DE19630814A1 - Substituted 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

The present invention relates to new N-isothiazolyl (thio) amides, several Process for their preparation and their use in combating animal pests.

It is already known that certain N-isothiazolylamide derivatives are insecticidal Have properties (see, for example, EP-A 0 623 282 and WO-A 95/31448).

The level and / or duration of action of these previously known compounds is however, especially against certain organisms or for low users not entirely satisfactory in all areas of application.

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

in which
Q for grouping

stands,
in which
Het represents an optionally substituted heterocycle,
R represents hydrogen, alkyl, haloalkyl, alkoxyalkyl, alkylcarbonyl, alkyl sulfonyl, in each case optionally substituted arylcarbonyl, arylsulfonyl or arylalkyl or optionally substituted cycloalkyl,
X represents oxygen or sulfur,
Y represents optionally substituted alkylene, alkenylene, alkyleneoxy or alkylene thio and
A represents optionally substituted aryl, optionally substituted cycloalkyl, optionally substituted cycloalkenyl or an optionally substituted heterocycle.

It was also found that one

• a) the new substituted N-isothiazolyl amides of the formula (Ia) in which
  Q, R, Y and A have the meaning given above,
  obtained when aminoisothiazoles of the formula (II) in which
  Q and R have the meaning given above,
  with acid halides of the formula (III) Hal-CO-YA (III) in which
  Y and A have the meaning given above and
  Hal stands for halogen,
  in the presence of a base and in the presence of a diluent;
  and
• b) the new substituted N-isothiazolyl-thioamides of the formula (Ib) in which
  Q, R, Y and A have the meaning given above,
  obtained when the N-isothiazolyl amides of the formula (Ia) obtainable according to process (a) in which
  Q, R, Y and A have the meaning given above,
  with a sulfurizing agent, optionally in the presence of a diluent;
  and
• c) the new substituted N-isothiazolyl-thioamides of the formula (Ib) in which
  Q, R, Y and A have the meaning given above,
  also obtained if aminoisothiazoles of the formula (II) in which
  Q and R have the meaning given above,
  with dithioesters of the formula (IV) in which
  Y and A have the meaning given above and
  Alk stands for alkyl or the group MO-CO-CH₂-, where M stands for an alkali metal (such as sodium or potassium),
  if appropriate in the presence of a diluent.

Furthermore, it was found that the new substituted N-isothiazolyl- (thio) amides of formula (I) very well for controlling animal pests, in particular of insects, arachnids and nematodes, which are used in agriculture, in forests, occur in supply and material protection as well as in the hygiene sector are not.

Preferred substituents or ranges of the radicals listed in the formulas mentioned above and below are explained below.
Q preferably stands for the grouping

in which
Het represents an optionally mono- to trisubstituted, identically or ver differently substituted 5- or 6-membered heterocycle having 1 or 2 heteroatoms, such as N, S and O atoms, the substituents being sub
Halogen, C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkyl with 1 to 5 identical or different halogen atoms, such as fluorine, chlorine and bromine atoms, C₁-C₄-alkoxy-C₁-C₄-alkyl, nitro , C₁-C₄-alkyl sulfonyl, C₁-C₄-haloalkylsulfonyl with 1 to 5 identical or different halogen atoms, such as fluorine and chlorine atoms and thiocarbamoyl come into question.

R preferably represents hydrogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl with 1 to 5 identical or different halogen atoms, such as fluorine and Chlorine atoms, C₁-C₄-alkoxy-C₁-C₄-alkyl, C₁-C₄-alkyl-carbonyl, C₁-C₄-alkylsulfonyl, each optionally from one to three times, Phenylcar substituted identically or differently in the phenyl ring bonyl, phenylsulfonyl or benzyl, with phenyl substituents each halogen, nitro, cyano, C₁-C₄-alkyl, C₁-C₂-haloalkyl with 1 to 5 identical or different halogen atoms, such as fluorine and Chlorine atoms, C₁-C₄-alkoxy, C₁-C Alkyl-alkylthio, C₁-C₂-halogen alkoxy with 1 to 5 identical or different halogen atoms, such as Fluorine and chlorine atoms or C₁-C₂-haloalkylthio with 1 to 5 same or different halogen atoms, such as fluorine and chlorine atoms come into question, or for up to three if necessary fold, same or different by C₁-C₄ alkyl or halogen sub substituted C₃-C₆ cycloalkyl.

X preferably represents oxygen or sulfur.  

