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Thioquinox

HCID 7159
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Basic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
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Basic information

CAS
93-75-4
Standard SMILES
S=c1sc2nc3ccccc3nc2s1
InChIKey
ILERPRJWJPJZDN-UHFFFAOYSA-N
Molecular formula
C9H4N2S3
Average molar mass
236.3 g/mol
Monoisotopic mass
235.95366166

Overview

Thioquinox is a quinoxaline antifungal agent, a quinoxaline acaricide and a dithioloquinoxaline.

Names & identifiers

Preferred name
Thioquinox
IUPAC
[1,3]dithiolo[4,5-b]quinoxaline-2-thione
English name
Thioquinox
Molecular formula
C9H4N2S3
Molecular weight
236.34

Names & synonyms

THIOQUINOXQuinothionate93-75-4ChinothionatThiaquinoxReadex[1,3]dithiolo[4,5-b]quinoxaline-2-thioneThioquinox [ISO]Bayer 30686Caswell No. 720Quinoxaline-2,3-diyl trithiocarbonate1,3-Dithiolo[4,5-b]quinoxaline-2-thione
Show more names
ss1451B-31686bay30686ent25,579Ai3-25579bayer30686ss1451[qr]
2-Thioxo-1,3-dithiolo(4,5-b)quinoxalineBAY 30686Eraditon2,3-Quinoxalinedithiol cyclic-trithiocarbonateENT 25,5792,3-Quinoxalinedithiol, cyclic trithiocarbonateSS 14512-Thio-1,3-dithio(4,5-b)quinoxaline

Database identifiers

CAS
93-75-4
PubChem CID
7159
DTXSID
DTXSID3042471
ChEBI
CHEBI:38822
UNII
0DRA4L621C
EC Number
202-272-8
Nikkaji
J4.684A

Properties

Computed structural properties

XLogP
3.3
Topological polar surface area
108 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
5
Rotatable bonds
0
Heavy atoms
14
Formal charge
0
Complexity
234

Experimental & physicochemical properties

PesticidesPesticides -> Other Insecticides
LogPlog Kow = 1.3 /Estimated/
OdorOdorless
Color/FormBrownish yellow solid
Solubility · 3 items

Slightly soluble in acetone, methanol. Anhydrous ethanol, -petroleum ether and kerosene

Insoluble in water

PRACTICALLY INSOL IN MOST ORG SOLVENTS

Melting Point180 °C
Vapor Pressure · 2 items

0.00000006 [mmHg]

1X10-7 mm Hg at 20 °C

Physical DescriptionBrownish-yellow odorless solid; [HSDB]
Stability/Shelf Life · 2 items

Stable to 200 °C and to light. Susceptible to oxidation to s-oxides without reduction of biological activity

At room temperature, extremely stable against hydrolytic effects ...

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: Harmful if swallowed [Warning Acute toxicity, oral]

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

Warning

H302: Harmful if swallowed [Warning Acute toxicity, oral]

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

Hazard information

Hazards Summary · 1 item

Technical product caused skin irritation in 2 of 8 people tested; No adverse effects in rats after skin applications of 3000 mg/kg; Rats fed 100 mg/kg/day for 2 weeks had weakness, weight loss, and one death; Lethal human dose is probably 1 ounce to 1 pint; [HSDB]

Hazard Classes and Categories · 2 items

Acute toxicity - category 4

Acute Tox. 4 *

Skin, Eye, and Respiratory Irritations... Technical product caused irritation to forearms of 2 of 8 people tested.

Safety & protection

Preventive Measures · 4 items

SRP: Local exhaust ventilation should be applied wherever there is an incidence of point source emissions or dispersion of regulated contaminants in the work area. Ventilation control of the contaminant as close to its point of generation is both the most economical and safest method to minimize personnel exposure to airborne contaminants.

SRP: Contaminated protective clothing should be segregated in such a manner so that there is no direct personal contact by personnel who handle, dispose, or clean the clothing. Quality assurance to ascertain the completeness of the cleaning procedures should be implemented before the decontaminated protective clothing is returned for reuse by the workers. Contaminated clothing should not be taken home at end of shift, but should remain at employee's place of work for cleaning.

Chemistry & industry

Uses & manufacturing

Uses · 6 items

Used as a non-systemic acaricide (effective against eggs) and fungicide (specific against powdery mildews); Not currently registered with the EPA for use in the US; [HSDB]

Farming (Pesticides) [Category: Industry]

For thioquinox (USEPA/OPP Pesticide Code: 084401) there are 0 labels match. /SRP: Not registered for current use in the U.S., but approved pesticide uses may change periodically and so federal, state and local authorities must be consulted for currently approved uses./

Good ovicide for control of spiders on ornamentals

Thioquinox is a non-systemic acaricide effective against eggs; a fungicide specific against powdery mildews

Fungicide, acaricide.

