JPH03215476A - 6-aryl-2,4(1h,3h)-pyrimidinedione derivative and herbicide - Google Patents
6-aryl-2,4(1h,3h)-pyrimidinedione derivative and herbicideInfo
- Publication number
- JPH03215476A JPH03215476A JP2008827A JP882790A JPH03215476A JP H03215476 A JPH03215476 A JP H03215476A JP 2008827 A JP2008827 A JP 2008827A JP 882790 A JP882790 A JP 882790A JP H03215476 A JPH03215476 A JP H03215476A
- Authority
- JP
- Japan
- Prior art keywords
- cll
- cii
- sch
- cil
- scii
- 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
Links
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- 229910052757 nitrogen Inorganic materials 0.000 description 1
- GQPLMRYTRLFLPF-UHFFFAOYSA-N nitrous oxide Chemical group [O-][N+]#N GQPLMRYTRLFLPF-UHFFFAOYSA-N 0.000 description 1
- AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000005648 plant growth regulator Substances 0.000 description 1
- 238000012746 preparative thin layer chromatography Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 150000008512 pyrimidinediones Chemical class 0.000 description 1
- 235000009736 ragweed Nutrition 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- KKCBUQHMOMHUOY-UHFFFAOYSA-N sodium oxide Chemical compound [O-2].[Na+].[Na+] KKCBUQHMOMHUOY-UHFFFAOYSA-N 0.000 description 1
- 229910001948 sodium oxide Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000009331 sowing Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 229940035893 uracil Drugs 0.000 description 1
- 230000002747 voluntary effect Effects 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Landscapes
- Plural Heterocyclic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
Description
【発明の詳細な説明】
〔産業上の利用分野]
本発明は新規な6−アリールー2.4(IH,3+1)
−ビリミジンジオン誘導体を有効成分として含有する
選択性除草剤に関するものである。[Detailed description of the invention] [Industrial application field] The present invention provides a novel 6-aryleum 2.4 (IH, 3+1)
- A selective herbicide containing a pyrimidinedione derivative as an active ingredient.
従来から、重要作物、例えば、イネ、大豆、落花生、ヒ
マワリ、ソルゴー、小麦、トウモロコシ、ワタ、ビート
等を雑草から守り、これら重要作物の生産性を高めるた
めに多くの除草剤が実用化されてきた。特に近年、世界
的な人口増加に伴い、重要作物の生産性が世界の食糧経
済に直接影響を与えることは必至である.このことから
、農業従事者にとって、重要作物栽培時に障害となる雑
草を効率よく枯殺できる除草剤の開発が増々必要となっ
ている。このような除草剤として以下のような条件を備
えた薬剤の開発が切望されている。Traditionally, many herbicides have been put into practical use to protect important crops such as rice, soybeans, peanuts, sunflowers, sorghum, wheat, corn, cotton, and beets from weeds and to increase the productivity of these important crops. Ta. Particularly in recent years, with the global population increase, it is inevitable that the productivity of important crops will have a direct impact on the world food economy. For this reason, there is an increasing need for farmers to develop herbicides that can efficiently kill weeds that pose obstacles to the cultivation of important crops. There is a strong desire to develop such herbicides that meet the following requirements.
適度な残効性を有するもの(近年、土壌残留性の長い薬
物が後作・\被害を与えることが問題となっており、散
布後、適度な残効性を示すことが重要である。)、散布
後、速やかに雑草を枯殺するもの(特に作物生育初期段
階で、同時に発生してくる雑草を速やかに防除すること
は、その後の作物の生育条件を良くする。)、薬剤処理
回数が少いもの(このことは雑草防除作業の省略化を計
る上でも重要である。)、作物と雑草が混在するような
耕地に於いて両者茎葉部・\の同時処理により雑草だけ
を選択的に枯殺させるもの(不耕起栽培が普及するにと
もない、従来の土壌混和処理から生育期の茎葉処理が増
えている。)、作物収量に影響を与えないもの(作物収
穫時に、収量に影響を与える因子、例えば、生育抑制な
どを起こさないことが重要である.)が望ましい。Items with an appropriate residual effect (In recent years, it has become a problem that drugs that persist in the soil for a long time cause damage to subsequent crops, so it is important that they exhibit an appropriate residual effect after being sprayed.) , those that quickly kill weeds after spraying (especially in the early stages of crop growth, rapid control of weeds that emerge at the same time improves the growing conditions for subsequent crops), In cultivated land where crops and weeds coexist, it is possible to selectively control only weeds by simultaneously treating the stems and leaves of both plants. (With the spread of no-till cultivation, the use of foliage treatment during the growing season is increasing from the conventional soil mixing treatment.), and those that do not affect crop yield (when harvesting crops, For example, it is important not to cause growth inhibition, etc.).
しかしながら、既存の除草剤は必ずしも条件を全て満た
しているものではない。However, existing herbicides do not necessarily meet all the conditions.
一方、ウラシル誘導体の特定の化合物が除草活性を示す
ことは知られており、例えば、ThePesticid
e Manual 第8版、89頁The Brit
ishCrop Protection Counci
l ( 1 9 8 7年)等にウラシル骨格を持つ
除草剤の一つとしてブロマシル(Bromacil)が
記載されているが、施用薬量が!.6〜15kg/ha
と高い為、環境汚染などの点から好ましくなく、一部、
土壌残留の懸念もあり、除草剤として優れた化合物とは
言い難い。On the other hand, it is known that certain compounds of uracil derivatives exhibit herbicidal activity; for example, ThePesticide
e Manual 8th edition, page 89 The Brit
ishCrop Protection Council
Bromacil is described as one of the herbicides with a uracil skeleton in 1987, etc., but the amount of application is too low! .. 6-15kg/ha
Because it is expensive, it is not desirable from the viewpoint of environmental pollution,
It is difficult to say that it is an excellent compound as a herbicide, as there are concerns that it may remain in the soil.
本発明者らは、このような状況に鑑み、重要作物に対し
て選択性を示し、多くの雑草に対して低薬量で優れた除
草効果を有し、土壌処理、茎葉処理効果を兼ね備えた除
草剤を開発する為に研究を続けた結果、式(1)
〔式中、R+ , Rz , Ri , R4, Rs
は、それぞれ独立して水素原子、C,〜4アルキル、C
l〜4ハロアルキル、ハロゲン原子、シアノ、二トロ、
CI〜47ル?キシ、01〜4ハロアルコキシ、C.〜
4アルキルカルボニルまたはC,〜4アルコキシ力ルポ
ニルを示し、R6は水素原子、C1〜4アルキルまたは
C1〜,ハロアルキルを示し、
R7は水素原子、Cl〜4アルキル、ハロゲン原子また
は二トロを示し、
R[lは水素原子またはハロゲン原子を示し、R,はハ
ロゲン原子または二トロを示し、R1。は水素原子、ハ
ロゲン原子、シアノ、ニトロ、NRzR+■ (Rz
,R+zはそれぞれ独立して水素原子、自〜4アルキル
、C,〜4アルキルカルボニル、Cl〜4アル」キシ力
ルボニルまたはC.〜4アルキルスルホニルを示す。)
、
CO■RI:I (R+zは水素原子、ナトリウl、、
C,〜4アルキル、03〜,シクロアルキル、02〜,
アルケニル、03〜,アルキニル、フエニルまたはヘン
ジルを示す。)、OR+4 ,SRI4 (Rl4は
水素原子、01〜4アルキル、03〜6シク【7アルー
トル、02〜,アルケニルまたは03〜,アルキニルを
示す。)または
自〜4アルートルを示し、Rl6は水素原子、ナl・リ
ウム、c,〜,アル;トル、c:l〜,シクロアルキル
、02〜,アルケニル、C,〜5アルキニル、フェニル
またはベンジルを示す。)を示し、
Xは酸素原子または硫黄原子を示す。〕で表されるウラ
シル誘導体と、R9とR1。が環を形成する場合式(n
)、(III)
〔式中、R. , R2, R:l, R. , 1?
s ,れ 、R7,R.,Xは前記と同様の意味を表し
、
Rl7は水素原子、C,〜4アハバVル、C2〜,アル
ゲニル、03〜,アノレキニノレ、べ冫′ジノレ、C1
〜4ハロアノレキノレ、を示す。〕で表されるウラシル
誘導体(以下、本発明化合物と称する。)が、土壌処理
、草葉処理のいずれの処理方法に於いても、イヌホウズ
キ、チョウセンアサガオ、イチビ、アメリカキンゴジカ
、マルバアサガオ、イヌビュ、アオビュ、オナモミ、ブ
タクサ、ハキダメギク、セイヨウトゲアザミ、ノボロギ
ク、イヌガラシ、ノハラガラシ、ナズナ、イヌタデ、ス
ヘリヒュ、シロザ、コアカザ、ハコベ、オオイヌノフグ
リ、ツユクサ、ホトケノザ、ヒメオトリコソウ、ヤエム
グラ、スミレ、アメリカツノクサネム、エビスグサ等の
広葉雑草、イヌビエ、メヒシバ、カラスムギ、エノコロ
グサ、スズメノテッポウ等のイネ科雑草、ハマスゲ等の
カヤツリグサ科雑草、ウリカワ、クマガヤツリ、ミズガ
ヤツリ、ホタルイ、コナギ、キカシグサ、タイヌビエ等
の各種水田雑草に高い殺草力を有する。また重要作物で
ある小麦、トウモロコシ、大麦、大豆、イネ、棉、ピー
ナッツ、ビート、ソルガム等に安全に使用できる。In view of these circumstances, the present inventors developed a compound that exhibits selectivity for important crops, has excellent herbicidal effects against many weeds at low doses, and has both soil treatment and foliage treatment effects. As a result of continuing research to develop herbicides, the formula (1) [where R+, Rz, Ri, R4, Rs
are each independently a hydrogen atom, C, ~4 alkyl, C
l~4 haloalkyl, halogen atom, cyano, nitro,
CI ~ 47 le? xy, 01-4 haloalkoxy, C. ~
4 alkylcarbonyl or C,~4 alkoxy group, R6 represents a hydrogen atom, C1~4 alkyl or C1~, haloalkyl, R7 represents a hydrogen atom, Cl~4 alkyl, a halogen atom, or nitro, R [l represents a hydrogen atom or a halogen atom, R represents a halogen atom or a nitrous atom, R1. is hydrogen atom, halogen atom, cyano, nitro, NRzR+■ (Rz
, R+z each independently represents a hydrogen atom, ˜4 alkyl, C, ˜4 alkylcarbonyl, Cl˜4 alkyl carbonyl, or C. ~4 alkylsulfonyl. )
, CO■RI:I (R+z is a hydrogen atom, sodium l,
C, ~4 alkyl, 03~, cycloalkyl, 02~,
Indicates alkenyl, 03~, alkynyl, phenyl or henzyl. ), OR+4, SRI4 (Rl4 represents a hydrogen atom, 01-4 alkyl, 03-6 cyclo[7-alutol, 02-, alkenyl or 03-, alkynyl]) or self-4 allutol, Rl6 is a hydrogen atom, represents sodium, c, ~, al; tolu, c:l ~, cycloalkyl, 02~, alkenyl, C, ~5 alkynyl, phenyl or benzyl. ), and X represents an oxygen atom or a sulfur atom. ], R9 and R1. When forms a ring, the formula (n
), (III) [wherein R. , R2, R:l, R. , 1?
s,re,R7,R. ,
〜4 haloanorequinole. ] The uracil derivative represented by (hereinafter referred to as the compound of the present invention) can be used in both soil treatment and grass foliage treatment to treat the effects of the uracil derivatives, such as Japanese brilliance, Datura vulgare, Japanese trumpet, American golden deer, Malva morning glory, Inuvium, Broad-leaved plants such as Japanese aobu, Japanese thornweed, ragweed, Japanese trifoliate, Japanese staghorn thistle, American violet, Japanese dogwood, Japanese field mustard, shepherd's purse, Japanese knotweed, Japanese knotweed, Japanese whiteweed, Japanese chickweed, chickweed, Japanese blackwort, dayflower, hotokenoza, stagweed, common violet, violet, American hornwort, blackberry, etc. It has a high herbicidal power against various rice field weeds such as weeds, grass weeds such as Japanese grasshopper, Japanese grasshopper, oat, hackberry grass, and Japanese grasshopper, Cyperaceae weeds such as Cyperus spp. It can also be safely used on important crops such as wheat, corn, barley, soybeans, rice, cotton, peanuts, beets, and sorghum.
本発明化合物は従来の除草剤に比べて、低薬量で速効的
に高い除草効果を有し、多種の雑草に対して土壌処理、
茎葉処理のいずれの方法に於いても適用出来ることが特
徴である。Compared to conventional herbicides, the compound of the present invention has a high herbicidal effect at a low dosage and is fast-acting, and can be used for soil treatment and treatment against a wide variety of weeds.
The feature is that it can be applied to any method of foliage treatment.
本発明化合物は新規なウラシル誘導体である。The compound of the present invention is a novel uracil derivative.
その合成法としては、例えばコンブレヘンシブ・ヘテロ
サイクリック・ケミストリー第3巻、57頁、1984
年(A.R.κaLritzky , et al,,
Comprehensive Heterocycli
c ChemisLry , volume3.57
(1984))等に記載されている合成法などを参考に
してウラシル骨核を合成することが出来る。また出発原
料となるアルキルアロイルアセテート誘導体はケミカル
・アンド・ファーマセティカル・プルテン第32巻、4
97頁、1984年(T.Sano, et al.,
Chew. Pharm.Bull., 32 (2
)+?97,(1984))等を参考に合成出来る。As for its synthesis method, for example, Combrehensive Heterocyclic Chemistry Vol. 3, p. 57, 1984
Year (AR.κa Lritzky, et al,,
Comprehensive Heterocycle
c ChemisLry, volume3.57
(1984)) etc., the uracil bone core can be synthesized. In addition, the alkylaroyl acetate derivatives used as starting materials are described in Chemical and Pharmaceutical Pluten Vol. 32, 4.
97 pages, 1984 (T. Sano, et al.,
Chew. Pharm. Bull. , 32 (2
)+? 97, (1984)).
上述の方法も含めて、スキーム(1)〜(5)に示した
合成ルートで本発明化合物を得ることが出来る(スキー
ム(1)のR l”” R r。、Xは前述と同じ意味
を表わす。R2。は例えば、低級アルキル、ペンジルフ
エニル、CH,Co■■などを表わし、acidは例え
ばパラトルエンスルホン酸、濃硫酸、などを表わしba
seは例えば、水素化ナトリウム、ソジウムメ1〜キサ
イド、炭酸カリウムなどを表わす。The compounds of the present invention can be obtained by the synthetic routes shown in schemes (1) to (5), including the above-mentioned methods (R l"" R r in scheme (1), and X have the same meanings as above). R2 represents, for example, lower alkyl, pendylphenyl, CH, Co■■, acid represents, for example, para-toluenesulfonic acid, concentrated sulfuric acid, etc.
se represents, for example, sodium hydride, sodium oxide, potassium carbonate, or the like.
スキーム(2)のR1〜R1。、Xは前述と同し意味を
表わす。Il,。、R21 はそれぞれ独立して、例え
ば低級アル;トル、ベンジル、フエニル、CH2C02
11 ナどを表わし、baseは例えば、水素化ナトリ
ウム、ソジウムメトキサイト、炭酸カリウムなどを表わ
す。R1 to R1 in scheme (2). , X have the same meanings as above. Il,. , R21 are each independently, for example, lower alk; tolu, benzyl, phenyl, CH2C02
11 represents sodium, and base represents, for example, sodium hydride, sodium methoxite, potassium carbonate, etc.
スキーム(3)のR,−R,。、Xは前述と同し意味を
表わす。R2(l + 112,はそれぞれ独立し′ζ
、例えば低級アルキル、ベンジル、フェニル、CH2C
Oall ナどを表わし、acidは、例えば酢酸、ト
リフルオロ酢酸などを表わし、baseは、例えば水素
化ナ1・リウム、ソジウムメトキサイド、炭酸カリウl
、などを表わす。R, -R, in scheme (3). , X have the same meanings as above. R2(l + 112, are each independent ′ζ
, such as lower alkyl, benzyl, phenyl, CH2C
Oall represents sodium, acid represents, for example, acetic acid, trifluoroacetic acid, etc., and base represents, for example, sodium hydride, sodium methoxide, potassium carbonate.
, etc.
スキーム(4)のR+””’R+o , Xは前述と同
じ意味を表わす。acidは例えば酢酸、トリフルオロ
酢酸などを表わし、baseは、例えば水素化ナトリウ
ム、ソジウムメトキサイド、炭酸カリウム、ピリジンな
どを表わす。In scheme (4), R+""'R+o and X represent the same meaning as described above. Acid represents, for example, acetic acid, trifluoroacetic acid, etc., and base represents, for example, sodium hydride, sodium methoxide, potassium carbonate, pyridine, etc.
スキーム(5)のR,〜Rho 、Xは前述と同じ意味
を表わす。ハロゲン化剤としては、例えば、弗素、塩素
、臭素、沃素、スルフリルクロライドなどを表わし、二
トロ化剤としては、例えば硝酸、硝酸銅、硝酸イソアミ
ルなどを表わす。)。R, ~Rho, and X in scheme (5) have the same meanings as above. Examples of the halogenating agent include fluorine, chlorine, bromine, iodine, and sulfuryl chloride, and examples of the nitration agent include nitric acid, copper nitrate, and isoamyl nitrate. ).
以下に本発明化合物及び中間体の合成例を参考例として
具体的に述べるが、本発明は、これらによって限定され
るものではない。Synthesis examples of the compounds and intermediates of the present invention will be specifically described below as reference examples, but the present invention is not limited thereto.
(以下、余白)
スキーム(+)
れ
±(但し、
X=0)
R6
Hal
(れ)zsO4
d
(但し、
X
0)
スキーム(2)
base
R6
}fat
(R,)2SO4
K2CO:+
NaH
スキーム(3)
d
base
H4
H5
1《6
X
ビ10
d
スキーム(4)
Rll
スキーム(5)
(以下、
余白)
盤劣劃二上
エチル 3
ペノエート
アミノ
3
フエニル−2
プロ
0
11
CHffCONI14
0
エチル ヘンゾイルアセテートl O. O g、酢酸
アンモニウム20.1g,エタノール52mlの混合物
に、lO’c以下で酢酸1 5. 8 gを滴下した。(Hereafter, blank space) Scheme (+) Re ± (However, X = 0) R6 Hal (Re)zsO4 d (However, X 0) Scheme (2) base R6 }fat (R,)2SO4 K2CO: + NaH Scheme ( 3) d base H4 H5 1《6 .. To a mixture of Og, 20.1 g of ammonium acetate, and 52 ml of ethanol, add 1.0 g of acetic acid at less than 10'c. 8 g was added dropwise.
室温に昇温後、加熱して還流下に4時間攪拌した。After raising the temperature to room temperature, the mixture was heated and stirred under reflux for 4 hours.
反応終了後、溶媒を除去し、ジエチルエーテルに溶解し
た。ついで希塩酸、水、飽和食塩水で洗浄および無水硫
酸ナ1・リウムでの乾燥、溶媒留人を行うことにより、
目的化合物8. 6 5 gを茶色オイルとして得た。After the reaction was completed, the solvent was removed and the residue was dissolved in diethyl ether. Then, by washing with dilute hydrochloric acid, water, and saturated saline, drying with anhydrous sodium sulfate, and removing the solvent,
Target compound 8. 65 g were obtained as a brown oil.
