| Identification | More | [Name]
Iprobenfos | [CAS]
26087-47-8 | [Synonyms]
BLATAF(R)
IBP
IPROBENFOS
IPROBENPHOS
KITAZIN
KITAZINE
KITAZIN P
KITAZIN(R)
o，o-Diethyl-s-benzylthiophosphate
S-BENZYL O,O-DI-ISOPROPYL-PHOSPHOROTHIOATE
iprofenfos
Kitazin L
kitazinl
O,O-bis(1-Methylethyl)-S-(phenylmethyl)phosphorothiolate
O,O-Diisopropyl S-Benzyl phosphorothioate
O,O-Diisopropyl S-benzyl thiophosphate
o,o-diisopropyl-s-benzylesterkyselinythiofosforecne
o,o-diisopropyls-benzylphosphorothiolate
o,o-diisopropyls-benzylthiophosphate
Phosphorothioic acid, O,O-bis(1-methylethyl) S-(phenylmethyl) ester | [EINECS(EC#)]
247-449-0 | [Molecular Formula]
C13H21O3PS | [MDL Number]
MFCD00191226 | [Molecular Weight]
288.34 | [MOL File]
26087-47-8.mol |
| Chemical Properties | Back Directory | [Melting point ]
25°C | [Boiling point ]
126°C | [density ]
1.1001 g/cm3 | [vapor pressure ]
2.5 x 10-4 Pa (20 °C) | [refractive index ]
approximate 1.51 | [Fp ]
11 °C | [storage temp. ]
APPROX 4°C
| [form ]
liquid | [Water Solubility ]
430 mg l-1(20 °C) | [color ]
Colorless to light yellow | [biological source]
rabbit | [BRN ]
1974687 | [Henry's Law Constant]
2.6×102 mol/(m3Pa) at 25℃, Watanabe (1993) | [Exposure limits]
PC-TWA: 2 mg/m3; PC-STEL: 5 mg/m3 | [Major Application]
agriculture
environmental | [InChI]
1S/C13H21O3PS/c1-11(2)15-17(14,16-12(3)4)18-10-13-8-6-5-7-9-13/h5-9,11-12H,10H2,1-4H3 | [InChIKey]
FCOAHACKGGIURQ-UHFFFAOYSA-N | [SMILES]
CC(C)OP(=O)(OC(C)C)SCc1ccccc1 | [CAS DataBase Reference]
26087-47-8(CAS DataBase Reference) | [NIST Chemistry Reference]
Kitazin p(26087-47-8) | [EPA Substance Registry System]
Phosphorothioic acid, O,O-bis(1-methylethyl) S-(phenylmethyl) ester (26087-47-8) |
| Safety Data | Back Directory | [Hazard Codes ]
Xn;N,N,Xn,T,F | [Risk Statements ]
R22:Harmful if swallowed.
R51/53:Toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment .
R39/23/24/25:Toxic: danger of very serious irreversible effects through inhalation, in contact with skin and if swallowed .
R23/24/25:Toxic by inhalation, in contact with skin and if swallowed .
R11:Highly Flammable. | [Safety Statements ]
S61:Avoid release to the environment. Refer to special instructions safety data sheet .
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) .
S36/37:Wear suitable protective clothing and gloves . | [RIDADR ]
UN 3082 | [WGK Germany ]
2 | [RTECS ]
TE6550000 | [HazardClass ]
6.1(a) | [PackingGroup ]
II | [HS Code ]
29309090 | [Storage Class]
10 - Combustible liquids | [Hazard Classifications]
Acute Tox. 4 Oral
Aquatic Chronic 2 |
| Hazard Information | Back Directory | [Chemical Properties]
The pure product is a colorless, transparent liquid with a bp of 126°C/5.332 Pa, a relative density of 1.107, an mp of 22.5-23.8°C, and a refractive index n20D of 1.5106. It is readily soluble in various organic solvents but insoluble in water. It is relatively stable to light and acid but readily decomposes in the presence of alkaline substances. The industrial product is a pale yellow, oily liquid. | [Uses]
Iprobenfos is a systemic fungicide which provides effective
protective and curative control of leaf and ear blast (Pyricularia oryzae),
stem rot (Helminthosporium spp.) and sheath blight (Rhizoctonia solani) in
rice. | [Definition]
ChEBI: An organic thiophosphate that is the S-benzyl O,O-diisopropyl ester of phosphorothioic acid. Used as a rice fungicide to control leaf and ear blast, stem rot and sheath blight. | [Production Methods]
The industrial production of iprobenfos involves the reaction of phosphorothioic acid with benzyl alcohol and isopropanol to form S-benzyl-O,O-diisopropyl phosphorothioate. This process typically includes controlled esterification under anhydrous conditions, followed by purification steps such as distillation or crystallisation to achieve high purity. | [Mechanism of action]
Systemic, with both curative and protective properties. Absorbed through roots and translocated. Phospholipid biosynthesis inhibitor | [Metabolic pathway]
Iprobenfos undergoes extensive degradation and metabolism. Primary
metabolic pathways include isomerisation to the thionate (P=S) ester,
cleavage of the P-S-benzyl and P-O-isopropyl moieties, and transesterification.
Benzyl mercaptan, upon cleavage, undergoes additional
oxidation reactions to yield the alcohol, carboxylic acid, disulfide and
sulfonic acid. The formation of the oxon from the isomerisation product
(P=S ester) was minor and was observed only under UV light irradiation.
The primary metabolic pathways of iprobenfos are presented in
Scheme 1. | [Degradation]
Iprobenfos (1) is stable to hydrolytic degradation (<50 °C). The DTN
value of iprobenfos in aqueous solution was approximately 301-324 days(PM).
Iprobenfos degraded rapidly when deposited as a thin film and
exposed to UV light (DT50 ca. 10 min). Two major degradation reactions
were observed during the initial phase of the irradiation. The first reaction
involved the isomerisation of iprobenfos to O,O-diisopropyl O-
benzyl phosphorothioate (2) followed by the oxidative desulfuration
of compound 2 to yield the corresponding oxon analogue 3 (O,O-diisopropyl
O-benzyl phosphate). The second reaction involved the
hydrolytic cleavage of the S-C linkage of iprobenfos to yield O,O-diisopropyl
hydrogen phosphorothioate (4) and the cleavage of the
P-O-benzyl linkage of compound 3 to yield O,O-diisopropyl hydrogen
phosphate (5). Other major photolytic degradation reactions include the
cleavage of the parent P-S linkage to O,O-diisopropyl phosphonate (6).
Benzyl alcohol (7) and benzyl mercaptan (8) were also detected. Further
oxidation of compound 7 yielded benzoic acid (9) and the oxidation
of compound 8 yielded benzylsulfonic acid (10), dibenzyl disulfide (11)
and sulfuric acid as terminal products. Other minor products detected
included transesterification products [O,O,S-triisopropyl phosphorothioate
(12), O,O,O-triisopropyl phosphate (13)] and benzyl isopropyl
sulfide (14). | [Pesticide Type]
Fungicide |
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