Tralkoxydim
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Tralkoxydim
structure -
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CAS No:
87820-88-0
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Formula:
C20H27NO3
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Chemical Name:
Tralkoxydim
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Synonyms:
2-Cyclohexen-1-one,2-[1-(ethoxyimino)propyl]-3-hydroxy-5-(2,4,6-trimethylphenyl)-;2-[1-(Ethoxyimino)propyl]-3-hydroxy-5-(2,4,6-trimethylphenyl)-2-cyclohexen-1-one;Tralkoxydim;PP 604;FD 4026;Grasp;ICI-A 604;Achieve;Achieve (pesticide);Splendor;ICIA 0604;Grasp (cyclohexenone);2-[1-(Ethoxyimino)propyl]-3-hydroxy-5-mesitylcyclohex-2-enone;115839-88-8
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CAS No:
Tralkoxydim Basic Attributes
329.43
329.43
618-075-9
DTXSID1034973
Off white to pale pink solid|Colorless solid
2914509011
Characteristics
55.4
4.46 (non-ionized)
an odorless, beige liquid
1.16 g/cu cm (dry); 1.13 g/cu cm (wet)
106 °C
457.1±55.0 °C at 760 mmHg
>100 °C
1.547
In water (20 deg C) = 5 mg/l (pH 5), 6.7 mg/l (pH 6.5), 9800 mg/l (pH 9)
0-6°C
2.78X10-9 mm Hg @ 20 deg C
LD50 orally in male and female rats, male and female mice, male rabbit (mg/kg): 1324, 934, 1231, 1100, 519; dermally in male and female rats: >2000, >2000 mg/kg (Warner 1987)
Faint burnt odor
pH = 5.3 at 22 °C
pKa = 4.98 @ 25 °C
Hydrolysis half-life of 6.3 days (pH 5), 114 days (pH 7), 1594 days (pH 9)
Non-corrosive
Safety Information
9
UN 3077 9 / PGIII
3
22
GW7191600
Xn
Stable a normal warehouse temperature. Non-corrosive.
P273-P301 + P312 + P330-P391-P501
H302-H351-H411
Toxicity
LD50 Rat (male) oral 1324 mg/kg|LD50 Rat (female) oral 934 mg/kg|LD50 Mouse (male) oral 1231 mg/kg|LD50 Mouse (female) oral 1100 mg/kg|For more Non-Human Toxicity Values (Complete) data for TRALKOXYDIM (7 total), please visit the HSDB record page.
Tralkoxydim's production may result in its release to the environment through various waste streams; it's use as a herbicide(1) will result in its direct release to the environment(SRC).
TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc of 8,100(SRC), determined from a structure estimation method(2), indicates that tralkoxydim is expected to be immobile in soil(SRC). Koc values of 1,800, 1,530, and 28 can also be estimated(SRC), using water solubilities of 5 mg/l (pH 5), 6.7 mg/l (pH 6.5), and 9,800 mg/l (pH 9)(3), respectively, and a regression-derived equation(4); according to the classification scheme(1), these estimated Koc values suggest that tralkoxydim will have low mobility at pH 5 and pH 6.5 and very high mobility at pH 9(SRC). Volatilization from moist soil surfaces is not expected to be an important fate based on an estimated Henry's Law constant of 2.41X10-10 atm-cu m/mole(SRC), derived from its vapor pressure, 2.78X10-9 mm Hg at 20 °C(3), and water solubility, 5 mg/l(3). The hydrolytic degradation half-life of tralkoxydim in water is 6.3 days at pH 5, 114 days at pH 7, and 1594 days at pH 9(5); therefore, hydrolysis may be an important degradation process in moist acidic soils(SRC). On soil surfaces, tralkoxydim rapidly photolyzes with a half-life of 2.4 days(5). In field dissipation studies in Illinois, Montana, Washington and Canada, the parent tralkoxydim dissipated rapidly with half-lives ranging from <1 to 35 days(5). Soil dissipation half-lives of 3 days (aerobic soil, 20 °C) and 25 days (flooded soil) have also been reported(3).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc of 8,100(SRC), determined from a structure estimation method(2), indicates that tralkoxydim is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 2.41X10-10 atm-cu m/mole(SRC), derived from its vapor pressure, 2.78X10-9 mm Hg at 20 °C(4), and water solubility, 5 mg/l(4). According to a classification scheme(5), an estimated BCF of 540(SRC), from a log Kow of 4.46(8), and a regression-derived equation(6) suggests the potential for bioconcentration in aquatic organisms is high(SRC). However, tralkoxydim residue bioaccumulation was relatively low in bluegill sunfish exposed in a flow-through system for 28 days(7). The hydrolytic degradation half-life of tralkoxydim in water is 6.3 days at pH 5, 114 days at pH 7, and 1,594 days at pH 9(7); therefore, hydrolysis may be an important degradation process in acidic waters(SRC). Tralkoxydim is not resistent to photodegradation in water with a calculated half-life of 19.3 days(7). The anaerobic aquatic metabolism half-life is reported to range from 47 to 115 days(7).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), tralkoxydim, which has a vapor pressure of 2.78X10-9 mm Hg at 20 °C(2), will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase tralkoxydim is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 2.5 hours(SRC), calculated from its rate constant of 1.54X10-10 cu cm/molecule-sec at 25 °C(SRC), that was derived using a structure estimation method(3). Particulate-phase tralkoxydim may be removed from the air by wet and dry deposition(SRC).
