JP2015120675A - 6−置換ニコチン酸エステル誘導体およびこれを有効成分とする殺菌剤 - Google Patents
6−置換ニコチン酸エステル誘導体およびこれを有効成分とする殺菌剤 Download PDFInfo
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- JP2015120675A JP2015120675A JP2013266945A JP2013266945A JP2015120675A JP 2015120675 A JP2015120675 A JP 2015120675A JP 2013266945 A JP2013266945 A JP 2013266945A JP 2013266945 A JP2013266945 A JP 2013266945A JP 2015120675 A JP2015120675 A JP 2015120675A
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Landscapes
- Pyridine Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
【解決手段】有効成分は、以下の式により表される。
(式中、R1は、C1〜C4のアルキル基、C1〜C4のアルコキシ基、C1〜C4のアルコキシメチル基またはアミノ基を示し、R2は、水素原子、C1〜C4のアルキル基またはアミノ基を示し、R3は、C1〜C4のアルキル基、C1〜C4のアルコキシ基、ベンジルオキシ基または
を示し、R4は、水素原子、ハロゲン原子、C1〜C4のアルキル基またはC1〜C4のアルコキシ基を示し、ただし、R1がC1〜C4のアルキル基を示す場合は、R2は水素原子またはC1〜C4のアルキル基を示す。)
【選択図】なし
Description
(特許文献1)
(特許文献2)
(特許文献3)
(特許文献4、医薬活性)
特許文献5では、以下の化合物(43頁化合物番号1.59)が開示されている。しかしながら、特許文献5は殺虫剤としての用途に関するものであり、当該化合物はピリジン環のエステル基のパラ位に塩素原子を有する。
(特許文献5、殺虫活性)
(特許文献6、殺虫活性)
(特許文献7、除草活性)
(特許文献8、除草活性)
(特許文献9、除草活性)
具体的に述べれば、特許文献10は、以下の化合物を開示している(50頁の化合物番号48)。しかしながら、当該化合物はピリジン環のエステル基のパラ位に塩素原子を有する化合物である。
(特許文献10、殺菌活性)
(特許文献11、殺菌活性)
(特許文献12、医薬活性)
(特許文献13、医薬活性)
(特許文献14、医薬活性)
(特許文献15、医薬活性)
(特許文献16、医薬活性)
(特許文献17、医薬活性)
即ち、本発明は、下式[I]、
[I]
(式中、R1は、C1〜C4のアルキル基、C1〜C4のアルコキシ基、C1〜C4のアルコキシメチル基またはアミノ基を示し、R2は、水素原子、C1〜C4のアルキル基またはアミノ基を示し、R3は、C1〜C4のアルキル基、C1〜C4のアルコキシ基、ベンジルオキシ基または
を示し、R4は、水素原子、ハロゲン原子、C1〜C4のアルキル基またはC1〜C4のアルコキシ基を示し、ただし、R1がC1〜C4のアルキル基を示す場合は、R2は水素原子またはC1〜C4のアルキル基を示す。) で表される6-置換ニコチン酸エステル誘導体 (以下、「本発明の化合物」とも言う)およびこれを有効成分として含有する殺菌剤に関するものである。
式[I]で表される本発明の化合物において、R1、R2、R3およびR4で示されるC1〜C4のアルキル基としては、例えば、メチル基、エチル基、n-プロピル基、イソプロピル基、n-ブチル基、イソブチル基、sec-ブチル基、tert-ブチル基などが挙げられる。R4で示されるハロゲン原子としては、例えば、フッ素原子、塩素原子、臭素原子、ヨウ素原子が挙げられる。R1、R3およびR4で示されるC1〜C4のアルコキシ基としては、例えば、メトキシ基、エトキシ基、n-プロポキシ基、イソプロポキシ基、n-ブトキシ基、イソブトキシ基、sec-ブトキシ基、tert-ブトキシ基などが挙げられる。R1で示されるC1〜C4のアルコキシメチル基は、前記したC1〜C4のアルコキシ基で置換されているメチル基を意味する。
