DE2239892A1 - Mittel zur bekaempfung von pflanzenpathogenen organismen - Google Patents
Mittel zur bekaempfung von pflanzenpathogenen organismenInfo
- Publication number
- DE2239892A1 DE2239892A1 DE2239892A DE2239892A DE2239892A1 DE 2239892 A1 DE2239892 A1 DE 2239892A1 DE 2239892 A DE2239892 A DE 2239892A DE 2239892 A DE2239892 A DE 2239892A DE 2239892 A1 DE2239892 A1 DE 2239892A1
- Authority
- DE
- Germany
- Prior art keywords
- quinoline
- triazolo
- group
- dihydro
- radical
- 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.)
- Withdrawn
Links
- 244000052769 pathogen Species 0.000 title claims description 5
- 150000001875 compounds Chemical class 0.000 claims description 77
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 53
- -1 s-triazolo (4,3-a) quinoline compound Chemical class 0.000 claims description 52
- 238000000034 method Methods 0.000 claims description 27
- 239000000203 mixture Substances 0.000 claims description 20
- 239000003795 chemical substances by application Substances 0.000 claims description 18
- 150000003254 radicals Chemical class 0.000 claims description 16
- 230000003032 phytopathogenic effect Effects 0.000 claims description 15
- 150000003839 salts Chemical class 0.000 claims description 15
- 239000002253 acid Substances 0.000 claims description 14
- 125000005843 halogen group Chemical group 0.000 claims description 12
- 239000004480 active ingredient Substances 0.000 claims description 11
- 239000002270 dispersing agent Substances 0.000 claims description 11
- 125000003277 amino group Chemical group 0.000 claims description 10
- 239000007787 solid Substances 0.000 claims description 10
- 125000001424 substituent group Chemical group 0.000 claims description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- PIRYKGLQLCKQPG-UHFFFAOYSA-N [1,2,4]triazolo[4,3-a]quinoline Chemical class C1=CC=C2N3C=NN=C3C=CC2=C1 PIRYKGLQLCKQPG-UHFFFAOYSA-N 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 125000003282 alkyl amino group Chemical group 0.000 claims description 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 6
- WZKSXHQDXQKIQJ-UHFFFAOYSA-N F[C](F)F Chemical compound F[C](F)F WZKSXHQDXQKIQJ-UHFFFAOYSA-N 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- WSVBLWJMUYGBTD-UHFFFAOYSA-N 9-chloro-4,5-dihydro-[1,2,4]triazolo[4,3-a]quinoline Chemical compound C1CC2=NN=CN2C2=C1C=CC=C2Cl WSVBLWJMUYGBTD-UHFFFAOYSA-N 0.000 claims description 4
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 4
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 4
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical class [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims description 4
- 239000011707 mineral Substances 0.000 claims description 4
- 229910052700 potassium Inorganic materials 0.000 claims description 4
- 239000011591 potassium Chemical group 0.000 claims description 4
- 229910052708 sodium Inorganic materials 0.000 claims description 4
- 239000011734 sodium Substances 0.000 claims description 4
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical group 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 claims description 3
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 3
- CFHIDWOYWUOIHU-UHFFFAOYSA-N oxomethyl Chemical compound O=[CH] CFHIDWOYWUOIHU-UHFFFAOYSA-N 0.000 claims description 3
- ZMZDMBWJUHKJPS-UHFFFAOYSA-M thiocyanate group Chemical group [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 claims description 3
- 229940055764 triaz Drugs 0.000 claims description 3
- ATPVHBJQSWKTAF-UHFFFAOYSA-N 1-methyl-4,5-dihydro-[1,2,4]triazolo[4,3-a]quinoline Chemical compound C1=CC=C2N3C(C)=NN=C3CCC2=C1 ATPVHBJQSWKTAF-UHFFFAOYSA-N 0.000 claims description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical group [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 2
