JP6749002B2 - 植物成長促進剤及び植物成長促進方法 - Google Patents
植物成長促進剤及び植物成長促進方法 Download PDFInfo
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- LMMHUMUYOHSTKY-UHFFFAOYSA-N C(c1ccc2OCOc2c1)N1CCOCC1 Chemical compound C(c1ccc2OCOc2c1)N1CCOCC1 LMMHUMUYOHSTKY-UHFFFAOYSA-N 0.000 description 1
- 0 CC(*)(*)N1C(C)(*)C(C)(C)*C2(C)C1(C)*2 Chemical compound CC(*)(*)N1C(C)(*)C(C)(C)*C2(C)C1(C)*2 0.000 description 1
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Description
(1)次式(I):
NZは、窒素原子を介してC(R1)(R2)又はAr1に結合している、1又は2個の窒素原子を有する置換又は非置換の含窒素複素環基、又は次式(II):
R3、R4、R5及びR6は、それぞれ、水素原子又はメチル基であり;
R3とR4、及び/又はR5とR6は、共同してオキソ基を表してもよく;
R12及びR13は、それぞれ、水素原子、又は置換又は非置換のC1−3−アルキル基である。)
で示される基であり;
nは0、1又は2であり;
R1及びR2は、それぞれ、水素原子、置換又は非置換のC1−3−アルキル基、シアノ基又はカルボキシル基であり、R1及びR2は、共同してオキソ基を表してもよく、nが2のとき、R1同士又はR2同士は同一でも異なっていてもよい。]
で示される化合物又はその塩を含有する植物成長促進剤。
Xは、NR11(式中、R11は水素原子、又は置換又は非置換のC1−3−アルキル基である。)、酸素原子、硫黄原子、−SO2−、−SO−、メチレン基又は直接結合であり;
R3、R4、R5、R6、R7、R8、R9及びR10は、それぞれ、水素原子又はメチル基であり;
R3とR4、R5とR6、R7とR8、及び/又はR9とR10は、共同してオキソ基を表してもよい。)
で示される化合物又はその塩である前記(1)に記載の植物成長促進剤。
R3、R4、R5、R6、R7、R8、R9及びR10は、それぞれ、水素原子又はメチル基であり;
R3とR4、R5とR6、R7とR8、及び/又はR9とR10は、共同してオキソ基を表してもよい。)
で示される化合物又はその塩。
Ar3−O−CH2COOH
(式中、Ar3は1〜3個のハロゲン原子で置換されたフェニル基である。)
で示される化合物又はその塩と併用すると、カルスを誘導させることがあるが、前記合成オーキシンを使用しなければ、カルスを誘導させることはなく、植物成長促進作用を示す。
以下の化合物を用いて、本発明の植物成長促進剤の植物成長促進作用を検討した。
B−1.実験方法(1)
1/2MS培地(アガロース0.9%、シュークロース1.5%、Murashige & Skoog植物培養用培地×1/2濃度)を用意した。オートクレーブ後、各々に、被験化合物を60μM加えて、プラスチックシャーレ中で固化した。アラビドプシス種子(Columbia)をエタノールで滅菌した後、播種し、発芽後の葉、根、茎の状態を観察した。対照には溶媒として用いたDMSOのみを添加した。
1/2MS培地(アガロース0.9%、シュークロース1.5%、Murashige & Skoog植物培養用培地×1/2濃度)を用意した。オートクレーブ後、各々に、被験化合物を0(DMSOのみ)、15、30又は60μM加えて、プラスチックシャーレ中で固化した。アラビドプシス種子(Columbia)をエタノールで滅菌した後、播種し、発芽後の葉、根の状態を観察した。対照には溶媒として用いたDMSOのみを添加した。
1/2MS培地(アガロース0.9%、シュークロース1.5%、Murashige & Skoog植物培養用培地×1/2濃度)を用意した。オートクレーブ後、各々に、化合物1(PPZ)を0(DMSOのみ)、5、15又は30μM加えて、プラスチックポット中で固化した。トマト種子(Micro-Tom)を次亜塩素酸で滅菌した後、播種し、発芽後の葉、茎の状態を観察した。対照には溶媒として用いたDMSOのみを添加した。
