DD149452A5 - Fungizide zusammensetzung - Google Patents
Fungizide zusammensetzung Download PDFInfo
- Publication number
- DD149452A5 DD149452A5 DD80219586A DD21958680A DD149452A5 DD 149452 A5 DD149452 A5 DD 149452A5 DD 80219586 A DD80219586 A DD 80219586A DD 21958680 A DD21958680 A DD 21958680A DD 149452 A5 DD149452 A5 DD 149452A5
- Authority
- DD
- German Democratic Republic
- Prior art keywords
- formula
- compound
- hydrogen
- alkyl
- alkoxy
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 41
- 230000000855 fungicidal effect Effects 0.000 title claims abstract description 21
- 150000001875 compounds Chemical class 0.000 claims abstract description 61
- -1 cyano, ethynyl Chemical group 0.000 claims abstract description 21
- 239000001257 hydrogen Substances 0.000 claims abstract description 19
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 19
- 150000003839 salts Chemical class 0.000 claims abstract description 14
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 13
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 12
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 12
- 238000000034 method Methods 0.000 claims abstract description 10
- 125000004414 alkyl thio group Chemical class 0.000 claims abstract description 9
- 125000004104 aryloxy group Chemical group 0.000 claims abstract description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 7
- 125000006413 ring segment Chemical group 0.000 claims abstract description 7
- 125000004996 haloaryloxy group Chemical group 0.000 claims abstract description 6
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 5
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 4
- 125000005108 alkenylthio group Chemical class 0.000 claims abstract description 4
- 125000005109 alkynylthio group Chemical class 0.000 claims abstract description 4
- 125000005110 aryl thio group Chemical class 0.000 claims abstract description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 4
- 125000005366 cycloalkylthio group Chemical class 0.000 claims abstract description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 4
- 125000003302 alkenyloxy group Chemical group 0.000 claims abstract description 3
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract description 3
- 125000005133 alkynyloxy group Chemical group 0.000 claims abstract description 3
- 125000004659 aryl alkyl thio group Chemical group 0.000 claims abstract description 3
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims abstract description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 3
- 125000004438 haloalkoxy group Chemical group 0.000 claims abstract description 3
- 125000001188 haloalkyl group Chemical group 0.000 claims abstract description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 3
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 3
- 239000001301 oxygen Chemical group 0.000 claims abstract description 3
- 150000002431 hydrogen Chemical group 0.000 claims abstract 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 18
- 239000004480 active ingredient Substances 0.000 claims description 17
- 239000002253 acid Substances 0.000 claims description 13
- 229910052736 halogen Inorganic materials 0.000 claims description 10
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 9
- 150000002367 halogens Chemical group 0.000 claims description 8
- 230000002538 fungal effect Effects 0.000 claims description 7
- 125000001424 substituent group Chemical group 0.000 claims description 7
- CUYKNJBYIJFRCU-UHFFFAOYSA-N 3-aminopyridine Chemical compound NC1=CC=CN=C1 CUYKNJBYIJFRCU-UHFFFAOYSA-N 0.000 claims description 6
- 239000000460 chlorine Substances 0.000 claims description 5
- 229910052801 chlorine Inorganic materials 0.000 claims description 5
- 125000003282 alkyl amino group Chemical group 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 3
- 239000002689 soil Substances 0.000 claims description 3
- 125000005415 substituted alkoxy group Chemical group 0.000 claims description 3
- 229910052783 alkali metal Chemical group 0.000 claims description 2
- 150000001340 alkali metals Chemical group 0.000 claims description 2
- 125000005122 aminoalkylamino group Chemical group 0.000 claims description 2
