JP3770500B2 - シアノアントラニルアミド殺虫剤 - Google Patents
シアノアントラニルアミド殺虫剤 Download PDFInfo
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- JP3770500B2 JP3770500B2 JP2005148184A JP2005148184A JP3770500B2 JP 3770500 B2 JP3770500 B2 JP 3770500B2 JP 2005148184 A JP2005148184 A JP 2005148184A JP 2005148184 A JP2005148184 A JP 2005148184A JP 3770500 B2 JP3770500 B2 JP 3770500B2
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- 239000002917 insecticide Substances 0.000 title description 7
- YTMXCDUAABXHGB-UHFFFAOYSA-N 2-amino-n-cyanobenzamide Chemical compound NC1=CC=CC=C1C(=O)NC#N YTMXCDUAABXHGB-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 222
- 239000000203 mixture Substances 0.000 claims abstract description 102
- 241000607479 Yersinia pestis Species 0.000 claims abstract description 87
- 238000000034 method Methods 0.000 claims abstract description 65
- 239000007787 solid Substances 0.000 claims abstract description 62
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 30
- 229910052794 bromium Inorganic materials 0.000 claims abstract description 26
- 239000003085 diluting agent Substances 0.000 claims abstract description 21
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 18
- 239000007788 liquid Substances 0.000 claims abstract description 13
- 150000003839 salts Chemical class 0.000 claims abstract description 12
- 150000001204 N-oxides Chemical class 0.000 claims abstract description 11
- 239000004094 surface-active agent Substances 0.000 claims abstract description 11
- 239000007921 spray Substances 0.000 claims description 22
- 241000255925 Diptera Species 0.000 claims description 13
- 239000004480 active ingredient Substances 0.000 claims description 10
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 10
- 241000239290 Araneae Species 0.000 claims description 9
- 241000257303 Hymenoptera Species 0.000 claims description 9
- 241000256856 Vespidae Species 0.000 claims description 9
- 241000238876 Acari Species 0.000 claims description 8
- 239000005667 attractant Substances 0.000 claims description 8
- 241000256602 Isoptera Species 0.000 claims description 6
- 239000003906 humectant Substances 0.000 claims description 6
- 239000003380 propellant Substances 0.000 claims description 6
- 241001674044 Blattodea Species 0.000 claims description 5
- 241000257226 Muscidae Species 0.000 claims description 5
- 230000031902 chemoattractant activity Effects 0.000 claims description 5
- 235000012041 food component Nutrition 0.000 claims description 5
- 239000005417 food ingredient Substances 0.000 claims description 5
- 239000003814 drug Substances 0.000 claims description 3
- 229940079593 drug Drugs 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 abstract description 16
- 229910052739 hydrogen Inorganic materials 0.000 abstract description 9
- 125000001424 substituent group Chemical group 0.000 abstract description 4
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 abstract description 3
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 abstract description 3
- 125000005843 halogen group Chemical group 0.000 abstract description 2
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 abstract 1
- -1 tertiary amine N-oxides Chemical class 0.000 description 98
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 78
- 238000012360 testing method Methods 0.000 description 77
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 76
- 238000006243 chemical reaction Methods 0.000 description 70
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 52
- 239000000047 product Substances 0.000 description 52
- 239000011541 reaction mixture Substances 0.000 description 50
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 45
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 42
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 42
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 42
- 239000000243 solution Substances 0.000 description 42
- 238000002360 preparation method Methods 0.000 description 39
- 239000002904 solvent Substances 0.000 description 36
- 241000196324 Embryophyta Species 0.000 description 35
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 32
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 30
- 239000000460 chlorine Substances 0.000 description 29
- 239000003795 chemical substances by application Substances 0.000 description 25
- 239000000741 silica gel Substances 0.000 description 25
- 229910002027 silica gel Inorganic materials 0.000 description 25
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 25
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 24
- 239000002253 acid Substances 0.000 description 22
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 20
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 18
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 18
- 239000002585 base Substances 0.000 description 18
- 241000238631 Hexapoda Species 0.000 description 16
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 16
- 239000002689 soil Substances 0.000 description 16
- KOPFEFZSAMLEHK-UHFFFAOYSA-N 1h-pyrazole-5-carboxylic acid Chemical compound OC(=O)C=1C=CNN=1 KOPFEFZSAMLEHK-UHFFFAOYSA-N 0.000 description 15
- 241001124076 Aphididae Species 0.000 description 15
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- 150000002367 halogens Chemical class 0.000 description 15
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 14
