Investigations on herbicides II: 2‐Alkyloxy‐ and 2‐aryloxy ‐4,6‐dichloro‐1,3,5‐triazines 2‐Alkylthio‐ and 2‐arylthio‐4,6‐dichloro‐1,3,5‐triazines

Abstract

An improved synthesis of 4,6-dichloro-2-phenoxy-l,3,5.-triazine from cyanuric chloride and phenol in the presence of collidine (2,4,6-trimethylpyridine) induced us to investigate the scope and limitation of the substitution of one chlorine atom in cyanuric chloride and the influence of the base used as an acid acceptor. Phenols, thiophenols, alcohols, thiols and oximes generally reacted with cyanuric chloride in the presence of collidine giving good yields of the corresponding substitution derivatives. The herbicidal and fungicidal properties of the compounds are dealt with and are briefly discussed. The influence of the alkyl or aryl side chain on the biological activity was determined. For this reason some derivatives mentioned in the literature were included for comparison in our biological tests.From the 2-alkoxy-4,6-dichloro-l,3,5-triazines the methoxy and the ethoxy derivatives are known in the literature. These compounds were synthesized from cyanuric chloride and the corresponding alcohol in the presence of sodium bicarbonate2.s or by dropping a sodium meth-* ** 1 t J Present address: N.V.

Amino acids as chiral auxiliaries in cyanuric chloride‐based chiral derivatizing agents for enantioseparation by liquid chromatography

“…Brückner and Strecker (), for the first time, synthesized one of the MCT reagents, N 2 ‐[2‐(4‐chloro‐6‐methoxy‐1,3,5‐triazinyl)]‐ l ‐alanine amide (CMOT‐Ala‐NH 2 ), as described here (as a ready reference for the readers). For synthesis of CMOT‐Ala‐NH 2 , weighed amounts of l ‐Ala‐NH 2 (623 mg, 5 mmol) and 2,4‐dichloro‐6‐methoxy‐1,3,5‐triazine (0.9 g, 5 mmol; synthesized according to the procedure described by Koopman et al ., ), were dissolved in a mixture of acetone (15 mL) and water (10 mL), and a solution of NaHCO 3 (1.0 m , 15 mL) was added to it. The mixture was then stirred for 2 h at room temperature followed by neutralization with 0.1 m HCl and evaporation to dryness in vacuum.…”

Suzuki–Miyaura Coupling of Aryl Sulfonates with Arylboronic Acids Using a Morpholine–Pd(OAc)2 Catalyst System

“…Preparation of amphiphiles bearing the smaller hydrophobic segment was initiated by stepwise substitution from 2‐benzyloxy‐4,6‐dichloro[1,3,5]triazine,29 1 (Scheme ). Selective monosubstitution of 1 was achieved using either butylamine in tetrahydrofuran (THF) to give 4‐benzyloxy‐6‐chloro[1,3,5]triazin‐2‐yl)butylamine 2 en route to unsymmetrical amphiphiles 3 – 5 .…”

Sodium‐Ammonia Reductions in N‐Heteroaromatic Chemistry. Protodehalogenation and Protodealkylation of Sulphur Containing Pyrimidines, Pyridazines and S‐Triazines

“…The procedure described by Druey et al [17] for the synthesis of 3-chloro-6-mercaptopyridazine was found to be satisfactory when the reaction mixture was refluxed for 1 hr. instead of being run at room temperature, diethylamino-6-ethylthio-s-triazine [20] (B) and 2,4-bis-diethylamino-6-ethylthio-striazine (C) were synthesised from 2,4-dichloro-6-ethylthio-s-triazine [21] by methods analogous to those described by Declerck et al [4]. …”