디클로펜티온

Dichlofenthion

HCID 7328CAS 97-17-6

기본 정보

표준 SMILES
CCOP(=S)(OCC)Oc1ccc(Cl)cc1Cl
InChIKey
WGOWCPGHOCIHBW-UHFFFAOYSA-N
분자식
C10H13Cl2O3PS
평균 분자량
315.15 g/mol
단동위원소 질량
313.9700078

이름 및 식별자

우선 이름
Dichlofenthion
IUPAC
(2,4-dichlorophenoxy)-diethoxy-sulfanylidene-lambda5-phosphane
현지명
디클로펜티온
영어명
DICHLOFENTHION
분자식
C10H13Cl2O3PS
분자량
315.15

이름 및 동의어

DICHLOFENTHION97-17-6HexanemaMobilawnNemacideECP (pesticide)Tri-vc 13Nemacide VC-13v-C-13VC13 NemacideV-C 13VC 13
이름 더 보기
디클로펜티온다이클로펜티온2,4-디클로로페닐디에틸포스포로티온산포스포로티오산, O-(2,4-디클로로페닐) O,O-디에틸에스테르ECPvc13RNS3RNASE3v-c1-13V-Cl 13hexnemaNSC3130
DTXSID8040274ENT 17470Diethyl 2,4-dichlorophenyl phosphorothionateO-2,4-Dichlorophenyl O,O-diethyl phosphorothioateO-(2,4-Dichlorophenyl) O,O-Diethyl phosphorothioateNSC-52964O-(2,4-Dichlorophenyl)-O,O-diethyl phosphorothioic acidO,O-Diethyl O-(2,4-dichlorophenyl) phosphorothioate

데이터베이스 식별자

CAS
97-17-6
PubChem CID
7328
DTXSID
DTXSID8040274
ChEMBL
CHEMBL1396626
ChEBI
CHEBI:81730
UNII
64234GT8TT
EC Number
202-564-5
Nikkaji
J3.976D

물성

구조 계산 물성

XLogP
5.1
극성 표면적
59.8 Ų
수소 결합 공여자 수
0
수소 결합 수용자 수
4
회전 가능 결합 수
6
무거운 원자 수
17

실험 및 물리화학적 성질

LogPLogP= 5.14
Density1.300 @ 20 °C
Color/FormCOLORLESS LIQUID
Solubility · 3건

MISCIBLE WITH MOST ORGANIC SOLVENTS; SLIGHTLY SOLUBLE IN WATER.

SOL IN ETHANOL, ETHER, BENZENE

SOLUBILITY IN WATER: 0.245 MG/L @ 25 °C; MISCIBLE WITH KEROSENE

Boiling Point164-169 °C @ 0.1 MM HG
DecompositionWHEN HEATED TO DECOMP...EVOLVES HIGHLY TOXIC /HYDROGEN CHLORIDE/ FUMES. SOME ORGANIC DECOMP TO YIELD PHOSGENE. /CHLORIDES/

물리화학적 성질

끓는 점
0.1 · bp0.1 164-169°
밀도
20 · d20 1.300
굴절률
25 · nD25 1.5291
인화점
100 °C · 100 °C
저장 조건
0 · 0-6°C
용해도
클로로포름(약간 용해됨), 에틸아세테이트(약간 용해됨)

안전 및 규제

GHS 분류

GHS Classification · 6건

Warning

H302: Harmful if swallowed [Warning Acute toxicity, oral];H400: Very toxic to aquatic life [Warning Hazardous to the aquatic environment, acute hazard];H410: Very toxic to aquatic life with long lasting effects [Warning Hazardous to the aquatic environment, long-term hazard]

P264, P270, P273, P301+P317, P330, P391, and P501 (click each P-code to see the statement)

Danger

유해성 정보

Regulatory Information2002/2076
Other Safety InformationIMAP assessments - Phosphorothioic acid, O-(2,4-dichlorophenyl) O,O-diethyl ester: Environment tier I assessment;IMAP assessments - Phosphorothioic acid, O-(2,4-dichlorophenyl) O,O-diethyl ester: Human health tier I assessment
Hazards Summary · 1건

A cholinesterase inhibitor; [Merck Index] No significant decrease in cholinesterase activity or toxic symptoms were observed in 90 day feeding study with dogs at 0.75 mg/kg bw; [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]

