# US 8,772,289 B2 · N-Thio-anthranilamid compounds and their use as pesticides

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

- Number: US 8,772,289 B2
- Document ID: US8772289B2
- Status: Granted
- Kind: B2
- Application number: 13/682,246
- Filed: 2012-11-20
- Published: 2013-03-28
- Granted: 2014-07-08
- Earliest claimed: 2005-07-07
- Assignees: BASF SE
- Applicants: BASF SE
- Inventors: Thomas Schmidt; Michael Puhl; Joachim Dickhaut; Henricus Maria Martinus Bastiaans; Michael Rack; Deborah L. Culbertson; Douglas D. Anspaugh; Franz-Josef Braun; Toni Bucci; Henry Van Tuyl Cotter; David G. Kuhn; Hassan Oloumi-Sadeghi
- Web page: https://patentgrep.com/patent/US8772289B2

## CPC

- C07D 401/04: directly linked by a ring-member-to-ring-member bond
- A01N 43/56: 1,2-Diazoles; Hydrogenated 1,2-diazoles
- A01N 43/84: six-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,4
- A61P 33/00: Antiparasitic agents
- C07D 401/14: containing three or more hetero rings
- C07D 409/14: containing three or more hetero rings
- C07D 413/14: containing three or more hetero rings
- 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

N-Thio-anthranilamid compounds of formula (I) wherein A is A1 wherein the variables and the indices are as defined per the description, processes for preparing the compounds I, pesticidal compositions comprising compounds I, use of compounds I for the control of insects, acarids or nematodes, and methods for treating, controlling, preventing or protecting animals against infestation or infection by parasites by use of compounds of formula I.

