DD297959A5 - N-vinyl-3-cyano-4-phenyl-pyrrol-derivate - Google Patents

N-vinyl-3-cyano-4-phenyl-pyrrol-derivate Download PDF

Info

Publication number: DD297959A5
Authority: DD; German Democratic Republic
Prior art keywords: carbon atoms; hydrogen; alkyl; straight; chain
Prior art date: 1989-07-05

Application number

DD90342470A

Other languages

German (de)

English (en)

Inventor

Ulrich Heinemann

Detlef Wollweber

Wilhelm Brandes

Stefan Dutzmann

Gerd Haenssler

Original Assignee

��@��k��

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1989-07-05

Filing date

1990-07-03

Publication date

1992-01-30

1990-07-03 Application filed by ��@��k�� filed Critical ��@��k��

1992-01-30 Publication of DD297959A5 publication Critical patent/DD297959A5/de

Links

XWYQPDOOJJKHDJ-UHFFFAOYSA-N 1-ethenyl-4-phenylpyrrole-3-carbonitrile Chemical class C=CN1C=C(C#N)C(C=2C=CC=CC=2)=C1 XWYQPDOOJJKHDJ-UHFFFAOYSA-N 0.000 title claims abstract description 12
238000002360 preparation method Methods 0.000 claims abstract description 20
238000000034 method Methods 0.000 claims abstract description 15
BMMCNKYHQAKJBN-UHFFFAOYSA-N 4-phenyl-1h-pyrrole-3-carbonitrile Chemical class N#CC1=CNC=C1C1=CC=CC=C1 BMMCNKYHQAKJBN-UHFFFAOYSA-N 0.000 claims abstract description 8
241000607479 Yersinia pestis Species 0.000 claims abstract description 8
VXAWCKIQYKXJMD-UHFFFAOYSA-N ethynamine Chemical group NC#C VXAWCKIQYKXJMD-UHFFFAOYSA-N 0.000 claims abstract description 6
125000004432 carbon atom Chemical group C* 0.000 claims description 54
239000000460 chlorine Substances 0.000 claims description 47
-1 methylenedioxy Chemical class 0.000 claims description 45
125000000217 alkyl group Chemical group 0.000 claims description 35
229910052739 hydrogen Inorganic materials 0.000 claims description 30
239000001257 hydrogen Substances 0.000 claims description 30
125000005843 halogen group Chemical group 0.000 claims description 28
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 23
229910052731 fluorine Inorganic materials 0.000 claims description 23
239000011737 fluorine Substances 0.000 claims description 23
229910052736 halogen Inorganic materials 0.000 claims description 22
150000002367 halogens Chemical class 0.000 claims description 22
125000004438 haloalkoxy group Chemical group 0.000 claims description 20
125000001188 haloalkyl group Chemical group 0.000 claims description 20
150000002431 hydrogen Chemical class 0.000 claims description 20
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 19
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 19
125000003545 alkoxy group Chemical group 0.000 claims description 16
125000004414 alkyl thio group Chemical group 0.000 claims description 12
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 9
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
229910052801 chlorine Inorganic materials 0.000 claims description 9
125000001309 chloro group Chemical group Cl* 0.000 claims description 8
229910052757 nitrogen Inorganic materials 0.000 claims description 8
125000004433 nitrogen atom Chemical group N* 0.000 claims description 8
UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 claims description 8
229920006395 saturated elastomer Polymers 0.000 claims description 8
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 7
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 6
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 6
229910052794 bromium Inorganic materials 0.000 claims description 6
125000004995 haloalkylthio group Chemical group 0.000 claims description 6
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 5
239000004606 Fillers/Extenders Substances 0.000 claims description 4
125000005530 alkylenedioxy group Chemical class 0.000 claims description 4
239000003795 chemical substances by application Substances 0.000 claims description 3
239000003085 diluting agent Substances 0.000 claims description 3
238000002156 mixing Methods 0.000 claims description 2
239000004094 surface-active agent Substances 0.000 claims description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
229910052799 carbon Inorganic materials 0.000 claims 1
239000000575 pesticide Substances 0.000 claims 1
150000008060 phenylpyrroles Chemical class 0.000 claims 1
239000000126 substance Substances 0.000 abstract description 3
150000001875 compounds Chemical class 0.000 description 35
241000196324 Embryophyta Species 0.000 description 17
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 16
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
239000002904 solvent Substances 0.000 description 12
239000003995 emulsifying agent Substances 0.000 description 10
239000000203 mixture Substances 0.000 description 10
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
239000004480 active ingredient Substances 0.000 description 8
