CN1022885C - 含有丙烯酸衍生物作为活性成分的农用组合物,其应用制备方法 - Google Patents
含有丙烯酸衍生物作为活性成分的农用组合物,其应用制备方法 Download PDFInfo
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- CN1022885C CN1022885C CN87103544A CN87103544A CN1022885C CN 1022885 C CN1022885 C CN 1022885C CN 87103544 A CN87103544 A CN 87103544A CN 87103544 A CN87103544 A CN 87103544A CN 1022885 C CN1022885 C CN 1022885C
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- alkyl
- phenyl
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 121
- 238000000034 method Methods 0.000 title claims abstract description 17
- NIXOWILDQLNWCW-UHFFFAOYSA-N Acrylic acid Chemical class OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 title description 3
- 238000002360 preparation method Methods 0.000 claims abstract description 50
- 239000000203 mixture Substances 0.000 claims description 73
- -1 alkoxy acrylic ester Chemical group 0.000 claims description 30
- 239000000376 reactant Substances 0.000 claims description 29
- 239000002904 solvent Substances 0.000 claims description 26
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 20
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 17
- 125000000217 alkyl group Chemical group 0.000 claims description 17
- 239000001257 hydrogen Substances 0.000 claims description 16
- 229910052739 hydrogen Inorganic materials 0.000 claims description 16
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 16
- 230000008635 plant growth Effects 0.000 claims description 13
- 241000238631 Hexapoda Species 0.000 claims description 12
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 12
- 239000003513 alkali Substances 0.000 claims description 11
- 230000000855 fungicidal effect Effects 0.000 claims description 11
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 11
- 125000004429 atom Chemical group 0.000 claims description 9
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 8
- 229910052736 halogen Inorganic materials 0.000 claims description 8
- 150000002367 halogens Chemical class 0.000 claims description 8
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- 241000244206 Nematoda Species 0.000 claims description 7
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 7
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 6
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 230000000749 insecticidal effect Effects 0.000 claims description 4
- 230000000843 anti-fungal effect Effects 0.000 claims description 3
- 230000001069 nematicidal effect Effects 0.000 claims description 3
- 229940121375 antifungal agent Drugs 0.000 claims description 2
- 239000003085 diluting agent Substances 0.000 claims description 2
- 125000002769 thiazolinyl group Chemical group 0.000 claims 1
- 239000000417 fungicide Substances 0.000 abstract description 6
- 239000002917 insecticide Substances 0.000 abstract description 4
- 239000005645 nematicide Substances 0.000 abstract description 4
- 239000005648 plant growth regulator Substances 0.000 abstract description 4
- 150000001252 acrylic acid derivatives Chemical class 0.000 abstract description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 92
- 239000000243 solution Substances 0.000 description 55
- 241000196324 Embryophyta Species 0.000 description 38
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 38
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical class OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 31
- 238000003756 stirring Methods 0.000 description 27
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 24
- 239000007788 liquid Substances 0.000 description 22
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 22
- 238000005160 1H NMR spectroscopy Methods 0.000 description 19
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 17
- 241000894006 Bacteria Species 0.000 description 15
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
- 238000000605 extraction Methods 0.000 description 14
- 239000003921 oil Substances 0.000 description 14
- 238000001704 evaporation Methods 0.000 description 13
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 13
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- 201000010099 disease Diseases 0.000 description 12
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 12
- 230000008020 evaporation Effects 0.000 description 12
- 238000001035 drying Methods 0.000 description 11
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 10
- 239000003153 chemical reaction reagent Substances 0.000 description 10
- 150000003839 salts Chemical class 0.000 description 10
- 239000007921 spray Substances 0.000 description 10
- 239000000126 substance Substances 0.000 description 10
- OJRUSAPKCPIVBY-KQYNXXCUSA-N C1=NC2=C(N=C(N=C2N1[C@H]3[C@@H]([C@@H]([C@H](O3)COP(=O)(CP(=O)(O)O)O)O)O)I)N Chemical compound C1=NC2=C(N=C(N=C2N1[C@H]3[C@@H]([C@@H]([C@H](O3)COP(=O)(CP(=O)(O)O)O)O)O)I)N OJRUSAPKCPIVBY-KQYNXXCUSA-N 0.000 description 9
- 229940125758 compound 15 Drugs 0.000 description 9
- 230000000694 effects Effects 0.000 description 9
- 239000004519 grease Substances 0.000 description 9
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 9
- 230000001105 regulatory effect Effects 0.000 description 9
- 238000012360 testing method Methods 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 239000012141 concentrate Substances 0.000 description 8
- 239000010410 layer Substances 0.000 description 8
- TZIHFWKZFHZASV-UHFFFAOYSA-N methyl formate Chemical compound COC=O TZIHFWKZFHZASV-UHFFFAOYSA-N 0.000 description 8
- 239000002245 particle Substances 0.000 description 8
- 229920006395 saturated elastomer Polymers 0.000 description 8
- 239000007787 solid Substances 0.000 description 8
- 125000001424 substituent group Chemical group 0.000 description 8
- 239000000725 suspension Substances 0.000 description 8
- 239000003643 water by type Substances 0.000 description 8
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 7
- 241000233866 Fungi Species 0.000 description 7
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 7
- 239000004480 active ingredient Substances 0.000 description 7
- 125000003118 aryl group Chemical group 0.000 description 7
- 239000002585 base Substances 0.000 description 7
- 239000000460 chlorine Substances 0.000 description 7
- 229910052801 chlorine Inorganic materials 0.000 description 7
