CN113004240A - Benzopyran compound and application thereof in pesticides - Google Patents
Benzopyran compound and application thereof in pesticides Download PDFInfo
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- CN113004240A CN113004240A CN202110263879.9A CN202110263879A CN113004240A CN 113004240 A CN113004240 A CN 113004240A CN 202110263879 A CN202110263879 A CN 202110263879A CN 113004240 A CN113004240 A CN 113004240A
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- 239000000575 pesticide Substances 0.000 title claims abstract description 22
- -1 Benzopyran compound Chemical class 0.000 title abstract description 18
- 150000001875 compounds Chemical class 0.000 claims abstract description 86
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 17
- 241000607479 Yersinia pestis Species 0.000 claims abstract description 14
- 230000000844 anti-bacterial effect Effects 0.000 claims abstract description 13
- 150000001562 benzopyrans Chemical class 0.000 claims abstract description 13
- 238000002360 preparation method Methods 0.000 claims abstract description 12
- 239000003899 bactericide agent Substances 0.000 claims abstract description 10
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 9
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims abstract description 9
- 239000002917 insecticide Substances 0.000 claims abstract description 9
- 125000005843 halogen group Chemical group 0.000 claims abstract description 8
- 230000001580 bacterial effect Effects 0.000 claims description 12
- 229910052801 chlorine Inorganic materials 0.000 claims description 11
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 11
- 241000894006 Bacteria Species 0.000 claims description 10
- 239000000417 fungicide Substances 0.000 claims description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
- KYNSBQPICQTCGU-UHFFFAOYSA-N Benzopyrane Chemical compound C1=CC=C2C=CCOC2=C1 KYNSBQPICQTCGU-UHFFFAOYSA-N 0.000 claims description 7
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 6
- 229910052731 fluorine Inorganic materials 0.000 claims description 6
- 241001477931 Mythimna unipuncta Species 0.000 claims description 5
- 241000344246 Tetranychus cinnabarinus Species 0.000 claims description 5
- 125000001153 fluoro group Chemical group F* 0.000 claims description 5
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 claims description 5
- 244000298697 Actinidia deliciosa Species 0.000 claims description 4
- 235000009436 Actinidia deliciosa Nutrition 0.000 claims description 4
- 241001425390 Aphis fabae Species 0.000 claims description 4
- 240000007124 Brassica oleracea Species 0.000 claims description 4
- 235000003899 Brassica oleracea var acephala Nutrition 0.000 claims description 4
- 235000011301 Brassica oleracea var capitata Nutrition 0.000 claims description 4
- 235000001169 Brassica oleracea var oleracea Nutrition 0.000 claims description 4
- 244000017020 Ipomoea batatas Species 0.000 claims description 4
- 235000002678 Ipomoea batatas Nutrition 0.000 claims description 4
- 244000061176 Nicotiana tabacum Species 0.000 claims description 4
- 235000002637 Nicotiana tabacum Nutrition 0.000 claims description 4
- 240000007594 Oryza sativa Species 0.000 claims description 4
- 235000007164 Oryza sativa Nutrition 0.000 claims description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
- 235000009566 rice Nutrition 0.000 claims description 4
- 208000025865 Ulcer Diseases 0.000 claims 1
- 231100000397 ulcer Toxicity 0.000 claims 1
- 238000000034 method Methods 0.000 abstract description 7
- 230000000607 poisoning effect Effects 0.000 abstract description 5
- 230000000694 effects Effects 0.000 abstract description 4
- 230000015572 biosynthetic process Effects 0.000 abstract description 3
- 230000005764 inhibitory process Effects 0.000 abstract description 3
- 238000003786 synthesis reaction Methods 0.000 abstract description 3
- 230000001717 pathogenic effect Effects 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 39
- 238000001228 spectrum Methods 0.000 description 32
- 238000006243 chemical reaction Methods 0.000 description 26
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 24
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 24
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 18
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- 229910052739 hydrogen Inorganic materials 0.000 description 18
- 239000001257 hydrogen Substances 0.000 description 18
- 239000011541 reaction mixture Substances 0.000 description 18
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
- 239000007787 solid Substances 0.000 description 13
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- 229910052799 carbon Inorganic materials 0.000 description 12
- 239000012043 crude product Substances 0.000 description 12
- 239000012153 distilled water Substances 0.000 description 12
- 239000005457 ice water Substances 0.000 description 12
- 238000001819 mass spectrum Methods 0.000 description 12
- 230000007935 neutral effect Effects 0.000 description 12
- 238000003756 stirring Methods 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 239000007864 aqueous solution Substances 0.000 description 9
- 239000000523 sample Substances 0.000 description 9
- 238000012360 testing method Methods 0.000 description 9
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
- 240000006677 Vicia faba Species 0.000 description 7
- 235000010749 Vicia faba Nutrition 0.000 description 7
- 235000002098 Vicia faba var. major Nutrition 0.000 description 7
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 6
- 238000005160 1H NMR spectroscopy Methods 0.000 description 6
- DQFBYFPFKXHELB-UHFFFAOYSA-N Chalcone Natural products C=1C=CC=CC=1C(=O)C=CC1=CC=CC=C1 DQFBYFPFKXHELB-UHFFFAOYSA-N 0.000 description 6
- 244000046052 Phaseolus vulgaris Species 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- 235000005513 chalcones Nutrition 0.000 description 6
- CUONGYYJJVDODC-UHFFFAOYSA-N malononitrile Chemical compound N#CCC#N CUONGYYJJVDODC-UHFFFAOYSA-N 0.000 description 6