## Claims

### Claim 1

A compound of formula I having the following structure,
wherein,
R1 is hydrogen; or C1-C10-alkyl, C2-C10-alkenyl, C2-C10-alkynyl, or C3-C8-cycloalkyl, each of which is unsubstituted or substituted with 1 to 5 groups independently selected from halogen, cyano, nitro, hydroxy, C1-C10-alkoxy, C1-C10-alkylthio, C1-C10-alkylsulfonyl, C2-C10-alkoxycarbonyl, C1-C10-alkylamino, di(C1-C10-alkyl)amino and C3-C8-cycloalkylamino; or C1-C10-alkylcarbonyl, C1-C10-alkoxycarbonyl C1-C10-alkylaminocarbonyl, di(C1-C10-alkyl)aminocarbonyl;
A is a group selected from A1
wherein, # denotes the binding site, and
R2 and R3 each independently are R6, —C(=G)R7, —C(═NOR7)R7, —C(═NNR72)R7, —C(=G)OR7, —C(=G)NR72, —OC(=G)R7, —OC(=G)OR7, —NR7C(=G)R7, —N[C(=G)R7]2, —NR7C(=G)OR7, —C(=G)NR7—NR72, —C(=G)NR7—NR7[C(=G)R7], —NR7—C(=G)NR72, —NR7—NR7C(=G)R7, —NR7—N[C(=G)]2, —N[(C=G)R7]—NR72, —NR7—NR7[(C=G)GR7], —NR7[(C=G)NR72, —NR7[C═NR7]R7, —NR7(C═NR7)NR72, —O—NR72, —O—NR7(C=G)R7, —SO2NR72, —NR7SO2R7, —SO2OR7, —OSO2R7, —NR72, —SR7, —SiR73, —PR72, —P(=G)R7, —SOR7, —SO2R7, —PG2R72, or —PG3R72; or
R2 and R3 together with the sulfur atom to which they are attached form a saturated, partially unsaturated or unsaturated 3- to 8-membered ring which contains 1 to 4 heteroatoms selected from oxygen, nitrogen, sulfur, which ring can be fused with one or two saturated, partially unsaturated or unsaturated 5- to 6-membered rings which may contain 1 to 4 heteroatoms selected from oxygen, nitrogen, sulfur, wherein all of the above rings are unsubstituted or substituted by any combination of 1 to 6 groups R8;
G is oxygen or sulfur;
R6 is C1-C20-alkyl, C2-C20-alkenyl, C2-C20-alkynyl, C3-C8-cycloalkyl, C3-C8-cycloalkenyl, C3-C8-cycloalkynyl, phenyl, naphthyl, biphenyl, or a saturated, partially unsaturated or unsaturated 3- to 8-membered ring system which contains 1 to 4 heteroatoms selected from oxygen, nitrogen, sulfur, wherein all of these groups are unsubstituted or substituted by any combination of 1 to 6 groups R8;
R7 is hydrogen or R6;
R8 is R9; or two groups R8 together with the atoms to which they are attached form a saturated, partially unsaturated or unsaturated 3- to 8-membered ring system which may contain 1 to 4 heteroatoms/heterogroups selected from oxygen, nitrogen, sulfur, SO and SO2, and which ring system is unsubstituted or substituted with any combination of 1 to 6 groups R9;
R9 is R10, R11, —C(=G)R10, —C(═NOR10)R10, —C(═NNR102)R10, —(C(=G)OR10, —C(=G)NR102, —OC(=G)R10, —OC(=G)OR10, —NR10C(=G)R10, —N[C(=G)R10]2, —NR10C(=G)OR10, —C(=G)NR10—NR102, —C(=G)NR10—NR10[C(=G)R10], —NR10—C(=G)NR102, —NR10—NR10C(=G)R10, —NR10—N[C(=G)R10]2, —N[(C=G)R10]—NR102, —NR10—NR10[(C=G)GR10], —NR10[(C=G)NR102, —NR10[C═NR10]R10, —NR10(C═NR10NR102, —O—NR102, —O—NR10(C=G)R10, —SO2NR102, —NR10SO2R10, —SO2OR10, —OSO2R10, —OR10, —NR102, —SR10, —SiR102, —P(=G)R10, —SOR10, —SO2R10, —PG2R102, —PG3R102, or two groups R9 together are (=G), (═N—R10), (═CR102), (═CHR10, or (═CH2);
