JP2019089711A - Oxadiazole compound and application thereof - Google Patents

Oxadiazole compound and application thereof Download PDF

Info

Publication number
JP2019089711A
JP2019089711A JP2016239161A JP2016239161A JP2019089711A JP 2019089711 A JP2019089711 A JP 2019089711A JP 2016239161 A JP2016239161 A JP 2016239161A JP 2016239161 A JP2016239161 A JP 2016239161A JP 2019089711 A JP2019089711 A JP 2019089711A
Authority
JP
Japan
Prior art keywords
group
substituents selected
compound
optionally
ring
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Pending
Application number
JP2016239161A
Other languages
Japanese (ja)
Inventor
貞幸 有森
Sadayuki Arimori
貞幸 有森
将起 山本
Masaki Yamamoto
将起 山本
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Sumitomo Chemical Co Ltd
Original Assignee
Sumitomo Chemical Co Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Sumitomo Chemical Co Ltd filed Critical Sumitomo Chemical Co Ltd
Priority to PCT/JP2017/021473 priority Critical patent/WO2017213252A1/en
Publication of JP2019089711A publication Critical patent/JP2019089711A/en
Pending legal-status Critical Current

Links

Landscapes

  • Plural Heterocyclic Compounds (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)

Abstract

To provide an oxadiazole compound having excellent controlling activities against a pest.SOLUTION: There is provided a compound represented by the formula (I). [A represents a single bond, ORor O; m represents an integer of 0 to 3; X represents a single bond, CRR, NRor O; Rto Reach independently represent H, a substituted/unsubstituted alkyl, an alkoxy or the like; Rrepresents a substituted/unsubstituted alkyl, a phenyl, H or the like; n represents an integer of 0 to 2; Q represents O, NR, N-CN, N-NOor the like; Rrepresents a substituted/unsubstituted alkyl, H or the like; G represents a benzene ring, a furan ring or the like; Y represents a cycloalkyl, a phenyl, CRRRor the like; Rto Reach independently represent a substituted/unsubstituted alkyl, a heterocycle, H or the like.]SELECTED DRAWING: None

Description

本発明はオキサジアゾール化合物及びその用途に関する。   The present invention relates to oxadiazole compounds and their uses.

特許文献1には、医薬用途として下記式

Figure 2019089711
で示される化合物等が記載されている。 Patent Document 1 describes the following formula as a medical use
Figure 2019089711
The compound etc. which are shown by are described.

国際公開第2013/008162号International Publication No. 2013/008162

本発明は、有害生物に対して優れた防除効力を有する化合物を提供することを課題とする。 An object of the present invention is to provide a compound having excellent control activity against pests.

本発明者は、有害生物に対して優れた防除効力を有する化合物を見出すべく検討した結果、下記式(I)で示される化合物が有害生物に対して優れた防除効力を有することを見出した。
すなわち、本発明は以下のとおりである。
〔1〕 式(I)

Figure 2019089711
〔式中、
Aは、単結合、NR1又は酸素原子を表し、
mは、0〜3のいずれかを表し、
1は、1以上のハロゲン原子を有していてもよいC1−C6アルキル基又は水素原子を表し、
Xは、単結合、CR45、NR6又は酸素原子を表し、
2、R3、R4及びR5は、各々独立して、群Aより選ばれる1以上の置換基を有していてもよいC1−C6アルキル基、群Bより選ばれる1以上の置換基を有していてもよいC1−C6アルコキシ基、群Dより選ばれる1以上の置換基を有していてもよいフェニル基、群Dより選ばれる1以上の置換基を有していてもよいピリジル基、群Dより選ばれる1以上の置換基を有していてもよいC3−C6シクロアルキル基、水素原子、ハロゲン原子、若しくはシアノ基を表すか、又はR2及びR3は、それらが結合する炭素原子と一緒になって3−6員環を形成していてもよく(該3−6員環は群Dより選ばれる1以上の置換基を有していてもよい)、mが2又は3である場合、複数のR2及びR3は同一でも異なっていてもよく、
6は、群Aより選ばれる1以上の置換基を有していてもよいC1−C6アルキル基、1以上のハロゲン原子を有していてもよいC3−C6アルケニル基、1以上のハロゲン原子を有していてもよいC3−C6アルキニル基、1以上のハロゲン原子を有していてもよいC1−C6アルコキシ基、群Dより選ばれる1以上の置換基を有していてもよいC3−C6シクロアルキル基、群Dより選ばれる1以上の置換基を有していてもよいフェニル基、群Dより選ばれる1以上の置換基を有していてもよい5員芳香族ヘテロ環基、群Dより選ばれる1以上の置換基を有していてもよい6員芳香族ヘテロ環基又は水素原子を表し、
nは、0、1又は2を表し、
Qは、酸素原子、NR7、N−CN、N−NO2、N−C(O)R7、N−C(O)OR7又はN−S(O)27を表し(nが2の場合、2つのQは同一でも異なっていてもよい)
7は、ハロゲン原子及びシアノ基からなる群より選ばれる1以上の置換基を有していてもよいC1−C6アルキル基又は水素原子を表し、
Gは、チオフェン環、フラン環、イミダゾール環、オキサゾール環、イソオキサゾール環、チアゾール環、オキサジアゾール環、チアジアゾール環、ピリジン環、ピラジン環、ピリダジン環、ピリミジン環又はベンゼン環{該チオフェン環、該フラン環、該イミダゾール環、該オキサゾール環、該イソオキサゾール環、該チアゾール環、該ピリジン環、該ピラジン環、該ピリダジン環、及び該ピリミジン環は、群Dより選ばれる1以上の置換基を有していてもよい。また、nが0の場合、該ベンゼン環は群Iより選ばれる1以上の置換基を有していてもよく、nが1又は2の場合、該ベンゼン環は群Dより選ばれる1以上の置換基を有していてもよい}を表し、
Yは、群Dより選ばれる1以上の置換基を有していてもよいC3−C6シクロアルキル基、群Dより選ばれる1以上の置換基を有していてもよいフェニル基、群Dより選ばれる1以上の置換基を有していてもよい5員芳香族ヘテロ環基、群Gより選ばれる1以上の置換基を有していてもよい6員芳香族ヘテロ環基、群Dより選ばれる1以上の置換基を有していてもよい3−6員非芳香族ヘテロ環基、CR8910、NR1112又はOR13を表し、
8、R9及びR10は、各々独立して、群A及び群Fからなる群より選ばれる1以上の置換基を有していてもよいC1−C6アルキル基、1以上のハロゲン原子を有していてもよいC3−C6アルケニル基、1以上のハロゲン原子を有していてもよいC3−C6アルキニル基、群Bより選ばれる1以上の置換基を有していてもよいC1−C6アルコキシ基、群Dより選ばれる1以上の置換基を有していてもよいC3−C6シクロアルキル基、群Dより選ばれる1以上の置換基を有していてもよいフェニル基、群Dより選ばれる1以上の置換基を有していてもよい5−6員芳香族ヘテロ環基、水素原子、ハロゲン原子又はシアノ基を表し、
11及びR12は、各々独立して、群E及び群Fからなる群より選ばれる1以上の置換基を有していてもよいC1−C6アルキル基、1以上のハロゲン原子を有していてもよいC3−C6アルケニル基、1以上のハロゲン原子を有していてもよいC3−C6アルキニル基、1以上のハロゲン原子を有していてもよいC1−C6アルコキシ基、群Dより選ばれる1以上の置換基を有していてもよいC3−C6シクロアルキル基、群Dより選ばれる1以上の置換基を有していてもよいフェニル基、群Dより選ばれる1以上の置換基を有していてもよい5−6員芳香族ヘテロ環基若しくは水素原子を表すか、又はR11とR12とは、互いに結合して3−8員ヘテロ環(該3−8員ヘテロ環は群Dより選ばれる1以上の置換基を有していてもよい)を形成していてもよく、
13は、群A及び群Fからなる群より選ばれる1以上の置換基を有していてもよいC1−C6アルキル基、1以上のハロゲン原子を有していてもよいC3−C6アルケニル基、1以上のハロゲン原子を有していてもよいC3−C6アルキニル基、群Dより選ばれる1以上の置換基を有していてもよいC3−C6シクロアルキル基、群Dより選ばれる1以上の置換基を有していてもよいフェニル基、群Dより選ばれる1以上の置換基を有していてもよい5−6員芳香族ヘテロ環基又は水素原子を表し、
XがCR45であり、YがCR8910である場合、R4とR8とは、互いに結合して5−7員ヘテロ環を形成していてもよく(該5−7員ヘテロ環は群Dより選ばれる1以上の置換基を有していてもよい)、
XがCR45であり、YがNR1112である場合、R4とR11とは、互いに結合して5−7員ヘテロ環を形成していてもよく(該5−7員ヘテロ環は群Dより選ばれる1以上の置換基を有していてもよい)、
XがCR45であり、Yが、OR13である場合、R4とR13とは、互いに結合して5−7員ヘテロ環を形成していてもよく(該5−7員ヘテロ環は群Dより選ばれる1以上の置換基を有していてもよい)、
XがNR6であり、YがCR8910である場合、R6とR8とは、互いに結合して5−7員ヘテロ環を形成していてもよく(該5−7員ヘテロ環は群Dより選ばれる1以上の置換基を有していてもよい)、
XがNR6であり、YがNR1112である場合、R6とR11とは、互いに結合して5−7員ヘテロ環を形成していてもよく(該5−7員ヘテロ環は群Dより選ばれる1以上の置換基を有していてもよい)、
XがNR6であり、Yが、OR13である場合、R6とR13とは、互いに結合して5−7員ヘテロ環を形成していてもよい(該5−7員ヘテロ環は群Dより選ばれる1以上の置換基を有していてもよい)。
群A:1以上のハロゲン原子を有していてもよいC1−C6アルコキシ基、1以上のハロゲン原子を有していてもよいC1−C6アルキルチオ基、群Cより選ばれる1以上の置換基を有していてもよいC3−C6シクロアルキル基、群Hより選ばれる1以上の置換基を有していてもよいフェニル基、群Hより選ばれる1以上の置換基を有していてもよい5−6員芳香族ヘテロ環基、ハロゲン原子、ニトロ基及びシアノ基からなる群。
群B:1以上のハロゲン原子を有していてもよいC1−C6アルキルチオ基、群Hより選ばれる1以上の置換基を有していてもよいフェニル基、群Hより選ばれる1以上の置換基を有していてもよい5−6員芳香族ヘテロ環基、ハロゲン原子、ニトロ基及びシアノ基からなる群。
群C:ハロゲン原子、ニトロ基、及びシアノ基からなる群。
群D:群Cより選ばれる1以上の置換基を有していてもよいC1−C6アルキル基、群Cより選ばれる1以上の置換基を有していてもよいC3−C6シクロアルキル基、1以上のハロゲン原子を有していてもよいC1−C6アルコキシ基、1以上のハロゲン原子を有していてもよいC3−C6アルケニルオキシ基、1以上のハロゲン原子を有していてもよいC3−C6アルキニルオキシ基、1以上のハロゲン原子を有していてもよいC1−C6アルキルチオ基、1以上のハロゲン原子を有していてもよいC1−C6アルキルスルホニルオキシ基、ハロゲン原子、シアノ基、及びニトロ基からなる群。
群E:群Cより選ばれる1以上の置換基を有していてもよいC3−C6シクロアルキル基、1以上のハロゲン原子を有していてもよいC1−C6アルコキシ基、1以上のハロゲン原子を有していてもよいC1−C6アルキルチオ基、群Hより選ばれる1以上の置換基を有していてもよいフェニル基、群Hより選ばれる1以上の置換基を有していてもよい5−6員芳香族ヘテロ環基、1以上のハロゲン原子を有していてもよいC1−C6アルキルスルホニル基、1以上のハロゲン原子を有していてもよいC1−C6アルキルスルホニルオキシ基及びハロゲン原子からなる群。
群F:群Cより選ばれる1以上の置換基を有していてもよいC2−C7アルキルカルボニルアミノ基、群Cより選ばれる1以上の置換基を有していてもよいC1−C6アルキルアミノカルボニル基、群Cより選ばれる1以上の置換基を有していてもよいジ(C1−C6アルキル)アミノカルボニル基、群Cより選ばれる1以上の置換基を有していてもよいC1−C6アルキルスルホニルアミノ基、群Cより選ばれる1以上の置換基を有していてもよいC1−C6アルキルアミノスルホニル基及び群Cより選ばれる1以上の置換基を有していてもよいジ(C1−C6アルキル)アミノスルホニル基からなる群。
群G:群Cより選ばれる1以上の置換基を有していてもよいC1−C6アルキル基、群Cより選ばれる1以上の置換基を有していてもよいC3−C6シクロアルキル基、1以上のハロゲン原子を有していてもよいC1−C6アルコキシ基、1以上のハロゲン原子を有していてもよいC3−C6アルケニルオキシ基、1以上のハロゲン原子を有していてもよいC3−C6アルキニルオキシ基、1以上のハロゲン原子を有していてもよいC1−C6アルキルチオ基、1以上のハロゲン原子を有していてもよいC1−C6アルキルスルホニルオキシ基、ハロゲン原子、及びニトロ基からなる群。
群H:1以上のハロゲン原子を有していてもよいC1−C6アルキル基、1以上のハロゲン原子を有していてもよいC1−C6アルコキシ基、ハロゲン原子及びシアノ基からなる群。
群I:群Cより選ばれる1以上の置換基を有していてもよいC1−C6アルキル基、群Cより選ばれる1以上の置換基を有していてもよいC3−C6シクロアルキル基、1以上のハロゲン原子を有していてもよいC3−C6アルケニルオキシ基、1以上のハロゲン原子を有していてもよいC3−C6アルキニルオキシ基、1以上のハロゲン原子を有していてもよいC1−C6アルキルチオ基、1以上のハロゲン原子を有していてもよいC1−C6アルキルスルホニルオキシ基、フッ素原子及びシアノ基からなる群。〕
で示される化合物(以下、本発明化合物と記す)。
〔2〕 Aが単結合であり、mが0であり、
Gがベンゼン環又はピリジン環(該ベンゼン環及び該ピリジン環は1以上のフッ素原子を有していてもよい)であり、
Xが単結合又はNR6であり、
Qが酸素原子、NH、N−CN、N−C(O)R7又はN−C(O)OR7であり、
7がC1−C6アルキル基であり、
Yが1以上のハロゲン原子を有していてもよいC3−C6シクロアルキル基、1以上のハロゲン原子を有していてもよいフェニル基、CR8910又はNR1112であり、
6がC1−C6アルキル基(該C1−C6アルキル基は、ハロゲン原子、C1−C6アルコキシ基、C1−C6アルキルチオ基、C3−C6シクロアルキル基及びフェニル基からなる群より選ばれる1以上の置換基を有していてもよい)、1以上のハロゲン原子を有していてもよいC3−C6アルキニル基、1以上のハロゲン原子を有していてもよいC3−C6シクロアルキル基、フェニル基(該フェニル基はハロゲン原子、C1−C6アルキル基又はC1−C6アルコキシ基からなる群より選ばれる1以上の置換基を有していてもよい)又は水素原子であり、
8、R9及びR10が、各々独立して、1以上のハロゲン原子を有していてもよいC1−C6アルキル基、フェニル基、水素原子又はハロゲン原子であり、
11及びR12が、各々独立して、水素原子又はC1−C6アルキル基であり、
Aが、Gにあたるベンゼン環又はピリジン環上で、オキサジアゾール環に対してパラ位に結合している〔1〕に記載の化合物。
〔3〕 Aが単結合であり、mが0であり、
Gがベンゼン環又はピリジン環であり(該ベンゼン環及び該ピリジン環は1以上のフッ素原子を有していてもよい)、
Xが単結合又はNR6であり、
Qが酸素原子、NH又はN−CNであり、
Yが1以上のハロゲン原子を有していてもよいC3−C6シクロアルキル基、CR8910又はNR1112であり、
6が1以上のハロゲン原子を有していてもよいC1−C6アルキル基又は水素原子であり、
8、R9及びR10が、各々独立して1以上のハロゲン原子を有していてもよいC1−C6アルキル基又は水素原子であり、
11及びR12が、各々独立してC1−C6アルキル基(該C1−C6アルキル基はハロゲン原子、C3−C6シクロアルキル基及びC1−C6アルコキシ基からなる群より選ばれる1以上の置換基を有していてもよい)、1以上のハロゲン原子を有していてもよいC3−C6アルキニル基、1以上のハロゲン原子を有していてもよいC3−C6シクロアルキル基若しくは水素原子であるか、又はR11とR12とが互いに結合して3−6員ヘテロ環(該3−6員ヘテロ環は1以上のハロゲン原子を有していてもよい)を形成している、〔1〕又は〔2〕に記載の化合物。
〔4〕 Gが1以上のフッ素原子を有していてもよいベンゼン環であり、
Yが1以上のハロゲン原子を有していてもよいC3−C6シクロアルキル基又はCR8910である、〔1〕〜〔3〕のいずれかに記載の化合物。
〔5〕 Gが1以上のフッ素原子を有していてもよいベンゼン環であり、Xが単結合であり、YがCR8910である、〔1〕〜〔4〕のいずれかに記載の化合物。
〔6〕 Gが1以上のフッ素原子を有していてもよいベンゼン環であり、XがNR6であり、nが2であり、Qが酸素原子であり、YがCR8910又は1以上のハロゲン原子を有していてもよいC3−C6シクロアルキル基である、〔1〕〜〔4〕のいずれかに記載の化合物。
〔7〕 Gが1以上のフッ素原子を有していてもよいベンゼン環であり、Xが単結合であり、nが2であり、Qが酸素原子であり、YがNR1112である、〔1〕〜〔3〕のいずれかに記載の化合物。
〔8〕 〔1〕〜〔7〕のいずれかに記載の化合物を含有する有害生物防除剤(以下、本発明防除剤とも記す)。
〔9〕 〔1〕〜〔7〕のいずれかに記載の化合物の有効量を植物又は土壌に処理することによる、有害生物の防除方法。
〔10〕 有害生物を防除するための〔1〕〜〔7〕のいずれかに記載の化合物の使用。
〔11〕 殺菌剤、殺虫剤、殺ダニ剤、殺センチュウ剤、植物成長調節剤及び共力剤からなる群より選ばれる1以上、並びに、〔1〕〜〔7〕いずれかに記載の化合物を含有する組成物。 As a result of examining to find a compound having an excellent controlling effect on pests, the present inventor has found that a compound represented by the following formula (I) has an excellent controlling effect on pests.
That is, the present invention is as follows.
[1] Formula (I)
Figure 2019089711
[In the formula,
A represents a single bond, NR 1 or an oxygen atom,
m represents any of 0 to 3;
R 1 represents a C1-C6 alkyl group optionally having one or more halogen atoms or a hydrogen atom,
X represents a single bond, CR 4 R 5 , NR 6 or an oxygen atom,
R 2 , R 3 , R 4 and R 5 are each independently a C 1 -C 6 alkyl group optionally having one or more substituents selected from group A, one or more substituents selected from group B A C1-C6 alkoxy group which may have a group, a phenyl group which may have one or more substituents selected from group D, and one or more substituents selected from group D A pyridyl group, a C3-C6 cycloalkyl group optionally having one or more substituents selected from group D, a hydrogen atom, a halogen atom, or a cyano group, or R 2 and R 3 M may be taken together with the carbon atom to which it is attached to form a 3- to 6-membered ring (the 3- to 6-membered ring may have one or more substituents selected from Group D), m When is 2 or 3, the plurality of R 2 and R 3 may be the same or different,
R 6 is a C 1 -C 6 alkyl group which may have one or more substituents selected from group A, a C 3 -C 6 alkenyl group which may have one or more halogen atoms, one or more halogen atoms C 3 -C 6 alkynyl group which may have one or more substituents, C 1 -C 6 alkoxy group which may have one or more halogen atoms, C 3-which may have one or more substituents selected from group D A C6 cycloalkyl group, a phenyl group optionally having one or more substituents selected from group D, a 5-membered aromatic heterocyclic group optionally having one or more substituents selected from group D, A 6-membered aromatic heterocyclic group or a hydrogen atom which may have one or more substituents selected from group D,
n represents 0, 1 or 2;
Q represents an oxygen atom, NR 7 , N-CN, N-NO 2 , N-C (O) R 7 , N-C (O) OR 7 or N-S (O) 2 R 7 (n is In the case of 2, two Q may be the same or different)
R 7 represents a C 1 -C 6 alkyl group optionally having one or more substituents selected from the group consisting of a halogen atom and a cyano group, or a hydrogen atom,
G is a thiophene ring, furan ring, imidazole ring, oxazole ring, isoxazole ring, thiazole ring, oxadiazole ring, thiadiazole ring, pyridine ring, pyrazine ring, pyridazine ring, pyrimidine ring or benzene ring {the thiophene ring, The furan ring, the imidazole ring, the oxazole ring, the isoxazole ring, the thiazole ring, the pyridine ring, the pyrazine ring, the pyridazine ring, and the pyrimidine ring have one or more substituents selected from group D. It may be done. In addition, when n is 0, the benzene ring may have one or more substituents selected from group I. When n is 1 or 2, the benzene ring is one or more selected from group D. Represents an optionally substituted substituent},
Y is a C3-C6 cycloalkyl group optionally having one or more substituents selected from group D, a phenyl group optionally having one or more substituents selected from group D, a group D 5-membered aromatic heterocyclic group optionally having one or more substituents selected, 6-membered aromatic heterocyclic group optionally having one or more substituents selected from group G, from group D Represents a 3- to 6-membered non-aromatic heterocyclic group optionally having one or more substituents, CR 8 R 9 R 10 , NR 11 R 12 or OR 13 ,
R 8 , R 9 and R 10 each independently represent a C1-C6 alkyl group optionally having one or more substituents selected from the group consisting of Group A and Group F, and one or more halogen atoms C3-C6 alkenyl group which may have, C3-C6 alkynyl group which may have one or more halogen atoms, C1-C6 which may have one or more substituents selected from group B Alkoxy group, C3-C6 cycloalkyl group optionally having one or more substituents selected from group D, phenyl group optionally having one or more substituents selected from group D, group D Represents a 5- to 6-membered aromatic heterocyclic group optionally having one or more substituents, a hydrogen atom, a halogen atom or a cyano group,
R 11 and R 12 each independently have a C 1 -C 6 alkyl group optionally having one or more substituents selected from the group consisting of Group E and Group F, and one or more halogen atoms A C3-C6 alkenyl group which may be, a C3-C6 alkynyl group which may have one or more halogen atoms, a C1-C6 alkoxy group which may have one or more halogen atoms, a group D C3-C6 cycloalkyl group which may have one or more substituents, phenyl group which may have one or more substituents selected from group D, one or more substituents selected from group D Represents a 5- to 6-membered aromatic heterocyclic group or hydrogen atom which may be possessed, or R 11 and R 12 are bonded to each other to form a 3- to 8-membered heterocyclic ring (the 3- to 8-membered heterocyclic ring is Form one or more substituents selected from group D) Even if well,
R 13 is a C1-C6 alkyl group optionally having one or more substituents selected from the group consisting of Group A and Group F, and a C3-C6 alkenyl group optionally having one or more halogen atoms A C3-C6 alkynyl group optionally having one or more halogen atoms, a C3-C6 cycloalkyl group optionally having one or more substituents selected from group D, one or more selected from group D Or a substituted or unsubstituted phenyl group, a 5-6 membered aromatic heterocyclic group optionally having one or more substituents selected from group D, or a hydrogen atom,
When X is CR 4 R 5 and Y is CR 8 R 9 R 10 , R 4 and R 8 may be combined with each other to form a 5-7 membered heterocyclic ring (the 7-membered heterocyclic ring may have one or more substituents selected from group D),
When X is CR 4 R 5 and Y is NR 11 R 12 , R 4 and R 11 may be combined with each other to form a 5-7 membered heterocyclic ring (the 5-7 membered member) The heterocycle may have one or more substituents selected from group D),
When X is CR 4 R 5 and Y is OR 13 , R 4 and R 13 may be bonded to each other to form a 5-7 membered hetero ring (the 5-7 membered hetero ring) The ring may have one or more substituents selected from group D),
When X is NR 6 and Y is CR 8 R 9 R 10 , R 6 and R 8 may be combined with each other to form a 5-7 membered heterocyclic ring (the 5-7 membered member) The heterocycle may have one or more substituents selected from group D),
When X is NR 6 and Y is NR 11 R 12 , R 6 and R 11 may be bonded to each other to form a 5- to 7-membered heterocyclic ring (the 5- to 7-membered heterocyclic ring) And may have one or more substituents selected from group D),
When X is NR 6 and Y is OR 13 , R 6 and R 13 may be bonded to each other to form a 5-7 membered heterocycle (the 5-7 membered heterocycle is It may have one or more substituents selected from group D).
Group A: C1-C6 alkoxy group optionally having one or more halogen atoms, C1-C6 alkylthio group optionally having one or more halogen atoms, one or more substituents selected from group C A C3-C6 cycloalkyl group which may have, a phenyl group which may have one or more substituents selected from group H, and one or more substituents selected from group H A group consisting of a 5- to 6-membered aromatic heterocyclic group, a halogen atom, a nitro group and a cyano group.
Group B: C1-C6 alkylthio group optionally having one or more halogen atoms, phenyl group optionally having one or more substituents selected from group H, one or more substituents selected from group H A group comprising a 5- to 6-membered aromatic heterocyclic group which may have a group, a halogen atom, a nitro group and a cyano group.
Group C: a group consisting of a halogen atom, a nitro group, and a cyano group.
Group D: C1-C6 alkyl group optionally having one or more substituents selected from group C, C3-C6 cycloalkyl group optionally having one or more substituents selected from group C, C1-C6 alkoxy group optionally having one or more halogen atoms, C3-C6 alkenyloxy group optionally having one or more halogen atoms, C3 optionally having one or more halogen atoms -C6 alkynyloxy group, C1-C6 alkylthio group optionally having one or more halogen atoms, C1-C6 alkylsulfonyloxy group optionally having one or more halogen atoms, halogen atom, cyano group, And a nitro group.
Group E: C3-C6 cycloalkyl group optionally having one or more substituents selected from group C, C1-C6 alkoxy group optionally having one or more halogen atoms, one or more halogen atoms A C1-C6 alkylthio group which may have one or more substituents, a phenyl group which may have one or more substituents selected from group H, and one or more substituents selected from group H 5-6 membered aromatic heterocyclic group, C1-C6 alkylsulfonyl group optionally having one or more halogen atoms, C1-C6 alkylsulfonyloxy group optionally having one or more halogen atoms, and halogen A group of atoms.
Group F: C2 to C7 alkylcarbonylamino group optionally having one or more substituents selected from group C, C1 to C6 alkylamino optionally having one or more substituents selected from group C A carbonyl group, a di (C 1 -C 6 alkyl) aminocarbonyl group optionally having one or more substituents selected from group C, a C 1-optionally having one or more substituents selected from group C A C6 alkylsulfonylamino group, a C1-C6 alkylaminosulfonyl group optionally having one or more substituents selected from group C, and one or more substituents optionally selected from group C The group which consists of a C1-C6 alkyl) aminosulfonyl group.
Group G: C1-C6 alkyl group optionally having one or more substituents selected from group C, C3-C6 cycloalkyl group optionally having one or more substituents selected from group C, C1-C6 alkoxy group optionally having one or more halogen atoms, C3-C6 alkenyloxy group optionally having one or more halogen atoms, C3 optionally having one or more halogen atoms -C6 alkynyloxy group, C1-C6 alkylthio group optionally having one or more halogen atoms, C1-C6 alkylsulfonyloxy group optionally having one or more halogen atoms, halogen atom, and nitro group A group consisting of
Group H: a group consisting of a C1 to C6 alkyl group optionally having one or more halogen atoms, a C1 to C6 alkoxy group optionally having one or more halogen atoms, a halogen atom and a cyano group.
Group I: C1-C6 alkyl group optionally having one or more substituents selected from group C, C3-C6 cycloalkyl group optionally having one or more substituents selected from group C, C3-C6 alkenyloxy group optionally having one or more halogen atoms, C3-C6 alkynyloxy group optionally having one or more halogen atoms, optionally having one or more halogen atoms A group consisting of a C1-C6 alkylthio group, a C1-C6 alkylsulfonyloxy group optionally having one or more halogen atoms, a fluorine atom and a cyano group. ]
And a compound represented by (hereinafter, referred to as the present compound).
[2] A is a single bond, m is 0,
G is a benzene ring or a pyridine ring (the benzene ring and the pyridine ring may have one or more fluorine atoms),
X is a single bond or NR 6 ,
Q is an oxygen atom, NH, N-CN, a N-C (O) R 7 or N-C (O) OR 7 ,
R 7 is a C1-C6 alkyl group,
Y is a C3-C6 cycloalkyl group which may have one or more halogen atoms, a phenyl group which may have one or more halogen atoms, CR 8 R 9 R 10 or NR 11 R 12 ,
R 6 is a C 1 -C 6 alkyl group (wherein the C 1 -C 6 alkyl group is one or more selected from the group consisting of a halogen atom, a C 1 -C 6 alkoxy group, a C 1 -C 6 alkylthio group, a C 3 -C 6 cycloalkyl group and a phenyl group Optionally substituted), C3-C6 alkynyl group optionally having one or more halogen atoms, C3-C6 cycloalkyl group optionally having one or more halogen atoms, phenyl group (The phenyl group may have one or more substituents selected from the group consisting of a halogen atom, a C1-C6 alkyl group or a C1-C6 alkoxy group) or a hydrogen atom,
R 8 , R 9 and R 10 each independently represent a C1-C6 alkyl group optionally having one or more halogen atoms, a phenyl group, a hydrogen atom or a halogen atom,
R 11 and R 12 are each independently a hydrogen atom or a C 1 -C 6 alkyl group,
The compound according to [1], wherein A is bonded to the benzene ring or pyridine ring corresponding to G at a position para to the oxadiazole ring.
[3] A is a single bond, m is 0,
G is a benzene ring or a pyridine ring (the benzene ring and the pyridine ring may have one or more fluorine atoms),
X is a single bond or NR 6 ,
Q is an oxygen atom, NH or N-CN,
Y is a C3-C6 cycloalkyl group optionally having one or more halogen atoms, CR 8 R 9 R 10 or NR 11 R 12 ,
R 6 is a C 1 -C 6 alkyl group optionally having one or more halogen atoms, or a hydrogen atom,
R 8 , R 9 and R 10 each independently represent a C1-C6 alkyl group optionally having one or more halogen atoms, or a hydrogen atom,
Each of R 11 and R 12 independently represents a C 1 -C 6 alkyl group (wherein the C 1 -C 6 alkyl group is a halogen atom, a C 3 -C 6 cycloalkyl group, and a C 1 -C 6 alkoxy group) A C3-C6 alkynyl group optionally having one or more halogen atoms, a C3-C6 cycloalkyl group optionally having one or more halogen atoms, or a hydrogen atom Or R 11 and R 12 are bonded to each other to form a 3- to 6-membered heterocyclic ring (the 3- to 6-membered heterocyclic ring may have one or more halogen atoms), [1 Or a compound described in [2].
[4] G is a benzene ring which may have one or more fluorine atoms,
The compound in any one of [1]-[3] whose Y is a C3-C6 cycloalkyl group or CR < 8 > R < 9 > R < 10 > which may have one or more halogen atoms.
[5] Any one of [1] to [4], wherein G is a benzene ring optionally having one or more fluorine atoms, X is a single bond, and Y is CR 8 R 9 R 10 The compound as described in.
[6] G is a benzene ring which may have one or more fluorine atoms, X is NR 6 , n is 2 and Q is an oxygen atom, and Y is CR 8 R 9 R 10 Or the compound in any one of [1]-[4] which is the C3-C6 cycloalkyl group which may have one or more halogen atoms.
[7] G is a benzene ring which may have one or more fluorine atoms, X is a single bond, n is 2, Q is an oxygen atom, and Y is NR 11 R 12 And the compound in any one of [1]-[3].
[8] A pest control agent containing the compound according to any one of [1] to [7] (hereinafter also referred to as the control agent of the present invention).
[9] A method for controlling a pest by treating a plant or soil with an effective amount of the compound according to any one of [1] to [7].
[10] Use of the compound according to any one of [1] to [7] for controlling pests.
[11] One or more members selected from the group consisting of fungicides, insecticides, acaricides, nematocides, plant growth regulators and synergists, and a compound according to any one of [1] to [7] Composition to contain.

本発明により、有害生物を防除することができる。   According to the present invention, pests can be controlled.

本明細書における置換基について説明する。
本明細書において、
置換基が2以上のハロゲン原子を有する場合、それらのハロゲン原子は各々同一でも異なっていてもよい。
本明細書における「CX−CY」との表記は、炭素原子数がX乃至Yであることを意味する。例えば「C1−C6」の表記は、炭素原子数が1乃至6であることを意味する。
The substituents in the present specification will be described.
In the present specification,
When the substituent has two or more halogen atoms, those halogen atoms may be the same or different.
The notation "CX-CY" in the present specification means that the number of carbon atoms is X to Y. For example, the notation "C1-C6" means that the number of carbon atoms is 1 to 6.

ハロゲン原子とは、フッ素原子、塩素原子、臭素原子又はヨウ素原子を表す。
「アルキル基」としては、例えばメチル基、エチル基、プロピル基、イソプロピル基、1,1−ジメチルプロピル基、1,2−ジメチルプロピル基、1−エチルプロピル基、ブチル基、イソブチル基、tert−ブチル基、ペンチル基及びヘキシル基が挙げられる。
「アルケニル基」としては、例えばビニル基、1−プロペニル基、2−プロペニル基、1−メチル−1−プロペニル基、1−メチル−2−プロペニル基、1,2−ジメチル−1−プロペニル基、1,1−ジメチル−2−プロペニル基、1−エチル−1−プロペニル基、1−エチル−2−プロペニル基、3−ブテニル基、4−ペンテニル基及び5−ヘキセニル基が挙げられる。
「アルキニル基」としては、例えばエチニル基、1−プロピニル基、2−プロピニル基、1−メチル−2−プロピニル基、1,1−ジメチル−2−プロピニル基、1−エチル−2−プロピニル基、2−ブチニル基、4−ペンチニル基及び5−ヘキシニル基が挙げられる。
「5−6員芳香族ヘテロ環基」とは、5員芳香族ヘテロ環基又は6員芳香族ヘテロ環基を表し、5員芳香族ヘテロ環基とはピロリル基、フリル基、チエニル基、ピラゾリル基、イミダゾリル基、トリアゾリル基、テトラゾリル基、オキサゾリル基、イソオキサゾリル基、チアゾリル基、オキサジアゾリル基、又はチアジアゾリル基を表し、6員芳香族ヘテロ環基とはピリジル基、ピリダジニル基、ピリミジニル基又はピラジニル基を表す。
The halogen atom represents a fluorine atom, a chlorine atom, a bromine atom or an iodine atom.
As the "alkyl group", for example, methyl group, ethyl group, propyl group, isopropyl group, 1,1-dimethylpropyl group, 1,2-dimethylpropyl group, 1-ethylpropyl group, butyl group, isobutyl group, tert- Examples include butyl, pentyl and hexyl.
As the “alkenyl group”, for example, a vinyl group, 1-propenyl group, 2-propenyl group, 1-methyl-1-propenyl group, 1-methyl-2-propenyl group, 1,2-dimethyl-1-propenyl group, 1,1-dimethyl-2-propenyl group, 1-ethyl-1-propenyl group, 1-ethyl-2-propenyl group, 3-butenyl group, 4-pentenyl group and 5-hexenyl group can be mentioned.
As the “alkynyl group”, for example, ethynyl group, 1-propynyl group, 2-propynyl group, 1-methyl-2-propynyl group, 1,1-dimethyl-2-propynyl group, 1-ethyl-2-propynyl group, Examples include 2-butynyl group, 4-pentynyl group and 5-hexynyl group.
The “5-6 membered aromatic heterocyclic group” represents a 5-membered aromatic heterocyclic group or a 6-membered aromatic heterocyclic group, and the 5-membered aromatic heterocyclic group represents a pyrrolyl group, a furyl group, a thienyl group, Represents a pyrazolyl group, an imidazolyl group, a triazolyl group, a tetrazolyl group, an oxazolyl group, an isoxazolyl group, a thiazolyl group, an oxadiazolyl group or a thiadiazolyl group, and the 6-membered aromatic heterocyclic group is a pyridyl group, a pyridazinyl group, a pyrimidinyl group or a pyrazinyl group Represents

本発明化合物において、R2及びR3が、それらが結合する炭素原子と一緒になって3−6員環を形成する化合物とは、下記(ZA1〜ZA4)に示すいずれかの構造を表す。

Figure 2019089711
In the compound of the present invention, a compound in which R 2 and R 3 together with the carbon atom to which they are bonded form a 3- to 6-membered ring represents any of the structures shown in the following (ZA1 to ZA4).
Figure 2019089711

NR1112において、R11とR12とが、互いに結合して形成される3−8員ヘテロ環とは、下記(ZB1〜ZB21)に示すいずれかの構造を表す(●は結合位置を表す)。 In NR 11 R 12 , the 3-8 membered heterocyclic ring formed by combining R 11 and R 12 with each other represents any of the structures shown in (ZB 1 to ZB 21) below (● represents the bonding position: Represent).

NR1112において、R11とR12とが、互いに結合して形成される3−6員ヘテロ環とは、下記(ZB1〜ZB4及びZB7〜ZB21)に示すいずれかの構造を表す(●は結合位置を表す)。 In NR 11 R 12 , the 3- to 6-membered heterocyclic ring formed by combining R 11 and R 12 with each other represents any of the structures shown in the following (ZB 1 to ZB 4 and ZB 7 to ZB 21) (● Represents a bonding position).


Figure 2019089711

Figure 2019089711

XがCR45であり、YがCR8910である場合、R4とR8とが互いに結合して形成される5−7員ヘテロ環とは、下記(ZC1〜ZC3)に示すいずれかの構造を表す(●は結合位置を表す)。

Figure 2019089711
When X is CR 4 R 5 and Y is CR 8 R 9 R 10 , the 5- to 7-membered heterocycle formed by bonding R 4 and R 8 to each other is the following (ZC1 to ZC3): Represents any of the structures shown in (where ● represents a bonding position).
Figure 2019089711

XがCR45であり、YがNR1112である場合、R4とR11とが互いに結合して形成される5−7員ヘテロ環とは、下記(ZD1〜ZD3)に示すいずれかの構造を表す(●は結合位置を表す)。

Figure 2019089711
When X is CR 4 R 5 and Y is NR 11 R 12 , the 5-7 membered heterocyclic ring formed by bonding R 4 and R 11 to each other is represented by the following (ZD 1 to ZD 3) Represents any structure (● represents a bonding position).
Figure 2019089711

XがCR45であり、Yが、OR13である場合、R4とR13とが互いに結合して形成される5−7員ヘテロ環とは、下記(ZE1〜ZE3)に示すいずれかの構造を表す(●は結合位置を表す)。

Figure 2019089711
When X is CR 4 R 5 and Y is OR 13 , the 5-7 membered heterocyclic ring formed by bonding R 4 and R 13 to each other is any of the following (ZE 1 to ZE 3): Represents the structure of the compound (● represents the bonding position).
Figure 2019089711

XがNR6であり、YがCR8910である場合、R6とR8とが互いに結合して形成される5−7員ヘテロ環とは、下記(ZF1〜ZF3)に示すいずれかの構造を表す(●は結合位置を表す)。 When X is NR 6 and Y is CR 8 R 9 R 10 , the 5-7 membered heterocyclic ring formed by bonding R 6 and R 8 to each other is represented by the following (ZF 1 to ZF 3) Represents any structure (● represents a bonding position).

Figure 2019089711
Figure 2019089711

XがNR6であり、YがNR1112である場合、R6とR11とが互いに結合して形成される5−7員ヘテロ環とは、下記(ZG1〜ZG4)に示すいずれかの構造を表す(●は結合位置を表す)。

Figure 2019089711
When X is NR 6 and Y is NR 11 R 12 , the 5-7 membered heterocyclic ring formed by bonding R 6 and R 11 to each other is any one of the following (ZG 1 to ZG 4): Represents the structure of (where ● represents a bonding position).
Figure 2019089711

XがNR6であり、Yが、OR13である場合、R6とR13とが互いに結合して形成される5−7員飽ヘテロ環とは、下記(ZH1〜ZH3)に示すいずれかの構造を表す(●は結合位置を表す)。

Figure 2019089711
When X is NR 6 and Y is OR 13 , the 5-7 member saturated heterocycle formed by bonding R 6 and R 13 to each other is any one of the following (ZH 1 to ZH 3): Represents the structure of (where ● represents a bonding position).
Figure 2019089711

1個又は複数個の不斉中心を含む本発明化合物には、各々の光学異性体及びそれらが任意の割合で含まれる混合物が含まれる。また、炭素−炭素二重結合、炭素−窒素結合、硫黄−酸素結合、硫黄−窒素結合、環状構造等に由来する2種以上の幾何異性体を含む本発明化合物には、各々の幾何異性体及びそれらが任意の割合で含まれる混合物が含まれる。 Compounds of the present invention containing one or more asymmetric centers include the respective optical isomers and mixtures containing them in any proportion. In addition, the compound of the present invention containing two or more geometric isomers derived from carbon-carbon double bond, carbon-nitrogen bond, sulfur-oxygen bond, sulfur-nitrogen bond, cyclic structure etc. And mixtures containing them in any proportion.

本発明化合物は、塩酸、硫酸、硝酸、リン酸、酢酸又は安息香酸等の酸と混合することにより、塩酸塩、硫酸塩、硝酸塩、リン酸塩、酢酸塩又は安息香酸塩等の酸付加塩を形成することがある。 The compound of the present invention is mixed with an acid such as hydrochloric acid, sulfuric acid, nitric acid, phosphoric acid, acetic acid or benzoic acid to produce an acid addition salt such as hydrochloride, sulfate, nitrate, phosphate, acetate or benzoate. May form.

本発明化合物の態様としては、以下の化合物が挙げられる。 The following compounds may be mentioned as embodiments of the compound of the present invention.

[態様1] 本発明化合物において、Gがベンゼン環又はピリジン環であり(該ベンゼン環及び該ピリジン環は1以上のフッ素原子を有していてもよい)、Xが単結合又はNR6であり、Qが酸素原子、NH又はN−CNであり、Yが1以上のハロゲン原子を有していてもよいC3−C6シクロアルキル基、CR8910又はNR1112であり、R6が1以上のハロゲン原子を有していてもよいC1−C6アルキル基又は水素原子であり、R8、R9及びR10が、各々独立して1以上のハロゲン原子を有していてもよいC1−C6アルキル基又は水素原子であり、R11及びR12が、各々独立して、C1−C6アルキル基(該C1−C6アルキル基はハロゲン原子、C3−C6シクロアルキル基及びC1−C6アルコキシ基からなる群より選ばれる1以上の置換基を有していてもよい)、1以上のハロゲン原子を有していてもよいC3−C6アルキニル基、1以上のハロゲン原子を有していてもよいC3−C6シクロアルキル基、若しくは水素原子であるか、又はR11とR12とが互いに結合して3−6員ヘテロ環(該3−6員ヘテロ環は1以上のハロゲン原子を有していてもよい)を形成している化合物。
[態様2] 本発明化合物において、Gがベンゼン環であり(該ベンゼン環は1以上のフッ素原子を有していてもよい)、Xが単結合又はNR6であり、Qが酸素原子、NH又はN−CNであり、Yが1以上のハロゲン原子を有していてもよいC3−C6シクロアルキル基、CR8910又はNR1112であり、R6が1以上のハロゲン原子を有していてもよいC1−C6アルキル基又は水素原子であり、R8、R9及びR10が、各々独立して、1以上のハロゲン原子を有していてもよいC1−C6アルキル基又は水素原子であり、R11及びR12が、各々独立して、C1−C6アルキル基(該C1−C6アルキル基はハロゲン原子、C3−C6シクロアルキル基及びC1−C6アルコキシ基からなる群より選ばれる1以上の置換基を有していてもよい)、1以上のハロゲン原子を有していてもよいC3−C6アルキニル基、1以上のハロゲン原子を有していてもよいC3−C6シクロアルキル基、若しくは水素原子であるか、又はR11とR12とが互いに結合して3−6員ヘテロ環(該3−6員ヘテロ環は1以上のハロゲン原子を有していてもよい)を形成している化合物。
[態様3] 本発明化合物において、Gがベンゼン環であり(該ベンゼン環は1以上のフッ素原子を有していてもよい)、Xが単結合又はNR6であり、Qが酸素原子、NH又はN−CNであり、Yが1以上のハロゲン原子を有していてもよいC3−C6シクロアルキル基、CR8910又はNR1112であり、R6が1以上のハロゲン原子を有していてもよいC1−C6アルキル基又は水素原子であり、R8、R9及びR10が、各々独立して1以上のハロゲン原子を有していてもよいC1−C6アルキル基又は水素原子であり、R11及びR12が、各々独立して、C1−C6アルキル基(該C1−C6アルキル基はハロゲン原子、C3−C6シクロアルキル基及びC1−C6アルコキシ基からなる群より選ばれる1以上の置換基を有していてもよい)、1以上のハロゲン原子を有していてもよいC3−C6アルキニル基、1以上のハロゲン原子を有していてもよいC3−C6シクロアルキル基、若しくは水素原子であるか、又はR11とR12とが互いに結合して3−6員ヘテロ環(該3−6員ヘテロ環は1以上のハロゲン原子を有していてもよい)を形成しており、Aがオキサジアゾール環に対してパラ位又はメタ位に結合する化合物。
[態様4] 本発明化合物において、Gがベンゼン環であり(該ベンゼン環は1以上のフッ素原子を有していてもよい)、Xが単結合又はNR6であり、Qが酸素原子、NH又はN−CNであり、Yが1以上のハロゲン原子を有していてもよいC3−C6シクロアルキル基、CR8910又はNR1112であり、R6が1以上のハロゲン原子を有していてもよいC1−C6アルキル基又は水素原子であり、R8、R9及びR10が、各々独立して、1以上のハロゲン原子を有していてもよいC1−C6アルキル基又は水素原子であり、R11及びR12が、各々独立して、C1−C6アルキル基(該C1−C6アルキル基はハロゲン原子、C3−C6シクロアルキル基及びC1−C6アルコキシ基からなる群より選ばれる1以上の置換基を有していてもよい)、1以上のハロゲン原子を有していてもよいC3−C6アルキニル基、1以上のハロゲン原子を有していてもよいC3−C6シクロアルキル基、若しくは水素原子であるか、又はR11とR12とが互いに結合して3−6員ヘテロ環(該3−6員ヘテロ環は1以上のハロゲン原子を有していてもよい)を形成しており、Aがオキサジアゾール環に対してパラ位又に結合する化合物。
[態様5] 本発明化合物において、Gがベンゼン環であり、mが0であり、Xが単結合又はNR6であり、Qが酸素原子であり、nが2であり、YがC3−C6シクロアルキル基、CR8910又はNR1112であり、R6が1以上のハロゲン原子を有していてもよいC1−C6アルキル基、C3−C6アルキニル基、C3−C6シクロアルキル基、又は水素原子であり、R8、R9及びR10が、各々独立して、C1−C6アルキル基又は水素原子であり、R11及びR12が、各々独立して、C1−C6アルキル基であり、Aがベンゼン環上でオキサジアゾール環に対してパラ位に結合する化合物。
[態様6] 本発明化合物において、Gがベンゼン環であり、mが0であり、Xが単結合又はNR6であり、Qが酸素原子であり、nが2であり、YがC3−C6シクロアルキル基又はCR8910であり、R6が1以上のハロゲン原子を有していてもよいC1−C6アルキル基、C3−C6アルキニル基、C3−C6シクロアルキル基、又は水素原子であり、R8、R9及びR10が、各々独立して、C1−C6アルキル基又は水素原子であり、Aがベンゼン環上でオキサジアゾール環に対してパラ位に結合する化合物。
[Aspect 1] In the compound of the present invention, G is a benzene ring or a pyridine ring (the benzene ring and the pyridine ring may have one or more fluorine atoms), and X is a single bond or NR 6 . , Q is an oxygen atom, NH or N-CN, and Y is a C3-C6 cycloalkyl group optionally having one or more halogen atoms, CR 8 R 9 R 10 or NR 11 R 12 , R 6 is a C1-C6 alkyl group or a hydrogen atom which may have one or more halogen atoms, and R 8 , R 9 and R 10 each independently have one or more halogen atoms R 11 and R 12 each independently represent a C 1 -C 6 alkyl group (wherein the C 1 -C 6 alkyl group is a halogen atom, a C 3 -C 6 cycloalkyl group and a C 1 -C 6 alkyl group; Selected from the group consisting of alkoxy groups C3-C6 alkynyl group optionally having one or more substituents, C3-C6 alkynyl group optionally having one or more halogen atoms, C3-C6 cycloalkyl group optionally having one or more halogen atoms Or a hydrogen atom, or R 11 and R 12 are bonded to each other to form a 3-6 membered heterocycle (wherein the 3-6 membered heterocycle may have one or more halogen atoms) Compounds that
[Aspect 2] In the compound of the present invention, G is a benzene ring (the benzene ring may have one or more fluorine atoms), X is a single bond or NR 6 , and Q is an oxygen atom, NH Or N-CN, Y is a C3-C6 cycloalkyl group optionally having one or more halogen atoms, CR 8 R 9 R 10 or NR 11 R 12 , and R 6 is one or more halogen atoms A C1 to C6 alkyl group which may have one or more hydrogen atoms, and R 8 , R 9 and R 10 each independently have one or more halogen atoms. Or a hydrogen atom, each of R 11 and R 12 independently being a C 1 -C 6 alkyl group (wherein the C 1 -C 6 alkyl group is a halogen atom, a C 3 -C 6 cycloalkyl group and a C 1 -C 6 alkoxy group Even if it has one or more substituents selected Or a C3-C6 alkynyl group optionally having one or more halogen atoms, a C3-C6 cycloalkyl group optionally having one or more halogen atoms, or a hydrogen atom, or R 11 And R 12 are bonded to each other to form a 3- to 6-membered heterocyclic ring (the 3- to 6-membered heterocyclic ring may have one or more halogen atoms).
[Aspect 3] In the compound of the present invention, G is a benzene ring (the benzene ring may have one or more fluorine atoms), X is a single bond or NR 6 , and Q is an oxygen atom, NH Or N-CN, Y is a C3-C6 cycloalkyl group optionally having one or more halogen atoms, CR 8 R 9 R 10 or NR 11 R 12 , and R 6 is one or more halogen atoms A C1 to C6 alkyl group which may have one or more hydrogen atoms, and R 8 , R 9 and R 10 each independently have one or more halogen atoms, or a C1 to C6 alkyl group which may have one or more halogen atoms; R 11 and R 12 each independently represent a C 1 -C 6 alkyl group (wherein the C 1 -C 6 alkyl group is selected from the group consisting of a halogen atom, a C 3 -C 6 cycloalkyl group and a C 1 -C 6 alkoxy group May have one or more substituents. A C3-C6 alkynyl group optionally having one or more halogen atoms, a C3-C6 cycloalkyl group optionally having one or more halogen atoms, or a hydrogen atom, or R 11 And R 12 combine with each other to form a 3- to 6-membered heterocyclic ring (wherein the 3- to 6-membered heterocyclic ring may have one or more halogen atoms), and A represents an oxadiazole ring. Compounds that bind to the para or meta position with respect to each other.
[Aspect 4] In the compound of the present invention, G is a benzene ring (the benzene ring may have one or more fluorine atoms), X is a single bond or NR 6 , and Q is an oxygen atom, NH Or N-CN, Y is a C3-C6 cycloalkyl group optionally having one or more halogen atoms, CR 8 R 9 R 10 or NR 11 R 12 , and R 6 is one or more halogen atoms A C1 to C6 alkyl group which may have one or more hydrogen atoms, and R 8 , R 9 and R 10 each independently have one or more halogen atoms. Or a hydrogen atom, each of R 11 and R 12 independently being a C 1 -C 6 alkyl group (wherein the C 1 -C 6 alkyl group is a halogen atom, a C 3 -C 6 cycloalkyl group and a C 1 -C 6 alkoxy group Even if it has one or more substituents selected Or a C3-C6 alkynyl group optionally having one or more halogen atoms, a C3-C6 cycloalkyl group optionally having one or more halogen atoms, or a hydrogen atom, or R 11 And R 12 combine with each other to form a 3- to 6-membered heterocyclic ring (wherein the 3- to 6-membered heterocyclic ring may have one or more halogen atoms), and A represents an oxadiazole ring. Compounds that bind to or in the para position.
[Aspect 5] In the compound of the present invention, G is a benzene ring, m is 0, X is a single bond or NR 6 , Q is an oxygen atom, n is 2 and Y is C 3 -C 6 It is a cycloalkyl group, CR 8 R 9 R 10 or NR 11 R 12 and R 6 is a C1-C6 alkyl group optionally having one or more halogen atoms, C3-C6 alkynyl group, C3-C6 cycloalkyl R 8 , R 9 and R 10 each independently represent a C 1 -C 6 alkyl group or a hydrogen atom, and R 11 and R 12 each independently represent a C 1 -C 6 alkyl Compounds wherein A is attached to the benzene ring in a para-position to the oxadiazole ring;
[Aspect 6] In the compound of the present invention, G is a benzene ring, m is 0, X is a single bond or NR 6 , Q is an oxygen atom, n is 2 and Y is C3-C6. It is a cycloalkyl group or CR 8 R 9 R 10 , and R 6 is a C 1 to C 6 alkyl group optionally having one or more halogen atoms, a C 3 to C 6 alkynyl group, a C 3 to C 6 cycloalkyl group, or a hydrogen atom Compounds wherein R 8 , R 9 and R 10 are each independently a C 1 -C 6 alkyl group or a hydrogen atom, and A is bonded on the benzene ring in the para-position to the oxadiazole ring.

[態様7] 本発明化合物において、Xが単結合であり、Qが酸素原子、NH又はN−CNであり、Gが1以上のフッ素原子を有していてもよいベンゼン環であり、Yが1以上のハロゲン原子を有していてもよいC3−C6シクロアルキル基又はCR8910である化合物。
[態様8] 本発明化合物において、Xが単結合であり、Qが酸素原子、NH又はN−CNであり、Gが1以上のフッ素原子を有していてもよいベンゼン環であり、Yが1以上のハロゲン原子を有していてもよいC3−C6シクロアルキル基又はCR8910であり、Aがオキサジアゾール環に対してパラ位又はメタ位に結合する化合物。
[態様9] 本発明化合物において、Xが単結合であり、Qが酸素原子、NH又はN−CNであり、Gが1以上のフッ素原子を有していてもよいベンゼン環であり、Yが1以上のハロゲン原子を有していてもよいC3−C6シクロアルキル基又はCR8910であり、R8、R9及びR10が各々独立して、1以上のハロゲン原子を有していてもよいC1−C6アルキル基又は水素原子であり、Aがオキサジアゾール環に対してパラ位又はメタ位に結合する化合物。
[態様10] 本発明化合物において、Xが単結合であり、Qが酸素原子、NH又はN−CNであり、Gが1以上のフッ素原子を有していてもよいベンゼン環であり、Yが1以上のハロゲン原子を有していてもよいC3−C6シクロアルキル基又はCR8910であり、R8、R9及びR10が各々独立して、1以上のハロゲン原子を有していてもよいC1−C6アルキル基又は水素原子であり、Aがオキサジアゾール環に対してパラ位に結合する化合物。
[Aspect 7] In the compound of the present invention, X is a single bond, Q is an oxygen atom, NH or N-CN, G is a benzene ring optionally having one or more fluorine atoms, and Y is 1 or more halogen atoms have a C3-C6 cycloalkyl group or a CR 8 R 9 R 10 compounds wherein.
[Aspect 8] In the compound of the present invention, X is a single bond, Q is an oxygen atom, NH or N-CN, G is a benzene ring optionally having one or more fluorine atoms, and Y is A compound wherein C is a C3 to C6 cycloalkyl group optionally having one or more halogen atoms or CR 8 R 9 R 10 , and A is bonded to the para- or meta-position with respect to the oxadiazole ring.
[Aspect 9] In the compound of the present invention, X is a single bond, Q is an oxygen atom, NH or N-CN, G is a benzene ring optionally having one or more fluorine atoms, and Y is It is a C3-C6 cycloalkyl group which may have one or more halogen atoms or CR 8 R 9 R 10 , and R 8 , R 9 and R 10 each independently have one or more halogen atoms. A compound wherein the C is a C1 to C6 alkyl group or a hydrogen atom, and A is bonded to the para or meta position with respect to the oxadiazole ring.
[Aspect 10] In the compound of the present invention, X is a single bond, Q is an oxygen atom, NH or N-CN, G is a benzene ring optionally having one or more fluorine atoms, and Y is It is a C3-C6 cycloalkyl group which may have one or more halogen atoms or CR 8 R 9 R 10 , and R 8 , R 9 and R 10 each independently have one or more halogen atoms. A compound wherein the C is a C1 to C6 alkyl group or a hydrogen atom, and A is bonded to a position para to the oxadiazole ring.

[態様11] 本発明化合物において、Xが単結合であり、Qが酸素原子、NH又はN−CNであり、Gが1以上のフッ素原子を有していてもよいベンゼン環であり、YがCR8910であり、R8、R9及びR10が各々独立して、1以上のハロゲン原子を有していてもよいC1−C6アルキル基又は水素原子であり、Aがオキサジアゾール環に対してパラ位又はメタ位に結合する化合物。
[態様12] 本発明化合物において、Xが単結合であり、Qが酸素原子、NH又はN−CNであり、Gがベンゼン環であり、YがCR8910であり、R8、R9及びR10が各々独立して、C1−C6アルキル基又は水素原子であり、Aがオキサジアゾール環に対してパラ位又はメタ位に結合する化合物。
[態様13] 本発明化合物において、Xが単結合であり、Qが酸素原子であり、Gがベンゼン環であり、YがCR8910であり、R8、R9及びR10が各々独立して、C1−C6アルキル基又は水素原子であり、Aがオキサジアゾール環に対してパラ位又はメタ位に結合する化合物。
[態様14] 本発明化合物において、Xが単結合であり、Qが酸素原子、NH又はN−CNであり、Gが1以上のフッ素原子を有していてもよいベンゼン環であり、YがCR8910であり、R8、R9及びR10が各々独立して、1以上のハロゲン原子を有していてもよいC1−C6アルキル基又は水素原子であり、Aがオキサジアゾール環に対してパラ位に結合する化合物。
[Aspect 11] In the compound of the present invention, X is a single bond, Q is an oxygen atom, NH or N-CN, G is a benzene ring optionally having one or more fluorine atoms, and Y is R 8 R 9 R 10 , each of R 8 , R 9 and R 10 independently being a C 1 -C 6 alkyl group optionally having one or more halogen atoms or a hydrogen atom; A compound bound in the para or meta position to the azole ring.
[Aspect 12] In the compound of the present invention, X is a single bond, Q is an oxygen atom, NH or N—CN, G is a benzene ring, Y is CR 8 R 9 R 10 , R 8 , Compounds wherein R 9 and R 10 are each independently a C 1 -C 6 alkyl group or a hydrogen atom, and A is bonded in the para- or meta-position to the oxadiazole ring.
[Aspect 13] In the compound of the present invention, X is a single bond, Q is an oxygen atom, G is a benzene ring, Y is CR 8 R 9 R 10 , and R 8 , R 9 and R 10 are Compounds each of which is independently a C1 to C6 alkyl group or a hydrogen atom, and wherein A is bonded to the para- or meta-position to the oxadiazole ring.
Embodiment 14 In the compound of the present invention, X is a single bond, Q is an oxygen atom, NH or N-CN, G is a benzene ring optionally having one or more fluorine atoms, and Y is R 8 R 9 R 10 , each of R 8 , R 9 and R 10 independently being a C 1 -C 6 alkyl group optionally having one or more halogen atoms or a hydrogen atom; A compound bound in the para-position to the azole ring.

[態様15] 本発明化合物において、Xが単結合であり、Qが酸素原子、NH又はN−CNであり、Gが1以上のフッ素原子を有していてもよいベンゼン環であり、YがCR8910であり、R8、R9及びR10が各々独立して、C1−C6アルキル基又は水素原子であり、Aがオキサジアゾール環に対してパラ位に結合する化合物。
[態様16] 本発明化合物において、Xが単結合であり、Qが酸素原子、NH又はN−CNであり、Gがベンゼン環であり、YがCR8910であり、R8、R9及びR10が各々独立して、C1−C6アルキル基又は水素原子であり、Aがオキサジアゾール環に対してパラ位に結合する化合物。
[態様17] 本発明化合物において、Xが単結合であり、Qが酸素原子であり、Gがベンゼン環であり、YがCR8910であり、R8、R9及びR10が各々独立して、C1−C6アルキル基又は水素原子であり、Aがオキサジアゾール環に対してパラ位に結合する化合物。
[Aspect 15] In the compound of the present invention, X is a single bond, Q is an oxygen atom, NH or N-CN, G is a benzene ring optionally having one or more fluorine atoms, and Y is a CR 8 R 9 R 10, independently R 8, R 9 and R 10 are each a C1-C6 alkyl group or a hydrogen atom, the compound a is attached at the para-position to the oxadiazole ring.
Embodiment 16 In the compound of the present invention, X is a single bond, Q is an oxygen atom, NH or N—CN, G is a benzene ring, Y is CR 8 R 9 R 10 , R 8 , Compounds wherein R 9 and R 10 are each independently a C 1 -C 6 alkyl group or a hydrogen atom, and A is bonded in the para-position to the oxadiazole ring.
[Aspect 17] In the compound of the present invention, X is a single bond, Q is an oxygen atom, G is a benzene ring, Y is CR 8 R 9 R 10 , R 8 , R 9 and R 10 are Each independently, a compound which is a C1-C6 alkyl group or a hydrogen atom, and in which A is bonded in the para-position to the oxadiazole ring.

[態様18] 本発明化合物において、Gが1以上のフッ素原子を有していてもよいベンゼン環であり、XがNR6であり、nが2であり、Qが酸素原子であり、Yが1以上のハロゲン原子を有していてもよいC3−C6シクロアルキル基又はCR8910である化合物。
[態様19] 本発明化合物において、Gがベンゼン環であり、XがNR6であり、nが2であり、Qが酸素原子であり、Yが1以上のハロゲン原子を有していてもよいC3−C6シクロアルキル基又はCR8910であり、Aがオキサジアゾール環に対してパラ位又はメタ位に結合する化合物。
[態様20] 本発明化合物において、Gがベンゼン環であり、XがNR6であり、R6が1以上のハロゲン原子を有していてもよいC1−C6アルキル基又は水素原子であり、nが2であり、Qが酸素原子であり、Yが1以上のハロゲン原子を有していてもよいC3−C6シクロアルキル基又はCR8910であり、R8、R9及びR10が各々独立して、1以上のハロゲン原子を有していてもよいC1−C6アルキル基、C3−C6アルキニル基又は水素原子であり、Aがオキサジアゾール環に対してパラ位又はメタ位に結合する化合物。
[態様21] 本発明化合物において、Gがベンゼン環であり、XがNR6であり、R6がC1−C6アルキル基又は水素原子であり、nが2であり、Qが酸素原子であり、YがC3−C6シクロアルキル基又はCR8910であり、R8、R9及びR10が各々独立して、C1−C6アルキル基、C3−C6アルキニル基又は水素原子であり、Aがオキサジアゾール環に対してパラ位又はメタ位に結合する化合物。
Embodiment 18 In the compound of the present invention, G is a benzene ring optionally having one or more fluorine atoms, X is NR 6 , n is 2 and Q is an oxygen atom, and Y is 1 or more halogen atoms have a C3-C6 cycloalkyl group or a CR 8 R 9 R 10 compounds wherein.
[Aspect 19] In the compound of the present invention, G may be a benzene ring, X may be NR 6 , n may be 2, Q may be an oxygen atom, and Y may have one or more halogen atoms. A compound wherein C is a C3-C6 cycloalkyl group or CR 8 R 9 R 10 and A is bonded to the para- or meta-position to the oxadiazole ring.
[Aspect 20] In the compound of the present invention, G is a benzene ring, X is NR 6 , and R 6 is a C1-C6 alkyl group optionally having one or more halogen atoms or a hydrogen atom, n Is 2, C is an oxygen atom, and Y is a C3-C6 cycloalkyl group optionally having one or more halogen atoms, or CR 8 R 9 R 10 , R 8 , R 9 and R 10 Each independently represents a C1 to C6 alkyl group optionally having one or more halogen atoms, a C3 to C6 alkynyl group, or a hydrogen atom, and A is in the para or meta position with respect to the oxadiazole ring The compound to bind.
[Aspect 21] In the compound of the present invention, G is a benzene ring, X is NR 6 , R 6 is a C1-C6 alkyl group or a hydrogen atom, n is 2 and Q is an oxygen atom, Y is a C3-C6 cycloalkyl group or CR 8 R 9 R 10 , and R 8 , R 9 and R 10 are each independently a C 1 -C 6 alkyl group, a C 3 -C 6 alkynyl group or a hydrogen atom, The compound which is attached to the para- or meta-position to the oxadiazole ring.

[態様22] 本発明化合物において、Gがベンゼン環であり、XがNR6であり、R6がC1−C6アルキル基又は水素原子であり、nが2であり、Qが酸素原子であり、YがC3−C6シクロアルキル基又はCR8910であり、R8、R9及びR10が各々独立して、C1−C6アルキル基、C3−C6アルキニル基又は水素原子であり、Aがオキサジアゾール環に対してパラ位に結合する化合物。
[態様23] 本発明化合物において、Gがベンゼン環であり、XがNR6であり、R6がC1−C6アルキル基又は水素原子であり、nが2であり、Qが酸素原子であり、YがC3−C6シクロアルキル基又はCR8910であり、R8、R9及びR10が各々独立して、C1−C6アルキル基、C3−C6アルキニル基又は水素原子であり、Aがオキサジアゾール環に対してメタ位に結合する化合物。
[態様24] 本発明化合物において、Gがベンゼン環であり、XがNR6であり、R6がC1−C6アルキル基又は水素原子であり、nが2であり、Qが酸素原子であり、YがC3−C6シクロアルキル基又はCR8910であり、R8、R9及びR10が各々独立して、C1−C6アルキル基又は水素原子であり、Aがオキサジアゾール環に対してパラ位に結合する化合物。
[態様25] 本発明化合物において、Gがベンゼン環であり、XがNR6であり、R6がC1−C6アルキル基又は水素原子であり、nが2であり、Qが酸素原子であり、YがC3−C6シクロアルキル基又はCR8910であり、R8、R9及びR10が各々独立して、C1−C6アルキル基又は水素原子であり、Aがオキサジアゾール環に対してメタ位に結合する化合物。
[態様26] 本発明化合物において、Gがベンゼン環であり、XがNR6であり、R6が1以上のハロゲン原子に置換されていてもよいC1−C6アルキル基、C3−C6アルキニル基、C3−C6シクロアルキル基又は水素原子であり、nが2であり、Qが酸素原子であり、YがC3−C6シクロアルキル基又はCR8910であり、R8、R9及びR10が各々独立して、C1−C6アルキル基又は水素原子であり、Aがベンゼン環上でオキサジアゾール環に対してパラ位に結合する化合物。
[態様27] 本発明化合物において、Gがベンゼン環であり、XがNR6であり、R6が1以上のハロゲン原子に置換されていてもよいC1−C6アルキル基、C3−C6アルキニル基、C3−C6シクロアルキル基又は水素原子であり、nが2であり、Qが酸素原子であり、YがCR8910であり、R8、R9及びR10が各々独立して、C1−C6アルキル基又は水素原子であり、Aがベンゼン環上でオキサジアゾール環に対してパラ位に結合する化合物。
Embodiment 22 In the compound of the present invention, G is a benzene ring, X is NR 6 , R 6 is a C1-C6 alkyl group or a hydrogen atom, n is 2 and Q is an oxygen atom, Y is a C3-C6 cycloalkyl group or CR 8 R 9 R 10 , and R 8 , R 9 and R 10 are each independently a C 1 -C 6 alkyl group, a C 3 -C 6 alkynyl group or a hydrogen atom, A compound in which p is bonded to the para position relative to the oxadiazole ring.
[Aspect 23] In the compound of the present invention, G is a benzene ring, X is NR 6 , R 6 is a C1-C6 alkyl group or a hydrogen atom, n is 2 and Q is an oxygen atom, Y is a C3-C6 cycloalkyl group or CR 8 R 9 R 10 , and R 8 , R 9 and R 10 are each independently a C 1 -C 6 alkyl group, a C 3 -C 6 alkynyl group or a hydrogen atom, A compound in which is attached to the meta position relative to the oxadiazole ring.
Embodiment 24 In the compound of the present invention, G is a benzene ring, X is NR 6 , R 6 is a C1-C6 alkyl group or a hydrogen atom, n is 2 and Q is an oxygen atom, Y is a C3-C6 cycloalkyl group or CR 8 R 9 R 10 , R 8 , R 9 and R 10 are each independently a C 1 -C 6 alkyl group or a hydrogen atom, and A is an oxadiazole ring Compounds that bind to the para position relative to each other.
Embodiment 25 In the compound of the present invention, G is a benzene ring, X is NR 6 , R 6 is a C1-C6 alkyl group or a hydrogen atom, n is 2 and Q is an oxygen atom, Y is a C3-C6 cycloalkyl group or CR 8 R 9 R 10 , R 8 , R 9 and R 10 are each independently a C 1 -C 6 alkyl group or a hydrogen atom, and A is an oxadiazole ring Compounds that bind to the meta position relative to each other.
Embodiment 26 In the compound of the present invention, C 1 -C 6 alkyl group, C 3 -C 6 alkynyl group, wherein G is a benzene ring, X is NR 6 and R 6 is optionally substituted by one or more halogen atoms, A C3-C6 cycloalkyl group or a hydrogen atom, n is 2, Q is an oxygen atom, Y is a C3-C6 cycloalkyl group or CR 8 R 9 R 10 , R 8 , R 9 and R 10. A compound wherein each of 10 is independently a C1 to C6 alkyl group or a hydrogen atom, and A is bonded to the benzene ring in a para-position to the oxadiazole ring.
Embodiment 27 In the compound of the present invention, C 1 -C 6 alkyl group, C 3 -C 6 alkynyl group, wherein G is a benzene ring, X is NR 6 and R 6 is optionally substituted by one or more halogen atoms, A C3-C6 cycloalkyl group or a hydrogen atom, n is 2, Q is an oxygen atom, Y is CR 8 R 9 R 10 , and R 8 , R 9 and R 10 are each independently A compound which is a C1-C6 alkyl group or a hydrogen atom, and in which A is bonded to the benzene ring in a para-position to the oxadiazole ring.

[態様28] 本発明化合物において、Gが1以上のフッ素原子を有していてもよいベンゼン環であり、Xが単結合であり、nが2であり、Qが酸素原子であり、YがNR1112である化合物。
[態様29] 本発明化合物において、Gが1以上のフッ素原子を有していてもよいベンゼン環であり、Xが単結合であり、nが2であり、Qが酸素原子であり、YがNR1112であり、R11及びR12が、各々独立して、C1−C6アルキル基(該C1−C6アルキル基は、ハロゲン原子、C3−C6シクロアルキル基及びC1−C6アルコキシ基からなる群より選ばれる1以上の置換基を有していてもよい)、1以上のハロゲン原子を有していてもよいC3−C6アルキニル基、1以上のハロゲン原子を有していてもよいC3−C6シクロアルキル基、若しくは水素原子であるか、又はR11とR12とが互いに結合して3−6員ヘテロ環(該3−6員ヘテロ環は1以上のハロゲン原子を有していてもよい)を形成しており、Aがオキサジアゾール環に対してパラ位又はメタ位に結合する化合物。
[態様30] 本発明化合物において、Gが1以上のフッ素原子を有していてもよいベンゼン環であり、Xが単結合であり、nが2であり、Qが酸素原子であり、YがNR1112であり、R11及びR12が、各々独立して、C1−C6アルキル基(該C1−C6アルキル基はC3−C6シクロアルキル基及びC1−C6アルコキシ基からなる群より選ばれる1以上の置換基を有していてもよい)、C3−C6アルキニル基、C3−C6シクロアルキル基、若しくは水素原子であるか、又はR11とR12とが互いに結合して3−6員ヘテロ環(該3−6員ヘテロ環は1以上のハロゲン原子を有していてもよい)を形成しており、Aがオキサジアゾール環に対してパラ位又はメタ位に結合する化合物。
[態様31] 本発明化合物において、Gが1以上のフッ素原子を有していてもよいベンゼン環であり、Xが単結合であり、nが2であり、Qが酸素原子であり、YがNR1112であり、R11及びR12が、各々独立して、C1−C6アルキル基(該C1−C6アルキル基はC3−C6シクロアルキル基及びC1−C6アルコキシ基からなる群より選ばれる1以上の置換基を有していてもよい)、C3−C6アルキニル基、C3−C6シクロアルキル基、若しくは水素原子であるか、又はR11とR12とが互いに結合して3−6員ヘテロ環(該3−6員ヘテロ環は1以上のハロゲン原子を有していてもよい)を形成しており、Aがオキサジアゾール環に対してパラ位に結合する化合物。
Embodiment 28 In the compound of the present invention, G is a benzene ring which may have one or more fluorine atoms, X is a single bond, n is 2, Q is an oxygen atom, and Y is The compound which is NR 11 R 12
Embodiment 29 In the compound of the present invention, G is a benzene ring which may have one or more fluorine atoms, X is a single bond, n is 2, Q is an oxygen atom, and Y is NR 11 R 12 wherein R 11 and R 12 each independently represent a C 1 -C 6 alkyl group (wherein the C 1 -C 6 alkyl group comprises a halogen atom, a C 3 -C 6 cycloalkyl group and a C 1 -C 6 alkoxy group C3-C6 alkynyl group optionally having one or more halogen atoms, C3-C6 alkynyl group optionally having one or more halogen atoms, and C3-C3 optionally having one or more halogen atoms A C6 cycloalkyl group, or a hydrogen atom, or R 11 and R 12 are bonded to each other to form a 3- to 6-membered heterocyclic ring (the 3- to 6-membered heterocyclic ring may have one or more halogen atoms Good), and A is oxadiazo Compounds that bind to the para or meta position relative to the Le ring.
[Aspect 30] In the compound of the present invention, G is a benzene ring which may have one or more fluorine atoms, X is a single bond, n is 2, Q is an oxygen atom, and Y is NR 11 R 12 wherein R 11 and R 12 are each independently a C 1 -C 6 alkyl group (wherein the C 1 -C 6 alkyl group is selected from the group consisting of a C 3 -C 6 cycloalkyl group and a C 1 -C 6 alkoxy group And C 3 -C 6 alkynyl group, C 3 -C 6 cycloalkyl group, or a hydrogen atom, or R 11 and R 12 are bonded to each other to form 3 to 6 members A compound which forms a hetero ring (wherein the 3- to 6-membered hetero ring may have one or more halogen atoms) and A bonds to the para- or meta-position with respect to the oxadiazole ring.
In the compound of the present invention, G is a benzene ring optionally having one or more fluorine atoms, X is a single bond, n is 2, Q is an oxygen atom, and Y is NR 11 R 12 wherein R 11 and R 12 are each independently a C 1 -C 6 alkyl group (wherein the C 1 -C 6 alkyl group is selected from the group consisting of a C 3 -C 6 cycloalkyl group and a C 1 -C 6 alkoxy group And C 3 -C 6 alkynyl group, C 3 -C 6 cycloalkyl group, or a hydrogen atom, or R 11 and R 12 are bonded to each other to form 3 to 6 members A compound which forms a heterocyclic ring (wherein the 3- to 6-membered heterocyclic ring may have one or more halogen atoms), and wherein A is bonded in the para-position to the oxadiazole ring.

[態様32] 本発明化合物において、Gが1以上のフッ素原子を有していてもよいベンゼン環であり、Xが単結合であり、nが2であり、Qが酸素原子であり、YがNR1112であり、R11及びR12が、各々独立して、C1−C6アルキル基(該C1−C6アルキル基はC3−C6シクロアルキル基及びC1−C6アルコキシ基からなる群より選ばれる1以上の置換基を有していてもよい)、C3−C6アルキニル基、C3−C6シクロアルキル基、若しくは水素原子であるか、又はR11とR12とが互いに結合して3−6員ヘテロ環(該3−6員ヘテロ環は1以上のハロゲン原子を有していてもよい)を形成しており、Aがオキサジアゾール環に対してメタ位に結合する化合物。
[態様33] 本発明化合物において、Gが1以上のフッ素原子を有していてもよいベンゼン環であり、Xが単結合であり、nが2であり、Qが酸素原子であり、YがNR1112であり、R11及びR12が、各々独立してC1−C6アルキル基(該C1−C6アルキル基はC3−C6シクロアルキル基及びC1−C6アルコキシ基からなる群より選ばれる1以上の置換基を有していてもよい)、C3−C6アルキニル基、C3−C6シクロアルキル基、若しくは水素原子であるか、又はR11とR12とが互いに結合して3−6員ヘテロ環を形成しており、Aがオキサジアゾール環に対してパラ位又はメタ位に結合する化合物。
[態様34] 本発明化合物において、Gが1以上のフッ素原子を有していてもよいベンゼン環であり、Xが単結合であり、nが2であり、Qが酸素原子であり、YがNR1112であり、R11及びR12が、各々独立して、C1−C6アルキル基(該C1−C6アルキル基はC3−C6シクロアルキル基及びC1−C6アルコキシ基からなる群より選ばれる1以上の置換基を有していてもよい)、C3−C6アルキニル基、C3−C6シクロアルキル基、若しくは水素原子であるか、又はR11とR12とが互いに結合して3−6員ヘテロ環を形成しており、Aがオキサジアゾール環に対してパラ位に結合する化合物。
[態様35] 本発明化合物において、Gが1以上のフッ素原子を有していてもよいベンゼン環であり、Xが単結合であり、nが2であり、Qが酸素原子であり、YがNR1112であり、R11及びR12が、各々独立して、C1−C6アルキル基(該C1−C6アルキル基はC3−C6シクロアルキル基及びC1−C6アルコキシ基からなる群より選ばれる1以上の置換基を有していてもよい)、C3−C6アルキニル基、C3−C6シクロアルキル基、若しくは水素原子であるか、又はR11とR12とが互いに結合して3−6員ヘテロ環を形成しており、Aがオキサジアゾール環に対してメタ位に結合する化合物。
Embodiment 32 In the compound of the present invention, G is a benzene ring optionally having one or more fluorine atoms, X is a single bond, n is 2, Q is an oxygen atom, and Y is NR 11 R 12 wherein R 11 and R 12 are each independently a C 1 -C 6 alkyl group (wherein the C 1 -C 6 alkyl group is selected from the group consisting of a C 3 -C 6 cycloalkyl group and a C 1 -C 6 alkoxy group And C 3 -C 6 alkynyl group, C 3 -C 6 cycloalkyl group, or a hydrogen atom, or R 11 and R 12 are bonded to each other to form 3 to 6 members A compound which forms a hetero ring (wherein the 3- to 6-membered hetero ring may have one or more halogen atoms), and A bonds to the meta position with respect to the oxadiazole ring.
[Aspect 33] In the compound of the present invention, G is a benzene ring optionally having one or more fluorine atoms, X is a single bond, n is 2, Q is an oxygen atom, and Y is NR 11 R 12 , each of R 11 and R 12 independently being a C 1 -C 6 alkyl group (wherein the C 1 -C 6 alkyl group is selected from the group consisting of a C 3 -C 6 cycloalkyl group and a C 1 -C 6 alkoxy group Or C 3 -C 6 alkynyl group, C 3 -C 6 cycloalkyl group, or a hydrogen atom, or R 11 and R 12 are bonded to each other to form a 3- to 6-membered hetero ring Compounds which form a ring and in which A is bonded to the para- or meta-position to the oxadiazole ring.
[Aspect 34] In the compound of the present invention, G is a benzene ring optionally having one or more fluorine atoms, X is a single bond, n is 2, Q is an oxygen atom, and Y is NR 11 R 12 wherein R 11 and R 12 are each independently a C 1 -C 6 alkyl group (wherein the C 1 -C 6 alkyl group is selected from the group consisting of a C 3 -C 6 cycloalkyl group and a C 1 -C 6 alkoxy group And C 3 -C 6 alkynyl group, C 3 -C 6 cycloalkyl group, or a hydrogen atom, or R 11 and R 12 are bonded to each other to form 3 to 6 members A compound which forms a hetero ring and in which A is bonded in the para-position to the oxadiazole ring.
[Aspect 35] In the compound of the present invention, G is a benzene ring which may have one or more fluorine atoms, X is a single bond, n is 2, Q is an oxygen atom, and Y is NR 11 R 12 wherein R 11 and R 12 are each independently a C 1 -C 6 alkyl group (wherein the C 1 -C 6 alkyl group is selected from the group consisting of a C 3 -C 6 cycloalkyl group and a C 1 -C 6 alkoxy group And C 3 -C 6 alkynyl group, C 3 -C 6 cycloalkyl group, or a hydrogen atom, or R 11 and R 12 are bonded to each other to form 3 to 6 members A compound which forms a hetero ring and in which A is bonded to a meta position with respect to the oxadiazole ring.

[態様36] 本発明化合物において、Gが1以上のフッ素原子を有していてもよいベンゼン環であり、Xが単結合であり、nが2であり、Qが酸素原子であり、YがNR1112であり、R11及びR12が、各々独立して、C1−C6アルキル基(該C1−C6アルキル基はC3−C6シクロアルキル基及びC1−C6アルコキシ基からなる群より選ばれる1以上の置換基を有していてもよい)、C3−C6アルキニル基、C3−C6シクロアルキル基又は水素原子であり、Aがオキサジアゾール環に対してパラ位に結合する化合物。
[態様37] 本発明化合物において、Gがベンゼン環であり、Xが単結合であり、nが2であり、Qが酸素原子であり、YがNR1112であり、R11及びR12が、各々独立して、C1−C6アルキル基(該C1−C6アルキル基はC3−C6シクロアルキル基及びC1−C6アルコキシ基からなる群より選ばれる1以上の置換基を有していてもよい)、C3−C6アルキニル基、C3−C6シクロアルキル基又は水素原子であり、Aがオキサジアゾール環に対してパラ位に結合する化合物。
[態様38] 本発明化合物において、Gが1以上のフッ素原子を有していてもよいベンゼン環であり、Xが単結合であり、nが2であり、Qが酸素原子であり、YがNR1112であり、R11及びR12が、各々独立して、1以上のC3−C6シクロアルキル基を有していてもよいC1−C6アルキル基、若しくは水素原子であるか、又はR11とR12とが互いに結合して3−6員ヘテロ環を形成しており、Aがオキサジアゾール環に対してパラ位に結合する化合物。
[態様39] 本発明化合物において、Gがベンゼン環であり、Xが単結合であり、nが2であり、Qが酸素原子であり、YがNR1112であり、R11及びR12が、各々独立して、1以上のC3−C6シクロアルキル基を有していてもよいC1−C6アルキル基、若しくは水素原子であるか、又はR11とR12とが互いに結合して3−6員ヘテロ環を形成しており、Aがオキサジアゾール環に対してパラ位に結合する化合物。
Embodiment 36 In the compound of the present invention, G is a benzene ring optionally having one or more fluorine atoms, X is a single bond, n is 2, Q is an oxygen atom, and Y is NR 11 R 12 wherein R 11 and R 12 are each independently a C 1 -C 6 alkyl group (wherein the C 1 -C 6 alkyl group is selected from the group consisting of a C 3 -C 6 cycloalkyl group and a C 1 -C 6 alkoxy group A compound which is optionally substituted with one or more substituents, a C3 to C6 alkynyl group, a C3 to C6 cycloalkyl group or a hydrogen atom, and wherein A is bonded to the para-position to the oxadiazole ring.
Embodiment 37 In the compound of the present invention, G is a benzene ring, X is a single bond, n is 2, Q is an oxygen atom, Y is NR 11 R 12 , R 11 and R 12. Each independently represents a C1-C6 alkyl group (the C1-C6 alkyl group may have one or more substituents selected from the group consisting of a C3-C6 cycloalkyl group and a C1-C6 alkoxy group And a) a C3 to C6 alkynyl group, a C3 to C6 cycloalkyl group, or a hydrogen atom, wherein A is bonded to a position para to an oxadiazole ring.
[Aspect 38] In the compound of the present invention, G is a benzene ring which may have one or more fluorine atoms, X is a single bond, n is 2, Q is an oxygen atom, and Y is a NR 11 R 12, R 11 and R 12 are each independently one or more C3-C6 cycloalkyl group optionally may C1-C6 alkyl group which may have, or is a hydrogen atom, or R Compounds in which 11 and R 12 are bonded to each other to form a 3- to 6-membered heterocyclic ring, and A is bonded in the para-position to the oxadiazole ring.
Embodiment 39 In the compound of the present invention, G is a benzene ring, X is a single bond, n is 2, Q is an oxygen atom, Y is NR 11 R 12 , R 11 and R 12. Each independently represents a C1-C6 alkyl group optionally having one or more C3-C6 cycloalkyl groups, or a hydrogen atom, or R 11 and R 12 are bonded to each other to form 3- Compounds which form a 6-membered heterocyclic ring and in which A is bonded to the oxadiazole ring in the para position.

[態様40] 本発明化合物において、Gが1以上のフッ素原子を有していてもよいベンゼン環であり、Xが単結合であり、nが2であり、Qが酸素原子であり、YがNR1112であり、R11及びR12が、各々独立して、1以上のC3−C6シクロアルキル基を有していてもよいC1−C6アルキル基又は水素原子であり、Aがオキサジアゾール環に対してパラ位に結合する化合物。
[態様41] 本発明化合物において、Gがベンゼン環であり、Xが単結合であり、nが2であり、Qが酸素原子であり、YがNR1112であり、R11及びR12が、各々独立して、1以上のC3−C6シクロアルキル基を有していてもよいC1−C6アルキル基又は水素原子であり、Aがオキサジアゾール環に対してパラ位に結合する化合物。
[Aspect 40] In the compound of the present invention, G is a benzene ring which may have one or more fluorine atoms, X is a single bond, n is 2, Q is an oxygen atom, and Y is a NR 11 R 12, R 11 and R 12 are each independently, 1 or more C3-C6 cycloalkyl group optionally may be C1-C6 alkyl group or a hydrogen atom has, a is Okisaji A compound bound in the para-position to the azole ring.
Embodiment 41 In the compound of the present invention, G is a benzene ring, X is a single bond, n is 2, Q is an oxygen atom, Y is NR 11 R 12 , R 11 and R 12. And each is independently a C1 to C6 alkyl group optionally having one or more C3 to C6 cycloalkyl groups or a hydrogen atom, wherein A is bonded to the para-position to the oxadiazole ring.

[態様42] 本発明化合物において、Xが単結合であり、Qが酸素原子であり、Gがべンゼン環であり、R2及びR3が水素原子であり、YがCR8910であり、R8、R9及びR10が各々独立して、C1−C6アルキル基又は水素原子であり、Aがオキサジアゾール環に対してパラ位又はメタ位に結合する化合物。
[態様43] 本発明化合物において、Xが単結合であり、Qが酸素原子であり、Gがべンゼン環であり、R2及びR3が水素原子であり、YがCR8910であり、R8、R9及びR10が各々独立して、C1−C6アルキル基又は水素原子であり、Aがオキサジアゾール環に対してパラ位に結合する化合物。
[態様44] 本発明化合物において、Xが単結合であり、Qが酸素原子であり、Gがべンゼン環であり、R2及びR3が水素原子であり、YがCR8910であり、R8、R9及びR10が各々独立して、C1−C6アルキル基又は水素原子であり、Aがオキサジアゾール環に対してメタ位に結合する化合物。
Embodiment 42 In the compound of the present invention, X is a single bond, Q is an oxygen atom, G is a benzene ring, R 2 and R 3 are hydrogen atoms, and Y is CR 8 R 9 R 10 Compounds wherein R 8 , R 9 and R 10 are each independently a C 1 -C 6 alkyl group or a hydrogen atom, and A is bonded to the para- or meta-position with respect to the oxadiazole ring.
[Aspect 43] In the compound of the present invention, X is a single bond, Q is an oxygen atom, G is a benzene ring, R 2 and R 3 are hydrogen atoms, and Y is CR 8 R 9 R 10 Compounds wherein R 8 , R 9 and R 10 are each independently a C 1 -C 6 alkyl group or a hydrogen atom, and A is bonded in the para-position to the oxadiazole ring.
In the compound of the present invention, X is a single bond, Q is an oxygen atom, G is a benzene ring, R 2 and R 3 are hydrogen atoms, and Y is CR 8 R 9 R 10 Compounds wherein R 8 , R 9 and R 10 are each independently a C 1 -C 6 alkyl group or a hydrogen atom, and A is attached to the meta position with respect to the oxadiazole ring.

[態様45] 本発明化合物において、Xが単結合であり、Qが酸素原子であり、Gがベンゼン環又はピリジン環であり、YがCR8910であり、R8、R9及びR10が各々独立して、C1−C6アルキル基又は水素原子であり、Aがオキサジアゾール環に対してパラ位に結合する化合物。
[態様46] 本発明化合物において、Xが単結合であり、Qが酸素原子であり、Gがピリジン環であり、YがCR8910であり、R8、R9及びR10が各々独立して、C1−C6アルキル基又は水素原子であり、Aがオキサジアゾール環に対してパラ位に結合する化合物。
[Aspect 45] In the compound of the present invention, X is a single bond, Q is an oxygen atom, G is a benzene ring or a pyridine ring, Y is CR 8 R 9 R 10 , R 8 , R 9 and Compounds wherein each R 10 is independently a C 1 -C 6 alkyl group or a hydrogen atom, and A is bonded in the para-position to the oxadiazole ring;
[Aspect 46] In the compound of the present invention, X is a single bond, Q is an oxygen atom, G is a pyridine ring, Y is CR 8 R 9 R 10 , R 8 , R 9 and R 10 are Each independently, a compound which is a C1-C6 alkyl group or a hydrogen atom, and in which A is bonded in the para-position to the oxadiazole ring.

[態様47] 本発明化合物において、Xが単結合であり、Qが酸素原子、NH又はN−CNであり、Gがピリジン環であり、YがCR8910であり、R8、R9及びR10が各々独立して、C1−C6アルキル基又は水素原子であり、Aがオキサジアゾール環に対してパラ位に結合する化合物。
[態様48] 本発明化合物において、Xが単結合であり、Qが酸素原子、NH又はN−CNであり、Gがピリジン環であり、YがCR8910であり、R8、R9及びR10が各々独立して、C1−C6アルキル基又は水素原子であり、Aがオキサジアゾール環に対してメタ位に結合する化合物。
[態様49] 本発明化合物において、Xが単結合であり、Qが酸素原子であり、Gがピリジン環であり、YがCR8910であり、R8、R9及びR10が各々独立して、C1−C6アルキル基又は水素原子であり、Aがオキサジアゾール環に対してメタ位に結合する化合物。
[態様50] 本発明化合物において、Xが単結合であり、Qが酸素原子であり、nが2であり、Gがベンゼン環であり、Aがオキサジアゾール環に対してパラ位に結合する化合物。
[態様51] 本発明化合物において、Xが単結合であり、Qが酸素原子であり、nが2であり、Gがベンゼン環であり、YがCR8910であり、Aがオキサジアゾール環に対してパラ位に結合する化合物。
[態様52] 本発明化合物において、Xが単結合であり、Qが酸素原子であり、Gがベンゼン環であり、YがCR8910であり、R8、R9及びR10が水素原子であり、Aがオキサジアゾール環に対してパラ位に結合する化合物。
Embodiment 47 In the compound of the present invention, X is a single bond, Q is an oxygen atom, NH or N-CN, G is a pyridine ring, Y is CR 8 R 9 R 10 , R 8 , Compounds wherein R 9 and R 10 are each independently a C 1 -C 6 alkyl group or a hydrogen atom, and A is bonded in the para-position to the oxadiazole ring.
[Aspect 48] In the compound of the present invention, X is a single bond, Q is an oxygen atom, NH or N-CN, G is a pyridine ring, Y is CR 8 R 9 R 10 , R 8 , Compounds wherein R 9 and R 10 are each independently a C 1 -C 6 alkyl group or a hydrogen atom, and A is bonded to the meta position relative to the oxadiazole ring.
Embodiment 49 In the compound of the present invention, X is a single bond, Q is an oxygen atom, G is a pyridine ring, Y is CR 8 R 9 R 10 , R 8 , R 9 and R 10 are Each independently, a compound which is a C1-C6 alkyl group or a hydrogen atom, and in which A is bonded to a meta position with respect to the oxadiazole ring.
Embodiment 50 In the compound of the present invention, X is a single bond, Q is an oxygen atom, n is 2 and G is a benzene ring, and A is bonded to the para-position to the oxadiazole ring Compound.
In the compound of the present invention, X is a single bond, Q is an oxygen atom, n is 2, G is a benzene ring, Y is CR 8 R 9 R 10 , and A is oxa A compound bound in the para-position to the diazole ring.
Embodiment 52 In the compound of the present invention, X is a single bond, Q is an oxygen atom, G is a benzene ring, Y is CR 8 R 9 R 10 , and R 8 , R 9 and R 10 are A compound which is a hydrogen atom and in which A is bonded to the oxadiazole ring in the para position.

[態様53] 態様1〜52のいずれかにおいて、Aが単結合であり、mが0である化合物。
[態様54] 態様1〜52のいずれかにおいて、Aが酸素原子である化合物。
[態様55] 態様1〜52のいずれかにおいて、Aが酸素原子であり、mが1又は2である化合物。
[態様56] 態様1〜52のいずれかにおいて、Aが酸素原子であり、mが0である化合物。
[Aspect 53] The compound according to any of Aspects 1 to 52, wherein A is a single bond and m is 0.
ASPECT 54 The compound whose A is an oxygen atom in any one of aspects 1-52.
55. A compound according to any one of the preceding embodiments, wherein A is an oxygen atom and m is 1 or 2.
Embodiment 56 A compound according to any of Embodiments 1 to 52, wherein A is an oxygen atom and m is 0.

次に、本発明化合物の製造法について説明する。   Next, the process for producing the compound of the present invention is described.

本発明化合物は、以下の製造法等により製造することができる。   The compound of the present invention can be produced by the following production method and the like.

製造法A
本発明化合物は、式(A1)で示される化合物(以下、化合物(A1)と記す。)とトリフルオロ酢酸無水物とを塩基の存在下で反応させることにより製造することができる。

Figure 2019089711
〔式中、記号は前記と同じ意味を表す。〕
反応は、通常溶媒中で行われる。反応に用いられる溶媒としては、例えば、n−ヘキサン、シクロヘキサン、トルエン、キシレン等の炭化水素(以下、炭化水素類と記す。)、ジエチルエーテル、テトラヒドロフラン、1,4−ジオキサン、エチレングリコ−ルジメチルエ−テル、メチルtert−ブチルエーテル、ジイソプロピルエーテル等のエーテル(以下、エーテル類と記す。)、クロロホルム、ジクロロメタン、クロロベンゼン等のハロゲン化炭化水素(以下、ハロゲン化炭化水素類と記す。)、N,N−ジメチルホルムアミド、1,3−ジメチル−2−イミダゾリジノン、N−メチルピロリドン等のアミド(以下、アミド類と記す。)、酢酸エチル、酢酸メチル等のエステル(以下、エステル類と記す。)、ジメチルスルホキシド等のスルホキシド(以下、スルホキシド類と記す。)、アセトニトリル、プロピオニトリル等のニトリル(以下、ニトリル類と記す。)、水及びこれらの混合物が挙げられる。
反応に用いられる塩基としては例えば、トリエチルアミン、ピリジン、2,2’−ビピリジン、ジアザビシクロウンデセン等の有機塩基(以下、有機塩基類と記す。)、炭酸ナトリウム、炭酸カリウム等の炭酸塩(以下、炭酸塩類と記す。)、炭酸水素ナトリウム、炭酸水素カリウム等の炭酸水素塩(以下、炭酸水素塩類と記す)が挙げられる。
反応には、化合物(A1)1モルに対して、トリフルオロ酢酸無水物が通常1〜10モルの割合、塩基が通常1〜10モルの割合で用いられる。
反応温度は通常−20〜150℃の範囲内である。反応時間は通常0.1〜120時間の範囲内である。
反応終了後は、反応混合物を水と混合した後、有機溶媒で抽出し、有機層を、乾燥、濃縮等の後処理操作に付すことにより本発明化合物を単離することができる。また、反応混合物に水を添加し、析出物をろ取することにより本発明化合物を単離することもできる。 Production method A
The compound of the present invention can be produced by reacting a compound represented by the formula (A1) (hereinafter referred to as compound (A1)) with trifluoroacetic anhydride in the presence of a base.
Figure 2019089711
Wherein the symbols have the same meanings as described above. ]
The reaction is usually carried out in a solvent. Examples of the solvent used for the reaction include hydrocarbons such as n-hexane, cyclohexane, toluene and xylene (hereinafter referred to as hydrocarbons), diethyl ether, tetrahydrofuran, 1,4-dioxane, ethylene glycol dimethyl ether Ethers such as tellurium, methyl tert-butyl ether and diisopropyl ether (hereinafter referred to as ethers), halogenated hydrocarbons such as chloroform, dichloromethane and chlorobenzene (hereinafter referred to as halogenated hydrocarbons), N, N- Amides such as dimethylformamide, 1,3-dimethyl-2-imidazolidinone, N-methylpyrrolidone (hereinafter referred to as amides), esters such as ethyl acetate and methyl acetate (hereinafter referred to as esters), Sulfoxide such as dimethyl sulfoxide (hereinafter referred to as sulfo Referred to Sid class.), Acetonitrile, nitriles such as propionitrile (hereinafter, referred to as nitriles.) Water, and mixtures thereof.
Examples of the base used for the reaction include organic bases such as triethylamine, pyridine, 2,2'-bipyridine and diazabicycloundecene (hereinafter referred to as organic bases), carbonates such as sodium carbonate and potassium carbonate Hereinafter, it is described as carbonates), hydrogencarbonates such as sodium hydrogencarbonate and potassium hydrogencarbonate (hereinafter referred to as hydrogencarbonates).
In the reaction, 1 to 10 moles of trifluoroacetic anhydride are generally used, and 1 to 10 moles of a base are usually used, relative to 1 mole of the compound (A1).
The reaction temperature is usually in the range of -20 to 150 ° C. The reaction time is usually in the range of 0.1 to 120 hours.
After completion of the reaction, the reaction mixture is mixed with water and extracted with an organic solvent, and the organic layer is subjected to post-treatment operations such as drying and concentration to isolate the compound of the present invention. Alternatively, the compound of the present invention can be isolated by adding water to the reaction mixture and filtering the precipitate.

製造法B
式(1B)で示される化合物(以下、化合物(1B)と記す。)又は式(1C)で示される化合物(以下、化合物(1C)と記す。)は、式(1A)で示される化合物(以下、化合物(1A)と記す。)と酸化剤とを反応させることにより製造することができる。

Figure 2019089711
〔式中、記号は前記と同じ意味を表す。〕
反応は、通常溶媒中で行われる。反応に用いられる溶媒としては、炭化水素類、エーテル類、ハロゲン化炭化水素類、アミド類、エステル類、スルホキシド類、ニトリル類、アルコール、水及びこれらの混合物等が挙げられる。
反応に用いられる酸化剤としては、過酸化水素水、m−クロロ過安息香酸、過ヨウ素酸ナトリウム、過ヨウ素酸カリウム等が挙げられる。
反応には塩基を加えてもよく、塩基としては、炭酸ナトリウム、炭酸カリウム等のアルカリ金属炭酸塩が挙げられる。
反応には添加剤を加えてもよく、例えば、トリフルオロ酢酸、ルテニウム三塩化物・水和物が挙げられる。
化合物(1B)を製造する際、反応には、化合物(1A)1モルに対して、通常酸化剤が1〜1.9モルの割合、塩基が1〜10モルの割合、添加剤が0.01〜10モルの割合で用いられる。
化合物(1C)を製造する際、反応には、化合物(1A)1モルに対して、通常酸化剤が2〜10モルの割合、塩基が1〜10モルの割合、添加剤が0.01〜10モルの割合で用いられる。
反応温度は通常−20〜150℃の範囲内である。反応時間は通常0.1〜120時間の範囲内である。
反応終了後は、反応混合物を水と混合した後、有機溶媒で抽出し、有機層を、乾燥、濃縮等の後処理操作に付すことにより化合物(1B)又は化合物(1C)を単離することができる。また、シリカゲルクロマトグラフィー等により精製することができる。 Manufacturing method B
The compound represented by the formula (1B) (hereinafter referred to as the compound (1B)) or the compound represented by the formula (1C) (hereinafter referred to as the compound (1C)) is a compound represented by the formula (1A) Hereinafter, it can be produced by reacting the compound (1A) with an oxidizing agent.
Figure 2019089711
Wherein the symbols have the same meanings as described above. ]
The reaction is usually carried out in a solvent. Examples of the solvent used for the reaction include hydrocarbons, ethers, halogenated hydrocarbons, amides, esters, sulfoxides, nitriles, alcohols, water, and mixtures thereof.
As an oxidizing agent used for the reaction, hydrogen peroxide water, m-chloroperbenzoic acid, sodium periodate, potassium periodate and the like can be mentioned.
A base may be added to the reaction, and examples of the base include alkali metal carbonates such as sodium carbonate and potassium carbonate.
An additive may be added to the reaction, and examples thereof include trifluoroacetic acid and ruthenium trichloride hydrate.
In the production of compound (1B), the reaction is usually carried out in a proportion of 1 to 1.9 mol of an oxidizing agent, 1 to 10 mol of a base, 0.1 part of an additive or 1 part of a compound (1A). It is used in a proportion of 01 to 10 moles.
In producing the compound (1C), the reaction is usually carried out in a ratio of 2 to 10 moles of an oxidizing agent, 1 to 10 moles of a base, 0.01 to 1 mole of an additive, per 1 mole of the compound (1A) It is used at a rate of 10 moles.
The reaction temperature is usually in the range of -20 to 150 ° C. The reaction time is usually in the range of 0.1 to 120 hours.
After completion of the reaction, the reaction mixture is mixed with water and then extracted with an organic solvent, and the organic layer is subjected to post-treatment operations such as drying and concentration to isolate compound (1B) or compound (1C). Can. It can also be purified by silica gel chromatography or the like.

製造法C
式(1E)で示される化合物は、式(1D)で示される化合物と酸化剤とを反応させることにより製造することができる。反応は、製造法Bに記載の方法に準じて実施される。

Figure 2019089711
〔式中、Q1は、CN、NO2、C(O)R7、C(O)OR7又はS(O)27を表し、その他の記号は前記と同じ意味を表す。〕 Manufacturing method C
The compound shown by Formula (1E) can be manufactured by making the compound shown by Formula (1D), and an oxidizing agent react. The reaction is carried out according to the method described in Production Method B.
Figure 2019089711
[Wherein, Q 1 represents CN, NO 2 , C (O) R 7 , C (O) OR 7 or S (O) 2 R 7 , and the other symbols have the same meanings as described above. ]

製造法D
式(1D1)で示される化合物(以下、化合物(1D1)と記す。)は、化合物(1A)とシアナミドとを添加剤の存在下で反応させることにより製造することができる。

Figure 2019089711
〔式中、記号は前記と同じ意味を表す。〕
反応は、通常溶媒中で行われる。反応に用いられる溶媒としては、炭化水素類、エーテル類、ハロゲン化炭化水素類、アミド類、エステル類、スルホキシド類、ニトリル類、アルコール、水及びこれらの混合物等が挙げられる。
反応に用いられる添加剤としては、ヨードベンゼンジアセテート、ビス(トリフルオロアセトキシ)フェニルヨージド等が挙げられる。
反応には、化合物(1A)1モルに対して、通常シアナミドが1〜10モルの割合、添加剤が1〜10モルの割合で用いられる。
反応温度は通常−20〜150℃の範囲内である。反応時間は通常0.1〜120時間の範囲内である。
反応終了後は、反応混合物を水と混合した後、有機溶媒で抽出し、有機層を、乾燥、濃縮等の後処理操作に付すことにより化合物(1D1)を単離することができる。 Manufacturing method D
The compound represented by the formula (1D1) (hereinafter referred to as a compound (1D1)) can be produced by reacting the compound (1A) with cyanamide in the presence of an additive.
Figure 2019089711
Wherein the symbols have the same meanings as described above. ]
The reaction is usually carried out in a solvent. Examples of the solvent used for the reaction include hydrocarbons, ethers, halogenated hydrocarbons, amides, esters, sulfoxides, nitriles, alcohols, water, and mixtures thereof.
Examples of the additive used for the reaction include iodobenzene diacetate, bis (trifluoroacetoxy) phenyl iodide and the like.
In the reaction, 1 to 10 moles of cyanamide and 1 to 10 moles of the additive are generally used per 1 mole of the compound (1A).
The reaction temperature is usually in the range of -20 to 150 ° C. The reaction time is usually in the range of 0.1 to 120 hours.
After completion of the reaction, the reaction mixture is mixed with water and extracted with an organic solvent, and the organic layer is subjected to post-treatment operations such as drying and concentration to isolate compound (1D1).