- 125000004849 alkoxymethyl group Chemical group 0.000 claims description 2
- 239000004615 ingredient Substances 0.000 claims description 2
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 2
- ORGHESHFQPYLAO-UHFFFAOYSA-N vinyl radical Chemical compound C=[CH] ORGHESHFQPYLAO-UHFFFAOYSA-N 0.000 claims description 2
- 125000004970 halomethyl group Chemical group 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 55
- 241000196324 Embryophyta Species 0.000 description 34
- 241000209094 Oryza Species 0.000 description 31
- 235000007164 Oryza sativa Nutrition 0.000 description 31
- 235000009566 rice Nutrition 0.000 description 31
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 24
- 239000011541 reaction mixture Substances 0.000 description 23
- 239000000243 solution Substances 0.000 description 23
- 238000006243 chemical reaction Methods 0.000 description 22
- FGLRGMVWMQLOCO-UHFFFAOYSA-N 2h-triazolo[4,5-h]quinoline Chemical compound C1=CC2=CC=CN=C2C2=C1N=NN2 FGLRGMVWMQLOCO-UHFFFAOYSA-N 0.000 description 20
- 238000010992 reflux Methods 0.000 description 16
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- 239000000047 product Substances 0.000 description 15
- QMVCLSHKMIGEFN-UHFFFAOYSA-N quinolin-2-ylhydrazine Chemical compound C1=CC=CC2=NC(NN)=CC=C21 QMVCLSHKMIGEFN-UHFFFAOYSA-N 0.000 description 15
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 14
- 239000007788 liquid Substances 0.000 description 13
- 238000002844 melting Methods 0.000 description 13
- 230000008018 melting Effects 0.000 description 13
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 238000002360 preparation method Methods 0.000 description 9
- 239000002689 soil Substances 0.000 description 9
- 208000024891 symptom Diseases 0.000 description 9
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 8
- 239000004094 surface-active agent Substances 0.000 description 8
- 239000000725 suspension Substances 0.000 description 8
- 231100000674 Phytotoxicity Toxicity 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- 239000007921 spray Substances 0.000 description 7
- RQKYMHOXEANZSS-UHFFFAOYSA-N 3,4-dihydroquinolin-2-ylhydrazine Chemical compound C1=CC=C2CCC(NN)=NC2=C1 RQKYMHOXEANZSS-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 6
- 201000010099 disease Diseases 0.000 description 6
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 6
- 239000002244 precipitate Substances 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 239000012141 concentrate Substances 0.000 description 5
- 238000001704 evaporation Methods 0.000 description 5
- 239000003921 oil Substances 0.000 description 5
- 239000000376 reactant Substances 0.000 description 5
- 238000000926 separation method Methods 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- 238000001308 synthesis method Methods 0.000 description 5
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 4
- LABBQUDAKQLLRC-UHFFFAOYSA-N 9-chloro-[1,2,4]triazolo[4,3-a]quinoline Chemical compound C1=CC2=NN=CN2C2=C1C=CC=C2Cl LABBQUDAKQLLRC-UHFFFAOYSA-N 0.000 description 4
- 241000227653 Lycopersicon Species 0.000 description 4
- 238000005481 NMR spectroscopy Methods 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 238000004140 cleaning Methods 0.000 description 4
- 239000003995 emulsifying agent Substances 0.000 description 4
- 230000008020 evaporation Effects 0.000 description 4
- 235000019253 formic acid Nutrition 0.000 description 4
- 229910052736 halogen Inorganic materials 0.000 description 4
- 150000002367 halogens Chemical class 0.000 description 4
