AU8111198A - Substituted aminoheterocyclylamides - Google Patents

Description

Substituted aminoheterocyclylamides The invention relates to novel substituted aminoheterocyclylamides, to processes and 5 intermediates for their preparation and to 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, has insecticidal properties 10 (cf., for example, WO 95/31 448, DE-A-9 542 372; WO 93/04 580, WO 96/08 475, DE-A-4 434 637; WO 97/26 251 and WO 95/18 795). However, the activity and the activity spectrum of these compounds are, in particular at low application rates and concentrations, not always entirely satisfactory. 15 This invention, accordingly, provides novel substituted aminoheterocyclylamides of the formula (I)

NR

4

R

6 Het - CO OR4 N

R

3 X2m 20 in which Het represents one of the heterocycles N- N R R 2 ~ R R o r R .. w h e re

R

1 represents alkyl, halogenoalkyl, alkoxyalkyl, alkylthioalkyl, alkoxy, 25 alkylthio or optionally substituted cycloalkyl, -2

R

2 represents hydrogen, halogen, cyano, nitro, thiocyanato, alkoxy carbonyl, alkenyloxycarbonyl, alkylthio, halogenoalkylthio, alkylsulphinyl, halogenoalkylsulphinyl, alkylsulphonyl, halogenoalkylsulphonyl or thiocarbamoyl or 5 RI 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, halogenoalkyl, alkoxyalkyl, alkylcarbonyl, alkoxy 10 carbonyl, alkenyloxycarbonyl, alkylsulphonyl, in each case optionally substituted arylcarbonyl, aryloxycarbonyl, arylsulphonyl or arylalkyl or optionally substituted cycloalkyl,

R

4 and R 5 independently of one another each represent hydrogen or represent the 15 radicals -COR 6 , -COOR 7 and -SO 2

R

8 where

R

6 , R 7 and R 8 independently of one another each represent alkyl, halogeno alkyl, alkoxyalkyl, alkylthioalkyl, alkylcarbonyloxyalkyl, alkoxycarbonylalkyl; alkenyl, halogenoalkenyl; alkinyl, 20 halogenoalkinyl; in each case optionally substituted cycloalkyl, cycloalkylalkyl, cycloalkoxyalkyl or cycloalkylthioalkyl; in each case optionally substituted aryl, arylalkyl, aryloxyalkyl or arylthioalkyl or represent an optionally substituted heterocycle, 25 XI and X 2 independently of one another each represent halogen, nitro, cyano, alkyl, alkoxy or halogenoalkyl, m and n independently of one another each represent 0, 1, 2 or 3 and 30 Y represents in each case optionally substituted alkylene, alkenylene or alkenylenoxy, -3 and halogen represents F, Cl, Br, I, in particular F, Cl, Br and particularly preferably F or Cl. 5 Furthermore, it has been found that the substituted aminoheterocyclylamides of the formula (I) are obtained when a) nitro derivatives of the formula (11) 10 pN0 2 Het. CO O OQ(I R 3 Xm in which Het, R 3 , XI, X 2 , Y, m and n are each as defined above, 15 are reduced with base metals in acidic solution or by catalytic hydrogenation, if appropriate in the presence of a diluent, and -3 and halogen represents F, Cl, Br, I, in particular F, Cl, Br and particularly preferably F or Cl. 5 Furthermore, it has been found that the substituted aminoheterocyclylamides of the formula (I) are obtained when a) nitro derivatives of the formula (II) 10

HOO

2 in which Het, R 3 , XI, X 2 , Y, m and n are each as defined above, 15 are reduced with base metals in acidic solution or by catalytic hydrogenation, if appropriate in the presence of a diluent, and b) the resulting amino derivatives of the formula (I-1) 20 HCNH2 N 1 in which Het, R 3 , XI, X 2 , Y, m and n are each as defined above, 25 are, if appropriate, reacted with compounds of the formula (II) -4 G - R"'(I) in which 5

R

4

-

1 has the meanings of R 4 , except for hydrogen, and G represents a leaving group, for example halogen (in particular chlorine), imidazolyl, benzimidazolyl, 1,2,4-triazolyl, pyrazolyl or 10 benzotriazolyl, if appropriate in the presence of a base and if appropriate in the presence of a diluent; 15 or c) aminoheterocycles of the formula (IV) Hets y H N (IV),

R

3 20 in which Het and R 3 are each as defined above, are reacted with compounds of the formula (V) 25 NR4 1

R

5 G 2(V), in which -5 G, R 4

-

1 , R 5 , X 1 , X 2 , Y, m and n are each as defined above, if appropriate in the presence of a base and if appropriate in the presence of a 5 diluent. Finally, it has been found that the novel substituted aminoheterocyclylamides of the formula (I) have strongly pronounced biological properties and are primarily suitable for use as fungicides and for controlling animal pests, in particular insects, arachnids 10 and nematodes, encountered in agriculture, in forests, in the protection of stored products and materials and in the hygiene sector. The formula (I) provides a general definition of the substituted aminoheterocyclylamides according to the invention. 15 Preferred substituents or ranges of the radicals listed in the formulae mentioned hereinabove and hereinbelow are illustrated below. Het preferably represents the heterocycles 20 / (N R N R« N 'R2 R2, NR o RN RI preferably represents CI-C 4 -alkyl, CI-C 4 -halogenoalkyl having 1 to 5 identical or different halogen atoms, such as fluorine, chlorine and 25 bromine atoms, CI-C 4 -alkoxy-CI-C 4 -alkyl, CI-C 4 -alkylthio-Ci-C 4 alkyl, CI-C 4 -alkoxy, CI-C 4 -alkylthio or represents C 3

-C

6 -cycloalkyl which is optionally mono- to trisubstituted by identical or different substituents from the group consisting of C 1

-C

4 -alkyl and halogen.

-6

R

2 preferably represents hydrogen, halogen, cyano, nitro, thiocyanato, C 1 C 4 -alkoxy-carbonyl, C 2

-C

4 -alkenyloxy-carbonyl, C 1

-C

4 -alkylthio, C 1 C 4 -halogenoalkylthio having 1 to 5 identical or different halogen atoms, such as fluorine or chlorine atoms, C 1

-C

4 -alkylsulphinyl, C 1 5 C 4 -halogenoalkylsulphinyl having 1 to 5 identical or different halogen atoms, such as fluorine or chlorine atoms, C 1

-C

4 -alkylsulphonyl, C 1 C 4 -halogenoalkylsulphonyl having 1 to 5 identical or different halogen atoms, such as fluorine or chlorime atoms, or represents thiocarbamoyl; or 10

R

1 and R 2 preferably together with the carbon atoms to which they are attached represent a carbocyctic 5- or 6-membered ring which is optionally mono- to trisubstituted by identical or different substituents, suitable substituents being halogen, C I-C 4 -alkyl, CI-C 4 15 halogenoalkyl, C I-C 4 -alkoxy, C 1

-C

4 -halogenoalkoxy, nitro and cyano.

R

3 preferably represents hydrogen, CI-C 4 -alkyl, CI-C 4 -halogenoalkyl having 1 to 5 identical or different halogen atoms, such as fluorine or chlorine atoms,

C

1

-C

4 -alkoxy-CI-C 4 -alkyl, C 1

-C

4 -alkyl-carbonyl, C 1

-C

4 -alkoxy-carbonyl, 20 C 2

-C

4 -alkenyloxy-carbonyl, C I-C 4 -alkylsulphonyl, represents phenylcarbonyl, phenyloxycarbonyl, phenylsulphonyl or benzyl, each of which is optionally mono- to trisubstituted in the phenyl ring by identical or different substituents, suitable substituents being in each case halogen, nitro, cyano, CI-C 4 -alkyl, CI-C 2 -halogenoalkyl having 1 to 5 identical or different 25 halogen atoms, such as fluorine or chlorine atoms, CI-C 4 -alkoxy, C 1

-C

4 alkylthio, CI-C 2 -halogenoalkoxy having 1 to 5 identical or different halogen atoms, such as fluorine or chorine atoms, or CI-C 2 -halogenoalkylthio having 1 to 5 identical or different halogen atoms, such as fluorine or chlorine atoms, or represents C 3

-C

6 -cycloalkyl which is optionally mono- to trisubstituted by 30 identical or different substituents from the group consisting of CI-C 4 -alkyl and halogen.

-7

R

4 and R 5 preferably independently of one another each represent hydrogen or represent the radicals -COR 6 , -COOR 7 or -S0 2

R

8 where

R

6 , R 7 and R 8 preferably independently of one another each represent CI-C 8 5 alkyl, CI-C 8 -halogenoalkyl having 1 to 5 identical or different halogen atoms, such as fluorine, chlorine or bromine atoms CI-C 4 -alkoxy-C 1 C 8 -alkyl, C 1

-C

4 -alkylthio-C -C 8 -alkyl, C 1

-C

4 -alkylcarbonyloxy-C Cg-alkyl, Ci-C 4 -alkoxycarbonyl-C-Cg-alkyl;

C

2

-C

8 -alkenyl, C 2

-C

8 halogenoalkenyl having 1 to 5 identical or different halogen atoms, 10 such as fluorine or chlorine atoms; C 2

-C

8 -alkinyl, C 2

-C

8 halogenoalkinyl having 1 to 5 identical or different halogen atoms, such as fluorine or chlorine atoms; represent C 3

-C

6 -cycloalkyl,

C

3

-C

6 -cycloalkyl-CI-C 4 -alkyl, C 3

-C

6 cycloalkyloxy-C 1

-C

4 -alkyl or C 3

-C

6 -cycloalkylthio-C -C 4 -alkyl, each 15 of which is optionally mono- to pentasubstituted (preferably mono- to trisubstituted) in the ring by identical or different substituents, suitable substituents being in each case halogen, Ci-C 4 -alkyl, CI-C 4 halogenoalkyl having I to 5 identical or different halogen atoms, such as fluorine or chlorine atoms, CI-C 4 -alkoxy, C 1

-C

4 -halogenoalkoxy 20 having 1 to 5 identical or different halogen atoms, such as fluorine or chlorine atoms, C 2

-C

4 -alkenyl, C 2

-C

4 -halogenoalkenyl having 1 to 5 identical or different halogen atoms, such as fluorine or chlorine atoms, nitro or cyano, represent phenyl, phenyl-Ci-C 4 -alkyl, phenoxy-C-C 4 -alkyl or 25 phenylthio-C 1

-C

4 -alkyl, each of which is optionally mono- to pentasubstituted (preferably mono- to trisubstituted) in the ring by identical or different substituents, possible substituents being in each case halogen, nitro, cyano, CI-C 4 -alkyl, CI-C 4 -halogenoalkyl having I to 5 identical or different halogen atoms, such as fluorine or chlorine 30 atoms, CI-C 4 -alkoxy, C 1

-C

4 -halogenoalkoxy having 1 to 5 identical or different halogen atoms, such as fluorine or chlorine atoms, CI-C 4 alkylthio, C 1

-C

4 -halogenoalkylthio having 1 to 5 identical or different -8 halogen atoms, such as fluorine or chlorine atoms, C 2

-C

4 -alkenyl, C 2 C 4 -halogenoalkenyl having 1 to 5 identical or different halogen atoms, such as fluorine or chlorine atoms, CI-C 4 -alkoxycarbonyl or Ci-C4 alkylcarbonyloxy, 5 or represent a 5- or 6-membered heterocycle having I to 3 heteroatoms, preferably from the group consisting of nitrogen, sulphur and oxygen, which may optionally also contain CO groups as ring members, and which is optionally mono- to trisubstituted by identical or different substituents. Examples include: 0 S N N 0 S N N H I H I 10 Z Z RN -\\N N ' N 2 4 7 FN\ k N N N N' o S N N 0 S N N H I H z z N-N N-N N-N N-N NCN N, H NN z o S 0 NH N N N'N NN N N N N H N N H NNN - , suitable substituents being in each case N 15 halogen, nitro, cyano, C 1

-C

4 -alkyl, C 1

-C

4 -alkoxy, C 1

-C

4 -alkylthio,

C

1

-C

4 -halogenoalkyl, C 1

-C

4 -halogenoalkoxy and CI-C 4 halogenoalkylthio. Additionally, suitable heterocycles may optionally be substituted at the ring nitrogen atom by a radical Z where 20 Z represents C I-C 4 -alkyl (such as, in particular methyl or ethyl),

C

1

-C

4 -alkylcarbonyl (such as, in particular, methylcarbonyl or ethylcarbonyl), or represents phenylsulphonyl which is optionally mono- or disubstituted by identical or different substituents from the group consisting of C I-C 4 -alkyl (such as, -9 in particular, methyl or ethyl), halogen (such as, in particular, fluorine or chlorine), C 1

-C

4 -halogenoalkyl (such as, in particular, trifluoromethyl), CI-C 4 -alkoxy (such as, in particular, methoxy) and C 1

-C

4 -halogenoalkoxy (such as, in 5 particular, trifluoromethoxy). Suitable heterocycles are nitrogen-containing heterocycles in which at least one ring nitrogen does not carry a double bond and is consequently available for substitution. 10 XI and X 2 independently of one another each preferably represent fluorine, chlorine, bromine, nitro, cyano, Ci-C 4 -alkyl, CI-C 4 -alkoxy or C 1

-C

4 -halogenoalkyl having 1 to 5 identical or different halogen atoms, such as fluorine or chlorine atoms. 15 m and n independently of one another each preferably represent 0, 1 or 2. Y preferably represents C 1

-C

6 -alkylene, Cl-C 6 -hydroxyalkylene, Ci-C 4 -alkoxy

C

1

-C

6 -alkylene, Ci-C 4 -alkylcarbonyloxy-C-C 6 -alkylene, cyano-C-C 6 alkylene, C 1

-C

4 -halogenoalkylene having 1 to 5 identical or different halogen 20 atoms, such as fluorine or chlorine atoms, C 3

-C

6 -cycloalkyl-C -C 4 -alkylene which is optionally mono- to trisubstituted by identical or different substituents from the group consisting of fluorine, chlorine and methyl, represents C 2

-C

4 -alkenylene or CI-C 4 -alkylenoxy. 25 Halogen preferably represents F, Cl, Br, I, in particular F, Cl, Br, particular emphasis being placed on F and Cl. Het particularly preferably represents one of the heterocycles 3 R R 30 S N R N~R1 - 10 RI particularly preferably represents methyl, ethyl, n- or i-propyl, n-, i-, s or t-butyl; CH 2 CI, CH 2 Br, CHClCH 3 ; methoxy, ethoxy, methoxymethyl, ethoxymethyl; methylthiomethyl, methylthio or 5 cyclopropyl.

