KR20120112423A - 복소환식 이환 치환된 아졸릴 벤젠 살진균제 - Google Patents
복소환식 이환 치환된 아졸릴 벤젠 살진균제 Download PDFInfo
- Publication number
- KR20120112423A KR20120112423A KR1020127013672A KR20127013672A KR20120112423A KR 20120112423 A KR20120112423 A KR 20120112423A KR 1020127013672 A KR1020127013672 A KR 1020127013672A KR 20127013672 A KR20127013672 A KR 20127013672A KR 20120112423 A KR20120112423 A KR 20120112423A
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- KR
- South Korea
- Prior art keywords
- methyl
- alkyl
- compound
- ring
- haloalkyl
- 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.)
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- 125000000623 heterocyclic group Chemical group 0.000 title claims abstract description 48
- 239000000417 fungicide Substances 0.000 title claims description 262
- IRTLROCMFSDSNF-UHFFFAOYSA-N 2-phenyl-1h-pyrrole Chemical class C1=CNC(C=2C=CC=CC=2)=C1 IRTLROCMFSDSNF-UHFFFAOYSA-N 0.000 title description 4
- 150000001875 compounds Chemical class 0.000 claims abstract description 317
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 82
- 238000000034 method Methods 0.000 claims abstract description 66
- 201000010099 disease Diseases 0.000 claims abstract description 39
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 39
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 37
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 34
- 125000001424 substituent group Chemical group 0.000 claims abstract description 34
- 125000004429 atom Chemical group 0.000 claims abstract description 33
- 150000003839 salts Chemical class 0.000 claims abstract description 28
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 23
- 125000004434 sulfur atom Chemical group 0.000 claims abstract description 15
- 125000004430 oxygen atom Chemical group O* 0.000 claims abstract description 14
- 125000005842 heteroatom Chemical group 0.000 claims abstract description 7
- -1 C 1 -C 3 haloalkyl Chemical group 0.000 claims description 156
- 230000000855 fungicidal effect Effects 0.000 claims description 122
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 119
- 125000000217 alkyl group Chemical group 0.000 claims description 62
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims description 60
- 229910052736 halogen Inorganic materials 0.000 claims description 54
- 150000002367 halogens Chemical class 0.000 claims description 50
- 229910052739 hydrogen Inorganic materials 0.000 claims description 40
- 239000007787 solid Substances 0.000 claims description 39
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims description 31
- 239000007788 liquid Substances 0.000 claims description 29
- 239000003085 diluting agent Substances 0.000 claims description 27
- 125000001188 haloalkyl group Chemical group 0.000 claims description 25
- 125000003545 alkoxy group Chemical group 0.000 claims description 24
- 125000006645 (C3-C4) cycloalkyl group Chemical group 0.000 claims description 23
- 239000004094 surface-active agent Substances 0.000 claims description 22
- 125000006677 (C1-C3) haloalkoxy group Chemical group 0.000 claims description 17
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 17
- 229910052801 chlorine Inorganic materials 0.000 claims description 17
- 229910052731 fluorine Inorganic materials 0.000 claims description 16
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims description 15
- 229910052794 bromium Inorganic materials 0.000 claims description 15
- 125000003118 aryl group Chemical group 0.000 claims description 13
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 12
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 12
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 10
- 125000006660 (C3-C4) halocycloalkyl group Chemical group 0.000 claims description 9
- 125000003282 alkyl amino group Chemical group 0.000 claims description 9
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 8
- 244000000004 fungal plant pathogen Species 0.000 claims description 8
