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Home > Encyclopedia > Crufomate

Crufomate

pharmaceutical raw materials
Crufomate structure

Crufomate 

structure
  • CAS No:

    299-86-5

  • Formula:

    C12H19ClNO3P

  • Chemical Name:

    Crufomate

  • Synonyms:

    Phosphoramidic acid,N-methyl-,2-chloro-4-(1,1-dimethylethyl)phenyl methyl ester;Phosphoramidic acid,methyl-,4-tert-butyl-2-chlorophenyl methyl ester;Phosphoramidic acid,methyl-,2-chloro-4-(1,1-dimethylethyl)phenyl methyl ester;Dowco 132;4-tert-Butyl-2-chlorophenyl methyl N-methylphosphoramidate;4-tert-Butyl-2-chlorophenyl methyl methylphosphoramidate;Crufomate;Montrel;Ruelene;Ruelene drench;Amidophos;Amidofos;4-tert-Butyl-2-chlorophenyl N-methyl O-methylphosphoramidate;Crufomat;NSC 253463;12676-14-1;150402-57-6

  • Categories:

    Agrochemicals  >  Pesticide Intermediates

Description

Crufomate is a white crystalline solid; the commercial product is a yellow oil.


Crufomate is a white crystalline solid Mp: 61.5°C. The commercial product is a yellow oil. A phosphoramidate insecticide.|WHITE CRYSTALS.|White, crystalline solid in pure form. The commercial product is a yellow oil.|White, crystalline solid in pure form. [pesticide] [Note: Commercial product is a yellow oil.]


Crufomate is a white crystalline solid Mp: 61.5°C. The commercial product is a yellow oil. A phosphoramidate insecticide.|Crufomate is an alkylbenzene.

Crufomate Basic Attributes

291.71

291.71

206-083-1

V82Q65924L

1143

253463

2783

DTXSID1037515

WHITE CRYSTALLINE SOLID|CRYSTALS FROM PETROLEUM ETHER|Colorless|White, crystalline solid in pure form [Note: Commercial product is a yellow oil].

29299090

Characteristics

47.6

3.33

Crufomate is a white crystalline solid Mp: 61.5°C. The commercial product is a yellow oil. A phosphoramidate insecticide.

1.1618 g/cm3 @ Temp: 70 °C

60-60.5 °C

117-118 °C @ Press: 0.01 Torr

155.3±30.7 °C

1.501

4.975g/L(temperature not stated)

Pesticides of any degree of toxicity should be transported in containers which are clearly labelled, leak-proof, and not easily damaged. They should never be transported /or stored/ beside, or above any type of food, and all spillages should be immediately reported. /Pesticides/

Vapour pressure, Pa at 25°C: 0.106

Oral-rat LD50: 460 mg/kg

Decomposes toxic phosphorus oxide, chloride and nitrogen oxide by heating

BOILING POINT: 117-118 °C @ 0.01 MM HG; INDEX OF REFRACTION: 1.5142 @ 20 °C/D /TECHNICAL PRODUCT/|YELLOW OIL /COMMERCIAL RUELENE/

No rapid reaction with air No rapid reaction with water

Amines, Phosphines, and Pyridines

CRUFOMATE is combustible; liquid formulations containing organic solvents may be flammable. Incompatible with strongly basic and strongly acidic materials. Unstable over long periods in aqueous preparations or above 140° F. Emits toxic fumes of POx, Cl2 and NOx when heated to decomposition (Hazardous Chemicals Desk Reference p. 272 (1987)).

Combustible Solid

Safety Information

III

6

UN2783 (solid)

21/22-50/53

36/37-60-61

TB3850000

Xn,N

The warehouse is ventilated, low temperature and dry; stored and transported separately from food materials

Unstable over long periods in aqueous preparations or above 140 degrees F.

P273-P280-P501

H302 + H312-H410

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.|All organic pesticides, whether of botanical or synthetic origin, can be destroyed by incineration. /Organic pesticides/|Manufacturers or formulators of very large amounts of pesticides may find it advantageous to build incinerators adequate to destroy all organic pesticides and equipped with scrubbers to remove acid wastes. /Organic pesticides/

Strongly alkaline & strongly acidic media. [Note: Unstable over long periods in aqueous preparations or above 140 °F.]

