CN86100254A - 制备叔胺类化合物的方法 - Google Patents
制备叔胺类化合物的方法 Download PDFInfo
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- CN86100254A CN86100254A CN198686100254A CN86100254A CN86100254A CN 86100254 A CN86100254 A CN 86100254A CN 198686100254 A CN198686100254 A CN 198686100254A CN 86100254 A CN86100254 A CN 86100254A CN 86100254 A CN86100254 A CN 86100254A
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- Prior art keywords
- alkyl
- compound
- hydrogen
- phenyl
- contain
- Prior art date
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- 238000000034 method Methods 0.000 title claims description 42
- -1 tertiary amine compounds Chemical class 0.000 title claims description 27
- 150000001875 compounds Chemical class 0.000 claims abstract description 95
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 38
- 239000002253 acid Substances 0.000 claims abstract description 24
- 239000001257 hydrogen Substances 0.000 claims abstract description 21
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 21
- 150000003839 salts Chemical class 0.000 claims abstract description 19
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 18
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 12
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 11
- 125000000304 alkynyl group Chemical group 0.000 claims abstract description 11
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 11
- 125000005843 halogen group Chemical group 0.000 claims abstract description 11
- 125000003118 aryl group Chemical group 0.000 claims abstract description 8
- 230000015572 biosynthetic process Effects 0.000 claims abstract description 5
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 4
- 125000004104 aryloxy group Chemical group 0.000 claims abstract description 4
- 230000000855 fungicidal effect Effects 0.000 claims abstract description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 73
- 239000000203 mixture Substances 0.000 claims description 58
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 58
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 54
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 48
- 125000004432 carbon atom Chemical group C* 0.000 claims description 35
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 33
- 229910052799 carbon Inorganic materials 0.000 claims description 31
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 29
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical class OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 28
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 23
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 claims description 20
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 18
- 150000002148 esters Chemical class 0.000 claims description 17
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 16
- 238000002360 preparation method Methods 0.000 claims description 16
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 15
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 14
- 239000003795 chemical substances by application Substances 0.000 claims description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 13
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 13
- 238000006243 chemical reaction Methods 0.000 claims description 12
- 239000000460 chlorine Substances 0.000 claims description 11
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 10
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
- 229910052801 chlorine Inorganic materials 0.000 claims description 10
- 239000012280 lithium aluminium hydride Substances 0.000 claims description 10
- 150000002431 hydrogen Chemical class 0.000 claims description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 8
- 239000002904 solvent Substances 0.000 claims description 8
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 7
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 7
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 7
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 7
- 229910052794 bromium Inorganic materials 0.000 claims description 7
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 claims description 7
- 150000003053 piperidines Chemical class 0.000 claims description 7
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 6
- 229910000366 copper(II) sulfate Inorganic materials 0.000 claims description 6
- YVPJCJLMRRTDMQ-UHFFFAOYSA-N ethyl diazoacetate Chemical compound CCOC(=O)C=[N+]=[N-] YVPJCJLMRRTDMQ-UHFFFAOYSA-N 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 150000002367 halogens Chemical class 0.000 claims description 6
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 5
- 230000002829 reductive effect Effects 0.000 claims description 5
- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 claims description 5
- 150000001263 acyl chlorides Chemical class 0.000 claims description 4
- 150000001408 amides Chemical class 0.000 claims description 4
- 150000001412 amines Chemical class 0.000 claims description 4
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 claims description 4
- 239000000377 silicon dioxide Substances 0.000 claims description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
- 239000005864 Sulphur Substances 0.000 claims description 3
- 150000001336 alkenes Chemical class 0.000 claims description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 3
- 239000000417 fungicide Substances 0.000 claims description 3
- 125000005905 mesyloxy group Chemical group 0.000 claims description 3
- 230000002371 mycocidal effect Effects 0.000 claims description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
- 125000004193 piperazinyl group Chemical group 0.000 claims description 3
- WIHIUTUAHOZVLE-UHFFFAOYSA-N 1,3-diethoxypropan-2-ol Chemical compound CCOCC(O)COCC WIHIUTUAHOZVLE-UHFFFAOYSA-N 0.000 claims description 2
- OGFAWKRXZLGJSK-UHFFFAOYSA-N 1-(2,4-dihydroxyphenyl)-2-(4-nitrophenyl)ethanone Chemical compound OC1=CC(O)=CC=C1C(=O)CC1=CC=C([N+]([O-])=O)C=C1 OGFAWKRXZLGJSK-UHFFFAOYSA-N 0.000 claims description 2
- HDECRAPHCDXMIJ-UHFFFAOYSA-N 2-methylbenzenesulfonyl chloride Chemical compound CC1=CC=CC=C1S(Cl)(=O)=O HDECRAPHCDXMIJ-UHFFFAOYSA-N 0.000 claims description 2
- IDWRJRPUIXRFRX-UHFFFAOYSA-N 3,5-dimethylpiperidine Chemical compound CC1CNCC(C)C1 IDWRJRPUIXRFRX-UHFFFAOYSA-N 0.000 claims description 2
