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모노크로토포스

Monocrotophos

HCID 5371562
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기본 정보개요이름 및 식별자물성안전 및 규제화학 및 산업관련 반응화합물 노트
부분 구조 검색유사 구조 찾기

기본 정보

CAS
6923-22-4
표준 SMILES
CNC(=O)/C=C(\C)OP(=O)(OC)OC
InChIKey
KRTSDMXIXPKRQR-AATRIKPKSA-N
분자식
C7H14NO5P
평균 분자량
223.16 g/mol
단동위원소 질량
223.06095954

개요

Monocrotophos appears as colorless crystals with a mild ester odor, commercial product is a reddish-brown solid. Used as a fast acting insecticide with both systemic and contact action against a wide range of pests on cotton, sugar cane, tobacco, potatoes, peanuts, tomatoes, and ornamentals. Very toxic.

이름 및 식별자

우선 이름
Monocrotophos
IUPAC
dimethyl [(E)-4-(methylamino)-4-oxobut-2-en-2-yl] phosphate
현지명
모노크로토포스
영어명
Monocrotophos
분자식
C7H14NO5P
분자량
223.16

이름 및 동의어

MONOCROTOPHOSAzodrin6923-22-4NuvacronMonocronCorophosMonostarParryfosApadrinMonocilBilobornBilobran
이름 더 보기
모노크로토포스3-하이드록시-N-메틸-시스-크로톤아미드의디메틸인산염누바크론모노크로토포스시)-N-메틸이소크로톤아미드아조드린CROTONSufosBALWANAPARINHUKRONCROTOSC 1414SD 9129
CrisodrinHazodrinMonodrinPillardrinPlantdrinSusvinUlvairMonocil 40

데이터베이스 식별자

CAS
6923-22-4、919-44-8
PubChem CID
5371562
DTXSID
DTXSID9034816
ChEMBL
CHEMBL2272785
ChEBI
CHEBI:38728
UNII
5Q3PE07Z18
EC Number
230-042-7
Nikkaji
J3.092I、J857E

물성

구조 계산 물성

XLogP
-0.2
극성 표면적
73.9 Ų
수소 결합 공여자 수
1
수소 결합 수용자 수
5
회전 가능 결합 수
5
무거운 원자 수
14
형식 전하
0
복잡도
267

실험 및 물리화학적 성질

SpringerMaterials PropertiesFusion temperature
Pesticides · 4건

Acaricides, Insecticides

Active substance -> EU Pesticides database: Not approved

Pesticides -> Organophosphate Insecticides

Pesticide (Monocrotophos) -> USDA PDB

LogP · 3건

log Kow = -0.20

-0.20

-0.2 (calculated)

OdorMild, ester odor.
Density · 3건

1.22 kg/l at 20 °C

Density (at 20 °C): 1.22 g/cm³

1.22 @ 20°C

Color/Form · 2건

Reddish brown solid

Colorless to reddish-brown solid.

Solubility · 6건

Miscible (NIOSH, 2024)

SOL IN WATER, ETHANOL, PETROLEUM ETHER, ACETONE /TECHNICAL GRADE/

MISCIBLE WITH WATER; SOL IN ACETONE, ETHANOL; PRACTICALLY INSOL IN DIESEL OILS, KEROSINE.

Solubility (20 °C) 1 kg/kg water; 700 g/kg acetone; 800 g/kg dichloromethane; 1 kg/kg methanol; 250 g/kg octan-1-ol; 60 g/kg toluene.

Sparingly sol in xylene.

In water 100% at 20 °C; in methanol 100%, acetone 70%, n-octanol 25%, toluene 6% (all at 20 °C). Sparingly soluble in kerosene and diesel oil.

안전 및 규제

안전 정보는 참고용이며, 공급업체의 물질안전보건자료(SDS), 관련 법규 및 전문가 평가를 대체하지 않습니다.