Special Reports · 2건

Toxicology Review: Residue Reviews 46: 1 (1973)

Li S-Q et al; Structure-activity relationship analysis of mutagenicity of organophosphorus pesticides and their molecular mechanism. Zhongguo Yaolixue Yu Dulixue Zazhi 7 (2): 93-9 (1993). Whole structure patternization multivariant discriminant analysis was established for studying the structure-activity relationship of mutagenicity of organophosphorus pesticides, of which the 3 constituents were patternized in subtype patterns, and then 36 categories of structural patterns of OPPs were constructed.

DOT Hazard Classification · 3건

Dichlofenthion

Severe marine pollutant

Other Hazardous Reactions · 2건

...SHOCK CAN SHATTER CONTAINER, RELEASING CONTENTS. /PARATHION/

A portion of even the most flammable materials is likely to be lost by vaporization. ... The smoke from an open fire used to destroy pesticides will contain some of the poison. Burning should be attempted only in an isolated place. Inhalation of smoke must be avoided. /Pesticides/

안전 및 보호

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 · 2건

If material on fire or involved in fire: Do not extinguish fire unless flow can be stopped. Solid streams of water may be ineffective. Cool all affected containers with flooding quantities of water. Apply water from as far a distance as possible. Use "alcohol" foam, carbon dioxide or dry chemical. /Organophosphorus pesticides, liquid, NOS/

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 · 3건

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/

Disposal Methods · 4건

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.

It is stable to hydrolysis except under strongly alkaline conditions. On heating @ 175 °C for 8 hr, 42% is converted into the O,S-diethyl isomer. Recommendable method: Incineration. Peer review: Incinerate @ high temp in a unit with effluent gas scrubbing. (Peer-review conclusions of an IRPTC expert consultation (May 1985))

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/

Preventive Measures · 5건

/IT IS/ NECESSARY TO PREVENT INHALATION & SKIN CONTAMINATION. /PARATHION/

Avoid contact with...eyes...

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/

Special aircraft should preferably be used for spraying or dusting toxic organophosphorus pesticides. ... aerial spraying or dusting gives rise to clouds which spread over larger surfaces than clouds produced by ground application. Aerial spraying should therefore be carried out on windless days only. Residential areas, water supply sources, etc must be avoided. ... When aircraft approaches, signalmen /guiding the aircraft/ should leave the windward side. ... The local population should be informed about the site & time of aerial pesticide treatment. Access of unauthorized persons & especially children to the area to be treated must be ... forbidden. Warning signs should be placed at the limits of the area. Ground spraying must be carried out with compressed-air spraying equipment towed by tractors with closed cabs. /Organophosphorus pesticides/

For more Preventive Measures (Complete) data for DICHLOFENTHION (10 total), please visit the HSDB record page.

Personal Protective Equipment (PPE) · 2건

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/

독성 정보

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/

Ecotoxicity Values · 5건

LC50 Gammarus fasciatus 110 ug/L/96 hr at 15 °C, mature (95% confidence limit 80-150 ug/L). 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 Gammarus lacustris 56 ug/L/96 hr at 15 °C, mature (95% confidence limit 40-78 ug/L). 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 Pteronarcys californica 4.1 ug/L/96 hr at 15 °C, second yr class (95% confidence limit 3.4-5.0 ug/L). 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 Salmo clarki (cutthroat trout) 640 ug/L/96 hr at 13 °C, wt 1.0 g (95% confidence limit 550-740 ug/L). 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%/

For more Ecotoxicity Values (Complete) data for DICHLOFENTHION (9 total), please visit the HSDB record page.

Environmental Fate · 3건

TERRESTRIAL FATE: Based on a recommended classification scheme(1), an estimated Koc value of 15,000(SRC), determined from a measured log Kow(2) and a recommended regression-derived equation(3), indicates that dichlofenthion will be immobile in soil(SRC). Volatilization of dichlofenthion may be important from moist soil surfaces(SRC) given an estimated Henry's Law constant of 9.5X10-4 atm-cu m/mole(SRC), calculated from experimental values for vapor pressure(4) and water solubility(5). Volatilization from dry soil surfaces(SRC) is not expected, based on dichlofenthion's measured vapor pressure(4).

