# US 2010/0167922 A1 · 3-Amino-1,2-benzisothiazole Compounds for Combating Animal Pest

> Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt

- Number: US 2010/0167922 A1
- Document ID: US20100167922A1
- Status: Published application
- Kind: A1
- Application number: 12/294,753
- Filed: 2007-03-22
- Published: 2010-07-01
- Earliest claimed: 2006-03-31
- Assignees: BASF SE
- Inventors: Matthias Pohlman; Wolfgang von Deyn; Florian Kaiser; Ernst Baumann; Michael Rack; Douglas D. Anspaugh; Deborah L. Culbertson; Henry Van Tuyl Cotter
- Web page: https://patentgrep.com/patent/US20100167922A1

## CPC

- C07D 417/06: linked by a carbon chain containing only aliphatic carbon atoms
- A01N 43/80: five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2
- A61P 33/14: Ectoparasiticides, e.g. scabicides
- C07D 275/04: condensed with carbocyclic rings or ring systems
- C07D 275/06: with hetero atoms directly attached to the ring sulfur atom
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- A01N: PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF (preservation of food or foodstuff A23); BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES (preparations for medical, dental or toiletry purposes which kill or prevent the growth or proliferation of unwanted organisms A61K); PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS

## Abstract

The present invention relates to 3-amino-1,2-benzisothiazole compounds of formula I wherein R1, R2, R3, R4, R5 and n are defined in the description. The present invention relates to insecticidal compounds of formula I and to their isomeric imino derivatives, as well as to the enantiomers, diastereomers and salts thereof and to compositions comprising such compounds. The invention also relates to the use of the 3-amino-1,2-benzisothiazole compounds, of their salts or of compositions comprising them for combating animal pests. Furthermore the invention relates also to methods of applying such compounds.

## Claims

### Claim at position 1

1-15. (canceled)

### Claim 16

3-amino-1,2-benzisothiazole compounds of formula I
wherein
n is 0;
R1 is selected from C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C3-C8-cycloalkyl, C3-C6-halocycloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, wherein the mentioned radicals may be unsubstituted or may carry 1, 2 or 3 radicals, selected from the group consisting of cyano, nitro, amino, C1-C4-alkoxy, C1-C4-alkylthio, C1-C4-alkylsulfinyl, C1-C4-alkylsulfonyl, C1-C4-haloalkoxy, C1-C4-haloalkylthio, (C1-C4-alkoxy)carbonyl, (C1-C4-alkyl)amino, di(C1-C4-alkyl)amino, aminocarbonyl, (C1-C4-alkyl)aminocarbonyl, di(C1-C4-alkyl)aminocarbonyl, C3-C8-cycloalkyl and phenyl, it being possible for phenyl to be unsubstituted, partially or fully halogenated and/or to carry 1, 2 or 3 substituents, independently of one another selected from the group consisting of CN, C1-C4-haloalkyl, C1-C4 alkoxy and C1-C4-haloalkoxy and
R2, R3 and R4 are independently of one another selected from the group consisting of hydrogen, halogen, cyano, azido, nitro, C1-C6-alkyl, C3-C8-cycloalkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-alkylthio, C1-C4-alkylsulfinyl, C1-C4-alkylsulfonyl, C1-C4-haloalkoxy, C1-C4-haloalkylthio, C2-C6-alkenyl, C2-C6-alkynyl, (C1-C4-alkoxy)carbonyl, amino, (C1-C4-alkyl)amino, di(C1-C4-alkyl)amino, aminocarbonyl, (C1-C4-alkyl)aminocarbonyl, di(C1-C4-alkyl)aminocarbonyl, sulfonyl, sulfonylamino, sulfenylamino, sulfanylamino and C(═O)—R2a or C(═O)—R3a or C(═O)—R4a, and wherein,
R2a or R3a or R4a are selected from the group consisting of hydrogen, hydroxy, C1-C6-alkoxy, amino, C1-C6-alkyl, aryl, aryl-C1-C6-alkyl, (C1-C6-alkyl)-amino, di-(C1-C6-alkyl)-amino, 3- to 7-membered heteroaryl or heteroaryl-C1-C4-alkyl, wherein the heteroaryl ring contains as ring members 1, 2 or 3 heteroatoms, selected from the group consisting of nitrogen, oxygen, sulfur, a group SO, SO2 or NR2b or NR3b or NR4b, and wherein R2b or R3b or R4b are hydrogen, C1-C6-alkyl or (C1-C6-alkyl)-carbonyl;
R5 is selected from the group consisting of hydrogen, OR5a, C2-C10-alkenyl, C2-C10-alkinyl, C3-C10-cycloalkyl, aryl-C1-C4-alkyl, hetaryl-C1-C4-alkyl, heterocyclyl-C1-C4-alkyl, wherein these radicals may be unsubstituted, partially or fully halogenated and/or may carry 1-4 radicals selected from the group consisting of C1-C10-alkoxy, C1-C10-alkylthio, C1-C10-alkylsulfinyl, C1-C10-alkylsulfonyl, C1-C10-haloalkoxy, C1-C10-haloalkylthio, (C1-C10-alkoxy)carbonyl, cyano, nitro, amino, (C1-C10-alkylamino, di-(C1-C10-alkyl)amino, C3-C10-cycloalkyl and phenyl, it being possible for phenyl to be unsubstituted, partially or fully halogenated and/or to carry 1-3 substituents selected from the group consisting of CN, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, and wherein
R5a is selected from hydrogen, C1-C10-alkyl, C1-C10-acyl, C3-C10-cycloalkyl, C2-C10-alkenyl, C2-C10-alkynyl, aryl, aryl-C1-C4-alkyl, heteroaryl and heteroaryl-C1-C4-alkyl, heterocyclyl or heterocyclyl-C1-C4-alkyl and wherein all radicals may be unsubstituted, partially or fully halogenated and/or may carry 1, 2 or 3 radicals, selected from the group consisting of cyano, nitro, amino, C1-C4-alkoxy, C1-C4-alkylthio, C1-C4-alkylsulfinyl, C1-C4-alkylsulfonyl, C1-C4-haloalkoxy, C1-C4-haloalkylthio, (C1-C4-alkoxy)carbonyl, (C1-C4-alkyl)amino, di(C1-C4-alkyl)amino and C3-C8-cycloalkyl;
or the enantiomers, distereomers or salts thereof;
with the proviso
that if n is 0, R5 is not hydrogen and
that the 3-amino-1,2-benzisothiazole compound of formula I is not 4-Methoxy-N-(2-methyl-2-phenylpropyl)benzo[d]isothiazol-3-amine, not 4-Methoxy-N-(2-methyl-2-(6-methylpyridin-2-yl)propyl)benzo[d]isothiazol-3-amine or not N1-(4-Methylbenzo[d]isothiazol-3-yl)propane-1,3-diamine.