GHS 분류

GHS Classification · 6건

Danger

H300: Fatal if swallowed [Danger Acute toxicity, oral]

P203, P260, P262, P264, P270, P271, P273, P280, P284, P301+P316, P302+P352, P304+P340, P316, P318, P320, P321, P330, P361+P364, P391, P403+P233, P405, and P501 (click each P-code to see the statement)

Danger

H300+H330 (27.1%): Fatal if swallowed or if inhaled [Danger Acute toxicity, oral; acute toxicity, inhalation]

P203, P260, P262, P264, P270, P271, P273, P280, P284, P301+P316, P302+P352, P304+P340, P316, P318, P320, P321, P330, P361+P364, P391, P403+P233, P405, and P501 (click each P-code to see the statement)

유해성 정보

Regulatory Information · 3건

Hazard Traits - Environmental tox

Regulation (EC) No 1107/2009 (amended)

2002/2076

Other Safety InformationIMAP assessments - Phosphoric acid, dimethyl 1-methyl-3-(methylamino)-3-oxo-1-propenyl ester, (E)-: Human health tier I assessment
DOT LabelPoison
Fire Hazards · 2건

Wear positive pressure breathing apparatus and full protective clothing. Container may explode in heat of fire. Toxic fumes evolved when heated to decomposition. Incompatible with alkaline compounds. Unstable in aqueous solution above pH 7.0; in low molecular weight alcohols and glycols. Stable in ketones and higher molecular weight alcohols and glycols. Stable when stored in glass or polyethylene containers. Relatively stable in sunlight. Keep away from temperatures above 80F; do not store below 70F. Corrosive to black iron, drum steel, stainless steel 304 and brass, but not to glass, aluminum, or stainless steel 316. (EPA, 1998)

Combustible. Liquid formulations containing organic solvents may be flammable. Gives off irritating or toxic fumes (or gases) in a fire. Risk of fire and explosion if formulations contain flammable/explosive solvents.

화학 및 산업

약리 정보

Mechanism of Action · 5건

Cholinesterase inhibitor.

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/

For more Mechanism of Action (Complete) data for MONOCROTOPHOS (8 total), please visit the HSDB record page.

Biological Half-LifeAFTER INJECTION INTO STEMS ... (32)P AZODRIN ... TRANSLOCATED IN BEAN PLANTS ANDPERSISTED FOR SEVERAL WK UNDER GREENHOUSE CONDITIONS. HALF-LIFE ... 14 DAYS.
Metabolism/Metabolites · 6건

SIGNIFICANT AMT OF N-HYDROXYMETHYLAMIDE ANALOG OF AZODRIN APPEARED FOLLOWING ADMIN TO RATS OF ... AZODRIN ... AND UNSUBSTITUTED AMIDE ... /WAS ALSO PRESENT/. IN RATS ADMIN AZODRIN ONLY TRACE AMT OF AZODRIN ACID WERE DETECTED IN EXTRACTS, INDICATING MINIMAL HYDROLYTIC DEGRADATION BY AMIDASE ACTION. DIMETHYL PHOSPHATE & O-DEMETHYL AZODRIN WERE MAJOR DEGRADATION PRODUCTS OF AZODRIN. IT WAS FELT THAT DEGRADATION FOLLOWED FORMATION OF N-HYDROXYMETHYL AZODRIN ... . THE FINDING OF ONLY TRACE AMOUNTS OF N-DEMETHYL AZODRIN & THE STABILITY OF THE PURE COMPOUND SEEMED TO INDICATE THAT DEMETHYLATION WAS MINOR REACTION.

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화합물 노트

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이 페이지에서기본 정보개요이름 및 식별자물성안전 및 규제화학 및 산업관련 반응화합물 노트
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Corrosivity · 2건

Non-corrosive to aluminum.

CORROSIVE TO BLACK IRON, DRUM STEEL, STAINLESS STEEL 304 & BRASS.

Flash Point · 4건

Above 200F (EPA, 1998)

Above 200 °F, closed cup

>200 °F

>200 °F

Boiling Point · 6건

257 °F at 0.0005 mmHg (EPA, 1998)

125 °C @ 760 MM HG

at 0.00007kPa: 125 °C

257 °F at 0.0005 mmHg

125 °C @760 [mm Hg]

257 °F

Decomposition · 2건

WHEN HEATED TO DECOMPOSITION IT EMITS VERY TOXIC FUMES.

Decomposes > 38 °C, thermal runaway reactions can occur > 55 °C ... Decomposes on some inert materials (care should be taken when carrying out chromatography).

