Chloro triazines atrazine

Lamoureux, G.L., Shitnabukuro, R.H., Swanson, H.R., and Frear, D.S. Metabolism of 2-chloro-4-ethylamino-6-isopropylamino-s-triazine (atrazine) in excised sorghum leaf sections, / Agric. Food Chem., 18(l) 81-86, 1970. 

When rats were administered atrazine in drinking water at 0.1, 0.2, or 0.5 g/1 for 1 or 3 weeks, they excreted as the principal metabolite 2 -chloro-4-ethylamino-6-amino-s-triazine. Atrazine and its metabolites have been shown to alter the activity of some testosterone-metabolizing enzymes in the rat pituitary and hypothalamus and to decrease hormone-receptor binding in the prostate. ... 

Members of an extensive group of sym-triazine herbicides, usually having one or two secondary amine substituents, block the Hill reaction and inhibit photosynthesis in a manner quite similar to that of the urea herbicides. The most widely used, 2-chloro-4-(ethylamino)-6-(isopropylamino)-s-triazine (atrazine), (10), is one of several hundred herbicidal analogs... 

The metabolism of individual chloro- -triazines has been the subject of renewed research in plants as a result of the reregistration process initiated by the United States Environmental Protection Agency (USEPA) in the form of data-call-ins for new study requirements. Atrazine was chosen as a model compound for this class of. v-triazines because completed research on several crops has greatly expanded our knowledge of the original pathway (Figure 7.1) as proposed by Lamoureux et al. (1973). 

Hormann, W.D., Eberle, D.O. (1972) The aqueous solubility of 2-chloro-4-ethylamino-6-isopropylamino-l,3,5-triazine (atrazine) obtained by an improved analytical method. Weeds Res. 12, 199-202. 

To optimize MIPs for the two triazines ametryn (an S-triazine) and atrazine (a chloro triazine) Takeuchi et al. prepared a library of imprinted terpolymers, using... 

Among the 2-chloro-4,6-bis(alkylamino)-i-triazines with two different substituent side-chains, 2-chloro-4-ethylamino-6-isopropylamino-i-triazine (atrazine, 8) is the most active, and followed, in decreasing order of activity, by 2-chloro-4-ethylamino-6-5ec-butylamino-i-triazine (sebuthylazine, 9) and 2-chloro-4-ethyl-amino-6-/-butylamino-j-triazine (terbuthylazine, 10). 

The metabolism of chloro-S-triazines in soil involves reactions of dealkylation, deamination, hydroxylation, and ring cleavage [171]. Dealkylation of chloro -triazines does not remove their toxidly, which has been, instead, attributed to the release by chemical hydrolysis of active chknine [172]. In a study on the effects of atrazine and its degradation products on phototrophic microorganisms, the most toxic degradation product was deethylated atrazine, vdiidi was 2 to 7 times more effective towards cyanobacteria than deisopropylated atrazine. On the contrary, diamino and hydro atrazine were non-toxic [173]. 

Azomethine group (>C=N-) containing compounds cyolane, cytrolane, chlordimerform, drazoxolon s-Triazines atrazine Chlorinated compounds 2,4-D (2,4-dichlorphenoxyacetic acid), propachlor (2-chloro-A/-2-propylacetanilide), pentachlorophenol, picloram (4-amino-3,5,6-trichloropicolinic acid), hexachlorocyclohexane Nitro-group-containing compounds metaphos (o,o-dimethyl-o-(4-nitrophenyl) thiophosphate, parathion, paraoxon... 

Triazines. Triazine herbicides are one of several herbicide groups that are heterocycHc nitrogen derivatives. Triazine herbicides include the chloro-, methylthio-, and methoxytriazines. They are used for the selective pre-emergence control and early post-emergence control of seedling grass and broadleaved weeds in cropland (299). In addition, some of the triazines, particularly atrazine, prometon [1610-18-0] and simazine [122-34-9] are used for the nonselective control of vegetation in noncropland (2). Simazine may be used for selective control of aquatic weeds (2). 

More controversially, endocrine disruption as a consequence of exposure to the herbicide atrazine (2-chloro-4-ethylamine-6-isopropylamine-s-triazine), one of the most widely used herbicides in the world, has also been hypothesized to explain various adverse biological effects in frog populations in the United States. Exposure to atrazine in the laboratory at high concentrations, far exceeding those found in the natural environment, has been reported to induce external deformities in the anuran species Rana pipiens, Rana sylvatica, and Bufo americanus (Allran and Karasov 2001). Studies by Hayes et al. have suggested that atrazine can induce hermaphroditism in amphibians at environmentally relevant concentrations (Hayes et al. 2002 Hayes et al. 2003). Laboratory studies with atrazine also indicated the herbicide... 

