38260-54-7CCOc1cc(OP(=S)(OC)OC)nc(CC)n1FGIWFCGDPUIBEZ-UHFFFAOYSA-NEtrimfos is an organic thiophosphate.
38260-54-7DTXSID7041964CHEMBL1316772CHEBI:82124Acaricides, Insecticides
Active substance -> EU Pesticides database: Not approved
Pesticides -> Organophosphate Insecticides
Pesticide (Etrimfos) -> USDA PDB
Miscible with ethyl acetate and ether.
Solubility (23 °C): 40 mg/l water; completely miscible with acetone, chloroform, dimethyl sulfoxide, ethanol, hexane, methanol, xylene.
0.04 mg/mL at 23 °C
-3.35 °C
-3.35 °C
0.00008 [mmHg]
VP: 8.6 mPa (20 °C)
6.5x10-5 mm Hg at 20 °C
Colorless liquid; [Merck Index]
Liquid
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Warning
H302: Harmful if swallowed [Warning Acute toxicity, oral]
P264, P270, P273, P301+P317, P330, P391, and P501 (click each P-code to see the statement)
Danger
H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
P262, P264, P270, P273, P280, P301+P317, P302+P352, P316, P321, P330, P361+P364, P391, P405, and P501 (click each P-code to see the statement)
No evidence of mutagenicity in studies using hamsters and micro organisms; No reproductive or teratogenic effects observed in three generation, two litter generation study with rats; In a reproductive study with rabbits, minor reproductive toxicity (including decrease in number of implantations and increase in dead fetuses) was observed in the highest dose groups and 3 animals born with skeletal deformations; Caused no skin and mild eye irritation in rabbits; No significant adverse effects besides inhibition of cholinesterase activity was observed in long term feeding studies with rats; No evidence of delayed neuropathy in hens nor skin sensitization in guinea pigs; [INCHEM JMPR] The average of two baseline respective cholinesterase activity determinations three days apart, with no exposures to enzyme inhibiting pesticides for at least 30 days, is recommended for each worker prior to exposure to cholinesterase inhibitors because of large inter-individual differences in published baseline values. To be established at least once a year. Removal from workplace exposures is recommended until the cholinesterase activity returns to within 20% of baseline. [TLVs and BEIs]
Organophosphorus derivatives act by combining with and inactivating the enzyme acetylcholinesterase (AChE). ... The inactivation of cholinesterase by cholinesterase inhibitor pesticides allows the accumulation of large amounts of acetylcholine, with resultant widespread effects that may be ... separated into 4 categories: (1) Potentiation of postganglionic parasympathetic activity. ... (2) Persistent depolarization of skeletal muscle ... (3) Initial stimulation following depression of cells of central nervous system ... (4) Variable ganglionic stimulation or blockade ... /Cholinesterase inhibitor pesticides/
The main feature of the toxic mechanism of organophosphorus pesticides is inhibition of the esterase enzyme activity, in particular of cholinesterase, which plays an important physiological part. Organophosphorus pesticides can also indirectly interact with the biochemical receptors of acetylcholine. /Organophosphorus pesticides/
Non-systemic insecticide and acaricide with contact and stomach action. Cholinesterase inhibitor.
Plasma & tissue enzymes are responsible for hydrolysis /of organophosphorus compounds/ to the corresponding phosphoric & phosphonic acids. However, oxidative enzymes are also involved in the metabolism of some organophosphorus compounds. /Anticholinesterase agents/
The organophosphorus anticholinesterase agents are hydrolyzed in the body by a group of enzymes known as A-esterases or paroxonase. The enzymes are found in plasma and in the hepatic endoplasmic reticulum & can hydrolyze a large number of organophosphorus compounds ... by splitting the anhydride, P-F, P-CN, or ester bond. /Anticholinesterase agents/
These chemicals are detoxified by cytochrome p450-mediated monooxygenases in the liver, but some metabolites are more toxic than parent cmpd ... Metabolites usually are detected from 12 to 48 hr postexposure. /Organophosphate cmpd/
When etrimfos was administered to rats, most of the material was excreted in the urine. Five compounds, free and conjugated, were observed: 6-ethoxy-2-ethyl-4- hydroxypyrimidine; 2-ethyl-4,6-dihydroxypyrimidine; 6-ethoxy-4-hydroxy-2-(1- hydroxyethyl)pyrimidine; 6-ethoxy-4-hydroxy-2-(2-hydroxyethoxy)pyrimidine; and 2-ethyl-4-hydroxy-6-(2-hydroxyethoxy)pyrimidine. In urine of goats administered etrimfos, only the first three compounds above were observed.
