Synthesis of Sex Pheromone Candidates of Apocheima cinerarius Erschoff and Screening of the Activity
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- Ξάνθιππος Βονόρτας
- 7 χρόνια πριν
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1 AGROCHEMICALS Vol. 52, No. 3 Mar. 20,,,. [J]., 20, 52(3): , ( ) GC EAD GC EAD Z4 14 OAc Z6 14 OAc Z4 14 OAc Z6 14 OAc TQ460.3 A (20) Synthesis of Sex Pheromone Candidates of Apocheima cinerarius Erschoff and Screening of the Activity LAI Xiao-qian 1,2, YAN Qi 1, WEI Wei 3, HOU Xue-ling 1, MA Ji-xuan 1 (1.The Key Laboratory of Chemistry of Plant Resources in Arid Regions, Xinjiang Technical Institute of Physics and Chemistry, Chinese Academy of Sciences, Ürümqi , China; 2.University of Chinese Academy of Sciences, Beijing , China; 3.State Key Laboratory of Integrated Management of Pest Insects and Rodents, Institute of Zoology, Chinese Academy of Sciences, Beijing , China) Abstract: [Aims] The paper aims to further determine active ingredients of the sex pheromone and chemical structures thereof of Apocheima cinerarius by screening the analogues of A. cinerarius, which is significant for the future elicitation experiments and is helpful for non-pollution control of diseases and insect pests. [Methods] According to the previous research, the active ingredients of the sex pheromone of A. cinerarius have been proved to be tetradecenyl acetate. By synthesizing a serious of tetradecenyl acetates and using GC-EAD method, the position of double bond and configuration were determined. [Results] The GC-EAD spectrogram indicated that sensitive reaction of male moth antenna was detected to Z4-14 OAc and Z6-14 OAc. [Conclusions] Z4-14 OAc and Z6-14 OAc are the active ingredients of the sex pheromone of A. cinerarius. Key words: Apocheima cinerarius Erschoff; sex pheromone; active ingredients; screening 2000 [1] [2] [3] [4] [5] GC EAD GC MS GC EAD ( ) (O ) (1987 ) laixubing@yeah.net xlhou@ms.xjb.ac.cn
