JP5266055B2 - 殺微生物剤として有用な複素環式アミド誘導体 - Google Patents
殺微生物剤として有用な複素環式アミド誘導体 Download PDFInfo
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- 0 Cc1n[n](*)nc1C Chemical compound Cc1n[n](*)nc1C 0.000 description 4
- SXMXEKNHMYELJQ-DAXSKMNVSA-N C/C=C(/C)\CCNC Chemical compound C/C=C(/C)\CCNC SXMXEKNHMYELJQ-DAXSKMNVSA-N 0.000 description 1
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- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members 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
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- C07C205/12—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by halogen atoms having nitro groups bound to carbon atoms of six-membered aromatic rings the six-membered aromatic ring or a condensed ring system containing that ring being substituted by halogen atoms
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- C07C205/37—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups having nitro groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton to carbon atoms of the same non-condensed six-membered aromatic ring or to carbon atoms of six-membered aromatic rings being part of the same condensed ring system the oxygen atom of at least one of the etherified hydroxy groups being further bound to an acyclic carbon atom
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- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
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- 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
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Description
R1は、水素、C1-4アルキル、C1-4ハロアルキル、C1-4アルコキシ、C1-4ハロアルコキシ、CH2C≡CR9、CH2CR10=CHR11、CH=C=CH2又はCOR12であり;
R2及びR3はそれぞれ、独立に、水素、ハロ、C1-4アルキル、C1-4アルコキシ、C1-4ハロアルキル又はC1-4ハロアルコキシであり;
R4及びR5はそれぞれ、独立に、ハロ、シアノ及びニトロから選択され;あるいはR4及びR5の一方は水素であり、他方はハロ、シアノ及びニトロから選択され;
R6、R7及びR8はそれぞれ、独立に、水素、ハロ、シアノ、ニトロ、C1-4アルキル、C1-4ハロアルキル、C1-4アルコキシ(C1-4)アルキル、C1-4ハロアルコキシ(C1-4)アルキル又はC1-4ハロアルコキシであり、ただしR6、R7及びR8の少なくとも1つは水素ではなく;
R9、R10及びR11はそれぞれ、独立に、水素、ハロ、C1-4アルキル、C1-4ハロアルキル又はC1-4アルコキシ(C1-4)アルキルであり;そして
R12は、水素、C1-6アルキル、C1-6ハロアルキル、C1-4アルコキシ(C1-4)アルキル、C1-4アルキルチオ(C1-4)アルキル、C1-4アルコキシ又はアリールである)の化合物、を供する。
一般式(Het1)のピロール−3−イル及び一般式(Het2)のピラゾール−4−イル:
一般式(Het3)のチアゾール−5−イル及びオキサゾール−5−イル:
一般式(Het4)の1,2,3−トリアゾール−4−イル:
一般式(Het5)のピリド−3−イル:
一般式(Het6)の2,3−ジヒドロ[1,4]オキサチイン−5−イル:
である。
表1〜30は、それぞれ69個の式(I)の化合物を含んで成り、ここで式中R1、R2、R3、R4及びR5は以下の表X中に与えられた意味を有し、そしてHetは以下の関連する表1〜30において与えられた意味を有する。従って、表1はXが1であり、かつHetが表1において与えられた意味を有する場合の表Xに対応し、表2はXが2であり、かつHetが表2において与えられた意味を有する場合の表Xに対応し、そして表3〜30についても同様である。
表31は選択された融点及び選択されたNMRデータを示し、表1〜30の化合物についてほかに言及しない限り溶媒として全てCDCl3を伴う。全てのケースにおいて全ての特性データを挙げる試みは為されていない。
該実施例は、2−メチル−4−トリフルオロメチル−チアゾール−5−カルボン酸(9−ジクロロメチリデン−ベンゾノルボルネン−5−イル)アミド(化合物番号20.01)の調製を説明する。
該実施例は、9−(3−ペンチリデン)−5−ニトロ−ベンゾノルボルナジエン(化合物番号32.01)の調製を説明する:
該実施例は、9−(3−ペンチリデン)−5−ニトロ−ベンゾノルボルネン(化合物番号34.01)の調製を説明する:
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を噴霧容器中の処方した試験化合物(0.02%活性成分)で処理する。適用から1日後、該小麦植物を、該試験植物に胞子懸濁液(1×105の夏胞子/ml)を噴霧することにより接種する。20℃及び95%の相対湿度で2日間のインキュベーション後、該植物をグリーンハウスにて20℃及び60%の相対湿度で8日間維持する。該病害の発生を接種から10日後に評価する。
5週齢のリンゴ苗cv.McIntoshを噴霧容器中の処方した試験化合物(0.02%活性成分)で処理する。適用から1日後、リンゴ植物を、該試験植物上でリンゴウドン粉病に感染させた植物を振盪することにより接種する。14/10時間(明/暗)の照明状況下において22℃及び60%の相対湿度で12日間のインキュベーション後、該病害の発生を評価する。
4週齢のリンゴ苗cv.McIntoshを噴霧容器中の処方した試験化合物(0.02%活性成分)で処理する。適用から1日後、リンゴ植物を、該試験植物に胞子懸濁液(4×105の分生子/ml)を噴霧することにより接種する。21℃及び95%の相対湿度で4日間のインキュベーション後、該植物をグリーンハウス中21℃及び60%の相対湿度に4日間置く。さらに、21℃及び95%の相対湿度における4日間のインキュベーション後、該病害の発生を評価する。
1週齢の大麦植物cv.Reginaを噴霧容器中の処方した試験化合物(0.02%活性成分)で処理する。適用から1日後、該大麦植物を、該試験植物上でウドン粉病に感染させた植物を振盪することにより接種する。グリーンハウスにおいて20℃/18℃(昼/夜)及び60%の相対湿度で6日間のインキュベーション後、該病害の発生を評価する。
5週齢のブドウ苗cv.Gutedelを噴霧容器中の処方した試験化合物(0.02%活性成分)で処理する。適用から2日後、ブドウ植物を、該試験植物に胞子懸濁液(1×106の分生子/ml)を噴霧することにより接種する。グリーンハウスにおいて21℃及び95%の相対湿度で4日間のインキュベーション後、該病害の発生を評価する。
4週齢のトマト植物cv.Roter Gnomを噴霧容器中の処方した試験化合物(0.02%活性成分)で処理する。適用から2日後、トマト植物を、該試験植物に胞子懸濁液(1×105の分生子/ml)を噴霧することにより接種する。育成チャンバーにおいて20℃及び95%の相対湿度で4日間のインキュベーション後、該病害の発生を評価する。
1週齢の小麦植物cv.Arinaを噴霧容器中の処方した試験化合物(0.02%活性成分)で処理する。適用から1日後、該小麦植物を、該試験植物に胞子懸濁液(5×105の分生子/ml)を噴霧することにより接種する。20℃及び95%の相対湿度で1日間のインキュベーション後、該植物を、グリーンハウス中、20℃及び60%の相対湿度で10日間維持する。接種後11日目に該病害の発生を評価する。
1週齢の大麦植物cv.Reginaを噴霧容器中の処方した試験化合物(0.02%活性成分)で処理する。適用から2日後、該大麦植物を、該試験植物に胞子懸濁液(3×104の分生子/ml)を噴霧することにより接種する。グリーンハウス中20℃及び95%の相対湿度で4日間のインキュベーション後、該病害の発生を評価する。
4週齢のトマト植物cv.Roter Gnomを噴霧容器中の処方した試験化合物(0.02%活性成分)で処理する。適用から2日後、該トマト植物を、該試験植物に胞子懸濁液(2.5×105の分生子/ml)を噴霧することにより接種する。育成チャンバー中20℃及び95%の相対湿度で3日間のインキュベーション後、該病害の発生を評価する。