書』l性二』2
3−(4−1口ロー2−フルオロフエニル)6−フエニ
ルー2.4(IH,3+1)一ビリミジンジオンNaH
F
0
水素化ナトリウム(純度55%)0.60g、ジメチル
ホルムアミドlidの混合物にO゜cでエチル3−アミ
ノー3−フェニルー2−プロペノエート2. 6 3
gを加えた。室温に昇温20分後、エチル4−クロロ−
2−フルオロフエニルカーハメート3. 0 0. g
を加えて、約130゜Cに加熱した.2時間後、室温に
冷却し、減圧下ジメチルホルムアミドを除去した後、水
を加え、ジエチルエーテルで3回洗浄した。水層を濃塩
酸で酸性にした後、析出した結晶を濾過し、乾燥するこ
とにより、目的化合物2. 8 7 gを淡黄色結晶と
して得た。2 3-(4-1-2-fluorophenyl)6-phenyl-2.4(IH,3+1)-pyrimidinedione NaH F 0 Sodium hydride (purity 55%) 0.60 g 2. Ethyl 3-amino-3-phenyl-2-propenoate at 0°C in a mixture of dimethylformamide lid. 6 3
g was added. After heating to room temperature for 20 minutes, ethyl 4-chloro-
2-fluorophenyl carhamate 3. 0 0. g
was added and heated to approximately 130°C. After 2 hours, the mixture was cooled to room temperature, dimethylformamide was removed under reduced pressure, water was added, and the mixture was washed three times with diethyl ether. After making the aqueous layer acidic with concentrated hydrochloric acid, the precipitated crystals were filtered and dried to obtain the target compound 2. 87 g was obtained as pale yellow crystals.
薬亙涯二よ
3−(4−1口ロー2−フル才ロフェニル)1−メチル
−6〜フェニルー2.4(II+,3H)一ピリミジン
ジオン
U
Natl
(CL)zsO4
水素化ナトリウム(純度55%) 0. 0 7 g、
ジメチルホルムアミド5 mlの混合物に、3−(4ク
ロロー2−フルオロフエニル)−6−フエニル2.4(
111.31)一ピリミジンジオン0. 5 0 gを
加えた後、ジメチル硫酸0. 3 0 gを滴下し、2
時間攪拌した。減圧下ジメヂルホルムアミドを除去し、
水を加え酢酸エチルで抽出した。飽和食塩水での洗浄、
無水硫酸ナl− IJウムでの乾燥、酢酸エチル除去を
経て、粗生成物を得た。これを分取薄層クロマトグラフ
ィ−(展開溶媒ヘキサンー酢酸エチル2:l)で精製す
るごとにより、 目的化合物0. 4 2 gを白色結
晶として得た。3-(4-1) 1-methyl-6-phenyl-2.4(II+,3H)-pyrimidinedione U Natl (CL)zsO4 Sodium hydride (purity 55%) ) 0. 0 7 g,
3-(4chloro2-fluorophenyl)-6-phenyl 2.4(
111.31) Monopyrimidinedione 0. After adding 50 g, dimethyl sulfate 0. Drop 30 g,
Stir for hours. Remove dimedylformamide under reduced pressure;
Water was added and the mixture was extracted with ethyl acetate. Washing with saturated saline,
After drying over anhydrous sodium sulfate and removing ethyl acetate, a crude product was obtained. Each time this was purified by preparative thin layer chromatography (developing solvent: hexane-ethyl acetate 2:1), 0.0% of the target compound was obtained. 42 g were obtained as white crystals.
薬考貫二↓
3−(4−1ロロー2−フルオロフェニル)6−(2−
クロロフエニル) −2.4(ill,3+1)−ピリ
ミジンジオン
NaH
F
水素化ナトリウム(純度55%) 0. 2 9 g、
ジメチルホルムアミド6−の混合物に0゜Cでエチル3
−アミノー3−(2−クロロフェニル)−2プロベノエ
ート1. 5 0 gを加えた。10分後、30゜Cに
冷却し、4−クロロ−2−フルオロフェニルイソシアナ
ート1.16g,トルエン6 mlの溶液を滴下して加
えた。その後、徐々に室温に昇温し、さらに80゜Cに
1時間加熱した。反応終了後、溶媒を減圧下除去し、水
を加えてジエチルエーテルで3回洗浄した。水層を濃塩
酸で酸性にした後、析出した結晶を濾過し、乾燥するこ
とにより、目的化合物1. 2 0 gを淡黄色結晶と
して得た。Yakukon Kanji ↓ 3-(4-1 Roro 2-fluorophenyl) 6-(2-
chlorophenyl) -2.4(ill,3+1)-pyrimidinedione NaH F Sodium hydride (purity 55%) 0. 29 g,
Add ethyl 3 to a mixture of dimethylformamide 6 at 0°C.
-Amino-3-(2-chlorophenyl)-2probenoate 1. 50 g was added. After 10 minutes, the mixture was cooled to 30°C, and a solution of 1.16 g of 4-chloro-2-fluorophenyl isocyanate and 6 ml of toluene was added dropwise. Thereafter, the temperature was gradually raised to room temperature and further heated to 80°C for 1 hour. After the reaction was completed, the solvent was removed under reduced pressure, water was added, and the mixture was washed three times with diethyl ether. After making the aqueous layer acidic with concentrated hydrochloric acid, the precipitated crystals were filtered and dried to obtain the target compound 1. 20 g was obtained as pale yellow crystals.
会IL−足
:3−(4−1口ロー2−フルオロフヱニル)=6−(
2−クロロフェニル)一1−メチル2.4(IH,3}
1)一ピリミジンジオン0
CI131
κ2CO,
3−(4−1口ロー2−フルオロフェニル)6−(2−
クロロフヱニル)−2.4(l■.311)一ピリミジ
ンジオン0. 5 0 gを、ジメチルホルムアミド5
mllに溶解し、無水炭酸カリウム0. 2 4 g
、ヨウ化メチル0. 2 4 gを加え、4時間攪拌し
た。反応終了後、水に注入し、析出した結晶を濾過、乾
燥することにより、目的化合物0. 4 9 gを淡黄
色結晶として得た。Association IL-foot: 3-(4-1 mouth low 2-fluorophenyl) = 6-(
2-chlorophenyl)-1-methyl 2.4(IH,3}
1) pyrimidinedione 0 CI131 κ2CO, 3-(4-1-2-fluorophenyl)6-(2-
Chlorophenyl)-2.4(l■.311)-pyrimidinedione 0. 50 g of dimethylformamide
ml of anhydrous potassium carbonate. 2 4 g
, methyl iodide 0. 24 g was added and stirred for 4 hours. After the reaction is completed, the target compound is poured into water, and the precipitated crystals are filtered and dried to obtain 0.0% of the target compound. 49 g was obtained as pale yellow crystals.
次に前記参考例あるいはスキーム(1)〜(5)に準じ
て合成された化合物の番号と構造を第1表に、そ
れらの化合物の物理的性質を第2表に示す。Next, Table 1 shows the numbers and structures of the compounds synthesized according to the reference examples or schemes (1) to (5), and Table 2 shows the physical properties of these compounds.
(以下、余白)
第
1
表
第
1
表
(続き)
第
l
表(続き)
第
■
表(続き)
第
l
表
(続き)
第
1
表
(続き)
第
2
表
本発明
化合物
漱
’H−NMR
]溶媒l
δ(ρρ一)
物理的性質
6.05(111.s),7.19
11.57(IH,br s)
[d6−DMSOI
〜8.02(811,m),
mp=242〜243゜C
3.25(311,s),5.82(Itl,s).7
. 10〜7.76(8H,a+)
IcDc 1 3]
a+p=200.5〜203゜C
2.41(3H,s),5.58(IH,s),7.0
6 〜7.50(7H,m),11.43(IH,br
s)Idi−DMSOI m
p=191〜195゜C2.26(3H,s),3.0
4(3H,s).5.68(E,s).7.00 〜
7.62(7H,s)[CDC 1 zl
mp・204〜205℃
2.40(3H,s),6.05(IH,s),7.0
7〜?.75(78,si).11.60(1}1,b
r s)[di−DMSOI
mp=220〜223゜C2.40(3H,s),3.
20(38,s),5.71(IH,s),7.03
〜7.41(7Hv)[db−DMSOI
卯・149〜151.5゜C
第
2
表(続き)
本発明
化合物
患
II−NMR
(溶媒1
δ(ρps+)
物理的性質
2.37(311,s),5.94(IH,s),6.
97〜7.80(7H,m),11.23(IH,br
s)[da−DMSOI
s+p−141〜145°C2.39(3H.s),3
.19(311,s),5.70(IH,s),7.3
5(7H,br s)[d6−DMSOI
mp=156〜160゜C
6.15(IH,s).7.14
11.84(IH,br s)
[d,−DMSOI
〜8.10(711,m).
s+p=233〜235゜C
3.20(3H,s),5.85(IH,s),7.1
2〜7.40(3H,鋤),7.49 〜7.86(
4H4)[d6−DMSOI
sp=139〜!42゜C
6.09(IH,s),7.12 〜7.60(411
,m),7.76(2H,br d,J=10Hz),
7.96(2H.br d,J=lOHz)[di−D
MSOI
mp・295〜298℃
3.17(3■.s),5.73(LH,s),7.1
3〜7.46(311,m).7.66(2H,br
d,J=10Hz),7.84(2H,br d,J=
l011z)[di−DMSOI
sp・250〜253℃
第
2
表(続き)
本発明
化合物
階.
+I−NMR
[溶媒]
δ(ppm)
物理的性質
6.05(111.s),?.10
11.77(1}1,br s)
[d6−DMSOI
〜8.05(7+1,■),
mp=186〜190゜C
3.26(3H s).5.86(IH,s)7.02
〜7.96(7H,m)
[CDC 1 zl
mp= 199〜200゜C
6. 10(IH, s) , 7.0711.66(
IH,br s)
[d,−DMSOI
〜7.79(711,m)
mp・269〜271 ’C
3.25(3H,s),5.80(Ill,s),7.
Ol〜7.83(7H,m)
[CDC 1 3]
叩=180〜181 ″C
6.02(1}1,s).7.12 〜7.60(5
11,m),7.87(28,dd,J=6.10Hz
).11.69(IH,br s)Ida−DMSOI
mp=270〜273゜C
3.18(3H,s).5.79(ltl,s).7,
21〜7.88(7H4)
[d!−DMSOI
mp=273〜274 ℃
第
2
表(続き)
本発明
化合物
階
’H−NMR
1溶媒1
δ(ppm)
物理的性質
5.70(III,s).7.10
11.67(IH,br s)
[db−DMSOI
〜7.6N711j),
mp=235〜238゜C
3.15(311,s),5.74(IH,s),7.
04〜7.61(7tl,ai)
[coc1il
町ト212〜215゜C
6. 11 (Ill, s) , 7.2511.6
9(IH,br s)
[d,−DMSOI
〜7.96(711,m),
一p・248〜253 ゜C
3.21 (3H, s) , 5. 73(IH,
s) ,7.09〜?.61(7}1, m)
[CDC 1 zl
mp=128 〜131 ’C
6.01(18,s),7.04 〜7.53(311
,si),7. 41(211, d, J=lOHz
) , 7. 73 (2H, d, J=10Hz)
, 11. 73 (III,br s) [
da−DMSOI mp=160 〜1
62゜C3.31(3H,s),5.83(IH,s)
,7.30〜7.68(3H,m),7.69(4H[
di−DMSOI
S)
lIlp・300゜C以上
次に、本発明に含まれる化合物の例を、前記化合物1〜
24も含めて、それぞれ第3表、第4表、第5表に示す
が、本発明は、これらによって限定されるものではない
。(Hereinafter, blank spaces) Table 1 Table 1 (Continued) Table I (Continued) Table ■ (Continued) Table I (Continued) Table 1 (Continued) Table 2 H-NMR of compounds of the present invention] Solvent l δ (ρρ -) Physical properties 6.05 (111.s), 7.19 11.57 (IH, br s) [d6-DMSOI ~8.02 (811, m), mp = 242 ~ 243 °C 3.25 (311, s), 5.82 (Itl, s). 7
.. 10-7.76 (8H, a+) IcDc 1 3] a+p=200.5-203°C 2.41 (3H, s), 5.58 (IH, s), 7.0
6 ~ 7.50 (7H, m), 11.43 (IH, br
s) Idi-DMSOI m
p=191~195°C2.26 (3H, s), 3.0
4 (3H, s). 5.68(E,s). 7.00 ~
7.62 (7H, s) [CDC 1 zl mp・204-205°C 2.40 (3H, s), 6.05 (IH, s), 7.0
7~? .. 75 (78, si). 11.60(1}1,b
r s) [di-DMSOI
mp=220-223°C2.40 (3H, s), 3.
20 (38, s), 5.71 (IH, s), 7.03
~7.41 (7Hv) [db-DMSOI
Rabbit・149-151.5°C Table 2 (continued) Compound II-NMR of the present invention (solvent 1 δ(ρps+) Physical properties 2.37 (311, s), 5.94 (IH, s), 6.
97-7.80 (7H, m), 11.23 (IH, br
s) [da-DMSOI
s+p-141~145°C2.39 (3H.s), 3
.. 19 (311, s), 5.70 (IH, s), 7.3
5 (7H, br s) [d6-DMSOI mp=156-160°C 6.15 (IH, s). 7.14 11.84 (IH, br s) [d, -DMSOI ~8.10 (711, m). s+p=233~235°C 3.20 (3H, s), 5.85 (IH, s), 7.1
2-7.40 (3H, plow), 7.49-7.86 (
4H4) [d6-DMSOI
sp=139~! 42°C 6.09 (IH, s), 7.12 ~ 7.60 (411
, m), 7.76 (2H, br d, J=10Hz),
7.96 (2H.br d, J=lOHz) [di-D
MSOI
mp・295~298℃ 3.17 (3■.s), 5.73 (LH, s), 7.1
3-7.46 (311, m). 7.66 (2H, br
d, J=10Hz), 7.84(2H,br d,J=
l011z) [di-DMSOI
sp・250-253°C Table 2 (Continued) Compounds of the present invention. +I-NMR [Solvent] δ (ppm) Physical properties 6.05 (111.s), ? .. 10 11.77 (1}1, br s) [d6-DMSOI ~8.05 (7+1, ■), mp=186~190°C 3.26 (3H s). 5.86 (IH, s) 7.02
~7.96 (7H, m) [CDC 1 zl mp= 199~200°C 6. 10(IH, s), 7.0711.66(
IH, br s) [d, -DMSOI ~7.79 (711, m) mp 269 ~ 271 'C 3.25 (3H, s), 5.80 (Ill, s), 7.
Ol ~ 7.83 (7H, m) [CDC 1 3] Hit = 180 ~ 181''C 6.02 (1} 1, s). 7.12 ~ 7.60 (5
11, m), 7.87 (28, dd, J = 6.10Hz
). 11.69 (IH, br s) Ida-DMSOI
mp=270-273°C 3.18 (3H, s). 5.79(ltl,s). 7,
21~7.88 (7H4) [d! -DMSOI mp=273-274°C Table 2 (Continued) Compounds of the Invention H-NMR 1 Solvent 1 δ (ppm) Physical Properties 5.70 (III, s). 7.10 11.67 (IH, br s) [db-DMSOI ~7.6N711j), mp=235~238°C 3.15 (311, s), 5.74 (IH, s), 7.
04~7.61 (7tl, ai) [coc1il town 212~215°C 6. 11 (Ill, s), 7.2511.6
9 (IH, br s) [d, -DMSOI ~7.96 (711, m), 1p・248 ~ 253 °C 3.21 (3H, s), 5. 73 (IH,
s) ,7.09~? .. 61 (7} 1, m) [CDC 1 zl mp=128 ~ 131 'C 6.01 (18, s), 7.04 ~ 7.53 (311
, si), 7. 41 (211, d, J=lOHz
), 7. 73 (2H, d, J=10Hz)
, 11. 73 (III, br s) [
da-DMSOI mp=160 ~1
62°C3.31 (3H, s), 5.83 (IH, s)
, 7.30-7.68 (3H, m), 7.69 (4H[
di-DMSOIS) lIlp・300°C or higher Next, examples of the compounds included in the present invention will be described below.
24 are shown in Tables 3, 4, and 5, respectively, but the present invention is not limited thereto.
(以下、余白) 第3 1表 R1。(Hereafter, margin) Third 1 table R1.
R.
11
CH,
CH3
C11,
C113
CI1.
CH3
CI3
CL
CB.
RIG
?1
11
CO■lI
CO■11
CO■C]13
CO■CI+3
CO■C 2I+ 5
COzCzHs
CO■CH(CHz)z
CO■CH(CH3)2
h0
R.
CH3
C11,
CH.
CH.
CH.
CH3
CH,
C113
C113
CH.
Cl3
CH.
CH3
CH.
CH.
C!13
Clh
CH3
RIG
?O■
Nil■
Nl1■
N(CH3)2
N(C2115)2
NllCOCH3
NHCOCH,
NHCO2CH3
NIICO2CH3
NHSOzCHz
NIISO■CH.
NHSO■C2H,
NHSOzCztls
CO■H
CO211
cozct+:+
CO■CH.
CO.C.H,
?IG
CO2C.ll,
CO■Cl(CHs)z
COzCII(Cll+)z
?O■CHzCH=CHz
CO2ClhCH=CII■
CO■CH,C=CH
CO■CH2CミCH
CO■C.H.
COzCbHs
CO■CH2Cdb
COgCHzCills
OH
OH
OCH 2
CH,
CH3
CH2
CH3
Rl(1
OCR,
OC2BS
OC211S
OCII (CI13) z
OCR(CHff)z
OCHzCll=CHt
OCH.C旧CH2
0CH2CミCH
OCH2C=iCll
OCII(Cll3)C=CH
S}l
Sl1
SCH,
SCH2
SC.l+,
SCJs
SCH (Cll 3) 2
3CH(CH:+)z
CI.
CI.
CIl3
CH3
CH.
Cll3
CH3
Cl3
CH3
C113
CHi
Cllj
C■,
?CHzCH=CHz
SCII■CiCH
SCHzc:cH
SCH (CH3) C−CH
SCH (Cllz) CiCII
OCH.CO■■
OCII■CO■H
OC11■CO■C11,
OClhCOzGHz
OCHzCOtCJs
OCHzCO■C.H,
OCIIzCOzCH(CII+) tOCIbCOz
CH(CHz)z
?CH.CO■CHzCH=CHt
OCHzC(hcHzcH=cHz
OCHtCOzCHzC三C}I
OCH2Co■CH.CECII
OCH,Co■C6HS
OCHzCOzCaHs
OCH2CO■CHzCblls
OC]1■CO2CIl■C.H,
OCII (CH.)CO2B
QC}I (CHff) CO2}1
0CH(C}Is)C(hclIi
OCFI(Cuff)CO■CH3
0CR(CH.)CO■C t tl ,OCH (C
H s)CO■CzHs
CL
C11,
CI,
Cll.
C113
C113
CH3
CM,
CH3
?lf1
OCH(CI+3)CO■Cll (Clls) zO
CII(CH3)CO■CH(CHI)2?CR (C
H3)CO■CH.CH.CII■OCI(CII+)
COzCHzCトCIl■OCH(CHs)CO2Ct
l■CミCHOCH(CL)C(hctbc=cH
OCII(C}Ii)C(hCJs
OCH(CH3)COzC.HS
OCR(CHz)Co■ClbCJs
?,
C11,
C113
Cll:l
C11,
C{1,
CH.
CF.II
CF211
CF.CIl■
CFJCH.
C!1,
CI13
?IO
SCH2CO211
SCH2CO,H
SCH.CO■Cll:I
SCll.CO■CH.
scuzco■C.H,
scozco■t,US
■
OCR(CHi)z
■
CO■C11,
SCH.CO■CH(CHs)z
SCH2Co■CH(CHs)z
R.
CH.
C113
C11,
C113
Ctlx
CH.
CH.
CH.
CH3
Clh
Clh
CH3
CI.
CH3
CH,I
CI.