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 8
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims description 7
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 7
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 7
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 7
- 125000004473 dialkylaminocarbonyl group Chemical group 0.000 claims description 7
- 229910052717 sulfur Inorganic materials 0.000 claims description 7
- 125000004665 trialkylsilyl group Chemical group 0.000 claims description 7
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 6
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 6
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims description 6
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 6
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 6
- 125000005203 haloalkylcarbonyloxy group Chemical group 0.000 claims description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 5
- 125000005133 alkynyloxy group Chemical group 0.000 claims description 5
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 5
- 125000004992 haloalkylamino group Chemical group 0.000 claims description 5
- 125000005112 cycloalkylalkoxy group Chemical group 0.000 claims description 4
- 125000005201 cycloalkylcarbonyloxy group Chemical group 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 125000004768 (C1-C4) alkylsulfinyl group Chemical group 0.000 claims description 3
- 125000004771 (C1-C4) haloalkylsulfinyl group Chemical group 0.000 claims description 3
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 3
- 125000006771 (C1-C6) haloalkylthio group Chemical group 0.000 claims description 3
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 3
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 3
- 125000005291 haloalkenyloxy group Chemical group 0.000 claims 2
- 125000005292 haloalkynyloxy group Chemical group 0.000 claims 2
- 125000005366 cycloalkylthio group Chemical group 0.000 claims 1
- 125000006769 halocycloalkoxy group Chemical group 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 239000000203 mixture Substances 0.000 abstract description 100
- 150000001204 N-oxides Chemical class 0.000 abstract description 17
- 244000053095 fungal pathogen Species 0.000 abstract description 2
- 230000009471 action Effects 0.000 description 69
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 54
- 241000196324 Embryophyta Species 0.000 description 48
- 238000006243 chemical reaction Methods 0.000 description 46
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 45
- 239000011541 reaction mixture Substances 0.000 description 41
- 230000015572 biosynthetic process Effects 0.000 description 40
- 239000002904 solvent Substances 0.000 description 39
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 32
- 238000003786 synthesis reaction Methods 0.000 description 31
- 238000009472 formulation Methods 0.000 description 28
- 241000233866 Fungi Species 0.000 description 27
- 230000012010 growth Effects 0.000 description 26
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 24
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 23
- 239000000460 chlorine Substances 0.000 description 23
- 239000000243 solution Substances 0.000 description 22
- 238000012360 testing method Methods 0.000 description 21
- 239000003112 inhibitor Substances 0.000 description 20
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 19
- 239000004480 active ingredient Substances 0.000 description 19
- 150000001721 carbon Chemical group 0.000 description 19
- 230000002538 fungal effect Effects 0.000 description 19
- 239000000126 substance Substances 0.000 description 19
- 239000000725 suspension Substances 0.000 description 19
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 18
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 18
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- 150000001412 amines Chemical class 0.000 description 18
- 229930182558 Sterol Natural products 0.000 description 17
