CN110734411A - 一种含有酰胺类化合物的药物组合物及其应用 - Google Patents
一种含有酰胺类化合物的药物组合物及其应用 Download PDFInfo
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- CN110734411A CN110734411A CN201910656365.2A CN201910656365A CN110734411A CN 110734411 A CN110734411 A CN 110734411A CN 201910656365 A CN201910656365 A CN 201910656365A CN 110734411 A CN110734411 A CN 110734411A
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- amide compound
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- -1 amide compounds Chemical class 0.000 title claims abstract description 124
- 239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 45
- 150000001875 compounds Chemical class 0.000 claims abstract description 121
- 239000004480 active ingredient Substances 0.000 claims abstract description 93
- 201000010099 disease Diseases 0.000 claims abstract description 50
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 50
- 239000000575 pesticide Substances 0.000 claims abstract description 18
- 230000000844 anti-bacterial effect Effects 0.000 claims abstract description 17
- 239000003899 bactericide agent Substances 0.000 claims abstract description 13
- 239000002917 insecticide Substances 0.000 claims abstract description 8
- 241000238631 Hexapoda Species 0.000 claims abstract description 7
- 241000607479 Yersinia pestis Species 0.000 claims abstract description 7
- 230000000895 acaricidal effect Effects 0.000 claims abstract description 7
- 239000000642 acaricide Substances 0.000 claims abstract description 7
- 238000002360 preparation method Methods 0.000 claims description 56
- 238000000034 method Methods 0.000 claims description 52
- 239000004495 emulsifiable concentrate Substances 0.000 claims description 19
- 239000005828 Pyrimethanil Substances 0.000 claims description 18
- 239000005857 Trifloxystrobin Substances 0.000 claims description 18
- ZLIBICFPKPWGIZ-UHFFFAOYSA-N pyrimethanil Chemical compound CC1=CC(C)=NC(NC=2C=CC=CC=2)=N1 ZLIBICFPKPWGIZ-UHFFFAOYSA-N 0.000 claims description 18
- 239000000243 solution Substances 0.000 claims description 18
- 239000005730 Azoxystrobin Substances 0.000 claims description 17
- 239000005825 Prothioconazole Substances 0.000 claims description 17
- MNHVNIJQQRJYDH-UHFFFAOYSA-N 2-[2-(1-chlorocyclopropyl)-3-(2-chlorophenyl)-2-hydroxypropyl]-1,2-dihydro-1,2,4-triazole-3-thione Chemical compound N1=CNC(=S)N1CC(C1(Cl)CC1)(O)CC1=CC=CC=C1Cl MNHVNIJQQRJYDH-UHFFFAOYSA-N 0.000 claims description 16
- ONCZDRURRATYFI-TVJDWZFNSA-N trifloxystrobin Chemical compound CO\N=C(\C(=O)OC)C1=CC=CC=C1CO\N=C(/C)C1=CC=CC(C(F)(F)F)=C1 ONCZDRURRATYFI-TVJDWZFNSA-N 0.000 claims description 16
- 239000005869 Pyraclostrobin Substances 0.000 claims description 15
- 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 claims description 15
- 239000005747 Chlorothalonil Substances 0.000 claims description 14
- HZRSNVGNWUDEFX-UHFFFAOYSA-N pyraclostrobin Chemical compound COC(=O)N(OC)C1=CC=CC=C1COC1=NN(C=2C=CC(Cl)=CC=2)C=C1 HZRSNVGNWUDEFX-UHFFFAOYSA-N 0.000 claims description 14
- PXMNMQRDXWABCY-UHFFFAOYSA-N 1-(4-chlorophenyl)-4,4-dimethyl-3-(1H-1,2,4-triazol-1-ylmethyl)pentan-3-ol Chemical compound C1=NC=NN1CC(O)(C(C)(C)C)CCC1=CC=C(Cl)C=C1 PXMNMQRDXWABCY-UHFFFAOYSA-N 0.000 claims description 13
- 239000005839 Tebuconazole Substances 0.000 claims description 13
- 239000005842 Thiophanate-methyl Substances 0.000 claims description 13
- CRQQGFGUEAVUIL-UHFFFAOYSA-N chlorothalonil Chemical compound ClC1=C(Cl)C(C#N)=C(Cl)C(C#N)=C1Cl CRQQGFGUEAVUIL-UHFFFAOYSA-N 0.000 claims description 13
- 239000000725 suspension Substances 0.000 claims description 13
- WOSNCVAPUOFXEH-UHFFFAOYSA-N thifluzamide Chemical compound S1C(C)=NC(C(F)(F)F)=C1C(=O)NC1=C(Br)C=C(OC(F)(F)F)C=C1Br WOSNCVAPUOFXEH-UHFFFAOYSA-N 0.000 claims description 13
- 229930195482 Validamycin Natural products 0.000 claims description 12
- 150000001408 amides Chemical class 0.000 claims description 12
- QGHREAKMXXNCOA-UHFFFAOYSA-N thiophanate-methyl Chemical compound COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC QGHREAKMXXNCOA-UHFFFAOYSA-N 0.000 claims description 12
- 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 claims description 12
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 11
- 239000005740 Boscalid Substances 0.000 claims description 11
- 239000005941 Thiamethoxam Substances 0.000 claims description 11
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- WYEMLYFITZORAB-UHFFFAOYSA-N boscalid Chemical compound C1=CC(Cl)=CC=C1C1=CC=CC=C1NC(=O)C1=CC=CN=C1Cl WYEMLYFITZORAB-UHFFFAOYSA-N 0.000 claims description 11
- NWWZPOKUUAIXIW-FLIBITNWSA-N thiamethoxam Chemical compound [O-][N+](=O)\N=C/1N(C)COCN\1CC1=CN=C(Cl)S1 NWWZPOKUUAIXIW-FLIBITNWSA-N 0.000 claims description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- 239000001257 hydrogen Substances 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 239000005760 Difenoconazole Substances 0.000 claims description 8
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- BQYJATMQXGBDHF-UHFFFAOYSA-N difenoconazole Chemical compound O1C(C)COC1(C=1C(=CC(OC=2C=CC(Cl)=CC=2)=CC=1)Cl)CN1N=CN=C1 BQYJATMQXGBDHF-UHFFFAOYSA-N 0.000 claims description 8
- SXSGXWCSHSVPGB-UHFFFAOYSA-N fluxapyroxad Chemical compound FC(F)C1=NN(C)C=C1C(=O)NC1=CC=CC=C1C1=CC(F)=C(F)C(F)=C1 SXSGXWCSHSVPGB-UHFFFAOYSA-N 0.000 claims description 8
- QHGVXILFMXYDRS-UHFFFAOYSA-N pyraclofos Chemical compound C1=C(OP(=O)(OCC)SCCC)C=NN1C1=CC=C(Cl)C=C1 QHGVXILFMXYDRS-UHFFFAOYSA-N 0.000 claims description 8
- ZMYFCFLJBGAQRS-IRXDYDNUSA-N (2R,3S)-epoxiconazole Chemical compound C1=CC(F)=CC=C1[C@@]1(CN2N=CN=C2)[C@H](C=2C(=CC=CC=2)Cl)O1 ZMYFCFLJBGAQRS-IRXDYDNUSA-N 0.000 claims description 7
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 7
- STMIIPIFODONDC-UHFFFAOYSA-N 2-(2,4-dichlorophenyl)-1-(1H-1,2,4-triazol-1-yl)hexan-2-ol Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(O)(CCCC)CN1C=NC=N1 STMIIPIFODONDC-UHFFFAOYSA-N 0.000 claims description 7
- HZJKXKUJVSEEFU-UHFFFAOYSA-N 2-(4-chlorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)hexanenitrile Chemical compound C=1C=C(Cl)C=CC=1C(CCCC)(C#N)CN1C=NC=N1 HZJKXKUJVSEEFU-UHFFFAOYSA-N 0.000 claims description 7
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- 239000000839 emulsion Substances 0.000 claims description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
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- YWTYJOPNNQFBPC-UHFFFAOYSA-N imidacloprid Chemical compound [O-][N+](=O)\N=C1/NCCN1CC1=CC=C(Cl)N=C1 YWTYJOPNNQFBPC-UHFFFAOYSA-N 0.000 claims description 7
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 7
- 239000000843 powder Substances 0.000 claims description 7
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 6
- ZOCSXAVNDGMNBV-UHFFFAOYSA-N 5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-[(trifluoromethyl)sulfinyl]-1H-pyrazole-3-carbonitrile Chemical compound NC1=C(S(=O)C(F)(F)F)C(C#N)=NN1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl ZOCSXAVNDGMNBV-UHFFFAOYSA-N 0.000 claims description 6
- 239000005899 Fipronil Substances 0.000 claims description 6
- 239000005818 Picoxystrobin Substances 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 229940013764 fipronil Drugs 0.000 claims description 6
- 239000008187 granular material Substances 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 150000002367 halogens Chemical class 0.000 claims description 6
- UFHLMYOGRXOCSL-UHFFFAOYSA-N isoprothiolane Chemical compound CC(C)OC(=O)C(C(=O)OC(C)C)=C1SCCS1 UFHLMYOGRXOCSL-UHFFFAOYSA-N 0.000 claims description 6
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 6
- IBSNKSODLGJUMQ-SDNWHVSQSA-N picoxystrobin Chemical compound CO\C=C(\C(=O)OC)C1=CC=CC=C1COC1=CC=CC(C(F)(F)F)=N1 IBSNKSODLGJUMQ-SDNWHVSQSA-N 0.000 claims description 6
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 5
- PGOOBECODWQEAB-UHFFFAOYSA-N (E)-clothianidin Chemical compound [O-][N+](=O)\N=C(/NC)NCC1=CN=C(Cl)S1 PGOOBECODWQEAB-UHFFFAOYSA-N 0.000 claims description 5
- TWFZGCMQGLPBSX-UHFFFAOYSA-N Carbendazim Natural products C1=CC=C2NC(NC(=O)OC)=NC2=C1 TWFZGCMQGLPBSX-UHFFFAOYSA-N 0.000 claims description 5
- 239000005888 Clothianidin Substances 0.000 claims description 5
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- JNPZQRQPIHJYNM-UHFFFAOYSA-N carbendazim Chemical compound C1=C[CH]C2=NC(NC(=O)OC)=NC2=C1 JNPZQRQPIHJYNM-UHFFFAOYSA-N 0.000 claims description 5
- 239000011248 coating agent Substances 0.000 claims description 5
- 238000000576 coating method Methods 0.000 claims description 5
- KAATUXNTWXVJKI-UHFFFAOYSA-N cypermethrin Chemical compound CC1(C)C(C=C(Cl)Cl)C1C(=O)OC(C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 KAATUXNTWXVJKI-UHFFFAOYSA-N 0.000 claims description 5
- YKBZOVFACRVRJN-UHFFFAOYSA-N dinotefuran Chemical compound [O-][N+](=O)\N=C(/NC)NCC1CCOC1 YKBZOVFACRVRJN-UHFFFAOYSA-N 0.000 claims description 5
- MUJOIMFVNIBMKC-UHFFFAOYSA-N fludioxonil Chemical compound C=12OC(F)(F)OC2=CC=CC=1C1=CNC=C1C#N MUJOIMFVNIBMKC-UHFFFAOYSA-N 0.000 claims description 5
- 150000002431 hydrogen Chemical class 0.000 claims description 5
- 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 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- TVLSRXXIMLFWEO-UHFFFAOYSA-N prochloraz Chemical compound C1=CN=CN1C(=O)N(CCC)CCOC1=C(Cl)C=C(Cl)C=C1Cl TVLSRXXIMLFWEO-UHFFFAOYSA-N 0.000 claims description 5
- 125000004738 (C1-C6) alkyl sulfinyl group Chemical group 0.000 claims description 4
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- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 4
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims description 4
- WURBVZBTWMNKQT-UHFFFAOYSA-N 1-(4-chlorophenoxy)-3,3-dimethyl-1-(1,2,4-triazol-1-yl)butan-2-one Chemical compound C1=NC=NN1C(C(=O)C(C)(C)C)OC1=CC=C(Cl)C=C1 WURBVZBTWMNKQT-UHFFFAOYSA-N 0.000 claims description 4
- IBSREHMXUMOFBB-JFUDTMANSA-N 5u8924t11h Chemical compound O1[C@@H](C)[C@H](O)[C@@H](OC)C[C@@H]1O[C@@H]1[C@@H](OC)C[C@H](O[C@@H]2C(=C/C[C@@H]3C[C@@H](C[C@@]4(O3)C=C[C@H](C)[C@@H](C(C)C)O4)OC(=O)[C@@H]3C=C(C)[C@@H](O)[C@H]4OC\C([C@@]34O)=C/C=C/[C@@H]2C)/C)O[C@H]1C.C1=C[C@H](C)[C@@H]([C@@H](C)CC)O[C@]11O[C@H](C\C=C(C)\[C@@H](O[C@@H]2O[C@@H](C)[C@H](O[C@@H]3O[C@@H](C)[C@H](O)[C@@H](OC)C3)[C@@H](OC)C2)[C@@H](C)\C=C\C=C/2[C@]3([C@H](C(=O)O4)C=C(C)[C@@H](O)[C@H]3OC\2)O)C[C@H]4C1 IBSREHMXUMOFBB-JFUDTMANSA-N 0.000 claims description 4
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- ZQEIXNIJLIKNTD-UHFFFAOYSA-N methyl N-(2,6-dimethylphenyl)-N-(methoxyacetyl)alaninate Chemical compound COCC(=O)N(C(C)C(=O)OC)C1=C(C)C=CC=C1C ZQEIXNIJLIKNTD-UHFFFAOYSA-N 0.000 claims description 4
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- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/587—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with aliphatic hydrocarbon radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms, said aliphatic radicals being substituted in the alpha-position to the ring by a hetero atom, e.g. with m >= 0, Z being a singly or a doubly bound hetero atom
-
- 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
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/34—Nitriles
-
- 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
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/44—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a nitrogen atom attached to the same carbon skeleton by a single or double bond, this nitrogen atom not being a member of a derivative or of a thio analogue of a carboxylic group, e.g. amino-carboxylic acids
- A01N37/50—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a nitrogen atom attached to the same carbon skeleton by a single or double bond, this nitrogen atom not being a member of a derivative or of a thio analogue of a carboxylic group, e.g. amino-carboxylic acids the nitrogen atom being doubly bound to the carbon skeleton
-
- 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
-
- 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
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/36—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom five-membered rings
-
- 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
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
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Abstract
本发明提供了一种含有酰胺类化合物的药物组合物及其应用,所述药物组合物包括有效成分A和有效成分B,所述有效成分A为具有式I所示结构的酰胺类化合物,所述有效成分B包括其他杀菌剂、杀虫剂或杀螨剂中任意一种或两种的组合;本发明中有效成分A和有效成分B具有协同增效作用,药剂使用量较单一活性成分杀菌剂大大降低,防治效果显著提高,扩大了防治谱,可应用于蔬菜、果树、花卉、禾谷、油料、糖料等作物及园艺、林业上的多种病虫害,延缓药剂抗药性产生,可以有效防止或减缓病原菌对一类作用机理的化合物产生抗药性。
Description
技术领域
本发明属于杀菌杀虫剂技术领域,涉及一种含有酰胺类化合物的药物组合物及其应用。
背景技术
植物的生长严重受到植物病虫害的影响,导致农作物减产,降低农产品商品性,造成巨大社会危害和经济损失,因此针对植物病虫害开发有效的植保产品具有重要的意义。
现有技术中,CN1226244A公开了一些酰胺类化合物具有杀菌效果的抗菌剂,另一方面,各种不同结构类型的杀菌剂广泛用于各种不同的农作物,但单个结构类型杀菌剂的杀菌谱有限。同时,随着农药的不断使用,病害会对一些现有农药产品产生抗药性,使得现有农药品种单独使用的杀菌活性不总是能满足许多农业实践的需要。
杀菌剂组合物对提高防效、扩大防治谱、减少用量和延缓抗性产生具有重要的作用。因此,在本领域中,期望开发出更加高效的组合物以满足农业、园艺以及林木业需求。
发明内容
针对现有技术存在的问题,本发明的目的在于提供一种含有酰胺类化合物的药物组合物及其应用。
为达此目的,本发明采用以下技术方案:
一方面,本发明提供一种含有酰胺类化合物的药物组合物,所述药物组合物包括有效成分A和有效成分B,所述有效成分A为具有式I所示结构的酰胺类化合物,所述有效成分B包括其他杀菌剂、杀虫剂或杀螨剂中任意一种或两种的组合;
X选自C2-C12烷基、C1-C12烷氧基、C1-C12卤代烷氧基、C2-C12烯基、C2-C12卤代烯基、C2-C12炔基、C2-C12卤代炔基、C3-C8环烷基、C3-C8卤代环烷基、C1-C12烷基亚磺酰基、C1-C12卤代烷基亚磺酰基、C1-C12烷基磺酰基或C1-C12卤代烷基磺酰基;Y选自C1-C6烷基、C1-C6卤代烷基、C1-C6烷氧基、C1-C6卤代烷氧基、C2-C4烯基、C2-C4卤代烯基、C2-C4炔基、C2-C4卤代炔基、C3-C8环烷基、C3-C8卤代环烷基、C1-C6烷基亚磺酰基、C1-C6卤代烷基亚磺酰基、C1-C6烷基磺酰基或C1-C6卤代烷基磺酰基;R1选自氢、卤素、氰基、硝基、取代或未取代的烷基、取代或未取代的烷氧基、取代或未取代的烯基、取代或未取代的炔基、取代或未取代的环烷基、取代或未取代的烷基亚磺酰基、取代或未取代的烷基磺酰基;W表示氧原子或硫原子,m为0-4的整数(例如0、1、2、3或4)。
