4-Hydroxyphenylpyruvate dioxygenase (EC 1.13.11.27, HPPD) belongs to the non-heme Fe2+ -containing enzyme family and is an important enzyme in tyrosine decomposition. HPPD is crucial to the discovery of novel bleaching herbicides. To develop novel HPPD inhibitor herbicides containing the & beta;-triketone motif, a series of 4-hydroxyl-3-(substituted aryl)-pyran-2-one derivatives were designed using the active fragment splicing method. The title compounds were synthesized and characterized through infrared spectroscopy (IR), 1H nuclear mag-netic resonance (1H NMR), 13C nuclear magnetic resonance (13C NMR), and high-resolution mass spectrometry (HRMS). The X-ray diffraction method determined the single crystal structure of I-17. Preliminary bioassay data revealed that several novel compounds, especially I-12 and II-3, showed excellent herbicidal activity against broadleaf and monocotyledonous weeds at a dose of 150 g ai/ha. The results of crop selectivity and carotenoids determination indicated that compound I-12 is more suitable for wheat and cotton fields than mesotrione. Additionally, compound II-3 is safer for soybeans and peanuts than mesotrione. The inhibitory activity of Ara-bidopsis thaliana HPPD (AtHPPD) verified that compound II-3 showed the most activity with an IC50 value of 0.248 & mu;M, which was superior to that of mesotrione (0.283 & mu;M) in vitro. The binding mode of compound II-3 and AtHPPD was confirmed through molecular docking and molecular dynamics simulations. This study provides insights into the future development of natural and efficient herbicides.
机构:
Peking Union Med Coll, State Key Lab Bioact Subst & Funct Nat Med, Beijing 100050, Peoples R China
Peking Union Med Coll, Beijing Key Lab Act Subst Discovery & Druggabil E, Inst Mat Med, Beijing 100050, Peoples R China
Chinese Acad Med Sci, Beijing 100050, Peoples R ChinaPeking Union Med Coll, State Key Lab Bioact Subst & Funct Nat Med, Beijing 100050, Peoples R China
Zhang, Feng
Han, Bei
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Peking Union Med Coll, State Key Lab Bioact Subst & Funct Nat Med, Beijing 100050, Peoples R China
Peking Union Med Coll, Beijing Key Lab Act Subst Discovery & Druggabil E, Inst Mat Med, Beijing 100050, Peoples R China
Chinese Acad Med Sci, Beijing 100050, Peoples R ChinaPeking Union Med Coll, State Key Lab Bioact Subst & Funct Nat Med, Beijing 100050, Peoples R China
Han, Bei
Li, Peng
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Peking Union Med Coll, State Key Lab Bioact Subst & Funct Nat Med, Beijing 100050, Peoples R China
Peking Union Med Coll, Beijing Key Lab Act Subst Discovery & Druggabil E, Inst Mat Med, Beijing 100050, Peoples R China
Chinese Acad Med Sci, Beijing 100050, Peoples R ChinaPeking Union Med Coll, State Key Lab Bioact Subst & Funct Nat Med, Beijing 100050, Peoples R China
Li, Peng
Lin, Ziyun
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Peking Union Med Coll, State Key Lab Bioact Subst & Funct Nat Med, Beijing 100050, Peoples R China
Peking Union Med Coll, Beijing Key Lab Act Subst Discovery & Druggabil E, Inst Mat Med, Beijing 100050, Peoples R China
Chinese Acad Med Sci, Beijing 100050, Peoples R ChinaPeking Union Med Coll, State Key Lab Bioact Subst & Funct Nat Med, Beijing 100050, Peoples R China
Lin, Ziyun
Yin, Dali
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Peking Union Med Coll, State Key Lab Bioact Subst & Funct Nat Med, Beijing 100050, Peoples R China
Peking Union Med Coll, Beijing Key Lab Act Subst Discovery & Druggabil E, Inst Mat Med, Beijing 100050, Peoples R China
Chinese Acad Med Sci, Beijing 100050, Peoples R ChinaPeking Union Med Coll, State Key Lab Bioact Subst & Funct Nat Med, Beijing 100050, Peoples R China
Yin, Dali
Li, Yan
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Peking Union Med Coll, State Key Lab Bioact Subst & Funct Nat Med, Beijing 100050, Peoples R China
Peking Union Med Coll, Beijing Key Lab Act Subst Discovery & Druggabil E, Inst Mat Med, Beijing 100050, Peoples R China