- 238000005984 hydrogenation reaction Methods 0.000 description 4
- QKFJKGMPGYROCL-UHFFFAOYSA-N phenyl isothiocyanate Chemical compound S=C=NC1=CC=CC=C1 QKFJKGMPGYROCL-UHFFFAOYSA-N 0.000 description 4
- 239000012429 reaction media Substances 0.000 description 4
- 238000001953 recrystallisation Methods 0.000 description 4
- BNKYRVKGPCWOCO-UHFFFAOYSA-N 1-chloro-[1,2,4]triazolo[4,3-a]quinoline Chemical group C1=CC=C2N3C(Cl)=NN=C3C=CC2=C1 BNKYRVKGPCWOCO-UHFFFAOYSA-N 0.000 description 3
- ABXBZWMYAZMVHH-UHFFFAOYSA-N 1-ethenyl-[1,2,4]triazolo[4,3-a]quinoline Chemical compound C1=CC=C2N3C(C=C)=NN=C3C=CC2=C1 ABXBZWMYAZMVHH-UHFFFAOYSA-N 0.000 description 3
- YBAGXSHWSZDEIP-UHFFFAOYSA-N 1-methylsulfanyl-[1,2,4]triazolo[4,3-a]quinoline Chemical compound C1=CC=C2N3C(SC)=NN=C3C=CC2=C1 YBAGXSHWSZDEIP-UHFFFAOYSA-N 0.000 description 3
- 240000008067 Cucumis sativus Species 0.000 description 3
- 241000233866 Fungi Species 0.000 description 3
- 206010061217 Infestation Diseases 0.000 description 3
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 3
- 244000046052 Phaseolus vulgaris Species 0.000 description 3
- 229920001213 Polysorbate 20 Polymers 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000000969 carrier Substances 0.000 description 3
- 235000021186 dishes Nutrition 0.000 description 3
- 239000000428 dust Substances 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- MNLJBCLBPMGVLY-UHFFFAOYSA-N ethyl [1,2,4]triazolo[4,3-a]quinoline-1-carboxylate Chemical compound C1=CC=C2N3C(C(=O)OCC)=NN=C3C=CC2=C1 MNLJBCLBPMGVLY-UHFFFAOYSA-N 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 239000012458 free base Substances 0.000 description 3
- 238000004452 microanalysis Methods 0.000 description 3
- 239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 description 3
- 235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 description 3
- 239000004576 sand Substances 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 238000010189 synthetic method Methods 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- MFESEHUNQZVWON-UHFFFAOYSA-N 1-(trifluoromethyl)-[1,2,4]triazolo[4,3-a]quinoline Chemical compound C1=CC=C2N3C(C(F)(F)F)=NN=C3C=CC2=C1 MFESEHUNQZVWON-UHFFFAOYSA-N 0.000 description 2
- NHHPFGOVGOVDGF-UHFFFAOYSA-N 1-ethylsulfanyl-[1,2,4]triazolo[4,3-a]quinoline Chemical compound C1=CC=C2N3C(SCC)=NN=C3C=CC2=C1 NHHPFGOVGOVDGF-UHFFFAOYSA-N 0.000 description 2
- VJXRNWAXFMJNEA-UHFFFAOYSA-N 1-propan-2-yl-[1,2,4]triazolo[4,3-a]quinoline Chemical compound C1=CC=C2N3C(C(C)C)=NN=C3C=CC2=C1 VJXRNWAXFMJNEA-UHFFFAOYSA-N 0.000 description 2
- GJIRTGKKCNFZTC-UHFFFAOYSA-N 1-propyl-[1,2,4]triazolo[4,3-a]quinoline Chemical compound C1=CC=C2N3C(CCC)=NN=C3C=CC2=C1 GJIRTGKKCNFZTC-UHFFFAOYSA-N 0.000 description 2
- GQJIGZUQXYCDJW-UHFFFAOYSA-N 2h-[1,2,4]triazolo[4,3-a]quinoline-1-thione Chemical compound C1=CC=C2N3C(=S)NN=C3C=CC2=C1 GQJIGZUQXYCDJW-UHFFFAOYSA-N 0.000 description 2
- YYFLDZZDOUDZQM-UHFFFAOYSA-N 3-[1-[[4-(3-phenylquinolin-2-yl)phenyl]methyl]piperidin-4-yl]-1h-benzimidazol-2-one Chemical compound O=C1NC2=CC=CC=C2N1C(CC1)CCN1CC(C=C1)=CC=C1C1=NC2=CC=CC=C2C=C1C1=CC=CC=C1 YYFLDZZDOUDZQM-UHFFFAOYSA-N 0.000 description 2
- FGBMEHAHHCGKTL-UHFFFAOYSA-N 4,5-dihydro-2h-[1,2,4]triazolo[4,3-a]quinolin-1-one Chemical compound C1=CC=C2N3C(O)=NN=C3CCC2=C1 FGBMEHAHHCGKTL-UHFFFAOYSA-N 0.000 description 2
- BVNHMBFSIICVAW-UHFFFAOYSA-N 4,5-dihydro-[1,2,4]triazolo[4,3-a]quinoline Chemical compound C1CC2=CC=CC=C2N2C1=NN=C2 BVNHMBFSIICVAW-UHFFFAOYSA-N 0.000 description 2
- CBAAZWAYQVAOGB-UHFFFAOYSA-N 5-chloro-1,4-dimethyl-[1,2,4]triazolo[4,3-a]quinoline Chemical compound C1=CC=C2N3C(C)=NN=C3C(C)=C(Cl)C2=C1 CBAAZWAYQVAOGB-UHFFFAOYSA-N 0.000 description 2