230000001681 protective effect Effects 0.000 description 8
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 7
238000009472 formulation Methods 0.000 description 7
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
125000001424 substituent group Chemical group 0.000 description 6
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
125000002877 alkyl aryl group Chemical group 0.000 description 5
201000010099 disease Diseases 0.000 description 5
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 5
239000008187 granular material Substances 0.000 description 5
239000003921 oil Substances 0.000 description 5
235000019198 oils Nutrition 0.000 description 5
229920000151 polyglycol Polymers 0.000 description 5
239000010695 polyglycol Substances 0.000 description 5
150000003254 radicals Chemical class 0.000 description 5
238000005507 spraying Methods 0.000 description 5
240000007594 Oryza sativa Species 0.000 description 4
241000228453 Pyrenophora Species 0.000 description 4
239000000969 carrier Substances 0.000 description 4
239000012141 concentrate Substances 0.000 description 4
239000003814 drug Substances 0.000 description 4
229940079593 drug Drugs 0.000 description 4
238000011081 inoculation Methods 0.000 description 4
239000007858 starting material Substances 0.000 description 4
239000000725 suspension Substances 0.000 description 4
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
241000123650 Botrytis cinerea Species 0.000 description 3
240000005979 Hordeum vulgare Species 0.000 description 3
235000007340 Hordeum vulgare Nutrition 0.000 description 3
235000007164 Oryza sativa Nutrition 0.000 description 3
238000006243 chemical reaction Methods 0.000 description 3
150000002170 ethers Chemical class 0.000 description 3
238000011156 evaluation Methods 0.000 description 3
230000000855 fungicidal effect Effects 0.000 description 3
239000000417 fungicide Substances 0.000 description 3
229910052500 inorganic mineral Inorganic materials 0.000 description 3
239000007788 liquid Substances 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
239000000843 powder Substances 0.000 description 3
235000009566 rice Nutrition 0.000 description 3
VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
239000007787 solid Substances 0.000 description 3
GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 description 2
241001480061 Blumeria graminis Species 0.000 description 2
241001465180 Botrytis Species 0.000 description 2
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
101150065749 Churc1 gene Proteins 0.000 description 2
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
241000221787 Erysiphe Species 0.000 description 2
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
241000223218 Fusarium Species 0.000 description 2
206010061217 Infestation Diseases 0.000 description 2
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical class [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 2
241000228456 Leptosphaeria Species 0.000 description 2
241001330975 Magnaporthe oryzae Species 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
241000736122 Parastagonospora nodorum Species 0.000 description 2
ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
102100038239 Protein Churchill Human genes 0.000 description 2
241000520648 Pyrenophora teres Species 0.000 description 2
241000231139 Pyricularia Species 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
239000013543 active substance Substances 0.000 description 2
150000001338 aliphatic hydrocarbons Chemical class 0.000 description 2
AAMATCKFMHVIDO-UHFFFAOYSA-N azane;1h-pyrrole Chemical compound N.C=1C=CNC=1 AAMATCKFMHVIDO-UHFFFAOYSA-N 0.000 description 2
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
239000002270 dispersing agent Substances 0.000 description 2
239000000975 dye Substances 0.000 description 2
XTHFKEDIFFGKHM-UHFFFAOYSA-N ethylene glycol dimethyl ether Natural products COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
239000006260 foam Substances 0.000 description 2
150000008282 halocarbons Chemical class 0.000 description 2
239000011707 mineral Substances 0.000 description 2
239000003960 organic solvent Substances 0.000 description 2
244000052769 pathogen Species 0.000 description 2
239000003208 petroleum Substances 0.000 description 2
239000002689 soil Substances 0.000 description 2
241000894007 species Species 0.000 description 2
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
239000008096 xylene Substances 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
KAESVJOAVNADME-UHFFFAOYSA-N 1H-pyrrole Natural products C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 1
125000004715 3-methylbutylthio group Chemical group CC(CCS*)C 0.000 description 1
