Azido-s-triazines

Herbicides that seem to have a single site of action on the photochemical pathway, which is associated closely with photosystem 11 are the chlorinated pheny 1 ureas, Ws-carbamates such as phenmedipham, chlorinated s-triazines, substituted uracils, pyridazinones, diphenylethers, 1,2,4-triazinones, azido-s-triazines, cyclopropane-carboxamides, p-alkylanilides, p-alkyl-thioanilides, aminotriazinones, and urea-carbamates (2). 

Azido-s-triazines break down quickly in the soil. 

Azide ion is a rather weak nitrogen nucleophile, but in aqueous acetone (20°, 5 min) it readily produces 2-azido-4,6-dichloro-s-triazine (330) and also yields more slowly (0°, 12 hr, 90% yield) the 2,4,6-triazido-s-triazine. The latter is rapidly hydrolyzed (50°) to cyanuric acid and is easily mono-aminated (0°, 1 hr, in ether). 

Fluorine and chlorine are the only important choices for the labile substituents on a heterocyclic reactive system but numerous other leaving groups have been patented, mostly as substituent on an s-triazine ring. These include sulpho, cyano, thiocyanato, azido and trichloromethyl [26], as well as more elaborate groupings (Figure 7.2). Such derivatives are... 

Azido-4-ethylamino-6-t-butylamino-s-triazine (WL 9385,35) is efficient for the selective control of dicotyledonous weeds in grain, maize and potato. 2-Azido-4-isopropylamino-6-methylthio-i-triazine (aziprotryne, 36) is a selective herbicide efficient in the control of certain dicotyledonous weeds in cabbage, bean, sunflower, onion and maize, as is 2-azido-4-jec-butylamino 6-methylthio-j-triazine (C 8250, 37) in soybean and cotton. 

Azido-N-(1-methylethyl)-6-methylthio-1,3,5-triazin-2-amine. Azeprotryne 2-Azido-4-isopropylamino-6-methylthio-s-triazine 2-Azido-4-isopropylamino-6-methylthio-1,3,5-triazine 4-Azido-N-(1-... 

Triazene, 1,3-diphenyl. See Diazoaminobenzene S-Triazine, 2-azido-4-(isopropylamino)-6-(methylthio)-. See Aziprotryn s-Triazine, 2-(t-butylamino)-4-chloro-6-(ethylamino)-. See Terbuthylazine s-Triazine, 2-(t-butylamino)-4-(ethylamino)-6-(methylthio)-. See Terbutryn s-Triazine, 2-chloro-4-(diethylamino)-6-(ethylamino)- 1,3,5-Triazine-2,4-diamine, 6-chloro-N,N,N -triethyl-. See Trietazine S-Triazine-2,4-(1 H,3H)-dione, 3-cyclohexyl-6-(dimethylamino)-l-methyl-. See Hexazinone s-Triazine, hexahydro-1,3,5-trinitroso-. See Hexahydrotriazine... 

Azidoatrazine ([ " C]-2-azido-4-ethylamino-6-isopropylamino-s-triazine), a derivative of herbicide atrazine which binds to the secondary plastoquinone electron-acceptor site of photosystem 2 (PS2), was used for photoafiinity labeling followed by sequence analysis of peptides derived by proteolysis of the PS2 centers [110]. 

G. Bueher, F. Siegler, J.J. Wolff, Photochemistry of 2-azido-4,6-dichloro-s-triazine matrix isolation of a strained cyclic carbodiimide containing four nitrogen atoms in a seven-membered ring, J. Chem. Soc. Chem. Commun., 1999,2113-2114. 

Nitrogen, Sulphur and Selenium-containing Compounds. - The S- and 6-substituted 3-amino-l,2,4-triazines 5 and 6, the spiro-naphthoxazine 7, the hetero Diels-Alder cycloadduct 8, 5-azido-3-0-benzyl-6-0-tert-butyldiphenylsilyl-5-deoxy-1,2-O-isopropylidene-P-L-talofuranose, 9 5-azido-6-0-benzoyl-3,5-dideoxy-3-fluoro-l,2-<9-isopropylidine-a-D-glucofuranose, kedarosamine (2,4-dideoxy-4-dimethylamino-L-fucopyranose) as the 3-0-(4-bromobenzoyl) derivative. 1,2 5,6-Di-0-isopropylidene-a-D-ribohexos-3-ulose phenylhydrazone, p-iactam 9 (from a diastereoselective [2+2] cycloaddition to a carbohydrate-based arylimine), 3 the D-arabino and D-ribo lactam derivatives 10 and 11, " the fully-protected iminosugar 12, 5 2,3,4,5-tetra-0-acetyl-6-amino-6-deoxy-D-mannonolactam, 4,8-anhydro-3-... 

Kayama, R., Shizuka, H., Sekiguchi, S., and Matsui, K., Photochemical reactions of azido-1,3,5-triazines with hydrocarbons and ketones. Bull. Chem. Soc. pn., 48, 3309,1975. 

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