製造法E
式(1F)で示される化合物(以下、化合物(1F)と記す。)は、化合物(1B)とアミノ化剤とを添加剤の存在下で反応させることにより製造することができる。

Figure 2019089711
〔式中、記号は前記と同じ意味を表す。〕
反応は、通常溶媒中で行われる。反応に用いられる溶媒としては、炭化水素類、エーテル類、ハロゲン化炭化水素類、アミド類、エステル類、ニトリル類、アルコール、水及びこれらの混合物等が挙げられる。
反応に用いられるアミノ化剤としては、アンモニア、ギ酸アンモニウム、カルバミン酸アンモニウム等が挙げられる。
添加剤としては、ヨードベンゼンジアセテート、ビス(トリフルオロアセトキシ)フェニルヨージド等が挙げられる。
反応には、化合物(1B)1モルに対して、通常アミノ化剤が1〜10モルの割合、添加剤が1〜10モルの割合で用いられる。
反応温度は通常−20〜150℃の範囲内である。反応時間は通常0.1〜120時間の範囲内である。
反応終了後は、反応混合物を濃縮等の後処理操作に付すことにより化合物(1F)を単離することができる。 Production method E
The compound represented by the formula (1F) (hereinafter referred to as the compound (1F)) can be produced by reacting the compound (1B) with an aminating agent in the presence of an additive.
Figure 2019089711
Wherein the symbols have the same meanings as described above. ]
The reaction is usually carried out in a solvent. Examples of the solvent used for the reaction include hydrocarbons, ethers, halogenated hydrocarbons, amides, esters, nitriles, alcohols, water and mixtures thereof.
Examples of the aminating agent used for the reaction include ammonia, ammonium formate, ammonium carbamate and the like.
Examples of the additive include iodobenzene diacetate, bis (trifluoroacetoxy) phenyl iodide and the like.
In the reaction, 1 to 10 moles of an aminating agent and 1 to 10 moles of an additive are generally used per 1 mole of a compound (1B).
The reaction temperature is usually in the range of -20 to 150 ° C. The reaction time is usually in the range of 0.1 to 120 hours.
After completion of the reaction, compound (1F) can be isolated by subjecting the reaction mixture to post-treatment procedures such as concentration.

製造法F
式(1G2)で示される化合物(以下、化合物(1G2)と記す。)は、式(1G1)で示される化合物(以下、化合物(1G1)と記す。)と式(M11)で示される化合物(以下、化合物(M11)と記す。)とを塩基の存在下で反応させることにより製造することができる。

Figure 2019089711
〔式中、X1は塩素原子、臭素原子、ヨウ素原子、メタンスルホニルオキシ基、トリフルオロメタンスルホニルオキシ基等の脱離基を表し、その他の記号は前記と同じ意味を表す。〕
反応は、通常溶媒中で行われる。反応に用いられる溶媒としては、炭化水素類、エーテル類、ハロゲン化炭化水素類、アミド類、エステル類、ニトリル類、アルコール、水及びこれらの混合物等が挙げられる。
反応に用いられる塩基としては例えば、有機塩基類、炭酸塩類、炭酸水素塩類、及び水素化ナトリウム、水素化カリウム、水素化リチウム等の水素化金属試薬(以下、水素化金属試薬類と記す。)が挙げられる。
反応には通常化合物(1G1)1モルに対して、化合物(M11)が1〜10モルの割合、塩基が1〜10モルの割合で用いられる。
反応温度は通常−20〜150℃の範囲内である。反応時間は通常0.1〜120時間の範囲内である。
反応終了後は、反応混合物を水と混合した後有機溶媒で抽出し、有機層を乾燥、濃縮する等の後処理操作を行うことにより化合物(1G2)を単離することができる。
化合物(M11)は、公知であるか、公知の方法に準じて製造することができる。 Manufacturing method F
The compound represented by the formula (1G2) (hereinafter referred to as a compound (1G2)) is a compound represented by the formula (1G1) (hereinafter referred to as a compound (1G1)) and the compound represented by the formula (M11) Hereinafter, it can be produced by reacting the compound (M11)) in the presence of a base.
Figure 2019089711
[Wherein, X 1 represents a leaving group such as chlorine atom, bromine atom, iodine atom, methanesulfonyloxy group, trifluoromethanesulfonyloxy group and the like, and the other symbols have the same meanings as described above. ]
The reaction is usually carried out in a solvent. Examples of the solvent used for the reaction include hydrocarbons, ethers, halogenated hydrocarbons, amides, esters, nitriles, alcohols, water and mixtures thereof.
As the base used for the reaction, for example, organic bases, carbonates, hydrogencarbonates and metal hydride reagents such as sodium hydride, potassium hydride and lithium hydride (hereinafter referred to as metal hydride reagents) Can be mentioned.
In the reaction, 1 to 10 moles of Compound (M11) and 1 to 10 moles of Base are usually used per 1 mole of Compound (1G1).
The reaction temperature is usually in the range of -20 to 150 ° C. The reaction time is usually in the range of 0.1 to 120 hours.
After completion of the reaction, the reaction mixture is mixed with water and then extracted with an organic solvent, and the organic layer is subjected to post-treatment operations such as drying and concentration to isolate the compound (1G2).
Compound (M11) is known or can be produced according to known methods.

製造法G
式(1A1)で示される化合物(以下、化合物(1A1)と記す。)は、式(A7)で示される化合物(以下、化合物(A7)と記す。)と式(M12)で示される化合物(以下、化合物(M12)と記す。)とをアゾ化合物存在下で反応させることにより製造することができる。

Figure 2019089711
〔式中、記号は前記と同じ意味を表す。〕
反応は、通常溶媒中で行われる。反応に用いられる溶媒としては、炭化水素類、エーテル類、ハロゲン化炭化水素類、エステル類及びこれらの混合物等が挙げられる。
反応に用いられるアゾ化合物としては、例えば、アゾジカルボン酸ジエチル、ビス(2−メトキシエチル)ジアゼン−1,2−ジカルボキシレートが挙げられる。
反応には通常化合物(A7)1モルに対して、化合物(M12)が1〜10モルの割合、アゾ化合物が1〜10モルの割合で用いられる。
反応温度は通常−20〜150℃の範囲内である。反応時間は通常0.1〜120時間の範囲内である。
反応終了後は、反応混合物を水と混合した後有機溶媒で抽出し、有機層を乾燥、濃縮する等の後処理操作を行うことにより化合物(1A1)を単離することができる。
化合物(A7)は、特開昭63−162680号公報に記載の方法に準じて製造することができる。 化合物(M12)は、公知であるか、公知の方法に準じて製造することができる。 Manufacturing method G
The compound represented by the formula (1A1) (hereinafter referred to as the compound (1A1)) is a compound represented by the formula (A7) (hereinafter referred to as the compound (A7)) and the compound represented by the formula (M12) Hereinafter, it can be produced by reacting the compound (M12)) in the presence of an azo compound.
Figure 2019089711
Wherein the symbols have the same meanings as described above. ]
The reaction is usually carried out in a solvent. Examples of the solvent used in the reaction include hydrocarbons, ethers, halogenated hydrocarbons, esters, and mixtures thereof.
Examples of the azo compound used for the reaction include diethyl azodicarboxylate and bis (2-methoxyethyl) diazene-1,2-dicarboxylate.
In the reaction, 1 to 10 moles of Compound (M12) and 1 to 10 moles of azo compound are usually used per 1 mole of Compound (A7).
The reaction temperature is usually in the range of -20 to 150 ° C. The reaction time is usually in the range of 0.1 to 120 hours.
After completion of the reaction, the reaction mixture is mixed with water and then extracted with an organic solvent, and the organic layer is subjected to post-treatment procedures such as drying and concentration to isolate the compound (1A1).
Compound (A7) can be produced according to the method described in JP-A-63-162680. Compound (M12) is known or can be produced according to known methods.

参考製造法A
化合物(A1)は、式(A2)で示される化合物(以下、化合物(A2)と記す。)とヒドロキシルアミンとを反応させることにより製造することができる。

Figure 2019089711
〔式中、記号は前記と同じ意味を表す。〕
反応は、例えば国際公開第2009/081891号に記載の方法に準じて実施される。 Reference manufacturing method A
The compound (A1) can be produced by reacting a compound represented by the formula (A2) (hereinafter referred to as a compound (A2)) with hydroxylamine.
Figure 2019089711
Wherein the symbols have the same meanings as described above. ]
The reaction is carried out, for example, according to the method described in WO 2009/081891.

参考製造法B
化合物(A2)は、式(A3)で示される化合物(以下、化合物(A3)と記す。)を酸化することにより製造することができる。

Figure 2019089711
〔式中、記号は前記と同じ意味を表す。〕
反応は製造法Bに記載の方法に準じて実施される。 Reference manufacturing method B
The compound (A2) can be produced by oxidizing a compound represented by the formula (A3) (hereinafter referred to as a compound (A3)).
Figure 2019089711
Wherein the symbols have the same meanings as described above. ]
The reaction is carried out according to the method described in Production Method B.

参考製造法C
式(A2−1)で示される化合物(以下、化合物(A2−1)と記す。)は、式(A4)で示される化合物(以下、化合物(A4)と記す。)と式(M1)で示される化合物(以下、化合物(M1)と記す。)とを反応させることにより製造することができる。

Figure 2019089711
〔式中、Y101はC1−C6アルキル基を表し、Mはカリウム、ナトリウム等のアルカリ金属を表し、その他の記号は前記と同じ意味を表す。〕
反応は、通常溶媒中で行われる。反応に用いられる溶媒としては、炭化水素類、エーテル類、ハロゲン化炭化水素類、アミド類、エステル類、ニトリル類、アルコール、水及びこれらの混合物等が挙げられる。
反応には、化合物(A4)1モルに対して、化合物(M1)が通常1〜10モルの割合で用いられる。
反応温度は通常−20〜150℃の範囲内である。反応時間は通常0.1〜120時間の範囲内である。
反応終了後は、反応混合物を抽出及び濃縮、等の後処理操作に付すことにより化合物(A2−1)を単離することができる。
化合物(A4)は、国際公開第2012/058134号に記載の方法に準じて製造することができる。 Reference manufacturing method C
The compound represented by Formula (A2-1) (hereinafter referred to as Compound (A2-1)) is a compound represented by Formula (A4) (hereinafter referred to as Compound (A4)) and Formula (M1). It can be produced by reacting the compound shown (hereinafter referred to as compound (M1)).
Figure 2019089711
[Wherein, Y 101 represents a C 1 -C 6 alkyl group, M represents an alkali metal such as potassium or sodium, and the other symbols have the same meanings as described above. ]
The reaction is usually carried out in a solvent. Examples of the solvent used for the reaction include hydrocarbons, ethers, halogenated hydrocarbons, amides, esters, nitriles, alcohols, water and mixtures thereof.
In the reaction, the compound (M1) is usually used in a proportion of 1 to 10 moles relative to 1 mole of the compound (A4).
The reaction temperature is usually in the range of -20 to 150 ° C. The reaction time is usually in the range of 0.1 to 120 hours.
After completion of the reaction, the compound (A2-1) can be isolated by subjecting the reaction mixture to post-treatment procedures such as extraction and concentration.
Compound (A4) can be produced according to the method described in WO 2012/058134.

参考製造法D
式(A2−2)で示される化合物(以下、化合物(A2−2)と記す。)は、式(A5)で示される化合物(以下、化合物(A5)と記す。)と式(M2)で示される化合物とを塩基の存在下で反応させることにより製造することができる。

Figure 2019089711
〔式中、記号は前記と同じ意味を表す。〕
反応は、国際公開第2015/004282号に記載の方法に準じて実施される。
化合物(A5)は、国際公開第2011/142356号に記載の方法に準じて製造することができる。
化合物(M2)は、公知であるか、公知の方法に準じて製造することができる。 Reference manufacturing method D
The compound represented by the formula (A2-2) (hereinafter referred to as the compound (A2-2)) is a compound represented by the formula (A5) (hereinafter referred to as the compound (A5)) and the compound represented by the formula (M2) It can be produced by reacting the compound shown in the presence of a base.
Figure 2019089711
Wherein the symbols have the same meanings as described above. ]
The reaction is carried out according to the method described in WO 2015/004282.
Compound (A5) can be produced according to the method described in WO 2011/142356.
Compound (M2) is known or can be produced according to known methods.

参考製造法E
式(A2−3)で示される化合物(以下、化合物(A2−3)と記す。)は、式(A6)で示される化合物(以下、化合物(A6)と記す。)と式(M3)で示される化合物とを塩基の存在下で反応させることにより製造することができる。

Figure 2019089711
〔式中、Y11はNR1112又はOR13を表し、その他の記号は前記と同じ意味を表す。〕
反応は国際公開第2013/008162号に記載の方法に準じて実施される。
化合物(A6)は、国際公開第2007/140317号に記載の方法に準じて製造することができる。
化合物(M3)は、公知であるか、公知の方法に準じて製造することができる。 Reference manufacturing method E
The compound represented by the formula (A2-3) (hereinafter referred to as the compound (A2-3)) is a compound represented by the formula (A6) (hereinafter referred to as the compound (A6)) and the formula (M3) It can be produced by reacting the compound shown in the presence of a base.
Figure 2019089711
[Wherein, Y 11 represents NR 11 R 12 or OR 13 and the other symbols have the same meanings as described above. ]
The reaction is carried out according to the method described in WO 2013/008162.
Compound (A6) can be produced according to the method described in WO2007 / 140317.
Compound (M3) is known or can be produced according to known methods.

参考製造法F
式(A3−1)で示される化合物(以下、化合物(A3−1)と記す。)は、式(A4)で示される化合物(以下、化合物(A4)と記す。)と式(M4)で示される化合物とを反応させることにより製造することができる。

Figure 2019089711
〔式中、記号は前記と同じ意味を表す。〕
反応はJournal of the Chemical Society, 1948,p.1501−1506に記載の方法に準じて製造することができる。
化合物(M4)は、公知であるか、公知の方法に準じて製造することができる。 Reference manufacturing method F
The compound represented by the formula (A3-1) (hereinafter referred to as the compound (A3-1)) is a compound represented by the formula (A4) (hereinafter referred to as the compound (A4)) and the compound represented by the formula (M4) It can be produced by reacting with a compound shown.
Figure 2019089711
Wherein the symbols have the same meanings as described above. ]
The reaction is described in Journal of the Chemical Society, 1948, p. It can manufacture according to the method as described in 1501-1506.
The compound (M4) is known or can be produced according to known methods.

参考製造法G
式(A3−2)で示される化合物(以下、化合物(A3−2)と記す。)は、式(A8)で示される化合物(以下、化合物(A8)と記す。)と式(M13)で示される化合物(以下、化合物(M13)と記す。)とを塩基の存在下で反応させることにより製造することができる。

Figure 2019089711
〔式中、記号は前記と同じ意味を表す。〕
反応は製造法Fの方法に準じて実施することができる。
化合物(A8)は、Bioorganic & Medicinal Chemistry Letters, 2016,26(3), p757−p760に記載の方法に準じて製造することができる。 Reference manufacturing method G
The compound represented by the formula (A3-2) (hereinafter referred to as the compound (A3-2)) is a compound represented by the formula (A8) (hereinafter referred to as the compound (A8)) and the compound represented by the formula (M13) It can be produced by reacting the compound shown below (hereinafter referred to as compound (M13)) in the presence of a base.
Figure 2019089711
Wherein the symbols have the same meanings as described above. ]
The reaction can be carried out according to the method of production method F.
Compound (A8) can be produced according to the method described in Bioorganic & Medicinal Chemistry Letters, 2016, 26 (3), p757-p760.

本発明防除剤は、通常、本発明化合物と、固体担体、液体担体、及び/又は界面活性剤等とを混合し、必要により固着剤、分散剤、安定剤等の製剤用補助剤を添加して、水和剤、顆粒水和剤、フロアブル剤、粒剤、ドライフロアブル剤、乳剤、水性液剤、油剤、くん煙剤、エアゾール剤、マイクロカプセル剤、毒餌剤、樹脂製剤、シャンプー剤、ペースト状製剤、泡沫剤、炭酸ガス製剤、錠剤等に製剤化して用いる。これらの製剤は蚊取り線香、電気蚊取りマット、液体蚊取り製剤、燻煙剤、燻蒸剤、シート製剤、スポットオン剤、経口処理剤に加工されて、使用されることもある。これらの製剤には本発明化合物が重量比で通常0.1〜99%、好ましくは0.2〜90%含有される。   The control agent of the present invention is usually prepared by mixing the compound of the present invention with a solid carrier, liquid carrier, and / or surfactant, and optionally adding formulation adjuvants such as fixing agents, dispersing agents, stabilizers and the like. Water dispersible granules, water dispersible granules, flowables, granules, dry flowables, emulsions, aqueous solutions, oils, smokes, aerosols, microcapsules, poison baits, resin formulations, shampoos, pastes It is formulated into a preparation, a foam, a carbon dioxide preparation, a tablet, etc. and used. These preparations may be used as processed into mosquito coil, electric mosquito mat, liquid mosquito formula, fuming agent, fumigant, sheet preparation, spot-on agent, oral treatment agent. These preparations contain the compound of the present invention in a weight ratio of usually 0.1 to 99%, preferably 0.2 to 90%.

固体担体としては、例えば、粘土類(例えば、カオリン、珪藻土、フバサミクレー、ベントナイト、酸性白土)、合成含水酸化珪素、タルク類、その他の無機鉱物(例えば、セリサイト、石英粉末、硫黄粉末、活性炭、炭酸カルシウム、)等の微粉末あるいは粒状物が挙げられる。
液体担体としては、例えば、水、アルコール類、ケトン類(例えば、アセトン、メチルエチルケトン、シクロヘキサノン)、芳香族炭化水素類(例えば、ベンゼン、トルエン、キシレン、エチルベンゼン、メチルナフタレン)、脂肪族炭化水素類(例えば、n−ヘキサン、灯油)、エステル類、ニトリル類、エーテル類、アミド類、ハロゲン化炭化水素類が挙げられる。
As a solid carrier, for example, clays (eg, kaolin, diatomaceous earth, fubasami clay, bentonite, acid clay), synthetic hydrous silicon oxide, talcs and other inorganic minerals (eg, sericite, quartz powder, sulfur powder, activated carbon, Fine powders or granules of calcium carbonate, etc. may be mentioned.
Examples of liquid carriers include water, alcohols, ketones (eg, acetone, methyl ethyl ketone, cyclohexanone), aromatic hydrocarbons (eg, benzene, toluene, xylene, ethylbenzene, methyl naphthalene), aliphatic hydrocarbons (eg, For example, n-hexane, kerosene), esters, nitriles, ethers, amides and halogenated hydrocarbons are mentioned.

界面活性剤としては、例えばアルキル硫酸エステル類、アルキルスルホン酸塩、アルキルアリールスルホン酸塩、アルキルアリールエーテル類及びそのポリオキシエチレン化物、ポリオキシエチレングリコールエーテル類、多価アルコールエステル類、糖アルコール誘導体が挙げられる。   As surfactants, for example, alkyl sulfates, alkyl sulfonates, alkyl aryl sulfonates, alkyl aryl ethers and their polyoxyethylene derivatives, polyoxyethylene glycol ethers, polyhydric alcohol esters, sugar alcohol derivatives Can be mentioned.

その他の製剤用補助剤としては、例えば固着剤、分散剤、安定剤があげられ、具体的にはカゼイン、ゼラチン、多糖類(例えば、デンプン、アラビヤガム、セルロース誘導体、アルギン酸)、リグニン誘導体、ベントナイト、糖類、合成水溶性高分子(例えば、ポリビニルアルコール、ポリビニルピロリドン、ポリアクリル酸類)、酸性りん酸イソプロピル、2,6−ジ−tert−ブチル−4−メチルフェノール、2−tert−ブチル−4−メトキシフェノールと3−tert−ブチル−4−メトキシフェノールとの混合物、植物油、鉱物油、脂肪酸又はそのエステル等が挙げられる。   Other pharmaceutical auxiliaries include, for example, fixing agents, dispersing agents and stabilizers, and specifically, casein, gelatin, polysaccharides (eg, starch, arabia gum, cellulose derivative, alginic acid), lignin derivative, bentonite, Saccharides, synthetic water-soluble polymers (eg, polyvinyl alcohol, polyvinyl pyrrolidone, polyacrylic acids), isopropyl acid phosphate, 2,6-di-tert-butyl-4-methylphenol, 2-tert-butyl-4-methoxy Mixtures of phenol and 3-tert-butyl-4-methoxyphenol, vegetable oils, mineral oils, fatty acids or esters thereof, and the like can be mentioned.

また、本発明化合物は、鉱物油、植物油等のオイル、又は界面活性剤等と混合して、有害生物の防除に用いてもよい。混合して用いることができるオイル、又は界面活性剤としてはNimbus(登録商標)、Assist(登録商標)、Aureo(登録商標)、Iharol(登録商標)、Silwet L−77(登録商標)、BreakThru(登録商標)、SundanceII(登録商標)、Induce(登録商標)、Penetrator(登録商標)、AgriDex(登録商標)、Lutensol A8(登録商標)、NP−7(登録商標)、Triton(登録商標)、Nufilm(登録商標)、Emulgator NP7(登録商標)、Emulad(登録商標)、TRITON X 45(登録商標)、AGRAL 90(登録商標)、AGROTIN(登録商標)、ARPON(登録商標)、EnSpray N(登録商標)、及びBANOLE(登録商標)等が挙げられる。 In addition, the compound of the present invention may be mixed with an oil such as a mineral oil or a vegetable oil, or with a surfactant or the like to be used for controlling pests. Oils that can be used as a mixture, or surfactants such as Nimbus (registered trademark), Assist (registered trademark), Aureo (registered trademark), Iharol (registered trademark), Silwet L-77 (registered trademark), BreakThru (Breakthrough) Sundance II (registered trademark), Sundance II (registered trademark), Induce (registered trademark), Penetrator (registered trademark), AgriDex (registered trademark), Lutensol A8 (registered trademark), NP-7 (registered trademark), Triton (registered trademark), Nufilm (Registered trademark), Emulgator NP7 (registered trademark), Emulad (registered trademark), TRITON X 45 (registered trademark), AGRAL 90 (registered trademark), AGROTIN (registered trademark), ARPON (registered trademark), EnSpray N (registered trademark) And BANOLE (registered trademark).

樹脂製剤の基材としては、例えば塩化ビニル系重合体、ポリウレタン等が挙げられる。これらの基材には必要によりフタル酸エステル類(フタル酸ジメチル、フタル酸ジオクチル等)、アジピン酸エステル類、ステアリン酸等の可塑剤を添加してもよい。樹脂製剤は該基材中に本発明化合物を通常の混練装置を用いて混練した後、射出成型、押出成型、プレス成型等により成型することにより得られ、必要により更に成型、裁断等の工程を経て、板状、フィルム状、テープ状、網状、ひも状等の樹脂製剤に加工される。これらの樹脂製剤は、例えば動物用首輪、動物用イヤータッグ、シート製剤、誘引ひも、園芸用支柱として加工される。
毒餌剤の基材としては、例えば穀物粉、植物油、糖、結晶セルロースが挙げられ、更に必要に応じて、ジブチルヒドロキシトルエン、ノルジヒドログアイアレチン酸等の酸化防止剤、デヒドロ酢酸等の保存料、トウガラシ末等の子供やペットによる誤食防止剤、チーズ香料、タマネギ香料、ピーナッツオイル等の害虫誘引性香料等が添加される。
As a base material of resin formulation, a vinyl chloride polymer, polyurethane, etc. are mentioned, for example. If necessary, plasticizers such as phthalic acid esters (such as dimethyl phthalate and dioctyl phthalate), adipic acid esters, and stearic acid may be added to these substrates. The resin preparation is obtained by kneading the compound of the present invention in the base using a conventional kneading apparatus and then molding it by injection molding, extrusion molding, press molding or the like, and if necessary, further processes such as molding and cutting Then, it is processed into a resin formulation such as plate, film, tape, net, cord and the like. These resin preparations are processed, for example, as animal collars, animal ear tags, sheet preparations, drawstrings, horticultural posts.
Examples of the base material of poison bait include cereal flour, vegetable oil, sugar, crystalline cellulose, and further, if necessary, antioxidant such as dibutyl hydroxytoluene, nordihydroguaiaretic acid, preservative such as dehydroacetic acid Also, an anti-mistake agent for children and pets such as capsicum powder, a cheese flavor, an onion flavor, a pest-inducing flavor such as peanut oil, etc. are added.

本発明防除剤の施用量は、気象条件、製剤形態、施用時期、施用方法、施用場所、対象病害、対象害虫、対象作物等によっても異なるが、本発明防除剤中の本発明化合物の量が、1000m2あたり、通常1〜500g、好ましくは2〜200gである。乳剤、水和剤、懸濁剤等は通常水で希釈して施用されるが、その場合の希釈後の本発明化合物の濃度は、通常0.0005〜2重量%、好ましくは0.005〜2重量%であり、粉剤、粒剤等は通常希釈することなくそのまま施用される Although the application amount of the control agent of the present invention varies depending on weather conditions, formulation form, application time, application method, application place, application disease, target disease, target pest, target crop, etc., the amount of the compound of the present invention in the control agent of the present invention is The amount is usually 1 to 500 g, preferably 2 to 200 g, per 1000 m 2 . Emulsions, wettable powders, suspensions and the like are usually diluted with water and then applied. The concentration of the compound of the present invention after dilution is usually 0.0005 to 2% by weight, preferably 0.005 to It is 2% by weight, and powders and granules are usually applied as they are without dilution.

本発明防除剤を施用する方法としては、本発明化合物が施用され得る形態であればその方法は特に限定されないが、例えば茎葉散布等の植物体への処理、土壌処理等の植物の栽培地への処理、種子消毒等の種子への処理、有害節足動物への処理等が挙げられる。また、シート状やひも状に加工した樹脂製剤を作物に巻き付ける、作物近傍に張り渡す、株元土壌に敷く等の方法により処理することもできる。
本発明防除剤を植物の茎葉に処理する場合又は植物を栽培する土壌に処理する場合は、本発明化合物は、土壌1000m2あたり、通常1〜500gである。種子に処理する場合は、種子1Kgに対して本発明防除剤中の本発明化合物の量が、通常0.001〜100g、好ましくは0.01〜50gの範囲で施用される。
乳剤、水和剤、フロアブル剤等は通常水で希釈して散布することにより処理する。この場合、本発明化合物の濃度は、通常0.0005〜2重量%である。粉剤、粒剤等は通常希釈することなくそのまま処理する。
The method of applying the control agent of the present invention is not particularly limited as long as the compound of the present invention can be applied, but, for example, treatment of plants such as foliage spraying, plant cultivation of soil treatment, etc. Treatment of seeds such as seed disinfection, treatment of harmful arthropods, and the like. In addition, the resin preparation processed into a sheet or string can be treated by a method such as wrapping around a crop, spreading it in the vicinity of a crop, spreading it on stock soil, or the like.
When the control agent of the present invention is treated on the stems and leaves of plants or in the soil where plants are grown, the amount of the compound of the present invention is usually 1 to 500 g per 1000 m 2 of soil. When the seed is treated, the amount of the compound of the present invention in the control agent of the present invention is generally applied in the range of 0.001 to 100 g, preferably 0.01 to 50 g based on 1 kg of the seed.
Emulsions, wettable powders, flowables and the like are usually treated by diluting with water and spraying. In this case, the concentration of the compound of the present invention is usually 0.0005 to 2% by weight. Powders, granules and the like are usually treated as such without dilution.

本発明防除剤を家屋内に生息する有害節足動物の防除に用いる場合、その施用量は、面上に処理する場合は処理面積1m2あたりの本発明化合物量で、通常、0.01〜1000mgであり、空間に処理する場合は処理空間1m3あたりの本発明化合物量で、通常、0.01〜500mgである。本発明防除剤が乳剤、水和剤、フロアブル剤等に製剤化されている場合は、通常、本発明化合物の濃度が0.1〜10000ppmとなるように水で希釈して施用し、油剤、エアゾール剤、燻煙剤、毒餌剤等はそのまま施用する。 When the control agent of the present invention is used for controlling harmful arthropods that live in a house, the application amount thereof is usually 0.01 to 10 parts by weight of the present compound per 1 m 2 of treated area when treated on a surface. The amount of the compound of the present invention per 1 m 3 of treatment space is usually 0.01 to 500 mg when treated in a space. When the control agent of the present invention is formulated into an emulsion, a wettable powder, a flowable, etc., it is usually diluted with water so that the concentration of the compound of the present invention becomes 0.1 to 10000 ppm, and applied. Aerosols, fuming agents, poison bait etc. are applied as they are.

本発明防除剤をウシ、ウマ、ブタ、ヒツジ、ヤギ、ニワトリ用の家畜、イヌ、ネコ、ラット、マウス等の小動物の外部寄生虫防除に用いる場合は、獣医学的に公知の方法が使用される。具体的な方法としては、全身抑制を目的にする場合には、例えば錠剤、飼料混入、坐薬、注射(筋肉内、皮下、静脈内、腹腔内等)により投与する方法が挙げられ、非全身的抑制を目的とする場合には、油剤もしくは水性液剤等を噴霧するポアオン処理もしくはスポットオン処理する方法、シャンプー製剤で動物を洗う方法又は樹脂製剤を首輪や耳札にして動物につける方法が挙げられる。家畜又は小動物の動物体に投与する場合の本発明化合物の量は、通常動物の体重1kgに対して、0.1〜1000mgの範囲である。   When the control agent of the present invention is used for ectoparasite control of small animals such as cattle, horses, pigs, sheep, goats, domestic animals for chickens, dogs, cats, rats, mice, etc., known veterinary methods are used. Ru. As a specific method, for the purpose of systemic suppression, for example, a method of administering by tablet, feed mixing, suppository, injection (intramuscular, subcutaneous, intravenous, intraperitoneal, etc.) can be mentioned, and non-systemic For the purpose of suppression, there may be mentioned a method of pour-on treatment or spot-on treatment of spraying oil solution or aqueous solution, a method of washing an animal with a shampoo preparation, or a method of attaching a resin preparation to an animal . The amount of the compound of the present invention when administered to domestic animals or small animals is usually in the range of 0.1 to 1000 mg per 1 kg of animal weight.

また、本発明防除剤は、畑、水田、芝生、果樹園等の農耕地における植物病害の防除剤として使用することができる。本発明化合物は、以下に挙げられる「植物」等を栽培する農耕地等において、当該農耕地の病害を防除することができる。また、本発明化合物は、当該農耕地の有害節足動物を防除することができる。   In addition, the control agent of the present invention can be used as a control agent for plant diseases in agricultural land such as fields, paddy fields, lawns, orchards. The compounds of the present invention can control diseases of the agricultural lands in agricultural lands and the like for cultivating the “plants” and the like listed below. In addition, the compound of the present invention can control harmful arthropods of the agricultural land.

農作物;トウモロコシ、イネ、コムギ、オオムギ、ライムギ、エンバク、ソルガム、ワタ、ダイズ、ピーナッツ、ソバ、テンサイ、ナタネ、ヒマワリ、サトウキビ、タバコ等、野菜;ナス科野菜(ナス、トマト、ピーマン、トウガラシ、ジャガイモ等)、ウリ科野菜(キュウリ、カボチャ、ズッキーニ、スイカ、メロン等)、アブラナ科野菜(ダイコン、カブ、セイヨウワサビ、コ−ルラビ、ハクサイ、キャベツ、カラシナ、ブロッコリー、カリフラワー等)、キク科野菜(ゴボウ、シュンギク、アーティチョーク、レタス等)、ユリ科野菜(ネギ、タマネギ、ニンニク、アスパラガス)、セリ科野菜(ニンジン、パセリ、セロリ、アメリカボウフウ等)、アカザ科野菜(ホウレンソウ、フダンソウ等)、シソ科野菜(シソ、ミント、バジル等)、イチゴ、サツマイモ、ヤマノイモ、サトイモ等、花卉、観葉植物、
果樹;仁果類(リンゴ、セイヨウナシ、ニホンナシ、カリン、マルメロ等)、核果類(モモ、スモモ、ネクタリン、ウメ、オウトウ、アンズ、プルーン等)、カンキツ類(ウンシュウミカン、オレンジ、レモン、ライム、グレープフルーツ等)、堅果類(クリ、クルミ、ハシバミ、アーモンド、ピスタチオ、カシューナッツ、マカダミアナッツ等)、液果類(ブルーベリー、クランベリー、ブラックベリー、ラズベリー等)、ブドウ、カキ、オリーブ、ビワ、バナナ、コーヒー、ナツメヤシ、ココヤシ等、
果樹以外の樹;チャ、クワ、花木、街路樹(トネリコ、カバノキ、ハナミズキ、ユーカリ、イチョウ、ライラック、カエデ、カシ、ポプラ、ハナズオウ、フウ、プラタナス、ケヤキ、クロベ、モミノキ、ツガ、ネズ、マツ、トウヒ、イチイ)等。
Agricultural crops; corn, rice, wheat, barley, rye, oats, sorghum, cotton, soybeans, peanuts, buckwheat, sugar beet, rape, sunflower, sugar cane, tobacco etc. vegetables; solanaceous vegetables (eggplant, tomato, pepper, pepper, potato Etc.), Cucurbitaceae vegetables (cucumber, pumpkin, zucchini, watermelon, melon etc.), Brassicaceae vegetables (Japanese radish, turnip, horseradish, horse mackerel, Chinese cabbage, cabbage, mustard, broccoli, cauliflower etc.) Burdock, sage, artichoke, lettuce, etc., liliaceous vegetables (green onion, onion, garlic, asparagus), pelvic vegetables (carrots, parsley, celery, American buffalo, etc.), lizardaceous vegetables (spinach, swiss etc), perilla Department of vegetables (sesame, mint, basil ), Strawberry, sweet potato, yam, taro, etc., flowers, foliage plants,
Fruits; Fruits (apples, pears, Japanese pears, cullins, quince etc.), Core fruits (momo, plums, nectarines, jujubes, apricots, prunes etc.), citrus fruits (palms, oranges, lemons, limes, grapefruits) Etc), nuts (nuts, walnuts, hazelnuts, almonds, pistachios, cashews, macadamias etc), berries (blueberries, cranberries, blackberries, raspberries etc), grapes, oysters, olives, loquats, bananas, coffee, etc. Date palm, coconut palm, etc.
Trees other than fruit trees; tea, mulberry, flowering trees, street trees (astera, birch, dogwood, eucalyptus, eucalyptus, ginkgo, lilac, maple, oak, poplar, persimmon, perennial, fusarium, plananas, persimmon, perianthus, birch, fir tree, tsuga, nezu, pine Spruce, yew) etc.

上記植物には遺伝子組換え作物も含まれる。   The above plants also include genetically modified crops.

本発明化合物により防除することができる有害生物としては、例えば糸状菌等の植物病原菌、及び有害節足動物が挙げられ、より詳しくは以下が挙げられるが、これらに限定されるものではない。   Examples of pests that can be controlled by the compound of the present invention include, for example, plant pathogens such as filamentous fungi and harmful arthropods. More specifically, the following may be mentioned, but the present invention is not limited thereto.

植物病原菌としては、以下が挙げられる。
イネのいもち病(Magnaporthe grisea)、ごま葉枯病(Cochliobolus miyabeanus)、紋枯病(Rhizoctonia solani)、馬鹿苗病(Gibberella fujikuroi)、黄化萎縮病(Sclerophthora macrospora);コムギのうどんこ病(Erysiphe graminis)、赤かび病(Fusarium graminearum、F. avenaceum、F. culmorum、Microdochium nivale)、さび病(Puccinia striiformis、P. graminis、P. recondita)、紅色雪腐病(Micronectriella nivale, M.majus)、雪腐小粒菌核病(Typhula sp.)、裸黒穂病(Ustilago tritici)、なまぐさ黒穂病(Tilletia caries、T.controversa)、眼紋病(Pseudocercosporella herpotrichoides)、葉枯病(Septoria tritici)、ふ枯病(Stagonospora nodorum)、黄斑病(Pyrenophora tritici-repentis)、リゾクトニア属菌による苗立枯れ病(Rhizoctonia solani)、立枯病(Gaeumannomyces graminis);オオムギのうどんこ病(Erysiphe graminis)、赤かび病(Fusarium graminearum、F. avenaceum、F. culmorum、Microdochium nivale)、さび病(Puccinia striiformis、P.graminis、P.hordei)、裸黒穂病(Ustilago nuda)、雲形病(Rhynchosporium secalis)、網斑病(Pyrenophora teres)、斑点病(Cochliobolus sativus)、斑葉病(Pyrenophora graminea)、ラムラリア病(Ramularia collo−cygni)、リゾクトニア属菌による苗立枯れ病(Rhizoctonia solani);トウモロコシのさび病(Puccinia sorghi)、南方さび病(Puccinia polysora)、すす紋病(Setosphaeria turcica)、熱帯性さび病(Physopella zeae)、ごま葉枯病(Cochliobolus heterostrophus)、炭そ病(Colletotrichum graminicola)、グレーリーフスポット病(Cercospora zeae−maydis)、褐斑病(Kabatiella zeae)、ファエオスファエリアリーフスポット病(Phaeosphaeria maydis)ディプローディア病(Stenocarpella maydis、Stenocarpella macrospora)、ストークロット病(Fusarium graminearum、Fusarium verticilioides、Colletotrichum graminicola)、黒穂病(Ustilago maydis);ワタの炭そ病(Colletotrichum gossypii)、白かび病(Ramuraria areola)、黒斑病(Alternaria macrospora、A.gossypii)、Thielaviopsis属菌によるBlack root rot病 (Thielaviopsis basicola);コーヒーのさび病(Hemileia vastatrix)、リーフスポット病(Cercospora coffeicola);ナタネの菌核病(Sclerotinia sclerotiorum)、黒斑病(Alternaria brassicae)、根朽病(Phoma lingam);サトウキビのさび病 (Puccinia melanocephela、Puccinia kuehnii)、黒穂病 (Ustilago scitaminea);ヒマワリのさび病 (Puccinia helianthi)、べと病(Plasmopara halstedii);カンキツ類の黒点病(Diaporthe citri)、そうか病(Elsinoe fawcetti)、果実腐敗病(Penicillium digitatum、P. italicum)、疫病 (Phytophthora parasitica、Phytophthora citrophthora);リンゴのモニリア病(Monilinia mali)、腐らん病(Valsa ceratosperma)、うどんこ病(Podosphaera leucotricha)、斑点落葉病(Alternaria alternata apple pathotype)、黒星病(Venturia inaequalis)、炭そ病(Glomerella cingulata)、褐斑病(Diplocarpon mali)、輪紋病(Botryosphaeria berengeriana)、疫病 (Phytophtora cactorum);ナシの黒星病(Venturia nashicola、V. pirina)、黒斑病(Alternaria alternata Japanese pear pathotype)、赤星病(Gymnosporangium haraeanum);モモの灰星病(Monilinia fructicola)、黒星病(Cladosporium carpophilum)、フォモプシス腐敗病(Phomopsis sp.);ブドウの黒とう病(Elsinoe ampelina)、晩腐病(Glomerella cingulata)、うどんこ病(Uncinula necator)、さび病(Phakopsora ampelopsidis)、ブラックロット病(Guignardia bidwellii)、べと病(Plasmopara viticola);カキの炭そ病(Gloeosporium kaki)、落葉病(Cercospora kaki、Mycosphaerella nawae);ウリ類の炭そ病(Colletotrichum lagenarium)、うどんこ病(Sphaerotheca fuliginea)、つる枯病(Didymella bryoniae)、褐斑病(Corynespora cassiicola)、つる割病(Fusarium oxysporum)、べと病(Pseudoperonospora cubensis)、疫病(Phytophthora sp.)、苗立枯病(Pythium sp.);トマトの輪紋病(Alternaria solani)、葉かび病(Cladosporium fulvum)、すすかび病(Pseudocercospora fuligena)、疫病(Phytophthora infestans)、うどんこ病(Leveillula taurica);ナスの褐紋病(Phomopsis vexans)、うどんこ病(Erysiphe cichoracearum);アブラナ科野菜の黒斑病(Alternaria japonica)、白斑病(Cercosporella brassicae)、根こぶ病(Plasmodiophora brassicae)、べと病(Peronospora parasitica);ネギのさび病(Puccinia allii);ダイズの紫斑病(Cercospora kikuchii)、黒とう病(Elsinoe glycines)、黒点病(Diaporthe phaseolorum var. sojae)、さび病(Phakopsora pachyrhizi)、褐色輪紋病(Corynespora cassiicola)、炭疽病(Colletotrithum glycines、C.truncatum)、葉腐病(Rhizoctonia solani)、褐紋病(Septoria glycines)、斑点病(Cercospora sojina)、菌核病(Sclerotinia sclerotiorum)、うどんこ病(Microspaera diffusa)、茎疫病 (Phytophthora sojae)、べと病(Peronospora manshurica)、突然死病(Fusarium virguliforme);インゲンの菌核病(Sclerotinia sclerotiorum)、さび病(Uromyces appendiculatus)、角斑病(Phaeoisariopsis griseola)、炭そ病(Colletotrichum lindemuthianum);ラッカセイの黒渋病(Cercospora personata)、褐斑病(Cercospora arachidicola)、白絹病(Sclerotium rolfsii);エンドウのうどんこ病(Erysiphe pisi);ジャガイモの夏疫病(Alternaria solani)、疫病(Phytophthora infestans)、緋色腐敗病 (Phytophthora erythroseptica)、粉状そうか病 (Spongospora subterranea f. sp. subterranea)、半身萎凋病(Verticillium albo−atrum、V. dahliae、V. nigrescens);イチゴのうどんこ病(Sphaerotheca humuli);チャの網もち病(Exobasidium reticulatum)、白星病(Elsinoe leucospila)、輪斑病(Pestalotiopsis sp.)、炭そ病(Colletotrichum theae−sinensis);タバコの赤星病(Alternaria longipes)、炭そ病(Colletotrichum tabacum)、べと病(Peronospora tabacina)、疫病(Phytophthora nicotianae);テンサイの褐斑病(Cercospora beticola)、葉腐病(Thanatephorus cucumeris)、根腐病(Thanatephorus cucumeris)、黒根病(Aphanomyces cochlioides);バラの黒星病(Diplocarpon rosae)、うどんこ病(Sphaerotheca pannosa);キクの褐斑病(Septoria chrysanthemi−indici)、白さび病(Puccinia horiana);タマネギの白斑葉枯病(Botrytis cinerea、B. byssoidea、B. squamosa)、灰色腐敗病(Botrytis alli)、小菌核性腐敗病(Botrytis squamosa);種々の作物の灰色かび病(Botrytis cinerea)、菌核病(Sclerotinia sclerotiorum);ダイコン黒斑病(Alternaria brassicicola);シバのダラースポット病(Sclerotinia homoeocarpa)、シバのブラウンパッチ病及びラージパッチ病(Rhizoctonia solani);並びにバナナのシガトカ病(Mycosphaerella fijiensis、Mycosphaerella musicola)。
Aspergillus属、Penicillium属、Fusarium属、Gibberella属、Tricoderma属、Thielaviopsis属、Rhizopus属、Mucor属、Corticium属、Phoma属、Rhizoctonia属、及びDiplodia属菌等によって引き起こされる、各種作物の種子病害又は生育初期の病害。Polymyxa属又はOlpidium属等によって媒介される各種作物のウイルス病。
イネの苗立枯細菌病(Burkholderia plantarii);キュウリの斑点細菌病(Pseudomonas syringae pv. Lachrymans);ナスの青枯病(Ralstonia solanacearum)、カンキツのかいよう病(Xanthomonas citri);ハクサイの軟腐病(Erwinia carotovora)等。
The plant pathogens include the following.
Rice blast fungus (Magnaporthe grisea), sesame leaf blight (Cochliobolus miyabeanus), sheath blight (Rhizoctonia solani), fool disease (Gibberella fujikuroi), yellow dwarf (Sclerophthora macrospora); wheat powdery mildew (Erysiphe) of wheat graminis), Fusarium head blight (Fusarium graminearum, F. avenaceum, F. culmorum, Microdochium nivale), rust (Puccinia striiformis, P. graminis, P. recondita), scarlet snow rot (Micronectriella nivale, M. majus), Small rot of snowflake (Typhula sp.), Bare broom scrotum (Ustilago tritici), lumber scab (Tilletia caries, T. controversa), eye blight (Pseudocercosporella herpotrichoides), leaf blight (Septoria tritici), blight Disease (Stagonospora nodorum), yellow spot (Pyrenophora tritici-repentis), rhizoctonia spp. Seedling blight (Rhizoctonia solani), blight (Gaeumannomyces graminis); barley powdery mildew (Erysiphe graminis), mildew Fusarium gramine arum, F. avenaceum, F. culmorum, Microdochium nivale), rust (Puccinia striiformis, P. graminis, P. hordei), naked panicle (Ustilago nuda), cloud disease (Rhynchosporium secalis), web spot (Pyrenophora teres) Blight disease (Cochliobolus sativus), leaf blight (Pyrenophora graminea), ramularia disease (Ramularia collo-cygni), seedling blight of rhizoctonia (Rhizoctonia solani); rust of maize (Puccinia sorghi), southern rust Disease (Puccinia polysora), soot disease (Setosphaeria turcica), tropical rust (Physopella zeae), sesame leaf blight (Cochliobolus heterostrophus), anthracnose (Colletotrichum graminicola), gray leaf spot disease (Cercospora zeae-maydis) , Brown spot (Kabatiella zeae), Phaeospha area leaf spot (Phaeosphaeria maydis) diplodia (Stenocarpella maydis, Stenocarpella macrospora), Stochlot's disease (Fusar) ium graminearum, Fusarium verticilioides, Colletotrichum graminicola), black scab (Ustilago maydis); cotton anthracnose (Colletotrichum gossypii), scab (Ramuraria areola), black scab (Alternaria macrospora, A. gossypii), genus Thieliviosis Black root rot disease (Thielaviopsis basicola); coffee rust (Hemileia vastatrix), leaf spot disease (Cercospora coffeicola); rapeseed sclerotia sclerotia (Sclerotinia sclerotiorum), black spot (Alternaria brassicae), root rot (Phoma) lingam); sugar cane rust (Puccinia melanocephala, Puccinia kuehnii), panicle sickness (Ustilago scitaminea); sunflower rust (Puccinia helianthi), downy mildew (Plasmopara halstedii); citrus sweet spot (Diaporthe citri) Disease (Elsinoe fawcetti), fruit rot (Penicillium digitatum, P. italicum), plague (Phytophthora parasitica, Phytophthora citrophthora); apple monilia (Monilinia) mali), rot fungus (Valsa ceratosperma), powdery mildew (Podosphaera leucotricha), spotted leaf rot (Alternaria alternata apple pathotype), scab (Venturia inaequalis), anthracnose (Glomerella cingulata), brown spot (Diplocapon mali) , Botryosmia (Botryosphaeria berengeriana), Plague (Phytophtora cactorum); Scab of the pear (Venturia nashicola, V. pirina), black spot (Alternaria alternata Japanese pear pathotype), red star disease (Gymnosporangium haraeanum); Disease (Monilinia fructicola), scab (Cladosporium carpophilum), Phomopsis rot (Phomopsis sp.); Grape scab (Elsinoe ampelina), late rot (Glomerella cingulata), powdery mildew (Uncinula necator), rust (Phakopsora ampelopsidis), black-lot disease (Guignardia bidwellii), downy mildew (Plasmoparaviticola); anthracnose of oyster (Gloeosporium kaki), leaf disease (Cercospora kaki, Mycosphaerella nawae) Burial anthracnose (Colletotrichum lagenarium), powdery mildew (Sphaerotheca fuliginea), spine blight (Didymella bryoniae), brown spot (Corynespora cassiicola), scab (Fusarium oxysporum), downy mildew (Pseudoperonospora cubensis) , Plague (Phytophthora sp.), Seedling blight (Pythium sp.); Tomato blight (Alternaria solani), leaf blight (Cladosporium fulvum), leaf blight (Pseudocercospora fuligena), plague (Phytophthora infestans), Powdery mildew (Leveillula taurica); eggplant (Phomopsis vexans), powdery mildew (Erysiphe cichoracearum); Brassica cruciferum (Alternaria japonica), white spot (Cercosporella brassicae), clubbing disease (Plasmodiophora) brassicae), downy mildew (Peronospora parasitica); green onion (Puccinia allii); soybean purpura (Cercospora kikuchii), black scab (Elsinoe glycines), black spot disease (Diaporthe phaseolorum var. sojae), Disease (Phakopsora pachyrhizi), brown ring disease (Corynespora cassiicola), anthracnose (Colletotrithum glycines, C. truncatum), leaf blight (Rhizoctonia solani), brown disease (Septoria glycines), spot disease (Cercospora sojina) Nuclear disease (Sclerotinia sclerotiorum), powdery mildew (Microspaera diffusa), stem blight (Phytophthora sojae), downy mildew (Peronospora manshurica), sudden death (Fusarium virguliforme); sclerotiosis of green beans (Sclerotinia sclerotiorum) (Uromyces appendiculatus), Angular mildew (Phaeoisariopsis griseola), Anthracnose (Colletotrichum lindemuthianum); Peanut (Cercospora personata), Brown spot (Cercospora arachidicola), White scab (Sclerotium rolfsii); Blight (Erysiphe pisi); potato blight (Alternaria solani), blight (Phytophthora infestans), green rot (Phytophthora erythropeptica), powdery mildew (Spongospora subterranea f. sp. subterranea), half body wilt (Verticillium albo-atrum, V. dahliae, V. nigrescens); powdery mildew of strawberries (Sphaerotheca humuli); tea scab (Exobasidium reticulatum), scab (Elsinoe leucospila), Rot blotch (Pestalotiopsis sp.), Anthracnose (Colletotrichum theae-sinensis); Tobacco scab (Alternaria longipes), Anthracnose (Colletotrichum tabacum), Downy mildew (Peronospora tabacina), Downy mildew (Phytophthora nicotianae); Sugar beet brown spot (Cercospora beticola), leaf blight (Thanatephorus cucumeris), root rot (Thanatephorus cucumeris), black root disease (Aphanomyces cochlioides); Brown spot of chrysanthemum (Septoria chrysanthemi-indici), white rust (Puccinia horiana); Botrytis of onion (Botrytis cinerea, B. byssoidea, B. squamosa), gray rot (Botrytis alli), small fungus nucleus Sexual rot (Botryt is squamosa); Botrytis cinerea, Sclerotinia sclerotiorum of various crops; Radish radish (Alternaria brassicicola); Dollar spot disease of Shiba (Sclerotinia homoeocarpa), Brown patch disease of Shiva and large Patch disease (Rhizoctonia solani); and Sigatoka disease of bananas (Mycosphaerella fijiensis, Mycosphaerella musicola).
Seed disease or early growth of various crops caused by Aspergillus spp., Penicillium sp., Fusarium sp., Gibberella sp., Tricoderma sp., Thieloviopsis sp., Rhizopus sp., Rhizopus sp., Mucor sp., Corcium sp., Phoma, Rhizoctonia sp., Diplodia sp. Diseases of Virus diseases of various crops that are mediated by Polymyxa or Olpidium etc.
Seedling bacterial blight of rice (Burkholderia plantarii); spotted blight of cucumber (Pseudomonas syringae pv. Lachrymans); blight of eggplant (Ralstonia solanacearum), citrus blight of citrus (Xanthomonas citri); soft rot of Chinese cabbage (Erwinia) carotovora) etc.

有害節足動物としては、以下が挙げられる。
半翅目害虫(Hemiptera):ヒメトビウンカ(Laodelphax striatellus)、トビイロウンカ(Nilaparvata lugens)、セジロウンカ(Sogatella furcifera)、トウモロコシウンカ(Peregrinus maidis)、キタウンカ(Javesella pellucida)、クロフツノウンカ(Perkinsiella saccharicida)、Tagosodes orizicolus等のウンカ科(Delphacidae);ツマグロヨコバイ(Nephotettix cincticeps)、タイワンツマグロヨコバイ(Nephotettix virescens)、クロスジツマグロヨコバイ(Nephotettix nigropictus)、イナズマヨコバイ(Recilia dorsalis)、チャノミドリヒメヨコバイ(Empoasca onukii)、ジャガイモヒメヨコバイ(Empoasca fabae)、コーンリーフホッパー(Dalbulus maidis)、シロオオヨコバイ(Cofana spectra)等のヨコバイ科(Cicadellidae);Mahanarva posticata、Mahanarva fimbriolata等のコガシラアワフキムシ科(Cercopidae);マメクロアブラムシ(Aphis fabae)、ダイズアブラムシ(Aphis glycines)、ワタアブラムシ(Aphis gossypii)、ヨーロッパリンゴアブラムシ(Aphis pomi)、ユキヤナギアブラムシ(Aphis spiraecola)、モモアカアブラムシ(Myzus persicae)、ムギワラギクオマルアブラムシ(Brachycaudus helichrysi)、ダイコンアブラムシ(Brevicoryne brassicae)、Rosy apple aphid(Dysaphis plantaginea)、ニセダイコンアブラムシ(Lipaphis erysimi)、チューリップヒゲナガアブラムシ(Macrosiphum euphorbiae)、ジャガイモヒゲナガアブラムシ(Aulacorthum solani)、レタスヒゲナガアブラムシ(Nasonovia ribisnigri)、ムギクビレアブラムシ(Rhopalosiphum padi)、トウモロコシアブラムシ(Rhopalosiphum maidis)、ミカンクロアブラムシ(Toxoptera citricidus)、モモコフキアブラムシ(Hyalopterus pruni)、ヒエノアブラムシ(Melanaphis sacchari)、オカボノクロアブラムシ(Tetraneura nigriabdominalis)、カンシャワタアブラムシ(Ceratovacuna lanigera)、リンゴワタムシ(Eriosoma lanigerum)等のアブラムシ科(Aphididae);ブドウネアブラムシ(Daktulosphaira vitifoliae)、Pecan phylloxera(Phylloxera devastatrix)、Pecan leaf phylloxera(Phylloxera notabilis)、Southern pecan leaf phylloxera(Phylloxera russellae)等のネアブラムシ科(Phylloxeridae);ツガカサアブラムシ(Adelges tsugae)、Adelges piceae、ヒメカサアブラムシ(Aphrastasia pectinatae)等のカサアブラムシ科(Adelgidae);イネクロカメムシ(Scotinophara lurida)、Malayan rice black bug(Scotinophara coarctata)、アオクサカメムシ(Nezara antennata)、トゲシラホシカメムシ(Eysarcoris aeneus)、オオトゲシラホシカメムシ(Eysarcoris lewisi)、シラホシカメムシ(Eysarcoris ventralis)、ムラサキシラホシカメムシ(Eysarcoris annamita)、クサギカメムシ(Halyomorpha halys)、ミナミアオカメムシ(Nezara viridula)、Brown stink bug(Euschistus heros)、Red banded stink bug(Piezodorus guildinii)、Oebalus pugnax、Dichelops melacanthus等のカメムシ科(Pentatomidae);Burrower brown bug(Scaptocoris castanea)等のツチカメムシ科(Cydnidae);ホソヘリカメムシ(Riptortus pedestris)、クモヘリカメムシ(Leptocorisa chinensis)、ホソクモヘリカメムシ(Leptocorisa acuta)等のホソヘリカメムシ科(Alydidae);ホソハリカメムシ(Cletus punctiger)、アシビロヘリカメムシ(Leptoglossus australis)等のヘリカメムシ科(Coreidae);カンシャコバネナガカメムシ(Caverelius saccharivorus)、コバネヒョウタンナガカメムシ(Togo hemipterus)、アメリカコバネナガカメムシ(Blissus leucopterus)等のナガカメムシ科(Lygaeidae);アカヒゲホソミドリカスミカメ(Trigonotylus caelestialium)、アカスジカスミカメ(Stenotus rubrovittatus)、フタトゲムギカスミカメ(Stenodema calcarata)、サビイロカスミカメ(Lygus lineolaris)等のカスミカメムシ科(Miridae);オンシツコナジラミ(Trialeurodes vaporariorum)、タバココナジラミ(Bemisia tabaci)、ミカンコナジラミ(Dialeurodes citri)、ミカントゲコナジラミ(Aleurocanthus spiniferus)、チャトゲコナジラミ(Aleurocanthus camelliae)、ヒサカキワタフキコナジラミ(Pealius euryae)等のコナジラミ科(Aleyrodidae);シュロマルカイガラムシ(Abgrallaspis cyanophylli)、アカマルカイガラムシ(Aonidiella aurantii)、ナシマルカイガラムシ(Diaspidiotus perniciosus)、クワシロカイガラムシ(Pseudaulacaspis pentagona)、ヤノネカイガラムシ(Unaspis yanonensis)、ニセヤノネカイガラムシ(Unaspis citri)、等のマルカイガラムシ科(Diaspididae);ルビーロウムシ(Ceroplastes rubens)等のカタカイガラムシ科(Coccidae);イセリアカイガラムシ(Icerya purchasi)、キイロワタフキカイガラムシ(Icerya seychellarum)等のワタフキカイガラムシ科(Margarodidae);ナスコナガイガラムシ(Phenacoccus solani)、クロテンコナカイガラムシ(Phenacoccus solenopsis)、フジコナカイガラムシ(Planococcus kraunhiae)、クワコナカイガラムシ(Pseudococcus comstocki)、ミカンコナカイガラムシ(Planococcus citri)、ガハニコナカイガラムシ(Pseudococcus calceolariae)、ナガオコナカイガラムシ(Pseudococcus longispinus)、タトルミーリーバグ(Brevennia rehi)等のコナカイガラムシ科(Pseudococcidae);ミカンキジラミ(Diaphorina citri)、ミカントガリキジラミ(Trioza erytreae)、ナシキジラミ(Cacopsylla pyrisuga)、チュウゴクナシキジラミ(Cacopsylla chinensis)、ジャガイモトガリキジラミ(Bactericera cockerelli)、Pear psylla(Cacopsylla pyricola)等のキジラミ科(Psyllidae);プラタナスグンバイ(Corythucha ciliata)、アワダチソウグンバイ(Corythucha marmorata)、ナシグンバイ(Stephanitis nashi)、ツツジグンバイ(Stephanitis pyrioides)等のグンバイムシ科(Tingidae);トコジラミ(Cimex lectularius)等のトコジラミ科(Cimicidae)及びGiant Cicada(Quesada gigas)等のセミ科(Cicadidae)。
The harmful arthropods include the following.
Semi-lepidoptera (Hemiptera): Hemetobiunka (Laodelphax striatellus), Tobiirounka (Nilaparvata lugens), Sejirounka (Sogatella furcifera), Cornflower (Peregrinus maidis), Lobluntia (Javesella pellucida), Black-tailed Ubiclusi Leafhopper family (Delphacidae); green leafhopper (Nephotettix cincticeps), giant leafhopper green leafhopper (Nephotettix virescens), black leafhopper green leafhopper (Nephotettix nigropictus), green leafhopper leafworm (Recilia dorsalis), green leafhopper foliage ), Corn leaf hopper (Dalbulus maidis), white leafhopper (Cofana spectra), etc., leafhopper family (Cicadelidae); Mahanarva posticata, Mahanarva fimbriolata, etc. (Cercopidae); Brash beetle (Aphis fabae), soybean aphid (Aphis glycines), cotton aphid (Aphis gossypii), European apple aphid (Aphis pomi), black-and-white aphid (Aphis spiraecola), green-billed aphid (Myzus persicae), blue-toothed aphid , Radish aphids (brevicoryne brassicae), Rosy apple aphid (Dysaphis plantaginea), imago radish aphids (Lipaphis erysimi), tulip pokeweed aphids (Macrosiphum euphorbiae), potato pokeweed aphids (Macrosiphum euphorbiae), potato pokeweed aphid (Alacorth cichalis). Aphids (Rhopalosiphum padi), corn aphids (Rhopalosiphum maidis), red-handed aphids (Toxoptera citricidus), Peach coptis Aphid (Hyalopterus pruni), bryophytes (Melanaph) Aphididae (Aphididae), such as the black-tailed aphid (Tetranaura nigriabdominalis), the yellow-billed aphid (Ceratovacuna lanigera), and the like (Eriosoma lanigerum); Leaf phylloxera (Phylloxera notabilis), Southern pecan leaf phylloxera (Phylloxera russellae) and other nematode (Phylloxeridae); A rice black bug (Scotinophara lurida), a Malayan rice black bug (Scotinophara coarctata), a green bug (Nezara antennata), a goby bug (Eysarcoris aeneus), a goby bug (Eysarcoris lewisi), a goby beetle (Eysarcoris lewisi), village Blue-headed stink bug (Eysarcoris annamita), Gray-backed bug (Halyomorpha halys), South African stink bug (Nezara viridula), Brown stink bug (Euschistus heros), Red banded stink bug (Piezodorus guildinii), Oebalus pugnax, etc. Brentaridae (Cydnidae), such as Burrower brown bug (Scaptocoris castanea); ;; Helicidae (Coreidae), such as Cletus punctiger, Leptoglossus australis, etc .; Caverelius saccharivorus, Togo hemipterus, Bugs such as Blissus leucopterus) (Lygaeidae); Trichonotidae, such as Trigonotylus caelestialium, Red-handed Tortoise (Stenotus rubrovittatus), Green-winged Tufted Turtle (Stenodema calcarata), Lys-biosis (Lygus linealis) etc. , Bemisia tabaci (Bemisia tabaci), Orange leafworm (Dialeurodes citri), Red-winged leafhopper (Aleurocanthus spiniferus), White-tailed lice (Aleurocanthus camelliae), White-leafed leafworm (Pealius euryae), etc. (Abgrallaspis cyanophylli), Red-backed scale insect (Aonidiella aurantii), Yellow-backed scale insect (Diaspidiotus perniciosus), Red-tailed scale insect (Pseudaulacaspis pentagona), Red-winged scale insect (Unaspis yanonensis), Red-tailed mealybug (Unaspis citri), etc., Marukabidae (Diaspididae); ruby (Ceroplastes rubens), etc., cataclyssidae (Coccidae); Plasmodidae (Margarodidae); Plasmodium (Phenacoccus solani), Plasmodium (Phenacoccus sorenopsis), Plasmodium (Planococcus kraunhiae), Crucifer (Pseudococcus comstocki), Plasmodium (Porococcus) (Pseudococcus calceolariae), mealybug (Pseudococcus longispinus), tutormyri bug (Brevennia rehi), etc. Pseudococcidae (Pseudococcidae); rioza erytreae), Cacopsylla pyrisuga, Cacopsylla prairie (Cacopsylla chinensis), Phytopathidae (Bacterica cockerelli), Pear psylla (Cacopsylla pyricola), etc. Chytichcha marmorata), Stephanitis nashi, Tuftiidae (Stephanitis pyrioides), etc. (Tingidae); .

鱗翅目害虫(Lepidoptera):ニカメイガ(Chilo suppressalis)、Darkheaded stem borer(Chilo polychrysus)、White stem borer(Scirpophaga innotata)、イッテンオオメイガ(Scirpophaga incertulas)、Rupela albina、コブノメイガ(Cnaphalocrocis medinalis)、Marasmia patnalis、イネハカジノメイガ(Marasmia exigua)、ワタノメイガ(Notarcha derogata)、アワノメイガ(Ostrinia furnacalis)、European corn borer(Ostrinia nubilalis)、ハイマダラノメイガ(Hellula undalis)、モンキクロノメイガ(Herpetogramma luctuosale)、シバツトガ(Pediasia teterrellus)、ライスケースワーム(Nymphula depunctalis)、Sugarcane borer(Diatraea saccharalis)等のツトガ科(Crambidae);モロコシマダラメイガ(Elasmopalpus lignosellus)、ノシメマダラメイガ(Plodia interpunctella)等のメイガ科(Pyralidae);ハスモンヨトウ(Spodoptera litura)、シロイチモジヨトウ(Spodoptera exigua)、アワヨトウ(Mythimna separata)、ヨトウガ(Mamestra brassicae)、イネヨトウ(Sesamia inferens)、シロナヨトウ(Spodoptera mauritia)、フタオビコヤガ(Naranga aenescens)、ツマジロクサヨトウ(Spodoptera frugiperda)、アフリカシロナヨトウ(Spodoptera exempta)、タマナヤガ(Agrotis ipsilon)、タマナギンウワバ(Autographa nigrisigna)、イネキンウワバ(Plusia festucae)、Soybean looper(Chrysodeixis includens)、トリコプルシア属(Trichoplusia spp.)、ニセアメリカタバコガ(Heliothis virescens)等ヘリオティス属、オオタバコガ(Helicoverpa armigera)、アメリカタバコガ(Helicoverpa zea)等ヘリコベルパ属、Velvetbean caterpillar(Anticarsia gemmatalis)、Cotton leafworm(Alabama argillacea)、Hop vine borer(Hydraecia immanis)等のヤガ科(Noctuidae);モンシロチョウ(Pieris rapae)等のシロチョウ科(Pieridae);ナシヒメシンクイ(Grapholita molesta)、スモモヒメシンクイ(Grapholita dimorpha)、マメシンクイガ(Leguminivora glycinivorella)、アズキサヤムシガ(Matsumuraeses azukivora)、リンゴコカクモンハマキ(Adoxophyes orana fasciata)、チャノコカクモンハマキ(Adoxophyes honmai)、チャハマキ(Homona magnanima)、ミダレカクモンハマキ(Archips fuscocupreanus)、コドリンガ(Cydia pomonella)、カンシャシンクイハマキ(Tetramoera schistaceana)、Bean Shoot Borer(Epinotia aporema)、Citrus fruit borer(Ecdytolopha aurantiana)等のハマキガ科(Tortricidae);チャノホソガ(Caloptilia theivora)、キンモンホソガ(Phyllonorycter ringoniella)のホソガ科(Gracillariidae);モモシンクイガ(Carposina sasakii)等のシンクイガ科(Carposinidae);Coffee Leaf miner(Leucoptera coffeel
la)、モモハモグリガ(Lyonetia clerkella)、ギンモンハモグリガ(Lyonetia prunifoliella)等のハモグリガ科(Lyonetiidae);マイマイガ(Lymantria dispar)等リマントリア属、チャドクガ(Euproctis pseudoconspersa)等ユープロクティス属等のドクガ科(Lymantriidae);コナガ(Plutella xylostella)等のコナガ科(Pluteliidae);モモキバガ(Anarsia lineatella)、イモキバガ(Helcystogramma triannulellum)、ワタアカミムシガ(Pectinophora gossypiella)、ジャガイモガ(Phthorimaea operculella)、Tuta absoluta等のキバガ科(Gelechiidae);アメリカシロヒトリ(Hyphantria cunea)等のヒトリガ科(Arctiidae);Giant Sugarcane borer(Telchin licus)等のカストニアガ科(Castniidae);ヒメボクトウ(Cossus insularis)等のボクトウガ科(Cossidae);ヨモギエダシャク(Ascotis selenaria)等のシャクガ科(Geometridae);ヒロヘリアオイラガ(Parasa lepida)等のイラガ科(Limacodidae);カキノヘタムシガ(Stathmopoda masinissa)等のニセマイコガ科(Stathmopodidae);クロメンガタスズメ(Acherontia lachesis)等のスズメガ科(Sphingidae);キクビスカシバ(Nokona feralis)等のスカシバガ科(Sesiidae);イネツトムシ(Parnara guttata)等のセセリチョウ科(Hesperiidae)。
Lepidoptera insects (Lepidoptera): Nymphs (Chilo suppressalis), Darkheaded stem borer (Chilo polychrysus), White stem borer (Scirpophaga innotata), Itten's tree magnolia (Scirpophaga incertulas), Rupela albina, Kobomeiga (Cinatalitraceitraceitracel Red clover (Marasmia exigua), cotton dwarf (Notarcha derogata), African dwarf (Ostrinia furnacalis), European corn borer (Ostrinia nubilalis), black-legged moth (Hellula undulis), Monquil chronogare (Herpetogramma luctigueta) Rice case worms (Nymphula depunctalis), Sugarcane borer (Diatraea saccharalis), etc. (Cambididae); , Roy Spurge (Spodoptera exigua), Sturgeon (Mythimna separata), Sparrow (Mamestra brassicae), Spurge (Sesamia inferens), Spodoptera mauritia, Phylum oryzae (Naranga aenescens), Spurges exempta), spiny moth (Agrotis ipsilon), spiny eel (Autographa nigrisigna), inykin owava (Plusia festucae), Soybean looper (Chrysodeixis includens), Trichoplusia spp. Helicoverpa armigera), Helicoverpa zea etc. Helicoverpa, Velvetbean caterpillar (Anticarsia gemmatalis), Cotton leafworm (Alabama argillacea), Hop vine borer (Hydraecia immanis) etc. Yagidae (Noctuiipalis); Pae) et al. (Pieridae); Anemonefish (Grapholita molesta), Anemonefish (Grapholita dimorpha), Leguminivora (Leguminivora glycinivorella), Azukisya Mushiga (Matsumuraeses azukivora), Anemone parrotfish (Adoxophycha or Hamaki (Adoxophyes honmai), Chahamaki (Homona magnanima), Midarekamonhamaki (Archips fuscocupreanus), codling moth (Cydia pomonella), Kanshashini Hamami (Tetramoera schistaceana), Bean Shoot Borer (Epinotia aporema) luciferitracit And the like (Coroptilia theivora), and the moth family (Gracillariidae) of the dog moth (Phyllonorycter ringoniella);
(Lyonetia clerkella, Lyonetia prunifoliella, etc .; Lyonetidae); Lymantria dispar, etc. Lymantria, Euproctis pseudoconspersa, etc. ; Pluteliidae such as Plutella xylostella; Pectinidae (Anarsia lineatella); Firefly (Hyphantria cunea) et al. (Arctiidae); Giant Sugarcane borer (Telchin licus) et al. (Castniidae); Family (Geometridae) Black-tailed lizards (Limacodidae) such as Parasa lepida; False-tailed Moths (Stathmopodidae) such as Stathumopoda masinissa, etc .; Sphingidae (Sphingidae) such as Acherontia lachesis; Sevisiidae (Sesiidae); Hesperiidae (Hesperiidae), such as the ladybug Parnara guttata.

総翅目害虫(Thysanoptera):ミカンキイロアザミウマ(Frankliniella occidentalis)、ミナミキイロアザミウマ(Thrips palmi)、チャノキイロアザミウマ(Scirtothrips dorsalis)、ネギアザミウマ(Thrips tabaci)、ヒラズハナアザミウマ(Frankliniella intonsa)、イネアザミウマ(Stenchaetothrips biformis)、モトジロアザミウマ(Echinothrips americanus)等のアザミウマ科(Thripidae);イネクダアザミウマ(Haplothrips aculeatus)等のクダアザミウマ科(Phlaeothripidae)。   Thysanoptera: Thripsidae (Frankliniella occidentalis), Thrips palmi (Thrips palmi), Chalyss occidentalis (Scirtothrips dorsalis), Locustoids (Thrips tabaci), Philosophis japonicus (Frankliniella intimasite) And Thripidae such as Echinothrips americanus); Thripidae (Phlaeothripidae) such as Haekohrrips aculeatus.

双翅目害虫(Diptera):タネバエ(Delia platura)、タマネギバエ(Delia antiqua)等のハナバエ科(Anthomyiidae);シュガービートルートマゴット(Tetanops myopaeformis)等のハネフリバエ科(Ulidiidae);イネハモグリバエ(Agromyza oryzae)、トマトハモグリバエ(Liriomyza sativae)、マメハモグリバエ(Liriomyza trifolii)、ナモグリバエ(Chromatomyia horticola)等のハモグリバエ科(Agromyzidae);イネキモグリバエ(Chlorops oryzae)等のキモグリバエ科(Chloropidae);ウリミバエ(Bactrocera cucurbitae)、ミカンコミバエ(Bactrocera dorsalis)、ナスミバエ(Bactrocera latifrons)、オリーブミバエ(Bactrocera oleae)、クインスランドミバエ(Bactrocera tryoni)、チチュウカイミバエ(Ceratitis capitata)等のミバエ科(Tephritidae);イネヒメハモグリバエ(Hydrellia griseola)、トウヨウイネクキミギワバエ(Hydrellia philippina)、イネクキミギワバエ(Hydrellia sasakii)等のミギワバエ科(Ephydridae);オウトウショウジョウバエ(Drosophila suzukii)等のショウジョウバエ科(Drosophilidae);オオキモンノミバエ(Megaselia spiracularis)等のノミバエ科(Phoridae);オオチョウバエ(Clogmia albipunctata)等のチョウバエ科(Psychodidae);チビクロバネキノコバエ(Bradysia difformis)等のクロバネキノコバエ科(Sciaridae);ヘシアンバエ(Mayetiola destructor)、イネノシントメタマバエ(Orseolia oryzae)等のタマバエ科(Cecidomyiidae);Diopsis macrophthalma等のシュモクバエ科(Diopsidae);キリウジガガンボ(Tipula aino)、Common cranefly(Tipula oleracea)、European cranefly(Tipula paludosa)等のガガンボ科(Tipulidae)。   Diptera: Insect fly (Delia platura), Onion fly (Delia antiqua), etc. Anthomyiidae; Sugar beet rooted magots (Tetanops myopaeformis), etc. A family of freshwater flies such as the tomato leafminer fly (Liriomyza sativae), a bean leafminer fly (Liliomyza trifolii), a leafminer fly (Chromatomyia horticola), and the like; Fruit fly (Bactrocera latifrons), olive fruit fly (Bactrocera oleae), quince fruit fly (Bactrocera tryoni), fruit fly (Ceratitis capitata) and other fruit flies (Tephritidae); Phylogenidae (Ephydridae) such as Hydrellia philippina, Hydrellia sasakii etc .; Drosophila family such as Drosophila melanogaster (Drosophila suzukii); ; Phylogenidae (Psychodidae), such as the great butterfly fly (Clogmia albipunctata); Spermidae (Sciaridae), such as the fly Shrimp (Bradysia divormis), etc .; (Cecidomyiidae); Diopsidae (Diopsidae) such as Diopsis macrophthalma etc .; and Gagobo family (Tipulidae) such as Common cranefly (Tipula oleracea), European cranefly (Tipula paludosa) etc.

鞘翅目害虫(Coleoptera):ウエスタンコーンルートワーム(Diabrotica virgifera virgifera)、サザンコーンルートワーム(Diabrotica undecimpunctata howardi)、ノザンコーンルートワーム(Diabrotica barberi)、メキシカンコーンルートワーム(Diabrotica virgifera zeae)、バンデッドキューカンバービートル(Diabrotica balteata)、Cucurbit Beetle(Diabrotica speciosa)、ビーンリーフビートル(Cerotoma trifurcata)、クビアカクビホソハムシ(Oulema melanopus)、ウリハムシ(Aulacophora femoralis)、キスジノミハムシ(Phyllotreta striolata)、コロラドハムシ(Leptinotarsa decemlineata)、イネドロオイムシ(Oulema oryzae)、グレープ・コラスピス(Colaspis brunnea)、コーン・フレアビートル(Chaetocnema pulicaria)、サツマイモヒサゴトビハムシ(Chaetocnema confnis)、ポテト・フレアビートル(Epitrix cucumeris)、イネトゲハムシ(Dicladispa armigera)、Grape Colaspis(Colaspis brunnea)、southern corn leaf beetle(Myochrous denticollis)、ヨツモンカメノコハムシ(Laccoptera quadrimaculata)、タバコノミハムシ(Epitrix hirtipennis)等のハムシ科(Chrysomelidae);Seedcorn beetle(Stenolophus lecontei)、Slender seedcorn beetle(Clivina impressifrons)等のオサムシ科(Carabidae);ドウガネブイブイ(Anomala cuprea)、ヒメコガネ(Anomala rufocuprea)、アオドウガネ(Anomala albopilosa)、マメコガネ(Popillia japonica)、ナガチャコガネ(Heptophylla picea)、European Chafer(Rhizotrogus majalis)、クロマルコガネ(Tomarus gibbosus)、Holotrichia属(Holotrichia spp.)、ジューン・ビートル(Phyllophaga crinita)等Phyllophaga属(Phyllophaga spp.)等のコガネムシ科(Scarabaeidae);ワタミヒゲナガゾウムシ(Araecerus coffeae)、アリモドキゾウムシ(Cylas formicarius)、イモゾウムシ(Euscepes postfasciatus)、アルファルファタコゾウムシ(Hypera postica)、コクゾウムシ(Sitophilus zeamais)、イネゾウムシ(Echinocnemus squameus)、イネミズゾウムシ(Lissorhoptrus oryzophilus)、シロスジオサゾウムシ(Rhabdoscelus lineatocollis)、ワタミハナゾウムシ(Anthonomus grandis)、シバオサゾウムシ(Sphenophorus venatus)、Southern Corn Billbug(Sphenophorus callosus)、Soybean stalk weevil(Sternechus subsignatus)、Sugarcane weevil(Sphenophorus levis)、サビヒョウタンゾウムシ(Scepticus griseus)、トビイロヒョウタンゾウムシ(Scepticus uniformis)、ブラジルマメゾウムシ(Zabrotes subfasciatus)、マツノキクイムシ(Tomicus piniperda)、Coffee Berry Borer(Hypothenemus hampei)等のゾウムシ科(Curculionidae);コクヌストモドキ(Tribolium castaneum)、ヒラタコクヌストモドキ(Tribolium confusum)等のゴミムシダマシ科(Tenebrionidae);ニジュウヤホシテントウ(Epilachna vigintioctopunctata)等のテントウムシ科(Coccinellidae);ヒラタキクイムシ(Lyctus brunneus)等のナガシンクイムシ科(Bostrychidae);ヒョウホンムシ科(Ptinidae);ゴマダラカミキリ(Anoplophora malasiaca)、Migdolus fryanus等のカミキリムシ科(Cerambycidae);オキナワカンシャクシコメツキ(Melanotus okinawensis)、トビイロムナボソコメツキ(Agriotes fuscicollis)、クシコメツキ(Melanotus legatus)、アシブトコメツキ属(Anchastus spp.)、コノデルス属(Conoderus spp.)、クテニセラ属(Ctenicera spp.)、リモニウス属(Limonius spp.)、Aeolus属(Aeolus spp.)等のコメツキムシ科(Agriotes sp.、Aelous sp.、Anchastus sp.、Melanotus sp.、Limonius sp.、Conoderus sp.、Ctenicera sp.);アオバアリガタハネカクシ(Paederus fuscipes)等のハネカクシ科(Staphylinidae)。   Coleoptera insect pest (Coleoptera): Western corn rootworm (Diabrotica virgifera virgifera), Southern corn rootworm (Diabrotica undecimpunctata howardi), Northern corn rootworm (Diabrotica barberi), Mexican corn rootworm (Diabrotica virgifera zeae), Banded Cucumber Beetle (Diabrotica virgifera zeae) Diabrotica balteata), Cucurbit Beetle (Diabrotica speciosa), Bean Leaf Beetle (Cerotoma trifurcata), Cubial Leaf Beetle (Oulema melanopus), Ground Leaf Beetle (Aulacophora femoralis), Sweet potato leaf beetle (Phyllo tta striola ate leaves) Oulema oryzae), grape coraspis (Colaspis brunnea), corn flare beatle (Chaetocnema pulicaria), sweet potato leaf beetle (Chaetocnema confnis), potato flare beatle (Epitrix cuc) umeris), green leaf beetle (Dicladispa armigera), Grape Colaspis (Colaspis brunnea), southern corn leaf beetle (Myochrous denticollis), pokeweed leaf beetle (Laccoptera quadrimaculata), tobacco leaf beetle (Epitrix hirtipilichidae) Carabidae (Carabidae), such as (Stenolophus lecontei), Slender seedcorn beetle (Clivina impressifrons); Scarabaeidae (Scarabaeidae) such as European Chafer (Rhizotrogus majalis), Black-tailed Beetle (Tomarus gibbosus), Holotrichia sp. coffeae), Arimo Weeping beetle (Cylas formicarius), potato weevil (Euscepes postfasciatus), alfalfa bug (Hypera postica), caterpillar (Sitophilus zeamais), rice weevil (Echinocnemus squameus), rice weevil (Lissoroptrus oryzophilus citivius) Anthonomus grandis), Sphenophorus venatus, Southern Corn Billbug (Sphenophorus callosus), Soyabean stalk weevil (Sternechus subsignatus), Sugarcane weevil (Sphenophorus levis), Sabiphos gossipius ), Brazilian weevil (Zabrotes subfasciatus), Pinus bovis (Tomicus piniperda), Coffee Berry (Hypothenemus hampei) and other weevil families (Curculionidae); Red-tailed beetle (Tribolium confusum) and other beetles (Tenebrionidae); Epilachna vigintioctopunctata such as ladybirds (Coccinellidae); Ptinidae); Longhorn beetles (Anoplophora malasiaca), Migdolus fryanus, etc., Cerambycididae (Cerambycidae); spp., Conoderus spp., Ctenicera spp., Limonius sp., Aeolus sp., and other clickworms (Agriotes sp., Aelous sp., Anchastus sp.) , Melanotus sp., Limonius sp., Conoderus sp., Ctenicera sp.); Staphylinidae (Staphylinidae), such as Paederus fuscipes.

直翅目害虫(Orthoptera):トノサマバッタ(Locusta migratoria)、モロッコトビバッタ(Dociostaurus maroccanus)、オーストラリアトビバッタ(Chortoicetes terminifera)、アカトビバッタ(Nomadacris septemfasciata)、Brown Locust(Locustana pardalina)、Tree Locust(Anacridium melanorhodon)、Italian Locust(Calliptamus italicus)、Differential grasshopper(Melanoplus differentialis)、Two striped grasshopper(Melanoplus bivittatus)、Migratory grasshopper(Melanoplus sanguinipes)、Red-Legged grasshopper(Melanoplus femurrubrum)、Clearwinged grasshopper(Camnula pellucida)、サバクワタリバッタ(Schistocerca gregaria)、Yellow-winged locust(Gastrimargus musicus)、Spur-throated locust(Austracris guttulosa)、コバネイナゴ(Oxya yezoensis)、ハネナガイナゴ(Oxya japonica)、タイワンツチイナゴ(Patanga succincta)等のバッタ科(Acrididae);ケラ(Gryllotalpaorientalis)等のケラ科(Gryllotalpidae);ヨーロッパイエコオロギ(Acheta domesticus)、エンマコオロギ(Teleogryllus emma)等のコオロギ科(Gryllidae);Mormon cricket(Anabrus simplex)等のキリギリス科(Tettigoniidae)。
膜翅目害虫(Hymenoptera):カブラハバチ(Athalia rosae)、ニホンカブラバチ(Athalia japonica)等のハバチ科(Tenthredinidae);ファイヤーアント(Solenopsis spp.)科、Brown leaf-cutting ant(Atta capiguara)等のアリ科(Formicidae)等。
Orthopteran pests (Orthoptera): Toocta grasshopper (Locusta migratoria), Toroca grasshopper (Dociostaurus maroccanus), Australian Tobibatata (Chortoicetes terminifera), Red-footed grasshopper (Nomadacris septemfasciata), Brown Locust (Locustana pallitalucilatio) Italian Locust (Calliptamus italicus), Differential grasshopper (Melanoplus differentialis), Two striped grasshopper (Melanoplus bivittatus), Migratory grasshopper (Melanoplus sanguinipelus), Red-Legged grasshopper (Melh gregaria), Yellow-winged locust (Gastrimargus musicus), Spur-throated locust (Austracris guttulosa), Kobayinago (Oxya yezoensis), Hanekinago (Oxya japonica), Trichoderma japonicus (Patanga succi nectiograms), etc. arientalis) et al. (Gryllotalpidae); European green cricket (Acheta domesticus), Erick's eagle (Teleogrylus emma) et al. (Gryllidae); Mormon cricket (Anabrus simplex) et al.
Hymenoptera pests (Hymenoptera): Aphididae (Athalia rosae), Japanese wasps (Athalia japonica) and other species of the Japanese wasp (Tenthredinidae); Family (Formicidae) etc.

ゴキブリ目害虫(Blattodea):チャバネゴキブリ(Blattella germanica)等のチャバネゴキブリ科(Blattellidae);クロゴキブリ(Periplaneta fuliginosa)、ワモンゴキブリ(Periplaneta americana)、トビイロゴキブリ(Periplaneta brunnea)、トウヨウゴキブリ(Blatta orientalis)等のゴキブリ科(Blattidae);ヤマトシロアリ(Reticulitermes speratus)、イエシロアリ(Coptotermes formosanus)、アメリカカンザイシロアリ(Incisitermes minor)、ダイコクシロアリ(Cryptotermes domesticus)、タイワンシロアリ(Odontotermes formosanus)、コウシュンシロアリ(Neotermes koshunensis)、サツマシロアリ(Glyptotermes satsumensis)、ナカジマシロアリ(Glyptotermes nakajimai)、カタンシロアリ(Glyptotermes fuscus)、オオシロアリ(Hodotermopsis sjostedti)、コウシュウイエシロアリ(Coptotermes guangzhouensis)、アマミシロアリ(Reticulitermes amamianus)、ミヤタケシロアリ(Reticulitermes miyatakei)、カンモンシロアリ(Reticulitermes kanmonensis)、タカサゴシロアリ(Nasutitermes takasagoensis)、ニトベシロアリ(Pericapritermes nitobei)、ムシャシロアリ(Sinocapritermes mushae)、Cornitermes cumulans等のシロアリ科(Termitidae)等。   Cockroach second order (Blattodea): German cockroach (Blattella germanica) and other German cockroaches (Blattellidae); Family (Blattidae); Yamato termites (Reticulitermes speratus), house termites (Coptotermes formosanus), American termites (Incisitermes minor), Dicta termites (Cryptotermes domesticus), Taiwan termites (Odontotermes formosanus), White-spotted termites (Glyptotermes satsumensis), Chinese termite (Glyptotermes nakajimai), Catan termite (Glyptotermes fuscus), Oolongtermite (Hodotermopsis sjostedti), Gl. Loari (Reticulitermes amamianus), Miyatake termite (Reticulitermes miyatakei), Cameroon termite (Reticulitermes kanmonensis), Takasago termite (Nasutitermes takasagoensis), Nitobe termite (Pericapritermes nitobei), Musashi termi (Sinocapritimates) )etc.

以下に製造例、参考製造例、製剤例及び試験例を示して、本発明をより具体的に説明するが、本発明はこれらの例に限定されない。   The present invention will be more specifically described below with reference to production examples, reference production examples, formulation examples and test examples, but the present invention is not limited to these examples.

製造例1−1
室温で、参考製造例1に記載の中間体(A1a1)1.7g、N,N−ジメチルホルムアミド20mL及びピリジン1.4mLの混合物に、トリフルオロ酢酸無水物1.4mLを加えた後、80℃で6時間加熱撹拌した。その後、室温で水20mLを加え、酢酸エチルで抽出し、有機層を2N塩酸で洗浄後、有機層を乾燥、減圧濃縮した。得られた残渣をシリカゲルカラムクロマトグラフィー(ヘキサン:酢酸エチル=4:1)に付し、下記で示される本発明化合物1を1.8g得た。

Figure 2019089711
本発明化合物1:1H-NMR (CDCl3) δ: 8.09-8.06 (2H, m), 7.48-7.46 (2H, m), 3.73 (2H, s), 2.01 (3H, s). Production Example 1-1
After adding 1.4 mL of trifluoroacetic anhydride to a mixture of 1.7 g of the intermediate (A1a1) described in Reference Production Example 1, 20 mL of N, N-dimethylformamide and 1.4 mL of pyridine at room temperature, 80 ° C. The mixture was heated and stirred for 6 hours. Thereafter, 20 mL of water was added at room temperature, extraction was performed with ethyl acetate, the organic layer was washed with 2N hydrochloric acid, and the organic layer was dried and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography (hexane: ethyl acetate = 4: 1) to obtain 1.8 g of the present compound 1 shown below.
Figure 2019089711
The present compound 1: 1 H-NMR (CDCl 3 ) δ: 8.09-8.06 (2H, m), 7.48-7.46 (2H, m), 3.73 (2H, s), 2.01 (3H, s).

製造例1−2
製造例1−1に記載の方法に準じて製造した本発明化合物と、その物性値を以下に示す。
式(1a)

Figure 2019089711
で示される化合物において、R8、R9及びR10の組合わせが[表1]に記載のいずれかの組合せである化合物。
[表1]
Figure 2019089711
本発明化合物19:1H-NMR (CDCl3) δ: 8.08-8.06 (2H, m), 7.49-7.47 (2H, m), 3.78 (2H, s), 2.48-2.43 (2H, m), 1.27-1.22 (3H, m).
本発明化合物33:1H-NMR (CDCl3) δ: 8.07-8.05 (2H, m), 7.50-7.49 (2H, m), 3.80 (2H, s), 2.83-2.78 (1H, m), 1.27 (6H, d, J = 6.5 Hz).
本発明化合物34:1H-NMR (CDCl3) δ: 8.13-8.10 (2H, m), 7.53-7.51 (2H, m), 4.18 (2H, s). Production Example 1-2
The compound of the present invention manufactured according to the method described in Production Example 1-1 and the physical properties thereof are shown below.
Formula (1a)
Figure 2019089711
In the compounds shown by, the combination of R 8 , R 9 and R 10 is any combination described in [Table 1].
[Table 1]
Figure 2019089711
The present compound 19: 1 H-NMR (CDCl 3 ) δ: 8.08-8.06 (2H, m), 7.49-7.47 (2H, m), 3.78 (2H, s), 2.48-24.43 (2H, m), 1.27 -1.22 (3H, m).
The present compound 33: 1 H-NMR (CDCl 3 ) δ: 8.07-8.05 (2H, m), 7.50-7.49 (2H, m), 3.80 (2H, s), 2.83-2 2.78 (1H, m), 1.27 (6H, d, J = 6.5 Hz).
Invention compound 34: 1 H-NMR (CDCl 3 ) δ: 8.13-8.10 (2H, m), 7.53-7.51 (2H, m), 4.18 (2H, s).

式(1b)

Figure 2019089711
で示される化合物において、R8、R9及びR10の組合わせが[表2]に記載の組合せである化合物。
[表2]
Figure 2019089711
本発明化合物2:1H-NMR (CDCl3) δ: 8.06-8.05 (1H, m), 8.02-8.00 (1H, m), 7.55-7.53 (1H, m), 7.50-7.48 (1H, m), 3.75 (2H, s), 2.02 (3H, s). Formula (1b)
Figure 2019089711
In the compounds shown by, the combination of R 8 , R 9 and R 10 is a combination described in [Table 2].
[Table 2]
Figure 2019089711
The present compound 2: 1 H-NMR (CDCl 3 ) δ: 8.06-8.05 (1H, m), 8.02-8.00 (1H, m), 7.55-7.53 (1H, m), 7.50-7.48 (1H, m) , 3.75 (2H, s), 2.02 (3H, s).

式(1c)

Figure 2019089711
で示される化合物において、R8、R9、R10、R21及びR22の組合わせが[表3]に記載のいずれかの組合せである化合物。
[表3]
Figure 2019089711
本発明化合物3:1H-NMR (CDCl3) δ: 8.20-8.17 (2H, m), 7.61-7.60 (2H, m), 4.34 (2H, s), 2.84 (3H, s).
本発明化合物21:1H-NMR (CDCl3) δ: 8.03-8.01 (1H, m), 7.95-7.93 (1H, m), 7.71-7.68 (1H, m), 4.40 (2H, s), 2.89 (3H, s).
本発明化合物22:1H-NMR (CDCl3) δ: 8.18-8.14 (1H, m), 7.42-7.39 (2H, m), 4.33 (2H, s), 2.88 (3H, s). Formula (1c)
Figure 2019089711
Compounds in which R 8 , R 9 , R 10 , R 21 and R 22 are in any combination described in [Table 3].
[Table 3]
Figure 2019089711
The present compound 3: 1 H-NMR (CDCl 3 ) δ: 8.20-8.17 (2H, m), 7.61-7.60 (2H, m), 4.34 (2H, s), 2.84 (3H, s).
The present compound 21: 1 H-NMR (CDCl 3 ) δ: 8.03-8.01 (1H, m), 7.95-7.93 (1H, m), 7.71-7.68 (1H, m), 4.40 (2H, s), 2.89 (3H, s).
Invention compound 22: 1 H-NMR (CDCl 3 ) δ: 8.18-8.14 (1H, m), 7.42-7.39 (2H, m), 4.33 (2H, s), 2.88 (3H, s).

式(1d)

Figure 2019089711
で示される化合物において、R8、R9及びR10の組合わせが[表4]に記載の組合せである化合物。
[表4]
Figure 2019089711
本発明化合物4:1H-NMR (CDCl3) δ: 8.19 (1H, dt), 8.16-8.16 (1H, m), 7.68 (1H, dt), 7.63-7.60 (1H, m), 4.35 (2H, s), 2.85 (3H, s). Formula (1d)
Figure 2019089711
In the compounds shown by, the combination of R 8 , R 9 and R 10 is a combination described in [Table 4].
[Table 4]
Figure 2019089711
The present compound 4: 1 H-NMR (CDCl 3 ) δ: 8.19 (1 H, dt), 8.16-8.16 (1 H, m), 7.68 (1 H, dt), 7.63-7.60 (1 H, m), 4.35 (2 H) , s), 2.85 (3H, s).

式(1e)

Figure 2019089711
で示される化合物において、R6、R8、R9及びR10の組合わせが[表5]に記載のいずれかの組合せである化合物。
[表5]
Figure 2019089711
本発明化合物5:1H-NMR (CDCl3) δ: 8.13 (2H, d, J = 8.2 Hz), 7.53 (2H, d, J = 8.2 Hz), 4.72 (1H, s), 4.43 (2H, d, J = 6.1 Hz), 2.94 (3H, s).
本発明化合物23:1H-NMR (CDCl3) δ: 8.14-8.12 (2H, m), 7.54-7.52 (2H, m), 4.64 (1H), 4.40 (2H, d), 3.02 (2H, q), 1.37 (3H, t).
本発明化合物24:1H-NMR (CDCl3) δ: 8.14-8.11 (2H, m), 7.54-7.52 (2H, m), 4.42 (3H, s), 3.14 (1H, t), 1.40 (6H, d).
本発明化合物25:1H-NMR (CDCl3) δ: 8.13-8.11 (2H, m), 7.56-7.53 (2H, m), 4.72 (1H, t), 4.44 (2H, d, J = 6.4 Hz), 2.42-2.35 (1H, m), 1.20-1.16 (2H, m), 0.99-0.94 (2H, m).
本発明化合物35:1H-NMR (CDCl3) δ: 8.14-8.11 (2H, m), 7.53-7.51 (2H, m), 4.46 (1H, br s), 4.40 (2H, d), 2.99-2.95 (2H, m), 1.88-1.82 (2H, m), 1.03 (3H, t).
本発明化合物36:1H-NMR (CDCl3) δ: 8.13-8.11 (2H, m), 7.52 (2H, d), 4.69 (1H, t), 4.40 (2H, d), 3.00-2.96 (2H, m), 1.82-1.74 (2H, m), 1.47-1.37 (2H, m), 0.92 (3H, t).
本発明化合物37:1H-NMR (CDCl3) δ: 8.12 (2H, d), 7.52 (2H, d), 4.72 (1H, t), 4.39 (2H, d), 2.90-2.88 (2H, m), 2.30-2.20 (1H, m), 1.08 (6H, d).
本発明化合物38:1H-NMR (DMSO-D6) δ: 8.06-8.04 (2H, m), 7.80 (1H, s), 7.56-7.54 (2H, m), 7.39-7.37 (5H, m), 4.38 (2H, s), 4.20 (2H, s).
本発明化合物39:1H-NMR (CDCl3) δ: 8.13-8.10 (2H, m), 7.58-7.56 (2H, m), 4.51 (2H, s), 2.86 (3H, s), 2.42-2.37 (1H, m), 0.87-0.82 (2H, m), 0.81-0.76 (2H, m).
本発明化合物40:1H-NMR (CDCl3) δ: 8.03-8.01 (2H, m), 7.44 (2H, d, J = 8.2 Hz), 7.36-7.32 (2H, m), 7.30-7.26 (3H, m), 4.93 (2H, s), 2.99 (3H, s).
本発明化合物41:1H-NMR (CDCl3) δ: 8.04-8.01 (2H, m), 7.40-7.37 (2H, m), 7.24-7.15 (4H, m), 4.85 (1H, br s), 4.72 (1H, br s), 3.00 (3H, s), 2.14 (3H, s).
本発明化合物42:1H-NMR (CDCl3) δ: 8.04-8.01 (2H, m), 7.44 (2H, d), 7.23-7.19 (1H, m), 7.10-7.06 (3H, m), 4.91 (2H, s), 2.98 (3H, s), 2.31 (3H, s).
本発明化合物43:1H-NMR (CDCl3) δ: 8.04-8.01 (2H, m), 7.44 (2H, d), 7.16-7.11 (4H, m), 4.90 (2H, s), 2.97 (3H, s), 2.30 (3H, s).
本発明化合物44:1H-NMR (CDCl3) δ: 8.03-8.01 (2H, m), 7.45 (2H, d), 7.32-7.28 (1H, m), 7.20-7.11 (2H, m), 7.07-7.02 (1H, m), 4.88 (2H, s), 3.06 (3H, s).
本発明化合物45:1H-NMR (CDCl3) δ: 8.02-8.00 (2H, m), 7.44 (2H, d), 7.29-7.25 (1H, m), 7.10-7.08 (1H, m), 6.95-6.93 (1H, m), 6.85-6.80 (1H, m), 4.85 (2H, br s), 3.93 (3H, s), 3.02 (3H, s).
本発明化合物46:1H-NMR (CDCl3) δ: 8.09 (2H, d), 7.57 (2H, d), 4.61 (2H, s), 3.02 (3H, s), 1.46 (9H, s)
本発明化合物90:1H-NMR (CDCl3) δ: 8.10 (2H, d), 7.56 (2H, d), 4.44 (2H, s), 4.26-4.35 (1H, m), 2.91 (3H, s), 1.84-1.91 (2H, m), 1.43-1.75 (6H, m)
本発明化合物91:1H-NMR (CDCl3) δ: 8.09 (2H, d), 7.57 (2H, d), 4.46 (2H, s), 3.69-3.77 (1H, m), 2.88 (3H, s), 1.71-1.81 (4H, m), 1.55-1.63 (1H, m), 1.25-1.41 (4H, m), 0.95-1.05 (1H, m)
本発明化合物92:1H-NMR (CDCl3) δ: 8.14-8.11 (2H, m), 7.56-7.54 (2H, m), 4.51 (2H, s), 3.43-3.39 (2H, m), 2.98 (3H, s), 2.60-2.56 (2H, m), 2.06 (3H, s). Formula (1e)
Figure 2019089711
In the compounds shown by, the combination of R 6 , R 8 , R 9 and R 10 is any combination described in [Table 5].
[Table 5]
Figure 2019089711
The present compound 5: 1 H-NMR (CDCl 3 ) δ: 8.13 (2H, d, J = 8.2 Hz), 7.53 (2H, d, J = 8.2 Hz), 4.72 (1 H, s), 4.43 (2 H, d, J = 6.1 Hz), 2.94 (3 H, s).
The present compound 23: 1 H-NMR (CDCl 3 ) δ: 8.14-8.12 (2H, m), 7.54-7.52 (2H, m), 4.64 (1H), 4.40 (2H, d), 3.02 (2H, q) ), 1.37 (3H, t).
The present compound 24: 1 H-NMR (CDCl 3 ) δ: 8.14-8.11 (2H, m), 7.54-7.52 (2H, m), 4.42 (3H, s), 3.14 (1H, t), 1.40 (6H , d).
The present compound 25: 1 H-NMR (CDCl 3 ) δ: 8.13-8.11 (2H, m), 7.56-7.53 (2H, m), 4.72 (1H, t), 4.44 (2H, d, J = 6.4 Hz ), 2.42-2.35 (1 H, m), 1.20-1. 16 (2 H, m), 0.99-0.94 (2 H, m).
The present compound 35: 1 H-NMR (CDCl 3 ) δ: 8.14-8.11 (2H, m), 7.53-7.51 (2H, m), 4.46 (1H, br s), 4.40 (2H, d), 2.99- 2.95 (2H, m), 1.88-1.82 (2H, m), 1.03 (3H, t).
The present compound 36: 1 H-NMR (CDCl 3 ) δ: 8.13-8.11 (2H, m), 7.52 (2H, d), 4.69 (1H, t), 4.40 (2H, d), 3.00-2.96 (2H , m), 1.82-1.74 (2H, m), 1.47-1.37 (2H, m), 0.92 (3H, t).
The present compound 37: 1 H-NMR (CDCl 3 ) δ: 8.12 (2H, d), 7.52 (2H, d), 4.72 (1H, t), 4.39 (2H, d), 2.90-2.88 (2H, m) ), 2.30-2.20 (1 H, m), 1.08 (6 H, d).
Invention compound 38: 1 H-NMR (DMSO-D 6 ) δ: 8.06-8.04 (2H, m), 7.80 (1H, s), 7.56-7.54 (2H, m), 7.39-7.37 (5H, m) , 4.38 (2H, s), 4.20 (2H, s).
The present compound 39: 1 H-NMR (CDCl 3 ) δ: 8.13-8.10 (2H, m), 7.58-7.56 (2H, m), 4.51 (2H, s), 2.86 (3H, s), 2.42-2.37. (1H, m), 0.87-0.82 (2H, m), 0.81-0.76 (2H, m).
Invention compound 40: 1 H-NMR (CDCl 3 ) δ: 8.03-8.01 (2H, m), 7.44 (2H, d, J = 8.2 Hz), 7.36-7.32 (2H, m), 7.30-7.26 (3H , m), 4.93 (2H, s), 2.99 (3H, s).
The present compound 41: 1 H-NMR (CDCl 3 ) δ: 8.04-8.01 (2H, m), 7.40-7.37 (2H, m), 7.24-7.15 (4H, m), 4.85 (1H, br s), 4.72 (1H, br s), 3.00 (3H, s), 2.14 (3H, s).
Invention compound 42: 1 H-NMR (CDCl 3 ) δ: 8.04-8.01 (2H, m), 7.44 (2H, d), 7.23-7.19 (1H, m), 7.10-7.06 (3H, m), 4.91 (2H, s), 2.98 (3H, s), 2.31 (3H, s).
Invention compound 43: 1 H-NMR (CDCl 3 ) δ: 8.04-8.01 (2H, m), 7.44 (2H, d), 7.16-7.11 (4H, m), 4.90 (2H, s), 2.97 (3H , s), 2.30 (3H, s).
Invention compound 44: 1 H-NMR (CDCl 3 ) δ: 8.03-8.01 (2H, m), 7.45 (2H, d), 7.32-7.28 (1H, m), 7.20-7.11 (2H, m), 7.07 -7.02 (1 H, m), 4.88 (2 H, s), 3.06 (3 H, s).
Invention compound 45: 1 H-NMR (CDCl 3 ) δ: 8.02-8.00 (2H, m), 7.44 (2H, d), 7.29-7.25 (1H, m), 7.10-7.08 (1H, m), 6.95 -6.93 (1H, m), 6.85-6.80 (1H, m), 4.85 (2H, br s), 3.93 (3H, s), 3.02 (3H, s).
The present compound 46: 1 H-NMR (CDCl 3 ) δ: 8.09 (2H, d), 7.57 (2H, d), 4.61 (2H, s), 3.02 (3H, s), 1.46 (9H, s)
The present compound 90: 1 H-NMR (CDCl 3 ) δ: 8.10 (2H, d), 7.56 (2H, d), 4.44 (2H, s), 4.26-4.35 (1H, m), 2.91 (3H, s) ), 1.84-1.91 (2H, m), 1.43-1.75 (6H, m)
The present compound 91: 1 H-NMR (CDCl 3 ) δ: 8.09 (2H, d), 7.57 (2H, d), 4.46 (2H, s), 3.69-3.77 (1H, m), 2.88 (3H, s) ), 1.71-1.81 (4H, m), 1.55-1.63 (1 H, m), 1.25-1.41 (4 H, m), 0.95-1. 05 (1 H, m)
The present compound 92: 1 H-NMR (CDCl 3 ) δ: 8.14-8.11 (2H, m), 7.56-7.54 (2H, m), 4.51 (2H, s), 3.43-3.39 (2H, m), 2.98 (3H, s), 2.60-2.56 (2H, m), 2.06 (3H, s).

