HU185878B - Fungicide compositions and process for producing pyridyl-imino-methyl-aenzene derivatives as active agents - Google Patents
Fungicide compositions and process for producing pyridyl-imino-methyl-aenzene derivatives as active agents Download PDFInfo
- Publication number
- HU185878B HU185878B HU80570A HU57080A HU185878B HU 185878 B HU185878 B HU 185878B HU 80570 A HU80570 A HU 80570A HU 57080 A HU57080 A HU 57080A HU 185878 B HU185878 B HU 185878B
- Authority
- HU
- Hungary
- Prior art keywords
- formula
- alkoxy
- alkyl
- found
- cyano
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 50
- 230000000855 fungicidal effect Effects 0.000 title claims abstract description 21
- 238000000034 method Methods 0.000 title claims abstract description 14
- 230000008569 process Effects 0.000 title claims description 9
- 239000000417 fungicide Substances 0.000 title description 6
- 239000013543 active substance Substances 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 52
- -1 cyano, ethynyl Chemical group 0.000 claims abstract description 19
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 12
- 125000005843 halogen group Chemical group 0.000 claims abstract description 10
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 8
- 239000001257 hydrogen Substances 0.000 claims abstract description 7
- 125000004414 alkyl thio group Chemical class 0.000 claims abstract description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 4
- 239000004094 surface-active agent Substances 0.000 claims description 26
- 239000004480 active ingredient Substances 0.000 claims description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 17
- 239000007787 solid Substances 0.000 claims description 14
- 238000002360 preparation method Methods 0.000 claims description 11
- 229910052736 halogen Inorganic materials 0.000 claims description 9
- 239000002253 acid Substances 0.000 claims description 8
- 150000002367 halogens Chemical class 0.000 claims description 6
- 239000007788 liquid Substances 0.000 claims description 6
- 239000002270 dispersing agent Substances 0.000 claims description 5
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 239000000969 carrier Substances 0.000 claims description 4
- 239000003995 emulsifying agent Substances 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- 229910052783 alkali metal Chemical group 0.000 claims description 3
- 150000001340 alkali metals Chemical group 0.000 claims description 3
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 3
- 239000002480 mineral oil Substances 0.000 claims description 3
- 239000002516 radical scavenger Substances 0.000 claims description 3
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims 1
- 125000002947 alkylene group Chemical group 0.000 claims 1
- 125000000129 anionic group Chemical group 0.000 claims 1
- 125000002091 cationic group Chemical group 0.000 claims 1
- 239000002734 clay mineral Substances 0.000 claims 1
- 239000003960 organic solvent Substances 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 abstract description 10
- 150000003839 salts Chemical class 0.000 abstract description 7
- 229910052757 nitrogen Inorganic materials 0.000 abstract description 4
- 229910052760 oxygen Inorganic materials 0.000 abstract description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 abstract description 2
- 125000001188 haloalkyl group Chemical group 0.000 abstract description 2
- 239000000543 intermediate Substances 0.000 abstract description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract description 2
- 125000004996 haloaryloxy group Chemical group 0.000 abstract 2
- 125000006413 ring segment Chemical group 0.000 abstract 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- 239000005864 Sulphur Chemical group 0.000 abstract 1
- 125000003302 alkenyloxy group Chemical group 0.000 abstract 1