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- 125000000027 (C1-C10) alkoxy group Chemical group 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 abstract description 8
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 abstract description 4
- 125000000753 cycloalkyl group Chemical group 0.000 abstract description 2
- 125000005842 heteroatom Chemical group 0.000 abstract description 2
- 239000000543 intermediate Substances 0.000 abstract description 2
- 239000005864 Sulphur Chemical group 0.000 abstract 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 29
- 238000012360 testing method Methods 0.000 description 26
- 241000196324 Embryophyta Species 0.000 description 20
- 239000003921 oil Substances 0.000 description 16
- 201000010099 disease Diseases 0.000 description 15
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 15
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- 239000007787 solid Substances 0.000 description 9
- 239000000243 solution Substances 0.000 description 8
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 8
- 238000004458 analytical method Methods 0.000 description 7
- 239000007921 spray Substances 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 239000004094 surface-active agent Substances 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 5
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 5
- 239000007900 aqueous suspension Substances 0.000 description 5
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 238000005507 spraying Methods 0.000 description 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 239000000654 additive Substances 0.000 description 4
- 239000002270 dispersing agent Substances 0.000 description 4
- 239000000417 fungicide Substances 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000000741 silica gel Substances 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- 239000003381 stabilizer Substances 0.000 description 4
- 239000012258 stirred mixture Substances 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- 241000233866 Fungi Species 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- 240000005979 Hordeum vulgare Species 0.000 description 3
- 235000007340 Hordeum vulgare Nutrition 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- 240000006365 Vitis vinifera Species 0.000 description 3
- 235000014787 Vitis vinifera Nutrition 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 239000011575 calcium Substances 0.000 description 3
- 239000000969 carrier Substances 0.000 description 3
- 239000007859 condensation product Substances 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
- 239000008187 granular material Substances 0.000 description 3
- 238000011081 inoculation Methods 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 150000004760 silicates Chemical class 0.000 description 3
- 230000028070 sporulation Effects 0.000 description 3
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 description 2
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-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
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 239000000853 adhesive Substances 0.000 description 2
- 230000001070 adhesive effect Effects 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 125000003342 alkenyl group Chemical group 0.000 description 2
- 125000000304 alkynyl group Chemical group 0.000 description 2
- 230000015572 biosynthetic process Effects 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
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 238000005260 corrosion Methods 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 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
- 239000000428 dust Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000004495 emulsifiable concentrate Substances 0.000 description 2
- 239000003995 emulsifying agent Substances 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 235000010755 mineral Nutrition 0.000 description 2
- 208000013435 necrotic lesion Diseases 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 230000001681 protective effect Effects 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 239000011343 solid material Substances 0.000 description 2
- 241000894007 species Species 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 235000015096 spirit Nutrition 0.000 description 2