式(1f)

Figure 2019089711
で示される化合物において、R6、R8、R9及びR10の組合わせが[表6]に記載のいずれかの組合せである化合物。
[表6]
Figure 2019089711
本発明化合物6:1H-NMR (CDCl3) δ: 8.10-8.07 (2H, m), 7.61-7.60 (1H, m), 7.57-7.53 (1H, m), 4.78 (1H, s), 4.43 (2H, d), 2.95 (3H, s).
本発明化合物26:1H-NMR (CDCl3) δ: 8.10-8.06 (2H, m), 7.62-7.60 (1H, m), 7.57-7.53 (1H, m), 4.64 (1H, br s), 4.41 (2H, d), 3.02 (2H, q), 1.37 (3H, t).
本発明化合物27:1H-NMR (CDCl3) δ: 8.09-8.06 (2H, m), 7.62-7.60 (1H, m), 7.56-7.52 (1H, m), 4.50 (1H, br s), 4.42 (2H, d, J = 6.1 Hz), 3.18-3.12 (1H, m), 1.39 (6H, d).
本発明化合物28:1H-NMR (CDCl3) δ: 8.13-8.12 (1H, m), 8.08-8.06 (1H, m), 7.63-7.60 (1H, m), 7.56-7.52 (1H, m), 4.74 (1H, t), 4.45 (2H, d), 2.43-2.37 (1H, m), 1.21-1.16 (2H, m), 1.00-0.95 (2H, m). Formula (1f)
Figure 2019089711
In the compound shown by, a combination of R 6 , R 8 , R 9 and R 10 is any combination described in [Table 6].
[Table 6]
Figure 2019089711
The present compound 6: 1 H-NMR (CDCl 3 ) δ: 8.10-8.07 (2H, m), 7.61-7.60 (1H, m), 7.57-7.53 (1H, m), 4.78 (1H, s), 4.43 (2H, d), 2.95 (3H, s).
The present compound 26: 1 H-NMR (CDCl 3 ) δ: 8.10-8.06 (2H, m), 7.62-7.60 (1H, m), 7.57-7.53 (1H, m), 4.64 (1H, br s), 4.41 (2H, d), 3.02 (2H, q), 1.37 (3H, t).
The present compound 27: 1 H-NMR (CDCl 3 ) δ: 8.09-8.06 (2H, m), 7.62-7.60 (1H, m), 7.56-7.52 (1H, m), 4.50 (1H, br s), 4.42 (2 H, d, J = 6.1 Hz), 3.18-3.12 (1 H, m), 1. 39 (6 H, d).
The present compound 28: 1 H-NMR (CDCl 3 ) δ: 8.13-8.12 (1H, m), 8.08-8.06 (1H, m), 7.63-7.60 (1H, m), 7.56-7.52 (1H, m) , 4.74 (1H, t), 4.45 (2H, d), 2.43-2.37 (1H, m), 1.21-1.16 (2H, m), 1.00-0.95 (2H, m).

式(1g)

Figure 2019089711
で示される化合物において、R11及びR12の組合わせが[表7]に記載のいずれかの組合せである化合物。
[表7]
Figure 2019089711
本発明化合物7:1H-NMR (CDCl3) δ: 8.17-8.15 (2H, m), 7.59-7.58 (2H, m), 4.34 (2H, s), 4.08 (1H, d), 2.75 (3H, d).
本発明化合物8:1H-NMR (CDCl3) δ: 8.16-8.14 (2H, m), 7.59-7.57 (2H, m), 4.32 (2H, s), 4.06 (1H, t), 3.12-3.05 (2H, m), 1.16 (3H, t).
本発明化合物9:1H-NMR (CDCl3) δ: 8.17-8.14 (2H, m), 7.59-7.56 (2H, m), 4.33 (2H, s), 4.11 (1H, t), 3.00 (2H, td), 1.58-1.49 (2H, m), 0.91 (3H, t).
本発明化合物10:1H-NMR (CDCl3) δ: 8.17-8.14 (2H, m), 7.60-7.57 (2H, m), 4.34 (2H, s), 4.25 (1H, t), 2.89 (2H, dd), 1.02-0.94 (1H, m), 0.58-0.52 (2H, m), 0.21-0.17 (2H, m).
本発明化合物11:1H-NMR (CDCl3) δ: 8.17-8.14 (2H, m), 7.60-7.57 (2H, m), 4.29 (2H, s), 2.79 (6H, s).
本発明化合物12:1H-NMR (CDCl3) δ: 8.16-8.13 (2H, m), 7.59-7.57 (2H, m), 4.32 (2H, s), 3.23-3.20 (4H, m), 1.87-1.84 (4H, m). Formula (1g)
Figure 2019089711
In the compounds shown by, the combination of R 11 and R 12 is any combination described in [Table 7].
[Table 7]
Figure 2019089711
The present compound 7: 1 H-NMR (CDCl 3 ) δ: 8.17-8.15 (2H, m), 7.59-7.58 (2H, m), 4.34 (2H, s), 4.08 (1H, d), 2.75 (3H) , d).
The present compound 8: 1 H-NMR (CDCl 3 ) δ: 8.16-8.14 (2H, m), 7.59-7.57 (2H, m), 4.32 (2H, s), 4.06 (1H, t), 3.12-3.05 (2H, m), 1.16 (3H, t).
The present compound 9: 1 H-NMR (CDCl 3 ) δ: 8.17-8.14 (2H, m), 7.59-7.56 (2H, m), 4.33 (2H, s), 4.11 (1H, t), 3.00 (2H , td), 1.58-1.49 (2H, m), 0.91 (3H, t).
The present compound 10: 1 H-NMR (CDCl 3 ) δ: 8.17-8.14 (2H, m), 7.60-7.57 (2H, m), 4.34 (2H, s), 4.25 (1H, t), 2.89 (2H) , dd), 1.02-0.94 (1 H, m), 0.58-0.52 (2 H, m), 0.21-0.17 (2 H, m).
Invention compound 11: 1 H-NMR (CDCl 3 ) δ: 8.17-8.14 (2H, m), 7.60-7.57 (2H, m), 4.29 (2H, s), 2.79 (6H, s).
The present compound 12: 1 H-NMR (CDCl 3 ) δ: 8.16-8.13 (2H, m), 7.59-7.57 (2H, m), 4.32 (2H, s), 3.23-3.20 (4H, m), 1.87 -1.84 (4H, m).

Figure 2019089711
本発明化合物47:1H-NMR (CDCl3) δ: 8.08-8.06 (2H, m), 7.09-7.06 (2H, m), 5.22 (2H, s), 2.28 (3H, s).
Figure 2019089711
Invention compound 47: 1 H-NMR (CDCl 3 ) δ: 8.08-8.06 (2H, m), 7.09-7.06 (2H, m), 5.22 (2H, s), 2.28 (3H, s).

Figure 2019089711
本発明化合物50:1H-NMR (CDCl3) δ: 8.83 (1H, d), 8.27-8.25 (1H, m), 8.08 (1H, dd), 4.37 (2H, s), 2.91 (3H, s).
Figure 2019089711
The present compound 50: 1 H-NMR (CDCl 3 ) δ: 8.83 (1 H, d), 8. 27-8. 25 (1 H, m), 8.08 (1 H, dd), 4. 37 (2 H, s), 2. 91 (3 H, s) ).

Figure 2019089711
本発明化合物51:1H-NMR (CDCl3) δ: 8.13-8.10 (2H, m), 7.54-7.52 (2H, m), 4.26 (2H, s), 3.26-3.22 (2H, m), 3.16 (2H, t), 2.40-2.33 (2H, m).
Figure 2019089711
Invention compound 51: 1 H-NMR (CDCl 3 ) δ: 8.13-8.10 (2H, m), 7.54-7.52 (2H, m), 4.26 (2H, s), 3.26-3.22 (2H, m), 3.16 (2H, t), 2.40-2.33 (2H, m).


Figure 2019089711
本発明化合物52:1H-NMR (CDCl3) δ: 8.12-8.09 (2H, m), 7.53-7.51 (2H, m), 4.39 (2H, s), 3.28-3.25 (2H, m), 3.15-3.12 (2H, m), 2.28-2.22 (2H, m), 1.70-1.64 (2H, m).
Figure 2019089711
Invention compound 52: 1 H-NMR (CDCl 3 ) δ: 8.12-8.09 (2H, m), 7.53-7.51 (2H, m), 4.39 (2H, s), 3.28-3.25 (2H, m), 3.15 -3.12 (2H, m), 2.28-2.22 (2H, m), 1.70-1.64 (2H, m).

Figure 2019089711
本発明化合物53:1H-NMR (CDCl3) δ: 8.06-8.03 (2H, m), 7.91-7.87 (2H, m), 7.39-7.37 (2H, m), 7.22-7.17 (2H, m), 4.84 (1H, t), 4.25 (2H, d).
Figure 2019089711
The present compound 53: 1 H-NMR (CDCl 3 ) δ: 8.06-8.03 (2H, m), 7.91-7.87 (2H, m), 7.39-7.37 (2H, m), 7.22-7.17 (2H, m) , 4.84 (1H, t), 4.25 (2H, d).

Figure 2019089711
本発明化合物54:1H-NMR (CDCl3) δ: 7.98 (1H, dd), 7.89 (1H, dd), 7.71 (1H, t), 4.36 (2H, s), 2.80 (6H, s).
Figure 2019089711
Invention compound 54: 1 H-NMR (CDCl 3 ) δ: 7.98 (1H, dd), 7.89 (1H, dd), 7.71 (1H, t), 4.36 (2H, s), 2.80 (6H, s).

Figure 2019089711
本発明化合物55:1H-NMR (DMSO-D6) δ: 8.07-8.05 (2H, m), 7.84 (1H, t), 7.60-7.58 (2H, m), 4.23 (2H, d), 2.65 (6H, s).
Figure 2019089711
The present compound 55: 1 H-NMR (DMSO-D 6 ) δ: 8.07-8.05 (2H, m), 7.84 (1H, t), 7.60-7.58 (2H, m), 4.23 (2H, d), 2.65 (6H, s).

製造例2−1
0℃で、製造例1−1に記載の本発明化合物1を2.4g及びクロロホルム70mLの混合物に、m−クロロ過安息香酸2.2gを加えた。得られた混合物を室温で4時間撹拌した後、水70mLを加え、クロロホルムで抽出し、有機層を飽和亜硫酸水素ナトリウム水溶液で洗浄した。有機層を乾燥、減圧濃縮し、得られた残渣をシリカゲルカラムクロマトグラフィー(ヘキサン:酢酸エチル=1:2)に付し、下記で示される本発明化合物13を1.7g得た。

Figure 2019089711
本発明化合物13:1H-NMR (CDCl3) δ: 8.16-8.15 (2H, m), 7.49-7.47 (2H, m), 4.04 (2H, s), 2.51 (3H, s). Production Example 2-1
At 0 ° C., 2.2 g of m-chloroperbenzoic acid was added to a mixture of 2.4 g of the present compound 1 described in Production Example 1-1 and 70 mL of chloroform. The resulting mixture was stirred at room temperature for 4 hours, 70 mL of water was added, extraction was performed with chloroform, and the organic layer was washed with saturated aqueous sodium bisulfite solution. The organic layer was dried and concentrated under reduced pressure, and the obtained residue was subjected to silica gel column chromatography (hexane: ethyl acetate = 1: 2) to obtain 1.7 g of the present compound 13 shown below.
Figure 2019089711
Invention compound 13: 1 H-NMR (CDCl 3 ) δ: 8.16-8.15 (2H, m), 7.49-7.47 (2H, m), 4.04 (2H, s), 2.51 (3H, s).

製造例3−1
室温で、製造例1−1に記載の本発明化合物1を1.9g、シアナミド0.4g及びアセトニトリル20mLの混合物に、ヨードベンゼンジアセテート2.4gを加えた。得られた混合物を室温で7時間撹拌した後、減圧濃縮した。得られた残渣をシリカゲルカラムクロマトグラフィー(ヘキサン:酢酸エチル=1:2)に付し、下記で示される本発明化合物14を1.5g得た。

Figure 2019089711
本発明化合物14:1H-NMR (CDCl3) δ: 8.21-8.20 (2H, m), 7.57-7.55 (2H, m), 4.48 (1H, d), 4.25 (1H, d), 2.82 (3H, s). Production Example 3-1
To a mixture of 1.9 g of the present compound 1 described in Production Example 1-1, 0.4 g of cyanamide and 20 mL of acetonitrile at room temperature, 2.4 g of iodobenzene diacetate was added. The resulting mixture was stirred at room temperature for 7 hours and then concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography (hexane: ethyl acetate = 1: 2) to obtain 1.5 g of the present compound 14 shown below.
Figure 2019089711
The present compound 14: 1 H-NMR (CDCl 3 ) δ: 8.21-8.20 (2H, m), 7.57-7.55 (2H, m), 4.48 (1H, d), 4.25 (1H, d), 2.82 (3H) , s).

製造例3−2
製造例3−1に記載の方法に準じて製造した本発明化合物と、その物性値を以下に示す。
式(1i)

Figure 2019089711
で示される化合物において、R8、R9及びR10の組合わせが[表9]に記載の組合せである化合物。
[表9]
Figure 2019089711
本発明化合物29:1H-NMR (CDCl3) δ: 8.21-8.19 (2H, m), 7.57-7.55 (2H, m), 4.43 (1H, d), 4.21 (1H, d), 3.22-3.18 (1H, m), 2.97-2.92 (1H, m), 1.49 (3H, t).
本発明化合物56:1H-NMR (CDCl3) δ: 8.20-8.18 (2H, m), 7.60-7.58 (2H, m), 4.33 (1H, d), 4.19 (1H, d), 3.37-3.30 (1H, m), 1.55 (3H, d), 1.50 (3H, d). Production Example 3-2
The compound of the present invention produced according to the method described in Production Example 3-1 and the physical property values thereof are shown below.
Formula (1i)
Figure 2019089711
In the compounds shown by, the combination of R 8 , R 9 and R 10 is a combination described in [Table 9].
[Table 9]
Figure 2019089711
The present compound 29: 1 H-NMR (CDCl 3 ) δ: 8.21-8.19 (2H, m), 7.57-7.55 (2H, m), 4.43 (1H, d), 4.21 (1H, d), 3.22-3.18 (1H, m), 2.97-2.92 (1H, m), 1.49 (3H, t).
Invention compound 56: 1 H-NMR (CDCl 3 ) δ: 8.20-8.18 (2H, m), 7.60-7.58 (2H, m), 4.33 (1 H, d), 4.19 (1 H, d), 3.37-3.30 (1H, m), 1.55 (3H, d), 1.50 (3H, d).

式(1j)

Figure 2019089711
で示される化合物において、R8、R9及びR10の組合わせが[表10]に記載の組合せである化合物。
[表10]
Figure 2019089711
本発明化合物15:1H-NMR (CDCl3) δ: 8.22-8.19 (1H, m), 8.13 (1H, br s), 7.65-7.63 (2H, m), 4.48 (1H, d), 4.29 (1H, d), 2.84 (3H, s). Formula (1 j)
Figure 2019089711
In the compounds shown by, the combination of R 8 , R 9 and R 10 is a combination described in [Table 10].
[Table 10]
Figure 2019089711
The present compound 15: 1 H-NMR (CDCl 3 ) δ: 8.22-8.19 (1H, m), 8.13 (1H, br s), 7.65-7.63 (2H, m), 4.48 (1H, d), 4.29 (4H) 1H, d), 2.84 (3H, s).

製造例4−1
室温で、製造例3−1に記載の本発明化合物14を1.3g、塩化ルテニウム(III)水和物0.09g、アセトニトリル7mL、クロロホルム7mL及び水7mLの混合物に、過ヨウ素酸ナトリウム2.7gを加えた。得られた混合物を室温で2時間撹拌した後、水20mLを加えた。得られた混合物を濾過し、濾液を酢酸エチルで抽出し、有機層を飽和亜硫酸水素ナトリウム水溶液及び飽和食塩水で洗浄し、有機層を乾燥、減圧濃縮した。得られた残渣をシリカゲルカラムクロマトグラフィー(ヘキサン:酢酸エチル=1:2)に付し、下記で示される本発明化合物16を0.8g得た。

Figure 2019089711
本発明化合物16:1H-NMR (CDCl3) δ: 8.26-8.23 (2H, m), 7.66-7.63 (2H, m), 4.71 (2H, dd), 3.10 (3H, s). Production Example 4-1
Sodium periodate was added to a mixture of 1.3 g of the compound 14 of the present invention described in Preparation Example 3-1, 0.09 g of ruthenium (III) chloride hydrate, 7 mL of acetonitrile, 7 mL of chloroform and 7 mL of water at room temperature. Added 7g. The resulting mixture was stirred at room temperature for 2 hours and then 20 mL of water was added. The resulting mixture was filtered, the filtrate was extracted with ethyl acetate, the organic layer was washed with saturated aqueous sodium hydrogen sulfite solution and saturated brine, and the organic layer was dried and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography (hexane: ethyl acetate = 1: 2) to obtain 0.8 g of the present compound 16 shown below.
Figure 2019089711
Present compound 16: 1 H-NMR (CDCl 3 ) δ: 8.26-8.23 (2H, m), 7.66-7.63 (2H, m), 4.71 (2H, dd), 3.10 (3H, s).

製造例4−2
製造例4−1に記載の方法に準じて製造した本発明化合物と、その物性値を以下に示す。
式(1k)

Figure 2019089711
で示される化合物において、R8、R9及びR10の組合わせが[表11]に記載の組合せである化合物。
[表11]
Figure 2019089711
本発明化合物30:1H-NMR (CDCl3) δ: 8.25-8.22 (2H, m), 7.65-7.63 (2H, m), 4.70-4.62 (2H, m), 3.25-3.14 (2H, m), 1.50 (3H, t).
本発明化合物57:1H-NMR (CDCl3) δ: 8.24-8.21 (2H, m), 7.65-7.63 (2H, m), 4.68-4.59 (2H, m), 3.38-3.31 (1H, m), 1.54 (3H, d), 1.52 (3H, d). Production Example 4-2
The compound of the present invention produced according to the method described in Production Example 4-1 and the physical property values thereof are shown below.
Formula (1k)
Figure 2019089711
In the compounds shown by, the combination of R 8 , R 9 and R 10 is a combination described in [Table 11].
[Table 11]
Figure 2019089711
The present compound 30: 1 H-NMR (CDCl 3 ) δ: 8.25-8.22 (2H, m), 7.65-7.63 (2H, m), 4.74-4.62 (2H, m), 3.25-3. 14 (2H, m) , 1.5 (3H, t).
The present compound 57: 1 H-NMR (CDCl 3 ) δ: 8.24-8.21 (2H, m), 7.65-7.63 (2H, m), 4.68-4.59 (2H, m), 3.38-3.31 (1H, m) , 1.54 (3H, d), 1.52 (3H, d).

式(1l)

Figure 2019089711
で示される化合物において、R8、R9及びR10の組合わせが[表12]に記載の組合せである化合物。
[表12]
Figure 2019089711
本発明化合物17:1H-NMR (CDCl3) δ: 8.27 (1H, dt), 8.19 (1H, t), 7.73-7.71 (1H, m), 7.72-7.69 (1H, m), 4.70 (2H, dd), 3.12 (3H, s). Formula (1 l)
Figure 2019089711
In the compounds shown by, the combination of R 8 , R 9 and R 10 is a combination described in [Table 12].
[Table 12]
Figure 2019089711
The present compound 17: 1 H-NMR (CDCl 3 ) δ: 8.27 (1H, dt), 8.19 (1H, t), 7.73-7.71 (1H, m), 7.72-7.69 (1H, m), 4.70 (2H , dd), 3.12 (3H, s).

製造例5−1
室温で、製造例2−1に記載の本発明化合物13を0.5g、カルバミン酸アンモニウム0.5g及びヨードベンゼンジアセテート1.7gの混合物に、メタノール4mLを加えた。得られた混合物を室温で5時間撹拌し後、得られた混合物を減圧濃縮し、得られた残渣をシリカゲルカラムクロマトグラフィー(ヘキサン:酢酸エチル=1:2)に付し、下記で示される本発明化合物18を0.3g得た。

Figure 2019089711
本発明化合物18:1H-NMR (CDCl3) δ: 8.20-8.17 (2H, m), 7.61-7.58 (2H, m), 4.46 (1H, d), 4.32 (1H, d), 2.98 (3H, s), 2.67 (1H, br s). Production Example 5-1
To a mixture of 0.5 g of the compound 13 of the present invention described in Production Example 2-1, 0.5 g of ammonium carbamate and 1.7 g of iodobenzene diacetate at room temperature, 4 mL of methanol was added. The resulting mixture is stirred at room temperature for 5 hours, and the resulting mixture is concentrated under reduced pressure, and the resulting residue is subjected to silica gel column chromatography (hexane: ethyl acetate = 1: 2) to give the compound shown below 0.3 g of the inventive compound 18 was obtained.
Figure 2019089711
The present compound 18: 1 H-NMR (CDCl 3 ) δ: 8.20-8.17 (2H, m), 7.61-7.58 (2H, m), 4.46 (1H, d), 4.32 (1H, d), 2.98 (3H) , s), 2.67 (1H, br s).

製造例6−1
室温で、製造例1−2に記載の本発明化合物19を0.5g、アセトニトリル0.4mL、クロロホルム0.4mL、及び水0.4mLの混合物に、塩化ルテニウム(III)水和物0.04gを加えた後、過ヨウ素酸ナトリウム1.1gを加えた。得られた混合物を室温で5時間撹拌した後、濾過し、濾液を酢酸エチルで抽出し、有機層を飽和亜硫酸水素ナトリウム水溶液および飽和食塩水で洗浄し、有機層を乾燥、減圧濃縮した。得られた残渣をシリカゲルカラムクロマトグラフィー(ヘキサン:酢酸エチル=1:1)に付し、下記で示される本発明化合物20を0.35g得た。

Figure 2019089711
本発明化合物20:1H-NMR (CDCl3) δ: 8.19-8.16 (2H, m), 7.61-7.58 (2H, m), 4.30 (2H, s), 2.93 (2H, q), 1.40 (3H, t). Production Example 6-1
In a mixture of 0.5 g of the compound of the present invention 19 described in Preparation Example 1-2, 0.4 mL of acetonitrile, 0.4 mL of chloroform, and 0.4 mL of water at room temperature, 0.04 g of ruthenium (III) chloride hydrate Was added followed by 1.1 g of sodium periodate. The resulting mixture was stirred at room temperature for 5 hours, filtered, the filtrate was extracted with ethyl acetate, the organic layer was washed with saturated aqueous sodium hydrogen sulfite solution and saturated brine, and the organic layer was dried and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography (hexane: ethyl acetate = 1: 1) to obtain 0.35 g of the present compound 20 shown below.
Figure 2019089711
The present compound 20: 1 H-NMR (CDCl 3 ) δ: 8.19-8.16 (2H, m), 7.61-7.58 (2H, m), 4.30 (2H, s), 2.93 (2H, q), 1.40 (3H) , t).

製造例6−2
製造例6−1に記載の方法に準じて製造した本発明化合物と、その物性値を以下に示す。
式(1c)

Figure 2019089711
で示される化合物において、R8、R9、R10、R21及びR22の組合せが[表13]に記載の組合せである化合物。
[表13]
Figure 2019089711
本発明化合物58:1H-NMR (CDCl3) δ: 8.18-8.15 (2H, m), 7.62-7.59 (2H, m), 4.29 (2H, s), 3.09-3.02 (1H, m), 1.42 (6H, d).
本発明化合物59:1H-NMR (CDCl3) δ: 8.23-8.20 (2H, m), 7.62-7.60 (2H, m), 4.56 (2H, s). Production Example 6-2
The compound of the present invention manufactured according to the method described in Production Example 6-1 and the physical property values thereof are shown below.
Formula (1c)
Figure 2019089711
In the compounds shown by, the combination of R 8 , R 9 , R 10 , R 21 and R 22 is a combination described in [Table 13].
[Table 13]
Figure 2019089711
The present compound 58: 1 H-NMR (CDCl 3 ) δ: 8.18-8.15 (2H, m), 7.62-7.59 (2H, m), 4.29 (2H, s), 3.09-3.02 (1H, m), 1.42 (6H, d).
Invention compound 59: 1 H-NMR (CDCl 3 ) δ: 8.23-8.20 (2H, m), 7.62-7.60 (2H, m), 4.56 (2H, s).

式(1m)

Figure 2019089711
で示される化合物において、mが[表14]に記載のいずれかである化合物。
[表14]
Figure 2019089711
本発明化合物60:1H-NMR (CDCl3) δ: 8.14-8.10 (2H, m), 7.21-7.18 (2H, m), 5.05 (2H, s), 3.06 (3H, s).
本発明化合物61:1H-NMR (CDCl3) δ: 8.10-8.08 (2H, m), 7.05-7.03 (2H, m), 4.53 (2H, t), 3.50 (2H, t), 3.09 (3H, s).
本発明化合物62:1H-NMR (CDCl3) δ: 8.08-8.05 (2H, m), 7.03-7.00 (2H, m), 4.21 (2H, t), 3.28 (2H, t), 2.98 (3H, s), 2.44-2.37 (2H, m). Formula (1 m)
Figure 2019089711
In the compound shown by these, compounds in which m is any of those listed in [Table 14].
[Table 14]
Figure 2019089711
Invention compound 60: 1 H-NMR (CDCl 3 ) δ: 8.14-8.10 (2H, m), 7.21-7.18 (2H, m), 5.05 (2H, s), 3.06 (3H, s).
The present compound 61: 1 H-NMR (CDCl 3 ) δ: 8.10-8.08 (2H, m), 7.05-7.03 (2H, m), 4.53 (2H, t), 3.50 (2H, t), 3.09 (3H , s).
The present compound 62: 1 H-NMR (CDCl 3 ) δ: 8.08-8.05 (2H, m), 7.03-7.00 (2H, m), 4.21 (2H, t), 3.28 (2H, t), 2.98 (3H) , s), 2.44-2.37 (2H, m).

製造例7−1
0℃で、4−[5−(トリフルオロメチル)−1,2,4−オキサジアゾール−3−イル]フェノール1.0g、2−(メチルチオ)エタノール0.8g及びテトラヒドロフラン30mLの混合物に、トリフェニルホスフィン2.0g及びビス(2−メトキシエチル)ジアゼン−1,2−ジカルボキシレートを順に加えた後、45℃に昇温し3時間撹拌した。反応混合物を室温まで冷却し、減圧濃縮した後、水20mLを加えた。酢酸エチルで抽出し、有機層を飽和食塩水で洗浄し、有機層を乾燥、減圧濃縮した。得られた残渣をシリカゲルカラムクロマトグラフィー(ヘキサン:酢酸エチル=4:1)に付し、下記で示される本発明化合物48を0.69g得た。

Figure 2019089711
本発明化合物48:1H-NMR (CDCl3) δ: 8.07-8.04 (2H, m), 7.03-7.01 (2H, m), 4.24 (2H, t), 2.92 (2H, t), 2.24 (3H, s). Production Example 7-1
In a mixture of 1.0 g of 4- [5- (trifluoromethyl) -1,2,4-oxadiazol-3-yl] phenol, 0.8 g of 2- (methylthio) ethanol and 30 mL of tetrahydrofuran at 0 ° C. After 2.0 g of triphenylphosphine and bis (2-methoxyethyl) diazene-1,2-dicarboxylate were sequentially added, the temperature was raised to 45 ° C. and stirring was performed for 3 hours. The reaction mixture was cooled to room temperature and concentrated under reduced pressure, and then 20 mL of water was added. The mixture was extracted with ethyl acetate, the organic layer was washed with brine, and the organic layer was dried and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography (hexane: ethyl acetate = 4: 1) to obtain 0.69 g of the present compound 48 shown below.
Figure 2019089711
Invention compound 48: 1 H-NMR (CDCl 3 ) δ: 8.07-8.04 (2H, m), 7.03-7.01 (2H, m), 4.24 (2H, t), 2. 92 (2H, t), 2.24 (3H) , s).

製造例7−2
製造例7−1に記載の方法に準じて、本発明化合物49を製造した。

Figure 2019089711
本発明化合物49:1H-NMR (CDCl3) δ: 8.06-8.03 (2H, m), 7.03-7.00 (2H, m), 4.15 (2H, t), 2.71 (2H, t), 2.15-2.08 (5H, m). Production Example 7-2
The present compound 49 was produced according to the method described in Production Example 7-1.
Figure 2019089711
The present compound 49: 1 H-NMR (CDCl 3 ) δ: 8.06-8.03 (2H, m), 7.03-7.00 (2H, m), 4.15 (2H, t), 2.71 (2H, t), 2.15-2.08 (5H, m).

製造例8−1
0℃で、製造例1−2に記載の本発明化合物5を0.4g、及びN,N−ジメチルホルムアミド20mLの混合物に、水素化ナトリウム(60%、油性)0.06gを加えた後、室温で10分間撹拌した。得られた混合物に、0℃で、ヨウ化メチル0.3gを加えた後、室温で5時間撹拌した。得られた混合物に水50mLを加え、酢酸エチルで抽出した。有機層を飽和食塩水で洗浄し、乾燥、減圧濃縮し、得られた残渣をシリカゲルカラムクロマトグラフィー(ヘキサン:酢酸エチル=1:1)に付し、本発明化合物31を0.3g得た。

Figure 2019089711
本発明化合物31:1H-NMR (CDCl3) δ: 8.14-8.12 (2H, m), 7.54-7.52 (2H, m), 4.40 (2H, s), 2.90 (3H, s), 2.82 (3H, s). Production Example 8-1
After adding 0.06 g of sodium hydride (60%, oily) to a mixture of 0.4 g of the compound 5 of the present invention described in Preparation Example 1-2 and 20 mL of N, N-dimethylformamide at 0 ° C. Stir at room temperature for 10 minutes. After 0.3 g of methyl iodide was added to the obtained mixture at 0 ° C., the mixture was stirred at room temperature for 5 hours. To the resulting mixture was added 50 mL of water and extracted with ethyl acetate. The organic layer was washed with saturated brine, dried and concentrated under reduced pressure, and the obtained residue was subjected to silica gel column chromatography (hexane: ethyl acetate = 1: 1) to obtain 0.3 g of the present compound 31.
Figure 2019089711
The present compound 31: 1 H-NMR (CDCl 3 ) δ: 8.14-8.12 (2H, m), 7.54-7.52 (2H, m), 4.40 (2H, s), 2.90 (3H, s), 2.82 (3H) , s).

製造例8−2
製造例8−1に記載の方法に準じて製造した本発明化合物と、その物性値を以下に示す。
Production Example 8-2
The compound of the present invention produced according to the method described in Production Example 8-1 and the physical properties thereof are shown below.

式(1e)

Figure 2019089711
で示される化合物において、R6、R8、R9及びR10の組合せが[表16]に記載のいずれかの組合せである化合物。
[表16]
Figure 2019089711
本発明化合物63:1H-NMR (CDCl3) δ: 8.13-8.10 (2H, m), 7.56-7.53 (2H, m), 4.47 (2H, s), 3.31 (2H, q), 2.91 (3H, s), 1.15 (3H, t).
本発明化合物64:1H-NMR (CDCl3) δ: 8.11-8.08 (2H, m), 7.60-7.57 (2H, m), 4.44 (2H, s), 4.22-4.16 (1H, m), 2.88 (3H, s), 1.19 (6H, d).
本発明化合物65:1H-NMR (CDCl3) δ: 8.13-8.10 (2H, m), 7.56-7.54 (2H, m), 4.46 (2H, s), 3.01 (2H, d), 2.86 (3H, s), 1.84-1.74 (1H, m), 0.87 (6H, d).
本発明化合物66:1H-NMR (CDCl3) δ: 8.14-8.12 (2H, m), 7.58-7.56 (2H, m), 4.53 (2H, s), 3.96 (2H, d), 3.05 (3H, s), 2.45 (1H, t).
本発明化合物67:1H-NMR (CDCl3) δ: 8.14 (2H, d), 7.54 (2H, d), 6.06-5.78 (1H, m), 4.62 (2H, s), 3.57 (2H, td), 3.01 (3H, s).
本発明化合物68:1H-NMR (CDCl3) δ: 8.12-8.10 (2H, m), 7.56 (2H, d), 4.58 (2H, s), 3.12 (2H, d), 2.98 (3H, s), 0.94-0.88 (1H, m), 0.54-0.49 (2H, m), 0.20-0.16 (2H, m).
本発明化合物69:1H-NMR (CDCl3) δ: 8.18-8.16 (2H, m), 7.58-7.56 (2H, m), 4.55 (2H, s), 4.09 (2H, s), 3.11 (3H, s).
本発明化合物70:1H-NMR (CDCl3) δ: 8.10-8.08 (2H, m), 7.47-7.45 (2H, m), 7.36-7.32 (3H, m), 7.30-7.28 (2H, m), 4.43 (2H, s), 4.38 (2H, s), 2.85 (3H, s).
本発明化合物71:1H-NMR (CDCl3) δ: 8.13-8.11 (2H, m), 7.55 (2H, d), 4.57 (2H, s), 4.56 (2H, s), 3.47 (2H, q), 3.01 (3H, s), 1.20 (3H, t).
本発明化合物72:1H-NMR (CDCl3) δ: 8.14-8.11 (2H, m), 7.54-7.52 (2H, m), 4.45 (2H, s), 3.09 (2H, q), 2.83 (3H, s), 1.42 (3H, t).
本発明化合物73:1H-NMR (CDCl3) δ: 8.13-8.10 (2H, m), 7.55-7.53 (2H, m), 4.51 (2H, s), 3.31 (2H, q), 3.05 (2H, q), 1.40 (3H, t), 1.13 (3H, t).
本発明化合物74:1H-NMR (CDCl3) δ: 8.11-8.07 (2H, m), 7.60-7.57 (2H, m), 4.46 (2H, s), 4.18-4.11 (1H, m), 2.93 (2H, q), 1.35 (3H, t), 1.19 (6H, d).
本発明化合物75:1H-NMR (CDCl3) δ: 8.14-8.10 (2H, m), 7.53 (2H, d), 4.48 (2H, s), 3.36-3.29 (1H, m), 2.84 (3H, s), 1.42 (6H, d).
本発明化合物76:1H-NMR (CDCl3) δ: 8.12-8.09 (2H, m), 7.55 (2H, d), 4.53 (2H, s), 3.30 (2H, q), 3.24-3.17 (1H, m), 1.40 (6H, d), 1.12 (3H, t).
本発明化合物77:1H-NMR (CDCl3) δ: 8.10-8.07 (2H, m), 7.59 (2H, d), 4.47 (2H, s), 4.15-4.08 (1H, m), 3.03-2.96 (1H, m), 1.34 (6H, d), 1.17 (6H, d). Formula (1e)
Figure 2019089711
In the compounds shown by, the combination of R 6 , R 8 , R 9 and R 10 is any combination described in [Table 16].
[Table 16]
Figure 2019089711
The present compound 63: 1 H-NMR (CDCl 3 ) δ: 8.13-8.10 (2H, m), 7.56-7.53 (2H, m), 4.47 (2H, s), 3.31 (2H, q), 2.91 (3H) , s), 1.15 (3H, t).
Invention compound 64: 1 H-NMR (CDCl 3 ) δ: 8.11-8.08 (2H, m), 7.60-7.57 (2H, m), 4.44 (2H, s), 4.22-4.16 (1H, m), 2.88 (3H, s), 1.19 (6H, d).
The present compound 65: 1 H-NMR (CDCl 3 ) δ: 8.13-8.10 (2H, m), 7.56-7.54 (2H, m), 4.46 (2H, s), 3.01 (2H, d), 2.86 (3H) , s), 1.84-1.74 (1 H, m), 0.87 (6 H, d).
The present compound 66: 1 H-NMR (CDCl 3 ) δ: 8.14-8.12 (2H, m), 7.58-7.56 (2H, m), 4.53 (2H, s), 3.96 (2H, d), 3.05 (3H , s), 2.45 (1 H, t).
The present compound 67: 1 H-NMR (CDCl 3 ) δ: 8.14 (2H, d), 7.54 (2H, d), 6.06-5.78 (1H, m), 4.62 (2H, s), 3.57 (2H, td ), 3.01 (3H, s).
Invention compound 68: 1 H-NMR (CDCl 3 ) δ: 8.12-8.10 (2H, m), 7.56 (2H, d), 4.58 (2H, s), 3.12 (2H, d), 2.98 (3H, s) ), 0.94-0.88 (1 H, m), 0.54-0.49 (2 H, m), 0.20-0.16 (2 H, m).
The present compound 69: 1 H-NMR (CDCl 3 ) δ: 8.18-8.16 (2H, m), 7.58-7.56 (2H, m), 4.55 (2H, s), 4.09 (2H, s), 3.11 (3H , s).
The present compound 70: 1 H-NMR (CDCl 3 ) δ: 8.10-8.08 (2H, m), 7.47-7.45 (2H, m), 7.36-7.32 (3H, m), 7.30-7. 28 (2H, m) , 4.43 (2H, s), 4.38 (2H, s), 2.85 (3H, s).
The present compound 71: 1 H-NMR (CDCl 3 ) δ: 8.13-8.11 (2H, m), 7.55 (2H, d), 4.57 (2H, s), 4.56 (2H, s), 3.47 (2H, q) ), 3.01 (3H, s), 1.20 (3H, t).
The present compound 72: 1 H-NMR (CDCl 3 ) δ: 8.14-8.11 (2H, m), 7.54-7.52 (2H, m), 4.45 (2H, s), 3.09 (2H, q), 2.83 (3H , s), 1.42 (3H, t).
Invention compound 73: 1 H-NMR (CDCl 3 ) δ: 8.13-8.10 (2H, m), 7.55 to 7.53 (2H, m), 4.51 (2H, s), 3.31 (2H, q), 3.05 (2H , q), 1.40 (3H, t), 1.13 (3H, t).
The present compound 74: 1 H-NMR (CDCl 3 ) δ: 8.11 to 8.07 (2H, m), 7.60 to 7.57 (2H, m), 4.46 (2H, s), 4.18 to 4.11 (1H, m), 2.93 (2H, q), 1.35 (3H, t), 1.19 (6H, d).
The present compound 75: 1 H-NMR (CDCl 3 ) δ: 8.14-8.10 (2H, m), 7.53 (2H, d), 4.48 (2H, s), 3.36-3.29 (1H, m), 2.84 (3H) , s), 1.42 (6H, d).
The present compound 76: 1 H-NMR (CDCl 3 ) δ: 8.12-8.09 (2H, m), 7.55 (2H, d), 4.53 (2H, s), 3.30 (2H, q), 3.24-3.17 (1H , m), 1.40 (6H, d), 1.12 (3H, t).
Invention compound 77: 1 H-NMR (CDCl 3 ) δ: 8.10-8.07 (2H, m), 7.59 (2H, d), 4.47 (2H, s), 4.15-4.08 (1H, m), 3.03-2.96 (1H, m), 1.34 (6H, d), 1.17 (6H, d).

式(1o)で示される化合物において、R6、R8、R9及びR10の組合せが[表17]に記載のいずれかの組合せである化合物。

Figure 2019089711
[表17]
Figure 2019089711
本発明化合物32:1H-NMR (CDCl3) δ: 8.10-8.07 (2H, m), 7.65-7.63 (1H, m), 7.58-7.54 (1H, m), 4.40 (2H, s), 2.90 (3H, s), 2.81 (3H, s).
本発明化合物78:1H-NMR (CDCl3) δ: 8.09-8.06 (2H, m), 7.68-7.65 (1H, m), 7.57-7.53 (1H, m), 4.48 (2H, s), 3.30 (2H, q), 2.92 (3H, s), 1.16 (3H, t). In the compound represented by the formula (1o), compounds wherein the combination of R 6 , R 8 , R 9 and R 10 is any one of the combinations described in [Table 17].
Figure 2019089711
[Table 17]
Figure 2019089711
Invention compound 32: 1 H-NMR (CDCl 3 ) δ: 8.10-8.07 (2H, m), 7.65-7.63 (1H, m), 7.58-7.54 (1H, m), 4.40 (2H, s), 2.90 (3H, s), 2.81 (3H, s).
Invention compound 78: 1 H-NMR (CDCl 3 ) δ: 8.09-8.06 (2H, m), 7.68-7.65 (1H, m), 7.57-7.53 (1H, m), 4.48 (2H, s), 3.30 (2H, q), 2.92 (3H, s), 1.16 (3H, t).

式(1p)

Figure 2019089711
で示される化合物において、R6、R11及びR12の組合せが[表18]に記載のいずれかの組合せである化合物。
[表18]
Figure 2019089711
本発明化合物79:1H-NMR (CDCl3) δ: 8.13-8.10 (2H, m), 7.51 (2H, d), 4.41 (2H, s), 2.87 (6H, s), 2.75 (3H, s).
本発明化合物80:1H-NMR (CDCl3) δ: 8.12-8.10 (2H, m), 7.53 (2H, d), 4.47 (2H, s), 3.24 (2H, q), 2.82 (6H, s), 1.13 (3H, t).
本発明化合物81:1H-NMR (CDCl3) δ: 8.10-8.07 (2H, m), 7.57-7.55 (2H, m), 4.42 (2H, s), 4.07-4.01 (1H, m), 2.72 (6H, s), 1.19 (6H, d).
本発明化合物82:1H-NMR (CDCl3) δ: 8.15-8.13 (2H, m), 7.54-7.52 (2H, m), 6.11-5.81 (1H, m), 4.56 (2H, s), 3.49-3.41 (2H, m), 2.85 (6H, s).
本発明化合物83:1H-NMR (CDCl3) δ: 8.13-8.11 (2H, m), 7.56-7.54 (2H, m), 4.60 (2H, s), 3.89 (2H, d), 2.91 (6H, s), 2.40 (1H, t).
本発明化合物84:1H-NMR (CDCl3) δ: 8.11 (2H, d), 7.54 (2H, d), 4.58 (2H, s), 3.85-3.84 (2H, m), 2.89 (6H, s), 1.88 (3H, t).
本発明化合物85:1H-NMR (CDCl3) δ: 8.17-8.15 (2H, m), 7.55 (2H, d), 4.60 (2H, s), 4.00 (2H, s), 2.96 (6H, s). Formula (1p)
Figure 2019089711
In the compounds shown by, the combination of R 6 , R 11 and R 12 is any combination described in [Table 18].
[Table 18]
Figure 2019089711
Invention compound 79: 1 H-NMR (CDCl 3 ) δ: 8.13-8.10 (2H, m), 7.51 (2H, d), 4.41 (2H, s), 2.87 (6H, s), 2.75 (3H, s) ).
The present compound 80: 1 H-NMR (CDCl 3 ) δ: 8.12-8.10 (2H, m), 7.53 (2H, d), 4.47 (2H, s), 3.24 (2H, q), 2.82 (6H, s) ), 1.13 (3H, t).
Invention compound 81: 1 H-NMR (CDCl 3 ) δ: 8.10-8.07 (2H, m), 7.57-7.55 (2H, m), 4.42 (2H, s), 4.07-4.01 (1H, m), 2.72 (6H, s), 1.19 (6H, d).
Invention compound 82: 1 H-NMR (CDCl 3 ) δ: 8.15-8.13 (2H, m), 7.54-7.52 (2H, m), 6.11-5.81 (1H, m), 4.56 (2H, s), 3.49 -3.41 (2H, m), 2.85 (6H, s).
The present compound 83: 1 H-NMR (CDCl 3 ) δ: 8.13-8.11 (2H, m), 7.56-7.54 (2H, m), 4.60 (2H, s), 3.89 (2H, d), 2.91 (6H , s), 2.40 (1 H, t).
Invention compound 84: 1 H-NMR (CDCl 3 ) δ: 8.11 (2H, d), 7.54 (2H, d), 4.58 (2H, s), 3.85-3.84 (2H, m), 2.89 (6H, s) ), 1.88 (3H, t).
Invention compound 85: 1 H-NMR (CDCl 3 ) δ: 8.17-8.15 (2H, m), 7.55 (2H, d), 4.60 (2H, s), 4.00 (2H, s), 2.96 (6H, s) ).

製造例9−1
室温で、製造例5−1に記載の本発明化合物18を0.4g、及びクロロホルム10mLの混合物に、トリエチルアミン0.3mLを加えた後、プロピオニルクロライド0.12gを加え、室温で20時間撹拌した。反応混合物を減圧濃縮し、得られた残渣をシリカゲルカラムクロマトグラフィー(酢酸エチル)に付し、本発明化合物86を0.4g得た。

Figure 2019089711
本発明化合物86:1H-NMR (CDCl3) δ: 8.19-8.17 (2H, m), 7.59-7.57 (2H, m), 4.83-4.75 (2H, m), 3.08 (3H, s), 2.39 (2H, q), 1.13 (3H, t). Production Example 9-1
After 0.3 mL of triethylamine was added to a mixture of 0.4 g of the present compound 18 described in Preparation Example 5-1 and 10 mL of chloroform at room temperature, 0.12 g of propionyl chloride was added, and the mixture was stirred at room temperature for 20 hours. . The reaction mixture was concentrated under reduced pressure, and the obtained residue was subjected to silica gel column chromatography (ethyl acetate) to give 0.4 g of the present compound 86.
Figure 2019089711
Invention compound 86: 1 H-NMR (CDCl 3 ) δ: 8.19-8.17 (2H, m), 7.59-7.57 (2H, m), 4.83-4.75 (2H, m), 3.08 (3H, s), 2.39 (2H, q), 1.13 (3H, t).

製造例9−2
製造例9−1に記載の方法に準じて製造した本発明化合物と、その物性値を以下に示す。
Production Example 9-2
The compound of the present invention produced according to the method described in Production Example 9-1 and the physical properties thereof are shown below.

式(1q)

Figure 2019089711
で示される化合物において、R7が[表19]に記載のいずれかである化合物。
[表19]
Figure 2019089711
本発明化合物87:1H-NMR (CDCl3) δ: 8.19-8.16 (2H, m), 7.60-7.57 (2H, m), 4.83-4.74 (2H, m), 3.09 (3H, s), 2.59-2.52 (1H, m), 1.15 (6H, dd).
本発明化合物88:1H-NMR (CDCl3) δ: 8.24-8.21 (2H, m), 7.62-7.59 (2H, m), 4.88-4.80 (2H, m), 3.22 (3H, s). Formula (1 q)
Figure 2019089711
In the compounds shown by these, compounds in which R 7 is any of those described in [Table 19].
[Table 19]
Figure 2019089711
Invention compound 87: 1 H-NMR (CDCl 3 ) δ: 8.19-8.16 (2H, m), 7.60-7.57 (2H, m), 4.83-4.74 (2H, m), 3.09 (3H, s), 2.59 -2.52 (1 H, m), 1.15 (6 H, dd).
Invention compound 88: 1 H-NMR (CDCl 3 ) δ: 8.24-8.21 (2H, m), 7.62-7.59 (2H, m), 4.88-4.80 (2H, m), 3.22 (3H, s).

Figure 2019089711
本発明化合物89:1H-NMR (CDCl3) δ: 8.22-8.19 (2H, m), 7.63-7.60 (2H, m), 4.84-4.74 (2H, m), 3.76 (3H, s), 3.05 (3H, s).
Figure 2019089711
Invention compound 89: 1 H-NMR (CDCl 3 ) δ: 8.22-8.19 (2H, m), 7.63-7.60 (2H, m), 4.84-4.74 (2H, m), 3.76 (3H, s), 3.05 (3H, s).

次に、上記の本発明化合物を製造する際の中間体化合物の製造例を示す。 Next, production examples of the intermediate compounds in producing the above-mentioned compound of the present invention will be shown.

参考製造例1−1
参考製造例3−1に記載の中間体(A2a1)1.7g、エタノール60mL、及び50%−ヒドロキシルアミン水溶液2.2mLの混合物を加熱還流下、5時間撹拌した。室温に冷却後、反応混合物を減圧濃縮した後、水20mLを加えて、酢酸エチルで抽出した。有機層を飽和食塩水で洗浄し、乾燥、減圧濃縮した後、中間体(A1a1)を1.7g得た。

Figure 2019089711
中間体(A1a1):1H-NMR (DMSO-D6) δ: 9.60 (1H, s), 7.63-7.60 (2H, m), 7.30-7.28 (2H, m), 5.78 (2H, s), 3.69 (2H, s), 1.95 (3H, s). Reference Production Example 1-1
A mixture of 1.7 g of the intermediate (A2a1) described in Reference Production Example 3-1, 60 mL of ethanol, and 2.2 mL of a 50% -hydroxylamine aqueous solution was stirred under heating reflux for 5 hours. After cooling to room temperature, the reaction mixture was concentrated under reduced pressure, 20 mL of water was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried and concentrated under reduced pressure to obtain 1.7 g of an intermediate (A1a1).
Figure 2019089711
Intermediate (A1a1): 1 H-NMR (DMSO-D 6 ) δ: 9.60 (1H, s), 7.63-7.60 (2H, m), 7.30-7.28 (2H, m), 5.78 (2H, s), 3.69 (2H, s), 1.95 (3H, s).

参考製造例1−2
参考製造例1−1に記載の方法に準じて製造した中間体化合物と、その物性値を以下に示す。
Reference Production Example 1-2
Intermediate compounds produced according to the method described in Reference Production Example 1-1 and physical properties thereof are shown below.

式(A1a)

Figure 2019089711
で示される化合物において、R8、R9及びR10の組合わせが下表に記載のいずれかの組合せである化合物。
Figure 2019089711
中間体(A1a2):1H-NMR (CDCl3) δ: 7.59-7.56 (2H, m), 7.37-7.33 (2H, m), 4.86 (2H, s), 3.73 (2H, s), 2.43 (2H, q), 1.23 (3H, t).
中間体(A1a3):1H-NMR (CDCl3) δ: 7.58-7.56 (2H, m), 7.38-7.36 (2H, m), 4.87 (2H, s), 3.75 (2H, s), 2.81-2.75 (1H, m), 1.25 (6H, d, J = 6.9 Hz).
中間体(A1a4):1H-NMR (DMSO-D6) δ: 9.65 (1H, s), 7.65 (2H, d), 7.39 (2H, d), 5.81 (2H, s), 4.32 (2H, s). Formula (A1a)
Figure 2019089711
In the compounds shown by, the combination of R 8 , R 9 and R 10 is any combination described in the following table.
Figure 2019089711
Intermediate (A1a2): 1 H-NMR (CDCl 3 ) δ: 7.59 to 7.56 (2H, m), 7.37 to 7.33 (2H, m), 4.86 (2H, s), 3.73 (2H, s), 2.43 ( 2H, q), 1.23 (3H, t).
Intermediate (A1a3): 1 H-NMR (CDCl 3 ) δ: 7.58 to 7.56 (2H, m), 7.38 to 7.36 (2H, m), 4.87 (2H, s), 3.75 (2H, s), 2.81- 2.75 (1 H, m), 1.25 (6 H, d, J = 6.9 Hz).
Intermediate (A1a4): 1 H-NMR (DMSO-D 6 ) δ: 9.65 (1H, s), 7.65 (2H, d), 7.39 (2H, d), 5.81 (2H, s), 4.32 (2H, 2) s).

式(A1b)

Figure 2019089711
で示される化合物において、R8、R9及びR10の組合わせが下表に記載の組合せである化合物。
Figure 2019089711
中間体(A1b1):1H-NMR (CDCl3) δ: 8.25 (1H, s), 7.58-7.57 (1H, m), 7.52-7.51 (1H, m), 7.37-7.36 (2H, m), 4.90 (2H, s), 3.69 (2H, s), 1.99 (3H, s). Formula (A1 b)
Figure 2019089711
Compounds in which R 8 , R 9 and R 10 have the combinations given in the following table.
Figure 2019089711
Intermediate (A1b1): 1 H-NMR (CDCl 3 ) δ: 8.25 (1H, s), 7.58-7.57 (1H, m), 7.52-7.51 (1H, m), 7.37-7.36 (2H, m), 4.90 (2H, s), 3.69 (2H, s), 1.99 (3H, s).

式(A1e)

Figure 2019089711
で示される化合物において、R6、R8、R9及びR10の組合わせが下表に記載のいずれかの組合せである化合物。
Figure 2019089711
中間体(A1e1):1H-NMR (DMSO-D6) δ: 9.61 (1H, s), 7.66-7.64 (2H, m), 7.58 (1H, s), 7.33 (2H, d, J = 8.5 Hz), 5.80 (2H, s), 4.16 (2H, d, J = 3.9 Hz), 2.86 (3H, s).
中間体(A1e2):1H-NMR (DMSO-D6) δ: 9.61 (1H, s), 7.66-7.64 (2H, m), 7.34-7.32 (2H, m), 5.81 (2H, s), 4.14 (2H, d), 2.94 (2H, q), 1.16 (3H, t).
中間体(A1e3):1H-NMR (DMSO-D6) δ: 9.64 (1H, s), 7.65-7.58 (3H, m), 7.34-7.32 (2H, m), 5.86 (2H, s), 4.17 (2H, d), 3.08 (1H, t), 1.21 (6H, d).
中間体(A1e4):1H-NMR (DMSO-D6) δ: 9.43-9.19 (1H, m), 7.74-7.64 (3H, m), 7.36 (2H, t), 6.07 (2H, s), 4.20 (2H, d), 2.50-2.44 (1H, m), 1.02-0.97 (2H, m), 0.88-0.87 (2H, m).
中間体(A1e5):1H-NMR (DMSO-D6) δ: 9.61 (1H, s), 7.66-7.63 (2H, m), 7.33 (2H, d), 5.79 (2H, s), 4.19-4.15 (2H, m), 2.93-2.88 (2H, m), 1.68-1.59 (2H, m), 0.93-0.89 (3H, m).
中間体(A1e6):1H-NMR (DMSO-D6) δ: 9.64 (1H, s), 7.66-7.60 (3H, m), 7.35-7.32 (2H, m), 5.85 (2H, s), 4.15 (2H, d), 2.93-2.89 (2H, m), 1.62-1.54 (2H, m), 1.36-1.26 (2H, m), 0.84 (3H, t).
中間体(A1e7):1H-NMR (DMSO-D6) δ: 9.60 (1H, s), 7.66-7.59 (3H, m), 7.34-7.32 (2H, m), 5.79 (2H, s), 4.15 (2H, d), 2.83 (2H, d), 2.10-2.00 (1H, m), 0.97 (6H, d).
中間体(A1e8):1H-NMR (DMSO-D6) δ: 9.60 (1H, s), 7.68 (1H, s), 7.65-7.62 (2H, m), 7.40-7.34 (5H, m), 7.30 (2H, d), 5.79 (2H, s), 4.33 (2H, s), 4.10 (2H, s).
中間体(A1e9):1H-NMR (DMSO-D6) δ: 9.63 (1H, s), 7.66 (2H, d), 7.34 (2H, d), 5.80 (2H, s), 4.35 (2H, s), 2.95 (3H, s), 2.48-2.43 (1H, m), 0.64 (4H, d).
中間体(A1e10):1H-NMR (DMSO-D6) δ: 9.59 (1H, s), 7.56 (2H, d), 7.39-7.31 (4H, m), 7.26-7.23 (3H, m), 5.74 (2H, s), 4.87 (2H, s), 3.09 (3H, s).
中間体(A1e11):1H-NMR (DMSO-D6) δ: 9.61 (1H, s), 7.56-7.54 (2H, m), 7.48-7.46 (1H, m), 7.26-7.20 (1H, m), 7.19-7.14 (4H, m), 5.76 (2H, s), 4.88-4.85 (1H, m), 4.59-4.56 (1H, m), 3.13 (3H, s), 2.02 (3H, s).
中間体(A1e12):1H-NMR (DMSO-D6) δ: 9.59 (1H, s), 7.57-7.55 (2H, m), 7.26-7.23 (2H, m), 7.21-7.15 (3H, m), 7.07-7.05 (1H, m), 5.75 (2H, s), 4.85 (2H, s), 3.08 (3H, s), 2.26 (3H, s).
中間体(A1e13):1H-NMR (DMSO-D6) δ: 9.59 (1H, s), 7.56-7.54 (2H, m), 7.26-7.22 (4H, m), 7.13-7.11 (2H, m), 5.75 (2H, s), 4.83 (2H, s), 3.06 (3H, s), 2.24 (3H, s).
中間体(A1e14):1H-NMR (DMSO-D6) δ: 9.61 (1H, s), 7.57 (2H, d), 7.46-7.42 (1H, m), 7.36-7.30 (1H, m), 7.27-7.21 (3H, m), 7.18-7.14 (1H, m), 5.76 (2H, s), 4.80 (2H, s), 3.17 (3H, s).
中間体(A1e15):1H-NMR (DMSO-D6) δ: 9.60 (1H, s), 7.56 (2H, d), 7.29-7.23 (3H, m), 7.09-7.07 (1H, m), 7.04-7.02 (1H, m), 6.83-6.79 (1H, m), 5.76 (2H, s), 4.73 (2H, s), 3.87 (3H, s), 3.07 (3H, s).
中間体(A1e16):1H-NMR (DMSO-D6) δ: 9.58 (1H, s), 7.64-7.62 (2H, m), 7.38-7.36 (2H, m), 5.77 (2H, s), 4.48 (2H, s), 3.04 (3H, s), 1.34 (9H, s).
中間体(A1e17):1H-NMR (DMSO-D6) δ: 9.63 (1H, s), 7.68-7.66 (2H, m), 7.39-7.36 (2H, m), 5.81 (2H, s), 4.38 (2H, s), 3.29-3.25 (2H, m), 3.03 (3H, s), 2.49-2.46 (2H, m), 1.97 (3H, s). Formula (A1e)
Figure 2019089711
In the compounds shown by, a combination of R 6 , R 8 , R 9 and R 10 is any combination described in the following table.
Figure 2019089711
Intermediate (A1e1): 1 H-NMR (DMSO-D 6 ) δ: 9.61 (1H, s), 7.66-7.64 (2H, m), 7.58 (1H, s), 7.33 (2H, d, J = 8.5) Hz), 5.80 (2H, s), 4.16 (2H, d, J = 3.9 Hz), 2.86 (3H, s).
Intermediate (A1e2): 1 H-NMR (DMSO-D 6 ) δ: 9.61 (1H, s), 7.66-7.64 (2H, m), 7.34-7.32 (2H, m), 5.81 (2H, s), 4.14 (2H, d), 2.94 (2H, q), 1.16 (3H, t).
Intermediate (A1e3): 1 H-NMR (DMSO-D 6 ) δ: 9.64 (1H, s), 7.65-7.58 (3H, m), 7.34-7.32 (2H, m), 5.86 (2H, s), 4.17 (2H, d), 3.08 (1 H, t), 1.21 (6 H, d).
Intermediate (A1e4): 1 H-NMR (DMSO-D 6 ) δ: 9.43-9.19 (1H, m), 7.74-7.64 (3H, m), 7.36 (2H, t), 6.07 (2H, s), 4.20 (2H, d), 2.50-2.44 (1H, m), 1.02-0.97 (2H, m), 0.88-0.87 (2H, m).
Intermediate (A1e5): 1 H-NMR (DMSO-D 6 ) δ: 9.61 (1H, s), 7.66-7.63 (2H, m), 7.33 (2H, d), 5.79 (2H, s), 4.19- 4.15 (2H, m), 2.93-2.88 (2H, m), 1.68-1.59 (2H, m), 0.93-0.89 (3H, m).
Intermediate (A1e6): 1 H-NMR (DMSO-D 6 ) δ: 9.64 (1H, s), 7.66-7.60 (3H, m), 7.35-7. 32 (2H, m), 5.85 (2H, s), 4.15 (2H, d), 2.93-2.89 (2H, m), 1.62-1.54 (2H, m), 1.36-1.26 (2H, m), 0.84 (3H, t).
Intermediate (A1e7): 1 H-NMR (DMSO-D 6 ) δ: 9.60 (1H, s), 7.66-7.59 (3H, m), 7.34-7.32 (2H, m), 5.79 (2H, s), 4.15 (2H, d), 2.83 (2H, d), 2.10-2.00 (1 H, m), 0.97 (6 H, d).
Intermediate (A1e8): 1 H-NMR (DMSO-D 6 ) δ: 9.60 (1H, s), 7.68 (1H, s), 7.65-7.62 (2H, m), 7.40-7.34 (5H, m), 7.30 (2H, d), 5.79 (2H, s), 4.33 (2H, s), 4.10 (2H, s).
Intermediate (A1e9): 1 H-NMR (DMSO-D 6 ) δ: 9.63 (1H, s), 7.66 (2H, d), 7.34 (2H, d), 5.80 (2H, s), 4.35 (2H, s) s), 2.95 (3 H, s), 2.48-2.43 (1 H, m), 0.64 (4 H, d).
Intermediate (A1e10): 1 H-NMR (DMSO-D 6 ) δ: 9.59 (1H, s), 7.56 (2H, d), 7.39-7.31 (4H, m), 7.26-7.23 (3H, m), 5.74 (2H, s), 4.87 (2H, s), 3.09 (3H, s).
Intermediate (A1e11): 1 H-NMR (DMSO-D 6 ) δ: 9.61 (1H, s), 7.56-7.54 (2H, m), 7.48-7.46 (1H, m), 7.26-7.20 (1H, m) ), 7.19-7.14 (4H, m), 5.76 (2H, s), 4.88-4.85 (1H, m), 4.59-4.56 (1H, m), 3.13 (3H, s), 2.02 (3H, s).
Intermediate (A1e12): 1 H-NMR (DMSO-D 6 ) δ: 9.59 (1H, s), 7.57-7.55 (2H, m), 7.26-7.23 (2H, m), 7.21-7.15 (3H, m) , 7.07-7.05 (1H, m), 5.75 (2H, s), 4.85 (2H, s), 3.08 (3H, s), 2.26 (3H, s).
Intermediate (A1e13): 1 H-NMR (DMSO-D 6 ) δ: 9.59 (1H, s), 7.56-7.54 (2H, m), 7.26-7.22 (4H, m), 7.13-7.11 (2H, m) ), 5.75 (2H, s), 4.83 (2H, s), 3.06 (3H, s), 2.24 (3H, s).
Intermediate (A1e14): 1 H-NMR (DMSO-D 6 ) δ: 9.61 (1H, s), 7.57 (2H, d), 7.46-7.42 (1H, m), 7.36-7.30 (1H, m), 7.27-7.21 (3H, m), 7.18-7.14 (1H, m), 5.76 (2H, s), 4.80 (2H, s), 3.17 (3H, s).
Intermediate (A1e15): 1 H-NMR (DMSO-D 6 ) δ: 9.60 (1H, s), 7.56 (2H, d), 7.29-7.23 (3H, m), 7.09-7.07 (1H, m), 7.04-7.02 (1H, m), 6.83-6.79 (1H, m), 5.76 (2H, s), 4.73 (2H, s), 3.87 (3H, s), 3.07 (3H, s).
Intermediate (A1e16): 1 H-NMR (DMSO-D 6 ) δ: 9.58 (1H, s), 7.64-7.62 (2H, m), 7.38-7.36 (2H, m), 5.77 (2H, s), 4.48 (2H, s), 3.04 (3H, s), 1.34 (9H, s).
Intermediate (A1e17): 1 H-NMR (DMSO-D 6 ) δ: 9.63 (1H, s), 7.68-7.66 (2H, m), 7.39-7.36 (2H, m), 5.81 (2H, s), 4.38 (2H, s), 3.29-3.25 (2H, m), 3.03 (3H, s), 2.49-2.46 (2H, m), 1.97 (3H, s).

式(A1f)

Figure 2019089711
で示される化合物において、R6、R8、R9及びR10の組合わせが下表に記載のいずれかの組合せである化合物。
Figure 2019089711
中間体(A1f1):1H-NMR (DMSO-D6) δ: 9.64 (1H, s), 7.67 (1H, s), 7.58-7.55 (2H, m), 7.36-7.34 (2H, m), 5.79 (2H, s), 4.16 (2H, s), 2.86 (3H, s).
中間体(A1f2):1H-NMR (DMSO-D6) δ: 9.65 (1H, s), 7.68 (1H, s), 7.62-7.58 (1H, m), 7.57-7.55 (1H, m), 7.36-7.34 (2H, m), 5.79 (2H, s), 4.14 (2H, d), 2.94 (2H, q), 1.16 (3H, t).
中間体(A1f3):1H-NMR (DMSO-D6) δ: 9.64 (1H, s), 7.67 (1H, br s), 7.60-7.54 (2H, m), 7.36-7.34 (2H, m), 5.78 (2H, s), 4.17 (2H, d), 3.10-3.06 (1H, m), 1.21 (6H, d).
中間体(A1f4):1H-NMR (DMSO-D6) δ: 9.78 (1H, s), 7.69-7.65 (2H, m), 7.58-7.55 (1H, m), 7.41-7.35 (2H, m), 6.08 (2H, s), 4.20 (2H, d, J = 6.2 Hz), 2.49-2.47 (1H, m), 0.90-0.85 (4H, m). Formula (A1 f)
Figure 2019089711
In the compounds shown by, a combination of R 6 , R 8 , R 9 and R 10 is any combination described in the following table.
Figure 2019089711
Intermediate (A1f1): 1 H-NMR (DMSO-D 6 ) δ: 9.64 (1H, s), 7.67 (1H, s), 7.58-7.55 (2H, m), 7.36-7.34 (2H, m), 5.79 (2H, s), 4.16 (2H, s), 2.86 (3H, s).
Intermediate (A1 f2): 1 H-NMR (DMSO-D 6 ) δ: 9.65 (1 H, s), 7.68 (1 H, s), 7.62-7.58 (1 H, m), 7.57-7.55 (1 H, m), 7.36-7.34 (2H, m), 5.79 (2H, s), 4.14 (2H, d), 2.94 (2H, q), 1.16 (3H, t).
Intermediate (A1f3): 1 H-NMR (DMSO-D 6 ) δ: 9.64 (1H, s), 7.67 (1H, br s), 7.60-7.54 (2H, m), 7.36-7.34 (2H, m) , 5.78 (2H, s), 4.17 (2H, d), 3.10-3.06 (1 H, m), 1.21 (6 H, d).
Intermediate (A1f4): 1 H-NMR (DMSO-D 6 ) δ: 9.78 (1H, s), 7.69-7.65 (2H, m), 7.58-7.55 (1H, m), 7.41-7.35 (2H, m) ), 6.08 (2H, s), 4.20 (2H, d, J = 6.2 Hz), 2.49-2.47 (1 H, m), 0.90-0.85 (4 H, m).

式(A1g)

Figure 2019089711
で示される化合物において、R11及びR12の組合わせが下表に記載のいずれかの組合せである化合物。
Figure 2019089711
中間体(A1g1):1H-NMR (DMSO-D6) δ: 9.69 (1H, s), 7.67 (2H, d), 7.36 (2H, d), 6.95 (1H, q), 5.87 (2H, s), 4.34 (2H, s), 2.57 (3H, d).
中間体(A1g2):1H-NMR (DMSO-D6) δ: 9.67 (1H, s), 7.68-7.66 (2H, m), 7.36-7.34 (2H, m), 7.07 (1H, t), 5.83 (2H, s), 4.32 (2H, s), 2.97-2.90 (2H, m), 1.04 (3H, t).
中間体(A1g3):1H-NMR (DMSO-D6) δ: 9.68 (1H, s), 7.68-7.65 (2H, m), 7.36 (2H, d), 7.09 (1H, t), 5.86 (2H, s), 4.32 (2H, s), 2.88-2.82 (2H, m), 1.47-1.38 (2H, m), 0.84 (3H, t).
中間体(A1g4):1H-NMR (DMSO-D6) δ: 9.67 (1H, s), 7.66 (2H, d), 7.36 (2H, d), 7.21 (1H, t), 5.83 (2H, s), 4.32 (2H, s), 2.80-2.76 (2H, m), 0.91 (1H, d), 0.45-0.41 (2H, m), 0.18-0.15 (2H, m).
中間体(A1g5):1H-NMR (DMSO-D6) δ: 9.68 (1H, s), 7.69-7.66 (2H, m), 7.41-7.39 (2H, m), 5.84 (2H, s), 4.42 (2H, s), 2.72 (6H, s).
中間体(A1g6):1H-NMR (DMSO-D6) δ: 9.67 (1H, s), 7.68-7.65 (2H, m), 7.42-7.39 (2H, m), 5.83 (2H, s), 4.44 (2H, s), 3.17-3.14 (4H, m), 1.81-1.77 (4H, m). Formula (A1g)
Figure 2019089711
In the compounds shown by, the combination of R 11 and R 12 is any combination described in the following table.
Figure 2019089711
Intermediate (A1g1): 1 H-NMR (DMSO-D 6 ) δ: 9.69 (1H, s), 7.67 (2H, d), 7.36 (2H, d), 6.95 (1H, q), 5.87 (2H, d) s), 4.34 (2H, s), 2.57 (3H, d).
Intermediate (A1g2): 1 H-NMR (DMSO-D 6 ) δ: 9.67 (1H, s), 7.68-7.66 (2H, m), 7.36-7.34 (2H, m), 7.07 (1H, t), 5.83 (2H, s), 4.32 (2H, s), 2.97-2.90 (2H, m), 1.04 (3H, t).
Intermediate (A1g3): 1 H-NMR (DMSO-D 6 ) δ: 9.68 (1H, s), 7.68-7.65 (2H, m), 7.36 (2H, d), 7.09 (1H, t), 5.86 ( 2H, s), 4.32 (2H, s), 2.88-2.82 (2H, m), 1.47-1.38 (2H, m), 0.84 (3H, t).
Intermediate (A1g4): 1 H-NMR (DMSO-D 6 ) δ: 9.67 (1H, s), 7.66 (2H, d), 7.36 (2H, d), 7.21 (1H, t), 5.83 (2H, 5) s), 4.32 (2H, s), 2.80-2.76 (2H, m), 0.91 (1H, d), 0.45-0.41 (2H, m), 0.18-0.15 (2H, m).
Intermediate (A1g5): 1 H-NMR (DMSO-D 6 ) δ: 9.68 (1H, s), 7.69-7.66 (2H, m), 7.41-7.39 (2H, m), 5.84 (2H, s), 4.42 (2H, s), 2.72 (6H, s).
Intermediate (A1g6): 1 H-NMR (DMSO-D 6 ) δ: 9.67 (1H, s), 7.68-7.65 (2H, m), 7.42-7.39 (2H, m), 5.83 (2H, s), 4.44 (2H, s), 3.17-3.14 (4H, m), 1.81-1.77 (4H, m).

Figure 2019089711
中間体(A1g7):1H-NMR (CDCl3) δ: 7.60-7.56 (2H, m), 6.99-6.95 (2H, m), 5.17 (2H, s), 4.83 (2H, s), 2.26 (3H, s).
Figure 2019089711
Intermediate (A1g7): 1 H-NMR (CDCl 3 ) δ: 7.60-7.56 (2H, m), 6.99-6.95 (2H, m), 5.17 (2H, s), 4.83 (2H, s), 2.26 (2. 3H, s).

Figure 2019089711
中間体(A1g8):1H-NMR (DMSO-D6) δ: 9.99 (1H, s), 8.56 (1H, s), 7.89 (1H, d), 7.84-7.81 (1H, m), 5.87 (2H, s), 4.60 (2H, s), 2.97 (3H, s).
Figure 2019089711
Intermediate (A1g8): 1 H-NMR (DMSO-D 6 ) δ: 9.99 (1H, s), 8.56 (1H, s), 7.89 (1H, d), 7.84-7.81 (1H, m), 5.87 (1H, s) 2H, s), 4.60 (2H, s), 2.97 (3H, s).

Figure 2019089711
中間体(A1g9):1H-NMR (DMSO-D6) δ: 9.63 (1H, s), 7.66 (2H, d), 7.33 (2H, d), 5.81 (2H, s), 4.09 (2H, s), 3.25 (2H, t), 3.08 (2H, t), 2.25-2.18 (2H, m).
Figure 2019089711
Intermediate (A1g9): 1 H-NMR (DMSO-D 6 ) δ: 9.63 (1 H, s), 7.66 (2 H, d), 7.33 (2 H, d), 5.81 (2 H, s), 4.09 (2 H, s), 3.25 (2H, t), 3.08 (2H, t), 2.25-2.18 (2H, m).

Figure 2019089711
中間体(A1g10):1H-NMR (DMSO-D6) δ: 9.63 (1H, s), 7.66 (2H, d), 7.33 (2H, d), 5.80 (2H, s), 4.26 (2H, s), 3.17 (4H, t), 2.07-2.01 (2H, m), 1.60-1.54 (2H, m).
Figure 2019089711
Intermediate (A1g10): 1 H-NMR (DMSO-D 6 ) δ: 9.63 (1H, s), 7.66 (2H, d), 7.33 (2H, d), 5.80 (2H, s), 4.26 (2H, 2) s), 3.17 (4H, t), 2.07-2.01 (2H, m), 1.60-1.54 (2H, m).

Figure 2019089711
中間体(A1g11):1H-NMR (DMSO-D6) δ: 9.60 (1H, s), 8.22 (1H, s), 7.88-7.83 (2H, m), 7.59-7.57 (2H, m), 7.44-7.38 (2H, m), 7.21 (2H, d), 5.77 (2H, s), 4.00 (2H, s).
Figure 2019089711
Intermediate (A1g11): 1 H-NMR (DMSO-D 6 ) δ: 9.60 (1H, s), 8.22 (1H, s), 7.88-7.83 (2H, m), 7.59-7.57 (2H, m), 7.44-7.38 (2H, m), 7.21 (2H, d), 5.77 (2H, s), 4.00 (2H, s).

Figure 2019089711
中間体(A1g12):1H-NMR (DMSO-D6) δ: 9.84 (1H, s), 7.57-7.45 (3H, m), 5.93 (2H, s), 4.44 (2H, s), 2.76 (6H, s).
Figure 2019089711
Intermediate (A1g12): 1 H-NMR (DMSO-D 6 ) δ: 9.84 (1H, s), 7.57-7.45 (3H, m), 5.93 (2H, s), 4.44 (2H, s), 2.76 (2. 6H, s).

Figure 2019089711
中間体(A1g13):1H-NMR (DMSO-D6) δ: 9.57 (1H, s), 7.68 (1H, s), 7.62-7.60 (2H, m), 7.30 (2H, d), 5.77 (2H, s), 4.09 (2H, s), 2.61 (6H, s).
Figure 2019089711
Intermediate (A1g13): 1 H-NMR (DMSO-D 6 ) δ: 9.57 (1H, s), 7.68 (1H, s), 7.62-7.60 (2H, m), 7.30 (2H, d), 5.77 (5 2H, s), 4.09 (2H, s), 2.61 (6H, s).

参考製造例2−1
参考製造例4−1に記載の中間体(A2c1)1.7g、エタノール20mL、及び50%−ヒドロキシルアミン水溶液1.9mLの混合物を加熱還流下、5時間撹拌した。室温に冷却後、沈殿物を濾取し、得られた沈殿物をエタノール50mLで洗浄し、減圧乾燥し、中間体(A1c1)を1.2g得た。

Figure 2019089711
中間体(A1c1):1H-NMR (DMSO-D6) δ: 9.70 (1H, s), 7.70-7.68 (2H, m), 7.41-7.39 (2H, m), 5.84 (2H, s), 4.50 (2H, s), 2.91 (3H, s). Reference Production Example 2-1
A mixture of 1.7 g of the intermediate (A2c1) described in Reference Production Example 4-1, 20 mL of ethanol, and 1.9 mL of 50% aqueous hydroxylamine solution was stirred for 5 hours under heating to reflux. After cooling to room temperature, the precipitate was collected by filtration, and the obtained precipitate was washed with 50 mL of ethanol and dried under reduced pressure to obtain 1.2 g of an intermediate (A1c1).
Figure 2019089711
Intermediate (A1c1): 1 H-NMR (DMSO-D 6 ) δ: 9.70 (1H, s), 7.70-7.68 (2H, m), 7.41-7.39 (2H, m), 5.84 (2H, s), 4.50 (2H, s), 2.91 (3H, s).

参考製造例2−2
参考製造例2−1に記載の方法に準じて製造した中間体化合物と、その物性値を以下に示す。
式(A1c)

Figure 2019089711
で示される化合物において、R8、R9、R10、R21及びR22の組合わせが下表に記載のいずれかの組合せである化合物。
Figure 2019089711
中間体(A1c2):1H-NMR (DMSO-D6) δ: 9.86 (1H, s), 7.58-7.56 (1H, m), 7.54-7.51 (1H, m), 7.48-7.44 (1H, m), 5.94 (2H, s), 4.56 (2H, s), 3.01 (3H, s).
中間体(A1c3):1H-NMR (DMSO-D6) δ: 9.70 (1H, s), 7.55-7.51 (1H, m), 7.29-7.24 (2H, m), 5.85 (2H, s), 4.55 (2H, s), 2.94 (3H, s). Reference Production Example 2-2
The intermediate compounds produced according to the method described in Reference Production Example 2-1 and the physical properties thereof are shown below.
Formula (A1c)
Figure 2019089711
And R 8 , R 9 , R 10 , R 21 and R 22 in any of the combinations shown in the following table.
Figure 2019089711
Intermediate (A1c2): 1 H-NMR (DMSO-D 6 ) δ: 9.86 (1H, s), 7.58 to 7.56 (1H, m), 7.54 to 7.51 (1H, m), 7.48 to 7.44 (1H, m) ), 5.94 (2H, s), 4.56 (2H, s), 3.01 (3H, s).
Intermediate (A1c3): 1 H-NMR (DMSO-D 6 ) δ: 9.70 (1H, s), 7.55 to 7.51 (1H, m), 7.29 to 7.24 (2H, m), 5.85 (2H, s), 4.55 (2H, s), 2.94 (3H, s).

式(A1d)

Figure 2019089711
で示される化合物において、R8、R9及びR10の組合わせが下表に記載の組合せである化合物。
Figure 2019089711
中間体(A1d1):1H-NMR (DMSO-D6) δ: 9.68 (1H, s), 7.74-7.72 (1H, m), 7.67-7.64 (1H, m), 7.42-7.40 (2H, m), 5.82 (2H, s), 4.49 (2H, s), 2.91 (3H, s). Formula (A1d)
Figure 2019089711
Compounds in which R 8 , R 9 and R 10 have the combinations given in the following table.
Figure 2019089711
Intermediate (A1d1): 1 H-NMR (DMSO-D 6 ) δ: 9.68 (1H, s), 7.74-7.72 (1H, m), 7.67-7.64 (1H, m), 7.42-7.40 (2H, m) ), 5.82 (2H, s), 4.49 (2H, s), 2.91 (3H, s).

参考製造例3−1
4−(ブロモメチル)ベンゾニトリル2.0g、エタノール50mL、及びナトリウムメタンチオラート0.72gの混合物を加熱還流下、5時間撹拌した。室温に冷却後、反応混合物に水20mLを加えた後、ジエチルエーテルで抽出した。有機層を飽和食塩水で洗浄し、乾燥、減圧濃縮し、中間体(A2a1)を1.7g得た。

Figure 2019089711
中間体(A2a1):1H-NMR (CDCl3) δ: 7.63-7.61 (2H, m), 7.43-7.41 (2H, m), 3.70 (2H, s), 1.99 (3H, s). Reference Production Example 3-1
A mixture of 2.0 g of 4- (bromomethyl) benzonitrile, 50 mL of ethanol, and 0.72 g of sodium methanethiolate was stirred for 5 hours while heating to reflux. After cooling to room temperature, 20 mL of water was added to the reaction mixture and then extracted with diethyl ether. The organic layer was washed with saturated brine, dried and concentrated under reduced pressure to give 1.7 g of an intermediate (A2a1).
Figure 2019089711
Intermediate (A2a1): 1 H-NMR (CDCl 3 ) δ: 7.63-7.61 (2H, m), 7.43-7.41 (2H, m), 3.70 (2H, s), 1.99 (3H, s).

参考製造例3−2
参考製造例3−1に記載の方法に準じて製造した中間体化合物と、その物性値を以下に示す。
式(A2a)

Figure 2019089711
で示される化合物において、R8、R9及びR10の組合わせが下表に記載のいずれかの組合せである化合物。
Figure 2019089711
中間体(A2a2):1H-NMR (CDCl3) δ: 7.62-7.60 (2H, m), 7.44-7.42 (2H, m), 3.74 (2H, s), 2.42 (2H, q), 1.23 (3H, t).
中間体(A2a3):1H-NMR (CDCl3) δ: 7.61-7.59 (2H, m), 7.45-7.44 (2H, m), 3.76 (2H, s), 2.80-2.73 (1H, m), 1.25 (6H, d, J = 6.6 Hz). Reference Production Example 3-2
Intermediate compounds produced according to the method described in Reference Production Example 3-1 and physical property values thereof are shown below.
Formula (A2a)
Figure 2019089711
In the compounds shown by, the combination of R 8 , R 9 and R 10 is any combination described in the following table.
Figure 2019089711
Intermediate (A2a2): 1 H-NMR (CDCl 3 ) δ: 7.62 to 7.60 (2H, m), 7.44 to 7.42 (2H, m), 3.74 (2H, s), 2.42 (2H, q), 1.23 (1.23) 3H, t).
Intermediate (A2a3): 1 H-NMR (CDCl 3 ) δ: 7.61-7.59 (2H, m), 7.45-7.44 (2H, m), 3.76 (2H, s), 2.80-2.73 (1H, m), 1.25 (6H, d, J = 6.6 Hz).

式(A2b)

Figure 2019089711
で示される化合物において、R8、R9及びR10の組合わせが下表に記載の組合せである化合物。
Figure 2019089711
中間体(A2b1):1H-NMR (CDCl3) δ: 7.62-7.61 (1H, m), 7.57-7.56 (1H, m), 7.55-7.54 (1H, m), 7.45-7.41 (1H, m), 3.68 (2H, s), 2.00 (3H, s). Formula (A2b)
Figure 2019089711
Compounds in which R 8 , R 9 and R 10 have the combinations given in the following table.
Figure 2019089711
Intermediate (A2b1): 1 H-NMR (CDCl 3 ) δ: 7.62 to 7.61 (1H, m), 7.57 to 7.56 (1H, m), 7.55 to 7.54 (1H, m), 7.45 to 7.41 (1H, m) ), 3.68 (2H, s), 2.00 (3H, s).

参考製造例4−1
4−(ブロモメチル)ベンゾニトリル1.5g、1-メチル−2−ピロリドン50mL、及びメタンスルフィン酸ナトリウム0.78gの混合物を100℃で、10時間撹拌した。室温に冷却後、反応混合物に水100mLを加えて、酢酸エチルで抽出した。有機層を飽和食塩水で洗浄し、乾燥、減圧濃縮し、中間体(A2c1)を1.8g得た。

Figure 2019089711
中間体(A2c1):1H-NMR (CDCl3) δ: 7.73 (2H, d), 7.56 (2H, d), 4.31 (2H, s), 2.85 (3H, s). Reference Production Example 4-1
A mixture of 1.5 g of 4- (bromomethyl) benzonitrile, 50 mL of 1-methyl-2-pyrrolidone, and 0.78 g of sodium methanesulfinate was stirred at 100 ° C. for 10 hours. After cooling to room temperature, 100 mL of water was added to the reaction mixture and extracted with ethyl acetate. The organic layer was washed with saturated brine, dried and concentrated under reduced pressure to give 1.8 g of an intermediate (A2c1).
Figure 2019089711
Intermediate (A2c1): 1 H-NMR (CDCl 3 ) δ: 7.73 (2H, d), 7.56 (2H, d), 4.31 (2H, s), 2.85 (3H, s).

参考製造例4−2
参考製造例4−1に記載の方法に準じて製造した中間体化合物と、その物性値を以下に示す。
式(A2c)

Figure 2019089711
で示される化合物において、R8、R9、R10、R21及びR22の組合わせが下表に記載のいずれかの組合せである化合物。
Figure 2019089711
中間体(A2c2):1H-NMR (DMSO-D6) δ: 7.97-7.95 (1H, m), 7.79-7.77 (1H, m), 7.70-7.66 (1H, m), 4.69 (2H, s), 3.06 (3H, s).
中間体(A2c3):1H-NMR (DMSO-D6) δ: 8.02-7.98 (1H, m), 7.58-7.56 (1H, m), 7.48-7.45 (1H, m), 4.68 (2H, s), 2.97 (3H, s). Reference Production Example 4-2
The intermediate compounds produced according to the method described in Reference Production Example 4-1 and the physical properties thereof are shown below.
Formula (A2c)
Figure 2019089711
And R 8 , R 9 , R 10 , R 21 and R 22 in any of the combinations shown in the following table.
Figure 2019089711
Intermediate (A2c2): 1 H-NMR (DMSO-D 6 ) δ: 7.97-7.95 (1H, m), 7.79-7.77 (1H, m), 7.70-7.66 (1H, m), 4.69 (2H, s) ), 3.06 (3H, s).
Intermediate (A2c3): 1 H-NMR (DMSO-D 6 ) δ: 8.02 to 7.98 (1H, m), 7.58 to 7.56 (1H, m), 7.48 to 7.45 (1H, m), 4.68 (2H, s) ), 2.97 (3H, s).

式(A2d)

Figure 2019089711
で示される化合物において、R8、R9及びR10の組合わせが下表に記載の組合せである化合物。
Figure 2019089711
中間体(A2d1):1H-NMR (CDCl3) δ: 7.74-7.69 (3H, m), 7.57 (1H, t), 4.29 (2H, s), 2.86 (3H, s). Formula (A2d)
Figure 2019089711
Compounds in which R 8 , R 9 and R 10 have the combinations given in the following table.
Figure 2019089711
Intermediate (A2d1): 1 H-NMR (CDCl 3 ) δ: 7.74-7.69 (3H, m), 7.57 (1H, t), 4.29 (2H, s), 2.86 (3H, s).

Figure 2019089711
中間体(A2d2):1H-NMR (DMSO-D6) δ: 8.76-8.75 (1H, m), 8.12-8.07 (2H, m), 4.73 (2H, s), 3.01 (3H, s).
Figure 2019089711
Intermediate (A2d2): 1 H-NMR (DMSO-D 6 ) δ: 8.76-8.75 (1H, m), 8.12-8.07 (2H, m), 4.73 (2H, s), 3.01 (3H, s).

参考製造例5−1
室温で、4−(アミノメチル)ベンゾニトリル1.0g、及びテトラヒドロフラン20mLの混合物に、メタンスルホニルクロライド1.0mL及びトリエチルアミン1.6mLを順次加えた後、10時間撹拌した。反応混合物に水20mLを加え、酢酸エチルで抽出した。有機層を飽和食塩水で洗浄し、乾燥、減圧濃縮し、中間体(A2e1)を1.1g得た。

Figure 2019089711
中間体(A2e1):1H-NMR (DMSO-D6) δ: 7.85-7.82 (2H, m), 7.76 (1H, br s), 7.56-7.54 (2H, m), 4.26 (2H, s), 2.92 (3H, s). Reference Production Example 5-1
After sequentially adding 1.0 mL of methanesulfonyl chloride and 1.6 mL of triethylamine to a mixture of 1.0 g of 4- (aminomethyl) benzonitrile and 20 mL of tetrahydrofuran at room temperature, the mixture was stirred for 10 hours. To the reaction mixture was added 20 mL of water and extracted with ethyl acetate. The organic layer was washed with saturated brine, dried and concentrated under reduced pressure to give 1.1 g of an intermediate (A2e1).
Figure 2019089711
Intermediate (A2e1): 1 H-NMR (DMSO-D 6 ) δ: 7.85-7.82 (2H, m), 7.76 (1H, br s), 7.56-7.54 (2H, m), 4.26 (2H, s) , 2.92 (3H, s).

参考製造例5−2
参考製造例5−1に記載の方法に準じて製造した中間体化合物と、その物性値を以下に示す。
式(A2e)

Figure 2019089711
で示される化合物において、R6、R8、R9及びR10の組合わせが下表に記載のいずれかの組合せである化合物。
Figure 2019089711
中間体(A2e2):1H-NMR (CDCl3) δ: 7.68-7.66 (2H, m), 7.50-7.48 (2H, m), 4.66 (1H, br s), 4.38 (2H, d), 3.02 (2H, q), 1.37 (3H, t).
中間体(A2e3):1H-NMR (CDCl3) δ: 7.68-7.66 (2H, m), 7.50-7.48 (2H, m), 4.41 (3H, br s), 3.16-3.13 (1H, m), 1.39 (6H, d).
中間体(A2e4):1H-NMR (CDCl3) δ: 7.67-7.63 (2H, m), 7.52-7.49 (2H, m), 5.15 (1H, s), 4.42-4.39 (2H, m), 2.40-2.33 (1H, m), 1.16-1.11 (2H, m), 1.00-0.93 (2H, m).
中間体(A2e5):1H-NMR (CDCl3) δ: 7.68-7.66 (2H, m), 7.50-7.48 (2H, m), 4.65-4.64 (1H, m), 4.38 (2H, d), 2.99-2.95 (2H, m), 1.89-1.80 (2H, m), 1.04 (3H, t).
中間体(A2e6):1H-NMR (CDCl3) δ: 7.68-7.65 (2H, m), 7.50-7.48 (2H, m), 4.74 (1H, t), 4.38 (2H, d), 3.00-2.96 (2H, m), 1.81-1.73 (2H, m), 1.47-1.38 (2H, m), 0.93 (3H, t).
中間体(A2e7):1H-NMR (CDCl3) δ: 7.67 (2H, d), 7.49 (2H, d), 4.70-4.67 (1H, m), 4.37 (2H, d), 2.89 (2H, d), 2.30-2.20 (1H, m), 1.09 (6H, d). Reference Production Example 5-2
Intermediate compounds produced according to the method described in Reference Production Example 5-1 and physical property values thereof are shown below.
Formula (A2e)
Figure 2019089711
In the compounds shown by, a combination of R 6 , R 8 , R 9 and R 10 is any combination described in the following table.
Figure 2019089711
Intermediate (A2e2): 1 H-NMR (CDCl 3 ) δ: 7.68-7.66 (2H, m), 7.50-1.48 (2H, m), 4.66 (1H, br s), 4.38 (2H, d), 3.02 (2H, q), 1.37 (3H, t).
Intermediate (A2e3): 1 H-NMR (CDCl 3 ) δ: 7.68-7.66 (2H, m), 7.50-1.48 (2H, m), 4.41 (3H, br s), 3.16-3. 13 (1H, m) , 1.39 (6H, d).
Intermediate (A2e4): 1 H-NMR (CDCl 3 ) δ: 7.67-7.63 (2H, m), 7.52-7.49 (2H, m), 5.15 (1H, s), 4.42-4.39 (2H, m), 2.40-2.33 (1 H, m), 1.16-1.11 (2 H, m), 1.00-0.93 (2 H, m).
Intermediate (A2e5): 1 H-NMR (CDCl 3 ) δ: 7.68-7.66 (2H, m), 7.50-7.48 (2H, m), 4.65-4.64 (1H, m), 4.38 (2H, d), 2.99-2.95 (2H, m), 1.89-1.80 (2H, m), 1.04 (3H, t).
Intermediate (A2e6): 1 H-NMR (CDCl 3 ) δ: 7.68-7.65 (2H, m), 7.50-1.48 (2H, m), 4.74 (1H, t), 4.38 (2H, d), 3.00- 2.96 (2H, m), 1.81-1.73 (2H, m), 1.47-1.38 (2H, m), 0.93 (3H, t).
Intermediate (A2e7): 1 H-NMR (CDCl 3 ) δ: 7.67 (2H, d), 7.49 (2H, d), 4.704 to 4.67 (1H, m), 4.37 (2H, d), 2.89 (2H, d) d), 2.30-2.20 (1 H, m), 1.09 (6 H, d).

式(A2f)

Figure 2019089711
で示される化合物において、R6、R8、R9及びR10の組合わせが下表に記載のいずれかの組合せである化合物。
Figure 2019089711
中間体(A2f1):1H-NMR (CDCl3) δ: 7.67-7.62 (3H, m), 7.53-7.48 (1H, m), 4.76 (1H, br s), 4.38 (2H, d, J = 6.6 Hz), 2.96 (3H, s).
中間体(A2f2):1H-NMR (CDCl3) δ: 7.66-7.60 (3H, m), 7.52-7.47 (1H, m), 5.04 (1H, s), 4.36-4.34 (2H, m), 3.04-2.98 (2H, m), 1.38-1.33 (3H, m).
中間体(A2f3):1H-NMR (CDCl3) δ: 7.66-7.59 (3H, m), 7.51-7.47 (1H, m), 4.84 (1H, s), 4.36 (2H, s), 3.17-3.10 (1H, m), 1.38 (6H, d).
中間体(A2f4):1H-NMR (CDCl3) δ: 7.69-7.67 (1H, m), 7.65-7.58 (2H, m), 7.51-7.45 (1H, m), 5.01 (1H, s), 4.39-4.38 (2H, m), 2.42-2.34 (1H, m), 1.18-1.10 (2H, m), 1.04-0.93 (2H, m). Formula (A2f)
Figure 2019089711
In the compounds shown by, a combination of R 6 , R 8 , R 9 and R 10 is any combination described in the following table.
Figure 2019089711
Intermediate (A2f1): 1 H-NMR (CDCl 3 ) δ: 7.67-7.62 (3H, m), 7.53-7.48 (1H, m), 4.76 (1H, br s), 4.38 (2H, d, J = 6.6 Hz), 2.96 (3H, s).
Intermediate (A2f2): 1 H-NMR (CDCl 3 ) δ: 7.66-7.60 (3H, m), 7.52-7.47 (1H, m), 5.04 (1H, s), 4.36-4.34 (2H, m), 3.04-2.98 (2H, m), 1.38-1.33 (3H, m).
Intermediate (A2f3): 1 H-NMR (CDCl 3 ) δ: 7.66-7.59 (3H, m), 7.51-7.47 (1H, m), 4.84 (1H, s), 4.36 (2H, s), 3.17- 3.10 (1 H, m), 1. 38 (6 H, d).
Intermediate (A2f4): 1 H-NMR (CDCl 3 ) δ: 7.69-7.67 (1H, m), 7.65-7.58 (2H, m), 7.51-7.45 (1H, m), 5.01 (1H, s), 4.39-4.38 (2H, m), 2.42-2.34 (1H, m), 1.18-1.10 (2H, m), 1.04-0.93 (2H, m).

Figure 2019089711
中間体(A2f5):1H-NMR (CDCl3) δ: 7.68-7.64 (2H, m), 7.49-7.47 (2H, m), 4.61 (1H, s), 4.30 (2H, d), 2.78 (6H, s).
Figure 2019089711
Intermediate (A2f5): 1 H-NMR (CDCl 3 ) δ: 7.68-7.64 (2H, m), 7.49-7.47 (2H, m), 4.61 (1H, s), 4.30 (2H, d), 2.78 (2. 6H, s).

参考製造例6−1
0℃で、(4−シアノフェニル)メタンスルホニルクロライド0.5g、及びテトラヒドロフラン5mLの混合物に、プロピルアミン0.27g加えた後、室温で5時間撹拌した。反応混合物に水10mLを加え、酢酸エチルで抽出した。有機層を飽和食塩水で洗浄し、乾燥、減圧濃縮し、得られた残渣をシリカゲルカラムクロマトグラフィーに付し、中間体(A2g3)を0.4g得た。

Figure 2019089711
中間体(A2g3):1H-NMR (CDCl3) δ: 7.71-7.68 (2H, m), 7.54-7.52 (2H, m), 4.29 (2H, s), 4.21 (1H, t), 3.02-2.97 (2H, m), 1.59-1.49 (2H, m), 0.92 (3H, t). Reference Production Example 6-1
After 0.27 g of propylamine was added to a mixture of 0.5 g of (4-cyanophenyl) methanesulfonyl chloride and 5 mL of tetrahydrofuran at 0 ° C., the mixture was stirred at room temperature for 5 hours. 10 mL of water was added to the reaction mixture, and extracted with ethyl acetate. The organic layer was washed with saturated brine, dried and concentrated under reduced pressure, and the obtained residue was subjected to silica gel column chromatography to obtain 0.4 g of an intermediate (A2g3).
Figure 2019089711
Intermediate (A2g3): 1 H-NMR (CDCl 3 ) δ: 7.71-7.68 (2H, m), 7.54-7.52 (2H, m), 4.29 (2H, s), 4.21 (1H, t), 3.02- 2.97 (2H, m), 1.59-1.49 (2H, m), 0.92 (3H, t).

参考製造例6−2
参考製造例6−1に記載の方法に準じて製造した中間体化合物と、その物性値を以下に示す。
式(A2g)

Figure 2019089711
で示される化合物において、R11及びR12の組合わせが下表に記載の組合せである化合物。
Figure 2019089711
中間体(A2g1):1H-NMR (CDCl3) δ: 7.70 (2H, d), 7.53 (2H, d), 4.30 (2H, s), 4.20 (1H, br s), 2.75-2.73 (3H, m).
中間体(A2g2):1H-NMR (CDCl3) δ: 7.70-7.68 (2H, m), 7.54-7.52 (2H, m), 4.29 (2H, s), 3.11-3.04 (2H, m), 1.17 (3H, t).
中間体(A2g4):1H-NMR (CDCl3) δ: 7.71-7.68 (2H, m), 7.55-7.52 (2H, m), 4.31 (2H, s), 2.89 (2H, dd), 1.01-0.94 (1H, m), 0.59-0.54 (2H, m), 0.22-0.18 (2H, m).
中間体(A2g5):1H-NMR (CDCl3) δ: 7.70 (2H, d, J = 8.2 Hz), 7.54 (2H, d, J = 8.2 Hz), 4.24 (2H, s), 2.80 (6H, s).
中間体(A2g6):1H-NMR (CDCl3) δ: 7.70-7.67 (2H, m), 7.55-7.52 (2H, m), 4.27 (2H, s), 3.24-3.21 (4H, m), 1.89-1.86 (4H, m). Reference Production Example 6-2
Intermediate compounds produced according to the method described in Reference Production Example 6-1 and physical properties thereof are shown below.
Formula (A2g)
Figure 2019089711
In the compounds shown by, the combination of R 11 and R 12 is a combination described in the following table.
Figure 2019089711
Intermediate (A2g1): 1 H-NMR (CDCl 3 ) δ: 7.70 (2H, d), 7.53 (2H, d), 4.30 (2H, s), 4.20 (1H, br s), 2.75-2.73 (3H , m).
Intermediate (A2g2): 1 H-NMR (CDCl 3 ) δ: 7.70-7.68 (2H, m), 7.54-7.52 (2H, m), 4.29 (2H, s), 3.11-3.04 (2H, m), 1.17 (3H, t).
Intermediate (A2g4): 1 H-NMR (CDCl 3 ) δ: 7.71-7.68 (2H, m), 7.55-7.52 (2H, m), 4.31 (2H, s), 2.89 (2H, dd), 1.01- 0.94 (1 H, m), 0.59-0.54 (2 H, m), 0.22-0.18 (2 H, m).
Intermediate (A2g5): 1 H-NMR (CDCl 3 ) δ: 7.70 (2H, d, J = 8.2 Hz), 7.54 (2H, d, J = 8.2 Hz), 4.24 (2H, s), 2.80 (6H , s).
Intermediate (A2g6): 1 H-NMR (CDCl 3 ) δ: 7.70-7.67 (2H, m), 7.55-7.52 (2H, m), 4.27 (2H, s), 3.24-3.21 (4H, m), 1.89-1.86 (4H, m).

Figure 2019089711
中間体(A2g7):1H-NMR (CDCl3) δ: 7.67 (1H, t), 7.53-7.50 (1H, m), 7.45-7.42 (1H, m), 4.32-4.31 (2H, m), 2.81 (6H, s).
Figure 2019089711
Intermediate (A2g7): 1 H-NMR (CDCl 3 ) δ: 7.67 (1H, t), 7.53-7.50 (1H, m), 7. 45-7. 42 (1H, m), 4.32-4. 31 (2H, m), 2.81 (6H, s).

参考製造例7−1
0℃で、N−シクロプロピルメタンスルホンアミド0.3g及びN,N−ジメチルホルムアミド20mLの混合物に、水素化ナトリウム(60%、油性)0.1gを加え、0.5時間撹拌した。反応混合物に4−シアノベンジルブロマイド0.5gを加え、室温で12時間撹拌した。反応混合物に水10mLを加え、酢酸エチルで抽出した。有機層を飽和食塩水で洗浄し、乾燥、減圧濃縮し、得られた残渣をシリカゲルカラムクロマトグラフィーに付し、中間体(A2e8)を0.4g得た。

Figure 2019089711
中間体(A2e8):1H-NMR (CDCl3) δ: 7.67-7.65 (2H, m), 7.53-7.51 (2H, m), 4.47 (2H, s), 2.89 (3H, s), 2.42-2.37 (1H, m), 0.81-0.76 (4H, m). Reference Production Example 7-1
At 0 ° C., 0.1 g of sodium hydride (60%, oily) was added to a mixture of 0.3 g of N-cyclopropylmethanesulfonamide and 20 mL of N, N-dimethylformamide, and the mixture was stirred for 0.5 hours. 0.5 g of 4-cyanobenzyl bromide was added to the reaction mixture, and the mixture was stirred at room temperature for 12 hours. 10 mL of water was added to the reaction mixture, and extracted with ethyl acetate. The organic layer was washed with saturated brine, dried and concentrated under reduced pressure, and the obtained residue was subjected to silica gel column chromatography to obtain 0.4 g of an intermediate (A2e8).
Figure 2019089711
Intermediate (A2e8): 1 H-NMR (CDCl 3 ) δ: 7.67-7.65 (2H, m), 7.53 to 7.51 (2H, m), 4.47 (2H, s), 2.89 (3H, s), 2.42- 2.37 (1 H, m), 0.81-0.76 (4 H, m).

参考製造例7−2
参考製造例7−1に記載の方法に準じて製造した中間体化合物と、その物性値を以下に示す。
式(A2e)

Figure 2019089711
で示される化合物において、R6、R8、R9及びR10の組合せが下表に記載のいずれかの組合せである化合物。
Figure 2019089711
中間体(A2e9):1H-NMR (CDCl3) δ: 7.58-7.56 (2H, m), 7.41-7.39 (2H, m), 7.37-7.30 (3H, m), 7.28-7.25 (2H, m), 4.91 (2H, s), 2.98 (3H, s).
中間体(A2e10):1H-NMR (CDCl3) δ: 7.58-7.55 (2H, m), 7.36-7.34 (2H, m), 7.25-7.19 (3H, m), 7.16-7.14 (1H, m), 4.83-4.69 (2H, m), 2.99 (3H, s), 2.12 (3H, s).
中間体(A2e11):1H-NMR (CDCl3) δ: 7.59-7.56 (2H, m), 7.42-7.40 (2H, m), 7.24-7.21 (1H, m), 7.11-7.04 (3H, m), 4.89 (2H, s), 2.97 (3H, s), 2.32 (3H, s).
中間体(A2e12):1H-NMR (CDCl3) δ: 7.58-7.55 (2H, m), 7.41-7.39 (2H, m), 7.13 (4H, s), 4.87 (2H, s), 2.96 (3H, s), 2.31 (3H, s).
中間体(A2e13):1H-NMR (CDCl3) δ: 7.59-7.57 (2H, m), 7.51-7.48 (1H, m), 7.42 (2H, d), 7.33-7.31 (1H, m), 7.18-7.14 (1H, m), 7.09-7.06 (1H, m), 4.85 (2H, s), 3.04 (3H, d).
中間体(A2e14):1H-NMR (CDCl3) δ: 7.57-7.54 (2H, m), 7.40 (2H, d), 7.31-7.27 (1H, m), 7.09-7.07 (1H, m), 6.96-6.93 (1H, m), 6.87-6.83 (1H, m), 4.82 (2H, s), 3.93 (3H, s), 2.99 (3H, s).
中間体(A2e15):1H-NMR (CDCl3) δ: 7.65-7.63 (2H, m), 7.54-7.51 (2H, m), 4.57 (2H, s), 3.01 (3H, s), 1.43 (9H, s).
中間体(A2e16):1H-NMR (CDCl3) δ: 7.64 (2H, d), 7.50 (2H, d), 4.39 (2H, s), 4.24-4.33 (1H, m), 2.90 (3H, s), 1.36-1.90 (8H, m)
中間体(A2e17):1H-NMR (CDCl3) δ: 7.63 (2H, d), 7.53 (2H, d), 4.42 (2H, s), 3.69-3.76 (1H, m), 2.88 (3H, s), 1.77 (4H, d), 1.58-1.64 (1H, m), 1.28-1.33 (5H, m).
中間体(A2e18):1H-NMR (CDCl3) δ: 7.69-7.66 (2H, m), 7.52-7.50 (2H, m), 4.48 (2H, s), 3.40 (2H, t), 2.99 (3H, s), 2.56 (2H, t), 2.07 (3H, s). Reference Production Example 7-2
Intermediate compounds produced according to the method described in Reference Production Example 7-1 and physical property values thereof are shown below.
Formula (A2e)
Figure 2019089711
In the compounds shown by, the combination of R 6 , R 8 , R 9 and R 10 is any combination described in the table below.
Figure 2019089711
Intermediate (A2e9): 1 H-NMR (CDCl 3 ) δ: 7.58 to 7.56 (2H, m), 7.41 to 7.39 (2H, m), 7.37 to 7.30 (3H, m), 7.28 to 7.25 (2H, m) ), 4.91 (2H, s), 2.98 (3H, s).
Intermediate (A2e10): 1 H-NMR (CDCl 3 ) δ: 7.58 to 7.55 (2H, m), 7.36 to 7.34 (2H, m), 7.25 to 7.19 (3H, m), 7.16 to 7.14 (1H, m) ), 4.83-4.69 (2H, m), 2.99 (3H, s), 2.12 (3H, s).
Intermediate (A2e11): 1 H-NMR (CDCl 3 ) δ: 7.59-7.56 (2H, m), 7.42-7.40 (2H, m), 7.24-7.21 (1H, m), 711-7.04 (3H, m) ), 4.89 (2H, s), 2.97 (3H, s), 2.32 (3H, s).
Intermediate (A2e12): 1 H-NMR (CDCl 3 ) δ: 7.58 to 7.55 (2H, m), 7.41-7.39 (2H, m), 7.13 (4H, s), 4.87 (2H, s), 2.96 (2. 3H, s), 2.31 (3H, s).
Intermediate (A2e13): 1 H-NMR (CDCl 3 ) δ: 7.59 to 7.57 (2H, m), 7.51 to 7.48 (1H, m), 7.42 (2H, d), 7.33 to 7.31 (1H, m), 7.18-7.14 (1 H, m), 7.09-7.06 (1 H, m), 4. 85 (2 H, s), 3.04 (3 H, d).
Intermediate (A2e14): 1 H-NMR (CDCl 3 ) δ: 7.57-7.54 (2H, m), 7.40 (2H, d), 7.31-7.27 (1H, m), 7.09-7.07 (1H, m), 6.96-6.93 (1H, m), 6.87-6.83 (1H, m), 4.82 (2H, s), 3.93 (3H, s), 2.99 (3H, s).
Intermediate (A2e15): 1 H-NMR (CDCl 3 ) δ: 7.65-7.63 (2H, m), 7.54-7.51 (2H, m), 4.57 (2H, s), 3.01 (3H, s), 1.43 (1.42) 9H, s).
Intermediate (A2e16): 1 H-NMR (CDCl 3 ) δ: 7.64 (2H, d), 7.50 (2H, d), 4.39 (2H, s), 4.24-4.33 (1H, m), 2.90 (3H, 3) s), 1.36 to 1.90 (8H, m)
Intermediate (A2e17): 1 H-NMR (CDCl 3 ) δ: 7.63 (2H, d), 7.53 (2H, d), 4.42 (2H, s), 3.69-3.76 (1H, m), 2.88 (3H, 3) s), 1.77 (4H, d), 1.58-1.64 (1H, m), 1.28-1.33 (5H, m).
Intermediate (A2e18): 1 H-NMR (CDCl 3 ) δ: 7.69-7.66 (2H, m), 7.52-7.50 (2H, m), 4.48 (2H, s), 3.40 (2H, t), 2.99 (2.99) 3H, s), 2.56 (2H, t), 2.07 (3H, s).

