JP2021530450A - 抗菌剤としての置換チオフェンカルボキサミド類及び類縁体 - Google Patents
抗菌剤としての置換チオフェンカルボキサミド類及び類縁体 Download PDFInfo
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- JP2021530450A JP2021530450A JP2020571825A JP2020571825A JP2021530450A JP 2021530450 A JP2021530450 A JP 2021530450A JP 2020571825 A JP2020571825 A JP 2020571825A JP 2020571825 A JP2020571825 A JP 2020571825A JP 2021530450 A JP2021530450 A JP 2021530450A
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- MSHXTAQSSIEBQS-UHFFFAOYSA-N s-[3-carbamoylsulfanyl-2-(dimethylamino)propyl] carbamothioate;hydron;chloride Chemical compound [Cl-].NC(=O)SCC([NH+](C)C)CSC(N)=O MSHXTAQSSIEBQS-UHFFFAOYSA-N 0.000 description 1
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- UFEIWEXHHOXPGP-UHFFFAOYSA-M sodium;(4,6-dimethoxypyrimidin-2-yl)carbamoyl-[3-(2,2,2-trifluoroethoxy)pyridin-2-yl]sulfonylazanide Chemical compound [Na+].COC1=CC(OC)=NC(NC(=O)[N-]S(=O)(=O)C=2C(=CC=CN=2)OCC(F)(F)F)=N1 UFEIWEXHHOXPGP-UHFFFAOYSA-M 0.000 description 1
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- QGHREAKMXXNCOA-UHFFFAOYSA-N thiophanate-methyl Chemical compound COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC QGHREAKMXXNCOA-UHFFFAOYSA-N 0.000 description 1
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- YIBACQHAKISWLZ-UHFFFAOYSA-N thiophene-2-sulfonohydrazide Chemical compound NNS(=O)(=O)C1=CC=CS1 YIBACQHAKISWLZ-UHFFFAOYSA-N 0.000 description 1
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- WPALTCMYPARVNV-UHFFFAOYSA-N tolfenpyrad Chemical compound CCC1=NN(C)C(C(=O)NCC=2C=CC(OC=3C=CC(C)=CC=3)=CC=2)=C1Cl WPALTCMYPARVNV-UHFFFAOYSA-N 0.000 description 1
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- YWSCPYYRJXKUDB-KAKFPZCNSA-N tralomethrin Chemical compound CC1(C)[C@@H](C(Br)C(Br)(Br)Br)[C@H]1C(=O)O[C@H](C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 YWSCPYYRJXKUDB-KAKFPZCNSA-N 0.000 description 1
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- YMXOXAPKZDWXLY-QWRGUYRKSA-N tribenuron methyl Chemical group COC(=O)[C@H]1CCCC[C@@H]1S(=O)(=O)NC(=O)N(C)C1=NC(C)=NC(OC)=N1 YMXOXAPKZDWXLY-QWRGUYRKSA-N 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-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
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- DQJCHOQLCLEDLL-UHFFFAOYSA-N tricyclazole Chemical compound CC1=CC=CC2=C1N1C=NN=C1S2 DQJCHOQLCLEDLL-UHFFFAOYSA-N 0.000 description 1
- ONCZDRURRATYFI-TVJDWZFNSA-N trifloxystrobin Chemical compound CO\N=C(\C(=O)OC)C1=CC=CC=C1CO\N=C(/C)C1=CC=CC(C(F)(F)F)=C1 ONCZDRURRATYFI-TVJDWZFNSA-N 0.000 description 1
- AZHZOGYUMMIAOF-UHFFFAOYSA-N trifludimoxazin Chemical compound O=C1N(C)C(=S)N(C)C(=O)N1C(C(=C1)F)=CC2=C1OC(F)(F)C(=O)N2CC#C AZHZOGYUMMIAOF-UHFFFAOYSA-N 0.000 description 1
- IMEVJVISCHQJRM-UHFFFAOYSA-N triflusulfuron-methyl Chemical group COC(=O)C1=CC=CC(C)=C1S(=O)(=O)NC(=O)NC1=NC(OCC(F)(F)F)=NC(N(C)C)=N1 IMEVJVISCHQJRM-UHFFFAOYSA-N 0.000 description 1
- 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 description 1
- JLTRXTDYQLMHGR-UHFFFAOYSA-N trimethylaluminium Chemical compound C[Al](C)C JLTRXTDYQLMHGR-UHFFFAOYSA-N 0.000 description 1
- KVEQCVKVIFQSGC-UHFFFAOYSA-N tritosulfuron Chemical compound FC(F)(F)C1=NC(OC)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)C(F)(F)F)=N1 KVEQCVKVIFQSGC-UHFFFAOYSA-N 0.000 description 1
- 229960004418 trolamine Drugs 0.000 description 1
- 238000002211 ultraviolet spectrum Methods 0.000 description 1