HVKQQHNYUJYTFB-UHFFFAOYSA-N 4-(2,3-dichlorophenyl)-1-ethenylpyrrole-3-carbonitrile Chemical compound ClC1=CC=CC(C=2C(=CN(C=C)C=2)C#N)=C1Cl HVKQQHNYUJYTFB-UHFFFAOYSA-N 0.000 description 1
OCZRHTFVCLAJGC-UHFFFAOYSA-N 4-(3-chloro-2-fluorophenyl)-1-[1-(diethylamino)prop-1-enyl]pyrrole-3-carbonitrile Chemical compound CCN(CC)C(=CC)N1C=C(C#N)C(C=2C(=C(Cl)C=CC=2)F)=C1 OCZRHTFVCLAJGC-UHFFFAOYSA-N 0.000 description 1
AFTOVYFNPMUYNW-UHFFFAOYSA-N 4-(3-chloro-2-fluorophenyl)-1h-pyrrole-3-carbonitrile Chemical compound FC1=C(Cl)C=CC=C1C1=CNC=C1C#N AFTOVYFNPMUYNW-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
244000215068 Acacia senegal Species 0.000 description 1
229920001817 Agar Polymers 0.000 description 1
RGCKGOZRHPZPFP-UHFFFAOYSA-N Alizarin Natural products C1=CC=C2C(=O)C3=C(O)C(O)=CC=C3C(=O)C2=C1 RGCKGOZRHPZPFP-UHFFFAOYSA-N 0.000 description 1
241000223600 Alternaria Species 0.000 description 1
241001149961 Alternaria brassicae Species 0.000 description 1
241000235349 Ascomycota Species 0.000 description 1
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
241000221198 Basidiomycota Species 0.000 description 1
241000190150 Bipolaris sorokiniana Species 0.000 description 1
241000895523 Blumeria graminis f. sp. hordei Species 0.000 description 1
ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
229910021532 Calcite Inorganic materials 0.000 description 1
229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
241001157813 Cercospora Species 0.000 description 1
241000906476 Cercospora canescens Species 0.000 description 1
241000760356 Chytridiomycetes Species 0.000 description 1
241000228437 Cochliobolus Species 0.000 description 1
244000060011 Cocos nucifera Species 0.000 description 1
235000013162 Cocos nucifera Nutrition 0.000 description 1
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
241000371644 Curvularia ravenelii Species 0.000 description 1
241000233866 Fungi Species 0.000 description 1
241000223194 Fusarium culmorum Species 0.000 description 1
229920000084 Gum arabic Polymers 0.000 description 1
239000005909 Kieselgur Substances 0.000 description 1
241000228457 Leptosphaeria maculans Species 0.000 description 1
241000251953 Leucotrichia Species 0.000 description 1
241001300479 Macroptilium Species 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
ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 1
208000031888 Mycoses Diseases 0.000 description 1
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
244000061176 Nicotiana tabacum Species 0.000 description 1
235000002637 Nicotiana tabacum Nutrition 0.000 description 1
241001668536 Oculimacula yallundae Species 0.000 description 1
241000233654 Oomycetes Species 0.000 description 1
241001223281 Peronospora Species 0.000 description 1
241000201565 Peronospora viciae f. sp. pisi Species 0.000 description 1
244000046052 Phaseolus vulgaris Species 0.000 description 1
235000010627 Phaseolus vulgaris Nutrition 0.000 description 1
241000233614 Phytophthora Species 0.000 description 1
241000233622 Phytophthora infestans Species 0.000 description 1
241001503460 Plasmodiophorida Species 0.000 description 1
241000233626 Plasmopara Species 0.000 description 1
241001281803 Plasmopara viticola Species 0.000 description 1
241000317981 Podosphaera fuliginea Species 0.000 description 1
229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
239000004372 Polyvinyl alcohol Substances 0.000 description 1
108010009736 Protein Hydrolysates Proteins 0.000 description 1
241000682843 Pseudocercosporella Species 0.000 description 1
241001281802 Pseudoperonospora Species 0.000 description 1
241001281805 Pseudoperonospora cubensis Species 0.000 description 1
241000342307 Pseudoperonospora humuli Species 0.000 description 1
241000221300 Puccinia Species 0.000 description 1
241001123569 Puccinia recondita Species 0.000 description 1
241000228454 Pyrenophora graminea Species 0.000 description 1
241000233639 Pythium Species 0.000 description 1
241000918584 Pythium ultimum Species 0.000 description 1
206010037888 Rash pustular Diseases 0.000 description 1
239000004113 Sepiolite Substances 0.000 description 1
241001533598 Septoria Species 0.000 description 1
241000579741 Sphaerotheca <fungi> Species 0.000 description 1
241001617088 Thanatephorus sasakii Species 0.000 description 1
241000722133 Tilletia Species 0.000 description 1
241000722093 Tilletia caries Species 0.000 description 1
GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 1
241000221576 Uromyces Species 0.000 description 1
241000221577 Uromyces appendiculatus Species 0.000 description 1
241000221566 Ustilago Species 0.000 description 1
241000514371 Ustilago avenae Species 0.000 description 1
241000007070 Ustilago nuda Species 0.000 description 1
241000317942 Venturia <ichneumonid wasp> Species 0.000 description 1