Figure 2019089711
中間体(A2e19):1H-NMR (CDCl3) δ: 7.67-7.65 (2H, m), 7.49-7.47 (2H, m), 4.36 (2H, s), 3.23 (2H, t), 3.12 (2H, t), 2.28-2.22 (2H, m), 1.70-1.64 (2H, m).
Figure 2019089711
Intermediate (A2e19): 1 H-NMR (CDCl 3 ) δ: 7.67-7.65 (2H, m), 7.49-7.47 (2H, m), 4.36 (2H, s), 3.23 (2H, t), 3.12 (3) 2H, t), 2.28-2.22 (2H, m), 1. 70-1. 64 (2H, m).

参考製造例8−1
0℃で、4−シアノフェノール2.0g及びN,N−ジメチルホルムアミド40mLの混合物に、水素化ナトリウム(60%、油性)0.8gを加え、0.5時間撹拌した。反応混合物にクロロメチルメチルスルフィド2.4gを加え、室温で12時間撹拌した。反応混合物に水20mLを加え、酢酸エチルで抽出した。有機層を飽和食塩水で洗浄し、乾燥、減圧濃縮し、得られた残渣をシリカゲルカラムクロマトグラフィーに付し、中間体(A2h1)を3.0g得た。

Figure 2019089711
中間体(A2h1):1H-NMR (CDCl3) δ: 7.62-7.60 (2H, m), 7.02-7.00 (2H, m), 5.19 (2H, s), 2.26 (3H, s). Reference Production Example 8-1
At 0 ° C., 0.8 g of sodium hydride (60%, oily) was added to a mixture of 2.0 g of 4-cyanophenol and 40 mL of N, N-dimethylformamide and stirred for 0.5 hours. To the reaction mixture, 2.4 g of chloromethyl methyl sulfide was added and stirred at room temperature for 12 hours. To the reaction mixture was added 20 mL of water and extracted with ethyl acetate. The organic layer was washed with saturated brine, dried and concentrated under reduced pressure, and the obtained residue was subjected to silica gel column chromatography to obtain 3.0 g of an intermediate (A2h1).
Figure 2019089711
Intermediate (A2h1): 1 H-NMR (CDCl 3 ) δ: 7.62-7.60 (2H, m), 7.02-7.00 (2H, m), 5.19 (2H, s), 2.26 (3H, s).

本明細書中、Meはメチル基を表し、Etはエチル基を表し、Prはプロピル基を表し、i−Prはイソプロピル基を表し、c−Prはシクロプロピル基を表し、Buはブチル基を表し、i−Buはイソブチル基を表し、t−Buはtert−ブチル基を表し、c−Pentylはシクロペンチル基を表し、c−Hexylはシクロヘキシル基を表し、Phはフェニル基を表し、Bnはベンジル基、Pyはピリジル基を表す。   In the present specification, Me represents a methyl group, Et represents an ethyl group, Pr represents a propyl group, i-Pr represents an isopropyl group, c-Pr represents a cyclopropyl group, and Bu represents a butyl group. I-Bu represents an isobutyl group, t-Bu represents a tert-butyl group, c-Pentyl represents a cyclopentyl group, c-Hexyl represents a cyclohexyl group, Ph represents a phenyl group, and Bn represents benzyl The group, Py represents a pyridyl group.

式(II)

Figure 2019089711
〔式中、R21、R22、R23及びR24は、水素原子又は群Iで表される置換基を表し、R25は群A及び群Fからなる群より選ばれる1以上の置換基を有していてもよいC1−C6アルキル基、1以上のハロゲン原子を有していてもよいC3−C6シクロアルキル基又は1以上のハロゲン原子を有していてもよいフェニル基を表す。〕
で表される化合物において、R21、R22、R23、R24及びR25の組合わせが、下記に示される置換基番号RA1〜RA112のいずれかに記載の組合わせである化合物(以下、置換基番号RA1〜RA112の化合物を本発明化合物RA1〜RA112と表し、本発明化合物RA1〜RA112をまとめて本発明化合物RAと表す)は、上記の製造法に記載の方法に準じて得ることができる。
なお、置換基番号RA1〜RA112とは、式(II)で表される化合物における、R21、R22、R23、R24及びR25の組合わせを表すものであり、以下、[置換基番号;R21,R22,R23,R24,R25]と記す。
例えば、置換基番号RA4とは、R21、R22、R23、及びR24が水素原子であり、R25がイソプロピル基である組合せを表す。 Formula (II)
Figure 2019089711
[Wherein, R 21 , R 22 , R 23 and R 24 each represent a hydrogen atom or a substituent represented by group I, and R 25 represents one or more substituents selected from the group consisting of group A and group F] And an optionally substituted C 1 -C 6 alkyl group, a C 3 -C 6 cycloalkyl group optionally having one or more halogen atoms, or a phenyl group optionally having one or more halogen atoms. ]
In the compound represented by this, the compound in which the combination of R 21 , R 22 , R 23 , R 24 and R 25 is a combination described in any of the substituent numbers RA1 to RA112 shown below (hereinafter referred to as Compounds of Substituent Nos. RA1 to RA112 are referred to as Inventive Compounds RA1 to RA112, and Inventive Compounds RA1 to RA112 are collectively referred to as Inventive Compound RA) can be obtained according to the method described in the above-mentioned production method it can.
Substituent numbers RA1 to RA112 represent a combination of R 21 , R 22 , R 23 , R 24 and R 25 in the compound represented by the formula (II), and Number: R 21 , R 22 , R 23 , R 24 , R 25 ].
For example, the substituent number RA4 represents a combination in which R 21 , R 22 , R 23 and R 24 are a hydrogen atom and R 25 is an isopropyl group.

例えば、本発明化合物RA4とは、式(II)で表される化合物において置換基番号がRA4である化合物を意味し、式(II)で表される化合物において、R21、R22、R23、及びR24が水素原子であり、R25がイソプロピル基である下記の化合物を表す。

Figure 2019089711
For example, the compound RA4 of the present invention means a compound having a substituent number of RA4 in the compound represented by the formula (II), and R 21 , R 22 and R 23 in the compound represented by the formula (II) And R 24 is a hydrogen atom, and R 25 is an isopropyl group.
Figure 2019089711

[置換基番号;R21,R22,R23,R24,R25]:[RA1;H,H,H,H,Me],[RA2;H,H,H,H,Et],[RA3;H,H,H,H,Pr],[RA4;H,H,H,H,i-Pr],[RA5;H,H,H,H,c-Pr],[RA6;H,H,H,H,Bu],[RA7;H,H,H,H,i-Bu],[RA8;H,H,H,H,t-Bu],[RA9;H,H,H,H,c-PrCH2],[RA10;H,H,H,H,Ph],[RA11;H,H,H,H,Bn],[RA12;H,H,H,H,CF3],[RA13;H,H,H,H,CF3CH2],[RA14;H,H,H,H,CF3CF2],[RA15;H,H,H,H,CF2H],[RA16;H,H,H,H,CF2HCH2],[RA17;F,H,H,H,Me],[RA18;F,H,H,H,Et],[RA19;F,H,H,H,Pr],[RA20;F,H,H,H,i-Pr],[RA21;F,H,H,H,c-Pr],[RA22;F,H,H,H,Bu],[RA23;F,H,H,H,i-Bu],[RA24;F,H,H,H,t-Bu],[RA25;F,H,H,H,c-PrCH2],[RA26;F,H,H,H,Ph],[RA27;F,H,H,H,Bn],[RA28;F,H,H,H,CF3],[RA29;F,H,H,H,CF3CH2],[RA30;F,H,H,H,CF3CF2],[RA31;F,H,H,H,CF2H],[RA32;F,H,H,H,CF2HCH2],[RA33;H,F,H,H,Me],[RA34;H,F,H,H,Et],[RA35;H,F,H,H,Pr],[RA36;H,F,H,H,i-Pr],[RA37;H,F,H,H,c-Pr],[RA38;H,F,H,H,Bu],[RA39;H,F,H,H,i-Bu],[RA40;H,F,H,H,t-Bu],[RA41;H,F,H,H,c-PrCH2],[RA42;H,F,H,H,Ph],[RA43;H,F,H,H,Bn],[RA44;H,F,H,H,CF3],[RA45;H,F,H,H,CF3CH2],[RA46;H,F,H,H,CF3CF2],[RA47;H,F,H,H,CF2H],[RA48;H,F,H,H,CF2HCH2],[RA49;F,F,H,H,Me],[RA50;F,F,H,H,Et],[RA51;F,F,H,H,Pr],[RA52;F,F,H,H,i-Pr],[RA53;F,F,H,H,c-Pr],[RA54;F,F,H,H,Bu],[RA55;F,F,H,H,i-Bu],[RA56;F,F,H,H,t-Bu],[RA57;F,F,H,H,c-PrCH2],[RA58;F,F,H,H,Ph],[RA59;F,F,H,H,Bn],[RA60;F,F,H,H,CF3],[RA61;F,F,H,H,CF3CH2],[RA62;F,F,H,H,CF3CF2],[RA63;F,F,H,H,CF2H],[RA64;F,F,H,H,CF2HCH2],[RA65;F,H,F,H,Me],[RA66;F,H,F,H,Et],[RA67;F,H,F,H,Pr],[RA68;F,H,F,H,i-Pr],[RA69;F,H,F,H,c-Pr],[RA70;F,H,F,H,Bu],[RA71;F,H,F,H,i-Bu],[RA72;F,H,F,H,t-Bu],[RA73;F,H,F,H,c-PrCH2],[RA74;F,H,F,H,Ph],[RA75;F,H,F,H,Bn],[RA76;F,H,F,H,CF3],[RA77;F,H,F,H,CF3CH2],[RA78;F,H,F,H,CF3CF2],[RA79;F,H,F,H,CF2H],[RA80;F,H,F,H,CF2HCH2],[RA81;F,H,H,F,Me],[RA82;F,H,H,F,Et],[RA83;F,H,H,F,Pr],[RA84;F,H,H,F,i-Pr],[RA85;F,H,H,F,c-Pr],[RA86;F,H,H,F,Bu],[RA87;F,H,H,F,i-Bu],[RA88;F,H,H,F,t-Bu],[RA89;F,H,H,F,c-PrCH2],[RA90;F,H,H,F,Ph],[RA91;F,H,H,F,Bn],[RA92;F,H,H,F,CF3],[RA93;F,H,H,F,CF3CH2],[RA94;F,H,H,F,CF3CF2],[RA95;F,H,H,F,CF2H],[RA96;F,H,H,F,CF2HCH2],[RA97;H,F,H,F,Me],[RA98;H,F,H,F,Et],[RA99;H,F,H,F,Pr],[RA100;H,F,H,F,i-Pr],[RA101;H,F,H,F,c-Pr],[RA102;H,F,H,F,Bu],[RA103;H,F,H,F,i-Bu],[RA104;H,F,H,F,t-Bu],[RA105;H,F,H,F,c-PrCH2],[RA106;H,F,H,F,Ph],[RA107;H,F,H,F,Bn],[RA108;H,F,H,F,CF3],[RA109;H,F,H,F,CF3CH2],[RA110;H,F,H,F,CF3CF2],[RA111;H,F,H,F,CF2H],[RA112;H,F,H,F,CF2HCH2] [Substituent group number; R 21, R 22, R 23, R 24, R 25]: [RA1; H, H, H, H, Me], [RA2; H, H, H, H, Et], [ RA3; H, H, H, H, Pr, [RA 4; H, H, H, H, i-Pr], [RA 5; H, H, H, H, c-Pr], [RA 6; H, H, H, H, Bu], [RA7; H, H, H, H, i, Bu], [RA 8; H, H, H, H, t, Bu], [RA 9; H, H, H, H H, c-PrCH 2], [RA10; H, H, H, H, Ph], [RA11; H, H, H, H, Bn], [RA12; H, H, H, H, CF 3] , [RA 13; H, H, H, H, CF 3 CH 2 ], [RA 14; H, H, H, H, CF 3 CF 2 ], [RA 15; H, H, H, H, CF 2 H] , [RA 16; H, H, H, H, CF 2 HCH 2 ], [RA 17; F, H, H, H, Me], [RA 18; F, H, H, H, Et], [RA 19; , H, H, H, Pr], [RA 20; F, H, H, H, i-Pr], [RA 21; F, H, H, H, c, Pr], [RA 22; F, H, H , H, Bu], [RA23; F, H, H, H, i-Bu], [RA 24; F, H, H, H, t, Bu], [RA 25; F, H, H, H, c -PrCH 2], [RA26; F , H, H, H, Ph], [RA27; F, H, H, H, Bn], [RA28; F, H, H, H, CF 3], [RA29 F, H, H, H, H, CF 3 CH 2 ], [RA 30; F, H, H, H, CF 3 CF 2 ], [RA 31; F, H, H, H, CF 2 H], [RA 32 F, H, H, H, H, CF 2 HCH 2 ], [RA 33; H, F, H, H, Me], [RA 34; H, F, H, H, Et], [RA 35; H, F, H, H, Pr], [RA 36; H, F, H, H, i-Pr], [RA 37; H, F, H, H, c-Pr], [RA 38; H, F, H, H, H Bu], [RA 39; H, F, H, H, i-Bu], [RA 40; H, F, H, H, t-Bu], [RA 41; H, F, H, H, c-PrCH 2 ], [RA42; H, F, H, H, Ph], [RA 43; H, F, H, H, Bn], [RA 44; H, F, H, H, CF 3 ], [RA 45; H, F, H, H, CF 3 CH 2 ], [RA 46; H, F, H, H, CF 3 CF 2 ], [RA 47 H, F, H, H, CF 2 H], [RA 48; H, F, H, H, CF 2 HCH 2 ], [RA 49; F, F, H, H, Me], [RA 50; F, F, H, H, Et], [RA 51; F, F, H, H, Pr], [RA 52; F, F, H, H, i-Pr], [RA 53; F, F, H, H, c-Pr], [RA 54; F, F, H, H, Bu], [RA 55; F, F, H, H, i-Bu], [RA 56; F, F, H, H, t-Bu] , [RA 57; F, F, H, H, c-PrCH 2 ], [RA 58; F, F, H, H, Ph], [RA 59; F, F, H, H, Bn], [RA 60; , F, H, H, CF 3 ], [RA 61; F, F, H, H, CF 3 CH 2 ], [RA 62; F, F, H, H, CF 3 CF 2 ], [RA 63; F, F, H, H, CF 2 H], [RA 64; F, F, H, H, CF 2 HCH 2 ], [RA 65; F, H, F, H, Me], [RA 66; F, H, F , H, Et], [RA 67; F, H, F, H, Pr], [RA 68; F, H, F, H, i-Pr], [RA 69; F, H, F, H, c-Pr ], [RA 70; F, H, F, H, Bu], [RA 71; F, H, F, H, i-Bu], [RA 72; F, H, F, H, t-Bu], [RA 73] F, H, F, H, c-PrCH 2 ], [RA 74; F, H, F, H, Ph], [RA 75; F, H, F, H, Bn], [RA 76; F, H, F, H, CF 3 ], [RA 77; F, H, F, H, CF 3 CH 2 ], [RA 78; F, H, F, H, CF 3 CF 2 ], [RA 79; F, H, F , H, CF 2 H], [RA80; F, H, F, H, CF 2 HCH 2], [RA81; F, H, H, F, Me], [RA82; F, H, H, F, Et], [RA 83; F, H, H, F, Pr], [RA 84; F, H, H, F, i-Pr], [RA 85; F, H, H, F, c-Pr], [RA RA 86; F, H, H, F, Bu], [RA 87; F, H, H, F, i-Bu], [RA 88; F, H, H, F, t-Bu], [RA 89; H, H, F, c- PrCH 2], [RA90; F, H, H, F, Ph], [RA91; F, H, H, F, Bn], [RA92; F, H, H, F , CF 3 ], [RA 93; F, H, H, F, CF 3 CH 2 ], [RA 94; F, H, H, F, CF 3 CF 2 ], [RA 95; F, H, H, F, CF 2 H], [RA 96; F, H, H, F, CF 2 HCH 2 ], [RA 97; H, F, H, F, Me], [RA 98; H, F, H, F, Et], [RA 99; H, F, H, F, Pr], [RA 100; H, F, H, F, i-Pr], [RA 101; H, F, H, F, c-Pr], [RA 102; H, F, H, F, Bu], [RA 103; H, F, H, F, i-Bu], [RA 104; H, F, H, F, t- Bu], [RA 105; H, F, H, F, c-PrCH 2 ], [RA 106; H, F, H, F, Ph], [RA 107; H, F, H, F, Bn], [RA 108 H, F, H, F, CF 3 ], [RA 109; H, F, H, F, CF 3 CH 2 ], [RA 110; H, F, H, F, CF 3 CF 2 ], [RA 111; H, F, H, F, CF 2 H], [RA 112; H, F, H, F, CF 2 HCH 2 ]

式(III)

Figure 2019089711
〔式中、R21、R22、R23、R24及びR25は上記と同じ意味を表す。〕で表される化合物において、R21、R22、R23、R24及びR25の組合わせが下記に示される置換基番号RB1〜RB112のいずれかに記載の組合わせである化合物(以下、置換基番号RB1〜RB112の化合物を本発明化合物RB1〜RB112と表し、本発明化合物RB1〜RB112をまとめて本発明化合物RBと表す)は、上記の製造法に記載の方法に準じて得ることができる。
なお、置換基番号RB1〜RB112とは、式(III)で表される化合物における、R21、R22、R23、R24及びR25の組合わせを表すものであり、以下、[置換基番号;R21,R22,R23,R24,R25]と記す。
例えば、置換基番号RB4とは、R21、R22、R23、及びR24が水素原子であり、R25がイソプロピル基である組合せを表す。 Formula (III)
Figure 2019089711
[Wherein, R 21 , R 22 , R 23 , R 24 and R 25 represent the same meaning as described above. In the compound represented by the above, a compound in which the combination of R 21 , R 22 , R 23 , R 24 and R 25 is a combination described in any of the substituent numbers RB1 to RB112 shown below (hereinafter referred to as Compounds of Substituent Nos. RB1 to RB112 are referred to as Compounds of the Invention RB1 to RB112, and Compounds RB1 to RB112 of the Invention are collectively referred to as Compound of the Invention RB) can be obtained according to the method described in the above-mentioned production method it can.
Note that the substituent number RB1~RB112, in the compound represented by the formula (III), and represents the combination of R 21, R 22, R 23 , R 24 and R 25, or less, [substituent group Number: R 21 , R 22 , R 23 , R 24 , R 25 ].
For example, the substituent number RB4 represents a combination in which R 21 , R 22 , R 23 and R 24 are a hydrogen atom and R 25 is an isopropyl group.

例えば、本発明化合物RB4とは、式(III)で表される化合物において置換基番号がRB4である化合物を意味し、式(III)で表される化合物において、R21、R22、R23、及びR24が水素原子であり、R25がイソプロピル基である下記の化合物を表す。

Figure 2019089711
For example, the compound RB4 of the present invention means a compound having a substituent number of RB4 in the compound represented by the formula (III), and R 21 , R 22 and R 23 in the compound represented by the formula (III) And R 24 is a hydrogen atom, and R 25 is an isopropyl group.
Figure 2019089711

[置換基番号;R21,R22,R23,R24,R25]:[RB1;H,H,H,H,Me],[RB2;H,H,H,H,Et],[RB3;H,H,H,H,Pr],[RB4;H,H,H,H,i-Pr],[RB5;H,H,H,H,c-Pr],[RB6;H,H,H,H,Bu],[RB7;H,H,H,H,i-Bu],[RB8;H,H,H,H,t-Bu],[RB9;H,H,H,H,c-PrCH2],[RB10;H,H,H,H,Ph],[RB11;H,H,H,H,Bn],[RB12;H,H,H,H,CF3],[RB13;H,H,H,H,CF3CH2],[RB14;H,H,H,H,CF3CF2],[RB15;H,H,H,H,CF2H],[RB16;H,H,H,H,CF2HCH2],[RB17;F,H,H,H,Me],[RB18;F,H,H,H,Et],[RB19;F,H,H,H,Pr],[RB20;F,H,H,H,i-Pr],[RB21;F,H,H,H,c-Pr],[RB22;F,H,H,H,Bu],[RB23;F,H,H,H,i-Bu],[RB24;F,H,H,H,t-Bu],[RB25;F,H,H,H,c-PrCH2],[RB26;F,H,H,H,Ph],[RB27;F,H,H,H,Bn],[RB28;F,H,H,H,CF3],[RB29;F,H,H,H,CF3CH2],[RB30;F,H,H,H,CF3CF2],[RB31;F,H,H,H,CF2H],[RB32;F,H,H,H,CF2HCH2],[RB33;H,F,H,H,Me],[RB34;H,F,H,H,Et],[RB35;H,F,H,H,Pr],[RB36;H,F,H,H,i-Pr],[RB37;H,F,H,H,c-Pr],[RB38;H,F,H,H,Bu],[RB39;H,F,H,H,i-Bu],[RB40;H,F,H,H,t-Bu],[RB41;H,F,H,H,c-PrCH2],[RB42;H,F,H,H,Ph],[RB43;H,F,H,H,Bn],[RB44;H,F,H,H,CF3],[RB45;H,F,H,H,CF3CH2],[RB46;H,F,H,H,CF3CF2],[RB47;H,F,H,H,CF2H],[RB48;H,F,H,H,CF2HCH2],[RB49;F,F,H,H,Me],[RB50;F,F,H,H,Et],[RB51;F,F,H,H,Pr],[RB52;F,F,H,H,i-Pr],[RB53;F,F,H,H,c-Pr],[RB54;F,F,H,H,Bu],[RB55;F,F,H,H,i-Bu],[RB56;F,F,H,H,t-Bu],[RB57;F,F,H,H,c-PrCH2],[RB58;F,F,H,H,Ph],[RB59;F,F,H,H,Bn],[RB60;F,F,H,H,CF3],[RB61;F,F,H,H,CF3CH2],[RB62;F,F,H,H,CF3CF2],[RB63;F,F,H,H,CF2H],[RB64;F,F,H,H,CF2HCH2],[RB65;F,H,F,H,Me],[RB66;F,H,F,H,Et],[RB67;F,H,F,H,Pr],[RB68;F,H,F,H,i-Pr],[RB69;F,H,F,H,c-Pr],[RB70;F,H,F,H,Bu],[RB71;F,H,F,H,i-Bu],[RB72;F,H,F,H,t-Bu],[RB73;F,H,F,H,c-PrCH2],[RB74;F,H,F,H,Ph],[RB75;F,H,F,H,Bn],[RB76;F,H,F,H,CF3],[RB77;F,H,F,H,CF3CH2],[RB78;F,H,F,H,CF3CF2],[RB79;F,H,F,H,CF2H],[RB80;F,H,F,H,CF2HCH2],[RB81;F,H,H,F,Me],[RB82;F,H,H,F,Et],[RB83;F,H,H,F,Pr],[RB84;F,H,H,F,i-Pr],[RB85;F,H,H,F,c-Pr],[RB86;F,H,H,F,Bu],[RB87;F,H,H,F,i-Bu],[RB88;F,H,H,F,t-Bu],[RB89;F,H,H,F,c-PrCH2],[RB90;F,H,H,F,Ph],[RB91;F,H,H,F,Bn],[RB92;F,H,H,F,CF3],[RB93;F,H,H,F,CF3CH2],[RB94;F,H,H,F,CF3CF2],[RB95;F,H,H,F,CF2H],[RB96;F,H,H,F,CF2HCH2],[RB97;H,F,H,F,Me],[RB98;H,F,H,F,Et],[RB99;H,F,H,F,Pr],[RB100;H,F,H,F,i-Pr],[RB101;H,F,H,F,c-Pr],[RB102;H,F,H,F,Bu],[RB103;H,F,H,F,i-Bu],[RB104;H,F,H,F,t-Bu],[RB105;H,F,H,F,c-PrCH2],[RB106;H,F,H,F,Ph],[RB107;H,F,H,F,Bn],[RB108;H,F,H,F,CF3],[RB109;H,F,H,F,CF3CH2],[RB110;H,F,H,F,CF3CF2],[RB111;H,F,H,F,CF2H],[RB112;H,F,H,F,CF2HCH2] [Substituent number; R 21 , R 22 , R 23 , R 24 , R 25 ]: [RB 1; H, H, H, H, Me], [RB 2; H, H, H, H, Et], [[ RB3, H, H, H, H, Pr, [RB4; H, H, H, H, i-Pr], [RB5; H, H, H, H, c-Pr], [RB6; H, H, H, H, Bu], [RB7; H, H, H, H, i, Bu], [RB 8; H, H, H, H, t, Bu], [RB 9; H, H, H, H H, c-PrCH 2], [RB10; H, H, H, H, Ph], [RB11; H, H, H, H, Bn], [RB12; H, H, H, H, CF 3] , [RB13; H, H, H, H, CF 3 CH 2 ], [RB 14; H, H, H, H, CF 3 CF 2 ], [RB 15; H, H, H, H, CF 2 H] , [RB16; H, H, H, H, CF 2 HCH 2 ], [RB 17; F, H, H, H, Me], [RB 18; F, H, H, H, Et], [RB 19; F , H, H, H, Pr], [RB 20; F, H, H, H, i-Pr], [RB 21; F, H, H, H, c, Pr], [RB 22; F, H, H] , H, Bu], [RB23; F, H, H, H, i, Bu], [RB 24; F, H, H, H, t, Bu], [RB 25; F, H, H, H, c -PrCH 2], [RB26; F , H, H, H, Ph], [RB27; F, H, H, H, Bn], [RB28; F, H, H, H, CF 3], [RB29 ; F, H, H, H , CF 3 CH 2], [RB30; F, H, H, H, CF 3 CF 2], [RB31; F, H, H, H, CF 2 H], [RB32 F, H, H, H, H, CF 2 HCH 2 ], [RB 33; H, F, H, H, Me], [RB 34; H, F, H, H, Et], [RB 35; H, F, H, H, Pr], [RB 36; H, F, H, H, i-Pr], [RB 37; H, F, H, H, c-Pr], [RB 38; H, F, H, H, H Bu], [RB 39; H, F, H, H, i-Bu], [RB 40; H, F, H, H, t-Bu], [RB 41; H, F, H, H, c-PrCH 2 ], [RB42; H, F, H, H, Ph], [RB 43; H, F, H, H, Bn], [RB 44; H, F, H, H, CF 3 ], [RB 45; H, F, H, H, CF 3 CH 2 ], [RB 46; H, F, H, H, CF 3 CF 2 ], [RB 47 H, F, H, H, CF 2 H], [RB 48; H, F, H, H, CF 2 HCH 2 ], [RB 49; F, F, H, H, Me], [RB 50; F, F, H, H, Et], [RB 51; F, F, H, H, Pr], [RB 52; F, F, H, H, i-Pr], [RB 53; F, F, H, H, c-Pr], [RB 54; F, F, H, H, Bu], [RB 55; F, F, H, H, i-Bu], [RB 56; F, F, H, H, t-Bu] , [RB 57; F, F, H, H, c, -PrCH 2 ], [RB 58; F, F, H, H, Ph], [RB 59; F, F, H, H, Bn], [RB 60; , F, H, H, CF 3 ], [RB 61; F, F, H, H, CF 3 CH 2 ], [RB 62; F, F, H, H, CF 3 CF 2 ], [RB 63; F, F, H, H, CF 2 H], [RB 64; F, F, H, H, CF 2 HCH 2 ], [RB 65; F, H, F, H, Me], [RB 66; F, H, F , H, Et], [RB67; F, H, F, H, Pr], [RB 68; F, H, F, H, i-Pr], [RB69; F, H, F, H, c-Pr ], [RB70; F, H, F, H, Bu], [RB 71; F, H, F, H, i-Bu], [RB 72; F, H, F, H, t-Bu], [RB 73] F, H, F, H, c-PrCH 2 ], [RB 74; F, H, F, H, Ph], [RB 75; F, H, F, H, Bn], [RB 76; F, H, F, H, CF 3 ], [RB 77; F, H, F, H, CF 3 CH 2 ], [RB 78; F, H, F, H, CF 3 CF 2 ], [RB 79; F, H, F , H, CF 2 H], [RB80; F, H, F, H, CF 2 HCH 2], [RB81; F, H, H, F, Me], [RB82; F, H, H, F, Et], [RB 83; F, H, H, F, Pr], [RB 84; F, H, H, F, i-Pr], [RB 85; F, H, H, F, c-Pr], [RB RB 86; F, H, H, F, Bu], [RB 87; F, H, H, F, i-Bu], [RB 88; F, H, H, F, t-Bu], [RB 89; F, H, H, F, c- PrCH 2], [RB90; F, H, H, F, Ph], [RB91; F, H, H, F, Bn], [RB92; F, H, H, F , CF 3 ], [RB 93; F, H, H, F, CF 3 CH 2 ], [RB 94; F, H, H, F, CF 3 CF 2 ], [RB95; F, H, H , F, CF 2 H], [RB96; F, H, H, F, CF 2 HCH 2], [RB97; H, F, H, F, Me], [RB98; H, F, H, F, Et], [RB99; H, F, H, F, Pr], [RB 100; H, F, H, F, i-Pr], [RB 101; H, F, H, F, c-Pr], [RB 102; H, F, H, F, Bu], [RB 103; H, F, H, F, i-Bu], [RB 104; H, F, H, F, t- Bu], [RB 105; H, F, H, F, c-PrCH 2 ], [RB 106; H, F, H, F, Ph], [RB 107; H, F, H, F, Bn], [RB 108 H, F, H, F, CF 3 ], [RB 109; H, F, H, F, CF 3 CH 2 ], [RB 110; H, F, H, F, CF 3 CF 2 ], [RB 111; H, F, H, F, CF 2 H], [RB112; H, F, H, F, CF 2 HCH 2]

式(IV)

Figure 2019089711
〔式中、R21、R22、R23、R24及びR25は上記と同じ意味を表す。〕
で表される化合物において、R21、R22、R23、R24及びR25の組合わせが下記に示される置換基番号RC1〜RC112のいずれかに記載の組合わせである化合物(以下、置換基番号RC1〜RC112の化合物を本発明化合物RC1〜RC112と表し、本発明化合物RC1〜RC112をまとめて本発明化合物RCと表す)は、上記の製造法に記載の方法に準じて得ることができる。
なお、置換基番号RC1〜RC112とは、式(IV)で表される化合物における、R21、R22、R23、R24及びR25の組合わせを表すものであり、以下、[置換基番号;R21,R22,R23,R24,R25]と記す。
例えば、置換基番号RC4とは、R21、R22、R23、及びR24が水素原子であり、R25がイソプロピル基である組合せを表す。 Formula (IV)
Figure 2019089711
[Wherein, R 21 , R 22 , R 23 , R 24 and R 25 represent the same meaning as described above. ]
Wherein the combination of R 21 , R 22 , R 23 , R 24 and R 25 is a combination as described in any of the substituent numbers RC1 to RC112 shown below (hereinafter referred to as substitution Compounds of group numbers RC1 to RC112 are referred to as compounds of the present invention RC1 to RC112, and compounds of the present invention RC1 to RC112 are collectively referred to as the compound of the present invention RC) can be obtained according to the method described in the above-mentioned production method .
In addition, the substituent numbers RC1 to RC112 represent a combination of R 21 , R 22 , R 23 , R 24 and R 25 in the compound represented by the formula (IV), and hereinafter, [Substituent Number: R 21 , R 22 , R 23 , R 24 , R 25 ].
For example, the substituent number RC4 represents a combination in which R 21 , R 22 , R 23 and R 24 are a hydrogen atom and R 25 is an isopropyl group.

例えば、本発明化合物RC4とは、式(IV)で表される化合物において置換基番号がRC4である化合物を意味し、式(IV)で表される化合物において、R21、R22、R23、及びR24が水素原子であり、R25がイソプロピル基である下記の化合物を表す。

Figure 2019089711
For example, the compound RC4 of the present invention means a compound having a substituent number of RC4 in the compound represented by the formula (IV), and R 21 , R 22 and R 23 in the compound represented by the formula (IV) And R 24 is a hydrogen atom, and R 25 is an isopropyl group.
Figure 2019089711

[置換基番号;R21,R22,R23,R24,R25]:[RC1;H,H,H,H,Me],[RC2;H,H,H,H,Et],[RC3;H,H,H,H,Pr],[RC4;H,H,H,H,i-Pr],[RC5;H,H,H,H,c-Pr],[RC6;H,H,H,H,Bu],[RC7;H,H,H,H,i-Bu],[RC8;H,H,H,H,t-Bu],[RC9;H,H,H,H,c-PrCH2],[RC10;H,H,H,H,Ph],[RC11;H,H,H,H,Bn],[RC12;H,H,H,H,CF3],[RC13;H,H,H,H,CF3CH2],[RC14;H,H,H,H,CF3CF2],[RC15;H,H,H,H,CF2H],[RC16;H,H,H,H,CF2HCH2],[RC17;F,H,H,H,Me],[RC18;F,H,H,H,Et],[RC19;F,H,H,H,Pr],[RC20;F,H,H,H,i-Pr],[RC21;F,H,H,H,c-Pr],[RC22;F,H,H,H,Bu],[RC23;F,H,H,H,i-Bu],[RC24;F,H,H,H,t-Bu],[RC25;F,H,H,H,c-PrCH2],[RC26;F,H,H,H,Ph],[RC27;F,H,H,H,Bn],[RC28;F,H,H,H,CF3],[RC29;F,H,H,H,CF3CH2],[RC30;F,H,H,H,CF3CF2],[RC31;F,H,H,H,CF2H],[RC32;F,H,H,H,CF2HCH2],[RC33;H,F,H,H,Me],[RC34;H,F,H,H,Et],[RC35;H,F,H,H,Pr],[RC36;H,F,H,H,i-Pr],[RC37;H,F,H,H,c-Pr],[RC38;H,F,H,H,Bu],[RC39;H,F,H,H,i-Bu],[RC40;H,F,H,H,t-Bu],[RC41;H,F,H,H,c-PrCH2],[RC42;H,F,H,H,Ph],[RC43;H,F,H,H,Bn],[RC44;H,F,H,H,CF3],[RC45;H,F,H,H,CF3CH2],[RC46;H,F,H,H,CF3CF2],[RC47;H,F,H,H,CF2H],[RC48;H,F,H,H,CF2HCH2],[RC49;F,F,H,H,Me],[RC50;F,F,H,H,Et],[RC51;F,F,H,H,Pr],[RC52;F,F,H,H,i-Pr],[RC53;F,F,H,H,c-Pr],[RC54;F,F,H,H,Bu],[RC55;F,F,H,H,i-Bu],[RC56;F,F,H,H,t-Bu],[RC57;F,F,H,H,c-PrCH2],[RC58;F,F,H,H,Ph],[RC59;F,F,H,H,Bn],[RC60;F,F,H,H,CF3],[RC61;F,F,H,H,CF3CH2],[RC62;F,F,H,H,CF3CF2],[RC63;F,F,H,H,CF2H],[RC64;F,F,H,H,CF2HCH2],[RC65;F,H,F,H,Me],[RC66;F,H,F,H,Et],[RC67;F,H,F,H,Pr],[RC68;F,H,F,H,i-Pr],[RC69;F,H,F,H,c-Pr],[RC70;F,H,F,H,Bu],[RC71;F,H,F,H,i-Bu],[RC72;F,H,F,H,t-Bu],[RC73;F,H,F,H,c-PrCH2],[RC74;F,H,F,H,Ph],[RC75;F,H,F,H,Bn],[RC76;F,H,F,H,CF3],[RC77;F,H,F,H,CF3CH2],[RC78;F,H,F,H,CF3CF2],[RC79;F,H,F,H,CF2H],[RC80;F,H,F,H,CF2HCH2],[RC81;F,H,H,F,Me],[RC82;F,H,H,F,Et],[RC83;F,H,H,F,Pr],[RC84;F,H,H,F,i-Pr],[RC85;F,H,H,F,c-Pr],[RC86;F,H,H,F,Bu],[RC87;F,H,H,F,i-Bu],[RC88;F,H,H,F,t-Bu],[RC89;F,H,H,F,c-PrCH2],[RC90;F,H,H,F,Ph],[RC91;F,H,H,F,Bn],[RC92;F,H,H,F,CF3],[RC93;F,H,H,F,CF3CH2],[RC94;F,H,H,F,CF3CF2],[RC95;F,H,H,F,CF2H],[RC96;F,H,H,F,CF2HCH2],[RC97;H,F,H,F,Me],[RC98;H,F,H,F,Et],[RC99;H,F,H,F,Pr],[RC100;H,F,H,F,i-Pr],[RC101;H,F,H,F,c-Pr],[RC102;H,F,H,F,Bu],[RC103;H,F,H,F,i-Bu],[RC104;H,F,H,F,t-Bu],[RC105;H,F,H,F,c-PrCH2],[RC106;H,F,H,F,Ph],[RC107;H,F,H,F,Bn],[RC108;H,F,H,F,CF3],[RC109;H,F,H,F,CF3CH2],[RC110;H,F,H,F,CF3CF2],[RC111;H,F,H,F,CF2H],[RC112;H,F,H,F,CF2HCH2] [Substituent number; R 21 , R 22 , R 23 , R 24 , R 25 ]: [RC1; H, H, H, H, Me], [RC 2; H, H, H, H, Et], [[ RC3, H, H, H, H, Pr, [RC 4; H, H, H, H, i-Pr], [RC 5; H, H, H, H, c-Pr], [RC 6; H, H, H, H, Bu], [RC7; H, H, H, H, i, Bu], [RC 8; H, H, H, H, t, Bu], [RC 9; H, H, H, H, c-PrCH 2], [RC10; H, H, H, H, Ph], [RC11; H, H, H, H, Bn], [RC12; H, H, H, H, CF 3] , [RC13; H, H, H, H, CF 3 CH 2 ], [RC 14; H, H, H, H, CF 3 CF 2 ], [RC 15; H, H, H, H, CF 2 H] , [RC16; H, H, H, H, CF 2 HCH 2 ], [RC 17; F, H, H, H, Me], [RC 18; F, H, H, H, Et], [RC 19; , H, H, H, Pr], [RC 20; F, H, H, H, i-Pr], [RC 21; F, H, H, H, c, Pr], [RC 22; F, H, H , H, Bu], [RC23; F, H, H, H, i-Bu], [RC 24; F, H, H, H, t-Bu], [RC 25; F, H, H, H, c -PrCH 2], [RC26; F , H, H, H, Ph], [RC27; F, H, H, H, Bn], [RC28; F, H, H, H, CF 3], [RC29 F, H, H, H, H, CF 3 CH 2 ], [RC 30; F, H, H, H, CF 3 CF 2 ], [RC 31; F, H, H, H, CF 2 H], [RC 32 F, H, H, H, H, CF 2 HCH 2 ], [RC 33; H, F, H, H, Me], [RC 34; H, F, H, H, Et], [RC 35; H, F, H, H, Pr], [RC 36; H, F, H, H, i-Pr], [RC 37; H, F, H, H, c-Pr], [RC 38; H, F, H, H, H Bu], [RC 39; H, F, H, H, i-Bu], [RC 40; H, F, H, H, t-Bu], [RC 41; H, F, H, H, c-PrCH 2 H, F, H, H, Ph], [RC 43; H, F, H, H, Bn], [RC 44; H, F, H, H, CF 3 ], [RC 45; H, F, H, H, CF 3 CH 2 ], [RC 46; H, F, H, H, CF 3 CF 2 ], [RC 47 H, F, H, H, CF 2 H], [RC 48; H, F, H, H, CF 2 HCH 2 ], [RC 49; F, F, H, H, Me], [RC 50; F, F, H, H, Et], [RC 51; F, F, H, H, Pr], [RC 52; F, F, H, H, i-Pr], [RC 53; F, F, H, H, c-Pr], [RC 54; F, F, H, H, Bu], [RC 55; F, F, H, H, i-Bu], [RC 56; F, F, H, H, t-Bu] , [RC 57; F, F, H, H, c-PrCH 2 ], [RC 58; F, F, H, H, Ph], [RC 59; F, F, H, H, Bn], [RC 60; , F, H, H, CF 3 ], [RC 61; F, F, H, H, CF 3 CH 2 ], [RC 62; F, F, H, H, CF 3 CF 2 ], [RC 63; F, F, H, H, CF 2 H], [RC 64; F, F, H, H, CF 2 HCH 2 ], [RC 65; F, H, F, H, Me], [RC 66; F, H, F , H, Et], [RC 67; F, H, F, H, Pr], [RC 68; F, H, F, H, i-Pr], [RC 69; F, H, F, H, c-Pr ], [RC 70; F, H, F, H, Bu], [RC 71; F, H, F, H, i-Bu], [RC 72; F, H, F, H, t-Bu], [RC 73] F, H, F, H, c-PrCH 2 ], [RC 74; F, H, F, H, Ph], [RC 75; F, H, F, H, Bn], [RC 76; F, H, F, H, CF 3 ], [RC 77; F, H, F, H, CF 3 CH 2 ], [RC 78; F, H, F, H, CF 3 CF 2 ], [RC 79; F, H, F , H, CF 2 H], [RC80; F, H, F, H, CF 2 HCH 2], [RC81; F, H, H, F, Me], [RC82; F, H, H, F, Et], [RC 83; F, H, H, F, Pr], [RC 84; F, H, H, F, i-Pr], [RC 85; F, H, H, F, c-Pr], [RC RC86; F, H, H, F, Bu], [RC 87; F, H, H, F, i-Bu], [RC 88; F, H, H, F, t-Bu], [RC 89; F, H, H, F, c- PrCH 2], [RC90; F, H, H, F, Ph], [RC91; F, H, H, F, Bn], [RC92; F, H, H, F , CF 3 ], [RC 93; F, H, H, F, CF 3 CH 2 ], [RC 94; F, H, H, F, CF 3 CF 2 ], [RC 95; F, H, H, F, CF 2 H], [RC 96; F, H, H, F, CF 2 HCH 2 ], [RC 97; H, F, H, F, Me], [RC 98; H, F, H, F, Et], [RC 99; H, F, H, F, Pr], [RC 100; H, F, H, F, i-Pr], [RC 101; H, F, H, F, c-Pr], [RC 102; H, F, H, F, Bu], [RC 103; H, F, H, F, i-Bu], [RC 104; H, F, H, F, t- Bu], [RC 105; H, F, H, F, c-PrCH 2 ], [RC 106; H, F, H, F, Ph], [RC 107; H, F, H, F, Bn], [RC 108 H, F, H, F, CF 3 ], [RC 109; H, F, H, F, CF 3 CH 2 ], [RC 110; H, F, H, F, CF 3 CF 2 ], [RC 111; H, F, H, F, CF 2 H], [RC 112; H, F, H, F, CF 2 HCH 2 ]

式(V)

Figure 2019089711
〔式中、R21、R22、R23、R24及びR25は上記と同じ意味を表す。〕
で表される化合物において、R21、R22、R23、R24及びR25の組合わせが下記に示される置換基番号RD1〜RD112のいずれかに記載の組合わせである化合物(以下、置換基番号RD1〜RD112の化合物を本発明化合物RD1〜RD112と表し、本発明化合物RD1〜RD112をまとめて本発明化合物RDと表す)は、上記の製造法に記載の方法に準じて得ることができる。
なお、置換基番号RD1〜RD112とは、式(V)で表される化合物における、R21、R22、R23、R24及びR25の組合わせを表すものであり、以下、[置換基番号;R21,R22,R23,R24,R25]と記す。
例えば、置換基番号RD4とは、R21、R22、R23、及びR24が水素原子であり、R25がイソプロピル基である組合せを表す。 Formula (V)
Figure 2019089711
[Wherein, R 21 , R 22 , R 23 , R 24 and R 25 represent the same meaning as described above. ]
Wherein the combination of R 21 , R 22 , R 23 , R 24 and R 25 is a combination as set forth in any of Substituent Nos. RD1 to RD112 shown below (hereinafter referred to as substitution Compounds of group numbers RD1 to RD112 are represented as compounds of the present invention RD1 to RD112, and compounds of the present invention RD1 to RD112 are collectively represented as the compound of the present invention RD) can be obtained according to the method described in the above-mentioned production method .
Note that the substituent number RD1~RD112, in the compound represented by formula (V), and represents the combination of R 21, R 22, R 23 , R 24 and R 25, or less, [substituent group Number: R 21 , R 22 , R 23 , R 24 , R 25 ].
For example, the substituent number RD4 represents a combination in which R 21 , R 22 , R 23 and R 24 are a hydrogen atom and R 25 is an isopropyl group.

例えば、本発明化合物RD4とは置換基番号がRD4である化合物を意味し、式(V)で表される化合物において、R21、R22、R23、及びR24が水素原子であり、R25がイソプロピル基である下記の化合物を表す。

Figure 2019089711
For example, the compound RD4 of the present invention means a compound in which the substituent number is RD4, and in the compound represented by the formula (V), R 21 , R 22 , R 23 and R 24 are a hydrogen atom, R 25 represents the following compound in which an isopropyl group is present.
Figure 2019089711

[置換基番号;R21,R22,R23,R24,R25]:[RD1;H,H,H,H,Me],[RD2;H,H,H,H,Et],[RD3;H,H,H,H,Pr],[RD4;H,H,H,H,i-Pr],[RD5;H,H,H,H,c-Pr],[RD6;H,H,H,H,Bu],[RD7;H,H,H,H,i-Bu],[RD8;H,H,H,H,t-Bu],[RD9;H,H,H,H,c-PrCH2],[RD10;H,H,H,H,Ph],[RD11;H,H,H,H,Bn],[RD12;H,H,H,H,CF3],[RD13;H,H,H,H,CF3CH2],[RD14;H,H,H,H,CF3CF2],[RD15;H,H,H,H,CF2H],[RD16;H,H,H,H,CF2HCH2],[RD17;F,H,H,H,Me],[RD18;F,H,H,H,Et],[RD19;F,H,H,H,Pr],[RD20;F,H,H,H,i-Pr],[RD21;F,H,H,H,c-Pr],[RD22;F,H,H,H,Bu],[RD23;F,H,H,H,i-Bu],[RD24;F,H,H,H,t-Bu],[RD25;F,H,H,H,c-PrCH2],[RD26;F,H,H,H,Ph],[RD27;F,H,H,H,Bn],[RD28;F,H,H,H,CF3],[RD29;F,H,H,H,CF3CH2],[RD30;F,H,H,H,CF3CF2],[RD31;F,H,H,H,CF2H],[RD32;F,H,H,H,CF2HCH2],[RD33;H,F,H,H,Me],[RD34;H,F,H,H,Et],[RD35;H,F,H,H,Pr],[RD36;H,F,H,H,i-Pr],[RD37;H,F,H,H,c-Pr],[RD38;H,F,H,H,Bu],[RD39;H,F,H,H,i-Bu],[RD40;H,F,H,H,t-Bu],[RD41;H,F,H,H,c-PrCH2],[RD42;H,F,H,H,Ph],[RD43;H,F,H,H,Bn],[RD44;H,F,H,H,CF3],[RD45;H,F,H,H,CF3CH2],[RD46;H,F,H,H,CF3CF2],[RD47;H,F,H,H,CF2H],[RD48;H,F,H,H,CF2HCH2],[RD49;F,F,H,H,Me],[RD50;F,F,H,H,Et],[RD51;F,F,H,H,Pr],[RD52;F,F,H,H,i-Pr],[RD53;F,F,H,H,c-Pr],[RD54;F,F,H,H,Bu],[RD55;F,F,H,H,i-Bu],[RD56;F,F,H,H,t-Bu],[RD57;F,F,H,H,c-PrCH2],[RD58;F,F,H,H,Ph],[RD59;F,F,H,H,Bn],[RD60;F,F,H,H,CF3],[RD61;F,F,H,H,CF3CH2],[RD62;F,F,H,H,CF3CF2],[RD63;F,F,H,H,CF2H],[RD64;F,F,H,H,CF2HCH2],[RD65;F,H,F,H,Me],[RD66;F,H,F,H,Et],[RD67;F,H,F,H,Pr],[RD68;F,H,F,H,i-Pr],[RD69;F,H,F,H,c-Pr],[RD70;F,H,F,H,Bu],[RD71;F,H,F,H,i-Bu],[RD72;F,H,F,H,t-Bu],[RD73;F,H,F,H,c-PrCH2],[RD74;F,H,F,H,Ph],[RD75;F,H,F,H,Bn],[RD76;F,H,F,H,CF3],[RD77;F,H,F,H,CF3CH2],[RD78;F,H,F,H,CF3CF2],[RD79;F,H,F,H,CF2H],[RD80;F,H,F,H,CF2HCH2],[RD81;F,H,H,F,Me],[RD82;F,H,H,F,Et],[RD83;F,H,H,F,Pr],[RD84;F,H,H,F,i-Pr],[RD85;F,H,H,F,c-Pr],[RD86;F,H,H,F,Bu],[RD87;F,H,H,F,i-Bu],[RD88;F,H,H,F,t-Bu],[RD89;F,H,H,F,c-PrCH2],[RD90;F,H,H,F,Ph],[RD91;F,H,H,F,Bn],[RD92;F,H,H,F,CF3],[RD93;F,H,H,F,CF3CH2],[RD94;F,H,H,F,CF3CF2],[RD95;F,H,H,F,CF2H],[RD96;F,H,H,F,CF2HCH2],[RD97;H,F,H,F,Me],[RD98;H,F,H,F,Et],[RD99;H,F,H,F,Pr],[RD100;H,F,H,F,i-Pr],[RD101;H,F,H,F,c-Pr],[RD102;H,F,H,F,Bu],[RD103;H,F,H,F,i-Bu],[RD104;H,F,H,F,t-Bu],[RD105;H,F,H,F,c-PrCH2],[RD106;H,F,H,F,Ph],[RD107;H,F,H,F,Bn],[RD108;H,F,H,F,CF3],[RD109;H,F,H,F,CF3CH2],[RD110;H,F,H,F,CF3CF2],[RD111;H,F,H,F,CF2H],[RD112;H,F,H,F,CF2HCH2] [Substituent number; R 21 , R 22 , R 23 , R 24 , R 25 ]: [RD 1; H, H, H, H, Me], [RD 2; H, H, H, H, Et], [[ RD3, H, H, H, H, H, Pr], [RD4; H, H, H, H, i, Pr], [RD5; H, H, H, H, c, Pr], [RD 6; H, H, H, H, Bu], [RD7; H, H, H, H, i, Bu], [RD 8; H, H, H, H, t, Bu], [RD 9; H, H, H, H H, c-PrCH 2], [RD10; H, H, H, H, Ph], [RD11; H, H, H, H, Bn], [RD12; H, H, H, H, CF 3] , [RD13; H, H, H, H, CF 3 CH 2 ], [RD 14; H, H, H, H, CF 3 CF 2 ], [RD 15; H, H, H, H, CF 2 H] , [RD16; H, H, H, H, CF 2 HCH 2 ], [RD 17; F, H, H, H, Me], [RD 18; F, H, H, H, Et], [RD 19; F , H, H, H, Pr], [RD 20; F, H, H, H, i-Pr], [RD 21; F, H, H, H, c, Pr], [RD 22; F, H, H , H, Bu], [RD23; F, H, H, H, i, Bu], [RD 24; F, H, H, H, t, Bu], [RD 25; F, H, H, H, c -PrCH 2], [RD26; F , H, H, H, Ph], [RD27; F, H, H, H, Bn], [RD28; F, H, H, H, CF 3], [RD29 ; F, H, H, H , CF 3 CH 2], [RD30; F, H, H, H, CF 3 CF 2], [RD31; F, H, H, H, CF 2 H], [RD32 F, H, H, H, H, CF 2 HCH 2 ], [RD 33; H, F, H, H, Me], [RD 34; H, F, H, H, Et], [RD 35; H, F, H, H, Pr], [RD 36; H, F, H, H, i-Pr], [RD 37; H, F, H, H, c-Pr], [RD 38; H, F, H, H, H Bu], [RD 39; H, F, H, H, i-Bu], [RD 40; H, F, H, H, t-Bu], [RD 41; H, F, H, H, c-PrCH 2 ], [RD 42; H, F, H, H, Ph], [RD 43; H, F, H, H, Bn], [RD 44; H, F, H, H, CF 3 ], [RD 45; H, F, H, H, CF 3 CH 2 ], [RD 46; H, F, H, H, CF 3 CF 2 ], [RD 47 H, F, H, H, CF 2 H], [RD 48; H, F, H, H, CF 2 HCH 2 ], [RD 49; F, F, H, H, Me], [RD 50; F, F, H, H, Et], [RD 51; F, F, H, H, Pr], [RD 52; F, F, H, H, i-Pr], [RD 53; F, F, H, H, c-Pr], [RD 54; F, F, H, H, Bu], [RD 55; F, F, H, H, i-Bu], [RD 56; F, F, H, H, t-Bu] , [RD57; F, F, H, H, c-PrCH 2], [RD58; F, F, H, H, Ph], [RD59; F, F, H, H, Bn], [RD60; F , F, H, H, CF 3 ], [RD 61; F, F, H, H, CF 3 CH 2 ], [RD 62; F, F, H, H, CF 3 CF 2 ], [RD 63; F, F, H, H, CF 2 H], [RD 64; F, F, H, H, CF 2 HCH 2 ], [RD 65; F, H, F, H, Me], [RD 66; F, H, F , H, Et], [RD 67; F, H, F, H, Pr], [RD 68; F, H, F, H, i-Pr], [RD 69; F, H, F, H, c-Pr ], [RD 70; F, H, F, H, Bu], [RD 71; F, H, F, H, i-Bu], [RD 72; F, H, F, H, t-Bu], [RD 73] F, H, F, H, c-PrCH 2 ], [RD 74; F, H, F, H, Ph], [RD 75; F, H, F, H, Bn], [RD 76; F, H, F, H, CF 3 ], [RD 77; F, H, F, H, CF 3 CH 2 ], [RD 78; F, H, F, H, CF 3 CF 2 ], [RD 79; F, H, F , H, CF 2 H], [RD80; F, H, F, H, CF 2 HCH 2], [RD81; F, H, H, F, Me], [RD82; F, H, H, F, Et], [RD 83; F, H, H, F, Pr], [RD 84; F, H, H, F, i-Pr], [RD 85; F, H, H, F, c-Pr], [[ RD 86; F, H, H, F, Bu], [RD 87; F, H, H, F, i-Bu], [RD 88; F, H, H, F, t-Bu], [RD 89; F, H, H, F, c- PrCH 2], [RD90; F, H, H, F, Ph], [RD91; F, H, H, F, Bn], [RD92; F, H, H, F , CF 3 ], [RD 93; F, H, H, F, CF 3 CH 2 ], [RD 94; F, H, H, F, CF 3 CF 2 ], [RD 95; F, H, H, F, CF 2 H], [RD 96; F, H, H, F, CF 2 HCH 2 ], [RD 97; H, F, H, F, Me], [RD 98; H, F, H, F, Et, [RD 99; H, F, H, F, Pr], [RD 100; H, F, H, F, i-Pr], [RD 101; H, F, H, F, c-Pr], [RD 102; H, F, H, F, Bu], [RD 103; H, F, H, F, i-Bu], [RD 104; H, F, H, F, t- Bu], [RD 105; H, F, H, F, c-PrCH 2 ], [RD 106; H, F, H, F, Ph], [RD 107; H, F, H, F, Bn], [RD 108 H, F, H, F, CF 3 ], [RD 109; H, F, H, F, CF 3 CH 2 ], [RD 110; H, F, H, F, CF 3 CF 2 ], [RD 111; H, F, H, F, CF 2 H], [RD 112; H, F, H, F, CF 2 HCH 2 ]

式(VI)

Figure 2019089711
〔式中、R21、R22、R23、R24及びR25は上記と同じ意味を表す。〕
で表される化合物において、R21、R22、R23、R24及びR25の組合わせが下記に示される置換基番号RE1〜RE112のいずれかに記載の組合わせである化合物(以下、置換基番号RE1〜RE112の化合物を本発明化合物RE1〜RE112と表し、本発明化合物RE1〜RE112をまとめて本発明化合物REと表す)は、上記の製造法に記載の方法に準じて得ることができる。
なお、置換基番号RE1〜RE112とは、式(VI)で表される化合物における、R21、R22、R23、R24及びR25の組合わせを表すものであり、以下、[置換基番号;R21,R22,R23,R24,R25]と記す。
例えば、置換基番号RE4とは、R21、R22、R23、及びR24が水素原子であり、R25がイソプロピル基である組合せを表す。 Formula (VI)
Figure 2019089711
[Wherein, R 21 , R 22 , R 23 , R 24 and R 25 represent the same meaning as described above. ]
In the compound represented by the above, a compound in which the combination of R 21 , R 22 , R 23 , R 24 and R 25 is a combination as described in any of the substituent numbers RE1 to RE112 shown below (hereinafter referred to as substitution The compounds of group numbers RE1 to RE112 are referred to as present compounds RE1 to RE112, and the present compounds RE1 to RE112 are collectively referred to as the present compound RE)) can be obtained according to the method described in the above-mentioned production method .
In addition, Substituent Nos. RE1 to RE112 represent a combination of R 21 , R 22 , R 23 , R 24 and R 25 in the compound represented by Formula (VI), and the [Substituent Number: R 21 , R 22 , R 23 , R 24 , R 25 ].
For example, the substituent number RE4 represents a combination in which R 21 , R 22 , R 23 and R 24 are a hydrogen atom and R 25 is an isopropyl group.

例えば、本発明化合物RE4とは、式(VI)で表される化合物において置換基番号がRE4である化合物を意味し、式(VI)で表される化合物において、R21、R22、R23、及びR24が水素原子であり、R25がイソプロピル基である下記の化合物を表す。

Figure 2019089711
For example, the compound RE4 of the present invention means a compound having a substituent number of RE4 in the compound represented by the formula (VI), and R 21 , R 22 and R 23 in the compound represented by the formula (VI) And R 24 is a hydrogen atom, and R 25 is an isopropyl group.
Figure 2019089711

[置換基番号;R21,R22,R23,R24,R25]:[RE1;H,H,H,H,Me],[RE2;H,H,H,H,Et],[RE3;H,H,H,H,Pr],[RE4;H,H,H,H,i-Pr],[RE5;H,H,H,H,c-Pr],[RE6;H,H,H,H,Bu],[RE7;H,H,H,H,i-Bu],[RE8;H,H,H,H,t-Bu],[RE9;H,H,H,H,c-PrCH2],[RE10;H,H,H,H,Ph],[RE11;H,H,H,H,Bn],[RE12;H,H,H,H,CF3],[RE13;H,H,H,H,CF3CH2],[RE14;H,H,H,H,CF3CF2],[RE15;H,H,H,H,CF2H],[RE16;H,H,H,H,CF2HCH2],[RE17;F,H,H,H,Me],[RE18;F,H,H,H,Et],[RE19;F,H,H,H,Pr],[RE20;F,H,H,H,i-Pr],[RE21;F,H,H,H,c-Pr],[RE22;F,H,H,H,Bu],[RE23;F,H,H,H,i-Bu],[RE24;F,H,H,H,t-Bu],[RE25;F,H,H,H,c-PrCH2],[RE26;F,H,H,H,Ph],[RE27;F,H,H,H,Bn],[RE28;F,H,H,H,CF3],[RE29;F,H,H,H,CF3CH2],[RE30;F,H,H,H,CF3CF2],[RE31;F,H,H,H,CF2H],[RE32;F,H,H,H,CF2HCH2],[RE33;H,F,H,H,Me],[RE34;H,F,H,H,Et],[RE35;H,F,H,H,Pr],[RE36;H,F,H,H,i-Pr],[RE37;H,F,H,H,c-Pr],[RE38;H,F,H,H,Bu],[RE39;H,F,H,H,i-Bu],[RE40;H,F,H,H,t-Bu],[RE41;H,F,H,H,c-PrCH2],[RE42;H,F,H,H,Ph],[RE43;H,F,H,H,Bn],[RE44;H,F,H,H,CF3],[RE45;H,F,H,H,CF3CH2],[RE46;H,F,H,H,CF3CF2],[RE47;H,F,H,H,CF2H],[RE48;H,F,H,H,CF2HCH2],[RE49;F,F,H,H,Me],[RE50;F,F,H,H,Et],[RE51;F,F,H,H,Pr],[RE52;F,F,H,H,i-Pr],[RE53;F,F,H,H,c-Pr],[RE54;F,F,H,H,Bu],[RE55;F,F,H,H,i-Bu],[RE56;F,F,H,H,t-Bu],[RE57;F,F,H,H,c-PrCH2],[RE58;F,F,H,H,Ph],[RE59;F,F,H,H,Bn],[RE60;F,F,H,H,CF3],[RE61;F,F,H,H,CF3CH2],[RE62;F,F,H,H,CF3CF2],[RE63;F,F,H,H,CF2H],[RE64;F,F,H,H,CF2HCH2],[RE65;F,H,F,H,Me],[RE66;F,H,F,H,Et],[RE67;F,H,F,H,Pr],[RE68;F,H,F,H,i-Pr],[RE69;F,H,F,H,c-Pr],[RE70;F,H,F,H,Bu],[RE71;F,H,F,H,i-Bu],[RE72;F,H,F,H,t-Bu],[RE73;F,H,F,H,c-PrCH2],[RE74;F,H,F,H,Ph],[RE75;F,H,F,H,Bn],[RE76;F,H,F,H,CF3],[RE77;F,H,F,H,CF3CH2],[RE78;F,H,F,H,CF3CF2],[RE79;F,H,F,H,CF2H],[RE80;F,H,F,H,CF2HCH2],[RE81;F,H,H,F,Me],[RE82;F,H,H,F,Et],[RE83;F,H,H,F,Pr],[RE84;F,H,H,F,i-Pr],[RE85;F,H,H,F,c-Pr],[RE86;F,H,H,F,Bu],[RE87;F,H,H,F,i-Bu],[RE88;F,H,H,F,t-Bu],[RE89;F,H,H,F,c-PrCH2],[RE90;F,H,H,F,Ph],[RE91;F,H,H,F,Bn],[RE92;F,H,H,F,CF3],[RE93;F,H,H,F,CF3CH2],[RE94;F,H,H,F,CF3CF2],[RE95;F,H,H,F,CF2H],[RE96;F,H,H,F,CF2HCH2],[RE97;H,F,H,F,Me],[RE98;H,F,H,F,Et],[RE99;H,F,H,F,Pr],[RE100;H,F,H,F,i-Pr],[RE101;H,F,H,F,c-Pr],[RE102;H,F,H,F,Bu],[RE103;H,F,H,F,i-Bu],[RE104;H,F,H,F,t-Bu],[RE105;H,F,H,F,c-PrCH2],[RE106;H,F,H,F,Ph],[RE107;H,F,H,F,Bn],[RE108;H,F,H,F,CF3],[RE109;H,F,H,F,CF3CH2],[RE110;H,F,H,F,CF3CF2],[RE111;H,F,H,F,CF2H],[RE112;H,F,H,F,CF2HCH2] [Substituent number; R 21 , R 22 , R 23 , R 24 , R 25 ]: [RE 1; H, H, H, H, Me], [RE 2; H, H, H, H, Et], [[ RE3, H, H, H, H, Pr, [RE 4; H, H, H, H, i-Pr], [RE 5; H, H, H, H, c-Pr], [RE 6; H, H, H, H, Bu], [RE7; H, H, H, H, i, Bu], [RE 8; H, H, H, H, t, Bu], [RE 9; H, H, H, H, c-PrCH 2 ], [RE 10; H, H, H, H, Ph, [RE 11; H, H, H, H, Bn], [RE 12; H, H, H, H, CF 3 ] , [RE13; H, H, H, H, CF 3 CH 2 ], [RE 14; H, H, H, H, CF 3 CF 2 ], [RE 15; H, H, H, H, CF 2 H] , [RE16; H, H, H, H, CF 2 HCH 2 ], [RE 17; F, H, H, H, Me], [RE 18; F, H, H, H, Et], [RE 19; F , H, H, H, Pr], [RE 20; F, H, H, H, i-Pr], [RE 21; F, H, H, H, c, Pr], [RE 22; F, H, H , H, Bu], [RE23; F, H, H, H, i-Bu], [RE 24; F, H, H, H, t-Bu], [RE 25; F, H, H, H, c -PrCH 2 ], [RE26; F, H, H, H, Ph, [RE 27; F, H, H, H, Bn], [RE 28; F, H, H, H, CF 3 ], [RE 29 ; F, H, H, H , CF 3 CH 2], [RE30; F, H, H, H, CF 3 CF 2], [RE31; F, H, H, H, CF 2 H], [RE32 F, H, H, H, H, CF 2 HCH 2 ], [RE 33; H, F, H, H, Me], [RE 34; H, F, H, H, Et], [RE 35; H, F, H, H, Pr], [RE36; H, F, H, H, i-Pr], [RE 37; H, F, H, H, c-Pr], [RE 38; H, F, H, H, H, Bu], [RE 39; H, F, H, H, i-Bu], [RE 40; H, F, H, H, t-Bu], [RE 41; H, F, H, H, c-PrCH 2 ], [RE 42; H, F, H, H, Ph], [RE 43; H, F, H, H, Bn], [RE 44; H, F, H, H, CF 3 ], [RE 45; H, F, H, H, CF 3 CH 2 ], [RE 46; H, F, H, H, CF 3 CF 2 ], [RE 47 H, F, H, H, CF 2 H], [RE 48; H, F, H, H, CF 2 HCH 2 ], [RE 49; F, F, H, H, Me], [RE 50; F, F, H, H, Et], [RE 51; F, F, H, H, Pr], [RE 52; F, F, H, H, i-Pr], [RE 53; F, F, H, H, c-Pr], [RE 54; F, F, H, H, Bu], [RE 55; F, F, H, H, i-Bu], [RE 56; F, F, H, H, t-Bu] , [RE 57; F, F, H, H, c-PrCH 2 ], [RE 58; F, F, H, H, Ph], [RE 59; F, F, H, H, Bn], [RE 60; F , F, H, H, CF 3 ], [RE 61; F, F, H, H, CF 3 CH 2 ], [RE 62; F, F, H, H, CF 3 CF 2 ], [RE 63; F, F, H, H, CF 2 H], [RE 64; F, F, H, H, CF 2 HCH 2 ], [RE 65; F, H, F, H, Me], [RE 66; F, H, F , H, Et], [RE 67; F, H, F, H, Pr], [RE 68; F, H, F, H, i-Pr], [RE 69; F, H, F, H, c-Pr ], [RE 70; F, H, F, H, Bu], [RE 71; F, H, F, H, i-Bu], [RE 72; F, H, F, H, t-Bu], [RE 73 F, H, F, H, c-PrCH 2 ], [RE 74; F, H, F, H, Ph], [RE 75; F, H, F, H, Bn], [RE 76; F, H, F, H, CF 3 ], [RE 77; F, H, F, H, CF 3 CH 2 ], [RE 78; F, H, F, H, CF 3 CF 2 ], [RE 79; F, H, F , H, CF 2 H], [RE80; F, H, F, H, CF 2 HCH 2], [RE81; F, H, H, F, Me], [RE82; F, H, H, F, Et], [RE 83; F, H, H, F, Pr], [RE 84; F, H, H, F, i-Pr], [RE 85; F, H, H, F, c-Pr], [RE RE 86; F, H, H, F, Bu], [RE 87; F, H, H, F, i-Bu], [RE 88; F, H, H, F, t-Bu], [RE 89; F, H, H, F, c- PrCH 2], [RE90; F, H, H, F, Ph], [RE91; F, H, H, F, Bn], [RE92; F, H, H, F , CF 3 ], [RE 93; F, H, H, F, CF 3 CH 2 ], [RE 94; F, H, H, F, CF 3 CF 2 ], [RE 95; F, H, H, F, CF 2 H], [RE 96; F, H, H, F, CF 2 HCH 2 ], [RE 97; H, F, H, F, Me], [RE 98; H, F, H, F, Et, [RE99; H, F, H, F, Pr], [RE 100; H, F, H, F, i-Pr], [RE 101; H, F, H, F, c-Pr], [RE 102; H, F, H, F, Bu], [RE 103; H, F, H, F, i-Bu], [RE 104; H, F, H, F, t- Bu], [RE 105; H, F, H, F, c-PrCH 2 ], [RE 106; H, F, H, F, Ph], [RE 107; H, F, H, F, Bn], [RE 108 H, F, H, F, CF 3 ], [RE 109; H, F, H, F, CF 3 CH 2 ], [RE 110; H, F, H, F, CF 3 CF 2 ], [RE 111; H, F, H, F, CF 2 H], [RE 112; H, F, H, F, CF 2 HCH 2 ]

式(VII)

Figure 2019089711
〔式中、R21、R22、R23、R24及びR25は上記と同じ意味を表す。〕
で表される化合物において、R21、R22、R23、R24及びR25の組合わせが下記に示される置換基番号RF1〜RF112のいずれかに記載の組合わせである化合物(以下、置換基番号RF1〜RF112の化合物を本発明化合物RF1〜RF112と表し、本発明化合物RF1〜RF112をまとめて本発明化合物RFと表す)は、上記の製造法に記載の方法に準じて得ることができる。
なお、置換基番号RF1〜RF112とは、式(VII)で表される化合物における、R21、R22、R23、R24及びR25の組合わせを表すものであり、以下、[置換基番号;R21,R22,R23,R24,R25]と記す。
例えば、置換基番号RF4とは、R21、R22、R23、及びR24が水素原子であり、R25がイソプロピル基である組合せを表す。 Formula (VII)
Figure 2019089711
[Wherein, R 21 , R 22 , R 23 , R 24 and R 25 represent the same meaning as described above. ]
In the compound represented by the above, a compound in which the combination of R 21 , R 22 , R 23 , R 24 and R 25 is a combination as described in any of the substituent numbers RF1 to RF112 shown below (hereinafter referred to as substitution The compounds of group numbers RF1 to RF112 are referred to as compounds of the present invention RF1 to RF112, and the compounds of the present invention RF1 to RF112 are collectively referred to as the compound of the present invention RF) can be obtained according to the method described in the above-mentioned production method .
In addition, the substituent numbers RF1 to RF112 represent a combination of R 21 , R 22 , R 23 , R 24 and R 25 in the compound represented by the formula (VII), and hereinafter, [Substituent Number: R 21 , R 22 , R 23 , R 24 , R 25 ].
For example, the substituent number RF4 represents a combination in which R 21 , R 22 , R 23 and R 24 are a hydrogen atom and R 25 is an isopropyl group.

例えば、本発明化合物RF4とは、式(VII)で表される化合物において置換基番号がRF4である化合物を意味し、式(VII)で表される化合物において、R21、R22、R23、及びR24が水素原子であり、R25がイソプロピル基である下記の化合物を表す。

Figure 2019089711
For example, the compound of the present invention RF4 means a compound represented by the formula (VII) in which the substituent number is RF4, and in the compound represented by the formula (VII), R 21 , R 22 and R 23 And R 24 is a hydrogen atom, and R 25 is an isopropyl group.
Figure 2019089711

[置換基番号;R21,R22,R23,R24,R25]:[RF1;H,H,H,H,Me],[RF2;H,H,H,H,Et],[RF3;H,H,H,H,Pr],[RF4;H,H,H,H,i-Pr],[RF5;H,H,H,H,c-Pr],[RF6;H,H,H,H,Bu],[RF7;H,H,H,H,i-Bu],[RF8;H,H,H,H,t-Bu],[RF9;H,H,H,H,c-PrCH2],[RF10;H,H,H,H,Ph],[RF11;H,H,H,H,Bn],[RF12;H,H,H,H,CF3],[RF13;H,H,H,H,CF3CH2],[RF14;H,H,H,H,CF3CF2],[RF15;H,H,H,H,CF2H],[RF16;H,H,H,H,CF2HCH2],[RF17;F,H,H,H,Me],[RF18;F,H,H,H,Et],[RF19;F,H,H,H,Pr],[RF20;F,H,H,H,i-Pr],[RF21;F,H,H,H,c-Pr],[RF22;F,H,H,H,Bu],[RF23;F,H,H,H,i-Bu],[RF24;F,H,H,H,t-Bu],[RF25;F,H,H,H,c-PrCH2],[RF26;F,H,H,H,Ph],[RF27;F,H,H,H,Bn],[RF28;F,H,H,H,CF3],[RF29;F,H,H,H,CF3CH2],[RF30;F,H,H,H,CF3CF2],[RF31;F,H,H,H,CF2H],[RF32;F,H,H,H,CF2HCH2],[RF33;H,F,H,H,Me],[RF34;H,F,H,H,Et],[RF35;H,F,H,H,Pr],[RF36;H,F,H,H,i-Pr],[RF37;H,F,H,H,c-Pr],[RF38;H,F,H,H,Bu],[RF39;H,F,H,H,i-Bu],[RF40;H,F,H,H,t-Bu],[RF41;H,F,H,H,c-PrCH2],[RF42;H,F,H,H,Ph],[RF43;H,F,H,H,Bn],[RF44;H,F,H,H,CF3],[RF45;H,F,H,H,CF3CH2],[RF46;H,F,H,H,CF3CF2],[RF47;H,F,H,H,CF2H],[RF48;H,F,H,H,CF2HCH2],[RF49;F,F,H,H,Me],[RF50;F,F,H,H,Et],[RF51;F,F,H,H,Pr],[RF52;F,F,H,H,i-Pr],[RF53;F,F,H,H,c-Pr],[RF54;F,F,H,H,Bu],[RF55;F,F,H,H,i-Bu],[RF56;F,F,H,H,t-Bu],[RF57;F,F,H,H,c-PrCH2],[RF58;F,F,H,H,Ph],[RF59;F,F,H,H,Bn],[RF60;F,F,H,H,CF3],[RF61;F,F,H,H,CF3CH2],[RF62;F,F,H,H,CF3CF2],[RF63;F,F,H,H,CF2H],[RF64;F,F,H,H,CF2HCH2],[RF65;F,H,F,H,Me],[RF66;F,H,F,H,Et],[RF67;F,H,F,H,Pr],[RF68;F,H,F,H,i-Pr],[RF69;F,H,F,H,c-Pr],[RF70;F,H,F,H,Bu],[RF71;F,H,F,H,i-Bu],[RF72;F,H,F,H,t-Bu],[RF73;F,H,F,H,c-PrCH2],[RF74;F,H,F,H,Ph],[RF75;F,H,F,H,Bn],[RF76;F,H,F,H,CF3],[RF77;F,H,F,H,CF3CH2],[RF78;F,H,F,H,CF3CF2],[RF79;F,H,F,H,CF2H],[RF80;F,H,F,H,CF2HCH2],[RF81;F,H,H,F,Me],[RF82;F,H,H,F,Et],[RF83;F,H,H,F,Pr],[RF84;F,H,H,F,i-Pr],[RF85;F,H,H,F,c-Pr],[RF86;F,H,H,F,Bu],[RF87;F,H,H,F,i-Bu],[RF88;F,H,H,F,t-Bu],[RF89;F,H,H,F,c-PrCH2],[RF90;F,H,H,F,Ph],[RF91;F,H,H,F,Bn],[RF92;F,H,H,F,CF3],[RF93;F,H,H,F,CF3CH2],[RF94;F,H,H,F,CF3CF2],[RF95;F,H,H,F,CF2H],[RF96;F,H,H,F,CF2HCH2],[RF97;H,F,H,F,Me],[RF98;H,F,H,F,Et],[RF99;H,F,H,F,Pr],[RF100;H,F,H,F,i-Pr],[RF101;H,F,H,F,c-Pr],[RF102;H,F,H,F,Bu],[RF103;H,F,H,F,i-Bu],[RF104;H,F,H,F,t-Bu],[RF105;H,F,H,F,c-PrCH2],[RF106;H,F,H,F,Ph],[RF107;H,F,H,F,Bn],[RF108;H,F,H,F,CF3],[RF109;H,F,H,F,CF3CH2],[RF110;H,F,H,F,CF3CF2],[RF111;H,F,H,F,CF2H],[RF112;H,F,H,F,CF2HCH2] [Substituent number; R 21 , R 22 , R 23 , R 24 , R 25 ]: [RF 1; H, H, H, H, Me], [RF 2; H, H, H, H, Et], [[ RF3, H, H, H, H, Pr, [RF4; H, H, H, H, i-Pr], [RF5; H, H, H, H, c-Pr], [RF6; H, H, H, H, Bu], [RF7; H, H, H, H, i, Bu], [RF 8; H, H, H, H, t, Bu], [RF 9; H, H, H, H H, c-PrCH 2], [RF10; H, H, H, H, Ph], [RF11; H, H, H, H, Bn], [RF12; H, H, H, H, CF 3] , [RF 13; H, H, H, H, CF 3 CH 2 ], [RF 14; H, H, H, H, CF 3 CF 2 ], [RF 15; H, H, H, H, CF 2 H] , [RF16; H, H, H, H, CF 2 HCH 2 ], [RF 17; F, H, H, H, Me], [RF 18; F, H, H, H, Et], [RF 19; F , H, H, H, Pr], [RF 20; F, H, H, H, i-Pr], [RF 21; F, H, H, H, c, Pr], [RF 22; F, H, H , H, Bu], [RF23; F, H, H, H, i-Bu], [RF 24; F, H, H, H, t-Bu], [RF 25; F, H, H, H, c -PrCH 2], [RF26; F , H, H, H, Ph], [RF27; F, H, H, H, Bn], [RF28; F, H, H, H, CF 3], [RF29 ; F, H, H, H , CF 3 CH 2], [RF30; F, H, H, H, CF 3 CF 2], [RF31; F, H, H, H, CF 2 H], [RF32 F, H, H, H, H, CF 2 HCH 2 ], [RF 33; H, F, H, H, Me], [RF 34; H, F, H, H, Et], [RF 35; H, F, H, H, Pr], [RF 36; H, F, H, H, i-Pr], [RF 37; H, F, H, H, c-Pr], [RF 38; H, F, H, H, H Bu], [RF 39; H, F, H, H, i-Bu], [RF 40; H, F, H, H, t-Bu], [RF 41; H, F, H, H, c-PrCH 2 ], [RF 42; H, F, H, H, Ph], [RF 43; H, F, H, H, Bn], [RF 44; H, F, H, H, CF 3 ], [RF 45; H, F, H, H, CF 3 CH 2 ], [RF 46; H, F, H, H, CF 3 CF 2 ], [RF 47 H, F, H, H, CF 2 H], [RF 48; H, F, H, H, CF 2 HCH 2 ], [RF 49; F, F, H, H, Me], [RF 50; F, F, H, H, Et], [RF 51; F, F, H, H, Pr], [RF 52; F, F, H, H, i-Pr], [RF 53; F, F, H, H, c-Pr], [RF 54; F, F, H, H, Bu], [RF 55; F, F, H, H, i-Bu], [RF 56; F, F, H, H, t-Bu] , [RF57; F, F, H, H, c-PrCH 2], [RF58; F, F, H, H, Ph], [RF59; F, F, H, H, Bn], [RF60; F , F, H, H, CF 3 ], [RF 61; F, F, H, H, CF 3 CH 2 ], [RF 62; F, F, H, H, CF 3 CF 2 ], [RF 63; F, F, H, H, CF 2 H], [RF 64; F, F, H, H, CF 2 HCH 2 ], [RF 65; F, H, F, H, Me], [RF 66; F, H, F , H, Et], [RF67; F, H, F, H, Pr], [RF 68; F, H, F, H, i-Pr], [RF 69; F, H, F, H, c-Pr ], [RF 70; F, H, F, H, Bu], [RF 71; F, H, F, H, i-Bu], [RF 72; F, H, F, H, t-Bu], [RF 73] F, H, F, H, c-PrCH 2 ], [RF 74; F, H, F, H, Ph], [RF 75; F, H, F, H, Bn], [RF 76; F, H, F, H, CF 3 ], [RF 77; F, H, F, H, CF 3 CH 2 ], [RF 78; F, H, F, H, CF 3 CF 2 ], [RF 79; F, H, F , H, CF 2 H], [RF80; F, H, F, H, CF 2 HCH 2], [RF81; F, H, H, F, Me], [RF82; F, H, H, F, Et], [RF 83; F, H, H, F, Pr], [RF 84; F, H, H, F, i-Pr], [RF 85; F, H, H, F, c-Pr], [[ RF86; F, H, H, F, Bu], [RF 87; F, H, H, F, i-Bu], [RF 88; F, H, H, F, t-Bu], [RF 89; F, H, H, F, c- PrCH 2], [RF90; F, H, H, F, Ph], [RF91; F, H, H, F, Bn], [RF92; F, H, H, F , CF 3 ], [RF 93; F, H, H, F, CF 3 CH 2 ], [RF 94; F, H, H, F, CF 3 CF 2 ], [RF 95; F, H, H, F, CF 2 H], [RF 96; F, H, H, F, CF 2 HCH 2 ], [RF 97; H, F, H, F, Me], [RF 98; H, F, H, F, Et], [RF 99; H, F, H, F, Pr], [RF 100; H, F, H, F, i-Pr], [RF 101; H, F, H, F, c-Pr], [RF 102; H, F, H, F, Bu], [RF 103; H, F, H, F, i-Bu], [RF 104; H, F, H, F, t- Bu], [RF 105; H, F, H, F, c-PrCH 2 ], [RF 106; H, F, H, F, Ph], [RF 107; H, F, H, F, Bn], [RF 108 H, F, H, F, CF 3 ], [RF 109; H, F, H, F, CF 3 CH 2 ], [RF 110; H, F, H, F, CF 3 CF 2 ], [RF 111; H, F, H, F, CF 2 H], [RF112; H, F, H, F, CF 2 HCH 2]

式(VIII)

Figure 2019089711
〔式中、R25は上記と同じ意味を表し、Q21は酸素原子又はNR7を表す。〕
で表される化合物において、Q21及びR25の組合わせが下記に示される置換基番号RG1〜RG30のいずれかに記載の組合わせである化合物(以下、置換基番号RG1〜RG30の化合物を本発明化合物RG1〜RG30と表し、本発明化合物RG1〜RG30をまとめて本発明化合物RGと表す)は、上記の製造法に記載の方法に準じて得ることができる。
なお、置換基番号RG1〜RG30とは、式(VIII)で表される化合物における、Q21及びR25の組合せを表すものであり、以下、[置換基番号;Q21,R25]と記す。
例えば、置換基番号RG4とは、Q21が酸素原子であり、R25がイソプロピル基である組合せを表す。 Formula (VIII)
Figure 2019089711
[Wherein, R 25 represents the same meaning as described above, and Q 21 represents an oxygen atom or NR 7 . ]
Wherein the combination of Q 21 and R 25 is a combination as set forth in any one of Substituent Nos. RG 1 to RG 30 (hereinafter referred to as “compound of Substituent No. RG 1 to RG 30”) Inventive compounds RG1 to RG30, and the compounds of the present invention RG1 to RG30 are collectively referred to as the compound of the present invention RG) can be obtained according to the method described in the above-mentioned production method.
Substituent numbers RG1 to RG30 each represent a combination of Q 21 and R 25 in the compound represented by formula (VIII), and hereinafter referred to as [substituent number: Q 21 , R 25 ]. .
For example, substituent number RG4 represents a combination wherein Q 21 is an oxygen atom and R 25 is an isopropyl group.

例えば、本発明化合物RG4とは、式(VIII)で表される化合物において置換基番号がRG4である化合物を意味し、式(VIII)で表される化合物において、Q21が酸素原子であり、R25がイソプロピル基である下記の化合物を表す。

Figure 2019089711
For example, the compound RG4 of the present invention means a compound represented by the formula (VIII) in which the substituent number is RG4, and in the compound represented by the formula (VIII), Q 21 is an oxygen atom, Represents the following compound wherein R 25 is an isopropyl group.
Figure 2019089711

[置換基番号;Q21,R25]:[RG1;O,Me],[RG2;O,Et],[RG3;O,Pr],[RG4;O,i-Pr],[RG5;O,c-Pr],[RG6;O,Bu],[RG7;O,t-Bu],[RG8;O,c-PrCH2],[RG9;O,Ph],[RG10;O,Bn],[RG11;O,CF3],[RG12;O,CF3CH2],[RG13;O,CF3CF2],[RG14;O,CF2H],[RG15;O,CF2HCH2],[RG16;NH,Me],[RG17;NH,Et],[RG18;NH,Pr],[RG19;NH,i-Pr],[RG20;NH,c-Pr],[RG21;NH,Bu],[RG22;NH,t-Bu],[RG23;NH,c-PrCH2],[RG24;NH,Ph],[RG25;NH,Bn],[RG26;NH,CF3],[RG27;NH,CF3CH2],[RG28;NH,CF3CF2],[RG29;NH,CF2H],[RG30;NH,CF2HCH2] [Substituent No. Q 21 , R 25 ]: [RG1; O, Me], [RG2; O, Et], [RG3; O, Pr], [RG4; O, i-Pr], [RG5; , c-Pr], [RG6 ; O, Bu], [RG7; O, t-Bu], [RG8; O, c-PrCH 2], [RG9; O, Ph], [RG10; O, Bn] , [RG11; O, CF 3 ], [RG12; O, CF 3 CH 2], [RG13; O, CF 3 CF 2], [RG14; O, CF 2 H], [RG15; O, CF 2 HCH 2 ], [RG16; NH, Me], [RG17; NH, Et], [RG18; NH, Pr], [RG19; NH, i-Pr], [RG20; NH, c-Pr], [RG21; NH, Bu], [RG22; NH, t-Bu], [RG23; NH, c-PrCH 2], [RG24; NH, Ph], [RG25; NH, Bn], [RG26; NH, CF 3] , [RG27; NH, CF 3 CH 2], [RG28; NH, CF 3 CF 2], [RG29; NH, CF 2 H], [RG30; NH, CF 2 HCH 2]

式(IX)

Figure 2019089711
〔式中、R25は上記と同じ意味を表し、R26はNO2、C(O)R7、C(O)OR7又はS(O)27を表す。〕で表される化合物において、R25及びR26の組合わせが下記に示される置換基番号RH1〜RH54のいずれかに記載の組合わせである化合物(以下、置換基番号RH1〜RH54の化合物を本発明化合物RH1〜RH54と表し、本発明化合物RH1〜RH54をまとめて本発明化合物RHと表す)は、上記の製造法に記載の方法に準じて得ることができる。
なお、置換基番号RH1〜RH54とは、式(IX)で表される化合物における、R25及びR26の組合せを表すものであり、以下、[置換基番号;R25,R26]と記す。
例えば、置換基番号RH4とは、R25がシクロプロピル基であり、R26がC(O)Meである組合せを表す。 Formula (IX)
Figure 2019089711
[Wherein, R 25 represents the same meaning as described above, and R 26 represents NO 2 , C (O) R 7 , C (O) OR 7 or S (O) 2 R 7 . In which R 25 and R 26 are a combination of any of Substituent Nos. RH 1 to RH 54 shown below (hereinafter referred to as compounds of Substituent Nos. RH 1 to RH 54) The compounds of the present invention RH1 to RH54, and the compounds of the present invention RH1 to RH54 are collectively referred to as the compound of the present invention RH) can be obtained according to the method described in the above production method.
The substituent numbers RH1 to RH54 represent the combination of R 25 and R 26 in the compound represented by the formula (IX), and hereinafter referred to as [substituent number; R 25 , R 26 ] .
For example, the substituent number RH4 represents a combination wherein R 25 is a cyclopropyl group and R 26 is C (O) Me.

例えば、本発明化合物RH4とは、式(IX)で表される化合物において置換基番号がRH4である化合物を意味し、式(IX)で表される化合物において、R25がシクロプロピル基であり、R26がC(O)Meである下記の化合物を表す。

Figure 2019089711
For example, the compound RH4 of the present invention means a compound represented by the formula (IX) wherein the substituent number is RH4, and in the compound represented by the formula (IX), R 25 is a cyclopropyl group , R 26 is C (O) Me.
Figure 2019089711

[置換基番号;R25,R26]:[RH1;Me,C(O)Me],[RH2;Et,C(O)Me],[RH3;i-Pr,C(O)Me],[RH4;c-Pr,C(O)Me],[RH5;CF2H,C(O)Me],[RH6;CF3,C(O)Me],[RH7;Me,C(O)Et],[RH8;Et,C(O)Et],[RH9;i-Pr,C(O)Et],[RH10;c-Pr,C(O)Et],[RH11;CF2H,C(O)Et],[RH12;CF3,C(O)Et],[RH13;Me,C(O)CF3],[RH14;Et,C(O)CF3],[RH15;i-Pr,C(O)CF3],[RH16;c-Pr,C(O)CF3],[RH17;CF2H,C(O)CF3],[RH18;CF3,C(O)CF3],[RH19;Me,C(O)OMe],[RH20;Et,C(O)OMe],[RH21;i-Pr,C(O)OMe],[RH22;c-Pr,C(O)OMe],[RH23;CF2H,C(O)OMe],[RH24;CF3,C(O)OMe],[RH25;Me,C(O)OEt],[RH26;Et,C(O)OEt],[RH27;i-Pr,C(O)OEt],[RH28;c-Pr,C(O)OEt],[RH29;CF2H,C(O)OEt],[RH30;CF3,C(O)OEt],[RH31;Me,S(O)2Me],[RH32;Et,S(O)2Me],[RH33;i-Pr,S(O)2Me],[RH34;c-Pr,S(O)2Me],[RH35;CF2H,S(O)2Me],[RH36;CF3,S(O)2Me],[RH37;Me,S(O)2Et],[RH38;Et,S(O)2Et],[RH39;i-Pr,S(O)2Et],[RH40;c-Pr,S(O)2Et],[RH41;CF2H,S(O)2Et],[RH42;CF3,S(O)2Et],[RH43;Me,S(O)2CF3],[RH44;Et,S(O)2CF3],[RH45;i-Pr,S(O)2CF3],[RH46;c-Pr,S(O)2CF3],[RH47;CF2H,S(O)2CF3],[RH48;CF3,S(O)2CF3],[RH49;Me,C(O)CF2H],[RH50;Et,C(O)CF2H],[RH51;i-Pr,C(O)CF2H],[RH52;c-Pr,C(O)CF2H],[RH53;CF2H,C(O)CF2H],[RH54;CF3,C(O)CF2H] [Substituent number; R 25 , R 26 ]: [RH 1; Me, C (O) Me], [RH 2; Et, C (O) Me], [RH 3; i-Pr, C (O) Me], [RH4; c-Pr, C (O) Me], [RH5; CF 2 H, C (O) Me], [RH6; CF 3, C (O) Me], [RH7; Me, C (O) Et], [RH 8; Et, C (O) Et], [RH 9; i-Pr, C (O) Et], [RH 10; c-Pr, C (O) Et], [RH 11; CF 2 H, C (O) Et], [ RH12; CF 3, C (O) Et], [RH13; Me, C (O) CF 3], [RH14; Et, C (O) CF 3], [RH15; i -Pr, C (O) CF 3 ], [RH16; c-Pr, C (O) CF 3], [RH17; CF 2 H, C (O) CF 3], [RH18; CF 3, C (O ) CF 3 ], [RH 19; Me, C (O) OMe], [RH 20; Et, C (O) OMe], [RH 21; i-Pr, C (O) OMe], [RH 22; c-Pr, C (O) OMe], [ RH23; CF 2 H, C (O) OMe], [RH24; CF 3, C (O) OMe], [RH25; Me, C (O) OEt], [RH26; Et , C (O) OEt], [RH27; i-Pr, C (O) OEt], [RH28; c-Pr, C (O) OEt], [RH29; CF 2 H, C (O) OEt], [RH30; CF 3, C ( O) OEt], [RH31; Me, S (O) 2 Me], [RH32; Et, S (O) 2 Me], [RH33; i-Pr, S (O) 2 Me !, [RH 34; c-Pr, S (O) 2 Me], [RH 35; CF 2 H, S (O) 2 Me], [RH 36; CF 3 , S (O) 2 Me], [RH 37 Me, S (O) 2 Et], [RH 38; Et, S (O) 2 Et], [RH 39; i-Pr, S (O) 2 Et], [RH 40; c-Pr, S (O) 2 Et], [RH 41; CF 2 H, S (O) 2 Et], [RH 42; CF 3 , S (O) 2 Et], [RH 43; Me, S (O) 2 CF 3 ], [RH 44; Et, S (O) 2 CF 3 ], [RH 45; i-Pr, S (O) 2 CF 3 ], [RH 46; c-Pr, S (O) 2 CF 3 ], [RH 47; CF 2 H, S (O) 2 CF 3 ], [RH 48; CF 3 , S (O) 2 CF 3 ], [RH 49; Me, C (O) CF 2 H], [RH 50; Et, C (O) CF 2 H], [RH 51; Pr, C (O) CF 2 H], [RH52; c-Pr, C (O) CF 2 H], [RH53; CF 2 H, C (O) CF 2 H], [RH54; CF 3, C (O) CF 2 H]

式(X)

Figure 2019089711
〔式中、R25及びQ21は上記と同じ意味を表す。〕
で表される化合物において、Q21及びR25の組合わせが下記に示される置換基番号RI1〜RI30のいずれかに記載の組合わせである化合物(以下、置換基番号RI1〜RI30の化合物を本発明化合物RI1〜RI30と表し、本発明化合物RI1〜RI30をまとめて本発明化合物RIと表す)は、上記の製造法に記載の方法に準じて得ることができる。
なお、置換基番号RI1〜RI30とは、式(X)で表される化合物における、Q21及びR25の組合せを表すものであり、以下、[置換基番号;Q21,R25]と記す。
例えば、置換基番号RI4とは、Q21が酸素原子であり、R25がイソプロピル基である組合せを表す。 Formula (X)
Figure 2019089711
[Wherein, R 25 and Q 21 represent the same meaning as described above. ]
Wherein the combination of Q 21 and R 25 is a combination as set forth in any one of Substituent Nos. RI 1 to RI 30 (hereinafter referred to as “compound of Substituent Nos. RI 1 to RI 30” Invention compounds RI1 to RI30, and the compounds of the present invention RI1 to RI30 are collectively referred to as the compounds of the invention RI) can be obtained according to the method described in the above-mentioned production method.
Note that the substituent number RI1~RI30, in the compound of formula (X), and represents the combination of Q 21 and R 25, or less; referred to as Substituent number Q 21, R 25] .
For example, the substituent number RI4 represents a combination in which Q 21 is an oxygen atom and R 25 is an isopropyl group.

例えば、本発明化合物RI4とは、式(X)で表される化合物において置換基番号がRI4である化合物を意味し、式(X)で表される化合物において、Q21が酸素原子であり、R25がイソプロピル基である下記の化合物を表す。

Figure 2019089711
For example, the compound of the present invention RI4 means a compound represented by the formula (X) in which the substituent number is RI4, and in the compound represented by the formula (X), Q 21 is an oxygen atom, Represents the following compound wherein R 25 is an isopropyl group.
Figure 2019089711

[置換基番号;Q21,R25]:[RI1;O,Me],[RI2;O,Et],[RI3;O,Pr],[RI4;O,i-Pr],[RI5;O,c-Pr],[RI6;O,Bu],[RI7;O,t-Bu],[RI8;O,c-PrCH2],[RI9;O,Ph],[RI10;O,Bn],[RI11;O,CF3],[RI12;O,CF3CH2],[RI13;O,CF3CF2],[RI14;O,CF2H],[RI15;O,CF2HCH2],[RI16;NH,Me],[RI17;NH,Et],[RI18;NH,Pr],[RI19;NH,i-Pr],[RI20;NH,c-Pr],[RI21;NH,Bu],[RI22;NH,t-Bu],[RI23;NH,c-PrCH2],[RI24;NH,Ph],[RI25;NH,Bn],[RI26;NH,CF3],[RI27;NH,CF3CH2],[RI28;NH,CF3CF2],[RI29;NH,CF2H],[RI30;NH,CF2HCH2] [Substituent No. Q 21 , R 25 ]: [RI 1; O, Me], [RI 2; O, Et], [RI 3; O, Pr], [RI 4; O, i-Pr], [RI 5; , c-Pr], [RI 6; O, Bu], [RI 7; O, t-Bu], [RI 8; O, c-PrCH 2 ], [RI 9; O, Ph], [RI 10; O, Bn] , [RI 11; O, CF 3 ], [RI 12; O, CF 3 CH 2 ], [RI 13; O, CF 3 CF 2 ], [RI 14; O, CF 2 H], [RI 15; O, CF 2 HCH 2 ], [RI 16; NH, Me], [RI 17; NH, Et, [RI 18; NH, Pr], [RI 19; NH, i-Pr], [RI 20; NH, c-Pr], [RI 21; NH, Bu], [RI 22; NH, t-Bu], [RI 23; NH, c-PrCH 2 ], [RI 24; NH, Ph], [RI 25; NH, Bn], [RI 26; NH, CF 3 ] , [RI 27; NH, CF 3 CH 2 ], [RI 28; NH, CF 3 CF 2 ], [RI 29; NH, CF 2 H], [RI 30; NH, CF 2 HCH 2 ]

式(XI)

Figure 2019089711
〔式中、R25及びQ21は上記と同じ意味を表す。〕
で表される化合物において、Q21及びR25の組合わせが下記に示される置換基番号RJ1〜RJ30のいずれかに記載の組合わせである化合物(以下、置換基番号RJ1〜RJ30の化合物を本発明化合物RJ1〜RJ30と表し、本発明化合物RJ1〜RJ30をまとめて本発明化合物RJと表す)は、上記の製造法に記載の方法に準じて得ることができる。
なお、置換基番号RJ1〜RJ30とは、式(XI)で表される化合物における、Q21及びR25の組合せを表すものであり、以下、[置換基番号;Q21,R25]と記す。
例えば、置換基番号RJ4とは、Q21が酸素原子であり、R25がイソプロピル基である組合せを表す。 Formula (XI)
Figure 2019089711
[Wherein, R 25 and Q 21 represent the same meaning as described above. ]
Wherein the combination of Q 21 and R 25 is a combination as set forth in any of Substituent Nos. RJ 1 to RJ 30 (hereinafter referred to as the compound of Substituent No. RJ 1 to RJ 30) Inventive compounds RJ1 to RJ30, and the compounds of the present invention RJ1 to RJ30 are collectively referred to as the compound of the invention RJ) can be obtained according to the method described in the above-mentioned production method.
Substituent numbers RJ1 to RJ30 represent the combination of Q 21 and R 25 in the compound represented by formula (XI), and hereinafter referred to as [substituent number: Q 21 , R 25 ] .
For example, the substituent number RJ4 represents a combination in which Q 21 is an oxygen atom and R 25 is an isopropyl group.

例えば、本発明化合物RJ4とは、(XI)で表される化合物において置換基番号がRJ4である化合物を意味し、式(XI)で表される化合物において、Q21が酸素原子であり、R25がイソプロピル基である下記の化合物を表す。

Figure 2019089711
For example, the compound RJ4 of the present invention means a compound having a substituent number of RJ4 in the compound represented by (XI), and in the compound represented by the formula (XI), Q 21 is an oxygen atom, R 25 represents the following compound in which an isopropyl group is present.
Figure 2019089711

[置換基番号;Q21,R25]:[RJ1;O,Me],[RJ2;O,Et],[RJ3;O,Pr],[RJ4;O,i-Pr],[RJ5;O,c-Pr],[RJ6;O,Bu],[RJ7;O,t-Bu],[RJ8;O,c-PrCH2],[RJ9;O,Ph],[RJ10;O,Bn],[RJ11;O,CF3],[RJ12;O,CF3CH2],[RJ13;O,CF3CF2],[RJ14;O,CF2H],[RJ15;O,CF2HCH2],[RJ16;NH,Me],[RJ17;NH,Et],[RJ18;NH,Pr],[RJ19;NH,i-Pr],[RJ20;NH,c-Pr],[RJ21;NH,Bu],[RJ22;NH,t-Bu],[RJ23;NH,c-PrCH2],[RJ24;NH,Ph],[RJ25;NH,Bn],[RJ26;NH,CF3],[RJ27;NH,CF3CH2],[RJ28;NH,CF3CF2],[RJ29;NH,CF2H],[RJ30;NH,CF2HCH2] [Substituent number: Q 21 , R 25 ]: [RJ 1; O, Me], [RJ 2; O, Et], [RJ 3; O, Pr], [RJ 4; O, i-Pr], [RJ 5; , c-Pr], [RJ6; O, Bu], [RJ 7; O, t-Bu], [RJ 8; O, c-PrCH 2 ], [RJ 9; O, Ph], [RJ 10; O, Bn] , [RJ11; O, CF 3 ], [RJ12; O, CF 3 CH 2], [RJ13; O, CF 3 CF 2], [RJ14; O, CF 2 H], [RJ15; O, CF 2 HCH 2 ], [RJ 16; NH, Me], [RJ 17; NH, Et], [RJ 18; NH, Pr], [RJ 19; NH, i-Pr], [RJ 20; NH, c-Pr], [RJ 21; NH, Bu], [RJ 22; NH, t-Bu], [RJ 23; NH, c-PrCH 2 ], [RJ 24; NH, Ph], [RJ 25; NH, Bn], [RJ 26; NH, CF 3 ] , [RJ27; NH, CF 3 CH 2], [RJ28; NH, CF 3 CF 2], [RJ29; NH, CF 2 H], [RJ30; NH, CF 2 HCH 2]

式(XII)

Figure 2019089711
〔式中、R25は上記と同じ意味を表し、R31は水素原子、群Aより選ばれる1以上の置換基を有していてもよいC1−C6アルキル基、1以上のハロゲン原子を有していてもよいC3−C6アルキニル基、1以上のハロゲン原子を有していてもよいC1−C6アルコキシ基、群Dより選ばれる1以上の置換基を有していてもよいC3−C6シクロアルキル基もしくは群Dより選ばれる1以上の置換基を有していてもよいフェニル基を表すか、又は、R25とR31とは、互いに結合して5−7員ヘテロ環(該5−7員ヘテロ環は群Dより選ばれる1以上の置換基を有していてもよい)を形成していてもよい。〕
で表される化合物において、R31及びR25の組合わせが下記に示される置換基番号RK1〜RK407のいずれかに記載の組合わせである化合物(以下、置換基番号RK1〜RK407の化合物を本発明化合物RK1〜RK407と表し、本発明化合物RK1〜RK407をまとめて本発明化合物RKと表す)は、上記の製造法に記載の方法に準じて得ることができる。
なお、置換基番号RK1〜RK407とは、式(XII)で表される化合物における、R31及びR25の組合せを表すものであり、以下、[置換基番号;R31,R25]と記す。ただし、置換基番号RK166及びRK167においては、R31とR25とが、互いに結合してヘテロ環を形成することを表す。
例えば、置換基番号RK4とは、R31が水素原子であり、R25がイソプロピル基である組合せを表す。 Formula (XII)
Figure 2019089711
[Wherein, R 25 represents the same meaning as above, and R 31 has a hydrogen atom, a C1-C6 alkyl group optionally having one or more substituents selected from group A, and one or more halogen atoms] C3-C6 alkynyl group which may be substituted, C1-C6 alkoxy group which may have one or more halogen atoms, C3-C6 cyclo group which may have one or more substituents selected from group D R 25 represents an alkyl group or a phenyl group which may have one or more substituents selected from group D, or R 25 and R 31 are bonded to each other to form a 5- to 7-membered heterocyclic ring The 7-membered heterocycle may form one or more substituents selected from Group D). ]
Wherein the combination of R 31 and R 25 is a combination as set forth in any of Substituent Nos. RK 1 to R K 407 as shown below (hereinafter referred to as “compound of Substituent Nos. RK 1 to RK 407” Inventive compounds RK1 to RK407, and the compounds of the present invention RK1 to RK407 are collectively referred to as the compounds of the present invention RK) can be obtained according to the method described in the above-mentioned production method.
Note that the substituent number RK1~RK407, in the compound of formula (XII), and represents the combination of R 31 and R 25, or less; referred to as Substituent Number R 31, R 25] . However, in the substituent numbers RK166 and RK167, it represents that R 31 and R 25 bond with each other to form a heterocycle.
For example, the substituent number RK4 represents a combination in which R 31 is a hydrogen atom and R 25 is an isopropyl group.

