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A kind of abamectin derivative substituted by organophosphorus group and its preparation method and application

A technology of avermectin and organophosphorus, which is applied in the preparation of sugar derivatives, botanical equipment and methods, sugar derivatives, etc., can solve problems such as small advantages, insufficient stability, and no attention to insecticidal effects.

Active Publication Date: 2021-05-14
HEBEI VEYONG BIO CHEM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, due to insufficient stability and low activity, Abamectin B 2 As a major component of abamectin, it is largely idle, and in existing literature and patents, abamectin B 2 The synthesis and application exploration of derivatives are all rarely reported, and along with the enlargement of Abamectin production, for B 2 Exploration and application of components becomes increasingly important
[0004] Nowadays, great progress has been made in the research on abamectin derivatives. For example, Merck Company of the United States uses Wilkinson catalysis for the double bond between C22 and C23 of AVM B1, which is obtained after hydrogenation in a homogeneous system. Ivermectin; In the 4 " position of AVM B1, the introduction of methylamino can obtain 4 "-methylamino-4 "-deoxyabamectin benzoate; utilize mutation biosynthesis at the C25 of Abamectin The cyclohexane group is connected to obtain dauramectin; abamectin B is disclosed in Chinese patent application 201310063563.0 2a / B 2b Amino derivatives and abamectin B substituted with alkylated or acylated amino groups at the 4" position 2a / 2b Derivatives, which expand the abamectin B 2 scope of utilization, it does not pay attention to the insecticidal effect of abamectin; a kind of virus insecticidal suspension containing abamectin is disclosed in Chinese patent application 201410721599.8, wherein said abamectin and virus are pressed The compounding ratio of its invention speeds up the insecticidal speed to a certain extent, and the insecticidal effect is even faster. It only targets a variety of conventional agricultural and forestry pests diamondback moth, pine caterpillar, and cabbage caterpillar, and does not pay attention to the target Insecticidal effect of rice stem borer, citrus spider mite, rice planthopper and other pests
[0005] At the same time, with the popularity and promotion of abamectin and its downstream products in recent years, its drug resistance has become more and more obvious. In addition, abamectin itself is very serious in thermal degradation and photodegradation, and its duration is short. Compared with chemical pesticides, its advantages are getting smaller and smaller

Method used

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  • A kind of abamectin derivative substituted by organophosphorus group and its preparation method and application
  • A kind of abamectin derivative substituted by organophosphorus group and its preparation method and application
  • A kind of abamectin derivative substituted by organophosphorus group and its preparation method and application

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] Embodiment 1 compound 1,4 "-diethyl phosphate methylamino abamectin B 1a / B 1b preparation of

[0035] 5g 5-allyloxycarbonyl-4"-carbonyl abamectin B 1a / B 1b (Content>90%) dissolved in 20g sec-butyl acetate, add 4.9g heptamethyldisilazane, 2.8g diethyl phosphite and 1.1g zinc trifluoroacetate in sequence, keep stirring at 50°C , reacted for 2h, then cooled to -10°C, added 8g methanol, 0.55g sodium borohydride and 0.003g triphenylphosphine palladium chloride, reacted for 0.5h, then added 7.6% phosphoric acid solution to adjust the pH value to 2, and then used 10 % sodium hydroxide solution to adjust the pH value to 7, let stand and separate layers, dry the organic layer with anhydrous sodium sulfate, remove the solvent under reduced pressure, and purify by column chromatography to obtain a light yellow solid, namely compound 1,4 "-diethyl phosphate abamectin B 1a / B 1b , its content >90%.

[0036] Its hydrogen spectrum is: 1 H NMR (CDCl 3 )δppm: 5.95 (m, 1H), 5....

