CN116199643A - Phenothiazine compound containing isopropanol substructure, and preparation and application thereof - Google Patents
Phenothiazine compound containing isopropanol substructure, and preparation and application thereof Download PDFInfo
- Publication number
- CN116199643A CN116199643A CN202310059923.3A CN202310059923A CN116199643A CN 116199643 A CN116199643 A CN 116199643A CN 202310059923 A CN202310059923 A CN 202310059923A CN 116199643 A CN116199643 A CN 116199643A
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- China
- Prior art keywords
- optionally substituted
- methyl
- unsubstituted
- isopropanol
- substructure
- Prior art date
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- -1 Phenothiazine compound Chemical class 0.000 title claims abstract description 63
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 title claims abstract description 52
- 229950000688 phenothiazine Drugs 0.000 title claims abstract description 18
- 238000002360 preparation method Methods 0.000 title claims abstract description 16
- 150000001875 compounds Chemical class 0.000 claims abstract description 42
- 230000001580 bacterial effect Effects 0.000 claims abstract description 30
- 201000010099 disease Diseases 0.000 claims abstract description 25
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 25
- 241000196324 Embryophyta Species 0.000 claims abstract description 22
- 240000007594 Oryza sativa Species 0.000 claims abstract description 11
- 235000007164 Oryza sativa Nutrition 0.000 claims abstract description 11
- 235000009566 rice Nutrition 0.000 claims abstract description 11
- 240000008067 Cucumis sativus Species 0.000 claims abstract description 10
- 235000010799 Cucumis sativus var sativus Nutrition 0.000 claims abstract description 10
- 244000298697 Actinidia deliciosa Species 0.000 claims abstract description 7
- 235000009436 Actinidia deliciosa Nutrition 0.000 claims abstract description 7
- 241000207199 Citrus Species 0.000 claims abstract description 7
- 235000020971 citrus fruits Nutrition 0.000 claims abstract description 7
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- 241000233622 Phytophthora infestans Species 0.000 claims abstract description 4
- 235000016761 Piper aduncum Nutrition 0.000 claims abstract description 4
- 235000017804 Piper guineense Nutrition 0.000 claims abstract description 4
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- 239000000203 mixture Substances 0.000 claims description 20
- 229910052739 hydrogen Inorganic materials 0.000 claims description 17
- 239000001257 hydrogen Substances 0.000 claims description 17
- 150000002431 hydrogen Chemical class 0.000 claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- 125000003118 aryl group Chemical group 0.000 claims description 12
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 12
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- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 6
- 235000007688 Lycopersicon esculentum Nutrition 0.000 claims description 6
- 208000031888 Mycoses Diseases 0.000 claims description 6
- 240000003768 Solanum lycopersicum Species 0.000 claims description 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 6
- 229910052805 deuterium Inorganic materials 0.000 claims description 6
- 125000001207 fluorophenyl group Chemical group 0.000 claims description 6
- 239000000843 powder Substances 0.000 claims description 6
- 230000003612 virological effect Effects 0.000 claims description 6
- 238000006243 chemical reaction Methods 0.000 claims description 5
- 239000003795 chemical substances by application Substances 0.000 claims description 5
- 125000006282 2-chlorobenzyl group Chemical group [H]C1=C([H])C(Cl)=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 4
- 239000000779 smoke Substances 0.000 claims description 4
- 125000006280 2-bromobenzyl group Chemical group [H]C1=C([H])C(Br)=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
- 125000004847 2-fluorobenzyl group Chemical group [H]C1=C([H])C(F)=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 3
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 3
- 125000006279 3-bromobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(Br)=C1[H])C([H])([H])* 0.000 claims description 3
- 125000003852 3-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(Cl)=C1[H])C([H])([H])* 0.000 claims description 3
- 125000006284 3-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(F)=C1[H])C([H])([H])* 0.000 claims description 3
- 125000006291 3-hydroxybenzyl group Chemical group [H]OC1=C([H])C([H])=C([H])C(=C1[H])C([H])([H])* 0.000 claims description 3
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 3
- 125000006281 4-bromobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Br)C([H])([H])* 0.000 claims description 3
- 125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 claims description 3
- 125000004176 4-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1F)C([H])([H])* 0.000 claims description 3
- 125000003143 4-hydroxybenzyl group Chemical group [H]C([*])([H])C1=C([H])C([H])=C(O[H])C([H])=C1[H] 0.000 claims description 3
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 3
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 3
- 125000001313 C5-C10 heteroaryl group Chemical group 0.000 claims description 3
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- 241000702632 Rice dwarf virus Species 0.000 claims description 3
- 235000009754 Vitis X bourquina Nutrition 0.000 claims description 3
- 235000012333 Vitis X labruscana Nutrition 0.000 claims description 3
- 240000006365 Vitis vinifera Species 0.000 claims description 3
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- 125000003342 alkenyl group Chemical group 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000000304 alkynyl group Chemical group 0.000 claims description 3
- 235000001014 amino acid Nutrition 0.000 claims description 3
- 229940024606 amino acid Drugs 0.000 claims description 3
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- 125000004799 bromophenyl group Chemical group 0.000 claims description 3
- 125000004369 butenyl group Chemical group C(=CCC)* 0.000 claims description 3
- 125000000480 butynyl group Chemical group [*]C#CC([H])([H])C([H])([H])[H] 0.000 claims description 3
- 125000000068 chlorophenyl group Chemical group 0.000 claims description 3
