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Difenzoquat metilsulfate

HCID 39424
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Basic information

CAS
43222-48-6
Standard SMILES
COS(=O)(=O)[O-].Cn1c(-c2ccccc2)cc(-c2ccccc2)[n+]1C
InChIKey
XQEMNBNCQVQXMO-UHFFFAOYSA-M
Molecular formula
C18H20N2O4S
Average molar mass
360.4 g/mol
Monoisotopic mass
360.1143783

Overview

Difenzoquat metilsulfate is a pyrazole herbicide. It is a derivative of difenzoquat. It is used as a postemergence herbicide to control wild oats in alfalfa, wheat and barley.

Names & identifiers

Preferred name
Difenzoquat metilsulfate
IUPAC
1,2-dimethyl-3,5-diphenylpyrazol-2-ium;methyl sulfate
English name
Difenzoquat methylsulfate
Molecular formula
C18H20N2O4S
Molecular weight
360.43

Names & synonyms

Difenzoquat methyl sulfateDifenzoquat metilsulfate43222-48-6Yeh-Yan-KuCaswell No. 363ADifenzoquat metilsulfate [ISO]DTXSID60240481,2-Dimethyl-3,5-diphenylpyrazolium methylsulphateEINECS 256-152-5UNII-6Y5I03RK7CEPA Pesticide Chemical Code 1064011,2-dimethyl-3,5-diphenyl-1H-pyrazol-2-ium methyl sulfate
Show more names
AVENGEac84777finavenYanmaikuAVENGE(R)Avenge SPAvenge 200Cifenzoquatmetilsulfatedifenzoquatmetilsulfate
6Y5I03RK7C1,2-Dimethyl-3,5-diphenyl-1H-pyrazolinium methyl sulfateDTXCID8040481H-Pyrazolium, 1,2-dimethyl-3,5-diphenyl-, methyl sulfateDIFENZOQUAT METHYL SULFATE [MI]AC-84777CL-847771H-PYRAZOLIUM, 1,2-DIMETHYL-3,5-DIPHENYL-, METHYL SULFATE (1:1)

Database identifiers

CAS
43222-48-6
PubChem CID

Properties

Computed structural properties

Topological polar surface area
83.6 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
4
Rotatable bonds
2
Heavy atoms
25
Formal charge
0
Complexity
342

Experimental & physicochemical properties

Pesticides · 2 items

Pesticide -> EPA IRIS

Pesticides -> Herbicides, Other

Physical DescriptionColorless to pale yellow odorless solid; [Reference #1] Colorless solid; [Aldrich MSDS]

Physicochemical properties

Melting point
146 · 146-148℃ (acetone )
storage temp.
0 · 0-6°C
form
Crystal
color
White
Merck
13 · 13,3163
BRN
4093655 · 4093655
FDA UNII
6 Y5I03RK7C · 6Y5I03RK7C
EPA Substance Registry System
Difenzoquat methyl sulfate (43222-48-6)
Symbol(GHS)
6 · GHS06,GHS09
Signal word
Danger
Hazard statements
301 · H301+H311-H410
Precautionary statements

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

Warning

H302 (97.6%): Harmful if swallowed [Warning Acute toxicity, oral]

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

Hazard information

Regulatory InformationDifenzoquat methyl sulfate is listed in the dataset of EPA Human Health Benchmarks for Pesticides under the Safe Drinking Water Act (40 eCFR 141)
Other Safety InformationIMAP assessments - 1H-Pyrazolium, 1,2-dimethyl-3,5-diphenyl-, methyl sulfate: Human health tier I assessment
Hazards Summary · 1 item

Causes nucleated red blood cells, changes in serum composition, and changes to the liver in repeated oral dose study of rats; [RTECS] No adverse hematological, clinical chemistry, or histopathological changes observed in 90-day feeding study of dogs; Decreased weight gain was only compound related effect noted in 2-year feeding study of rats; [Reference #1] Toxic by ingestion and skin absorption; May cause irritation; [Aldrich MSDS]

Hazard Classes and Categories · 3 items

Acute Tox. 4 (97.6%)

Acute toxicity - category 4

Acute Tox. 4 *

Toxicology

Treatment · 1 item

If the compound has been ingested, rapid gastric lavage should be performed using 5% sodium bicarbonate. For skin contact, the skin should be washed with soap and water. If the compound has entered the eyes, they should be washed with large quantities of isotonic saline or water. In serious cases, atropine and/or pralidoxime should be administered. Anti-cholinergic drugs work to counteract the effects of excess acetylcholine and reactivate AChE. Atropine can be used as an antidote in conjunction with pralidoxime or other pyridinium oximes (such as trimedoxime or obidoxime), though the use of '-oximes' has been found to be of no benefit, or possibly harmful, in at least two meta-analyses. Atropine is a muscarinic antagonist, and thus blocks the action of acetylcholine peripherally.

