CS241547B2 - Fungicide and method of active component production - Google Patents
Fungicide and method of active component production Download PDFInfo
- Publication number
- CS241547B2 CS241547B2 CS844412A CS441284A CS241547B2 CS 241547 B2 CS241547 B2 CS 241547B2 CS 844412 A CS844412 A CS 844412A CS 441284 A CS441284 A CS 441284A CS 241547 B2 CS241547 B2 CS 241547B2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- group
- cyanopyrrole
- formula
- alkyl
- carbon atoms
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 21
- 230000000855 fungicidal effect Effects 0.000 title claims description 13
- 239000000417 fungicide Substances 0.000 title description 4
- 238000004519 manufacturing process Methods 0.000 title description 3
- -1 2-tetrahydrofuryl Chemical group 0.000 claims abstract description 67
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims abstract description 27
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 26
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 25
- 239000001257 hydrogen Substances 0.000 claims abstract description 25
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 19
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims abstract description 17
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 17
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 16
- 150000002367 halogens Chemical class 0.000 claims abstract description 15
- 125000001188 haloalkyl group Chemical group 0.000 claims abstract description 9
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 7
- 125000000304 alkynyl group Chemical group 0.000 claims abstract description 7
- 229910052717 sulfur Chemical group 0.000 claims abstract description 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 5
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 5
- 239000001301 oxygen Substances 0.000 claims abstract description 5
- 239000011593 sulfur Chemical group 0.000 claims abstract description 5
- 150000002431 hydrogen Chemical class 0.000 claims abstract 7
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract 6
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims abstract 3
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims abstract 3
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims abstract 2
- 150000001875 compounds Chemical class 0.000 claims description 117
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 104
- 239000000203 mixture Substances 0.000 claims description 56
- 239000004480 active ingredient Substances 0.000 claims description 43
- 125000004432 carbon atom Chemical group C* 0.000 claims description 39
- 125000000217 alkyl group Chemical group 0.000 claims description 27
- 238000002360 preparation method Methods 0.000 claims description 22
- 239000002253 acid Substances 0.000 claims description 20
- 238000006243 chemical reaction Methods 0.000 claims description 20
- 229910052801 chlorine Inorganic materials 0.000 claims description 16
- 239000002904 solvent Substances 0.000 claims description 16
- 239000000460 chlorine Substances 0.000 claims description 15
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 12
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 12
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 12
- 229910052794 bromium Inorganic materials 0.000 claims description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
- 125000003545 alkoxy group Chemical group 0.000 claims description 11
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
- 239000011737 fluorine Substances 0.000 claims description 10
- 229910052731 fluorine Inorganic materials 0.000 claims description 10
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 8
- 239000003795 chemical substances by application Substances 0.000 claims description 8
