JP2009520680A - ピラジンカルボキサミド誘導体及びこれを含有する植物病害防除剤 - Google Patents
ピラジンカルボキサミド誘導体及びこれを含有する植物病害防除剤 Download PDFInfo
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- JP2009520680A JP2009520680A JP2008528269A JP2008528269A JP2009520680A JP 2009520680 A JP2009520680 A JP 2009520680A JP 2008528269 A JP2008528269 A JP 2008528269A JP 2008528269 A JP2008528269 A JP 2008528269A JP 2009520680 A JP2009520680 A JP 2009520680A
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- 229940080817 rotenone Drugs 0.000 description 1
- JUVIOZPCNVVQFO-UHFFFAOYSA-N rotenone Natural products O1C2=C3CC(C(C)=C)OC3=CC=C2C(=O)C2C1COC1=C2C=C(OC)C(OC)=C1 JUVIOZPCNVVQFO-UHFFFAOYSA-N 0.000 description 1
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- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
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- 229920002545 silicone oil Polymers 0.000 description 1
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- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
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- 229910052717 sulfur Inorganic materials 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
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- QYPNKSZPJQQLRK-UHFFFAOYSA-N tebufenozide Chemical compound C1=CC(CC)=CC=C1C(=O)NN(C(C)(C)C)C(=O)C1=CC(C)=CC(C)=C1 QYPNKSZPJQQLRK-UHFFFAOYSA-N 0.000 description 1
- ZZYSLNWGKKDOML-UHFFFAOYSA-N tebufenpyrad Chemical compound CCC1=NN(C)C(C(=O)NCC=2C=CC(=CC=2)C(C)(C)C)=C1Cl ZZYSLNWGKKDOML-UHFFFAOYSA-N 0.000 description 1
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- ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 description 1
- RUPAXCPQAAOIPB-UHFFFAOYSA-N tert-butyl formate Chemical group CC(C)(C)OC=O RUPAXCPQAAOIPB-UHFFFAOYSA-N 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
- UBCKGWBNUIFUST-YHYXMXQVSA-N tetrachlorvinphos Chemical compound COP(=O)(OC)O\C(=C/Cl)C1=CC(Cl)=C(Cl)C=C1Cl UBCKGWBNUIFUST-YHYXMXQVSA-N 0.000 description 1
- LITQZINTSYBKIU-UHFFFAOYSA-F tetracopper;hexahydroxide;sulfate Chemical compound [OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[Cu+2].[Cu+2].[Cu+2].[Cu+2].[O-]S([O-])(=O)=O LITQZINTSYBKIU-UHFFFAOYSA-F 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- NWWZPOKUUAIXIW-FLIBITNWSA-N thiamethoxam Chemical compound [O-][N+](=O)\N=C/1N(C)COCN\1CC1=CN=C(Cl)S1 NWWZPOKUUAIXIW-FLIBITNWSA-N 0.000 description 1