- 235000003702 sterols Nutrition 0.000 description 17
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 16
- 150000003432 sterols Chemical class 0.000 description 16
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 14
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 14
- 125000004122 cyclic group Chemical group 0.000 description 14
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 14
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 14
- 239000011734 sodium Substances 0.000 description 14
- 244000052769 pathogen Species 0.000 description 13
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 12
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 239000012267 brine Substances 0.000 description 12
- 238000002360 preparation method Methods 0.000 description 12
- 229920006395 saturated elastomer Polymers 0.000 description 12
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 12
- 102000004190 Enzymes Human genes 0.000 description 11
- 108090000790 Enzymes Proteins 0.000 description 11
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 11
- 239000003054 catalyst Substances 0.000 description 11
- 230000005764 inhibitory process Effects 0.000 description 11
- 229910052757 nitrogen Inorganic materials 0.000 description 11
- 230000008569 process Effects 0.000 description 11
- 241000209140 Triticum Species 0.000 description 10
- 235000021307 Triticum Nutrition 0.000 description 10
- 239000002585 base Substances 0.000 description 10
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 10
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical group NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- GBRBMTNGQBKBQE-UHFFFAOYSA-L copper;diiodide Chemical compound I[Cu]I GBRBMTNGQBKBQE-UHFFFAOYSA-L 0.000 description 9
- 235000014113 dietary fatty acids Nutrition 0.000 description 9
- 239000003480 eluent Substances 0.000 description 9
- 239000000194 fatty acid Substances 0.000 description 9
- 229930195729 fatty acid Natural products 0.000 description 9
- 230000008099 melanin synthesis Effects 0.000 description 9
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 8
- 150000003857 carboxamides Chemical class 0.000 description 8
- 239000010949 copper Substances 0.000 description 8
- 229910052802 copper Inorganic materials 0.000 description 8
- 238000011161 development Methods 0.000 description 8
- 230000018109 developmental process Effects 0.000 description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 8
- 239000000543 intermediate Substances 0.000 description 8
- 239000003208 petroleum Substances 0.000 description 8
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 7
- GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 description 7
- LSBDFXRDZJMBSC-UHFFFAOYSA-N 2-phenylacetamide Chemical compound NC(=O)CC1=CC=CC=C1 LSBDFXRDZJMBSC-UHFFFAOYSA-N 0.000 description 7
- 101150065749 Churc1 gene Proteins 0.000 description 7
- 102100038239 Protein Churchill Human genes 0.000 description 7
- 238000004458 analytical method Methods 0.000 description 7
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 7
- 125000005843 halogen group Chemical group 0.000 description 7
- 125000001072 heteroaryl group Chemical group 0.000 description 7
- 238000004519 manufacturing process Methods 0.000 description 7
- 239000012528 membrane Substances 0.000 description 7
- 239000012299 nitrogen atmosphere Substances 0.000 description 7
- 230000001717 pathogenic effect Effects 0.000 description 7
- 150000003904 phospholipids Chemical class 0.000 description 7
- 229910000027 potassium carbonate Inorganic materials 0.000 description 7
- 125000001273 sulfonato group Chemical class [O-]S(*)(=O)=O 0.000 description 7
- 238000004809 thin layer chromatography Methods 0.000 description 7
- JRHPOFJADXHYBR-HTQZYQBOSA-N (1r,2r)-1-n,2-n-dimethylcyclohexane-1,2-diamine Chemical compound CN[C@@H]1CCCC[C@H]1NC JRHPOFJADXHYBR-HTQZYQBOSA-N 0.000 description 6
