Synthesis and biological evaluation of novel N-pyridylpyrazole derivatives containing 1,2,3-triazole moieties

Based on the commercial insecticide chlorantraniliprole, a series of novel N-pyridylpyrazole derivatives containing 1,2,3-triazole moieties were designed and synthesized via Huisgen cycloaddition reaction. The insecticidal activities of the new compounds against the oriental armyworm (Mythimna separ...

Full description

Saved in:
Bibliographic Details
Published inJournal of Pesticide Science Vol. 40; no. 3; pp. 138 - 142
Main Authors Mao, Mingzhen, Li, Yuxin, Liu, Qiaoxia, Xiong, Lixia, Zhang, Xiao, Li, Zhengming
Format Journal Article
LanguageEnglish
Published Tokyo Pesticide Science Society of Japan 01.01.2015
Japan Science and Technology Agency
Subjects
Online AccessGet full text

Cover

Loading…
Abstract Based on the commercial insecticide chlorantraniliprole, a series of novel N-pyridylpyrazole derivatives containing 1,2,3-triazole moieties were designed and synthesized via Huisgen cycloaddition reaction. The insecticidal activities of the new compounds against the oriental armyworm (Mythimna separata) were evaluated, of which compound Ib with an N-isopropyl anthranilic amide moiety displayed 100% larvicidal activities against Mythimna separata at a concentration of 10 mg/L. Moreover, the fungicidal activities of some target compounds in vitro against five fungi at 50 µg⁄mL indicated that some compounds exhibited moderate fungicidal activities.
AbstractList Based on the commercial insecticide chlorantraniliprole, a series of novel N-pyridylpyrazole derivatives containing 1,2,3-triazole moieties were designed and synthesized via Huisgen cycloaddition reaction. The insecticidal activities of the new compounds against the oriental armyworm (Mythimna separata) were evaluated, of which compound Ib with an N-isopropyl anthranilic amide moiety displayed 100% larvicidal activities against Mythimna separata at a concentration of 10 mg/L. Moreover, the fungicidal activities of some target compounds in vitro against five fungi at 50 µg/mL indicated that some compounds exhibited moderate fungicidal activities.
Based on the commercial insecticide chlorantraniliprole, a series of novel N-pyridylpyrazole derivatives containing 1,2,3-triazole moieties were designed and synthesized via Huisgen cycloaddition reaction. The insecticidal activities of the new compounds against the oriental armyworm (Mythimna separata) were evaluated, of which compound Ib with an N-isopropyl anthranilic amide moiety displayed 100% larvicidal activities against Mythimna separata at a concentration of 10 mg/L. Moreover, the fungicidal activities of some target compounds in vitro against five fungi at 50 mu g/mL indicated that some compounds exhibited moderate fungicidal activities.
Based on the commercial insecticide chlorantraniliprole, a series of novel N-pyridylpyrazole derivatives containing 1,2,3-triazole moieties were designed and synthesized via Huisgen cycloaddition reaction. The insecticidal activities of the new compounds against the oriental armyworm (Mythimna separata) were evaluated, of which compound Ib with an N-isopropyl anthranilic amide moiety displayed 100% larvicidal activities against Mythimna separata at a concentration of 10 mg/L. Moreover, the fungicidal activities of some target compounds in vitro against five fungi at 50 μg/mL indicated that some compounds exhibited moderate fungicidal activities.