- 238000009472 formulation Methods 0.000 description 14
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 14
- 241000995027 Empoasca fabae Species 0.000 description 13
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 13
- 238000004587 chromatography analysis Methods 0.000 description 13
- 238000005507 spraying Methods 0.000 description 13
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 12
- 239000012359 Methanesulfonyl chloride Substances 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- NYPJDWWKZLNGGM-UHFFFAOYSA-N fenvalerate Chemical compound C=1C=C(Cl)C=CC=1C(C(C)C)C(=O)OC(C#N)C(C=1)=CC=CC=1OC1=CC=CC=C1 NYPJDWWKZLNGGM-UHFFFAOYSA-N 0.000 description 12
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 12
- HQQTZCPKNZVLFF-UHFFFAOYSA-N 4h-1,2-benzoxazin-3-one Chemical compound C1=CC=C2ONC(=O)CC2=C1 HQQTZCPKNZVLFF-UHFFFAOYSA-N 0.000 description 11
- 241000254173 Coleoptera Species 0.000 description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 11
- 239000003921 oil Substances 0.000 description 11
- 235000019198 oils Nutrition 0.000 description 11
- 238000004809 thin layer chromatography Methods 0.000 description 11
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
- 239000005660 Abamectin Substances 0.000 description 9
- 241000193388 Bacillus thuringiensis Species 0.000 description 9
- 241000258937 Hemiptera Species 0.000 description 9
- 241000244206 Nematoda Species 0.000 description 9
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 9
- 229940097012 bacillus thuringiensis Drugs 0.000 description 9
- 239000012267 brine Substances 0.000 description 9
- 230000006378 damage Effects 0.000 description 9
- 239000008187 granular material Substances 0.000 description 9
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 9
- 235000017557 sodium bicarbonate Nutrition 0.000 description 9
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 9
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 8
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 8
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 8
- 230000000694 effects Effects 0.000 description 8
- 239000000284 extract Substances 0.000 description 8
- 235000013305 food Nutrition 0.000 description 8
- 230000003647 oxidation Effects 0.000 description 8
- 238000007254 oxidation reaction Methods 0.000 description 8
- 238000010992 reflux Methods 0.000 description 8
- 239000004576 sand Substances 0.000 description 8
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 8
- PHXAJGIUKCZJJI-UHFFFAOYSA-N 3-oxo-4h-1,2-benzoxazine-4-carbonitrile Chemical compound C1=CC=C2C(C#N)C(=O)NOC2=C1 PHXAJGIUKCZJJI-UHFFFAOYSA-N 0.000 description 7
- 241000256593 Brachycaudus schwartzi Species 0.000 description 7
- 241000220259 Raphanus Species 0.000 description 7
- DOBRDRYODQBAMW-UHFFFAOYSA-N copper(i) cyanide Chemical compound [Cu+].N#[C-] DOBRDRYODQBAMW-UHFFFAOYSA-N 0.000 description 7
- 238000010168 coupling process Methods 0.000 description 7
- 125000000623 heterocyclic group Chemical group 0.000 description 7
- 238000002156 mixing Methods 0.000 description 7
- 229910052698 phosphorus Inorganic materials 0.000 description 7
- 239000011574 phosphorus Substances 0.000 description 7
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- 238000003786 synthesis reaction Methods 0.000 description 7
- 150000003512 tertiary amines Chemical class 0.000 description 7
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 229910021595 Copper(I) iodide Inorganic materials 0.000 description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- 241000237858 Gastropoda Species 0.000 description 6
- 241001465754 Metazoa Species 0.000 description 6
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 6
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 6
- 244000046052 Phaseolus vulgaris Species 0.000 description 6
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 6
- 150000001298 alcohols Chemical class 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 6
- LSXDOTMGLUJQCM-UHFFFAOYSA-M copper(i) iodide Chemical compound I[Cu] LSXDOTMGLUJQCM-UHFFFAOYSA-M 0.000 description 6
- 238000005859 coupling reaction Methods 0.000 description 6
- 239000012043 crude product Substances 0.000 description 6
- 235000013399 edible fruits Nutrition 0.000 description 6
- ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 6
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 6
- 235000019341 magnesium sulphate Nutrition 0.000 description 6
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 6
- HOKKPVIRMVDYPB-UVTDQMKNSA-N (Z)-thiacloprid Chemical compound C1=NC(Cl)=CC=C1CN1C(=N/C#N)/SCC1 HOKKPVIRMVDYPB-UVTDQMKNSA-N 0.000 description 5
- ZOCSXAVNDGMNBV-UHFFFAOYSA-N 5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-[(trifluoromethyl)sulfinyl]-1H-pyrazole-3-carbonitrile Chemical compound NC1=C(S(=O)C(F)(F)F)C(C#N)=NN1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl ZOCSXAVNDGMNBV-UHFFFAOYSA-N 0.000 description 5
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- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 239000005888 Clothianidin Substances 0.000 description 4
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- 150000003871 sulfonates Chemical class 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
- JXHJNEJVUNHLKO-UHFFFAOYSA-N sulprofos Chemical compound CCCSP(=S)(OCC)OC1=CC=C(SC)C=C1 JXHJNEJVUNHLKO-UHFFFAOYSA-N 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- ZZYSLNWGKKDOML-UHFFFAOYSA-N tebufenpyrad Chemical compound CCC1=NN(C)C(C(=O)NCC=2C=CC(=CC=2)C(C)(C)C)=C1Cl ZZYSLNWGKKDOML-UHFFFAOYSA-N 0.000 description 1