5週齢のブドウ苗cv.Gutedelを噴霧容器中の処方した試験化合物(0.02%活性成分)で処理する。適用から1日後、該ブドウ植物を、該試験植物上でブドウウドン粉病に感染させた植物を振盪することにより接種する。14/10時間(明/暗)の照明状況下において26℃及び60%の相対湿度で7日間のインキュベーション後、該病害の発生を評価する。
処方した試験化合物(0.002%活性成分)を、予め濾紙を備えたポーチに適用する。該適用後、大麦種子(cv.Express)を該濾紙の上層に蒔く。その後、調製したポーチを23℃/18℃(昼/夜)及び80%の相体湿度においてインキュベートする。播種から1週間後、該大麦植物を、該試験植物上でウドン粉病に感染させた植物を振盪することにより接種する。6日間のインキュベーション後、該病害の発生を評価する。各試験化合物の有効性は、全身作用についての指標として使用する。
F・キュルモルム(F. culmorum)の分生子懸濁液(7×105分生子/ml)を処方した試験化合物(0.002%活性成分)と混合する。該混合物を予め濾紙を備えたポーチに適用する。該適用後、小麦種子(cv.Orestis)を該濾紙の上層に蒔く。その後、調製したポーチを、毎日14時間の光を伴い、約10〜18℃及び100%の相体湿度において11日間インキュベートする。根における褐色の病変の形成における病害発生の程度を調べることにより該評価を行う。
所定量のG.グラミニス(G. graminis)の菌糸体を水と混合する。処方した試験化合物(0.002%活性成分)を該菌糸体懸濁液に添加する。該混合物を予め濾紙を備えたポーチに適用する。該適用後、小麦種子(cv.Orestis)を該濾紙の上層に蒔く。その後、調製したポーチを、毎日14時間の光を伴い、18℃/16℃(昼/夜)及び80%の相体湿度において14日間インキュベートする。根の褐変の程度を調べることにより該評価を行う。
処方した試験化合物(0.002%活性成分)を、予め濾紙を備えたポーチに適用する。該適用後、小麦種子(cv.Arina)を該濾紙の上層に蒔く。その後、調製したポーチを23℃/18℃(昼/夜)及び80%の相体湿度においてインキュベートする。播種から1週間後、該小麦植物を、該試験植物に胞子懸濁液(1×105の夏胞子/ml)を噴霧することにより接種する。23℃及び95%の相対湿度において1日間のインキュベーション後、該植物を20℃/18℃(昼/夜)及び80%の相体湿度において9日間維持する。該病害の発生は、接種後10日目に評価する。各試験化合物の有効性は全身活性についての指標として使用する。
所定量のR.ソラニ(R. solani)の菌糸体を水と混合する。処方した試験化合物(0.002%活性成分)を該菌糸体懸濁液に添加する。該混合物を予め濾紙を備えたポーチに適用する。該適用後、稲種子(cv.Koshihikari)を該濾紙の上層に蒔く。その後、調製したポーチを、毎日14時間の光を伴い、23℃/21℃(昼/夜)及び100%の相体湿度において10日間インキュベートする。根における褐色の病変の形成における病害の発生の程度を調べることにより該評価を行う。
処方した試験化合物(0.002%活性成分)を、予め濾紙を備えたポーチに適用する。該適用後、小麦種子(cv.Arina)を該濾紙の上層に蒔く。その後、調製したポーチを23℃/18℃(昼/夜)及び80%の相体湿度においてインキュベートする。播種から1週間後、該小麦植物を、該試験植物に胞子懸濁液(5×105の分生子/ml)を噴霧することにより接種する。23℃及び95%の相対湿度において1日間のインキュベーション後、該植物を20℃/18℃(昼/夜)及び80%の相体湿度において9日間維持する。該病害の発生は、接種後8日目に評価する。各試験化合物の有効性は全身活性についての指標として使用する。
2週齢の小麦植物cv.Ribandを噴霧容器中の処方した試験化合物(0.02%活性成分)で処理する。適用から1日後、該小麦植物を、該試験植物に胞子懸濁液(10×105の分生子/ml)を噴霧することにより接種する。23℃及び95%の相対湿度で1日間のインキュベーション後、該植物を、グリーンハウス中、23℃及び60%の相対湿度で16日間維持する。接種後18日目に該病害の発生を評価する。
Claims (9)
- 式(I)
R1は、水素、C1-4アルキル、C1-4ハロアルキル、C1-4アルコキシ、C1-4ハロアルコキシ、CH2C≡CR9、CH2CR10=CHR11、CH=C=CH2又はCOR12であり;
R2及びR3はそれぞれ、独立に、水素、ハロ、C1-4アルキル、C1-4アルコキシ、C1-4ハロアルキル又はC1-4ハロアルコキシであり;
R4及びR5は共にフルオロ、クロロ、ブロモ、ヨード又はシアノであり;
R6、R7及びR8はそれぞれ、独立に、水素、ハロ、シアノ、ニトロ、C1-4アルキル、C1-4ハロアルキル、C1-4アルコキシ(C1-4)アルキル、C1-4ハロアルコキシ(C1-4)アルキル又はC1-4ハロアルコキシであり、ただしR6、R7及びR8の少なくとも1つは水素ではなく;
