WO1999000375A1 - Substituted aminoheterocyclylamides - Google Patents

Abstract

New substituted aminoheterocyclylamides have the formula (I), in which Het stands for one of the heterocycles (a), (b), (c) or (d) and R?1, R2, R3, R4, R5, X1, X2¿, m and n have the meanings indicated in the description. Also disclosed are processes for preparing the same and their use as pesticides and fungicides.

Description

Substituted aminoheterocvlylamides

The invention relates to new substituted aminoheterocyclylamides, processes and intermediates for their preparation and their use for controlling animal pests and as fungicides.

It is already known that certain N-heterocyclylamides, such as, for example, isothiazolyl, pyridyl, thiadiazolyl or pyrimidinyl amides, have insecticidal properties (cf., for example, WO 95/31 448, DE-A-9 542 372; WO 93/04 580, WHERE

96/08 475, DE-A-4 434 637; WO 97/26 251 and WO 95/18 795).

The effectiveness and range of action of these compounds, however, is not always completely satisfactory, especially at low application rates and concentrations.

New substituted aminoheterocyclylamides of the formula (I) have been found

in which

Het for one of the heterocycles

_^R. or

^{R 'N} -v _Q is where

R ^{1 represents} alkyl, haloalkyl, alkoxyalkyl, alkylthioalkyl, alkoxy, alkylthio or optionally substituted cycloalkyl, R ^{2 represents} hydrogen, halogen, cyano, nitro, thiocyanato, alkoxycarbonyl, alkenyloxycarbonyl, alkylthio, haloalkylthio, alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, haloalkylsulfonyl or thiocarbamoyl or

R ¹ and R ² together with the carbon atoms to which they are attached represent an optionally substituted 5- or 6-membered carbocyclic ring,

R ^{3 represents} hydrogen, alkyl, haloalkyl, alkoxyalkyl, alkylcarbonyl, alkoxycarbonyl, alkenyloxycarbonyl, alkylsulfonyl, in each case optionally substituted arylcarbonyl, aryloxycarbonyl, arylsulfonyl or arylalkyl or optionally substituted cycloalkyl,

R ⁴ and R ⁵ independently of one another for hydrogen or for the radicals -COR ⁶ ,

-COOR ⁷ or -SO R ⁸ , where

R ⁶ , R ⁷ and R ⁸ independently of one another are alkyl, haloalkyl, alkoxyalkyl, alkylthioalkyl, alkylcarbonyloxyalkyl, alkoxycarbonylalkyl; Alkenyl, haloalkenyl; Alkynyl, haloalkynyl; each optionally substituted cycloalkyl, cycloalkylalkyl, cycloalkoxyalkyl or cycloalkylthioalkyl; each optionally substituted aryl, arylalkyl, aryloxyalkyl or arylthioalkyl or represent an optionally substituted heterocycle,

X ¹ and X ² independently of one another represent halogen, nitro, cyano, alkyl, alkoxy or haloalkyl,

m and n independently of one another represent 0, 1, 2 or 3,

Y stands for optionally substituted alkylene, alkenylene or alkyleneoxy, and

Halogen for F, Cl, Br, I, in particular for F, Cl, Br and highlighted for F or Cl.

It has also been found that the substituted aminoheterocyclylamides of the formula (I) are obtained if

a) nitro derivatives of the formula (II)

in which

Het, R ³ , X ¹ , X ² , Y, m and n have the meaning given above,

with base metals in acidic solution or by catalytic hydrogenation, optionally in the presence of a diluent and

b) optionally the amino derivatives of the formula (1-1) thus obtained

in which

Het, R ³ , X ¹ , X ² , Y, m and n have the meaning given above,

with compounds of the formula (III)

in which

R ⁴ " ^{1 stands} for the meanings of R ⁴ , except hydrogen, and

G represents a leaving group, e.g. for halogen (especially chlorine), imidazolyl, benzimidazolyl, 1,2,4-triazolyl, pyrazolyl or benzotriazolyl,

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

or

c) amino heterocycles of the formula (IV)

Het - H

N (IV),

in which

Het and R ^{3 have} the meaning given above,

with compounds of formula (V)

in which G, R ⁴ " ¹ , R ⁵ , X ¹ , X ² , Y, m and n have the meaning given above,

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

Finally, it was found that the new substituted aminoheterocyclylamides of the formula (I) have highly pronounced biological properties and above all as fungicides and for combating animal pests, in particular insects, arachnids and nematodes, which are used in agriculture, in the forests, in the

Storage and material protection as well as in the hygiene sector are suitable

Formula (I) provides a general definition of the substituted aminoheterocyclylamides according to the invention

Preferred substituents or ranges of the radicals listed in the formulas mentioned above and below are explained below

Het preferably represents the heterocycles

R ¹ preferably represents -C-alkyl, C -haloalkyl having 1 to 5 identical or different halogen atoms, such as fluorine, chlorine and bromine atoms, C ₁ -C ₄ -alkoxy-C ₁ -C -alkyl, Cι-C ₄ -Alkylthio-C ₁ -C4-alkyl, -C-C ₄ -alkoxy, C ₁ -C ₄ -alkylthio or for optionally single to triple, identically or differently substituted by -CC alkyl or halogen substituted C _ß -Cg Cycloalkyl R ² preferably represents hydrogen, halogen, cyano, nitro, thiocyanato, C _j -C ₄ alkoxy carbonyl, C ₂ -C alkenyloxy carbonyl, C ₁ -C ₄ alkyl thio, C ₁ -C haloalkylthio with 1 to 5 identical or different halogen atoms, such as fluorine or chlorine atoms, -CC ₄ -alkylsulfinyl, -C-C ₄ -haloalkylsulfmyl with 1 to 5 identical or different halogen atoms, such as fluorine or chlorine atoms, C _j -C ₄ - alkylsulfonyl, C ₁ -C ₄ haloalkylsulfonyl having 1 to 5 identical or different halogen atoms, such as fluorine or chlorine atoms or for thiocarbamoyl; or

R ¹ and R ² , together with the carbon atoms to which they are attached, preferably represent a carbocyclic 5- or 6-membered which is optionally monosubstituted to trisubstituted, identically or differently

Ring, suitable substituents being halogen, C ₁ -C4- alkyl, C _j -C ₄ halo-alkyl, C _j -C ₄ - alkoxy, C ₁ -C ₄ -haloalkoxy, nitro and cyano come into question.

preferably represents hydrogen, -CC alkyl, C ₁ -C ₄ haloalkyl having 1 to 5 identical or different halogen atoms, such as fluorine or chlorine atoms, C ₁ -C ₄ alkoxy-C ₁ -C ₄ alkyl, C _r C ₄ alkylcarbonyl, C _r C ₄ alkoxycarbonyl,

C ₂ -C ₄ alkenyloxy-carbonyl, C _! -C ₄ - Alkylsulfonyl, each optionally monosubstituted to trisubstituted, identically or differently, in the phenyl ring, substituted phenylcarbonyl, phenyloxycarbonyl, phenylsulfonyl or benzyl, where in each case halogen, nitro, cyano, C 1 -C ₄ -alkyl, C _] -C ₂ -Halogenalkyl with 1 to 5 identical or different halogen atoms, such as fluorine or chlorine atoms, C _j -C ₄ alkoxy, C ₁ -C4 ~ alkylthio, C _j -C ^ haloalkoxy with 1 to 5 identical or different halogen atoms, such as fluorine or chlorine atoms or C] -C ₂ -haloalkylthio with 1 to 5 identical or different halogen atoms, such as fluorine or chlorine atoms, or, if appropriate, simple to triple, identical or different, by C1-C ₄ -alkyl or

Halogen substituted C ₃ -C ₆ cycloalkyl. R ⁵ independently of one another preferably represent hydrogen or the radicals -COR ⁶ , -COOR ⁷ or -SO ₂ R ⁸ , where

R ⁶ , R ⁷ and R ^8, independently of one another, preferably represent C _j -Cg-alkyl, C _j - Cg-haloalkyl having 1 to 5 identical or different halogen atoms, such as fluorine, chlorine or bromine atoms, -C-C -alkoxy- Cι-C ₈ - alkyl, C ₁ -C ₄ -alkylthio-C ₁ -C ₈ alkyl, C ₁ -C ₄ alkylcarbonyloxy-C ₁ -C ₈ - alkyl, Cι-C alkoxycarbonyl-Cι-C _{4 8} -alkyl; C ₂ -C ₈ alkenyl, C ₂ -C ₈ - haloalkenyl same to 5 with 1 or atoms different halogen such as fluorine or chlorine atoms; C ₂ -C ₈ alkynyl, C ₂ -C ₈ haloalkynyl having 1 to 5 identical or different halogen atoms, such as fluorine or chlorine atoms; for in each case optionally up to five times (preferably once to three times), the same or differently substituted C ₃ -C ₆ cycloalkyl, C ₃ -C ₆ cycloalkyl-C ₄ -C ₄ alkyl, C _ß -Cg-cycloalkyloxy-C _j -

C ₄ -alkyl or C ₃ -C ₆ -cycloalkylthio-C ₁ -C ₄ -alkyl, where each of the substituents is halogen, C _j ^ alkyl, C _j ^ haloalkyl having 1 to 5 identical or different halogen atoms, such as fluorine or chlorine atoms, C _j -C alkoxy, C ₁ -C haloalkoxy with 1 to 5 identical or different halogen atoms, such as fluorine or chlorine atoms, C ₂ -C ₄ -

Alkenyl, C ₂ -C ₄ haloalkenyl with 1 to 5 identical or different halogen atoms, such as fluorine or chlorine atoms, nitro or cyano, are suitable for each optionally substituted up to five times (preferably once to three times), substituted identically or differently in the ring Phenyl,

_{Phenyl-Cι-C4-alkyl,} phenoxy-C ₁ -C ₄ alkyl or phenylthio-C ₁ -C ₄ - alkyl, suitable substituents being in each case halogen, nitro, cyano, C ₄ - alkyl, Cι-C ₄ -Halogenalkyl with 1 to 5 identical or different halogen atoms, such as fluorine or chlorine atoms, C ₁ -C4 alkoxy, C1-C ₄ - haloalkoxy with 1 to 5 identical or different halogen atoms, such as fluorine or chlorine atoms, Cι-C4-alkylthio , C ₁ -C ₄ - haloalkylthio with 1 to 5 identical or different halogen atoms, such as fluorine or chlorine atoms, C ₂ -C ₄ alkenyl, C ₂ -C ₄ - Haloalkenyl with 1 to 5 identical or different halogen atoms, such as fluorine or chlorine atoms,

or C ₁ -C 4 -alkylcarbonyloxy come into question, or for an optionally mono- to trisubstituted, identically or differently substituted 5- or 6-membered heterocycle having 1 to 3 heteroatoms, preferably from the series nitrogen, sulfur and oxygen, the may also contain CO groups as ring members, for example:

, each as a substituent

Halogen, nitro, cyano, C -C - alkyl, Cι-C - alkoxy, C ₁ -C ₄ alkylthio, Cι-C ₄ -Halogena_kyl, C _{j-C4-haloalkoxy} and Cι-C haloalkyl thio in question come. In addition, suitable heterocycles on the ring nitrogen atom can optionally be substituted by a radical Z, where

Z for C _j -C - alkyl (such as in particular methyl or ethyl),

Alkylcarbonyl (such as especially methylcarbonyl or ethylcarbonyl), or for optionally single or double, identical or different by C ₁ -C ₄ alkyl (such as especially methyl or ethyl) halogen (such as especially fluorine or chlorine), C _j - C ₄ Haloalkyl (such as in particular trifluoromethyl), C ₁ -C ₄ - Alkoxy (such as especially methoxy); and C 1 -C ₄ -haloalkoxy (such as in particular trifluoromethoxy) substituted phenylsulfonyl.

