WO1998005670A1

WO1998005670A1 - Substituted n-isothiazolyl-(thio)amides

Info

Publication number: WO1998005670A1
Application number: PCT/EP1997/003858
Authority: WO
Inventors: Markus Heil; Thomas Bretschneider; Gerd Kleefeld; Christoph Erdelen
Original assignee: Bayer Aktiengesellschaft
Priority date: 1996-07-31
Filing date: 1997-07-18
Publication date: 1998-02-12
Also published as: BR9710897A; KR20000029574A; EP0915887A1; DE19630814A1; CN1232464A; IL128098A0; AU3940397A; JP2000515530A

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 new N-isothiazolyl (thio) amides, several processes for their preparation and their use for controlling animal pests.

It is already known that certain N-isothiazolylamide derivatives have insecticidal properties (cf. e.g. EP-A 0 623 282 and WO-A 95/31448).

The level and / or duration of action of these previously known compounds is, however, not completely satisfactory in all areas of application, in particular against certain organisms or at low application concentrations

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

Q-N-C - Y-A (I) l R

in which

QO for the G Grruuppppiieerruunngg

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 for optionally substituted alkylene, alkenylene, alkyleneoxy or

Alkylenthio stands 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 substituted N-isothiazolyl amides of the formula (Ia)

O Q -N -C - Y-A (Ia)

I R

in which

Q, R, Y and A have the meaning given above,

obtained when aminoisothiazoles of the formula (II)

Q-N -H (II) i R

in which

Q and R have the meaning given above,

with acid halides of the formula (III)

Hal-CO-Y-A (III)

in which

Y and A have the meaning given above and

Shark represents halogen, in the presence of a base and in the presence of a diluent,

and

b) the substituted N-isothiazolyl-thioamides of the formula (Ib)

S

II

Q - -N-C -Y- (Ib)

in which

Q, R, Y and A have the meaning given above,

obtained when 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;

and

c) the substituted N-isothiazolyl-thioamides of the formula (Ib)

QNCYA (Ib) i R in which Q, R, Y and A have the meaning given above,

also obtained if aminoisothiazoles of the formula (II)

Q -N-H (H) i R

in which

Q and R have the meaning given above,

with dithioesters of the formula (IV)

S

II

Alk S-C -Y-A (IV)

in which

Y and A have the meaning given above and

Alk stands for alkyl or the group MO-CO-CH -, -, 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 the formula (I) are very good for combating animal pests, in particular insects, arachnids and nematodes, which are used in agriculture, in forestry, in the protection of stocks and materials as well as in the hygiene sector are suitable.

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 differently substituted 5- or 6-membered heterocycle having 1 or 2 heteroatoms, such as N, S and O atoms, the substituents being

Halogen, C * -C ₄ alkyl, C * -C ₄ alkoxy C * -C ₄ haloalkyl with 1 to 5 identical or different halogen atoms, such as fluorine, chlorine and bromine atoms, C _r C ₄ alkoxy-C _r C ₄ -alkyl nitro, C, -C ₄ -alkylsulfonyl, C, -C ₄ -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, C * -C ₄ -alkyl C, -C ₄ -haloalkyl having 1 to 5 identical or different halogen atoms, such as fluorine and chlorine atoms, C, -C ₄ -alkoxy-C _r C -alkyl, C , -C ₄ alkyl carbonyl,

C, -C ₄ -Alkylsulfonyl, each optionally monosubstituted to trisubstituted, identically or differently, phenylcarbonyl, phenylsulfonyl or benzyl, the substituents in each case being halogen, nitro, cyano, C * -C ₄ -alkyl, C * -C *, - Haloalkyl with 1 to 5 identical or different halogen atoms, such as fluorine and

Chlorine atoms, C, -C ₄ -alkoxy, C.-C ₄ -Alkylthιo, C.-C -, - haloalkoxy with 1 to 5 identical or different halogen atoms, such as fluorine and chlorine atoms or C _j -C ₂ -haloalkylthιo with 1 up to 5 identical or different halogen atoms, such as fluorine and chlorine atoms, or for optionally single to triple, identical or different, substituted by C, -C ₄ alkyl or halogen, C, -C ₆ cycloalkyl

X preferably represents oxygen or sulfur Y preferably represents C, -C ₆ -alkylene, C, -C ₆ -hydroxyalkylene, C, -C ₄ -alkoxy-

C - C ₆ -alkylene, C _j -C ^ alkylcarbonyloxy-C Cs-alkylene, cyano-C _r C ₆ -alkylene, C _r C ₄ -halogenated alkylene with 1 to 5 identical or different halogen atoms, such as fluorine and Chlorine atoms; optionally one to three times, identical or different substituted by fluorine, chlorine or methyl

C ₃ -C ₆ cycloalkyl-C, -C ₄ -alkylene, C ₂ -C ₄ -alkenylene, C, -C ₄ -alkyleneoxy or C _r C ₄ -alkylene thio.

A is preferred

(1) for optionally monosubstituted to trisubstituted, identically or differently, phenyl, the following being suitable as substituents:

Halogen, nitro, cyano, C, -C, ₂ -alkyl, C _r C ₁₂ -haloalkyl with 1 to 5 identical or different halogen atoms, such as fluorine and chlorine atoms, C - C _{] 2} -alkoxy, C.-C _{] 2} -Halogenalkoxy with 1 to 5 identical or different halogen atoms, such as fluorine and chlorine atoms, C, -C _{] 2} -alkylthio, C.-C ^ -Halogenalkylthio with 1 to 5 identical or different halogen atoms, such as fluorine and chlorine atoms , C ₂ -C ₁₂ alkenyl, C ₂ -C ₁₂ haloalkenyl having 1 to 5 identical or different halogen atoms, such as fluorine and chlorine atoms, optionally monosubstituted to triple, identical or different, substituted by C, -C ₄ alkyl or halogen C ₃ -C ₈ cycloalkyl, the groupings

W W

"1 7 ^■ . H Λ

- C- R - 0-CR ² R - CR ⁴

, such as

each optionally single to triple, identical or different, by halogen, nitro, cyano, thiocarbamoyl, C _r C ₄ alkyl, C _r C ₄ - haloalkyl having 1 to 5 identical or different halogen atoms, such as fluorine and chlorine atoms, C _] -C ₄ -alkoxy, C, -C ₄ -alkoxy- C, -C ₄ -alkyl, C, -C ₄ -haloalkoxy with 1 to 5 identical or different halogen atoms, such as fluorine and chlorine atoms, C _r C ₄ - alkylthio, C _r C ₄ haloalkylthio with 1 to 5 identical or different halogen atoms, such as fluorine and chlorine atoms, C _r C ₄ -

Alkylthio-C, -C ₄ -alkyl, C, -C ₄ -AlkylsuIfιnyl-C _r C ₄ -alkyl, C, -C ₄ - alkylsulfonyl-C _r C ₄ -alkyl, C _r C ₄ -alkylsulfinyl, C _r C ₄ -alkyl sul- fonyl, C, -C ₄ haloalkylsulfonyl with 1 to 5 identical or different halogen atoms, such as fluorine and chlorine atoms, formyl, C, -C ₄ alkylcarbonyl, C * -C ₄ alkoxycarbonyl, C, -C ₄ - Alkoxιmιno- C, -C ₄ alkyl, optionally substituted by C, -C ₄ alkyl substituted oxadiazolyl or one of the groupings

W W

"1, ιι.

- C - R od, er - 0-CR ² R - C- R ⁴

substituted phenyl, phenyoxy, phenylthio, benzyl, benzyloxy, pyπdyloxy, pyπmidyloxy, pyrazinyloxy or pyπdazinyloxy,

(2) for optionally mono- to pentasubstituted, identically or differently substituted CC ₈ -cycloalkyl or C -C ₈ -cycloalkenyl, where as

Substituents C _r C ₄ alkyl, C _r C ₄ haloalkyl with 1 to 5 identical or different halogen atoms, such as fluorine and chlorine atoms, C, -C ₄ alkoxy, C - C ₄ haloalkoxy with 1 to 5 identical or various halogen atoms, such as fluorine and chlorine atoms, C ₃ -C ₈ cycloalkyl, and optionally single to triple, identical or different by halogen, cyano, nitro, C, -C ₄ alkyl, C _r C ₄ - haloalkyl with 1 to 5 identical or different halogen atoms, such as fluorine and chlorine atoms, C _] -C ₄ -alkoxy, or C * -C ₄ - haloalkoxy with 1 to 5 identical or different halogen atoms, such as fluorine and chlorine atoms, substituted phenyl in

Question come

(3) for an optionally mono- to trisubstituted, identically or 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 or CS groups as ring members, where substituents come into question halogen, nitro, cyano, C _r C ₄ alkyl, C _r C ₄ alkoxy, C, -C ₄ alkyl thio, C _j -C ₄ haloalkyl with 1 up to 5 identical or different halogen atoms, such as fluorine and chlorine atoms, C _r C ₄ -haloalkoxy with 1 to 5 identical or different halogen atoms, such as fluorine and chlorine atoms, C, -C ₄ -haloalkylthio with 1 to 5 identical or different halogen atoms, such as fluorine and chlorine atoms or because optionally phenyl, phenoxy, phenylthio or benzyl which is monosubstituted or disubstituted in the same or different ways, substituents being suitable