241000228452 Venturia inaequalis Species 0.000 description 1
BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical class ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
240000008042 Zea mays Species 0.000 description 1
235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
235000002017 Zea mays subsp mays Nutrition 0.000 description 1
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
239000000205 acacia gum Substances 0.000 description 1
235000010489 acacia gum Nutrition 0.000 description 1
230000000895 acaricidal effect Effects 0.000 description 1
239000000642 acaricide Substances 0.000 description 1
239000000654 additive Substances 0.000 description 1
239000000853 adhesive Substances 0.000 description 1
230000001070 adhesive effect Effects 0.000 description 1
239000000443 aerosol Substances 0.000 description 1
239000008272 agar Substances 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
125000002723 alicyclic group Chemical group 0.000 description 1
125000001931 aliphatic group Chemical group 0.000 description 1
HFVAFDPGUJEFBQ-UHFFFAOYSA-M alizarin red S Chemical compound [Na+].O=C1C2=CC=CC=C2C(=O)C2=C1C=C(S([O-])(=O)=O)C(O)=C2O HFVAFDPGUJEFBQ-UHFFFAOYSA-M 0.000 description 1
229940045714 alkyl sulfonate alkylating agent Drugs 0.000 description 1
150000008052 alkyl sulfonates Chemical class 0.000 description 1
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
235000012211 aluminium silicate Nutrition 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
125000000129 anionic group Chemical group 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
125000005228 aryl sulfonate group Chemical group 0.000 description 1
229960000892 attapulgite Drugs 0.000 description 1
229910052796 boron Inorganic materials 0.000 description 1
125000005998 bromoethyl group Chemical group 0.000 description 1
125000005997 bromomethyl group Chemical group 0.000 description 1
230000001680 brushing effect Effects 0.000 description 1
239000001273 butane Substances 0.000 description 1
229910002092 carbon dioxide Inorganic materials 0.000 description 1
239000001569 carbon dioxide Substances 0.000 description 1
239000001768 carboxy methyl cellulose Substances 0.000 description 1
235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
239000008112 carboxymethyl-cellulose Substances 0.000 description 1
235000013339 cereals Nutrition 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
150000008422 chlorobenzenes Chemical class 0.000 description 1
229920005556 chlorobutyl Polymers 0.000 description 1
125000004775 chlorodifluoromethyl group Chemical group FC(F)(Cl)* 0.000 description 1
125000002603 chloroethyl group Chemical group [H]C([*])([H])C([H])([H])Cl 0.000 description 1
125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 1
239000008199 coating composition Substances 0.000 description 1
239000010941 cobalt Substances 0.000 description 1
229910017052 cobalt Inorganic materials 0.000 description 1
GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
229910052802 copper Inorganic materials 0.000 description 1
239000010949 copper Substances 0.000 description 1
235000005822 corn Nutrition 0.000 description 1
GUJOJGAPFQRJSV-UHFFFAOYSA-N dialuminum;dioxosilane;oxygen(2-);hydrate Chemical compound O.[O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O GUJOJGAPFQRJSV-UHFFFAOYSA-N 0.000 description 1
125000004772 dichloromethyl group Chemical group [H]C(Cl)(Cl)* 0.000 description 1
235000014113 dietary fatty acids Nutrition 0.000 description 1
125000006001 difluoroethyl group Chemical group 0.000 description 1
125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 description 1
231100000676 disease causative agent Toxicity 0.000 description 1
239000010459 dolomite Substances 0.000 description 1
229910000514 dolomite Inorganic materials 0.000 description 1
238000001035 drying Methods 0.000 description 1
238000010410 dusting Methods 0.000 description 1
230000000694 effects Effects 0.000 description 1
230000001804 emulsifying effect Effects 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
238000005538 encapsulation Methods 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
239000000194 fatty acid Substances 0.000 description 1
229930195729 fatty acid Natural products 0.000 description 1
239000003337 fertilizer Substances 0.000 description 1
235000013312 flour Nutrition 0.000 description 1
MUJOIMFVNIBMKC-UHFFFAOYSA-N fludioxonil Chemical compound C=12OC(F)(F)OC2=CC=CC=1C1=CNC=C1C#N MUJOIMFVNIBMKC-UHFFFAOYSA-N 0.000 description 1
125000005817 fluorobutyl group Chemical group [H]C([H])(F)C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000003784 fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 description 1
125000004785 fluoromethoxy group Chemical group [H]C([H])(F)O* 0.000 description 1
