Benzenedicarboxamides

CN 5-[acetyl(2,3-dihydroxypropyl)amino]-A/,/V-bis(2,3-dihydroxypropyl)-2,4,6-triiodo-l,3-benzenedicarboxamide... 

N 2-[l,l-dimethyl-2-(methylsulfonyl)Ethyl-3-iodo-N1-[2-methyl-4-[ll2l2l2-tetrafluoro-l-(trifluoromethyl)Ethyl) Phenyl-1,2-benzenedicarboxamide... 

Flubendiamide, a benzenedicarboxamide insecticide, also affects calcium channels. This insecticide induces unique symptomology in poisoned insects, showing a gradual contraction of the insect body. It is believed that flubendiamide induces intracellular Ca2+ release mediated by a calcium channel such as the ryanodine receptor resulting in the contraction of insect muscle (Tohnishi et al., 2005 Ebbinghaus-Kintscher et al., 2006 Nauen, 2006). 

BENZENEDICARBOXAMIDE, N,N -DLMETHYL-N,N -DINITROSO-(9CI) see DR0400 o-BENZENEDICARBOXYUC ACID see PHW250 p-BENZENEDICARBOXYLIC ACID see TAN750 BENZENE-1,2-DICARBOXYLIC ACID see PHW250... 

Tetraethylammonium bromide Tetraethylammonium chloride Tetraethylammonium iodide 1,2,3,5-Tetraethylbenzene A/,A/,A/, A/-Tetraethyl-1,2-benzenedicarboxamide... 

Resistance has often been a problem or a potential problem for insecticides and this is one of the most important reasons why the insecticides with a new mode of action have been always desired, though it is quite a difficult task to find such molecules. Flubendiamide, discovered by Nihon Nohyaku (NNC), is a novel insecticide belonging to the new chemical class of 1,2-benzenedicarboxamides or phfhalic diamides, having a unique chemical structure (Figure 1) [1-3], Flubendiamide is co-developed by NNC and Bayer CropScience globally [4], The structure-activity relationships, the chemistry, including topics in process research, the mode of action and the biological profiles are described. 

Figure 2 shows the early phase of research for flubendiamide. In 1989, Dr. T. Tsuda, at Osaka Prefecture University in Japan, reported that some pyrazinedicarbox-amide derivatives showed moderate herbicidal activity [5]. From 1990, the research for herbicide discovery was conducted at NNC Research Center. In the course of this research, a lead compound for an insecticide was discovered in 1993 from the class of benzenedicarboxamides as shown in Figure 2. This compound provided insecticidal activity on lepidoptera at the relatively high dose of 50-500 mg a.i./L. Moreover, it did not show activity against other species such as Hemiptera or Aca-rina. Although the level of activity was not satisfactory, this compound attracted the attention of researchers for both the novelty of its chemical structure and the characteristic insecticidal symptoms such as gradual contractions of the insect body. We therefore started the study for further optimization of this lead compound.

The chemical structure of benzenedicarboxamides can be divided into three parts as shown in Figure 3. These are characterized by (A) the phthaloyl moiety, (B) the aliphatic amide moiety and (C) the aromatic amide moiety. A brief description of the structure-activity relationships for each part is described below. 

Table I shows the insecticidal activity of 1,2-benzenedicarboxamides. Insecticidal activities are shown as EC5Q values against common cutworm Spodoptera litura) and diamondback moth Plutella xylostdla).

Table I. Insecticidal activities of 1,2-benzenedicarboxamides against Spodoptera iitura and Piuteiia xylostella.

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