优选地,R1选自氢、卤素、氰基、硝基、C1-C6烷基、C1-C6卤代烷基、C1-C6烷氧基、C1-C6卤代烷氧基、C2-C4烯基、C2-C4卤代烯基、C2-C4炔基、C2-C4卤代炔基、C3-C8环烷基、C3-C8卤代环烷基、C1-C6烷基亚磺酰基、C1-C6卤代烷基亚磺酰基、C1-C6烷基磺酰基或C1-C6卤代烷基磺酰基。
优选地,R2选自C1-C6烷基或C1-C6卤代烷基。
在本发明中,所述卤素为氟、氯、溴或碘。
作为本发明的优选技术方案,所述酰胺类化合物为具有通式I的如下表1所示化合物中的任意一种或至少两种的组合:
表1
其中Me为甲基、Et为乙基,4-F、4-Cl、4-Me和5-CF3中的数字代表原子或基团在苯环上的位置。
进一步优选地,在式I中:Q选自R2选自二氟甲基或三氟甲基;X选自C2-C12烷基;Y选自C1-C6烷基;R1选自氢(当R1选自氢时表示苯环上并没有R1所代表的其他取代基,因此此时m的限定并无意义,因此无需对m进行额外限定),W表示氧原子。
最优选地,所述酰胺类化合物为如下化合物中的任意一种:
在本发明中,所述烷基是指直链或支链形式,例如甲基、乙基、正丙基、异丙基、正丁基、异丁基、仲丁基、特丁基、正戊基、异戊基、正己基等基团。卤代烷基是指烷基被一个或多个卤原子取代的基团。烷氧基是指烷基末端连有氧原子的基团,例如甲氧基、乙氧基、正丙氧基、异丙氧基、特丁氧基等。卤代烷氧基是指烷氧基被一个或多个卤原子取代的基团。卤素为F、Cl、Br或I。
本发明所用术语“C1-C6烷基”是指具有1至6个碳原子的直链或支链烷基,非限制性地包括甲基、乙基、正丙基、异丙基、正丁基、异丁基、仲丁基、特丁基、正戊基、异戊基、正己基等。术语“C1-C6烷氧基”是指具有1至6个碳原子的直链或支链烷氧基,非限制性地包括甲氧基、乙氧基、正丙氧基、异丙氧基和特丁氧基等。术语“C1-C12烷氧基”具有类似的含义。
本发明所用术语“C3-C8环烷基”是指在环上具有3至8个碳原子的环状烷基,非限制性地包括环丙基、环丁基、环戊基、环己基、环庚基、环辛基等。
在本发明中,所述特定基团之前的C2-C12、C1-C6、C3-C8等表示基团中所含碳原子个数,例如C2-C12表示碳原子数可以为2、3、4、5、6、7、8、9、10、11或12的基团,C1-C6表示碳原子数可以为1、2、3、4、5或6的基团,C3-C8表示碳原子数可以为3、4、5、6、7或8的基团,C2-C4表示碳原子数可以为2、3或4的基团等等,以此类推。
在本发明中,式I所示结构的酰胺类化合物通过如下制备方法制备得到:
将式II所示化合物与式III所示化合物反应得到式I所示酰胺类化合物,反应式如下:
其中LG表示易离去基团,优选氯原子、溴原子、烷氧基或酰氧基;Q、X、Y、R1、W和m的限定如上文所述,在此不再赘述。
优选地,所述式II所示化合物与式III所示化合物的摩尔比为0.5-2:1,例如0.5:1、0.8:1、1:1、1.2:1、1.5:1、1.8:1或2:1。
优选地,所述反应在碱性物质存在下进行,所述碱性物质为有机碱和/或无机碱。
优选地,所述有机碱为三乙胺、N,N-二异丙基乙胺、N,N-二甲基苯胺、吡啶、甲醇钠、乙醇钠、叔丁醇钠或叔丁醇钾中的任意一种或至少两种的组合。
优选地,所述无机碱为氢氧化钠、氢氧化钾、碳酸钠、碳酸钾或氢化钠中的任意一种或至少两种的组合。
在本发明中,所述碱性物质的使用量为相对于式III所示反应原料为催化量或化学计量或过量。
优选地,所述反应的溶剂为二氯甲烷、氯仿、乙酸乙酯、甲苯、乙腈、四氢呋喃、二氧六环、乙醇、甲醇、N,N-二甲基甲酰胺或二甲基亚砜等中的任意一种或至少两种的组合。
优选地,所述反应的温度为大于等于室温小于等于反应溶剂的沸点,例如20℃、25℃、30℃、35℃、40℃、45℃、50℃、60℃、70℃、75℃、80℃、85℃、90℃等,或者在溶剂沸点即回流状态下进行反应。
优选地,所述反应的时间为0.5-48小时,例如0.5小时、1小时、3小时、5小时、8小时、10小时、12小时、15小时、18小时、20小时、23小时、25小时、28小时、30小时、33小时、35小时、38小时、40小时、44小时或48小时。
优选地,式III所示化合物通过以下方法制备得到:式IV所示化合物在还原剂存在下还原得到式III所示化合物,反应式如下:
其中X、Y、R1、和m的限定如上文所述,在此不再赘述。
优选地,在式III所示化合物的制备中,所述还原剂为氢气、水合肼、铁粉、锌粉、氯化亚锡或连二亚硫酸钠中的任意一种或至少两种的组合。
优选地,在式III所示化合物的制备中,所述反应在催化剂存在下进行,所述催化剂优选钯碳、二氧化钯、兰尼镍、三氯化铁或碱式氧化铁中的任意一种或至少两种的组合。
优选地,在式III所示化合物的制备中,所述反应的溶剂为二氯甲烷、氯仿、乙酸乙酯、甲苯、乙腈、四氢呋喃、二氧六环、乙醇、甲醇、N,N-二甲基甲酰胺、饱和氯化铵水溶液、乙酸、盐酸、水或二甲基亚砜中的任意一种或至少两种的组合。
优选地,在式III所示化合物的制备中,所述反应的温度为大于等于0℃小于等于反应溶剂的沸点,例如0℃、3℃、5℃、8℃、10℃、15℃、20℃、25℃、30℃、35℃、40℃、45℃、50℃、60℃、70℃、75℃、80℃、85℃、90℃等,或者在溶剂沸点即回流状态下进行反应。
优选地,在式III所示化合物的制备中,所述反应的时间为0.5-48小时,例如0.5小时、1小时、3小时、5小时、8小时、10小时、12小时、15小时、18小时、20小时、23小时、25小时、28小时、30小时、33小时、35小时、38小时、40小时、44小时或48小时。
优选地,式IV所示化合物通过以下方法制备得到:式V所示化合物与式VI所示化合物反应得到式IV所示化合物,反应式如下:
其中L为易于发生亲核取代的基团,优选氟或氯,此外,X、Y、R1和m的限定如上文所述,在此不再赘述。
优选地,式V所示化合物与式VI所示化合物的摩尔比为1-3:1,例如1:1、1.2:1、1.5:1、1.8:1、2:1、2.3:1、2.5:1、2.8:1或3:1。
优选地,在式IV所示化合物的制备中,所述反应在碱性物质存在下进行,所述碱性物质为有机碱和/或无机碱。
优选地,所述有机碱为三乙胺、N,N-二甲基苯胺、吡啶、甲醇钠、乙醇钠、叔丁醇钠或叔丁醇钾中的任意一种或至少两种的组合。
优选地,所述无机碱为氢氧化钠、氢氧化钾、碳酸钠、碳酸钾或氢化钠中的任意一种或至少两种的组合。
优选地,在式IV所示化合物的制备中,所述反应的溶剂为二氯甲烷、氯仿、丙酮、甲苯、乙腈、四氢呋喃、二氧六环、甲醇、乙醇、N,N-二甲基甲酰胺、二甲基亚砜或六甲基磷酰三胺中的任意一种或至少两种的组合。
优选地,在式IV所示化合物的制备中,所述反应的温度为大于等于室温小于等于反应溶剂的沸点,例如20℃、25℃、30℃、35℃、40℃、45℃、50℃、60℃、70℃、75℃、80℃、85℃、90℃等,或者在溶剂沸点即回流状态下进行反应。
优选地,在式IV所示化合物的制备中,所述反应的时间为0.5-48小时,例如0.5小时、1小时、3小时、5小时、8小时、10小时、12小时、15小时、18小时、20小时、23小时、25小时、28小时、30小时、33小时、35小时、38小时、40小时、44小时或48小时。
在本发明中,所用原料式VI化合物中部分化合物为市售试剂,部分化合物可以参照文献合成,如J.AM.CHEM.SOC.2006,128,1840-1846。
优选地,所述有效成分B选自目前已有的杀菌剂、杀虫剂、杀螨剂中的任意一种或至少两种的组合。
优选地,所述杀菌剂选自环丙唑醇、丙硫菌唑、苯醚甲环唑、氟环唑、烯唑醇、腈苯唑、氟硅唑、粉唑醇、戊唑醇、己唑醇、腈菌唑、戊菌唑、丙环唑、四氟醚唑、三唑醇、联苯三唑醇、三唑酮、嘧菌酯、醚菌酯、肟菌酯、啶氧菌酯、吡唑醚菌酯、氟嘧菌酯、肟醚菌胺、丁香菌酯、烯肟菌酯、烯肟菌胺、唑菌酯、氟唑菌酰胺、联苯吡菌胺、苯丙烯氟菌唑、氟唑菌酰羟胺、甲霜灵、精甲霜灵、氟酰胺、噻呋酰胺、缬霉威、噻唑菌胺、双炔酰菌胺、啶酰菌胺、氟吡菌胺、稻瘟酰胺、氟吡菌酰胺、萎锈灵、噻菌灵、抑霉唑、咪鲜胺、稻瘟酯、腈霜唑、氟菌唑、腐霉利、异菌脲、乙烯菌核利、克菌丹、菌核净、霜霉威盐酸盐、乙霉威、多菌灵、苯菌灵、甲基硫菌灵、井冈霉素、中生菌素、硫酸链霉素、多抗霉素、春雷霉素、梧宁霉素、噁霉灵、噁霜灵、烯酰吗啉、氟吗啉、十三吗啉、嘧菌环胺、嘧霉胺、乙嘧酚、二氰蒽醌、代森联、福美双、代森锌、代森锰、代森锰锌、丙森锌、敌瘟磷、三乙膦酸铝、百菌清、稻瘟灵、三环唑、五氯硝基苯、噁唑菌酮、霜脲腈、咯菌腈、敌磺钠、氟啶胺、噻菌铜、氟噻唑吡乙酮、磷酸二氢钾、硫磺、氢氧化铜、活化酯或氟唑活化酯中的任意一种或至少两种的组合。
优选地,所述杀虫剂选自噻虫嗪、吡虫啉、噻虫胺、噻虫啉、啶虫脒、烯啶虫胺、呋虫胺、氟啶虫胺腈、多杀菌素、乙基多杀菌素、毒死蜱、丁硫克百威、丙硫克百威、氟虫腈、乙虫腈、高效氯氟氰菊酯、氯菊酯、甲氰菊酯、醚菊酯、溴氰菊酯、氯氰菊酯、氟氯氰菊酯、联苯菊酯、顺式氰戊菊酯、顺式氯氰菊酯、除虫菊素、阿维菌素、甲氨基阿维菌素苯甲酸盐、吡丙醚、苯氧威、吡蚜酮、氟啶虫酰胺、氟虫脲、虱螨脲、双氟虫脲、氟啶脲、除虫脲、氟环脲、氟铃脲、氟酰脲、多氟脲、杀铃脲、环虫酰肼、甲氧虫酰肼、虫酰肼、氯虫酰肼、唑虫酰胺、茚虫威、氰氟虫腙、螺虫乙酯、氯虫苯甲酰胺、氟苯虫酰胺、溴氰虫酰胺、环溴虫酰胺、四氯虫酰胺、tetraniliprole或broflanilide中的任意一种或至少两种的组合。
优选地,所述杀螨剂选自四螨嗪、噻螨酮、乙螨唑、唑螨醚、唑螨酯、嘧螨醚、哒螨灵、吡螨胺、联苯肼酯、克螨特、苯丁锡、丁氟螨酯、腈吡螨酯、双甲脒、灭螨醌、喹螨醚、三唑锡、三环锡、溴螨酯、氟螨嗪、嘧螨酯、磺胺螨酯、螺螨酯或螺甲螨酯中的任意一种或至少两种的组合。
进一步优选地,所述有效成分B选自丙硫菌唑、苯醚甲环唑、氟环唑、戊唑醇、己唑醇、腈菌唑、三唑酮、嘧菌酯、肟菌酯、啶氧菌酯、吡唑醚菌酯、甲霜灵、噻呋酰胺、双炔酰菌胺、啶酰菌胺、氟唑菌酰羟胺、氟吡菌胺、稻瘟酰胺、氟吡菌酰胺、咪鲜胺、霜霉威盐酸盐、多菌灵、甲基硫菌灵、井冈霉素、春雷霉素、烯酰吗啉、氟吗啉、乙嘧酚、福美双、代森锌、代森锰锌、三乙膦酸铝、百菌清、稻瘟灵、咯菌腈、氟啶胺、氟唑活化酯、噻虫嗪、吡虫啉、噻虫胺、多杀菌素、乙基多杀菌素、毒死蜱、氟虫腈、乙虫腈、高效氯氟氰菊酯、醚菊酯、溴氰菊酯、氟氯氰菊酯、阿维菌素、呋虫胺、啶虫脒、甲氨基阿维菌素苯甲酸盐、吡蚜酮、氟啶虫酰胺、氯虫苯甲酰胺或溴氰虫酰胺中的任意一种或至少两种的组合。
进一步优选地,所述有效成分B选自丙硫菌唑、苯醚甲环唑、氟环唑、戊唑醇、己唑醇、腈菌唑、三唑酮、嘧菌酯、肟菌酯、啶氧菌酯、吡唑醚菌酯、噻呋酰胺、啶酰菌胺、稻瘟酰胺、氟吡菌酰胺、咪鲜胺、多菌灵、甲基硫菌灵、井冈霉素、春雷霉素、乙嘧酚、福美双、代森锰锌、百菌清、稻瘟灵、咯菌腈、噻虫嗪、吡虫啉、噻虫胺、呋虫胺、氟虫腈、氯虫苯甲酰胺或溴氰虫酰胺中的任意一种或至少两种的组合。
作为本发明的优选技术方案,所述含有酰胺类化合物的药物组合物为以如下表2中所述酰胺类化合物(有效成分A)和有效成分B为有效成分的药物组合物:
表2
其中酰胺类化合物的编号与如上表1中所列举出的化合物的编号相对应。
优选地,本发明所述有效成分A和有效成分B的重量比是200:1-1:200,例如200:1、180:1、150:1、130:1、100:1、80:1、60:1、40:1、20:1、10:1、1:1、1:10、1:30、1:50、1:80、1:100、1:120、1:140、1:160、1:180或1:200等。
在本发明中,所述含有酰胺类化合物的药物组合物根据其含有的有效成分A和有效成分B的不同,其优选重量配比不同,作为本发明的优选技术方案,当含有酰胺类化合物的药物组合物的有效成分A和有效成分B选择表3中所述成分时,其优选的重量配比以及特别优选的重量配比如表3所示。
表3
另一方面,本发明提供了如上所述的含有酰胺类化合物的药物组合物在农业、林业、园艺上防治植物病害或虫害中的应用。
本发明的含有酰胺类化合物的药物组合物适用于防治危害水稻、果树、蔬菜、其它作物及花卉等的各种农林、园艺病害和虫害。
另一方面,本发明提供了如上所述的含有酰胺类化合物的药物组合物在植物、作物或花卉的种子处理中的应用。
在本发明中,所述植物病害包括真菌、细菌、病毒引起的病害。
优选地,所述真菌病害包括卵菌(Oomycetes)、子囊菌(Ascomycetes)、担子菌(Basidiomycetes)或半知菌(Deuteromycetes)病害。
优选地,所述植物病害包括但不限于:小麦锈病、小麦白粉病、小麦赤霉病、小麦根腐病、小麦纹枯病、小麦全蚀病、小麦颖枯病、黄瓜霜霉病、黄瓜白粉病、黄瓜炭疽病、黄瓜枯萎病、黄瓜灰霉病、葡萄霜霉病、番茄早疫病、番茄晚疫病、水稻纹枯病、水稻稻瘟病、西瓜蔓枯病、花生疮痂病、花生黑斑病、柑橘疮痂病、辣椒根腐病、棉花黄萎病、棉花枯萎病、油菜黑茎病、油菜菌核病、梨黑星病、人参锈腐病、玉米锈病、玉米弯孢病、玉米大斑病、芒果蒂腐病、苹果轮纹病、苹果腐菌烂病、香蕉叶斑病、大豆锈病或马铃薯晚疫病。
优选地,所述植物病害包括小麦锈病、小麦白粉病、小麦赤霉病、小麦纹枯病、水稻纹枯病、黄瓜白粉病、香蕉叶斑病或大豆锈病。
本发明组合物应用范围广泛,所应用的植物主要包括以下几类:蔬菜类,黄瓜、丝瓜、西瓜、甜瓜、南瓜、吊瓜、菠菜、芹菜、甘蓝、白菜、葫芦、辣椒、茄子、番茄、葱、姜、蒜、韭菜、草莓、莴笋、菜豆、豇豆、蚕豆、萝卜、胡萝卜、马铃薯、山药;禾谷类,小麦、大麦、水稻、玉米、高粱、甘薯;果树类,苹果、梨、香蕉、柑橘、葡萄、荔枝、芒果;花卉类,牡丹、月季、火鹤;油料作物,花生、大豆、油菜、向日葵、芝麻;糖料作物,甜菜、甘蔗;其他作物,如烟草和茶,以上列举植物对农药组合物使用范围无限制作用。
另一方面,本发明提供一种药物制剂,所述药物制剂包括如上所述的含有酰胺类化合物的药物组合物和农药学上可接受的载体。
优选地,所述农药制剂中,含有酰胺类化合物的药物组合物的重量百分比为1-99%,例如1%、3%、5%、8%、10%、15%、18%、20%、25%、30%、35%、40%、45%、50%、55%、60%、65%、70%、75%、80%、85%、90%、95%或99%。
优选地,所述农药学上可接受的载体包括表面活性剂。
在本发明中,所述表面活性剂为离子型表面活性剂或非离子型表面活性剂。
所述表面活性剂包括分散剂、润湿剂、乳化剂、防冻剂、增稠剂、消泡剂、防腐剂、稳定剂、染色剂、填料和溶剂。乳化剂可以为十二烷基苯磺酸盐、烷基萘磺酸盐、烷基磺酸盐、烷基酚聚氧乙烯醚、苄基酚聚氧乙烯、苯乙基酚聚氧乙烯醚、脂肪胺聚氧乙烯醚等。分散剂包括木质素磺酸盐、烷基酚聚氧乙烯醚、萘磺酸甲醛缩合物钠盐、脂肪胺聚氧乙烯醚、脂肪酸聚氧乙烯酯、甘油脂肪酸酯聚氧乙烯醚、聚羧酸盐、甲醛缩合物、烷基苯磺酸钙盐、烷基酚聚氧乙烯醚等。润湿剂选自十二烷基硫酸钠、烷基萘磺酸盐、拉开粉BX、聚氧乙烯醚、EO/PO嵌段聚醚、脂肪醇聚氧乙烯醚、脂肪醇聚氧乙烯醚硫酸盐、烷基磷酸钠、烷基萘磺酸盐、烷基酚聚氧乙烯基硫酸钠。乳化剂选自十二烷基苯磺酸盐、烷基萘磺酸盐、烷基磺酸盐、烷基酚聚氧乙烯醚、苄基酚聚氧乙烯、苯乙基酚聚氧乙烯醚、脂肪胺聚氧乙烯醚。防冻剂选自乙二醇、丙二醇和丙三醇。增稠剂选自黄原胶、羟甲基纤维素、羟乙基纤维素、羟丙基淀粉、甲基纤维素、淀粉磷酸酯钠、硅酸镁铝和聚乙烯醇。消泡剂选自硅油、硅酮类化合物、磷酸三丁酯、C10~20饱和脂肪酸类化合物和聚醚类消泡剂。防腐剂选自甲醛、水杨酸苯酯、对羟基苯甲酸丁酯和山梨酸钾,所述稳定剂选自亚磷酸三苯酯、环氧氯苯烷、环氧大豆油和硅酸镁铝,所述染色剂选自偶氮颜料、氧化钛和氧化铁。
