Azabicyalo derivative as well as preparation and application thereof

An azabicycle, derivative technology, applied in the fields of botanical equipment and methods, applications, chemicals for biological control, etc., can solve problems such as environmental damage

Active Publication Date: 2016-02-03
EAST CHINA UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, these commercial nematicides are highly toxic compounds that cause serious damage to the environment

Method used

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  • Azabicyalo derivative as well as preparation and application thereof
  • Azabicyalo derivative as well as preparation and application thereof
  • Azabicyalo derivative as well as preparation and application thereof

Examples

Experimental program
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Effect test

preparation example Construction

[0076] The preparation methods of the compounds of the present invention are described in more detail below, but these specific methods do not constitute any limitation to the present invention. The compound of the present invention can also be conveniently prepared by optionally combining various synthetic methods described in the specification or known in the art. Such a combination can be easily performed by those skilled in the art to which the present invention belongs.

[0077]Usually, in the preparation process, each reaction is usually carried out in an inert solvent at room temperature to reflux temperature (such as 20°C-160°C, preferably 50°C-120°C). The reaction time is usually 0.1 hour to 60 hours, preferably 0.5 to 1 hour.

[0078] For the convenience of description, hereinafter, the compound represented by formula 1 is referred to as compound 1 for short, and the rest are deduced by analogy.

[0079] In a preferred example, compound (III) is taken as an example ...

preparation example 1

[0120] Intermediate Preparation Example 1: Synthesis of Tropinone Oxime

[0121]

[0122] 1.39g (10mmol) of tropinone, 1.05g (15mmol) of hydroxylamine hydrochloride and 1.60g (20mmol) of anhydrous acetic acid manganese were dissolved in 30ml of absolute ethanol solution, and the system was stirred and refluxed for 3 to 4 hours. Pinone reacts completely. Add 10% NaOH solution to adjust the pH value to 10-11. The solvent ethanol was distilled off to obtain the crude product, which was washed with water, extracted with ethyl acetate and anhydrous MgSO 4 After drying, the solvent was removed to obtain a pure product with a yield of 90%. 1 HNMR (400MHz,) δ3.28(d, J=11.7Hz, 2H), 2.98(d, J=15.5Hz, 1H), 2.59(d, J=14.7Hz, 1H), 2.36(s, 3H), 2.22(dd, J=15.4, 2.9Hz, 1H), 2.12(d, J=14.7Hz, 1H), 1.99(d, J=3.8Hz, 2H), 1.58(t, J=9.1Hz, 1), 1.47(t,J=9.0Hz,1H). 13 CNMR (101MHz, CDCl 3 )δ155.6,60.7,59.9,39.0,37.0,30.9,27.2,26.3.MS(GC-MS):m / z154(M + ), 137, 96, 82.

preparation example 2

[0124] 2.12-(allyloxy)isoindoline-1,3-dione

[0125] Dissolve 8.1g (50mmol) N-hydroxyphthalimide and 6.9g (50mmol) anhydrous potassium carbonate in 100mL DMF, slowly add 6g (50mmol) allyl bromide dropwise, and stir at room temperature. According to TLC tracking, the reaction ended after 24 hours. The reaction solution was poured into ice water, and a white solid was precipitated, filtered, washed with deionized water, and dried to obtain 29.1 g of a white solid intermediate with a yield of 90%. Melting point: 55-57°C; 1 HNMR (400MHz, CDCl 3 )δ7.84(s,2H),7.78(s,2H),6.21–6.08(m,1H),5.44–5.32(m,2H),4.75–4.69(m,2H). 13 CNMR (101MHz, CDCl 3 )δ163.7, 134.4, 131.2, 128.8, 123.5, 122.5, 78.8.

[0126] 2.2O-allyl hydroxylamine hydrochloride

[0127] Add 9.1g (45mmol) of 2-(allyloxy)isoindoline-1,3-dione and 2.81g (45mmol) of 80% hydrazine hydrate into 100mL of absolute ethanol, heat and reflux for 2 hours, and then Cool down to room temperature and continue to stir the reaction f...

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PUM

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Abstract

The invention relates to an azabicyalo derivative as well as preparation and application thereof, and particularly discloses a compound with a structure shown in to the formula (A) or salt thereof acceptable in agricultural pharmacology. The compound in the formula (A) is described in the description in detail, and has an excellent killing effect on nematode.

Description

technical field [0001] The invention belongs to the field of pesticides. Specifically, the present invention relates to an azabicyclic derivative and its preparation and application, in particular, its application as a nematicide. Background technique [0002] The phylum Nematoda (scientific name: Nematoda) is one of the largest phylums in the animal kingdom. It is a pseudocoelomate, with more than 28,000 recorded species and a large number of species that have not yet been named. Many nematodes have successfully evolved into animal and plant parasites, which have caused huge economic losses in agriculture and animal husbandry. It is conservatively estimated that plant parasitic nematodes cause economic losses of US$ 100 billion in agriculture and forestry worldwide every year. At present, only a few chemical agents can effectively control the harm of nematodes. Examples: methyl bromide, 1,3-dichloropropene, organophosphorus and carbamate nematicides. However, these comme...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D451/02C07D221/22C07D401/12C07D405/12A01N43/90A01N47/16A01N47/24A01N43/42A01P5/00
Inventor 宋恭华陆青徐俊孙璐王佳毅徐蓓玲崔佳露周晓英朱佶鹏郑一汀符小根
Owner EAST CHINA UNIV OF SCI & TECH
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