Author Zhang, Xiao
Mao, Mingzhen
Liu, Qiaoxia
Xiong, Lixia
Li, Zhengming
Li, Yuxin
Author_xml – sequence: 1
  fullname: Mao, Mingzhen
  organization: Xi’an Modern Chemistry Research Institute
– sequence: 2
  fullname: Li, Yuxin
  organization: State Key Laboratory of Elemento-Organic Chemistry, Institute of Elemento-Organic Chemistry, Nankai University
– sequence: 3
  fullname: Liu, Qiaoxia
  organization: State Key Laboratory of Elemento-Organic Chemistry, Institute of Elemento-Organic Chemistry, Nankai University
– sequence: 4
  fullname: Xiong, Lixia
  organization: State Key Laboratory of Elemento-Organic Chemistry, Institute of Elemento-Organic Chemistry, Nankai University
– sequence: 5
  fullname: Zhang, Xiao
  organization: State Key Laboratory of Elemento-Organic Chemistry, Institute of Elemento-Organic Chemistry, Nankai University
– sequence: 6
  fullname: Li, Zhengming
  organization: State Key Laboratory of Elemento-Organic Chemistry, Institute of Elemento-Organic Chemistry, Nankai University
BookMark eNp9UU1v1DAQtVCRKEvvHCNx4dCUcWwnzhGVtiBVcAAkbpbjTLZeOfZiZ1cKvx6nKa3UA5I1M4f3MZ73mpz44JGQtxQuqJD8w26PabImXXyiooQKXpBTynhbQluxk_tZlkK2v16Rs5R2AEAb1rRtfUrG77Of7jDZVGjfF50NLmyt0a7Ao3YHPdngizAUPhzRFV_L_RxtP7vc9J_gsOgx2mNGHTEVJvhJW2_9tqDn1Tkrp2hX1BgsThbTG_Jy0C7h2UPfkJ_XVz8uP5e3326-XH68LY0AmEqJXQeMDd1gGtroWgjONQKvRdvrRsteYtO1fAAm6FAzJlD0rDNdr3X-m-RsQ96vuvsYfh_ybdRok0HntMdwSIo2tRS1ZPltyLtn0F04RJ-3y6hs3FY0H3FD6hVlYkgp4qCMne6PM0VtnaKgliDUvyBUDkLlIDIRnhH30Y46zv-j3KyUEfslieCd9fi0lpnZwjGqgoUBHIApyHJAmcyFV5WoRY43K12vSrs06S0-WuuYDR0-WXNQbCkPKzwCzJ2OCj37C1auwf8
CitedBy_id crossref_primary_10_3390_molecules21081020
crossref_primary_10_3987_COM_18_13944
crossref_primary_10_1515_ncrs_2016_0150
crossref_primary_10_1002_jhet_3505
crossref_primary_10_1002_slct_201903254
crossref_primary_10_1515_hc_2022_0177
Cites_doi 10.1016/j.bmcl.2012.11.045
10.1002/ps.2329
10.1002/ardp.200900317
10.1002/med.20107
10.1021/jo0487956
10.1021/jf500003d
10.1002/cjoc.201180295
10.1021/jf102842r
10.1016/j.bmc.2009.01.018
10.1016/j.bmcl.2008.12.026
10.1002/1521-3773(20020715)41:14<2596::AID-ANIE2596>3.0.CO;2-4
10.1002/cjoc.201200362
10.1016/j.tetasy.2009.03.021
ContentType Journal Article
Copyright 2015 Pesticide Science Society of Japan
Copyright Japan Science and Technology Agency 2015
Copyright_xml – notice: 2015 Pesticide Science Society of Japan
– notice: Copyright Japan Science and Technology Agency 2015
CorporateAuthor Institute of Elemento-Organic Chemistry
State Key Laboratory of Elemento-Organic Chemistry
Nankai University
Xi'an Modern Chemistry Research Institute
CorporateAuthor_xml – name: State Key Laboratory of Elemento-Organic Chemistry
– name: Institute of Elemento-Organic Chemistry
– name: Xi'an Modern Chemistry Research Institute
– name: Nankai University
DBID AAYXX
CITATION
7SS
7ST
7TK
7U7
C1K
SOI
DOI 10.1584/jpestics.D15-020
DatabaseName CrossRef
Entomology Abstracts (Full archive)
Environment Abstracts
Neurosciences Abstracts
Toxicology Abstracts
Environmental Sciences and Pollution Management
Environment Abstracts
DatabaseTitle CrossRef
Entomology Abstracts
Toxicology Abstracts
Neurosciences Abstracts
Environment Abstracts
Environmental Sciences and Pollution Management
DatabaseTitleList Entomology Abstracts

Entomology Abstracts

DeliveryMethod fulltext_linktorsrc
