JP2007527887A - 5,6−ジアルキル−7−アミノトリアゾロピリミジン、その調製、および有害真菌を防除するためのその使用、ならびにそれらの化合物を含む組成物 - Google Patents
5,6−ジアルキル−7−アミノトリアゾロピリミジン、その調製、および有害真菌を防除するためのその使用、ならびにそれらの化合物を含む組成物 Download PDFInfo
- Publication number
- JP2007527887A JP2007527887A JP2007502272A JP2007502272A JP2007527887A JP 2007527887 A JP2007527887 A JP 2007527887A JP 2007502272 A JP2007502272 A JP 2007502272A JP 2007502272 A JP2007502272 A JP 2007502272A JP 2007527887 A JP2007527887 A JP 2007527887A
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- JP
- Japan
- Prior art keywords
- formula
- compound
- triazolo
- ylamine
- pyrimidin
- 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.)
- Granted
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- 125000001931 aliphatic group Chemical group 0.000 claims abstract description 4
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract description 4
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- MYSOIJJLHFVDAP-UHFFFAOYSA-N 5-ethyl-6-heptyl-[1,2,4]triazolo[1,5-a]pyrimidin-7-amine Chemical compound NC1=C(CCCCCCC)C(CC)=NC2=NC=NN21 MYSOIJJLHFVDAP-UHFFFAOYSA-N 0.000 claims 1
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- VZPSVWCBFLVGJD-UHFFFAOYSA-N 5-ethyl-6-undecyl-[1,2,4]triazolo[1,5-a]pyrimidin-7-amine Chemical compound NC1=C(CCCCCCCCCCC)C(CC)=NC2=NC=NN21 VZPSVWCBFLVGJD-UHFFFAOYSA-N 0.000 claims 1
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- 239000000395 magnesium oxide Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- CRGZYKWWYNQGEC-UHFFFAOYSA-N magnesium;methanolate Chemical compound [Mg+2].[O-]C.[O-]C CRGZYKWWYNQGEC-UHFFFAOYSA-N 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- YKSNLCVSTHTHJA-UHFFFAOYSA-L maneb Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S YKSNLCVSTHTHJA-UHFFFAOYSA-L 0.000 description 1
- 229920000940 maneb Polymers 0.000 description 1
- CIFWZNRJIBNXRE-UHFFFAOYSA-N mepanipyrim Chemical compound CC#CC1=CC(C)=NC(NC=2C=CC=CC=2)=N1 CIFWZNRJIBNXRE-UHFFFAOYSA-N 0.000 description 1
- BCTQJXQXJVLSIG-UHFFFAOYSA-N mepronil Chemical compound CC(C)OC1=CC=CC(NC(=O)C=2C(=CC=CC=2)C)=C1 BCTQJXQXJVLSIG-UHFFFAOYSA-N 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- HYVVJDQGXFXBRZ-UHFFFAOYSA-N metam Chemical compound CNC(S)=S HYVVJDQGXFXBRZ-UHFFFAOYSA-N 0.000 description 1
- XWPZUHJBOLQNMN-UHFFFAOYSA-N metconazole Chemical compound C1=NC=NN1CC1(O)C(C)(C)CCC1CC1=CC=C(Cl)C=C1 XWPZUHJBOLQNMN-UHFFFAOYSA-N 0.000 description 1
- ZQEIXNIJLIKNTD-UHFFFAOYSA-N methyl N-(2,6-dimethylphenyl)-N-(methoxyacetyl)alaninate Chemical compound COCC(=O)N(C(C)C(=O)OC)C1=C(C)C=CC=C1C ZQEIXNIJLIKNTD-UHFFFAOYSA-N 0.000 description 1
