CH639372A5 - Aromatisch substituierte pyrrolderivate, verfahren zu deren herstellung, diese enthaltende fungizide zusammensetzungen und verfahren zur bekaempfung von pilzen. - Google Patents
Aromatisch substituierte pyrrolderivate, verfahren zu deren herstellung, diese enthaltende fungizide zusammensetzungen und verfahren zur bekaempfung von pilzen. Download PDFInfo
- Publication number
- CH639372A5 CH639372A5 CH52479A CH52479A CH639372A5 CH 639372 A5 CH639372 A5 CH 639372A5 CH 52479 A CH52479 A CH 52479A CH 52479 A CH52479 A CH 52479A CH 639372 A5 CH639372 A5 CH 639372A5
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- Switzerland
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- 239000000203 mixture Substances 0.000 title claims description 32
- 238000000034 method Methods 0.000 title claims description 19
- 230000000855 fungicidal effect Effects 0.000 title claims description 13
- 241000233866 Fungi Species 0.000 title claims description 5
- 239000000417 fungicide Substances 0.000 title description 3
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical class C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 71
- 238000002360 preparation method Methods 0.000 claims description 18
- 239000012876 carrier material Substances 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 4
- 239000012442 inert solvent Substances 0.000 claims description 4
- 239000007858 starting material Substances 0.000 claims description 3
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 16
- -1 acetyl halides Chemical class 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 11
- 238000002844 melting Methods 0.000 description 10
- 230000008018 melting Effects 0.000 description 10
- 239000000126 substance Substances 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 8
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 8
- XDYMNMBJSGHQNH-UHFFFAOYSA-N 3-chloro-4-(2,3-dichlorophenyl)-1h-pyrrole Chemical compound ClC1=CNC=C1C1=CC=CC(Cl)=C1Cl XDYMNMBJSGHQNH-UHFFFAOYSA-N 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- VIHYIVKEECZGOU-UHFFFAOYSA-N N-acetylimidazole Chemical compound CC(=O)N1C=CN=C1 VIHYIVKEECZGOU-UHFFFAOYSA-N 0.000 description 7
- 238000009472 formulation Methods 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- QPLDLSVMHZLSFG-UHFFFAOYSA-N Copper oxide Chemical compound [Cu]=O QPLDLSVMHZLSFG-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 244000046052 Phaseolus vulgaris Species 0.000 description 6
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 6
- 239000004480 active ingredient Substances 0.000 description 6
- 239000013078 crystal Substances 0.000 description 6
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 6
- 201000010099 disease Diseases 0.000 description 6
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- 241000196324 Embryophyta Species 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- 239000000428 dust Substances 0.000 description 5
- 239000004495 emulsifiable concentrate Substances 0.000 description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 5
- GSSXLFACIJSBOM-UHFFFAOYSA-N 2h-pyran-2-ol Chemical class OC1OC=CC=C1 GSSXLFACIJSBOM-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 240000008067 Cucumis sativus Species 0.000 description 4
- 240000005979 Hordeum vulgare Species 0.000 description 4
- 235000007340 Hordeum vulgare Nutrition 0.000 description 4
- 235000010627 Phaseolus vulgaris Nutrition 0.000 description 4
- 231100000674 Phytotoxicity Toxicity 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 239000010410 layer Substances 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- 235000010799 Cucumis sativus var sativus Nutrition 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 238000004587 chromatography analysis Methods 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 239000004615 ingredient Substances 0.000 description 3
- 238000011081 inoculation Methods 0.000 description 3
