326-12-5COP(=O)(OC)O/C(C)=C/C(=O)OC(C)c1ccccc1XXXSILNSXNPGKG-ZHACJKMWSA-NCrotoxyphos is a carboxylic ester. It is functionally related to a benzyl alcohol.
326-12-5、7700-17-6DTXSID6037514CHEMBL2104169CHEBI:82110Pesticides -> Organophosphate Insecticides
Pesticide (Crotoxyphos) -> USDA PDB
1.19 @ 25 °C
DENSITY: 1.2 @ 15 °C/15 °C
LIGHT STRAW-COLORED LIQ
Clear liquid
0.1%; SLIGHTLY SOL IN KEROSENE, SATURATED HYDROCARBONS; SOL IN ACETONE, CHLOROFORM, ETHANOL, HIGHLY CHLORINATED HYDROCARBONS
0.1% in water at room temperature
SOL IN PROPAN-2-OL, XYLENE
Slightly corrosive to copper, lead, mild steel, tin and zinc, but will not attack fiberglass, reinforced polyester, rigid PVC, or the usual lacquers used for lining drums. Incompatible with most mineral carriers, except synthetic silicas such as 'Colloidal Silica K320' and 'Hisil 233'.
0.000014 [mmHg]
1.4X10-5 mm Hg @ 20 °C
안전 정보는 참고용이며, 공급업체의 물질안전보건자료(SDS), 관련 법규 및 전문가 평가를 대체하지 않습니다.
Danger
H301: Toxic if swallowed [Danger Acute toxicity, oral]
P262, P264, P270, P273, P280, P301+P316, P302+P352, P316, P321, P330, P361+P364, P391, P405, and P501 (click each P-code to see the statement)
Danger
H301 (97.6%): Toxic if swallowed [Danger Acute toxicity, oral]
P262, P264, P270, P273, P280, P301+P316, P302+P352, P316, P321, P330, P361+P364, P391, P405, and P501 (click each P-code to see the statement)
A cholinesterase inhibitor; [Merck Index] No adverse effects to growth or histopathological changes were observed in 90 day feeding study with rats (males at 900 mg/kg diet and females 300 mg/kg diet); Cholinesterase inhibitor; [HSDB] 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]
As the federal pesticide law FIFRA directs, EPA is conducting a comprehensive review of older pesticides to consider their health and environmental effects and make decisions about their future use. Under this pesticide reregistration program, EPA examines health and safety data for pesticide active ingredients initially registered before November 1, 1984, and determines whether they are eligible for reregistration. In addition, all pesticides must meet the new safety standard of the Food Quality Protection Act of 1996. Pesticides for which EPA had not issued Registration Standards prior to the effective date of FIFRA, as amended in 1988, were divided into three lists based upon their potential for human exposure and other factors, with List B containing pesticides of greater concern and List D pesticides of less concern. Dimethylphosphate ester of alpha-methylbenzyl-3-hydroxy-cis-crotonate is found on List B. Case No: 2120; Pesticide type: insecticide; Case Status: No products containing the pesticide are actively registered ... The case /is characterized/ as "cancelled." Under FIFRA, pesticide producers may voluntarily cancel their registered products. EPA also may cancel pesticide registrations if registrants fail to pay required fees or make/meet certain reregistration commitments, or if EPA reaches findings of unreasonable adverse effects.; Active ingredient (AI): Dimethylphosphate ester of alpha-methylbenzyl-3-hydroxy-cis-crotonate; AI Status: Registrants of the pesticide have not made or honored a commitment to seek reregistration, conduct the necessary studies, or pay the requisite fees, or they have asked EPA to cancel their product registrations. Unless some other interested party supports them, products containing the pesticide will be cancelled. The active ingredient is no longer contained in any registered pesticide products ... "cancelled."
STUDIES WITH (32)P-LABELED CIODRIN...LACTATING EWES AND LACTATING GOATS SHOWED HYDROLYTIC FISSION TO AFFORD CORRESPONDING MONOMETHYLPHOSPHATE AND DIMETHYLPHOSPHATE.
IN LACTATING EWE AFTER ORAL ADMIN, (32)P-CIODRIN IS RAPIDLY METABOLIZED... PRINCIPAL METABOLITE WAS DIMETHYL PHOSPHORIC ACID CONSISTING OF 60-90% OF TOTAL RADIOACTIVITY IN URINE. ANOTHER IMPORTANT METABOLITE WAS 3-(DIMETHOXYPHOSPHINYLOXY)CROTONIC ACID WHICH APPEARED AS 11% OF METABOLITES AFTER 3 HR, DECR TO 3% AFTER 6 HR.
