GB1601423A - Optionally substituted 1- or 4-aralkyl-1,2,4-triazoles and their use as fungicides - Google Patents
Optionally substituted 1- or 4-aralkyl-1,2,4-triazoles and their use as fungicides Download PDFInfo
- Publication number
- GB1601423A GB1601423A GB19466/78A GB1946678A GB1601423A GB 1601423 A GB1601423 A GB 1601423A GB 19466/78 A GB19466/78 A GB 19466/78A GB 1946678 A GB1946678 A GB 1946678A GB 1601423 A GB1601423 A GB 1601423A
- Authority
- GB
- United Kingdom
- Prior art keywords
- compound
- optionally substituted
- metal salt
- cyano
- triazolyl
- 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
- 239000000417 fungicide Substances 0.000 title abstract description 16
- -1 aralkyl radical Chemical class 0.000 claims abstract description 89
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 36
- 125000003118 aryl group Chemical group 0.000 claims abstract description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 12
- 239000001257 hydrogen Substances 0.000 claims abstract description 11
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 4
- 150000003839 salts Chemical class 0.000 claims description 81
- 150000001875 compounds Chemical class 0.000 claims description 79
- 229910052751 metal Inorganic materials 0.000 claims description 45
- 239000002184 metal Substances 0.000 claims description 45
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 32
- 239000002253 acid Substances 0.000 claims description 29
- 125000001376 1,2,4-triazolyl group Chemical group N1N=C(N=C1)* 0.000 claims description 25
- 125000001424 substituent group Chemical group 0.000 claims description 24
- 229910052736 halogen Inorganic materials 0.000 claims description 21
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 20
- 150000002367 halogens Chemical class 0.000 claims description 20
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 20
- 238000000034 method Methods 0.000 claims description 18
- 239000000203 mixture Substances 0.000 claims description 18
- 238000002360 preparation method Methods 0.000 claims description 17
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 12
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- 125000001624 naphthyl group Chemical group 0.000 claims description 10
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 9
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims description 8
- 229910052799 carbon Inorganic materials 0.000 claims description 8
- 125000003107 substituted aryl group Chemical group 0.000 claims description 8
- 125000004768 (C1-C4) alkylsulfinyl group Chemical group 0.000 claims description 7
- 125000004414 alkyl thio group Chemical group 0.000 claims description 7
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 7
- 125000004953 trihalomethyl group Chemical group 0.000 claims description 7
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims description 6
- 239000004480 active ingredient Substances 0.000 claims description 6
- 125000000041 C6-C10 aryl group Chemical group 0.000 claims description 5
- 150000001450 anions Chemical group 0.000 claims description 5
- 150000001768 cations Chemical class 0.000 claims description 5
- 125000002993 cycloalkylene group Chemical group 0.000 claims description 5
- 230000000855 fungicidal effect Effects 0.000 claims description 5
- 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 claims description 4
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 4
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims description 4
- 241000233866 Fungi Species 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
- 239000003085 diluting agent Substances 0.000 claims description 3
- 150000002431 hydrogen Chemical class 0.000 claims description 3
- 230000000737 periodic effect Effects 0.000 claims description 3