Halogen, nitro, cyano, C _r C ₄ alkyl, C, -C ₄ alkoxy, C _r C ₄ alkyl thio, C _j - _j haloalkyl with 1 to 5 identical or different

Halogen atoms, such as fluorine and chlorine atoms, C, -C ₄ -haloalkoxy with 1 to 5 identical or different halogen atoms, such as fluorine and chlorine atoms and C, -C ₄ -haloalkylthio with 1 to 5 identical or different halogen atoms, such as fluorine and Chlorine atoms, and one optionally present in the heterocycle

NH group can be substituted for the hydrogen atom by C, -C ₆ alkyl, C, -C ₆ alkylcarbonyl or phenylsulfonyl, which in turn may optionally be substituted by C- -C ₆ alkyl, halogen, C, -C ₄ haloalkyl 1 to 5 identical or different halogen atoms, such as fluorine or chlorine atoms, C, -C ₄ alkoxy or C, -C ₄ -

Halogenalkoxy is substituted with 1 to 5 identical or different halogen atoms, such as fluorine or chlorine atoms,

or

(4) for optionally monosubstituted to pentasubstituted, identically or differently substituted fused bi- or tπcychsche residues, 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 come into question as substituents

Halogen, nitro, cyano, C _] -C ₄ alkyl, C * -C ₄ haloalkyl having 1 to 5 identical or different halogen atoms, such as fluorine and

Chlorine atoms, C, -C ₄ -alkoxy-C * -C ₄ -alkyl, C * -C ₄ -alkoxy,, -C ₄ - haloalkoxy with 1 to 5 identical or different halogen atoms, such as fluorine and chlorine atoms, C _j - C ₄ -Alkylthιo, C * -C ₄ - haloalkylthio with 1 to 5 identical or different halogen atoms, such as fluorine and chlorine atoms, C, -C ₄ -alkylsulfinyl, C _r C ₄ -

Alkylsulfonyl, hydroxy, mercapto, C, -C ₄ -alkylcarbonyl C ^ C-- haloalkyl-carbonyl with 1 to 5 identical or different halogen atoms, such as fluorine and chlorine atoms, C, -C ₄ -alkoxy-carbonyl or in each case simply until triple, equal or different different, especially in the phenyl part substituted phenyl, phenoxy, phenylthio or benzyl, the following being suitable as substituents: halogen, nitro, cyano, C, -C ₄ -alkyl, C, -C ₄ -alkoxy, C _r C ₄ -alkyl- thio, C.-C ₄ -haloalkyl having 1 to 5 identical or different halogen atoms, such as fluorine and chlorine atoms, C * -C ₄ -haloalkoxy having 1 to 5 identical or different halogen atoms, such as fluorine and chlorine atoms and C _r C ₄ -Halogenalkylthio with 1 to 5 identical or different halogen atoms, such as fluorine and chlorine atoms;

in which

R ¹ for hydrogen, C, -C ₈ alkyl, C, -C ₄ haloalkyl with 1 to

5 identical or different halogen atoms, such as fluorine and chlorine atoms, for optionally mono- or polysubstituted, identically or differently, C ₃ -C ₇ -cycloalkyl substituted by halogen or C _r C ₄ -alkyl or for optionally single to triple, identical or different substituted

Phenyl, where ₄ alkoxy, suitable substituents are halogen, C _r C ₄ alkyl or C, -C into question,

R "and R ^{" 1 are the} same or different and are hydrogen or C, -C ₄ alkyl;

R ⁴ for C _r C ₈ -alkyl, C, -C ₄ -haloalkyl having 1 to 5 identical or different halogen atoms, such as fluorine and chlorine atoms, for optionally single or multiple, identical or different, by halogen or C * -C ₄ - Alkyl substituted C ₃ -C ₇ cycloalkyl or phenyl which is optionally monosubstituted to triple, identical or differently substituted, halogen, C, -C ₄ alkyl or C, -C ₄ alkoxy being suitable as substituents; and

W stands for oxygen or one of the groupings = N-OR ^≤ and = N-NR ⁶ R ⁷ , where

R ⁵ for C * -C ₆ alkyl or for optionally single to triple, identical or different, by halogen, Nitro, cyano, thiocarbamoyl, C, -C ₄ alkyl, C _r C ₄ - haloalkyl with 1 to 5 identical or different halogen atoms, such as fluorine and chlorine atoms, C _| -C ₄ - alkoxy, C _r C ₄ -alkoxy-C _r C ₄ -alkyl, C, -C ₄ -halogenated 5 alkoxy with 1 to 5 identical or different

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

10 alkyl sulfonyl C _r C ₄ alkyl, C ₄ -C ₄ alkyl sulfonyl C _r

C ₄ -alkyl, C, -C ₄ -alkylsulfonyl, C * -C ₄ -alkylsulfonyl, C - C ₄ -haloalkylsulfonyl having 1 to 5 identical or different halogen atoms, such as fluorine and chlorine atoms, formyl, C * - C ₄ alkylcarbonyl, C, -C ₄ -

15 alkoxy-carbonyl or C, -C ₄ -alkoxιmιno-C _] -C -alkyl substituted benzyl, and

R ⁶ and R ^{7 are the} same or different and are hydrogen, C, -C ₆ -alkyl or phenyl which is monosubstituted to trisubstituted by identical or different means

20 are available, which are suitable as substituents

Halogen, nitro, cyano, C * -C ₄ alkyl, C _r C ₄ halogen alkyl with 1 to 5 identical or different halogen atoms, such as fluorine and chlorine atoms, C * -C ₄ alkoxy or C _] - C ₄ haloalkoxy with 1 to 5 same

25 or different halogen atoms, such as fluorine and

Chlorine atoms

Q particularly preferably stands for one of the groupings

in which

Z ¹ , Z ² and Z 'are the same or different and represent hydrogen, chlorine, bromine, nitro, methyl, ethyl, n- or i-propyl, n-, I-, s- or t-butyl, CH ₂ F, CHF ₂ , CF ₃ , CH ₂ C1, CH ₂ Br, CHCICH, methoxy, ethoxy, methoxymethyl or ethoxymethyl

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

Methoxymethyl, ethoxymethyl, n-propoxymethyl, n-butoxymethyl, methylcarbonyl, methylsulfonyl, each optionally mono- or disubstituted, identically or differently, by fluorine, chlorine, methyl or tnfluoromethyl, phenylcarbonyl or benzyl, or for cyclopropyl

X particularly preferably represents oxygen or sulfur

Y particularly preferably represents one of the groups

-CH ₂ -, -CH (CH ₃ ) -, -CH (C, 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-, -CHC1-,

-CH - fl-> -CH = CH- or -CH ₂ O-

A is particularly preferred (1) for optionally mono- to trisubstituted, identically or differently substituted phenyl, suitable substituents being halogen, nitro, cyano, C, -C ₁₂ alkyl, C, -C _{] 2} haloalkyl having 1 to 5 identical or different Halogen atoms, such as fluorine and chlorine atoms, C * -C ₄ alkoxy, C * -C ₄ haloalkoxy with 1 to 5 identical or different halogen atoms, such as fluorine and chlorine atoms, C, -C ₄ alkylthio, C, -C ₄ -Halogenalkylthιo with 1 to 5 identical or different halogen atoms, such as fluorine and chlorine atoms, C ₂ -C ₄ alkenyl, C ₂ -C ₄ haloalkenyl with 1 to 5 identical or different halogen atoms, such as fluorine and chlorine atoms, the groupings

W W

- CR - o- -CR ² R ³ - -C - R as well

each optionally one to three times, identical or different, by halogen, nitro, cyano, thiocarbamoyl, C _r C ₄ alkyl, C, -C ₄ - haloalkyl having 1 to 5 identical or different halogen atoms, such as fluorine and chlorine atoms, C * - C ₄ -alkoxy, C * -C, -alkoxy- C, -C ₄ -alkyl, C _] -C ₄ -haloalkoxy with 1 to 5 identical or different halogen atoms, such as fluorine and chlorine atoms, C - C - alkylthio, C _] -C ₄ haloalkylthio with 1 to 5 identical or different halogen atoms, such as fluorine and chlorine atoms, C, -C ₄ -

Alkylthio-C, -C ₄ -alkyl, C, -C ₄ -alkylsulfonyl-C _r C ₄ -alkyl, C _r C ₄ -alkylsulfonyl-C _r C ₄ -alkyl, C, -C ₄ -alkylsulfιnyl, C _r C ₄ -alkylsulfonyl, C _r C ₄ -haloalkylsulfonyl with 1 to 5 identical or different halogen atoms, such as fluorine and chlorine atoms, formyl, C, -C ₄ -alkylcarbonyl, C _r C ₄ -alkoxycarbonyl, Cι- C ₄ -alkoxιmιno-C, -C ₂ alkyl, optionally substituted by C * -C ₂ alkyl substituted Oxadιazol-3-yl or one of the groupings

W w

"1,., I!