2 AGROCHEMICALS NMR VARIAN 400 MR TMS CDCl 3 YANAGIMOTO MFG, CO. YANO DHJF 4002 THP DHP 3, a~4d ( 4c ) 1) 2 (5 ) (2c) 1.5 g g PTS 20 ml CH 2 Cl g DHP CH 2 Cl 2 10 ml TLC 10 ml 1% NaOH MgSO g 2 (5 ) (2c) 82% 1 H NMR(CDCl 3, 400 MHz) δ 1.66~1.43(m 8H 4 CH 2 ) 1.72~1.68(m 1H OCH CH 2 ) 1.89~1.74(m 3H CH 2 CH 2 Br OCH 2 CH 2 ) 3.39(m 3H OCH CH 2 Br) 3.44(m 1H OCH 2 ), 3.77(m, 1H, OCH 4a~4d 7e~7h 6i 6j 2 ) 3.87(m, 1H, OCH 2 ), 4.58(m 1 1H OCHO ) C NMR(CDCl MHz) δ ( OCHO ) 67.42( OCH 2 ) 62.58( OCH 2 ) 33.96( CH 2 Br) 32.82(C 4 ) 30.95( OCHCH 2 ) ) 2 (6 ) (3c) ml 0.63 g 1 1 h 5 ml 1 g 2c HMPA a.dhp/ch 2Cl 2 b. n -BuLi/HMPA/THF c.ni(ch 3COO) 2/NaBH 4/H 2/ C 2H 5OH d. CH 3COCl/CH 3COOH 2 a.phch 3/PPh 3 b. n -BuLi/THF c.hbr(40%)/phch 3 d.ac 2O/Et 3N/ CH 2Cl 2 e. C 5H 5NO/Na 2CO 3/CH 2Cl 2 f. n-buli/thf 3 10 ml 2 MgSO g 2 (6 ) (3c) 83% 1 H NMR(CDCl MHz) δ 0.88(t J=6.8 Hz 3H CH 3 ) 1.33~1.28(m 6H 3 CH 2 ) 1.50~1.34(m 8H 4 CH 2 ) 1.64~1.52(m 8H 4 CH 2 ) 1.70(m 1H OCHCH 2 ) 1.84(m 1H OCHCH 2 ) 2.08(m 1H C CCH 2 ) 2.31(m 1H C CCH 2 ) 3.39(m 1H OCH 2 ) 3.49(m 1H OCH 2 ) 3.86(m 1H OCH 2 ) 3.73(m 1H OCH 2 ) 4.56(m 1H OCHO ) C NMR(CDCl MHz) δ 99.05( OCHOH ) 88.42( C C ) 69.17( C C ) 67.78( OCH 2 ) 62.54( OCH 2 ) 35.19(C 12 ) (C 8 ) 14.29(C 14 ) 3) Z6 14 OAc(4c) 0.65 g H 2 15 ml 0.16 g NaBH 4 8 min 0.8 ml 10 min 0.8 g 3c a.dhp/pts/ch 2Cl 2 b. n -BuLi/C 10H 21Br/HMPA/N 2 c.pts/ch 3OH d. NaH/1,3 e. DHP/CH 2Cl 2 f.buli/ch 3I/N 2/ 20 g. Na/NH 3(liquid)/ 78 h. Ni(CH 3COO) 2 4H 2O/NaBH 4/H 2/C 2H 5OH i. CH 3COCl/CH 3COOH 0.77 g 2 (Z6 ) 0.77 g 2 (Z6 )
3 15 ml 0.68 g 5 h 5% 0.5 g Z6 14 OAc(4c) 76% 4a 4b 4d 4c 4a 70% 1 H NMR(CDCl MHz) δ 0.87(t J =6.8 Hz 3H) 1.43~1.22(m 14H 7 CH 2 ) 1.69~1.65(m 2H OCH 2 CH 2 ) 2.05~1.98(m 4H CH 2 CH=CHCH 2 ) 2.06(s 3H CH 3 ) 4.07(t J=6.8 Hz 2H OCH 2 ) 5.29~5.45(m 2H CH=CH ) C NMR(CDCl MHz) δ (C=O) 1.42(C=C) (C=C) 64.24( OCH 2 ) 32.12(C 12 ) (C 3 ) 22.92(C ) b 72% 1 H NMR(CDCl MHz) δ 0.88(t J=6.8 Hz 3H CH 3 ) 1.35~1.23(m 12H 6 CH 2 ) 1.46(m 2H CH 2 ) 1.67(m 2H OCH 2 CH 2 ) 2.03~1.97(m 4H CH 2 CH=CHCH 2 ) 2.06(s 3H CH 3 ) 4.07(t J =6.8 Hz 2H OCH 2 ) 5.32~5.43(m 2H CH=CH ) C NMR(CDCl MHz) δ (C=O) 1.38(C=C) (C=C) 64.20(C 1 ) 32.11(C 12 ) (C 3 ) 21.16(C ) 14.29( CH 3 ) 4c 76% 1 H NMR(CDCl MHz) δ 0.89(t J=6.8 Hz 3H) 1.37~1.28(m 12H) 1.43~1.39(m 2H) 1.63~1.55(m 2H) 2.03~1.98(m 4H CH=CHCH 2 ) 2.05(s 3H CH 3 ) 4.06(t J =6.8 Hz 2H OCH 2 ) 5.33~5.39(m 2H