- 230000003032 phytopathogenic effect Effects 0.000 claims description 3
- 239000004094 surface-active agent Substances 0.000 claims description 3
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 2
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 2
- 125000000081 (C5-C8) cycloalkenyl group Chemical group 0.000 claims description 2
- 125000004649 C2-C8 alkynyl group Chemical group 0.000 claims description 2
- 230000009418 agronomic effect Effects 0.000 claims description 2
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims description 2
- 125000004104 aryloxy group Chemical group 0.000 claims description 2
- 239000012141 concentrate Substances 0.000 claims description 2
- 239000004495 emulsifiable concentrate Substances 0.000 claims description 2
- 239000000839 emulsion Substances 0.000 claims description 2
- 230000009969 flowable effect Effects 0.000 claims description 2
- 239000008187 granular material Substances 0.000 claims description 2
- 238000007429 general method Methods 0.000 claims 2
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 1
- 239000000428 dust Substances 0.000 claims 1
- 239000004563 wettable powder Substances 0.000 claims 1
- 241000196324 Embryophyta Species 0.000 abstract description 10
- 150000000178 1,2,4-triazoles Chemical class 0.000 abstract description 5
- 125000000392 cycloalkenyl group Chemical group 0.000 abstract description 3
- 239000000126 substance Substances 0.000 abstract description 2
- 230000009885 systemic effect Effects 0.000 abstract description 2
- 125000003342 alkenyl group Chemical group 0.000 abstract 1
- 125000000304 alkynyl group Chemical group 0.000 abstract 1
- 150000005840 aryl radicals Chemical class 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- 150000003254 radicals Chemical class 0.000 abstract 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 24
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- 239000002904 solvent Substances 0.000 description 17
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 16
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 12
- 239000000243 solution Substances 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 description 10
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 10
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 8
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 8
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 8
- 229910017604 nitric acid Inorganic materials 0.000 description 8
- 239000002244 precipitate Substances 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 8
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 6
- 235000019341 magnesium sulphate Nutrition 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- SNTWKPAKVQFCCF-UHFFFAOYSA-N 2,3-dihydro-1h-triazole Chemical compound N1NC=CN1 SNTWKPAKVQFCCF-UHFFFAOYSA-N 0.000 description 5
- 239000012259 ether extract Substances 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 5
- FMGOPNNYXMJSQP-UHFFFAOYSA-N 2-(2,4-dichlorophenyl)hexyl methanesulfonate Chemical compound CCCCC(COS(C)(=O)=O)C1=CC=C(Cl)C=C1Cl FMGOPNNYXMJSQP-UHFFFAOYSA-N 0.000 description 4
- BSIWCGSVYGGXGB-UHFFFAOYSA-N 4-[2-(2,4-dichlorophenyl)hexyl]-1,2,4-triazole Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(CCCC)CN1C=NN=C1 BSIWCGSVYGGXGB-UHFFFAOYSA-N 0.000 description 4
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- 239000012458 free base Substances 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 239000011592 zinc chloride Substances 0.000 description 4
- 235000005074 zinc chloride Nutrition 0.000 description 4
- NEDKLHZEQYTKIX-UHFFFAOYSA-N 1-[2-(2,4-dichlorophenyl)hexyl]-1,2,4-triazole Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(CCCC)CN1C=NC=N1 NEDKLHZEQYTKIX-UHFFFAOYSA-N 0.000 description 3