- 239000011259 mixed solution Substances 0.000 description 6
- 239000000741 silica gel Substances 0.000 description 6
- 229910002027 silica gel Inorganic materials 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- DQFBYFPFKXHELB-VAWYXSNFSA-N trans-chalcone Chemical compound C=1C=CC=CC=1C(=O)\C=C\C1=CC=CC=C1 DQFBYFPFKXHELB-VAWYXSNFSA-N 0.000 description 6
- 244000000005 bacterial plant pathogen Species 0.000 description 5
- 238000007865 diluting Methods 0.000 description 5
- 238000002474 experimental method Methods 0.000 description 5
- 230000000749 insecticidal effect Effects 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- FABVMBDCVAJXMB-UHFFFAOYSA-N 3,5-dichloro-2-hydroxybenzaldehyde Chemical compound OC1=C(Cl)C=C(Cl)C=C1C=O FABVMBDCVAJXMB-UHFFFAOYSA-N 0.000 description 4
- 241000238631 Hexapoda Species 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- 230000000855 fungicidal effect Effects 0.000 description 4
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 4
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 4
- 229920000053 polysorbate 80 Polymers 0.000 description 4
- 238000011160 research Methods 0.000 description 4
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- 238000005286 illumination Methods 0.000 description 3
- 230000002401 inhibitory effect Effects 0.000 description 3
- 231100000053 low toxicity Toxicity 0.000 description 3
- 239000002609 medium Substances 0.000 description 3
- 239000013642 negative control Substances 0.000 description 3
- BUZYGTVTZYSBCU-UHFFFAOYSA-N 1-(4-chlorophenyl)ethanone Chemical compound CC(=O)C1=CC=C(Cl)C=C1 BUZYGTVTZYSBCU-UHFFFAOYSA-N 0.000 description 2
- ZDPAWHACYDRYIW-UHFFFAOYSA-N 1-(4-fluorophenyl)ethanone Chemical compound CC(=O)C1=CC=C(F)C=C1 ZDPAWHACYDRYIW-UHFFFAOYSA-N 0.000 description 2
- GNKZMNRKLCTJAY-UHFFFAOYSA-N 4'-Methylacetophenone Chemical compound CC(=O)C1=CC=C(C)C=C1 GNKZMNRKLCTJAY-UHFFFAOYSA-N 0.000 description 2
- NTPLXRHDUXRPNE-UHFFFAOYSA-N 4-methoxyacetophenone Chemical compound COC1=CC=C(C(C)=O)C=C1 NTPLXRHDUXRPNE-UHFFFAOYSA-N 0.000 description 2
- FUGKCSRLAQKUHG-UHFFFAOYSA-N 5-chloro-2-hydroxybenzaldehyde Chemical compound OC1=CC=C(Cl)C=C1C=O FUGKCSRLAQKUHG-UHFFFAOYSA-N 0.000 description 2
- 241001124076 Aphididae Species 0.000 description 2
- 239000001888 Peptone Substances 0.000 description 2
- 108010080698 Peptones Proteins 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 230000003385 bacteriostatic effect Effects 0.000 description 2
- 235000015278 beef Nutrition 0.000 description 2
- 238000009395 breeding Methods 0.000 description 2
- 230000001488 breeding effect Effects 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 230000015556 catabolic process Effects 0.000 description 2
- 238000012258 culturing Methods 0.000 description 2
- 238000006731 degradation reaction Methods 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 235000019319 peptone Nutrition 0.000 description 2
- 238000012827 research and development Methods 0.000 description 2
- 238000002791 soaking Methods 0.000 description 2
- 241000238876 Acari Species 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 244000052616 bacterial pathogen Species 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 239000012470 diluted sample Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 239000001963 growth medium Substances 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000002611 lead compounds Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000000691 measurement method Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 230000001766 physiological effect Effects 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000012488 sample solution Substances 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000010267 two-fold dilution method Methods 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/58—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
- A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
- A01N43/14—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom six-membered rings
- A01N43/16—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom six-membered rings with oxygen as the ring hetero atom
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
The invention relates to benzopyran compounds and application thereof in pesticides, belonging to the technical field of pesticides. The invention aims to provide a benzopyran compound which can be used as an insecticide and a bactericide. The structural general formula of the benzopyran compound is shown in formula I, wherein R is1Is a hydrogen atom, a halogen atom, a C1-C4 alkyl group or a C1-C4 alkoxy group; r2Is hydrogen atom, halogen atom, C1-C4 alkyl or C1-C4 alkoxy. The compound has simple synthesis process, good poisoning effect on pests and good inhibition effect on plant pathogenic bacteriaThe preparation method lays a good foundation for the creation of new pesticides.
Description
Technical Field
The invention relates to benzopyran compounds and application thereof in pesticides, belonging to the technical field of pesticides.
Background
As a traditional big agricultural country in China, crops are always an important support for maintaining the lives of people in China. Similarly, agricultural chemicals produced by crops are a link of great concern. Pesticides are mainly divided into three categories, i.e. herbicides, insecticides and bactericides, and with the wide application of insecticides and bactericides, the resistance of pests, germs and the like to the pesticides is continuously increased, so that more insecticides and bactericides need to be researched. In addition, with the increasing emphasis on food safety, the pursuit of green and organic properties is the current trend, and the use of pesticides is also influenced to a certain extent, and it is necessary to research novel pesticides having the characteristics of high efficiency, low toxicity, safety to non-target organisms, easy degradation in the environment, difficult generation of resistance by pests, and the like.
