Title:
ENOATE COMPOUND CONTAINING AROMATIC RING, AND PREPARATION THEREFOR AND USE THEREOF
Document Type and Number:
WIPO Patent Application WO/2023/072285
Kind Code:
A1
Abstract:
Disclosed are an enoate compound containing an aromatic ring, and a preparation therefor and the use thereof. The compound of the present invention is simple in terms of structure and easy to synthesize. Synthetic raw materials are derived from natural products, are pollution-free to the environment, and eco-friendly. The compound provided in the present invention has good repelling and killing effects on aphids, has good inhibitory activity on plant pathogenic fungi, can be used as an aphid control agent and a fungicide, and has good application prospects in green control of pests and plant diseases.
Inventors:
YANG XINLING (CN)
PAN SHIXIANG (CN)
YANG ZHAOKAI (CN)
LIU YAN (CN)
QIN YAOGUO (CN)
LING YUN (CN)
SHI ZHUO (CN)
PAN SHIXIANG (CN)
YANG ZHAOKAI (CN)
LIU YAN (CN)
QIN YAOGUO (CN)
LING YUN (CN)
SHI ZHUO (CN)
Application Number:
PCT/CN2022/128593
Publication Date:
May 04, 2023
Filing Date:
October 31, 2022
Export Citation:
Assignee:
UNIV CHINA AGRICULTURAL (CN)
International Classes:
C07C69/533; A01N37/40; A01N43/30; A01N43/38; A01P3/00; A01P7/04; A01P17/00; C07C67/08; C07C69/587; C07C69/86; C07C69/92; C07C205/43; C07D209/08; C07D317/54; C07D317/64
Foreign References:
| CN113831246A | 2021-12-24 | |||
| US20190047937A1 | 2019-02-14 |
Other References:
CONE, W. W.: "Two-Spotted Spider Mite and Hop Aphid Control on Cluster Hops with Acaricides", JOURNAL OF ECONOMIC ENTOMOLOGY, ENTOMOLOGICAL SOCIETY OF AMERICA, LANDHAM, US, vol. 61, no. 6, 21 December 1968 (1968-12-21), US , pages 1685 - 1689, XP009545781, ISSN: 0022-0493, DOI: 10.1093/jee/61.6.1685
DATABASE Registry 4 January 2018 (2018-01-04), ANONYMOUS : "2-Butenoic acid, 3-meth yl-, 2-formylphenyl ester (CA INDEX NA ME)", XP093061635, retrieved from STN Database accession no. 2169453-91-0
LOANA MUSSO; SABRINA DALLAVALLE; LUCIO MERLINI; GANDOLFINA FARINA: "Synthesis and Antifungal Activity of 2‐Hydroxy‐4,5‐methylenedioxyaryl Ketones as Analogues of Kakuol", CHEMISTRY & BIODIVERSITY, HELVETICA CHIMICA ACTA, ZUERICH, CH, vol. 7, no. 4, 15 April 2010 (2010-04-15), CH , pages 887 - 897, XP072353242, ISSN: 1612-1872, DOI: 10.1002/cbdv.200900263
ZHANG KE, ZHANG WEN-ZHEN, TAO XUE-YAN, ZHANG MIN, REN WEI-MIN, LU XIAO-BING: "Carboxylative Cyclization of 2-Butenoates with Carbon Dioxide: Access to Glutaconic Anhydrides", THE JOURNAL OF ORGANIC CHEMISTRY, AMERICAN CHEMICAL SOCIETY, vol. 85, no. 17, 4 September 2020 (2020-09-04), pages 11579 - 11588, XP093061599, ISSN: 0022-3263, DOI: 10.1021/acs.joc.0c01717
LO JULIAN C., KIM DONGYOUNG, PAN CHUNG-MAO, EDWARDS JACOB T., YABE YUKI, GUI JINGHAN, QIN TIAN, GUTIÉRREZ SARA, GIACOBONI JESSICA,: "Fe-Catalyzed C–C Bond Construction from Olefins via Radicals", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, AMERICAN CHEMICAL SOCIETY, vol. 139, no. 6, 15 February 2017 (2017-02-15), pages 2484 - 2503, XP093061600, ISSN: 0002-7863, DOI: 10.1021/jacs.6b13155
BROWN RICHARD C. D., BATAILLE CAROLE J., HUGHES ROBERT M., KENNEY ANNE, LUKER TIM J.: "Permanganate Oxidation of 1,5,9-Trienes: Stereoselective Synthesis of Tetrahydrofuran-Containing Fragments", THE JOURNAL OF ORGANIC CHEMISTRY, AMERICAN CHEMICAL SOCIETY, vol. 67, no. 23, 1 November 2002 (2002-11-01), pages 8079 - 8085, XP093061603, ISSN: 0022-3263, DOI: 10.1021/jo026295b
KIM SANGHEE; KIM EUNKYUNG; SHIN DONG-SUN; KANG HEONJOONG; OH KI-BONG: "Evaluation of Morphogenic Regulatory Activity of Farnesoic acid and Its Derivatives againstCandida albicansDimorphism", BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, ELSEVIER, AMSTERDAM NL, vol. 12, no. 6, 5 June 2017 (2017-06-05), Amsterdam NL , pages 895 - 898, XP085050211, ISSN: 0960-894X, DOI: 10.1016/S0960-894X(02)00038-0