- LKPLKUMXSAEKID-UHFFFAOYSA-N pentachloronitrobenzene Chemical compound [O-][N+](=O)C1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl LKPLKUMXSAEKID-UHFFFAOYSA-N 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
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- 239000002689 soil Substances 0.000 description 3
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- BQURLQPMCRDHGD-UHFFFAOYSA-N 10-chloro-1-(3-chloro-2-nitrophenyl)pyrene Chemical compound [N+](=O)([O-])C1=C(C=CC=C1Cl)C=1C=CC2=CC=C3C=CC=C4C=C(C=1C2=C43)Cl BQURLQPMCRDHGD-UHFFFAOYSA-N 0.000 description 2
- BRLLTRMNZFJPNQ-UHFFFAOYSA-N 2-(methylamino)-4-oxobutanoic acid Chemical compound CNC(C(O)=O)CC=O BRLLTRMNZFJPNQ-UHFFFAOYSA-N 0.000 description 2
- GSCFNBAEGLQVGU-UHFFFAOYSA-N 3-chloro-4-(2,3-dichlorophenyl)-1h-pyrrole-2,5-dicarboxylic acid Chemical compound ClC1=C(C(=O)O)NC(C(O)=O)=C1C1=CC=CC(Cl)=C1Cl GSCFNBAEGLQVGU-UHFFFAOYSA-N 0.000 description 2
- JESWMZDSDIYPEG-UHFFFAOYSA-N 3-chloro-4-[3-(trifluoromethyl)phenyl]-1h-pyrrole Chemical compound FC(F)(F)C1=CC=CC(C=2C(=CNC=2)Cl)=C1 JESWMZDSDIYPEG-UHFFFAOYSA-N 0.000 description 2
- YFEXNTQIMWSPMH-UHFFFAOYSA-N 4-chloro-3-(3,4-dichlorophenyl)-2h-pyran-2-ol Chemical compound OC1OC=CC(Cl)=C1C1=CC=C(Cl)C(Cl)=C1 YFEXNTQIMWSPMH-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- 241000123650 Botrytis cinerea Species 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- VQXZGZPEZBQXFZ-UHFFFAOYSA-N Helminthosporal Natural products CC(C)C1CCC2(C)C(C)=C(C=O)C1C2C=O VQXZGZPEZBQXFZ-UHFFFAOYSA-N 0.000 description 2
- 239000005909 Kieselgur Substances 0.000 description 2
- 240000007594 Oryza sativa Species 0.000 description 2
- 235000007164 Oryza sativa Nutrition 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 241000209140 Triticum Species 0.000 description 2
- 235000021307 Triticum Nutrition 0.000 description 2
- 238000006640 acetylation reaction Methods 0.000 description 2
- 239000007900 aqueous suspension Substances 0.000 description 2
- GYSSRZJIHXQEHQ-UHFFFAOYSA-N carboxin Chemical compound S1CCOC(C)=C1C(=O)NC1=CC=CC=C1 GYSSRZJIHXQEHQ-UHFFFAOYSA-N 0.000 description 2
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- XWXFDNURJZGGOB-UHFFFAOYSA-N ethyl 4-(2,3-dichlorophenyl)-2,4-dioxobutanoate Chemical compound CCOC(=O)C(=O)CC(=O)C1=CC=CC(Cl)=C1Cl XWXFDNURJZGGOB-UHFFFAOYSA-N 0.000 description 2
- 230000002538 fungal effect Effects 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- VQXZGZPEZBQXFZ-BEAPCOKYSA-N helminthosporal Chemical compound CC(C)[C@H]1CC[C@@]2(C)C(C)=C(C=O)[C@@H]1[C@@H]2C=O VQXZGZPEZBQXFZ-BEAPCOKYSA-N 0.000 description 2
- 235000021332 kidney beans Nutrition 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
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- KMABBMYSEVZARZ-UHFFFAOYSA-N 1-(2,3-dichlorophenyl)ethanone Chemical compound CC(=O)C1=CC=CC(Cl)=C1Cl KMABBMYSEVZARZ-UHFFFAOYSA-N 0.000 description 1
- PBNAJKPBDGYBDE-UHFFFAOYSA-N 1-[4-chloro-3-(2-chlorophenyl)pyren-1-yl]ethanone Chemical compound C(C)(=O)C1=CC(=C2C(=CC3=CC=CC4=CC=C1C2=C34)Cl)C1=C(C=CC=C1)Cl PBNAJKPBDGYBDE-UHFFFAOYSA-N 0.000 description 1
- YBKNRRXQSIKIDB-UHFFFAOYSA-N 1-[4-chloro-3-(3-chloro-2-nitrophenyl)pyren-1-yl]ethanone Chemical compound C(C)(=O)C1=CC(=C2C(=CC3=CC=CC4=CC=C1C2=C34)Cl)C1=C(C(=CC=C1)Cl)[N+](=O)[O-] YBKNRRXQSIKIDB-UHFFFAOYSA-N 0.000 description 1
- VIOUUHYZUMORJQ-UHFFFAOYSA-N 10-chloro-1-(3-chlorophenyl)pyrene Chemical compound ClC=1C=C(C=CC=1)C=1C=CC2=CC=C3C=CC=C4C=C(C=1C2=C43)Cl VIOUUHYZUMORJQ-UHFFFAOYSA-N 0.000 description 1
- WYIVDYGTKGEJLC-UHFFFAOYSA-N 2,3-dioxobutanoic acid Chemical compound CC(=O)C(=O)C(O)=O WYIVDYGTKGEJLC-UHFFFAOYSA-N 0.000 description 1
- HTMCRAOPSMPUHS-UHFFFAOYSA-N 2-amino-2-methyl-4-oxobutanoic acid Chemical compound OC(=O)C(N)(C)CC=O HTMCRAOPSMPUHS-UHFFFAOYSA-N 0.000 description 1
- IJHLWJZMSWJAQH-UHFFFAOYSA-N 2-aminopropanedioic acid;hydrochloride Chemical compound Cl.OC(=O)C(N)C(O)=O IJHLWJZMSWJAQH-UHFFFAOYSA-N 0.000 description 1
