CA1060017A - 3-alkoxy-benzo-1,2,4-triazines, process for their preparation and their use as fungicides and bactericides - Google Patents
3-alkoxy-benzo-1,2,4-triazines, process for their preparation and their use as fungicides and bactericidesInfo
- Publication number
- CA1060017A CA1060017A CA259,907A CA259907A CA1060017A CA 1060017 A CA1060017 A CA 1060017A CA 259907 A CA259907 A CA 259907A CA 1060017 A CA1060017 A CA 1060017A
- Authority
- CA
- Canada
- Prior art keywords
- benzo
- compound according
- triazine
- alkoxy
- chlorine
- 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.)
- Expired
Links
- 238000000034 method Methods 0.000 title claims description 20
- 230000000844 anti-bacterial effect Effects 0.000 title abstract description 4
- 238000002360 preparation method Methods 0.000 title description 16
- 239000000417 fungicide Substances 0.000 title description 3
- 239000003899 bactericide agent Substances 0.000 title description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 12
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 11
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 7
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 5
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 4
- 150000001875 compounds Chemical class 0.000 claims description 69
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 31
- 239000000460 chlorine Substances 0.000 claims description 28
- 241000233866 Fungi Species 0.000 claims description 14
- 239000000203 mixture Substances 0.000 claims description 14
- 229910052801 chlorine Inorganic materials 0.000 claims description 12
- 239000003085 diluting agent Substances 0.000 claims description 12
- 241000607479 Yersinia pestis Species 0.000 claims description 10
- 229910052751 metal Inorganic materials 0.000 claims description 9
- 239000002184 metal Substances 0.000 claims description 9
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- 239000002689 soil Substances 0.000 claims description 8
- 239000011230 binding agent Substances 0.000 claims description 7
- 239000003638 chemical reducing agent Substances 0.000 claims description 7
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 6
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 6
- 229910052794 bromium Inorganic materials 0.000 claims description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 5
- 239000004480 active ingredient Substances 0.000 claims description 5
- 150000002367 halogens Chemical group 0.000 claims description 5
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 239000007800 oxidant agent Substances 0.000 claims description 2
- 230000003647 oxidation Effects 0.000 claims description 2
- 238000007254 oxidation reaction Methods 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- 229940124024 weight reducing agent Drugs 0.000 claims 1
- 230000000855 fungicidal effect Effects 0.000 abstract description 4
- 230000000895 acaricidal effect Effects 0.000 abstract description 3
- 230000000749 insecticidal effect Effects 0.000 abstract description 2
- 125000005843 halogen group Chemical group 0.000 abstract 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 19
- 241000196324 Embryophyta Species 0.000 description 17
- 238000006243 chemical reaction Methods 0.000 description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 13
- -1 phenylene radical Chemical class 0.000 description 13
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 239000002253 acid Substances 0.000 description 9
- 238000002844 melting Methods 0.000 description 9