Discipline Agriculture
EISSN 1349-0923
EndPage 142
ExternalDocumentID 3916679681
10_1584_jpestics_D15_020
cy3jpesc_2015_004003_010_0138_01422565799
article_jpestics_40_3_40_D15_020_article_char_en
GroupedDBID 29L
5GY
AAFWJ
ACGFO
AEGXH
AFPKN
ALMA_UNASSIGNED_HOLDINGS
GX1
HH5
JSF
JSH
P2P
RJT
RNS
2WC
7.U
A8Z
ABDBF
ACIWK
ACPRK
ACUHS
AENEX
AFRAH
B.T
CS3
E3Z
EBD
EBS
ECGQY
EJD
ESX
GROUPED_DOAJ
HYE
JMI
KQ8
MOJWN
N5S
OK1
RPM
RZJ
TKC
TUS
XSB
~8M
AAYXX
CITATION
OVT
7SS
7ST
7TK
7U7
C1K
SOI
ID FETCH-LOGICAL-c500t-8ebb033fbfc717a65544ae04659da7a8d8e7b94f0351f6335e5d3bcbdaa000843
ISSN 1348-589X
IngestDate Fri Jul 11 00:48:48 EDT 2025
Mon Jun 30 08:35:59 EDT 2025
Tue Jul 01 03:55:21 EDT 2025
Thu Apr 24 22:52:58 EDT 2025
Thu Jul 10 16:12:17 EDT 2025
Thu Aug 17 20:29:47 EDT 2023
IsDoiOpenAccess true
IsOpenAccess true
IsPeerReviewed true
IsScholarly true
Issue 3
Language English
LinkModel OpenURL
MergedId FETCHMERGED-LOGICAL-c500t-8ebb033fbfc717a65544ae04659da7a8d8e7b94f0351f6335e5d3bcbdaa000843
Notes ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 14
content type line 23
OpenAccessLink https://www.jstage.jst.go.jp/article/jpestics/40/3/40_D15-020/_article/-char/en
PQID 1755492192
PQPubID 1976368
PageCount 5
ParticipantIDs proquest_miscellaneous_1768568368
proquest_journals_1755492192
crossref_citationtrail_10_1584_jpestics_D15_020
crossref_primary_10_1584_jpestics_D15_020
medicalonline_journals_cy3jpesc_2015_004003_010_0138_01422565799
jstage_primary_article_jpestics_40_3_40_D15_020_article_char_en
ProviderPackageCode CITATION
AAYXX
PublicationCentury 2000
PublicationDate 2015-01-01
PublicationDateYYYYMMDD 2015-01-01
PublicationDate_xml – month: 01
  year: 2015
  text: 2015-01-01
  day: 01
PublicationDecade 2010
PublicationPlace Tokyo
PublicationPlace_xml – name: Tokyo
PublicationTitle Journal of Pesticide Science
PublicationTitleAlternate J. Pestic. Sci.
PublicationYear 2015
Publisher Pesticide Science Society of Japan
Japan Science and Technology Agency
Publisher_xml – name: Pesticide Science Society of Japan
– name: Japan Science and Technology Agency
References 3) B. L. Finkelstein, G. P. Lahm, S. F. McCann, Y. Song and T. M. Stevenson (E. I. Du Pont de Nemours and Company): WO 2003/016284 A1 (2003).
4) K. A. Hughes, G. P. Lahm, T. P. Selby and T. M. Stevenson (E. I. Du Pont de Nemours and Company): WO 2004/067528 A1 (2004).
8) Y. Zhao, Y. Q. Li, L. X. Xiong, H. X. Wang and Z. M. Li: Chin. J. Chem. 30, 1748–1758 (2012).
10) J. Wu, B.-A. Song, D.-Y. Hu, M. Yue and S. Yang: Pest Manag. Sci. 68, 801–810 (2012).
20) K. van Alem, G. Belder, G. Lodder and H. Zuilhof: J. Org. Chem. 70, 179–190 (2005).
5) R. G. Hall, O. Loiseleur, J. Pabba, S. Pal, A. Jeanguenat, A. Edmunds and A. Stoller: WO 2009/010260 A2 (2009).
19) Q. Feng, G. Yu, L. Xiong, M. Wang and Z. Li: Chin. J. Chem. 29, 1651–1655 (2011).
1) DuPont Rynaxypyr_insect control Technical Bulletin: http://www2.dupont.com/Production_Agriculture/en_US/assets/downloads/pdfs/ Rynaxypyr_Tech_Bulletin.pdf (Accessd 29 May, 2015
18) J. L. Randall, R. A. Gibbs, G. K. Bosch, M. D. Curtis, L. Sun and N. Nikolaides: US 2004/0167194 A1 (2004).
6) B. Li, D. Xiang, B. Chai, J. Yuan, H. Yang, H. Zhang, H. Wu and H. Yu: (Sinochem Corp., Shenyang Research Institute of Chemcal Industry Co. Ltd.): WO 2008/134969 A1(2008).
