SU1111675A3 - Фунгицидна композици - Google Patents
Фунгицидна композици Download PDFInfo
- Publication number
- SU1111675A3 SU1111675A3 SU782625595A SU2625595A SU1111675A3 SU 1111675 A3 SU1111675 A3 SU 1111675A3 SU 782625595 A SU782625595 A SU 782625595A SU 2625595 A SU2625595 A SU 2625595A SU 1111675 A3 SU1111675 A3 SU 1111675A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- aminoquinazoline
- ethyl
- methyl
- chloro
- chlorine
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 20
- 230000000855 fungicidal effect Effects 0.000 title claims abstract description 9
- DRYRBWIFRVMRPV-UHFFFAOYSA-N quinazolin-4-amine Chemical class C1=CC=C2C(N)=NC=NC2=C1 DRYRBWIFRVMRPV-UHFFFAOYSA-N 0.000 claims abstract description 9
- -1 methoxy, methylthio Chemical group 0.000 claims description 51
- 150000001875 compounds Chemical class 0.000 claims description 23
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 9
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 9
- 239000000460 chlorine Substances 0.000 claims description 9
- 229910052801 chlorine Inorganic materials 0.000 claims description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 claims description 5
- 229920005552 sodium lignosulfonate Polymers 0.000 claims description 5
- 239000005909 Kieselgur Substances 0.000 claims description 4
- 239000004372 Polyvinyl alcohol Substances 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 229920002451 polyvinyl alcohol Polymers 0.000 claims description 4
- 239000000741 silica gel Substances 0.000 claims description 4
- 229910002027 silica gel Inorganic materials 0.000 claims description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
- 229910052794 bromium Inorganic materials 0.000 claims description 3
- 229940051841 polyoxyethylene ether Drugs 0.000 claims description 3
- 229920000056 polyoxyethylene ether Polymers 0.000 claims description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 239000004927 clay Substances 0.000 claims description 2
- 150000002431 hydrogen Chemical class 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
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 239000011593 sulfur Chemical group 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
- 239000000377 silicon dioxide Substances 0.000 claims 1
- 229920002554 vinyl polymer Polymers 0.000 claims 1
- 239000004563 wettable powder Substances 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 abstract 1
- 125000003277 amino group Chemical group 0.000 abstract 1
- 150000003246 quinazolines Chemical class 0.000 abstract 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 24
- CZAAKPFIWJXPQT-UHFFFAOYSA-N quinazolin-2-amine Chemical compound C1=CC=CC2=NC(N)=NC=C21 CZAAKPFIWJXPQT-UHFFFAOYSA-N 0.000 description 23
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 21
- 238000012360 testing method Methods 0.000 description 16
- QRZGSJAFIKQJBR-UHFFFAOYSA-N 4-ethylquinazolin-2-amine Chemical compound C1=CC=C2C(CC)=NC(N)=NC2=C1 QRZGSJAFIKQJBR-UHFFFAOYSA-N 0.000 description 15
- 241000196324 Embryophyta Species 0.000 description 15
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 208000015181 infectious disease Diseases 0.000 description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 7