- 125000004305 thiazinyl group Chemical group S1NC(=CC=C1)* 0.000 description 1
- DNVLJEWNNDHELH-UHFFFAOYSA-N thiocyclam Chemical compound CN(C)C1CSSSC1 DNVLJEWNNDHELH-UHFFFAOYSA-N 0.000 description 1
- BAKXBZPQTXCKRR-UHFFFAOYSA-N thiodicarb Chemical compound CSC(C)=NOC(=O)NSNC(=O)ON=C(C)SC BAKXBZPQTXCKRR-UHFFFAOYSA-N 0.000 description 1
- YFNCATAIYKQPOO-UHFFFAOYSA-N thiophanate Chemical compound CCOC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OCC YFNCATAIYKQPOO-UHFFFAOYSA-N 0.000 description 1
- QGHREAKMXXNCOA-UHFFFAOYSA-N thiophanate-methyl Chemical group COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC QGHREAKMXXNCOA-UHFFFAOYSA-N 0.000 description 1
- 239000001585 thymus vulgaris Substances 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-M toluene-4-sulfonate Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-M 0.000 description 1
- 230000014616 translation Effects 0.000 description 1
- NKNFWVNSBIXGLL-UHFFFAOYSA-N triazamate Chemical compound CCOC(=O)CSC1=NC(C(C)(C)C)=NN1C(=O)N(C)C NKNFWVNSBIXGLL-UHFFFAOYSA-N 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- DQJCHOQLCLEDLL-UHFFFAOYSA-N tricyclazole Chemical compound CC1=CC=CC2=C1N1C=NN=C1S2 DQJCHOQLCLEDLL-UHFFFAOYSA-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
- 125000005951 trifluoromethanesulfonyloxy group Chemical group 0.000 description 1
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- JARYYMUOCXVXNK-IMTORBKUSA-N validamycin Chemical compound N([C@H]1C[C@@H]([C@H]([C@H](O)[C@H]1O)O[C@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)O)CO)[C@H]1C=C(CO)[C@H](O)[C@H](O)[C@H]1O JARYYMUOCXVXNK-IMTORBKUSA-N 0.000 description 1
- KZSNJWFQEVHDMF-UHFFFAOYSA-M valinate Chemical compound CC(C)C(N)C([O-])=O KZSNJWFQEVHDMF-UHFFFAOYSA-M 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- IGELFKKMDLGCJO-UHFFFAOYSA-N xenon difluoride Chemical compound F[Xe]F IGELFKKMDLGCJO-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