R

2 particularly preferable represents hydrogen, chlorine, bromine, cyano, nitro, thiocyanato; methoxycarbonyl, ethoxycarbonyl, i-propoxy carbonyl, n-propoxycarbonyl; allyloxycarbonyl; methylthio, 10 methylsulphinyl, methylsulphonyl or CSNH 2 ; or

R

1 and R 2 together with the carbon atoms to which they are attached particularly preferably represent a carbocyclic 5- or 6-membered ring which is optionally mono- or disubstituted by identical or different 15 substituents, suitable substituents being fluorine, chlorine, methyl, ethyl, methoxy, trifluoromethoxy, nitro and cyano.

R

3 particularly preferable represents hydrogen, methyl, ethyl, n- or i-propyl; methoxymethyl, ethoxymethyl, n-propoxymethyl, n-butoxymethyl; 20 methylcarbonyl, methoxycarbonyl, ethoxycarbonyl, i-propoxycarbonyl, allyloxycarbonyl, methylsulphonyl; phenylcarbonyl, phenoxycarbonyl or benzyl, each of which is optionally mono- or disubstituted in the phenyl ring by identical or different substituents from the group consisting of fluorine, chlorine, methyl and trifluoromethyl; or represents cyclopropyl. 25

R

4 and R 5 independently of one another each particularly preferably represent hydrogen or represent the radicals -COR 6 , -COOR 7 or -S0 2

R

8 , where

R

6 , R 7 and R 8 independently of one another each particularly preferably 30 represent Ci-C 8 -alkyl, CI-C 4 -halogenoalkyl having 1 to 5 identical or different halogen atoms, such as fluorine, chlorine or bromine atoms, C I-C 2 -alkoxy-C I-C 4 -alkyl, C 1

-C

2 -alkylthio-C I-C 4 -alkyl, CI-C 4

-

-11 alkylcarbonyloxy-C-C 4 -alkyl, C I-C 2 -alkoxycarbonyl-C, -C 4 -alkyl;

C

2

-C

4 -alkenyl, C 2

-C

4 -halogenoalkenyl having 1 to 5 identical or different halogen atoms, such as fluorine or chlorine atoms; C 2

-C

4 alkinyl, C 2

-C

4 -halogenoalkinyl having 1 to 5 identical or different 5 halogen atoms, such as fluorine or chlorine atoms; represent

C

3

-C

6 -cycloalkyl,

C

3

-C

6 -cycloalkyl-C 1

-C

2 -alkyl, C 3

-C

6 cycloalkyloxy-Ci-C 2 -alkyl and C 3

-C

6 -cycloalkylthio-Cl-C 2 -alkyl, each of which is optionally mono- to trisubstituted in the ring by identical or different substitutents, possible substituents being in each 10 case halogen, CI-C 4 -alkyl, CI-C 2 -halogenoalkyl having 1 to 5 identical or different halogen atoms, such as fluorine or chlorine atoms, CI-C 2 -alkoxy, CI-C 2 -halogenoalkoxy having 1 to 5 identical or different halogen atoms, such as fluorine or chlorine atoms, C 2

-C

4 alkenyl, C 2

-C

4 -halogenoalkenyl having 1 to 5 identical or different 15 halogen atoms, such as fluorine or chlorine atoms, nitro or cyano, represent phenyl, phenyl-C 1

-C

2 -alkyl, phenoxy-C 1

-C

2 -alkyl or phenylthio-C 1

-C

2 -alkyl, each of which is optionally mono- to trisubstituted in the ring by identical or different substituents, possible substituents being in each case halogen, nitro, cyano, C I-C 2 -alkyt, CI 20 C2-halogenoalkyl having 1 to 5 identical or different halogen atoms, such as fluorine or chlorine atoms, CI-C 2 -alkoxy,

CI-C

4 halogenoalkoxy having 1 to 5 identical or different halogen atoms, such as fluorine or chlorine atoms, CI-C 2 -alkylthio,

CI-C

2 halogenoalkylthio having 1 to 5 identical or different halogen atoms, 25 such as fluorine or chlorine atoms, C 2

-C

4 -alkenyl, C 2

-C

4 halogenoalkenyl having 1 to 5 identical or different halogen atoms, such as fluorine or chlorine atoms, and also CI-C 2 -alkoxycarbonyl or C I-C 2 -alkylcarbonyloxy or represent the heterocycles below, which are optionally mono- to 30 trisubstituted by identical or different substituents: -12 N N N N 0 S N N H I H I Z z -N N- N- N O N N N > N, *>N \N N 0 N0' S' N N H IH I z z oN N N H I z o sO N N N N, NH N H 5

-

possible substituents being in each case N 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 -OCHF2 10 and where Z represents

CI-C

4 -alkyl, such as, in particular, methyl or ethyl; Ci-C 4 -alkylcarbonyl, such as, in particular, methylcarbonyl or ethylcarbonyl; or represents phenylsulphonyl which is 15 optionally mono- or disubstituted by identical or different substituents from the group consisting of CI-C 4 -alkyl, such as, in particular, methyl or ethyl; halogen, such as, in particular, fluorine or chlorine;

C

1

-C

4 -halogenoalkyl, such as, in particular, trifluoromethyl;

CI-C

4 -alkoxy, such as, in 20 particular, methoxy; and Ci-C4-halogenoalkoxy, such as, in particular, trifluoromethoxy. XI and X 2 independently of one another each particularly preferably represent fluorine, chlorine, nitro, cyano, methyl, methoxy or trifluoromethyl.

- 13 m and n independently of one another each particularly preferably represent 0, 1 or 2, in particular 0 or 1. 5 Y particularly preferably represents one of the radicals -CH 2 -, -CH(CH 3 )-,

-CH(C

2

H

5 )-, -CH(n-C 3

H

7 )-, -CH(i-C 3

H

7 )-, -CH 2

CH

2 -, -CH(OH)-,

-CH(OCH

3 )-, -CH(O-CO-CH 3 )-, -CH(CN)-, -CHF-, -CHCI-, -CH(-< )-, -CH=CH- or -CH 2 0-. 10 Het very particularly preferably represents one of the heterocycles R R 2 R or Ri N NN~R or N,.. S S N R N R RI very particularly preferably represents methyl, ethyl, n- or i-propyl, n-, 15 i-, s- or t-butyl; CH 2 Cl, CH 2 Br, methoxy, ethoxy, methylthio or cyclopropyl. R2 very particularly preferably represents hydrogen, chlorine, bromine, cyano, nitro, methoxycarbonyl, ethoxycarbonyl, methylthio, 20 methylsulphinyl or methylsulphonyl; or RI and R 2 together with the carbon atoms to which they are attached ver particularly preferably represent a 6-membered carbocyclic ring which is optionally mono- or disubstituted by identical or different 25 substituents from the group consisting of fluorine, chlorine, methyl, nitro and cyano.

-14 R3 very particularly preferably represents hydrogen, methyl, ethyl, methoxymethyl, ethoxymethyl, methylcarbonyl, methoxycarbonyl, ethoxycarbonyl, i-propoxycarbonyl, allyloxycarbonyl or phenoxycarbonyl. 5 R 4 and R 5 independently of one another each very particularly preferably represent hydrogen or represent the radicals -COR 6 , -COOR 7 or -S0 2

R

8 where

R

6 , R 7 and R 8 independently of one another each very particularly preferably 10 represent methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, n-pentyl, 2,2-dimethylpropyl, n-hexyl, n-heptyl, n-octyl; represent 2-propenyl, 1 -propenyl, 2-propinyl; represent chloromethyl, 2-chloroethyl, trifluoromethyl, 2,2,2 trifluoroethyl; 15 represent methoxymethyl, methoxyethyl, ethoxymethyl; represent cyclopropyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclopentylmethyl or cyclohexylmethyl, each of which is optionally mono- to trisubstituted by identical or different substituents from the group consisting of methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, 20 methoxy, ethoxy, fluorine, chlorine, bromine and 2,2-dichlorovinyl, represent phenyl or benzyl, each of which is optionally mono- to trisubstituted by identical or different substituents from the group consisting of fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, methoxy, ethoxy, methylthio, trifluoromethyl, trifluoromethoxy, 25 trifluoromethylthio, methoxycarbonyl, ethoxycarbonyl and methylcarbonyloxy, or represent a heterocycle from the group consisting of 1-firyl, 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; 1,2-oxazol-3-yl; 1,2-oxazol-4-yl; 1,2-oxazol-5-yl; 30 1,2-thiazol-3-yl; 1,2-thiazol-4-yl; 1,2-thiazol-5-yl; 3-pyrazolyl, 4 pyrazolyl, 5-pyrazolyl, 2-pyridyl, 3-pyridyl and 4-pyridyl, each of which is optionally mono- to trisubstituted by identical or different - 15 substituents, possible substituents being fluorine, chlorine, bromine, nitro, cyano, methyl, ethyl, methoxy, ethoxy or trifluoromethyl. XI and X 2 independently of one another each very particularly preferable 5 represent fluorine, chlorine, cyano, methyl or trifluoromethyl. m and n independently of one another each veny particularly preferably represent 0 or 1, in particular 0. 10 Y very particularly preferable represents -CH 2 -, -CH(CH 3 )- or -CH 2 0-, in particular represents -CH 2 - or -CH(CH 3

)-

In a preferred embodiment, one of the substituents R 4 or R 5 represents hydrogen. 15 Preferred groups of compounds according to the invention are in each case the substances of the formulae (IA) to (ID): -16 R R2 NR4 R5 Coll (IA) R3 X RX m R / ' NR 4

R

5 N NO (IB)

R

3 m N r NRR5 (IC) N R n in which R I, R 2 , R 3 , R 4 , R 5 , XI, X 2 , Y, m and n each represent the abovementioned 5 general, preferred, particularly preferred and very particularly preferred meanings.

