# US 2019/0315728 A1 · Process for the preparation of thietane derivatives

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

- Number: US 2019/0315728 A1
- Document ID: US20190315728A1
- Status: Published application
- Kind: A1
- Application number: 16/389,116
- Filed: 2019-04-19
- Published: 2019-10-17
- Earliest claimed: 2011-08-25
- Assignees: Syngenta Participations AG
- Applicants: Syngenta Participations AG
- Inventors: Jerome Yves CASSAYRE; Peter RENOLD; Thomas PITTERNA; Myriem EL QACEMI
- Web page: https://patentgrep.com/patent/US20190315728A1

## CPC

- C07D 413/12: linked by a chain containing hetero atoms as chain links
- A01N 43/36: five-membered rings
- A01N 43/80: five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2
- A61P 33/00: Antiparasitic agents
- A61P 33/14: Ectoparasiticides, e.g. scabicides
- C07D 331/04: Four-membered rings
- C07D 409/12: linked by a chain containing hetero atoms as chain links
- 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 processes for the preparation of thietane derivatives of the formula IA and thietane derivatives of the formula IB wherein R1, R2, A1, A2, A3, A4, B, and n are as defined in the claims. The invention also relates to intermediates useful in the processes, as well as the compounds of formula IA and IB and their use as pesticides.

## Claims

### Claim 1

(canceled)

### Claim 2

A process for preparing a compound of formula X
comprising
i. reacting a compound of formula VII
with triphenylphosphoranyldiene-acetonitrile or (Cyanomethyl)diethoxyphosphine oxide to give a compound of formula VIII
ii. reducing the compound of formula VIII with a suitable reducing agent to give a compound of formula X.

### Claim 3

A compound of formula IB
wherein
A1, A2, A3 and A4 are independently of one another C—H, C—R3, or nitrogen;
B is O or CH2;
R1 is C1-C8haloalkyl;
R2 is aryl or aryl substituted by one to five R4, or heteroaryl or heteroaryl substituted by one to five R4;
each R3 is independently halogen, cyano, nitro, C1-C8alkyl, C3-C8cycloalkyl, C1-C8haloalkyl, C2-C8alkenyl, C2-C8haloalkenyl, C2-C8alkynyl, C2-C8haloalkynyl, C1-C8alkoxy, C1-C8haloalkoxy, C1-C8alkoxycarbonyl-, amino, hydroxy, mercapto, C1-C8alkylthio, C1-C8haloalkylthio, C1-C8alkylsulfinyl, C1-C8haloalkylsulfinyl, C1-C8alkylsulfonyl, C1-C8haloalkylsulfonyl, C1-C8alkylcarbonyl, or two R3 on adjacent carbon atoms together form a —CH═CH—CH═CH— bridge or a —N═CH—CH═CH— bridge;
each R4 is independently halogen, cyano, nitro, C1-C8alkyl, C1-C8haloalkyl, C2-C8alkenyl, C2-C8haloalkenyl, C2-C8alkynyl, C2-C8haloalkynyl, hydroxy, C1-C8alkoxy, C1-C8haloalkoxy, mercapto, C1-C8alkylthio, C1-C8haloalkylthio, C1-C8alkylsulfinyl, C1-C8haloalkylsulfinyl, C1-C8alkylsulfonyl, C1-C8haloalkylsulfonyl, C1-C8alkylcarbonyl, C1-C8alkoxycarbonyl, aryl or aryl substituted by one to five R5, or heterocyclyl or heterocyclyl substituted by one to five R5;
each R5 is independently halogen, cyano, nitro, C1-C4alkyl, C1-C4haloalkyl, C1-C4alkoxy-, or C1-C4haloalkoxy-;
n is 0, 1 or 2.

### Claim 4

A compound of formula VIII, X or XV
wherein n is 1 or 2, or a compound of formula XI, XII or XIII
wherein R is C1-C6alkyl.

### Claim 5

(canceled)

### Claim 6 (depends on 3)

A method of combating and controlling insects, acarines, nematodes or molluscs which comprises applying to a pest, to a locus of a pest, or to a plant susceptible to attack by a pest an insecticidally, acaricidally, nematicidally or molluscicidally effective amount of a compound of formula (IB) as defined in claim 3.

### Claim 7 (depends on 3)

An insecticidal, acaricidal, nematicidal or molluscicidal composition comprising an insecticidally, acaricidally, nematicidally or molluscicidally effective amount of a compound of formula (IB) as defined in claim 3, and optionally comprising an additional pesticidally active ingredient.

### Claim 8 (depends on 3)

A combination product comprising a pesticidally effective amount of a component A and a pesticidally effective amount of component B, wherein component A is a compound of formula (IB) as defined in claim 3, and component B is imidacloprid, enrofloxacin, praziquantel, pyrantel embonate, febantel, penethamate, moloxicam, cefalexin, kanamycin, pimobendan, clenbuterol, fipronil, ivermectin, omeprazole, tiamulin, benazepril, milbemycin, cyromazine, thiamethoxam, pyriprole, deltamethrin, cefquinome, florfenicol, buserelin, cefovecin, tulathromycin, ceftiour, selamectin, carprofen, metaflumizone, moxidectin, methoprene (including S-methoprene), clorsulon, pyrantel, amitraz, triclabendazole, avermectin, abamectin, emamectin, eprinomectin, doramectin, selamectin, nemadectin, albendazole, cambendazole, fenbendazole, flubendazole, mebendazole, oxfendazole, oxibendazole, parbendazole, tetramisole, levamisole, pyrantel pamoate, oxantel, morantel, triclabendazole, epsiprantel, fipronil, lufenuron, ecdysone or tebufenozide.

### Claim 9 (depends on 4)

The compound of claim 4, wherein the compound is the compound of formula VIII.

### Claim 10 (depends on 4)

The compound of claim 4, wherein the compound is the compound of formula X.

### Claim 11 (depends on 4)

The compound of claim 4, wherein the compound is the compound of formula XV.

### Claim 12 (depends on 4)

The compound of claim 4, wherein the compound is the compound of formula XI.

### Claim 13 (depends on 4)

The compound of claim 4, wherein the compound is the compound of formula XII.

### Claim 14 (depends on 4)

The compound of claim 4, wherein the compound is the compound of formula XIII.