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

A is preferred

• (1) for phenyl which may be monosubstituted to trisubstituted identically or differently, the following being suitable as substituents:
  Halogen, nitro, cyano, C₁-C₁₂-alkyl, C₁-C₁₂-haloalkyl with 1 to 5 identical or different halogen atoms, such as fluorine and chlorine atoms, C₁-C₁₂-alkoxy, C₁-C₁₂-haloalkoxy with 1 to 5 identical or different Halogen atoms, such as fluorine and chlorine atoms, C₁-C₁₂-alkylthio, C₁-C₁₂-haloalkylthio with 1 to 5 identical or different halogen atoms, such as fluorine and chlorine atoms, C₁-C₁₂-alkenyl, C₁-C₁₂-haloalkenyl with 1 to 5 identical or different halogen atoms, such as fluorine and chlorine atoms, optionally single to triple, identical or different by C₁-C₄-alkyl or halogen-substituted C₃-C₈-cycloalkyl, the groupings such as
  each optionally single to triple, identical or different by halogen, nitro, cyano, thiocarbamoyl, C₁-C₄-alkyl, C₁-C₄-haloalkyl having 1 to 5 identical or different halogen atoms, such as fluorine and chlorine atoms, C₁-C₄-alkoxy , C₁-C₄-alkoxy-C₁-C₄-alkyl, C₁-C₄-haloalkoxy with 1 to 5 identical or different halogen atoms, such as fluorine and chlorine atoms, C₁-C₄-alkylthio, C₁-C₄-haloalkylthio with 1 to 5 identical or different halogen atoms, such as fluorine and chlorine atoms, C₁-C₄-alkylthio-C₁-C₄-alkyl, C₁-C₄-alkylsulfinyl-C₁-C₄-alkyl, C₁-C₄-alkylsulfonyl-C₁-C₄-alkyl, C₁-C₄ -Alkylsulfinyl, C₁-C₄-alkylsulfonyl, C₁-C₄-haloalkylsulfonyl with 1 to 5 identical or different halogen atoms, such as fluorine and chlorine atoms, formyl, C₁-C₄-alkylcarbonyl, C₁-C₄-alkoxy-carbonyl, C₁-C₄ -Alkoximino- C₁-C₄-alkyl, optionally substituted by C₁-C₄-alkyl oxa diazolyl or one of the groupings n substituted phenyl, phenyoxy, phenylthio, benzyl, benzyloxy, pyridyloxy, pyrimidyloxy, pyrazinyloxy or pyridazinyloxy;
• (2) for optionally up to five times, the same or different substituted C₃-C₈-cycloalkyl or C₅-C₈-cycloalkenyl, where as Substituents C₁-C₄-alkyl, C₁-C₄-haloalkyl with 1 to 5 of the same or various halogen atoms, such as fluorine and chlorine atoms, C₁-C₄ alkoxy, C₁-C₄ haloalkoxy with 1 to 5 identical or ver different halogen atoms, such as fluorine and chlorine atoms, C₃-C₈-cycloalkyl, as well as, if necessary, up to three times the same or differentiated by halogen, cyano, nitro, C₁-C₄-alkyl, C₁-C₄-haloalkyl with 1 to 5 identical or different halogen atoms, such as fluorine and chlorine atoms, C₁-C₄-alkoxy, or C₁-C₄-haloalkoxy with 1 to 5 identical or different halo gene atoms, such as fluorine and chlorine atoms, substituted phenyl in Question come;
• (3) for an optionally mono- to trisubstituted, identically or ver differently substituted 5- or 6-membered heterocycle having 1 to 3 heteroatoms, such as N, S and O atoms, which optionally also has one or more CO groups as ring members may contain, the following being suitable as substituents:
  Halogen, nitro, cyano, C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₄-alkyl thio, C₁-C₄-haloalkyl with 1 to 5 identical or different halogen atoms, such as fluorine and chlorine atoms, C₁-C₄-haloalkoxy with 1 to 5 identical or different halogen atoms, such as fluorine and chlorine atoms, C₁-C₄-haloalkylthio with 1 to 5 identical or different halogen atoms, such as fluorine and chlorine atoms or in each case optionally up to three times, identical or differently substituted phenyl, phenoxy, Phenylthio or benzyl, where the following are suitable as substituents:
  Halogen, nitro, cyano, C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₄-alkyl thio, C₁-C₄-haloalkyl with 1 to 5 identical or different halogen atoms, such as fluorine and chlorine atoms, C₁-C₄-haloalkoxy with 1 to 5 identical or different halogen atoms, such as fluorine and chlorine atoms and C₁-C₄-haloalkylthio with 1 to 5 identical or different halogen atoms, such as fluorine and chlorine atoms; and where an NH group which may be present in the heterocycle may be substituted for C₁-C₆-alkyl, C₁-C₆-alkylcarbonyl or phenylsulfonyl instead of the hydrogen atom, which in turn may optionally be substituted by C₁-C₆-alkyl, halogen, C₁-C₄-haloalkyl, C₁-C₄ alkoxy or C₁-C₄ haloalkoxy is sub-substituted;

or

• (4) for optionally mono- to pentasubstituted, identical or differently substituted fused bi- or tricyclic radicals, which can also contain one or more heteroatoms, such as O, S or N atoms or one or more CO groups as ring members, where possible substituents:
  Halogen, nitro, cyano, C₁-C₄-alkyl, C₁-C₄-haloalkyl having 1 to 5 identical or different halogen atoms, such as fluorine and chlorine atoms, C₁-C₄-alkoxy-C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₄- haloalkoxy with 1 to 5 identical or different halogen atoms, such as fluorine and chlorine atoms, C₁-C₄-alkylthio, C₁-C₄-haloalkylthio with 1 to 5 identical or different halogen atoms, such as fluorine and chlorine atoms, C₁- C₄-alkylsulfinyl, C₁-C₄-alkylsulfonyl, hydroxy, mercapto, C₁-C₄-alkylcarbonyl, C₁-C₄-haloalkyl-carbonyl with 1 to 5 identical or different halogen atoms, such as fluorine and chlorine atoms, C₁-C₄-alkoxy-carbonyl or each optionally monosubstituted to trisubstituted, identically or differently substituted, phenyl, phenoxy, phenylthio or benzyl, the following being suitable as substituents:
  Halogen, nitro, cyano, C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₄-alkyl thio, C₁-C₄-haloalkyl with 1 to 5 identical or different halogen atoms, such as fluorine and chlorine atoms, C₁-C₄-haloalkoxy with 1 to 5 identical or different halogen atoms, such as fluorine and chlorine atoms and C₁-C₄-haloalkylthio with 1 to 5 identical or different halogen atoms, such as fluorine and chlorine atoms;