- 125000005108 alkenylthio group Chemical class 0.000 abstract 1
- 125000005133 alkynyloxy group Chemical group 0.000 abstract 1
- 125000005109 alkynylthio group Chemical class 0.000 abstract 1
- 125000004659 aryl alkyl thio group Chemical group 0.000 abstract 1
- 125000002102 aryl alkyloxo group Chemical group 0.000 abstract 1
- 125000005110 aryl thio group Chemical class 0.000 abstract 1
- 125000004104 aryloxy group Chemical group 0.000 abstract 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- 125000005366 cycloalkylthio group Chemical class 0.000 abstract 1
- 125000004438 haloalkoxy group Chemical group 0.000 abstract 1
- 125000005842 heteroatom Chemical group 0.000 abstract 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- 150000002431 hydrogen Chemical group 0.000 abstract 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 abstract 1
- 239000001301 oxygen Chemical group 0.000 abstract 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 30
- 239000003921 oil Substances 0.000 description 30
- 241000196324 Embryophyta Species 0.000 description 24
- 125000001309 chloro group Chemical group Cl* 0.000 description 24
- 230000000694 effects Effects 0.000 description 14
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 12
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- 230000015572 biosynthetic process Effects 0.000 description 9
- 239000000460 chlorine Substances 0.000 description 9
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 9
- 239000007921 spray Substances 0.000 description 9
- 238000011156 evaluation Methods 0.000 description 8
- 239000000843 powder Substances 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 5
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 5
- 240000005979 Hordeum vulgare Species 0.000 description 5
- 235000007340 Hordeum vulgare Nutrition 0.000 description 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 5
- 239000007900 aqueous suspension Substances 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- YTOPFCCWCSOHFV-UHFFFAOYSA-N 2,6-dimethyl-4-tridecylmorpholine Chemical compound CCCCCCCCCCCCCN1CC(C)OC(C)C1 YTOPFCCWCSOHFV-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical class Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 4
- 239000000654 additive Substances 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
- 239000011575 calcium Substances 0.000 description 4
- 239000007859 condensation product Substances 0.000 description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
- 239000004495 emulsifiable concentrate Substances 0.000 description 4
- 239000000839 emulsion Substances 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 159000000000 sodium salts Chemical class 0.000 description 4
- 238000005507 spraying Methods 0.000 description 4
- 239000003381 stabilizer Substances 0.000 description 4
- 239000004546 suspension concentrate Substances 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- 244000105624 Arachis hypogaea Species 0.000 description 3
- 241001480061 Blumeria graminis Species 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 241000221785 Erysiphales Species 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- 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 3
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 240000006365 Vitis vinifera Species 0.000 description 3
- 235000014787 Vitis vinifera Nutrition 0.000 description 3
- 230000002528 anti-freeze Effects 0.000 description 3
- 239000000022 bacteriostatic agent Substances 0.000 description 3
- RIOXQFHNBCKOKP-UHFFFAOYSA-N benomyl Chemical compound C1=CC=C2N(C(=O)NCCCC)C(NC(=O)OC)=NC2=C1 RIOXQFHNBCKOKP-UHFFFAOYSA-N 0.000 description 3
- TXPVUYLRHHHRLY-UHFFFAOYSA-N benzenecarboximidoyl chloride;hydrochloride Chemical compound Cl.ClC(=N)C1=CC=CC=C1 TXPVUYLRHHHRLY-UHFFFAOYSA-N 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 239000012141 concentrate Substances 0.000 description 3
