Piperazine amide derivative and preparation method thereof, root parasitic weed seed germination accelerator and method for preventing and controlling root parasitic weeds

A technology of piperazinamide and derivatives, applied in the field of pesticide chemistry, can solve problems such as ineffective prevention and control of root parasitic weeds, and achieve the effects of being favorable for commercialization, low in preparation cost, and promoting germination

Active Publication Date: 2020-08-04
NANKAI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, there is no effective herbicide to control root parasitic weeds, and the annual economic loss caused by root parasitic weeds is as high as 10 billion US dollars

Method used

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  • Piperazine amide derivative and preparation method thereof, root parasitic weed seed germination accelerator and method for preventing and controlling root parasitic weeds
  • Piperazine amide derivative and preparation method thereof, root parasitic weed seed germination accelerator and method for preventing and controlling root parasitic weeds
  • Piperazine amide derivative and preparation method thereof, root parasitic weed seed germination accelerator and method for preventing and controlling root parasitic weeds

Examples

Experimental program
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Effect test

preparation example Construction

[0055] The second aspect of the present invention provides the preparation method of the piperazine amide derivative of the present invention, the method comprises the following steps:

[0056] (1) In the first solvent, carry out condensation reaction with raw material A shown in formula (1-1), raw material B shown in formula (1-2), coupling agent and condensing agent, obtain formula (1-3 ) intermediate C shown in );

[0057] (2) In the second solvent, the intermediate C is subjected to a deprotection reaction with a deprotecting agent to obtain an intermediate D represented by formula (1-4);

[0058] (3) In the third solvent, the acid chlorination reaction of the intermediate D, the acyl chloride agent represented by the formula (1-5) and the first base occurs to obtain the intermediate E represented by the formula (1-6) ;

[0059] (4) In the fourth solvent, the intermediate E, the raw material F represented by the formula (1-7) and the second base undergo an esterification...

Embodiment 1

[0124] Embodiment 1---the synthesis of compound 52

[0125] (1) the raw material A (R) shown in the formula (1-1) of 15mmol 1 ~R 7 , X is selected as shown in compound 52 of Table 1, R 11 = H), 15 mmol of raw material B (tert-butoxycarbonyl piperazine) shown in formula (1-2), 19.5 mmol of coupling agent (2-(7-benzotriazole oxide)-N,N, N', N'-tetramethyluronium hexafluorophosphate) and 150 mL of the first solvent (dichloromethane) were added to the reaction flask, and 43.5 mmol of condensing agent (N, N '-diisopropylethylamine, DIPEA) and continued to react at room temperature for 8 hours. After the reaction was completed, 100 mL of water was added to the system and vigorously stirred for 15 min. Separate the organic layer, wash the water layer with 50mL of the first solvent, combine the organic layers, wash the organic layer with water and saturated brine successively, dry with anhydrous sodium sulfate, and remove the organic solvent under reduced pressure to obtain the fo...

Embodiment 2

[0136] Embodiment 2 --- the synthesis of compound 46

[0137] With reference to the method of Example 1, the difference is that the raw materials used are different to prepare the compound 46 in Table 1, in the specific raw materials R 1 ~R 9 , X and Z are selected as shown in compound 46 in Table 1, R 11 =H.

[0138] The yield is 90%.

[0139] The proton spectrum data of gained compound is: 1 H NMR (400MHz, CDCl 3 )δ6.94–6.74(m,5H),4.70(s,2H),3.85–3.32(m,8H),2.23(s,3H),1.99(s,3H).

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Abstract

The invention relates to the field of pesticide chemistry, in particular to a piperazine amide derivative and a preparation method thereof, a root parasitic weed seed germination accelerator and a method for preventing and treating root parasitic weeds. In the derivative (See the specification for the formula), R<1>, R<2>, R<3>, R<4> and R<5> are respectively and independently selected from hydrogen, halogen, nitro, cyano, chain alkyl, alkyl containing a cyclic structure, alkoxy, halogenated alkoxy, alkylthio, ester group, alkyl sulfonyl and the like or are connected together to form a cyclicstructure, X is selected from O, S, SO, SO2 or CR<10>R<11>, R<6>, R<7>, R<10>, R<11> are each independently selected from hydrogen, halogen and C1-C4 alkyl or are connected together to form a three-membered ring, a four-membered ring or a five-membered ring, Z is selected from O or S, and R<8> and R<9> are each independently hydrogen or an alkyl group of C1 to C4. The piperazine amide derivative disclosed by the invention can be used as a root parasitic weed seed germination accelerator.

Description

technical field [0001] The invention relates to the field of pesticide chemistry, in particular to a piperazine amide derivative and a preparation method thereof, a root parasitic weed seed germination accelerator and a method for preventing and controlling root parasitic weeds. Background technique [0002] Striga and letang are root parasitic weeds, which parasitize the roots of crops, such as corn, sorghum, sunflower, melons, tomatoes and cereals, absorb water and nutrients from the host roots, causing severe crop yield reduction, or even failure . Striga and Liedang are distributed all over the world, among which Striga is mainly distributed in subtropical and tropical regions, and Liedang is mainly distributed in subpolar and temperate regions. In the Xinjiang region of China alone, more than 100 million mu of crops are harmed by root parasitic weeds every year. At present, there is no effective herbicide for controlling root parasitic weeds, and the annual economic l...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D307/60A01N47/16A01P13/00A01P21/00
CPCC07D307/60A01N47/16
Inventor 席真王大伟庞智黎
Owner NANKAI UNIV
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