- UTBULQCHEUWJNV-UHFFFAOYSA-N 4-phenylpiperidine Chemical compound C1CNCCC1C1=CC=CC=C1 UTBULQCHEUWJNV-UHFFFAOYSA-N 0.000 claims description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 2
- PHSPJQZRQAJPPF-UHFFFAOYSA-N N-alpha-Methylhistamine Chemical compound CNCCC1=CN=CN1 PHSPJQZRQAJPPF-UHFFFAOYSA-N 0.000 claims description 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Natural products P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims description 2
- 150000001350 alkyl halides Chemical class 0.000 claims description 2
- POULHZVOKOAJMA-UHFFFAOYSA-M dodecanoate Chemical compound CCCCCCCCCCCC([O-])=O POULHZVOKOAJMA-UHFFFAOYSA-M 0.000 claims description 2
- 230000002140 halogenating effect Effects 0.000 claims description 2
- 229940070765 laurate Drugs 0.000 claims description 2
- 229910052744 lithium Inorganic materials 0.000 claims description 2
- 239000011777 magnesium Substances 0.000 claims description 2
- 229910052749 magnesium Inorganic materials 0.000 claims description 2
- YZTJYBJCZXZGCT-UHFFFAOYSA-N phenylpiperazine Chemical compound C1CNCCN1C1=CC=CC=C1 YZTJYBJCZXZGCT-UHFFFAOYSA-N 0.000 claims description 2
- UXCDUFKZSUBXGM-UHFFFAOYSA-N phosphoric tribromide Chemical compound BrP(Br)(Br)=O UXCDUFKZSUBXGM-UHFFFAOYSA-N 0.000 claims description 2
- 229910000073 phosphorus hydride Inorganic materials 0.000 claims description 2
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 claims description 2
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 claims description 2
- VUNPWIPIOOMCPT-UHFFFAOYSA-N piperidin-3-ylmethanol Chemical compound OCC1CCCNC1 VUNPWIPIOOMCPT-UHFFFAOYSA-N 0.000 claims description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims description 2
- 125000005424 tosyloxy group Chemical group S(=O)(=O)(C1=CC=C(C)C=C1)O* 0.000 claims description 2
- 150000001721 carbon Chemical group 0.000 claims 7
- 239000003153 chemical reaction reagent Substances 0.000 claims 4
- 238000010931 ester hydrolysis Methods 0.000 claims 1
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 61
- 239000000243 solution Substances 0.000 description 38
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 36
- 239000007788 liquid Substances 0.000 description 32
- 241000196324 Embryophyta Species 0.000 description 27
- 238000001035 drying Methods 0.000 description 23
- 238000003756 stirring Methods 0.000 description 23
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 22
- 239000003921 oil Substances 0.000 description 18
- 238000000605 extraction Methods 0.000 description 17
- 239000011734 sodium Substances 0.000 description 17
- 241000894006 Bacteria Species 0.000 description 16
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 15
- 201000010099 disease Diseases 0.000 description 15
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 15
- 229910052708 sodium Inorganic materials 0.000 description 15
- 239000000470 constituent Substances 0.000 description 14
- 239000003480 eluent Substances 0.000 description 13
- 239000000741 silica gel Substances 0.000 description 13
- 229910002027 silica gel Inorganic materials 0.000 description 13
- 229960001866 silicon dioxide Drugs 0.000 description 13
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
- 238000004440 column chromatography Methods 0.000 description 12
- 241000233866 Fungi Species 0.000 description 11
- 239000003814 drug Substances 0.000 description 11
- 239000011541 reaction mixture Substances 0.000 description 11
- 239000002245 particle Substances 0.000 description 10
- 239000002689 soil Substances 0.000 description 10
- 239000000843 powder Substances 0.000 description 9
- 239000000725 suspension Substances 0.000 description 9
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
- 239000012230 colorless oil Substances 0.000 description 8
- 230000006837 decompression Effects 0.000 description 8
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 8
- 239000004927 clay Substances 0.000 description 7
- 238000005507 spraying Methods 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- 208000031888 Mycoses Diseases 0.000 description 6
- 235000013339 cereals Nutrition 0.000 description 6
- 241000209140 Triticum Species 0.000 description 5
- 235000021307 Triticum Nutrition 0.000 description 5
- 235000009754 Vitis X bourquina Nutrition 0.000 description 5
- 235000012333 Vitis X labruscana Nutrition 0.000 description 5
- 240000006365 Vitis vinifera Species 0.000 description 5
- 235000014787 Vitis vinifera Nutrition 0.000 description 5
- 239000007810 chemical reaction solvent Substances 0.000 description 5
- 150000004696 coordination complex Chemical class 0.000 description 5
- 229940079593 drug Drugs 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 238000002156 mixing Methods 0.000 description 5
- 239000003208 petroleum Substances 0.000 description 5
- XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical compound [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 description 5
- 238000000746 purification Methods 0.000 description 5
- 244000025254 Cannabis sativa Species 0.000 description 4
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
- IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 4
- DPDMMXDBJGCCQC-UHFFFAOYSA-N [Na].[Cl] Chemical compound [Na].[Cl] DPDMMXDBJGCCQC-UHFFFAOYSA-N 0.000 description 4
- 239000013543 active substance Substances 0.000 description 4
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 229960001701 chloroform Drugs 0.000 description 4
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 4
- 239000006185 dispersion Substances 0.000 description 4
- 239000000839 emulsion Substances 0.000 description 4
- 239000003337 fertilizer Substances 0.000 description 4
- 239000000945 filler Substances 0.000 description 4
- 235000019253 formic acid Nutrition 0.000 description 4
- WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 4
- 230000012010 growth Effects 0.000 description 4
- 229940031815 mycocide Drugs 0.000 description 4
- 238000006386 neutralization reaction Methods 0.000 description 4
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 4
- 230000008635 plant growth Effects 0.000 description 4
- 239000005648 plant growth regulator Substances 0.000 description 4
- 229920006395 saturated elastomer Polymers 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 239000000080 wetting agent Substances 0.000 description 4