?1。R. 11 CH, CH3 C11, C113 CI1. CH3 CI3 CL CB. RIG? 1 11 CO■lI CO■11 CO■C] 13 CO■CI+3 CO■C 2I+ 5 COzCzHs CO■CH (CHz)z CO■CH (CH3)2 h0 R. CH3 C11, CH. CH. CH. CH3 CH, C113 C113 CH. Cl3 CH. CH3 CH. CH. C! 13 Clh CH3 RIG? O■ Nil■ Nl1■ N(CH3)2 N(C2115)2 NllCOCH3 NHCOCH, NHCO2CH3 NIICO2CH3 NHSOzCHz NIISO■CH. NHSO■C2H, NHSOzCztls CO■H CO211 cozct+:+ CO■CH. C.O. C. H,? IG CO2C. ll, CO■Cl(CHs)z COzCII(Cll+)z? O■CHzCH=CHz CO2ClhCH=CII■ CO■CH,C=CH CO■CH2CmiCH CO■C. H. COzCbHs CO■CH2Cdb COgCHzCills OH OH OCH 2 CH, CH3 CH2 CH3 Rl(1 OCR, OC2BS OC211S OCII (CI13) z OCR(CHff)z OCHzCl l=CHt OCH.C Old CH2 0CH2C MiCH OCH2C=iCll OCII(Cll3)C =CH S}l Sl1 SCH, SCH2 SC.l+, SCJs SCH (Cll 3) 2 3CH (CH:+)z CI. CI. CIl3 CH3 CH. Cll3 CH3 Cl3 CH3 C113 CHi Cllj C■, ? CHzCH=CHz SCII ■CiCH SCHzc: cH SCH (CH3) C-CH SCH (Cllz) CiCII OCH.CO■■ OCII■CO■H OC11■CO■C11, OClhCOzGHz OCHzCOtCJs OCHzCO■C.H, OCIIzCOzCH (CII+) tOCIbCOz
CH(CHz)z? CH. CO■CHzCH=CHt OCHzC (hcHzcH=cHz OCHtCOzCHzC3C}I OCH2Co■CH.CECII OCH, Co■C6HS OCHzCOzCaHs OCH2CO■CHzCblls OC]1■CO2CIl■C.H, OCII (CH.)CO2B QC}I (CHff ) CO2}1 0CH(C}Is)C(hclIi OCFI(Cuff)CO■CH3 0CR(CH.)CO■C t tl , OCH (C
H s) CO■CzHs CL C11, CI, Cll. C113 C113 CH3 CM, CH3? lf1 OCH (CI+3)CO■Cll (Clls) zO
CII(CH3)CO■CH(CHI)2? CR (C
H3) CO■CH. CH. CII■OCI (CII+)
COzCHzCトCIl■OCH(CHs)CO2Ct
l■CmiCHOCH(CL)C(hctbc=cH OCII(C}Ii)C(hCJs OCH(CH3)COzC.HS OCR(CHz)Co■ClbCJs ?, C11, C113 Cll:l C11, C{1, CH. CF.II CF211 CF.CIl■ CFJCH. C!1, CI13 ?IO SCH2CO211 SCH2CO,H SCH.CO■Cll:I SCll.CO■CH. scuzco■C.H, scozco■t,US ■ OCR ( CHi)z ■ CO■C11, SCH.CO■CH(CHs)z SCH2Co■CH(CHs)z R. CH. C113 C11, C113 Ctlx CH. CH. CH. CH3 Clh Clh CH3 CI. CH3 CH,I C.I. .?1.
SCH2CO■Cll■CH=CIl.SCHtCO■
CH2C■=CHz
SCHzCOzCHzC=CI
SCH,CO■CIl2CミCI1
SCH2CO■C.H,
SCH.CO■C.H,
SCH■COzCHgCJs
SCH.CO■Cll!C&l+5
SCH(CH3)CO■H
SCH(CL)CO■■
SCH(Clh)C(hclh
SCH(CH3)CO■CH.
SCH(CI13)CO■CzHs
SCH(CH3)CO■C2H,
SCH(CHz)CO■CH(CH3)!SCH(CH
I)CO■CH(CHi)z?Ctl(Ctl+)CO
zCll■CH・CI.SC■(CHz)Co■CHz
Cfl=CHzSCH (CIl :t) CO■cn
zc=coSCH(CH3)CO■ct+zc=coS
CH (CHz)C(hc6tls
scll (Cll3)COzCi.HsSCH(CL
)CO■CH.C,H,
SCH(CHz)CO■CHtC.lI5H
lI
NHSO■CtH%
R.
Cth
CH3
CH.
CH.
CI,
C11,
CI,
C■,
CH3
CH.
CI.
CH,
CFh
CH.
CH3
C]1,
?IG
CO■C 2It S
CO■C.H,
OCII (CHI) z
OCR(Cll3h
OCH,CEiCH
OCIhC:CH
OCII(CH3)C=CH
OCH (CH 3) C=CH
SCH(CHs)z
SCH (CH 3) !
SGHzCECII
SCH2C二CH
SCH(CH3)CミCll
SCH (Clh)C=CH
OC}l2CO■CHs
OCH.CO■CHI
Clh
F
NO2
?CII■CO■Cl13
C1{3
F
?O■
SCHzC(hclI:+
11
F
NO。SCH2CO■Cll■CH=CIl. SCHtCO■
CH2C■=CHz SCHzCOzCHzC=CI SCH,CO■CIl2CmiCI1 SCH2CO■C. H, SCH. CO■C. H, SCH■COzCHgCJs SCH. CO■Cll! C&l+5 SCH(CH3)CO■H SCH(CL)CO■■ SCH(Clh)C(hclh SCH(CH3)CO■CH. SCH(CI13)CO■CzHs SCH(CH3)CO■C2H, SCH(CHz)CO ■CH(CH3)!SCH(CH
I) CO■CH(CHi)z? Ctl(Ctl+)CO
zCll■CH・CI. SC■(CHz)Co■CHz
Cfl=CHzSCH (CIl :t) CO■cn
zc=coSCH(CH3)CO■ct+zc=coS
CH (CHz)C(hc6tls scll (Cll3)COzCi.HsSCH(CL
)CO■CH. C, H, SCH(CHz)CO■CHtC. lI5H lI NHSO■CtH% R. Cth CH3 CH. CH. CI, C11, CI, C■, CH3 CH. C.I. CH, CFh CH. CH3C]1, ? IG CO■C 2It S CO■C. H, OCII (CHI) z OCR(Cll3h OCH,CEiCH OCIhC:CH OCII(CH3)C=CH OCH (CH3) C=CH SCH(CHs)z SCH (CH3)! SGHzCECII SCH2C2CH S CH (CH3) CmiCll SCH (Clh)C=CH OC}l2CO■CHs OCH.CO■CHI Clh F NO2 ?CII■CO■Cl13 C1{3 F ?O■ SCHzC(hclI:+ 11 F NO.
■
{1
F
?O■
COzCH3
(以下、
余白)
0
S
0
O
第3−2表
?
■
NIIS(hczlls
NHSO■C21t,
CO■Cal1,
CO.C.l+,
OCH (Cll :l) t
OCH(CH3)z
OC82C:CI
OCR.C丑CH
OCI{(CFl3)CミCfl
OCI (CH+)C=CH
CH.
CH3
CI13
CH.
?CII (CI+3) z
Set−1 (Cflz) z
SCI12C三CH
SCII■C三CI+
SCH(CJ)C=CII
SCII (CI1 3’)CミC}lOCH2CO■
C11,
OCH2CO2CH3
?Cl12CO■CH3
?CH.CO■Cl,
?CI?(CH3)!
H
H
NHSOzCzlls
NHSO■C28S
co,c.t+,
CO■C,H,
OCH(CHz)z
OCR(CH3)z
oct+zc=co
OCHzC:(JI
OCR(CH3)CミCI
OCH (CH 2) C=CH
SCH(CHz)z
SCII(Clh)z
SCH.C=CH
SCHZC三CH
CH.
?CH(CH3)C三CH
SC}l(CL)CミCH
OCH2CO。CI.
OCH2CO■C11,
SCH2COZCH3
?CII■CO■C113
?1
0CH(CH3)z
CO■C]1,
N(SO■CHs)z
R,。■ {1 F? O ■ COzCH3 (hereinafter referred to as margin) 0 S 0 O Table 3-2? ■ NIIS(hczlls NHSO■C21t, CO■Cal1, CO.C.l+, OCH (Cll :l) t OCH(CH3)z OC82C:CI OCR.C丑CH OCI{(CFl3)CmiCfl OCI (CH+) C=CH CH. CH3 CI13 CH. ?CII (CI+3) z Set-1 (Cflz) z SCI12C3CH SCII■C3CI+ SCH(CJ)C=CII SCII (CI1 3')CmiC}lOCH2CO■
C11, OCH2CO2CH3? Cl12CO■CH3? CH. CO■Cl, ? CI? (CH3)! H H NHSOzCzlls NHSO■C28S co, c. t+, CO■C,H, OCH(CHz)z OCR(CH3)z oct+zc=co OCHzC: (JI OCR(CH3)CmiCI OCH (CH 2) C=CH SCH(CHz)z SCII(Clh)z SCH.C=CH SCHZC3CH CH. ?CH(CH3)C3CH SC}l(CL)CmiCH OCH2CO.CI. OCH2CO■C11, SCH2COZCH3 ?CII■CO■C113 ?1 0CH(CH3)z CO ■C]1, N(SO■CHs)z R,.
?CH3
0CH.CO■CH3
11
]I
NHS02C21+S
NHSO■C.ll,
CO2C2H,
cozczt+s
OCi{ (Clh) z
OCtl (C}IJ z
OCR2C=CI1
OCHxCミCI
OCR(Clh)C=CH
OCR(CH3)CECJI
SC■(CIl:l) t
SCH(CI:l)2
scHzc=co
C11,
CHff
C113
CH3
C113
?CH (CH :l) C=CH
SCH (CH 3)(jCH
OCHzCOzCth
OC{1■CO2CH:l
?CII■CO■CIl3
SCII■CO2CH3
CI I+
C l OCH (Cll J) 2CI C
ozC,Its
RIG
?1
■
NHSO2C2115
NIISOzCzHs
CO■C 2I+ ,
CO■C.l1,
OCII(CHi)z
OCII(CH3)!
0C82C三CH
ocHzc=cll
OCH (Cll,)C=CH
OCH(Cflz)CミCH
SCtl(CH:+)z
SCII(CH3)2
scozc=co
SCll2CミCI+
SCH (CH3)C,=CI
SCH (Cl z)C=CII
R6
Clh
C11,
R7
■
■
?s Rq R+。? CH3 0CH. CO■CH3 11]I NHS02C21+S NHSO■C. ll, CO2C2H, cozczt+s OCi{ (Clh) z OCtl (C}IJ z OCR2C=CI1 OCHxCmiCI OCR(Clh)C=CH OCR(CH3)CECJI SC■(CIl:l) t SCH(C I:l)2 scHzc=co C11, CHff C113 CH3 C113 ?CH (CH :l) C=CH SCH (CH 3) (jCH OCHzCOzCth OC{1■CO2CH:l ?CII■CO■CIl3 SCII■CO2CH3 CI I+ C l OCH (Cll J) 2CI C
ozC, Its RIG? 1 ■ NHSO2C2115 NIISOzCzHs CO■C 2I+ , CO■C. l1, OCII(CHi)z OCII(CH3)! 0C82C3CH ocHzc=cll OCH (Cll,)C=CH OCH(Cflz)CmiCH SCtl(CH:+)z SCII(CH3)2 scozc=co SCll2CmiCI+ SCH (CH3)C,=CI SCH (Cl z) C=CII R6 Clh C11, R7 ■ ■? s Rq R+.
1 0CII■CO,CIl3 Cl OCH2CO■CH, F F CH, C1{3 ■ ■ F F Cl Cl ?CHzCO■Cll3 SCII■COzCIh 第3 3表 R1。1 0CII■CO, CIl3 Cl OCH2CO■CH, F F CH, C1{3 ■ ■ F F Cl Cl ? CHzCO■Cll3 SCII■COzCIh Third 3 tables R1.
村,。village,.
? ■ NHSOzCzlls NHSO■C.H, CO■C2B, CO■CzHs OCH(CH3)z OCH(CI3)z ocozc=co OClhC:CH OCH(CH3)CミCl Clh ?IG SCH(CH1)z SCH(CHz)z SCII■C三CH SCII■C二Cll SCII (CH3)CミCH SCH (Cllz)C=CH OCII■COZCH:1 0C11■CO2CH:1 ?CII■CO■CH, SCH zcO zcII z 11 ■ F C2 H ■ ■ F Ce ■ I1 F F Cl 11 (以下、 余白) 0 S 0 第3 4表 R ?1 11 CO2H cotl CO2CH. CO。C113 COzCtHs CO2C2HS CO■CH (CIl:l) z CO2CII (CH3) z ?1。? ■ NHSOzCzlls NHSO■C. H, CO■C2B, CO■CzHs OCH(CH3)z OCH(CI3)z ocozc=co OClhC:CH OCH(CH3)CmiCl Clh ? I.G. SCH(CH1)z SCH(CHz)z SCII■C3CH SCII■C2Cll SCII (CH3) CmiCH SCH (Cllz)C=CH OCII COZCH: 1 0C11■CO2CH:1 ? CII CO CH, SCH zcO zcII z 11 ■ F C2 H ■ ■ F Ce ■ I1 F F Cl 11 (below, margin) 0 S 0 Third Table 4 R ? 1 11 CO2H cotl CO2CH. C.O. C113 COzCtHs CO2C2HS CO■CH (CIl:l) z CO2CII (CH3)z ? 1.
N(Cglls)z NHCOCH. NllCOCH3 NHCO■CH,l NHCOzCII+ NHSO■CH2 N}ISO!C}13 NHSO■C,H, NHSO■C . II , CO.H CO■H CO2Cl+3 CO■CH! CO2C2HS CO,C2HS CO2CH (CHI) t COzCH (Clli) z ?O■CllzCH=CHz CO■CHtCH−CHz CO■C}l.c−CH COgCHzC=CII CO■C.H, CO■C . II , C(hcHzcJIs CO■CHzCJs OH OH OCH 3 0CH, OC2HS QC2H, OCR(CH3)Z R,。N(Cglls)z NHCOCH. NllCOCH3 NHCO■CH,l NHCOzCII+ NHSO■CH2 N}ISO! C}13 NHSO■C,H, NHSO■C. II, C.O. H CO■H CO2Cl+3 CO■CH! CO2C2HS CO, C2HS CO2CH (CHI)t COzCH (Clli) z ? O■CllzCH=CHz CO■CHtCH-CHz CO■C}l. c-CH COgCHzC=CII CO■C. H, CO■C . II, C(hcHzcJIs CO■CHHzCJs OH OH OCH 3 0CH, OC2HS QC2H, OCR(CH3)Z R.
?CI12C}lエCll2
0CH2CH=CIl■
OCH2C:C}l
OCHzc=ct+
OC■(CH+)CミCH
OCR(CHz)C=:CH
Sl1
SH
SCtl3
SCzlls
SCJs
SCH (CI !) t
SCII (CH 3) z
SCHzCトCHz
SCHtCH=CHz
scuzc=co
SCII!C=CH
SCH (CH z)C=CH
(Jli
?CHzC(hll
OC11■CO■H
OC11■CO,CH3
0CHzco■Cth
OCHzC(hCzHs
OC!1■COzCJs
OC11■CO■CH(CIl:l)20CH.CO■
Cll(CH3)2
OCHzC(hcHzcH=clh
?CII■COzCHgCミCH
OCR2Co■CHzCミCI
OCR2C(hCJs
OCJCOzCJs
OCH2CO■ClhC6HS
OCHzC(hcHgcJs
OCII(Cth)COJ
OCII(CH3)CO!H
OCH(CH3)CO■CH3
0CH(CH:+)C(hclh
QC}l(CL)COzCg}Is
OCR(CHi)COzCztls
OCH(CHs)COtCH(CH*)zOCH(CH
s)COzCH(CH:+) zR1。? CI12C}l eCll2 0CH2CH=CIl■ OCH2C:C}l OCHzc=ct+ OC■ (CH+)CmiCH OCR(CHz)C=:CH Sl1 SH SCtl3 SCzlls SCJs SCH (CI!) t SC II (CH 3) z SCHzCtoCHz SCHtCH=CHz scuzc=co SCII! C=CH SCH (CH z)C=CH (Jli ?CHzC(hll OC11■CO■H OC11■CO,CH3 0CHzco■Cth OCHzC(hCzHs OC!1■COzCJs OC11■CO■CH(CIl:l)20 CH. CO■
Cll(CH3)2 OCHzC(hcHzcH=clh ?CII■COzCHgCmiCH OCR2Co■CHzCmiCI OCR2C(hCJs OCJCOzCJs OCH2CO■ClhC6HS OCHzC(hcHgcJs O CII(Cth)COJ OCII(CH3)CO!H OCH(CH3)CO■CH3 0CH(CH:+)C(hclh QC}l(CL)COzCg}Is OCR(CHi)COzCztls OCH(CHs)COtCH(CH*)zOCH(CH
s) COzCH (CH:+) zR1.
X
?CH (CH 3)CO■CH2Cll=CIl■O
CR(CH3)CO■CHZCI=CH20CH(CH
3)CO2CH2C三CIOCR (CH z)Co■
CH.C=CIOCII (CIl+)COzCiHs
OCII (CI+3) CO■C . I1 ,OC
H (Ctl a) CO■CHzCJ50CH(CH
3)CO■Cll■C 6H SSCH,CO■11
SCII■CO■H
SCH2COZCH3
SCII■CO■C113
SCH2CO■C 2 I+ !,
SGHzC(hCJs
CIll
CH3
CH3
C113
Cll:I
C]1,
C11,
CI.
CH3
?CII■CO■Cll (Cll 3) 2?CH,
CO■CH2CH=CHz
SCH.CO■Cl,CH=CIl■
scugco■CH2CミCll
SCHzCOz(JIzCミCH
SCH2CO■C.H,
SClhC(hCJs
SCII■CO2CH2C6H5
SCH2CO■CH2C6HS
SCH(CH3)CO2H
C113
C113
C113
?ID
SCII(Clli)COzCII3
SCH(Cth)CO■CH3
SCII (C}I :l) CO■C.H,SCH(
CH3)Co■C 2I+ ,SCH (CH:+)C
(hcIl (CI+3) zSCfl(CH3)CO
■CH(CH:+)z?l1(Cll3)Co■Cll
■C++=CHfSCI量(CH3)CO2Cll ■
C1トCll ■SCH(CHz)COzCHzCミC
HO
0
S
?IG
SCII (CI13)CO2C.IlsSCH (C
I! :l) CO■C.H,SCH (Cl 3)
CO■CH.C.l+,SCH (CH3)CO■CH
2C.HS■
11
NIISO■C . It ,
N II S O■C z If s
CO2C,11,
CO■CJs
OCII (C■3) 2
0CH(CH:l)Z
OCH.C三CH
ocHzc=clI
OCH (CI+3)C三CI
OCR(CH3)(jCH
SCH(CH3)2
C113
CH3
CI+3
CI+,
CI.3
CI1,
?,。X? CH (CH3)CO■CH2Cll=CIl■O
CR(CH3)CO■CHZCI=CH20CH(CH
3) CO2CH2C3CIOCR (CH z)Co■
CH. C=CIOCII (CIl+)COzCiHs
OCII (CI+3) CO■C. I1, O.C.
H (Ctl a) CO■CHzCJ50CH(CH
3) CO■Cll■C 6H SSCH,CO■11 SCII■CO■H SCH2COZCH3 SCII■CO■C113 SCH2CO■C 2 I+! , SGHzC (hCJs CIll CH3 CH3 C113 Cll:I C]1, C11, CI. CH3 ?CII■CO■Cll (Cll 3) 2?CH,
CO■CH2CH=CHz SCH. CO■Cl,CH=CIl■ scugco■CH2CmiCll SCHzCOz(JIzCmiCH SCH2CO■C.H, SClhC(hCJs SCII■CO2CH2C6H5 SCH2CO■CH2C6HS SCH(CH3)CO2H C1 13 C113 C113 ?ID SCII(Clli)COzCII3 SCH( Cth) CO■CH3 SCII (C}I :l) CO■C.H,SCH(
CH3)Co■C 2I+ ,SCH (CH:+)C
(hcIl (CI+3) zSCfl(CH3)CO
■CH(CH:+)z? l1(Cll3)Co■Cll
■C++=CHfSCI amount (CH3) CO2Cll ■
C1ToCll ■SCH(CHz)COzCHzCMiC
HO0S? IG SCII (CI13) CO2C. IlsSCH (C
I! :l) CO■C. H, SCH (Cl3)
CO■CH. C. l+, SCH (CH3)CO■CH
2C. HS■ 11 NIISO■C. It, N II S O■C z If s CO2C, 11, CO■CJs OCII (C■3) 2 0CH (CH:l)Z OCH. C3CH ocHzc=clI OCH (CI+3)C3CI OCR(CH3) (jCH SCH(CH3)2 C113 CH3 CI+3 CI+, CI.3 CI1, ?,.
