JP6387000B2 - N−置換スルホキシイミン・ピリジンn−オキシドの製造 - Google Patents
N−置換スルホキシイミン・ピリジンn−オキシドの製造 Download PDFInfo
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- JP6387000B2 JP6387000B2 JP2015520251A JP2015520251A JP6387000B2 JP 6387000 B2 JP6387000 B2 JP 6387000B2 JP 2015520251 A JP2015520251 A JP 2015520251A JP 2015520251 A JP2015520251 A JP 2015520251A JP 6387000 B2 JP6387000 B2 JP 6387000B2
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- 0 *c1ccc(C(CCC2)S2(=N*)=O)cn1 Chemical compound *c1ccc(C(CCC2)S2(=N*)=O)cn1 0.000 description 1
- XYDHWVWJSJZDJQ-XCIOYXGDSA-N CC(/C(/CN)=C/C=C(\C)/C(F)(F)F)S(C)(=NN(O)[I]=O)=O Chemical compound CC(/C(/CN)=C/C=C(\C)/C(F)(F)F)S(C)(=NN(O)[I]=O)=O XYDHWVWJSJZDJQ-XCIOYXGDSA-N 0.000 description 1
- FKNKZJUOKVVKNH-UHFFFAOYSA-N CC(C(C1)=CC=C(C(F)(F)F)N1O)S(C)(=NN(O)[I]=O)=O Chemical compound CC(C(C1)=CC=C(C(F)(F)F)N1O)S(C)(=NN(O)[I]=O)=O FKNKZJUOKVVKNH-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—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
- C07D213/02—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
- C07D213/89—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 with hetero atoms directly attached to the ring nitrogen atom
-
- 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
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
-
- 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
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/80—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2
-
- 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
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
- A01N47/34—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the groups, e.g. biuret; Thio analogues thereof; Urea-aldehyde condensation products
-
- 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
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/40—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having a double or triple bond to nitrogen, e.g. cyanates, cyanamides
-
- 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
- A01N51/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds having the sequences of atoms O—N—S, X—O—S, N—N—S, O—N—N or O-halogen, regardless of the number of bonds each atom has and with no atom of these sequences forming part of a heterocyclic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
Description
ル基は、メチル、エチル、1−メチルエチル、プロピル、1,1−ジメチルエチルおよびシクロプロピルである。用語ハロゲンはフッ素、塩素、臭素およびヨウ素を含む。
XはNO2、CN、COOR4またはCONH2を表し、
Lは単結合を表すかまたはR1、SおよびLが一緒になって、4−、5−もしくは6−員環を表し、
R1は(C1−C4)アルキルを表し、
R2およびR3は個々に水素、メチル、エチル、フルオロ、クロロまたはブロモを表し、
nは0−3からの整数であり、
Yは(C1−C4)ハロアルキル、F、Cl、BrまたはIを表し、そして
R4は(C1−C3)アルキルを表す]
のピリジンN−酸化スルホキシイミン化合物の製法が提供される。
(1)そのXがNO2、CNまたはCONH2である、式(I)の化合物
(2)そのYがCF3またはClである、式(I)の化合物、
(3)そのR2およびR3が独立して水素、メチルまたはエチルを表す、式(I)の化合物、
(4)そのR1がCH3を表し、そしてLが単結合を表す、すなわち構造
をもつ、式(I)の化合物、
(5)そのR1、SおよびLが一緒になって、飽和5−員環を形成し、そしてnが0である、すなわち構造
を含む。
に従う化合物の酸化を含む。
リン酸、トリフルオロ酢酸および硝酸を含む。
dium)ガラス漏斗を通して瀘過し、CH2Cl2(ジクロロメタン)で洗浄した。生成された瀘液を真空下濃縮し、30mLのTHFで希釈し、2回の10mL容量の飽和チオ硫酸ナトリウムで洗浄した。生成された有機相をNa2SO4で乾燥し、瀘過し、真空下濃縮すると、1.33gの黄色の油を与えた。粗物質をアセトンに溶解し、40g RediSepシリカゲルカラム(Isco,Inc.)を備えたTeledyne−Isco
CombiFlash Companion(登録商標)(Isco,Inc.,Lincoln,Nebraska)フラッシュクロマトグラフィーシステムを使用するフラッシュクロマトグラフィーによりクロマトグラフィーにかけた。クロマトグラフィーは40mL/分の流速、280nm(254nmでモニター)における検出、および溶媒として使用されるヘキサンとアセトンを使用して実施した。2分間の75%ヘキサン/25%アセトンで開始し、14分間にわたり100%のアセトンに移行し、次に8分間100%アセトンで維持する直線勾配を使用した。化合物(3)の単離は、以下の特性をもつ75mg(14%収率)の淡褐色の固体を与えた:融点:201−203°C;1H NMR(DMSO−d6)d 8.48(s,1H),8.00(d,1H,J=8.1),7.52(d,1H,J=8.1),4.63(s,2H),3.02(s,3H);MS(ES-)278(M−H).