- RMOGWMIKYWRTKW-UONOGXRCSA-N (S,S)-paclobutrazol Chemical compound C([C@@H]([C@@H](O)C(C)(C)C)N1N=CN=C1)C1=CC=C(Cl)C=C1 RMOGWMIKYWRTKW-UONOGXRCSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- 240000005979 Hordeum vulgare Species 0.000 description 3
- 235000007340 Hordeum vulgare Nutrition 0.000 description 3
- 240000008790 Musa x paradisiaca Species 0.000 description 3
- 235000018290 Musa x paradisiaca Nutrition 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- NWBJYWHLCVSVIJ-UHFFFAOYSA-N N-benzyladenine Chemical compound N=1C=NC=2NC=NC=2C=1NCC1=CC=CC=C1 NWBJYWHLCVSVIJ-UHFFFAOYSA-N 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- 239000005985 Paclobutrazol Substances 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 3
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Natural products C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 3
- DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 3
- 230000001857 anti-mycotic effect Effects 0.000 description 3
- 239000002543 antimycotic Substances 0.000 description 3
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 3
- 239000007859 condensation product Substances 0.000 description 3
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 3
- FPAFDBFIGPHWGO-UHFFFAOYSA-N dioxosilane;oxomagnesium;hydrate Chemical compound O.[Mg]=O.[Mg]=O.[Mg]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O FPAFDBFIGPHWGO-UHFFFAOYSA-N 0.000 description 3
- 239000002270 dispersing agent Substances 0.000 description 3
- 238000006073 displacement reaction Methods 0.000 description 3
- 239000003995 emulsifying agent Substances 0.000 description 3
- 125000001033 ether group Chemical group 0.000 description 3
- 238000003810 ethyl acetate extraction Methods 0.000 description 3
- XPFVYQJUAUNWIW-UHFFFAOYSA-N furfuryl alcohol Chemical compound OCC1=CC=CO1 XPFVYQJUAUNWIW-UHFFFAOYSA-N 0.000 description 3
- 239000008187 granular material Substances 0.000 description 3
- 239000004615 ingredient Substances 0.000 description 3
- 238000011081 inoculation Methods 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- LCPDWSOZIOUXRV-UHFFFAOYSA-N phenoxyacetic acid Chemical class OC(=O)COC1=CC=CC=C1 LCPDWSOZIOUXRV-UHFFFAOYSA-N 0.000 description 3
- 239000001632 sodium acetate Substances 0.000 description 3
- 229960004249 sodium acetate Drugs 0.000 description 3
- 235000017281 sodium acetate Nutrition 0.000 description 3
- 239000004094 surface-active agent Substances 0.000 description 3
- 239000000375 suspending agent Substances 0.000 description 3
- XQTLDIFVVHJORV-UHFFFAOYSA-N tecnazene Chemical group [O-][N+](=O)C1=C(Cl)C(Cl)=CC(Cl)=C1Cl XQTLDIFVVHJORV-UHFFFAOYSA-N 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- JLIDBLDQVAYHNE-YKALOCIXSA-N (+)-Abscisic acid Chemical compound OC(=O)/C=C(/C)\C=C\[C@@]1(O)C(C)=CC(=O)CC1(C)C JLIDBLDQVAYHNE-YKALOCIXSA-N 0.000 description 2
- ASZCVNVMQXNJGH-ZYRRHWMLSA-N (1S,2R,9S,12S)-4,12-dimethyl-13-oxotetracyclo[10.2.1.01,9.03,8]pentadeca-3,5,7-triene-2-carboxylic acid Chemical class Cc1cccc2[C@H]3CC[C@@]4(C)C[C@@]3(CC4=O)[C@@H](C(O)=O)c12 ASZCVNVMQXNJGH-ZYRRHWMLSA-N 0.000 description 2
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- UFHLMYOGRXOCSL-UHFFFAOYSA-N isoprothiolane Chemical compound CC(C)OC(=O)C(C(=O)OC(C)C)=C1SCCS1 UFHLMYOGRXOCSL-UHFFFAOYSA-N 0.000 description 1
- ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 1
- 235000015110 jellies Nutrition 0.000 description 1
- 239000008274 jelly Substances 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 239000003350 kerosene Substances 0.000 description 1
- 235000012204 lemonade/lime carbonate Nutrition 0.000 description 1
- 239000008291 lyophilic colloid Substances 0.000 description 1
- 239000001095 magnesium carbonate Substances 0.000 description 1
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
- 229910000021 magnesium carbonate Inorganic materials 0.000 description 1
- 235000014380 magnesium carbonate Nutrition 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- YKSNLCVSTHTHJA-UHFFFAOYSA-L maneb Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S YKSNLCVSTHTHJA-UHFFFAOYSA-L 0.000 description 1
- 229920000940 maneb Polymers 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- ZWJNEYVWPYIKMB-UHFFFAOYSA-N methfuroxam Chemical compound CC1=C(C)OC(C)=C1C(=O)NC1=CC=CC=C1 ZWJNEYVWPYIKMB-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- CJPQIRJHIZUAQP-UHFFFAOYSA-N methyl N-(2,6-dimethylphenyl)-N-(phenylacetyl)alaninate Chemical compound CC=1C=CC=C(C)C=1N(C(C)C(=O)OC)C(=O)CC1=CC=CC=C1 CJPQIRJHIZUAQP-UHFFFAOYSA-N 0.000 description 1
- CIEXPHRYOLIQQD-UHFFFAOYSA-N methyl N-(2,6-dimethylphenyl)-N-2-furoylalaninate Chemical compound CC=1C=CC=C(C)C=1N(C(C)C(=O)OC)C(=O)C1=CC=CO1 CIEXPHRYOLIQQD-UHFFFAOYSA-N 0.000 description 1
- NCWQJOGVLLNWEO-UHFFFAOYSA-N methylsilicon Chemical compound [Si]C NCWQJOGVLLNWEO-UHFFFAOYSA-N 0.000 description 1
- 239000003094 microcapsule Substances 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- KRTSDMXIXPKRQR-AATRIKPKSA-N monocrotophos Chemical compound CNC(=O)\C=C(/C)OP(=O)(OC)OC KRTSDMXIXPKRQR-AATRIKPKSA-N 0.000 description 1
- AAODITQHEOZMMF-UHFFFAOYSA-N morpholine tridecane Chemical compound N1CCOCC1.CCCCCCCCCCCCC AAODITQHEOZMMF-UHFFFAOYSA-N 0.000 description 1
- BLCKKNLGFULNRC-UHFFFAOYSA-L n,n-dimethylcarbamodithioate;nickel(2+) Chemical compound [Ni+2].CN(C)C([S-])=S.CN(C)C([S-])=S BLCKKNLGFULNRC-UHFFFAOYSA-L 0.000 description 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-M naphthalene-1-sulfonate Chemical compound C1=CC=C2C(S(=O)(=O)[O-])=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-M 0.000 description 1
- 229920001206 natural gum Polymers 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229940055577 oleyl alcohol Drugs 0.000 description 1
- XMLQWXUVTXCDDL-UHFFFAOYSA-N oleyl alcohol Natural products CCCCCCC=CCCCCCCCCCCO XMLQWXUVTXCDDL-UHFFFAOYSA-N 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- UWVQIROCRJWDKL-UHFFFAOYSA-N oxadixyl Chemical compound CC=1C=CC=C(C)C=1N(C(=O)COC)N1CCOC1=O UWVQIROCRJWDKL-UHFFFAOYSA-N 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 235000020232 peanut Nutrition 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- OGYFATSSENRIKG-UHFFFAOYSA-N pencycuron Chemical compound C1=CC(Cl)=CC=C1CN(C(=O)NC=1C=CC=CC=1)C1CCCC1 OGYFATSSENRIKG-UHFFFAOYSA-N 0.000 description 1