STUDIES WITH (32)P-LABELED CIODRIN...IN LACTATING EWES AND...GOATS SHOWED HYDROLYTIC FISSION TO...THE CORRESPONDING MONOMETHYLPHOSPHATE AND DIMETHYLPHOSPHATE. IN BOTH SPECIES, MAJOR ELIMINATIVE ROUTE WAS URINARY, AND VERY SMALL AMT OF UNCHANGED /CIODRIN/ IN MILK CONSISTED ONLY OF BETA-ISOMER.
STUDY OF ABSORPTION, ELIMINATION & METABOLISM OF ORALLY ADMIN (32)P LABELED CIODRIN IN LACTATING EWE INDICATED MODERATE ABSORPTION & RAPID ELIMINATION. DIMETHYL PHOSPHORIC ACID ACCOUNTED FOR 61-90% OF RADIOACTIVITY IN URINE. ... SIMILAR RESULTS WERE OBTAINED...WITH A LACTATING GOAT.
IN LACTATING EWE AFTER ORAL ADMIN, (32)P-CIODRIN IS RAPIDLY METABOLIZED & ELIMINATED IN URINE, 79% OF ELIMINATED DOSE BEING ELIMINATED IN TWO DAYS.
Used as insecticide to protect livestock (external use); [Merck Index]
Cancelled--no longer registered as a pesticide for use in the US; [HSDB]
Farming (Pesticides) [Category: Industry]
The active ingredient is no longer contained in any registered pesticide products ... "cancelled."
INSECTICIDE FOR EXTERNAL USE ON LIVESTOCK
Recommended for the control of flies, mites and ticks on cattle and pigs.
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INDEX OF REFRACTION: 1.4988 @ 25 °C/D
INDEX OF REFRACTION: 1.5505 @ 25 °C/D
IN AQ SOLN AT 38 °C, 50% IS HYDROLYZED IN 87 HR AT PH 1, 35 HR AT PH 9. ...WILL NOT ATTACK FIBERGLASS, REINFORCED POLYESTER, RIGID PVC, OR THE USUAL LACQUERS USED FOR LINING DRUMS.
...STABLE IN PRESENCE OF HYDROCARBON SOLVENTS; HYDROLYZED IN PRESENCE OF WATER...
Yellowish liquid. Soluble in acetone, alcohol, chlorinated hydrocarbons; slightly soluble in saturated hydrocarbons.
Crotoxyphos
Marine pollutant
Acute Tox. 3 (97.6%)
Acute toxicity - category 3
Acute toxicity (Oral) - Category 2
Acute Tox. 3 *
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]
SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.
LD50 MALLARD ORAL 790 MG/KG (95% CONFIDENCE LIMIT 411-1520 MG/KG), 3-4 MO OLD MALES /TECHNICAL, 85%/
LC50 Gammarus lacustris 49.0 ug/L/24 hr @ 15 °C (95% confidence limit 36.0-67.0 ug/L), mature. Static bioassay without aeration, pH 7.2-7.5, water hardness 40-50 mg/l as calcium carbonate and alkalinity of 30-35 mg/l. /Technical, 80%/
LC50 Pteronarcys 2.2 ug/L/72 hr @ 15 °C, second year class. Static bioassay without aeration, pH 7.2-7.5, water hardness 40-50 mg/l as calcium carbonate and alkalinity of 30-35 mg/l. /Technical, 80%/
LC50 Salmo clarki (cutthroat trout) 51.0 ug/L/96 hr @ 12 °C (95% confidence limit 28.0-91.0 ug/L), wt 1.0 g. Static bioassay without aeration, pH 7.2-7.5, water hardness 40-50 mg/l as calcium carbonate and alkalinity of 30-35 mg/l. /Technical, 80%/
For more Ecotoxicity Values (Complete) data for CIODRIN (10 total), please visit the HSDB record page.
DEGRADATION OF CIODRIN VARIED BETWEEN SOILS. HALF-LIFE VALUE VARIED FROM 2 HR IN A POYGAN SILTY CLAY LOAM TO 71 HR IN AN ELLA LOAMY SAND. IN AQUEOUS SOIL-FREE SYSTEMS HALF-LIFE VALUES FOR CIODRIN DEGRADATION WERE 180, 410, AND 540 HR AT PH 9, 6, AND 2, RESPECTIVELY.
AN ENZYME WHICH CATALYZED THE HYDROLYSIS OF CROTOXYPHOS WAS ISOLATED FROM NONSTERILE & RADIATION STERILE CHEHALIS CLAY LOAM. IT WAS HYDROLYZED TO DIMETHYL PHOSPHATE & ALPHA-METHYLBENZYL 3-HYDROXY CROTONATE IN 16 HR @ 37 °C.
