Synthesis and Structure-Activity Relationship of Newer Trichloromethyl-1, 3, 5-triazine Nitrification Inhibitors

Abstract

Various trichloromethyl-1, 3, 5-triazines were synthesized and effects of trichloromethyl-1, 3, 5-triazines on nitrification in the upland soil were investigated. 2-Substituted-4, 6bis(trichloromethyl)-1, 3, 5-triazines were prepared by trimerization or cotrimerization using CC13CN in the presence of Norton-Wakabayashi complex catalyst, e. g. A1Br3-HCI. 2-Amino-4-substituted-6-trichloromethyl-1, 3, 5-triazines were obtained through the haloform type of reactions of trichloromethyl-1, 3, 5-triazines with amines.The PI50 values of highly active trichloromethyl-1, 3, 5-triazines were 4. 5-5. 5. Essentially they have a CC13-group and an amino or alkylamino group in the three substituents of 1, 3, 5-triazine ring. QSAR between pI55 values and log P(S) parameters were investigated by multi-parameter regression analysis. Hydrophobic parameters, log P(S) estimated by semi-empirical calculation, were used for convenience instead of log P(H) determined by HPLC in this QSAR study.The optimum log P(S) was calculated as 2.91, a little more hydrophobic figure compared with the log P value (ca. 2.4) in our previous paper.By the use of this value, it will become possible to design highly active trichloromethyl-1, 3, 5-triazine nitrification inhibitors.

Synthesis and Herbicidal Activity of 2-Benzylamino-4-methyl-6-trifluoromethyl-1, 3, 5-triazune Derivatives

“…[1][2][3][4][5] In the course of our synthetic and bioassay programs of the 2-aralkylamino-1, 3, 5-triazines derived from 2-trichloromethyl-1, 3, 5-triazines, new 2-benzylamino-4-methyl-6-trifluoromethyl-1, 3, 5-triazines have been found to exhibit a herbicidal activity. This paper reports the synthesis and the effect by the structural modification of the 2-aralkylamino-1, 3, 5-triazine derivatives on the herbicidal activity and PET inhibitory activity.…”

Mode of Action and QSAR Studies of Nitrification Inhibitors

“…Regression analysis were performed between P'50 values obtained from ATCC 25978 or TK 794 and hydrophobic parameters (log P) determined by Okano et al 8) The log P values of 1, 3, 5-triazine derivatives was estimated by a semi-empirical method based upon the additive property of the n value. As a first step the log P (log P-1) values of twelve 2, 4, 6-trisubstituted-l, 3, 5-triazines were determined by the HPLC method using an ODS column (Inertsil ODS 4.6 X 250 mm) and methanol-water (8 ; 2) as the mobile phase.l4) From log P-1 values we estimated the log P values for 1, 3, 5-triazine (log P = 2.69) using the r (R1), n (R2) and n (R3) values of Nys & Rekker15 according to the Eq.…”

“…In 1969 Wakabayashi & Okuzu reported the nitrification inhibitory activity of 2-amino-4-methyl-6-trichloromethyl-l, 3, 5-triazine.3-6 Recently Murakami et al 7 and Okano et al 8 systematically synthesized a large number of 1, 3, 5-triazine type nitrification inhibitors and found a good correlation between nitrification inhibitory activity in soil and the hydrophobic parameter, log octanol-water partition coefficient (log P) of the triazines synthesized. Takagi et al9 using Nitrosomonas europaea ATCC 25978 and Nitrobacter agilis ATCC 14123, concluded that some of these compounds inhibited the ammonia oxidizing process but not the nitrite oxidation.…”