- WNZQDUSMALZDQF-UHFFFAOYSA-N 2-benzofuran-1(3H)-one Chemical compound C1=CC=C2C(=O)OCC2=C1 WNZQDUSMALZDQF-UHFFFAOYSA-N 0.000 description 6
- KANAQORHRUCTEH-UHFFFAOYSA-N 5-(3,4-dihydro-2h-chromen-6-yl)-1h-pyrazole Chemical compound C1=C2CCCOC2=CC=C1C=1C=CNN=1 KANAQORHRUCTEH-UHFFFAOYSA-N 0.000 description 6
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 6
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
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- 238000006069 Suzuki reaction reaction Methods 0.000 description 6
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- 150000002148 esters Chemical class 0.000 description 6
- 229910052740 iodine Inorganic materials 0.000 description 6
- AMSPWOYQQAWRRM-UHFFFAOYSA-N metrafenone Chemical compound COC1=CC=C(Br)C(C)=C1C(=O)C1=C(C)C=C(OC)C(OC)=C1OC AMSPWOYQQAWRRM-UHFFFAOYSA-N 0.000 description 6
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- YLZGKZDEFJIHIJ-UHFFFAOYSA-N (1-methylbenzimidazol-2-yl) carbamate Chemical compound C1=CC=C2N(C)C(OC(N)=O)=NC2=C1 YLZGKZDEFJIHIJ-UHFFFAOYSA-N 0.000 description 5
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- 150000001298 alcohols Chemical class 0.000 description 5
- 150000001408 amides Chemical class 0.000 description 5
- 230000003115 biocidal effect Effects 0.000 description 5
- DKVNPHBNOWQYFE-UHFFFAOYSA-N carbamodithioic acid Chemical compound NC(S)=S DKVNPHBNOWQYFE-UHFFFAOYSA-N 0.000 description 5
- 210000002421 cell wall Anatomy 0.000 description 5
- 238000006880 cross-coupling reaction Methods 0.000 description 5
- ACMXQHFNODYQAT-UHFFFAOYSA-N cyflufenamid Chemical compound FC1=CC=C(C(F)(F)F)C(C(NOCC2CC2)=NC(=O)CC=2C=CC=CC=2)=C1F ACMXQHFNODYQAT-UHFFFAOYSA-N 0.000 description 5
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
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- 239000005740 Boscalid Substances 0.000 description 4
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- DNVPQKQSNYMLRS-NXVQYWJNSA-N Ergosterol Natural products CC(C)[C@@H](C)C=C[C@H](C)[C@H]1CC[C@H]2C3=CC=C4C[C@@H](O)CC[C@]4(C)[C@@H]3CC[C@]12C DNVPQKQSNYMLRS-NXVQYWJNSA-N 0.000 description 4
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 4
- 101000615488 Homo sapiens Methyl-CpG-binding domain protein 2 Proteins 0.000 description 4
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 4
- 235000007688 Lycopersicon esculentum Nutrition 0.000 description 4
- XUMBMVFBXHLACL-UHFFFAOYSA-N Melanin Chemical compound O=C1C(=O)C(C2=CNC3=C(C(C(=O)C4=C32)=O)C)=C2C4=CNC2=C1C XUMBMVFBXHLACL-UHFFFAOYSA-N 0.000 description 4
- 239000005868 Metconazole Substances 0.000 description 4
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- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- WOSNCVAPUOFXEH-UHFFFAOYSA-N thifluzamide Chemical compound S1C(C)=NC(C(F)(F)F)=C1C(=O)NC1=C(Br)C=C(OC(F)(F)F)C=C1Br WOSNCVAPUOFXEH-UHFFFAOYSA-N 0.000 description 1
- BAKXBZPQTXCKRR-UHFFFAOYSA-N thiodicarb Chemical compound CSC(C)=NOC(=O)NSNC(=O)ON=C(C)SC BAKXBZPQTXCKRR-UHFFFAOYSA-N 0.000 description 1
- QGHREAKMXXNCOA-UHFFFAOYSA-N thiophanate-methyl Chemical compound COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC QGHREAKMXXNCOA-UHFFFAOYSA-N 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 229960002447 thiram Drugs 0.000 description 1
- KUAZQDVKQLNFPE-UHFFFAOYSA-N thiram Chemical compound CN(C)C(=S)SSC(=S)N(C)C KUAZQDVKQLNFPE-UHFFFAOYSA-N 0.000 description 1
- 230000009974 thixotropic effect Effects 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 235000010215 titanium dioxide Nutrition 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 108700012359 toxins Proteins 0.000 description 1
- YWSCPYYRJXKUDB-KAKFPZCNSA-N tralomethrin Chemical compound CC1(C)[C@@H](C(Br)C(Br)(Br)Br)[C@H]1C(=O)O[C@H](C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 YWSCPYYRJXKUDB-KAKFPZCNSA-N 0.000 description 1
- XQJQCBDIXRIYRP-STQMWFEESA-N trans-(1S,2R)-sedaxane Chemical compound FC(F)C1=NN(C)C=C1C(=O)NC1=CC=CC=C1[C@H]1[C@H](C2CC2)C1 XQJQCBDIXRIYRP-STQMWFEESA-N 0.000 description 1
