Oxime ester thiophosphoramide compounds as well as preparation method and application thereof

A technology of oxime ester thiophosphoramide and compound, which is applied in the field of oxime ester thiophosphoramide compound and its preparation, can solve problems such as non-industrialized varieties, and achieve the effects of good commercial development value, easy handling and few steps

Active Publication Date: 2021-12-14
QINGDAO AGRI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] Existing organophosphorus pesticides can be divided into phosphate esters, phosphorothioate esters, phosphoramides and phosphorothioate amides, pyrophosphate esters and phosphine Esters and thiophosphonates, and oxime esters and thiophosphoramides are still blank, and there are no related industrialized varieties so far.

Method used

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  • Oxime ester thiophosphoramide compounds as well as preparation method and application thereof
  • Oxime ester thiophosphoramide compounds as well as preparation method and application thereof
  • Oxime ester thiophosphoramide compounds as well as preparation method and application thereof

Examples

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preparation example Construction

[0055] Based on the same inventive concept, the present invention also provides a preparation method of a group of oxime ester thiophosphoramide compounds, which specifically includes the following steps:

[0056]

[0057] Among them, R 1 , R 2 , R 3 range with the above R 1 , R 2 , R 3 The scope is the same and will not be repeated here;

[0058] (1) Add a certain amount of a to the three-necked bottle, heat and dissolve with methanol, and then add the calculated amount of Na 2 CO 3 , drip hydroxylamine hydrochloride aqueous solution under stirring, a large amount of solids are arranged, and stirring reflux continues to react, after reaction finishes, suction filtration, washing, obtain light yellow solid b; In step (1) of the present invention, a, Na 2 CO 3 The molar ratio to hydroxylamine hydrochloride is preferably 1:1:1.2.

[0059] (2) Add ethanol and the calculated amount of metal Na to a dry three-neck flask equipped with a stirrer, a thermometer, a drying t...

Embodiment 1

[0069] The preparation of embodiment 1 compound A

[0070] (1) Add 0.02mol piperonal to a 100mL three-necked bottle, heat to dissolve with 15mL methanol, add 0.02molNa 2 CO 3 . Add a solution of 0.024mol hydroxylamine hydrochloride and 3mL water dropwise under stirring, a large amount of solids are formed, stir and reflux to continue the reaction, use TLC (the volume ratio of petroleum ether to ethyl acetate is 5:1) detection, until the raw material point disappears , suction filtration, and washing with water to obtain 3.15 g of light yellow solid piperoxime, with a yield of 95.5%.

[0071] (2) Add 100mL of ethanol to a dry 250mL three-necked flask equipped with a stirring bar, a thermometer, a drying tube, and a condenser tube, add 0.1mol of metal Na, and heat up to 50°C for reaction until all Na disappears, and then add (1) to prepare 0.05 mol of piperoxime, under stirring, the temperature was raised to reflux, and a light yellow solid gradually precipitated. After 10 ho...

Embodiment 2

[0073] The preparation of embodiment 2 compound B

[0074] The preparation process is the same as Example 1, and the differences are as follows:

[0075] (1) The reactant piperonal was replaced by 3,4-methylenedioxyphenyl cyclopropyl ketone, and the product yield in step (1) was 94.1%.

[0076] (2) The reactant piperoxime was replaced by 3,4-methylenedioxyphenylcyclopropylmethoxime, and the yield of the product in step (2) was 93.2%.

[0077] (3) The reactant piperoxime sodium salt was replaced with 3,4-methylenedioxyphenylcyclopropylmethoxime sodium salt, and the yield of compound B was 68.9%.

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Abstract

The invention discloses a group of oxime ester thiophosphamide compounds with a structure as shown in the specification, wherein R1, R2 and R3 are independently selected from alkyl groups. The invention further discloses a preparation method of the oxime ester thiophosphoramide compounds with the structure shown in the formula (I) and application of the oxime ester thiophosphoramide compounds in preparation of pesticides for preventing and controlling agricultural pests. The oxime ester thiophosphamide compounds with the structure provided by the invention generate less 'three wastes' in the preparation process, are easy to treat, and have the advantages of greenness and good environmental compatibility when being produced as pesticides. The compounds can be used for preventing and treating agricultural and forestry pests, have the advantages of broad spectrum, high efficiency, low toxicity and the like, can also be applied to pests with drug resistance, have a good effect on preventing and treating lepidoptera pests such as cotton bollworms, ostrinia nubilalis, plutella xylostella and beet armyworms, are far superior to organic phosphorus pesticides in the prior art, have a good application prospect, and are low in cost and good in economic benefits.

Description

technical field [0001] The invention belongs to the field of environment-friendly pesticides, and in particular relates to a group of oxime ester thiophosphoramide compounds and a preparation method and application thereof. Background technique [0002] During World War II, German Schrader et al. conducted research on organophosphorus compounds and discovered the biological activity of organophosphorus compounds such as octaphos, tepp and parathion, and the end of the war was announced to the world. Due to the outstanding insecticidal activity of these compounds, they have attracted extensive attention from all over the world. Since then, organophosphorus insecticides have continued to develop and new varieties have emerged, gradually developing into one of the main types of worldwide insecticides. With the development of less toxic varieties such as phoxim, malathion, trichlorfon and other high-efficiency organophosphorus pesticides, organophosphorus pesticides once accoun...

Claims

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Application Information

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Patent Type & AuthorityApplications(China)
IPC IPC(8): C07F9/655A01N57/32A01P7/04
CPCC07F9/65517A01N57/32
Inventor孙家隆张维杰宋敬诚李娜侯婷翟晓璐刘柯
OwnerQINGDAO AGRI UNIV