Melting Point · 6건

129 to 131 °F crystals; 77 to 86 °F commercial product (EPA, 1998)

54-55 °C

54 - 55 °C

54-55 °C

129 °F

129 °F

물리화학적 성질

녹는점
54 · 54-55°C
끓는 점
125 °C · 125°C (0.0005 torr)
밀도
1.33 · 1.3300
증기압
2.9 · 2.9×10-4 Pa (20 °C)
인화점
-18 °C · -18 °C
저장 조건
0 · 0-6°C
용해도
클로로포름(약간 용해됨), 메탄올(약간 용해됨)
산도 계수 (pKa)
13.06 · 13.06±0.46(Predicted)
물리적 상태
고체
수용성
녹는
BRN
8415832 · 8415832
Henry's Law Constant
1.5 · 1.5×107 mol/(m3Pa) at 25℃, HSDB (2015)
안정성
온도에 민감함
NIST
Monocrotophos(6923-22-4)
EPA
Monocrotophos (6923-22-4)

화학적 성질

Monocrotophos is a colorless to reddishbrown solid with a mild ester odor.

Fire Potential
AZODRIN 5 IS EXTREMELY FLAMMABLE.
Health Hazards · 1건

Monocrotophos is an organophosphorus pesticide. It is a cholinesterase inhibitor and acts on the nervous system. Extremely toxic; probable oral lethal dose to humans 5-50 mg/kg or between 7 drops and 1 teaspoon for a 70 kg (150 lb.) person. Repeated inhalation or skin contact with this material may, without symptoms, progressively increase susceptibility to poisoning. (EPA, 1998)

Hazards Summary · 1건

Inhalation of high concentrations may cause CNS effects; Cholinesterase inhibitor; [ICSC] 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]

DOT ID and Guide2783 152(organophosphorus pesticide, solid)
Reactive GroupAmides and Imides
EC ClassificationSymbol: T+, N; R: 24-26/28-50/53-68; S: (1/2)-36/37-45-60-61
UN ClassificationUN Hazard Class: 6.1; UN Pack Group: II
Special ReportsWHO/IPCS; Pesticide Residues in Food - 1991. Part II - Toxicology (1992)

안전 및 보호

Fire Fighting · 2건

Like other organophosphorus pesticides, move container from fire area if you can do so without risk. Fight fire from maximum distance. Dike fire control water for later disposal; do not scatter the material.

Use water spray, dry powder, foam, carbon dioxide.

First Aid Measures · 4건

Fresh air, rest. Half-upright position. Artificial respiration may be needed. Refer immediately for medical attention.

Remove contaminated clothes. Rinse and then wash skin with water and soap. Refer immediately for medical attention. Wear protective gloves when administering first aid.

Rinse with plenty of water (remove contact lenses if easily possible). Refer immediately for medical attention.

Rinse mouth. Give a slurry of activated charcoal in water to drink. Do NOT induce vomiting. Refer immediately for medical attention.

First Aid · 2건

Note: Monocrotophos is a cholinesterase inhibitor.

(General first aid procedures)

Safe StorageProvision to contain effluent from fire extinguishing. Separated from food and feedstuffs. Dry. Well closed. Keep in a well-ventilated room. Store in an area without drain or sewer access.
Exposure Control and Personal Protection · 1건

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]

Fire Fighting Procedures · 3건

Use water, foam, carbon dioxide, or dry chemical to extinguish fires. /Malathion/

AREA SURROUNDING FIRE SHOULD BE DIKED TO PREVENT WATER RUNOFF. /MALATHION/

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/

Storage Conditions · 4건

DO NOT STORE /AZODRIN 5/ BELOW 70 °F OR ABOVE 80 °F FOR PROLONGED PERIODS. AZODRIN 5 IS EXTREMELY FLAMMABLE.

