DE2410184A1 - Chinonoxim-acylhydrazon-derivate, verfahren zu ihrer herstellung, sowie ihre verwendung als fungizide - Google Patents
Chinonoxim-acylhydrazon-derivate, verfahren zu ihrer herstellung, sowie ihre verwendung als fungizideInfo
- Publication number
- DE2410184A1 DE2410184A1 DE2410184A DE2410184A DE2410184A1 DE 2410184 A1 DE2410184 A1 DE 2410184A1 DE 2410184 A DE2410184 A DE 2410184A DE 2410184 A DE2410184 A DE 2410184A DE 2410184 A1 DE2410184 A1 DE 2410184A1
- Authority
- DE
- Germany
- Prior art keywords
- acid hydrazide
- stands
- quinone
- acylhydrazone
- oxime
- Prior art date
- Legal status (The legal status 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 status listed.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 10
- 239000000417 fungicide Substances 0.000 title claims description 7
- 238000004519 manufacturing process Methods 0.000 title description 3
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 claims description 13
- JSTCPNFNKICNNO-UHFFFAOYSA-N 4-nitrosophenol Chemical compound OC1=CC=C(N=O)C=C1 JSTCPNFNKICNNO-UHFFFAOYSA-N 0.000 claims description 13
- 241000233866 Fungi Species 0.000 claims description 11
- 239000002253 acid Substances 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 239000004606 Fillers/Extenders Substances 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 235000001674 Agaricus brunnescens Nutrition 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 239000003085 diluting agent Substances 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical group 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 2
- 239000011707 mineral Substances 0.000 claims description 2
- 125000001624 naphthyl group Chemical group 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 239000011593 sulfur Substances 0.000 claims description 2
- 239000004094 surface-active agent Substances 0.000 claims description 2
- 150000002431 hydrogen Chemical group 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 description 23
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 239000000460 chlorine Substances 0.000 description 9
- -1 hydroxy, Methyl Chemical group 0.000 description 9
- 239000000203 mixture Substances 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 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 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 5
- 241000196324 Embryophyta Species 0.000 description 5
- 241000223218 Fusarium Species 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 206010061217 Infestation Diseases 0.000 description 4
- 238000009472 formulation Methods 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 239000000969 carrier Substances 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 201000010099 disease Diseases 0.000 description 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 3
- 239000002270 dispersing agent Substances 0.000 description 3
- 239000008187 granular material Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000002689 soil Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 230000009885 systemic effect Effects 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
- LOUPRKONTZGTKE-WZBLMQSHSA-N Quinine Chemical compound C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@@H]2[C@H](O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-WZBLMQSHSA-N 0.000 description 2
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000003995 emulsifying agent Substances 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 230000000855 fungicidal effect Effects 0.000 description 2