125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 description 1
238000005187 foaming Methods 0.000 description 1
235000012055 fruits and vegetables Nutrition 0.000 description 1
229910021485 fumed silica Inorganic materials 0.000 description 1
239000007789 gas Substances 0.000 description 1
239000003630 growth substance Substances 0.000 description 1
239000004009 herbicide Substances 0.000 description 1
GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
238000000338 in vitro Methods 0.000 description 1
238000011534 incubation Methods 0.000 description 1
239000001023 inorganic pigment Substances 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
229910052742 iron Inorganic materials 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
238000002955 isolation Methods 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
239000004816 latex Substances 0.000 description 1
229920000126 latex Polymers 0.000 description 1
239000000787 lecithin Substances 0.000 description 1
235000010445 lecithin Nutrition 0.000 description 1
WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical class [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
239000004579 marble Substances 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
229920000609 methyl cellulose Polymers 0.000 description 1
239000001923 methylcellulose Substances 0.000 description 1
239000002480 mineral oil Substances 0.000 description 1
239000003595 mist Substances 0.000 description 1
239000011733 molybdenum Substances 0.000 description 1
229910052750 molybdenum Inorganic materials 0.000 description 1
229910052901 montmorillonite Inorganic materials 0.000 description 1
RJSCZBRDRBIRHP-UHFFFAOYSA-N n,n-diethylprop-1-yn-1-amine Chemical compound CCN(CC)C#CC RJSCZBRDRBIRHP-UHFFFAOYSA-N 0.000 description 1
IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
JIKUXBYRTXDNIY-UHFFFAOYSA-N n-methyl-n-phenylformamide Chemical compound O=CN(C)C1=CC=CC=C1 JIKUXBYRTXDNIY-UHFFFAOYSA-N 0.000 description 1
OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
229940042880 natural phospholipid Drugs 0.000 description 1
JCXJVPUVTGWSNB-UHFFFAOYSA-N nitrogen dioxide Inorganic materials O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 description 1
235000015097 nutrients Nutrition 0.000 description 1
239000011368 organic material Substances 0.000 description 1
229910052625 palygorskite Inorganic materials 0.000 description 1
239000006072 paste Substances 0.000 description 1
230000001717 pathogenic effect Effects 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
150000003904 phospholipids Chemical class 0.000 description 1
230000003032 phytopathogenic effect Effects 0.000 description 1
239000002798 polar solvent Substances 0.000 description 1
229920000642 polymer Polymers 0.000 description 1
239000011118 polyvinyl acetate Substances 0.000 description 1
229920002689 polyvinyl acetate Polymers 0.000 description 1
229920002451 polyvinyl alcohol Polymers 0.000 description 1
239000000047 product Substances 0.000 description 1
239000001294 propane Substances 0.000 description 1
239000003380 propellant Substances 0.000 description 1
239000011814 protection agent Substances 0.000 description 1
239000003531 protein hydrolysate Substances 0.000 description 1
239000008262 pumice Substances 0.000 description 1
208000029561 pustule Diseases 0.000 description 1
239000010453 quartz Substances 0.000 description 1
239000011435 rock Substances 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
229910052624 sepiolite Inorganic materials 0.000 description 1
235000019355 sepiolite Nutrition 0.000 description 1
150000004760 silicates Chemical class 0.000 description 1
239000000243 solution Substances 0.000 description 1
239000007921 spray Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 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
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
125000006000 trichloroethyl group Chemical group 0.000 description 1
125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 1
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
238000010626 work up procedure Methods 0.000 description 1
239000011701 zinc Substances 0.000 description 1
229910052725 zinc Inorganic materials 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
- C07D207/32—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 only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D207/325—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 only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms with substituted hydrocarbon radicals directly attached to the ring nitrogen atom
- C07D207/327—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile 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
- A01N43/36—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