- UBCKGWBNUIFUST-YHYXMXQVSA-N tetrachlorvinphos Chemical compound COP(=O)(OC)O\C(=C/Cl)C1=CC(Cl)=C(Cl)C=C1Cl UBCKGWBNUIFUST-YHYXMXQVSA-N 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
- BSYVTEYKTMYBMK-UHFFFAOYSA-N tetrahydrofurfuryl alcohol Chemical compound OCC1CCCO1 BSYVTEYKTMYBMK-UHFFFAOYSA-N 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- WROMPOXWARCANT-UHFFFAOYSA-N tfa trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F WROMPOXWARCANT-UHFFFAOYSA-N 0.000 description 1
- 239000002562 thickening agent Substances 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
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 239000003053 toxin Substances 0.000 description 1
- 231100000765 toxin Toxicity 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 230000005945 translocation Effects 0.000 description 1
- 238000002054 transplantation Methods 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
- 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
- 239000002383 tung oil Substances 0.000 description 1
- JABYJIQOLGWMQW-UHFFFAOYSA-N undec-4-ene Chemical compound CCCCCCC=CCCC JABYJIQOLGWMQW-UHFFFAOYSA-N 0.000 description 1
- 150000003672 ureas Chemical class 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
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 238000001238 wet grinding Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 239000012138 yeast extract Substances 0.000 description 1
- GTLDTDOJJJZVBW-UHFFFAOYSA-N zinc cyanide Chemical compound [Zn+2].N#[C-].N#[C-] GTLDTDOJJJZVBW-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
- A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
- A01N43/14—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom six-membered rings
- A01N43/16—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom six-membered rings with oxygen as the ring hetero atom
-
- 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
- A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
- A01N43/24—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero 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
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
-
- 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
- A01N43/707—1,2,3- or 1,2,4-triazines; Hydrogenated 1,2,3- or 1,2,4-triazines
-
- 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
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/84—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms six-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,4
-
- 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
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/88—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms six-membered rings with three ring hetero 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
- A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
- A01N57/10—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-oxygen bonds or phosphorus-to-sulfur bonds
- A01N57/14—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-oxygen bonds or phosphorus-to-sulfur bonds containing aromatic radicals
-
- 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
- A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
- A01N57/26—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-nitrogen bonds
- A01N57/28—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-nitrogen bonds containing acyclic or cycloaliphatic radicals
-
- 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
- A01N59/00—Biocides, pest repellants or attractants, or plant growth regulators containing elements or inorganic compounds
- A01N59/02—Sulfur; Selenium; Tellurium; Compounds thereof
-
- 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
- A01N59/00—Biocides, pest repellants or attractants, or plant growth regulators containing elements or inorganic compounds
- A01N59/16—Heavy metals; Compounds thereof
- A01N59/20—Copper
-
- 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
- A01N63/00—Biocides, pest repellants or attractants, or plant growth regulators containing microorganisms, viruses, microbial fungi, animals or substances produced by, or obtained from, microorganisms, viruses, microbial fungi or animals, e.g. enzymes or fermentates
- A01N63/20—Bacteria; Substances produced thereby or obtained therefrom
- A01N63/22—Bacillus
- A01N63/23—B. thuringiensis
-
- 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
- A01N63/00—Biocides, pest repellants or attractants, or plant growth regulators containing microorganisms, viruses, microbial fungi, animals or substances produced by, or obtained from, microorganisms, viruses, microbial fungi or animals, e.g. enzymes or fermentates
- A01N63/30—Microbial fungi; Substances produced thereby or obtained therefrom
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- 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
- A01N63/00—Biocides, pest repellants or attractants, or plant growth regulators containing microorganisms, viruses, microbial fungi, animals or substances produced by, or obtained from, microorganisms, viruses, microbial fungi or animals, e.g. enzymes or fermentates
- A01N63/40—Viruses, e.g. bacteriophages
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- 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