Rooms used for storage only should be soundly constructed & fitted with secure locks. Floors should be kept clear & pesticides clearly identified. If repacking is carried out in storage rooms, adequate light should be available; floors should be impervious & sound ... . /Pesticides/

Pesticides containers must be provided with labels indicating the degree of toxicity of the product they contain. The labels must not only give a short description of how to use the prepn, but also state basic precautions to be taken when applying it. /Organophosphorus pesticides/

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/

Cleanup Methods · 3건

Spills of malathion on floors shall be absorbed with absorbing clay. Sweeping compound may be utilized to facilitate the removal of all visible traces of malathion contaminated clay. Equipment and fixtures contaminated with malathion shall be decontaminated with an alkaline solution (5% sodium hydroxide). /Malathion/

... Alternative treatment process for spent filter cake from malathion mfr requires the following steps: (1) hydrolysis; (2) steam stripping; (3) decantation; (4) composting; & (5) biological treatment. /Malathion/

Ultraviolet radiation in conjunction with ozone is a highly effective degradation technique for malathion ... /Malathion/

Nonfire Spill ResponseAs with other organophosphorus pesticides, do not touch spilled material; stop leak if you can do it without risk. Use water spray to reduce vapors.
Disposal Methods · 5건

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.

Hydrolysis: The treatment of this product with water produces hydrolysis @ a rate that is almost independent of pH in the pH range of 1-7 (50% hydrolyzed @ pH 1-7 in 22-23 days @ 38 °C). At higher pHs the rate of hydrolysis rapidly increases. Recommendable methods: Incineration & landfill. Peer-review: Large amt, incinerate in a unit with effluent gas scrubbing. (Peer-review conclusions of an IRPTC expert consultation (May 1985))

MALATHION MAY BE DISPOSED OF BY ABSORBING IN VERMICULITE, DRY SAND, EARTH, OR A SIMILAR MATERIAL ... & /DISPOSING OF SO AS TO MEET LOCAL, STATE, & FEDERAL REGULATIONS/. /MALATHION/

Incineration together with flammable solvent in furnace equipped with afterburner and scrubber is recommended. /Malathion/

For more Disposal Methods (Complete) data for MONOCROTOPHOS (9 total), please visit the HSDB record page.

Spillage Disposal · 1건

Personal protection: complete protective clothing including self-contained breathing apparatus. Do NOT let this chemical enter the environment. Sweep spilled substance into covered sealable, plastic containers. If appropriate, moisten first to prevent dusting. Carefully collect remainder. Then store and dispose of according to local regulations.

Preventive Measures · 5건

The worker should immediately wash the skin when it becomes contaminated.

Work clothing that becomes wet or significantly contaminated should be removed and replaced.

Workers whose clothing may have become contaminated should change into uncontaminated clothing before leaving the work premises.

In some situations where personnel may become accidently contaminated ... it is necessary to provide shower bath in addition to the usual washing facilities. Special arrangements for cleaning clothing & overalls may be necessary ... /Pesticides/

For more Preventive Measures (Complete) data for MONOCROTOPHOS (11 total), please visit the HSDB record page.

독성 정보

Treatment · 1건

If the compound has been ingested, rapid gastric lavage should be performed using 5% sodium bicarbonate. For skin contact, the skin should be washed with soap and water. If the compound has entered the eyes, they should be washed with large quantities of isotonic saline or water. In serious cases, atropine and/or pralidoxime should be administered. Anti-cholinergic drugs work to counteract the effects of excess acetylcholine and reactivate AChE. Atropine can be used as an antidote in conjunction with pralidoxime or other pyridinium oximes (such as trimedoxime or obidoxime), though the use of '-oximes' has been found to be of no benefit, or possibly harmful, in at least two meta-analyses. Atropine is a muscarinic antagonist, and thus blocks the action of acetylcholine peripherally.

Interactions · 4건

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/

BARBITURATES ARE POTENTIATED BY ANTICHOLINESTERASES. ALTHOUGH BARBITURATES MAY BE USED CAUTIOUSLY IN TREATING CONVULSIONS, EXTREME CARE IS ESSENTIAL IN HANDLING POISONINGS DUE TO ANTICHOLINESTERASES, PARTICULARLY ORGANOPHOSPHORUS PESTICIDES. ECHOTHIOPHATE, A CHOLINESTERASE INHIBITOR USED AS MIOTIC, POTENTIATES OTHER SUCH INHIBITORS ... USED FOR OTHER PURPOSES (ADDITIVE EFFECTS) OR POSSIBLY SYNERGISTIC. THOSE EXPOSED TO ORGANOPHOSPHATE INSECTICIDES MUST TAKE STRICT PRECAUTIONS. ... ORGANOPHOSPHORUS INSECTICIDES: ADDITIVE ANTICHOLINESTERASE EFFECTS. HAZARDOUS. PATIENTS ON ANTICHOLINESTERASES (EVEN TOPICAL, SUCH AS EYE DROPS) SHOULD AVOID AREAS WHERE ORGANOPHOSPHORUS INSECTICIDES ... RECENTLY ... USED. /ANTICHOLINESTERASE/