- 230000008018 melting Effects 0.000 description 9
- GGZDOSFUDVOCBS-UHFFFAOYSA-N 3-chloro-1,2,4-benzotriazine Chemical compound C1=CC=CC2=NC(Cl)=NN=C21 GGZDOSFUDVOCBS-UHFFFAOYSA-N 0.000 description 8
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 8
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 8
- 235000015097 nutrients Nutrition 0.000 description 8
- 239000003795 chemical substances by application Substances 0.000 description 7
- 239000007858 starting material Substances 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- 241000894006 Bacteria Species 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- 150000001298 alcohols Chemical class 0.000 description 6
- 208000015181 infectious disease Diseases 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
- 235000013339 cereals Nutrition 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- LHDZLYASAVFIJM-UHFFFAOYSA-N 3,7-dichloro-1,2,4-benzotriazine Chemical compound N1=C(Cl)N=NC2=CC(Cl)=CC=C21 LHDZLYASAVFIJM-UHFFFAOYSA-N 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- 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 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 4
- 235000019270 ammonium chloride Nutrition 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 239000003995 emulsifying agent Substances 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 239000011877 solvent mixture Substances 0.000 description 4
- 241000894007 species Species 0.000 description 4
- 239000007921 spray Substances 0.000 description 4
- FSUAEHJACMGVCR-UHFFFAOYSA-N 7-chloro-3-methoxy-1,2,4-benzotriazine Chemical compound C1=C(Cl)C=CC2=NC(OC)=NN=C21 FSUAEHJACMGVCR-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 229920001817 Agar Polymers 0.000 description 3
- 240000005979 Hordeum vulgare Species 0.000 description 3
- 235000007340 Hordeum vulgare Nutrition 0.000 description 3
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 3
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 3
- 235000010419 agar Nutrition 0.000 description 3
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 3
- 125000002877 alkyl aryl group Chemical group 0.000 description 3
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 3
- 150000001555 benzenes Chemical class 0.000 description 3
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 3
- 150000001721 carbon Chemical group 0.000 description 3
- 239000000969 carrier Substances 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 description 3
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 3
- 201000010099 disease Diseases 0.000 description 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 3
- YAGKRVSRTSUGEY-UHFFFAOYSA-N ferricyanide Chemical compound [Fe+3].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-] YAGKRVSRTSUGEY-UHFFFAOYSA-N 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 229910052500 inorganic mineral Inorganic materials 0.000 description 3
- 150000002500 ions Chemical class 0.000 description 3
- 239000011707 mineral Substances 0.000 description 3
- 235000010755 mineral Nutrition 0.000 description 3
- 230000017066 negative regulation of growth Effects 0.000 description 3
- KPSSIOMAKSHJJG-UHFFFAOYSA-N neopentyl alcohol Chemical compound CC(C)(C)CO KPSSIOMAKSHJJG-UHFFFAOYSA-N 0.000 description 3
- 210000004940 nucleus Anatomy 0.000 description 3
- 244000052769 pathogen Species 0.000 description 3
- 229920000151 polyglycol Polymers 0.000 description 3
- 239000010695 polyglycol Substances 0.000 description 3
- 239000002243 precursor Substances 0.000 description 3