- 125000005843 halogen group Chemical group 0.000 claims description 8
- 239000007858 starting material Substances 0.000 claims description 8
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 7
- 150000003839 salts Chemical class 0.000 claims description 7
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 6
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 5
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 5
- 239000003054 catalyst Substances 0.000 claims description 5
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 4
- 239000012442 inert solvent Substances 0.000 claims description 4
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 claims description 4
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims description 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 3
- MTDPTPLVUWOKBV-UHFFFAOYSA-N [3-cyano-4-(2,3-dichlorophenyl)pyrrol-1-yl]methyl 2-methoxyacetate Chemical compound COCC(=O)OCN1C=C(C#N)C(C=2C(=C(Cl)C=CC=2)Cl)=C1 MTDPTPLVUWOKBV-UHFFFAOYSA-N 0.000 claims description 3
- 230000002378 acidificating effect Effects 0.000 claims description 3
- 125000004423 acyloxy group Chemical group 0.000 claims description 3
- 125000004429 atom Chemical group 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 2
- 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 claims description 2
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims description 2
- IDKAZXAZEPLYJH-UHFFFAOYSA-N 4-(2-chlorophenyl)-1-(2-methoxyacetyl)pyrrole-3-carbonitrile Chemical compound COCC(=O)N1C=C(C#N)C(C=2C(=CC=CC=2)Cl)=C1 IDKAZXAZEPLYJH-UHFFFAOYSA-N 0.000 claims description 2
- FERAMOFNROYERF-UHFFFAOYSA-N 4-(3-methoxyphenyl)-1-(2,2,2-trichloro-1-hydroxyethyl)pyrrole-3-carbonitrile Chemical compound COC1=CC=CC(C=2C(=CN(C=2)C(O)C(Cl)(Cl)Cl)C#N)=C1 FERAMOFNROYERF-UHFFFAOYSA-N 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 239000007809 chemical reaction catalyst Substances 0.000 claims description 2
- 230000002140 halogenating effect Effects 0.000 claims description 2
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 2
- CWUNWBTXKMJWBJ-UHFFFAOYSA-N 1-(chloromethyl)-4-(3-methoxyphenyl)pyrrole-3-carbonitrile Chemical compound COC1=CC=CC(C=2C(=CN(CCl)C=2)C#N)=C1 CWUNWBTXKMJWBJ-UHFFFAOYSA-N 0.000 claims 2
- 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 claims 2
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims 2
- 125000006583 (C1-C3) haloalkyl group Chemical group 0.000 claims 1
- 125000006648 (C1-C8) haloalkyl group Chemical group 0.000 claims 1
- UMPSXRYVXUPCOS-UHFFFAOYSA-N 2,3-dichlorophenol Chemical compound OC1=CC=CC(Cl)=C1Cl UMPSXRYVXUPCOS-UHFFFAOYSA-N 0.000 claims 1
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims 1
- UNUVTWHLMXJZLN-UHFFFAOYSA-N 4-(2,3-dichlorophenyl)-1-(2,2,2-trichloro-1-hydroxyethyl)pyrrole-3-carbonitrile Chemical compound ClC(Cl)(Cl)C(O)N1C=C(C#N)C(C=2C(=C(Cl)C=CC=2)Cl)=C1 UNUVTWHLMXJZLN-UHFFFAOYSA-N 0.000 claims 1
- MFZJBKYTIXLYLG-UHFFFAOYSA-N 4-(2-chlorophenyl)-1-(2,2,2-trichloro-1-hydroxyethyl)pyrrole-3-carbonitrile Chemical compound ClC(Cl)(Cl)C(O)N1C=C(C#N)C(C=2C(=CC=CC=2)Cl)=C1 MFZJBKYTIXLYLG-UHFFFAOYSA-N 0.000 claims 1
- WVVPTEOHWXPIND-UHFFFAOYSA-N 4-(2-methoxyphenyl)-1-(2,2,2-trichloro-1-hydroxyethyl)pyrrole-3-carbonitrile Chemical compound COC1=CC=CC=C1C1=CN(C(O)C(Cl)(Cl)Cl)C=C1C#N WVVPTEOHWXPIND-UHFFFAOYSA-N 0.000 claims 1
- YUUQXEMDGIZKIL-UHFFFAOYSA-N 4-(3-chlorophenyl)-1-(hydroxymethyl)pyrrole-3-carbonitrile Chemical compound OCN1C=C(C#N)C(C=2C=C(Cl)C=CC=2)=C1 YUUQXEMDGIZKIL-UHFFFAOYSA-N 0.000 claims 1
- YSMODUONRAFBET-UHFFFAOYSA-N 5-hydroxylysine Chemical group NCC(O)CCC(N)C(O)=O YSMODUONRAFBET-UHFFFAOYSA-N 0.000 claims 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- YZCKVEUIGOORGS-NJFSPNSNSA-N Tritium Chemical group [3H] YZCKVEUIGOORGS-NJFSPNSNSA-N 0.000 claims 1