Combustible. Liquid formulations containing organic solvents may be flammable.

|Warning|H302: Harmful if swallowed [Warning Acute toxicity, oral]|P264, P270, P273, P280, P301+P312, P302+P352, P312, P322, P330, P363, P391, and P501|P260, P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P340, P305+P351+P338, P309+P311, P312, P322, P330, P332+P313, P337+P313, P363, P403+P233, P405, and P501

Skin: Wear appropriate personal protective clothing to prevent skin contact. Eyes: Wear appropriate eye protection to prevent eye contact. Wash skin: The worker should immediately wash the skin when it becomes contaminated. Remove: Work clothing that becomes wet or significantly contaminated should be removed and replaced. Change: Workers whose clothing may have become contaminated should change into uncontaminated clothing before leaving the work premise. (NIOSH, 2016)|Wear appropriate personal protective clothing to prevent skin contact.|Wear appropriate eye protection to prevent eye contact.|Respiratory protection (supplied-air respirator with full facepiece or self-contained breathing apparatus) should be available where these compounds are manufactured or used and should be worn in case of emergency and overexposure. /Phosphorus compounds/|WORKERS HANDLING AND APPLYING ORGANOPHOSPHATE PESTICIDES (OPP) MUST ... BE GIVEN PERSONAL PROTECTIVE EQUIPMENT COMPRISING OVERALLS MADE OF A TIGHT FABRIC OR POLYVINYL CHLORIDE, GLOVES, AND RUBBER BOOTS. THEY MUST WEAR A RESPIRATOR WITH AN ACTIVATED-CARBON GAS FILTER CARTRIDGE AFFORDING PROTECTION FOR A DETERMINED NUMBER OF WORKING HOURS. THE EYES SHOULD BE PROTECTED BY GOGGLES. THE SIGNALMEN FOR AERIAL DUSTING OPERATIONS SHOULD BE EQUIPPED WITH A HAT AND CAPE MADE OF POLYVINYL CHLORIDE OR A FABRIC IMPREGNATED WITH A WATER REPELLENT. /PESTICIDES, ORGANOPHOSPHORUS/|(See protection codes)

If material on fire or involved in fire: Extinguish fire using agent suitable for type of surrounding fire. (Material itself does not burn or burns with difficulty.) Use water in flooding quantities as fog. Use "alcohol" foam, carbon dioxide or dry chemical. /Organophosphorus pesticides, solid, NOS/

The worker should immediately wash the skin when it becomes contaminated.|Work clothing that becomes wet or significantly contaminated should be removed and replaced.|SRP: Contaminated protective clothing should be segregated in such a manner so that there is no direct personal contact by personnel who handle, dispose, or clean the clothing. Quality assurance to ascertain the completeness of the cleaning procedures should be implemented before the decontaminated protective clothing is returned for reuse by the workers. Contaminated clothing should not be taken home at end of shift, but should remain at employee's place of work for cleaning.|Workers whose clothing may have become contaminated should change into uncontaminated clothing before leaving the work premises.|For more Preventive Measures (Complete) data for RUELENE (12 total), please visit the HSDB record page.

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.

Recommended Exposure Limit: 10 Hr Time-Weighted Avg: 5 mg/cu m.|Recommended Exposure Limit: 15 Min Short-Term Exposure Limit: 20 mg/cu m.

Personal protection: complete protective clothing including self-contained breathing apparatus. Sweep spilled substance into sealable containers. If appropriate, moisten first to prevent dusting. Carefully collect remainder. Then store and dispose of according to local regulations. Do NOT wash away into sewer.

Separated from strong bases, strong acids and food and feedstuffs. Well closed. Keep in a well-ventilated room.

Evaporation at 20 °C is negligible; a harmful concentration of airborne particles can, however, be reached quickly on spraying or when dispersed, especially if powdered.