Benzo-heterocycles are important in the research and development of pesticides and medicines. Benzopyrans and derivatives thereof are a class of compounds with a wide range of physiological and pharmacological activities and are widely present in plants in nature. For many years, a great deal of research work has been carried out in this field, and particularly the synthesis of benzopyran derivatives and their research on pharmacology has been abnormally active. Many high-efficiency and low-toxicity medicinal compounds are synthesized by various methods, but reports of applying benzopyran and derivatives thereof as active compounds to pesticide research are few.
Meanwhile, benzopyran-containing compounds are generally characterized by high efficiency, low toxicity, safety to non-target organisms, easy degradation in the environment, difficult generation of resistance by pests, and the like, and compounds with novel structures and excellent performance are continuously available. Therefore, in the research and development process of pesticides, benzopyran-containing compounds will receive more extensive attention and become hot spots and frontiers for creating new pesticides.
To date, there has been no report of the use of benzopyran compounds as pesticides and fungicides.
Disclosure of Invention
In view of the above defects, the technical problem to be solved by the present invention is to provide a benzopyran compound which can be used as an insecticide and a bactericide.
The structural general formula of the benzopyran compound is shown as formula I:
wherein R is1Is a hydrogen atom, a halogen atom, a C1-C4 alkyl group or a C1-C4 alkoxy group; r2Is hydrogen atom, halogen atom, C1-C4 alkyl or C1-C4 alkoxy.
In some embodiments of the invention, R1Is hydrogen atom, chlorine atom, bromine atom, methyl or methoxy; r2Is hydrogen atom, fluorine atom, chlorine atom, bromine atom, methyl or methoxyl.
In some embodiments of the invention, R1Is a hydrogen atom or a chlorine atom; r2Is a fluorine atomChlorine atom, methyl group or methoxy group.
In some embodiments of the invention, the compound has the structural formula:
the invention also provides application of the benzopyran compound in preparing agricultural fungicides.
The benzopyran compound has good bactericidal activity and can be used for preparing agricultural bactericides.
In some embodiments, the bacteria controlled by the agricultural fungicide are bacteria.
In some embodiments, the bacteria controlled by the agricultural fungicide are rice bacterial blight, cabbage soft rot, sweet potato blast, kiwifruit canker or tobacco bacterial wilt.
The invention also provides application of the benzopyran compound in preparing agricultural pesticides.
The benzopyran compound has good insecticidal activity and can be used for preparing agricultural insecticides.
In some embodiments, the pest controlled by the agricultural pesticide is armyworm, tetranychus cinnabarinus or aphis fabae.
Compared with the prior art, the invention has the following beneficial effects:
the benzopyran compounds are synthesized, active compounds or active lead compounds with novel structures and excellent activity are found, the compound is simple in synthesis process, has a good poisoning effect on pests, has a good inhibition effect on plant pathogenic bacteria, and lays a good foundation for creating new pesticides.
Drawings
FIG. 1 is a nuclear magnetic hydrogen spectrum of the compound of example 1.
FIG. 2 is a partial enlarged view of the nuclear magnetic hydrogen spectrum of the compound of example 1.
FIG. 3 is a nuclear magnetic carbon spectrum of the compound of example 1.
FIG. 4 is a high resolution mass spectrum of the compound of example 1.
FIG. 5 is a nuclear magnetic hydrogen spectrum of the compound of example 2.
FIG. 6 is a partial enlarged view of the nuclear magnetic hydrogen spectrum of the compound of example 2.
FIG. 7 is a nuclear magnetic carbon spectrum of the compound of example 2.
FIG. 8 is a high resolution mass spectrum of the compound of example 2.
FIG. 9 is a nuclear magnetic hydrogen spectrum of the compound of example 3.
FIG. 10 is a partial enlarged view of the nuclear magnetic hydrogen spectrum of the compound of example 3.
FIG. 11 is a nuclear magnetic carbon spectrum of the compound of example 3.
FIG. 12 is a high resolution mass spectrum of the compound of example 3.
FIG. 13 is a nuclear magnetic hydrogen spectrum of the compound of example 4.
FIG. 14 is a partial enlarged view of a nuclear magnetic hydrogen spectrum of the compound of example 4.
FIG. 15 is a nuclear magnetic carbon spectrum of the compound of example 4.
FIG. 16 is a high resolution mass spectrum of the compound of example 4.
FIG. 17 is a nuclear magnetic hydrogen spectrum of the compound of example 5.
FIG. 18 is a partial enlarged view of a nuclear magnetic hydrogen spectrum of the compound of example 5.
FIG. 19 is a nuclear magnetic carbon spectrum of the compound of example 5.
FIG. 20 is a high resolution mass spectrum of the compound of example 5.
FIG. 21 is a nuclear magnetic hydrogen spectrum of the compound of example 6.
FIG. 22 is a close-up view of the nuclear magnetic hydrogen spectrum of the compound of example 6.
FIG. 23 is a nuclear magnetic carbon spectrum of the compound of example 6.
FIG. 24 is a high resolution mass spectrum of the compound of example 6.
Detailed Description
The benzopyran compound has a structural general formula shown in formula I:
wherein R is1Is a hydrogen atom, a halogen atom, a C1-C4 alkyl group or a C1-C4 alkoxy group; r2Is hydrogen atom, halogen atom, C1-C4 alkyl or C1-C4 alkoxy.