SCH2C三C}I SC82C:CH SCH(CH:+)C=CH SCII (Ctl 3) CミCH OCH2CO■C113 0C11■C(hcHz SCH2C02CH3 ?CH2CO■C!13 H CO2CH3 RIG ?I ■ NIISO■C.lI, NHSO■C211, COzCzHs COzCzHs OCR(CHz)t OCH(Cl{3)z OCRzc=co OCHzcミCI OCH(CL)C=CII OCH(CI.)CミCH SCH(CH3)t SCH(CH3)2 SCHzc三Cl+ SCHzc二CH SCH(CH+)C=CH C11, C113 C113 Cll. ■ 11 ■ CF211 C}1, C]13 ?C11■CO■C113 OCH zco ZCI1 3 ?CH2CO■CH3 SCHzCOzCflz ?HSO■C . I1 , CO■CJs CO■C!H. OCH(CI+3)2 0CR (CIl:l) 2 0CHzC=CII OCR,C三CI OCR(CHi)C=CH OCII(CH:l)CミCFI SCH (Cllz) t SCH(CH3)2 5CII■CECI4 SCH2CミCFI SCH(Cth)CミCH SCfl <CH.J)C=CH OCHzCOzCHx C113 C113 SCH2CO2CFl3 ?CH■CO■C11, ?I CO,CIl3 0CII (Cll s) 2 11 ■ ■ NIISO■C z II s NIISO■Czlb ?OzCzlls OCI目(CH:+)z OCH (CH :l) 2 0C11■C三CH ocozcミCl+ OCR(CH3)CミCH OCR(CI.)CミCI SCII(CL)z SCH (Cl 3) ! SCII■CミCH SC■2C三CH SCII(CHz)CミCll SCII(CH3)CミCII OCII2CO2Cll3 0CH2CO■CH, C113 C]13 ?CII■C(hclh ?CH2CO■C11, ?{ II H NHSOzC211s NHSO。C2115 COzCJs CO■C z fl s OCII (CH:l) 2 0(Jl (Ctl+) 2 ocuzc=co OCR.CiCH OCH (Cll3)CミCH れ C11, C113 C113 C1{3 CH. C11, CI, CO, C11, C113 ?IG SCII (CH 3) 2 SCII(Cl!+) z SCH2C−CI+ SCH■C二Cl1 SCH(Cll3)CミCl{ SCII(CI+3)C三CH OCHzCOzCfl+ OCH.GO■CFI3 ?O■ ?CII■CO■CH3 SCl’hCOzCHi RIG (以下、 余白) 第3 5表 ? CO■H COzH CO■CH3 COzCtli COZC2HS CO■C 2H S CO■CH(CI+3)2 CO■Cll(CHi)z R6 R7 R8 R, R × ?(Czlls)z NHCOCI+3 NIICOCH3 NHCO■C113 NHCOzCIl+ NHSO■C]13 NHSO■CII3 NHSO■C.H, NHSO2CgHs CO.l+ CO2H CO■C!13 COzCth COzCzlls COzCJs CO■Cll(CH3)z COzCH(CHz)z RIG ?O2Cll■co=clIz CO■CH2CH=CH2 CO■CH.C:CH CO■Cll■C=CU CO2C.HS CO■C 6II S CO■CH2C61+5 CO■Cll■C b It s OH 011 0CH3 0CH 3 0C2HS OC2115 OCR (CI+ 3) 2 OCllzCH=CL OCHzCH=CIIz ocuzc=co OCR!CミCH O(Jl(Clh)CミCH OCII(Ctl+)C=CH SH SH SCH. R6 CH. CI. 0113 CH. Clh C113 C113 C11, C113 R1。SCH2C3C}I SC82C:CH SCH(CH:+)C=CH SCII (Ctl 3) C Mi CH OCH2CO■C113 0C11■C (hcHz SCH2C02CH3 ? CH2CO■C! 13 H CO2CH3 R.I.G. ? I ■ NIISO■C. lI, NHSO■C211, COzCzHs COzCzHs OCR(CHz)t OCH(Cl{3)z OCRzc=co OCHzc MiCI OCH(CL)C=CII OCH(CI.)CmiCH SCH(CH3)t SCH(CH3)2 SCHzc3Cl+ SCHzc2CH SCH(CH+)C=CH C11, C113 C113 Cll. ■ 11 ■ CF211 C}1, C] 13 ? C11■CO■C113 OCH zco ZCI1 3 ? CH2CO■CH3 SCHzCOzCflz ? HSO■C. I1, CO■CJs CO■C! H. OCH(CI+3)2 0CR (CIl:l) 2 0CHZC=CII OCR, C3CI OCR(CHi)C=CH OCII(CH:l)CmiCFI SCH (Cllz)t SCH(CH3)2 5CII■CECI4 SCH2C MiCFI SCH(Cth)CmiCH SCfl <CH. J) C=CH OCHzCOzCHx C113 C113 SCH2CO2CFl3 ? CH■CO■C11, ? I CO, CIl3 0CII (Clls) 2 11 ■ ■ NIISO ■ C z II s NIISO■Czlb ? OzCzlls OCI eyes (CH:+)z OCH (CH:l) 2 0C11■C3CH ocozcmi Cl+ OCR(CH3)CmiCH OCR(CI.)CmiCI SCII(CL)z SCH (Cl 3)! SCII■CmiCH SC■2C3CH SCII (CHz) Cll SCII(CH3)CmiCII OCII2CO2Cll3 0CH2CO■CH, C113 C] 13 ? CII■C (hclh ? CH2CO■C11, ? { II H NHSOzC211s N.H.S.O. C2115 COzCJs CO ■ C z fl s OCII (CH:l) 2 0 (Jl (Ctl+) 2 ocuzc=co OCR. CiCH OCH (Cll3)CmiCH Re C11, C113 C113 C1{3 CH. C11, CI, C.O. C11, C113 ? I.G. SCII (CH 3) 2 SCII (Cl!+)z SCH2C-CI+ SCH■C2Cl1 SCH(Cll3)CmiCl{ SCII (CI+3) C3CH OCHzCOzCfl+ OCH. GO■CFI3 ? O■ ? CII CO CH3 SCl’hCOzCHi R.I.G. (below, margin) Third Table 5 ? CO■H COzH CO■CH3 COzCtli COZC2HS CO■C 2H S CO■CH (CI+3)2 CO■Cll(CHi)z R6 R7 R8 R, R × ? (Czlls)z NHCOCI+3 NIICOCH3 NHCO■C113 NHCOzCIl+ NHSO C] 13 NHSO■CII3 NHSO■C. H, NHSO2CgHs C.O. l+ CO2H CO■C! 13 COzCth COzCzlls COzCJs CO■Cll(CH3)z COzCH(CHz)z R.I.G. ? O2Cll■co=clIz CO■CH2CH=CH2 CO■CH. C:CH CO■Cll■C=CU CO2C. H.S. CO■C 6II S CO■CH2C61+5 CO■Cll■C b It's OH 011 0CH3 0CH 3 0C2HS OC2115 OCR (CI+3) 2 OCllzCH=CL OCHzCH=CIIz ocuzc=co OCR! C Mi CH O(Jl(Clh)CmiCH OCII(Ctl+)C=CH S.H. S.H. SCH. R6 CH. C.I. 0113 CH. Clh C113 C113 C11, C113 R1.
SC2115
SC2}Is
SCH(CH3)2
SCH(Cfll)g
SCIIzCH=C}It
SCH2Cll=CH2
SClhCミCl1
SC82CECH
SCH(CH:+)C=CH
?l0
0C82Co■H
OCHzCOzH
OCHzCOzCHz
OCH,CO■C11,
OCII■COtCzHs
OCHzC(hCzHs
OCHzCOzCII (Cfl3) zOCH.GO
■CI (Cll 3) z?CH.CO■CHzCI
I=CHz
れ
CH,
Cl,
C113
Cl,
(Jl,
CH3
CIl3
CH,
C11,
CH,
C113
CH3
C113
CI+,
?.。SC2115 SC2}Is SCH(CH3)2 SCH(Cflll)g SCIIzCH=C}It SCH2Cll=CH2 SClhCmiCl1 SC82CECH SCH(CH:+)C=CH ? l0 0C82Co■H OCHzCOzH OCHzCOzCHz OCH,CO■C11, OCII■COtCzHs OCHzC(hCzHs OCHzCOzCII (Cfl3) zOCH.GO
■CI (Cll 3) z? CH. CO■CHHzCI
I=CHz CH, Cl, C113 Cl, (Jl, CH3 Cl13 CH, C11, CH, C113 CH3 C113 CI+, ?.
OCHzCOzCllzCミCI+
OCH.CO■Cll■CミCH
OCH2CO2C6+15
0CH2CO2C6115
oct+.co■CHzCbH5
0CH2CO■CH2C1,H5
0CII (Ctl z)CO■■
OCII (Cl 3)CO■H
OC11(CI+3)COZCI1:10CH(CIl
:l)CO■CH,
QC}l (CI13)CO■C . I+ ,OC1
1(C}13)CO,C2+15OCH(CH,)CO
2(Jl(CI13)20CH(CH:l)CO■Cl
l(CH3)2C113
C11,
C11,
C11,
CH3
CHコ
C■,
Ctl3
Clh
C!13
CH3
C11,
CH3
?CR (CI1 .) Co■CHzCH=ClhO
CH(CH:+)C(hcHzclI=cHzOCH(
CHz)CO■CH.CミCllOCH(Ctb)C(
hctl■C=CUOCII(CI1z)COzC h
HsOCR (CH 3) CO■C.HSOCII(
CH3)CO2CH!C.llsOCR(Clh)CO
zCHzCbtlsSCII■CO.ll
SCJCOzH
SCHzCO2cl++
sco,co■CH,
SCJCOzCglls
C113
C113
CIl:I
CL
CH3
C113
CH1
Cll3
CII
CH2
?CII■CO2CII (Clh) ZSCH2CO
■Cll(Cth)z
?CHzCOzCHzCH=CHz
SCII■COz(JIzCH=CHzSCIl2CO
2CII■C=CIl
SCHzC(hcIhcliicfl
SCII■CO2C6115
scozcozc6us
SCII■CO,CIl■CJs
SCHzC(hCHzCJs
?C11(CI+3)CO211
SCH (Cll :l) Co zCH zSCH
(CH i)CO■Clh
SCII (Cl 3) Co■C , II SSC
II (C}I z)CO■C z It sSCH(
CH3)CO■Cll(CH3)ZSCII(CFII
)Go■CI(CIl*)z?CII(CHi)COz
CHzCH =CHzSCH(CH3)CO■ClhC
}l=cHZSCH (CH3)CO■CH,CミCH
SCH(Cth)COzGHzC=CH0
S
0
S
?CII (Clli)COzCbllsSCH(C}
13)COZC6HS
SCH(CH:+)CO■CH2C61+SSCH(C
L)COzCIIzCdls■
lI
NHSOzCztls
N It S O z C z It sCOzCzl
ls
CO■CzHs
OCH (Clh) 2
0CH (CI+3) 2
0011■0三CH
OCR.C三CI+
OCII(Cth)CミC}l
OCII (CH 3) C=CI
SCH (CIl 3) Z
SCH(CH3)!
CH,
CI!
CHff
?CII■C=CO
SCHzCECH
SCH(CL)C=C}I
SCH(CH3)C=CH
OC11■CO■CH,
OC11■CO2CH3
SClhC(hcllz
SGHzC(hcflz
■
R.
cpzu
C113
C113
CH.
C11,
C113
Cll.
C11,
C113
C113
CH3
C113
Clh
CH3
C11,
CH.
C113
Clh
R1。OCHzCOzCllzCmiCI+OCH. CO■Cll■CmiCH OCH2CO2C6+15 0CH2CO2C6115 oct+. co■CHzCbH5 0CH2CO■CH2C1,H5 0CII (Ctl z)CO■■ OCII (Cl 3)CO■H OC11 (CI+3) COZCI1:10CH (CIl
:l) CO■CH, QC}l (CI13) CO■C . I+,OC1
1(C}13)CO, C2+15OCH(CH,)CO
2(Jl(CI13)20CH(CH:l)CO■Cl
l(CH3)2C113 C11, C11, C11, CH3 CHkoC■, Ctl3 Clh C! 13 CH3 C11, CH3? CR (CI1.) Co■CHzCH=ClhO
CH(CH:+)C(hcHzclI=cHzOCH(
CHz)CO■CH. CmiCllOCH(Ctb)C(
hctl■C=CUOCII(CI1z)COzC h
HsOCR (CH 3) CO■C. HSOC II (
CH3) CO2CH! C. llsOCR(Clh)CO
zCHzCbtlsSCII■CO. ll SCJCOzH SCHzCO2cl++ sco,co■CH, SCJCOzCglls C113 C113 CIl:I CL CH3 C113 CH1 Cll3 CII CH2 ? CII■CO2CII (Clh) ZSCH2CO
■Cll(Cth)z? CHzCOzCHzCH=CHz SCII■COz(JIzCH=CHzSCIl2CO
2CII■C=CIl SCHzC(hcIhcliicfl SCII■CO2C6115 scozcozc6us SCII■CO,CIl■CJs SCHzC(hCHzCJs ?C11(CI+3)CO211 SCH (Cll :l ) Co zCH zSCH
(CH i) CO■Clh SCII (Cl 3) Co■C , II SSC
II (C}I z)CO■C z It sSCH(
CH3)CO■Cll(CH3)ZSCII(CFII
)Go■CI(CIl*)z? CII(CHi)COz
CHzCH = CHzSCH(CH3)CO■ClhC
}l=cHZSCH (CH3)CO■CH,CmiCH
SCH(Cth)COzGHzC=CH0 S 0 S ? CII (Clli)COzCbllsSCH(C}
13) COZC6HS SCH (CH:+)CO■CH2C61+SSCH(C
L) COzCIIzCdls ■ lI NHSOzCztls N It S O z C z It sCOzCzl
ls CO■CzHs OCH (Clh) 2 0CH (CI+3) 2 0011■03CH OCR. C3CI+ OCII (Cth)CmiC}l OCII (CH 3) C=CI SCH (CIl 3) Z SCH (CH3)! CH, CI! CHff? CII■C=CO SCHzCECH SCH(CL)C=C}I SCH(CH3)C=CH OC11■CO■CH, OC11■CO2CH3 SClhC(hcllz SGHzC(hcflz ■ R. cpzu C113 C11 3 CH. C11, C113 Cll. C11, C113 C113 CH3 C113 Clh CH3 C11, CH. C113 Clh R1.
?1
11
]I
NIISO■C.H,
N}ISO■C.H,
CO■C.H,
CO2C2115
OCtl (CH 3) Z
OCR (Cll z) 2
0CH.CHCl1
ocozc=co
OCR (CH 3)C=ECI1
OCII (CH3)C=Cll
SCtl (CH3) z
SCH(CH3)2
SCHzc=ct+
SCH.CECH
SCH (CI+ 3)CBCI1
Re R9 RIG
C f OCIIzCOzCll3C I O
CIIZCO!CH3
?CH.CO■Cl3
SCH.CO■CH.
R6
CH,
CH,
C}1,
C113
Cl3
C11,
CH.
CI,
C113
CH3
CH3
Cl3
C11,
C113
C11,
CHff
Cll:+
?1。? 1 11 ]I NIISO■C. H, N}ISO■C. H, CO■C. H, CO2C2115 OCtl (CH 3) Z OCR (Cll z) 2 0CH. CHCl1 ocozc=co OCR (CH3)C=ECI1 OCII (CH3)C=Cll SCtl (CH3) z SCH(CH3)2 SCHzc=ct+ SCH. CECH SCH (CI+ 3)CBCI1 Re R9 RIG C f OCIIzCOzCll3C I O
CIIZCO! CH3? CH. CO■Cl3 SCH. CO■CH. R6 CH, CH, C}1, C113 Cl3 C11, CH. CI, C113 CH3 CH3 Cl3 C11, C113 C11, CHff Cll:+? 1.
NHSO2CZllS CO■C.H, CO■C . II , OCH (Cll 2) 2 0CII (CB :l) ! OCHZCミCI1 OCH.C:CH OCII(CH3)C三CI OCII(CH3)C=CII SCH (CIl:l) 2 SCII (CH 3) 2 SCII■C=CU SCH2C=(JI SCH(CH3)C壬Cll SCII (CH:+)C=CH OCH2CO■C113 0CHzCOzCtl+ CH3 11 11 ■ CF.ll CH3 CH3 CH. Cl3 CL CH. 1?+o ?CII■COzCHz SCFlzCOzCHz ? cozczos ocozc=cu H ■ ■ NHSO■C 2 II S NHSO■CzHs CO■C z If s CO■C2H, R. C11, CIl. CH3 CH. CI. C11, C{1, C113 C!13 Clh CH. Clh CH, CI! R1。NHSO2CZllS CO■C. H, CO■C . II, OCH (Cll 2) 2 0CII (CB:l)! OCHZC MiCI1 OCH. C:CH OCII(CH3)C3CI OCII(CH3)C=CII SCH (CIl:l) 2 SCII (CH 3) 2 SCII■C=CU SCH2C=(JI SCH (CH3)C Cll SCII (CH:+)C=CH OCH2CO■C113 0CHzCOzCtl+ CH3 11 11 ■ C.F. ll CH3 CH3 CH. Cl3 C.L. CH. 1? +o ? CII■COzCHz SCFlzCOzCHz ? cozczos ocozc=cu H ■ ■ NHSO■C 2 II S NHSO■CzHs CO ■ C z If s CO■C2H, R. C11, CIl. CH3 CH. C.I. C11, C{1, C113 C! 13 Clh CH. Clh CH, CI! R1.
OCII (CH3) z OCR2C二CH OCR2C=CH OCR(CH3)CミCH OCR(Clh)C壬Cll SCII (CH 3) Z SCH(CH3)Z SCHzCECH SCH!C=CI1 SCtl (CH *)C=CH SCH (CIl :l) c=cu OCHzCOzCH:+ OCH2CO2Cll3 ?CII■CO■CH, RIG ? !1 11 NHSO■czus NHSO■C . I1 , CO■C2H% CO■C28% OCH (Cllz) z OCR (Clh) z OCR2C二CH OCR2C.:CH OCII (Cll z)C=CH OCH (C}l ff) CECH C11, C113 ?CH (Cll 3) ! SCII■C三CH SCII■C三CH SCtl (CI+)C=CH SCII(Clli)C=CII OC11■CO2CIl:1 0C11■CO,CI. ?O■ ?CII■COzCHs SCII■CO2CIl3 ■ ■ R. p, R. R9 R1。OCII (CH3) z OCR2C2CH OCR2C=CH OCR(CH3)CmiCH OCR(Clh)C壬Clll SCII (CH 3) Z SCH(CH3)Z SCHzCECH SCH! C=CI1 SCtl (CH *)C=CH SCH (CIl:l) c=cu OCHzCOzCH:+ OCH2CO2Cll3 ? CII CO CH, R.I.G. ? ! 1 11 NHSO■czus NHSO■C. I1, CO■C2H% CO■C28% OCH (Cllz)z OCR (Clh)z OCR2C2CH OCR2C. :CH OCII (Cll z) C=CH OCH (C}l ff) CECH C11, C113 ? CH (Cll 3)! SCII■C3CH SCII■C3CH SCtl (CI+)C=CH SCII (Clli)C=CII OC11■CO2CIl:1 0C11 ■ CO, CI. ? O■ ? CII■COzCHs SCII■CO2CIl3 ■ ■ R. p, R. R9 R1.
C11,
F
F
?O■
11
(以下、
余白)
X
0
第3
6表
CH.
CH3
?1
lI
Co2H
CO■11
COZCI+3
CO■C{13
CO■C 2 II 5
CO2C2115
CO■Cll(CI13).
COzCH (CH3) z
coz−○
co,−(]
CL
C11,
CHi
C113
C11,
CH,
CI,
C113
CH3
Cl{.
CH.
CH,
C}I,
(Jl,
C■3
CI.
