SSF-126: a novel antifungal alkoxyiminoacetamide derivative for control of rice blast
1994
Masuko, M. | Niikawa, N. | Kataoka, T. | Ichinari, M. | Takenaka, T. | Hayase, Y. | Hayashi, Y. | Takeda, R. (Aburahi Lab., Shionogi and Co. Ltd., Shiga, 520-34 (Japan))
New alkoxyiminoacetamide derivatives were synthesized and their biological characteristics as a new class of fungicide were assessed. From the structure-activity relationship, it was demonstrated that when oxyimino moiety is methyl ether (R1 = Me), and acetamide moiety is mono-methyl amine (either R2 or R3 is H and the rest is Me), the fungicidal activity was the best. The phenoxy group should be attached to the ortho-position of the phenyl ring, and the other substituents on the phenyl ring (R4) of phenylacetamide moiety besides the ortho-phenoxy group reduced the fungicidal activity. Between two geometrical isomers, the (E)-form was stronger than the (Z)-form. Consequently, (E)-2-methixyimino-N-methyl-1-(2-phenoxyphenyl) acetamide (SSF-126) exhibited excellent fungicidal activity. Although SSF-126 is active against a wide range of diseases, it shows excellent activity against rice blast by leaf spray as well as submerged application into paddy water. On the other hand, the compound showed weak fungicidal activity in vitro. It did not inhibit spore germination or mycelial growth of Pyricularia oryzae at less than 200 ppm. In pot tests, SSF-126 showed good preventive and curative properties by foliar application; however, the controlling activity of SSF-126 against rice blast was excellent when it was applied into the paddy water. SSF-126 also exhibited good control against rice sheath blight and Helminthosporium leaf spot as well. Under field conditions, SSF-126 showed excellent control against ear blast as well as leaf blast by one-shot application into the paddy water by granular formulation just before or even after the outbreak of symptom on the leaf at the dose rate of 1800 g a.i./ha
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