- C07D241/10—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D241/14—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having 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
- C07D241/24—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/60—1,4-Diazines; Hydrogenated 1,4-diazines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
Abstract
式(I)
{式中、Xはハロゲン原子;又はハロゲン原子により置換されていても良い(C1−C3)アルキル基を示し、Yは水素原子;ハロゲン原子;(C1−C3)アルキル基;又は(C1−C3)アルコキシ基を示し、Rは水素原子;ハロゲン原子;シアノ基;ハロゲン原子により置換されていても良い(C1−C6)アルキル基、(C2−C6)アルケニル基、(C2−C6)アルキニル基、(C1−C6)アルコキシ基、(C2−C6)アルケニルオキシ基、(C2−C6)アルキニルオキシ基、(C1−C6)アルキルチオ基、(C1−C6)アルキルスルフィニル基若しくは(C1−C6)アルキルスルホニル基;(C1−C6)アルコキシカルボニル基;(C1−C6)アルコキシイミノ(C1−C3)アルキル基;トリ(C1−C10)アルキルシリル基;又は置換基Zにより置換されていても良いフェニル基、フェノキシ基、ピリジルオキシ基若しくはピリミジルオキシ基を示し、nは1〜5の整数を示す。}で表されるピラジンカルボキサミド誘導体又はその塩類。
Description
1)一般式(I)
3)Rが水素原子;ハロゲン原子;シアノ基;ハロゲン原子により置換されていても良い(C1−C6)アルキル基;ハロゲン原子により置換されていても良い(C2−C6)アルケニル基;ハロゲン原子により置換されていても良い(C2−C6)アルキニル基;ハロゲン原子により置換されていても良い(C1−C6)アルコキシ基;ハロゲン原子により置換されていても良い(C2−C6)アルケニルオキシ基;ハロゲン原子により置換されていても良い(C2−C6)アルキニルオキシ基;ハロゲン原子により置換されていても良い(C1−C6)アルキルチオ基;ハロゲン原子により置換されていても良い(C1−C6)アルキルスルフィニル基;ハロゲン原子により置換されていても良い(C1−C6)アルキルスルホニル基;又は(C1−C6)アルコキシカルボニル基を示し、nが2〜5の整数である場合、Rは同一又は異なっていても良く、また隣り合う2つのRが一緒になって(C3−C5)アルキレン基;(C2−C4)アルキレンオキシ基;又はハロゲン原子により置換されていても良い(C1−C3)アルキレンジオキシ基である1)又は2)に記載のピラジンカルボキサミド誘導体又はその塩類、
4)Yが水素原子である1)乃至3)のいずれかに記載のピラジンカルボキサミド誘導体又はその塩類、
5)1)乃至4)のいずれかに記載のピラジンカルボキサミド誘導体又はその塩類を有効成分として含有することを特徴とする農園芸用植物病害防除剤、及び
6)1)乃至4)のいずれかに記載のピラジンカルボキサミド誘導体又はその塩類の有効量を対象植物又は土壌に処理することを特徴とする植物の病害防除方法に関する。
Yとして好ましくは水素原子;ハロゲン原子;又はメチル基であり、更に好ましくは水素原子である。
nとして好ましくは1〜3の整数である。
製造方法1
一般式(II−1)で表されるハロゲン化ピラジンカルボン酸誘導体を公知文献(例えば、国際公開第05/115994号パンフレット及びJ.Heterocycl Chem.,34,551(1997)を参照。)記載の方法に準じて、フッ化カリウムの存在下、クロロジフルオロ酢酸メチルと反応させることにより、一般式(II’)で表されるトリフルオロメチルピラジンカルボン酸誘導体を製造することができる。
一般式(II−1)で表されるハロゲン化ピラジンカルボン酸誘導体を公知文献(例えば、J.Chem.Soc.Perkin TransI,1988,921、Chem.Lett.,12,1719(1981)及び米国特許公報第4814480号公報を参照。)記載の方法に準じて、トリフルオロ酢酸塩と反応させることにより、一般式(II’)で表されるトリフルオロメチルピラジンカルボン酸誘導体を製造することができる。
一般式(II−1)で表されるハロゲン化ピラジンカルボン酸誘導体を公知文献(例えば、J.Med.Chem.,27(3),255(1984)、J.Chem.Soc.Chem.Commum.,(1992)1,53及びJ.Chem.Soc.Chem.Commum.,1988,638を参照。)記載の方法に準じて、ハロゲン化トリフルオロメチルと反応させることにより、一般式(II’)で表されるトリフルオロメチルピラジンカルボン酸誘導体を製造することができる。