- 235000008504 concentrate Nutrition 0.000 description 3
- 239000008187 granular material Substances 0.000 description 3
- 230000001681 protective effect Effects 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000004550 soluble concentrate Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 229910052717 sulfur Inorganic materials 0.000 description 3
- 239000000375 suspending agent Substances 0.000 description 3
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 description 2
- CUYKNJBYIJFRCU-UHFFFAOYSA-N 3-aminopyridine Chemical compound NC1=CC=CN=C1 CUYKNJBYIJFRCU-UHFFFAOYSA-N 0.000 description 2
- 235000017060 Arachis glabrata Nutrition 0.000 description 2
- 235000010777 Arachis hypogaea Nutrition 0.000 description 2
- 235000018262 Arachis monticola Nutrition 0.000 description 2
- 241000123650 Botrytis cinerea Species 0.000 description 2
- 239000005742 Bupirimate Substances 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- 241000221787 Erysiphe Species 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- 241000233866 Fungi Species 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 241000315044 Passalora arachidicola Species 0.000 description 2
- 229920001213 Polysorbate 20 Polymers 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 244000061456 Solanum tuberosum Species 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- 235000009754 Vitis X bourquina Nutrition 0.000 description 2
- 235000012333 Vitis X labruscana Nutrition 0.000 description 2
- 125000002877 alkyl aryl group Chemical group 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- 235000012211 aluminium silicate Nutrition 0.000 description 2
- 230000000845 anti-microbial effect Effects 0.000 description 2
- 238000003556 assay Methods 0.000 description 2
- MITFXPHMIHQXPI-UHFFFAOYSA-N benzoxaprofen Natural products N=1C2=CC(C(C(O)=O)C)=CC=C2OC=1C1=CC=C(Cl)C=C1 MITFXPHMIHQXPI-UHFFFAOYSA-N 0.000 description 2
- DSKJPMWIHSOYEA-UHFFFAOYSA-N bupirimate Chemical compound CCCCC1=C(C)N=C(NCC)N=C1OS(=O)(=O)N(C)C DSKJPMWIHSOYEA-UHFFFAOYSA-N 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
- 230000000052 comparative effect Effects 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 230000007797 corrosion Effects 0.000 description 2
- 238000005260 corrosion Methods 0.000 description 2
- 125000002933 cyclohexyloxy group Chemical group C1(CCCCC1)O* 0.000 description 2
- JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 150000004665 fatty acids Chemical class 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 235000011167 hydrochloric acid Nutrition 0.000 description 2
- 208000015181 infectious disease Diseases 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 2
- 230000002147 killing effect Effects 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 235000020232 peanut Nutrition 0.000 description 2
- 239000008389 polyethoxylated castor oil Substances 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 description 2
- 235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 description 2
- KJRCEJOSASVSRA-UHFFFAOYSA-N propane-2-thiol Chemical compound CC(C)S KJRCEJOSASVSRA-UHFFFAOYSA-N 0.000 description 2
- 125000005930 sec-butyloxycarbonyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(OC(*)=O)C([H])([H])[H] 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- GPRLSGONYQIRFK-MNYXATJNSA-N triton Chemical compound [3H+] GPRLSGONYQIRFK-MNYXATJNSA-N 0.000 description 2
- 239000004563 wettable powder Substances 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- 125000004178 (C1-C4) alkyl 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
- DGXRGGUNBXNJRI-UHFFFAOYSA-N 2-methyl-4-octylphenol Chemical compound CCCCCCCCC1=CC=C(O)C(C)=C1 DGXRGGUNBXNJRI-UHFFFAOYSA-N 0.000 description 1
- YEVROGRCGBMUHC-UHFFFAOYSA-N 2-methylpropyl benzenecarboximidothioate Chemical compound N=C(SCC(C)C)C1=CC=CC=C1 YEVROGRCGBMUHC-UHFFFAOYSA-N 0.000 description 1