- 238000005507 spraying Methods 0.000 description 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- 241000209094 Oryza Species 0.000 description 6
- 231100000208 phytotoxic Toxicity 0.000 description 6
- 230000000885 phytotoxic effect Effects 0.000 description 6
- 239000000725 suspension Substances 0.000 description 6
- 240000008067 Cucumis sativus Species 0.000 description 5
- 239000007900 aqueous suspension Substances 0.000 description 5
- 239000013078 crystal Substances 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- UGRMITBWUVWUEB-UHFFFAOYSA-N 1-$l^{1}-oxidanyl-3-methylbenzene Chemical group CC1=CC=CC([O])=C1 UGRMITBWUVWUEB-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- GVRRXASZZAKBMN-UHFFFAOYSA-N 4-chloroquinazoline Chemical compound C1=CC=C2C(Cl)=NC=NC2=C1 GVRRXASZZAKBMN-UHFFFAOYSA-N 0.000 description 3
- 235000010799 Cucumis sativus var sativus Nutrition 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 241000607479 Yersinia pestis Species 0.000 description 3
- 238000007605 air drying Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 244000000010 microbial pathogen Species 0.000 description 3
- OFTCIAFFGMUPJQ-UHFFFAOYSA-N n-(5-phenoxypentyl)quinazolin-4-amine Chemical compound N=1C=NC2=CC=CC=C2C=1NCCCCCOC1=CC=CC=C1 OFTCIAFFGMUPJQ-UHFFFAOYSA-N 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- QPUYECUOLPXSFR-UHFFFAOYSA-N 1-methylnaphthalene Chemical compound C1=CC=C2C(C)=CC=CC2=C1 QPUYECUOLPXSFR-UHFFFAOYSA-N 0.000 description 2
- PFYIBMHKWYYYPD-UHFFFAOYSA-N 4-(3-phenoxypropyl)quinazolin-2-amine Chemical compound O(C1=CC=CC=C1)CCCC1=NC(=NC2=CC=CC=C12)N PFYIBMHKWYYYPD-UHFFFAOYSA-N 0.000 description 2
- VQLBYGXUGMXDKX-UHFFFAOYSA-N 4-[2-(2-methylphenoxy)ethyl]quinazolin-2-amine Chemical compound CC1=C(OCCC2=NC(=NC3=CC=CC=C23)N)C=CC=C1 VQLBYGXUGMXDKX-UHFFFAOYSA-N 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- 241000227653 Lycopersicon Species 0.000 description 2
- 235000007688 Lycopersicon esculentum Nutrition 0.000 description 2
- 235000007164 Oryza sativa Nutrition 0.000 description 2
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 206010064127 Solar lentigo Diseases 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 235000009566 rice Nutrition 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- WWTBZEKOSBFBEM-SPWPXUSOSA-N (2s)-2-[[2-benzyl-3-[hydroxy-[(1r)-2-phenyl-1-(phenylmethoxycarbonylamino)ethyl]phosphoryl]propanoyl]amino]-3-(1h-indol-3-yl)propanoic acid Chemical compound N([C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)O)C(=O)C(CP(O)(=O)[C@H](CC=1C=CC=CC=1)NC(=O)OCC=1C=CC=CC=1)CC1=CC=CC=C1 WWTBZEKOSBFBEM-SPWPXUSOSA-N 0.000 description 1
- STBLNCCBQMHSRC-BATDWUPUSA-N (2s)-n-[(3s,4s)-5-acetyl-7-cyano-4-methyl-1-[(2-methylnaphthalen-1-yl)methyl]-2-oxo-3,4-dihydro-1,5-benzodiazepin-3-yl]-2-(methylamino)propanamide Chemical compound O=C1[C@@H](NC(=O)[C@H](C)NC)[C@H](C)N(C(C)=O)C2=CC(C#N)=CC=C2N1CC1=C(C)C=CC2=CC=CC=C12 STBLNCCBQMHSRC-BATDWUPUSA-N 0.000 description 1
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