25とR31とが互いに結合して形成される5−7員ヘテロ環とは、下記(ZF11〜ZF13)に示すいずれかの構造を表す(●は結合位置を表す)。

Figure 2019089711
The 5-7 membered heterocyclic ring formed by bonding R 25 and R 31 to each other represents any of the structures shown in the following (ZF 11 to ZF 13) (● represents a bonding position).
Figure 2019089711

例えば、本発明化合物RK4とは、式(XII)で表される化合物において置換基番号がRK4である化合物を意味し、式(XII)で表される化合物において、R31が水素原子であり、R25がイソプロピル基である下記の化合物を表す。

Figure 2019089711
For example, the compound RK4 of the present invention means a compound represented by the formula (XII) in which the substituent number is RK4, and in the compound represented by the formula (XII), R 31 is a hydrogen atom, Represents the following compound wherein R 25 is an isopropyl group.
Figure 2019089711

[置換基番号;R31,R25]:[RK1;H,Me],[RK2;H,Et],[RK3;H,Pr],[RK4;H,i-Pr],[RK5;H,c-Pr],[RK6;H,Bu],[RK7;H,t-Bu],[RK8;H,c-PrCH2],[RK9;H,Ph],[RK10;H,Bn],[RK11;H,CF3],[RK12;H,CF3CH2],[RK13;H,CF3CF2],[RK14;H,CF2H],[RK15;H,CF2HCH2],[RK16;Me,Me],[RK17;Me,Et],[RK18;Me,Pr],[RK19;Me,i-Pr],[RK20;Me,c-Pr],[RK21Me,Bu],[RK22;Me,t-Bu],[RK23;Me,c-PrCH2],[RK24;Me,Ph],[RK25;Me,Bn],[RK26;Me,CF3],[RK27;Me,CF3CH2],[RK28;Me,CF3CF2],[RK29;Me,CF2H],[RK30;Me,CF2HCH2],[RK31;Et,Me],[RK32;Et,Et],[RK33;Et,Pr],[RK34;Et,i-Pr],[RK35;Et,c-Pr],[RK36;Et,Bu],[RK37;Et,t-Bu],[RK38;Et,c-PrCH2],[RK39;Et,Ph],[RK40;Et,Bn],[RK41;Et,CF3],[RK42;Et,CF3CH2],[RK43;Et,CF3CF2],[RK44;Et,CF2H],[RK45;Et,CF2HCH2],[RK46;Pr,Me],[RK47;Pr,Et],[RK48;Pr,Pr],[RK49;Pr,i-Pr],[RK50;Pr,c-Pr],[RK51;Pr,Bu],[RK52;Pr,t-Bu],[RK53;Pr,c-PrCH2],[RK54;Pr,Ph],[RK55;Pr,Bn],[RK56;Pr,CF3],[RK57;Pr,CF3CH2],[RK58;Pr,CF3CF2],[RK59;Pr,CF2H],[RK60;Pr,CF2HCH2],[RK61;i-Pr,Me],[RK62;i-Pr,Et],[RK63;i-Pr,Pr],[RK64;i-Pr,i-Pr],[RK65;i-Pr,c-Pr],[RK66;i-Pr,Bu],[RK67;i-Pr,t-Bu],[RK68;i-Pr,c-PrCH2],[RK69;i-Pr,Ph],[RK70;i-Pr,Bn],[RK71;i-Pr,CF3],[RK72;i-Pr,CF3CH2],[RK73;i-Pr,CF3CF2],[RK74;i-Pr,CF2H],[RK75;i-Pr,CF2HCH2],[RK76;c-Pr,Me],[RK77;c-Pr,Et],[RK78;c-Pr,Pr],[RK79;c-Pr,i-Pr],[RK80;c-Pr,c-Pr],[RK81;c-Pr,Bu],[RK82;c-Pr,t-Bu],[RK83;c-Pr,c-PrCH2],[RK84;c-Pr,Ph],[RK85;c-Pr,Bn],[RK86;c-Pr,CF3],[RK87;c-Pr,CF3CH2],[RK88;c-Pr,CF3CF2],[RK89;c-Pr,CF2H],[RK90;c-Pr,CF2HCH2],[RK91;c-PrCH2,Me],[RK92;c-PrCH2,Et],[RK93;c-PrCH2,Pr],[RK94;c-PrCH2,i-Pr],[RK95;c-PrCH2,c-Pr],[RK96;c-PrCH2,Bu],[RK97;c-PrCH2,t-Bu],[RK98;c-PrCH2,c-PrCH2],[RK99;c-PrCH2,Ph],[RK100;c-PrCH2,Bn],[RK101;c-PrCH2,CF3],[RK102;c-PrCH2,CF3CH2],[RK103;c-PrCH2,CF3CF2],[RK104;c-PrCH2,CF2H],[RK105;c-PrCH2,CF2HCH2],[RK106;CF3CH2,Me],[RK107;CF3CH2,Et],[RK108;CF3CH2,Pr],[RK109;CF3CH2,i-Pr],[RK110;CF3CH2,c-Pr],[RK111;CF3CH2,Bu],[RK112;CF3CH2,t-Bu],[RK113;CF3CH2,c-PrCH2],[RK114;CF3CH2,Ph],[RK115;CF3CH2,Bn],[RK116;CF3CH2,CF3],[RK117;CF3CH2,CF3CH2],[RK118;CF3CH2,CF3CF2],[RK119;CF3CH2,CF2H],[RK120;CF3CH2,CF2HCH2],[RK121;CF2HCH2,Me],[RK122;CF2HCH2,Et],[RK123;CF2HCH2,Pr],[RK124;CF2HCH2,i-Pr],[RK125;CF2HCH2,c-Pr],[RK126;CF2HCH2,Bu],[RK127;CF2HCH2,t-Bu],[RK128;CF2HCH2,c-PrCH2],[RK129;CF2HCH2,Ph],[RK130;CF2HCH2,Bn],[RK131;CF2HCH2,CF3],[RK132;CF2HCH2,CF3CH2],[RK133;CF2HCH2,CF3CF2],[RK134;CF2HCH2,CF2H],[RK135;CF2HCH2,CF2HCH2],[RK136;MeOCH2,Me],[RK137;MeOCH2,Et],[RK138;MeOCH2,Pr],[RK139;MeOCH2,i-Pr],[RK140;MeOCH2,c-Pr],[RK141;MeOCH2,Bu],[RK142;MeOCH2,t-Bu],[RK143;MeOCH2,c-PrCH2],[RK144;MeOCH2,Ph],[RK145;MeOCH2,Bn],[RK146;MeOCH2,CF3],[RK147;MeOCH2,CF3CH2],[RK148;MeOCH2,CF3CF2],[RK149;MeOCH2,CF2H],[RK150;MeOCH2,CF2HCH2],[RK151;EtOCH2,Me],[RK152;EtOCH2,Et],[RK153;EtOCH2,Pr],[RK154;EtOCH2,i-Pr],[RK155;EtOCH2,c-Pr],[RK156;EtOCH2,Bu],[RK157;EtOCH2,t-Bu],[RK158;EtOCH2,c-PrCH2],[RK159;EtOCH2,Ph],[RK160;EtOCH2,Bn],[RK161;EtOCH2,CF3],[RK162;EtOCH2,CF3CH2],[RK163;EtOCH2,CF3CF2],[RK164;EtOCH2,CF2H],[RK165;EtOCH2,CF2HCH2],[RK166;CH2CH2CH2],[RK167;CH2CH2CH2CH2],[RK168;t-Bu,Me],[RK169;t-Bu,Et],[RK170;t-Bu,Pr],[RK171;t-Bu,i-Pr],[RK172;t-Bu,c-Pr],[RK173;t-Bu,t-Bu],[RK174;t-Bu,Bu],[RK175;t-Bu,t-Bu],[RK176;t-Bu,c-PrCH2],[RK177;t-Bu,Ph],[RK178;t-Bu,Bn],[RK179;t-Bu,CF3],[RK180;t-Bu,CF3CH2],[RK181;t-Bu,CF3CF2],[RK182;t-Bu,CF2H],[RK183;t-Bu,CF2HCH2],[RK184;i-Bu,Me],[RK185;i-Bu,Et],[RK186;i-Bu,Pr],[RK187;i-Bu,i-Pr],[RK188;i-Bu,c-Pr],[RK189;i-Bu,t-Bu],[RK190;i-Bu,Bu],[RK191;i-Bu,t-Bu],[RK192;i-Bu,c-PrCH2],[RK193;i-Bu,Ph],[RK194;i-Bu,Bn],[RK195;i-Bu,CF3],[RK196;i-Bu,CF3CH2],[RK197;i-Bu,CF3CF2],[RK198;i-Bu,CF2H],[RK199;i-Bu,CF2HCH2],[RK200;HCCCH2,Me],[RK201;HCCCH2,Et],[RK202;HCCCH2,Pr],[RK203;HCCCH2,i-Pr],[RK204;HCCCH2,c-Pr],[RK205;HCCCH2,t-Bu],[RK206;HCCCH2,Bu],[RK207;HCCCH2,t-Bu],[RK208;HCCCH2,c-PrCH2],[RK209;HCCCH2,Ph],[RK210;HCCCH2,Bn],[RK211;HCCCH2,CF3],[RK212;HCCCH2,CF3CH2],[RK213;HCCCH2,CF3CF2],[RK214;HCCCH2,CF2H],[RK215;HCCCH2,CF2HCH2],[RK216;MeCCCH2,Me],[RK217;MeCCCH2,Et],[RK218;MeCCCH2,Pr],[RK219;MeCCCH2,i-Pr],[RK220;MeCCCH2,c-Pr],[RK221;MeCCCH2,t-Bu],[RK222;MeCCCH2,Bu],[RK223;MeCCCH2,t-Bu],[RK224;MeCCCH2,c-PrCH2],[RK225;MeCCCH2,Ph],[RK226;MeCCCH2,Bn],[RK227;MeCCCH2,CF3],[RK228;MeCCCH2,CF3CH2],[RK229;MeCCCH2,CF3CF2],[RK230;MeCCCH2,CF2H],[RK231;MeCCCH2,CF2HCH2],[RK232;MeSCH2,Me],[RK233;MeSCH2,Et],[RK234;MeSCH2,Pr],[RK235;MeSCH2,i-Pr],[RK236;MeSCH2,c-Pr],[RK237;MeSCH2,t-Bu],[RK238;MeSCH2,Bu],[RK239;MeSCH2,t-Bu],[RK240;MeSCH2,c-PrCH2],[RK241;MeSCH2,Ph],[RK242;MeSCH2,Bn],[RK243;MeSCH2,CF3],[RK244;MeSCH2,CF3CH2],[RK245;MeSCH2,CF3CF2],[RK246;MeSCH2,CF2H],[RK247;MeSCH2,CF2HCH2],[RK248;EtSCH2,Me],[RK249;EtSCH2,Et],[RK250;EtSCH2,Pr], [Substituent number; R 31 , R 25 ]: [RK1; H, Me], [RK2; H, Et], [RK3; H, Pr], [RK4; H, i-Pr], [RK5; H , c-Pr], [RK6 ; H, Bu], [RK7; H, t-Bu], [RK8; H, c-PrCH 2], [RK9; H, Ph], [RK10; H, Bn] , [RK11; H, CF 3 ], [RK 12; H, CF 3 CH 2 ], [RK 13; H, CF 3 CF 2 ], [RK 14; H, CF 2 H], [RK 15; H, CF 2 HCH 2 ], [RK16; Me, Me], [RK17; Me, Et], [RK18; Me, Pr], [RK19; Me, i-Pr], [RK20; Me, c-Pr], [RK21 Me, Bu], [RK22; Me, t-Bu], [RK23; Me, c-PrCH 2], [RK24; Me, Ph], [RK25; Me, Bn], [RK26; Me, CF 3], [ RK27; Me, CF 3 CH 2 ], [RK28; Me, CF 3 CF 2], [RK29; Me, CF 2 H], [RK30; Me, CF 2 HCH 2], [RK31; Et, Me], [RK 32; Et, Et], [RK 33; Et, Pr], [RK 34; Et, i-Pr], [RK 35; Et, c-Pr], [RK 36; Et, Bu], [RK 37; Et, t -Bu], [rK38; Et, c-PrCH 2], [RK39; Et, Ph], [RK40; Et, Bn], [RK41; Et, CF 3], [RK42; Et, CF 3 CH 2] , [RK 43; Et, CF 3 CF 2 ], [RK 44; Et, CF 2 H], [RK 45; Et, CF 2 HCH 2 ], [RK 46; Pr, Me], [RK 47; Pr, Et], [RK RK 48; Pr, Pr], [RK 49; Pr, i-Pr], [RK 50; Pr, c-Pr], [RK 51; Pr, Bu], [RK 52; Pr, t-Bu], [RK 53; Pr, c-PrCH 2 ], [RK 54; Pr, Ph], [RK 55; Pr, Bn], [RK 56; Pr, CF 3 ], [RK 57; Pr, CF 3 CH 2 ], [RK 58; Pr, CF 3 CF 2], [RK59; Pr, CF 2 H], [RK60; Pr, CF 2 HCH 2], [RK61; i-Pr, Me], [RK62; i-Pr, Et], [RK63 i-Pr, Pr], [RK64; i-Pr, i-Pr], [RK65; i-Pr, c-Pr], [RK66; i-Pr, Bu], [RK67; i-Pr, t -Bu], [RK68; i- Pr, c-PrCH 2], [RK69; i-Pr, Ph], [RK70; i-Pr, Bn], [RK71; i-Pr, CF 3], [RK72 ; i-Pr, CF 3 CH 2], [RK73; i-Pr, CF 3 CF 2], [RK74; i-Pr, CF 2 H], [RK75; i-Pr, CF 2 HCH 2], [ RK 76; c-Pr, Me], [RK 77; c-Pr, Et], [RK 78; c-Pr, Pr], [RK 79; c-Pr, i-Pr], [RK 80; c-Pr, c- Pr], [RK 81; c-Pr, Bu], [RK 82; c-Pr, t-Bu], [RK 83; c-Pr, c-PrCH 2 ], [RK 84; c-Pr, Ph], [RK 85 c-Pr, Bn], [RK 86; c-Pr, CF 3 ], [RK 87; c-Pr, CF 3 CH 2 ], [RK 88; c-Pr, CF 3 CF 2 ], [RK 89; c- Pr, CF 2 H], [ RK90; c-Pr, CF 2 HCH 2], [RK91; c-PrCH 2, Me], [RK92; c-PrCH 2, Et], [RK93; c-PrCH 2, Pr], [RK94; c- PrCH 2, i-Pr], [RK95; c-PrCH 2, c-Pr], [RK96; c-PrCH 2, Bu], [RK97; c-PrCH 2, t- Bu], [RK98; c- PrCH 2, c-PrCH 2], [RK99; c-PrCH 2, Ph], [RK100; c-PrCH 2, Bn], [RK101; c-PrCH 2, CF 3] , [RK102; c-PrCH 2 , CF 3 CH 2], [RK103; c-PrCH 2, CF 3 CF 2], [RK104; c-PrCH 2, CF 2 H], [RK105; c-PrCH 2, CF 2 HCH 2], [RK106 ; CF 3 CH 2, Me], [RK107; CF 3 CH 2, Et], [RK108; CF 3 CH 2, Pr], [RK109; CF 3 CH 2, i-Pr ], [RK110; CF 3 CH 2, c-Pr], [RK111; CF 3 CH 2, Bu], [RK112; C F 3 CH 2, t-Bu ], [RK113; CF 3 CH 2, c-PrCH 2], [RK114; CF 3 CH 2, Ph], [RK115; CF 3 CH 2, Bn], [RK116; CF 3 CH 2 , CF 3 ], [RK 117; CF 3 CH 2 , CF 3 CH 2 ], [RK 118; CF 3 CH 2 , CF 3 CF 2 ], [RK 119; CF 3 CH 2 , CF 2 H], [RK RK120; CF 3 CH 2, CF 2 HCH 2], [RK121; CF 2 HCH 2, Me], [RK122; CF 2 HCH 2, Et], [RK123; CF 2 HCH 2, Pr], [RK124; CF 2 HCH 2 , i-Pr], [RK 125; CF 2 HCH 2 , c-Pr], [RK 126; CF 2 HCH 2 , Bu], [RK 127; CF 2 HCH 2 , t-Bu], [RK 128; CF 2 HCH 2, c-PrCH 2 ], [RK129; CF 2 HCH 2, Ph], [RK130; CF 2 HCH 2, Bn], [RK131; CF 2 HCH 2, CF 3], [RK132; CF 2 HCH 2, CF 3 CH 2], [RK133; CF 2 HCH 2, CF 3 CF 2], [RK134; CF 2 HCH 2, CF 2 H], [RK135; CF 2 HCH 2, CF 2 HCH 2], [ RK136; MeOCH 2, Me], [RK137; MeOCH 2, Et], [RK138; MeOCH 2, Pr], [RK139; MeOCH 2, i-Pr], [RK140; MeOCH 2, c-Pr], [RK141 ; MeOCH 2, Bu], [ RK142; MeOCH 2, t-Bu], [RK143; MeOCH 2, c-PrCH 2], [RK144; MeOCH 2, Ph], [RK145; MeOCH 2, Bn], [RK146 ; MeOCH 2, CF 3], [RK147; MeOCH 2, CF 3 CH 2], [RK148; MeOCH 2, CF 3 CF 2], [RK149; MeOCH 2, CF 2 H], [RK150; MeOCH 2, CF 2 HCH 2 ], [RK 151; EtOCH 2 , Me], [RK 152; EtOCH 2 , Et], [RK153; EtOCH 2, Pr], [RK154; EtOCH 2, i-Pr], [RK155; EtOCH 2, c-Pr], [RK156; EtOCH 2, Bu], [RK157; EtOCH 2, t-Bu], [RK158; EtOCH 2, c-PrCH 2], [RK159; EtOCH 2, Ph], [RK160; EtOCH 2, Bn], [RK161; EtOCH 2, CF 3], [RK162; EtOCH 2 , CF 3 CH 2 ], [RK 163; EtOCH 2 , CF 3 CF 2 ], [RK 164; EtOCH 2 , CF 2 H], [RK 165; EtOCH 2 , CF 2 HCH 2 ], [RK 166; CH 2 CH 2 CH 2], [RK167; CH 2 CH 2 CH 2 CH 2], [RK168; t-Bu, Me], [RK169; t-Bu, Et], [RK170; t-Bu, Pr], [RK171; t -Bu, i-Pr], [RK172; t-Bu, c-Pr], [RK173; t-Bu, t-Bu], [RK174; t-Bu, Bu], [RK175; t-Bu, t -Bu], [RK176; t- Bu, c-PrCH 2], [RK177; t-Bu, Ph], [RK178; t-Bu, Bn], [RK179; t-Bu, CF 3], [RK180 t-Bu, CF 3 CH 2 ], [RK 181; t-Bu, CF 3 CF 2 ], [RK 182; t-Bu, CF 2 H], [RK 183; t-Bu, CF 2 HCH 2 ], [RK RK 184; i-Bu, Me], [RK 185; i-Bu, Et], [RK 186; i-Bu, Pr], [RK 187; i-Bu, i-Pr], [RK 188; i-Bu, c- Pr], [RK189; i-Bu, t-Bu], [RK190; i-Bu, Bu], [RK191; i-Bu, t-Bu], [RK192; i-Bu, c-PrCH 2 ], [RK193; i-Bu, Ph ], [RK194; i-Bu, Bn], [RK195; i-Bu, CF 3], [RK196; i-Bu, CF 3 CH 2], [RK197; i-Bu , CF 3 CF 2 ], [RK 198; i-Bu, CF 2 H], [RK 199: i-Bu, CF 2 HCH 2 ], [RK 200; HCCCH 2 , Me], [RK 201; HCC CH 2, Et], [RK202 ; HCCCH 2, Pr], [RK203; HCCCH 2, i-Pr], [RK204; HCCCH 2, c-Pr], [RK205; HCCCH 2, t-Bu], [RK206 ; HCCCH 2, Bu], [ RK207; HCCCH 2, t-Bu], [RK208; HCCCH 2, c-PrCH 2], [RK209; HCCCH 2, Ph], [RK210; HCCCH 2, Bn], [RK211 ; HCCCH 2, CF 3], [RK212; HCCCH 2, CF 3 CH 2], [RK213; HCCCH 2, CF 3 CF 2], [RK214; HCCCH 2, CF 2 H], [RK215; HCCCH 2, CF 2 HCH 2], [RK216; MeCCCH 2, Me], [RK217; MeCCCH 2, Et], [RK218; MeCCCH 2, Pr], [RK219; MeCCCH 2, i-Pr], [RK220; MeCCCH 2, c -Pr], [RK221; MeCCCH 2 , t-Bu], [RK222; MeCCCH 2, Bu], [RK223; MeCCCH 2, t-Bu], [RK224; MeCCCH 2, c-PrCH 2], [RK225; MeCCCH 2, Ph], [RK226 ; MeCCCH 2, Bn], [RK227; MeCCCH 2, CF 3], [RK228; MeCCCH 2, CF 3 CH 2], [RK229; MeCCCH 2, CF 3 CF 2], [ RK230; MeCCCH 2, CF 2 H ], [RK231; MeCCCH 2, CF 2 HCH 2], [RK232; MeSCH 2, Me], [RK233; MeSCH 2, Et], [RK234; MeSCH 2, Pr], [ RK235; MeSCH 2, i-Pr ], [RK236; MeSCH 2, c-Pr], [RK237; MeSCH 2, t-Bu], [RK238; MeSCH 2, Bu], [RK239; MeSCH 2, t-Bu ], [RK240; MeSCH 2, c-PrCH 2], [RK241; MeSCH 2, Ph], [RK242; MeSCH 2, Bn], [RK243; MeSCH 2, CF 3], [RK244; MeSCH 2, CF 3 C H 2], [RK245; MeSCH 2, CF 3 CF 2], [RK246; MeSCH 2, CF 2 H], [RK247; MeSCH 2, CF 2 HCH 2], [RK248; EtSCH 2, Me], [RK249 EtSCH 2 , Et], [RK 250; EtSCH 2 , Pr],

[RK251;EtSCH2,i-Pr],[RK252;EtSCH2,c-Pr],[RK253;EtSCH2,t-Bu],[RK254;EtSCH2,Bu],[RK255;EtSCH2,t-Bu],[RK256;EtSCH2,c-PrCH2],[RK257;EtSCH2,Ph],[RK258;EtSCH2,Bn],[RK259;EtSCH2,CF3],[RK260;EtSCH2,CF3CH2],[RK261;EtSCH2,CF3CF2],[RK262;EtSCH2,CF2H],[RK263;EtSCH2,CF2HCH2],[RK264;2-Me-Ph,Me],[RK265;2-Me-Ph,Et],[RK266;2-Me-Ph,Pr],[RK267;2-Me-Ph,i-Pr],[RK268;2-Me-Ph,c-Pr],[RK269;2-Me-Ph,t-Bu],[RK270;2-Me-Ph,Bu],[RK271;2-Me-Ph,t-Bu],[RK272;2-Me-Ph,c-PrCH2],[RK273;2-Me-Ph,Ph],[RK274;2-Me-Ph,Bn],[RK275;2-Me-Ph,CF3],[RK276;2-Me-Ph,CF3CH2],[RK277;2-Me-Ph,CF3CF2],[RK278;2-Me-Ph,CF2H],[RK279;2-Me-Ph,CF2HCH2],[RK280;3-Me-Ph,Me],[RK281;3-Me-Ph,Et],[RK282;3-Me-Ph,Pr],[RK283;3-Me-Ph,i-Pr],[RK284;3-Me-Ph,c-Pr],[RK285;3-Me-Ph,t-Bu],[RK286;3-Me-Ph,Bu],[RK287;3-Me-Ph,t-Bu],[RK288;3-Me-Ph,c-PrCH2],[RK289;3-Me-Ph,Ph],[RK290;3-Me-Ph,Bn],[RK291;3-Me-Ph,CF3],[RK292;3-Me-Ph,CF3CH2],[RK293;3-Me-Ph,CF3CF2],[RK294;3-Me-Ph,CF2H],[RK295;3-Me-Ph,CF2HCH2],[RK296;4-Me-Ph,Me],[RK297;4-Me-Ph,Et],[RK298;4-Me-Ph,Pr],[RK299;4-Me-Ph,i-Pr],[RK300;4-Me-Ph,c-Pr],[RK301;4-Me-Ph,t-Bu],[RK302;4-Me-Ph,Bu],[RK303;4-Me-Ph,t-Bu],[RK304;4-Me-Ph,c-PrCH2],[RK305;4-Me-Ph,Ph],[RK306;4-Me-Ph,Bn],[RK307;4-Me-Ph,CF3],[RK308;4-Me-Ph,CF3CH2],[RK309;4-Me-Ph,CF3CF2],[RK310;4-Me-Ph,CF2H],[RK311;4-Me-Ph,CF2HCH2],[RK312;2-F-Ph,Me],[RK313;2-F-Ph,Et],[RK314;2-F-Ph,Pr],[RK315;2-F-Ph,i-Pr],[RK316;2-F-Ph,c-Pr],[RK317;2-F-Ph,t-Bu],[RK318;2-F-Ph,Bu],[RK319;2-F-Ph,t-Bu],[RK320;2-F-Ph,c-PrCH2],[RK321;2-F-Ph,Ph],[RK322;2-F-Ph,Bn],[RK323;2-F-Ph,CF3],[RK324;2-F-Ph,CF3CH2],[RK325;2-F-Ph,CF3CF2],[RK326;2-F-Ph,CF2H],[RK327;2-F-Ph,CF2HCH2],[RK328;3-F-Ph,Me],[RK329;3-F-Ph,Et],[RK330;3-F-Ph,Pr],[RK331;3-F-Ph,i-Pr],[RK332;3-F-Ph,c-Pr],[RK333;3-F-Ph,t-Bu],[RK334;3-F-Ph,Bu],[RK335;3-F-Ph,t-Bu],[RK336;3-F-Ph,c-PrCH2],[RK337;3-F-Ph,Ph],[RK338;3-F-Ph,Bn],[RK339;3-F-Ph,CF3],[RK340;3-F-Ph,CF3CH2],[RK341;3-F-Ph,CF3CF2],[RK342;3-F-Ph,CF2H],[RK343;3-F-Ph,CF2HCH2],[RK344;4-F-Ph,Me],[RK345;4-F-Ph,Et],[RK346;4-F-Ph,Pr],[RK347;4-F-Ph,i-Pr],[RK348;4-F-Ph,c-Pr],[RK349;4-F-Ph,t-Bu],[RK350;4-F-Ph,Bu],[RK351;4-F-Ph,t-Bu],[RK352;4-F-Ph,c-PrCH2],[RK353;4-F-Ph,Ph],[RK354;4-F-Ph,Bn],[RK355;4-F-Ph,CF3],[RK356;4-F-Ph,CF3CH2],[RK357;4-F-Ph,CF3CF2],[RK358;4-F-Ph,CF2H],[RK359;4-F-Ph,CF2HCH2],[RK360;2-MeO-Ph,Me],[RK361;2-MeO-Ph,Et],[RK362;2-MeO-Ph,Pr],[RK363;2-MeO-Ph,i-Pr],[RK364;2-MeO-Ph,c-Pr],[RK365;2-MeO-Ph,t-Bu],[RK366;2-MeO-Ph,Bu],[RK367;2-MeO-Ph,t-Bu],[RK368;2-MeO-Ph,c-PrCH2],[RK369;2-MeO-Ph,Ph],[RK370;2-MeO-Ph,Bn],[RK371;2-MeO-Ph,CF3],[RK372;2-MeO-Ph,CF3CH2],[RK373;2-MeO-Ph,CF3CF2],[RK374;2-MeO-Ph,CF2H],[RK375;2-MeO-Ph,CF2HCH2],[RK376;3-MeO-Ph,Me],[RK377;3-MeO-Ph,Et],[RK378;3-MeO-Ph,Pr],[RK379;3-MeO-Ph,i-Pr],[RK380;3-MeO-Ph,c-Pr],[RK381;3-MeO-Ph,t-Bu],[RK382;3-MeO-Ph,Bu],[RK383;3-MeO-Ph,t-Bu],[RK384;3-MeO-Ph,c-PrCH2],[RK385;3-MeO-Ph,Ph],[RK386;3-MeO-Ph,Bn],[RK387;3-MeO-Ph,CF3],[RK388;3-MeO-Ph,CF3CH2],[RK389;3-MeO-Ph,CF3CF2],[RK390;3-MeO-Ph,CF2H],[RK391;3-MeO-Ph,CF2HCH2],[RK392;4-MeO-Ph,Me],[RK393;4-MeO-Ph,Et],[RK394;4-MeO-Ph,Pr],[RK395;4-MeO-Ph,i-Pr],[RK396;4-MeO-Ph,c-Pr],[RK397;4-MeO-Ph,t-Bu],[RK398;4-MeO-Ph,Bu],[RK399;4-MeO-Ph,t-Bu],[RK400;4-MeO-Ph,c-PrCH2],[RK401;4-MeO-Ph,Ph],[RK402;4-MeO-Ph,Bn],[RK403;4-MeO-Ph,CF3],[RK404;4-MeO-Ph,CF3CH2],[RK405;4-MeO-Ph,CF3CF2],[RK406;4-MeO-Ph,CF2H],[RK407;4-MeO-Ph,CF2HCH2]
[RK251; EtSCH 2 , i-Pr], [RK 252; EtSCH 2 , c-Pr], [RK 253; EtSCH 2 , t-Bu], [RK 254; EtSCH 2 , Bu], [RK 255; EtSCH 2 , t- Bu], [RK256; EtSCH 2 , c-PrCH 2], [RK257; EtSCH 2, Ph], [RK258; EtSCH 2, Bn], [RK259; EtSCH 2, CF 3], [RK260; EtSCH 2, CF 3 CH 2], [RK261; EtSCH 2, CF 3 CF 2], [RK262; EtSCH 2, CF 2 H], [RK263; EtSCH 2, CF 2 HCH 2], [RK264; 2-Me-Ph, Me ], [RK265; 2-Me-Ph, Et], [RK266; 2-Me-Ph, Pr], [RK267; 2-Me-Ph, i-Pr], [RK268; 2-Me-Ph, c] -Pr], [RK 269; 2-Me-Ph, t-Bu], [RK 270; 2-Me-Ph, Bu], [RK 271; 2-Me-Ph, t-Bu], [RK 272; -Ph, c-PrCH 2], [RK273; 2-Me-Ph, Ph], [RK274; 2-Me-Ph, Bn], [RK275; 2-Me-Ph, CF 3], [RK276; 2 -Me-Ph, CF 3 CH 2 ], [RK277; 2-Me-Ph, CF 3 CF 2], [RK278; 2-Me-Ph, CF 2 H], [RK279; 2-Me-Ph, CF 2 HCH 2 ], [RK 280; 3-Me-Ph, Me], [RK 281; 3-Me-Ph, Et], [RK 282, 3-Me-Ph, Pr], [RK 283; 3-Me-Ph, i-Pr], [RK284; 3-Me-Ph, c-Pr], [RK 285; 3-Me-Ph, t-Bu], [RK 286; 3-Me-Ph, Bu], [RK 287; Me-Ph, t-Bu] , [RK288; 3-Me-Ph, c-PrCH 2], [RK289; 3-Me-Ph, Ph], [RK290; 3-Me-Ph, Bn], [RK291 ; 3-Me-Ph, CF 3], [RK292; 3-Me-Ph, CF 3 CH 2], [RK293; 3-Me-Ph, CF 3 CF 2], [RK294; 3-Me-Ph, CF 2 H], [RK 295; 3-Me-Ph, CF 2 HCH 2], [RK296; 4 -Me-Ph, Me], [RK297; 4-Me-Ph, Et], [RK298; 4-Me-Ph, Pr], [RK299; 4-Me-Ph, i -Pr], [RK300; 4-Me-Ph, c-Pr], [RK301; 4-Me-Ph, t-Bu], [RK302; 4-Me-Ph, Bu], [RK303; -Ph, t-Bu], [ RK304; 4-Me-Ph, c-PrCH 2], [RK305; 4-Me-Ph, Ph], [RK306; 4-Me-Ph, Bn], [RK307; 4-Me-Ph, CF 3 ], [RK308; 4-Me-Ph, CF 3 CH 2], [RK309; 4-Me-Ph, CF 3 CF 2], [RK310; 4-Me-Ph, CF 2 H], [RK 311; 4-Me-Ph, CF 2 HCH 2 ], [RK 312; 2-F-Ph, Me], [RK 313; 2-F-Ph, Et], [RK 314; 2-F- Ph, Pr], [RK315; 2-F-Ph, i-Pr], [RK316; 2-F-Ph, c-Pr], [RK317; 2-F-Ph, t-Bu], [RK318; 2-F-Ph, Bu], [RK 319; 2-F-Ph, t-Bu], [RK 320; 2-F-Ph, c-PrCH 2 ], [RK 321; 2-F-Ph, Ph], [RK322; 2-F-Ph , Bn], [RK323; 2-F-Ph, CF 3], [RK324; 2-F-Ph, CF 3 CH 2], [RK325; 2-F-Ph, CF 3 CF 2], [RK326; 2-F-Ph, CF 2 H], [RK327; 2-F-Ph, CF 2 HCH 2], [RK328; 3-F-Ph, Me], [RK329; 3 -F-Ph, Et], [RK330; 3-F-Ph, Pr], [RK331; 3-F-Ph, i-Pr], [RK332; 3-F-Ph, c-Pr], [RK333] 3-F-Ph, t-Bu], [RK334; 3-F-Ph, Bu], [RK335; 3-F-Ph, t-Bu], [RK336; 3-F-Ph, c-PrCH] 2 ], [RK 337; 3-F-Ph, Ph], [RK 338; 3-F-Ph, Bn], [RK 339; 3-F-Ph, CF 3 ], [RK 340; 3-F-Ph, CF] 3 CH 2 ], [RK 341; 3-F-Ph, CF 3 CF 2 ], [RK 342; 3-F-Ph, CF 2 H], [RK343; 3- F-Ph, CF 2 HCH 2], [RK344; 4-F-Ph, Me], [RK345; 4-F-Ph, Et], [RK346; 4-F-Ph , Pr], [RK 347; 4-F-Ph, i-Pr], [RK 348; 4-F-Ph, c-Pr], [RK 349; 4-F-Ph, t-Bu], [RK 350; -F-Ph, Bu], [RK 351; 4-F-Ph, t-Bu], [RK 352; 4-F-Ph, c-PrCH 2 ], [RK 353; 4-F-Ph, Ph], [RK] RK 354; 4-F-Ph, Bn], [RK 355; 4-F-Ph, CF 3 ], [RK 356; 4-F-Ph, CF 3 CH 2 ], [RK 357; 4-F-Ph, CF 3 CF 2], [RK358; 4 -F-Ph, CF 2 H], [RK359; 4-F-Ph, CF 2 HCH 2], [RK360; 2-MeO-Ph, Me], [RK361; 2- MeO-Ph, Et], [RK362; 2-MeO-Ph, Pr], [RK363; 2-MeO-Ph, i-Pr], [RK364; 2-MeO-Ph, c-Pr], [RK365; 2-MeO-Ph, t-Bu], [RK 366; 2-MeO-Ph, Bu], [RK 367; 2-MeO-Ph, t-Bu], [RK 368; 2-MeO-Ph, c-PrCH 2 ], [RK369; 2-MeO -Ph, Ph], [RK370; 2-MeO-Ph, Bn], [RK371; 2-MeO-Ph, CF 3], [RK372; 2-MeO-Ph, CF 3 CH 2], [RK373; 2 -MeO-Ph, CF 3 CF 2], [RK374; 2-MeO-Ph, CF 2 H], [RK375; 2-MeO-Ph, CF 2 HCH 2], [RK376 3-MeO-Ph, Me], [RK377; 3-MeO-Ph, Et], [RK378; 3-MeO-Ph, Pr], [RK379; 3-MeO-Ph, i-Pr], [RK380] 3-MeO-Ph, c-Pr], [RK 381; 3-MeO-Ph, t-Bu], [RK 382; 3-MeO-Ph, Bu], [RK 383; 3-MeO-Ph, t-Bu ], [RK 384; 3-MeO-Ph, c-PrCH 2 ], [RK 385; 3-MeO-Ph, Ph], [RK 386; 3-MeO-Ph, Bn], [RK 387; 3-MeO-Ph, CF 3 ], [RK 388; 3-M eO-Ph, CF 3 CH 2 ], [RK389; 3-MeO-Ph, CF 3 CF 2], [RK390; 3-MeO-Ph, CF 2 H], [RK391; 3-MeO-Ph, CF 2 HCH 2], [RK392; 4 -MeO-Ph, Me], [RK393; 4-MeO-Ph, Et], [RK394; 4-MeO-Ph, Pr], [RK395; 4-MeO-Ph, i -Pr], [RK396; 4-MeO-Ph, c-Pr], [RK 397; 4-MeO-Ph, t-Bu], [RK 398; 4-MeO-Ph, Bu], [RK 399; 4-MeO -Ph, t-Bu], [ RK400; 4-MeO-Ph, c-PrCH 2], [RK401; 4-MeO-Ph, Ph], [RK402; 4-MeO-Ph, Bn], [RK403; 4-MeO-Ph, CF 3 ], [RK404; 4-MeO-Ph, CF 3 CH 2], [RK405; 4-MeO-Ph, CF 3 CF 2], [RK406; 4-MeO-Ph, CF 2 H], [RK 407; 4-MeO-Ph, CF 2 HCH 2 ]

式(XIII)

Figure 2019089711
〔式中、R25及びR31は上記と同じ意味を表す。〕
で表される化合物において、R31及びR25の組合わせが下記に示される置換基番号RL1〜RL407のいずれかに記載の組合わせである化合物(以下、置換基番号RL1〜RL407の化合物を本発明化合物RL1〜RL407と表し、本発明化合物RL1〜RL407をまとめて本発明化合物RLと表す)は、上記の製造法に記載の方法に準じて得ることができる。
なお、置換基番号RL1〜RL407とは、式(XIII)で表される化合物における、R31及びR25の組合せを表すものであり、以下、[置換基番号;R31,R25]と記す。ただし、置換基番号RL166及びRL167においては、R31とR25とが、互いに結合してヘテロ環を形成することを表す。
例えば、置換基番号RL4とは、R31が水素原子であり、R25がイソプロピル基である組合せを表す。 Formula (XIII)
Figure 2019089711
[Wherein, R 25 and R 31 represent the same meaning as described above. ]
Wherein the combination of R 31 and R 25 is a combination as set forth in any of Substituent Nos. RL 1 to RL 407 shown below (hereinafter referred to as “compound of Substituent Nos. RL 1 to RL 407” Invention compounds RL1 to RL407, and the invention compounds RL1 to RL407 are collectively referred to as the invention compound RL) can be obtained according to the method described in the above-mentioned production method.
The substituent numbers RL1 to RL407 represent a combination of R 31 and R 25 in the compound represented by the formula (XIII), and hereinafter referred to as [substituent number: R 31 , R 25 ]. . However, in Substituent Nos. RL166 and RL167, R 31 and R 25 represent that they combine with each other to form a heterocycle.
For example, the substituent number RL4 represents a combination in which R 31 is a hydrogen atom and R 25 is an isopropyl group.

例えば、本発明化合物RL4とは、式(XIII)で表される化合物において置換基番号がRL4である化合物を意味し、式(XIII)で表される化合物において、R31が水素原子であり、R25がイソプロピル基である下記の化合物を表す。

Figure 2019089711
For example, the compound of the present invention RL4 means a compound represented by the formula (XIII) in which the substituent number is RL4, and in the compound represented by the formula (XIII), R 31 is a hydrogen atom, Represents the following compound wherein R 25 is an isopropyl group.
Figure 2019089711

[置換基番号;R31,R25]:[RL1;H,Me],[RL2;H,Et],[RL3;H,Pr],[RL4;H,i-Pr],[RL5;H,c-Pr],[RL6;H,Bu],[RL7;H,t-Bu],[RL8;H,c-PrCH2],[RL9;H,Ph],[RL10;H,Bn],[RL11;H,CF3],[RL12;H,CF3CH2],[RL13;H,CF3CF2],[RL14;H,CF2H],[RL15;H,CF2HCH2],[RL16;Me,Me],[RL17;Me,Et],[RL18;Me,Pr],[RL19;Me,i-Pr],[RL20;Me,c-Pr],[RL21Me,Bu],[RL22;Me,t-Bu],[RL23;Me,c-PrCH2],[RL24;Me,Ph],[RL25;Me,Bn],[RL26;Me,CF3],[RL27;Me,CF3CH2],[RL28;Me,CF3CF2],[RL29;Me,CF2H],[RL30;Me,CF2HCH2],[RL31;Et,Me],[RL32;Et,Et],[RL33;Et,Pr],[RL34;Et,i-Pr],[RL35;Et,c-Pr],[RL36;Et,Bu],[RL37;Et,t-Bu],[RL38;Et,c-PrCH2],[RL39;Et,Ph],[RL40;Et,Bn],[RL41;Et,CF3],[RL42;Et,CF3CH2],[RL43;Et,CF3CF2],[RL44;Et,CF2H],[RL45;Et,CF2HCH2],[RL46;Pr,Me],[RL47;Pr,Et],[RL48;Pr,Pr],[RL49;Pr,i-Pr],[RL50;Pr,c-Pr],[RL51;Pr,Bu],[RL52;Pr,t-Bu],[RL53;Pr,c-PrCH2],[RL54;Pr,Ph],[RL55;Pr,Bn],[RL56;Pr,CF3],[RL57;Pr,CF3CH2],[RL58;Pr,CF3CF2],[RL59;Pr,CF2H],[RL60;Pr,CF2HCH2],[RL61;i-Pr,Me],[RL62;i-Pr,Et],[RL63;i-Pr,Pr],[RL64;i-Pr,i-Pr],[RL65;i-Pr,c-Pr],[RL66;i-Pr,Bu],[RL67;i-Pr,t-Bu],[RL68;i-Pr,c-PrCH2],[RL69;i-Pr,Ph],[RL70;i-Pr,Bn],[RL71;i-Pr,CF3],[RL72;i-Pr,CF3CH2],[RL73;i-Pr,CF3CF2],[RL74;i-Pr,CF2H],[RL75;i-Pr,CF2HCH2],[RL76;c-Pr,Me],[RL77;c-Pr,Et],[RL78;c-Pr,Pr],[RL79;c-Pr,i-Pr],[RL80;c-Pr,c-Pr],[RL81;c-Pr,Bu],[RL82;c-Pr,t-Bu],[RL83;c-Pr,c-PrCH2],[RL84;c-Pr,Ph],[RL85;c-Pr,Bn],[RL86;c-Pr,CF3],[RL87;c-Pr,CF3CH2],[RL88;c-Pr,CF3CF2],[RL89;c-Pr,CF2H],[RL90;c-Pr,CF2HCH2],[RL91;c-PrCH2,Me],[RL92;c-PrCH2,Et],[RL93;c-PrCH2,Pr],[RL94;c-PrCH2,i-Pr],[RL95;c-PrCH2,c-Pr],[RL96;c-PrCH2,Bu],[RL97;c-PrCH2,t-Bu],[RL98;c-PrCH2,c-PrCH2],[RL99;c-PrCH2,Ph],[RL100;c-PrCH2,Bn],[RL101;c-PrCH2,CF3],[RL102;c-PrCH2,CF3CH2],[RL103;c-PrCH2,CF3CF2],[RL104;c-PrCH2,CF2H],[RL105;c-PrCH2,CF2HCH2],[RL106;CF3CH2,Me],[RL107;CF3CH2,Et],[RL108;CF3CH2,Pr],[RL109;CF3CH2,i-Pr],[RL110;CF3CH2,c-Pr],[RL111;CF3CH2,Bu],[RL112;CF3CH2,t-Bu],[RL113;CF3CH2,c-PrCH2],[RL114;CF3CH2,Ph],[RL115;CF3CH2,Bn],[RL116;CF3CH2,CF3],[RL117;CF3CH2,CF3CH2],[RL118;CF3CH2,CF3CF2],[RL119;CF3CH2,CF2H],[RL120;CF3CH2,CF2HCH2],[RL121;CF2HCH2,Me],[RL122;CF2HCH2,Et],[RL123;CF2HCH2,Pr],[RL124;CF2HCH2,i-Pr],[RL125;CF2HCH2,c-Pr],[RL126;CF2HCH2,Bu],[RL127;CF2HCH2,t-Bu],[RL128;CF2HCH2,c-PrCH2],[RL129;CF2HCH2,Ph],[RL130;CF2HCH2,Bn],[RL131;CF2HCH2,CF3],[RL132;CF2HCH2,CF3CH2],[RL133;CF2HCH2,CF3CF2],[RL134;CF2HCH2,CF2H],[RL135;CF2HCH2,CF2HCH2],[RL136;MeOCH2,Me],[RL137;MeOCH2,Et],[RL138;MeOCH2,Pr],[RL139;MeOCH2,i-Pr],[RL140;MeOCH2,c-Pr],[RL141;MeOCH2,Bu],[RL142;MeOCH2,t-Bu],[RL143;MeOCH2,c-PrCH2],[RL144;MeOCH2,Ph],[RL145;MeOCH2,Bn],[RL146;MeOCH2,CF3],[RL147;MeOCH2,CF3CH2],[RL148;MeOCH2,CF3CF2],[RL149;MeOCH2,CF2H],[RL150;MeOCH2,CF2HCH2],[RL151;EtOCH2,Me],[RL152;EtOCH2,Et],[RL153;EtOCH2,Pr],[RL154;EtOCH2,i-Pr],[RL155;EtOCH2,c-Pr],[RL156;EtOCH2,Bu],[RL157;EtOCH2,t-Bu],[RL158;EtOCH2,c-PrCH2],[RL159;EtOCH2,Ph],[RL160;EtOCH2,Bn],[RL161;EtOCH2,CF3],[RL162;EtOCH2,CF3CH2],[RL163;EtOCH2,CF3CF2],[RL164;EtOCH2,CF2H],[RL165;EtOCH2,CF2HCH2],[RL166;CH2CH2CH2],[RL167;CH2CH2CH2CH2],[RL168;t-Bu,Me],[RL169;t-Bu,Et],[RL170;t-Bu,Pr],[RL171;t-Bu,i-Pr],[RL172;t-Bu,c-Pr],[RL173;t-Bu,t-Bu],[RL174;t-Bu,Bu],[RL175;t-Bu,t-Bu],[RL176;t-Bu,c-PrCH2],[RL177;t-Bu,Ph],[RL178;t-Bu,Bn],[RL179;t-Bu,CF3],[RL180;t-Bu,CF3CH2],[RL181;t-Bu,CF3CF2],[RL182;t-Bu,CF2H],[RL183;t-Bu,CF2HCH2],[RL184;i-Bu,Me],[RL185;i-Bu,Et],[RL186;i-Bu,Pr],[RL187;i-Bu,i-Pr],[RL188;i-Bu,c-Pr],[RL189;i-Bu,t-Bu],[RL190;i-Bu,Bu],[RL191;i-Bu,t-Bu],[RL192;i-Bu,c-PrCH2],[RL193;i-Bu,Ph],[RL194;i-Bu,Bn],[RL195;i-Bu,CF3],[RL196;i-Bu,CF3CH2],[RL197;i-Bu,CF3CF2],[RL198;i-Bu,CF2H],[RL199;i-Bu,CF2HCH2],[RL200;HCCCH2,Me],[RL201;HCCCH2,Et],[RL202;HCCCH2,Pr],[RL203;HCCCH2,i-Pr],[RL204;HCCCH2,c-Pr],[RL205;HCCCH2,t-Bu],[RL206;HCCCH2,Bu],[RL207;HCCCH2,t-Bu],[RL208;HCCCH2,c-PrCH2],[RL209;HCCCH2,Ph],[RL210;HCCCH2,Bn],[RL211;HCCCH2,CF3],[RL212;HCCCH2,CF3CH2],[RL213;HCCCH2,CF3CF2],[RL214;HCCCH2,CF2H],[RL215;HCCCH2,CF2HCH2],[RL216;MeCCCH2,Me],[RL217;MeCCCH2,Et],[RL218;MeCCCH2,Pr],[RL219;MeCCCH2,i-Pr],[RL220;MeCCCH2,c-Pr],[RL221;MeCCCH2,t-Bu],[RL222;MeCCCH2,Bu],[RL223;MeCCCH2,t-Bu],[RL224;MeCCCH2,c-PrCH2],[RL225;MeCCCH2,Ph],[RL226;MeCCCH2,Bn],[RL227;MeCCCH2,CF3],[RL228;MeCCCH2,CF3CH2],[RL229;MeCCCH2,CF3CF2],[RL230;MeCCCH2,CF2H],[RL231;MeCCCH2,CF2HCH2],[RL232;MeSCH2,Me],[RL233;MeSCH2,Et],[RL234;MeSCH2,Pr],[RL235;MeSCH2,i-Pr],[RL236;MeSCH2,c-Pr],[RL237;MeSCH2,t-Bu],[RL238;MeSCH2,Bu],[RL239;MeSCH2,t-Bu],[RL240;MeSCH2,c-PrCH2],[RL241;MeSCH2,Ph],[RL242;MeSCH2,Bn],[RL243;MeSCH2,CF3],[RL244;MeSCH2,CF3CH2],[RL245;MeSCH2,CF3CF2],[RL246;MeSCH2,CF2H],[RL247;MeSCH2,CF2HCH2],[RL248;EtSCH2,Me],[RL249;EtSCH2,Et],[RL250;EtSCH2,Pr], [Substituent number; R 31 , R 25 ]: [RL 1; H, Me], [RL 2; H, Et], [RL 3; H, Pr], [RL 4; H, i-Pr], [RL 5; , c-Pr], [RL 6; H, Bu], [RL 7; H, t-Bu], [RL 8; H, c-PrCH 2 ], [RL 9; H, Ph], [RL 10; H, Bn] , [RL 11; H, CF 3 ], [RL 12; H, CF 3 CH 2 ], [RL 13; H, CF 3 CF 2 ], [RL 14; H, CF 2 H], [RL 15; H, CF 2 HCH 2 ], [RL 16; Me, Me], [RL 17; Me, Et], [RL 18; Me, Pr], [RL 19; Me, i-Pr], [RL 20; Me, c-Pr], [RL 21 Me, [RL 21 Me, Bu], [RL 22; Me, t-Bu], [RL 23; Me, c-PrCH 2 ], [RL 24; Me, Ph], [RL 25; Me, Bn], [RL 26; Me, CF 3 ], [[ RL27; Me, CF 3 CH 2 ], [RL28; Me, CF 3 CF 2], [RL29; Me, CF 2 H], [RL30; Me, CF 2 HCH 2], [RL31; Et, Me], [RL 32; Et, Et], [RL 33; Et, Pr], [RL 34; Et, i-Pr], [RL 35; Et, c-Pr], [RL 36; Et, Bu], [RL 37; Et, t -Bu], [RL 38; Et, c-PrCH 2 ], [RL 39; Et, Ph], [RL 40; Et, Bn], [RL 41; Et, CF 3 ], [RL 42; Et, CF 3 CH 2 ] , [RL 43; Et, CF 3 CF 2 ], [RL 44; Et, CF 2 H], [RL 45; Et, CF 2 HCH 2 ], [RL 46; Pr, Me], [RL 47; Pr, Et], [RL RL 48; Pr, Pr], [RL 49; Pr, i-Pr], [RL 50; Pr, c-Pr], [RL 51; Pr, Bu], [RL 52; Pr, t-Bu], [RL 53; Pr, c-PrCH 2 ], [RL 54; Pr, Ph], [RL 55; Pr, Bn], [RL 56; Pr, CF 3 ], [RL 57; Pr, CF 3 CH 2 ], [RL 58; Pr, CF 3 CF 2 ], [RL 59; Pr, CF 2 H], [RL 60; Pr, CF 2 HCH 2 ], [RL 61; i-Pr, Me], [RL 62; i-Pr, Et], [RL 63] i-Pr, Pr], [RL 64; i-Pr, i-Pr], [RL 65; i-Pr, c-Pr], [RL 66; i-Pr, Bu], [RL 67; i-Pr, t -Bu], [RL 68; i-Pr, c-PrCH 2 ], [RL 69; i-Pr, Ph], [RL 70; i-Pr, Bn], [RL 71; i-Pr, CF 3 ], [RL 72 i-Pr, CF 3 CH 2 ], [RL 73; i-Pr, CF 3 CF 2 ], [RL 74; i-Pr, CF 2 H], [RL 75; i-Pr, CF 2 HCH 2 ], [RL 75; RL 76; c-Pr, Me], [RL 77; c-Pr, Et], [RL 78; c-Pr, Pr], [RL 79; c-Pr, i-Pr], [RL 80; c-Pr, c- Pr], [RL 81; c-Pr, Bu], [RL 82; c-Pr, t-Bu], [RL 83; c-Pr, c-PrCH 2 ], [RL 84; c-Pr, Ph], [RL 85 c-Pr, Bn], [RL 86; c-Pr, CF 3 ], [RL 87; c-Pr, CF 3 CH 2 ], [RL 88; c-Pr, CF 3 CF 2 ], [RL 89; c- Pr, CF 2 H], [ RL90; c-Pr, CF 2 HCH 2], [RL91; c-PrCH 2, Me], [RL92; c-PrCH 2, Et], [RL93; c-PrCH 2, Pr], [RL94; c- PrCH 2, i-Pr], [RL95; c-PrCH 2, c-Pr], [RL96; c-PrCH 2, Bu], [RL97; c-PrCH 2, t- Bu], [RL 98; c-PrCH 2 , c-PrCH 2 ], [RL 99; c-PrCH 2 , Ph], [RL 100; c-PrCH 2 , Bn], [RL 101; c-PrCH 2 , CF 3 ] , [RL102; c-PrCH 2 , CF 3 CH 2], [RL103; c-PrCH 2, CF 3 CF 2], [RL104; c-PrCH 2, CF 2 H], [RL105; c-PrCH 2, CF 2 HCH 2 ], [RL 106; CF 3 CH 2 , Me], [RL 107; CF 3 CH 2 , Et], [RL 108; CF 3 CH 2 , Pr], [RL 109; CF 3 CH 2 , i-Pr ], [RL 110; CF 3 CH 2 , c-Pr], [RL 111; CF 3 CH 2 , Bu], [RL 112; C] F 3 CH 2, t-Bu ], [RL113; CF 3 CH 2, c-PrCH 2], [RL114; CF 3 CH 2, Ph], [RL115; CF 3 CH 2, Bn], [RL116; CF 3 CH 2 , CF 3 ], [RL 117; CF 3 CH 2 , CF 3 CH 2 ], [RL 118; CF 3 CH 2 , CF 3 CF 2 ], [RL 119; CF 3 CH 2 , CF 2 H], [RL RL120; CF 3 CH 2, CF 2 HCH 2], [RL121; CF 2 HCH 2, Me], [RL122; CF 2 HCH 2, Et], [RL123; CF 2 HCH 2, Pr], [RL124; CF 2 HCH 2 , i-Pr], [RL 125; CF 2 HCH 2 , c-Pr], [RL 126; CF 2 HCH 2 , Bu], [RL 127; CF 2 HCH 2 , t-Bu], [RL 128; CF 2 HCH 2 , c-PrCH 2 ], [RL 129; CF 2 HCH 2 , Ph], [RL 130; CF 2 HCH 2 , Bn], [RL 131; CF 2 HCH 2 , CF 3 ], [RL 132; CF 2 HCH 2, CF 3 CH 2], [RL133; CF 2 HCH 2, CF 3 CF 2], [RL134; CF 2 HCH 2, CF 2 H], [RL135; CF 2 HCH 2, CF 2 HCH 2], [ RL136; MeOCH 2, Me], [RL137; MeOCH 2, Et], [RL138; MeOCH 2, Pr], [RL139; MeOCH 2, i-Pr], [RL140; MeOCH 2, c-Pr], [RL141 ; MeOCH 2, Bu], [ RL142; MeOCH 2, t-Bu], [RL143; MeOCH 2, c-PrCH 2], [RL144; MeOCH 2, Ph], [RL145; MeOCH 2, Bn], [RL146 MeOCH 2 , CF 3 ], [RL 147; MeOCH 2 , CF 3 CH 2 ], [RL 148; MeOCH 2 , CF 3 CF 2 ], [RL 149; MeOCH 2 , CF 2 H], [RL 150; MeOCH 2 , CF 2 HCH 2 ], [RL 151; EtOCH 2 , Me], [RL 152; EtOCH 2 , Et], [RL153; EtOCH 2, Pr], [RL154; EtOCH 2, i-Pr], [RL155; EtOCH 2, c-Pr], [RL156; EtOCH 2, Bu], [RL157; EtOCH 2, t-Bu], [RL 158; EtOCH 2 , c-PrCH 2 ], [RL 159; EtOCH 2 , Ph], [RL 160; EtOCH 2 , Bn], [RL 161; EtOCH 2 , CF 3 ], [RL 162; EtOCH 2 , CF 3 CH 2 ], [RL 163; EtOCH 2 , CF 3 CF 2 ], [RL 164; EtOCH 2 , CF 2 H], [RL 165; EtOCH 2 , CF 2 HCH 2 ], [RL 166; CH 2 CH 2 CH 2 ], [RL 167; CH 2 CH 2 CH 2 CH 2 ], [RL 168; t-Bu, Me], [RL 169; t-Bu, Et], [RL 170; t-Bu, Pr], [RL 171; t -Bu, i-Pr], [RL 172; t-Bu, c-Pr], [RL 173; t-Bu, t-Bu], [RL 174; t-Bu, Bu], [RL 175; t-Bu, t -Bu], [RL 176; t-Bu, c-PrCH 2 ], [RL 177; t-Bu, Ph], [RL 178; t-Bu, Bn], [RL 179; t-Bu, CF 3 ], [RL 180] t-Bu, CF 3 CH 2 ], [RL 181; t-Bu, CF 3 CF 2 ], [RL 182; t-Bu, CF 2 H], [RL 183; t-Bu, CF 2 HCH 2 ], [RL 182; RL 184; i-Bu, Me], [RL 185; i-Bu, Et], [RL 186; i-Bu, Pr], [RL 187; i-Bu, i-Pr], [RL 188; i-Bu, c- Pr], [RL 189; i-Bu, t-Bu], [RL 190; i-Bu, Bu], [RL 191; i-Bu, t-Bu], [RL 192; i-Bu, c-PrCH 2 ], [RL 193; i-Bu, Ph], [RL 194; i-Bu, Bn], [RL 195; i-Bu, CF 3 ], [RL 196; i-Bu, CF 3 CH 2 ], [RL 197; i-Bu , CF 3 CF 2 ], [RL 198; i-Bu, CF 2 H], [RL 199; i-Bu, CF 2 HCH 2 ], [RL 200; HCCCH 2 , Me], [RL 201; HCC CH 2, Et], [RL202 ; HCCCH 2, Pr], [RL203; HCCCH 2, i-Pr], [RL204; HCCCH 2, c-Pr], [RL205; HCCCH 2, t-Bu], [RL206 ; HCCCH 2, Bu], [ RL207; HCCCH 2, t-Bu], [RL208; HCCCH 2, c-PrCH 2], [RL209; HCCCH 2, Ph], [RL210; HCCCH 2, Bn], [RL211 HCCCH 2 , CF 3 ], [RL 212; HCCCH 2 , CF 3 CH 2 ], [RL 213; HCCCH 2 , CF 3 CF 2 ], [RL 214; HCCCH 2 , CF 2 H], [RL 215; HCCCH 2 , CF 2 HCH 2], [RL216; MeCCCH 2, Me], [RL217; MeCCCH 2, Et], [RL218; MeCCCH 2, Pr], [RL219; MeCCCH 2, i-Pr], [RL220; MeCCCH 2, c -Pr], [RL221; MeCCCH 2 , t-Bu], [RL222; MeCCCH 2, Bu], [RL223; MeCCCH 2, t-Bu], [RL224; MeCCCH 2, c-PrCH 2], [RL225; MeCCCH 2, Ph], [RL226 ; MeCCCH 2, Bn], [RL227; MeCCCH 2, CF 3], [RL228; MeCCCH 2, CF 3 CH 2], [RL229; MeCCCH 2, CF 3 CF 2], [ RL230; MeCCCH 2, CF 2 H ], [RL231; MeCCCH 2, CF 2 HCH 2], [RL232; MeSCH 2, Me], [RL233; MeSCH 2, Et], [RL234; MeSCH 2, Pr], [ RL235; MeSCH 2, i-Pr ], [RL236; MeSCH 2, c-Pr], [RL237; MeSCH 2, t-Bu], [RL238; MeSCH 2, Bu], [RL239; MeSCH 2, t-Bu ], [RL240; MeSCH 2, c-PrCH 2], [RL241; MeSCH 2, Ph], [RL242; MeSCH 2, Bn], [RL243; MeSCH 2, CF 3], [RL244; MeSCH 2, CF 3 C H 2 ], [RL245; MeSCH 2 , CF 3 CF 2 ], [RL 246; MeSCH 2 , CF 2 H], [RL 247; MeSCH 2 , CF 2 HCH 2 ], [RL 248; EtSCH 2 , Me], [RL 249 EtSCH 2 , Et], [RL 250; EtSCH 2 , Pr],

[RL251;EtSCH2,i-Pr],[RL252;EtSCH2,c-Pr],[RL253;EtSCH2,t-Bu],[RL254;EtSCH2,Bu],[RL255;EtSCH2,t-Bu],[RL256;EtSCH2,c-PrCH2],[RL257;EtSCH2,Ph],[RL258;EtSCH2,Bn],[RL259;EtSCH2,CF3],[RL260;EtSCH2,CF3CH2],[RL261;EtSCH2,CF3CF2],[RL262;EtSCH2,CF2H],[RL263;EtSCH2,CF2HCH2],[RL264;2-Me-Ph,Me],[RL265;2-Me-Ph,Et],[RL266;2-Me-Ph,Pr],[RL267;2-Me-Ph,i-Pr],[RL268;2-Me-Ph,c-Pr],[RL269;2-Me-Ph,t-Bu],[RL270;2-Me-Ph,Bu],[RL271;2-Me-Ph,t-Bu],[RL272;2-Me-Ph,c-PrCH2],[RL273;2-Me-Ph,Ph],[RL274;2-Me-Ph,Bn],[RL275;2-Me-Ph,CF3],[RL276;2-Me-Ph,CF3CH2],[RL277;2-Me-Ph,CF3CF2],[RL278;2-Me-Ph,CF2H],[RL279;2-Me-Ph,CF2HCH2],[RL280;3-Me-Ph,Me],[RL281;3-Me-Ph,Et],[RL282;3-Me-Ph,Pr],[RL283;3-Me-Ph,i-Pr],[RL284;3-Me-Ph,c-Pr],[RL285;3-Me-Ph,t-Bu],[RL286;3-Me-Ph,Bu],[RL287;3-Me-Ph,t-Bu],[RL288;3-Me-Ph,c-PrCH2],[RL289;3-Me-Ph,Ph],[RL290;3-Me-Ph,Bn],[RL291;3-Me-Ph,CF3],[RL292;3-Me-Ph,CF3CH2],[RL293;3-Me-Ph,CF3CF2],[RL294;3-Me-Ph,CF2H],[RL295;3-Me-Ph,CF2HCH2],[RL296;4-Me-Ph,Me],[RL297;4-Me-Ph,Et],[RL298;4-Me-Ph,Pr],[RL299;4-Me-Ph,i-Pr],[RL300;4-Me-Ph,c-Pr],[RL301;4-Me-Ph,t-Bu],[RL302;4-Me-Ph,Bu],[RL303;4-Me-Ph,t-Bu],[RL304;4-Me-Ph,c-PrCH2],[RL305;4-Me-Ph,Ph],[RL306;4-Me-Ph,Bn],[RL307;4-Me-Ph,CF3],[RL308;4-Me-Ph,CF3CH2],[RL309;4-Me-Ph,CF3CF2],[RL310;4-Me-Ph,CF2H],[RL311;4-Me-Ph,CF2HCH2],[RL312;2-F-Ph,Me],[RL313;2-F-Ph,Et],[RL314;2-F-Ph,Pr],[RL315;2-F-Ph,i-Pr],[RL316;2-F-Ph,c-Pr],[RL317;2-F-Ph,t-Bu],[RL318;2-F-Ph,Bu],[RL319;2-F-Ph,t-Bu],[RL320;2-F-Ph,c-PrCH2],[RL321;2-F-Ph,Ph],[RL322;2-F-Ph,Bn],[RL323;2-F-Ph,CF3],[RL324;2-F-Ph,CF3CH2],[RL325;2-F-Ph,CF3CF2],[RL326;2-F-Ph,CF2H],[RL327;2-F-Ph,CF2HCH2],[RL328;3-F-Ph,Me],[RL329;3-F-Ph,Et],[RL330;3-F-Ph,Pr],[RL331;3-F-Ph,i-Pr],[RL332;3-F-Ph,c-Pr],[RL333;3-F-Ph,t-Bu],[RL334;3-F-Ph,Bu],[RL335;3-F-Ph,t-Bu],[RL336;3-F-Ph,c-PrCH2],[RL337;3-F-Ph,Ph],[RL338;3-F-Ph,Bn],[RL339;3-F-Ph,CF3],[RL340;3-F-Ph,CF3CH2],[RL341;3-F-Ph,CF3CF2],[RL342;3-F-Ph,CF2H],[RL343;3-F-Ph,CF2HCH2],[RL344;4-F-Ph,Me],[RL345;4-F-Ph,Et],[RL346;4-F-Ph,Pr],[RL347;4-F-Ph,i-Pr],[RL348;4-F-Ph,c-Pr],[RL349;4-F-Ph,t-Bu],[RL350;4-F-Ph,Bu],[RL351;4-F-Ph,t-Bu],[RL352;4-F-Ph,c-PrCH2],[RL353;4-F-Ph,Ph],[RL354;4-F-Ph,Bn],[RL355;4-F-Ph,CF3],[RL356;4-F-Ph,CF3CH2],[RL357;4-F-Ph,CF3CF2],[RL358;4-F-Ph,CF2H],[RL359;4-F-Ph,CF2HCH2],[RL360;2-MeO-Ph,Me],[RL361;2-MeO-Ph,Et],[RL362;2-MeO-Ph,Pr],[RL363;2-MeO-Ph,i-Pr],[RL364;2-MeO-Ph,c-Pr],[RL365;2-MeO-Ph,t-Bu],[RL366;2-MeO-Ph,Bu],[RL367;2-MeO-Ph,t-Bu],[RL368;2-MeO-Ph,c-PrCH2],[RL369;2-MeO-Ph,Ph],[RL370;2-MeO-Ph,Bn],[RL371;2-MeO-Ph,CF3],[RL372;2-MeO-Ph,CF3CH2],[RL373;2-MeO-Ph,CF3CF2],[RL374;2-MeO-Ph,CF2H],[RL375;2-MeO-Ph,CF2HCH2],[RL376;3-MeO-Ph,Me],[RL377;3-MeO-Ph,Et],[RL378;3-MeO-Ph,Pr],[RL379;3-MeO-Ph,i-Pr],[RL380;3-MeO-Ph,c-Pr],[RL381;3-MeO-Ph,t-Bu],[RL382;3-MeO-Ph,Bu],[RL383;3-MeO-Ph,t-Bu],[RL384;3-MeO-Ph,c-PrCH2],[RL385;3-MeO-Ph,Ph],[RL386;3-MeO-Ph,Bn],[RL387;3-MeO-Ph,CF3],[RL388;3-MeO-Ph,CF3CH2],[RL389;3-MeO-Ph,CF3CF2],[RL390;3-MeO-Ph,CF2H],[RL391;3-MeO-Ph,CF2HCH2],[RL392;4-MeO-Ph,Me],[RL393;4-MeO-Ph,Et],[RL394;4-MeO-Ph,Pr],[RL395;4-MeO-Ph,i-Pr],[RL396;4-MeO-Ph,c-Pr],[RL397;4-MeO-Ph,t-Bu],[RL398;4-MeO-Ph,Bu],[RL399;4-MeO-Ph,t-Bu],[RL400;4-MeO-Ph,c-PrCH2],[RL401;4-MeO-Ph,Ph],[RL402;4-MeO-Ph,Bn],[RL403;4-MeO-Ph,CF3],[RL404;4-MeO-Ph,CF3CH2],[RL405;4-MeO-Ph,CF3CF2],[RL406;4-MeO-Ph,CF2H],[RL407;4-MeO-Ph,CF2HCH2]
[RL 251; EtSCH 2 , i-Pr], [RL 252; EtSCH 2 , c-Pr], [RL 253; EtSCH 2 , t-Bu], [RL 254; EtSCH 2 , Bu], [RL 255; EtSCH 2 , t- Bu], [RL256; EtSCH 2 , c-PrCH 2], [RL257; EtSCH 2, Ph], [RL258; EtSCH 2, Bn], [RL259; EtSCH 2, CF 3], [RL260; EtSCH 2, CF 3 CH 2 ], [RL 261; EtSCH 2 , CF 3 CF 2 ], [RL 262; EtSCH 2 , CF 2 H], [RL 263; EtSCH 2 , CF 2 HCH 2 ], [RL 264; 2-Me-Ph, Me ], [RL 265; 2-Me-Ph, Et], [RL 266; 2-Me-Ph, Pr], [RL 267; 2-Me-Ph, i-Pr], [RL 268; 2-Me-Ph, c] -Pr], [RL 269; 2-Me-Ph, t-Bu], [RL 270; 2-Me-Ph, Bu], [RL 271; 2-Me-Ph, t-Bu], [RL 272; -Ph, c-PrCH 2], [RL273; 2-Me-Ph, Ph], [RL274; 2-Me-Ph, Bn], [RL275; 2-Me-Ph, CF 3], [RL276; 2 -Me-Ph, CF 3 CH 2 ], [RL277; 2-Me-Ph, CF 3 CF 2], [RL278; 2-Me-Ph, CF 2 H], [RL279; 2-Me-Ph, CF 2 HCH 2 ], [RL 280; 3-Me-Ph, Me], [RL 281; 3-Me-Ph, Et], [RL 282, 3-Me-Ph, Pr], [RL 283; 3-Me-Ph, i-Pr], [RL 284; 3-Me-Ph, c-Pr], [RL 285; 3-Me-Ph, t-Bu], [RL 286; 3-Me-Ph, Bu], [RL 287; Me-Ph, t-Bu], [RL 288; 3-Me-Ph, c-PrCH 2 ], [RL 289; 3-Me-Ph, Ph], [RL 290; 3-Me-Ph, Bn], [RL 291 ; 3-Me-Ph, CF 3], [RL292; 3-Me-Ph, CF 3 CH 2], [RL293; 3-Me-Ph, CF 3 CF 2], [RL294; 3-Me-Ph, CF 2 H], [RL 295; 3-Me-Ph, CF 2 HCH 2], [RL296; 4 -Me-Ph, Me], [RL297; 4-Me-Ph, Et], [RL298; 4-Me-Ph, Pr], [RL299; 4-Me-Ph, i -Pr], [RL 300; 4-Me-Ph, c-Pr], [RL 301; 4-Me-Ph, t-Bu], [RL 302; 4-Me-Ph, Bu], [RL 303; -Ph, t-Bu], [RL 304; 4-Me-Ph, c-PrCH 2 ], [RL 305; 4-Me-Ph, Ph], [RL 306; 4-Me-Ph, Bn], [RL 307; 4-Me-Ph, CF 3 ], [RL308; 4-Me-Ph, CF 3 CH 2], [RL309; 4-Me-Ph, CF 3 CF 2], [RL310; 4-Me-Ph, CF 2 H], [RL 311; 4-Me-Ph, CF 2 HCH 2 ], [RL 312; 2-F-Ph, Me], [RL 313; 2-F-Ph, Et], [RL 314; 2-F- Ph, Pr], [RL 315; 2-F-Ph, i-Pr], [RL 316; 2-F-Ph, c-Pr], [RL 317; 2-F-Ph, t-Bu], [RL 318; 2-F-Ph, Bu], [RL 319; 2-F-Ph, t-Bu], [RL 320; 2-F-Ph, c-PrCH 2 ], [RL 321; 2-F-Ph, Ph], [RL 322; 2-F-Ph, Bn], [RL 323; 2-F-Ph, CF 3 ], [RL 324; 2-F-Ph, CF 3 CH 2 ], [RL 325; 2-F-Ph, CF] 3 CF 2 ], [RL 326; 2-F-Ph, CF 2 H], [RL 327; 2-F-Ph, CF 2 HCH 2 ], [RL 328; 3-F-Ph, Me], [RL 329] -F-Ph, Et], [RL 330; 3-F-Ph, Pr], [RL 331; 3-F-Ph, i-Pr], [RL 332; 3-F-Ph, c-Pr], [RL 333 3-F-Ph, t-Bu], [RL 334; 3-F-Ph, Bu], [RL 335; 3-F-Ph, t-Bu], [RL 336; 3-F-Ph, c-PrCH 2 ], [RL 337; 3-F-Ph, Ph], [RL 338; 3-F-Ph, Bn], [RL 339; 3-F-Ph, CF 3 ], [RL 340; 3-F-Ph, CF] 3 CH 2 ], [RL 341; 3-F-Ph, CF 3 CF 2 ], [RL 342; 3-F-Ph, CF 2 H], [RL343; 3- F-Ph, CF 2 HCH 2], [RL344; 4-F-Ph, Me], [RL345; 4-F-Ph, Et], [RL346; 4-F-Ph , Pr], [RL 347; 4-F-Ph, i-Pr], [RL 348; 4-F-Ph, c-Pr], [RL 349; 4-F-Ph, t-Bu], [RL 350; -F-Ph, Bu], [RL 351; 4-F-Ph, t-Bu], [RL 352; 4-F-Ph, c-PrCH 2 ], [RL 353; 4-F-Ph, Ph], [[R 353; RL354; 4-F-Ph, Bn], [RL355; 4-F-Ph, CF 3], [RL356; 4-F-Ph, CF 3 CH 2], [RL357; 4-F-Ph, CF 3 CF 2 ], [RL 358; 4-F-Ph, CF 2 H], [RL 359; 4-F-Ph, CF 2 HCH 2 ], [RL 360; 2-MeO-Ph, Me], [RL 361; MeO-Ph, Et], [RL 362; 2-MeO-Ph, Pr], [RL 363; 2-MeO-Ph, i-Pr], [RL 364; 2-MeO-Ph, c-Pr], [RL 365; 2-MeO-Ph, t-Bu], [RL 366; 2-MeO-Ph, Bu], [RL 367; 2-MeO-Ph, t-Bu], [RL 368; 2-MeO-Ph, c-PrCH 2 ], [RL 369; 2-MeO-Ph, Ph], [RL 370; 2-MeO-Ph, Bn], [RL 371; 2-MeO-Ph, CF 3 ], [RL 372; 2-MeO-Ph, CF 3] CH 2], [RL373; 2 -MeO-Ph, CF 3 CF 2], [RL374; 2-MeO-Ph, CF 2 H], [RL375; 2-MeO-Ph, CF 2 HCH 2], [RL376 3-MeO-Ph, Me], [RL 377; 3-MeO-Ph, Et], [RL 378; 3-MeO-Ph, Pr], [RL 379; 3-MeO-Ph, i-Pr], [RL 380; 3-MeO-Ph, c-Pr], [RL 381; 3-MeO-Ph, t-Bu], [RL 382; 3-MeO-Ph, Bu], [RL 383; 3-MeO-Ph, t-Bu ], [RL 384; 3-MeO-Ph, c-PrCH 2 ], [RL 385; 3-MeO-Ph, Ph], [RL 386; 3-MeO-Ph, Bn], [RL 387; 3-MeO-Ph, CF 3 ], [RL 388; 3-M eO-Ph, CF 3 CH 2 ], [RL389; 3-MeO-Ph, CF 3 CF 2], [RL390; 3-MeO-Ph, CF 2 H], [RL391; 3-MeO-Ph, CF 2 HCH 2 ], [RL 392; 4-MeO-Ph, Me], [RL 393; 4-MeO-Ph, Et], [RL 394; 4-MeO-Ph, Pr], [RL 395; 4-MeO-Ph, i -Pr], [RL 396; 4-MeO-Ph, c-Pr], [RL 397; 4-MeO-Ph, t-Bu], [RL 398; 4-MeO-Ph, Bu], [RL 399; 4-MeO -Ph, t-Bu], [RL 400; 4-MeO-Ph, c-PrCH 2 ], [RL 401; 4-MeO-Ph, Ph], [RL 402; 4-MeO-Ph, Bn], [RL 403; 4-MeO-Ph, CF 3 ], [RL404; 4-MeO-Ph, CF 3 CH 2], [RL405; 4-MeO-Ph, CF 3 CF 2], [RL406; 4-MeO-Ph, CF 2 H], [RL 407; 4-MeO-Ph, CF 2 HCH 2 ]

式(XIV)

Figure 2019089711
〔式中、R32及びR33は各々独立して、水素原子、群E及び群Fからなる群より選ばれる1以上の置換基を有していてもよいC1−C6アルキル基、1以上のハロゲン原子を有していてもよいC3−C6アルキニル基、1以上のハロゲン原子を有していてもよいC1−C6アルコキシ基、群Dより選ばれる1以上の置換基を有していてもよいC3−C6シクロアルキル基もしくは群Dより選ばれる1以上の置換基を有していてもよいフェニル基を表すか、又はR32とR33とは、互いに結合して3−6員ヘテロ環(該3−6員ヘテロ環は群Dより選ばれる1以上の置換基を有していてもよい)を形成していてもよい。〕
で表される化合物において、R32及びR33の組合わせが下記に示される置換基番号RM1〜RM130のいずれかに記載の組合わせである化合物(以下、置換基番号RM1〜RM130の化合物を本発明化合物RM1〜RM130と表し、本発明化合物RM1〜RM130をまとめて本発明化合物RMと表す)は、上記の製造法に記載の方法に準じて得ることができる。
なお、置換基番号RM1〜RM130とは、式(XIV)で表される化合物における、R32及びR33の組合せを表すものであり、以下、[置換基番号;R32,R33]と記す。ただし、置換基番号RM127〜RM129においては、R32とR33とが、互いに結合してヘテロ環を形成することを表す。
例えば、置換基番号RM4とは、R32が水素原子であり、R12がイソプロピル基である組合せを表す。 Formula (XIV)
Figure 2019089711
[Wherein, R 32 and R 33 each independently represent a hydrogen atom, a C 1 -C 6 alkyl group optionally having one or more substituents selected from the group consisting of Group E and Group F, one or more A C3-C6 alkynyl group which may have a halogen atom, a C1-C6 alkoxy group which may have one or more halogen atoms, and one or more substituents selected from Group D A C3-C6 cycloalkyl group or a phenyl group which may have one or more substituents selected from group D, or R 32 and R 33 are bonded to each other to form a 3- to 6-membered heterocyclic ring ( The 3- to 6-membered heterocyclic ring may form one or more substituents selected from Group D). ]
Wherein the combination of R 32 and R 33 is a combination according to any one of the substituent numbers RM 1 to RM 130 shown below (hereinafter referred to as a compound of the substituent numbers RM 1 to RM 130 Invention compounds RM1 to RM130, and the compounds of the present invention RM1 to RM130 are collectively referred to as the compound of the invention RM) can be obtained according to the method described in the above-mentioned production method.
Substituent numbers RM1 to RM130 each represent a combination of R 32 and R 33 in the compound represented by formula (XIV), and hereinafter referred to as [substituent number; R 32 , R 33 ] . However, in Substituent Nos. RM127 to RM129, R 32 and R 33 represent that they combine with each other to form a heterocycle.
For example, the substituent number RM4 represents a combination in which R 32 is a hydrogen atom and R 12 is an isopropyl group.

ここで、R32とR33とが互いに結合して形成する3−6員ヘテロ環とは、下記(ZB1〜ZB4及びZB7〜ZB21)に示すいずれかの構造を表す(●は結合位置を表す)。

Figure 2019089711
Here, the 3- to 6-membered heterocyclic ring formed by bonding R 32 and R 33 to each other represents any structure shown in the following (ZB1 to ZB4 and ZB7 to ZB21) (● represents a bonding position) ).

Figure 2019089711

例えば、本発明化合物RM4とは、式(XIV)で表される化合物において置換基番号がRM4である化合物を意味し、式(XIV)で表される化合物において、R32が水素原子であり、R33がイソプロピル基である下記の化合物を表す。

Figure 2019089711
For example, the compound RM4 of the present invention means a compound represented by the formula (XIV) in which the substituent number is RM4, and in the compound represented by the formula (XIV), R 32 is a hydrogen atom, It represents the following compound wherein R 33 is an isopropyl group.
Figure 2019089711

[置換基番号;R32,R33]:[RM1;H,Me],[RM2;H,Et],[RM3;H,Pr],[RM4;H,i-Pr],[RM5;H,c-Pr],[RM6;H,Bu],[RM7;H,t-Bu],[RM8;H,c-PrCH2],[RM9;H,Ph],[RM10;H,Bn],[RM11;H,CF3CH2],[RM12;H,CF2HCH2],[RM13;H,CHCCH2],[RM14;H,MeCCCH2],[RM15;Me,Me],[RM16;Me,Et],[RM17;Me,Pr],[RM18;Me,i-Pr],[RM19;Me,c-Pr],[RM20;Me,Bu],[RM21;Me,t-Bu],[RM22;Me,c-PrCH2],[RM23;Me,Ph],[RM24;Me,Bn],[RM25;Me,CF3CH2],[RM26;Me,CF2HCH2],[RM27;Me,CHCCH2],[RM28;Me,MeCCCH2],[RM29;Et,Et],[RM30;Et,Pr],[RM31;Et,i-Pr],[RM32;Et,c-Pr],[RM33;Et,Bu],[RM34;Et,t-Bu],[RM35;Et,c-PrCH2],[RM36;Et,Ph],[RM37;Et,Bn],[RM38;Et,CF3CH2],[RM39;Et,CF2HCH2],[RM40;Et,CHCCH2],[RM41;Et,MeCCCH2],[RM42;Pr,Pr],[RM43;Pr,i-Pr],[RM44;Prc-Pr],[RM45;Pr,Bu],[RM46;Pr,t-Bu],[RM47;Pr,c-PrCH2],[RM48;Pr,Ph],[RM49;Pr,Bn],[RM50;Pr,CF3CH2],[RM51;Pr,CF2HCH2],[RM52;Pr,CHCCH2],[RM53;Pr,MeCCCH2],[RM54;i-Pr,i-Pr],[RM55;i-Pr,c-Pr],[RM56;i-Pr,Bu],[RM57;i-Pr,t-Bu],[RM58;i-Pr,c-PrCH2],[RM59;i-Pr,Ph],[RM60;i-Pr,Bn],[RM61;i-Pr,CF3CH2],[RM62;i-Pr,CF2HCH2],[RM63;i-Pr,CHCCH2],[RM64;i-Pr,MeCCCH2],[RM65;c-Pr,c-Pr],[RM66;c-Pr,Bu],[RM67;c-Pr,t-Bu],[RM68;c-Pr,c-PrCH2],[RM69;c-Pr,Ph],[RM70;c-Pr,Bn],[RM71;c-Pr,CF3CH2],[RM72;c-Pr,CF2HCH2],[RM73;c-Pr,CHCCH2],[RM74;c-Pr,MeCCCH2],[RM75;c-PrCH2,Bu],[RM76;c-PrCH2,t-Bu],[RM77;c-PrCH2,c-PrCH2],[RM78;c-PrCH2,Ph],[RM79;c-PrCH2,Bn],[RM80;c-PrCH2,CF3CH2],[RM81;c-PrCH2,CF2HCH2],[RM82;c-PrCH2,CHCCH2],[RM83;c-PrCH2,MeCCCH2],[RM84;CF3CH2,Bu],[RM85;CF3CH2,t-Bu],[RM86;CF3CH2,Ph],[RM87;CF3CH2,Bn],[RM88;CF3CH2,CF3CH2],[RM89;CF3CH2,CF2HCH2],[RM90;CF3CH2,CHCCH2],[RM91;CF3CH2,MeCCCH2],[RM92;CF2HCH2,Bu],[RM93;CF2HCH2,t-Bu],[RM94;CF2HCH2,Ph],[RM95;CF2HCH2,Bn],[RM96;CF2HCH2,CF2HCH2],[RM97;CF2HCH2,CHCCH2],[RM98;CF2HCH2,MeCCCH2],[RM99;MeOCH2,Me],[RM100;MeOCH2,Et],[RM101;MeOCH2,Pr],[RM102;MeOCH2,i-Pr],[RM103;MeOCH2,c-Pr],[RM104;MeOCH2,Bu],[RM105;MeOCH2,t-Bu],[RM106;MeOCH2,c-PrCH2],[RM107;MeOCH2,Ph],[RM108;MeOCH2,Bn],[RM109;MeOCH2,CF3CH2],[RM110;MeOCH2,CF2HCH2],[RM111;MeOCH2,CHCCH2],[RM112;MeOCH2,MeCCCH2],[RM113;EtOCH2,Me],[RM114;EtOCH2,Et],[RM115;EtOCH2,Pr],[RM116;EtOCH2,i-Pr],[RM117;EtOCH2,c-Pr],[RM118;EtOCH2,Bu],[RM119;EtOCH2,t-Bu],[RM120;EtOCH2,c-PrCH2],[RM121;EtOCH2,Ph],[RM122;EtOCH2,Bn],[RM123;EtOCH2,CF3CH2],[RM124;EtOCH2,CF2HCH2],[RM125;EtOCH2,CHCCH2],[RM126;EtOCH2,MeCCCH2],[RM127;CH2(CH2)2CH2],[RM128;CH2(CH2)3CH2],[RM129;CH2CH2OCH2CH2],[RM130;H,H] [Substituent number; R 32 , R 33 ]: [RM 1; H, Me], [RM 2; H, Et], [RM 3; H, Pr], [RM 4; H, i-Pr], [RM 5; , c-Pr], [RM 6; H, Bu], [RM 7; H, t-Bu], [RM 8; H, c-PrCH 2 ], [RM 9; H, Ph], [RM 10; H, Bn] , [RM11; H, CF 3 CH 2], [RM12; H, CF 2 HCH 2], [RM13; H, CHCCH 2], [RM14; H, MeCCCH 2], [RM15; Me, Me], [ RM16; Me, Et], [RM17; Me, Pr], [RM18; Me, i-Pr], [RM19; Me, c-Pr], [RM20; Me, Bu], [RM21; Me, t- Bu], [RM22; Me, c-PrCH 2], [RM23; Me, Ph], [RM24; Me, Bn], [RM25; Me, CF 3 CH 2], [RM26; Me, CF 2 HCH 2 ], [RM 27; Me, CHCCH 2 ], [RM 28; Me, MeCCCH 2 ], [RM 29; Et, Et], [RM 30; Et, Pr], [RM 31; Et, i-Pr], [RM 32; , c-Pr], [RM 33; Et, Bu], [RM 34; Et, t-Bu], [RM 35; Et, c-PrCH 2 ], [RM 36; Et, Ph], [RM 37; Et, Bn] , [RM 38; Et, CF 3 CH 2 ], [RM 39; Et, CF 2 HCH 2 ], [RM 40; Et, CHCCH 2 ], [RM 41; Et, MeCCCH 2 ], [RM 42; Pr, Pr], [RM 38; RM 43; Pr, i-Pr], [RM 44; Prc-Pr], [RM 45; Pr, Bu], [RM 46; Pr, t-Bu], [RM 47; Pr, c-PrCH 2 ], [RM 48; , Ph], [RM 49; Pr, Bn], [RM 50; Pr, CF 3 CH 2 ], [RM 51; Pr, CF 2 HCH 2 ], [RM 52; Pr, CHCCH 2 ], [RM 53; Pr, MeCCCH 2 ], [RM 54; i-Pr, i-Pr], [RM 55; i-Pr, c-Pr], [RM 56; i-Pr, Bu], [RM 57; i-Pr, t-Bu], [RM 58 i-Pr, c-PrCH 2 ], [RM 59; i-Pr, Ph], [RM 60; i-Pr, Bn], [RM 61; i-Pr, CF 3 CH 2], [RM62; i -Pr, CF 2 HCH 2], [RM63; i-Pr, CHCCH 2], [RM64; i-Pr, MeCCCH 2], [RM65; c-Pr, c-Pr] , [RM 66; c-Pr, Bu], [RM 67; c-Pr, t-Bu], [RM 68; c-Pr, c-PrCH 2 ], [RM 69; c-Pr, Ph], [RM 70; -Pr, Bn], [RM 71; c-Pr, CF 3 CH 2 ], [RM 72; c-Pr, CF 2 HCH 2 ], [RM 73; c-Pr, CHCCH 2 ], [RM 74; c-Pr, MeCCCH 2], [RM75; c -PrCH 2, Bu], [RM76; c-PrCH 2, t-Bu], [RM77; c-PrCH 2, c-PrCH 2], [RM78; c-PrCH 2, Ph], [RM79; c- PrCH 2, Bn], [RM80; c-PrCH 2, CF 3 CH 2], [RM81; c-PrCH 2, CF 2 HCH 2], [RM82; c-PrCH 2, CHCCH 2], [RM83; c -PrCH 2, MeCCCH 2], [RM84; CF 3 CH 2, Bu], [RM85; CF 3 CH 2, t-Bu], [RM86; CF 3 CH 2, Ph] , [RM 87; CF 3 CH 2 , Bn], [RM 88; CF 3 CH 2 , CF 3 CH 2 ], [RM 89; CF 3 CH 2 , CF 2 HCH 2 ], [RM 90; CF 3 CH 2 , CHCCH 2 ], [RM91; CF 3 CH 2, MeCCCH 2], [RM92; CF 2 HCH 2, Bu], [RM93; CF 2 HCH 2, t-Bu], [RM94; CF 2 HCH 2, Ph], [ RM 95; CF 2 HCH 2 , Bn], [RM 96; CF 2 HCH 2 , CF 2 HCH 2 ], [RM 97; CF 2 HCH 2 , CHCCH 2 ], [RM 98; CF 2 HCH 2 , MeCCCH 2 ], [RM 99 ; MeOCH 2, Me], [ RM100; MeOCH 2, Et], [RM101; MeOCH 2, Pr], [RM102; MeOCH 2, i-Pr], [RM103; MeOCH 2, c-Pr], [RM104; MeOCH 2 , Bu], [RM 105; MeOCH 2 , t-Bu], [RM106 ; MeOCH 2, c-PrCH 2], [RM107; MeOCH 2, Ph], [RM108; MeOCH 2, Bn], [RM109; MeOCH 2, CF 3 CH 2], [RM110 ; MeOCH 2, CF 2 HCH 2 ], [RM111; MeOCH 2, CHCCH 2], [RM112; MeOCH 2, MeCCCH 2], [RM113; EtOCH 2, Me], [RM114; EtOCH 2, Et], [RM115 EtOCH 2 , Pr], [RM 116; EtOCH 2 , i-Pr], [RM 117; EtOCH 2 , c-Pr], [RM 118; EtOCH 2 , Bu], [RM 119; EtOCH 2 , t-Bu], [RM RM120; EtOCH 2, c-PrCH 2], [RM121; EtOCH 2, Ph], [RM122; EtOCH 2, Bn], [RM123; EtOCH 2, CF 3 CH 2], [RM124; EtOCH 2, CF 2 HCH 2], [RM125; EtOCH 2 , CHCCH 2], [RM126; EtOCH 2, MeCCCH 2], [RM127; CH 2 (CH 2) 2 CH 2], [RM128; CH 2 (CH 2) 3 CH 2] , [RM129; CH 2 CH 2 OCH 2 CH 2 ], [RM 130; H, H]

式(XV)

Figure 2019089711
〔式中、R32及びR33は上記と同じ意味を表す。〕
で表される化合物において、R32及びR33の組合わせが下記に示される置換基番号RN1〜RN130のいずれかに記載の組合わせである化合物(以下、置換基番号RN1〜RN130の化合物を本発明化合物RN1〜RN130と表し、本発明化合物RN1〜RN130をまとめて本発明化合物RNと表す)は、上記の製造法に記載の方法に準じて得ることができる。
なお、置換基番号RN1〜RN130とは、式(XV)で表される化合物における、R32及びR33の組合せを表すものであり、以下、[置換基番号;R32,R33]と記す。ただし、置換基番号RN127〜RN129においては、R32とR33とが、互いに結合してヘテロ環を形成することを表す。
例えば、置換基番号RN4とは、R32が水素原子であり、R33がイソプロピル基である組合せを表す。 Formula (XV)
Figure 2019089711
[Wherein, R 32 and R 33 represent the same meaning as described above. ]
Wherein the combination of R 32 and R 33 is a combination as set forth in any of Substituent Nos. RN 1 to RN 130 shown below (hereinafter referred to as “compound of Substituent Nos. RN 1 to RN 130” Inventive compounds RN1 to RN130, and the compounds of the present invention RN1 to RN130 are collectively referred to as the compound of the present invention RN) can be obtained according to the method described in the above-mentioned production method.
The substituent numbers RN1 to RN130 represent a combination of R 32 and R 33 in the compound represented by the formula (XV), and hereinafter, referred to as [substituent number: R 32 , R 33 ] . However, in Substituent Nos. RN127 to RN129, R 32 and R 33 represent that they combine with each other to form a heterocycle.
For example, the substituent number RN4 represents a combination in which R 32 is a hydrogen atom and R 33 is an isopropyl group.

例えば、本発明化合物RN4とは、式(XV)で表される化合物において置換基番号がRN4である化合物を意味し、式(XV)で表される化合物において、R32が水素原子であり、R33がイソプロピル基である下記の化合物を表す。

Figure 2019089711
For example, the compound RN4 of the present invention means a compound represented by the formula (XV) in which the substituent number is RN4, and in the compound represented by the formula (XV), R 32 is a hydrogen atom, It represents the following compound wherein R 33 is an isopropyl group.
Figure 2019089711

[置換基番号;R32,R33]:[RN1;H,Me],[RN2;H,Et],[RN3;H,Pr],[RN4;H,i-Pr],[RN5;H,c-Pr],[RN6;H,Bu],[RN7;H,t-Bu],[RN8;H,c-PrCH2],[RN9;H,Ph],[RN10;H,Bn],[RN11;H,CF3CH2],[RN12;H,CF2HCH2],[RN13;H,CHCCH2],[RN14;H,MeCCCH2],[RN15;Me,Me],[RN16;Me,Et],[RN17;Me,Pr],[RN18;Me,i-Pr],[RN19;Me,c-Pr],[RN20;Me,Bu],[RN21;Me,t-Bu],[RN22;Me,c-PrCH2],[RN23;Me,Ph],[RN24;Me,Bn],[RN25;Me,CF3CH2],[RN26;Me,CF2HCH2],[RN27;Me,CHCCH2],[RN28;Me,MeCCCH2],[RN29;Et,Et],[RN30;Et,Pr],[RN31;Et,i-Pr],[RN32;Et,c-Pr],[RN33;Et,Bu],[RN34;Et,t-Bu],[RN35;Et,c-PrCH2],[RN36;Et,Ph],[RN37;Et,Bn],[RN38;Et,CF3CH2],[RN39;Et,CF2HCH2],[RN40;Et,CHCCH2],[RN41;Et,MeCCCH2],[RN42;Pr,Pr],[RN43;Pr,i-Pr],[RN44;Prc-Pr],[RN45;Pr,Bu],[RN46;Pr,t-Bu],[RN47;Pr,c-PrCH2],[RN48;Pr,Ph],[RN49;Pr,Bn],[RN50;Pr,CF3CH2],[RN51;Pr,CF2HCH2],[RN52;Pr,CHCCH2],[RN53;Pr,MeCCCH2],[RN54;i-Pr,i-Pr],[RN55;i-Pr,c-Pr],[RN56;i-Pr,Bu],[RN57;i-Pr,t-Bu],[RN58;i-Pr,c-PrCH2],[RN59;i-Pr,Ph],[RN60;i-Pr,Bn],[RN61;i-Pr,CF3CH2],[RN62;i-Pr,CF2HCH2],[RN63;i-Pr,CHCCH2],[RN64;i-Pr,MeCCCH2],[RN65;c-Pr,c-Pr],[RN66;c-Pr,Bu],[RN67;c-Pr,t-Bu],[RN68;c-Pr,c-PrCH2],[RN69;c-Pr,Ph],[RN70;c-Pr,Bn],[RN71;c-Pr,CF3CH2],[RN72;c-Pr,CF2HCH2],[RN73;c-Pr,CHCCH2],[RN74;c-Pr,MeCCCH2],[RN75;c-PrCH2,Bu],[RN76;c-PrCH2,t-Bu],[RN77;c-PrCH2,c-PrCH2],[RN78;c-PrCH2,Ph],[RN79;c-PrCH2,Bn],[RN80;c-PrCH2,CF3CH2],[RN81;c-PrCH2,CF2HCH2],[RN82;c-PrCH2,CHCCH2],[RN83;c-PrCH2,MeCCCH2],[RN84;CF3CH2,Bu],[RN85;CF3CH2,t-Bu],[RN86;CF3CH2,Ph],[RN87;CF3CH2,Bn],[RN88;CF3CH2,CF3CH2],[RN89;CF3CH2,CF2HCH2],[RN90;CF3CH2,CHCCH2],[RN91;CF3CH2,MeCCCH2],[RN92;CF2HCH2,Bu],[RN93;CF2HCH2,t-Bu],[RN94;CF2HCH2,Ph],[RN95;CF2HCH2,Bn],[RN96;CF2HCH2,CF2HCH2],[RN97;CF2HCH2,CHCCH2],[RN98;CF2HCH2,MeCCCH2],[RN99;MeOCH2,Me],[RN100;MeOCH2,Et],[RN101;MeOCH2,Pr],[RN102;MeOCH2,i-Pr],[RN103;MeOCH2,c-Pr],[RN104;MeOCH2,Bu],[RN105;MeOCH2,t-Bu],[RN106;MeOCH2,c-PrCH2],[RN107;MeOCH2,Ph],[RN108;MeOCH2,Bn],[RN109;MeOCH2,CF3CH2],[RN110;MeOCH2,CF2HCH2],[RN111;MeOCH2,CHCCH2],[RN112;MeOCH2,MeCCCH2],[RN113;EtOCH2,Me],[RN114;EtOCH2,Et],[RN115;EtOCH2,Pr],[RN116;EtOCH2,i-Pr],[RN117;EtOCH2,c-Pr],[RN118;EtOCH2,Bu],[RN119;EtOCH2,t-Bu],[RN120;EtOCH2,c-PrCH2],[RN121;EtOCH2,Ph],[RN122;EtOCH2,Bn],[RN123;EtOCH2,CF3CH2],[RN124;EtOCH2,CF2HCH2],[RN125;EtOCH2,CHCCH2],[RN126;EtOCH2,MeCCCH2],[RN127;CH2(CH2)2CH2],[RN128;CH2(CH2)3CH2],[RN129;CH2CH2OCH2CH2],[RN130;H,H] [Substituent number; R 32 , R 33 ]: [RN1; H, Me], [RN2; H, Et], [RN3; H, Pr], [RN4; H, i-Pr], [RN5; H , c-Pr], [RN6 ; H, Bu], [RN7; H, t-Bu], [RN8; H, c-PrCH 2], [RN9; H, Ph], [RN10; H, Bn] , [RN11; H, CF 3 CH 2], [RN12; H, CF 2 HCH 2], [RN13; H, CHCCH 2], [RN14; H, MeCCCH 2], [RN15; Me, Me], [ RN16; Me, Et], [RN17; Me, Pr], [RN18; Me, i-Pr], [RN19; Me, c-Pr], [RN20; Me, Bu], [RN21; Me, t- Bu], [RN22; Me, c-PrCH 2], [RN23; Me, Ph], [RN24; Me, Bn], [RN25; Me, CF 3 CH 2], [RN26; Me, CF 2 HCH 2 ], [RN27; Me, CHCCH 2], [RN28; Me, MeCCCH 2], [RN29; Et, Et], [RN30; Et, Pr], [RN31; Et, i-Pr], [RN32; Et , c-Pr], [RN 33; Et, Bu], [RN 34; Et, t-Bu], [RN 35; Et, c-PrCH 2 ], [RN 36; Et, Ph], [RN 37; Et, Bn] , [RN38; Et, CF 3 CH 2], [RN39; Et, CF 2 HCH 2], [RN40; Et, CHCCH 2], [RN41; Et, MeCCCH 2], [RN42; Pr, Pr], [ RN43; Pr, i-Pr] , [RN44; Prc-Pr], [RN45; Pr, Bu], [RN46; Pr, t-Bu], [RN47; Pr, c-PrCH 2], [RN48; Pr , Ph], [RN 49; Pr, Bn], [RN 50; Pr, CF 3 CH 2 ], [RN 51; Pr, CF 2 HCH 2 ], [RN 52; Pr, CHCCH 2 ], [RN 53; Pr, MeCCCH 2 ], [RN54; i-Pr, i-Pr], [RN55; i-Pr, c-Pr], [RN56; i-Pr, Bu], [RN57; i-Pr, t-Bu], [RN58] i-Pr, c-PrCH 2 ], [RN 59; i-Pr, Ph], [RN 60; i-Pr, Bn], [RN 61; i-Pr, CF 3 CH 2], [RN62; i -Pr, CF 2 HCH 2], [RN63; i-Pr, CHCCH 2], [RN64; i-Pr, MeCCCH 2], [RN65; c-Pr, c-Pr] , [RN66; c-Pr, Bu], [RN67; c-Pr, t-Bu], [RN68; c-Pr, c-PrCH 2], [RN69; c-Pr, Ph], [RN70; c -Pr, Bn], [RN71; c-Pr, CF 3 CH 2], [RN72; c-Pr, CF 2 HCH 2], [RN73; c-Pr, CHCCH 2], [RN74; c-Pr, MeCCCH 2], [RN75; c -PrCH 2, Bu], [RN76; c-PrCH 2, t-Bu], [RN77; c-PrCH 2, c-PrCH 2], [RN78; c-PrCH 2, Ph], [RN 79; c-PrCH 2 , Bn], [RN 80; c-PrCH 2 , CF 3 CH 2 ], [RN 81; c-PrCH 2 , CF 2 HCH 2 ], [RN 82; c-PrCH 2 , CHCCH 2], [RN83; c -PrCH 2, MeCCCH 2], [RN84; CF 3 CH 2, Bu], [RN85; CF 3 CH 2, t-Bu], [RN86; CF 3 CH 2, Ph] , [RN 87; CF 3 CH 2 , Bn], [RN 88; CF 3 CH 2 , CF 3 CH 2 ], [RN 89; CF 3 CH 2 , CF 2 HCH 2 ], [RN 90; CF 3 CH 2 , CHCCH 2 ], [RN91; CF 3 CH 2, MeCCCH 2], [RN92; CF 2 HCH 2, Bu], [RN93; CF 2 HCH 2, t-Bu], [RN94; CF 2 HCH 2, Ph], [ RN95; CF 2 HCH 2, Bn ], [RN96; CF 2 HCH 2, CF 2 HCH 2], [RN97; CF 2 HCH 2, CHCCH 2], [RN98; CF 2 HCH 2, MeCCCH 2], [RN99 ; MeOCH 2, Me], [ RN100; MeOCH 2, Et], [RN101; MeOCH 2, Pr], [RN102; MeOCH 2, i-Pr], [RN103; MeOCH 2, c-Pr], [RN104; MeOCH 2 , Bu], [RN 105; MeOCH 2 , t-Bu], [RN106 ; MeOCH 2, c-PrCH 2], [RN107; MeOCH 2, Ph], [RN108; MeOCH 2, Bn], [RN109; MeOCH 2, CF 3 CH 2], [RN110 ; MeOCH 2, CF 2 HCH 2 ], [RN111; MeOCH 2, CHCCH 2], [RN112; MeOCH 2, MeCCCH 2], [RN113; EtOCH 2, Me], [RN114; EtOCH 2, Et], [RN115 ; EtOCH 2, Pr], [ RN116; EtOCH 2, i-Pr], [RN117; EtOCH 2, c-Pr], [RN118; EtOCH 2, Bu], [RN119; EtOCH 2, t-Bu], [ RN120; EtOCH 2, c-PrCH 2], [RN121; EtOCH 2, Ph], [RN122; EtOCH 2, Bn], [RN123; EtOCH 2, CF 3 CH 2], [RN124; EtOCH 2, CF 2 HCH 2 ], [RN 125; EtOCH 2 , CHCCH 2 ], [RN 126; EtOCH 2 , MeCCCH 2 ], [RN 127; CH 2 (CH 2 ) 2 CH 2 ], [RN 128; CH 2 (CH 2 ) 3 CH 2 ] , [RN 129; CH 2 CH 2 OCH 2 CH 2 ], [RN 130; H, H]

式(XVI)

Figure 2019089711
〔式中、R32及びR33は上記と同じ意味を表す。〕
で表される化合物において、R32及びR33の組合わせが下記に示される置換基番号RO1〜RO130のいずれかに記載の組合わせである化合物(以下、置換基番号RO1〜RO130の化合物を本発明化合物RO1〜RO130と表し、本発明化合物RO1〜RO130をまとめて本発明化合物ROと表す)は、上記の製造法に記載の方法に準じて得ることができる。
なお、置換基番号RO1〜RO130とは、式(XVI)で表される化合物における、R32及びR33の組合せを表すものであり、以下、[置換基番号;R32,R33]と記す。ただし、置換基番号RO127〜RO129においては、R32とR33とが、互いに結合してヘテロ環を形成することを表す。
例えば、置換基番号RO4とは、R32が水素原子であり、R33がイソプロピル基である組合せを表す。 Formula (XVI)
Figure 2019089711
[Wherein, R 32 and R 33 represent the same meaning as described above. ]
Wherein the combination of R 32 and R 33 is a combination as set forth in any of Substituent Nos. RO 1 to RO 130 shown below (hereinafter referred to as “compound of Substituent No. RO 1 to RO 130” Invention compounds RO1 to RO130, and the compounds of the present invention RO1 to RO130 are collectively referred to as the compound of the invention RO) can be obtained according to the method described in the above-mentioned production method.
The substituent numbers RO1 to RO130 represent a combination of R 32 and R 33 in the compound represented by the formula (XVI), and hereinafter referred to as [substituent number; R 32 , R 33 ] . However, in Substituent Nos. RO127 to RO129, R 32 and R 33 represent that they combine with each other to form a heterocycle.
For example, the substituent number RO4 represents a combination in which R 32 is a hydrogen atom and R 33 is an isopropyl group.