Suitable heterocycles are to be understood as meaning nitrogen-containing heterocycles in which at least one ring nitrogen has no double bond and is therefore available for substitution.

X ¹ and X ² independently of one another preferably represent fluorine, chlorine, bromine, nitro, cyano, C ₁ -C ₄ -alkyl, C ₁ -C -alkoxy or C _r C ₄ -haloalkyl having 1 to 5 identical or different halogen atoms, such as Fluorine or chlorine atoms.

m and n independently of one another are preferably 0, 1 or 2.

Y preferably represents C _r C ₆ -alkylene, C _j -C ₆ -hydroxyalkylene, -C-C ₄ -alkoxy-

C Cg-alkylene, C _j -C ^ alkylcarbonyloxy-C Cg-alkylene, cyano-C _j -C ₆ alkyl, C ₁ -C ₄ haloalkylene with 1 to 5 identical or different halogen atoms, such as fluorine or chlorine atoms ; optionally single to triple, identical or different, substituted by fluorine, chlorine or methyl-substituted C ₃ -C6 cycloalkyl -CC-C ₄ alkylene, for C ₂ -C ₄ alkenylene or C ₁ -C ₄ alkyleneoxy.

Halogen preferably represents F, Cl, Br, I, in particular F, Cl, Br and particularly emphasized F and Cl.

Het is particularly preferably one of the heterocycles

R ¹ particularly preferably represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl; CH ₂ C1, CH ₂ Br, CHC1CH ₃ ; Methoxy, ethoxy, methoxy methyl, ethoxymethyl, methylthiomethyl, methylthio or cyclopropyl

R ² particularly preferably represents hydrogen, chlorine, bromine, cyano, nitro, thiocyanato, methoxycarbonyl, ethoxycarbonyl, l-propoxycarbonyl, n-propoxycarbonyl, allyloxycarbonyl, methylthio, methylsulfinyl, methylsulfonyl or CSNH ₂ , or

R ¹ and R ² , particularly preferably together with the carbon atoms to which they are attached, represent an optionally mono- or disubstituted, identically or differently substituted carbocyclic 5- or 6-ghedπgen ring, the substituents being fluorine, chlorine, Methyl, ethyl, methoxy, Tπfluormethoxy, nitro and cyano come into question

R ³ particularly preferably represents hydrogen, methyl, ethyl, n- or l-propyl, methoxymethyl, ethoxymethyl, n-propoxymethyl, n-butoxymethyl, methylcarbonyl, methoxycarbonyl, ethoxycarbonyl, l-propoxycarbonyl, allyloxycarbonyl, methylsulfonyl, in each case optionally simply or phenylcarbonyl, phenoxycarbonyl or benzyl substituted twice, identically or differently in phenyl by fluorine, chlorine, methyl or trifluoromethyl, or for cyclopropyl

R ⁴ and R ⁵ independently of one another particularly preferably represent hydrogen or the radicals -COR ⁶ , -COOR ⁷ or -SO ₂ R ⁸ , where

R ⁶ , R ⁷ and R ⁸ independently of one another particularly preferably represent Cj-

C ₈ -alkyl, C _j -C -haloalkyl having 1 to 5 identical or different

Halogen atoms, such as fluorine, chlorine or bromine atoms, C ₁ -C ₂ -alkoxy- C _r C ₄ -alkyl, C _r C ₂ -alkylthιo-C _r C ₄ -alkyl, C _r C ₄ -alkylcarbonyloxy-

C _j ^ -al yl, C ₁ -C ₂ alkoxycarbonyl-C ₁ -C ₄ alkyl, C ₂ -C alkenyl, C ₂ - C4 haloalkenyl having 1 to 5 identical or different halogen atoms, such as fluorine or chlorine atoms , C ₂ -C ₄ -Alkιnyl, C ₂ -C ₄ -halogen- alkynyl with 1 to 5 identical or different halogen atoms, such as fluorine or chlorine atoms; for in each case monosubstituted to trisubstituted, identically or differently, C3-C6-cycloalkyl, C ₃ -C ₆ -cycloalkyl-Cι-C ₂ -alkyl, C ₃ -C ₆ -cycloalkyloxy-Cι-C ₂ -alkyl and C ₃ -C ₆ cycloalkylthio-C _r

C alkyl, suitable substituents being in each case halogen, Cι-C4-alkyl, C _j - C same -halogenoalkyl having 1 to 5 or different halogen atoms, such as fluorine or chlorine atoms, Cι-C - alkoxy, C ₂ -C _j -Halogenalk - Oxy with 1 to 5 identical or different halogen atoms, such as fluorine or chlorine atoms, C -C4 alkenyl, C ₂ -C ₄ haloalkenyl with 1 to 5 identical or different halogen atoms, such as fluorine or chlorine atoms, nitro or cyano in question come, alkyl in each case optionally mono- to trisubstituted by identical or different in the ring substituted phenyl, phenyl-C ₁ -C _2, phenoxy-C -C ₂ - alkyl or phenylthio-C ₁ -C ₂ alkyl, substituents being each

Halogen, nitro, cyano, C _j -C ₂ alkyl, C ₁ -C ₂ haloalkyl having 1 to 5 identical or different halogen atoms, such as fluorine or chlorine atoms, C 1 -C ₄ alkoxy, C _j -C ₄ haloalkoxy 1 to 5 identical or different halogen atoms, such as fluorine or chlorine atoms, Cι-C ₂ - alkylthio, Cι-C ₂ -halogenoalkylthio having 1 to 5 identical or different halogen atoms, such as fluorine or chlorine atoms, C ₂ -C ₄ alkenyl, C ₂ -C ₄ haloalkenyl having 1 to 5 identical or different halogen atoms, such as fluorine or chlorine atoms, and also C ₁ -C ₂ alkoxycarbonyl or C ₁ -C ₂ alkylcarbonyloxy, or are suitable for the following, if appropriate simply up to triple, identical or differently substituted heterocycles:

-w— _j , where in each case N

Fluorine, chlorine, bromine, nitro, cyano, methyl, ethyl, n- or l-propyl, n-, l-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, methylthio,

-CF ₃ , -CHF ₂ , -OCF ₃ and -OCHF _{2 come} into question

and where

Z for C 1 -C ₄ -alkyl, in particular methyl or ethyl, C _j -C ^ -

Alkylcarbonyl, such as in particular methylcarbonyl or ethylcarbonyl, or for optionally single or double, identical or different by C _! -C ₄ - alkyl, such as in particular methyl or ethyl, halogen, such as in particular fluorine or chlorine, C _j - C ₄ haloalkyl, such as in particular tnfluoromethyl, CC ₄ -alkoxy, such as in particular methoxy, and C _j -C ₄ - Halogenalkoxy, such as, in particular, Tπfluormethoxy substituted phenylsulfonyl

X ¹ and X ² independently of one another particularly preferably represent fluorine, chlorine,

Nitro, cyano, methyl, methoxy or tnfluoromethyl

m and n independently of one another are particularly preferably 0, 1 or 2, in particular 0 or 1

Y particularly preferably represents one of the radicals -CH ₂ -, -CH (CH ₃ ) -,

-CH (C ₂ H ₅ ) -, -CH (nC ₃ H ₇ ) -, -CH (ι-C ₃ H ₇ ) -, -CH ₂ CH ₂ -, -CH (OH) -, -CH (OCH ₃ ) -, -CH (O-CO-CH ₃ ) -, -CH (CN) -, -CHF-, -CHC1-, -CH (- <) - -CH = CH- or -CH ₂ O-.

Het very particularly preferably represents one of the heterocycles

R ¹ very particularly preferably represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl; CH ₂ C1, CH ₂ Br, methoxy, ethoxy, methylthio or cyclopropyl.

R ² very particularly preferably represents hydrogen, chlorine, bromine, cyano, nitro, methoxycarbonyl, ethoxycarbonyl, methylthio, methylsulfinyl or methylsulfonyl; or

R ¹ and R ² very particularly preferably, together with the carbon atoms to which they are attached, represent a 6-membered carbocyclic ring which may be mono- or disubstituted, identically or differently, by fluorine, chlorine, methyl, nitro or cyano.

R ³ very particularly preferably represents hydrogen, methyl, ethyl, methoxymethyl, ethoxymethyl, methylcarbonyl, methoxycarbonyl, ethoxycarbonyl, i-propoxycarbonyl, allyloxycarbonyl or phenoxycarbonyl.