- 230000001681 protective effect Effects 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- FHPVCEPQUZAPIJ-UHFFFAOYSA-N 3-butoxy-7-chloro-1,2,4-benzotriazine Chemical compound C1=C(Cl)C=CC2=NC(OCCCC)=NN=C21 FHPVCEPQUZAPIJ-UHFFFAOYSA-N 0.000 description 2
- YXKCIEQPVVUHJS-UHFFFAOYSA-N 3-chloro-1-oxido-1,2,4-benzotriazin-1-ium Chemical compound C1=CC=C2[N+]([O-])=NC(Cl)=NC2=C1 YXKCIEQPVVUHJS-UHFFFAOYSA-N 0.000 description 2
- HNVRRHSXBLFLIG-UHFFFAOYSA-N 3-hydroxy-3-methylbut-1-ene Chemical compound CC(C)(O)C=C HNVRRHSXBLFLIG-UHFFFAOYSA-N 0.000 description 2
- YAMDNQFVYVEAGY-UHFFFAOYSA-N 3-methoxy-7-(trifluoromethyl)-1,2,4-benzotriazine Chemical compound C1=C(C(F)(F)F)C=CC2=NC(OC)=NN=C21 YAMDNQFVYVEAGY-UHFFFAOYSA-N 0.000 description 2
- ZTSVECRXNYNSKX-UHFFFAOYSA-N 7-chloro-3-ethoxy-1,2,4-benzotriazine Chemical compound C1=C(Cl)C=CC2=NC(OCC)=NN=C21 ZTSVECRXNYNSKX-UHFFFAOYSA-N 0.000 description 2
- MJYSPVJBDGDKHL-UHFFFAOYSA-N 7-chloro-3-hexoxy-1,2,4-benzotriazine Chemical compound C1=C(Cl)C=CC2=NC(OCCCCCC)=NN=C21 MJYSPVJBDGDKHL-UHFFFAOYSA-N 0.000 description 2
- PMHSZOVGQRDOSS-UHFFFAOYSA-N 7-chloro-3-methoxy-1-oxido-1,2,4-benzotriazin-1-ium Chemical compound C1=C(Cl)C=CC2=NC(OC)=N[N+]([O-])=C21 PMHSZOVGQRDOSS-UHFFFAOYSA-N 0.000 description 2
- LNDVDYSZUKILKC-UHFFFAOYSA-N 7-chloro-3-propan-2-yloxy-1,2,4-benzotriazine Chemical compound C1=C(Cl)C=CC2=NC(OC(C)C)=NN=C21 LNDVDYSZUKILKC-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- HNUALPPJLMYHDK-UHFFFAOYSA-N C[CH]C Chemical compound C[CH]C HNUALPPJLMYHDK-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- 239000004606 Fillers/Extenders Substances 0.000 description 2
- 206010017533 Fungal infection Diseases 0.000 description 2
- 240000007594 Oryza sativa Species 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- 241000228453 Pyrenophora Species 0.000 description 2
- 239000007868 Raney catalyst Substances 0.000 description 2
- 229910000564 Raney nickel Inorganic materials 0.000 description 2
- 241001361634 Rhizoctonia Species 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 241000209140 Triticum Species 0.000 description 2
- 241000589634 Xanthomonas Species 0.000 description 2
- 241000589652 Xanthomonas oryzae Species 0.000 description 2
- 229960000583 acetic acid Drugs 0.000 description 2
- 239000008272 agar Substances 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- ZCCIPPOKBCJFDN-UHFFFAOYSA-N calcium nitrate Chemical compound [Ca+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O ZCCIPPOKBCJFDN-UHFFFAOYSA-N 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 239000000470 constituent Substances 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 208000024386 fungal infectious disease Diseases 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
- 238000005984 hydrogenation reaction Methods 0.000 description 2
- 238000011081 inoculation Methods 0.000 description 2
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- HCTVWSOKIJULET-LQDWTQKMSA-M phenoxymethylpenicillin potassium Chemical compound [K+].N([C@H]1[C@H]2SC([C@@H](N2C1=O)C([O-])=O)(C)C)C(=O)COC1=CC=CC=C1 HCTVWSOKIJULET-LQDWTQKMSA-M 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
- NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000011814 protection agent Substances 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 235000012239 silicon dioxide Nutrition 0.000 description 2
- 239000004094 surface-active agent Substances 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
- 239000011701 zinc Substances 0.000 description 2
- FYADHXFMURLYQI-UHFFFAOYSA-N 1,2,4-triazine Chemical compound C1=CN=NC=N1 FYADHXFMURLYQI-UHFFFAOYSA-N 0.000 description 1