?IICOCII:I
NHCOzClh
NIICO■CR,
NHSO2CII:I
NHSO■C113
NHSO■C 2II 5
NIISOzCzHs
CO■H
CO!}I
COzCIh
Co2CH,
CO■C2H,
CO2C2}1,
CO2CH (Cl:l) z
C(hcJl(Clh) 2
co.−(]
CH3
CH’s
cHi
CHs
CH.
CM.
C113
Clh
Cll:I
C11,
Cll+
CIl3
C}l,
CHx
CH3
CIz
CH3
?O■Cll■co=coz
CO,C}12C}I=CII■
CO■CH tCミCH
CO■CH ,CミCH
C(hCJs
COzCbHs
CO2CJCills
CO2ClI■C . II ,
0■
OH
OCH.
OCI13
0CJs
OCzlls
OCR(CH3)!
OCH(CH3)2
0−CI
CH.
CI+.
CHx
CH3
CH,
CIl3
CH3
C11,
CH3
CH.
C113
Clh
CHs
CH,
CI3
?−CI
O−O
O−0
0CHzCH=CHz
OCI{2Ctl=CI1■
OCH ,C : CH
OCH ,C El: OH
QC}l (Ctlz) CミCII
OCII(CH:I)CミCFI
SH
SH
SCH 3
SCH 3
SC.H,
SC.Hs
CH,
CH.
CH3
C!1,
CI+3
CI,
CI,
C11,
CI{.
CI,
CHi
CH,
CH3
CH3
CH,
?CII (Cll :l) z
S−CI
S−C+
S−0
8−0
SCII■(Jl=CHt
SCHtCH−CIl■
SCH,C:Cl+
SGHzCE(41
SCII (CH 3) C E CllSCI{ (
CH 3) C E CHOCH,CO■H
OCRzCO■N
OCHZCO2CI3
0CHzCOzCHz
?1。C11, FF? O ■ 11 (hereinafter referred to as margin) X 0 3rd 6th table CH. CH3? 1 lI Co2H CO■11 COZCI+3 CO■C{13 CO■C 2 II 5 CO2C2115 CO■Cll (CI13). COzCH (CH3) z coz-○ co, -(] CL C11, CHi C113 C11, CH, CI, C113 CH3 Cl{. CH. CH, C}I, (Jl, C■3 CI. ?IICOCII:I NHCO zClh NIICO■CR, NHSO2CII:I NHSO■C113 NHSO■C 2II 5 NIISOzCzHs CO■H CO!}I COzCIh Co2CH, CO■C2H, CO2C2}1, CO2CH (Cl:l) z C(hcJl(Clh) 2 co. -(] CH3 CH's cHi CHs CH. CM. C113 Clh Cll:I C11, Cll+ CIl3 C}l, CHx CH3 CIz CH3 ?O■Cll■co=coz CO, C}12C}I=CII■ CO ■ CH tCmiCH CO■CH ,CmiCH C(hCJs COzCbHs CO2CJCills CO2ClI■C . II , 0■ OH OCH. OCI13 0CJs OCzlls OCR(CH3)! OCH(CH3)2 0-CI CH. CI+. CHx CH3 CH , CIl3 CH3 C11, CH3 CH. C113 Clh CHs CH, CI3 ?-CI O-O O-0 0CHzCH=CHz OCI{2Ctl=CI1■ (Ctlz) C Mi CII OCII (CH: I) C Mi CFI SH SH SCH 3 SCH 3 SC.H, SC.Hs CH, CH. CH3 C!1, CI+3 CI, CI, C11, CI{. CI, CHi CH, CH3 CH3 CH, ?CII (Cll :l) z S-CI S-C+ S-0 8-0 SCII■(Jl=CHt SCHtCH-CIl■ SCH,C:Cl+ SGHzCE(41 SCII (CH 3) C E CllSCI{ (
CH 3) C E CHOCH,CO■H OCRzCO■N OCHZCO2CI3 0CHzCOzCHz ? 1.
OC11■COzCzlls
OCHzC(hCH(Clh)z
OCH2COZCH(CH3)2
?C11■CO■CHzCH=CllzOCH,CO■
CHzCH=C}lx
OCH 2C0 2CII■C=CIIOCH2COZ
CIl■CECH
OCH,CO■Chis
OCR2CO■C.H,
OCH2CO■CHzCJs
OCHzCOzCtl■C.Hs
OCH (CIl ff) CO■■
Cth
CI.
C11,
?CII (Cll ff) CO illOCH(C
Hs) COzCH+
OCR(CHs)COtCHs
OCI{(CL)COzCglls
OCI{(CH3)COtC!H,
OCR(CHz)COzCH(CH2) !OCR(C
I+)CO■CH(Clls)zCl
Cl
Cl
Cl
?CR(Clls)CO■−O
OCH(Clh)CO■一〇
OCR(CH3)CO■−O
OCH(Cl(s)Cot−0
0
S
0
S
?CH(CHs)CO■CHzCH=CllgOCH(
Ctl*)COzCthCII=CI%■OCH(CI
+3)CO■CH.CミClIOCI(CIl:I)C
O■co,c=coC113
C!1,
C113
C113
?CII (CI13)CO■C , II ,OCH
(CHz)CO■CH!C.H,OCH (Ctlz
)COzCHzCiHsSCH2CO■{I
SCllzC(hll
SCI12CO■CR,
SCH,CO■C113
SCI{2C02C.t+,
SCH2CO!C2HS
SCHzC(hcH(CH*)z
SCH.CO■Cll (Cll z) 2?CIl2
CO2−(I]
SCHZCO■−C
SCIIgcoz −O
S山co 2−(II)
0
S
0
S
?CII■COgCHzCH=CHz
0
Cth
?1。OC11■COzCzlls OCHzC(hCH(Clh)z OCH2COZCH(CH3)2 ?C11■CO■CHzCH=CllzOCH,CO■
CHzCH=C}lx OCH 2C0 2CII■C=CIIOCH2COZ
CIl■CECH OCH,CO■Chis OCR2CO■C. H, OCH2CO■CHzCJs OCHzCOzCtl■C. Hs OCH (CIl ff) CO■■ Cth CI. C11, ? CII (Cll ff) CO illOCH (C
Hs) COzCH+ OCR(CHs)COtCHs OCI{(CL)COzCglls OCI{(CH3)COtC! H, OCR(CHz)COzCH(CH2)! OCR(C
I+)CO■CH(Clls)zCl Cl Cl Cl ? CR(Clls)CO■-O OCH(Clh)CO■10OCR(CH3)CO■-O
Ctl*)COzCthCII=CI%■OCH(CI
+3) CO■CH. CmiClIOCI(CIl:I)C
O ■ co, c = coC113 C! 1, C113 C113? CII (CI13) CO■C, II, OCH
(CHz)CO■CH! C. H, OCH (Ctlz
)COzCHzCiHsSCH2CO■{I SCllzC(hll SCI12CO■CR, SCH,CO■C113 SCI{2C02C.t+, SCH2CO!C2HS SCHzC(hcH(CH*)z SCH.CO■Cl l (Cll z) 2?CIl2
CO2-(I) SCHZCO■-C SCIIgcoz -O S mountain co 2-(II) 0 S 0 S ?CII■COgCHzCH=CHz 0 Cth ?1.
SCIIzCOzClbCll=CIIzSCH.CO
■CH.CECH
SCI1 ,Co■CH ,C三CH
SCH2CO■C.H,
SCH.CO■C . I1 ,
SCH,CO■CHtCJIs
SCH.CO■CHzChHs
SCH(C}Is)COtH
SCII (CH 3) CO■■
SCH(CH+)C(hcll+
SCH(CHs)CO■C11,
SCII(CHz)CO■C.Hs
SCII(Cllz)COzCzHs
SCH(C}lz)C(hcH(CHs)zSCH(C
l:l)Co■co(cut)zSCH(CHff)C
O■一〇
C2
SCH (Cll 3)Co!−0
S
Clh
Cll.
CH.
C113
CI13
CI{3
C113
C113
CH3
CH3
CH3
C113
CH3
CHff
R9
RIG
X
?CH(CH3)CO■CH2Cll・CH2SCH(
CH3)COzCllzCll=CHzSCII (C
H3)CO■CH2C : CHSCH (CH3)C
OzCII■C=CI+SCH (CH :l)Co■
C . 11 ,SCH (CIL+)CO■C .
I1 ,SCII (CH:+)CO■ClI■C .
11 ,SCH (CHz)COzCtl■C 6I
+ ,II
H
NHSOzCJs
NIISO■C.H,
COzCzHs
CO■C.H,
R6
CII+
CHff
CH.
C{1,
C]13
CH,
CH,
C{13
C113
C11,
C1{3
C■,
CH.
CH3
?1。SCIIzCOzClbCll=CIIzSCH. C.O.
■CH. CECH SCI1, Co■CH, C3CH SCH2CO■C. H, SCH. CO■C. I1, SCH, CO■CHtCJIs SCH. CO■CHzChHs SCH(C}Is)COtH SCII (CH 3) CO■■ SCH(CH+)C(hcll+ SCH(CHs)CO■C11, SCII(CHz)CO■C.Hs SCII(Cllz)COzCzHs S CH(C }lz)C(hcH(CHs)zSCH(C
l:l)Co■co(cut)zSCH(CHff)C
O■10C2 SCH (Cll 3)Co! -0 S Clh Cl. CH. C113 CI13 CI{3 C113 C113 CH3 CH3 CH3 C113 CH3 CHff R9 RIG X? CH(CH3)CO■CH2Cll・CH2SCH(
CH3) COzCllzCll=CHzSCII (C
H3)CO■CH2C: CHSCH (CH3)C
OzCII■C=CI+SCH (CH:l)Co■
C. 11, SCH (CIL+)CO■C.
I1, SCII (CH:+)CO■ClI■C.
11 ,SCH (CHz)COzCtl■C 6I
+ , II H NHSOzCJs NIISO■C. H, COzCzHs CO■C. H, R6 CII+ CHff CH. C{1, C]13 CH, CH, C{13 C113 C11, C1{3 C■, CH. CH3? 1.
OCII (Cll 3) !
OCII (Clh) z
OCH!C三Cll
ocuzc=co
OCR (CH3)C E CH
OCII (Cll :l)C三CH
SCII (CH3) z
SCH (Cll 3) 2
SCII■C三CH
SC82C:CH
SCH(Clh)C三CIl
SCH(CHs)C:CH
OCH2CO■C113
0C{1■CO■C113
CH.
CI.
H
H
CF2+1
CIl1
CI+3
CI3
CH2
CH3
CH.
C11,
C11,
CH,
CH.
RIG
?CII■CO■C]13
?
CO■CH.
11
1l
H
NHSO■C.H,
NHSO2CZHS
CO■C 2 II S
CO2C2HS
OCH (CH :l) !
OCH (CI13) z
OC11■CECI+
OCH2C三CH
CH,
CH3
?1凰O
OCII (Cll 3) C−CllSCtl(CM
:+)z
SCII (CH 3) z
SCH2C三CH
SCH21CH
SCH(CH3)C三CI
SCH (CH 3) C E CllOCIIgC(
hcH3
0C11■Co2CH,
SCH2C02CI+3
SCHzC(hCH:+
?1
11
CO■CgHS
■
■
11
NHSO■C2115
NIISO■C z If s
CO■C 2 II ,
CO■CzHs
OCII (Cll 3) 2
0CI{(Cl:1)2
0CH2CEClI
O011■C三CII
OCII(Ctl:+)C
OCH(CH3)C
SC}I(CH*h
C]13
C113
CH.
C11,
CI3
CH3
?CII■C=CI+
scttzc二CH
SCH(C}l.)CミCll
SCH(Clh)CミC}l
OC11■CO■CHク
OCtlzCOzCH*
?co,co.−(II]
OCH.CO■−O
?CH2CO■CR,t
?cozco■CH3
?CII■COt−○
SC!l zcOz−(T]
■
?O■CHI
R6
CF!+1
C■,
CL
0113
C1{3
C113
Cll:I
C113
CI13
C]1,
C113
C113
C}I:I
CI13
CH3
C113
Cll:+
C113
?,。OCII (Cll 3)! OCII (Clh) z OCH! C3Cll ocuzc=co OCR (CH3)C E CH OCII (Cll :l)C3CH SCII (CH3) z SCH (Cll 3) 2 SCII■C3CH SC82C:CH SCH (Clh)C3CIl SCH ( CHs)C:CH OCH2CO■C113 0C{1■CO■C113 CH. C.I. H H CF2+1 CIl1 CI+3 CI3 CH2 CH3 CH. C11, C11, CH, CH. RIG? CII■CO■C]13? CO■CH. 11 1l H NHSO■C. H, NHSO2CZHS CO■C 2 II S CO2C2HS OCH (CH:l)! OCH (CI13) z OC11■CECI+ OCH2C3CH CH, CH3? 1 凰O OCII (Cll 3) C-CllSCtl (CM
:+) z SCII (CH 3) z SCH2C3CH SCH21CH SCH (CH3)C3CI SCH (CH 3) C E CllOCIIgC (
hcH3 0C11■Co2CH, SCH2C02CI+3 SCHzC (hCH:+ ?1 11 CO■CgHS ■ ■ 11 NHSO■C2115 NIISO■C z If s CO■C 2 II , CO■CzHs OCII (Cll 3) 2 0CI {(Cl:1 )2 0CH2CEClI O011■C3CII OCII(Ctl:+)C OCH(CH3)C SC}I(CH*h C]13 C113 CH. C11, CI3 CH3 ?CII■C=CI+ scttzc2CH SCH(C} l.)CmiCll SCH(Clh)CmiC}l OC11■CO■CHkuOCtlzCOzCH* ?co,co.-(II) OCH.CO■-O ?CH2CO■CR,t ?cozco■CH3 ?CII ■ COT -○ SC! L ZCOZ- (T] ■? O ■ CHI R6 CF! +1 C. C113 CLL :+ C113?,.
11
H
■
NHSOzCJs
NHSO■C2115
COzCJs
CO■C2O,
OCII (Cth) z
OCH(C}lsh
OCR 2C:CI
OCII■C”l:CI
OCR (Cll :I) C三CI1OCII (C
ll 3) C三CI+SCH(CH3)2
SCII (Cll :+) z
SCIhC壬Cl+
SCII,C三CH
SCH(Clh)C−:CH
C113
C113
?IO
SCII (Cll :l) C E CllOCHz
C(hcHz
OCH■COzCI’h
SCHzCOzClh
?CII■COzCH:+
?1。11 H ■ NHSOzCJs NHSO■C2115 COzCJs CO■C2O, OCII (Cth) z OCH(C}lsh OCR 2C:CI OCII■C”l:CI OCR (Cll :I) C3CI1OCII (C
ll 3) C3CI+SCH(CH3)2 SCII (Cll :+) z SCIhC壬Cl+ SCII, C3CH SCH(Clh)C-:CH C113 C113 ? IO SCII (Cll :l) C E CllOCHz
C(hcHz OCH■COzCI'h SCHzCOzClh ?CII■COzCH:+ ?1.
COzCzlls
CO2C211S
OCII (Clh) z
OCR(CH3)z
OCR.CミCll
OCHZC三CH
OCII(Ctl3)CECII
OCII(CH3)C:ECII
SCII (CI :l) 2
SCII (Cll 3) 2
SCII,C E Cl+
SCH.CECH
SCII (CIl:l)C =CllSCII (C
I+ 3) C E CHOCH2CO■Cll3
ocnzco■C113
C11,
CH.
11
■
F
F
?O■ SCH.CO■CH.
NO■ scHzco■Cl,
11
11
CI,
■
F
F
F
F
F
?O■ ■
NO■ ■
NO■ H
第3−7表
CI,
?1
H
CO211
CO■]I
CO■CllJ
CO■C113
CO■C . I+ ,
CO2C2HS
CO■Cll (Cll s) z
CO2Cll(CH:I) 2
?O■一〇
?llCOClh
NHCO■CH3
NHCO,CH,
NHSO2CH3
NIISO■CI,
NIISO2C211S
NIISO■C 2 11 S
CO■H
Cozl{
CO■C113
CO■C]13
COzG,++,
CO2C28S
CO■CH(CH3)z
COzCll (CHi) z
?OzCllzCIl=CIIz
CO!CIl2Ctl=Cllz
COzCHzCECH
cOtcHzc=cH
CO■C b It s
CO■C.H,
COzCIIzCJs
C(hCHzCJs
011
0H
OCH !
0CH!
0C2Hs
oczos
OCII(Clli)z
OCH(CI!)t
C1{3
Clh
C113
C11,
CIl3
Clh
CII3
C113
Clh
C■,
Clh
Cll3
RIG
?C11■C It = C It■
OCHzCH=CII■
OCH2C三CII
OCI2C=CIl
OCII (CH 3)C
OCtl(Cl{3)C
Sll
Sl+
SCII:I
SCH3
SC,II,
SC,U,
CI+
Cll
C11,
CIl,
C113
C113
CH.
CI.
CI3
CH.
CH3
Cl3
C11,
SCII(Clls)z
?CII■CH=CIh
scuzcu=cn■
SCH2C:ECH
SGHzC:ECH
SCII(CH3)CECH
SCH(Cth)C”::CH
OCHtCOzH
OCHzCOJ
OCHiCOzCH3
0C11■COtCHi
CH.
C11,
C11,
CI.
Clh
Cl,
CH3
CH.
CI13
?IG
OC11■CO■C . I1 ,
OCll2CO。CI(CH3)Z
OCHzCO■CH(CH:l)2
?ct+gco■ClI■C It = C II■O
011■CO■Cll■C I = C H■OCHz
C(hcIIzc三Cll
OCHzC(hCHzC−CH
OCII■C(hCJs
OCHzC(hcJIs
OCH2CO■ClhCJs
OCH2CO■CH!C.HS
OCII (CHa)COzH
?1。COzCzlls CO2C211S OCII (Clh) z OCR (CH3) z OCR. Cmi Cll OCHZC3 CH OCII (Ctl3) CECII OCII (CH3) C: ECII SCII (CI :l) 2 SCII (Cll 3) 2 SCII, C E Cl+ SCH. CECH SCII (CIl:l)C = CllSCII (C
I+ 3) C E CHOCH2CO■Cll3 ocnzco■C113 C11, CH. 11 ■ F F? O ■ SCH. CO■CH. NO ■ scHzco ■ Cl, 11 11 CI, ■ F F F F F ? O ■ ■ NO ■ ■ NO ■ H Table 3-7 CI, ? 1 H CO211 CO■] I CO■CllJ CO■C113 CO■C . I+ , CO2C2HS CO■Cll (Cll s) z CO2Cll(CH:I) 2 ? O■10? llCOClh NHCO■CH3 NHCO,CH, NHSO2CH3 NIISO■CI, NIISO2C211S NIISO■C 2 11 S CO■H Cozl{ CO■C113 CO■C] 13 COzG, ++, CO2C28S CO■CH(CH3)z COzCll (CHi)z ? OzCllzCIl=CIIzCO! CIl2Ctl=Cllz COzCHzCECH cOtcHzc=cH CO■C b It s CO■C. H, COzCIIzCJs C(hCHzCJs 011 0H OCH ! 0CH! 0C2Hs oczos OCII(Clli)z OCH(CI!)t C1{3 Clh C113 C11, Cll3 Clh CII3 C113 Clh C■, Clh Cll3 RIG?C11■C It = C It OCHzCH=CII 113 CH.CI .CI3 CH. CH3 Cl3 C11, SCII(Clls)z ?CII■CH=CIh scuzcu=cn■ SCH2C:ECH SGHzC:ECH SCII(CH3)CECH SCH(Cth)C”::CH OCHtCO zH OCHzCOJ OCHiCOzCH3 0C11■COtCHi CH . C11, C11, CI. Clh Cl, CH3 CH. CI13 ?IG OC11■CO■C .I1 , OCll2CO.CI(CH3)Z OCHzCO■CH(CH:l)2 ?ct+gco■ClI■C It = C II ■O
011■CO■Cll■C I = C H■OCHz
C(hcIIzc三Cll OCHzC(hCHzC-CH OCII■C(hCJs OCHzC(hcJIs OCH2CO■ClhCJs OCH2CO■CH!C.HS OCII (CHa)COzH ?1.