- CJPQIRJHIZUAQP-UHFFFAOYSA-N methyl N-(2,6-dimethylphenyl)-N-(phenylacetyl)alaninate Chemical compound CC=1C=CC=C(C)C=1N(C(C)C(=O)OC)C(=O)CC1=CC=CC=C1 CJPQIRJHIZUAQP-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 125000002950 monocyclic group Chemical group 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- 125000003136 n-heptyl 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])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- UQJQVUOTMVCFHX-UHFFFAOYSA-L nabam Chemical compound [Na+].[Na+].[S-]C(=S)NCCNC([S-])=S UQJQVUOTMVCFHX-UHFFFAOYSA-L 0.000 description 1
- 239000004311 natamycin Substances 0.000 description 1
- NCXMLFZGDNKEPB-FFPOYIOWSA-N natamycin Chemical compound O[C@H]1[C@@H](N)[C@H](O)[C@@H](C)O[C@H]1O[C@H]1/C=C/C=C/C=C/C=C/C[C@@H](C)OC(=O)/C=C/[C@H]2O[C@@H]2C[C@H](O)C[C@](O)(C[C@H](O)[C@H]2C(O)=O)O[C@H]2C1 NCXMLFZGDNKEPB-FFPOYIOWSA-N 0.000 description 1
- 229960003255 natamycin Drugs 0.000 description 1
- 235000010298 natamycin Nutrition 0.000 description 1
- 125000006501 nitrophenyl group Chemical group 0.000 description 1
- 125000006611 nonyloxy group Chemical group 0.000 description 1
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 150000002902 organometallic compounds Chemical class 0.000 description 1
- JHIPUJPTQJYEQK-ZLHHXESBSA-N orysastrobin Chemical compound CNC(=O)C(=N\OC)\C1=CC=CC=C1CO\N=C(/C)\C(=N\OC)\C(\C)=N\OC JHIPUJPTQJYEQK-ZLHHXESBSA-N 0.000 description 1
- UWVQIROCRJWDKL-UHFFFAOYSA-N oxadixyl Chemical compound CC=1C=CC=C(C)C=1N(C(=O)COC)N1CCOC1=O UWVQIROCRJWDKL-UHFFFAOYSA-N 0.000 description 1
- AMEKQAFGQBKLKX-UHFFFAOYSA-N oxycarboxin Chemical compound O=S1(=O)CCOC(C)=C1C(=O)NC1=CC=CC=C1 AMEKQAFGQBKLKX-UHFFFAOYSA-N 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 239000000123 paper Substances 0.000 description 1
- 230000002688 persistence Effects 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 229940044654 phenolsulfonic acid Drugs 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- IBSNKSODLGJUMQ-SDNWHVSQSA-N picoxystrobin Chemical compound CO\C=C(\C(=O)OC)C1=CC=CC=C1COC1=CC=CC(C(F)(F)F)=N1 IBSNKSODLGJUMQ-SDNWHVSQSA-N 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- YEBIHIICWDDQOL-YBHNRIQQSA-N polyoxin Polymers O[C@@H]1[C@H](O)[C@@H](C(C=O)N)O[C@H]1N1C(=O)NC(=O)C(C(O)=O)=C1 YEBIHIICWDDQOL-YBHNRIQQSA-N 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 238000004321 preservation Methods 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- TVLSRXXIMLFWEO-UHFFFAOYSA-N prochloraz Chemical compound C1=CN=CN1C(=O)N(CCC)CCOC1=C(Cl)C=C(Cl)C=C1Cl TVLSRXXIMLFWEO-UHFFFAOYSA-N 0.000 description 1