Chemistry & industry

Pharmacology

Metabolism/Metabolites · 1 item

Paraoxonase (PON1) is a key enzyme in the metabolism of organophosphates. PON1 can inactivate some organophosphates through hydrolysis. PON1 hydrolyzes the active metabolites in several organophosphates insecticides as well as, nerve agents such as soman, sarin, and VX. The presence of PON1 polymorphisms causes there to be different enzyme levels and catalytic efficiency of this esterase, which in turn suggests that different individuals may be more susceptible to the toxic effect of OP exposure.

Uses & manufacturing

Uses · 3 items

Used as a herbicide and agricultural fungicide; [Merck Index] Used as selective post-emergence herbicide for control of wild oats in barley and wheat; The ion, CAS# 49866-87-7, is of no known commercial use; [Reference #1]

Farming (Pesticides) [Category: Industry]

This is a man-made compound that is used as a pesticide.

Applications · 4 items

DescriptionDifenzoquat metilsulfate is a herbicide mainly used to control wild oats. It is highly soluble in water and has a low volatility. It can be environmentally persistent depending on local conditions. It tends to be moderately toxic to biodiversity. Difenzoquat metilsulfate is also moderately toxic to mammals via the oral route.

UsesDIFENZOQUAT METHYLSULFATE is used to control wild oats in wheat, barley, ax, maize, rye grass, vetches and rye grass crops.

UsesDifenzoquat Methyl Sulfate could have agricultural uses. It could help reduce downward migration of pesticides in soil/turf to allow it to better target pests.

UsesDIFENZOQUAT METHYLSULFATE is Herbicide; agricultural fungicide.

Upstream & downstream products

Upstream raw materials

Related reactions

12 records
New reaction record
HRID 371764 reaction equation
HRID 371764As reactantuspto-grants-1978_05
HRID 426558 reaction equation
HRID 426558As reactantuspto-grants-1979_10
HRID 426564 reaction equation
HRID 426564As productuspto-grants-1979_10
HRID 972037 reaction equation
HRID 972037As productuspto-grants-1979_07
HRID 1457298 reaction equation
HRID 1457298As productuspto-grants-1998_12
HRID 1457299 reaction equation
HRID 1457299As productuspto-grants-1998_12
HRID 1457300 reaction equation
HRID 1457300As productuspto-grants-1998_12
HRID 1457301 reaction equation
HRID 1457301As productuspto-grants-1998_12
Page 1 of 2

Compound notes

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39424
DTXSID
DTXSID6024048
ChEMBL
CHEMBL1867054
UNII
6Y5I03RK7C
EC Number
256-152-5
264 · P264-P270-P273-P280-P301+P310-P302+P352+P312
Hazard Codes
Xn,N
Risk Statements
22 · 22-50/53
Safety Statements
60 · 60-61
RIDADR
2588 · 2588
WGK Germany
3 · 3
RTECS
9820000 · UQ9820000
HazardClass
6.1 · 6.1(b)
PackingGroup
III
Toxicity
50 · LD50 (technical grade) orally in rats: 470 mg/kg; dermally in rabbits: 3540 mg/kg (Shafer)
Health Effects · 1 item