优选地,所述农药学上可接受的载体包括固体载体和/或液体载体。
优选地,所述固体载体包括天然的或合成的粘土和硅酸盐,例如天然硅石和硅藻土;硅酸镁例如滑石;硅酸铝镁例如高岭石、高岭土、蒙脱土和云母;白碳黑、碳酸钙、轻质碳酸钙;硫酸钙;石灰石;硫酸钠;胺盐如硫酸铵、六甲撑二胺。液体载体包括水和有机溶剂,当用水做溶剂或稀释剂时,有机溶剂也能用做辅助剂或防冻添加剂。合适的有机溶剂包括芳烃例如三甲苯、苯、二甲苯、甲苯等;氯代烃,例如氯代苯、氯乙烯、三氯甲烷、二氯甲烷等;脂肪烃,例如石油馏分、环己烷、轻质矿物油;醇类,例如异丙醇、丁醇、乙二醇、丙三醇和环己醇等;以及它们的醚和酯;还有酮类,例如丙酮、环己酮以及二甲基甲酰胺和N-甲基-吡咯烷酮。
在杀菌剂组合物的配制过程中可以将活性组分与液体载体和/或固体载体混合,同时加入表面活性剂(如乳化剂、分散剂、稳定剂、湿润剂等),还可以加入其它助剂(如粘合剂、消泡剂、防冻剂、氧化剂等)。
优选地,所述药物制剂的剂型为溶液剂、悬浮剂、乳油剂、粉剂、乳剂、颗粒剂或种衣剂。
另一方面,本发明提供一种防治植物病害的方法,所述方法为:向需要控制的植物病害或其生长的介质上施用有效剂量的如上所述的含有酰胺类化合物的药物组合物。
优选地,所述有效剂量为每公顷10-1000g,例如10g、20g、50g、80g、100g、120g、150g、180g、200g、250g、300g、350g、400g、450g、500g、600g、700g、800g、900g或1000g,优选每公顷20-500g。
本发明的组合物可以制剂的形式施用在病害或其生长介质上。通式化合物I作为活性组分溶解或分散于载体中或配制成制剂以便作为杀菌剂使用时更易于分散。例如:这些化学制剂可被配制成可溶液剂(SL)、可溶粉剂(SP)、可溶粒剂(SG)、乳油(EC)、可湿性粉剂(WP)、水乳剂(EW)、悬浮剂(SC)、可分散油悬浮剂(OD)、水分散粒剂(WG)、微囊悬浮剂(CS)、颗粒剂(GR)、微乳剂(ME)、悬浮乳剂(SE)、微囊悬浮-悬浮剂(ZC)、悬浮种衣剂(FSC)、种子处理干粉剂(DS)、种子处理悬浮剂(FS)、种子处理可溶粉剂(SS)、种子处理可分散粉剂(WS)、种子处理乳剂(ES)、种子处理液剂(LS)等。
相对于现有技术,本发明具有以下有益效果:
本发明的含有酰胺类化合物的药物组合物与传统杀菌剂相比使用中具有以下优点:
(1)本发明中有效成分A和有效成分B具有协同增效作用,药剂使用量较单一活性成分杀菌剂大大降低,防治效果显著提高;
(2)扩大了防治谱,可应用于蔬菜、果树、花卉、禾谷、油料、糖料等作物及园艺、林业上的多种病虫害;
(3)延缓药剂抗药性产生,选取两种或多种作用机理的化合物组合使用,可以有效防止或减缓病原菌对一类作用机理的化合物产生抗药性。
具体实施方式
下面通过具体实施方式来进一步说明本发明的技术方案。本领域技术人员应该明了,所述实施例仅仅是帮助理解本发明,不应视为对本发明的具体限制。
合成实施例
合成实施例1
N-(2-(2-异丙基-5-甲基苯氧基)苯基)-2-甲基-4-(三氟甲基)噻唑-5-甲酰胺(化合物2)的制备:
步骤1:1-异丙基-4-甲基-2-(2-硝基苯氧基)苯的合成:
取一反应瓶,将邻氟硝基苯(购买自上海泰坦科技股份有限公司,70.87mmol,1.0eq)、碳酸钾(70.87mmol,1.0eq)加入到60mL DMF中,回流条件下加入2-异丙基-5-甲基苯酚(购买自上海泰坦科技股份有限公司,77.96mmol,1.1eq),保持温度反应2-3h,待反应完毕后,加水200mL,乙酸乙酯萃取,有机层经饱和食盐水洗涤、无水硫酸钠干燥后,减压下浓缩,得到淡黄色油状粗产物1-异丙基-4-甲基-2-(2-硝基苯氧基)苯(11.9g,收率62%),未经分离,直接进行下一步反应。
步骤2:2-(2-异丙基-5-甲基苯氧基)苯胺的合成:
向反应瓶中依次加入1-异丙基-4-甲基-2-(2-硝基苯氧基)苯(43.86mmol,1.0eq)、乙醇(60mL)、5%钯碳(1.19g),将水合肼(175.44mmol,4eq)缓慢滴加到上述体系中,室温反应4h,待反应完毕后,过滤除去钯碳,滤液中加入水,乙酸乙酯萃取,有机层经饱和食盐水洗涤、无水硫酸钠干燥后,减压下浓缩,残余物经柱色谱提纯(淋洗液为石油醚:乙酸乙酯=25:1),得淡黄色油状产物2-(2-异丙基-5-甲基苯氧基)苯胺(6.03g,收率57%)。
步骤3:N-(2-(2-异丙基-5-甲基苯氧基)苯基)-2-甲基-4-(三氟甲基)噻唑-5-甲酰胺的合成:
向反应瓶中依次加入2-(2-异丙基-5-甲基苯氧基)苯胺(2.07mmol,1.0eq)、二氯甲烷(20mL)和三乙胺(2.20mmol,1.06eq),缓慢滴加2-甲基-4-(三氟甲基)噻唑-5-碳酰氯(2.18mmol,1.05eq)。室温下反应2h,向反应液中加水淬灭反应,用二氯甲烷萃取,有机层经饱和食盐水洗涤、无水硫酸钠干燥后,减压下浓缩,残余物经柱色谱提纯(淋洗液为石油醚:乙酸乙酯=20:1),得黄色油状产物N-(2-(2-异丙基-5-甲基苯氧基)苯基)-2-甲基-4-(三氟甲基)噻唑-5-甲酰胺(化合物2,333.1mg,收率37%)。
化合物2的1H NMR(500MHz,CDCl3)核磁数据如下(δ[ppm]):8.68(s,1H),8.51(d,J=7.9Hz,1H),7.29(s,1H),7.11(td,J=7.9,1.3Hz,1H),7.06(dd,J=8.0,1.6Hz,1H),7.03(d,J=7.7Hz,1H),6.72(s,1H),6.67(dd,J=8.1,1.4Hz,1H),3.24-3.12(m,1H),2.78(s,3H),2.30(s,3H),1.22(s,3H),1.21(s,3H)。
合成实施列2
N-(2-(2-叔丁基-5-甲基苯氧基)苯基)-2-甲基-4-(三氟甲基)噻唑-5-甲酰胺(化合物3)的制备:
步骤1:1-叔丁基-4-甲基-2-(2-硝基苯氧基)苯的合成:
取一反应瓶,将邻氟硝基苯(70.87mmol,1.0eq)、碳酸钾(70.87mmol,1.0eq)溶于60mL DMF,回流条件下加入2-(叔丁基)-5-甲基苯酚(购买自上海泰坦科技股份有限公司,77.96mmol,1.1eq),保持温度反应2-3h,待反应完毕后,加入200mL水,乙酸乙酯萃取,有机层经饱和食盐水洗涤、无水硫酸钠干燥后,减压下浓缩,得到褐色油状粗产物1-叔丁基-4-甲基-2-(2-硝基苯氧基)苯(18.2g,收率90%),未经分离,直接进行下一步反应。
步骤2:2-(2-叔丁基-5-甲基苯氧基)苯胺的合成:
向反应瓶中依次加入1-叔丁基-4-甲基-2-(2-硝基苯氧基)苯(63.78mmol,1.0eq)、乙醇(60mL)、5%钯碳(1.82g),将水合肼(255.14mmol,4eq)缓慢滴加到上述体系中,室温反应4h,待反应完毕后,过滤除去钯碳,用水淬灭反应,乙酸乙酯萃取,有机层经饱和食盐水洗涤、无水硫酸钠干燥后,减压下浓缩,残余物经柱色谱提纯(淋洗液为石油醚:乙酸乙酯=10:1),得浅褐色油状产物2-(2-叔丁基-5-甲基苯氧基)苯胺(13.03g,收率80%)。
步骤3:N-(2-(2-叔丁基-5-甲基苯氧基)苯基)-2-甲基-4-(三氟甲基)噻唑-5-甲酰胺的合成:
向反应瓶中依次加入2-(2-叔丁基-5-甲基苯氧基)苯胺(1.96mmol,1.0eq)、二氯甲烷(20mL)、三乙胺(2.08mmol,1.06eq),缓慢滴加2-甲基-4-(三氟甲基)噻唑-5-碳酰氯(2.06mmol,1.05eq)。室温下反应2h,向反应液中加水淬灭反应,用二氯甲烷萃取,有机层经饱和食盐水洗涤、无水硫酸钠干燥后,减压下浓缩,残余物经柱色谱提纯(淋洗液为石油醚:乙酸乙酯=10:1),得褐色油状产物N-(2-(2-叔丁基-5-甲基苯氧基)苯基)-2-甲基-4-(三氟甲基)噻唑-5-甲酰胺(化合物3,509.4mg,收率58%)。
化合物3的1H NMR(400MHz,DMSO)核磁数据如下(δ[ppm]):10.54(s,1H),7.71(d,J=7.1Hz,1H),7.26(d,J=8.0Hz,1H),7.23-7.17(m,1H),7.12(t,J=7.6Hz,1H),6.90(d,J=8.0Hz,1H),6.73(d,J=8.1Hz,1H),6.57(s,1H),2.73(s,3H),2.18(s,3H),1.33(s,9H)。
合成实施例3
N-(2-(5-甲基-2-(叔戊基)苯氧基)苯基)-1-甲基-3-三氟甲基-1H-吡唑-4-甲酰胺(化合物64)的制备:
步骤1:5-甲基-2-叔戊基苯酚的合成:
取一反应瓶,将间甲基苯酚(92.47mmol,1.0eq)用二氯甲烷溶解,冰浴条件下依次滴入2-甲基-2-丁醇(90.47mmol,1.0eq)和浓硫酸(90.47mmol,1.0eq),室温搅拌5-6h,待反应完毕后,用饱和碳酸氢钠水溶液淬灭反应,二氯甲烷萃取,有机层经饱和食盐水洗涤、无水硫酸钠干燥后,减压下浓缩,残余物经柱色谱提纯(淋洗液为石油醚:乙酸乙酯=50:1),得到无色油状产物5-甲基-2-叔戊基苯酚(14.84g,收率90%)。
步骤2:4-甲基-2-(2-硝基苯氧基)-1-叔戊基苯的合成:
取一反应瓶,将邻氟硝基苯(63.78mmol,1.0eq)、碳酸钾(63.78mmol,1.0eq)溶于60mL DMF,回流条件下加入5-甲基-2-叔戊基苯酚(70.16mmol,1.1eq),保持温度反应2-3h,待反应完毕后,用水淬灭反应,乙酸乙酯萃取,有机层经饱和食盐水洗涤、无水硫酸钠干燥后,减压下浓缩,得到浅褐色油状粗产物4-甲基-2-(2-硝基苯氧基)-1-叔戊基苯(17.18g,收率90%),未经分离,直接进行下一步反应。
步骤3:2-(2-叔戊基-5-甲基苯氧基)苯胺的合成:
向反应瓶中依次加入4-甲基-2-(2-硝基苯氧基)-1-叔戊基苯(57.39mmol,1.0eq)、乙醇(60mL)、5%钯碳(1.72g),将水合肼(229.55mmol,4eq)缓慢滴加到上述体系中,室温反应4h,待反应完毕后,过滤除去钯碳,用水淬灭反应,乙酸乙酯萃取,有机层经饱和食盐水洗涤、无水硫酸钠干燥后,减压下浓缩,残余物经柱色谱提纯(淋洗液为石油醚:乙酸乙酯=50:1),得到淡黄色油状产物2-(2-叔戊基-5-甲基苯氧基)苯胺(12.68g,收率82%)。
步骤4:N-(2-(5-甲基-2-(叔戊基)苯氧基)苯基)-1-甲基-3-三氟甲基-1H-吡唑-4-甲酰胺的合成:
向反应瓶中依次加入2-(2-叔戊基-5-甲基苯氧基)苯胺(1.48mmol,1.0eq)、二氯甲烷(20mL)、三乙胺(1.57mmol,1.06eq),缓慢滴加1-甲基-3-三氟甲基-1H-吡唑-4-碳酰氯(1.56mmol,1.05eq)。室温下反应2h,向反应液中加水淬灭反应,用二氯甲烷萃取,有机层经饱和食盐水洗涤、无水硫酸钠干燥后,减压下浓缩,残余物经柱色谱提纯(淋洗液为石油醚:乙酸乙酯=10:1),得白色固体产物N-(2-(5-甲基-2-(叔戊基)苯氧基)苯基)-1-甲基-3-三氟甲基-1H-吡唑-4-甲酰胺(化合物64,601.9mg,收率91%)。
化合物64的1H NMR(400MHz,DMSO)数据如下(δ[ppm]):9.58(s,1H),8.42(s,1H),7.66(dd,J=7.8,1.5Hz,1H),7.21-7.14(m,2H),7.10(td,J=7.7,1.3Hz,1H),6.89(dd,J=8.0,1.0Hz,1H),6.75(dd,J=8.1,1.2Hz,1H),6.59(s,1H),3.95(s,3H),2.19(s,3H),1.71(q,J=7.4Hz,2H),1.26(s,6H),0.56(t,J=7.4Hz,3H)。
合成实施列4
N-(2-(2-叔丁基-5-异丙基苯氧基)苯基)-1-甲基-3-三氟甲基-1H-吡唑-4-甲酰胺(化合物68)的制备:
步骤1:2-叔丁基-5-异丙基苯酚的合成:
取一反应瓶,将间异丙基苯酚(购买自上海泰坦科技股份有限公司,73.43mmol,1.0eq)用二氯甲烷溶解,冰浴条件下依次滴入叔丁醇(73.43mmol,1.0eq)和浓硫酸(73.43mmol,1.0eq),室温搅拌5-6h,待反应完毕后,用饱和碳酸氢钠水溶液淬灭反应,二氯甲烷萃取,有机层经饱和食盐水洗涤、无水硫酸钠干燥后,减压下浓缩,残余物经柱色谱提纯(淋洗液为石油醚:乙酸乙酯=25:1),得到淡黄色油状产物2-叔丁基-5-异丙基苯酚(12.14g,收率86%)。
步骤2:1-叔丁基-4-异丙基-2-(2-硝基苯氧基)苯的合成:
取一反应瓶,将邻氟硝基苯(29.77mmol,1.0eq)、碳酸钾(29.77mmol,1.0eq)溶于60mL DMF,回流条件下加入2-叔丁基-5-异丙基苯酚(32.74mmol,1.1eq),保持温度反应6-7h,待反应完毕后,用水淬灭反应,乙酸乙酯萃取,有机层经饱和食盐水洗涤、无水硫酸钠干燥后,减压下浓缩,得到淡黄色油状粗产物1-叔丁基-4-异丙基-2-(2-硝基苯氧基)苯(8.68g,收率93%),未经分离,直接进行下一步反应。
步骤3:2-(2-叔丁基-5-异丙基苯氧基)苯胺的合成:
向反应瓶中依次加入1-叔丁基-4-异丙基-2-(2-硝基苯氧基)苯(27.70mmol,1.0eq)、乙醇(60mL)、5%钯碳(868mg),将水合肼(110.79mmol,4eq)缓慢滴加到上述体系中,室温反应4h,待反应完毕后,过滤除去钯碳,用水淬灭反应,乙酸乙酯萃取,有机层经饱和食盐水洗涤、无水硫酸钠干燥后,减压下浓缩,残余物经柱色谱提纯(淋洗液为石油醚:乙酸乙酯=25:1),得到褐色油状产物2-(2-叔丁基-5-异丙基苯氧基)苯胺(6.28g,收率80%)。
步骤4:N-(2-(2-叔丁基-5-异丙基苯氧基)苯基)-1-甲基-3-三氟甲基-1H-吡唑-4-甲酰胺的合成:
向反应瓶中依次加入2-(2-叔丁基-5-异丙基苯氧基)苯胺(1.41mmol,1.0eq)、二氯甲烷(20mL)、三乙胺(1.50mmol,1.06eq),缓慢滴加1-甲基-3-三氟甲基-1H-吡唑-4-碳酰氯(1.48mmol,1.05eq)。室温下反应2h,向反应液中加水淬灭反应,用二氯甲烷萃取,有机层经饱和食盐水洗涤、无水硫酸钠干燥后,减压下浓缩,残余物经柱色谱提纯(淋洗液为石油醚:乙酸乙酯=4:1),得淡黄色固体产物N-(2-(2-叔丁基-5-异丙基苯氧基)苯基)-1-甲基-3-三氟甲基-1H-吡唑-4-甲酰胺(化合物68,447.5mg,收率69%)。
化合物68的1H NMR(400MHz,DMSO)数据如下(δ[ppm]):9.64(s,1H),8.44(s,1H),7.93-7.56(m,1H),7.29(d,J=8.1Hz,1H),7.16(t,J=7.7Hz,1H),7.09(t,J=7.5Hz,1H),6.97(d,J=8.1Hz,1H),6.72(d,J=8.1Hz,1H),6.67(s,1H),3.95(s,3H),2.83-2.70(m,1H),1.31(s,9H),1.11(s,3H),1.10(s,3H).