- QXJKBPAVAHBARF-BETUJISGSA-N procymidone Chemical compound O=C([C@]1(C)C[C@@]1(C1=O)C)N1C1=CC(Cl)=CC(Cl)=C1 QXJKBPAVAHBARF-BETUJISGSA-N 0.000 description 1
- STJLVHWMYQXCPB-UHFFFAOYSA-N propiconazole Chemical compound O1C(CCC)COC1(C=1C(=CC(Cl)=CC=1)Cl)CN1N=CN=C1 STJLVHWMYQXCPB-UHFFFAOYSA-N 0.000 description 1
- KKMLIVYBGSAJPM-UHFFFAOYSA-L propineb Chemical compound [Zn+2].[S-]C(=S)NC(C)CNC([S-])=S KKMLIVYBGSAJPM-UHFFFAOYSA-L 0.000 description 1
- 125000006233 propoxy propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])OC([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000006225 propoxyethyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
- FLVBXVXXXMLMOX-UHFFFAOYSA-N proquinazid Chemical compound C1=C(I)C=C2C(=O)N(CCC)C(OCCC)=NC2=C1 FLVBXVXXXMLMOX-UHFFFAOYSA-N 0.000 description 1
- HZRSNVGNWUDEFX-UHFFFAOYSA-N pyraclostrobin Chemical compound COC(=O)N(OC)C1=CC=CC=C1COC1=NN(C=2C=CC(Cl)=CC=2)C=C1 HZRSNVGNWUDEFX-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- ZLIBICFPKPWGIZ-UHFFFAOYSA-N pyrimethanil Chemical compound CC1=CC(C)=NC(NC=2C=CC=CC=2)=N1 ZLIBICFPKPWGIZ-UHFFFAOYSA-N 0.000 description 1
- XRJLAOUDSILTFT-UHFFFAOYSA-N pyroquilon Chemical compound O=C1CCC2=CC=CC3=C2N1CC3 XRJLAOUDSILTFT-UHFFFAOYSA-N 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- WRPIRSINYZBGPK-UHFFFAOYSA-N quinoxyfen Chemical compound C1=CC(F)=CC=C1OC1=CC=NC2=CC(Cl)=CC(Cl)=C12 WRPIRSINYZBGPK-UHFFFAOYSA-N 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 235000012045 salad Nutrition 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- MXMXHPPIGKYTAR-UHFFFAOYSA-N silthiofam Chemical compound CC=1SC([Si](C)(C)C)=C(C(=O)NCC=C)C=1C MXMXHPPIGKYTAR-UHFFFAOYSA-N 0.000 description 1
- 239000004550 soluble concentrate Substances 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- PUYXTUJWRLOUCW-UHFFFAOYSA-N spiroxamine Chemical compound O1C(CN(CC)CCC)COC11CCC(C(C)(C)C)CC1 PUYXTUJWRLOUCW-UHFFFAOYSA-N 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000001694 spray drying Methods 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 235000021012 strawberries Nutrition 0.000 description 1