AQUATIC FATE: Based on a recommended classification scheme(1), an estimated Koc value of 15,000(SRC), determined from a measured log Kow(2) and a recommended regression-derived equation(1), indicates that dichlofenthion should adsorb to suspended solids and sediment in the water(SRC). Dichlofenthion may volatilize from water surfaces based on an estimated Henry's Law constant of 9.5X10-4 atm-cu m/mole(SRC), calculated from experimental values for vapor pressure(3) and water solubility(4). Estimated half-lives for a model river and model lake are 7 hours and 8 days, respectively(1,SRC). An estimated BCF value of 4700(1,SRC), from a measured log Kow(2), suggests that dichlofenthion will bioconcentrate in aquatic organisms(SRC), according to a recommended classification scheme(5).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), dichlofenthion, which has a measured vapor pressure of 5.6X10-4 mm Hg at 20 °C(2), will exist both the vapor and particulate phases in the ambient atmosphere. Vapor-phase dichlofenthion 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 4 hours(3,SRC). Particulate phase dichlofenthion may be physically removed from air by dry deposition(SRC).

Adverse EffectsOther Poison - Organophosphate
Animal ConcentrationsDichlorfenthion is included in the EPA's database of compounds identified in human biological media (tissues and body fluids)(1).
Acute Toxicity LinkChemical: DICHLOFENTHION

규제 정보

Regulatory Information2002/2076

안전 데이터

wgk
3
rtecs
TF0350000
ridadr
2783
독성
LD50 in male, female rats (mg/kg): 185, 172 orally; 576, 355 dermally (Gaines, Linder)
HS 번호
29201900
risk_code
22-50/53

화학 및 산업

약리 정보

Mechanism of Action · 5건

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/

The main feature of the toxic mechanism of organophosphorus pesticides is inhibition of the esterase enzyme activity, in particular of cholinesterase, which plays an important physiological part. Organophosphorus pesticides can also indirectly interact with the biochemical receptors of acetylcholine. /Organophosphorus pesticides/

... The serum cholinesterase activity of 14 men and 16 women at seven approximately equal intervals throughout one 24 hr day was measured. The lowest average value, ... was 92% of the mean of all values at other sampling times. The next lowest value was 98.7% of the same mean. /It was/ concluded that the small variation observed did not take the form of a regular curve but was entirely individual without correspondence to hour. /Organic phosphorus pesticides/

For more Mechanism of Action (Complete) data for DICHLOFENTHION (6 total), please visit the HSDB record page.

Metabolism/Metabolites · 5건

WHEN NEMATOCIDE WAS FED TO LAYING HENS...METABOLITE 2,4-DICHLOROPHENOL WAS FOUND IN LIVER & YOLK.

... Oxidation to the phosphate, dealkylation, and hydrolytic cleavage of the dichlorophenol moiety.

Plasma and tissue enzymes are responsible for hydrolysis /of organophosphorus compounds/ to the corresponding phosphoric and phosphonic acids. However, oxidative enzymes are also involved in the metabolism of some organophosphorus compounds. /Anticholinesterase agents/

The organophosphorus anticholinesterase agents are hydrolyzed in the body by a group of enzymes known as A-esterases or paroxonase, and by the cytochrome p-450 systems. Considerable variability exists in the human population for organophosphate metabolism by these routes. The A-esterases are found in plasma and in the hepatic endoplasmic reticulum and can hydrolyze a large number of organophosphorus compounds ... by splitting the anhydride, P-F, P-CN, or ester bond. /Anticholinesterase agents/

These chemicals are detoxified by cytochrome p450-mediated monooxygenases in the liver, but some metabolites are more toxic than parent cmpd ... Metabolites usually are detected from 12 to 48 hr postexposure. /Organophosphate cmpd/

Absorption, Distribution and Excretion · 5건

/IN CATTLE SPRAYED WITH & SHEEP & GOATS DIPPED IN SOLN OF VC-13/... NON-HYDROLYZED VC-13 RESIDUES WERE GREATEST IN FAT & FATTY TISSUES...FREE 2,4-DICHLOROPHENOL, HYDROLYSIS PRODUCT OF VC-13, OCCURRED PRIMARILY IN THE KIDNEY AND LIVER. RESIDUES /NON-HYDROLYZED/ WERE AT MAXIMUM AT 7 DAYS AFTER EXPOSURE; DECLINED GRADUALLY; & WERE ELIMINATED IN 6 WEEKS BY CATTLE AND IN 8 WEEKS BY SHEEP AND GOATS.