- UTMSZAFYLHAZNR-UHFFFAOYSA-N [2,2,2-trichloro-1-[3-cyano-4-(2,3-dichlorophenyl)pyrrol-1-yl]ethyl] 2-prop-2-ynoxyacetate Chemical compound ClC1=CC=CC(C=2C(=CN(C=2)C(OC(=O)COCC#C)C(Cl)(Cl)Cl)C#N)=C1Cl UTMSZAFYLHAZNR-UHFFFAOYSA-N 0.000 claims 1
- DANNULXKBIPZCA-UHFFFAOYSA-N [2,2,2-trichloro-1-[3-cyano-4-(2-methylsulfanylphenyl)pyrrol-1-yl]ethyl] 2-methoxyacetate Chemical compound COCC(=O)OC(C(Cl)(Cl)Cl)N1C=C(C#N)C(C=2C(=CC=CC=2)SC)=C1 DANNULXKBIPZCA-UHFFFAOYSA-N 0.000 claims 1
- 239000003513 alkali Substances 0.000 claims 1
- 125000005708 carbonyloxy group Chemical group [*:2]OC([*:1])=O 0.000 claims 1
- 125000000068 chlorophenyl group Chemical group 0.000 claims 1
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 1
- ZZHGIUCYKGFIPV-UHFFFAOYSA-M n-butylcarbamate Chemical compound CCCCNC([O-])=O ZZHGIUCYKGFIPV-UHFFFAOYSA-M 0.000 claims 1
- 125000004430 oxygen atom Chemical group O* 0.000 claims 1
- 125000004434 sulfur atom Chemical group 0.000 claims 1
- 244000005700 microbiome Species 0.000 abstract description 7
- 230000003032 phytopathogenic effect Effects 0.000 abstract description 6
- BMMCNKYHQAKJBN-UHFFFAOYSA-N 4-phenyl-1h-pyrrole-3-carbonitrile Chemical class N#CC1=CNC=C1C1=CC=CC=C1 BMMCNKYHQAKJBN-UHFFFAOYSA-N 0.000 abstract description 5
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 abstract description 2
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 abstract description 2
- 239000002855 microbicide agent Substances 0.000 abstract 1
- 241000196324 Embryophyta Species 0.000 description 50
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 46
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 30
- 239000013543 active substance Substances 0.000 description 26
- 239000000243 solution Substances 0.000 description 23
- 239000000725 suspension Substances 0.000 description 23
- 241000233866 Fungi Species 0.000 description 22
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 22
- 230000000694 effects Effects 0.000 description 22
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
- 238000012360 testing method Methods 0.000 description 17
- 230000002538 fungal effect Effects 0.000 description 15
- 239000004563 wettable powder Substances 0.000 description 15
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- 239000000126 substance Substances 0.000 description 14
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- 235000013339 cereals Nutrition 0.000 description 13
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- RPXCCPFIMAPSKP-UHFFFAOYSA-N dimethylamino dihydrogen phosphate Chemical compound CN(C)OP(O)(O)=O RPXCCPFIMAPSKP-UHFFFAOYSA-N 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
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- ZGSPNIOCEDOHGS-UHFFFAOYSA-L disodium [3-[2,3-di(octadeca-9,12-dienoyloxy)propoxy-oxidophosphoryl]oxy-2-hydroxypropyl] 2,3-di(octadeca-9,12-dienoyloxy)propyl phosphate Chemical compound [Na+].[Na+].CCCCCC=CCC=CCCCCCCCC(=O)OCC(OC(=O)CCCCCCCC=CCC=CCCCCC)COP([O-])(=O)OCC(O)COP([O-])(=O)OCC(OC(=O)CCCCCCCC=CCC=CCCCCC)COC(=O)CCCCCCCC=CCC=CCCCCC ZGSPNIOCEDOHGS-UHFFFAOYSA-L 0.000 description 1
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- KWKXNDCHNDYVRT-UHFFFAOYSA-N dodecylbenzene Chemical compound CCCCCCCCCCCCC1=CC=CC=C1 KWKXNDCHNDYVRT-UHFFFAOYSA-N 0.000 description 1
- 239000010459 dolomite Substances 0.000 description 1
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- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
- FKLFBQCQQYDUAM-UHFFFAOYSA-N fenpiclonil Chemical compound ClC1=CC=CC(C=2C(=CNC=2)C#N)=C1Cl FKLFBQCQQYDUAM-UHFFFAOYSA-N 0.000 description 1
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- 239000004467 fishmeal Substances 0.000 description 1