- 17 Preferred groups of compounds according to the invention are also in each case the substances of the formulae (IA-1) to (IA-8), (IB-1) to (IB-8), (IC-1) to (IC-8) and (ID-1) to (ID-8): S N CH 2 f 0-fD - NH 2 (IA-1) R R R I Co R S 2 O CH2 O NH - CO R6 (IA-2 ) R R R R1 C O N S N CH 0 NH -COOR 7 (IA-3) 2CH R R C inwCo N S N~ CH 2( H-0 IA-4)

R

3 R1 R2 'I I Co

R

3

CH

3 R R2 CO S N CH 0/ \ NH-COR 6 (IA-6) R CH \/3 R 1R H CO N CH \ 0/// NH-COOR' (IA-7) R OH 3 R ~R 2 N, /JI N\H NH-S0 2 R 8 (IA-8) 5

R

3

CF-

3 in which - 18 RI, R 2 , R 3 , R 6 , R 7 and R 8 each represent the abovementioned general, preferred, particularly preferred and very particularly preferred meanings. N R CO Q CH

R

2 N CH 2 - 0( NH (IB-1) R RI Co R2 N CH2 O-7 NH -COR ( IB-3 ) R CO R R Co -0 / 7 2 CH 0 NH - COR ( IB-3) 3 CH R R Co R2 / O NH-SOR 8 ( IB-4) R CH

R

3 R CO 2 CH ONH-2R ( IB-5) R CH 3 i wCo

R

2 N OH -// '-NH-COR' (IB-6) R R 3 OH 0 = R Co 2 N~ CH /0 / "NH -COOR' (16-7) R R1 3 OH-C R Co 2 -0O / \ HSR 8 (IB-8) R R /H 2 in which - 19 RI, R 2 , R 3 , R 6 , R 7 and R 8 each represent the abovementioned general, preferred, particularly preferred and very particularly preferred meanings. N CH 2 0 NH 2 (IC-1) R N R1 -- </ CO N CH 2 - - \NH-C (IC-2) R N N N CH2O NH-COOR' ( IC-3)

R

3 H R CO N CH O / ' NH -SO2R ( IC-) R N RRCO N OH 0 NH2 (IC-5) R COH 3 NRH O NH -COR (- ) R C 3 N N N/\CH O NH - SO2R' ( IC-8 ) 5 R 3 OH -0 wR CH in whic - 20 R 1 , R 3 , R 6 , R 7 and R 8 each represent the abovementioned general, preferred, particularly preferred and very particularly preferred meanings. R N N

CH

2 0

NH

2 (ID-1) 13 R R

R

3 OH N SN C CH2 O \NH-COR6 (ID-3) R R I N C N N CH2 O( ID4 1 R NS N H O NH2COR (iD-5) R NR/ \ NH-COR1 (0-) N N H O /-ORID-7 R CH R NC N 'S N H O/ NH - O2R( ID-8 5 in which -21 RI, R 3 , R 6 , R 7 and R 8 each represent the abovementioned general, preferred, particularly preferred and very particularly preferred meanings. 5 The abovementioned general or preferred radical definitions or illustrations apply both to the end products and, correspondingly, to the starting materials and intermediates. These radical definitions can be combined with each other as desired, i.e. including combinations between the respective preferred ranges. 10 Preference according to the invention is given to the compounds of the formula (I) which contain a combination of the meanings listed above as being preferred (preferable). Particular preference according to the invention is given to the compounds of the 15 formula (I) which contain a combination of the meanings listed above as being particularly preferred. Very particular preference according to the invention is given to the compounds of the formula (I) which contain a combination of the meanings listed above as being 20 very particularly preferred. In the radical definitions listed above and below, hydrocarbon chains, such as alkyl or alkenyl, are in each case straight-chain or branched, as far as this is possible - also in combination with heteroatoms, such as in alkoxy or alkylthio. 25 In the abovementioned radical definitions, alkylenoxy- or -CH 2 0- are to be understood such that R 4 in the formula (I) is attached to the oxygen of the alkylenoxy or -CH 2 0- radical. 30 In addition to the Preparation Examples, the following compounds may be mentioned specifically: - 22 Table 1, NS 11 N OH 2 0 -&)\- NH-R 4 (1a) H 5 Compounds of Table 1 correspond to the general formula (1a), in which RI = C 2

H

5

R

2 = Cl R4 = as listed below:

-COCH

3 -co-&~-ci -CO0-cl

-COC

2

H

5 -C0-&OCH,

O

-COC

3

H

7 -I CI -o

-COC

3

H

7 -n -C- CH COOCH 2 CH=zCH 2

-COC

4

H

9 -n COH~i-COOCH C

-COC

4 Hq-t - C 0-co S

-COCH

2

C

4

H

9 -t Nc-C S 2 H -C0C 6

H

1 3 -n NS 2 CH -co-<c -CO- CJ-N -S0 2

C

3

H-

7 -i -23 R4 R4 R4 N- C1 -SO 2

C

3

H

7 -n -CO-J -COOCH 3 -S0 2

C

4

H

9 -n

-COCH

2 CH=CH2

-COOC

2

H

5 -S0 2

C

6

H

1 3 -n

-COCH

2 C=-CH

-COOC

3

H

7 -i - <

-COCH

2 Cl

-COOC

4 H9-n C1 C1

-COOC

4

H

9 -t

-SO

2

CH

2

CH=CH

2

-CO-

CH=CCI

2 CI CI

-COOCH

2

C

4

H

9 -t -CO r-02

CH

3 -CO-0

-COOC

6

H

1 3 -n -802a C1 Table 2 Compounds of Table 2 correspond to the general formula (la), in which 5 RI = CH 3

R

2 and R 4 = as listed in Table 1. Table 3 10 Compounds of Table 3 correspond to the general formula (Ia), in which R2 = Br

R

1 and R 4 = as listed in Table 1. Table 4 -24 Compounds of Table 4 correspond to the general formula (Ia), in which

R

2 =CN

R

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

R

2 = H 10 R 1 and R 4 = as listed in Table 1. Table 6 R CO R2 CH2 a O- a NHR 4 (b) H 15 Compounds of Table 6 correspond to the general formula (1b), in which R = C 2

H

5 or CH 3 , R 2 = Cl, Br, CN or H and R 4 = as listed in Table 1. Table 7 20 N CH 2 G O NHR4 (lb-1) H Compounds of Table 7 correspond to the general formula (Lb-1), in which R4= as listed in Table 1.

-25 Table 8 F N SCO CH2 O- -NHR 4 (Ib-2) H 5 Compounds of Table 8 correspond to the general formula (Ib-2), in which R4= as listed in Table 1. Table 9 N R CO N N

\CH

2 O NHR ( Ic) 10 H Compounds of Table 9 correspond to the general formula (Ic), in which R = C 2

H

5 R4= as listed in Table 1. 15 Table 10 Compounds of Table 10 correspond to the general formula (Ic), in which R = i-C 3

H

7 20 R4 = as listed in Table 1. Table 11 Compounds of Table 11 correspond to the general formula (Ic), in which 25 R =

CH

3 R4= as listed in Table 1.

- 26 Table 12 Compounds of Table 12 correspond to the general formula (Ic), in which R -< 5 R4 = as listed in Table 1. Table 13 RI N- CO NS N CH2 ( O N(HR 4 (Id) H 10 Compounds of Table 13 correspond to the general formula (Id), in which RI = C 2

H

5 , i-C 3

H

7 , CH 3 or and R 4 = as listed in Table 1. Using, according to process (a), for example 4 -chloro-3-methyl-5-[4-(4-nitro 15 phenoxy)]phenyl-acetylamino-isothiazole and iron powder in the presence of hydrochloric acid as starting materials, the course of the process according to the invention can be represented by the following reaction scheme:

H

3 C CI S C CH2 O NO2 H 22 H3C CI Fe/HCI || NS N CH O

NH

2 H2 20 Using, according to process (b), for example 5-[ 4 -(4-aminophenoxy)]phenyl acetylamino-4-chloro-3-methylisothiazole and pivaloyl chloride as starting materials, -27 the course of the process according to the invention can be represented by the following reaction scheme:

H

3 C CI S N C O\ /0

-NH

2 +Cf-CO-C(CH3)3 H H2-O-C base

H

3 C CI - HCI N C \ O NH-CO C(CH)A H H2 5 Using, according to process (c), for example 5-amino-4-chloro-3-ethyl-isothiazole and 4

-(

4 -t-butylcarbonylaminophenoxy)-phenylacetyl chloride as starting materials, the course of the process according to the invention can be represented by the following reaction scheme: HC CC + C--CO-C O K NH-CO-C(CH 3 ) s NH 2 2 base HAC 2 - CI H HCI O \ / 0 NH-CO-C(CH 3

)

3 10 H H Most of the nitro derivatives of the formula (II) required as starting materials for carrying out the process (a) according to the invention are 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 they can be obtained by the processes described therein. 15 The amino derivatives of the formula (I-1) required as starting materials for carrying out the process (b) according to the invention are compounds according to the invention.

- 28 The compounds of the formula (II) further to be used as starting materials in the process (b) according to the invention are generally known compounds of organic chemistry, and/or they can be obtained by generally known and customary processes. 5 Most of the aminoheterocycles of the formula (IV) required as starting materials for carrying out the process (c) according to the invention are 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. 989, 32, 1970-77; J. Prakt. Chem. 1989, 331, 369-74; Tetrahedron 1971, 2581; J. Org. Chem. 195.2, 547; J. Het. Chem. 1970, 81; J. Org. Chem. 1981, 10 2134; J. Heterocycl. Chem. 1987, 14, 1413; JP 60 109 571; EP-A 0 455 356; Chem. Ber. 1954, 87, 57; and Chem. Ber. 956, 89, 2742), and/or they can be obtained by the processes described therein. The compounds of the formula (V) furthermore to be used as starting materials in the 15 process (c) according to the invention are novel. They are obtained by activating acid derivatives of the formula (VI) NR4 1 R5 HO (V, in which 20

R

4

-

1 , R 5 , X 1 , X 2 , Y, m and n are each as defined above, in a generally known and customary manner, such as, for example, by reaction with thionyl chloride, oxalyl chloride, phosphorus oxychloride, carbonyldiimidazole and 25 similar activating reagents (cf. also general textbooks of organic chemistry). The acid derivatives of the formula (VI) are likewise novel. They are obtained by reacting aminophenoxyphenyl acid derivatives of the formula (VII) - 29 NH 2 HO Y CI O NH (VII), in which XI, X 2 , Y, m and n are each as defined above, 5 and which are known or obtainable in a generally customary manner (cf., for example, US-4 168 385) with compounds of the formula (III) 10 G-R4-1 (II), in which G and R 4

-

1 are each as defined above, 15 and, if appropriate, subsequently with compounds of the formula (IIIa)

G-R

5 -1 (IIUa), in which 20 G is as defined above and

R

5

-

1 has the meanings of R 5 , except for hydrogen, 25 in each case according to the conditions of the process (b) according to the invention. The reduction according to the process (a) described above for preparing the compounds of the formula (I) is carried out using either base metals, such as, for example, iron, tin or zinc, preferably in the presence of an acid, such as, for example, -30 hydrochloric acid or sulphuric acid; or by hydrogenation using molecular hydrogen in the presence of customary catalysts, such as, for example, platinum oxide, palladium/carbon or Raney nickel. 5 In some cases, it is advantageous to carry out the reduction according to process (a) using other customary reducing agents. Examples which may be mentioned are hydrazine, sodium hydrogen sulphide or formic acid in the presence of palladium/carbon. 10 The process (a) described above for preparing the compounds (I) is, if appropriate, carried out in the presence of a diluent. Preference is given to using alcohols, such as methanol and ethanol, and mixtures of alcohols with water. When carrying out the process (a) according to the invention, the reducing agent is 15 generally employed in excess. The reaction temperatures in the process (a) described above can be varied within a relatively wide range. In general, the process is carried out at temperatures between 0*C and 150*C, preferably between 20*C and 100*C. 20 The processes (b) and (c) described above for preparing the compounds of the formula (I) are carried out in the presence of a diluent. Suitable diluents are all customary solvents. 25 Preference is given to using optionally halogenated aliphatic or aromatic hydrocarbons, ethers or nitriles, such as, for example, cyclohexane, toluene, chlorobenzene, chloroform, dichloromethane, dichloroethane, dioxane, tetrahydrofuran, diethyl ether or acetonitrile. 30 The processes (b) and (c) described above for preparing the compounds of the formula (I) are carried out in the presence of a base.

-31 Suitable bases are all customary proton acceptors. Preference is given to using alkali metal or alkaline earth metal hydroxides, alkali metal or alkaline earth metal carbonates or bicarbonates or nitrogen bases. Examples which may be mentioned are sodium hydroxide, calcium hydroxide, potassium carbonate, sodium bicarbonate, tri 5 ethylamine, dibenzylamine, diisopropylamine, pyridine, quinoline, diazabicyclo octane (DABCO), diazabicyclononene (DBN) and diazabicycloundecene (DBU). In the processes (a) and (b) described above, the reaction temperatures can be varied within a relatively wide range. In general, the processes are carried out at 10 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 preparing the compounds of the formula (1), generally 1 to 2 mol, preferably 1 to 1.5 mol, of the compound of the formula (III) and 1 to 2 mol, preferably 1 to 1.5 mol of the 15 compound of the formula (V) are employed per mole of amino derivative of the formula (Ia) and per mole of 5-aminoisothiazole of the formula (IV), respectively. In some cases, it is advantageous to employ the 5-aminoisothiazoles of the formula (IV) in the form of their hydrohalides, such as, in particular, as hydrochlorides. 20 Work-up and isolation of the end products is carried out in a generally known manner. The active compounds, having good crop tolerance and homeotherm safety, are suitable for controlling animal pests, in particular insects, arachnids and nematodes, 25 which are encountered in agriculture, in forestry, in the protection of stored products and of materials, and in the hygiene sector. They are preferably used as crop protection agents. They are active against normally sensitive and resistant species and against all or some stages of development. The abovementioned pests include: 30 From the order of Isopoda, for example, Oniscus asellus, Armadillidium vulgare and Porcellio scaber. From the order of the Diplopoda, for example, Blaniulus guttulatus.