16) E. D. Chrysina, É. Bokor, K. Alexacou, M. Charavgi, G. N. Oikonomakos, S. E. Zographos, D. D. Leonidas, N. G. Oikonomakos and L. Somsák: Tetrahedron Asymmetry 20, 733–740 (2009).
12) G. D. Annis, B. J. Myers, T. P. Selby, T. M. Stevenson and W. T. Zimmerman (E. I. Du Pont de Nemours and Company): WO 2002/048115 A2 (2002).
15) N. G. Aher, V. S. Pore, N. N. Mishra, A. Kumar, P. K. Shukla, A. Sharma and M. K. Bhat: Bioorg. Med. Chem. Lett. 19, 759–763 (2009).
17) D. Raffa, O. Migliara, B. Maggio, F. Plescia, S. Cascioferro, M. G. Cusimano, G. Tringali, C. Cannizzaro and F. Plescia: Arch. Pharm. 343, 631–638 (2010).
9) M. Mao, Y. Li, Q. Liu, Y. Zhou, X. Zhang, L. Xiong, Y. Li and Z. Li: Bioorg. Med. Chem. Lett. 23, 42–46 (2013).
11) M.-Z. Mao, Y.-X. Li, Y.-Y. Zhou, X.-L. Zhang, Q.-X. Liu, F.-J. Di, H.-B. Song, L.-X. Xiong, Y.-Q. Li and Z.-M. Li: J. Agric. Food Chem. 62, 1536–1542 (2014).
21) V. V. Rostovtsev, L. G. Green, V. V. Fokin and K. B. Sharpless: Angew. Chem. Int. Ed. 41, 2596–2599 (2002).
7) Q. Feng, Z.-L. Liu, L.-X. Xiong, M.-Z. Wang, Y.-Q. Li and Z.-M. Li: J. Agric. Food Chem. 58, 12327–12336 (2010).
2) G. P. Lahm, D. Cordova and J. D. Barry: Bioorg. Med. Chem. 17, 4127–4133 (2009).
14) G. C. Tron, T. Pirali, R. A. Billington, P. L. Canonico, G. Sorba and A. A. Genazzani: Med. Res. Rev. 28, 278–308 (2008).
13) Z. Li, B. Wang, J. Zhang, J. Xu, L. Xiong, Y. Li, Y. Zhao and G. Wang (Nankai University): WO 2012/163095 A1(2012).
11
12
13
14
15
16
17
18
19
1
2
3
4
5
6
7
8
9
20
10
21
References_xml – reference: 7) Q. Feng, Z.-L. Liu, L.-X. Xiong, M.-Z. Wang, Y.-Q. Li and Z.-M. Li: J. Agric. Food Chem. 58, 12327–12336 (2010).
– reference: 8) Y. Zhao, Y. Q. Li, L. X. Xiong, H. X. Wang and Z. M. Li: Chin. J. Chem. 30, 1748–1758 (2012).
– reference: 21) V. V. Rostovtsev, L. G. Green, V. V. Fokin and K. B. Sharpless: Angew. Chem. Int. Ed. 41, 2596–2599 (2002).
– reference: 2) G. P. Lahm, D. Cordova and J. D. Barry: Bioorg. Med. Chem. 17, 4127–4133 (2009).
– reference: 19) Q. Feng, G. Yu, L. Xiong, M. Wang and Z. Li: Chin. J. Chem. 29, 1651–1655 (2011).
– reference: 13) Z. Li, B. Wang, J. Zhang, J. Xu, L. Xiong, Y. Li, Y. Zhao and G. Wang (Nankai University): WO 2012/163095 A1(2012).
– reference: 9) M. Mao, Y. Li, Q. Liu, Y. Zhou, X. Zhang, L. Xiong, Y. Li and Z. Li: Bioorg. Med. Chem. Lett. 23, 42–46 (2013).
– reference: 15) N. G. Aher, V. S. Pore, N. N. Mishra, A. Kumar, P. K. Shukla, A. Sharma and M. K. Bhat: Bioorg. Med. Chem. Lett. 19, 759–763 (2009).
– reference: 20) K. van Alem, G. Belder, G. Lodder and H. Zuilhof: J. Org. Chem. 70, 179–190 (2005).