- 230000032258 transport Effects 0.000 description 1
- ILJSQTXMGCGYMG-UHFFFAOYSA-N triacetic acid Chemical compound CC(=O)CC(=O)CC(O)=O ILJSQTXMGCGYMG-UHFFFAOYSA-N 0.000 description 1
- 150000003626 triacylglycerols Chemical class 0.000 description 1
- 230000004102 tricarboxylic acid cycle Effects 0.000 description 1
- DQJCHOQLCLEDLL-UHFFFAOYSA-N tricyclazole Chemical compound CC1=CC=CC2=C1N1C=NN=C1S2 DQJCHOQLCLEDLL-UHFFFAOYSA-N 0.000 description 1
- 229940087291 tridecyl alcohol Drugs 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- XAIPTRIXGHTTNT-UHFFFAOYSA-N triflumuron Chemical compound C1=CC(OC(F)(F)F)=CC=C1NC(=O)NC(=O)C1=CC=CC=C1Cl XAIPTRIXGHTTNT-UHFFFAOYSA-N 0.000 description 1
- PQDJYEQOELDLCP-UHFFFAOYSA-N trimethylsilane Chemical group C[SiH](C)C PQDJYEQOELDLCP-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 108010013280 ubiquinol oxidase Proteins 0.000 description 1
- 241000701447 unidentified baculovirus Species 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- DRTQHJPVMGBUCF-UHFFFAOYSA-N uracil arabinoside Natural products OC1C(O)C(CO)OC1N1C(=O)NC(=O)C=C1 DRTQHJPVMGBUCF-UHFFFAOYSA-N 0.000 description 1
- 229940045145 uridine Drugs 0.000 description 1
- 229940005605 valeric acid Drugs 0.000 description 1
- JARYYMUOCXVXNK-IMTORBKUSA-N validamycin Chemical compound N([C@H]1C[C@@H]([C@H]([C@H](O)[C@H]1O)O[C@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)O)CO)[C@H]1C=C(CO)[C@H](O)[C@H](O)[C@H]1O JARYYMUOCXVXNK-IMTORBKUSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- 239000004562 water dispersible granule Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- 235000014692 zinc oxide Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
-
- 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
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
- A01N47/18—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing a —O—CO—N< group, or a thio analogue thereof, directly attached to a heterocyclic or cycloaliphatic ring
-
- 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
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D411/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen and sulfur atoms as the only ring hetero atoms
- C07D411/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen and sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D411/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen and sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Dentistry (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Agronomy & Crop Science (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US25599609P | 2009-10-29 | 2009-10-29 | |
| US61/255,996 | 2009-10-29 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR20120112423A true KR20120112423A (ko) | 2012-10-11 |
Family
ID=43548802
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020127013672A Withdrawn KR20120112423A (ko) | 2009-10-29 | 2010-10-12 | 복소환식 이환 치환된 아졸릴 벤젠 살진균제 |
Country Status (25)
| Country | Link |
|---|---|
| US (1) | US8921360B2 (https=) |
| EP (1) | EP2493880B1 (https=) |
| JP (1) | JP2013509408A (https=) |
| KR (1) | KR20120112423A (https=) |
| CN (1) | CN102596940B (https=) |
| AR (1) | AR078830A1 (https=) |
| AU (1) | AU2010318557A1 (https=) |
| BR (1) | BR112012009998A2 (https=) |
| CA (1) | CA2790361A1 (https=) |
| CL (1) | CL2012001071A1 (https=) |
| CO (1) | CO6551700A2 (https=) |
| ES (1) | ES2435298T3 (https=) |
| GE (1) | GEP20135951B (https=) |
| IL (1) | IL218942A0 (https=) |
| IN (1) | IN2012DN02871A (https=) |
| MX (1) | MX2012004808A (https=) |
| NZ (1) | NZ599070A (https=) |
| PE (1) | PE20121357A1 (https=) |
| PH (1) | PH12012500749A1 (https=) |
| PL (1) | PL2493880T3 (https=) |
| RU (1) | RU2012122017A (https=) |
| TW (1) | TW201116212A (https=) |
| UY (1) | UY32983A (https=) |
| WO (1) | WO2011059619A1 (https=) |
| ZA (1) | ZA201202421B (https=) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL271149B2 (en) * | 2017-06-14 | 2024-05-01 | Trevena Inc | Compounds for modulating s1p1 activity and methods of using the same |