- 235000012055 fruits and vegetables Nutrition 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
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- 210000002216 heart Anatomy 0.000 description 1
- 239000012760 heat stabilizer Substances 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- OHMBHFSEKCCCBW-UHFFFAOYSA-N hexane-2,5-diol Chemical compound CC(O)CCC(C)O OHMBHFSEKCCCBW-UHFFFAOYSA-N 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000003898 horticulture Methods 0.000 description 1
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 239000003701 inert diluent Substances 0.000 description 1
- 208000014674 injury Diseases 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000000787 lecithin Substances 0.000 description 1
- 235000010445 lecithin Nutrition 0.000 description 1
- 235000021374 legumes Nutrition 0.000 description 1
- 230000003902 lesion Effects 0.000 description 1
- 239000012669 liquid formulation Substances 0.000 description 1
- 150000002642 lithium compounds Chemical class 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 210000004072 lung Anatomy 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
- 239000001095 magnesium carbonate Substances 0.000 description 1
- 229910000021 magnesium carbonate Inorganic materials 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 235000013372 meat Nutrition 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- JZMJDSHXVKJFKW-UHFFFAOYSA-N methyl sulfate Chemical class COS(O)(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-N 0.000 description 1
- 125000004092 methylthiomethyl group Chemical group [H]C([H])([H])SC([H])([H])* 0.000 description 1
- 230000003641 microbiacidal effect Effects 0.000 description 1
- 235000019713 millet Nutrition 0.000 description 1
- 239000003750 molluscacide Substances 0.000 description 1
- 230000002013 molluscicidal effect Effects 0.000 description 1
- ODKLEQPZOCJQMT-UHFFFAOYSA-N n,n-diethylpyridin-4-amine Chemical compound CCN(CC)C1=CC=NC=C1 ODKLEQPZOCJQMT-UHFFFAOYSA-N 0.000 description 1
- DAZXVJBJRMWXJP-UHFFFAOYSA-N n,n-dimethylethylamine Chemical compound CCN(C)C DAZXVJBJRMWXJP-UHFFFAOYSA-N 0.000 description 1
- 239000005445 natural material Substances 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- 239000005645 nematicide Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 235000014571 nuts Nutrition 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical class CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Chemical class CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical class CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 150000002924 oxiranes Chemical class 0.000 description 1
- 229910052625 palygorskite Inorganic materials 0.000 description 1
- 235000020232 peanut Nutrition 0.000 description 1
- 235000021017 pears Nutrition 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000008104 phosphatidylethanolamines Chemical class 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 150000003014 phosphoric acid esters Chemical class 0.000 description 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 238000005554 pickling Methods 0.000 description 1
- 230000008635 plant growth Effects 0.000 description 1
- 235000021018 plums Nutrition 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000002685 polymerization catalyst Substances 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 235000012015 potatoes Nutrition 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 239000008262 pumice Substances 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 235000003441 saturated fatty acids Nutrition 0.000 description 1
- 150000004671 saturated fatty acids Chemical class 0.000 description 1
- 229910052624 sepiolite Inorganic materials 0.000 description 1