– reference: 1) DuPont Rynaxypyr_insect control Technical Bulletin: http://www2.dupont.com/Production_Agriculture/en_US/assets/downloads/pdfs/ Rynaxypyr_Tech_Bulletin.pdf (Accessd 29 May, 2015)
– reference: 10) J. Wu, B.-A. Song, D.-Y. Hu, M. Yue and S. Yang: Pest Manag. Sci. 68, 801–810 (2012).
– reference: 11) M.-Z. Mao, Y.-X. Li, Y.-Y. Zhou, X.-L. Zhang, Q.-X. Liu, F.-J. Di, H.-B. Song, L.-X. Xiong, Y.-Q. Li and Z.-M. Li: J. Agric. Food Chem. 62, 1536–1542 (2014).
– reference: 16) E. D. Chrysina, É. Bokor, K. Alexacou, M. Charavgi, G. N. Oikonomakos, S. E. Zographos, D. D. Leonidas, N. G. Oikonomakos and L. Somsák: Tetrahedron Asymmetry 20, 733–740 (2009).
– reference: 12) G. D. Annis, B. J. Myers, T. P. Selby, T. M. Stevenson and W. T. Zimmerman (E. I. Du Pont de Nemours and Company): WO 2002/048115 A2 (2002).
– reference: 4) K. A. Hughes, G. P. Lahm, T. P. Selby and T. M. Stevenson (E. I. Du Pont de Nemours and Company): WO 2004/067528 A1 (2004).
– reference: 17) D. Raffa, O. Migliara, B. Maggio, F. Plescia, S. Cascioferro, M. G. Cusimano, G. Tringali, C. Cannizzaro and F. Plescia: Arch. Pharm. 343, 631–638 (2010).
– reference: 5) R. G. Hall, O. Loiseleur, J. Pabba, S. Pal, A. Jeanguenat, A. Edmunds and A. Stoller: WO 2009/010260 A2 (2009).
– reference: 18) J. L. Randall, R. A. Gibbs, G. K. Bosch, M. D. Curtis, L. Sun and N. Nikolaides: US 2004/0167194 A1 (2004).
– reference: 14) G. C. Tron, T. Pirali, R. A. Billington, P. L. Canonico, G. Sorba and A. A. Genazzani: Med. Res. Rev. 28, 278–308 (2008).
– reference: 3) B. L. Finkelstein, G. P. Lahm, S. F. McCann, Y. Song and T. M. Stevenson (E. I. Du Pont de Nemours and Company): WO 2003/016284 A1 (2003).
– reference: 6) B. Li, D. Xiang, B. Chai, J. Yuan, H. Yang, H. Zhang, H. Wu and H. Yu: (Sinochem Corp., Shenyang Research Institute of Chemcal Industry Co. Ltd.): WO 2008/134969 A1(2008).
– ident: 9
  doi: 10.1016/j.bmcl.2012.11.045
– ident: 10
  doi: 10.1002/ps.2329
– ident: 17
  doi: 10.1002/ardp.200900317
– ident: 3
– ident: 18
– ident: 14
  doi: 10.1002/med.20107
– ident: 5
– ident: 4
– ident: 1
– ident: 20
  doi: 10.1021/jo0487956
– ident: 12
– ident: 11
  doi: 10.1021/jf500003d
– ident: 19
  doi: 10.1002/cjoc.201180295
– ident: 13
– ident: 7
  doi: 10.1021/jf102842r
– ident: 2
  doi: 10.1016/j.bmc.2009.01.018
– ident: 6
– ident: 15
  doi: 10.1016/j.bmcl.2008.12.026
– ident: 21
  doi: 10.1002/1521-3773(20020715)41:14<2596::AID-ANIE2596>3.0.CO;2-4
– ident: 8
  doi: 10.1002/cjoc.201200362
– ident: 16
  doi: 10.1016/j.tetasy.2009.03.021
SSID ssj0001737996
ssj0033558
ssib003115495
ssib023157167
ssib023167461
ssib044745361
ssib020475958
ssib008501316
Score 2.0310109
Snippet Based on the commercial insecticide chlorantraniliprole, a series of novel N-pyridylpyrazole derivatives containing 1,2,3-triazole moieties were designed and...