in which
R¹ for hydrogen, C₁-C₈-alkyl, C₁-C₄-haloalkyl with 1 to 5 identical or different halogen atoms, such as fluorine and chlorine atoms, for optionally mono- or polysubstituted, identically or differently, substituted by halogen or C₁-C₄-alkyl C₇-cycloalkyl or phenyl which is optionally monosubstituted to trisubstituted by identical or different substituents, halogen, C₁-C₄-alkyl or C₁-C₄-alkoxy being suitable as substituents,
R² and R³ are the same or different and represent hydrogen or C₁-C₄ alkyl;
R⁴ for C₁-C₈-alkyl, C₁-C₄-haloalkyl having 1 to 5 identical or different halogen atoms, such as fluorine and chlorine atoms, for optionally C₃-C₇- substituted one or more times, identically or differently by halogen or C₁-C₄-alkyl Cycloalkyl or phenyl which is monosubstituted to trisubstituted by identical or different substituents, halogen, C₁-C₄-alkyl or C₁-C₄-alkoxy being suitable as substituents; and
W for oxygen or one of the groupings = N-OR⁵ and
= N-NR⁶R⁷, where
R⁵ for C₁-C₆-alkyl or for optionally single to triple, identical or different by halogen, nitro, cyano, thiocarbamoyl, C₁-C₄-alkyl, C₁-C₄-haloalkyl having 1 to 5 identical or different halogen atoms, such as fluorine and Chlorine atoms, C₁-C₄-alkoxy, C₁-C₄-alkoxy-C₁-C₄-alkyl, C₁-C₄-halogen alkoxy with 1 to 5 identical or different halogen atoms, such as fluorine and chlorine atoms, C₁-C₄-alkylthio, C₁-C₄ -Halogenalkylthio with 1 to 5 identical or different halogen atoms, such as fluorine and chlorine atoms, C₁-C₄-alkylthio-C₁-C₄-alkyl, C₁-C₄-alkylsulfinyl-C₁-C₄-alkyl, C₁-C₄-alkylsulfonyl-C₁- C₄-alkyl, C₁-C₄-alkylsulfinyl, C₁-C₄-alkyl sulfonyl, C₁-C₄-haloalkylsulfonyl with 1 to 5 identical or different halogen atoms, such as fluorine and chlorine atoms, formyl, C₁-C₄-alkyl carbonyl, C₁-C₄- Alkoxy-carbonyl or C₁-C₄-alkoximino-C₁-C₄-alkyl, substituted benzyl; and
R⁶ and R⁷ are the same or different and represent hydrogen, C₁-C₆-alkyl or optionally optionally up to three times, identical or differently substituted phenyl, halogen, nitro, cyano, C₁-C₄-alkyl, C₁ being suitable as substituents - C₄-Halogen alkyl with 1 to 5 identical or different halogen atoms, such as fluorine and chlorine atoms, C₁-C₄-alkoxy or C₁-C₄-haloalkoxy with 1 to 5 identical or different halogen atoms, such as fluorine and chlorine atoms.

Q particularly preferably stands for one of the groupings

in which
Z¹, Z² and Z³ are the same or different and represent hydrogen, chlorine, bromine, nitro, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl; CH₂F, CHF₂, CF₃, CH₂Cl, CH₂Br, CHClCH₃; Methoxy, ethoxy, methoxymethyl or ethoxymethyl are available.

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

X particularly preferably represents oxygen or sulfur.

Y particularly preferably represents one of the groups

A is particularly preferred

• (1) for optionally mono- to trisubstituted, identically or differently substituted phenyl, the substituents being halogen, nitro, cyano, C₁-C₁₂-alkyl, C₁-C₁₂-haloalkyl having 1 to 5 identical or different halogen atoms, such as fluorine and chlorine atoms, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy with 1 to 5 identical or different halogen atoms, such as fluorine and chlorine atoms, C₁-C₄-alkylthio, C₁-C₄-haloalkylthio with 1 to 5 identical or different halogen atoms, such as fluorine and chlorine atoms, C₂-C₄-alkenyl, C₂-C₄-haloalkenyl having 1 to 5 identical or different halogen atoms, such as fluorine and chlorine atoms, the groupings such as
  each optionally single to triple, identical or different by halogen, nitro, cyano, thiocarbamoyl, C₁-C₄-alkyl, C₁-C₄-haloalkyl having 1 to 5 identical or different halogen atoms, such as fluorine and chlorine atoms, C₁-C₄-alkoxy , C₁-C₄-alkoxy-C₁-C₄-alkyl, C₁-C₄-haloalkoxy with 1 to 5 identical or different halogen atoms, such as fluorine and chlorine atoms, C₁-C₄-alkylthio, C₁-C₄-haloalkylthio with 1 to 5 identical or various halogen atoms, such as fluorine and chlorine atoms, C₁-C₄-alkylthio-C₁-C₄-alkyl, C₁-C₄-alkylsulfinyl-C₁-C₄-alkyl, C₁-C₄-alkylsulfonyl-C₁-C₄-alkyl, C₁-C₄- Alkylsulfinyl, C₁-C₄-alkylsulfonyl, C₁-C₄-haloalkylsulfonyl with 1 to 5 identical or different halogen atoms, such as fluorine and chlorine atoms, formyl, C₁-C₄-alkylcarbonyl, C₁-C₄-alkoxy-carbonyl, C₁-C₄-alkoximino- C₁-C₂-alkyl, optionally substituted by C₁-C₂-alkyl oxadiazol-3-yl or one of the groupings substituted phenyloxy, phenylthio, benzyloxy or pyridyloxy;
• (2) for each, if necessary, up to five times, equal to or variously substituted cyclopentyl, cyclohexyl, cyclopentenyl or cyclohexenyl, where fluorine, chlorine, bromine, Methyl, ethyl, isopropyl, methoxy or trifluoromethyl in question come,
• (3) for one of the following, optionally single or double, identical to the differently substituted heterocycles: where in each case are suitable as substituents
  Fluorine, chlorine, nitro, cyano; Methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl; Methoxy, ethoxy, n- or i-propoxy; Methylthio; -CF₃, -CHF₂, -CH₂CF₃, -CH₂-CF₂-CHF₂, -CH (CF₃) -CH₃; -OCF₃, -OCHF₂, -OCH₂CF₃, -O-CH₂-CF₂-CF₃, -OCH₂-CF₂-CHF₂, -O-CH (CF₃) -CH₃; -SCF₃;
  and in each case optionally mono- or disubstituted, identically or differently substituted phenyl, phenoxy or phenylthio, suitable substituents
  Fluorine, chlorine, nitro, cyano, methyl, ethyl, methoxy, ethoxy, methylthio, trifluoromethyl, trifluoromethoxy or trifluoromethylthio;
  and where
  R⁸ is C₁-C₄ alkyl, especially methyl or ethyl; C₁-C₄ alkylcarbonyl, especially methylcarbonyl or ethylcarbonyl; and for optionally single or double, identical or different by C₁-C₄-alkyl, in particular methyl or ethyl; Halogen, especially fluorine or chlorine; C₁-C₄ haloalkyl, especially trifluoromethyl; C₁-C₄ alkoxy, especially methoxy; and C₁-C₄ haloalkoxy, especially trifluoromethoxy substituted phenylsulfonyl;
  or
• (4) as well as for the following, arbitrarily linked and optionally mono- to tetrasubstituted, identical or differently substituted bi- or tricyclic radicals:

where in each case are suitable as substituents
Fluorine, chlorine, bromine, nitro, cyano; Methyl, ethyl; Methoxy, methylthio, trifluoromethyl, trifluoromethoxy or trifluoromethylthio;
in which
R¹ for hydrogen, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, for optionally up to five times, identically or differently, C₃-C₇- substituted by fluorine, chlorine, bromine or methyl Cycloalkyl or phenyl which is optionally monosubstituted to trisubstituted by identical or different substituents, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, methoxy or ethoxy being suitable as substituents,
R² and R³ are the same or different and represent hydrogen, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl;
R⁴ for methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, for optionally single to five times, the same or different substituted by fluorine, chlorine, bromine or methyl, C₃-C₇-cycloalkyl or represents phenyl which is monosubstituted to trisubstituted by identical or different substituents, suitable substituents
Fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, methoxy or ethoxy; and
W stands for oxygen or one of the groupings = N-OR⁵ and = N-NR⁶R⁷, where
R⁵ is C₁-C₄-alkyl or benzyl which may be monosubstituted to trisubstituted by identical or different substituents, suitable substituents
Fluorine, chlorine, bromine, cyano, nitro, trifluoromethyl, trifluoromethoxy, methylthio, methylsulfinyl, methylsulfonyl, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy or ethoxy; and
R⁶ and R⁷ are identical or different and represent hydrogen, C₁-C₄-alkyl or phenyl which is optionally monosubstituted to triple, identically or ver differently substituted by fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, trifluoromethyl, Methoxy or trifluoromethoxy come into question.

Q very particularly preferably stands for one of the groupings

in which
Z¹ and Z² are the same or different and represent hydrogen, chlorine, bromine, nitro, methyl, ethyl, methoxy or ethoxy.

R very particularly preferably represents hydrogen, methyl, ethyl, methoxy methyl, ethoxymethyl, methylcarbonyl, phenylcarbonyl or methyl sulfonyl.

X very particularly preferably represents oxygen or sulfur.

Y very particularly preferably stands for -CH₂-.

A very particularly preferably represents phenyl which is monosubstituted to trisubstituted by identical or different substituents, suitable substituents
Fluorine, chlorine, bromine, nitro, cyano, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl; Methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy; Methylthio, CF₃, OCF₃, OCHF₂, SCF₃, SCCl₂F; CH₂Br, CH₂Cl; the grouping

furthermore, if necessary, up to three times the same or different from 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-, i-, s- or t-butoxy; Methylthio, methylthiomethyl, CF3, OCF₃, OCHF₂, SCF₃, SCCl₂F; CH₂Br, CH₂Cl, methoxycarbonyl,  Methylsulfinyl, methylsulfonyl, trifluoromethylsulfonyl or the group tion

substituted phenoxy;
in which
R1 is hydrogen, methyl or ethyl;
R² and R³ are the same or different and represent hydrogen or methyl;
R⁴ represents methyl or ethyl; and
W stands for oxygen or the grouping = N-OR⁵,
in which
R⁵ stands for methyl, ethyl, n- or i-propoyl, n-, i-, s- or t-butyl or for benzyl which is monosubstituted to trisubstituted identically or differently, fluorine, chlorine, bromine as phenyl substituents, Nitro, cyano, methyl, ethyl, methoxy or ethoxy come into question.

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

in which
R, Z¹ and Z² stand for the abovementioned general, preferred, particularly preferred and particularly preferred meanings and
X¹, X², X³, X⁴ and X⁵ represent the substituents mentioned above under A in general, preferably, particularly preferably and very particularly preferably for the phenyl or phenoxy radical and
X¹, X², X³ and X⁴ can also each represent hydrogen.

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

The general or preferred areas listed above Residual definitions or explanations apply to the end products and for the Starting and intermediate products accordingly. These residual definitions can with each other, i.e. also between the respective preferred areas be combined.

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

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

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

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

Examples of the new substituted N-isothiazolyl- (thio) amides are in the Tables 1 to 9 listed:

Table 1

Compounds in Table 1 correspond to the general formula (I), in which

R = H
X = O
Y = CH₂
A = as listed below:

Table 2

Table 2 contains compounds of the general formula (I), in which
Y = CH (CH₃)
Q, R, X and A = as listed in Table 1.

Table 3

Table 3 contains compounds of the general formula (I), in which

R, X, Y and A = as listed in Table 1.

Table 4

Table 4 contains compounds of the general formula (I), in which
X = S
Q, R, Y and A = as listed in Table 3.

Table 5

Table 5 contains compounds of the general formula (I), in which

R, X, Y and A = as listed in Table 1.  

Table 6

Table 6 contains compounds of the general formula (I), in which

R, X, Y and A = as listed in Table 1.

Table 7

Table 7 contains compounds of the general formula (I), in which

R, X, Y and A = as listed in Table 1.