- 238000004587 chromatography analysis Methods 0.000 description 7
- 239000000284 extract Substances 0.000 description 7
- 125000005843 halogen group Chemical group 0.000 description 7
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 7
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 7
- 239000012044 organic layer Substances 0.000 description 7
- 239000002689 soil Substances 0.000 description 7
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 6
- 240000007594 Oryza sativa Species 0.000 description 6
- 235000007164 Oryza sativa Nutrition 0.000 description 6
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 6
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 6
- 229910052794 bromium Inorganic materials 0.000 description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N dimethyl sulfoxide Natural products CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 235000009566 rice Nutrition 0.000 description 6
- 239000012312 sodium hydride Substances 0.000 description 6
- 229910000104 sodium hydride Inorganic materials 0.000 description 6
- 241000220225 Malus Species 0.000 description 5
- 235000011430 Malus pumila Nutrition 0.000 description 5
- 235000015103 Malus silvestris Nutrition 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 5
- 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
- 239000002253 acid Substances 0.000 description 5
- 125000004104 aryloxy group Chemical group 0.000 description 5
- 229910052799 carbon Inorganic materials 0.000 description 5
- 235000013339 cereals Nutrition 0.000 description 5
- 239000004927 clay Substances 0.000 description 5
- 239000003337 fertilizer Substances 0.000 description 5
- 239000007789 gas Substances 0.000 description 5
- 239000001301 oxygen Substances 0.000 description 5
- 229910052760 oxygen Inorganic materials 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- 229910052708 sodium Inorganic materials 0.000 description 5
- 238000009834 vaporization Methods 0.000 description 5
- 230000008016 vaporization Effects 0.000 description 5
- 238000005406 washing Methods 0.000 description 5
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 4
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 4
- 235000007340 Hordeum vulgare Nutrition 0.000 description 4
- 235000007688 Lycopersicon esculentum Nutrition 0.000 description 4
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 4
- 101000800755 Naja oxiana Alpha-elapitoxin-Nno2a Proteins 0.000 description 4
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 4
- 240000003768 Solanum lycopersicum Species 0.000 description 4
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 4
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
- 239000000440 bentonite Substances 0.000 description 4
- 229910000278 bentonite Inorganic materials 0.000 description 4
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 238000004440 column chromatography Methods 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 125000000753 cycloalkyl group Chemical group 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 229910052731 fluorine Inorganic materials 0.000 description 4
- 239000011737 fluorine Substances 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 238000012545 processing Methods 0.000 description 4
- 235000011121 sodium hydroxide Nutrition 0.000 description 4
- 239000000375 suspending agent Substances 0.000 description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
- 238000011282 treatment Methods 0.000 description 4
- 235000013311 vegetables Nutrition 0.000 description 4
- 239000000080 wetting agent Substances 0.000 description 4
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 4
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 description 3
- SHYZVEGDXDJRCL-UHFFFAOYSA-N 2-methyl-3-phenoxypyridine Chemical class CC1=NC=CC=C1OC1=CC=CC=C1 SHYZVEGDXDJRCL-UHFFFAOYSA-N 0.000 description 3
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- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
- VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 description 3
- 240000008067 Cucumis sativus Species 0.000 description 3
- 235000010799 Cucumis sativus var sativus Nutrition 0.000 description 3
- 241000371644 Curvularia ravenelii Species 0.000 description 3
- QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 description 3
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 3
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- 150000004696 coordination complex Chemical class 0.000 description 3
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- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 3
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- XPFVYQJUAUNWIW-UHFFFAOYSA-N furfuryl alcohol Chemical compound OCC1=CC=CO1 XPFVYQJUAUNWIW-UHFFFAOYSA-N 0.000 description 3
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- 150000002500 ions Chemical class 0.000 description 3
- DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 description 3
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 description 3
- MZRVEZGGRBJDDB-UHFFFAOYSA-N n-Butyllithium Substances [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 3
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- XAMUDJHXFNRLCY-UHFFFAOYSA-N phenthoate Chemical compound CCOC(=O)C(SP(=S)(OC)OC)C1=CC=CC=C1 XAMUDJHXFNRLCY-UHFFFAOYSA-N 0.000 description 3
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- 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
- VGPIBGGRCVEHQZ-UHFFFAOYSA-N 1-(biphenyl-4-yloxy)-3,3-dimethyl-1-(1,2,4-triazol-1-yl)butan-2-ol Chemical compound C1=NC=NN1C(C(O)C(C)(C)C)OC(C=C1)=CC=C1C1=CC=CC=C1 VGPIBGGRCVEHQZ-UHFFFAOYSA-N 0.000 description 2
- DYRMBQRXOMOMNW-UHFFFAOYSA-N 4-chloropyridine-3-carbaldehyde Chemical class ClC1=CC=NC=C1C=O DYRMBQRXOMOMNW-UHFFFAOYSA-N 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 2
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- 208000031888 Mycoses Diseases 0.000 description 2
- RGTREJUDISFMLR-UHFFFAOYSA-N N1=CC=NC=C1.[O] Chemical compound N1=CC=NC=C1.[O] RGTREJUDISFMLR-UHFFFAOYSA-N 0.000 description 2
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- PTCGDEVVHUXTMP-UHFFFAOYSA-N flutolanil Chemical compound CC(C)OC1=CC=CC(NC(=O)C=2C(=CC=CC=2)C(F)(F)F)=C1 PTCGDEVVHUXTMP-UHFFFAOYSA-N 0.000 description 1