- 235000019355 sepiolite Nutrition 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 229920002545 silicone oil Polymers 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000008117 stearic acid Chemical class 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 230000002459 sustained effect Effects 0.000 description 1
- 239000003760 tallow Substances 0.000 description 1
- 235000013616 tea Nutrition 0.000 description 1
- NUMQCACRALPSHD-UHFFFAOYSA-N tert-Butyl ethyl ether Natural products CCOC(C)(C)C NUMQCACRALPSHD-UHFFFAOYSA-N 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229950011008 tetrachloroethylene Drugs 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 239000011573 trace mineral Substances 0.000 description 1
- 235000013619 trace mineral Nutrition 0.000 description 1
- 125000006000 trichloroethyl group Chemical group 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- ZISSAWUMDACLOM-UHFFFAOYSA-N triptane Chemical compound CC(C)C(C)(C)C ZISSAWUMDACLOM-UHFFFAOYSA-N 0.000 description 1
- JABYJIQOLGWMQW-UHFFFAOYSA-N undec-4-ene Chemical compound CCCCCCC=CCCC JABYJIQOLGWMQW-UHFFFAOYSA-N 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- 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
- A01N43/36—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom five-membered rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/34—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members 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
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth 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)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Pyrrole Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH333183 | 1983-06-17 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CS441284A2 CS441284A2 (en) | 1985-07-16 |
| CS241547B2 true CS241547B2 (en) | 1986-03-13 |
Family
ID=4253654
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS844412A CS241547B2 (en) | 1983-06-17 | 1984-06-12 | Fungicide and method of active component production |
Country Status (24)
| Country | Link |
|---|---|
| EP (1) | EP0130149B1 (en)van) |
| JP (1) | JPS6016970A (en)van) |
| KR (1) | KR910003346B1 (en)van) |
| AR (1) | AR240802A1 (en)van) |
| AU (1) | AU570047B2 (en)van) |
| BG (1) | BG43855A3 (en)van) |
| BR (1) | BR8402938A (en)van) |
| CS (1) | CS241547B2 (en)van) |
| DD (1) | DD222766A5 (en)van) |
| DE (1) | DE3477662D1 (en)van) |
| DK (1) | DK294684A (en)van) |
| ES (2) | ES8602650A1 (en)van) |
| FI (1) | FI80441C (en)van) |
| GB (1) | GB2141709B (en)van) |
| GR (1) | GR82159B (en)van) |
| HU (1) | HU194022B (en)van) |
| IL (1) | IL72121A (en)van) |
| MA (1) | MA20154A1 (en)van) |
| NO (1) | NO842422L (en)van) |
| PH (1) | PH21414A (en)van) |
| PL (1) | PL141650B1 (en)van) |
| PT (1) | PT78722A (en)van) |
| TR (1) | TR21812A (en)van) |
| ZA (1) | ZA844539B (en)van) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4546099A (en) * | 1983-07-22 | 1985-10-08 | Ciba-Geigy Corporation | N-Aminomethyl-3-phenyl-4-cyanopyrrole derivatives, compositions and use thereof as microbicides |
| US4705800A (en) * | 1985-06-21 | 1987-11-10 | Ciba-Geigy Corporation | Difluorbenzodioxyl cyanopyrrole microbicidal compositions |
| US5455263A (en) * | 1987-07-29 | 1995-10-03 | American Cyanamid Company | Methods for the control and the protection of warm-blooded animals against infestation and infection by helminths, acarids and arthropod endo- and ectoparasites |
| US5010098A (en) * | 1987-07-29 | 1991-04-23 | American Cyanamid Company | Arylpyrrole insecticidal acaricidal and nematicidal agents and methods for the preparation thereof |
| DE3804128A1 (de) * | 1988-02-11 | 1989-08-24 | Bayer Ag | 1-aminomethyl-3-(2-fluor-3-chlorphenyl)-4-cyano-pyrrol-derivate |