- KTKPZKFUPVZCGG-UHFFFAOYSA-N 7-methoxy-1-methyl-[1,2,4]triazolo[4,3-a]quinoline Chemical compound C1=CC2=NN=C(C)N2C2=CC=C(OC)C=C12 KTKPZKFUPVZCGG-UHFFFAOYSA-N 0.000 description 2
- YPWVAGZCIUPOBD-UHFFFAOYSA-N 7-methoxy-[1,2,4]triazolo[4,3-a]quinoline Chemical compound C1=CC2=NN=CN2C2=CC=C(OC)C=C12 YPWVAGZCIUPOBD-UHFFFAOYSA-N 0.000 description 2
- OSKQVMDFCDABCC-UHFFFAOYSA-N 9-ethyl-[1,2,4]triazolo[4,3-a]quinoline Chemical compound C1=CC2=NN=CN2C2=C1C=CC=C2CC OSKQVMDFCDABCC-UHFFFAOYSA-N 0.000 description 2
- HITDMAXFKLEEJP-UHFFFAOYSA-N 9-fluoro-[1,2,4]triazolo[4,3-a]quinoline Chemical compound C1=CC2=NN=CN2C2=C1C=CC=C2F HITDMAXFKLEEJP-UHFFFAOYSA-N 0.000 description 2
- XUIAQTNZZQDJDD-UHFFFAOYSA-N 9-methyl-[1,2,4]triazolo[4,3-a]quinoline Chemical compound C1=CC2=NN=CN2C2=C1C=CC=C2C XUIAQTNZZQDJDD-UHFFFAOYSA-N 0.000 description 2
- 229920001817 Agar Polymers 0.000 description 2
- 241000589155 Agrobacterium tumefaciens Species 0.000 description 2
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 241000222235 Colletotrichum orbiculare Species 0.000 description 2
- 235000010799 Cucumis sativus var sativus Nutrition 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 238000004566 IR spectroscopy Methods 0.000 description 2
- 235000007688 Lycopersicon esculentum Nutrition 0.000 description 2
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 2
- JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 235000010627 Phaseolus vulgaris Nutrition 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 239000008272 agar Substances 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 239000007900 aqueous suspension Substances 0.000 description 2
- 230000001580 bacterial effect Effects 0.000 description 2
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- 239000006227 byproduct Substances 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 239000007859 condensation product Substances 0.000 description 2
- ATDGTVJJHBUTRL-UHFFFAOYSA-N cyanogen bromide Chemical compound BrC#N ATDGTVJJHBUTRL-UHFFFAOYSA-N 0.000 description 2
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- 238000002474 experimental method Methods 0.000 description 2
- 230000002538 fungal effect Effects 0.000 description 2
- 150000002431 hydrogen Chemical group 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 235000010755 mineral Nutrition 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 229910052763 palladium Inorganic materials 0.000 description 2
- 239000003209 petroleum derivative Substances 0.000 description 2
- DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 description 2
- 229940117953 phenylisothiocyanate Drugs 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- 229910052903 pyrophyllite Inorganic materials 0.000 description 2
- UCFSULAKAYDAAE-UHFFFAOYSA-N quinolin-1-ium;iodide Chemical compound I.N1=CC=CC2=CC=CC=C21 UCFSULAKAYDAAE-UHFFFAOYSA-N 0.000 description 2
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 2
- 238000005507 spraying Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 239000000454 talc Substances 0.000 description 2
- 229910052623 talc Inorganic materials 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 238000004809 thin layer chromatography Methods 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical class OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 description 1
- HDPNBNXLBDFELL-UHFFFAOYSA-N 1,1,1-trimethoxyethane Chemical compound COC(C)(OC)OC HDPNBNXLBDFELL-UHFFFAOYSA-N 0.000 description 1
- UZKVTJNMCRNIDU-UHFFFAOYSA-N 1,5-dimethyl-[1,2,4]triazolo[4,3-a]quinoline Chemical compound C1=CC=C2N3C(C)=NN=C3C=C(C)C2=C1 UZKVTJNMCRNIDU-UHFFFAOYSA-N 0.000 description 1
