CN1032794A - 盐 - Google Patents
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- Publication number
- CN1032794A CN1032794A CN88104364A CN88104364A CN1032794A CN 1032794 A CN1032794 A CN 1032794A CN 88104364 A CN88104364 A CN 88104364A CN 88104364 A CN88104364 A CN 88104364A CN 1032794 A CN1032794 A CN 1032794A
- Authority
- CN
- China
- Prior art keywords
- formula
- compound
- fontanel
- alkoxyl group
- phenyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
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- 150000003839 salts Chemical class 0.000 title abstract description 6
- 150000001875 compounds Chemical class 0.000 claims abstract description 42
- 239000000203 mixture Substances 0.000 claims abstract description 32
- 238000000034 method Methods 0.000 claims abstract description 17
- 125000000547 substituted alkyl group Chemical group 0.000 claims abstract description 14
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 13
- 230000000855 fungicidal effect Effects 0.000 claims abstract description 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 12
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 7
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 4
- 230000005764 inhibitory process Effects 0.000 claims abstract description 4
- -1 methoxyl group Chemical group 0.000 claims description 18
- 239000004480 active ingredient Substances 0.000 claims description 14
- 229910052801 chlorine Inorganic materials 0.000 claims description 9
- 238000002360 preparation method Methods 0.000 claims description 9
- 125000004429 atom Chemical group 0.000 claims description 8
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 6
- 239000013543 active substance Substances 0.000 claims description 6
- 239000000460 chlorine Substances 0.000 claims description 6
- 150000002500 ions Chemical class 0.000 claims description 6
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 5
- 229910052794 bromium Inorganic materials 0.000 claims description 5
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 2
- 241000233866 Fungi Species 0.000 claims description 2
- 150000001450 anions Chemical class 0.000 claims description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 239000000969 carrier Substances 0.000 claims description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000001207 fluorophenyl group Chemical group 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 125000003944 tolyl group Chemical group 0.000 claims description 2
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 2
- 230000001954 sterilising effect Effects 0.000 claims 1
- 238000004659 sterilization and disinfection Methods 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 abstract description 4
- 125000001188 haloalkyl group Chemical group 0.000 abstract 2
- 125000005843 halogen group Chemical group 0.000 abstract 1
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 24
