SPECTRUM

Chemical Fact Sheet

Chemical Abstract Number (CAS #) 5915413
CASRN 5915-41-3
SynonymsTerbuthylazine
1,3,5-Triazine-2,4-diamine, 6-chloro-N-(1,1-dimethylethyl)-N'-ethyl-
2-tert-Butylamino-4-chloro-6-ethylamino-s-triazine
Gardoprim
Primatol M
Analytical Method EPA Method 619
Molecular FormulaC9H16ClN5

Link to the National Library of Medicine's Hazardous Substances
Database for more details on this compound.

Use AS A HERBICIDE TO CONTROL WIDE RANGE OF WEEDS & AS PRE-EMERGENCE HERBICIDE IN SORGHUM (1.2-1.8 KG AI/HA); ALSO FOR SELECTIVE WEED CONTROL IN CITRUS, MAIZE, POD FORESTS & VINEYARDS /FORMER USE MIXED WITH TERBUMETON IT CONTROLS PERENNIAL WEEDS IN ESTABLISHED STANDS OF APPLES, CITRUS AND GRAPES. IT IS USED FOR NON SELECTIVE WEED CONTROL WHEN MIXED WITH SECBUMETON & IT IS ALSO USED IN COMBINATION WITH BROMOFENOXIM @ TOTAL AI RATES OF 0.8-1.25 KG/HA AS A BROAD SPECTRUM BROAD LEAVED HERBICIDE IN WINTER & SPRING CEREALS. /FORMER USE IN AFFORESTATION AREAS AND NONCROP SITUATIONS.
Apparent Color COLORLESS POWDER; WHITE SOLID
Melting Point 177-179 DEG C
Molecular Weight 229.7
Density 1.188 G/CU CM @ 20 DEG C
Environmental Impact Terbutylethylazine is not used in the US, but is used in Europe on various crops. If terbutylethylazine is released to soil, it will be expected to exhibit mobility in soil which can vary from high to low and therefore it may leach to groundwater. Terbutylethylazine may be subject to slow degradation in soil which may be due to both slow chemical hydrolysis and slow biodegradation based upon limited data for terbutylethylazine and other structurally related s-triazines. The half-lives for degradation of terbutylethylazine in Hatzenbuhl soil at pH 4.8 and Neuhofen soil at pH 6.5 are 84 and 170 days, respectively. The hydrolysis product is 2-hydroxy-4-tert-butylamino-6-ethylamino-1,3,5-triazine. The total concn of terbutylethylazine in treated forest soils decreased by a factor of approximately 2 over the course of one growing season. In greenhouse experiments with a sandy loam soil, the herbicidal activity decreased to a 50% level in 4.5 to 60 weeks at an application rate of 0.33 pounds/acre and >60 weeks at rates of 1.0 and 3.0 pound/acre; activity decreased to a 20% level in >60 weeks at all three application rates tested. It will not be expected to volatilize from near surface soils or surfaces. If released to water, terbutylethylazine will not be expected to bioconcentrate in aquatic organisms or to volatilize. It may adsorb to sediment and suspended particulate matter. The hydrolysis half-lives for terbutylethylazine is aqueous buffer solutions at 25 deg C at pH 5, 7, and 9 are 63, >200, and days, respectively. The rate of hydrolysis may be increased by various catalysts such as suspended soil. No data were located on the biodegradation of photolysis of terbutylethylazine in natural waters. If terbutylethylazine is released to the atmosphere, it will probably exist both in the vapor-phase and the particulate phase based upon a reported vapor pressure of 1.13X10-6 mm Hg. It may be subject to gas-phase reaction with photochemically produced hydroxyl radicals with an estimated half-life for this process of about 3.0 hr.