-C- R od, er - 0-CR ² R - CR ⁴

substituted phenyloxy, phenylthio, benzyloxy or pyπdyloxy, (2) for cyclopentyl, cyclohexyl, cyclopentenyl or cyclohexenyl which are each mono- to pentasubstituted by identical or different substituents, fluorine, chlorine, bromine, methyl, ethyl, isopropyl, methoxy or trifluoromethyl being suitable as substituents,

(3) for one of the following, optionally single or double, identical to the differently substituted heterocycles:

o ^' I s ^' N

N "^ N -H - I> 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, -

CF ₃ , -CHF ,, -CH ₂ CF ₃ , -CH ₂ -CF, -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 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 R ⁸ for C _r C ₄ alkyl, in particular methyl or ethyl, C _r C ₄ alkyl carbonyl, in particular methyl carbonyl or ethyl carbonyl, and for optionally single or double, identical or different, by C ₁ -C ₄ alkyl, in particular methyl or ethyl, halogen, in particular fluorine or chlorine, C, -C ₄ -haloalkyl, in particular trifluoromethyl, C, -C ₄ -alkoxy, in particular methoxy, and C _r C ₄ -haloalkoxy, in particular trifluoromethoxy-substituted phenylsulfonyl,

or

(4) for the following, arbitrarily linked and optionally mono- to tetrasubstituted, identical or differently substituted bi- or tπcyclic radicals

Adamantyl

where in each case are suitable as substituents

Fluorine, chlorine, bromine, nitro, cyano, methyl, ethyl, methoxy, methylthio,

Trifluoromethyl, trifluoromethoxy or trifluoromethylthio,

in which

R ¹ for hydrogen, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, for optionally up to five times, identically or differently, C ₃ - substituted by fluorine, chlorine, bromine or methyl C ₇ -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, R ² and R ^{3 are} identical or different and represent hydrogen, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl,

R ⁴ for methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, for optionally one to five times (preferably one to three times), the same or different by fluorine, chlorine, bromine or methyl substituted C ₃ -

C ₇ -cycloalkyl or phenyl which is optionally 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-OR ^: 'and = N-NR ⁶ R ⁷ , where

R ^{3 represents} C * -C ₄ alkyl or benzyl which is optionally 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

R and R are the same or different and represent hydrogen, C, -C ₄ alkyl or phenyl which may be monosubstituted to trisubstituted identically or differently, the substituents being 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

Z ¹ and 7? are identical or different and represent 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

very particularly preferably stands for -CH -, -

very particularly preferably represents phenyl which is monosubstituted to trisubstituted by identical or different substituents, substituents being suitable

Fluorine, chlorine, bromine, nitro, cyano, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, n-, I-, s- or t-butoxy, methylthio, CF ₃ , OCF ₃ , OCHF ₂ , SCF ₃ , SCCI ₂ F, CH ₂ Br, CH ₂ C1, the grouping

W

2 3 "4

^• O-CR R— - CR furthermore, if necessary, single to triple, 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-, l-, s- or t-butoxy, methylthio, methylthiomethyl, CF ₃ , OCF, OCHF ₂ , SCF ₃ , SCC1 ₂ F, CH ₂ Br, CH ₂ C1, methoxy carbonyl, Methyl sulfinyl, methylsulfonyl, trifluoromethyl sulfonyl or the group

W ^{1 1} _ p 1 'tion substituted phenoxy,

in which

R ^{1 represents} hydrogen, methyl or ethyl,

R ² and R ^{3 are the} same or different and represent hydrogen or methyl,

R ^{4 represents} methyl or ethyl, and

W stands for oxygen or the grouping = N-OR ¹¹ ,

in which

R ^{5 represents} methyl, ethyl, n- or l-propoyl, n-, 1-, s- or t-butyl or benzyl which is optionally monosubstituted to trisubstituted identically or differently in the ring, fluorine, chlorine, bromine being the 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, Z ¹ and Z ² stand for the abovementioned general, preferred, particularly preferred and very particularly preferred meanings and

X ¹ , X ² , X ³ , X ⁴ and X ⁵ stand for the substituents mentioned above under A in general, preferably, particularly preferably and very particularly preferably for the phenyl or phenoxy radical and

X -1, X _v 2 ", X" ¹ and X can also each represent hydrogen Another preferred group of compounds are those of the formulas (IA) to (ID), in which the phenoxy radical is para to the NR-CO-CH ₂ or NR-CS-CH ₂ group, among these compounds those are particularly preferred in which the substituents X ¹ , X ² , X ³ and X ^{4 are} hydrogen

The general definitions or explanations of residues or explanations given above or in preferred areas apply accordingly to the end products and to the starting and intermediate products

According to the invention, preference is given to the compounds of the formula (I) in which there is a combination of the meanings listed above as preferred (preferred)

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

Meanings exist

According to the invention, particular preference is given to the compounds of the formula (I) in which there is a combination of the meanings listed above as being particularly preferred

In the radical definitions listed above and below, hydrocarbon radicals, such as alkyl or alkenyl - also in connection with heteroatoms such as alkoxy or alkylthio - are in each case straight-chain or branched as far as possible

Examples of the new substituted N-isothιazolyl- (thιo) amιde are listed in Tables 1 to 9

Table 1

X

II

Q-N-C-Y-A (l)

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

R H

X O

Y CH,

A as listed below

Table 2

Table 2 contains compounds of the general formula (I), in which

Y = CH (CH ₃ )

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 (1), 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 = CH ₂

A - - 0 ^ CN

Q = as listed below QQQQ

Table 9

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

A> ° -o NO.

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

Is used in the preparation of compounds of formula (Ia) according to process (a) e.g. Thieno [2,3c] isothiazol-3-yl-amine and [4- (4-cyanophenoxy)] - phenyl-acetic acid chloride as starting materials, the course of the reaction can be represented by the following reaction scheme

If, for example, thieno [2,3c] isothiazol-3-yl- [4- (4-nitrophenoxy)] phenylacetylamine is used 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, the course of the reaction can be represented by the following reaction scheme Lawessons reagent

If one uses in the preparation of compounds of formula (Ib) according to process (c) z B Thιeno [2,3c] ιsothιazol-3-yl-amιn and [4- (4-chlorophenoxy) J-phenyl-dithioacetic acid methyl ester as starting materials, so the reaction sequence can be represented by the following reaction scheme

CH ₃ S-CS-CH ₂ -V _Vθ → _Vci

N "NH"

The aminoisothiazoles of the formula (II) to be used as starting materials in processes (a) and (c) according to the invention are known (cf., for example, GB 1568377, J Chem Res Synop 1989. 29, DE-A 2713573, Can J Chem 1973 (51 ), 1742 or JP 05070469) and / or can be produced by known methods (cf. e.g. the above-mentioned references)

They can also be obtained, for example, by using Aminonitπldeπvate 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 tπethylamine,

and the thioamide derivatives of the formula (VI) thus obtained

in which

Het has the meaning given above,

then oxidatively reacted with an oxidizing agent, such as, for example, H-.O-, bromine or sodium hypochlorite

The Aminonitrildeπvate of formula (V) are known (see, for example, EP-A 0 453 61 1, Acta Chim Scand, Ser B 1975. B 29 (2), 224, DE-A 2713573, Chem Pharm

Bull 1971. 19, 1 19, Tetrahedron Letters, 1989. 30, 263 1, J Chem Soc, Perkins Trans I, 1987. 1521, Helv Chim Acta 1975. 58, 2192, J Med Chem 1987. 30, 91, J Het Chem 1985. 22, 1093 or EP-A 0 636 626) and / or can be prepared by known methods (cf. eg the above-mentioned references)

The acid halides of the formula (III) which are also to be used as starting materials in process (a) according to the invention are generally known compounds of organic chemistry. In the formula (III) shark preferably represents chlorine or bromine

The dithioesters of the formula (IV) which are also to be used as starting materials in process (c) according to the invention are known (cf. for example tetrahedron)

2663 (1984) or J Chem Research (M) 2701 (1988)) and / or can be prepared by known, analogous processes. In formula (IV), Alk preferably represents methyl

Suitable diluents for carrying out process (a) according to the invention are, if appropriate, halogenated aliphatic or aromatic hydrocarbons, ethers or nitols, such as, for example, cyclohexane, toluene, chlorine. benzene, choroform, dichloromethane, dichloroethane, dioxane, tetrahydrofuran, diethyl ether or acetonitrile.

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

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

When carrying out process (a), 1 to 2 mol, preferably 1 to 1.5 mol, of acid halide of the formula (III) are generally employed per mol of aminoisothiazole of the formula (II).

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

Preferred sulfurization agents when carrying out process (b) according to the invention are: phosphorus pentasulfide or Lawesson®

Reagent [2,4-bis (4-methoxyphenyl) -1, 3,2,4-dithiadiphosphetane-2,4-dithione] (see also Tetrahedron Vol. 41, No. 22, 5061 ff (1985)).

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

The reaction temperatures can be varied within a substantial range when carrying out process (b) according to the invention. In general, temperatures between 0 ° C and 200 ° C, preferably between 20 ° C and 150 ° C. When carrying out process (b) according to the invention, between 1 and 3 mol, preferably between 1 and 2 mol, of sulfurizing agent are generally employed per mol of compound of the formula (Ia). Working up is carried out by customary methods

Suitable diluents for carrying out the inventive

Process (c) all customary solvents in question Halogenated aliphatic or aromatic hydrocarbons, such as methylene chloride, dichloroethane, cyclohexane, toluene or chlorobenzene, can preferably be used

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

The reaction temperatures can be carried out when carrying out the inventive

Process (c) can be varied over a wide range. In general, temperatures between 0 ° C and 150 ° C, preferably between 20 ° C and 120 ° C.

