| Identification | More | [Name]
Isoprothiolane | [CAS]
50512-35-1 | [Synonyms]
Bis(1-methylethyl) 1,3-dithiolan-2-ylidenepropanedioate
DI-ISOPROPYL 1,3-DITHIOLAN-2-YLINDENE MALONATE
FUJI-ONE
FUJI-ONE(R)
IPT
ISOPROTHIOLANE
ISORAN
VIFUSI
1,3-dithiolan-2-ylidene-propanedioicacibis(1-methylethyl)ester
Di-isopropyl 1,3-dithiolane-2-ylidenemalonate
Diisopropyl 2-(1,3-dithiolan-2-ylidene)malonate
di-Isopropyl1,3-dithiolan-2-ylidenemalonate
Diisopropyl1,3-dithiolan-2-ylidenemalonate
di-isopropyl1,3-dithiolane-2-ylidenemalonate
diisopropyl-2(1,3-dithiolan-2-ylidene)malonate
Fudiolan
Fuji 1
fuji1
NKK 100
nkk100 | [Molecular Formula]
C12H18O4S2 | [MDL Number]
MFCD00210314 | [Molecular Weight]
290.4 | [MOL File]
50512-35-1.mol |
| Chemical Properties | Back Directory | [Melting point ]
54°C | [Boiling point ]
402.48°C (rough estimate) | [density ]
1.3402 (rough estimate) | [vapor pressure ]
1.9 Pa (25 °C) | [refractive index ]
1.4950 (estimate) | [storage temp. ]
0-6°C | [solubility ]
Chloroform (Slightly), Ethyl Acetate (Slightly) | [form ]
neat | [Water Solubility ]
54 mg l-1 (25 °C) | [color ]
Light yellow to yellow | [BRN ]
2128528 | [Henry's Law Constant]
9.8×10-2 mol/(m3Pa) at 25℃, Duchowicz et al. (2020) | [Major Application]
agriculture
environmental | [InChI]
1S/C12H18O4S2/c1-7(2)15-10(13)9(11(14)16-8(3)4)12-17-5-6-18-12/h7-8H,5-6H2,1-4H3 | [InChIKey]
UFHLMYOGRXOCSL-UHFFFAOYSA-N | [SMILES]
CC(C)OC(=O)\C(C(=O)OC(C)C)=C1/SCCS1 | [CAS DataBase Reference]
50512-35-1(CAS DataBase Reference) | [NIST Chemistry Reference]
Propanedioic acid, 1,3-dithiolan-2-ylidene-, bis(1-methylethyl) ester(50512-35-1) | [EPA Substance Registry System]
50512-35-1(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
Xn,N | [Risk Statements ]
22-51/53 | [Safety Statements ]
61 | [RIDADR ]
UN 3077 9 / PGIII | [WGK Germany ]
3 | [HS Code ]
29341000 | [Storage Class]
11 - Combustible Solids | [Hazard Classifications]
Acute Tox. 4 Oral | [Toxicity]
LD50 oral in rabbit: 2320mg/kg |
| Raw materials And Preparation Products | Back Directory | [Raw materials]
Sulfuric acid-->Benzene-->Hexane-->Isopropyl alcohol-->Sodium cyanide-->Carbon disulfide-->Dichloroethane-->Sodium chloroacetate-->MALONIC ACID DISODIUM SALT-->Diisopropyl malonate-->Isopropylmalonic acid-->3,6,7,10-Tetrathiadodeca-1,11-diene-1,1,12,12-tetracarboxylic acid, 2,11-dimethoxy-, tetrakis(1-methylethyl) ester, 6-oxide (9CI)-->L-Cysteine methyl ester hydrochloride |
| Hazard Information | Back Directory | [Hazard]
Moderately toxic by ingestion. | [Uses]
Isoprothiolane is a dithiolane pesticide. Isoprothiolane is commonly used in agriculture as a fungicide to control planthoppers and blast disease in rice plants. | [Uses]
Isoprothiolane is a fungicide that is used to control rice blast
(Pyriculuriu aryzae), rice stem rot and Fusarium leaf spot on rice. It also
reduces the plant-hopper population on rice. | [Definition]
ChEBI: Isoprothiolane is a malonate ester that is diisopropyl malonate in which the two methylene hydrogens at position 2 are replaced by a 1,3-dithiolan-2-ylidene group. An insecticide and fungicide used to control a range of diseases including Pyricularia oryzae, Helminthosporium sigmoideum and Fusarium nivale. It has a role as an insecticide, an environmental contaminant, a phospholipid biosynthesis inhibitor and an antifungal agrochemical. It is a malonate ester, a member of dithiolanes and an isopropyl ester. It is functionally related to a malonic acid. It derives from a hydride of a 1,3-dithiolane. | [Production Methods]
The industrial synthesis of isoprothiolane begins with the key intermediate diisopropyl malonate, which undergoes alkylation and cyclisation reactions to form a 1,3-dithiolane ring, a five-membered heterocycle containing two sulphur atoms. This ring structure is essential for the fungicide’s biological activity. The process involves reacting diisopropyl malonate with chlorinated acetals or aldehydes under acidic conditions to facilitate ring closure. Subsequent steps include esterification and purification through solvent extraction or distillation to yield the active compound. | [Mechanism of action]
Systemic with protective and curative action. Phospholipid biosynthesis inhibitor (methyltransferase/group 2) | [Metabolic pathway]
Isoprothiolane is easily oxidized by rat liver 9000 g
supernatant to produce its racemic sulfoxide in this
process, NADPH is an effective cofactor but NADH is
not. The liver microsomes, however, preferentially
form its (?+)-isomer in an enantiomeric excess of
38-43%. The sulfoxidation of isoprothiolane by rice
plants proceeds too slowly to determine the
metabolites. Both isoprothiolane (+?)- and (-)-
sulfoxides undergo rapid racemization by rat cytosol
(105 000 g supernatant) or rice plants, accompanied
with reduction to isoprothiolane. | [Degradation]
Half-lives of isoprothiolane in river water were greater than 50 days
(Hayakawa et. al., 1992). The compound is decomposed slowly in deionised
water under UV light or sunlight. In rice paddy water, photodegradation
was greatly accelerated by the presence of natural organic
constituents (Chou and Eto, 1980; Eto et al., 1979). Isoprothiolane was
placed on a silica gel TLC plate and irradiated at 10 cm distance with a
10 W lamp emitting mainly at 254 nm. Isoprothiolane photodegraded
rapidly (half-life about 3 hours). Five products were detected. Proposed
pathways of photodegradation are shown in Scheme 1 and involved
cleavage of the dithiolane ring, ester hydrolysis, decarboxylation and the
formation of dimeric heterocyclic compounds. The identities of oxalic acid
(2), dithiolanylidenemalonic acid (3), dithiolanylideneacetic acid (4), 2,4-
bis[bis(isopropoxycarbonyl)methylene]-1,3-dithietane (5), 3,5-bis[bis(isopropoxycarbonyl)
methylene]-1,2,4-trithiolane (6) and elemental sulfur
were confirmed. Isoprothiolane degraded more rapidly on sand than on
a glass plate (Chou and Eto, 1980). | [Pesticide Type]
Fungicide; Insecticide |
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