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Diamidafos

HCID 15643
NotesReactions
Basic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
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Basic information

CAS
1754-58-1
Standard SMILES
CNP(=O)(NC)Oc1ccccc1
InChIKey
ZKIBFASDNPOJFP-UHFFFAOYSA-N
Molecular formula
C8H13N2O2P
Average molar mass
200.17 g/mol
Monoisotopic mass
200.07146466

Overview

Diamidafos is a phosphorodiamide.

Names & identifiers

Preferred name
Diamidafos
IUPAC
N-[methylamino(phenoxy)phosphoryl]methanamine
English name
phenyl N,N'-dimethylphosphorodiamidate
Molecular formula
C8H13N2O2P
Molecular weight
200.17

Names & synonyms

Diamidafos1754-58-1DiamidfosNELLITEDiamidaphosPhenyl N,N'-dimethylphosphorodiamidateDowco 1698NX8P1GOF9O-Phenyl-N,N'-dimethyl phosphorodiamidatePhosphorodiamidic acid, N,N'-dimethyl-, phenyl esterRefChem:132610217-144-7
Show more names
Nellite.Bis(methylamido)phosphorsaeure-phenylestermethyl-[methylamino(phenoxy)phosphoryl]amineN,N'-Dimethylphosphorodiamidic acid phenyl ester
N-[methylamino(phenoxy)phosphoryl]methanamineDiamidofosDiamidafos [ANSI]Caswell No. 654BHSDB 1751Diamidafos [ANSI:ISO]EINECS 217-144-7UNII-8NX8P1GOF9

Database identifiers

CAS
1754-58-1
PubChem CID
15643
DTXSID
DTXSID6041846
ChEBI
CHEBI:82164
UNII
8NX8P1GOF9
EC Number
217-144-7
Nikkaji
J7.768B

Properties

Computed structural properties

XLogP
0.8
Topological polar surface area
50.4 Ų
Hydrogen bond donors
2
Hydrogen bond acceptors
4
Rotatable bonds
4
Heavy atoms
13
Formal charge
0
Complexity
185

Experimental & physicochemical properties

PesticidesPesticides -> Organophosphate Insecticides
OdorODORLESS
Color/Form · 2 items

WHITE CRYSTALLINE SOLID

Colorless solid

Solubility · 4 items

IN WATER 4%; SOL IN ACETONE, CHLOROFORM, METHANOL, METHYLENE CHLORIDE

INSOL IN NON-POLAR SOLVENTS

Water solubility ca. 30 g/L

Water solubility = 50,000 mg/L

Melting Point101-103 °C
Vapor Pressure · 2 items

0.000362 [mmHg]

VERY LOW

Physical DescriptionColorless or white odorless solid; [HSDB]
Other Experimental PropertiesSlightly volatile

Physicochemical properties

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

Hazard information

Hazards Summary · 1 item

A mild skin irritant; Depressed erythrocyte, plasma, and brain cholinesterase in 90 day animal feeding studies; [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]

FIFRA Requirements · 1 item

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. Pesticides for which EPA had not issued Registration Standards prior to the effective date of FIFRA, as amended in 1988, were divided into three lists based upon their potential for human exposure and other factors, with List B containing pesticides of greater concern and List D pesticides of less concern. Diamidofos is found on List B. Case No: 2155; 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): Phenyl N,N'-dimethylphosphorodiamidate; AI Status: The active ingredient is no longer contained in any registered pesticide products ... "cancelled."

Skin, Eye, and Respiratory IrritationsSlight skin irritant

Chemistry & industry

Pharmacology

Metabolism/Metabolites · 3 items

THE PHOSPHORODIAMIDATE, DIAMIDAFOS (PHENYL N,N'-DIMETHYLPHOSPHORODIAMIDATE), WAS RAPIDLY METABOLIZED BY THE RAT TO YIELD PRODUCTS OF OXIDATIVE ATTACK AT THE N-METHYL GROUP...& OF HYDROLYTIC ATTACK AT THE P-O BOND TO YIELD PHENOL (AS CONJUGATE). ANALYSIS OF MILK FOLLOWING DOSAGE...TO COW REVEALED...SAME METABOLITES.

When tobacco was treated with (14)C-diamidfos, in addition to unchanged diamidfos and unextractable material, phenyl beta-D-glucopyranoside and a glycoside of phenol were observed. In tobacco smoke, the major breakdown product was phenol.

URINE FROM SPRAGUE-DAWLEY RATS AFTER ORAL OR IV ADMIN OF DIAMIDAFOS CONTAINED PHENYL N-METHYL-PHOSPHORODIAMIDATE, PHENYL N-METHYL-N-FORMYL PHOSPHORODIAMIDATE, AND CONJUGATED PHENOL.

Absorption, Distribution and Excretion · 3 items

AFTER ADMIN OF (14)C-DIAMIDFOS TO RATS IN IV DOSES OF 1 AND 25 MG/KG, CLEARANCE OF (14)C ACTIVITY FROM PLASMA WAS BY AN APPARENT FIRST ORDER PROCESS WITH HALF-LIFE VALUES OF 2.94 AND 3.08 HR, RESPECTIVELY.