When carrying out process (c) according to the invention, 1 to 3 moles, preferably 1 to 1 mole, are generally employed per mole of aminoisothiazole of the formula (II)

1.5 mol of dithioester of the formula (IV) The work-up and isolation is carried out by customary methods

The active ingredients are suitable for good plant tolerance and favorable warm-blood toxicity to control animal pests, especially insects, arachnids and nematodes, which are used in agriculture, in forests, in

Storage and material protection and in the hygiene sector occur. They can preferably be used as plant protection products. They are effective against normally sensitive and resistant species and against all or individual stages of development. The pests mentioned above include

From the order of the Isopoda, e.g. Oniscus asellus, Armadillidium vulgare, Porcellio scaber

From the order of the Diplopoda e.g. Blaniulus guttulatus.

From the order of the Chilopoda e.g. Geophilus carpophagus, Scutigera spec

From the order of the Symphyla e.g. Scutigerella immaculata From the order of the Thysanura e.g. Lepisma saccharina

From the order of the Collembola, for example Onychiurus armatus From the order of the Orthoptera, for example 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, for example, Forficula auricularia. From the order of the Isoptera, for example Reticulitermes spp ..

From the order of the anoplura e.g. Pediculus humanus corporis, Haematopinus spp., Linognathus spp.

From the order of the Mallophaga e.g. Trichodectes spp., Damalinea spp.

From the order of the Thysanoptera e.g. Hercinothrips femoralis, Thrips tabaci. From the order of the Heteroptera e.g. Eurygaster spp., Dysdercus intermedius,

Piesma quadrata, Cimex lectularius, Rhodnius prolixus, Triatoma spp From the order of the Homoptera e.g. Aleurodes brassicae, Bemisia tabaci, Trialeurodes vaporariorum, Aphis gossypii, Brevicoryne brassicae, Cryptomyzus ribis, Aphis fabae, Aphis pomi, Eriosoma lanigerum, Hyalopterus arundinis, Phylloxera vastatrix, Pemphigus sppe, Phrosiphodumonum., Macrosiphodumon. 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 Lepidopter Pectinophora gossypiella, Bupalus piniarius, Cheimatobia brumata, Lithocolletis blancardella, Hyponomeuta padella, Plutella maculipennis, Malacosoma neustria, Euproctis chrysorrhoea, Lymantria spp., Bucculatrix thurberiisisppia, Fpp., Phyllocnist spp., Spodoptera exigua, Mamestra brassicae, Panolis flammea, Spodoptera litura, Spodoptera spp., Trichoplusia ni, Carpocapsa pomonella, Pieris spp., Chilo spp., Pyrausta nubilalis, Ephestia kuehniella, Galleria mellonelliellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaella , Cacoecia podana, Capua reticulana, Choristoneura fumiferana, Clysia ambiguella, Homona magnanima, Tortrix viridana. From the order of the Coleoptera e.g. Anobium punctatum, Rhizopertha dominica, Bruchidius obtectus, Acanthoscelides obtectus, Hylotrupes bajulus, Agelastica alni,

Leptinotarsa decemlineata, Phaedon cochleariae, Diabrotica spp., Psylliodes chrysocephala, Epilachna varivestis, Atomaria spp., Oryzaephilus surinamensis, Anthonomus spp., Sitophilus spp., Otiorrhynchus sulcatordimidhmpphppm, 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 e.g. Diprion spp., Hoplocampa spp., Lasius spp., Monomorium pharaonis, Vespa spp. From the order of the Diptera e.g. 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 e.g. Xenopsylla cheopis, Ceratophyllus spp ..

From the order of the Arachnida e.g. Scorpio maurus, Latrodectus mactans.

From the order of the Acarina e.g. 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., Tarsonaia spp.

Panonychus spp., Tetranychus spp ..

Plant-parasitic nematodes include e.g. Pratylenchus spp., Radopholus 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 notable in particular for outstanding insecticidal activity.

They can be used with particularly good success to control plant-damaging insects. They show strong effects, for example, against horseradish leaf beetle larvae (Phaedon cochleariae), caterpillars of the owl butterfly (Spodoptera frugiperda) and against the green leafhopper (Nephotettix cincticeps).

The active ingredients can be converted into the customary formulations, such as solutions, emulsions, wettable powders, suspensions, powders, dusts, pastes, soluble powders, granules, suspension emulsion concentrates, active ingredient-impregnated natural and synthetic substances and very fine encapsulations in polymers Fabrics. These formulations are prepared in a known manner, for example and preferably by mixing the active ingredients with extenders, that is to say liquid solvents and / or solid carriers, optionally using surface-active agents, that is to say emulsifiers and / or dispersants and / or foaming agents

If water is used as an extender, organic solvents can, for example, also be used as auxiliary solvents. Liquid solvents are essentially aromatics, such as xylene, toluene, or alkylnaphthanes, chlorinated aromatics and chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chlorethylenes or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, for example petroleum fractions, mineral and vegetable oils, alcohols, such as butanol or glycol, and their ethers and esters, ketones such as acetone, methyl ethyl ketone, methylsobutyl ketone or cyclohexanone, strongly polar solvents, such as dimethylformamide and dimethyl sulfoxide, and water

Solid carrier materials are, for example, ammonium salts and natural rock powders, such as kaolins, alumina talc, chalk, quartz, attapulgite, montmole lumps or diatomaceous earth and synthetic rock powders, such as highly disperse silica, aluminum oxide and silicates, and solid carrier materials for granules are possible, for example broken and fractionated natural rocks such as calcite, marble, pumice, sepio th, 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 stalks, as emulsifying and / or foam-generating agents are possible B non-ionic and anionic emulsifiers, such as polyoxyethyl en-

Fatty acid esters, polyoxyethylene fatty alcohol ethers, for example alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates and protein hydrolyzates, and dispersants are, for example, lignin sulfite waste liquors and methyl cellulose

In the formulations, adhesives such as carboxymethyl cellulose, natural and synthetic polymers in the form of powders, granules or latices, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, and also natural phosphides, such as cephalins and lecithins and synthetic phosphophides, can be used. Other additives can be mineral and vegetable oils Dyes such as inorganic pigments, for example iron oxide, titanium oxide, ferrocyan blue and organic dyes such as Ahzaπn, azo and metal phthalocyanine, are used, and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc become

The formulations generally contain between 0.1 and 95% by weight

Active ingredient, preferably between 0.5 and 90%

The active substance according to the invention can, in its commercially available formulations and in the use forms prepared from these formulations, in a mixture with other active substances, such as insecticides, attractants, stonlants, bactericides, acaecides, nematicides, fungicides, regulate growth

Substances or herbicides are present. Insecticides include, for example, phosphoric acid esters, carbamates, carboxylic acid esters, chlorinated hydrocarbons, phenylureas, substances produced by microorganisms and the like

The following are particularly advantageous mixed partners

Fungicides:

2-aminobutane, 2-anion-4-methyl-6-cyclopropyl-pyπmιdιn, 2 ', 6'-dιbromo-2-methy-' -trifluoromethoxy ^ '- tπfluoro-methyl-l, 3-thιazole-5-carboxaneιhd , 2 6-Dι- chloroN- (4-tπfluoromethylbenzyl) -benzamιd, (E) -2-methoxyιmιno-N-methyl-2- (2-phenoxyphenyl) -acetamιd, 8-Hydroxyquιnohnsulfat, methyl- (E) -2- {2- [6- (2-cyano-phenoxy) -pyπmιdιn-4-yloxy] -phenyl} -3-methoxyacrylate, methyl- (E) -methoxιmιno-

[alpha- (o-tolyloxy) -o-tolyl] acetate, 2-phenylphenol (OPP), aldimorph, ampropvlfos, anilazine, azaconazole,

Benalaxyl, Benodanil, Benomyl, Binapacryl, Biphenyl, Bitertanol, Blasticidin-S, Bromuconazole, Bupiπmate, Buthiobate, Calciumpolysulfid, Captafol, Captan, Carbendazim, Carboxin, Chinomethionat

(Quinomethionate), Chloroneb, Chloropicnn, Chlorothalonil, Chlozohnat, Cufraneb, Cymoxanil, Cyproconazole, Cyprofuram,

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

Edifenphos, epoxyconazole, ethirimol, etndiazole,

Fenaπmol, Fenbuconazole, Fenfuram, Fenitropan, Fenpiclonil, Fenpropidin Fen- propimorph, Fentinacetat, Fentinhydroxyd, Ferbam, Feπmzone, Fluazinam, Flu- dioxonil, fluoromide, fluquinconazole, flusilazole, flusulfamide, flutolanil, fluotriafol, folpet, fosetyl aluminum, fthalide, fuberidazole, furalaxyl, furmecyclox,

Guazatine,

Hexachlorobenzene, hexaconazole, hymexazole, imazalil, imibenconazole, iminoctadine, 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, phosdiphene, phthalide, pimaricin, piperalin,

Polycarbamate, polyoxin, probenazole, prochloraz, procymidon, propamocarb, propiconazole, propineb, pyrazophos, pyrifenox, pyrimethanil, pyroquilone,

Quintozen (PCNB),

Sulfur and sulfur preparations,

Tebuconazole, tecloftalam, tecnazen, tetraconazole, thiabendazole, thicyofen,

Thiophanate-methyl, thiram, tolclophos-methyl, tolylfluanid, triadimefon, triadimenol, triazoxide, trichlamide, tricyclazole, tridemorph, triflumizole, triforin,

Triticonazole,

Validamycin A, vinclozolin,

Zineb, ziram.