- YNWVFADWVLCOPU-MAUPQMMJSA-N uniconazole P Chemical compound C1=NC=NN1/C([C@@H](O)C(C)(C)C)=C/C1=CC=C(Cl)C=C1 YNWVFADWVLCOPU-MAUPQMMJSA-N 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
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- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 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
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur 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
- C07D333/38—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
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Abstract
Description
本明細書で使用される場合、「C1−C6−アルキル」という用語は、1、2、3、4、5又は6個の炭素原子を有する飽和で分岐若しくは直鎖の炭化水素鎖を指す。C1−C6−アルキルの例には、メチル、エチル、プロピル(n−プロピル)、1−メチルエチル(イソ−プロピル)、ブチル(n−ブチル)、1−メチルプロピル(sec−ブチル)、2−メチルプロピル(イソ−ブチル)、1,1−ジメチルエチル(tert−ブチル)、ペンチル、1−メチルブチル、2−メチルブチル、3−メチルブチル、2,2−ジメチルプロピル、1−エチルプロピル、1,1−ジメチルプロピル、1,2−ジメチルプロピル、ヘキシル、1−メチルペンチル、2−メチルペンチル、3−メチルペンチル、4−メチルペンチル、1,1−ジメチルブチル、1,2−ジメチルブチル、1,3−ジメチルブチル、2,2−ジメチルブチル、2,3−ジメチルブチル、3,3−ジメチルブチル、1−エチルブチル、2−エチルブチル、1,1,2−トリメチルプロピル、1,2,2−トリメチルプロピル、1−エチル−1−メチルプロピル及び1−エチル−2−メチルプロピルを含み、これらに限定されるものではない。特に、前記炭化水素鎖は、1、2、3又は4個の炭素原子を有し(「C1−C4−アルキル」)、例えば、メチル、エチル、プロピル、イソ−プロピル、ブチル、sec−ブチル、イソ−ブチル又はtert−ブチルである。
R1、R2及びR3は、塩素原子であり;
R4は、水素原子、2−メチルプロピル、1−メチルプロピル、シクロプロピル、C2−C6−アルケニルによって置換されているシクロプロピル、アラルキル及びヒドロキシルによって置換されているアラルキルからなる群から選択され、そして、R5は水素原子であり;又は
R4及びR5は、それらが連結されている炭素原子と一緒にシクロプロピルを形成し;
R6は、水素原子、C1−C6−アルキル、C1−C6−ハロアルキル、C1−C6−シアノアルキル、C2−C6−アルケニル、C2−C6−アルキニル、C3−C8−シクロアルキル、アリール、アラルキル、−C1−C6−アルキル−Si(C1−C6−アルキル)3及び−C1−C6−アルキル−C3−C8−シクロアルキルからなる群から選択され;
R7は、水素原子又はC1−C6−アルキルである。
R1、R2及びR3は、塩素原子であり;
R4は、水素原子又はイソブチルであり、そして、R5は、水素原子であり;又は
R4及びR5は、それらが連結されている炭素原子と一緒にシクロプロピルを形成し;
R6は、水素原子又はC1−C6−アルキル、好ましくは水素原子又はC1−C4−アルキル、より好ましくは、水素原子、メチル若しくはエチルである。
本発明は、式(II)の化合物の製造方法に関する。式(II)の化合物は、公知の方法(このなかの参考文献参照)に類似の各種経路によって及び下記の本明細書に記載の及び実験の部に記載の下記の合成経路の1以上によって、製造することができる。
別段の断りがない限り、下記において、R1、R2、R3、R4、R5、R6及びR7は、式(II)の化合物について上記で提供のものと同じ意味を有する。
本明細書で定義の式(II)の化合物は、下記の反応図式によって描かれたように、式(XIV)の化合物又はその塩の一つを、式(XV)の化合物又はその塩の一つと反応させる段階を含む方法A2によって製造することができ:
本明細書で定義の式(II)の化合物は、下記の反応図式に描いたように、式(XVII)の化合物又はその塩の一つのジアゾ化を行い、続いて、芳香族置換を行って式(II)の化合物を提供する段階を含む方法C2によって製造することができ:
U13、U14及びU15は、独立に、アミノ基又は塩素原子であり、但し、U13、U14又はU15のうちの一つのみがアミノ基であり、
U16、U17及びU18は、独立に、保護されたアミノ基又は塩素原子であり、但し、U16、U17又はU18のうちの少なくとも一つは、保護されたアミノ基である。
本発明は、式(II)の化合物の製造のための中間体に関する。
R1、R2、R3は、塩素原子であり;
R4は、水素原子、2−メチルプロピル、1−メチルプロピル、シクロプロピル、C2−C6−アルケニルによって置換されているシクロプロピル、アラルキル及びヒドロキシルによって置換されているアラルキルからなる群から選択され、そして、R5は、水素原子であり;又は
R4及びR5は、それらが連結されている炭素原子と一緒にシクロプロピルを形成し;
R6は、水素原子、C1−C6−アルキル、C1−C6−ハロアルキル、C1−C6−シアノアルキル、C2−C6−アルケニル、C2−C6−アルキニル、C3−C8−シクロアルキル、アリール、アラルキル、−C1−C6−アルキル−Si(C1−C6−アルキル)3及び−C1−C6−アルキル−C3−C8−シクロアルキルからなる群から選択される。
R4は、水素原子、2−メチルプロピル、1−メチルプロピル、シクロプロピル、C2−C6−アルケニルによって置換されているシクロプロピル、アラルキル及びヒドロキシルによって置換されているアラルキルからなる群から選択され、そして、R5は、水素原子であり;又は
R4及びR5は、それらが連結されている炭素原子と一緒にシクロプロピルを形成し;
R6は、水素原子、C1−C6−アルキル、C1−C6−ハロアルキル、C1−C6−シアノアルキル、C2−C6−アルケニル、C2−C6−アルキニル、C3−C8−シクロアルキル、アリール、アラルキル、−C1−C6−アルキル−Si(C1−C6−アルキル)3及び−C1−C6−アルキル−C3−C8−シクロアルキルからなる群から選択され;
但し、式(XVIc)の化合物は、
−N−[(4,5−ジクロロ−2−チエニル)カルボニル]グリシン[138326−45−1]、
−N−[(4,5−ジクロロ−2−チエニル)カルボニル]イソロイシン[138326−47−3]、
−N−[(4,5−ジクロロ−2−チエニル)カルボニル]ロイシン[138326−54−2]、
−メチルN−[(4,5−ジクロロ−2−チエニル)カルボニル]ロイシネート[138326−32−6]、
−メチルN−[(4,5−ジクロロ−2−チエニル)カルボニル]イソロイシネート[138326−33−7]、
−2,2,2−トリフルオロエチルN−[(4,5−ジクロロ−2−チエニル)カルボニル]バリネート[138326−35−9]、
−2,2,2−トリフルオロエチルN−[(4,5−ジクロロ−2−チエニル)カルボニル]ロイシネート[138326−36−0]、及び
−2,2,2−トリフルオロエチルN−[(4,5−ジクロロ−2−チエニル)カルボニル]イソロイシネート[138326−37−1]、を表さない。
R1、R2、R3は、塩素原子であり;
R4は、水素原子、2−メチルプロピル、1−メチルプロピル、シクロプロピル、C2−C6−アルケニルによって置換されているシクロプロピル、アラルキル及びヒドロキシルによって置換されているアラルキルからなる群から選択され、そして、R5は、水素原子であり;又は