ANTICHOLINESTERASE (ORGANOPHOSPHORUS) INSECTICIDES ANTAGONIZE POLARIZING MUSCLE RELAXANTS. PHENOTHIAZINES /AND THIOXANTHENES/: ... MAY ENHANCE TOXIC EFFECTS OF ORGANOPHOSPHORUS INSECTICIDES. /INSECTICIDES, ORGANOPHOSPHORUS/

Target OrgansEyes, respiratory system, central nervous system, cardiovascular system, blood cholinesterase, reproductive system
Health Effects · 1건

Acute exposure to cholinesterase inhibitors can cause a cholinergic crisis characterized by severe nausea/vomiting, salivation, sweating, bradycardia, hypotension, collapse, and convulsions. Increasing muscle weakness is a possibility and may result in death if respiratory muscles are involved. Accumulation of ACh at motor nerves causes overstimulation of nicotinic expression at the neuromuscular junction. When this occurs symptoms such as muscle weakness, fatigue, muscle cramps, fasciculation, and paralysis can be seen. When there is an accumulation of ACh at autonomic ganglia this causes overstimulation of nicotinic expression in the sympathetic system. Symptoms associated with this are hypertension, and hypoglycemia. Overstimulation of nicotinic acetylcholine receptors in the central nervous system, due to accumulation of ACh, results in anxiety, headache, convulsions, ataxia, depression of respiration and circulation, tremor, general weakness, and potentially coma. When there is expression of muscarinic overstimulation due to excess acetylcholine at muscarinic acetylcholine receptors symptoms of visual disturbances, tightness in chest, wheezing due to bronchoconstriction, increased bronchial secretions, increased salivation, lacrimation, sweating, peristalsis, and urination can occur. Certain reproductive effects in fertility, growth, and development for males and females have been linked specifically to organophosphate pesticide exposure. Most of the research on reproductive effects has been conducted on farmers working with pesticides and insecticdes in rural areas. In females menstrual cycle disturbances, longer pregnancies, spontaneous abortions, stillbirths, and some developmental effects in offspring have been linked to organophosphate pesticide exposure. Prenatal exposure has been linked to impaired fetal growth and development. Neurotoxic effects have also been linked to poisoning with OP pesticides causing four neurotoxic effects in humans: cholinergic syndrome, intermediate syndrome, organophosphate-induced delayed polyneuropathy (OPIDP), and chronic organophosphate-induced neuropsychiatric disorder (COPIND). These syndromes result after acute and chronic exposure to OP pesticides.

Ecotoxicity Values · 5건

LC50 Gammarus fasciatus 0.3 mg/l/96 hr, 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 material 100%/

LC50 Fathead minnow greater than 50 mg/l/96 hr, wt 0.9 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 material, 100%/

LC50 Bluegill 12.1 mg/l/96 hr (95% confidence limit 7.2-10.1 mg/l) /as stated in source/, 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 material, 100%/

LC50 Rainbow trout 5.2 mg/l/96 hr, wt 0.5 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. /Dispersible liq, 3.2 lb/gal/

For more Ecotoxicity Values (Complete) data for MONOCROTOPHOS (22 total), please visit the HSDB record page.

Environmental Fate · 5건

TWO PLOTS OF MATURE VALENCIA ORANGE TREES ... SPRAYED WITH AZODRIN. ONE AT RATE OF 10 LB AND OTHER 1 LB TECHNICAL AZODRIN/ACRE. RESIDUE HALF-LIFE WAS 16 & 13 DAYS, RESPECTIVELY. AZODRIN PENETRATED INTO RIND RAPIDLY AND WAS NOT REMOVED BY WASHING FRUIT 12 DAYS AFTER TREATMENT.