- BMSGNGPCJCDOGE-UHFFFAOYSA-N 1,2-dihydro-1,2,4-benzotriazin-3-amine Chemical class C1=CC=C2NNC(N)=NC2=C1 BMSGNGPCJCDOGE-UHFFFAOYSA-N 0.000 description 1
- DEWLEGDTCGBNGU-UHFFFAOYSA-N 1,3-dichloropropan-2-ol Chemical compound ClCC(O)CCl DEWLEGDTCGBNGU-UHFFFAOYSA-N 0.000 description 1
- YYTSGNJTASLUOY-UHFFFAOYSA-N 1-chloropropan-2-ol Chemical compound CC(O)CCl YYTSGNJTASLUOY-UHFFFAOYSA-N 0.000 description 1
- KPWDGTGXUYRARH-UHFFFAOYSA-N 2,2,2-trichloroethanol Chemical compound OCC(Cl)(Cl)Cl KPWDGTGXUYRARH-UHFFFAOYSA-N 0.000 description 1
- QWVCIORZLNBIIC-UHFFFAOYSA-N 2,3-dibromopropan-1-ol Chemical compound OCC(Br)CBr QWVCIORZLNBIIC-UHFFFAOYSA-N 0.000 description 1
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 1
- SZIFAVKTNFCBPC-UHFFFAOYSA-N 2-chloroethanol Chemical compound OCCCl SZIFAVKTNFCBPC-UHFFFAOYSA-N 0.000 description 1
- TZYRSLHNPKPEFV-UHFFFAOYSA-N 2-ethyl-1-butanol Chemical compound CCC(CC)CO TZYRSLHNPKPEFV-UHFFFAOYSA-N 0.000 description 1
- KEKCQXQAPNKMLX-UHFFFAOYSA-N 2h-1,2,4-benzotriazin-3-one Chemical compound C1=CC=CC2=NC(O)=NN=C21 KEKCQXQAPNKMLX-UHFFFAOYSA-N 0.000 description 1
- ZMSWTQQQVGHRRJ-UHFFFAOYSA-N 3,7-dichloro-1-oxido-1,2,4-benzotriazin-1-ium Chemical compound C1=C(Cl)C=C2[N+]([O-])=NC(Cl)=NC2=C1 ZMSWTQQQVGHRRJ-UHFFFAOYSA-N 0.000 description 1
- HOFIOKVVXPJUCT-UHFFFAOYSA-N 3-(2-butoxyethoxy)-7-chloro-1,2,4-benzotriazine Chemical compound C1=C(Cl)C=CC2=NC(OCCOCCCC)=NN=C21 HOFIOKVVXPJUCT-UHFFFAOYSA-N 0.000 description 1
- YYLROBYBOMFSCW-UHFFFAOYSA-N 3-bromo-7-chloro-1,2,4-benzotriazine Chemical compound N1=C(Br)N=NC2=CC(Cl)=CC=C21 YYLROBYBOMFSCW-UHFFFAOYSA-N 0.000 description 1
- VMZDTMXGANHCJG-UHFFFAOYSA-N 3-butoxy-1-oxido-1,2,4-benzotriazin-1-ium Chemical class C1=CC=CC2=NC(OCCCC)=N[N+]([O-])=C21 VMZDTMXGANHCJG-UHFFFAOYSA-N 0.000 description 1
- GVQHXCDXIOKTLZ-UHFFFAOYSA-N 3-chloro-7-iodo-1,2,4-benzotriazine Chemical compound C1=C(I)C=CC2=NC(Cl)=NN=C21 GVQHXCDXIOKTLZ-UHFFFAOYSA-N 0.000 description 1
- XFDZFWVOYSVYQM-UHFFFAOYSA-N 3-chloro-7-methoxy-1,2,4-benzotriazine Chemical compound N1=C(Cl)N=NC2=CC(OC)=CC=C21 XFDZFWVOYSVYQM-UHFFFAOYSA-N 0.000 description 1
- YCIBGTILPFGMDJ-UHFFFAOYSA-N 3-methoxy-1,2,4-benzotriazine Chemical compound C1=CC=CC2=NC(OC)=NN=C21 YCIBGTILPFGMDJ-UHFFFAOYSA-N 0.000 description 1
- JDFDHBSESGTDAL-UHFFFAOYSA-N 3-methoxypropan-1-ol Chemical compound COCCCO JDFDHBSESGTDAL-UHFFFAOYSA-N 0.000 description 1
- WVYWICLMDOOCFB-UHFFFAOYSA-N 4-methyl-2-pentanol Chemical compound CC(C)CC(C)O WVYWICLMDOOCFB-UHFFFAOYSA-N 0.000 description 1
- UHPMCKVQTMMPCG-UHFFFAOYSA-N 5,8-dihydroxy-2-methoxy-6-methyl-7-(2-oxopropyl)naphthalene-1,4-dione Chemical compound CC1=C(CC(C)=O)C(O)=C2C(=O)C(OC)=CC(=O)C2=C1O UHPMCKVQTMMPCG-UHFFFAOYSA-N 0.000 description 1
- IOLMTUDDZOMITO-UHFFFAOYSA-N 7-bromo-1-oxido-3-propan-2-yloxy-1,2,4-benzotriazin-1-ium Chemical compound C1=C(Br)C=CC2=NC(OC(C)C)=N[N+]([O-])=C21 IOLMTUDDZOMITO-UHFFFAOYSA-N 0.000 description 1
- GIAKYOSVEURTRX-UHFFFAOYSA-N 7-bromo-3-chloro-1,2,4-benzotriazine Chemical compound C1=C(Br)C=CC2=NC(Cl)=NN=C21 GIAKYOSVEURTRX-UHFFFAOYSA-N 0.000 description 1
- MVXRXNJUMHSGLO-UHFFFAOYSA-N 7-bromo-3-methoxy-1,2,4-benzotriazine Chemical compound C1=C(Br)C=CC2=NC(OC)=NN=C21 MVXRXNJUMHSGLO-UHFFFAOYSA-N 0.000 description 1
- KZKLVPLSFVQKIX-UHFFFAOYSA-N 7-chloro-3-propoxy-1,2,4-benzotriazine Chemical compound C1=C(Cl)C=CC2=NC(OCCC)=NN=C21 KZKLVPLSFVQKIX-UHFFFAOYSA-N 0.000 description 1
- 108010088751 Albumins Proteins 0.000 description 1