参照合成实施例1-4的方法,合成了表4中的化合物。
表3
其他化合物可以通过选择不同的原料,用类似方法制备。
制剂实施例
制剂实施例1、 20%化合物101·井冈霉素可溶液剂
表5
制备方法:在250ml三口烧瓶里面,加入59.9份去离子水,将12份异丙醇、8份烷基糖苷加入,混匀,然后加入10份化合物(101)、8份井冈霉素,加热到40~50度搅拌1.5小时,最后加入0.1份消泡剂1522,即得到20%井冈霉素和化合物(101)组合的可溶液剂。
制剂实施例2、 16%化合物2·氟唑活化酯乳油
表6
名称 | 折百(W/W,%) | 备注 |
化合物2 | 15 | 活性成分 |
氟唑活化酯 | 1 | 活性成分 |
十二烷基苯磺酸钙 | 5 | 乳化剂 |
蓖麻油聚氧乙烯醚 | 4 | 乳化剂 |
三甲苯 | 75 | 溶剂 |
制备方法:在250ml三口烧瓶里面,加入75份三甲苯,将15份化合物2,1份氟唑活化酯、5份十二烷基苯磺酸钙、4份蓖麻油聚氧乙烯醚加入,度搅拌1小时,即得到16%化合物2·氟唑活化酯乳油。
制剂实施例3、 50%化合物59·百菌清可湿性粉剂
表7
名称 | 折百(W/W,%) | 备注 |
化合物59 | 5 | 活性成分A |
百菌清 | 45 | 活性成分B |
十二烷基硫酸钠 | 2 | 润湿剂 |
木质素磺酸钠 | 8 | 分散剂 |
高岭土 | 40 | 载体 |
制备方法:称取5份化合物59、45份百菌清、2份十二烷基硫酸钠、8份木质素磺酸钠、40高岭土,混合均匀后,用气流粉碎机粉碎至平均粒剂10微米,即得到50%化合物59·百菌清可湿性粉剂。
制剂实施例4、 30%化合物3·肟菌酯水乳剂
表8
名称 | 折百(W/W,%) | 备注 |
化合物3 | 10 | 活性成分A |
肟菌酯 | 20 | 活性成分B |
三苯乙烯基苯酚聚氧乙烯醚磷酸酯 | 2 | 分散剂 |
蓖麻油聚氧乙烯醚 | 4 | 乳化剂 |
丙二醇 | 4 | 防冻剂 |
三甲苯 | 20 | 溶剂 |
1%黄原胶溶液 | 10 | 增稠剂 |
卡松 | 0.1 | 防腐剂 |
去离子水 | 29.9 | 载体 |
制备方法:称取10份化合物3、20份肟菌酯、4份蓖麻油聚氧乙烯醚、20份三甲苯,于40~50℃溶解均匀,作为a相;另取29.9份去离子水、4份丙二醇、2份三苯乙烯基苯酚聚氧乙烯醚磷酸酯搅拌溶解均匀,作为b相;在高剪切下,将a相缓慢加入b相,剪切至平均粒径1.5微米,加入0.1份卡松,10份1%黄原胶溶液搅拌30分钟,即得到30%化合物3·肟菌酯水乳剂。
制剂实施例5、 40%化合物60·嘧菌酯悬浮剂
表9
名称 | 折百(W/W,%) | 备注 |
化合物60 | 20 | 活性成分A |
嘧菌酯 | 20 | 活性成分B |
脂肪醇聚氧乙烯醚 | 1 | 润湿剂 |
三苯乙烯基苯酚聚氧乙烯醚磷酸酯 | 2 | 分散剂 |
聚丙烯酸酯 | 4 | 分散剂 |
丙二醇 | 4 | 防冻剂 |
1%黄原胶溶液液 | 10 | 增稠剂 |
卡松 | 0.1 | 防腐剂 |
1522 | 0.2 | 有机硅消泡剂 |
去离子水 | 38.7 | 载体 |
制备方法:称取38.7份去离子水、4份丙二醇、2份三苯乙烯基苯酚聚氧乙烯醚磷酸酯、1份脂肪醇聚氧乙烯醚、4份聚丙烯酸酯、0.1份卡松、0.2份消泡剂1522搅拌溶解均匀,加入20份嘧菌酯和20份化合物60剪切均匀,然后通过砂磨机研磨至平均粒径2微米,加入10份1%黄原胶溶液搅拌30分钟,即得到40%化合物3·嘧菌酯悬浮剂。
制剂实施例6、 60%化合物72·丙硫菌唑水分散粒剂
表10
名称 | 折百(W/W,%) | 备注 |
化合物72 | 20 | 活性成分A |
丙硫菌唑 | 40 | 活性成分B |
十二烷基硫酸钠 | 1 | 润湿剂 |
木质素磺酸钠 | 4 | 分散剂 |
萘甲醛聚合物磺酸钠 | 4 | 分散剂 |
硫酸铵 | 3 | 崩解剂 |
玉米淀粉 | 10 | 填料 |
高岭土 | 18 | 填料 |
制备方法:称取20份化合物72、40份丙硫菌唑、1份十二烷基硫酸钠、4份木质素磺酸钠、4份萘甲醛聚合物磺酸钠、3份硫酸铵、10份玉米淀粉、18份高岭土混合均匀,通过气流粉碎机粉碎至平均粒径10~15微米,加入粉体量的15%的水捏合,然后通过旋转挤压造粒,50℃烘干3小时,筛分,即得60%化合物72·丙硫菌唑水分散粒剂。
制剂实施例7、 20%化合物64·甲基硫菌灵可分散油悬浮剂
表11
名称 | 折百(W/W,%) | 备注 |
化合物64 | 5 | 活性成分A |
甲基硫菌灵 | 15 | 活性成分B |
脂肪酸聚氧乙烯醚 | 12 | 乳化剂 |
苯乙烯基苯酚聚氧乙烯醚 | 4 | 乳化剂 |
有机膨润土 | 1 | 增稠剂 |
气相白炭黑 | 1 | 稳定剂 |
油酸甲酯 | 62 | 载体 |
制备方法:称取62份油酸甲酯、12份脂肪酸聚氧乙烯醚、4苯乙烯基苯酚聚氧乙烯醚搅拌溶解均匀,加入5份化合物64、15份甲基硫菌灵、1份有机膨润土、1份气相白炭黑剪切均匀,然后通过砂磨机研磨至平均粒径4微米,即得到20%化合物64·甲基硫菌灵可分散油悬浮剂。
制剂实施例8、 30%化合物106·咯菌清·噻虫嗪悬浮种衣剂
表12
名称 | 折百(W/W,%) | 备注 |
化合物106 | 10 | 活性成分A |
咯菌清 | 15 | 活性成分B |
噻虫嗪 | 5 | 活性成分B |
脂肪醇聚氧乙烯醚 | 1 | 润湿剂 |
三苯乙烯基苯酚聚氧乙烯醚磷酸酯 | 4 | 分散剂 |
10%黄原胶溶液 | 10 | 增稠剂 |
聚乙烯醇1799 | 1 | 成膜剂剂 |
染料 | 1 | 着色剂 |
1522 | 0.2 | 消泡剂 |
卡松 | 0.1 | 防腐剂 |
尿素 | 3 | 防冻剂 |
去离子水 | 49.7 | 载体 |
制备方法:称取49.7份去离子水、3份尿素、0.2份1522、1份染料、1份聚乙烯醇1799、4份三苯乙烯基苯酚聚氧乙烯醚磷酸酯、1份脂肪醇聚氧乙烯醚、0.1份卡松搅拌溶解均匀,加入10份化合物106、15份咯菌清、5份噻虫嗪剪切均匀,然后通过砂磨机研磨至平均粒径2微米,加入10份1%黄原胶溶液搅拌30分钟,即得到30%化合物106·咯菌清·噻虫嗪悬浮种衣剂。
制剂实施例9 25%化合物110·吡唑醚菌酯微囊悬浮剂
表13
名称 | 折百(W/W,%) | 备注 |
化合物110 | 15 | 活性成分A |
吡唑醚菌酯 | 10 | 活性成分B |
多芳基多亚甲基多异氰酸酯 | 3 | 囊材 |
三苯乙烯基苯酚聚氧乙烯醚磷酸酯 | 2 | 分散剂 |
蓖麻油聚氧乙烯醚 | 4 | 乳化剂 |
丙二醇 | 4 | 防冻剂 |
三甲苯 | 20 | 溶剂 |
己二胺 | 0.5 | 囊材 |
1%黄原胶溶液 | 10 | 增稠剂 |
卡松 | 0.1 | 防腐剂 |
1522 | 0.2 | 消泡剂 |
去离子水 | 31.2 | 载体 |
制备方法:称取15份化合物110、10份吡唑醚菌酯、3份多芳基多亚甲基多异氰酸酯、4份蓖麻油聚氧乙烯醚、20份三甲苯,于40~50度溶解均匀,作为A相;另取31.2份去离子水、4份丙二醇、2份三苯乙烯基苯酚聚氧乙烯醚磷酸酯搅拌溶解均匀,作为B相;在高剪切下,将A相缓慢加入B相,剪切至平均粒径2~3微米,然后将物料加入到三口烧瓶里,加入0.5份己二胺,于50~60度搅拌反应10小时,加入0.1份卡松,0.2份1522,10份1%黄原胶溶液搅拌30分钟,即得到25%化合物110·吡唑醚菌酯微囊悬浮剂。
生测实施例
生测实施例1
在本实施例中,对制备得到的酰胺类化合物对防治黄瓜白粉病(Erysiphecichoracearum)的效果进行测定,方法如下:
筛选采用活体盆栽测定方法,即将待测化合物样品用少量溶剂(溶剂的种类如丙酮、甲醇、DMF等,依据其对样品的溶解能力而选择,溶剂量与喷液量的体积比等于或小于0.05)溶解,用含有0.1%吐温80的水稀释,配制成所需浓度待测液。温室培养的两叶期黄瓜苗作为黄瓜白粉病(Erysiphe cichoracearum)的试验寄主植物。用本发明化合物按照设计浓度进行叶面喷雾处理。另设喷清水的空白对照,3次重复,处理后24h后进行病菌接种。接种后,将植物放在人工气候室中保湿培养(温度:昼25℃、夜20℃,相对湿度:95-99%)。试验材料培养24h后,移置温室培养。待对照充分发病后(通常为一周时间)进行化合物防病效果评估。结果调查参照美国植病学会编写的《A Manual of Assessment Keys for PlantDiseases》,用100~0来表示,以“100”级代表无病和“0”级代表最严重的发病程度。
化合物59、60、68、104在浓度为400ppm时对黄瓜白粉病的防治效果≥90%。
生测实施例2
在本实施例中,对制备得到的酰胺类化合物对防治黄瓜霜霉病(Pseudoperonospora cubensis)的效果进行测定,方法如下:
筛选采用活体盆栽测定方法,即将待测化合物样品用少量溶剂(溶剂的种类如丙酮、甲醇、DMF等,依据其对样品的溶解能力而选择,溶剂量与喷液量的体积比等于或小于0.05)溶解,用含有0.1%吐温80的水稀释,配制成所需浓度待测液。温室培养的两叶期黄瓜苗作为黄瓜霜霉病(Pseudoperonospora cubensis)的试验寄主植物。用本发明化合物按照设计浓度进行叶面喷雾处理。另设喷清水的空白对照,3次重复,处理后24h后进行病菌接种。接种后,将植物放在人工气候室中保湿培养(温度:昼25℃、夜20℃,相对湿度:95-99%)。试验材料培养24h后,移置温室培养。待对照充分发病后(通常为一周时间)进行化合物防病效果评估。结果调查参照美国植病学会编写的《A Manual of Assessment Keys forPlant Diseases》,用100~0来表示,以“100”级代表无病和“0”级代表最严重的发病程度。
化合物59、60在浓度为400ppm时对黄瓜霜霉病的防治效果≥90%。
生测实施例3
在本实施例中,对制备得到的酰胺类化合物对防治大豆锈病(Phakopsorapachyrhizi)的效果进行测定,方法如下:
筛选采用活体盆栽测定方法,即将待测化合物样品用少量溶剂(溶剂的种类如丙酮、甲醇、DMF等,依据其对样品的溶解能力而选择,溶剂量与喷液量的体积比等于或小于0.05)溶解,用含有0.1%吐温80的水稀释,配制成所需浓度待测液。温室培养两叶期大豆作为大豆锈病(Phakopsora pachyrhizi)的试验寄主植物。用本发明化合物按照设计浓度进行叶面喷雾处理。另设喷清水的空白对照,3次重复,处理后24h后进行病菌接种。接种后,将植物放在人工气候室中保湿培养(温度:昼25℃、夜20℃,相对湿度:95-99%)。试验材料培养24h后,移置温室培养。待对照充分发病后(通常为一周时间)进行化合物防病效果评估。结果调查参照美国植病学会编写的《A Manual of Assessment Keys for PlantDiseases》,用100~0来表示,以“100”级代表无病和“0”级代表最严重的发病程度。
化合物2、38、59、60、95、96、133在浓度为100ppm时对大豆锈病的防治效果≥90%。
照以上方法,选取部分本发明化合物与现有化合物KC1、KC2和KC3进行了防治大豆锈病活性的平行测定。试验结果见表14。
表14:部分本发明化合物与对照化合物对大豆锈病防效的比较
生测实施例4
在本实施例中,对制备得到的酰胺类化合物对防治水稻纹枯病(Rhizoctoniasolani)的效果进行测定,方法如下:
采用菌丝生长速率法进行测试,在无菌操作条件下,取配制好的所需浓度待测液,与冷却至70℃左右的无菌培养基混合摇匀(溶解好的培养基置于70℃电热恒温鼓风干燥箱中保温),将含药培养基等量倒入3个直径为9cm的培养皿中,制成相应系列浓度的含药平板。用无菌专用打孔器制作水稻纹枯病病原菌菌饼(直径5mm),自菌落边缘切取菌饼,用接种器将菌饼接种于各含药平板中央,菌丝面朝下,盖上皿盖,置于25℃培养箱中黑暗培养。培养时间为2~3d。待清水对照菌丝直径大于6cm(菌丝直径最大不超过8.5cm)时进行调查。用卡尺测量菌落直径,每个抑菌圈用十字交叉法垂直测量直径各一次。
根据调查结果,按以下两个公式计算各处理浓度对病菌的菌丝生长抑制率,单位为百分率(%),计算结果保留小数点后两位。
菌落增长直径(cm)=菌落直径–菌饼直径(0.5)
菌丝生长抑制率(%)=(空白对照菌落增长直径–药剂处理菌落增长直径)/空白对照菌落增长直径×100%
化合物2、59、60、96在浓度为10ppm时对水稻纹枯病的抑制率≥90%。
照以上方法,选取部分本发明化合物与现有化合物KC1、KC2和KC3进行了抑制水稻纹枯病菌活性的平行测定。试验结果见表15。
表15:部分本发明化合物与现有化合物抑制水稻纹枯病菌活性的比较
供试药剂 | 抑制率(%,0.1ppm) |
化合物2 | 65 |
化合物59 | 64 |
化合物60 | 56 |
化合物96 | 75 |
KC1 | 6 |
KC2 | 10 |
KC3 | 8 |
生测实施例5
在本实施例中,对制备得到的酰胺类化合物对防治马铃薯晚疫病菌(Phytophthora infestans)的效果进行测定,方法如下:
采用菌丝生长速率法进行测试,在无菌操作条件下,取配制好的所需浓度待测液,与冷却至70℃左右的无菌培养基混合摇匀(溶解好的培养基置于70℃电热恒温鼓风干燥箱中保温),将含药培养基等量倒入3个直径为9cm的培养皿中,制成相应系列浓度的含药平板。用无菌专用打孔器制作马铃薯晚疫病病原菌菌饼(直径5mm),自菌落边缘切取菌饼,用接种器将菌饼接种于各含药平板中央,菌丝面朝下,盖上皿盖,置于25℃培养箱中黑暗培养,培养时间为,6~7d。待清水对照菌丝直径大于6cm(菌丝直径最大不超过8.5cm)时进行调查。用卡尺测量菌落直径,每个抑菌圈用十字交叉法垂直测量直径各一次。
根据调查结果,按以下两个公式计算各处理浓度对病菌的菌丝生长抑制率,单位为百分率(%),计算结果保留小数点后两位。
菌落增长直径(cm)=菌落直径–菌饼直径(0.5)
菌丝生长抑制率(%)=(空白对照菌落增长直径–药剂处理菌落增长直径)/空白对照菌落增长直径×100%
化合物2、59、60、68、96、104在浓度为10ppm时对马铃薯晚疫病菌抑制率≥90%。
照以上方法,选取部分本发明化合物与现有化合物KC1、KC2和KC3进行了抑制马铃薯晚疫病菌活性的平行测定。试验结果见表16。
表16:部分本发明化合物与现有化合物抑制马铃薯晚疫病菌活性的比较
供试药剂 | 抑制率(%,0.1ppm) |
化合物2 | 61 |
化合物60 | 76 |
化合物96 | 82 |
化合物104 | 73 |
KC1 | 6 |
KC2 | 1 |
KC3 | 5 |
经过如上生测试实施例1-5对于化合物对病害抑制效果的测定可以看出,本发明式I所示的酰胺类化合物具有显著病害抑制效果,尤其对黄瓜白粉病、黄瓜霜霉病、大豆锈病、水稻纹枯病、马铃薯晚疫病菌具有很好的防治效果,本发明化合物活性显著优于化合物KC1、KC2和KC3,具有优异的植物病害防治效果。
生测实施例6:
在本实施例中验证含有效成份化合物2与戊唑醇的组合物对小麦白粉病(Blumeria graminis)具有增效作用。
(1)目的:有效成份化合物2与戊唑醇的组合物对小麦白粉病的盆栽防效,并评价含有效成份化合物2与戊唑醇的联合作用类型。
(2)方法:喷雾法
①试材准备:用6cm盆钵播种小麦,每盆钵15~20粒,待幼苗长至1~2叶期,从中挑选长势一致的小麦苗,用油性记号笔写上标签编号,插入盆内,按顺序排放,供试验用。每处理3个重复。
②药剂配置:药剂名称:化合物2,戊唑醇,均为原药。母液配制:按试验设计的比例和剂量,称取一定量的原药,用N,N-二甲基甲酰胺(DMF)溶解,之后加0.1%吐温80水配制成一定浓度的母液。药液配制:每个配比设5~7个剂量,按照试验设计,依次用母液稀释至试验剂量。
③药剂处理:采用叶面喷雾的方法施药,将配置好的药剂均匀喷施于小麦苗上,自然阴干。施药时同种药剂从低浓度到高浓度依次施药。设不含药剂的空白对照。
④接种病原菌:药剂处理后24小时,将发病小麦叶片上产生的白粉病菌孢子均匀抖落接种于盆栽小麦苗上,置于20~25℃培养室内培养。
⑤结果调查:待对照充分发病后,进行防病效果评估。结果调查参照美国植病学会编写的《A Manual of Assessment Keys for Plant Diseases》,用100~0来表示,以“100”级代表无病和“0”级代表最严重的发病程度。
⑥数据处理:利用DPS(v16.05)统计分析软件,计算各药剂的EC50值。
根据Wadley法,用增效系数(SR)来评价组合物的增效效果,即SR<0.5为拮抗作用,0.5≤SR≤1.5为相加作用,SR>1.5为增效作用。增效系数(SR)按以下方式计算:
SR=EC50(th)/EC50(ob)
式中:EC50(th)—组合物的EC50理论值,单位为毫克每升(mg/L);
EC50(ob)—组合物的EC50实测值,单位为毫克每升(mg/L);
a/b—单剂在组合物中的比例数值;
EC(A)50—组合物中A的EC50值,单位为毫克每升(mg/L);
EC(B)50—组合物中B的EC50值,单位为毫克每升(mg/L);
(3)结果见表17。
表17
(4)组合物的联合作用评价:结果表明,化合物2和戊唑醇对小麦白粉病均有较好活性;化合物和戊唑醇复配,1:100~100:1各个配比的增效系数为1.03~2.47,均表现为相加或增效作用;在配比1:25~10:1之间表现为增效作用,配比1:10~10:1表现为显著增效作用(SR>2.0)。
生测实施例7:
在本实施例中验证含有效成份化合物95和丙硫菌唑的组合物对小麦赤霉病(Fusarium graminearum)具有增效作用
(1)目的:测试含有效成份化合物95和丙硫菌唑的组合物对小麦赤霉病的离体活性,并评价含有效成份化合物95和丙硫菌唑的联合作用类型。
(2)方法:菌丝生长速率法
①试材准备:在马铃薯葡萄糖琼脂(PDA)培养基平板上提前2~3天活化小麦赤霉病菌,于25℃生化培养箱中黑暗培养,待用。
②药剂配置:药剂名称:化合物95,丙硫菌唑,均为原药。
母液配制:按试验设计的比例和剂量,称取一定量的原药,用N,N-二甲基甲酰胺(DMF)溶解,之后加0.1%吐温80水配制成一定浓度的母液。
药液配制:每个配比设5~7个剂量,按照试验设计,依次用母液稀释至试验剂量。
③药剂处理:在无菌操作条件下,取稀释好的药剂1mL,与49mL冷却至70℃左右的无菌培养基混合摇匀(溶解好的培养基置于70℃电热恒温鼓风干燥箱中保温),将含药培养基等量倒入3个直径为9cm的培养皿中,制成相应系列浓度的含药平板。
④接种病原菌:用无菌专用打孔器制作病原菌菌饼(直径5mm),自菌落边缘切取菌饼,用接种器将菌饼接种于各含药平板中央,菌丝面朝下,盖上皿盖,置于25℃培养箱中黑暗培养60h左右。
⑤结果调查:待对照菌落长至6cm左右时进行调查,用卡尺测量菌落直径,每个抑菌圈用十字交叉法垂直测量直径各一次。
⑥数据处理:根据调查结果,按以下两个公式计算各处理浓度对病菌的菌丝生长抑制率。
菌落增长直径(cm)=菌落直径–菌饼直径(0.5)
菌丝生长抑制率(%)=(空白对照菌落增长直径–药剂处理菌落增长直径)/空白对照菌落增长直径×100%
用DPS(v16.05)统计分析软件,计算各药剂的EC50值。
增效效果评价方法参照生测实施例1。
(3)结果见表18所示
表18
(4)组合物的联合作用评价:结果表明,化合物95和丙硫菌唑对小麦赤霉病菌均有较好活性;化合物和丙硫菌唑复配,1:80~80:1各个配比的增效系数为0.91~2.54,均表现为相加或增效作用;在配比1:10~10:1之间表现为增效作用,配比1:5~5:1表现为显著增效作用(SR>2.0)。
生测实施例8:
含有效成份化合物104和嘧菌酯的组合物对马铃薯晚疫病(Phytophthorainfestans)具有增效作用
(1)目的:测试含有效成份化合物104和嘧菌酯的组合物对马铃薯晚疫病的离体活性,并评价含有效成份化合物104和嘧菌酯的联合作用类型。
(2)方法:菌丝生长速率法
①试材准备:在黑麦蔗糖琼脂(RSA)培养基平板上提前活化马铃薯晚疫病菌,于23℃生化培养箱中黑暗培养,待用。
②药剂配置:药剂名称:化合物104,嘧菌酯,均为原药。母液配制:按试验设计的比例和剂量,称取一定量的原药,用N,N-二甲基甲酰胺(DMF)溶解,之后加0.1%吐温80水配制成一定浓度的母液。药液配制:每个配比设5~7个剂量,按照试验设计,依次用母液配置为试验剂量的50倍。
③药剂处理:在无菌操作条件下,取配置好的药剂1mL,与49mL冷却至70℃左右的无菌培养基混合摇匀(溶解好的培养基置于70℃电热恒温鼓风干燥箱中保温),将含药培养基等量倒入3个直径为9cm的培养皿中,制成相应系列浓度的含药平板。
④接种病原菌:用无菌专用打孔器制作病原菌菌饼(直径5mm),自菌落边缘切取菌饼,用接种器将菌饼接种于各含药平板中央,菌丝面朝下,盖上皿盖,置于23℃培养箱中黑暗培养5~7d。
⑤结果调查:待对照菌落长至6cm左右时进行调查,用卡尺测量菌落直径,每个抑菌圈用十字交叉法垂直测量直径各一次。
⑥数据处理:根据调查结果,按以下两个公式计算各处理浓度对病菌的菌丝生长抑制率。
菌落增长直径(cm)=菌落直径–菌饼直径(0.5)
菌丝生长抑制率(%)=(空白对照菌落增长直径–药剂处理菌落增长直径)/空白对照菌落增长直径×100%
用DPS(v16.05)统计分析软件,计算各药剂的EC50值。
增效效果评价方法参照生测实施例1。
(3)结果见表19。
表19
(4)组合物的联合作用评价:结果表明,化合物104和嘧菌酯对马铃薯晚疫病菌均有较好活性;化合物和嘧菌酯复配,1:100~100:1各个配比的增效系数为0.56~2.24,均表现为相加或增效作用;在配比1:8~4:1之间表现为增效作用。
生测实施例9:
在本实施例中验证含有效成份化合物84和肟菌酯的组合物对水稻稻瘟病(Pyricularia oryzae)具有增效作用
(1)目的:测试含有效成份化合物84与肟菌酯的组合物对水稻稻瘟病的盆栽防效,并评价含有效成份酰胺化合物84与肟菌酯的联合作用类型。
(2)方法:喷雾法
①试材准备:水稻催芽露白后,用6cm盆钵播种水稻,每盆钵15粒左右,待幼苗长至2~3叶期,从中挑选长势一致的水稻苗,用油性记号笔写上标签编号,插入盆内,按顺序排放,供试验用。每处理3个重复。提前活化水稻稻瘟病菌,待产孢后备用。
②药剂配置:药剂名称:化合物84,肟菌酯,均为原药。母液配制:按试验设计的比例和剂量,称取一定量的原药,用N,N-二甲基甲酰胺(DMF)溶解,之后加0.1%吐温80水配制成一定浓度的母液。药液配制:每个配比设5~7个剂量,按照试验设计,依次用母液稀释至试验剂量,每处理重复3次。
③药剂处理:采用叶面喷雾的方法施药,将配置好的药剂均匀喷施于水稻苗上,自然阴干。施药时同种药剂从低浓度到高浓度依次施药。设不含药剂的空白对照。
④接种病原菌:药剂处理后24小时,将制作好的水稻稻瘟病菌孢子悬浮液,均匀喷施于施药后的水稻叶片上。接种后移至保湿箱中(相对湿度100%,保持叶面有结露,温度26℃左右)黑暗条件下保湿培养24h。然后在26℃左右,相对湿度85%~90%的保湿箱中光照培养5~7d。
⑤结果调查:对照充分发病后,进行防病效果评估。结果调查参照美国植病学会编写的《A Manual of Assessment Keys for Plant Diseases》,用100~0来表示,以“100”级代表无病和“0”级代表最严重的发病程度。
