CN109535136B - 2- [4- (2-furyl) ] pyrimidylurea compound and preparation method and application thereof - Google Patents
2- [4- (2-furyl) ] pyrimidylurea compound and preparation method and application thereof Download PDFInfo
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- CN109535136B CN109535136B CN201811604672.8A CN201811604672A CN109535136B CN 109535136 B CN109535136 B CN 109535136B CN 201811604672 A CN201811604672 A CN 201811604672A CN 109535136 B CN109535136 B CN 109535136B
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- reaction
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- furyl
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- 238000002360 preparation method Methods 0.000 title claims abstract description 14
- 239000001257 hydrogen Substances 0.000 claims abstract description 15
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 15
- 239000000575 pesticide Substances 0.000 claims abstract description 10
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims abstract description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 8
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims abstract description 4
- 125000004429 atom Chemical group 0.000 claims abstract description 4
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 4
- 125000001309 chloro group Chemical group Cl* 0.000 claims abstract description 4
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 4
- 125000001153 fluoro group Chemical group F* 0.000 claims abstract description 4
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims abstract description 4
- 229910052740 iodine Inorganic materials 0.000 claims abstract description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims abstract description 4
- 150000001875 compounds Chemical class 0.000 claims description 47
- 238000006243 chemical reaction Methods 0.000 claims description 36
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 30
- 239000000243 solution Substances 0.000 claims description 22
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 21
- 239000011259 mixed solution Substances 0.000 claims description 21
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 14
- 238000001914 filtration Methods 0.000 claims description 14
- 238000000034 method Methods 0.000 claims description 12
- 239000000203 mixture Substances 0.000 claims description 9
- 239000002808 molecular sieve Substances 0.000 claims description 9
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 claims description 9
- 240000008042 Zea mays Species 0.000 claims description 8
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 claims description 8
- 235000002017 Zea mays subsp mays Nutrition 0.000 claims description 8
- 235000005822 corn Nutrition 0.000 claims description 8
- HYBBIBNJHNGZAN-UHFFFAOYSA-N furfural Chemical compound O=CC1=CC=CO1 HYBBIBNJHNGZAN-UHFFFAOYSA-N 0.000 claims description 8
- KNIKDPRISVIPBU-UHFFFAOYSA-N 1,2-dichloro-4-[isocyano-(4-methylphenyl)sulfonylmethyl]benzene Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C([N+]#[C-])C1=CC=C(Cl)C(Cl)=C1 KNIKDPRISVIPBU-UHFFFAOYSA-N 0.000 claims description 7
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 7
- 239000000706 filtrate Substances 0.000 claims description 7
- 239000005457 ice water Substances 0.000 claims description 7
- 230000007935 neutral effect Effects 0.000 claims description 7
- 239000002244 precipitate Substances 0.000 claims description 7
- 239000011541 reaction mixture Substances 0.000 claims description 7
- 239000000741 silica gel Substances 0.000 claims description 7
- 229910002027 silica gel Inorganic materials 0.000 claims description 7
- 238000003756 stirring Methods 0.000 claims description 7
- 238000005406 washing Methods 0.000 claims description 7
- OUDFNZMQXZILJD-UHFFFAOYSA-N 5-methyl-2-furaldehyde Chemical compound CC1=CC=C(C=O)O1 OUDFNZMQXZILJD-UHFFFAOYSA-N 0.000 claims description 5
- 230000008569 process Effects 0.000 claims description 4
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Natural products CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 claims description 3
- 150000008062 acetophenones Chemical class 0.000 claims description 3
- 241000254173 Coleoptera Species 0.000 claims description 2
- 241000406668 Loxodonta cyclotis Species 0.000 claims description 2
- 241000607479 Yersinia pestis Species 0.000 abstract description 10
- 244000000005 bacterial plant pathogen Species 0.000 abstract description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 abstract description 5
- 230000002401 inhibitory effect Effects 0.000 abstract description 4
- 230000000607 poisoning effect Effects 0.000 abstract description 3
- 150000001408 amides Chemical class 0.000 abstract description 2