- 241000219095 Vitis Species 0.000 description 15
- 235000009754 Vitis X bourquina Nutrition 0.000 description 14
- 235000012333 Vitis X labruscana Nutrition 0.000 description 14
- 235000014787 Vitis vinifera Nutrition 0.000 description 14
- 239000003795 chemical substances by application Substances 0.000 description 13
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 239000000463 material Substances 0.000 description 7
- 239000000843 powder Substances 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- 241000196324 Embryophyta Species 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 6
- 239000006185 dispersion Substances 0.000 description 6
- 239000000654 additive Substances 0.000 description 5
- 230000000996 additive effect Effects 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 241000123650 Botrytis cinerea Species 0.000 description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 4
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 239000013504 Triton X-100 Substances 0.000 description 4
- 229920004890 Triton X-100 Polymers 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 239000007859 condensation product Substances 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 239000000839 emulsion Substances 0.000 description 4
- 150000004714 phosphonium salts Chemical class 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 238000009736 wetting Methods 0.000 description 4
- 239000005995 Aluminium silicate Substances 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- 235000012211 aluminium silicate Nutrition 0.000 description 3
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 3
- 230000008025 crystallization Effects 0.000 description 3
- 239000012466 permeate Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 159000000000 sodium salts Chemical class 0.000 description 3
- 239000002689 soil Substances 0.000 description 3
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical class C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 description 2
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 2
- OKPUICCJRDBRJT-UHFFFAOYSA-N 4-chlorobenzenecarbothioamide Chemical compound NC(=S)C1=CC=C(Cl)C=C1 OKPUICCJRDBRJT-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
- 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 2
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 2
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 241000220317 Rosa Species 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 2
- QIOZLISABUUKJY-UHFFFAOYSA-N Thiobenzamide Chemical compound NC(=S)C1=CC=CC=C1 QIOZLISABUUKJY-UHFFFAOYSA-N 0.000 description 2
- YKTSYUJCYHOUJP-UHFFFAOYSA-N [O--].[Al+3].[Al+3].[O-][Si]([O-])([O-])[O-] Chemical compound [O--].[Al+3].[Al+3].[O-][Si]([O-])([O-])[O-] YKTSYUJCYHOUJP-UHFFFAOYSA-N 0.000 description 2
- 229910000323 aluminium silicate Inorganic materials 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 2
- 239000004359 castor oil Substances 0.000 description 2