R9、R10及びR11はそれぞれ、独立に、水素、ハロ、C1-4アルキル、C1-4ハロアルキル又はC1-4アルコキシ(C1-4)アルキルであり;そして
R12は、水素、C1-6アルキル、C1-6ハロアルキル、C1-4アルコキシ(C1-4)アルキル、C1-4アルキルチオ(C1-4)アルキル、C1-4アルコキシ又はアリールである)の化合物。 - 前記式中、R4及びR5は共にフルオロである、請求項1に記載の式(I)の化合物。
- 前記式中、Hetは、2−C1-4アルキル−4−C1-4ハロアルキルチアゾール−5−イル、2−ハロピリド−3−イル、1−C1-4アルキル−4−C1-4ハロアルキルピロール−3−イル、1−C1-4アルキル−3−C1-4ハロアルキルピラゾール−4−イル又は1−C1-4アルキル−3−C1-4ハロアルキルピラゾール−4−イルであり;R1、R2及びR3は全て水素であり;そしてR4及びR5は共にハロである、請求項1に記載の式(I)の化合物。
- 前記式中、Hetは、2−メチル−4−トリフルオロメチルチアゾール−5−イル、2−クロロピリド−3−イル、1−メチル−4−トリフルオロメチルピロール−3−イル、1−メチル3−トリフルオロメチルピラゾール−4−イル又は1−メチル−3−ジフルオロ−メチルピラゾール−4−イルであり;R1、R2及びR3は全て水素であり;そしてR4及びR5は共にフルオロ、共にクロロ又は共にブロモである、請求項1に記載の式(I)の化合物。
- 植物病原性微生物に対して制御及び保護するための組成物であって、請求項1に記載の式Iの化合物及び不活性担体を含んで成る組成物。
- 植物病原性微生物による有用な植物の感染を制御又は予防する方法であって、ここで請求項1に記載の式Iの化合物又は活性成分として該化合物を含んで成る組成物が、植物、その部分又はその場所に対して適用されることを特徴とする方法。
- 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−(9−ジクロロメチレン−1,2,3,4−テトラヒドロ−1,4−メタノ−ナフタレン−5−イル)−アミドである、請求項1に記載の化合物。
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WO2020141135A1 (en) | 2018-12-31 | 2020-07-09 | Syngenta Crop Protection Ag | Pesticidally active heterocyclic derivatives with sulfur containing substituents |
WO2020164994A1 (en) | 2019-02-13 | 2020-08-20 | Syngenta Crop Protection Ag | Pesticidally active pyrazole derivatives |
WO2020164993A1 (en) | 2019-02-13 | 2020-08-20 | Syngenta Crop Protection Ag | Pesticidally active pyrazole derivatives |
EP3696175A1 (en) | 2019-02-18 | 2020-08-19 | Syngenta Crop Protection AG | Pesticidally active azole-amide compounds |
TW202100015A (zh) | 2019-02-28 | 2021-01-01 | 瑞士商先正達農作物保護公司 | 具有含硫取代基之殺有害生物活性雜環衍生物 |
TW202045011A (zh) | 2019-02-28 | 2020-12-16 | 瑞士商先正達農作物保護公司 | 具有含硫取代基之殺有害生物活性雜環衍生物 |
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CN114617128B (zh) * | 2022-03-28 | 2023-06-16 | 青岛奥迪斯生物科技有限公司 | 一种含喹啉铜的农药组合物及其应用 |
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WO2024077487A1 (en) | 2022-10-11 | 2024-04-18 | Syngenta Crop Protection Ag | Process for the preparation of pyrazole carboxylic acid amides |
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GB0422401D0 (en) | 2004-10-08 | 2004-11-10 | Syngenta Participations Ag | Fungicidal compositions |
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