Bactericides: bronopol, dichlorophene, nitrapyrin, nickel-dimethyldithiocarbamate, kasugamycin, octhilinone, furan carboxylic acid, oxytetracycline, probenazole, streptomycin, tecloftalam, copper sulfate and other copper preparations

Insecticides / acaricides / nematicides:

Abamectin, AC 303 630, acephate, 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, Butocarboxin, Butylpyridaben, Cadusafos, Carbaryl, Carbofuran, Carbophenothion, Carbosulfan, Cartap, CGA 157 419, CGA 184699, Chloethocarb, Chlorethoxyfos, Chlorfenvinphos, Chlorofluazuron, Chlormephos, Chlorpyrifos, Chlorpyrifos M, Cis-Resmethrin, Clocyentoshrinhrin, Cloferthrin, Cloferthrin, Cyan Cyfluthrin, 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, Ethifenin, Ethifenin, Ethifenin, Methamino, Emamofen, Emfom, Oxametheno Ethoprophos, etrimphos,

Fenamiphos, Fenazaquin, Fenbutatinoxid, Fenitrothion, Fenobucarb, Fenothiocarb, Fenoxycarb, Fenpropathrin, Fenpyrad, Fenpyroximat, Fenthion, Fenvalerate, Fipronil, Fluazinam, Flucycloxuron, Flucythrinat, Flufenoxuron, Flufenothionx, Fhrionophon, 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, Fufon, Fufion, Fufion, Fufion, Fufion, Fufox, Fufox 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, Pyrachlophos,

Pyradaphenthion, Pyresmethrin, Pyrethrum, Pyridaben, Pyrimidifen, Pyriproxifen, Quinalphos, RH 5992, Salithion, Sebufos, Silafluofen, Sulfotep, Sulprofos, Tebufenozid, Tebufenpyrad, Tebupirimphos, Teflubenzuron, Tefluthrin

Terbam, Terbufos, Tetrachlorvinphos, Thiafenox, Thiodicarb, Thiofanox, Thiomethon, Thionazin, Thuringiensin, Tralomethrin, Triarathen, Triazophos, Triazuron, Trichlorfon, Triflumuron, Trimethacarb, Vamidloth2, 5Methrin, 5MC, XMC5, 5M1, XMC, 5M3, 5M1

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 present in their commercially available formulations and in the use forms prepared from these formulations in a mixture with synergists. Synergists are compounds that increase the effectiveness of the active ingredients without the added synergist itself having to be active

The active substance content of the use forms prepared from the commercially available formulations can vary within wide ranges. The active substance concentration of the use forms can be from 0.0000001 to 95% by weight of active substance, 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 active ingredient is characterized by an excellent residual effect on wood and clay as well as a 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, rough 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 e.g. Haematopinus spp, Linognathus spp,

Pediculus spp., Phtirus spp., Solenopotes spp

From the order of the Mallophagida and the subordinates Amblyceπna and Ischnocerina e.g. Trimenopon spp, Menopon spp, Trinoton spp, Bovicola spp, Werneckiella spp., Lepikentron spp, Damalina spp, Trichodectes spp, Fe cola spp.

From the order Diptera and the subordinates Nematocerina and Brachycerina, for example Aedes spp., Anopheles spp., Culex spp., Simulium spp, Eusimulium spp., Phlebotomus spp., Lutzomyia spp, Culicoides spp., Chrysops spp., Hybomitraus spp., Atylotan spp., Atylotan 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 Siphonapteπda eg Pulex spp, Ctenocephahdes spp, Xenopsylla spp, Ceratophyllus spp

From the order of the Heteropteπda, for example Cimex spp, Tπatoma spp, Rhodnius spp, Panstrongylus spp

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

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

Mesostigmata e.g. Argas spp, Ornithodorus spp, Otobius spp, Ixodes spp, Amblyomma spp, Boophilus spp, Dermacentor spp, Haemophysahs spp, Hyalomma spp, Rhipicephalus spp, Dermanyssus spp, Rail etia spp, Sternonyssoma spp, Sternonyssoma spp

From the order of the Actinedida (Prostigmata) and Acaπdida (Astigmata) z

Acarapis spp, Cheyletiella spp, Ornithocheyletia spp, Myobia spp, Psorergates spp, Demodex spp, Trombicula spp, Listrophorus spp, Acarus spp, l yrophagus spp, Caloglyphus spp, Hypodectes spp, Ptero chus spp, Choroptes spp, Psoroptes spp, Psoroptes spp, Psoroptes 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 which are agricultural animals such as, for example, cattle, sheep, goats, horses, pigs, donkeys, camels, buffalo, rabbits, chickens, turkeys, ducks, geese, bees , other pets such as dogs, cats, house bird, aquarium fish and so-called experimental animals such as hamsters,

Attacking guinea pigs, rats and mice By combating these arthropods, deaths and reduced performance (in meat, milk, wool, skin, eggs, honey, etc.) are to be reduced, so that the use of the active compounds according to the invention enables more economical and simple animal husbandry is The active compounds according to the invention are used in the veterinary sector in a known manner by enteral administration in the form of, for example, tablets, capsules, drinkers, drenches, granules, pastes, boluses, the feed-through method, suppositories, by parenteral administration, for example by Injections (intramuscular, subcutaneous, intravenous, intraperitoneal, etc.),

Implants, by nasal application, by dermal application in the form of, for example, diving or bathing (dipping), spraying (spray), pouring on (pour-on and spot-on), washing, powdering and with the help of shaped bodies containing active ingredients, such as collars , Ear tags, tail tags, ghedma bands, holsters, marking devices, etc

When used for cattle, poultry, pets, etc., the active compounds of the formula (I) can be formulated (for example powders, emulsions, flowable agents) which contain the active compounds in an amount of 1 to 80% by weight, directly or after 100 Apply up to 10,000-fold dilution or use it as a chemical bath

It has also been found that the compounds of the formula (I) according to the invention have a high insecticidal action against insects which destroy industrial materials

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

Beetle like

Hylotrupes bajulus, Chlorophorus pilosis, Anobium punctatum, Xestobium rufovillosum, Ptilinus pecticornis, Dendrobium pertinex, Ernobius mollis, Pπobium carpini, Lyctus brunneus, Lyctus africanus, Lyctus planicollis, Lyctus linusoxesxes, speculum, Lyctus linusoxes, specie

Tryptodendron spec Apate monachus, Bostrychus capucins, Heterobostrychus brunneus, Sinoxylon spec. Dinoderus minutus

Hautflieger like

Sirex juvencus, Urocerus gigas, Urocerus gigas taignus, Urocerus augur Termites like

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

Bristle tails like Lepisma saccarina.

In the present context, technical materials are to be understood as non-living materials, such as preferably plastics, adhesives, glues, papers and cartons, leather, wood and wood processing products and paints

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

Wood and wood processing products which can be protected by the agent according to the invention or mixtures containing it are to be understood as examples: timber, wooden beams, railway sleepers, bridge parts, jetties, wooden vehicles, boxes, pallets, containers, telephone masts, wooden cladding,

Wooden windows and doors, plywood, chipboard, carpentry or wood products that are used in general in house construction or joinery

The active substances can be used as such, in the form of concentrates or generally customary formulations such as powders, granules, solutions, suspensions, emulsions or pastes.

The formulations mentioned can be prepared in a manner known per se, e.g. by mixing the active ingredients with at least one solvent or diluent, emulsifier, dispersant and / or binder or fixative, water repellent, optionally siccatives and UV stabilizers and optionally dyes and pigments and further processing aids

The insecticidal compositions or concentrates used to protect wood and wood-based materials contain the active compound according to the invention in a concentration of 0.0001 to 95% by weight, in particular 0.001 to 60% by weight. The amount of the agents or concentrates used depends on the type and the occurrence of the insects and on the medium. The optimum amount can be determined in each case by use of test series. In general, however, it is sufficient from 0.0001 to 20% by weight, preferably 0.001 to 10 wt .-% of the active ingredient, based on the material to be protected

An organic-chemical solvent or solvent mixture and / or an oily or oil-like difficultly volatile organic-chemical solvent or solvent mixture and / or a polar organic-chemical solvent or solvent mixture and / or water and optionally an emulsifier and / or wetting agents

The organic chemical solvents used are preferably oily or ol-like solvents with an evaporation number above 35 and a flash point above 30 ° C., preferably above 45 ° C. Corresponding mineral oils or their aromatic fractions or mineral oil-containing solvent mixtures, preferably white spirit, petroleum and / or alkylbenzene, are used as such slightly volatile, water-insoluble, oily and oil-like solvents

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

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

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

According to a preferred embodiment, part of the organic chemical solvent or solvent mixture is replaced by an aliphatic polar organic chemical solvent or solvent mixture. Aliphatic organic chemical solvents containing hydroxyl and / or ester and / or ether groups, such as, for example, glycol ethers, are preferred. Ester or the like for use

In the context of the present invention, the known organic-chemical binders are synthetic resins which are known to be water-thinnable and / or soluble or dispersible or dispersible or emulsifiable in the organic-chemical solvents used, and / or binding drying oils, in particular binders consisting of or containing an acrylic resin, a vinyl resin, for example 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 synthetic resin are used

The synthetic resin used as a binder can be used in the form of an emulsion, dispersion or solution. Bitumen or bituminous substances of up to 10% by weight can also be used as binders. In addition, known dyes, pigments, water-repellent agents, odorants tien and inhibitors or corrosion protection agents and the like are used

According to the invention, at least one alkyd resin or modified alkyd resin and / or a drying vegetable oil is preferably contained in the agent or in the concentrate as the organic chemical binder. According to the invention, alkyd resins with an oil content of more than 45% by weight, preferably 50, are preferred up to 68% by weight.