R ⁴ and R ⁵ independently of one another very particularly preferably represent hydrogen or the radicals -COR ⁶ , -COOR ⁷ or -SO ₂ R ⁸ , where

R ⁶ , R ⁷ and R ⁸ independently of one another very particularly preferably represent methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, n-pentyl, 2,2-dimethylpropyl , n-hexyl, n-heptyl, n-octyl; for 2-propenyl, 1-propenyl, 2-propynyl, for chloromethyl, 2-chloroethyl, trifluoromethyl, 2,2,2-trifluoroethyl; for methoxymethyl, methoxyethyl, ethoxymethyl, for each optionally one to three times, identical or different by methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy,

Ethoxy, fluorine, chlorine, bromine or 2,2-dichlorovinyl-substituted cyclopropyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclopentylmethyl or cyclohexylmethyl, each optionally optionally up to three times, identically or differently, by fluorine, chlorine, bromine, cyano, nitro , Methyl, ethyl, methoxy,

Ethoxy, methylthio, trifluoromethyl, trifluoromethoxy, trifluoromethyl-thio, methoxycarbonyl, ethoxycarbonyl or methylcarbonyloxy substituted phenyl or benzyl, or for an optionally single to triple, identical or different substituted heterocycle from the series 1-furyl, 2-

Furyl, 1-thienyl, 2-thienyl, 1,3-oxazol-2-yl, 1,3-oxazol-4-yl, 1,3-thiazol-2-yl, 1,3-thiazol-4-yl, l, 2-oxazol-3-yl, l, 2-oxazol-4-yl, 1,2-oxazol-5-yl, l, 2-thiazol-3-yl, l, 2-thiazol-4-yl, l, 2-thiazol-5-yl, 3-pyrazolyl, 4-pyrazolyl, 5-pyrazolyl, 2-pyridyl, 3-pyridyl and 4-pyridyl, with fluorine, chlorine, bromine, nitro, cyano as substituents,

Methyl, ethyl, methoxy, ethoxy or trifluoromethyl come into question

X ¹ and X ² independently of one another very particularly preferably represent fluorine, chlorine, cyano, methyl or trifluoromethyl

m and n independently of one another very particularly preferably represent 0 or 1, in particular 0

Y very particularly preferably stands for -CH ₂ -, -CH (CH ₃ ) - or -CH ₂ O-, in particular for -CH ₂ - or -CH (CH ₃ ) - In a preferred embodiment, one of the substituents R ⁴ or R ^{5 is} hydrogen.

Preferred groups of compounds according to the invention are in each case the substances of the formulas (IA) to (ID):

in which

R ¹ , R ² , R ³ , R ⁴ , R ⁵ , X ¹ , X ² , Y, m and n represent the abovementioned general, preferred, particularly preferred and very particularly preferred meanings. Preferred groups of compounds according to the invention are also in each case the substances of the formulas (IA-1) to (IA-8), (IB-1) to (IB-8), (IC-1) to (IC-8) and (ID -1) to (ID-8):

- NH - COR ⁶ (IA-2)

in which R ¹ , R ² , R ³ , R ⁶ , R ⁷ and R ⁸ stand for the abovementioned general, preferred, particularly preferred and very particularly preferred meanings.

in which R ¹ , R ² , R ³ , R ⁶ , R ⁷ and R ⁸ stand for the abovementioned general, preferred, particularly preferred and very particularly preferred meanings.

O, J- ⁷ W NH - COOR '(IC-3)

in which R ¹ , R ³ , R ⁶ , R ⁷ and R ⁸ stand for the abovementioned general, preferred, particularly preferred and very particularly preferred meanings.

in which

R ¹ , R ³ , R ⁶ , R ⁷ and R ⁸ stand for the abovementioned general, preferred, particularly preferred and very particularly preferred meanings.

The general or preferred definitions or explanations given above apply to the end products and the starting and intermediate products accordingly. These residual definitions can be combined with one another, i.e. also between the respective preferred areas

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 there is a combination of the meanings listed above as being particularly preferred.

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

In the radical definitions given above, alkyleneoxy or -CH ₂ O- is to be understood such that R ⁴ in formula (I) is linked to the oxygen of the alkyleneoxy or -CH ₂ O radical

In addition to the preparation examples, the following compounds may be mentioned individually Table 1

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

Rl = C ₂ H ₅

R ² = C1

R ⁴ = as listed below:

R ⁴ R ⁴ R ⁴

-COCH ₂ CH = CH ₂ -COOC ₂ H ₅ -SO ₂ C ₆ H ₁₃ -n

-COCH ₂ C≡CH -COOC ₃ H ₇ -ι -so ₂ - <]

-COCH ₂ Cl -COOC ₄ H ₉ -n -S ° Γ (H]

-COOC ₄ H ₉ -t -SO ₂ CH ₂ CH = CH ₂

-COOCH ₂ C ₄ H ₉ -t

-co- ^ -COOC ₆ H ₁₃ -n -so ₂ - 2> -cι

Table 2

Compounds in Table 2 correspond to the general formula (Ia), in which R ¹ = CH ₃

R ² and R ⁴ = as listed in Table 1

Table 3

Compounds in Table 3 correspond to the general formula (Ia), in which

R ² = Br

R ¹ and R ⁴ = as listed in Table 1

Table 4

Compounds in Table 4 correspond to the general formula (Ia), in which

R ² = CN

R ¹ and R ⁴ = as listed in Table 1 Table 5

Compounds in Table 5 correspond to the general formula (Ia) in which R ² = HR ¹ and R ⁴ = as listed in Table 1.

Table 6

Compounds in Table 6 correspond to the general formula (Ib), in which R ¹ = C ₂ H ₅ or CH ₃ , R ² = Cl, Br, CN or H and R ⁴ = as listed in Table 1.

Table 7

Compounds in Table 7 correspond to the general formula (Ib-1), in which R ⁴ = as listed in Table 1.

Table 8

Compounds in Table 8 correspond to the general formula (Ib-2), in which R ⁴ = as listed in Table 1.

Table 9

Compounds in Table 9 correspond to the general formula (Ic), in which

Rl = C ₂ H ₅

R ⁴ = as listed in Table 1.

Table 10

Compounds in Table 10 correspond to the general formula (Ic), in which R ¹ = iC ₃ H ₇ R ⁴ = as listed in Table 1.

Table n

Compounds in Table 1 1 correspond to the general formula (Ic) in which R ¹ = CH ₃

R ⁴ = as listed in Table 1.

Table 12

Compounds in Table 12 correspond to the general formula (Ic), in which

R ⁴ = as listed in Table 1. Table 13

Compounds in Table 13 correspond to the general formula (Id) in which R ¹ = C ₂ H ₅ , iC ₃ H ₇ , CH ₃ or <^ | and R ⁴ = as listed in Table 1.

If, for example, 4-chloro-3-methyl-5- [4- (4-nitro-phenoxy)] phenyl-acetylamino-isothιazole and iron powder in the presence of hydrochloric acid are used as starting materials in process (a), the course of the process according to the invention can be carried out are represented by the following reaction scheme

If, for example, 5- [4- (4-aminophenoxy)] phenyl-acetylamino-4-chloro-3-methyl-isothiazole and pivalic acid chloride are used as starting materials in process (b), the course of the process according to the invention can be represented by the following reaction scheme :

If, for example, 5-amino-4-chloro-3-ethyl-isothiazole and 4- (4-t-butylcarbonylaminophenoxy) phenylacetic acid chloride are used as starting materials in process (c), the course of the process according to the invention can be determined by the following

Reaction scheme can be reproduced

+ Cl - CO-CH ₂ - C / ° \ VNH-CO-C (CH ₃ ) ₃

The nitro derivatives of the formula (II) required as starting materials for carrying out the process (a) according to the invention are largely known (cf., for example, WO 95/31 448, DE-A-195 42 372, WO 93/04 580, WO 95 / 18 795 and WO 97/26 251) and / or by the processes specified there

The amino derivatives of the formula (1-1) required as starting materials for carrying out process (b) according to the invention are compounds according to the invention

The compounds of the formula (III) which are also to be used as starting materials in process (b) according to the invention are generally known compounds of organic chemistry and / or can be obtained by generally known and customary processes The amino heterocycles of the formula (IV) required as starting materials for carrying out process (c) according to the invention are largely known (cf., for example, WO 95/31 448, DE-A-95 42 372, DE-A-22 49 162, WO 93 / 19 054, WO 94/21 617, J Med Chem 1989. 32, 1970-77, J Prakt Chem 1989. 331, 369-74, Tetrahedron 1971. 2581, J Org Chem 1952. 547, J Het Chem 1970. 81, J Org Chem 1981.

2134, J Heterocycl Chem 1987. 14, 1413, JP 60 109 571, EP-A 0 455 356, Chem Ber 1954, 87, 57, and Chem Ber 1956, 89, 2742) and / or can be obtained by the processes specified therein

The compounds of the formula (V) to be used as starting materials in process (c) according to the invention are new. They are obtained by acid derivatives of the formula (VI)

in which

R ⁴ " ¹ , R ⁵ , X ¹ , X ² , Y, m and n have the meaning given above,

activated in a generally known and customary manner, for example by reaction with thionyl chloride, oxalyl chloride, phosphorus oxychloride, carbonyldiimidazole and similar activation reagents (see also general textbooks on organic chemistry)

The acid derivatives of the formula (VI) are also new. They are obtained by known or obtainable in a customary manner (see, for example, US

4 168 385) aminophenoxyphenyl acid derivatives of the formula (VII)

in which

X ¹ , X ² , Y, m and n have the meaning given above,

with compounds of the formula (III)

GR ⁴ " ¹ (HI), in which

G and R ⁴ " ^{1 have} the meaning given above,

and optionally then with compounds of the formula (purple)

G-R5-1 (purple), in which

G has the meaning given above and

R ⁵ " ^{1 represents} the meanings of R ⁵ , except hydrogen,

implemented in accordance with the conditions of process (b) according to the invention.

The reduction according to process (a) described above for the preparation of the compounds of the formula (I) takes place either by means of base metals, such as iron, tin or zinc, preferably in the presence of an acid, such as hydrochloric acid or sulfuric acid; or by hydrogenation with molecular hydrogen in the presence of conventional catalysts, such as platinum oxide, palladium / carbon or Raney nickel. In some cases it proves to be advantageous to carry out the reduction according to process (a) by means of other customary reducing agents. Hydrazine, sodium hydrogen sulfide or formic acid in the presence of palladium / carbon may be mentioned as examples

The process (a) described above for the preparation of the compounds (I) is optionally carried out in the presence of a diluent. Alcohols, such as methanol and ethanol, and mixtures of alcohols with water can preferably be used

When carrying out process (a) according to the invention, the reducing agent is generally used in excess

The reaction temperatures can be varied within a wide range in process (a) described above. In general, temperatures between 0 ° C and 150 ° C, preferably between 20 ° C and 100 ° C.

The processes (b) and (c) described above for the preparation of the compounds of the formula (I) are carried out in the presence of a diluent. All customary solvents can be used as diluents

Halogenated aliphatic or aromatic hydrocarbons, ethers or nitriles such as cyclohexane, toluene, chlorobenzene, chloroform, dichloromethane, dichloroethane, dioxane, tetrahydrofuran, diethyl ether or acetonitrile are preferably usable

The processes (b) and (c) described above for the preparation of the compounds of the formula (I) are carried out in the presence of a base.