In the present invention, the "C1-C4 alkyl group" means a straight-chain or branched alkyl group having 1 to 4 carbon atoms, for example, methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, etc.
"C1-C4 alkoxy" refers to a straight or branched chain alkoxy group having 1 to 4 carbon atoms, such as methoxy, ethoxy, propoxy, isopropoxy, n-butoxy, sec-butoxy, tert-butoxy, and the like.
In some embodiments of the invention, R1Is hydrogen atom, chlorine atom, bromine atom, methyl or methoxy; r2Is hydrogen atom, fluorine atom, chlorine atom, bromine atom, methyl or methoxyl.
In some embodiments of the invention, R1Is a hydrogen atom or a chlorine atom; r2Is fluorine atom, chlorine atom, methyl or methoxyl.
In some embodiments of the invention, the benzopyran-based compound has the structural formula:
the benzopyran compound can be prepared by adopting the conventional method in the field.
In some embodiments of the invention, benzopyrans are synthesized using the following route:
the invention also provides application of the benzopyran compound in preparing agricultural fungicides.
The benzopyran compound has good bactericidal activity and can be used for preparing agricultural bactericides.
In some embodiments, the bacteria controlled by the agricultural fungicide are bacteria.
In some embodiments, the bacteria controlled by the agricultural fungicide are rice bacterial blight, cabbage soft rot, sweet potato blast, kiwifruit canker or tobacco bacterial wilt.
The invention also provides application of the benzopyran compound in preparing agricultural pesticides.
The benzopyran compound has good insecticidal activity and can be used for preparing agricultural insecticides.
In some embodiments, the pest controlled by the agricultural pesticide is armyworm, tetranychus cinnabarinus or aphis fabae.
The following examples are provided to further illustrate the embodiments of the present invention and are not intended to limit the scope of the present invention.
The synthetic route adopted in the examples is:
example 1
adding 10mmol of 4-fluoroacetophenone into 40mL of 10% NaOH aqueous solution, stirring for 30 minutes at 40-45 ℃, adding 10mmol of 5-chlorosalicylaldehyde into the reaction mixture, continuing to react for 10-15 hours, and checking whether the reaction is finished by using a thin-layer silica gel plate (TLC). After completion of the reaction, the reaction mixture was poured into ice water, the pH of the solution was adjusted to neutral with 10% hydrochloric acid solution, and a solid was precipitated, filtered, and washed with distilled water. The obtained crude product is recrystallized by absolute ethyl alcohol to obtain a chalcone intermediate.
10mmol of the home-made intermediate was dissolved in 20mL of N, N-Dimethylformamide (DMF) and 10mmol of K was added2CO3Then, a mixed solution of 10mmol of malononitrile and 20mL of DMF was slowly dropped into the above solution through a constant pressure dropping funnel. Reacting for 4-6 h under the condition of stirring at 40-45 ℃, and checking whether the reaction is finished by TLC. After completion of the reaction, the reaction mixture was poured into ice water, the pH of the solution was adjusted to neutral with 10% hydrochloric acid solution, and a solid was precipitated, filtered, and washed with distilled water. Recrystallizing the obtained crude product by using absolute ethyl alcohol to obtain a target compound, wherein the physical and chemical properties of the target compound are as follows:
brown crystals; the yield is 87%;1H NMR(400MHz,DMSO-d6)δ(ppm):8.02(2H,dd,J=8.8,6.0Hz),7.41(1H,d,J=2.4Hz),7.32(2H,t,J=8.4Hz),7.27(1H,dd,J=8.8,2.4Hz),7.01(1H,d,J=8.8Hz),6.91(2H,s),4.11(1H,t,J=5.2Hz),3.44(2H,dd,J=5.2,2.0Hz);13C NMR(100MHz,DMSO-d6)δ(ppm):196.80,165.52(d,J=250.0Hz),161.79,148.71,133.89(d,J=3.0Hz),131.53(d,J=9.0Hz),128.41,128.29,128.21,126.43,120.70,118.13,116.10(d,J=22.0Hz),54.20,46.63,31.36;HRMS(ESI)m/z:Calcd for C18H12N2O2FCl[M+Na]+:365.0464,Found:365.0456.
the nuclear magnetic hydrogen spectrum of the compound is shown in figure 1, and the overlapped or dense part in figure 1 is shown in figure 2 in detail. The nuclear magnetic carbon spectrum of the compound is shown in fig. 3, and a partial enlarged view of overlapped or dense parts in the nuclear magnetic carbon spectrum is also shown in fig. 3. The high resolution mass spectrum of this compound is shown in FIG. 4.
Example 2
adding 10mmol of 4-fluoroacetophenone into 40mL of 10% NaOH aqueous solution, stirring for 30 minutes at 40-45 ℃, adding 10mmol of 3, 5-dichlorosalicylaldehyde into the reaction mixture, continuing to react for 10-15 hours, and checking whether the reaction is finished by using a thin-layer silica gel plate (TLC). After completion of the reaction, the reaction mixture was poured into ice water, the pH of the solution was adjusted to neutral with 10% hydrochloric acid solution, and a solid was precipitated, filtered, and washed with distilled water. The obtained crude product is recrystallized by absolute ethyl alcohol to obtain a chalcone intermediate.
