Nihon Nohyaku Co. Ltd

Flutolanil is a benzanilide fungicide discovered and developed by Nihon Nohyaku Co., Ltd. Flutolanil exhibits excellent control against the following pathogens at rates of 300-1000gha (foliar spray), 1.5-3.0gkg (seed treatment) and 2.5-10.0 kg ha (soil incorporation) Rhizoctonia solani on rice. 

Yuji Ikemoto Nihon Nohyaku Co. Ltd, Osaka, Japan... 

The authors would like to express sincere thanks to all their distinguished colleagues involved in the discovery of flubendiamide in Nihon Nohyaku Co., Ltd. The authors also wish to acknowledge the many scientists at Bayer CropScience AG and Professor Yasuo Mori at Kyoto University during the course of the mode of action work. 

This ranking of halogen atoms can be exemplified by the recently described SAR of halogenated phthalic acid diamides (F < Cl < Br < I) in the development product fiubendiamide (54 ISO-proposed, Hal = I Nihon Nohyaku Co., Ltd./ Bayer Crop Science) [24], which activates selective ryanodine-sensitive intracellular Ca + release channels in insects as novel mode of action [25]. Introduction of a bulky and moderate lipophilic halogen such as iodine into 3-position of the phthalic acid aryl moiety increased the insecticidal activity considerably (Fig. 35.4) (for more details see Chapter 34). 

The increased lipophilicity (n), and a superior metabolic stability compared with the methyl analogue, often leads to an improved activity profile. Mono-fluorination and trifluorination of saturated aliphatic groups normally decrease lipophilicity, whereas higher fluoroalkyl groups (perfluoroalkyl groups) are introduced mainly to increase the lipophilicity [61], as recently shown for the 4 -perfluoro-iso-propyl-2-methyl-phenyl-amide fragment (4 -position halogen < fluoroalkoxy < CFj < C2 4-fluoroalkyl) in flubendiamide 54 ISO-proposed Nihon Nohyaku Co., Ltd./Bayer CropScience) (for more details see Chapter 31). 

Flubendiamide (54 ISO-proposed Nihon Nohyaku Co., Ltd./Bayer CropSdence) [125, 126,127] (Fig. 35.13) with a heptafluoro-isopropyl moiety in the anilide part of the molecule (Chapter 34) induces ryanodine-sensitive cytosoUc Ca + transients that were independent of extracellular Ca concentration in isolated neurons from the pest insect Heliothis virescens as well as in transfected CHO cells expressing the RyR from Drosophila mdanogaster. Binding studies on microsomal membranes from H. virescens flight muscle revealed that 54 interacts with a site distinct from the ryanodine binding site and disrupted the Ca + regulation of ryanodine binding by an allosteric mechanism. 

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