一般式(II−1)で表されるハロゲン化ピラジンカルボン酸誘導体を公知文献(例えば、Terahedron Letters,Vol.31(23), 3357(1990)を参照。)記載の方法に準じて、マグネシウムと反応させてグリニヤール試薬とし、該グリニヤール試薬を二硫化炭素と反応させた後、フッ化キセノンと反応させることにより、一般式(II’)で表されるトリフルオロメチルピラジンカルボン酸誘導体を製造することができる。
一般式(II−2)で表される2,3−ジハロゲン化ピラジン類を参考製造方法1乃至4に記載の方法により一方のハロゲン原子をトリフルオロメチル基で置換して一般式(II−3)で表されるトリフルオロメチルピラジン類とした後、もう一方のハロゲン原子をHeck反応(例えば、特開昭64−000047号公報、特開平8−157421号公報及び特開平9−151156号公報を参照。)によりカルボン酸又はエステルへと変換させて一般式(II’)で表されるトリフルオロメチルピラジンカルボン酸誘導体を製造することができる。
一般式(II−4)で表される2,3−ピラジンジカルボン酸類を公知文献(例えば、特開昭55−59135号公報及び特開昭55−59136号公報を参照。)記載の方法に準じてフッ素化することにより一般式(II’−1)で表されるトリフルオロメチルピラジンカルボン酸誘導体を製造することができる。
一般式(VI−1)又は(VI−2)で表されるケトエステル類とエチレンジアミンとを公知文献(例えば、J.Org.Chem.,45,161(1980)、J.Org.Chem.,45,163(1980)及びIndian J.Org.Chem.Sect.B,23,850(1984)を参照。)記載の方法に準じて反応させて環化し、次いで酸化することにより一般式(II’)で表されるトリフルオロメチルピラジンカルボン酸誘導体を製造することができる。
参考製造方法9
一般式(II−4)で表される2,3−ピラジンジカルボン酸類を公知文献(例えば、特表2004−528297号公報を参照。)記載の方法に準じて一般式(II−7)で表される酸ハロゲン化物を経て一般式(II−8)で表されるアルデヒドに変換した後、そのホルミル基を公知のフッ素化剤(例えば、J.Org.Chem.,64,7048(1999)を参照。)を用いてフッ素化することにより一般式(II’−2)で表されるジフルオロメチルピラジンカルボン酸誘導体を製造することができる。
本発明の一般式(I)で表されるピラジンカルボキサミド誘導体又はその塩類を有効成分として含有する農園芸用植物病害防除剤は、特に水稲、果樹、野菜、その他作物及び花卉の植物病害防除に適している。
ウイルス病病害の具体的病害としては、タバコモザイク病(Tobacco mosaic virus)等が挙げられる。
即ち、一般式(I)で表されるピラジンカルボキサミド誘導体又はその塩類はこれらを適当な不活性担体に、又は必要に応じて補助剤と一緒に適当な割合に配合して溶解、分離、懸濁、混合、含浸、吸着若しくは付着させて適宜の剤型、例えば、懸濁剤、乳剤、液剤、水和剤、顆粒水和剤、粒剤、粉剤、錠剤、パック剤等に製剤して使用できる。
界面活性剤は、例えば有効成分化合物の乳化、分散、可溶化及び/又は湿潤の目的のために使用することができる。界面活性剤としては、例えば、ポリオキシエチレンアルキルエーテル、ポリオキシエチレンアルキルアリールエーテル、ポリオキシエチレン高級脂肪酸エステル、ポリオキシエチレン樹脂酸エステル、ポリオキシエチレンソルビタンモノラウレート、ポリオキシエチレンソルビタンモノオレエート、アルキルアリールスルホン酸塩、ナフタレンスルホン酸縮合物、リグニンスルホン酸塩、高級アルコール硫酸エステル等が挙げられる。
分散安定化、粘着及び/又は結合助剤は、有効成分化合物の分散安定化を目的として、また粒子成形のための粘着及び/又は結合助剤として使用することができる。分散安定化、粘着及び/又は結合助剤としては、例えば、カゼイン、ゼラチン、澱粉、メチルセルロース、カルボキシメチルセルロース、アラビアゴム、ポリビニルアルコール、松根油、糠油、ベントナイト、リグニンスルホン酸塩等が挙げられる。
消泡剤としては、例えば、シリコーン油等が挙げられる。
防腐剤としては、例えば、1,2−ベンズイソチアゾリン−3−オン、パラクロロメタキシレノール、パラオキシ安息香酸ブチル等が挙げられる。
更に、本発明の農園芸用植物病害防除剤には、必要に応じて機能性展着剤、ピペロニルブトキサイド等の代謝分解阻害剤等の活性増強剤、プロピレングリコール等の凍結防止剤、BHT(ジブチルヒドロキシトルエン)等の酸化防止剤、紫外線吸収剤等その他の添加剤等も加えることができる。
本発明の農園芸用植物病害防除剤は各種病害を防除するためにそのまま、又は水等で適宜希釈し、若しくは懸濁させた形で使用すれば良い。
本発明の農園芸用植物病害防除剤の使用量は種々の因子、例えば、目的、対象病害、作物の生育状況、病害の発生傾向、天候、環境条件、剤型、施用方法、施用場所、施用時期等により変動するが、有効成分化合物として10アール当たり約0.001g〜10kg、好ましくは約0.01g〜1kgの範囲から目的に応じて適宜選択すれば良い。