Acute exposure to cholinesterase inhibitors can cause a cholinergic crisis characterized by severe nausea/vomiting, salivation, sweating, bradycardia, hypotension, collapse, and convulsions. Increasing muscle weakness is a possibility and may result in death if respiratory muscles are involved. Accumulation of ACh at motor nerves causes overstimulation of nicotinic expression at the neuromuscular junction. When this occurs symptoms such as muscle weakness, fatigue, muscle cramps, fasciculation, and paralysis can be seen. When there is an accumulation of ACh at autonomic ganglia this causes overstimulation of nicotinic expression in the sympathetic system. Symptoms associated with this are hypertension, and hypoglycemia. Overstimulation of nicotinic acetylcholine receptors in the central nervous system, due to accumulation of ACh, results in anxiety, headache, convulsions, ataxia, depression of respiration and circulation, tremor, general weakness, and potentially coma. When there is expression of muscarinic overstimulation due to excess acetylcholine at muscarinic acetylcholine receptors symptoms of visual disturbances, tightness in chest, wheezing due to bronchoconstriction, increased bronchial secretions, increased salivation, lacrimation, sweating, peristalsis, and urination can occur. Certain reproductive effects in fertility, growth, and development for males and females have been linked specifically to organophosphate pesticide exposure. Most of the research on reproductive effects has been conducted on farmers working with pesticides and insecticdes in rural areas. In females menstrual cycle disturbances, longer pregnancies, spontaneous abortions, stillbirths, and some developmental effects in offspring have been linked to organophosphate pesticide exposure. Prenatal exposure has been linked to impaired fetal growth and development. Neurotoxic effects have also been linked to poisoning with OP pesticides causing four neurotoxic effects in humans: cholinergic syndrome, intermediate syndrome, organophosphate-induced delayed polyneuropathy (OPIDP), and chronic organophosphate-induced neuropsychiatric disorder (COPIND). These syndromes result after acute and chronic exposure to OP pesticides.

Toxicity Summary · 1 item

Difenzoquat metilsulfate is a cholinesterase or acetylcholinesterase (AChE) inhibitor. A cholinesterase inhibitor (or 'anticholinesterase') suppresses the action of acetylcholinesterase. Because of its essential function, chemicals that interfere with the action of acetylcholinesterase are potent neurotoxins, causing excessive salivation and eye-watering in low doses, followed by muscle spasms and ultimately death. Nerve gases and many substances used in insecticides have been shown to act by binding a serine in the active site of acetylcholine esterase, inhibiting the enzyme completely. Acetylcholine esterase breaks down the neurotransmitter acetylcholine, which is released at nerve and muscle junctions, in order to allow the muscle or organ to relax. The result of acetylcholine esterase inhibition is that acetylcholine builds up and continues to act so that any nerve impulses are continually transmitted and muscle contractions do not stop. Among the most common acetylcholinesterase inhibitors are phosphorus-based compounds, which are designed to bind to the active site of the enzyme. The structural requirements are a phosphorus atom bearing two lipophilic groups, a leaving group (such as a halide or thiocyanate), and a terminal oxygen.

Signs and Symptoms · 1 item

Symptoms of low dose exposure include excessive salivation and eye-watering. Acute dose symptoms include severe nausea/vomiting, salivation, sweating, bradycardia, hypotension, collapse, and convulsions. Increasing muscle weakness is a possibility and may result in death if respiratory muscles are involved. Hypertension, hypoglycemia, anxiety, headache, tremor and ataxia may also result.

EPA IRIS Information · 2 items

Difenzoquat

8 x 10 ^-2 mg/kg-day

Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).
Toxicity DataLC50 (rat) = 500 mg/m3
RAIS Toxicity Values · 2 items

0.083

OPP

EPA Human Health Benchmarks for Pesticides · 5 items

Difenzoquat methyl sulfate

0.083

490

General Population

Human Health Benchmarks for Pesticides - 2021 Update

Hazard Quotient Level 0.1 or Cancer Risk Level 1E-06 · 6 items

5.20e+03

6.80e+04

1.70e+03

5.00e+00

2.60e+02

8.30e-02

Hazard Quotient Level 3 or Cancer Risk Level 1E-04 · 6 items

1.60e+04

2.00e+05

5.00e+03

5.00e+00

8.30e-02

Volatile

Safety data

wgk
3
rtecs
UQ9820000
ridadr
2588
Toxicity
LD50 (technical grade) orally in rats: 470 mg/kg; dermally in rabbits: 3540 mg/kg (Shafer)
risk_code
22-50/53
Signal word
Danger
Symbol(GHS)
GHS06,GHS09
hazard_code
Xn,N
safety_code
60-61
hazard_class
6.1(b)
packing_group
III
Hazard statements
H301+H311-H410
Precautionary statements
P264-P270-P273-P280-P301+P310-P302+P352+P312
Xylene1,3-Diphenylacetone5-Methyl-2-phenyl-1,2-dihydropyrazol-3-oneDimethyl esterHydrogen peroxideHydrazine hydrateAcetophenoneExpoxideDifenzoquatAluminum chlorideBenzaldehydePara tolueneEthanol 95%Sulphur3,5-Diphenylpyrazole