- 102000009027 Albumins Human genes 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 241000371644 Curvularia ravenelii Species 0.000 description 1
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 1
- YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 1
- 241000223218 Fusarium Species 0.000 description 1
- 241000206672 Gelidium Species 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- GXCLVBGFBYZDAG-UHFFFAOYSA-N N-[2-(1H-indol-3-yl)ethyl]-N-methylprop-2-en-1-amine Chemical compound CN(CCC1=CNC2=C1C=CC=C2)CC=C GXCLVBGFBYZDAG-UHFFFAOYSA-N 0.000 description 1
- 241000233654 Oomycetes Species 0.000 description 1
- 239000001888 Peptone Substances 0.000 description 1
- 108010080698 Peptones Proteins 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 241000589516 Pseudomonas Species 0.000 description 1
- 241000221300 Puccinia Species 0.000 description 1
- 241001123569 Puccinia recondita Species 0.000 description 1
- 241000231139 Pyricularia Species 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
- 240000001987 Pyrus communis Species 0.000 description 1
- 206010037888 Rash pustular Diseases 0.000 description 1
- 241000212342 Sium Species 0.000 description 1
- 244000061456 Solanum tuberosum Species 0.000 description 1
- 235000002595 Solanum tuberosum Nutrition 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
- 241000567019 Xanthomonas vesicatoria Species 0.000 description 1
- OCBFFGCSTGGPSQ-UHFFFAOYSA-N [CH2]CC Chemical compound [CH2]CC OCBFFGCSTGGPSQ-UHFFFAOYSA-N 0.000 description 1
- 239000000642 acaricide Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
- 229910000102 alkali metal hydride Inorganic materials 0.000 description 1
- 150000008046 alkali metal hydrides Chemical class 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 229960000892 attapulgite Drugs 0.000 description 1
- 230000031018 biological processes and functions Effects 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 229940126214 compound 3 Drugs 0.000 description 1
- 239000008121 dextrose Substances 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
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 229960001760 dimethyl sulfoxide Drugs 0.000 description 1
- 235000021186 dishes Nutrition 0.000 description 1
- BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 description 1
- 238000010410 dusting Methods 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
- 230000035784 germination Effects 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 230000002363 herbicidal effect Effects 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- PHTQWCKDNZKARW-UHFFFAOYSA-N isoamylol Chemical compound CC(C)CCO PHTQWCKDNZKARW-UHFFFAOYSA-N 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
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000013028 medium composition Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 229910052901 montmorillonite Inorganic materials 0.000 description 1
- UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene-acid Natural products C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 1
- 230000001069 nematicidal effect Effects 0.000 description 1
- 239000005645 nematicide Substances 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 229910052625 palygorskite Inorganic materials 0.000 description 1
- 230000003071 parasitic effect Effects 0.000 description 1
- 239000006072 paste Substances 0.000 description 1
- 230000001717 pathogenic effect Effects 0.000 description 1
- 235000019319 peptone Nutrition 0.000 description 1
- 238000003359 percent control normalization Methods 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 235000014786 phosphorus Nutrition 0.000 description 1