- UJNHMACIAJGTAF-UHFFFAOYSA-N 2-(bromomethyl)-2-(2,4-dichlorophenyl)hexanenitrile Chemical compound CCCCC(CBr)(C#N)C1=CC=C(Cl)C=C1Cl UJNHMACIAJGTAF-UHFFFAOYSA-N 0.000 description 3
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 240000005979 Hordeum vulgare Species 0.000 description 3
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 240000007594 Oryza sativa Species 0.000 description 3
- 244000046052 Phaseolus vulgaris Species 0.000 description 3
- 240000003768 Solanum lycopersicum Species 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 241000209140 Triticum Species 0.000 description 3
- 240000006677 Vicia faba Species 0.000 description 3
- 235000009754 Vitis X bourquina Nutrition 0.000 description 3
- 235000012333 Vitis X labruscana Nutrition 0.000 description 3
- 240000006365 Vitis vinifera Species 0.000 description 3
- 235000014787 Vitis vinifera Nutrition 0.000 description 3
- 239000002671 adjuvant Substances 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 3
- 239000002274 desiccant Substances 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 238000011065 in-situ storage Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 229910052725 zinc Inorganic materials 0.000 description 3
- 239000011701 zinc Substances 0.000 description 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 2
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 description 2
- 125000006705 (C5-C7) cycloalkyl group Chemical group 0.000 description 2
- XIRJSRFRCSFOHV-UHFFFAOYSA-O 1-[2-(2,4-dichlorophenyl)hexyl]-1h-1,2,4-triazol-1-ium;nitrate Chemical compound [O-][N+]([O-])=O.C=1C=C(Cl)C=C(Cl)C=1C(CCCC)C[NH+]1C=NC=N1 XIRJSRFRCSFOHV-UHFFFAOYSA-O 0.000 description 2
- ZCVNZKGHIZQXHV-UHFFFAOYSA-N 2-(2,4-dichlorophenyl)-2-(1,2,4-triazol-4-ylmethyl)hexanenitrile Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(CCCC)(C#N)CN1C=NN=C1 ZCVNZKGHIZQXHV-UHFFFAOYSA-N 0.000 description 2
- DPIIDIOPYDOXJT-UHFFFAOYSA-N 2-(2,4-dichlorophenyl)hexan-1-amine Chemical compound CCCCC(CN)C1=CC=C(Cl)C=C1Cl DPIIDIOPYDOXJT-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- 125000004399 C1-C4 alkenyl group Chemical group 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 2
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 235000007688 Lycopersicon esculentum Nutrition 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 241000233626 Plasmopara Species 0.000 description 2
- 241000520648 Pyrenophora teres Species 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 235000021307 Triticum Nutrition 0.000 description 2
- 235000010749 Vicia faba Nutrition 0.000 description 2
- FPIPGXGPPPQFEQ-OVSJKPMPSA-N all-trans-retinol Chemical compound OC\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-OVSJKPMPSA-N 0.000 description 2
- 239000000908 ammonium hydroxide Substances 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- HTZCNXWZYVXIMZ-UHFFFAOYSA-M benzyl(triethyl)azanium;chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC1=CC=CC=C1 HTZCNXWZYVXIMZ-UHFFFAOYSA-M 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 239000012990 dithiocarbamate Substances 0.000 description 2
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- WHDGWKAJBYRJJL-UHFFFAOYSA-K ferbam Chemical compound [Fe+3].CN(C)C([S-])=S.CN(C)C([S-])=S.CN(C)C([S-])=S WHDGWKAJBYRJJL-UHFFFAOYSA-K 0.000 description 2
- 239000012280 lithium aluminium hydride Substances 0.000 description 2
- YKSNLCVSTHTHJA-UHFFFAOYSA-L maneb Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S YKSNLCVSTHTHJA-UHFFFAOYSA-L 0.000 description 2
- 229910052759 nickel Inorganic materials 0.000 description 2
- 150000002823 nitrates Chemical class 0.000 description 2
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 2
