5234-68-4 Usage
Chemical Properties
Carboxin is a white crystalline solid
Uses
Different sources of media describe the Uses of 5234-68-4 differently. You can refer to the following data:
1. Carboxine is an fungicide used for the control of fruit rot of custard apple.
2. Systemic plant fungicide.
3. Carboxin is used as a seed treatment for cereals and as a seedling
treatment on many cereals, beans, and vegetable crops and cotton. It 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.
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. 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?
Safety Profile
Poison by ingestion.
Moderately toxic by skin contact and
possibly other routes. Mutation data
reported. When heated to decomposition it
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
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).
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.
Check Digit Verification of cas no
The CAS Registry Mumber 5234-68-4 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 5,2,3 and 4 respectively; the second part has 2 digits, 6 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 5234-68:
(6*5)+(5*2)+(4*3)+(3*4)+(2*6)+(1*8)=84
84 % 10 = 4
So 5234-68-4 is a valid CAS Registry Number.
InChI:InChI=1/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)
5234-68-4Relevant articles and documents
Addition-substitution reactions of 2-thio-3-chloroacrylamides with carbon, nitrogen, oxygen, sulfur and selenium nucleophiles
Kissane, Marie,Murphy, Maureen,O'Brien, Elisabeth,Chopra, Jay,Murphy, Linda,Collins, Stuart G.,Lawrence, Simon E.,Maguire, Anita R.
supporting information; experimental part, p. 2452 - 2472 (2011/05/11)
Synthetically versatile conjugate addition of a range of carbon, nitrogen, oxygen, sulfur and selenium nucleophiles to the highly functionalised 2-thio-3-chloroacrylamides is described. The stereochemical and synthetic features of this transformation are discussed in detail. In most instances, the nucleophile replaces the chloro substituent with retention of stereochemistry. With the oxygen nucleophiles, a second addition can occur leading to acetals, while with the nitrogen nucleophiles, E-Z isomerism occurs in the resulting enamine derivatives. The ratio of the E/Z isomers can be rationalised on the basis of the substituent and the level of oxidation.
CONVERSION OF DIHYDRO-1,4-OXATHIIN-3-CARBOXAMIDE TO THE ISOMERIC DIHYDRO-1,4-OXATHIIN-2-CARBOXAMIDE
Hahn, Hoh-Gyu,Chang, Kee-Hyuk,Lee, Wha Suk
, p. 921 - 931 (2007/10/02)
The preparation of isomeric dihydro-1,4-oxathiin (3) from the dihydro-1,4-oxathin (1) via dichloro-1,4-oxathiane (4) is described.Chlorination of 1 followed by treatment of the resulting dichloride (4) with aqueous acetone gave dihydroxy-1,4-oxathiin (5).The solvolysis to produce intermediate chlorohydrin (11) was favored relative to elimination reaction to give exomethylene compound (8).Dehydration of 5 followed by reduction afforded α-hydroxy-1,3-oxathiolane (2) which is a key compound to prepare the isomeric dihydro-1,4-oxathiin (3).The reason for more facile displacement of chlorine at C-2 in comparison with that at C-4 in 4 was also discussed.
Studies on the Preparation of Dihydro-1,4-oxathiines. Computer-Assisted Evaluation of the Results of Retrosynthetic Analysis Verified by Synthetic Experiments and By-Product Analyses. Synthetic Pathways Involving α-Sulfenylated Ketones and 1,3-Oxathiolanes of α-Halo and α-Hydroxy K...
Nevalainen, Vesa,Pohjala, Esko,Maelkoenen, Pentti,Hukkanen, Heikki
, p. 591 - 602 (2007/10/02)
The preparation of 2- and 2,3-substituted 5,6-dihydro-1,4-oxathiines has been studied by computer simulation and by experiment.Three major synthetic pathways, involving 2-(1-hydroxyalkyl)-1,3-oxathiolanes, 2-(1-haloalkyl)-1,3-oxathiolanes, 2-hydroxyethylthiomethyl ketones, methanesulfonates of 2-hydroxyethylthiomethyl ketones and 2-choroethylthiomethyl ketones as intermediates, were evaluated, by running the program CAMEO, and by experiment.The results of the two approaches were compared and the major by-products of the reactions were identified by GLC/MS.