ChemicalBook CAS DataBase List 13457-18-6

13457-18-6

Name	PYRAZOPHOS
CAS	13457-18-6
EINECS(EC#)	236-656-1
Molecular Formula	C14H20N3O5PS
MDL Number	MFCD00055494
Molecular Weight	373.36
MOL File	13457-18-6.mol

Synonyms

AFUGAN Curamil hoe2873 Missile Siganex HOE 2873 carbonyl- AFUGAN(R) PYRAZOFOS HOE 02873 Afugan(TM) ophosphate NSC 232671 PYRAZOPHOS Hoechst 2873 Afugan powder Pyrazophos 0.2 PYRAZOPHOS STANDARD PYRAZOPHOS, 100MG, NEAT pyrazophos (bsi,iso)afugan PYRAZOPHOS PESTANAL, 250 MG Pyrazophos Solution, 100ppm Pyrazophos @100 μg/mL in MeOH Pyrazophos 100mg [13457-18-6] Pyrazophos powder(content>55%) l)pyrazolo(1,5-a)pyrimidin-2-ol Pyrazophos emulsion(content>15%) Pyrazophos@1000 μg/mL in Acetone Pyrazophos Solution in Methanol, 100μg/mL phosphorothioicacid,o,o-diethylester,o-esterwith(6-ethoxycarbonyl-5-methy Diethyl 6-carbethoxy-5-methylpyrazolo[1,5-a]pyrimidin-2-yl phosphorothioate pyrazolo-(1,5a)pyrimidine,2-(o,o-diethyl-thionophosphoryl)-5-methyl-6-ethoxy 2-(o,o-diethyl-thionophosphoryl)-5-methyl-6-carbethoxy-pyrazolo-(1,5a)pyrimi ethyl2-((diethoxyphosphinothioyl)oxy)-5-methylpyrazolo(1,5-a)pyrimidine-6-ca o,o-diethyl-o-(5-methyl-6-ethoxy-carbonyl-pyrazolo(1.5-a)pyrimid-2-yl)-thion 2-(O,O-Diethyl thionophosphoryl)-5-methyl-6-carbethoxy-pyrazolo(1,5a)pyrimidin 2-(O,O-Diethyl-thionophosphoryl)-5-methyl-6-carbethoxy-pyrazolo-(1,5-a)pyrimidine ETHYL-2-DIETHOXYPHOSPHINOTHIOYLOXY-5-METHYLPYRAZOLO[1,5-A]-PYRIMIDINE-6-CARBOXYLATE Pyrazolo(1,5a)pyrimidine, 2-(O,O-diethyl thionophosphoryl)-5-methyl-6-ethoxycarbonyl- O,O-Diethyl-o-[5-methyl-6-ethoxycarbonylpyrazole [1,5a] pyrimid-2-yl] thionophosphate Ethyl 2-[(diethoxyphosphorothioyl)oxy]-5-methylpyrazolo[1,5-a]pyrimidine-6-carboxylate O,O-Diethyl-O-(5-methyl-6-ethoxy-carbonyl-pyrazolo(1.5-a)pyrimid-2-yl)-thionophosphate O，O-diethyl-O-(6-ethoxyearbonyl-5-methylpyrazolo[1,5α] pyrimidin-2-yl) thionophosphate O,O-DIETHYL-O-6-ETHOXYCARBONYL-5-METHYL-PYRAZOLO [1,5-A]PYRIMIDIN-2-YL-PHOSPHOROTHIONATE 0,0-Diethyl ester-0-6-ethoxycarbonyl-5-methyl)-pirazol-(1,5-pyrilidin-2-ol)-thiophosphoric acid pyrazolo[1,5-a]pyrimidine-6-carboxylicacid,2-[(diethoxyphosphinothioyl)oxy]-5-methyl-,ethylester Pyrazolo[1,5-a]pyrimidine-6-carboxylic acid, 2-[(diethoxyphosphinothioyl)oxy]-5-methyl-, ethyl ester phosphorothioicacid,o,o-diethylester,o-esterwith(6-ethoxycarbonyl-5-methyl)pyrazolo(1,5-a)pyrimidin-2-ol pyrazophos (ISO) O,O-diethyl O-(6-ethoxycarbonyl-5-methylpyrazolo[2,3-a]pyrimidin-2-yl) phosphorothioate Ethyl 2-hydroxy-5-methylpyrazolo(1,5-a)pyrimidine-6-carboxylate O-ester of O,O-diethylphosphorothioic acid Phosphorothioic acid, O,O-diethyl ester O-ester with (6-ethoxycarbonyl-5-methyl)pyrazolo(1,5-pyrimidin-2-ol) phosphorothioicacid,o,o-diethylester,esterwithethyl-2-hydroxy-5-methylpyrazolo[1,5-a]pyrimidine-6-carboxylate Phosphorothioic acid, O,O-diethyl ester, O-ester with (6-ethoxycarbonyl-5-methyl)pyrazolo(1,5-a)pyrimidin-2-ol Pyrazolo[1,5-a]pyrimidine-6-carboxylic acid, 2-hydroxy-5-methyl-, ethyl ester, O-ester with O,O-diethyl phosphorothioate