- NVMNEWNGLGACBB-UHFFFAOYSA-N sodium;1,2-diaza-4-azanidacyclopenta-2,5-diene Chemical compound [Na+].C=1N=C[N-]N=1 NVMNEWNGLGACBB-UHFFFAOYSA-N 0.000 description 2
- 239000002689 soil Substances 0.000 description 2
- 238000005507 spraying Methods 0.000 description 2
- 238000010561 standard procedure Methods 0.000 description 2
- HWCKGOZZJDHMNC-UHFFFAOYSA-M tetraethylammonium bromide Chemical compound [Br-].CC[N+](CC)(CC)CC HWCKGOZZJDHMNC-UHFFFAOYSA-M 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- 150000003852 triazoles Chemical class 0.000 description 2
- 125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- DUBNHZYBDBBJHD-UHFFFAOYSA-L ziram Chemical compound [Zn+2].CN(C)C([S-])=S.CN(C)C([S-])=S DUBNHZYBDBBJHD-UHFFFAOYSA-L 0.000 description 2
- AOSZTAHDEDLTLQ-AZKQZHLXSA-N (1S,2S,4R,8S,9S,11S,12R,13S,19S)-6-[(3-chlorophenyl)methyl]-12,19-difluoro-11-hydroxy-8-(2-hydroxyacetyl)-9,13-dimethyl-6-azapentacyclo[10.8.0.02,9.04,8.013,18]icosa-14,17-dien-16-one Chemical compound C([C@@H]1C[C@H]2[C@H]3[C@]([C@]4(C=CC(=O)C=C4[C@@H](F)C3)C)(F)[C@@H](O)C[C@@]2([C@@]1(C1)C(=O)CO)C)N1CC1=CC=CC(Cl)=C1 AOSZTAHDEDLTLQ-AZKQZHLXSA-N 0.000 description 1
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 description 1
- 125000001399 1,2,3-triazolyl group Chemical group N1N=NC(=C1)* 0.000 description 1
- JCIIKRHCWVHVFF-UHFFFAOYSA-N 1,2,4-thiadiazol-5-amine;hydrochloride Chemical compound Cl.NC1=NC=NS1 JCIIKRHCWVHVFF-UHFFFAOYSA-N 0.000 description 1
- MPPPKRYCTPRNTB-UHFFFAOYSA-N 1-bromobutane Chemical compound CCCCBr MPPPKRYCTPRNTB-UHFFFAOYSA-N 0.000 description 1
- WPWHSFAFEBZWBB-UHFFFAOYSA-N 1-butyl radical Chemical group [CH2]CCC WPWHSFAFEBZWBB-UHFFFAOYSA-N 0.000 description 1
- GRUHREVRSOOQJG-UHFFFAOYSA-N 2,4-dichlorobenzonitrile Chemical compound ClC1=CC=C(C#N)C(Cl)=C1 GRUHREVRSOOQJG-UHFFFAOYSA-N 0.000 description 1
- 125000001917 2,4-dinitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C(=C1*)[N+]([O-])=O)[N+]([O-])=O 0.000 description 1
- OMALVIISEIXNAU-UHFFFAOYSA-N 2-(2,4-dichlorophenyl)-2-(1,2,4-triazol-1-ylmethyl)hexanenitrile Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(CCCC)(C#N)CN1C=NC=N1 OMALVIISEIXNAU-UHFFFAOYSA-N 0.000 description 1
- JHEHAMUCLHEDQJ-UHFFFAOYSA-O 2-(2,4-dichlorophenyl)-2-(1h-1,2,4-triazol-1-ium-1-ylmethyl)hexanenitrile;nitrate Chemical compound [O-][N+]([O-])=O.C=1C=C(Cl)C=C(Cl)C=1C(CCCC)(C#N)C[NH+]1C=NC=N1 JHEHAMUCLHEDQJ-UHFFFAOYSA-O 0.000 description 1
- GXTMDKIKOLGAON-UHFFFAOYSA-N 2-(2,4-dichlorophenyl)hexan-1-ol Chemical compound CCCCC(CO)C1=CC=C(Cl)C=C1Cl GXTMDKIKOLGAON-UHFFFAOYSA-N 0.000 description 1
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- 125000004211 3,5-difluorophenyl group Chemical group [H]C1=C(F)C([H])=C(*)C([H])=C1F 0.000 description 1
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- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- 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
- A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
- A01N43/647—Triazoles; Hydrogenated triazoles
- A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Dentistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Plant Pathology (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US79871677A | 1977-05-19 | 1977-05-19 | |
| US79828677A | 1977-05-19 | 1977-05-19 | |
| KR1019780002635A KR830000082B1 (ko) | 1977-05-19 | 1978-08-31 | 1-아랄킬-1,2,4-트리아졸의 제조방법 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1601423A true GB1601423A (en) | 1981-10-28 |
Family
ID=27348165
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB19466/78A Expired GB1601423A (en) | 1977-05-19 | 1978-05-15 | Optionally substituted 1- or 4-aralkyl-1,2,4-triazoles and their use as fungicides |
Country Status (7)
| Country | Link |
|---|---|
| JP (1) | JPS5416474A (enrdf_load_stackoverflow) |
| CA (1) | CA1117537A (enrdf_load_stackoverflow) |