- NTDQQZYCCIDJRK-UHFFFAOYSA-N 4-octylphenol Chemical compound CCCCCCCCC1=CC=C(O)C=C1 NTDQQZYCCIDJRK-UHFFFAOYSA-N 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- YRLYOMQUYNMAMK-UHFFFAOYSA-N C1=CC=CC(=C1)C(=N)SC(C)C Chemical compound C1=CC=CC(=C1)C(=N)SC(C)C YRLYOMQUYNMAMK-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 206010017533 Fungal infection Diseases 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- 208000031888 Mycoses Diseases 0.000 description 1
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 description 1
- 241000283973 Oryctolagus cuniculus Species 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical group ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 description 1
- 241000233622 Phytophthora infestans Species 0.000 description 1
- 241001123569 Puccinia recondita Species 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
- 235000002595 Solanum tuberosum Nutrition 0.000 description 1
- 235000021307 Triticum Nutrition 0.000 description 1
- 244000098338 Triticum aestivum Species 0.000 description 1
- 241000221577 Uromyces appendiculatus Species 0.000 description 1
- 208000027418 Wounds and injury Diseases 0.000 description 1
- 241000607479 Yersinia pestis Species 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 238000005054 agglomeration Methods 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 230000004075 alteration Effects 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 230000003373 anti-fouling effect Effects 0.000 description 1
- 239000002518 antifoaming agent Substances 0.000 description 1
- 239000007798 antifreeze agent Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000010426 asphalt Substances 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
- 235000013871 bee wax Nutrition 0.000 description 1
- 239000012166 beeswax Substances 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 159000000007 calcium salts Chemical class 0.000 description 1
- YYRMJZQKEFZXMX-UHFFFAOYSA-N calcium;phosphoric acid Chemical compound [Ca+2].OP(O)(O)=O.OP(O)(O)=O YYRMJZQKEFZXMX-UHFFFAOYSA-N 0.000 description 1
- JHRWWRDRBPCWTF-OLQVQODUSA-N captafol Chemical compound C1C=CC[C@H]2C(=O)N(SC(Cl)(Cl)C(Cl)Cl)C(=O)[C@H]21 JHRWWRDRBPCWTF-OLQVQODUSA-N 0.000 description 1
- 239000004359 castor oil Substances 0.000 description 1
- 235000019438 castor oil Nutrition 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 239000000084 colloidal system Substances 0.000 description 1
- 239000002361 compost Substances 0.000 description 1
- 238000007906 compression Methods 0.000 description 1
- 230000006835 compression Effects 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 125000003963 dichloro group Chemical group Cl* 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 238000003113 dilution method Methods 0.000 description 1
- 235000019329 dioctyl sodium sulphosuccinate Nutrition 0.000 description 1
- YHAIUSTWZPMYGG-UHFFFAOYSA-L disodium;2,2-dioctyl-3-sulfobutanedioate Chemical compound [Na+].[Na+].CCCCCCCCC(C([O-])=O)(C(C([O-])=O)S(O)(=O)=O)CCCCCCCC YHAIUSTWZPMYGG-UHFFFAOYSA-L 0.000 description 1
- 238000004821 distillation 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
- 238000001035 drying Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 150000002191 fatty alcohols Chemical class 0.000 description 1
- 239000003337 fertilizer Substances 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 230000002538 fungal effect Effects 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 150000004676 glycans Chemical class 0.000 description 1
- 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 1
- 150000002334 glycols Chemical class 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 238000005470 impregnation Methods 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 208000014674 injury Diseases 0.000 description 1