All customary proton acceptors can be used as bases. Alkali or alkaline earth metal hydroxides, alkali or alkaline earth metal carbonates or hydrogen carbonates or nitrogen bases are preferably usable. trium 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 the processes (a) and (b) described. In general, temperatures between -40 ° C and + 200 ° C, preferably between 0 ° C and 100 ° C.

When carrying out the processes (a) and (b) described above for the preparation of the compounds of the formula (I), 1 to 2 mol, preferably 1 to 1.5 mol, are generally employed per mol of the amino derivative of the formula (Ia) Compound of formula (III); and per mole of 5-aminoisothiazole of the formula (IV) 1 to 2 moles, preferably 1 to 1.5 moles of a compound of the formula (V) It has proven advantageous in some cases to use the 5-aminoisothiazoles of the formula (IV) in the form of their hydrohalides, such as, in particular, as hydrochlorides.

The end products are worked up and isolated in a generally known manner.

With good plant tolerance and favorable toxicity to warm-blooded animals, the active substances are suitable for combating animal pests, in particular insects, arachnids and nematodes, which occur in agriculture, in forests, in the protection of stored goods and materials, and in the hygiene sector. They can preferably be used as pesticides. They are effective against normally sensitive and resistant species as well as 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, for example, Geophilus carpophagus and Scutigera spec. From the order of the Symphyla, for example, Scutigerella immaculata. From the order of the Thysanura, for example Lepisma saccharina. From the order of the Collembola, for example Onychiurus armatus.

From the order of the Orthoptera e.g. 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 e.g. Forficula auricularia.

From the order of the Isoptera e.g. 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 spp., Macrosiphum avenae, Myzus spp., Phorodon humuli, Rhopa- losiphum padi, Empoasca spp., Euscelis bilobatus, Nephotettixcincticeps, Lecanium corni, Saissetia oleae, Laodelphax striatellus, Nilaparvata lugens, Aonidiella aurantii, Aspidiotus hederae, spp Pseudococcus. , Psylla spp. From the order of the Lepidoptera e.g. Pectinophora gossypiella, Bupalus piniarius,

Cheimatobia brumata, Lithocolletis blancardella, Hyponomeuta padella, Plutella maculipennis, Malacosoma neustria, Euproctis chrysorrhoea, Lymantria spp., Bucculatrix thurberiella, Phyllocnistis citrella, Agrotis spp., Euxoaothpppp., Fuxiothppa, Fux. 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 po- dana, Capua reticulana, Choristoneura famiferana, Clysona ambiganana, Clysia ambiganana, Toric 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., Oryamensisilus Anthonomus spp, Sitophilus spp, Otiorrhynchus sulcatus, Cosmopohtes sordidus, Ceuthorrhynchus assimihs, Hypera postica, Dermestes spp, Trogoderma spp, Anthrenus spp, Attagenus spp, Lyctus spp, Me gethes aeneus, Niptinium sppyl, Siptidium spp, Siptidium spp molitor, Agπotes spp, Conoderus spp, Melolontha melolontha, Amphimallon solstitia s, Costelytra zealandica

From the order of the Hymenoptera e.g. Dipπon spp, Hoplocampa spp, Lasius spp, Monomoπum pharaonis, Vespa spp From the order of the Diptera e.g. B Aedes spp, Anopheles spp, Culex spp, Drosophila melanogaster, Musca spp, Fannia spp, Calliphora erythi spp, Chrysomyia spp, Cuterebra spp, Gastrophilus spp, Hyppobosca spp, Stomoxys spp, Oestrus spp, Hypoderma spp, Tabanus spp, Tanma spp, Bibio hortulanus, Oscinella fπt, Phorbia spp, Pegomyia hyoscyami, Tipacus palitosa, Dacatus palitosa, Ceratitis capitata the order of the Siphonaptera e.g. Xenopsylla cheopis, Ceratophyllus spp

From the order of the Arachnida, for example Scorpio maurus, Latrodectus mactans From the order of the Acaπna, for example Acarus siro, Argas spp, Ornithodoros spp, Dermanyssus gallinae, Eπophyes πbis, Phyllocoptruta oleivora, Boophilus spp, Rhipicexa spp, Amblylyomma spp, Amblylyomma spp, I spp, Psoroptes spp, Choπoptes spp, Sarcoptes spp, Tarsonemus spp, Bryobia praetiosa, Panonychus spp, Tetranychus spp

Plant parasitic nematodes include, for example, Pratylenchus spp, Radopholus simihs, Ditylenchus dipsaci, Tylenchulus semipenetrans, Heterodera spp, Globodera spp, Meloidogyne spp, Aphelenchoides spp, Longidorus spp, Xφhinema spp, Tnchchod

The compounds of the formula (I) according to the invention are notable in particular for a high insecticide and akaπzide effect

They can be used with particularly good success for combating plant-damaging insects, such as, for example, against the horseradish leaf beetle larvae (Phaedon cochleaπae), the green rice leafhopper (Nephotettix cinctπceps) and the caterpillars of the owl butterfly (Spodoptera frugiperda) or for combating plant-damaging ones Use mites, for example against the common spider mite (Tetranychus urticae).

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 made in a known manner, e.g. 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 foam-generating agents.

If water is used as an extender, e.g. organic solvents can also be used as auxiliary solvents. The following are essentially suitable as liquid solvents: aromatics, such as xylene, toluene, or alkylnaphthalenes, chlorinated aromatics and chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chlorethylenes or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, e.g. Petroleum fractions, mineral and vegetable oils, alcohols such as butanol or glycol as well as their ethers and esters, ketones such as

Acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents such as dimethylformamide and dimethyl sulfoxide, and water.

Possible solid carriers are: e.g. Ammonium salts and natural rock flours, such as kaolins, clays, talc,

Chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and synthetic rock flour, such as highly disperse silica, aluminum oxide and silicates, are suitable as solid carriers for granules: e.g. broken and fractionated natural rocks such as calcite, marble, pumice, sepiolite, dolomite and synthetic granules inorganic and organic flours and granules of organic material such as sawdust, coconut shells, corn cobs and tobacco stalks; suitable emulsifiers and / or foam-generating agents are: for example nonionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene Fatty alcohol ethers, for example alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates and protein hydrolyzates; Possible dispersing agents are, for example, lignin sulfite waste liquor and methyl cellulose.

Adhesives such as carboxymethyl cellulose, natural and synthetic powdery, granular or latex-shaped polymers, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, and natural phospholipids such as cephalins and lecithins and synthetic phospholipids can be used in the formulations. Other additives can be mineral and vegetable oils.

Dyes such as inorganic pigments, e.g. Iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin, azo and metal phthalocyanine 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 of active compound, preferably between 0.5 and 90%.

The active substance according to the invention can be present 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, sterilants, bactericides, acaricides, nematicides, fungicides, growth-regulating substances or herbicides. Insecticides include, for example, phosphoric acid esters, carbamates, carboxylic acid esters, chlorinated hydrocarbons, phenylureas, substances produced by microorganisms, etc.

The following are particularly favorable mixed partners: Fungicides:

2-aminobutane; 2-anilino-4-methyl-6-cyclopropyl-pyrimidine; 2 ', 6'-dibromo-2-methyl-4'-trifluoromethoxy-4'-trifluoro-methyl-1, 3-thiazole-5-carboxanilide; 2,6-dichloroN- (4-trifluoromethylbenzyl) benzamide; (E) -2-methoxyimino-N-methyl-2- (2-phenoxyphenyl) acetamide; 8-hydroxyquinoline sulfate; Methyl- (E) -2- {2- [6- (2-cyanophenoxy) pyrimidine-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, cyprofüram, dichlorophen, diclobutrazole, dicloflomolanidol, dicloflomolanidol, dicloflomolanidol, dicloflomolanidol, dicloflomolanidol, dicloflomolanidol, dicloflomolanidol, dicloflomolanidol, dicloflomolanidol, diclomolanidol, dicloflomolanidol, dicloflomolanidol, dicloflomolanidol, diclomolanidol, dicloflomolonidol, diclofolomidol, diclofolomidol, diclozolidl , Dinocap, diphenylamine,

Dipyrithion, Ditalimfos, Dithianon, Dodine, Drazoxolon, Edifenphos, Epoxyconazole, Ethirimol, Etridiazol,

Fenarimol, Fenbuconazole, Fenfüram, Fenitropan, Fenpiclonil, Fenpropidin, Fen- propimorph, Fentinacetat, Fentinhydroxyd, Ferbam, Ferimzone, Fluazinam, Flu-dioxonil, Fluoromide, Fluquinconazole, Flusilazole, Flusulfamide, Flutolafosol, Fol- Fthalides, fuberidazole, furalaxyl, furmecyclox, guazatine,

Hexachlorobenzene, hexaconazole, hymexazole, imazalil, imibenconazole, iminoctadine, Iprobefos (IBP), iprodione, isoprothiolane, kasugamycin, copper preparations, such as: copper hydroxide, copper naphthenate, copper oxychloride, copper sulfate, copper oxide, and copper oxide, oxin-man mixture , Mancozeb, Maneb, Mepanipyrim, Mepronil, Metalaxyl, Metconazol, Methasulfocarb, Methfüroxam, Metiram, Metsulfovax, Myclobutanil, Nickel-dimethyldithiocarbamate, Nitrothal-isopropyl, Nuarimol, Ofürace, Oxadixyoxoxoxinoxoxoxoxinoxinoxoxoxinoxinoxoxoxinoxoxinoxoxinoxoxin

Pefürazoate, penconazole, pencycuron, phosdiphen, phthalide, pimaricin, piperalin, polycarbamate, polyoxin, probenazole, prochloraz, procymidon, propamocarb, proconazole, propineb, pyrazophos, pyrifenox, pyrimethanil, pyroquilon, Quintozen (PCNB), sulfur and sulfur preparations,

Tebuconazole, tecloftalam, tecnazen, tetraconazole, thiabendazole, thicyofen, thiophanate-methyl, thiram, tolclophos-methyl, tolylfluanid, triadimefon, triadimenol, triazoxide, trichlamid, tricyclazole, tridemorph, triflorolizol, triflorolizol, triflorolizole,

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, Acephat, Acrinathrin, Alanycarb, Aldicarb, Alphamethrin,

Amitraz, Avermectin, AZ 60541, Azadirachtin, Azinphos A, Azinphos M, Azocyclotin,