R4及びR5は、それらが連結されている炭素原子と一緒にシクロプロピルを形成し;
R6は、水素原子、C1−C6−アルキル、C1−C6−ハロアルキル、C1−C6−シアノアルキル、C2−C6−アルケニル、C2−C6−アルキニル、C3−C8−シクロアルキル、アリール、アラルキル、−C1−C6−アルキル−Si(C1−C6−アルキル)3及び−C1−C6−アルキル−C3−C8−シクロアルキルからなる群から選択され;
ここで、R6が水素原子又はC1−C6−アルキルである場合には、R4は、水素原子、2−メチルプロピル、1−メチルプロピル、シクロプロピル、C2−C6−アルケニルによって置換されているシクロプロピル、アラルキル及びヒドロキシルによって置換されているアラルキルからなる群から選択され、そして、R5は水素原子である。
R1、R2、R3は、塩素原子であり;
R4は、水素原子、2−メチルプロピル、1−メチルプロピル、シクロプロピル、C2−C6−アルケニルによって置換されているシクロプロピル、アラルキル及びヒドロキシルによって置換されているアラルキルからなる群から選択され、そして、R5は、水素原子であり;又は
R4及びR5は、それらが連結されている炭素原子と一緒にシクロプロピルを形成し;
R6は、水素原子、C1−C6−アルキル、C1−C6−ハロアルキル、C1−C6−シアノアルキル、C2−C6−アルケニル、C2−C6−アルキニル、C3−C8−シクロアルキル、アリール、アラルキル、−C1−C6−アルキル−Si(C1−C6−アルキル)3及び−C1−C6−アルキル−C3−C8−シクロアルキルからなる群から選択され;
Vは、ベンジル基、4−メトキシベンジル基、アリル基、置換されていない若しくは置換されているC1−C6−アルコキシカルボニル、置換されていない若しくは置換されているベンジルオキシカルボニル、アリルオキシカルボニル、アセチル基又はトリフルオロアセチル基であり;
ここで、R6が水素原子又はC1−C6−アルキルである場合には、R4は、水素原子、2−メチルプロピル、1−メチルプロピル、シクロプロピル、C2−C6−アルケニルによって置換されているシクロプロピル、アラルキル及びヒドロキシルによって置換されているアラルキルからなる群から選択され、そして、R5は水素原子である。
R1、R2、R3は、塩素原子であり;
U1aは、ヒドロキシ基又はC1−C6−アルコキシ基であり、
但し、式(XIXc)の化合物は、
−メチル3−アミノ−4,5−ジクロロチオフェン−2−カルボキシレート[1621488−35−4]を表さない。
R1、R2、R3は、塩素原子であり;
Vは、ベンジル基、4−メトキシベンジル基、アリル基、置換されていない若しくは置換されているC1−C6−アルコキシカルボニル、置換されていない若しくは置換されているベンジルオキシカルボニル、アリルオキシカルボニル、アセチル基又はトリフルオロアセチル基であり;
U1aは、ヒドロキシ基又はC1−C6−アルコキシ基であり、
但し、式(XXc)の化合物は、
−3−アセトアミド−4,5−ジクロロチオフェン−2−カルボン酸[2090448−72−7]、
−メチル3−アセトアミド−4,5−ジクロロチオフェン−2−カルボキシレート[632356−39−9]、及び
−メチル4,5−ジクロロ−3−[(メトキシカルボニル)アミノ]チオフェン−2−カルボキシレート[35707−28−9]を表さない。
本発明はさらに、本明細書において上記で開示の1以上の式(II)の化合物及びそれらのいずれかの混合物を含む、組成物、特にキサントモナス(Xanthomonas)属の細菌によって引き起こされる植物病害を防除するための組成物に関する。
本発明の化合物(類)及び組成物は、殺菌剤、殺細菌剤、殺ダニ剤、殺線虫剤、殺虫剤、除草剤、肥料、成長調節剤、薬害軽減剤及び/又は情報物質のような他の有効成分と混合することができる。これによって、活性スペクトルを拡大することができ、又は抵抗性の発達を防止することができる。公知の殺菌剤、殺虫剤、殺ダニ剤、殺線虫剤及び殺細菌剤の例は、Pesticide Manual、17th editionに開示されている。
N−メチルイミドホルムアミド、(1.081)イプフェントリフルコナゾール(Ipfentrifluconazole)。
1)+(15.059)、(II.01)+(15.060)、(II.01)+(15.061)、(II.01)+(15.062).(II.01)+(15.063).(II.01)+(15.064).(II.01)+(15.065)、(II.01)+15.066)、(II.01)+(15.067)、(II.01)+(15.068)、(II.01)+(15.069)、(II.01)+(15.070)、(II.01)+(15.071)、(II.01)+(15.072)、(II.01)+(15.073)、(II.01)+(15.074)、(II.01)+(15.075)、(II.01)+(15.076)、(II.01)、(II.01)+(15.077)、(II.01)+(15.078)、(II.01)+(15.079)、(II.01)+(15.080)、(II.01)+(15.081)、(II.01)+(15.082)、(II.01)+(15.083)、(II.01)+(15.084)、(II.01)+(15.085)、(II.01)+(15.086)、(II.01)+(15.087)、(II.01)+(15.088)、(II.01)+(15.089)、(II.01)+(15.090)、(II.01)+(15.091)、(II.01)+(15.092)、(II.01)+(15.093)、(II.01)+(15.094)、(II.01)+(15.095)、(II.01)+(15.096)、(II.01)+(15.097)、(II.01)+(15.098)、(II.01)+(15.099)、(II.01)+(15.100)、(II.01)+(15.101)、(II.01)+(15.102)、(II.01)+(15.103)、(II.01)+(15.104)、(II.01)+(15.105)、(II.01)+(15.106)、(II.01)+(15.107)、(II.01)+(15.108)、(II.01)+(15.109)、(II.01)+(15.110)、(II.01)+(15.111)、(II.01)+(15.112)。これらの組み合わせにおいて、第1の成分は、表II.1で定義の式(II)の化合物(例えばII.01)であり、第2の成分は、本明細書で定義の群1〜15で選ばれる殺菌剤である。例えば組み合わせ(II.01)+(1.001)は、表II.1における化合物II.01及びシプロコナゾール(1.001)を含む組み合わせに相当する。
(A1)細菌、例えば、(A1.1)バチルス・サブティリス(Bacillus subtilis)、特に株QST713/AQ713(Bayer CropScience LP,USからSERENADE OPTI又はSERENADE ASOとして入手可能、NRRL寄託番号B21661、米国特許第6,060,051号に記載);(A1.2)バチルス・アミロリクエファシエンス(Bacillus amyroliquefaciens)、特には株D747(Certis,USからDouble Nickel(商標名)として入手可能、寄託番号FERMBP−8234、米国特許第7,094,592号に開示);(A1.3)バチルス・プミルス(Bacillus pumilus)、特に株BUF−33(NRRL寄託番号50185);(A1.4)バチルス・サブティリス(Bacillus subtilis)変種アミロリクエファシエンス(Amyroliquefaciens)株FZB24(Novozymes,USからTaegro(登録商標)として入手可能);(A1.5)パエニバチルス(Paenibacillus)株、寄託番号NRRLB−50972又は寄託番号NRRLB−67129、国際特許公開番号WO2016/154297に記載;及び