Table 8

Table 8 contains compounds of the general formula (I), in which
R = H
X = O
Y = CH₂

Q = as listed below:

Table 9

Table 9 contains compounds of the general formula (I), in which

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

Is used in the preparation of compounds of the formula (Ia) according to Method (a) z. B. Thieno [2,3c] isothiazol-3-yl-amine and [4- (4-cyanophenoxy)] phenyl-acetic acid chloride as starting materials, so the course of the reaction can the following reaction scheme can be reproduced:

Is used in the preparation of compounds of the formula (Ib) according to Method (b) z. B. Thieno [2,3c] isothiazol-3-yl- [4- (4-nitrophenoxy)] phenylacetyl amine as starting material and Lawesson's reagent (2,4-bis- (4-methoxyphenyl) -1,3- dithia-2,4-diphosphetane-2,4-disulfide) as a sulfurizing agent, so the reac can be reproduced by the following reaction scheme:

Is used in the preparation of compounds of the formula (Ib) according to Method (c) z. B. Thieno [2,3c] isothiazol-3-yl-amine and [4- (4-chlorophenoxy)] phenyl-dithioacetic acid methyl ester as starting materials, the reaction can run through the following reaction scheme:

The starting materials in processes (a) and (c) according to the invention Aminoisothiazoles of the formula (II) using are known (cf. e.g. GB 1568377; J. Chem. Res. Synop. 1989, 29; DE-A 27 13 573; Can. J. Chem. 1973 (51), 1742 or JP 05070469) and / or can be prepared by known methods produce (see e.g. the above-mentioned references).

They can also be obtained by e.g. B. aminonitrile derivatives of the formula (V)

in which
Het has the meaning given above,
first reacted with hydrogen sulfide in the presence of a base, such as pyridine or triethylamine;
and the thioamide derivatives of the formula (VI) thus obtained

in which
Het has the meaning given above,
then reacted oxidatively with an oxidizing agent such as H₂O₂, bromine or sodium hypochlorite.

The aminonitrile derivatives of the formula (V) are known (cf., for example, EP-A 0 453 611; Acta Chim. Scand., Ser. B. 1975, B 29 (2), 224; DE-A 27 13 573; Chem. Pharm. Bull. 1971, 19, 119; Tetrahedron Letters, 1989, 30, 2631; J. Chem. Soc., Perkins Trans I, 1987, 1521; Hely. 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 are Establish known methods (see e.g. the literature references mentioned above).

The further starting materials in process (a) according to the invention Acid halides of the formula (III) are generally known verbs organic chemistry. In formula (III), Hal preferably represents Chlorine or bromine.

The further as starting materials in process (c) according to the invention Dithioesters of the formula (IV) using are known (cf., for example, tetrahedron 2663 (1984) or J. Chem. Research (M) 2701 (1988)) and / or can be adjusted produce known, analogous processes. Alk is present in the formula (IV) preferably for methyl.

Suitable diluents for carrying out the inventive Process (a) preferably optionally halogenated aliphatic or aroma table hydrocarbons, ethers or nitriles such as. B. cyclohexane, toluene, chlorine  benzene, chloroform, dichloromethane, dichloroethane, dioxane, tetrahydrofuran, di ethyl ether or acetonitrile in question.

All conventional proton acceptors can be used as bases in process (a) will. Alkali or alkaline earth metal hydroxides, alkali metal or alkaline earth carbonates or bicarbonates or nitrogen bases. Called Examples include sodium hydroxide, calcium hydroxide, potassium carbonate, Sodium hydrogen carbonate, triethylamine, dibenzylamine, diisopropylamine, pyridine, Quinoline, diazabicyclooctane (DABCO), diazabicyclonones (DBN) and diaza bicycloundecen (DBU).

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

When carrying out process (a), it is generally used per mole Aminoisothiazole of formula (II) 1 to 2 mol, preferably 1 to 1.5 mol Acid halide of the formula (III).

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

The sulfurizing agents used in carrying out the invention Process (b) preferably in question: phosphorus pentasulfide or Lawesson reagent [2,4-bis (4-methoxyphenyl) -1,3,2,4-dithiadiphosphetane-2,4-dithione] (cf. also Tetrahedron Vol. 41, No. 22, 5061 ff (1985)).

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

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

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

Suitable diluents for carrying out the inventive Process (c) all common solvents in question. Are preferably usable optionally halogenated aliphatic or aromatic hydrocarbons, such as Methylene chloride, dichloroethane, cyclohexane, toluene or chlorobenzene.

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

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

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

The active ingredients are suitable for good plant tolerance and cheaper Warmblood toxicity to control animal pests, in particular Insects, arachnids and nematodes, which are used in agriculture, in forests, in Storage and material protection as well as in the hygiene sector. she can preferably be used as pesticides. You are against normally sensitive and resistant species as well as against all or individual developments Stages effective. The pests mentioned above include:

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

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

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

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

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

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

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

From the order of the Dermaptera z. B. Auricular Forficula.

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

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

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

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

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

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

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

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

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

From the order of the Diptera z. B. Aedes spp., Anopheles spp., Culex spp.,

Drosophila melanogaster, Musca spp., Fannia spp., Calliphora erythrocephala, Lucilia spp., Chrysomyia spp., Cuterebra spp., Gastrophilus spp., Hyppobosca spp., Stomoxys spp., Oestrus spp., Hypoderma spp., Tabanus spp., Tannia spp., Bibio hortulanus, Oscinella frit, Phorbia spp., Pegomyia hyoscyami, Ceratitis capitata, Dacus oleae, Tipula paludosa.

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

From the order of Acarina z. B. Acarus siro, Argas spp., Ornithodoros spp., Dermanyssus gallinae, Eriophyes ribis, Phyllocoptruta oleivora, Boophilus spp., Rhipicephalus spp., Amblyomma spp., Hyalomma spp., Ixodes spp., Psoroptes spp., Chorioptes spp., Sarcoptes spp., Tarsonemus spp., Bryobia praetiosa, Panonychus spp., Tetranychus spp.