The substance is irritating to the eyes, skin and respiratory tract. The substance may cause effects on the nervous system. This may result in convulsions and respiratory failure. Cholinesterase inhibition. The effects may be delayed. Medical observation is indicated.

NO open flames.

AVOID EXPOSURE OF ADOLESCENTS AND CHILDREN!

Avoid inhalation of dust and mist. Use local exhaust or breathing protection.

Protective gloves. Protective clothing.

Wear face shield or eye protection in combination with breathing protection if powder.

Samples of sediment from the Upper Great Lakes were collected (number unknown) during the summer of 1974 for analysis. Levels of ruelene were not found above 0.1 ppm in the sediment(1).

Samples of seston (suspended particulate material consisting of plankton and both inorganic and organic detrital material) from the Upper Great Lakes were collected (number unknown) during the summer of 1974 for analysis. Levels of ruelene were not found to be 500 pg in the seston(1).

Toxicity

highly toxic

SINGLE ORAL DOSES OF RUELENE WERE ADMIN TO RATS TOGETHER WITH EACH OF THE 14 THEN-COMMERCIAL CHOLINESTERASE-INHIBITING INSECTICIDES. NO COMBINATION PRODUCED GREATER THAN ADDITIVE RATIOS OF EXPECTED TO OBSERVED LD50 VALUES EXCEPT RUELENE WITH MALATHION, WHERE THE RATIO WAS 5:3.|DO NOT USE IN CONJUNCTION WITH OR WITHIN A FEW DAYS OF ... ANY OTHER CHOLINESTERASE INHIBITING CMPD. (AVOID USE WITH PHENOTHIAZINE, PHENOTHIAZINE TRANQUILIZERS). /COUMAPHOS/|Some phenothiazines may antagonize & some may potentiate the toxic anticholinesterase effects of ... /organophosphorus insecticides/. /Organophosphate cholinesterase inhibitors/|In long term therapy, adrenocorticoids antagonize the antiglaucoma effects of anticholinesterases (incr ocular pressure). ... Anticholinergics antagonize the miotic (antiglaucoma) & other muscarinic effects of anticholinesterases on the autonomic & central nervous systems. Tricyclic antidepressants (anticholinergic effects) antagonize the antiglaucoma (miotic) effects of anticholinesterases in glaucoma. ... Antihistamines with anticholinergic effects antagonize the miotic (antiglaucoma) & CNS effects of anticholinesterases. Anticholinesterases potentiate tranquilizing & behavioral changes induced by antihistamines. The actions of anticholinesterase agents on autonomic effector cells, & to some extent those on CNS, are antagonized by atropine, an antidote of choice. Barbiturates are potentiated by anticholinesterases. ... Dexpanthenol potentiates the effects of anticholinesterases. Fluorophosphate insecticides potentiate the effects of other anticholinesterases. /Anticholinesterases/|For more Interactions (Complete) data for RUELENE (6 total), please visit the HSDB record page.

LD50 Rat (female) oral 460 mg/kg|LD50 Rat (male) oral 635 mg/kg|LD50 rat oral 770 mg/kg

Young persons under 18 yr, expectant or nursing mothers, /alcoholics/, or persons for whom work with toxic chemicals is contraindicated on account of their state of health /are at elevated risk from the toxic effects of organophosphorus pesticides. Those individuals with/ organic diseases of the CNS, mental disorders & epilepsy, pronounced endocrine & vegetative disorders, pulmonary tuberculosis, bronchial asthma, chronic respiratory diseases, cardiovascular diseases and circulatory disorders, gastrointestinal diseases (peptic ulcer), gastroenterocolitis, diseases of the liver & kidneys, eye diseases (chronic conjunctivitis and keratitis) /are at elevated risk from exposure/. /Organophosphorus pesticides/|Those individuals who are exposed to organophosphorus pesticides with pre-existing/ 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) /are at elevated risk from exposure/. 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/

Ruelene's former production as an insecticide for cattle grub control(1) resulted in its release to the environment(SRC).