All or part of the binder mentioned can be replaced by a fixing agent (mixture) or a plasticizer (mixture). These additives are intended to volatilize the active ingredients and to crystallize or prevent falling 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 tπbutyl phosphate, adipic acid esters such as di- (2-ethylhexyl) adipate, stearates such as butyl stearate or amyl stearate, oleatolecies such as butyl oleate or glycerol - Kolether, glycerol ester and p-toluenesulfonic acid ester

Fixing agents are chemically based on polyvinyl alkyl ethers such as polyvinyl methyl ether or ketones such as benzophenone and ethyl enbenzophenone

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

A particularly effective wood protection is achieved by large-scale impregnation processes, eg vacuum, double vacuum or printing processes

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

Possible additional admixing partners are preferably the insecticides and fungicides mentioned in WO 94/29 268. The compounds mentioned in this document are an express component of the present application

Insecticides, such as chlorpyphos, phoxim, silafluofin, alphamethrin, cypermethrin, deltamethin, permethrin, imidacloprid, hexaflumuron, triflizolez, as well as fazonazole, are as very particularly preferred Tebuconazole, cyproconazole, metconazole, imazalil, dichlorfluanid, tolylfluanid,

3-iodo-2-propinyI-butyl carbamate, N-octyl-isothiazolin-3-one and 4,5-Dιchlor-N-oc-tylisothiazolin-3-one called

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

example 1

(Method a)

To a solution of 1.60 g (0.01 mol) of Thιeno [2,3c] ιsothιazol-3-yl-amine in 15 ml of pyπmidine and 50 ml of acetonitrile, a solution of 3.50 g (0.012 mol) of 4- (4- Nιtrophenoxy)] - phenylessιgsaurechloπd added dropwise in 20 ml of acetonitrile. The mixture is stirred at 25 ° C. for 18 hours and then evaporated to dryness. The reaction mixture is taken up in water / ethyl acetate and the organic phase is washed several times with 10% strength sodium hydroxide solution and concentration gives a viscous residue which is purified by chromatography on silica gel with methylene chloride / ethyl acetate (20 l) as the eluent

0.24 g (20% of theory) of theno [2.3c] isothιazol-3-yl- [4- (4-mtrophenoxy)] phenylacetylamine of melting point 223 ° C. is obtained

The following compounds of the formula (I) are obtained analogously or according to the general information on the preparation

X

Q -NC -YA (I) IR

Fp (° C) or 1HNMR, δ ppm in d ⁶ -DMSO) Examples of use

Example A

Phaedon larval test

Solvent 7 parts by weight diniethylformamide emulsifier 1 part by weight 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 treated by being dipped into the preparation of active compound of the desired concentration and populated with horseradish leaf beetle larvae (Phaedon cochleariae) while the leaves are still moist

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

In this test, for example, the compound according to Preparation Example 2, with an exemplary active ingredient concentration of 0.1%, caused 100% death after 7 days

Example B

Spodoptera Frugiperda test

Solvent 7 parts by weight of dimethylformamide

Emulsifier 1 part by weight of alkylaryl polyglycol ether

Cabbage leaves (Brassica oleracea) are treated by being dipped into the preparation of active compound of the desired concentration and with caterpillars of the owl butterfly

(Spodoptera frugiperda) occupied while the leaves are still moist

After the desired time, the death rate is determined in%. 100% means that all the caterpillars have been killed, 0% means that none of the caterpillars have been killed

In this test, for example, the compound according to preparation example 2, with an exemplary active compound concentrate of 0.1%, caused a death rate of 100% after 7 days

Example C

Nephotettix test

Solvent 7 weight unit dimethylformamide

Emulsifier 1 part by weight of alkylaryl polyglycol ether

Rice seedlings (Oryza sativa) are treated with T in the active ingredient preparation of the desired concentration and with larvae of the green rice leafhopper

(Nephotettix cincticeps) occupied while the seedlings are still moist

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

In this test, for example, the compound according to Preparation Example 2, with an exemplary active compound concentration of 0.1%, caused a death rate of 100% after 6 days

Claims

Patent claims

1. Compounds of formula (I)

X

Q-N-C— Y-A ( l ) i

R

in which

Q stands for the grouping.

where

Het represents an optionally substituted heterocycle,

R for hydrogen, alkyl, haloalkyl, alkoxyalkyl, alkylcarbonyl,

Alkylsulfonyl, in each case optionally substituted arylcarbonyl, arylsulfonyl or arylalkyl or optionally substituted cycloalkyl,

X stands for oxygen or sulfur,

Y represents optionally substituted alkylene, alkenylene, alkylenoxy or alkylenethio and

represents optionally substituted aryl, optionally substituted cycloalkyl, optionally substituted cycloalkenyl or an optionally substituted heterocycle

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

Q stands for the grouping,

where

Het represents an optionally mono- to tri-substituted, identically or differently substituted 5- or 6-membered heterocycle with 1 or 2 heteroatoms, such as N, S and O atoms, where as substituents

Halogen, C,-C ₄ -alkyl, C,-C ₄ -alkoxy, C,-C ₄ -haloalkyI with 1 to 5 identical or different halogen atoms, such as

Fluorine, chlorine and bromine atoms, C*-C ₄ -alkoxy-C, -C ₄ -alkyl, nitro, C*-C ₄ -alkylsulfonyl, C*-C ₄ -haloalkylsulfonyl with

1 to 5 identical or different halogen atoms, such as fluorine and chlorine atoms as well as thiocarbamoyl, come into question,

R for hydrogen, C*-C ₄ alkyl, C,-C ₄ haloalkyl with 1 to 5 identical or different halogen atoms, such as fluorine and chlorine atoms, C ₁ -C ₄ alkoxy-C _] -C ₄ alkyl, C*-C ₄ -alkyl-carbonyl, C*-C ₄ -alkylsulfonyl, in each case optionally mono- to tri-substituted, identically or differently substituted in the phenyl carbonyl, phenyl sulfonyl or benzyl, the substituents being halogen, nitro, cyano, C* -

C ₄ alkyl, C*-C ₂ haloalkyl with 1 to 5 identical or different halogen atoms, such as fluorine and chlorine atoms, C*-C ₄ alkoxy, C--C ₄ alkylthιo, C.-C ₂ haloalkoxy with 1 to 5 identical or different halogen atoms, such as fluorine and chorine atoms or C*-C,-haloalkylthιo with 1 to 5 identical or different halogen atoms, such as fluorine and chlorine atoms, or for optionally single to triple, identical or different is C ₃ -C ₆ cycloalkyl substituted by C,-C ₄ -alkyl or halogen,

X stands for oxygen or sulfur, Y for C _r C ₆ -alkylene, C,-C ₆ -hydroxyalkylene, C,-C ₄ -alkoxy-C _r C ₆ -alkylene, C _r C ₄ -alkylcarbonyloxy-C.-C ₆ -alkylene, cyano -C _r C ₆ -alkylene, C,-C ₄ -haloalkylene with 1 to 5 identical or different

halogen atoms such as fluorine and chlorine atoms; optionally single to triple, identical or different from fluorine, chlorine or

Methyl substituted C ₃ -C ₆ -cycloalkyl-C _] -C ₄ -alkylene, C ₂ -C ₄ -alkenylene, C^C^alkyleneoxy or C*-C ₄ -alkylenethio,

A (1) represents phenyl which is optionally mono- to tri-substituted, identically or differently substituted, suitable substituents being:

Halogen, nitro, cyano, C* -C ₁₂ -alkyl, C.-C _p -haloalkyl with 1 to 5 identical or different halogen atoms, such as fluorine and chlorine atoms, C.-C _]2 -alkoxy, C _r C ₁₂ - Halogenalkoxy with 1 to 5 identical or different halogen atoms, such as fluorine and chlorine atoms, C,-C _I2 -alkylthio, C.-C _p -halogenalkylthio with 1 to 5 identical or different halogen atoms, such as fluorine and chlorine atoms, C ₂ -C ₁₂ -alkenyl, C,-C* ₂ -haloalkenyl with 1 to 5 identical or different halogen atoms, such as fluorine and chlorine atoms, optionally single to triple, identical or different

C _j - _j -alkyl or halogen substituted C^-C ₈ -cycloalkyl, the groups

W W

— CR — 0-CR ² R — CR as well

each optionally single to triple, the same or different through halogen, nitro, cyano, thiocarbamoyl, C <-

C ₄ alkyl, C,-C ₄ haloalkyl with 1 to 5 identical or different halogen atoms, such as fluorine and chlorine atoms, C _r C ₄ alkoxy, C _r C ₄ alkoxy-C _r C ₄ alkyl, C _r C ₄ -halo-alkoxy with 1 to 5 identical or different halogen atoms, such as fluorine and chlorine atoms, C _] -C ₄ -alkylthio, C _r C ₄ -