- CVYYIAKFAXYHPW-UHFFFAOYSA-N 4-chloro-3-[3-(trifluoromethyl)phenyl]-2h-pyran-2-ol Chemical compound OC1OC=CC(Cl)=C1C1=CC=CC(C(F)(F)F)=C1 CVYYIAKFAXYHPW-UHFFFAOYSA-N 0.000 description 1
- UHPMCKVQTMMPCG-UHFFFAOYSA-N 5,8-dihydroxy-2-methoxy-6-methyl-7-(2-oxopropyl)naphthalene-1,4-dione Chemical compound CC1=C(CC(C)=O)C(O)=C2C(=O)C(OC)=CC(=O)C2=C1O UHPMCKVQTMMPCG-UHFFFAOYSA-N 0.000 description 1
- XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 1
- 244000144730 Amygdalus persica Species 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 229910021592 Copper(II) chloride Inorganic materials 0.000 description 1
- JPVYNHNXODAKFH-UHFFFAOYSA-N Cu2+ Chemical class [Cu+2] JPVYNHNXODAKFH-UHFFFAOYSA-N 0.000 description 1
- 235000009849 Cucumis sativus Nutrition 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical group CCOC(=O)OCC OIFBSDVPJOWBCH-UHFFFAOYSA-N 0.000 description 1
- 241000223218 Fusarium Species 0.000 description 1
- 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 1
- 235000007688 Lycopersicon esculentum Nutrition 0.000 description 1
- 244000141359 Malus pumila Species 0.000 description 1
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 235000006040 Prunus persica var persica Nutrition 0.000 description 1
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- 206010039509 Scab Diseases 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 240000003768 Solanum lycopersicum Species 0.000 description 1
- 241000219094 Vitaceae Species 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 238000007605 air drying Methods 0.000 description 1
- 150000008051 alkyl sulfates Chemical class 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- 229910052586 apatite Inorganic materials 0.000 description 1
- 235000021016 apples Nutrition 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 239000000440 bentonite Substances 0.000 description 1
- 229910000278 bentonite Inorganic materials 0.000 description 1
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
- 230000003115 biocidal effect Effects 0.000 description 1
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- 239000006227 byproduct Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 235000013339 cereals Nutrition 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 229910052570 clay Inorganic materials 0.000 description 1
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 1
- 229910000366 copper(II) sulfate Inorganic materials 0.000 description 1
- 238000006114 decarboxylation reaction Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- WURGXGVFSMYFCG-UHFFFAOYSA-N dichlofluanid Chemical compound CN(C)S(=O)(=O)N(SC(F)(Cl)Cl)C1=CC=CC=C1 WURGXGVFSMYFCG-UHFFFAOYSA-N 0.000 description 1
- WYACBZDAHNBPPB-UHFFFAOYSA-N diethyl oxalate Chemical compound CCOC(=O)C(=O)OCC WYACBZDAHNBPPB-UHFFFAOYSA-N 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- FDPIMTJIUBPUKL-UHFFFAOYSA-N dimethylacetone Natural products CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 235000021021 grapes Nutrition 0.000 description 1
- 229910052602 gypsum Inorganic materials 0.000 description 1
- 239000010440 gypsum Substances 0.000 description 1
- 210000002837 heart atrium Anatomy 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- ONUFESLQCSAYKA-UHFFFAOYSA-N iprodione Chemical compound O=C1N(C(=O)NC(C)C)CC(=O)N1C1=CC(Cl)=CC(Cl)=C1 ONUFESLQCSAYKA-UHFFFAOYSA-N 0.000 description 1
- 239000003350 kerosene Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- LCGLNKUTAGEVQW-UHFFFAOYSA-N methyl monoether Natural products COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 235000021017 pears Nutrition 0.000 description 1
