Pest management science · 2025
Design and synthesis of strigolactone analogues and mimics containing indolin-2-one scaffold for the Phelipanche control.
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Lu Qianghui, Mo Meilin, Liang Yinhao, Xu Niuniu, Chen Lianfang, Xu Xiaohua, Jin Zhong
Аннотация
BACKGROUND: The broomrapes are root-parasitic weeds widely distributed in the temperate zone area. The effective management on the Phelipanche and Orobanche parasitic weeds still remains challenging to date.
RESULTS: Novel strigolactone (SL) analogues (X series) and mimics (O series) derived from indolin-2-one were designed and synthesized. Of them, compound O-3 showed nearly ten-fold higher seed germination activity (median effective concentration (EC50) = 0.0066 μm) towards Phelipanche aegyptiaca seeds compared to the control GR24. Moreover, it also showed prominent seed germination activity towards Phelipanche ramosa. At a dosage of 0.2 μm, the glasshouse experiment revealed that compound O-3 not only displayed the profitable P. aegyptiaca control, but also influenced fruit and plant stalk development in tomato cultivation. Theoretical computational studies indicated that compound O-3 could perfectly interact with catalytic triad of OmKAI2d4, and the oxime linker facilitate to release the active D ring species, thereby significantly improving bioactivity.
CONCLUSIONS: A class of SL mimics incorporating a unique oxime linker has been developed from indolin-2-one. Compound O-3 exhibited the highest seed germination activities toward the parasitic P. aegyptiaca and P. ramosa, and could serve as a promising lead compound for the Phelipanche control. © 2025 Society of Chemical Industry.
RESULTS: Novel strigolactone (SL) analogues (X series) and mimics (O series) derived from indolin-2-one were designed and synthesized. Of them, compound O-3 showed nearly ten-fold higher seed germination activity (median effective concentration (EC50) = 0.0066 μm) towards Phelipanche aegyptiaca seeds compared to the control GR24. Moreover, it also showed prominent seed germination activity towards Phelipanche ramosa. At a dosage of 0.2 μm, the glasshouse experiment revealed that compound O-3 not only displayed the profitable P. aegyptiaca control, but also influenced fruit and plant stalk development in tomato cultivation. Theoretical computational studies indicated that compound O-3 could perfectly interact with catalytic triad of OmKAI2d4, and the oxime linker facilitate to release the active D ring species, thereby significantly improving bioactivity.
CONCLUSIONS: A class of SL mimics incorporating a unique oxime linker has been developed from indolin-2-one. Compound O-3 exhibited the highest seed germination activities toward the parasitic P. aegyptiaca and P. ramosa, and could serve as a promising lead compound for the Phelipanche control. © 2025 Society of Chemical Industry.