- A01N63/00—Biocides, pest repellants or attractants, or plant growth regulators containing microorganisms, viruses, microbial fungi, animals or substances produced by, or obtained from, microorganisms, viruses, microbial fungi or animals, e.g. enzymes or fermentates
- A01N63/50—Isolated enzymes; Isolated proteins
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
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- Engineering & Computer Science (AREA)
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- Plant Pathology (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Virology (AREA)
- Microbiology (AREA)
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- Inorganic Chemistry (AREA)
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- General Chemical & Material Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Tropical Medicine & Parasitology (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Catching Or Destruction (AREA)
Description
R1はMe、Cl、BrまたはFであり、
R2はF、Cl、Br、C1〜C4ハロアルキルまたはC1〜C4ハロアルコキシであり、
R3はF、ClまたはBrであり、
R4はH;それぞれ場合によりハロゲン、CN、SMe、S(O)Me、S(O)2MeおよびOMeよりなる群から選択される1個の置換基によって置換されていてもよい、C1〜C4アルキル、C3〜C4アルケニル、C3〜C4アルキニル、C3〜C5シクロアルキルまたはC4〜C6シクロアルキルアルキルであり、
R5はHまたはMeであり、
R6はH、FまたはClであり、そして
R7はH、FまたはClである]
の化合物、それらのN−オキシドまたはそれらの塩に関する。
R4は場合によりH、またはCN、SMeおよびOMeよりなる群から選択される1個の置換基によって置換されていてもよいC1〜C4アルキルであり、
R5はHまたはMeであり、
R6はHであり、そして
R7はHである
式Iの化合物である。
好ましい1.R1はMeまたはClであり、
R2はCl、Br、CF3、OCF2H、OCF3またはOCH2CF3であり、そして
R4はH、Me、Et、i−Pr、t−Bu、CH2CN、CH(Me)CH2SMeまたはC(Me)2CH2SMeである
式1の化合物。
R4はH、Me、Etまたはi−Prであり、そして
R5はHである
好ましい1の化合物。
かつR8がC1〜C4アルキルである式22の化合物を調製することができる。
1−(3−クロロ−2−ピリジニル)−N−[4−シアノ−2−メチル−6−(アミノカルボニル)フェニル]−3−(トリフルオロメチル)−1H−ピラゾール−5−カルボキサミドの調製
工程A:2−アミノ−3−メチル−5−ヨード安息香酸の調製
N,N−ジメチルホルムアミド(30mL)中2−アミノ−3−メチル安息香酸(アルドリッチ(Aldrich)、5g、33ミリモル)の溶液に、N−ヨードスクシンイミド(7.8g、34.7ミリモル)を添加し、そして反応混合物を75℃の油浴中で一晩懸濁させた。熱を取り外し、次いで反応混合物をゆっくり氷水(100mL)中へ注ぎ入れ、淡灰色固体を沈殿させた。固体を濾過し、そして4回水で洗浄し、次いで70℃の真空オーブン中に置き、一晩乾燥させた。淡灰色固体として所望の中間体(8.8g)を単離した。
1H NMR(DMSO−d6):δ7.86(d,1H),7.44(d,1H),2.08(s,3H)
乾燥N,N−ジメチルホルムアミド(300mL)中2,3−ジクロロピリジン(99.0g、0.67モル)および3−(トリフルオロメチル)ピラゾール(83g、0.61モル)の混合物に、炭酸カリウム(166.0g、1.2モル)を添加し、次いで48時間かけて反応を110〜125℃まで加熱した。反応を100℃まで冷却し、そしてセライト(Celite)(登録商標)珪藻土フィルターエイドを通して濾過し、固体を除去した。周囲圧力での蒸留によって、N,N−ジメチルホルムアミドおよび過剰量のジクロロピリジンを除去した。減圧下での生成物の蒸留(b.p.139〜141℃、7mm)によって、透明黄色油状物として113.4gの所望の中間体を得た。
1H NMR(CDCl3):δ8.45(d,1H),8.15(s,1H),7.93(d,1H),7.36(t,1H),6.78(s,1H)
−75℃の乾燥テトラヒドロフラン(700mL)中3−クロロ−2−[3−(トリフルオロメチル)−1H−ピラゾール−1−イル]ピリジン(すなわち、工程Bからのピラゾール生成物)(105.0g、425ミリモル)の溶液に、カニューレを通して、乾燥テトラヒドロフラン(300mL)中リチウムジイソプロピルアミド(425ミリモル)の−30℃溶液を添加した。深赤色溶液を15分間撹拌し、その後、溶液が淡黄色になって、そして発熱が停止するまで、−63℃で二酸化炭素をバブリングした。反応をさらに20分間撹拌し、次いで水(20mL)でクエンチングした。溶媒を減圧下で除去し、そして反応混合物を、エーテルと0.5N水酸化ナトリウム水溶液との間で分配した。水性抽出物をエーテル(3×)で洗浄し、セライト(Celite)(登録商標)珪藻土フィルターエイドを通して濾過し、残渣固体を除去し、次いで、オレンジ色油状物が形成する約4のpHまで酸性化した。水性混合物を強力に撹拌し、そして2.5〜3までpHを低下させるために、さらに酸を添加した。オレンジ色油状物は顆粒状固体へと凝固し、これを濾過し、水と1N塩酸とで連続的に洗浄し、そして真空下50℃で乾燥させ、オフホワイト色固体として130gの表題の生成物を得た。類似手順に従うもう1回の実行からの生成物は、175〜176℃で融解した。
1H NMR(DMSO−d6):δ7.61(s,1H),7.76(dd,1H),8.31(d,1H),8.60(d,1H)
−5℃で、アセトニトリル(50mL)中塩化メタンスルホニル(2.91mL、37.74ミリモル)の溶液に、アセトニトリル(50mL)中1−(3−クロロ−2−ピリジニル)−3−(トリフルオロメチル)−1H−ピラゾール−5−カルボン酸(すなわち、工程Cのカルボン酸生成物)(10.0g、34.31ミリモル)およびトリエチルアミン(4.78mL、34.31ミリモル)の混合物を滴下して添加した。次いで、試薬の連続添加の間、反応温度を0℃に維持した。20分間撹拌後、2−アミノ−3−メチル−5−ヨード安息香酸(すなわち、工程Aからの生成物)(9.51g、34.31ミリモル)を添加し、そしてさらに10分間、撹拌を続けた。次いで、アセトニトリル(15mL)中トリエチルアミン(9.56mL、68.62ミリモル)の溶液を滴下して添加し、そして反応混合物を30分間撹拌し、続いて、塩化メタンスルホニル(2.91mL、37.74ミリモル)を添加した。次いで、反応混合物を室温まで加温し、そして2時間撹拌した。溶媒を減圧下でエバポレーションし、そして残渣固体をシリカゲル上クロマトグラフィーによって精製し、黄色固体として8.53gの表題の化合物を得た。
1H NMR(CDCl3):δ8.59(dd,1H),8.35(d,1H),7.97(dd,1H),7.86(d,1H),7.49(m,2H),1.79(s,3H)
室温で、テトラヒドロフラン(10mL)中2−[1−(3−クロロ−2−ピリジニル)−3−(トリフルオロメチル)−1H−ピラゾール−5−イル]−6−ヨード−8−メチル−4H−3,1−ベンゾオキサジン−4−オン(すなわち、工程Dのベンゾオキサジノン生成物)(500mg、0.94ミリモル)の溶液に、ヨウ化銅(I)(180mg、0.094ミリモル)、テトラキス(トリフェニルホスフィン)パラジウム(0)(5.4mg、0.047ミリモル)およびシアン化銅(I)(420mg、4.7ミリモル)を連続的に添加した。還流下で反応混合物を一晩加熱後、追加のシアン化銅(I)(420mg、4.7ミリモル)、ヨウ化銅(I)(107mg、0.56ミリモル)およびテトラキス(トリフェニルホスフィン)パラジウム(0)(325mg、0.28ミリモル)を添加し、そして還流を1時間続けた。反応混合物の色は黒色に変わり、この時点で、シリカゲル薄層クロマトグラフィーによって反応の完了を確認した。次いで、反応混合物を酢酸エチル(20mL)によって希釈し、そしてセライト(Celite)(登録商標)を通して濾過し、続いて、10%重炭酸ナトリウム水溶液によって3回、そしてブラインによって1回洗浄した。有機抽出物を乾燥させ(MgSO4)、そして減圧下で濃縮し、粗製黄色固体として410mgの表題の化合物を得た。
1H NMR(CDCl3):δ8.59(dd,1H),8.33(d,1H),8.03(dd,1H),7.95(d,1H),7.56(m,2H),1.88(s,3H)
室温で、テトラヒドロフラン(5mL)中2−[1−(3−クロロ−2−ピリジニル)−3−(トリフルオロメチル)−1H−ピラゾール−5−イル]−6−シアノ−8−メチル−4H−3,1−ベンゾオキサジン−4−オン(すなわち、工程Eのシアノベンゾオキサジノン生成物)(200mg、0.46ミリモル)の溶液に、水酸化アンモニウム(0.5mL、12.8ミリモル)を滴下して添加した。次いで、反応混合物を5分間撹拌し、この時点で、シリカゲル薄層クロマトグラフィーによって反応の完了を確認した。テトラヒドロフラン溶媒を減圧下でエバポレーションし、そして残渣固体をシリカゲル上クロマトグラフィーによって精製し、200℃〜202℃で融解する固体として本発明の化合物である表題の化合物620mgを得た。
1H NMR(CDCl3):δ10.65(s,1H),8.43(dd,1H),7.9(dd,1H),7.67(s,1H),7.63(s,1H),7.45(m,1H),7.25(s,1H),6.21(bs,1H),5.75(bs,1H),2.26(s,3H)
1−(3−クロロ−2−ピリジニル)−N−[4−シアノ−2−メチル−6−[(メチルアミノ)カルボニル]フェニル]−3−(トリフルオロメチル)−1H−ピラゾール−5−カルボキサミドの調製
工程A:1−(3−クロロ−2−ピリジニル)−N−[4−ヨード−2−メチル−6−[(メチルアミノ)カルボニル]フェニル]−3−(トリフルオロメチル)−1H−ピラゾール−5−カルボキサミドの調製
テトラヒドロフラン(15mL)中2−[1−(3−クロロ−2−ピリジニル)−3−(トリフルオロメチル)−1H−ピラゾール−5−イル]−6−ヨード−8−メチル−4H−3,1−ベンゾオキサジン−4−オン(すなわち、実施例1、工程Dのベンゾオキサジノン生成物)(500mg、0.94ミリモル)の溶液に、メチルアミン(THF中2.0M溶液、1.4mL、2.8ミリモル)を滴下して添加し、そして反応混合物を3時間撹拌し、この時点で、シリカゲル薄層クロマトグラフィーによって反応の完了を確認した。テトラヒドロフラン溶媒を減圧下でエバポレーションし、そして残渣固体をシリカゲル上クロマトグラフィーによって精製し、黄色固体として400mgの表題の化合物を得た。
1H NMR(CDCl3):δ10.25(s,1H),8.45(dd,1H),7.85(dd,1H),7.55(s,1H),7.50(s,1H),7.46(s,1H),7.40(m,1H),6.15(d,1H),2.93(d,3H),2.12(s,3H)