- VVCMGAUPZIKYTH-VGHSCWAPSA-N 2-acetyloxybenzoic acid;[(2s,3r)-4-(dimethylamino)-3-methyl-1,2-diphenylbutan-2-yl] propanoate;1,3,7-trimethylpurine-2,6-dione Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O.CN1C(=O)N(C)C(=O)C2=C1N=CN2C.C([C@](OC(=O)CC)([C@H](C)CN(C)C)C=1C=CC=CC=1)C1=CC=CC=C1 VVCMGAUPZIKYTH-VGHSCWAPSA-N 0.000 description 1
- DXVQSHRBALIFBC-UHFFFAOYSA-N 3-phenoxypropan-1-amine Chemical compound NCCCOC1=CC=CC=C1 DXVQSHRBALIFBC-UHFFFAOYSA-N 0.000 description 1
- UDCBBTROXIMTQZ-UHFFFAOYSA-N 4-(2-phenylsulfanylethyl)quinazolin-2-amine Chemical compound C1(=CC=CC=C1)SCCC1=NC(=NC2=CC=CC=C12)N UDCBBTROXIMTQZ-UHFFFAOYSA-N 0.000 description 1
- ILIBKLJLEYSSME-UHFFFAOYSA-N 4-(6-phenoxyhexyl)quinazolin-2-amine Chemical compound O(C1=CC=CC=C1)CCCCCCC1=NC(=NC2=CC=CC=C12)N ILIBKLJLEYSSME-UHFFFAOYSA-N 0.000 description 1
- JHYLVVGEIKPSOX-UHFFFAOYSA-N 4-[2-(3,4-dimethylthiophen-2-yl)oxyethyl]quinazolin-2-amine Chemical compound CC1=C(SC=C1C)OCCC1=NC(=NC2=CC=CC=C12)N JHYLVVGEIKPSOX-UHFFFAOYSA-N 0.000 description 1
- JOHCKQPXWBBCBX-UHFFFAOYSA-N 4-[5-(2-chlorophenoxy)pentyl]quinazolin-2-amine Chemical compound ClC1=C(OCCCCCC2=NC(=NC3=CC=CC=C23)N)C=CC=C1 JOHCKQPXWBBCBX-UHFFFAOYSA-N 0.000 description 1
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 1
- WUBBRNOQWQTFEX-UHFFFAOYSA-N 4-aminosalicylic acid Chemical compound NC1=CC=C(C(O)=O)C(O)=C1 WUBBRNOQWQTFEX-UHFFFAOYSA-N 0.000 description 1
- KVEHRMVZMIBYCO-UHFFFAOYSA-N 4-chloro-2-(4-methylphenyl)quinazoline Chemical compound C1=CC(C)=CC=C1C1=NC(Cl)=C(C=CC=C2)C2=N1 KVEHRMVZMIBYCO-UHFFFAOYSA-N 0.000 description 1
- XNILKVADCMYCQT-UHFFFAOYSA-N 4-chloro-6-methylquinazoline Chemical compound N1=CN=C(Cl)C2=CC(C)=CC=C21 XNILKVADCMYCQT-UHFFFAOYSA-N 0.000 description 1
- CMLVHSVFSYNMGM-WYMLVPIESA-N 4-n-[7-chloro-2-[(e)-2-(2-chlorophenyl)ethenyl]quinolin-4-yl]-1-n,1-n-diethylpentane-1,4-diamine Chemical group N=1C2=CC(Cl)=CC=C2C(NC(C)CCCN(CC)CC)=CC=1\C=C\C1=CC=CC=C1Cl CMLVHSVFSYNMGM-WYMLVPIESA-N 0.000 description 1
- WXFMHWZCFFQMAP-UHFFFAOYSA-N 5-phenoxypentan-1-amine Chemical compound NCCCCCOC1=CC=CC=C1 WXFMHWZCFFQMAP-UHFFFAOYSA-N 0.000 description 1
- 241000222235 Colletotrichum orbiculare Species 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
- 241000221785 Erysiphales Species 0.000 description 1
- 241000233866 Fungi Species 0.000 description 1
- 206010061217 Infestation Diseases 0.000 description 1
- 208000031888 Mycoses Diseases 0.000 description 1
- 101100513046 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) eth-1 gene Proteins 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 231100000674 Phytotoxicity Toxicity 0.000 description 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical class [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
- 240000003768 Solanum lycopersicum Species 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
- 241000589634 Xanthomonas Species 0.000 description 1
- SYKNUAWMBRIEKB-UHFFFAOYSA-N [Cl].[Br] Chemical compound [Cl].[Br] SYKNUAWMBRIEKB-UHFFFAOYSA-N 0.000 description 1
- CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Substances CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000005219 brazing Methods 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 235000021329 brown rice Nutrition 0.000 description 1
