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Phosphamidon

HCID 25750
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基本情報概要名称と識別子物性安全と法規制化学と産業関連反応化合物ノート
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基本情報

CAS
13171-21-6
標準SMILES
CCN(CC)C(=O)C(Cl)=C(C)OP(=O)(OC)OC
InChIKey
RGCLLPNLLBQHPF-UHFFFAOYSA-N
分子式
C10H19ClNO5P
平均分子量
299.69 g/mol
単同位体質量
299.06893702

概要

Phosphamidon is a pale yellow oily liquid with a faint odor. Used as an insecticide for citrus, cotton, and deciduous fruit and nuts. and as an acaricide. (EPA, 1998)

名称と識別子

優先名称
Phosphamidon
IUPAC
[3-chloro-4-(diethylamino)-4-oxobut-2-en-2-yl] dimethyl phosphate

名称と別名

DTXSID70211562-Chloro-3-(diethylamino)-1-methyl-3-oxo-1-propenyl dimethyl phosphateFosfamidonPhosphamidoneMerkonML 97Dimecron 100Sundaram 1975OR 1191Phosphamidon 85 WSCFoszfamidonN,N-Diethyl 2-chloro-3-dimethylphosphate crotonamide
名称をさらに表示
DTXCID201156CHEBI:388321-Chloro-diethylcarbamoyl-1-propen-2-yl dimethyl phosphate2-Chloro-2-diethylcarbamyl-1-methylvinyl-dimethyl phosphate2-Chloro-2-diethylcarbamoyl-1-methylvinyl dimethyl phosphate2-Chloro-N,N-diethyl-3-hydroxycrotonamide dimethyl phosphate7H857A6N6HDimethyl phosphate of 2-chloro-N,N-diethyl-3-hydroxycrotonamide

データベース識別子

CAS
13171-21-6、297-99-4
PubChem CID
25750
DTXSID
DTXSID7021156
ChEMBL
CHEMBL3182713
EC Number
236-116-5

物性

構造計算による物性

XLogP
1.3
極性表面積
65.1 Ų
水素結合供与体数
0
水素結合受容体数
5
回転可能結合数
7
重原子数
18
形式電荷
0
複雑度
359

実験および物理化学的性質

Pesticides · 4 件

Acaricides, Insecticides

Active substance -> EU Pesticides database: Not approved

Pesticides -> Organophosphate Insecticides

Pesticide (Phosphamidon) -> USDA PDB

LogP · 2 件

0.8

1.34

OdorFAINT ODOR
Density · 4 件

1.2132 at 77 °F (EPA, 1998) - Denser than water; will sink

1.2132 @ 25 °C/4 °C

Relative density (water = 1): 1.2

1.21 @25 °C

ViscosityDENSITY: 1.22 @ 20 °C/4 °C; VISCOSITY: 70 CENTIPOISES @ 25 °C /TECHNICAL PRODUCT/
Color/Form · 3 件

Pale-yellow liquid

COLORLESS LIQUID

Oil

Solubility · 4 件

greater than or equal to 100 mg/mL at 72 °F (NTP, 1992)

Miscible with most org solvents except saturated hydrocarbons; 1 g dissolves in about 30 g hexane

In water, miscible @ 25 °C

Solubility in water: miscible

CorrosivityCorrosive to iron, tin, aluminum; non-corrosive to polyethylene
Flash Pointgreater than 200 °F (NTP, 1992)
Boiling Point · 4 件

324 °F at 1.5 mmHg (EPA, 1998)

120 °C @ 0.001 mm Hg; 162 °C 1.5 mm Hg

at 0.2kPa: 162 °C

350 °C @760 [mm Hg]

Decomposition · 3 件

When heated to decomposition it emits toxic fumes of /phosphorous and nitric oxides/.

Hydrolyzed by alkali with t1/2 of 14 day at pH 7 and 23 °C; 2.2 day at pH 10.

Produces highly toxic phosphorus oxides and chlorides fumes above 160 °C.

Melting Point · 4 件

-49 °F (EPA, 1998)

-45 °C

-45 °C

-45 °C

安全と法規制

安全情報は参考情報です。供給元の安全データシート(SDS)、適用法令、専門家による評価に代わるものではありません。

GHS分類

GHS Classification · 6 件

Danger

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

P203, P262, P264, P270, P273, P280, P301+P316, P302+P352, P316, P318, 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]

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)

危険有害性情報

Regulatory Information · 2 件

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.)

