Camptothecin compound and preparation method and application in pesticide thereof

The technology of a compound, camptothecin, is applied in the field of preparation of new camptothecin compounds and pesticides, which can solve the problems of short invalidation period, difficulty in preparation of preparations, poor water solubility, etc., and achieve prolonged invalidation period and difficult Effect of decomposition and improvement of water solubility

Inactive Publication Date: 2012-05-16
李红玉
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

This new type of molecule called Camptocerin was discovered by researchers at Purdue University during 1990s but its chemical formula had certain drawbacks that were solved before this discovery. These technical improvements led to an increase in their ability to fight plants diseases such as rice blast or insect biting on crops without causing damage from harmful substances released through spray drift or rainwater runoff.

Problems solved by technology

This patented technical problem addressed in this patents relates to finding ways to make certain types of molecules called camptothensine more stable for use in agriculture products like fertilizers due to their ability to break down easily over time without losing effectiveness against harmful microorganisms found inside crops.

Method used

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  • Camptothecin compound and preparation method and application in pesticide thereof
  • Camptothecin compound and preparation method and application in pesticide thereof
  • Camptothecin compound and preparation method and application in pesticide thereof

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Experimental program
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Effect test

Embodiment 1

[0020] Preparation process of camptothecin compounds

[0021] The preparation method of the present invention is to combine 5-hydroxyethyloxycamptothecin (compound 2) with N -(1'-Oxy-2',2',5',5'-tetramethylpyrrole-amide)-3'- L -Amino acids (3a-3h) were dissolved in dry dichloromethane and a catalytic amount of N,N -lutidine, stirred for 5 minutes under the protection of nitrogen, then added dicyclohexylcarbodiimide (DCC), stirred and reacted for 2 hours under the protection of nitrogen, filtered to remove the white precipitate, and evaporated the solvent under reduced pressure, the crude product Purified by column chromatography and eluted with chloroform-methanol at a volume ratio of 40:1 to obtain compounds of formula I (4a-4h).

[0022] For related reactions, see Reaction Scheme 1.

[0023]

[0024] Reaction 1

[0025] R in Formula 1 is hydrogen, methyl, methylsulfomethylene, isopropyl, butyl, isobutyl, β-indolylmethyl or benzyl.

[0026] The intermediate raw mat...

Embodiment 2

[0029] used in the present invention N -(1'-Oxy-2',2',5',5'-tetramethylpyrrole-amide)-3'- L - Amino acids ( 3a-3h ) is obtained by the following method:

[0030] Dissolve 3-carboxy-2,2,5,5-tetramethylpyrrole-nitroxyl radical (compound 5, 9.2 g, 0.05 mol) and triethylamine (5.05 g, 0.05 mol) in 100 mL of anhydrous ether , and the mixture was cooled to 0 °C with stirring. Slowly add ethyl chloroformate (5.42g, 0.05mol) dropwise. After the dropwise addition, stir the mixture at room temperature for 3h, filter, evaporate the filtrate to dryness, and recrystallize with petroleum ether to obtain bright yellow needle-like crystals 6 , yield 90%. The resulting compound 6 (10.25g, 0.04mol) was immediately added to the stirred mixed solution of sodium azide (3.88g, 0.06mol) in 75mL of acetone and water, stirred for 30min under ice bath, then extracted with n-hexane, the extract Dry with anhydrous sodium sulfate, remove the solvent under reduced pressure, and cool the residual liq...

Embodiment 3

[0038] 5-O-ethylhydroxyl-[ N -(1'-Oxy-2',2',5',5'-tetramethylpyrrole-amide)-3'-L- Glycine] camptothecin ester ( 4a )Synthesis

[0039] 3-carboxy-2,2,5,5-tetramethylpyrrole-nitroxyl (Compound 5) (9.2g, 0.05mol) and triethylamine (5.05g, 0.05mol) were dissolved in 100mL of anhydrous ether, and the mixture was cooled to 0°C under stirring. Ethyl chloroformate (5.42g, 0.05mol) was slowly added dropwise. After the dropwise addition, the mixture was stirred at room temperature for 3h, filtered, the filtrate was evaporated to dryness, and recrystallized with petroleum ether to obtain Compound 6, for Bright yellow needle-like crystals, 11.6g, 90% yield, melting point: 63-65°C.

[0040] compound 6 (10.25g, 0.04mol) was immediately added to the stirred mixed solution of sodium azide (3.88g, 0.06mol) in 75mL of acetone and water, stirred for 30min under ice bath, then extracted with n-hexane, the extract Dry with anhydrous sodium sulfate, remove the solvent under reduced pressure...

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Abstract

The invention relates to a new camptothecin compound, and a preparation method and an application in pesticides of the compound. The preparation method of the compound comprises the following steps: allowing N-(1'-oxyl-2',2',5',5'-tetramethyl pyrrole-amide)-3'-L-amino acid and 5-hydroxyethyl oxyl camptothecin to react under the action of a proper amount of catalysts and dehydrants, and performing purification and separation. Insecticidal, antibacterial and herbicidal activity testing of the compound demonstrates that when compared with camptothecin and DRF-1042, the compound has good poison activity on agricultural pests (such as brontispa longissima, spodoptera litura), and has good inhibition effect on plant germs (such as mango anthracnose and botryodiplodia theobromae) and farmland weeds (such as crabgrass, mustard, and amaranth).

Description

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Claims

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Application Information

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Owner 李红玉
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