10mmol of the home-made intermediate was dissolved in 20mL DMF and 10mmol K was added2CO3Then, a mixed solution of 10mmol of malononitrile and 20mL of DMF was slowly dropped into the above solution through a constant pressure dropping funnel. Reacting for 4-6 h under the condition of stirring at 40-45 ℃, and checking whether the reaction is finished by TLC. After completion of the reaction, the reaction mixture was poured into ice water, the pH of the solution was adjusted to neutral with 10% hydrochloric acid solution, and a solid was precipitated, filtered, and washed with distilled water. Recrystallizing the obtained crude product by using absolute ethyl alcohol to obtain a target compound, wherein the physical and chemical properties of the target compound are as follows:
a yellow powder; the yield is 85 percent;1H NMR(400MHz,DMSO-d6)δ(ppm):8.01(2H,dd,J=8.8,5.6Hz),7.75(1H,d,J=2.0Hz),7.56(1H,d,J=2.4Hz),7.32(2H,t,J=8.8Hz),7.05(2H,s),4.12(1H,t,J=5.2Hz),3.52(1H,dd,J=17.2,5.6Hz),3.43(1H,dd,J=17.2,4.8Hz);13C NMR(100MHz,DMSO-d6)δ(ppm):196.68,165.57(d,J=251.0Hz),161.33,144.92,133.80(d,J=3.0Hz),131.53(d,J=9.0Hz),128.36,128.28,128.07,127.20,121.47,120.28,116.11(d,J=22.0Hz),54.46,46.22,31.71;HRMS(ESI)m/z:Calcd for C18H11N2O2FCl2[M+Na]+:399.0074,Found:399.0070.
the nuclear magnetic hydrogen spectrum of the compound is shown in figure 5, and the overlapped or dense part in figure 5 is shown in figure 6 in detail. The NMR spectrum of the compound is shown in FIG. 7, and a close-up view of the overlapped or dense part of the NMR spectrum is also shown in FIG. 7. The high resolution mass spectrum of this compound is shown in FIG. 8.
Example 3
adding 10mmol of 4-chloroacetophenone into 40mL of 10% NaOH aqueous solution, stirring for 30 minutes at 40-45 ℃, adding 10mmol of 5-chlorosalicylaldehyde into the reaction mixture, continuing to react for 10-15 hours, and checking whether the reaction is finished by using a thin-layer silica gel plate (TLC). After completion of the reaction, the reaction mixture was poured into ice water, the pH of the solution was adjusted to neutral with 10% hydrochloric acid solution, and a solid was precipitated, filtered, and washed with distilled water. The obtained crude product is recrystallized by absolute ethyl alcohol to obtain a chalcone intermediate.
10mmol of the home-made intermediate was dissolved in 20mL DMF and 10mmol K was added2CO3Then, a mixed solution of 10mmol of malononitrile and 20mL of DMF was slowly dropped into the above solution through a constant pressure dropping funnel. Reacting for 4-6 h under the condition of stirring at 40-45 ℃, and checking whether the reaction is finished by TLC. After completion of the reaction, the reaction mixture was poured into ice water, the pH of the solution was adjusted to neutral with 10% hydrochloric acid solution, and a solid was precipitated, filtered, and washed with distilled water. Recrystallizing the obtained crude product by using absolute ethyl alcohol to obtain a target compound, wherein the physical and chemical properties of the target compound are as follows:
a light yellow powder; the yield is 88%;1H NMR(400MHz,DMSO-d6)δ(ppm):7.95(2H,d,J=8.8Hz),7.57(2H,d,J=8.8Hz),7.42(1H,d,J=2.4Hz),7.27(1H,dd,J=8.8,2.4Hz),7.01(1H,d,J=8.8Hz),6.94(2H,s),4.11(1H,t,J=5.6Hz),3.50-3.40(2H,m);13C NMR(100MHz,DMSO-d6)δ(ppm):196.79,154.91,143.96,137.29,134.45,129.05,128.33,127.66,127.52,126.13,122.98,122.90,114.93,54.64,48.13,36.75;HRMS(ESI)m/z:Calcd for C18H12N2O2Cl2[M+H]+:359.0354,Found:359.0356.
the nuclear magnetic hydrogen spectrum of the compound is shown in figure 9, and the overlapped or dense part in figure 9 is shown in detail in figure 10. The nuclear magnetic carbon spectrum of the compound is shown in fig. 11, and a partial enlarged view of overlapped or dense parts in the nuclear magnetic carbon spectrum is also shown in fig. 11. The high resolution mass spectrum of the compound is shown in figure 12.
Example 4
adding 10mmol of 4-chloroacetophenone into 40mL of 10% NaOH aqueous solution, stirring for 30 minutes at 40-45 ℃, adding 10mmol of 3, 5-dichlorosalicylaldehyde into the reaction mixture, continuing to react for 10-15 hours, and checking whether the reaction is finished by using a thin-layer silica gel plate (TLC). After completion of the reaction, the reaction mixture was poured into ice water, the pH of the solution was adjusted to neutral with 10% hydrochloric acid solution, and a solid was precipitated, filtered, and washed with distilled water. The obtained crude product is recrystallized by absolute ethyl alcohol to obtain a chalcone intermediate.