かかる目的で使用する他の農園芸殺菌剤としては、例えば、硫黄、石灰硫黄合剤、塩基性硫酸銅、イプロベンホス、エディフェンホス、トルクロホス・メチル、チラム、ポリカーバメイト、ジネブ、マンゼブ、マンコゼブ、プロピネブ、チオファネート、チオファネートメチル、ベノミル、イミノクタジン酢酸塩、イミノクタジンアルベシル酸塩、メプロニル、フルトラニル、ペンシクロン、フラメトピル、チフルザミド、メタラキシル、オキサジキシル、カルプロパミド、ジクロフルアニド、フルスルファミド、クロロタロニル、クレソキシム・メチル、フェノキサニル、ヒメキサゾール、エクロメゾール、フルオルイミド、プロシミドン、ビンクロゾリン、イプロジオン、トリアジメホン、ビテルタノール、トリフルミゾール、イプコナゾール、フルコナゾール、プロピコナゾール、ジフェノコナゾール、ミクロブタニル、テトラコナゾール、ヘキサコナゾール、テブコナゾール、チアジニル、イミベンコナゾール、プロクロラズ、ペフラゾエート、シプロコナゾール、イソプロチオラン、フェナリモル、ピリメタニル、メパニピリム、ピリフェノックス、フルアジナム、トリホリン、ジクロメジン、アゾキシストロビン、チアジアジン、キャプタン、プロベナゾール、アシベンゾラルSメチル、フサライド、トリシクラゾール、ピロキロン、キノメチオネート、オキソリニック酸、ジチアノン、カスガマイシン、バリダマイシン、ポリオキシン、ブラストサイジン又はストレプトマイシン等を挙げることができる。
N−(2−ブロモフェニル)−3−メチルピラジン−2−カルボキサミド(0.4g;1.4mmol)及び4−トリフルオロメトキシフェニルボロン酸(0.31g;1.5mmol)のトルエン10mL溶液に炭酸ナトリウム(0.6g;5.7mmol)の水5mL溶液を加え、テトラキス(トリフェニルホスフィン)パラジウム(0)(0.1g;0.09mmol)を添加した。アルゴン気流下、6時間加熱還流した後、室温にまで冷却し酢酸エチルと水を加え分液した。有機層を水及び飽和食塩水で順次洗浄し無水硫酸ナトリウムで乾燥した。減圧下に濃縮した後、残渣をシリカゲルカラムクロマトグラフィ(ヘキサン:酢酸エチル=4:1)で精製して表題化合物(0.35g)を得た。
収率:68%
物性:融点 120〜121℃
4’−クロロビフェニル−2−イルアミン(0.3g;1.5mmol)及び3−トリフルオロメチルピラジン−2−カルボン酸クロリド(0.32g;1.5mmol)のTHF(テトラヒドロフラン)(10mL)溶液にトリエチルアミン(0.2g;2mmol)を加え、室温にて2時間撹拌した。水を加えて反応を停止し、酢酸エチルで抽出した。無水硫酸ナトリウムで乾燥後溶媒を減圧下に濃縮し、残渣をシリカゲルカラムクロマトグラフィ(ヘキサン:酢酸エチル=3:1)で精製して表題化合物(0.47g)を得た。
収率:85%
物性:融点 144〜145℃
尚、製剤例中、部とあるのは質量部を示す。
[製剤例1]
本発明化合物 10部
キシレン 70部
N−メチルピロリドン 10部
ポリオキシエチレンノニルフェニルエーテルと
アルキルベンゼンスルホン酸カルシウムとの混合物 10部
以上を均一に混合溶解して乳剤とする。
本発明化合物 3部
クレー粉末 82部
珪藻土粉末 15部
以上を均一に混合粉砕して粉剤とする。
本発明化合物 5部
ベントナイトとクレーの混合粉末 90部
リグニンスルホン酸カルシウム 5部
以上を均一に混合し、適量の水を加えて混練し、造粒、乾燥して粒剤とする。
本発明化合物 20部
カオリンと合成高分散珪酸 75部
ポリオキシエチレンノニルフェニルエーテルと
アルキルベンゼンスルホン酸カルシウムとの混合物 5部
以上を均一に混合粉砕して水和剤とする。
比較化合物A:3−メチル−N−(2−メチルインダン−4−イル)ピラジン−2−カルボキサミド(特開平2−175号公報に記載の化合物番号13の化合物)
比較化合物B:N−{3−イソブチル−4−[1−メトキシ−2,2,2−トリフルオロ−1−(トリフルオロメチル)エチル]フェニル}−3−トリフルオロメチルピラジン−2−カルボキサミド(国際公開第05/115994号パンフレットに記載の化合物番号1−43の化合物)
比較化合物C:2−クロロ−N−(4’−クロロビフェニル−2−イル)ニコチン酸アミド(日本特許第3202079号公報に記載の化合物番号3−16の化合物)
リンゴ黒星病防除効果試験
ポットで育成したリンゴ苗木(品種:王林)に本発明化合物を製剤例1にしたがって調製した乳剤を水で所定量に希釈して茎葉散布した。散布翌日にPSA培地(蔗糖20g、寒天15g、ジャガイモ200gの煎汁1000mL、pH7)で培養して得られたリンゴ黒星病菌(Venturia inaequalis) の胞子懸濁液を噴霧接種し、20℃多湿条件下で保持した。接種14日後に数(1)に従って防除価(%)を求め、下記の判定基準に従って防除効果を判定した。
0 : 防除価9%以下
1 : 防除価10〜19%
2 : 防除価20〜29%
3 : 防除価30〜39%
4 : 防除価40〜49%
5 : 防除価50〜59%
6 : 防除価60〜69%
7 : 防除価70〜79%
8 : 防除価80〜89%
9 : 防除価90〜99%