(A2)真菌、例えば、(A2.1)アウレオバシジウム・プルランス(Aureobasidium pullulans)、特には株DSM14940の出芽胞子;(A2.2)株DSM14941のアウレオバシジウム・プルランス(Aureobasidium pullulans)出芽胞子;(A2.3)アウレオバシジウム・プルランス(Aureobasidium pullulans)、特には株DSM14940及びDSM14941の出芽胞子の混合物;
(B)下記の群から選択される殺菌剤:
(B1)細菌、例えば、(B1.1)バチルス・サブティリス(Bacillus subtilis)、特には株QST713/AQ713(Bayer CropScience LP,USからSERENADE OPTI又はSERENADE ASOとして入手可能、NRRL寄託番号B21661、米国特許第6,060,051号に記載);(B1.2)バチルス・プミルス(Bacillus pumilus)、特には株QST2808(Bayer CropScience LP,USからSONATA(登録商標)として入手可能、寄託番号NRRLB−30087、米国特許第6,245,551号に記載);(B1.3)バチルス・プミルス(Bacillus pumilus)、特には株GB34(Bayer AG,DEからYield Shield(登録商標)として入手可能);(B1.4)バチルス・プミルス(Bacillus pumilus)、特には株BUF−33(NRRL寄託番号50185);(B1.5)バチルス・アミロリクエファシエンス(Bacillus Amyroliquefaciens)、特には株D747(Certis,USからDouble Nickel(商標名)として入手可能、寄託番号FERMBP−8234、米国特許第7,094,592号に開示);(B1.6)バチルス・サブティリス(Bacillus subtilis)Y1336(Bion−Tec,TaiwanからBIOBAC(登録商標)WPとして入手可能、登録番号4764、5454、5096及び5277下に台湾で生物殺菌剤として登録);(B1.7)バチルス・アミロリクエファシエンス(Bacillus Amyroliquefaciens)株MBI600(BASF SEからSUBTILEXとして入手可能);(B1.8)バチルス・サブティリス(Bacillus subtilis)株GB03(Bayer AG,DEからKodiak(登録商標)として入手可能);(B1.9)バチルス・サブティリス(Bacillus subtilis)変種アミロリクエファシエンス(Amyroliquefaciens)株FZB24(殺菌剤TAEGRO(登録商標)又はTAEGRO(登録商標)ECO(EPA登録番号70127−5)としてNovozymes Biologicals Inc.,Salem,Virginia又はSyngenta Crop Protection,LLC,Greensboro,North Carolinaから入手可能);(B1.10)バチルス・ミコイデス(Bacillus mycoides)、分離株J(Certis USAからBmJ TGAI又はWGとして入手可能);(B1.11)バチルス・リチェニホルミス(Bacillus licheniformis)、特には株SB3086(NovozymesからEcoGuard TM Biofungicide及びGreen Releafとして入手可能);(B1.12)パエニバチルス(Paenibacillus)株、寄託番号NRRLB−50972又は寄託番号NRRLB−67129、国際特許公開番号WO2016/154297に記載。
ベアウベリア・バシアナ(Beauveria bassiana)、特に、株ATCC 74040、レカニシリウム属種(Lecanicillium spp.)、特に、株HRO LEC 12、メタリジウム・アニソプリアエ(Metarhizium anisopliae)、特に、株F52(DSM3884又はATCC90448)、パエシロミセス・フモソロセウス(Paecilomyces fumosoroseus)(現在:イサリア・フモソロセア(Isaria fumosorosea))、特に、株IFPC 200613又は株Apopka 97(受託番号ATCC20874)、及びパエシロミセス・リラシヌス(Paecilomyces lilacinus)、特に、パエシロミセス・リラシヌス(P.lilacinus)株251(AGAL 89/030550)からなる群から選択される真菌類及び酵母類;
リンゴコカクモンハマキ(Adoxophyes orana)顆粒病ウイルス(GV)、コドリンガ(Cydia pomonella)顆粒病ウイルス(GV)、オオタバコガ(Helicoverpa armigera)核多角体病ウイルス(NPV)、シロイチモジヨトウ(Spodoptera exigua)mNPV、ツマジロクサヨトウ(Spodoptera frugiperda)mNPV、及びエジプトヨトウ(Spodoptera littoralis)(African cotton leafworm)NPVからなる群から選択されるウイルス;
アグロバクテリウム属種(Agrobacterium spp.)、アゾリゾビウム・カウリノダンス(Azorhizobium caulinodans)、アゾスピリルム属種(Azospirillum spp.)、アゾトバクテル属種(Azotobacter spp.)、ブラジリゾビウム属種(Bradyrhizobium spp.)、ブルクホルデリア属種(Burkholderia spp.)、特に、ブルクホルデリア・セパシア(Burkholderia cepacia)(以前は、プセウドモナス・セパシア(Pseudomonas cepacia)として知られていた)、ギガスポラ属種(Gigaspora spp.)又はギガスポラ・モノスポルム(Gigaspora monosporum)、グロムス属種(Glomus spp.)、ラッカリア属種(Laccaria spp.)、ラクトバチルス・ブクネリ(Lactobacillus buchneri)、パラグロムス属種(Paraglomus spp.)、ピソリツス・チンクトルス(Pisolithus tinctorus)、プセウドモナス属種(Pseudomonas spp.)、リゾビウム属種(Rhizobium spp.)、特に、リゾビウム・トリホリイ(Rhizobium trifolii)、リゾポゴン属種(Rhizopogon spp.)、スクレロデルマ属種(Scleroderma spp.)、スイルス属種(Suillus spp.)、及びストレプトミセス(Streptomyces spp.)がある。
(2)GABA依存性クロライドチャンネル遮断薬、例えば、シクロジエン有機塩素系、例えば、クロルダン、及び、エンドスルファン;又は、フェニルピラゾール系(フィプロール系)、例えば、エチプロール、及び、フィプロニル;
(3)ナトリウムチャンネル調節剤、例えば、ピレスロイド系、例えば、アクリナトリン、アレスリン、d−シス−トランスアレスリン、d−トランスアレスリン、ビフェントリン、ビオアレスリン、ビオアレスリンs−シクロペンテニル異性体、ビオレスメトリン、シクロプロトリン、シフルトリン、ベータ−シフルトリン、シハロトリン、ラムダ−シハロトリン、ガンマ−シハロトリン、シペルメトリン、アルファ−シペルメトリン、ベータ−シペルメトリン、シータ−シペルメトリン、ゼータ−シペルメトリン、シフェノトリン[(1R)−トランス異性体]、デルタメトリン、エムペントリン[(EZ)−(1R)異性体]、エスフェンバレレート、エトフェンプロックス、フェンプロパトリン、フェンバレレート、フルシトリネート、フルメトリン、タウ−フルバリネート、ハルフェンプロックス、イミプロトリン、カデトリン、モンフルオロトリン、ペルメトリン、フェノトリン[(1R)−トランス異性体]、プラレトリン、ピレトリン類(除虫菊(pyrethrum))、レスメトリン、シラフルオフェン、テフルトリン、テトラメトリン、テトラメトリン[(1R)異性体]、トラロメトリン、及び、トランスフルトリン;又は、DDT;又は、メトキシクロル;