TERRESTRIAL FATE: Based on a recommended classification scheme(1), an estimated Koc value of 1,700(SRC), determined from an experimental log Kow(2,SRC) and a recommended regression-derived equation(3), indicates that ruelene is expected to have low mobility in soil(SRC). Volatilization of ruelene from moist soil surfaces is not expected(SRC) given an estimated Henry's Law constant of 2.5X10-9 atm-cu m/mole(SRC), using a fragment constant estimation method(4). Ruelene is not expected to volatilize from dry soil surfaces based on an estimated vapor pressure of 3.8X10-5 mm Hg(SRC), determined from a fragment constant method(5). Biodegradation data for ruelene are not available(SRC).|AQUATIC FATE: Based on a recommended classification scheme(1), an estimated Koc value of 1,700(SRC), determined from an experimental log Kow(2,SRC) and a recommended regression-derived equation(3), indicates that ruelene is expected to adsorb to suspended solids and sediment in water(SRC). Ruelene is not expected to volatilize from water surfaces(3,SRC) based on an estimated Henry's Law constant of 2.5X10-9 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). According to a classification scheme(5), an estimated BCF value of 230(3,SRC), from an experimental log Kow(2,SRC), suggests that bioconcentration in aquatic organisms is high(SRC). Biodegradation data for ruelene are not available(SRC).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), ruelene, which has an estimated vapor pressure of 3.8X10-5 mm Hg at 25 °C(2,SRC), will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase ruelene 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 about ll hours(3,SRC). Particulate-phase ruelene may be physically removed from the air by wet and dry deposition(SRC).

The rate constant for the vapor-phase reaction of ruelene with photochemically-produced hydroxyl radicals has been estimated as 34X10-12 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1,SRC). This corresponds to an atmospheric half-life of about 11 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1,SRC).

An estimated BCF value of 230 was calculated for ruelene(SRC), using an experimental log Kow of 3.42(1,SRC) and a recommended regression-derived equation(2). According to a classification scheme(3), this BCF value suggests that bioconcentration in aquatic organisms is high(SRC).

The Koc of ruelene is estimated as approximately 1,700(SRC), using a measured log Kow of 3.42(1) and a regression-derived equation(2,SRC). According to a recommended classification scheme(3), this estimated Koc value suggests that ruelene is expected to have low mobility in soil(SRC).

The Henry's Law constant for ruelene is estimated as 2.5X10-9 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This value indicates that ruelene will be essentially nonvolatile from water surfaces(2,SRC). Ruelene's Henry's Law constant(1,SRC) indicates that volatilization from moist soil surfaces is not expected(SRC). Ruelene is not expected to volatilize from dry soil surfaces based on an estimated vapor pressure of 3.8X10-5 mm Hg(SRC), determined from a fragment constant method(3).

SURFACE WATER: Samples of water from the Upper Great Lakes were collected (number unknown) during the summer of 1974 for analysis. Levels of ruelene were not found above 0.025 ppm in water(1).|GROUNDWATER: Groundwater sampling for pesticides in the United States was conducted by the EPA from 1971 to 1991. Results showed that out of 6 wells sampled in California in 1987, no ruelene was detected(1). Between 1979 and 1984, 359 wells in all six regions of the Province of Ontario, Canada were sampled where contamination by pesticides was suspected. Samples were analyzed for ruelene but no positive detections of ruelene were obtained(2).|DRINKING WATER: Using data from the recovery of organophosphorous pesticides from treated XAD-2 resin extract, it was determined that 300 liters of Ottawa, Canada tap water had less than 1 ng/l ruelene present(1).

... WILL PASS INTO MILK OF TREATED ANIMALS.

