Spectral Analysis of Fungicide Cyflufenamid

doi:10.11938/cjmr20160114

Abstract

Abstract:

Cyflufenamid is an excellent fungicide with novel molecular structure. In this paper, one-dimensional and two-dimensional NMR spectroscopy, combined with mass spectrometry (MS), ultraviolet spectroscopy (UV) and infrared spectroscopy (IR), were used to elucidate the structure of cyflufenamid. NMR chemical shifts of the compound were assigned. The correspondences between the UV/IR absorption peaks and the functional groups in this compoundwere discussed. The effects of the fluorine atoms in the compound on the ¹H and ¹³C NMR chemical shifts were investigated, as well as the possible fragmentation patterns of the compound.

Key words: Liquid-state NMR, assignment, cyflufenamid, mass spectroscopy

CLC Number:

O482.53

LIU De-yun, WANG Ya-ru, WEI Hai-feng, XIA Gao-feng, YANG Xiao-yun. Spectral Analysis of Fungicide Cyflufenamid[J]. Chinese Journal of Magnetic Resonance, 2016, 33(1): 142-152.

References

[1] Ma Yun-sheng(马韵升), Liu Chang-ling(刘长令). Cyflufenamid-a new powdery mildew fungicide(新型白粉病杀菌剂环氟菌胺)[J]. Chinese J Pest(农药), 2005, 44 (3): 128－129.

[2] Kasahara I, Ooka H, Sano S, et al. Benzamidoxime derivative, process for production thereof, and agrohorticultural bactericide: EP, 0805148 [P]. 1997-05-11.

[3] Masahiro H, Homare Y, Hiroyasu H, et al. Control efficacy of cyflufenamid in the field and its fungicidal properties[J]. Pestic Sci, 2006, 31 (2): 116－122.

[4] Masahiro H, Homare Y, Hiroshi S, et al. Fungicidal activities of cyflufenamid against various plant-pathogenic fungi[J]. Pestic Sci, 2006, 31 (2): 95－101.

[5] Cheng Zhi-ming(程志明). Development of a novel fungicide, cyflufenamid(杀菌剂环氟菌胺的开发)[J]. World Pesticides(世界农药), 2007, 29 (6): 1－5.

[6] Zhu Li-ping(朱莉萍), Zhu Tao(朱涛), Pan Yu-xiang(潘玉香), et al. Determination of different kinds of pesticide residues in vegetable by gas-chromatography(气相色谱法同时测定蔬菜及水果中多种农药残留量)[J]. Chinese J Anal Chem(分析化学), 2008, 36 (7): 999－1003.

[7] Li Li(李立), Lou Xi-shan(娄喜山), Fu Jian(付建). Method for the gas chromatography-mass spectrometry detection on certral amine residue of fluoride of food(食品中环氟菌胺残留量的气相色谱-质谱联用检测方法的研究)[J]. Food Science and Technology(食品科学与技术), 2008, 33 (11): 271－274.

[8] Chen Xiao-long(陈小龙), Li Zheng-xiang(李正翔), Cao Zhao-yun(曹赵云), et al. Dtermination of six novel aminde fungicide in vegetables and fruits by liquid chromatography-tandem mass spectrometry(液相色谱-串联质谱法测定蔬菜和水果中6种新型酰胺类杀菌剂的残留量)[J]. Chinese J Chrom(色谱), 2013, 31 (10): 954－960.

[9] Yang Xiu-wei(杨秀伟), Wu Qi(吴琦), Zou Lei(邹磊), et al. Characterization of NMR signals of tanacetin and artesin isolated from the whole herbs of Crossostephium chinense(芙蓉菊中艾菊素和草蒿素结构的NMR信号表征)[J]. Chinese J Magn Reson(波谱学杂志), 2008, 25 (1): 117－127.

[10] Peng Shuang(彭双), Han Li-feng(韩立峰), Liu Er-wei(刘二伟) , et al. NMR characterization of two flavonyl glycosides isolated from drnaria fortune(骨碎补中2个黄酮苷类化合物的NMR研究)[J]. Chinese J Magn Reson(波谱学杂志), 2013, 30 (1): 140－147.

[11] Adnan J, Al-Rehaily A, Mohammad S, et al. Solanopubamine, a rare steroidal alkaloid from Solanum schimperianum: Synthesis of some new alkyl and acyl derivatives, their anticancer and antimicrobial evaluation[J]. J Saudi Chem Soc, 2013, 17(1): 67－76.

[12] Liu Hai-bo(刘海波), Xu Ming(许明), Yuan Ling(袁玲). Spectroscopic characterization of a quinolinone compound with terminal of ethynyl(一种含末端炔喹啉酮类化合物的波谱学研究)[J]. Chinese J Magn Reson(波谱学杂志), 2013, 30 (4): 594－601.

[13] Wei Yu-hai(魏玉海), Yao Zhi-min(姚志敏), Feng Xiao-bo(凤晓博), et al. NMR assignment of metominostrobin and its Z-isomer(苯氧菌胺及其Z-异构体的NMR数据全归属)[J]. Mod Agroch(现代农药), 2014, 13 (1): 19－21.

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