- 229960005322 streptomycin Drugs 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 150000003447 sulfenic acid derivatives Chemical class 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- GFYHSKONPJXCDE-UHFFFAOYSA-N sym-collidine Natural products CC1=CN=C(C)C(C)=C1 GFYHSKONPJXCDE-UHFFFAOYSA-N 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- LITQZINTSYBKIU-UHFFFAOYSA-F tetracopper;hexahydroxide;sulfate Chemical compound [OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[Cu+2].[Cu+2].[Cu+2].[Cu+2].[O-]S([O-])(=O)=O LITQZINTSYBKIU-UHFFFAOYSA-F 0.000 description 1
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 239000004308 thiabendazole Substances 0.000 description 1
- 235000010296 thiabendazole Nutrition 0.000 description 1
- WJCNZQLZVWNLKY-UHFFFAOYSA-N thiabendazole Chemical compound S1C=NC(C=2NC3=CC=CC=C3N=2)=C1 WJCNZQLZVWNLKY-UHFFFAOYSA-N 0.000 description 1
- 229960004546 thiabendazole Drugs 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
- 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
- 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
- VJQYLJSMBWXGDV-UHFFFAOYSA-N tiadinil Chemical compound N1=NSC(C(=O)NC=2C=C(Cl)C(C)=CC=2)=C1C VJQYLJSMBWXGDV-UHFFFAOYSA-N 0.000 description 1
- HYVWIQDYBVKITD-UHFFFAOYSA-N tolylfluanid Chemical compound CN(C)S(=O)(=O)N(SC(F)(Cl)Cl)C1=CC=C(C)C=C1 HYVWIQDYBVKITD-UHFFFAOYSA-N 0.000 description 1
- APEJMQOBVMLION-VOTSOKGWSA-N trans-cinnamamide Chemical compound NC(=O)\C=C\C1=CC=CC=C1 APEJMQOBVMLION-VOTSOKGWSA-N 0.000 description 1
- BAZVSMNPJJMILC-UHFFFAOYSA-N triadimenol Chemical compound C1=NC=NN1C(C(O)C(C)(C)C)OC1=CC=C(Cl)C=C1 BAZVSMNPJJMILC-UHFFFAOYSA-N 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- DQJCHOQLCLEDLL-UHFFFAOYSA-N tricyclazole Chemical compound CC1=CC=CC2=C1N1C=NN=C1S2 DQJCHOQLCLEDLL-UHFFFAOYSA-N 0.000 description 1
- ONCZDRURRATYFI-TVJDWZFNSA-N trifloxystrobin Chemical compound CO\N=C(\C(=O)OC)C1=CC=CC=C1CO\N=C(/C)C1=CC=CC(C(F)(F)F)=C1 ONCZDRURRATYFI-TVJDWZFNSA-N 0.000 description 1
- HSMVPDGQOIQYSR-KGENOOAVSA-N triflumizole Chemical compound C1=CN=CN1C(/COCCC)=N/C1=CC=C(Cl)C=C1C(F)(F)F HSMVPDGQOIQYSR-KGENOOAVSA-N 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- RROQIUMZODEXOR-UHFFFAOYSA-N triforine Chemical compound O=CNC(C(Cl)(Cl)Cl)N1CCN(C(NC=O)C(Cl)(Cl)Cl)CC1 RROQIUMZODEXOR-UHFFFAOYSA-N 0.000 description 1
- RKBCYCFRFCNLTO-UHFFFAOYSA-N triisopropylamine Chemical compound CC(C)N(C(C)C)C(C)C RKBCYCFRFCNLTO-UHFFFAOYSA-N 0.000 description 1
- 238000009827 uniform distribution Methods 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000004562 water dispersible granule Substances 0.000 description 1
- 239000004552 water soluble powder Substances 0.000 description 1
- 239000003021 water soluble solvent Substances 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