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

(Non-Specific -- Organophosphorus Pesticide, Liquid, n.o.s.) Container may explode in heat of fire. Heat above 320F may cause decomposition and evolution of highly toxic fumes of phosphorus oxides and chlorides. Hydrolyzes in alkali. Stable in neutral and acid media. Hydrolyzes in alkali. (EPA, 1998)

Liquid formulations containing organic solvents may be flammable. Gives off irritating or toxic fumes (or gases) in a fire.

Health HazardsThis material is extremely toxic; the probable oral lethal dose for humans is 5-50 mg/kg, or between 7 drops and 1 teaspoonful for a 150-lb person. It is a cholinesterase inhibitor. (EPA, 1998)
Hazards Summary · 1 件

An eye irritant; Can be absorbed through skin; A cholinesterase inhibitor that may cause CNS effects resulting in convulsions and respiratory depression; [ICSC] Gamma-Chlorophosphamidon, present as an impurity at a level of 1-2% in the technical product, is approximately 20 times more potent as a human cholinesterase inhibitor; In a human test involving unprotected exposure from aircraft spraying in a paddy field, volunteers experienced immediate eye irritation and depression of plasma cholinesterase by as much as 50%; No evidence of delayed neurotoxicity in hens; [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]

Reactive GroupAmides and Imides
EC ClassificationSymbol: T+, N; R: 24-28-68-50/53; S: (1/2)-23-36/37-45-60-61
UN ClassificationUN Hazard Class: 6.1; UN Pack Group: II
Special ReportsDHEW/NCI; Bioassay of Phosphamidon for Possible Carcinogenicity (1979) Technical Rpt Series No. 16 DHEW Pub No. (NIH) 79-816
FIFRA Requirements · 4 件

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. Phosphamiidon 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: 0157; Pesticide type: Insecticide; Registration Standard Date: 12/87; Case Status: The last registered pesticide products containing this pesticide were voluntarily cancelled by their registrants while EPA was developing the Reregistration Eligibility Decision (RED) document.; Active ingredient (AI): Phosphamiidon; AI Status: The active ingredient is no longer contained in any registered pesticide products ... "cancelled."

Tolerances (expressed as phosphamidon) for residues of the insecticide phosphamidon (2-chloro-2-diethylcarbamoyl-1-methylvinyl diemthyl phosphate) including all of its related cholinesterase-inhibiting compounds in or on raw agricultural commodities are established as follows: apples (Expiration/Revocation Date 12/31/02)

Classified for restricted use and limited to use by or under the direct supervision of a certified applicator. Formulation: Liquid formulations 75% and greater; Use Pattern: Rice; Classification: Resticted; Criteria Influencing Restriction: Acute dermal toxicity. Residue effects on mammalian species. Residue effects on avian species.

Classified for restricted use and limited to use by or under the direct supervision of a certified applicator. Formulation: Dust formulations 1.5% and greater; Use Pattern: All uses; C Classification: Restricted; Criteria Influencing Restriction: Acute dermal toxicity. Residue effects on mammalian species. Residue effects on avian species.

Reactivity ProfilePHOSPHAMIDON is corrosive to iron, tin and aluminum. Incompatible with alkaline preparations and should not be mixed with copper oxychloride, captan, folpet or sulfur. (NTP, 1992)

安全と保護具

Fire Fighting · 2 件

(Non-Specific -- Organophosphorus Pesticide, Liquid, n.o.s.) Stay upwind; keep out of low areas. Move containers from fire area if you can do it without risk. Fight fire from maximum distance. Dike fire control water for later disposal; do not scatter the material.

In case of fire in the surroundings, use appropriate extinguishing media.

First Aid Measures · 4 件

Fresh air, rest. Artificial respiration may be needed. 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.

Rinse mouth. Induce vomiting (ONLY IN CONSCIOUS PERSONS!). Give a slurry of activated charcoal in water to drink. Refer immediately for medical attention.