- XUKLOXWWXUJYQW-UHFFFAOYSA-N 1-(ethoxymethyl)-9-methyl-[1,2,4]triazolo[4,3-a]quinoline Chemical compound C1=CC(C)=C2N3C(COCC)=NN=C3C=CC2=C1 XUKLOXWWXUJYQW-UHFFFAOYSA-N 0.000 description 1
- ZELWIQYBMGMRNA-UHFFFAOYSA-N 1-(ethoxymethyl)-[1,2,4]triazolo[4,3-a]quinoline Chemical compound C1=CC=C2N3C(COCC)=NN=C3C=CC2=C1 ZELWIQYBMGMRNA-UHFFFAOYSA-N 0.000 description 1
- JRJWVUCRJNVQLB-UHFFFAOYSA-N 1-butyl-[1,2,4]triazolo[4,3-a]quinoline Chemical compound C1=CC=C2N3C(CCCC)=NN=C3C=CC2=C1 JRJWVUCRJNVQLB-UHFFFAOYSA-N 0.000 description 1
- KFMBSEHDGBEPAO-UHFFFAOYSA-N 1-ethyl-5-methyl-[1,2,4]triazolo[4,3-a]quinoline Chemical compound C1=CC=C2N3C(CC)=NN=C3C=C(C)C2=C1 KFMBSEHDGBEPAO-UHFFFAOYSA-N 0.000 description 1
- RMHVIIGTGXZZTR-UHFFFAOYSA-N 1-ethyl-[1,2,4]triazolo[4,3-a]quinoline Chemical compound C1=CC=C2N3C(CC)=NN=C3C=CC2=C1 RMHVIIGTGXZZTR-UHFFFAOYSA-N 0.000 description 1
- QTODCAWXQQKXRL-UHFFFAOYSA-N 1-hydroxy-2h-quinoline Chemical compound C1=CC=C2N(O)CC=CC2=C1 QTODCAWXQQKXRL-UHFFFAOYSA-N 0.000 description 1
- VYRUZHMGBQXYTF-UHFFFAOYSA-N 1-methyl-[1,2,4]triazolo[4,3-a]quinoline Chemical compound C1=CC=C2N3C(C)=NN=C3C=CC2=C1 VYRUZHMGBQXYTF-UHFFFAOYSA-N 0.000 description 1
- PEBLUEAPMDGFRE-UHFFFAOYSA-N 1-sulfanyl-2h-quinoline Chemical compound C1=CC=C2N(S)CC=CC2=C1 PEBLUEAPMDGFRE-UHFFFAOYSA-N 0.000 description 1
- ALWNZLDVOJPJOZ-UHFFFAOYSA-N 2,2,2-trifluoro-n'-quinolin-2-ylacetohydrazide Chemical compound C1=CC=CC2=NC(NNC(=O)C(F)(F)F)=CC=C21 ALWNZLDVOJPJOZ-UHFFFAOYSA-N 0.000 description 1
- QNBJYUUUYZVIJP-UHFFFAOYSA-N 2,4-dichloroquinoline Chemical compound C1=CC=CC2=NC(Cl)=CC(Cl)=C21 QNBJYUUUYZVIJP-UHFFFAOYSA-N 0.000 description 1
- XZBIMVJBMOHAEL-UHFFFAOYSA-N 2-([1,2,4]triazolo[4,3-a]quinolin-1-yl)ethanol Chemical compound C1=CC=C2N3C(CCO)=NN=C3C=CC2=C1 XZBIMVJBMOHAEL-UHFFFAOYSA-N 0.000 description 1
- OFUFXTHGZWIDDB-UHFFFAOYSA-N 2-chloroquinoline Chemical compound C1=CC=CC2=NC(Cl)=CC=C21 OFUFXTHGZWIDDB-UHFFFAOYSA-N 0.000 description 1
- OGRIQXCIIAIROA-UHFFFAOYSA-N 2h-[1,2,4]triazolo[4,3-a]quinolin-1-one Chemical compound C1=CC=C2N3C(=O)NN=C3C=CC2=C1 OGRIQXCIIAIROA-UHFFFAOYSA-N 0.000 description 1
- WZQDSHZMIONMBH-UHFFFAOYSA-N 2h-quinoline-1-carboxamide Chemical compound C1=CC=C2N(C(=O)N)CC=CC2=C1 WZQDSHZMIONMBH-UHFFFAOYSA-N 0.000 description 1
- DNNVRTZJRKIUFK-UHFFFAOYSA-N 3,4-dihydroquinoline Chemical compound C1=CC=C2N=CCCC2=C1 DNNVRTZJRKIUFK-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- JRXXEXVXTFEBIY-UHFFFAOYSA-N 3-ethoxypropanoic acid Chemical compound CCOCCC(O)=O JRXXEXVXTFEBIY-UHFFFAOYSA-N 0.000 description 1
- SJRAPMSVYVMTES-UHFFFAOYSA-N 4-chloro-5-methyl-[1,2,4]triazolo[4,3-a]quinoline Chemical compound C1=CC=C2C(C)=C(Cl)C3=NN=CN3C2=C1 SJRAPMSVYVMTES-UHFFFAOYSA-N 0.000 description 1
- JTXSYUXQRJAHPZ-UHFFFAOYSA-N 5,7,9-trimethyl-[1,2,4]triazolo[4,3-a]quinoline Chemical compound CC1=CC2=NN=CN2C2=C(C)C=C(C)C=C21 JTXSYUXQRJAHPZ-UHFFFAOYSA-N 0.000 description 1
- FZXOGGSJPLANKT-UHFFFAOYSA-N 5,8-dimethyl-[1,2,4]triazolo[4,3-a]quinoline Chemical compound CC1=CC2=NN=CN2C2=CC(C)=CC=C21 FZXOGGSJPLANKT-UHFFFAOYSA-N 0.000 description 1
- LZLLSBLESSGUMJ-UHFFFAOYSA-N 5-chloro-4-methyl-[1,2,4]triazolo[4,3-a]quinoline Chemical compound CC1=C(Cl)C2=CC=CC=C2N2C1=NN=C2 LZLLSBLESSGUMJ-UHFFFAOYSA-N 0.000 description 1
- VPUMZLVLKCMKFQ-UHFFFAOYSA-N 5-methyl-2h-[1,2,4]triazolo[4,3-a]quinolin-1-one Chemical compound C1=CC=C2C(C)=CC3=NN=C(O)N3C2=C1 VPUMZLVLKCMKFQ-UHFFFAOYSA-N 0.000 description 1
- VSUPYSJUZGXREB-UHFFFAOYSA-N 5-methyl-2h-[1,2,4]triazolo[4,3-a]quinoline-1-thione Chemical compound C1=CC=C2C(C)=CC3=NNC(=S)N3C2=C1 VSUPYSJUZGXREB-UHFFFAOYSA-N 0.000 description 1