| DE3814478A1 (de) * | 1988-04-29 | 1989-11-09 | Bayer Ag | 3-cyano-4-phenyl-pyrrole, verfahren zu ihrer herstellung und ihre verwendung in schaedlingsbekaempfungsmitteln |
| US5191444A (en) * | 1988-06-20 | 1993-03-02 | Sanyo Electric Co., Ltd. | Method of converting gradation of a digital image and a circuit thereof and a print density controlling apparatus for a printer and a printer using this method |
| EP0358047A3 (en) * | 1988-09-08 | 1991-05-29 | American Cyanamid Company | Method of controlling phytopathogenic fungi |
| DE3922104A1 (de) * | 1989-07-05 | 1991-01-17 | Bayer Ag | N-vinyl-3-cyano-4-phenyl-pyrrol-derivate |
| US5151536A (en) * | 1990-12-17 | 1992-09-29 | American Cyanamid Company | Process for the manufacture of pesticidal 1-(alkoxymethyl) pyrrole compounds |
| ES2449194T3 (es) * | 2000-01-19 | 2014-03-18 | Cadila Healthcare Limited | Compuestos que tienen actividades hipolipidémica e hipocolesterolémica, procedimiento para su preparación y composiciones farmacéuticas que los contienen |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL56243A (en) * | 1978-01-31 | 1982-07-30 | Nippon Soda Co | Phenylpyrrole derivatives,their production and their use as fungicides |
| JPS5511524A (en) * | 1978-07-10 | 1980-01-26 | Nippon Soda Co Ltd | Cyanopyrrole derivative, its preparation and agricultural and horticultural fungicide |
| US4303667A (en) * | 1979-05-25 | 1981-12-01 | Nippon Soda Company Limited | Phenylprrole derivatives |
| US4471126A (en) * | 1982-04-26 | 1984-09-11 | Nippon Soda Company Limited | Method for the production of 3-phenylpyrrole |
| US4546099A (en) * | 1983-07-22 | 1985-10-08 | Ciba-Geigy Corporation | N-Aminomethyl-3-phenyl-4-cyanopyrrole derivatives, compositions and use thereof as microbicides |
| EP0182737A3 (de) * | 1984-10-16 | 1986-10-08 | Ciba-Geigy Ag | 3-Phenylpyrrolderivate, Verfahren zu ihrer Herstellung und ihre Verwendung als Schädlingsbekämpfungsmittel |
| US4705801A (en) * | 1984-10-16 | 1987-11-10 | Ciba-Geigy Corporation | Production for producing 3-cyano-4-phenyl indoles and intermediates |
-
1984
- 1984-06-12 DE DE8484810289T patent/DE3477662D1/de not_active Expired
- 1984-06-12 EP EP84810289A patent/EP0130149B1/de not_active Expired
- 1984-06-12 BG BG065832A patent/BG43855A3/xx unknown
- 1984-06-12 PT PT78722A patent/PT78722A/pt not_active IP Right Cessation
- 1984-06-12 CS CS844412A patent/CS241547B2/cs unknown
- 1984-06-13 GB GB08415032A patent/GB2141709B/en not_active Expired
- 1984-06-15 ZA ZA844539A patent/ZA844539B/xx unknown
- 1984-06-15 PH PH30826A patent/PH21414A/en unknown
- 1984-06-15 GR GR75031A patent/GR82159B/el unknown
- 1984-06-15 FI FI842443A patent/FI80441C/fi not_active IP Right Cessation
- 1984-06-15 AU AU29427/84A patent/AU570047B2/en not_active Ceased
- 1984-06-15 BR BR8402938A patent/BR8402938A/pt unknown
- 1984-06-15 NO NO842422A patent/NO842422L/no unknown
- 1984-06-15 IL IL72121A patent/IL72121A/xx not_active IP Right Cessation
- 1984-06-15 DK DK294684A patent/DK294684A/da not_active Application Discontinuation
- 1984-06-15 HU HU842319A patent/HU194022B/hu not_active IP Right Cessation
- 1984-06-15 TR TR21812A patent/TR21812A/xx unknown
- 1984-06-15 PL PL1984248235A patent/PL141650B1/pl unknown
- 1984-06-15 DD DD84264191A patent/DD222766A5/de not_active IP Right Cessation
- 1984-06-16 ES ES533497A patent/ES8602650A1/es not_active Expired
- 1984-06-16 KR KR1019840003399A patent/KR910003346B1/ko not_active Expired
- 1984-06-16 JP JP59124368A patent/JPS6016970A/ja active Pending
- 1984-06-18 AR AR296929A patent/AR240802A1/es active
- 1984-06-18 MA MA20378A patent/MA20154A1/fr unknown
-
1985
- 1985-08-01 ES ES546506A patent/ES8604717A1/es not_active Expired
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