- LKPLKUMXSAEKID-UHFFFAOYSA-N pentachloronitrobenzene Chemical group [O-][N+](=O)C1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl LKPLKUMXSAEKID-UHFFFAOYSA-N 0.000 description 1
- XAMUDJHXFNRLCY-UHFFFAOYSA-N phenthoate Chemical compound CCOC(=O)C(SP(=S)(OC)OC)C1=CC=CC=C1 XAMUDJHXFNRLCY-UHFFFAOYSA-N 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- YEBIHIICWDDQOL-YBHNRIQQSA-N polyoxin Polymers O[C@@H]1[C@H](O)[C@@H](C(C=O)N)O[C@H]1N1C(=O)NC(=O)C(C(O)=O)=C1 YEBIHIICWDDQOL-YBHNRIQQSA-N 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 238000004382 potting Methods 0.000 description 1
- 238000003672 processing method Methods 0.000 description 1
- PWYIUEFFPNVCMW-UHFFFAOYSA-N propaphos Chemical compound CCCOP(=O)(OCCC)OC1=CC=C(SC)C=C1 PWYIUEFFPNVCMW-UHFFFAOYSA-N 0.000 description 1
- KKMLIVYBGSAJPM-UHFFFAOYSA-L propineb Chemical compound [Zn+2].[S-]C(=S)NC(C)CNC([S-])=S KKMLIVYBGSAJPM-UHFFFAOYSA-L 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- JOOMJVFZQRQWKR-UHFFFAOYSA-N pyrazophos Chemical compound N1=C(C)C(C(=O)OCC)=CN2N=C(OP(=S)(OCC)OCC)C=C21 JOOMJVFZQRQWKR-UHFFFAOYSA-N 0.000 description 1
- 150000003856 quaternary ammonium compounds Chemical group 0.000 description 1
- FBQQHUGEACOBDN-UHFFFAOYSA-N quinomethionate Chemical compound N1=C2SC(=O)SC2=NC2=CC(C)=CC=C21 FBQQHUGEACOBDN-UHFFFAOYSA-N 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 210000000582 semen Anatomy 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
- APSBXTVYXVQYAB-UHFFFAOYSA-M sodium docusate Chemical compound [Na+].CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC APSBXTVYXVQYAB-UHFFFAOYSA-M 0.000 description 1
- 229940080264 sodium dodecylbenzenesulfonate Drugs 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 238000000935 solvent evaporation Methods 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 238000009331 sowing Methods 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- QTENRWWVYAAPBI-YCRXJPFRSA-N streptomycin sulfate Chemical compound OS(O)(=O)=O.OS(O)(=O)=O.OS(O)(=O)=O.CN[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@@H]1[C@](C=O)(O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](N=C(N)N)[C@H](O)[C@@H](N=C(N)N)[C@H](O)[C@H]1O.CN[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@@H]1[C@](C=O)(O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](N=C(N)N)[C@H](O)[C@@H](N=C(N)N)[C@H](O)[C@H]1O QTENRWWVYAAPBI-YCRXJPFRSA-N 0.000 description 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
- ROZUQUDEWZIBHV-UHFFFAOYSA-N tecloftalam Chemical compound OC(=O)C1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1C(=O)NC1=CC=CC(Cl)=C1Cl ROZUQUDEWZIBHV-UHFFFAOYSA-N 0.000 description 1
- 150000003512 tertiary amines Chemical group 0.000 description 1
- BSYVTEYKTMYBMK-UHFFFAOYSA-N tetrahydrofurfuryl alcohol Chemical compound OCC1CCCO1 BSYVTEYKTMYBMK-UHFFFAOYSA-N 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- 239000004308 thiabendazole Substances 0.000 description 1
- 235000010296 thiabendazole Nutrition 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
- 229960004546 thiabendazole Drugs 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- QGHREAKMXXNCOA-UHFFFAOYSA-N thiophanate-methyl Chemical group COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC QGHREAKMXXNCOA-UHFFFAOYSA-N 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 229960002447 thiram Drugs 0.000 description 1
- KUAZQDVKQLNFPE-UHFFFAOYSA-N thiram Chemical compound CN(C)C(=S)SSC(=S)N(C)C KUAZQDVKQLNFPE-UHFFFAOYSA-N 0.000 description 1
- OBZIQQJJIKNWNO-UHFFFAOYSA-N tolclofos-methyl Chemical compound COP(=S)(OC)OC1=C(Cl)C=C(C)C=C1Cl OBZIQQJJIKNWNO-UHFFFAOYSA-N 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- BAZVSMNPJJMILC-UHFFFAOYSA-N triadimenol Chemical compound C1=NC=NN1C(C(O)C(C)(C)C)OC1=CC=C(Cl)C=C1 BAZVSMNPJJMILC-UHFFFAOYSA-N 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- RROQIUMZODEXOR-UHFFFAOYSA-N triforine Chemical compound O=CNC(C(Cl)(Cl)Cl)N1CCN(C(NC=O)C(Cl)(Cl)Cl)CC1 RROQIUMZODEXOR-UHFFFAOYSA-N 0.000 description 1
- 239000005051 trimethylchlorosilane Substances 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
- 238000005406 washing Methods 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- CHNQZRKUZPNOOH-UHFFFAOYSA-J zinc;manganese(2+);n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[Zn+2].[S-]C(=S)NCCNC([S-])=S.[S-]C(=S)NCCNC([S-])=S CHNQZRKUZPNOOH-UHFFFAOYSA-J 0.000 description 1
- AMHNZOICSMBGDH-UHFFFAOYSA-L zineb Chemical compound [Zn+2].[S-]C(=S)NCCNC([S-])=S AMHNZOICSMBGDH-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/02—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements
- C07D295/027—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements containing only one hetero ring
- C07D295/03—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements containing only one hetero ring with the ring nitrogen atoms directly attached to acyclic carbon atoms
-
- 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
- A01N33/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds
- A01N33/02—Amines; Quaternary ammonium compounds
- A01N33/04—Nitrogen directly attached to aliphatic or cycloaliphatic carbon atoms
-
- 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
- A01N33/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds
- A01N33/02—Amines; Quaternary ammonium compounds
- A01N33/08—Amines; Quaternary ammonium compounds containing oxygen or sulfur
- A01N33/10—Amines; Quaternary ammonium compounds containing oxygen or sulfur having at least one oxygen or sulfur atom directly attached to an aromatic 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
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-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
- A01N43/60—1,4-Diazines; Hydrogenated 1,4-diazines
-
- 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
- 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
- A01N55/00—Biocides, pest repellants or attractants, or plant growth regulators, containing organic compounds containing elements other than carbon, hydrogen, halogen, oxygen, nitrogen and sulfur
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/10—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with radicals containing only carbon and hydrogen atoms attached to ring carbon atoms