10: 防除価100%
キュウリ灰色かび病防除効果試験
直径9cmのポットで育苗した1葉期のキュウリ(品種:四葉)に本発明化合物を製剤例1にしたがって調製した乳剤を水で所定量に希釈して茎葉散布した。散布翌日にPSA培地で培養して得られたキュウリ灰色かび病菌(Botrytis cinerea)の胞子懸濁液を直径6mmのペーパーディスクに含浸させてキュウリ子葉に置床接種し、20℃多湿条件下で保持した。接種7日後に数(2)に従って防除価を求め、試験例1の判定基準に従って防除効果を判定した。
オオムギうどんこ病防除効果試験
直径6cmのポットで育苗した1葉期のオオムギ(品種:関東6号)に本発明化合物を製剤例1にしたがって調製した乳剤を水で所定量に希釈して茎葉散布した。散布翌日にオオムギうどんこ病菌(Blumeria graminis hordei)に罹病したオオムギ葉から得られた胞子を振りかけて接種し、温室内で保持した。接種7日後に試験例1の判定基準に従って防除効果を判定した。
コムギ赤さび病防除効果試験
直径6cmのポットで育苗した1葉期のコムギ(品種:ホクシン)に本発明化合物を製剤例1にしたがって調製した乳剤を水で所定量に希釈して茎葉散布した。散布翌日にコムギ赤さび病菌(Puccinia recondita)に罹病したコムギ葉から得られた胞子懸濁液を噴霧接種し、20℃多湿条件下で保持した。接種7日後に試験例1の判定基準に従って防除効果を判定した。
Claims (6)
- 一般式(I)
- Xが塩素原子;臭素原子;沃素原子;メチル基;フルオロメチル基;ジフルオロメチル基;又はトリフルオロメチル基である請求項1に記載のピラジンカルボキサミド誘導体又はその塩類。
- Rが水素原子;ハロゲン原子;シアノ基;ハロゲン原子により置換されていても良い(C1−C6)アルキル基;ハロゲン原子により置換されていても良い(C2−C6)アルケニル基;ハロゲン原子により置換されていても良い(C2−C6)アルキニル基;ハロゲン原子により置換されていても良い(C1−C6)アルコキシ基;ハロゲン原子により置換されていても良い(C2−C6)アルケニルオキシ基;ハロゲン原子により置換されていても良い(C2−C6)アルキニルオキシ基;ハロゲン原子により置換されていても良い(C1−C6)アルキルチオ基;ハロゲン原子により置換されていても良い(C1−C6)アルキルスルフィニル基;ハロゲン原子により置換されていても良い(C1−C6)アルキルスルホニル基;又は(C1−C6)アルコキシカルボニル基を示し、nが2〜5の整数である場合、Rは同一又は異なっていても良く、また隣り合う2つのRが一緒になって(C3−C5)アルキレン基;(C2−C4)アルキレンオキシ基;又はハロゲン原子により置換されていても良い(C1−C3)アルキレンジオキシ基である請求項1又は2に記載のピラジンカルボキサミド誘導体又はその塩類。
- Yが水素原子である請求項1乃至3のいずれか1項に記載のピラジンカルボキサミド誘導体又はその塩類。
- 請求項1乃至4のいずれか1項に記載のピラジンカルボキサミド誘導体又はその塩類を有効成分として含有することを特徴とする農園芸用植物病害防除剤。
- 請求項1乃至4のいずれか1項に記載のピラジンカルボキサミド誘導体又はその塩類の有効量を対象植物又は土壌に処理することを特徴とする植物の病害防除方法。
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BR112019020756B1 (pt) | 2017-04-05 | 2023-11-28 | Syngenta Participations Ag | Compostos derivados de oxadiazol microbicidas, composição agroquímica compreendendo os mesmos, método para controlar ou prevenir a infestação de plantas úteis por microrganismos fitopatogênicos e uso desses compostos |
BR112019020734B1 (pt) | 2017-04-05 | 2023-12-05 | Syngenta Participations Ag | Compostos derivados de oxadiazol, composição agroquímica, método para controlar ou prevenir a infestação de plantas úteis por microrganismos fitopatogênicos e uso dos referidos compostos |
WO2018185211A1 (en) | 2017-04-06 | 2018-10-11 | Syngenta Participations Ag | Microbiocidal oxadiazole derivatives |