Combined treatment of atrazine with ozone and H2O2 resulted in retention of the triazine ring, and oxidative dealkylation with or without replacement of the 2-chloro group by hydroxyl (Nelieu et al. 2000). Reaction with ozone and hydroxyl radicals formed the analogous products with the additional formation of the acetamido group from one of the N-alkylated groups (Acero et al. 2000). 

A number of substituted triazines are used as herbicides, and their biodegradation has been discussed in Chapter 10, Part 1. Treatment of soil contaminated with atrazine (2-chloro-4-(ethylamino)-6-isopropylamino-l,3,5-triazine) illustrated a number of significant features. Although the soil that was used had the potential for degradation, a laboratory experiment with Pseudomonas sp. strain ADP that had an established potential for atrazine degradation revealed important limitations. There was a substantial decline in the numbers of Pseudomonas sp. strain ADP and only limited mineralization. Supplementation with citrate or succinate increased the survival of the strain, and successful mineralization was dependent on the preservation of a carbon/nitrogen ratio >10 (Silva et al. 2004). The last would apply generally to substrates with a low C/N ratio such as triazines. 

Cotterill [100] studied the effect of ammonium nitrate fertilizer on the electron capture or nitrogen specific gas chromatographic determination of Triazine plus other types of herbicide (Atrazine(2-chloro-4-ethylamino-6-isopropylamino, 1,3,5 triazine), Simazine (2-chloro-4.6 bis ethyl amino 1,3,5 triazine), Linuron (3,4,-chlorophenyl-l-methoxy-l-methyl urea), Metribuzin, Triallate and Phorate) residues in soil. 

Acetamido-4-amino-6-chloro-s-triazine, see Atrazine Acetanilide, see Aniline, Chlorobenzene, Vinclozolin Acetic acid, see Acenaphthene, Acetaldehyde, Acetic anhydride. Acetone, Acetonitrile, Acrolein, Acrylonitrile, Aldicarb. Amyl acetate, sec-Amyl acetate, Bis(2-ethylhexyl) phthalate. Butyl acetate, sec-Butyl acetate, ferf-Butyl acetate, 2-Chlorophenol, Diazinon. 2,4-Dimethylphenol, 2,4-Dinitrophenol, 2,4-Dinitrotoluene, 1,4-Dioxane, 1,2-Diphenylhydrazine, Esfenvalerate. Ethyl acetate, Flucvthrinate. Formic acid, sec-Hexyl acetate. Isopropyl acetate, Isoamyl acetate. Isobutyl acetate, Methanol. Methyl acetate. 2-Methvl-2-butene. Methyl ferf-butvl ether. Methyl cellosolve acetate. 2-Methvlphenol. Methomvl. 4-Nitrophenol, Pentachlorophenol, Phenol. Propyl acetate. 1,1,1-Trichloroethane, Vinyl acetate. Vinyl chloride Acetoacetic acid, see Mevinphos Acetone, see Acrolein. Acrylonitrile. Atrazine. Butane. 

Acetylamino-4-amino-6-chloro-yV-(l-methylethyl) -s-triazine, see Atrazine... 

Amino-4-chloro-6-hydroxy-s-triazine, see Atrazine 2-Amino-4-chlorophenol, see Chlorpropham. 

Amino-4-hydroxy-6-chloro-s-triazine, see Atrazine 4-Amino-3-hydroxy-5,6-dichloropicolinic acid, see... 

Chloro-4-amino-s-triazine, see Atrazine Chloroaniline, see Linuron. Monuron... 

Chlorocatechol, see 4-Chlorophenol. 2,4-D, 2,4,5-T 4-Chloro-o-cresol, see MCPA 2-Chloro-4,6-diamino-s-triazine, see Atrazine. 

Chloro-4,6-dihydroxy-s-triazine see Atrazine 4-Chloro-2,5-dimethoxybenzenamine, see Atrazine A-Chlorodimethylamine, see Dimethylamine Chloroethane, see 1,1,1-Trichloroethane,... 

Trichloroethylene 2-Nitroaniline 2-Chloroethanol, see 1,2-Dichloroethane TV-Chloroethanolamine, see Ethanolamine 2-(2-Chloroethoxy)ethanol, see Bis(2-chloroethyl) ether 2-Chloro-4-(ethylamino)-6-amino-s-triazine, see Atrazine... 

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