-32 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. 5 From the order of the Collembola, for example, Onychiurus armatus. From the order of the Orthoptera, for example, Blatta orientalis, Periplaneta americana, Leucophaea maderae, Blatella germanica, Acheta domesticus, Gryllotalpa spp., Locusta migratoria migratorioides, Melanoplus differentialis and Schistocerca gregaria. 10 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, for example, Pediculus humanus corporis, Haematopinus spp. and Linognathus spp. From the order of the Mallophaga, for example, Trichodectes spp. and Damalinea 15 spp. From the order of the Thysanoptera, for example, Hercinothrips femoralis and Thrips tabaci. From the order of the Heteroptera, for example, Eurygaster spp., Dysdercus intermedius, Piesma quadrata, Cimex lectularius, Rhodnius prolixus and Triatoma 20 spp. From the order of the Homoptera, for example, 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 25 humuli, Rhopalosiphum padi, Empoasca spp., Euscelis bilobatus, Nephotettix cincticeps, Lecanium corni, Saissetia oleae, Laodelphax striatellus, Nilaparvata lugens, Aonidiella aurantii, Aspidiotus hederae, Pseudococcus spp. and Psylla spp. From the order of the Lepidoptera, for example, Pectinophora gossypiella, Bupalus piniarius, Cheimatobia brumata, Lithocolletis blancardella, Hyponomeuta padella, 30 Plutella maculipennis, Malacosoma neustria, Euproctis chrysorrhoea, Lymantria spp., Bucculatrix thurberiella, Phyllocnistis citrella, Agrotis spp., Euxoa spp., Feltia spp., Earias insulana, Heliothis spp., Spodoptera exigua, Mamestra brassicae, Panolis -33 flammea, Spodoptera litura, Spodoptera spp., Trichoplusia ni, Carpocapsa pomonella, Pieris spp., Chilo spp., Pyrausta nubilalis, Ephestia kuehniella, Galleria mellonella, Tineola bisselliella, Tinea pellionella, Hofnannophila pseudospretella, Cacoecia podana, Capua reticulana, Choristoneura fumiferana, Clysia ambiguella, 5 Homona magnanima and Tortrix viridana. From the order of the Coleoptera, for example, Anobium punctatum, Rhizopertha dominica, Bruchidius obtectus, Acanthoscelides obtectus, Hylotrupes bajulus, Agelastica alni, Leptinotarsa decemlineata, Phaedon cochleariae, Diabrotica spp., Psylliodes chrysocephala, Epilachna varivestis, Atomaria spp., Oryzaephilus 10 surinamensis, Anthonomus spp., Sitophilus spp., Otiorrhynchus sulcatus, Cosmopolites sordidus, Ceuthorrhynchus assimilis, Hypera postica, Dermestes spp., Trogoderma spp., Anthrenus spp., Attagenus spp., Lyctus spp., Meligethes aeneus, Ptinus spp., Niptus hololeucus, Gibbium psylloides, Tribolium spp., Tenebrio molitor, Agriotes spp., Conoderus spp., Melolontha melolontha, Amphimallon 15 solstitialis and Costelytra zealandica. From the order of the Hymenoptera, for example, Diprion spp., Hoplocampa spp., Lasius spp., Monomorium pharaonis and Vespa spp. From the order of the Diptera, for example, Aedes spp., Anopheles spp., Culex spp., Drosophila melanogaster, Musca spp., Fannia spp., Calliphora erythrocephala, 20 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 and Tipula paludosa. From the order of the Siphonaptera, for example, Xenopsylla cheopis and 25 Ceratophyllus spp. From the order of the Arachnida, for example, Scorpio maurus and Latrodectus mactans. From the order of the Acarina, for example, Acarus siro, Argas spp., Ornithodoros spp., Dermanyssus gallinae, Eriophyes ribis, Phyllocoptruta oleivora, Boophilus spp., 30 Rhipicephalus spp., Amblyomma spp., Hyalomma spp., Ixodes spp., Psoroptes spp., Chorioptes spp., Sarcoptes spp., Tarsonemus spp., Bryobia praetiosa, Panonychus spp. and Tetranychus spp.

- 34 The phytoparasitic nematodes include, for example, Pratylenchus spp., Radopholus similis, Ditylenchus dipsaci, Tylenchulus semipenetrans, Heterodera spp., Globodera spp., Meloidogyne spp., Aphelenchoides spp., Longidorus spp., Xiphinema spp., Trichodorus spp.. 5 The compounds of the formula (I) according to the invention are notable in particular for a good insecticidal and acaricidal action. They can be employed particularly successfully for controlling phytopathogenic 10 insects, such as, for example, against the mustard beetle larvae (Phaedon cochleariae), the green rice leaf hopper (Nephotettix cincticeps) and the caterpillars of the owlet moth (Spodoptera frugiperda) or for controlling phytopathogenic mites, such as, for example, against the common spider mite (Tetranychus urticae). 15 The active compounds can be converted into the customary formulations, such as solutions, emulsions, wettable powders, suspensions, powders, dusting agents, pastes, soluble powders, granules, suspension-emulsion concentrates, natural and synthetic materials impregnated with active compound, and very fine capsules in polymeric substances. 20 These formulations are produced in a known manner, for example by mixing the active compounds with extenders, that is liquid solvents and/or solid carriers, optionally with the use of surface-active agents, that is emulsifying agents and/or dispersing agents and/or foam-forming agents. 25 In the case of the use of water as an extender, organic solvents can, for example, also be used as auxiliary solvents. As liquid solvents, there are suitable in the main: aromatics, such as xylene, toluene or alkylnaphthalenes, chlorinated aromatics and chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chloroethylenes of 30 methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, for example 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 -35 ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents, such as dimethylformamide and dimethyl sulphoxide, as well as water. Suitable solid carriers are: for example ammonium salts and ground natural minerals, 5 such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, and ground synthetic minerals, such as highly disperse silica, alumina and silicates, as solid carriers for granules there are suitable: for example crushed and fractionated natural rocks such as calcite, marble, pumice, sepiolite and dolomite as well as synthetic granules of inorganic and organic meals, and granules 10 of organic material such as sawdust, coconut shells, maize cobs and tobacco stalks; as emulsifying and/or foam-forming agents there are suitable: for example non-ionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example alkylaryl polyglycol ethers, alkylsulphonates, alkylsulphates, arylsulphonates as well as albumen hydrolysis products; as dispersing 15 agents there are suitable: for example lignin-sulphite waste liquors and methylcellulose. Tackifiers such as carboxymethylcellulose and natural and synthetic polymers in the form of powders, granules or latices, such as gum arabic, polyvinyl alcohol and 20 polyvinyl acetate, as well as natural phospholipids, such as cephalins and lecithins, and synthetic phospholipids, can be used in the formulations. Further additives can be mineral and vegetable oils. It is possible to use colorants such as inorganic pigments, for example iron oxide, 25 titanium oxide and Prussian Blue, and organic dyestuffs, such as alizarin dyestuffs, azo dyestuffs and metal phthalocyanine dyestuffs, and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc. The formulations in general contain between 0.1 and 95 per cent by weight of active 30 compound, preferably between 0.5 and 90%.

- 36 The active compound of the invention can be present in its commercially customary formulations and in the use forms prepared from these formulations, in a mixture with other active compounds, such as insecticides, attractants, sterilants, bacteriocides, acaricides, nematicides, fungicides, growth regulators or herbicides. 5 The insecticides include, for example, phosphates, carbamates, carboxylates, chlorinated hydrocarbons, phenylureas, substances produced by microorganisms, etc. Particularly favourable co-components are, for example, those listed below: 10 Fungicides: 2-aminobutane; 2 -anilino- 4 -methyl-6-cyclopropyl-pyrimidine; 2',6'-dibromo-2 methyl-4'-trifluoromethoxy-4'-trifluoro-methyl-1,3-thiazole-5-carboxanilide; 2,6 dichloro-N-(4-trifluoromethylbenzyl)-benzamide; (E)-2-methoxyimino-N-methyl-2 (2-phenoxyphenyl)-acetamide; 8-hydroxyquinoline sulphate; methyl (E)-2-{2-[6-(2 15 cyanophenoxy)-pyrimidin-4-yloxy]-phenyl}-3-methoxyacrylate; methyl (E)-methox imino-[alpha-(o-tolyloxy)-o-tolyl]-acetate; 2-phenylphenol (OPP), aldimorph, ampropylfos, anilazine, azaconazole, benalaxyl, benodanil, benomyl, binapacryl, biphenyl, bitertanol, blasticidin-S, bromuconazole, bupirimate, buthiobate, 20 calcium polysulphide, captafol, captan, carbendazim, carboxin, quinomethionate, chloroneb, chloropicrin, chlorothalonil, chlozolinate, cufraneb, cymoxanil, cyproconazole, cyprofuram, dichlorophen, diclobutrazol, diclofluanid, diclomezin, dicloran, diethofencarb, difenoconazole, dimethirimol, dimethomorph, diniconazole, dinocap, diphenylamine, 25 dipyrithion, ditalimfos, dithianon, dodine, drazoxolon, edifenphos, epoxyconazole, ethirimol, etridiazole, fenarimol, fenbuconazole, fenfuram, fenitropan, fenpiclonil, fenpropidin, fenpropimorph, fentin acetate, fentin hydroxide, ferbam, ferimzone, fluazinam, fludioxonil, fluoromide, fluquinconazole, flusilazole, flusulphamide, flutolanil, 30 flutriafol, folpet, fosetyl-aluminium, fthalide, fuberidazole, furalaxyl, flrmecyclox, guazatine, hexachlorobenzene, hexaconazole, hymexazol, -37 imazalil, imibenconazole, iminoctadine, iprobenfos (IBP), iprodione, isoprothiolane, kasugamycin, copper preparations such as: copper hydroxide, copper naphthenate, copper oxychloride, copper sulphate, copper oxide, oxine-copper and Bordeaux mixture, 5 mancopper, mancozeb, maneb, mepanipyrim, mepronil, metalaxyl, metconazole, methasulphocarb, methfuroxam, metiram, metsulphovax, myclobutanil, nickel dimethyldithiocarbamate, nitrothal-isopropyl, nuarimol, ofurace, oxadixyl, oxamocarb, oxycarboxin, pefurazoate, penconazole, pencycuron, phosdiphen, phthalide, pimaricin, piperalin, 10 polycarbamate, polyoxin, probenazole, prochloraz, procymidone, propamocarb, propiconazole, propineb, pyrazophos, pyrifenox, pyrimethanil, pyroquilon, quintozene (PCNB), sulphur and sulphur preparations, tebucanozole, tecloftalam, tecnazene, tetraconazole, thiabendazole, thicyofen, 15 thiophanate-methyl, thiram, tolclophos-methyl, tolylfluanid, triadimefon, triadimenol, triazoxide, trichlamide, tricyclazole, tridemorph, triflumizole, triforine, triticonazole, validamycin A, vinclozolin, zineb, ziram. 20 Bactericides: bronopol, dichlorophen, nitrapyrin, nickel dimethyldithiocarbamate, kasugamycin, octhilinone, furancarboxylic acid, oxytetracycline, probenazole, streptomycin, tecloftalam, copper sulphate and other copper preparations. 25 Insecticides/Acaricides/Nematicides: abamectin, AC 303 630, acephate, acrinathrin, alanycarb, aldicarb, alphamethrin, amitraz, avermectin, AZ 60541, azadirachtin, azinphos A, azinphos M, azocyclotin. Bacillus thuringiensis, bendiocarb, benfuracarb, bensultap, beta-cyfluthrin, 30 bifenthrin, BPMC, brofenprox, bromophos A, bufencarb, buprofezin, butocarboxin, butylpyridaben, -38 cadusafos, carbaryl, carbofuran, carbophenothion, carbosulphan, cartap, CGA 157 419, CGA 184699, chloethocarb, chlorethoxyfos, chlorfenvinphos, chlorfluazuron, chlormephos, chlorpyrifos, chlorpyrifos M, cis-resmethrin, clocythrin, clofentezine, cyanophos, cycloprothrin, cyfluthrin, cyhalothrin, cyhexatin, 5 cypermethrin, cyromazine, deltamethrin, demeton-M, demeton-S, demeton-S-methyl, diafenthiuron, diazinon, dichlofenthion, dichlorvos, dicliphos, dicrotophos, diethion, diflubenzuron, dimethoate, dimethylvinphos, dioxathion, disulphoton, edifenphos, emamectin, esfenvalerate, ethiofencarb, ethion, ethofenprox, 10 ethoprophos, etrimphos, fenamiphos, fenazaquin, fenbutatin oxide, fenitrothion, fenobucarb, fenothiocarb, fenoxycarb, fenpropathrin, fenpyrad, fenpyroximate, fenthion, fenvalerate, fipronil, fluazinam, flucycloxuron, flucythrinate, flufenoxuron, flufenprox, fluvalinate, fonophos, formothion, fosthiazate, fubfenprox, furathiocarb, 15 HCH, heptenophos, hexaflumuron, hexythiazox, imidacloprid, iprobenfos, isazophos, isofenphos, isoprocarb, isoxathion, ivermectin, lambda-cyhalothrin, lufenuron, malathion, mecarbam, mevinphos, mesulfenphos, metaldehyde, methacrifos, methamidophos, methidathion, methiocarb, methomyl, metolcarb, milbemectin, 20 monocrotophos, moxidectin, naled, NC 184, NI 25, nitenpyram, omethoate, oxamyl, oxydemethon M, oxydeprofos, parathion A, parathion M, permethrin, phenthoate, phorate, phosalone, phosmet, phosphamidon, phoxim, pirimicarb, pirimiphos M, pirimiphos A, profenofos, 25 promecarb, propaphos, propoxur, prothiofos, prothoate, pymetrozin, pyrachlophos, pyradaphenthion, pyresmethrin, pyrethrum, pyridaben, pyrimidifen, pyriproxifen, quinalphos, RH 5992, salithion, sebufos, silafluofen, sulphotep, sulprofos, 30 tebufenozid, tebufenpyrad, tebupirimiphos, teflubenzuron, tefluthrin, temephos, terbam, terbufos, tetrachlorvinphos, thiafenox, thiodicarb, thiofanox, thiomethon, -39 thionazin, thuringiensin, tralomethrin, triarathen, triazophos, triazuron, trichlorfon, triflumuron, trimethacarb, vamidothion, XMC, xylylcarb, YI 5301/5302, zetamethrin. 5 A mixture with other known active compounds, 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 10 formulations, as a mixture with synergists. Synergists are compounds which increase the action of the active compounds without it being necessary for the synergist added to be active itself The active compound content of the use forms prepared from the commercially 15 available formulations can vary within wide limits. The active compound concentration of the use forms can be from 0.0000001 to 95% by weight of active compound, preferably between 0.0001 and 1% by weight. The compounds are employed in a customary manner appropriate for the use forms. 20 When used against hygiene pests and pests of stored products, the active compounds are distinguished by an excellent residual action on wood and clay as well as a good stability to alkali on limed substrates. 25 The active compounds according to the invention are not only active against plant, hygiene and stored-product pests, but also, in the veterinary medicine sector, against animal parasites (ectoparasites), such as ixodid ticks, argasid ticks, scab mites, trombiculid mites, flies (stinging and sucking), parasitic fly larvae, lice, hair lice, bird lice and fleas. These parasites include: 30 From the order of the Anoplurida, for example, Haematopinus spp., Linognathus spp., Pediculus spp., Phtirus spp., Solenopotes spp.

