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Isoprothiolane

HCID 39681
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Basic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
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Basic information

CAS
50512-35-1
Standard SMILES
CC(C)OC(=O)C(C(=O)OC(C)C)=C1SCCS1
InChIKey
UFHLMYOGRXOCSL-UHFFFAOYSA-N
Molecular formula
C12H18O4S2
Average molar mass
290.4 g/mol
Monoisotopic mass
290.0646514

Overview

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 an isopropyl ester, a malonate ester and a member of dithiolanes. It is functionally related to a malonic acid. It derives from a hydride of a 1,3-dithiolane.

Names & identifiers

Preferred name
Isoprothiolane
IUPAC
dipropan-2-yl 2-(1,3-dithiolan-2-ylidene)propanedioate
English name
Isoprothiolane
Molecular formula
C12H18O4S2
Molecular weight
290.4

Names & synonyms

ISOPROTHIOLANE50512-35-1Fuji-oneNKK 100bis(1-methylethyl) 1,3-dithiolan-2-ylidenepropanedioateDi-isopropyl 1,3-dithiolane-2-ylidenemalonatediisopropyl 1,3-dithiolan-2-ylidenemalonatePropanedioic acid, 1,3-dithiolan-2-ylidene-, bis(1-methylethyl) esterDTXSID8058110NNF 10988HCS898G6di(propan-2-yl) 1,3-dithiolan-2-ylidenemalonate
Show more names
IPTPropanedioicacid,1,3-dithiolan-2-ylidene-,bis(1-methylethyl)esterfuji1nkk100Fuji 1ISORANVIFUSINNF-109
CHEBI:60471,3-Dithiolan-2-ylidenepropanedioic acid, bis(1-methylethyl) ester1,3-bis(propan-2-yl) 2-(1,3-dithiolan-2-ylidene)propanedioateRefChem:792266DTXCID7031878FudiolanDiisopropyl 2-(1,3-dithiolan-2-ylidene)malonateFujione

Database identifiers

CAS

Properties

Computed structural properties

XLogP
3.3
Topological polar surface area
103 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
6
Rotatable bonds
6
Heavy atoms
18
Formal charge
0
Complexity
329

Experimental & physicochemical properties

Pesticides · 3 items

Fungicides

Active substance -> EU Pesticides database: Not approved

Pesticide (Isoprothiolane) -> USDA PDB

LogP · 2 items

2.88

3.3

Solubility0.054 mg/mL at 25 °C
Endocrine DisruptorsPotential endocrine disrupting compound
Melting Point50 - 54.5 °C
Physical DescriptionSolid

Physicochemical properties

Melting point
54 °C · 54°C
Boiling point
402.48 °C · 402.48°C (rough estimate)
Density
1.3402 · 1.3402 (rough estimate)
vapor pressure
1.9 Pa · 1.9 Pa (25 °C)
refractive index
1.495 · 1.4950 (estimate)

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 · 6 items

Warning

H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]

P264, P270, P273, P301+P317, P330, P391, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 83 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

H401: Toxic to aquatic life [Hazardous to the aquatic environment, acute hazard]

P273, P391, and P501 (click each P-code to see the statement)

Hazard information

Regulatory Information2002/2076
Hazard Classes and Categories · 3 items

Acute Tox. 4 (100%)

Acute toxicity (Oral) - Category 4

Hazardous to the aquatic environment (Acute) - Category 2

Safety data

wgk
3
ridadr
UN 3077 9 / PGIII
hs_code
29341000
Toxicity
LD50 oral in rabbit: 2320mg/kg
risk_code
22-51/53
Signal word
Warning
Symbol(GHS)
GHS07
hazard_code
Xn,N
safety_code
61
Storage Class
11 - Combustible Solids
Hazard statements
H302
Hazard Classifications

Chemistry & industry

Pharmacology

Cellular LocationsMembrane

Applications

UsesIsoprothiolane is a dithiolane pesticide. Isoprothiolane is commonly used in agriculture as a fungicide to control planthoppers and blast disease in rice plants.

UsesIsoprothiolane 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.

Upstream & downstream products

Upstream raw materials

Diisopropyl malonateIsopropylmalonic acidHexaneCarbon disulfideSodium cyanideBenzeneMalonic acid disodium saltIsopropyl alcoholDichloroethaneSulfuric acidSodium chloroacetate3,6,7,10-Tetrathiadodeca-1,11-diene-1,1,12,12-tetracarboxylic acid, 2,11-dimethoxy-, tetrakis(1-methylethyl) ester, 6-oxide (9CI)

Related reactions

4 records
New reaction record
HRID 252887 reaction equation
HRID 252887As reactantuspto-grants-2011_01
HRID 1029792 reaction equation
HRID 1029792As reactantuspto-grants-1992_04
HRID 2054730 reaction equation
HRID 2054730As reactantuspto-grants-2008_02
HRID 2140507 reaction equation
HRID 2140507As reactantTraining data from https://doi.org/10.1039/C8SC04228D (4/10)

Compound notes

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On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
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50512-35-1
PubChem CID
39681
DTXSID
DTXSID8058110
ChEMBL
CHEMBL35280
ChEBI
CHEBI:6047
UNII
88HCS898G6
EC Number
610-537-8
Nikkaji
J3.513K
storage temp.
2 · Keep in dark place,Sealed in dry,2-8°C
solubility
Chloroform (Slightly), Ethyl Acetate (Slightly)
form
Solid
Water Solubility
54 mg · 54 mg l-1 (25 °C)
color
Light yellow to yellow
BRN
2128528 · 2128528
Henry's Law Constant
9.8 · 9.8×10-2 mol/(m3Pa) at 25℃, Duchowicz et al. (2020)
Major Application
agricultureenvironmental
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 · 50512-35-1(CAS DataBase Reference)
EWG's Food Scores
1 · 1
FDA UNII
88 HCS898G6 · 88HCS898G6
NIST Chemistry Reference
1 · Propanedioic acid, 1,3-dithiolan-2-ylidene-, bis(1-methylethyl) ester(50512-35-1)
EPA Substance Registry System
1 · Propanedioic acid, 1,3-dithiolan-2-ylidene-, bis(1-methylethyl) ester (50512-35-1)
UNSPSC Code
41116107 · 41116107
NACRES
24 · NA.24
Symbol(GHS)
7 · GHS07
Signal word
Warning
Hazard statements
302 · H302
Precautionary statements
264 · P264-P270-P301+P312-P330-P501
Hazard Codes
Xn,N
Risk Statements
22 · 22-51/53
Safety Statements
61 · 61
RIDADR
3077 · UN 3077 9 / PGIII
WGK Germany
3 · 3
HS Code
29341000 · 29341000
Storage Class
11 · 11 - Combustible Solids
Hazard Classifications
4 Oral · Acute Tox. 4 Oral
Toxicity
50 oral · LD50 oral in rabbit: 2320mg/kg
Acute Tox. 4 Oral
Precautionary statements
P264-P270-P301+P312-P330-P501
L-Cysteine methyl ester hydrochloride
Additional notes · 1 item

DefinitionChEBI: 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.