First AidNote: Phosphamidon is a cholinesterase inhibitor.
Safe StorageStore in an area without drain or sewer access. Well closed. Keep in a well-ventilated room. Separated from bases and food and feedstuffs.
Exposure Control and Personal Protection · 1 件

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 · 3 件

If material on fire or involved in fire: Do not extinguish fire unless flow can be stopped. Use water in flooding quantities as fog. 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, dry chemical or carbon dioxide. /Organophosphorus pesticides, liquid, flammable, toxic; Organophosphorus pesticides, liquid, toxic/

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

Fire Service personnel should extinguish fires with alcohol-resistant foam, water spray, or dry powder.

Storage Conditions · 2 件

You should store this material under ambient temperatures.

It... is packed in polyethylene containers.

Cleanup Methods · 4 件

Environmental considerations: Air spill: Apply water spray or mist to knock down vapors. /Organophosphorus pesticides, liquid, flammable, toxic; Organophosphorus pesticides, liquid, toxic; Organophosphorus pesticides, solid, toxic/

Environmental considerations: Water spill: Use natural barriers or oil spill control booms to limit spill travel. Remove trapped material with suction hoses. /Organophosphorus pesticides, liquid, flammable, toxic; Organophosphorus pesticides, liquid, toxic; Organophosphorus pesticides, solid, toxic/

Environmental considerations: Land spill: Dig a pit, pond, lagoon, holding area to contain liquid or solid material. /SRP: If time permits, pits, ponds, lagoons, soak holes, or holding areas should be sealed with an impermeable flexible membrane liner./ Dike surface flow using soil, sand bags, foamed polyurethane, or foamed concrete. Absorb bulk liquid with fly ash, cement powder, or commercial sorbents. /Organophosphorus pesticides, liquid, flammable, toxic; Organophosphorus pesticides, liquid, toxic; Organophosphorus pesticides, solid, toxic/

Collect leaking and spilled liquid in sealable containers as far as possible. Absorb remaining liquid in sand or inert absorbent and remove to safe place. Do NOT wash away into sewer. (Extra personal protection: complete protective clothing including self-contained breathing apparatus).

Nonfire Spill ResponseCaution : Explosion potential is high. Containers may explode in heat of fire. Highly toxic phosphorus oxides and chlorides may be emitted when phosphamidon is heated to decomposition. Avoid sources of extreme heat.
Disposal Methods · 3 件

SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations.

Hydrolysis...: Treat phosphamidon by alkali, then mix the product with a portion of soil rich in organic matter. ...Recommendable method: Incineration. Peer-review: Incineration in a unit with effluent gas scrubbing is recommendable for large amounts. (Peer-review conclusions of an IRPTC expert consultation (May 1985))

Hydrolysis: Hydrolysis products are pH dependent. Acidic hydrolysis yields alpha-chloroacetoacetic acid diethylamide. The amide can subsequently degrade to diethyl amine, carbon dioxide and chloroacetone in strong acid or with heating. A different series of products have been identified for the alkaline hydrolysis. Although the diethyl amide of alpha-chloroacetoacetic acid appears to initially form, it very rapidly hydrolyzes, even in weak alkaline soln, and yields chloride and the diethylamide of alpha-hydroxyacetoacetic acid. In strong alkali this amide can slowly hydrolyze to yield acetic acid and glycolic acid diethylamide. The product, glycolic acid diethylamide, is stable in base. The hydrolysis products are non-toxic and rapidly assimilated into natural constituents. Empty containers should be rinsed by an alkaline soln.

Spillage Disposal · 1 件

Personal protection: chemical protection suit including self-contained breathing apparatus. Do NOT let this chemical enter the environment. Collect leaking and spilled liquid in sealable non-metallic containers as far as possible. Absorb remaining liquid in sand or inert absorbent. Then store and dispose of according to local regulations.

Preventive Measures · 5 件

Poisonous if swallowed, inhaled, or absorbed through skin. ... Do not get in eyes, on skin or clothing. Do not breathe mist. ... Wash thoroughly after handling. Do not drink any alcoholic beverage before or during spraying since alcohol promotes absorption of organic phosphates.

If material not on fire and not involved in fire: Keep sparks, flames, and other sources of ignition away. Keep material out of water sources and sewers. /Organophosphorus pesticides, solid, toxic

If material not on fire and not involved in fire: Keep sparks, flames, and other sources of ignition away. Keep material out of water sources and sewers. Build dikes to contain flow as necessary. Attempt to stop leak if without undue personnel hazard. Use water spray to knock-down vapors. /Organophosphorus pesticides, liquid, toxic/

If material not on fire and not involved in fire: Keep sparks, flames, and other sources of ignition away. Keep material out of water sources and sewers. Build dikes to contain flow as necessary. Use water spray to knock-down vapors. /Organophosphorus pesticides, liquid, flammable, toxic/

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

毒性情報

Interactions · 4 件

...Phosphamidon and dimethylvinphos, have their acute toxicities reduced by phenobarbital pre-treatment.