- HKIOYBQGHSTUDB-UHFFFAOYSA-N folpet Chemical compound C1=CC=C2C(=O)N(SC(Cl)(Cl)Cl)C(=O)C2=C1 HKIOYBQGHSTUDB-UHFFFAOYSA-N 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 238000001640 fractional crystallisation Methods 0.000 description 1
- UYJUZNLFJAWNEZ-UHFFFAOYSA-N fuberidazole Chemical compound C1=COC(C=2NC3=CC=CC=C3N=2)=C1 UYJUZNLFJAWNEZ-UHFFFAOYSA-N 0.000 description 1
- 230000002538 fungal effect Effects 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 239000003292 glue Substances 0.000 description 1
- 229930182470 glycoside Natural products 0.000 description 1
- 150000002338 glycosides Chemical class 0.000 description 1
- 229940097068 glyphosate Drugs 0.000 description 1
- XDDAORKBJWWYJS-UHFFFAOYSA-M glyphosate(1-) Chemical compound OP(O)(=O)CNCC([O-])=O XDDAORKBJWWYJS-UHFFFAOYSA-M 0.000 description 1
- OXHDYFKENBXUEM-UHFFFAOYSA-N glyphosine Chemical compound OC(=O)CN(CP(O)(O)=O)CP(O)(O)=O OXHDYFKENBXUEM-UHFFFAOYSA-N 0.000 description 1
- 239000010440 gypsum Substances 0.000 description 1
- 229910052602 gypsum Inorganic materials 0.000 description 1
- 230000002650 habitual effect Effects 0.000 description 1
- 230000026030 halogenation Effects 0.000 description 1
- 238000005658 halogenation reaction Methods 0.000 description 1
- 238000003306 harvesting Methods 0.000 description 1
- 125000001072 heteroaryl group Chemical group 0.000 description 1
- 125000005553 heteroaryloxy group Chemical group 0.000 description 1
- 125000005368 heteroarylthio group Chemical group 0.000 description 1
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 1
- KGVPNLBXJKTABS-UHFFFAOYSA-N hymexazol Chemical compound CC1=CC(O)=NO1 KGVPNLBXJKTABS-UHFFFAOYSA-N 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- 150000002466 imines Chemical class 0.000 description 1
- RONFGUROBZGJKP-UHFFFAOYSA-N iminoctadine Chemical compound NC(N)=NCCCCCCCCNCCCCCCCCN=C(N)N RONFGUROBZGJKP-UHFFFAOYSA-N 0.000 description 1
- JTEDVYBZBROSJT-UHFFFAOYSA-N indole-3-butyric acid Chemical compound C1=CC=C2C(CCCC(=O)O)=CNC2=C1 JTEDVYBZBROSJT-UHFFFAOYSA-N 0.000 description 1
- 239000000750 industrial fungicide Substances 0.000 description 1
- 208000014674 injury Diseases 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- FCOAHACKGGIURQ-UHFFFAOYSA-N iprobenfos Chemical compound CC(C)OP(=O)(OC(C)C)SCC1=CC=CC=C1 FCOAHACKGGIURQ-UHFFFAOYSA-N 0.000 description 1
- ONUFESLQCSAYKA-UHFFFAOYSA-N iprodione Chemical compound O=C1N(C(=O)NC(C)C)CC(=O)N1C1=CC(Cl)=CC(Cl)=C1 ONUFESLQCSAYKA-UHFFFAOYSA-N 0.000 description 1
- WPOOICLZIIBUBM-UHFFFAOYSA-H iron;iron(3+);methyl-dioxido-oxo-$l^{5}-arsane Chemical compound [Fe].[Fe+3].[Fe+3].C[As]([O-])([O-])=O.C[As]([O-])([O-])=O.C[As]([O-])([O-])=O WPOOICLZIIBUBM-UHFFFAOYSA-H 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- UFHLMYOGRXOCSL-UHFFFAOYSA-N isoprothiolane Chemical compound CC(C)OC(=O)C(C(=O)OC(C)C)=C1SCCS1 UFHLMYOGRXOCSL-UHFFFAOYSA-N 0.000 description 1
- SDMSCIWHRZJSRN-UHFFFAOYSA-N isoxathion Chemical compound O1N=C(OP(=S)(OCC)OCC)C=C1C1=CC=CC=C1 SDMSCIWHRZJSRN-UHFFFAOYSA-N 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
- 150000002576 ketones Chemical class 0.000 description 1
- QANMHLXAZMSUEX-UHFFFAOYSA-N kinetin Chemical compound N=1C=NC=2N=CNC=2C=1NCC1=CC=CO1 QANMHLXAZMSUEX-UHFFFAOYSA-N 0.000 description 1
- 229960001669 kinetin Drugs 0.000 description 1
- 239000010985 leather Substances 0.000 description 1
- 239000011968 lewis acid catalyst Substances 0.000 description 1
- OVEHNNQXLPJPPL-UHFFFAOYSA-N lithium;n-propan-2-ylpropan-2-amine Chemical compound [Li].CC(C)NC(C)C OVEHNNQXLPJPPL-UHFFFAOYSA-N 0.000 description 1
- 150000004668 long chain fatty acids Chemical class 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- CSNNHWWHGAXBCP-UHFFFAOYSA-L magnesium sulphate Substances [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 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
- 238000001819 mass spectrum Methods 0.000 description 1
- BCTQJXQXJVLSIG-UHFFFAOYSA-N mepronil Chemical compound CC(C)OC1=CC=CC(NC(=O)C=2C(=CC=CC=2)C)=C1 BCTQJXQXJVLSIG-UHFFFAOYSA-N 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- CNTVWMRWECWTRT-UHFFFAOYSA-N methyl 2,5-dichloro-4-methoxybenzoate Chemical compound COC(=O)C1=CC(Cl)=C(OC)C=C1Cl CNTVWMRWECWTRT-UHFFFAOYSA-N 0.000 description 1
- LINPVWIEWJTEEJ-UHFFFAOYSA-N methyl 2-chloro-9-hydroxyfluorene-9-carboxylate Chemical compound C1=C(Cl)C=C2C(C(=O)OC)(O)C3=CC=CC=C3C2=C1 LINPVWIEWJTEEJ-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
- 229940017219 methyl propionate Drugs 0.000 description 1
- 239000003094 microcapsule Substances 0.000 description 1
- 239000011259 mixed solution Substances 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
- 230000000877 morphologic effect Effects 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
- CUYDUAXYJJPSRK-UHFFFAOYSA-N n-[4-methyl-3-(trifluoromethylsulfonylamino)phenyl]acetamide Chemical compound CC(=O)NC1=CC=C(C)C(NS(=O)(=O)C(F)(F)F)=C1 CUYDUAXYJJPSRK-UHFFFAOYSA-N 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 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
- 238000005580 one pot reaction Methods 0.000 description 1
- 125000002524 organometallic group Chemical group 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
- AMEKQAFGQBKLKX-UHFFFAOYSA-N oxycarboxin Chemical compound O=S1(=O)CCOC(C)=C1C(=O)NC1=CC=CC=C1 AMEKQAFGQBKLKX-UHFFFAOYSA-N 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 230000024241 parasitism Effects 0.000 description 1
- 235000021017 pears Nutrition 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
- 230000000361 pesticidal effect Effects 0.000 description 1
- AHWALFGBDFAJAI-UHFFFAOYSA-N phenyl carbonochloridate Chemical class ClC(=O)OC1=CC=CC=C1 AHWALFGBDFAJAI-UHFFFAOYSA-N 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical compound [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 description 1
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- YFGYUFNIOHWBOB-UHFFFAOYSA-N pirimicarb Chemical compound CN(C)C(=O)OC1=NC(N(C)C)=NC(C)=C1C YFGYUFNIOHWBOB-UHFFFAOYSA-N 0.000 description 1
- 229920001084 poly(chloroprene) Polymers 0.000 description 1
- 229920000642 polymer Polymers 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