R10 is C1-C10-alkyl, C2-C10-alkenyl, C2-C10-alkynyl, C3-C8-cycloalkyl, C4-C8-cycloalkenyl, C3-C8-cycloalkyl-C4-C8-cycloalkenyl-C1-C4-alkyl, C3-C8-cycloalkyl-C2-C4-alkenyl, C4-C8-cycloalkenyl-C2-C4-alkenyl, C1-C10-alkyl-C3-C8-cycloalkyl, C2-C10-alkenyl-C3-C8-cycloalkyl, C2-C10-alkynyl-C3-C8-cycloalkyl, C1-C10-alkyl-C4-C8-cycloalkenyl, C2-C10-alkenyl-C4-C8-cycloalkenyl, C2-C10-alkynyl-C4-C8-cycloalkenyl, a saturated, partially unsaturated or unsaturated 3- to 8-membered ring system which contains 1 to 4 heteroatoms selected from oxygen, nitrogen, sulfur;
wherein the above groups are unsubstituted or substituted with any combination of from 1 to 6 groups R11;
R11 is halogen, cyano, nitro, hydroxy, mercapto, amino, formyl, C1-C10-alkylcarbonyl, C1-C10-alkoxy, C2-C10-alkenyloxy, C2-C10-alkynyloxy, C1-C10-haloalkoxy, C3-C10-haloalkenyloxy, C3-C10-haloalkynyloxy, C3-C8-cycloalkoxy, C4-C8-cycloalkenyloxy, C3-C8-halocycloalkoxy, C4-C8-halocycloalkenyloxy, C3-C8-cycloalkyl-C1-C4-alkoxy, C4-C8-cycloalkenyl-C1-C4-alkoxy, C3-C8-cycloalkyl-C2-C4-alkenyloxy, C4-C8-cycloalkenyl-C2-C4-alkenyloxy, C1-C10-alkyl-C3-C8-cycloalkoxy, C1-C10-alkenyl-C3-C8-cycloalkoxy, C1-C10-alkynyl-C3-C8-cycloalkoxy, C1-C10-alkyl-C3-C8-cycloalkenyloxy, C1-C10-alkenyl-C3-C8-cycloalkenyloxy, C1-C4-alkoxy-C1-C10-alkoxy, C1-C4-alkoxy-C2-C10-alkenyloxy, mono- or di(C1-C10-alkyl)carbamoyl, mono- or di(C1-C10-haloalkyl)carbamoyl, mono- or di(C3-C8-cycloalkyl)carbamoyl, C1-C10-alkoxycarbonyl, C3-C8-cycloalkoxycarbonyl, C1-C10-alkylcarbonyloxy, C3-C8-cyclo alkylcarbonyloxy, C1-C10-haloalkoxycarbonyl, C1-C10-haloalkylcarbonyloxy, C1-C10-alkanamido, C1-C10-haloalkanamido, C2-C10-alkenamido, C3-C8-cycloalkanamido, C3-C8-cycloalkyl-C1-C4-alkanamido, C1-C10-alkylthio, C2-C10-alkenylthio, C2-C10-alkynylthio, C1-C10-haloalkylthio, C2-C10-haloalkenylthio, C2-C10-haloalkynylthio, C3-C8-cycloalkylthio, C3-C8-cycloalkenylthio, C3-C8-halocycloalkylthio, C3-C8-halocycloalkenylthio, C3-C8-cycloalkyl-C1-C4-alkylthio, C4-C8-cycloalkenyl-C1-C4-alkylthio, C3-C8-cycloalkyl-C2-C4-alkenylthio, C4-C8-cycloalkenyl-C2-C4-alkenylthio, C1-C10-alkyl-C3-C8-cycloalkylthio, C1-C10-alkenyl-C3-C8-cycloalkylthio, C1-C10-alkynyl-C3-C8-cycloalkylthio, C1-C10-alkyl-C3-C8-cycloalkenylthio, C1-C10-alkenyl-C3-C8-cycloalkenylthio, C1-C10-alkylsulfinyl, C2-C10-alkenylsulfinyl, C2-C10-alkynylsulfinyl, C1-C10-haloalkylsulfinyl, C2-C10-haloalkenylsulfinyl, C2-C10-haloalkynylsulfinyl, C3-C8-cycloalkylsulfinyl, C3-C8-cycloalkenylsulfinyl, C3-C8-halocycloalkylsulfinyl, C3-C8-halocycloalkenylsulfinyl, C3-C8-cycloalkyl-C1-C4-alkylsulfinyl, C4-C8-cycloalkenyl-C1-C4-alkylsulfinyl, C3-C8-cycloalkyl-C2-C4-alkenylsulfinyl, C4-C8-cycloalkenyl-C2-C4-alkenylsulfinyl, C1-C10-alkyl-C3-C8-cycloalkylsulfinyl, C1-C10-alkenyl-C3-C8-cycloalkylsulfinyl, C1-C10-alkynyl-C3-C8-cycloalkylsulfinyl, C1-C10-alkyl-C3-C8-cycloalkenylsulfinyl, C1-C10-alkenyl-C3-C8-cycloalkenylsulfinyl, C1-C10-alkylsulfonyl, C2-C10-alkenylsulfonyl, C2-C10-alkynylsulfonyl, C1-C10-haloalkylsulfonyl, C2-C10-haloalkenylsulfonyl, C2-C10-haloalkynylsulfonyl, C3-C8-cycloalkylsulfonyl, C3-C8-cycloalkenylsulfonyl, C3-C8-halocycloalkylsulfonyl, C3-C8-halocycloalkenylsulfonyl, C3-C8-cycloalkyl-C1-C4-alkylsulfonyl, C4-C8-cycloalkenyl-C1-C4-alkylsulfonyl, C3-C8-cycloalkyl-C2-C4-alkenylsulfonyl, C4-C8-cycloalkenyl-C2-C4-alkenylsulfonyl, C1-C10-alkyl-C3-C8-cycloalkylsulfonyl, C1-C10-alkenyl-C3-C8-cycloalkylsulfonyl, C1-C10-alkynyl-C3-C8-cycloalkylsulfonyl, C1-C10-alkyl-C3-C8-cycloalkenylsulfonyl, C1-C10-alkenyl-C3-C8-cycloalkenylsulfonyl, di(C1-C10-alkyl)amino, C1-C10-alkylamino, C2-C10-alkenylamino, C2-C10-alkynylamino, C1-C10-alkyl-C2-C10-alkenylamino, C1-C10-alkyl-C2-C10-alkynylamino, C1-C10-haloalkylamino, C2-C10-haloalkenylamino, C2-C10-haloalkynylamino, C3-C8-cycloalkylamino, C3-C8-cycloalkenylamino, C3-C8-halocycloalkylamino, C3-C8-halocycloalkenylamino, C3-C8-cycloalkyl-C1-C4-alkylamino, C4-C8-cycloalkenyl-C1-C4-alkylamino, C3-C8-cycloalkyl-C2-C4-alkenylamino, C4-C8-cycloalkenyl-C2-C4-alkenylamino, C1-C10-alkyl-C3-C8-cycloalkylamino, C1-C10-alkenyl-C3-C8-cycloalkylamino, C1-C10-alkynyl-C3-C8-cycloalkylamino, C1-C10-alkyl-C3-C8-cycloalkenylamino, C1-C10-alkenyl-C3-C8-cycloalkenylamino, tri(C1-C10-alkyl)silyl, aryl, aryloxy, arylthio, arylamino, aryl-C1-C4-alkoxy, aryl-C3-C4-alkenyloxy, aryl-C1-C4-alkylthio, aryl-C2-C4-alkenylthio, aryl-C1-C4-alkylamino, aryl-C3-C4-alkenylamino, triarylsilyl,
wherein aryl is phenyl, naphthyl or biphenyl, or a saturated, partially unsaturated or unsaturated 3- to 8-membered ring system which contains 1 to 4 heteroatoms selected from oxygen, nitrogen, sulfur, wherein said aryl and heteroatom cyclic ringsystems are unsubstituted or substituted with any combination of from 1 to 6 groups selected from halogen, cyano, nitro, amino, hydroxy, mercapto, C1-C4-alkyl, C1-C4-haloalkyl, C3-C8-cycloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-alkylthio, C1-C4-haloalkylthio, di(C1-C4-alkyl)amino, C1-C4-alkylamino, C1-C4-haloalkylamino, formyl and C1-C4-alkylcarbonyl;
Q1 is hydrogen, halogen, cyano, SCN, nitro, hydroxy, C1-C10-alkyl, C1-C10-haloalkyl, C3-C8-cycloalkyl, C1-C10-alkoxy, C1-C10-haloalkoxy, C1-C10-alkylthio, C1-C10-haloalkylthio, C1-C10-alkylsulfonyl, C1-C10-alkylsulfonyloxy, C1-C10-alkylamino or di(C1-C10-alkyl)amino, most preferably hydrogen, halogen, cyano, C1-C4-alkyl or C1-C4-haloalkyl;
Q2 is halogen, cyano, SCN, nitro, hydroxy, C1-C10-haloalkyl, C3-C8-cycloalkyl, C1-C10-alkoxy, C1-C10-haloalkoxy, C1-C10-alkylthio, C1-C10-haloalkylthio, C1-C10-alkylsulfonyl, C1-C10-alkylsulfonyloxy, C1-C10-alkylamino or di(C1-C10-alkyl)amino, most preferably halogen, cyano, C1-C4-alkyl or C1-C4-haloalkyl;
Q3 is halogen, C1-C10-alkyl, C1-C10-haloalkyl, C2-C10-alkynyl, C3-C8-cycloalkyl, C3-C8-halocycloalkyl, each unsubstituted or independently substituted with 1 to 2 groups selected from cyano, C1-C10-alkoxy, C1-C10-haloalkoxy or C1-C1-alkylthio;
Q4 is halogen, cyano, nitro, C1-C10-alkyl, C1-C10-haloalkyl, C1-C10-alkoxy, C1-C10-haloalkoxy, C1-C10-alkylthio, C1-C10-haloalkylthio, C1-C10-alkylsulfonyl, C1-C10-haloalkylsulfonyl, or C1-C10-alkoxycarbonyl, preferably halogen or C1-C4-haloalkyl;
X and Y are oxygen;
W is N or CQ4;
n is 0 or 1;
V and V′ each independently are N or CH; and
p is 0, 1, 2, 3, or 4;
or the enantiomers or salts or N-oxides thereof.