The aqueous hydrolysis half-life of tralkoxydim has been calculated to be 6.3 days at pH 5, 114 days at pH 7, and 1594 days at pH 9(1). Tralkoxydim is not resistent to photodegradation in water with a calculated half-life of 19.3 days(1). On soil surfaces, tralkoxydim rapidly photolyzed with a corrected half-life of 2.4 days(1).|The rate constant for the vapor-phase reaction of tralkoxydim with photochemically-produced hydroxyl radicals has been estimated as 1.54X10-10 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 2.5 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1).
An estimated BCF of 540 was calculated for tralkoxydim(SRC), using an experimental log Kow of 4.46(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is high(SRC).|Tralkoxydim residue bioaccumulation was relatively low in bluegill sunfish exposed in a flow-through system for 28 days(1).
Soil adsorption/desorption data indicate that tralkoxydim and its degradates can be very mobile in soil(1).|Using a structure estimation method based on molecular connectivity indices(1), the Koc for tralkoxydim can be estimated to be 8113(SRC). According to a classification scheme(2), this estimated Koc value suggests that tralkoxydim is expected to be immobile in soil. Koc values of 1800, 1530 and 28 can also be estimated(SRC), using water solubilities of 5 mg/l (pH 5), 6.7 mg/l (pH 6.5) and 9800 mg/l (pH 9)(3), respectively, and a regression-derived equation(4). According to the classification scheme(2), these estimated Koc values suggest that tralkoxydim will have low mobility at pH 5 and pH 6.5 and very high mobility at pH 9(SRC).
The Henry's Law constant for tralkoxydim is estimated as 2.41X10-10 atm-cu m/mole(SRC) derived from its vapor pressure, 2.78X10-9 mm Hg at 20 °C(1), and water solubility, 5 mg/l(1). This Henry's Law constant indicates that tralkoxydim is expected to be essentially nonvolatile from water surfaces(2).
Occupational exposure to tralkoxydim may occur through inhalation of dust and dermal contact with this compound at workplaces where tralkoxydim is produced or used. (SRC)
Drug Information
Mode of action: Selective systemic herbicide, absorbed by the leaves & translocated acropetally in the phloem to the growing points where it inhibits cell division.|Based on the results of the hamster & rat metab studies, tralkoxydim was readily absorbed & excreted within 24 & 48 hrs after dosing, respectively.
Based on the results of the hamster & rat metab studies, tralkoxydim was readily absorbed & excreted within 24 & 48 hrs after dosing, respectively. In hamsters, the metabolic profile in urine was similar for males & females; no unchanged tralkoxydim was detected & 2 major metabolites were identified: tralkoxydim acid & tralkoxydim acid oxazole. The metabolic profile in the urine of rats included 2 additional metabolites, tralkoxydim alcohol & tralkoxydim diol.
Technical material is 95% pure
tralkoxydim
Tralkoxydim Use and Manufacturing
By the action of 2, 4, 6-trimethylbenzaldehyde and acetone, the product is then reacted with diethyl malonate, and then hydrolyzed, cyclized, and decarboxylated to produce 3-hydroxy-5-(2', 4' , 6'-trimethylphenyl)-cyclohex-2-en-1-one. Then in the presence of sodium methoxide, it reacts with propionic acid anhydride and finally with ethoxylamine hydrochloride to prepare benzophenone.
Post-emergent herbicide.
USEPA/OPP Pesticide Code 121000; Trade Names: Achieve 40DG herbicide.|40% dry granular [Achieve 40 DG Herbicide]; 80% dry granular [Achieve 80 DG Herbicide]; Technical wet paste (81% manufacturing use product)|Emulsifiable concentrate; suspension concentrate|Water dispersible granules
Achieve 40 DG Herbicide formulation applied by ground and aerial application at 0.44 to 0.60 pounds per acre. Achieve 80 DG Herbicide formulation applied by ground and aerial application at 0.22 to 0.30 pounds per acre.
Agrochemicals -> Herbicides|Environmental transformation -> Pesticides (parent, predecessor)
Tralkoxydim has known environmental transformation products that include R158378, R163434, R173642, and R223068.
Computed Properties
Molecular Weight:329.4
XLogP3:4.1
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:5
Exact Mass:329.19909372
Monoisotopic Mass:329.19909372
Topological Polar Surface Area:58.9
Heavy Atom Count:24
Complexity:511
Undefined Atom Stereocenter Count:1
Undefined Bond Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
Latest News on Tralkoxydim
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