Facile Synthesis And Biological Activities Of Novel Organic Salts Of N-nitro-2,4,6-trifluoroaniline

Many patents reported that N-nitro trisubstituted aniline is a kind of double-function chemical compound which have herbicidal activity, antibacterial and plant growth regulating activity. Our research group synthesised N-nitro-2,4,6-trifluoroaniline though non-acidic nitrification system nitrifing arylamine, which is better plant growth regulating activity, and is better than others tri-substituted N-nitro aniline. Therefore, this article study on plant growth regulating activity of N-nitro-2,4,6-trifluoroaniline salt compounds,in order to develop the green, efficient, low-residue pesticide. Structural formula of the title compounds are as follows:Synthesis and characterization of N-nitro-2,4,6-trifluoroaniline salt:The N-nitro-2,4,6-trifluoroaniline turning into salt and ion exchange will get twenty-two new N-nitro-2,4,6-trifluoroaniline organic salts and the target compounds were characterized by IR, 1HNMR.Biological evaluation of N-nitro-2,4,6-trifluoroaniline salts:(1) NTFA salts were found better growth-promoting activity in low concentrat- ions,and better inhibitory effect in high concentrations; At 10mg/L, better growth-promoting activity on rice, barley, wheat, and better inhibitory effect on the root length of Chinese cabbage, radish, cabbage and ryegrass, especially the inhibition rate of Chinese cabbage root substantially reach above 50%; By analyzing the compound structure, long-chain(C≥8) alkyl amine salts with N-nitro-2,4,6 trifluoroaniline were better inhibitory effect than short-chain alkyl ammonium salts in root.(2) Through plant growth regulating activity tests, we found that compound 1a, 2a,2b, 3f, 3k and 3t can effectively promote root growth and increase fresh weight of rice, at1mg/L, compound 2a, 2b reach A level for rice root, at 0.1mg/L and 2.5mg/L, also reach B level, the effects were better than the group of CCC; and stem of rice become dwarf and thicken, 2b and 3k exceed the original drug group of CCC at 5mg/L; According to the experimental data it can be speculated that the growth-promoting effect of N-nitro compound salts main act by N-nitro part and ammonium part, which promote root effect is much better than a single amine salt group, and the ammonium part main promote riceroot, increase tillering rate, prompting fibrous root growth, while N-nitro part promote taproot growth and dwarf stems.(3) By testing the biological activity we found that compounds 1a, 3a, 3e, 3j, 3m, 3p,3k and 3q has good herbicidal activity and inhibition of dicotyledonous is better than monocotyledons, which has a good selectivity, especially it is best inhibition effect for rape, IC50 ≤10 mg/L of the root, IC50 of 3p can reach to 0.41mg/L; Except that, we found IC50 of 3p for ALS enzyme in vivo(rice) and enzyme levels both close to 5mg/L, So we can speculate the long chain alkyl ammonium of NTFA compounds may has a certain inhibitory effect for ALS enzyme, and can be further studied as a target enzyme.