For more Metabolism/Metabolites (Complete) data for ETRIMFOS (11 total), please visit the HSDB record page.
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불러오는 중…
Unstable when pure, but stable in dilute solution in non-polar solvents. For a 50 mg/l aqueous solution at 25 °C, 50% hydrolysis occurs in 0.4 days at pH 3, in 15.7 days at pH 6, and in 14 days at pH 9. High stability to light.
It is unstable in its pure form, but dilute solutions in nonpolar solvents and its formulations are stable (shelf life at 20 °C: about 2 yr).
Acute Tox. 4 (100%)
Acute toxicity - category 4
Acute Tox. 4 *
49 216 74; Organophosphorus pesticide, liquid, not otherwise specified (compounds and preparations) (insecticides, other than agricultural, NEC)
49 216 75; Organophosphorus pesticide, liquid, not otherwise specified (compounds and preparations) (agricultural insecticides, NEC, liquid)
49 105 44; Organophosphorus pesticide, liquid, not otherwise specified (compounds and preparations) (insecticides, other than agricultural, NEC)
49 105 45; Organophosphorus pesticide, liquid, not otherwise specified (compounds and preparations) (agricultural insecticides, NEC, liquid)
49 216 76; Organophosphorus pesticide, solid, not otherwise specified (compounds and preparations) (insecticides, other than agricultural, NEC)
49 216 77; Organophosphorus pesticide, solid, not otherwise specified (compounds and preparations) (agricultural insecticides, NEC, other than liquid)
No person may /transport,/ offer or accept a hazardous material for transportation in commerce unless that person is registered in conformance ... and the hazardous material is properly classed, described, packaged, marked, labeled, and in condition for shipment as required or authorized by ... /the hazardous materials regulations (49 CFR 171-177)./
The International Air Transport Association (IATA) Dangerous Goods Regulations are published by the IATA Dangerous Goods Board pursuant to IATA Resolutions 618 and 619 and constitute a manual of industry carrier regulations to be followed by all IATA Member airlines when transporting hazardous materials.
The International Maritime Dangerous Goods Code lays down basic principles for transporting hazardous chemicals. Detailed recommendations for individual substances and a number of recommendations for good practice are included in the classes dealing with such substances. A general index of technical names has also been compiled. This index should always be consulted when attempting to locate the appropriate procedures to be used when shipping any substance or article.
UN 3018; Organophosphorus pesticides, liquid, toxic, not otherwise specified
UN 3017; Organophosphorus pesticides, liquid, toxic, flammable, not otherwise specified, flashpoint between 23 °C and 61 °C
UN 2783; Organophosphorus pesticides, solid, toxic, not otherwise specified
UN 2784; Organophosphorus pesticides, liquid, flammable, toxic, not otherwise specified, flashpoint less than 23 °C
For more Shipping Name/ Number DOT/UN/NA/IMO (Complete) data for ETRIMFOS (6 total), please visit the HSDB record page.
Biological Exposure Indices (BEI) [ACGIH] - Acetylcholinesterase activity in red blood cells = 70% of individual's baseline; Butylcholinesterase activity in serum or plasma = 60% of individual's baseline; Sample at end of shift; [TLVs and BEIs]
LC50 Carp 13.6 mg/l/48 hr /Conditions of bioassay not specified/
LC50 Carp 13.3 mg/l/96 hr /Conditions of bioassay not specified/
LC50 Quail dietary 740 mg/kg/8 day /Conditions of bioassay not specified/
LC50 Guppy 5.5 mg/l/96 hr /Conditions of bioassay not specified/
LC50 Rainbow trout 24 ug/l/96 hr /Conditions of bioassay not specified/
TERRESTRIAL FATE: Etrimfos degrades readily in soil through hydrolytic and biochemical processes(1-2). It is rapidly metabolized in plants, animals and soil to 6-ethoxy-2-ethylpyrimidin-4-ol (EEHP), small amounts of 2-ethylpyrimidine-4,6-diol and other hydroxylated derivatives(1); traces of the P=O analog may also be formed(1-2). In soil, there is a rapid degradation to EEHP and further to volatile fragments, including CO2(1-2). The half-life in soil is typically 3-8 days(1). Estimated Koc values of 202 and 570 suggest that etrimfos has medium to low soil mobility(3-5).