室温で、テトラヒドロフラン(8mL)中1−(3−クロロ−2−ピリジニル)−N−[4−ヨード−2−メチル−6−[(メチルアミノ)カルボニル]フェニル]−3−(トリフルオロメチル)−1H−ピラゾール−5−カルボキサミド(すなわち、工程Aのジアミド生成物)(410mg、0.72ミリモル)の溶液に、ヨウ化銅(I)(24mg、0.126ミリモル)、テトラキス(トリフェニルホスフィン)パラジウム(0)(70mg、0.060ミリモル)およびシアン化銅(I)(640mg、7.2ミリモル)を連続的に添加した。還流下で反応混合物を4.5時間加熱した。シリカゲル薄層クロマトグラフィーによって反応の完了を確認した。次いで、反応混合物を酢酸エチル(20mL)によって希釈し、そしてセライト(Celite)(登録商標)を通して濾過し、続いて、10%重炭酸ナトリウム水溶液によって3回、そしてブラインによって1回洗浄した。有機抽出物を乾燥させ(MgSO4)、そして減圧下で濃縮し、そして残渣固体をシリカゲル上クロマトグラフィーによって精製し、214℃〜216℃で融解する白色固体として、本発明の化合物である表題の化合物114mgを得た。
1H NMR(CDCl3):δ10.70(s,1H),8.46(dd,1H),7.87(dd,1H),7.57(s,2H),7.45(m,1H),7.31(s,1H),6.35(d,1H),2.98(d,3H),2.24(s,3H)
3−クロロ−1−(3−クロロ−2−ピリジニル)−N−[4−シアノ−2−メチル−6−[(メチルアミノ)カルボニル]フェニル]−1H−ピラゾール−5−カルボキサミドの調製
工程A:3−クロロ−N,N−ジメチル−1H−ピラゾール−1−スルホンアミドの調製
−78℃の乾燥テトラヒドロフラン(1500mL)中N−ジメチルスルファモイルピラゾール(188.0g、1.07モル)の溶液に、温度を−65℃未満に保持しながら、ヘキサン中2.5Mのn−ブチルリチウムの溶液(472mL、1.18モル)を滴下して添加した。添加完了時に、反応混合物をさらに45分間、−78℃に維持し、その後、テトラヒドロフラン(120mL)中ヘキサクロロエタン(279g、1.18モル)の溶液を滴下して添加した。反応混合物を1時間、−78℃に維持し、−20℃まで加温し、次いで、水(1L)でクエンチングした。反応混合物を塩化メチレン(4×500mL)で抽出し、そして有機抽出物を硫酸マグネシウム上で乾燥させ、そして濃縮した。溶出剤として塩化メチレンを使用して、シリカゲル上クロマトグラフィーによって粗製生成物をさらに精製し、黄色油状物として160gの表題の生成化合物を得た。
1H NMR(CDCl3):δ7.61(s,1H),6.33(s,1H),3.07(d,6H)
トリフルオロ酢酸(290mL)に、3−クロロ−N,N−ジメチル−1H−ピラゾール−1−スルホンアミド(すなわち、工程Aのクロロピラゾール生成物)(160g)を滴下して添加し、そして反応混合物を室温で1.5時間撹拌し、次いで、減圧下で濃縮した。残渣をヘキサンに溶解し、不溶性固体を濾過し、そしてヘキサンを濃縮して、油状物として粗製生成物を得た。溶出剤としてエーテル/ヘキサン(40:60)を使用して、シリカゲル上クロマトグラフィーによって粗製生成物をさらに精製し、黄色油状物として64.44gの表題の生成物を得た。
1H NMR(CDCl3):δ6.39(s,1H),7.66(s,1H),9.6(br s,1H)
N,N−ジメチルホルムアミド(400mL)中2,3−ジクロロピリジン(92.60g、0.629モル)および3−クロロピラゾール(すなわち、工程Bの生成物)(64.44g、0.629モル)の混合物に、炭酸カリウム(147.78g、1.06モル)を添加し、次いで、反応混合物を36時間、100℃まで加熱した。反応混合物を室温まで冷却し、そしてゆっくり氷水中に注ぎ入れた。沈殿した固形物を濾過し、そして水で洗浄した。固体濾過ケーキを酢酸エチルに溶解し、硫酸マグネシウム上で乾燥させ、そして濃縮した。溶出剤として20%酢酸エチル/ヘキサンを使用して、粗製固体をシリカゲル上クロマトグラフし、白色固体として39.75gの表題の生成物を得た。
1H NMR(CDCl3):δ6.43(s,1H),7.26(m,1H),7.90(d,1H),8.09(s,1H),8.41(d,1H)
−78℃の乾燥テトラヒドロフラン(400mL)中3−クロロ−2−(3−クロロ−1H−ピラゾール−1−イル)ピリジン(すなわち、工程Cのピラゾール生成物)(39.75g、186ミリモル)の溶液に、テトラヒドロフラン中2.0Mのリチウムジイソプロピルアミド(93mL、186ミリモル)の溶液を滴下して添加した。二酸化炭素を14分間、琥珀色溶液を通してバブリングし、その後、溶液は、淡い茶色がかった黄色になった。1N水酸化ナトリウム水溶液によって反応を塩基性にさせ、そしてエーテル(2×500mL)で抽出した。水性抽出物を6N塩酸で酸性化し、続いて、酢酸エチル(3×500mL)で抽出した。酢酸エチル抽出物を硫酸マグネシウム上で乾燥させ、そして濃縮し、オフホワイト色固体として42.96gの表題の生成物を得た。同一手順に従うもう1回の実行からの生成物は、198〜199℃で融解した。
1H NMR(DMSO−d6):δ6.99(s,1H),7.45(m,1H),7.93(d,1H),8.51(d,1H)
0℃で、アセトニトリル(10mL)中塩化メタンスルホニル(0.63mL、8.13ミリモル)の溶液に、アセトニトリル(5mL)中3−クロロ−1−(3−クロロ−2−ピリジニル)−1H−ピラゾール−5−カルボン酸(すなわち、工程Dのカルボン酸生成物)(2.0g、7.75ミリモル)およびトリエチルアミン(1.08mL、7.75ミリモル)の混合物を滴下して添加した。次いで、反応混合物を0℃で15分間撹拌した。次いで、2−アミノ−3−メチル−5−ヨード安息香酸(すなわち、実施例1、工程Aからの生成物)(2.14g、7.75ミリモル)を添加し、そしてさらに5分間、撹拌を続けた。次いで、5℃未満の温度を保持しながら、アセトニトリル(5mL)中トリエチルアミン(2.17mL、15.15ミリモル)の溶液を滴下して添加した。反応混合物を0℃で40分間撹拌し、次いで、塩化メタンスルホニル(0.63mL、8.13ミリモル)を添加した。次いで、反応混合物を室温まで加温し、そして一晩撹拌した。次いで、反応混合物を水(50mL)で希釈し、そして酢酸エチル(3×50mL)で抽出した。組み合わせた酢酸エチル抽出物を、10%重炭酸ナトリウム水溶液(1×20mL)、そしてブライン(1×20mL)で連続的に洗浄し、乾燥させ(MgSO4)、そして濃縮し、粗製黄色固体として3.18gの表題の生成物を得た。
1H NMR(CDCl3):δ8.55(dd,1H),8.33(s,1H),7.95(dd,1H),7.82(d,1H),7.45(m,1H),7.16(s,1H),1.77(s,3H)
室温で、テトラヒドロフラン(15mL)中2−[3−クロロ−1−(3−クロロ−2−ピリジニル)−1H−ピラゾール−5−イル]−6−ヨード−8−メチル−4H−3,1−ベンゾオキサジン−4−オン(すなわち、工程Eのベンゾオキサジノン生成物)(600mg、1.2ミリモル)の溶液に、ヨウ化銅(I)(137mg、0.72ミリモル)、テトラキス(トリフェニルホスフィン)パラジウム(0)(416mg、0.36ミリモル)およびシアン化銅(I)(860mg、9.6ミリモル)を連続的に添加した。次いで、還流下で反応混合物を一晩加熱した。反応の色は黒色に変わり、この時点で、シリカゲル薄層クロマトグラフィーによって反応の完了を確認した。反応を酢酸エチル(20mL)によって希釈し、そしてセライト(Celite)(登録商標)を通して濾過し、続いて、10%重炭酸ナトリウム水溶液によって3回、そしてブラインによって1回洗浄した。有機抽出物を乾燥させ(MgSO4)、そして減圧下で濃縮し、粗製黄色固体として397mgの表題の化合物を得た。
1H NMR(CDCl3):δ8.50(q,1H),8.22(d,1H),7.90(dd,1H),7.67(d,1H),7.45(m,1H),7.15(s,1H),1.79(s,3H)
テトラヒドロフラン(5mL)中2−[3−クロロ−1−(3−クロロ−2−ピリジニル)−1H−ピラゾール−5−イル]−6−シアノ−8−メチル−4H−3,1−ベンゾオキサジン−4−オン(例えば、工程Fのシアノベンゾオキサジノン生成物)(100mg、0.25ミリモル)の溶液に、メチルアミン(THF中2.0M溶液、0.5mL、1.0ミリモル)を滴下して添加し、そして反応混合物を5分間撹拌し、この時点で、シリカゲル薄層クロマトグラフィーによって反応の完了を確認した。テトラヒドロフラン溶媒を減圧下でエバポレーションし、そして残渣固体をシリカゲル上クロマトグラフィーによって精製し、白色固体として本発明の化合物である表題の化合物(52mg)を得た。これは、140℃超で融解装置において分解した。
1H NMR(CDCl3):δ10.55(s,1H),8.45(dd,1H),7.85(dd,1H),7.55(d,2H),7.40(m,1H),6.97(d,1H),6.30(d,1H),2.98(d,3H),2.24(d,3H)
3−クロロ−1−(3−クロロ−2−ピリジニル)−N−[4−シアノ−2−メチル−6−(アミノカルボニル)フェニル]−1H−ピラゾール−5−カルボキサミドの調製
室温で、テトラヒドロフラン(5mL)中2−[3−クロロ−1−(3−クロロ−2−ピリジニル)−1H−ピラゾール−5−イル]−6−シアノ−8−メチル−4H−3,1−ベンゾオキサジン−4−オン(すなわち、実施例3、工程Fのシアノベンゾオキサジノン生成物)(100mg、0.25ミリモル)の溶液に、水酸化アンモニウム(0.5mL、12.8ミリモル)を滴下して添加した。次いで、反応混合物を5分間撹拌し、この時点で、シリカゲル薄層クロマトグラフィーによって反応の完了を確認した。テトラヒドロフラン溶媒を減圧下でエバポレーションし、そして残渣固体をシリカゲル上クロマトグラフィーによって精製し、白色固体として本発明の化合物である表題の化合物55mgを得た。これは、255℃超で融解装置において分解した。
1H NMR(CDCl3):δ10.50(s,1H),8.45(dd,1H),7.85(dd,1H),7.66(d,1H),7.61(s,1H),7.41(m,1H),6.95(s,1H),6.25(bs,1H),5.75(bs,1H),2.52(s,3H)
3−ブロモ−1−(3−クロロ−2−ピリジニル)−N−[4−シアノ−2−メチル−6−[(メチルアミノ)カルボニル]フェニル]−1H−ピラゾール−5−カルボキサミドの調製
工程A:3−ブロモ−N,N−ジメチル−1H−ピラゾール−1−スルホンアミドの調製
−78℃の乾燥テトラヒドロフラン(500mL)中N,N−ジメチルスルファモイルピラゾール(44.0g、0.251モル)の溶液に、−60℃未満の温度を維持しながら、n−ブチルリチウム溶液(ヘキサン中2.5M、105.5mL、0.264モル)を滴下して添加した。添加の間、厚みのある固体が形成した。添加完了時、反応混合物をさらに15分間維持し、その後、−70℃未満の温度を維持しながら、テトラヒドロフラン(150mL)中1,2−ジブロモテトラクロロエタン(90g、0.276モル)の溶液を滴下して添加した。反応混合物は透明オレンジ色に変化し、撹拌をさらに15分間続けた。−78℃の浴を取り外し、そして反応を水(600mL)でクエンチングした。反応混合物を塩化メチレン(4×)で抽出し、そして有機抽出物を硫酸マグネシウム上で乾燥させ、そして濃縮した。溶出剤として塩化メチレン−ヘキサン(50:50)を使用するシリカゲル上でのクロマトグラフィーによって、粗製生成物をさらに精製し、透明無色油状物として57.04gの表題の生成物を得た。
1H NMR(CDCl3):δ3.07(d,6H),6.44(m,1H),7.62(m,1H)
トリフルオロ酢酸(70mL)に、3−ブロモ−N,N−ジメチル−1H−ピラゾール−1−スルホンアミド(すなわち、工程Aのブロモピラゾール生成物)(57.04g)をゆっくり添加した。反応混合物を30分間、室温で撹拌し、次いで減圧下で濃縮した。残渣をヘキサン中に溶解し、不溶性固体を濾過して除去し、そしてヘキサンをエバポレーションして、油状物として粗製生成物を得た。溶出剤として酢酸エチル/ジクロロメタン(10:90)を使用して、シリカゲル上クロマトグラフィによって粗製生成物をさらに精製し、油状物を得た。油状物をジクロロメタン中に溶解し、重炭酸ナトリウム水溶液で中和し、塩化メチレン(3×)で抽出し、硫酸マグネシウム上で乾燥させて、そして濃縮し、白色固体として25.9gの表題の生成物を得た。m.p.61〜64℃。