- 235000019438 castor oil Nutrition 0.000 description 2
- 230000009194 climbing Effects 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 239000004495 emulsifiable concentrate Substances 0.000 description 2
- 239000003995 emulsifying agent Substances 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 230000009969 flowable effect Effects 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 235000013305 food Nutrition 0.000 description 2
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 2
- 229910000037 hydrogen sulfide Inorganic materials 0.000 description 2
- 239000012442 inert solvent Substances 0.000 description 2
- 150000002632 lipids Chemical class 0.000 description 2
- 229940043265 methyl isobutyl ketone Drugs 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 239000012188 paraffin wax Substances 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 2
- 239000004546 suspension concentrate Substances 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-O triphenylphosphanium Chemical compound C1=CC=CC=C1[PH+](C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-O 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- 239000000080 wetting agent Substances 0.000 description 2
- KTZDPHCMZMVFDT-UHFFFAOYSA-M (2-ethoxycarbonyl-1,3-thiazol-4-yl)methyl-triphenylphosphanium;bromide Chemical compound [Br-].S1C(C(=O)OCC)=NC(C[P+](C=2C=CC=CC=2)(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 KTZDPHCMZMVFDT-UHFFFAOYSA-M 0.000 description 1
- MEIRRNXMZYDVDW-MQQKCMAXSA-N (2E,4E)-2,4-hexadien-1-ol Chemical compound C\C=C\C=C\CO MEIRRNXMZYDVDW-MQQKCMAXSA-N 0.000 description 1
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 description 1
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 1
- SUNMBRGCANLOEG-UHFFFAOYSA-N 1,3-dichloroacetone Chemical compound ClCC(=O)CCl SUNMBRGCANLOEG-UHFFFAOYSA-N 0.000 description 1
- CBQDTCDOVVBGMN-UHFFFAOYSA-N 2-methyl-3-octylphenol Chemical compound CCCCCCCCC1=CC=CC(O)=C1C CBQDTCDOVVBGMN-UHFFFAOYSA-N 0.000 description 1
- DUIOKRXOKLLURE-UHFFFAOYSA-N 2-octylphenol Chemical compound CCCCCCCCC1=CC=CC=C1O DUIOKRXOKLLURE-UHFFFAOYSA-N 0.000 description 1
- FOGYNLXERPKEGN-UHFFFAOYSA-N 3-(2-hydroxy-3-methoxyphenyl)-2-[2-methoxy-4-(3-sulfopropyl)phenoxy]propane-1-sulfonic acid Chemical compound COC1=CC=CC(CC(CS(O)(=O)=O)OC=2C(=CC(CCCS(O)(=O)=O)=CC=2)OC)=C1O FOGYNLXERPKEGN-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 241000370738 Chlorion Species 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- 235000005979 Citrus limon Nutrition 0.000 description 1
- 244000131522 Citrus pyriformis Species 0.000 description 1
- 244000205754 Colocasia esculenta Species 0.000 description 1
- 235000006481 Colocasia esculenta Nutrition 0.000 description 1
- 241001124144 Dermaptera Species 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 1
- 244000207740 Lemna minor Species 0.000 description 1
- 235000006439 Lemna minor Nutrition 0.000 description 1