Methods of Manufacturing · 3 items

Made by reaction of thiophosgene and quinoxaline-2,3-dithiol...

/It is manufactured/ by reaction of phosgene and 2,3-dimercapto-quinoxaline.

Preparation: Sasse et al, US 3141886 (1964 to Bayer); DE 1088965 (1960); BE 580478 (1958).

Formulations/Preparations · 3 items

/It is/ formulated as: 'eradex', 25% and 50% wettable powders.

Eradex

Erazidon

General Manufacturing Information · 4 items

It was introduced, in 1957, by Bayer Leverkusen under code numbers 'Bayer 30686' & 'SS1451', Trademark 'eradex' & protection of Belgian Patent 580,478.

Product discontinued by Bayer AG, Federal Republic of Germany.

Withdrawn for registration in North America because of skin sensitizing effect.

Not recommended /to mix with/ Morestan

Applications

UsesThioquinox is a fungicide/insecticide used in pesticide formulations. Toxic to various species of mites. A member of the quinoxoline class of pesticides.

UsesAcaricide, fungicide.

Suppliers6 total

Related reactions

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Compound notes

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On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
Other Experimental Properties
Begins to melt at 165 °C but does not decompose until temp exceeds 200 °C /Technical/

Physicochemical properties

Melting point
180 ° · 180°
Henry's Law Constant
1.3 · 1.3×102 mol/(m3Pa) at 25℃, HSDB (2015)
EWG's Food Scores
1 · 1
FDA UNII
0 DRA4L621C · 0DRA4L621C
EPA Substance Registry System
Thioquinox (93-75-4)
Symbol(GHS)
7 · GHS07
Signal word
Warning
Hazard statements
302 · H302
Precautionary statements
264 · P264-P270-P301+P312-P330-P501
Hazard Codes
Xn
Risk Statements
22 · 22
Safety Statements
24 · 24
HS Code
29349990 · 29349990
Hazardous Substances Data
93 · 93-75-4(Hazardous Substances Data)
Toxicity
50 orally · LD50 orally in rats: 3.4 g/kg (Sasse)

Avoid skin contact and inhalation of the dust.

Apparently has low inhalation hazard.

Toxicology

Environmental Fate · 3 items

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 150(SRC), determined from a structure estimation method(2), indicates that thioquinox is expected to have moderate mobility in soil(SRC). Volatilization of thioquinox from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 7.8X10-8 atm-cu m/mole(SRC), using a fragment constant estimation method(3). Thioquinox is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 1X10-7 mm Hg(4). Biodegradation data were not available(SRC, 2005).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 150(SRC), determined from a structure estimation method(2), indicates that thioquinox is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 7.8X10-8 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). According to a classification scheme(5), an estimated BCF of 2(SRC), from an estimated log Kow of 1.3(6) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Biodegradation data were not available(SRC, 2005).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), thioquinox, which has a vapor pressure of 1X10-7 mm Hg at 25 °C(2), is expected to exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase thioquinox is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 2 days(SRC), calculated from its rate constant of 7.9X10-12 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Particulate-phase thioquinox may be removed from the air by wet and dry deposition(SRC). Thioquinox has been reported to be stable to light(4).

Soil Adsorption/Mobility · 1 item

Using a structure estimation method based on molecular connectivity indices(1), the Koc for thioquinox can be estimated to be 150(SRC). According to a classification scheme(2), this estimated Koc value suggests that thioquinox is expected to have moderate mobility in soil.

Human Toxicity Excerpts/OTHER TOXICITY INFORMATION/ ... Technical product caused irritation to forearms of 2 of 8 people tested.
Artificial Pollution SourcesThioquinox's former production and use as an acaricide and fungicide(1) resulted in its direct release to the environment(SRC).
Environmental Bioconcentration · 1 item

An estimated BCF of 2 was calculated for thioquinox(SRC), using an estimated log Kow of 1.3(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is low(SRC).

Volatilization from Water/Soil · 1 item

The Henry's Law constant for thioquinox is estimated as 7.8X10-8 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that thioquinox is expected to be essentially nonvolatile from water surfaces(2). Thioquinox's Henry's Law constant indicates that volatilization from moist soil surfaces will not occur(SRC). Thioquinox is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 1X10-7 mm Hg(3).