イネ用培養土を植物ポットに用意し、イネ(日本晴)を播種した。発芽7日目までは、蒸留水で育成し、発芽7日目以降、化合物1(PPZ)を0(DMSOのみ)、15又は30μMの濃度で含む蒸留水をポットの下側から吸わせた。7日目毎に、古い水を捨て、新しい水に交換した。発芽21日目もしくは処理開始から14日目に写真撮影及び草丈測定を行った。
ナス型フラスコに水素化ホウ素ナトリウム(1.98g)とTHF(75ml)を入れて氷冷した。化合物a(2.03g)のTHF(25ml)溶液を一気に加え、ヨウ素(5.72g)のTHF(15ml)溶液をゆっくり30分かけて滴下した。その後、加熱還流で一晩撹拌した。氷冷してメタノールを発泡がおさまるまでゆっくり滴下して反応を終了した。その溶液からエバポレーターでTHFをある程度除き、反応液にジクロロメタンを加え1M-水酸化ナトリウム水溶液・飽和食塩水の順で洗浄し、硫酸Naで脱水し、濃縮してクロロホルム−メタノールを溶離液としたシリカゲルカラムクロマトグラフィー(WakosilTMC-300)で精製し、化合物bを得た。(収量1.09g;収率59%)
ナス型フラスコに化合物b(1.1g)、ジクロロメタン(15ml)、ピリジン(500μl)を入れ氷冷し、三臭化リン(1.0ml)をゆっくり加えた。5分後、室温にして2時間撹拌した。水で反応停止し、ジクロロメタンで抽出した。その後、飽和食塩水で洗浄し、硫酸Naで脱水し、濃縮して化合物cを得た。得られた化合物はそのまま次の反応に用いた。
1H NMR(CDCl3, 500MHz): δ=2.50(4H, br), 2.54(2H, m), 2.71(2H, m), 3.37(4H, t, J = 5.0 Hz), 5.91(2H, s), 6.64(1H, dd, J = 1.5, 8.0 Hz), 6.70(1H, d, J = 2.0 Hz), 6.72(1H, d, J = 8.0 Hz)
ナス型フラスコに化合物dとTHF(40ml)を入れ、窒素雰囲気下-78℃に冷やした。その溶液にメチルマグネシウムブロミドのTHF溶液(0.92mol/l、21ml)をゆっくり滴下した後、2時間撹拌した。反応溶液に水をゆっくり入れて反応停止し、常温に戻してからエバポレーターでTHFをある程度除いてから酢酸エチルで抽出した。その後、水・飽和食塩水の順で洗浄し、硫酸Naで脱水し、濃縮してヘキサン−酢酸エチルを溶離液としたシリカゲルカラムクロマトグラフィー(WakosilTMC-300)で精製し、化合物eを得た。(収量2.03g;収率86%)
ナス型フラスコに化合物e(205mg)とジクロロメタン(4.0ml)、トリフェニルホスフィン(0.98g)、四臭化炭素(1.21g)を入れ室温で5時間撹拌した。TLCに変化がなくなったのでモルホリン(3.65ml)を加えて一晩室温で撹拌した。反応液を酢酸エチルで抽出した。その後、水・飽和食塩水の順で洗浄し、硫酸Naで脱水し、濃縮してヘキサン−酢酸エチルを溶離液としたシリカゲルカラムクロマトグラフィー(WakosilTMC-300)で精製し、化合物17を得た。(収量90.7mg;収率31%)
1H NMR(CDCl3, 500MHz): δ=1.30(3H, d, J = 6.0 Hz), 2.33-2.45(4H, m), 3.21(1H, q, J = 6.5 Hz), 3.68(4H, t, J = 5.0 Hz), 5.93(2H, d, J = 1.5 Hz), 6.71-6.75(2H), 6.86(1H, s)
1H NMR(CDCl3, 500MHz): δ=2.24(3H, s), 2.58(2H, t, J = 8.0 Hz), 3.34 (3H, s), 3.46(2H, s), 3.50(2H, t, J = 6.0 Hz), 5.93(2H, s), 6.73(2H, d, J = 1.5 Hz), 6.84(1H, s)
ナス型フラスコに化合物j(1.5g)と硫酸(2.0ml)/メタノール(17ml)の混合溶液を入れ、一晩加熱還流した。反応液を酢酸エチルで抽出した。その後、飽和食塩水で洗浄し、硫酸Naで脱水し、濃縮してヘキサン−酢酸エチルを溶離液としたシリカゲルカラムクロマトグラフィー(WakosilTMC-300)で精製し、化合物kを得た。(収量1.69g;収率52%)