(4)ニコチン性アセチルコリン受容体(nAChR)競争的調節剤、例えば、ネオニコチノイド系、例えば、アセタミプリド、クロチアニジン、ジノテフラン、イミダクロプリド、ニテンピラム、チアクロプリド、及び、チアメトキサム;又は、ニコチン;又は、スルホキサフロル若しくはフルピラジフロン;
(5)ニコチン性アセチルコリン受容体(nAChR)アロステリック調節剤、例えば、スピノシン系、例えば、スピネトラム、及び、スピノサド;
(6)グルタミン酸依存性クロライドチャンネル(GluCl)アロステリック調節剤、例えば、アベルメクチン系/ミルベマイシン系、例えば、アバメクチン、エマメクチン安息香酸塩、レピメクチン、及び、ミルベメクチン;
(7)幼若ホルモン模倣剤、例えば、幼若ホルモン類似体、例えば、ハイドロプレン、キノプレン、及び、メトプレン;又は、フェノキシカルブ;又は、ピリプロキシフェン;
(8)各種非特異的(多部位)阻害剤、例えば、ハロゲン化アルキル系、例えば、臭化メチル、及び、別のハロゲン化アルキル、又はクロロピクリン、又はフッ化スルフリル、又はホウ砂、又は吐酒石、又はメチルイソシアネート発生剤、例えばダゾメット(diazomet)及びメタム;
(9)弦音器官調節剤、例えばピメトロジン又はフロニカミド;
(10)ダニ成長阻害薬、例えば、クロフェンテジン、ヘキシチアゾクス、及び、ジフロビダジン;又は、エトキサゾール;
(11)昆虫腸膜の微生物ディスラプター、例えば、バシルス・ツリンギエンシス・亜種・イスラエレンシス(Bacillus thuringiensis subspecies israelensis)、バシルス・スファエリクス(Bacillus sphaericus)、バシルス・ツリンギエンシス・亜種・アイザワイ(Bacillus thuringiensis subspecies aizawai)、バシルス・ツリンギエンシス・亜種・クルスタキ(Bacillus thuringiensis subspecies kurstaki)、バシルス・ツリンギエンシス・亜種・テネブリオニス(Bacillus thuringiensis subspecies tenebrionis)、及び、Bt植物タンパク質:Cry1Ab、Cry1Ac、Cry1Fa、Cry1A.105、Cry2Ab、Vip3A、mCry3A、Cry3Ab、Cry3Bb、Cry34Ab1/35Ab1;又は
(12)ミトコンドリアATPシンターゼの阻害薬、例えば、ATPディスラプター、例えばジアフェンチウロン;又は、有機スズ化合物、例えば、アゾシクロチン、シヘキサチン、及び、酸化フェンブタスズ;又は、プロパルギット;又は、テトラジホン;
(13)プロトン勾配破壊による酸化的リン酸化の脱共役剤、例えば、クロルフェナピル、DNOC、及び、スルフルラミド;
(14)ニコチン性アセチルコリン受容体チャンネル遮断剤、例えば、ベンスルタップ、カルタップ塩酸塩、チオシラム(thiocylam)、及び、チオスルタップ−ナトリウム;
(15)キチン生合成の阻害薬(タイプ0)、例えば、ビストリフルロン、クロルフルアズロン、ジフルベンズロン、フルシクロクスロン、フルフェノクスロン、ヘキサフルムロン、ルフェヌロン、ノバルロン、ノビフルムロン、テフルベンズロン、及び、トリフルムロン;
(16)キチン生合成の阻害薬(タイプ1)、例えば、ブプロフェジン;
(17)脱皮ディスラプター(特に、双翅目、即ち双翅類の場合)、例えば、シロマジン;
(18)エクジソン受容体作動薬、例えば、クロマフェノジド、ハロフェノジド、メトキシフェノジド、及び、テブフェノジド;
(19)オクトパミン受容体作動薬、例えば、アミトラズ;
(20)ミトコンドリア複合体III電子伝達阻害薬、例えば、ヒドラメチルノン;又は、アセキノシル;又は、フルアクリピリム;
(21)ミトコンドリア複合体I電子伝達阻害薬、例えば、METI殺ダニ剤の群からのもの、例えば、フェナザキン、フェンピロキシメート、ピリミジフェン、ピリダベン、テブフェンピラド、及び、トルフェンピラド;又は、ロテノン(Derris);
(22)電位依存性ナトリウムチャンネル遮断薬、例えば、インドキサカルブ;又は、メタフルミゾン;
(23)アセチルCoAカルボキシラーゼの阻害薬、例えば、テトロン酸誘導体及びテトラミン酸誘導体、例えば、スピロジクロフェン、スピロメシフェン、及び、スピロテトラマト;
(24)ミトコンドリア複合体IV電子伝達阻害薬、例えば、ホスフィン系、例えば、リン化アルミニウム、リン化カルシウム、ホスフィン、及び、リン化亜鉛;又は、シアン化物、例えば、シアン化カルシウム、シアン化カリウム及びシアン化ナトリウム;
(25)ミトコンドリア複合体II電子伝達阻害薬、例えば、β−ケトニトリル誘導体、例えばシエノピラフェン及びシフルメトフェン、並びにカルボキシアニリド類、例えばピフルブミド;
(28)リアノジン受容体調節剤、例えば、ジアミド系、例えば、クロラントラニリプロール、シアントラニルプロール、及び、フルベンジアミド;
さらなる活性化合物、例えば、アフィドピロペン、アフォキソレイナー、アザジラクチン、ベンクロチアズ、ベンゾキシメート、ビフェナゼート、ブロフラニリド、ブロモプロピレート、キノメチオナート、クロロプラレトリン(Chloroprallethrin)、氷晶石(Cryolite)、シクラニリプロール、シクロキサプリド、シハロジアミド(Cyhalodiamide)、ジクロロメゾチアズ、ジコホル、ε−メトフルトリン(epsilon Metofluthrin)、ε−モムフルトリン(epsilon Momfluthrin)、フロメトキン、フルアザインドリジン、フルエンスルホン、フルフェネリム、フルフェノキシストロビン、フルフィプロール、フルヘキサホン(Fluhexafon)、フルオピラム、フルララネル、フルキサメタミド、フフェノジド(Fufenozide)、グアジピル、ヘプタフルトリン、イミダクロチズ、イプロジオン、κ−ビフェントリン、κ−テフルトリン、ロチラネル(Lotilaner)、メペルフルトリン、パイコングディング(Paichongding)、ピリダリル、ピリフルキナゾン、ピリミノストロビン、スピロブジクロフェン(Spirobudiclofen)、テトラメチルフルトリン、テトラニリプロール、テトラクロルアントラニリプロール(Tetrachlorantraniliprole)、チゴラネル(Tigolaner)、チオキサザフェン、チオフルオキシメート(Thiofluoximate)、トリフルメゾピリム(Triflumezopyrim)及び、ヨードメタン;さらには、バシルス・フィルムス(Bacillus firmus)に基づく調製物(I−1582,BioNeem, Votivo)、さらには以下の化合物:1−{2−フルオロ−4−メチル−5−[(2,2,2−トリフルオロエチル)スルフィニル]フェニル}−3−(トリフルオロメチル)−1H−1,2,4−トリアゾール−5−アミン(WO2006/043635から公知)(CAS 885026−50−6)、{1′−[(2E)−3−(4−クロロフェニル)プロパ−2−エン−1−イル]−5−フルオロスピロ[インドール−3,4′−ピペリジン]−1(2H)−イル}(2−クロロピリジン−4−イル)メタノン(WO2003/106457から公知)(CAS 637360−23−7)、2−クロロ−N−[2−{1−[(2E)−3−(4−クロロフェニル)プロパ−2−エン−1−イル]ピペリジン−4−イル}−4−(トリフルオロメチル)フェニル]イソニコチンアミド(WO2006/003494から公知)(CAS 872999−66−1)、3−(4−クロロ−2,6−ジメチルフェニル)−4−ヒドロキシ−8−メトキシ−1,8−ジアザスピロ[4.5]デカ−3−エン−2−オン(WO2010052161から公知)(CAS 