例えば、本発明化合物RO4とは、式(XVI)で表される化合物において置換基番号がRO4である化合物を意味し、式(XVI)で表される化合物において、R32が水素原子であり、R33がイソプロピル基である下記の化合物を表す。

Figure 2019089711
For example, the compound RO4 of the present invention means a compound represented by the formula (XVI) in which the substituent number is RO4, and in the compound represented by the formula (XVI), R 32 is a hydrogen atom, It represents the following compound wherein R 33 is an isopropyl group.
Figure 2019089711

[置換基番号;R32,R33]:[RO1;H,Me],[RO2;H,Et],[RO3;H,Pr],[RO4;H,i-Pr],[RO5;H,c-Pr],[RO6;H,Bu],[RO7;H,t-Bu],[RO8;H,c-PrCH2],[RO9;H,Ph],[RO10;H,Bn],[RO11;H,CF3CH2],[RO12;H,CF2HCH2],[RO13;H,CHCCH2],[RO14;H,MeCCCH2],[RO15;Me,Me],[RO16;Me,Et],[RO17;Me,Pr],[RO18;Me,i-Pr],[RO19;Me,c-Pr],[RO20;Me,Bu],[RO21;Me,t-Bu],[RO22;Me,c-PrCH2],[RO23;Me,Ph],[RO24;Me,Bn],[RO25;Me,CF3CH2],[RO26;Me,CF2HCH2],[RO27;Me,CHCCH2],[RO28;Me,MeCCCH2],[RO29;Et,Et],[RO30;Et,Pr],[RO31;Et,i-Pr],[RO32;Et,c-Pr],[RO33;Et,Bu],[RO34;Et,t-Bu],[RO35;Et,c-PrCH2],[RO36;Et,Ph],[RO37;Et,Bn],[RO38;Et,CF3CH2],[RO39;Et,CF2HCH2],[RO40;Et,CHCCH2],[RO41;Et,MeCCCH2],[RO42;Pr,Pr],[RO43;Pr,i-Pr],[RO44;Prc-Pr],[RO45;Pr,Bu],[RO46;Pr,t-Bu],[RO47;Pr,c-PrCH2],[RO48;Pr,Ph],[RO49;Pr,Bn],[RO50;Pr,CF3CH2],[RO51;Pr,CF2HCH2],[RO52;Pr,CHCCH2],[RO53;Pr,MeCCCH2],[RO54;i-Pr,i-Pr],[RO55;i-Pr,c-Pr],[RO56;i-Pr,Bu],[RO57;i-Pr,t-Bu],[RO58;i-Pr,c-PrCH2],[RO59;i-Pr,Ph],[RO60;i-Pr,Bn],[RO61;i-Pr,CF3CH2],[RO62;i-Pr,CF2HCH2],[RO63;i-Pr,CHCCH2],[RO64;i-Pr,MeCCCH2],[RO65;c-Pr,c-Pr],[RO66;c-Pr,Bu],[RO67;c-Pr,t-Bu],[RO68;c-Pr,c-PrCH2],[RO69;c-Pr,Ph],[RO70;c-Pr,Bn],[RO71;c-Pr,CF3CH2],[RO72;c-Pr,CF2HCH2],[RO73;c-Pr,CHCCH2],[RO74;c-Pr,MeCCCH2],[RO75;c-PrCH2,Bu],[RO76;c-PrCH2,t-Bu],[RO77;c-PrCH2,c-PrCH2],[RO78;c-PrCH2,Ph],[RO79;c-PrCH2,Bn],[RO80;c-PrCH2,CF3CH2],[RO81;c-PrCH2,CF2HCH2],[RO82;c-PrCH2,CHCCH2],[RO83;c-PrCH2,MeCCCH2],[RO84;CF3CH2,Bu],[RO85;CF3CH2,t-Bu],[RO86;CF3CH2,Ph],[RO87;CF3CH2,Bn],[RO88;CF3CH2,CF3CH2],[RO89;CF3CH2,CF2HCH2],[RO90;CF3CH2,CHCCH2],[RO91;CF3CH2,MeCCCH2],[RO92;CF2HCH2,Bu],[RO93;CF2HCH2,t-Bu],[RO94;CF2HCH2,Ph],[RO95;CF2HCH2,Bn],[RO96;CF2HCH2,CF2HCH2],[RO97;CF2HCH2,CHCCH2],[RO98;CF2HCH2,MeCCCH2],[RO99;MeOCH2,Me],[RO100;MeOCH2,Et],[RO101;MeOCH2,Pr],[RO102;MeOCH2,i-Pr],[RO103;MeOCH2,c-Pr],[RO104;MeOCH2,Bu],[RO105;MeOCH2,t-Bu],[RO106;MeOCH2,c-PrCH2],[RO107;MeOCH2,Ph],[RO108;MeOCH2,Bn],[RO109;MeOCH2,CF3CH2],[RO110;MeOCH2,CF2HCH2],[RO111;MeOCH2,CHCCH2],[RO112;MeOCH2,MeCCCH2],[RO113;EtOCH2,Me],[RO114;EtOCH2,Et],[RO115;EtOCH2,Pr],[RO116;EtOCH2,i-Pr],[RO117;EtOCH2,c-Pr],[RO118;EtOCH2,Bu],[RO119;EtOCH2,t-Bu],[RO120;EtOCH2,c-PrCH2],[RO121;EtOCH2,Ph],[RO122;EtOCH2,Bn],[RO123;EtOCH2,CF3CH2],[RO124;EtOCH2,CF2HCH2],[RO125;EtOCH2,CHCCH2],[RO126;EtOCH2,MeCCCH2],[RO127;CH2(CH2)2CH2],[RO128;CH2(CH2)3CH2],[RO129;CH2CH2OCH2CH2],[RO130;H,H] [Substituent number; R 32 , R 33 ]: [RO 1; H, Me], [RO 2; H, Et], [RO 3; H, Pr], [RO 4; H, i-Pr], [RO 5; , c-Pr], [RO 6; H, Bu], [RO 7; H, t-Bu], [RO 8; H, c-PrCH 2 ], [RO 9; H, Ph], [RO 10; H, Bn] , [RO 11; H, CF 3 CH 2 ], [RO 12; H, CF 2 HCH 2 ], [RO 13; H, CHCCH 2 ], [RO 14; H, MeCCCH 2 ], [RO 15; Me, Me], [RO RO16; Me, Et], [RO17; Me, Pr], [RO18; Me, i-Pr], [RO19; Me, c-Pr], [RO20; Me, Bu], [RO21; Me, t- Bu], [RO22; Me, c-PrCH 2], [RO23; Me, Ph], [RO24; Me, Bn], [RO25; Me, CF 3 CH 2], [RO26; Me, CF 2 HCH 2 ], [RO27; Me, CHCCH 2], [RO28; Me, MeCCCH 2], [RO29; Et, Et], [RO30; Et, Pr], [RO31; Et, i-Pr], [RO32; Et , c-Pr], [RO 33; Et, Bu], [RO 34; Et, t-Bu], [RO 35; Et, c-PrCH 2 ], [RO 36; Et, Ph], [RO 37; Et, Bn] , [RO38; Et, CF 3 CH 2], [RO39; Et, CF 2 HCH 2], [RO40; Et, CHCCH 2], [RO41; Et, MeCCCH 2], [RO42; Pr, Pr], [ RO 43; Pr, i-Pr], [RO 44; Prc-Pr], [RO 45; Pr, Bu], [RO 46; Pr, t-Bu], [RO 47; Pr, c-PrCH 2 ], [RO 48; , Ph], [RO 49; Pr, Bn], [RO 50; Pr, CF 3 CH 2 ], [RO 51; Pr, CF 2 HCH 2 ], [RO 52; Pr, CHCCH 2 ], [RO 53; Pr, MeCCCH 2 ], [RO 54; i-Pr, i-Pr], [RO 55; i-Pr, c-Pr], [RO 56; i-Pr, Bu], [RO 57; i-Pr, t-Bu], [RO 58 i-Pr, c-PrCH 2 ], [RO 59; i-Pr, Ph], [RO 60; i-Pr, Bn], [RO 61; i-Pr, CF 3 CH 2 ], [RO 62; i-Pr, CF 2 HCH 2 ], [RO 63; i-Pr, CHCCH 2 ], [RO 64; i-Pr, MeCCCH 2 ], [RO 65; c-Pr, c-Pr] , [RO 66; c-Pr, Bu], [RO 67; c-Pr, t-Bu], [RO 68; c-Pr, c-PrCH 2 ], [RO 69; c-Pr, Ph], [RO 70; -Pr, Bn], [RO71; c-Pr, CF 3 CH 2], [RO72; c-Pr, CF 2 HCH 2], [RO73; c-Pr, CHCCH 2], [RO74; c-Pr, MeCCCH 2], [RO75; c -PrCH 2, Bu], [RO76; c-PrCH 2, t-Bu], [RO77; c-PrCH 2, c-PrCH 2], [RO78; c-PrCH 2, Ph], [RO79; c- PrCH 2, Bn], [RO80; c-PrCH 2, CF 3 CH 2], [RO81; c-PrCH 2, CF 2 HCH 2], [RO82; c-PrCH 2, CHCCH 2], [RO83; c -PrCH 2, MeCCCH 2], [RO84; CF 3 CH 2, Bu], [RO85; CF 3 CH 2, t-Bu], [RO86; CF 3 CH 2, Ph] , [RO 87; CF 3 CH 2 , Bn], [RO 88; CF 3 CH 2 , CF 3 CH 2 ], [RO 89; CF 3 CH 2 , CF 2 HCH 2 ], [RO 90; CF 3 CH 2 , CHCCH 2 ], [RO91; CF 3 CH 2, MeCCCH 2], [RO92; CF 2 HCH 2, Bu], [RO93; CF 2 HCH 2, t-Bu], [RO94; CF 2 HCH 2, Ph], [ RO95; CF 2 HCH 2, Bn ], [RO96; CF 2 HCH 2, CF 2 HCH 2], [RO97; CF 2 HCH 2, CHCCH 2], [RO98; CF 2 HCH 2, MeCCCH 2], [RO99 ; MeOCH 2, Me], [ RO100; MeOCH 2, Et], [RO101; MeOCH 2, Pr], [RO102; MeOCH 2, i-Pr], [RO103; MeOCH 2, c-Pr], [RO104; MeOCH 2 , Bu], [RO 105; MeOCH 2 , t-Bu], [RO106 ; MeOCH 2, c-PrCH 2], [RO107; MeOCH 2, Ph], [RO108; MeOCH 2, Bn], [RO109; MeOCH 2, CF 3 CH 2], [RO110 ; MeOCH 2, CF 2 HCH 2 ], [RO111; MeOCH 2, CHCCH 2], [RO112; MeOCH 2, MeCCCH 2], [RO113; EtOCH 2, Me], [RO114; EtOCH 2, Et], [RO115 ; EtOCH 2, Pr], [ RO116; EtOCH 2, i-Pr], [RO117; EtOCH 2, c-Pr], [RO118; EtOCH 2, Bu], [RO119; EtOCH 2, t-Bu], [ RO120; EtOCH 2, c-PrCH 2], [RO121; EtOCH 2, Ph], [RO122; EtOCH 2, Bn], [RO123; EtOCH 2, CF 3 CH 2], [RO124; EtOCH 2, CF 2 HCH 2], [RO125; EtOCH 2 , CHCCH 2], [RO126; EtOCH 2, MeCCCH 2], [RO127; CH 2 (CH 2) 2 CH 2], [RO128; CH 2 (CH 2) 3 CH 2] , [rO129; CH 2 CH 2 OCH 2 CH 2], [RO130; H, H]

式(XVII)

Figure 2019089711
〔式中、R32及びR33は上記と同じ意味を表す。〕
で表される化合物において、R32及びR33の組合わせが下記に示される置換基番号RP1〜RP130のいずれかに記載の組合わせである化合物(以下、置換基番号RP1〜RP130の化合物を本発明化合物RP1〜RP130と表し、本発明化合物RP1〜RP130をまとめて本発明化合物RPと表す)は、上記の製造法に記載の方法に準じて得ることができる。
なお、置換基番号RP1〜RP130とは、式(XVII)で表される化合物における、R32及びR33の組合せを表すものであり、以下、[置換基番号;R32,R33]と記す。ただし、置換基番号RP127〜RP129においては、R32とR33とが、互いに結合してヘテロ環を形成することを表す。
例えば、置換基番号RP4とは、R32が水素原子であり、R33がイソプロピル基である組合せを表す。 Formula (XVII)
Figure 2019089711
[Wherein, R 32 and R 33 represent the same meaning as described above. ]
Wherein the combination of R 32 and R 33 is a combination as set forth in any one of Substituent Nos. RP 1 to RP 130 shown below (hereinafter referred to as “compound of Substituent No. RP 1 to RP 130” Invention compounds RP1 to RP130, and the compounds of the present invention RP1 to RP130 are collectively referred to as the compound of the invention RP) can be obtained according to the method described in the above-mentioned production method.
In addition, the substituent numbers RP1 to RP130 represent a combination of R 32 and R 33 in the compound represented by the formula (XVII), and hereinafter referred to as [substituent number: R 32 , R 33 ] . However, in Substituent Nos. RP127 to RP129, R 32 and R 33 represent that they combine with each other to form a heterocycle.
For example, the substituent number RP4 represents a combination in which R 32 is a hydrogen atom and R 33 is an isopropyl group.

例えば、本発明化合物RP4とは、式(XVII)で表される化合物において置換基番号がRP4である化合物を意味し、式(XVII)で表される化合物において、R32が水素原子であり、R33がイソプロピル基である下記化合物を表す。

Figure 2019089711
For example, the compound RP4 of the present invention means a compound represented by the formula (XVII) in which the substituent number is RP4, and in the compound represented by the formula (XVII), R 32 is a hydrogen atom, Represents the following compound wherein R 33 is an isopropyl group.
Figure 2019089711

[置換基番号;R32,R33]:[RP1;H,Me],[RP2;H,Et],[RP3;H,Pr],[RP4;H,i-Pr],[RP5;H,c-Pr],[RP6;H,Bu],[RP7;H,t-Bu],[RP8;H,c-PrCH2],[RP9;H,Ph],[RP10;H,Bn],[RP11;H,CF3CH2],[RP12;H,CF2HCH2],[RP13;H,CHCCH2],[RP14;H,MeCCCH2],[RP15;Me,Me],[RP16;Me,Et],[RP17;Me,Pr],[RP18;Me,i-Pr],[RP19;Me,c-Pr],[RP20;Me,Bu],[RP21;Me,t-Bu],[RP22;Me,c-PrCH2],[RP23;Me,Ph],[RP24;Me,Bn],[RP25;Me,CF3CH2],[RP26;Me,CF2HCH2],[RP27;Me,CHCCH2],[RP28;Me,MeCCCH2],[RP29;Et,Et],[RP30;Et,Pr],[RP31;Et,i-Pr],[RP32;Et,c-Pr],[RP33;Et,Bu],[RP34;Et,t-Bu],[RP35;Et,c-PrCH2],[RP36;Et,Ph],[RP37;Et,Bn],[RP38;Et,CF3CH2],[RP39;Et,CF2HCH2],[RP40;Et,CHCCH2],[RP41;Et,MeCCCH2],[RP42;Pr,Pr],[RP43;Pr,i-Pr],[RP44;Prc-Pr],[RP45;Pr,Bu],[RP46;Pr,t-Bu],[RP47;Pr,c-PrCH2],[RP48;Pr,Ph],[RP49;Pr,Bn],[RP50;Pr,CF3CH2],[RP51;Pr,CF2HCH2],[RP52;Pr,CHCCH2],[RP53;Pr,MeCCCH2],[RP54;i-Pr,i-Pr],[RP55;i-Pr,c-Pr],[RP56;i-Pr,Bu],[RP57;i-Pr,t-Bu],[RP58;i-Pr,c-PrCH2],[RP59;i-Pr,Ph],[RP60;i-Pr,Bn],[RP61;i-Pr,CF3CH2],[RP62;i-Pr,CF2HCH2],[RP63;i-Pr,CHCCH2],[RP64;i-Pr,MeCCCH2],[RP65;c-Pr,c-Pr],[RP66;c-Pr,Bu],[RP67;c-Pr,t-Bu],[RP68;c-Pr,c-PrCH2],[RP69;c-Pr,Ph],[RP70;c-Pr,Bn],[RP71;c-Pr,CF3CH2],[RP72;c-Pr,CF2HCH2],[RP73;c-Pr,CHCCH2],[RP74;c-Pr,MeCCCH2],[RP75;c-PrCH2,Bu],[RP76;c-PrCH2,t-Bu],[RP77;c-PrCH2,c-PrCH2],[RP78;c-PrCH2,Ph],[RP79;c-PrCH2,Bn],[RP80;c-PrCH2,CF3CH2],[RP81;c-PrCH2,CF2HCH2],[RP82;c-PrCH2,CHCCH2],[RP83;c-PrCH2,MeCCCH2],[RP84;CF3CH2,Bu],[RP85;CF3CH2,t-Bu],[RP86;CF3CH2,Ph],[RP87;CF3CH2,Bn],[RP88;CF3CH2,CF3CH2],[RP89;CF3CH2,CF2HCH2],[RP90;CF3CH2,CHCCH2],[RP91;CF3CH2,MeCCCH2],[RP92;CF2HCH2,Bu],[RP93;CF2HCH2,t-Bu],[RP94;CF2HCH2,Ph],[RP95;CF2HCH2,Bn],[RP96;CF2HCH2,CF2HCH2],[RP97;CF2HCH2,CHCCH2],[RP98;CF2HCH2,MeCCCH2],[RP99;MeOCH2,Me],[RP100;MeOCH2,Et],[RP101;MeOCH2,Pr],[RP102;MeOCH2,i-Pr],[RP103;MeOCH2,c-Pr],[RP104;MeOCH2,Bu],[RP105;MeOCH2,t-Bu],[RP106;MeOCH2,c-PrCH2],[RP107;MeOCH2,Ph],[RP108;MeOCH2,Bn],[RP109;MeOCH2,CF3CH2],[RP110;MeOCH2,CF2HCH2],[RP111;MeOCH2,CHCCH2],[RP112;MeOCH2,MeCCCH2],[RP113;EtOCH2,Me],[RP114;EtOCH2,Et],[RP115;EtOCH2,Pr],[RP116;EtOCH2,i-Pr],[RP117;EtOCH2,c-Pr],[RP118;EtOCH2,Bu],[RP119;EtOCH2,t-Bu],[RP120;EtOCH2,c-PrCH2],[RP121;EtOCH2,Ph],[RP122;EtOCH2,Bn],[RP123;EtOCH2,CF3CH2],[RP124;EtOCH2,CF2HCH2],[RP125;EtOCH2,CHCCH2],[RP126;EtOCH2,MeCCCH2],[RP127;CH2(CH2)2CH2],[RP128;CH2(CH2)3CH2],[RP129;CH2CH2OCH2CH2],[RP130;H,H] [Substituent number; R 32 , R 33 ]: [RP1; H, Me], [RP2; H, Et], [RP3; H, Pr], [RP4; H, i-Pr], [RP5; H , c-Pr], [RP6 ; H, Bu], [RP7; H, t-Bu], [RP8; H, c-PrCH 2], [RP9; H, Ph], [RP10; H, Bn] , [RP11; H, CF 3 CH 2], [RP12; H, CF 2 HCH 2], [RP13; H, CHCCH 2], [RP14; H, MeCCCH 2], [RP15; Me, Me], [ RP16; Me, Et], [RP17; Me, Pr], [RP18; Me, i-Pr], [RP19; Me, c-Pr], [RP20; Me, Bu], [RP21; Me, t- Bu], [RP22; Me, c-PrCH 2], [RP23; Me, Ph], [RP24; Me, Bn], [RP25; Me, CF 3 CH 2], [RP26; Me, CF 2 HCH 2 ], [RP27; Me, CHCCH 2], [RP28; Me, MeCCCH 2], [RP29; Et, Et], [RP30; Et, Pr], [RP31; Et, i-Pr], [RP32; Et , c-Pr], [RP33 ; Et, Bu], [RP34; Et, t-Bu], [rP35; Et, c-PrCH 2], [RP36; Et, Ph], [RP37; Et, Bn] , [RP 38; Et, CF 3 CH 2 ], [RP 39; Et, CF 2 HCH 2 ], [RP 40; Et, CHCCH 2 ], [RP 41; Et, MeCCCH 2 ], [RP 42; Pr, Pr], [RP 38; RP43; Pr, i-Pr] , [RP44; Prc-Pr], [RP45; Pr, Bu], [RP46; Pr, t-Bu], [RP47; Pr, c-PrCH 2], [RP48; Pr , Ph], [RP 49; Pr, Bn], [RP 50; Pr, CF 3 CH 2 ], [RP 51; Pr, CF 2 HCH 2 ], [RP 52; Pr, CHCCH 2 ], [RP 53; Pr, MeCCCH 2 ], [RP54; i-Pr, i-Pr], [RP55; i-Pr, c-Pr], [RP56; i-Pr, Bu], [RP57; i-Pr, t-Bu], [RP58] ; i-Pr, c-PrCH 2], [RP59; i-Pr, Ph], [RP60; i-Pr, Bn], [RP61; i-Pr, CF 3 CH 2], [RP62; i -Pr, CF 2 HCH 2], [RP63; i-Pr, CHCCH 2], [RP64; i-Pr, MeCCCH 2], [RP65; c-Pr, c-Pr] , [RP 66; c-Pr, Bu], [RP 67; c-Pr, t-Bu], [RP 68; c-Pr, c-PrCH 2 ], [RP 69; c-Pr, Ph], [RP 70; -Pr, Bn], [RP71; c-Pr, CF 3 CH 2], [RP72; c-Pr, CF 2 HCH 2], [RP73; c-Pr, CHCCH 2], [RP74; c-Pr, MeCCCH 2], [RP75; c -PrCH 2, Bu], [RP76; c-PrCH 2, t-Bu], [RP77; c-PrCH 2, c-PrCH 2], [RP78; c-PrCH 2, Ph], [RP79; c- PrCH 2, Bn], [RP80; c-PrCH 2, CF 3 CH 2], [RP81; c-PrCH 2, CF 2 HCH 2], [RP82; c-PrCH 2, CHCCH 2], [RP83; c -PrCH 2, MeCCCH 2], [RP84; CF 3 CH 2, Bu], [RP85; CF 3 CH 2, t-Bu], [RP86; CF 3 CH 2, Ph] , [RP 87; CF 3 CH 2 , Bn], [RP 88; CF 3 CH 2 , CF 3 CH 2 ], [RP 89; CF 3 CH 2 , CF 2 HCH 2 ], [RP 90; CF 3 CH 2 , CHCCH 2 ], [RP91; CF 3 CH 2, MeCCCH 2], [RP92; CF 2 HCH 2, Bu], [RP93; CF 2 HCH 2, t-Bu], [RP94; CF 2 HCH 2, Ph], [ RP95; CF 2 HCH 2, Bn ], [RP96; CF 2 HCH 2, CF 2 HCH 2], [RP97; CF 2 HCH 2, CHCCH 2], [RP98; CF 2 HCH 2, MeCCCH 2], [RP99 ; MeOCH 2, Me], [ RP100; MeOCH 2, Et], [RP101; MeOCH 2, Pr], [RP102; MeOCH 2, i-Pr], [RP103; MeOCH 2, c-Pr], [RP104; MeOCH 2 , Bu], [RP 105; MeOCH 2 , t-Bu], [RP106 ; MeOCH 2, c-PrCH 2], [RP107; MeOCH 2, Ph], [RP108; MeOCH 2, Bn], [RP109; MeOCH 2, CF 3 CH 2], [RP110 ; MeOCH 2, CF 2 HCH 2 ], [RP111; MeOCH 2, CHCCH 2], [RP112; MeOCH 2, MeCCCH 2], [RP113; EtOCH 2, Me], [RP114; EtOCH 2, Et], [RP115 ; EtOCH 2, Pr], [ RP116; EtOCH 2, i-Pr], [RP117; EtOCH 2, c-Pr], [RP118; EtOCH 2, Bu], [RP119; EtOCH 2, t-Bu], [ RP120; EtOCH 2, c-PrCH 2], [RP121; EtOCH 2, Ph], [RP122; EtOCH 2, Bn], [RP123; EtOCH 2, CF 3 CH 2], [RP124; EtOCH 2, CF 2 HCH 2 ], [RP 125; EtOCH 2 , CHCCH 2 ], [RP 126; EtOCH 2 , MeCCCH 2 ], [RP 127; CH 2 (CH 2 ) 2 CH 2 ], [RP 128; CH 2 (CH 2 ) 3 CH 2 ] , [RP129; CH 2 CH 2 OCH 2 CH 2 ], [RP 130; H, H]

式(XVIII)

Figure 2019089711
〔式中、R21、R22及びR25は上記と同じ意味を表す。〕
で表される化合物において、R21、R22及びR25の組合わせが下記に示される置換基番号RQ1〜RQ45のいずれかに記載の組合わせである化合物(以下、置換基番号RQ1〜RQ45の化合物を本発明化合物RQ1〜RQ45と表し、本発明化合物RQ1〜RQ45をまとめて本発明化合物RQと表す)は、上記の製造法に記載の方法に準じて得ることができる。
なお、置換基番号RQ1〜RQ45とは、式(XVIII)で表される化合物における、R21、R22及びR25の組合わせを表すものであり、以下、[置換基番号;R21,R22,R25]と記す。
例えば、置換基番号RQ4とは、R21及びR22が水素原子であり、R25がイソプロピル基である組合せを表す。 Formula (XVIII)
Figure 2019089711
[Wherein, R 21 , R 22 and R 25 represent the same meaning as described above. ]
Wherein the combination of R 21 , R 22 and R 25 is a combination as set forth in any of the substituent numbers RQ 1 to R 45 shown below (hereinafter referred to as “substituent numbers RQ 1 to RQ 45 The compounds are represented as the compounds of the present invention RQ1 to RQ45, and the compounds of the present invention RQ1 to RQ45 are collectively referred to as the compounds of the present invention RQ) can be obtained according to the method described in the above-mentioned production method.
In addition, the substituent numbers RQ1 to R45 represent a combination of R 21 , R 22 and R 25 in the compound represented by the formula (XVIII), and hereinafter, [Substituent number: R 21 , R 22 , R 25 ].
For example, the substituent number RQ4 represents a combination in which R 21 and R 22 are a hydrogen atom and R 25 is an isopropyl group.

例えば、本発明化合物RQ4とは、式(XVIII)で表される化合物において置換基番号がRQ4である化合物を意味し、式(XVIII)で表される化合物において、R21及びR22が水素原子であり、R25がイソプロピル基である下記化合物を表す。

Figure 2019089711
For example, the compound of the present invention RQ4 means a compound represented by the formula (XVIII) in which the substituent number is RQ4, and in the compound represented by the formula (XVIII), R 21 and R 22 are a hydrogen atom And the following compounds in which R 25 is an isopropyl group.
Figure 2019089711

[置換基番号;R21,R22,R25]:[RQ1;H,H,Me],[RQ2;H,H,Et],[RQ3;H,H,Pr],[RQ4;H,H,i-Pr],[RQ5;H,H,c-Pr],[RQ6;H,H,Bu],[RQ7;H,H,t-Bu],[RQ8;H,H,c-PrCH2],[RQ9;H,H,Ph],[RQ10;H,H,Bn],[RQ11;H,H,CF3],[RQ12;H,H,CF3CH2],[RQ13;H,H,CF3CF2],[RQ14;H,H,CF2H],[RQ15;H,H,CF2HCH2],[RQ16;F,H,Me],[RQ17;F,H,Et],[RQ18;F,H,Pr],[RQ19;F,H,i-Pr],[RQ20;F,H,c-Pr],[RQ21;F,H,Bu],[RQ22;F,H,t-Bu],[RQ23;F,H,c-PrCH2],[RQ24;F,H,Ph],[RQ25;F,H,Bn],[RQ26;F,H,CF3],[RQ27;F,H,CF3CH2],[RQ28;F,H,CF3CF2],[RQ29;F,H,CF2H],[RQ30;F,H,CF2HCH2],[RQ31;H,F,Me],[RQ32;H,F,Et],[RQ33;H,F,Pr],[RQ34;H,F,i-Pr],[RQ35;H,F,c-Pr],[RQ36;H,F,Bu],[RQ37;H,F,t-Bu],[RQ38;H,F,c-PrCH2],[RQ39;H,F,Ph],[RQ40;H,F,Bn],[RQ41;H,F,CF3],[RQ42;H,F,CF3CH2],[RQ43;H,F,CF3CF2],[RQ44;H,F,CF2H],[RQ45;H,F,CF2HCH2] [Substituent number; R 21 , R 22 , R 25 ]: [RQ1; H, H, Me], [RQ 2; H, H, Et], [RQ 3; H, H, Pr], [RQ 4; H, H, i-Pr], [RQ 5; H, H, c-Pr], [RQ 6; H, H, Bu], [RQ 7; H, H, t-Bu], [RQ 8; H, H, c- PrCH 2], [RQ9; H , H, Ph], [RQ10; H, H, Bn], [RQ11; H, H, CF 3], [RQ12; H, H, CF 3 CH 2], [RQ13 ; H, H, CF 3 CF 2], [RQ14; H, H, CF 2 H], [RQ15; H, H, CF 2 HCH 2], [RQ16; F, H, Me], [RQ17; F , H, Et], [RQ 18; F, H, Pr], [RQ 19; F, H, i-Pr], [RQ 20; F, H, c-Pr], [RQ 21; F, H, Bu], [RQ 22; F, H, t-Bu], [RQ 23; F, H, c-PrCH 2 ], [RQ 24; F, H, Ph], [RQ 25; F, H, Bn], [RQ 26; F, H, CF 3 ], [RQ 27; F, H, CF 3 CH 2 ], [RQ 28; F, H, CF 3 CF 2 ], [RQ 29; F, H, CF 2 H], [RQ 30; F, H , CF 2 HCH 2 ], [RQ 31; H, F, Me], [RQ 32; H, F, Et], [RQ 33; H, F, Pr], [RQ 34; H, F, i-Pr], [RQ H, F, c-Pr], [RQ 36; H, F, Bu], [RQ 37; H, F, t-Bu], [RQ 38; H, F, c-PrCH 2 ], [RQ 39; H , F, Ph], [RQ 40; H, F, Bn], [RQ 41; H, F, CF 3 ], [RQ 42; H, F, CF 3 CH 2 ], [RQ 43; H, F, CF 3 CF 2 ], [RQ 44; H, F, CF 2 H], [RQ 45; H, F, CF 2 HCH 2 ]

式(XIX)

Figure 2019089711
〔式中、R21、R22及び25は上記と同じ意味を表す。〕
で表される化合物において、R21、R22及びR25の組合わせが下記に示される置換基番号RR1〜RR45のいずれかに記載の組合わせである化合物(以下、置換基番号RR1〜RR45の化合物を本発明化合物RR1〜RR45と表し、本発明化合物RR1〜RR45をまとめて本発明化合物RRと表す)は、上記の製造法に記載の方法に準じて得ることができる。
なお、置換基番号RR1〜RR45とは、式(XIX)で表される化合物における、R21、R22及びR25の組合わせを表すものであり、以下、[置換基番号;R21,R22,R25]と記す。
例えば、置換基番号RR4とは、R21及びR22が水素原子であり、R25がイソプロピル基である組合せを表す。 Formula (XIX)
Figure 2019089711
[Wherein, R 21 , R 22 and 25 represent the same meaning as described above. ]
Wherein the combination of R 21 , R 22 and R 25 is a combination as set forth in any one of Substituent Nos. RR 1 to RR 45 shown below (hereinafter referred to as Substituent Nos. RR 1 to RR 45 The compounds are represented by the compounds of the present invention RR1 to RR45, and the compounds of the present invention RR1 to RR45 are collectively referred to as the compound of the present invention RR) can be obtained according to the method described in the above-mentioned production method.
In addition, the substituent numbers RR1 to RR45 represent a combination of R 21 , R 22 and R 25 in the compound represented by the formula (XIX), and the [substituent number; R 21 , R] 22 , R 25 ].
For example, the substituent number RR4 represents a combination in which R 21 and R 22 are a hydrogen atom and R 25 is an isopropyl group.

例えば、本発明化合物RR4とは、式(XIX)で表される化合物において置換基番号がRR4である化合物を意味し、式(XIX)で表される化合物において、R21及びR22が水素原子であり、R25がイソプロピル基である下記化合物を表す。

Figure 2019089711
For example, the present compound RR4, means a compound substituent number is RR4 in the compound represented by the formula (XIX), in the compounds represented by the formula (XIX), R 21 and R 22 is a hydrogen atom And the following compounds in which R 25 is an isopropyl group.
Figure 2019089711

[置換基番号;R21,R22,R25]:[RR1;H,H,Me],[RR2;H,H,Et],[RR3;H,H,Pr],[RR4;H,H,i-Pr],[RR5;H,H,c-Pr],[RR6;H,H,Bu],[RR7;H,H,t-Bu],[RR8;H,H,c-PrCH2],[RR9;H,H,Ph],[RR10;H,H,Bn],[RR11;H,H,CF3],[RR12;H,H,CF3CH2],[RR13;H,H,CF3CF2],[RR14;H,H,CF2H],[RR15;H,H,CF2HCH2],[RR16;F,H,Me],[RR17;F,H,Et],[RR18;F,H,Pr],[RR19;F,H,i-Pr],[RR20;F,H,c-Pr],[RR21;F,H,Bu],[RR22;F,H,t-Bu],[RR23;F,H,c-PrCH2],[RR24;F,H,Ph],[RR25;F,H,Bn],[RR26;F,H,CF3],[RR27;F,H,CF3CH2],[RR28;F,H,CF3CF2],[RR29;F,H,CF2H],[RR30;F,H,CF2HCH2],[RR31;H,F,Me],[RR32;H,F,Et],[RR33;H,F,Pr],[RR34;H,F,i-Pr],[RR35;H,F,c-Pr],[RR36;H,F,Bu],[RR37;H,F,t-Bu],[RR38;H,F,c-PrCH2],[RR39;H,F,Ph],[RR40;H,F,Bn],[RR41;H,F,CF3],[RR42;H,F,CF3CH2],[RR43;H,F,CF3CF2],[RR44;H,F,CF2H],[RR45;H,F,CF2HCH2] [Substituent group number; R 21, R 22, R 25]: [RR1; H, H, Me], [RR2; H, H, Et], [RR3; H, H, Pr], [RR4; H, H, i-Pr], [RR 5; H, H, c-Pr], [RR 6; H, H, Bu], [RR 7; H, H, t-Bu], [RR 8; H, H, c- PrCH 2 ], [RR 9; H, H, Ph], [RR 10; H, H, Bn], [RR 11; H, H, CF 3 ], [RR 12; H, H, CF 3 CH 2 ], [RR 13 ; H, H, CF 3 CF 2], [RR14; H, H, CF 2 H], [RR15; H, H, CF 2 HCH 2], [RR16; F, H, Me], [RR17; F , H, Et], [RR 18; F, H, Pr], [RR 19; F, H, i-Pr], [RR 20; F, H, c-Pr], [RR 21; F, H, Bu], [RR22; F, H, t -Bu], [RR23; F, H, c-PrCH 2], [RR24; F, H, Ph], [RR25; F, H, Bn], [RR26; F, H, CF 3], [RR27 ; F, H, CF 3 CH 2], [RR28; F, H, CF 3 CF 2], [RR29; F, H, CF 2 H], [RR30; F, H , CF 2 HCH 2 ], [RR 31; H, F, Me], [RR 32; H, F, Et], [RR 33; H, F, Pr], [RR 34; H, F, i-Pr], [[ H, F, c-Pr], [RR 36; H, F, Bu], [RR 37; H, F, t-Bu], [RR 38; H, F, c-PrCH 2 ], [RR 39; H , F, Ph], [RR 40; H, F, Bn], [RR 41; H, F, CF 3 ], [RR 42; H, F, CF 3 CH 2 ], [RR 43; H, F, CF 3 CF 2 ], [RR 44; H, F, CF 2 H], [RR 45; H, F, CF 2 HCH 2 ]

式(XX)

Figure 2019089711
〔式中、R21及びR25は上記と同じ意味を表し、R27は水素原子又はフッ素原子を表す。〕
で表される化合物において、R21、R27及びR25の組合わせが下記に示される置換基番号RS1〜RS45のいずれかに記載の組合わせである化合物(以下、置換基番号RS1〜RS45の化合物を本発明化合物RS1〜RS45と表し、本発明化合物RS1〜RS45をまとめて本発明化合物RSと表す)は、上記の製造法に記載の方法に準じて得ることができる。
なお、置換基番号RS1〜RS45とは、式(XX)で表される化合物における、R21、R27及びR25の組合わせを表すものであり、以下、[置換基番号;R21,R27,R25]と記す。
例えば、置換基番号RS4とは、R21及びR27が水素原子であり、R25がイソプロピル基である組合せを表す。 Formula (XX)
Figure 2019089711
[Wherein, R 21 and R 25 have the same meaning as described above, and R 27 represents a hydrogen atom or a fluorine atom. ]
Wherein the combination of R 21 , R 27 and R 25 is a combination as described in any one of the substituent numbers RS 1 to RS 45 shown below (hereinafter, referred to as substituent numbers RS 1 to RS 45 The compounds are referred to as the present compounds RS1 to RS45, and the present compounds RS1 to RS45 are collectively referred to as the present compound RS)) can be obtained according to the method described in the above-mentioned production method.
Note that the substituent number RS1~RS45, in the compound of formula (XX), and represents the combination of R 21, R 27 and R 25, below, Substituent group number; R 21, R 27 , R 25 ].
For example, the substituent number RS4 represents a combination in which R 21 and R 27 are a hydrogen atom and R 25 is an isopropyl group.

例えば、本発明化合物RS4とは、式(XX)で表される化合物において置換基番号がRS4である化合物を意味し、式(XX)で表される化合物において、R21及びR27が水素原子であり、R25がイソプロピル基である下記化合物を表す。

Figure 2019089711
For example, the compound RS4 of the present invention means a compound represented by the formula (XX) in which the substituent number is RS4, and in the compound represented by the formula (XX), R 21 and R 27 are a hydrogen atom And the following compounds in which R 25 is an isopropyl group.
Figure 2019089711

[置換基番号;R21,R27,R25]:[RS1;H,H,Me],[RS2;H,H,Et],[RS3;H,H,Pr],[RS4;H,H,i-Pr],[RS5;H,H,c-Pr],[RS6;H,H,Bu],[RS7;H,H,t-Bu],[RS8;H,H,c-PrCH2],[RS9;H,H,Ph],[RS10;H,H,Bn],[RS11;H,H,CF3],[RS12;H,H,CF3CH2],[RS13;H,H,CF3CF2],[RS14;H,H,CF2H],[RS15;H,H,CF2HCH2],[RS16;F,H,Me],[RS17;F,H,Et],[RS18;F,H,Pr],[RS19;F,H,i-Pr],[RS20;F,H,c-Pr],[RS21;F,H,Bu],[RS22;F,H,t-Bu],[RS23;F,H,c-PrCH2],[RS24;F,H,Ph],[RS25;F,H,Bn],[RS26;F,H,CF3],[RS27;F,H,CF3CH2],[RS28;F,H,CF3CF2],[RS29;F,H,CF2H],[RS30;F,H,CF2HCH2],[RS31;H,F,Me],[RS32;H,F,Et],[RS33;H,F,Pr],[RS34;H,F,i-Pr],[RS35;H,F,c-Pr],[RS36;H,F,Bu],[RS37;H,F,t-Bu],[RS38;H,F,c-PrCH2],[RS39;H,F,Ph],[RS40;H,F,Bn],[RS41;H,F,CF3],[RS42;H,F,CF3CH2],[RS43;H,F,CF3CF2],[RS44;H,F,CF2H],[RS45;H,F,CF2HCH2] [Substituent group number; R 21, R 27, R 25]: [RS1; H, H, Me], [RS2; H, H, Et], [RS3; H, H, Pr], [RS4; H, H, i-Pr], [RS 5; H, H, c-Pr], [RS 6; H, H, Bu], [RS 7; H, H, t-Bu], [RS 8; H, H, c- PrCH 2 ], [RS 9; H, H, Ph], [RS 10; H, H, Bn], [RS 11; H, H, CF 3 ], [RS 12; H, H, CF 3 CH 2 ], [RS 13 ; H, H, CF 3 CF 2], [RS14; H, H, CF 2 H], [RS15; H, H, CF 2 HCH 2], [RS16; F, H, Me], [RS17; F , H, Et], [RS 18; F, H, Pr], [RS 19; F, H, i-Pr], [RS 20; F, H, c-Pr], [RS 21; F, H, Bu], [RS22; F, H, t-Bu], [RS 23; F, H, c-PrCH 2 ], [RS 24; F, H, Ph], [RS 25; F, H, Bn], [RS 26; F, H, CF 3 ], [RS 27; F, H, CF 3 CH 2 ], [RS 28; F, H, CF 3 CF 2 ], [RS 29; F, H, CF 2 H], [RS 30; F, H , CF 2 HCH 2 ], [RS 31; H, F, Me], [RS 32; H, F, Et], [RS 33; H, F, Pr], [RS 34; H, F, i-Pr], [[ RS 35; H, F, c-Pr], [RS 36; H, F, Bu], [RS 37; H, F, t-Bu], [RS 38; H, F, c-PrCH 2 ], [RS 39; H , F, Ph], [RS 40; H, F, Bn], [RS 41; H, F, CF 3 ], [RS 42; H, F, CF 3 CH 2 ], [RS 43; H, F, CF 3 CF 2 ], [RS 44; H, F, CF 2 H], [RS 45; H, F, CF 2 HCH 2 ]

式(XXI)

Figure 2019089711
〔式中、R21、R25及びR27は上記と同じ意味を表す。〕
で表される化合物において、R21、R27及びR25の組合わせが下記に示される置換基番号RT1〜RT45のいずれかに記載の組合わせである化合物(以下、置換基番号RT1〜RT45の化合物を本発明化合物RT1〜RT45と表し、本発明化合物RT1〜RT45をまとめて本発明化合物RTと表す)は、上記の製造法に記載の方法に準じて得ることができる。
なお、置換基番号RT1〜RT45とは、式(XXI)で表される化合物における、R21、R27及びR25の組合わせを表すものであり、以下、[置換基番号;R21,R27,R25]と記す。
例えば、置換基番号RT4とは、R21及びR27が水素原子であり、R25がイソプロピル基である組合せを表す。 Formula (XXI)
Figure 2019089711
[Wherein, R 21 , R 25 and R 27 represent the same meaning as described above. ]
Wherein the combination of R 21 , R 27 and R 25 is a combination as set forth in any one of Substituent Nos. RT 1 to RT 45 shown below (hereinafter referred to as Substituent Nos. RT 1 to RT 45 The compounds are referred to as present compounds RT1 to RT45, and the present compounds RT1 to RT45 are collectively referred to as present compound RT)) can be obtained according to the method described in the above-mentioned production method.
Note that the substituent number RT1~RT45, in the compound of formula (XXI), and represents the combination of R 21, R 27 and R 25, below, Substituent group number; R 21, R 27 , R 25 ].
For example, the substituent number RT4 represents a combination in which R 21 and R 27 are a hydrogen atom and R 25 is an isopropyl group.

例えば、本発明化合物RT4とは、式(XXI)で表される化合物において置換基番号がRT4である化合物を意味し、式(XXI)で表される化合物において、R21及びR27が水素原子であり、R25がイソプロピル基である下記化合物を表す。

Figure 2019089711
For example, the compound RT4 of the present invention means a compound having a substituent number of RT4 in the compound represented by the formula (XXI), and in the compound represented by the formula (XXI), R 21 and R 27 are a hydrogen atom And the following compounds in which R 25 is an isopropyl group.
Figure 2019089711

[置換基番号;R21,R27,R25]:[RT1;H,H,Me],[RT2;H,H,Et],[RT3;H,H,Pr],[RT4;H,H,i-Pr],[RT5;H,H,c-Pr],[RT6;H,H,Bu],[RT7;H,H,t-Bu],[RT8;H,H,c-PrCH2],[RT9;H,H,Ph],[RT10;H,H,Bn],[RT11;H,H,CF3],[RT12;H,H,CF3CH2],[RT13;H,H,CF3CF2],[RT14;H,H,CF2H],[RT15;H,H,CF2HCH2],[RT16;F,H,Me],[RT17;F,H,Et],[RT18;F,H,Pr],[RT19;F,H,i-Pr],[RT20;F,H,c-Pr],[RT21;F,H,Bu],[RT22;F,H,t-Bu],[RT23;F,H,c-PrCH2],[RT24;F,H,Ph],[RT25;F,H,Bn],[RT26;F,H,CF3],[RT27;F,H,CF3CH2],[RT28;F,H,CF3CF2],[RT29;F,H,CF2H],[RT30;F,H,CF2HCH2],[RT31;H,F,Me],[RT32;H,F,Et],[RT33;H,F,Pr],[RT34;H,F,i-Pr],[RT35;H,F,c-Pr],[RT36;H,F,Bu],[RT37;H,F,t-Bu],[RT38;H,F,c-PrCH2],[RT39;H,F,Ph],[RT40;H,F,Bn],[RT41;H,F,CF3],[RT42;H,F,CF3CH2],[RT43;H,F,CF3CF2],[RT44;H,F,CF2H],[RT45;H,F,CF2HCH2] [Substituent group number; R 21, R 27, R 25]: [RT1; H, H, Me], [RT2; H, H, Et], [RT3; H, H, Pr], [RT4; H, H, i-Pr], [RT5; H, H, c-Pr], [RT 6; H, H, Bu], [RT 7; H, H, t-Bu], [RT 8; H, H, c- PrCH 2], [RT9; H , H, Ph], [RT10; H, H, Bn], [RT11; H, H, CF 3], [RT12; H, H, CF 3 CH 2], [RT13 ; H, H, CF 3 CF 2], [RT14; H, H, CF 2 H], [RT15; H, H, CF 2 HCH 2], [RT16; F, H, Me], [RT17; F , H, Et], [RT 18; F, H, Pr], [RT 19; F, H, i-Pr], [RT 20; F, H, c-Pr], [RT 21; F, H, Bu], [RT 22; F, H, t-Bu], [RT 23; F, H, c-PrCH 2 ], [RT 24; F, H, Ph], [RT 25; F, H, Bn], [RT 26; H, CF 3 ], [RT 27; F, H, CF 3 CH 2 ], [RT 28; F, H, CF 3 CF 2 ], [RT 29; F, H, CF 2 H], [RT 30; F, H , CF 2 HCH 2 ], [RT 31; H, F, Me], [RT 32; H, F, Et], [RT 33; H, F, Pr], [RT 34; H, F, i-Pr], [RT RT 35; H, F, c-Pr], [RT 36; H, F, Bu], [RT 37; H, F, t-Bu], [RT 38; H, F, c-PrCH 2 ], [RT 39; H , F, Ph], [RT 40; H, F, Bn], [RT 41; H, F, CF 3 ], [RT 42; H, F, CF 3 CH 2 ], [RT 43; H, F, CF 3 CF 2 ], [RT 44; H, F, CF 2 H], [RT 45; H, F, CF 2 HCH 2 ]

式(XXII)

Figure 2019089711
〔式中、R25及びQ21は上記と同じ意味を表す。〕
で表される化合物において、Q21及びR25の組合わせが下記に示される置換基番号RU1〜RU30のいずれかに記載の組合わせである化合物(以下、置換基番号RU1〜RU30の化合物を本発明化合物RU1〜RU30と表し、本発明化合物RU1〜RU30をまとめて本発明化合物RUと表す)は、上記の製造法に記載の方法に準じて得ることができる。
なお、置換基番号RU1〜RU30とは、式(XXII)で表される化合物における、Q21及びR25の組合せを表すものであり、以下、[置換基番号;Q21,R25]と記す。
例えば、置換基番号RU4とは、Q21が酸素原子であり、R25がイソプロピル基である組合せを表す。 Formula (XXII)
Figure 2019089711
[Wherein, R 25 and Q 21 represent the same meaning as described above. ]
Wherein the combination of Q 21 and R 25 is a combination as set forth in any of Substituent Nos. RU 1 to RU 30 shown below (hereinafter referred to as “compound of Substituent No. RU 1 to RU 30” Inventive compounds RU1 to RU30, and the compounds RU1 to RU30 of the present invention are collectively referred to as the compound RU of the present invention) can be obtained according to the method described in the above production method.
In addition, the substituent numbers RU1 to RU30 represent a combination of Q 21 and R 25 in the compound represented by the formula (XXII), and hereinafter referred to as [substituent number: Q 21 , R 25 ] .
For example, the substituent number RU4 represents a combination in which Q 21 is an oxygen atom and R 25 is an isopropyl group.

例えば、本発明化合物RU4とは、式(XXII)で表される化合物において置換基番号がRU4である化合物を意味し、式(XXII)で表される化合物において、Q21が酸素原子であり、R25がイソプロピル基である下記化合物を表す。

Figure 2019089711
For example, the compound RU4 of the present invention means a compound represented by the formula (XXII) in which the substituent number is RU4, and in the compound represented by the formula (XXII), Q 21 is an oxygen atom, The following compounds in which R 25 is an isopropyl group are represented.
Figure 2019089711

[置換基番号;Q21,R25]:[RU1;O,Me],[RU2;O,Et],[RU3;O,Pr],[RU4;O,i-Pr],[RU5;O,c-Pr],[RU6;O,Bu],[RU7;O,t-Bu],[RU8;O,c-PrCH2],[RU9;O,Ph],[RU10;O,Bn],[RU11;O,CF3],[RU12;O,CF3CH2],[RU13;O,CF3CF2],[RU14;O,CF2H],[RU15;O,CF2HCH2],[RU16;NH,Me],[RU17;NH,Et],[RU18;NH,Pr],[RU19;NH,i-Pr],[RU20;NH,c-Pr],[RU21;NH,Bu],[RU22;NH,t-Bu],[RU23;NH,c-PrCH2],[RU24;NH,Ph],[RU25;NH,Bn],[RU26;NH,CF3],[RU27;NH,CF3CH2],[RU28;NH,CF3CF2],[RU29;NH,CF2H],[RU30;NH,CF2HCH2] [Substituent No. Q 21 , R 25 ]: [RU 1; O, Me], [RU 2; O, Et], [RU 3; O, Pr], [RU 4; O, i-Pr], [RU 5; , c-Pr], [RU6; O, Bu], [RU 7; O, t-Bu], [RU 8; O, c-PrCH 2 ], [RU 9; O, Ph], [RU 10; O, Bn] , [RU 11; O, CF 3 ], [RU 12; O, CF 3 CH 2 ], [RU 13; O, CF 3 CF 2 ], [RU 14; O, CF 2 H], [RU 15; O, CF 2 HCH 2 ], [RU16; NH, Me], [RU17; NH, Et], [RU18; NH, Pr], [RU19; NH, i-Pr], [RU20; NH, c-Pr], [RU21; NH, Bu], [RU 22; NH, t-Bu], [RU 23; NH, c-PrCH 2 ], [RU 24; NH, Ph], [RU 25; NH, Bn], [RU 26; NH, CF 3 ] , [RU 27; NH, CF 3 CH 2 ], [RU 28; NH, CF 3 CF 2 ], [RU 29; NH, CF 2 H], [RU 30; NH, CF 2 HCH 2 ]

式(XXIII)

Figure 2019089711
〔式中、R25及びQ21は上記と同じ意味を表す。〕
で表される化合物において、Q21及びR25の組合わせが下記に示される置換基番号RV1〜RV30のいずれかに記載の組合わせである化合物(以下、置換基番号RV1〜RV30の化合物を本発明化合物RV1〜RV30と表し、本発明化合物RV1〜RV30をまとめて本発明化合物RVと表す)は、上記の製造法に記載の方法に準じて得ることができる。
なお、置換基番号RV1〜RV30とは、式(XXIII)で表される化合物における、Q21及びR25の組合せを表すものであり、以下、[置換基番号;Q21,R25]と記す。
例えば、置換基番号RV4とは、Q21が酸素原子であり、R25がイソプロピル基である組合せを表す。 Formula (XXIII)
Figure 2019089711
[Wherein, R 25 and Q 21 represent the same meaning as described above. ]
Wherein the combination of Q 21 and R 25 is a combination as set forth in any one of Substituent Nos. RV 1 to RV 30 (hereinafter referred to as “compound of Substituent No. RV 1 to RV 30”) Invention compounds RV1 to RV30, and compounds of the invention RV1 to RV30 are collectively referred to as compound of the invention RV) can be obtained according to the method described in the above-mentioned production method.
Substituent numbers RV1 to RV30 each denote a combination of Q 21 and R 25 in the compound represented by formula (XXIII), and hereinafter, referred to as [substituent number: Q 21 , R 25 ] .
For example, the substituent number RV4 represents a combination in which Q 21 is an oxygen atom and R 25 is an isopropyl group.

例えば、本発明化合物RV4とは、式(XXIII)で表される化合物において置換基番号がRV4である化合物を意味し、式(XXIII)で表される化合物において、Q21が酸素原子であり、R25がイソプロピル基である下記化合物を表す。

Figure 2019089711
For example, the compound of the present invention RV4 means a compound represented by the formula (XXIII) in which the substituent number is RV4, and in the compound represented by the formula (XXIII), Q 21 is an oxygen atom, The following compounds in which R 25 is an isopropyl group are represented.
Figure 2019089711

[置換基番号;Q21,R25]:[RV1;O,Me],[RV2;O,Et],[RV3;O,Pr],[RV4;O,i-Pr],[RV5;O,c-Pr],[RV6;O,Bu],[RV7;O,t-Bu],[RV8;O,c-PrCH2],[RV9;O,Ph],[RV10;O,Bn],[RV11;O,CF3],[RV12;O,CF3CH2],[RV13;O,CF3CF2],[RV14;O,CF2H],[RV15;O,CF2HCH2],[RV16;NH,Me],[RV17;NH,Et],[RV18;NH,Pr],[RV19;NH,i-Pr],[RV20;NH,c-Pr],[RV21;NH,Bu],[RV22;NH,t-Bu],[RV23;NH,c-PrCH2],[RV24;NH,Ph],[RV25;NH,Bn],[RV26;NH,CF3],[RV27;NH,CF3CH2],[RV28;NH,CF3CF2],[RV29;NH,CF2H],[RV30;NH,CF2HCH2] [Substituent No. Q 21 , R 25 ]: [RV 1; O, Me], [RV 2; O, Et], [RV 3; O, Pr], [RV 4; O, i-Pr], [RV 5; , c-Pr], [RV 6; O, Bu], [RV 7; O, t-Bu], [RV 8; O, c-PrCH 2 ], [RV 9; O, Ph], [RV 10; O, Bn] , [RV11; O, CF 3 ], [RV12; O, CF 3 CH 2], [RV13; O, CF 3 CF 2], [RV14; O, CF 2 H], [RV15; O, CF 2 HCH 2 ], [RV16; NH, Me], [RV17; NH, Et], [RV18; NH, Pr], [RV19; NH, i-Pr], [RV20; NH, c-Pr], [RV21; NH, Bu], [RV 22; NH, t-Bu], [RV 23; NH, c-PrCH 2 ], [RV 24; NH, Ph], [RV 25; NH, Bn], [RV 26; NH, CF 3 ] , [RV27; NH, CF 3 CH 2], [RV28; NH, CF 3 CF 2], [RV29; NH, CF 2 H], [RV30; NH, CF 2 HCH 2]

式(XXIV)

Figure 2019089711
〔式中、R25及びQ21は上記と同じ意味を表す。〕
で表される化合物において、Q21及びR25の組合わせが下記に示される置換基番号RW1〜RW30のいずれかに記載の組合わせである化合物(以下、置換基番号RW1〜RW30の化合物を本発明化合物RW1〜RW30と表し、本発明化合物RW1〜RW30をまとめて本発明化合物RWと表す)は、上記の製造法に記載の方法に準じて得ることができる。
なお、置換基番号RW1〜RW30とは、式(XXIV)で表される化合物における、Q21及びR25の組合せを表すものであり、以下、[置換基番号;Q21,R25]と記す。
例えば、置換基番号RW4とは、Q21が酸素原子であり、R25がイソプロピル基である組合せを表す。 Formula (XXIV)
Figure 2019089711
[Wherein, R 25 and Q 21 represent the same meaning as described above. ]
Wherein the combination of Q 21 and R 25 is a combination according to any one of the substituent numbers RW 1 to RW 30 shown below (hereinafter referred to as a compound of substituent numbers RW 1 to RW 30 Invention compounds RW1 to RW30, and the compounds of the invention RW1 to RW30 are collectively referred to as the compound of the invention RW) can be obtained according to the method described in the above production method.
Substituent numbers RW1 to RW30 each represent a combination of Q 21 and R 25 in the compound represented by formula (XXIV), and hereinafter, referred to as [substituent number: Q 21 , R 25 ] .
For example, the substituent number RW4 represents a combination in which Q 21 is an oxygen atom and R 25 is an isopropyl group.

例えば、本発明化合物RW4とは、式(XXIV)で表される化合物において置換基番号がRW4である化合物を意味し、式(XXIV)で表される化合物において、Q21が酸素原子であり、R25がイソプロピル基である下記化合物を表す。

Figure 2019089711
For example, the compound RW4 of the present invention means a compound represented by the formula (XXIV) in which the substituent number is RW4, and in the compound represented by the formula (XXIV), Q 21 is an oxygen atom, The following compounds in which R 25 is an isopropyl group are represented.
Figure 2019089711

[置換基番号;Q21,R25]:[RW1;O,Me],[RW2;O,Et],[RW3;O,Pr],[RW4;O,i-Pr],[RW5;O,c-Pr],[RW6;O,Bu],[RW7;O,t-Bu],[RW8;O,c-PrCH2],[RW9;O,Ph],[RW10;O,Bn],[RW11;O,CF3],[RW12;O,CF3CH2],[RW13;O,CF3CF2],[RW14;O,CF2H],[RW15;O,CF2HCH2],[RW16;NH,Me],[RW17;NH,Et],[RW18;NH,Pr],[RW19;NH,i-Pr],[RW20;NH,c-Pr],[RW21;NH,Bu],[RW22;NH,t-Bu],[RW23;NH,c-PrCH2],[RW24;NH,Ph],[RW25;NH,Bn],[RW26;NH,CF3],[RW27;NH,CF3CH2],[RW28;NH,CF3CF2],[RW29;NH,CF2H],[RW30;NH,CF2HCH2] [Substituent No. Q 21 , R 25 ]: [RW 1; O, Me], [RW 2; O, Et], [RW 3; O, Pr], [RW 4; O, i-Pr], [RW 5; , c-Pr], [RW 6; O, Bu], [RW 7; O, t-Bu], [RW 8; O, c-PrCH 2 ], [RW 9; O, Ph], [RW 10; O, Bn] [RW 11; O, CF 3 ], [RW 12; O, CF 3 CH 2 ], [RW 13; O, CF 3 CF 2 ], [RW 14; O, CF 2 H], [RW 15; O, CF 2 HCH 2 ], [RW 16; NH, Me], [RW 17; NH, Et], [RW 18; NH, Pr], [RW 19; NH, i-Pr], [RW 20; NH, c-Pr], [RW 21; NH, Bu], [RW 22; NH, t-Bu], [RW 23; NH, c-PrCH 2 ], [RW 24; NH, Ph], [RW 25; NH, Bn], [RW 26; NH, CF 3 ] , [RW 27; NH, CF 3 CH 2 ], [RW 28; NH, CF 3 CF 2 ], [RW 29; NH, CF 2 H], [RW 30; NH, CF 2 HCH 2 ]

式(XXV)

Figure 2019089711
〔式中、R25及びQ21は上記と同じ意味を表す。〕
で表される化合物において、Q21及びR25の組合わせが下記に示される置換基番号RX1〜RX30のいずれかに記載の組合わせである化合物(以下、置換基番号RX1〜RX30の化合物を本発明化合物RX1〜RX30と表し、本発明化合物RX1〜RX30をまとめて本発明化合物RXと表す)は、上記の製造法に記載の方法に準じて得ることができる。
なお、置換基番号RX1〜RX30とは、式(XXV)で表される化合物における、Q21及びR25の組合せを表すものであり、以下、[置換基番号;Q21,R25]と記す。
例えば、置換基番号RX4とは、Q21が酸素原子であり、R25がイソプロピル基である組合せを表す。 Formula (XXV)
Figure 2019089711
[Wherein, R 25 and Q 21 represent the same meaning as described above. ]
Wherein the combination of Q 21 and R 25 is a combination as set forth in any one of Substituent Nos. RX 1 to RX 30 shown below (hereinafter referred to as “compound of Substituent No. RX 1 to RX 30” Inventive compounds RX1 to RX30, and the compounds of the present invention RX1 to RX30 are collectively referred to as the compound of the present invention RX) can be obtained according to the method described in the above-mentioned production method.
Substituent numbers RX1 to RX30 each represent a combination of Q 21 and R 25 in the compound represented by formula (XXV), and hereinafter referred to as [substituent number; Q 21 , R 25 ] .
For example, the substituent number RX4 represents a combination in which Q 21 is an oxygen atom and R 25 is an isopropyl group.

例えば、本発明化合物RX4とは、式(XXV)で表される化合物において置換基番号がRX4である化合物を意味し、式(XXV)で表される化合物において、Q21が酸素原子であり、R23がイソプロピル基である下記化合物を表す。

Figure 2019089711
For example, the compound of the present invention RX4 means a compound represented by the formula (XXV) in which the substituent number is RX4, and in the compound represented by the formula (XXV), Q 21 is an oxygen atom, It represents the following compound wherein R 23 is an isopropyl group.
Figure 2019089711

[置換基番号;Q21,R25]:[RX1;O,Me],[RX2;O,Et],[RX3;O,Pr],[RX4;O,i-Pr],[RX5;O,c-Pr],[RX6;O,Bu],[RX7;O,t-Bu],[RX8;O,c-PrCH2],[RX9;O,Ph],[RX10;O,Bn],[RX11;O,CF3],[RX12;O,CF3CH2],[RX13;O,CF3CF2],[RX14;O,CF2H],[RX15;O,CF2HCH2],[RX16;NH,Me],[RX17;NH,Et],[RX18;NH,Pr],[RX19;NH,i-Pr],[RX20;NH,c-Pr],[RX21;NH,Bu],[RX22;NH,t-Bu],[RX23;NH,c-PrCH2],[RX24;NH,Ph],[RX25;NH,Bn],[RX26;NH,CF3],[RX27;NH,CF3CH2],[RX28;NH,CF3CF2],[RX29;NH,CF2H],[RX30;NH,CF2HCH2] [Substituent No. Q 21 , R 25 ]: [RX1; O, Me], [RX2; O, Et], [RX3; O, Pr], [RX4; O, i-Pr], [RX5; , c-Pr], [RX6 ; O, Bu], [RX7; O, t-Bu], [RX8; O, c-PrCH 2], [RX9; O, Ph], [RX10; O, Bn] , [RX11; O, CF 3 ], [RX12; O, CF 3 CH 2], [RX13; O, CF 3 CF 2], [RX14; O, CF 2 H], [RX15; O, CF 2 HCH 2 ], [RX16; NH, Me], [RX17; NH, Et], [RX18; NH, Pr], [RX19; NH, i-Pr], [RX20; NH, c-Pr], [RX21; NH, Bu], [RX22; NH, t-Bu], [RX23; NH, c-PrCH 2], [RX24; NH, Ph], [RX25; NH, Bn], [RX26; NH, CF 3] , [RX27; NH, CF 3 CH 2], [RX28; NH, CF 3 CF 2], [RX29; NH, CF 2 H], [RX30; NH, CF 2 HCH 2]

式(XXVI)

Figure 2019089711
〔式中、R31、R32及びR33は上記と同じ意味を表す。〕
で表される化合物において、R31、R32及びR33の組合わせが下記に示される置換基番号RY1〜RY1550のいずれかに記載の組合わせである化合物(以下、置換基番号RY1〜RY1550の化合物を本発明化合物RY1〜RY1550と表し、本発明化合物RY1〜RY1550をまとめて本発明化合物RYと表す)は、上記の製造法に記載の方法に準じて得ることができる。
なお、置換基番号RY1〜RY1550とは、式(XXVI)で表される化合物における、R31、R32及びR33の組合せを表すものであり、以下、[置換基番号;R31,R32,R33]と記す。
例えば、置換基番号RY4とは、R31が水素原子であり、R32が水素原子であり、R33がイソプロピル基である組合せを表す。 Formula (XXVI)
Figure 2019089711
[Wherein, R 31 , R 32 and R 33 represent the same meaning as described above. ]
Wherein the combination of R 31 , R 32 and R 33 is a combination as set forth in any one of Substituent Nos. RY 1 to RY 15 50 shown below (hereinafter referred to as Substituent Nos. RY 1 to RY 1550) The compounds are represented by the compounds RY1 to RY1550 of the present invention, and the compounds RY1 to RY1550 of the present invention are collectively referred to as the compound RY of the present invention) can be obtained according to the method described in the above-mentioned production method.
Note that the substituent number RY1~RY1550, in the compound of formula (XXVI), and represents the combination of R 31, R 32 and R 33, below, Substituent group number; R 31, R 32 , R 33 ].
For example, the substituent number RY4 represents a combination in which R 31 is a hydrogen atom, R 32 is a hydrogen atom, and R 33 is an isopropyl group.

例えば、本発明化合物RY4とは、式(XXVI)で表される化合物において置換基番号がRX4である化合物を意味し、式(XXVI)で表される化合物において、R31が水素原子であり、R32が水素原子であり、R33がイソプロピル基である下記化合物を表す。

Figure 2019089711
For example, the compound of the present invention RY4 means a compound represented by the formula (XXVI) in which the substituent number is RX4, and in the compound represented by the formula (XXVI), R 31 is a hydrogen atom, R 32 represents a hydrogen atom, and R 33 represents an isopropyl group.
Figure 2019089711

[置換基番号;R31,R32,R33]:[RY1;H,H,Me],[RY2;H,H,Et],[RY3;H,H,Pr],[RY4;H,H,i-Pr],[RY5;H,H,c-Pr],[RY6;H,H,t-Bu],[RY7;H,H,Bu],[RY8;H,H,t-Bu],[RY9;H,H,c-PrCH2],[RY10;H,H,Ph],[RY11;H,H,Bn],[RY12;H,H,CF3],[RY13;H,H,CF3CH2],[RY14;H,H,CF3CF2],[RY15;H,H,CF2H],[RY16;H,H,CF2HCH2],[RY17;Me,H,Me],[RY18;Me,H,Et],[RY19;Me,H,Pr],[RY20;Me,H,i-Pr],[RY21;Me,H,c-Pr],[RY22;Me,H,t-Bu],[RY23;Me,H,Bu],[RY24;Me,H,t-Bu],[RY25;Me,H,c-PrCH2],[RY26;Me,H,Ph],[RY27;Me,H,Bn],[RY28;Me,H,CF3],[RY29;Me,H,CF3CH2],[RY30;Me,H,CF3CF2],[RY31;Me,H,CF2H],[RY32;Me,H,CF2HCH2],[RY33;Et,H,Me],[RY34;Et,H,Et],[RY35;Et,H,Pr],[RY36;Et,H,i-Pr],[RY37;Et,H,c-Pr],[RY38;Et,H,t-Bu],[RY39;Et,H,Bu],[RY40;Et,H,t-Bu],[RY41;Et,H,c-PrCH2],[RY42;Et,H,Ph],[RY43;Et,H,Bn],[RY44;Et,H,CF3],[RY45;Et,H,CF3CH2],[RY46;Et,H,CF3CF2],[RY47;Et,H,CF2H],[RY48;Et,H,CF2HCH2],[RY49;Pr,H,Me],[RY50;Pr,H,Et],[RY51;Pr,H,Pr],[RY52;Pr,H,i-Pr],[RY53;Pr,H,c-Pr],[RY54;Pr,H,t-Bu],[RY55;Pr,H,Bu],[RY56;Pr,H,t-Bu],[RY57;Pr,H,c-PrCH2],[RY58;Pr,H,Ph],[RY59;Pr,H,Bn],[RY60;Pr,H,CF3],[RY61;Pr,H,CF3CH2],[RY62;Pr,H,CF3CF2],[RY63;Pr,H,CF2H],[RY64;Pr,H,CF2HCH2],[RY65;i-Pr,H,Me],[RY66;i-Pr,H,Et],[RY67;i-Pr,H,Pr],[RY68;i-Pr,H,i-Pr],[RY69;i-Pr,H,c-Pr],[RY70;i-Pr,H,t-Bu],[RY71;i-Pr,H,Bu],[RY72;i-Pr,H,t-Bu],[RY73;i-Pr,H,c-PrCH2],[RY74;i-Pr,H,Ph],[RY75;i-Pr,H,Bn],[RY76;i-Pr,H,CF3],[RY77;i-Pr,H,CF3CH2],[RY78;i-Pr,H,CF3CF2],[RY79;i-Pr,H,CF2H],[RY80;i-Pr,H,CF2HCH2],[RY81;c-Pr,H,Me],[RY82;c-Pr,H,Et],[RY83;c-Pr,H,Pr],[RY84;c-Pr,H,i-Pr],[RY85;c-Pr,H,c-Pr],[RY86;c-Pr,H,t-Bu],[RY87;c-Pr,H,Bu],[RY88;c-Pr,H,t-Bu],[RY89;c-Pr,H,c-PrCH2],[RY90;c-Pr,H,Ph],[RY91;c-Pr,H,Bn],[RY92;c-Pr,H,CF3],[RY93;c-Pr,H,CF3CH2],[RY94;c-Pr,H,CF3CF2],[RY95;c-Pr,H,CF2H],[RY96;c-Pr,H,CF2HCH2],[RY97;c-PrCH2,H,Me],[RY98;c-PrCH2,H,Et],[RY99;c-PrCH2,H,Pr],[RY100;c-PrCH2,H,i-Pr],[RY101;c-PrCH2,H,c-Pr],[RY102;c-PrCH2,H,t-Bu],[RY103;c-PrCH2,H,Bu],[RY104;c-PrCH2,H,t-Bu],[RY105;c-PrCH2,H,c-PrCH2],[RY106;c-PrCH2,H,Ph],[RY107;c-PrCH2,H,Bn],[RY108;c-PrCH2,H,CF3],[RY109;c-PrCH2,H,CF3CH2],[RY110;c-PrCH2,H,CF3CF2],[RY111;c-PrCH2,H,CF2H],[RY112;c-PrCH2,H,CF2HCH2],[RY113;i-Bu,H,Me],[RY114;i-Bu,H,Et],[RY115;i-Bu,H,Pr],[RY116;i-Bu,H,i-Pr],[RY117;i-Bu,H,c-Pr],[RY118;i-Bu,H,t-Bu],[RY119;i-Bu,H,Bu],[RY120;i-Bu,H,t-Bu],[RY121;i-Bu,H,c-PrCH2],[RY122;i-Bu,H,Ph],[RY123;i-Bu,H,Bn],[RY124;i-Bu,H,CF3],[RY125;i-Bu,H,CF3CH2],[RY126;i-Bu,H,CF3CF2],[RY127;i-Bu,H,CF2H],[RY128;i-Bu,H,CF2HCH2],[RY129;CF3CH2,H,Me],[RY130;CF3CH2,H,Et],[RY131;CF3CH2,H,Pr],[RY132;CF3CH2,H,i-Pr],[RY133;CF3CH2,H,c-Pr],[RY134;CF3CH2,H,t-Bu],[RY135;CF3CH2,H,Bu],[RY136;CF3CH2,H,t-Bu],[RY137;CF3CH2,H,c-PrCH2],[RY138;CF3CH2,H,Ph],[RY139;CF3CH2,H,Bn],[RY140;CF3CH2,H,CF3],[RY141;CF3CH2,H,CF3CH2],[RY142;CF3CH2,H,CF3CF2],[RY143;CF3CH2,H,CF2H],[RY144;CF3CH2,H,CF2HCH2],[RY145;CF2HCH2,Me,Me],[RY146;CF2HCH2,H,Et],[RY147;CF2HCH2,H,Pr],[RY148;CF2HCH2,H,i-Pr],[RY149;CF2HCH2,H,c-Pr],[RY150;CF2HCH2,H,t-Bu],[RY151;CF2HCH2,H,Bu],[RY152;CF2HCH2,H,t-Bu],[RY153;CF2HCH2,H,c-PrCH2],[RY154;CF2HCH2,H,Ph],[RY155;CF2HCH2,H,Bn],[RY156;CF2HCH2,H,CF3],[RY157;CF2HCH2,H,CF3CH2],[RY158;CF2HCH2,H,CF3CF2],[RY159;CF2HCH2,H,CF2H],[RY160;CF2HCH2,H,CF2HCH2],[RY161;MeOCH2,H,Me],[RY162;MeOCH2,H,Et],[RY163;MeOCH2,H,Pr],[RY164;MeOCH2,H,i-Pr],[RY165;MeOCH2,H,c-Pr],[RY166;MeOCH2,H,t-Bu],[RY167;MeOCH2,H,Bu],[RY168;MeOCH2,H,t-Bu],[RY169;MeOCH2,H,c-PrCH2],[RY170;MeOCH2,H,Ph],[RY171;MeOCH2,H,Bn],[RY172;MeOCH2,H,CF3],[RY173;MeOCH2,H,CF3CH2],[RY174;MeOCH2,H,CF3CF2],[RY175;MeOCH2,H,CF2H],[RY176;MeOCH2,H,CF2HCH2],[RY177;EtOCH2,H,Me],[RY178;EtOCH2,H,Et],[RY179;EtOCH2,H,Pr],[RY180;EtOCH2,H,i-Pr],[RY181;EtOCH2,H,c-Pr],[RY182;EtOCH2,H,t-Bu],[RY183;EtOCH2,H,Bu],[RY184;EtOCH2,H,t-Bu],[RY185;EtOCH2,H,c-PrCH2],[RY186;EtOCH2,H,Ph],[RY187;EtOCH2,H,Bn],[RY188;EtOCH2,H,CF3],[RY189;EtOCH2,H,CF3CH2],[RY190;EtOCH2,H,CF3CF2],[RY191;EtOCH2,H,CF2H],[RY192;EtOCH2,H,CF2HCH2],[RY193;MeSCH2,H,Me],[RY194;MeSCH2,H,Et],[RY195;MeSCH2,H,Pr],[RY196;MeSCH2,H,i-Pr],[RY197;MeSCH2,H,c-Pr],[RY198;MeSCH2,H,t-Bu],[RY199;MeSCH2,H,Bu],[RY200;MeSCH2,H,t-Bu], [Substituent number; R 31 , R 32 , R 33 ]: [RY 1; H, H, Me], [RY 2; H, H, Et], [RY 3; H, H, Pr], [RY 4; H, H, i-Pr], [RY5; H, H, c-Pr], [RY 6; H, H, t-Bu], [RY 7; H, H, Bu], [RY 8; H, H, t- Bu], [RY9; H, H, c-PrCH 2], [RY10; H, H, Ph], [RY11; H, H, Bn], [RY12; H, H, CF 3], [RY13; H, H, CF 3 CH 2 ], [RY 14; H, H, CF 3 CF 2 ], [RY 15; H, H, CF 2 H], [RY 16; H, H, CF 2 HCH 2 ], [RY 17 Me, H, Me], [RY 18; Me, H, Et], [RY 19; Me, H, Pr], [RY 20; Me, H, i-Pr], [RY 21; Me, H, c-Pr ], [RY 22; Me, H, t-Bu], [RY 23; Me, H, Bu], [RY 24; Me, H, t-Bu], [RY 25; Me, H, c-PrCH 2 ], [ RY26; Me, H, Ph] , [RY27; Me, H, Bn], [RY28; Me, H, CF 3], [RY29; Me, H, CF 3 CH 2], [RY30; Me, H, CF 3 CF 2 ], [RY 31; Me, H, CF 2 H], [RY 32; Me, H, CF 2 HCH 2 ], [RY 33; Et, H, Me], [RY 34; Et, H, Et] , [RY 35; Et, H, Pr], [RY 36; Et, H, i-Pr], [RY 37; Et, H, c-Pr], [RY 38; Et, H, t-Bu], [RY 39; Et, H, Bu], [ RY40; Et, H, t-Bu], [RY41; Et, H, c-PrCH 2], [RY42; Et, H, Ph], [RY43; Et, H, Bn ], [RY 44; Et, H, CF 3 ], [RY 45; Et, H, CF 3 CH 2 ], [RY 46; Et, H, CF 3 CF 2 ], [RY 47; Et, H, CF 2 H] , [RY 48; Et, H, CF 2 HCH 2 ], [RY 49; Pr, H, Me], [RY 50; Pr, H, Et], [RY 51; Pr, H, Pr], [RY 52; Pr, H , i-Pr], [RY 53; Pr, H, c-Pr], [RY 54; Pr, H, t-Bu], [RY 55; Pr, H, Bu], [RY 56; Pr, H, t-Bu ], [RY 57; Pr, H, c-PrCH 2 ], [RY 58; Pr, H, Ph], [RY 59; Pr, H, Bn], [RY 60; Pr, H, CF 3 ], [RY 61; Pr, H , CF 3 CH 2 ], [RY 62; Pr, H, CF 3 CF 2 ], [RY 63; Pr, H, CF 2 H], [RY 64; Pr, H, CF 2 HCH 2 ], [RY 65; Pr, H, Me], [RY 66; i-Pr, H, Et], [RY 67; i-Pr, H, Pr], [RY 68; i-Pr, H, i-Pr], [RY 69; Pr, H, c-Pr], [RY 70; i-Pr, H, t-Bu], [RY 71; i-Pr, H, Bu], [RY 72; i-Pr, H, t-Bu], [RY 72; RY 73; i-Pr, H, c-PrCH 2 ], [RY 74; i-Pr, H, Ph], [RY 75; i-Pr, H, Bn], [RY 76; i-Pr, H, CF 3 ] , [RY 77; i-Pr, H, CF 3 CH 2 ], [RY 78; i-Pr, H, CF 3 CF 2 ], [RY 79; i-Pr, H, CF 2 H], [RY 80; Pr, H, CF 2 HCH 2 ], [RY81; c-Pr, H, Me], [RY82; c-Pr, H, Et], [RY83; c-Pr, H, Pr], [RY84; c -Pr, H, i-Pr], [RY 85; c-Pr, H, c-Pr], [RY 86; c-Pr, H, t-Bu], [RY 87; c-Pr, H, Bu], [RY88; c-Pr, H , t-Bu], [RY89; c-Pr, H, c-PrCH 2], [RY90; c-Pr, H, Ph], [RY91; c-Pr, H, Bn], [RY 92; c-Pr, H, CF 3 ], [RY 93; c-Pr, H, CF 3 CH 2 ], [RY 94; c-Pr, H, CF 3 CF 2 ], [RY 95; c -Pr, H, CF 2 H] , [RY96; c-Pr, H, CF 2 HCH 2], [RY97; c-PrCH 2, H, Me], [RY98; c-PrCH 2, H, Et] , [RY99; c-PrCH 2 , H, Pr], [RY100; c-PrCH 2, H, i-Pr], [RY101; c-PrCH 2, H, c-Pr], [RY102; c-PrCH 2, H, t-Bu] , [RY103; c-PrCH 2, H, Bu], [RY104; c-PrCH 2, H, t-Bu], [RY105; c-PrCH 2, H, c-PrCH 2 ], [RY106; c-PrCH 2, H, Ph], [RY107; c-PrCH 2, H, Bn], [RY108; c-PrCH 2, H, CF 3], [RY109; c-PrCH 2, H, CF 3 CH 2], [RY110; c-PrCH 2, H, CF 3 CF 2], [RY111; c-PrCH 2, H, CF 2 H], [RY112; c-PrCH 2, H, CF 2 HCH 2], [RY113; i-Bu, H, Me], [RY114; i-Bu, H, Et], [RY115; i-Bu, H, Pr], [ RY116; i-Bu, H, i-Pr], [RY117; i-Bu, H, c-Pr], [RY 118; i-Bu, H, t-Bu], [RY119; i-Bu, H, Bu], [RY 120; i-Bu, H, t-Bu], [RY 121; i-Bu, H, c-PrCH 2 ], [RY 122; i-Bu, H, Ph], [RY 123; i-Bu , H, Bn], [RY 124; i-Bu, H, CF 3 ], [RY 125; i-Bu, H, CF 3 CH 2 ], [RY 126; i-Bu, H, CF 3 CF 2 ], [[ RY 127; i-Bu, H, CF 2 H], [RY 128; i-Bu, H, CF 2 HCH 2 ], [RY 129; CF 3 CH 2 , H, Me], [RY 130; CF 3 CH 2 , H , Et], [RY131; CF 3 CH 2 , H, Pr], [RY 132; CF 3 CH 2 , H, i-Pr], [RY 133; CF 3 CH 2 , H, c-Pr], [RY 134; CF 3 CH 2 , H, t-Bu], [RY 135; CF 3 CH 2 , H, Bu], [RY 136; CF 3 CH 2 , H, t-Bu], [RY 137; CF 3 CH 2 , H, c-PrCH 2], [RY138 ; CF 3 CH 2, H, Ph], [RY139; CF 3 CH 2, H, Bn], [RY140; CF 3 CH 2, H, CF 3], [RY141; CF 3 CH 2 , H, CF 3 CH 2 ], [RY 142; CF 3 CH 2 , H, CF 3 CF 2 ], [RY 143; CF 3 CH 2 , H, CF 2 H], [RY 144; CF 3 CH 2 , H, CF 2 HCH 2 ], [RY 145; CF 2 HCH 2 , Me, Me] , [RY146; CF 2 HCH 2 , H, Et], [RY147; CF 2 HCH 2, H, Pr], [RY148; CF 2 HCH 2, H, i-Pr], [RY149; CF 2 HCH 2, H, c-Pr], [ RY150; CF 2 HCH 2, H, t-Bu], [RY151; CF 2 HCH 2, H, Bu], [RY152; CF 2 HCH 2, H, t-Bu], [RY153; CF 2 HCH 2, H, c-PrCH 2], [RY154; CF 2 HCH 2, H, Ph], [RY155; CF 2 HCH 2, H, Bn], [RY156; CF 2 HCH 2, H, CF 3], [RY157 ; CF 2 HCH 2, H, CF 3 CH 2], [RY158; CF 2 HCH 2, H, CF 3 CF 2], [RY159; CF 2 HCH 2, H, CF 2 H], [RY160; CF 2 HCH 2, H, CF 2 HCH 2], [RY161; MeOCH 2, H, Me], [RY162; MeOCH 2, H, Et], [RY163; MeOCH 2, H, Pr ], [RY164; MeOCH 2, H, i-Pr], [RY165; MeOCH 2, H, c-Pr], [RY166; MeOCH 2, H, t-Bu], [RY167; MeOCH 2, H, Bu ], [RY168; MeOCH 2, H, t-Bu], [RY169; MeOCH 2, H, c-PrCH 2], [RY170; MeOCH 2, H, Ph], [RY171; MeOCH 2, H, Bn] , [RY172; MeOCH 2 , H, CF 3 ], [RY 173; MeOCH 2 , H, CF 3 CH 2 ], [RY 174; MeOCH 2 , H, CF 3 CF 2 ], [RY 175; MeOCH 2 , H, CF 2 H], [RY 176; MeOCH 2 , H, CF 2 HCH 2 ], [RY 177; EtOCH 2 , H, Me], [RY 178; EtOCH 2 , H, Et], [RY 179; EtOCH 2 , H, Pr] , [RY180; EtOCH 2 , H, i-Pr], [RY 181; EtOCH 2 , H, c-Pr], [RY 182; EtOCH 2 , H, t-Bu], [RY 183; EtOCH 2 , H, Bu] , [RY 184; EtOCH 2 , H, t-Bu], [RY 185; EtOCH 2 , H, c-PrCH 2 ], [RY 186; EtOCH 2 , H, Ph], [RY 187; EtOCH 2 , H, Bn], [RY 188; EtOCH 2 , H, CF 3 ], [RY 189; EtOCH 2 , H, CF 3 CH 2 ], [RY 190; EtOCH 2 , H, CF 3 CF 2 ], [RY 191; EtOCH 2 , H, CF 2 H], [RY 192; EtOCH 2 , H, CF 2 HCH 2], [RY193; MeSCH 2, H, Me], [RY194; MeSCH 2, H, Et], [RY195; MeSCH 2, H, Pr], [RY196; MeSCH 2, H, i -Pr], [RY 197; MeSCH 2 , H, c-Pr], [RY 198; MeSCH 2 , H, t-Bu], [RY 199; MeSCH 2 , H, Bu], [RY 200 ; MeSCH 2 , H, t -Bu],

[RY201;MeSCH2,H,c-PrCH2],[RY202;MeSCH2,H,Ph],[RY203;MeSCH2,H,Bn],[RY204;MeSCH2,H,CF3],[RY205;MeSCH2,H,CF3CH2],[RY206;MeSCH2,H,CF3CF2],[RY207;MeSCH2,H,CF2H],[RY208;MeSCH2,H,CF2HCH2],[RY209;EtSCH2,H,Me],[RY210;EtSCH2,H,Et],[RY211;EtSCH2,H,Pr],[RY212;EtSCH2,H,i-Pr],[RY213;EtSCH2,H,c-Pr],[RY214;EtSCH2,H,t-Bu],[RY215;EtSCH2,H,Bu],[RY216;EtSCH2,H,t-Bu],[RY217;EtSCH2,H,c-PrCH2],[RY218;EtSCH2,H,Ph],[RY219;EtSCH2,H,Bn],[RY220;EtSCH2,H,CF3],[RY221;EtSCH2,H,CF3CH2],[RY222;EtSCH2,H,CF3CF2],[RY223;EtSCH2,H,CF2H],[RY224;EtSCH2,H,CF2HCH2],[RY225;Ph,H,Me],[RY226;Ph,H,Et],[RY227;Ph,H,Pr],[RY228;Ph,H,i-Pr],[RY229;Ph,H,c-Pr],[RY230;Ph,H,t-Bu],[RY231;Ph,H,Bu],[RY232;Ph,H,t-Bu],[RY233;Ph,H,c-PrCH2],[RY234;Ph,H,Ph],[RY235;Ph,H,Bn],[RY236;Ph,H,CF3],[RY237;Ph,H,CF3CH2],[RY238;Ph,H,CF3CF2],[RY239;Ph,H,CF2H],[RY240;Ph,H,CF2HCH2],[RY241;Bn,H,Me],[RY242;Bn,H,Et],[RY243;Bn,H,Pr],[RY244;Bn,H,i-Pr],[RY245;Bn,H,c-Pr],[RY246;Bn,H,t-Bu],[RY247;Bn,H,Bu],[RY248;Bn,H,t-Bu],[RY249;Bn,H,c-PrCH2],[RY250;Bn,H,Ph],[RY251;Bn,H,Bn],[RY252;Bn,H,CF3],[RY253;Bn,H,CF3CH2],[RY254;Bn,H,CF3CF2],[RY255;Bn,H,CF2H],[RY256;Bn,H,CF2HCH2],[RY257;HCCCH2,H,Me],[RY258;HCCCH2,H,Et],[RY259;HCCCH2,H,Pr],[RY260;HCCCH2,H,i-Pr],[RY261;HCCCH2,H,c-Pr],[RY262;HCCCH2,H,t-Bu],[RY263;HCCCH2,H,Bu],[RY264;HCCCH2,H,t-Bu],[RY265;HCCCH2,H,c-PrCH2],[RY266;HCCCH2,H,Ph],[RY267;HCCCH2,H,Bn],[RY268;HCCCH2,H,CF3],[RY269;HCCCH2,H,CF3CH2],[RY270;HCCCH2,H,CF3CF2],[RY271;HCCCH2,H,CF2H],[RY272;HCCCH2,H,CF2HCH2],[RY273;CH3CCCH2,H,Me],[RY274;CH3CCCH2,H,Et],[RY275;CH3CCCH2,H,Pr],[RY276;CH3CCCH2,H,i-Pr],[RY277;CH3CCCH2,H,c-Pr],[RY278;CH3CCCH2,H,t-Bu],[RY279;CH3CCCH2,H,Bu],[RY280;CH3CCCH2,H,t-Bu],[RY281;CH3CCCH2,H,c-PrCH2],[RY282;CH3CCCH2,H,Ph],[RY283;CH3CCCH2,H,Bn],[RY284;CH3CCCH2,H,CF3],[RY285;CH3CCCH2,H,CF3CH2],[RY286;CH3CCCH2,H,CF3CF2],[RY287;CH3CCCH2,H,CF2H],[RY288;CH3CCCH2,H,CF2HCH2],[RY289;H,Me,Me],[RY290;H,Me,Et],[RY291;H,Me,Pr],[RY292;H,Me,i-Pr],[RY293;H,Me,c-Pr],[RY294;H,Me,t-Bu],[RY295;H,Me,Bu],[RY296;H,Me,t-Bu],[RY297;H,Me,c-PrCH2],[RY298;H,Me,Ph],[RY299;H,Me,Bn],[RY300;H,Me,CF3],[RY301;H,Me,CF3CH2],[RY302;H,Me,CF3CF2],[RY303;H,Me,CF2H],[RY304;H,Me,CF2HCH2],[RY305;Me,Me,Me],[RY306;Me,Me,Et],[RY307;Me,Me,Pr],[RY308;Me,Me,i-Pr],[RY309;Me,Me,c-Pr],[RY310;Me,Me,t-Bu],[RY311;Me,Me,Bu],[RY312;Me,Me,t-Bu],[RY313;Me,Me,c-PrCH2],[RY314;Me,Me,Ph],[RY315;Me,Me,Bn],[RY316;Me,Me,CF3],[RY317;Me,Me,CF3CH2],[RY318;Me,Me,CF3CF2],[RY319;Me,Me,CF2H],[RY320;Me,Me,CF2HCH2],[RY321;Et,Me,Me],[RY322;Et,Me,Et],[RY323;Et,Me,Pr],[RY324;Et,Me,i-Pr],[RY325;Et,Me,c-Pr],[RY326;Et,Me,t-Bu],[RY327;Et,Me,Bu],[RY328;Et,Me,t-Bu],[RY329;Et,Me,c-PrCH2],[RY330;Et,Me,Ph],[RY331;Et,Me,Bn],[RY332;Et,Me,CF3],[RY333;Et,Me,CF3CH2],[RY334;Et,Me,CF3CF2],[RY335;Et,Me,CF2H],[RY336;Et,Me,CF2HCH2],[RY337;Pr,Me,Me],[RY338;Pr,Me,Et],[RY339;Pr,Me,Pr],[RY340;Pr,Me,i-Pr],[RY341;Pr,Me,c-Pr],[RY342;Pr,Me,t-Bu],[RY343;Pr,Me,Bu],[RY344;Pr,Me,t-Bu],[RY345;Pr,Me,c-PrCH2],[RY346;Pr,Me,Ph],[RY347;Pr,Me,Bn],[RY348;Pr,Me,CF3],[RY349;Pr,Me,CF3CH2],[RY350;Pr,Me,CF3CF2],[RY351;Pr,Me,CF2H],[RY352;Pr,Me,CF2HCH2],[RY353;i-Pr,Me,Me],[RY354;i-Pr,Me,Et],[RY355;i-Pr,Me,Pr],[RY356;i-Pr,Me,i-Pr],[RY357;i-Pr,Me,c-Pr],[RY358;i-Pr,Me,t-Bu],[RY359;i-Pr,Me,Bu],[RY360;i-Pr,Me,t-Bu],[RY361;i-Pr,Me,c-PrCH2],[RY362;i-Pr,Me,Ph],[RY363;i-Pr,Me,Bn],[RY364;i-Pr,Me,CF3],[RY365;i-Pr,Me,CF3CH2],[RY366;i-Pr,Me,CF3CF2],[RY367;i-Pr,Me,CF2H],[RY368;i-Pr,Me,CF2HCH2],[RY369;c-Pr,Me,Me],[RY370;c-Pr,Me,Et],[RY371;c-Pr,Me,Pr],[RY372;c-Pr,Me,i-Pr],[RY373;c-Pr,Me,c-Pr],[RY374;c-Pr,Me,t-Bu],[RY375;c-Pr,Me,Bu],[RY376;c-Pr,Me,t-Bu],[RY377;c-Pr,Me,c-PrCH2],[RY378;c-Pr,Me,Ph],[RY379;c-Pr,Me,Bn],[RY380;c-Pr,Me,CF3],[RY381;c-Pr,Me,CF3CH2],[RY382;c-Pr,Me,CF3CF2],[RY383;c-Pr,Me,CF2H],[RY384;c-Pr,Me,CF2HCH2],[RY385;c-PrCH2,Me,Me],[RY386;c-PrCH2,Me,Et],[RY387;c-PrCH2,Me,Pr],[RY388;c-PrCH2,Me,i-Pr],[RY389;c-PrCH2,Me,c-Pr],[RY390;c-PrCH2,Me,t-Bu],[RY391;c-PrCH2,Me,Bu],[RY392;c-PrCH2,Me,t-Bu],[RY393;c-PrCH2,Me,c-PrCH2],[RY394;c-PrCH2,Me,Ph],[RY395;c-PrCH2,Me,Bn],[RY396;c-PrCH2,Me,CF3],[RY397;c-PrCH2,Me,CF3CH2],[RY398;c-PrCH2,Me,CF3CF2],[RY399;c-PrCH2,Me,CF2H],[RY400;c-PrCH2,Me,CF2HCH2], [RY201; MeSCH 2, H, c-PrCH 2], [RY202; MeSCH 2, H, Ph], [RY203; MeSCH 2, H, Bn], [RY204; MeSCH 2, H, CF 3], [RY205 ; MeSCH 2, H, CF 3 CH 2], [RY206; MeSCH 2, H, CF 3 CF 2], [RY207; MeSCH 2, H, CF 2 H], [RY208; MeSCH 2, H, CF 2 HCH 2 ], [RY 209; EtSCH 2 , H, Me], [RY 210; EtSCH 2 , H, Et], [RY 211; EtSCH 2 , H, Pr], [RY 212; EtSCH 2 , H, i-Pr], [ RY 213; EtSCH 2 , H, c-Pr], [RY 214; EtSCH 2 , H, t-Bu], [RY 215; EtSCH 2 , H, Bu], [RY 216; EtSCH 2 , H, t-Bu], [RY 216; RY217; EtSCH 2, H, c -PrCH 2], [RY218; EtSCH 2, H, Ph], [RY219; EtSCH 2, H, Bn], [RY220; EtSCH 2, H, CF 3], [RY221; EtSCH 2 , H, CF 3 CH 2 ], [RY222; EtSCH 2 , H, CF 3 CF 2 ], [RY 223; EtSCH 2 , H, CF 2 H], [RY 224; EtSCH 2 , H, CF 2 HCH 2 ], [RY 225; Ph, H, Me], [RY 226; Ph, H, Et], [RY 227; Ph, H, Pr], [RY 228; Ph, H, i-Pr], [RY 229; Ph, H , c-Pr], [RY 230; Ph, H, t-Bu], [RY 231; Ph, H, Bu], [RY 232; Ph, H, t-Bu], [RY 233; Ph, H, c-PrCH 2 ], [RY 234; Ph, H, Ph], [RY 235; Ph, H, Bn], [RY 236; Ph, H, CF 3 ], [RY 237; Ph, H, CF 3 CH 2 ], [RY 238; Ph, H, CF 3 CF 2 ], [RY239; Ph, H, CF 2 H], [RY240; Ph, H, CF 2 HCH 2], [RY241; Bn, H, Me], [RY242; Bn, H, Et], [RY 243; Bn, H, Pr], [RY 244; Bn, H, i-Pr], [RY 245; Bn, H, c-Pr] , [RY 246; Bn, H, t-Bu], [RY 247; Bn, H, Bu], [RY 248; Bn, H, t-Bu], [RY 249; Bn, H, c-PrCH 2 ], [RY 250] Bn, H, Ph], [RY 251; Bn, H, Bn], [RY 252; Bn, H, CF 3 ], [RY 253; Bn, H, CF 3 CH 2 ], [RY 254; Bn, H, CF 3 CF 2], [RY255; Bn, H, CF 2 H], [RY256; Bn, H, CF 2 HCH 2], [RY257; HCCCH 2, H, Me], [RY258; HCCCH 2, H, Et ], [RY259; HCCCH 2, H, Pr], [RY260; HCCCH 2, H, i-Pr], [RY261; HCCCH 2, H, c-Pr], [RY262; HCCCH 2, H, t-Bu ], [RY263; HCCCH 2, H, Bu], [RY264; HCCCH 2, H, t-Bu], [RY265; HCCCH 2, H, c-PrCH 2], [RY266; HCCCH 2, H, Ph] , [RY267; HCCCH 2, H , Bn], [RY268; HCCCH 2, H, CF 3], [RY269; HCCCH 2, H, CF 3 CH 2], [RY270; HCCCH 2, H, CF 3 CF 2 , [RY 271; HCCCH 2 , H, CF 2 H], [RY 272; HCCCH 2 , H, CF 2 HCH 2 ], [RY 273; CH 3 CCCH 2 , H, Me], [RY 274; CH 3 CCCH 2 , H, Et], [RY275; CH 3 CCCH 2, H, Pr], [RY276; CH 3 CCCH 2, H, i-Pr], [RY277; CH 3 CCCH 2, H, c-Pr], [RY278 ; CH 3 CCCH 2, H, t-Bu], [RY279; CH 3 CCCH 2, H, Bu], [RY280; CH 3 CCCH 2, H, t-Bu], [RY281; CH 3 CCCH 2, H , c-PrCH 2], [ RY282; CH 3 CCCH 2, H, Ph], [RY283; CH 3 CCCH 2, H, Bn], [RY284; CH 3 CCCH 2, H, CF 3], [RY285; CH 3 CCCH 2 , H, CF 3 CH 2 ], [RY 286; CH 3 CCCH 2, H, CF 3 CF 2 ], [RY287; CH 3 CCCH 2, H, CF 2 H], [RY288; CH 3 CCCH 2, H, CF 2 HCH 2], [RY289; H, Me, Me] , [RY 290; H, Me, Et], [RY 291; H, Me, Pr], [RY 292; H, Me, i-Pr], [RY 293; H, Me, c-Pr], [RY 294; H, Me, t-Bu], [RY 295; H, Me, Bu], [RY 296; H, Me, t-Bu], [RY 297; H, Me, c-PrCH 2 ], [RY 298; H, Me, Ph ], [RY 299; H, Me, Bn], [RY 300; H, Me, CF 3 ], [RY 301; H, Me, CF 3 CH 2 ], [RY 302; H, Me, CF 3 CF 2 ], [RY RY303; H, Me, CF 2 H], [RY304; H, Me, CF 2 HCH 2], [RY305; Me, Me, Me], [RY306; Me, Me, Et], [RY307; Me, Me , Pr], [RY 308; Me, Me, i-Pr], [RY 309; Me, Me, c-Pr], [RY 310; Me, Me, t-Bu], [RY 311; Me, Me, Bu], [RY312; Me, Me, t -Bu], [RY313; Me, Me, c-PrCH 2], [RY314; Me, Me, Ph], [RY315; Me, Me, Bn], [RY316; Me, Me, CF 3], [RY317 ; Me, Me, CF 3 CH 2], [RY318; Me, Me, CF 3 CF 2], [RY319; Me, Me, CF 2 H], [RY320; Me, Me , CF 2 HCH 2 ], [RY 321; Et, Me, Me], [RY 322; Et, Me, Et], [RY 323; Et, Me, Pr], [RY 324; Et, Me, i-Pr], [, RY 325; Et, Me, c-Pr], [RY 326; Et, Me, t-Bu], [RY 327; Et, Me, Bu], [RY 328; Et, Me, t-Bu], [RY 329; Et, Me, c-PrCH 2], [RY330; Et, Me, Ph], [RY331; Et, Me, Bn], [RY332; Et, Me, CF 3], [RY333; Et, Me, CF 3 CH 2 ], [RY 334; Et, Me, CF 3 CF 2 ], [RY 335; Et, Me, CF 2 H], [RY 336; Et, Me, CF 2 HCH 2 ], [RY 337; Pr, Me, Me], [RY 338; Pr, Me, Et], [RY 339; Pr, Me, Pr], [RY 340; Pr, Me, i -Pr], [RY 341; Pr, Me, c-Pr], [RY 342; Pr, Me, t-Bu], [RY 343; Pr, Me, Bu], [RY 344; Pr, Me, t-Bu], [RY345; Pr, Me, c -PrCH 2], [RY346; Pr, Me, Ph], [RY347; Pr, Me, Bn], [RY348; Pr, Me, CF 3], [RY349; Pr, Me , CF 3 CH 2 ], [RY 350; Pr, Me, CF 3 CF 2 ], [RY 351; Pr, Me, CF 2 H], [RY 352; Pr, Me, CF 2 HCH 2 ], [RY 353; Pr, Me, Me], [RY 354; i-Pr, Me, Et], [RY 355; i-Pr, Me, Pr], [RY 356; i-Pr, Me, i-Pr], [RY 357; Pr, Me, c-Pr], [RY 358; i-Pr, Me, t-Bu], [RY 359; i-Pr, Me, Bu], [RY 360; i-Pr, Me, t-Bu], [ RY361; i-Pr, Me, c-PrCH 2], [RY362; i-Pr, Me, Ph], [RY363; i-Pr, Me, Bn], [RY364; i-Pr, Me, CF 3] , [RY365; i-Pr, Me, CF 3 CH 2], [RY366; i-Pr, Me, CF 3 CF 2], [RY367; i-Pr, Me, CF 2 H], [RY368; i- Pr, Me, CF 2 HCH 2 ], [RY369; c-Pr, Me, Me], [RY370; c-Pr, Me, Et], [RY371; c-Pr, Me, Pr], [RY372; c -Pr, Me, i-Pr], [RY 373; c-Pr, Me, c-Pr], [RY 374; c-Pr, Me, t-Bu], [RY 375; c-Pr, Me, Bu], [RY376; c-Pr, Me , t-Bu], [RY377; c-Pr, Me, c-PrCH 2], [RY378; c-Pr, Me, Ph], [RY379; c-Pr, Me, Bn], [RY 380; c-Pr, Me, CF 3 ], [RY 381; c-Pr, Me, CF 3 CH 2 ], [RY 382; c-Pr, Me, CF 3 CF 2 ], [RY 383; c-Pr, Me, CF 2 H], [RY384; c-Pr, Me, CF 2 HCH 2], [RY385; c-PrCH 2, Me, Me], [RY386; c-PrCH 2, Me, Et ], [RY387; c-PrCH 2, Me, Pr], [RY388; c-PrCH 2, Me, i-Pr], [RY389; c-PrCH 2, Me, c-Pr], [RY390; c- PrCH 2, Me, t-Bu ], [RY391; c-PrCH 2, Me, Bu], [RY392; c-PrCH 2, Me, t-Bu], [RY393; c-PrCH 2, Me, c- PrCH 2], [RY394; c -PrCH 2, Me, Ph], [RY395; c-PrCH 2, Me, Bn], [RY396; c-PrCH 2, Me, CF 3], [RY397; c-PrCH 2, Me, CF 3 CH 2 ], [RY398; c-PrCH 2, Me, CF 3 CF 2], [RY399; c-PrCH 2, Me, CF 2 H], [RY400; c-PrCH 2, Me , CF 2 HCH 2 ],