- CHKVPAROMQMJNQ-UHFFFAOYSA-M potassium bisulfate Chemical compound [K+].OS([O-])(=O)=O CHKVPAROMQMJNQ-UHFFFAOYSA-M 0.000 description 1
- 229910000343 potassium bisulfate Inorganic materials 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 230000003449 preventive effect Effects 0.000 description 1
- WHHIPMZEDGBUCC-UHFFFAOYSA-N probenazole Chemical compound C1=CC=C2C(OCC=C)=NS(=O)(=O)C2=C1 WHHIPMZEDGBUCC-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- QXJKBPAVAHBARF-BETUJISGSA-N procymidone Chemical compound O=C([C@]1(C)C[C@@]1(C1=O)C)N1C1=CC(Cl)=CC(Cl)=C1 QXJKBPAVAHBARF-BETUJISGSA-N 0.000 description 1
- 230000000644 propagated effect Effects 0.000 description 1
- WZZLDXDUQPOXNW-UHFFFAOYSA-N propamocarb Chemical compound CCCOC(=O)NCCCN(C)C WZZLDXDUQPOXNW-UHFFFAOYSA-N 0.000 description 1
- ULWHHBHJGPPBCO-UHFFFAOYSA-N propane-1,1-diol Chemical class CCC(O)O ULWHHBHJGPPBCO-UHFFFAOYSA-N 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
- 239000003380 propellant Substances 0.000 description 1
- 238000011321 prophylaxis Methods 0.000 description 1
- STJLVHWMYQXCPB-UHFFFAOYSA-N propiconazole Chemical compound O1C(CCC)COC1(C=1C(=CC(Cl)=CC=1)Cl)CN1N=CN=C1 STJLVHWMYQXCPB-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
- 230000001681 protective effect Effects 0.000 description 1
- YRRBXJLFCBCKNW-UHFFFAOYSA-N prothiocarb Chemical compound CCSC(=O)NCCCN(C)C YRRBXJLFCBCKNW-UHFFFAOYSA-N 0.000 description 1
- 150000003217 pyrazoles Chemical class 0.000 description 1
- XRJLAOUDSILTFT-UHFFFAOYSA-N pyroquilon Chemical compound O=C1CCC2=CC=CC3=C2N1CC3 XRJLAOUDSILTFT-UHFFFAOYSA-N 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
- 239000002994 raw material Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000004062 sedimentation Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 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
- NESLWCLHZZISNB-UHFFFAOYSA-M sodium phenolate Chemical compound [Na+].[O-]C1=CC=CC=C1 NESLWCLHZZISNB-UHFFFAOYSA-M 0.000 description 1
- HIEHAIZHJZLEPQ-UHFFFAOYSA-M sodium;naphthalene-1-sulfonate Chemical compound [Na+].C1=CC=C2C(S(=O)(=O)[O-])=CC=CC2=C1 HIEHAIZHJZLEPQ-UHFFFAOYSA-M 0.000 description 1
- 229960005322 streptomycin Drugs 0.000 description 1
- 125000005420 sulfonamido group Chemical group S(=O)(=O)(N*)* 0.000 description 1
- 238000006277 sulfonation reaction Methods 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 239000004094 surface-active agent Substances 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
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-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
- 125000005031 thiocyano group Chemical group S(C#N)* 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
- OBZIQQJJIKNWNO-UHFFFAOYSA-N tolclofos-methyl Chemical group COP(=S)(OC)OC1=C(Cl)C=C(C)C=C1Cl OBZIQQJJIKNWNO-UHFFFAOYSA-N 0.000 description 1
- 150000003613 toluenes Chemical class 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
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 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
- FTVLMFQEYACZNP-UHFFFAOYSA-N trimethylsilyl trifluoromethanesulfonate Chemical compound C[Si](C)(C)OS(=O)(=O)C(F)(F)F FTVLMFQEYACZNP-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 238000009333 weeding Methods 0.000 description 1
- 239000004563 wettable powder Substances 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
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with 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
- C07D213/62—Oxygen or sulfur atoms
- C07D213/63—One oxygen atom
- C07D213/64—One oxygen atom attached in position 2 or 6
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/54—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
- C07D213/55—Acids; Esters
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
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Abstract
本发明涉及农业上具有式(I)的丙烯酸衍生物(除特别用作杀真菌剂外,还用作杀昆虫剂、杀线虫剂和植物生长调节剂),它们的制备方法,含这类衍生物的农用制剂,用这些制剂抗植物真菌感染,杀灭或控制昆虫和线虫虫害和调节植物生长的方法。其中W为R1O2C-C=CH-ZR2,A,B,D,E,W,Z,R1和R2和说明书定义相同。
Description
本发明涉及农业上有用的丙烯酸衍生物(除特别用作杀真菌剂外,还用作杀昆虫剂、杀线虫剂和植物生长调节剂),它们的制备方法,含这类衍生物的农用制剂,用这些制剂抗真菌、特别是抗植物真菌感染,杀灭或控制昆虫和线虫虫害和调节植物生长的方法。
本发明提供了一种具有通式(Ⅰ)的化合物和它的立体异构体,以及它们的金属络合物,
(Ⅰ)
式(Ⅰ)中W为R1O2C-C=CH-ZR2,R1和R2为烷基或氟烷基,R1和R2可以相同也可以不同,Z或为氧原子或为硫原子;A、B、D和E为氢或卤原子、或羟基、可带取代基的烷基、可带取代基的烷氧基、可带取代基的芳烷基、可带取代基的芳烷氧基、可带取代基的链烯基、可带取代基的炔基、可带取代基的芳基、可带取代基的芳氧基、可带取代基的芳硫基、可带取代基的杂芳氧基、可带取代基的杂芳硫基、可带取代基的酰氧基、可带取代基的氨基、可带取代基的芳偶氮基、可带取代基的酰氨基、硝基、氰基、-CO2R3、-CONR3R4、-COR3、-CR3=NR4、-N=CR3R4或者-S(O)nR3,A、B、D和E可以相同也可以不同;A、B、D和E基团中任何两个处于环上相邻的位置时,可连接形成或芳香稠环或脂肪稠环,该稠环可含一个或多个杂原子;n为0、1或2;R3和R4为氢原子或烷基、环烷基、环烷基烷基、链烯基、炔基、可带取代基的芳基或可带取代基的芳烷基,R3和R4可以相同或不同。
本发明的化合物至少含一个碳-碳双键,并有时制得的为几何异
构体的混合物形式。不过这些混合物能被分离成单个的异构体,并且本发明包含这类异构体以及它们各种比例的混合物,包括大部分由Z型异构体组成的混合物和大部分由E型异构体组成的混合物。
由取代基W上双键的不对称取代而生成的单一异构体使用惯用的述语“E”和“Z”作标志。这些述语是按照Cahn-Ingold-Prelog系统来定义的,该系统在文献中有透彻的叙述(例如见J March,“Advanced Organic Chemistry”3rd edition,Wiley-Interscience,P109及以下各页)。
通常是一种异构体的杀真菌活性比另一种异构体更强,在杀真菌活性更强的异构体中,W取代基(R1O2C-C=CH-ZR2)上的-ZR2与吡啶环处于双键的同一侧。在本发明的化合物的情形中,这就是E型异构体。这些异构体成为本发明的一种最佳实施方案。
在通式(Ⅰ)的化合物中,烷基和烷氧基中的烷基部分可以是直链或支链,而且以含1至6个碳原子为好,含1至4个碳原子则更好。这种烷基的例子有甲基、乙基、丙基(正丙基和异丙基)和丁基(正丁基、仲丁基、异丁基和叔丁基),环烷基,最好是3至6个碳原子的环烷基,包括环己基,环烷基烷基,最好是环烷基部分含3至6个碳原子和烷基部分含1至4个碳原子,包括环丙基乙基。链烯基和炔基以含2至6个碳原子为好,含2至4个碳原子则更好,可以是直链或支链。具体例子是乙烯基、烯丙基和炔丙基。芳基最好是苯基,而芳烷基最好是苄基、苯乙基,或苯基-正丙基。可带取代基的烷基包括特别是卤代烷基、羟烷基、烷氧烷基和可带取代基的芳氧烷基(特别是可带取代基的苯氧烷基)和可带取代基的杂芳氧烷基(特别是吡啶氧烷基和嘧啶氧烷基);可带取代基的链烯基包括可带取代基的苯基链烯基,特别是可带取代基的苯基乙烯基;可带取代基的芳基烷氧基包括可带取代基的苄氧基。
可能存在于可带取代基的芳基或杂芳基部分的取代基包括一个或多个下述基团:卤素(特别是氟、氯和溴)、羟基、C1-4烷基(特别
是甲基和乙基);C1-4烷氧基(特别是甲氧基)、C1-4卤代烷基(特别是三氟甲基)、C1-4卤代烷氧基(特别是三氟甲氧基)、C1-4烷硫基(特别是甲硫基)、C1-4烷氧基-(C1-4)烷基、C3-6环烷基、C3-6环烷基-(C1-4)烷基、芳基(特别是苯基)、芳氧基(特别是苯氧基)、芳基(C1-4)烷基(特别是苄基、苯乙基和苯基-正丙基)、芳基(C1-4)烷氧基(特别是苄氧基)、芳氧基(C1-4)烷基(特别是苯氧甲基)、酰氧基(特别是乙酰氧基和苯甲酰氧基)、氰基、氰硫基、硝基、-NR′R″、-NHCOR′、-NHCONR′R″、-CONR′R″、-COOR′、-OSO2R′、-SO2R′、-COR′、-CR′=NR″、或-N=CR′R″,其中R′和R″各自为氢、C1-4烷基、C1-4烷氧基、C1-4烷硫基、C3-6环烷基、C3-6环烷基(C1-4)烷基、苯基或苄基、该苯基或苄基可被卤素、C1-4烷基或C1-4烷氧基取代。
可带取代基的氨基、酰氨基和酰氧基包括-NR′R″、-NHCOR′和-OCOR′其中R′和R″和上面一样定义。
通式(Ⅰ)的具有特殊意义的化合物是其A、B、D和E选自下述基团的化合物:氢、卤素(特别是氟、氯和溴)、C1-4烷基(特别是甲基和乙基)、三氟甲基、C1-4烷氧基(特别是甲氧基)、三氟甲氧基、芳烷基(特别是苯基(C1-4)烷基,包括苄基、苯乙基和苯基-正丙基)、芳链烯基(特别是苯乙烯基,可以是E型或Z型异构体)、-COOR3,其中R3是C1-4烷基(特别是甲基或乙基)、C3-4链烯基(特别是烯丙基)或芳基(特别是苯基)、芳氧基(特别是苯氧基)、芳硫基(特别是苯硫基)、杂芳氧基、杂芳硫基(特别是吡啶氧基、吡啶硫基、嘧啶氧基、嘧啶硫基、吡嗪氧基、吡嗪硫基、苯并唑氧基和苯并噁唑硫基)、苄氧基、苄硫基和苯氧甲基,所有这些基团的环上可以带一个或多个取代基,如卤素(特别是氟、氯和溴)、氰基、硝基、C1-4烷基(特别是甲基)、C1-4烷氧基(特别是甲氧基)、三氟甲基和三氟甲氧基。