### Claim 17 (depends on 16)

3-amino-1,2 benzisothiazole compounds of formula I according to claim 16, wherein R1 is selected from C1-C6-alkoxy or C1-C6-haloalkoxy.

### Claim 18 (depends on 16)

3-amino-1,2 benzisothiazole compounds of formula I according to claim 16, wherein R1 is selected from C1-C6-fluoroalkoxy or C1-C6-chloroalkoxy.

### Claim 19 (depends on 16)

3-amino-1,2 benzisothiazole compounds of formula I according to claim 16, wherein R2, R3 and R4 are independently of one another selected from the group consisting of hydrogen, F, Cl, Br or J.

### Claim 20 (depends on 16)

3-amino-1,2 benzisothiazole compounds of formula I according to claim 16, wherein R2, R3 and R4 are independently of one another hydrogen or fluoro.

### Claim 21 (depends on 16)

3-amino-1,2 benzisothiazole compounds of formula I according to claim 16, wherein R2, R3 and R4 are hydrogen.

### Claim 22 (depends on 16)

3-amino-1,2 benzisothiazole compounds of formula I according to claim 16, wherein:
R5 is selected from C1-C6-alkyl, which may be unsubstituted, partially or fully halogenated and/or may carry 1-4 radicals selected from the group consisting of C1-C10-alkoxy, C1-C10-alkylthio, C1-C10-alkylsulfinyl, C1-C10-alkylsulfonyl, C1-C10-haloalkoxy, C1-C10-haloalkylthio, (C1-C10-alkoxy)carbonyl, cyano, nitro, amino, (C1-C10-alkyl)amino, di-(C1-C10-alkyl)amino, C3-C10-cycloalkyl and phenyl, it being possible for phenyl to be unsubstituted, partially or fully halogenated and/or to carry 1-3 substituents selected from the group consisting of CN, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy.

