Synthesis and herbicidal activity of novel pyrazole aromatic ketone analogs as HPPD inhibitor

Abstract

BACKGROUND 4‐Hydroxyphenylpyruvate dioxygenase (HPPD, EC 1.13.11.27) has been a good target for herbicide discovery. In order to discover novel HPPD herbicides, a series of pyrazole aromatic ketone analogs were designed and synthesized. RESULTS The 25 pyrazole aromatic ketone analogs synthesized were tested for herbicidal activity and compounds A1, A3, A4, A17, A20 and A25 displayed excellent herbicidal activity against Chenopodium serotinum, Stellaria media and Brassica juncea at 37.5 g ha−1. In addition, compounds A1, A5, A9, A10, A16, A17, A20 and A25 exhibited good crop selectivity for wheat, maize and rice at 150 g ha−1. Inhibition activities against AtHPPD proved the compounds were HPPD inhibitors. The structure–activity relationship of these pyrazole aromatic ketone analogs was studied using molecular docking. CONCLUSION These pyrazole aromatic ketone derivatives could be used as lead structures for development of HPPD herbicides against dicotyledonous weeds with further structure modification. © 2019 Society of Chemical Industry

Discovery of novel arylthioacetic acid derivatives as 4‐hydroxyphenylpyruvate dioxygenase inhibitors

“…Soybean, canola, cotton, corn, rice, and wheat were selected and underwent crop safety testing 26–29 . The commercial herbicide mesotrione was selected as a positive control.…”

“…Soybean, canola, cotton, corn, rice, and wheat were selected and underwent crop safety testing. [26][27][28][29] The commercial herbicide mesotrione was selected as a positive control. Of the tested crops, proximately 20 seeds (bud rate ≥ 85%) were sown in composite nutrient soil at a depth of 2 cm and grown at a temperature of 15 to 30°C in a glasshouse.…”

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Synthesis and Biological Activity of Benzamides Substituted with Pyridine-Linked 1,2,4-Oxadiazole

“…Many new kinds of pesticides with high efficiency, low toxicity and low residue have been developed. Heterocyclic derivatives received important attention due to their various biological activities [ 1 , 2 , 3 , 4 , 5 , 6 ]. Among these compounds, 1,2,4-oxadiazole heterocyclic derivatives, which contain nitrogen and oxygen atoms, displayed diverse activities, such as insecticidal activity [ 7 , 8 , 9 ], antifungal activity [ 10 , 11 ], herbicidal activity [ 12 ], anti-inflammatory [ 13 ], hypotensive [ 14 ] and other physiological activity.…”

Design, synthesis and antifungal activity of threoninamide carbamate derivatives via pharmacophore model

“…In recent reference, her group 17 built a modelling of the P. capsici cellulose synthase 3. In our previous work [18][19][20][21][22][23][24][25][26][27][28][29][30][31][32][33][34][35] , many bioactive compounds were designed and synthesised. In this paper, based on the structure of seven commercialised CAA fungicides, we found that they have similar structural fragments: amide bond, para-substituted phenyl, 3,4-dialkyloxy substituted phenyl.…”