- VSIIXMUUUJUKCM-UHFFFAOYSA-D pentacalcium;fluoride;triphosphate Chemical compound [F-].[Ca+2].[Ca+2].[Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O VSIIXMUUUJUKCM-UHFFFAOYSA-D 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 230000008654 plant damage Effects 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 229910052903 pyrophyllite Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000009331 sowing Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- FDDDEECHVMSUSB-UHFFFAOYSA-N sulfanilamide Chemical compound NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 239000010455 vermiculite Substances 0.000 description 1
- 229910052902 vermiculite Inorganic materials 0.000 description 1
- 235000019354 vermiculite Nutrition 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- 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
-
- 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
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)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pyrrole Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP975278A JPS54103865A (en) | 1978-01-31 | 1978-01-31 | Pyrrole derivative and agricultural and horticultural fungicides |
| JP8147578A JPS559031A (en) | 1978-07-06 | 1978-07-06 | Pyrrole-type agricultural and horticultural fungicide |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH639372A5 true CH639372A5 (de) | 1983-11-15 |
Family
ID=26344535
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH52479A CH639372A5 (de) | 1978-01-31 | 1979-01-18 | Aromatisch substituierte pyrrolderivate, verfahren zu deren herstellung, diese enthaltende fungizide zusammensetzungen und verfahren zur bekaempfung von pilzen. |
Country Status (15)
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ATE40114T1 (de) * | 1981-12-18 | 1989-02-15 | Ciba Geigy Ag | Mikrobizide sulfenyl-pyrrole. |
| PT78722A (en) * | 1983-06-17 | 1984-07-01 | Ciba Geigy Ag | Process for preparing novel n-alkylated 3-phenyl-4-cianopyrrole derivatives |
| US4546099A (en) * | 1983-07-22 | 1985-10-08 | Ciba-Geigy Corporation | N-Aminomethyl-3-phenyl-4-cyanopyrrole derivatives, compositions and use thereof as microbicides |
| GB2268735B (en) * | 1992-07-17 | 1996-02-28 | Xerox Corp | Sheet feeding apparatus |
-
1978
- 1978-12-18 IL IL56243A patent/IL56243A/xx unknown
-
1979
- 1979-01-03 ES ES476565A patent/ES476565A1/es not_active Expired
- 1979-01-10 FR FR7900534A patent/FR2416223A1/fr active Granted
- 1979-01-11 GB GB7901062A patent/GB2013187B/en not_active Expired
- 1979-01-15 NZ NZ189386A patent/NZ189386A/xx unknown
- 1979-01-15 NL NL7900303A patent/NL7900303A/xx not_active Application Discontinuation
- 1979-01-18 CH CH52479A patent/CH639372A5/de not_active IP Right Cessation
- 1979-01-19 HU HU79NI222A patent/HU182546B/hu not_active IP Right Cessation
- 1979-01-25 IT IT47772/79A patent/IT1115134B/it active
- 1979-01-26 AR AR275320A patent/AR218102A1/es active
- 1979-01-29 PL PL1979213084A patent/PL116907B1/pl unknown
- 1979-01-30 BE BE193150A patent/BE873799A/xx not_active IP Right Cessation
- 1979-01-30 BR BR7900567A patent/BR7900567A/pt unknown
- 1979-01-30 DE DE2903458A patent/DE2903458C3/de not_active Expired
- 1979-12-18 AU AU42655/78A patent/AU507733B2/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| AU4265578A (en) | 1979-08-30 |
| IL56243A0 (en) | 1979-03-12 |
| FR2416223B1 (enrdf_load_stackoverflow) | 1982-05-28 |
| ES476565A1 (es) | 1979-12-16 |
| IT1115134B (it) | 1986-02-03 |
| IL56243A (en) | 1982-07-30 |
| GB2013187B (en) | 1982-06-03 |
| AR218102A1 (es) | 1980-05-15 |
| AU507733B2 (en) | 1980-02-28 |
| BR7900567A (pt) | 1979-08-28 |
| DE2903458A1 (de) | 1979-08-02 |
| HU182546B (en) | 1984-02-28 |
| IT7947772A0 (it) | 1979-01-25 |
| BE873799A (fr) | 1979-05-16 |
| PL213084A1 (enrdf_load_stackoverflow) | 1980-02-11 |
| FR2416223A1 (fr) | 1979-08-31 |
| GB2013187A (en) | 1979-08-08 |
| DE2903458C3 (de) | 1980-10-23 |
| NL7900303A (nl) | 1979-08-02 |
| NZ189386A (en) | 1980-08-26 |
| PL116907B1 (en) | 1981-07-31 |
| DE2903458B2 (de) | 1980-02-28 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased | ||
| PL | Patent ceased |