JP2021515020A - 殺真菌剤としてのピコリンアミド - Google Patents
殺真菌剤としてのピコリンアミド Download PDFInfo
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- JP2021515020A JP2021515020A JP2020546890A JP2020546890A JP2021515020A JP 2021515020 A JP2021515020 A JP 2021515020A JP 2020546890 A JP2020546890 A JP 2020546890A JP 2020546890 A JP2020546890 A JP 2020546890A JP 2021515020 A JP2021515020 A JP 2021515020A
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- JP
- Japan
- Prior art keywords
- hydrogen
- compound according
- alkyl
- powdery mildew
- plant
- 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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- 230000000855 fungicidal effect Effects 0.000 title claims abstract description 25
- 239000000417 fungicide Substances 0.000 title claims abstract description 25
- -1 Picoline amide Chemical class 0.000 title abstract description 145
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- 239000000203 mixture Substances 0.000 claims description 66
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- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 39
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- 230000002538 fungal effect Effects 0.000 claims description 31
- 238000000034 method Methods 0.000 claims description 29
- 229910052739 hydrogen Inorganic materials 0.000 claims description 28
- 239000001257 hydrogen Substances 0.000 claims description 28
- 125000000217 alkyl group Chemical group 0.000 claims description 24
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 claims description 23
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- 229910052757 nitrogen Inorganic materials 0.000 claims description 9
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- 230000012010 growth Effects 0.000 claims description 6
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- 125000003342 alkenyl group Chemical group 0.000 claims description 5
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- 206010039509 Scab Diseases 0.000 claims description 4
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- 239000000642 acaricide Substances 0.000 claims description 4
- 125000002252 acyl group Chemical group 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 235000009566 rice Nutrition 0.000 claims description 4
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
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- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
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- IZUPBVBPLAPZRR-UHFFFAOYSA-N pentachlorophenol Chemical compound OC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl IZUPBVBPLAPZRR-UHFFFAOYSA-N 0.000 description 6
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- QSOHVSNIQHGFJU-UHFFFAOYSA-L thiosultap disodium Chemical compound [Na+].[Na+].[O-]S(=O)(=O)SCC(N(C)C)CSS([O-])(=O)=O QSOHVSNIQHGFJU-UHFFFAOYSA-L 0.000 description 1
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- IQGKIPDJXCAMSM-UHFFFAOYSA-N triazoxide Chemical compound N=1C2=CC=C(Cl)C=C2[N+]([O-])=NC=1N1C=CN=C1 IQGKIPDJXCAMSM-UHFFFAOYSA-N 0.000 description 1
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- NRHFWOJROOQKBK-UHFFFAOYSA-N triphenyltin;hydrate Chemical compound O.C1=CC=CC=C1[Sn](C=1C=CC=CC=1)C1=CC=CC=C1 NRHFWOJROOQKBK-UHFFFAOYSA-N 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- PIHCREFCPDWIPY-UHFFFAOYSA-N tris[2-(2,4-dichlorophenoxy)ethyl] phosphite Chemical compound ClC1=CC(Cl)=CC=C1OCCOP(OCCOC=1C(=CC(Cl)=CC=1)Cl)OCCOC1=CC=C(Cl)C=C1Cl PIHCREFCPDWIPY-UHFFFAOYSA-N 0.000 description 1
- NCPXQVVMIXIKTN-UHFFFAOYSA-N trisodium;phosphite Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])[O-] NCPXQVVMIXIKTN-UHFFFAOYSA-N 0.000 description 1
- AQLJVWUFPCUVLO-UHFFFAOYSA-N urea hydrogen peroxide Chemical compound OO.NC(N)=O AQLJVWUFPCUVLO-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
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- WCJYTPVNMWIZCG-UHFFFAOYSA-N xylylcarb Chemical compound CNC(=O)OC1=CC=C(C)C(C)=C1 WCJYTPVNMWIZCG-UHFFFAOYSA-N 0.000 description 1
- 239000005943 zeta-Cypermethrin Substances 0.000 description 1
Classifications
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- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
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- C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
- C07C271/10—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C271/22—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of hydrocarbon radicals substituted by carboxyl groups
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- C—CHEMISTRY; METALLURGY
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
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- A01N53/00—Biocides, pest repellants or attractants, or plant growth regulators containing cyclopropane carboxylic acids or derivatives thereof
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- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B53/00—Asymmetric syntheses
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
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- C07C211/02—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
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- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C229/02—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
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- C07C229/08—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one amino and one carboxyl group bound to the carbon skeleton the nitrogen atom of the amino group being further bound to hydrogen atoms
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C229/02—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C229/28—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being saturated and containing rings
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- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
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- C07—ORGANIC CHEMISTRY
- 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
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- 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
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- 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
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Abstract
Description
本出願は、2018年3月8日に出願された米国仮特許出願第62/640424号、及び2018年3月8日に出願された米国仮特許出願第62/640434号の利益への優先権を主張するものであり、それらの開示は、その全体が参照により本明細書に組み込まれる。
[式中、
Qは、
であり、Xは、水素又はC(O)R4であり;
Yは、水素又はC(O)R4であり;
Zは、N又はN+→O−であり、Wは、O又はSであり;
R1は、水素又はアルキルであり、0、1つ、又は複数のR7で置換されており;
R2は、メチルであり;
R3は、アルキル、アリール、又はヘテロアリールから選択され、各々、0、1つ、又は複数のR7で任意選択的に置換されており;
R4は、アルコキシ又はベンジルオキシから選択され、各々、0、1つ、又は複数のR7で任意選択的に置換されており;
R5は、水素、アルコキシ、又はハロから選択され、各々、0、1つ、又は複数のR7で任意選択的に置換されており;
R6は、水素、−C(O)R8、又は−CH2OC(O)R8から選択され;
R7は、水素、アルキル、アリール、アシル、ハロ、アルケニル、アルキニル、アルコキシ、シアノ、又はヘテロシクリルから選択され、各々、0、1つ、又は複数のR9で任意選択的に置換されており;
R8は、アルキル、アルコキシ、又はアリールから選択され、各々、0、1つ、又は複数のR7で任意選択的に置換されており;
R9は、水素、アルキル、アリール、アシル、ハロ、アルケニル、アルコキシ、又はヘテロシクリルから選択され;
R10は、水素又はアルキルから選択され、各々、0、1つ、又は複数のR7で置換されている]の化合物を含んでもよい。
以下のスキームは、式(I)のピコリンアミド化合物を生成する手法を例示する。以下の記載及び実施例は、例示の目的で提供され、置換基又は置換パターンに関して限定するものとして解釈されるべきではない。
テトラヒドロフラン(THF)又はジエチルエーテル(Et2O)などの極性非プロトン性溶媒中において、約−78℃〜55℃の温度で、ハロゲン化アリールマグネシウムなどの有機金属求核試薬と反応させることで、式1.2−Rac、1.3−Rac、及び1.5−Rac、1.6−Rac[式中、R3は予め定義されたとおりである]のラセミ混合物を得て、これは工程aに示されている。
にさらすことにより、式1.2−Abs及び1.5−Abs[式中、R3は最初に定義されたとおりである]の未反応二級アルコール、並びに式2.1−Abs及び2.3−Abs[式中、R3は最初に定義されたとおりである]のアセチル化化合物を得る。混合物は、移動相としてヘキサン−酢酸エチル混合物を使用するシリカゲルクロマトグラフィーによって精製することができ、式1.2−Abs、1.5−Abs、2.1−Abs、及び2.3−Abs[式中、R3は最初に定義されたとおりである]の分割された二級アルコール及びアセテートを得て、これは高いエナンチオマー過剰率である。1.2−Rac、1.3−Rac、1.5−Rac、及び1.6−Rac[式中、R3は最初に定義されたとおりである]の二級アルコールのリパーゼ認識は、二級アルコールの速度論的光学分割についての経験則(Bornscheuer and Kazlauskus,Hydrolases in Organic Synthesis;Wiley−VCH,2006)と同様であった。式2.1−Abs及び2.3−Abs[式中、R3は最初に定義されたとおりである]のアセテートを、炭酸カリウムなどの炭酸塩基で、メタノールなどのアルコール溶媒中において、約25℃〜約60℃の温度で処理することより、式2.2−Abs及び2.4−Abs[式中、R3は最初に定義されたとおりである]の分割された二級アルコールを得る。
モノペルオキシフタル酸マグネシウム六水和物(MMPP)、ペルオキシ酢酸、オキソン、過塩素酸ナトリウム、又はジメチルジオキシランが挙げられるが、これらに限定されないその他の酸化剤を使用して調製してもよいことは、当業者に理解されるであろう。
新たに活性化されたマグネシウム金属削りくず(1.14g、46.80mmol)の無水Et2O(20mL)中懸濁液に、1−ブロモ−2,4−ジメチルベンゼン(8g、43.20mmol)を滴加した。混合物を、わずかな還流(36℃)で5時間(hr)穏やかに加熱した。−20℃のEt2O(50mL)中で懸濁したヨウ化銅(I)(4.12g、21.61mmol)入りフラスコに、得られた暗茶色溶液をシリンジで添加した。暗黄色懸濁液を、−20℃で15分(min)間撹拌し、次いで−50℃まで冷却した。ラセミトランス−ブテンエポキシド(1.3g、18.01mmol)を、ゆっくりと滴加し、続いて反応物を室温まで温めて、一晩撹拌した。次いで混合物を0℃まで冷却し、塩化アンモニウム(NH4Cl)飽和水溶液を添加することにより、ゆっくりとクエンチした。混合物をセライトパッドに通して濾過し、パッドを酢酸エチルで十分にすすいだ。有機溶液を、NH4Cl飽和溶液及びブラインで洗浄した。溶液を乾燥させ(硫酸マグネシウム(MgSO4))、濾過し、減圧下で濃縮した。残渣を、自動フラッシュカラムクロマトグラフィー(SiO2、0〜40%酢酸エチル/ヘキサン勾配)により精製して、ラセミトレオ−3−(2,4−ジメチルフェニル)ブタン−2−オールを黄色油状物として得た(813mg、25%):1H NMR(500MHz,CDCl3)δ 7.06(d,J=8.5Hz,1H),7.01−6.97(m,2H),3.94−3.82(m,1H),2.97(p,J=6.9Hz,1H),2.29(d,J=7.7Hz,6H),1.50(d,J=3.9Hz,1H),1.28(d,J=7.0Hz,3H),1.11(d,J=6.3Hz,3H);13C NMR(126MHz,CDCl3)δ 139.99,135.49,135.38,131.31,126.81,126.18,71.92,41.42,21.25,20.87,19.85,16.06;EIMS m/z 178.
−20℃のヨウ化銅(I)(4.15g、21.60mmol)の無水Et2O(40mL)中懸濁液に、2−メチルフェニルマグネシウムブロミド(Et2O中2.0M、22.5mL、43.20mmol)をゆっくりと滴加した。30分間撹拌した後、オレンジ色の懸濁液を−78℃まで冷却し、ラセミシス−ブテンエポキシド(1.3g、18.01mmol)をゆっくりと滴加した。ドライアイス浴を取り外し、混合物を周囲温度までゆっくりと温め、一晩撹拌した。混合物を氷浴で0℃まで冷却し、NH4Cl飽和水溶液を滴加することによりゆっくりとクエンチした。混合物を室温まで温め、セライトに通して濾過し、続いて酢酸エチル(EtOAc)でパッドをすすいだ。得られた濾液を、NH4Cl飽和水溶液及びブラインで洗浄した。次いで溶液を乾燥させ(MgSO4)、減圧下で濃縮した。残渣を、自動フラッシュカラムクロマトグラフィー(SiO2、0〜30%酢酸エチル/ヘキサン勾配)により精製し、ラセミエリスロ−3−(o−トリル)ブタン−2−オール(2.05g、69%)を黄色油状物として得た:1H NMR(500MHz,CDCl3)δ 7.34−7.01(m,4H),3.92(p,J=6.3Hz,1H),3.01(p,J=7.1Hz,1H),2.36(s,3H),1.47(s,1H),1.28(d,J=6.1Hz,3H),1.19(d,J=7.0Hz,3H);13C NMR(126MHz,CDCl3)δ 142.14,136.84,130.61,126.49,125.81,72.33,42.62,20.47,19.93,17.88;EIMS m/z 164.
ヨウ化銅(I)(1.86g、9.76mmol)のエチルエーテル(18.0mL)中懸濁液に、フェニルリチウム(ブチルエーテル中1.9M、10.3mL、19.53mmol)を、0℃で窒素雰囲気下にて滴加した。0℃で1時間撹拌した後、ラセミトランス−2,3−ジメチルオキシラン(0.64g、8.88mmol)を滴加し、続いて氷浴を取り外して、2時間にわたって撹拌しながら室温まで温めた。反応混合物を水(20mL)でクエンチし、セライトパッドに通して濾過し、エチルエーテル(3×20mL)で抽出した。有機物質を、相分離器に通し、減圧下で濃縮した。粗残渣を、自動フラッシュカラムクロマトグラフィー(SiO2、0〜25%アセトン/ヘキサン勾配)により精製し、ラセミトレオ−3−フェニルブタン−2−オール(1.33g、8.85mmol、99%)をオレンジ色油状物として得た:1H NMR(400MHz,CDCl3)δ 7.38−7.12(m,5H),3.91−3.84(m,1H),2.80−2.68(m,1H),1.43(s,1H),1.33(d,J=7.1Hz,3H),1.09(d,J=6.3Hz,3H).スペクトルデータは、文献:Tetrahedron 1981,37,709−713文献で報告されているものと一致していた。
工程1:(2S,3S)−3−(2,4−ジメチルフェニル)ブタン−2−オール及び(2R,3R)−3−(2,4−ジメチルフェニル)ブタン−2−イルアセテートの調製。
ビニルアセテート(15mL)中に溶解したラセミトランス−3−(2,4−ジメチルフェニル)ブタン−2−オール(800mg、4.49mmol)の溶液を入れたバイアルに、Novozym435リパーゼ(CAL−B、1.6g、4.49mmol)のビーズを充填した。バイアルをオービタルシェーカー内に入れ、200rpmで振盪させ、55℃で7.5時間加熱した。反応物を冷却し、EtOAcリンスと共にフリットディスクに通して濾過した。溶出液を減圧下で濃縮して、906mgの粗黄色油状物を得た。残渣を、フラッシュカラムクロマトグラフィー(SiO2、0〜20%酢酸エチル/ヘキサン勾配)により精製し、(2R,3R)−3−(2,4−ジメチルフェニル)ブタン−2−イルアセテート(透明油状物、466mg、47%)、続いて(2S,3S)−3−(2,4−ジメチルフェニル)ブタン−2−オール(透明黄色油状物、357mg、43%)を得た。アセテート:1H NMR(500MHz,CDCl3)δ 7.07(d,J=7.7Hz,1H),7.01−6.97(m,2H),5.08(dq,J=8.5,6.3Hz,1H),3.16−3.05(m,1H),2.30(s,3H),2.28(s,3H),2.06(s,3H),1.21(d,J=6.9Hz,3H),1.06(d,J=6.3Hz,3H);13C NMR(126MHz,CDCl3)δ 170.80,138.92,135.56,135.42,131.22,126.93,126.33,75.09,39.48,21.34,20.89,19.88,18.34,17.96;EIMS m/z 220.アルコール:1H NMR(500MHz,CDCl3)δ 7.06(d,J=8.5Hz,1H),7.01−6.97(m,2H),3.88(tt,J=9.2,4.7Hz,1H),2.97(p,J=6.9Hz,1H),2.30(s,3H),2.28(s,3H),1.49(d,J=3.5Hz,1H),1.28(d,J=7.0Hz,3H),1.11(d,J=6.3Hz,3H);13C NMR(126MHz,CDCl3)δ 140.00,135.49,135.38,131.31,126.82,126.18,71.92,41.43,21.25,20.87,19.85,16.07;EIMS m/z 178.(2S,3S)−3−(2,4−ジメチルフェニル)ブタン−2−オールのエナンチオマー比は、エナンチオマーHPLC分離(210nm波長)で分析することにより、96:4であると決定された。
メタノール(4.2mL)中に溶解した上記で調製した(2R,3R)−3−(2,4−ジメチルフェニル)ブタン−2−イルアセテート(458mg、2.08mmol)入り溶液に、炭酸カリウム(431mg、3.12mmol)を添加した。混合物を周囲温度で1.5時間撹拌し、次いで50℃まで2時間加熱した。反応物を冷却し、減圧下で濃縮した。残渣をアセトンで希釈し、シリカゲルの小さなプラグに通し、パッドをアセトンでよくすすいだ。溶媒を真空内で濃縮し、(2R,3R)−3−(2,4−ジメチルフェニル)ブタン−2−オール(332mg、90%)を黄色油状物として得た:1H NMR(500MHz,CDCl3)δ 7.06(d,J=8.5Hz,1H),7.01−6.97(m,2H),3.88(p,J=6.3Hz,1H),2.97(p,J=6.9Hz,1H),2.30(s,3H),2.28(s,3H),1.49(s,1H),1.28(d,J=7.0Hz,3H),1.11(d,J=6.3Hz,3H);13C NMR(126MHz,CDCl3)δ 140.00,135.49,135.38,131.31,126.82,126.18,71.92,41.43,21.26,20.87,19.85,16.07;EIMS m/z 178.アルコールのエナンチオマー比は、エナンチオマーHPLCによる分析により、7:93であると決定された。
塩化メチレン(7.7mL)中に溶解した(2S,3S)−3−フェニルブタン−2−オール(0.23g、1.53mmol)の溶液に、N−エチル−N’−(3−ジメチルアミノプロピル)カルボジイミドヒドロクロリド(0.59g、3.06mmol)及びN,N−ジメチルピリジン−4−アミン(19mg、0.15mmol)を添加した。反応混合物を窒素でパージし、16時間撹拌し、続いて真空内で濃縮した。粗残渣を、自動フラッシュカラムクロマトグラフィー(SiO2、0〜20%酢酸エチル/ヘキサン勾配)により精製し、(2S,3S)−3−フェニルブタン−2−イル(tert−ブトキシカルボニル)−L−アラニネート(0.43g、1.34mmol、83%収率)を無色油状物として得た:1H NMR(400MHz,CDCl3)δ 7.35−7.25(m,2H),7.27−7.15(m,3H),5.12−5.01(m,2H),4.35−4.26(m,1H),2.95−2.83(m,1H),1.45(s,9H),1.37(d,J=7.2Hz,3H),1.29(d,J=7.1Hz,3H),1.09(d,J=6.3Hz,3H);13C NMR(126MHz,CDCl3)δ 172.9,155.0,143.0,128.5,127.8,126.7,79.7,76.1,49.5,45.1,28.3,18.9,18.3,17.5;IR(薄膜)3355,2978,2934,1711,1495,1452,1366,1161,1087,1065,701cm−1.
工程1:(2S,3S)−3−フェニルブタン−2−イル−L−アラニネート・ヒドロクロリドの調製。
そのままの(2S,3S)−3−フェニルブタン−2−オール(tert−ブトキシカルボニル)−L−アラニネート(0.42g、1.31mmol)に、ジオキサン中に溶解したHCl溶液(4M、3.3mL、13.07mmol)を窒素下で滴加した。16時間撹拌したら、反応混合物を真空内で濃縮し、粗(2S,3S)−3−フェニルブタン−2−イル−L−アラニネート・塩化水素を白色固体として得て、これを次の工程に直接用いた:HRMS−ESI(m/z)[M+H]+C13H20NO2の計算値,222.1489;実測値,222.1485.
塩化メチレン(6.5mL)中に溶解した(2S,3S)−3−フェニルブタン−2−イル−L−アラニネート・塩化水素、3−ヒドロキシ−4−メトキシピコリン酸(0.24g、1.44mmol)、及び(ベンゾトリアゾール−1−イルオキシ)トリピロリジノホスホニウムヘキサフルオロホスフェート(0.75g、1.44mmol)の溶液に、N,N−ジイソプロピルエチルアミン(0.75mL、4.31mmol)を窒素下で滴加した。16時間撹拌したら、反応混合物を真空内で濃縮した。粗残渣を、自動フラッシュカラムクロマトグラフィー(SiO2、0〜45%アセトン/ヘキサン勾配)により精製し、(2S,3S)−3−フェニルブタン−2−イル(3−ヒドロキシ−4−メトキシピコリノイル)−L−アラニネート(0.46g、1.173mmol、90%収率)を無色油状物として得た:1H NMR(500MHz,CDCl3)δ 12.16(s,1H),8.50(d,J=8.0Hz,1H),8.01(d,J=5.2Hz,1H),7.32−7.27(m,2H),7.24−7.16(m,3H),6.88(d,J=5.2Hz,1H),5.11(dq,J=7.7,6.3Hz,1H),4.77−4.67(m,1H),3.95(s,3H),2.97−2.87(m,1H),1.54(d,J=7.2Hz,3H),1.31(d,J=7.0Hz,3H),1.13(d,J=6.3Hz,3H);IR(薄膜)2978,2937,1733,1647,1527,1451,1262,1147,701cm−1;HRMS−ESI(m/z)[M+H]+C20H25N2O5の計算値,373.1758;実測値,373.1752.
ピリジン(1.0mL)中に溶解した(2S,3S)−3−フェニルブタン−2−イル(3−ヒドロキシ−4−メトキシピコリノイル)−L−アラニネート(84mg、0.23mmol)含有溶液に、無水酢酸(0.25mL、2.65mmol)を窒素下で滴加した。30分間撹拌したら、反応混合物を真空内で濃縮し、続いてトルエン(10mL)と共沸させた。粗残渣を、自動フラッシュカラムクロマトグラフィー(SiO2、0〜40%アセトン/ヘキサン勾配)により精製し、(2S,3S)−3−フェニルブタン−2−イル(3−アセトキシ−4−メトキシピコリノイル)−L−アラニネート(90mg、0.21mmol、91%収率)を無色油状物として得た:1H NMR(500MHz,CDCl3)δ 8.56(s,1H),8.34(d,J=5.5Hz,1H),7.32−7.27(m,2H),7.24−7.16(m,3H),7.01(d,J=5.5Hz,1H),5.09(dq,J=7.7,6.3Hz,1H),4.77−4.67(m,1H),3.91(s,3H),2.96−2.86(m,1H),2.41(s,3H),1.49(d,J=7.2Hz,3H),1.30(d,J=7.0Hz,3H),1.10(d,J=6.3Hz,3H);IR(薄膜)3377,2980,2938,1770,1732,1674,1507,1310,1198,1174,702cm−1;HRMS−ESI(m/z)[M+H]+C22H27N2O6の計算値,415.1864;実測値,415.1859.
0.7mLのアセトン中に溶解した(2S,3R)−3−(o−トリル)ブタン−2−イル(3−ヒドロキシ−4−メトキシピコリノイル)−L−アラニネートを含有する溶液に、炭酸カリウム(39mg、0.279mmol)、続いてブロモ酢酸エチル(27μL、0.279mmol)を添加した。溶液を50℃で1.5時間加熱した。反応混合物を冷却し、真空内で濃縮した。粗残渣を、自動フラッシュカラムクロマトグラフィー(SiO2、0〜80%アセトン/ヘキサン勾配)により精製し、(2S,3R)−3−(o−トリル)ブタン−2−イル(3−(アセトキシメトキシ)−4−メトキシピコリノイル)−L−アラニネート(63mg、93%収率)を粘性油状物として得た:1H NMR(500MHz,CDCl3)δ 8.26(d,J=5.4Hz,1H),8.22(t,J=7.4Hz,1H),7.22−7.03(m,4H),6.93(d,J=5.4Hz,1H),5.73(dd,J=5.6,1.8Hz,2H),5.16(dq,J=8.1,6.3Hz,1H),4.58−4.51(m,1H),3.90(s,3H),3.31−3.22(m,1H),2.37(s,3H),2.06(s,3H),1.31(d,J=6.2Hz,3H),1.24(d,J=7.0Hz,3H),1.03(d,J=7.2Hz,3H);13C NMR(126MHz,CDCl3)δ 172.26,170.26,162.87,160.25,145.68,143.94,142.57,141.57,136.03,130.21,126.16,125.94,109.49,89.57,75.57,56.16,48.08,39.48,20.87,19.84,17.92,17.77,17.05;HRMS−ESI(m/z)[M+H]+C24H30N2O7の計算値,459.2126;実測値,459.2121.
(2S,3S)−3−(2−(トリフルオロメチル)フェニル)ブタン−2−イル(3−ヒドロキシ−4−メトキシピコリノイル)−L−アラニネート(283.9mg、0.645mmol)及びN,N−ジメチルピリジン−4−アミン(15.75mg、0.129mmol)を含有する溶液を、CH2Cl2(2mL)中で調製した。この溶液に、トリエチルアミン(0.180mL、1.289mmol)、続いてイソブチリルクロリド(0.102mL、0.967mmol)を添加した。得られた透明反応物を、周囲温度で一晩撹拌した。反応物を減圧下で濃縮し、N2流下で、オレンジ色油状物を得た。粗残渣を、自動フラッシュカラムクロマトグラフィー(SiO2、0〜100%酢酸エチル/ヘキサン勾配)により精製し、4−メトキシ−2−(((S)−1−オキソ−1−(((2S,3S)−3−(2−(トリフルオロメチル)フェニル)ブタン−2−イル)オキシ)プロパン−2−イル)カルバモイル)ピリジン−3−イルイソブチレート(252.3mg、0.494mmol、77%収率)を黄色油状物として得た:1H NMR(400MHz,CDCl3)δ 8.50(d,J=7.4Hz,1H),8.34(d,J=5.4Hz,1H),7.64(dd,J=8.0,1.3Hz,1H),7.54−7.47(m,1H),7.44(d,J=7.8Hz,1H),7.31(t,J=7.5Hz,1H),6.99(d,J=5.4Hz,1H),5.26−5.11(m,1H),4.76(p,J=7.3Hz,1H),3.89(s,3H),3.34(p,J=6.6Hz,1H),2.96(hept,J=7.0Hz,1H),1.54(d,J=7.2Hz,3H),1.36(dd,J=7.0,1.3Hz,6H),1.28(d,J=6.8Hz,3H),1.10(d,J=6.3Hz,3H);19F NMR(376MHz,CDCl3)δ −58.25;IR(薄膜)3383,2981,1737,1679,1505,1310,1114,1045,732cm−1;HRMS−ESI(m/z)[M+H]+C25H30F3N2O6の計算値,511.2050;実測値,511.2048.
工程1:(2S,3S)−3−(2−(トリフルオロメチル)フェニル)ブタン−2−イル(3−ヒドロキシ−4−メトキシピリジン−2−カルボノチオイル)−L−アラニネートの調製。
アセトニトリル(2.73mL)中に溶解した(2S,3S)−3−(2−(トリフルオロメチル)フェニル)ブタン−2−イル(3−ヒドロキシ−4−メトキシピコリノイル)−L−アラニネート(120.1mg、0.273mmol)含有溶液に、五硫化リン(121mg、0.545mmol)を添加し、続いて1,1,1,3,3,3−ヘキサメチルジシロキサン(291μL、1.363mmol)を一度に添加した。反応物を30分間で45℃に加熱し、反応物を冷却し、CH2Cl2(10mL)で希釈し、NaHCO3(10mL)飽和水溶液を添加することによりクエンチした。層を分離し、水層をCH2Cl2(3×10mL)で抽出した。合わせた有機層を、相分離器に通し、黄色油状物まで濃縮した。粗物質を、自動フラッシュカラムクロマトグラフィー(SiO2、0〜50%アセトン/ヘキサン勾配)により精製し、(2S,3S)−3−(2−(トリフルオロメチル)フェニル)ブタン−2−イル(3−ヒドロキシ−4−メトキシピリジン−2−カルボノチオイル)−L−アラニネート(104.7mg、0.229mmol、84%収率)を黄色半固体として得た;1H NMR(400MHz,CDCl3)δ 12.93(s,1H),10.74(d,J=7.6Hz,1H),8.00(d,J=5.1Hz,1H),7.73−7.59(m,1H),7.51(t,J=7.7Hz,1H),7.43(d,J=7.8Hz,1H),7.33(t,J=7.5Hz,1H),6.89(d,J=5.1Hz,1H),5.30−5.18(m,1H),5.14(p,J=7.2Hz,1H),3.96(s,3H),3.37(p,J=6.8Hz,1H),1.69(dd,J=7.2,3.2Hz,3H),1.30(d,J=6.8Hz,3H),1.14(d,J=6.3Hz,3H);19F NMR(376MHz,CDCl3)δ −58.23;IR(薄膜)3087,2984,1737,1513,1484,1311,1151,1118,800,771cm−1;HRMS−ESI(m/z)[M+H]+C21H24F3N2O4Sの計算値,457.1403;実測値、457.1399.
CH2Cl2(2mL)中に溶解した(2S,3S)−3−(2−(トリフルオロメチル)フェニル)ブタン−2−イル(3−ヒドロキシ−4−メトキシピリジンe−2−カルボノチオイル)−L−アラニネート(53.9mg、0.118mmol)及びN,N−ジメチルピリジン−4−アミン(2.89mg、0.024mmol)含有溶液に、トリエチルアミン(0.041mL、0.295mmol)、続いてアセチルクロリド(9.23μL、0.130mmol)を添加した。得られたライトオレンジ色反応物を、周囲温度で18時間撹拌した。反応物を減圧下で濃縮し、N2流下で、オレンジ色油状物を得た。粗残渣を、自動フラッシュカラムクロマトグラフィー(SiO2、0〜50%アセトン/ヘキサン勾配)により精製し、(2S,3S)−3−(2−(トリフルオロメチル)フェニル)ブタン−2−イル(3−アセトキシ−4−メトキシピリジン−2−カルボノチオイル)−L−アラニネート(51.7mg、0.104mmol、88%収率)を黄色油状物として得た:1H NMR(400MHz,CDCl3)δ 9.96(d,J=7.3Hz,1H),8.34(d,J=5.5Hz,1H),7.71−7.59(m,1H),7.59−7.47(m,1H),7.44(d,J=7.8Hz,1H),7.39−7.28(m,1H),7.00(d,J=5.5Hz,1H),5.28−5.15(m,2H),3.91(s,3H),3.42−3.29(m,1H),2.37(s,3H),1.64(d,J=7.2Hz,3H),1.30(d,J=6.8Hz,3H),1.12(d,J=6.3Hz,3H);19F NMR(376MHz,CDCl3)δ −58.23;HRMS−ESI(m/z)[M+H]+C23H26F3N2O5Sの計算値,499.1509;実測値,499.1508.
塩化メチレン(1.0mL)中に溶解した(2S,3S)−3−フェニルブタン−2−イル(3−ヒドロキシ−4−メトキシピコリノイル)−L−アラニネート(54mg、0.15mmol)含有溶液に、m−CPBA(50mg、0.29mmol)を添加した。30分間室温で撹拌したら、反応混合物を真空内で濃縮した。粗残渣を、自動フラッシュカラムクロマトグラフィー(SiO2、0〜50%アセトン/ヘキサン勾配)により精製し、3−ヒドロキシ−4−メトキシ−2−(((S)−1−オキソ−1−(((2S,3S)−3−フェニルブタン−2−イル)オキシ)プロパン−2−イル)カルバモイル)ピリジン1−オキシド(51mg、0.13mmol、86%収率)を粘稠な淡黄色油状物として得た:1H NMR(500MHz,CDCl3)δ 14.39(s,1H),12.82(d,J=6.9Hz,1H),7.89(d,J=7.2Hz,1H),7.32−7.25(m,2H),7.25−7.15(m,3H),6.78(d,J=7.2Hz,1H),5.10(dq,J=8.1,6.3Hz,1H),4.75−4.64(m,1H),3.97(s,3H),2.96−2.86(m,1H),1.56(d,J=7.2Hz,3H),1.30(d,J=6.9Hz,3H),1.12(d,J=6.2Hz,3H);IR(薄膜)2978,2937,1735,1643,1569,1479,1452,1211,1154,729,702cm−1;HRMS−ESI(m/z)[M+H]+C20H25N2O6の計算値,389.1707;実測値,389.1703.
塩化メチレン(1.0mL)中に溶解した(2S,3S)−3−フェニルブタン−2−イル(3−ヒドロキシ−4−メトキシピコリノイル)−L−アラニネート(54mg、0.15mmol)及びトリホスゲン(86mg、0.29mmol)含有溶液に、ピリジン(0.1mL、1.24mmol)を添加した。45分間撹拌したら、反応混合物を、重炭酸ナトリウム飽和溶液(5mL)でクエンチし、塩化メチレン(3×5mL)で抽出した。有機物質を相分離器に通し、真空内で濃縮した。粗残渣を、自動フラッシュカラムクロマトグラフィー(SiO2、0〜40%アセトン/ヘキサン勾配)により精製し、(2S,3S)−3−フェニルブタン−2−イル(S)−2−(8−メトキシ−2,4−ジオキソ−2H−ピリド[2,3−e][1,3]オキサジン−3(4H)−イル)プロパノエート(41mg、0.10mmol、67%収率)をオフホワイトの発泡体として得た:1H NMR(500MHz,CDCl3)δ 8.61(d,J=5.3Hz,1H),7.24−7.17(m,2H),7.17−7.06(m,4H),5.61(q,J=7.1Hz,1H),5.16−5.06(m,1H),4.06(s,3H),2.93−2.83(m,1H),1.70(d,J=7.1Hz,3H),1.27(d,J=7.1Hz,3H),1.04(d,J=6.3Hz,3H);IR(薄膜)2978,2942,1769,1712,1602,1501,1371,1242,1081,702cm−1;HRMS−ESI(m/z)[M+H]+C21H23N2O6の計算値,399.1551;実測値,399.1549.
工業銘柄の材料をアセトンに溶解させ、次いでこれを、110ppmのトリトンX−100を含有する9容量の水と混合した。殺真菌剤溶液を、自動吹付散布機(automated booth sprayer)を使用してコムギ実生に流出するまで施用した。散布された植物を、全て、更なる取り扱いの前に風乾した。特記しない限りは、全ての殺真菌剤を、前述の方法を使用して全ての標的の病気に対するこれらの活性について評価した。コムギの葉枯病及び褐色さび病の活性も、軌道散布施用(track spray application)を使用して評価し、この場合、0.1%のTrycol5941を散布液剤に含有するEC製剤として、殺真菌剤を製剤化した。
コムギ植物(品種Yuma)を、温室において50%鉱質土壌/50%無土壌Metroミックス中の種から、第一葉が完全に出現するまで、1ポットあたり7〜10個の実生で成長させた。これらの植物には、殺真菌剤処理の前又は後のいずれかにおいてプッシニア・トリチシナ(Puccinia triticina)の水性胞子懸濁液を接種した。接種した後、植物を100%の相対湿度で22℃の暗霧室に一晩保持して、胞子を発芽させ、葉を感染させた。次いで植物を、病気が発症するように、24℃に設定した温室に移した。殺真菌製剤、施用及び病気の評価は、実施例Aに記載された手順に従った。
工業銘柄の材料をアセトンに溶解させ、次いでこれを、0.011%のTween20を含有する9容量の水と混合した。殺真菌剤溶液を、自動吹付散布機を使用してダイズ実生に流出するまで施用した。散布された植物を、全て、更なる取り扱いの前に風乾した。
トマト植物(品種Outdoor Girl)を、各々1個の植物を有するポットにより無土壌Metroミックスで繁殖させ、12〜14日齢の時に使用した。試験植物には、殺真菌剤処理の24時間後にアルテルナリア・ソラニ(Alternaria solani)の水性胞子懸濁液を接種した。接種した後、植物を100%の相対湿度で(20℃で暗霧チャンバーに1日、続いて点灯霧チャンバーに2〜3日間)保持して、胞子を発芽させ、葉を感染させた。次に植物を、病気が発症するように、22℃の成長室に移した。殺真菌製剤、施用及び散布葉における病気の評価は、実施例Aに記載された手順に従った。
テンサイ植物(品種HH88)を、無土壌Metroミックスで成長させ、試験する前に均一な植物サイズを維持するため、定期的に刈り込んだ。植物には、殺真菌剤処理の24時間後に胞子懸濁液を接種した。接種した植物を22℃の霧チャンバーに48時間保持し、次に病気の症状が完全に発現するまで、底を通気した透明なプラスチックフードの、24℃に設定した温室でインキュベートした。殺真菌製剤、施用及び散布葉における病気の評価は、実施例Aに記載された手順に従った。
キュウリ実生(品種Bush Pickle)を、各々1個の植物を有するポットにより無土壌Metroミックスで繁殖させ、12〜14日齢の時に試験に使用した。試験植物には、殺真菌剤処理の24時間後にコレトトリクム・ラゲナリウム(Colletotrichum lagenarium)の水性胞子懸濁液を接種した。接種した後、植物を100%の相対湿度で22℃の霧室に48時間保持して、胞子を発芽させ、葉を感染させた。次に植物を、病気が発症するように、22℃に設定した成長室に移した。殺真菌製剤、施用及び散布葉における病気の評価は、実施例Aに記載された手順に従った。
コムギ植物(品種Yuma)を、温室において50%鉱質土壌/50%無土壌Metroミックス中の種から、第一葉が完全に出現するまで、1ポットあたり7〜10個の実生で成長させた。これらの植物には、殺真菌剤処理の24時間後にパラスタゴノスポラ・ノドルム(Parastagonospora nodorum)の水性胞子懸濁液を接種した。接種した後、植物を100%の相対湿度で(20℃で暗霧チャンバーに1日、続いて点灯霧チャンバーに2日間)保持して、胞子を発芽させ、葉を感染させた。次いで植物を、病気が発症するように、20℃に設定した温室に移した。殺真菌製剤、施用及び病気の評価は、実施例Aに記載された手順に従った。
キュウリ実生(品種Bush Pickle)を、無土壌Metroミックスにおいて、1ポットあたり1個の植物で成長させ、12〜14日齢の時に試験に使用した。植物には、殺真菌剤処理の24時間後に胞子懸濁液を接種した。試験植物には、殺真菌剤処理の24時間後にシュードペロノスポラ・キュベンシス(Pseudoperonospora cubensis)の水性胞子懸濁液を接種した。接種した後、植物を100%の相対湿度で22℃の霧室に24時間保持して、胞子を発芽させ、葉を感染させた。次に植物を、病気が完全に発現するまで、20℃に設定した温室に移した。殺真菌製剤、施用及び散布葉における病気の評価は、実施例Aに記載された手順に従った。
イネ実生(品種Japonica)を、各々8〜14個の植物を有するポットにより無土壌Metroミックスで繁殖させ、12〜14日齢の時に試験に使用した。試験植物には、殺真菌剤処理の24時間後にピリキュラリア・オリゼ(Pyricularia oryzae)の水性胞子懸濁液を接種した。接種した後、植物を100%の相対湿度で22℃の霧室に48時間保持して、胞子を発芽させ、葉を感染させた。次に植物を、病気が発症するように、24℃に設定した温室に移した。殺真菌製剤、施用及び散布葉における病気の評価は、実施例Aに記載された手順に従った。
オオムギ実生(品種Harrington)を、各々8〜12個の植物を有するポットにより無土壌Metroミックスで繁殖させ、第一葉が完全に出現した時に試験に使用した。試験植物には、殺真菌剤処理の24時間後にリンコスポリウム・セカリス(Rhynchosporium secalis)の水性胞子懸濁液を接種した。接種した後、植物を100%の相対湿度で20℃の霧室に48時間保持した。次に植物を、病気が発症するように、20℃に設定した温室に移した。殺真菌製剤、施用及び散布葉における病気の評価は、実施例Aに記載された手順に従った。
ブドウ実生(品種Carignane)を、無土壌Metroミックスにおいて、1ポットあたり1個の植物で成長させ、およそ1か月齢の時に試験に使用した。植物を、殺真菌剤処理の24時間後に、感染葉から試験植物に胞子を振とうすることにより接種した。植物を、病気が完全に発症するまで、20℃に設定した温室に維持した。殺真菌製剤、施用及び散布葉における病気の評価は、実施例Aに記載された手順に従った。
Claims (28)
- 式(I)
[式中、
Qは、
であり;
Xは、水素又はC(O)R4であり;
Yは、水素又はC(O)R4であり;
Zは、N又はN+→O−であり、Wは、O又はSであり;
R1は、水素又はアルキルであり、0、1つ、又は複数のR7で置換されており;
R2は、メチルであり;
R3は、アルキル、アリール、又はヘテロアリールであり、各々、0、1つ、又は複数のR7で任意選択的に置換されており;
R4は、アルコキシ又はベンジルオキシであり、各々、0、1つ、又は複数のR7で任意選択的に置換されており;
R5は、水素、アルコキシ、又はハロであり、各々、0、1つ、又は複数のR7で任意選択的に置換されており;
R6は、水素、−C(O)R8、又は−CH2OC(O)R8であり;
R7は、水素、アルキル、アリール、アシル、ハロ、アルケニル、アルキニル、アルコキシ、シアノ、又はヘテロシクリルであり、各々、0、1つ、又は複数のR9で任意選択的に置換されており;
R8は、アルキル、アルコキシ、又はアリールであり、各々、0、1つ、又は複数のR7で任意選択的に置換されており;
R9は、水素、アルキル、アリール、アシル、ハロ、アルケニル、アルコキシ、又はヘテロシクリルであり;
R10は、水素又はアルキルであり、各々、0、1つ、又は複数のR7で置換されている]の化合物。 - R1及びR10が、水素又はアルキルから独立して選択される、請求項2に記載の化合物。
- R3がアリールであり、0、1つ、又は複数のR7で任意選択的に置換されている、請求項2に記載の化合物。
- R1及びR10が水素又はアルキルから独立して選択され、R3がアリールであり、0、1つ、又は複数のR7で任意選択的に置換されている、請求項2に記載の化合物。
- R1及びR10が、水素又はアルキルから独立して選択される、請求項6に記載の化合物。
- R3がアリールであり、0、1つ、又は複数のR7で任意選択的に置換されている、請求項6に記載の化合物。
- R1及びR10が水素又はアルキルから独立して選択され、R3がアリールであり、0、1つ、又は複数のR7で任意選択的に置換されている、請求項6に記載の化合物。
- ZがNである、請求項10に記載の化合物。
- WがOである、請求項11に記載の化合物。
- R5がアルコキシである、請求項12に記載の化合物。
- R6が水素である、請求項13に記載の化合物。
- R1及びR10が、水素又はアルキルから独立して選択される、請求項14に記載の化合物。
- R3がアリールであり、0、1つ、又は複数のR7で任意選択的に置換されている、請求項14に記載の化合物。
- R1及びR10が水素又はアルキルから独立して選択され、R3がアリールであり、0、1つ、又は複数のR7で任意選択的に置換されている、請求項14に記載の化合物。
- R6が、−C(O)R8又は
−CH2OC(O)R8から選択される、請求項13に記載の化合物。 - R1及びR10が、水素又はアルキルから独立して選択される、請求項18に記載の化合物。
- R3がアリールであり、0、1つ、又は複数のR7で任意選択的に置換されている、請求項18に記載の化合物。
- R1及びR10が水素又はアルキルから独立して選択され、R3がアリールであり、0、1つ、又は複数のR7で任意選択的に置換されている、請求項18に記載の化合物。
- 請求項1〜21の記載の化合物のいずれか1つを含む、殺真菌剤組成物。
- 前記組成物が、1つ以上の殺真菌剤、殺虫剤、殺線虫剤、殺ダニ剤、節足動物駆除剤、殺菌剤、及びこれらの組み合わせを更に含む、請求項22に記載の組成物。
- 請求項1〜21に記載の化合物のうちの少なくとも1つと、殺真菌剤、殺虫剤、殺線虫剤、殺ダニ剤、節足動物駆除剤、殺菌剤、及びこれらの組み合わせを含む別の殺有害生物剤との混合物を含む、真菌病原体の防除のための組成物。
- 前記真菌病原体が、コムギの葉枯病(チモセプトリア・トリチシ(Zymoseptoria tritici))、コムギ褐色さび病(プッシニア・トリチシナ(Puccinia triticina))、コムギ紋さび病(プッシニア・ストリイホルミス(Puccinia striiformis))、リンゴそうか病(ベンツリア・イナエクアリス(Venturia inaequalis))、トウモロコシの黒穂病(ウスチラゴマイジス(Ustilago maydis))、ブドウうどんこ病(ウンシヌラ・ネカトル(Uncinula necator))、オオムギ雲形病(リンコスポリウム・セカリス(Rhynchosporium secalis))、イネのいもち病(ピリキュラリア・オリゼ(Pyricularia oryzae))、ダイズのさび病(ファコプソラ・パキリジ(Phakopsora pachyrhizi))、コムギ包えい枯病(パラスタゴノスポラ・ノドルム(Parastagonospora nodorum))、コムギのうどんこ病(ブルメリアグラミニス分化型トリチシ(Blumeria graminis f.sp.tritici))、オオムギのうどんこ病(ブルメリアグラミニス分化型ホルデイ(Blumeria graminis f.sp.hordei))、ウリ科植物のうどんこ病(エリシフェ・シコラセアルム(Erysiphe cichoracearum))、ウリ科植物の炭疽病(コレトトリクム・ラゲナリウム(Colletotrichum lagenarium))、カエンサイの葉斑病(セルコスポラ・ベチコラ(Cercospora beticola))、トマトの夏疫病(アルテルナリア・ソラニ(Alternaria solani))、キュウリのベと病(シュードペロノスポラ・キュベンシス(Pseudoperonospora cubensis))、及びオオムギの網斑病(ピレノホラ・テレス(Pyrenophora teres))のうちの1つである、請求項24に記載の組成物。
- 前記真菌病原体が、コムギの葉枯病(チモセプトリア・トリチシ(Zymoseptoria tritici))、コムギ褐色さび病(プッシニア・トリチシナ(Puccinia triticina))、オオムギ雲形病(リンコスポリウム・セカリス(Rhynchosporium secalis))、イネのいもち病(ピリキュラリア・オリゼ(Pyricularia oryzae))、ダイズのさび病(ファコプソラ・パキリジ(Phakopsora pachyrhizi))、コムギ包えい枯病(パラスタゴノスポラ・ノドルム(Parastagonospora nodorum))、ウリ科植物の炭疽病(コレトトリクム・ラゲナリウム(Colletotrichum lagenarium))、カエンサイの葉斑病(セルコスポラ・ベチコラ(Cercospora beticola))、ブドウうどんこ病(ウンシヌラ・ネカトル(Uncinula necator))、キュウリのベと病(シュードペロノスポラ・キュベンシス(Pseudoperonospora cubensis))、及びトマトの夏疫病(アルテルナリア・ソラニ(Alternaria solani))のうちの1つである、請求項24に記載の組成物。
- 植物への真菌攻撃を防除及び予防するための方法であって、
殺真菌有効量の請求項1〜21のいずれか一項に記載の化合物のうちの少なくとも1つを、前記植物、前記植物に隣接する区域、前記植物の成長を支持するように適合された土壌、前記植物の根及び前記植物の葉のうちの少なくとも1つに施用する工程を含む、方法。 - 植物への真菌攻撃を防除及び予防するための方法であって、
殺真菌有効量の請求項22〜23のいずれか一項に記載の組成物のうちの少なくとも1つを、前記植物、前記植物に隣接する区域、前記植物の成長を支持するように適合された土壌、前記植物の根及び前記植物の葉のうちの少なくとも1つに施用する工程を含む、方法。
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AU2019231764A1 (en) | 2020-10-01 |
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US20230049481A1 (en) | 2023-02-16 |
CN115745877A (zh) | 2023-03-07 |
US20190276404A1 (en) | 2019-09-12 |
WO2019173665A1 (en) | 2019-09-12 |
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