1225292−17−0)、3−(4−クロロ−2,6−ジメチルフェニル)−8−メトキシ−2−オキソ−1,8−ジアザスピロ[4.5]デカ−3−エン−4−イルエチルカーボネート(EP2647626から公知)(CAS−1440516−42−6)、4−(ブタ−2−イン−1−イルオキシ)−6−(3,5−ジメチルピペリジン−1−イル)−5−フルオロピリミジン(WO2004/099160から公知)(CAS 792914−58−0)、PF1364(JP2010/018586から公知)(CAS 1204776−60−2)、N−[(2E)−1−[(6−クロロピリジン−3−イル)メチル]ピリジン−2(1H)−イリデン]−2,2,2−トリフルオロアセトアミド(WO2012/029672から公知)(CAS 1363400−41−2)、(3E)−3−[1−[(6−クロロ−3−ピリジル)メチル]−2−ピリジリデン]−1,1,1−トリフルオロプロパン−2−オン(WO2013/144213から公知)(CAS 1461743−15−6)、N−[3−(ベンジルカルバモイル)−4−クロロフェニル]−1−メチル−3−(ペンタフルオロエチル)−4−(トリフルオロメチル)−1H−ピラゾール−5−カルボキサミド(WO2010/051926から公知)(CAS 1226889−14−0)、5−ブロモ−4−クロロ−N−[4−クロロ−2−メチル−6−(メチルカルバモイル)フェニル]−2−(3−クロロ−2−ピリジル)ピラゾール−3−カルボキサミド(CN103232431から公知)(CAS 1449220−44−3)、4−[5−(3,5−ジクロロフェニル)−4,5−ジヒドロ−5−(トリフルオロメチル)−3−イソオキサゾリル]−2−メチル−N−(シス−1−オキシド−3−チエタニル)ベンズアミド、4−[5−(3,5−ジクロロフェニル)−4,5−ジヒドロ−5−(トリフルオロメチル)−3−イソオキサゾリル]−2−メチル−N−(トランス−1−オキシド−3−チエタニル)ベンズアミド及び4−[(5S)−5−(3,5−ジクロロフェニル)−4,5−ジヒドロ−5−(トリフルオロメチル)−3−イソオキサゾリル]−2−メチル−N−(シス−1−オキシド−3−チエタニル)ベンズアミド(WO2013/050317A1から公知)(CAS 1332628−83−7)、N−[3−クロロ−1−(3−ピリジニル)−1H−ピラゾール−4−イル]−N−エチル−3−[(3,3,3−トリフルオロプロピル)スルフィニル]プロパンアミド、(+)−N−[3−クロロ−1−(3−ピリジニル)−1H−ピラゾール−4−イル]−N−エチル−3−[(3,3,3−トリフルオロプロピル)スルフィニル]プロパンアミド及び(−)−N−[3−クロロ−1−(3−ピリジニル)−1H−ピラゾール−4−イル]−N−エチル−3−[(3,3,3−トリフルオロプロピル)スルフィニル]プロパンアミド(WO2013/162715A2、WO2013/162716A2、US2014/0213448A1から公知)(CAS 1477923−37−7)、5−[[(2E)−3−クロロ−2−プロペン−1−イル]アミノ]−1−[2,6−ジクロロ−4−(トリフルオロメチル)フェニル]−4−[(トリフルオロメチル)スルフィニル]−1H−ピラゾール−3−カルボニトリル(CN101337937Aから公知)(CAS 1105672−77−2)、3−ブロモ−N−[4−クロロ−2−メチル−6−[(メチルアミノ)チオキソメチル]フェニル]−1−(3−クロロ−2−ピリジニル)−1H−ピラゾール−5−カルボキサミド、(Liudaibenjiaxuanan、CN103109816Aから公知)(CAS 1232543−85−9);N−[4−クロロ−2−[[(1,1−ジメチルエチル)アミノ]カルボニル]−6−メチルフェニル]−1−(3−クロロ−2−ピリジニル)−3−(フルオロメトキシ)−1H−ピラゾール−5−カルボキサミド(WO2012/034403A1から公知)(CAS 1268277−22−0)、N−[2−(5−アミノ−1,3,4−チアジアゾール−2−イル)−4−クロロ−6−メチルフェニル]−3−ブロモ−1−(3−クロロ−2−ピリジニル)−1H−ピラゾール−5−カルボキサミド(WO2011/085575A1から公知)(CAS 1233882−22−8)、4−[3−[2,6−ジクロロ−4−[(3,3−ジクロロ−2−プロペン−1−イル)オキシ]フェノキシ]プロポキシ]−2−メトキシ−6−(トリフルオロメチル)ピリミジン(CN101337940Aから公知)(CAS 1108184−52−6);(2E)−及び2(Z)−2−[2−(4−シアノフェニル)−1−[3−(トリフルオロメチル)フェニル]エチリデン]−N−[4−(ジフルオロメトキシ)フェニル]ヒドラジンカルボキサミド(CN101715774Aから公知)(CAS 1232543−85−9);3−(2,2−ジクロロエテニル)−2,2−ジメチル−4−(1H−ベンゾイミダゾール−2−イル)フェニル−シクロプロパンカルボン酸エステル(CN103524422Aから公知)(CAS 1542271−46−4);(4aS)−7−クロロ−2,5−ジヒドロ−2−[[(メトキシカルボニル)[4−[(トリフルオロメチル)チオ]フェニル]アミノ]カルボニル]インデノ[1,2−e][1,3,4]オキサジアジン−4a(3H)−カルボン酸メチルエステル(CN102391261Aから公知)(CAS 1370358−69−2);6−デオキシ−3−O−エチル−2,4−ジ−O−メチル−1−[N−[4−[1−[4−(1,1,2,2,2−ペンタフルオロエトキシ)フェニル]−1H−1,2,4−トリアゾール−3−イル]フェニル]カーバメート]−α−L−マンノピラノース(US2014/0275503A1から公知)(CAS 1181213−14−8);8−(2−シクロプロピルメトキシ−4−トリフルオロメチル−フェノキシ)−3−(6−トリフルオロメチル−ピリダジン−3−イル)−3−アザ−ビシクロ[3.2.1]オクタン(CAS 1253850−56−4)、(8−アンチ)−8−(2−シクロプロピルメトキシ−4−トリフルオロメチル−フェノキシ)−3−(6−トリフルオロメチル−ピリダジン−3−イル)−3−アザ−ビシクロ[3.2.1]オクタン(CAS 933798−27−7)、(8−シン)−8−(2−シクロプロピルメトキシ−4−トリフルオロメチルフェノキシ)−3−(6−トリフルオロメチルピリダジン−3−イル)−3−アザビシクロ[3.2.1]オクタン(WO2007040280A1、WO2007040282A1から公知)(CAS 934001−66−8)及びN−[3−クロロ−1−(3−ピリジニル)−1H−ピラゾール−4−イル]−N−エチル−3−[(3,3,3−トリフルオロプロピル)チオ]プロパンアミド(WO2015/058021A1、WO2015/058028A1から公知)(CAS 1477919−27−9)及びN−[4−(アミノチオキソメチル)−2−メチル−6−[(メチルアミノ)カルボニル]フェニル]−3−ブロモ−1−(3−クロロ−2−ピリジニル)−1H−ピラゾール−5−カルボキサミド(CN103265527Aから公知)(CAS1452877−50−7)、5−(1,3−ジオキサン−2−イル)−4−[[4−(トリフルオロメチル)フェニル]メトキシ]−ピリミジン(WO2013/115391A1から公知)(CAS1449021−97−9)、3−(4−クロロ−2,6−ジメチルフェニル)−4−ヒドロキシ−8−メトキシ−1−メチル−1,8−ジアザスピロ[4.5]デカ−3−エン−2−オン(WO2010/066780A1、WO2011/151146A1から公知)(CAS1229023−34−0)、3−(4−クロロ−2,6−ジメチルフェニル)−8−メトキシ−1−メチル−1,8−ジアザスピロ[4.5]デカン−2,4−ジオン(WO2014/187846A1から公知)(CAS1638765−58−8)、3−(4−クロロ−2,6−ジメチルフェニル)−8−メトキシ−1−メチル−2−オキソ−1,8−ジアザスピロ[4.5]デカ−3−エン−4−イル−炭酸エチルエステル(WO2010/066780A1、WO2011151146A1から公知)(CAS1229023−00−0)、N−[1−[(6−クロロ−3−ピリジニル)メチル]−2(1H)−ピリジニリデン]−2,2,2−トリフルオロ−アセトアミド(DE3639877A1、WO2012029672A1から公知)(CAS1363400−41−2)、[N(E)]−N−[1−[(6−クロロ−3−ピリジニル)メチル]−2(1H)−ピリジニリデン]−2,2,2−トリフルオロ−アセトアミド(WO2016005276A1から公知)(CAS1689566−03−7)、[N(Z)]−N−[1−[(6−クロロ−3−ピリジニル)メチル]−2(1H)−ピリジニリデン]−2,2,2−トリフルオロ−アセトアミド、(CAS1702305−40−5)、3−エンド−3−[2−プロポキ