AQUATIC FATE: Etrimfos is expected to degrade readily in water through hydrolysis and biodegradation. It hydrolyzes in water with a half-life of 14-16 days at pH6-pH9 and 25 °C(1-2). Although specific biodegradation data are not available, etrimfos is expected to biodegrade readily in natural water based upon data for similar phosphate esters(3). Following an accidental spill of etrimfos into the Rhine River, one computer model predicted that etrimfos would have a residence time of 23 days in the Rhine(3). Bioconcentration in aquatic organisms is not expected to be important; etrimfos is rapidly metabolized in plants and animals to 6-ethoxy-2-ethylpyrimidin-4-ol (EEHP), small amounts of 2-ethylpyrimidine-4,6-diol and other hydroxylated derivatives(1); traces of the P=O analog may also be formed(1-2). Volatilization from water has minor importance(3,SRC).
ATMOSPHERIC FATE: Based upon a vapor pressure of 6.45X10-5 mm Hg at 20 °C(1), etrimfos can exist in both the vapor and particulate-phases in the ambient atmosphere, although the vapor-phase can be expected to dominate(2,SRC). It will degrade rapidly in the vapor-phase by reaction with photochemically produced hydroxyl radicals with an estimated half-life of 4.8 hr(3,SRC). Particulate-phase etrimfos and aerosols released to air during spray applications of etrimfos insecticide will be removed from air physically by dry and wet deposition(SRC).
In soil, 50% loss of etrimfos occurs in ca 3-8 days. The principal degradation products are 6-ethoxy-2-ethylpyrimidin-4-ol, small amounts of 2-ethylpyrimidine-4,6-diol and other hydroxylated derivatives, and carbon dioxide.
Analysis of 327 wheat samples collected from United Kingdom flour mills during 1987 and 1988 found etrimfos in only two samples (max concn of 0.3 mg/kg) at a detection limit of 0.1 mg/kg(1); etrimfos was not detected in 142 samples of wheat imported into the United Kingdom(1).
In plants, etrimfos undergoes rapid metabolism to 6-ethoxy-2-ethylpyrimidin-4- ol, and small amounts of 2-ethylpyrimidine-4,6-diol and other hydroxylated derivatives.
Workers handling & applying pesticides must undergo an annual medical examination at the beginning of each agricultural season. Contraindications for work with /organophosphorus pesticides/ are organic diseases of the central nervous system, mental disorders & epilepsy, pronounced endocrine & vegetative disorders, pulmonary tuberculosis, bronchial asthma, chronic respiratory diseases, cardiovascular diseases & circulatory disorders, gastrointestinal diseases (peptic ulcer), gastroenterocolitis, diseases of liver & kidneys, eye diseases (chronic conjunctivitis & keratitis). The blood cholinesterase activity must be determined before work starts. In the event of prolonged work periods, this activity should be determined at intervals of 3-4 days. Persons exhibiting a fall in cholinesterase activity of 25% or more must be transferred to other work where they are not exposed to organophosphorus pesticides until this activity is completely restored. Persons with initial signs of indisposition should cease work with pesticides. /Organophosphorus pesticides/
A final diagnosis of mild to moderate acute organophosphate pesticide poisoning is rarely justified unless all of the following five conditions are present: 1. A definite history of exposure to an organophosphate pesticide. 2. A latent interval of not more than a few hours between that last exposure and the onset of illness. 3. A clinical picture in which most or all of the following signs or symptoms are present: headache, blurred vision, weakness, tightness in chest, and constricted pupils. 4. Reduction of plasma and RBC cholinesterase activity to a level substantially below 50% of baseline values. Because of the wide normal range of RBC cholinesterase in the population, symptoms may be present with reported "normal" levels. 5. An acute illness that is not substantially longer than 48 hours. The classic presentation for acute organophosphate toxicity includes history, evidence of exposure to organophosphate (garlic odor), signs/symptoms of cholinergic excess, improvement with atropine or pralidoxime, and inhibition of cholinesterase in blood. /Organophosphate pesticide poisoning/
Based upon a reported water solubility of 40 mg/L at 23 °C(1), the Koc for etrimfos can be estimated to be about 570 from a regression-derived equation(2,SRC). Using a structure estimation method based on molecular connectivity indexes, the Koc for etrimfos can be estimated to be 202(3,SRC). According to a suggested classification scheme(4), these estimated Koc values suggest that etrimfos has medium to low mobility in soil(SRC). Following an accidental spill of etrimfos into the Rhine River in Switzerland (estimated discharge of 290-1800 kg), monitoring suggested that etrimfos did not strongly adsorb in sediment and particles in the water(4).
