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Carboxin is a heterocyclic fungicide with systemic effect. The pure product is white needle-like crystals.
Carboxin is hardly soluble in water, but soluble in organic solvents such as methanol, acetone and benzene.
Carboxin is easy to decompose and become invalid in case of alkaline substances.
CAS No.: 5234-68-4
Molecular Formula: C12H13NO2S
Molecular Weight: 235.30 g/mol
COD Number: 2242734
MDL Number: MFCD00055403
CBNumber: CB9267538
MOL File: 5234-68-4.mol
Synonyms: 5,6-Dihydro-2-methyl-N-phenyl-1,4-oxathiin-3-carboxamide, 2-Methyl-N-phenyl-5,6-dihydro-1,4-oxathiine-3-carboxamide, Carbathiin, Carboxine, DCMO, Dmoc, Fenoxan
Description
Carboxin is an anilide obtained by formal condensation of the amino group of aniline with the carboxy group of 2-methyl-5,6-dihydro-1,4-oxathiine-3-carboxylic acid.
A fungicide for control of bunts and smuts that is normally used as a seed treatment.
Carboxin has a role as an EC 1.3.5.1 [succinate dehydrogenase (quinone)] inhibitor and an antifungal agrochemical.
Carboxin is an anilide, a secondary carboxamide, an oxacycle, an organosulfur heterocyclic compound, an enamide and an anilide fungicide.
Carboxin is a systemic anilide and oxathiin fungicide primarily used as a seed treatment to control smuts, rusts, and rot diseases in cereals, vegetables, and other crops.
Carboxin works by inhibiting mitochondrial complex III (succinate dehydrogenase) to disrupt fungal energy production.
Carboxin is a white crystalline solid.Molecular weight=235.32; Freezing/Meltingpoint=91.5-95℃ (depending on crystal structure); Vaporpressure=1.78 x 10 2 7 mmHg. Practically insoluble inwater; solubility=25 mg/L; 0.15 g/L at 20℃.
The dosage forms are wettable powder, emulsifiable concentrate and so on.
Carboxin is mainly used for the prevention and treatment of sorghum head smut and other cereal smut, as well as the prevention and treatment of wheat rust, cotton grass disease, and millet disease.
Low toxicity to humans and animals.
Chemical and Physical Properties
Formula: C₁₂H₁₃NO₂SAppearance: White needle-like crystals
Solubility: Hard to dissolve in water; soluble in organic solvents like acetone and methanol
Stability: Breaks down easily when exposed to alkaline substances
Properties
Melting point: 91.1-91.7°C
Boiling point: 420.6±45.0 °C(Predicted)
Density: 1.45
vapor pressure: 2.5 x 10-5 Pa (25 °C)
refractive index: 1.6000 (estimate)
Flash point: 100 °C
storage temp.: Sealed in dry,2-8°C
solubility: Chloroform (Slightly), Methanol (Slightly)
pka: 14.31±0.70(Predicted)
form: Crystals
color: White
Water Solubility: 10.095 g/100 mL
Merck: 13,1837
BRN: 983249
Henry's Law Constant: 3.1×104 mol/(m3Pa) at 25℃, Duchowicz et al. (2020)
Major Application: agriculture
environmental
InChI: 1S/C12H13NO2S/c1-9-11(16-8-7-15-9)12(14)13-10-5-3-2-4-6-10/h2-6H,7-8H2,1H3,(H,13,14)
InChIKey: GYSSRZJIHXQEHQ-UHFFFAOYSA-N
LogP: 2.140
Chemical Properties
Carboxin is a white crystalline solid
Uses
Carboxine is an fungicide used for the control of fruit rot of custard apple.
Systemic plant fungicide.
Carboxin is used as a seed treatment for cereals and as a seedling treatment on many cereals, beans, and vegetable crops and cotton.
Carboxin is also used for the treatment of turf.
Definition
ChEBI: An anilide obtained by formal condensation of the amino group of aniline with the carboxy group of 2-methyl-5,6-dihydro-1,4-oxathiine-3-carboxylic acid.
A fungicide for control of bunts and smuts normally that is normally used as a seed treatment.
Production Methods
Carboxin is synthesised through a multi-step chemical process that begins with ethyl 2-chloroacetoacetate reacting with 2-mercaptoethanol in the presence of a base.
This forms a key intermediate that undergoes cyclization and dehydration under acidic conditions to yield the 1,4-oxathiine heterocycle.
The resulting ethyl ester is then converted into a carboxylic acid, which is subsequently transformed into an acid chloride.
This intermediate is reacted with aniline under standard amidation conditions to produce carboxin in high yield.
General Description
Off-white crystals. Systemic fungicide and seed protectant.
Agricultural Uses
Fungicide: Carboxin is a General Use Pesticide (GUP) and is used as a seed protectant.
Carboxin is often used in combination with other fungicides such as thiram or captan.
Carboxin is a systemic anilide fungicide.
Carboxin is used as a seed treatment for control of smut, rot, and blight on barley, oats, rice, cotton, vegetables, corn and wheat.
Carboxin is also used to control fairy rings on turf grass.
Carboxin may be used to prevent the formation of these diseases or may be used to cure existing plant diseases.
Also used as a wood preservative.