CH=CH ) C NMR(CDCl MHz) δ (C=O) 0.50(C=C) (C=C) 64.81(C 1 ) 32.08(C 12 ) ( CH 3 ) 4d 77% 1 H NMR(CDCl MHz) δ 0.87(t J =6.8 Hz 3H) 1.43~1.28(m 14H 7 CH 2 ) 1.64(m 2H) 2.03~1.88(m 4H 2CH=CHCH 2 ) 2.05(s 3H CH 3 ) 4.07(t J=6.8 Hz 2H) 5.32~5.40(m 2H) C NMR(CDCl MHz) δ (C=O) 0.35(C=C) (C=C) 64.85(C 1 ) 32.12(C 12 ) (C 6 ) 27.14(C 9 ) 26.06(C 3 ) e~7h ( 7g ) 1) (2g) 1.35 g g PPh 3 30 ml 8 h 10 ml g (2g) m.p. 241~243 76% 2) 10 (5g) 4.5 g 1, ml ml (40%) h 90 2 ml (40%) g ml 2.64 g ml CH 2 Cl g 2.10 g 5 ml CH 2 Cl 2 6 h 1 ml CH 2 Cl 2 5 ml NaHCO 3 NaCl MgSO g 10 (5g) 91.7% 1 H NMR(CDCl MHz) δ 1.38~1.21(m 12H 6 CH 2 ) 1.58(m 2H OCH 2 CH 2 ) 1.85(m 2H CH 2 CH 2 Br) 2.05(s 3H CH 3 ) 3.41(t J=6.8 Hz 2H CH 2 Br) 4.05(t J=6.8 Hz 2H OCH 2 ) C NMR(CDCl MHz) δ (C=O) 64.84( OCH 2 ) 33.01( CH 2 Br) ( CH 3 ) 3) 10 (6g) 50 ml 1.0 g 5 g g g NaHCO 3 20 ml 8 h g 6g 27.6% 1 H NMR(CDCl MHz) δ 1.30(m 10H 5 CH 2 ) 1.60(m 2H CH 2 CH 2 O ) 1.62(m 2H CH 2 CH 2 CHO) 2.04(s 3H CH 3 ) 2.42(t J=7.2 Hz 2H) 4.05(t J =7.2 Hz 2H OCH 2 ) 9.76(t J =1.2 Hz 1H CHO) C NMR(CDCl MHz) δ ( CHO) ( COCH 3 ) 64.55( OCH 2 ) 44.05( CH 2 CHO) ) (Z/E)10 14 OAc(7g) 10 ml THF 0.52 g 2 g 0.8 ml 1 h 0.2 g 6 g 3 ml THF TLC NH 4 Cl NaCl MgSO g (Z/E)10 14 OAc(7g) 71.8% 7e 7f 7h 7g GC MS 7e Z/E 99/1 7f Z/E 99/1 7g Z/E 93/2 7h Z /E 19/61 7e 69% 1 H NMR(CDCl MHz) δ 0.87(t J=6.8 Hz 3H CH 3 ) 1.37~1.18(m 14H 7 CH 2 ) 1.60(m 2H OCH 2 CH 2 ) 2.02~1.85(m
4 4H CH 2 CH=CHCH 2 ) 2.04(s 3H CH 3 ) 4.05(t J=6.8 Hz 2H OCH 2 ) 5.35(m 2H CH=CH ) C NMR(CDCl MHz) δ (C=O) 0.27(C=C) (C 1 ) 31.75(C 12 ) (C 7 ) 27.37(C 10 ) (C 14 ) 7f 75% 1 H NMR(CDCl MHz) δ 0.87(t J=7.4 Hz 3H CH 3 ) 1.38~1.21(m 14H 7 CH 2 ) 1.61(m 2H OCH 2 CH 2 ) 2.03~1.92(m 4H CH 2 CH=CHCH 2 ) 2.04(s 3H CH 3 ) 4.05(t J=6.8 Hz 2H OCH 2 ) 5.36(m 2H CH=CH ) C NMR(CDCl MHz) δ (C=O) 0.15(C=C) (C 1 ) (C 8 ) 27.14(C 11 ) 26.12(C 3 ) (C 14 ) 7g 72% 1 H NMR(CDCl MHz) δ 0.91(t J=7.4 Hz 3H CH 3 ) 1.38~1.18(m 14H 7 CH 2 ) 1.57(m 2H OCH 2 CH 2 ) 2.04~1.97(m 4H CH 2 CH=CHCH 2 ) 2.05(s 3H CH 3 ) 4.06(t J =6.8 Hz 2H OCH 2 ) 5.36~5.38(m 2H CH=CH ) AGROCHEMICALS C NMR(CDCl MHz) δ (C=O) 0.27(C=C) (C 9 ) ( CH 3 C=O) h 71% 1 H NMR(CDCl MHz) δ 0.95(t J=7.4 Hz 3H) 1.34~1.20(m 