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Pyrrolidone sulfur derivatives and their preparation method and application

A technology of sulfur derivatives and pyrrolinone, which is applied in the field of sulfur derivatives of pyrrolinones and their preparation and application, and can solve the problems of easy loss of activity, spatial structure transformation, high cost and price of L-isoleucine, etc.

Active Publication Date: 2015-12-09
NANJING AGRICULTURAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] The artificially synthesized 2-acetyl-4-hydroxy-5-sec-butylpyrrolin-2-one is synthesized from L-isoleucine, but the cost of L-isoleucine is very high, and the previous Synthetic side chains are hydrocarbon chains
The artificially synthesized 2-acetyl-4-hydroxy-5-sec-butylpyrrolin-2-one is unstable at room temperature and is prone to change in spatial structure, making it difficult to prepare dosage forms and easily lose activity

Method used

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  • Pyrrolidone sulfur derivatives and their preparation method and application
  • Pyrrolidone sulfur derivatives and their preparation method and application
  • Pyrrolidone sulfur derivatives and their preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039] 3-acetyl-4-hydroxyl-5-mercaptomethyl-pyrroline-2-one (compound 1), its structural formula is:

[0040]

[0041] Its synthetic steps are:

[0042] Step 1. Preparation of L-cysteine ​​methyl ester hydrochloride: Slowly add 0.12mol of thionyl chloride to 50mL of anhydrous methanol dropwise at -11°C. After stirring for 1 hour, add 0.1mol of L-cysteine After stirring at room temperature for 3 hours, stirring at 65°C for 4 hours, rotary evaporation, dissolving the reaction product in a mixed solvent of ethyl acetate and petroleum ether (volume ratio 1:1), crystallization was obtained at 0°C,

[0043] Step 2. Preparation of N-acetoacetylcysteine ​​methyl ester: take 0.1 mol of the crystals obtained in step 1, dissolve in 50 mL of anhydrous methanol, add 0.1 mol of freshly prepared sodium methoxide to neutralize and remove hydrochloric acid, and then place in an ice-water bath at -10 °C 0.15mol diketene was added dropwise, stirred at room temperature for 16h, and 1M HCl and...

Embodiment 2

[0047] With reference to the preparation method of Compound 1 in Example 1, by adjusting the sulfur-containing amino acid as the starting material, the corresponding sulfur derivatives of pyrrolidones were synthesized, the reaction conditions and the ratio of raw materials used and the reaction conditions and raw materials used for preparing Compound 1 than the same.

[0048] Compound 2: Synthesis of 3-acetyl-4-hydroxy-5-(methyl-mercaptomethyl)-pyrroline-2 from 2-amino-3-(methyl-mercaptomethyl)propionic acid as starting material -ketone.

[0049] Compound 2: m.p.197.1-197.6°C. EI-MSm / z(%): 202[M+H] + , 155, 141(100), 98, 84, 48. 1 H-NMR (CDCl 3 , 500MHz), δ: 2.03 (t, J=7.0Hz, 3H, SCH 3 ), 2.51~2.54 (m, 2H, SCH 2 ), 2.34(s, 3H, COCH 3 ), 3.75 (d, J = 6.0 Hz, 1H, NCH), 7.63 (s, 1H, NH), 12.65 (s, 1H, OH).

[0050]

[0051] Compound 3: Synthesis of 3-acetyl-4-hydroxy-5-(ethyl-mercaptomethyl)-pyrroline-2 from 2-amino-3-(ethyl-mercaptomethyl)propionic acid as starting ma...

Embodiment 3

[0160] Take the above 38 sulfur derivatives of pyrrolinones (compound 1-6, compound 9-40), dissolve them with a small amount of methanol, and then prepare solutions with concentrations of 1 mg / L and 2 mg / L with distilled water, and set the same concentration Methanol solvent control and water control, Eupatorium adenophorum leaf acupuncture method for pathogenicity detection, each treatment repeated more than 6 times, 25 ° C, kept in natural light for 24 hours, and then measured the diameter of the lesion with a micrometer .

[0161] The results are shown in Table 1, indicating that sulfur derivatives of pyrrolinones have higher pathogenicity to Eupatorium adenophorum, and under the same concentration conditions, the longer the branch chain at the 5-position, the higher the pathogenicity.

[0162] Table 138 Pathogenicity data of sulfur derivatives of pyrrolinones to Eupatorium adenophorum

[0163]

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Abstract

The invention belongs to the field of pesticide and plant protection and discloses pyrrolidone sulfur derivatives or their physiologically soluble salts. The pyrrolidone sulfur derivatives have a structural formula (I), wherein R=-(CH<2>)nSCmH<2>m<+1>, n is an integer of 1-7, m is an integer of 0-5, the case of n=2 and m=1 is excluded and the case of n=2 and m=2 is excluded. The invention also discloses a preparation method of the pyrrolidone sulfur derivatives or a use of the pyrrolidone sulfur derivatives in prevention and control of weeds. Compared with the original compound, the pyrrolidone sulfur derivatives or their physiologically soluble salts have higher weeding activity and a lower synthesis cost and can be stored easily. After contacting with the pyrrolidone sulfur derivative liquid, weeds produce cell death and brown disease spots at the contacting positions. The pyrrolidone sulfur derivative liquid can kill weeds usually in 3-5 days, has weeding broad spectrum activity, has small environmental pollution and less residue, has little activity after entering into solid in use, can be passivated fast and has very high environment safety.

Description

technical field [0001] The invention belongs to the technical field of application of chemistry and biochemistry to agricultural pesticides, plant protection, and control of crop weeds, and relates to a sulfur derivative of pyrrolidones and its preparation method and application, in particular to Alternaria with herbicidal activity A structurally modified product of the bacterial metabolite Alternaria tenoic acid (chemical name: 3-acetyl-4-hydroxyl-5-sec-butylpyrrolin-2-one) and its preparation method and application. technical background [0002] Tenuazonic acid (TeA) is a toxin isolated from the metabolites of the pathogenic bacteria Alternaria tenuazonica of the vicious weed Eupatorium adenophorum, and its chemical name is 2-acetyl-4- Hydroxy-5-sec-butylpyrrolin-2-one, which is the main pathogenic factor of Alternaria tenones that can cause brown spot of various plants. TeA-containing metabolites of Alternaria tenones are active against most of the weeds in farmland and ...

Claims

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Application Information

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IPC IPC(8): C07D207/38A01N43/36A01P13/00
CPCA01N43/36C07D207/38
Inventor 强胜姚沁
Owner NANJING AGRICULTURAL UNIVERSITY
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