宽胫夜蛾性信息素类似物的合成及其生物活性

doi:10.3864/j.issn.0578-1752.2022.09.008

Abstract

Abstract:

【Background】In recent years, with the significant increase in the area planted with the newly introduced crop quinoa, Protoschinia scutosa, which prefers quinoa, has gradually increased and become a major pest of quinoa, posing a potential threat to the production of agriculture in China.【Objective】The objective of this study is to synthesize two different types of analogues modified with the polar group of the sex pheromone (Z)-hexadec-11-en-1-yl acetate (Z11-16:Ac), as the parent structure, and determine the biological activity, providing a theoretical basis for using sex pheromones and analogues for the green control of P. scutosa.【Method】The sex pheromone precursor (Z)-hexadec-11-en-1-ol (Z11-16:OH) was used as the raw material, and triethylamine was used as the acid-binding agent (4-dimethylaminopyridine was added as the catalyst for the reaction with the anhydride), and the esterification reactions with 2-bromopropionyl chloride, 2-chloroacetyl chloride, difluoroacetic anhydride, trifluoroacetic anhydride, methacryloyl chloride, and 2-butenoyl chloride were carried out respectively, the halogen atom modified analogues (K1-K4) and carbon chain end double bond modified analogues (K5-K6) were synthesized, separated and purified by column chromatography. Different concentrations (0.001, 0.01, 0.1, 1, 10, 100 μg·μL^-1) of sex pheromone analogues (K1-K6) were prepared by gradient dilution. The EAG response values of analogues K1-K6 were measured by direct stimulation on the male tentacles of P. scutosa using different concentrations of analogues. Sex pheromone analogue trap lures were prepared by adding different doses of analogues to the sex pheromone. The field trapping trials were conducted in the summer of 2021 in Yanqing, Beijing, and the analogue activity was analyzed by counting the male moth in the traps.【Result】As the stimulation concentration increased from 0.001 to 100 μg·μL^-1, the electrophysiological response values of male tentacles to analogues K1 to K5 showed a gradual increase trend. Male tentacles responded most strongly to the compound (Z)-hexadec-11-en-1-yl 2-bromopropanoate (K1), with a response value of 1.34 mV at 100 μg·μL^-1. The EAG activities of analogues K5 and K6 were relatively poor, with EAG response values of 0.67 and 0.57 mV at 100 μg·μL^-1, respectively. All the six analogues synthesized showed good biological activity in field trapping experiments. K5 had the highest average trapped number of 35.00 heads at an additive level of 100 μg, which was significantly higher than the sex pheromone control. The average number of trapped adults of analogue K1 was 32.33 heads at an additive level of 10 μg during the whole period (15 d) of field trapping tests, which was significantly higher than the sex pheromone control.【Conclusion】The analogues K1 and K5 showed potentiation activity and can be used as potentiators of sex pheromones as verified by EAG and field trials. The addition of different doses of analogues K2, K3, K4 and K6 exhibited comparable activity to sex pheromones. This study provides a scientific and theoretical basis for the green control of P. scutosa.

Key words: Protoschinia scutosa, sex pheromone analogue, chemical synthesis, bioactivity, chemical control of insect behavior

LI Hui,YIN ShiCai,GUO ZongXiang,MA HaoYun,REN ZiQi,SHE DongMei,MEI XiangDong,NING Jun. Synthesis and Bioactivity of Sex Pheromone Analogues of Protoschinia scutosa[J].Scientia Agricultura Sinica, 2022, 55(9): 1790-1799.

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References 35

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性信息素类似物 Sex pheromone analogue	剂量Dose (μg)
性信息素类似物 Sex pheromone analogue	0.1	1	10	100	1000
K1	A1	A2	A3	A4	A5
K2	B1	B2	B3	B4	B5
K3	C1	C2	C3	C4	C5
K4	D1	D2	D3	D4	D5
K5	E1	E2	E3	E4	E5
K6	F1	F2	F3	F4	F5

性信息素类似物 Sex pheromone analogue	直接刺激EAG相对响应值EAG relative response value of direct stimulation (m<BOLD>V</BOLD><BOLD>)</BOLD>
性信息素类似物 Sex pheromone analogue	0.001 μg·μL^-1	0.01 μg·μL^-1	0.1 μg·μL^-1	1 μg·μL^-1	10 μg·μL^-1	100 μg·μL^-1
K1	0.07±0.02c	0.13±0.003c	0.14±0.03c	0.29±0.04bc	0.44±0.07b	1.34±0.09a
K2	0.04±0.05d	0.16±0.07cd	0.20±0.02cd	0.31±0.07bc	0.51±0.07ab	0.72±0.04a
K3	0.05±0.01c	0.11±0.09bc	0.15±0.06bc	0.27±0.06bc	0.42±0.09ab	0.75±0.08a
K4	0.04±0.03d	0.11±0.05d	0.24±0.05cd	0.34±0.02bc	0.56±0.06ab	0.75±0.06a
K5	0.06±0.01d	0.18±0.01cd	0.23±0.02c	0.29±0.02b	0.38±0.03a	0.67±0.05a
K6	0.08±0.11ab	0.08±0.04ab	-0.04±0.17b	-0.12±0.17b	0.34±0.16ab	0.57±0.07a

性信息素类似物 Sex pheromone analogue	平均诱捕数量/诱捕器/15 d Average number of trapped adults/trap/15 d
性信息素类似物 Sex pheromone analogue	性信息素SP	0.1 μg	1 μg	10 μg	100 μg	1000 μg
K1	14.00±2.00bc	8.00±2.08c	11.67±1.45bc	32.33±0.67a	18.67±1.45b	12.00±2.08bc
K2	10.00±2.31a	7.33±3.53a	14.33±3.84a	14.67±7.51a	13.33±3.71a	8.67±3.33a
K3	3.00±1.00a	11.33±2.73a	8.67±3.53a	4.67±2.73a	3.67±2.03a	1.67±0.33a
K4	9.00±3.21a	15.67±4.81a	8.67±0.33a	6.33±1.76a	6.00±0.58a	4.67±2.33a
K5	16.00±3.21bc	8.67±0.88c	11.67±1.45bc	16.67±1.20bc	35.00±4.62a	22.33±1.76b
K6	7.67±2.03a	20.00±4.16a	16.67±2.67a	7.33±3.53a	13.33±3.71a	9.33±2.67a

Synthesis and Bioactivity of Sex Pheromone Analogues of Protoschinia scutosa

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