最好是A、B、D和E中至少有一个不为氢,而且该非氢取代基
处于吡啶环上W取代基的邻位。这样,当W处于吡啶环的2或4位时,A至E中的一个取代基处于3位,当W处于3位时(最好是如此),A至E中的一个取代基处于2位(更可取)或4位。当A、B、D和E中之任意两个取代基处于吡啶环上相邻位置时,它们可以结合成为或芳香或脂肪的稠环,比如稠合的苯环,稠环可以含1个或多个杂原子。
R1和R2中至少有一个为甲基更好,R2为甲基更可取,而两者均为甲基则尤其可取。
取代基W中的Z是氧时为最好。
因而,在列举的本发明的实施方案中,包括化合物(Ⅱ)
最好是E型异构体,其中处在丙烯酸酯基邻位的A为苯氧基(环上可被一个或多个氟、氯、溴、甲基、甲氧基、三氟甲基、三氟甲氧基、氰基或硝基取代)、苯硫基、苄基、苯乙基、苯乙烯基(或者E型或者Z型异构体)、苄氧基、苯氧甲基、苄硫基、-COOR3(其中R3为甲基、乙基、烯丙基或苯基)、吡啶氧基、吡啶硫基、嘧啶氧基、嘧啶硫基、吡嗪氧基或吡嗪硫基(环上可被氯、溴或三氟甲基取代)、或苯并噁唑氧基或苯并噁唑硫基。
本发明的化合物例示于表1中。该表中的“ph”表示苯基(即C6H5)。
表1
“ph”为苯基
*β-甲氧基丙烯酸酯基上烯质子的单峰的化学位移(ppm,TMS为内标),氘代氯仿作溶剂。
表2中选择列出了表1中的一些化合物的1HNMR数据。化学位移的单位为ppm,TMS为内标,均用氘代氯仿作溶剂进行测定。使用了下述缩写:
br=宽峰 t=三重峰
s=单峰 q=四重峰
d=双峰 m=多重峰
J=偶合常数 Hz=赫兹
具有通式(1)的本发明的化合物能通过图1、图2和图3中所列出的化学方法制备。图1、图2和图3中的R1、R2、Z、A、B、D和E都具有前面的定义,G为氢或金属原子(例如钠原子)、M为金属原子(例如锂原子)或一金属原子加上一个缔合的卤原子(例如MgI、MgBr、或MgCl)而且L为卤原子或其它优良的离去基。
通式(Ⅰ)的化合物可以作为几何异构体的混合物存在,该混合物能通过层析、蒸馏或分步结晶分离。使用下式
意欲表明一种关于丙烯酸酯双键的两个几何异构体的可分离的混合物:即
参照图1,通式(Ⅰ)的化合物(其中Z为氧而不为硫)可以通过在一合适的溶剂中用碱(例如氢化钠或醇钠)和通式为HCO2R1的甲酸酯(例如甲酸甲酯)处理通式(Ⅳ)的化合物制备(图1中的步骤(b))。如果再将通式为R2L的物质,其中L为离去基(例如卤素阴离子或R2SO4阴离子),加入到反应混合物中,便可以得到通式(Ⅰ)的化合物(图1中的步骤(a))。假如将质子酸加到反应混合物中,得到通式(Ⅲ)的化合物,其中G为氢。或者通式(Ⅲ)的化合物,其中G为金属原子(通常为一碱金属例如钠),本身可以从反应混合物中分离出来。
通式(Ⅲ)的化合物,其中G为金属原子,在适宜的溶剂中用通式为R2L的物质处理,R2L中的L具有上面的定义,能够变为通式(Ⅰ)的化合物。通式(Ⅲ)的化合物,其中G为氢,在适宜的溶剂中依次用碱(例如碳酸钾或氢化钠)和通式R2L的物质处理,能转变为通式(Ⅰ)的化合物。
或者,在适宜的温度和通常是在适当的溶剂中,使通式(Ⅻ)的缩醛或在酸性或在碱性条件下消去适当的链烷醇,能够制得通式
(Ⅰ)的化合物,其中Z为氧(图1中的步骤(c))。能够用于这种转化的试剂或试剂混合物是二异丙氨锂;硫酸氢钾(例如见于T Yamada,H Hagiwara and H Uda,J.Chem.Soc.,Chemical Communications,1980,838,和其中的参考文献);和三乙胺,常常在路易斯酸例如四氯化钛的存在下(例如见于K Nsunda and L Heresi,J.Chem.Soc.,Chemical Communications,1985,1000)。
在适宜的温度和溶剂中,在路易斯酸例如四氯化钛存在下,通式(ⅩⅢ)的烷基硅烷基烯酮缩二醇,其中R为一烷基,用通式(R2O)3CH的原甲酸三烷基酯处理,可以制备通式(Ⅻ)的缩醛类(例如见于K Saigo,M Osaki and T Mukaiyama,Chemistry let-ters,1976,769)(图1中的步骤(f))。
在适宜的溶剂中和适当的温度下,将通式(Ⅳ)的酯用碱和通式为R3SiCl或R3SiBr的卤代三烷基硅烷,例如用氯代三甲基硅烷处理,或碱和通式为R3Si-OSO2CF3的三氟甲磺酸三烷基硅烷酯处理可以制得通式(ⅩⅢ)的烷基硅烷基烯酮缩二醇(例如见于C Ainsworth,F Chen and Y Kuo,J.Organometallic Chemistry,1972,46,59)(图1中的步骤(g))。
并不总是有必要分离中间体(Ⅻ)和(ⅩⅢ);在适宜的条件下,通过依次加上面列出的适当的试剂,采用“一勺烩”的程序可以从通式(Ⅳ)的酯制备通式(Ⅰ)的化合物。
或者,在适宜的温度下,在羧酸酐(例如乙酸酐)和路易斯酸催化剂(例如氯化锌)存在下,通式(Ⅳ)的化合物用原甲酸酯HC(ZR2)3处理,可以制得通式(Ⅻ)的化合物,其中Z为氧,按照这种途径,在适当的条件下,例如提高温度或延长反应时间,可以直接制得通式(Ⅰ)的化合物(例如见于R.Huisgen,H.Seidl and J.Wulff,Chem.Ber,1969,102,915;A.Marchesini,J.Org.Chem.,1984,49,4287)(图1中的步骤(h))。
通式(Ⅳ)的化合物能通过化学文献中叙述的方法制备。例如,
在一种酸(例如氯化氢)的存在下,用一种醇R1OH处理通式(Ⅴ)的化合物,即可制得(图1中的步骤(d))。
在一种碱(例如三通B)存在下,在合适的溶剂中(例如四氢呋喃),通式(Ⅵ)的醛用单甲硫基二甲亚砜(CH3SOCH2SCH3)处理,能够制得通式(Ⅴ)的化合物(见于K.Ogura and G.Tsuchihashi,Tetrahedron Letters,1972,1383-6)(图1的步骤(e))。
通式(Ⅵ)的化合物能按照化学文献中叙述的标准方法制备。
参照图2,在一合适的溶剂(例如乙醚或四氢呋喃)中,通式(Ⅰ)的化合物能够另由用通式(Ⅷ)的膦内鎓盐处理通式(Ⅶ)的
α-酮酯制得(例如见于,EP-A-0044448 and EP-A-0178826)(图2中的步骤(a))。
通式(Ⅶ)的α-酮酯可采用化学文献中叙述的标准方法制备。例如通式(Ⅸ)的金属取代的吡啶与草酸酯(Ⅹ)在适当的溶剂(例如乙醚或四氢呋喃)中反应,能制得通式(Ⅶ)的α-酮酯(图2中的步骤(b))。(有关反应见L.M.Weinstock,R.B.Currie and A.V.Lovell,Syn.Commun.,1981,11,943及其中的参考文献)。
通式(Ⅸ)的金属取代的吡啶,能通过化学文献中叙述的标准方法制备。
另外,通式(Ⅶ)的α-酮酯可采用k.Ogura,N.Katoh,I.Yoshimura,G.Tsuchiheshi在Tetrahedron Letters,1978,375,中的方法由通式(Ⅺ)的腈制得(图2中的步骤(c))。
通式(Ⅰ)的一些化合物能通过图3表示的另一路线制备。
当A为可带取代基的苯氧甲基、苯硫甲基、烷氧甲基、烷硫甲基或羟甲基时,通式(Ⅰ)的化合物能通过通式(ⅩⅤ)的化合物与可带取代基的苯酚或硫酚在碱(例如醇钠或氢化钠)存在下在一合适的溶剂(例如二甲基甲酰胺)中反应制得,或者由通式(ⅩⅤ)的化合物与烷氧离子、烷硫离子或氢氧离子反应制得(图3中的步骤(a))。
通式(ⅩⅤ)中L为卤素的化合物能通过把通式(ⅩⅣ)的化合物在适当的溶剂中卤化,例如在四氯化碳中用N-溴代琥珀酰亚胺溴化而制得(图3中的步骤(b))。
通式(ⅩⅣ)的化合物可通过图1中表述的路线制备。
通式(Ⅰ)中A是式-CR5=CR6R7表示的可带取代基的链烯基或苯基链烯基的化合物能通过通式(ⅩⅥ)的化合物与通式(ⅩⅦ)的化合物在众所周知的Wadsworth-Emmons反应条件下(这里Y为-P(O)(OR8)2基)或众所周知的维悌希反应条件下(这里Y为-+PAr3,Ar为任意取代的苯基)反应制得。即通式(ⅩⅥ)的化合物在适当的无水溶剂(例如N,N-二甲基甲酰胺或四氢呋喃)中用适当的碱(例如氢化钠或叔丁醇钾)处理,然后用通式(ⅩⅦ)的化合物处理(图3中的步骤(c))。
通式(ⅩⅥ)的化合物可通过通式(ⅩⅤ)的化合物与亚磷酸三烷基酯,P(OR8)3或三芳基膦在合适的溶剂例如甲苯或乙醚中反应制得(图3中的步骤(d))。
贯穿于图3中的R5最好为氢,但也可以是C1-4烷基,或可带取代基的苯基;R6和R7为氢、C1-8烷基、卤代烷基、可带取代基的苯基或-CO2R3。最好是R6和R7中一个为氢,且R8为C1-4烷基,
通常是甲基或乙基。L如图1中的定义,但最好为一卤原子,例如氯或溴。
另外,本发明提供了所述的本发明化合物和所用的通式(Ⅲ)、(Ⅳ)、(Ⅴ)、(Ⅶ)和(Ⅻ)至(ⅩⅥ)的中间体化合物的制备方法。
本发明的化合物和金属络合物具有杀真菌活性,并可用于控制一种或多种病原体:
水稻上的Pyricularia oryzae;小麦上的隐匿柄锈菌、条形柄锈菌和其它锈菌;大麦上的大麦柄锈菌、条形柄锈菌和其它锈菌;以及其它宿主,例如咖啡、梨、苹果、花生、蔬菜和观赏植物上的锈菌。大麦和小麦上的禾白粉菌(粉状霉)和各种宿主上的其它粉状霉,例
如蛇麻草上的棉毛单丝壳;芦葫属(例如黄瓜)上的苍耳单丝壳;苹果上的白叉丝单囊壳和葡萄上的葡萄钩丝壳。谷类上的长蠕孢属菌、喙孢属菌、壳针孢属菌、和蔓毛壳假尾孢。花生上的落花生尾孢和裂口小尾孢以及其它宿主,例如甜菜、香蕉、黄豆和水稻上的其它尾孢属菌。蔬菜(例如黄瓜)、油菜籽、苹果、西红柿和其它宿主上的链格孢属菌。苹果上的苹果黑星菌(斑点病);葡萄上的葡萄生单轴霉;其它绒毛霉例如莴苣上的莴苣盘梗霉;黄豆、烟叶、洋葱和其它宿主上的霜霉属菌以及蛇麻草上的葎草假霜霉和葫芦类的cubensis假霜霉;土豆和西红柿上的致病疫霉以及蔬菜、草莓、鳄梨、胡椒、观赏植物、烟叶、可可和其它宿主上的其它疫霉属菌。
某些这类化合物显示了广谱的体外抗真菌活性。
某些这类化合物可能也有抗各种水果收获后疾病(例如苷桔上的指状青霉菌和意大利青霉菌以及绿色木霉和香蕉上的香蕉盘长孢)的活性。
还有一些化合物作为拌种剂具有抗各类上镰刀菌属菌、壳针孢属菌、Tilletia菌(腥黑穗病,小麦种子传播的一种疾病)、黑粉菌属菌、长蠕孢属菌和水稻上的Pyricularia Oryzae的活性。
作为本发明的另外一个方面,这里提供了杀灭真菌的方法。该方法包括将有效量的通式(Ⅰ)的杀真菌化合物施用于植物、植物的种子上或种植和播种的田地里。
一些化合物在植物组织中能向顶移动。而且,该类化合物可以是易挥发的在气相中具有足够的抗植物真菌活性。
该类化合物亦可以是有用的工业杀真菌剂(与农业用相对应),例如预防真菌侵袭木材、兽皮、皮革,特别是涂料薄膜。
本发明的化合物具有抗一系列昆虫和线虫的杀虫活性。因此本发明又提供了杀灭或控制昆虫或线虫虫害的方法,该方法包括将有效量的通式(Ⅰ)的杀虫化合物施用于昆虫或线虫或其栖身处。
用于本发明的这一用途的优选的一组化合物是,通式(Ⅰ)中
A为可带取代基的芳氧基(特别是在2位取代),B、D和E为氢,W处于环的3位上的化合物。
用于本发明的这一用途的特别优选的化合物是表1中的化合物15和化合物23。已经发现化合物15具有抗根结线虫活性,化合物23具有抗带斑黄瓜叶甲(根寄生虫幼虫)活性。
类似地,一些化合物可以显示植物生长调节活性,而且可以按适宜的比例使用以达到此目的。所以,作为本发明的又一个方面,这里提供了调节植物生长的方法,该方法包括施用有效量的通式(Ⅰ)的植物生长调节化合物于植物或种子或它们的种植或播种的地方。
虽然这类化合物能直接用于杀真菌、杀昆虫、杀线虫,或植物生长调节目的,但更合适的做法是使用载体或稀释剂配制成制剂。因而本发明提供一种杀真菌制剂,该制剂包括前面定义的通式(Ⅰ)的化合物和适用于抗真菌的载体或稀释剂。
另外,本发明提供一种杀昆虫/杀线虫制剂,该制剂包括通式(Ⅰ)的杀昆虫或杀线虫化合物并配以载体或稀释剂;本发明还提供一种植物生长调节剂,该制剂包括通式(Ⅰ)的植物生长调节化合物和载体或稀释剂。
作为杀真菌剂,该类化合物能以多种途径使用。例如能够配成制剂或不经配制直接用于植物的叶、种子或用于植物种植或生长的介质中。能以喷雾剂、粉尘剂、乳剂或糊剂使用;或以蒸汽或缓释的颗粒剂使用。能用于植物的任一部位,包括叶子、茎、枝、或根,或根周围的土壤,或播种前的种子;通常用于土壤、稻田的水或溶液培养系统。本发明的化合物亦可注入植物中或使用电动喷洒技术或其它低容量方法喷于蔬菜上。
这里使用的术语“植物”包括秧苗、灌木和乔木。另外,本发明的杀真菌方法包括预防措施、保护措施,预防性治疗和根治。
该类化合物最好以制剂的形式用于农业和园艺目的。任何实例中使用的制剂的类型将取决于设想的特殊目的。
这类制剂可以采取粉尘和颗粒的形式,其中包含活性成份(本发明的化合物)和固体稀释剂或载体例如高岭土、膨润土、白色硅藻土、白云石、碳酸钙、滑石、粉状氧化镁、漂白土、石膏、硅藻土、和陶土一类的填料。这类颗粒剂能够是预先制好的颗粒,适宜于施用于土壤而无需进一步处理。这些颗粒或者通过用活性成份浸渍填料的小球,或将活性成份和粉状填料的混合物制成小球而制得。用作拌种剂的制剂可以包括一种试剂(例如一种矿物油)帮助把制剂粘着到种子上;另外活性成份能用一有机溶剂(例如用N-甲基吡咯烷酮、丙二醇或二甲基甲酰胺)制成拌种剂。制剂亦可采用可湿性粉末或可分散于水的颗粒形式,其中包含有润湿剂或分散剂,以便促进它们在液体中分散。该粉末和颗粒亦可含填料和悬浮剂。
可乳化的浓缩物或乳剂可以通过将活性成份溶于可含润湿剂或乳化剂的有机溶剂中,然后将此混合物加到亦可含润湿剂或乳化剂的水中制得。适合的有机溶剂是芳香溶剂,比如烷基苯和烷基萘;酮,比如异佛尔酮、环己酮和甲基环己酮;氯代烃,比如氯苯和三氯乙烷;和醇类比如苄醇、糠醇、丁醇和乙二醇醚。
不溶性固体的悬浮浓缩物可以通过与分散剂球磨或珠磨而制得,且包括一悬浮剂以便阻止固体沉降。
用作喷雾剂的制剂可采用气雾剂的形式,该制剂在推进剂,例如氟代三氯甲烷或二氯二氟甲烷的存在下装在压力容器之中。
本发明的化合物能以干燥的状态与制造烟火的混合物混合,以形成适合于在限定空间产生含该类化合物的烟雾的制剂。
另外,这类化合物可以微胶囊的形式使用。它们还可以配制成可生物降解的高聚物制剂,该制剂可缓慢而有控制性地释放活性物质。
通过加入适当的添加剂,例如改进在处理表面的分布、粘着力和抗雨淋的添加剂,而得到的不同的制剂可以更好地适应各种用途。
本发明的化合物能与肥料(例如含氮、含钾或含磷的肥料)混合使用。仅仅含有化合物与颗粒肥料(例如用化合物包衣的颗粒肥料)
的混合制剂为最好。按重量计,这类颗粒宜含高达25%的化合物。因此,本发明也提供了包括肥料和通式(Ⅰ)的化合物或其盐或其金属络合物的肥料组合物。