- 230000003032 phytopathogenic effect Effects 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 239000011698 potassium fluoride Substances 0.000 description 1
- 235000003270 potassium fluoride Nutrition 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 208000029561 pustule Diseases 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 150000003738 xylenes Chemical class 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D253/00—Heterocyclic compounds containing six-membered rings having three nitrogen atoms as the only ring hetero atoms, not provided for by group C07D251/00
- C07D253/08—Heterocyclic compounds containing six-membered rings having three nitrogen atoms as the only ring hetero atoms, not provided for by group C07D251/00 condensed with carbocyclic rings or ring systems
- C07D253/10—Condensed 1,2,4-triazines; Hydrogenated condensed 1,2,4-triazines
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2538179A DE2538179C2 (de) | 1975-08-27 | 1975-08-27 | 3-Alkoxy-benzo-1,2,4-triazine, Verfahren zu ihrer Herstellung sowie ihre Verwendung als Fungizide |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1060017A true CA1060017A (en) | 1979-08-07 |
Family
ID=5954983
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA259,907A Expired CA1060017A (en) | 1975-08-27 | 1976-08-26 | 3-alkoxy-benzo-1,2,4-triazines, process for their preparation and their use as fungicides and bactericides |
Country Status (27)
| Country | Link |
|---|---|
| US (1) | US4067981A (en, 2012) |
| JP (1) | JPS5231085A (en, 2012) |
| AR (1) | AR217063A1 (en, 2012) |
| AT (1) | AT348293B (en, 2012) |
| AU (1) | AU498333B2 (en, 2012) |
| BE (1) | BE845529A (en, 2012) |
| BR (1) | BR7605641A (en, 2012) |
| CA (1) | CA1060017A (en, 2012) |
| CH (1) | CH618974A5 (en, 2012) |
| CS (1) | CS189028B2 (en, 2012) |
| DD (1) | DD127563A5 (en, 2012) |
| DE (1) | DE2538179C2 (en, 2012) |
| DK (1) | DK150614B (en, 2012) |
| FR (1) | FR2322140A1 (en, 2012) |
| GB (1) | GB1494818A (en, 2012) |
| HU (1) | HU178986B (en, 2012) |
| IE (1) | IE43662B1 (en, 2012) |
| IL (1) | IL50343A (en, 2012) |
| IT (1) | IT1064914B (en, 2012) |
| LU (1) | LU75665A1 (en, 2012) |
| NL (1) | NL7609509A (en, 2012) |
| PL (1) | PL99306B1 (en, 2012) |
| RO (1) | RO70191A (en, 2012) |
| SE (1) | SE424323B (en, 2012) |
| SU (1) | SU637066A3 (en, 2012) |
| TR (1) | TR18900A (en, 2012) |
| ZA (1) | ZA765132B (en, 2012) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2740887A1 (de) * | 1977-09-10 | 1979-03-22 | Bayer Ag | Mittel zur bekaempfung von pflanzenbakteriosen |
| DE2910974A1 (de) * | 1979-03-21 | 1981-02-19 | Bayer Ag | 3-sulfonyl-benzo-1,2,4-triazine und -benzo-1,2,4-triazin-1-oxide, verfahren zu ihrer herstellung sowie ihre verwendung als antimikrobielle mittel |
| US4497950A (en) * | 1983-01-31 | 1985-02-05 | Polaroid Corporation | Benzotriazine compounds |
| US4420551A (en) * | 1983-01-31 | 1983-12-13 | Polaroid Corporation | Novel benzotriazine developers and photographic product and method |
| US5175287A (en) * | 1986-09-25 | 1992-12-29 | S R I International | Process for preparing 1,2,4-benzotriazine oxides |
| DE3790581T1 (en, 2012) * | 1986-09-25 | 1988-08-25 | ||
| US5624925A (en) | 1986-09-25 | 1997-04-29 | Sri International | 1,2,4-benzotriazine oxides as radiosensitizers and selective cytotoxic agents |
| JPH0612048Y2 (ja) * | 1987-06-19 | 1994-03-30 | 日立金属株式会社 | アンカ−ボルトの据付装置 |
| IE62911B1 (en) * | 1988-03-18 | 1995-03-08 | Stanford Res Inst Int | 1,2,4-benzotriazine oxides as radiosensitizers and selective cytotoxic agents |
