950-10-7CCOP(=O)(/N=C1\SCC(C)S1)OCCLTQSAUHRSCMPLD-CMDGGOBGSA-NMephosfolan is a yellow to amber liquid. Works as an insecticide and acaricide. Not registered as a pesticide in the U.S. (EPA, 1998)
950-10-7CHEMBL2272786CHEBI:82141Insecticides
Active substance -> EU Pesticides database: Not approved
Pesticides -> Organophosphate Insecticides
Pesticide (Mephosfolan) -> USDA PDB
1.539 @ 26 °C
1.539 @ 26°C
Colorless liquid
Yellow to amber liquid.
Soluble in acetone, xylene, benzene, ethanol and toluene, moderately soluble in water.
Solubility in water at 25 °C: 57 g/kg.
248 °F at 0.001 mmHg (EPA, 1998)
120 °C at 1X10-3 mmHg
410 °C @760 [mm Hg]
0.0000318 [mmHg]
0.0000000001 [mm Hg] @25 °C
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Danger
H300: Fatal 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
H300 (100%): Fatal 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)
2002/2076
The New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.)
A highly toxic cholinesterase inhibitor; [CAMEO] 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]
Undergoes oxidation at the methyl group to form primary alcohol in addition to the formation of the thiocyanate ion in plants.
In the urine of rats dosed with cytrolane, TLC and MS indicated that the methyl moiety was attacked to produce carboxylic ions. Hydrolysis of the P-N bond was followed by ring opening and release of thiocyanate. The latter was the main tissue metabolite.
(14)C Cytrolane ..., labeled at the imino carbon, was applied to leaves of cotton plants. After 42 days, about 60% of the label was recovered as unchanged cytrolane. A minor metabolite ... and a major metabolite ... were isolated as glucosides. Identification of the aglycones was made after hydrolysis of the glucosidic moiety with beta-glucosidase. Another minor metabolite was identified as thiocyanate. Other observed metabolites were not identified. The hydroxymethyl and its glucoside were also observed in other studies with cotton.
When (14)C labeled cytrolane was applied to rice, about 91% of the residue was unchanged material. The remainder of the radioactivity was composed of about 17 metabolites. Unextractable radioactivity was believed to be in the form of (14)C-labeled cellulose, lignin and starch. Fish kept in the rice paddy metabolized cytrolane to thiocyanate and many other metabolites.
Used as contact and stomach insecticide and acaricide for cotton, fruits, vegetables, maize, and other crops; [HSDB]
Not registered in the US for use as pesticide; [CAMEO]
Farming (Pesticides) [Category: Industry]
Has shown significant activity against certain of the more important borer insects such as European corn borer, sugar cane borer and fall armyworm.
Insecticide, acaricide
It is a contact and stomach inseticide, and is used for the control of aphids, bollworms, mites, stem borers and whiteflies on such major crops as cotton, maize, field crops, fruit and vegetables.
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Mephosfolan is a yellow to amber liquid. Works as an insecticide and acaricide. Not registered as a pesticide in the U.S. (EPA, 1998)
Colorless or yellow to amber liquid; [HSDB]
It is stable in water under neutral, slightly acid or basic conditions. Photodegradation in an aqueous environment.
Hydrolysed at pH < 2 and at pH > 9 /technical/
... Hydrolyzed by acid or alkali.
When heated to decomposition, MEPHOSFOLAN emits very toxic fumes of nitrogen oxides, phosphorus oxides and sulfur oxides. Stable at neutral pH. Hydrolyzed by acid or alkali. [EPA, 1998]. Organophosphates, such as MEPHOSFOLAN, are susceptible to formation of highly toxic and flammable phosphine gas in the presence of strong reducing agents such as hydrides. Partial oxidation by oxidizing agents may result in the release of toxic phosphorus oxides.
Mephosfolan
Marine pollutant
Releases of CERCLA hazardous substances are subject to the release reporting requirement of CERCLA section 103, codified at 40 CFR part 302, in addition to the requirements of 40 CFR part 355. Mephosfolan is an extremely hazardous substance (EHS) subject to reporting requirements when stored in amounts in excess of its threshold planning quantity (TPQ) of 500 lbs.
Acute Tox. 2 (100%)
Acute toxicity (dermal) - category 1
Acute Tox. 1
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.