本発明の化合物は、文献未記載の新規化合物であり、例えば、公知の出発化合物から下記反応式に従って製造することができる。
一般式[II]で表されるニコチン酸誘導体と、一般式[III]で表されるアルコール誘導体とを縮合剤及び塩基存在下、不活性溶媒中反応させることにより一般式[I]で表される本発明のニコチン酸エステル誘導体を製造することができる。
ここで、化合物[II]及び[III]は、既に公知の化合物であるか、又は公知化合物から当業者であれば、直ちに合成できる化合物である。
本反応における反応温度は、通常-20℃〜120℃、好ましくは0℃〜40℃の範囲で、反応時間は、通常0.2時間〜24時間、好ましくは1時間〜5時間の範囲で行なわれる。一般式[III]で表されるベンジルアルコール誘導体は、一般式[II]で表されるニコチン酸誘導体に対して通常1〜5倍モル、好ましくは1〜1.5倍モルの範囲で使用される。
本反応は溶媒を使用しても使用しなくても良いが、溶媒を使用する場合には、溶媒としては、本反応を著しく阻害しないものであれば特に制限されることなく各種の溶媒が使用され、そのような溶媒としては、例えば、ジメチルエーテルや、ジエチルエーテル、ジイソプロピルエーテル、ジブチルエーテル、テトラヒドロフラン、ジオキサン等の鎖状又は環状エーテル類;ベンゼン、トルエン、キシレン等の芳香族炭化水素類;塩化メチレン、クロロホルム、四塩化炭素等のハロゲン化炭化水素類;アセトニトリル等のニトリル類;酢酸メチル、酢酸エチル、酢酸ブチル等のエステル類;N,N-ジメチルホルムアミド、N,N-ジメチルアセトアミド、ジメチルスルホキシド、1,3-ジメチル-2-イミダゾリジノン等の極性溶媒を好適に挙げることができ、これらの不活性溶媒は単独で又は2種類以上混合して使用することができる。
反応後、目的化合物は、それを含む反応系から常法により容易に単離することができ、例えば、再結晶化や、カラムクロマトグラフィー等で精製などにより目的化合物を調製することができる。
本反応に使用される一般式[II]で表されるニコチン酸誘導体は、例えば、特開2010-083861号公報(特許文献1)に記載された方法に準じて公知化合物から直ちに合成することができる。
本反応に使用される一般式[III]で表されるアルコール誘導体は、例えば、Journal of Medicinal Chemistry, 43巻, 1826頁(2000) (非特許文献1)に記載された方法に準じて、公知化合物から直ちに合成することができる。
農園芸用殺菌剤における有効成分としての本発明の化合物の含有量は、例えば、0.01〜99.5質量%であり、好ましくは、0.5〜90質量%の範囲から選ばれ、製剤形態、施用方法等の種々の条件により適宜決定すればよいが、例えば、粉剤では、約0.5〜20質量%程度、好ましくは、1〜10質量%、水和剤では、約1〜90質量%程度、好ましくは、10〜80質量%、乳剤では、約1〜90質量%程度、好ましくは、10〜40質量%の有効成分を含有するように製造できる。
6-アミノニコチン酸(0.14g)の塩化メチレン(10ml)溶液に、2-メチルフェノキシベンジルアルコール(0.21g)、1-エチル-3-(3-ジメチルアミノプロピル)カルボジイミド塩酸塩(0.23g)と4-ジメチルアミノピリジン(0.15g)を加え、3時間加熱還流した。室温に冷却後、塩化メチレンで抽出し、水層を更に塩化メチレンで抽出した。有機層を合わせて、無水硫酸ナトリウムで乾燥した。減圧下濃縮し、得られた残渣をシリカゲルカラムクロマトグラフィーで精製することにより、表1に記載の本発明の化合物(No.3)、0.26g、mp78-80℃を得た。その他、同様にして、本発明の化合物を合成した。以下の表1には、製造された本発明の化合物を記載する。
[I]
上記表1において、「mp」欄において付された括弧の番号は、以下の括弧の番号と対応し、それぞれ以下のNMRデータで示される化合物を意味する。
1) 1H-NMR(CDCl3)δppm:2.62(3H,s)、5.35(2H,s)、6.99-7.05(4H,m)、7.12(1H,t)、7.25(1H,t)、7.32-7.38(2H,m)、7.42(2H,d)、8.20(1H,d)、9.13(1H,s)。
2) 1H-NMR(CDCl3)δppm:3.88(3H,s)、5.25(2H,s)、6.02(1H,d)、6.99-7.19(4H,m)、7.11(1H,t)、7.32-7.42(4H,m)、8.03(1H,d)。
