Synthesis and biological potency of anilino-triazine insecticides was written by Johnson, Timothy C.;Brown, Annette V.;Bryan, Kristy K.;Guenthenspberger, Katherine K.;Hunter, Ricky;Martin, Timothy P.;Niyaz, Noormohamed;Tisdell, Gene F.;Trullinger, Tony. And the article was included in Pest Management Science in 2017.Category: chlorides-buliding-blocks The following contents are mentioned in the article:
BACKGROUND : An insecticide screening effort identified N-(4-bromophenyl)-4,6-bis(2,2,2-trifluoroethoxy)-1,3,5-triazine-2-amine as having weak potency against two lepidopteran species, Helicoverpa zea and Spodoptera exigua. A structure-activity relationship study about the trifluoroethoxy substituents and the aniline of this compound was carried out in an effort to improve insecticidal potency. RESULTS : Initially, a series of analogs bearing various substituents on the aniline were prepared, and the insecticidal potency was evaluated against H. zea and S. exigua in greenhouse diet feeding assays. The results showed that electron-withdrawing substituents, such as Cl, Br and CF3, were preferred over electron-donating substituents, such as methoxy, and that potency was significantly better when the substituent was in the para-position. Addnl. investigations showed that bis(anilino)trifluoroethoxytriazines were more potent. Replacement of the remaining trifluoroethyl group in the bis(anilino)triazine series with an alkyl amine lead to compounds of equal or superior efficacy. CONCLUSION : The work presented showed that electron-withdrawing substituents in the para-position of the aniline ring of the initial hit delivered the best levels of insecticidal potency against the two insect species tested. Further investigations showed that potency could be improved by replacing one of the two trifluoroethoxy groups with addnl. 4-substituted aniline. This study involved multiple reactions and reactants, such as 4,6-Dichloro-N-phenyl-1,3,5-triazin-2-amine (cas: 2272-40-4Category: chlorides-buliding-blocks).
4,6-Dichloro-N-phenyl-1,3,5-triazin-2-amine (cas: 2272-40-4) belongs to organic chlorides. Chlorinated organic compounds are found in nearly every class of biomolecules and natural products including alkaloids, terpenes, amino acids, flavonoids, steroids, and fatty acids. Alkyl chlorides readily react with amines to give substituted amines. Alkyl chlorides are substituted by softer halides such as the iodide in the Finkelstein reaction.Category: chlorides-buliding-blocks
Referemce:
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics