JP4727994B2 - ビフェニル誘導体および殺真菌剤としてのそれらの使用 - Google Patents
ビフェニル誘導体および殺真菌剤としてのそれらの使用 Download PDFInfo
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- JP4727994B2 JP4727994B2 JP2004562754A JP2004562754A JP4727994B2 JP 4727994 B2 JP4727994 B2 JP 4727994B2 JP 2004562754 A JP2004562754 A JP 2004562754A JP 2004562754 A JP2004562754 A JP 2004562754A JP 4727994 B2 JP4727994 B2 JP 4727994B2
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- halogen
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- alkyl
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- 239000000417 fungicide Substances 0.000 title description 5
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical class C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 169
- 229910052736 halogen Inorganic materials 0.000 claims description 50
- 150000002367 halogens Chemical class 0.000 claims description 44
- 229910052739 hydrogen Inorganic materials 0.000 claims description 39
- 125000000217 alkyl group Chemical group 0.000 claims description 37
- 239000001257 hydrogen Substances 0.000 claims description 34
- 125000001424 substituent group Chemical group 0.000 claims description 32
- 239000000203 mixture Substances 0.000 claims description 27
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 21
- 238000000034 method Methods 0.000 claims description 19
- 229910052731 fluorine Inorganic materials 0.000 claims description 17
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 16
- 125000005103 alkyl silyl group Chemical group 0.000 claims description 12
- 150000002431 hydrogen Chemical class 0.000 claims description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
- 125000006583 (C1-C3) haloalkyl group Chemical group 0.000 claims description 9
- 125000003545 alkoxy group Chemical group 0.000 claims description 9
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical group C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 8
- 125000002947 alkylene group Chemical group 0.000 claims description 8
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims description 7
- 125000003342 alkenyl group Chemical group 0.000 claims description 7
- 125000003282 alkyl amino group Chemical group 0.000 claims description 7
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 6
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 6
- 125000004414 alkyl thio group Chemical group 0.000 claims description 6
- 239000011737 fluorine Substances 0.000 claims description 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 5
- 125000000304 alkynyl group Chemical group 0.000 claims description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
- 125000004995 haloalkylthio group Chemical group 0.000 claims description 4
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 3
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 3
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- 244000005700 microbiome Species 0.000 claims 2
- GXQFIWVTOAWXHU-UHFFFAOYSA-N 3-(difluoromethyl)-n-[2-[4-(3,3-dimethylbut-1-ynyl)phenyl]phenyl]-1-methylpyrazole-4-carboxamide Chemical compound FC(F)C1=NN(C)C=C1C(=O)NC1=CC=CC=C1C1=CC=C(C#CC(C)(C)C)C=C1 GXQFIWVTOAWXHU-UHFFFAOYSA-N 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 54
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- 241000196324 Embryophyta Species 0.000 description 33
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- 208000015181 infectious disease Diseases 0.000 description 30
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 27
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- 239000000460 chlorine Substances 0.000 description 21
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- 238000005507 spraying Methods 0.000 description 15
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- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 13
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- 125000001188 haloalkyl group Chemical group 0.000 description 12
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- 125000004432 carbon atom Chemical group C* 0.000 description 10
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- 240000003768 Solanum lycopersicum Species 0.000 description 9
- 229910052794 bromium Inorganic materials 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 8
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 8
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- 229910052938 sodium sulfate Inorganic materials 0.000 description 8
- 235000011152 sodium sulphate Nutrition 0.000 description 8
- 235000021307 Triticum Nutrition 0.000 description 7
- 125000001246 bromo group Chemical group Br* 0.000 description 7
- 125000001309 chloro group Chemical group Cl* 0.000 description 7
- 238000009472 formulation Methods 0.000 description 7
- 239000000843 powder Substances 0.000 description 7
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- 0 CCC(*(*)c(cccc1)c1-c(cc1)ccc1N)C1=C(C)*C(C)=N1 Chemical compound CCC(*(*)c(cccc1)c1-c(cc1)ccc1N)C1=C(C)*C(C)=N1 0.000 description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N DMSO Substances CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000002671 adjuvant Substances 0.000 description 6
- 125000004429 atom Chemical group 0.000 description 6
- 239000002585 base Substances 0.000 description 6
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 6
- 239000003480 eluent Substances 0.000 description 6
- 125000005843 halogen group Chemical group 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- 239000012074 organic phase Substances 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- 241000221785 Erysiphales Species 0.000 description 5
- 235000007340 Hordeum vulgare Nutrition 0.000 description 5
- 235000007688 Lycopersicon esculentum Nutrition 0.000 description 5
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 5
- 240000006365 Vitis vinifera Species 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 5
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 description 4
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 4
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 4
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 4
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 4
- 230000009471 action Effects 0.000 description 4
- 239000003513 alkali Substances 0.000 description 4
- 239000000969 carrier Substances 0.000 description 4
- 238000005859 coupling reaction Methods 0.000 description 4
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 4
- 125000000524 functional group Chemical group 0.000 description 4
- 230000000855 fungicidal effect Effects 0.000 description 4
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 4
- 239000000543 intermediate Substances 0.000 description 4
- 125000002346 iodo group Chemical group I* 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 239000002689 soil Substances 0.000 description 4
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- 238000012360 testing method Methods 0.000 description 4
- 229930192474 thiophene Natural products 0.000 description 4
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 4
- 229920002554 vinyl polymer Polymers 0.000 description 4
- MMRSOBKBJLVCIM-UHFFFAOYSA-N 2-(4-ethynylphenyl)aniline Chemical group NC1=CC=CC=C1C1=CC=C(C#C)C=C1 MMRSOBKBJLVCIM-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
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- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 3
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- 201000003075 Crimean-Congo hemorrhagic fever Diseases 0.000 description 3
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- 241001533598 Septoria Species 0.000 description 3
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- 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
- CWMFRHBXRUITQE-UHFFFAOYSA-N trimethylsilylacetylene Chemical group C[Si](C)(C)C#C CWMFRHBXRUITQE-UHFFFAOYSA-N 0.000 description 1
- 244000045561 useful plants Species 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/81—Amides; Imides
- C07D213/82—Amides; Imides in position 3
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- C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
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- C07C217/76—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings and etherified hydroxy groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
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- C07C219/32—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings and esterified hydroxy groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
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- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
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- C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
- C07C2601/08—Systems containing only non-condensed rings with a five-membered ring the ring being saturated
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Description
より好ましくは、R1は水素である。
好ましくは、R2は水素である。
好ましくは、R3は水素である。
好ましくは、R4は水素である。
好ましくは、R5は水素、または、ハロゲンである。
より好ましくは、R5は水素、または、フッ素である。
さらに好ましくは、R5は水素である。
好ましくは、nは0である。
好ましくは、XはOである。
より好ましいHalは、ブロモである。
表1
表12
表13
m.p.=融点 b.p.=沸点
s=単項 br=ブロード
d=二重項 dd=二重項の二重項
t=三重項 q=四重項
m=多重項 ppm=百万分率
表14
化学式(I)の化合物は、強塩基[例えば、NaH、または、ヘキサメチルジシラザンナトリウム]の存在下において、乾燥した極性溶媒[好ましくはTHF]中で、そして、−10℃からその溶媒の沸点[好ましくは周囲温度]で、化学式(II)の化合物と化学式Het−C(=O)OR’[式中、R’はC1-5アルキルである]の化合物との反応により調製することができる。J. Wang et al, Synlett 2001,1485 による論文は類似する調製の詳細を供する。
化学式(I)の化合物は、不活性な有機溶媒[例えば、酢酸エチル、ジクロロメタン、ジオキサン、または、DMF]中で、そして、−10℃からその溶媒の沸点[好ましくは周囲温度]で、化学式(II)の化合物と化学式Het−C(=O)OR’’[式中、R’’はOH、または、離核基、例えば、Cl、Br、F、または、OC(=O)C1-4アルキル]の化合物との反応により調製することができる。R’’がOHである場合、その反応は、活性化剤[例えば、BOP−Cl]、および、2当量の塩基[例えば、第3級アミン、無機炭酸塩、または、炭酸水素塩]の存在下において行われる。一方、R’’が、離核基である場合、その反応は、少なくとも1当量の塩基[例えば、ピリジン、第3級アミン、無機炭酸塩、または、炭酸水素塩]の存在下において行われる。
化学式(I)の化合物[式中、R1は前に定義した通りであるが、水素ではない]は、溶媒[例えば、ハロゲン化溶媒(例えば、ジクロロメタン)、エーテル、酢酸エチル、DMF、または、水(二相性混合物として、任意的に、転移触媒相、例えば、テトラブチルアンモニウム硫酸水素塩)の存在下において)]中で、および、塩基[例えば、第3級アミン、アルカリ炭酸塩、アルカリ炭酸水素塩、アルカリ水酸化物、または、NaH;L1が(CO)C1-4アルキルである場合、塩基無しで単に加熱するだけでよい]の存在下において、化学式(I)の化合物[式中R1は水素である]と化学式R1−L1[式中、R1は前に定義した通りであるが、水素ではなく、;そして、L1は離隔基、例えば、Cl、Br、I、スルホン酸塩(例えば、メシレート、または、トシレート)、または、OC(O)C1-4アルキルである]との反応により調製することができる。
化学式(I)の化合物は、Cu(I)および非プロトン性溶媒[例えば、環状エーテル、例えば、ジオキサン]の存在下において、上昇させた温度で、そして、好ましくは還流温度において、化学式(III )の化合物[式中、Halは、好ましくは、ブロモまたはヨードである]と化学式Het−C(=O)NH2とを反応させることにより調製することができる。好ましい条件は、リガンド−形成物質としての1,2−ジアミン(例えば、1,2−ジアミノシクロヘキサン、または、エチレンジアミン)、および、少なくとも1当量の塩基(例えば、アルカリ炭酸塩、または、アルカリリン酸塩)の存在下において、化学式(III )の化合物に対して2%から100%モル/モルで使用されるCuIである。A. Klapars et al. J. Am. Chem. Soc. 123,7727 (2001) による論文は、類似する調製の詳細を供する。
化学式(I)の化合物は、化学式(IV)の化合物
表A
2−アミノ−4’−エチニル−ビフェニル(0.30g)および1−メチル−3−トリフルオロメチル−4−クロロカルボニル−ピラゾール(0.33g)を氷で冷却しながら、THF中で混合し、それから、ピリジン(0.12ml)を加えた。周囲温度に温めた後、その懸濁液を、3.5時間撹拌し、水に注ぎ、そして、酢酸エチルで2回抽出した。その有機相を分離し、硫酸ナトリウムで乾燥させ、そして、その溶媒を蒸発させ、そして、シリカゲル(溶媒:ヘキサン:酢酸エチル 2:1)においてクロマトグラフィー精製を行い、0.4g(70.2%)の化合物No.1.01を産出した。
10mlのジクロロメタン中に溶解した1−メチル−3−トリフルオロメチル−4−ピロールカルボン酸(0.22g)に、トリエチルアミン(0.32ml)および2−アミノ−4’−トリメチルシリルエチニル−ビフェニル(0.3g)を加え、そして、最後に、氷で冷却しながら、ビス(2−オキソ−3−オキサゾリジニル)クロロホスフィン酸(0.29g)を加えた。18時間撹拌した後、その溶媒を減圧下で除去し、そして、その残渣を酢酸エチルで溶かした。水およびブラインで洗浄し、硫酸ナトリウムで乾燥させ、そして、その溶媒を蒸発させ、産出した0.45gの黄色の油を、シリカゲル(溶出剤:ヘキサン:酢酸エチル 2:1)におけるクロマトグラフにかけ、0.13g(26%)の化合物No.2.01を産出した。
0−5℃における5mlの乾燥THF中のNaH(46mg)に、10mlの乾燥THF中の2−N−ホルミルアミノ−4’−(プロピン−1−イル)−ビフェニル(0.3g)を加えた。その反応を、この温度で1時間保ち、そして、その後、1−メチル−3−トリフルオロメチル−4−クロロカルボニル−ピラゾール(0.372g)を加えた。生じた懸濁液を、室温で一昼夜撹拌し、ブラインに注ぎ、そして、酢酸エチルで抽出した。その溶媒を蒸発させ、そして、その残渣をメタノール中に入れ、そして、ナトリウムメチラート(10mg)を加えた。30分後、その混合物を、希HClで中和し、酢酸エチルで抽出し、そして、中性となるまで洗浄した。シリカゲル(溶出剤:酢酸エチル:ヘキサン 1:2)におけるクロマトグラフにかけ、そして、トルエン:ヘキサン(4:1)から再結晶させ、0.169gの化合物No.1.72を産出した。
エタノール(70ml)中の2−ニトロ−4’ホルミル−ビフェニル(2g)(WO9503290)(2−ブロモニトロベンゼンと4−ホルミル−フェニル−ボロン酸とのPd−触媒カップリングにより調製された)に、ヒドラジン水和物(95%)(1.32g)を加え、そして、生じた混合物を、それから5時間還流させた。その溶媒を、減圧下において蒸発させて乾燥させ、その残渣をDMSO(30ml)中に懸濁し、それから、アンモニア(25%)(3ml)および新鮮な調製したCuCl(80mg)を順番に加え、そして、最後に、テトラクロロメタン(3.8g)を水で冷却しながら滴下した。その混合物を室温で24時間撹拌し、そして、生じた緑色の懸濁液を水に注ぎ、ジクロロメタンで抽出し、水で洗浄し、そして、硫酸ナトリウムで乾燥させた。その溶媒を蒸発させ、そして、その残渣のシリカゲル(溶出剤:ヘキサン:酢酸エチル 4:1)におけるクロマトグラフィーにより、2−ニトロ−4’(2,2−ジクロロ)エチレン−ビフェニル(0.8g)、m.p.58−59℃を産出した。
工程(a)由来の2−ニトロ−4’(2,2−ジクロロ)エチレン−ビフェニル(0.76g)を50%エタノール(30ml)中に溶かし、還流温度に加熱した。それから、50%エタノール(10ml)中の2NのHCl(0.3ml)を滴下した。その反応混合物を、還流温度で4時間保ち、室温に冷却し、そして、ろ過した。そのろ液を、炭酸水素ナトリウムで中和し、酢酸エチルで2回抽出し、そして、その有機相を硫酸ナトリウムで乾燥させた。減圧下における、その溶媒の蒸発により、2−アミノ−4’(2,2−ジクロロ)エチレン−ビフェニル(0.62g)(化合物No.12.07)を産出した。
2−ブロモ−ニトロベンゼン(0.86g)、4−(トリメチルシリル)フェニルボロン酸(1g)、および、ビス−(トリフェニルホスフィン)−パラジウムジクロリド(0.3g)を、ジメトキシエタン(35ml)中に溶かし、それから、水(5ml)中に溶かした炭酸水素ナトリウム(1.3g)の溶液を滴下した。その混合物を3時間(80℃の湯浴温度)加熱し、室温に冷却し、酢酸:水::1:1(300ml)に注ぎ、そして、吸引ろ過した。その有機相を分離し、硫酸ナトリウムで乾燥させ、そして、その溶媒を除去した。生じた残渣(1.58gの濃い油)をシリカゲル(溶出剤:ヘキサン:酢酸エチル 4:1)におけるクロマトグラフにかけ、黄色の油(1.12g)を得た。この化合物は工程Bにおいて使用した。
上述の工程Aから得られた化合物(0.955g)およびギ酸アンモニウム(ammonium formiate)(1.86g)を、メタノール(30ml)中に溶かし、窒素でパージした。この溶液に、二分して、pd(100mg;炭素上10%)を加えた。室温で15時間撹拌後、反応混合物をろ過し、そして、その溶媒を蒸発させた。
化学式(I)の化合物の製剤、例えば、乳化性濃縮物、溶液、顆粒、粉末、および、湿潤性粉末の調製のための実験手順は、WO97/33890において説明されている。
実施例B−1:プッシニア・レコンジタ(Puccinia recondita)/小麦(小麦における褐サビ病)に対する作用
1週齢の小麦植物、cv.Arinaを、スプレーチャンバー中で、処方した試料化合物(0.02%の活性成分)で処理する。散布の翌日、その小麦植物に、胞子懸濁液(1×105胞子/ml)をスプレーすることにより接種する。20℃および95%r.h.での2日間のインキュベーション後、その植物を、グリーンハウスにおいて、20℃および60%r.h.で8日間保つ。接種から10日後、上記疾患の感染率を評価する。
5週齢のリンゴ苗木、cv.McIntoshをスプレーチャンバー中で、処方した試料化合物(0.02%の活性成分)で処理する。散布の翌日、そのリンゴ植物に、試験植物の上で、リンゴウドン粉病に感染した植物を振ることにより、リンゴ植物に接種する。14/10時間(明/暗)の明るさ管理下における、22℃および60%r.h.での12日間のインキュベーション後、上記疾患の発生率を評価する。
4週齢のリンゴ苗木、cv.McIntoshをスプレーチャンバー中で、処方した試料化合物(0.02%の活性成分)で処理する。散布の翌日、試験植物に、胞子懸濁液(4×105分生子/ml)をスプレーすることにより、リンゴ植物に接種する。20℃および95%r.h.での4日間のインキュベーション後、その植物を、グリーンハウス中、21℃および60%r.h.に4日間置く。21℃および95%r.h.でのインキュベーションからさらに4日後、上記疾患の発生率を評価する。
1週齢の大麦植物、cv.Reginaをスプレーチャンバー中で、処方した試料化合物(0.02%の活性成分)で処理する。散布の翌日、試験植物の上で、うどん粉病に感染した植物を振ることにより、大麦植物に接種する。グリーンハウス中、20℃/18℃(昼/夜)および60%r.h.での6日間のインキュベーション後、上記疾患の感染率を評価する。
5週齢のブドウ苗木、cv.Gutedelをスプレーチャンバー中で、処方した試料化合物(0.02%の活性成分)で処理する。散布から2日後、その試料植物上に胞子懸濁液(1×106分生子/ml)をスプレーすることにより、ブドウ植物に接種する。グリーンハウス中、21℃および95%r.h.での4日間のインキュベーション後、上記疾患の感染率を評価する。
