The inhibitors of 4-hydroxyphenylpyruvate dioxygenase (HPPD, EC 1.13.11.27) are an new kind of herbicides.[1]Generally, in structure, potent herbicides of this kind must possess: (1) a tricarbonyl methane structure and one of the three carbonyl groups must be a subustituted benzoyl group; (2) the compound must be able to enolise so that the enolate is capable of inhibiting HPPD enzyme by competitive combination with Fe2+, the reaction center of HPPD enzyme.[2]Recently, we noticed that the 3-acyltetramic acids form an expanding group of antibiotics and pigments from micro-organisms,[3] they display a range of biological activities[4] and all of this kind compounds possess all of the characters mentioned above. Tests of their antimicrobial activities indicated that the structure of the acyl substituent at the 3-position was important to many typical antibiotics.[4～6] These characters stimulated us to study this kind of compounds so as to discover new herbicides. In this report, we synthesized a series of compounds 3 and tested their herbicidal activities to investigate their structure-activity relationships.……
A series of novel 5-sulfoxide-substituted pyrazolo[5,1-d][1,2,3,5]tetrazin-4(3H)ones 4a-j were designed and efficiently synthesized via a diazotization of 5-amine-3-methylsulfinyl- 1H-pyrazole, followed by cycloaddition with aryl isocyanate. A possible reaction mechanism is outlined and discussed. These new compounds exhibit some biological activity as preliminary bioassay indicated. Their structures were confirmed with 1H NMR, IR and elemental analysis.
Yah Chao WUXiao Mao ZOUFang Zhong HUHua Zheng YANG