OCII(Clb)CO■I1
0CH (Clh)COzCHz
OCH(Clh)CO■CH3
0CH (CH 3)CO■C2+1,OCR (Cl
l a)CO■C ! II SQC)I(CHa)C
(hcH(CHs)zOCII (Cl :l) CO
■Cl(CI+3)2Cl
CI2
?CH(CH3)CO■−C
OCH (Clh)Co■一〇
0
S
?CH(CH3)CO■CHzCII=CHzOCII
(CH3)CO■CH2CH=CII■OCII (
Clh)C(hclhcヨCIIOCI1(CI+3)
CO2CH2CECHOCH(CH3)CO■C6HS
R.
CH3
CH,
CH.
CL
C11,
CH3
C113
CH.
Clh
C11,
C11,
CH3
?I0
0CII(CH:+)C(hcbllsOCH (CI
1 .) CO■CH.C6H,OCH (CH :l
)Co■CH.C.H,SCH,CO■11
SCII■C02H
SCII.CO■Cl3
SCH■CO.CHff
SCHZCO■C . I+ ,
SCH2CO■Czlls
SGHzCOzCH(CH3)z
SCII■CO■co (c++ 3) 2?CII■
CO■Cll■CH=CH2O
CI,
CH,
C]13
CH,
C11,
CH,
CHi
Cl,
C1]3
CH3
Cl{,
CI,
CH.
CH3
C113
C11,
CH,
?CII■CO■ClI■CIl・CIl2SCHtC
O2CH2CECFI
SCII2CO2CH,C : CllSCII■CO
zCJs
SCJCO2CaHs
SCH2CO■ClI■C.H5
SCH2CO2CII■C.IIS
SCII(CH.)CO.l+
SCII (CH 3) CO■H
SCtl(Clh)C(hcHi
SCH(CHs)CO■C11,
SCH (CH.) CO■C 2II ,SCII(
CHi)COzCJs
SCII(CH3)COzCH(CH:+) 25CI
I(CH3)CO■CH(CH3)2SCH(CH3)
COg−<I]
Cl
SCH(CHz)COz−0
S
C113
C113
C11,
C113
C113
CH3
C113
C113
C11,
CI−13
C113
C113
C113
C11,
R9
R,。OCII(Clb)CO■I1 0CH (Clh)COzCHz OCH(Clh)CO■CH3 0CH (CH 3)CO■C2+1,OCR (Cl
l a) CO■C! II SQC)I(CHa)C
(hcH(CHs)zOCII (Cl :l) CO
■Cl(CI+3)2Cl CI2? CH(CH3)CO■-C OCH (Clh)Co■100 S? CH(CH3)CO■CHzCII=CHzOCII
(CH3)CO■CH2CH=CII■OCII (
Clh)C(hclhcyoCIIOCI1(CI+3)
CO2CH2CECHOCH(CH3)CO■C6HS R. CH3 CH, CH. CL C11, CH3 C113 CH. Clh C11, C11, CH3? I0 0CII(CH:+)C(hcbllsOCH (CI
1. ) CO■CH. C6H,OCH (CH:l
)Co■CH. C. H, SCH, CO■11 SCII■C02H SCII. CO■Cl3 SCH■CO. CHff SCHZCO■C. I+, SCH2CO■Czlls SGHzCOzCH(CH3)z SCII■CO■co (c++ 3) 2? CII■
CO■Cll■CH=CH2O CI, CH, C]13 CH, C11, CH, CHi Cl, C1]3 CH3 Cl{, CI, CH. CH3 C113 C11, CH, ? CII■CO■ClI■CIl・CIl2SCHtC
O2CH2CECFI SCII2CO2CH,C: CllSCII■CO
zCJs SCJCO2CaHs SCH2CO■ClI■C. H5 SCH2CO2CII■C. IIS SCII (CH.) CO. l+ SCII (CH 3) CO ■ H SCtl (Clh) C (hcHi SCH (CHs) CO ■ C11, SCH (CH.) CO ■ C 2II , SCII (
CHi) COzCJs SCII (CH3) COzCH (CH:+) 25CI
I(CH3)CO CH(CH3)2SCH(CH3)
COg-<I] Cl SCH (CHz) COz-0 S C113 C113 C11, C113 C113 CH3 C113 C113 C11, CI-13 C113 C113 C113 C11, R9 R,.
X
?CII (Cll 3)Co■ClI■CIl=CH
.SCH(CH3)CO■CH2CH=CI2SCII
(Cll z)CO■Cll■C三CllSCH (
CI13)CO■ClI■CECI+SCII (CI
+3)CO■C . II 5SCII (CI13)
CO■C&+15SC+1(CI+3)CO■CIIz
CbllsSCH(CllJ)C(hcIIzcJs■
H
NHSO■C2H,
NIISO■CzHs
CO■C 2I+ 5
CO2C2115
CI.
CI,
C11,
?,。X? CII (Cll 3)Co■ClI■CIl=CH
.. SCH(CH3)CO■CH2CH=CI2SCII
(Cll z)CO■Cll■C3CllSCH (
CI13) CO■ClI■CECI+SCII (CI
+3) CO■C. II 5SCII (CI13)
CO■C&+15SC+1(CI+3)CO■CIIz
CbllsSCH(CllJ)C(hcIIzcJs■ H NHSO■C2H, NIISO■CzHs CO■C 2I+ 5 CO2C2115 CI. CI, C11, ?,.
OCII (Clli) 2 0CH(Cll+)z OCH2C−:Cl1 OC11■CECI+ OCR(CI+3)C=CII OCR(CHi)CECH SCII(CH3)! SCH(CHz)z SCH.CECH scuzc=co SC}l(CH3)CECH SCH(CHff)CEC!1 0CHzCOzCI3 0C11■CO.CHユ ?CH .CO■−C SGHzCOzCI’l3 CH3 C113 R1。OCII (Clli) 2 0CH(Cll+)z OCH2C-:Cl1 OC11■CECI+ OCR(CI+3)C=CII OCR(CHi)CECH SCII (CH3)! SCH(CHz)z SCH. CECH scuzc=co SC}l(CH3)CECH SCH(CHff)CEC! 1 0CHZCOzCI3 0C11■CO. CH Yu ? CH. CO■-C SGHzCOzCI’l3 CH3 C113 R1.
?CII■C02CIh
?
CO■C113
H
■
H
NHSO2C211S
NHSO■CzHs
CO.CZl1,
CO2C,II,
OCH(CH3)2
QC}l(CH3)2
0011■CECI+
OC11■C:CH
OCH(CH3)C
CI,
OCII (Cll 2) C E CHSCtl(C
Ill)z
SC}l(Clls)z
SCH,CミCH
SCll2C:CH
SCH(Cllz)CミCll
SCII (Ctl3) C三CIl
OCHzCOzCllz
OCHzCOtCIIs
?CHzCOt−0
0C82CO■一〇
?CH2CO■CH3
SCH2CO■C11,
?CH2CO■−C
SCFI!CO■−○
R.
H
11
■
CF2H
C113
C113
C}l,
CH3
C113
C11,
C1]3
CH3
CI+.
C113
C113
C!13
Clh
?l+1
11
11
CO■C113
■
11
■
NHSO2CZI+5
NlISO2C2HS
COzCtHs
CO■C2HS
OCH (Cll :+) z
(IcII(Cl:l)2
0011■C三Cl1
OC11■CECI+
OCII (Cll :l)CミCIIOCI (CH
3) CミCH
SCII (CH3) z
C}13
CH3
CH3
C11,
C11,
CI13
?CII■CECI1
SCII■C−ECI1
SCII (Cll :I)C E CllSCH(C
Il:l)C=CH
OCHzC(hclb
OC11■CO■Clh
?CH2CO■一C
ocozcoz〜C
SGHzCOzCH+
SCl12C(hCH3
?CH2CO■一C
SCHzCOz−0
■
COzCzlls
CF2H
CH3
C11,
CIl3
CH3
C113
Cll.
CH3
C11,
CIl,
Cll,
CL
CH3
CH3
C11,
CH3
CH3
?1
■
11
NHS(hCJs
NHSO,C21ts
CO■C 2 II S
CO*CzHs
OCH(CH3)2
0CH (Cll 3) z
OCfl 2C E Cll
OC11■CEECI+
OCfl (Cll 3)C E CIOCH(Cll
3)CミCl+
SCII(Cll:l) t
SCH(CH3)2
SCH,C三Cl+
SCH2C三CI+
C11,
C11,
CII+
? I SCII(Clh)CECII S
CI OCII■C(hCL OCf
OCII■CO■CH3 SCI−
h
C113
F Cff
F (J
?CH2CO■一C
OCII■co,−(]
CH3
Clh
? CI SCII■CO■C113F
C I SCHzC(hCH:+CIl:1
CL
■
lI
CH3
CH3
CHff
F Cffi
F Ci!.
?CII■co2−(]
sc++zco■一〇
■
H
■
11
NllSOzCzHs
CIlJ
?O2C2H,
OCtl (CIl3) z
OCR (Cll 3) Z
OC11■C:CI1
OC1I■CECH
OCII(CHz)C三CIl
OCII(Cl,)CミC11
SCII (Cll :+) z
SCII (CI13) Z
SCII■C=CI1
SCII■CECI
SCH(CI+3)CミCIl
SCII(CI+3)C三CH
OC11■COzCHi
OCH.CO■CH3
?C11■co−(1
CI.
N(h
?CII!CO■一〇
C11,
? NO■ SCII■CO2CI13F
NO■ SCII■COzCHsC1]3
CIL+
Clh
F NOx
F Not
?CH,CO■−G
scLco!−(l]
■
1{
■
(以下、
余白)
第3
8表
C113
C113
?1
11
CO■11
CO■11
CO2CH3
CO■CH3
CO■C2115
CO■C 2I1 5
CO■Cl(CIIJz
COzCIl(Cll+) 2
CO2−CI
CO2−(1
?1。? CII■C02CIh? CO■C113 H ■H NHSO2C211S NHSO■CzHs CO. CZl1, CO2C,II, OCH(CH3)2 QC}l(CH3)2 0011■CECI+ OC11■C:CH OCH(CH3)C CI, OCII (Cll 2) C E CHSCtl(C
Ill)z SC}l(Clls)z SCH,CmiCH SCll2C:CH SCH(Cllz)CmiCll SCII (Ctl3) C3CIl OCHzCOzCllz OCHzCOtCIIs ? CHzCOt-0 0C82CO■10? CH2CO■CH3 SCH2CO■C11, ? CH2CO■-C SCFI! CO■-○ R. H 11 ■ CF2H C113 C113 C}l, CH3 C113 C11, C1]3 CH3 CI+. C113 C113 C! 13 Clh? l+1 11 11 CO■C113 ■ 11 ■ NHSO2CZI+5 NlISO2C2HS COzCtHs CO■C2HS OCH (Cll :+) z (IcII(Cl:l)2 0011■C3Cl1 OC11■CECI+ OCII (C ll :l)Cmi CIIOCI (CH
3) C Mi CH SCII (CH3) z C}13 CH3 CH3 C11, C11, CI13? CII■CECI1 SCII■C-ECI1 SCII (Cll :I)C E CllSCH(C
Il:l) C=CH OCHzC(hclb OC11■CO■Clh ?CH2CO■1C ocozcoz~C SGHzCOzCH+ SCl12C(hCH3 ?CH2CO■1C SCHzCOz-0 ■ COzCzl ls CF2H CH3 C11, CIl3 CH3 C113 Cll. CH3 C11, CIl , Cll, CL CH3 CH3 C11, CH3 CH3 ?1 ■ 11 NHS(hCJs NHSO,C21ts CO■C 2 II S CO*CzHs OCH(CH3)2 0CH (Cll 3) z OCfl 2C E Cll OC 11■CEECI+ OCfl (Cll 3) C E C I O C H (Cll
3) CmiCl+ SCII(Cll:l) t SCH(CH3)2 SCH,C3Cl+ SCH2C3CI+ C11, C11, CII+? I SCII (Clh) CECII S
CI OCII ■C (hCL OCf
OCII CO CH3 SCI-
h C113 F Cff F (J ?CH2CO■1C OCII■co,-(] CH3 Clh ? CI SCII■CO■C113F
C I SCHzC(hCH:+CIl:1 CL ■ lI CH3 CH3 CHff F Cffi F Ci!. ?CII■co2-(] sc++zco■10■ H ■ 11 NllSOzCzHs CIlJ ?O2C2H, OC tl (Cll3) z OCR (Cll3 ) Z OC11■C:CI1 OC1I■CECH OCII(CHz)C3CIl OCII(Cl,)CmiC11 SCII (Cll :+) z SCII (CI13) Z SCII■C=CI1 SCII■CECI SCH(CI+3) C MiCIl SCII (CI+3)C3CH OC11■COzCHi OCH.CO■CH3 ?C11■co-(1 CI. N(h ?CII!CO■10C11, ? NO■ SCII■CO2CI13F
NO■SCII■COzCHsC1]3 CIL+ Clh F NOx F Not? CH, CO■-G scLco! -(l) ■ 1 { ■ (hereinafter, margin) 3rd 8 Table C113 C113 ?1 11 CO■11 CO■11 CO2CH3 CO■CH3 CO■C2115 CO■C 2I1 5 CO■Cl(CIIJz COzCIl(Cll+) 2 CO2-CI CO2-(1?1.
NllCOCl+3 NIICO■C113 NIICOZCIh NIISO■CH3 N II S O。CL NHSO■CZHS NHSO■C 2 11 5 CO■■ CO■II CO2(JI3 CO■CL COzCzlls COzCzlls CO2Cll (CH3) z CO■Cll(C}+3)2 ?IG CO■ClI■CII=CIh CO■ClhCH・CIl■ CO■Cll■CECH CO■CH.C三CH CO■C6HS CO■C b It s CO■CH2C.iS CO.CII■C611, 011 0H QC}I. OCR. OC2Hs OCzHs OCH (Cl:l) z OCH (CH a) z C113 CH. C11, CI. Clh C1{3 C113 C11, CI13 CIl. CH2 C11, R1。NllCOCl+3 NIICO■C113 NIICOZCIh NIISO■CH3 N II S O. C.L. NHSO■CZHS NHSO C 2 11 5 CO■■ CO■II CO2 (JI3 CO■CL COzCzlls COzCzlls CO2Cll (CH3)z CO■Cll(C}+3)2 ? I.G. CO■ClI■CII=CIh CO■ClhCH・CIl■ CO■Cll■CECH CO■CH. C3CH CO■C6HS CO ■ C b It s CO■CH2C. iS C.O. CII■C611, 011 0H QC}I. OCR. OC2Hs OCzHs OCH (Cl:l)z OCH (CH a) z C113 CH. C11, C.I. Clh C1{3 C113 C11, CI13 CIl. CH2 C11, R1.
?CR2CH=CII■ OCHzCH−CHz OCH.C三Cll ocuzc=cu OCII(CI+3)C OCH(Cfh)C Sl1 SH SCI1. SCII1 SC2115 SCzHs CI+ C}I Clh R1。? CR2CH=CII■ OCHzCH-CHz OCH. C3Cll ocuzc=cu OCII(CI+3)C OCH(Cfh)C Sl1 S.H. SCI1. SCII1 SC2115 SCzHs CI+ C}I Clh R1.
SCII(CIl:l) z ?CII■CII=CH2 SCII■CIl=CH2 sco2c三Cl1 SCIhC =CI+ SCII(Cll:l)C三Cll SCH(Cll:+)CECII OCI12CO■11 0C11■CO■H OCH2CO■Clh OCH,CO■Clh OCH2C02C2H, ?,。SCII (CIl:l)z ? CII■CII=CH2 SCII■CIl=CH2 sco2c3Cl1 SCIhC = CI+ SCII (Cll:l)C3Cll SCH(Cll:+)CECII OCI12CO■11 0C11■CO■H OCH2CO■Clh OCH,CO■Clh OCH2C02C2H, ? ,.
OC11■CO■C 2 II 5
OC11■CO■CH(CL)z
QC}12cO■CH(CH3)2
?C11。CO■ClI■CIl・CIl■OCH2C
O2CII■Cll・CIl■O011■C02ClI
■C−FCIIOCHzCOzCH■CヨCll
OClhCO■C . It %
QC}12co■C . I+ ,
OCI−12CO■CH2C6H5
0Cll2COZCHZC6H5
0CH(CIl:l)CO21−1
0113
CI+3
?C11(CI13)CO■11
0C11(CI+3)CO2CH:1
0CII (C}l :l)CO■C1130CII
(CH3)CO■C.II,OCII (CI{3)C
O2C21150CI(C11z)Co■Cl(CI+
3)20CI{ (CHz) co■CH(Cllz)
zCff
Cl
Cl
Cl
?CII (CHI)COz−(IIIIOCII (
CH3)CO■−C
OCH(CH3)COZ−0
0CI (CH3)CO■−O
0
S
0
S
?CII (CI+3) CO2CIl2CH=CI+
20CII(CHz)CO■CH■Cll−CH,OC
H (CI+3)Co■Cll■C三CllOCH (
C41 3)CO■CII2C三CHCH.
?,。OC11■CO■C 2 II 5 OC11■CO■CH(CL)z QC}12cO■CH(CH3)2 ? C11. CO■ClI■CIl・CIl■OCH2C
O2CII■Cll・CIl■O011■C02ClI
■C-FCIIOCHzCOzCH■CyoCll OClhCO■C . It % QC}12co■C. I+, OCI-12CO■CH2C6H5 0Cll2COZCHZC6H5 0CH (CIl:l)CO21-1 0113 CI+3? C11(CI13)CO■11 0C11(CI+3)CO2CH:1 0CII (C}l :l)CO■C1130CII
(CH3)CO■C. II, OCII (CI{3)C
O2C21150CI(C11z)Co■Cl(CI+
3) 20CI { (CHz) co■CH (Cllz)
zCff Cl Cl Cl ? CII (CHI) COz-(IIIOCII (
CH3)CO■-C OCH(CH3)COZ-0 0CI (CH3)CO■-O 0 S 0 S ? CII (CI+3) CO2CIl2CH=CI+
20CII (CHz) CO■CH■Cll-CH,OC
H (CI+3)Co■Cll■C3CllOCH (
C41 3) CO■CII2C3CHCH. ? ,.
OCII (CH z)Co■C b II sOCH
(CI+3)Co■CHZC611SOCII (C
H3)COZCII■C&++SSCII■CO2H
SCII■CO■11
SC02CO■C113
SCII■CO■C113
SCII■CO2C2H,
SCII。COzCzlls
SC82CO■Cll (CIl:]) 25CII■
COZCII(CH3) 2?C}IzCOzCII■
CH二Cll■0
?IG
SCII■CO■ClI■C II = C II■S
CII2CO2CH2C=CII
SCII■COZC}+2c’EclISCHzCOz
CJs
SCII■CO■C . II ,
SCH 2CO■CH2C.IIS
SCII■CO2CH■C6HS
SCII(CI+3)CO2H
SCtl (Cll 3)CO■1{
SCH(CH3)Co■C113
SCII (CH :l)CO■C11,SCII (
Cll 3) CO■C 2It ,SCII (Cl
l :l) Co■C 2II ,SCII (CI1
3) CO■Cll (Cll 3) 25CH(C
th)Co■CH(Clh)2R,
R
X
?C11(C113)COzCHzCII・CIl■S
CII (CH :l)CO■Cll■CH=CIhS
C11(CI+3)COZCHZC三CIlSC11(
CI13)CO2CH2CECHSCH (CI+3)
Co■C . II ,SC11(CI1:l)COZ
C&+15SCII (CH 3)Co■CH2C6H
SSCH (CI1 ,)Co■ClI■C.H511
H
NHSO■CZl15
NHSOzCztls
CO2C211S
CO■C 2It ,
CH.