Vitamin C, when admin concurrently with a pesticide ... phosphamidon ... could significantly decr the frequency of pesticide induced clastogenic and mitosis disruptive changes in the bone marrow cells of young Swiss Albino mice. Of these three doses (10, 20 or 40 mg/kg/bw) of the vitamin, the one which is double the human therapeutic dose (20 mg/kg/bw/day) was the most effective as an antimutagen to be followed by 40 mg and 10 mg. None of these doses of vitamin C showed any genotoxicity of their own for the parameters studied here.

Because different classes of enzymes may be inhibited, the effects of organophosphorus pesticide poisoning may be complex and potentially at least could involve interactions with drugs as well as with other pesticides or chemicals. Potentiation may also involve solvents or other components of formulated pesticides. Certain drugs such as phenothiazines, antihistamines, CNS depressants, barbiturates, xanthines (theophylline), aminoglycosides and parasympathomimetic agents are to be avoided because of increased toxicity.

/When citiolone was administered with phosphamidon/... significant depletion was observed in the glutathione-S-transferase activity as well as in the level of total and non-protein bound sulfhydryl groups in various CNS regions of phosphamidon intoxicated rats. When citiolone was administered alone, there was a remarkable elevation in glutathione-S-transferase activity. However, significant protection against glutathione-S-transferase inhibition was observed when phosphamidon and citiolone were administered simultaneously.

Ecotoxicity Values · 5 件

LD50 ANAS PLATYRHYNCHOS (MALLARD) ORAL 3.05 MG/KG, 3 MO OLD FEMALES (95% CONFIDENCE LIMIT 2.91-5.00) /SAMPLE PURITY 80%/

LD50 PERDIX PERDIX (PARTRIDGE) ORAL 9.7 MG/KG, 3 MO OLD FEMALES & MALES (95% CONFIDENCE LIMIT 8.3-11.3)

LD50 ZENAIDA MACROURA (MOURNING DOVE) ORAL MALES AND FEMALES 2.0-4.0 MG/KG

LD50 ZENAIDA ASIATICA (WHITE WINGED DOVE) ORAL, ADULT MALE AND FEMALE, 2.93 MG/KG (95% CONFIDENCE LIMIT 2.44-3.66 MG/KG) /SAMPLE PURITY 80%/

For more Ecotoxicity Values (Complete) data for PHOSPHAMIDON (15 total), please visit the HSDB record page.

Environmental Fate · 3 件

TERRESTRIAL FATE: Based on a a soil thin layer chromatography study, retardation factors (Rf) of 0.91-0.92 in a silt loam, silt loam, and a fine sandy loam(1), indicate that phosphamidon has very high mobility in soil(SRC). Volatilization of phosphamidon from moist soil surfaces is not expected to be an important fate process(2) given an estimated Henry's Law constant of 1.5X10-12 atm-cu m/mole(SRC), using a fragment constant estimation method(3). Phosphamidon is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 1.65X10-5 mm Hg(4). Half-lives in loam, loamy sand, and sand of approximately 6, 3, and <3 days, respectively(5), indicate that biodegradation of phosphamidon may be an important environmental fate process in soil.

AQUATIC FATE: Based on a a soil thin layer chromatography study, retardation factors (Rf) of 0.91-0.92 in a silt loam, silt loam, and a fine sandy loam(1) indicate that phosphamidon is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(2) based upon an estimated Henry's Law constant of 1.5X10-12 atm-cu m/mole(SRC), developed using a fragment constant estimation method(3). According to a classification scheme(4), a BCF of <1(5) suggests the potential for bioconcentration in aquatic organisms is low(SRC). Phosphamidon's hydrolysis half-lives at 23 °C are 74 days, 13.8 days, and 2.2 days at pH 4, 7, and 10, respectively(6).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), phosphamidon, which has a vapor pressure of 1.65X10-5 mm Hg at 25 °C(2), will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase phosphamidon 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 10.5 hrs(SRC), calculated from its rate constant of 3.7X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Particulate-phase phosphamidon may be removed from the air by wet and dry deposition(SRC). The rate constant for the vapor-phase reaction of phosphamidon with ozone has been estimated as 1.6X10-16 cu cm/molecule-sec at 25 °C(SRC), derived using a structure estimation method(1); this corresponds to an atmospheric half-life of about 7 days at an atmospheric concentration of 7X10+11 ozone molecules per cu cm(4).