- 239000004495 emulsifiable concentrate Substances 0.000 claims description 3
- 239000000839 emulsion Substances 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 239000008187 granular material Substances 0.000 claims description 3
- 125000006038 hexenyl group Chemical group 0.000 claims description 3
- 125000005980 hexynyl group Chemical group 0.000 claims description 3
- 125000004464 hydroxyphenyl group Chemical group 0.000 claims description 3
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 3
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
- 235000010485 konjac Nutrition 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- HRDXJKGNWSUIBT-UHFFFAOYSA-N methoxybenzene Chemical group [CH2]OC1=CC=CC=C1 HRDXJKGNWSUIBT-UHFFFAOYSA-N 0.000 claims description 3
- 239000003094 microcapsule Substances 0.000 claims description 3
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000001624 naphthyl group Chemical group 0.000 claims description 3
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 claims description 3
- 125000005981 pentynyl group Chemical group 0.000 claims description 3
- 125000005561 phenanthryl group Chemical group 0.000 claims description 3
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 claims description 3
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 claims description 3
- UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical compound OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 claims description 3
- 125000004076 pyridyl group Chemical group 0.000 claims description 3
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
- 239000007921 spray Substances 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- 239000000375 suspending agent Substances 0.000 claims description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
- 125000003944 tolyl group Chemical group 0.000 claims description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 3
- 239000004562 water dispersible granule Substances 0.000 claims description 3
- 239000004563 wettable powder Substances 0.000 claims description 3
- 125000006290 2-hydroxybenzyl group Chemical group [H]OC1=C(C([H])=C([H])C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- GRFNBEZIAWKNCO-UHFFFAOYSA-N 3-pyridinol Chemical compound OC1=CC=CN=C1 GRFNBEZIAWKNCO-UHFFFAOYSA-N 0.000 claims description 2
- GCNTZFIIOFTKIY-UHFFFAOYSA-N 4-hydroxypyridine Chemical compound OC1=CC=NC=C1 GCNTZFIIOFTKIY-UHFFFAOYSA-N 0.000 claims description 2
- KQSSATDQUYCRGS-UHFFFAOYSA-N methyl glycinate Chemical group COC(=O)CN KQSSATDQUYCRGS-UHFFFAOYSA-N 0.000 claims description 2
- 239000004475 Arginine Substances 0.000 claims 1
- DCXYFEDJOCDNAF-UHFFFAOYSA-N Asparagine Natural products OC(=O)C(N)CC(N)=O DCXYFEDJOCDNAF-UHFFFAOYSA-N 0.000 claims 1
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- ROHFNLRQFUQHCH-UHFFFAOYSA-N Leucine Natural products CC(C)CC(N)C(O)=O ROHFNLRQFUQHCH-UHFFFAOYSA-N 0.000 claims 1
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- 239000004472 Lysine Substances 0.000 claims 1
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- AYFVYJQAPQTCCC-UHFFFAOYSA-N Threonine Natural products CC(O)C(N)C(O)=O AYFVYJQAPQTCCC-UHFFFAOYSA-N 0.000 claims 1
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- QIVBCDIJIAJPQS-UHFFFAOYSA-N Tryptophan Natural products C1=CC=C2C(CC(N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-UHFFFAOYSA-N 0.000 claims 1
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- 235000004279 alanine Nutrition 0.000 claims 1
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- OQFSQFPPLPISGP-UHFFFAOYSA-N beta-carboxyaspartic acid Natural products OC(=O)C(N)C(C(O)=O)C(O)=O OQFSQFPPLPISGP-UHFFFAOYSA-N 0.000 claims 1
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- QVDXUKJJGUSGLS-LURJTMIESA-N methyl L-leucinate Chemical compound COC(=O)[C@@H](N)CC(C)C QVDXUKJJGUSGLS-LURJTMIESA-N 0.000 description 2
- KPNBUPJZFJCCIQ-LURJTMIESA-N methyl L-lysinate Chemical compound COC(=O)[C@@H](N)CCCCN KPNBUPJZFJCCIQ-LURJTMIESA-N 0.000 description 2
- VSDUZFOSJDMAFZ-VIFPVBQESA-N methyl L-phenylalaninate Chemical compound COC(=O)[C@@H](N)CC1=CC=CC=C1 VSDUZFOSJDMAFZ-VIFPVBQESA-N 0.000 description 2
- MWZPENIJLUWBSY-VIFPVBQESA-N methyl L-tyrosinate Chemical compound COC(=O)[C@@H](N)CC1=CC=C(O)C=C1 MWZPENIJLUWBSY-VIFPVBQESA-N 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 239000010413 mother solution Substances 0.000 description 2
- 230000001681 protective effect Effects 0.000 description 2
- 235000018102 proteins Nutrition 0.000 description 2
- 102000004169 proteins and genes Human genes 0.000 description 2
- 108090000623 proteins and genes Proteins 0.000 description 2
- 238000012827 research and development Methods 0.000 description 2
- HBMJWWWQQXIZIP-UHFFFAOYSA-N silicon carbide Chemical compound [Si+]#[C-] HBMJWWWQQXIZIP-UHFFFAOYSA-N 0.000 description 2
- 229910010271 silicon carbide Inorganic materials 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Substances C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- FDKWRPBBCBCIGA-REOHCLBHSA-N (2r)-2-azaniumyl-3-$l^{1}-selanylpropanoate Chemical compound [Se]C[C@H](N)C(O)=O FDKWRPBBCBCIGA-REOHCLBHSA-N 0.000 description 1
- FXVNBZGTAWLLNE-UHFFFAOYSA-N 1,3-thiazole;zinc Chemical compound [Zn].C1=CSC=N1 FXVNBZGTAWLLNE-UHFFFAOYSA-N 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical class [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- 239000005730 Azoxystrobin Substances 0.000 description 1
- FDKWRPBBCBCIGA-UWTATZPHSA-N D-Selenocysteine Natural products [Se]C[C@@H](N)C(O)=O FDKWRPBBCBCIGA-UWTATZPHSA-N 0.000 description 1
- 241000233866 Fungi Species 0.000 description 1
- 238000012404 In vitro experiment Methods 0.000 description 1
- 239000005868 Metconazole Substances 0.000 description 1
- 229920001213 Polysorbate 20 Polymers 0.000 description 1
- IWUCXVSUMQZMFG-AFCXAGJDSA-N Ribavirin Chemical compound N1=C(C(=O)N)N=CN1[C@H]1[C@H](O)[C@H](O)[C@@H](CO)O1 IWUCXVSUMQZMFG-AFCXAGJDSA-N 0.000 description 1
- 244000061456 Solanum tuberosum Species 0.000 description 1
- 235000002595 Solanum tuberosum Nutrition 0.000 description 1
- 229930195482 Validamycin Natural products 0.000 description 1
- 241000589634 Xanthomonas Species 0.000 description 1
- 241000907138 Xanthomonas oryzae pv. oryzae Species 0.000 description 1
- 239000003443 antiviral agent Substances 0.000 description 1