| GR1000941B (el) * | 1989-03-17 | 1993-03-16 | Stanford Res Inst Int | Μεθοδος παρασκευης οξειδιων 1,2,4,βενζοτριαζινης. |
| DE4244009A1 (de) * | 1992-12-24 | 1994-06-30 | Boehringer Mannheim Gmbh | Verwendung von Benzotriazinen als PLA¶2¶-Inhibitoren, neue Benzotriazine, Verfahren zu ihrer Herstellung und Arzneimittel |
| CO5210943A1 (es) * | 1999-05-04 | 2002-10-30 | Novartis Ag | Compuestos plaguicidas derivados de triazina, composiciones para el control de plagas que comprenden dicho compuesto y cuando menos un auxiliar y metodos para controlar plagas |
| DE10237264A1 (de) * | 2002-08-14 | 2004-03-04 | Schülke & Mayr GmbH | Wässrige Dispersion mit fungizider und algizider Wirkung |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DD83869A (en, 2012) * | ||||
| US2489354A (en) * | 1947-01-10 | 1949-11-29 | Merck & Co Inc | Benzotriazines |
| US2489357A (en) * | 1947-01-10 | 1949-11-29 | Merck & Co Inc | Benzotriazines |
| CH487171A (de) * | 1963-10-22 | 1970-03-15 | Siegfried Ag | Verfahren zur Herstellung therapeutisch wirksamer 1,2-Dihydro-1,2,4-benztriazine |
| CH514610A (de) * | 1967-09-27 | 1971-10-31 | Siegfried Ag | Verfahren zur Herstellung von fluorsubstituierten 1,2,4-Benztriazin-Derivaten |
| IE38778B1 (en) * | 1973-02-02 | 1978-05-24 | Ciba Geigy | New 1,2,4-benzotriazine derivatives |
-
1975
- 1975-08-27 DE DE2538179A patent/DE2538179C2/de not_active Expired
-
1976
- 1976-08-23 CH CH1067976A patent/CH618974A5/de not_active IP Right Cessation
- 1976-08-24 IL IL7650343A patent/IL50343A/xx unknown
- 1976-08-25 SU SU762389902A patent/SU637066A3/ru active
- 1976-08-25 IT IT26544/76A patent/IT1064914B/it active
- 1976-08-25 CS CS765520A patent/CS189028B2/cs unknown
- 1976-08-25 RO RO7687362A patent/RO70191A/ro unknown
- 1976-08-25 TR TR18900A patent/TR18900A/xx unknown
- 1976-08-25 GB GB35342/76A patent/GB1494818A/en not_active Expired
- 1976-08-25 DD DD194462A patent/DD127563A5/xx unknown
- 1976-08-26 US US05/717,969 patent/US4067981A/en not_active Expired - Lifetime
- 1976-08-26 BR BR7605641A patent/BR7605641A/pt unknown
- 1976-08-26 SE SE7609460A patent/SE424323B/xx not_active IP Right Cessation
- 1976-08-26 IE IE1905/76A patent/IE43662B1/en unknown
- 1976-08-26 CA CA259,907A patent/CA1060017A/en not_active Expired
- 1976-08-26 DK DK387376AA patent/DK150614B/da not_active Application Discontinuation
- 1976-08-26 NL NL7609509A patent/NL7609509A/xx not_active Application Discontinuation
- 1976-08-26 LU LU75665A patent/LU75665A1/xx unknown
- 1976-08-26 PL PL1976192021A patent/PL99306B1/pl unknown
- 1976-08-26 BE BE170084A patent/BE845529A/xx not_active IP Right Cessation
- 1976-08-26 ZA ZA765132A patent/ZA765132B/xx unknown
- 1976-08-27 AR AR264498A patent/AR217063A1/es active
- 1976-08-27 JP JP51101767A patent/JPS5231085A/ja active Pending
- 1976-08-27 HU HU76BA3444A patent/HU178986B/hu unknown
- 1976-08-27 AT AT637976A patent/AT348293B/de not_active IP Right Cessation
- 1976-08-27 AU AU17212/76A patent/AU498333B2/en not_active Expired
- 1976-08-27 FR FR7625900A patent/FR2322140A1/fr active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| IE43662B1 (en) | 1981-04-22 |
| PL99306B1 (pl) | 1978-07-31 |
| US4067981A (en) | 1978-01-10 |
| AU498333B2 (en) | 1979-03-01 |
| AT348293B (de) | 1979-02-12 |
| AR217063A1 (es) | 1980-02-29 |
| DD127563A5 (en, 2012) | 1977-10-05 |
| AU1721276A (en) | 1978-03-02 |
| DE2538179A1 (de) | 1977-03-10 |
| SU637066A3 (ru) | 1978-12-05 |
| TR18900A (tr) | 1977-11-10 |
| IL50343A0 (en) | 1976-10-31 |