Skin absorption, inhalation of dust, ingestion|Occupational exposure to ruelene may be through inhalation of dusts and dermal contact with this compound at workplaces where ruelene is produced or used. (SRC)

Drug Information

... AFTER SHEEP WERE GIVEN ORAL DOSES ... 85-95% OF DOSE WAS RECOVERED IN EXCRETA. ANALYSES SHOWED THAT THIS COMPD WAS DEGRADED TO INORGANIC PHOSPHATE WHICH WAS SUBSEQUENTLY INCORPORATED IN BONE. ... RUELENE WAS FED TO LAYING HENS AT ... 100 PPM FOR 7 DAYS. SIX METABOLITES WERE ISOLATED FROM EXCRETA. RESIDUES APPEARED IN EGG YOLKS 3-5 DAYS AFTER RETURN TO NORMAL FEED.|ORALLY TREATED SHEEP ELIMINATED 85% OF THE (32)P LABELED RUELENE IN THE URINE IN 24 HR ... THE WHOLE EXTRACT OF WHOLE BLOOD CONTAINED ... /RUELENE AND 4-TERT-BUTYL-2-CHLOROPHENYL METHYL PHOSPHORIC ACID/ AS WELL AS TRACES OF 3 MORE POLAR METABOLITES OF UNKNOWN STRUCTURE. RUELENE IS RAPIDLY DEGRADED IN POULTRY ... TO PHOSPHORIC ACID, AND INCORPORATED IN BONE TISSUE. OF THE ORAL DOSE GIVEN IN FEED ONLY 29% WAS EXCRETED AFTER 21 DAYS. AT LEAST SIX METABOLITES WERE ISOLATED IN EXCRETA ... THOSE ... IDENTIFIED WERE 4-TERT-BUTYL-2-CHLOROPHENYL METHYL PHOSPHORIC ACID AND METHYL PHOSPHORIC ACID.|AFTER ORAL ADMIN TO SHEEP ... (32)P RUELENE WAS READILY ABSORBED AND RAPIDLY EXCRETED MAINLY IN THE 24 HR URINE. 73% OF (32)P WAS EXCRETED IN THE URINE AND 14% IN THE FECES. PEAK BLOOD LEVELS OF (32)P OCCURRED FOUR HR AFTER DOSING. THE ULTIMATE BIOTRANSFORMATION PRODUCT OF (32)P RUELENE, INORGANIC PHOSPHATE PRODUCED BY HYDROLYSIS AND DEALKYLATION, ENTERED NORMAL BODY PROCESSES ... RESULTING IN SOME RETENTION OF (32)P IN ANIMALS. IN SHEEP DOSED WITH RUELENE, (32)P PERSISTED IN TISSUES FOR SEVERAL WEEKS, BUT NO /RUELENE/ WAS DETECTED ... AFTER 7 DAYS.|... WILL PASS INTO MILK OF TREATED ANIMALS.|For more Absorption, Distribution and Excretion (Complete) data for RUELENE (13 total), please visit the HSDB record page.