10mmol of the home-made intermediate was dissolved in 20mL DMF and 10mmol K was added2CO3Then, a mixed solution of 10mmol of malononitrile and 20mL of DMF was slowly dropped into the above solution through a constant pressure dropping funnel. Reacting for 4-6 h under the condition of stirring at 40-45 ℃, and checking whether the reaction is finished by TLC. After completion of the reaction, the reaction mixture was poured into ice water, the pH of the solution was adjusted to neutral with 10% hydrochloric acid solution, and a solid was precipitated, filtered, and washed with distilled water. Recrystallizing the obtained crude product by using absolute ethyl alcohol to obtain a target compound, wherein the physical and chemical properties of the target compound are as follows:
a yellow powder; the yield is 89%;1H NMR(400MHz,DMSO-d6)δ(ppm):8.04-8.00(2H,m),7.55(1H,s),7.43(1H,s),7.33(2H,t,J=8.4Hz),7.06(2H,s),4.14(1H,s),3.52(1H,dd,J=17.6,5.2Hz),3.46(1H,dd,J=17.6,4.8Hz);13C NMR(100MHz,DMSO-d6)δ(ppm):196.70,161.44,133.68,131.59,131.49,130.65,129.74,128.39,120.30,116.45,116.23,116.01,110.80,56.49,54.53,31.76;HRMS(ESI)m/z:Calcd for C18H11N2O2Cl3[M+H]+:392.9964,Found:392.9920.
the nuclear magnetic hydrogen spectrum of the compound is shown in FIG. 13, and the overlapped or dense part in FIG. 13 is shown in detail in FIG. 14. The nmr spectrum of the compound is shown in fig. 15, and a close-up view of the overlapping or dense part of the nmr spectrum is shown in fig. 15. The high resolution mass spectrum of this compound is shown in FIG. 16.
Example 5
adding 10mmol of 4-methylacetophenone into 40mL of 10% NaOH aqueous solution, stirring for 30 minutes at 40-45 ℃, adding 10mmol of 3, 5-dichlorosalicylaldehyde into the reaction mixture, continuing the reaction for 10-15 hours, and checking whether the reaction is finished by using a thin-layer silica gel plate (TLC). After completion of the reaction, the reaction mixture was poured into ice water, the pH of the solution was adjusted to neutral with 10% hydrochloric acid solution, and a solid was precipitated, filtered, and washed with distilled water. The obtained crude product is recrystallized by absolute ethyl alcohol to obtain a chalcone intermediate.
10mmol of the home-made intermediate was dissolved in 20mL DMF and 10mmol K was added2CO3Then, a mixed solution of 10mmol of malononitrile and 20mL of DMF was slowly dropped into the above solution through a constant pressure dropping funnel. Reacting for 4-6 h under the condition of stirring at 40-45 ℃, and checking whether the reaction is finished by TLC. After completion of the reaction, the reaction mixture was poured into ice water, the pH of the solution was adjusted to neutral with 10% hydrochloric acid solution, and a solid was precipitated, filtered, and washed with distilled water. Recrystallizing the obtained crude product by using absolute ethyl alcohol to obtain a target compound, wherein the physical and chemical properties of the target compound are as follows:
a white powder; the yield is 87%;1H NMR(400MHz,DMSO-d6)δ(ppm):7.83(2H,d,J=8.4Hz)7.55(1H,d,J=2.4Hz),7.41(1H,d,J=2.4Hz),7.31(2H,d,J=8.0Hz),7.04(2H,s),4.12(1H,t,J=5.2Hz),3.48(1H,dd,J=17.6,5.6Hz),3.42(1H,dd,J=17.2,5.2Hz),2.37(3H,s);13C NMR(100MHz,DMSO-d6)δ(ppm):197.53,161.30,144.92,144.20,134.62,129.67,128.59,128.33,128.24,128.22,127.17,121.46,120.29,54.56,46.11,31.72,21.60;HRMS(ESI)m/z:Calcd for C19H14N2O2Cl2[M+Na]+:395.0325,Found:395.0318.
the nuclear magnetic hydrogen spectrum of the compound is shown in FIG. 17, and the overlapped or dense part in FIG. 17 is shown in detail in FIG. 18. The NMR spectrum of the compound is shown in FIG. 19, and a partial enlarged view of the overlapped or dense part of the NMR spectrum is also shown in FIG. 19. The high resolution mass spectrum of the compound is shown in figure 20.
Example 6
adding 10mmol of 4-methoxyacetophenone into 40mL of 10% NaOH aqueous solution, stirring for 30 minutes at 40-45 ℃, adding 10mmol of 3, 5-dichlorosalicylaldehyde into the reaction mixture, continuing the reaction for 10-15 hours, and checking whether the reaction is finished by using a thin-layer silica gel plate (TLC). After completion of the reaction, the reaction mixture was poured into ice water, the pH of the solution was adjusted to neutral with 10% hydrochloric acid solution, and a solid was precipitated, filtered, and washed with distilled water. The obtained crude product is recrystallized by absolute ethyl alcohol to obtain a chalcone intermediate.