The plant parasitic nematodes include z. B. Pratylenchus spp., Radopho lus similis, Ditylenchus dipsaci, Tylenchulus semipenetrans, Heterodera spp., Globodera spp., Meloidogyne spp., Aphelenchoides spp., Longidorus spp., Xiphinema spp., Trichodorus spp.

The compounds of the formula (I) according to the invention are particularly noteworthy characterized by excellent insecticidal activity.

They can be used to control plants with particularly good success use harmful insects. They have a strong impact, for example against horseradish leaf beetle larvae (Phaedon cochleariae), caterpillars of the owl butterfly (Spodoptera frugiperda) and against the green rice leafhopper (Nephotettix cincticeps).

The active ingredients can be converted into the usual formulations, such as Lö solutions, emulsions, wettable powders, suspensions, powders, dusts, pastes, sol Liche powder, granules, suspension emulsion concentrates, active ingredient impregnated nated natural and synthetic substances as well as very fine encapsulation in polymers Fabrics.  

These formulations are prepared in a known manner, e.g. Federation preferably by mixing the active ingredients with extenders, i.e. liquid Solvents and / or solid carriers, optionally using of surface-active agents, i.e. emulsifiers and / or dispersants and / or foam-generating agents.

In the case of the use of water as an extender, e.g. B. also organic Solvents are used as auxiliary solvents. As a liquid solvent essentially come into question: aromatics, such as xylene, toluene, or Alkylnaphthalenes, chlorinated aromatics and chlorinated aliphatic hydrocarbons substances such as chlorobenzenes, chlorethylenes or methylene chloride, aliphatic Koh hydrogen, such as cyclohexane or paraffins, e.g. B. petroleum fractions, mineral and vegetable oils, alcohols, such as butanol or glycol, and their ethers and Esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclo hexanone, strongly polar solvents such as dimethylformamide and dimethyl sulfoxide, and water.

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

In the formulations, adhesives such as carboxymethyl cellulose, ver natural and synthetic polymers in powder, granular or latex form be used, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, and na natural phospholipids such as cephalins and lecithins and synthetic phos pholipid. Other additives can be mineral and vegetable oils.  

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

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

The active ingredient according to the invention can be in its commercially available formulations as well as in the use forms prepared from these formulations in Mix with other active ingredients, such as insecticides, attractants, sterilants, Bactericides, acaricides, nematicides, fungicides, growth regulators Substances or herbicides are present. Insecticides include, for example Phosphoric acid esters, carbamates, carboxylic acid esters, chlorinated hydrocarbons, Phenylureas, substances produced by microorganisms u. a.

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

Fungicides

2-aminobutane; 2-anilino-4-methyl-6-cyclopropyl-pyrimidine; 2 ′, 6′-dibromo-2-methyl-4′-trifluoromethoxy-4′-trifluoromethyl-1,3-thiazole-5-carboxanide; 2,6-di chloro-N- (4-trifluoromethylbenzyl) benzamide; (E) -2-methoxyimino-N-methyl-2- (2-phenoxyphenyl) acetamide; 8-hydroxyquinoline sulfate; Methyl- (E) -2- {2- [6- (2-cyanophenoxy) pyrimidin-4-yloxy] phenyl} -3-methoxyacrylate; Methyl (E) methoximino [alpha- (o-tolyloxy) -o-tolyl] acetate; 2-phenylphenol (OPP), aldimorph, ampropylfos, anilazine, azaconazole,
Benalaxyl, Benodanil, Benomyl, Binapacryl, Biphenyl, Bitertanol, Blasticidin-S, Bromuconazole, Bupirimate, Buthiobate,
Calcium polysulfide, captafol, captan, carbendazim, carboxin, quinomethionate (quinomethionate), chloroneb, chloropicrin, chlorothalonil, chlozolinate, cufraneb, cymoxanil, cyproconazole, cyprofuram,
Dichlorophene, diclobutrazole, diclofluanid, diclomezin, dicloran, diethofencarb, difenoconazole, dimethirimol, dimethomorph, diniconazole, dinocap, diphenylamine, dipyrithione, ditalimfos, dithianon, dodine, drazoxolone,
Edifenphos, epoxyconazole, ethirimol, etridiazole,
Fenarimol, Fenbuconazole, Fenfurropan, Fenpiclonil, Fenpropidin, Fenpropimorph, Fentinacetat, Fentinhydroxyd Ferbam, Ferimzone, Fluazinam, Fludioxonil, Fluoromide, Fluquinconazole, Flusilazole, Flusulfamide, Flutolanil, Futuberfoxylol ,
Guazatine,
Hexachlorobenzene, hexaconazole, hymexazole,
Imazalil, Imibenconazol, Iminoctadin, Iprobefos (IBP), Iprodione, Isoprothiolan,
Kasugamycin, copper preparations such as: copper hydroxide, copper naphthenate, copper oxychloride, copper sulfate, copper oxide, oxine-copper and Bordeaux mixture,
Mancopper, Mancozeb, Maneb, Mepanipyrim, Mepronil, Metalaxyl, Metconazol, Methasulfocarb, Methfuroxam, Metiram, Metsulfovax, Myclobutanil,
Nickel dimethyldithiocarbamate, nitrothal isopropyl, Nuarimol,
Ofurace, oxadixyl, oxamocarb, oxycarboxin,
Pefurazoate, penconazole, pencycuron, phosdiphen, phthalide, pimaricin, piperalin, polycarbamate, polyoxin, probenazole, prochloraz, procymidon, propamocarb, propiconazole, propineb, pyrazophos, pyrifenox, pyrimethanil, pyroquilon,
Quintozen (PCNB),
Sulfur and sulfur preparations,
Tebuconazole, tecloftalam, tecnazene, tetraconazole, thiabendazole, Thicyofen, thiophanate-methyl, thiram, Tolclophos-methyl, tolylfluanid, triadimefon, triadimenol, triazoxide, Trichlamid, tricyclazole, tridemorph, triflumizole, triforine, triticonazole,
Validamycin A, vinclozolin,
Zineb, ziram

Bactericides

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

Insecticides / acaricides / nematicides

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

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

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

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

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

When used against hygiene and storage pests, the stands out Active ingredient through an excellent residual effect on wood and clay as well due to good stability to alkali on limed substrates.