- 238000005684 Liebig rearrangement reaction Methods 0.000 description 1
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 1
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 description 1
- 244000131316 Panax pseudoginseng Species 0.000 description 1
- 235000005035 Panax pseudoginseng ssp. pseudoginseng Nutrition 0.000 description 1
- 235000003140 Panax quinquefolius Nutrition 0.000 description 1
- CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical group ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 description 1
- 235000001855 Portulaca oleracea Nutrition 0.000 description 1
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
- 239000004141 Sodium laurylsulphate Substances 0.000 description 1
- 229920002125 Sokalan® Polymers 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 1
- 239000005864 Sulphur Substances 0.000 description 1
- 240000001085 Trapa natans Species 0.000 description 1
- 235000009392 Vitis Nutrition 0.000 description 1
- 239000001089 [(2R)-oxolan-2-yl]methanol Substances 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 125000003282 alkyl amino group Chemical group 0.000 description 1
- 125000002877 alkyl aryl group Chemical group 0.000 description 1
- 125000004644 alkyl sulfinyl group Chemical group 0.000 description 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 1
- SNAAJJQQZSMGQD-UHFFFAOYSA-N aluminum magnesium Chemical compound [Mg].[Al] SNAAJJQQZSMGQD-UHFFFAOYSA-N 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 1
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 1
- 235000011130 ammonium sulphate Nutrition 0.000 description 1
- 239000003945 anionic surfactant Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 229910052789 astatine Inorganic materials 0.000 description 1
- RYXHOMYVWAEKHL-UHFFFAOYSA-N astatine atom Chemical compound [At] RYXHOMYVWAEKHL-UHFFFAOYSA-N 0.000 description 1
- 229960000892 attapulgite Drugs 0.000 description 1
- JXLHNMVSKXFWAO-UHFFFAOYSA-N azane;7-fluoro-2,1,3-benzoxadiazole-4-sulfonic acid Chemical compound N.OS(=O)(=O)C1=CC=C(F)C2=NON=C12 JXLHNMVSKXFWAO-UHFFFAOYSA-N 0.000 description 1
- 229910052728 basic metal Inorganic materials 0.000 description 1
- 150000003818 basic metals Chemical class 0.000 description 1
- 235000013871 bee wax Nutrition 0.000 description 1
- 239000012166 beeswax Substances 0.000 description 1
- 229940073608 benzyl chloride Drugs 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- YYRMJZQKEFZXMX-UHFFFAOYSA-L calcium bis(dihydrogenphosphate) Chemical compound [Ca+2].OP(O)([O-])=O.OP(O)([O-])=O YYRMJZQKEFZXMX-UHFFFAOYSA-L 0.000 description 1
- 229910000389 calcium phosphate Inorganic materials 0.000 description 1
- 159000000007 calcium salts Chemical class 0.000 description 1
- 239000000378 calcium silicate Substances 0.000 description 1
- 229910052918 calcium silicate Inorganic materials 0.000 description 1