Food Survey Values · 1 件

In a pesticide screening study of 81 varieties of domestic and imported produce (6970 samples), no residues of phosphamidon were found above the detection limit of 0.50 ppm(1). According to FDAs Total Diet Study, April 1982-April 1984, the dietary intake of phosphamidon for each of seven population groups of different sex and age ranging from toddlers to seniors was <0.1 ng/kg body weight/day(2). According to FDA's Total Diet Study, phosphamidon residues are not present in food items consumed by infants(2). Phosphamidon is destroyed by heat >160 °C(3). After 1 hr of cooking, residue levels in apples and pears decreased by 80%(3). In a 1992-1993 FDA survey of domestic and imported pears and tomatoes, phosphamidon was not detected in any of the 710 domestic and 949 imported pear samples tested; neither was it detected in the 1219 domestic and 144 imported tomato samples tested(4).

Adverse EffectsOther Poison - Organophosphate
Exposure RoutesThe substance can be absorbed into the body by inhalation of its aerosol, through the skin and by ingestion.
Milk ConcentrationsMany of the organophosphorus insecticides are excreted in the milk ... /Organophosphorus insecticides/
Ecotoxicity Excerpts · 5 件

/AQUATIC SPECIES/ /Phosphamidon/ may be hazardous to the environment; special attention should be given to aquatic organisms, birds and honey bees.

/AQUATIC SPECIES/ Glycogen levels were decreased and lactic acid levels increased in the tissues (hepatopancreas, foot, and mantle) of mussels exposed to phosphamidon (8 ppm for 48 hr). /Phosphamidon/ decreased oxidative metabolism in the tissues of the mussels. Consequently, the mussels switch over to anaerobiasis as an adaptive measure to combat the induced toxicity.

/AQUATIC SPECIES/ Dimecron (2.50-6.00 ppm), produced elevated activity of fructose 1,6-diphosphate aldolase of liver, brain and gill tissues in Clarias batrachus exposed for 24-96 hr. The toxic conditions produced by the pesticide ultimately caused the death of the fish due to the failure of the respiratory center of the brain. The breakdown of proteins and the diabetic condition caused by the pesticides possibly increased aldolase activity.

/AQUATIC SPECIES /Phosphamidon is/... slightly toxic to fish.

For more Ecotoxicity Excerpts (Complete) data for PHOSPHAMIDON (12 total), please visit the HSDB record page.

Plant Concentrations · 1 件

The concn of phosphamidon on treated foliage 18-24 hr after spraying in an apple orchard was 20 ppm(1). Foliage in a grapefruit orchard contained 150 ppm phosphamidon 23 hours after spraying(1). Phosphamidon is rapidly absorbed and metabolized in plants(3). Reported initial half-lives are of the order of 1-2 days(1,2,3). Degradation then proceeds more slowly with residues decreasing to the 0.5 ppm level or less in about 1 week in leafy plants and 2-3 weeks in fruit after normal application(1,2,3).

Animal ConcentrationsPhosphamidon is rapidly metabolized in animals(1) and therefore residues should not be present in animals unless recently exposed.
Signs and Symptoms · 4 件

Sweating. Muscle twitching. Pupillary constriction, muscle cramp, excessive salivation. Diarrhoea. Dizziness. Laboured breathing. Vomiting. Convulsions. Unconsciousness. Symptoms may be delayed.

MAY BE ABSORBED! Further see Inhalation.

Redness. Pain.

Abdominal cramps. Further see Inhalation.

Acute Toxicity LinkChemical: PHOSPHAMIDON

法規制情報

FIFRA Requirements · 4 件

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. Phosphamiidon 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: 0157; Pesticide type: Insecticide; Registration Standard Date: 12/87; Case Status: The last registered pesticide products containing this pesticide were voluntarily cancelled by their registrants while EPA was developing the Reregistration Eligibility Decision (RED) document.; Active ingredient (AI): Phosphamiidon; AI Status: The active ingredient is no longer contained in any registered pesticide products ... "cancelled."