Aquatic reactions: persistence in riverwater in a sealed glass jar under sunlight & artificial fluorescent light-initial concentration= 10 ug/l: % of original compound found after 1 hr 100; 1 wk 100; 2 wk 100; 4 wk 100; 8 wk 100.

TERRESTRIAL FATE: Based on a recommended classification scheme(1), an estimated Koc value of 19(SRC), determined from an experimental log Kow of -0.20(2,SRC) and a recommended regression-derived equation(3), indicates that monocrotophos is expected to have very high mobility in soil(SRC). Volatilization of monocrotophos from moist soil surfaces is not expected given an estimated Henry's Law constant of 6.5X10-13 atm-cu m/mole(SRC),determined from experimental values for vapor pressure, 2.2X10-6 mm Hg at 20 °C(4), and water solubility, 1.0X10+6 mg/l at 20 °C(5). Monocrotophos is not expected to volatilize from dry soil surfaces based on a measured vapor pressure of 2.2X10-6 mm Hg(4,SRC). Monocrotophos is rapidly degraded in soil with half-lives ranging from 1 to 5 days(4).

TERRESTRIAL FATE: The half-life of monocrotophos on foliage (cotton, corn, grass) ranged from 1.3 to 3.4 days(1).

For more Environmental Fate (Complete) data for MONOCROTOPHOS (6 total), please visit the HSDB record page.

Food Survey ValuesMonocrotophos was detected in agricultural commodities between October 1, 1981 and September 30, 1986 at concentrations ranging from 0.05 ppm to 1.0 ppm(1).
Adverse EffectsOther Poison - Organophosphate
Exposure Routes · 2건

The substance can be absorbed into the body by inhalation, through the skin and by ingestion.

inhalation, skin absorption, ingestion, skin and/or eye contact

Milk ConcentrationsGoats given labeled monocrotophos by mouth showed only traces of labeled material in milk.
Toxicity Summary · 1건

(E)-Monocrotophos is a cholinesterase or acetylcholinesterase (AChE) inhibitor. A cholinesterase inhibitor (or 'anticholinesterase') suppresses the action of acetylcholinesterase. Because of its essential function, chemicals that interfere with the action of acetylcholinesterase are potent neurotoxins, causing excessive salivation and eye-watering in low doses, followed by muscle spasms and ultimately death. Nerve gases and many substances used in insecticides have been shown to act by binding a serine in the active site of acetylcholine esterase, inhibiting the enzyme completely. Acetylcholine esterase breaks down the neurotransmitter acetylcholine, which is released at nerve and muscle junctions, in order to allow the muscle or organ to relax. The result of acetylcholine esterase inhibition is that acetylcholine builds up and continues to act so that any nerve impulses are continually transmitted and muscle contractions do not stop. Among the most common acetylcholinesterase inhibitors are phosphorus-based compounds, which are designed to bind to the active site of the enzyme. The structural requirements are a phosphorus atom bearing two lipophilic groups, a leaving group (such as a halide or thiocyanate), and a terminal oxygen.

Plant ConcentrationsLeaf surface residues of monocrotophos on mature cotton plants treated at 1.0 lb AI/acre were 12.8, 10.6, 6.3, and 4.3 mg/sq m at 0, 24, 48, and 72 hours after application(1).

규제 정보

FIFRA Requirements · 1건

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. Monocrotophos is found on List A, which contains most food use pesticides and consists of the 194 chemical cases (or 350 individual active ingredients) for which EPA issued registration standards prior to FIFRA, as amended in 1988. Case No: 0154; Pesticide type: insecticide (acaricide); Registration Standard Date: 09/13/85; 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): Monocrotophos; AI Status: The active ingredient is no longer contained in any registered pesticide products ... "cancelled."

안전 데이터

OEB
C
OEL
TWA: 0.25 mg/m3
wgk
3
rtecs
TC4375000
ridadr
UN 2783
독성
LD50 in male, female rats (mg/kg): 17, 20 orally; 126, 112 dermally (Gaines)
HS 번호
29241200
risk_code
24-26/28-50/53-68-67-65-38-11-36-20/21/22
hazard_code
T+;N,N,T+,Xn,F
safety_code
1/2-36/37-45-60-61-62-26-16
포장분류
II
위험 등급
6.1(a)
기존화학 물질
KE-11535
유해 물질 데이터
6923-22-4(Hazardous Substances Data)
함량 및 규제정보
물질구분: 금지물질; 혼합물(제품)함량정보: 모노크로토포스 및 이를 1% 이상 함유한 혼합물
유해화학물질 필터링
97-1-88;06-4-8

HOUSEFLIES & AMERICAN COCKROACHES ... METABOLIZED ... AZODRIN TO FORM N-HYDROXYMETHYL & N-DEMETHYLATED DERIVATIVES.