1H NMR(CDCl3):δ6.37(d,1H),7.59(d,1H),12.4(br s,1H)
乾燥N,N−ジメチルホルムアミド(88mL)中2,3−ジクロロピリジン(27.4g、185ミリモル)および3−ブロモピラゾール(すなわち、工程Bの生成物)(25.4g、176ミリモル)の混合物に、炭酸カリウム(48.6g、352ミリモル)を添加し、そして反応混合物を18時間、125℃まで加熱した。反応混合物を室温まで冷却し、そして氷水(800mL)中に注入した。沈殿が形成した。沈殿した固体を1.5時間撹拌し、濾過し、そして水(2×100mL)で洗浄した。固体濾過ケーキを塩化メチレン中に溶解し、そして連続的に水、1N塩酸、飽和重炭酸ナトリウム水溶液およびブラインで洗浄した。次いで、有機抽出物を硫酸マグネシウム上で乾燥させ、そして濃縮し、39.9gのピンク色固体を得た。粗製固体をヘキサン中に懸濁させて、そして1時間強力に撹拌した。固体を濾過し、ヘキサンで洗浄し、そして乾燥させて、オフホワイト色粉末として表題の生成物(30.4g)を得た。これは、NMRによって、純度>94%であると決定された。さらなる精製をせずに、この材料を工程Dで使用した。
1H NMR(CDCl3):δ6.52(s,1H),7.30(dd,1H),7.92(d,1H),8.05(s,1H),8.43(d,1H)
−76℃の乾燥テトラヒドロフラン(250mL)中2−(3−ブロモ−1H−ピラゾール−1−イル)−3−クロロピリジン(すなわち、工程Cのピラゾール生成物)(30.4g、118ミリモル)の溶液に、−71℃未満の温度が保持されるような速度で、テトラヒドロフラン中リチウムジイソプロピルアミド(118ミリモル)の溶液を滴下して添加した。反応混合物を−76℃で15分間撹拌し、次いで、二酸化炭素を10分間バブリングすると、−57℃まで加温が生じた。反応混合物を−20℃まで加温し、そして水でクエンチングした。反応混合物を濃縮し、次いで水(1L)およびエーテル(500mL)中に溶解し、次いで水酸化ナトリウム水溶液(1N、20mL)を添加した。水性抽出物をエーテルで洗浄し、そして塩酸で酸性化した。沈殿した固体を濾過し、水で洗浄し、そして乾燥して、黄褐色固体として27.7gの表題の生成物を得た。類似手順に従うもう1回の実行からの生成物は、200〜201℃で融解した。
1H NMR(DMSO−d6):δ7.25(s,1H),7.68(dd,1H),8.24(d,1H),8.56(d,1H)
0℃で、アセトニトリル(15mL)中塩化メタンスルホニル(0.54mL、6.94ミリモル)の溶液に、アセトニトリル(5mL)中3−ブロモ−1−(3−クロロ−2−ピリジニル)−1H−ピラゾール−5−カルボン酸(すなわち、工程Dのカルボン酸生成物)(2.0g、6.6ミリモル)およびトリエチルアミン(0.92mL、6.6ミリモル)の混合物を滴下して添加した。次いで、反応混合物を0℃で15分間撹拌した。次いで、2−アミノ−3−メチル−5−ヨード安息香酸(すなわち、実施例1、工程Aからの生成物)(1.8g、6.6ミリモル)を添加し、そしてさらに5分間、撹拌を続けた。次いで、5℃未満の温度を保持しながら、アセトニトリル(5mL)中トリエチルアミン(1.85mL、13.2ミリモル)の溶液を滴下して添加した。反応混合物を0℃で40分間撹拌し、次いで、塩化メタンスルホニル(0.54mL、6.94ミリモル)を添加した。次いで、反応混合物を室温まで加温し、そして一晩撹拌した。次いで、反応混合物を水(50mL)で希釈し、そして酢酸エチル(3×50mL)で抽出した。組み合わせた酢酸エチル抽出物を、10%重炭酸ナトリウム水溶液(1×20mL)、そしてブライン(1×20mL)で連続的に洗浄し、乾燥させ(MgSO4)、そして濃縮し、粗製黄色固体として2.24gの表題の生成物を得た。
1H NMR(CDCl3):δ8.55(dd,1H),8.33(d,1H),7.95(dd,1H),7.85(s,1H),7.45(m,1H),7.25(s,1H),1.77(s,3H)
室温で、テトラヒドロフラン(15mL)中2−[3−ブロモ−1−(3−クロロ−2−ピリジニル)−1H−ピラゾール−5−イル]−6−ヨード−8−メチル−4H−3,1−ベンゾオキサジン−4−オン(すなわち、工程Eのベンゾオキサジノン生成物)(600mg、1.1ミリモル)の溶液に、ヨウ化銅(I)(126mg、0.66ミリモル)、テトラキス(トリフェニルホスフィン)パラジウム(0)(382mg、0.33ミリモル)およびシアン化銅(I)(800mg、8.8ミリモル)を連続的に添加した。次いで、還流下で反応混合物を一晩加熱した。反応の色は黒色に変わり、この時点で、シリカゲル薄層クロマトグラフィーによって反応の完了を確認した。反応混合物を酢酸エチル(20mL)によって希釈し、そしてセライト(Celite)(登録商標)を通して濾過し、続いて、10%重炭酸ナトリウム水溶液によって3回、そしてブラインによって1回洗浄した。有機抽出物を乾燥させ(MgSO4)、そして減圧下で濃縮し、粗製黄色固体として440mgの表題の化合物を得た。
1H NMR(CDCl3):δ8.55(m,1H),8.31(d,1H),7.96(dd,1H),7.73(s,1H),7.51(m,1H),7.31(s,1H),1.86(s,3H)
テトラヒドロフラン(5mL)中2−[3−ブロモ−1−(3−クロロ−2−ピリジニル)−1H−ピラゾール−5−イル]−6−シアノ−8−メチル−4H−3,1−ベンゾオキサジン−4−オン(すなわち、工程Fのシアノベンゾオキサジノン生成物)(100mg、0.22ミリモル)の溶液に、メチルアミン(THF中2.0M溶液、0.5mL、1.0ミリモル)を滴下して添加し、そして反応混合物を5分間撹拌し、この時点で、シリカゲル薄層クロマトグラフィーによって反応の完了を確認した。テトラヒドロフラン溶媒を減圧下でエバポレーションし、そして残渣固体をシリカゲル上クロマトグラフィーによって精製し、白色固体として本発明の化合物である表題の化合物(41mg)を得た。これは、180℃超で融解装置において分解した。
1H NMR(CDCl3):δ10.55(s,1H),8.45(dd,1H),7.85(dd,1H),7.57(s,2H),7.37(m,1H),7.05(s,1H),6.30(d,1H),2.98(d,3H),2.24(s,3H)
3−ブロモ−1−(3−クロロ−2−ピリジニル)−N−[4−シアノ−2−メチル−6−(アミノカルボニル)フェニル]−1H−ピラゾール−5−カルボキサミドの調製
室温で、テトラヒドロフラン(5mL)中2−[3−ブロモ−1−(3−クロロ−2−ピリジニル)−1H−ピラゾール−5−イル]−6−シアノ−8−メチル−4H−3,1−ベンゾオキサジン−4−オン(すなわち、実施例5、工程Fのシアノベンゾオキサジノン生成物)(100mg、0.22ミリモル)の溶液に、水酸化アンモニウム(0.5mL、12.8ミリモル)を滴下して添加した。次いで、反応混合物を5分間撹拌し、この時点で、シリカゲル薄層クロマトグラフィーによって反応の完了を確認した。テトラヒドロフラン溶媒を減圧下でエバポレーションし、そして残渣固体をシリカゲル上クロマトグラフィーによって精製し、255℃超の融点を有する白色固体として本発明の化合物である表題の化合物(36mg)を得た。
1H NMR(CDCl3):δ10.52(s,1H),8.45(dd,1H),7.85(dd,1H),7.65(s,1H),7.60(s,1H),7.40(m,1H),7.05(s,1H),6.20(bs,1H),5.75(bs,1H),2.25(s,3H)
3−クロロ−1−(3−クロロ−2−ピリジニル)−N−[2−クロロ−4−シアノ−6−[(メチルアミノ)カルボニル]フェニル]−1H−ピラゾール−5−カルボキサミドの調製
工程A:2−アミノ−3−クロロ−5−ヨード安息香酸の調製
N,N−ジメチルホルムアミド(30mL)中2−アミノ−3−クロロ安息香酸(アルドリッチ(Aldrich)、5g、29.1ミリモル)の溶液に、N−ヨードスクシンイミド(5.8g、26ミリモル)を添加し、そして反応混合物を60℃で一晩加熱した。熱を取り外し、次いで反応混合物をゆっくり氷水(100mL)中へ注ぎ入れ、淡茶色固体を沈殿させた。固体を濾過し、そして4回水で洗浄し、次いで70℃の真空オーブン中に置き、一晩乾燥させた。淡茶色固体として所望の中間体(7.2g)を単離した。
1H NMR(DMSO−d6):δ7.96(d,1H),7.76(t,1H)
0℃で、アセトニトリル(10mL)中塩化メタンスルホニル(0.31mL、4.07ミリモル)の溶液に、アセトニトリル(5mL)中3−クロロ−1−(3−クロロ−2−ピリジニル)−1H−ピラゾール−5−カルボン酸(すなわち、実施例3、工程Dのカルボン酸生成物)(1.0g、3.87ミリモル)およびトリエチルアミン(0.54m
L、3.87ミリモル)の混合物を滴下して添加した。次いで、反応混合物を0℃で15分間撹拌した。次いで、2−アミノ−3−クロロ−5−ヨード安息香酸(すなわち、工程Aからの生成物)(1.15g、3.87ミリモル)を添加し、そしてさらに5分間、撹拌を続けた。次いで、5℃未満の温度を保持しながら、アセトニトリル(5mL)中トリエチルアミン(1.08mL、7.74ミリモル)の溶液を滴下して添加した。反応混合物を0℃で40分間撹拌し、次いで、塩化メタンスルホニル(0.31mL、4.07ミリモル)を添加した。次いで、反応混合物を室温まで加温し、そして一晩撹拌した。次いで、反応混合物を水(50mL)で希釈し、そして酢酸エチル(3×50mL)で抽出した。組み合わせた酢酸エチル抽出物を、10%重炭酸ナトリウム水溶液(1×20mL)、そしてブライン(1×20mL)で連続的に洗浄し、乾燥させ(MgSO4)、そして減圧下で濃縮した。残渣固体をシリカゲル上クロマトグラフィーによって精製し、粗製黄色固体として575mgの表題の生成物を得た。
1H NMR(CDCl3):δ8.55(q,1H),8.39(d,1H),8.04(d,1H),7.94(dd,1H),7.45(m,1H),7.19(s,1H)
室温で、テトラヒドロフラン(15mL)中8−クロロ−2−[3−クロロ−1−(3−クロロ−2−ピリジニル)−1H−ピラゾール−5−イル]−6−ヨード−4H−3,1−ベンゾオキサジン−4−オン(すなわち、工程Bのベンゾオキサジノン生成物)(575mg、1.1ミリモル)の溶液に、ヨウ化銅(I)(840mg、0.44ミリモル)、テトラキス(トリフェニルホスフィン)パラジウム(0)(255mg、0.22ミリモル)およびシアン化銅(I)(500mg、5.5ミリモル)を連続的に添加した。次いで、還流下で反応混合物を一晩加熱した。反応の色は黒色に変わり、この時点で、シリカゲル薄層クロマトグラフィーによって反応の完了を確認した。反応を酢酸エチル(20mL)によって希釈し、そしてセライト(Celite)(登録商標)を通して濾過し、続いて、10%重炭酸ナトリウム水溶液によって3回、そしてブラインによって1回洗浄した。有機抽出物を乾燥させ(MgSO4)、そして減圧下で濃縮し、粗製黄色固体として375mgの表題の化合物を得た。
1H NMR(CDCl3):δ8.55(q,1H),8.36(d,1H),7.95(m,2H),7.5(m,1H)
テトラヒドロフラン(5mL)中8−クロロ−2−[3−クロロ−1−(3−クロロ−2−ピリジニル)−1H−ピラゾール−5−イル]−6−シアノ−4H−3,1−ベンゾオキサジン−4−オン(すなわち、工程Cのシアノベンゾオキサジノン生成物)(187mg、0.446ミリモル)の溶液に、メチルアミン(THF中2.0M溶液、0.5mL、1.0ミリモル)を滴下して添加し、そして反応混合物を5分間撹拌し、この時点で、シリカゲル薄層クロマトグラフィーによって反応の完了を確認した。テトラヒドロフラン溶媒を減圧下でエバポレーションし、そして残渣固体をシリカゲル上クロマトグラフィーによって精製し、197℃〜200℃で融解する白色固体として本発明の化合物である49mgの表題の化合物を得た。
1H NMR(CDCl3):δ10.05(bs,1H),8.45(q,1H),7.85(dd,1H),7.70(d,1H),7.59(d,1H),7.38(m,1H),7.02(s,1H),6.35(d,1H),2.94(d,3H)