- 238000011081 inoculation Methods 0.000 description 1
- 239000002054 inoculum Substances 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 239000003350 kerosene Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000012263 liquid product Substances 0.000 description 1
- HCWCAKKEBCNQJP-UHFFFAOYSA-N magnesium orthosilicate Chemical compound [Mg+2].[Mg+2].[O-][Si]([O-])([O-])[O-] HCWCAKKEBCNQJP-UHFFFAOYSA-N 0.000 description 1
- 239000000391 magnesium silicate Substances 0.000 description 1
- 229910052919 magnesium silicate Inorganic materials 0.000 description 1
- 235000019792 magnesium silicate Nutrition 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000010445 mica Substances 0.000 description 1
- 229910052618 mica group Inorganic materials 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 239000012184 mineral wax Substances 0.000 description 1
- 125000002757 morpholinyl group Chemical group 0.000 description 1
- 208000013435 necrotic lesion Diseases 0.000 description 1
- 231100001184 nonphytotoxic Toxicity 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 230000037361 pathway Effects 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 125000004193 piperazinyl group Chemical group 0.000 description 1
- 125000003386 piperidinyl group Chemical group 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 230000010152 pollination Effects 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 229920001282 polysaccharide Polymers 0.000 description 1
- 239000005017 polysaccharide Substances 0.000 description 1
- 229920000136 polysorbate Polymers 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 235000014483 powder concentrate Nutrition 0.000 description 1
- 239000011814 protection agent Substances 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
- 229940081974 saccharin Drugs 0.000 description 1
- 235000019204 saccharin Nutrition 0.000 description 1
- 239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- LIVNPJMFVYWSIS-UHFFFAOYSA-N silicon monoxide Chemical class [Si-]#[O+] LIVNPJMFVYWSIS-UHFFFAOYSA-N 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 229940080264 sodium dodecylbenzenesulfonate Drugs 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000004834 spray adhesive Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 150000003459 sulfonic acid esters Chemical class 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000002426 superphosphate Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 229950011008 tetrachloroethylene Drugs 0.000 description 1
- 125000004568 thiomorpholinyl group Chemical group 0.000 description 1
- 235000019354 vermiculite Nutrition 0.000 description 1
- 230000009278 visceral effect Effects 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 238000001238 wet grinding Methods 0.000 description 1
- 239000000080 wetting agent Substances 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
- C07D213/72—Nitrogen atoms
- C07D213/74—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Agronomy & Crop Science (AREA)
- General Health & Medical Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Pyridine Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
- Indole Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB7908822 | 1979-03-13 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HU185878B true HU185878B (en) | 1985-04-28 |
Family
ID=10503839
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU80570A HU185878B (en) | 1979-03-13 | 1980-03-11 | Fungicide compositions and process for producing pyridyl-imino-methyl-aenzene derivatives as active agents |
Country Status (24)
| Country | Link |
|---|---|
| EP (1) | EP0015628B1 (enExample) |
| JP (1) | JPS55124764A (enExample) |
| AT (1) | ATE11483T1 (enExample) |
| AU (1) | AU533020B2 (enExample) |
| BG (2) | BG31498A3 (enExample) |