14H 7 CH 2 ) 1.61(m 2H OCH 2 CH 2 ) 2.08~1.92(m 4H CH 2 CH=CHCH 2 ) 2.05(s 3H CH 3 ) 4.06(t J=6.8 Hz 2H OCH 2 ) 5.43~5.34(m 2H CH=CH ) C NMR(CDCl MHz) δ (C=O) 1.75(C=C) (C 1 ) 32.57(C 9 ) (C 14 ) i 6j 1) 1 2 (2i) 1.88 g 15 ml CH 2 Cl g PTS 2.8 g DHP CH 2 Cl 2 5 ml 10 ml 5 ml 1% NaOH 5 ml MgSO 4 4. g 2 (2 ) 88% 1 H NMR(CDCl MHz) δ 1.62~1.47(m 4H 2CH 2 ) 1.91~1.65(m 2H CH 2 ) 2.42(t J =2.4 Hz 1H C CH) 3.54(m 1H OCH 2 ) 3.85(m 1H OCH 2 ) 4.32~4.21(m 2H OCH 2 ) 4.83(t J =3.2 Hz 1H) C NMR(CDCl MHz) δ ( C CH) ( OCH 2 ) 56.43( CH 2 C CH) ml 15 ml THF 1.8 g 2 (2 ) 30 6 ml h 2.88 g 1 HMPA 10 ml 0.5 h NH 4 Cl 3.4 g 2 (2 ) 3.4 g 20 ml 0.5 g PTS 3 h 15 ml NaHCO 3 (5%) 15 ml g 1 2 (2i) 83% 1 H NMR(CDCl MHz) δ 0.88(t J=6.8 Hz 3H CH 3 ) 1.30~1.21(m 12H 6 CH 2 ) 1.36(m 2H CH 3 CH 2 ) 1.57(s 1H OH) 1.45~1.52(m 2H CH 2 CH 2 C C ) 2.22~1.21(m 2H C CCH 2 ) 4.25(t J =1.4 Hz 2H CH 2 OH) C NMR(CDCl MHz) δ 86.73(C 3 ) 78.31(C 2 ) 51.48(C 1 ) 31.91(C 11 ) (C 4 ) 14.09(C ) 2) 1 12 (3i) 2 g NaH 20 ml 70 3 h g 2i 15 ml 3 h NaHCO g 1 12 (3i) 62.1% 1 H NMR(CDCl MHz) δ 1.43~1.25(m 14H 7 CH 2 ) 1.56~1.45(m 4H 2 CH 2 ) 1.90(t J=1.6 Hz 1H C CH) 2.16(s 1H OH) 2.41~2.22(m 2H CH 2 C CH) 3.64(t J=6.8 Hz 2H CH 2 OH) C NMR(CDCl MHz) δ 84.80( C CH) 68.04( C CH) 63.11( CH 2 OH) 32.84(C 2 ) (C 3 ) 18.42(C 11 ) 3) 2 (12 ) (4i) 10 ml CH 2 Cl g 3i 0.02 g PTS 50 ml 0.53 g DHP CH 2 Cl h 10 ml Na 2 CO 3 (5%) 10 ml 1.54 g 2 (12 ) 88% 250 ml 20 ml THF 1.54 g 2 (12 ) ml h 0.9 g CH 3 I THF 10 ml 0.5 h 3 h NH 4 Cl 1.55 g 4i 96%
5 4) 2 (E12 ) (5i) 250 ml ml 0.5 g 1 h g 4i THF 3 ml 1 h NH 4 Cl g 2 (E12 ) (5i) 97% 5) 2 (Z12 ) (5j) 0.62 g 20 ml H g NaBH 4 5 ml 8 min 0.65 ml 10 min g 4i 5 ml g 2 (Z 12 ) (5j) 96% 6) E12 14 OAc(6i) Z12 14 OAc(6j) g 5i g 5j 2 50 ml 15 ml 2 ml 60 5 h Na 2 CO 3 (5%) MgSO g E12 14 OAc(6i) 0.40 g Z12 14 OAc(6j) 80% 6i 80% 1 H NMR(CDCl MHz) δ 5.40(m 2H CH=CH ) 4.07(t J=6.8 Hz 2H CH 2 OAc) 2.05(s 3H COCH 3 ) 1.95(m 2H CH 2 CH=CH ) 1.64(m 2H CH 2 CH 2 O ) 1.62(d J=6.8 Hz 3H CH 3 ) 1.38~1.20(m 16H 8 CH 2 ) C NMR(CDCl MHz) δ (C=O) 1.64( HC=CH ) ( HC=CH ) 64.64(C 1 ) 32.59(C 11 ) (C 14 ) 6j 80% 1 H NMR(CDCl MHz) δ 5.41(m 2H CH=CH ) 4.05(t J=6.8 Hz 2H CH 2 OAc) 2.04(s 3H COCH 3 ) 2.03(m 2H CH 2 CH=CH ) 1.65(d J=6.8 Hz 3H CH 3 ) 1.61(m 2H CH 2 CH 2 O ) 1.35~1.21(m 16H 8 CH 2 ) C NMR(CDCl MHz) δ ( C=O) 0.82( HC=CH ) ( HC=CH ) 64.60(C 1 ) (C 11 ) 25.88(C 3 ) (C 14 ) 2 EAG (PRG 2) 2 EAG HP 5 (30 m 0.25 mm 0.25 μm J&W Scientice Folsom CA) (OSS 2 SGE ) 1 2 FID (EAD) GC EAD (Syntech The Netherlands) GC EAD GC EAD 3 3 A 4a 4b 4c B 4d 7e 7f C 7g 7h 6i 6j 3 GC EAD 3 1 A A 4a 4b 4c GC EAD B B 4d 7e 7f GC EAD C C 7g 7h 6i 6j GC EAD D B C 4d 7e 7f 7g 7h 6i 6j GC EAD 1 GC EAD GC EAD A B C EAD B C A Z4 14 OAc Z5 14 OAc Z6 14 OAc GC EAD 2 Agilent Technologies 7890A Syntech (GC EAD) 2~3 d 0.5 mm 10 mm (E) Z 4 14 OAc(4a) GC EAD (F) Z 6 14 OAc(4c) GC EAD 2 GC EAD
6 AGROCHEMICALS 1 2 Z4 14 OAc(4a) Z 6 14 OAc(4c) Z 5 14 OAc(4b) GC EAD [5] 2 Z4 14 OAc Z6 14 OAc 2 3 TypeI [6-7] 4 12 Wittig 7 ( 1) 4 Z 4 14 OAc(4a) Z 5 14 OAc(4b) Z 6 14 OAc(4c) Z7 14 OAc(4d) Wittig ( 2) (Z /E )8 14 OAc(7e) (Z /E )9 14 OAc(7f) (Z /E )10 14 OAc(7g) (Z/E)11 14 OAc(7h) 8 Z OAc(6i) E OAc(6j)( 3) GC EAD min Z4 14 OAc Z6 14 OAc GC EAD [22],,,. Bacillus cereus W2 6 [J]., 1998, 11(3): [23] TANG Wen-hua. Advances in Biological Control of Plant Diseases: Proceeding of the International Workshop on Biological Control of Plant Diseases[M]. Beijing: China Agricultural University Press, [24]. A 47 ( )[D]. :, [25] ( )[D]. :, [26],,,. [J]., 2007, 6(4): [27],,. [M]. :, [28],,,. APS 1 4 [5] GC MS [8] 4 12 GC EAD Z4 14 OAc Z6 14 OAc [1],,,. [J]., 2008, 20(5): [2]. [M]. :, 1992: [3],,. [J]., 2010, 29(1): [4],. Bt [J]., 2006, 25(3): [5],,,. GC MS [J]., 2011, 54(3): [6] ANDO T. Sex Pheromones of Moths[BD/OL]. ( ) [ ]. /~antetsu /LepiPheroList.htm. [7] HO H Y, HUNG C C, CHUANG T H, et al. Identification and Synthesis of the Sex Pheromone of the Passionvine Mealybug, Planococcus Minor(Maskell)[J]. J Chem Ecol, 2007, 33(10): [8] ANDO T, YAMAKAWA R. Analyses of Lepidopteran Sex Pheromones by Mass Spectrometry[J]. Trends Analytical Chemistry, 2011, 30(7): [J]., 1999, 39(4): [29],,. [C]. 2009, 2009: [30],,. B8 [J]., 2007, 23(1): [31],,. [J]., 1994, 18(2): [32],,,. (ANTI 8098A) (gfp) [J]., 2010, 18(2): [33]. C332 ( )[D]. :, 2007.
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