APPROX 84% OF ORAL OR IV DOSE OF DIAMIDAFOS IN SPRAGUE-DAWLEY RATS WAS EXCRETED IN URINE DURING FIRST 36 HR & APPROX 4% MORE OVER NEXT 36 HR.

/Nellite/ ... is readily absorbed from the gut ... also ... through intact skin ...

Uses & manufacturing

Uses · 6 items

Used as soil fumigant and nematocide; [HSDB]

Cancelled--no longer registered as a pesticide for use in the US; [HSDB]

Farming (Pesticides) [Category: Industry]

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

A soil fumigant and nematocide /Former use/

Nematocide /Former use/

Methods of ManufacturingPrepared by phosphorylating phenol with phosphorus oxychloride, followed by reaction with methylamine.
Formulations/Preparations...90% WATER-SOLUBLE POWDER.

Related reactions

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New reaction record

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Compound notes

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On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
Melting point
103.5 °C · 103.5°C
Boiling point
273.8 · 273.8±23.0 °C(Predicted)
Density
1.165 · 1.165±0.06 g/cm3(Predicted)
solubility
Chloroform (Slightly), Methanol (Slightly)
pka
3.43 · 3.43±0.70(Predicted)
form
solid
FDA UNII
8 NX8P1GOF9 · 8NX8P1GOF9
EPA Substance Registry System
Diamidafos (1754-58-1)
RIDADR
2783 · 2783
HazardClass
6.1 · 6.1(b)
PackingGroup
III
Hazardous Substances Data
1754 · 1754-58-1(Hazardous Substances Data)

Safety & protection

Exposure Control and Personal Protection · 1 item

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]

Disposal Methods · 1 item

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.

Toxicology

Environmental FateTERRESTRIAL FATE: LABELED NELLITE WAS APPLIED TO A FURROW IN WHICH COTTONSEED WAS PLANTED. ... SOIL EXTRACTS /SAMPLED OVER PERIOD OF 406 DAYS/ CONTAINED DIHYDROGEN PHENYLPHOSPHORIC ACID AND HYDROGEN PHENYL N-METHYLPHOSPHORAMIDATE.
Adverse EffectsOther Poison - Organophosphate
Human Toxicity Excerpts · 2 items

SLIGHT SKIN IRRITANT.

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. LOSS OF MUSCLE COORDINATION, SLURRING OF SPEECH, FASCICULATIONS & TWITCHING OF MUSCLES (PARTICULARLY OF TONGUE & EYELIDS), & GENERALIZED PROFOUND WEAKNESS. 6. MENTAL CONFUSION, DISORIENTATION & DROWSINESS. 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/

Non-Human Toxicity Excerpts · 2 items

TOXICITY TO FISH & CERTAIN OTHER AQUATIC ANIMALS IS OF RELATIVELY LOW ORDER.

/Nellite/ ... has a high oral toxicity ... Animals given 100 ppm in food for 90 days showed depressed cholinesterase levels in brain, plasma and erythrocytes.

Non-Human Toxicity Values · 3 items

LD50 Rat oral 200 mg/kg

LD50 Rabbit percutaneous <200 mg/kg

LD50 Rat oral 140 mg/kg

Regulatory information

FIFRA Requirements · 1 item

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. Pesticides for which EPA had not issued Registration Standards prior to the effective date of FIFRA, as amended in 1988, were divided into three lists based upon their potential for human exposure and other factors, with List B containing pesticides of greater concern and List D pesticides of less concern. Diamidofos is found on List B. Case No: 2155; 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): Phenyl N,N'-dimethylphosphorodiamidate; AI Status: The active ingredient is no longer contained in any registered pesticide products ... "cancelled."

Safety data

ridadr
2783
hazard_class
6.1(b)
packing_group
III
Hazardous Substances Data
1754-58-1(Hazardous Substances Data)
General Manufacturing Information
PRODUCT DISCONTINUED BY THE DOW CHEMICAL CO.
Applications · 2 items

DescriptionDiamidaphos is an obsolete organophosphate insecticide. Very little environmental fate data is available for this substance. Similarly little ecotoxicity data is available but the substance is highly toxic to birds. Diamnidaphos is moderately toxic to mammals via the oral route and is thought to be an acetylcholinesterase inhibitor.

UsesDiamidafos is a useful building block and a pesticide whose residues are sometimes found in fruits and vegetables.

Upstream & downstream products

Upstream raw materials

MethylaminePhenyl dichlorophosphate

Suppliers4 total

烟台正信新材料科技有限公司13854547682 13854547682 · [email protected]
艾吉析科技(上海)有限公司17717235263 17717235263 · [email protected]
陕西缔都医药化工有限公司029-029-81120477 17792793610 · [email protected]
XIAMEN AMITY INDUSTRY AND TRADE CO., LTD.+8618950047208 · [email protected]

Additional notes

DefinitionChEBI: Diamidafos is a phosphorodiamide.