- 230000001680 brushing effect Effects 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 229910052570 clay Inorganic materials 0.000 description 1
- 229940126208 compound 22 Drugs 0.000 description 1
- 229940125878 compound 36 Drugs 0.000 description 1
- 229940117389 dichlorobenzene Drugs 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 230000005087 leaf formation Effects 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- 235000011118 potassium hydroxide Nutrition 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 235000011182 sodium carbonates Nutrition 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene 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
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
- C07D239/72—Quinazolines; Hydrogenated quinazolines
- C07D239/86—Quinazolines; Hydrogenated quinazolines with hetero atoms directly attached in position 4
- C07D239/94—Nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
- C07D239/72—Quinazolines; Hydrogenated quinazolines
- C07D239/95—Quinazolines; Hydrogenated quinazolines with hetero atoms directly attached in positions 2 and 4
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Dentistry (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Agronomy & Crop Science (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)
- Taps Or Cocks (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP6703477A JPS5417123A (en) | 1977-06-07 | 1977-06-07 | Agricultural and horticultural microbicide |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU1111675A3 true SU1111675A3 (ru) | 1984-08-30 |
Family
ID=13333175
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU782625595A SU1111675A3 (ru) | 1977-06-07 | 1978-06-06 | Фунгицидна композици |
Country Status (12)
| Country | Link |
|---|---|
| US (2) | US4213987A (enExample) |
| JP (1) | JPS5417123A (enExample) |
| BR (1) | BR7803642A (enExample) |
| CA (2) | CA1086642A (enExample) |
| CH (1) | CH636751A5 (enExample) |
| DE (1) | DE2824768A1 (enExample) |
| FR (1) | FR2393531A1 (enExample) |
| GB (2) | GB1582407A (enExample) |
| NL (1) | NL189257C (enExample) |
| PH (1) | PH13938A (enExample) |
| SU (1) | SU1111675A3 (enExample) |
| ZA (1) | ZA783229B (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2721418C2 (ru) * | 2013-02-01 | 2020-05-19 | Веллстат Терапьютикс Корпорейшн | Соединения амина, имеющие противовоспалительную, противогрибковую, противопаразитарную и противораковую активность |
Families Citing this family (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1582407A (en) * | 1977-06-07 | 1981-01-07 | Worcester Controls Uk Ltd | Annular seals |
| JPS5576804A (en) * | 1978-12-06 | 1980-06-10 | Sankyo Co Ltd | Agricultural and horticultural microbicide |
| PH20344A (en) * | 1981-01-29 | 1986-12-04 | Sankyo Co | Aminopyrimidine derivatives, processes for their preparation, and fungicidal, insecticidal and acaricidal compositions containing them |
| US4431440A (en) * | 1981-02-20 | 1984-02-14 | American Cyanamid Company | Method to alter or control the development and/or the life cycle of various plant species |
| GB2116678B (en) * | 1982-02-08 | 1986-04-30 | Hitachi Metals Ltd | Ball valves |