- 150000003230 pyrimidines Chemical class 0.000 abstract description 2
- -1 pyrimidyl urea compound Chemical class 0.000 abstract description 2
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 abstract 2
- 239000004202 carbamide Substances 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 238000005507 spraying Methods 0.000 abstract 1
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 20
- 238000001228 spectrum Methods 0.000 description 14
- 239000000047 product Substances 0.000 description 11
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 10
- 230000001580 bacterial effect Effects 0.000 description 10
- 229910052799 carbon Inorganic materials 0.000 description 10
- 238000001819 mass spectrum Methods 0.000 description 7
- NTPLXRHDUXRPNE-UHFFFAOYSA-N 4-methoxyacetophenone Chemical compound COC1=CC=C(C(C)=O)C=C1 NTPLXRHDUXRPNE-UHFFFAOYSA-N 0.000 description 6
- 230000000844 anti-bacterial effect Effects 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 5
- 238000005160 1H NMR spectroscopy Methods 0.000 description 5
- 239000003899 bactericide agent Substances 0.000 description 5
- 230000004071 biological effect Effects 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 230000000749 insecticidal effect Effects 0.000 description 5
- 230000003595 spectral effect Effects 0.000 description 5
- GNKZMNRKLCTJAY-UHFFFAOYSA-N 4'-Methylacetophenone Chemical compound CC(=O)C1=CC=C(C)C=C1 GNKZMNRKLCTJAY-UHFFFAOYSA-N 0.000 description 4
- 238000011160 research Methods 0.000 description 4
- 239000012265 solid product Substances 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- BUZYGTVTZYSBCU-UHFFFAOYSA-N 1-(4-chlorophenyl)ethanone Chemical compound CC(=O)C1=CC=C(Cl)C=C1 BUZYGTVTZYSBCU-UHFFFAOYSA-N 0.000 description 3
- 230000003385 bacteriostatic effect Effects 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 239000002917 insecticide Substances 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 238000003860 storage Methods 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 244000291564 Allium cepa Species 0.000 description 2
- 235000002732 Allium cepa var. cepa Nutrition 0.000 description 2
- 241001149961 Alternaria brassicae Species 0.000 description 2
- 241000207199 Citrus Species 0.000 description 2
- 244000241257 Cucumis melo Species 0.000 description 2
- 235000015510 Cucumis melo subsp melo Nutrition 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 239000001888 Peptone Substances 0.000 description 2
- 108010080698 Peptones Proteins 0.000 description 2
- 241000471406 Physoderma maydis Species 0.000 description 2
- 241000233647 Phytophthora nicotianae var. parasitica Species 0.000 description 2
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 244000061456 Solanum tuberosum Species 0.000 description 2
- 235000002595 Solanum tuberosum Nutrition 0.000 description 2
- FJJCIZWZNKZHII-UHFFFAOYSA-N [4,6-bis(cyanoamino)-1,3,5-triazin-2-yl]cyanamide Chemical compound N#CNC1=NC(NC#N)=NC(NC#N)=N1 FJJCIZWZNKZHII-UHFFFAOYSA-N 0.000 description 2
- 230000009471 action Effects 0.000 description 2
- 235000015278 beef Nutrition 0.000 description 2
- 230000033228 biological regulation Effects 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 235000020971 citrus fruits Nutrition 0.000 description 2
- 238000012258 culturing Methods 0.000 description 2
- 238000007865 diluting Methods 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 235000013399 edible fruits Nutrition 0.000 description 2
- 238000004134 energy conservation Methods 0.000 description 2
- 238000005265 energy consumption Methods 0.000 description 2
- 230000012010 growth Effects 0.000 description 2
- 239000001963 growth medium Substances 0.000 description 2
- 150000002391 heterocyclic compounds Chemical class 0.000 description 2
- 231100000053 low toxicity Toxicity 0.000 description 2
- 238000000691 measurement method Methods 0.000 description 2
- 239000002609 medium Substances 0.000 description 2
- 238000005580 one pot reaction Methods 0.000 description 2
- 235000019319 peptone Nutrition 0.000 description 2
- 230000008635 plant growth Effects 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 241000894006 Bacteria Species 0.000 description 1
- 241000254171 Curculionidae Species 0.000 description 1
- 206010059866 Drug resistance Diseases 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 241000254113 Tribolium castaneum Species 0.000 description 1
- 241000209140 Triticum Species 0.000 description 1
- 235000021307 Triticum Nutrition 0.000 description 1
- 230000000895 acaricidal effect Effects 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 230000001093 anti-cancer Effects 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 230000003064 anti-oxidating effect Effects 0.000 description 1
