26087-47-8 Usage
Description
Iprobenfos, an organic thiophosphate, is the S-benzyl O,O-diisopropyl ester of phosphorothioic acid. It is a systemic fungicide known for its effectiveness in controlling various fungal diseases in rice.
Used in Agriculture:
Iprobenfos is used as a rice fungicide for the effective protective and curative control of leaf and ear blast (Pyricularia oryzae), stem rot (Helminthosporium spp.), and sheath blight (Rhizoctonia solani). Its systemic nature allows it to be absorbed by the plant and distributed throughout, providing comprehensive protection against these fungal infections.
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).
Check Digit Verification of cas no
The CAS Registry Mumber 26087-47-8 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 2,6,0,8 and 7 respectively; the second part has 2 digits, 4 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 26087-47:
(7*2)+(6*6)+(5*0)+(4*8)+(3*7)+(2*4)+(1*7)=118
118 % 10 = 8
So 26087-47-8 is a valid CAS Registry Number.
InChI:InChI=1/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
26087-47-8Relevant articles and documents
Sulfonyl-Promoted Michaelis-Arbuzov-Type Reaction: An Approach to S/Se-P Bonds
Rather, Suhail A.,Bhat, Mohammad Yaqoob,Hussain, Feroze,Ahmed, Qazi Naveed
, p. 13644 - 13663 (2021/10/01)
By facilitating the chemical conversion of thiols to thiosulfonates, phosphoramidite/phosphite bearing sp3-hybridized carbon serves as an ideal coupling material to forge new connections at room temperature. In this work, a functional group-induced, additive-free, novel, S-P bond-forming approach is presented. This protocol exhibits good functional group tolerance with wide applications that include phosphorylation of cysteine derivatives, development of a one-pot approach to mixed unsymmetrical thiophosphonates, and extension of the concept to different Se-P bonds. Meticulously, our reaction also generated a S-P bond against cyclic 1,2-dithiane-1-dioxide in a byproduct-free manner. These Michaelis-Arbuzov-type reactions are easy to conduct, work efficiently in a reduced reaction time, and are applicable to gram-scale preparation as well.
Benign synthesis of thiophosphates, thiophosphinates and selenophosphates in neat condition using N-chalcogenoimides as the source of electrophilic sulfur/selenium
Mondal,Saha, Amit
supporting information, (2019/08/08)
A neat reaction protocol has been developed for synthesis of thiophosphate, thiophosphinate and selenophosphate compounds. N-chalcogenoimides have been used for chalcogenylation of P(O)H moieties of various H-phosphonates under solvent, catalyst and base free condition at room temperature in aerial atmosphere. Both S-aryl and S-alkyl phosphorothioate compounds were prepared by this method in good yields. Selenophosphates were also synthesized using N-(phenylseleno)phthalimide under solvent free condition.
Synthetic method for benzyl thiophosphate
-
Paragraph 0024-0028, (2019/02/06)
The invention provides a synthetic method for benzyl thiophosphate. The method comprises the step of carrying out a stirring reaction for 6-24 hours on benzyl alcohol which is cheap and easily available, wide in source and stable and low in toxicity as an alkylation reagent and sulfur powder and phosphite ester to prepare a benzyl thiophosphate compound in one step at 70-100 DEG C without a catalyst. The method is simple in reaction condition, the raw materials are easily available, excessive alkali is not used, a solvent is not needed, and the method is easy to operate with only one reaction.The method can be also used for amplifying and gram-grade preparation of products conveniently, and has certain research and industrial application prospects.