本発明の化合物は一般的に、少なくとも1種の液体希釈剤、固体希釈剤または界面活性剤を含んでなる農業的または非農業的使用に適切な担体とともに製剤または組成物として使用される。製剤または組成物成分は、活性成分の物性、適用形態、ならびに土壌タイプ、湿度および温度のような環境要因と調和するように選択される。有用な製剤は、場合によりゲルへと濃厚化されることが可能な、溶液(乳化可能な濃縮物を含む)、懸濁液、乳液(ミクロエマルジョンおよび/またはサスポエマルジョンを含む)等のような液体を含む。有用な製剤はさらに、水分散性(「水和」)または水溶性であり得る、ダスト、粉末、顆粒、ペレット、タブレット、フィルム等のような固体を含む。活性成分を(マイクロ)カプセル化することができ、さらに懸濁液または固体製剤へと形成することができ、あるいは活性成分の全製剤をカプセル化(または「オーバーコート」)することができる。カプセル化により、活性成分放出を制御することができるか、または遅らせることができる。噴霧可能な製剤を適切な培地に施すことができ、1ヘクタールあたり約1〜数百リットルの噴霧量で使用することができる。さらなる製剤の中間体として、最初に高強度組成物を使用する。
イス アクティブ エージェンツ(Encyclopedia of Surface Active Agents)、ケミカル パブリッシング カンパニー インコーポレイテッド(Chemical Publ.Co.,Inc.)、ニューヨーク(New York)、1964は界面活性剤および推奨される使用を記載している。全ての製剤は、発泡、ケーキング、腐食、微生物の増殖等を低下させるための添加剤、または粘度を増加させるための増粘剤を少量含量することが可能である。
スミス(Smith))、シロイチモジヨトウ(Spodoptera exigua ヒュブネル(Huebner))、タマナヤガ(Agrotis ipsilon ハフナゲル(Hufnagel))、イラクサギンウワバ(Trichoplusia ni ヒュブネル(Huebner))、オオタバコガ(Heliothis virescens ファブリシウス(Fabricius))など);メイガ科の穿孔性害虫、繭を作る害虫、食葉に巣を作る群局性害虫、コーンワーム、アオムシ、葉脈を残して葉を食害する害虫(アワノメイガ(Ostrinia nubilalis ヒュブネル(Huebner))、ネーブルオレンジワーム(Amyelois transitella ウォーカー(Walker))、ウスギンツトガ(Crambus caliginosellus クレメンス(Clemens))、クロオビクロノメイガ(Herpetogramma licarsisalis ウォーカー(Walker))など);ハマキガ科のハマキムシ、芽を食害する害虫、種子を食害する害虫、果実を食害する害虫(コドリンガ(Cydia pomonella リンネ(Linnaeus))、グレープベリーモス(Endopiza viteana クレメンス(Clemens))、ナシヒメシンクイ(Grapholitamolesta ブスク(Busck))など);経済的観点から重要な他の多くの鱗翅目(コナガ(Plutella xylostella リンネ(Linnaeus))、ワタアカミムシ(Pectinophora gossypiella ソーンダズ(Saunders))、マイマイガ(Lymantria dispar) リンネ(Linnaeus)など)などの鱗翅目の幼虫;チャバネゴキブリ科およびゴキブリ科(トウヨウゴキブリ(Blatta orientalis リンネ(Linnaeus))、アジアゴキブリ(Blatella asahinai ミズクボ(Mizukubo))、チャバネゴキブリ(Blattella germanica リンネ(Linnaeus))、チャオビゴキブリ(Supella longipalpa ファブリシウス(Fabricius))、ワモンゴキブリ(Periplaneta americana リンネ(Linnaeus))、トビイロゴキブリ(Periplaneta brunnea バーマイスター(Burmeister))、マデラゴキブリ(Leucophaea maderae ファブリシウス(Fabricius)))などのゴキブリをはじめとするゴキブリ目のニンフおよび成虫;ヒゲナガゾウムシ科、マメゾウムシ科、ゾウムシ科のゾウムシ(ワタミゾウムシ(Anthonomus grandis ボヘマン(Boheman))、イネミズゾウムシ(Lissorhoptrus oryzophilus クッシェル(Kuschel))、オサゾウムシ(Sitophilus granarius リンネ(Linnaeus))、ココクゾウムシ(Sitophilus oryzae) リンネ(Linnaeus));ハムシ科のノミハムシ、ウリハムシ、根食い線虫、ハムシ、イモハムシおよびハモグリムシ(コロラドハムシ(Leptinotarsa decemlineata セイ(Say))、ウェスタンコーンルートワーム(Diabrotica virgifera ルコンテ(LeConte))など);コガネムシ科(Scaribaeidae)のコガネムシおよび他の甲虫(マメコガネ(Popillia japonica ニューマン(Newman))、ヨーロピアンコガネムシ(European chafer)(Rhizotrogus majalis ラゾウモブスキー(Razoumowsky))など);カツオブシムシ科のカツオブシムシ;コメツキムシ科のコメツキムシ;キクイムシ科のキクイムシ、ゴミムシダマシ科のコクヌストモドキをはじめとする鞘翅目の食葉性幼虫および成虫が挙げられる。また、農業的および非農業的有害生物にはクギヌキハサミムシ科のハサミムシ(ヨーロッパクギヌキハサミムシ(Forficula auricularia) リンネ(Linnaeus)、ブラックイヤウィグ(black earwig)(Chelisoches morio ファブリシウス(Fabricius))など)をはじめとする革翅目の成虫および幼虫;カスミカメムシ科のカスミカメムシ、セミ科のセミ、ヨコバイ科のヨコバイ(カキノヒメヨコバイ(Empoasca)spp.など)、アワフキムシ科(Fulgoroidae)およびウンカ科のプラントホッパー、ツノゼミ科のツノゼミ、キジラミ科のキジラミ、コナジラミ科のコナジラミ、アブラムシ科のアブラムシ、ネアブラムシ科のネアブラムシ、コナカイガラムシ科のコナカイガラムシ、カタカイガラムシ科、マルカイガラムシ科およびワタフキカイガラムシ科のカイガラムシ、グンバイムシ科のグンバイムシ、カメムシ科のカメムシ、ナガカメムシ科のナガカメムシ(cinch bug)(Blissus spp.など)ならびに他のコバネナガカメムシ、コガシラアワフキ科のアワフキムシ、ヘリカメムシ科のヘリカメムシ、ホシカメムシ科のアカホシカメムシおよびホシカメムシなどの半翅目および同翅目の成虫およびニンフも挙げられる。さらに、農業的および非農業的有害生物には、ハダニ科のハダニおよびアカダニ(リンゴハダニ(Panonychus ulmi コッチ(Koch))、ナミハダニ(Tetranychus urticae コッチ(Koch))、マクダニエルダニ(Tetranychus mcdanieli マクレガー(McGregor))など)、ヒメハダニ科のヒメハダニ(カンキツヒメハダニ(Brevipalpus lewisi マクレガー(McGregor))など)、フシダニ科のサビダニおよびフシダニならびに他の食葉性ダニなどのコナダニ(ダニ)ならびに、人間および動物の健康にとって重要なダニすなわち、チリダニ科のヒョウダニ、ニキビダニ科のニキビダニ、ニクダニ科のムギコナダニ、マダニ科のマダニ(シカダニ(Ixodes scapularis セイ(Say))、オーストラリアマダニ(Ixodes holocyclus ニューマン(Neumann))、カクマダニ(Dermacentor variabilis セイ(Say))、ローンスターチック(lone star tick)(Amblyomma americanum リンネ(Linnaeus))、キュウセンダニ科、シラミダニ科、ヒゼンダニ科の疥癬や皮癬のダニの成虫および幼虫;バッタ、イナゴおよびコオロギ(クルマバッタ(Melanoplus sanguinipes ファブリシウス(Fabricius)、M.differentialis トーマス(Thomas))、アメリカイナゴ(Schistocerca americana ドルーリー(Drury)など)、サバクバッタ(Schistocerca gregaria フォースカル(Forskal))、トノサマバッタ(Locusta migratoria リンネ(Linnaeus))、ブッシュロウカスト(busu locust)(Zonocerus spp.)、ヨーロッパイエコオロギ(Acheta domesticus リンネ(Linnaeus))、ケラ(Gryllotalpa spp.)など)をはじめとする直翅目の成虫および幼若虫;ハモグリムシ、ユスリカ、ミバエ(ミバエ科)、キモグリバエ(Oscinella frit リンネ(Linnaeus))、ウジバエ、イエバエ(Musca domestica リンネ(Linnaeus)など)、ヒメイエバエ(Fannia canicularis リンネ(Linnaeus)、F.femoralis ステイン(Stein)など)、サシバエ(Stomoxys calcitrans リンネ(Linnaeus))、イエバエの一種(face fly)、ノサシバエ、クロバエ(Chrysomya spp.、Phormia spp.)および他のイエバエ(muscoid)害虫、アブ(Tabanus spp.など)、ウマバエ(Gastrophilus spp.、Oestrus spp.など)、ウシバエ(Hypoderma spp.など)、メクラアブ(Chrysops spp.)、ヒツジシラミバエ(Melophagus ovinus リンネ(Linnaeus)など)ならびに他の短角亜目、カ(Aedes spp.、Anopheles spp.、Culex spp.など)、ブユ(Prosimulium spp.、Simulium spp.など)、クロヌカカ、スナバエ、sciaridsおよび他の長角亜目をはじめとする双翅目の成虫および幼若虫;ネギアザミウマ(Thrips tabaci リンデマン(Lindeman))、フラワースリップ(flower thrips)(Frankliniella spp.)および他の食葉性アザミウマをはじめとする総翅目の成虫および幼若虫;アリ(アカオオアリ(Camponotus ferrugineus ファブリシウス(Fabricius))、クロオオアリ(Camponotus pennsylvanicus デ・ギーア(De Geer))、イエヒメアリ(Monomorium pharaonis リンネ(Li