- C07D211/14—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with radicals containing only carbon and hydrogen atoms attached to ring carbon atoms with hydrocarbon or substituted hydrocarbon radicals attached to the ring nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D211/20—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms
- C07D211/22—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms by oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/06—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by halogen atoms or nitro radicals
- C07D295/073—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by halogen atoms or nitro radicals with the ring nitrogen atoms and the substituents separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
- C07D295/096—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
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Abstract
具有杀真菌作用的式(Ⅰ)化合物和它的立体异构体以及它们的酸加成盐,式中R1-R6各自代表,氢原子,含C1-4的烷基或卤原子,R7、R8各自代表含C1-4的烷基或共同形成可以含有另一杂原子的环,X和Y各自代表氢、卤原子、烷基、环烷基、链烯基、炔基、芳基、芳烷基、烷氧基或芳氧基或为式(Ⅱ)基团,式中R9-R11可以是烷基、链烯基、炔基、环烷基或芳基。
Description
本发明是关于含有叔胺基团的环丙胺杀真菌剂、制备该类药物的方法,含有该类药物的杀真菌组合物以及用该类药物对付真菌,特别是对付植物真菌病害的方法。
本发明提供具有通式(Ⅰ)的化合物,
它们的立体异构体以及酸加成盐,其中R1、R2、R3、R4、R5和R6分别代表氢原子、含1~4个碳原子的烷基或者卤原子,R7和R8分别代表氢原子或者含1~4个碳原子的烷基,或者共同形成含有另外一个杂原子的环,x和y分别代表氢原子或卤原子,或烷基,环烷基,链烯基,炔基、芳基、芳烷基、烷氧基、芳氧基,或代表基团
其中R9、R10、R11可以是烷基、链烯基、炔基、环烷基或芳基。
这些化合物具有杀真菌的活性。
本发明的化合物一般以几何异构体混合物的形式获得。但是,这些或其它光学异构体的混合物可以用本发明的工艺方法分离成单个异构体,这些异构体也是本发明内容的一部分。
当R7和R8和相邻氮原子一起代表杂环,例如哌啶、吗啉、硫代吗啉、吡咯烷或者哌嗪环时,上述任一环可能带有取代基,例如一个或几个含1~4个碳原子的烷基、苯基或羟烷基。
这些烷基或烷氧基,特别是对于x和y取代基、自R1到R8以及R9到R11取代基而言,烷基为含有1~6个碳原子(对x和y而言)或1~4个碳原子(对自R1到R11而言)的直链或支链烷基,实例是甲基,乙基,丙基(包括正丙基或异丙基)和丁基(包括正丁基、另丁基、异丁基或叔丁基)和相应的烷氧基。对于x和y而言,环烷基可以是环丙基、环丁基、环戊基或环己基。
自R1到R6以及x和y代表的卤原子可以是氟、氯或者溴。
x和y代表的链烯基和炔基可以含有2~6个碳原子,R9、R10和R11代表的链烯基或烃基可以含有2~4个碳原子。
当x和y代表芳基,芳烷基,芳氧基或芳烷氧基时,实际例子是苯基,苄基、苯氧基和苄氧基。这些环可以带有取代基,如卤素(氟氯、或溴),1~6个碳原子的烷基(如甲基、乙基、正丙基、异丙基),丁基(如正丁基、另丁基、异丁基或叔丁基),1~6个碳原子的烷氧基(如甲氧基、乙氧基、丙氧基和丁氧基),卤代的1~6个碳原子的烷氧基(如三氟甲氧基),卤代的1~6个碳原子的烷基(如三氟甲基),硝基,苯基和苯氧基。苯环可以是未取代的,或者带有上面列举的环状取代基。取代基x和y可以位于苯环的2位,3位或4位,并且最好是4位。
与上述化合物形成酸加成盐的酸可以是无机酸或者有机酸,例如盐酸、硝酸、硫酸、乙酸、对甲苯磺酸或草酸。
另一方面,本发明提供具有通式(Ⅰ)的化合物,
它们的立体异构体和酸加成盐,其中R1、R2、R3、R4、R5和R6可以相同也可以不相同,它们代表氢原子、含有1~4个碳原子的烷基、卤原子;R7和R8可以相同也可以不相同,它们代表氢原子、或含有1~4个碳原子的烷基,或二者共同形成一个环,该环可以含有氧、氮或硫作为杂原子,并且可以被选择性地取代;x和y可以相同也可以不相同,它们代表氢原子或卤原子、含有1~6个碳原子的烷基、含有3~6个碳原子的环烷基、分别含有2~6个碳原子的链烯基或炔基、苯基、苄基、含有1~6个碳原子的烷氧基、苯氧基、苄氧基或者
基团,其中R9、R10和R11可以相同也可以不相同,它们代表由直到4个碳原子组成的烷基、分别含有2~4个碳原子链烯基或炔基、含3~6个碳原子的环烷基或者苯基。
此外,本发明也提供了具有通式(Ⅰ)的化合物,
它们的立体异构体和酸加成盐,其中R1和R2是氢、卤素或1~4个碳原子的烷基;R3和R4是氢;R5和R6是氢原子或1~4个碳原子的烷基;R7和R8是1~4个碳原子的烷基,或者与相邻氮原子一起代表哌啶、吗啉、硫代吗啉或哌嗪环,这些环可以被1~4个碳原子的烷基、苯基或羟甲基取代;x和y是氢、卤素、1~4个碳原子的烷基,1~4个碳原子的烷氧基、苯基、苯氧基、苄基、苄氧基、或者
基团,其中R9、R10和R11是1~4个碳原子的烷基。
而且,本发明还提供了具有通式(Ⅰ)的化合物,
它们的立体异构体和酸加成盐,其中R1和R2是氢、甲基或者氯;R3和R4是氢;R5和R6是氢或甲基;R7和R8是哌啶、3,5-二甲基哌啶、吗啉、2,6-二甲基吗啉、二乙氨基、4-苯基哌啶、3-羟甲基哌啶、硫代吗啉、哌嗪,或4-苯基哌嗪;x和y是苯环3位和4位上的取代基,其中一个取代基是氢原子或1~4个碳原子的烷基,另一个取代基是氢原子、1~4个碳原子的烷基1~4个碳原子的烷氧基、氯、溴、苯基、苯氧基、苄基、苄氧基、或1~4个碳原子的三烷基硅。
本发明还提供下面表Ⅰ中具体列出的化合物,实例1到实例6的化合物,以及它们的立体异构体和酸加成盐。
本发明特别提供具有下列结构的化合物:
本发明提供的化合物的例子见表Ⅰ,这些化合物均符合通式(Ⅰ)其中部分化合物结构的1H核磁共振谱的化学位移值已被列出以供鉴别各种化合物。
具有通式(Ⅰ)的化合物,其中R1~R6均为氢,
是顺式2,6-二甲基吗啉,并且Ar/CH2成反式,这些化合物的13C核磁共振谱的化学位移值列于表Ⅱ,关于Ar/CH2的关系,请参看通式(Ⅰ),芳基
的位置在环丙烷环的左边,基团
(因为此处R3和R4均等于氢,所以这个基团就是-CH2-)的位置在环丙烷环的右边,也就是说,二者互为反式。
通式(Ⅰ)化合物的制法
是将具有通式(Ⅱ)的化合物
(式中R1、R2、R3、R4、R5、R6、x和y的定义均同上所述,Z是离去基团,例如氯、溴、甲磺酰氧基或对甲苯磺酰氧基),用具有通式(Ⅲ)的胺处理,
式中R7和R8的定义同上所述,反应可以用乙醇或四氢呋喃作为溶剂,或者最好不使用溶剂,反应温度是20~100℃。化合物(Ⅱ)的制法是将具有通式(Ⅳ)的醇,
(式中R1、R2、R3、R4、R5、R6、x和y的定义均同上所述),与常用卤化剂(如当Z=Cl时,用三氯化磷、五氯化磷或三氯氧化磷,当Z=Br时,用三溴化磷、五溴化磷或三溴氧化磷)反应,或者当Z=oSO2CH3(甲磺酰氧基)时,在吡啶(或三乙胺)存在下用甲磺酰氯处理,或者当Z=oSO2 (甲苯磺酰氧基)时,在吡啶(或三乙胺)存在下用甲苯磺酰氯处理。
上述醇(Ⅳ),式中R3=R4=H,其制法是将具有通式(Ⅴ)的酯用还原剂处理,
式中R1、R2、R5、R6、x和y的定义同上所述,R是烷基,还原剂通常是氢化铝锂,合适的溶剂是乙醚或四氢呋喃。
上述醇(Ⅳ),当R3=R4=烷基时,其制法是将上述酯(Ⅴ)在合适的溶剂(如乙醚或四氢呋喃)中用过量的烷基卤化镁或用过量的烷基锂处理。
上述酯(Ⅴ)的制法是将具有通式(Ⅵ)的肉桂酸酯
式中R、R5、R6、x和y的定义同上所述,与具有通式(Ⅶ)的膦烷反应,
式中R1和R2的定义同前所述,反应在适当的溶剂(如四氢呋喃)中进行。
通式(Ⅴ)的酯(其中R5=H)的另一种制法是将重氮基乙酸乙酯加到具有通式(Ⅷ)的烯烃上,
式中R1、R2、R6、x和y的定义同前所述,合适的反应溶剂是氯仿或二氯甲烷,反应中用一适当的催化剂,例如无水硫酸铜。
通式(Ⅰ)中R3=R4=H的化合物,也可以用还原剂(通常是氢化铝锂)与具有通式(Ⅸ)的酰胺反应制得,合适的反应溶剂是乙醚或四氢呋喃,
式中R1、R2、R5、R6、R7、R8、x和y的定义同上所述。
具有通式(Ⅸ)的酰胺的制法是将具有通式(Ⅹ)的酰氯
式中R1、R2、R5、R6、x和y的定义同上所述,与具有通式(Ⅲ)的胺反应,合适的反应溶剂是乙醚或四氢呋喃。
具有通式(Ⅹ)的酰氯的制法是将具有通式(Ⅺ)的羧酸与常用氯化剂如氯化亚砜或草酰氯反应,合适的反应溶剂是己烷或二氯甲烷,
式中R1、R2、R5、R6、x和y的定义同上所述。
具有通式(Ⅺ)的羧酸的制法是将酯(Ⅴ)按常法进行水解,水解反应在氢氧化钠或氢氧化钾的甲醇/水溶液和室温下进行。
通常,通式(Ⅳ)的化合物(式中R1=R2=卤素)的制法是将取代的烯丙醇(Ⅻ)与二卤碳烯进行加成反应,合适的反应溶剂是氯仿或二氯甲烷,
式中R3、R4、R5、R6、x和y的定义同上所述。
化合物(Ⅵ)、(Ⅷ),和(Ⅻ)可以用文献提出的标准方法制备。
具有通式(Ⅰ)的化合物的盐可以通过已知方法从这些化合物制得。
上述化合物、盐和金属络合物都是有效杀真菌药,特别是对付小麦的隐匿柄锈菌(小麦叶诱病菌),条形柄锈菌或者其它锈菌,大麦上的大麦柄锈菌、条形柄锈菌或者其它锈菌,以及对付其它寄主(如咖啡、苹果、蔬菜和观赏植物)上的锈菌,对付大麦和小麦上的禾白粉菌(粉状霉菌)以及其它各种寄主(例如……)上的粉状霉菌,南瓜属植物(如黄瓜)上的单丝壳,苹果上的苹果白粉病菌,葡萄上的葡萄钩丝壳,蠕孢菌,如大麦网斑病菌、喙孢菌,谷物上的假尾孢蔓毛壳,花生上的落花生尾孢,或者甜菜、香蕉、大豆等作物上的尾孢,土豆、草莓、葡萄等寄主上的葡萄孢(灰色霉菌),苹果上的苹果黑星菌(疱痂病)。
某些化合物在体外试验中也已经显示出具有广泛的抗真菌的活性。它们对各种收获后水果的病害有效,例如柑桔的指状青霉和意大利青霉菌,香蕉土的香蕉盘长孢菌。另外,某些化合物作为种子拌药能有效对付镰孢菌、针孢菌、腥黑粉菌(如黑穗病一小麦的一种由种子传播的疾病)、黑粉菌、蠕孢菌、谷物上的假尾孢蔓毛壳、棉花上的立枯丝核菌、水稻上的笹木伏革菌。
这些化合物能够在植物组织内向顶移动。而且,它们还有足够大的挥发性,使其蒸气状态能够抗植物上的真菌。
这些化合物除了农业上的用途外,也可以用作工业上的杀真菌剂,例如防止真菌损坏木材,生皮,皮革,特别是油漆膜。
这些化合物既可以单独用于真菌,也可以比较方便地配成组合物供抗真菌,因此本发明提供了抗真菌的组合物,它含有由前述定义的通式(Ⅰ)表示的化合物或它们的盐、金属络合物、醚或酯以及经选择的载体或稀释剂。
本发明还提供了对付真菌的方法,该方法为将前面定义过的化合物或它们的盐、金属络合物、醚或酯应用于植物、植物的种子、或者用于植物或种子所在的场所。
这些化合物、盐、金属络合物、醚和酯可以若干方式使用。例如它们可以配方使用或单独使用,可直接用于植物枝叶,可用于灌木和树木,用于种子或用于正在生长或将要生长的灌木或树木的中间物。它们可以喷雾、喷粉使用,可以用霜剂、糊剂配方,也可以用蒸气态或者应用缓释颗粒。可以用于作物、灌木、树木的任何一部分,例如叶、茎、枝或根,或根部周围的土壤,或播种前的种子;或用于一般土壤,或稻田水,或水裁培养殖系统。本发明的化合物还可以被注射进植物或树木内,也可以用电动喷雾技术喷雾洒在植物上。
本文中所用的术语“植物”包括籽苗、灌木和树木。另外,本发明的杀真菌的方法包括予防,保护,予防处理和根治处理。
这些化合物最好以组合物形式用于农业或园林目的。在任何情况下应用的组合物类型均取决于要达到的特定的目的。
组合物可以粉末或者颗粒形式使用,组合物含有有效成分和固体稀释剂或载体,例如可用填料如高岭土、膨润土、硅藻土、白云石、碳酸钙、滑石粉、镁石粉、福路氏土(Fuller′searth)、石膏、夏玉脱氏土(Hewitt′s earth)、硅藻土和中国粘土。可以预制成不需进一步处理即可适用于土壤使用的颗粒。这些颗粒的制法是使有效成分浸渍填料颗粒,或用有效成分和粉末状填料的混合物制成颗粒。例如拌和种子的组合物,可以含有一种辅助剂(例如矿物油),帮助组合物粘在种子上。另外为了拌和种子,有效成分也可以用有机溶剂(例如N-甲基吡咯烷酮或二甲基甲酰胺)来调配。
组合物也可以是易分散的粉末、颗粒或细粒,这些形式均含有湿润剂,以便促进含有填料和悬浮剂的粉末或颗粒在液体中分散。
水分散剂或乳剂的制法是将一种或几种有效成分溶于选择性地加有湿润剂,分散剂或乳化剂的有机溶剂之中,然后将该有机混合物加到水中(水中也可以含有湿润剂、分散剂或乳化剂)。适宜的有机溶剂是二氯乙烷、异丙醇、丙二醇、双丙酮醇、甲苯、煤油、甲基萘、二甲苯、三氯乙烯、糠醇、四氢糠醇、乙二醇醚类(如2-乙氧基乙醇、2-丁氧基乙醇)。
以喷雾使用的组合物,可以是气溶胶的形式,药物在压力下放入容器内,同时加有推进剂,例如一氟三氯甲烷、二氯二氟甲烷。
这些化合物可以在干燥状态下与烟火混合物混合,形成适合在封闭空间产生含有这些化合物的烟雾组合物。
另外,这些化合物还可以微胶囊剂形式使用。它们也可以配成生物降解的高分子组合物,以便达到慢慢地有控制地释放有效物质。
通过包含合适的附加物,例如改进分布过程的附加物、改进粘附能力的附加物、改进处理表面,以改进抗雨能力,为了多种用途,最好采用不同的组合物。
这些化合物可以与肥料(例如含氮、含钾、含磷的肥料)混合使用。只要将肥料颗粒加进,例如包上这种化合物,就成了较好的组合物。这些颗粒适合于最多含25%按重量计的化合物。因此本发明也提供一种含有通式(Ⅰ)的化合物,或它的盐或金属络合物与肥料的组合物。