Trade name
CADAN®; CARBOXIN OXATHION PESTICIDE®; CASWELL No. 165 A®; D-735®; F-735®; FLO PRO V SEED PROTECTANT®[C]; KEMIKAR®; OXALIN®; PADAN®; SANVEX®; THIOBEL®; VEGETOX®; VITAFLO®; VITAVAX® 200FF; V 4X®
Mechanism of action
Systemic, inhibits mitochondrial function.
Succinate Dehydrogenase Inhibitor.
Safety Profile
Poison by ingestion. Moderately toxic by skin contact and possibly other routes. Mutation data reported.
When heated to decomposition Carboxin emits very toxic fumes of NOx and SOx.
Potential Exposure
A potential danger to those involved in the production, Formulation and application of this systemic fungicide, seed protectant and wood preservative
First aid
If this chemical gets into the eyes, remove anycontact lenses at once and irrigate immediately for at least15 min, occasionally lifting upper and lower lids.
Seek medical attention immediately.
If this chemical contacts theskin, remove contaminated clothing and wash immediatelywith soap and water.
Seek medical attention immediately.
Ifthis chemical has been inhaled, remove from exposure,begin rescue breathing (using universal precautions, including resuscitation mask) if breathing has stopped and CPR ifheart action has stopped.
Transfer promptly to a medicalfacility.
When this chemical has been swallowed, get medical attention.
Give large quantities of water and inducevomiting.
Do not make an unconscious person vomit.
Environmental Fate
Biological.
The sulfoxidation of carboxin to carboxin sulfoxide by the fungus Ustilago maydis was reported by Bollag and Liu (1990).
Soil. Carboxin oxidized in soil forming carboxin sulfoxide.
The half-life in soil was reported to be 24 hours (Worthing and Hance, 1991).
Plant.
In plants (barley, cotton and wheat) and water, carboxin oxidizes to the corresponding sulfoxide (Worthing and Hance, 1991).
Metabolic pathway
Carboxin is a systemic fungicide which is very stable to hydrolysis but is readily oxidised at sulfur to a sulfoxide and a sulfone.
The latter, oxycarboxin, is itself a commercial fungicide.
Metabolism is mainly by oxidation at sulfur in soil, plants and animals but hydroxylation of the phenyl ring is also important in animals.
Hydrolysis has been convincingly demonstrated only in plants (peanut).
storage
Color Code—Blue: Health Hazard/Poison: Store ina secure poison location.
Prior to working with carboxin youshould be trained on its proper handling and storage.
Storein tightly closed containers in a cool, well-ventilated area
Shipping
UN2588 Pesticides, solid, toxic, Hazard Class: 6.1; Labels: 6.1-Poisonous materials, Technical Name Required.
Degradation
Carboxin is stable to hydrolysis (25 °C) at pH 5,7 and 9.
Measurable rates are seen only at higher pH and occur by nucleophilic attack by hydroxyl ion at carbonyl.
The half-life in 0.5 N NaOH is 107 days.
Thus chemical hydrolysis is not expected to be significant under environmental conditions (El-Dib and Aly, 1976).
The compound is very labile to aqueous photolysis with a DT50 of <3 hours (PM).
Incompatibilities
Incompatible with oxidizers (chlorates, nitrates, peroxides, permanganates, perchlorates, chlorine, bromine, fluorine, etc.); contact may cause fires or explosions.
Keep away from alkaline materials, strong bases, strong acids, oxoacids, epoxides. Avoid heat and humidity.
Thermal decomposition products may include cyanide gas and cyanide salts.
Waste Disposal
Dissolve or mix the material with a combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber.
All federal, state, and local environmental regulations must be observed.
Pesticide Type
Fungicide
Production method
The α-chloroacetoacetanilide is obtained by the reaction of acetoacetanilide and sulfuryl chloride, which is then obtained by condensation with mercaptoethanol.
Raw material consumption quota: acetoacetanilide 1090kg/t, sulfuryl chloride 880kg/t, mercaptoethanol (>95%) 490kg/t, p-toluenesulfonic acid 30kg/t.
Uses
This product is effective against Rhizoctonia, and is especially suitable for seed treatment of cotton, peanuts, vegetables and sugar beets.
Carboxin has a growth stimulating effect on crops.
Carboxin is low-toxic to humans and animals, but Carboxin should not be in contact with eyes.
The seeds that have been treated with wilkins are not edible or used for feeding. Carboxin is a selective systemic fungicide.
Carboxin is mainly used to prevent rust and smut (ear) disease caused by rust and smut fungus on various crops.
Carboxin is also effective against cotton wilt and verticillium wilt.
Such as sorghum loose smut, head smut, corn head smut, wheat smut, wheat rust, millet smut, and cotton seedling diseases.
Agricultural Uses
Seed treatment: Protects seeds and seedlings against smut, blight, and rot.
Target crops: Used on wheat, barley, corn, cotton, rice, and soybeans.
Common trade name: Vitavax
Suitable crops
Wheat, barley, oats, rice, cotton, peanuts, soybeans, vegetables, corn, sorghum and many other crops and lawns.
20% Carboxin EC 100 times liquid may have slight harm to wheat.
The seeds treated with the medicament cannot be eaten or used as feed.
Carboxin can also be used for foliar spraying to prevent rust diseases such as wheat, beans, pears, cotton seedling diseases, verticillium wilt, and wilt.
Carboxin can also be used as a wood preservati