nnaeus))、チビヒアリ(Wasmannia auropunctata Roger)、アカカミアリ(Solenopsis geminata ファブリシウス(Fabricius))、ヒアリ(Solenopsis invicta ブレン(Buren))、アルゼンチンアリ(Iridomyrmex humilis メイル(Mayr))、アシナガキアリ(Paratrechina longicornis ラトレイル(Latreille))、トビイロシワアリ(Tetramorium caespitum リンネ(Linnaeus))、ヒメトビイロケアリ(Lasius alienus フォースター(Forster))、コヌカアリ(Tapinoma sessile セイ(Say)))、ハチ(クマバチを含む)、ホーネット(hornet)、イエロージャケット(yellow jacket)、大形のハチ(wasp)、および、ソーフライ(sawflies)(Neodiprion spp.;Cephus spp.)をはじめとするハチ目の昆虫害虫;ミゾガシラシロアリ(Reticulitermes flavipes コラー(Kollar))、セイヨウシロアリ(Reticulitermes hesperus バンクス(Banks))、イエシロアリ(Coptotermes formosanus シラキ(Shiraki))、ハワイシロアリ(Incisitermes immigrans シンダー(Snyder))および他の経済的観点から重要であるシロアリなどのシロアリ目の昆虫害虫;セイヨウシミ(Lepisma saccharina リンネ(Linnaeus))、マダラシミ(Thermobia domestica パッカード(Packard))などのシミ目の昆虫害虫;コロモジラミ(Pediculus humanus capitis デ・ギーア(De Geer))、アタマジラミ(Pediculus humanus humanus リンネ(Linnaeus))、ニワトリハジラミ(Menacanthus stramineus ニッツ(Nitszch))、イヌハジラミ(Trichodectes canis デ・ギーア(De Geer))、fluff louse(Goniocotes gallinae デ・ギーア(De Geer))、ヒツジハジラミ(Bovicola ovis シュランク(Schrank))、ウシジラミ(short−nosed cattle louse)(Haematopinus eurysternus ニッツ(Nitszch))、ウシジラミ(long−nosed cattle louse)(Linognathus vituli リンネ(Linnaeus))ならびに、人間や動物につく他の吸血シラミおよびハジラミを含むハジラミ目の昆虫害虫;ケオプスネズミノミ(Xenopsylla cheopis ロッシュチャイルド(Rothschild))、ネコノミ(Ctenocephalides felis ブーシュ(Bouche))、イヌノミ(Ctenocephalides canis カーティス(Curtis))、ニワトリノミ(Ceratophyllus gallinae シュランク(Schrank))、ニワトリフトノミ(Echidnophaga gallinacea ウェストウッド(Westwood))、ヒトノミ(Pulex irritans リンネ(Linnaeus))および人間や鳥を悩ます他のノミを含むノミ目の昆虫害虫が挙げられる。包含されるさらに他の節足動物害虫として、ドクイトグモ(Loxosceles reclusa グレッチュおよびミュレイク(Gertsch & Mulaik))ならびにクロゴケグモ(Latrodectus mactans ファブリシウス(Fabricius))などのクモ目のクモ、イエムカデ(Scutigera coleoptrata リンネ(Linnaeus))などの唇脚綱ゲジ目のムカデが挙げられる。また、本発明の化合物は、経済的観点から重要な農業害虫(すなわち、ネコブセンチュウ属の根こぶ線虫、ネグサレセンチュウ属の根ぐされ線虫、ユミハリセンチュウ属のユミハリ線虫など)ならびに動物および人間の健康を害する害虫(すなわち、経済的観点から重要なあらゆる吸虫、条虫および回虫であり、ウマの普通円虫(Strongylus vulgaris)、イヌの犬回虫(Toxocara canis)、ヒツジの捻転胃虫(Haemonchus contortus)、イヌの犬糸状虫(Dirofilaria immitis レイディ(Leidy))、ウマの葉状条虫(Anoplocephala perfoliata)、反芻動物の肝蛭虫(Fasciola hepatica リンネ(Linnaeus))など)などであるがこれに限定されるものではない、円虫目、回虫目、蟯虫目、ラブジチダ目、センビセンチュウ目、エノプルス目の経済的観点から重要な虫類をはじめとする、線虫綱、条虫綱、吸虫綱および鉤頭動物門の虫類にも活性も有する。
試験A
コナガ(Plutella xylostella)の防除を評価するために、12〜14日齢ラディッシュ植物を内部に含む小型開放容器で試験ユニットを構成した。コアサンプラーの使用により、昆虫食餌の一片において10〜15個体の新生幼虫で、これを事前に外寄生させ、シート上に多くの発育幼虫を有する硬化した昆虫食餌のシートからプラグを取り出し、そして幼虫および食餌を含有するプラグを試験ユニットに移した。食餌プラグが乾燥すると、幼虫は試験植物上へと移動した。
ヨトウガの一種(Spodoptera frugiperda)の防除を評価するために、4〜5日齢コーン(トウモロコシ)植物を内部に含む小型開放容器で試験ユニットを構成した。昆虫食餌の一片において10〜15個体の1日齢幼虫で、(コアサンプラーの使用により)これを事前に外寄生させた。
接触および/または浸透移行性手段によるモモアカアブラムシ(Myzus persicae)の防除を評価するために、12〜15日齢ラディッシュ植物を内部に含む小型開放容器で試験ユニットを構成した。培養植物から切除した葉の一片上の30〜40個体のエイフィッドを試験植物の葉の上に置くことにより、これを事前に外寄生させた(カットリーフ法)。葉の一片が乾燥すると、幼虫は試験植物上へと移動した。事前外寄生後、試験ユニットの土を砂の層で覆った。
接触および/または浸透移行性手段によるジャガイモヒメヨコバイ(Empoasca fabae Harris)の防除を評価するために、5〜6日齢ロンジオビーン(Longio bean)植物(出現した初生葉)を内部に含む小型開放容器で試験ユニットを構成した。適用前に、土の上部に白砂を加え、そして初生葉の一枚を切除した。試験Cに記載された通り試験化合物を配合し、250ppmで噴霧し、そして適用を3回繰り返した。噴霧後、5個体のジャガイモヒメヨコバイ(18〜21日齢成虫)によってそれらを後外寄生させる前に、試験ユニットを1時間乾燥させた。黒色のスクリーンキャップをシリンダーの上部に置いた。19℃〜21℃および50%〜70%相対湿度で育成チャンバー中に6日間、試験ユニットを保持した。次いで、昆虫死亡率に関して各試験ユニットを視覚的に評価した。
接触および/または浸透移行性手段によるワタアブラムシ(Aphis gossypii)の防除を評価するために、6〜7日齢綿植物を内部に含む小型開放容器で試験ユニットを構成した。試験Cに記載されたカットリーフ法に従って、葉の一片上に30〜40個体で、これを事前に外寄生させ、そして試験ユニットの土を砂の層で覆った。
接触および/または浸透移行性手段によるトウモロコシウンカ(Peregrinus maidis)の防除を評価するために、3〜4日齢コーン(トウモロコシ)植物(穂)を内部に含む小型開放容器で試験ユニットを構成した。適用前に、土の上部に白砂を加えた。試験Cに記載された通り試験化合物を配合し、250ppmで噴霧し、そして適用を三回繰り返した。噴霧後、サンドシェーカーによって砂上にそれらを振り撒くことによって、10〜20個体のコーンプラントホッパー(18〜20日齢若虫)によってそれらを後外寄生させる前に、試験ユニットを1時間乾燥させた。黒色のスクリーンキャップをシリンダーの上部に置いた。19℃〜21℃および50%〜70%相対湿度で育成チャンバー中に6日間、試験ユニットを保持した。次いで、昆虫死亡率に関して各試験ユニットを視覚的に評価した。
タバココナジラミ(Bemisia tabaci)の防除を評価するために、試験ユニットは、葉の裏面で2齢および3齢若虫により外寄生された少なくとも2枚の本葉を含む、レジ−アース(Redi−earth)(登録商標)培地(スコッツ・カンパニー(Scotts Co.))において育成された14〜21日齢綿植物からなる。
植物における化合物の移動、ならびに植物を通して化合物の葉部移動後のモモアカアブラムシ(Myzus persicae)およびジャガイモヒメヨコバイ(Empoasca fabae)の防除を評価するために、12〜15日齢ラディッシュ植物(モモアカアブラムシ試験のために)または5〜6日齢ロンジオビーン(Longio bean)植物(ジャガイモヒメヨコバイ試験のために)を含む小型開放容器で試験ユニットを構成した。
植物における化合物の移動、ならびに根部を通して葉部中への土壌適用から化合物の木部移動後のモモアカアブラムシ(Myzus persicae)およびジャガイモヒメヨコバイ(Empoasca fabae)の防除を評価するために、12〜15日齢ラディッシュ植物(モモアカアブラムシ試験のために)または5〜6日齢ロンジオビーン(Longio bean)植物(ジャガイモヒメヨコバイ試験のために)を含む小型開放容器で試験ユニットを構成した。
[式中、
R1はMe、Cl、BrまたはFであり、
R2はF、Cl、Br、C1〜C4ハロアルキルまたはC1〜C4ハロアルコキシであり、
R3はF、ClまたはBrであり、
R4はH;それぞれ場合によりハロゲン、CN、SMe、S(O)Me、S(O)2MeおよびOMeよりなる群から選択される1個の置換基によって置換されていてもよい、C1〜C4アルキル、C3〜C4アルケニル、C3〜C4アルキニル、C3〜C5シクロアルキルまたはC4〜C6シクロアルキルアルキルであり、
R5はHまたはMeであり、
R6はH、FまたはClであり、そして
R7はH、FまたはClである]
の化合物、そのN−オキシドまたは塩。
R2がCl、Br、CF3、OCF2H、OCF3またはOCH2CF3であり、そして
R4がH、Me、Et、i−Pr、t−Bu、CH2CN、CH(Me)CH2SMeまたはC(Me)2CH2SMe
である上記1項に記載の化合物。
R4がH、Me、Etまたはi−Prであり、そして
R5がHである
上記2項に記載の化合物。
(b)噴射剤と
を含んでなる噴霧組成物。
(b)1種もしくはそれ以上の食物材料と、
(c)場合により誘引剤と、
(d)場合により保湿剤と
を含んでなる餌料組成物。
(b)餌料組成物を受け取るように構成されたハウジングであって、ハウジングの外側の位置から無脊椎有害生物が餌料組成物に接近することができるように、無脊椎有害生物が開口を通過可能であるサイズに作られた少なくとも1つの開口を有し、かつ前記無脊椎有害生物の潜在的または既知の活性位置にまたはその付近に配置されるようにさらに構成されたハウジングと
を含んでなる無脊椎有害生物の防除装置。
Claims (8)
- 無脊椎有害生物またはその環境を請求項1に記載の化合物の生物学的に有効な量と接触させることを含んでなる無脊椎有害生物の防除方法。
- 該無脊椎有害生物がゴキブリ、アリまたはシロアリであり、該生物を、該化合物を含んでなる餌料組成物を消費することによって該化合物に接触させる請求項2に記載の方法。
- 無脊椎有害生物がカ、ブユ、サシバエ、メクラアブ、アブ、大型のハチ、イエロージャケット(yellow jacket)、ホーネット(hornet)、マダニ、クモ、アリまたはブヨであり、該生物を、噴霧容器から分配される該化合物を含んでなる噴霧組成物に接触させる請求項2に記載の方法。
- 請求項1に記載の化合物の生物学的に有効な量と、界面活性剤、固体希釈剤および液体希釈剤よりなる群から選択される少なくとも1種の追加成分とを含んでなり、場合により少なくとも1種の追加の生物学的に活性な化合物または薬剤の有効量をさらに含んでなる農業的または非農業的組成物。
- (a)請求項1に記載の化合物と、
(b)噴射剤と
を含んでなる噴霧組成物。 - (a)請求項1に記載の化合物と、
(b)1種もしくはそれ以上の食物材料と、
(c)場合により誘引剤と、
(d)場合により保湿剤と
を含んでなる餌料組成物。 - (a)請求項7に記載の餌料組成物と、
(b)餌料組成物を受け取るように構成されたハウジングであって、ハウジングの外側の位置から無脊椎有害生物が餌料組成物に接近することができるように、無脊椎有害生物が開口を通過可能であるサイズに作られた少なくとも1つの開口を有し、かつ該無脊椎有害生物の潜在的または既知の活性位置にまたはその付近に配置されるようにさらに構成されたハウジングと
を含んでなる無脊椎有害生物の防除装置。
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JP2008507582A (ja) * | 2004-07-26 | 2008-03-13 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー | アントラニルアミド無脊椎有害生物防除剤の混合物 |
JP2013028629A (ja) * | 2004-07-26 | 2013-02-07 | E I Du Pont De Nemours & Co | アントラニルアミド無脊椎有害生物防除剤の混合物 |
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