这种组合物也可以是液体制剂形式,用于浸渍和喷雾,它们通常是含有有效成分的水分散剂或乳剂,同时含有一种或几种表面活性剂,例如湿润剂、分散剂、乳化剂、或悬浮剂;或者是一种适合于电动喷雾技术的喷雾剂配方。上述表面活性剂可以是阳离子型、阴离子型、或非离子型的。适宜的阳离子型表面活性剂是季铵类化合物,例如十六烷基三甲基溴化铵。
适宜的阴离子型表面活性剂是肥皂、脂肪醇单酯硫酸盐(例如十二烷基硫酸钠),芳香化合物磺酸盐(例如十二烷基苯磺酸钠,木素磺酸钠盐、钙盐或铵盐,丁基萘磺酸盐、二异丙基和三异丙基萘磺酸钠的混合物)。
适宜的非离子型表面活性剂是环氧乙烷与脂肪醇(如油醇、鲸蜡醇)的缩合产物,或与烷基苯酚(如辛基-或壬基-酚或辛基甲酚)的缩合产物。另一些非离子型表面活性剂是由长链脂肪酸和己糖醇酸酐衍生的偏酯,以及由上述偏酯与环氧乙烷或卵磷脂形成的缩合产物。适宜的悬浮剂是亲水性胶体(例如多聚乙烯吡咯烷酮和羧甲基纤维素钠),和植物胶(例如阿拉伯树胶、黄著树胶)。
以水分散剂或乳剂供用的组合物,通常形式是含有高比例有效成分的浓溶液,该浓溶液使用前用水稀释。它通常应该经得起长久贮存并且在长久贮存后能用水稀释,以便形成水制剂,这种水制剂在一段时间内是均匀的,以便能够用于人工喷雾或电动喷雾。这种浓溶液中含有效成分的重量可以达到95%,较为适宜的是在10~85%之间,例如25~60%。该浓溶液可适当的含有有机酸(例如烷基芳基磺酸或芳基磺酸,如二甲苯磺酸或十二烷基苯磺酸),因为这类酸的存在能增加浓溶液中有效成分在极性溶剂中的溶解度。该浓溶液也可适当地含有高比例的表面活性剂,以便得到在水中足够稳定的乳剂。在稀释成水制剂后,这些制剂所含有效成分的量可以按提出的目的改变,可以使用含0.0005%或0.01%到10%有效成分(按重量计)的水制剂。
本发明的组合物也可以含具有其它生物活性的化合物,例如可以含具有相似或补充抗真菌作用的化合物或具有调节植物生长作用的化合物,具有除草作用或者杀虫作用的化合物。
其它具有抗真菌作用的化合物可以举例如下:能对付谷物(如小麦)穗病害(如斑枯菌、赤霉菌和蠕孢菌)的化合物,能对付种子或土壤传播的病害的化合物,能对付葡萄上的霜霉菌或苹果上的粉状霉菌和痂病等的化合物。这些杀真菌剂的混合物比单用通式(Ⅰ)化合物有更广的抗菌谱,而且另一些杀真菌剂对通式(Ⅰ)化合物杀真菌活性具有协同作用。此处所说的另外一些杀真菌剂可以列举如下:多菌灵、苯菌灵、甲基托布津、噻菌灵、麦穗宁、氯唑灵、抑菌灵、萨摩克塞米尔(Cymoxanil)、奥克塞迪克席尔(Oxadixyl)、奥富瑞斯(Ofurace)、迈泰勒克席尔(metalaxyl)、富瓦拉克席尔(furalaxyl)、本纳勒克席尔(benalaxyl)、福瑟梯尔铝(fosetyl aluminium)、双氯苯嘧醇、依伯劳迪奥勒(iprodione)、伯罗萨米迪奥勒(Procymidione)、维克洛佐林(Vinclozolin)、帕考纳佐莱(Penconazole)、玛克洛布泰利尔(myclobutanil)、R0151297、S3308、定菌磷、乙嘧醇、灭菌磷(亚胺菌磷)、环吗啉(十三烷吗啉;克啉菌)、嗪胺灵(哌嗪宁)、努阿里莫尔(nuarimol)、楚艾布蒂尔(triazbutyl)、双辛胍胺(双胍盐)、帕劳皮可纳佐莱(Propiconazole)、帕劳奇洛拉兹(procnloraz)、费卢楚艾福尔(flutriafol)、奇洛楚艾福尔(chlortriafol)即化学品,1-(1,2,4-三氮唑-1-基)-2-(2,4-二氯苯基)己-2-醇、DPXH6573(1-((双-4-氟苯基)甲基硅)甲基)-1H-1,2,4-三氮唑,三唑二甲酮、楚艾迪迈诺尔(triadimenol)、迪奇洛布拉佐尔(diclobut-razol)、费伯罗皮莫夫(fenpropimorph)、费伯罗皮迪勒(fenpropidine)、楚阿代莫夫(triademorph)、伊默泽利尔(imazalil)、一甲呋萎灵、萎锈灵、氧化萎锈灵(萎锈散)、迈思富罗克塞恩(methfuroxam)、环烷吗啉(菌完灵;吗菌灵)、BAS454、灭瘟素、春日霉素(春雷霉素,克死霉)克瘟散(稻瘟光)、异稻瘟净、四氯苯酞、噻菌烯、稻瘟灵、三唑苯噻、皮罗夸勒恩(pyroguilan)、奇罗本兹奇佐奈(chlorbenzthiazone)、甲胂酸铁铵、多氧霉素、有效霉素赖帕罗利尔(repronil)、费卢托莱尼尔(flutolanil)、彭萨库罗(pencycuron)、迪克罗迈泽勒(diclomezine)、叶枯净、二甲基二硫代氨基甲酸镍、泰奇罗夫赛莱(techloftha-lam)、比特代诺尔(bitertanol)、磺酸丁嘧啶、埃泰可纳佐尔(etaconazole)、链霉素、萨波富瑞恩(cypofuram)、比洛克赛佐尔(biloxazol)、甲基克杀螨、甲嘧醇、费纳帕尼尔(fenapanil)、特尔克洛弗斯-迈席尔(tolclofos-methyl)、皮罗克席福尔(pyroxyfur)、代森联、代森锰、代森锰锌、敌菌丹、百菌清、敌菌灵、福美双、克菌丹、灭菌丹、代森锌、甲基代森锌、硫磺粉、消螨普、乐杀螨、利桥塞尔-阿艾索帕罗皮尔(nitrothal-isopropyl)、十二烷胍、二噻农、三苯羟基锡、乙酸三苯基锡、四氯硝基苯、五氯硝基苯、氯硝胺、含铜的化合物(如氧氯化铜、波尔多液和硫酸铜)和有机汞化合物,如1-(2-氰基-2-甲氧基亚氨基-乙酰基)-3-乙基脲。
通式(Ⅰ)化合物可以与土壤、泥炭或者其它根部介质混合以便保护植物,防止种子或土壤传播的真菌病害或枝叶真菌病害。
适宜的杀虫剂有:灭定威、乐果、异吸硫磷Ⅱ、安果、甲羰西维因,异丙威、二甲威、丁苯威、呋喃丹、卡博索尔法因(Carbos-ulfan)、地亚农、倍硫磷、杀螟松、稻丰散、氯蜱硫磷、异噁唑硫磷、丙虫磷、久效磷、布伯罗费泽因(buprofezin)、埃思罗伯罗克席费因(ethroproxyfen)和环消虫菊。
调节植物生长的化合物可以控制杂草的生长和种子盖(seedhead)形成,或选择性控制不需要的植物(例如草)的生长。
能与本发明化合物一起使用的适宜的植物生长调节剂的例子有:赤霉酸类(如GA3、GA4、或GA7)、植物激素(如尿素、费纳帕尼尔(fenapanil)、奥富瑞斯(ofurace)、帕劳皮可纳佐莱(propiconazole)、埃泰可纳佐尔(etaconazole)、和费伯罗伯莫夫(fenpropernorph)。
通式(Ⅰ)化合物可以与土壤、泥炭或其它根部介质混合以便保护植物免遭种子或土壤传播的真菌病害或枝叶真菌病害。
适宜的杀虫剂是灭定威、乐果、异吸硫磷Ⅱ,和安果。
其它植物生长调节剂可以控制杂草的生长或种子盖(Seedhead)的形成,改进通式(Ⅰ)化合物的植物生长调节作用的水平和寿命,选择性控制不需要的植物(如草)的生长,或者使通式(Ⅰ)化合物较快或者较慢地发挥植物生长调节剂作用。上述其它这类药剂还包括除草剂。
能与通式(Ⅰ)化合物混合使用并显示出协同作用的适宜的植物生长调节剂的例子有赤霉酸类(如GA3、GA4或GA7)、植物激素(如吲哚乙酸,吲哚丁酸,萘氧乙酸或萘乙酸),细胞激素(如激动素,二苯基脲,苯噻氯合剂,苄基腺嘌呤或苄基氨基嘌呤),苯氧乙酸类(如2,4-D或2甲4氯),取代苯甲酸类(如三碘苯甲酸),整形素类(如氯芴素),抑芽丹,草甘磷,催熟磷,长链脂肪醇和酸,迪凯久拉(dikegulac),帕克洛布切佐尔(paclob-utrazol),费卢尔普瑞米多尔(flurprimidol),费卢奥瑞达米德(fluoridamid),迈费卢依蒂代(mefluidide),取代季铵或鏻化合物〔如离子矮壮素、氯丁苄鏻、或迈皮夸奇洛里代(mepiguatchloride)〕,乙烯利,草威安,甲基3,6-二氯茴香酸酯,二甲基琥珀酰肼,黄草灵,脱落酸,阿艾索皮瑞穆尔(isopyrimol),1-(4-氯苯基)-4,6-二甲基-2-氧代-1,2-二氢吡啶-3-羧酸,羟基苯腈〔例如布罗穆克席里尔(bromoxynil)〕,草吡唑,苯甲酰丙-乙基3,6-二氯吡啶甲酸和四氯硝基苯。最可能出现协同作用的情况是吲哚乙酸,吲哚丁酸,萘乙酸,细胞激素(如激动素,二苯基脲、苯噻氯合剂、苄基腺嘌呤或苄基氯基嘌呤),苯氧乙酸(如2,4-D或2甲4氯),取代苯甲酸(如三碘苯甲酸),整形素类(如氯芴素),抑芽丹、草甘磷,催熟磷,长链脂肪醇和酸,迪凯久拉(dikegulac),帕克洛布切佐尔(paclobutrazol),费卢尔普瑞米多尔(flurprimidol),费卢奥瑞达米德(fluoridamid),迈费卢依蒂代(mefluidide),取代季铵或鏻化合物〔如离子矮壮素、氯丁苄鏻、或迈皮夸奇洛里代(mepiguatchloride)〕,乙烯利,草威安,甲基3,6-二氯茴香酸酯,二甲基琥珀酰肼,黄草灵,脱落酸,阿艾索皮瑞穆尔(isopyrimol),1-(4-氯苯基)-4,6-二甲基-2-氧代-1,2-二氢吡啶-3-羧酸羟基苯腈〔例如布罗穆克席里尔(bromoxynil),草吡唑,苯甲酰丙-乙基3,6-二氯吡啶甲酸,帕克洛布切佐尔(paclobut-razol),费恩佩恩泰佐尔(fenpentezol),依纳伯恩非代(inabenfide),查艾佩恩塞努尔(triapenthenol)和四氯硝基苯。
下面例子详细说明本发明,给出的温度为摄氏度(℃)。
实例1
本例子说明4-〔2-(对-叔丁基苯基)-环丙基甲基〕-哌啶(表Ⅰ的第1号化合物)的制法。取重氮基乙酸乙酯(9.74克0.085摩尔)溶于二氯甲烷(200毫升)。另取对-叔丁基苯乙烯(13.51克,0.085摩尔)和无水硫酸铜(0.1克),溶于二氯甲烷(50毫升),在90℃用注射泵(Syringe pump)将上述重氮基乙酸乙酯二氯甲烷溶液滴入,历时4小时。滴加的同时蒸出二氯甲烷。加毕,减压下除去剩余的二氯甲烷,所得棕色油状物经柱层析提纯,(硅胶柱,洗脱剂为石油醚∶乙酸乙酯=4∶1),得2-(对-叔丁基苯基)-环丙烷甲酸乙酯(产率80%),为黄色液体。
取2-(对-叔丁基苯基)-环丙烷甲酸乙酯(10.23克,0.042摩尔),在室温下滴加到氢化铝锂(1.9克,0.05摩尔)和钠干燥过的乙醚组成的混悬液中。加毕,溶液在室温下再搅拌2小时。小心地滴加乙酸乙酯(25毫升)。将混合物倒入水中,用乙醚提取,(2次,每次100毫升)。用水洗涤乙醚提取液,并用无水硫酸钠干燥。蒸去溶剂,得2-(对-叔丁基苯基)-环丙基甲醇(产率90%),为无色液体。将甲基磺酰氯(5.92克,0.052摩尔)滴加到2-(对-叔丁基苯基)-环丙基甲醇(4.79克,0.023摩尔)的吡啶(50毫升)溶液中,室温搅拌10小时。将混合物倒入水中,用乙醚提取,(2次,每次50毫升)。用水洗涤乙醚提取液(4次,每次75毫升),用无水硫酸钠干燥醚液。除去溶剂,得2-(对-叔丁基苯基)-环丙基甲基氯为棕色液体,不需提纯可用于后面一步。
取2-(对-叔丁基苯基)-环丙基甲基氯(0.53克,0.0024摩尔)和哌啶(1毫升,0.01摩尔)溶于吡啶(10毫升)中。在80℃加热10小时。冷到室温后,将混合物倒入水中,用乙醚提取。用水洗涤乙醚提取液,用无水硫酸钠干燥。除去溶剂,得桔黄色油状物,油状物经柱层析提纯(硅胶柱,洗脱剂为石油醚∶乙酸乙酯=1∶1),得标题化合物,为淡黄色油状物(0.3克,顺式∶反式CH2/Ar=1∶9)。
实例2
本例说明4-〔2-(对-叔丁基苯基)-3,3-二甲基环丙基甲基〕-吗啉(表Ⅰ的第8号化合物)的制法。将正丁基锂(30毫升,0.048摩尔)在-5℃滴加到碘化异丙基三苯鏻(20.4克,0.047摩尔)与干燥四氢呋喃(50毫升)组成的混悬液中。加毕,将溶液在-5℃搅拌40分钟,然后在-5℃将对-叔丁基肉桂酸乙酯(10克,0.043摩尔)的干燥四氢呋喃(10毫升)溶液滴入。将溶液温加热到室温,室温下搅拌5小时,倒入水中,用乙醚提取。用水洗涤乙醚提取液,用无水硫酸钠干燥,蒸发,得桔黄色油状物。将油状物溶于氯仿(50毫升),加氯化亚铜(5克)搅拌,蒸去氯仿。将残留物溶于乙醚(50毫升),过滤,除去乙醚得2-(对-叔丁基苯基)-3,3-二甲基环丙烷甲酸乙酯(12.2克),为棕色油状物,不需进一步纯化即可用于下一步。
将2-(对-叔丁基苯基)-3,3-二甲基环丙烷甲酸乙酯(8.7克,0.032摩尔),在室温和搅拌下滴加氢化铝锂(1.2克,0.032摩尔)在乙醚(30毫升)的混悬液中。室温搅拌4小时。加入乙酸乙酯(15毫升)。将混合物倒入水(5)毫升)中,用乙醚提取(2次,每次50毫升)。用水洗涤乙醚提取液(4次,每次50毫升),用无水硫酸钠干燥。除去溶剂,得2-(对-叔丁基苯基)-3,3-二甲基环丙烷甲醇(7.5克),为黄色油状物。
搅拌下于10℃将甲磺酰氯(3.5毫升)滴加到2-(对-叔丁基苯基)-3,3-二甲基环丙烷甲醇(2.2克,0.04摩尔)的吡啶(35毫升)溶液中。加毕,将混合物在室温搅拌10小时,然后倒入10N盐酸(50毫升)中,用乙醚提取(2次,每次75毫升)。合并乙醚提取液,经水洗涤(4次,每次75毫升),无水硫酸钠干燥。除去溶剂,得无色油状物,用高压液相色谱提纯(硅胶,洗脱剂为己烷),得2-(对-叔丁基苯基)-3,3-二甲基环丙烷甲基氯(3.5克)。
取2-(对-叔丁基苯基)-3,3-二甲基环丙烷甲基氯(0.8克,0.003摩尔)、吗啉(0.52克,0.006摩尔)和三乙胺(0.6克,0.006摩尔)混合,在80℃搅拌10小时。将溶液冷到室温,倒入水(20毫升)中。用水洗涤乙醚提取液。除去溶剂,得标题化合物(0.91克),为无色油状物。
实例3
本例说明4-〔2-(对-叔丁基苯基)-反式-环丙基甲基〕-2,6-顺式-二甲基吗啉(表Ⅰ的第4号化合物)的制法。取2-(对-叔丁基苯基)-环丙烷甲酸乙酯(8.0克,0.0325摩尔)溶于甲醇(80毫升)。室温下将氢氧化钾(3.65克,0.065摩尔)的水(80毫升)溶液滴入。将反应溶液回流3小时,冷到室温,小心用2M盐酸中和,加入氯化钠饱和,用乙酸乙酯提取水溶液(4次,每次100毫升),用无水硫酸钠干燥。除去溶剂,得2-(对-叔丁基苯基)-环丙烷甲酸(7.8克),为白色结晶状固体,熔点55~60℃。
取2-(对-叔丁基苯基)-环丙烷甲酸(7.8克,0.036摩尔)、草酰氯(5.5克,0.043摩尔)和己烷(80毫升)混合,室温搅拌3小时,然后在60℃温热2小时。减压除去己烷和过量的草酰氯,得2-(对-叔丁基苯基)-环丙烷甲酰氯,为淡黄色液体,不需进一步提纯即可用于下一步。
将2,6-二甲基吗啉(9.2克,0.008摩尔)于10℃滴加到2-(对-叔丁基苯基)-环丙烷甲酰氯(4.96克,0.02摩尔)在钠干燥过的乙醚(40毫升)溶液中。加毕,将反应溶液在20℃搅拌3小时,然后倒入水中,用乙醚提取(2次,每次100毫升),用水洗涤乙醚提取液,用无水硫酸钠干燥。除去溶剂,得〔2-(对-叔丁基苯基)-环丙烷〕羰基2,6-二甲基吗啉(5.6克),为桔黄色油状物。