-40 From the order of the Mallophagida and the sub-orders Amblycerina and Ischnocerina, for example, Trimenopon spp., Menopon spp., Trinoton spp., Bovicola spp., Werneckiella spp., Lepikentron spp., Damalina spp., Trichodectes spp., Felicola 5 spp. From the order of the Diptera and the sub-orders of the Nematocerina and Brachycerina, for example, Aedes spp., Anopheles spp., Culex spp., Simulium spp., Eusimulium spp., Phlebotomus spp., Lutzomyia spp., Culicoides spp., Chrysops spp., 10 Hybomitra spp., Atylotus spp., Tabanus spp., Haematopota spp., Philipomyia spp., Braula spp., Musca spp., Hydrotaea spp., Stomoxys spp., Haematobia spp., Morellia spp., Fannia spp., Glossina spp., Calliphora spp., Lucilia spp., Chrysomyia spp., Wohlfahrtia spp., Sarcophaga spp., Oestrus spp., Hypoderma spp., Gasterophilus spp., Hippobosca spp., Lipoptena spp. and Melophagus spp. 15 From the order of the Siphonapterida, for example, Pulex spp., Ctenocephalides spp., Xenopsylla spp. and Ceratophyllus spp. From the order of the Heteropterida, for example, Cimex spp., Triatoma spp., 20 Rhodnius spp. and Panstrongylus spp. From the order of the Blattarida, for example, Blatta orientalis, Periplaneta americana, Blattela germanica and Supella spp. 25 From the sub-class of the Acaria (Acarida) and the orders of the Meta- and Mesostigmata, for example Argas spp., Ornithodorus spp., Otobius spp., Ixodes spp., Amblyomma spp., Boophilus spp., Dermacentor spp., Haemaphysalis spp., Hyalomma spp., Rhipicephalus spp., Dermanyssus spp., Raillietia spp., Pneumonyssus spp., Sternostoma spp. and Varroa spp. 30 From the order of the Actinedida (Prostigmata) and Acaridida (Astigmata), for example Acarapis spp., Cheyletiella spp., Ornithocheyletia spp., Myobia spp., -41 Psorergates spp., Demodex spp., Trombicula spp., Listrophorus spp., Acarus spp., Tyrophagus spp., Caloglyphus spp., Hypodectes spp., Pterolichus spp., Psoroptes spp., Chorioptes spp., Octodectes spp., Sarcoptes spp., Notoedres spp., Knemidocoptes spp., Cytodites spp. and Laminosioptes spp. 5 For example, they exhibit good development-inhibitory action against Lucilia cuprina fly larvae and also good inhibition of oviposition of Boophilus microplus. The active compounds of the formula (1) according to the invention are also suitable 10 for controlling arthropods which attack agricultural livestock, such as, for example, cattle, sheep, goats, horses, pigs, donkeys, camels, buffalo, rabbits, chickens, turkeys, ducks, geese, honey bees, other domestic animals, such as, for example, dogs, cats, cage birds, aquarium fish, and so-called experimental animals such as, for example, hamsters, guinea-pigs, rats and mice. By controlling these arthropods, it is intended 15 to reduce mortality and decreased performance (in meat, milk, wool, hides, eggs, honey and the like), so that more economical and simpler animal keeping is made possible by using the active compounds according to the invention. In the veterinary sector, the active compounds according to the invention are used in 20 a known manner by enteral administration, for example in the form of tablets, capsules, drinks, drenches, granules, pastes, boluscs, the feed-through method, suppositories, by parenteral administration, such as, for example, by means of injections (intramuscular, subcutaneous, intravenous, intraperitoneal and the like), implants, by nasal application, by dermal administration, for example in the form of 25 dipping or bathing, spraying, pouring-on and spotting-on, washing, dusting, and with the aid of shaped articles which comprise active compound, such as collars, ear tags, tail marks, limb bands, halters, marking devices and the like. When administered to livestock, poultry, domestic animals and the like, the active 30 compounds of the formula (I) can be used as formulations (for example powders, emulsions, flowables) which comprise the active compounds in an amount of 1 to -42 80% by weight, either directly or after dilution by a factor of 100 to 10,000, or they may be used in the form of a chemical bath. Furthermore, it has been found that the compounds of the formula (I) according to 5 the invention have a potent insecticidal action against insects which destroy industrial materials. The following insects may be mentioned by way of example and as being preferred, but without any limitation: 10 Beetles, such as Hylotrupes bajulus, Chlorophorus pilosis, Anobium punctatum, Xestobium rufovillosum, Ptilinus pecticomis, Dendrobium pertinex, Ernobius mollis, Priobium carpini, Lyctus brunneus, Lyctus africanus, Lyctus planicollis, Lyctus linearis, Lyctus 15 pubescens, Trogoxylon aequale, Minthes rugicollis, Xyleborus spec., Tryptodendron spec., Apate monachus, Bostrychus capucins, Heterobostrychus brunneus, Sinoxylon spec., Dinoderus minutus. Dermapterans, such as 20 Sirex juvencus, Urocerus gigas, Urocerus gigas taignus, Urocerus augur. Termites, such as Kalotermes flavicollis, Cryptotermes brevis, Heterotermes indicola, Reticulitermes flavipes, Reticulitermes santonensis, Reticulitermes lucifugus, Mastotermes 25 darwiniensis, Zootermopsis nevadensis, Coptotermes formosanus. Bristletails, such as Lepisma saccharina. 30 Industrial materials are to be understood as meaning, in the present context, non-live materials such as, preferably, synthetic materials, glues, sizes, paper and board, leather, wood and timber products, and paint.

-43 The materials to be very particularly protected against attack by insects are wood and timber products. 5 Wood and timber products which can be protected by the composition according to the invention or mixtures comprising such a composition are to be understood as meaning, for example, construction timber, wooden beams, railway sleepers, bridge components, jetties, wooden vehicles, boxes, pallets, containers, telephone poles, wood lagging, windows and doors made of wood, plywood, particle board, joiner's 10 articles, or wood products which, quite generally, are used in the construction of houses or in joinery. The active compounds can be used as such, in the form of concentrates or generally customary formulations, such as powders, granules, solutions, suspensions, 15 emulsions or pastes. The formulations mentioned can be prepared in a manner known per se, for example by mixing the active compounds with at least one solvent or diluent, emulsifier, dispersant and/or binder or fixative, water repellent, if appropriate desiccants and UV 20 stabilizers and, if appropriate, colorants and pigments and other processing auxiliaries. The insecticidal compositions or concentrates used for the protection of wood and wooden materials comprise the active compound according to the invention at a 25 concentration of 0.0001 to 95% by weight, in particular 0.001 to 60% by weight. The amount of the compositions or concentrates employed depends on the species and the occurrence of the insects and on the medium. The optimum rate of application can be determined upon use in each case by test series. However, in 30 general, it suffices to employ 0.0001 to 20% by weight, preferably 0.001 to 10% by weight, of the active compound, based on the material to be protected.

-44 The solvent and/or diluent used is an organochemical solvent or solvent mixture and/or an oily or oil-type organochemical solvent or solvent mixture of low volatility and/or a polar organochemical solvent or solvent mixture and/or water and, if appropriate, an emulsifier and/or wetting agent. 5 Organochemical solvents which are preferably employed are oily or oil-type solvents having an evaporation number of above 35 and a flashpoint of above 30'C, preferably above 45*C. Substances which are used as such oily and oil-type solvents which have low volatility and are insoluble in water are suitable mineral oils or their 10 aromatic fractions, or mineral-oil-containing solvent mixtures, preferably white spirit, petroleum and/or alkylbenzene. Substances which are advantageously used are mineral oils with a boiling range of 170 to 220 0 C, white spirit with a boiling range of 170 to 220 0 C, spindle oil with a 15 boiling range of 250 to 350*C, petroleum or aromatics of boiling range 160 to 280*C, essence of turpentine and the like. In a preferred embodiment, liquid aliphatic hydrocarbons with a boiling range of 180 to 210'C or high-boiling mixtures of aromatic and aliphatic hydrocarbons with a 20 boiling range of 180 to 220*C and/or spindle oil and/or monochloronaphthalene, preferably a-monochloronaphthalene, are used. The organic oily or oil-type solvents of low volatility having an evaporation number of above 35 and a flashpoint of above 30*C, preferably above 45'C, can be partially 25 replaced by organochemical solvents of high or medium volatility, with the proviso that the solvent mixture also has an evaporation number of above 35 and a flashpoint of above 30 0 C, preferably above 45*C, and that the insecticide/fungicide mixture is soluble or emulsifiable in this solvent mixture. 30 In a preferred embodiment, part of the organochemical solvent or solvent mixture is replaced by an aliphatic polar organochemical solvent or solvent mixture. Substances which are preferably used are aliphatic organochemical solvents having hydroxyl -45 and/or ester and/or ether groups, such as, for example, glycol ether, esters and the like. The organochemical binders used within the scope of the present invention are the 5 synthetic resins and/or binding drying oils which are known per se and can be diluted with water and/or are soluble or dispersible or emulsifiable in the organochemical solvents employed, in particular binders composed of, or comprising, an acrylate resin, a vinyl resin, for example polyvinyl acetate, polyester resin, polycondensation or polyaddition resin, polyurethane resin, alkyd resin or modified alkyd resin, phenol 10 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 the binder can be employed in the form of an emulsion, 15 dispersion or solution. Up to 10% by weight of bitumen or bituminous substances can also be used as binders. In addition, colorants, pigments, water repellents, odour masking substances and inhibitors or anticorrosives known per se and the like can also be employed. 20 The composition or the concentrate preferably comprises, in accordance with the invention, at least one alkyd resin or modified alkyd resin and/or a drying vegetable oil as the organochemical binder. Preferably used according to the invention are alkyd resins with an oil content of over 45% by weight, preferably 50 to 68% by weight. 25 All or some of the abovementioned binder can be replaced by a fixative (mixture) or a plasticizer (mixture). These additives are intended to prevent volatilization of the active compounds and crystallization or precipitation. They preferably replace 0.01 to 30% of the binder (based on 100% of binder employed). 30 The plasticizers are from the chemical classes of the phthalic esters, such as dibutyl phthalate, dioctyl phthalate or benzyl butyl phthalate, the phosphoric esters, such as -46 tributyl phosphate, the adipic esters, such as di-(2-ethylhexyl) adipate, the stearates, such as butyl stearate or amyl stearate, the oleates, such as butyl oleate, the glycerol ethers or relatively high-molecular-weight glycol ethers, glycerol esters and p toluene-suiphonic esters. 5 Fixatives are chemically based on polyvinyl alkyl ethers, such as, for example, polyvinyl methyl ether, or ketones, such as benzophenone or ethylene benzophenone. Particularly suitable as a solvent or diluent is also water, if appropriate as a mixture 10 with one or more of the abovementioned organochemical solvents or diluents, emulsifiers and dispersants. Particularly effective protection of wood is achieved by large-scale industrial impregnation processes, for example vacuum, double-vacuum or pressure processes. 15 If appropriate, the ready-to-use compositions can additionally comprise further insecticides and additionally one or more fungicides. Suitable additional components which may be admixed are, preferably, the 20 insecticides and fungicides mentioned in WO 94/29 268. The compounds mentioned in that document are expressly part of the present application. Very particularly preferred components which may be admixed are insecticides, such as chlorpyriphos, phoxim, silafluofin, alphamethrin, cyfluthrin, cypermethrin, 25 deltamethrin, permethrin, imidacloprid, NI-25, flufenoxuron, hexaflumuron and triflumuron, and fungicides, such as epoxyconazole, hexaconazole, azaconazole, propiconazole, tebuconazole, cyproconazole, metconazole, imazalil, dichlorofluanide, tolylfluanide, 3-iodo-2-propinylbutyl carbamate, N-octyl isothiazolin-3-one and 4 ,5-dichloro-N-octylisothiazolin-3-one. 30 The active compounds according to the invention also have potent microbicidal activity and can be employed practically for controlling undesirable microorganisms.