3) 1H-NMR(CDCl3)δppm:1.01(6H,d)、2.02-2.15(1H,m)、2.61(3H,s)、3.74(2H,d)、5.31(2H,s)、6.91(2H,d)、7.22(1H,d)、7.38(2H,d)、8.18(1H,d)、9.11(1H,s)。
4) 1H-NMR(CDCl3)δppm:2.12(1H,m)、2.58(3H,s)、2.81(3H,d)、3.75(2H,d)、5.31(2H,s)、6.91(2H,d)、7.00(1H,d)、7.38 (2H,d)、8.11(1H,d)。
5) 1H-NMR(CDCl3)δppm:4.91(2H,s)、5.08(2H,s)、5.16(2H,s)、6.45(1H,d)、6.97(2H,m)、7.28-7.46(7H,m)、8.02(1H,d)、8.74(1H,s)。
本発明の化合物(10部)、キシレン(60部)、N−メチル−2−ピロリドン(20部)及びソルポール3005X(非イオン性界面活性剤とアニオン性界面活性剤の混合物、東邦化学工業株式会社、商品名)(10部)を均一に混合溶解して、乳剤を得た。
本発明の化合物(20部)、ニップシールNS-K(ホワイトカーボン、東ソー・シリカ株式会社、商品名)(20部)、カオリンクレー(カオリナイト、竹原化学工業株式会社、商品名)(50部)、サンエキスP−252(リグニンスルホン酸ナトリウム、日本製紙ケミカル株式会社、商品名)(5部)及びルノックスP-65L(アルキルアリルスルホン酸塩、東邦化学工業株式会社、商品名)(5部)をエアーミルにて均一に混合粉砕して、水和剤を得た。
予め混合しておいたプロピレングリコール(5部)、ソルポール7933(アニオン性界面活性剤、東邦化学工業株式会社、商品名)(5部)、水(50部)に本発明の化合物(20部)を分散させ、スラリー状混合物とし、次にこのスラリー状混合物を、ダイノミル(シンマルエンタープライゼス社)で湿式粉砕した後、予めキサンタンガム(0.2部)を水(19.8部)によく混合分散させたものを添加し、フロアブル剤を得た。
本発明の化合物(20部)、ニューカルゲンFS-26(ジオクチルスルホサクシネートとポリオキシエチレントリスチリルフェニルエーテルの混合物、竹本油脂株式会社、商品名)(5部)、プロピレングリコール(8部)、水(50部)を予め混合しておき、このスラリー状混合物を、ダイノミル(シンマルエンタープライゼス社)で湿式粉砕した。次にキサンタンガム(0.2部)を水(16.8部)によく混合分散させゲル状物を作成し、粉砕したスラリーと十分に混合して、フロアブル剤を得た。
化合物 A (特許文献1に記載の化合物)
播種12日後のきゅうり(品種:相模半白)を試験用に準備した。このきゅうりの葉軸を2cm程度残して子葉部分を切り取った。これとは別に32cm×24cm×4.5cm(たて×よこ×高さ)のプラスチックケースの底部に水で十分に湿らせたペーパータオルを敷き、ペーパータオルの上に足つきの網を置いたものを準備した。この網の上に、上記の切り取った子葉部分を、葉が水平になるように並べた。その子葉の中心部に、キュウリ灰色かび病菌(Botrytis cinerea)の胞子懸濁液(1×106 個/ml)を50 μlずつ滴下した。その後、子葉の上に直径6 mmのペーパーディスクを被せた。これとは別に、上記製剤例1に準じて調製した乳剤を、更に0.02%Tween20脱塩水水溶液で希釈して所定濃度の希釈液を調製した。この希釈液を、ペーパーディスクの上から50μlずつ滴下した。プラスチックケースにフタをして20 ℃条件下に72時間置いた後、病斑直径を測定し下記の式にてキュウリ灰色かび病の防除価を求めた。結果を表2に示す。
Claims (2)
- 請求項1に記載の6-置換ニコチン酸エステル誘導体を有効成分として含有することを特徴とする殺菌剤。
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WO2021063736A1 (en) | 2019-10-02 | 2021-04-08 | Basf Se | Bicyclic pyridine derivatives |
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