取〔2-(对-叔丁基苯基)-环丙烷〕羰基2,6-二甲基吗啉(1.35克,0.043摩尔)溶于钠干燥过的乙醚(10毫升溶液,滴加到氢化铝锂(0.2克,0.0053摩尔)和钠干燥过的乙醚(20毫升)组成的混悬液中,将此混合物在20℃搅拌3小时。反应混合物倒入水中,用乙醚提取,用水洗涤乙醚提取液,经无水硫酸钠干燥,除去溶剂,得无色油状物,该油状物用柱层析提纯,(硅胶柱,洗脱剂为乙酸乙酯/石油醚1∶1),得标题化合物(0.48克),为无色油状物。
13C核磁共振光谱,(化学位移值,PPm,四甲基硅烷为内标)
C-1 147.998 C-8 59.221
C-2 139.377 C-9 34.075
C-3 125.145 C-10 31.222
C-4 124.927 C-11 21.918
C-5 71.345 C-12 20.088
C-6 62.942 C-13 19.065
C-7 59.532 C-14 14.665
实例4
本例说明4-〔2-(对-三甲基硅苯基)-反式-环丙基甲基〕-2,6-顺式-二甲基吗啉(表Ⅰ的第133号化合物)的制法。氮气流下,将正丁基锂(0.12摩尔,73.6毫升的1.6M溶液)于-60℃~-70℃滴加到对-溴苯乙烯(21.6克,0.12摩尔)的干燥四氢呋喃(160毫升)溶液中。加毕,将反应混合物在-60℃搅拌1 1/2 小时,在-50℃将三甲基氯硅烷(12.8克,0.12摩尔)滴入,加毕在-50℃再搅拌1/2小时。在室温搅拌1小时,小心倒入水中,用乙醚提取。用水洗涤乙醚提取液(三次),经无水硫酸钠干燥,除去溶剂,得桔黄色油状物。用柱层析提纯〔硅胶柱,洗脱剂为石油醚(沸点40℃~60℃)〕,得对-三甲基硅苯乙烯(18.90克,产率91.2%),为无色液体。
在90℃,用注射泵(Syringe pump)在5 1/2 小时内将重氮基乙酸乙酯(17.6克,0.15摩尔)的无水二氯甲烷(250毫升)溶液,滴加到对-三甲基硅苯乙烯(18.13克,0.103摩尔)和无水硫酸铜(0.4克)的干燥二氯甲烷(50毫升)溶液中,滴加的同时蒸出二氯甲烷。加毕,余下的二氯甲烷经减压除去,所得棕色油状物经柱层析提纯(硅胶柱,洗脱剂为石油醚∶乙酸乙酯=9∶1),得2-(对-三甲基硅苯基)-环丙烷甲酸乙酯(13.8克,产率51%)。
将2-(对-三甲基硅苯基)-环丙烷甲酸乙酯(13.7克,0.052摩尔)溶于甲醇(125毫升)中,室温下,将氢氧化钾(5.86克,0.105摩尔)的水(125毫升)溶液滴入。然后将溶液回流5小时,冷到室温,小心地用2M盐酸中和,加氯化钠饱和,用乙酸乙酯提取水溶液(4次,每次150毫升),经无水硫酸钠干燥,除去溶剂,得2-(对-三甲基硅苯基)-环丙烷甲酸(11.6克,产率95%),为白色结晶状固体。
取2-(对-三甲基硅苯基)-环丙烷甲酸(11.6克,0.05摩尔)、草酰氯(18.9克,0.15摩尔)和己烷(90毫升)混合,室温搅拌1小时,然后在60℃温热5小时。减压除去己烷和过量的草酰氯,得2-(对-三甲基硅苯基)-环丙烷甲酰氯(12.2克,产率97.5%),为淡黄色液体,不需进一步纯化即可用于下一步。
将2,6-二甲基吗啉(22.2克,0.19摩尔)在10℃滴入2-(对-三甲基硅苯基)-环丙烷甲酰氯(12.2克,0.048摩尔)在钠干燥过的乙醚(100毫升)溶液中。加毕,将溶液在20℃搅拌3小时。将反应混合物倒入水中,用乙醚提取(2次,每次150毫升)。用水洗涤乙醚提取液,经无水硫酸钠干燥,除去溶剂,得2-(对-三甲基硅苯基)-环丙烷羰基-2,6-二甲基吗啉(16.1克)。
将2-(对-三甲基硅苯基)-环丙烷羰基-2,6-二甲基吗啉(3.94克,0.012摩尔)在钠干燥过的乙醚(25毫升)中的溶液滴加到氢化铝锂(0.68克,0.18摩尔)和钠干燥过的乙醚(15毫升)组成的混悬液中,混合物在20℃搅拌3小时。反应混合物倒入水中,用乙醚提取。用水洗涤乙醚提取液,经无水硫酸钠干燥,除去溶剂,得无色油状物。该油状物经柱层析提纯(硅胶柱,洗脱剂为乙酸乙酯∶石油醚=1∶1),得标题化合物(2.0克)。它的二个异构体(表Ⅰ的第132号和第134号化合物)也已经进一步分离出来。
实例5
本例说明4-〔2-(对-叔丁基苯基)-2-甲基-反式-环丙基甲基〕-2,6-顺式-二甲基吗啉(表Ⅰ的第15号化合物)的制备。取氢化钠(5.45克50%油混悬物,0.11摩尔),用石油醚洗涤,混悬在干燥的二甲基亚砜(90毫升)中,在60°~70℃加热搅拌2 1/2 小时。然后反应物冷到15℃,快速搅拌下,在1/2小时内分次将溴化甲基三苯鏻(40.1克,0.11摩尔)加入,加毕,将反应混合物在室温再搅拌1小时。又在1小时内将4-叔丁基苯乙酮(20.0克,0.11摩尔)滴入。形成的混合物在室温搅拌12小时,然后倒入水(250毫升)中,用乙醚提取(4次,每次150毫升),用水洗涤乙醚提取液(4次,每次100毫升),经无水硫酸钠干燥。除去溶剂,得桔黄色油状物,经柱层析提纯(硅胶柱,洗脱剂为石油醚),得α-甲基-4-叔丁基苯乙烯(17.83克,产率90%),为无色液体。
在90℃,用注射泵(Syringe pump)在5 1/2 小时内将重氮基乙酸乙酯(13.9克,0.12摩尔)的干燥二氯甲烷(200毫升)溶液滴加到α-甲基-4-叔丁基苯乙烯(17.65克,0.10摩尔)和无水硫酸铜(0.3克)的干燥二氯甲烷(50毫升)溶液中。滴加的同时蒸出二氯甲烷。加毕,残留的二氯甲烷减压除去。所得棕色油状物经柱层析纯化(硅胶柱,洗脱剂为石油醚∶乙酸乙酯=9∶1),得2-(对-t-叔丁基苯基)-2-甲基环丙烷甲酸乙酯,(19.3克,产率73.6%),为无色油状物。
取2-(对-叔丁基苯基)-2-甲基环丙烷甲酸乙酯(18.9克,0.073摩尔)溶于甲醇(165毫升)中,室温下将氢氧化钾(8.13克,0.145摩尔)的水(165毫升)溶液滴入。溶液回流4小时,冷到室温,小心地用2M盐酸中和,加氯化钠饱和,用乙醚乙酯提取水溶液,(4次,每次150毫升),经无水硫酸钠干燥。除去溶剂,得2-(对-叔丁基苯基)-2-甲基环丙烷甲酸(16.9克,产率100%),为灰白色固体。
取2-(对-叔丁基苯基)-2-甲基环丙烷甲酸(16.2克,0.07摩尔)、草酰氯(12.3克,0.1摩尔)和己烷(130毫升)混合,在室温搅拌1小时,然后在60℃温热5小时,减压除去己烷和过量的草酰氯,得2-(对-叔丁基苯基)-2-甲基环丙烷甲酰氯(17.3克,产率100%),为淡黄色液体,不需进一步纯化即可用于下一步。
将2,6-二甲基吗啉(15.6克,0.14摩尔)在10℃滴加到2-(对-叔丁基苯基)-2-甲基环丙烷甲酰氯(8.6克0.035摩尔)的钠干燥过的乙醚(65毫升)溶液中。加毕,将溶液在20℃搅拌3 1/2 小时。将反应混合物倒入水中,用乙醚提取(2次,每次150毫升),用水洗涤乙醚提取液,经无水硫酸钠干燥。除去溶剂,得2-(对-叔丁基苯基)-2-甲基-环丙烷羰基-2,6-二甲基吗啉(12.4克,产率100%)。
将2-(对-叔丁基苯基)-2-甲基-环丙烷羰基-2,6-二甲基吗啉(11.8克,0.036摩尔)溶于钠干燥过的乙醚(60毫升),滴加到氢化铝锂(1.6克,0.042摩尔)和钠干燥过的乙醚(40毫升)组成的混悬液中,混合物在室温搅拌3小时。反应混合物小心地倒入水中,用乙醚提取。用水洗涤乙醚提取液,经无水硫酸钠干燥。除去溶剂,得无色油状物,该油状物经柱层析提纯(硅胶柱,洗脱剂为乙酸乙酯/石油醚1∶1),得标题化合物(1.5克),它的二个异构体(表Ⅰ中的第16号和第17号化合物)也已进一步分离出来。
实例6
本例说明4-〔2-(对-异丙基苯基)-3-甲基-反式-环丙基甲基〕-2,6-顺式-二甲基吗啉(表Ⅰ中的第94号化合物)的制法。取氢化钠(7.2克,50%油混悬物,0.15摩尔)用石油醚洗涤后,混悬在干燥的二甲基亚砜(120毫升)中,并于60°~70℃加热搅拌2小时。然后将反应混合物冷到15℃,快速搅拌下在1/2小时内分次将溴化乙基三苯鏻(57.4克,0.15摩尔)加入。加毕,将反应混合物在室温再搅拌1小时。然后在1小时内滴加4-异丙基苯甲醛(20克,0.13摩尔)。将反应物在室温搅拌12小时,再倒入水(300毫升)中,用乙醚提取(4次,每次150毫升)。用水洗涤乙醚提取液(4次,每次100毫升),经无水硫酸钠干燥。除去溶剂,得黄色油状物,经柱层析提纯(硅胶柱,洗脱剂为石油醚∶乙酸乙酯=9∶1),得β-甲基-4-异丙基苯乙烯(19.0克,产率90%)。
取β-甲基-4-异丙基苯乙烯(18.0克,0.11摩尔)和无水硫酸铜(0.3克),溶于干燥二氯甲烷(50毫升)中,于90℃用注射泵(Syringe pump)在5小时内将重氮基乙酸乙酯(13.0克,0.11摩尔)的干燥二氯甲烷(50毫升)溶液滴入。滴加的同时蒸出二氯甲烷。加毕,余下的二氯甲烷经减压除去。所得棕色油状物经柱层析提纯(硅胶柱,洗脱剂为石油醚∶乙酸乙酯=1∶1),得2-(对-异丙基苯基)-3-甲基环丙烷甲酸乙酯(26.0克,产率96%)。
取2-(对-异丙基苯基)-3-甲基环丙烷甲酸乙酯,(24.8克,0.1摩尔),溶于甲醇(130毫升)中,室温下将氢氧化钾(13克,0.23摩尔)在水(130毫升)中的溶液滴入。溶液回流3小时,冷到室温,小心用2M盐酸中和,用氯化钠饱和,用乙酸乙酯提取水溶液,(4次,每次150毫升),经无水硫酸钠干燥。除去溶剂,得2-(对-异丙基苯基)-3-甲基环丙烷甲酸(17.0克,产率78%)。
取2-(对-异丙基苯基)-3-甲基环丙烷甲酸(15.7克,0.07摩尔)、草酰氯(10克,0.08摩尔)和己烷(120毫升)混合,在室温搅拌2小时,然后在60℃温热3小时。减压除去己烷和过量的草酰氯,得2-(对-异丙基苯基)-3-甲基-环丙烷甲酰氯(17.0克,产率100%),为淡黄色液体,不需进一步提纯即可用于下一步。
将2,6-二甲基吗啉(5.0克,0.043摩尔),在10℃滴加到2-(对-异丙基苯基)-3-甲基环丙烷甲酰氯(5.0克,0.021摩尔)在钠干燥过的乙醚(40毫升)溶液中。加毕,溶液在20℃搅拌3小时。将反应混合物倒入水中,用乙醚提取(2次每次100毫升),用水洗涤乙醚提取液,经无水硫酸钠干燥,除去溶剂,得2-(对-异丙基苯基)-3-甲基环丙烷羰基-2,6-二甲基吗啉(6.3克,产率95%),为黄色油状物。
将2-(对-异丙基苯基)-3-甲基环丙烷羰基-2,6-二甲基吗啉(5.8克,0.018摩尔)溶于钠干燥过的乙醚(30毫升)中,并将其滴加到氢化铝锂(0.8克,0.02摩尔)和钠干燥过的乙醚(20毫升)组成的混悬液中,反应混合物在室温搅拌3小时,然后小心倒入水中,用乙醚提取。用水洗涤乙醚提取液,经无水硫酸钠干燥。除去溶剂,得无色油状物,该油状物经柱层析提纯(硅胶柱,洗脱剂为乙酸乙酯/石油醚2∶3),得标题化合物(1.1克),它的三种异构体(表Ⅰ中的第92号,第93号和第95号化合物)也已进一步分离出来。
实例7
将各成分混合,搅拌直到所有成分溶解,而制成乳油。
实例1化合物 10%
二氯乙烷 40%
十二烷基苯硫酸钙 5%
“Lubrol”L 10%
“Aromasol”H 35%
实例8
一种颗粒型组合物,容易在液体如水中分散,其制法是将前3个成分一起加水研磨,然后与醋酸钠混合。将所生成的混合物干燥,经英国标准筛(44~100号筛)过筛,即得到所需要大小的颗粒。
实例2化合物 50%
“Dispersol”T 25%
“Lubrol”APN5 1.5%
醋酸钠 23.5%
实例9
将所有成分一起研磨成为容易在液体中分散的粉剂。
实例1化合物 45%
“Disptrsol”T 5%
“Lissapol”NX 0.5%
“Cellofas”B600 2%
醋酸钠 47.5%
实例10
将有效成分溶于溶剂中,然后将它喷雾在中国粘土颗粒上,再让溶剂蒸发而形成颗粒组合物。
实例2化合物 5%
中国粘土颗粒 95%
实例11
适用于拌种的组合物,制法是将下面三种成分混合而得。
实例1化合物 50%
矿物油 2%
中国粘土 48%
实例12
将有效成分与滑石粉混合制得粉剂。
实例2化合物 5%
滑石粉 95%
实例13
将下列成分用球磨机研磨,得到的细料与水形成混悬液,制得胶体制剂。
实例1化合物 40%
“Dispersol”T 10%
“Lubrol”APN5 1%
水
实例14
将下列成分混合,然后研碎,直到所有成分完全混和均匀,即得分散的粉剂。
实例2化合物 25%
“Aerosol”OT/B 2%
“Dispersol”A.C. 5%
中国粘土 28%
硅石 40%
实例15
本例说明易分散粉剂的制法。将各成分混和后,在粉碎机内磨细即得。
实例1化合物 25%
“Perminal”BX 1%
“Dispersol”T 5%
聚乙烯吡咯烷酮 10%
硅石 25%
中国粘土 34%
实例16
将下列成分混合后磨细,配成易分散的粉剂。
实例2化合物 25%
“Aerosol”OT/B 2%
“Dispersol”A 5%
中国粘土 68%
从实例4到实例13各成分用量比例均为重量比。
表Ⅰ中列出的化合物和从第3号到第33号化合物均可按实例4到实例13专门叙述的类似方法配方。
下面解释上面提到过的各种商品名表示的物质或组合物。
LUBROL L:壬基苯酚(1摩尔)与环氧乙烷(13摩尔)的缩合物。
AROMASOL H:烷基苯的溶剂混合物。
DISPERSOL T & AC:硫酸钠与甲醛一萘磺酸钠缩合物的混合物。
LUBROL APN5:壬基苯酚(1摩尔)与萘氧化物(5.5摩尔)的缩合物。
CELLOFAS B600:羧甲基纤维素钠增稠剂。
LISSAPOL NX:壬基苯酚(1摩尔)与环氧乙烷(8摩尔)的缩合物。
AEROSOL OT/B:磺基丁=酸钠=辛酯
PERMINAL BX:烷基萘磺酸钠
实例17
测定了这些化合物对各种植物枝叶真菌病害的作用,所用的技术如下。
所用植物生长在John Innes potting Compost(第1号或第2号),直径4厘米的小罐内。被测定的化合物与含水Dispersol T一起,用珠粒研磨配制,或者应用被测化合物的丙酮溶液或丙酮/乙醇溶液,并在使用前立即稀释成所需要的浓度。对于枝叶的病害,将制剂(含100PPm有效成分)喷雾到枝叶上,并用于土壤中植物的根部。喷雾时采用最大的保留值,并给根部施药,使干土壤最后有效成分的浓度相当于大约40PPm。当用于喷雾谷物时,加入最后浓度为0.05%的吐温20。
大多数测定中,在植物被接种病害菌前1到2天,将化合物用于土壤(根)和用于枝叶(经喷雾)。一个例外情况是用禾白粉菌的测定,它是在用药前24小时给植物接种病害菌。叶的致病菌作为孢子悬液被喷雾在试验植物的叶子上。接种病菌后将该植物放回适宜环境让其产生传染病,然后孵育,直到可以评价病害的程度,根据病害的环境,接种与评价之间相隔4天到14天。
控制病害程度按下列等级记录:
4=无病害
