Insect kinin analogues and application thereof in pest control

A technology of insect kinin and analogues, which is applied in the field of insect kinin analogues and their application in pest control, can solve the problems of kinin analogues with not very prominent biological activity and large molecular weight, and achieve obvious insecticidal activity , good anti-efficiency effect

Active Publication Date: 2018-07-13
CHINA AGRI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the biological activity of these kinin analogs is still not very prominent, and the molecular weight is relatively large, and there are still certain limitations in the direct application of pesticide molecules in agricultural production.

Method used

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  • Insect kinin analogues and application thereof in pest control
  • Insect kinin analogues and application thereof in pest control
  • Insect kinin analogues and application thereof in pest control

Examples

Experimental program
Comparison scheme
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preparation example Construction

[0022] The preparation of compound shown in embodiment 1, I-A-1 (Raa comes from 2-chlorophenylalanine)

[0023] The compound shown in I-A-1 is prepared by the polypeptide solid-phase synthesis method, and the specific steps are as follows:

[0024] After checking the air tightness of the peptide synthesizer, take Rink Amide-Am resin (0.3mmol) and place it in 5mL DCM for activation for 2h, then wash it with DMF for 5 times, add 5mL of 20% piperidine in DMF and react for 20min to remove the resin Add Fmoc protecting group; prepare 5mL of DMF solution containing Fmoc-Gly-OH (1.2mmol), HBTU (1.2mmol), HOBt (1.2mmol), DIEA (1.2mmol), and react with the resin for 2h at room temperature after activation for 5min Get Fmoc-Gly with Rink Amide-Amresin. Continue to remove the Fmoc group, and insert Fmoc-Trp(Boc)-OH, Fmoc-β-Ala-OH, Fmoc-L-2-Cl-Phe-OH and cinnamic acid sequentially in the same way. Finally, a mixed solution of trifluoroacetic acid: phenol: sulfide anisole: water = 90:5:2...

Embodiment 32、I-C-10

[0087] Preparation of the compound shown in Example 32, I-C-10 (Raa comes from hydroxyproline)

[0088] The compound shown in I-C-10 was prepared according to the same steps as in Example 23, except that Fmoc-Glu-OH was replaced by Fmoc-Hyp-OH. The structural identification data are shown in Table 1, and the structure is verified to be correct.

[0089] Preparation of the compound shown in Example 33, I-C-11 (Raa comes from valine)

[0090] The compound shown in I-C-11 was prepared according to the same steps as in Example 23, except that Fmoc-Glu-OH was replaced by Fmoc-Val-OH. The structural identification data are shown in Table 1, and the structure is verified to be correct.

[0091] Preparation of the compound shown in Example 34, I-C-12 (Raa comes from isoleucine)

[0092] The compound shown in I-C-12 was prepared according to the same steps as in Example 23, except that Fmoc-Glu-OH was replaced by Fmoc-Ile-OH. The structural identification data are shown in Table 1,...

Embodiment 37

[0099] Example 37, the biological activity of the compounds of the present invention on aphids

[0100] The insecticidal activity of the compounds of the present invention against aphids is determined by the leaf-dipping method to measure the biological activity of the compounds against soybean aphids (Aphis glycines). The samples were prepared into solutions with different concentration gradients with an aqueous solution containing 0.05% Triton X-100. Soybean leaves cultivated indoors that have not been exposed to any pesticides and insects are punched out with a diameter of 15mm to punch out leaves of suitable size, immersed in the diluted medicinal solution, taken out after 15s to dry, and placed in a bioassay plate. The back of the leaf faces upwards, 1% agar is added to the bottom to keep it moist, and 20±3 soybean aphids are inserted into each well. Place them in an artificial climate box at a temperature of (25±1)°C, and check the number of aphid deaths after 48 hours....

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Abstract

The invention discloses insect kinin analogues and application thereof in pest control. The structural formula of the insect kinin analogues is shown as a formula I, wherein the formula I, Raa is H oris from natural amino acid or unnatural amino acid. The insect kinin analogues are characterized in that a strategy and method of peptidomimetics are adopted; a turning point Phe2 of an active conformation VI type beta bend of an active kinin analogue is subjected to substituted modification, i.e., substitution is performed on Phe2 side chain aromatic ring; meanwhile, piperidine ring, saturated six-membered ring, hydrophobic group and hydrophilic group similar to a benzene ring structure are introduced to carry out substituted modification, and thus novel insect kinin analogues with novel structures are invented. The novel compound has obvious insecticidal activity, particularly has a good control effect on aphid and can be applied to control over agricultural pests such as the aphid. (The formula I is shown in the description).

Description

technical field [0001] The invention belongs to the technical field of pest control, and in particular relates to a class of insect kinin analogs and their application in pest control. Background technique [0002] Insect kinins are a class of active peptides ubiquitous in invertebrates and have various physiological functions. In 1984, American scientist Holman et al. first isolated 5 octapeptides with the activity of promoting hindgut contraction from Madeira cockroach brain extract, and then 3 more octapeptides were extracted. These eight peptides were named Leueokinin I-VIII because they were isolated from Madeira cockroach. People have also isolated such peptides in crickets and locusts, and then used a variety of biological and pharmacological methods to isolate and extract new peptides in different insects, such as cotton bollworm, Culex mosquito, Aedes mosquito, and American cockroach. Insect kinins, Nieto et al. also isolated 6 kinds of kinins of this family from ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07K5/023C07K1/04A01N37/46A01N47/44A01P7/04
CPCA01N37/46A01N47/44C07K5/0202
Inventor 杨新玲李欣潞张喆凌云汪梅子宋敦伦陈梦婷张怡萌
Owner CHINA AGRI UNIV
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