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
Agronomy & Crop Science (AREA)
Pest Control & Pesticides (AREA)
Plant Pathology (AREA)
Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Dentistry (AREA)
General Health & Medical Sciences (AREA)
Wood Science & Technology (AREA)
Zoology (AREA)
Environmental Sciences (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Plural Heterocyclic Compounds (AREA)
Pyrrole Compounds (AREA)

DD90342470A 1989-07-05 1990-07-03 N-vinyl-3-cyano-4-phenyl-pyrrol-derivate DD297959A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE3922104A DE3922104A1 (de)	1989-07-05	1989-07-05	N-vinyl-3-cyano-4-phenyl-pyrrol-derivate

Publications (1)

Publication Number	Publication Date
DD297959A5 true DD297959A5 (de)	1992-01-30

Family

ID=6384357

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD90342470A DD297959A5 (de)	1989-07-05	1990-07-03	N-vinyl-3-cyano-4-phenyl-pyrrol-derivate

Country Status (7)

Country	Link
US (1)	US5061312A (ja)
EP (1)	EP0407790A1 (ja)
JP (1)	JPH0344368A (ja)
KR (1)	KR910002793A (ja)
BR (1)	BR9003189A (ja)
DD (1)	DD297959A5 (ja)
DE (1)	DE3922104A1 (ja)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5130328A (en) *	1991-09-06	1992-07-14	American Cyanamid Company	N-alkanoylaminomethyl and N-aroylaminomethyl pyrrole insecticidal and acaricidal agents

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
BG43855A3 (bg) *	1983-06-17	1988-08-15	Ciba - Geigy Ag	Фунгицидно средство и метод за борба срещу фитопатогенни гъбички
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
US4705800A (en) *	1985-06-21	1987-11-10	Ciba-Geigy Corporation	Difluorbenzodioxyl cyanopyrrole microbicidal compositions
ES2022443B3 (es) *	1986-03-04	1991-12-01	Ciba-Geigy Ag	Utilizacion fungicida de un derivado de cianopirrol.
DE3702852A1 (de) *	1987-01-31	1988-08-11	Bayer Ag	1-aminomethyl-3-aryl-4-cyano-pyrrole
DE3718375A1 (de) *	1987-06-02	1988-12-15	Bayer Ag	Verfahren zur herstellung von 3-cyano-4-aryl-pyrrolen
EP0310558A3 (de) *	1987-10-02	1990-07-04	Ciba-Geigy Ag	Mikrobizide Mittel