?1。OCII (CH z)Co■C b II sOCH
(CI+3)Co■CHZC611SOCII (C
H3) COZCII■C&++SSCII■CO2H SCII■CO■11 SC02CO■C113 SCII■CO■C113 SCII■CO2C2H, SCII. COzCzlls SC82CO■Cll (CIl:]) 25CII■
COZCII (CH3) 2? C}IzCOzCII■
CH2Cll■0? IG SCII■CO■ClI■C II = C II■S
CII2CO2CH2C=CII SCII■COZC}+2c'EclISCHzCOz
CJs SCII■CO■C. II, SCH2CO■CH2C. IIS SCII CO2CH C6HS SCII (CI+3) CO2H SCtl (Cll 3) CO ■ 1 { SCH (CH3) Co ■ C113 SCII (CH :l) CO ■ C11, SCII (
Cll 3) CO■C 2It ,SCII (Cl
l :l) Co■C 2II ,SCII (CI1
3) CO■Cll (Cll 3) 25CH (C
th)Co■CH(Clh)2R, RX? C11 (C113) COzCHzCII・CIl■S
CII (CH:l)CO■Cll■CH=CIhS
C11(CI+3)COZCHZC三CIlSC11(
CI13) CO2CH2CECHSCH (CI+3)
Co■C. II, SC11 (CI1:l) COZ
C&+15SCII (CH 3)Co■CH2C6H
SSCH (CI1,)Co■ClI■C. H511 H NHSO■CZl15 NHSOzCztls CO2C211S CO■C 2It, CH. ? 1.
OCII (Cll i) !
0CII (CIip) z
OCH ZC三CI1
OCII■CECH
OCR (CIl ff) C E CllOCH (
CH 3)C E CH
SCII (Cll 3) 2
SCH(CHz)z
SCII■CECI+
scnzc三CH
SCII (CI+ 3) C 三CHSCH(CI+
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OC11■Co,Clh
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NIISO■C z I+ 5
NIISO■C 2I+ 5
CO■C2H5
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OCH (Cll :l) 2
0CII (Cll 3) 2
0C■zcECll
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OCI! (CIl :t) C
C11,
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?,。OCII (Cll i)! 0CII (CIip) z OCH ZC3CI1 OCII■CECH OCR (CIl ff) C E CllOCH (
CH 3) C E CH SCII (Cll 3) 2 SCH (CHz)z SCII■CECI+ scnzc3CH SCII (CI+ 3) C 3CHSCH (CI+
3) CmiCH OC11■Co, Clh OC] 1■CO■C11, SCLC (hCL C113 C■, RIG ?CII■CO■C113 ?1 CO■C.H, ■ l1 11 NIISO■C z I+ 5 NIISO ■C 2I+ 5 CO■C2H5 CO■C 2 II 5 OCH (Cll :l) 2 0CII (Cll 3) 2 0C■zcECll OC11■C3CH OCI! (CIl :t) C C11, C■, ?,.
OCII(CI+3)C SCH(CIl:l)2 SCII (Cll :l) z SCH2C三CH SCII 2C E Cll SCH(CI+3)C SCtl(Ctl+)C OCH2CO■CH3 0CHZCO2Cl+:1 CI+ CI+ CH SGHzCOzClh ?CII■CO■C113 ?,。OCII(CI+3)C SCH(CIl:l)2 SCII (Cll:l)z SCH2C3CH SCII 2C E Cll SCH(CI+3)C SCtl(Ctl+)C OCH2CO■CH3 0CHZCO2Cl+:1 CI+ CI+ CH SGHzCOzClh ? CII CO C113 ? ,.
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SCH (Cll 3)C =Cll
SCH (CI+ 2) C ml: CHOC11■
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h)z
SCII (Cll i) 2
SCH2CECH
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?IG
SCII(CIl:l)C
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?1。11 11 CO■C. I+ 5 11 ■ II N If S 0 2 C 2 II SNllSOz
CJs CO■C. }I, COzCzlls OCII (CIl-x> 2 0CH(Cllz)z OCII■CEECI1 OCH ,c E Cl1 OCII(CHz)C3CH OCR(CH+)CECH SC■(CHz)z C1[3 ?CI12C = Cll SCH ■C3CI+ SCH (Cll 3)C = Cll SCH (CI+ 2) C ml: CHOC11■
C.O. CH3 0CHzC(hcHa ?CII■CO■CH3 SCHzCOzCHz ■ ?O■C113 ?IG 11 ■ ]I NHSO■C . I+ , NHSO■C ! II 5 CO■C2HS C(hcztls OCII (Cll :l) t OCII(Clh )z OCR2CECI1 OCR2CECI+ OCH(CIiff) C3CI+ OCII (Cll :l) C3(JISCII(Cl
h)z SCII (Cll i) 2 SCH2CECH SC}l. c: Cl+ C11, ? IG SCII (CIl:l)C OC11■CO■CD. OCH2CO■Cll. CI+? 'C II■C02Clh? CII■CO■CR, ? 1.
CO■Cz It s CO2C211S OCR(CH:l)2 0CII (CHz) z OCH 2C−CII O011■C:CH OCH(CfL+)C OCII (CIl :l)C SCtl (Cll 3) 2 5CH (Cll :l) 2 SCIIzcECH SCII■CECII SCII(CH3)C SCII(CI13)C OC{1■CO■C113 0CH2CO2Cll3 CI+ CI1 CI+ Cll C11, ■ F ?O■ ?CII■C02Clh 0 Clh ■ F ?O■ ?CII■C02Clh S 11 H F ?O■ 11 0 11 F F ?O■ 11 0 Cll. F F NO2 ■ 0 (以下、 余白) 第4 1表 RM7 Rl7 ?1 1I 11 C113 C113 C 2I+ , C . I1 , CH 2CH ZCI1 3 CHzGHzCtl3 CH(CH3)2 Cll (Cllz) z CII■C I1 = C I■ ?l? CII■C II = C II■ CII■C=CIl CH2C=:CII CIl■CJs ?}I.CN CH.CN CI12CONH2 CH2CONI+■ CH2011 CI+20H CII.i CH■ Ci ■ ■ H C113 CH3 C113 CII3 C}13 C113 C113 CU3 CH3 C113 CH3 C113 Ctl3 ?113 Cl3 C.I{5 C2H5 CLCII■CIl, CHzCII■CH, Cl(CHa)z Cll (CI13) 2 Cll■CIl:CIl2 CflzCH=CHz CH 2CミCII CIl■C三CI CII2C6}1s CH2CN CHi CH. CH, C113 Cll3 C113 CH, II3 C{13 CL 6113 CH. CH3 CH, ?Il■CONII■ CIl,CONI{2 Cll■OH Cl1■011 CH2CI CH2 (J Cl{2CミCII CII■C=CI1 11 11 CzHs CzHs C}I2C三CH ■ ■ CH3 C113 C11, C113 C113 F C z If s F C211, F CH2CミCl−1 H ■ C z tl s C 2 tl s CIl2C三CH lI H C2HS R6 R7 R. Rl? (Jlff NO2 F cugc=c++ (以下、 余白) X O 第4 2表 R ?1■ 11 !I C ,!I+ 5 C 2I+ 5 CH2CECIl ■ 11 C2 H s C211, CF. CH3 RI7 CH.CミCI1 ? 11 11 C}1, C113 C2H, C Z If S CIl■Cll2Clh ClI■CIl.CH. CH(CH,l)2 Cll (Cll 3) 2 CHzCH=CHz Cll■CI=CII■ CH,CミCIl ?lt Cll■C三Cll CIl■C6HS Cll■C6HS ?ll2CN CIl■CN CII■CONI+2 ClI■CONll2 CH2011 CI−1208 CIl■01 CIl■01 II II C2115 C2H, C11, Rl7 ClhC三CI+ ?1 11 C 2II S CJs CII■C=CI+ ■ ■ Czlls C.HS CH2C=CI CI, RI7 CH 2C三Cl1 ]{ 1i CzHs C2115 CH,C−:CH CH2C三CH ?l? C z It s CIl■CIl■Cl3 Cll■CHzCIIz Ctl (Cll:+) z Cll (CI+3) z Cll■C}l=cL CHgCH−CHz cozc=cu CH,CミCH Cll■C.II, CHZC6HS ?Il,CN CH2CN CIIZCONH2 CH,CONII■ ?I+■011 CI1■011 Cll,Cjl! CIl■ Cl 11 H C 2II S C 2II , Cl2C三CH CH.C:CH 11 II Czlls C.IIS cuzc三Cl1 CH3 CI+:10 (Jl ,10 CH:lO CII+0 Rl? ?II■C三CH ?1 H CzHs CzHs CIl■CiCH CH2CミCI 11 ■ C 2 It 5 C 2 I+ 5 CI130 CIIF20 CIIF20 CllFtO CIIP.O CHF20 CIIF,0 CFJO CF30 CF,O CF30 CF 3o C}I2C三Cl−1 ?1 11 CtI+5 CzH5 CH■C:ClI CII■CECII 11 11 C 2II 5 CzHs CH 2cミCH R2 R, R7 R. Rl? CF30 C113 ■ F CH2C三CH ClhCO C}I .CO Cll,IcO CH.CO Cll3Co CH.C0 ?1 11 C 211 S C2HS cnzc=c++ CII■C=CIl ?O■C 21+ S COzCzlls CO■C . 11 S CO■C 2II S ■ 11 C2H, C2HS R2 R6 R7 R8 Rl? X ?O■CzHs C113 H F ?ll■C−1:Cl1 S (以下、 余白) 第4 3表 ?1 I1 11 Cl+3 Cth C2H, Cdl5 CI12CII■611, ClI■Cll■011, CH(CH3)2 Cll (Cll 3) Z CH2CH=CH2 ?HzCIl=CII■ CH.CミCH ClI■C=CII CHZC&+1, ?}l.cN CHzCN CHzCONHz CHzCONHz CH20H CI+■011 CII■ C! CIl■ CI ■ 11 Cz II s 6113 Cll. CI. Cll. C113 CH, CH, CH. CI. Rl? ?.l1, Cll■C三CH CH■C三CH ? {I CJs C.Hs C}I2C:CH Cll■C三CH ■ } CtH, 1?. (Jl3 C{13 C11, C11, CH. C113 CH, C!13 C1{, C]13 RM? C ! II 5 CH.CミCH CH.CミCIl 11 H CJs C2H5 CHZC=CI1 11 ■ ■ CHI I?1, ?113 CH. C.HS C . I1 . CII■CIl■C11, CII■CIl■C]1, CIl (CI+4) Z Cll (CIlJ) I CH2CI=CII■ (JlzClbCHz CH.CミClI CIl■C三CI CH!C.Hs CHzC.H, CI.CN Rl? ?Il■CN CH2CONlI■ CI12CONll■ CI+■011 CH20H ClI■ CP CH2Cf (以下、 余白) 第4 4表 R. 11 CH. CI!3 C113 CHI Cll3 Cl. CIl. CHff CH. CH,1 Rl? 11 ■ 11 CH3 011, C . I+ , C.}Is CHzCHzCtl+ CH2CH2CH3 Ctl (CH 3) ! CH(CIl+)z R6 Cl, CH3 CI. 0113 CH, CI, C{13 C11, C11, C11, C113 C113 CH3 11 CH. ?I7 CIl!CIl=CIl■ CH■c=ctt CH.CミCH CH.C.H, CH2C6115 ?H2CN CIl■CN CH■CONtlz CH2CONI1■ CIl■OH CH2011 CII■ C! Cll■ Cffi ■ ]1 Rl? ?I CL C11, C 2II S C . I1 , CH■C82CI+3 CH2CII■C11, CH (Cl z) z Cll (Cll z) z CIIzCll=CHz CH2Cll・Cl2 CII■C=CU CII■C=:CH CII■C.H, CLC6l1s R6 C1{4 C113 C11, C113 C113 Clh Cll3 C113 C113 CH3 C113 C113 C1{3 C113 C1]3 Rl? ?Il■CN CIl■CN CII■CONH2 Cll■CONFl2 Clh011 C}120H CII2Cffi CII■ C! 11 11 C 2 II S C2H, CI12C三Cll CII■C=CI1 11 Rl? ■ C 2I1 , C 2II , CH2C:CII CIltC=CH ■ 11 C,H, C2H!, CH.CミCIl CH2C二Cl ■ C113 C1{3 C11, C113 C113 11 C z It s Czlls CH2C三Cl1 cnzc=c++ (以下、 余白) 第4 5表 ?l? 11 ■ lI CH3 C11, C,H, C . II S CIl■CllzCII1 CHiCHzC}l3 CI(CHs)z CI(CHs)z CHzCH=CHz ?l7 CH 2Cll = CII■ Cll ,C : CH CH.CECII CII■C . II 5 C II Z C b H s ?Il■CN CIl■CN CH2CONII■ CHzCONHz CI+■011 CI1■011 Cll■Cffi CII■C! ■ ■ II ?11, C11, C.H5 C,HS CIl■CI12CII3 CHzCHzClb Cll (Cll 3) Z Cll(CHz)z CIIzCll””CHz CHzCH=C}lx CH,C::Cll ClI■C三CH CHzCills Cll。C.l1, cozcN ?H.CN CHzCONHz CHzCONHz CI+■011 CI+■011 CH.Cjl! CIl■(J H H C 2 II 5 C2HS CH2C三Cll CIl■C:CI+ H H C!l{S czus ?II■CECI1 CIl.CE:CH ?1 11 CzHs C.Hs CII■C”:CI1 CtjtC三Cll ■ H C.Hs C.HS れ R7 R. RI’? X C11, NOt F ClhCECI1 0 CI, ?O■ F CH2CECH S (以下、 余白) 第4−6表 ■ ■ ■ C11, C6 CtHs CtH, C}IzClhCH2 CHtCHtCHs CH(CHi)t CH(CI.)寞 CH*CH=CHt ?H zcll = Cll ! CII■C−:ClI CI1■+,:Cll CHzCJs CHzChHs ?H.CN cozcN CHzCONHz CI,CONI+■ CHgOII CH,011 cozcl CIl.Cffi ■ 11 ■ ?−! CI. C11, C I II , CtHS CHzCIhCHz CH*CHzCHs Cll(Clls)z CH(CHs)z CIIzCII=CHx ClI■CII=CIZ ClbCミCH CHzC:CH CHzCills CHzCalls CI.CN ?Il■CN CHzCONIIg C}IzCONHz CI208 Cll■011 CII■CI CIl■CN H H C2115 C . I+ , CH2C−CII CII■C−:CII ■ ■ CJs CHZCミCI ClhCE:Cl1 ? H Cfl+5 C211, CII■C:CII CflzCミCH ]1 ■ C,H, CzH, CL NO, F CIhCECII 0 CL NO, F CH2C CI S (以下、 余白) 第5 1表 ? ■ CH3 C11, CtHs cz+ts CIIzGHzCL CHzCII■Clh CI(CHz)z CH(Clli)i CIl■CI=CH2 ?l? CII■Cll = CII■ CII■C=CI CII■C=CII CII■C6HS CIIzC6Hs ?}I2CN CIl■CN CII■CONlh CII■CONI+■ CH.011 CI!OH CH2Cj! CIIZCQ ■ 11 11 ?H, CI. C z It s CzHs CHzClbClls CflzCHzCHs CH(Cllz)z Cl(CJ)z CHzCIl=CHi CJCH=CHi CltC=CIl CI,C:CH Cll■C6115 CHzCJs CH2CN ?Il■CN CIZCONI1■ CII■CONI+■ CI−12011 CI+■011 CII■CI CIl2C/! H H C . II 5 C2HS CH.C:CH CII■C−1FCI1 ■ H C , I+ , ?l. C.II5 CIl■CミCH CIhCミCH ? H Cills C.HS CII■C CII■C CI+ Cll H H CzHs C 2II S CII3 ?O■ F Cll.CミCl+ 0 CH3 NO, F CI.CミCH S (以下、余白) 第5−2表 ?1 ■ CtHs CzHs Cl■CECH CH.C =CH ■ ■ C!HS Czlls CH!CミCI ?II■C:CH ? H H Cl+, CI. CtHs CJs CIl■CH.CI. CII■CI12CI+3 CIl(Cll.)z CH(CH3)z CH!CH=CH! CHzCll=CHz Cll,CECII CHzC三CH CIIzCJs CHzCJs ?tl.CN CH!CN CII■CONHz CJCONHz CI,OH Cll■OH CH!CI CI,CIl ■ 11 C t tl s CtH, Rl? Cll zC −E Cll Cll tc 三elf ? ■ C . II S C2HS CII■C−:CIl CII.CECII ? 11 czos CzHs CIl■Cl:Cl+ Lt cnzc CI1 ■ ■ CtHs C.H, CI.(,’CIl CH.C::CI冒 ?l? C ! II 5 CHtCHgCH3 CHzCHzCHs (Jl (Cllz) − Cll (CH :l) z CHZCI=CH2 Cll■CI = CIl * CH2C三CI ClhCEICH CIl■C b II s (jl.c.l+, ?Il,CN CIl,CN CIlzCONll■ ClI■CONIh CH,011 CH. CH. C11, CHi CH3 C11, CH3 CH, CL Clh Cll. CI3 CHs CH2 CH3 ?Il■Oil Cl,Cffi CI.Cf H 11 C 21( , CJs CI,C:ECII c++zc=c 目1 H ■ C.HS czus CH.CECH Cl1 2C E CH CIl,O CH30 ClhO Cll:lO CH.O CH30 C!{, CH3 CH. CH3 CHz CH. RI7 ?l ■ C,H5 C2HS CIl■C::CII CIl■C:ECII ?1 ■ C.H, C . II S CII■C−:CI+ CHZC三CH CHF.O CIIP.O CHF.O C}lF.O CIIF20 CHF20 CF30 CF.O CF,O CF30 CP30 CF30 Rl? H ■ C . 11 , C.H, cuzcミCll CI .C三CIl 11 ■ C . H , C . I1 , CHzC:Cll CH2CECll R. R6 R? R8 R+? CH.CO ClhCO Cll3CO CH2CO Cll3CO Cl13Co C113 CH. C113 C113 CH. C11, 11 11 C 2I1 , C2}15 CH2C−ECH CH.C三C}l ?(hc.Hs CO2C2115 C(hczlls COzCzlls CO■C 2 II S C113 Cl. CH. CH3 C11, 11 H C2HS CzHs CH2CECH R2 R. R7 R8 R−7 X (以下、 余白) 第5 3表 ?1 ■ ■ CII+ CL C.l+, C 2 I1 , CLCI12CI13 CI!CIl■C11, CH(CHJz 1(Clli)z Cl{.CFI=CI1! ??1, CtlzCII =CIh Cll.CECH CH.CEClI CIl■CthHs CH.C.H, ?I.CN Cll■CN CH.CONHffi CHzCONL CH.011 CH20H Cll.C1 cuzc1!. H ■ C . II , Rl’I C 2I1 , CIl2C三Cll ClhCミCH 11 H C.H, C2H, CI.C CH.C CH CI ■ U C.H, Rl? ct+xc CI+ CH2G CH ■ H CtHs C,H, CH2C−;Cl! CI.CECI1 ?+7 C .+1 , C z It s CHzCll■Cll. CHiCHtCHs CH(Clll)z CH(Clls)z CHiCll=CHt Cll!CIl=CI! CII.CECll CH.C三CH ClhCJls CHzCthHs ClltCN CH!CN CHzCONHz CH*CONH* ?Hz011 Cll■OH ClI■Cl cthcf (以下、 余白) 第5−4表 ■ H ■ CH, C11, CJs CJs CHzGHzCHi CIl!ClオCH, CH(CI.)! CIl(Clh)z CH*CH=CHz RI’? CHzCII=CIh CH.C三CIl CI .C : CIl CI.C.H, CH2C.H, ?lhCN CI.CN CII■CONI+■ CII■CONI+■ CI,011 CI.OH CIl■CIl CIl■Cf } H H ?