- 239000012752 auxiliary agent Substances 0.000 description 1
- WFDXOXNFNRHQEC-GHRIWEEISA-N azoxystrobin Chemical compound CO\C=C(\C(=O)OC)C1=CC=CC=C1OC1=CC(OC=2C(=CC=CC=2)C#N)=NC=N1 WFDXOXNFNRHQEC-GHRIWEEISA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 235000021186 dishes Nutrition 0.000 description 1
- GKIPXFAANLTWBM-UHFFFAOYSA-N epibromohydrin Chemical compound BrCC1CO1 GKIPXFAANLTWBM-UHFFFAOYSA-N 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 244000053095 fungal pathogen Species 0.000 description 1
- 235000001727 glucose Nutrition 0.000 description 1
- 230000009036 growth inhibition Effects 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 231100000086 high toxicity Toxicity 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000011081 inoculation Methods 0.000 description 1
- PVTHJAPFENJVNC-MHRBZPPQSA-N kasugamycin Chemical compound N[C@H]1C[C@H](NC(=N)C(O)=O)[C@@H](C)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@H](O)[C@@H]1O PVTHJAPFENJVNC-MHRBZPPQSA-N 0.000 description 1
- 230000000670 limiting effect Effects 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- XWPZUHJBOLQNMN-UHFFFAOYSA-N metconazole Chemical compound C1=NC=NN1CC1(O)C(C)(C)CCC1CC1=CC=C(Cl)C=C1 XWPZUHJBOLQNMN-UHFFFAOYSA-N 0.000 description 1
- ZRGVTTCCASYOFN-UHFFFAOYSA-N methyl 2-(methylideneamino)acetate Chemical compound COC(=O)CN=C ZRGVTTCCASYOFN-UHFFFAOYSA-N 0.000 description 1
- 230000000813 microbial effect Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 229910000402 monopotassium phosphate Inorganic materials 0.000 description 1
- 235000019796 monopotassium phosphate Nutrition 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 230000036961 partial effect Effects 0.000 description 1
- PJNZPQUBCPKICU-UHFFFAOYSA-N phosphoric acid;potassium Chemical compound [K].OP(O)(O)=O PJNZPQUBCPKICU-UHFFFAOYSA-N 0.000 description 1
- 244000000003 plant pathogen Species 0.000 description 1
- 239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 description 1
- 235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 description 1
- 239000013641 positive control Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 229960000329 ribavirin Drugs 0.000 description 1
- HZCAHMRRMINHDJ-DBRKOABJSA-N ribavirin Natural products O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1N=CN=C1 HZCAHMRRMINHDJ-DBRKOABJSA-N 0.000 description 1
- ZKZBPNGNEQAJSX-UHFFFAOYSA-N selenocysteine Natural products [SeH]CC(N)C(O)=O ZKZBPNGNEQAJSX-UHFFFAOYSA-N 0.000 description 1
- 235000016491 selenocysteine Nutrition 0.000 description 1
- 229940055619 selenocysteine Drugs 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- WJCNZQLZVWNLKY-UHFFFAOYSA-N thiabendazole Chemical compound S1C=NC(C=2NC3=CC=CC=C3N=2)=C1 WJCNZQLZVWNLKY-UHFFFAOYSA-N 0.000 description 1
- 239000004308 thiabendazole Substances 0.000 description 1
- 229960004546 thiabendazole Drugs 0.000 description 1
- 235000010296 thiabendazole Nutrition 0.000 description 1
- JZRWCGZRTZMZEH-UHFFFAOYSA-N thiamine Chemical compound CC1=C(CCO)SC=[N+]1CC1=CN=C(C)N=C1N JZRWCGZRTZMZEH-UHFFFAOYSA-N 0.000 description 1
- JARYYMUOCXVXNK-IMTORBKUSA-N validamycin Chemical compound N([C@H]1C[C@@H]([C@H]([C@H](O)[C@H]1O)O[C@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)O)CO)[C@H]1C=C(CO)[C@H](O)[C@H](O)[C@H]1O JARYYMUOCXVXNK-IMTORBKUSA-N 0.000 description 1
- 210000003462 vein Anatomy 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D279/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one sulfur atom as the only ring hetero atoms
- C07D279/10—1,4-Thiazines; Hydrogenated 1,4-thiazines
- C07D279/14—1,4-Thiazines; Hydrogenated 1,4-thiazines condensed with carbocyclic rings or ring systems
- C07D279/18—[b, e]-condensed with two six-membered rings
- C07D279/22—[b, e]-condensed with two six-membered rings with carbon atoms directly attached to the ring nitrogen atom
- C07D279/24—[b, e]-condensed with two six-membered rings with carbon atoms directly attached to the ring nitrogen atom with hydrocarbon radicals, substituted by amino radicals, attached to the ring nitrogen atom
- C07D279/26—[b, e]-condensed with two six-membered rings with carbon atoms directly attached to the ring nitrogen atom with hydrocarbon radicals, substituted by amino radicals, attached to the ring nitrogen atom without other substituents attached to the ring system
-
- 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
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/84—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms six-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,4
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
- A01P1/00—Disinfectants; Antimicrobial compounds or mixtures thereof
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
- A01P3/00—Fungicides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Environmental Sciences (AREA)
- Wood Science & Technology (AREA)
- Plant Pathology (AREA)
- Zoology (AREA)
- Engineering & Computer Science (AREA)
- Pest Control & Pesticides (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Dentistry (AREA)
- Health & Medical Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Microbiology (AREA)
- Mycology (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
The invention relates to the technical field of pharmaceutical chemistry, in particular to a phenothiazine compound containing an isopropanol substructure, and preparation and application thereof. The specific technical scheme is as follows: based on phenothiazine, isopropanol is taken as a bridge group, and structural fragments containing amino or alcoholic hydroxyl groups are introduced into a system of a structural formula (I), so that a series of phenothiazine compounds containing isopropanol substructure are synthesized, and the compounds have excellent inhibition effects on plant pathogenic bacteria (such as rice bacterial leaf blight, citrus canker, kiwi fruit canker) and plant virus diseases (such as tobacco mosaic virus, cucumber mosaic virus, rice stripe dwarf and the like) and plant pathogenic fungi (such as cucumber gray mold, pepper wilt, rape sclerotinia, wheat scab, potato late blight, rice sheath blight) and the like.
Description
Technical Field
The invention relates to the technical field of pharmaceutical chemistry, in particular to a phenothiazine compound containing an isopropanol substructure, and preparation and application thereof.