| JPS5231085A (en) | 1977-03-09 |
| FR2322140B1 (en, 2012) | 1981-03-06 |
| LU75665A1 (en, 2012) | 1977-04-27 |
| DE2538179C2 (de) | 1986-05-28 |
| GB1494818A (en) | 1977-12-14 |
| BR7605641A (pt) | 1977-08-09 |
| DK150614B (da) | 1987-04-21 |
| IL50343A (en) | 1979-11-30 |
| HU178986B (en) | 1982-07-28 |
| DK387376A (da) | 1977-02-28 |
| IT1064914B (it) | 1985-02-25 |
| NL7609509A (nl) | 1977-03-01 |
| SE7609460L (sv) | 1977-02-28 |
| CH618974A5 (en, 2012) | 1980-08-29 |
| ATA637976A (de) | 1978-06-15 |
| RO70191A (ro) | 1982-09-09 |
| CS189028B2 (en) | 1979-03-30 |
| ZA765132B (en) | 1977-07-27 |
| FR2322140A1 (fr) | 1977-03-25 |
| SE424323B (sv) | 1982-07-12 |
| IE43662L (en) | 1977-02-27 |
| BE845529A (fr) | 1977-02-28 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CA1212952A (en) | 1-phenyl-2-triazolyl-ethyl ether derivatives and their use as fungicides | |
| CA1060017A (en) | 3-alkoxy-benzo-1,2,4-triazines, process for their preparation and their use as fungicides and bactericides | |
| US3940415A (en) | 1-(Imidazolyl-1)-2-aryloxy-3-hydroxy-alkanes | |
| CA1106386A (en) | Metal salt complexes of 1-phenyl-2-triazolyl-ethyl derivatives and their use as fungicides | |
| EP0213718B1 (en) | 1-dimethylcarbamoyl-3-substituted-5-substituted-1h-1,2,4-triazoles | |
| EP0047405B1 (de) | Azolylalkyl-Derivate, Verfahren zu ihrer Herstellung und ihre Verwendung als Fungizide | |
| EP0130366A2 (de) | Arylalkylimidazolium- und -triazoliumsalze, Verfahren zu ihrer Herstellung und ihre Verwendung als Mikrozide | |
| US4098894A (en) | Triphenyl-1,2,3-triazolyl-(1)-methanes, and compositions and methods for combating fungi and bacteria employing them | |
| GB1580389A (en) | azolyl ketones and their use as fungicides | |
| US3972891A (en) | 1-Phenoxy-1-[halo-1,2,4-triazolyl-(1)]-3,3-dimethyl-butan-2-ones | |
| US4134988A (en) | 2-acyloxy-1-phenoxy-1-imidazolyl-(1)-3,3-dimethyl-butanes | |
| CS202516B2 (en) | Fungicide means and method of making the active substances | |
| EP0193065B1 (de) | Morpholinderivate, Verfahren zu ihrer Herstellung und ihre Verwendung als Fungizide | |
| US4349556A (en) | Pesticidally active 1-acyloxy-1-phenyl-2-azolyl-ethanes | |
| EP0023307A1 (de) | N-(Alpha-Chlorpropionyl)-1,2,3,4-tetrahydro-iso-chinolin, Verfahren zu dessen Herstellung und dessen Verwendung als Gegenmittel zum Schutz von Kulturpflanzen vor Schädigungen durch Herbizide | |
| DE3103069A1 (de) | Dibenzofuranderivate, verfahren zu ihrer herstellung und ihre verwendung als fungizide | |
| DE3321023A1 (de) | Triazolylalkohole, verfahren zu ihrer herstellung und ihre verwendung als fungizide | |
| EP0023305A1 (de) | Verwendung von N,N'-Bis-(halogenacyl)-diaza-cycloalkanen zum Schutz von Kulturpflanzen vor Schädigungen durch Herbizide | |
| US4073901A (en) | Metal complexes of N-trityl-azoles for combatting fungi | |
| EP0023306A1 (de) | N-(Alpha-Chlorpropionyl)-1,2,3,4-tetrahydro-chinaldin, Verfahren zu dessen Herstellung und dessen Verwendung als Gegenmittel zum Schutz von Kulturpflanzen vor Schädigungen durch Herbizide | |
| US3769411A (en) | Fungicidal 1,2,4-4h-triazole derivatives | |
| US4053620A (en) | Combating fungi with 1-aryl-5-alkylidene-2,4-dioxo-imidazolidines | |
| US4034104A (en) | Carbamic acid esters of gallic acid, their esters, and heavy metal salts | |
| DE2828303A1 (de) | Verwendung von n,n-diallyl-dichloracetamid zur verbesserung der kulturpflanzen- vertraeglichkeit von herbizid wirksamen acetaniliden | |
| EP0244641B1 (de) | 1,4-Cyclohexandiamine, Verfahren zu ihrer Herstellung und ihre Verwendung als Fungizide |