Halogenalkylthio with 1 to 5 identical or different halogen atoms, such as fluorine and chlorine atoms, C _r C ₄ -alkylthio-C _r C ₄ -alkyl, C _r C ₄ -alkylsulfιnyl-C _r C ₄ -alkyl, C,-C ₄ -Al- kylsulfonyl-C,-C ₄ -alkyl, C _r C ₄ -alkylsulfιnyl, C,-C ₄ -alkyl-sulfonyl, C * -C ₄ -haloalkyl sulfonyl with 1 to 5 identical or different halogen atoms, such as fluorine and chlorine atoms, Formyl, C,-C ₄ -alkylcarbonyl, C,-C ₄ -alkoxy-carbonyl, C.-C ₄ -alkoximino-C*-C ₄ -alkyl, optionally through

C,-C ₄ -alkyl substituted oxadiazolyl or one of the groups

W W

^{1 1} 1 7 1 II Λ

— C - R , — 0-CR ² R — C- R ⁴ or

substituted phenyl, phenyloxy, phenylthio, benzyl, benzyloxy, pyridyloxy, pyrimidyloxy, pyrazinyloxy or

pyridazinyloxy;

(2) represents C ₃ -C ₈ -cycloalkyl or C ₅ -C _R -cycloalkenyl which is optionally mono- to five-substituted, identically or differently substituted, the substituent being C,-C ₄ -alkyl. C _r C ₄ haloalkyl with 1 to 5 identical or different

Halogen atoms, such as fluorine and chlorine atoms, C _j -C ₄ -alkoxy, C -C -haloalkoxy with 1 to 5 identical or different halogen atoms, such as fluorine and chlorine atoms, C ^ -C ₈ -cycloalkyl, and optionally single to triple , identical or different due to halogen, cyano, nitro, C*-C ₄ -alkyi,

C*-C ₄ -haloalkyl with 1 to 5 identical or different halogen atoms, such as fluorine and chlorine atoms, C _r C ₄ -alkoxy, or C _] -C ₄ -haloalkoxy with 1 to 5 identical or different halogen atoms, such as fluorine and Chlorine atoms substituted phenyl come into question;

(3) represents a 5- or 6-membered heterocycle with 1 to 3 heteroatoms, such as N, S and O atoms, which is optionally mono- to tri-substituted, identically or differently substituted, and which optionally also contains one or more CO or CS Can contain groups as ring members, with possible substituents being: Halogen, nitro, cyano, C,-C ₄ -alkyl, C,-C ₄ -alkoxy, C,-C ₄ -alkylthio, C,-C ₄ -haloalkyl with 1 to 5 identical or different halogen atoms, such as fluorine and Chlorine atoms, C*-C ₄ -haloalkoxy with 1 to 5 identical or different halogen atoms, such as fluorine and chlorine atoms, C,-C ₄ -halo-alkylthio with 1 to 5 identical or different halogen atoms, such as fluorine and chlorine atoms, or in each case optionally phenyl, phenoxy, phenylthio or benzyl substituted once to three times, identically or differently, which can be used as substituents

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

Halogenalkylthio 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 is substituted instead of the hydrogen atom by C* -C ₆ -alkyl, C, -C ₆ -alkylcarbonyl or phenyl sulfonyl can be, which in turn is optionally replaced by Cχ-C _β -alkyl, halogen, C.-C ₄ -haloalkyl with 1 to 5 identical or different halogen atoms, such as fluorine or chlorine atoms, C,-C ₄ -alkoxy or C,-C ₄ -Haloalkoxy with 1 to 5 identical or different halogen atoms, such as fluorine or

chlorine atoms, is substituted,

or

(4) represents fused bi- or tπcyclic radicals which are optionally mono- to five-substituted, identically or differently substituted and which may also contain one or more heteroatoms, such as O, S or N atoms or one or more CO groups as ring members, whereby possible substituents are

Halogen, nitro, cyano, C,-C ₄ alkyl, CC^haloalkyl with 1 to 5 identical or different halogen atoms, such as Fluorine and chlorine atoms, C,-C ₄ -alkoxy-C,-C ₄ -alkyl, C,-C ₄ -alkoxy, C _j -C ₄ -haloalkoxy with 1 to 5 identical or different halogen atoms, such as fluorine and chlorine atoms , C,-C ₄ -AlkyIthio, C,-C ₄ -haloalkylthio with 1 to 5 identical or different halogen atoms, such as fluorine and chlorine atoms, C*-C ₄ -alkylsulfιnyl, C*-C ₄ -alkylsulfonyl, hydroxy, Mercapto, C--C ₄ -alkylcarbonyl, C*-C ₄ -haloalkyl-carbonyl with 1 to 5 identical or different halogen atoms, such as fluorine and chlorine atoms, C,-C ₄ -alkoxy-carbonyl or each

10 because optionally mono- to tri-substituted, identical or different, especially in the phenyl part, phenyl, phenoxy, phenylthio or benzyl, suitable substituents being halogen, nitro, cyano, C* _-C4 -alkyl, _Cj -C^Alkoxy, C* _-C4 -

15 alkylthio, C _j -C ₄ -HalogenaIkyl with 1 to 5 identical or different halogen atoms, such as fluorine and chlorine atoms, C,- C ₄ -haloalkoxy with 1 to 5 identical or different halogen atoms, such as fluorine and chlorine atoms and C _| -C ₄ - haloalkylthio with 1 to 5 identical or different

20 halogen atoms, such as fluorine and chlorine atoms,

where

R ¹ for hydrogen, C, -C ₈ -alkyl, C, -C ₄ -haloalkyl with 1 to 5 identical or different halogen atoms, such as fluorine and chlorine atoms, for optional

25 single or multiple, the same or different

Halogen or C ₁ -C ₄ -alkyl substituted C ₃ -C ₇ - cycloalkyl or optionally mono- to tri-substituted, identically or differently substituted phenyl, with halogen, C, -C ₄ -alkyl as substituents

30 or C.- _C.sub.4 alkoxy come into question,

R ² and R ³ are the same or different and represent hydrogen or C--C ₄ alkyl; R ⁴ for C,-C ₈ alkyl, C _r C ₄ haloalkyl with 1 to 5 identical or different halogen atoms, such as

Fluorine and chlorine atoms, for optionally single or multiple, identical or different through halo-

5 gen or C,-C ₄ -alkyl is substituted C -C ₇ -cycloalkyl or is optionally mono- to tri-substituted, identically or differently substituted phenyl, with halogen, C * -C ₄ -alkyl or C xC _A -alkoxy as substituents question come, and

10 W represents oxygen or one of the groups ^N-OR ³ and =N-NR ⁶ R ⁷ , where

R ³ for C _] -C -alkyl or for optionally single to triple, identical or different from halogen, nitro, cyano, thiocarbamoyl,

15 C _r C ₄ -alkyl, C,-C -haloalkyl with 1 to 5 identical or different halogen atoms, such as fluorine and chlorine atoms, C.-C ₄ -Al oxy, C.-C ₄ -alkoxy-C*-C ₄ -alkyl, C*-C ₄ -haloalkoxy with 1 to 5 identical or different

20 halogen atoms, such as fluorine and chlorine atoms,

C*-C ₄ -alkylthιo, C,-C ₄ -haloalkylthιo with 1 to 5 identical or different halogen atoms, such as fluorine and chlorine atoms, C^ -C^ alkylthιo-C,-C ₄ -alkyl, C _] -C ₄ -Alkylsulfιnyl-

25 C _r C ₄ -alkyl, C _r C ₄ -alkylsulfonyl-C _r C -alkyl,

C*-C ₄ -alkyl sulfinyl, C*-C ₄ -alkylsulfoπyl C, - C ₄ -haloalkylsulfonyl with 1 to 5 identical or different halogen atoms, such as fluorine and chlorine atoms, formyl, C _] -C ₄ -alkyl-

30 carbonyl, C _j -C ₄ -alkoxy-carbonyl or C*-C ₄ -

Alkoximino-C,-C ₄ -alkyl substituted benzyl stands, and

R and R are the same or different and are hydrogen, C,-C ₆ -alkyl or optionally single to three times, identically or differently substituted phenyl, suitable substituents being halogen, nitro, cyano, C _] -C ₄ -alkyl, C * -C ₄ -haloalkyl with 1 to 5 identical or different halogen atoms, such as fluorine and chlorine atoms, C*-C ₄ -alkoxy or C _] -C ₄ -haloalkoxy with 1 to 5 identical or different halogen atoms, such as fluorine and chlorine atoms

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

Q for one of the groups

stands, whereby

Z ¹ , Z ² and Z ³ are the same or different and represent hydrogen, chlorine, bromine, nitro, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl; CH ₂ F, CHF ₂ , CF ₃ , CH ₂ C1, CH,Br, CHC1CH ₃ , methoxy, ethoxy, methoxymethyl or ethoxymethyl,

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

Ethoxymethyl, n-propoxymethyl, n-butoxymethyl; methylcarbonyl, methylsulfonyl; in each case phenyl carbonyl or benzyl, optionally substituted once or twice, identically or differently by fluorine, chlorine, methyl or trifluoromethyl; or stands for cyclopropyl,

X stands for oxygen or sulfur,

Y for one of the groups

-CH ₂ -, -CH(CH ₃ )-, -CH(C ₂ H _S )-, -CH(nC ₃ H ₇ )-, CH(iC.H ₇ )-, -CH,-CH,-, -CH(OH)-, -CH(OCH ₃ )-, -CH(O-CO-CH,)-, -CH(CN)-,