| KR930009443B1 (ko) * | 1985-03-14 | 1993-10-04 | 상꾜 가부시끼가이샤 | 페녹시알킬아미노 피리미딘 유도체의 제조방법 |
| JPS6267A (ja) * | 1985-03-14 | 1987-01-06 | Sankyo Co Ltd | フエノキシアルキルアミン誘導体、その製法および殺虫殺ダニ剤 |
| DE3642452A1 (de) * | 1986-12-12 | 1988-06-23 | Bayer Ag | Substituierte 4-amino-pyrimidine |
| IL89027A (en) * | 1988-01-29 | 1993-01-31 | Lilly Co Eli | Quinazoline derivatives, process for their preparation and fungicidal, insecticidal and miticidal compositions containing them |
| IL89029A (en) * | 1988-01-29 | 1993-01-31 | Lilly Co Eli | Fungicidal quinoline and cinnoline derivatives, compositions containing them, and fungicidal methods of using them |
| GT198900008A (es) * | 1988-01-29 | 1990-07-17 | Derivados de quinolina, quinazolina y cinolina. | |
| US5114939A (en) * | 1988-01-29 | 1992-05-19 | Dowelanco | Substituted quinolines and cinnolines as fungicides |
| US5411963A (en) * | 1988-01-29 | 1995-05-02 | Dowelanco | Quinazoline derivatives |
| US5124333A (en) * | 1989-08-02 | 1992-06-23 | Ube Industries, Ltd. | Aminopyrimidine derivatives and harmful organisms preventive agent |
| NZ238817A (en) * | 1990-07-18 | 1992-09-25 | Sumitomo Chemical Co | Pyrimidine derivatives, preparation and use as insecticides, acaricides and fungicides |
| US5236924A (en) * | 1990-07-18 | 1993-08-17 | Sumitomo Chemical Co., Ltd. | Pyrimidine derivatives and fungicides and/or acaricides containing them as active ingredient |
| PT100905A (pt) * | 1991-09-30 | 1994-02-28 | Eisai Co Ltd | Compostos heterociclicos azotados biciclicos contendo aneis de benzeno, ciclo-hexano ou piridina e de pirimidina, piridina ou imidazol substituidos e composicoes farmaceuticas que os contem |
| DE69403535T2 (de) * | 1993-04-02 | 1997-11-13 | Ube Industries | Phenoxyalkylamin Derivate mit insecticider, akarizider und fungizider Wirkung und Verfahren zu ihrer Herstellung |
| US5415877A (en) * | 1993-04-23 | 1995-05-16 | Church & Dwight Co., Inc. | Bicarbonate fungicide product with a combination of surfactant ingredients |
| US5614627A (en) * | 1993-09-10 | 1997-03-25 | Eisai Co., Ltd. | Quinazoline compounds |
| WO2001032632A2 (en) * | 1999-11-01 | 2001-05-10 | Eli Lilly And Company | Pharmaceutically active 4-substituted pyrimidine derivatives |
| AU2001280836A1 (en) * | 2000-07-31 | 2002-02-13 | Meditech Pharmaceuticals, Inc. | Compounds, compositions, and methods for the treatment of plant bacterial and fungal infections |
| WO2017004405A1 (en) * | 2015-07-01 | 2017-01-05 | Northwestern University | Substituted quinazoline compounds and uses thereof for modulating glucocerebrosidase activity |
| CN110194761B (zh) * | 2019-07-05 | 2021-08-20 | 华东理工大学 | 喹唑啉基羧酸酯类衍生物及其抗菌用途 |
| CN110627731A (zh) * | 2019-10-09 | 2019-12-31 | 贵州大学 | 一类4-氨基喹唑啉接丙烯酰胺类化合物及其制备方法和应用 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH492395A (de) * | 1966-04-26 | 1970-06-30 | Sandoz Ag | Mittel zur Bekämpfung von Pflanzenschädlingen und Verwendung des Mittels |
| FR1528020A (fr) * | 1966-04-26 | 1968-06-07 | Sandoz Sa | Procédé et produit utilisables en phytopharmacie |
| GB1199768A (en) * | 1966-10-31 | 1970-07-22 | Pfizer & Co C | Nitrogen Heterocycles and process for their preparation |