[RY401;i-Bu,Me,Me],[RY402;i-Bu,Me,Et],[RY403;i-Bu,Me,Pr],[RY404;i-Bu,Me,i-Pr],[RY405;i-Bu,Me,c-Pr],[RY406;i-Bu,Me,t-Bu],[RY407;i-Bu,Me,Bu],[RY408;i-Bu,Me,t-Bu],[RY409;i-Bu,Me,c-PrCH2],[RY410;i-Bu,Me,Ph],[RY411;i-Bu,Me,Bn],[RY412;i-Bu,Me,CF3],[RY413;i-Bu,Me,CF3CH2],[RY414;i-Bu,Me,CF3CF2],[RY415;i-Bu,Me,CF2H],[RY416;i-Bu,Me,CF2HCH2],[RY417;CF3CH2,Me,Me],[RY418;CF3CH2,Me,Et],[RY419;CF3CH2,Me,Pr],[RY420;CF3CH2,Me,i-Pr],[RY421;CF3CH2,Me,c-Pr],[RY422;CF3CH2,Me,t-Bu],[RY423;CF3CH2,Me,Bu],[RY424;CF3CH2,Me,t-Bu],[RY425;CF3CH2,Me,c-PrCH2],[RY426;CF3CH2,Me,Ph],[RY427;CF3CH2,Me,Bn],[RY428;CF3CH2,Me,CF3],[RY429;CF3CH2,Me,CF3CH2],[RY430;CF3CH2,Me,CF3CF2],[RY431;CF3CH2,Me,CF2H],[RY432;CF3CH2,Me,CF2HCH2],[RY433;CF2HCH2,Me,Me],[RY434;CF2HCH2,Me,Et],[RY435;CF2HCH2,Me,Pr],[RY436;CF2HCH2,Me,i-Pr],[RY437;CF2HCH2,Me,c-Pr],[RY438;CF2HCH2,Me,t-Bu],[RY439;CF2HCH2,Me,Bu],[RY440;CF2HCH2,Me,t-Bu],[RY441;CF2HCH2,Me,c-PrCH2],[RY442;CF2HCH2,Me,Ph],[RY443;CF2HCH2,Me,Bn],[RY444;CF2HCH2,Me,CF3],[RY445;CF2HCH2,Me,CF3CH2],[RY446;CF2HCH2,Me,CF3CF2],[RY447;CF2HCH2,Me,CF2H],[RY448;CF2HCH2,Me,CF2HCH2],[RY449;MeOCH2,Me,Me],[RY450;MeOCH2,Me,Et],[RY451;MeOCH2,Me,Pr],[RY452;MeOCH2,Me,i-Pr],[RY453;MeOCH2,Me,c-Pr],[RY454;MeOCH2,Me,t-Bu],[RY455;MeOCH2,Me,Bu],[RY456;MeOCH2,Me,t-Bu],[RY457;MeOCH2,Me,c-PrCH2],[RY458;MeOCH2,Me,Ph],[RY459;MeOCH2,Me,Bn],[RY460;MeOCH2,Me,CF3],[RY461;MeOCH2,Me,CF3CH2],[RY462;MeOCH2,Me,CF3CF2],[RY463;MeOCH2,Me,CF2H],[RY464;MeOCH2,Me,CF2HCH2],[RY465;EtOCH2,Me,Me],[RY466;EtOCH2,Me,Et],[RY467;EtOCH2,Me,Pr],[RY468;EtOCH2,Me,i-Pr],[RY469;EtOCH2,Me,c-Pr],[RY470;EtOCH2,Me,t-Bu],[RY471;EtOCH2,Me,Bu],[RY472;EtOCH2,Me,t-Bu],[RY473;EtOCH2,Me,c-PrCH2],[RY474;EtOCH2,Me,Ph],[RY475;EtOCH2,Me,Bn],[RY476;EtOCH2,Me,CF3],[RY477;EtOCH2,Me,CF3CH2],[RY478;EtOCH2,Me,CF3CF2],[RY479;EtOCH2,Me,CF2H],[RY480;EtOCH2,Me,CF2HCH2],[RY481;MeSCH2,Me,Me],[RY482;MeSCH2,Me,Et],[RY483;MeSCH2,Me,Pr],[RY484;MeSCH2,Me,i-Pr],[RY485;MeSCH2,Me,c-Pr],[RY486;MeSCH2,Me,t-Bu],[RY487;MeSCH2,Me,Bu],[RY488;MeSCH2,Me,t-Bu],[RY489;MeSCH2,Me,c-PrCH2],[RY490;MeSCH2,Me,Ph],[RY491;MeSCH2,Me,Bn],[RY492;MeSCH2,Me,CF3],[RY493;MeSCH2,Me,CF3CH2],[RY494;MeSCH2,Me,CF3CF2],[RY495;MeSCH2,Me,CF2H],[RY496;MeSCH2,Me,CF2HCH2],[RY497;EtSCH2,Me,Me],[RY498;EtSCH2,Me,Et],[RY499;EtSCH2,Me,Pr],[RY500;EtSCH2,Me,i-Pr],[RY501;EtSCH2,Me,c-Pr],[RY502;EtSCH2,Me,t-Bu],[RY503;EtSCH2,Me,Bu],[RY504;EtSCH2,Me,t-Bu],[RY505;EtSCH2,Me,c-PrCH2],[RY506;EtSCH2,Me,Ph],[RY507;EtSCH2,Me,Bn],[RY508;EtSCH2,Me,CF3],[RY509;EtSCH2,Me,CF3CH2],[RY510;EtSCH2,Me,CF3CF2],[RY511;EtSCH2,Me,CF2H],[RY512;EtSCH2,Me,CF2HCH2],[RY513;Ph,Me,Me],[RY514;Ph,Me,Et],[RY515;Ph,Me,Pr],[RY516;Ph,Me,i-Pr],[RY517;Ph,Me,c-Pr],[RY518;Ph,Me,t-Bu],[RY519;Ph,Me,Bu],[RY520;Ph,Me,t-Bu],[RY521;Ph,Me,c-PrCH2],[RY522;Ph,Me,Ph],[RY523;Ph,Me,Bn],[RY524;Ph,Me,CF3],[RY525;Ph,Me,CF3CH2],[RY526;Ph,Me,CF3CF2],[RY527;Ph,Me,CF2H],[RY528;Ph,Me,CF2HCH2],[RY529;Bn,Me,Me],[RY530;Bn,Me,Et],[RY531;Bn,Me,Pr],[RY532;Bn,Me,i-Pr],[RY533;Bn,Me,c-Pr],[RY534;Bn,Me,t-Bu],[RY535;Bn,Me,Bu],[RY536;Bn,Me,t-Bu],[RY537;Bn,Me,c-PrCH2],[RY538;Bn,Me,Ph],[RY539;Bn,Me,Bn],[RY540;Bn,Me,CF3],[RY541;Bn,Me,CF3CH2],[RY542;Bn,Me,CF3CF2],[RY543;Bn,Me,CF2H],[RY544;Bn,Me,CF2HCH2],[RY545;HCCCH2,Me,Me],[RY546;HCCCH2,Me,Et],[RY547;HCCCH2,Me,Pr],[RY548;HCCCH2,Me,i-Pr],[RY549;HCCCH2,Me,c-Pr],[RY550;HCCCH2,Me,t-Bu],[RY551;HCCCH2,Me,Bu],[RY552;HCCCH2,Me,t-Bu],[RY553;HCCCH2,Me,c-PrCH2],[RY554;HCCCH2,Me,Ph],[RY555;HCCCH2,Me,Bn],[RY556;HCCCH2,Me,CF3],[RY557;HCCCH2,Me,CF3CH2],[RY558;HCCCH2,Me,CF3CF2],[RY559;HCCCH2,Me,CF2H],[RY560;HCCCH2,Me,CF2HCH2],[RY561;CH3CCCH2,Me,Me],[RY562;CH3CCCH2,Me,Et],[RY563;CH3CCCH2,Me,Pr],[RY564;CH3CCCH2,Me,i-Pr],[RY565;CH3CCCH2,Me,c-Pr],[RY566;CH3CCCH2,Me,t-Bu],[RY567;CH3CCCH2,Me,Bu],[RY568;CH3CCCH2,Me,t-Bu],[RY569;CH3CCCH2,Me,c-PrCH2],[RY570;CH3CCCH2,Me,Ph],[RY571;CH3CCCH2,Me,Bn],[RY572;CH3CCCH2,Me,CF3],[RY573;CH3CCCH2,Me,CF3CH2],[RY574;CH3CCCH2,Me,CF3CF2],[RY575;CH3CCCH2,Me,CF2H],[RY576;CH3CCCH2,Me,CF2HCH2],[RY577;H,Et,Et],[RY578;H,Et,Pr],[RY579;H,Et,i-Pr],[RY580;H,Et,c-Pr],[RY581;H,Et,t-Bu],[RY582;H,Et,Bu],[RY583;H,Et,t-Bu],[RY584;H,Et,c-PrCH2],[RY585;H,Et,Ph],[RY586;H,Et,Bn],[RY587;H,Et,CF3],[RY588;H,Et,CF3CH2],[RY589;H,Et,CF3CF2],[RY590;H,Et,CF2H],[RY591;H,Et,CF2HCH2],[RY592;Me,Et,Et],[RY593;Me,Et,Pr],[RY594;Me,Et,i-Pr],[RY595;Me,Et,c-Pr],[RY596;Me,Et,t-Bu],[RY597;Me,Et,Bu],[RY598;Me,Et,t-Bu],[RY599;Me,Et,c-PrCH2],[RY600;Me,Et,Ph], [RY 401; i-Bu, Me, Me], [RY 402; i-Bu, Me, Et], [RY 403; i-Bu, Me, Pr], [RY 404; i-Bu, Me, i-Pr], [RY 405; i-Bu, Me, c-Pr], [RY 406; i-Bu, Me, t-Bu], [RY 407; i-Bu, Me, Bu], [RY 408; i-Bu, Me, t -Bu], [RY 409; i-Bu, Me, c-PrCH 2 ], [RY 410; i-Bu, Me, Ph], [RY 411; i-Bu, Me, Bn], [RY 412; i-Bu, Me, CF 3 ], [RY 413; i-Bu, Me, CF 3 CH 2 ], [RY 414; i-Bu, Me, CF 3 CF 2 ], [RY 415; i-Bu, Me, CF 2 H], [RY 416; i-Bu, Me, CF 2 HCH 2 ], [RY 417; CF 3 CH 2 , Me, Me], [RY 418; CF 3 CH 2 , Me, Et], [RY 419; CF 3 CH 2 , Me , Pr], [RY 420; CF 3 CH 2 , Me, i-Pr], [RY 421; CF 3 CH 2 , Me, c-Pr], [RY 422; CF 3 CH 2 , Me, t-Bu], [RY RY423; CF 3 CH 2, Me , Bu], [RY424; CF 3 CH 2, Me, t-Bu], [RY425; CF 3 CH 2, Me, c-PrCH 2], [RY426; CF 3 CH 2 , Me, Ph], [RY 427; CF 3 CH 2 , Me, Bn], [RY 428; CF 3 CH 2 , Me, CF 3 ], [RY 429; CF 3 CH 2 , Me, CF 3 CH 2 ], [ RY430; CF 3 CH 2, Me , CF 3 CF 2], [RY431; CF 3 CH 2, Me, CF 2 H], [RY432; CF 3 CH 2, Me, CF 2 HCH 2], [RY433; CF 2 HCH 2 , Me, Me], [RY 434; CF 2 HCH 2 , Me, Et], [RY 435; CF 2 HCH 2 , Me, Pr], [RY 436; CF 2 HCH 2 , Me, i-Pr], [RY437; CF 2 HCH 2, Me, c-Pr], [RY438; CF 2 HCH 2, Me, t-Bu], [RY439; CF 2 HCH 2, Me, Bu], [RY440; CF 2 HC H 2, Me, t-Bu ], [RY441; CF 2 HCH 2, Me, c-PrCH 2], [RY442; CF 2 HCH 2, Me, Ph], [RY443; CF 2 HCH 2, Me, Bn ], [RY444; CF 2 HCH 2, Me, CF 3], [RY445; CF 2 HCH 2, Me, CF 3 CH 2], [RY446; CF 2 HCH 2, Me, CF 3 CF 2], [RY447 ; CF 2 HCH 2, Me, CF 2 H], [RY448; CF 2 HCH 2, Me, CF 2 HCH 2], [RY449; MeOCH 2, Me, Me], [RY450; MeOCH 2, Me, Et] , [RY 451; MeOCH 2 , Me, Pr], [RY 452; MeOCH 2 , Me, i-Pr], [RY 453; MeOCH 2 , Me, c-Pr], [RY 454; MeOCH 2 , Me, t-Bu] , [RY455; MeOCH 2, Me , Bu], [RY456; MeOCH 2, Me, t-Bu], [RY457; MeOCH 2, Me, c-PrCH 2], [RY458; MeOCH 2, Me, Ph], [RY459; MeOCH 2, Me, Bn], [RY460; MeOCH 2, Me, CF 3], [RY461; MeOCH 2, Me, CF 3 CH 2], [RY462; MeOCH 2, Me, CF 3 CF 2] , [RY463; MeOCH 2, Me , CF 2 H], [RY464; MeOCH 2, Me, CF 2 HCH 2], [RY465; EtOCH 2, Me, Me], [RY466; EtOCH 2, Me, Et], [RY 467; EtOCH 2 , Me, Pr], [RY 468; EtOCH 2 , Me, i-Pr], [RY 469; EtOCH 2 , Me, c-Pr], [RY 470; EtOCH 2 , Me, t-Bu], [RY 471; EtOCH 2 , Me, Bu], [RY 472; EtOCH 2 , Me, t-Bu], [RY 473; EtOCH 2 , Me, c-PrCH 2 ], [RY 474; EtOCH 2 , Me, Ph], [RY RY 475; EtOCH 2 , Me, Bn], [RY 476; EtOCH 2 , Me, CF 3 ], [RY 477; EtOCH 2 , Me, CF 3 CH 2 ] , [RY 478; EtOCH 2 , Me, CF 3 CF 2 ], [RY 479; EtOCH 2 , Me, CF 2 H], [RY 480; EtOCH 2 , Me, CF 2 HCH 2 ], [RY 481; MeSCH 2 , Me, Me], [RY 482; MeSCH 2 , Me, Et], [RY 483; MeSCH 2 , Me, Pr], [RY 484; MeSCH 2 , Me, i-Pr], [RY 485; MeSCH 2 , Me, c-Pr] , [RY486; MeSCH 2 , Me, t-Bu], [RY 487; MeSCH 2 , Me, Bu], [RY 488; MeSCH 2 , Me, t-Bu], [RY 489; MeSCH 2 , Me, c-PrCH 2 ], [RY 490; MeSCH 2 , Me, Ph], [RY 491; MeSCH 2 , Me, Bn], [RY 492; MeSCH 2 , Me, CF 3 ], [RY 493; MeSCH 2 , Me, CF 3 CH 2 ], [RY494; MeSCH 2, Me, CF 3 CF 2], [RY495; MeSCH 2, Me, CF 2 H], [RY496; MeSCH 2, Me, CF 2 HCH 2], [RY497; EtSCH 2, Me, Me ], [RY 498; EtSCH 2 , Me, Et], [RY 499; EtSCH 2 , Me, Pr], [RY 500; EtSCH 2 , Me, i-Pr], [RY 501; EtSCH 2 , Me, c-Pr], [RY502; EtSCH 2, Me, t-Bu], [RY503; EtSCH 2, Me, Bu], [RY504; EtSCH 2, Me, t-Bu], [RY505; EtSCH 2, Me, c-PrCH 2] , [RY506; EtSCH 2, Me , Ph], [RY507; EtSCH 2, Me, Bn], [RY508; EtSCH 2, Me, CF 3], [RY509; EtSCH 2, Me, CF 3 CH 2], [ RY510; EtSCH 2, Me, CF 3 CF 2], [RY511; EtSCH 2, Me, CF 2 H], [RY512; EtSCH 2, Me, CF 2 HCH 2], [RY513; Ph, Me, Me], [RY514; Ph, Me, Et], [RY 515; Ph, Me, Pr], [RY 516; Ph, Me, i-Pr], [RY 517; Ph , Me, c-Pr], [RY518; Ph, Me, t-Bu], [RY519; Ph, Me, Bu], [RY520; Ph, Me, t-Bu], [RY 521; Ph, Me, c -PrCH 2], [RY522; Ph , Me, Ph], [RY523; Ph, Me, Bn], [RY524; Ph, Me, CF 3], [RY525; Ph, Me, CF 3 CH 2], [ RY526; Ph, Me, CF 3 CF 2], [RY527; Ph, Me, CF 2 H], [RY528; Ph, Me, CF 2 HCH 2], [RY529; Bn, Me, Me], [RY530; Bn, Me, Et], [RY 531; Bn, Me, Pr], [RY 532: Bn, Me, i-Pr], [RY 533; Bn, Me, c-Pr], [RY 534; Bn, Me, t- Bu], [RY535; Bn, Me, Bu], [RY536; Bn, Me, t-Bu], [RY537; Bn, Me, c-PrCH 2], [RY538; Bn, Me, Ph], [RY539 ; Bn, Me, Bn], [RY540; Bn, Me, CF 3], [RY541; Bn, Me, CF 3 CH 2], [RY542; Bn, Me, CF 3 CF 2], [RY543; Bn, Me, CF 2 H], [ RY544; Bn, Me, CF 2 HCH 2], [RY545; HCCCH 2, Me, Me], [RY546; HCCCH 2, Me, Et], [RY547; HCCCH 2, Me, Pr], [RY548; HCCCH 2 , Me, i-Pr], [RY549; HCCCH 2, Me, c-Pr], [RY550; HCCCH 2, Me, t-Bu], [RY551; HCCCH 2, Me, Bu], [RY552; HCCCH 2 , Me, t-Bu], [RY553; HCCCH 2, Me, c-PrCH 2], [RY554; HCCCH 2, Me, Ph], [RY555; HCCCH 2, Me, Bn ], [RY 556; HCCCH 2 , Me, CF 3 ], [RY 557; HCCCH 2 , Me, CF 3 CH 2 ], [RY 558; HCCCH 2 , Me, CF 3 CF 2 ], [RY 559: HCCCH 2 , Me, CF 2 H], [RY 560; HCCCH 2 , Me, CF 2 HCH 2 ], [RY 561; CH 3 CCCH 2 , Me, Me] , [RY562; CH 3 CCCH 2 , Me, Et], [RY563; CH 3 CCCH 2, Me, Pr], [RY564; CH 3 CCCH 2, Me, i-Pr], [RY565; CH 3 CCCH 2, Me, c-Pr], [ RY566; CH 3 CCCH 2, Me, t-Bu], [RY567; CH 3 CCCH 2, Me, Bu], [RY568; CH 3 CCCH 2, Me, t-Bu], [RY569; CH 3 CCCH 2, Me, c-PrCH 2], [RY570; CH 3 CCCH 2, Me, Ph], [RY571; CH 3 CCCH 2, Me, Bn], [RY572; CH 3 CCCH 2, Me, CF 3], [RY573 ; CH 3 CCCH 2, Me, CF 3 CH 2], [RY574; CH 3 CCCH 2, Me, CF 3 CF 2], [RY575; CH 3 CCCH 2, Me, CF 2 H], [RY576; CH 3 CCCH 2, Me, CF 2 HCH 2], [RY577; H, Et, Et], [RY578; H, Et, Pr], [RY579; H, Et, i-Pr] , [RY 580; H, Et, c-Pr], [RY 581; H, Et, t-Bu], [RY 582; H, Et, Bu], [RY 583; H, Et, t-Bu], [RY 584; H, Et, c-PrCH 2 ], [RY585; H, Et, Ph], [RY586; H, Et, Bn], [RY587; H, Et, CF 3], [RY588; H, Et, CF 3 CH 2], [RY589; H , Et, CF 3 CF 2], [RY590; H, Et, CF 2 H], [RY591; H, Et, CF 2 HCH 2], [RY592; Me, Et, Et ], [RY593; Me, Et, Pr], [RY594; Me, Et, i-Pr], [RY595; Me, Et, c-Pr], [RY596; Me, Et, t-Bu], [RY 597] Me, Et, Bu], [RY 598; Me, Et, t-Bu], [RY 599; Me, Et, c-PrCH 2 ], [RY 600; Me, Et, Ph],

[RY601;Me,Et,Bn],[RY602;Me,Et,CF3],[RY603;Me,Et,CF3CH2],[RY604;Me,Et,CF3CF2],[RY605;Me,Et,CF2H],[RY606;Me,Et,CF2HCH2],[RY607;Et,Et,Et],[RY608;Et,Et,Pr],[RY609;Et,Et,i-Pr],[RY610;Et,Et,c-Pr],[RY611;Et,Et,t-Bu],[RY612;Et,Et,Bu],[RY613;Et,Et,t-Bu],[RY614;Et,Et,c-PrCH2],[RY615;Et,Et,Ph],[RY616;Et,Et,Bn],[RY617;Et,Et,CF3],[RY618;Et,Et,CF3CH2],[RY619;Et,Et,CF3CF2],[RY620;Et,Et,CF2H],[RY621;Et,Et,CF2HCH2],[RY622;Pr,Et,Et],[RY623;Pr,Et,Pr],[RY624;Pr,Et,i-Pr],[RY625;Pr,Et,c-Pr],[RY626;Pr,Et,t-Bu],[RY627;Pr,Et,Bu],[RY628;Pr,Et,t-Bu],[RY629;Pr,Et,c-PrCH2],[RY630;Pr,Et,Ph],[RY631;Pr,Et,Bn],[RY632;Pr,Et,CF3],[RY633;Pr,Et,CF3CH2],[RY634;Pr,Et,CF3CF2],[RY635;Pr,Et,CF2H],[RY636;Pr,Et,CF2HCH2],[RY637;i-Pr,Et,Et],[RY638;i-Pr,Et,Pr],[RY639;i-Pr,Et,i-Pr],[RY640;i-Pr,Et,c-Pr],[RY641;i-Pr,Et,t-Bu],[RY642;i-Pr,Et,Bu],[RY643;i-Pr,Et,t-Bu],[RY644;i-Pr,Et,c-PrCH2],[RY645;i-Pr,Et,Ph],[RY646;i-Pr,Et,Bn],[RY647;i-Pr,Et,CF3],[RY648;i-Pr,Et,CF3CH2],[RY649;i-Pr,Et,CF3CF2],[RY650;i-Pr,Et,CF2H],[RY651;i-Pr,Et,CF2HCH2],[RY652;c-Pr,Et,Et],[RY653;c-Pr,Et,Pr],[RY654;c-Pr,Et,i-Pr],[RY655;c-Pr,Et,c-Pr],[RY656;c-Pr,Et,t-Bu],[RY657;c-Pr,Et,Bu],[RY658;c-Pr,Et,t-Bu],[RY659;c-Pr,Et,c-PrCH2],[RY660;c-Pr,Et,Ph],[RY661;c-Pr,Et,Bn],[RY662;c-Pr,Et,CF3],[RY663;c-Pr,Et,CF3CH2],[RY664;c-Pr,Et,CF3CF2],[RY665;c-Pr,Et,CF2H],[RY666;c-Pr,Et,CF2HCH2],[RY667;c-PrCH2,Et,Et],[RY668;c-PrCH2,Et,Pr],[RY669;c-PrCH2,Et,i-Pr],[RY670;c-PrCH2,Et,c-Pr],[RY671;c-PrCH2,Et,t-Bu],[RY672;c-PrCH2,Et,Bu],[RY673;c-PrCH2,Et,t-Bu],[RY674;c-PrCH2,Et,c-PrCH2],[RY675;c-PrCH2,Et,Ph],[RY676;c-PrCH2,Et,Bn],[RY677;c-PrCH2,Et,CF3],[RY678;c-PrCH2,Et,CF3CH2],[RY679;c-PrCH2,Et,CF3CF2],[RY680;c-PrCH2,Et,CF2H],[RY681;c-PrCH2,Et,CF2HCH2],[RY682;i-Bu,Et,Et],[RY683;i-Bu,Et,Pr],[RY684;i-Bu,Et,i-Pr],[RY685;i-Bu,Et,c-Pr],[RY686;i-Bu,Et,t-Bu],[RY687;i-Bu,Et,Bu],[RY688;i-Bu,Et,t-Bu],[RY689;i-Bu,Et,c-PrCH2],[RY690;i-Bu,Et,Ph],[RY691;i-Bu,Et,Bn],[RY692;i-Bu,Et,CF3],[RY693;i-Bu,Et,CF3CH2],[RY694;i-Bu,Et,CF3CF2],[RY695;i-Bu,Et,CF2H],[RY696;i-Bu,Et,CF2HCH2],[RY697;CF3CH2,Et,Et],[RY698;CF3CH2,Et,Pr],[RY699;CF3CH2,Et,i-Pr],[RY700;CF3CH2,Et,c-Pr],[RY701;CF3CH2,Et,t-Bu],[RY702;CF3CH2,Et,Bu],[RY703;CF3CH2,Et,t-Bu],[RY704;CF3CH2,Et,c-PrCH2],[RY705;CF3CH2,Et,Ph],[RY706;CF3CH2,Et,Bn],[RY707;CF3CH2,Et,CF3],[RY708;CF3CH2,Et,CF3CH2],[RY709;CF3CH2,Et,CF3CF2],[RY710;CF3CH2,Et,CF2H],[RY711;CF3CH2,Et,CF2HCH2],[RY712;CF2HCH2,Et,Et],[RY713;CF2HCH2,Et,Pr],[RY714;CF2HCH2,Et,i-Pr],[RY715;CF2HCH2,Et,c-Pr],[RY716;CF2HCH2,Et,t-Bu],[RY717;CF2HCH2,Et,Bu],[RY718;CF2HCH2,Et,t-Bu],[RY719;CF2HCH2,Et,c-PrCH2],[RY720;CF2HCH2,Et,Ph],[RY721;CF2HCH2,Et,Bn],[RY722;CF2HCH2,Et,CF3],[RY723;CF2HCH2,Et,CF3CH2],[RY724;CF2HCH2,Et,CF3CF2],[RY725;CF2HCH2,Et,CF2H],[RY726;CF2HCH2,Et,CF2HCH2],[RY727;MeOCH2,Et,Et],[RY728;MeOCH2,Et,Pr],[RY729;MeOCH2,Et,i-Pr],[RY730;MeOCH2,Et,c-Pr],[RY731;MeOCH2,Et,t-Bu],[RY732;MeOCH2,Et,Bu],[RY733;MeOCH2,Et,t-Bu],[RY734;MeOCH2,Et,c-PrCH2],[RY735;MeOCH2,Et,Ph],[RY736;MeOCH2,Et,Bn],[RY737;MeOCH2,Et,CF3],[RY738;MeOCH2,Et,CF3CH2],[RY739;MeOCH2,Et,CF3CF2],[RY740;MeOCH2,Et,CF2H],[RY741;MeOCH2,Et,CF2HCH2],[RY742;EtOCH2,Et,Et],[RY743;EtOCH2,Et,Pr],[RY744;EtOCH2,Et,i-Pr],[RY745;EtOCH2,Et,c-Pr],[RY746;EtOCH2,Et,t-Bu],[RY747;EtOCH2,Et,Bu],[RY748;EtOCH2,Et,t-Bu],[RY749;EtOCH2,Et,c-PrCH2],[RY750;EtOCH2,Et,Ph],[RY751;EtOCH2,Et,Bn],[RY752;EtOCH2,Et,CF3],[RY753;EtOCH2,Et,CF3CH2],[RY754;EtOCH2,Et,CF3CF2],[RY755;EtOCH2,Et,CF2H],[RY756;EtOCH2,Et,CF2HCH2],[RY757;MeSCH2,Et,Et],[RY758;MeSCH2,Et,Pr],[RY759;MeSCH2,Et,i-Pr],[RY760;MeSCH2,Et,c-Pr],[RY761;MeSCH2,Et,t-Bu],[RY762;MeSCH2,Et,Bu],[RY763;MeSCH2,Et,t-Bu],[RY764;MeSCH2,Et,c-PrCH2],[RY765;MeSCH2,Et,Ph],[RY766;MeSCH2,Et,Bn],[RY767;MeSCH2,Et,CF3],[RY768;MeSCH2,Et,CF3CH2],[RY769;MeSCH2,Et,CF3CF2],[RY770;MeSCH2,Et,CF2H],[RY771;MeSCH2,Et,CF2HCH2],[RY772;EtSCH2,Et,Et],[RY773;EtSCH2,Et,Pr],[RY774;EtSCH2,Et,i-Pr],[RY775;EtSCH2,Et,c-Pr],[RY776;EtSCH2,Et,t-Bu],[RY777;EtSCH2,Et,Bu],[RY778;EtSCH2,Et,t-Bu],[RY779;EtSCH2,Et,c-PrCH2],[RY780;EtSCH2,Et,Ph],[RY781;EtSCH2,Et,Bn],[RY782;EtSCH2,Et,CF3],[RY783;EtSCH2,Et,CF3CH2],[RY784;EtSCH2,Et,CF3CF2],[RY785;EtSCH2,Et,CF2H],[RY786;EtSCH2,Et,CF2HCH2],[RY787;Ph,Et,Et],[RY788;Ph,Et,Pr],[RY789;Ph,Et,i-Pr],[RY790;Ph,Et,c-Pr],[RY791;Ph,Et,t-Bu],[RY792;Ph,Et,Bu],[RY793;Ph,Et,t-Bu],[RY794;Ph,Et,c-PrCH2],[RY795;Ph,Et,Ph],[RY796;Ph,Et,Bn],[RY797;Ph,Et,CF3],[RY798;Ph,Et,CF3CH2],[RY799;Ph,Et,CF3CF2],[RY800;Ph,Et,CF2H], [RY601; Me, Et, Bn ], [RY602; Me, Et, CF 3], [RY603; Me, Et, CF 3 CH 2], [RY604; Me, Et, CF 3 CF 2], [RY605; Me, Et, CF 2 H], [RY 606; Me, Et, CF 2 HCH 2 ], [RY 607; Et, Et, Et], [RY 608; Et, Et, Pr], [RY 609; Et, Et, i -Pr], [RY610; Et, Et, c-Pr], [RY611; Et, Et, t-Bu], [RY612; Et, Et, Bu], [RY613; Et, Et, t-Bu], [RY614; Et, Et, c -PrCH 2], [RY615; Et, Et, Ph], [RY616; Et, Et, Bn], [RY617; Et, Et, CF 3], [RY618; Et, Et , CF 3 CH 2 ], [RY 619; Et, Et, CF 3 CF 2 ], [RY 620; Et, Et, CF 2 H], [RY 621; Et, Et, CF 2 HCH 2 ], [RY 622; Pr, Et, Et], [RY 623; Pr, Et, Pr], [RY 624; Pr, Et, i-Pr], [RY 625; Pr, Et, c-Pr], [RY 626; Pr, Et, t-Bu] , [RY 627; Pr, Et, Bu], [RY 628; Pr, Et, t-Bu], [RY 629; Pr, Et, c-PrCH 2 ], [RY 630; Pr, Et, Ph], [RY 631; Pr , Et, Bn], [RY 632; Pr, Et, CF 3 ], [RY 633; Pr, Et, CF 3 CH 2 ], [RY 634; Pr, Et, CF 3 CF 2 ], [RY 635; Pr, Et, CF 2 H], [RY 636; Pr, Et, CF 2 HCH 2 ], [RY 637; i-Pr, Et, Et], [RY 638; i-Pr, Et, Pr], [RY 639; i-Pr, Et , i-Pr], [RY 640; i-Pr, Et, c-Pr], [RY 641; i-Pr, Et, t-Bu], [RY 642; i-Pr, Et, Bu], [RY 643; -Pr, Et, t-Bu], [RY 644; i-Pr, Et, c-PrCH 2 ], [RY 645; i-Pr, Et, Ph], [RY 646; i-Pr, Et, Bn], [ RY 647; i-Pr, Et, CF 3 ], [RY 648; i-Pr, Et, CF 3 CH 2 ], [RY 649; -Pr, Et, CF 3 CF 2 ], [RY650; i-Pr, Et, CF 2 H], [RY651; i-Pr, Et, CF 2 HCH 2], [RY652; c-Pr, Et, Et ], [RY 653; c-Pr, Et, Pr], [RY 654; c-Pr, Et, i-Pr], [RY 655; c-Pr, Et, c-Pr], [RY 656; c-Pr, Et , t-Bu], [RY657; c-Pr, Et, Bu], [RY658; c-Pr, Et, t-Bu], [RY 659; c-Pr, Et, c-PrCH 2 ], [RY 660; c-Pr, Et, Ph], [RY 661; c-Pr, Et, Bn], [RY 662; c-Pr, Et, CF 3 ], [RY 66; c-Pr, Et, CF 3 CH 2 ], [ RY664; c-Pr, Et, CF 3 CF 2], [RY665; c-Pr, Et, CF 2 H], [RY666; c-Pr, Et, CF 2 HCH 2], [RY667; c-PrCH 2 , Et, Et], [RY668 ; c-PrCH 2, Et, Pr], [RY669; c-PrCH 2, Et, i-Pr], [RY670; c-PrCH 2, Et, c-Pr], [ RY671; c-PrCH 2, Et , t-Bu], [RY672; c-PrCH 2, Et, Bu], [RY673; c-PrCH 2, Et, t-Bu], [RY674; c-PrCH 2, Et, c-PrCH 2], [RY675; c-PrCH 2, Et, Ph], [RY676; c-PrCH 2, Et, Bn], [RY677; c-PrCH 2, Et, CF 3], [RY678 ; c-PrCH 2, Et, CF 3 CH 2], [RY679; c-PrCH 2, Et, CF 3 CF 2], [RY680; c-PrCH 2, Et, CF 2 H], [RY681; c- PrCH 2, Et, CF 2 HCH 2], [RY682; i-Bu, Et, Et], [RY683; i-Bu, Et, Pr], [RY684; i-Bu, Et, i-Pr], [ RY 685; i-Bu, Et, c-Pr], [RY 686; i-Bu, Et, t-Bu], [RY 687; i-Bu, Et, Bu], [RY 688; i-Bu, Et, t- Bu], [RY 689; i-Bu, Et, c-PrCH 2 ], [RY 690; i-Bu, Et, Ph], [RY 69 1; i-Bu, Et, Bn], [RY 692; i-Bu, Et, CF 3 ], [RY 693; i-Bu, Et, CF 3 CH 2 ], [RY 694; i-Bu, Et, CF 3 CF 2 ], [RY 695; i-Bu, Et, CF 2 H], [RY 696; i-Bu, Et, CF 2 HCH 2 ], [RY 697; CF 3 CH 2 , Et, Et], [RY 698; CF 3 CH 2 , Et, Pr], [RY 699; CF 3 CH 2 , Et, i-Pr], [RY 700; CF 3 CH 2 , Et, c-Pr], [RY 701; CF 3 CH 2 , Et, t -Bu], [RY702; CF 3 CH 2, Et, Bu], [RY703; CF 3 CH 2, Et, t-Bu], [RY704; CF 3 CH 2, Et, c-PrCH 2], [RY705 ; CF 3 CH 2, Et, Ph], [RY706; CF 3 CH 2, Et, Bn], [RY707; CF 3 CH 2, Et, CF 3], [RY708; CF 3 CH 2, Et, CF 3 CH 2], [RY709; CF 3 CH 2, Et, CF 3 CF 2], [RY710; CF 3 CH 2, Et, CF 2 H], [RY711; CF 3 CH 2, Et, CF 2 HCH 2] , [RY712; CF 2 HCH 2 , Et, Et], [RY713; CF 2 HCH 2, Et, Pr], [RY714; CF 2 HCH 2, Et, i-Pr], [RY715; CF 2 HCH 2, Et, c-Pr], [ RY716; CF 2 HCH 2, Et, t-Bu], [RY717; CF 2 HCH 2, Et, Bu], [RY718; CF 2 HCH 2, Et, t-Bu], [RY719; CF 2 HCH 2, Et, c-PrCH 2], [RY720; CF 2 HCH 2, Et, Ph], [RY721; CF 2 HCH 2, Et, Bn], [RY722; CF 2 HCH 2, Et, CF 3], [RY723 ; CF 2 HCH 2, Et, CF 3 CH 2], [RY724; CF 2 HCH 2, Et, CF 3 CF 2], [RY725; CF 2 HCH 2, Et, CF 2 H], [RY726; CF 2 HCH 2, Et, CF 2 HCH 2], [RY727; MeOCH 2, Et, Et], [RY728; MeOCH 2, Et, Pr], [RY729; MeOCH 2, Et, i-Pr], [RY730; MeOCH 2, Et, c-Pr], [RY731 ; MeOCH 2, Et, t- Bu], [RY732; MeOCH 2, Et, Bu], [RY733; MeOCH 2, Et, t-Bu], [RY734; MeOCH 2, Et, c-PrCH 2], [ RY735; MeOCH 2, Et, Ph ], [RY736; MeOCH 2, Et, Bn], [RY737; MeOCH 2, Et, CF 3], [RY738; MeOCH 2, Et, CF 3 CH 2], [RY739; MeOCH 2, Et, CF 3 CF 2], [RY740; MeOCH 2, Et, CF 2 H], [RY741; MeOCH 2, Et, CF 2 HCH 2], [RY742; EtOCH 2, Et, Et], [ RY743; EtOCH 2, Et, Pr ], [RY744; EtOCH 2, Et, i-Pr], [RY745; EtOCH 2, Et, c-Pr], [RY746; EtOCH 2, Et, t-Bu], [ RY747; EtOCH 2, Et, Bu ], [RY748; EtOCH 2, Et, t-Bu], [RY749; EtOCH 2, Et, c-PrCH 2], [RY750; EtOCH 2, Et, Ph], [RY751 EtOCH 2 , Et, Bn], [RY 752; EtOCH 2 , Et, CF 3 ], [RY 753; EtOCH 2 , Et, CF 3 CH 2 ], [RY 754; EtOCH 2 , Et, CF 3 CF 2 ], [, RY755; EtOCH 2, Et, CF 2 H], [RY756; EtOCH 2, Et, CF 2 HCH 2], [RY757; MeSCH 2, Et, Et], [RY758; MeSCH 2, Et, Pr], [RY759 MeSCH 2 , Et, i-Pr], [RY 760; MeSCH 2 , Et, c-Pr], [RY 761; MeSCH 2 , Et, t-Bu], [RY 762; MeSCH 2 , Et, Bu], [RY 763 ; MeSCH 2, Et, t- Bu], [RY764; MeSCH 2, Et, c-PrCH 2], [RY765; MeSCH 2, E t, Ph], [RY766; MeSCH 2, Et, Bn], [RY767; MeSCH 2, Et, CF 3], [RY768; MeSCH 2, Et, CF 3 CH 2], [RY769; MeSCH 2, Et, CF 3 CF 2], [RY770 ; MeSCH 2, Et, CF 2 H], [RY771; MeSCH 2, Et, CF 2 HCH 2], [RY772; EtSCH 2, Et, Et], [RY773; EtSCH 2, Et, Pr], [RY774; EtSCH 2, Et, i-Pr], [RY775; EtSCH 2, Et, c-Pr], [RY776; EtSCH 2, Et, t-Bu], [RY777; EtSCH 2, Et, Bu], [RY 778; EtSCH 2 , Et, t-Bu], [RY 779; EtSCH 2 , Et, c-PrCH 2 ], [RY 780; EtSCH 2 , Et, Ph], [RY 781; EtSCH 2 , Et Et 2 , Bn], [RY782; EtSCH 2, Et, CF 3], [RY783; EtSCH 2, Et, CF 3 CH 2], [RY784; EtSCH 2, Et, CF 3 CF 2], [RY785; EtSCH 2, Et, CF 2 H], [ RY786; EtSCH 2, Et, CF 2 HCH 2], [RY787; Ph, Et, Et], [RY788; Ph, Et, Pr], [RY789; Ph, Et, i- Pr], [RY 790; Ph, Et, c-Pr], [RY 791; Ph, Et, t-Bu], [RY 792; Ph, Et, Bu], [RY 793; Ph, Et, t-Bu], [ RY794; Ph, Et, c- PrCH 2], [RY795; Ph, Et, Ph], [RY796; Ph, Et, Bn], [RY797; Ph, Et, CF 3], [RY798; Ph, Et, CF 3 CH 2], [RY799 ; Ph, Et, CF 3 CF 2], [RY800; Ph, Et, CF 2 H],

[RY801;Ph,Et,CF2HCH2],[RY802;Bn,Et,Et],[RY803;Bn,Et,Pr],[RY804;Bn,Et,i-Pr],[RY805;Bn,Et,c-Pr],[RY806;Bn,Et,t-Bu],[RY807;Bn,Et,Bu],[RY808;Bn,Et,t-Bu],[RY809;Bn,Et,c-PrCH2],[RY810;Bn,Et,Ph],[RY811;Bn,Et,Bn],[RY812;Bn,Et,CF3],[RY813;Bn,Et,CF3CH2],[RY814;Bn,Et,CF3CF2],[RY815;Bn,Et,CF2H],[RY816;Bn,Et,CF2HCH2],[RY817;HCCCH2,Et,Et],[RY818;HCCCH2,Et,Pr],[RY819;HCCCH2,Et,i-Pr],[RY820;HCCCH2,Et,c-Pr],[RY821;HCCCH2,Et,t-Bu],[RY822;HCCCH2,Et,Bu],[RY823;HCCCH2,Et,t-Bu],[RY824;HCCCH2,Et,c-PrCH2],[RY825;HCCCH2,Et,Ph],[RY826;HCCCH2,Et,Bn],[RY827;HCCCH2,Et,CF3],[RY828;HCCCH2,Et,CF3CH2],[RY829;HCCCH2,Et,CF3CF2],[RY830;HCCCH2,Et,CF2H],[RY831;HCCCH2,Et,CF2HCH2],[RY832;CH3CCCH2,Et,Et],[RY833;CH3CCCH2,Et,Pr],[RY834;CH3CCCH2,Et,i-Pr],[RY835;CH3CCCH2,Et,c-Pr],[RY836;CH3CCCH2,Et,t-Bu],[RY837;CH3CCCH2,Et,Bu],[RY838;CH3CCCH2,Et,t-Bu],[RY839;CH3CCCH2,Et,c-PrCH2],[RY840;CH3CCCH2,Et,Ph],[RY841;CH3CCCH2,Et,Bn],[RY842;CH3CCCH2,Et,CF3],[RY843;CH3CCCH2,Et,CF3CH2],[RY844;CH3CCCH2,Et,CF3CF2],[RY845;CH3CCCH2,Et,CF2H],[RY846;CH3CCCH2,Et,CF2HCH2],[RY847;H,Pr,Pr],[RY848;H,Pr,i-Pr],[RY849;H,Pr,c-Pr],[RY850;H,Pr,t-Bu],[RY851;H,Pr,Bu],[RY852;H,Pr,t-Bu],[RY853;H,Pr,c-PrCH2],[RY854;H,Pr,Ph],[RY855;H,Pr,Bn],[RY856;H,Pr,CF3],[RY857;H,Pr,CF3CH2],[RY858;H,Pr,CF3CF2],[RY859;H,Pr,CF2H],[RY860;H,Pr,CF2HCH2],[RY861;Me,Pr,Me],[RY862;Me,Pr,Et],[RY863;Me,Pr,Pr],[RY864;Me,Pr,i-Pr],[RY865;Me,Pr,c-Pr],[RY866;Me,Pr,t-Bu],[RY867;Me,Pr,Bu],[RY868;Me,Pr,t-Bu],[RY869;Me,Pr,c-PrCH2],[RY870;Me,Pr,Ph],[RY871;Me,Pr,Bn],[RY872;Me,Pr,CF3],[RY873;Me,Pr,CF3CH2],[RY874;Me,Pr,CF3CF2],[RY875;Me,Pr,CF2H],[RY876;Me,Pr,CF2HCH2],[RY877;Et,Pr,Pr],[RY878;Et,Pr,i-Pr],[RY879;Et,Pr,c-Pr],[RY880;Et,Pr,t-Bu],[RY881;Et,Pr,Bu],[RY882;Et,Pr,t-Bu],[RY883;Et,Pr,c-PrCH2],[RY884;Et,Pr,Ph],[RY885;Et,Pr,Bn],[RY886;Et,Pr,CF3],[RY887;Et,Pr,CF3CH2],[RY888;Et,Pr,CF3CF2],[RY889;Et,Pr,CF2H],[RY890;Et,Pr,CF2HCH2],[RY891;Pr,Pr,Pr],[RY892;Pr,Pr,i-Pr],[RY893;Pr,Pr,c-Pr],[RY894;Pr,Pr,t-Bu],[RY895;Pr,Pr,Bu],[RY896;Pr,Pr,t-Bu],[RY897;Pr,Pr,c-PrCH2],[RY898;Pr,Pr,Ph],[RY899;Pr,Pr,Bn],[RY900;Pr,Pr,CF3],[RY901;Pr,Pr,CF3CH2],[RY902;Pr,Pr,CF3CF2],[RY903;Pr,Pr,CF2H],[RY904;Pr,Pr,CF2HCH2],[RY905;i-Pr,Pr,Pr],[RY906;i-Pr,Pr,i-Pr],[RY907;i-Pr,Pr,c-Pr],[RY908;i-Pr,Pr,t-Bu],[RY909;i-Pr,Pr,Bu],[RY910;i-Pr,Pr,t-Bu],[RY911;i-Pr,Pr,c-PrCH2],[RY912;i-Pr,Pr,Ph],[RY913;i-Pr,Pr,Bn],[RY914;i-Pr,Pr,CF3],[RY915;i-Pr,Pr,CF3CH2],[RY916;i-Pr,Pr,CF3CF2],[RY917;i-Pr,Pr,CF2H],[RY918;i-Pr,Pr,CF2HCH2],[RY919;c-Pr,Pr,Pr],[RY920;c-Pr,Pr,i-Pr],[RY921;c-Pr,Pr,c-Pr],[RY922;c-Pr,Pr,t-Bu],[RY923;c-Pr,Pr,Bu],[RY924;c-Pr,Pr,t-Bu],[RY925;c-Pr,Pr,c-PrCH2],[RY926;c-Pr,Pr,Ph],[RY927;c-Pr,Pr,Bn],[RY928;c-Pr,Pr,CF3],[RY929;c-Pr,Pr,CF3CH2],[RY930;c-Pr,Pr,CF3CF2],[RY931;c-Pr,Pr,CF2H],[RY932;c-Pr,Pr,CF2HCH2],[RY933;c-PrCH2,Pr,Pr],[RY934;c-PrCH2,Pr,i-Pr],[RY935;c-PrCH2,Pr,c-Pr],[RY936;c-PrCH2,Pr,t-Bu],[RY937;c-PrCH2,Pr,Bu],[RY938;c-PrCH2,Pr,t-Bu],[RY939;c-PrCH2,Pr,c-PrCH2],[RY940;c-PrCH2,Pr,Ph],[RY941;c-PrCH2,Pr,Bn],[RY942;c-PrCH2,Pr,CF3],[RY943;c-PrCH2,Pr,CF3CH2],[RY944;c-PrCH2,Pr,CF3CF2],[RY945;c-PrCH2,Pr,CF2H],[RY946;c-PrCH2,Pr,CF2HCH2],[RY947;i-Bu,Pr,Pr],[RY948;i-Bu,Pr,i-Pr],[RY949;i-Bu,Pr,c-Pr],[RY950;i-Bu,Pr,t-Bu],[RY951;i-Bu,Pr,Bu],[RY952;i-Bu,Pr,t-Bu],[RY953;i-Bu,Pr,c-PrCH2],[RY954;i-Bu,Pr,Ph],[RY955;i-Bu,Pr,Bn],[RY956;i-Bu,Pr,CF3],[RY957;i-Bu,Pr,CF3CH2],[RY958;i-Bu,Pr,CF3CF2],[RY959;i-Bu,Pr,CF2H],[RY960;i-Bu,Pr,CF2HCH2],[RY961;CF3CH2,Pr,Pr],[RY962;CF3CH2,Pr,i-Pr],[RY963;CF3CH2,Pr,c-Pr],[RY964;CF3CH2,Pr,t-Bu],[RY965;CF3CH2,Pr,Bu],[RY966;CF3CH2,Pr,t-Bu],[RY967;CF3CH2,Pr,c-PrCH2],[RY968;CF3CH2,Pr,Ph],[RY969;CF3CH2,Pr,Bn],[RY970;CF3CH2,Pr,CF3],[RY971;CF3CH2,Pr,CF3CH2],[RY972;CF3CH2,Pr,CF3CF2],[RY973;CF3CH2,Pr,CF2H],[RY974;CF3CH2,Pr,CF2HCH2],[RY975;CF2HCH2,Pr,Pr],[RY976;CF2HCH2,Pr,i-Pr],[RY977;CF2HCH2,Pr,c-Pr],[RY978;CF2HCH2,Pr,t-Bu],[RY979;CF2HCH2,Pr,Bu],[RY980;CF2HCH2,Pr,t-Bu],[RY981;CF2HCH2,Pr,c-PrCH2],[RY982;CF2HCH2,Pr,Ph],[RY983;CF2HCH2,Pr,Bn],[RY984;CF2HCH2,Pr,CF3],[RY985;CF2HCH2,Pr,CF3CH2],[RY986;CF2HCH2,Pr,CF3CF2],[RY987;CF2HCH2,Pr,CF2H],[RY988;CF2HCH2,Pr,CF2HCH2],[RY989;MeOCH2,Pr,Pr],[RY990;MeOCH2,Pr,i-Pr],[RY991;MeOCH2,Pr,c-Pr],[RY992;MeOCH2,Pr,t-Bu],[RY993;MeOCH2,Pr,Bu],[RY994;MeOCH2,Pr,t-Bu],[RY995;MeOCH2,Pr,c-PrCH2],[RY996;MeOCH2,Pr,Ph],[RY997;MeOCH2,Pr,Bn],[RY998;MeOCH2,Pr,CF3],[RY999;MeOCH2,Pr,CF3CH2],[RY1000;MeOCH2,Pr,CF3CF2], [RY801; Ph, Et, CF 2 HCH 2], [RY802; Bn, Et, Et], [RY803; Bn, Et, Pr], [RY804; Bn, Et, i-Pr], [RY805; Bn, Et, c-Pr], [RY 806; Bn, Et, t-Bu], [RY 807; Bn, Et, Bu], [RY 808; Bn, Et, t-Bu], [RY 809; Bn, Et, c- PrCH 2], [RY810; Bn , Et, Ph], [RY811; Bn, Et, Bn], [RY812; Bn, Et, CF 3], [RY813; Bn, Et, CF 3 CH 2], [RY814 ; Bn, Et, CF 3 CF 2], [RY815; Bn, Et, CF 2 H], [RY816; Bn, Et, CF 2 HCH 2], [RY817; HCCCH 2, Et, Et], [RY818; HCCCH 2, Et, Pr], [RY819; HCCCH 2, Et, i-Pr], [RY820; HCCCH 2, Et, c-Pr], [RY821; HCCCH 2, Et, t-Bu], [RY822; HCCCH 2, Et, Bu], [RY823; HCCCH 2, Et, t-Bu], [RY824; HCCCH 2, Et, c-PrCH 2], [RY825; HCCCH 2, Et, Ph], [RY826; HCCCH 2, Et, Bn], [ RY827; HCCCH 2, Et, CF 3], [RY828; HCCCH 2, Et, CF 3 CH 2], [RY829; HCCCH 2, Et, CF 3 CF 2], [RY830; HCCCH 2, Et, CF 2 H ], [RY831; HCCCH 2, Et, CF 2 HCH 2], [RY832; CH 3 CCCH 2, Et, Et], [RY833; CH 3 CCCH 2, Et, Pr], [RY834; CH 3 CCCH 2, Et, i-Pr], [RY835; CH 3 CCCH 2, Et, c-Pr], [RY836; CH 3 CCCH 2, Et, t-Bu], [RY837; CH 3 CCCH 2, Et, Bu], [RY838; CH 3 CCCH 2, Et, t-Bu], [RY839; CH 3 CCCH 2, Et, c-PrCH 2], [RY840; CH 3 CCCH 2, Et, Ph ], [RY 841; CH 3 CCCH 2 , Et , Bn], [RY842; CH 3 CCCH 2, Et, CF 3], [RY843; CH 3 CCCH 2, Et, CF 3 CH 2], [RY844; CH 3 CCCH 2, Et, CF 3 CF 2], [RY845; CH 3 CCCH 2, Et, CF 2 H], [RY846; CH 3 CCCH 2, Et, CF 2 HCH 2], [RY847; H, Pr, Pr], [RY848; H, Pr, i- H, Pr, c-Pr], [RY 850; H, Pr, t-Bu], [RY 851; H, Pr, Bu], [RY 852; H, Pr, t-Bu], [Pr 8] RY853; H, Pr, c- PrCH 2], [RY854; H, Pr, Ph], [RY855; H, Pr, Bn], [RY856; H, Pr, CF 3], [RY857; H, Pr, CF 3 CH 2 ], [RY 858; H, Pr, CF 3 CF 2 ], [RY 859; H, Pr, CF 2 H], [RY 860; H, Pr, CF 2 HCH 2 ], [RY 861; Me, Pr , Me], [RY 862; Me, Pr, Et], [RY 863; Me, Pr, Pr], [RY 864; Me, Pr, i-Pr], [RY 865; Me, Pr, c-Pr], [RY 866 Me, Pr, t-Bu], [RY867; Me, Pr, Bu], [RY 868; Me, Pr, t-Bu], [RY 869; Me, Pr, c-PrCH 2 ], [RY 870; Me, Pr, Ph], [RY 871; Me, Pr, Bn], [RY 872; Me, Pr, CF 3 ], [RY 873; Me, Pr, CF 3 CH 2 ], [RY 874; Me, Pr, CF 3 CF 2 ], [RY 875; Me, Pr, CF 2 H], [RY 876; Me, Pr, CF 2 HCH 2 ], [RY 877; Et, Pr, Pr], [RY 878; Et, Pr, i-Pr], [ RY 879; Et, Pr, c-Pr], [RY 880; Et, Pr, t-Bu], [RY 881; Et, Pr, Bu], [RY 882; Et, Pr, t-Bu], [RY 883; Et, Pr, c-PrCH 2], [RY884; Et, Pr, Ph], [RY885; Et, Pr, Bn], [RY886; Et, Pr, CF 3], [RY887; Et, Pr, CF 3 CH 2 ], [RY 888; Et, Pr, CF 3 CF 2 ], [RY889; Et, Pr, CF 2 H], [RY890; Et, Pr, CF 2 HCH 2], [RY891; Pr, Pr, Pr], [RY892; Pr, Pr, i-Pr], [RY893; Pr, Pr, c-Pr], [RY 894; Pr, Pr, t-Bu], [RY 895; Pr, Pr, Bu], [RY 896; Pr, Pr, t-Bu], [RY 897; Pr, Pr, c-PrCH 2], [RY898 ; Pr, Pr, Ph], [RY899; Pr, Pr, Bn], [RY900; Pr, Pr, CF 3], [RY901; Pr, Pr, CF 3 CH 2], [RY902; Pr, Pr, CF 3 CF 2], [RY903; Pr, Pr, CF 2 H], [RY904; Pr, Pr, CF 2 HCH 2], [RY905; i-Pr, Pr, Pr], [RY906; i-Pr, Pr, i-Pr], [RY 907; i-Pr, Pr, c-Pr], [RY 908; i-Pr, Pr, t-Bu], [RY 909; i-Pr, Pr , Bu], [RY 910; i-Pr, Pr, t-Bu], [RY 911; i-Pr, Pr, c-PrCH 2 ], [RY 912; i-Pr, Pr, Ph], [RY 913; Pr, Pr, Bn], [RY 914; i-Pr, Pr, CF 3 ], [RY 915; i-Pr, Pr, CF 3 CH 2 ], [RY 916; i-Pr, Pr, CF 3 CF 2 ], [RY917; i-Pr, Pr , CF 2 H], [RY918; i-Pr, Pr, CF 2 HCH 2], [RY919; c-Pr, Pr, Pr], [RY920; c-Pr, Pr, i-Pr], [RY 921; c-Pr, Pr, c-Pr], [RY 922; c-Pr, Pr, t-Bu], [RY 923; c-Pr, Pr, Bu], [RY 924; c- Pr, Pr, t-Bu], [RY 925; c-Pr, Pr, c-PrCH 2 ], [RY 926; c-Pr, Pr, Ph], [RY 927; c-Pr, Pr, Bn], [RY 928 c-Pr, Pr, CF 3 ], [RY 929; c-Pr, Pr, CF 3 CH 2 ], [RY 930; c-Pr, Pr, CF 3 CF 2 ], [RY 931; c-Pr, Pr, CF 2 H], [RY932; c-Pr, Pr, CF 2 HCH 2], [RY933; c-PrCH 2, Pr, Pr], [RY934; c-PrCH 2, P r, i-Pr], [ RY935; c-PrCH 2, Pr, c-Pr], [RY936; c-PrCH 2, Pr, t-Bu], [RY937; c-PrCH 2, Pr, Bu], [RY938; c-PrCH 2, Pr, t-Bu], [RY939; c-PrCH 2, Pr, c-PrCH 2], [RY940; c-PrCH 2, Pr, Ph], [RY941; c-PrCH 2, Pr, Bn], [ RY942; c-PrCH 2, Pr, CF 3], [RY943; c-PrCH 2, Pr, CF 3 CH 2], [RY944; c-PrCH 2, Pr, CF 3 CF 2], [RY945; c- PrCH 2, Pr, CF 2 H], [RY946; c-PrCH 2, Pr, CF 2 HCH 2], [RY947; i-Bu, Pr, Pr], [RY948; i -Bu, Pr, i-Pr], [RY949; i-Bu, Pr, c-Pr], [RY950; i-Bu, Pr, t-Bu], [RY951; i-Bu, Pr, Bu], [RY952; i-Bu, Pr , t-Bu], [RY953; i-Bu, Pr, c-PrCH 2], [RY954; i-Bu, Pr, Ph], [RY955; i-Bu, Pr, bn], [RY956; i- Bu, Pr, CF 3], [RY957; i-Bu, Pr, CF 3 CH 2], [RY958; i-Bu, Pr, CF 3 CF 2], [RY959; i -Bu, Pr, CF 2 H] , [RY960; i-Bu, Pr, CF 2 HCH 2], [RY961; CF 3 CH 2, Pr, Pr], [RY962; CF 3 CH 2, Pr, i- Pr], [RY963; CF 3 CH 2, Pr, c-Pr], [RY964; CF 3 CH 2, Pr, t-Bu], [RY965; CF 3 CH 2, Pr, Bu], [RY966; CF 3 CH 2 , Pr, t-Bu], [RY 967; CF 3 CH 2 , Pr, c-Pr CH 2 ], [RY 968; CF 3 CH 2 , Pr, Ph], [RY 969; CF 3 CH 2 , Pr, bn], [RY970; CF 3 CH 2, Pr, CF 3], [RY971; CF 3 CH 2, Pr, CF 3 CH 2], [RY972; CF 3 CH 2, Pr, CF 3 CF 2], [ RY 973; CF 3 CH 2, Pr, CF 2 H ], [RY974; CF 3 CH 2, Pr, CF 2 HCH 2], [RY975; CF 2 HCH 2, Pr, Pr], [RY976; CF 2 HCH 2, Pr, i -Pr], [RY977; CF 2 HCH 2, Pr, c-Pr], [RY978; CF 2 HCH 2, Pr, t-Bu], [RY979; CF 2 HCH 2, Pr, Bu], [RY980; CF 2 HCH 2, Pr, t -Bu], [RY981; CF 2 HCH 2, Pr, c-PrCH 2], [RY982; CF 2 HCH 2, Pr, Ph], [RY983; CF 2 HCH 2, Pr , Bn], [RY984; CF 2 HCH 2, Pr, CF 3], [RY985; CF 2 HCH 2, Pr, CF 3 CH 2], [RY986; CF 2 HCH 2, Pr, CF 3 CF 2], [RY987; CF 2 HCH 2, Pr, CF 2 H], [RY988; CF 2 HCH 2, Pr, CF 2 HCH 2], [RY989; MeOCH 2, Pr, Pr], [RY990; MeOCH 2, Pr, i-Pr], [RY991; MeOCH 2, Pr, c-Pr], [RY992; MeOCH 2, Pr, t-Bu], [RY993; MeOCH 2, Pr, Bu], [RY994; MeOCH 2, Pr, t-Bu], [RY995; MeOCH 2, Pr, c-PrCH 2], [RY996; MeOCH 2, Pr, Ph], [RY997; MeOCH 2, Pr, Bn], [RY998; MeOCH 2, Pr, CF 3 ], [RY 999; MeOCH 2 , Pr, CF 3 CH 2 ], [RY 1000; MeOCH 2 , Pr, CF 3 CF 2 ],

[RY1001;MeOCH2,Pr,CF2H],[RY1002;MeOCH2,Pr,CF2HCH2],[RY1003;EtOCH2,Pr,Pr],[RY1004;EtOCH2,Pr,i-Pr],[RY1005;EtOCH2,Pr,c-Pr],[RY1006;EtOCH2,Pr,t-Bu],[RY1007;EtOCH2,Pr,Bu],[RY1008;EtOCH2,Pr,t-Bu],[RY1009;EtOCH2,Pr,c-PrCH2],[RY1010;EtOCH2,Pr,Ph],[RY1011;EtOCH2,Pr,Bn],[RY1012;EtOCH2,Pr,CF3],[RY1013;EtOCH2,Pr,CF3CH2],[RY1014;EtOCH2,Pr,CF3CF2],[RY1015;EtOCH2,Pr,CF2H],[RY1016;EtOCH2,Pr,CF2HCH2],[RY1017;MeSCH2,Pr,Pr],[RY1018;MeSCH2,Pr,i-Pr],[RY1019;MeSCH2,Pr,c-Pr],[RY1020;MeSCH2,Pr,t-Bu],[RY1021;MeSCH2,Pr,Bu],[RY1022;MeSCH2,Pr,t-Bu],[RY1023;MeSCH2,Pr,c-PrCH2],[RY1024;MeSCH2,Pr,Ph],[RY1025;MeSCH2,Pr,Bn],[RY1026;MeSCH2,Pr,CF3],[RY1027;MeSCH2,Pr,CF3CH2],[RY1028;MeSCH2,Pr,CF3CF2],[RY1029;MeSCH2,Pr,CF2H],[RY1030;MeSCH2,Pr,CF2HCH2],[RY1031;EtSCH2,Pr,Pr],[RY1032;EtSCH2,Pr,i-Pr],[RY1033;EtSCH2,Pr,c-Pr],[RY1034;EtSCH2,Pr,t-Bu],[RY1035;EtSCH2,Pr,Bu],[RY1036;EtSCH2,Pr,t-Bu],[RY1037;EtSCH2,Pr,c-PrCH2],[RY1038;EtSCH2,Pr,Ph],[RY1039;EtSCH2,Pr,Bn],[RY1040;EtSCH2,Pr,CF3],[RY1041;EtSCH2,Pr,CF3CH2],[RY1042;EtSCH2,Pr,CF3CF2],[RY1043;EtSCH2,Pr,CF2H],[RY1044;EtSCH2,Pr,CF2HCH2],[RY1045;Ph,Pr,Pr],[RY1046;Ph,Pr,i-Pr],[RY1047;Ph,Pr,c-Pr],[RY1048;Ph,Pr,t-Bu],[RY1049;Ph,Pr,Bu],[RY1050;Ph,Pr,t-Bu],[RY1051;Ph,Pr,c-PrCH2],[RY1052;Ph,Pr,Ph],[RY1053;Ph,Pr,Bn],[RY1054;Ph,Pr,CF3],[RY1055;Ph,Pr,CF3CH2],[RY1056;Ph,Pr,CF3CF2],[RY1057;Ph,Pr,CF2H],[RY1058;Ph,Pr,CF2HCH2],[RY1059;Bn,Pr,Pr],[RY1060;Bn,Pr,i-Pr],[RY1061;Bn,Pr,c-Pr],[RY1062;Bn,Pr,t-Bu],[RY1063;Bn,Pr,Bu],[RY1064;Bn,Pr,t-Bu],[RY1065;Bn,Pr,c-PrCH2],[RY1066;Bn,Pr,Ph],[RY1067;Bn,Pr,Bn],[RY1068;Bn,Pr,CF3],[RY1069;Bn,Pr,CF3CH2],[RY1070;Bn,Pr,CF3CF2],[RY1071;Bn,Pr,CF2H],[RY1072;Bn,Pr,CF2HCH2],[RY1073;HCCCH2,Pr,Pr],[RY1074;HCCCH2,Pr,i-Pr],[RY1075;HCCCH2,Pr,c-Pr],[RY1076;HCCCH2,Pr,t-Bu],[RY1077;HCCCH2,Pr,Bu],[RY1078;HCCCH2,Pr,t-Bu],[RY1079;HCCCH2,Pr,c-PrCH2],[RY1080;HCCCH2,Pr,Ph],[RY1081;HCCCH2,Pr,Bn],[RY1082;HCCCH2,Pr,CF3],[RY1083;HCCCH2,Pr,CF3CH2],[RY1084;HCCCH2,Pr,CF3CF2],[RY1085;HCCCH2,Pr,CF2H],[RY1086;HCCCH2,Pr,CF2HCH2],[RY1087;CH3CCCH2,Pr,Pr],[RY1088;CH3CCCH2,Pr,i-Pr],[RY1089;CH3CCCH2,Pr,c-Pr],[RY1090;CH3CCCH2,Pr,t-Bu],[RY1091;CH3CCCH2,Pr,Bu],[RY1092;CH3CCCH2,Pr,t-Bu],[RY1093;CH3CCCH2,Pr,c-PrCH2],[RY1094;CH3CCCH2,Pr,Ph],[RY1095;CH3CCCH2,Pr,Bn],[RY1096;CH3CCCH2,Pr,CF3],[RY1097;CH3CCCH2,Pr,CF3CH2],[RY1098;CH3CCCH2,Pr,CF3CF2],[RY1099;CH3CCCH2,Pr,CF2H],[RY1100;CH3CCCH2,Pr,CF2HCH2],[RY1101;H,i-Pr,i-Pr],[RY1102;H,i-Pr,c-Pr],[RY1103;H,i-Pr,t-Bu],[RY1104;H,i-Pr,Bu],[RY1105;H,i-Pr,t-Bu],[RY1106;H,i-Pr,c-PrCH2],[RY1107;H,i-Pr,Ph],[RY1108;H,i-Pr,Bn],[RY1109;H,i-Pr,CF3],[RY1110;H,i-Pr,CF3CH2],[RY1111;H,i-Pr,CF3CF2],[RY1112;H,i-Pr,CF2H],[RY1113;H,i-Pr,CF2HCH2],[RY1114;Me,i-Pr,i-Pr],[RY1115;Me,i-Pr,c-Pr],[RY1116;Me,i-Pr,t-Bu],[RY1117;Me,i-Pr,Bu],[RY1118;Me,i-Pr,t-Bu],[RY1119;Me,i-Pr,c-PrCH2],[RY1120;Me,i-Pr,Ph],[RY1121;Me,i-Pr,Bn],[RY1122;Me,i-Pr,CF3],[RY1123;Me,i-Pr,CF3CH2],[RY1124;Me,i-Pr,CF3CF2],[RY1125;Me,i-Pr,CF2H],[RY1126;Me,i-Pr,CF2HCH2],[RY1127;Et,i-Pr,i-Pr],[RY1128;Et,i-Pr,c-Pr],[RY1129;Et,i-Pr,t-Bu],[RY1130;Et,i-Pr,Bu],[RY1131;Et,i-Pr,t-Bu],[RY1132;Et,i-Pr,c-PrCH2],[RY1133;Et,i-Pr,Ph],[RY1134;Et,i-Pr,Bn],[RY1135;Et,i-Pr,CF3],[RY1136;Et,i-Pr,CF3CH2],[RY1137;Et,i-Pr,CF3CF2],[RY1138;Et,i-Pr,CF2H],[RY1139;Et,i-Pr,CF2HCH2],[RY1140;Pr,i-Pr,i-Pr],[RY1141;Pr,i-Pr,c-Pr],[RY1142;Pr,i-Pr,t-Bu],[RY1143;Pr,i-Pr,Bu],[RY1144;Pr,i-Pr,t-Bu],[RY1145;Pr,i-Pr,c-PrCH2],[RY1146;Pr,i-Pr,Ph],[RY1147;Pr,i-Pr,Bn],[RY1148;Pr,i-Pr,CF3],[RY1149;Pr,i-Pr,CF3CH2],[RY1150;Pr,i-Pr,CF3CF2],[RY1151;Pr,i-Pr,CF2H],[RY1152;Pr,i-Pr,CF2HCH2],[RY1153;i-Pr,i-Pr,i-Pr],[RY1154;i-Pr,i-Pr,c-Pr],[RY1155;i-Pr,i-Pr,t-Bu],[RY1156;i-Pr,i-Pr,Bu],[RY1157;i-Pr,i-Pr,t-Bu],[RY1158;i-Pr,i-Pr,c-PrCH2],[RY1159;i-Pr,i-Pr,Ph],[RY1160;i-Pr,i-Pr,Bn],[RY1161;i-Pr,i-Pr,CF3],[RY1162;i-Pr,i-Pr,CF3CH2],[RY1163;i-Pr,i-Pr,CF3CF2],[RY1164;i-Pr,i-Pr,CF2H],[RY1165;i-Pr,i-Pr,CF2HCH2],[RY1166;c-Pr,i-Pr,i-Pr],[RY1167;c-Pr,i-Pr,c-Pr],[RY1168;c-Pr,i-Pr,t-Bu],[RY1169;c-Pr,i-Pr,Bu],[RY1170;c-Pr,i-Pr,t-Bu],[RY1171;c-Pr,i-Pr,c-PrCH2],[RY1172;c-Pr,i-Pr,Ph],[RY1173;c-Pr,i-Pr,Bn],[RY1174;c-Pr,i-Pr,CF3],[RY1175;c-Pr,i-Pr,CF3CH2],[RY1176;c-Pr,i-Pr,CF3CF2],[RY1177;c-Pr,i-Pr,CF2H],[RY1178;c-Pr,i-Pr,CF2HCH2],[RY1179;c-PrCH2,i-Pr,i-Pr],[RY1180;c-PrCH2,i-Pr,c-Pr],[RY1181;c-PrCH2,i-Pr,t-Bu],[RY1182;c-PrCH2,i-Pr,Bu],[RY1183;c-PrCH2,i-Pr,t-Bu],[RY1184;c-PrCH2,i-Pr,c-PrCH2],[RY1185;c-PrCH2,i-Pr,Ph],[RY1186;c-PrCH2,i-Pr,Bn],[RY1187;c-PrCH2,i-Pr,CF3],[RY1188;c-PrCH2,i-Pr,CF3CH2],[RY1189;c-PrCH2,i-Pr,CF3CF2],[RY1190;c-PrCH2,i-Pr,CF2H],[RY1191;c-PrCH2,i-Pr,CF2HCH2],[RY1192;i-Bu,i-Pr,i-Pr],[RY1193;i-Bu,i-Pr,c-Pr],[RY1194;i-Bu,i-Pr,t-Bu],[RY1195;i-Bu,i-Pr,Bu],[RY1196;i-Bu,i-Pr,t-Bu],[RY1197;i-Bu,i-Pr,c-PrCH2],[RY1198;i-Bu,i-Pr,Ph],[RY1199;i-Bu,i-Pr,Bn],[RY1200;i-Bu,i-Pr,CF3], [RY1001; MeOCH 2, Pr, CF 2 H], [RY1002; MeOCH 2, Pr, CF 2 HCH 2], [RY1003; EtOCH 2, Pr, Pr], [RY1004; EtOCH 2, Pr, i-Pr] , [RY1005; EtOCH 2, Pr , c-Pr], [RY1006; EtOCH 2, Pr, t-Bu], [RY1007; EtOCH 2, Pr, Bu], [RY1008; EtOCH 2, Pr, t-Bu] , [RY1009; EtOCH 2, Pr , c-PrCH 2], [RY1010; EtOCH 2, Pr, Ph], [RY1011; EtOCH 2, Pr, Bn], [RY1012; EtOCH 2, Pr, CF 3], [ RY1013; EtOCH 2, Pr, CF 3 CH 2], [RY1014; EtOCH 2, Pr, CF 3 CF 2], [RY1015; EtOCH 2, Pr, CF 2 H], [RY1016; EtOCH 2, Pr, CF 2 HCH 2], [RY1017; MeSCH 2, Pr, Pr], [RY1018; MeSCH 2, Pr, i-Pr], [RY1019; MeSCH 2, Pr, c-Pr], [RY1020; MeSCH 2, Pr, t -Bu], [RY1021; MeSCH 2 , Pr, Bu], [RY1022; MeSCH 2, Pr, t-Bu], [RY1023; MeSCH 2, Pr, c-PrCH 2], [RY1024; MeSCH 2, Pr, Ph], [RY1025; MeSCH 2 , Pr, Bn], [RY1026; MeSCH 2, Pr, CF 3], [RY1027; MeSCH 2, Pr, CF 3 CH 2], [RY1028; MeSCH 2, Pr, CF 3 CF 2], [RY1029; MeSCH 2, Pr, CF 2 H], [RY1030; MeSCH 2, Pr, CF 2 HCH 2], [RY1031; EtSCH 2, Pr, Pr], [RY1032; EtSCH 2, Pr, i-Pr], [RY1033; EtSCH 2, Pr, c-Pr], [RY1034; EtSCH 2, Pr, t-Bu], [RY1035; EtSCH 2, Pr, Bu], [RY1036; EtSCH 2, Pr, t-Bu], [RY1037; EtSCH 2 , Pr, c -PrCH 2], [RY1038; EtSCH 2, Pr, Ph], [RY1039; EtSCH 2, Pr, Bn], [RY1040; EtSCH 2, Pr, CF 3], [RY1041; EtSCH 2, Pr, CF 3 CH 2], [RY1042; EtSCH 2 , Pr, CF 3 CF 2], [RY1043; EtSCH 2, Pr, CF 2 H], [RY1044; EtSCH 2, Pr, CF 2 HCH 2], [RY1045; Ph, Pr , Pr], [RY1046; Ph, Pr, i-Pr], [RY1047; Ph, Pr, c-Pr], [RY1048; Ph, Pr, t-Bu], [RY1049; Ph, Pr, Bu], [RY1050; Ph, Pr, t -Bu], [RY1051; Ph, Pr, c-PrCH 2], [RY1052; Ph, Pr, Ph], [RY1053; Ph, Pr, Bn], [RY1054; Ph, Pr, CF 3], [RY1055 ; Ph, Pr, CF 3 CH 2], [RY1056; Ph, Pr, CF 3 CF 2], [RY1057; Ph, Pr, CF 2 H], [RY1058; Ph, Pr , CF 2 HCH 2], [ RY1059; Bn, Pr, Pr], [RY1060; Bn, Pr, i-Pr], [RY1061; Bn, Pr, c-Pr], [RY1062; Bn, Pr, t- Bu], [RY1063; Bn, Pr, Bu], [RY1064; Bn, Pr, t-Bu], [RY1065; Bn, Pr, c-PrCH 2], [RY1066; Bn, Pr, Ph], [RY1067 ; Bn, Pr, Bn], [RY1068; Bn, Pr, CF 3], [RY1069; Bn, Pr, CF 3 CH 2], [RY1070; Bn, Pr, CF 3 CF 2], [RY1071; Bn, Pr, CF 2 H], [ RY1072; Bn, Pr, CF 2 HCH 2], [RY1073; HCCCH 2, Pr, Pr], [RY1074; HCCCH 2, Pr, i-Pr], [RY1075; HCCCH 2, Pr, c-Pr], [ RY1076; HCCCH 2, Pr, t-Bu], [RY1077; HCCCH 2, Pr, Bu], [RY1078; HCCCH 2, Pr, t-Bu], [RY1079; HCCCH 2, Pr, c-PrCH 2 ], [RY 1080; H CCCH 2, Pr, Ph], [RY1081; HCCCH 2, Pr, Bn], [RY1082; HCCCH 2, Pr, CF 3], [RY1083; HCCCH 2, Pr, CF 3 CH 2], [RY1084; HCCCH 2 , Pr, CF 3 CF 2] , [RY1085; HCCCH 2, Pr, CF 2 H], [RY1086; HCCCH 2, Pr, CF 2 HCH 2], [RY1087; CH 3 CCCH 2, Pr, Pr], [ RY1088; CH 3 CCCH 2, Pr , i-Pr], [RY1089; CH 3 CCCH 2, Pr, c-Pr], [RY1090; CH 3 CCCH 2, Pr, t-Bu], [RY1091; CH 3 CCCH 2, Pr, Bu], [ RY1092; CH 3 CCCH 2, Pr, t-Bu], [RY1093; CH 3 CCCH 2, Pr, c-PrCH 2], [RY1094; CH 3 CCCH 2, Pr, Ph] , [RY1095; CH 3 CCCH 2 , Pr, Bn], [RY1096; CH 3 CCCH 2, Pr, CF 3], [RY1097; CH 3 CCCH 2, Pr, CF 3 CH 2], [RY1098; CH 3 CCCH 2, Pr, CF 3 CF 2 ], [RY1099; CH 3 CCCH 2, Pr, CF 2 H], [RY1100; CH 3 CCCH 2, Pr, CF 2 HCH 2], [RY1101; H, i-Pr, i-Pr], [RY 1102; H, i-Pr, c-Pr], [RY 1103; H, i-Pr, t-Bu], [RY 1104; H, i-Pr, Bu], [RY 1 105; H, i-Pr, t-Bu], [RY 1106; H, i-Pr, c-PrCH 2 ], [RY 1107; H, i-Pr, Ph], [RY 1108; H, i-Pr, Bn], [RY 1109 H, i-Pr, CF 3 ], [RY 1110; H, i-Pr, CF 3 CH 2 ], [RY 1111; H, i-Pr, CF 3 CF 2 ], [RY 1112; H, i-Pr, CF 2 H], [RY1113; H, i-Pr, CF 2 HCH 2], [RY1114; Me, i-Pr, i-Pr], [RY1115; Me, i-Pr, c-Pr], [RY1116 Me, i-Pr, t-Bu], [RY 1117; Me , i-Pr, Bu], [RY 1118; Me, i-Pr, t-Bu], [RY 1119; Me, i-Pr, c-PrCH 2 ], [RY 1 120; Me, i-Pr, Ph], [RY 1 120; RY1121; Me, i-Pr, Bn], [RY1122; Me, i-Pr, CF 3], [RY1123; Me, i-Pr, CF 3 CH 2], [RY1124; Me, i-Pr, CF 3 CF 2 ], [RY 1125; Me, i-Pr, CF 2 H], [RY 1 126; Me, i-Pr, CF 2 HCH 2 ], [RY 1127; Et, i-Pr, i-Pr], [RY 1 128; Et, i-Pr, c-Pr], [RY 1129; Et, i-Pr, t-Bu], [RY 1130; Et, i-Pr, Bu], [RY 1131; Et, i-Pr, t-Bu] , [RY 1132; Et, i-Pr, c-PrCH 2 ], [RY 1 133; Et, i-Pr, Ph], [RY 1 134; Et, i-Pr, Bn], [RY 1 135; Et, i-Pr, CF 3], [RY1136; Et, i-Pr, CF 3 CH 2], [RY1137; Et, i-Pr, CF 3 CF 2], [RY1138; Et, i-Pr, CF 2 H], [RY1139; Et, i-Pr, CF 2 HCH 2], [RY1140; Pr, i-Pr, i-Pr], [RY1141; Pr, i-Pr, c-Pr], [RY1142; Pr, i-Pr, t -Bu], [RY1143; Pr, i-Pr, Bu], [RY 1144; Pr, i-Pr, t-Bu], [RY 1145; Pr, i-Pr, c-PrCH 2 ], [RY 1146; Pr, i-Pr, Ph], [RY 1147; Pr, i-Pr, Bn], [RY 1148; Pr, i-Pr, CF 3 ], [RY 1149; Pr, i-Pr, CF 3 CH 2 ], [RY 1 150; Pr, i-Pr, CF 3 CF 2], [RY1151; Pr, i-Pr, CF 2 H], [RY1152; Pr, i-Pr, CF 2 HCH 2], [RY1153; i-Pr, i- Pr, i-Pr], [RY1154; i-Pr, i-Pr, c-Pr], [RY1155; i-Pr, i-Pr, t-Bu], [RY1156; i-Pr, i-Pr, Bu], [RY 1157; i-Pr, i-Pr, t-Bu], [RY 1158; i-Pr, i-Pr, c-PrCH 2 ], [RY 1 159; i-Pr, i-Pr, Ph], [RY1160; i-Pr, i-Pr, Bn], [RY1161; i-Pr, i-Pr, CF 3 ], [RY1162; i-Pr, i-Pr , CF 3 CH 2 ], [RY 1163; i-Pr, i-Pr, CF 3 CF 2 ], [RY 1164; i-Pr, i-Pr, CF 2 H], [RY 1165; i-Pr, i-Pr , CF 2 HCH 2 ], [RY 1166; c-Pr, i-Pr, i-Pr], [RY 1167; c-Pr, i-Pr, c-Pr], [RY 1 168; c-Pr, i-Pr, t-Bu], [RY 1169; c-Pr, i-Pr, Bu], [RY 1170; c-Pr, i-Pr, t-Bu], [RY 1171; c-Pr, i-Pr, c-PrCH 2 ], [RY1172; c-Pr , i-Pr, Ph], [RY1173; c-Pr, i-Pr, Bn], [RY1174; c-Pr, i-Pr, CF 3], [RY1175; c- Pr, i-Pr, CF 3 CH 2], [RY1176; c-Pr, i-Pr, CF 3 CF 2], [RY1177; c-Pr, i-Pr, CF 2 H], [RY1178; c- Pr, i-Pr, CF 2 HCH 2], [RY1179; c-PrCH 2, i-Pr, i-Pr], [RY1180; c-PrCH 2, i-Pr, c-Pr], [RY1181; c -PrCH 2, i-Pr, t -Bu], [RY1182; c-PrCH 2, i-Pr, Bu], [RY1183; c-PrCH 2, i-Pr, t-Bu], [RY1184; c- PrCH 2 , i-Pr, c-PrCH 2 ], [RY 1185; c-PrCH 2 , i-Pr, Ph], [RY 1186; c-PrCH 2 , i-Pr, Bn], [RY 1187; c-PrCH 2 , i-Pr, CF 3 ], [RY 1188; c-PrCH 2 , i-Pr, CF 3 CH 2 ], [RY 1189; c-PrCH 2 , i-Pr, CF 3 CF 2 ], [RY 1190; c- PrCH 2, i-Pr, CF 2 H], [RY1191; c-PrCH 2, i-Pr, CF 2 HCH 2], [RY1192; i-Bu, i-Pr, i-Pr], [RY1193; i -Bu, i-Pr, c-Pr], [RY 1194; i-Bu, i-Pr, t-Bu], [RY 1195; i-Bu, i-Pr, B u], [RY 1196; i-Bu, i-Pr, t-Bu], [RY 1197; i-Bu, i-Pr, c-PrCH 2 ], [RY 1198; i-Bu, i-Pr, Ph], [RY 1199; i-Bu, i-Pr, Bn], [RY 1200; i-Bu, i-Pr, CF 3 ],

[RY1201;i-Bu,i-Pr,CF3CH2],[RY1202;i-Bu,i-Pr,CF3CF2],[RY1203;i-Bu,i-Pr,CF2H],[RY1204;i-Bu,i-Pr,CF2HCH2],[RY1205;CF3CH2,i-Pr,i-Pr],[RY1206;CF3CH2,i-Pr,c-Pr],[RY1207;CF3CH2,i-Pr,t-Bu],[RY1208;CF3CH2,i-Pr,Bu],[RY1209;CF3CH2,i-Pr,t-Bu],[RY1210;CF3CH2,i-Pr,c-PrCH2],[RY1211;CF3CH2,i-Pr,Ph],[RY1212;CF3CH2,i-Pr,Bn],[RY1213;CF3CH2,i-Pr,CF3],[RY1214;CF3CH2,i-Pr,CF3CH2],[RY1215;CF3CH2,i-Pr,CF3CF2],[RY1216;CF3CH2,i-Pr,CF2H],[RY1217;CF3CH2,i-Pr,CF2HCH2],[RY1218;CF2HCH2,i-Pr,i-Pr],[RY1219;CF2HCH2,i-Pr,c-Pr],[RY1220;CF2HCH2,i-Pr,t-Bu],[RY1221;CF2HCH2,i-Pr,Bu],[RY1222;CF2HCH2,i-Pr,t-Bu],[RY1223;CF2HCH2,i-Pr,c-PrCH2],[RY1224;CF2HCH2,i-Pr,Ph],[RY1225;CF2HCH2,i-Pr,Bn],[RY1226;CF2HCH2,i-Pr,CF3],[RY1227;CF2HCH2,i-Pr,CF3CH2],[RY1228;CF2HCH2,i-Pr,CF3CF2],[RY1229;CF2HCH2,i-Pr,CF2H],[RY1230;CF2HCH2,i-Pr,CF2HCH2],[RY1231;MeOCH2,i-Pr,i-Pr],[RY1232;MeOCH2,i-Pr,c-Pr],[RY1233;MeOCH2,i-Pr,t-Bu],[RY1234;MeOCH2,i-Pr,Bu],[RY1235;MeOCH2,i-Pr,t-Bu],[RY1236;MeOCH2,i-Pr,c-PrCH2],[RY1237;MeOCH2,i-Pr,Ph],[RY1238;MeOCH2,i-Pr,Bn],[RY1239;MeOCH2,i-Pr,CF3],[RY1240;MeOCH2,i-Pr,CF3CH2],[RY1241;MeOCH2,i-Pr,CF3CF2],[RY1242;MeOCH2,i-Pr,CF2H],[RY1243;MeOCH2,i-Pr,CF2HCH2],[RY1244;EtOCH2,i-Pr,i-Pr],[RY1245;EtOCH2,i-Pr,c-Pr],[RY1246;EtOCH2,i-Pr,t-Bu],[RY1247;EtOCH2,i-Pr,Bu],[RY1248;EtOCH2,i-Pr,t-Bu],[RY1249;EtOCH2,i-Pr,c-PrCH2],[RY1250;EtOCH2,i-Pr,Ph],[RY1251;EtOCH2,i-Pr,Bn],[RY1252;EtOCH2,i-Pr,CF3],[RY1253;EtOCH2,i-Pr,CF3CH2],[RY1254;EtOCH2,i-Pr,CF3CF2],[RY1255;EtOCH2,i-Pr,CF2H],[RY1256;EtOCH2,i-Pr,CF2HCH2],[RY1257;MeSCH2,i-Pr,i-Pr],[RY1258;MeSCH2,i-Pr,c-Pr],[RY1259;MeSCH2,i-Pr,t-Bu],[RY1260;MeSCH2,i-Pr,Bu],[RY1261;MeSCH2,i-Pr,t-Bu],[RY1262;MeSCH2,i-Pr,c-PrCH2],[RY1263;MeSCH2,i-Pr,Ph],[RY1264;MeSCH2,i-Pr,Bn],[RY1265;MeSCH2,i-Pr,CF3],[RY1266;MeSCH2,i-Pr,CF3CH2],[RY1267;MeSCH2,i-Pr,CF3CF2],[RY1268;MeSCH2,i-Pr,CF2H],[RY1269;MeSCH2,i-Pr,CF2HCH2],[RY1270;EtSCH2,i-Pr,i-Pr],[RY1271;EtSCH2,i-Pr,c-Pr],[RY1272;EtSCH2,i-Pr,t-Bu],[RY1273;EtSCH2,i-Pr,Bu],[RY1274;EtSCH2,i-Pr,t-Bu],[RY1275;EtSCH2,i-Pr,c-PrCH2],[RY1276;EtSCH2,i-Pr,Ph],[RY1277;EtSCH2,i-Pr,Bn],[RY1278;EtSCH2,i-Pr,CF3],[RY1279;EtSCH2,i-Pr,CF3CH2],[RY1280;EtSCH2,i-Pr,CF3CF2],[RY1281;EtSCH2,i-Pr,CF2H],[RY1282;EtSCH2,i-Pr,CF2HCH2],[RY1283;Ph,i-Pr,i-Pr],[RY1284;Ph,i-Pr,c-Pr],[RY1285;Ph,i-Pr,t-Bu],[RY1286;Ph,i-Pr,Bu],[RY1287;Ph,i-Pr,t-Bu],[RY1288;Ph,i-Pr,c-PrCH2],[RY1289;Ph,i-Pr,Ph],[RY1290;Ph,i-Pr,Bn],[RY1291;Ph,i-Pr,CF3],[RY1292;Ph,i-Pr,CF3CH2],[RY1293;Ph,i-Pr,CF3CF2],[RY1294;Ph,i-Pr,CF2H],[RY1295;Ph,i-Pr,CF2HCH2],[RY1296;Bn,i-Pr,i-Pr],[RY1297;Bn,i-Pr,c-Pr],[RY1298;Bn,i-Pr,t-Bu],[RY1299;Bn,i-Pr,Bu],[RY1300;Bn,i-Pr,t-Bu],[RY1301;Bn,i-Pr,c-PrCH2],[RY1302;Bn,i-Pr,Ph],[RY1303;Bn,i-Pr,Bn],[RY1304;Bn,i-Pr,CF3],[RY1305;Bn,i-Pr,CF3CH2],[RY1306;Bn,i-Pr,CF3CF2],[RY1307;Bn,i-Pr,CF2H],[RY1308;Bn,i-Pr,CF2HCH2],[RY1309;HCCCH2,i-Pr,i-Pr],[RY1310;HCCCH2,i-Pr,c-Pr],[RY1311;HCCCH2,i-Pr,t-Bu],[RY1312;HCCCH2,i-Pr,Bu],[RY1313;HCCCH2,i-Pr,t-Bu],[RY1314;HCCCH2,i-Pr,c-PrCH2],[RY1315;HCCCH2,i-Pr,Ph],[RY1316;HCCCH2,i-Pr,Bn],[RY1317;HCCCH2,i-Pr,CF3],[RY1318;HCCCH2,i-Pr,CF3CH2],[RY1319;HCCCH2,i-Pr,CF3CF2],[RY1320;HCCCH2,i-Pr,CF2H],[RY1321;HCCCH2,i-Pr,CF2HCH2],[RY1322;CH3CCCH2,i-Pr,i-Pr],[RY1323;CH3CCCH2,i-Pr,c-Pr],[RY1324;CH3CCCH2,i-Pr,t-Bu],[RY1325;CH3CCCH2,i-Pr,Bu],[RY1326;CH3CCCH2,i-Pr,t-Bu],[RY1327;CH3CCCH2,i-Pr,c-PrCH2],[RY1328;CH3CCCH2,i-Pr,Ph],[RY1329;CH3CCCH2,i-Pr,Bn],[RY1330;CH3CCCH2,i-Pr,CF3],[RY1331;CH3CCCH2,i-Pr,CF3CH2],[RY1332;CH3CCCH2,i-Pr,CF3CF2],[RY1333;CH3CCCH2,i-Pr,CF2H],[RY1334;CH3CCCH2,i-Pr,CF2HCH2],[RY1335;H,c-Pr,c-Pr],[RY1336;H,c-Pr,t-Bu],[RY1337;H,c-Pr,Bu],[RY1338;H,c-Pr,t-Bu],[RY1339;H,c-Pr,c-PrCH2],[RY1340;H,c-Pr,Ph],[RY1341;H,c-Pr,Bn],[RY1342;H,c-Pr,CF3],[RY1343;H,c-Pr,CF3CH2],[RY1344;H,c-Pr,CF3CF2],[RY1345;H,c-Pr,CF2H],[RY1346;H,c-Pr,CF2HCH2],[RY1347;Me,c-Pr,c-Pr],[RY1348;Me,c-Pr,t-Bu],[RY1349;Me,c-Pr,Bu],[RY1350;Me,c-Pr,t-Bu],[RY1351;Me,c-Pr,c-PrCH2],[RY1352;Me,c-Pr,Ph],[RY1353;Me,c-Pr,Bn],[RY1354;Me,c-Pr,CF3],[RY1355;Me,c-Pr,CF3CH2],[RY1356;Me,c-Pr,CF3CF2],[RY1357;Me,c-Pr,CF2H],[RY1358;Me,c-Pr,CF2HCH2],[RY1359;Et,c-Pr,c-Pr],[RY1360;Et,c-Pr,t-Bu],[RY1361;Et,c-Pr,Bu],[RY1362;Et,c-Pr,t-Bu],[RY1363;Et,c-Pr,c-PrCH2],[RY1364;Et,c-Pr,Ph],[RY1365;Et,c-Pr,Bn],[RY1366;Et,c-Pr,CF3],[RY1367;Et,c-Pr,CF3CH2],[RY1368;Et,c-Pr,CF3CF2],[RY1369;Et,c-Pr,CF2H],[RY1370;Et,c-Pr,CF2HCH2],[RY1371;Pr,c-Pr,c-Pr],[RY1372;Pr,c-Pr,t-Bu],[RY1373;Pr,c-Pr,Bu],[RY1374;Pr,c-Pr,t-Bu],[RY1375;Pr,c-Pr,c-PrCH2],[RY1376;Pr,c-Pr,Ph],[RY1377;Pr,c-Pr,Bn],[RY1378;Pr,c-Pr,CF3],[RY1379;Pr,c-Pr,CF3CH2],[RY1380;Pr,c-Pr,CF3CF2],[RY1381;Pr,c-Pr,CF2H],[RY1382;Pr,c-Pr,CF2HCH2],[RY1383;i-Pr,c-Pr,c-Pr],[RY1384;i-Pr,c-Pr,t-Bu],[RY1385;i-Pr,c-Pr,Bu],[RY1386;i-Pr,c-Pr,t-Bu],[RY1387;i-Pr,c-Pr,c-PrCH2],[RY1388;i-Pr,c-Pr,Ph],[RY1389;i-Pr,c-Pr,Bn],[RY1390;i-Pr,c-Pr,CF3],[RY1391;i-Pr,c-Pr,CF3CH2],[RY1392;i-Pr,c-Pr,CF3CF2],[RY1393;i-Pr,c-Pr,CF2H],[RY1394;i-Pr,c-Pr,CF2HCH2],[RY1395;c-Pr,c-Pr,c-Pr],[RY1396;c-Pr,c-Pr,t-Bu],[RY1397;c-Pr,c-Pr,Bu],[RY1398;c-Pr,c-Pr,t-Bu],[RY1399;c-Pr,c-Pr,c-PrCH2],[RY1400;c-Pr,c-Pr,Ph], [RY1201; i-Bu, i -Pr, CF 3 CH 2], [RY1202; i-Bu, i-Pr, CF 3 CF 2], [RY1203; i-Bu, i-Pr, CF 2 H], [RY 1204; i-Bu, i-Pr, CF 2 HCH 2 ], [RY 1205; CF 3 CH 2 , i-Pr, i-Pr], [RY 1206; CF 3 CH 2 , i-Pr, c-Pr] , [RY1207; CF 3 CH 2 , i-Pr, t-Bu], [RY1208; CF 3 CH 2, i-Pr, Bu], [RY1209; CF 3 CH 2, i-Pr, t-Bu], [RY1210; CF 3 CH 2, i-Pr, c-PrCH 2], [RY1211; CF 3 CH 2, i-Pr, Ph], [RY1212; CF 3 CH 2, i-Pr, Bn], [RY1213 CF 3 CH 2 , i-Pr, CF 3 ], [RY 1214; CF 3 CH 2 , i-Pr, CF 3 CH 2 ], [RY 1215; CF 3 CH 2 , i-Pr, CF 3 CF 2 ], [RY1216; CF 3 CH 2, i-Pr, CF 2 H], [RY1217; CF 3 CH 2, i-Pr, CF 2 HCH 2], [RY1218; CF 2 HCH 2, i-Pr, i-Pr ], [RY1219; CF 2 HCH 2, i-Pr, c-Pr], [RY1220; CF 2 HCH 2, i-Pr, t-Bu], [RY1221; CF 2 HCH 2, i-Pr, Bu] , [RY1222; CF 2 HCH 2 , i-Pr, t-Bu], [RY1223; CF 2 HCH 2, i-Pr, c-PrCH 2], [RY1224; CF 2 HCH 2, i-Pr, Ph] , [RY1225; CF 2 HCH 2 , i-Pr, Bn], [RY1226; CF 2 HCH 2, i-Pr, CF 3], [RY1227; CF 2 HCH 2, i-Pr, CF 3 CH 2], [RY1228; CF 2 HCH 2, i-Pr, CF 3 CF 2], [RY1229; CF 2 HCH 2, i-Pr, CF 2 H], [RY1230; CF 2 HCH 2, i-Pr, CF 2 HCH 2], [RY1231; MeOCH 2 , i-Pr, i-Pr], [RY1232; MeOCH 2, i-P r, c-Pr], [ RY1233; MeOCH 2, i-Pr, t-Bu], [RY1234; MeOCH 2, i-Pr, Bu], [RY1235; MeOCH 2, i-Pr, t-Bu], [RY1236; MeOCH 2, i- Pr, c-PrCH 2], [RY1237; MeOCH 2, i-Pr, Ph], [RY1238; MeOCH 2, i-Pr, Bn], [RY1239; MeOCH 2, i- Pr, CF 3 ], [RY 1240; MeOCH 2 , i-Pr, CF 3 CH 2 ], [RY 1241; MeOCH 2 , i-Pr, CF 3 CF 2 ], [RY 1242; MeOCH 2 , i-Pr, CF 2 H], [RY1243; MeOCH 2 , i-Pr, CF 2 HCH 2], [RY1244; EtOCH 2, i-Pr, i-Pr], [RY1245; EtOCH 2, i-Pr, c-Pr], [ RY 1246; EtOCH 2 , i-Pr, t-Bu], [RY 1247; EtOCH 2 , i-Pr, Bu], [RY 1248; EtOCH 2 , i-Pr, t-Bu], [RY 1249; EtOCH 2 , i- Pr, c-PrCH 2], [RY1250; EtOCH 2, i-Pr, Ph], [RY1251; EtOCH 2, i-Pr, Bn], [RY1252; EtOCH 2, i-Pr, CF 3], [RY1253 EtOCH 2 , i-Pr, CF 3 CH 2 ], [RY 1254; EtOCH 2 , i-Pr, CF 3 CF 2 ], [RY 1 255; EtOCH 2 , i-Pr, CF 2 H], [RY 1 256; EtOCH 2 , i-Pr, CF 2 HCH 2], [RY1257; MeSCH 2, i-Pr, i-Pr], [RY1258; MeSCH 2, i-Pr, c-Pr], [RY1259; MeSCH 2, i-Pr , t-Bu], [RY 1260; MeSCH 2 , i-Pr, Bu], [RY 1261; MeSCH 2 , i-Pr, t-Bu], [RY 1262; MeSCH 2 , i-Pr, c-PrCH 2 ], [RY 1263; MeSCH 2 , i-Pr, Ph], [RY 1264; MeSCH 2 , i-Pr, Bn], [RY 1265; MeSCH 2 , i-Pr, CF 3 ], [RY 1266; MeSCH 2 , i-Pr, CF 3 CH 2], [RY1267; MeSCH 2, i-Pr, CF 3 CF 2], [RY1268; MeSCH 2, i-Pr, CF 2 H], [RY1269; MeSCH 2, i-Pr, CF 2 HCH 2] , [RY 1270; EtSCH 2 , i-Pr, i-Pr], [RY 1271; EtSCH 2 , i-Pr, c-Pr], [RY 1272; EtSCH 2 , i-Pr, t-Bu], [RY 1273; EtSCH 2, i-Pr, Bu] , [RY1274; EtSCH 2, i-Pr, t-Bu], [RY1275; EtSCH 2, i-Pr, c-PrCH 2], [RY1276; EtSCH 2, i-Pr, Ph], [RY1277; EtSCH 2 , i-Pr, Bn], [RY1278; EtSCH 2, i-Pr, CF 3], [RY1279; EtSCH 2, i-Pr, CF 3 CH 2], [RY1280; EtSCH 2, i-Pr, CF 3 CF 2], [RY1281; EtSCH 2, i-Pr, CF 2 H], [RY1282; EtSCH 2, i-Pr, CF 2 HCH 2], [RY1283; Ph, i- Pr, i-Pr], [RY1284; Ph, i-Pr, c-Pr], [RY1285; Ph, i-Pr, t-Bu], [RY1286; Ph, i-Pr, Bu], [RY1287; Ph, i-Pr, t-Bu], [RY 1 288; Ph, i-Pr, c-PrCH 2 ], [RY 1 289; Ph, i-Pr, Ph], [RY 1290; Ph, i-Pr, Bn], [RY1291; Ph, i-Pr , CF 3], [RY1292; Ph, i-Pr, CF 3 CH 2], [RY1293; Ph, i-Pr, CF 3 CF 2], [RY1294; Ph, i- Pr, CF 2 H], [ RY1295; Ph, i-Pr, CF 2 HCH 2], [RY1296; Bn, i-Pr, i-Pr], [RY1297; Bn, i-Pr, c-Pr], [RY1298; Bn, i-Pr, t-Bu], [RY 1299; Bn, i-Pr, Bu], [RY 1300; Bn, i-Pr, t-Bu], [RY1301; Bn, i-Pr, c -PrCH 2], [RY1302; Bn , i-Pr, Ph], [RY1303; Bn, i-Pr, Bn], [RY1304; Bn, i-Pr, CF 3], [RY 1305; Bn, i-Pr, CF 3 CH 2], [RY1306; Bn, i-Pr, CF 3 CF 2], [RY1307; Bn, i-Pr, CF 2 H], [RY1308; Bn, i- Pr, CF 2 HCH 2], [RY1309; HCCCH 2, i-Pr, i-Pr], [RY1310; HCCCH 2, i-Pr, c-Pr], [RY1311; HCCCH 2, i-Pr, t- Bu], [RY1312; HCCCH 2 , i-Pr, Bu], [RY1313; HCCCH 2, i-Pr, t-Bu], [RY1314; HCCCH 2, i-Pr, c-PrCH 2], [RY1315; HCCCH 2, i-Pr, Ph ], [RY1316; HCCCH 2, i-Pr, Bn], [RY1317; HCCCH 2, i-Pr, CF 3], [RY1318; HCCCH 2, i-Pr, CF 3 CH 2], [RY1319; HCCCH 2 , i-Pr, CF 3 CF 2], [RY1320; HCCCH 2, i-Pr, CF 2 H], [RY1321; HCCCH 2, i-Pr, CF 2 HCH 2], [RY1322; CH 3 CCCH 2, i-Pr, i-Pr], [RY1323; CH 3 CCCH 2, i-Pr, c-Pr], [RY1324; CH 3 CCCH 2, i-Pr, t-Bu] , [RY 1325; CH 3 CCCH 2 , i-Pr, Bu], [RY 1326; CH 3 CCCH 2 , i-Pr, t-Bu], [RY 1327; CH 3 CCCH 2 , i-Pr, c-PrCH 2 ] , [RY1328; CH 3 CCCH 2 , i-Pr, Ph], [RY1329; CH 3 CCCH 2, i-Pr, Bn], [RY1330; CH 3 CCCH 2, i-Pr, CF 3], [RY1331; CH 3 CCCH 2, i-Pr , CF 3 CH 2], [RY1332; CH 3 CCCH 2, i-Pr, CF 3 CF 2], [RY1333; CH 3 CCCH 2, i-Pr, CF 2 H], [RY1334; CH 3 CCCH 2, i-Pr, CF 2 HCH 2], [RY1335; H, c-Pr, c-Pr], [RY1336; H, c-Pr, t-Bu], [RY1337; H , c-Pr, Bu], [RY 1338; H, c -Pr, t-Bu], [ RY1339; H, c-Pr, c-PrCH 2], [RY1340; H, c-Pr, Ph], [RY1341; H, c-Pr, Bn], [RY1342; H, c-Pr, CF 3 ], [RY1343; H, c-Pr, CF 3 CH 2], [RY1344; H, c-Pr, CF 3 CF 2], [RY1345; H, c-Pr, CF 2 H], [RY 1346; H, c-Pr, CF 2 HCH 2 ], [RY 1347; Me, c-Pr, c-Pr], [RY 1348; Me, c-Pr, t-Bu], [RY 1 349; Me, c-Pr, Bu], [RY 1350; Me, c-Pr, t-Bu], [RY 1351; Me, c-Pr, c-PrCH 2 ], [RY 1352; Me, c-Pr, Ph], [RY1353; Me, c-Pr , Bn], [RY1354; Me, c-Pr, CF 3], [RY1355; Me, c-Pr, CF 3 CH 2], [RY1356; Me, c-Pr, CF 3 CF 2 ], [RY 1357; Me, c-Pr, CF 2 H], [RY 1358; Me, c-Pr, CF 2 HCH 2 ], [RY 1359; Et, c-Pr, c-Pr], [RY 1 360 Et, c-Pr, t-Bu], [RY1361; Et, c-Pr, Bu], [RY1362; Et, c-Pr, t-Bu], [RY1363; Et, c-Pr, c-PrCH 2 ], [RY 1364; Et, c-Pr, Ph], [RY 1365; Et, c-Pr, Bn], [RY 1366; Et, c-Pr, CF 3 ], [RY 1367; Et, c-Pr, CF 3 CH 2 ], [RY 1368; Et, c-Pr, CF 3 CF 2 ], [RY 1369; Et, c-Pr, CF 2 H], [RY 1370; Et, c-Pr, CF 2 HCH 2 ], [[ RY1371; Pr, c-Pr, c-Pr], [RY1372; Pr, c-Pr, t-Bu], [RY1373; Pr, c-Pr, Bu], [RY 1374; Pr, c-Pr, t- Bu], [RY 1375; Pr, c-Pr, c-PrCH 2 ], [RY 1376; Pr, c-Pr, Ph], [RY 1377; Pr, c-Pr, Bn], [RY 1378; Pr, c-Pr , CF 3 ], [RY 1379; Pr, c-Pr, CF 3 CH 2 ], [RY 1380; Pr, c-Pr, CF 3 CF 2 ], [RY1381; Pr, c -Pr, CF 2 H], [RY1382; Pr, c-Pr, CF 2 HCH 2], [RY1383; i-Pr, c-Pr, c-Pr], [RY1384; i-Pr, c-Pr, t-Bu], [RY 1385; i-Pr, c-Pr, Bu], [RY 1386; i-Pr, c-Pr, t-Bu], [RY 1387; i-Pr, c-Pr, c-PrCH 2 ], [RY 1388; i-Pr, c-Pr, Ph], [RY 1389; i-Pr, c-Pr, Bn], [RY 1390; i-Pr, c-Pr, CF 3], [RY1391; i- Pr, c-Pr, CF 3 CH 2], [RY1392; i-Pr, c-Pr, CF 3 CF 2], [RY1393; i-Pr, c-Pr, CF 2 H], [RY1394; i-Pr, c-Pr, CF 2 HCH 2 ], [RY 1395; c-Pr, c-Pr, c-Pr], [RY 1396; c-Pr, c-Pr, t-Bu ], [RY 1397; c-Pr, c-Pr, Bu], [RY 1398; c-Pr, c-Pr, t-Bu], [RY 1399; c-Pr, c-Pr, c-PrCH 2 ], [[ RY 1400; c-Pr, c-Pr, Ph],