- 230000002464 fungitoxic effect Effects 0.000 description 2
- 229940042795 hydrazides for tuberculosis treatment Drugs 0.000 description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000006072 paste Substances 0.000 description 2
- 229920000151 polyglycol Polymers 0.000 description 2
- 239000010695 polyglycol Substances 0.000 description 2
- 239000011435 rock Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000005507 spraying Methods 0.000 description 2
- AIDYKFYCUUWCBS-UHFFFAOYSA-N 1-(2-methylbut-3-yn-2-yl)-3-phenylurea Chemical compound C#CC(C)(C)NC(=O)NC1=CC=CC=C1 AIDYKFYCUUWCBS-UHFFFAOYSA-N 0.000 description 1
- VQKAUKMRXXSHLT-UHFFFAOYSA-N 2-(2,4,6-trichlorophenoxy)acetohydrazide Chemical compound NNC(=O)COC1=C(Cl)C=C(Cl)C=C1Cl VQKAUKMRXXSHLT-UHFFFAOYSA-N 0.000 description 1
- KDXDKFKXGCNKRP-UHFFFAOYSA-N 2-(2,4-dichloro-5-methylphenyl)sulfanylacetohydrazide Chemical compound CC1=CC(SCC(=O)NN)=C(Cl)C=C1Cl KDXDKFKXGCNKRP-UHFFFAOYSA-N 0.000 description 1
- OEYOIIKYUVBUJN-UHFFFAOYSA-N 2-(2,4-dichlorophenoxy)acetohydrazide Chemical compound NNC(=O)COC1=CC=C(Cl)C=C1Cl OEYOIIKYUVBUJN-UHFFFAOYSA-N 0.000 description 1
- ZCOGPWLKTSAHHZ-UHFFFAOYSA-N 2-(2,4-dinitrophenyl)sulfanylacetohydrazide Chemical compound NNC(=O)CSC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O ZCOGPWLKTSAHHZ-UHFFFAOYSA-N 0.000 description 1
- RMYVUBLHPGYXEC-UHFFFAOYSA-N 2-(2-chloro-4-methylphenoxy)acetohydrazide Chemical compound CC1=CC=C(OCC(=O)NN)C(Cl)=C1 RMYVUBLHPGYXEC-UHFFFAOYSA-N 0.000 description 1
- NGRIRZVRAOAVPJ-UHFFFAOYSA-N 2-(2-chloro-4-methylphenyl)sulfanylacetohydrazide Chemical compound CC1=CC=C(SCC(=O)NN)C(Cl)=C1 NGRIRZVRAOAVPJ-UHFFFAOYSA-N 0.000 description 1
- DSVNKLUHRGOPJC-UHFFFAOYSA-N 2-(2-chlorophenoxy)acetohydrazide Chemical compound NNC(=O)COC1=CC=CC=C1Cl DSVNKLUHRGOPJC-UHFFFAOYSA-N 0.000 description 1
- CMDKLIHXWQMSCZ-UHFFFAOYSA-N 2-(2-ethylphenyl)sulfanylacetohydrazide Chemical compound CCC1=CC=CC=C1SCC(=O)NN CMDKLIHXWQMSCZ-UHFFFAOYSA-N 0.000 description 1
- WGQDMRNLIVOSOW-UHFFFAOYSA-N 2-(2-methoxyphenoxy)acetohydrazide Chemical compound COC1=CC=CC=C1OCC(=O)NN WGQDMRNLIVOSOW-UHFFFAOYSA-N 0.000 description 1
- SQBJZXMIULOBEK-UHFFFAOYSA-N 2-(2-methoxyphenyl)sulfanylacetohydrazide Chemical compound COC1=CC=CC=C1SCC(=O)NN SQBJZXMIULOBEK-UHFFFAOYSA-N 0.000 description 1
- JJMFQNRAJMARBA-UHFFFAOYSA-N 2-(2-methyl-4-nitrophenyl)sulfanylacetohydrazide Chemical compound CC1=CC([N+]([O-])=O)=CC=C1SCC(=O)NN JJMFQNRAJMARBA-UHFFFAOYSA-N 0.000 description 1
- ZCKNJFQLMUSOAJ-UHFFFAOYSA-N 2-(2-methylphenoxy)acetohydrazide Chemical compound CC1=CC=CC=C1OCC(=O)NN ZCKNJFQLMUSOAJ-UHFFFAOYSA-N 0.000 description 1
- QUTJSDSZEWQPSX-UHFFFAOYSA-N 2-(2-nitrophenoxy)acetohydrazide Chemical compound NNC(=O)COC1=CC=CC=C1[N+]([O-])=O QUTJSDSZEWQPSX-UHFFFAOYSA-N 0.000 description 1
- CZXFCCXLFQCYBK-UHFFFAOYSA-N 2-(2-nitrophenyl)sulfanylacetohydrazide Chemical compound NNC(=O)CSC1=CC=CC=C1[N+]([O-])=O CZXFCCXLFQCYBK-UHFFFAOYSA-N 0.000 description 1
- QQUDGIWFYLRKBY-UHFFFAOYSA-N 2-(3-chloro-2-methylphenyl)sulfanylacetohydrazide Chemical compound CC1=C(Cl)C=CC=C1SCC(=O)NN QQUDGIWFYLRKBY-UHFFFAOYSA-N 0.000 description 1
- QGULAZOKPKAIRW-UHFFFAOYSA-N 2-(3-methoxyphenoxy)acetohydrazide Chemical compound COC1=CC=CC(OCC(=O)NN)=C1 QGULAZOKPKAIRW-UHFFFAOYSA-N 0.000 description 1
- LMSQEBMMWJHLQK-UHFFFAOYSA-N 2-(3-methoxyphenyl)sulfanylacetic acid Chemical compound COC1=CC=CC(SCC(O)=O)=C1 LMSQEBMMWJHLQK-UHFFFAOYSA-N 0.000 description 1
