical, C ₁ -C ₄ -alkylsulfinyl-C ₁ -C ₄ -alkyl, C ₁ -C ₄ -alkylsulfonyl-C ₁ -C ₄ -alkyl, C ₁ -C ₄ -alk Sulfinyl, C ₁ -C ₄ -alkylsulfonyl, C ₁ -C ₄ -haloalkylsulfonyl having 1 to 5 identical or different halogen atoms such as fluorine and chlorine atoms, formyl, C ₁ - C ₄ -Alkylcarbonyl, C ₁ -C ₄ -Alkoxycarbonyl, C ₁ -C ₄ -Alkoxyimino-C ₁ -C ₂ -Alkyl, optionally C ₁ -C ₂ -Alkyl Group-substituted oxadiazol-3-yl and one of the following groups

(2) represents cyclopentyl, cyclohexyl, cyclopentenyl or cyclohexenyl optionally substituted by one to five identical or different substituents, possible substituents are fluorine, chlorine, bromine, methyl, ethyl , isopropyl, methoxy or trifluoromethyl, (3) represents the following heterocycles optionally substituted one or two by the same or different substituents:

Suitable substituents in each case are: fluorine, chlorine, nitro, cyano; methyl, ethyl, n- or i-propyl, n-, i-, sec- or tert-butyl; methoxy Base, ethoxy, n- or i-propoxy; methylthio; -CF ₃ , -CHF ₂ , -CH ₂ CF ₃ , -CH ₂ -CF ₂ -CHF ₂ , -CH(CF ₃ )- CH ₃ ; -OCF ₃ , -OCHF ₂ , OCH ₂ CF ₃ , -O-CH ₂ -CF ₂ -CF ₃ , -OCH ₂ -CF ₂ -CHF ₂ , -O-CH(CF ₃ )-CH ₃ ; -SCF ₃ ; and phenyl, phenoxy or thiophenyl, each optionally mono- or disubstituted by the same or different substituents, possible substituents are: fluorine, chlorine, nitro, cyano, methyl, Ethyl, methoxy, ethoxy ^, methylthio, trifluoromethyl, trifluoromethoxy or trifluoromethylthio; wherein R represents C ₁ -C ₄ -alkyl, especially methyl or Ethyl; C ₁ -C ₄ -Alkylcarbonyl, especially methylcarbonyl or ethylcarbonyl; and representatives optionally identically or differently selected from C ₁ -C ₄ -Alkyl, especially methyl or ethyl ; halogen, especially fluorine or chlorine; C ₁ -C ₄ -haloalkyl, especially trifluoromethyl; C ₁ -C ₄ -alkoxy, especially methoxy; and C ₁ -C ₄ -haloalkoxy radical, especially trifluoromethoxy substituent mono- or disubstituted phenylsulfonyl; or (4) represents the following bi- or tricyclic groups that are connected as required and optionally substituted by one to four identical or different substituents:

Adamantyl

Possible substituents in each case are: fluorine, chlorine, bromine, nitro, cyano; methyl, ethyl; methoxy, methylthio, trifluoromethyl, trifluoromethoxy or trifluoromethyl Sulfuryl; Wherein R ¹ represents hydrogen, methyl, ethyl, n- or iso-propyl, n-, iso-, sec- or tert-butyl, represents optionally selected from the same or different fluorine, chlorine, C ₃ -C ₇ -cycloalkyl substituted one to five times by the substituents of bromine and methyl, or represents phenyl optionally substituted one to three times by identical or different substituents, possible substituents are fluorine, chlorine, bromine, Methyl, ethyl, n- or i-propyl, methoxy or ethoxy, ^R2 and ^R3 are the same or different, each representing hydrogen, methyl, ethyl, n- or i-propyl , n-, iso-, sec- or tert-butyl; R ⁴ represents methyl, ethyl, n- or i-propyl, n-, iso-, sec- or tert-butyl, represents optionally identical or C ₃ -C ₇ -cycloalkyl groups which are one to five substituted (preferably one to three substituted) with different substituents selected from fluorine, chlorine, bromine and methyl, or represent optionally one to three substituted with the same or different substituents phenyl, possible substituents are fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, methoxy or ethoxy; and W represents oxygen or the group =N-OR ⁵ and = one of N-NR ⁶ R ⁷ , wherein R ⁵ represents C ₁ -C ₄ -alkyl or represents benzyl optionally substituted one to three times by the same or different substituents, possible substituents are fluorine, chlorine, bromine , nitro, cyano, trifluoromethyl, trifluoromethoxy, methylthio, methylsulfinyl, methylsulfonyl, methyl, ethyl, n- or i-propyl, n-, Iso-, sec- or tert-butyl, methoxy or ethoxy; and R ⁶ and R ⁷ are the same or different, each represents hydrogen, C ₁ -C ₄ -alkyl or represents optionally identical or different Substituents for mono- to tri-substituted phenyl, possible substituents are fluorine, chlorine, bromine, nitro, cyano, methyl, ethyl, trifluoromethyl, methoxy or trifluoromethoxy. 4. The formula (I) compound of claim 1, wherein Q represents one of the following groups wherein ^Z1 and ^Z2 are the same or different, each represents hydrogen, chlorine, bromine, nitro, methyl, ethyl, methoxy or ethoxy, and R represents hydrogen, methyl, ethyl, methoxy Methyl, ethoxymethyl, methylcarbonyl, phenylcarbonyl or methylsulfonyl, X represents oxygen or sulfur, Y represents -CH ₂ -, A represents optionally one to three substituted by the same or different substituents Phenyl, possible substituents are: fluorine, chlorine, bromine, nitro, cyano, methyl, ethyl, n- or i-propyl, n-, i-, sec- or tert-butyl, methoxy ethoxy, n- or i-propoxy, n-, i-, sec- or tert-butoxy; methylthio, CF ₃ , OCF ₃ , OCHF ₂ , SCF ₃ , SCCl ₂ F; CH ₂ Br, CH ₂ Cl; group Also phenoxy optionally substituted one to three times by the same or different substituents selected from the group consisting of fluorine, chlorine, bromine, nitro, cyano, thiocarbamoyl, methyl, ethyl, n-or iso-propyl, n-, iso-, sec- or tert-butyl, methoxy, ethoxy, n- or i-propoxy, n-, iso-, sec- or tert-butoxy; Thio, methylthiomethyl, CF ₃ , OCF ₃ , OCHF ₂ , SCF ₃ , SCCl ₂ F; CH ₂ Br, CH ₂ Cl, methoxycarbonyl, methylsulfinyl, methylsulfonyl, trifluoro Methylsulfonyl or group

wherein R ¹ represents hydrogen, methyl or ethyl; R ² and R ³ are the same or different, each representing hydrogen or methyl; R ⁴ represents methyl or ethyl; and W represents oxygen or the group =N-OR ⁵ , wherein R ⁵ represents methyl, ethyl, n- or i-propyl, n-, i-, sec- or tert-butyl, or represents benzyl optionally substituted one to three times by the same or different substituents , possible substituents are selected from fluorine, chlorine, bromine, nitro, cyano, methyl, ethyl, methoxy or ethoxy. 5. Process for the preparation of compounds of formula (I) according to claim 1, characterized in that a) In the presence of a base and in the presence of a diluent, the aminoisothiazole of the formula (II) is reacted with the acid halide of the formula (III) to obtain a new substituted N-isothiazolylamide of the formula (Ia)

wherein Q, R, Y and A are each as defined above,

wherein Q and R are each as defined above, Hal-CO-Y-A (III) wherein Y and A are each as defined above, and Hal represents halogen; or b) reacting the N-isothiazolylamides of formula (Ia) obtained by process (a) with a sulfurizing agent, if appropriate in the presence of a diluent, to give new substituted N-isothiazolylthioamides of formula (Ib) wherein Q, R, Y and A are each as defined above,

wherein Q, R, Y and A are each as defined above; or c) Reaction of aminoisothiazoles of formula (II) with dithioesters of formula (IV), if appropriate in the presence of a diluent, to give new substituted N-isothiazolylthioamides of formula (Ib)

wherein Q, R, Y and A are each as defined above,

wherein Q and R are each as defined above, wherein Y and A are each as defined above, and Alk represents an alkyl group or the group MO-CO- _CH2- , wherein M represents an alkali metal (eg sodium or potassium). 6. Insecticides, characterized in that they contain at least one compound of the formula (I) according to claim 1 . 7. Use of the compound of formula (I) according to claim 1 for controlling pests. 8. A method for controlling pests, characterized in that a compound of the formula (I) according to claim 1 is applied to the pests and/or their habitat. 9. Process for the preparation of insecticides, characterized in that compounds of the formula (I) according to claim 1 are mixed with extenders and/or surfactants. 10. Use of the compound of formula (I) according to claim 1 for the preparation of insecticides.