Studies On The Synthesis And Bioactivity Of Novel Aryloxyphenoxy Carboxylic Acid Derivatives Compounds

Aryloxyphenoxy propanoic derivatives are effective herbicides which are successfully explored for agriculture and forestal production first. They have high herbicidal activities for grassy weed as the figure. Many pesticide companies are interested in these compounds and herbicides are decorated and rebuilt which is based on their original structural mode, leading to the discovery of noval herbicides. Benzonic ring was changed to heterocyclic ring to formed a serie of high efficient pesticides, for instance, Uizalofop(which was producted by japan Nissan Chemical Ind. Co. Ltd), Fenoxaprop-ethyl、Fenthiaprop-ethyl (which was produced by Hoechst Ind. Co. Ltd), Haloxyfop-R-methyl (which was produced by Dow Ind. Co. Ltd).The compound HNPC-A8169 which was synthesized by the department of Hunan Branch of National Pesticide R&D South Center, Hunan Research Institute of Chemical Industry showed excellent insecticidal activity and herbicidal activity. We designed 23 compounds of 5 series with HNPC-A8169 as leading compound by methods of bioisosteris and so on. The structure of the designed compounds were confirmed by IR、LC/MS、1H NMR. The biological activity of them was tested by the Standard Operation Procedure of the bioassay department of Hunan Branch of National Pesticide R&D South Center.(Ⅰ)2-(4-(5-(trifluoromethyl)pyridin-2-yloxy)phenoxy)propanamide derivatives. (8 compounds) (Ⅱ)2-(4-(3,5-dichloropyridin-2-yloxy)phenoxy)propanamide derivatives. (4 compounds)(Ⅲ)2-(4-(5-chloro-3-fluoropyridin-2-yloxy)phenoxy)propanamide derivatives. (4 compounds)(Ⅳ)2-(4-(3-chloro-5-(trifluoromethyl)pyridin-2-yloxy)phenoxy)propanamide derivatives. (5 compounds)(Ⅴ)2-(4-(6-chloropyridazin-3-yloxy)phenoxy)propanamide derivatives. (2 compounds)Biological assay:A. Hebicidal activity:The target compounds exhibited very good herbicidal activities. With the dosage of 75 g/ha, all the target compounds exhibited A level herbicidal activities to monocotyledonous herbs(Digitaria sanguinalis, Echinochloa crus-galli and Setaria viridis) besidesⅠ-4h whose activity is low;Ⅲ-4b、Ⅳ-4b、Ⅴ-4a、Ⅴ-4b which had not been tested up to now. It must be noted that,Ⅰ-4e andⅡ-4a also showed A level herbicidal activity to dicotyledonous plants (Abutilon theophrasti, Chenopodium album and Amaranthus ascedense). B. Fungicidal activity:The target compounds exhibited poor herbicidal activities. ButⅠ-4d andⅠ-4e exhibited A level bactericidal activity to Sclerotonia sclerotiorum.C. Insecticidal activity:The target compounds exhibited poor herbicidal activities. The inhibition rates for all the test insects were less than 50%。...