10mmol of the home-made intermediate was dissolved in 20mL DMF and 10mmol K was added2CO3Then, a mixed solution of 10mmol of malononitrile and 20mL of DMF was slowly dropped into the above solution through a constant pressure dropping funnel. Reacting for 4-6 h under the condition of stirring at 40-45 ℃, and checking whether the reaction is finished by TLC. After completion of the reaction, the reaction mixture was poured into ice water, the pH of the solution was adjusted to neutral with 10% hydrochloric acid solution, and a solid was precipitated, filtered, and washed with distilled water. Recrystallizing the obtained crude product by using absolute ethyl alcohol to obtain a target compound, wherein the physical and chemical properties of the target compound are as follows:
a yellow powder; the yield is 92 percent;1H NMR(400MHz,DMSO-d6)δ(ppm):7.91(2H,d,J=8.8Hz),7.54(1H,d,J=2.4Hz),7.40(1H,d,J=2.4Hz),7.05(2H,s),7.01(2H,d,J=8.8Hz),4.12(1H,t,J=5.2Hz),3.84(3H,s),3.47-3.37(2H,m);13C NMR(100MHz,DMSO-d6)δ(ppm):196.42,163.66,161.75,148.68,130.84,130.12,128.36,128.24,128.17,126.64,120.77,118.13,114.30,56.00,54.32,46.31,31.39;HRMS(ESI)m/z:Calcd for C19H14N2O3Cl2[M+Na]+:377.0663,Found:377.0650.
the nuclear magnetic hydrogen spectrum of the compound is shown in FIG. 21, and the overlapped or dense part in FIG. 21 is shown in detail in FIG. 22. The nuclear magnetic carbon spectrum of the compound is shown in fig. 23, and a partial enlarged view of overlapped or dense parts of the nuclear magnetic carbon spectrum is also shown in fig. 23. The high resolution mass spectrum of this compound is shown in FIG. 24.
Test example 1 measurement of insecticidal Activity of the Compound of the present invention
(1) Test pest
Armyworm larvae of 3 rd age, tetranychus cinnabarinus adults, and Aphis fabae of 3 rd age, all of which are sensitive strains bred indoors all year round.
(2) Method for measuring armyworm
Dissolving a sample to be detected in dimethyl sulfoxide, diluting the sample to a certain concentration by using 0.1% Tween-80 aqueous solution, and taking a corresponding solution without the sample to be detected as a negative control. Cutting corn leaves into 2 multiplied by 4cm small sections, soaking the small sections in a solution to be detected for 5s, taking the small sections out, draining the small sections, putting the small sections into a culture dish (6cm) with filter paper paved at the bottom, inoculating 15 larvae of 3 years old, further placing the small sections in a laboratory with the temperature of 22-24 ℃, the relative humidity of 60% and the illumination time of 14:10h for continuous breeding, recording the death condition after 24h, repeating each experiment for 3 times, and calculating and correcting the death rate by using the following formula:
(3) method for determining tetranychus cinnabarinus
Dissolving a sample to be detected in dimethyl sulfoxide, diluting the sample to a certain concentration by using 0.1% Tween-80 aqueous solution, and taking a corresponding solution without the sample to be detected as a negative control. Collecting kidney bean leaves with high insect population density, carefully selecting to enable healthy adult mites (30-50 heads) to remain on leaf surfaces, soaking the kidney bean leaves with the insects into a solution to be detected for 5s, taking the kidney bean leaves away, draining the kidney bean leaves, putting the kidney bean leaves into a culture dish (6cm) with filter paper paved at the bottom, placing the kidney bean leaves in a laboratory with the temperature of 22-24 ℃, the relative humidity of 60% and the illumination time of 14:10h for continuous breeding, recording the death situation after 24h, repeating each experiment for 3 times, and calculating the corrected death rate by using the following formula:
(4) method for determining aphids of broad beans
Dissolving a sample to be detected in dimethyl sulfoxide, diluting the sample to a certain concentration by using 0.1% Tween-80 aqueous solution, and taking a corresponding solution without the sample to be detected as a negative control. Collecting broad bean leaves with high insect population density, carefully selecting healthy 3-year-old aphids (30-40 heads) to stay on the leaf surfaces, immersing the broad bean leaves with the insects into a solution to be detected for 5s, taking the broad bean leaves away, draining the broad bean leaves, putting the broad bean leaves into a culture dish (6cm) with filter paper paved at the bottom, placing the broad bean leaves in a laboratory with the temperature of 22-24 ℃, the relative humidity of 60% and the illumination time of 14:10h for continuous feeding, recording the death condition after 24h, repeating each experiment for 3 times, and calculating the corrected death rate by using the following formula:
(5) results of the experiment
The insecticidal results of the compounds of the present invention are shown in table 1.
TABLE 1 poisoning Activity of Compounds of the invention against test pests
a: average of three replicates.
From Table 1 above, it is clear that the compounds of the present invention have a good poisoning activity against these pests.
Test example 2 measurement of bacteriostatic Activity of Compound of the present invention
(1) Test for plant pathogenic bacteria
Rice bacterial blight, cabbage soft rot, sweet potato pest, kiwifruit canker, and tobacco bacterial wilt.
(2) Measurement method
(a) Activation of strains: the bacterial strain to be tested is inoculated on a beef extract peptone solid medium slant and cultured overnight at 37 ℃.
(b) Preparation of bacterial suspension: inoculating a loop of activated test strain in a conical flask containing 100mL beef extract peptone liquid medium, culturing at 37 deg.C for 18h to obtain initial bacterial suspension, and diluting with sterile normal saline to appropriate concentration (10)6~107CFU/mL) of the suspension.
(c) Determination of Minimum Inhibitory Concentration (MIC): dissolving the test compound in dimethyl sulfoxide, diluting with sterile normal saline containing 0.1% Tween-80 by two-fold dilution method to obtain solutions with different concentrations, and mixing. 1mL of the diluted sample solution was added to 19mL of a sterilized medium, and mixed well to prepare a plate. After the culture medium has solidified, the above-mentioned concentration of 10% is added by coating method6And culturing 200 mu L of CFU/mL bacterial suspension at 37 ℃ for 16-18 h, observing the growth condition of bacteria, taking the concentration of completely sterile growth as the MIC value of the test sample solution, and taking the corresponding solution without the test compound as a blank control.