- XTTHKVPUJUYDDK-UHFFFAOYSA-N 2-(3-methylphenoxy)acetohydrazide Chemical compound CC1=CC=CC(OCC(=O)NN)=C1 XTTHKVPUJUYDDK-UHFFFAOYSA-N 0.000 description 1
- RKZQWMLTVDXDGV-UHFFFAOYSA-N 2-(4-bromophenoxy)acetohydrazide Chemical compound NNC(=O)COC1=CC=C(Br)C=C1 RKZQWMLTVDXDGV-UHFFFAOYSA-N 0.000 description 1
- JXQVZCTYFYWQGN-UHFFFAOYSA-N 2-(4-chloro-2-methylphenoxy)acetohydrazide Chemical compound CC1=CC(Cl)=CC=C1OCC(=O)NN JXQVZCTYFYWQGN-UHFFFAOYSA-N 0.000 description 1
- IESQBZMQMDXTCE-UHFFFAOYSA-N 2-(4-chloro-3,5-dimethylphenoxy)acetohydrazide Chemical compound CC1=CC(OCC(=O)NN)=CC(C)=C1Cl IESQBZMQMDXTCE-UHFFFAOYSA-N 0.000 description 1
- KFEHAYRYAXSMBJ-UHFFFAOYSA-N 2-(4-chlorophenoxy)acetohydrazide Chemical compound NNC(=O)COC1=CC=C(Cl)C=C1 KFEHAYRYAXSMBJ-UHFFFAOYSA-N 0.000 description 1
- DEMQFOZUWVKLMD-UHFFFAOYSA-N 2-(4-ethylphenyl)sulfanylacetohydrazide Chemical compound CCC1=CC=C(SCC(=O)NN)C=C1 DEMQFOZUWVKLMD-UHFFFAOYSA-N 0.000 description 1
- FHYDKLWLDUMAIU-UHFFFAOYSA-N 2-(4-methoxyphenoxy)acetohydrazide Chemical compound COC1=CC=C(OCC(=O)NN)C=C1 FHYDKLWLDUMAIU-UHFFFAOYSA-N 0.000 description 1
- XSDBWFOMCHASMG-UHFFFAOYSA-N 2-(4-methyl-2-nitrophenyl)sulfanylacetohydrazide Chemical compound CC1=CC=C(SCC(=O)NN)C([N+]([O-])=O)=C1 XSDBWFOMCHASMG-UHFFFAOYSA-N 0.000 description 1
- BJAPYOSQJTZYQH-UHFFFAOYSA-N 2-(4-methylphenoxy)acetohydrazide Chemical compound CC1=CC=C(OCC(=O)NN)C=C1 BJAPYOSQJTZYQH-UHFFFAOYSA-N 0.000 description 1
- BDPKZWIKLVUGKS-UHFFFAOYSA-N 2-(4-nitrophenoxy)acetohydrazide Chemical compound NNC(=O)COC1=CC=C([N+]([O-])=O)C=C1 BDPKZWIKLVUGKS-UHFFFAOYSA-N 0.000 description 1
- OTHJZGVDIXJZRR-UHFFFAOYSA-N 2-(4-nitrophenyl)sulfanylacetohydrazide Chemical compound NNC(=O)CSC1=CC=C([N+]([O-])=O)C=C1 OTHJZGVDIXJZRR-UHFFFAOYSA-N 0.000 description 1
- PMTVEXBJLIRTEJ-UHFFFAOYSA-N 2-methyl-4-nitrosophenol Chemical compound CC1=CC(N=O)=CC=C1O PMTVEXBJLIRTEJ-UHFFFAOYSA-N 0.000 description 1
- VTWDKFNVVLAELH-UHFFFAOYSA-N 2-methylcyclohexa-2,5-diene-1,4-dione Chemical compound CC1=CC(=O)C=CC1=O VTWDKFNVVLAELH-UHFFFAOYSA-N 0.000 description 1
- XSONSBDQIFBIOY-UHFFFAOYSA-N 2-phenoxyacetohydrazide Chemical compound NNC(=O)COC1=CC=CC=C1 XSONSBDQIFBIOY-UHFFFAOYSA-N 0.000 description 1
- CHPUPDAFQCQXCS-UHFFFAOYSA-N 2-phenyl-2-sulfanylacetohydrazide Chemical compound NNC(=O)C(S)C1=CC=CC=C1 CHPUPDAFQCQXCS-UHFFFAOYSA-N 0.000 description 1
- FPTCVTJCJMVIDV-UHFFFAOYSA-N 2-phenylacetohydrazide Chemical compound NNC(=O)CC1=CC=CC=C1 FPTCVTJCJMVIDV-UHFFFAOYSA-N 0.000 description 1
- XGCZABZDVJOWTL-UHFFFAOYSA-N 3-methyl-4-nitrosophenol Chemical compound CC1=CC(O)=CC=C1N=O XGCZABZDVJOWTL-UHFFFAOYSA-N 0.000 description 1
- 241000235349 Ascomycota Species 0.000 description 1
- 241000221198 Basidiomycota Species 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 235000001258 Cinchona calisaya Nutrition 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- 241001465754 Metazoa 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
- 208000031888 Mycoses Diseases 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 108010009736 Protein Hydrolysates Proteins 0.000 description 1
- 240000003768 Solanum lycopersicum Species 0.000 description 1
- 241000082085 Verticillium <Phyllachorales> Species 0.000 description 1
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical class ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
- 230000000895 acaricidal effect Effects 0.000 description 1
- 239000000642 acaricide Substances 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000003570 air Substances 0.000 description 1