- 229910052717 sulfur Chemical group 0.000 description 2
- 239000011593 sulfur Chemical group 0.000 description 2
- 239000004546 suspension concentrate Substances 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 125000006700 (C1-C6) alkylthio 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
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- ZHJOQLHRCOXPLV-UHFFFAOYSA-N 1-chloro-2-methylbenzene;hydrochloride Chemical compound Cl.CC1=CC=CC=C1Cl ZHJOQLHRCOXPLV-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
- AVPYQKSLYISFPO-UHFFFAOYSA-N 4-chlorobenzaldehyde Chemical compound ClC1=CC=C(C=O)C=C1 AVPYQKSLYISFPO-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
- 244000105624 Arachis hypogaea Species 0.000 description 1
- 241001480061 Blumeria graminis Species 0.000 description 1
- 241000123650 Botrytis cinerea Species 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
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-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
- 241000221785 Erysiphales Species 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 206010061217 Infestation 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
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 241000315044 Passalora arachidicola Species 0.000 description 1
- CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical group ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 description 1
- 241000233679 Peronosporaceae Species 0.000 description 1
- 241000233622 Phytophthora infestans Species 0.000 description 1
- 241001337928 Podosphaera leucotricha Species 0.000 description 1
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
- 229920002125 Sokalan® Polymers 0.000 description 1
- 240000003768 Solanum lycopersicum Species 0.000 description 1
- 244000061456 Solanum tuberosum Species 0.000 description 1
- 235000002595 Solanum tuberosum Nutrition 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
- 150000007513 acids Chemical class 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
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 125000004171 alkoxy aryl group Chemical group 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 230000002528 anti-freeze Effects 0.000 description 1
- 239000002518 antifoaming agent Substances 0.000 description 1
- 239000010426 asphalt Substances 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 235000013871 bee wax Nutrition 0.000 description 1
- 239000012166 beeswax Substances 0.000 description 1
- TXPVUYLRHHHRLY-UHFFFAOYSA-N benzenecarboximidoyl chloride;hydrochloride Chemical compound Cl.ClC(=N)C1=CC=CC=C1 TXPVUYLRHHHRLY-UHFFFAOYSA-N 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 125000001246 bromo group Chemical group Br* 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 class [Ca+2].OP(O)(O)=O.OP(O)(O)=O YYRMJZQKEFZXMX-UHFFFAOYSA-N 0.000 description 1
- 239000004359 castor oil Substances 0.000 description 1
- 235000019438 castor oil Nutrition 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 239000000084 colloidal system Substances 0.000 description 1
- 239000002361 compost Substances 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 239000006184 cosolvent Substances 0.000 description 1
- 238000005520 cutting process Methods 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
- 239000006185 dispersion Substances 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
- 238000010410 dusting Methods 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 150000002191 fatty alcohols Chemical class 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000003337 fertilizer Substances 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 238000009472 formulation Methods 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
- 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
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 1
- 239000003350 kerosene Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000000391 magnesium silicate Substances 0.000 description 1
- 235000012243 magnesium silicates Nutrition 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000010445 mica Substances 0.000 description 1