⑥数据处理:利用DPS(v16.05)统计分析软件,计算各药剂的EC50值。
增效效果评价方法参照生测实施例1。
(3)结果见表20。
表20
(4)组合物的联合作用评价:结果表明,化合物84和肟菌酯对水稻稻瘟病均有较好活性;化合物84和肟菌酯复配,1:100~100:1各个配比的增效系数为0.96~2.40,均表现为相加或增效作用;在配比1:10~25:1之间表现为增效作用,配比1:1~10:1表现为显著增效作用(SR>2.0)。
生测实施例10:
在本实施例中验证含有效成份化合物96和井冈霉素的组合物对水稻纹枯病(Rhizoctonia solani)具有增效作用
(1)目的:测试含有效成份化合物96和井冈霉素的组合物对水稻纹枯病的盆栽防效,并评价含有效成份化合物96和井冈霉素的联合作用类型。
(2)方法:喷雾法
①试材准备:水稻催芽露白后,用6cm盆钵播种水稻,每盆钵20粒左右,待幼苗长至1~2叶期,从中挑选长势一致的水稻苗,用油性记号笔写上标签编号,插入盆内,按顺序排放,供试验用。每处理3个重复。
②药剂配置:药剂名称:化合物96,井冈霉素,均为原药。母液配制:按试验设计的比例和剂量,称取一定量的原药,用N,N-二甲基甲酰胺(DMF)溶解,之后加0.1%吐温80水配制成一定浓度的母液。药液配制:每个配比设5~7个剂量,按照试验设计,依次用母液稀释至试验剂量。
③药剂处理:采用叶面喷雾的方法施药,将配置好的药剂均匀喷施于水稻苗上,自然阴干。施药时同种药剂从低浓度到高浓度依次施药。设不含药剂的空白对照。
④接种病原菌:药剂处理后24小时,用镊子将培养好的水稻纹枯病菌菌丝块接种于水稻茎基部,接种后移至25℃~26℃,相对湿度85%~90%的保湿箱中光照培养5d左右。
⑤结果调查:待对照充分发病后,进行防病效果评估。结果调查参照美国植病学会编写的《A Manual of Assessment Keys for Plant Diseases》,用100~0来表示,以“100”级代表无病和“0”级代表最严重的发病程度。
⑥数据处理:利用DPS(v16.05)统计分析软件,计算各药剂的EC50值。
增效效果评价方法参照生测实施例1。
(3)结果见表21。
表21
(4)组合物的联合作用评价:结果表明,化合物96和井冈霉素对水稻纹枯病均有较好活性;化合物和井冈霉素复配,1:100~100:1各个配比的增效系数为0.82~1.61,均表现为相加或增效作用;在配比1:1~1:5之间表现为增效作用。
生测实施例11:
在本实施例中验证含有效成份化合物3和噻呋酰胺的组合物对水稻纹枯病(Rhizoctonia solani)具有增效作用
(1)目的:测试含有效成份化合物3和噻呋酰胺的组合物对水稻纹枯病菌的离体活性,并评价含有效成份化合物3和噻呋酰胺的联合作用类型。
(2)方法:菌丝生长速率法
①试材准备:在马铃薯葡萄糖琼脂(PDA)培养基平板上提前2~3天活化水稻纹枯病菌,于25℃生化培养箱中黑暗培养,待用。
②药剂配置:药剂名称:化合物3,噻呋酰胺,均为原药。母液配制:按试验设计的比例和剂量,称取一定量的原药,用N,N-二甲基甲酰胺(DMF)溶解,之后加0.1%吐温80水配制成一定浓度的母液。药液配制:每个配比设5~7个剂量,按照试验设计,依次用母液配置为试验剂量的50倍。
③药剂处理:在无菌操作条件下,取配置好的药剂1mL,与49mL冷却至70℃左右的无菌培养基混合摇匀(溶解好的培养基置于70℃电热恒温鼓风干燥箱中保温),将含药培养基等量倒入3个直径为9cm的培养皿中,制成相应系列浓度的含药平板。
④接种病原菌:用无菌专用打孔器制作病原菌菌饼(直径5mm),自菌落边缘切取菌饼,用接种器将菌饼接种于各含药平板中央,菌丝面朝下,盖上皿盖,置于23℃培养箱中黑暗培养40h左右。
⑤结果调查:待对照菌落长至6cm左右时进行调查,用卡尺测量菌落直径,每个抑菌圈用十字交叉法垂直测量直径各一次。
⑥数据处理:根据调查结果,按以下两个公式计算各处理浓度对病菌的菌丝生长抑制率。
菌落增长直径(cm)=菌落直径–菌饼直径(0.5)
菌丝生长抑制率(%)=(空白对照菌落增长直径–药剂处理菌落增长直径)/空白对照菌落增长直径×100%
用DPS(v16.05)统计分析软件,计算各药剂的EC50值。
增效效果评价方法参照生测实施例1。
(3)结果见表22
表22
(4)组合物的联合作用评价:
结果表明,化合物3和噻呋酰胺对水稻纹枯病菌均有较好活性;化合物和噻呋酰胺复配,1:100~100:1各个配比的增效系数为0.77~2.48,均表现为相加或增效作用;在配比1:10~2.5:1之间表现为增效作用,配比2.5:1~1:2.5表现为显著增效作用(SR>2.0)。
生测实施例12:
在本实施例中验证含有效成份化合物59和百菌清的组合物对苹果褐斑病(Marssonina coronaria)具有增效作用
(1)目的:测试含有效成份化合物59和百菌清的组合物对苹果褐斑病的离体活性,并评价含有效成份化合物59和百菌清的联合作用类型。
(2)方法:液体振荡培养法
①试材准备:在马铃薯胡萝卜葡萄糖琼脂(PCDA)培养基平板上提前活化苹果褐斑病,于25℃生化培养箱中黑暗培养,待用。
②药剂配置:药剂名称:化合物59,百菌清,均为原药。母液配制:按试验设计的比例和剂量,称取一定量的原药,用N,N-二甲基甲酰胺(DMF)溶解,之后加0.1%吐温80水配制成一定浓度的母液。药液配制:每个配比设5~7个剂量,按照试验设计,依次用母液配置为试验剂量的50倍。
③药剂处理:在无菌操作条件下,取配置好的药剂1mL,与49mL马铃薯胡萝卜葡萄糖培养液混合摇匀,每处理3个重复,设不加药剂的空白对照。
④接种病原菌:将苹果褐斑病菌孢子悬浮液(1~5﹡105个孢子/mL)1mL加入含药的培养液中,25℃,150rpm振荡培养。
⑤结果调查:振荡培养约14d后,用滤纸过滤培养液,80℃烘干至恒重后称量菌丝干重。
⑥数据处理:根据调查结果,按以下公式计算各处理浓度对病菌的菌丝生长抑制率。
菌丝生长抑制率(%)=(空白对照菌丝干重–药剂处理菌丝干重)/空白对照菌丝干重×100%
用DPS(v16.05)统计分析软件,计算各药剂的EC50值。
增效效果评价方法参照生测实施例1。
(3)结果见表23。
表23
(4)组合物的联合作用评价:结果表明,化合物59和百菌清对苹果褐斑病均有较好活性;化合物和百菌清复配,1:64~64:1各个配比的增效系数为0.83~2.32,均表现为相加或增效作用;在配比1:8~2:1之间表现为增效作用,配比1:2~2:1表现为显著增效作用(SR>2.0)。
生测实施例13:
在本实施例中验证含有效成份化合物60和甲基硫菌灵的组合物对黄瓜炭疽病(Erysiphe cichoracearum)具有增效作用
(1)目的:测试含有效成份化合物60与甲基硫菌灵的组合物对黄瓜炭疽病的盆栽防效,并评价含有效成份化合物60与甲基硫菌灵的联合作用类型。
(2)方法:喷雾法
①试材准备:黄瓜催芽露白后,用6cm盆钵播种黄瓜,每盆钵1粒,待幼苗长至1~2叶期,从中挑选长势一致的黄瓜苗,用油性记号笔写上标签编号,插入盆内,按顺序排放,供试验用。每处理3个重复。
②药剂配置:药剂名称:化合物60,甲基硫菌灵,均为原药。母液配制:按试验设计的比例和剂量,称取一定量的原药,用N,N-二甲基甲酰胺(DMF)溶解,之后加0.1%吐温80水配制成一定浓度的母液。药液配制:每个配比设5~7个剂量,按照试验设计,依次用母液稀释至试验剂量。
③药剂处理:采用叶面喷雾的方法施药,将配置好的药剂均匀喷施于黄瓜苗上,自然阴干。施药时同种药剂从低浓度到高浓度依次施药。设不含药剂的空白对照。
④接种病原菌:药剂处理后24小时,将黄瓜炭疽病菌孢子悬浮液均匀喷施于施药后的黄瓜叶片,置于保湿室内,25℃,100%RH,保湿培养24h后,置于培养室,25℃常规培养。
⑤结果调查:待对照充分发病后进行防病效果评估。结果调查参照美国植病学会编写的《A Manual of Assessment Keys for Plant Diseases》,用100~0来表示,以“100”级代表无病和“0”级代表最严重的发病程度。
⑥数据处理:利用DPS(v16.05)统计分析软件,计算各药剂的EC50值。
(3)结果见表24。
表24
(4)组合物的联合作用评价:结果表明,化合物60与甲基硫菌灵对黄瓜炭疽病有较好防效,化合物60和甲基硫菌灵复配,1:100~100:1各个配比的增效系数为0.71~2.21,均表现为相加或增效作用;在配比1:1~25:1之间表现为增效作用,配比5:1~10:1表现为显著增效作用(SR>2.0)。
生测实施例14:
在本实施例中验证含有效成份化合物64和啶酰菌胺的组合物对葡萄灰霉病(Botrytis cinerea)具有增效作用
(1)目的:测试含有效成份化合物64和啶酰菌胺的组合物对葡萄灰霉病菌的离体活性,并评价含有效成份化合物64和啶酰菌胺的联合作用类型。
(2)方法:菌丝生长速率法
①试材准备:在马铃薯葡萄糖琼脂(PDA)培养基平板上提前2~3天活化葡萄灰霉病,于22℃生化培养箱中光照培养,待用。
②药剂配置:药剂名称:化合物64,啶酰菌胺,均为原药。
母液配制:按试验设计的比例和剂量,称取一定量的原药,用N,N-二甲基甲酰胺(DMF)溶解,之后加0.1%吐温80水配制成一定浓度的母液。
药液配制:每个配比设5~7个剂量,按照试验设计,依次用母液配置为试验剂量的50倍。
③药剂处理:在无菌操作条件下,取配置好的药剂1mL,与49mL冷却至70℃左右的无菌培养基混合摇匀(溶解好的培养基置于70℃电热恒温鼓风干燥箱中保温),将含药培养基等量倒入3个直径为9cm的培养皿中,制成相应系列浓度的含药平板。
④接种病原菌:用无菌专用打孔器制作病原菌菌饼(直径5mm),自菌落边缘切取菌饼,用接种器将菌饼接种于各含药平板中央,菌丝面朝下,盖上皿盖,置于22℃培养箱中光照培养72h左右。
⑤结果调查:待对照菌落长至6cm左右时进行调查,用卡尺测量菌落直径,每个抑菌圈用十字交叉法垂直测量直径各一次。
⑥数据处理:根据调查结果,按以下两个公式计算各处理浓度对病菌的菌丝生长抑制率。
菌落增长直径(cm)=菌落直径–菌饼直径(0.5)
菌丝生长抑制率(%)=(空白对照菌落增长直径–药剂处理菌落增长直径)/空白对照菌落增长直径×100%
用DPS(v16.05)统计分析软件,计算各药剂的EC50值。
增效效果评价方法参照生测实施例1。
(3)结果见表25。
表25
(4)组合物的联合作用评价:结果表明,化合物64和啶酰菌胺对葡萄灰霉病菌均有较好活性;化合物和啶酰菌胺复配,1:80~80:1各个配比的增效系数为0.95~2.15,均表现为相加或增效作用;在配比1:5~1:1之间表现为增效作用,配比1:1表现为显著增效作用(SR>2.0)。
生测实施例15:
在本实施例中验证含有效成份化合物100和氟唑活化酯的组合物对黄瓜白粉病(Erysiphe cichoracearum)具有增效作用
(1)目的:测试含有效成份化合物100和氟唑活化酯的组合物对黄瓜白粉病的盆栽防效,并评价含有效成份化合物100和氟唑活化酯的联合作用类型。
(2)方法:喷雾法
①试材准备:黄瓜催芽露白后,用6cm盆钵播种黄瓜,每盆钵1粒,待幼苗长至1~2叶期,从中挑选长势一致的黄瓜苗,用油性记号笔写上标签编号,插入盆内,按顺序排放,供试验用。每处理3个重复。
②药剂配置:药剂名称:化合物100,氟唑活化酯,均为原药。母液配制:按试验设计的比例和剂量,称取一定量的原药,用N,N-二甲基甲酰胺(DMF)溶解,之后加0.1%吐温80水配制成一定浓度的母液。药液配制:每个配比设5~7个剂量,按照试验设计,依次用母液稀释至试验剂量。
