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Dichloro-acetyl benzo-oxazine type herbicide safener and synthetic method thereof

A technology of dichloroacetylbenzene and synthetic methods, which is applied in botany equipment and methods, biocides, animal repellents, etc., can solve the problems of high reaction temperature, long reaction time, high cost of raw materials, etc., and achieve mild reaction conditions , high promotional value and cheap raw materials

Inactive Publication Date: 2009-12-09
NORTHEAST AGRICULTURAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there are shortcomings such as high raw material cost, long reaction time, complicated operation, high reaction temperature, many by-products, and serious environmental pollution in the technology of synthesizing the above-mentioned various compounds, and there is no safener developed for the action characteristics of a class of herbicides
At present, there is no report on the synthesis and biological activity of dichloroacetyl benzoxazine compounds

Method used

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  • Dichloro-acetyl benzo-oxazine type herbicide safener and synthetic method thereof
  • Dichloro-acetyl benzo-oxazine type herbicide safener and synthetic method thereof
  • Dichloro-acetyl benzo-oxazine type herbicide safener and synthetic method thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0018] The synthetic route of 4-dichloroacetyl-3,4-dihydro-2H-1,4-benzoxazine is:

[0019]

[0020] Preparation:

[0021] 2-Aminophenol (0.027mol), dimethyl sulfoxide (40mL), and anhydrous potassium carbonate (0.054mol) were mixed, the temperature was raised to 80°C, and 1,2-dibromoethane (0.027mol) was added dropwise to the solution , stirred and refluxed for 6-8h, cooled, added 50mL of water to the system, extracted with ethyl acetate, dried the organic layer with anhydrous calcium chloride, distilled off ethyl acetate, separated by silica gel column chromatography (eluent: ethyl acetate : petroleum ether=1:6), a red oily product was obtained with a yield of 52.79%.

[0022] Using N,N-dimethylacetamide (10mL) as a solvent, add 300mg of the above intermediate, at 20-30°C, slowly add an appropriate amount of dichloroacetyl chloride dropwise, after the drop is complete, continue stirring for 1-2h, and add water to obtain White solid product, recrystallized from ethyl aceta...

Embodiment 2

[0024] The synthetic route of 4-dichloroacetyl-3,4-dihydro-6-chloro-2H-1,4-benzoxazine is:

[0025]

[0026] Preparation:

[0027] Preparation of 2-nitro-4-chlorophenol: At 18°C, slowly add 65% nitric acid (2.82mL, 40mmol) in glacial acetic acid (8mL) solution dropwise (6 mL) solution. After about 10 minutes, an orange-yellow solid appeared, and the dripping was completed in 0.5 hours, and the stirring was continued for 0.5 hours. The reaction mixture was slowly poured into ice water (100 mL) and stirring was continued for 0.5 h. Filter, wash the filter cake with water until the water phase is neutral, and dry the filter cake in the air to obtain 2-nitro-4-chlorophenol as a yellow solid. The product weighs 6.66g, the yield is 96%, m.p.87-88°C.

[0028] Preparation of 2-amino-4-chlorophenol: Add iron powder (3g), water (20mL), absolute ethanol (20mL), hydrochloric acid (0.6mL), NH 4 Cl (0.15g), add 2-3 drops of glacial acetic acid dropwise to the system, raise the temper...

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Abstract

The invention relates to a dichloro-acetyl benzo-oxazine type herbicide safener and a synthetic method thereof, belonging to an organic synthesis technique. The basic structure of the dichloro-acetyl benzo-oxazine type herbicide safener is disclosed in the right formula; in the formula, R is H, halogen or an alkyl substituting radical; The synthetic method comprises the following steps: (1), substituent amino phenol is used as a raw material, a solvent is added, and anhydrous potassium carbonate is used as catalyst; (2), the system is heated up to 70 to 100 DEG C, 1, 2-ethylene dibromide is dropped into the solution, and stirring and circumfluence are carried out for 6 to 8 hours; (3), the mixture is cooled, added with 50mL of water, processed, then extracted by using ethyl acetate and dried by using calcium chloride, distillation is carried out to obtain the ethyl acetate, and a red oily intermediate is obtained by carrying out chromatographic separation on a coarse product by a silica gel column; (4), the solvent is added into the intermediate, the temperature of the system is controlled below 10 to 40 DEG C, an amount of dichloroacetyl chloride is slowly dropped into the mixture, the mixture is stirred for 1 to 2 hours after dropping, distillation is carried out on the mixture to obtain the solvent, and the final product is obtained by a recrystallization method by separation and purification; and the method features easy acquirement of the raw materials, simple operation, low production cost and no environmental pollution.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis and pesticide synthesis, and specifically relates to two dichloroacetyl benzoxazine herbicide safeners and a synthesis method thereof. Background technique [0002] With the widespread use of amide herbicides such as acetochlor and metolachlor, the problem of phytotoxicity is becoming more and more serious, especially when the dosage is too large and the climate conditions of continuous low temperature, rainy and high humidity are encountered after application. It is prone to phytotoxicity and seriously affects the growth of crops. Herbicide safeners selectively protect crops from herbicide damage without affecting the activity of herbicides on target weeds, thereby enhancing crop tolerance to herbicides and increasing the safety of herbicides on crops . Using safener to solve the problem of herbicide injury is an effective means. In the past ten years, the development of safeners has...

Claims

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Application Information

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IPC IPC(8): A01N25/32C07D265/36
Inventor 付颖叶非
Owner NORTHEAST AGRICULTURAL UNIVERSITY
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