AFTER INCUBATION OF RUELENE WITH /SHEEP/ WHOLE BLOOD AND PLASMA, CHROMATOGRAPHY SHOWED PRESENCE OF DIMETHYLAMIDO PHOSPHORIC ACID AND PHENYLMETHYL PHOSPHORIC ACID. SEVERAL OTHER METABOLITES WERE FOUND BUT NOT COMPLETELY INDENTIFIED. RUELENE WAS FED TO LAYING HENS AT ... 100 PPM FOR 7 DAYS. 6 METABOLITES WERE ISOLATED FROM EXCRETA. ... O-METHYL-PHOSPHORIC ACID AND 4-TERT-BUTYL-2-CHLOROPHENYL METHYL PHOSPHORIC ACID WERE ... IDENTIFIED. SHEEP AND POULTRY HYDROLYZED BOTH ESTER AND AMIDE GROUPINGS AND FORMED ... CMPD THAT WERE EXCRETED VIA URINE OF SHEEP OR URINE & FECES OF POULTRY. ONE COMPD FROM SHEEP URINE WAS BELIEVED TO BE 4-T-BUTYL-2-CHLOROPHENYL DIHYDROGEN PHOSPHORIC ACID.|THE PRINCIPAL METABOLITE ISOLATED FROM INSECTS IS BELIEVED TO BE 4-TERT-BUTYL-2-CHLOROPHENYL DIHYDROGEN PHOSPHATE.|AFTER ORAL ADMIN TO SHEEP ... /OF/ (32)P RUELENE ... THE ULTIMATE BIOTRANSFORMATION PRODUCT OF (32)P RUELENE, INORGANIC PHOSPHATE PRODUCED BY HYDROLYSIS AND DEALKYLATION, ENTERED NORMAL BODY PROCESSES THUS RESULTING IN SOME RETENTION OF (32)P IN THE ANIMALS. IN SHEEP DOSED WITH (32)P RUELENE, (32)P PERSISTED IN THE TISSUES FOR SEVERAL WK, BUT NO (32)P WAS DETECTED AFTER 7 DAYS. THE EXTENT OF BIOTRANSFORMATION ... TO INORGANIC PHOSPHATE WAS INDICATED BY ORAL ADMIN OF (32)P PHOSPHORIC ACID TO ... SHEEP, WHEN 28-40% WAS EXCRETED MAINLY IN THE FECES, WHEREAS 85-95% OF AN ORAL DOSE OF (32)P RUELENE WAS EXCRETED MAINLY IN THE URINE.|METABOLITES IDENTIFIED FROM IN VITRO METABOLISM OF CRUFOMATE IN INTESTINAL SAC PREPN WERE 4-TERT-BUTYL-2-CHLOROPHENYL METHYL PHOSPHORAMIDATE; 2-CHLORO-4(2-HYDROXY-1,1-DIMETHYLETHYL)PHENYL METHYL METHYLPHOSPHORAMIDATE; 2-[3-CHLORO-4-[((METHOXY)METHYLAMINO) PHOSPHINYL]OXY]PHENYL-2-METHYLPROPIONIC ACID; 4-TERT-BUTYL-2-CHLOROPHENOL & ITS GLUCURONIDE & AROMATIC GLUCURONIDE OF 2-CHLORO-4(2-HYDROXY-1,1-DIMETHYLETHYL)PHENOL.|For more Metabolism/Metabolites (Complete) data for RUELENE (7 total), please visit the HSDB record page.

The signs of poisoning due to organophosphorus cmpd are those due to accumulation of acetylcholine & hence overstimulation of parasympathetic nervous system. It is usual to divide them under 3 headings: muscarinic, nicotinic & central. Muscarinic signs ... consist of hypersalivation, lacrimation, sweating & nasal discharge. Miosis, dyspnea, vomiting, diarrhea & frequency of urination ... Nicotinic effects consist of fasciculation of muscles, weakness & paralysis. Central nervous system effects include nervousness, apprehension, ataxia, convulsions & coma. Death is due to resp failure, or sometimes cardiac arrest. There is little difference between signs produced by different organophosphorus compounds, but route of absorption may influence one system more than another. /Organophosphorus cmpd/|The characteristic pharmacological effects of the anti-ChE agents are due primarily to the prevention of hydrolysis of ACh by AChE at sites of cholinergic transmission. Transmitter thus accumulates, and the response to ACh that is liberated by cholinergic impulses or that is spontaneously released from the nerve ending is enhanced. With most of the organophosphorus agents ... virtually all the acute effects of moderate doses are attributable to this action. /Anticholinesterase agents/|The cardiovascular actions of anticholinesterase agents are complex, since they reflect both ganglionic and postganglionic effects of accumulated ACh on the heart and blood vessels. The predominant effect on the heart from the peripheral action of accumulated ACh is bradycardia, resulting in a fall in cardiac output. Higher doses usually cause a fall in blood pressure, often as a consequence of effects of anticholinesterase agents on the medullary vasomotor centers of the CNS. /Anticholinesterase agents/|Organophosphorus derivatives act by combining with and inactivating the enzyme acetylcholinesterase. ... 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/|For more Mechanism of Action (Complete) data for RUELENE (7 total), please visit the HSDB record page.