3=轻微~5%病害,对照未用药植物计算。
2=6~25%病害,对照未用药植物计算。
1=26~59%病害,对照未用药植物计算。
0=60~100%病害,对照未用药植物计算。
测定结果见表Ⅲ。
Claims (9)
1、制备具有一般式(Ⅰ)的化合物和它们的立体异构体以及酸加成盐的方法,其特征在于在该化合物中,
其中R1、R2、R3、R4、R5和R6分别代表氢原子、含有1~4个碳原子的烷基或卤原子,R7和R8分别代表氢原子、含有1~4个碳原子的烷基或共同形成可以含有另一杂原子的环;x和y各自代表氢原子、卤原子、烷基、环烷基、链烯基、炔基、芳基、芳烷基、烷氧基、芳氧基或
基团,其中R9、R10、R11为烷基、链烯基、炔基、环烷基或芳基,该方法包括在普通溶剂如乙醇或四氢呋喃中,或者最好在没有溶剂存在下于20~100℃将一般式(Ⅱ)化合物
其中R1、R2、R3、R4、R5、R6、x和y的定义同上,Z为离去基团,如氯、溴、甲磺酰氧基、甲苯磺酰氧基,
与具有一般式(Ⅲ)的胺处理,
其中R7和R8的定义同上。
2、根据权利要求1所述的制备方法,其中在式(Ⅰ)的化合物
以及它们的立体异构体和酸加成盐中,其中R1、R2、R3、R4、R5和R6可以相同或不同,它们可以是氢原子、含有1~4个碳原子的烷基或卤原子;R7和R8可以相同或不同,它们可以是氢原子含有1~4个碳原子的烷基或共同形成可含有氧、氮或硫作为另一杂原子的环,并且该环可以被选择性地取代;x和y可以相同或不同,它们可以是氢原子、卤原子、含有1~6个碳原子的烷基、含有3~6个碳原子的环烷基、各自含有2~6个碳原子的链烯基或炔基、苯基、苄基、含1~6个碳原子的烷氧基、苯氧基、苄氧基或
基团,其中R9、R10和R11可以相同或不同,它们可以是含有直到4个碳原子的烷基,各自含有2~4个碳原子的链烯基或炔基,含有3~6个碳原子的环烷基或苯基。
4、根据权利要求1所述的制备,其中在式(Ⅰ)的化合物
以及它们的立体异构体和酸加成盐,其中R1和R2为氢、甲基或氯;R3和R4为氢;R5和R6为氢或甲基;R7和R8为哌啶、3,5-二甲基哌啶、吗啉、2,6-二甲基吗啉、二乙氨基、4-苯基哌啶、3-羟甲基哌啶、硫代吗啉、哌嗪或4-苯基哌嗪;x和y为苯环3位或4位的取代基,并且其中一个取代基为氢或C1~4烷基,而另一取代基为氢、C1~4烷基、C1~4烷氧基、氯、溴、苯基、苯氧基、苄基、苄氧基或1~4个碳原子的三烷基硅。
5、权利要求1中所述的方法,其中化合物(Ⅱ)的制备方法为将具有一般式(Ⅳ)的醇
其中R1、R2、R3、R4、R5、R6、x和y的定义同上与常用的卤化剂(如当Z为氯时,用三氯化磷、五氯化磷或三氯氧化磷,当Z为溴时,用三溴化磷、五溴化磷或三溴氧化磷)处理,或当Z为甲磺酰氧基时,在吡啶(或三乙胺)中用甲磺酰氯处理,或者当Z为甲苯磺酰氧基时,在吡啶(或三乙胺)中用甲苯磺酰氯处理,如果需要,(a)其中R3和R4均为氢的醇(Ⅳ)可以通过将具有一般式(Ⅴ)的酯
其中R1、R2、R5、R6、x和y的定义同上,R为烷基,与还原剂(一般为氢化铝锂)在普通试剂如乙醚或四氢呋喃中处理制得,或者(b)R3和R4均为烷基的醇(Ⅳ)可以将上述酯(Ⅴ)与过量烷基卤化镁或过量烷基锂在普通试剂如乙醚或四氢呋喃中处理制得,酯(Ⅴ)或者可以通过使具有一般式(Ⅵ)的肉桂酸酯
其中R、R5、R6、x和y的定义同上,
与具有一般式(Ⅶ)的膦烷
其中R1和R2的定义同上,
在普通溶剂如四氢呋喃中反应制得,具有一般式(Ⅴ)的酯(其中R5为氢)的另一制法是将重氮基乙酸乙酯加到具有一般式(Ⅷ)的烯烃中制得,
式中R1、R2、R6、x和y的定义同上,
反应在普通溶剂如氯仿或二氯甲烷中进行,反应中应用适当催化剂如无水硫酸铜。
8、杀真菌剂组合物包括按权利要求1~4所述的具有一般式(Ⅰ)的化合物或它们的酸加成盐或立体异构体和选择性的载体或稀释剂。
9、杀真菌的方法,该方法包括将权利要求1~4中任何一项的化合物或它们的酸加成盐或立体异构体,或按权利要求8的组合物应用于植物、植物种子或应用于植物或种子所在的场所。
Applications Claiming Priority (10)
Application Number | Priority Date | Filing Date | Title |
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GB8501169 | 1985-01-17 | ||
GB858501169A GB8501169D0 (en) | 1985-01-17 | 1985-01-17 | Heterocyclic compounds |
GB8512400 | 1985-05-16 | ||
GB858512400A GB8512400D0 (en) | 1985-05-16 | 1985-05-16 | Tertiary amine compounds |
GB858516804A GB8516804D0 (en) | 1985-07-03 | 1985-07-03 | Tertiary amine compounds |
GB8516804 | 1985-07-04 | ||
GB8520592 | 1985-08-16 | ||
GB858520592A GB8520592D0 (en) | 1985-08-16 | 1985-08-16 | Tertiary amine compounds |
GB858529482A GB8529482D0 (en) | 1985-11-29 | 1985-11-29 | Tertiary amine compounds |
GB8529482 | 1985-11-29 |
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CN86100254A true CN86100254A (zh) | 1986-10-08 |
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CN198686100254A Pending CN86100254A (zh) | 1985-01-17 | 1986-01-16 | 制备叔胺类化合物的方法 |
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EP (1) | EP0188887B1 (zh) |
CN (1) | CN86100254A (zh) |
AU (1) | AU5138985A (zh) |
BR (1) | BR8600138A (zh) |
DE (1) | DE3582728D1 (zh) |
DK (1) | DK12586A (zh) |
GR (1) | GR860076B (zh) |
PT (1) | PT81834B (zh) |
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GB8615313D0 (en) * | 1986-06-23 | 1986-07-30 | Ici Plc | Chemical process |
GB8617377D0 (en) * | 1986-07-16 | 1986-08-20 | Ici Plc | Tertiary amine compounds |
EP0253501A3 (en) * | 1986-07-16 | 1990-04-04 | Imperial Chemical Industries Plc | N-disubstituted cycloalkylmethyl amines useful as fungicides |
GB8621790D0 (en) * | 1986-09-10 | 1986-10-15 | Ici Plc | Tertiary amine compounds |
US6284761B1 (en) * | 1999-01-08 | 2001-09-04 | Neurogen Corporation | 1-phenyl-4-(1-[2-aryl]cyclopropyl)methylpiperazines: dopamine receptor ligands |
CN1167694C (zh) * | 1999-01-08 | 2004-09-22 | 纽罗根公司 | 1-苯基-4-(1-[2-芳基]环丙基)甲基哌嗪:多巴胺受体配体 |
EP1366030A2 (en) | 2000-07-06 | 2003-12-03 | Neurogen Corporation | Melanin concentrating hormone receptor ligands |
WO2003022820A1 (en) * | 2001-09-06 | 2003-03-20 | Bristol-Myers Squibb Pharma Company. | Heteroaromatic substituted cyclopropane as corticotropin releasing hormone |
CN101160285A (zh) | 2005-03-17 | 2008-04-09 | 辉瑞大药厂 | 适用于治疗疼痛的n-(n-磺酰氨基甲基)环丙烷甲酰胺衍生物 |
US9108948B2 (en) * | 2006-06-23 | 2015-08-18 | Abbvie Inc. | Cyclopropyl amine derivatives |
MX2008016343A (es) | 2006-06-23 | 2009-01-19 | Abbott Lab | Derivados ciclopropil amina como moduladores del receptro de histamina h3. |
US9186353B2 (en) | 2009-04-27 | 2015-11-17 | Abbvie Inc. | Treatment of osteoarthritis pain |
WO2012037258A1 (en) * | 2010-09-16 | 2012-03-22 | Abbott Laboratories | Processes for preparing 1,2-substituted cyclopropyl derivatives |
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FR1349124A (fr) * | 1961-08-23 | 1964-01-17 | Smith Kline French Lab | Procédé de préparation d'amines cyclopropyliques |
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AT354187B (de) * | 1976-11-22 | 1979-12-27 | Hoffmann La Roche | Fungizides mittel |
DE2656747C2 (de) * | 1976-12-15 | 1984-07-05 | Basf Ag, 6700 Ludwigshafen | Morpholinderivate |
DE3220732A1 (de) * | 1982-06-02 | 1983-12-08 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung von 2,2-dimethyl-3-arylcyclopropancarbonsaeuren (carbonsaeureestern), neue zwischenprodukte hierfuer und verfahren zu deren herstellung |
DE3333239A1 (de) * | 1983-09-12 | 1985-03-28 | Schering AG, 1000 Berlin und 4709 Bergkamen | Arylmethylaetherderivate, schaedlingsbekaempfungsmittel enthaltend diese verbindungen sowie verfahren zu ihrer herstellung |
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1985
- 1985-12-12 DE DE8585309054T patent/DE3582728D1/de not_active Expired - Fee Related
- 1985-12-12 EP EP19850309054 patent/EP0188887B1/en not_active Expired
- 1985-12-18 AU AU51389/85A patent/AU5138985A/en not_active Abandoned
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1986
- 1986-01-10 DK DK12586A patent/DK12586A/da not_active Application Discontinuation
- 1986-01-14 GR GR860076A patent/GR860076B/el unknown
- 1986-01-14 PT PT8183486A patent/PT81834B/pt unknown
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- 1986-01-16 CN CN198686100254A patent/CN86100254A/zh active Pending
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DK12586D0 (da) | 1986-01-10 |
EP0188887B1 (en) | 1991-05-02 |
DK12586A (da) | 1986-07-18 |
EP0188887A1 (en) | 1986-07-30 |
GR860076B (en) | 1986-01-16 |
PT81834A (en) | 1986-02-01 |
AU5138985A (en) | 1986-07-24 |
PT81834B (en) | 1987-11-19 |
DE3582728D1 (de) | 1991-06-06 |
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