Bacillus thuringiensis, Bendiocarb, Benfüracarb, Bensultap, Betacyfluthrin, Bifenthrin, BPMC, Brofenprox, Bromophos A, Bufencarb, Buprofezin, Butocarboxin, Butyl-pyridaben,

Cadusafos, Carbaryl, Carbofüran, Carbophenothion, Carbosulfan, Cartap, CGA 157 419, CGA 184699, Chloethocarb, Chlorethoxyfos, Chlorfenvinphos, Chlorfluazuron, Chlormephos, Chlorpyrifos, Chlorpyrifos M, Cis-Resmethrin, Clocytezhrinhrinhrinhrinhrinhrinhrin, Clofythrinhrinhrinhrin, Clofythrinhrinhrinhrin, Clofythrinhrinhrinhrinhrin, Clofythrinhrinhrinhrin, Clofythrinhrinhrinhrinhrinhrin, Clofythrinhrinhrinhrinhrin, Clofythrinhrinhrinhrinhrinotin Cyhexatin, cypermethrin, cyromazine,

Deltamethrin, Demeton M, Demeton S, Demeton-S-methyl, Diafenthiuron, Diazinon, Dichlofenthion, Dichlorvos, Dicliphos, Dicrotophos, Diethion, Diflubenzuron, Dimethoat, Dimethylvinphos, Dioxathion, Disulfoton, Ethifenin, Ethifen, Ethifenphonofen, Emifenphonofen, Emifenphonofen, Emifenphonofen, Emifenphosofen, Emifenphonofen, Emifenphonofen, Emifenphonofen, Emifenphonofen Ethofenprox, ethoprophos, etrimphos,

Fenamiphos, Fenazaquin, Fenbutatinoxid, Fenitrothion, Fenobucarb, Fenothiocarb, Fenoxycarb, Fenpropathrin, Fenpyrad, Fenpyroximat, Fenthion, Fenvalerate, Fipronil, Fluazinam, Flucycloxuron, Flucythrinat, Flufenoxuron, Flufenprox, Fluvalinate, Fonophos, Formothion, Fosthiazat, Fubfenprox, Furathiocarb, 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, Omethoyd, Oxofon, Oxamon ,

Parathion A, Parathion M, Permethrin, Phenthoat, Phorat, Phosalon, Phosmet, Phosphamidon, Phoxim, Pirimicarb, Pirimiphos M, Pirimiphos A, Profenofos, Promecarb, Propaphos, Propoxur, Prothiofos, Prothoat, Pymetroion, Pyradaphophone, Pyrada phylophone Pyresmethrin, Pyrethrum, 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, Thionazine, Thuringiensin, Tralomenethriazonium, Triaromenhriazonium, Triaromenhriazonium

Trichlorfon, triflumuron, trimethacarb, vamidothione, XMC, xylylcarb, YI 5301/5302, zetamethrin.

A mixture with other known active ingredients, such as herbicides or with fertilizers and growth regulators, is also possible.

The active compounds according to the invention can furthermore be present in their commercially available formulations and in the use forms prepared from these formulations in a mixture with synergists. Synergists are compounds through which the action of the active ingredients is increased 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

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 pests, but also in the veterinary sector against deep parasites (ectoparasites) such as tick ticks, leather ticks, rough mites, running mites, flies (stinging and licking), parasitic fly larvae, lice, Hair warmer, feather nooks and fleas These parasites include

From the order of the Anoplurida, for example Haematopinus spp, Lmognathus spp, Pediculus spp, Phtirus spp, Solenopotes spp

From the order of the Mallophagida and the subordinates Amblycenna and I lsscidhmnouciseCriiiniiaα z. B ι_> T j. π 1 πmuecniuopjjounii s apμpμ ,, M iviecniiov pjjounn s apμpμ ,, T iriimnoutiounu s »pjjpμ .. ,, B ι_> o» vvi_coul_aα s apj p | _, s enpnp, LT perp.iilk s-rn »n , F Dianmmaalhinnan <s_npnp, T Trriirchhnordlpercttpecs snppn, F Ffelliirc.nollan e snpnp

From the order Diptera and the subordinates Nematoceπna and Brachycenna e.g. Aedes spp, Anopheles spp, Culex spp, Simu um spp, Eusimu um spp, Phlebotomus spp, Lutzomyia spp., Culicoides spp, Chrysops spp, Hybomitra spp, Tabylotus spp, Atylotus spp , Haematopota spp, Phihpomyia spp., Braula spp, Musca spp, Hydrotaea spp, Stomoxys spp, Haematobia spp, Morelha spp, Fannia spp, Glossina spp, Calliphora spp, Luci a spp, Chrysomyia spp, Wohlfahrtia spp, Sarestrophaga spp , Hypoderma spp, Gasterophilus spp, Hippobosca spp, Lipoptena spp, Melophagus spp From the order of the Siphonapterida, for example Pulex spp., Ctenocephalides spp., Xenopsylla spp., Ceratophyllus spp ..

From the order of the Heteropterida e.g. Cimex spp., Triatoma spp., Rhodnius spp.,

Panstrongylus spp ..

From the order of the Blattarida e.g. Blatta orientalis, Periplaneta americana, Blattela germanica, Supella spp ..

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

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

For example, they show a good development-inhibiting effect against fly larvae from Lucilia cuprina as well as a good inhibition of egg laying in Boophilus microplus.

The active compounds of the formula (I) according to the invention are also suitable for controlling arthropods which are used in agricultural animals, e.g. Cattle, sheep, goats, horses, pigs, donkeys, camels, buffalo, rabbits, chickens, turkeys, ducks, geese,

Bees, other domestic animals such as dogs, cats, house birds, aquarium fish and so-called experimental animals such as hamsters, guinea pigs, rats and mice are infected. By fighting these arthropods, deaths and Reductions in performance (for meat, milk, wool, skin, eggs, honey, etc.) are reduced, so that the use of the active compounds according to the invention enables more economical and simple animal husbandry

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, drinks, 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 necklaces, ear tags, tail tags, tape bands, holders, 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 are examples and preferably - but without limitation -

Called insects

Beetle like

Hylotrupes bajulus, Chlorophorus pilosis, Anobium punctatum, Xestobium rufo- viUosum, Ptilinus pecticornis, Dendrobium pertinex, Ernobius mollis, Priobium carpini, Lyctus brunneus, Lyctus afπcanus, Lyctus planicol s, Lyctus neaoxes alys spec Tryptodendron spec. Apate monachus, Bostrychus capucins, Heterobostrychus brunneus, Sinoxylon spec. Dinoderus minutus.

Hymenoptera such as Sirex juvencus, Urocerus gigas, Urocerus gigas taignus, Urocerus augur.

Termites like

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

Bristle tails like Lepisma saccarina.

In the present context, technical materials include non-living ones

Understand 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 ingredients as such, in the form of concentrates or generally customary formulations such as powders, granules, solutions, suspensions, emulsions or

Pastes can be applied. The formulations mentioned can be prepared in a manner known per se, for example 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, if appropriate, color - substances and pigments as well as other 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 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 oil-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 alkyl benzene, are used as such 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 are advantageous from 250 to 350 ° C, petroleum or aromatics with a boiling range of 160 to 280 ° C, turpentine oil and the like

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 spindle oil and / or monochloronaphthalene, preferably α-mono- chloronaphthalene used

The organic volatile oily or oil-like solvents with a

Evaporation rate 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 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 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, Ester or the like for use

In the context of the present invention, the known organic-chemical binders are the water-thinnable and / or synthetic resins soluble or dispersible or emulsifiable in the organic chemical solvents used and / or binding drying oils, in particular binders consisting of or containing an acrylate resin, a vinyl resin, e.g. 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.

The synthetic resin used as a binder can be used in the form of an emulsion, dispersion or solution. Bitumen or bituminous substances up to 10% by weight can also be used as binders. In addition, known dyes, pigments, water-repellent agents, odor correctors and inhibitors or anticorrosive agents and the like can be 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 organic chemical binder. According to the invention, alkyd resins with an oil content of more than 45% by weight, preferably 50 to 68%, are preferred % By weight used

All or part of the binder mentioned can be replaced by a fixative (mixture) or a plasticizer (mixture). These additives are intended to prevent volatilization of the active ingredients and crystallization or precipitation. 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 glycol or high molecular weight glycerol oleate, glycerol oleate, glycerol oleate, and glycerol oleate - ether, 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 ethylene benzophenone

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 preservation is achieved by industrial impregnation processes, e.g. vacuum, double vacuum or pressure processes.

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

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

Especially preferred mixing partners are insecticides, such as chlorpyriphos, phoxim, silafluofin, alphamethrin, cyfluthrin, cypermethrin, deltamethrin, per- methrin, imidacloprid, NI-25, flufenoxuron, hexaflumuron and triflumuron, and fungicides such as epoxyconazole, hexaconazole, azaconazole, propiconazole, Tebucon - Azoles, Cyproconazole, Metconazole, Imazalil, Dichlorfluanid, Tolylfluanid, 3-Iodo-2-propynyl-butylcarbamate, N-Octyl-isothiazolin-3-one and 4,5-Dichlor-N-octylisothiazo-lin-3-one

The active compounds according to the invention also have a strong microbicidal action and can be used practically to combat unwanted microorganisms. The active ingredients are suitable for use as crop protection agents, in particular as fungicides.

Fungicidal agents in crop protection are used to combat plasmidiophoromycetes, Oomycetes, Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes, Deuteromycetes

Bactericidal agents are used in crop protection to combat Pseudomonadaeae, Rhizobiaceae, Enterobacteriaceae, Corynebacteriaceae and Streptomycetaceae. Some pathogens of fungal and bacterial diseases that fall under the generic names listed above may be mentioned as examples, but not by way of limitation:

Xanthomonas species, such as, for example, Xanthomonas campestris pv. Oryzae; Pseudomonas species, such as, for example, Pseudomonas syringae pv. Lachrymans;

Erwinia species, such as, for example, Erwinia amylovora;

Pythium species, such as, for example, Pythium ultimum;

Phytophthora species, such as, for example, Phytophthora infestans;

Pseudoperonospora species, such as, for example, Pseudoperonospora humuli or Pseudoperonospora cubensis;

Plasmopara species, such as, for example, Plasmopara viticola;

Bremia species, such as, for example, Bremia lactucae;

Peronospora species, such as, for example, Peronospora pisi or P. brassicae;

Erysiphe species, such as, for example, Erysiphe graminis; Sphaerotheca species, such as, for example, Sphaerotheca Fülliginea;

Podosphaera species, such as, for example, Podosphaera leucotricha;

Venturia species, such as, for example, Venturia inaequalis;

Pyrenophora species, such as, for example, Pyrenophora teres or P. graminea

(Conidial form: Drechslera, Syn: Helminthosporium); Cochliobolus species, such as, for example, Cochliobolus sativus

(Conidial form: Drechslera, Syn: Helminthosporium);

Uromyces species, such as, for example, Uromyces appendiculatus;

Puccinia species, such as, for example, Puccinia recondita;

Sclerotinia species, such as, for example, Sclerotinia sclerotiorum; Tilletia species, such as, for example, Tilletia caries;

Ustilago species, such as, for example, Ustilago nuda or Ustilago avenae;

Pellicularia species, such as, for example, Pellicularia sasakii;

Pyricularia species, such as, for example, Pyricularia oryzae;

Fusarium species, such as, for example, Fusarium culmorum; Botrytis species, such as, for example, Botrytis cinerea;

Septoria species, such as, for example, Septoria nodorum;

Leptosphaeria species, such as, for example, Leptosphaeria nodorum;

Cercospora species, such as, for example, Cercospora canescens; Alternaria species, such as, for example, Alternaria brassicae, Pseudocercosporella species, such as, for example, Pseudocercosporella herpotrichoides.