Exposure Routes: inhalation, skin absorption, ingestion, skin and/or eye contact Symptoms: Irritation eyes, skin, respiratory system; wheezing, dyspnea (breathing difficulty); blurred vision, lacrimation (discharge of tears); sweating; abdominal cramps, diarrhea, nausea, anorexia Target Organs: Eyes, skin, respiratory system, blood cholinesterase (NIOSH, 2016)

Eye: If this chemical contacts the eyes, immediately wash the eyes with large amounts of water, occasionally lifting the lower and upper lids. Get medical attention immediately. Contact lenses should not be worn when working with this chemical. Skin: If this chemical contacts the skin, immediately wash the contaminated skin with soap and water. If this chemical penetrates the clothing, immediately remove the clothing, wash the skin with soap and water, and get medical attention promptly. Breathing: If a person breathes large amounts of this chemical, move the exposed person to fresh air at once. If breathing has stopped, perform mouth-to-mouth resuscitation. Keep the affected person warm and at rest. Get medical attention as soon as possible. Swallow: If this chemical has been swallowed, get medical attention immediately. (NIOSH, 2016)|(See procedures)


Fresh air, rest. Refer for medical attention.


Remove contaminated clothes. Rinse and then wash skin with water and soap. Refer for medical attention .


First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.

A comatose patient who is diaphoretic, has pinpoint pupils and the odor of an insecticide on clothing or breath, and is noted to have muscle fasciculations represents the classic presentation of organophosphate poisoning. ... Specific steps in management include the following. 1. Decontamination. ... 2 Airway. Establish an airway if necessary. ... 3. Respiratory Status. Respiratory distress, in fact, is commonly found in these patients from multiple causes. ... 4. Cardiac Monitoring. ... 5. Cholinesterase Level. ... 6. Pralidoxime. Pralidoxime is the treatment of choice for organophosphate poisoning and should be used for nearly all patients with clinically significant orgnophosphate poisoning, particularly whose patients with muscular fasciculations and weakness. ... 7. Atropine. Atropine is the physiologic antidote for organophosphate poisoning. A trial dose of atropine should be instituted on clinical ground when one suspects organophosphate intoxication. /Organophosphate poisoning/|For immediate first aid: ensure that adequate decontamination has been carried out. If victim is not breathing, start artificial respiration, preferably with a demand-valve resuscitator, bag-valve-mask device, or pocket mask as trained. Perform CPR if necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep victim quiet and maintain normal body temperature. Obtain medical attention. /Organophosphates and related compounds/|For basic treatment: Establish a patent airway. Suction if necessary. Aggressive airway control may be needed. Watch for signs of respiratory insufficiency and assist ventilations if necessary. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... Monitor for shock and treat if necessary ... Anticipate seizures and treat if necessary ... For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with normal saline during transport ... Do not use emetics. For ingestion, rinse mouth and administer ... water for dilution if the patient can swallow, has a strong gag reflex, and does not drool. Administer activated charcoal ... /Organophosphates and related compounds/|Preservative-free atropine should be used to avoid toxicity from preservative agents. Mydriasis may occur early in the administration of atropine; however the endpoint for atropine administration is the drying of pulmonary secretions. /Organophosphates and related compounds/|For more Antidote and Emergency Treatment (Complete) data for RUELENE (6 total), please visit the HSDB record page.

HUMAN TEST SUBJECTS INGESTING 200 MG CRUFOMATE/DAY FOR 7 DAYS (3 MG/KG/DAY) DID NOT EXHIBIT ANY CHOLINESTERASE DEPRESSION OR OTHER SYMPTOMS.|SYMPTOMATOLOGY: 7. DIFFICULTY IN BREATHING, EXCESSIVE SECRETION OF SALIVA & OF RESP TRACT MUCUS, ORONASAL FROTHING, CYANOSIS, PULMONARY RALES & RHONCHI & HYPERTENSION, (PRESUMABLY DUE TO ASPHYXIA). 8. RANDOM JERKY MOVEMENTS, INCONTINENCE, CONVULSIONS, & COMA. 9. DEATH PRIMARILY DUE TO RESP ARREST ARISING FROM FAILURE OF RESP CENTER, PARALYSIS OF RESP MUSCLES, INTENSE BRONCHOCONSTRICTION OR ALL THREE. /PARATHION/|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/|All the organophosphorus insecticides have a cumulative effect by progressive inhibition of cholinesterase ... /Organophosphorus insecticides/|For more Human Toxicity Excerpts (Complete) data for RUELENE (21 total), please visit the HSDB record page.

crufomate

The substance can be absorbed into the body by inhalation of its aerosol, through the skin and by ingestion.|inhalation, skin absorption, ingestion, skin and/or eye contact

irritation eyes, skin, respiratory system; wheezing, dyspnea (breathing difficulty); blurred vision, lacrimation (discharge of tears); sweating; abdominal cramps, diarrhea, nausea, anorexia


Dizziness. Sweating. Laboured breathing. Nausea. Unconsciousness. Vomiting. Pupillary constriction, muscle cramp, excessive salivation.