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]
(Non-Specific -- Organic Phosphate, Liquid) Use water spray to knock down vapors. Build dikes to contain material as necessary. Avoid breathing vapors. Keep upwind. Avoid bodily contact with the material. Downwind evacuation should be considered. (EPA, 1998)
0.82 [mg/m3]
9 [mg/m3]
54 [mg/m3]
For emergency situations, wear a positive pressure, pressure-demand, full facepiece self-contained breathing apparatus (SCBA) or pressure- demand supplied air respirator with escape SCBA and a fully-encapsulating, chemical resistant suit. (EPA, 1998)
LC50 Salmo spp (Trout) 2.12 mg/l/96 hr /Conditions of bioassay not specified/
LC50 Cyprinus carpio (Carp) 54.5 mg/l/96 hr /Conditions of bioassay not specified/
LD50 Coturnix coturnix japonica (Japanese quail) oral 12.8 mg/kg
TC50 Apis mellifera (Honeybee) topical application 0.0035 mg/bee
The persistence of mephosfolan and phorate in soils treated previously with these insecticides and in previously untreated soils was studied in lab incubations. Accelerated loss of mephosfolan was induced by a single pretreatment. More than 95% of freshly applied mephosfolan degraded in previously treated hop yard soils after 8 wk at 15 °Compared with 23-35% in the corresponding previously untreated soils. In organic soils, total phorate residues declined more quickly in the previously treated soils than in similar untreated soils, largely because of more rapid degradation of phorate sulfoxide and, especially, of phorate sulfone. It is concluded that accelerated degradation of these insecticides probably limits their performance in some circumstances and that further studies are needed to determine the extent of the phenomenon.
In 90 day feeding trials with male albino rats receiving < or = 15 mg/kg diet, no significant effect was observed on wt gain but there was a reduction in erythrocyte and brain cholinesterase activity.
Cotton foliage may be injured in high-rainfall conditions.
A contact and stomach poison with systemic activity in plants through root and foliar absorption.
1. INSURE THAT A CLEAR AIRWAY EXISTS BY ASPIRATION OF SECRETIONS IF NECESSARY. ADMIN OXYGEN BY MECHANICALLY ASSISTED PULMONARY VENTILATION IF RESPIRATION IS DEPRESSED. IMPROVE TISSUE OXYGENATION AS MUCH AS POSSIBLE BEFORE ADMIN ATROPINE TO MINIMIZE RISK OF VENTRICULAR FIBRILLATION. IN SEVERE POISONINGS, IT MAY BE NECESSARY TO SUPPORT PULMONARY VENTILATION MECHANICALLY FOR SEVERAL DAYS. 2. ADMIN ATROPINE SULFATE IV, OR IM IF IV INJECTION IS NOT POSSIBLE. ... IN MODERATELY SEVERE POISONING: ADULT DOSAGE AND CHILDREN OVER 12 YR: 0.4-2.0 MG REPEATED EVERY 15 MIN UNTIL ATROPINIZATION IS ACHIEVED. MAINTAIN ATROPINIZATION WITH REPEATED DOSAGE OF 0.02-0.05 MG/KG BODY WEIGHT. /ORGANOPHOSPHATE PESTICIDES/