- OYACROKNLOSFPA-UHFFFAOYSA-N calcium;dioxido(oxo)silane Chemical compound [Ca+2].[O-][Si]([O-])=O OYACROKNLOSFPA-UHFFFAOYSA-N 0.000 description 1
- 125000001589 carboacyl group Chemical group 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 241001233037 catfish Species 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 239000000084 colloidal system Substances 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000005520 cutting process Methods 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 239000013530 defoamer Substances 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 239000003405 delayed action preparation Substances 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- GVGUFUZHNYFZLC-UHFFFAOYSA-N dodecyl benzenesulfonate;sodium Chemical compound [Na].CCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 GVGUFUZHNYFZLC-UHFFFAOYSA-N 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 150000002191 fatty alcohols Chemical class 0.000 description 1
- 239000003337 fertilizer Substances 0.000 description 1
- WSFSSNUMVMOOMR-UHFFFAOYSA-N formaldehyde Substances O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 1
- 238000001640 fractional crystallisation Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 235000008434 ginseng Nutrition 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
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- C07F9/6539—Five-membered rings
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Abstract
本发明涉及含有式I所示盐的杀菌组合物,特
定的新型盐,制备该化合物的方法及使用该组合物
或化合物抑制植物病菌的方法。式中n=0、1、2或
3,R代表卤原子或根据需要可被取代的烷基、卤代
烷基、烷氧基或卤代烷基,R1、R2和R3各自代表可
根据需要被取代的烷基、环烷基、苯基或苄基,而X
代表阴离子。
Description
本发明涉及含有鏻盐的杀菌组合物,特定的新型鏻盐,制备该化合物的方法以及使用这类组合物或化合物抑制植物病菌的方法。
Liebigs Ann.Chem,(1981)623-632特别披露了2-乙氧羰基噻唑-4-基甲基(三苯基)鏻溴化物和2-苯基噻唑-4-基甲基(三苯基)鏻溴化物。然而,该文献并未表明这些化合物具有杀菌活性。
业已发现,特定的噻唑-4-基鏻盐具备适用的杀菌活性,这些鏻盐中的某些属于新型化合物。因此,本发明提供了一种至少含有一种载体及通式(Ⅰ)化合物作为活性组分的杀菌组合物。
其中n=0、1、2或3;
R代表囟原子或根据需要可被取代的烷基、囟代烷基、烷氧基或囟代烷氧基;
R1、R2和R3各自代表根据需要可被取代的烷基、环烷基、苯基或苄基;
X代表阴离子。
当上述任何一种化合物含有烷基、囟代烷基、烷氧基或囟代烷氧基取代基时,则该化合物呈直链或支链状并且可含多达12个碳原子,以多达6个碳原子为佳,尤其是多达4个。
述语“囟素”和“囟”表示氟、氯、溴和碘,其中以氟、氯和溴为佳。
若任何一种上述取代基均可根据需要而被取代的话,则这类根据需要而存在的取代基可以是任意一种或多种常用于开发杀虫化合物和/或这类化合物变体的那些基团,这些基团对上述化合物的结构/活性、持久性、渗透性或其它特性具有一定的影响。这类取代基的特定实例有如囟原子、硝基、氰基、羟基、烷基、囟代烷基、烷氧基、囟代烷氧基、氨基、烷氨基、二烷基氨基、羰基、烷氧羰基、羧基、链烷酰基、烷基硫、烷基亚硫酰基、烷基磺酰基、氨基甲酰基、烷基酰氨基、环烷基和苯基。若任意一种上述取代基代表或含有一种烷基取代基时,则该取代基呈直链或支链状并含有多达12个碳原子,以多达6个,尤其是多达4个碳原子为佳。
较好地,R代表囟原子、C1-6烷基或囟代烷基、尤其是C1-4烷基或囟代烷基、或C1-6烷氧基或囟代烷氧基、特别是C1-4烷氧基或囟代烷氧基。若n=2或3,则取代基R可以相同或不同。
较好地,R1、R2和R3各自代表C1-6烷基,特别是C1-4烷基,C3-8环烷基,特别是C3-6环烷基,或根据需要可被一个或多个选自囟原子、C1-4烷基、C1-4囟代烷基、C1-4烷氧基和C1-4囟代烷氧基之类的取代基所取代的苯基,和苄基。
优选的阴离子X由强有机酸或强无机酸衍生得到,其中尤以诸如氯离子和溴离子之类的囟素阴离子为佳。
作为特别优选的式(Ⅰ)化合物,其中n=0、1或2;R代表氯原子或甲基、三氟甲基、甲氧基或三氟甲氧基;R1、R2和R3各自代表乙基、丁基、环己基、苯基、氟苯基、氯苯基、甲苯基、三氟甲苯基或甲氧苯基,苄基;X代表氯阴离子。尤其以[2-(4-氯苯基)-噻唑-4-基甲基]三苯基鏻盐为佳,其中n=1,R的4位上有取代氯原子,而R1、R2和R3各自代表未被取代的苯基。
许多式(Ⅰ)化合物都是新型化合物,所以本发明也将涉及这些新型化合物。这些新型化合物为式Ⅰ所示的磷盐,其中取代基如上所定义,跫堑盧1、R2和R3各自代表未被取代的苯基,而n=0时,则X不得为溴阴离子。
本发明还提供了制备如上定义的式(Ⅰ)化合物的方法,该方法包括使式Ⅱ化合物与式(Ⅲ)所示的膦反应。