All the organophosphorus insecticides have a cumulative effect by progressive inhibition of cholinesterase ... /Organophosphorus insecticides/
The symptoms of chronic poisoning due to organophosphorus pesticides include headache, weakness, feeling of heaviness in head, decline of memory, quick onset of fatigue, disturbed sleep, loss of appetite, & loss of orientation. Psychic disorders, nystagmus, trembling of the hands & other nervous system disorders can be observed in certain cases. Sometimes neuritis, paresis & paralysis develop. /Organophosphorus pesticides/
Organophosphorus cmpd can produce dermal irritation but most are weak sensitizers. /Organophosphate cmpd/
Toxic effects may include anorexia, abdominal cramps, nausea, vomiting, diarrhea, incontinence, eye changes, weakness, dyspnea, bronchospasm, lacrimation, increased salivation & sweating, bradycardia, hypotension or hypertension due to asphyxia, cyanosis, & muscular twitching of the eyelids, tongue, face, & neck, possibly progressing to convulsions. Central nervous system symptoms include restlessness, anxiety, dizziness, drowsiness, tremor, ataxia, depression, confusion, & coma. Death may occur from depression of the respiratory or cardiovascular system. Neuropathy appears to be a rare problem with the organophosphorus insecticides now in use. /Organophosphorus insecticides/
For more Human Toxicity Excerpts (Complete) data for ETRIMFOS (9 total), please visit the HSDB record page.
Based upon a reported water solubility of 40 mg/L(1), the BCF for etrimfos can be estimated to be 77 from a recommended regression-derived equation(2,SRC). This BCF value suggests that bioconcentration in aquatic organisms is not important(SRC).
Based upon a water solubility of 40 mg/L and a vapor pressure of 6.45X10-5 mm Hg at 20 °C(1), the Henry's Law constant for etrimfos can be estimated to be 6.2X10-7 atm-cu m/mole(SRC). This value of Henry's Law constant suggests that a compound volatilizes slowly from water(2). Based on this Henry's Law constant, the volatilization half-life from a model river (1 m deep flowing 1 m/sec with a wind velocity of 3 m/sec) can be estimated to be about 101 days(2,SRC). Volatilization half-life from an model environmental pond (2 meters deep) can be estimated to exceed 4 yrs(3,SRC).
Most organophosphate compounds are ... absorbed from skin, conjunctiva, gastrointestinal tract, & lung. /Organophosphate compounds/
The rate of dermal absorption /of organophosphorus pesticides/ may be ... influenced by the solvent used. /Organophosphorus pesticides/
... The organophosphorus insecticides are, in contrast to the chlorinated insecticides, rapidly metabolized & excreted and are not appreciably stored in body tissues. /Organophosphorus insecticides/
Many of the organophosphorus insecticides are excreted in the milk ... . /Organophosphorus insecticides/
For more Absorption, Distribution and Excretion (Complete) data for ETRIMFOS (8 total), please visit the HSDB record page.
Used as broad range non-systemic insecticide for fruits, vegetables, maize, ornamentals, tobacco, rice, and other crops; [HSDB]
Farming (Pesticides) [Category: Industry]
Insecticide
Control of Lepidoptera, Coleoptera, Diptera, and some Hemiptera on fruit trees (including citrus), olives, potatoes, vegetables, maize, lucerne, ornamentals, tobacco, and rice; and control of Lepidoptera, Coleoptera, mites, and lice in stored products.
All purpose insecticide for house gardens and handling equipment. Controls scales in fruit trees, citrus and olives, grape berry moths in grapes, European corn borer, Colorado potato beetle, lepidopterous pests of tobacco, prebloom and early postbloom pest complexes on fruit trees: rice stemborers, beetles, midges and bugs, and alfalfa weevils. Granular for Pyralidae in paddy rice.
Etrimfos's use as broad-range non-systemic insecticide(1-2).
Emulsifiable concentrate; granules; ultra-low volume liquid; dustable powder.
Ekamet, emulsifiable concentrate (500 g/kg), granules (50 g/kg), dustable powder (10 or 20 g/kg), oil spray (50 g/kg); Ekamet ultra-low volume (400 g/l); Satisfar (520 g/l); Satisfar DP-2, dsut (20 g/kg); Satisfar LS 3, Satisfar LS 5 (30 or 50 g/l).
개요Etrimfos 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.
용도Etrimfos 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.