Several different alkoxycarbonyl-substituted 2-benzoxazolinone moieties have been incorporated into a tetrahy- droisoindoline-1,3-dione scaffold to provide 25 compounds （1a-lu and 2a-2d）. The structures of these com...Several different alkoxycarbonyl-substituted 2-benzoxazolinone moieties have been incorporated into a tetrahy- droisoindoline-1,3-dione scaffold to provide 25 compounds （1a-lu and 2a-2d）. The structures of these compounds were confirmed by 1H and 13C NMR, HRMS and X-ray single-crystal diffraction. Some of these compounds （1g, 1h, 1j, 1k） exhibited excellent herbicidal activities against Abutilon theophrasti, Amaranthus retroflexus and Eehinochloa crus-galli at a rate of 375 g AI·ha^-1. Among them, compounds lh and 1j displayed the best post-emergence herbicidal effect against Abutilon theophrasti with ED50 values of 1.8 and 5.3 g AI·ha^-1, respectively, which are superior to that of the commercial acifluorfen （44.3 g AI·ha^-1）. Field trials demonstrated that compound lh exhibited similar herbicidal activity to a high concentration atrazine, and found to be safer for maize than atrazine. The results of this study therefore show that compound lh could potentially be used as a post-emergence herbicide for maize fields.展开更多
In order to find novel protoporphyrinogen oxidase inhibitors with high efficacy, broad-spectrum activity, and safety to crops, nine title compounds（4a-4i） were designed and synthesized by introducing pyrimidine moie...In order to find novel protoporphyrinogen oxidase inhibitors with high efficacy, broad-spectrum activity, and safety to crops, nine title compounds（4a-4i） were designed and synthesized by introducing pyrimidine moiety into the uracil skeleton with commercially herbicide butafenacil as the lead compound. Their structures were con- firmed by 1H NMR, IR, mass spectroscopy and elemental analysis. The bioassay results indicate that most of com- pounds 4 tested exhibit good to excellent herbicidal activities against B. campestris, A. retroflexus, E. crusgalli and D. sanguinalis in pre-emergence treatment at a dose of 1.5 kg/ha（1 ha=10^4 m^2）, for example, compound 4i showed 100% inhibition against the four plants tested in pre-emergence treatment at a dose of 1.5 kg/ha. So, this type of skeleton can be used as a valuable lead compound for the further development of a pre-emergent herbicide.展开更多
基金This work was supported by the National Key Technologies R＆D Program （No. 2011BAE06B03）, and National Natural Science Foundation of China （No. 21172256）.
文摘Several different alkoxycarbonyl-substituted 2-benzoxazolinone moieties have been incorporated into a tetrahy- droisoindoline-1,3-dione scaffold to provide 25 compounds （1a-lu and 2a-2d）. The structures of these compounds were confirmed by 1H and 13C NMR, HRMS and X-ray single-crystal diffraction. Some of these compounds （1g, 1h, 1j, 1k） exhibited excellent herbicidal activities against Abutilon theophrasti, Amaranthus retroflexus and Eehinochloa crus-galli at a rate of 375 g AI·ha^-1. Among them, compounds lh and 1j displayed the best post-emergence herbicidal effect against Abutilon theophrasti with ED50 values of 1.8 and 5.3 g AI·ha^-1, respectively, which are superior to that of the commercial acifluorfen （44.3 g AI·ha^-1）. Field trials demonstrated that compound lh exhibited similar herbicidal activity to a high concentration atrazine, and found to be safer for maize than atrazine. The results of this study therefore show that compound lh could potentially be used as a post-emergence herbicide for maize fields.
基金Supported by the National Natural Science Foundation of China（No.21342004） and the Open Project of Key Laboratory of Theoretical Chemistry and Molecular Simulation of Ministry of Education, Hunan University of Science and Technology, China（No.LKF 1206）.
文摘In order to find novel protoporphyrinogen oxidase inhibitors with high efficacy, broad-spectrum activity, and safety to crops, nine title compounds（4a-4i） were designed and synthesized by introducing pyrimidine moiety into the uracil skeleton with commercially herbicide butafenacil as the lead compound. Their structures were con- firmed by 1H NMR, IR, mass spectroscopy and elemental analysis. The bioassay results indicate that most of com- pounds 4 tested exhibit good to excellent herbicidal activities against B. campestris, A. retroflexus, E. crusgalli and D. sanguinalis in pre-emergence treatment at a dose of 1.5 kg/ha（1 ha=10^4 m^2）, for example, compound 4i showed 100% inhibition against the four plants tested in pre-emergence treatment at a dose of 1.5 kg/ha. So, this type of skeleton can be used as a valuable lead compound for the further development of a pre-emergent herbicide.