可湿性粉剂,可乳化浓缩物和悬浮浓缩物通常含有表面活性剂,例如润湿剂、分散剂、乳化剂或悬浮剂,这些试剂可以是阳离子型、阴离子型或非离子型的试剂。
适宜的阳离子型试剂是季铵化合物,例如溴化十六烷基三甲基铵。适宜的阴离子试剂是肥皂、硫酸脂肪单酯的盐(例如硫酸十二烷基酯钠)、和磺化的芳香化合物的盐(例如十二烷基苯磺酸钠、木素磺酸钠、木素磺酸钙或木素磺酸铵、丁基萘磺酸、以及二异丙基萘磺酸钠和三异丙基萘磺酸钠的混合物)。
适宜的非离子试剂是环氧乙烷与脂肪醇例如油醇或鲸蜡醇或者与烷基苯酚例如辛基苯酚或壬基苯酚及辛基甲酚的缩合产物。其它的非离子试剂是由长链脂肪酸和己糖醇酐衍生的部分酯、上述部分酯与环氧乙烷的缩合产物、和卵磷脂类。适宜的悬浮剂是亲水性胶体(例如聚乙烯吡咯烷酮和羧甲基纤维素钠)和膨润粘土例如膨润土或硅镁土。
作为水分散液或乳化液使用的制剂通常供应的是含高比例活性成份的浓缩物,使用前用水将该浓缩物稀释。这些浓缩液最好应经得起长期储存,经过长期储存之后能用水稀释,稀释成的含水制剂能保持足够时间的均匀以便能用常规的喷洒设备使用。按重量计,浓缩物可以便当地含高达95%,最好含10-85%,例如含25-60%的活性物质。经稀释成含水制剂后,这类制剂可以根据所期望的目的含不同量的活性成分,不过按重量计算,含0.0005%或0.01%至10%活性成分的含水制剂可供使用。
本发明的制剂可以含其它生物活性物质,例如含具有相似或互补杀真菌活性的化合物或具有植物生长调节活性、除草活性或杀虫活性的化合物。
可以出现在本发明的制剂中的杀真菌化合物可以是一种能够抗谷类(例如小麦)穗病例如壳针孢属菌病、赤霉属和长蠕孢属菌病、抗种子和土壤传播的疾病和葡萄上的绒毛霉及粉状霉和苹果上的粉状霉和斑点病等等的化合物。通过包含另外的杀真菌剂,该制剂能够具有比一般仅含通式(Ⅰ)化合物的制剂有更广谱的活性。另外其它杀真菌剂对于通式(Ⅰ)的化合物的杀真菌活性能具有协同作用,可以包含在本发明的制剂中的其它杀真菌化合物的例子有多菌灵、苯菌灵、甲基托布津、涕必灵、麦穗宁、氯唑灵、抑菌灵、cymoxanil、oxadixyl、ofurace、metalaxyl、furalaxyl、4-氯-N-(1-氰基-1-乙氧甲基)-苯甲酰胺、benalaxyl、fosetyl-aluminium、双氯苯嘧醇、iprodione、胺丙威、procymidone、vinclozolin、penconazole、myclobutanil、propamocarb、diniconazole、定菌灵、乙菌定、灭菌磷、克啉菌、嗪氨灵、nuarimol、triazbutyl、双胍盐、1,1′-亚胺二(辛撐)-双胍的三乙酸盐、buthiobate、propiconazole、prochloraz、flutriafol、hexaconazole、(2RS,3RS)-2-(4-氯苯基)-3-环丙基-1-(1H-1,2,4-三唑-1-基)丁-2-醇,(RS)-1-(4-氯苯基)-4,4-二甲基-3-(1H-1,2,4-三唑-1-基甲基)戍-3-醇、flusilazole、三唑二甲酮、triadimenol、diclobutrazol、fenpropimorph、pyrifenox、fenpropidin、chlorozolinate、imazalil、甲基苯基呋喃羧酰胺,萎锈灵、氧化萎锈灵、mothruroxam、吗菌灵、BAS 454、灭瘟素、春雷霉素、克瘟散、异稻瘟净、放线菌酮、四氯苯钛、噻菌灵、富士一号、三唑苯噻、pyroquilon、chlorbenzthiazone、甲胂铁铵、多氧霉素、有效霉素、mepronil、flutolanil、pencycuron、diclomezine、叶桔净、福美镍、techlofthalam、bitertanol、磺酸丁嘧啶、etaconazole、土菌消、链霉素、eypofuram、biloxazol、灭螨猛、甲菌定、1-(2-氰基-2-甲氧基亚胺乙酰基)-3-乙基脲、
fenapanil、tolclofosmethyl、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、敌螨普、二氯萘醌、地茂散、乐杀螨、nitrothalisopropyl、多果定、二噻农、毒菌锡、薯瘟锡、四氯硝基苯、五氯硝基苯、氯硝胺、含铜化合物例如氯氧化铜、硫酸铜、和波尔多液以及有机汞化物。
通式(Ⅰ)的化合物能与泥土、泥碳或其它使根固定的介质混合,以保护植物抗种子、土壤或叶真菌疾病。
可以混合到本发明制剂中的适宜的杀虫药包括抗蚜威、乐果、甲基一0五九、安果、西维因、异丙威、二甲威、丁苯威、虫螨威、carbosulfan、二嗪农、倍硫磷、杀螟松、稻丰散、毒死蜱、异噁唑磷、丙虫磷、久效磷、buprofezin、ethroproxyfen和cycloprothrin。
植物生长调节化合物是控制杂草或籽芽形成,或选择性地控制不期望有的植物(例如野草)生长的化合物。
与本发明的化合物合用的适宜的植物生长调节化合物是九二0(例如GA3、GA4或GA7)、茁长素类(例如吲哚乙酸、吲哚丁酸、2-萘氧乙酸、或萘乙酸)、细胞分裂素(例如动力精、二苯基脲、苯并咪唑、苄基腺嘌呤、或苄氨基嘌呤)、苯氧乙酸类(例如2,4-滴或2甲4氯、苯氧乙酸)、取代苯甲酸(例如三碘代苯甲酸)、正形素(例如氯甲丹)、抑芽丹、草甘膦、草甘二膦、长链脂肪醇类和长链脂肪酸类、2,3∶4,6-氧亚异丙基-2-呋喃己酮糖酸、paclobutrazol、flurprimidol、fluoridamid、N-[2,4-二甲基-5-(三氟甲基)磺酰氨基]苯基乙酰胺、取代的季铵化合物和磷鎓化合物(例如离子矮壮素、氯丁苄鏻或mepiquatchloride)、乙烯利、草长灭、3,6-二氯茴香酸甲酯、丁酰肼、黄草灵、脱落酸、isopyrimol、1-(4-氯苯基)-4,6-二甲基-2-氧-1,2-二氢吡啶-3-羧酸、羟基苯腈类(例如溴苯腈)、离子草吡唑、新燕灵、3,6-
二氯吡啶甲酸、fenpentezol、inabenfide、triapenthenal、和四氯硝基苯。
下述实施例阐明本发明。贯穿于这些实施例中的术语“醚”代表乙醚、无水硫酸镁用于干燥溶液、包含对水敏感的中间体的反应使用无水溶剂并在氮气流下进行,除非特别指明,否则层析均使用硅胶作固定相。这里给出的红外和NMR数据均为选择性的;没有试图给出所有吸收峰。本文中使用下面的缩写,
THF=四氢呋喃 delta=化学位移
DMF=N,N-二甲基甲酰胺 CDC3=氘代氯仿
GC=气相色谱 S=单峰
MS=质谱 d=双峰
mmHg=毫米汞柱压力 t=三重峰
mg=毫克 m=多重峰
g=克 J=偶合常数
Hz=赫兹,
NMR=核磁共振。
实施例1
该实施例阐明(E)2-(2′-苯氧吡啶-3′-基)-3-甲氧基丙烯酸甲酯(表1中的化合物15)的制备。
20克2-苯氧基-3-氰基吡啶和20克阮内镍在200毫升75%的甲酸中回流搅拌1小时。将反应混合物冷却、过滤,生成的绿色溶液倾入150毫升水中。放置数小时后,2-苯氧基-3-吡啶甲醛的针状结晶析出,过滤收集结晶,水洗,空气干燥。得产物10克;熔点为88-90℃;红外峰(液体石蜡)1675cm-1;1HNMRδ值(CDCl3)7.0-7.6(m),8.15-8.4(2H,m)11.05(1H,s)。
9.95克(0.05摩尔)2-苯氧基-3-吡啶甲醛和6.2克(0.05摩尔)单甲硫基二甲基亚砜与20毫升无水四氢呋喃制成溶液,在搅拌下往里滴加7.5毫升40%的三通B的甲醇溶液。然后将反应混合物
加热回流1小时。气相色谱分析表明反应已进行完全。使反应混合物冷却,减压除去溶剂。棕色油状残留物反复用乙醚萃取,合并的乙醚萃取液蒸发,得白色结晶固体,该结晶性固体用少量乙醚洗,空气干燥,重7克;熔点为123-6℃;红外峰(液体石蜡)1565,1400,1235,1200,1060cm-1;1HNMRδ值(CDCl3)2.33(3H,s)2.8(3H,s),6.87-7.7(m),8.07(1H,s),8.1-8.6(m)。该产物6.8克溶入150毫升氯化氢的甲醇溶液(在0℃下按1∶5的比例将乙酰氯加到甲醇中而制得),在0℃搅拌1小时,然后放置过夜。反应混合物倾入水中,用碳酸氢盐溶液中和,然后用乙醚萃取。合并的乙醚萃取液干燥。过滤、滤液蒸发,得浅黄色液体。在150℃,0.1毫米汞柱压力下球管到球管(bulb-to-bulb)蒸馏,得到4.5克2-苯氧基吡啶-3-基乙酸甲酯,红外峰(液膜)1735,1580,1485,1430,1245cm-1;1HNMRδ值(CDCl3)3.71(3H,s),3.80(2H,s),6.90-8.2(m)。
汽油洗过的1.8克氢化钠(0.037摩尔,48%分散于油中)在30毫升无水二甲基甲酰胺的溶液中于搅拌和-15℃下滴加由4.5克(0.0185摩尔)2-苯氧吡啶-3-基乙酸甲酯和24克(0.4摩尔)甲酸甲酯与20毫升无水二甲基甲酰胺制成的溶液。生成黄色,拌随泡腾。30分钟后,让温度缓慢上升。室温搅拌30分钟后,反应混合物倾入250毫升水中,并用乙醚萃取两次。合并的乙醚萃取液用碳酸钾溶液洗。合并水层,用浓盐酸酸化至pH4,然后用乙醚彻底再萃取。所成的乙醚萃取液干燥,过滤,滤液蒸发,得5.4克油状物。该5.4克油状物和2.55克碳酸钾于0℃下加到20毫升无水二甲基甲酰胺中。一次加入1.75毫升硫酸二甲酯,让反应温度升至室温,气相色谱分析表明,反应已经完全。反应混合物倾入150毫升水中,并加入10毫升乙醚,白色结晶沉淀析出,滤出结晶。用乙酸乙酯和60-80℃石油醚的混合溶液重结晶,得到(E)2-(2′-苯氧吡啶-3′-基)-3-甲氧基丙烯酸甲酯3.4克;熔点为121-123℃;主要红外峰
(液体石蜡)1710,1635,1575cm-1;1HNMRδ值(CDCl3)3.7(3H,s),3.85(3H,s),6.9-7.45(m),7.60(1H,s),7.5-7.75(m),8.1(m)ppm。
实施例2
该实施例阐明(E)2-(3′-苯氧吡啶-4′-基)-3-甲氧丙烯酸甲酯的制备(表1中的化合物43)。
在氮气流下往10.26克(0.06摩尔)3-苯氧基吡啶与500毫升无水四氢呋喃的溶液中加碘经亚铜和30毫升二甲硫。反应混合物在室温搅拌15分钟,然后冷至-25℃。然后滴加8.0毫升(0.66摩尔)氯甲酸苯酯,产生一暗棕色溶液。10分钟后,在-25℃下滴加20毫升3摩尔浓度的溴化甲基镁溶液(0.066摩尔)。-25℃下搅拌15分钟后,该溶液经1小时升至室温,在这段时间内该溶液已成为清亮的黄色溶液。用150毫升20%的氯化铵水溶液终止反应,然后用250毫升乙醚分配。有机层用20毫升20%氯化铵溶液-氢氧化铵(1∶1)水溶液洗数次,再用10%盐酸、水和盐水洗。乙醚层干燥,蒸发,得一黄色油状物,该油状物再溶于250毫升无水甲苯中。在室温下分批加入15克邻氯醌与100毫升甲苯的混悬液。生成的深色溶液搅拌过夜,然后加入200毫升10%氢氧化钠水溶液,并在室温下继续搅拌10分钟。反应混合物用200毫升乙醚分配,有机层用200毫升10%氢氧化钠水溶液若干份和水洗数次,然后再用10%盐酸(4×250毫升)洗。酸性萃取液用25%氢氧化钠溶液碱化,然后用二氯甲烷萃取4次。合并的二氯甲烷萃取液干燥,蒸发,得到黄色油状物。在100℃,0.05毫巴下球管到球管蒸馏,得到3-苯氧基-4-甲基吡啶6.5克,为一清亮液体,1HNMRδ值(CDCl3)2.25(3H,s),6.9-7.4(6H,m),8.2(1H,s),8.3(1H,d)。
6.1毫升2.6摩尔浓度的正丁基锂的己烷溶液(0.0157摩尔)在-78℃和氮气保护下滴加到搅拌着的3-苯氧基-4-甲基吡啶(2.9克,0.0157摩尔)与20毫升无水四氢呋喃制成的溶液中。生成的棕
色混悬液搅拌30分钟,然后往其中通入一稳定的二氧化碳气流。30分钟后,将反应混合物倾入100毫升水中,并用乙醚萃取2次。水层在60℃下减压蒸发至干。生成的白色固体然后用150毫升氯化氢饱和的甲醇处理,生成的黄色溶液放置过夜。减压除去溶剂,残留物在100毫升二氯甲烷和100毫升碳酸氢盐的饱和水溶液间分配。分离有机层,水层再用二氯甲烷重萃取2次。合并的有机萃取物干燥,蒸发,得到2.5克棕色液体。在140℃0.1毫巴下球管到球管蒸馏,得到2.15克3-苯氧基吡啶-4-基乙酸甲酯,为浅黄色液体;红外峰1735cml-1;1HNMRδ(CDCl3)主要峰3.60(3H,s),3.72(2H,s)。
2.22克(0.01摩尔)三氟甲磺酸三甲基甲硅烷基酯于室温下滴加到1.01克(0.01摩尔)三乙胺与10毫升乙醚制成的溶液中。所成的澄清溶液在0℃下滴加到搅拌着由2.0克(0.00823摩尔)3-苯氧吡啶-4-基乙酸甲酯与10毫升乙醚制成的溶液中。将该两相混合物在室温搅拌1小时,并于室温和氮气下放置过夜。生成的棕色油状物用5毫升二氯甲烷稀释,并转移到滴液漏斗中。在一分离烧瓶中,1.9克(0.01摩尔)四氯化钛溶入10毫升二氯甲烷中,然后在-70℃下滴加到由1.1克(0.01摩尔)原甲酸三甲酯与15毫升二氯甲烷制成的溶液中。在-70℃搅拌下,将预先制好的甲硅烷基烯醇醚滴加到所形成的黄色混悬液中。内温升至-50℃。迅速搅拌反应混合物。使缓慢上升至室温,然后放置过夜。将所成的反应混合物倾入200毫升5%碳酸钾溶液中,然后用乙醚萃取3次。干燥过的乙醚萃取液蒸发,得到棕色油状物。用硅胶层析(乙醚洗脱),得到0.89克标题化合物,为澄清液体;红外峰1700,1630cm-1;1HNMRδ(CDCl3)3.62(3H,s),3.80(3H,s),6.95(2H,m),7.08(1H,m),7.28(3H,m),7.50(1H,s),8.28(1H,m),8.35(1H,m)。
实施例3
该实施例阐明(E)2-(4′-苯氧吡啶-3′-基)-3-甲氧基丙烯酸
0.128克3-(2′-甲亚磺酰基-2′-甲硫乙烯基)-4-苯氧吡啶,为浅黄色胶状物;1HNMRδ值(CDCl3)2.32(3H,s),2.77(3H,s),6.60(1H,d),6.9-7.5(5H,m),7.93(1H,s),8.32(1H,d),9.10(1H,s)。
0.128克(0.42毫摩尔)3-(2′-甲亚磺酰基-2′-甲硫乙烯基)-4-苯氧吡啶溶入氯化氢的甲醇溶液中,溶液在室温下搅拌过夜。这里用的氯化氢的甲醇溶液系由加1.2毫升乙酰氯到12毫升无水甲醇中制得的。将反应混合物蒸发至干,用25毫升碳酸氢钠水溶液搅拌,然后用二氯甲烷萃取2次。合并的萃取液用饱和盐水洗,并蒸去溶剂。经快速柱层析(乙醚洗脱)得到0.066克(4′-苯氧基吡啶-3′-基)乙酸甲酯,为一浅棕色油状物;红外峰(液膜)1580,1740cm-1;1HNMRδ值(CDCl3)3.68(3H,s),3.74(2H,s),6.58(1H,d),7.0-7.5(5H,m),8.3-8.6(2H,m)。