Background
Plant diseases have become one of the important reasons for limiting the yield of agricultural or commercial crops. Crop losses per year due to plant disease are statistically over 2200 billion dollars, and unpredictable plant disease can even lead to particulate failure in certain areas. Pesticides, which are important production data, have been an important selection means for controlling the development of plant diseases. However, a single bactericidal or antiviral agent (such as thiabendazole, zinc thiazole, metconazole, validamycin, kasugamycin, ningnanmycin, ribavirin, etc.) is administered for a long period of time. These measures are not only costly, causing serious pollution, but also significantly increasing the resistance to plant pathogens. On the other hand, the high toxicity of traditional pesticides is caused by the fact that part of the pesticides are forbidden to be produced and used because the pesticides remain in the environment and in foods of people. Therefore, development of a novel green pesticide having high activity and high selectivity is urgently required.
Disclosure of Invention
Aiming at the defects of the prior art, the invention provides a phenothiazine compound containing an isopropanol substructure, and preparation and application thereof, wherein phenothiazine is taken as a matrix, different active functional groups are introduced into the system by using the isopropanol substructure, a series of phenothiazine compounds with isopropanol substructure are synthesized, the bioactivity of the compounds is inspected, and an important scientific basis is provided for the research and development and the creation of new pesticides.
In order to achieve the above purpose, the invention is realized by the following technical scheme:
the invention discloses a phenothiazine compound containing an isopropanol substructure, which has a structural general formula shown as (I):
wherein R is 1 Is any one of hydrogen, optionally substituted or unsubstituted alkyl, optionally substituted or unsubstituted aryl, optionally substituted or unsubstituted benzyl, and optionally substituted or unsubstituted heteroaryl;
R 2 is any one of hydrogen, optionally substituted or unsubstituted alkyl, optionally substituted or unsubstituted aryl, optionally substituted or unsubstituted benzyl, and optionally substituted or unsubstituted heteroaryl;
x is O, S or N.
Preferably, R 1 And R is 2 Each independently is any one of hydrogen, deuterium, optionally substituted or unsubstituted alkyl, optionally substituted or unsubstituted alkenyl, optionally substituted or unsubstituted alkynyl, optionally substituted or unsubstituted alkoxy, optionally substituted or unsubstituted cycloalkyl, optionally substituted or unsubstituted aryl, optionally substituted or unsubstituted heteroaryl.
Preferably, R 1 And R is 2 Independently hydrogen, optionally substituted or unsubstituted C 1 -C 16 Alkyl, optionally substituted or unsubstituted C 2 -C 6 Alkenyl, optionally substituted or unsubstituted C 2 -C 6 Alkynyl, optionally substituted or unsubstituted C 5 -C 10 Cycloalkyl, optionally substituted or unsubstituted C 5 -C 10 Aryl, optionally substituted or unsubstituted C 5 -C 10 Heteroaryl, optionally substituted or unsubstituted benzyl, methyl amino acid, optionally substituted or unsubstituted 1,2, 4-triazole thioether.
Preferably, R 1 And R is 2 Independently hydrogen, deuterium, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, neopentyl, ethenyl, propenyl, allyl, butenyl, pentenyl, hexenyl, propynyl, butynyl, pentynyl, hexynyl, methoxy, ethoxy, propoxy, butoxy, phenyl, chlorophenyl, bromophenyl, fluorophenyl, tolyl, aminophenyl, hydroxyphenyl, benzyl, o-fluorobenzyl, m-fluorobenzyl, p-fluorobenzyl, o-chlorobenzyl, m-chlorobenzyl, p-chlorobenzyl, o-bromobenzyl, m-bromobenzyl, p-bromobenzyl, naphthyl, phenanthryl, pyridyl, o-fluoropyridyl, m-fluoropyridyl, o-bromopyridyl, m-bromopyridyl, o-chloropyridyl, m-chloropyridyl, o-fluorothienyl, m-fluorothienyl, o-fluorofuryl, o-fluorotetrahydrofuryl, o-bromopyridyl m-fluorofuranyl, m-fluorotetrahydrofuranyl, o-bromothienyl, m-bromothienyl, o-bromofuranyl, m-bromofuranyl, o-bromotetrahydrofuranyl, m-bromotetrahydrofuranyl, o-chlorothiophene, m-chlorothiophene, o-chlorofuranyl, m-chlorotetrahydrofuranyl, o-hydroxybenzyl, m-hydroxybenzyl, p-hydroxybenzyl, o-aminobenzyl, m-aminobenzyl, p-aminobenzyl, o-methylbenzyl, p-methylbenzyl, o-hydroxypyridine, m-hydroxypyridyl, p-hydroxypyridyl, o-aminothiophene, m-aminothiophene, o-hydroxyfuryl, m-hydroxyfuryl, o-hydroxytetrahydrofuranyl, m-hydroxytetrahydrofuranyl, o-methylfuryl, m-methylfuryl, o-methyltetrahydrofuranyl, o-furanmethylene, m-furanmethylene, O-tetrahydrofuran methylene, m-tetrahydrofuran methylene, glycine methyl ester, alanine methyl ester, valine methyl ester, leucine methyl ester, isoleucine methyl ester, methionine methyl ester, proline methyl ester, tryptophan methyl ester, serine methyl ester, tyrosine methyl ester, cysteine methyl ester, phenylalanine methyl ester, asparagine methyl ester, glutamine methyl ester, threonine methyl ester, aspartic acid methyl ester, glutamic acid methyl ester, lysine methyl ester, arginine methyl ester, histidine methyl ester,Selenium cysteine methyl ester, pyrrolysine methyl ester, 4-amino-5-methyl-4H-1, 2, 4-triazole-3-thioether, 4-amino-5-isopropyl-4H-1, 2, 4-triazole-3-thioether, 4-amino-5-phenyl-4H-1, 2, 4-triazole-3-thioether, 4-amino-5- (pyridin-3-yl) -4H-1,2, 4-triazole-3-thioether, 4-amino-5- (pyridin-2-yl) -4H-1,2, 4-triazole-3-thioether, 4-amino-5- (fluorophenyl) -4H-1,2, 4-triazole-3-thioether, and 4-amino-5- (phenoxymethyl) -4H-1,2, 4-triazole-3-thioether.
Correspondingly, the preparation method of the phenothiazine compound containing the isopropanol substructure has the following reaction general formula:
correspondingly, the composition containing the compound or the compound prepared by the preparation method is in the form of emulsifiable concentrate, wettable powder, granules, water aqua, suspending agent, ultra-low volume spray, soluble powder, microcapsule, smoke agent, aqueous emulsion or water dispersible granule.
