Pyraquinate is a herbicide containing the quinazolinone compound and provides a novel HPPD-based inhibitor which has excellent control effects on weeds in crop fields such as paddy fields and high safety against crops. Pyraquinate is discovered and developed by Chinese Player Shandong Cynda Chemical.
MOLECULE DETAILS:
- STATUS: ISO 1750 (provisionally approved)
- IUPAC NAME: 4-{[3-(3-chlorophenyl)-1,5-dimethyl-2,4-dioxo-1,2,3,4-tetrahydroquinazolin-6-yl]carbonyl}-1,3-dimethyl-1H-pyrazol-5-yl diethylcarbamate
- CAS RN.: 2378093-62-8
- ACTIVITY: Herbicides
- CHEMICAL CLASS: Benzoylpyrazole
PATENT INFORMATION:
Shandong Cynda Chemical filed international patent application covering the active ingredient Pyraquinate
- WO2019196904 is a compound patent of Pyraquinate filed by Shandong Cynda Chemical on 2019-04-11 and it was published on 2019-10-17.
- CN111820231A is a combination patent of Pyraquinate filed by Shandong Cynda Chemical on 2020-04-16 and it was published on 2020-10-27.
Pyraquinate and its analog herbicidal activities disclosed in the patent:
The above herbicidal activity test results showed that compound 1 and compound 2 of the present invention have excellent control effects against weeds. Moreover, the compound of the present invention is superior to the commercial agent mesotrione in the control effect of foxtail.
Comparing Compound D1 – Compound D11, Compound D1 – Compound D11 has a lower control effect on test weeds than the compound of the present invention, and the difference in the control effect of each compound on different weeds is more obvious. In particular, compound D8 and compound D11 have substantially no control effect on the test weeds.
Further, when the pyrazole ring fragment in the structure of the compound of the present invention is subjected to modification of a substituent, and the methyl group, the ethyl group, the propyl group, and the cyclopropyl group are introduced, the herbicidal activity of the synthesized compound D12 to the compound D15 is remarkably superior. The corresponding drug compound D36 to compound D39. This explains from the side that the N,N-diethylformyl fragment specifically found by the inventors of the present invention has a significant promoting effect on enhancing the herbicidal activity of HPPD-based inhibitors.
In order to further verify the promoting effect of N,N-diethylformyl fragment on biological activity, the N,N-diethylformyl fragment was cyclized, and it was widely used in pesticides and medicines and had good biological activity. The five- or six-membered ring synthesizes compound D16 to compound D19, however, the herbicidal activity of this series of compounds is substantially lost. On the basis of this, the formyl group is retained to introduce other substituted alkyl groups such as an alkoxy group, a three-membered ring, a four-membered ring, a five-membered ring, and a six-membered ring. In the general screening experiment, the herbicidal activity of the derivatives of the furan ring and the thiophene ring is optimal and is similar to the herbicidal activity of the compound of the present invention.
By comparative analysis, when a three-membered ring or a four-membered ring is introduced (compound D21, compound D22, compound D23, compound D24), the herbicidal activity is generally reduced, and when other substituted alkyl groups such as alkoxy groups are introduced, the herbicidal activity is relative to The prodrug molecule is improved, and the control effect on grass weeds is comparable to that of the compound of the present invention, but the control effect on broadleaf weeds is worse than that of the compound of the present invention.
As a comprehensive analysis, the N,N-diethylformyl fragment has an important effect on increasing the herbicidal activity of the HPPD-based inhibitor of the present invention.
About Shandong Cynda Chemical Co., Ltd.,
Shandong Cynda Chemical Co., Ltd., is one of the leading agrochemical companies in China founded by Mr. Wang Xianquan in 1998. They owned three production bases (Boxing Cynda, Weifang Cynda, and Liaoning Cyand) and one sales window (Jinan Cynda).
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