| CH (1) | CH633281A5 (enrdf_load_stackoverflow) |
| DE (1) | DE2821971C2 (enrdf_load_stackoverflow) |
| FR (1) | FR2391200A1 (enrdf_load_stackoverflow) |
| GB (1) | GB1601423A (enrdf_load_stackoverflow) |
| NL (2) | NL189408C (enrdf_load_stackoverflow) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0354689A1 (en) * | 1988-08-04 | 1990-02-14 | Imperial Chemical Industries Plc | Diphenylethane derivatives |
| US4999364A (en) * | 1988-08-08 | 1991-03-12 | Imperial Chemical Industries Plc | Azole derivatives |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4366165A (en) * | 1977-05-19 | 1982-12-28 | Rohm And Haas Company | 1 and 4-Arylcyanoalkyl-1,2,4-triazoles and fungicidal use |
| JPS5892667A (ja) * | 1981-11-27 | 1983-06-02 | ロ−ム・アンド・ハ−ス・コンパニ− | 除草作用のあるフエニルアセトニトリル類 |
| DE3329213A1 (de) * | 1983-08-10 | 1985-02-21 | Schering AG, 1000 Berlin und 4709 Bergkamen | Azolyl-propannitrile, verfahren zur herstellung dieser verbindungen sowie diese enthaltende biozide mittel |
| CA1227801A (en) * | 1983-11-10 | 1987-10-06 | Ted T. Fujimoto | .alpha.-ALKYL-.alpha.-(4-HALOPHENYL)-1H-1,2,4-TRIAZOLE-1- PROPANENITRILES |
| FR2655514A1 (fr) * | 1989-12-13 | 1991-06-14 | Rhone Poulenc Agrochimie | Association fongicide a effet synergique a base d'une morpholine et d'un triazole. |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4085209A (en) * | 1975-02-05 | 1978-04-18 | Rohm And Haas Company | Preparation and safening effect of 1-substituted imidazole metal salt complexes |
-
1978
- 1978-04-24 NL NLAANVRAGE7804341,A patent/NL189408C/xx not_active IP Right Cessation
- 1978-05-08 CA CA000302797A patent/CA1117537A/en not_active Expired
- 1978-05-15 GB GB19466/78A patent/GB1601423A/en not_active Expired
- 1978-05-17 CH CH534078A patent/CH633281A5/fr not_active IP Right Cessation
- 1978-05-18 FR FR7814776A patent/FR2391200A1/fr active Granted
- 1978-05-19 DE DE2821971A patent/DE2821971C2/de not_active Expired - Lifetime
- 1978-05-19 JP JP5986178A patent/JPS5416474A/ja active Granted
-
1997
- 1997-07-10 NL NL971010C patent/NL971010I2/nl unknown
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0354689A1 (en) * | 1988-08-04 | 1990-02-14 | Imperial Chemical Industries Plc | Diphenylethane derivatives |
| US5006543A (en) * | 1988-08-04 | 1991-04-09 | Imperial Chemical Industries Plc | Diphenylethane derivatives |
| US4999364A (en) * | 1988-08-08 | 1991-03-12 | Imperial Chemical Industries Plc | Azole derivatives |
Also Published As
| Publication number | Publication date |
|---|---|
| DE2821971C2 (de) | 1994-01-27 |
| NL971010I2 (nl) | 1998-01-05 |
| DE2821971A1 (de) | 1978-11-30 |
| FR2391200B1 (enrdf_load_stackoverflow) | 1980-07-18 |
| JPS5416474A (en) | 1979-02-07 |
| NL189408C (nl) | 1993-04-01 |
| NL971010I1 (nl) | 1997-09-01 |
| FR2391200A1 (fr) | 1978-12-15 |
| CH633281A5 (en) | 1982-11-30 |
| NL7804341A (nl) | 1978-11-21 |
| JPH0152390B2 (enrdf_load_stackoverflow) | 1989-11-08 |
| NL189408B (nl) | 1992-11-02 |
| CA1117537A (en) | 1982-02-02 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| 48S | Specification amended (sect. 8/1949) | ||
| SPA | Amended specification published | ||
| 704A | Declaration that licence is not available as of right for an excepted use (par. 4a/1977) | ||
| CTFF | Supplementary protection certificate filed |
Free format text: SPC/GB97/026, 970715 |
|
| PE20 | Patent expired after termination of 20 years |
Effective date: 19980514 |
|
| CTFG | Supplementary protection certificate granted |
Free format text: SPC/GB97/026, 980528, EXPIRES: 20030514 |
|
| CTFE | Supplementary protection certificate entered into force |
Free format text: SPC/GB97/026, 19980515, EXPIRES: 20030514 |
|
| SPCE | Supplementary protection certificate expired |
Free format text: SPC/GB97/124, 20001124 |