Correspondingly, the application of the compound or the compound prepared by the preparation method or the composition in controlling agricultural diseases and insect pests.
Preferably, the agricultural pest is a plant bacterial disease and/or a plant fungal disease and/or a plant viral disease.
Preferably, the bacterial diseases are rice bacterial leaf blight, cucumber bacterial leaf blight, konjak bacterial leaf blight, citrus canker, tobacco bacterial wilt, grape canker, tomato canker, kiwi fruit canker and apple canker; and/or the fungal diseases are cucumber gray mold, pepper blight, rape sclerotinia, wheat scab, potato late blight and rice sheath blight; and/or the viral diseases are tobacco mosaic disease, tomato mosaic disease, cucumber mosaic disease and rice dwarf disease.
Correspondingly, the application method of the compound or the compound prepared by the preparation method or the composition is characterized in that: the compound or composition is applied to a pest or an environment in which it is living, or is directly contacted with plants.
The invention has the following beneficial effects:
according to the invention, based on phenothiazine and isopropanol as a bridge group, structural fragments containing amino or alcoholic hydroxyl groups are introduced into a structural formula (I) system to synthesize a series of phenothiazine compounds containing isopropanol substructure, and the compounds have good to excellent inhibition effects on plant pathogenic bacteria (such as rice bacterial blight bacteria (Xanthomonas oryzae pv. Oryzae, xoo), citrus canker (Xanthomonas axotosporp v. Citri, xac) and kiwi fruit canker (Pseudomouas syringae pv. Aeeiuidae, psa) and the like), tobacco mosaic virus, plant pathogenic fungi and the like, and provide an important scientific basis for the research and development and creation of new pesticides.
Detailed Description
The following description will clearly and fully describe the technical solutions of the embodiments of the present invention, and it is apparent that the described embodiments are only some embodiments of the present invention, not all embodiments. All other embodiments, which can be made by those skilled in the art based on the embodiments of the invention without making any inventive effort, are intended to be within the scope of the invention.
The technical means used in the examples are conventional means well known to those skilled in the art unless otherwise indicated.
1. The invention discloses a phenothiazine compound containing an isopropanol substructure, which has a structural general formula shown as (I):
wherein R is 1 Is any one of hydrogen, optionally substituted or unsubstituted alkyl, optionally substituted or unsubstituted aryl, optionally substituted or unsubstituted benzyl, and optionally substituted or unsubstituted heteroaryl;
R 2 is hydrogen, optionally substituted or unsubstituted alkyl, optionally substituted or unsubstituted aryl, optionally substituted or unsubstitutedAny of substituted benzyl, optionally substituted or unsubstituted heteroaryl;
x is O, S or N.
Further, R 1 And R is 2 Each independently is any one of hydrogen, deuterium, optionally substituted or unsubstituted alkyl, optionally substituted or unsubstituted alkenyl, optionally substituted or unsubstituted alkynyl, optionally substituted or unsubstituted alkoxy, optionally substituted or unsubstituted cycloalkyl, optionally substituted or unsubstituted aryl, optionally substituted or unsubstituted heteroaryl.
Further, R 1 And R is 2 Independently hydrogen, optionally substituted or unsubstituted C 1 -C 16 Alkyl, optionally substituted or unsubstituted C 2 -C 6 Alkenyl, optionally substituted or unsubstituted C 2 -C 6 Alkynyl, optionally substituted or unsubstituted C 5 -C 10 Cycloalkyl, optionally substituted or unsubstituted C 5 -C 10 Aryl, optionally substituted or unsubstituted C 5 -C 10 Heteroaryl, optionally substituted or unsubstituted benzyl, methyl amino acid, optionally substituted or unsubstituted 1,2, 4-triazole thioether.
Further, R 1 And R is 2 Independently hydrogen, deuterium, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, neopentyl, ethenyl, propenyl, allyl, butenyl, pentenyl, hexenyl, propynyl, butynyl, pentynyl, hexynyl, methoxy, ethoxy, propoxy, butoxy, phenyl, chlorophenyl, bromophenyl, fluorophenyl, tolyl, aminophenyl, hydroxyphenyl, benzyl, o-fluorobenzyl, m-fluorobenzyl, p-fluorobenzyl, o-chlorobenzyl, m-chlorobenzyl, p-chlorobenzyl, o-bromobenzyl, m-bromobenzyl, p-bromobenzyl, naphthyl, phenanthryl, pyridyl, o-fluoropyridyl, m-fluoropyridyl, o-bromopyridyl, m-bromopyridyl, o-chloropyridyl, m-chloropyridyl, o-fluorothienyl, m-fluorothienyl, o-fluorotetrahydrofuranyl, m-fluorofuryl, m-fluorotetrahydrofuranyl, o-bromothienyl, m-bromothienyl, o-bromothienylA group selected from the group consisting of a methyl group, an m-bromofuranyl group, an o-bromotetrahydrofuranyl group, an m-bromotetrahydrofuranyl group, an o-chlorothiophene group, an m-chlorothiophene group, an o-chlorofuranyl group, an m-chlorofuranyl group, an o-chlorobenzyl group, an m-hydroxybenzyl group, a p-hydroxybenzyl group, an o-aminobenzyl group, an m-aminobenzyl group, an p-aminobenzyl group, an o-methylbenzyl group, an p-methylbenzyl group, an o-hydroxypyridine group, an m-hydroxypyridine group, a p-hydroxypyridine group, an o-aminothiophene group, an m-aminothiophene group, an o-hydroxyfuranyl group, an m-hydroxyfuranyl group, an o-hydroxytetrahydrofuranyl group, an m-hydroxytetrahydrofuranyl group, an o-methylfuranyl group, an m-methyltetrahydrofuranyl group, an o-furanmethylene group, an o-methylfuranyl group, an m-methyltetrahydrofuranyl group m-furanmethylene, o-tetrahydrofuranmethylene, m-tetrahydrofuranmethylene, glycine methyl ester, alanine methyl ester, valine methyl ester, leucine methyl ester, isoleucine methyl ester, methionine methyl ester, proline methyl ester, tryptophan methyl ester, serine methyl ester, tyrosine methyl ester, cysteine methyl ester, phenylalanine methyl ester, asparagine methyl ester, glutamine methyl ester, threonine methyl ester, aspartic acid methyl ester, glutamic acid methyl ester, lysine methyl ester, arginine methyl ester, histidine methyl ester, selenocysteine methyl ester, pyrrole lysine methyl ester, 4-amino-5-methyl-4H-1, 2, 4-triazole-3-thioether, 4-amino-5-isopropyl-4H-1, 2, 4-triazole-3-thioether, 4-amino-5-phenyl-4H-1, 2, 4-triazole-3-thioether, 4-amino-5- (pyridin-3-yl) -4H-1,2, 4-triazole-3-sulfide, 4-amino-5- (pyridin-2-yl) -4H-1,2, 4-triazole-3-sulfide, 4-amino-5- (fluorophenyl) -4H-1,2, 4-triazole-3-sulfide, and 4-amino-5- (phenoxymethyl) -4H-1,2, 4-triazole-3-sulfide.