- DUBNHZYBDBBJHD-UHFFFAOYSA-L ziram Chemical compound [Zn+2].CN(C)C([S-])=S.CN(C)C([S-])=S DUBNHZYBDBBJHD-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Agronomy & Crop Science (AREA)
- General Health & Medical Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Catching Or Destruction (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Description
R1は、C5-C12-アルキルまたはC5-C14-アルコキシアルキルであり、ここで、脂肪族基は、1〜3個の以下の基:シアノ、ニトロ、ヒドロキシル、C3-C6-シクロアルキル、C1-C6-アルキルチオおよびNRaRbにより置換されていてもよく;
Ra、Rbは、水素またはC1-C6-アルキルであり;
R2は、CHR3CH3、シクロプロピル、CH=CH2またはCH2CH=CH2であり;
R3は、水素、CH3またはCH2CH3である)
で表される5,6-ジアルキル-7-アミノトリアゾロピリミジンに関する。
アルキル:1〜4個または5〜12個の炭素原子を有している飽和直鎖または一分枝状もしくは二分枝状の炭化水素基、例えばC1-C6-アルキルで、メチル、エチル、プロピル、1-メチルエチル、ブチル、1-メチルプロピル、2-メチルプロピル、1,1-ジメチルエチル、n-ペンチル、1-メチルブチル、2-メチルブチル、3-メチルブチル、2,2-ジメチルプロピル、1-エチルプロピル、ヘキシル、1,1-ジメチルプロピル、1,2-ジメチルプロピル、1-メチルペンチル、2-メチルペンチル、3-メチルペンチル、4-メチルペンチル、1,1-ジメチルブチル、1,2-ジメチルブチル、1,3-ジメチルブチル、2,2-ジメチルブチル、2,3-ジメチルブチル、3,3-ジメチルブチル、1-エチルブチル、2-エチルブチル、1,1,2-トリメチルプロピル、1,2,2-トリメチルプロピル、1-エチル-1-メチルプロピル、および1-エチル-2-メチルプロピルなど;
ハロメチル:メチル基で、この場合、水素原子の一部または全部が上で記載したハロゲン原子により置換されていてもよいもの;特にクロロメチル、ブロモメチル、ジクロロメチル、トリクロロメチル、フルオロメチル、ジフルオロメチル、トリフルオロメチル、クロロフルオロメチル、ジクロロフルオロメチル、クロロジフルオロメチル;
シクロアルキル:3〜6個の炭素環構成員を有する単環式または二環式飽和炭化水素基で、例えばシクロプロピル、シクロブチル、シクロペンチルおよびシクロヘキシル;
アルコキシアルキル:酸素原子によって分断されている飽和直鎖、あるいは一分枝、二分枝もしくは三分枝状の炭化水素鎖で、例えばC5-C12-アルコキシアルキル:任意の位置で酸素原子によって分断されていてもよい5〜12個の炭素原子を有している上に記載した炭化水素鎖、例えばプロポキシエチル、ブトキシエチル、ペントキシエチル、ヘキシルオキシエチル、ヘプチルオキシエチル、オクチルオキシエチル、ノニルオキシ、3-(3-エチルヘキシルオキシ)エチル、3-(2,4,4-トリメチルペンチルオキシ)エチル、3-(1-エチル-3-メチルブトキシ)エチル、エトキシプロピル、プロポキシプロピル、ブトキシプロピル、ペントキシプロピル、ヘキシルオキシプロピル、ヘプチルオキシプロピル、オクチルオキシプロピル、ノニルオキシプロピル、3-(3-エチルヘキシルオキシ)プロピル、3-(2,4,4-トリメチルペンチルオキシ)プロピル、3-(1-エチル-3-メチルブトキシ)プロピル、エトキシブチル、プロポキシブチル、ブトキシブチル、ペントキシブチル、ヘキシルオキシブチル、ヘプチルオキシブチル、オクチルオキシブチル、ノニルオキシブチル、3-(3-エチルヘキシルオキシ)ブチル、3-(2,4,4-トリメチルペンチルオキシ)ブチル、3-(1-エチル-3-メチルブトキシ)ブチル、メトキシペンチル、エトキシペンチル、プロポキシペンチル、ブトキシペンチル、ペントキシペンチル、ヘキシルオキシペンチル、ヘプチルオキシペンチル、3-(3-メチルヘキシルオキシ)ペンチル、3-(2,4-ジメチルペンチルオキシ)ペンチル、3-(1-エチル-3-メチルブトキシ)ペンチル。
により表される。
各化合物に関するR1が表Aの1つの行に対応し、R2がエチルである、式Iの化合物。
各化合物に関するR1が表Aの1つの行に対応し、R2がイソプロピルである、式Iの化合物。
各化合物に関するR1が表Aの1つの行に対応し、R2が1-メチルプロピルである、式Iの化合物。
各化合物に関するR1が表Aの1つの行に対応し、R2がエテニルである、式Iの化合物。
各化合物に関するR1が表Aの1つの行に対応し、R2がアリルである、式Iの化合物。
・ 禾穀類、イネおよび芝生につくビポラリス種(Bipolaris species)およびドレクスレラ種(Drechslera species)、
・ 禾穀類につくブルメリア・グラミニス(Blumeria graminis)(ウドンコ病)、
・ イチゴ、野菜、観葉植物、およびブドウの木につくボトリチス・シネレア(Botrytis cinerea)(灰色カビ病)、
・ サラダ用野菜につくブレミア・ラクツカ(Bremia lactucae)、
・ ウリ科植物につくエリシフェ・シコラセアルム(Erysiphe cichoracearum)およびスファエロテカ・フリギネア(Sphaerotheca fuliginea)、
・ 様々な植物につくフサリウム種(Fusarium species)およびベルチシリウム種(Verticillium species)、