Percutaneous absorption is a potential danger. It is stored in and slowly released from body fat depots. As a result symptoms may be delayed hr or days after a single dose or recurrent attacks may occur. Dichlofenthion has been identified in fat biopsies, serum and urine up to 48 days after exposure.

DICHLOFENTHION HAS A HIGHER OCTANOL/WATER PARTITION COEFFICIENT THAN MOST ORGANOPHOSPHORUS INSECTICIDES, & PROLONGED COURSE OF POISONINGS.../IS/ DUE TO A SLOW RELEASE OF THE INSECTICIDE FROM ADIPOSE TISSUE RESERVOIRS.

The concn of dichlofenthion in the tissues of a man who died on the 3rd day after ingesting dichlofenthion were 19 and 0.83 ppm in serum and kidney, respectively. In a similar case the values were 174 ppm in fat, 37 ppm in bile, 4 ppm in liver, and 1.3 ppm in kidney.

For more Absorption, Distribution and Excretion (Complete) data for DICHLOFENTHION (12 total), please visit the HSDB record page.

용도 및 제조

Uses · 3건

Used as pesticide (may be restricted); [Hawley] Used as nematocide and insecticide; [Merck Index]

Farming (Pesticides) [Category: Industry]

NEMATOCIDE & INSECTICIDE

Methods of Manufacturing · 2건

PREPD FROM O,O-DIETHYLPHOSPHOROCHLORIDOTHIOATE, 2,4-DICHLOROPHENOL & SODIUM HYDROXIDE).

PRODUCED BY THE REACTION OF O,O-DIETHYL PHOSPHOROCHLORIDOTHIOATE WITH 2,4-DICHLOROPHENOL IN BUTANONE IN PRESENCE OF ANHYDROUS SODIUM CARBONATE...

Formulations/Preparations · 5건

'MOBILAWN': EC (250 & 750 G AI/L); GRANULES (100 G/KG).

V-C 13 NEMACIDE: 80% AI AND 20% EMULSIFIER.

EMULSIFIABLE CONCENTRATE

TECHNICAL PRODUCT IS OF 95-97% PURITY.

Mixed formulations: (dichlofenthion +) thiram

Use ClassificationINSECTICIDES
General Manufacturing Information · 4건

The WHO Recommended Classification of Pesticides by Hazard identifies Dichlofenthion (technical grade) as an active ingredient believed to be obsolete or discontinued for use as a pesticide.

.../IT/ WAS FIRST REPORTED AS NEMATICIDE BY MANZELLI, MA, PL DIS REPTR, 1955, 39, 400. IT WAS INTRODUCED, IN 1956, BY VIRGINIA-CAROLINA CHEMICAL CORPORATION UNDER CODE NAME 'V-C 13 NEMACIDE', & PROTECTION OF US PATENT 2,761,806. ... DICHLOROFENTHION IS NON-SYSTEMIC NEMATICIDE & SOIL INSECTICIDE RECOMMENDED FOR SOIL USE @ 16.8-280 KG AI/ACRE... RATES AGAINST SOIL INSECTS ARE AT THE LOW, & AGAINST NEMATODES @ HIGH ENDS OF THIS RANGE.

CONTROLS NON-CYST FORMING NEMATODES ON ORNAMENTALS & TURF WITHOUT DAMAGE TO PLANTS. ESTABLISHED SHRUBS SUCH AS BOXWOOD, JAPANESE HOLLY, ETC, CAN BE TREATED TO CONTROL NEMATODES WITHOUT PHYTOTOXICITY. INSECTICIDE USES INCLUDE CONTROL OF LAWN CINCH BUGS ON ST AUGUSTINE GRASS. USED FOR NEMATODE CONTROL ON AFRICAN VIOLETS.

Miscible with other emulsifiable concentrates

응용 분야

용도Nematocide, insecticide.

상·하류 제품 정보

공급사50 곳

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