Pyrazophos
Basic information
- CAS
13457-18-6- Standard SMILES
CCOC(=O)c1cn2nc(OP(=S)(OCC)OCC)cc2nc1C- InChIKey
JOOMJVFZQRQWKR-UHFFFAOYSA-N- Molecular formula
- C14H20N3O5PS
- Average molar mass
- 373.37 g/mol
- Monoisotopic mass
- 373.08612892
Overview
Pyrazophos is a member of the class of pyrazolopyrimidines that is the ethyl ester of 2-[(diethoxyphosphorothioyl)oxy]-5-methylpyrazolo[1,5-a]pyrimidine-6-carboxylic acid. A profungicide (by hydrolysis of the thionophosphate group to afford the corresponding 2-hydroxypyrazolopyrimidine fungicide), it is used to control Erysiphe, Helminthosporium and Rhynchospium in cereals. It has a role as a profungicide, an insecticide, a phospholipid biosynthesis inhibitor and an antifungal agrochemical. It is an ethyl ester, an organic thiophosphate and a pyrazolopyrimidine. It is functionally related to an ethyl 2-hydroxy-5-methylpyrazolo[1,5-a]pyrimidine-6-carboxylate.
Names & identifiers
- Preferred name
- Pyrazophos
- IUPAC
- ethyl 2-diethoxyphosphinothioyloxy-5-methylpyrazolo[1,5-a]pyrimidine-6-carboxylate
- English name
- Pyrazophos
- Molecular formula
- C14H20N3O5PS
- Molecular weight
- 373.36
Names & synonyms
PYRAZOPHOS13457-18-6CuramilAfuganDTXSID7042352BEG0A8I17DNSC-232671Ethyl 2-((diethoxyphosphinothioyl)oxy)-5-methylpyrazolo(1,5-a)pyrimidine-6-carboxylateHOE-2873DTXCID5022352CHEBI:81942O,O-Diethyl O-(5-methyl-6-(ethoxycarbonyl)-pyrazolo-(1,5-a)-pyrimid-2-yl)-thionophosphate
Show more names
hoe2873Siganexcarbonyl-AFUGAN(R)PYRAZOFOSHOE 02873
O-6-Ethoxycarbonyl-5-methylpyrazolo(1,5-a)pyrimidin-2-yl O,O-diethyl phosphorothioateEthyl 2-[(diethoxyphosphinothioyl)oxy]-5-methylpyrazolo[1,5-a]pyrimidine-6-carboxylateO-6-ethoxycarbonyl-5-methylpyrazolo[1,5-a]pyrimidin-2-yl O,O-diethyl phosphorothioateRefChem:177471236-656-1MissileHoechst 2873HOE 2873
Database identifiers
- CAS
13457-18-6- PubChem CID
- 26033
- DTXSID
DTXSID7042352
Properties
Computed structural properties
- XLogP
- 3.1
- Topological polar surface area
- 116 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 8
- Rotatable bonds
- 9
- Heavy atoms
- 24
- Formal charge
- 0
- Complexity
- 473
Experimental & physicochemical properties
SpringerMaterials PropertiesFusion temperature
Pesticides
Fungicides
Active substance -> EU Pesticides database: Not approved
Pesticide (Pyrazophos) -> USDA PDB
LogP3.8
Ionization Efficiency
Positive
2.94
2.7
Agilent XCT
Electrospray ionization
formic acid (5.3nM)
Collision Cross Section192.5 Ų [M+H]+ [CCS Type: DT; Buffer gas: N2; Ionization: APCI+; Dataset: TOXCAST; Source Identifier: DTXSID7042352]
Physicochemical properties
- Melting point
- 51 ℃ · 51℃
- Density
- 1.38 · 1.38±0.1 g/cm3(Predicted)
- vapor pressure
- 2.2 x · 2.2 x 10-4 Pa (50 °C)
- storage temp.
- 4 °C · APPROX 4°C
- pka
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Warning
H302: Harmful if swallowed [Warning Acute toxicity, oral]
P261, P264, P270, P271, P273, P301+P317, P304+P340, P317, P330, P391, and P501 (click each P-code to see the statement)
Danger
H301 (92.9%): Toxic if swallowed [Danger Acute toxicity, oral]
P261, P264, P270, P271, P273, P301+P316, P304+P340, P317, P321, P330, P391, P405, and P501 (click each P-code to see the statement)
Hazard information
Regulatory Information
00/233/EC
Pyrazophos: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.
Other Safety InformationIMAP assessments - Pyrazolo[1,5-a]pyrimidine-6-carboxylic acid, 2-[(diethoxyphosphinothioyl)oxy]-5-methyl-, ethyl ester: Human health tier I assessment
DOT Hazard Classification
Pyrazophos
Severe marine pollutant
Hazard Classes and Categories
Acute Tox. 3 (92.9%)
Acute toxicity - category 4
Acute toxicity (Oral) - Category 3
Acute Tox. 4 *
Safety data
- PPE
- dust mask type N95 (US), Eyeshields, Faceshields, Gloves
- wgk
- 3
- rtecs
- TF2035000
- ridadr
- 2783
- Toxicity
- LD50 in rats, marmots, rabbits (mg/kg): 140, 184, 435 orally (Smit)
Chemistry & industry
Applications
UsesPyrazophos is an anticholinesterase pesticide used on fruits and vegetables and can be determined by gas chromatography/mass spectrometry and liquid chromatography with fluorescence detection.
UsesFungicide.
UsesPyrazophos is a systemic fungicide that provides both protective and curative control of various fungal diseases such as powdery mildew (Podosphaera) on apples, stone fruits, bush fruits and strawberries, Erysiphe in cucurbits and tomatoes, Uncinula on vines and leaf blotch (Rhynchosporium) in cereals.
Additional notes
DefinitionChEBI: A member of the class of pyrazolopyrimidines that is the ethyl ester of 2-[(diethoxyphosphorothioyl)oxy]-5-methylpyrazolo[1,5-a]pyrimidine-6-carboxylic acid. A fungicide used to control Erysiphe, Helminthosporium and ital>Rhynchospium in cereals.
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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