シ−4−(トリフルオロメチル)フェノキシ]−9−[[5−(トリフルオロメチル)−2−ピリジニル]オキシ]−9−アザビシクロ[3.3.1]ノナン(WO2011/105506A1、WO2016/133011A1から公知)(CAS1332838−17−1)。
アシベンゾラル、アシベンゾラル−S−メチル、5−アミノレブリン酸、アンシミドール、6−ベンジルアミノプリン、ブラシノリド、カテキン、クロロメクワットクロライド、クロプロップ、シクラニリド、3−(シクロプロプ−1−エンイル)プロピオン酸、ダミノジド、ダゾメット、n−デカノール、ジケグラック、ジケグラック−ナトリウム、エンドタール、エンドタール−二カリウム、−二ナトリウム及び−モノ(N,N−ジメチルアルキルアンモニウム)、エテホン、フルメトラリン、フルレノール、フルレノール−ブチル、フルルプリミドール、ホルクロルフェニュロン、ジベレリン酸、イナベンフィド、インドール−3−酢酸(IAA)、4−インドール−3−イル酪酸、イソプロチオラン、プロベナゾール、ジャスモン酸、マレイン酸ヒドラジド、メピコートクロライド、1−メチルシクロプロペン、ジャスモン酸メチル、2−(1−ナフチル)アセトアミド、1−ナフチル酢酸、2−ナフチルオキシ酢酸、ニトロフェノレート混合物、パクロブトラゾール、N−(2−フェニルエチル)−β−アラニン、N−フェニルフタルアミド酸、プロヘキサジオン、プロヘキサジオン−カルシウム、プロヒドロジャスモン、サリチル酸、ストリゴラクトン、テクナゼン、チジアズロン、トリアコンタノール、トリネキサパック、トリネキサパック−エチル、チトデフ(tsitodef)、ウニコナゾール、ウニコナゾール−P。
本発明の化合物(類)及び組成物は、強力な植物防御調節能力を有する。それらは、望ましくない細菌、特にキサントモナス(Xanthomonas)属の細菌を防除するのに用いることができる。本発明の化合物(類)及び組成物を、種子、発芽種子、出芽苗、植物、植物部分、果実,収穫物及び/又は植物が成長する土壌を保護するのに用いることができる。
本発明の化合物(類)及び組成物は、あらゆる植物又は植物部分に適用することができる。
遺伝子組み換え植物(GMO又はトランスジェニック植物)は、異種遺伝子がゲノムに安定に組み込まれている植物である。「異種遺伝子」という表現は、本質的に、植物外で提供又はアセンブルされる遺伝子であり、核に導入された場合は、葉緑体ゲノム又はミトコンドリアゲノムを意味する。この遺伝子は、対象となるタンパク質若しくはポリペプチドを発現することで、又はその植物に存在する他の遺伝子を低下又はサイレンシングすることにより(例えば、アンチセンス技術、共抑制技術、RNA干渉−RNAi−技術又はマイクロRNA−miRNA−技術を用いる)、新たな若しくは改善された農学的その他の特性を形質転換植物に与える。ゲノム中に存在する異種遺伝子は、同様にトランス遺伝子と呼ばれる。植物のゲノム中でのそれの特定の位置によって定義されるトランス遺伝子は、形質転換またはトランスジェニック事象と呼ばれる。
式(II)の化合物の合成
製造例1:メチルN−[(3,4,5−トリクロロ−2−チエニル)カルボニル]グリシネート(化合物II.01)の製造
テトラヒドロフラン4.2mLに溶かした3,4,5−トリクロロチオフェン−2−カルボン酸250mg(1.08mmol)及びエチルグリシネート塩酸塩(1:1)210mg(1.67mmol)の溶液に、トリエチルアミン0.23mL(1.62mmol)を加え、続いて、酢酸エチル中の50重量%プロパンホスホン酸無水物の溶液1.0mL(1.68mmol)を加えた。反応混合物を室温で20時間攪拌した。反応混合物を水で反応停止し、酢酸エチルで抽出した。合わせた有機層を硫酸マグネシウムで脱水し、濾過し、減圧下に濃縮した。残留物をシリカゲルでのカラムクロマトグラフィー(n−ヘプタン/酢酸エチル勾配)によって精製して、メチルN−[(3,4,5−トリクロロ−2−チエニル)カルボニル]グリシネート178mg(純度93%、収率51%)を白色固体として得た。LogP=2.8。(M+H)=302。
テトラヒドロフラン3mLに溶かしたメチルN−[(3,4,5−トリクロロ−2−チエニル)カルボニル]グリシネート178mg(0.59mmol)の溶液に、1M水酸化リチウム水溶液1.3mL(1.3mmol)を滴下した。反応液を室温で4時間攪拌した。反応混合物を、酢酸エチル、水及び飽和重炭酸ナトリウム水溶液で希釈した。有機層を飽和重炭酸ナトリウム水溶液で2回洗浄した。合わせた水層を、0℃で37重量%塩酸水溶液で注意深く酸性とし、酢酸エチルで抽出した。合わせた有機層を硫酸マグネシウムで脱水し、濾過し、減圧下に濃縮して、N−[(3,4,5−トリクロロ−2−チエニル)カルボニル]グリシン159mg(純度98%、収率92%)を白色固体として得た。LogP=2.14。(M−H)=286。
段階1:エチル1−{[(3−アミノ−4,5−ジクロロ−2−チエニル)カルボニル]アミノ}シクロプロパンカルボキシレート(化合物XVIIc.01)の製造
ジクロロメタン4.0mLに溶かした3−アミノ−4,5−ジクロロチオフェン−2−カルボン酸塩酸塩(1:1)(化合物XIXc.01)150mg(0.60mmol)及びエチル1−アミノシクロプロパンカルボキシレート塩酸塩(1:1)255mg(1.50mmol)の溶液に、N,N−ジイソプロピルエチルアミン0.45mL(2.59mmol)と次に2−クロロ−1,3−ジメチルイミダゾリニウムクロライド255mg(1.50mmol)のジクロロメタン(2.0mL)中溶液を加えた。反応混合物を室温で16時間攪拌した。反応混合物を水で反応停止し、ジクロロメタンで抽出した。合わせた有機層を硫酸マグネシウムで脱水し、濾過し、減圧下に濃縮した。残留物を、分取高速液体クロマトグラフィー(アセトニトリル/ギ酸水溶液(1%)勾配)によって精製して、エチル1−{[(3−アミノ−4,5−ジクロロ−2−チエニル)カルボニル]アミノ}シクロプロパンカルボキシレート69mg(純度100%、収率35%)を白色固体として得た。LogP=2.77。(M+H)=323。
塩化銅(I)(9.8mg、0.10mmol)の無水アセトニトリル(0.5mL)中溶液に、0℃で亜硝酸tert−ブチル(13μL、0.10mmol)を滴下した。反応混合物を昇温させて室温としてから、エチル1−{[(3−アミノ−4,5−ジクロロ−2−チエニル)カルボニル]アミノ}シクロプロパンカルボキシレート25mg(0.06mmol)の無水アセトニトリル(0.5mL)中溶液を滴下した。反応混合物を室温で3時間攪拌した。反応混合物をジクロロメタンで希釈し、1M塩酸水溶液で注意深く酸性とした。水層をジクロロメタンで2回抽出した。合わせた有機層を硫酸マグネシウムで脱水し、濾過し、減圧下に濃縮した。残留物を分取高速液体クロマトグラフィー(アセトニトリル/ギ酸水溶液(1%)勾配)によって精製して、エチル1−{[(3,4,5−トリクロロ−2−チエニル)カルボニル]アミノ}シクロプロパンカルボキシレート12mg(純度93%、収率48%)をベージュ固体として得た。LogP=3.40。(M)=341。