ナス型フラスコに化合物k(2.01g)とNBS(8.48g)、四塩化炭素(125ml)を加えた。その後、窒素雰囲気下でAIBN(340mg)を加えて44時間加熱還流をした。反応液をクロロホルムで抽出した。その後、飽和食塩水で洗浄し、硫酸Naで脱水し、濃縮してクロロホルムのみを溶離液としたシリカゲルカラムクロマトグラフィー(WakosilTMC-300)で精製し、化合物lを得た。(収量2.64g;収率73%)
ナス型フラスコに化合物l(2.64g)とアセトン(75ml)、ヨウ化ナトリウム(5.63g)を加え、3時間加熱還流した。反応液をジクロロメタンで抽出した。その後、飽和食塩水で洗浄し、硫酸Naで脱水し、濃縮してヘキサン−酢酸エチルを溶離液としたシリカゲルカラムクロマトグラフィー(WakosilTMC-300)で精製し、化合物mを得た。(収量1.03g;収率72%)
ナス型フラスコに1M-水素化アルミニウムリチウムのTHF溶液(1.0ml)とTHF(1.0ml)を入れ氷冷した。その溶液に化合物m(101mg)のTHF溶液(2.0ml)をゆっくり加え、そのまま30分撹拌した。反応溶液に水(35μl)・1N-NaOH(70μl)・水(100μl)の順に加え、酢酸エチルで薄めてからセライトでろ過をし、濃縮してそのまま次の反応に用いた。(粗収量86.4mg、粗収率101%)
ナス型フラスコに化合物n(86.4mg)、ジクロロメタン(1.0ml)、ピリジン(42μl)を入れ氷冷し、三臭化リン(25μl)をゆっくり加え、そのまま30分撹拌した。水で反応停止して反応液を酢酸エチルで抽出した。その後、飽和食塩水で洗浄し、硫酸Naで脱水し、濃縮して化合物oを得た。得られた化合物はそのまま次の反応に用いた。
1H NMR(CDCl3, 500MHz): δ=2.40(4H, br), 3.31(2H, s), 3.69(4H, t, J = 5.0 Hz), 5.85(2H, s), 6.54(1H, d, J = 8.0 Hz), 6.62(1H, d, J = 2.0 Hz), 6.74(1H, dd, J = 2.0, 8.0 Hz), 6.84(1H, s)
Claims (9)
- 次式(I):
NZは、窒素原子を介してC(R1)(R2)又はAr1に結合している、1又は2個の窒素原子を有する置換又は非置換の含窒素複素環基(ここで、前記置換又は非置換の含窒素複素環基は1−ピペラジニル基、1−ピロリジニル基、ピペリジノ基、モルホリノ基、1,1−ジオキシドチオモルホリノ基、ペルヒドロ−1,4−チアジン−4−イル基、1−ピロリル基及び1−ピラゾリル基から選ばれる含窒素複素環基であり、前記含窒素複素環基はC1−5−アルキル基、C1−6−アルコキシ基及びハロゲン原子から選ばれる1つ以上の置換基で置換されていてもよい。)、又は次式(II):
R3、R4、R5及びR6は、それぞれ、水素原子又はメチル基であり;
R12及びR13は、それぞれ、水素原子、又はC1−3−アルキル基であり、前記C1−3−アルキル基はアミノ基、水酸基、カルボキシル基、シアノ基、ハロゲン原子及びニトロ基から選ばれる1以上の置換基で置換されていてもよい。)
で示される基であり;
nは0、1又は2であり;
R1及びR2は、それぞれ、水素原子、C1−3−アルキル基、シアノ基又はカルボキシル基であり、前記C1−3−アルキル基はアミノ基、水酸基、カルボキシル基、シアノ基、ハロゲン原子及びニトロ基から選ばれる1以上の置換基で置換されていてもよく、R1及びR2は、共同してオキソ基を表してもよく、nが2のとき、R1同士又はR2同士は同一でも異なっていてもよい。]
で示される化合物又はその塩を含有する植物成長促進剤。 - 前記式(I)中のR1及びR2が水素原子であり、nが1又は2である請求項1記載の植物成長促進剤。
- 前記式(Ia)中のR1及びR2が水素原子である請求項2記載の植物成長促進剤。
- 前記式(I)又は(Ia)中のAr1が1個のメチレンジオキシ基、又は1もしくは2個のメトキシ基で置換されたフェニル基である請求項1〜4のいずれか1項に記載の植物成長促進剤。
- 前記式(I)中のNZが飽和含窒素複素環基である請求項1及び3〜5のいずれか1項に記載の植物成長促進剤。
- 植物体、植物細胞、植物組織片又は植物種子を、請求項1〜6のいずれか1項に記載の植物成長促進剤と接触させることを含む植物成長促進方法。
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