GOUCK H., MCGOVERN T. P., BEROZA MORTON: "Chemicals Tested as Space Repellents Against Yellow-Fever Mosquitoes. I. Esters", JOURNAL OF ECONOMIC ENTOMOLOGY, ENTOMOLOGICAL SOCIETY OF AMERICA, LANDHAM, US, vol. 60, no. 6, 1 December 1967 (1967-12-01), US , pages 1587 - 1590, XP009545828, ISSN: 0022-0493, DOI: 10.1093/jee/60.6.1587
NILLES, G. P. ET AL.,: "“Synthesis of Bioactive Compounds. A Structure-Activity Study of Aryl Terpenes as Juvenile Hormone Mimics”,", JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, vol. 24, no. 4, 1 July 1976 (1976-07-01), XP000993304, ISSN: 0021-8561, DOI: 10.1021/jf60206a015
PALA GIANFRANCO, TIBERIO BRUZZESE, AND BRUNO LUMACHI: "Terpene Compounds as Drugs. V. Terpenyl Derivatives of Salicylic Acid", vol. 11, no. 4, 1 July 1968 (1968-07-01), pages 910 - 911, XP093061608
DATABASE Registry 4 January 2018 (2018-01-04), ANONYMOUS : "2-Butenoic acid, 3-meth yl-, 2-formylphenyl ester (CA INDEX NA ME)", XP093061635, retrieved from STN Database accession no. 2169453-91-0
LOANA MUSSO; SABRINA DALLAVALLE; LUCIO MERLINI; GANDOLFINA FARINA: "Synthesis and Antifungal Activity of 2‐Hydroxy‐4,5‐methylenedioxyaryl Ketones as Analogues of Kakuol", CHEMISTRY & BIODIVERSITY, HELVETICA CHIMICA ACTA, ZUERICH, CH, vol. 7, no. 4, 15 April 2010 (2010-04-15), CH , pages 887 - 897, XP072353242, ISSN: 1612-1872, DOI: 10.1002/cbdv.200900263
ZHANG KE, ZHANG WEN-ZHEN, TAO XUE-YAN, ZHANG MIN, REN WEI-MIN, LU XIAO-BING: "Carboxylative Cyclization of 2-Butenoates with Carbon Dioxide: Access to Glutaconic Anhydrides", THE JOURNAL OF ORGANIC CHEMISTRY, AMERICAN CHEMICAL SOCIETY, vol. 85, no. 17, 4 September 2020 (2020-09-04), pages 11579 - 11588, XP093061599, ISSN: 0022-3263, DOI: 10.1021/acs.joc.0c01717
LO JULIAN C., KIM DONGYOUNG, PAN CHUNG-MAO, EDWARDS JACOB T., YABE YUKI, GUI JINGHAN, QIN TIAN, GUTIÉRREZ SARA, GIACOBONI JESSICA,: "Fe-Catalyzed C–C Bond Construction from Olefins via Radicals", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, AMERICAN CHEMICAL SOCIETY, vol. 139, no. 6, 15 February 2017 (2017-02-15), pages 2484 - 2503, XP093061600, ISSN: 0002-7863, DOI: 10.1021/jacs.6b13155
BROWN RICHARD C. D., BATAILLE CAROLE J., HUGHES ROBERT M., KENNEY ANNE, LUKER TIM J.: "Permanganate Oxidation of 1,5,9-Trienes: Stereoselective Synthesis of Tetrahydrofuran-Containing Fragments", THE JOURNAL OF ORGANIC CHEMISTRY, AMERICAN CHEMICAL SOCIETY, vol. 67, no. 23, 1 November 2002 (2002-11-01), pages 8079 - 8085, XP093061603, ISSN: 0022-3263, DOI: 10.1021/jo026295b
KIM SANGHEE; KIM EUNKYUNG; SHIN DONG-SUN; KANG HEONJOONG; OH KI-BONG: "Evaluation of Morphogenic Regulatory Activity of Farnesoic acid and Its Derivatives againstCandida albicansDimorphism", BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, ELSEVIER, AMSTERDAM NL, vol. 12, no. 6, 5 June 2017 (2017-06-05), Amsterdam NL , pages 895 - 898, XP085050211, ISSN: 0960-894X, DOI: 10.1016/S0960-894X(02)00038-0
GOUCK H., MCGOVERN T. P., BEROZA MORTON: "Chemicals Tested as Space Repellents Against Yellow-Fever Mosquitoes. I. Esters", JOURNAL OF ECONOMIC ENTOMOLOGY, ENTOMOLOGICAL SOCIETY OF AMERICA, LANDHAM, US, vol. 60, no. 6, 1 December 1967 (1967-12-01), US , pages 1587 - 1590, XP009545828, ISSN: 0022-0493, DOI: 10.1093/jee/60.6.1587
NILLES, G. P. ET AL.,: "“Synthesis of Bioactive Compounds. A Structure-Activity Study of Aryl Terpenes as Juvenile Hormone Mimics”,", JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, vol. 24, no. 4, 1 July 1976 (1976-07-01), XP000993304, ISSN: 0021-8561, DOI: 10.1021/jf60206a015
PALA GIANFRANCO, TIBERIO BRUZZESE, AND BRUNO LUMACHI: "Terpene Compounds as Drugs. V. Terpenyl Derivatives of Salicylic Acid", vol. 11, no. 4, 1 July 1968 (1968-07-01), pages 910 - 911, XP093061608
Attorney, Agent or Firm:
JEEKAI&PARTNERS (CN)
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