Chinese Acad Med Sci, Beijing 100050, Peoples R ChinaPeking Union Med Coll, State Key Lab Bioact Subst & Funct Nat Med, Beijing 100050, Peoples R China
Li, Yan
Zhong, Jialiang
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Shanghai Inst Pharmaceut Ind, Shanghai 200040, Peoples R ChinaPeking Union Med Coll, State Key Lab Bioact Subst & Funct Nat Med, Beijing 100050, Peoples R China
Zhong, Jialiang
Huang, Haihong
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Peking Union Med Coll, State Key Lab Bioact Subst & Funct Nat Med, Beijing 100050, Peoples R China
Peking Union Med Coll, Beijing Key Lab Act Subst Discovery & Druggabil E, Inst Mat Med, Beijing 100050, Peoples R China
Chinese Acad Med Sci, Beijing 100050, Peoples R ChinaPeking Union Med Coll, State Key Lab Bioact Subst & Funct Nat Med, Beijing 100050, Peoples R China
机构:
Guizhou Univ, State Key Lab Green Pesticide, Key Lab Green Pesticide & Agr Bioengn, Minist Educ, Guiyang 550025, Peoples R ChinaGuizhou Univ, State Key Lab Green Pesticide, Key Lab Green Pesticide & Agr Bioengn, Minist Educ, Guiyang 550025, Peoples R China
Ou, Yuqin
Guo, Xue
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Guizhou Univ, State Key Lab Green Pesticide, Key Lab Green Pesticide & Agr Bioengn, Minist Educ, Guiyang 550025, Peoples R ChinaGuizhou Univ, State Key Lab Green Pesticide, Key Lab Green Pesticide & Agr Bioengn, Minist Educ, Guiyang 550025, Peoples R China
Guo, Xue
Zhang, Qi
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Guizhou Univ, State Key Lab Green Pesticide, Key Lab Green Pesticide & Agr Bioengn, Minist Educ, Guiyang 550025, Peoples R ChinaGuizhou Univ, State Key Lab Green Pesticide, Key Lab Green Pesticide & Agr Bioengn, Minist Educ, Guiyang 550025, Peoples R China
Zhang, Qi
Zhang, Wei
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Guizhou Univ, State Key Lab Green Pesticide, Key Lab Green Pesticide & Agr Bioengn, Minist Educ, Guiyang 550025, Peoples R ChinaGuizhou Univ, State Key Lab Green Pesticide, Key Lab Green Pesticide & Agr Bioengn, Minist Educ, Guiyang 550025, Peoples R China
Zhang, Wei
Gan, Xiuhai
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Guizhou Univ, State Key Lab Green Pesticide, Key Lab Green Pesticide & Agr Bioengn, Minist Educ, Guiyang 550025, Peoples R ChinaGuizhou Univ, State Key Lab Green Pesticide, Key Lab Green Pesticide & Agr Bioengn, Minist Educ, Guiyang 550025, Peoples R China
机构:
Yale Univ, Sch Med, New Haven, CT 06510 USA
Albert Einstein Coll Med, Dept Dev & Mol Biol, Bronx, NY 10461 USAYale Univ, Sch Med, New Haven, CT 06510 USA
Jubinsky, Paul T.
Short, Mary K.
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Albert Einstein Coll Med, Dept Dev & Mol Biol, Bronx, NY 10461 USAYale Univ, Sch Med, New Haven, CT 06510 USA
Short, Mary K.
Ghanem, Mohmoud
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Albert Einstein Coll Med, Dept Biochem, Bronx, NY 10461 USAYale Univ, Sch Med, New Haven, CT 06510 USA
Ghanem, Mohmoud
Das, Bhaskar C.
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Albert Einstein Coll Med, Dept Dev & Mol Biol, Bronx, NY 10461 USA
Albert Einstein Coll Med, Dept Nucl Med, Bronx, NY 10461 USAYale Univ, Sch Med, New Haven, CT 06510 USA
机构:
Guizhou Univ, Res & Dev Ctr Fine Chem, State Key Lab Breeding Base Green Pesticide & Agr, Key Lab Green Pesticide & Agr Bioengn,Minist Educ, Guiyang 550025, Peoples R ChinaGuizhou Univ, Res & Dev Ctr Fine Chem, State Key Lab Breeding Base Green Pesticide & Agr, Key Lab Green Pesticide & Agr Bioengn,Minist Educ, Guiyang 550025, Peoples R China
Chen, Shuai
Zhang, Miaohe
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Guizhou Univ, Res & Dev Ctr Fine Chem, State Key Lab Breeding Base Green Pesticide & Agr, Key Lab Green Pesticide & Agr Bioengn,Minist Educ, Guiyang 550025, Peoples R ChinaGuizhou Univ, Res & Dev Ctr Fine Chem, State Key Lab Breeding Base Green Pesticide & Agr, Key Lab Green Pesticide & Agr Bioengn,Minist Educ, Guiyang 550025, Peoples R China
Zhang, Miaohe
Feng, Shuang