| BR (1) | BR8001433A (enExample) |
| CA (1) | CA1160229A (enExample) |
| DD (2) | DD149452A5 (enExample) |
| DE (1) | DE3070045D1 (enExample) |
| DK (1) | DK159423C (enExample) |
| EG (1) | EG14257A (enExample) |
| ES (1) | ES8104231A1 (enExample) |
| HU (1) | HU185878B (enExample) |
| IE (1) | IE49554B1 (enExample) |
| IL (1) | IL59586A (enExample) |
| IN (1) | IN153816B (enExample) |
| MX (1) | MX5868E (enExample) |
| NZ (1) | NZ193094A (enExample) |
| OA (1) | OA06485A (enExample) |
| PH (1) | PH17400A (enExample) |
| PL (1) | PL121497B1 (enExample) |
| SU (1) | SU1281153A3 (enExample) |
| TR (1) | TR21441A (enExample) |
| ZA (1) | ZA801413B (enExample) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4831044A (en) * | 1987-10-29 | 1989-05-16 | Ici Americas Inc. | Fungicidal pyridyl cyclopropane carboxamidines |
| US4994473A (en) * | 1987-11-17 | 1991-02-19 | Ici Americas Inc. | Pyridyl containing insecticides |
| GB8922691D0 (en) * | 1989-10-09 | 1989-11-22 | Ici Plc | Fungicides |
| EP0422848A1 (en) * | 1989-10-09 | 1991-04-17 | Imperial Chemical Industries Plc | Fungicides |
| US5364943A (en) * | 1991-11-27 | 1994-11-15 | Pfizer Inc. | Preparation of substituted piperidines |
| JPH0794439B2 (ja) * | 1990-05-31 | 1995-10-11 | フアイザー・インコーポレイテツド | 置換ピペリジンの製造法 |
| GB9024873D0 (en) * | 1990-11-15 | 1991-01-02 | Ici Plc | Fungicidal compounds |
| ATE209186T1 (de) * | 1992-05-18 | 2001-12-15 | Pfizer | Überbrückte azabicyclische derivate als substanz p antagonisten |
| CA2141051A1 (en) * | 1992-08-04 | 1994-02-17 | Terry J. Rosen | Substituted nitrogen-containing heterocycles |
| US8513286B2 (en) * | 2007-02-22 | 2013-08-20 | Syngenta Crop Protection Llc | Iminipyridine derivatives and their uses as microbiocides |
| EP2264012A1 (de) * | 2009-06-03 | 2010-12-22 | Bayer CropScience AG | Heteroarylamidine und deren Verwendung als Fungizide |
| EP2264011A1 (de) * | 2009-06-03 | 2010-12-22 | Bayer CropScience AG | Heteroarylamidine und deren Verwendung als Fungizide |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2472292A (en) * | 1945-07-27 | 1949-06-07 | Pyridium Corp | Benzylideneamino compounds of pyridine |
| NL100994C (enExample) * | 1956-07-04 | |||
| FR1437425A (fr) * | 1964-12-29 | 1966-05-06 | Pechiney Progil Sa | Nouveaux produits fongicides à usage agricole dérivés de l'aldéhyde salicylique |
| US3472743A (en) * | 1966-12-19 | 1969-10-14 | Du Pont | Zinc plating baths and additives therefor |
| ZA775350B (en) * | 1976-12-23 | 1978-07-26 | Ciba Geigy Ag | Substituted 5-amino-2-pyridinecarboxylic acids |
| EP0000816A1 (en) * | 1977-08-06 | 1979-02-21 | Beecham Group Plc | Substituted amino-pyridine derivatives, processes for their preparation and pharmaceutical compositions containing them |
-
1980
- 1980-02-08 CA CA000345301A patent/CA1160229A/en not_active Expired
- 1980-02-26 PH PH23692A patent/PH17400A/en unknown
- 1980-03-06 EP EP80200212A patent/EP0015628B1/en not_active Expired
- 1980-03-06 DE DE8080200212T patent/DE3070045D1/de not_active Expired
- 1980-03-06 AT AT80200212T patent/ATE11483T1/de not_active IP Right Cessation
- 1980-03-11 TR TR21441A patent/TR21441A/xx unknown
- 1980-03-11 PL PL1980222598A patent/PL121497B1/pl unknown
- 1980-03-11 NZ NZ193094A patent/NZ193094A/xx unknown
- 1980-03-11 EG EG142/80A patent/EG14257A/xx active
- 1980-03-11 DD DD80219586A patent/DD149452A5/de not_active IP Right Cessation
- 1980-03-11 JP JP2985580A patent/JPS55124764A/ja active Granted
- 1980-03-11 AU AU56347/80A patent/AU533020B2/en not_active Ceased
- 1980-03-11 ZA ZA00801413A patent/ZA801413B/xx unknown
- 1980-03-11 BG BG049336A patent/BG31498A3/xx unknown
- 1980-03-11 BG BG046940A patent/BG31473A3/xx unknown
- 1980-03-11 HU HU80570A patent/HU185878B/hu not_active IP Right Cessation
- 1980-03-11 IL IL59586A patent/IL59586A/xx not_active IP Right Cessation
- 1980-03-11 BR BR8001433A patent/BR8001433A/pt not_active IP Right Cessation
