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A Process For Preparation Of Azoxystrobin

Abstract: A process for preparation of azoxystrobin is provided. The process includes two different routes for preparing the azoxystrobin using catalyst selected from a group consisting of 4-methylmorpholine, 1,4-dimethylpiperazine, 2,2,6,6-tetramethylpiperidine, 1-methylpiperidine, and 2,2'-oxybis (N, N- dimethylethan-1-amine). The catalysts used in the process are cost-effective and have low boiling point, thus are easily recyclable. The process provided by the present invention provides higher yields and purity of the azoxystrobin than the conventional methods.

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Patent Information

Application #
Filing Date
02 March 2024
Publication Number
12/2024
Publication Type
INA
Invention Field
CHEMICAL
Status
Email
Parent Application

Applicants

NACL INDUSTRIES LIMITED
Plot No 12-A, C Block, Lakshmi Towers, Nagarjuna Hills, Punjagutta, Hyderabad 500082

Inventors

1. BHOOPAL, Meka
Flat No 304, Block-A, Vertex Pleasant, Brindavan Colony, Nizampet Road, Hyderabad 500072
2. VENKATREDDY, S.
Flat no 402, Meenkshi developers, beside Shardha Laxminarasimha Swamy Temple, New Gayatri Nagar, Jillalguda, Hyderabad 500097
3. SATYANARAYANA GOUD, Tirupathi
Bhogaram, Street-Kosgi, City-Mahabubnagar, State -Telangana, India Mahabubnagar 509339
4. CHANDRA SEKHAR, Ande
H No 5-2, PRAGADA KOTAIAH NAGAR, TENALI-522201, GUNTUR (dist), ANDHRA PRADESH, INDIA TENALI 522201
5. RAJA, Malisetti
H No 1-18, PAKALAGUDEM - 507303, SATTUPALLY (Mandal), KHAMMAM (Dist), TELANGANA, INDIA PAKALAGUDEM 507303
6. SHASHIDHAR KUMAR, Akubathini
FLAT 401, SREESAINIVAS APT, STREET NO 6, KARTHIKEYA NAGAR, NACHARAM - 500076, UPPAL (MANDAL), MEDCHAL-MALKAJGIRI (Dist), HYDERABAD, TELANGANA, INDIA HYDERABAD 500076
7. SINGH, Sunil Kumar
NACL Industries Ltd., Plot No 12-A, C Block, Lakshmi Towers, Nagarjuna Hills, Punjagutta, Hyderabad - 500082, TELANGANA, INDIA HYDERABAD 500082

Specification

We Claim:
1. A process for the preparation of Azoxystrobin of formula-1, comprising:
(a) reacting (E)-3-(methoxy methylene) benzofuran-2(3H)-one of formula-2 with sodium methoxide
and 4,6-dichloropyrimidine in presence of a catalyst to obtain the mixture of azoxystrobin
intermediates of formula-4, and formula-5;
(b) reacting the mixture of azoxystrobin intermediates of formula-4, and formula-5 with
methanesulfonic acid or p-toluenesulfonic acid to obtain methyl (E)-2-{2-[6-chloropyrimidin-4-
yloxy]phenyl}-3-methoxyacrylate of formula-5; and
(c) coupling of 2-cyanophenol with methyl (E)-2-{2-[6-chloropyrimidin-4-yloxy]phenyl}-3-
methoxyacrylate of formula-5 to obtain the azoxystrobin of formula-1.

2. The process as claimed in claim 1, the catalyst used in stage (a) is selected from a group consisting
of 4-methylmorpholine, 1,4-dimethylpiperazine, 2,2,6,6-tetramethylpiperidine, 1-
methylpiperidine, and 2,2'-oxybis (N, N-dimethylethan-1-amine) and the reaction medium used
in stage (a) includes inorganic base selected from potassium carbonate or sodium carbonate and
the solvent used in stage (a) selected from toluene or ethylene dichloride.
3. The process as claimed in claim 1, the mixture of the azoxystrobin intermediates comprise methyl
2-[2-(6-chloropyrimidin-4-yloxy) phenyl]-3,3-dimethoxypropionate of formula-4 and methyl
(E)-2-{2-[6-chloropyrimidin-4-yloxy] phenyl}-3-methoxyacrylate of formula-5.

4. The process as claimed in claim 1, reaction medium used in stage (b) includes acetic anhydride
or propionic anhydride and the solvent used in stage (b) selected from toluene or ethylene
dichloride.
5. The process as claimed in claim 1, stage (c) is carried out in presence of the catalyst bis[2-(N,Ndimethylamino)ethyl] ether and the reaction medium used in stage (c) includes potassium
carbonate and dimethyl formamide.
6. A process for the preparation of Azoxystrobin of formula-1, comprising:
(a) reacting (E)-3-(methoxy methylene) benzofuran-2(3H)-one of formula-2 with sodium methoxide
and 4,6-dichloropyrimidine in presence of a catalyst to obtain the mixture of azoxystrobin
intermediates of formula-4, and formula-5;
(b) coupling of 2-cyanophenol with the mixture of azoxystrobin intermediates of formula-4, and
formula-5 to obtain the mixture of variants of azoxystrobin of formula-7, and formula-1; and
(c) reacting the mixture of variants of azoxystrobin of formula-7, and formula-1 with
methanesulfonic acid or p-toluenesulfonic acid to isolate the pure azoxystrobin of formula-1.

7. The process as claimed in claim 6, the catalyst used in stage (a) is selected from a group consisting
of 4-methylmorpholine, 1,4-dimethylpiperazine, 2,2,6,6-tetramethylpiperidine, 1-
methylpiperidine, and 2,2'-oxybis (N, N-dimethylethan-1-amine) and the reaction medium used
in stage (a) includes an inorganic base selected from potassium carbonate or sodium carbonate
and the solvent used in stage (a) selected from toluene or ethylene dichloride.

8. The process as claimed in claim 6, the mixture of azoxystrobin intermediates comprise methyl 2-
[2-(6-chloropyrimidin-4-yloxy) phenyl]-3,3-dimethoxypropionate of formula-4 and methyl (E)-
2-{2-[6-chloropyrimidin-4-yloxy] phenyl}-3-methoxyacrylate formula-5.
9. The process as claimed in claim 6, the catalyst used in stage (b) is bis[2-(N,Ndimethylamino)ethyl] ether and the reaction medium used in stage (b) includes potassium
carbonate and dimethyl formamide.
10. The process as claimed in claim 6, the reaction medium used in stage (c) includes acetic anhydride
or propionic anhydride and the solvent used in stage (c) selected from toluene or ethylene
dichloride.

Documents

Application Documents

# Name Date
1 202447015552-STATEMENT OF UNDERTAKING (FORM 3) [02-03-2024(online)].pdf 2024-03-02
2 202447015552-REQUEST FOR EXAMINATION (FORM-18) [02-03-2024(online)].pdf 2024-03-02
3 202447015552-FORM 1 [02-03-2024(online)].pdf 2024-03-02
4 202447015552-FIGURE OF ABSTRACT [02-03-2024(online)].pdf 2024-03-02
5 202447015552-DRAWINGS [02-03-2024(online)].pdf 2024-03-02
6 202447015552-DECLARATION OF INVENTORSHIP (FORM 5) [02-03-2024(online)].pdf 2024-03-02
7 202447015552-COMPLETE SPECIFICATION [02-03-2024(online)].pdf 2024-03-02