-47 The active compounds are suitable for use as crop protection agents, in particular as fungicides. Fungicides are employed in crop protection for controlling Plasmodiophoromycetes, Oomycetes, Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes and 5 Deuteromycetes. Bactericides are employed in crop protection for controlling Pseudomonadaceae, Rhizobiaceae, Enterobacteriaceae, Corynebacteriaceae and Streptomycetaceae. 10 Some pathogens causing fungal and bacterial diseases which come under the generic names listed above are 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; 15 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; 20 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 fuliginea; 25 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 (conidia form: Drechslera, syn: Helminthosporium); Cochliobolus species, such as, for example, Cochliobolus sativus 30 (conidia form: Drechslera, syn: Helminthosporium); Uromyces species, such as, for example, Uromyces appendiculatus; Puccinia species, such as, for example, Puccinia recondita; -48 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; 5 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; 10 Cercospora species, such as, for example, Cercospora canescens; Alternaria species, such as, for example, Alternaria brassicae; and Pseudocercosporella species, such as, for example, Pseudocercosporella herpotrichoides. 15 The fact that the active compounds are well tolerated by plants at the concentrations required for controlling plant diseases permits the treatment of aerial parts of plants, of propagation stock and seeds, and of the soil. They can be employed particularly successfully against the causative organism of 20 downy mildew of grapes (Plasmopara viticola), and also against rice blast (Pyricularia oryzae). In addition, they have broad in vitro activity against phytopathogenic fungi. 25 When used as fungicides, the active compounds according to the invention can be employed as such, in the form of their commercial formulations or as the use forms prepared therefrom, such as ready-to-use solutions, suspensions, wettable powders, pastes, soluble powders, dusts and granules. They are applied in the customary manner, for example by watering, spraying, atomizing, scattering, foaming, brushing 30 on and the like. It is further possible to apply the active compounds by the ultra-low volume method or to inject the active compound formulation, or the active compound itself, into the soil. The seed of the plants can also be treated.

- 49 In the treatment of parts of plants, the active compound concentrations in the use forms can be varied within a substantial range: in general, they are between 1 and 0.0001% by weight, preferably between 0.5 and 0.001% by weight. 5 In the treatment of seed, amounts of active compound of from 0.001 to 50 g, preferably 0.01 to 10 g, are generally required per kilogram of seed. In the treatment of the soil, active compound concentrations of from 0.00001 to 0.1% 10 by weight, preferably from 0.0001 to 0.02% by weight, are required at the treatment site. The preparation and the use of the active compounds according to the invention is illustrated by the following examples.

- 50 Preparation Examples Example A-1

H

3 C 7 CI 5 CO CH - H S N '- C H 0-I "NH 5H 2GjC2 (Process a) 2.5 g (5.9 mmol) of 4 -chloro-3-methyl-5-[4-(4-nitrophenoxy)]phenylacetylamino isothiazole and 2.0 g (35.4 mmol) of iron powder in 50 ml of 50% strength ethanol are heated to reflux temperature and admixed dropwise with 0.16 ml of 98% strength 10 sulphuric acid in 5 ml of 50% strength ethanol. The reaction mixture is heated under reflux for 3 hours and then filtered while still hot. The filtrate is concentrated under reduced pressure. This gives 1.2 g (55% of theory) of 5-[ 4

-(

4 -aminophenoxy)]phenylacetylamino-4 chloro-3-methyl-isothiazole of melting point 226*C. 15 Example A-2

H

3 C CI S N CH2 2 O a NH-CO-C(CH 3

)

3 H (Process b) 20 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 admixed with 0.3 g (3.8 mmol) of pyridine. 0.25 g (2.1 mmol) of pivaloyl chloride in 2 ml of dichloromethane are subsequently added dropwise with stirring, and the reaction mixture is stirred at 25"C for 18 hours. The reaction solution is then washed 25 successively with water and 10% strength hydrochloric acid, dried and concentrated. This gives 0.8 g (80% of theory) of 5-[4-(4-t-butyl-carbonylaminophenoxy)]phenyl acetylamino-4-chloro-3-methyl-isothiazole having a logP (pH 4.5) = 3.29.

-51 Example A-3

H

3 C CI I j CO S N CH2 ,)O-C [ NH-COOC 3

H

7 -i H 5 (Process b) 0.32 g (3.8 mmol) of sodium bicarbonate is initially added to 0.78 g (1.9 mmol) of 5-[ 4

-(

4 -aminophenoxy)]phenylacetylamino-4-chloro-3-methylisothiazole (Example 1) in 10 ml of acetone, and 2.1 ml (2.1 mmol) of a 1 molar solution of isopropyl chloroformate in toluene are subsequently added dropwise. The mixture is allowed to 10 stir at 25"C for 18 hours and concentrated, and the residue is taken up in water, filtered off and dried. This gives 0.6 g (69% of theory) of 5-[ 4

-(

4 -isopropyloxycarbonylaminophen oxy)]phenylacetylamino-4-chloro-3-methyl-isothiazole having a logP (pH 4.5) = 3.43.

- 52 Similarly to the Preparation Examples A-i to A-3, and/or in accordance with the general preparation procedures, the following compounds according to the invention are obtained: 5 Table A Ri R 2 CO

NR

4 R ( IA-0)

R

3 Ex. R 1

R

2

R

3 Y R4

R

5 logP value No. (pH2) *) or m.p. A-4 C 2

H

5 CN H CH 2

-SO

2

CH

3 H 2.75 A-5 CH 3 Cl H CH 2

-SO

2

CH

3 H 2.55 A-6 CH 3 Cl H CH 2

-COCH

3 H 2.39 A-7 CH 3 Cl H CH 2

-CO-CH=CH-CH

3 H 2.85 A-8 CH 3 Cl H CH 2

-COCH

2 Cl H 2.77 A-9 CH 3 CI H CH 2 -coo_ H 3.60 A-10 CH 3 Cl H CH2 -CO H 3.22 A-11 CH 3 Cl H CH 2

-COO-CH

2

-CH=CH

2 H 3.31 A-12 CH 3 Cl H CH2 -COO-C 2

H

5 H 3.14 A-13 CH 3 Cl H CH 2 -802 H 3.20 A-14 CH 3 Cl H CH2 0 H 3.28 CT F 3 174 0 C *) logP = Logarithm to base ten of the n-octanol/water partition coefficient, 10 determined by reversed phase HPLC analysis using H 2 0/CH 3

CN

- 53 Table B N 1 3 N COYO

NR

4

R

5 (18-0) Ex. R 1

R

2

R

3 Y R4

R

5 logP value No. (pH2) *) or m.p. B-1 C 2

H

5 C1 H CH 2

-SO

2

CH

3 H 1.81 B-2 C 2

H

5 Cl H CH 2

-COO-CH

2

-CH=CH

2 H 2.45 B-3 C 2

H

5 Cl H CH 2 H H 1.01 B-4 C 2

H

5 Cl H CH 2 0 H 2.42 tBu 120 0 C B-5 C 2

H

5 Cl H CH 2 0 H 1.68 kCH 154 0 C B-6 C 2 HS Cl H CH 2 0 H 2.3 0 CH 3 133 0 C B-7 C 2

H

5 Cl H CH 2 O CH3 H 2.59 O CH 3 142 0 C B-8 C 2

H

5 Cl H CH 2 0 H 2.36 A CF 170 0 C B-9 C 2

H

5 CI H CH2 0 H 2.64 AO) B-10 C 2

H

5 Cl H CH 2 0 H 2.01

SCH

3 1680C - 54 Table B (continued) Ex. R 1

R

2

R

3 Y R4 R 5 logP value No. (pH2) *) or m.p. B-1I C 2

H

5 Cl H CH 2 0HC CH H 3.48 C1C CI B-12 C2H 5 Cl H CH 2 0 H 2.83 I 115*C 5 *) logP = Logarithm to base ten of the n-octanol/water partition coefficient, determined by reversed phase HPLC analysis using H 2 0/CH 3

CN

- 55 Use Examples Example A 5 Nephotettix test Solvent: 7 parts by weight of dimethylformamide Emulsifier: 1 part by weight of alkylaryl polyglycol ether 10 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 being dipped into the preparation of 15 active compound of the desired concentration and are populated with the green rice leaf hoppers (Nephotettix cincticeps) while the seedlings are still moist. After the desired period of time, the kill in % is determined. 100% means that all leaf hoppers have been killed; 0% means that none of the leaf hoppers have been killed. 20 In this test, for example, the compounds of Preparation Examples A-1, A-2, A-4, A-5, A-6, A-9 and A-Il effect, at an exemplary active compound concentration of 0.1%, in each case a kill of 100% after 6 days.

-56 Example B Phaedon larvae test 5 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 10 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 are populated with mustard beetle larvae (Phaedon cochleariae) while the leaves are still moist. 15 After the desired period of time, the kill in % is determined. 100% means that all beetle larvae have been killed; 0% means that none of the beetle larvae have been killed. 20 In this test, for example, the compounds of Preparation Examples A-1, A-2, A-4, A-5, A-6, A-7, A-8, A-9, A-10 and A- 11 effect, at an exemplary active compound concentration of 0.1%, in each case a kill of 100% after 7 days.

- 57 Example C Spodoptera frugiperda test 5 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 10 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 are populated with caterpillars of the owlet moth (Spodoptera frugiperda) while the leaves are still moist. 15 After the desired period of time, the kill in % is determined. 100% means that all caterpillars been killed; 0% means that none of the caterpillars have been killed. In this test, for example, the compounds of Preparation Examples A-1, A-2, A-4, 20 A-5, A-6, A-7, A-8, A-9, A-10 and A-II effect, at an exemplary active compound concentration of 0.1%, in each case a kill of 100% after 7 days.

- 58 Example D Tetranychus test (OP-resistant/dip treatment) 5 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 10 emulsifier, and the concentrate is diluted with emulsifier-containing water to the desired concentrations. Bean plants (Phaseolus vulgaris) which are heavily infested by all stages of the common spider mite (Tetranychus urticae) are dipped into a preparation of active 15 compound of the desired concentration. After the desired period of time, the effect in % is determined. 100% means that all spider mites have been killed; 0% means that none of the spider mites have been killed. 20 In this test, for example, at an exemplary active compound concentration of 0.01%, the compound of Preparation Example A- 10 effects a kill of 95% and the compound of Preparation Example A-11 a kill of 100%, in each case after 7 days.

