| Identification | Back Directory | [Name]
1,5-dimethyl-6-thioxo-3-(2,2,7-trifluoro-3-oxo-4-(prop-2-ynyl)-3,4-dihydro-2H-benzo[b][1,4]oxazin-6-yl)-1,3,5-triazinane-2,4-dione | [CAS]
1258836-72-4 | [Synonyms]
Trifludimoxazin
1,5-dimethyl-6-thioxo-3-(2,2,7-trifluoro-3-oxo-4-(prop-2-ynyl)-3,4-dihydro-2H-benzo[b][1,4]oxazin-6-yl)-1,3,5-triazinane-2,4-dione
1,3,5-Triazine-2,4(1H,3H)-dione, dihydro-1,5-dimethyl-6-thioxo-3-[2,2,7-trifluoro-3,4-dihydro-3-oxo-4-(2-propyn-1-yl)-2H-1,4-benzoxazin-6-yl]- | [Molecular Formula]
C16H11F3N4O4S | [MOL File]
1258836-72-4.mol | [Molecular Weight]
412.34 |
| Chemical Properties | Back Directory | [Boiling point ]
555.1±60.0 °C(Predicted) | [density ]
1.69±0.1 g/cm3(Predicted) | [form ]
Solid | [pka]
-2.44±0.20(Predicted) | [color ]
Light yellow to khaki | [EPA Substance Registry System]
1,3,5-Triazine-2,4(1H,3H)-dione, dihydro-1,5-dimethyl-6-thioxo-3-[2,2,7-trifluoro-3,4-dihydro-3-oxo-4-(2-propyn-1-yl)-2H-1,4-benzoxazin-6-yl]- (1258836-72-4) |
| Hazard Information | Back Directory | [Description]
A fast-acting herbicide used to control broadleaved and grass weeds. Trifludimoxazin has a low aqueous solubility and a low volatility. It is not expected to be persistent in soils. It demonstrates a low toxicity to most fauna and flora. Trifludimoxazin has a low mammalian toxicity if ingested and no serious health implications have been identified. | [Uses]
Trifludimoxazin is a protoporphyrinogen oxidase inhibiting (PPO) herbicide[1]. Trifludimoxazin is a click chemistry reagent, it contains an Alkyne group and can undergo copper-catalyzed azide-alkyne cycloaddition (CuAAc) with molecules containing Azide groups. | [Definition]
ChEBI:Trifludimoxazin is a member of the class of 1,3,5-triazinanes that is 6-sulfanylidene-1,3,5-triazinane-2,4-dione in which the hydrogens attached to the nitrogens adjacent to the thioxo group have been replace by methyl groups and in which the hydrogen attached to the remaining nitrogen has replaced by a 2,2,7-trifluoro-3-oxo-4-(prop-2-yn-1-yl)-3,4-dihydro-1,4-benzoxazin-6-yl group. A protoporphyrinogen oxidase inhibitor, it is used as a herbicide. It has a role as a herbicide, an EC 1.3.3.4 (protoporphyrinogen oxidase) inhibitor and an agrochemical. It is a benzoxazine, a member of 1,3,5-triazinanes and an organofluorine compound. | [Synthesis]
374.6 g (2.2647 mol) 1,1'-carbonyldiimidazole (98%), 76.4 g (0.7549 mol) triethyamine and 2437 g ethyl acetate were initially charged at 20°C in a stirred vessel. 200 g (0.7549 mol) 6- amino-2,2,7-trifluoro-4-prop-2-yny4H-benzo[1,4]oxazin-3-one (96,7%) were added in portions. The reaction mixture was heated to 55°C At this temperature 95.4 g (0,9064 mol) N,N'-dimethylthiourea (99%) were added. The reaction mixture was stirred at 75-77°C for 25 hours and then poured to a mixture of 2680 ml ice/water and 460 ml hydrochloric acid (32%). The phases were separated and the aqueous phase was extracted twice with 775 ml ethyl acetate. The combined organic phases were dried with Na2SO4 and concentrated to yield 322.9 g. The residue was dissolved in 5970 ml methanol at 65°C 5600 ml methanol were disted off and the remaining suspension was cooled to 0°C. The solid was filtered off and washed with 100 ml cold methanol. The wet solid was dried in a vacuum cabinet at 50°C/10mbar over 24 hours. the desired product trifludimoxazin (determined by quant. HPLC; HPLCmethod A) were isolated. yield 271.0 g, 86.9%.[2]
| [References]
[1] Asher, Brady Scott, et al. Vertical mobility, soil adsorption, and cotton tolerance to three Protoporphyrinogen oxidase (PPO) inhibiting herbicides in three West Texas soils. Texas tech university. |
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