- 229910052618 mica group Inorganic materials 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 239000012184 mineral wax Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- 229910052901 montmorillonite Inorganic materials 0.000 description 1
- 125000002757 morpholinyl group Chemical group 0.000 description 1
- 239000000025 natural resin Substances 0.000 description 1
- 231100001184 nonphytotoxic Toxicity 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 230000000149 penetrating effect Effects 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- 238000003359 percent control normalization Methods 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- AFDMODCXODAXLC-UHFFFAOYSA-N phenylmethanimine Chemical compound N=CC1=CC=CC=C1 AFDMODCXODAXLC-UHFFFAOYSA-N 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
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 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
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 238000009666 routine test Methods 0.000 description 1
- 238000004062 sedimentation Methods 0.000 description 1
- 229940080264 sodium dodecylbenzenesulfonate Drugs 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 150000003459 sulfonic acid esters Chemical class 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000002426 superphosphate Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 238000012353 t test Methods 0.000 description 1
- 229950011008 tetrachloroethylene Drugs 0.000 description 1
- 125000004568 thiomorpholinyl group Chemical group 0.000 description 1
- 239000013008 thixotropic agent Substances 0.000 description 1
- 235000019354 vermiculite Nutrition 0.000 description 1
- 239000003039 volatile agent Substances 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000008096 xylene 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
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Environmental Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Plant Pathology (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Pyridine Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Indole Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB7908822 | 1979-03-13 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DD149452A5 true DD149452A5 (de) | 1981-07-15 |
Family
ID=10503839
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD80219586A DD149452A5 (de) | 1979-03-13 | 1980-03-11 | Fungizide zusammensetzung |
| DD80227941A DD156563A5 (de) | 1979-03-13 | 1980-03-11 | Verfahren zur herstellung von pyridyliminomethylbenzolderivaten |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD80227941A DD156563A5 (de) | 1979-03-13 | 1980-03-11 | Verfahren zur herstellung von pyridyliminomethylbenzolderivaten |
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 |
| EP0422848A1 (en) * | 1989-10-09 | 1991-04-17 | Imperial Chemical Industries Plc | Fungicides |
| GB8922691D0 (en) * | 1989-10-09 | 1989-11-22 | Ici Plc | Fungicides |
| KR0160142B1 (ko) * | 1990-05-31 | 1998-12-01 | 알렌 제이. 스피겔 | 치환된 피페리딘의 제조방법 |
| US5364943A (en) * | 1991-11-27 | 1994-11-15 | Pfizer Inc. | Preparation of substituted piperidines |
| GB9024873D0 (en) * | 1990-11-15 | 1991-01-02 | Ici Plc | Fungicidal compounds |
| CA2134964C (en) * | 1992-05-18 | 1997-12-30 | Manoj C. Desai | Bridged aza-bicyclic derivatives as substance p antagonists |
| CA2141051A1 (en) * | 1992-08-04 | 1994-02-17 | Terry J. Rosen | Substituted nitrogen-containing heterocycles |
| RU2532135C2 (ru) * | 2007-02-22 | 2014-10-27 | Зингента Партисипейшнс Аг | Производные иминопиридина и их применение в качестве микробиоцидов |
| EP2264011A1 (de) * | 2009-06-03 | 2010-12-22 | Bayer CropScience AG | Heteroarylamidine und deren Verwendung als Fungizide |
| EP2264012A1 (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 |
| NL218635A (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 DE DE8080200212T patent/DE3070045D1/de not_active Expired
- 1980-03-06 AT AT80200212T patent/ATE11483T1/de not_active IP Right Cessation
- 1980-03-06 EP EP80200212A patent/EP0015628B1/en not_active Expired
- 1980-03-11 JP JP2985580A patent/JPS55124764A/ja active Granted
- 1980-03-11 BR BR8001433A patent/BR8001433A/pt not_active IP Right Cessation
- 1980-03-11 IL IL59586A patent/IL59586A/xx not_active IP Right Cessation
- 1980-03-11 DD DD80219586A patent/DD149452A5/de not_active IP Right Cessation
