Name | Pyribenzoxim |
Synonyms | Pyanchor LGC 40863 Pyribenzoxim pyribenzoxim PyribenzoxiM(Pyanchor) O-(2,6-Bis(4,6-dimethoxypyrimidin-2-yloxy)benzoyl)oxime benzophenone Benzophenone O-[2,6-bis[(4,6-dimethoxy-2- pyrimidyl)oxy]benzoyl]oxime Benzophenone O-(2,6-bis((4,6-dimethoxypyrimidin-2-yl)oxy)benzoyl) oxime {2,6-bis[(4,6-dimethoxypyrimidin-2-yl)oxy]phenyl}{[(diphenylmethylidene)amino]oxy}methanone |
CAS | 168088-61-7 |
EINECS | 605-503-4 |
InChI | InChI=1/C32H27N5O8/c1-39-24-18-25(40-2)34-31(33-24)43-22-16-11-17-23(44-32-35-26(41-3)19-27(36-32)42-4)28(22)30(38)45-37-29(20-12-7-5-8-13-20)21-14-9-6-10-15-21/h5-19H,1-4H3 |
Molecular Formula | C32H27N5O8 |
Molar Mass | 609.59 |
Density | 1.30±0.1 g/cm3(Predicted) |
Melting Point | 129 °C |
Boling Point | 810.8±75.0 °C(Predicted) |
Flash Point | 444.1°C |
Solubility | DMSO (Slightly, Heated), Methanol (Slightly, Heated) |
Vapor Presure | 2.4E-26mmHg at 25°C |
Appearance | Solid |
Color | White to Off-White |
pKa | -0.02±0.30(Predicted) |
Storage Condition | 2-8°C |
Refractive Index | 1.612 |
Physical and Chemical Properties | pure as a white solid. m. P. 128-130 ° C., vapor pressure <7.4 × 10-6Pa. The solubility in water was 3.5mg/L at 25 °c. Field half-life was 7d. |
Use | Novel oxime-ester compounds, broad-spectrum selective post-emergence herbicides. The mechanism of action is similar to sulfonylureas and imidazolidinone herbicides, which are acetolactate synthase (ALS) inhibitors. For Rice, common wheat, Zoysia has selective super-efficient herbicidal activity after Bud, no herbicidal activity before Bud, for the control of Humulus scandens, Meigan, all kinds of Gramineae weeds and broad-leaf miscellaneous diseases, such as Polygonum morselum, have outstanding effects and are safe for rice and common wheat. The herbicidal speed of the pesticide is slow, and the growth of weeds can be inhibited after application, but it must die after 2 weeks. The drug use was moderately wide, and it was effective for 1.5~6.5 leaf stage of Humulus scandens. In the 2.5~3.5 leaf stage, the dose of 10g/hm2 was up to 100%, and the dose of 3.5~4.5 was increased to 20g/hm2, which was up to 100%. |
toxicity | acute oral LD50>5000 mg/kg in rats and acute percutaneous LD50>2000 mg/kg in mice. No irritation to eyes and skin. No teratogenic effect on chromosomes, Ames test was negative. For Daphnia LC50>100mg/L(48h) and algae EC50>100mg/L(96h). |
uses | novel oxime ester compounds, broad-spectrum selective post-bud herbicide. The mechanism of action is similar to sulfonylurea and imidazolidone herbicides, and they are all acetolactate synthase (ALS) inhibitors. It has selective and ultra-efficient post-bud weeding activity for rice, common wheat, and Zoysia, and has no pre-bud weeding activity. It is used to control various gramineous weeds and broad-leaved weeds such as barnyard grass, big spike kanmai Niang, and Polygonum hydropiper. The effect is outstanding, and it is safe for rice and common wheat. The herbicidal speed of the agent is slow, and it can inhibit the growth of weeds after application, but it must die after 2 weeks. The drug is moderately wide and effective for barnyard grass at 1.5 to 6.5 leaf stages. In the 2.5~3.5 leaf stage, the dose of 10g/hm2 can reach 100% control. The dose of 3.5~4.5 leaf stage is increased to 20g/hm2, which can reach 100% control. |
Production method | Acylation of 2,6-dihydroxybenzoic acid (1) to 2,6-diacetyloxybenzoic acid (2). Subsequently, it is activated by thionyl chloride and esterified with dibenzophenone oxime (3) at low temperature. The product uses DMF as a solvent in the presence of potassium carbonate and reacts with 4, 6-dimethoxy-2-methylsulfonylpyrimidine to obtain the final product pyrimidine oxime ether. Operation method: weigh 1.5g(10mmol) of 2,6-dihydroxybenzoic acid and 10mL(0.1mol) of acetic anhydride, and heat to 80 ℃ for stirring for 3 hours. The reactants were poured into ice water for 6h, filtered and dried naturally to obtain 2.1g of 2, 6-diacetyloxybenzoic acid white solid (2). Without purification, the above white solid (2) is dissolved in 5mL of dichloromethane, 1.5mL of thionyl chloride (2.0mmol) dichloromethane (5mL) solution is added dropwise at 0 ℃, and the product is steamed by reacting for 2h at room temperature. The obtained product was dissolved in dichloromethane (5mL), 2.0g(10mmol) of dichloromethane solution was added dropwise at -20 ℃, and reacted at -20 ℃ for 4 hours. The reactants are poured into water, extracted with ether, washed with sodium bicarbonate aqueous solution, dried with anhydrous magnesium sulfate, and purified by silica gel column chromatography after desolysis to obtain 2.7g of product (4). Next, 4, 6-dimethoxy-2-methylsulfonylpyrimidine (5)2.1g (9.6mmol) was added in batches to a mixture of compound (4)2.0g(4.8mmol) and potassium carbonate 1.0g (7.2mmol) of DMF (5mL), heated to 80°C, and reacted for 15h. The reaction mixture is diluted with water (10mL), ether extraction, sodium carbonate aqueous solution washing, anhydrous magnesium sulfate drying. Desolubilization, and then silica gel column chromatography separation and purification of pyrimidine oxime ether 1.5g. M. p.128 ~ 130 ℃. |