2. The invention also discloses a preparation method of the phenothiazine compound containing the isopropanol substructure, and the reaction general formula is as follows:
wherein R is 1 、R 2 And X is the same as that disclosed in 1 above.
Further, preparation of intermediate 10- (ethylene oxide-2-methylene) -10H-phenothiazine
Phenothiazine (25 mmoL) was dissolved in 10 mM LDMF at 0-4deg.C. 37mmoL of NaH was added rapidly and stirring was continued for 10min. Subsequently, 30mmoL of epibromohydrin was added thereto. The reaction was continued for 6h at room temperature. Thereafter, 30mL of ethyl acetate was added to the system, and the mixture was washed with saturated ammonium chloride solution 2 times and water 3 times, respectively. Column chromatography gave the target intermediate in 55.3% yield.
To further illustrate the synthesis of the isopropanol substructure-containing phenothiazines of the present invention, the following are selectively synthesized.
3. The invention discloses a composition containing the compound or the compound prepared by the preparation method, and the composition is in the form of emulsifiable concentrate, wettable powder, granules, aqueous agent, suspending agent, ultra-low volume spray, soluble powder, microcapsule, smoke agent, aqueous emulsion or water dispersible granule. The composition can be prepared into bactericides, pesticides or herbicides by the compound and agricultural auxiliary agents.
4. The invention discloses application of the compound or the compound prepared by the preparation method or the composition in controlling agricultural diseases and insect pests.
Wherein the agricultural pest is a plant bacterial disease and/or a plant fungal disease and/or a plant viral disease.
Further, the bacterial diseases are rice bacterial leaf blight, cucumber bacterial leaf blight, konjak bacterial leaf blight, citrus canker, tobacco bacterial wilt, grape canker, tomato canker, kiwi fruit canker and apple canker; and/or the fungal diseases are cucumber gray mold, pepper blight, rape sclerotinia, wheat scab, potato late blight and rice sheath blight; and/or the viral diseases are tobacco mosaic disease, tomato mosaic disease, cucumber mosaic disease and rice dwarf disease.
5. The invention discloses a method for using the compound or the compound prepared by the preparation method or the composition, and the compound or the composition acts on harmful substances or living environments thereof or directly contacts plants.
The invention is further illustrated below in conjunction with specific examples.
EXAMPLE 1 preparation of the target compound 1- (methylamino) -3- (10H-phenothiazin-10-yl) isopropyl-2-ol
10- (ethylene oxide-2-methylene) -10H-phenothiazine (1 mmoL) and K 2 CO 3 The mixture of (0.5 mmoL) was dissolved in 5mL of isopropanol solution. Then, a methylamine solution (1.2 mmoL) was added to the mixture. After 7 hours of reaction at 45℃15ml of water was poured into the flask to obtain a suspension. The suspension was extracted 3 times with dichloromethane and the organic layer was dried under vacuum. Finally, the product was purified by column chromatography to give the target compound.
The following compounds were prepared in a similar manner to the above examples, substituting only the corresponding starting materials. The structure, nuclear magnetic resonance hydrogen spectrum and carbon spectrum data of the compound are shown in table 1, and the physicochemical properties are shown in table 2.
Nuclear magnetic resonance hydrogen spectrum and carbon spectrum data of the compounds of Table 1
TABLE 2 physicochemical Properties of the target Compounds
Example 2
1. The inhibition rate of the target compound on plant pathogenic bacteria is tested by adopting a turbidity method, and the test objects are rice bacterial blight bacteria (Xoo), citrus canker bacteria (Xac) and kiwi fruit canker bacteria (Psa). DMSO was dissolved in NB medium as a blank. Adding Xoo (the monoclonal of which is cultivated in an M210 solid culture medium in advance) into an NB culture medium, and carrying out shaking culture in a constant-temperature shaking table at 28 ℃ and 180rpm until the logarithmic phase is reserved; xac (Xac is cultured in M210 solid culture medium in advance) is put into NB culture medium, and is shake-cultured in a constant-temperature shaking table at 28 ℃ and 180rpm until logarithmic phase is reserved; psa (Psa was grown in advance in M210 solid medium) was placed in NB medium and shake-cultured in a thermostatic shaker at 28 ℃, 180rpm until log phase was ready for use. 5mL of toxic NB liquid culture medium with different concentrations (for example, 100,50 mug/mL) of the medicament (target compound) is prepared, and is added into a test tube, 40 mu L of NB liquid culture medium containing phytopathogenic bacteria is respectively added, and the mixture is oscillated in a constant temperature shaking table at 28-30 ℃ and 180rpm, wherein Xoo, xac and Psa are respectively cultured for 24-48 hours. Measuring OD of each toxic NB bacterial liquid on a spectrophotometer 595 Values, and additionally determining the OD of corresponding concentrations of toxic sterile NB liquid medium 595 Values.
Wherein, NB medium: water: 1L, glucose: 10g, protein span: 5g, beef extract: 3g, yeast powder: 1g.
M210 solid medium: water: 1L, glucose: 10g, protein span: 5g, beef extract: 3g, yeast powder: 1g, agar: 15g.