The active compounds according to the invention act not only against plant, hygiene and stored-product pests, but also in the veterinary sector against animal parasites (ectoparasites) such as tick ticks, leather ticks, mites, running mites, flies (stinging and licking), parasitic fly larvae, lice, hair lice, Featherlings and fleas. These parasites include:
From the order of the Anoplurida z. B. Haematopinus spp., Linognathus spp., Pediculus spp., Phtirus spp., Solenopotes spp.

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

From the order Diptera and the subordinates Nematocerina as well Brachycerina e.g. B. Aedes spp., Anopheles spp., Culex spp., Simulium spp., Eusimulium spp., Phlebotomus spp., Lutzomyia spp., Culicoides spp., Chrysops spp., Hybomitra spp., Atylotus spp., Tabanus spp., Haematopota spp., Philipomyia spp., Braula spp., Musca spp., Hydrotaea spp., Stomoxys spp., Haematobia spp.,  Morellia spp., Fannia spp., Glossina spp., Calliphora spp., Lucilia spp., Chrysomyia spp., Wohlfahrtia spp., Sarcophaga spp., Oestrus spp., Hypoderma spp., Gasterophilus spp., Hippobosca spp., Lipoptena spp., Melophagus spp.

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

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

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

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

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

The active compounds of the formula (I) according to the invention are also suitable for Combating arthropods that farm livestock, such as B. cattle, Sheep, goats, horses, pigs, donkeys, camels, buffaloes, rabbits, chickens, Turkeys, ducks, geese, bees, other pets such as B. dogs, cats, House birds, aquarium fish and so-called experimental animals, such as B. hamsters, Infest guinea pigs, rats and mice. By fighting this Arthropods are said to cause deaths and reduced performance (in meat, milk, Wool, skins, eggs, honey, etc.) can be reduced, so that through the use the active ingredients according to the invention a more economical and simple animal neck tion is possible.  

The active compounds according to the invention are used in the veterinary sector in a known manner by enteral administration in the form of, for example, Tab Latvian, capsules, watering, drenching, granules, pastes, boluses, the feed-through process, of suppositories, by parenteral administration, such as by injections (intramuscular, subcutaneous, intravenous, intraperitoneal, etc.), Implants, by nasal application, by dermal application in the form for example diving or bathing (dipping), spraying (spray), pouring on (Pour-on and spot-on), washing, powdering and with the help of molded articles containing active ingredients, such as collars, ear tags, tail tags, Limb straps, holsters, marking devices etc.

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

It has also been found that the compounds of the formula (I) show a high insecticidal activity against insects, the technical Destroy materials.

The following insects may be mentioned by way of example and preferably, but without limitation:
Beetle like
Hylotrupes bajulus, Chlorophorus pilosis, Anobium punctatum, Xestobium rufovillosum, Ptilinus pecticornis, Dendrobium pertinex, Ernobius mollis, Priobium carpini, Lyctus brunneus, Lyctus africanus, Lyctus planicollis, Lyctus linearesces rugus, Lyctus pubescescus, Lyctus pubis linearis, Lyctus linearesces rug Xyleborus spec. Tryptodendron spec. Apate monachus, Bostrychus capucins, Heterobostrychus brunneus, Sinoxylon spec. Dinoderus minutus
Skin wings like
Sirex juvencus, Urocerus gigas, Urocerus gigas taignus, Urocerus augur
Termites like
Kalotermes flavicollis, Cryptotermes brevis, Heterotermes indicola, Reticulitermes flavipes, Reticulitermes santonensis, Reticulitermes lucifugus, Mastotermes darwiniensis, Zootermopsis nevadensis, Coptotermes formosanus.

Bristle tails, such as Lepisma saccarina.

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

It is very particularly preferred to prevent insect attack protective material around wood and wood processing products.

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

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

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

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

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

An organic chemical solvent serves as the solvent and / or diluent solvent or solvent mixture and / or an oily or oily heavy volatile organic chemical solvent or solvent mixture and / or a polar organic chemical solvent or solvent combination mixed and / or water and optionally an emulsifier and / or wetting agent.

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

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

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

The organic non-volatile oily or oily solvents with a Evaporation rate above 35 and a flash point above 30 ° C, preferably above 45 ° C, can be caused in part by easily or moderately volatile organic chemical solvents are replaced, provided that the solvent mix also an evaporation number above 35 and a flash point above  30 ° C, preferably above 45 ° C, and that the insecticide-fungicide mixture is soluble or emulsifiable in this solvent mixture.

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

As an organic chemical binder in the present Er finding the known water-dilutable and / or in the used organic chemical solvents soluble or dispersing or emul gable synthetic resins and / or binding drying oils, especially binders consisting of or containing an acrylic resin, a vinyl resin, e.g. B. polyvinyl acetate, Polyester resin, polycondensation or polyaddition resin, polyurethane resin, alkyd resin or modified alkyd resin, phenolic resin, hydrocarbon resin such as indene-coumarone resin, Silicone resin, drying vegetable and / or drying oils and / or physically drying binders based on a natural and / or Resin used.

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

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

The binder mentioned can be wholly or partly by a fixation medium (mixture) or a plasticizer (mixture) can be replaced. These additions should volatilize the active ingredients and crystallize or from  prevent falling. They preferably replace 0.01 to 30% of the binder (based on 100% of the binder used).

