Premium
Synthesis and Fungicidal Activity of ( E )‐Methyl 2‐(2‐((1‐cyano‐2‐hydrocarbylidenehydrazinyl)methyl)phenyl)‐2‐(methoxyimino)acetates
Author(s) -
Jia Changqing,
Yuan Xiaoyong,
Liu Xuelian,
Zhang Li,
Xiao Yumei,
Fu Bin,
Li JiaQi,
Qin Zhaohai
Publication year - 2019
Publication title -
pest management science
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.296
H-Index - 125
eISSN - 1526-4998
pISSN - 1526-498X
DOI - 10.1002/ps.5432
Subject(s) - fungicide , strobilurin , azoxystrobin , sclerotinia sclerotiorum , powdery mildew , spore germination , ec50 , chemistry , carbendazim , magnaporthe grisea , allium fistulosum , biology , horticulture , germination , in vitro , biochemistry , oryza sativa , gene , allium
BACKGROUND Strobilurin fungicides are some of the most potent and successful agrochemicals. However, continued use of traditional strobilurins has led to the emergence of fungicide‐resistant biotypes. Thus, a supply of new strobilurin fungicides is highly valuable. In this study, a series of novel methoxyacrylate analogs containing a cyano‐substituted hydrazine moiety as the side chain was synthesized and evaluated for their anti‐plant pathogenic activities. RESULTS Compounds 2‐04 , 2‐05 , 2‐07 and 2‐14 exhibited a relatively broad range of fungicidal activity. Compounds 2‐04 , 2‐13 and 2‐14 exhibited good fungicidal activity against Sclerotinia sclerotiorum with median effective concentrations (EC 50 ) of 3.84, 3.50 and 3.80 μg mL −1 , respectively. Most of these compounds showed excellent inhibition of spore germination in Magnaporthe grisea at 25 μg mL −1 . Moreover, in an in vivo test, compounds 2‐02 , 2‐04 , 2‐07 and 2‐13 exhibited potent fungicidal activities against the tested plant diseases at 400 μg mL −1 . Notably, compound 2‐07 showed comparable or better activity than the commercially positive controls, azoxystrobin and procloraz, against powdery mildew of cucumber and rice blast fungus in the field trails at the same application dosages. CONCLUSON This study indicated that methoxyacrylate analogs containing a cyano‐substituted hydrazone side chain can serve as potential fungicidal candidates for crop protection. © 2019 Society of Chemical Industry