往搅拌着的由0.026克(0.54毫摩尔)汽油洗过的氢化钠(50%,分散于油中)与4毫升二甲基甲酰胺制成的混悬液加入由0.066克(0.27毫摩尔)、(4′-苯氧基吡啶-3′-基)乙酸甲酯、0.39克(6.5毫摩尔)甲酸甲酯与二甲基甲酰胺制成的溶液中。混合物在室温下搅拌3.5小时。于所生成的,几乎澄清的浅黄棕色溶液中滴加0.068克(0.54毫摩尔)硫酸二甲酯与1.5毫升二甲基甲酰胺制成的溶液,并在室温下继续搅拌2.5小时。将反应混合物倾入50毫升饱和盐水中,并用乙醚萃取2次。合并的乙醚萃取液用饱和盐水洗,然后除去溶剂。所得的残留物经快速柱层析分离(乙醚洗脱)得到0.032克2-(4′苯氧基吡啶-3′基)-3-甲氧基丙烯酸甲酯,为浅黄色胶状物;1HNMR(CDCl3)见于表2。
实施例4
本实施例阐明(E)2-(3′-苯氧基吡啶-2′-基)-3-甲氧基丙烯酸甲酯的制备(表1中化合物Ⅰ)。
往一搅拌着的由20克(0.1834摩尔)2-甲基-3-羟基吡啶和40
甲酯(表1中的化合物29)的制备。
2.89克(25.5毫摩尔)4-氯吡啶与15毫升四氢呋喃制成的溶液在-78℃下,加到搅拌着的二异丙基氨基锂的溶液中,后者是通过把10.2毫升2.5摩尔浓度(25.5毫摩尔)正丁基锂在-78℃下加到2.58克(25.5毫摩尔)二异丙胺和无水四氢呋喃的溶液中制得的。2小时后,在-78℃下,加入由2.05克(28.1毫摩尔)二甲基甲酰胺与25毫升四氢呋喃制成的溶液。在-78℃下再反应1小时后,使反应混合物缓慢升至室温(经过16小时)。所成的溶液倾入200毫升饱和盐水中,并用乙醚萃取(每次100毫升,共3次)。合并的乙醚萃取液用饱和盐水洗,然后蒸发溶剂。残留物用快速柱层析(汽油-乙醚洗脱),得2.86克固体4-氯-3-吡啶甲醛,熔点为53-54℃;红外峰(液体石蜡)1580,1695cm-1;1HNMRδ值(CDCl3)7.45(1H,d),8.70(1H,d),9.07(1H,s),10.50(1H,s)。
1.34克(14.3毫摩尔)苯酚与25毫升二甲基甲酰胺制成的溶液与0.99克(7.2毫摩尔)无水碳酸钾在70-80℃下搅拌40分钟。往里加2.02克(14.3毫摩尔)4-氯-3-吡啶甲醛和0.10克青铜粉,所得的混悬液在100-110℃搅拌2小时。冷却反应混合物,过滤,残渣用乙醚洗。合并的乙醚洗涤液用乙醚稀释至400毫升,用饱和盐水洗4次,除去溶剂,得到2.62克4-苯氧基-3-吡啶甲醛,为浅黄色结晶固体;熔点为74-75℃;红外峰(液体石蜡)1590,1695,2760cm-1;1HNMRδ值(CDCl3)6.75(1H,宽峰)7.15(2H,d),7.35(1H,t),7.50(2H,t),8.5-9.7(2H,宽峰),10.7(1H,s)。
往一搅拌着的由0.687克(3.45毫摩尔)4-苯氧基-3-吡啶甲醛。0.429克(3.45毫摩尔)单甲硫基二甲基亚砜和四氢呋喃制成的溶液中,滴加0.53毫升40%三通B的甲醇溶液。混合物加热回流2小时,使冷却,然后用150毫升二氯甲烷稀释。该溶液用饱和盐水洗2次,蒸除溶剂。残留物经快速柱层析(乙醚-乙酸乙酯洗脱),得到
毫升二甲基甲酰胺制成的溶液中加7.4克氢氧化钠,1克青铜和38.7毫升(0.367摩尔)溴苯。将反应混合物加热至153℃,过夜,在此期间,40毫升挥发性组份由反应混合物中蒸出,蒸出的挥发性组份用溴苯补充。反应混合物在乙醚和水之间分配,乙醚层用水洗,干燥,蒸发,得到13克棕色油状物。在150℃,0.5毫米汞柱下球管到球管蒸馏。各到5克2-甲基-3-苯氧基吡啶,为无色油状物,1HNMR表明其中染有微量二甲基甲酰胺。该油状物再溶于乙醚,水洗,干燥蒸发,得到3.6克2-甲基-3-苯氧基吡啶,为清亮无色的油状物;1HNMRδ值(CDCl3)2.52(3H,s),6.84-7.44(7H,m),8.78(1H,m)。
在-60℃下,通过注射器往搅拌着的由3.2克(0.017摩尔)2-甲基-3-苯氧基吡啶与25毫升四氢呋喃制成的溶液中加7毫升2.5摩尔浓度的正丁基锂的己烷溶液,进料时间为15分钟。立即形成深红色,并有轻微放热。再搅拌20分钟后,将二氧化碳气体通入反应混合物中。发生温和的放热反应,生成膏状沉淀,使反应混合物升温至室温,时间为2小时,用水100毫升稀释,然后用二氯甲烷萃取2次,用乙醚萃取1次。水相在真空下50℃蒸发,形成的乳色残留物再溶入氯化氢的甲醇溶液中[氯化氢的甲醇溶液通过将10毫升乙酰氯溶入100毫升甲醇制得],室温放置过夜。真空下除去溶剂,残留物再溶入二氯甲烷中,并用稀碳酸氢钠溶液洗。有机层经干燥、蒸发,得油状残留物。层析分离(二氯甲烷-乙醚洗脱),得1.5克(3-苯氧基吡啶-2-基)乙酸甲酯,为棕色油状物;红外峰(液膜)1735,1400,1250cm-1。
1克(3-苯氧基吡啶-2-基)乙酸甲酯溶于25毫升原甲酸三甲酯和醋酐的混合物中,并加入催化量的无水氯化锌。所成的反应混合物在回流下搅拌3小时。等分试样的气相色谱分析表明,在原料消失的同时,有两个新产物生成。将深棕色的反应混合物冷却,并在真空下蒸发至干。残留物在乙醚和稀碳酸氢钠水溶液之间分配。将乙醚层
干燥、蒸发,得到1.26克棕色油状残留物。层析分离(乙醚-二氯甲烷,1∶1混合液洗脱),得到730毫克3,3-二甲氧基-2-(3′-苯氧基吡啶-2′-基)丙酸甲酯,为一黄色油状物;红外峰(液膜)1735,1440,1245,1070,750cm-1;1HNMRδ值(CDCl3)3.24(3H,s),3.45(3H,s),3.60(3H,s),4.65(1H,d);5.38(1H,d);和210毫克(E)2-(3′-苯氧基吡啶-2′-基)-3-甲氧基丙烯酸甲酯,黄色油状物,红外峰(液膜)1710,1635,1435,1260,1130cm-1;1HNMRδ值(CDCl3)3.60(3H,s),3.76(3H,s),6.85-7.40(7H,m),7.56(1H,s),8.44(1H,t);m/e285(M+),270,254,226。
实施例5
本实施例阐明(E)2-(2′-苯氧甲基吡啶-3′-基)-3-甲氧基丙烯酸甲酯的制备(表1中的化合物67)。
在0℃下往一搅拌着的0.62克氢化钠(60%,分散在油中)与15毫升二甲基甲酰胺的混悬液中滴加由1.968克(2-甲基吡啶-3-基)乙酸甲酯、3.6克甲酸甲酯和5毫升二甲基甲酰胺配成的溶液。将反应液在室温搅拌30分钟,然后放置过夜。反应混合物倾入250毫升水中,并用100毫升乙醚萃取。水层用稀盐酸调至pH7,然后用乙酸乙酯(3×100毫升)萃取。合并有机萃取物,干燥,减压蒸发,得到2.83克2-(2′-甲基吡啶-3′-基)-3-羟基丙烯酸甲酯,为棕色油状物,NMR表明其中含58%二甲基甲酰胺。该2.83克粗油状物与1.59克硫酸二甲酯及3.31克碳酸钾在40毫升二甲基甲酰胺中室温搅拌30分钟,然后放置过夜。反应混合物倾入300毫升水中,溶液用稀盐酸调至PH8,然后用乙酸乙酯(3×200毫升)萃取。合并的有机层用水洗3次,每次用水50毫升,然后干燥,减压蒸发,得到0.72克(E)2-(2′-甲基吡啶-3′-基)-3-甲氧基丙烯酸甲酯,为一黄色液体。红外峰1717,1640,1260cm-1;1HNMRδ值(CDCl3)2.41(3H,s),3.71(3H,s),3.85(3H,s),7.12
(1H,m),7.41(1H,d),7.59(1H,s),8.44(1H,d)ppm。
0.72克(E)2-(2′-甲基吡啶-3′-基)-3-甲氧基丙烯酸甲酯、0.84克N-溴代琥珀酰亚胺及0.025克偶氮异丁腈(催化剂)在25毫升四氯化碳中搅拌,然后加热回流3.5小时。反应混合物在100毫升饱和碳酸氢钠溶液和120毫升乙酸乙酯间分配。水层用(2×30毫升)乙酸乙酯再萃取。合并的有机层用20毫升水洗,然后干燥,减压蒸发,得1.14克(E)2-(2′-溴甲基吡啶-3′-基)-3-甲氧基丙烯酸甲酯,为棕色油状物,该油状物不经进一步纯化即可使用。该油状物溶于5毫升二甲基甲酰胺并加到一搅拌着的0.41克苯酚钠和5毫升二甲基甲酰胺制成的溶液中,然后室温搅拌30分钟并放置64小时。反应混合物倾入200毫升水中,并用乙酸乙酯(3×100毫升)萃取。合并的有机层用水(2×30毫升)洗,干燥,减压蒸发,得到0.97克棕色油状物。该油状物用HPLC纯化(乙酸乙酯洗脱),得到0.194克(E)2-(2′-苯氧甲基吡啶-3′-基)-3-甲氧基丙烯酸甲酯,为淡棕色油状物,红外峰(液膜)1715,1640,1260,1135cm-1;1HNMRδ(CDCl3)3.66(3H,s),3.76(3H,s),5.12(2H,s),6.82-6.98(3H,m),7.16-7.32(3H,m),7.51(1H,d),7.53(1H,s),8.6(1H,d)ppm。
以下是适合于农业和园艺目的能由本发明的化合物配制的制剂的实施例,百分比为重量百分比。
实施例6
将各组分混合并搅拌,直至全部溶解,制得一可乳化的浓缩物。
化合物15 10%
苄醇 30%
十二烷基苯磺酸钙 5%
壬基苯酚乙氧基醚(13摩尔环氧乙烷) 10%
烷基苯 45%
实施例7
活性成分溶于二氯甲烷中,所得溶液喷撒到硅镁土颗粒上。然后让溶剂蒸发,得到一颗粒制剂。
化合物15 5%
硅镁土颗粒 95%
实施例8
通过研磨和混合下面三种成分,制得一种适于拌种用的制剂。
化合物15 50%
矿物油 2%
陶土 48%
实施例9
把活性成分与滑石研磨并混合,制得一种可粉尘化的粉剂。
化合物15 5%
滑石 95%
实施例10
通过球磨下述成分使形成含水悬浮液制得一浓缩悬浮剂。
化合物15 40%
木素磺酸钠 10%
膨润粘土 1%
水 49%
该制剂可以用水稀释用作喷雾剂或直接用于种子上。
实施例11
把下述组合混合并研磨,直至全部彻底混合,制得一可湿性粉剂。
化合物15 25%
十二烷基硫酸钠 2%
木素磺酸钠 5%
硅石 25%
陶土 43%
实施例12
以化合物进行抗植物的各种叶真菌疾病试验。应用的技术如下。
植物长在4厘米直径的小盆中的John Innes盆栽混合肥内(1号或2号)。测定的化合物或用水性散胶T珠磨配制,或用丙酮或丙酮/乙醇溶液,该溶液在临用前立即稀释成所需要的浓度。对于叶子的疾病,该制剂(100ppm活性成分)喷洒到叶子上并用于土壤中的植物的根上。使用喷雾剂时达到极大滞留,根部浸透的最后的浓度相当于大约40ppm活性成份/干土壤。当该喷雾剂用于谷类时,为得到最终浓度为0.05%,可加入吐温20。
对于大部分试验,都是在植物接种上病菌的前一天或两天将化合物用于土壤(根)和叶(通过喷雾)。一个例外是对禾草白粉菌的试验,在这个试验中,植物在处理前24小时接种上病菌。叶病原体作为孢子悬浮液通过喷雾施用于试验植物的叶子上。接种之后,试验植物置于一适宜的环境中使发生感染,然后孵育,直到疾病发展到可以评价为止。接种到评价之间的这段时间,根据疾病和环境从4天至14天不等。
用下面的等级记录疾病对照:
4=无疾病
3=在未处理的植物上有微量至5%染病
2=在未处理的植物上有6至25%染病
1=在未处理的植物上有26至59%染病
0=在未处理的植物上有60至100%染病
结果列于表3中。
实施例13
该实施例阐明表1中的化合物15,16,19,20,23和43的植物生长调节性能。
凭借整体植物筛选测定这些化合物对6个植物种的植物生长调节活性。在该筛分中使用的植物种与叶期列在表Ⅳ中,在该叶期对植物
喷洒化合物。
每种化合物的制剂采用履带喷雾机及SS8004ET形喷嘴按4000ppm(4千克/公顷,按每公顷土地1000升的容量)施用。对西红柿按2000和500ppm做了附加试验。
喷哂以后,植物在温室中生长,白天的温度为25℃,夜间的温度为22℃。一些例外是温带的谷类小麦和大麦,它们生长的温度是白天13-16℃,夜间11-13℃。必要时,提供平均为16小时的(最小为14小时)补充光照。
在温室中2至6周以后,根据植物种和时节,就其形态特征,以喷洒空白制剂的植物作对照,对试验植物进行直观评价。结果示于表Ⅴ中。
关键词
*2000ppm+500ppm
延迟发育1-3,其中1=10-30%
2=21-60%
3=61-100%
绿色效应=G
顶点伤害=A
长新芽或侧枝=T
空白意味着效应小于10%
NT表明该化合物对这一个品种未进行试验。
“ph”为苯基
*β-甲氧基丙烯酸酯基上烯质子的单峰的化学位移(ppm,TMS为内标),氘代氯仿作溶剂。
表2中选择列出了表1中的一些化合物的1HNMR数据。化学位移的单位为ppm,TMS为内标,均用氘代氯仿作溶剂进行测定。使用了下述缩写:
br=宽峰 t=三重峰
s=单峰 q=四重峰
d=双峰 m=多重峰
J=偶合常数 Hz=赫兹
表2 选择的1HNMR数据
化合物号1HNMR数据
1 3.60(3H,s);3.76(3H,s);6.85-7.40(7H,m);
7.56(1H,s);8.44(1H,t).
21 3.55(3H,s);3.69(3H,s);6.94(1H,d);
7.06(2H,d);7.45-7.60(3H,m);7.50(1H,s);
8.0(1H,m).
23 3.68(3H,s);3.86(3H,s);6.98-7.18(4H,m);
7.20-7.32(1H,m);7.58(1H,s);7.62-7.66
(1H,m);8.10-8.14(1H,m).
29 3.71(3H,s);3.88(3H,s);6.70(1H,d);7.06
(2H,d);7.23(1H,t);7.40(2H,m);7.64
(1H,s);8.35(1H,d);8.43(1H,s).
表2 选择的1HNMR数据(续)
化合物号1HNMR数据
43 3.62(3H,s);3.80(3H,s);6.95(2H,m);7.08
(1H,m);7.28(1H,m);7.50(1H,s);8.28
(1H,m);8.35(1H,m).
57 3.69(3H,s);3.86(3H,s);6.80-6.90(3H);
7.05(1H);7.25-7.35(1H)7.59(1H,s);7.65
(1H);8.13(1H)
63 3.70(3H,s);3.87(3H,s);6.9-7.4(3H,m);
7.46(1H,d);7.61(1H,s);7.68(1H,q);8.16
(1H,q).
100 2.41(3H,s);3.71(3H,s);3.85(3H,s);7.12
(1H,d);7.59(1H,s);8.44(1H,d).
106 3.74(3H,s);3.99(3H,s);6.98(1H,m);7.12
(1H,m);7.48(1H,m);8.02(1H,s);8.38
(1H,m).