2. SEVERELY POISONED INDIVIDUALS MAY EXHIBIT REMARKABLE TOLERANCE TO ATROPINE; TWO OR MORE TIMES THE DOSAGES SUGGESTED ABOVE MAY BE NEEDED. THE DOSE OF ATROPINE MAY BE INCREASED AND THE DOSING INTERVAL DECREASED AS NEEDED TO CONTROL SYMPTOMS. CONTINUOUS INTRAVENOUS INFUSION OF ATROPINE MAY BE NECESSARY WHEN ATROPINE REQUIREMENTS ARE MASSIVE. REVERSAL OF MUSCARINIC SYMPTOMS AND SIGNS, NOT AN ARBITRARY DOSE LIMIT, IS THE DESIRED END-POINT. PRESERVATIVE-FREE ATROPINE PRODUCTS SHOULD BE USED WHENEVER POSSIBLE. NOTE: PERSONS NOT POISONED OR ONLY SLIGHTLY POISONED BY ORGANOPHOSPHATES MAY DEVELOP SIGNS OF ATROPINE TOXICITY FROM SUCH LARGE DOSES. FEVER, MUSCLE FIBRILLATIONS, AND DELIRIUM ARE THE MAIN SIGNS OF ATROPINE TOXICITY. IF THESE APPEAR WHILE THE PATIENT IS FULLY ATROPINIZED, ATROPINE ADMINISTRATION SHOULD BE DISCONTINUED, AT LEAST TEMPORARILY, WHILE THE SEVERITY OF POISONING IS REEVALUATED. /ORGANOPHOSPHATE PESTICIDES/
3. DRAW BLOOD SAMPLE (HEPARINIZED) FOR CHOLINESTERASE ANALYSIS BEFORE ADMINISTRATION OF PRALIDOXIME, WHICH TENDS TO REVERSE THE CHOLINESTERASE DEPRESSION. 4. ADMIN PRALIDOXIME (PROTOPAM, 2-PAM) IN CASES OF SEVERE POISONING ... IN WHICH RESP DEPRESSION, MUSCLE WEAKNESS & TWITCHINGS ARE SEVERE. ... ADULT DOSAGE AND CHILDREN OVER 12): GIVE 1.0-2.0 G IV @ NO MORE THAN 0.2 G/MIN. CHILD'S DOSE (UNDER 12 YR): GIVE 20-50 MG/KG (DEPENDING ON SEVERITY) IV, INJECTING NO MORE THAN HALF TOTAL DOSE/MIN. DOSAGE ... MAY BE REPEATED IN 1-2 HR THEN @ 10-12 HR INTERVAL IF NEEDED. IN VERY SEVERE POISONINGS, DOSAGE ... MAY BE DOUBLED. /ORGANOPHOSPHATE PESTICIDES/
4. BE PREPD TO ASSIST PULMONARY VENTILATION MECHANICALLY IF RESP ... DEPRESSED ... . 5. IN PATIENTS WHO HAVE BEEN POISONED BY ORGANOPHOSPHATE CONTAMINATION OF SKIN, CLOTHING, HAIR, AND/OR EYES, DECONTAMINATION MUST PROCEED CONCURRENTLY WITH WHATEVER RESUSCITATIVE AND ANTIDOTAL MEASURES ARE NECESSARY TO PRESERVE LIFE. ... 6. IF ... INGESTED IN QUANTITY PROBABLY SUFFICIENT TO CAUSE POISONING, THE STOMACH AND INTESTINE MUST BE EMPTIED. A. EMPTY THE STOMACH BY INTUBATION, ASPIRATION, AND LAVAGE, USING SLURRY OF ACTIVATED CHARCOAL IN ISOTONIC SALINE. RIGOROUS PRECAUTIONS MUST BE TAKEN TO PROTECT THE AIRWAY FROM ASPIRATION OF REGURGITATED. IF VICTIM IS UNCONSCIOUS OR OBTUNDED, INSERT A CUFFED ENDOTRACHEAL TUBE PRIOR TO GASTRIC INTUBATION. KEEP VICTIM'S HEAD BELOW LEVEL OF STOMACH DURING GASTRIC INTUBATION AND LAVAGE ... . KEEP VICTIM'S HEAD TURNED TO THE LEFT. /ORGANOPHOSPHATE PESTICIDES/
For more Antidote and Emergency Treatment (Complete) data for MEPHOSFOLAN (8 total), please visit the HSDB record page.
9e-05
HEAST Current
0.0009
HEAST Current
LD50 Rat oral 8.9 mg/kg
LD50 Rabbit albino dermal 9.7 mg/kg
LD50 Mouse albino oral 11.3 mg/kg
LD50 (24 hr) Albino rabbit male percutaneous 28.7 mg technical/kg
5.70e+00
7.40e+01
1.80e+00
1.00e+01
2.60e-03
9e-05
1.70e+01
2.20e+02
5.40e+00
1.00e+01
9e-05
Volatile
Releases of CERCLA hazardous substances are subject to the release reporting requirement of CERCLA section 103, codified at 40 CFR part 302, in addition to the requirements of 40 CFR part 355. Mephosfolan is an extremely hazardous substance (EHS) subject to reporting requirements when stored in amounts in excess of its threshold planning quantity (TPQ) of 500 lbs.
25% W/V EC
2% granules
EC (250 or 750 g ai/l); GR (20-100 g/kg).
Phosphoramidic acid, N-(4-methyl-1,3-dithiolan-2-ylidene)-, diethyl ester: ACTIVE
Introduced in 1963 by Cyanamid International under the code number EI 47470, trademark cytrolane ... .
Insecticidal contact and stomach poison with systemic activity.