・ 禾穀類、バナナおよびラッカセイにつくマイコスファエレラ種(Mycosphaerella species)、
・ キャベツおよびタマネギにつくペロノスポラ種(Peronospora species)、
・ ダイズにつくファコプソラ・パキリジ(Phakopsora pachyrhizi)およびファコプソラ・メイボミア(P. meibomiae)、
・ ジャガイモおよびトマトにつくフィトフトラ・インフェスタンス(Phytophthora infestans)、
・ コショウにつくフィトフトラ・カプシシ(Phytophthora capsici)、
・ ブドウの木につくプラスモパラ・ビチコーラ(Plasmopara viticola)、
・ リンゴの木につくポドスファエラ・ロイコトリカ(Podosphaera leucotricha)、
・ コムギおよびオオムギにつくシュードセルコスポレラ・ヘルポトリコイデス(Pseudocercosporella herpotrichoides)、
・ ホップおよびキュウリにつくシュードペロノスポラ種(Pseudoperonospora species)、
・ 禾穀類につくプッシニア種(Puccinia species)、
・ イネにつくピリクラリア・オリザエ(Pyricularia oryzae)、
・ 芝生につくピチウム・アファニデルマツム(Pythium aphanidermatum)、
・ ワタ、イネおよび芝生につくリゾクトニア種(Rhizoctonia species)、
・ コムギにつくセプトリア・トリチシ(Septoria tritici)およびスタゴノスポラ・ノドラム(Stagonospora nodorum)、
・ ブドウの木につくウンシヌラ・ネカトール(Uncinula necator)、
・ 禾穀類およびサトウキビにつくウスチラゴ種(Ustilago species)、
・ リンゴの木およびナシの木につくベンチュリア種(Venturia species)(黒星病)。
A) 水溶性濃縮物(SL)
10重量部の本発明の化合物を水または水溶性溶媒に溶解する。あるいは、湿潤剤または他の添加剤を加える。活性化合物は水により希釈すると溶解する。
20重量部の本発明の化合物を、分散剤、たとえばポリビニルピロリドンを加えてシクロヘキサノンに溶解する。水により希釈すると分散物が得られる。
15重量部の本発明の化合物を、ドデシルベンゼンスルホン酸カルシウムおよびエトキシル化ひまし油(それぞれ5%)を加えてキシレンに溶解する。水により希釈するとエマルションが得られる。
40重量部の本発明の化合物をドデシルベンゼンスルホン酸カルシウムおよびエトキシル化ひまし油(それぞれ5%)を加えてキシレンに溶解する。この混合物を乳化器(Ultraturrax)を用いて水中に導入し、均一なエマルションを調製する。水により希釈するとエマルションが得られる。
撹拌したボールミル中で、20重量部の本発明の化合物を、分散剤、湿潤剤および水または有機溶媒を加えて粉砕すると、微細な活性化合物の懸濁液が得られる。水により希釈すると、活性化合物の安定な懸濁液が得られる。
50重量部の本発明の化合物を、分散剤および湿潤剤を加えて微細に粉砕し、技術機器(たとえば、射出機、噴霧塔、流動床)を用いて水分散性または水溶性顆粒を調製する。水により希釈すると活性化合物の安定な分散物または溶液が得られる。
75重量部の本発明の化合物を、分散剤、湿潤剤およびシリカゲルを加えてローターステーターミル(rotor-stator mill)中で粉砕する。水により希釈すると活性化合物の安定な分散物または溶液が得られる。
H) 散粉用製品(DP)
5重量部の本発明の化合物を微細に粉砕し、95%の微細に粉砕したカオリンと緊密に混合する。これにより散布用製品が得られる。
0.5重量部の本発明の化合物を微細に粉砕し、95.5%の担体と結合させる。最新の方法は射出、噴霧乾燥または流動床である。これにより無希釈で施用される顆粒が得られる。
10重量部の本発明の化合物を有機溶媒、たとえばキシレンに溶解する。これにより無希釈で施用される製品が得られる。
・アルジモルフ(aldimorph)、ドジン(dodine)、ドデモルフ(dodemorph)、フェンプロピモルフ(fenpropimorph)、フェンプロピジン(fenpropidin)、グアザチン(guazatine)、イミノクタジン(iminoctadine)、スピロキサミン(spiroxamine)またはトリデモルフ(tridemorph)などのアミン誘導体、
・ピリメタニル(pyrimethanil)、メパニピリム(mepanipyrim)またはシプロジニル(cyprodinyl)などのアニリノピリミジン、
・シクロヘキシミド(cycloheximide)、グリセオフルビン(griseofulvin)、カスガマイシン(kasugamycin)、ナタマイシン(natamycin)、ポリオキシン(polyoxin)またはストレプトマイシン(streptomycin)などの抗生物質、
・ビテルタノール(bitertanol)、ブロモコナゾール(bromoconazole)、シプロコナゾール(cyproconazole)、ジフェノコナゾール(difenoconazole)、ジニトロコナゾール(dinitroconazole)、エニルコナゾール(enilconazole)、エポキシコナゾール(epoxiconazole)、フェンブコナゾール(fenbuconazole)、フルキコナゾール(fluquinconazole)、フルシラゾール(flusilazole)、ヘキサコナゾール(hexaconazole)、イマザリル(imazalil)、メトコナゾール(metconazole)、ミクロブタニル(myclobutanil)、ペンコナゾール(penconazole)、プロピコナゾール(propiconazole)、プロクロラズ(prochloraz)、プロチオコナゾール(prothioconazole)、テブコナゾール(tebuconazole)、トリアジメホン(triadimefon)、トリアジメノール(triadimenol)、トリフルミゾール(triflumizole)またはトリチコナゾール(triticonazole)などのアゾール、