- 59 Example E Plasmopara test (grapevine) / protective 5 Solvent: 47 parts by weight of acetone Emulsifier: 3 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 amounts of solvent and emulsifier, and the 10 concentrated is diluted with water to the desired concentration. To test for protective activity, young plants are sprayed with the preparation of active compound at the stated application rate. After the spray coating has dried on, the plants are inoculated with an aqueous spore suspension of Plasmopara viticola and 15 then remain in an incubation cabin at approximately 20*C and 100% relative atmospheric humidity for 1 day. The plants are subsequently placed in a greenhouse at approxiamtely 21*C and approximately 90% relative atmospheric humidity for 5 days. The plants are then moistened and placed in an incubation cabin for 1 day. 20 Evaluation is carried out 6 days after the inoculation. 0% means an efficacy which corresponds to that of the control, whereas an efficacy of 100% means that no infection is observed. In this test, for example, at an exemplary application rate of 100 g/ha, the compound 25 of Preparation Example A-6 exhibits an efficacy of 94% and the compound of Preparation Example A- 10 an efficacy of 99%.

- 60 Example F Pyricularia test (rice) / protective 5 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 10 with water and the stated amount of emulsifier to the desired concentration. To test for protective activity, young rice plants are sprayed with the preparation of active compound at the stated application rate. After the spray coating has dried on, the plants are inoculated with an aqueous spore suspension of Pyricularia oryzae. The 15 plants are subsequently 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, whereas an efficacy of 100% means that no 20 infection is observed. In this test, for example, at an exemplary application rate of 750 g/ha, the compounds of Preparation Examples A-7, A-8 and A- 10 exhibit an efficacy of in each case 90% and the compounds of Preparation Examples A-9 and A-l1 an efficacy of in each 25 case 100%.

- 61 Example G Blowfly larvae test/development-inhibitory action 5 Test animals: Lucilia cuprina larvae Solvent: Dimethyl sulphoxide 20 mg of active compound are dissolved in 1 ml of dimethyl sulphoxide, more dilute concentrations are prepared by dilution with distilled water. 10 About 20 Lucilia cuprina larvae are introduced into a test tube which contains about 1 cm 3 of horsemeat and 0.5 ml of the preparation of active compound to be tested. After 24 hours and 48 hours, the effectiveness of the preparation of active compound is determined. The test tubes are transferred into beakers whose bottom 15 is covered with sand. After a further 2 days, the test tubes are removed and the pupae are counted. The effect of the preparation of active compound is assessed by the number of flies which have hatched after 1.5 times the development period of an untreated control. 20 100% means that no flies have hatched; 0% means that all flies have hatched normally. In this test, for example, the compounds of Preparation Examples A-9 and A- 10 exhibit, at an exemplary active compound concentration of 100 jig, in each case 25 an effect of 100%.

- 62 Example H Test with Boophilus microplus resistant/SP-resistant Parkhurst strain 5 Test animals: Adult females which have sucked themselves full Solvent: Dimethyl sulphoxide 20 mg of active compound are dissolved in 1 ml of dimethyl sulphoxide, more dilute concentrations are prepared by dilution with the same solvent. 10 The test is carried out in 5 replications. I pl of the solutions is injected into the abdomen and the animals are transferred to dishes and kept in a climatized room. The effect is determined by inhibition of oviposition. 100% means that no tick has laid any eggs. 15 In this test, for example, the compounds of Preparation Examples A-9 and A-10 exhibit, at an exemplary active compound concentration of 20 pg, in each case an effect of 100%.

Claims (11)

1. Compounds of the formula (I) NR 4 R 5 Het NCO 5 R 3 X in which Het represents one of the heterocycles 1 R, or N .. > where RI represents alkyl, halogenoalkyl, alkoxyalkyl, alkylthioalkyl, alkoxy, alkylthio or optionally substituted cycloalkyl, R 2 represents hydrogen, halogen, cyano, nitro, thiocyanato, 15 alkoxycarbonyl, alkenyloxycarbonyl, alkylthio, halogeno alkylthio, alkylsulphinyl, halogenoalkylsulphinyl, alkyl sulphonyl, halogenoalkylsulphonyl or thiocarbamoyl or R 1 and R 2 together with the carbon atoms to which they are 20 attached represent an optionally substituted saturated or unsaturated 5- or 6-membered carbocyclic ring, R 3 represents hydrogen, alkyl, halogenoalkyl, alkoxyalkyl, alkylcarbonyl, alkoxycarbonyl, alkenyloxycarbonyl, alkylsulphonyl, in each case 25 optionally substituted arylcarbonyl, aryloxycarbonyl, arylsulphonyl or arylalkyl or optionally substituted cycloalkyl, - 64 R 4 and R 5 independently of one another each represent hydrogen or represent the radicals -COR 6 , -COOR 7 and -S0 2 R 8 where 5 R 6 , R 7 and R 8 independently of one another each represent alkyl, halogenoalkyl, alkoxyalkyl, alkylthioalkyl, alkylcarbonyl oxyalkyl, alkoxycarbonylalkyl; alkenyl, halogenoalkenyl; alkinyl, halogenoalkinyl; in each case optionally substituted cycloalkyl, cycloalkylalkyl, cycloalkoxyalkyl or cycloalkyl 10 thioalkyl; in each case optionally substituted aryl, arylalkyl, aryloxyalkyl or arylthioalkyl or represent an optionally substituted heterocycle, XI and X 2 independently of one another each represent halogen, nitro, cyano, 15 alcyl, alkoxy or halogenoalkyl, m and n independently of one another each represent 0, 1, 2 or 3 and Y represents in each case optionally substituted alkylene, alkenylene or 20 alkenylenoxy.

2. Compounds of the formula (I) according to Claim I in which Het represents the heterocycles 25 i R 2 R 2 R~ N S N R N R o r R w h e r e RI represents CI-C 4 -alkyl, CI-C 4 -halogenoalkyl having 1 to 5 identical or different halogen atoms, such as fluorine, chlorine -65 and bromine atoms, CI-C 4 -alkoxy-CI-C 4 -alkyl, CI-C 4 alkylthio-C-C 4 -alkyl, CI-C 4 -alkoxy, C 1 -C 4 -alkylthio or represents C