- FTNVDGUZYLOBSQ-UHFFFAOYSA-N 5-methyl-[1,2,4]triazolo[4,3-a]quinoline Chemical compound C1=CC=C2C(C)=CC3=NN=CN3C2=C1 FTNVDGUZYLOBSQ-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- VBUFVNKVPOCHAG-UHFFFAOYSA-N 9-methyl-4,5-dihydro-[1,2,4]triazolo[4,3-a]quinoline Chemical compound C1CC2=NN=CN2C2=C1C=CC=C2C VBUFVNKVPOCHAG-UHFFFAOYSA-N 0.000 description 1
- 235000001674 Agaricus brunnescens Nutrition 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- 239000004342 Benzoyl peroxide Substances 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 241000221787 Erysiphe Species 0.000 description 1
- 238000005967 Finkelstein reaction Methods 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 241000238631 Hexapoda Species 0.000 description 1
- LOMVENUNSWAXEN-UHFFFAOYSA-N Methyl oxalate Chemical compound COC(=O)C(=O)OC LOMVENUNSWAXEN-UHFFFAOYSA-N 0.000 description 1
- VKEQBMCRQDSRET-UHFFFAOYSA-N Methylone Chemical compound CNC(C)C(=O)C1=CC=C2OCOC2=C1 VKEQBMCRQDSRET-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 229920003171 Poly (ethylene oxide) Chemical class 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- RNAAPNHFQFPIRT-UHFFFAOYSA-N [1,2,4]triazolo[4,3-a]quinolin-1-amine;hydrobromide Chemical compound Br.C1=CC=C2N3C(N)=NN=C3C=CC2=C1 RNAAPNHFQFPIRT-UHFFFAOYSA-N 0.000 description 1
- MXPZAKWKTBEYFK-UHFFFAOYSA-N [1,2,4]triazolo[4,3-a]quinolin-1-ylmethanamine Chemical compound C1=CC=C2N3C(CN)=NN=C3C=CC2=C1 MXPZAKWKTBEYFK-UHFFFAOYSA-N 0.000 description 1
- GBVLWNJLPZJFBZ-UHFFFAOYSA-N [1,2,4]triazolo[4,3-a]quinoline-1-carboxylic acid Chemical compound C1=CC=C2N3C(C(=O)O)=NN=C3C=CC2=C1 GBVLWNJLPZJFBZ-UHFFFAOYSA-N 0.000 description 1
- VJYXYXIEJCACPV-UHFFFAOYSA-N [1,2,4]triazolo[4,3-a]quinoline;hydrochloride Chemical compound Cl.C1=CC=C2N3C=NN=C3C=CC2=C1 VJYXYXIEJCACPV-UHFFFAOYSA-N 0.000 description 1
- CCYGIUKMRPMJRS-UHFFFAOYSA-N [Cl].Br Chemical compound [Cl].Br CCYGIUKMRPMJRS-UHFFFAOYSA-N 0.000 description 1
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 238000005273 aeration Methods 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 125000004414 alkyl thio group Chemical group 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 230000009435 amidation Effects 0.000 description 1
- 238000007112 amidation reaction Methods 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 238000007098 aminolysis reaction Methods 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 229960000892 attapulgite Drugs 0.000 description 1
- 239000000440 bentonite Substances 0.000 description 1
- 229910000278 bentonite Inorganic materials 0.000 description 1
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
- 235000013532 brandy Nutrition 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
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Inorganic materials [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 1
- ZOMBKNNSYQHRCA-UHFFFAOYSA-J calcium sulfate hemihydrate Chemical compound O.[Ca+2].[Ca+2].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O ZOMBKNNSYQHRCA-UHFFFAOYSA-J 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000006114 decarboxylation reaction Methods 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 238000006704 dehydrohalogenation reaction Methods 0.000 description 1
- WYACBZDAHNBPPB-UHFFFAOYSA-N diethyl oxalate Chemical compound CCOC(=O)C(=O)OCC WYACBZDAHNBPPB-UHFFFAOYSA-N 0.000 description 1
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical class C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 239000004495 emulsifiable concentrate Substances 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- XZBIXDPGRMLSTC-UHFFFAOYSA-N formohydrazide Chemical compound NNC=O XZBIXDPGRMLSTC-UHFFFAOYSA-N 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000010440 gypsum Substances 0.000 description 1