### Claim 2 (depends on 1)

The compound of claim 1, where R2 and R3 each independently are phenyl, C1-C6-alkyl, C2-C6-alkenyl, or C2-C6-alkynyl, which are unsubstituted or substituted with any combination of 1 to 6 groups selected from halogen and cyano.

### Claim 3 (depends on 1)

The compound of claim 1, where R2 and R3 each independently are C1-C4-alkyl, phenylmethyl, allylmethyl, propargylmethyl, or together with the sulfur atom to which they are attached form a 3- to 6-membered saturated ring which contains 1 to 3 heteroatoms selected from sulfur and oxygen.

### Claim 4 (depends on 1)

The compound of claim 1, wherein Q1 is hydrogen, halogen, cyano, C1-C4-alkyl, or C1-C4-haloalkyl.

### Claim 5 (depends on 4)

The compound of claim 4, wherein Q1 is halogen or cyano.

### Claim 6 (depends on 1)

The compound of claim 1, wherein Q2 is halogen, cyano, C1-C4-alkyl, or C1-C4-haloalkyl.

### Claim 7 (depends on 1)

The compound of claim 1, wherein Q3 is halogen, C1-C4-haloalkyl, or C1-C4-haloalkoxy.

### Claim 8 (depends on 7)

The compound of claim 7, wherein Q3 is C1-C4-haloalkyl.

### Claim 9 (depends on 1)

The compound of claim 1, wherein Q4 is halogen or C1-C4-haloalkyl and is in the ortho-position.

### Claim 10 (depends on 1)

The compound of claim 1, wherein Q4 is halogen.

### Claim 11 (depends on 1)

A method for controlling insects, acarids or nematodes comprising, contacting said insect, acarid or nematode or their food supply, habitat, breeding ground or their locus with a pesticidally effective amount of one or more compounds of claim 1.

### Claim 12 (depends on 11)

The method of claim 11, where R2 and R3 each independently are phenyl, C1-C6-alkyl, C2-C6-alkenyl, or C2-C6-alkynyl, which are unsubstituted or substituted with any combination of 1 to 6 groups selected from halogen and cyano.

### Claim 13 (depends on 11)

The method of claim 11, where R2 and R3 each independently are C1-C4-alkyl, phenylmethyl, allylmethyl, propargylmethyl, or together with the sulfur atom to which they are attached form a 3- to 6-membered saturated ring which contains 1 to 3 heteroatoms selected from sulfur and oxygen.

### Claim 14 (depends on 11)

The method of claim 11, wherein Q1 is hydrogen, halogen, cyano, C1-C4-alkyl, or C1-C4-haloalkyl.

### Claim 15 (depends on 14)

The method of claim 14, wherein Q1 is halogen or cyano.

### Claim 16 (depends on 11)

The method of claim 11, wherein Q2 is halogen, cyano, C1-C1-alkyl, or C1-C4-haloalkyl.

### Claim 17 (depends on 11)

The method of claim 11, wherein Q3 is halogen, C1-C4-haloalkyl, or C1-C4-haloalkoxy.

### Claim 18 (depends on 17)

The method of claim 17, wherein Q3 is C1-C4-haloalkyl.

### Claim 19 (depends on 11)

The method of claim 11, wherein Q4 is halogen or C1-C4-haloalkyl and is in the ortho-position.

### Claim 20 (depends on 11)

The method of claim 11, wherein Q4 is halogen.

### Claim 21 (depends on 1)

A method of protecting growing plants from attack or infestation by insects, acarids or nematodes comprising, applying to the foliage of the plants, or to the soil or water in which said plants are growing a pesticidally effective amount of one or more compounds of claim 1.

### Claim 22 (depends on 21)

The method of claim 21, where R2 and R3 each independently are phenyl, C1-C6-alkyl, C2-C6-alkenyl, or C2-C6-alkynyl, which are unsubstituted or substituted with any combination of 1 to 6 groups selected from halogen and cyano.

### Claim 23 (depends on 21)

The method of claim 21, where R2 and R3 each independently are C1-C4-alkyl, phenylmethyl, allylmethyl, propargylmethyl, or together with the sulfur atom to which they are attached form a 3- to 6-membered saturated ring which contains 1 to 3 heteroatoms selected from sulfur and oxygen.

### Claim 24 (depends on 21)

The method of claim 21, wherein Q1 is hydrogen, halogen, cyano, C1-C4-alkyl, or C1-C4-haloalkyl.

### Claim 25 (depends on 24)

The method of claim 24, wherein Q1 is halogen or cyano.

### Claim 26 (depends on 21)

The method of claim 21, wherein Q2 is halogen, cyano, C1-C4-alkyl, or C1-C4-haloalkyl.

### Claim 27 (depends on 21)

The method of claim 21, wherein Q3 is halogen, C1-C4-haloalkyl, or C1-C4-haloalkoxy.

### Claim 28 (depends on 27)

The method of claim 27, wherein Q3 is C1-C4-haloalkyl.

### Claim 29 (depends on 21)

The method of claim 21, wherein Q4 is halogen or C1-C4-haloalkyl and is in the ortho-position.

### Claim 30 (depends on 21)

The method of claim 21, wherein Q4 is halogen.

### Claim 31 (depends on 1)

A method for treating an animal infected by parasites or controlling, preventing or protecting the animal against infestation or infection by parasites comprising, administering orally, topically or parenterally, or applying to said animal a parasiticidally effective amount of one or more compounds of claim 1.