Environmental Fate TERRESTRIAL FATE: IT REMAINS LARGELY IN THE TOP SOIL. THE RELATIVE DEGREE OF PROTONATION & HYDROLYSIS OF VARIOUS S-TRIAZINES, INCLUDING TERBUTYLETHYLAZINE, BY CALCIUM-MONTMORILLONITE WAS ESTIMATED BY MEASUREMENT OF THE RELATIVE INTENSITIES OF IR BANDS & AFTER EXPOSURE OF FILMS OF CALCIUM-CONTMORILLONITE TO CHLOROFORM SOLN OF S-TRIAZINES FOR 2 WK. USE OF MATCHED FILMS OF CALCIUM-MONTMORILLONITE IN REFERENCE & SAMPLE BEAMS MADE IT POSSIBLE TO OBTAIN DIFFERENTIAL SPECTRA DUE ONLY TO ADSORBED S-TRIAZINE, ELIMINATING THE DIFFICULTY OF INTERFERENCE BY THE DEFORMATION BAND OF ADSORBED WATER ON CLAY. THE EFFECT OF SUBSTITUTIONS AT THE 2-, 4-, & 6-POSITIONS WAS ALSO STUDIED. IN GENERAL THE DEGREE OF PROTONATION & HYDROLYSIS DECR AS THE NUMBER OF CARBON ATOMS AT THE 4-, & 6-POSITIONS INCR. THESE OBSERVATIONS CAN AID IN PREDICTING THE BEHAVIOR OF S-TRIAZINES IN SOILS AS WELL AS IN FORMULATION CONTAINING SIMILAR MINERAL SURFACES. TERRESTRIAL FATE: If terbutylethylazine is released to soil, it will be expected to exhibit mobility in soil which can vary from high to low and therefore it may leach to groundwater. Terbutylethylazine may be subject to slow degradation in soil which may be due to both chemical hydrolysis and biodegradation based upon limited data for terbutylethylazine and other structurally related s-triazines. The half-lives for degradation (purportedly mainly soil catalyzed hydrolysis) of terbutylethylazine in Hatzenbuhl soil at pH 4.8 and Neuhofen soil at pH 6.5 are 84 and 170 days, respectively . The product of hydrolysis is 2-hydroxy-4-tert-butylamino-6-ethylamino-1,3,5-triazine . The rate of hydrolysis may be increased by various catalysts based upon the observed increase in rate of hydrolysis rates for the chemically similar herbicide atrazine in water solutions upon addition of sterilized soil and humic and fulvic acids . The total concn of terbutylethylazine in treated forest soils decreased by a factor of approximately 2 over the course of one growing season . In greenhouse experiments with a sandy loam soil, the herbicidal activity decreased to a 50% level in 4.5 to 60 weeks at an application rate of 0.33 pounds acre and >60 weeks at all three application rates tested(6). It will not be expected to volatilize from near surface soils or surfaces. AQUATIC FATE: If released to water, terbutylethylazine will not be expected to bioconcentrate in aquatic organisms or to volatilize. It may adsorb to sediment and suspended particulate matter. The hydrolysis half-lives for terbutylethylazine in aqueous buffer solutions at 25 deg C at pH 5, 7, and 9 are 63, >200, and >200 days, respectively . The rate of hydrolysis may be increased by various catalysts such as suspended soil . No data were located on the biodegradation of photolysis of terbutylethylazine in natural waters. ATMOSPHERIC FATE: If terbutylethylazine is released to the atmosphere, it will probably exist both in the vapor phase and the particulate phase based upon a reported vapor pressure of 1.13X10-6 mm Hg . It may be subject to gas phase reaction with hydroxyl radicals and photolysis. The rate constant for the vapor phase reaction of terbutylethylazine with photochemically produced hydroxyl radicals has been estimated to be 129.2 cu cm/molecule-sec at 25 deg C which corresponds to an atmospheric half-life of about 3.0 hr at an atmospheric concn of 5X10 5 hydroxyl radicals per cu cm . TERRESTRIAL FATE: THE LONG SOIL PERSISTENCE OF THESE CMPD DOES CREATE THE PROBLEM OF SOIL CARRY OVER, WHICH CAN DAMAGE SUCCEEDING CASH CROPS. THEREFORE EXTREME CAUTION MUST BE TAKEN IN THEIR APPLICATION ON CROPLAND TO AVOID SUCH INJURY TO FOLLOWING CROPS. TRIAZINES
Drinking Water Impact SURFACE WATER: Terbutylethylazine was detected in the following numbers of samples out of 708 total samples from Central European streams in spring 1976 to fall 1977 within the indicated concn ranges: 4 samples 1.1-10 ppb; 11 samples 0.4-1.0 ppb; 103 samples <0.4 ppb . Terbutylethylazine was found in Swedish stream waters (1985-1987) in 2 of 114 samples taken during June-July at a max concn of 0.7 ppb and not detected in 203 samples taken during April-May and Aug-Oct .

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