Non-Human Toxicity Excerpts · 3 items

/LABORATORY ANIMALS: Acute Exposure/ ...Dermal applications of 3,000 mg/kg did not affect rats...

/LABORATORY ANIMALS: Subchronic or Prechronic Exposure/ In rats fed at levels of ...100 mg/kg/day it produced weakness, wt loss, and 1 death after 2 weeks.

/GENOTOXICITY/ Rec-assay procedure (H17 rec+ & M45 rec- Bacillus subtilis strains) and reversion assays on plates (auxotrophic strains of Escherichia coli (WP2) & Salmonella typhimurium (Ames series)) showed no evidence of thioquinox mutagenicity.

Environmental Abiotic Degradation · 1 item

The rate constant for the vapor-phase reaction of thioquinox with photochemically-produced hydroxyl radicals has been estimated as 7.9X10-12 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 2 days at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). Thioquinox has been shown to be resistant to hydrolysis(2). Thioquinox has been reported to be stable to light(2).

Probable Routes of Human Exposure · 1 item

Occupational exposure and general population exposure should be low or non-existent since thioquinox is no longer produced or used. In the past, thioquinox was applied directly to crops as an acaricide and fungicide and exposure to this compound was primarily by dermal contact and inhalation. (SRC)

Environmental Fate/Exposure Summary · 1 item

Thioquinox's former production and use as an acaricide and fungicde resulted in its direct release to the environment. If released to air, a vapor pressure of 1X10-7 mm Hg at 20 °C indicates thioquinox will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase thioquinox will be degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals; the half-life for this reaction in air is estimated to be 2 days. Particulate-phase thioquinox will be removed from the atmosphere by wet and dry deposition. Thioquinox has been shown to be stable to light. If released to soil, thioquinox is expected to have moderate mobility based upon an estimated Koc of 150. Volatilization from water and moist soil surfaces is not expected to be an important fate process based upon an estimated Henry's Law constant of 7.8X10-8 atm-cu m/mole. Thioquinox is not expected to volatilize from dry soil surfaces based upon its vapor pressure. If released into water, thioquinox is expected to adsorb to suspended solids and sediment based upon the estimated Koc. An estimated BCF of 2 suggests the potential for bioconcentration in aquatic organisms is low. Thioquinox has been reported to be resistant to hydrolysis because of the lack of hydrolyzable functional groups. Currently occupational exposure and general population exposure should be low or non-existent since thioquinox is no longer produced or used. In the past, thioquinox was applied directly to crops as an acaricide and fungicide and exposure to this compound was primarily by dermal contact and inhalation. (SRC)

Antidote and Emergency Treatment · 2 items

Basic treatment: Establish a patent airway. Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if needed. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with normal saline during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 ml/kg up to 200 ml of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool ... . Cover skin burns with dry sterile dressings after decontamination ... . /Poison A and B/

Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in respiratory arrest. Positive pressure ventilation techniques with a bag valve mask device may be beneficial. Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start an IV with D5W /SRP: "To keep open", minimal flow rate/. Use lactated Ringer's if signs of hypovolemia are present. Watch for signs of fluid overload. Consider drug therapy for pulmonary edema ... . For hypotension with signs of hypovolemia, administer fluid cautiously. Watch for signs of fluid overload ... . Treat seizures with diazepam (Valium) ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Poison A and B/

Non-Human Toxicity Values · 2 items

LD50 Rat oral 3.4 g/kg

LD50 guinea pigs oral 1.0 g/kg

Safety data

hs_code
29349990
Toxicity
LD50 orally in rats: 3.4 g/kg (Sasse)
risk_code
22
Signal word
Warning
Symbol(GHS)
GHS07
hazard_code
Xn
safety_code
24
Hazard statements
H302
Precautionary statements
P264-P270-P301+P312-P330-P501
Hazardous Substances Data
93-75-4(Hazardous Substances Data)
天津阿尔塔科技有限公司022-6537-8550 15522853686 · [email protected]
艾吉析科技(上海)有限公司17717235263 17717235263 · [email protected]
南通市苏北化工原料有限公司0513-85290972 18762756250 · [email protected]
SUZHOU SENFEIDA CHEMICAL CO.,LTD+86-0512-83500002 +86-15195660023 · [email protected]
上海杰股生物科技有限公司021-51698675 · [email protected]
南通众合化工新材料有限公司0513-85666561 15950816326 · [email protected]

Additional notes

DefinitionChEBI: Thioquinox is a quinoxaline acaricide, a quinoxaline antifungal agent and a dithioloquinoxaline.