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| | ETRIMFOS Basic information |
| Product Name: | ETRIMFOS | | Synonyms: | SATISFAR;O-(6-ETHOXY-2-ETHYL-4-PYRIMIDINYL)-O,O-DIMETHYLTHIOPHOSPHATE;Dimethyl-O-(2-ethyl-4-ethoxy-pyrimidinyl-6)-thionophosphate;Ekamet G;Ekamet ulv;ekametg;ekametulv;ENT 29126 | | CAS: | 38260-54-7 | | MF: | C10H17N2O4PS | | MW: | 292.29 | | EINECS: | 253-855-9 | | Product Categories: | | | Mol File: | 38260-54-7.mol |  |
| | ETRIMFOS Chemical Properties |
| Melting point | -3.35℃ | | Boiling point | approximate 77℃ | | density | 1.195 g/cm3 (20℃) | | vapor pressure | 6.5 x 10-3 Pa (24 °C) | | refractive index | nD20 1.5068 | | Fp | >100 °C | | storage temp. | APPROX 4°C | | solubility | Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly) | | pka | -0.67±0.32(Predicted) | | form | liquid | | Water Solubility | 40 mg l-1 (23-24 °C) | | color | Colourless | | Merck | 13,3923 | | BRN | 7136389 | | Henry's Law Constant | 1.6×101 mol/(m3Pa) at 25℃, HSDB (2015) | | InChI | 1S/C10H17N2O4PS/c1-5-8-11-9(15-6-2)7-10(12-8)16-17(18,13-3)14-4/h7H,5-6H2,1-4H3 | | InChIKey | FGIWFCGDPUIBEZ-UHFFFAOYSA-N | | SMILES | CCOc1cc(OP(=S)(OC)OC)nc(CC)n1 | | CAS DataBase Reference | 38260-54-7 | | EPA Substance Registry System | Etrimfos (38260-54-7) |
| Hazard Codes | Xn,N | | Risk Statements | 22-50/53 | | Safety Statements | 60-61 | | RIDADR | UN3082 9/PG 3 | | WGK Germany | 3 | | RTECS | TF8350000 | | Storage Class | 11 - Combustible Solids | | Hazard Classifications | Acute Tox. 4 Dermal
Aquatic Acute 1 | | Hazardous Substances Data | 38260-54-7(Hazardous Substances Data) | | Toxicity | LD50 in male rats, mice (mg/kg): 1800, 437 orally; LC50 in carp (mg/l): 13.6 (48 hr); 13.3 (96 hr) (Knutti) |
| | ETRIMFOS Usage And Synthesis |
| Description | Etrimfos is a colorless liquid, mp 3.35 C, vp 6.5 mPa
(20 C). Solubility in water is 40 mg/L (23–24 C). It is
miscible with most organic solvents. Log Kow > 3.3. Neat
etrimfos is unstable and degrades ca. 40% in 28 d at
50 C, but the dilute solutions in nonpolar solvents and its
formulations are stable (about 5% loss in 1 y at ca. 20 C).
It is hydrolyzed in aqueous media; DT50 (25 C) at pH 3, 6,
and 9 are 0.4, 16, and 14 d, respectively. | | Chemical Properties | Pure product is colorless oily liquid, m.p. -3.4℃, relative density 1.195 (20℃), refractive index n20D1.5068, can be mutually soluble with acetone, chloroform, methanol, ethanol, hexanol, dimethyl sulfoxide, xylene, solubility in water 10g/L, 25℃ hydrolysis half-life of 0.4d (pH=3), 16d (pH=6), 14d (pH=9). Ethylpyrimidine sulfide is unstable in pure form, but is stable in dilute solutions in nonpolar solvents for which suitable stabilizers have been reported. | | Uses | Satisfar is a pesticide sprayed on plants and vegetables as insecticide to fend off pests. | | Uses | Agricultural insecticide. | | Uses | Etrimfos is used to control chewing insects in top fruit, vines,
olives and a number of other crops. It is also used to control stem borers in
rice and insect and acarid pests of stored products. | | Definition | ChEBI: Etrimfos is an organic thiophosphate. | | Hazard | Toxic. | | Metabolic pathway | Etrimfos is principally degraded in soil and plants via dearylation of
etrimfos itself or by hydrolysis of etrimfos oxon to the pyrimidinol
(6-ethoxy-4-hydroxy-2-ethylpyrimidine), further metabolism of which
involves de-ethylation to a dihydroxypyrimidine (2-ethyl-4,6-dihydroxypyrimidine).
In mammals both hydrolysis and demethylation to desmethyl
etrimfos are involved in detoxification. Additionally, the ethyl and
ethoxy groups of the pyrimidinol hydrolysis product may be hydroxylated
and conjugated. Etrimfos oxon is metabolically highly unstable and
is often not detected. | | Degradation | Etrimfos is unstable when pure but dilute solutions in non-polar solvents
and formulations are stable. Half-lives in water at pH 3,6 and 9 were 0.4,
16 and 14 days, respectively. Etrimfos is stable to light (PM). | | Toxicity evaluation | The acute oral LD50 for rats is 1,600–1,800 mg/kg.
Inhalation LC50 (1 h) for rats is >200 mg/L air. NOEL
(2 yr) for rats is 6 mg/kg diet (0.3 mg/kg/d). ADI is
3 μg/kg b.w. The principal degradation pathway in
mammals, plants, and soils is pyrimidinyl ester bond
cleavage: the major metabolites are 6-ethoxy-4-hydroxy-
2-ethylpyrimidine and its further transformed products.
Degradation in mammals involves demethylation to
desmethyl etrimfos. The DT50 in soils at pH 6.8 was
3–10 d. |
| | ETRIMFOS Preparation Products And Raw materials |
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