Chemical Properties

Melting point	51℃
density	1.38±0.1 g/cm3(Predicted)
vapor pressure	2.2 x 10^-4 Pa (50 °C)
storage temp.	APPROX 4°C
form	neat
pka	-1.37±0.40(Predicted)
Water Solubility	4.2 mg l^-1 (25 °C)
Merck	13,8052
BRN	577209
Major Application	agriculture environmental
InChI	1S/C14H20N3O5PS/c1-5-19-14(18)11-9-17-12(15-10(11)4)8-13(16-17)22-23(24,20-6-2)21-7-3/h8-9H,5-7H2,1-4H3
InChIKey	JOOMJVFZQRQWKR-UHFFFAOYSA-N
SMILES	CCOC(=O)c1cn2nc(OP(=S)(OCC)OCC)cc2nc1C
EPA Substance Registry System	Pyrazophos (13457-18-6)

Safety Data

Hazard Codes	Xn,N
Risk Statements	20/22-50/53 less more
Safety Statements	36/37-46-60-61 less more
RIDADR	2783
WGK Germany	3
RTECS	TF2035000
HazardClass	6.1(b)
PackingGroup	III
Storage Class	6.1C - Combustible, acute toxic Cat.3 toxic compounds or compounds which causing chronic effects
Hazard Classifications	Acute Tox. 3 Oral Acute Tox. 4 Inhalation Aquatic Acute 1 Aquatic Chronic 1
Toxicity	LD50 in rats, marmots, rabbits (mg/kg): 140, 184, 435 orally (Smit) less more

Hazard Information

Chemical Properties

The pure product is colorless crystals. MPa is 51-53°C, relative density is 1.348 (25°C), vapor pressure is >0.133×10-3 Pa (20°C), 0.221×10-3 Pa (50°C). Solubility at 20°C: acetone 121.2%, toluene >98%, ethyl acetate 89.8%, ethanol 9.5%, n-hexane 1.1%, water 0.42% (0.03%). It is also soluble in organic solvents such as benzene, xylene, carbon tetrachloride, and trichloroethylene. It readily decomposes under acidic and alkaline conditions, but will not decompose significantly when stored in dry conditions for two years.

Uses

Fungicide.

Uses

Pyrazophos 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.

Definition

ChEBI: 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.

Metabolic pathway

Limited information is available to describe the degradation and metabolic fate of pyrazophos. Hydrolytic cleavage of the P-O-pyrazolopyrimidine linkage is the primary metabolic pathway. Oxidative desulfuration of pyrazophos to pyrazophos-oxon is only a minor pathway, observed in the plant metabolism study (Scheme 1).

Metabolism

Its mode of action is believed to be the inhibition of melanin biosynthesis and the development of appressoria by fungal conidia. Formulation is available as emulsifiable concentrate (EC: 30%). Application rates on Oidium spp. are in the range of 15–30 g a.i./hl.

Degradation

Pyrazophos (1) is hydrolysed in acidic or alkaline solution (PM).

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