WO2018219773A1 (en) | 2017-06-02 | 2018-12-06 | Syngenta Participations Ag | Fungicidal compositions |
CN109096209B (zh) * | 2017-06-20 | 2022-03-01 | 华中师范大学 | 吡嗪酰胺类化合物及其制备方法和应用以及杀菌剂 |
US20200315176A1 (en) | 2017-06-28 | 2020-10-08 | Syngenta Participations Ag | Fungicidal compositions |
BR112020000456A2 (pt) | 2017-07-11 | 2020-07-21 | Syngenta Participations Ag | derivados oxadiazol microbiocidas |
WO2019011926A1 (en) | 2017-07-11 | 2019-01-17 | Syngenta Participations Ag | MICROBIOCIDE OXADIAZOLE DERIVATIVES |
BR112020000470A2 (pt) | 2017-07-11 | 2020-07-21 | Syngenta Participations Ag | derivados oxadiazol microbiocidas |
WO2019011923A1 (en) | 2017-07-11 | 2019-01-17 | Syngenta Participations Ag | MICROBIOCIDE OXADIAZOLE DERIVATIVES |
WO2019012001A1 (en) | 2017-07-12 | 2019-01-17 | Syngenta Participations Ag | MICROBIOCIDE OXADIAZOLE DERIVATIVES |
WO2019012011A1 (en) | 2017-07-12 | 2019-01-17 | Syngenta Participations Ag | MICROBIOCIDE OXADIAZOLE DERIVATIVES |
BR112020000463A2 (pt) | 2017-07-13 | 2020-07-21 | Syngenta Participations Ag | derivados oxadiazol microbiocidas |
EP3681868B1 (en) | 2017-09-13 | 2021-08-04 | Syngenta Participations AG | Microbiocidal quinoline (thio)carboxamide derivatives |
BR112020004926A2 (pt) | 2017-09-13 | 2020-09-15 | Syngenta Participations Ag | derivados de quinolino(tio)carboxamida microbiocidas |
WO2019053024A1 (en) | 2017-09-13 | 2019-03-21 | Syngenta Participations Ag | MICROBIOCIDE DERIVATIVES OF QUINOLINE (THIO) CARBOXAMIDE |
CN111093372B (zh) | 2017-09-13 | 2022-05-27 | 先正达参股股份有限公司 | 杀微生物的喹啉(硫代)羧酰胺衍生物 |
JP7258859B2 (ja) | 2017-09-13 | 2023-04-17 | シンジェンタ パーティシペーションズ アーゲー | 殺微生物性キノリン(チオ)カルボキサミド誘導体 |
JP7330949B2 (ja) | 2017-09-13 | 2023-08-22 | シンジェンタ パーティシペーションズ アーゲー | 殺微生物性キノリン(チオ)カルボキサミド誘導体 |
JP7150009B2 (ja) | 2017-09-13 | 2022-10-07 | シンジェンタ パーティシペーションズ アーゲー | 殺微生物性キノリン(チオ)カルボキサミド誘導体 |
UY37912A (es) | 2017-10-05 | 2019-05-31 | Syngenta Participations Ag | Derivados de picolinamida fungicidas que portan grupos terminales heteroarilo o heteroariloxi |
UY37913A (es) | 2017-10-05 | 2019-05-31 | Syngenta Participations Ag | Derivados de picolinamida fungicidas que portan un grupo terminal cuaternario |
BR112020009659A2 (pt) | 2017-11-15 | 2020-11-10 | Syngenta Participations Ag | derivados picolinamida microbiocidas |