The fact that the active ingredients are well tolerated by plants in the concentrations required to combat plant diseases allows treatment above ground

Parts of plants, of seedlings, and of the soil.

For example, they can be used with particularly good success against the pathogen of the downy vine mildew (Plasmopara viticola) and also against the rice stain disease (Pyricularia oryzae)

In addition, they show a broad in vitro activity against phytopathogenic fungi

The active compounds according to the invention can, when used as fungicides as such, in

In the form of their commercially available formulations or the use forms prepared from them, such as ready-to-use solutions, suspensions, wettable powders, pastes, soluble powders, dusting agents and granules. They are used in the customary manner, for example by pouring, spraying, spraying, scattering, foaming, Brushing etc. It is also possible to use the active ingredients according to the ultra-low

Apply volume method or inject the active ingredient preparation or the active ingredient into the soil. The seeds of the plants can also be treated.

In the treatment of parts of plants, the drug concentrations in the

Application forms can be varied over a wide range: they are generally between 1 and 0.0001% by weight, preferably between 0.5 and 0.001% by weight

In the seed treatment, amounts of active ingredient are generally from 0.001 to

50 g per kilogram of seed, preferably 0.01 to 10 g When treating the soil, active ingredient concentrations of 0.00001 to 0.1% by weight, preferably 0.0001 to 0.02% by weight, are required at the site of action.

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

Manufacturing examples

Example A-l

(Method a)

2.5 g (5.9 mmol) of 4-chloro-3-methyl-5- [4- (4-nitrophenoxy)] phenylacetylaminoisothiazole and 2.0 g (35.4 mmol) of iron powder are dissolved in 50 ml 50% ethanol is heated to the reflux temperature and 0.16 ml of 98% hydrochloric acid in 5 ml of 50% ethanol are added dropwise. The reaction mixture is heated for 3 hours

Reflux and then hot filtered. The filtrate is concentrated in vacuo to give 1.2 g (55% of theory) of 5- [4- (4-aminophenoxy)] phenylacetylamino-4-chloro-3-methyl-isothιazole, melting point 226 ° C.

Example A-2

(Method b)

0.78 g (1.9 mmol) of 5- [4- (4-aminophenoxy)] phenylacetylamino-4-chloro-3-methyl-isothiazole (Example 1) are dissolved in 20 ml of dichloromethane and 0.3 g (3.8 mmol)

Pyridine added Then 0.25 g (2.1 mmol) of pivalic acid chloride in 2 ml of dichloromethane are added dropwise with stirring and the reaction mixture is stirred at 25 ° C. for 18 hours. The reaction solution is then washed successively with water and 10% strength hydrochloric acid, dried and concentrated 0.8 g (80% of theory) of 5- [4- (4-t-butyl-carbonylaminophenoxy)] phenylacetylamino-4-chloro-3-methyl-isothiazole with a logP (pH 4.5) = 3 29 Example A-3

(Method b)

To 0.78 g (1.9 mmol) of 5- [4- (4-aminophenoxy)] phenylacetylamino-4-chloro-3-methyl-isothiazole (Example 1) in 10 ml of acetone, 0.32 g (3, 8 mmol) of sodium hydrogen carbonate were added and then 2.1 ml (2.1 mmol) of a 1 molar solution of isopropyl chloroformate in toluene was added dropwise. The reaction mixture was stirred at 25 ° C. for 18 hours, concentrated, the residue was taken up in water, filters off and dries.

0.6 g (69% of theory) of 5- [4- (4-isopropyloxycarbonylaminophenoxy)] phenylacetylamino-4-chloro-3-methyl-isothiazole with a logP (pH 4.5) = 3 43 are obtained

The following compounds according to the invention are obtained analogously to the preparation examples A-1 to A-3 or according to the general information on the preparation:

Table A

* ⁾ logP = decimal logarithm of the n-octanol / water distribution coefficient, determined by HPLC analysis on reversed phase with H ₂ O / CH ₃ CN Table B

Table B (continued)

" ⁾ logP = decimal logarithm of the n-octanol / water distribution coefficient, determined by HPLC analysis on reversed phase with H ₂ O / CH ₃ CN

Examples of use

Example A

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 treated by dipping into the active ingredient preparation of the desired concentration and populated with the green rice leafhopper (Nephotettix cincticeps) 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 compounds of the preparation examples Al, A-2, A-4, A-5, A-6, A-9 and Al 1 each achieve a death rate of 100% at an exemplary active ingredient concentration of 0.1% 6 days

Example B

Phaedon larval test

Solvent 7 parts by weight of dimethylformamide

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 level

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 cochleaπae) 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, the compounds of preparation examples Al, A-2, A-4, A-5, A-6, A-7, A-8, A-9, A-10 and Al 1, for example, produce an active compound concentration of 0.1% each a mortality of 100% after 7 days

Example C

Spodoptera frugiperda test

Solvent 7 weight unit 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 level

concentration

Cabbage leaves (Brassica oleracea) are treated by being dipped into the preparation of active compound of the desired concentration and populated with caterpillars of the owl butterfly (Spodoptera frugiperda) 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, the compounds of preparation examples Al, A-2, A-4, A-5, A-6, A-7, A-8, A-9, A-10 and Al 1, for example, produce an active compound concentration of 0.1% each a mortality of 100% after 7 days

Example D

Tetranychus test (OP-resistant / immersion treatment)

Solvent 3 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 to the desired concentrations with water containing emulsifier

Bean plants (Phaseolus vulgaπs), which are heavily infested with all stages of the common spider mite (Tetranychus urticae), are immersed in an active ingredient preparation of the desired concentration

After the desired time, the effect is determined in%. 100% means that all spider mites have been killed, 0% means that none of the spider mites have been killed

In this test, for example at an exemplary active ingredient concentration of 0.01%, the compound according to preparation example A-10 causes a death of 95% and the compound according to preparation example A-1 1 causes a death rate of 100%, in each case after 7 days

Example E

Plasmopara test (vine) / protective

Solvent 47 Weight point acetone

Emulsifier 3 weight alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration

To test for protective activity, young plants are sprayed with the preparation of active compound in the stated application rate. After the spray coating has dried on, the plants are inoculated with an aqueous spore suspension of Plasmapara viticola and then remain in an incubation cabin at approx

20 ° C and 100% relative humidity Then the plants are placed in a greenhouse for 5 days at about 21 ° C and about 90% relative humidity. The plants are then moistened and placed in an incubation cabin for 1 day

Evaluation is carried out 6 days after the inoculation. 0% means on

Efficiency that corresponds to that of the control, while an efficiency of 100% means that no infection is observed

In this test, for example at an application rate of 100 g / ha, the compound according to preparation example A-6 shows an efficiency of 94% and the

Compound according to production example A-10 an efficiency of 99% Example F

Pyricularia test (rice) / protective

Solvent. 2.5 parts by weight of acetone

Emulsifier - 0.06 parts 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 concentrate is diluted to the desired amount with water and the stated amount of emulsifier

concentration

To test for protective activity, young rice plants are sprayed with the active compound preparation in the stated application amount. After the spray coating has dried on, the plants are inoculated with an aqueous spore suspension of Pyricularia oryzae. The plants are then placed in a greenhouse at 100% relative atmospheric humidity and 25 ° C.

Evaluation is carried out 4 days after the inoculation. 0% means an efficacy which corresponds to that of the control, while an efficacy of

100% means that no infection is observed

In this test, for example at an exemplary application rate of 750 g / ha, the compounds according to Preparation Examples A-7, A-8 and A-10 each show an efficiency of 90% and the compounds according to Preparation Examples A-9 and Al 1 an efficiency of 100% each Example G

Blowfly larvae test / development-inhibiting effect

Test animals Lucilia cuprina larvae

Solvent: dimethyl sulfoxide

20 mg of active ingredient are dissolved in 1 ml of dimethyl sulfoxide, lower concentrations are made by diluting with distilled water.

About 20 Lucilia cuprina larvae are placed in a test tube which contains approx. 1 cm ^ horse meat and 0.5 ml of the active ingredient preparation to be tested. The effectiveness of the active ingredient preparation is determined after 24 hours and 48 hours. The test tubes are placed in beakers with a sand-covered bottom transferred After another 2 days, the test tubes are removed and the dolls are paid out

The effect of the preparation of active substance is assessed according to the number of flies hatched after 1.5 times the development time of an untreated control. 100% means that no flies have hatched, 0% means that all flies have hatched normally

In this test, the compounds of preparation examples A-9 and A-10, for example, each show a 100% action at an exemplary active ingredient concentration of 100 μg.