Embodiment 2

[0039] Embodiment 2 compound 1,4 "-diethyl phosphate methylamino abamectin B 2a / B 2b preparation of

[0040] 5g 5-allyloxycarbonyl-4"-carbonyl abamectin B 2a / B 2b (Content>90%) was dissolved in 20g of sec-butyl acetate, 5g of heptamethyldisilazane, 3g of diethyl phosphite and 1.2g of zinc trifluoroacetate were added successively, kept at 50°C while stirring, and reacted 2h, cool down to -10°C, then add 8g methanol, 0.6g sodium borohydride and 0.003g triphenylphosphine palladium chloride, react for 0.5h; add 7.6% phosphoric acid solution to adjust the pH value to 2, and then use 10% hydroxide Adjust the pH value to 7 with sodium solution, let stand, separate layers, dry the organic layer with anhydrous sodium sulfate, remove the solvent under reduced pressure, and purify by column chromatography to obtain a light yellow solid, namely compound 1,4"-diethyl phosphate Ethylaminocarbamectin B 2a / B 2b , its content >90%.

[0041] Its hydrogen spectrum is: 1 H NMR (CDCl 3...

Embodiment 3

[0044] Embodiment 3 compound 2,4 "-diethyl phosphate group hydroxyl abamectin B 2a / B 2b preparation of

[0045] 5g 5-allyloxycarbonyl-4"-carbonyl abamectin B 2a / B 2b (content >90%) was dissolved in 20g of dichloromethane, 0.7g of diethyl phosphite and 0.5g of triethylamine were added successively, kept at 50°C for 2h, cooled to -10°C, and then added with 8g of methanol, 0.6 g sodium borohydride, 0.003 g triphenylphosphine palladium chloride reacted for 0.5 h, then added 7.6% phosphoric acid solution to adjust the pH value to 2, and then adjusted the pH value to 7 with 10% sodium hydroxide solution, let stand, and layered, Dry with anhydrous sodium sulfate, remove the solvent under reduced pressure, and purify by column chromatography to obtain a light yellow solid, namely compound 2, 4"-diethyl phosphate hydroxyabamectin B 2a / B 2b , its content >90%.

[0046] Its hydrogen spectrum is: 1 H NMR (CDCl 3)δppm: 5.84-5.95 (m, 3H), 5.55 (dd, J = 0.8, 2.6, lH), 5.47 (d, J =...

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Abstract

The invention discloses an organophosphorus group substituted abamectin derivative and its preparation method and application. Its general structural formula is shown in (I), and the definition of each substituent in the formula can be found in the description. The present invention uses abamectin as a parent to synthesize a series of abamectin derivatives substituted by organophosphorus groups, thereby expanding the utilization range of abamectin, and simultaneously the abamectin derivatives can be used for various plant pests It is especially suitable for the prevention and control of Lepidoptera pests, mite pests, aphids, and it has a strong insecticidal effect on target rice stem borers, citrus red spiders, rice planthoppers and other pests; the organophosphorus-based Group-substituted abamectin derivatives are significantly better than abamectin B against target pests such as rice stem borer, citrus red spider, and rice planthopper 1a / B 1b , also significantly better than abamectin B 2a / B 2b , Increase the insecticidal spectrum and improve the activity.

Description

technical field [0001] The invention relates to the technical field of agricultural chemicals and their preparation, in particular to an abamectin derivative substituted by an organophosphorus group, a preparation method and application thereof. Background technique [0002] Avermectin (AVM for short) is a low-toxicity, high-efficiency, high-selection, green, environmental-friendly and biological source insecticide, which completely solves the high toxicity, resistance and environmental impact of traditional pesticides. problem of impact. [0003] Currently commercially available abamectin pesticides are based on B 1a as the main insecticidal ingredient (Avermectin B 1a +B 1b , where B 1a Not less than 90%, B 1b not more than 5%) to B 1a content to calibrate. Abamectin B 1 Great progress has been made in the research on derivatives of abamectin. Nearly a thousand kinds of avermectin derivatives have been synthesized. Emamectin, emamectin, dauramectin and mibamycin, ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07H17/08C07H1/00A01N57/24A01P7/04A01P7/02
CPCA01N57/24C07H1/00C07H17/08Y02P20/55
Inventor 王博田学芳范朝辉闫艳艳张博贾成国
Owner HEBEI VEYONG BIO CHEM