TERRESTRIAL FATE: If released on land, Ciodrin will adsorb moderately to the soil and biodegrade in about a day(2). In experiments performed on the biodegradion of Ciodrin in three soil-water solutions, 14C-Ciodrin concentrations showed a very rapid initial decline resulting from adsorption and then continued to decline at a slower rate due to biodegradation(1). As degradation proceeded, degradation products were released into the solution and all the 14C was found in solution at the end of the experiment. In each soil system, Ciodrin degradation followed first-order kinetics and was related to the extent of initial adsorption. At pH 6.0, the degradation rate in the soil system is two orders of magnitude greater than in aqueous solution. The half-lives of Ciodrin in the soil-water systems are: Poygan silty clay loam (2.2% OC, pH 7.2), 2.00 hr (nonsterile) and 3.75 hr (sterile); Kewanunee Clay (5.8% OC, pH 6.4), 5.50 hr (nonsterile) and 6.00 hr (sterile); and Ella loamy sand (0.93% OC, pH 3.8), 71.0 hr (nonsterile) and 77.0 hr (sterile)(1). The decrease in rate in the electron-beam-sterilized soil was due to decreased Ciodrin adsorption due to the treatment, rather than from retardation of microbial degradation(1). The degradation involves an initial hydrolysis of the ester linkage leading to 3(methoxyphosphinyloxy)crotonic acid(1). The final products are dimethylphosphoric acid, cis-hydroxycrotonic acid, and 1-phenylethanol which are all water soluble(1). In laboratory studies in Chehalis clay loam, 87% of the applied ciodrin degraded in 1 day(2). The enzyme responsible for the degradation exhibits maximum activity at pH 8 and is heat labile(3).
AQUATIC FATE: If released in water, ciodrin will be lost due to hydrolysis. The hydrolysis half-lives are 540, 410 and 180 hr at pH 2.0, 6.0, and 9.0, respectively(1). Ciodrin will also adsorb moderately to sediment and particulate matter in the soil column and hydrolyze by a microbially mediated process approximately 2 orders of magnitude faster than in water(1). Ciodrin would not be expected to volatilize from water or bioconcentrate in fish(SRC).
ATMOSPHERIC FATE: If released into the atmosphere during spraying, ciodrin-containing aerosols will be removed by gravitational settling. Ciodrin has a vapor pressure of 1.4X10-5 mm Hg at 25 °C(2). In the atmosphere, Ciodrin will exist primarily as the vapor(3). Vapor-phase Ciodrin will react with photochemically-produced hydroxyl radicals resulting in an estimated atmospheric half-life of 4.2 hr(1).
The mean soil water distribution coefficient of Ciodrin in 3 soils, Poygan silty clay loam (2.2% OC, pH 7.2), Kewanunee Clay (5.8% OC, pH 6.4), and Ella loamy sand (0.93% OC, pH 3.8) was 6.09(1,2). The mean Koc value for these soils was 173(1). According to a suggested classification scheme(3), a Koc value of 173 suggests moderate mobility in soil(SRC).
A CHOLINESTERASE INHIBITOR.
Symptomatology: 1. Nausea...vomiting, abdominal cramps, diarrhea, excessive salivation... 2. Headache, giddiness, vertigo & weakness. 3. Rhinorrhea & sensation of tightness in chest are common in inhalation exposure. 4. Blurring or dimness of vision, miosis... Tearing, ciliary muscle spasm, loss of accommodation & ocular pain... Mydriasis...sometimes seen...probably due to sympatho-adrenal discharge. 5. Bradycardia or tachycardia. Varying degrees of AV heart block are described, as well as atrial arrhythmias. 6. Loss of muscle coordination, slurring of speech, fasciculations & twitching of muscles (particularly of tongue & eyelids, & generalized profound weakness. 7. Mental confusion, disorientation & drowsiness. /Parathion/
Symptomatology: 8. Difficulty in breathing, excessive secretion of saliva & of resp tract mucus, oronasal frothing, cyanosis, pulmonary rales & rhonchi & hypertension (presumably due to asphyxia). 9. Random jerky movements, incontinence, convulsions, & coma. 10. Death primarily due to resp arrest arising from failure of resp center, paralysis of resp muscles, intense bronchoconstriction or all three. /Parathion/
Ciodrin was released to the environment as a result of its use (by spraying) as an insecticide for the control of external insect pests on livestock and it was recommended for the control of flies, mites and ticks on cattle and pigs(1,2). However, its registration has been cancelled(3) and therfore it should no longer be released. It may also have been released during its production, transport, formulation, and disposal(SRC).