(3) Results of the experiment
The bacteriostatic activity of the compounds of the invention is shown in table 2.
TABLE 2 inhibitory Activity of the Compounds of the present invention against plant pathogenic bacteria
From the above table 2, it can be seen that the compounds of the present invention have a good inhibitory effect on these plant pathogenic bacteria.
In conclusion, the compound has better insecticidal activity and bactericidal activity, has better poisoning effect on pests, has better inhibition effect on plant pathogenic bacteria, and provides a new choice for agricultural insecticides and bactericides.
Claims (9)
2. The benzopyran-based compound according to claim 1, characterized in that: r1Is hydrogen atom, chlorine atom, bromine atom, methyl or methoxy; r2Is hydrogen atom, fluorine atom, chlorine atom, bromine atom, methyl or methoxyl.
3. The benzopyran-based compound according to claim 2, characterized in that: r1Is a hydrogen atom or a chlorine atom; r2Is fluorine atom, chlorine atom, methyl or methoxyl.
5. use of the benzopyran compounds according to any one of claims 1 to 4 in the preparation of agricultural fungicides.
6. Use of benzopyran compounds according to claim 5 in the preparation of agricultural fungicides, characterized in that: the bacteria for preventing and controlling the agricultural bactericide are bacteria.
7. Use of benzopyran compounds according to claim 5 in the preparation of agricultural fungicides, characterized in that: the bacteria controlled by the agricultural bactericide are rice bacterial blight, cabbage soft rot, sweet potato pest, kiwi fruit ulcer or tobacco bacterial wilt.
8. Use of the benzopyran compounds according to any one of claims 1 to 4 for the preparation of agricultural insecticides.
9. Use of benzopyran compounds according to claim 8, characterized in that: the pests controlled by the agricultural pesticide are armyworm, tetranychus cinnabarinus or aphis fabae.
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Citations (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4716238A (en) * | 1983-02-15 | 1987-12-29 | Alkaloida Vegyeszeti Gyar | Chromene derivatives useful as insecticides |
CN1204330A (en) * | 1995-10-13 | 1999-01-06 | 英国阿格里沃有限公司 | Heterocyclic fungicides |
JP2003176258A (en) * | 2001-09-18 | 2003-06-24 | Ishihara Sangyo Kaisha Ltd | Acid amide derivative, method for producing the same and noxious organism-exterminating agent |
CN102464643A (en) * | 2010-11-02 | 2012-05-23 | 西北农林科技大学农药研究所 | Flavonoid agricultural antibacterial compound |
CN104262239A (en) * | 2014-08-25 | 2015-01-07 | 浙江泰达作物科技有限公司 | A synthetic process of a green efficient agricultural fungicide |
CN106866600A (en) * | 2017-03-20 | 2017-06-20 | 贵州省果树科学研究所 | The compound and its derivative of one class preventing and control Kiwi berry soft rot |
CN107216305A (en) * | 2017-05-03 | 2017-09-29 | 中国人民解放军第四军医大学 | Benzopyran class compound and its application |
-
2021
- 2021-03-11 CN CN202110263879.9A patent/CN113004240B/en active Active
Patent Citations (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4716238A (en) * | 1983-02-15 | 1987-12-29 | Alkaloida Vegyeszeti Gyar | Chromene derivatives useful as insecticides |
CN1204330A (en) * | 1995-10-13 | 1999-01-06 | 英国阿格里沃有限公司 | Heterocyclic fungicides |
JP2003176258A (en) * | 2001-09-18 | 2003-06-24 | Ishihara Sangyo Kaisha Ltd | Acid amide derivative, method for producing the same and noxious organism-exterminating agent |
CN102464643A (en) * | 2010-11-02 | 2012-05-23 | 西北农林科技大学农药研究所 | Flavonoid agricultural antibacterial compound |
CN104262239A (en) * | 2014-08-25 | 2015-01-07 | 浙江泰达作物科技有限公司 | A synthetic process of a green efficient agricultural fungicide |
CN106866600A (en) * | 2017-03-20 | 2017-06-20 | 贵州省果树科学研究所 | The compound and its derivative of one class preventing and control Kiwi berry soft rot |
CN107216305A (en) * | 2017-05-03 | 2017-09-29 | 中国人民解放军第四军医大学 | Benzopyran class compound and its application |
Non-Patent Citations (4)
Title |
---|
JIAN-WU XIE等: "Efficient Method for the Synthesis of Optically Active 2-Amino-2-chromene Derivatives via One-Pot Tandem Reactions", 《ADV. SYNTH. CATAL.》 * |
LING-YU LI等: "A domino reaction for the synthesis of 2-amino-4H-chromene derivatives using bovine serum albumin as a catalyst", 《JOURNAL OF MOLECULAR CATALYSIS B: ENZYMATIC》 * |
YUAN-QIN ZHENG等: "Enantioselective synthesis of 2-amino-3-nitrile-chromenes catalyzed by cinchona alkaloids: A remarkable additive effect", 《CHINESE CHEMICAL LETTERS》 * |
王栋等: "8种4-甲基香豆素衍生物的合成及其农药活性", 《中国农学通报》 * |
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