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Synthesis of Novel 6-Aryloxy-4-chloro-2-phenylpyrimidines as Fungicides and Herbicide Safeners
ACS Omega ( IF 3.7 ) Pub Date : 2020-09-10 , DOI: 10.1021/acsomega.0c03300 Xile Deng 1 , Wenna Zheng 1 , Can Jin 1 , Lianyang Bai 1
ACS Omega ( IF 3.7 ) Pub Date : 2020-09-10 , DOI: 10.1021/acsomega.0c03300 Xile Deng 1 , Wenna Zheng 1 , Can Jin 1 , Lianyang Bai 1
Affiliation
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Fenclorim is a commercial herbicide safener with fungicidal activity used for chloroacetanilide herbicides, which might be suitable as a lead compound for screening novel fungicides. However, little has been reported so far on the structure–activity relationship of fungicidal activities of fenclorim or its analogues. Here, a series of 4-chloro-6-substituted phenoxy-2-phenylpyrimidine derivatives was synthesized by a substructure splicing route using fenclorim as a lead compound. The structures of synthesized derivatives were characterized by 1H NMR, 13C NMR, and HRMS. Their fungicidal and herbicide safening activities were then evaluated. The results revealed that compound 11 had the best fungicidal activity against Sclerotinia sclerotiorum and Thanatephorus cucumeris, which was better than that of the control pyrimethanil. Moreover, compounds 3, 5, and 25 exhibited excellent safening activities against fresh weight, plant height, and root length, respectively. Such activities were significantly improved when compared to fenclorim. In summary, these findings look promising for the preparation of new fungicides and herbicide safeners based on the structure of fenclorim.
中文翻译：
新型6-芳氧基-4-氯-2-苯基嘧啶类化合物的合成及杀菌作用
Fenclorim是一种具有杀真菌活性的商品化除草剂安全剂，用于氯乙酰苯胺除草剂，可能适合作为筛选新型杀真菌剂的先导化合物。然而，到目前为止，关于芬克洛林或其类似物的杀真菌活性的结构-活性关系的报道很少。在此，通过以芬克洛林为先导化合物的亚结构剪接途径合成了一系列4-氯-6-取代的苯氧基-2-苯基嘧啶衍生物。合成衍生物的结构通过1 H NMR，13 C NMR和HRMS进行表征。然后评估了它们的杀真菌和除草剂安全性。结果表明，化合物11对菌核菌的杀菌活性最好。和黄瓜甜瓜（Thanatephorus cucumeris），比对照嘧啶醇更好。此外，化合物3，5，和25对鲜重，株高，和根长，分别表现出优异的安全化活性。与芬克洛林相比，此类活性得到了显着改善。总而言之，这些发现对于基于芬克洛林的结构制备新的杀菌剂和除草剂安全剂看起来很有希望。
更新日期：2020-09-22
中文翻译：
新型6-芳氧基-4-氯-2-苯基嘧啶类化合物的合成及杀菌作用
Fenclorim是一种具有杀真菌活性的商品化除草剂安全剂，用于氯乙酰苯胺除草剂，可能适合作为筛选新型杀真菌剂的先导化合物。然而，到目前为止，关于芬克洛林或其类似物的杀真菌活性的结构-活性关系的报道很少。在此，通过以芬克洛林为先导化合物的亚结构剪接途径合成了一系列4-氯-6-取代的苯氧基-2-苯基嘧啶衍生物。合成衍生物的结构通过1 H NMR，13 C NMR和HRMS进行表征。然后评估了它们的杀真菌和除草剂安全性。结果表明，化合物11对菌核菌的杀菌活性最好。和黄瓜甜瓜（Thanatephorus cucumeris），比对照嘧啶醇更好。此外，化合物3，5，和25对鲜重，株高，和根长，分别表现出优异的安全化活性。与芬克洛林相比，此类活性得到了显着改善。总而言之，这些发现对于基于芬克洛林的结构制备新的杀菌剂和除草剂安全剂看起来很有希望。
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