・イプロジオン(iprodione)、ミクロゾリン(myclozolin)、プロシミドン(procymidone)またはビンクロゾリン(vinclozolin)などのジカルボキシミド、
・フェルバム(ferbam)、ナバム(nabam)、マネブ(maneb)、マンコゼブ(mancozeb)、メタム(metam)、メチラム(metiram)、プロピネブ(propineb)、ポリカルバメート(polycarbamate)、チラム(thiram)、ジラム(ziram)またはジネブ(zineb)などのジチオカルバメート、
・アニラジン(anilazine)、ベノミル(benomyl)、ボスカリド(boscalid)、カルベンダジム(carbendazim)、カルボキシン(carboxin)、オキシカルボキシン(oxycarboxin)、シアゾファミド(cyazofamid)、ダゾメット(dazomet)、ジチアノン(dithianon)、ファモキサドン(famoxadone)、フェンアミドン(fenamidone)、フェナリモール(fenarimol)、フベリダゾール(fuberidazole)、フルトラニル(flutolanil)、フラメトピル(furametpyr)、イソプロチオラン(isoprothiolane)、メプロニル(mepronil)、ヌアリモール(nuarimol)、プロベナゾール(probenazole)、プロキナジド(proquinazid)、ピリフェノックス(pyrifenox)、ピロキロン(pyroquilon)、キノキシフェン(quinoxyfen)、シルチオファム(silthiofam)、チアベンダゾール(thiabendazole)、チフルザミド(thifluzamide)、チオファネートメチル(thiophanate-methyl)、チアジニル(tiadinil)、トリシクラゾール(tricyclazole)またはトリフォリン(triforine)などの複素環式化合物、
・ボルドー液、酢酸銅、オキシ塩化銅または塩基性硫酸銅などの銅殺菌剤、
・ビナパクリル(binapacryl)、ジノカップ(dinocap)、ジノブトン(dinobuton)またはニトロフタル-イソプロピル(nitrophthal-isopropyl)などのニトロフェニル誘導体、
・フェンピクロニル(fenpiclonil)またはフルジオキソニル(fludioxonil)などのフェニルピロール、
・硫黄、
・アシベンゾラル-S-メチル(acibenzolar-S-methyl)、ベンチアカリバルブ(benthiavalicarb)、カルプロパミド(carpropamid)、クロロタロニル(chlorothalonil)、シフルフェナミド(cyflufenamid)、シモキサニル(cymoxanil)、ジクロメジン(diclomezine)、ジクロシメット(diclocymet)、ジエトフェンカルブ(diethofencarb)、エジフェンホス(edifenphos)、エタボキサム(ethaboxam)、フェンヘキサミド(fenhexamid)、酢酸フェンチン(fentin acetate)、フェノキサニル(fenoxanil)、フェリムゾン(ferimzone)、フルアジナム(fluazinam)、亜リン酸、フォセチル(fosetyl)、フォセチル-アルミニウム(fosetyl-aluminum)、イプロバリカルブ(iprovalicarb)、ヘキサクロロベンゼン(hexachlorobenzene)、メトラフェノン(metrafenone)、ペンシクロン(pencycuron)、プロパモカルブ(propamocarb)、フタリド(phthalide)、トリクロフォス-メチル(tolclofos-methyl)、キントゼン(tolclofos-methyl)またはゾキサミド(zoxamide)などの他の殺菌剤、
・アゾキシストロビン(azoxystrobin)、ジモキシストロビン(dimoxystrobin)、エネストロブリン(enestroburin)、フルオキサストロビン(fluoxastrobin)、クレソキシム-メチル(kresoxim-methyl)、メトミノストロビン(metominostrobin)、オリサストロビン(orysastrobin)、ピコキシストロビン(picoxystrobin)、ピラクロストロビン(pyraclostrobin)またはトリフロキシストロビン(trifloxystrobin)などのストロビルリン、
・キャプタホール(captafol)、キャプタン(captan)、ジクロフルアニド(dichlofluanid)、フォルペット(folpet)またはトリルフルアニド(tolylfluanid)などのスルフェン酸誘導体、
・ジメトモルフ(dimethomorph)、フルメトベル(flumetover)またはフルモルフ(flumorph)などのシンナミドおよび類似化合物
合成の実施例
出発物質を適当に変更して、以下のこの合成の実施例に記載されている方法を用いてさらなる化合物Iを得た。このようにして得られた化合物は、物性データと共に、以下の表に挙げている。