| TWI832917B (zh) * | 2018-11-06 | 2024-02-21 | 美商富曼西公司 | 經取代之甲苯基殺真菌劑 |
| EP4061352A4 (en) | 2019-11-19 | 2024-02-28 | Trevena, Inc. | COMPOUNDS AND METHODS FOR PRODUCING S1P1-MODULATING COMPOUNDS |
| PY2133975A (es) | 2020-05-06 | 2022-01-19 | Fmc Corp | Fungicidas de tolilo sustituido y sus mezclas |
| CN116768876B (zh) * | 2022-03-10 | 2025-08-15 | 河北大学 | 一种含二氢苯并呋喃基的异噁唑类化合物及其制备方法与应用 |
| CN116768875B (zh) * | 2022-03-10 | 2025-08-15 | 河北大学 | 一种含二氢苯并呋喃基的异噁唑啉类化合物及其制备方法与应用 |
Family Cites Families (34)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2891855A (en) | 1954-08-16 | 1959-06-23 | Geigy Ag J R | Compositions and methods for influencing the growth of plants |
| US3235361A (en) | 1962-10-29 | 1966-02-15 | Du Pont | Method for the control of undesirable vegetation |
| US3060084A (en) | 1961-06-09 | 1962-10-23 | Du Pont | Improved homogeneous, readily dispersed, pesticidal concentrate |
| US3299566A (en) | 1964-06-01 | 1967-01-24 | Olin Mathieson | Water soluble film containing agricultural chemicals |
| US3309192A (en) | 1964-12-02 | 1967-03-14 | Du Pont | Method of controlling seedling weed grasses |
| US4144050A (en) | 1969-02-05 | 1979-03-13 | Hoechst Aktiengesellschaft | Micro granules for pesticides and process for their manufacture |
| US3920442A (en) | 1972-09-18 | 1975-11-18 | Du Pont | Water-dispersible pesticide aggregates |
| US4172714A (en) | 1976-12-20 | 1979-10-30 | E. I. Du Pont De Nemours And Company | Dry compactible, swellable herbicidal compositions and pellets produced therefrom |
| GB2095558B (en) | 1981-03-30 | 1984-10-24 | Avon Packers Ltd | Formulation of agricultural chemicals |
| DE3246493A1 (de) | 1982-12-16 | 1984-06-20 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung von wasserdispergierbaren granulaten |
| US5180587A (en) | 1988-06-28 | 1993-01-19 | E. I. Du Pont De Nemours And Company | Tablet formulations of pesticides |
| DE69033861T2 (de) | 1989-08-30 | 2002-06-06 | Kynoch Agrochemicals (Proprietary) Ltd., Sandton | Herstellung eines Dosierungsmittels |
| ES2065680T3 (es) | 1990-03-12 | 1995-02-16 | Du Pont | Granulos de plaguicida dispersables en agua o solubles en agua a partir de aglutinantes activados por calor. |
| EP0480679B1 (en) | 1990-10-11 | 1996-09-18 | Sumitomo Chemical Company Limited | Pesticidal composition |
| SK140295A3 (en) | 1993-05-12 | 1996-09-04 | Du Pont | Condensed bicyclic pyrimidinones, fungicidal agents on their base and inhibition method of plant deseases by using them |
| BR9609613A (pt) | 1995-07-05 | 1999-05-25 | Du Pont | Composto composição fungicida e método de controle de doenças de plantas |
| ATE216999T1 (de) | 1996-03-11 | 2002-05-15 | Syngenta Participations Ag | Pyrimidin-4-on derivate als pestizidesmittel |
| GB9709317D0 (en) * | 1997-05-09 | 1997-06-25 | Agrevo Uk Ltd | Fungicides |
| GB9719411D0 (en) | 1997-09-12 | 1997-11-12 | Ciba Geigy Ag | New Pesticides |
| DE69915472T2 (de) | 1998-06-04 | 2004-08-19 | Kumiai Chemical Industry Co., Ltd. | Phenylacetylenderivate und bakterizide für landwirtschaft und gartenbau |
| EP1403256A4 (en) | 2001-06-05 | 2004-10-20 | Fujisawa Pharmaceutical Co | FUSED IMIDAZOLE DERIVATIVE |
| DE10136065A1 (de) | 2001-07-25 | 2003-02-13 | Bayer Cropscience Ag | Pyrazolylcarboxanilide |
| TWI283164B (en) | 2001-09-21 | 2007-07-01 | Du Pont | Anthranilamide arthropodicide treatment |
| TW200301698A (en) | 2001-12-21 | 2003-07-16 | Bristol Myers Squibb Co | Acridone inhibitors of IMPDH enzyme |
| WO2004037770A1 (ja) | 2002-10-23 | 2004-05-06 | Nippon Soda Co.,Ltd. | ヒドラジン誘導体、製造中間体および農園芸用殺菌剤および殺虫剤 |
| KR101066433B1 (ko) | 2002-12-26 | 2011-09-23 | 이하라케미칼 고교가부시키가이샤 | 벤질아민 유도체 제조방법 |
| JP4451849B2 (ja) * | 2003-11-28 | 2010-04-14 | 日本曹達株式会社 | アリール複素環誘導体および農園芸用殺菌剤および殺虫剤 |
| US7241773B2 (en) | 2003-12-22 | 2007-07-10 | Abbott Laboratories | 3-quinuclidinyl heteroatom bridged biaryl derivatives |
| EP1746099A1 (en) | 2004-12-23 | 2007-01-24 | DeveloGen Aktiengesellschaft | Mnk1 or Mnk2 inhibitors |