其中n和R如上所定义,而L为可作为阴离子被分离的离去基团,
其中R1、R2和R3如上所定义。
较好地,离去基团L为氯或溴,尤以氯为佳。
反应适宜在50~150℃的温度下及诸如乙腈、丙酮、甲苯、二恶烷或四氢呋喃之类的惰性溶剂中进行。一旦被冷却,通常可使式(Ⅰ)化合物以结晶的形式被分离。
式Ⅱ化合物的制备可采用传统的方法按照下列方式进行:
式Ⅴ所式的硫代苯甲酰胺可通过式Ⅳ所示的苄腈于有机溶剂如甲苯或吡啶之中、在碱如三乙胺存在下及在理想的温度(20~50℃)条件下与硫化氢反应来制备。式Ⅳ化合物可以是已知化合物或者是采用与已知方法相类似的方法由已知化合物制备的产物。
可通过式Ⅴ所示的硫代苯甲酰胺与1,3-二氯丙酮于惰性溶剂如丙酮、二恶烷或甲苯之中、在优选温度(10~50℃)条件下进行反应来制取式Ⅵ化合物。通过空吸可分离出反应介质中的产物。
采用传统的脱水方法如用浓硫酸或多磷酸进行处理、并根据需要进行加热,便可完成式Ⅵ化合物的脱水过程,制得式Ⅱ化合物(参看A.Silberg等人,Ber.94,2887-94(1961))。
式Ⅲ所示的膦为已知化合物并且可按照由Georg Thieme Verlag,Stuttgart 1963年出版的Houben-Weyl,Vol.12/1,第17-66页的相应内容来制备。
本发明还包括一种制备上述杀菌组合物的方法,其中包括使式Ⅰ化合物与至少一种载体结合在一起。
本发明组合物中活性组分的含量以0.5~95%(重量)为佳。
本发明组合物中的载体可以是能够与活性组分配伍从而便于施用于待处理场所的任何物质,举例来说,这种材料可以是植物、种子或土壤,或者便于贮存、输送或处理的材料。载体可以是固体或液体,包括通常为气体而经压缩变为液体的物质,也可以使用任何常用于配制杀菌组合物的载体。
适用的固体载体包括天然的和合成的陶土及硅酸盐,例如天然硅石如硅藻土,硅酸镁,例如滑石;硅酸铝镁,例如绿坡缕石和蛭石;硅酸铝,例如高岭土,蒙脱土和云母;碳酸钙;硫酸钙;硫酸铵;合成水合氧化硅和合成硅酸钙或硅酸铝;单质,例如碳和硫;天然和合成树脂,例如苯并呋喃树脂、聚氯乙烯、及苯乙烯聚合物和共聚物;固体聚氯酚;沥青;蜡,例如蜂蜡,石蜡,和氯化石蜡;固体肥料,例如过磷酸钙。
适用的液体载体包括水;醇,例如异丙醇及乙二醇;酮,例如丙酮,丁酮,甲基异丁基酮和环己酮;醚;芳烃或芳脂族烃,例如苯、甲苯和二甲苯,石油馏分,例如煤油和轻质油品;氯代烃,例如四氯化碳,全氯乙烯和三氯乙烷。不同液体的混合物通常也适用。
杀菌组合物通常配制成浓缩状,并以浓缩物的形式进行输送,使用前由用户进行稀释。作为表面活性剂存在的少量载体有利于这一稀释过程的进行。在本发明组合物中,以至少有一种载体为表面活性剂为佳。例如,该组合物可含有至少两种载体,其中至少有一种为表面活性剂。
表面活性剂可以是乳化剂、分散剂或润湿剂,可以是离子的或非离子的。适用的表面活性的实例包括聚丙烯酸和木素磺酸的钠盐或钙盐,至少含12个碳原子的脂肪酸或脂族胺或酰胺与环氧乙烷和/或环氧丙烷所形成的缩合产物;丙三醇、山梨醇、蔗糖或季戊四醇的脂肪酸酯;这些化合物与环氧乙烷和/或环氧丙烷所形成的缩合物;脂肪醇或烷基酚,例如对辛基酚或对辛基甲酚,与环氧乙烷和/或环氧丙烷所形成的缩合产物;这些缩合产物的硫酸盐或磺酸盐;至少含10个碳原子的硫酸酯或磺酸酯的碱金属或碱金属盐类,其中以钠盐为佳,例如十二烷基硫酸钠,仲烷基硫酸钠、磺化蓖麻油的钠盐,以及烷芳基磺酸钠如十二烷基苯磺酸钠,环氧乙烷聚合物和环氧乙烷与环氧丙烷的共聚物。
举例来说,本发明组合物可配制为润湿粉末、粉剂、浆料、粒剂、可溶性粉末、溶液、可乳化浓缩物、乳液、悬浮液浓缩物、悬浮液及气溶胶。润湿粉末通常含25、50或75%(重量)活性组分,并且除了固体惰性载体之外通常尚含有3~10%(重量)分散剂,必要的话,还含有0~10%(重量)稳定剂和/或诸如渗透剂或粘合剂之类的其它添加剂。所配制的粉剂通常以粉尘浓缩物的形式存在,其组成与润湿粉末相似,只是不含有分散剂,于田间用另一种固体载体稀释可得到通常含0.5~10%(重量)活性组分的组合物。制成的粒剂中颗粒度通常为10~100英国标题目(1.672~0.152mm),这些颗粒可通过烧结或浸渍技术制成。粒剂中一般含有0.5~75%(重量)活性组分和0~10%(重量)诸如稳定剂、表面活性剂、缓释改进剂和粘合剂之类的添加剂。所谓“干燥可流动性粉末”由活性组分浓度较高的小颗粒组成。除了溶剂以外,必要的话,可乳化浓缩物中通常含助溶剂,1~50%(w/v)活性组分,2~20%(w/v)乳化剂及0~20%(w/v)诸如稳定剂,渗透剂和缓蚀剂之类的其它添加剂。悬浮液浓缩物通常要经过化合作用,从而产生稳定的、非沉降的可流动性产物,其中通常含10~75%(重量)活性组分,0.5~15%(重量)分散剂,0.1~10%(重量)悬浮剂如保护胶体及触变剂,0~10%(重量)其它添加剂如消泡剂、缓蚀剂、稳定剂、渗透剂和粘合剂,以及水或基本上不溶解活性组分的有机液体;上述组合物中还可溶解有特定的有机固体或无机盐以便防止沉降现象发生或是起着水防冻剂的作用。
含水分散体和乳液,例如通过用水稀释本发明润湿粉末或浓缩物而获得的组合物,也属于本发明的范畴。上述乳液可以是油包水型或水包油型,其稠度呈蛋黄酱状。
其它适用的制剂包括用聚合物包裹的水溶液或有机溶液,包裹粉末和天然与合成材料或用活性组分浸渍过的载体。
基于活性组分的离子结构,应特别注意的是制剂中的其它组分须能够与活性组分相配伍,尤其是最好也具有离子结构(例如分散剂如取代萘磺酸-甲醛缩合物,木素磺酸盐,聚丙烯酸酯,乙氧基化脂肪酸和酚的磷酸盐和硫酸盐,或润湿剂如二辛基硫代琥珀酸钠、烷基萘磺酸盐、取代和未取代的脂肪酸牛磺酰胺及季铵化合物)。以非离子助剂为佳。
配制实施例
乳液浓缩物
组合物:
本发明活性组分 200g/l
乙氧基化蓖麻油 100g/l
四氢糠醇 793g/l
密度为1.093g/ml
本发明组合物还含有其它组分,例如具备除草、杀虫或杀菌活性的其它化合物。使用载体可以使杀菌化合物向周围有待受到保护的植物中释放速度减慢,这样特别有利于延长本发明化合物的保护活性。举例来说,可将这类缓释制剂埋入靠近藤蔓植物根部的土壤中,或是在该制剂中加一种粘合剂组分以保证该制剂能够直接施用于藤蔓植物茎干部。
本发明还介绍了上述式Ⅰ化合物及其酸加成盐或金属盐铬合物作为杀菌剂的应用,并介绍了一种抑制霉菌的方法,该方法包括用该化合物处理某一场所,举例来说,这种场所可以是易遭受或受到霉菌侵害的植物,这类植物的种子或这类植物生长或有待生长的介质。
本发明可广泛地用于保护作物免受霉菌的侵害。本发明的化合物及组合物在抵御葡萄孢属、尤其是灰葡萄孢方面具有特殊的活性,并可用谒性馐芰钊松业钠咸焰呔趾Φ淖魑铩?墒艿奖;さ牡湫妥魑锇ㄆ咸选⒙砹迨怼⒉葺⒋蠖购凸凵椭参铩1;ぷ饔贸志糜敕裢ǔH【鲇谒∮玫幕衔镆约案髦滞獠恳蛩厝缙颍ǔ?赏ü∮檬视玫闹萍晾醇跚嵴庑┮蛩氐挠跋臁?
下面通过实施例对本发明作进一步描述。