Example H

Test with Boophilus icroplus resistant / SP-resistant Parkhurst strain

Test animals adult drawn females

Dimethyl sulfoxide solvent

20 mg of active ingredient are dissolved in 1 ml of dimethyl sulfoxide, lower concentrations are made by diluting with the same solvent

The test is carried out in 5-fold determination. 1 μl of the solutions is injected into the abdomen, the animals are transferred to dishes and stored in an air-conditioned room. The effect is determined by the inhibition of egg laying. 100% means that no tick has laid

In this test, the compounds of Preparation Examples A-9 and A-10, for example, each show a 100% action at an exemplary active ingredient concentration of 20 μg

Claims

claims

Compounds of formula (I)

in which

Het for one of the heterocycles

stands, where

R ^{1 represents} alkyl, haloalkyl, alkoxyalkyl, alkylthioalkyl, alkoxy, alkylthio or optionally substituted cycloalkyl,

R ^{2 represents} hydrogen, halogen, cyano, nitro, thiocyanato, alkoxycarbonyl, alkenyloxycarbonyl, alkylthio, haloalkylthio, alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, haloalkylsulfonyl or thiocarbamoyl or

R ¹ and R ² together with the carbon atoms to which they are attached represent an optionally substituted saturated or unsaturated 5- or 6-membered carbocyclic ring,

R ³ for hydrogen, alkyl, haloalkyl, alkoxyalkyl, alkylcarbonyl, alkoxycarbonyl, alkenyloxycarbonyl, alkylsulfonyl, in each case if appropriate substituted arylcarbonyl, aryloxycarbonyl, arylsulfonyl or arylalkyl or optionally substituted cycloalkyl,

R ⁴ and R ⁵ independently of one another represent hydrogen or the radicals -COR ⁶ , -COOR ⁷ and -SO ₂ R ⁸ , where

R ⁶ , R ⁷ and R ⁸ independently of one another are alkyl, haloalkyl, alkoxyalkyl, alkylthioalkyl, alkylcarbonyloxyalkyl, alkoxycarbonylalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, in each case optionally substituted cycloalkyl, cycloalkylalkyl, cycloalkoxyalkyl or cycloalkylthioalkyl; each optionally substituted aryl, arylalkyl, aryloxyalkyl or arylthioalkyl or represent an optionally substituted heterocycle,

X ¹ and X ² independently of one another represent halogen, nitro, cyano, alkyl, alkoxy or haloalkyl,

m and n independently of one another represent 0, 1, 2 or 3 and

Y stands for optionally substituted alkylene, alkenylene or alkyleneoxy

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

Het for the heterocycles

stands, where R ¹ for C _j -C ₄ alkyl, CC ^ haloalkyl having 1 to 5 identical or different halogen atoms, such as fluorine, chlorine and bromine atoms, C ₁ -C ₄ alkoxy-C ₁ -C ₄ alkyl, C ₁ -C ₄ -alkylthio-C ₁ -C ₄ - alkyl, C ₁ -C - alkoxy, C - C alkylthio or optionally monosubstituted to trisubstituted by identical or different C _j -C ₄ - alkyl or halogen-substituted C ₃ -C ₆ Cycloalkyl,

R ² is hydrogen, halogen, cyano, nitro, thiocyanato, C _j -C ₄ - alkoxy-carbonyl, C ₂ -C alkenyloxy-carbonyl, Cι-C ₄ alkyl thio, C ₁ -C ₄ -halogenoalkylthio having 1 up to 5 identical or different halogen atoms, such as fluorine or chlorine atoms, Cγ-C ₄ alkylsulfinyl, C ₁ -C ₄ haloalkylsulfinyl with 1 to 5 identical or different halogen atoms, such as fluorine or chlorine atoms, CC ₄ - alkylsulfonyl, Cj-C ₄ -haloalkylsulfonyl with 1 to 5 identical or different halogen atoms, such as fluorine or chlorine atoms or for thiocarbamoyl; or

R ¹ and R ² together with the carbon atoms to which they are attached, for an optionally mono- to trisubstituted, identically or differently substituted carbocyclic 5- or 6-membered ring, the substituents being halogen, C _j -C ₄ -alkyl, Cι -C ₄ - haloalkyl, -CC ₄ - alkoxy, C _j -C ₄ haloalkoxy, nitro and cyano come into question.

for hydrogen, Cp -alkyl, C ₁ -C ₄ -haloalkyl having 1 to 5 identical or different halogen atoms, such as fluorine or chlorine atoms, C

C -alkoxy-C _r C ₄ -alkyl, C _r C ₄ -alkyl-carbonyl, C _r C -alkoxy-carb-onyl, C ₂ -C ₄ -alkenyloxy-carbonyl, CC ₄ - alkylsulfonyl, each optionally simple to trisubstituted by identical or different in the phenyl ring substituted phenylcarbonyl, phenyloxycarbonyl, phenylsulfonyl or benzyl, suitable substituents being in each case halogen, nitro, cyano, C _j -C ₄ - same or alkyl, CC ₂ haloalkyl having 1 to 5 different Halogen atoms, such as fluorine or chlorine atoms, CC ^ alkoxy, CC - alkylthio, -C-C ₂ haloalkoxy with 1 to 5 identical or different halogen atoms, such as fluorine or chlorine atoms or C _j -C ₂ haloalkylthio with 1 to 5 the same or different halogen atoms, such as fluorine or chlorine atoms, or represents C ₃ -C _(5- cycloalkyl) which is optionally monosubstituted to triple, identical or different, by C ₁ -C ₄ -alkyl or halogen.

R ⁴ and R ⁵ independently of one another represent hydrogen or the radicals -COR ⁶ , -COOR ⁷ or -SO ₂ R ⁸ , where

R ⁶ , R ⁷ and R ⁸ independently of one another for C _j -C ₈ alkyl, C _r C ₈ haloalkyl having 1 to 5 identical or different halogen atoms, such as fluorine, chlorine or bromine atoms, C 1 -C 4 alkoxy -C _j - C ₈ -alkyl, C _r C ₄ -alkylthio-C _r C ₈ -alkyl, C _r C ₄ -alkylcarbonyl-oxy-Cι-C ₈ -alkyl, C ₁ -C -alkoxycarbonyl-C ₁ -C ₈ alkyl; C ₂ -C ₈ alkenyl, C ₂ -C haloalkenyl having 1 to 5 identical or different halogen atoms, such as fluorine or chlorine atoms; C ₂ -C ₈ alkynyl, C ₂ -C ₈ haloalkynyl having 1 to 5 identical or different halogen atoms, such as fluorine or chlorine atoms; for C ₃ -C ₆ -cycloalkyl, C ₃ -C ₆ -cycloalkyl-C ₁ -C ₄ -alkyl, C ₃ - C ₆ -cycloalkyloxy- which are each mono- to quintuple (preferably single to triple), identical or differently substituted in the ring C _j -C ₄ alkyl or C ₃ -C ₆ cycloalkylthio-C ₁ -

C ₄ alkyl, said substituents in each case halogen, Cj-C ₄ - alkyl, C ₁ -C ₄ haloalkyl same with or different 1 to 5 halogen atoms such as fluorine or chlorine atoms, _C] -C - alkoxy, Cι-C ₄ -haloalkoxy with 1 to 5 identical or different halogen atoms, such as fluorine or chlorine atoms, C ₂ -

C ₄ alkenyl, C ₂ -C ₄ haloalkenyl having 1 to 5 identical or different halogen atoms, such as fluorine or chlorine atoms, nitro or cyano, are suitable, optionally monosubstituted in each case to five times (preferably one to three times), the same or different in the ring substituted phenyl, phenyl-C C alkyl, phenoxy-C _j -C alkyl or _{phenylthio-Cι-C4} alkyl, wherein said substituents in each case Halogen, nitro, cyano, C 1 -C ₄ -alkyl, C 1 -C ₄ -haloalkyl

1 to 5 identical or different halogen atoms, such as fluorine or chlorine atoms, C ₁ -C ₄ alkoxy, Cι-C ₄ haloalkoxy with 1 to 5 identical or different halogen atoms, such as fluorine or chlorine atoms, C] -C ₄ - alkylthio, C ₁ - C ₄ haloalkylthio having 1 to 5 identical or different halogen atoms, such as

Fluorine or chlorine atoms, C ₂ -C ₄ alkenyl, C ₂ -C ₄ haloalkenyl with 1 to 5 identical or different halogen atoms, such as fluorine or chlorine atoms, C ₁ -C ₄ alkoxycarbonyl or C ₁ -C ₄ -Alkylcarbonyloxy come into question, or for an optionally mono- to trisubstituted, identically or differently substituted 5- or 6-membered heterocycle with 1 to 3 heteroatoms, preferably from the series nitrogen, sulfur, and oxygen, which optionally also contain CO groups as ring members may contain. For example:

NI-N. NN. NN _\ NN _/ - ₌ r = \ r = os NN ^x _N _y ^N ^ N - ' each as a substituent

Halogen, nitro, cyano, C _r C ₄ alkyl, C _r C alkoxy, C _] -C ₄ -

Alkylthio, -CC ₄ -HalogenaIkyl, C -haloalkoxy and CC ₄ -haloalkylthio come into question. In addition, suitable heterocycles on the ring nitrogen atom can optionally be substituted by a radical Z, where

Z for C _j -C ₄ alkyl (such as in particular methyl or ethyl), C 1 -C ₄ alkylcarbonyl (such as in particular methylcarbonyl or ethylcarbonyl), or for optionally single or double, identical or different by C _] -C ₄ alkyl ( such as, in particular, methyl or ethyl) halogen (such as, in particular, fluorine or chlorine), C ₁ -C ₄ haloalkyl (such as, in particular, trifluoromethyl), C _j -C ₄ alkoxy

(such as especially methoxy), and C C -haloalkoxy (such as especially trifluoromethoxy) substituted phenylsulfonyl

Suitable heterocycles are to be understood as meaning nitrogen-containing heterocycles in which at least one ring nitrogen has no double bond and is therefore available for substitution

X ¹ and X ² are each independently fluorine, chlorine, bromine, nitro, cyano, ~ C ₄ alkyl, C ₁ -C ₄ alkoxy or C _j ^ -haloalkyl having 1 to 5 identical or different halogen atoms, such as fluorine or chlorine atoms

m and n are independently 0, 1 or 2 Y for C _r C ₆ -alkylene, C _r C ₆ -hydroxyalkylene, C _r C ₄ -alkoxy-C _r C ₆ -alkylene, C ₁ -C ₄ -alkylcarbonyloxy-C ₁ -C ₆ -alkylene, cyano-CC _ß alkyl, C ₁ -C ₄ haloalkylene with 1 to 5 identical or different halogen atoms, such as fluorine or chlorine atoms; C ₃ -C ₆ -cycloalkyl-C ₁ -C ₄ -alkylene, optionally monosubstituted to triple, identical or different, by fluorine, chlorine or methyl, represents C ₂ -C ₄ -alkenylene or C ^ ₄ -alkyleneoxy

Halogen for F, Cl, Br, I, in particular for F, Cl, Br and particularly emphasized for F and Cl.

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

Het for one of the heterocycles

stands, where

R ¹ for methyl, ethyl. n- or i-propyl, n-, i-, s- or t-butyl, CH ₂ C1, CH ₂ Br, CHC1CH ₃ , methoxy, ethoxy, methoxymethyl, ethoxymethyl; Methylthiomethyl, methylthio or cyclopropyl.