| US3560619A (en) * | 1967-01-03 | 1971-02-02 | Mead Johnson & Co | Aminoquinazolines and quinazolones in treatment of coccidiosis |
| US3574210A (en) * | 1967-07-13 | 1971-04-06 | Squibb & Sons Inc | 2,4-disubstituted-6-nitro-and 6-a minoquinazolines |
| FR2077803B1 (enExample) * | 1970-02-16 | 1973-03-16 | Innothera Lab Sa | |
| SU446506A1 (ru) * | 1972-06-30 | 1974-10-15 | Всесоюзный Научно-Исследовательский Химико-Фармацевтический Институт Имени Серго Орджоникидзе | Способ получени производных 4-аминохиназолинов |
| GB1582407A (en) * | 1977-06-07 | 1981-01-07 | Worcester Controls Uk Ltd | Annular seals |
-
1976
- 1976-08-04 GB GB32541/76A patent/GB1582407A/en not_active Expired
-
1977
- 1977-06-07 JP JP6703477A patent/JPS5417123A/ja active Granted
-
1978
- 1978-05-30 US US05/910,117 patent/US4213987A/en not_active Expired - Lifetime
- 1978-05-31 GB GB24715/78A patent/GB1598880A/en not_active Expired
- 1978-06-02 PH PH21227A patent/PH13938A/en unknown
- 1978-06-06 DE DE19782824768 patent/DE2824768A1/de active Granted
- 1978-06-06 SU SU782625595A patent/SU1111675A3/ru active
- 1978-06-06 NL NLAANVRAGE7806153,A patent/NL189257C/xx not_active IP Right Cessation
- 1978-06-06 CA CA304,843A patent/CA1086642A/en not_active Expired
- 1978-06-06 ZA ZA00783229A patent/ZA783229B/xx unknown
- 1978-06-06 BR BR7803642A patent/BR7803642A/pt unknown
- 1978-06-06 CH CH618578A patent/CH636751A5/de not_active IP Right Cessation
- 1978-06-07 FR FR787817007A patent/FR2393531A1/fr active Granted
-
1980
- 1980-03-28 US US06/134,794 patent/US4323680A/en not_active Expired - Lifetime
-
1981
- 1981-02-18 CA CA000371218A patent/CA1230339B/en not_active Expired
Non-Patent Citations (1)
| Title |
|---|
| 1. Патент US № 3998951, кл. А 01 N 9/22, опублик. 1976. 2. Патент JP № 43-29033, кл. 30 F, опублик. 1968 (прототип). * |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2721418C2 (ru) * | 2013-02-01 | 2020-05-19 | Веллстат Терапьютикс Корпорейшн | Соединения амина, имеющие противовоспалительную, противогрибковую, противопаразитарную и противораковую активность |
| US10934284B2 (en) | 2013-02-01 | 2021-03-02 | Wellstat Therapeutics Corporation | Aminoquinazoline compounds having anti-inflammatory, antifungal, antiparasitic, and anticancer activity |
| US12139483B2 (en) | 2013-02-01 | 2024-11-12 | Pharma Cinq, Llc | Imidazoquinolyl compounds having anti-inflammatory, antifungal, antiparasitic, and anticancer activity |
Also Published As
| Publication number | Publication date |
|---|---|
| NL189257C (nl) | 1993-02-16 |
| BR7803642A (pt) | 1979-01-09 |
| US4213987A (en) | 1980-07-22 |
| JPS6120522B2 (enExample) | 1986-05-22 |
| PH13938A (en) | 1980-11-04 |
| GB1582407A (en) | 1981-01-07 |
| CA1086642A (en) | 1980-09-30 |
| US4323680A (en) | 1982-04-06 |
| JPS5417123A (en) | 1979-02-08 |
| CA1230339B (en) | 1987-12-15 |
| FR2393531A1 (fr) | 1979-01-05 |
| GB1598880A (en) | 1981-09-23 |
| ZA783229B (en) | 1979-06-27 |
| NL189257B (nl) | 1992-09-16 |
| DE2824768A1 (de) | 1978-12-14 |
| NL7806153A (nl) | 1978-12-11 |
| FR2393531B1 (enExample) | 1984-11-30 |
| DE2824768C2 (enExample) | 1989-10-12 |
| CH636751A5 (de) | 1983-06-30 |
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