101205-02-1

Basic information

• Product Name: CYCLOXYDIM
• Synonyms: (+-)-2-(1-(ethoxyimino)butyl)-3-hydroxy-5-thian-3-cyclohex-2-enone;2-(1-(ethoxyimino)butyl)-3-hydroxy-5-(tetrahydro-2h-thiopyran-3-yl)-2-cycloh;2-cyclohexen-1-one,2-(1-(ethoxyimino)butyl)-3-hydroxy-5-(tetrahydro-2h-thiopyr;2-cyclohexen-1-one,2-[1-(ethoxyimino)butyl]-3-hydroxy-5-(tetrahydro-2h-thiopyr;an-3-yl)-;cycloxydime;exen-1-one;STRATOS
• CAS NO: 101205-02-1
• Molecular Formula: C17H27NO3S
• Molecular Weight: 325.47
• Product Categories: Cyclohexene oxime;Alpha sort;C;CAlphabetic;CO - CZPesticides&Metabolites;Herbicides;Pesticides&Metabolites
• Mol File: 101205-02-1.mol
• Article Data: 14

Chemical Properties

• Melting Point: 41℃
• Boiling Point: 450.2°Cat760mmHg
• Flash Point: 226°C
• Appearance: /
• Density: 1.21
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.582
• Storage Temp.: -20°C
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: 4.32±0.25(Predicted)
• Stability: Hygroscopic
• BRN: 8436332
• CAS DataBase Reference: CYCLOXYDIM(CAS DataBase Reference)
• NIST Chemistry Reference: CYCLOXYDIM(101205-02-1)
• EPA Substance Registry System: CYCLOXYDIM(101205-02-1)

Safety Data

• Hazard Codes: F,Xi,Xn
• Statements: 11-36-66-67-63
• Safety Statements: 9-16-26
• RIDADR: UN 1090 3/PG 2
• WGK Germany: 3
• RTECS: GW6425000
• Hazardous Substances Data: 101205-02-1(Hazardous Substances Data)

Usage

Uses

Cycloxydim is a cyclohexene oxime herbicide that is used for the control of grass weeds of many agricultural and horticultural broad-leaved crops.

Definition

ChEBI: A beta-diketone that is cyclohexa-1,3-dione which is substituted at position 2 by an N-ethoxybutanimidoyl group and at position 5 by a tetrahydro-2H-thiopyran-3-yl group. A systemic herbicide effective against grasses, it is used in the cultivation of a variety of crops, including oil seed rape and potatoes.

Metabolic pathway

Cycloxydim is rapidly metabolized in soybean plants, and four series of different types of metabolite in either free or conjugated form are identified. Transformation products are formed by chemical and/or enzymatic reactions involving a range of oxidation, a rearrangement, and cleavage of the cyclohexanone ring or ethoxyimino side chain.

InChI:InChI=1/C17H27NO3S/c1-3-6-14(18-21-4-2)17-15(19)9-13(10-16(17)20)12-7-5-8-22-11-12/h12-13,19H,3-11H2,1-2H3/b18-14+

Relevant articles and documents

Photolysis of cycloxydim, a cyclohexanedione oxime herbicide. Detection, characterization and reactivity of the iminyl radical

Cyclohexanedione oxime herbicides have been reported to be readily photodegraded in the environment but the reaction mechanism has never been studied in detail. Here we investigated the photolysis of cycloxydim (CD) in acetonitrile and water, solvents in which CD is present as two distinct tautomeric forms: keto form in water and enol form with an intramolecular hydrogen bond between the enolic proton and the nitrogen atom of the oxime in acetonitrile O-H...N. CD (E isomer) undergoes photoisomerization in water but not in acetonitrile. This difference is attributed to the inhibiting effect of the intramolecular hydrogen bond existing in acetonitrile. In both solvents, irradiation of CD leads to the cleavage of the N-O bond as evidenced by the imine formation. The iminyl radical could be detected in acetonitrile by nanosecond laser-flash photolysis (λmax = 280, 320 and 480 nm, τ ～ 100 μs). This radical is unreactive toward oxygen but readily abstracts an H atom from methanol (k = 1.8 × 105 M-1 s-1). Quantum calculations confirm the assignment of the transient species to the iminyl radical by showing that (i) the most stable structure of the iminyl carries a large spin density on the ring carbon and on the nitrogen atoms, (ii) the enolic H atom is transferred to the nitrogen atom and (iii) the intramolecular hydrogen bond O...H-N is responsible for both the iminyl long wavelength absorption and its high hydrogen abstraction reactivity.

LIQUID FORMULATIONS

The present invention relates to a liquid formulation comprising a) agrochemically active salts of 2-iodo-N-[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)carbamoyl]benzenesulfonamide, and b) one or more non-polar organic solvents selected from the group of the C6-C16-aromatics mixture the Solvesso series (Exxon) and/or the Caromax series (Carless), and also ?optionally further non-polar organic solvents. The liquid formulation is suitable for crop protection.

Herbicidal composition

The present invention relates to a herbicidal composition, comprising A) one or more compounds of the formula (I) 1in which Hal1 and Hal2 are identical or different halogen atoms, R1 is H, a cation or a C1-C20-carbon-containing radical and B) one or more surfactants, comprising as structural element at least 12 alkylene oxide units.