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Guizhou Univ, Res & Dev Ctr Fine Chem, State Key Lab Breeding Base Green Pesticide & Agr, Key Lab Green Pesticide & Agr Bioengn,Minist Educ, Guiyang 550025, Peoples R ChinaGuizhou Univ, Res & Dev Ctr Fine Chem, State Key Lab Breeding Base Green Pesticide & Agr, Key Lab Green Pesticide & Agr Bioengn,Minist Educ, Guiyang 550025, Peoples R China
Feng, Shuang
Gong, Chenyu
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Guizhou Univ, Res & Dev Ctr Fine Chem, State Key Lab Breeding Base Green Pesticide & Agr, Key Lab Green Pesticide & Agr Bioengn,Minist Educ, Guiyang 550025, Peoples R ChinaGuizhou Univ, Res & Dev Ctr Fine Chem, State Key Lab Breeding Base Green Pesticide & Agr, Key Lab Green Pesticide & Agr Bioengn,Minist Educ, Guiyang 550025, Peoples R China
Gong, Chenyu
Zhou, Yuanxiang
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Guizhou Univ, Res & Dev Ctr Fine Chem, State Key Lab Breeding Base Green Pesticide & Agr, Key Lab Green Pesticide & Agr Bioengn,Minist Educ, Guiyang 550025, Peoples R ChinaGuizhou Univ, Res & Dev Ctr Fine Chem, State Key Lab Breeding Base Green Pesticide & Agr, Key Lab Green Pesticide & Agr Bioengn,Minist Educ, Guiyang 550025, Peoples R China
Zhou, Yuanxiang
Xing, Li
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Guizhou Univ, Res & Dev Ctr Fine Chem, State Key Lab Breeding Base Green Pesticide & Agr, Key Lab Green Pesticide & Agr Bioengn,Minist Educ, Guiyang 550025, Peoples R ChinaGuizhou Univ, Res & Dev Ctr Fine Chem, State Key Lab Breeding Base Green Pesticide & Agr, Key Lab Green Pesticide & Agr Bioengn,Minist Educ, Guiyang 550025, Peoples R China
Xing, Li
He, Bangcan
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Guizhou Univ, Res & Dev Ctr Fine Chem, State Key Lab Breeding Base Green Pesticide & Agr, Key Lab Green Pesticide & Agr Bioengn,Minist Educ, Guiyang 550025, Peoples R ChinaGuizhou Univ, Res & Dev Ctr Fine Chem, State Key Lab Breeding Base Green Pesticide & Agr, Key Lab Green Pesticide & Agr Bioengn,Minist Educ, Guiyang 550025, Peoples R China
He, Bangcan
Wu, Yongjun
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机构:
Guizhou Univ, Coll Life Sci, Key Lab Plant Resource Conservat & Germplasm Innov, Minist Educ, Guiyang 550025, Guizhou, Peoples R ChinaGuizhou Univ, Res & Dev Ctr Fine Chem, State Key Lab Breeding Base Green Pesticide & Agr, Key Lab Green Pesticide & Agr Bioengn,Minist Educ, Guiyang 550025, Peoples R China
Wu, Yongjun
Xue, Wei
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Guizhou Univ, Res & Dev Ctr Fine Chem, State Key Lab Breeding Base Green Pesticide & Agr, Key Lab Green Pesticide & Agr Bioengn,Minist Educ, Guiyang 550025, Peoples R ChinaGuizhou Univ, Res & Dev Ctr Fine Chem, State Key Lab Breeding Base Green Pesticide & Agr, Key Lab Green Pesticide & Agr Bioengn,Minist Educ, Guiyang 550025, Peoples R China
机构:
Nihon Nohyaku Co Ltd, Res Ctr, Res Div, 345 Oyamada Cho, Osaka 5860094, JapanNihon Nohyaku Co Ltd, Res Ctr, Res Div, 345 Oyamada Cho, Osaka 5860094, Japan
Satoh, Eikoh
Kasahara, Ryota
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Nihon Nohyaku Co Ltd, Res Ctr, Res Div, 345 Oyamada Cho, Osaka 5860094, JapanNihon Nohyaku Co Ltd, Res Ctr, Res Div, 345 Oyamada Cho, Osaka 5860094, Japan
Kasahara, Ryota
Fukatsu, Kosuke
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Nihon Nohyaku Co Ltd, Res Ctr, Res Div, 345 Oyamada Cho, Osaka 5860094, JapanNihon Nohyaku Co Ltd, Res Ctr, Res Div, 345 Oyamada Cho, Osaka 5860094, Japan
Fukatsu, Kosuke
Aoki, Takao
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机构:
Nihon Nohyaku Co Ltd, Res Ctr, Res Div, 345 Oyamada Cho, Osaka 5860094, JapanNihon Nohyaku Co Ltd, Res Ctr, Res Div, 345 Oyamada Cho, Osaka 5860094, Japan
Aoki, Takao
Harayama, Hiroto
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Nihon Nohyaku Co Ltd, Res Ctr, Res Div, 345 Oyamada Cho, Osaka 5860094, JapanNihon Nohyaku Co Ltd, Res Ctr, Res Div, 345 Oyamada Cho, Osaka 5860094, Japan
Harayama, Hiroto
Murata, Tetsuya
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Nihon Nohyaku Co Ltd, Res Ctr, Res Div, 345 Oyamada Cho, Osaka 5860094, JapanNihon Nohyaku Co Ltd, Res Ctr, Res Div, 345 Oyamada Cho, Osaka 5860094, Japan