| JP2006327973A (ja) * | 2005-05-25 | 2006-12-07 | Nippon Soda Co Ltd | アリール複素環誘導体および農園芸用殺菌剤 |
| WO2007067511A2 (en) | 2005-12-06 | 2007-06-14 | Merck & Co., Inc. | Morpholine carboxamide prokineticin receptor antagonists |
| WO2008124092A2 (en) | 2007-04-03 | 2008-10-16 | E. I. Du Pont De Nemours And Company | Substituted benzene fungicides |
| EP2005995A1 (en) | 2007-06-22 | 2008-12-24 | Glaxo Group Limited | Heterocyclic compounds for the treatment of tuberculosis |
| CA2705318C (en) | 2007-11-15 | 2013-12-31 | Boehringer Ingelheim International Gmbh | Inhibitors of human immunodeficiency virus replication |
-
2010
- 2010-10-05 TW TW099133915A patent/TW201116212A/zh unknown
- 2010-10-12 CA CA2790361A patent/CA2790361A1/en not_active Abandoned
- 2010-10-12 GE GEAP201012723A patent/GEP20135951B/en unknown
- 2010-10-12 WO PCT/US2010/052228 patent/WO2011059619A1/en not_active Ceased
- 2010-10-12 PE PE2012000569A patent/PE20121357A1/es not_active Application Discontinuation
- 2010-10-12 EP EP10768149.6A patent/EP2493880B1/en active Active
- 2010-10-12 JP JP2012536841A patent/JP2013509408A/ja active Pending
- 2010-10-12 US US13/500,928 patent/US8921360B2/en not_active Expired - Fee Related
- 2010-10-12 RU RU2012122017/04A patent/RU2012122017A/ru unknown
- 2010-10-12 MX MX2012004808A patent/MX2012004808A/es active IP Right Grant
- 2010-10-12 AU AU2010318557A patent/AU2010318557A1/en not_active Abandoned
- 2010-10-12 PL PL10768149T patent/PL2493880T3/pl unknown
- 2010-10-12 PH PH1/2012/500749A patent/PH12012500749A1/en unknown
- 2010-10-12 CN CN201080049706.7A patent/CN102596940B/zh not_active Expired - Fee Related
- 2010-10-12 BR BR112012009998A patent/BR112012009998A2/pt not_active IP Right Cessation
- 2010-10-12 ES ES10768149T patent/ES2435298T3/es active Active
- 2010-10-12 NZ NZ599070A patent/NZ599070A/xx not_active IP Right Cessation
- 2010-10-12 KR KR1020127013672A patent/KR20120112423A/ko not_active Withdrawn
- 2010-10-12 IN IN2871DEN2012 patent/IN2012DN02871A/en unknown
- 2010-10-28 UY UY0001032983A patent/UY32983A/es not_active Application Discontinuation
- 2010-10-29 AR ARP100103996A patent/AR078830A1/es unknown
-
2012
- 2012-03-29 IL IL218942A patent/IL218942A0/en unknown
- 2012-04-03 ZA ZA2012/02421A patent/ZA201202421B/en unknown
- 2012-04-26 CL CL2012001071A patent/CL2012001071A1/es unknown
- 2012-05-22 CO CO12084046A patent/CO6551700A2/es not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| US20120202815A1 (en) | 2012-08-09 |
| EP2493880B1 (en) | 2013-09-18 |
| JP2013509408A (ja) | 2013-03-14 |
| TW201116212A (en) | 2011-05-16 |
| ZA201202421B (en) | 2013-06-26 |
| IL218942A0 (en) | 2012-07-31 |
| PH12012500749A1 (en) | 2012-10-29 |
| NZ599070A (en) | 2013-09-27 |
| CN102596940A (zh) | 2012-07-18 |
| EP2493880A1 (en) | 2012-09-05 |
| PE20121357A1 (es) | 2012-10-15 |
| UY32983A (es) | 2011-05-31 |
| CO6551700A2 (es) | 2012-10-31 |
| AU2010318557A1 (en) | 2012-04-19 |
| US8921360B2 (en) | 2014-12-30 |
| CL2012001071A1 (es) | 2012-09-14 |
| MX2012004808A (es) | 2012-06-14 |
| BR112012009998A2 (pt) | 2019-09-24 |
| AR078830A1 (es) | 2011-12-07 |
| PL2493880T3 (pl) | 2014-02-28 |
| CA2790361A1 (en) | 2011-05-19 |
| GEP20135951B (en) | 2013-10-25 |
| RU2012122017A (ru) | 2013-12-10 |
| ES2435298T3 (es) | 2013-12-18 |
| CN102596940B (zh) | 2015-01-28 |
| IN2012DN02871A (https=) | 2015-07-24 |
| WO2011059619A1 (en) | 2011-05-19 |
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Legal Events
| Date | Code | Title | Description |
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| PA0105 | International application |
Patent event date: 20120525 Patent event code: PA01051R01D Comment text: International Patent Application |
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| PG1501 | Laying open of application | ||
| PC1203 | Withdrawal of no request for examination | ||
| WITN | Application deemed withdrawn, e.g. because no request for examination was filed or no examination fee was paid |