- 1980-03-11 DK DK104980A patent/DK159423C/da not_active IP Right Cessation
- 1980-03-11 OA OA57050A patent/OA06485A/xx unknown
- 1980-03-11 DD DD80227941A patent/DD156563A5/de unknown
- 1980-03-11 MX MX808703U patent/MX5868E/es unknown
- 1980-03-11 SU SU802891905A patent/SU1281153A3/ru active
- 1980-03-11 IN IN176/DEL/80A patent/IN153816B/en unknown
- 1980-03-11 IE IE496/80A patent/IE49554B1/en not_active IP Right Cessation
- 1980-03-11 ES ES489421A patent/ES8104231A1/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| SU1281153A3 (ru) | 1986-12-30 |
| EP0015628A1 (en) | 1980-09-17 |
| IL59586A0 (en) | 1980-06-30 |
| ES489421A0 (es) | 1981-04-01 |
| DK104980A (da) | 1980-09-14 |
| BR8001433A (pt) | 1980-11-11 |
| IE800496L (en) | 1980-09-13 |
| IL59586A (en) | 1984-05-31 |
| BG31473A3 (en) | 1982-01-15 |
| AU533020B2 (en) | 1983-10-27 |
| AU5634780A (en) | 1980-09-18 |
| OA06485A (fr) | 1981-07-31 |
| ATE11483T1 (de) | 1985-02-15 |
| DD149452A5 (de) | 1981-07-15 |
| DK159423C (da) | 1991-03-18 |
| MX5868E (es) | 1984-08-15 |
| ZA801413B (en) | 1981-03-25 |
| EG14257A (en) | 1983-09-30 |
| PH17400A (en) | 1984-08-08 |
| IN153816B (enExample) | 1984-08-18 |
| NZ193094A (en) | 1982-08-17 |
| DK159423B (da) | 1990-10-15 |
| EP0015628B1 (en) | 1985-01-30 |
| PL222598A1 (enExample) | 1980-12-15 |
| CA1160229A (en) | 1984-01-10 |
| IE49554B1 (en) | 1985-10-30 |
| DD156563A5 (de) | 1982-09-08 |
| ES8104231A1 (es) | 1981-04-01 |
| JPS6348866B2 (enExample) | 1988-09-30 |
| PL121497B1 (en) | 1982-05-31 |
| TR21441A (tr) | 1984-06-04 |
| BG31498A3 (en) | 1982-01-15 |
| DE3070045D1 (en) | 1985-03-14 |
| JPS55124764A (en) | 1980-09-26 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| HU219977B (hu) | Fungicid hatású dihalogén-triazolo-pirimidin-származékok, eljárás előállításukra, valamint a vegyületeket tartalmazó fungicid készítmények és gombairtási eljárás | |
| EP0296673B1 (en) | Thiazole derivatives | |
| PL147685B1 (en) | Insecticide | |
| HU194481B (en) | Fungicide composition containing ethane derivatives and process for producing the active agents | |
| PL87259B1 (enExample) | ||
| DD149452A5 (de) | Fungizide zusammensetzung | |
| JPS63145277A (ja) | カルバモイルイミダゾール誘導体、それらの製造方法およびそれらの殺菌剤としての用途 | |
| HU208318B (en) | Process for producing thiazole derivatives, fungicidal composition comprising thiazole derivative as active ingredient and its application | |
| CA1274524A (en) | Imidazole derivatives, their preparation and their use as fungicides | |
| CS270213B2 (en) | Fungicide and method of its active substance production | |
| HU200894B (en) | Fungicixe compositions containing benzothiazinone derivatives as active components and process for producing these compounds | |
| AU605774B2 (en) | Imidazole derivatives, their preparation and their use as fungicides | |
| PL87004B1 (enExample) | ||
| EP0152131B1 (en) | Carboxamide derivatives, their preparation and their use as fungicides | |
| HU200890B (en) | Fungicide compositions containing naphtimidazol derivatives as active components and process for producing these compounds | |
| CN87106446A (zh) | 杀菌剂组合物 | |
| JPS6333368A (ja) | イミダゾ−ル誘導体 | |
| HU193707B (en) | Fungicide and bactericide compositions, and process for the preparation of iodoacetamide derivatives used as active ingredient | |
| JPS59199667A (ja) | Ｎ−スルフエニル化フエネチルスルホンアミド及びその製造法 | |
| JPH01157965A (ja) | 殺菌性ピリジルカルバメート及びそれらの塩 | |
| CN1361663A (zh) | 杀真菌活性化合物组合物 | |
| JP2001220302A (ja) | シロアリ抑制法 | |
| US3224932A (en) | Bis(diisopropylthiocarbamoyl)sulfide as a fungicide | |
| JP3368093B2 (ja) | トリフェニルボラン誘導体及び工業用防腐防黴剤 | |
| DE3332716A1 (de) | Neue quartaere phosphoniumsalze und deren verwendung als mikrobizide mittel |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| HU90 | Patent valid on 900628 | ||
| HMM4 | Cancellation of final prot. due to non-payment of fee |