MAY BE ABSORBED! Redness. Further see Inhalation.


Redness. Pain.

Eyes, skin, respiratory system, blood cholinesterase

Crufomate Use and Manufacturing

Methods of Manufacturing

REACTION OF 4-T-BUTYL-2-CHLOROPHENYL PHOSPHONYLDICHLORIDE WITH METHANOL & THEN WITH METHYLAMINE

Uses

Insecticide.

Production

(1972) 2.0X10+8 GRAMS (EST)

100% AS AN INSECTICIDE FOR CATTLE GRUBS, HORN FLIES, & LICE ON BEEF CATTLE & NON-LACTATING DAIRY CATTLE (1973)

READY TO USE POUR-ON (122 G AI/L); WORMER DRENCH (210 G AI/L); POUR OR SPRAY (250 G AI/L); FOR DIPPING VAT USE (375 G AI/L).

The WHO Recommended Classification of Pesticides by Hazard identifies Crufomate (technical grade) as an active ingredient believed to be obsolete or discontinued for use as a pesticide.|PRODUCT DISCONTINUED BY THE DOW CHEMICAL CO.|INCOMPATABILITIES: ... IT IS INCOMPATIBLE WITH ALKALINE PESTICIDES ... .|ORALLY EFFECTIVE AGAINST HAEMONCHUS CONTORTUS, OSTERTAGIA SPECIES, & TRICHOSTRONGYLUS SPECIES, BUT RELATIVELY INEFFECTIVE AGAINST MANY IMMATURE FORMS & NEMATODIURUS IN SHEEP. IN CATTLE WARBLE CONTROL THERE IS SEASONAL VARIATIONS IN TOXICITY WHICH APPEARS TO BE ASSOCIATED WITH DEATH & ABSORPTION OF LARVAE RATHER THAN TOXICITY OF INSECTICIDE PER SE. USE DRUG BEFORE LARVAE REACH GULLET & EPIDURAL AREAS. THIS IS SEPTEMBER FOR MOST OF USA, ITALY, BULGARIA, & IRELAND.|CRUFOMATE IS A SYSTEMIC INSECTICIDE & ANTHELMINTIC USED MAINLY FOR THE TREATMENT OF CATTLE AGAINST WARBLE FLIES, ECTOPARASITES & HELMINTHS. IT IS NOT USED IN CROP PROTECTION. ... NONHAZARDOUS TO WILDLIFE.

HPLC ANALYSIS OF TECHNICAL RUELENE INSECTICIDE.|A METHOD IS DESCRIBED ... THAT IS SUITABLE FOR RUELENE DETERMINATION IN THE ATMOSPHERE.|RUELENE WAS EXTRACTED BY AMBERLITE XAD-2 RESIN & THE ELUTED EXTRACT WAS ANALYZED BY GC.|HERL Method 022: Analysis of Water for Pesticides. The Sampling and Analysis of Water For Pesticides. GC with electron capture detection and flame photometric detection, surface water, detection limit not specified, units in ppb.|For more Analytic Laboratory Methods (Complete) data for RUELENE (6 total), please visit the HSDB record page.

TISSUE SAMPLE, EXTRACTION WITH ACETONITRILE & PETROLEUM ETHER, SEPARATION WITH ACETONITRILE, CHOLINESTERASE INHIBITION.

INSECTICIDES

Computed Properties

Molecular Weight:291.71
XLogP3:3.4
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:5
Exact Mass:291.0791082
Monoisotopic Mass:291.0791082
Topological Polar Surface Area:47.6
Heavy Atom Count:18
Complexity:319
Undefined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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