CN111356679A (zh) | 2017-11-20 | 2020-06-30 | 先正达参股股份有限公司 | 杀微生物的噁二唑衍生物 |
US11882834B2 (en) | 2017-11-29 | 2024-01-30 | Syngenta Participations Ag | Microbiocidal thiazole derivatives |
WO2019121149A1 (en) | 2017-12-19 | 2019-06-27 | Syngenta Participations Ag | Microbiocidal picolinamide derivatives |
WO2019207062A1 (en) | 2018-04-26 | 2019-10-31 | Syngenta Participations Ag | Microbiocidal oxadiazole derivatives |
BR112020026877A2 (pt) | 2018-06-29 | 2021-04-06 | Syngenta Crop Protection Ag | Derivados de oxadiazol microbiocidas |
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WO2020007646A1 (en) | 2018-07-02 | 2020-01-09 | Basf Se | Pesticidal mixtures |
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WO2020070132A1 (en) | 2018-10-06 | 2020-04-09 | Syngenta Participations Ag | Microbiocidal quinoline dihydro-(thiazine)oxazine derivatives |
KR20200040348A (ko) | 2018-10-08 | 2020-04-20 | 한국화학연구원 | 티오펜 카르복사미드계 유도체 및 이를 함유하는 식물 병해 방제제 |
TW202035404A (zh) | 2018-10-24 | 2020-10-01 | 瑞士商先正達農作物保護公司 | 具有含亞碸亞胺的取代基之殺有害生物活性雜環衍生物 |
WO2020141135A1 (en) | 2018-12-31 | 2020-07-09 | Syngenta Crop Protection Ag | Pesticidally active heterocyclic derivatives with sulfur containing substituents |
WO2020141136A1 (en) | 2018-12-31 | 2020-07-09 | Syngenta Crop Protection Ag | Pesticidally active heterocyclic derivatives with sulfur containing substituents |
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WO2007072999A1 (en) | 2007-06-28 |
US20090233934A1 (en) | 2009-09-17 |
KR20080092344A (ko) | 2008-10-15 |
IL191884A0 (en) | 2008-12-29 |
CA2633207A1 (en) | 2007-06-28 |
AR058583A1 (es) | 2008-02-13 |
AU2006328335A1 (en) | 2007-06-28 |
JP5090351B2 (ja) | 2012-12-05 |
KR101271503B1 (ko) | 2013-06-05 |
EP1963286B1 (en) | 2012-02-22 |
IL191884A (en) | 2015-02-26 |
US8168638B2 (en) | 2012-05-01 |
TWI372752B (en) | 2012-09-21 |
ES2380686T3 (es) | 2012-05-17 |
CA2633207C (en) | 2013-11-05 |
BRPI0620444A2 (pt) | 2011-11-08 |
PL1963286T3 (pl) | 2012-07-31 |
TW200728292A (en) | 2007-08-01 |
AU2006328335B2 (en) | 2012-03-22 |
BRPI0620444B1 (pt) | 2020-12-22 |
EP1963286A1 (en) | 2008-09-03 |
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