- 229910052602 gypsum Inorganic materials 0.000 description 1
- 239000011507 gypsum plaster Substances 0.000 description 1
- 125000004969 haloethyl group Chemical group 0.000 description 1
- 150000002366 halogen compounds Chemical class 0.000 description 1
- 230000002140 halogenating effect Effects 0.000 description 1
- 230000026030 halogenation Effects 0.000 description 1
- 238000005658 halogenation reaction Methods 0.000 description 1
- 239000003864 humus Substances 0.000 description 1
- 150000002429 hydrazines Chemical class 0.000 description 1
- 125000000717 hydrazino group Chemical group [H]N([*])N([H])[H] 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- ZMZDMBWJUHKJPS-UHFFFAOYSA-N hydrogen thiocyanate Natural products SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 description 1
- 229940071870 hydroiodic acid Drugs 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000002054 inoculum Substances 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 239000012669 liquid formulation Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- VWZIOEQMYKGSMO-UHFFFAOYSA-N n-([1,2,4]triazolo[4,3-a]quinolin-1-yl)acetamide Chemical compound C1=CC=C2N3C(NC(=O)C)=NN=C3C=CC2=C1 VWZIOEQMYKGSMO-UHFFFAOYSA-N 0.000 description 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 1
- HBXQPTFAIGLBLS-UHFFFAOYSA-N n-methyl-[1,2,4]triazolo[4,3-a]quinolin-1-amine Chemical compound C1=CC=C2N3C(NC)=NN=C3C=CC2=C1 HBXQPTFAIGLBLS-UHFFFAOYSA-N 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 229910000510 noble metal Inorganic materials 0.000 description 1
- 231100001184 nonphytotoxic Toxicity 0.000 description 1
- 235000015205 orange juice Nutrition 0.000 description 1
- 150000002905 orthoesters Chemical class 0.000 description 1
- 229910052625 palygorskite Inorganic materials 0.000 description 1
- 230000001717 pathogenic effect Effects 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 244000000003 plant pathogen Species 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 150000007519 polyprotic acids Polymers 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 239000001965 potato dextrose agar Substances 0.000 description 1
- 238000004382 potting Methods 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000012264 purified product Substances 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 150000003248 quinolines Chemical class 0.000 description 1
- 238000006798 ring closing metathesis reaction Methods 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- ATRAZFPRHYFKRL-UHFFFAOYSA-M sodium [1,2,4]triazolo[4,3-a]quinoline-1-carboxylate Chemical compound [Na+].C1=CC=C2N3C(C(=O)[O-])=NN=C3C=CC2=C1 ATRAZFPRHYFKRL-UHFFFAOYSA-M 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 239000002195 soluble material Substances 0.000 description 1
- 238000001256 steam distillation Methods 0.000 description 1
- 239000008223 sterile water Substances 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 239000008399 tap water Substances 0.000 description 1
- 235000020679 tap water Nutrition 0.000 description 1
- 150000003567 thiocyanates Chemical class 0.000 description 1
- 239000010455 vermiculite Substances 0.000 description 1
- 229910052902 vermiculite Inorganic materials 0.000 description 1
- 235000019354 vermiculite Nutrition 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom 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
- C07D215/38—Nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- 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
- A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