- 230000000259 anti-tumor effect Effects 0.000 description 1
- 230000000840 anti-viral effect Effects 0.000 description 1
- 230000002155 anti-virotic effect Effects 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 235000012791 bagels Nutrition 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
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- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 1
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- 238000010267 two-fold dilution method Methods 0.000 description 1
- 238000009333 weeding Methods 0.000 description 1
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Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- 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
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
- A01N47/36—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the group >N—CO—N< directly attached to at least one heterocyclic ring; Thio analogues thereof
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- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Dentistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Plant Pathology (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Plural Heterocyclic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
Description
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Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
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CN201811604672.8A CN109535136B (en) | 2018-12-26 | 2018-12-26 | 2- [4- (2-furyl) ] pyrimidylurea compound and preparation method and application thereof |
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CN201811604672.8A CN109535136B (en) | 2018-12-26 | 2018-12-26 | 2- [4- (2-furyl) ] pyrimidylurea compound and preparation method and application thereof |
Publications (2)
Publication Number | Publication Date |
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CN109535136A CN109535136A (en) | 2019-03-29 |
CN109535136B true CN109535136B (en) | 2022-01-14 |
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CN201811604672.8A Active CN109535136B (en) | 2018-12-26 | 2018-12-26 | 2- [4- (2-furyl) ] pyrimidylurea compound and preparation method and application thereof |
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Families Citing this family (1)
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CN111116422A (en) * | 2019-12-30 | 2020-05-08 | 西南大学 | Paeonol etherified urea compound with anti-inflammatory activity and application thereof |
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2018
- 2018-12-26 CN CN201811604672.8A patent/CN109535136B/en active Active
Non-Patent Citations (8)
Title |
---|
Chen, Wei,等.Synthesis and evaluation of novel N-(4’-arylpyrimidin-2’-yl) sulfonylurea derivatives as potential antifungal agents.《Chem. Res. Chin. Univ.》.2015,第31卷(第2期),第218-223页. * |
N-(4-’芳环取代嘧啶基-2’-基)-2-乙氧羰基苯磺酰脲衍生物的合成及抑菌活性;刘卓,等;《高等学校化学学报》;20130831;第34卷(第8期);第1868-1872页 * |
NOVEL MONOCYCLIC β-LACTUM MOLECULES: DESIGNED AND CHARACTERIZED AS POSSIBLE ANTIBACTERIAL AGENTS;Vikas A. Desai,等;《World Journal of Pharmaceutical Research》;20161231;第5卷(第4期);第1943-1950页 * |
Shah, Tejaskumar J.,等.Synthesis of some novel fluorinated 4-thiazolidinones containing amide linkages and their antimicrobial screening.《ARKIVOC》.2007,第218-228页. * |
Synthesis and evaluation of novel N-(4’-arylpyrimidin-2’-yl) sulfonylurea derivatives as potential antifungal agents;Chen, Wei,等;《Chem. Res. Chin. Univ.》;20151231;第31卷(第2期);第218-223页 * |
Synthesis of some novel fluorinated 4-thiazolidinones containing amide linkages and their antimicrobial screening;Shah, Tejaskumar J.,等;《ARKIVOC》;20071231;第218-228页 * |
Vikas A. Desai,等.NOVEL MONOCYCLIC β-LACTUM MOLECULES: DESIGNED AND CHARACTERIZED AS POSSIBLE ANTIBACTERIAL AGENTS.《World Journal of Pharmaceutical Research》.2016,第5卷(第4期),第1943-1950页. * |
刘卓,等.N-(4-’芳环取代嘧啶基-2’-基)-2-乙氧羰基苯磺酰脲衍生物的合成及抑菌活性.《高等学校化学学报》.2013,第34卷(第8期),第1868-1872页. * |
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Effective date of registration: 20231011 Address after: 2081, building a, 88 Jianghai West Road, Liangxi District, Wuxi City, Jiangsu Province, 214000 Patentee after: Wuxi Xiangyuan Information Technology Co.,Ltd. Address before: 610039, No. 999, Jin Zhou road, Jinniu District, Sichuan, Chengdu Patentee before: XIHUA University Effective date of registration: 20231011 Address after: 400000 Shimahe chemical village, Jiangbei District, Chongqing Patentee after: Chongqing Chemical Research Institute Co.,Ltd. Patentee after: Chongqing Chemical Research Institute Materials Technology Co.,Ltd. Address before: 2081, building a, 88 Jianghai West Road, Liangxi District, Wuxi City, Jiangsu Province, 214000 Patentee before: Wuxi Xiangyuan Information Technology Co.,Ltd. |