... ABSORBED AZODRIN WAS METABOLIZED MORE RAPIDLY IN HOUSEFLIES THAN IN WEEVILS. N-HYDROXYMETHYL AZODRIN WAS DETECTED AFTER 4-8 HR IN HOUSEFLIES BUT NOT UNTIL AFTER 24 HR IN WEEVILS. DIMETHYL PHOSPHATE WAS MAJOR HYDROLYSIS PRODUCT IN HOUSE FLIES; O-DEMETHYL AZODRIN PREDOMINATED IN WEEVILS.

In plants, N-hydroxy compound is formed in small amounts.

For more Metabolism/Metabolites (Complete) data for MONOCROTOPHOS (8 total), please visit the HSDB record page.

Metabolism of organophosphates occurs principally by oxidation, by hydrolysis via esterases and by reaction with glutathione. Demethylation and glucuronidation may also occur. Oxidation of organophosphorus pesticides may result in moderately toxic products. In general, phosphorothioates are not directly toxic but require oxidative metabolism to the proximal toxin. The glutathione transferase reactions produce products that are, in most cases, of low toxicity. Paraoxonase (PON1) is a key enzyme in the metabolism of organophosphates. PON1 can inactivate some organophosphates through hydrolysis. PON1 hydrolyzes the active metabolites in several organophosphates insecticides as well as, nerve agents such as soman, sarin, and VX. The presence of PON1 polymorphisms causes there to be different enzyme levels and catalytic efficiency of this esterase, which in turn suggests that different individuals may be more susceptible to the toxic effect of organophosphate exposure.

MeSH Pharmacological Classification · 4건

Drugs that inhibit cholinesterases. The neurotransmitter ACETYLCHOLINE is rapidly hydrolyzed, and thereby inactivated, by cholinesterases. When cholinesterases are inhibited, the action of endogenously released acetylcholine at cholinergic synapses is potentiated. Cholinesterase inhibitors are widely used clinically for their potentiation of cholinergic inputs to the gastrointestinal tract and urinary bladder, the eye, and skeletal muscles; they are also used for their effects on the heart and the central nervous system.

Pesticides designed to control insects that are harmful to man. The insects may be directly harmful, as those acting as disease vectors, or indirectly harmful, as destroyers of crops, food products, or textile fabrics.

A chemically heterogeneous group of drugs that have in common the ability to block oxidative deamination of naturally occurring monoamines. (From Gilman, et al., Goodman and Gilman's The Pharmacological Basis of Therapeutics, 8th ed, p414)

Chemical agents that increase the rate of genetic mutation by interfering with the function of nucleic acids. A clastogen is a specific mutagen that causes breaks in chromosomes.

Absorption, Distribution and Excretion · 5건

GOATS TREATED ORALLY WITH ... AZODRIN EXCRETED IN URINE HIGH PROPORTION OF ADMIN ... N-METHYL (14)C LABEL. TRACE AMT OF ... AZODRIN, N-HYDROXYMETHYLAMIDE ANALOG OF AZODRIN, AND UNSUBSTITUTED AMIDE WERE PRESENT IN URINE. LABELED CMPD APPEARED IN GOAT MILK AFTER TREATMENT WITH ... (14)C-LABELED ... AZODRIN. ... TRACES OF N-HYDROXYMETHYLAMIDE & UNSUBSTITUTED AMIDE WERE ALSO PRESENT.

AFTER INJECTION INTO STEMS ... (32)P AZODRIN ... TRANSLOCATED IN BEAN PLANTS AND PERSISTED FOR SEVERAL WK UNDER GREENHOUSE CONDITIONS. ... TRACES OF N-HYDROXYMETHYLAMIDE & UNSUBSTITUTED AMIDE WERE PRESENT AT 8 DAYS BUT ONLY AZODRIN ... PRESENT AFTER 20 DAYS.