The plasticizers come from the chemical classes of phthalic acid esters such as Dibutyl, dioctyl or benzyl butyl phthalate, phosphoric acid esters such as tributyl phosphate, adipic acid esters such as di- (2-ethylhexyl) adipate, stearates such as butyl stearate or amyl stearate, oleates such as butyl oleate, glycerol ether or higher molecular weight Gly kolether, glycerol ester and p-toluenesulfonic acid ester.

Fixing agents are chemically based on polyvinyl alkyl ethers such as. B. Polyvinyl methyl ether or ketones such as benzophenone, ethylene benzophenone.

Water is also particularly suitable as a solvent or diluent, optionally in a mixture with one or more of the above organic chemical solvents or diluents, emulsifiers and dispersers gators.

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

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

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

Insecticides such as chlorine are particularly preferred as admixing partners pyriphos, phoxim, silafluofin, alphamethrin, cyfluthrin, cypermethrin, delta methrin, permethrin, imidacloprid, NI-25, flufenoxuron, hexaflumuron and tri flumuron, and fungicides such as epoxyconazole, hexaconazole, azaconazole, Propiconazole, tebuconazole, cyproconazole, metconazole, imazalil, Dichlorofluoride, tolylfluanid, 3-iodo-2-propynyl butyl carbamate, N-octyl-isothiazolin-3-one and 4,5-dichloro-N-octylisothiazolin-3-one.

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

Manufacturing examples example 1

(Method a)

To a solution of 1.60 g (0.01 mol) of thieno [2,3c] isothiazol-3-yl-amine in 15 ml Pyrimidine and 50 ml acetonitrile is a solution of 3.50 g (0.012 mol) [4- (4- Nitrophenoxy)] - phenylacetic acid chloride added dropwise in 20 ml of acetonitrile. You stir 18 hours at 25 ° C and then concentrated to dryness. The reaction Mixture is taken up in water / ethyl acetate and the organic phase more times washed with 10% sodium hydroxide solution. After drying and concentrating a viscous residue, which is obtained by chromatography on silica gel Methylene chloride / ethyl acetate (20: 1) is cleaned as the eluent.

0.24 g (20% of theory) of thieno [2,3c] isothiazol-3-yl- [4- (4-nitro phenoxy)] phenylacetylamine with a melting point of 223 ° C.

Analogously or according to the general information on the preparation, the the following compounds of formula (I):

Examples of use Example A Phaedon larval test

Solvent: 7 parts by weight of dimethylformamide
Emulsifier: 1 part by weight of alkylaryl polyglycol ether
To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amount of solvent and the stated amount of emulsifier, and the concentrate is diluted with water to the desired concentration.

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

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

In this test, z. B. the connection of preparation example 2 an exemplary active ingredient concentration of 0.1%, a kill of 100% after 7 days.  

Example B Spodoptera Frugiperda test

Solvent: 7 parts by weight of dimethylformamide
Emulsifier: 1 part by weight of alkylaryl polyglycol ether
To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amount of solvent and the stated amount of emulsifier, and the concentrate is diluted with water to the desired concentration.

Cabbage leaves (Brassica oleracea) are dipped into the active ingredient preparation the desired concentration and treated with caterpillars of the owl butterfly (Spodoptera frugiperda) occupied while the leaves are still moist.

After the desired time, it is determined in%. 100% means that all caterpillars have been killed; 0% means that no caterpillars have been killed.

In this test, z. B. the connection of preparation example 2 an exemplary active ingredient concentration of 0.1% a kill of 100% after 7 days.  

Example C Nephotettix test

Solvent: 7 parts by weight of dimethylformamide
Emulsifier: 1 part by weight of alkylaryl polyglycol ether
To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amount of solvent and the stated amount of emulsifier, and the concentrate is diluted with water to the desired concentration.

Rice seedlings (Oryza sativa) are dipped into the active ingredient preparation the desired concentration and treated with green rice leafhopper larvae (Nephotettix cincticeps) occupied while the seedlings are still moist.

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

In this test, z. B. the connection of preparation example 2 an exemplary active ingredient concentration of 0.1% a kill of 100% after 6 days.

Claims (7)

1. Compounds of formula (I) in which
Q for grouping stands,
in which
Het represents an optionally substituted heterocycle,
R represents hydrogen, alkyl, haloalkyl, alkoxyalkyl, alkylcarbonyl, alkylsulfonyl, in each case optionally substituted arylcarbonyl, arylsulfonyl or arylalkyl or optionally substituted cycloalkyl,
X represents oxygen or sulfur,
Y represents optionally substituted alkylene, alkenylene, alkyleneoxy or alkylene thio and
A represents optionally substituted aryl, optionally substituted cycloalkyl, optionally substituted cycloalkenyl or an optionally substituted heterocycle. 2. A process for the preparation of compounds of formula (I) according to claim 1, characterized in that

• a) the new substituted N-isothiazoiyl amides of the formula (Ia) in which
  Q, R, Y and A have the meaning given above,
  obtained when aminoisothiazoles of the formula (II) in which
  Q and R have the meaning given above,
  with acid halides of the formula (III) Hal-CO-YA (III) in which
  Y and A have the meaning given above and
  Hal stands for halogen,
  in the presence of a base and in the presence of a diluent;
  or
• b) the new substituted N-isothiazolyl-thioamides of the formula (Ib) in which
  Q, R, Y and A have the meaning given above,
  obtained if the N-isothiazolylamides of the formula (Ia) obtainable according to process (a) in which
  Q, R, Y and A have the meaning given above,
  with a sulfurizing agent, optionally in the presence of a diluent;
  or
• c) the new substituted N-isothiazolyl-thioamides of the formula (Ib) in which
  Q, R, Y and A have the meaning given above,
  obtained when aminoisothiazoles of the formula (II) in which
  Q and R have the meaning given above,
  with dithioesters of the formula (IV) in which
  Y and A have the meaning given above and
  Alk stands for alkyl or the group MO-CO-CH₂-, where M stands for an alkali metal (such as sodium or potassium),
  if appropriate in the presence of a diluent.

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