- 125000002877 alkyl aryl group Chemical group 0.000 description 1
- 150000008055 alkyl aryl sulfonates Chemical class 0.000 description 1
- 150000008051 alkyl sulfates Chemical class 0.000 description 1
- 229940045714 alkyl sulfonate alkylating agent Drugs 0.000 description 1
- 150000008052 alkyl sulfonates Chemical class 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000001582 butter acid Substances 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 150000008422 chlorobenzenes Chemical class 0.000 description 1
- LOUPRKONTZGTKE-UHFFFAOYSA-N cinchonine Natural products C1C(C(C2)C=C)CCN2C1C(O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-UHFFFAOYSA-N 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 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
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 238000010410 dusting Methods 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000002191 fatty alcohols Chemical class 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- 231100000162 fungitoxic Toxicity 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 238000006698 hydrazinolysis reaction Methods 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 238000011081 inoculation Methods 0.000 description 1
- 239000002917 insecticide Substances 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
- 229920005610 lignin Polymers 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229910052901 montmorillonite Inorganic materials 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 230000003071 parasitic effect Effects 0.000 description 1
- 244000052769 pathogen Species 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- 239000003531 protein hydrolysate Substances 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 229960000948 quinine Drugs 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 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
- 239000003440 toxic substance Substances 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C251/72—Hydrazones
- C07C251/84—Hydrazones having doubly-bound carbon atoms of hydrazone groups being part of rings other than six-membered aromatic rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (13)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2410184A DE2410184A1 (de) | 1974-03-04 | 1974-03-04 | Chinonoxim-acylhydrazon-derivate, verfahren zu ihrer herstellung, sowie ihre verwendung als fungizide |
| US05/553,874 US3972905A (en) | 1974-03-04 | 1975-02-27 | Quinonemonoxime-arylacylhydrazones |
| BE153865A BE826128A (fr) | 1974-03-04 | 1975-02-28 | Nouvelles quinonoxime-acylhydrazones leur procede de preparation et leur application comme fongicides |
| IL46727A IL46727A (en) | 1974-03-04 | 1975-02-28 | Quinonoxime-acylhydrazone derivatives their preparation and fungicidal compositions containing them |
| DK84175*#A DK133280C (da) | 1974-03-04 | 1975-03-03 | Fungicidt virksomme quinonoxim-acylhydrazon-derivater |
| GB868175A GB1454725A (en) | 1974-03-04 | 1975-03-03 | Quinonoxime-acylhydrazone derivatives their preparation and their use as fungicides |
| LU71945A LU71945A1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1974-03-04 | 1975-03-03 | |
| BR1253/75A BR7501253A (pt) | 1974-03-04 | 1975-03-03 | Processo para a preparacao de derivados da quinona-oxima-acil-hidrazona e composicoes fungicidas a base destes |
| IE441/75A IE41217B1 (en) | 1974-03-04 | 1975-03-03 | Quinonoxime - aclhydrazone derivatives their preperation and their use as fungicides |