- 1980-03-11 ZA ZA00801413A patent/ZA801413B/xx unknown
- 1980-03-11 DK DK104980A patent/DK159423C/da not_active IP Right Cessation
- 1980-03-11 BG BG049336A patent/BG31498A3/xx unknown
- 1980-03-11 MX MX808703U patent/MX5868E/es unknown
- 1980-03-11 TR TR21441A patent/TR21441A/xx unknown
- 1980-03-11 BG BG046940A patent/BG31473A3/xx unknown
- 1980-03-11 SU SU802891905A patent/SU1281153A3/ru active
- 1980-03-11 NZ NZ193094A patent/NZ193094A/xx unknown
- 1980-03-11 AU AU56347/80A patent/AU533020B2/en not_active Ceased
- 1980-03-11 OA OA57050A patent/OA06485A/xx unknown
- 1980-03-11 EG EG142/80A patent/EG14257A/xx active
- 1980-03-11 ES ES489421A patent/ES8104231A1/es not_active Expired
- 1980-03-11 HU HU80570A patent/HU185878B/hu not_active IP Right Cessation
- 1980-03-11 IN IN176/DEL/80A patent/IN153816B/en unknown
- 1980-03-11 DD DD80227941A patent/DD156563A5/de unknown
- 1980-03-11 PL PL1980222598A patent/PL121497B1/pl unknown
- 1980-03-11 IE IE496/80A patent/IE49554B1/en not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| PL121497B1 (en) | 1982-05-31 |
| DK159423C (da) | 1991-03-18 |
| JPS6348866B2 (enExample) | 1988-09-30 |
| ATE11483T1 (de) | 1985-02-15 |
| BG31473A3 (en) | 1982-01-15 |
| DK104980A (da) | 1980-09-14 |
| IL59586A (en) | 1984-05-31 |
| JPS55124764A (en) | 1980-09-26 |
| IE800496L (en) | 1980-09-13 |
| BR8001433A (pt) | 1980-11-11 |
| BG31498A3 (en) | 1982-01-15 |
| PL222598A1 (enExample) | 1980-12-15 |
| EG14257A (en) | 1983-09-30 |
| EP0015628B1 (en) | 1985-01-30 |
| IN153816B (enExample) | 1984-08-18 |
| SU1281153A3 (ru) | 1986-12-30 |
| ZA801413B (en) | 1981-03-25 |
| DK159423B (da) | 1990-10-15 |
| CA1160229A (en) | 1984-01-10 |
| MX5868E (es) | 1984-08-15 |
| AU533020B2 (en) | 1983-10-27 |
| IL59586A0 (en) | 1980-06-30 |
| TR21441A (tr) | 1984-06-04 |
| OA06485A (fr) | 1981-07-31 |
| IE49554B1 (en) | 1985-10-30 |
| ES489421A0 (es) | 1981-04-01 |
| ES8104231A1 (es) | 1981-04-01 |
| DD156563A5 (de) | 1982-09-08 |
| AU5634780A (en) | 1980-09-18 |
| HU185878B (en) | 1985-04-28 |
| DE3070045D1 (en) | 1985-03-14 |
| PH17400A (en) | 1984-08-08 |
| NZ193094A (en) | 1982-08-17 |
| EP0015628A1 (en) | 1980-09-17 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE69406538T2 (de) | Dihalotriazolopyrimidinderivate als fugizide | |
| DE69222746T2 (de) | Triazolopyrimidinderivate mit fungizider Aktivität | |
| DE69317439T2 (de) | Azoxycyanbenzol-Derivate | |
| EP0144748A2 (de) | Imidazolinone, Verfahren zur ihrer Herstellung und ihre Verwendung im Pflanzenschutz | |
| DD149452A5 (de) | Fungizide zusammensetzung | |
| CH647649A5 (de) | Verfahren zur bekaempfung von pilzen und/oder bekaempfung oder regulierung des pflanzenwachstums. | |
| DE2639189A1 (de) | 3-pyridyl-isoxazolidine | |
| EP0133247A2 (de) | N-Aminomethyl-3-phenyl-4-cyanopyrrol-Derivate, deren Herstellung und Verwendung als Mikrobizide | |
| DD148289A5 (de) | Herbizide zusammensetzungen und verfahren zur bekaempfung unerwuenschten pflanzenwuchses | |
| DE69012197T2 (de) | Thiazol-Derivate. | |
| DE3614060A1 (de) | Pyrimidin-derivate, verfahren zu ihrer herstellung und ihre verwendung als fungizide | |
| EP0037971B1 (de) | Trisubstituierte Cyanguanidine, Verfahren zu ihrer Herstellung sowie ihre Verwendung als Fungizide | |
| DD222766A5 (de) | Mikrobizides mittel | |
| DE69017971T2 (de) | Biozide Verbindungen. | |
| DD223907A5 (de) | Pestizide zusammensetzungen | |
| DE2054512A1 (de) | Pyranverbindungen, Verfahren zu ih rer Herstellung und ihre Verwendung als Pflanzenschutzmittel | |
| DE69014705T2 (de) | Thiazol-Derivate. | |
| DD145222A5 (de) | Pestizide und/oder wachstumsregulierende zusammensetzungen | |
| EP0075172B1 (de) | N-Sulfenylierte Benzylsulfonamide, ein Verfahren und ihre Verwendung als Mikrobizide | |
| DD240494A5 (de) | Pestizide zusammensetzung | |
| DE2703023A1 (de) | Furanderivate | |
| DE2808842A1 (de) | 1,3,4-oxadiazolverbindungen, deren herstellung und ihre verwendung | |
| DD262025A5 (de) | Imidazol-derivate | |
| DD273252A5 (de) | Verfahren zur herstellung von imidazolderivaten und diese derivate enthaltende fungizide zusammensetzung | |
| DD209566A5 (de) | Fungizide zusammensetzungen |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| ENJ | Ceased due to non-payment of renewal fee |