Tolerances (expressed as phosphamidon) for residues of the insecticide phosphamidon (2-chloro-2-diethylcarbamoyl-1-methylvinyl diemthyl phosphate) including all of its related cholinesterase-inhibiting compounds in or on raw agricultural commodities are established as follows: apples (Expiration/Revocation Date 12/31/02)

Classified for restricted use and limited to use by or under the direct supervision of a certified applicator. Formulation: Liquid formulations 75% and greater; Use Pattern: Rice; Classification: Resticted; Criteria Influencing Restriction: Acute dermal toxicity. Residue effects on mammalian species. Residue effects on avian species.

Classified for restricted use and limited to use by or under the direct supervision of a certified applicator. Formulation: Dust formulations 1.5% and greater; Use Pattern: All uses; C Classification: Restricted; Criteria Influencing Restriction: Acute dermal toxicity. Residue effects on mammalian species. Residue effects on avian species.

CERCLA Reportable Quantities · 1 件

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. Phosphamidon is an extremely hazardous substance (EHS) subject to reporting requirements when stored in amounts in excess of its threshold planning quantity (TPQ) of 100 lbs.

化学と産業

薬理情報

Mechanism of Action · 2 件

Organophosphorus pesticides exert their acute effects by inhibiting acetylcholinesterase in the nervous system with subsequent accumulation of toxic levels of acetylcholine. They may also inhibit butylcholinesterases as well as other esterase. The function of butylcholinesterases is unknown, but its inhibition can provide an indication of exposure to an organophosphate. In many cases, the organophosphorylated enzyme is fairly stable, so that recovery from intoxication may be slow. Reactivation of inhibited enzyme may occur spontaneously, the rates of reactivation depending on the tissue as well as on the chemical group attached to the enzyme. Higher doses of oximes failed to alter the reactivation of in vitro human AchE inhibited by organophosphorus compunds.

Cholinesterase inhibitor.

Metabolism/Metabolites · 5 件

Desethylphosphamidon was present in the urine of treated.../lactating goats/ both phosphamidon amide and dechlorophosphamidon amide occurred in the urine and milk...alpha-chloro-nn-diethylacetoacetamide was detected in urine and in milk.

After ip injection of cis or trans (32)P-phosphamidon in male white rats... about 60% of dose...was recovered within 24 hr after injection, most from urine. Hydrolytic products were almost entirely dimethyl phosphate, with small amount of phosphoric acid and o-demethyl phosphamidon. After foliar treatment of cotton, phosphamidon, o-demethyl phosphamidon, n-desethyl phosphamidon, hydroxyethyl phosphamidon, and dimethyl phosphate were detected externally. Internally, orthophosphate and an unknown were observed in addition to the foregoing compound. In fifth-instar tobacco budworms and bollworms, metabolism of the two isomers was similar. After injection of labeled phosphamidon.../phosphamidon, O-demethyl phosphamidon, hydroxyethyl phosphamidon, n-desethyl phosphamidon, phosphoric acid/ were observed in internal extracts /and excreta/.

Desethyl phosphamidon...alpha-chloroacetoacetic acid diethylamide, alpha-chloroacetoacetic acid ethylamide, dimethyl phosphoric acid, and unchanged phosphamidon were isolated from bean plants treated with (14)C-labeled phosphamidon. ...Metabolism of phosphamidon is unusual in that facile deethylation of the diethylamide moiety occurs with no demethylation at one of the methoxy groups. Environmental factors such as temperature and, to a lesser extent, light influence plant metabolism of phosphamidon to desethyl phosphamidon with increased rates at higher temperatures.

Rats received (32)P- and/or (14)C-labeled phosphamidon by stomach tube. .../Among metabolites found were/ vinyl hydroxyphosphamidon amide...and two compound containing only the carbon label but not further identified. Rat and rabbit liver homogenates metabolized phosphamidon... /des-n-ethyl phosphamidon and phosphamidon amide/ were found in small quantities but the hydroxy compound were not detected... .

For more Metabolism/Metabolites (Complete) data for PHOSPHAMIDON (6 total), please visit the HSDB record page.

MeSH Pharmacological Classification · 2 件

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.