4週齢のトマト植物、cv.Roter Gnomをスプレーチャンバー中で、処方した試料化合物(0.02%の活性成分)で処理する。散布から2日後、その試料植物上に胞子懸濁液(1×105分生子/ml)をスプレーすることにより、トマト植物に接種する。育成チャンバー中、20℃および95%r.h.での4日間のインキュベーション後、上記疾患の感染率を評価する。
1週齢の小麦植物、cv.Arinaをスプレーチャンバー中で、処方した試料化合物(0.02%の活性成分)で処理する。散布の翌日、その試料植物上に胞子懸濁液(5×105分生子/ml)をスプレーすることにより、小麦植物に接種する。20℃および95%r.h.での1日間のインキュベーション後、その植物を、グリーンハウス中、20℃および60%r.h.に10日間保つ。接種から11日後、上記疾患の感染率を評価する。
1週齢の大麦植物、cv.Reginaをスプレーチャンバー中で、処方した試料化合物(0.02%の活性成分)で処理する。散布から2日後、その試料植物上に胞子懸濁液(3×104分生子/ml)をスプレーすることにより、大麦植物に接種する。グリーンハウス中、20℃および95%r.h.での4日間のインキュベーション後、上記疾患の感染率を評価する。
4週齢のトマト植物、cv.Roter Gnomをスプレーチャンバー中で、処方した試料化合物(0.02%の活性成分)で処理する。散布から2日後、その試料植物上に胞子懸濁液(2×105分生子/ml)をスプレーすることにより、トマト植物に接種する。育成チャンバー中、20℃および95%r.h.での3日間のインキュベーション後、上記疾患の感染率を評価する。
5週齢のブドウ苗木、cv.Gutedelをスプレーチャンバー中で、処方した試料化合物(0.02%の活性成分)で処理する。散布の翌日、試験植物の上で、ブドウウドン粉病に感染した植物を振ることにより、ブドウ植物に接種する。14/10時間(明/暗)の明るさ管理下における、26℃および60%r.h.での7日間のインキュベーション後、上記疾患の発生率を評価する。
2週齢の小麦植物、cv.Ribandをスプレーチャンバー中で、処方した試料化合物(0.2%の活性成分)で処理する。散布の翌日、その試料植物上に胞子懸濁液(10×105分生子/ml)をスプレーすることにより、小麦植物に接種する。23℃および95%r.h.での1日間のインキュベーション後、その植物を、グリーンハウス中、23℃および60%r.h.に16日間保つ。接種から18日後、上記疾患の感染率を評価する。
Claims (10)
- 化学式(I)の化合物:
Hetは、ピラゾール、ピロールまたはチアゾール環であって、該環は、1つ、2つまたは3つのRy基で置換されており;
R1は、水素であり;
R2、R3およびR4は、それぞれ独立に、水素、ハロゲン、メチルまたはCF3であり;
R5は、水素またはフッ素であり;
各R6は、独立に、ハロゲン、メチルまたはCF3であり;
R7は、(Z)mC≡C(Y1)であり;
各Ryは、独立に、ハロゲン、C1-3アルキル、C1-3ハロアルキル、C1-3アルコキシ(C1-3)アルキレンまたはシアノであり;
Xは、Oであり;
Ylは、水素、ハロゲン、C1-4アルキル[ハロゲン、ヒドロキシ、C1-4アルコキシ、C1-4ハロアルコキシ、C1-4アルキルチオ、Cl-4ハロアルキルチオ、C1-4アルキルアミノ、ジ(C1-4)アルキルアミノ、Cl-4アルコキシカルボニルおよびトリ(C1-4)アルキルシリルからそれぞれ独立に選択される1又は複数の置換基により任意的に置換されている]、C2-4アルケニル[ハロゲンからそれぞれ独立に選択される1又は複数の置換基により任意的に置換されている]、C2-4アルキニル[ハロゲンからそれぞれ独立に選択される1又は複数の置換基により任意的に置換されている]、C3-7シクロアルキル[ハロゲン、C1-4アルキルおよびC1-4ハロアルキルからそれぞれ独立に選択される1又は複数の置換基により任意的に置換されている]、またはトリ(C1-4)アルキルシリルであり;
Zは、C1-4アルキレン[ヒドロキシ、シアノ、C1-4アルコキシ、C1-4ハロアルコキシ、C1-4アルキルチオ、COOHおよびCOO−C1-4アルキルからそれぞれ独立に選択される1又は複数の置換基により任意的に置換されている]であり;
mは、0または1であり;そして、
nは、0、1または2である、化合物。 - 上記式中、m=0である、請求項1に記載の化学式(I)の化合物。
- 上記式中、R7が4’位にある、請求項1に記載の化学式(I)の化合物。
- 上記式中、R5が水素である、請求項1に記載の化学式(I)の化合物。
- 上記式中、R2、R3およびR4が水素である、請求項4に記載の化学式(I)の化合物。
- 上記式中、n=0である、請求項1に記載の化学式(I)の化合物。
- 3−ジフルオロメチル−1−メチル−1H−ピラゾール−4−カルボン酸[4’−(3,3−ジメチル−ブト−1−イニル)−ビフェニル−2−イル]−アミドである、請求項1に記載の化合物。
- 微生物の制御、並びに、微生物による植物の攻撃および侵襲の予防のための組成物であって、適当な担体と一緒に、0.1〜99重量%の請求項1に記載の式(I)の化合物を含有する組成物。
- 1ヘクタールあたり5g〜2kgの請求項1に記載の化学式(I)の化合物を、植物に対して、その一部に対して、またはその場所に対して適用することにより、病原性微生物による栽培した植物の侵襲を、制御または防止する方法。
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GBGB0230155.4A GB0230155D0 (en) | 2002-12-24 | 2002-12-24 | Chemical compounds |
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PCT/EP2003/014248 WO2004058723A1 (en) | 2002-12-24 | 2003-12-15 | Biphenyl derivatives and their use as fungicides |
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