Corrected OD = bacteria-containing medium OD-sterile medium OD
Inhibition ratio = [ (corrected control culture medium bacterial liquid OD value-corrected toxic culture medium OD value)/corrected control culture medium bacterial liquid OD value ] ×100%
2. The inhibition rate of the target compound on Tobacco Mosaic Virus (TMV) was tested by a half-leaf spot method. Selecting greenhouse culture for more than 3 weeks, infecting upper leaves of host common smoke (Nicotiana tabacum) K326 plants by a TMV system, removing veins, and purifying. Therapeutic activity: selecting 5-6 leaf stage heart leaf cigarettes with consistent growth vigor, dipping virus juice by a row pen, rubbing and inoculating the heart leaf cigarettes on leaves scattered with silicon carbide, inoculating the whole leaf with the virus for 30min, and washing the whole leaf with clear water. After the leaves were dried, the right half She Tushi of the dose and the left half She Tushi of the corresponding dose of solvent were used as controls. Then culturing in a light incubator, controlling the temperature to be 23+/-1 ℃ in daytime (18 hours) and 18+/-1 ℃ at night (6 hours), and observing and recording the number of generated dead spots after light of 10000Lux for 2-3 days. 3 plants are treated with each medicament, and 3 to 4 leaves are treated for each plant. Protective activity: and selecting 5-6 leaf stage heart leaf cigarettes with consistent growth vigor, and using a writing brush to lightly apply the medicament on the right half She Tushi and the left half She Tushi of the corresponding dosage of the solvent as a control. Culturing in an illumination incubator, controlling the temperature to be 23+/-1 ℃ in daytime (18 hours) and 18+/-1 ℃ at night (6 hours), illuminating with 10000Lux for 24 hours, dipping virus juice by a gang pen, inoculating the virus juice on the leaves scattered with silicon carbide, and washing the leaves with clear water after 30 minutes of inoculation. And culturing in a light incubator continuously, observing and recording the number of generated dead spots after 2-3 d. 3 plants are treated with each medicament, and 3 to 4 leaves are treated for each plant.
Inhibition ratio (%) = [ (number of plaques in blank control-number of plaques in drug treatment)/number of plaques in blank control ] ×100%
3. In vitro test against pathogenic fungi the antibacterial activity of the synthesized target compounds against plant pathogenic fungi in PDA medium was tested using mycelium growth rate inhibition. Weighing a target compound to be measured by using a balance weight to prepare a mother solution with the concentration of 50 mug/mL, taking the mother solution with the corresponding volume under the corresponding concentration to a 2mL centrifuge tube, adding DMSO to trim to a final volume of 1mL, transferring to a 15mL sterilized centrifuge tube in a sterile operation table, adding 9mL Tween-20 to dissolve to 10mL, fully shaking and uniformly mixing, pouring into a culture medium, uniformly mixing, and uniformly split charging into 9 culture dishes for standby; in a sterile operation table, a bacterial colony which grows normally is made into a bacterial cake (bacterial cake diameter is 5 mm) by a sterile puncher (5 mm), the bacterial cake is reversely buckled in the center of a culture medium by a bacterial inoculating ring, the bacterial cake is cultured for 3 to 7 days at the temperature of 28 ℃, when the bacterial colony of a control group grows to 5.0 to 7.0cm in diameter, the bacterial colony is measured for 2 times by a straight ruler according to a cross method, and the diameter of the bacterial colony is calculated by an average value. The hypha growth inhibition ratio was determined according to the following formula. Azoxystrobin was tested as a control agent together.
PDA medium: potato, agar powder, glucose, magnesium sulfate, potassium dihydrogen phosphate, and vitamin B 1 Natural pH,121 ℃, and sterilizing for 30 min.
The calculation formula is as follows:
inhibition (%) = (C) 1 -C 2 )/(C 1 -0.5)×100％；
Wherein C is 1 Control colony diameter, DMSO-treated colony diameter/cm; c (C) 2 The diameter of the colony is treated, namely the diameter of the colony treated by adding medicine is/cm; 0.5 is the diameter/cm of the parent bacterial cake.
The present invention is described with the aid of examples, but the contents of examples are not limited thereto, and the experimental results of the target compounds are shown in tables 3, 4, 5 and 6.
TABLE 3 inhibitory Activity of Isopropanol substructure-containing phenothiazines against phytopathogenic bacteria
TABLE 4 EC of phenothiazines containing isopropanol substructure against phytopathogenic bacteria 50
TABLE 5 inhibition of TMV by phenothiazines containing the isopropanol substructure (500. Mu.g/mL)
Table 6 inhibition of three fungi by phenothiazines containing partial isopropanol substructure (25. Mu.g/mL)
As can be seen from tables 3 and 4, in vitro experiments, most of the target compounds were specific to plant pathogenic bacteria (such as bacterial leaf blight of riceBacteria, citrus canker and kiwifruit canker) exhibit good inhibitory activity. In particular, the compounds 11, 25, 26 and 32 have extremely excellent activity on rice bacterial blight bacteria, and EC 50 The values were all less than 1. Mu.g/mL.
Meanwhile, as can be seen from table 5, some of the target compounds also exhibited excellent inhibitory activity against TMV, with the protective activity of compounds 5, 9, 11, 34, 39, 42, 49, 50, 51, 52, 55, 56, 58, 62 and 67 being superior to that of the positive control drug ningnanmycin. The compound has a great research prospect and can be used for preparing the microbial pesticide for resisting plant pathogenic bacteria.
The above embodiments are only illustrative of the preferred embodiments of the present invention and are not intended to limit the scope of the present invention, and various modifications and improvements made by those skilled in the art to the technical solutions of the present invention should fall within the protection scope defined by the claims of the present invention without departing from the design spirit of the present invention.
Claims (10)
1. A phenothiazine compound containing an isopropanol substructure is characterized in that: the structural general formula is shown as (I):
wherein R is 1 Is any one of hydrogen, optionally substituted or unsubstituted alkyl, optionally substituted or unsubstituted aryl, optionally substituted or unsubstituted benzyl, and optionally substituted or unsubstituted heteroaryl;
R 2 is any one of hydrogen, optionally substituted or unsubstituted alkyl, optionally substituted or unsubstituted aryl, optionally substituted or unsubstituted benzyl, and optionally substituted or unsubstituted heteroaryl;
x is O, S or N.
2. The phenothiazine compound having an isopropanol substructure according to claim 1, wherein: r is R 1 And R is 2 Each independently is any one of hydrogen, deuterium, optionally substituted or unsubstituted alkyl, optionally substituted or unsubstituted alkenyl, optionally substituted or unsubstituted alkynyl, optionally substituted or unsubstituted alkoxy, optionally substituted or unsubstituted cycloalkyl, optionally substituted or unsubstituted aryl, optionally substituted or unsubstituted heteroaryl.