1989
- 1989-07-05 DE DE3922104A patent/DE3922104A1/de not_active Withdrawn
1990
- 1990-06-18 US US07/539,631 patent/US5061312A/en not_active Expired - Fee Related
- 1990-06-23 EP EP90111937A patent/EP0407790A1/de not_active Withdrawn
- 1990-06-29 JP JP2170333A patent/JPH0344368A/ja active Pending
- 1990-07-03 DD DD90342470A patent/DD297959A5/de not_active IP Right Cessation
- 1990-07-04 KR KR1019900010048A patent/KR910002793A/ko not_active Withdrawn
- 1990-07-05 BR BR909003189A patent/BR9003189A/pt unknown

Also Published As

Publication number	Publication date
EP0407790A1 (de)	1991-01-16
KR910002793A (ko)	1991-02-26
BR9003189A (pt)	1991-08-27
US5061312A (en)	1991-10-29
DE3922104A1 (de)	1991-01-17
JPH0344368A (ja)	1991-02-26

Legal Events

Date	Code	Title	Description
2000-03-30	ENJ	Ceased due to non-payment of renewal fee

Publication	Publication Date	Title
EP0628540B1 (de)	1999-01-20	2-Oximino-2-phenyl-acetamide
DE3835576A1 (de)	1989-10-12	3,7-disubstituierte benzthiazolone
EP0277537B1 (de)	1990-09-26	1-Aminomethyl-3-aryl-4-cyano-pyrrole
DE4233198A1 (de)	1994-04-07	Substituierte Thiophencarbonsäureamide
EP0438717A2 (de)	1991-07-31	Trisubstituierte 1,2,4-Triazin-3,5-dione und neue Zwischenprodukte
DE4004035A1 (de)	1991-06-27	Substituierte 1-aminomethyl-3-aryl-4-cyano-pyrrole
EP0557860B1 (de)	2001-01-10	Substituierte Pyridylpyrimidine und ihre Verwendung als Schädlingsbekämpfungsmittel
DE4318916A1 (de)	1994-12-08	Cyclobutylazole
DD297959A5 (de)	1992-01-30	N-vinyl-3-cyano-4-phenyl-pyrrol-derivate
DE3708320A1 (de)	1988-09-22	Benzaldoxim-derivate
DD248953A5 (de)	1987-08-26	Schaedlingsbekaempfungsmittel
EP0422461A2 (de)	1991-04-17	Trisubstituierte 1,3,5-Triazin-2,4,6-trione
EP0529400A1 (de)	1993-03-03	3-(2-Chlor-3-trifluormethylphenyl)-4-cyanopyrrol, als Schädlungsbekämpfungsmittel
EP0185983A1 (de)	1986-07-02	N-(3-Chlor-1,2,4-oxadiazol-5-yl)-harnstoffe
EP0391188A1 (de)	1990-10-10	Fungizide Mittel auf Basis von teilweise bekannten nitrosubstituierten Benzthiazolonen, neue nitrosubstituierte Benzthiazolone und Verfahren zu ihrer Herstellung
DE3607624A1 (de)	1987-09-10	N-thioxosubstituierte jodpropargylurethane
EP0208110A1 (de)	1987-01-14	Fungizide Mittel auf Benzaldoxim-Derivat-Basis
DE3716023A1 (de)	1988-12-08	Azolyl-tetrahydrofuran-2-yliden-methane
DE3639900A1 (de)	1988-05-26	Saccharin-salze von substituierten aminen
DE4208874A1 (de)	1993-09-23	Fungizide mittel auf basis von aminosubstituierten chinolinchinonen
EP0224140A1 (de)	1987-06-03	Thienylharnstoff-Derivate
EP0281909A2 (de)	1988-09-14	Benzaldoxim-carbamat-Derivate
DE3831914A1 (de)	1990-03-22	Schaedlingsbekaempfungsmittel auf basis von teilweise neuen 2-aryl-substituierten 1,10-phenanthrolinen und deren herstellung
DE3742970A1 (de)	1989-06-29	Substituierte pyrimidine
DE4227073A1 (de)	1994-02-24	Pyridylsubstituierte 1,3-Oxazolidin-Derivate