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Hemigossypol derivative, vergosin derivative, preparation of hemigossypol derivative and vergosin derivative and application to pesticides

A technology of semigossypol and derivatives, which is applied in the field of pesticides and achieves the effects of good water solubility, good environmental compatibility and significant anti-plant virus activity

Active Publication Date: 2016-08-24
NANKAI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

But so far, no chemical pesticide has been able to completely cure plants once they are infected with TMV

Method used

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  • Hemigossypol derivative, vergosin derivative, preparation of hemigossypol derivative and vergosin derivative and application to pesticides
  • Hemigossypol derivative, vergosin derivative, preparation of hemigossypol derivative and vergosin derivative and application to pesticides
  • Hemigossypol derivative, vergosin derivative, preparation of hemigossypol derivative and vergosin derivative and application to pesticides

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0048] Embodiment 1: the synthesis of hemigossypol derivatives (I-1~I-4 and I-9~I-11)

[0049]

[0050]

[0051] Synthesis of 2-Hydroxy-6-isopropyl-3-methylbenzaldehyde (1)

[0052] Add 30.00g (200mmol) of carvacrol and 200mL of toluene into a 500mL four-necked bottle, respectively insert a thermometer, an air inlet pipe and a condenser tube on the four-necked bottle, and add 5.2g (20mmol) tin tetrachloride successively with a dropper under the protection of argon. ), triethylamine 8.08g (80mmol), after stirring at room temperature for 20min, add 13.19g (439mmol) of paraformaldehyde, heat and stabilize at 100°C and react for 8h, cool down, add dilute hydrochloric acid to adjust the pH value to 2, then add ethyl acetate Ester separation, the aqueous phase was extracted once with ethyl acetate, the organic phases were combined, extracted once with saturated sodium chloride solution, dried over anhydrous magnesium sulfate, filtered with suction, and precipitated to obtain a...

Embodiment 2

[0072] Embodiment 2: Semigossypol acid and related derivatives (I-5~I-8)

[0073]

[0074] Add 2.00g (6.61mmol) of compound I-2, 100mL of tert-butanol and 100mL of tetrahydrofuran into a 500mL round-bottomed flask. Sodium chlorite 1.50g (content > 80%, 13.27mmol) and sodium dihydrogen phosphate dihydrate 4.13g (26.46mmol) 40mL aqueous solution, slowly raised to room temperature, reacted for 10h, added saturated ammonium chloride aqueous solution 100mL, divided Liquid and aqueous phases were extracted twice with ethyl acetate, the organic phases were combined, extracted with saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, suction filtered, precipitated, and recrystallized from petroleum ether and ethyl acetate to obtain compound I-5. White solid 1.68g (5.28mmol), yield: 80.0%; melting point: 190-191°C; 1 H NMR (400MHz, CDCl 3 )δ7.54(s, 1H), 6.69(s, 1H), 4.02-3.91(m, 10H), 2.50(s, 3H), 1.50(d, J=7.1Hz, 6H); 13 C NMR (100MHz, CDCl 3 )δ175.48, 154...

Embodiment 3

[0078] Example 3: Synthesis of 3,8-dimethyl-5-isopropyl-6-methoxy-1,7-naphthalenediol (I-12):

[0079]

[0080] Add 3.00g (6.87mmol) of compound I-9, 100mL tetrahydrofuran, and 0.52g (13.75mmol) of lithium aluminum hydride into a 250mL round-bottomed flask. After stirring at room temperature for 1 hour, under an ice-water bath, slowly add dilute hydrochloric acid with a dropper to No more flocs, separate the liquids, extract the aqueous phase twice with ethyl acetate, combine the organic phases, extract with saturated saline solution, dry over anhydrous magnesium sulfate, filter with suction, and desolventize to obtain the crude product. Add 120mL of methanol, 0.3mL of concentrated hydrochloric acid, 0.30g of 10% Pd / CO, pass through hydrogen to react at room temperature for 12h, filter with suction, spin the mother liquor to dryness, column chromatography (PE:EA=50:1) to obtain compound I- 12. 1.36g (5.22mmol) of light gray solid; yield: 76.0%; melting point: 147-149°C; 1 ...

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PUM

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Abstract

The invention relates to a hemigossypol derivative, a vergosin derivative, preparation of the hemigossypol derivative and the vergosin derivative and application to preventing plant viruses, killing bacteria and killing insects. Meaning of groups in the formula is shown in the description. The hemigossypol derivative and the vergosin derivative have excellent plant virus resistance, sterilization activity and insecticidal activity. Please see the molecular formula in the description.

Description

technical field [0001] The invention relates to semi-gossypol and vergosin derivatives and their preparation and application in pesticides, belonging to the technical field of pesticides. Background technique [0002] Gossypol (Scheme1) mainly exists in cottonseed, accounting for 0.4%-1.7% of the total weight of cottonseed. Gossypol has a very wide range of biological activities: almost all cancer cells have inhibitory activity; can inhibit a variety of viruses, such as HIV, avian influenza, etc., which are now difficult to treat; have anti-parasitic activity (malaria, trypanosomiasis, etc.) ; It has bactericidal and insecticidal activity, and the content of gossypol compounds in the cotton plant and the ratio of different substances will be affected by external bacteria and insects; it also has antioxidant activity, and it has also shown its application in rubber and chemical fields etc. (Xu Zhihong, China Oils, 2008, 33, 6-10). Therefore, the research on gossypol has bec...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C47/57C07C47/575C07C45/64C07C45/29C07C43/23C07C41/26C07C41/16C07C65/24C07C51/16C07C69/94C07C67/11C07C67/31C07C67/317C07D307/92C07D307/94A01P1/00A01P3/00A01P7/04A01P7/02
Inventor 汪清民李玲刘玉秀王兹稳李永强
Owner NANKAI UNIV
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