In experiments performed on the biodegradion of Ciodrin in three soil-water solutions, 14C-Ciodrin concentrations showed a very rapid initial decline resulting from adsorption and then continued to decline at a slower rate due to biodegradation(1). As degradation proceeded, degradation products were released into the solution and all the 14C was found in solution at the end of the experiment. In each soil system, Ciodrin degradation followed first-order kinetics and was related to the extent of initial adsorption. At pH 6.0, the degradation rate in the soil system is two orders of magnitude greater than in aqueous solution. The half-lives of Ciodrin in the soil-water systems are: Poygan silty clay loam (2.2% OC, pH 7.2), 2.00 hr (nonsterile) and 3.75 hr (sterile); Kewanunee Clay (5.8% OC, pH 6.4), 5.50 hr (nonsterile) and 6.00 hr (sterile); and Ella loamy sand (0.93% OC, pH 3.8), 71.0 hr (nonsterile) and 77.0 hr (sterile)(1). The decrease in rate in the electron-beam-sterilized soil was due to decreased Ciodrin adsorption due to the treatment, rather than from retardation of microbial degradation(1). The degradation involves an initial hydrolysis of the ester linkage leading to 3(methoxyphosphinyloxy)crotonic acid(1). The final products are dimethylphosphoric acid, cis-hydroxycrotonic acid, and 1-phenylethanol which are all water soluble(1). In laboratory studies in Chehalis clay loam, 87% of the applied ciodrin degraded in 1 day(2). The enzyme responsible for the degradation exhibits maximum activity at pH 8 and is heat labile(3).
As the federal pesticide law FIFRA directs, EPA is conducting a comprehensive review of older pesticides to consider their health and environmental effects and make decisions about their future use. Under this pesticide reregistration program, EPA examines health and safety data for pesticide active ingredients initially registered before November 1, 1984, and determines whether they are eligible for reregistration. In addition, all pesticides must meet the new safety standard of the Food Quality Protection Act of 1996. Pesticides for which EPA had not issued Registration Standards prior to the effective date of FIFRA, as amended in 1988, were divided into three lists based upon their potential for human exposure and other factors, with List B containing pesticides of greater concern and List D pesticides of less concern. Dimethylphosphate ester of alpha-methylbenzyl-3-hydroxy-cis-crotonate is found on List B. Case No: 2120; Pesticide type: insecticide; Case Status: No products containing the pesticide are actively registered ... The case /is characterized/ as "cancelled." Under FIFRA, pesticide producers may voluntarily cancel their registered products. EPA also may cancel pesticide registrations if registrants fail to pay required fees or make/meet certain reregistration commitments, or if EPA reaches findings of unreasonable adverse effects.; Active ingredient (AI): Dimethylphosphate ester of alpha-methylbenzyl-3-hydroxy-cis-crotonate; AI Status: Registrants of the pesticide have not made or honored a commitment to seek reregistration, conduct the necessary studies, or pay the requisite fees, or they have asked EPA to cancel their product registrations. Unless some other interested party supports them, products containing the pesticide will be cancelled. The active ingredient is no longer contained in any registered pesticide products ... "cancelled."
EMULSIFIABLE CONCENTRATES 2 & 4 LB/GAL; DILUTE OIL SOLN 2% WT/VOL; DUSTS 3% & 20% WT.
Ciovap: Ciodrin (crotoxyphos) + Vapona (dichlorvos)
Emulsifiable concentrate 240 g active ingredient/L /Ciodrin/
BRITISH PATENT 855,238 (1960 TO BATAAFSE PETROLEUM MAATSCHAPPIJ NV); WHETSTONE, STILES, US PATENT 2,982,686 (1961 TO SHELL).
WITH THE EXCEPTION OF VAPONA, WITH WHICH IT IS COMPATIBLE, CIODRIN IS NOT NORMALLY USED IN MIXTURES WITH OTHER BIOCIDES.
VET: DO NOT RESPRAY MORE OFTEN THAN ONCE WEEKLY. BRAHMAN CATTLE ARE PARTICULARLY SUSCEPTIBLE TO TOXICITY FROM IT (EVEN AT 0.1% CONCN). DO NOT TREAT CALVES UNDER 6 MONTHS OF AGE. NO WITHDRAWAL PERIOD BEFORE MILKING OR SLAUGHTERING CATTLE AFTER AQ SPRAYS OR DUSTS.
TECHNICAL CIODRIN CONSISTS OF 2 ISOMERS, ALPHA & BETA, WITH ALPHA PREDOMINATING OVER BETA. CONFIGURATIONS FOR ISOMERS HAVE NOT BEEN ASSIGNED.
For more General Manufacturing Information (Complete) data for CIODRIN (8 total), please visit the HSDB record page.
용도Crotoxyphos is an insecticide for external use on livestock.