3 -C 6 -cycloacyl which is optionally mono- to trisubstituted by identical or different substituents from the 5 group consisting of C -C 4 -alkyl and halogen, R 2 represents hydrogen, halogen, cyano, nitro, thiocyanato, CI-C 4 alkoxy-carbonyl, C 2 -C 4 -alkenyloxy-carbonyl, C 1 -C 4 -alkylthio, CI-C 4 -halogenoalkylthio having 1 to 5 identical or different 10 halogen atoms, such as fluorine or chlorine atoms, CI-C 4 alkylsulphinyl, C 1 -C 4 -halogenoalcylsulphinyl having I to 5 identical or different halogen atoms, such as fluorine or chlorine atoms, C 1 -C 4 -alkylsulphonyl, CI-C 4 -halogenoalkyl sulphonyl having 1 to 5 identical or different halogen atoms, 15 such as fluorine or chlorime atoms, or represents thiocarbamoyl; or RI and R 2 together with the carbon atoms to which they are attached represent a carbocyclic 5- or 6-membered ring which is 20 optionally mono- to trisubstituted by identical or different substituents, suitable substituents being halogen, CI-C 4 -alkyl, C 1 -C 4 -halogenoalkyl, CI-C 4 -alkoxy, C 1 -C 4 -halogenoalkoxy, nitro and cyano, 25 R 3 represents hydrogen, CI-C 4 -alkyl, CI-C 4 -halogenoalkyl having 1 to 5 identical or different halogen atoms, such as fluorine or chlorine atoms, CI-C 4 -alkoxy-CI-C 4 -alkyl, C 1 -C 4 -alkyl-carbonyl, C 1 -C 4 alkoxy-carbonyl, C 2 -C 4 -alkenyloxy-carbonyl, CI-C 4 -alkylsulphonyl, represents phenylcarbonyl, phenyloxycarbonyl, phenylsulphonyl or 30 benzyl, each of which is optionally mono- to trisubstituted in the phenyl ring by identical or different substituents, suitable substituents being in each case halogen, nitro, cyano, CI-C 4 -alkyl, CI-C 2 - - 66 halogenoalkyl having 1 to 5 identical or different halogen atoms, such as fluorine or chlorine atoms, CI-C 4 -alkoxy, C 1 -C 4 -alkylthio, C 1 -C 2 halogenoalkoxy having 1 to 5 identical or different halogen atoms, such as fluorine or chorine atoms, or C 1 -C 2 -halogenoalkylthio having 5 1 to 5 identical or different halogen atoms, such as fluorine or chlorine atoms, or represents C 3 -C 6 -cycloalkyl which is optionally mono- to trisubstituted by identical or different substituents from the group consisting of C -C 4 -alkyl and halogen. 10 R 4 and R 5 independently of one another each represent hydrogen or represent the radicals -COR 6 , -COOR 7 or -S0 2 R 8 where R 6 , R 7 and R 8 independently of one another each represent CI-C 8 alkyl, CI-C 8 -halogenoalkyl having 1 to 5 identical or different 15 halogen atoms, such as fluorine, chlorine or bromine atoms CI C 4 -alkoxy-C-CS-alkyl, CI-C 4 -alkylthio-C-C 8 -alkyl, CI-C 4 alkylcarbonyloxy-C-C 8 -alkyl, CI-C 4 -alkoxycarbonyl-CI-C 8 alkyl; C 2 -C 8 -alkenyl, C 2 -C 8 -halogenoalkenyl having 1 to 5 identical or different halogen atoms, such as fluorine or 20 chlorine atoms; C 2 -C 8 -alkinyl, C 2 -C 8 -halogenoalkinyt having 1 to 5 identical or different halogen atoms, such as fluorine or chlorine atoms; represent C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkyl-C-C 4 -alkyl, C 3 C 6 -cycloalkyloxy-C-C 4 -alkyl or C 3 -C 6 -cycloalkylthio-CI-C 4 25 alkyl, each of which is optionally mono- to pentasubstituted (preferably mono- to trisubstituted) in the ring by identical or different substituents, suitable substituents being in each case halogen, CI-C 4 -alkyl, CI-C 4 -halogenoalkyl having 1 to 5 identical or different halogen atoms, such as fluorine or 30 chlorine atoms, CI-C 4 -alkoxy, CI-C 4 -halogenoalkoxy having 1 to 5 identical or different halogen atoms, such as fluorine or chlorine atoms, C 2 -C 4 -alkenyl, C 2 -C 4 -halogenoalkenyl having -67 1 to 5 identical or different halogen atoms, such as fluorine or chlorine atoms, nitro or cyano, represent phenyl, phenyl-C 1 -C 4 -alkyl, phenoxy-C 1 -C 4 -alkyl or phenylthio-Cl-C 4 -alkyl, each of which is optionally mono- to 5 pentasubstituted (preferably mono- to trisubstituted) in the ring by identical or different substituents, possible substituents being in each case halogen, nitro, cyano, CI-C 4 -alkyl, CI-C 4 halogenoalkyl having 1 to 5 identical or different halogen atoms, such as fluorine or chlorine atoms, CI-C 4 -alkoxy, Cl 10 C 4 -halogenoalkoxy having 1 to 5 identical or different halogen atoms, such as fluorine or chlorine atoms, CI-C 4 -alkylthio, CI C 4 -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 -halogenoalkenyl having 1 to 5 identical or 15 different halogen atoms, such as fluorine or chlorine atoms, C I-C 4 -alkoxycarbonyl or CI-C 4 -alkylcarbonyloxy, or represent a 5- or 6-membered heterocycle having 1 to 3 heteroatoms, preferably from the group consisting of nitrogen, sulphur and oxygen, which may optionally also contain CO 20 groups as ring members, and which is optionally mono- to trisubstituted by identical or different substituents. Examples include: o S N N 0 S N N H H I z z NNN N N N N N O S N N 0 S N N H I H 25 Z Z o S N N N , H I z -68 0 S NA A N N N N N N ,NN"O N N H N- N suitable substituents being in each case N halogen, nitro, cyano, Ci-C 4 -alkyl, CI-C 4 -alkoxy, Ci-C 4 alkylthio, C-C 4 -halogenoalkyl, C 1 -C 4 -halogenoalkoxy and 5 C 1 -C 4 -halogenoalkylthio. Additionally, suitable heterocycles may optionally be substituted at the ring nitrogen atom by a radical Z where Z represents C 1 -C 4 -alkyl (such as, in particular methyl or 10 ethyl), CI-C 4 -alkylcarbonyl (such as, in particular, methylcarbonyl or ethylcarbonyl), or represents phenylsulphonyl which is optionally mono- or disubstituted by identical or different substituents from the group consisting of Ci-C 4 -alkyl (such as, in 15 particular, methyl or ethyl), halogen (such as, in particular, fluorine or chlorine), Cl-C 4 -halogenoalkyl (such as, in particular, trifluoromethyl), CI-C4-alkoxy (such as, in particular, methoxy) and Cj-C 4 -halogeno alkoxy (such as, in particular, trifluoromethoxy); 20 suitable heterocycles are nitrogen-containing heterocycles in which at least one ring nitrogen does not carry a double bond and is consequently available for substitution; 25 XI and X 2 independently of one another each represent fluorine, chlorine, bromine, nitro, cyano, CI-C 4 -alkyl, CI-C 4 -alkoxy or CI-C4 halogenoalkyl having 1 to 5 identical or different halogen atoms, such as fluorine or chlorine atoms, - 69 m and n independently of one another each represent 0, 1 or 2, Y represents CI-C 6 -alkylene, Ci-C 6 -hydroxyalkylene, Ci-C 4 -alkoxy-C 1 C 6 -alkylene, C 1 -C 4 -alkylcarbonyloxy-Ci-C 6 -alkylene, cyano-CI-C 6 5 alkylene, Ci-C 4 -halogenoalkylene having 1 to 5 identical or different halogen atoms, such as fluorine or chlorine atoms, C 3 -C 6 -cycloalkyl CI-C 4 -alkylene which is optionally mono- to trisubstituted by identical or different substituents from the group consisting of fluorine, chlorine and methyl, represents C 2 -C 4 -alkenylene or CI-C4 10 alkylenoxy, halogen represents F, Cl, Br, I, in particular F, Cl, Br, particular emphasis being placed on F and Cl. 15 3. Compounds of the formula (I) according to Claim 1, in which Het represents one of the heterocycles R R 2 R o R N Ni or N.... S NI R N R where 20 RI represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl; CH 2 Cl, CH 2 Br, CHCICH 3 ; methoxy, ethoxy, methoxymethyl, ethoxymethyl; methylthiomethyl, methylthio or cyclopropyl, 25 R 2 represents hydrogen, chlorine, bromine, cyano, nitro, thio cyanato; methoxycarbonyl, ethoxycarbonyl, i-propoxycarbonyl, n-propoxycarbonyl; allyloxycarbonyl; methylthio, methylsulphinyl, methylsulphonyl or CSNH 2 ; or -70 RI and R2 together with the carbon atoms to which they are attached represent a carbocyclic 5- or 6-membered ring which is optionally mono- or disubstituted by identical or different substituents, suitable substituents being fluorine, chlorine, 5 methyl, ethyl, methoxy, trifluoromethoxy, nitro and cyano, R 3 represents hydrogen, methyl, ethyl, n- or i-propyl; methoxymethyl, ethoxymethyl, n-propoxymethyl, n-butoxymethyl; methylcarbonyl, methoxycarbonyl, ethoxycarbonyl, i-propoxycarbonyl, allyloxycar 10 bonyl, methylsulphonyl; phenylcarbonyl, phenoxycarbonyl or benzyl, each of which is optionally mono- or disubstituted in the phenyl ring by identical or different substituents from the group consisting of fluorine, chlorine, methyl and trifluoromethyl; or represents cyclopropyl, 15 R 4 and R 5 independently of one another each represent hydrogen or represent the radicals -COR 6 , -COOR 7 or -S0 2 R 8 , where R 6 , R 7 and R 8 independently of one another each represent CI-C 8 20 alkyl, C I-C 4 -halogenoalkyl having 1 to 5 identical or different halogen atoms, such as fluorine, chlorine or bromine atoms, C 1 -C 2 -alkoxy-C I-C 4 -alkyl, C I-C 2 -alkylthio-C I-C 4 -alkyl, C]-C 4 -alkylcarbonyloxy-Cl-C 4 -alkyl, C 1 -C 2 -alkoxycarbonyl CI-C 4 -alkyl; C 2 -C 4 -alkenyl, C 2 -C 4 -halogenoalkenyl having 1 25 to 5 identical or different halogen atoms, such as fluorine or chlorine atoms; C 2 -C 4 -alkinyl, C 2 -C 4 -halogenoalkinyl having I to 5 identical or different halogen atoms, such as fluorine or chlorine atoms; represent C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkyl-CI-C 2 -alkyl, C 3 30 C 6 -cycloalkyloxy-C-C 2 -alkyl and C 3 -C 6 -cycloalkylthio-C C 2 -alkyl, each of which is optionally mono- to trisubstituted in the ring by identical or different substitutents, possible - 71 substituents being in each case halogen, Ci-C 4 -alkyl, CI-C 2 halogenoalkyl having 1 to 5 identical or different halogen atoms, such as fluorine or chlorine atoms, CI-C 2 -alkoxy, C 1 C 2 -halogenoalkoxy having 1 to 5 identical or different halogen 5 atoms, such as fluorine or chlorine atoms, C 2 -C 4 -alkenyl, C 2 C 4 -halogenoalkenyl having 1 to 5 identical or different halogen atoms, such as fluorine or chlorine atoms, nitro or cyano, represent phenyl, phenyl-Cj-C 2 -alkyl, phenoxy-Ci-C 2 -alkyl or phenylthio-C-C 2 -alkyl, each of which is optionally mono- to 10 trisubstituted in the ring by identical or different substituents, possible substituents being in each case halogen, nitro, cyano, CI-C 2 -alkyl, CI-C 2 -halogenoalkyl having 1 to 5 identical or different halogen atoms, such as fluorine or chlorine atoms, CI-C 2 -alkoxy, C 1 -C 4 -halogenoalkoxy having 1 to 5 identical 15 or different halogen atoms, such as fluorine or chlorine atoms, C 1 -C 2 -alkylthio, Ci-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 -halogenoalkenyl having 1 to 5 identical or different halogen atoms, such as fluorine or 20 chlorine atoms, and also CI-C 2 -alkoxycarbonyl or CI-C2 alkylcarbonyloxy, or represent the heterocycles below, which are optionally mono- to trisubstituted by identical or different substituents: H I H I Z z N N N\ N N N PN rN 1qPN N > N 'N O S N N 0 S N N H I H 1 25 Z Z N-N N-N N-N N-N S N N N N H | z - 72 0 S O N N N, N N N H N Z N - possible substituents being in each case N fluorine, chlorine, bromine, nitro, cyano; methyl, ethyl, n- or i propyl, n-, i-, s- or t-butyl; methoxy, ethoxy, n- or i-propoxy; 5 methylthio; -CF 3 , -CHF 2 , -OCF 3 and -OCHF 2 , where Z represents CI-C 4 -alkyl, such as, in particular, methyl or 10 ethyl; C-C 4 -alkylcarbonyl, such as, in particular, methylcarbonyl or ethylcarbonyl; or represents phenylsulphonyl which is optionally mono- or disubstituted by identical or different substituents from the group consisting of CI-C 4 -alkyl, such as, in 15 particular, methyl or ethyl; halogen, such as, in particular, fluorine or chlorine; C 1 -C 4 -halogenoalkyl, such as, in particular, trifluoromethyl; CI-C 4 -alkoxy, such as, in particular, methoxy; and C 1 -C 4 halogenoalkoxy, such as, in particular, 20 trifluoromethoxy, XI and X 2 independently of one another each represent fluorine, chlorine, nitro, cyano, methyl, methoxy or trifluoromethyl, 25 m and n independently of one another each represent 0, 1 or 2, in particular 0 or 1, Y represents one of the radicals -CH 2 -, -CH(CH 3 )-, -CH(C 2 H 5 )-, -CH(n C 3 H7)-, -CH(i-C 3 H 7 )-, -CH 2 CH 2 -, -CH(OH)-, -CH(OCH 3 )-, -73 -CH(O-CO-CH 3 )-, -CH(CN)-, -CHF-, -CHCl-, -CH(--<])-, -CH=CH- or -CH 2 0-.

4. Compounds of the formula (I) according to Claim 1, in which 5 Het represents one of the heterocycles R R 2 R 2 RI N N ' RI R or R S S N R RI represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl; 10 CH 2 Cl, CH 2 Br, methoxy, ethoxy, methylthio or cyclopropyl, R 2 represents hydrogen, chlorine, bromine, cyano, nitro, methoxycarbonyl, ethoxycarbonyl, methylthio, methylsulphinyl or methylsulphonyl; or 15 RI 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 by identical or different substituents from the group consisting of fluorine, chlorine, methyl, nitro 20 and cyano, R 3 represents hydrogen, methyl, ethyl, methoxymethyl, ethoxymethyl, methylcarbonyl, methoxycarbonyl, ethoxycarbonyl, i-propoxy carbonyl, allyloxycarbonyl or phenoxycarbonyl, 25 R 4 and R 5 independently of one another each represent hydrogen or represent the radicals -COR 6 , -COOR 7 or -S0 2 R 8 where - 74 R 6 , R 7 and R 8 independently of one another each represent methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, n-pentyl, 2,2-di methylpropyl, n-hexyl, n-heptyl, n-octyl; represent 2-propenyl, 1-propenyl, 2-propinyl; 5 represent chloromethyl, 2-chloroethyl, trifluoromethyl, 2,2,2 trifluoroethyl; represent methoxymethyl, methoxyethyl, ethoxymethyl; represent cyclopropyl, cyclopentyl, cyclohexyl, cyclo propylmethyl, cyclopentylmethyl or cyclohexylmethyl, each of 10 which is optionally mono- to trisubstituted by identical or different substituents from the group consisting of methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, fluorine, chlorine, bromine and 2,2-dichlorovinyl, represent phenyl or benzyl, each of which is optionally mono 15 to trisubstituted by identical or different substituents from the group consisting of fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, methoxy, ethoxy, methylthio, trifluoromethyl, trifluoromethoxy, trifluoromethylthio, methoxycarbonyl, ethoxycarbonyl and methylcarbonyloxy, 20 or represent a heterocycle from the group consisting of 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; 1,2-oxazol-3-yl; 1,2-oxazol 4-yl; 1,2-oxazol-5-yl; 1,2-thiazol-3-yl; 1,2-thiazol-4-yl; 1,2 thiazol-5-yl; 3-pyrazolyl, 4-pyrazolyl, 5-pyrazolyl, 2-pyridyl, 3 25 pyridyl and 4-pyridyl, each of which is optionally mono- to trisubstituted by identical or different substituents, possible substituents being fluorine, chlorine, bromine, nitro, cyano, methyl, ethyl, methoxy, ethoxy or trifluoromethyl, 30 XI and X 2 independently of one another each represent fluorine, chlorine, cyano, methyl or trifluoromethyl, - 75 m and n independently of one another each represent 0 or 1, in particular 0, Y represents -CH 2 -, -CH(CH 3 )- or -CH 2 0-, in particular represents -CH2- or -CH(CH 3 )- 5

5. Process for preparing compounds of the formula (I) according to Claim 1, characterized in that a) nitro derivates of the formula (II) 10 NO Het CO ONO2 in which 15 Het, R 3 , X 1 , X 2 , Y, m and n are each as defined in Claim 1, are reduced with base metals in acidic solution or by catalytic hydrogenation, if appropriate in the presence of a diluent, and 20 b) the resulting amino derivatives of the formula (I-1) NH Het. I-CO' ONH (I1), Ra3 X in which 25 Het, R 3 , X 1 , X 2 , Y, m and n are each as defined in Claim 1, - 76 are, if appropriate, reacted with compounds of the formula (III) G-R(II), 5 in which R 4 - 1 has the meanings of R 4 , except for hydrogen, and 10 G represents a leaving group, if appropriate in the presence of a base and if appropriate in the presence of a diluent; 15 or c) aminoheterocycles of the formula (IV) Het H N (IV), R 20 in which Het and R 3 are each as defined in Claim 1, 25 are reacted with compounds of the formula (V) N4-1 R COI O -? Xn - 77 in which G, R 4 - 1 , R 5 , X1, X 2 , Y, m and n are each as defined above, 5 if appropriate in the presence of a base and if appropriate in the presence of a diluent.

6. Compounds of the formula (V) 10 NR - R G C O O Xm in which 15 G, R 5 , Xl, X 2 , Y, m and n are each as defined in Claim I and R 4 - 1 has the meaning of R 4 given in Claim 1, except for hydrogen.

7. Compounds of the formula (VI) 20 NR4-R HO C O O (VI), in which 25 R 5 , XI, X 2 , Y, m and n are each as defined in Claim 1 and - 78 R 4 - 1 has the meaning of R 4 given in Claim 1, except for hydrogen.

8. Pesticides or fungicides, characterized in that they comprise a compound of the formula (I) according to Claim 1. 5

9. Use of compounds of the formula (1) according to Claim 1 for controlling pests and fungi.

10. Method for controlling pests and fungi, characterized in that compounds of 10 the formula (I) according to Claim 1 are allowed to act on pests or fungi and/or their habitat.

11. Process for preparing pesticides and fungicides, characterized in that compounds of formula (I) according to Claim 1 are mixed with extenders 15 and/or surfactants.