3. The phenothiazine compound having an isopropanol substructure according to claim 2, wherein: r is R 1 And R is 2 Independently hydrogen, optionally substituted or unsubstituted C 1 -C 16 Alkyl, optionally substituted or unsubstituted C 2 -C 6 Alkenyl, optionally substituted or unsubstituted C 2 -C 6 Alkynyl, optionally substituted or unsubstituted C 5 -C 10 Cycloalkyl, optionally substituted or unsubstituted C 5 -C 10 Aryl, optionally substituted or unsubstituted C 5 -C 10 Heteroaryl, optionally substituted or unsubstituted benzyl, methyl amino acid, optionally substituted or unsubstituted 1,2, 4-triazole thioether.
4. A phenothiazine compound according to claim 3 comprising an isopropanol substructure, characterized in that: r is R 1 And R is 2 Independently hydrogen, deuterium, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, neopentyl, ethenyl, propenyl, allyl, butenyl, pentenyl, hexenyl, propynyl, butynyl, pentynyl, hexynyl, methoxy, ethoxy, propoxy, butoxy, phenyl, chlorophenyl, bromophenyl, fluorophenyl, tolyl, aminophenyl, hydroxyphenyl, benzyl, o-fluorobenzyl, m-fluorobenzyl, p-fluorobenzyl, o-chlorobenzyl, m-chlorobenzyl, p-chlorobenzyl, o-bromobenzyl, m-bromobenzyl, p-bromobenzyl, naphthyl, phenanthryl, pyridyl, o-fluoropyridyl, m-fluoropyridyl, o-bromopyridyl, m-bromopyridyl, o-chloropyridyl, m-chloropyridyl, o-fluorothienyl, m-fluorothienyl, o-fluorotetrahydrofuranyl, m-fluorofuryl, m-fluorotetrahydrofuranylAn o-bromothienyl, m-bromothienyl, o-bromofuryl, m-bromofuryl, o-bromotetrahydrofuranyl, m-bromotetrahydrofuranyl, o-chlorothioanyl, m-chlorothiothienyl, o-chlorofuryl, m-chlorofuryl, o-chlorotetrahydrofuranyl, m-chlorotetrahydrofuranyl, o-hydroxybenzyl, m-hydroxybenzyl, p-hydroxybenzyl, o-aminobenzyl, p-aminobenzyl, o-methylbenzyl, m-methylbenzyl, p-methylbenzyl, o-hydroxypyridine, m-hydroxypyridine, p-hydroxypyridine, o-aminothiophene, m-aminothiophene, o-hydroxyfuryl, m-hydroxyfuryl, o-hydroxytetrahydrofuranyl, m-hydroxytetrahydrofuranyl, o-methylfuryl, m-methylfuryl, o-methyltetrahydrofuranyl, m-methyltetrahydrofuranyl O-furanmethylene, m-furanmethylene, O-tetrahydrofuranmethylene, m-tetrahydrofuranmethylene, glycine methyl, alanine methyl, valine methyl, leucine methyl, isoleucine methyl, methionine methyl, proline methyl, tryptophan methyl, serine methyl, tyrosine methyl, cysteine methyl, phenylalanine methyl, asparagine methyl, glutamine methyl, threonine methyl, aspartic acid methyl, glutamic acid methyl, lysine methyl, arginine methyl, histidine methyl, selenium cysteine methyl, pyrrole lysine methyl, 4-amino-5-methyl-4H-1, 2, 4-triazole-3-thioether, 4-amino-5-isopropyl-4H-1, 2, 4-triazole-3-thioether, 4-amino-5-phenyl-4H-1, 2, 4-triazole-3-thioether, 4-amino-5- (pyridin-3-yl) -4H-1,2, 4-triazole-3-sulfide, 4-amino-5- (pyridin-2-yl) -4H-1,2, 4-triazole-3-sulfide, 4-amino-5- (fluorophenyl) -4H-1,2, 4-triazole-3-sulfide, and 4-amino-5- (phenoxymethyl) -4H-1,2, 4-triazole-3-sulfide.
5. The method for producing a phenothiazine compound having an isopropanol substructure according to any one of claims 1 to 4, wherein: the reaction general formula is:
6. a composition comprising a compound according to any one of claims 1 to 4 or a compound produced by the production method according to claim 5, characterized in that: the formulation of the composition is emulsifiable concentrate, wettable powder, granules, water aqua, suspending agent, ultra-low volume spray, soluble powder, microcapsule, smoke agent, aqueous emulsion or water dispersible granule.
7. Use of a compound according to any one of claims 1 to 4 or a compound prepared by a method according to claim 5 or a composition according to claim 6 for controlling agricultural pests.
8. The use according to claim 7, characterized in that: the agricultural pest is a plant bacterial disease and/or a plant fungal disease and/or a plant viral disease.
9. The use according to claim 8, characterized in that: the bacterial diseases are rice bacterial leaf blight, cucumber bacterial leaf blight, konjak bacterial leaf blight, citrus canker, tobacco bacterial wilt, grape canker, tomato canker, kiwi fruit canker and apple canker; and/or the fungal diseases are cucumber gray mold, pepper blight, rape sclerotinia, wheat scab, potato late blight and rice sheath blight; and/or the viral diseases are tobacco mosaic disease, tomato mosaic disease, cucumber mosaic disease and rice dwarf disease.
10. A method of using a compound according to any one of claims 1 to 4 or a compound prepared by a method of preparation according to claim 5 or a composition according to claim 6, characterized in that: the compound or composition is applied to a pest or an environment in which it is living, or is directly contacted with plants.
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| US20010012857A1 (en) * | 1996-05-31 | 2001-08-09 | Ognyanov Vassil Iliya | Pharmaceutical for treatment of neurological and neuropsychiatric disorders |
| CN109627205A (en) * | 2019-01-11 | 2019-04-16 | 贵州大学 | The preparation method and applications of a kind of carbazyl Isopropanolamine derivatives |
| CN113264903A (en) * | 2021-05-27 | 2021-08-17 | 郑州大学 | Phenothiazine compound and preparation method and application thereof |
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| US20010012857A1 (en) * | 1996-05-31 | 2001-08-09 | Ognyanov Vassil Iliya | Pharmaceutical for treatment of neurological and neuropsychiatric disorders |
| CN109627205A (en) * | 2019-01-11 | 2019-04-16 | 贵州大学 | The preparation method and applications of a kind of carbazyl Isopropanolamine derivatives |
| CN113264903A (en) * | 2021-05-27 | 2021-08-17 | 郑州大学 | Phenothiazine compound and preparation method and application thereof |
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