实施例1
制备[2-(4-氯苯基)噻唑-4-基甲基]三苯基鏻氯化物
(a)4-氯硫代苯甲酰胺
将其68.8g(0.5mol)4-氯苄腈溶于100ml吡啶与50ml三乙胺的混合物中,在搅拌条件下,将151均匀流动的硫化氢(0.67摩尔/小时)于室温下加至该混合物中,然后于50℃下再加入111(0.5摩尔/小时),历时30分钟,总共为1.25摩尔。然后于50℃下再搅拌30分钟,并加入1.5升水。分离结晶,用大量水洗涤并干燥。产率:81g(94%理论值);熔点为129℃。
(b)4-氯硫代苯甲亚胺酸-3-氯丙酮基酯盐酸盐
将8.58g(50mmol)(a)中获得的4-氯硫代苯甲酰胺溶于35ml丙酮,并加入6.35g(50mmol)1.3-二氯丙酮,于室温下将其放置1天。分离出结晶,用丙酮洗涤并干燥。
产率:12.2g(82%理论值);熔点为149℃(分解)。
(c)4-氯甲基-2-(4-氯苯基)噻唑
将11.95g(40mmol)(b)中获得的4-氯硫代苯甲亚胺酸-3-氯丙酮基酯盐酸盐于室温下边搅拌边加至40ml浓硫酸中,于室温下放置30分钟后倾至冰上,分离出结晶,用水洗除酸后,干燥。
产率:9.6g(98%理论值);熔点:81℃。
(d)[2-(4-氯苯基)噻吩-4-基甲基]三苯基鏻氯化物
用20ml乙腈将2.44g(10mmol)于(c)中获得的4-氯甲基-2-(4-氯苯基)噻唑和2.62g(10mmol)三苯膦回流3小时,产生晶状沉淀物。冷却后,分离出结晶,经丙酮洗涤后进行干燥。
产率:3.65g(72%理论值),熔点:308~310℃。
实施例2~34
按照上述实施例1所述步骤制备本发明化合物,详见下列表1。表中化合物的种类参见式Ⅰ。
实施例35
下列试验对本发明有代表性化合物的杀菌活性进行了研究。
抵御葡萄灰霉(灰葡萄孢)的保护活性
这是一项直接保护葡萄的试验。由于灰葡萄孢通常感染具有一定含糖量的葡萄,因此应选用Ochsle度在60~90的葡萄。Ochsle度是对葡萄汁比重的度量,因而其中含糖量可由此计算。另外,重要的是须保证葡萄或茎干均未受到损坏或有任何坏死的迹象。
将选好的葡萄自距茎干5mm之处剪摘下来,然后将其浸泡在500ppm浓度的试验化合物于水、丙酮、甲醇或其混合物中所形成的溶液中,该溶剂或溶剂混合物中还含有500ppm Triton X-100。用石蜡包裹切口。另外,建立四个对照物,其中用下列物质处理葡萄:
(1)H2O-蒸馏水
(2)LA0.5=含500ppm Triton X-100的10%丙酮溶液
(3)LM0.5=含500ppm Triton X-100的10%甲醇溶液
(4)LW0.5=含500ppm Triton X-100的蒸馏水
将葡萄根据处理进行划分并于室温下分片移植于不锈钢框架上。每次处理30~50珠质地相同的葡萄。两天后,用喷雾器将每升含100000个灰葡萄孢子水悬浮液喷洒在按地块隔离处理的葡萄上。然后于20~22℃下将葡萄恒温放置于灌溉室(相对湿度为100%)内。按照感染的进程依次不断地计数受到感染的葡萄,然后计算Abbott效率如下:
效率E(%)= (BBi)/(Ki) ×100
其中AWn=第n次测定
AW1=第1次测定
BBi=在第i次测定中被感染的葡萄数目
Ki=在第i次测定中,所有(即H2O、LA、LW和LM)对照物中被感染的葡萄数目平均值。
按上述方法进行试验的结果列于下表,其中用于缩写BBx和Ex中的x为感染与测定之间的天数。
Claims (13)
2、按照权利要求1所述的组合物,其中R代表囟原子或C1-6烷基、C1-6囟代烷基、C1-6烷氧基或C1-6囟代烷氧基。
3、按照权利要求1或2所述的组合物,其中R1、R2和R3各自代表C1-6烷基或C3-8环烷基或根据需要可被一个或多个选自囟原子、C1-4烷基、C1-4囟代烷基、C1-4烷氧基和C1-4囟代烷氧基之类的取代基所取代的苯基,和苄基。
4、按照上述任何一项权利要求所述的组合物,其中X代表囟阴离子。
5、按照上述任何一项权利要求所述的组合物,其中n=0、1或2;R代表氯原子或甲基、三氟甲基,甲氧基或三氟甲氧基;R1、R2和R3各自代表乙基、丁基、环己基、苯基、氟苯基、氯苯基、甲苯基、三氟甲基苯基、苄基或甲氧苯基;X代表氯阴离子。
6、按照上述任何一项权利要求所述的组合物,其中n=1,R为取代在4位上的氯原子,而R1、R2和R3各自代表未被取代的苯基。
7、按照上述任何一项权利要求所述的组合物,其中含有至少两个载体,至少有一个为表面活性剂。
8、一种如权利要求,中式Ⅰ所示的化合物,其中n、R1、R2、R3、R和X如权利要求1所定义,条件是若R1、R2和R3各自代表未被取代的苯基而n=0的话,则X不得为溴阴离子。
9、一种制备如权利要求8所述式Ⅰ化合物的方法,其中包括使式Ⅱ化合物与式Ⅲ化合物反应
式中n和R如上所定义,L为可作为阴离子而被分离的离去基团,
式中R1、R2和R3如权利要求1所定义。
10、按照权利要求9所述的方法,其中L为氯。
11、一种抑制霉菌的方法,其中包括用杀菌有效量的如权利要求1~7中任何一项所述组合物或如权利要求8所述化合物处理场所。
12、按照权利要求11所述的方法,其中场所包括易遭受或受到霉菌侵害的植物,这类植物的种子或这类植物正在生长或有待生长的介质。
13、应用如权利要求1~6和8中任何一项所定义的式Ⅰ化合物作为杀菌剂。
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE37239193.9 | 1987-07-18 | ||
DE19873723913 DE3723913A1 (de) | 1987-07-18 | 1987-07-18 | Neue phosphoniumsalze, ihre herstellung und verwendung |
Publications (2)
Publication Number | Publication Date |
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CN1032794A true CN1032794A (zh) | 1989-05-10 |
CN1020392C CN1020392C (zh) | 1993-05-05 |
Family
ID=6331930
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Application Number | Title | Priority Date | Filing Date |
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CN88104364A Expired - Fee Related CN1020392C (zh) | 1987-07-18 | 1988-07-15 | 盐杀菌组合物及其应用 |