ヘキサン中のブチルリチウム0.495mol溶液を、-70℃でテトラヒドロフラン(THF)300mlに溶解したデカニトリル0.45molの溶液に加え、混合物を約3時間この温度で撹拌し、次いで、0.45molのプロピオン酸エチルを加えた。続いて、この混合物を約16時間20〜25℃で撹拌し、次に水200mlを加え、希釈HCl溶液を用いて混合物を酸性化した。各相を分離させた後、有機相を除去し、水で洗浄し、乾燥させ、溶媒を除いた。91gの表題化合物が残った。
メシチレン900mlに溶解した1.27molの実施例1の5-シアノウンデカン-3-オンと1.27molの3-アミノ-1,2,4-トリアゾール、および0.25molのp-トルエンスルホン酸の混合物を約4時間170℃で加熱した。約20〜25℃に冷却した後、沈殿物を濾過し、次いで、ジクロロメタンに溶解した。水で洗浄し、乾燥させた後、溶媒を溶液から蒸留除去し、残渣として、m.p.196℃の表題化合物124gを得た。
式Iで表される化合物の抗真菌作用について、以下の実験により検証した。
鉢植えのブドウの木の葉に対し、下記の活性化合物濃度の水性懸濁液を流れ落ちる程度までスプレーした。翌日、葉の下側に、プラスモパラ・ビチコーラの水性胞子懸濁液を接種した。次に、このワインの木を最初に48時間24℃で水蒸気飽和チャンバー内に置いた後、温度20℃〜30℃の温室内に5日間置いた。この期間の後、植物を再び16時間高湿度チャンバー内に置き、胞子嚢柄の出現を促した。次いで、葉の下側の感染の進行程度を目視により測定した。
鉢植えのトマト植物の葉に対し、下記の活性化合物濃度の水性懸濁液を流れ落ちる程度までスプレーした。翌日、葉にフィトフトラ・インフェスタンスの水性胞子懸濁液を接種した。次に、この植物を最初に温度18℃〜20℃の水蒸気飽和チャンバー内に置いた。6日後、未処理で感染させたコントロール植物における葉枯れ病は、感染が%で視覚的に測定可能な程度にまで進行していた。
鉢植えの栽培品種「Muller-Thurgau」のブドウの木の葉に、下記の活性化合物濃度を有している水性懸濁液で流れ落ちる程度までスプレーした。これらの物質の持続性が評価できるように、植物は、スプレーコーティングが乾燥した後、温室内に7日間置いた。その後初めて、葉にプラスモパラ・ビチコーラのの水性胞子懸濁液を接種した。次に、このワインの木を最初に48時間24℃で水蒸気飽和チャンバー内に置いた後、温度20℃〜30℃の温室内に5日または7日間置いた。この期間の後、植物を再度16時間高湿度チャンバー内に置き、胞子嚢柄の出現を促した。次いで、葉の下側の感染の進行程度を目視により測定した。
Claims (13)
- R2がCHR3CH3である、請求項1に記載の式Iで表される化合物。
- R1が、12個以下の炭素原子を有する、非置換の直鎖であるか、あるいは一分枝状、二分枝状または三分岐状のアルキル鎖である、請求項1または2に記載の式Iで表される化合物。
- R2がエチルである、請求項1〜3のいずれか1項に記載の式Iで表される化合物。
- R2がイソプロピルである、請求項1〜3のいずれか1項に記載の式Iで表される化合物。
- R2がCHR3CH3であり、R3が水素、CH3またはCH2CH3である、請求項1〜3のいずれか1項に記載の式Iで表される化合物。
- 5-エチル-6-(1-メチルヘプチル)-[1,2,4]トリアゾロ[1,5-a]ピリミジン-7-イルアミン;
5-エチル-6-オクチル-[1,2,4]トリアゾロ[1,5-a]ピリミジン-7-イルアミン;
5-イソプロピル-6-オクチル-[1,2,4]トリアゾロ[1,5-a]ピリミジン-7-イルアミン;
5-エチル-6-(3,5,5-トリメチルヘキシル)-[1,2,4]トリアゾロ[1,5-a]ピリミジン-7-イルアミン;
5-シクロプロピル-6-オクチル-[1,2,4]トリアゾロ[1,5-a]ピリミジン-7-イルアミン;
5-エチル-6-ペンチル-[1,2,4]トリアゾロ[1,5-a]ピリミジン-7-イルアミン;
5-エチル-6-ヘキシル-[1,2,4]トリアゾロ[1,5-a]ピリミジン-7-イルアミン;
5-エチル-6-ヘプチル-[1,2,4]トリアゾロ[1,5-a]ピリミジン-7-イルアミン;
5-エチル-6-ノニル-[1,2,4]トリアゾロ[1,5-a]ピリミジン-7-イルアミン;
5-エチル-6-ウンデシル-[1,2,4]トリアゾロ[1,5-a]ピリミジン-7-イルアミン;
6-ヘキシル-5-イソプロピル-[1,2,4]トリアゾロ[1,5-a]ピリミジン-7-イルアミン;
6-ヘプチル-5-イソプロピル-[1,2,4]トリアゾロ[1,5-a]ピリミジン-7-イルアミン;
5-イソプロピル-6-ノニル-[1,2,4]トリアゾロ[1,5-a]ピリミジン-7-イルアミン;
5-エチル-6-(3-ペンチルオキシプロピル)-[1,2,4]トリアゾロ[1,5-a]ピリミジン-7-イルアミン。 - 請求項8に記載の式IVまたはVの化合物。
- 固体担体または液体担体と請求項1〜7のいずれか1項に記載の式Iで表される化合物とを含む、抗真菌性組成物。
- 100kg当たり1〜1000gの量で、請求項1〜7のいずれか1項に記載の式Iで表される化合物を含む種子。
- 植物病原性有害真菌類を防除する方法であって、真菌類、または真菌類による病害から保護すべき資材、植物、土壌もしくは種子を、請求項1〜7のいずれか1項に記載の式Iで表される化合物の有効量で処理することを含む、前記方法。
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SI (1) | SI1725561T1 (ja) |
TW (1) | TWI348354B (ja) |
UA (1) | UA81873C2 (ja) |
UY (1) | UY28800A1 (ja) |
WO (1) | WO2005087773A1 (ja) |
ZA (1) | ZA200608384B (ja) |
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