③药剂处理:采用叶面喷雾的方法施药,将配置好的药剂均匀喷施于黄瓜苗上,自然阴干。施药时同种药剂从低浓度到高浓度依次施药。设不含药剂的空白对照。
④接种病原菌:药剂处理后24小时,将发病黄瓜叶片上产生的白粉病菌洗脱下来,制成孢子悬浮液,均匀喷施于施药后的黄瓜叶片,置于25℃左右培养室内培养。
⑤结果调查:待对照充分发病后,进行防病效果评估。结果调查参照美国植病学会编写的《A Manual of Assessment Keys for Plant Diseases》,用100~0来表示,以“100”级代表无病和“0”级代表最严重的发病程度。
⑥数据处理:利用DPS(v16.05)统计分析软件,计算各药剂的EC50值。
增效效果评价方法参照生测实施例1。
(3)结果见表26。
表26
(4)组合物的联合作用评价:结果表明,化合物100和氟唑活化酯对黄瓜白粉病均有较好活性;化合物和氟唑活化酯复配,1:10~10:1各个配比的增效系数为0.82~1.68,均表现为相加或增效作用;在配比1:1~1:5表现为显著的增效作用。
本发明通过上述实施例来说明本发明的含有酰胺类化合物的药物组合物及其应用,但本发明并不局限于上述实施例,即不意味着本发明必须依赖上述实施例才能实施。所属技术领域的技术人员应该明了,对本发明的任何改进,对本发明产品各原料的等效替换及辅助成分的添加、具体方式的选择等,均落在本发明的保护范围和公开范围之内。
Claims (10)
1.一种含有酰胺类化合物的药物组合物,其特征在于,所述药物组合物包括有效成分A和有效成分B,所述有效成分A为具有式I所示结构的酰胺类化合物,所述有效成分B包括其他杀菌剂、杀虫剂或杀螨剂中任意一种或两种的组合;
X选自C2-C12烷基、C1-C12烷氧基、C1-C12卤代烷氧基、C2-C12烯基、C2-C12卤代烯基、C2-C12炔基、C2-C12卤代炔基、C3-C8环烷基、C3-C8卤代环烷基、C1-C12烷基亚磺酰基、C1-C12卤代烷基亚磺酰基、C1-C12烷基磺酰基或C1-C12卤代烷基磺酰基;Y选自C1-C6烷基、C1-C6卤代烷基、C1-C6烷氧基、C1-C6卤代烷氧基、C2-C4烯基、C2-C4卤代烯基、C2-C4炔基、C2-C4卤代炔基、C3-C8环烷基、C3-C8卤代环烷基、C1-C6烷基亚磺酰基、C1-C6卤代烷基亚磺酰基、C1-C6烷基磺酰基或C1-C6卤代烷基磺酰基;R1选自氢、卤素、氰基、硝基、取代或未取代的烷基、取代或未取代的烷氧基、取代或未取代的烯基、取代或未取代的炔基、取代或未取代的环烷基、取代或未取代的烷基亚磺酰基、取代或未取代的烷基磺酰基;W表示氧原子或硫原子,m为0-4的整数。
2.根据权利要求1所述的含有酰胺类化合物的药物组合物,其特征在于,R1选自氢、卤素、氰基、硝基、C1-C6烷基、C1-C6卤代烷基、C1-C6烷氧基、C1-C6卤代烷氧基、C2-C4烯基、C2-C4卤代烯基、C2-C4炔基、C2-C4卤代炔基、C3-C8环烷基、C3-C8卤代环烷基、C1-C6烷基亚磺酰基、C1-C6卤代烷基亚磺酰基、C1-C6烷基磺酰基或C1-C6卤代烷基磺酰基;
优选地,R2选自C1-C6烷基或C1-C6卤代烷基;
优选地,在式I中,Q选自R2选自甲基、乙基、异丙基、二氟甲基、三氟甲基或2-氟乙基;X选自C2-C12烷基;Y选自C1-C6烷基;R1选自氢;m为0-4的整数;W表示氧原子或硫原子;
进一步优选地,所述酰胺类化合物为具有如下编号的化合物中的任意一种:
3.根据权利要求1或2所述的含有酰胺类化合物的药物组合物,其特征在于,所述有效成分B选自杀菌剂、杀虫剂、杀螨剂中的任意一种或至少两种的组合;
优选地,所述杀菌剂选自环丙唑醇、丙硫菌唑、苯醚甲环唑、氟环唑、烯唑醇、腈苯唑、氟硅唑、粉唑醇、戊唑醇、己唑醇、腈菌唑、戊菌唑、丙环唑、四氟醚唑、三唑醇、联苯三唑醇、三唑酮、嘧菌酯、醚菌酯、肟菌酯、啶氧菌酯、吡唑醚菌酯、氟嘧菌酯、肟醚菌胺、丁香菌酯、烯肟菌酯、烯肟菌胺或唑菌酯、氟唑菌酰胺、联苯吡菌胺、苯丙烯氟菌唑、氟唑菌酰羟胺、甲霜灵、精甲霜灵、氟酰胺、噻呋酰胺、缬霉威、噻唑菌胺、双炔酰菌胺、啶酰菌胺、氟吡菌胺、稻瘟酰胺、氟吡菌酰胺、萎锈灵、噻菌灵、抑霉唑、咪鲜胺、稻瘟酯、腈霜唑、氟菌唑、腐霉利、异菌脲、乙烯菌核利、克菌丹、菌核净、霜霉威盐酸盐、乙霉威、多菌灵、苯菌灵、甲基硫菌灵、井冈霉素、中生菌素、硫酸链霉素、多抗霉素、春雷霉素、梧宁霉素、噁霉灵、噁霜灵、烯酰吗啉、氟吗啉、十三吗啉、嘧菌环胺、嘧霉胺、乙嘧酚、二氰蒽醌、代森联、福美双、代森锌、代森锰、代森锰锌、丙森锌、敌瘟磷、三乙膦酸铝、百菌清、稻瘟灵、三环唑、五氯硝基苯、噁唑菌酮、霜脲腈、咯菌腈、敌磺钠、氟啶胺、噻菌铜、氟噻唑吡乙酮、磷酸二氢钾、硫磺、氢氧化铜、活化酯或氟唑活化酯中的任意一种或至少两种的组合;
优选地,所述杀虫剂选自噻虫嗪、吡虫啉、噻虫胺、噻虫啉、啶虫脒、烯啶虫胺、呋虫胺、氟啶虫胺腈、多杀菌素、乙基多杀菌素、毒死蜱、丁硫克百威、丙硫克百威、氟虫腈、乙虫腈、高效氯氟氰菊酯、氯菊酯、甲氰菊酯、醚菊酯、溴氰菊酯、氯氰菊酯、氟氯氰菊酯、联苯菊酯、顺式氰戊菊酯、顺式氯氰菊酯、除虫菊素、阿维菌素、甲氨基阿维菌素苯甲酸盐、吡丙醚、苯氧威、吡蚜酮、氟啶虫酰胺、氟虫脲、虱螨脲、双氟虫脲、氟啶脲、除虫脲、氟环脲、氟铃脲、氟酰脲、多氟脲、杀铃脲、环虫酰肼、甲氧虫酰肼、虫酰肼、氯虫酰肼、唑虫酰胺、茚虫威、氰氟虫腙、螺虫乙酯、氯虫苯甲酰胺、氟苯虫酰胺、溴氰虫酰胺、环溴虫酰胺、四氯虫酰胺、tetraniliprole或broflanilide中的任意一种或至少两种的组合;
优选地,所述杀螨剂选自四螨嗪、噻螨酮、乙螨唑、唑螨醚、唑螨酯、嘧螨醚、哒螨灵、吡螨胺、联苯肼酯、克螨特、苯丁锡、丁氟螨酯、腈吡螨酯、双甲脒、灭螨醌、喹螨醚、三唑锡、三环锡、溴螨酯、氟螨嗪、嘧螨酯、磺胺螨酯、螺螨酯或螺甲螨酯中的任意一种或至少两种的组合。
4.根据权利要求1-3中任一项所述的含有酰胺类化合物的药物组合物,其特征在于,所述有效成分B选自丙硫菌唑、苯醚甲环唑、氟环唑、戊唑醇、己唑醇、腈菌唑、三唑酮、嘧菌酯、肟菌酯、啶氧菌酯、吡唑醚菌酯、甲霜灵、噻呋酰胺、双炔酰菌胺、啶酰菌胺、氟唑菌酰羟胺、氟吡菌胺、稻瘟酰胺、氟吡菌酰胺、咪鲜胺、霜霉威盐酸盐、多菌灵、甲基硫菌灵、井冈霉素、春雷霉素、烯酰吗啉、氟吗啉、乙嘧酚、福美双、代森锌、代森锰锌、三乙膦酸铝、百菌清、稻瘟灵、咯菌腈、氟啶胺、氟唑活化酯、噻虫嗪、吡虫啉、噻虫胺、多杀菌素、乙基多杀菌素、毒死蜱、氟虫腈、乙虫腈、高效氯氟氰菊酯、醚菊酯、溴氰菊酯、氟氯氰菊酯、阿维菌素、呋虫胺、啶虫脒、甲氨基阿维菌素苯甲酸盐、吡蚜酮、氟啶虫酰胺、氯虫苯甲酰胺或溴氰虫酰胺中的任意一种或至少两种的组合;
进一步优选地,所述有效成分B选自丙硫菌唑、苯醚甲环唑、氟环唑、戊唑醇、己唑醇、腈菌唑、三唑酮、嘧菌酯、肟菌酯、啶氧菌酯、吡唑醚菌酯、噻呋酰胺、啶酰菌胺、稻瘟酰胺、氟吡菌酰胺、咪鲜胺、多菌灵、甲基硫菌灵、井冈霉素、春雷霉素、乙嘧酚、福美双、代森锰锌、百菌清、稻瘟灵、咯菌腈、噻虫嗪、吡虫啉、噻虫胺、呋虫胺、氟虫腈、氯虫苯甲酰胺或溴氰虫酰胺中的任意一种或至少两种的组合。
5.根据权利要求1-4中任一项所述的含有酰胺类化合物的药物组合物,其特征在于,所述有效成分A和有效成分B的重量比是200:1-1:200;
优选地,当所述含有酰胺类化合物的药物组合物中有效成分B为环丙唑醇、丙硫菌唑、苯醚甲环唑、氟环唑、烯唑醇、氟硅唑、粉唑醇、戊唑醇、己唑醇、腈菌唑、戊菌唑、丙环唑或四氟醚唑中的任意一种时,式I所示结构的酰胺类化合物:有效成分B的重量比为50:1-1:50,优选20:1-1:20;
优选地,当所述含有酰胺类化合物的药物组合物中有效成分B为嘧菌酯、醚菌酯、肟菌酯、啶氧菌酯、吡唑醚菌酯或氟嘧菌酯中的任意一种时,式I所示结构的酰胺类化合物:有效成分B的重量比为50:1-1:50,优选20:1-1:20;
优选地,当所述含有酰胺类化合物的药物组合物中有效成分B为氟唑菌酰胺、联苯吡菌胺、苯丙烯氟菌唑、氟唑菌酰羟胺、精甲霜灵、噻呋酰胺、双炔酰菌胺、啶酰菌胺、氟吡菌酰胺或萎锈灵中的任意一种时,式I所示结构的酰胺类化合物:有效成分B的重量比为50:1-1:50,优选20:1-1:20;
优选地,当所述含有酰胺类化合物的药物组合物中有效成分B为噻菌灵、抑霉唑、咪鲜胺、稻瘟酯、腈霜唑或氟菌唑中的任意一种时,式I所示结构的酰胺类化合物:有效成分B的重量比为10:1-1:150,优选5:1-1:100;
优选地,当所述含有酰胺类化合物的药物组合物中有效成分B为腐霉利、异菌脲、乙烯菌核利、克菌丹或菌核净中的任意一种时,式I所示结构的酰胺类化合物:有效成分B的重量比为1:1-1:150,优选1:1-1:100;
优选地,当所述含有酰胺类化合物的药物组合物中有效成分B为霜霉威盐酸盐、乙霉威、多菌灵、苯菌灵或甲基硫菌灵中的任意一种时,式I所示结构的酰胺类化合物:有效成分B的重量比为10:1-1:50,优选5:1-1:20;
优选地,当所述含有酰胺类化合物的药物组合物中有效成分B为井冈霉素、中生菌素、硫酸链霉素、多抗霉素、春雷霉素或梧宁霉素中的任意一种时,式I所示结构的酰胺类化合物:有效成分B的重量比为50:1-1:50,优选10:1-1:20;
优选地,当所述含有酰胺类化合物的药物组合物中有效成分B为百菌清时,式I所示结构的酰胺类化合物:有效成分B的重量比为1:1-1:150,优选1:1-1:100;
优选地,当所述含有酰胺类化合物的药物组合物中有效成分B为咯菌腈时,式I所示结构的酰胺类化合物:有效成分B的重量比为50:1-1:50,优选10:1-1:20;
优选地,当所述含有酰胺类化合物的药物组合物中有效成分B为三环唑时,式I所示结构的酰胺类化合物:有效成分B的重量比为50:1-1:50,优选10:1-1:20;
优选地,当所述含有酰胺类化合物的药物组合物中有效成分B为稻瘟灵时,式I所示结构的酰胺类化合物:有效成分B的重量比为10:1-1:150,优选5:1-1:100;
优选地,当所述含有酰胺类化合物的药物组合物中有效成分B为代森锰锌时,式I所示结构的酰胺类化合物:有效成分B的重量比为1:1-1:150,优选1:1-1:100;
优选地,当所述含有酰胺类化合物的药物组合物中有效成分B为噻虫嗪、吡虫啉、噻虫胺或呋虫胺中的任意一种时,式I所示结构的酰胺类化合物:有效成分B的重量比为50:1-1:50,优选10:1-1:20;
优选地,当所述含有酰胺类化合物的药物组合物中有效成分B为氟虫腈,式I所示结构的酰胺类化合物:有效成分B的重量比为50:1-1:50,优选20:1-1:20;
优选地,当所述含有酰胺类化合物的药物组合物中有效成分B为氯虫苯甲酰胺、氟苯虫酰胺或溴氰虫酰胺中的任意一种,式I所示结构的酰胺类化合物:有效成分B的重量比为50:1-1:50,优选20:1-1:20。
6.根据权利要求1-5中任一项所述的含有酰胺类化合物的药物组合物在农业、林业、园艺上防治植物病害或虫害中的应用。
7.根据权利要求1-5中任一项所述的含有酰胺类化合物的药物组合物在植物、作物或花卉的种子处理中的应用。
8.一种药物制剂,其特征在于,所述药物制剂包括如上所述的含有酰胺类化合物的药物组合物和农药学上可接受的载体;
优选地,所述农药制剂中,含有酰胺类化合物的药物组合物的重量百分比为1-99%;
优选地,所述药物制剂的剂型为溶液剂、悬浮剂、乳油剂、粉剂、乳剂、颗粒剂或种衣剂。
9.一种防治植物病害的方法,其特征在于,所述方法为:向需要控制的植物病害或其生长的介质上施用有效剂量的如权利要求1-5中任一项所述的含有酰胺类化合物的药物组合物。
10.根据权利要求9所述的方法,其特征在于,所述有效剂量为每公顷10-1000g,优选每公顷20-500g。
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