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Country | Link |
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US (1) | US4933328A (zh) |
EP (1) | EP0300574B1 (zh) |
JP (1) | JPH0193596A (zh) |
CN (1) | CN1020392C (zh) |
AT (1) | ATE101157T1 (zh) |
DE (2) | DE3723913A1 (zh) |
MX (1) | MX172679B (zh) |
NZ (1) | NZ225429A (zh) |
PH (1) | PH26189A (zh) |
PT (1) | PT88005B (zh) |
ZA (1) | ZA885127B (zh) |
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NZ237758A (en) * | 1990-04-17 | 1992-12-23 | Shell Int Research | (phenylalkyl) triphenylphosphonium salt derivatives and fungicidal compositions |
US5273986A (en) * | 1992-07-02 | 1993-12-28 | Hoffmann-La Roche Inc. | Cycloalkylthiazoles |
DE69413790T2 (de) | 1993-07-14 | 1999-02-25 | Nippon Chemical Industrial Co., Ltd., Tokio/Tokyo | Antibakterielles polymer, kontaktlinse und kontaktlinsenpflegeprodukt |
JP4716547B2 (ja) * | 2000-08-10 | 2011-07-06 | 住友精化株式会社 | 2−フェニルチアゾール類の製造方法 |
US8936728B2 (en) | 2010-08-31 | 2015-01-20 | Debra A. Riggs | Chemicals for oil spill cleanup |
JP6327841B2 (ja) * | 2013-12-06 | 2018-05-23 | 住友精化株式会社 | 芳香族チアゾール化合物の製造方法 |
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US3159645A (en) * | 1960-12-29 | 1964-12-01 | Dow Chemical Co | Omcrion-thiazolyl omcrion-alkyl phosphoramido-thioates |
US3652735A (en) * | 1969-05-01 | 1972-03-28 | Carlisle Chemical Works | Quaternary phosphonium dialkyl phosphates |
-
1987
- 1987-07-18 DE DE19873723913 patent/DE3723913A1/de not_active Withdrawn
-
1988
- 1988-07-14 DE DE3887582T patent/DE3887582T2/de not_active Expired - Fee Related
- 1988-07-14 PH PH37229A patent/PH26189A/en unknown
- 1988-07-14 EP EP88201520A patent/EP0300574B1/en not_active Expired - Lifetime
- 1988-07-14 AT AT88201520T patent/ATE101157T1/de not_active IP Right Cessation
- 1988-07-15 MX MX012297A patent/MX172679B/es unknown
- 1988-07-15 NZ NZ225429A patent/NZ225429A/en unknown
- 1988-07-15 CN CN88104364A patent/CN1020392C/zh not_active Expired - Fee Related
- 1988-07-15 JP JP63175278A patent/JPH0193596A/ja active Pending
- 1988-07-15 PT PT88005A patent/PT88005B/pt not_active IP Right Cessation
- 1988-07-15 ZA ZA885127A patent/ZA885127B/xx unknown
- 1988-07-18 US US07/220,736 patent/US4933328A/en not_active Expired - Fee Related
Also Published As
Publication number | Publication date |
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PT88005B (pt) | 1995-03-01 |
ATE101157T1 (de) | 1994-02-15 |
JPH0193596A (ja) | 1989-04-12 |
PH26189A (en) | 1992-03-18 |
PT88005A (pt) | 1989-06-30 |
DE3887582T2 (de) | 1994-05-19 |
NZ225429A (en) | 1990-12-21 |
CN1020392C (zh) | 1993-05-05 |
US4933328A (en) | 1990-06-12 |
MX172679B (es) | 1994-01-07 |
EP0300574A3 (en) | 1990-04-25 |
ZA885127B (en) | 1989-04-26 |
EP0300574B1 (en) | 1994-02-02 |
DE3887582D1 (de) | 1994-03-17 |
DE3723913A1 (de) | 1989-02-23 |
EP0300574A2 (en) | 1989-01-25 |
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