SourceID proquest
crossref
medicalonline
jstage
SourceType Aggregation Database
Enrichment Source
Index Database
Publisher
StartPage 138
SubjectTerms 1,2,3-triazole
biological activity
Insecticides
isosterism
Mythimna separata
N-pyridylpyrazole derivatives
Title Synthesis and biological evaluation of novel N-pyridylpyrazole derivatives containing 1,2,3-triazole moieties
URI https://www.jstage.jst.go.jp/article/jpestics/40/3/40_D15-020/_article/-char/en
http://mol.medicalonline.jp/en/journal/download?GoodsID=cy3jpesc/2015/004003/010&name=0138-0142e
https://www.proquest.com/docview/1755492192
https://www.proquest.com/docview/1768568368
Volume 40
hasFullText 1
inHoldings 1
isFullTextHit
isPrint
ispartofPNX Journal of Pesticide Science, 2015/08/20, Vol.40(3), pp.138-142
link http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwnV3db9MwELe6jgcQQnxNFMZkJF7Q1i2t7SR9gu5LExoTiE0qT5GdOCOoTaquRese-Ev4Y7mznaRbATEe6laufUp85_uwzz8T8lr2NOdBKNoq1RCgCPDhwgSClVCJIJZgcGNlEmRP_KMz_n4gBo3Gz4WspdlUbcdXvz1X8j9chTrgK56SvQVnK6JQAb-Bv1ACh6H8Jx5_nufgvyGkCC5_WzwlM-g1hrdJ1Ci-6-HmSXs8n2TJfAhf8qowB6Ym5m4zBJ7FlHV7WcQm6La9LnxYG6_0MC1HRaanZbrhsiv7EaE64izRpaqo17kLm5ufn199rQ-dHZsUgi-zy2yhaoZ1nzJZXGaVqRhkLmP4OCtr3QpFRyysUFilyjie7jJX5oLNKeswVcueNS41sQVuchLHFtRqxyLAOAvdsXhcS8offClU_mPzzhfb-_gkXa82dOXm_g37V2UlYjwENKKSQgQUIqCwQla7EIR0m2S1v7u_e1iv4QUs6CFcobX8DKHqTYDv3tdtiwPNnZtPdc0NuvMNIgGEeLg_srtzFiVlyT0wPs_pQ_LAcZj2reQ9Ig2dPyb3-ucTB9iin5BRJYMUZJDWMkhrGaRFSo0M0iUZpAsySGsZpJ2t7lYtf7SUv6fk7PDgdO-o7a7waMfC86btUCsF45KqNA46gfTBeeVSe9wXvUQGMkxCHageT3E_O_VhALVImIpVIiV6p5ytkWZe5PoZoTLxPM1E6gspeU_6MvETzVXMmZRJqrwW2SlHNIodvj1eszKM_sTXFnlT9RhbbJe_tH1rmVS1dLO-bsm9iGHhelQN8PgkaKsWeXeNu5FTJBdRPGdIJI5w8kTGrLLIgyfBLAIoONhcX4Cktch6KRB1b_D_EWURIrUWeVX9DUYCd_5krosZtvFD4YfMD5_f4p1fkLv1dF4nzelkpl-CCz5VG24mbJCVDz8OfgFaI-Si
linkProvider EBSCOhost
openUrl ctx_ver=Z39.88-2004&ctx_enc=info%3Aofi%2Fenc%3AUTF-8&rfr_id=info%3Asid%2Fsummon.serialssolutions.com&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.atitle=Synthesis+and+biological+evaluation+of+novel+N-pyridylpyrazole+derivatives+containing+1%2C2%2C3-triazole+moieties&rft.jtitle=Journal+of+Pesticide+Science&rft.au=Mao%2C+Mingzhen&rft.au=Li%2C+Yuxin&rft.au=Liu%2C+Qiaoxia&rft.au=Xiong%2C+Lixia&rft.date=2015-01-01&rft.issn=1348-589X&rft.eissn=1349-0923&rft.volume=40&rft.issue=3&rft.spage=138&rft.epage=142&rft_id=info:doi/10.1584%2Fjpestics.D15-020&rft.externalDBID=n%2Fa&rft.externalDocID=10_1584_jpestics_D15_020
thumbnail_l http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/lc.gif&issn=1348-589X&client=summon
thumbnail_m http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/mc.gif&issn=1348-589X&client=summon
thumbnail_s http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/sc.gif&issn=1348-589X&client=summon