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)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US17231771A | 1971-08-16 | 1971-08-16 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2239892A1 true DE2239892A1 (de) | 1973-03-01 |
Family
ID=22627199
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2239892A Withdrawn DE2239892A1 (de) | 1971-08-16 | 1972-08-14 | Mittel zur bekaempfung von pflanzenpathogenen organismen |
Country Status (31)
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU510985B2 (en) * | 1977-03-29 | 1980-07-24 | Capsugel A.G. | Liquid filled capsule |
| JPS61186648U (enrdf_load_stackoverflow) * | 1984-12-29 | 1986-11-20 | ||
| AT393764B (de) * | 1986-09-02 | 1991-12-10 | System Elektrotechnik Gotthold | Starthilfekabel |
| JPS63166228U (enrdf_load_stackoverflow) * | 1987-04-21 | 1988-10-28 | ||
| US7358259B2 (en) | 2003-09-26 | 2008-04-15 | Rigel Pharmaceuticals, Inc. | HCV inhibitors and methods of using them |
| WO2005121138A2 (en) * | 2004-06-03 | 2005-12-22 | Rigel Pharmaceuticals, Inc. | Heterotricyclic compounds for use as hcv inhibitors |
| EP1978966A4 (en) * | 2006-01-23 | 2010-11-10 | Amira Pharmaceuticals Inc | TRICYCLIC INHIBITORS OF 5-LIPOXYGENASE |
-
0
- BE BE787536D patent/BE787536A/xx not_active IP Right Cessation
-
1971
- 1971-08-16 ES ES405899A patent/ES405899A1/es not_active Expired
-
1972
- 1972-08-04 ZA ZA725365A patent/ZA725365B/xx unknown
- 1972-08-07 IL IL40060A patent/IL40060A/en unknown
- 1972-08-09 YU YU2043/72A patent/YU36937B/xx unknown
- 1972-08-09 AU AU45397/72A patent/AU461057B2/en not_active Expired
- 1972-08-10 CA CA149,119A patent/CA997766A/en not_active Expired
- 1972-08-10 NL NLAANVRAGE7210957,A patent/NL177173C/xx not_active IP Right Cessation
- 1972-08-12 IT IT52168/72A patent/IT962096B/it active
- 1972-08-14 PL PL1972157263A patent/PL94442B1/pl unknown
- 1972-08-14 GT GT197225694A patent/GT197225694A/es unknown
- 1972-08-14 IE IE1125/72A patent/IE36916B1/xx unknown
- 1972-08-14 KR KR7201228A patent/KR790000421B1/ko not_active Expired
- 1972-08-14 DE DE2239892A patent/DE2239892A1/de not_active Withdrawn
- 1972-08-15 GB GB3798972A patent/GB1374369A/en not_active Expired
- 1972-08-15 CH CH1209772A patent/CH552942A/fr not_active IP Right Cessation
- 1972-08-15 HU HU72EI427A patent/HU167272B/hu unknown
- 1972-08-15 CH CH411774A patent/CH564016A5/xx not_active IP Right Cessation
- 1972-08-15 SE SE7210551A patent/SE405313B/xx unknown
- 1972-08-15 CS CS725667A patent/CS190371B2/cs unknown
- 1972-08-15 EG EG335/72A patent/EG10668A/xx active
- 1972-08-15 DK DK402572AA patent/DK139832B/da not_active IP Right Cessation
- 1972-08-16 AT AT704672A patent/AT324767B/de not_active IP Right Cessation
- 1972-08-16 FR FR7229270A patent/FR2149467B1/fr not_active Expired
- 1972-08-16 BG BG024103A patent/BG20354A3/xx unknown
- 1972-08-16 BG BG024104D patent/BG24409A3/xx unknown
- 1972-08-16 DD DD173662*A patent/DD107462A5/xx unknown
- 1972-08-16 RO RO7282499A patent/RO79165A/ro unknown
- 1972-08-16 RO RO197271972A patent/RO63409A/ro unknown
- 1972-08-16 AR AR243610A patent/AR195289A1/es active
- 1972-08-16 DD DD165089A patent/DD104176A5/xx unknown
- 1972-08-16 PH PH13806A patent/PH10204A/en unknown
- 1972-08-16 BG BG21209A patent/BG19623A1/xx unknown
- 1972-08-16 JP JP47082060A patent/JPS5760321B2/ja not_active Expired
-
1973
- 1973-03-15 SU SU1895868A patent/SU554815A3/ru active
- 1973-05-04 AR AR247862A patent/AR215825A1/es active
-
1975
- 1975-06-27 SE SE7507384A patent/SE422059B/xx not_active IP Right Cessation
-
1978
- 1978-12-30 MY MY200/78A patent/MY7800200A/xx unknown
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