[RY1401;c-Pr,c-Pr,Bn],[RY1402;c-Pr,c-Pr,CF3],[RY1403;c-Pr,c-Pr,CF3CH2],[RY1404;c-Pr,c-Pr,CF3CF2],[RY1405;c-Pr,c-Pr,CF2H],[RY1406;c-Pr,c-Pr,CF2HCH2],[RY1407;c-PrCH2,c-Pr,c-Pr],[RY1408;c-PrCH2,c-Pr,t-Bu],[RY1409;c-PrCH2,c-Pr,Bu],[RY1410;c-PrCH2,c-Pr,t-Bu],[RY1411;c-PrCH2,c-Pr,c-PrCH2],[RY1412;c-PrCH2,c-Pr,Ph],[RY1413;c-PrCH2,c-Pr,Bn],[RY1414;c-PrCH2,c-Pr,CF3],[RY1415;c-PrCH2,c-Pr,CF3CH2],[RY1416;c-PrCH2,c-Pr,CF3CF2],[RY1417;c-PrCH2,c-Pr,CF2H],[RY1418;c-PrCH2,c-Pr,CF2HCH2],[RY1419;i-Bu,c-Pr,c-Pr],[RY1420;i-Bu,c-Pr,t-Bu],[RY1421;i-Bu,c-Pr,Bu],[RY1422;i-Bu,c-Pr,t-Bu],[RY1423;i-Bu,c-Pr,c-PrCH2],[RY1424;i-Bu,c-Pr,Ph],[RY1425;i-Bu,c-Pr,Bn],[RY1426;i-Bu,c-Pr,CF3],[RY1427;i-Bu,c-Pr,CF3CH2],[RY1428;i-Bu,c-Pr,CF3CF2],[RY1429;i-Bu,c-Pr,CF2H],[RY1430;i-Bu,c-Pr,CF2HCH2],[RY1431;CF3CH2,c-Pr,c-Pr],[RY1432;CF3CH2,c-Pr,t-Bu],[RY1433;CF3CH2,c-Pr,Bu],[RY1434;CF3CH2,c-Pr,t-Bu],[RY1435;CF3CH2,c-Pr,c-PrCH2],[RY1436;CF3CH2,c-Pr,Ph],[RY1437;CF3CH2,c-Pr,Bn],[RY1438;CF3CH2,c-Pr,CF3],[RY1439;CF3CH2,c-Pr,CF3CH2],[RY1440;CF3CH2,c-Pr,CF3CF2],[RY1441;CF3CH2,c-Pr,CF2H],[RY1442;CF3CH2,c-Pr,CF2HCH2],[RY1443;CF2HCH2,c-Pr,c-Pr],[RY1444;CF2HCH2,c-Pr,t-Bu],[RY1445;CF2HCH2,c-Pr,Bu],[RY1446;CF2HCH2,c-Pr,t-Bu],[RY1447;CF2HCH2,c-Pr,c-PrCH2],[RY1448;CF2HCH2,c-Pr,Ph],[RY1449;CF2HCH2,c-Pr,Bn],[RY1450;CF2HCH2,c-Pr,CF3],[RY1451;CF2HCH2,c-Pr,CF3CH2],[RY1452;CF2HCH2,c-Pr,CF3CF2],[RY1453;CF2HCH2,c-Pr,CF2H],[RY1454;CF2HCH2,c-Pr,CF2HCH2],[RY1455;MeOCH2,c-Pr,c-Pr],[RY1456;MeOCH2,c-Pr,t-Bu],[RY1457;MeOCH2,c-Pr,Bu],[RY1458;MeOCH2,c-Pr,t-Bu],[RY1459;MeOCH2,c-Pr,c-PrCH2],[RY1460;MeOCH2,c-Pr,Ph],[RY1461;MeOCH2,c-Pr,Bn],[RY1462;MeOCH2,c-Pr,CF3],[RY1463;MeOCH2,c-Pr,CF3CH2],[RY1464;MeOCH2,c-Pr,CF3CF2],[RY1465;MeOCH2,c-Pr,CF2H],[RY1466;MeOCH2,c-Pr,CF2HCH2],[RY1467;EtOCH2,c-Pr,c-Pr],[RY1468;EtOCH2,c-Pr,t-Bu],[RY1469;EtOCH2,c-Pr,Bu],[RY1470;EtOCH2,c-Pr,t-Bu],[RY1471;EtOCH2,c-Pr,c-PrCH2],[RY1472;EtOCH2,c-Pr,Ph],[RY1473;EtOCH2,c-Pr,Bn],[RY1474;EtOCH2,c-Pr,CF3],[RY1475;EtOCH2,c-Pr,CF3CH2],[RY1476;EtOCH2,c-Pr,CF3CF2],[RY1477;EtOCH2,c-Pr,CF2H],[RY1478;EtOCH2,c-Pr,CF2HCH2],[RY1479;MeSCH2,c-Pr,c-Pr],[RY1480;MeSCH2,c-Pr,t-Bu],[RY1481;MeSCH2,c-Pr,Bu],[RY1482;MeSCH2,c-Pr,t-Bu],[RY1483;MeSCH2,c-Pr,c-PrCH2],[RY1484;MeSCH2,c-Pr,Ph],[RY1485;MeSCH2,c-Pr,Bn],[RY1486;MeSCH2,c-Pr,CF3],[RY1487;MeSCH2,c-Pr,CF3CH2],[RY1488;MeSCH2,c-Pr,CF3CF2],[RY1489;MeSCH2,c-Pr,CF2H],[RY1490;MeSCH2,c-Pr,CF2HCH2],[RY1491;EtSCH2,c-Pr,c-Pr],[RY1492;EtSCH2,c-Pr,t-Bu],[RY1493;EtSCH2,c-Pr,Bu],[RY1494;EtSCH2,c-Pr,t-Bu],[RY1495;EtSCH2,c-Pr,c-PrCH2],[RY1496;EtSCH2,c-Pr,Ph],[RY1497;EtSCH2,c-Pr,Bn],[RY1498;EtSCH2,c-Pr,CF3],[RY1499;EtSCH2,c-Pr,CF3CH2],[RY1500;EtSCH2,c-Pr,CF3CF2],[RY1501;EtSCH2,c-Pr,CF2H],[RY1502;EtSCH2,c-Pr,CF2HCH2],[RY1503;Ph,c-Pr,c-Pr],[RY1504;Ph,c-Pr,t-Bu],[RY1505;Ph,c-Pr,Bu],[RY1506;Ph,c-Pr,t-Bu],[RY1507;Ph,c-Pr,c-PrCH2],[RY1508;Ph,c-Pr,Ph],[RY1509;Ph,c-Pr,Bn],[RY1510;Ph,c-Pr,CF3],[RY1511;Ph,c-Pr,CF3CH2],[RY1512;Ph,c-Pr,CF3CF2],[RY1513;Ph,c-Pr,CF2H],[RY1514;Ph,c-Pr,CF2HCH2],[RY1515;Bn,c-Pr,c-Pr],[RY1516;Bn,c-Pr,t-Bu],[RY1517;Bn,c-Pr,Bu],[RY1518;Bn,c-Pr,t-Bu],[RY1519;Bn,c-Pr,c-PrCH2],[RY1520;Bn,c-Pr,Ph],[RY1521;Bn,c-Pr,Bn],[RY1522;Bn,c-Pr,CF3],[RY1523;Bn,c-Pr,CF3CH2],[RY1524;Bn,c-Pr,CF3CF2],[RY1525;Bn,c-Pr,CF2H],[RY1526;Bn,c-Pr,CF2HCH2],[RY1527;HCCCH2,c-Pr,c-Pr],[RY1528;HCCCH2,c-Pr,t-Bu],[RY1529;HCCCH2,c-Pr,Bu],[RY1530;HCCCH2,c-Pr,t-Bu],[RY1531;HCCCH2,c-Pr,c-PrCH2],[RY1532;HCCCH2,c-Pr,Ph],[RY1533;HCCCH2,c-Pr,Bn],[RY1534;HCCCH2,c-Pr,CF3],[RY1535;HCCCH2,c-Pr,CF3CH2],[RY1536;HCCCH2,c-Pr,CF3CF2],[RY1537;HCCCH2,c-Pr,CF2H],[RY1538;HCCCH2,c-Pr,CF2HCH2],[RY1539;CH3CCCH2,c-Pr,c-Pr],[RY1540;CH3CCCH2,c-Pr,t-Bu],[RY1541;CH3CCCH2,c-Pr,Bu],[RY1542;CH3CCCH2,c-Pr,t-Bu],[RY1543;CH3CCCH2,c-Pr,c-PrCH2],[RY1544;CH3CCCH2,c-Pr,Ph],[RY1545;CH3CCCH2,c-Pr,Bn],[RY1546;CH3CCCH2,c-Pr,CF3],[RY1547;CH3CCCH2,c-Pr,CF3CH2],[RY1548;CH3CCCH2,c-Pr,CF3CF2],[RY1549;CH3CCCH2,c-Pr,CF2H],[RY1550;CH3CCCH2,c-Pr,CF2HCH2] [RY 1401; c-Pr, c-Pr, Bn], [RY 1402; c-Pr, c-Pr, CF 3 ], [RY 1403; c-Pr, c-Pr, CF 3 CH 2 ], [RY 1404; c -Pr, c-Pr, CF 3 CF 2], [RY1405; c-Pr, c-Pr, CF 2 H], [RY1406; c-Pr, c-Pr, CF 2 HCH 2], [RY1407; c -PrCH 2, c-Pr, c -Pr], [RY1408; c-PrCH 2, c-Pr, t-Bu], [RY1409; c-PrCH 2, c-Pr, Bu], [RY1410; c- PrCH 2 , c-Pr, t-Bu], [RY 1411; c-PrCH 2 , c-Pr, c-PrCH 2 ], [RY 1412; c-PrCH 2 , c-Pr, Ph], [RY 1413; c- PrCH 2, c-Pr, Bn ], [RY1414; c-PrCH 2, c-Pr, CF 3], [RY1415; c-PrCH 2, c-Pr, CF 3 CH 2], [RY1416; c-PrCH 2, c-Pr, CF 3 CF 2], [RY1417; c-PrCH 2, c-Pr, CF 2 H], [RY1418; c-PrCH 2, c-Pr, CF 2 HCH 2], [RY1419; i-Bu, c-Pr, c-Pr], [RY 1420; i-Bu, c-Pr, t-Bu], [RY 1421; i-Bu, c-Pr, Bu], [RY 1422; i-Bu, c-Pr, t-Bu], [RY 1423; i-Bu, c-Pr, c-PrCH 2 ], [RY 1424; i-Bu, c-Pr, Ph], [RY 1425; i-Bu, c-Pr , Bn], [RY 1426; i-Bu, c-Pr, CF 3 ], [RY 1427; i-Bu, c-Pr, CF 3 CH 2 ], [RY 1428; i-Bu, c-Pr, CF 3 CF 2 ], [RY 1429; i-Bu, c-Pr, CF 2 H], [RY 1430; i-Bu, c-Pr, CF 2 HCH 2 ], [RY 1431; CF 3 CH 2 , c-Pr, c- Pr], [RY1432; CF 3 CH 2, c-Pr, t-Bu], [RY1433; CF 3 CH 2, c-Pr, Bu], [RY1434; CF 3 CH 2, c-Pr, t-Bu ], [RY 1435; CF 3 CH 2 , c-Pr, c-PrCH 2 ], [RY 14 36; CF 3 CH 2, c -Pr, Ph], [RY1437; CF 3 CH 2, c-Pr, Bn], [RY1438; CF 3 CH 2, c-Pr, CF 3], [RY1439; CF 3 CH 2, c-Pr, CF 3 CH 2], [RY1440; CF 3 CH 2, c-Pr, CF 3 CF 2], [RY1441; CF 3 CH 2, c-Pr, CF 2 H], [RY1442 CF 3 CH 2 , c-Pr, CF 2 HCH 2 ], [RY 1443; CF 2 HCH 2 , c-Pr, c-Pr], [RY 1444; CF 2 HCH 2 , c-Pr, t-Bu], [RY1445; CF 2 HCH 2, c-Pr, Bu], [RY1446; CF 2 HCH 2, c-Pr, t-Bu], [RY1447; CF 2 HCH 2, c-Pr, c-PrCH 2], [RY1448; CF 2 HCH 2, c-Pr, Ph], [RY1449; CF 2 HCH 2, c-Pr, Bn], [RY1450; CF 2 HCH 2, c-Pr, CF 3], [RY1451; CF 2 HCH 2, c-Pr, CF 3 CH 2], [RY1452; CF 2 HCH 2, c-Pr, CF 3 CF 2], [RY1453; CF 2 HCH 2, c-Pr, CF 2 H], [ RY1454; CF 2 HCH 2, c -Pr, CF 2 HCH 2], [RY1455; MeOCH 2, c-Pr, c-Pr], [RY1456; MeOCH 2, c-Pr, t-Bu], [RY1457; MeOCH 2, c-Pr, Bu ], [RY1458; MeOCH 2, c-Pr, t-Bu], [RY1459; MeOCH 2, c-Pr, c-PrCH 2], [RY1460; MeOCH 2, c-Pr , Ph], [RY1461; MeOCH 2, c-Pr, Bn], [RY1462; MeOCH 2, c-Pr, CF 3], [RY1463; MeOCH 2, c-Pr, CF 3 CH 2], [RY1464; MeOCH 2 , c-Pr, CF 3 CF 2 ], [RY1465; MeOCH 2 , c-Pr, CF 2 H], [RY 1466; MeOCH 2 , c-Pr, CF 2 HCH 2 ], [RY 1467; EtOCH 2 , c-Pr, c-Pr] , [RY 1468; EtOCH 2 , c-Pr, t-Bu], [RY 1469; EtOCH 2 , c-Pr, Bu], [RY 1470; EtOCH 2 , c-Pr, t-Bu], [RY 1471; EtOCH 2 , c-Pr, c-PrCH 2 ], [RY1472; EtOCH 2 , c-Pr, Ph], [RY 1473; EtOCH 2 , c-Pr, Bn], [RY 1474; EtOCH 2 , c-Pr, CF 3 ], [RY1475; EtOCH 2, c- Pr, CF 3 CH 2], [RY1476; EtOCH 2, c-Pr, CF 3 CF 2], [RY1477; EtOCH 2, c-Pr, CF 2 H], [RY1478; EtOCH 2 , c-Pr, CF 2 HCH 2 ], [RY 1479; MeSCH 2 , c-Pr, c-Pr], [RY 1480; MeSCH 2 , c-Pr, t-Bu], [RY 1481; MeSCH 2 , c -Pr, Bu], [RY1482; MeSCH 2, c-Pr, t-Bu], [RY1483; MeSCH 2, c-Pr, c-PrCH 2], [RY1484; MeSCH 2, c-Pr, Ph], [RY1485; MeSCH 2, c- Pr, Bn], [RY1486; MeSCH 2, c-Pr, CF 3], [RY1487; MeSCH 2, c-Pr, CF 3 CH 2], [RY1488; MeSCH 2, c -Pr, CF 3 CF 2], [RY1489; MeSCH 2, c-Pr, CF 2 H], [RY1490; MeSCH 2, c-Pr, CF 2 HCH 2], [RY1491; EtSCH 2, c-Pr, c-Pr], [RY1492; EtSCH 2, c-Pr, t-Bu], [RY1493; EtSCH 2, c-Pr, Bu], [RY1494; EtSCH 2, c-Pr, t-Bu], [RY1495 EtSCH 2 , c-Pr, c-PrCH 2 ], [RY 1496; EtSCH 2 , c-Pr, Ph], [RY 1497; EtSCH 2 , c-Pr, Bn], [RY 1498; EtSCH 2 , c-Pr, CF 3 ], [RY 1499; EtSCH 2 , c-Pr, CF 3 CH 2 ], [RY 1500; EtSCH 2 , c-Pr, CF 3 CF 2 ], [RY 1501; EtSCH 2 , c-Pr , CF 2 H], [RY 1502; EtSCH 2 , c-Pr, CF 2 HCH 2 ], [RY 1503; Ph, c-Pr, c-Pr], [RY 1504; Ph, c-Pr, t-Bu], [RY1505; Ph, c-Pr , Bu], [RY1506; Ph, c-Pr, t-Bu], [RY1507; Ph, c-Pr, c-PrCH 2], [RY1508; Ph, c-Pr, Ph], [RY 1509; Ph, c-Pr, Bn], [RY 1510; Ph, c-Pr, CF 3 ], [RY 1511; Ph, c-Pr, CF 3 CH 2 ], [RY 1512; Ph, c- Pr, CF 3 CF 2], [RY1513; Ph, c-Pr, CF 2 H], [RY1514; Ph, c-Pr, CF 2 HCH 2], [RY1515; Bn, c-Pr, c-Pr] , [RY 1516; Bn, c-Pr, t-Bu], [RY 1517; Bn, c-Pr, Bu], [RY 1518; Bn, c-Pr, t-Bu], [RY 1519; Bn, c-Pr, c-PrCH 2], [RY1520 ; Bn, c-Pr, Ph], [RY1521; Bn, c-Pr, Bn], [RY1522; Bn, c-Pr, CF 3], [RY1523; Bn, c- Pr, CF 3 CH 2], [RY1524; Bn, c-Pr, CF 3 CF 2], [RY1525; Bn, c-Pr, CF 2 H], [RY1526; Bn, c-Pr, CF 2 HCH 2 ], [RY1527; HCCCH 2, c-Pr, c-Pr], [RY1528; HCCCH 2, c-Pr, t-Bu], [RY1529; HCCCH 2, c-Pr, Bu], [RY1530; HCCCH 2 , c-Pr, t-Bu ], [RY1531; HCCCH 2, c-Pr, c-PrCH 2], [RY1532; HCCCH 2, c-Pr, Ph], [RY1533; HCCCH 2, c-Pr, Bn ], [RY1534; HCCCH 2, c-Pr, CF 3], [RY1535; HCCCH 2, c-Pr, CF 3 CH 2], [RY1536; HCCCH 2, c-Pr, CF 3 CF 2], [RY1537 ; HCCCH 2, c-Pr, CF 2 H], [RY1538; HCCCH 2, c-Pr, CF 2 HCH 2], [RY1539; CH 3 CCCH 2, c-Pr, c-P r], [RY1540; CH 3 CCCH 2, c-Pr, t-Bu], [RY1541; CH 3 CCCH 2, c-Pr, Bu], [RY1542; CH 3 CCCH 2, c-Pr, t-Bu ], [RY1543; CH 3 CCCH 2, c-Pr, c-PrCH 2], [RY1544; CH 3 CCCH 2, c-Pr, Ph], [RY1545; CH 3 CCCH 2, c-Pr, Bn], [RY1546; CH 3 CCCH 2, c-Pr, CF 3], [RY1547; CH 3 CCCH 2, c-Pr, CF 3 CH 2], [RY1548; CH 3 CCCH 2, c-Pr, CF 3 CF 2 ], [RY1549; CH 3 CCCH 2, c-Pr, CF 2 H], [RY1550; CH 3 CCCH 2, c-Pr, CF 2 HCH 2]

本発明化合物RA、本発明化合物RB、本発明化合物RC、本発明化合物RD、本発明化合物RE、本発明化合物RF、本発明化合物RG、本発明化合物RH、本発明化合物RI、本発明化合物RJ、本発明化合物RK、本発明化合物RL、本発明化合物RM、本発明化合物RN、本発明化合物RO、本発明化合物RP、本発明化合物RQ、本発明化合物RR、本発明化合物RS、本発明化合物RT、本発明化合物RU、本発明化合物RV、本発明化合物RW、本発明化合物RX及び本発明化合物RYを本発明化合物Aと記す。   The compound RA of the present invention, the compound RB of the present invention, the compound RC of the present invention, the compound RE of the present invention, the compound RF of the present invention, the compound RG of the present invention, the compound RH of the present invention, the compound RI of the present invention The compound RK of the present invention, the compound RL of the present invention, the compound RM of the present invention, the compound RO of the present invention, the compound RP of the present invention, the compound RQ of the present invention, the compound RR of the present invention, the compound RS of the present invention, the compound RT of the present invention The compound RU of the invention, the compound RV of the invention, the compound RW of the invention, the compound RX of the invention and the compound RY of the invention are referred to as a compound A of the invention.

本発明化合物は、殺菌剤、殺虫剤、殺ダニ剤、殺センチュウ剤、植物成長調節剤又は共力剤(以下、まとめて本成分と記す。)と、混用又は併用することができる。そして、殺菌剤、殺虫剤、殺ダニ剤、殺センチュウ剤、植物成長調節剤及び共力剤からなる群より選ばれる1以上、並びに、本発明化合物を含有する組成物を植物又は土壌に処理することにより、有害節足動物、有害線形動物、及び植物病原菌等の有害生物を防除することができる。また、本発明化合物と本成分とを別々に施用して、有害生物を防除することができる。
殺菌剤とは、植物病原菌(糸状菌や細菌)に由来する病害から植物を守るために使用する成分であり、例えばFRAC(Fungicide Resistance Action Committee:殺菌剤耐性菌対策委員会)等で規定されるものが挙げられる。
殺虫剤、殺ダニ剤及び殺センチュウ剤としては、例えばIRAC(Insecticide Resistance Action Committee:殺虫剤抵抗性対策委員会)等で規定されるものが挙げられる。
植物成長調節剤とは、着果促進、発根促進のように、植物の成長を調整する成分を意味し、例えばインドール酪酸が挙げられる。
共力剤とは、他の剤と混合又は併用して用いた場合に、その剤の効力を増強する成分を意味し、例えばピペロニルブトキシドが挙げられる。
The compound of the present invention can be used in combination or in combination with a bactericidal agent, an insecticide, an acaricide, a nematode, a plant growth regulator or a synergist (hereinafter collectively referred to as the present component). Then, a plant or soil is treated with a composition containing one or more members selected from the group consisting of fungicides, insecticides, acaricides, nematocides, plant growth regulators and synergists, and the compound of the present invention. Thus, pests such as harmful arthropods, harmful linear animals, and plant pathogens can be controlled. Furthermore, pests can be controlled by separately applying the compound of the present invention and the component.
A bactericidal agent is a component used to protect plants from diseases caused by plant pathogens (filamentous fungi and bacteria), and is defined, for example, by the FRAC (Fungicide Resistance Action Committee) The thing is mentioned.
Examples of the insecticide, acaricide and nematocide include those specified by IRAC (Insecticide Resistance Action Committee: Insecticide Resistance Measures Committee) and the like.
The plant growth regulator means a component that regulates plant growth, such as promoting fruit set and rooting, and examples include indole butyric acid.
By a synergist is meant a component that enhances the efficacy of the agent when used in admixture with or in combination with other agents, such as piperonyl butoxide.

以下に、本発明化合物と本成分との組合せの例を記載する。例えば、テブコナゾール(tebuconazole)+SXは、テブコナゾール(tebuconazole)とSXとの組合せを意味する。尚、SXの略号は本発明化合物Aから選ばれるいずれか1つの化合物を意味する。また、括弧内の数字はCAS登録番号を表す。
テブコナゾール(tebuconazole)+SX、プロチオコナゾール(prothioconazole)+SX、メトコナゾール(metconazole)+SX、イプコナゾール(ipconazole)+SX、トリチコナゾール(triticonazole)+SX、ジフェノコナゾール(difenoconazole)+SX、イマザリル(imazalil)+SX、トリアジメノール(triadimenol)+SX、テトラコナゾール(tetraconazole)+SX、フルトリアホール(flutriafol)+SX、ブロムコナゾール(bromuconazole)+SX、プロピコナゾール(propiconazole)+SX、メフェントリフルコナゾール(mefentrifluconazole)+SX、イプフェントリフルコナゾール(ipfentrifluconazole)+SX、エポキシコナゾール(epoxiconazole)+SX、シプロコナゾール(cyproconazole)+SX、マンデストロビン(mandestrobin)+SX、アゾキシストロビン(azoxystrobin)+SX、ピラクロストロビン(pyraclostrobin)+SX、トリフロキシストロビン(trifloxystrobin)+SX、フルオキサストロビン(fluoxastrobin)+SX、ピコキシストロビン(picoxystrobin)+SX、フェナミドン(fenamidone)+SX、ジモキシストロビン(dimoxystrobin)+SX、メトミノストロビン(metominostrobin)+SX、ピリベンカルブ(pyribencarb)+SX、セダキサン(sedaxane)+SX、ペンフルフェン(penflufen)+SX、フルキサピロキサド(fluxapyroxad)+SX、フルオピラム(fluopyram)+SX、ベンゾビンジフルピル(benzovindiflupyr)+SX、ボスカリド(boscalid)+SX、カルボキシン(carboxin)+SX、ペンチオピラド(penthiopyrad)+SX、フルトラニル(flutolanil)+SX、ビキサフェン(bixafen)+SX、ピジフルメトフェン(pydiflumetofen)+SX、3−ジフルオロメチル−N−(7−フルオロ−1,1,3−トリメチルインダン−4−イル)−1−メチルピラゾール−4−カルボキサミド(1383809-87-7)+SX、N−シクロプロピル−3−(ジフルオロメチル)−5−フルオロ−N−(5−クロロ−2−イソプロピルベンジル)−1−メチル−1H−ピラゾール−4−カルボキサミド(1255734-28-1)+SX、3−ジフルオロメチル−1−メチル−N−(1,1,3−トリメチルインダン−4−イル)ピラゾール−4−カルボキサミド(141573-94-6)+SX、3−ジフルオロメチル−1−メチル−N−[(3R)−1,1,3−トリメチルインダン−4−イル]ピラゾール−4−カルボキサミド(1352994-67-2)+SX、メタラキシル(metalaxyl)+SX、メタラキシルM(metalaxyl-M)+SX、メトラフェノン(metrafenone)+SX、シフルフェナミド(cyflufenamid)+SX、プロキナジド(proquinazid)+SX、3−クロロ−5−フェニル−6−メチル−4−(2,6−ジフルオロフェニル)ピリダジン(1358061-55-8)+SX、1−(2−{[1−(4−クロロフェニル)−1H−ピラゾール−3−イル]オキシメチル}−3−メチルフェニル)−4−メチル−1,4−ジヒドロテトラゾール−5−オン(1472649-01-6)+SX、4−(2−ブロモ−4−フルオロフェニル)−N−(2−クロロ−6−フルオロフェニル)−1,3−ジメチル−1H−ピラゾール−5−アミン(1362477-26-6)+SX、(3S,6S,7R,8R)−8−ベンジル−3−[({3−[(イソブチリルオキシ)メトキシ]−4−メトキシピリジン−2−イル}カルボニル)アミノ]−6−メチル−4,9−ジオキソ−1,5−ジオキソナン−7−イル−2−メチルプロパネート(517875-34-2)+SX、N’−(2,5−ジメチル−4−フェノキシフェニル)−N−エチル−N−メチルメタンイミドアミド(1052688-31-9)+SX、イソチアニル(isotianil)+SX、オキソリニック酸(oxolinic acid)+SX、フェリムゾン(ferimzone)+SX、フサライド(phthalide)+SX、カスガマイシン(kasugamycin)+SX、テブフロキン(tebufloquin)+SX、キノフメリン(quinofumelin)+SX、フェンピラザミン(fenpyrazamine)+SX、プロシミドン(procymidone)+SX、フルジオキソニル(fludioxonil)+SX、トルクロホスメチル(tolclofos-methyl)+SX、チアベンダゾール(thiabendazole)+SX、エタボキサム(ethaboxam)+SX、ピカルブトラゾクス(picarbutrazox)+SX、オキサチアピプロリン(oxathiapiprolin)+SX、イミノクタジン酢酸塩(iminoctadine triacetate)+SX、イミノクタジンアルベシル酸塩(iminoctadine albesilate)+SX、フェンプロピモルフ(fenpropimorph)+SX、フェンプロピジン(fenpropidin)+SX、スピロキサミン(spiroxamine)+SX、クロロタロニル(chlorothalonil)+SX、フォルペット(folpet)+SX、キャプタン(captan)+SX、チウラム(thiram)+SX、シルチオファム(silthiofam)+SX、マンコゼブ(mancozeb)+SX、カルタップ(cartap)+SX、クロチアニジン(clothianidin)+SX、チアメトキサム(thiamethoxam)+SX、イミダクロプリド(imidacloprid)+SX、チアクロプリド(thiacloprid)+SX、フルピラジフロン(flupyradifurone)+SX、スルホキサフロル(sulfoxaflor)+SX、トリフルメゾピリム(triflumezopyrim)+SX、ジクロロメゾチアズ(dicloromezotiaz)+SX、ベータシフルトリン(beta-cyfluthrin)+SX、テフルトリン(tefluthrin)+SX、フィプロニル(fipronil)+SX、クロラントラニリプロール(chlorantraniliprole)+SX、シアントラニリプロール(cyantraniliprole)+SX、テトラニリプロール(tetraniliprole)+SX、チオジカルブ(thiodicarb)+SX、カルボフラン(carbofuran)+SX、フルキサメタミド(fluxametamide)+SX、アフォキソラネル(afoxolaner)+SX、フルララネル(fluralaner)+SX、ブロフラニリド(broflanilide)+SX、アバメクチン(abamectin)+SX、フルエンスルホン(fluensulfone)+SX、フルアザインドリジン(fluazaindolizine)+SX、チオキサザフェン(tioxazafen)+SX、(E)−N−{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(1689566-03-7)+SX、菌根菌(Mycorrhizal Fungi)+SX、バチルス・フィルムス菌(Bacillus firmus)+SX、バチルス・アミロリケファシエンス菌(Bacillus amyloliquefaciens)+SX、パスツーリア・ニシザワエ菌(Pasteuria nishizawae)+SX、パスツーリア・ペネトランス菌(Pasteuria penetrans)+SX。
Below, the example of the combination of this invention compound and this component is described. For example, tebuconazole (tebuconazole) + SX means a combination of tebuconazole (tebuconazole) and SX. The abbreviation SX means any one compound selected from the compound A of the present invention. Also, numbers in parentheses indicate CAS registration numbers.
Tebuconazole (tebuconazole) + SX, prothioconazole (prothioconazole) + SX, metconazole (metconazole) + SX, ipconazole (ipconazole) + SX, triticonazole (triticonazole) + SX, difenoconazole (difenoconazole) + SX, imazalil (imazailil) + triadimenol + SX, tetraconazole (tetraconazole) + SX, flutriafol + SX, bromuconazole (bromuconazole) + SX, propiconazole + SX, mefentrifluconazole (mefentrifluconazole) + SX, Ipfentrifluconazole ( ipfentrifluconazole) + SX, epoxiconazole (Epoxiconazole) + SX, cyproconazole (cyproconazole) + SX, mandestorobin (mandestrobin) + SX, azoxystrobin (Saxoxystrobin) + SX, pyraclostrobin (pyraclostrobin) + SX, trifloxystrobin (Pyraclostrobin) trifloxystrobin) + SX, fluoxast Robin (fluoxastrobin) + SX, picoxystrobin (SX), fenamidone + SX, dimoxystrobin (DX) + SX, metominostrobin + SX, pyribencarb (Pyribencarb) + SX, sedaxane + SX, Penflufen + SX, fluxapyroxad + SX, fluopyram (+ flupyram) + SX, benzovindiflupyr + SX, boscalid + SX, carboxin + SX, penthiopyrad + SX, flutranyl (flutolanil) + SX, bixafen + SX, pydiflumetofen + SX, 3-difluoromethyl-N- (7-fluoro-1,1,3-trimethylindan-4-yl) -1-methylpyrazole -4-carboxamide (1383809-87-7) + SX, N-cyclopropyl-3- (difluoromethyl) -5 Fluoro-N- (5-chloro-2-isopropylbenzyl) -1-methyl-1H-pyrazole-4-carboxamide (1255734-28-1) + SX, 3-difluoromethyl-1-methyl-N- (1,1 3, 3-trimethylindan-4-yl) pyrazole-4-carboxamide (141573-94-6) + SX, 3-difluoromethyl-1-methyl-N-[(3R) -1,1,3-trimethylindan-4 -Yl] pyrazole-4-carboxamide (1352994-67-2) + SX, metalaxyl (metalaxyl) + SX, metalaxyl M (metalaxyl-M) + SX, metrafenone (Straight) + Siflufenamide (cyflufenamid) + SX, proquinazid + SX, 3-chloro-5-phenyl-6-methyl-4- (2,6-difluorophenyl) pyridazine (1358061-55-8) + SX, 1- (2-{[1- (4-chlorophenyl) -1H-pi] [Sol-3-yl] oxymethyl} -3-methylphenyl) -4-methyl-1,4-dihydrotetrazol-5-one (1472649-01-6) + SX, 4- (2-bromo-4-fluorophenyl) ) -N- (2-Chloro-6-fluorophenyl) -1,3-dimethyl-1H-pyrazol-5-amine (1362477-26-6) + SX, (3S, 6S, 7R, 8R) -8-benzyl -3-[({3-[(isobutyryloxy) methoxy] -4-methoxypyridin-2-yl} carbonyl) amino] -6-methyl-4,9-dioxo-1,5-dioxonan-7 Yl-2-methylpropanate (517875-34-2) + SX, N '-(2,5-dimethyl-4-phenoxyphenyl) -N-ethyl-N-methylmethanimidamide (1052688- 31-9) + SX , Isotianil (isotianil) + SX, oxolinic acid SX, ferrimzone + SX, phthalide + SX, kasugamycin (kasugamicin) + SX, tebufloquine + SX, quinofumelin + SX, fenpyrazamine + SX, procymidone (Sucymonone) + SX, fludioxil + Tolclofos-methyl (stoclofos-methyl) + SX, thiabendazole (thiabendazole) + SX, etaboxam (ethaboxam) + SX, picalbutrazox (picarbutrazox) + SX, oxathiapiprolin + SX, imintagazine acetate (iminoctadine triacetate) + SX Silicate (iminooctadine albesilate) + SX, fenpropimorph + SX, fenpropidin + SX, spiroxamine + SX, chlorothalonil + SX, folpet + SX, captan + SX, Thiuram (thiram) + SX, sill off (Silthiofam) + SX, mancozeb (mancozeb) + SX, cartap (cartap) + SX, clothianidin + SX, thiamethoxam + SX, imidacloprid + SX, thiacloprid (thiaclop) + SX, flupyrisulfurone (Sulfoxaflor) + SX, Triflumezopyrim + SX, Dichloromezotiaz (Dicloromezotiaz) + SX, Beta-cyfluthrin (beta-cyfluthrin) + SX, Tefluthrin (tefluthrin) + SX, Fipronil (fipronil) + SX, Chlorantraniliprol (chlorantranprole ) + SX, cyantraniliprole + SX, tetraniliprol (tetraniliprole) + SX, thiodicarb + thiocarb + SX, carbofuran + SX, fluxametamide + SX, afoxolaner + SX, fluralaner + Broflanilid e) + SX, abamectin + SX, fluensulfone + SX, fluazaindolizine + SX, tiozafafen + SX, (E) -N- {1-[(6-chloropyridine-3-) [Ill) methyl] pyridin-2 (1H) -ylidene} -2, 2, 2-trifluoroacetamide (1689566-03-7) + SX, Mycorrhizal Fungi + SX, Bacillus firmus (Bacillus firmus) + SX, Bacillus amyloliquefaciens + SX, Pasteuria nishizawae + SX, Pasteuria penetrans + SX.

本発明化合物と本成分との比は、特に限定されるものではないが、重量比(本発明化合物:本成分)で1000:1〜1:1000、500:1〜1:500、100:1〜1:100、50:1〜1:50、20:1〜1:20、10:1〜1:10、3:1〜1:3、1:1〜1:500、1:1〜1:100、1:1〜1:50、1:1〜1:20、1:1〜1:10等が挙げられる。 The ratio of the compound of the present invention to the component is not particularly limited, but the weight ratio (the compound of the present invention: component) is from 1000: 1 to 1: 1000, 500: 1 to 1: 500, 100: 1. To 1: 100, 50: 1 to 1:50, 20: 1 to 1:20, 10: 1 to 1:10, 3: 1 to 1: 3, 1: 1 to 1: 500, 1: 1 to 1 : 100, 1: 1 to 1:50, 1: 1 to 1:20, 1: 1 to 1:10 and the like.

本発明化合物を植物に処理することにより、苗立ち率向上、健全葉数増加、草丈増、植物体重量増加、葉面積増加、種子又は果実の数又は重量の増加、着花数又は着果数の増加、根部生長の増加等の、植物の成長を促進する効果が得られる。また、本発明化合物を植物に処理することにより、高温ストレスもしくは低温ストレス等の温度ストレス、乾燥ストレスもしくは過湿ストレス等の水分ストレス、又は塩ストレス等の非生物的ストレスに対する耐性が向上される。   By treating the compound of the present invention on plants, the seedling establishment rate, healthy leaf number increase, plant height increase, plant body weight increase, leaf area increase, number or weight of seeds or fruits, number of set flowers or number of fruits set The effect of promoting plant growth such as increase of root growth and increase of root growth can be obtained. Furthermore, by treating the compound of the present invention on plants, tolerance to temperature stress such as high temperature stress or low temperature stress, water stress such as drought stress or excessive humidity stress, or abiotic stress such as salt stress is improved.

次に製剤例を示す。なお、製剤例において部とは重量部を表す。   Next, formulation examples are shown. In the preparation examples, "part" means "part by weight".

製剤例1 本発明化合物Aのいずれか1化合物50部、リグニンスルホン酸カルシウム3部、ラウリル硫酸マグネシウム2部及び合成含水酸化珪素45部をよく粉砕混合することにより、製剤を得る。 Formulation Example 1 A formulation is obtained by thoroughly grinding and mixing 50 parts of any one compound of the present invention A, 3 parts of calcium lignin sulfonate, 2 parts of magnesium lauryl sulfate and 45 parts of synthetic hydrous silicon oxide.

製剤例2 本発明化合物Aのいずれか1化合物20部とソルビタントリオレエート1.5部とを、ポリビニルアルコール2部を含む水溶液28.5部と混合し、湿式粉砕法で微粉砕した後、この中に、キサンタンガム0.05部及びアルミニウムマグネシウムシリケート0.1部を含む水溶液40部を加え、さらにプロピレングリコール10部を加えて攪拌混合し、製剤を得る。 Formulation Example 2 20 parts of any one compound of the present invention A and 1.5 parts of sorbitan trioleate are mixed with 28.5 parts of an aqueous solution containing 2 parts of polyvinyl alcohol and finely ground by a wet grinding method, Into this, 40 parts of an aqueous solution containing 0.05 part of xanthan gum and 0.1 part of aluminum magnesium silicate is added, and 10 parts of propylene glycol is further added thereto, followed by stirring and mixing to obtain a preparation.

製剤例3 本発明化合物Aのいずれか1化合物2部、カオリンクレー88部及びタルク10部をよく粉砕混合することにより、製剤を得る。 Formulation Example 3 A formulation is obtained by thoroughly grinding and mixing 2 parts of any one compound of the present invention A, 88 parts of kaolin clay and 10 parts of talc.

製剤例4 本発明化合物Aのいずれか1化合物5部、ポリオキシエチレンスチリルフェニルエーテル14部、ドデシルベンゼンスルホン酸カルシウム6部及びキシレン75部をよく混合することにより、製剤を得る。 Formulation Example 4 A formulation is obtained by thoroughly mixing 5 parts of any one compound of the present invention A, 14 parts of polyoxyethylene styryl phenyl ether, 6 parts of calcium dodecylbenzene sulfonate and 75 parts of xylene.

製剤例5 本発明化合物Aのいずれか1化合物2部、合成含水酸化珪素1部、リグニンスルホン酸カルシウム2部、ベントナイト30部及びカオリンクレー65部をよく粉砕混合した後、水を加えてよく練り合せ、造粒乾燥することにより、製剤を得る。 Formulation Example 5 2 parts of any one compound of the present invention A, 1 part of synthetic hydrous silicon oxide, 2 parts of calcium lignin sulfonate, 30 parts of bentonite and 65 parts of kaolin clay are well ground and mixed, then water is added and kneaded well The formulation is obtained by combining, granulating and drying.

製剤例6 本発明化合物Aのいずれか1化合物20部;ホワイトカーボンとポリオキシエチレンアルキルエーテルサルフェートアンモニウム塩との混合物(重量割合1:1)35部及び水を混合し全量を100部とし、粉砕機を用いて処理することにより、製剤を得る。 Formulation Example 6 20 parts of any one compound of the present invention A; 35 parts of a mixture of white carbon and polyoxyethylene alkyl ether sulfate ammonium salt (weight ratio 1: 1) and water are mixed to make the total amount 100 parts, and ground The formulation is obtained by processing using a machine.

次に、本発明化合物が有害生物の防除に有用であることを試験例で示す。 The following Test Examples show that the compounds of the present invention are useful for controlling pests.

試験例1 コムギ葉枯病菌(Septoria tritici)に対する防除試験
本発明化合物3、4、5、11、13、14、21、45、64、79〜82、83又は85を1500ppm含有するようにジメチルスルホキシドで希釈し、タイタープレート(96ウェル)に1μL分注した後、あらかじめコムギ葉枯病菌の胞子を接種したジャガイモ煎汁液体培地(PDB培地)を150μL分注した。このプレートを5日間、18℃で培養しコムギ葉枯病菌を増殖させたのち、タイタープレートの各ウェルの550nmの吸光度を測定し、その値をコムギ葉枯病菌の生育度とした。その結果、本発明化合物3、4、5、11、13、14、21、45、64、79〜82、83又は85を処理した区における生育度はいずれも、無処理区における生育度の50%以下であった。
Test Example 1 Control test against wheat leaf blight fungus (Septoria tritici) Dimethylsulfoxide so as to contain 1500 ppm of the present compound 3, 4, 5, 11, 13, 14, 21, 21, 45, 64, 79-82, 83 or 85 And diluted with 1 μL into a titer plate (96 wells), and then 150 μL of potato juice liquid medium (PDB medium) inoculated with spores of wheat leaf blight fungus in advance was dispensed. The plate was cultured at 18 ° C. for 5 days to grow wheat leaf blight, and then the absorbance at 550 nm of each well of the titer plate was measured, and the value was defined as the viability of wheat leaf blight. As a result, in the groups treated with the compounds of the present invention 3, 4, 5, 11, 13, 14, 21, 45, 64, 79-82, 83 or 85, the growth rate in any of the groups was 50 % Or less.

試験例2 トマト葉かび病菌(Cladosporium fulvum)に対する防除試験
本発明化合物1、7、13、23、25、28、31、32、34、36、39〜45、47、54、59、61、71、74、77、79、80〜82、86〜88又は89を1500ppm含有するようにジメチルスルホキシドで希釈し、タイタープレート(96ウェル)に1μL分注した後、あらかじめトマト葉かび病菌(チトクロームbをコードする遺伝子のうち、チトクロームbの129番目のアミノ酸残基がフェニルアラニンからロイシンに置換されるよう塩基配列が変異したQoI耐性株)の胞子を接種したジャガイモ煎汁液体培地(PDB培地)を150μL分注した。このプレートを5日間、18℃で培養しトマト葉かび病菌を増殖させたのち、タイタープレートの各ウェルの550nmの吸光度を測定し、その値をトマト葉かび病菌の生育度とした。その結果、本発明化合物1、7、13、23、25、28、31、32、34、36、39〜45、47、54、59、61、71、74、77、79、80〜82、86〜88又は89を処理した区における生育度は、無処理区における生育度の50%以下であった。
Test Example 2 Control Test against Tomato Leaf Mold Fungus (Cladosporium fulvum) Compounds of the Present Invention 1, 7, 13, 23, 25, 28, 31, 32, 34, 36, 39-45, 47, 54, 59, 61, 71 , Diluted with dimethyl sulfoxide so that it contains 1500 ppm of 74, 77, 79, 80-82, 86-88 or 89, and dispensed 1 μL to a titer plate (96 wells), Among the genes encoded, 150 μL of potato juice liquid medium (PDB medium) inoculated with spores of QoI resistant strain in which the nucleotide sequence is mutated so that the 129th amino acid residue of cytochrome b is substituted from phenylalanine to leucine I ordered. This plate was cultured at 18 ° C. for 5 days to grow tomato leaf mold fungus, and then the absorbance at 550 nm of each well of the titer plate was measured, and the value was taken as the viability of tomato leaf mold fungus. As a result, the compounds 1, 7, 13, 23, 25, 28, 31, 32, 34, 36, 39 to 45, 47, 54, 59, 61, 71, 74, 77, 79, 80 to 82, The degree of growth in the section treated with 86 to 88 or 89 was 50% or less of the degree of growth in the untreated section.

試験例3 ダイズさび病(Phakopsora pachyrhizi)に対する防除試験
プラスチックポットに土壌を詰め、そこにダイズ(品種;黒千石)を播種し、温室内で10日間栽培し、ダイズさび病菌の夏胞子を含む水懸濁液を噴霧接種した。接種後ダイズを昼間23℃、夜間20℃の温室内で多湿下に1日間置き、次に温室で2日間栽培した後、製剤例6に記載の方法に準じて製剤化された本発明化合物1〜16、18〜37、39、40〜48、50〜58、60〜77、79〜86、88〜91又は92を濃度が200ppmとなるように水と混合し、該混合物を、上記ダイズの葉面に充分付着するように茎葉散布した。散布後ダイズを風乾し、温室内で8日間栽培した後、病斑面積を調査した。その結果、本発明化合物1〜16、18〜37、39、40〜48、50〜58、60〜77、79〜86、88〜91又は92を処理したダイズにおける病斑面積はいずれも、無処理のダイズにおける病斑面積の30%以下であった。
Test Example 3 Control Test for Soybean Rust (Phakopsora pachyrhizi) The soil is packed in a plastic pot, soya beans (variety: Kurosengoku) are sown, and grown in a greenhouse for 10 days, water containing Natsuspore of soybean rust fungus The suspension was spray inoculated. Present invention compound 1 formulated according to the method described in Formulation Example 6 after placing soybean under humid conditions in a greenhouse at daytime 23 ° C. and nighttime 20 ° C. after cultivation and then cultivating for 2 days in a greenhouse 16, 16, 18 to 37, 39, 40 to 48, 50 to 58, 60 to 77, 79 to 86, 88 to 91 or 92 are mixed with water to a concentration of 200 ppm, and the mixture is The foliage was sprayed so as to adhere well to the leaf surface. After spraying, the soybeans were air dried and cultivated for 8 days in a greenhouse, and then the lesion area was examined. As a result, as for the lesion area in the soybean which processed this invention compound 1-16, 18-37, 39, 40-48, 50-58, 60-77, 79-86, 88-91, or 92, all are none. It was less than 30% of the lesion area in treated soybean.

試験例4 ダイズさび病(Phakopsora pachyrhizi)に対する防除試験
プラスチックポットに土壌を詰め、そこにダイズ(品種;黒千石)を播種し、温室内で13日間栽培した。製剤例6に記載の方法に準じて製剤化された本発明化合物1、3〜16、18〜33、35〜48、50〜77、79、80、82〜86、88〜91又は92を濃度が200ppmとなるように水と混合し、該混合物を、上記ダイズの葉面に充分付着するように茎葉散布した。散布後ダイズを風乾し、4日後にダイズさび病菌の胞子を含む水懸濁液を噴霧接種した。接種後ダイズを昼間23℃、夜間20℃の温室内で多湿下に1日間置き、次に温室内で10日間栽培した後、病斑面積を調査した。その結果、本発明化合物1、3〜16、18〜33、35〜48、50〜77、79、80、82〜86、88〜91又は92を処理したダイズにおける病斑面積はいずれも、無処理のダイズにおける病斑面積の30%以下であった。
Test Example 4 Control Test for Soybean Rust (Phakopsora pachyrhizi) The soil was packed in a plastic pot, soya bean (variety: Kurosengoku) was sown and cultivated in a greenhouse for 13 days. Concentrations of the present compound 1, 3 to 16, 18 to 33, 35 to 48, 50 to 77, 79, 80, 82 to 86, 88 to 91, or 92 formulated according to the method described in Formulation Example 6 The mixture was mixed with water to 200 ppm, and the mixture was foliage-sprayed to adhere well to the leaf surface of the soybean. After spraying, the soybeans were air-dried, and 4 days later, they were spray-inoculated with a water suspension containing spores of soybean rust. After inoculation, soybeans were placed in a greenhouse at daytime 23 ° C. and nighttime at 20 ° C. under high humidity for 1 day, and then grown for 10 days in a greenhouse, and then the lesion area was examined. As a result, as for the lesion area in the soybean which processed this-invention compound 1, 3-16, 18-33, 35-48, 50-77, 79, 80, 82-86, 88-91 or 92, all are none. It was less than 30% of the lesion area in treated soybean.

試験例5 コムギ葉枯病(Septoria tritici)に対する防除試験
プラスチックポットに土壌を詰め、そこにコムギ(品種;アポジー)を播種し、温室内で10日間栽培した。製剤例6に記載の方法に準じて製剤化された本発明化合物1、3〜8、10、13〜24、29、30、32〜35、39、40、42、44、49、51、52、54〜58、60、62〜69、71、74、77、79〜82、84〜86、88又は89を濃度が500ppmとなるように水と混合し、該混合物を、上記コムギの葉面に充分付着するように茎葉散布した。散布後コムギを風乾し、4日後にコムギ葉枯病菌の胞子を含む水懸濁液を噴霧接種した。接種後コムギを18℃多湿下に3日間置き、次に照明下で14日から18日間栽培した後、病斑面積を調査した。その結果、本発明化合物1、3〜8、10、13〜24、29、30、32〜35、39、40、42、44、49、51、52、54〜58、60、62〜69、71、74、77、79〜82、84〜86、88又は89を処理したコムギにおける病斑面積はいずれも、無処理のコムギにおける病斑面積の30%以下であった。
Test Example 5 Control Test for Wheat Leaf Blight (Septoria tritici) A soil was packed in a plastic pot, and wheat (variety; apodie) was sown and cultivated in a greenhouse for 10 days. Invention compounds 1, 3 to 8, 10, 13 to 24, 29, 30, 32 to 35, 39, 40, 42, 44, 49, 51, 52 formulated according to the method described in Formulation Example 6. , 54-58, 60, 62-69, 71, 74, 77, 79-82, 84-86, 88 or 89 with water to a concentration of 500 ppm, the mixture being the leaf surface of the wheat The leaves and leaves were sprayed so as to adhere well to the After spraying, the wheat was air-dried, and 4 days later, it was spray-inoculated with an aqueous suspension containing spores of wheat leaf blight. After inoculation, wheat was placed at 18 ° C. for 3 days and then grown under illumination for 14 to 18 days, and then the lesion area was examined. As a result, the compounds of the present invention 1, 3 to 8, 10, 13 to 24, 29, 30, 32 to 35, 39, 40, 42, 44, 49, 51, 52, 54 to 58, 60, 62 to 69, The lesion area in wheat treated with 71, 74, 77, 79 to 82, 84 to 86, 88 or 89 was 30% or less of the lesion area in untreated wheat.

試験例6 コムギ葉枯病(Septoria tritici)に対する防除試験
プラスチックポットに土壌を詰め、そこにコムギ(品種;アポジー)を播種し、温室内で10日間栽培した。製剤例6に記載の方法に準じて製剤化された本発明化合物1、3〜8、11〜14、16〜31、35〜37、39〜44、52〜56、58、60〜62、64〜71、74、77、79〜88又は89を濃度が200ppmとなるように水と混合し、該混合物を、上記コムギの葉面に充分付着するように茎葉散布した。散布後コムギを風乾し、4日後にコムギ葉枯病菌の胞子を含む水懸濁液を噴霧接種した。接種後コムギを18℃多湿下に3日間置き、次に照明下で14日から18日間栽培した後、病斑面積を調査した。その結果、本発明化合物1、3〜8、11〜14、16〜31、35〜37、39〜44、52〜56、58、60〜62、64〜71、74、77、79〜88又は89を処理したコムギにおける病斑面積はいずれも、無処理のコムギにおける病斑面積の30%以下であった。
Test Example 6 Control Test for Wheat Leaf Blight (Septoria tritici) A soil was packed in a plastic pot, and wheat (variety; apodie) was sown and cultivated in a greenhouse for 10 days. Invention compounds 1, 3 to 8, 11 to 14, 16 to 31, 35 to 37, 39 to 44, 52 to 56, 58, 60 to 62, 64 formulated according to the method described in Formulation Example 6. ~ 71, 74, 77, 79-88 or 89 were mixed with water to a concentration of 200 ppm, and the mixture was sprayed with stem and leaf so as to adhere well to the leaf surface of the wheat. After spraying, the wheat was air-dried, and 4 days later, it was spray-inoculated with an aqueous suspension containing spores of wheat leaf blight. After inoculation, wheat was placed at 18 ° C. for 3 days and then grown under illumination for 14 to 18 days, and then the lesion area was examined. As a result, the compounds of the present invention 1, 3 to 8, 11 to 14, 16 to 31, 35 to 37, 39 to 44, 52 to 56, 58, 60 to 62, 64-71, 74, 77, 79 to 88 or The lesion area in each of the 89-treated wheat was 30% or less of that in the untreated wheat.

試験例7 コムギさび病(Puccinia recondita)に対する防除試験
プラスチックポットに土壌を詰め、そこにコムギ(品種;シロガネ)を播種し、温室内で9日間栽培した。製剤例6に記載の方法に準じて製剤化された本発明化合物1〜8、11、13〜25、27、29〜36、39、40、47〜50、52〜69、71、74、77、79、80〜86、88又は89を濃度が500ppmとなるように水と混合し、該混合物を、上記コムギの葉面に充分付着するように茎葉散布した。散布後コムギを風乾し、20℃、照明下で5日間栽培した後、コムギさび病菌の胞子をふりかけ接種した。接種後コムギを23℃、暗黒多湿下に1日間置いた後、20℃、照明下で8日間栽培し、病斑面積を調査した。その結果、本発明化合物1〜8、11、13〜25、27、29〜36、39、40、47〜50、52〜69、71、74、77、79、80〜86、88又は89を処理したコムギにおける病斑面積はいずれも、無処理のコムギにおける病斑面積の30%以下であった。
Test Example 7 Control Test for Wheat Rust (Puccinia recondita) A soil was packed in a plastic pot, and wheat (variety; Shirogane) was sown and cultivated in a greenhouse for 9 days. Invention compounds 1 to 8, 11, 13 to 25, 27, 29 to 36, 39, 40, 47 to 50, 52 to 69, 71, 74, 77 formulated according to the method described in Formulation Example 6. 79, 80 to 86, 88 or 89 were mixed with water to a concentration of 500 ppm, and the mixture was foliated to sufficiently adhere to the leaf surface of the wheat. After spraying, the wheat was air-dried, cultivated at 20 ° C. under illumination for 5 days, and then inoculated with spores of wheat rust fungus. After inoculation, wheat was placed at 23 ° C. in dark and humid for 1 day, and then grown at 20 ° C. in illumination for 8 days, and the lesion area was examined. As a result, the present compounds 1 to 8, 11, 13 to 25, 27, 29 to 36, 39, 40, 47 to 50, 52 to 69, 71, 74, 77, 79, 80 to 86, 88 or 89 can be obtained. The lesion area in the treated wheat was 30% or less of the lesion area in the untreated wheat.

試験例8 コムギさび病(Puccinia recondita)に対する防除試験
プラスチックポットに土壌を詰め、そこにコムギ(品種;シロガネ)を播種し、温室内で9日間栽培した。製剤例6に記載の方法に準じて製剤化された本発明化合物1、3〜8、12〜14、16〜25、29、30、33、35〜37、39〜41、43、44、51、53、55〜58、60〜66、71〜74、77、79〜88又は89を濃度が200ppmとなるように水と混合し、該混合物を、上記コムギの葉面に充分付着するように茎葉散布した。散布後コムギを風乾し、20℃、照明下で5日間栽培した後、コムギさび病菌の胞子をふりかけ接種した。接種後コムギを23℃、暗黒多湿下に1日間置いた後、20℃、照明下で8日間栽培し、病斑面積を調査した。その結果、本発明化合物1、3〜8、12〜14、16〜25、29、30、33、35〜37、39〜41、43、44、51、53、55〜58、60〜66、71〜74、77、79〜88又は89を処理したコムギにおける病斑面積はいずれも、無処理のコムギにおける病斑面積の30%以下であった。
Test Example 8 Control Test for Wheat Rust (Puccinia recondita) A soil was packed in a plastic pot, and wheat (variety; white ginseng) was sown and cultivated in a greenhouse for 9 days. Invention compounds 1, 3 to 8, 12 to 14, 16 to 25, 29, 30, 33, 35 to 37, 39 to 41, 43, 44, 51 formulated according to the method described in Formulation Example 6. 53, 55 to 58, 60 to 66, 71 to 74, 77, 79 to 88 or 89 are mixed with water to a concentration of 200 ppm, and the mixture is sufficiently adhered to the leaf surface of the wheat. The leaves were sprayed. After spraying, the wheat was air-dried, cultivated at 20 ° C. under illumination for 5 days, and then inoculated with spores of wheat rust fungus. After inoculation, wheat was placed at 23 ° C. in dark and humid for 1 day, and then grown at 20 ° C. in illumination for 8 days, and the lesion area was examined. As a result, the compounds of the present invention 1, 3 to 8, 12 to 14, 16 to 25, 29, 30, 33, 35, 37, 39 to 41, 43, 44, 51, 53, 55 to 58, 60 to 66, The lesion area in each of the wheats treated with 71 to 74, 77, 79 to 88, or 89 was 30% or less of the lesion area in untreated wheat.

試験例9 イネいもち病(Magnaporthe grisea)に対する防除試験
プラスチックポットに土壌を詰め、そこにイネ(品種;ヒノヒカリ)を播種し、温室内で20日間栽培した。その後、製剤例6に記載の方法に準じて製剤化された本発明化合物1〜4、6、7、14、17、21、39、51、63、66〜68、71又は82を濃度が500ppmとなるように水と混合し、該混合物を、上記イネの葉面に充分付着するように茎葉散布した。散布後、イネを風乾し、昼間24℃、夜間20℃多湿下で、前記散布処理をしたイネと、イネいもち病菌に罹病したイネ苗(品種;ヒノヒカリ)とを接触させながら6日間置いた後、病斑面積を調査した。その結果、本発明化合物1〜4、6、7、14、17、21、39、51、63、66〜68、71又は82を処理したイネにおける病斑面積はいずれも、無処理のイネにおける病斑面積の30%以下であった。
Test Example 9 Control Test for Rice Blast (Magnaporthe grisea) The soil was packed in a plastic pot, and rice (variety; Hinohikari) was sown and cultivated in a greenhouse for 20 days. Thereafter, the compound of the present invention 1 to 4, 6, 7, 14, 17, 21, 21, 39, 51, 63, 66 to 68, 71 or 82 formulated according to the method described in Formulation Example 6 has a concentration of 500 ppm The mixture was mixed with water so as to give a mixture of the above-mentioned plants, and the mixture was sprayed with leaves and leaves so as to sufficiently adhere to the above-mentioned rice leaf surface. After spraying, the rice is air-dried and left for 6 days while contacting the sprayed rice and the rice seedling infected with rice blast fungus (cultivar: Hinohikari) in the daytime at 24 ° C and nightly at 20 ° C with high humidity. The lesion area was investigated. As a result, the lesion area in the rice treated with the compounds of the present invention 1 to 4, 6, 7, 14, 17, 21, 39, 51, 63, 66 to 68, 71 or 82 in any untreated rice. Less than 30% of the lesion area.

試験例10 イネいもち病(Magnaporthe grisea)に対する防除試験
プラスチックポットに土壌を詰め、そこにイネ(品種;ヒノヒカリ)を播種し、温室内で20日間栽培した。その後、製剤例6に記載の方法に準じて製剤化された本発明化合物3、4、15、20、52、55、63、66〜69又は71を濃度が200ppmとなるように水と混合し、該混合物を、上記イネの葉面に充分付着するように茎葉散布した。散布後、イネを風乾し、昼間24℃、夜間20℃多湿下で、前記散布処理をしたイネと、イネいもち病菌に罹病したイネ苗(品種;ヒノヒカリ)とを接触させながら6日間置いた後、病斑面積を調査した。その結果、本発明化合物3、4、15、20、52、55、63、66〜69又は71を処理したイネにおける病斑面積はいずれも、無処理のイネにおける病斑面積の30%以下であった。
Test Example 10 Control Test for Rice Blast (Magnaporthe grisea) A soil was packed in a plastic pot, and rice (variety; Hinohikari) was sown and cultivated in a greenhouse for 20 days. Thereafter, the present compound 3, 4, 15, 20, 52, 55, 63, 66 to 69 or 71 formulated according to the method described in Formulation Example 6 is mixed with water to a concentration of 200 ppm. The mixture was foliated to sufficiently adhere to the leaf surface of the above rice. After spraying, the rice is air-dried and left for 6 days while contacting the sprayed rice and the rice seedling infected with rice blast fungus (cultivar: Hinohikari) in the daytime at 24 ° C and nightly at 20 ° C with high humidity. The lesion area was investigated. As a result, the lesion area in rice treated with the compound of the present invention 3, 4, 15, 20, 52, 55, 63, 66 to 69 or 71 is 30% or less of the lesion area in untreated rice. there were.

試験例11 キュウリうどんこ病(Sphaerotheca fuliginea)に対する防除試験
プラスチックポットに土壌を詰め、そこにキュウリ(品種;相模半白)を播種し、温室内で12日間栽培した。その後、製剤例6に記載の方法に準じて製剤化された本発明化合物4又は43を濃度が200ppmとなるように水と混合し、該混合物を、上記キュウリの葉面に充分付着するように茎葉散布した。散布後キュウリを風乾し、昼間24℃、夜間20℃の温室に1日間置いた後、キュウリうどんこ病菌に罹病したキュウリ苗(品種;相模半白)の胞子をふりかけ接種した。キュウリを昼間24℃、夜間20℃の温室に8日間栽培した後、病斑面積を調査した。その結果、本発明化合物4又は43を処理したキュウリにおける病斑面積は、無処理のキュウリにおける病斑面積の30%以下であった。
Test Example 11 Control Test against Cucumber Powdery Mildew (Sphaerotheca fuliginea) A plastic pot was filled with soil, and a cucumber (variety; Sagami Hankaku) was sown and cultivated in a greenhouse for 12 days. Thereafter, the compound of the present invention 4 or 43 formulated according to the method described in Formulation Example 6 is mixed with water to a concentration of 200 ppm, and the mixture is sufficiently adhered to the leaf surface of the cucumber. The leaves were sprayed. After spraying, the cucumbers were air-dried and placed in a greenhouse at daytime 24 ° C. and nighttime at 20 ° C. for 1 day, and then sporulated with spores of cucumber seedlings (variety; Sagami Hankaku) infected with cucumber powdery mildew. The cucumber was grown in a greenhouse at 24 ° C. in the daytime and at 20 ° C. in the night for 8 days, and then the lesion area was examined. As a result, the lesion area in the cucumber treated with the compound of the present invention 4 or 43 was 30% or less of the lesion area in the untreated cucumber.

試験例12 オオムギ網斑病(Pyrenophora teres)に対する防除試験
プラスチックポットに土壌を詰め、そこにオオムギ(品種;ニシノホシ)を播種し、温室で7日間栽培した。製剤例6に記載の方法に準じて製剤化された本発明化合物5、8、10、15、32、50、55、61又は71を、濃度が500ppmとなるように水と混合し、該混合物を、上記オオムギの葉面に充分付着するように茎葉散布した。散布後オオムギを風乾し、2日後にオオムギ網斑病菌胞子の水懸濁液を噴霧接種した。接種後オオムギを昼間23℃、夜間20℃の温室内で多湿下に3日間置き、次に温室内で7日間栽培した後、病斑面積を調査した。その結果、本発明化合物5、8、10、15、32、50、55、61又は71を処理したオオムギにおける病斑面積は、無処理のオオムギにおける病斑面積の30%以下であった。
Test Example 12 Control Test Against Barley Blotch (Pyrenophora teres) The soil was packed in a plastic pot, and barley (variety: Nishinohoshi) was sown and cultivated in a greenhouse for 7 days. The compound of the present invention 5, 8, 10, 15, 32, 50, 55, 61 or 71 formulated according to the method described in Formulation Example 6 is mixed with water to a concentration of 500 ppm, and the mixture Were sprayed so as to adhere sufficiently to the above-mentioned barley leaf surface. After spraying, the barley was air-dried, and two days later, it was spray-inoculated with an aqueous suspension of barley net blotch spores. After inoculation, barley was placed in a greenhouse at 23 ° C. and 20 ° C. at night under humid conditions for 3 days, and then grown for 7 days in a greenhouse, and then the lesion area was examined. As a result, the lesion area in the barley treated with the compound 5, 8, 10, 15, 32, 50, 55, 61 or 71 of the present invention was 30% or less of the lesion area in untreated barley.

試験例13
容器に植えたキュウリ苗(第2本葉展開期)にワタアブラムシ(Aphis gossypii、全ステージ)約30頭を接種し、1日間静置した。製剤例6に記載の方法に準じて製剤化された本発明化合物15、64、84又は85を、濃度が500ppmとなるように水で調整し、該調整液を、上記苗に10mL/苗の割合で散布した。更に5日後、生存虫数を調査し、以下の式により防除価を求めた。
防除価(%)={1−(Cb×Tai)/(Cai×Tb)}×100
なお、式中の文字は以下の意味を表す。
Cb:無処理区の供試虫数
Cai:無処理区の調査時の生存虫数
Tb:処理区の供試虫数
Tai:処理区の調査時の生存虫数
ここで無処理区とは、本発明化合物を使用しないこと以外は処理区と同じ操作をする区を意味する。
その結果、本発明化合物15、64、84又は85の処理区は、防除価90%以上を示した。
Test Example 13
About 30 cotton aphids (Aphis gossypii, all stages) were inoculated to cucumber seedlings (the second true leaf development stage) planted in a container and allowed to stand for 1 day. The compound of the present invention 15, 64, 84 or 85 formulated according to the method described in Formulation Example 6 is adjusted with water to a concentration of 500 ppm, and the solution is adjusted to 10 mL / seedling of the above-mentioned seedlings Sprayed at a rate. After 5 days, the number of surviving insects was examined, and the control value was determined by the following equation.
Control value (%) = {1- (Cb × Tai) / (Cai × Tb)} × 100
The letters in the formula have the following meanings.
Cb: Number of tested insects in untreated area Cai: Number of surviving insects in survey in untreated area Tb: Number of tested insects in treated zone Tai: Number of surviving insects in survey in treated area Here, untreated group means It means a zone that performs the same operation as the treatment zone except that the compound of the present invention is not used.
As a result, the treated area of the compound of the present invention 15, 64, 84 or 85 showed a control value of 90% or more.

比較試験例 コムギさび病(Puccinia recondita)に対する防除試験
プラスチックポットに土壌を詰め、そこにコムギ(品種;シロガネ)を播種し、温室内で9日間栽培した。製剤例6に記載の方法に準じて製剤化された、国際公開第2013/008162号に記載のN,N−ジメチル−4−[5−(トリフルオロメチル)−1,2,4−オキサジアゾール−3−イル]ベンゼンスルホンアミドを濃度が200ppmとなるように水と混合し、該混合物を、上記コムギの葉面に充分付着するように茎葉散布した。散布後コムギを風乾し、20℃、照明下で5日間栽培した後、コムギさび病菌の胞子をふりかけ接種した。接種後コムギを23℃、暗黒多湿下に1日間置いた後、20℃、照明下で8日間栽培し、病斑面積を調査した。その結果、N,N−ジメチル−4−[5−(トリフルオロメチル)−1,2,4−オキサジアゾール−3−イル]ベンゼンスルホンアミドを処理したコムギにおける病斑面積はいずれも、無処理のコムギにおける病斑面積の70%以上であった。
Comparative Test Example Control Test for Wheat Rust (Puccinia recondita) The soil was packed in a plastic pot, and wheat (variety; Shirogane) was sown and cultivated in a greenhouse for 9 days. N, N-Dimethyl-4- [5- (trifluoromethyl) -1,2,4-oxadi, described in WO 2013/008162, formulated according to the method described in Formulation Example 6 Azole-3-yl] benzenesulfonamide was mixed with water to a concentration of 200 ppm, and the mixture was foliage sprayed to adhere well to the wheat leaf surface. After spraying, the wheat was air-dried, cultivated at 20 ° C. under illumination for 5 days, and then inoculated with spores of wheat rust fungus. After inoculation, wheat was placed at 23 ° C. in dark and humid for 1 day, and then grown at 20 ° C. in illumination for 8 days, and the lesion area was examined. As a result, no lesion area was found in wheat treated with N, N-dimethyl-4- [5- (trifluoromethyl) -1,2,4-oxadiazol-3-yl] benzenesulfonamide. More than 70% of the lesion area in the treated wheat.

本発明化合物は、有害生物に対して防除効力を有し、有害生物防除剤の有効成分として有用である。   The compound of the present invention has pesticidal activity against pests and is useful as an active ingredient of pest control agents.

Claims (11)

式(I)
Figure 2019089711
〔式中、
Aは、単結合、NR1又は酸素原子を表し、
mは、0〜3のいずれかを表し、
1は、1以上のハロゲン原子を有していてもよいC1−C6アルキル基又は水素原子を表し、
Xは、単結合、CR45、NR6又は酸素原子を表し、
2、R3、R4及びR5は、各々独立して、群Aより選ばれる1以上の置換基を有していてもよいC1−C6アルキル基、群Bより選ばれる1以上の置換基を有していてもよいC1−C6アルコキシ基、群Dより選ばれる1以上の置換基を有していてもよいフェニル基、群Dより選ばれる1以上の置換基を有していてもよいピリジル基、群Dより選ばれる1以上の置換基を有していてもよいC3−C6シクロアルキル基、水素原子、ハロゲン原子、若しくはシアノ基を表すか、又はR2及びR3は、それらが結合する炭素原子と一緒になって3−6員環を形成していてもよく(該3−6員環は群Dより選ばれる1以上の置換基を有していてもよい)、mが2又は3である場合、複数のR2及びR3は同一でも異なっていてもよく、
6は、群Aより選ばれる1以上の置換基を有していてもよいC1−C6アルキル基、1以上のハロゲン原子を有していてもよいC3−C6アルケニル基、1以上のハロゲン原子を有していてもよいC3−C6アルキニル基、1以上のハロゲン原子を有していてもよいC1−C6アルコキシ基、群Dより選ばれる1以上の置換基を有していてもよいC3−C6シクロアルキル基、群Dより選ばれる1以上の置換基を有していてもよいフェニル基、群Dより選ばれる1以上の置換基を有していてもよい5員芳香族ヘテロ環基、群Dより選ばれる1以上の置換基を有していてもよい6員芳香族ヘテロ環基又は水素原子を表し、
nは、0、1又は2を表し、
Qは、酸素原子、NR7、N−CN、N−NO2、N−C(O)R7、N−C(O)OR7又はN−S(O)27を表し(nが2の場合、2つのQは同一でも異なっていてもよい)
7は、ハロゲン原子及びシアノ基からなる群より選ばれる1以上の置換基を有していてもよいC1−C6アルキル基又は水素原子を表し、
Gは、チオフェン環、フラン環、イミダゾール環、オキサゾール環、イソオキサゾール環、チアゾール環、オキサジアゾール環、チアジアゾール環、ピリジン環、ピラジン環、ピリダジン環、ピリミジン環又はベンゼン環{該チオフェン環、該フラン環、該イミダゾール環、該オキサゾール環、該イソオキサゾール環、該チアゾール環、該ピリジン環、該ピラジン環、該ピリダジン環、及び該ピリミジン環は、群Dより選ばれる1以上の置換基を有していてもよい。また、nが0の場合、該ベンゼン環は群Iより選ばれる1以上の置換基を有していてもよく、nが1又は2の場合、該ベンゼン環は群Dより選ばれる1以上の置換基を有していてもよい}を表し、
Yは、群Dより選ばれる1以上の置換基を有していてもよいC3−C6シクロアルキル基、群Dより選ばれる1以上の置換基を有していてもよいフェニル基、群Dより選ばれる1以上の置換基を有していてもよい5員芳香族ヘテロ環基、群Gより選ばれる1以上の置換基を有していてもよい6員芳香族ヘテロ環基、群Dより選ばれる1以上の置換基を有していてもよい3−6員非芳香族ヘテロ環基、CR8910、NR1112又はOR13を表し、
8、R9及びR10は、各々独立して、群A及び群Fからなる群より選ばれる1以上の置換基を有していてもよいC1−C6アルキル基、1以上のハロゲン原子を有していてもよいC3−C6アルケニル基、1以上のハロゲン原子を有していてもよいC3−C6アルキニル基、群Bより選ばれる1以上の置換基を有していてもよいC1−C6アルコキシ基、群Dより選ばれる1以上の置換基を有していてもよいC3−C6シクロアルキル基、群Dより選ばれる1以上の置換基を有していてもよいフェニル基、群Dより選ばれる1以上の置換基を有していてもよい5−6員芳香族ヘテロ環基、水素原子、ハロゲン原子又はシアノ基を表し、
11及びR12は、各々独立して、群E及び群Fからなる群より選ばれる1以上の置換基を有していてもよいC1−C6アルキル基、1以上のハロゲン原子を有していてもよいC3−C6アルケニル基、1以上のハロゲン原子を有していてもよいC3−C6アルキニル基、1以上のハロゲン原子を有していてもよいC1−C6アルコキシ基、群Dより選ばれる1以上の置換基を有していてもよいC3−C6シクロアルキル基、群Dより選ばれる1以上の置換基を有していてもよいフェニル基、群Dより選ばれる1以上の置換基を有していてもよい5−6員芳香族ヘテロ環基若しくは水素原子を表すか、又はR11とR12とは、互いに結合して3−8員ヘテロ環(該3−8員ヘテロ環は群Dより選ばれる1以上の置換基を有していてもよい)を形成していてもよく、
13は、群A及び群Fからなる群より選ばれる1以上の置換基を有していてもよいC1−C6アルキル基、1以上のハロゲン原子を有していてもよいC3−C6アルケニル基、1以上のハロゲン原子を有していてもよいC3−C6アルキニル基、群Dより選ばれる1以上の置換基を有していてもよいC3−C6シクロアルキル基、群Dより選ばれる1以上の置換基を有していてもよいフェニル基、群Dより選ばれる1以上の置換基を有していてもよい5−6員芳香族ヘテロ環基又は水素原子を表し、
XがCR45であり、YがCR8910である場合、R4とR8とは、互いに結合して5−7員ヘテロ環を形成していてもよく(該5−7員ヘテロ環は群Dより選ばれる1以上の置換基を有していてもよい)、
XがCR45であり、YがNR1112である場合、R4とR11とは、互いに結合して5−7員ヘテロ環を形成していてもよく(該5−7員ヘテロ環は群Dより選ばれる1以上の置換基を有していてもよい)、
XがCR45であり、Yが、OR13である場合、R4とR13とは、互いに結合して5−7員ヘテロ環を形成していてもよく(該5−7員ヘテロ環は群Dより選ばれる1以上の置換基を有していてもよい)、
XがNR6であり、YがCR8910である場合、R6とR8とは、互いに結合して5−7員ヘテロ環を形成していてもよく(該5−7員ヘテロ環は群Dより選ばれる1以上の置換基を有していてもよい)、
XがNR6であり、YがNR1112である場合、R6とR11とは、互いに結合して5−7員ヘテロ環を形成していてもよく(該5−7員ヘテロ環は群Dより選ばれる1以上の置換基を有していてもよい)、
XがNR6であり、Yが、OR13である場合、R6とR13とは、互いに結合して5−7員ヘテロ環を形成していてもよい(該5−7員ヘテロ環は群Dより選ばれる1以上の置換基を有していてもよい)。
群A:1以上のハロゲン原子を有していてもよいC1−C6アルコキシ基、1以上のハロゲン原子を有していてもよいC1−C6アルキルチオ基、群Cより選ばれる1以上の置換基を有していてもよいC3−C6シクロアルキル基、群Hより選ばれる1以上の置換基を有していてもよいフェニル基、群Hより選ばれる1以上の置換基を有していてもよい5−6員芳香族ヘテロ環基、ハロゲン原子、ニトロ基及びシアノ基からなる群。
群B:1以上のハロゲン原子を有していてもよいC1−C6アルキルチオ基、群Hより選ばれる1以上の置換基を有していてもよいフェニル基、群Hより選ばれる1以上の置換基を有していてもよい5−6員芳香族ヘテロ環基、ハロゲン原子、ニトロ基及びシアノ基からなる群。
群C:ハロゲン原子、ニトロ基、及びシアノ基からなる群。
群D:群Cより選ばれる1以上の置換基を有していてもよいC1−C6アルキル基、群Cより選ばれる1以上の置換基を有していてもよいC3−C6シクロアルキル基、1以上のハロゲン原子を有していてもよいC1−C6アルコキシ基、1以上のハロゲン原子を有していてもよいC3−C6アルケニルオキシ基、1以上のハロゲン原子を有していてもよいC3−C6アルキニルオキシ基、1以上のハロゲン原子を有していてもよいC1−C6アルキルチオ基、1以上のハロゲン原子を有していてもよいC1−C6アルキルスルホニルオキシ基、ハロゲン原子、シアノ基、及びニトロ基からなる群。
群E:群Cより選ばれる1以上の置換基を有していてもよいC3−C6シクロアルキル基、1以上のハロゲン原子を有していてもよいC1−C6アルコキシ基、1以上のハロゲン原子を有していてもよいC1−C6アルキルチオ基、群Hより選ばれる1以上の置換基を有していてもよいフェニル基、群Hより選ばれる1以上の置換基を有していてもよい5−6員芳香族ヘテロ環基、1以上のハロゲン原子を有していてもよいC1−C6アルキルスルホニル基、1以上のハロゲン原子を有していてもよいC1−C6アルキルスルホニルオキシ基及びハロゲン原子からなる群。
群F:群Cより選ばれる1以上の置換基を有していてもよいC2−C7アルキルカルボニルアミノ基、群Cより選ばれる1以上の置換基を有していてもよいC1−C6アルキルアミノカルボニル基、群Cより選ばれる1以上の置換基を有していてもよいジ(C1−C6アルキル)アミノカルボニル基、群Cより選ばれる1以上の置換基を有していてもよいC1−C6アルキルスルホニルアミノ基、群Cより選ばれる1以上の置換基を有していてもよいC1−C6アルキルアミノスルホニル基及び群Cより選ばれる1以上の置換基を有していてもよいジ(C1−C6アルキル)アミノスルホニル基からなる群。
群G:群Cより選ばれる1以上の置換基を有していてもよいC1−C6アルキル基、群Cより選ばれる1以上の置換基を有していてもよいC3−C6シクロアルキル基、1以上のハロゲン原子を有していてもよいC1−C6アルコキシ基、1以上のハロゲン原子を有していてもよいC3−C6アルケニルオキシ基、1以上のハロゲン原子を有していてもよいC3−C6アルキニルオキシ基、1以上のハロゲン原子を有していてもよいC1−C6アルキルチオ基、1以上のハロゲン原子を有していてもよいC1−C6アルキルスルホニルオキシ基、ハロゲン原子、及びニトロ基からなる群。
群H:1以上のハロゲン原子を有していてもよいC1−C6アルキル基、1以上のハロゲン原子を有していてもよいC1−C6アルコキシ基、ハロゲン原子及びシアノ基からなる群。
群I:群Cより選ばれる1以上の置換基を有していてもよいC1−C6アルキル基、群Cより選ばれる1以上の置換基を有していてもよいC3−C6シクロアルキル基、1以上のハロゲン原子を有していてもよいC3−C6アルケニルオキシ基、1以上のハロゲン原子を有していてもよいC3−C6アルキニルオキシ基、1以上のハロゲン原子を有していてもよいC1−C6アルキルチオ基、1以上のハロゲン原子を有していてもよいC1−C6アルキルスルホニルオキシ基、フッ素原子及びシアノ基からなる群。〕
で示される化合物。
Formula (I)
Figure 2019089711
[In the formula,
A represents a single bond, NR 1 or an oxygen atom,
m represents any of 0 to 3;
R 1 represents a C1-C6 alkyl group optionally having one or more halogen atoms or a hydrogen atom,
X represents a single bond, CR 4 R 5 , NR 6 or an oxygen atom,
R 2 , R 3 , R 4 and R 5 are each independently a C 1 -C 6 alkyl group optionally having one or more substituents selected from group A, one or more substituents selected from group B A C1-C6 alkoxy group which may have a group, a phenyl group which may have one or more substituents selected from group D, and one or more substituents selected from group D A pyridyl group, a C3-C6 cycloalkyl group optionally having one or more substituents selected from group D, a hydrogen atom, a halogen atom, or a cyano group, or R 2 and R 3 M may be taken together with the carbon atom to which it is attached to form a 3- to 6-membered ring (the 3- to 6-membered ring may have one or more substituents selected from Group D), m When is 2 or 3, the plurality of R 2 and R 3 may be the same or different,
R 6 is a C 1 -C 6 alkyl group which may have one or more substituents selected from group A, a C 3 -C 6 alkenyl group which may have one or more halogen atoms, one or more halogen atoms C 3 -C 6 alkynyl group which may have one or more substituents, C 1 -C 6 alkoxy group which may have one or more halogen atoms, C 3-which may have one or more substituents selected from group D A C6 cycloalkyl group, a phenyl group optionally having one or more substituents selected from group D, a 5-membered aromatic heterocyclic group optionally having one or more substituents selected from group D, A 6-membered aromatic heterocyclic group or a hydrogen atom which may have one or more substituents selected from group D,
n represents 0, 1 or 2;
Q represents an oxygen atom, NR 7 , N-CN, N-NO 2 , N-C (O) R 7 , N-C (O) OR 7 or N-S (O) 2 R 7 (n is In the case of 2, two Q may be the same or different)
R 7 represents a C 1 -C 6 alkyl group optionally having one or more substituents selected from the group consisting of a halogen atom and a cyano group, or a hydrogen atom,
G is a thiophene ring, furan ring, imidazole ring, oxazole ring, isoxazole ring, thiazole ring, oxadiazole ring, thiadiazole ring, pyridine ring, pyrazine ring, pyridazine ring, pyrimidine ring or benzene ring {the thiophene ring, The furan ring, the imidazole ring, the oxazole ring, the isoxazole ring, the thiazole ring, the pyridine ring, the pyrazine ring, the pyridazine ring, and the pyrimidine ring have one or more substituents selected from group D. It may be done. In addition, when n is 0, the benzene ring may have one or more substituents selected from group I. When n is 1 or 2, the benzene ring is one or more selected from group D. Represents an optionally substituted substituent},
Y is a C3-C6 cycloalkyl group optionally having one or more substituents selected from group D, a phenyl group optionally having one or more substituents selected from group D, a group D 5-membered aromatic heterocyclic group optionally having one or more substituents selected, 6-membered aromatic heterocyclic group optionally having one or more substituents selected from group G, from group D Represents a 3- to 6-membered non-aromatic heterocyclic group optionally having one or more substituents, CR 8 R 9 R 10 , NR 11 R 12 or OR 13 ,
R 8 , R 9 and R 10 each independently represent a C1-C6 alkyl group optionally having one or more substituents selected from the group consisting of Group A and Group F, and one or more halogen atoms C3-C6 alkenyl group which may have, C3-C6 alkynyl group which may have one or more halogen atoms, C1-C6 which may have one or more substituents selected from group B Alkoxy group, C3-C6 cycloalkyl group optionally having one or more substituents selected from group D, phenyl group optionally having one or more substituents selected from group D, group D Represents a 5- to 6-membered aromatic heterocyclic group optionally having one or more substituents, a hydrogen atom, a halogen atom or a cyano group,
R 11 and R 12 each independently have a C 1 -C 6 alkyl group optionally having one or more substituents selected from the group consisting of Group E and Group F, and one or more halogen atoms A C3-C6 alkenyl group which may be, a C3-C6 alkynyl group which may have one or more halogen atoms, a C1-C6 alkoxy group which may have one or more halogen atoms, a group D C3-C6 cycloalkyl group which may have one or more substituents, phenyl group which may have one or more substituents selected from group D, one or more substituents selected from group D Represents a 5- to 6-membered aromatic heterocyclic group or hydrogen atom which may be possessed, or R 11 and R 12 are bonded to each other to form a 3- to 8-membered heterocyclic ring (the 3- to 8-membered heterocyclic ring is Form one or more substituents selected from group D) Even if well,
R 13 is a C1-C6 alkyl group optionally having one or more substituents selected from the group consisting of Group A and Group F, and a C3-C6 alkenyl group optionally having one or more halogen atoms A C3-C6 alkynyl group optionally having one or more halogen atoms, a C3-C6 cycloalkyl group optionally having one or more substituents selected from group D, one or more selected from group D Or a substituted or unsubstituted phenyl group, a 5-6 membered aromatic heterocyclic group optionally having one or more substituents selected from group D, or a hydrogen atom,
When X is CR 4 R 5 and Y is CR 8 R 9 R 10 , R 4 and R 8 may be combined with each other to form a 5-7 membered heterocyclic ring (the 7-membered heterocyclic ring may have one or more substituents selected from group D),
When X is CR 4 R 5 and Y is NR 11 R 12 , R 4 and R 11 may be combined with each other to form a 5-7 membered heterocyclic ring (the 5-7 membered member) The heterocycle may have one or more substituents selected from group D),
When X is CR 4 R 5 and Y is OR 13 , R 4 and R 13 may be bonded to each other to form a 5-7 membered hetero ring (the 5-7 membered hetero ring) The ring may have one or more substituents selected from group D),
When X is NR 6 and Y is CR 8 R 9 R 10 , R 6 and R 8 may be combined with each other to form a 5-7 membered heterocyclic ring (the 5-7 membered member) The heterocycle may have one or more substituents selected from group D),
When X is NR 6 and Y is NR 11 R 12 , R 6 and R 11 may be bonded to each other to form a 5- to 7-membered heterocyclic ring (the 5- to 7-membered heterocyclic ring) And may have one or more substituents selected from group D),
When X is NR 6 and Y is OR 13 , R 6 and R 13 may be bonded to each other to form a 5-7 membered heterocycle (the 5-7 membered heterocycle is It may have one or more substituents selected from group D).
Group A: C1-C6 alkoxy group optionally having one or more halogen atoms, C1-C6 alkylthio group optionally having one or more halogen atoms, one or more substituents selected from group C A C3-C6 cycloalkyl group which may have, a phenyl group which may have one or more substituents selected from group H, and one or more substituents selected from group H A group consisting of a 5- to 6-membered aromatic heterocyclic group, a halogen atom, a nitro group and a cyano group.
Group B: C1-C6 alkylthio group optionally having one or more halogen atoms, phenyl group optionally having one or more substituents selected from group H, one or more substituents selected from group H A group comprising a 5- to 6-membered aromatic heterocyclic group which may have a group, a halogen atom, a nitro group and a cyano group.
Group C: a group consisting of a halogen atom, a nitro group, and a cyano group.
Group D: C1-C6 alkyl group optionally having one or more substituents selected from group C, C3-C6 cycloalkyl group optionally having one or more substituents selected from group C, C1-C6 alkoxy group optionally having one or more halogen atoms, C3-C6 alkenyloxy group optionally having one or more halogen atoms, C3 optionally having one or more halogen atoms -C6 alkynyloxy group, C1-C6 alkylthio group optionally having one or more halogen atoms, C1-C6 alkylsulfonyloxy group optionally having one or more halogen atoms, halogen atom, cyano group, And a nitro group.
Group E: C3-C6 cycloalkyl group optionally having one or more substituents selected from group C, C1-C6 alkoxy group optionally having one or more halogen atoms, one or more halogen atoms A C1-C6 alkylthio group which may have one or more substituents, a phenyl group which may have one or more substituents selected from group H, and one or more substituents selected from group H 5-6 membered aromatic heterocyclic group, C1-C6 alkylsulfonyl group optionally having one or more halogen atoms, C1-C6 alkylsulfonyloxy group optionally having one or more halogen atoms, and halogen A group of atoms.
Group F: C2 to C7 alkylcarbonylamino group optionally having one or more substituents selected from group C, C1 to C6 alkylamino optionally having one or more substituents selected from group C A carbonyl group, a di (C 1 -C 6 alkyl) aminocarbonyl group optionally having one or more substituents selected from group C, a C 1-optionally having one or more substituents selected from group C A C6 alkylsulfonylamino group, a C1-C6 alkylaminosulfonyl group optionally having one or more substituents selected from group C, and one or more substituents optionally selected from group C The group which consists of a C1-C6 alkyl) aminosulfonyl group.
Group G: C1-C6 alkyl group optionally having one or more substituents selected from group C, C3-C6 cycloalkyl group optionally having one or more substituents selected from group C, C1-C6 alkoxy group optionally having one or more halogen atoms, C3-C6 alkenyloxy group optionally having one or more halogen atoms, C3 optionally having one or more halogen atoms -C6 alkynyloxy group, C1-C6 alkylthio group optionally having one or more halogen atoms, C1-C6 alkylsulfonyloxy group optionally having one or more halogen atoms, halogen atom, and nitro group A group consisting of
Group H: a group consisting of a C1 to C6 alkyl group optionally having one or more halogen atoms, a C1 to C6 alkoxy group optionally having one or more halogen atoms, a halogen atom and a cyano group.
Group I: C1-C6 alkyl group optionally having one or more substituents selected from group C, C3-C6 cycloalkyl group optionally having one or more substituents selected from group C, C3-C6 alkenyloxy group optionally having one or more halogen atoms, C3-C6 alkynyloxy group optionally having one or more halogen atoms, optionally having one or more halogen atoms A group consisting of a C1-C6 alkylthio group, a C1-C6 alkylsulfonyloxy group optionally having one or more halogen atoms, a fluorine atom and a cyano group. ]
A compound represented by
Aが単結合であり、mが0であり、
Gがベンゼン環又はピリジン環(該ベンゼン環及び該ピリジン環は1以上のフッ素原子を有していてもよい)であり、
Xが単結合又はNR6であり、
Qが酸素原子、NH、N−CN、N−C(O)R7又はN−C(O)OR7であり、
7がC1−C6アルキル基であり、
Yが1以上のハロゲン原子を有していてもよいC3−C6シクロアルキル基、1以上のハロゲン原子を有していてもよいフェニル基、CR8910又はNR1112であり、
6がC1−C6アルキル基(該C1−C6アルキル基は、ハロゲン原子、C1−C6アルコキシ基、C1−C6アルキルチオ基、C3−C6シクロアルキル基及びフェニル基からなる群より選ばれる1以上の置換基を有していてもよい)、1以上のハロゲン原子を有していてもよいC3−C6アルキニル基、1以上のハロゲン原子を有していてもよいC3−C6シクロアルキル基、フェニル基(該フェニル基はハロゲン原子、C1−C6アルキル基又はC1−C6アルコキシ基からなる群より選ばれる1以上の置換基を有していてもよい)又は水素原子であり、
8、R9及びR10が、各々独立して、1以上のハロゲン原子を有していてもよいC1−C6アルキル基、フェニル基、水素原子又はハロゲン原子であり、
11及びR12が、各々独立して、水素原子又はC1−C6アルキル基であり、
Aが、Gにあたるベンゼン環又はピリジン環上で、オキサジアゾール環に対してパラ位に結合している請求項1に記載の化合物。
A is a single bond and m is 0,
G is a benzene ring or a pyridine ring (the benzene ring and the pyridine ring may have one or more fluorine atoms),
X is a single bond or NR 6 ,
Q is an oxygen atom, NH, N-CN, a N-C (O) R 7 or N-C (O) OR 7 ,
R 7 is a C1-C6 alkyl group,
Y is a C3-C6 cycloalkyl group which may have one or more halogen atoms, a phenyl group which may have one or more halogen atoms, CR 8 R 9 R 10 or NR 11 R 12 ,
R 6 is a C 1 -C 6 alkyl group (wherein the C 1 -C 6 alkyl group is one or more selected from the group consisting of a halogen atom, a C 1 -C 6 alkoxy group, a C 1 -C 6 alkylthio group, a C 3 -C 6 cycloalkyl group and a phenyl group Optionally substituted), C3-C6 alkynyl group optionally having one or more halogen atoms, C3-C6 cycloalkyl group optionally having one or more halogen atoms, phenyl group (The phenyl group may have one or more substituents selected from the group consisting of a halogen atom, a C1-C6 alkyl group or a C1-C6 alkoxy group) or a hydrogen atom,
R 8 , R 9 and R 10 each independently represent a C1-C6 alkyl group optionally having one or more halogen atoms, a phenyl group, a hydrogen atom or a halogen atom,
R 11 and R 12 are each independently a hydrogen atom or a C 1 -C 6 alkyl group,
The compound according to claim 1, wherein A is bonded on the benzene ring or pyridine ring corresponding to G in the para-position to the oxadiazole ring.
Aが単結合であり、mが0であり、
Gがベンゼン環又はピリジン環であり(該ベンゼン環及び該ピリジン環は1以上のフッ素原子を有していてもよい)、
Xが単結合又はNR6であり、
Qが酸素原子、NH又はN−CNであり、
Yが1以上のハロゲン原子を有していてもよいC3−C6シクロアルキル基、CR8910又はNR1112であり、
6が1以上のハロゲン原子を有していてもよいC1−C6アルキル基又は水素原子であり、
8、R9及びR10が、各々独立して1以上のハロゲン原子を有していてもよいC1−C6アルキル基又は水素原子であり、
11及びR12が、各々独立してC1−C6アルキル基(該C1−C6アルキル基はハロゲン原子、C3−C6シクロアルキル基及びC1−C6アルコキシ基からなる群より選ばれる1以上の置換基を有していてもよい)、1以上のハロゲン原子を有していてもよいC3−C6アルキニル基、1以上のハロゲン原子を有していてもよいC3−C6シクロアルキル基若しくは水素原子であるか、又はR11とR12とが互いに結合して3−6員ヘテロ環(該3−6員ヘテロ環は1以上のハロゲン原子を有していてもよい)を形成している、
請求項1又は請求項2に記載の化合物。
A is a single bond and m is 0,
G is a benzene ring or a pyridine ring (the benzene ring and the pyridine ring may have one or more fluorine atoms),
X is a single bond or NR 6 ,
Q is an oxygen atom, NH or N-CN,
Y is a C3-C6 cycloalkyl group optionally having one or more halogen atoms, CR 8 R 9 R 10 or NR 11 R 12 ,
R 6 is a C 1 -C 6 alkyl group optionally having one or more halogen atoms, or a hydrogen atom,
R 8 , R 9 and R 10 each independently represent a C1-C6 alkyl group optionally having one or more halogen atoms, or a hydrogen atom,
Each of R 11 and R 12 independently represents a C 1 -C 6 alkyl group (wherein the C 1 -C 6 alkyl group is a halogen atom, a C 3 -C 6 cycloalkyl group, and a C 1 -C 6 alkoxy group) A C3-C6 alkynyl group optionally having one or more halogen atoms, a C3-C6 cycloalkyl group optionally having one or more halogen atoms, or a hydrogen atom Or R 11 and R 12 are bonded to each other to form a 3- to 6-membered heterocyclic ring (the 3- to 6-membered heterocyclic ring may have one or more halogen atoms),
A compound according to claim 1 or claim 2.
Gが1以上のフッ素原子を有していてもよいベンゼン環であり、
Yが1以上のハロゲン原子を有していてもよいC3−C6シクロアルキル基又はCR8910である、
請求項1〜請求項3のいずれかに記載の化合物。
G is a benzene ring which may have one or more fluorine atoms,
Y is a C3-C6 cycloalkyl group optionally having one or more halogen atoms, or CR 8 R 9 R 10 ,
A compound according to any of claims 1 to 3.
Gが1以上のフッ素原子を有していてもよいベンゼン環であり、
Xが単結合であり、
YがCR8910である、
請求項1〜請求項4のいずれかに記載の化合物。
G is a benzene ring which may have one or more fluorine atoms,
X is a single bond,
Y is CR 8 R 9 R 10 ,
The compound as described in any one of Claims 1-4.
Gが1以上のフッ素原子を有していてもよいベンゼン環であり、
XがNR6であり、
nが2であり、
Qが酸素原子であり、
Yが1以上のハロゲン原子を有していてもよいC3−C6シクロアルキル基又はCR8910である、
請求項1〜請求項4のいずれかに記載の化合物。
G is a benzene ring which may have one or more fluorine atoms,
X is NR 6 ,
n is 2 and
Q is an oxygen atom,
Y is a C3-C6 cycloalkyl group optionally having one or more halogen atoms, or CR 8 R 9 R 10 ,
The compound as described in any one of Claims 1-4.
Gが1以上のフッ素原子を有していてもよいベンゼン環であり、
Xが単結合であり、
nが2であり、
Qが酸素原子であり、
YがNR1112である、
請求項1〜請求項3のいずれかに記載の化合物。
G is a benzene ring which may have one or more fluorine atoms,
X is a single bond,
n is 2 and
Q is an oxygen atom,
Y is NR 11 R 12 ,
A compound according to any of claims 1 to 3.
請求項1〜請求項7のいずれかに記載の化合物を含有する有害生物防除剤。 A pest control agent containing the compound according to any one of claims 1 to 7. 請求項1〜請求項7のいずれかに記載の化合物の有効量を植物又は土壌に処理することによる、有害生物の防除方法。 A method for controlling pests by treating plants or soil with an effective amount of the compound according to any one of claims 1 to 7. 有害生物を防除するための、請求項1〜請求項7のいずれかに記載の化合物の使用。 Use of a compound according to any of claims 1 to 7 for controlling pests. 殺菌剤、殺虫剤、殺ダニ剤、殺センチュウ剤、植物成長調節剤及び共力剤からなる群より選ばれる1以上、並びに、請求項1〜請求項7のいずれかに記載の化合物を含有する組成物。 A compound according to any one of claims 1 to 7 which contains one or more selected from the group consisting of fungicides, insecticides, acaricides, nematocides, plant growth regulators and synergists. Composition.
JP2016239161A 2016-06-10 2016-12-09 Oxadiazole compound and application thereof Pending JP2019089711A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
PCT/JP2017/021473 WO2017213252A1 (en) 2016-06-10 2017-06-09 Oxadiazole compound and use as pesticide

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2016115977 2016-06-10
JP2016115977 2016-06-10

Publications (1)

Publication Number Publication Date
JP2019089711A true JP2019089711A (en) 2019-06-13

Family

ID=63667418

Family Applications (1)

Application Number Title Priority Date Filing Date
JP2016239161A Pending JP2019089711A (en) 2016-06-10 2016-12-09 Oxadiazole compound and application thereof

Country Status (2)

Country Link
JP (1) JP2019089711A (en)
AR (1) AR108708A1 (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN110183434A (en) * 2019-06-10 2019-08-30 南京林业大学 A kind of furodiazole compound and its preparation method and application
JP2020516598A (en) * 2017-04-06 2020-06-11 エフ エム シー コーポレーションFmc Corporation Fungicidal oxadiazole

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2020516598A (en) * 2017-04-06 2020-06-11 エフ エム シー コーポレーションFmc Corporation Fungicidal oxadiazole
JP7235672B2 (en) 2017-04-06 2023-03-08 エフ エム シー コーポレーション fungicidal oxadiazole
CN110183434A (en) * 2019-06-10 2019-08-30 南京林业大学 A kind of furodiazole compound and its preparation method and application
CN110183434B (en) * 2019-06-10 2022-07-12 南京林业大学 Oxadiazole compound and preparation method and application thereof

Also Published As

Publication number Publication date
AR108708A1 (en) 2018-09-19

Similar Documents

Publication Publication Date Title
WO2017213252A1 (en) Oxadiazole compound and use as pesticide
JP6756724B2 (en) Pyrazine compounds and their harmful arthropod control agents
WO2017111152A1 (en) Oxadiazole compounds and use thereof
WO2017110862A1 (en) Oxadiazole compound and use thereof
WO2018117034A1 (en) Oxadiazole compound and plant disease control method
EP3483144B1 (en) Heterocyclic compound and harmful arthropod controlling agent containing same
WO2017110861A1 (en) Plant disease control agent containing oxadiazole compound
JP6914322B2 (en) Its use as an oxadiazole compound and pesticide
WO2017169893A1 (en) Oxadiazole compound and use thereof
JP7253498B2 (en) Heterocyclic compound and harmful arthropod control agent containing the same
JP7370432B2 (en) Heterocyclic compounds and compositions containing them
JP2019151553A (en) Oxadiazole compound and use thereof
WO2017073733A1 (en) Pest control composition and use thereof
WO2021153786A1 (en) Phenylacetic acid derivative, use therefor, and production intermediate thereof
JP2019089711A (en) Oxadiazole compound and application thereof
WO2019003956A1 (en) Oxadiazole compound and use thereof
JPWO2019083008A1 (en) Pyridine compound and pest control composition containing it