Absorption, Distribution and Excretion · 5 件

The main eliminative route for phosphamidon...in rats and lactating goats was via kidneys, but small amount of several metabolites were secreted into milk of lactating goats. Only traces of unchanged /phosphamidon/ were present amongst excretory products. Desethylphosphamidon was present in urine of treated animals, whereas both phosphamidon amide and dechlorophosphamidon amide occurred in urine and milk of lactating goats. ...alpha-Chloro-nn-diethylacetoacetamide was detected in urine and in milk.

After ip injection of cis or trans phosphamidon-(32)P in male white rats, excreta was collected... About 60% of dose--either isomer--was recovered within 24 hr...most from urine... .

Phosphamidon is a systemic insecticide rapidly absorbed by the plant... In plants 50% loss occurs in about 2 days.

Early appearance of symptoms and steepness of acute dose-response curves (increased dosage levels produced disproportionately large increase in response) indicate that phosphamidon is rapidly and thoroughly taken up from GI tracts of birds.

Phosphamidon is absorbed by the respiratory and gastrointestinal tracts as well as by the skin. ...Experimental animal studies have shown that most of a radiolabelled doses of organophosphorus pesticides is rapidly excreted in expired air, urine, and feces.

用途と製造

Uses · 6 件

Used as systemic insecticide for deciduous fruits and nuts, cotton, rice, cereals, potatoes, soy beans, and other crops; [HSDB] Used as acaricide; [CAMEO]

Cancelled--no longer registered as a pesticide for use in the US; [HSDB] Banned in the EU for use as a biocide and agricultural insecticide; [eChemPortal: ESIS]

Farming (Pesticides) [Category: Industry]

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

For phosphamidon (USEPA/OPP Pesticide Code: 018201) there are 0 labels match. /SRP: Not registered for current use in the U.S., but approved pesticide uses may change periodically and so federal, state and local authorities must be consulted for currently approved uses./

INSECTICIDE FOR CITRUS AND COTTON CROPS, DECIDUOUS FRUIT & NUT CROPS

ImpuritiesIn technical preparations of phosphamidon, gamma-chlorophosphamidon is present at a level of one to two percent of the total product.
U.S. Exports · 2 件

(1976) No Data

(1978) No Data

U.S. Imports · 2 件

(1976) No Data

(1978) No Data

U.S. Production · 2 件

(1976) NOT PRODUCED COMMERCIALLY IN US

(1978) 1.36X10+8 GRAMS (CONSUMPTION, ESTIMATE)

Consumption PatternsINSECTICIDE FOR CITRUS, 33%; INSECTICIDE FOR COTTON, 33%; INSECTICIDE FOR DECIDUOUS FRUITS AND NUTS, 33% (1978)
Methods of Manufacturing · 2 件

Phosphamidon is produced by reaction of trimethylphosphite with alpha,alpha-dichloroacetic acid diethylamide.

Produced by reacting trimethyl phosphite in chlorobenzene with 2,2-dichloro-N,N-diethyl-3-oxobutyramide, which is prepared from sulfuryl chloride and N,N-diethyl-3-oxobutyramide...

Formulations/Preparations · 3 件

LIQUID, SOLUBLE CONCENTRATES, ULV FOR WATERLESS SPRAYING.

TECHNICAL PRODUCT IS OF 92% PURITY; DIMERCRON 20 (200 G/L), DIMERCRON 50, DIMERCROM 100 AND DIMERCRON ULVAIR 250

Main brand names/Trade names: Apamidon, Ciba 570, C-570, D-Cron, Dimecron, Dixon, ENT 25,515, Famfos, Merkon, ML-97, Or-1,911, Phosphamidone, Phosron, Pillarcron, Sundaram 1975 , Swat, Umecron.

Use ClassificationINSECTICIDES
General Manufacturing Information · 5 件

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

Phosphamidon is compatible with all except highly alkaline pesticides, though for an unknown reason, its biological activity is reduced by copper oxychloride.

Patents: ...British patent 829576; Belgian patent 552284; US patent 2908605; Phosphamidon exists as a mixture of 70% (z)-isomer (beta-isomer) and 30% (e)-isomer (alpha-isomer)... the (z)-isomer has the greater insecticidal activity.

NOT PRODUCED COMMERCIALLY IN US

Status: Cancelled ... RED/ Voluntary cancellation 9/96

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