R ^{2 represents} hydrogen, chlorine, bromine, cyano, nitro, thiocyanato, methoxycarbonyl, ethoxycarbonyl, i-propoxycarbonyl, n-prop-oxycarbonyl; Allyloxycarbonyl, methylthio, methylsulfinyl, methylsulfonyl or CSNH ₂ , or

R ¹ and R ² together with the carbon atoms to which they are attached, for one optionally single or double, the same or different substituted carbocyclic 5- or 6-membered ring, where fluorine, chlorine, methyl, ethyl, methoxy, trifluoromethoxy, nitro and cyano are suitable as substituents.

R ^{3 is} hydrogen, methyl, ethyl, n- or i-propyl, methoxymethyl, ethoxymethyl, n-propoxymethyl, n-butoxymethyl; Methylcarbonyl, methoxycarbonyl, ethoxycarbonyl, i-propoxycarbonyl, allyloxycarbonyl, methylsulfonyl, each optionally mono- or disubstituted, identically or differently, in the phenyl ring by phenylcarbonyl, phenoxycarbonyl or benzyl substituted by fluorine, chlorine, methyl or trifluoromethyl, or represents cyclopropyl.

R ⁴ and R ⁵ independently of one another represent hydrogen or the radicals -COR ⁶ , -COOR ⁷ or -SO ₂ R ⁸ , where

R ⁶ , R ⁷ and R ⁸ independently of one another for -CC ₈ alkyl, CpC ^ haloalkyl with 1 to 5 identical or different halogen atoms, such as fluorine, chlorine or bromine atoms, C ₁ -C ₂ alkoxy-C ₁ - C ₄ -alkyl, C ₁ -C ₂ -alkylthio-C ₁ -C ₄ -alkyl, C _r C ₄ -alkylcarbonyl-oxy-C C -alkyl, Cι-C ₂ -alkoxycarbonyl-C _j -C ₄ - alkyl, C ₂ -C alkenyl, C ₂ -C ₄ haloalkenyl with 1 to 5 identical or different halogen atoms, such as fluorine or chlorine atoms, C ₂ -C ₄ alkynyl, C ₂ -C ₄ haloalkynyl with 1 to 5 same or different halogen atoms, such as fluorine or chlorine atoms, for each optionally mono- to trisubstituted, identically or differently, C ₃ -C ₆ -cycloalkyl, C ₃ -C ₆ -cycloalkyl-C _r C ₂ -alkyl, C ₃ - C ₆ -cycloalkyloxy-C _r C ₂ -alkyl and C ₃ -C ₆ -cycloalkylthio-C ₁ -C ₂ -alkyl, where as substituents halogen, CC-alkyl, C ₁ -C ₂ -haloalkyl with 1 to 5 identical or different halogen atoms, such as fluorine or chlorine atoms, CC ^ alkoxy, Cι-C ₂ -Halogenalkoxy with 1 to 5 identical or different halogen atoms, such as fluorine or Chlorine atoms, C ₂ -C ₄ alkenyl, C ₂ -C ₄ haloalkenyl with 1 to 5 identical or different halogen atoms, such as fluorine or chlorine atoms, nitro or cyano come into question, for each optionally one to three times, identical or different in Ring substituted phenyl, phenyl-C ₁ -C ₂ alkyl,

Phenoxy-Cι-C ₂ alkyl or phenylthio-Cι-C ₂ alkyl, suitable substituents being in each case halogen, nitro, cyano, C ₂ alkyl, C _j - C same ₂ haloalkyl having 1 to 5 or different halogen atoms , such as fluorine or chlorine atoms, CC ₂ alkoxy, Cγ- C ₄ haloalkoxy with 1 to 5 identical or different

Halogen atoms, such as fluorine or chlorine atoms, C _] -C ₂ alkylthio, C _j -C ₂ haloalkylthio with 1 to 5 identical or different halogen atoms, such as fluorine or chlorine atoms, C ₂ -C ₄ alkenyl, C ₂ -C haloalkenyl having 1 to 5 identical or different halogen atoms comparable, such as fluorine or chlorine atoms, and C _j ^ -C alkoxycarbonyl, or C ₁ -C ₂ alkylcarbonyloxy or come in question for the following, which is optionally mono- to trisubstituted by identical or different substituted heterocycles:

N * N each as a substituent Fluorine, chlorine, bromine, nitro, cyano; Methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl; Methoxy, ethoxy, n- or i-propoxy; Methylthio; -CF ₃ , -CHF ₂ , -OCF ₃ and -OCHF ₂ are possible,

in which

Z for CC ₄ -alkyl, such as in particular methyl or ethyl;

-C-C ₄ alkylcarbonyl, such as in particular methylcarbonyl or ethylcarbonyl; or for optionally single or double, identical or different by CC ₄ alkyl, such as in particular methyl or ethyl; Halogen, such as in particular fluorine or chlorine; C ₁ -C ₄ haloalkyl, such as in particular trifluoromethyl; CC - alkoxy, such as especially methoxy; and -CC ₄ haloalkoxy, such as in particular trifluoromethoxy substituted phenylsulfonyl.

X ¹ and X ^{2 are} independently fluorine, chlorine, nitro, cyano, methyl, methoxy or trifluoromethyl.

m and n independently of one another represent 0, 1 or 2, in particular 0 or 1.

Y for one of the radicals -CH ₂ -, -CH (CH ₃ ) -, -CH (C ₂ H ₅ ) -, -CH (nC ₃ H ₇ ) -,

-CH (iC ₃ H ₇ ) -, -CH ₂ CH ₂ -, -CH (OH) -, -CH (OCH ₃ ) -,

-CH (O-CO-CH ₃ ) -, -CH (CN) -, -CHF-, -CHC1-, -CH (- <3) -, -CH = CH- or -CH ₂ O-.

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

Het for one of the heterocycles

stands.

R ^{1 is} methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl; CH ₂ C1, CH ₂ Br, methoxy, ethoxy, methylthio or cyclopropyl.

R ^{2 represents} hydrogen, chlorine, bromine, cyano, nitro, methoxycarbonyl, ethoxycarbonyl, methylthio, methylsulfinyl or methylsulfonyl; or

R ¹ and R ² together with the carbon atoms to which they are attached represent a 6-membered carbocyclic ring which is optionally mono- or disubstituted, identically or differently, by fluorine, chlorine, methyl, nitro or cyano.

R ^{3 represents} hydrogen, methyl, ethyl, methoxymethyl, ethoxymethyl, methylcarbonyl, methoxycarbonyl, ethoxycarbonyl, i-propoxycarbonyl, allyloxycarbonyl or phenoxycarbonyl.

R ⁴ and R ⁵ independently of one another represent hydrogen or the radicals -COR ⁶ , -COOR ⁷ or -SO ₂ R ⁸ , where

R ⁶ , R ⁷ and R ⁸ independently of one another are methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, n-pentyl, 2,2-dimethylpropyl, n-

Hexyl, n-heptyl, n-octyl; for 2-propenyl, 1-propenyl, 2-propynyl; for chloromethyl, 2-chloroethyl, trifluoromethyl, 2,2,2-trifluoroethyl; for methoxymethyl, methoxyethyl, ethoxymethyl; for each optionally single to triple, identical or different, by methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, fluorine, chlorine, bromine or 2,2-dichlorovinyl substituted cyclopropyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclopentylmethyl or cyclohexylmethyl, each in each case optionally up to three times, identically or differently by fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, methoxy, ethoxy, methylthio, trifluoromethyl, Trifluoromethoxy, trifluoromethylthio, methoxycarbonyl, ethoxycarbonyl or methylcarbonyloxy substituted phenyl or benzyl, or for a heterocycle which is in each case monosubstituted to triple, identical or different, from the series 1-furyl, 2-furyl, 1-thienyl, 2-thienyl, l , 3-oxazol-2-yl; 1,3-oxazol-4-yl, 1,3-thiazol-2-yl, 1,3-thiazol-4-yl, 1,2-oxazol-3-yl, 1,2-oxazol-4-yl, 1, 2-oxazol-5-yl, l, 2-thiazol-3-yl, 1,2-thiazol-4-yl, l,

2-thiazol-5-yl,

3-pyrazolyl,

4-pyrazolyl,

5- pyrazolyl, 2-pyridyl, 3-pyridyl and 4-pyridyl, where fluorine, chlorine, bromine, nitro, cyano, methyl, ethyl, methoxy, ethoxy or trifluoromethyl are suitable as substituents

X ¹ and X ^{2 are} independently fluorine, chlorine, cyano, methyl or trifluoromethyl

m and n independently of one another represent 0 or 1, in particular 0

Y represents -CH ₂ -, -CH (CH ₃ ) - or -CH ₂ O-, in particular -CH ₂ - or -CH (CH ₃ ) -

A process for the preparation of compounds of formula (I) according to claim 1, characterized in that a) nitro derivatives of the formula (II)

in which

Het, R ³ , X ¹ , X ² , Y, m and n have the meaning given in claim 1,

with base metals in acidic solution or by catalytic hydrogenation, optionally in the presence of a diluent and

b) optionally the amino derivatives of the formula (1-1) thus obtained

in which

Het, R ³ , X ¹ , X ² , Y, m and n have the meaning given in claim 1,

with compounds of the formula (III)

4-1 ^{G "R} (in), in which

R ⁴ " ^{1 stands} for the meanings of R ⁴ , except hydrogen, and

G represents a leaving group,

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

or

c) amino heterocycles of the formula (IV)

Het - H

N ^' (IV),

R °

in which

Het and R ^{3 have} the meaning given in claim 1,

with compounds of formula (V)

in which

G, R ⁴ " ¹ , R ⁵ , X ¹ , X ² , Y, m and n have the meaning given above and if appropriate in the presence of a base and if appropriate in the presence of a diluent.

6. Compounds of formula (V)

in which

G, R ⁵ , X ¹ , X ² , Y, m and n have the meaning given in claim 1 and

R ⁴ " ^{1 has} the meaning of R ⁴ given in claim 1 with the exception of hydrogen.

7. Compounds of the formula (VI)

in which

R ⁵ , X ¹ , X ² , Y, m and n have the meaning given in claim 1 and

R ^{4_1 has} the meaning of R ⁴ given in claim 1 with the exception of

Has hydrogen. Pesticides or fungicides, characterized in that they contain a compound of the formula (I) according to Claim 1

Use of compounds of the formula (I) according to Claim 1 for combating pests and fungi

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

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