Excretion of radioactive phosphorus by rats injected ip with (32)P monocrotophos was rapid. In 6 hr, 45% was excreted, and in 24 hr, 58.4 and 5.1% had been recovered from urine and feces, respectively.

When radioactive monocrotophos was applied to human skin, the rate of excretion was maximal during the first 24-48 hr period, and it decr only slightly during the third and fourth days. A total of 14.7% of the radioactivity was recovered in the urine within 120 hr and only a small correction factor was involved.

For more Absorption, Distribution and Excretion (Complete) data for MONOCROTOPHOS (13 total), please visit the HSDB record page.

Cellular LocationsCytoplasm

용도 및 제조

Uses · 6건

Used to kill insects and spider mites on cotton, sugarcane, peanuts, tobacco, and ornamentals; very toxic to birds and mammals. [EXTOXNET]

All uses cancelled by the EPA in 1988; [EXTOXNET]

Farming (Pesticides) [Category: Industry]

The active ingredient is no longer contained in any registered pesticide products ... "cancelled."

INSECTICIDE & ACARICIDE ON COTTON, POTATOES, PEANUTS, ORNAMENTALS, TOBACCO; & FOR SUGARCANE BORERS. /FORMER USE/

/Monocrotophos/ is a fast-acting systemic and contact insecticide of short persistence.

Consumption Patterns40% AS AN INSECTICIDE & ACARICIDE ON COTTON; 30% AS AN INSECTICIDE & ACARICIDE ON TOBACCO; AND 30% AS AN INSECTICIDE & ACARICIDE ON OTHER FIELD CROPS & VEGETABLES (1974).
Methods of Manufacturing · 2건

REACTION OF TRIMETHYL PHOSPHITE WITH N-METHYL ALPHA-CHLOROACETOACETAMIDE.

Monocrotophos may be made by the reaction of trimethyl phosphite with 2-chloro-N-methyl-3-oxobutyramide.

Formulations/Preparations · 5건

... CONCENTRATES (200, 400 & 600 G AI/L); 200 SCW & 400 SCW, WSC (200 & 400 G/L); 250 ULV, ULV CONCENTRATE (250 G/L); GRANULES (50 G/KG); 'NUVARON COMBI', EC MIXTURES WITH DDT (VARIOUS PROPORTIONS).

Soluble concentrate (400, 552, or 600 g/l)

(Monocrotophos +) dodine + dinocap; mevinphos; parathion-methyl; cypermethrin; parathion-methyl + sulfur.

Water miscible, soluble concentrate, technical concentrate, water soluble concentrate.

For more Formulations/Preparations (Complete) data for MONOCROTOPHOS (6 total), please visit the HSDB record page.

Use ClassificationINSECTICIDES
General Manufacturing Information · 3건

The WHO Recommended Classification of Pesticides by Hazard identifies Monocrotophos (technical grade) as Class IB: highly hazardous; Main Use: insecticide. According to the PIC /Prior Informed Consent/ Convention, export of /Monocrotophos/ can only take place with the prior informed consent of the importing Party. ...(further information can be found at: http://www.pic.int/).

Dosage rates against mites and sucking insects are 250 to 500 g/ha, against lepidopterous larvae 500-1000 g/ha.

IT IS INCOMPATIBLE WITH ALKALINE PESTICIDES.

응용 분야 · 2건

용도Monocrotophos is an organophosphorous insecticide. Monocrotophos is used mainly against cotton pests but it is also used in the protection of citrus, rice, potatoes, vegetables and other crops.

일반 설명Colorless crystals with a mild ester odor, commercial product is a reddish-brown solid. Used as a fast acting insecticide with both systemic and contact action against a wide range of pests on cotton, sugar cane, tobacco, potatoes, peanuts, tomatoes, and ornamentals. Very toxic.

상·하류 제품 정보

상류 원료

트리메틸포스파이트N-메틸-3-옥소부타나마이드

하류 제품

염화메틸

추가 설명

정의ChEBI: An alkenyl phosphate that is the 4-(methylamino)-4-oxobut-2-en-2-yl ester of dimethyl phosphate.