具有通式(Ⅰ)的本发明的化合物能通过图1、图2和图3中所列出的化学方法制备。图1、图2和图3中的R1、R2、Z、A、B、D和E都具有前面的定义,G为氢或金属原子(例如钠原子)、M为金属原子(例如锂原子)或一金属原子加上一个缔合的卤原子(例如MgI、MgBr、或MgCl)而且L为卤原子或其它优良的离去基。
表 ④-Ⅳ
用于整体植物筛选的植物
种 符号 品种 处理时的 每3″盆 混合肥
生长期 中植物数 料类型
大麦 BR Atem 1-1.5leaves 4 JIP*
小麦 WW Timmo 1-1.5leaves 4 JIP
玉米 MZ Earliking 2 1/4 -2 1/2 leaves 1 PEAT
苹果 AP Red Delicious 4-5leaves 1 JIP
水稻 RC Ishikari 2-2 1/2 leaves 4 JIP
西红柿 TO Ailsa.Craig 2-2 1/2 leaves 1 PEAT
*John Innes盆栽混合肥
表 ⑤-Ⅴ
化合物号 表 BR WW RC AP MZ TO TO*TO+
5 I I NT NT NT
16 I NT NT NT NT NT NT
19 I NT NT NT 2GAT NT I
20 I NT NT NT NT NT NT I
23 I NT IG NT NT I I 2G
43 I 2T T T I G NT I
关键词
*2000ppm,+500ppm
延迟发育1-3,其中1=10-30%
2=21-60%
Claims (11)
2、根据权利要求1的组合物,R1和R2都是甲基。
3、根据权利要求1的组合物,A是除了氢以外的取代基并且在吡啶环上的烷氧基丙烯酸酯的邻位。
4、根据权利要求1的组合物,其中R1和R2均为甲基,A在烷氧基丙烯酸酯的邻位,为苯氧基或用卤素,C1-4烷基、C1-4烷氧基、三氟甲基三氟甲氧基、氰基、苯基或苯氧基取代的苯氧基。
5、根据权利要求1-4中任一项的组合物,其中A在吡啶环的2位,所述烷氧基丙烯酸酯在吡啶环的3-位。
6、根据权利要求1-4中任一项的组合物,它是杀真菌组合物。
7、根据权利要求1-4中任一项的组合物,它是杀真菌组合物,并且其中A在吡啶环的2位,所述烷氧基丙烯酸酯在吡啶的3-位。
8、应用权利要求1的组合物杀真菌,包括向植物或种子或其所在场所施用权利要求1的组合物。
9、应用权利要求1的组合物杀死或控制昆虫或线虫,包括向昆虫或线虫或其所在地施用有效量的权利要求1的杀昆虫或杀线虫组合物。
10、应用权利要求1的组合物调节植物生长,包括向植物或植物种子或其所在地施用权利要求1的调节植物生长的组合物。
11、制备权利要求1的农用组合物的方法,包括将权利要求1所定义的式(Ⅰ)化合物与农业上适应的稀释剂或载体混合,其中式Ⅰ化合物制备如下,
(ⅰ)用式R2L的化合物在适当的溶剂中处理其中G为金属原子的式(Ⅲ)的化合物,或用一种碱和一种R2L化合物在适当的溶剂中处理G为氢的式(Ⅲ)化合物,
其中A,R1和R2如权利要求1中所限定,L为离去基团,或
(ⅱ)在酸性或碱性条件下从式(Ⅻ)化合物中除去链烷醇R2OH,
其中A,R1和R2如权利要求1中所限定,
(ⅲ)在碱存在下使式(ⅩⅤ)的化合物在适当的溶剂中与一种可被卤素,C1-4烷基,C1-4烷氧基,三氟甲基,三氟甲氧基,氰基,苯基或苯氧基任意取代的苯酚反应制备其中A为可被囟素,C1-4烷基,C1-4烷氧基,三氟甲基,三氟甲氧基,氰基,苯基或苯氧基任意取代的苯氧基(C1-4)烷基的式(Ⅰ)化合物;
其中R1和R2的定义同权利要求1,R5为氢或C1-3烷基,L是一种离去基团。
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB868609456A GB8609456D0 (en) | 1986-04-17 | 1986-04-17 | Fungicides |
GB8609456 | 1986-04-17 | ||
GB878701627A GB8701627D0 (en) | 1987-01-26 | 1987-01-26 | Fungicides |
GB8701627 | 1987-01-26 |
Publications (2)
Publication Number | Publication Date |
---|---|
CN87103544A CN87103544A (zh) | 1988-04-06 |
CN1022885C true CN1022885C (zh) | 1993-12-01 |
Family
ID=26290649
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN87103544A Expired - Lifetime CN1022885C (zh) | 1986-04-17 | 1987-04-17 | 含有丙烯酸衍生物作为活性成分的农用组合物,其应用制备方法 |
Country Status (14)
Country | Link |
---|---|
US (2) | US4826531A (zh) |
EP (1) | EP0243012B1 (zh) |
JP (1) | JPH0819102B2 (zh) |
KR (1) | KR950003924B1 (zh) |
CN (1) | CN1022885C (zh) |
AU (1) | AU609036B2 (zh) |
CA (1) | CA1288094C (zh) |
DE (1) | DE3783503T2 (zh) |
DK (1) | DK164595C (zh) |
ES (1) | ES2053533T3 (zh) |
GR (1) | GR3006778T3 (zh) |
HU (1) | HU203874B (zh) |
NZ (1) | NZ219858A (zh) |
PH (1) | PH23535A (zh) |
Families Citing this family (26)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5258360A (en) * | 1986-04-17 | 1993-11-02 | Imperial Chemical Industries Plc | Alphamethoxy acrylic acid derivatives as fungicides |
GB8609452D0 (en) * | 1986-04-17 | 1986-05-21 | Ici Plc | Fungicides |
US5198444A (en) * | 1987-04-17 | 1993-03-30 | Imperial Chemical Industries Plc | Methyl α-(2-substituted)pyrid-3-yl-β-methoxyacrylates, compositions containing them and their use as fungicides |
GB8724252D0 (en) * | 1987-10-15 | 1987-11-18 | Ici Plc | Fungicides |
GB8724251D0 (en) * | 1987-10-15 | 1987-11-18 | Ici Plc | Chemical process |
US5264440A (en) * | 1989-02-10 | 1993-11-23 | Imperial Chemical Industries Plc | Fungicides |
DE3904931A1 (de) * | 1989-02-17 | 1990-08-23 | Bayer Ag | Pyridyl-substituierte acrylsaeureester |
GB8908875D0 (en) * | 1989-04-19 | 1989-06-07 | Ici Plc | Fungicides |
DK0463488T4 (da) * | 1990-06-27 | 2004-05-10 | Basf Ag | 0-benzyloximethere og plantebeskyttelsesmidler indeholdende disse forbindelser |
CN1038249C (zh) * | 1991-08-28 | 1998-05-06 | 罗姆和哈斯公司 | 含有二氢哒嗪酮及其相关化合物的杀菌组合物 |
GB9218241D0 (en) * | 1992-08-27 | 1992-10-14 | Ici Plc | Chemical process |
ZA938081B (en) * | 1992-10-30 | 1995-05-02 | Basf Corp | Granular water soluble or hygroscopic agricultural formulations and methods of making them |
US5380350A (en) * | 1992-10-30 | 1995-01-10 | Basf Corporation | Methods of making granular water soluble or hygroscopic agricultural formulations |
GB9314355D0 (en) * | 1993-07-12 | 1993-08-25 | Sandoz Ltd | Novel compounds |
GB9400889D0 (en) * | 1994-01-18 | 1994-03-16 | Sandoz Ltd | Novel compounds |
IL115889A0 (en) * | 1994-11-14 | 1996-01-31 | Rohm & Haas | Pyridazinones and their use as fungicides |
US5783580A (en) * | 1995-01-10 | 1998-07-21 | Sandoz, Ltd. | α-pyrimidinyl acrylic acid derivatives |
DE19500758A1 (de) * | 1995-01-13 | 1996-07-18 | Basf Ag | Substituierte 2-Phenylpyridine |
DE19500911A1 (de) * | 1995-01-13 | 1996-07-18 | Basf Ag | Substituierte 2-Phenylpyridine |
GB9519787D0 (en) * | 1995-09-28 | 1995-11-29 | Sandoz Ltd | Organic compounds |
US6200933B1 (en) | 1996-12-26 | 2001-03-13 | Kureha Kagaku Kabushiki Kaisha | 6-(Nonsubstituted or substituted) phenoxy picolinic acids, process of preparing the same, and agricultural/horticultural germicides containing the same |
US6306866B1 (en) * | 1998-03-06 | 2001-10-23 | American Cyanamid Company | Use of aryl-substituted pyrimidines as insecticidal and acaricidal agents |
WO2012087980A1 (en) | 2010-12-21 | 2012-06-28 | Agraquest, Inc. | Sandpaper mutants of bacillus and methods of their use to enhance plant growth, promote plant health and control diseases and pests |
MX2014002890A (es) | 2011-09-12 | 2015-01-19 | Bayer Cropscience Lp | Metodo para mejorar la salud y/o promover el crecimiento de una planta y/o mejorar la maduracion de frutos. |
CN102796502B (zh) * | 2012-09-11 | 2014-02-19 | 西华师范大学 | 缓蚀剂溴化-n-烷基吡啶丙烯酸酯及其制备方法 |
CN105017134A (zh) * | 2015-07-26 | 2015-11-04 | 陈吉美 | 一种4-吡啶丙烯酸的制备方法 |
Family Cites Families (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
SE8204879D0 (sv) * | 1982-08-26 | 1982-08-26 | Haessle Ab | Novel chemical intermediates |
CA1234388A (en) * | 1982-09-27 | 1988-03-22 | Pieter T. Haken | Fungicidally active compositions containing ethene derivatives |
NZ213630A (en) * | 1984-10-19 | 1990-02-26 | Ici Plc | Acrylic acid derivatives and fungicidal compositions |
DE3519282A1 (de) * | 1985-05-30 | 1986-12-04 | Basf Ag, 6700 Ludwigshafen | Acrylsaeureester und fungizide, die diese verbindungen enthalten |
DE3519280A1 (de) * | 1985-05-30 | 1986-12-04 | Basf Ag, 6700 Ludwigshafen | Stilbenderivate und fungizide, die diese verbindungen enthalten |
EP0242070A3 (en) * | 1986-04-17 | 1988-12-28 | Imperial Chemical Industries Plc | Phenyl-acrylic acid ester derivatives, process for their preparation and their use as fungicides |
DE3789117T2 (de) * | 1986-04-17 | 1994-05-26 | Zeneca Ltd | Fungizide. |
-
1987
- 1987-03-30 EP EP87302738A patent/EP0243012B1/en not_active Expired - Lifetime
- 1987-03-30 DE DE8787302738T patent/DE3783503T2/de not_active Expired - Lifetime
- 1987-03-30 ES ES87302738T patent/ES2053533T3/es not_active Expired - Lifetime
- 1987-04-02 NZ NZ219858A patent/NZ219858A/xx unknown
- 1987-04-09 AU AU71355/87A patent/AU609036B2/en not_active Ceased
- 1987-04-10 PH PH35124A patent/PH23535A/en unknown
- 1987-04-10 DK DK187687A patent/DK164595C/da not_active IP Right Cessation
- 1987-04-13 KR KR1019870003495A patent/KR950003924B1/ko not_active IP Right Cessation
- 1987-04-15 HU HU871656A patent/HU203874B/hu not_active IP Right Cessation
- 1987-04-17 US US07/039,401 patent/US4826531A/en not_active Expired - Lifetime
- 1987-04-17 CN CN87103544A patent/CN1022885C/zh not_active Expired - Lifetime
- 1987-04-17 JP JP9347687A patent/JPH0819102B2/ja not_active Expired - Lifetime
- 1987-04-21 CA CA000535189A patent/CA1288094C/en not_active Expired - Fee Related
-
1988
- 1988-12-30 US US07/292,308 patent/US5112386A/en not_active Expired - Lifetime
-
1993
- 1993-01-14 GR GR920402599T patent/GR3006778T3/el unknown
Also Published As
Publication number | Publication date |
---|---|
ES2053533T3 (es) | 1994-08-01 |
DK164595B (da) | 1992-07-20 |
US5112386A (en) | 1992-05-12 |
US4826531A (en) | 1989-05-02 |
PH23535A (en) | 1989-08-25 |
CN87103544A (zh) | 1988-04-06 |
JPH0819102B2 (ja) | 1996-02-28 |
JPS62255478A (ja) | 1987-11-07 |
HU203874B (en) | 1991-10-28 |
HUT43240A (en) | 1987-10-28 |
EP0243012A2 (en) | 1987-10-28 |
KR950003924B1 (ko) | 1995-04-20 |
DE3783503D1 (de) | 1993-02-25 |
AU7135587A (en) | 1987-10-22 |
DK187687D0 (da) | 1987-04-10 |
DE3783503T2 (de) | 1993-05-13 |
EP0243012B1 (en) | 1993-01-13 |
DK164595C (da) | 1992-12-07 |
KR870010000A (ko) | 1987-11-30 |
NZ219858A (en) | 1989-10-27 |
GR3006778T3 (zh) | 1993-06-30 |
DK187687A (da) | 1987-10-18 |
AU609036B2 (en) | 1991-04-26 |
CA1288094C (en) | 1991-08-27 |
EP0243012A3 (en) | 1989-01-11 |
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