実施例4〜7の化合物(10)、(11)、(12)および(13)それぞれは下の表Iに示される。化合物(6)、(7)、(8)および(9)(これらも下の表Iに示される)は、化合物(10、(11)、(12)および(13)それぞれを提供するために、実施例1および2に関連して前記のものに類似の方法を使用して酸化された。
実施例8〜9の化合物(14)および(15)はそれぞれ、以下の表IIに示される。化合物(3)および(11)(これも以下の表IIに示される)は実施例3に関して前記のものに類似の方法を使用して酸加水分解されて、化合物(14)および(15)それぞれを提供した。
Claims (10)
- 式(I)
XはNO2、CN、COOR4またはCONH2を表し、
Lは単結合を表すかまたはR1、SおよびLが一緒になって、4−、5−もしくは6−員環を表し、
R1は(C1−C4)アルキルを表し、
R2およびR3は個々に水素、メチル、エチル、フルオロ、クロロまたはブロモを表し、
nは0−3からの整数であり、
Yは(C1−C4)ハロアルキル、F、Cl、BrまたはIを表し、そして
R4は(C1−C3)アルキルを表す]
のN−酸化スルホキシイミン化合物の製法であって、
式(II)
の化合物の酸化を実施する方法を含み、そして該酸化が式(II)の化合物を尿素、過酸化水素および無水トリフルオロ酢酸で処理する方法を含む、製法。 - XがNO2、CNまたはCONH2を表す、請求項1の方法。
- YがCF3またはClを表す、請求項1の方法。
- R2およびR3が独立して、水素、メチルまたはエチルを表す、請求項1の方法。
- XがNO2、CNまたはCONH2,を表し、Yが(C1−C4)ハロアルキルを表し、R2およびR3が個々に水素、メチル、エチル、フルオロ、クロロまたはブロモを表し、そしてnが1−3からの整数である、請求項5の方法。
- XがNO2、CNまたはCONH2を表し、YがCF3を表し、R2およびR3が個々に水素、メチルまたはエチルを表し、そしてnが1−3からの整数である、請求項6の方法。
- 更に、極性溶媒中で酸化を実施する方法を含む、請求項1の方法。
- 極性溶媒がジクロロメタン、テトラヒドロフラン、酢酸エチル、アセトン、ジメチルホルムアミド、アセトニトリルおよびジメチルスルホキシドよりなる群から選択される、請求項9の方法。
Applications Claiming Priority (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US201261666808P | 2012-06-30 | 2012-06-30 | |
US201261666807P | 2012-06-30 | 2012-06-30 | |
US61/666,807 | 2012-06-30 | ||
US61/666,808 | 2012-06-30 | ||
PCT/US2013/045556 WO2014004094A1 (en) | 2012-06-30 | 2013-06-13 | Production of n-substituted sulfoximine pyridine n-oxides |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2015522588A JP2015522588A (ja) | 2015-08-06 |
JP6387000B2 true JP6387000B2 (ja) | 2018-09-05 |
Family
ID=49778790
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2015520251A Active JP6387000B2 (ja) | 2012-06-30 | 2013-06-13 | N−置換スルホキシイミン・ピリジンn−オキシドの製造 |
Country Status (18)
Country | Link |
---|---|
US (1) | US9000180B2 (ja) |
EP (1) | EP2866564B1 (ja) |
JP (1) | JP6387000B2 (ja) |
KR (1) | KR102089479B1 (ja) |
CN (1) | CN104582488A (ja) |
AR (1) | AR092849A1 (ja) |
AU (1) | AU2013280925B2 (ja) |
BR (1) | BR112014033006B8 (ja) |
CA (1) | CA2876192C (ja) |
CO (1) | CO7160112A2 (ja) |
HK (1) | HK1209278A1 (ja) |
IL (1) | IL236478A0 (ja) |
IN (1) | IN2014DN11218A (ja) |
MX (1) | MX352996B (ja) |
NZ (1) | NZ702523A (ja) |
RU (1) | RU2628287C2 (ja) |
WO (1) | WO2014004094A1 (ja) |
ZA (1) | ZA201408994B (ja) |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2014004080A1 (en) * | 2012-06-30 | 2014-01-03 | Dow Agrosciences Llc | Pyridine n-oxides and processes for their preparation |
CN105503672A (zh) * | 2015-12-06 | 2016-04-20 | 杨秀娟 | 一种药物中间体芳基砜类化合物的合成方法 |
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JP2005162732A (ja) * | 2003-11-13 | 2005-06-23 | Bayer Cropscience Ag | 殺虫性ニコチノイルカーバメート類 |