表II.1、II.2、II.3、II.4及びII.5に示した本発明による化合物を、上記で提供の実施例と同様にして及び/又は本明細書で開示の方法の一般的説明に従って、製造した。それらの例示的化合物は、異なって指定されていない限りはラセミ体である。
表Aに、上記の表で開示のいくつかの化合物のNMRデータ(1H)を提供している。
δ1(強度1);δ2(強度2);...;δi(強度i);...、δn(強度n)を有する。
実施例A:キサントモナス・カンペストリスpv.カンペストリス(Xanthomonas campestris pv.campestris)イン・ビトロ細胞試験
溶媒:DMSO
培地:LB肉汁培地(Luria Broth Miller) Sigma
接種物:細菌懸濁液
被験化合物を、アセトン/ジメチルスルホキシド/tween(登録商標)の混合物中での均質化によって調製し、水で希釈して所望の濃度を得た。
化合物CMP1及びCMP2の試験を、実施例Bに記載のものと同じ条件で、キサントモナス・カンペストリスpv.カンペストリス(Xanthomonas campestris pv.campestris)(キャベツでの黒斑病)に対するイン・ビボ予防試験で試験した。
PR1(病原性関連タンパク質I)遺伝子(AT2G14610)のサリチル酸応答性プロモーター配列に連結された緑色蛍光タンパク質(GFP)のコード配列を含むシロイヌナズナ(Arabidopsis thaliana)レポーター植物を5日間成長させ、化合物を噴霧した。噴霧後第3日に、Leica Microsystems(Wetzlar、ドイツ)からのMacroFluo装置によって、植物蛍光を評価した。Meta−Morph Microscopy Automation&Image Analysis Software(Molecular Devices,Sunnyvale,Calif.,United States)を用いて、蛍光を定量した。
Claims (13)
- 下記式(II)の化合物。
R1、R2及びR3は、塩素原子であり;
R4は、水素原子、2−メチルプロピル、1−メチルプロピル、シクロプロピル、C2−C6−アルケニルによって置換されているシクロプロピル、アラルキル及びヒドロキシルによって置換されているアラルキルからなる群から選択され、そして、R5は、水素原子であり;又は
R4及びR5は、それらが連結されている炭素原子と一緒にシクロプロピルを形成し;
R6は、水素原子、C1−C6−アルキル、C1−C6−ハロアルキル、C1−C6−シアノアルキル、C2−C6−アルケニル、C2−C6−アルキニル、C3−C8−シクロアルキル、アリール、アラルキル、−C1−C6−アルキル−Si(C1−C6−アルキル)3及び−C1−C6−アルキル−C3−C8−シクロアルキルからなる群から選択され;
R7は、水素原子又はC1−C6−アルキルである。] - R6が、水素原子、C1−C6−アルキル、C1−C6−ハロアルキル、C1−C6−シアノアルキル、C2−C6−アルケニル、C2−C6−アルキニル、シクロプロピル、フェニル、ベンジル、−C1−C6−アルキル−Si(C1−C6−アルキル)3及び−C1−C6−アルキル−シクロプロピルからなる群から選択される、請求項1に記載の式(II)の化合物。
- R7が、水素原子又はメチルである、請求項1又は2に記載の式(II)の化合物。
- R4が、水素原子又はイソブチルである、請求項1〜3のいずれか1項に記載の式(II)の化合物。
- R4及びR5が、それらが連結されている炭素原子と一緒にシクロプロピルを形成している、請求項1、2又は3に記載の式(II)の化合物。
- 少なくとも一つの請求項1〜5のいずれか1項に記載の式(II)の化合物及び少なくとも一つの農業的に好適な補助剤を含む組成物。
- 少なくとも一つの請求項1〜5のいずれか1項に記載の式(II)の化合物又は請求項6に記載の組成物を、植物、植物部分、種子、果実に、又はその植物が成長する土壌に施用する段階を含む、細菌性病害の防除方法。
- 下記式(XVIa)又は(XVIb)の化合物。
R1、R2、R3は、塩素原子であり;
R4は、水素原子、2−メチルプロピル、1−メチルプロピル、シクロプロピル、C2−C6−アルケニルによって置換されているシクロプロピル、アラルキル及びヒドロキシルによって置換されているアラルキルからなる群から選択され、そして、R5は水素原子であり;又は
R4及びR5は、それらが連結されている炭素原子と一緒にシクロプロピルを形成し;
R6は、水素原子、C1−C6−アルキル、C1−C6−ハロアルキル、C1−C6−シアノアルキル、C2−C6−アルケニル、C2−C6−アルキニル、C3−C8−シクロアルキル、アリール、アラルキル、−C1−C6−アルキル−Si(C1−C6−アルキル)3及び−C1−C6−アルキル−C3−C8−シクロアルキルからなる群から選択される。] - 下記式(XVIc)の化合物。
R1、R2、R3は、塩素原子であり;
R4は、水素原子、2−メチルプロピル、1−メチルプロピル、シクロプロピル、C2−C6−アルケニルによって置換されているシクロプロピル、アラルキル及びヒドロキシルによって置換されているアラルキルからなる群から選択され、そして、R5は水素原子であり;又は
R4及びR5は、それらが連結されている炭素原子と一緒にシクロプロピルを形成し;
R6は、水素原子、C1−C6−アルキル、C1−C6−ハロアルキル、C1−C6−シアノアルキル、C2−C6−アルケニル、C2−C6−アルキニル、C3−C8−シクロアルキル、アリール、アラルキル、−C1−C6−アルキル−Si(C1−C6−アルキル)3及び−C1−C6−アルキル−C3−C8−シクロアルキルからなる群から選択され;
但し、式(XVIc)の化合物は、
−N−[(4,5−ジクロロ−2−チエニル)カルボニル]グリシン[138326−45−1]、
−N−[(4,5−ジクロロ−2−チエニル)カルボニル]イソロイシン[138326−47−3]、
−N−[(4,5−ジクロロ−2−チエニル)カルボニル]ロイシン[138326−54−2]、
−メチルN−[(4,5−ジクロロ−2−チエニル)カルボニル]ロイシネート[138326−32−6]、
−メチルN−[(4,5−ジクロロ−2−チエニル)カルボニル]イソロイシネート[138326−33−7]、
−2,2,2−トリフルオロエチルN−[(4,5−ジクロロ−2−チエニル)カルボニル]バリネート[138326−35−9]、
−2,2,2−トリフルオロエチルN−[(4,5−ジクロロ−2−チエニル)カルボニル]ロイシネート[138326−36−0]、及び
−2,2,2−トリフルオロエチルN−[(4,5−ジクロロ−2−チエニル)カルボニル]イソロイシネート[138326−37−1]を表さない。] - 下記式(XVIIa)、(XVIIb)又は(XVIIc)の化合物。
R1、R2、R3は、塩素原子であり;
R4は、水素原子、2−メチルプロピル、1−メチルプロピル、シクロプロピル、C2−C6−アルケニルによって置換されているシクロプロピル、アラルキル及びヒドロキシルによって置換されているアラルキルからなる群から選択され、そして、R5は水素原子であり;又は
R4及びR5は、それらが連結されている炭素原子と一緒にシクロプロピルを形成し;
R6は、水素原子、C1−C6−アルキル、C1−C6−ハロアルキル、C1−C6−シアノアルキル、C2−C6−アルケニル、C2−C6−アルキニル、C3−C8−シクロアルキル、アリール、アラルキル、−C1−C6−アルキル−Si(C1−C6−アルキル)3及び−C1−C6−アルキル−C3−C8−シクロアルキルからなる群から選択され;
ここで、R6が水素原子又はC1−C6−アルキルである場合には、R4は、水素原子、C1−C6−アルキル、アラルキル、ヒドロキシルによって置換されているアラルキル、C1−C6−アルキルスルファニルによって置換されているC1−C6−アルキルからなる群から選択され、そして、R5は水素原子である。]
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