Uses
Carboxine is an fungicide used for the control of fruit rot of custard apple.
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.
Uses
Systemic plant fungicide.
General Description
Off-white crystals. Systemic fungicide and seed protectant.
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 any
contact lenses at once and irrigate immediately for at least
15 minutes, occasionally lifting upper and lower lids. Seek
medical attention immediately. If this chemical contacts the
skin, remove contaminated clothing and wash immediately
with soap and water. Seek medical attention immediately.
If this chemical has been inhaled, remove from exposure,
begin rescue breathing (using universal precautions, including resuscitation mask) if breathing has stopped and CPR if
heart action has stopped. Transfer promptly to a medical
facility. When this chemical has been swallowed, get medical attention. Give large quantities of water and induce
vomiting. Do not make an unconscious person vomit.
Shipping
UN2588 Pesticides, solid, toxic, Hazard Class: 6.1;
Labels: 6.1-Poisonous materials, Technical Name Required.
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.
Description
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℃.
Chemical Properties
Carboxin is a white crystalline solid
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.
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.
Agricultural Uses
Fungicide: Carboxin is a General Use Pesticide (GUP) and is used as a seed protectant. It is often used in combination with other fungicides such as thiram or captan. Carboxin is a systemic anilide fungicide. It is used as a seed treatment for control of smut, rot, and blight on barley, oats, rice, cotton, vegetables, corn and wheat. It 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.
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
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).