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TW201309635A (zh) * | 2006-02-10 | 2013-03-01 | Dow Agrosciences Llc | 殺蟲性之n-取代(6-鹵烷基吡啶-3-基)烷基磺醯亞胺(二) |
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MX2009000050A (es) * | 2006-08-22 | 2009-01-23 | Basf Se | Amidas picolilicas de acido tiofeno-sulfonico. |
TWI387585B (zh) | 2006-09-01 | 2013-03-01 | Dow Agrosciences Llc | 殺蟲性之n-取代(雜芳基)烷基烴基硫亞胺 |
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-
2013
- 2013-06-13 NZ NZ702523A patent/NZ702523A/en unknown
- 2013-06-13 CA CA2876192A patent/CA2876192C/en active Active
- 2013-06-13 WO PCT/US2013/045556 patent/WO2014004094A1/en active Application Filing
- 2013-06-13 JP JP2015520251A patent/JP6387000B2/ja active Active
- 2013-06-13 IN IN11218DEN2014 patent/IN2014DN11218A/en unknown
- 2013-06-13 CN CN201380044662.2A patent/CN104582488A/zh active Pending
- 2013-06-13 KR KR1020147036274A patent/KR102089479B1/ko active IP Right Grant
- 2013-06-13 AU AU2013280925A patent/AU2013280925B2/en active Active
- 2013-06-13 MX MX2014015696A patent/MX352996B/es active IP Right Grant
- 2013-06-13 EP EP13809642.5A patent/EP2866564B1/en active Active
- 2013-06-13 BR BR112014033006A patent/BR112014033006B8/pt active IP Right Grant
- 2013-06-13 RU RU2015102949A patent/RU2628287C2/ru active
- 2013-06-19 US US13/921,288 patent/US9000180B2/en active Active
- 2013-06-28 AR ARP130102305A patent/AR092849A1/es active IP Right Grant
-
2014
- 2014-12-08 ZA ZA2014/08994A patent/ZA201408994B/en unknown
- 2014-12-25 IL IL236478A patent/IL236478A0/en unknown
- 2014-12-30 CO CO14285923A patent/CO7160112A2/es unknown
-
2015
- 2015-10-13 HK HK15109985.1A patent/HK1209278A1/xx unknown
Also Published As
Publication number | Publication date |
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AU2013280925A1 (en) | 2014-12-18 |
CO7160112A2 (es) | 2015-01-15 |
EP2866564A1 (en) | 2015-05-06 |
IN2014DN11218A (ja) | 2015-10-02 |
US9000180B2 (en) | 2015-04-07 |
AU2013280925B2 (en) | 2016-09-29 |
KR20150032539A (ko) | 2015-03-26 |
BR112014033006B1 (pt) | 2020-03-03 |
CA2876192C (en) | 2021-01-05 |
US20140005406A1 (en) | 2014-01-02 |
WO2014004094A1 (en) | 2014-01-03 |
ZA201408994B (en) | 2016-08-31 |
CA2876192A1 (en) | 2014-01-03 |
EP2866564A4 (en) | 2016-02-24 |
KR102089479B1 (ko) | 2020-03-17 |
RU2015102949A (ru) | 2016-08-20 |
MX352996B (es) | 2017-12-15 |
NZ702523A (en) | 2016-07-29 |
CN104582488A (zh) | 2015-04-29 |
JP2015522588A (ja) | 2015-08-06 |
IL236478A0 (en) | 2015-02-26 |
EP2866564B1 (en) | 2020-02-12 |
BR112014033006A2 (pt) | 2017-06-27 |
RU2628287C2 (ru) | 2017-08-15 |
HK1209278A1 (en) | 2016-04-01 |
BR112014033006B8 (pt) | 2022-10-11 |
AR092849A1 (es) | 2015-05-06 |
MX2014015696A (es) | 2015-08-06 |
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