### Claim 23 (depends on 16)

3-amino-1,2 benzisothiazole compounds of formula I according to claim 16, wherein:
R1 is selected from C1-C6-alkoxy or C1-C6-haloalkoxy and
R2, R3 and R4 are independently of one another selected from the group consisting of hydrogen, F, Cl, Br or J.

### Claim 24 (depends on 16)

3-amino-1,2 benzisothiazole compounds of formula I according to claim 16, wherein:
R1 is selected from C1-C6-alkoxy or C1-C6-haloalkoxy and
R2, R3 and R4 are hydrogen.

### Claim 25 (depends on 16)

3-amino-1,2 benzisothiazole compounds of formula I according to claim 16, wherein:
R1 is selected from C1-C6-alkoxy or C1-C6-haloalkoxy;
R2, R3 and R4 are independently of one another selected from the group consisting of hydrogen, F, Cl, Br or J; and
R5 is selected from C1-C6-alkyl, which may be unsubstituted, partially or fully halogenated and/or may carry 1-4 radicals selected from the group consisting of C1-C10-alkoxy, C1-C10-alkylthio, C1-C10-alkylsulfinyl, C1-C10-alkylsulfonyl, C1-C10-haloalkoxy, C1-C10-haloalkylthio, (C1-C10-alkoxy)carbonyl, cyano, nitro, amino, (C1-C10-alkyl)amino, di-(C1-C10-alkyl)amino, C3-C10-cycloalkyl and phenyl, it being possible for phenyl to be unsubstituted, partially or fully halogenated and/or to carry 1-3 substituents selected from the group consisting of CN, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy.

### Claim 26 (depends on 16)

A composition comprising at least one 3-amino-1,2-benzisothiazole compound of the formula I according to claim 16, or the enantiomer, diastereomer or salt thereof and at least one inert liquid and/or solid carrier.

### Claim 27 (depends on 16)

A method for combating or controlling animal pests comprising contacting the animal pests or their food supply, habitat or breeding grounds with a pesticidally effective amount of at least one 3-amino-1,2-benzisothiazole compound of the formula I according to claim 16, or the enantiomers, diastereomers or salts thereof.

### Claim 28 (depends on 16)

A method for protecting growing plants from attack or infestation by animal pests comprising contacting a plant, or soil or water in which the plant is growing, with a pesticidally effective amount of at least one 3-amino-1,2-benzisothiazole compound of the formula I according to claim 16, or the enantiomers, diastereomers or salts thereof.

### Claim 29 (depends on 16)

A method for the protection of seeds from soil insects and of the seedlings' roots and shoots from soil and foliar insects comprising contacting the seeds before sowing and/or after pregermination with at least one 3-amino-1,2-benzisothiazole compound of the formula I according to claim 16, or the enantiomers, diastereomers or salts thereof.

### Claim 30 (depends on 16)

Seed comprising an 3-amino-1,2-benzisothiazole compound of the formula I as defined in claim 16, or the enantiomer, diastereomer or agriculturally acceptable salt thereof, in an amount of from 0.1 g to 10 kg per 100 kg of seed.

### Claim 31 (depends on 23)

A composition comprising at least one 3-amino-1,2-benzisothiazole compound of the formula I according to claim 23, or the enantiomer, diastereomer or salt thereof and at least one inert liquid and/or solid carrier.

### Claim 32 (depends on 23)

A method for combating or controlling animal pests comprising contacting the animal pests or their food supply, habitat or breeding grounds with a pesticidally effective amount of at least one 3-amino-1,2-benzisothiazole compound of the formula I according to claim 23, or the enantiomers, diastereomers or salts thereof.

### Claim 33 (depends on 23)

A method for protecting growing plants from attack or infestation by animal pests comprising contacting a plant, or soil or water in which the plant is growing, with a pesticidally effective amount of at least one 3-amino-1,2-benzisothiazole compound of the formula I according to claim 23, or the enantiomers, diastereomers or salts thereof.

### Claim 34 (depends on 23)

A method for the protection of seeds from soil insects and of the seedlings' roots and shoots from soil and foliar insects comprising contacting the seeds before sowing and/or after pregermination with at least one 3-amino-1,2-benzisothiazole compound of the formula I according to claim 23, or the enantiomers, diastereomers or salts thereof.

### Claim 35 (depends on 23)

Seed comprising an 3-amino-1,2-benzisothiazole compound of the formula I as defined in claim 23, or the enantiomer, diastereomer or agriculturally acceptable salt thereof, in an amount of from 0.1 g to 10 kg per 100 kg of seed.