Inhibition of Very-Long-Chain Fatty Acid Biosynthesis by 2-Chloro-N-(3-methoxy-2-thenyl)-2′,6′-dimethylacetanilide, Thenylchlor, and Its Analogs

Effect of fentrazamide on the growth, morphology and anatomy of Echinochloa crus-galli and Echinochloa oryzicola

“…Microscopic observation of cross sections treated with fentrazamide in this paper was similar to those of metolachlor 7) and butachlor. 14) Although chloroacetamides and oxyacetamides were described as inhibitors of both cell division and cell enlargement, 11,15) a recent study revealed that chloroacetamides like thenylchlor, 2-chloro-N-(2-ethyl-6-methylphenyl)-N-[(1-methylethoxy)methyl]acetamide 6) and chloroacetanilides including pretilachlor, 7) inhibited the biosynthesis of very long chain fatty acids (VLCFAs) as well as oxyacetamides, including mefenacet 8) and cafenstrole, N,N-diethyl-3-(2,4,6-trimethylphenyl)sulfonyl-1H-1,2,4-triazol-1-carboxamide). 8) Physiological and biochemical studies have shown that fentrazamide inhibited the formation of VLCFAs, similar to chloroacetamides and chloroacetanilides.…”

“…Fentrazamide inhibited the biosynthesis of very long chain fatty acids as well as chloroacetamides, oxyacetamides, including mefenacet, cafenstrole and thenylchlor. [4][5][6][7][8] Fedtke and Hess et al reported that the morphological effect of mefenacet on green algal cells was similar to that observed for thiocarbamates and chloroacetamides. 9) The macroscopic symptoms of mefenacet on E. oryzicola were dark green coloration, stunting of leaves, and strong growth inhibition of plants.…”

Structure-Activity Correlation of Very Long-Chain Fatty Acid Biosynthesis Inhibitors

“…Iso values of 10-7 to 10-6 M. However, inhibitory activity by the old type of thiolcarbamates, such as EPTC or prosulfocarb, was found rather weak, indicating an Iso value higher than 10-5 M (see Table 1 and Fig. 1: Couderchet et al 1998;Matthes et al 1998;Takahashi et al 2001aTakahashi et al ,b, 2002.…”

“…Recently, the structure and acyl-CoA elongation inhibitory activity of a new herbicidal chloroacetamide, thenylchlor, have been discussed (Takahashi et al 2001a). Introduction of a thenyl group (R, see Table 3) to the nitrogen atom of 2-chloro-2',6' -dimethylacetanilide (compound 1) gave a remarkable increase in both herbicidal activity assayed with barnyardgrass (Echinochloa oryzicola) and stearic acid elongation inhibition in the leek cell-free assay, irrespective of whether R is 2-thenyl or 3-thenyl group (compounds 2 and 3).…”

“…Interference with this fatty acid biosynthesis by herbicidal phenoxy-phenoxy propionic acids or cyclohexanediones is due to the inhibition of acetyl-CoA carboxylase, which explains their herbicidal mechanism of action (Devine et al 1993). It has been recently concluded that herbicidal chloroacetamides (e.g., alachlor), oxyacetamides (like mefenacet), carbamoylated five-membered nitrogen heterocycles (fentrazamide or cafenstrole), oxiranes (e.g., indanofan) and some miscellaneous compounds (ethofumesate or prosulfocarb) act as specific inhibitors of elongase(s) involved in the extraplastidic biosynthesis of very long-chain fatty acids (VLCFAs) with alkyl chains longer than CIS' although the precise mechanism of interaction of the compounds at the molecular level has not been clarified yet (Couderchet et al 1998;Matthes et al 1998;Boger et al 2000;Takahashi et al 2001a). The relationship between herbicidal action and elongase inhibition by the compounds mentioned above has been discussed in Chapter 6 (Boger and Matthes,Chap.…”