-CHF-, -CHC1-, -CH -<| , -CH=CH- or -CH,0- stands,

A (1) represents optionally mono- to tri-substituted, identically or differently substituted phenyl, suitable substituents being

Halogen, nitro, cyano, C,-^, -alkyl, C _r C ₁₂ -haloalkyl with 1 to 5 identical or different halogen atoms, such as fluorine and chlorine atoms, C, -C ₄ -alkoxy, C _r C ₄ -haloalkoxy with 1 to 5 identical or different halogen atoms, such as fluorine and chlorine atoms, C _| -C ₄ -alkylthio, C _] -C ₄ -haloalkylthio with 1 to 5 identical or different halogen atoms, such as fluorine and chlorine atoms, C, -C ₄ -Alkenyl, C, -C ₄ - halogenalkenyl with 1 to 5 the same or different

Halogen atoms, such as fluorine and chlorine atoms, form the groups

W W

II 1 ιι

— C - R ¹ , — 0-CR ² R ³ — C-R ⁴ as well

each optionally single to triple, the same or different by halogen, nitro, cyano, thiocarbamoyl, C--

C ₄ alkyl, C,-C ₄ haloalkyl with 1 to 5 identical or different halogen atoms, such as fluorine and chlorine atoms, C,-C ₄ alkoxy, C--C ₄ alkoxy-C.-C ₄ alkyl , C*-C ₄ -haloalkoxy with 1 to 5 identical or different halogen atoms, such as fluorine and chlorine atoms, C*-C -alkylthιo, C,-C ₄ -haloalkylthio with 1 to 5 identical or different halogen atoms, such as fluorine and chlorine atoms, C*-C ₄ -Alkylthιo-C _r C ₄ - alkyl, C _r C ₄ -alkylsulfιnyl-C _r C -alkyl, C,-C ₄ -alkylsulfonyl- C _r C ₄ -alkyl, C _r C ₄ -alkylsulfιnyl, C,-C ₄ - Alkyl sulfonyl, C,- C ₄ -haloalkylsulfonyl with 1 to 5 identical or different halogen atoms, such as fluorine and chlorine atoms, formyl, C,-C ₄ -alkylcarbonyl, C ₁ -C ₄ -alkoxy-carbonyl, C,- C ₄ -alkoxy-ιmιno-C,-C,-alkyl, oxadιazol-3-yl optionally substituted by C -C _^ -alkyl or one of the groups

W W

^M 1 , , ιι

— C-R . — 0-CR ² R — CR ⁴ or substituted phenyloxy, phenylthio, benzyloxy or pyridyloxy,

(2) represents cyclopentyl, cyclohexyl, cyclopentenyl or cyclohexenyl which are optionally substituted once to five times, identically or differently, with suitable substituents being fluorine, chlorine, bromine, methyl, ethyl, isopropyl, methoxy or trifluoromethyl,

(3) represents one of the following, optionally once or twice, the same as the differently substituted heterocycles

f S , * TB NTN

N ^" ^N

— μ — I 'where each can be used as a substituent

Fluorine, chlorine, nitro, cyano, methyl, ethyl, n- or i-propyl n-, 1-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxv, methylthio, -CF„ -CFIF, , -CH,CF , -CH,-CF,-CHF,,

-CH(CF )-CH , -OCF„ -OCHF,, -OCH,CF ₃ , -O-CH,-CF ₂ -CF.-, -OCH,-CF,-CHF,, -O-CH(CF ₃ )-CH,, -SCF" and optionally mono- or disubstituted, identically or differently substituted phenyl, phenoxy or phenylthio, suitable substituents being fluorine, chlorine, nitro, cyano, methyl, ethyl, methoxy, ethoxy, Methylthio, trifluoromethyl, Tnfluoromethoxy or Tπfluoromethylthio,

and where

R ⁸ is C _r C ₄ alkyl, especially methyl or ethyl, C _r

C ₄ - alkyl carbonyl, especially methylcarbonyl or

Ethyl carbonyl, and for optionally single or double, identical or different, C*-C ₄ alkyl, in particular methyl or ethyl, halogen, in particular whose fluorine or chlorine, C.- _C.sub.4 -haloalkyl, in particular Tnfluoromethyl, C.sub.- _C.sub.4 -alkoxy, in particular methoxy, and C* _-C.sub.4 -haloalkoxy, in particular Tπfluoromethoxy substituted phenyl sulfonyl,

or

(4) stands for the following, arbitrarily linked and optionally mono- to four-fold, identically or differently substituted bi- or tπcych radicals

0 ^Adaman,vι '

each of which can be used as a substituent

Fluorine, Chlorine, Bromine, Nitro, Cyano, Methyl, Ethyl, Methoxy,

Methylthio, Tnfluoromethyl, Tπfluoromethoxy or Tπfluoromethylthio,

where

R ¹ represents hydrogen, methyl, ethyl, n- or i-propyl, n-, I-, s- or t-butyl, for C - C which is optionally mono to five times, identically or differently substituted by fluorine, chlorine, bromine or methyl ₇ -Cycloalkyl or is optionally mono- to tri-substituted, identically or differently substituted phenyl, suitable substituents being fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, methoxy or ethoxy,

R ² and R ³ are the same or different and represent hydrogen, methyl, ethyl, n- or i-propyl, n-, ι-, s- or t-butyl, R ⁴ for methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, for optionally one to five times (preferably one to three times), the same or different from fluorine, chlorine, bromine or methyl substituted C ₃ -C ₇ cycloalkyl or optionally mono- to tri-substituted, identically or differently substituted phenyl, suitable substituents being fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, methoxy or ethoxy; and

w represents oxygen or one of the groups ^N-OR ³ and =N-NR ⁶ R ⁷ , where

R ^*1 represents C,-C ₄ -alkyl or benzyl which is optionally mono- to tri-substituted, identically or differently substituted, suitable substituents being

Fluorine, chlorine, bromine, cyano, nitro, trifluoromethyl, trifluoromethoxy, methylthio, methyl sulfinyl, methylsulfonyl, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy or ethoxy ; and

R ⁶ and R ⁷ are the same or different and represent hydrogen, C ₁ -C alkyl or optionally mono- to tri-substituted, identically or differently substituted phenyl, whereby as substituents

Fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, trifluoromethyl, methoxy or fluoromethoxy come into question

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

for one of the groups

stands, where

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

R represents hydrogen, methyl, ethyl, methoxymethyl, ethoxymethyl, methylcarbonyl, phenylcarbonyl or methylsulfonyl,

X stands for oxygen or sulfur,

Y stands for -CH,-,

A represents phenyl which is optionally mono- to tri-substituted, identically or differently substituted, suitable substituents being

Fluorine, chlorine bromine, nitro, cyano, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl; Methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methylthio, CF ₃ , OCF ₃ , OCHF,, SCF ₃ , SCC1,F, CH,Br, CH,C1, the grouping W CR 2 R 3- C "- 4

, furthermore, if necessary, single to triple,

the same or different due to 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, CF ₃ , OCF ₃ , OCHF,, SCF ₃ , SCC1,F, CH,Br, CH,C1, Methoxy carbonyl, Methylsulfinyl, Methylsulfonyl,

W

^{1 1} 1 Trifluoromethylsulfonyl or the group — C ^~ R

substituted phenoxy,

where

R ¹ represents hydrogen, methyl or ethyl; R ² and R ³ are the same or different and represent hydrogen or methyl,

R ⁴ represents methyl or ethyl, and

W stands for oxygen or the group =N-OR ⁵ ,

where

R ⁵ for methyl, ethyl, n- or l-propyl, n-, i-, s- or t-

Butyl or benzyl which is optionally substituted once to three times, identically or differently in the ring, the substituents being fluorine, chlorine, bromine, nitro, cyano, methyl, ethyl, methoxy or ethoxy

question come

Process for the preparation of compounds of formula (I) according to claim 1, characterized in that

a) the new substituted N-isothiazolyl amides of the formula (Ia)

O _Q _ _N _ _c II _ _γ _ _A ( ia ) i R

in which

Q, R, Y and A have the meaning given above,

obtained when aminoisothiazoles of the formula (II)

Q-N-H ( II ) i R

in which

Q and R have the meaning given above, with acid halides of the formula (III)

Hal-CO-Y-A (III)

in which

Y and A have the meaning given above and

Hai stands for halogen,

reacted 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)

Q-N-C -Y-A ( Ib ) i R in which

Q, R, Y and A have the meaning given above,

is obtained if the N-isothiazolylamides of the formula (Ia) obtainable according to process (a) are obtained

Q-N-C — Y-A ( Ia ) i

R

in which

Q, R, Y and A have the meaning given above,

reacted with a sulfur agent, optionally in the presence of a diluent, or

c) the new substituted N-isothiazolyl-thioamides of the formula (Ib)

S

II

Q-N-C — Y-A ( Ib )

IR

in which

Q, R, Y and A have the meaning given above,

obtained when aminoisothiazoles of the formula (II)

Q-N-H ( II ) i

R

in which

Q and R have the meaning given above,

with dithioesters of the formula (IV)

S

II

Alk S-C-Y-A (IV)

in which

Y and A have the meaning given above and

Alk represents alkyl or the group MO-CO-CH ₂ -, where M represents an alkali metal (such as sodium or potassium),

optionally implemented in the presence of a diluent

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

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

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

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