| NL7502543A NL7502543A (nl) | 1974-03-04 | 1975-03-04 | Werkwijze voor het bereiden van chinonoxime- acylhydrazonderivaten alsmede de toepassing daarvan als fungiciden. |
| JP50025699A JPS50123643A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1974-03-04 | 1975-03-04 | |
| FR7506667A FR2263234B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1974-03-04 | 1975-03-04 | |
| JP50025700A JPS50121429A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1974-03-04 | 1975-03-04 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2410184A DE2410184A1 (de) | 1974-03-04 | 1974-03-04 | Chinonoxim-acylhydrazon-derivate, verfahren zu ihrer herstellung, sowie ihre verwendung als fungizide |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2410184A1 true DE2410184A1 (de) | 1975-10-02 |
Family
ID=5908998
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2410184A Pending DE2410184A1 (de) | 1974-03-04 | 1974-03-04 | Chinonoxim-acylhydrazon-derivate, verfahren zu ihrer herstellung, sowie ihre verwendung als fungizide |
Country Status (12)
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2947772A1 (de) * | 1978-11-29 | 1980-06-12 | Montedison Spa | Praeparate zur behandlung und/oder immunisierung von nutzpflanzen gegen fungusinfektionen |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7799567B1 (en) * | 1999-03-10 | 2010-09-21 | Mesosystems Technology, Inc. | Air sampler based on virtual impaction and actual impaction |
| PL2490952T3 (pl) | 2009-10-22 | 2016-04-29 | Essity Hygiene & Health Ab | Składane pudło kartonowe |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE526520A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1953-02-25 |
-
1974
- 1974-03-04 DE DE2410184A patent/DE2410184A1/de active Pending
-
1975
- 1975-02-27 US US05/553,874 patent/US3972905A/en not_active Expired - Lifetime
- 1975-02-28 BE BE153865A patent/BE826128A/xx unknown
- 1975-02-28 IL IL46727A patent/IL46727A/en unknown
- 1975-03-03 LU LU71945A patent/LU71945A1/xx unknown
- 1975-03-03 IE IE441/75A patent/IE41217B1/xx unknown
- 1975-03-03 GB GB868175A patent/GB1454725A/en not_active Expired
- 1975-03-03 BR BR1253/75A patent/BR7501253A/pt unknown
- 1975-03-03 DK DK84175*#A patent/DK133280C/da active
- 1975-03-04 NL NL7502543A patent/NL7502543A/xx unknown
- 1975-03-04 FR FR7506667A patent/FR2263234B1/fr not_active Expired
- 1975-03-04 JP JP50025700A patent/JPS50121429A/ja active Pending
- 1975-03-04 JP JP50025699A patent/JPS50123643A/ja active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2947772A1 (de) * | 1978-11-29 | 1980-06-12 | Montedison Spa | Praeparate zur behandlung und/oder immunisierung von nutzpflanzen gegen fungusinfektionen |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2263234B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1978-09-29 |
| JPS50123643A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1975-09-29 |
| BR7501253A (pt) | 1975-12-02 |
| JPS50121429A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1975-09-23 |
| NL7502543A (nl) | 1975-09-08 |
| GB1454725A (en) | 1976-11-03 |
| DK133280B (da) | 1976-04-20 |
| IE41217L (en) | 1975-09-04 |
| IL46727A (en) | 1977-11-30 |
| IL46727A0 (en) | 1975-04-25 |
| BE826128A (fr) | 1975-08-28 |
| DK133280C (da) | 1976-09-20 |
| IE41217B1 (en) | 1979-11-07 |
| US3972905A (en) | 1976-08-03 |
| DK84175A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1975-09-05 |
| FR2263234A1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1975-10-03 |
| LU71945A1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1976-02-04 |
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