−7 C11, CH3 C . I1 , CJs CH2Cll■CHs Cll.CIl■CH3 Cll (Cll z) z CH(CH3h Cll■CII=C}l. ClI■CIl=CII■ CH.C三CI CIl■CECH Cll■Cills CH■C.H, CHtCN ?Il■CN ClI■CONH! ClbCONlh Clh011 CIl■0■ CIl■CI!. CH2CI! 11 11 C z It s C . II , CI.C三CH CH.C:CIl ■ ■ C2H5 ?l’7 Cz If s CO.C Cll■C CI CI+ ? H CJs C.H, CI.C CII■C CI1 CI H ■ CIHS C.H, P, R7 R@ Rat X CH3 NO2 F CI.C CI1 0 CH3 ?O■ F CH2CミCI S (以下、 余白) 第5 5表 ■ 11 H CH. C11, C z It s C.H, CHzCHzCHi CHzcnzcnl CH(CH3)2 Cll((Jls)z CH.CH=CI. ?ift CIl zcll = Cll■ Cll■C−CH Cll■CECII CH■Chis Cll■C& 11 5 ?Il■CN ClhCN ClI■CONII■ ClI■CON82 Cl−1,011 CH20H Cll■Cl CIl.Cffi ■ H ■ ?l? CM. CI. C,HS C.H, CH2Cl12CH:I CIl■CI!CI13 CI(Cll3:h CH(CH3)2 CHzCIl=CHz CHzCH−CHz CH!CECII CH!C:CH CH,C6115 CHzCills ?Il■CN ?+? CI12CN CIl。CONH2 CII■CONI12 CH.011 cuton CH2CI CIl■C1 ■ 11 C.HS C t II 5 CH,C:CI1 CH2C三Cl+ ■ ■ C.I+, 1 ?l? Czlls CIIzC Cll■C CH CI1 ?1 11 CzHs C2L Cll2C Cll■C CI+ CH 11 H CJs C2H5 C11, ?O■ F ?Il■CIECI+ 0 CHz NO。 CO ■ CZ IT S CO2C211S OCR (CH: L) 2 0CII (CHZ) Z OCH 2CH 2CH 2CH 2CH 2CH 2CH 2CH (CFL +) C OCII (CIL: L) C SCTL (CLL 3) 25ch (CLL: L: L: L: L: L: L ) 2 SCIIzcECH SCII■CECII SCII(CH3)C SCII(CI13)C OC{1CO■C113 0CH2CO2Cll3 CI+ CI1 CI+ Cll C11,F? O■? CII■C02Clh 0 ClhF? O■? CII■C02Clh S 11 HF? O■ 11 0 11 F F? O ■ 11 0 Cll. F F NO20 (hereinafter referred to as blank space) Table 4 1 RM7 Rl7 ? 1 1I 11 C113 C113 C 2I+ , C . I1, CH 2CH ZCI1 3 CHzGHzCtl3 CH(CH3)2 Cll (Cllz) z CII■C I1 = C I■? l? CII■C II = C IICII■C=CIl CH2C=:CII CIl■CJs? }I. CN CH. CN CI12CONH2 CH2CONI+CH2011 CI+20H CII. i CH■ CiH C113 CH3 C113 CII3 C}13 C113 C113 CU3 CH3 C113 CH3 C113 Ctl3? 113 Cl3 C. 1s CH2CN CHi CH. CH, C113 Cll3 C113 CH, II3 C{13 CL 6113 CH. CH3 CH, ? Il■CONIICIl,CONI{2 CllOH Cl1011 CH2CI CH2 (J Cl{2CmiCII CII■C=CI1 11 11 CzHs CzHs C}I2C3CHCH3 C113 C11, C113 C113 F C z If s F C211, F CH2CmiCl- 1 HC z tl s C 2 tl s CIl2C3CH lI H C2HS R6 R7 R.Rl? (Jlff NO2 F cugc=c++ (hereinafter, margin) X O 4th 2 Table R ?111 !I C ,!I+ 5 C 2I+ 5 CH2CECIl11 C2 H s C211, CF.CH3 RI7 CH.CmiCI1 ?11 11 C}1, C113 C2H, C Z If S CIl■Cll2Clh ClI■CIl.CH.CH(CH,l)2 Cll (Cll. 3) 2 CHzCH=CHz CllCI=CIICH, CmiCIl ?ltCll■C3Cll CIl■C6HS Cll■C6HS ?ll2CNCIl■CN CII■CONI+2 ClI■CONll2 CH2011 CI-1208 CIl 01 CIl01 II II C2115 C2H, C11, Rl7 ClhC 3CI+ ?1 11 C 2II S CJs CII■C=CI+Czlls C.HS CH2C=CI CI, RI7 CH 2C3Cl1 ]{ 1i CzHs C2115 CH,C-:CH CH2C3CH ?l?C z It sCIl■ CIl■Cl3 Cll■CHzCIIz Ctl (Cll:+) z Cll (CI+3) z Cll■C}l=cL CHgCH-CHz cozc=cu CH,CmiCH Cll■C.II, CHZC6HS ?Il,C N CH2CN CIIZCONH2 CH ,CONII?I+011 CI1011 Cll,Cjl!CIlCl 11 H C 2II S C 2II , Cl2C3CH CH.C:CH 11 II Czlls C.IIS cuzc3Cl1 CH3 CI+:10 (Jl , 10 CH:lO CII+0 Rl?? II■C3CH ?1 H CzHs CzHs CIl■CiCH CH2CmiCI 11C 2 It 5 C 2 I+ 5 CI130 CIIF20 CIIF20 CllFtO CIIP. O CHF20 CIIF,0 CFJO CF30 CF,O CF30 CF 3o C}I2C3Cl-1? 1 11 CtI+5 CzH5 CH■C:ClI CII■CECII 11 11 C 2II 5 CzHs CH 2cmiCH R2 R, R7 R. Rl? CF30 C113F CH2C3CH ClhCO C}I. CO Cll, IcO CH. CO Cll3Co CH. C0? 1 11 C 211 S C2HS cnzc=c++ CII■C=CIl? O■C 21+ S COzCzlls CO■C . 11 S CO■C 2II S11 C2H, C2HS R2 R6 R7 R8 Rl? X? O■CzHs C113 HF? ll■C-1:Cl1S (hereinafter referred to as margin) Table 4 3? 1 I1 11 Cl+3 Cth C2H, Cdl5 CI12CII611, ClI■Cll011, CH(CH3)2 Cll (Cll 3) Z CH2CH=CH2? HzCIl=CIICH. CmiCH ClI■C=CII CHZC&+1, ? }l. cN CHzCN CHzCONHz CHzCONHz CH20H CI+011 CIIC! CIlCI11 Cz II s 6113 Cll. C.I. Cll. C113 CH, CH, CH. C.I. Rl? ? .. l1, Cll■C3CH CH■C3CH? {I CJs C. Hs C}I2C:CH Cll■C3CH} CtH, 1? .. (Jl3 C{13 C11, C11, CH.C113 CH, C!13 C1{, C]13 RM?C !II 5 CH.CmiCH CH.CmiCIl 11 H CJs C2H5 CHZC=CI1 11CHI I?1 , ?113 CH.C.HS C .I1 .CII■CIl■C11, CII■CIl■C]1, CIl (CI+4) Z Cll (CIlJ) I CH2CI=CII(JlzClbCHz CH.CmiClI CIl■C3 CI CH!C.Hs CHzC.H, CI.CN Rl? ?Il■CN CH2CONlI■ CI12CONllICI+011 CH20H ClI■ CP CH2Cf (hereinafter, margin) 4 4 Table R.11 CH.CI!3 C113 CHI Cll 3 Cl.CIl .CHff CH.CH,1 Rl?1111 CH3 011, C .I+ , C.}Is CHzCHzCtl+ CH2CH2CH3 Ctl (CH 3) !CH(CIl+)z R6 Cl, CH3 CI.0113 CH, CI, C{13 C11, C11, C11, C113 C113 CH3 11 CH. ?I7 CIl!CIl=CIlCH■c=ctt CH.CmiCH CH.C.H, CH2C6115 ?H2CN CIl■CN CH■CONtlz CH2CONI1CIlOH CH 2011 CIIC! CllCffi] 1 Rl? ?I CL C11, C 2II S C .I1, CH■C82CI+3 CH2CII■C11, CH (Cl z) z Cll (Cll z) z CIIzCll=CHz CH2Cll・Cl2 CII■C=CU CII ■C=:CH CII■ C.H, CLC6l1s R6 C1{4 C113 C11, C113 C113 Clh Cll3 C113 C113 CH3 C113 C113 C1{3 C113 C1]3 Rl? ?Il■CN Cll■CN CII■CONH2 Cl■CONFl2 Clh011 C}120H CII2Cffi CIIC! 11 11 C 2 II S C2H, CI12C3Cll CII■C=CI1 11 Rl?C 2I1 , C 2II , CH2C:CII CIltC=CH11 C,H, C2H!, CH.CmiCIl CH2C2ClC113 C1{3 C11 , C113 C113 11 C z It s Czlls CH2C3Cl1 cnzc=c++ (hereinafter, margin) Table 4 5 ? l? 11lI CH3 C11, C, H, C . II S CIl■CllzCII1 CHiCHzC}l3 CI(CHs)z CI(CHs)z CHzCH=CHz ? 17CH 2Cll = CIICll, C: CH CH. CECII CII■C. II 5 C II Z C b H s? Il■CN CIl■CN CH2CONIICHzCONHz CI+011 CI1011 Cll■Cffi CII■C! II? 11, C11, C. H5 C,HS CIl■CI12CII3 CHzCHzClb Cll (Cll 3) Z Cll(CHz)z CIIzCll""CHz CHzCH=C}lx CH,C::Cll ClI■C3CH CHzC ills Cll. C. l1, cozcN? H. CN CHzCONHz CHzCONHz CI+011 CI+011 CH. Cjl! CIl(J H H C 2 II 5 C2HS CH2C3Cll CIl■C:CI+ H H C!l{S czus ?II■CECI1 CIl.CE:CH ?1 11 CzHs C.Hs CII■C":CI1 CtjtC三CllH C.Hs C.HS Re R7 R.RI'? Hs CH (CHi)t CH(CI.)寞 CH*CH=CHt ?H zcll = Cll !CII■C-:ClI CI1+,:Cll CHzCJs CHzChHs ?H.CN cozcN CHzCONHz CI, CONI+CH gOII CH,011 cozcl CIl.Cffi11? -!CI.C11, C I II, CtHS CHzCIhCHz CH*CHzCHs Cll(Clls)z CH(CHs)z CIIzCII=CHx ClI■CII=CIZ ClbCmiCH CHzC:CH CH zCills CHzCalls CI.CN ?Il■CN CHzCONIIg C }IzCONHz CI208 Cll011 CII■CI CIl■CN H H C2115 C .I+ , CH2C-CII CII■C-:CIICJs CHZCmiCI ClhCE:Cl1 ?H Cfl+5 C211, CII ■C: CII CflzCmiCH]1C,H, CzH, CL NO, F CIhCECII 0 CL NO, F CH2C CI S (hereinafter, margin) Table 5 1 ?CH3 C11, CtHs cz+ts CIIzGHzCL CHzCII■Clh CI(CHz)z CH(Clli)i CIl■CI=CH2? l?CII■Cll = CIICII■C=CI CII■C=CII CII■C6HS CIIzC6Hs ?}I2CN CIl■CN CII■CONlh CII■CONI+CH.011 CI!OH CH2Cj!CIIZCQ11 11 ?H, CI.C z It s CzHs CHzClbClls CflzCHzCHs CH(Cllz)z Cl(CJ)z CHzCIl=CHi CJCH=CHi CltC=CIl CI,C:CH Cll■C6115 ChzCJs CH2C N? Il■CN CIZCONI1CII■CONI+CI-12011 CI+011 CII■CI CIl2C/! HHC. II 5 C2HS CH. C:CH CII■C-1FCI1H C, I+, ? l. C. II5 CIl■CmiCH CIhCmiCH? H Cells C. HS CII■C CII■C CI+ Cll H H CzHs C 2II S CII3? O ■ F Cll. Cmi Cl+ 0 CH3 NO, F CI. C Mi CH S (hereinafter referred to as blank space) Table 5-2? 1CtHs CzHs Cl■CECH CH. C=CHC! HS Czlls CH! CmiCI? II■C:CH? H H Cl+, CI. CtHs CJs CIl■CH. C.I. CII■CI12CI+3 CIl(Cll.)z CH(CH3)z CH! CH=CH! CHzCll=CHz Cll, CECII CHzC3CH CIIzCJs CHzCJs ? tl. CNCH! CN CII■CONHz CJCONHz CI,OH CllOH CH! CI CI, CIl11 C t tl s CtH, Rl? Cll zC -E Cll Cll tc three elf? C. II S C2HS CII■C-: CIl CII. CEC II? 11 czos CzHs CIl■Cl:Cl+ Lt cnzc CI1CtHs C. H, CI. (,'CIl CH.C::CI effect ?l?C !II 5 CHtCHgCH3 CHzCHzCHs (Jl (Cllz) - Cll (CH :l) z CHZCI=CH2 CllCI = CIl * CH2C3CI ClhCEICH CIl ■ C b II s (jl.c.l+, ?Il,CN CIl,CN CIlzCONlllClI■CONIh CH,011 CH.CH.C11, CHi CH3 C11, CH3 CH, CL Clh Cll.CI3 CHs CH2 CH3 ?IlOil Cl , Cffi CI.Cf H 11 C 21( , CJs CI,C:ECII c++zc=c Eye 1 HC.HS czus CH.CECH Cl1 2C E CH CIl,O CH30 ClhO Cl:lO CH.O CH30 C!{, CH3 CH.CH3 CHz CH. RI7 ?lC,H5 C2HS CIl■C::CII CIl■C:ECII ?1C.H, C.II S CII■C-:CI+ CHZC3CH CHF.O CIIP.O CHF.O C}lF.O CIIF20 CHF20 CF30 CF.O CF,O CF30 CP30 CF30 Rl?HC .11 , C.H, cuzcmiCll CI .C3CIl 11C .H , C .I1 , CHzC:Cll CH2CECll R.R6 R?R8 R+? CH. CO ClhCO Cl13CO CH2CO Cl13CO Cl13Co C113 CH. C113 C113 CH. C11, 11 11 C 2I1 , C2}15 CH2C-ECH CH. C3C}l? (hc.Hs CO2C2115 C(hczlls COzCzlls CO■C 2 II S C113 Cl.CH.CH3 C11, 11 H C2HS CzHs CH2CECH R2 R.R7 R8 R-7 Table 3 ?1CII+ CL C .l+, C 2 I1, CLCI12CI13 CI!CIl■C11, CH(CHJz 1(Clli)z Cl{.CFI=CI1! ??1, CtlzCII =CIh Cll.CECH CH.CEClI CIl■CthHs C.H.C.H. , ?I.CN Cll■CN CH.CONHffi CHzCONL CH.011 CH20H Cll.C1 cuzc1!.HC .II , Rl'I C 2I1 , CIl2C3Cll ClhCmiCH 11 H C.H, C2H, C I.C.H. .C CH CIU C.H, Rl?ct+xc CI+ CH2G CHH CtHs C,H, CH2C-;Cl!CI.CECI1 ?+7 C .+1 , C z It s CHzCll■Cll.CHiCHtCHs CH (Cllll) z CH(Clls )z CHiCll=CHt Cll!CIl=CI!CII.CECll CH.C3CH ClhCJls CHzCthHs ClltCN CH!CN CHzCONHz CH*CONH* ?Hz011 CllOH ClI■Cl cthcf (hereinafter referred to as margin) Table 5-4 HCH, C11 , CJs CJs CHzGHzCHi CIl!CloCH, CH(CI.)!CIl(Clh)z CH*CH=CHz RI'?ChzCII=CIh CH.C3CIl CI .C: CIl CI.C.H, CH2C. H, ?lhCN CI.CN CII■CONI+CII■CONI+CI,011 CI.OH CIl■CIl CIl■Cf } H H ?-7 C11, CH3 C .I1 , CJs CH2Cll■CHs Cll.CIl■CH3 Cll ( Cll z) z CH(CH3h CllCII=C}l.ClI■CIl=CIICH.C3CI CIl■CECH CllCills CH■C.H, CHtCN ?Il■CN ClI■CONH!ClbCONlh Clh011 CIl0CIl■CI!.C H2CI!11 11 C z It s C. II, CI. C3CH CH. C:CIIC2H5? l’7 Cz If s CO. C Cll■C CI CI+? H CJs C. H, CI. C CII■C CI1 CI HCIHS C. H, P, R7 R@ Rat X CH3 NO2 F CI. C CI1 0 CH3? O ■ F CH2Cmi CI S (hereinafter referred to as margin) 5th Table 11 H CH. C11, C z It s C. H, CHzCHzCHi CHzcnzcnl CH(CH3)2 Cll((Jls)z CH.CH=CI. ?ift CIl zcll = CllCll■C-CH Cll■CECII CH■Chis Cll■C& 11 5 ?Il■CN ClhCN ClI■CONIIClI ■ CON82 CL -1, 011 CH20H CLL ■ CL CIL.CFFIH? L? L? L? CM.C, HS C.H, CH2CL12ch: ICIL ■ CI! CI13 CI (CLL3: HCH (CH3) CHZ CHZCH -CHz CH!CECII CH!C:CH CH,C6115 CHzCills ?Il■CN ?+?CI12CN CIl.CONH2 CII■CONI12 CH.011 cuton CH2CI CIl■C111 C.HS C t II 5 CH, C: CI1 CH2C3 Cl+C.I+, 1 ?l?Czlls CIIzC Cll■C CH CI1 ?1 11 CzHs C2L Cll2C Cll■C CI+ CH 11 H CJs C2H5 C11, ?O■ F ?Il■CIECI+ 0 CH z NO.
F
CI.CECH
S
(以下、
余白)
第5
6表
?1
■
H
C}1,
C113
Czlls
C z If s
CHzCIIzCH3
CI,CIl■C]1,
CI(CHz)z
CI (Cll s) z
CH.CH=CI1■
?l,
Cll .CIl = CII■
CIl■C:CII
CII■CECII
CH.C.H,
CII■C , I+ ,
?}l.cN
CIl.CN
CllZCONll2
CIl■CONHz
CH2011
CI{.OH
CH.CI!.
CH2(1!
■
11
?l?
■
C11,
CI.
C2HS
C.H,
CII■CIl■C11,
CII■CIl■C11,
CH(CHs)z
Cll(CII3)z
CH zcH = Cll■
CHzCll=CHz
CH.C三CI
CII■C:CH
CHzC6115
CHzCaHs
CI.CN
?’l1?
C}I,CN
CH2CONll■
CIIzCONHz
cozou
CIl■Oil
CH.Cffi
CH.Cff
H
■
C.H%
C.H,
CII■C:CH
CH.C:CH
■
■
C.H,
R+?
C.l1,
CH!C三CH
cozc=co
11
H
C!us
C.H,
CHffiC:CI
CI.CECH
11
11
CtHs
C1l{S
C113
NO.
F
C}l ,c
Cl+
0
C!1,
?O■
F
CH2C
CH
S
(以下、
余白)
本発明化合物を除草剤として施用するにあたっては、一
IIには適当な担体、例えばクレー、タルク、ヘントナ
イト、珪藻上、ホワイトカーボン等の固体担体あるいは
水、アルコール類(イソプロバノール、ブタノール、ヘ
ンジルアルコール、フルフリルアルコール等)、芳香族
炭化水素類(トルエン、キシレン等)、エーテル類(ア
ニソール等)、ケトン頻(シクロヘキサノン、イソホロ
ン等)、エステル類(酢酸ブチル等)、酸アミド類(N
−メチルピロリドン等)またはハロゲン化炭化水素類(
クロルベンゼン等)などの液体担体と混用して適用する
ことができ、所望により界面活性剤、乳化剤、分散剤、
浸透剤、展着剤、増粘剤、凍結防止剤、固結防止剤、安
定剤などを添加し、液剤、乳剤、永和剤、ドライフロア
プル剤、フロアブル剤、粉剤、粒剤等任意の剤型にて実
用に供することができる。FCI. CECH S (hereinafter referred to as margin) Table 5 6? 1 ■ H C}1, C113 Czlls C z If s CHzCIIzCH3 CI, CIl■C]1, CI (CHz)z CI (Cll s) z CH. CH=CI1■? l, Cll. CIl = CII ■ CIl ■ C: CII CII ■ CECII CH. C. H, CII■C, I+, ? }l. cN CIl. CN CllZCONll2 CIl■CONHz CH2011 CI{. OH CH. CI! .. CH2(1! ■ 11 ?l? ■ C11, CI. C2HS C.H, CII ■ CIl ■ C11, CII ■ CIl ■ C11, CH (CHs)z Cll (CII3)z CH zcH = Cll■ CHzCll=CHz CH .C3CI CII■C:CH CHzC6115 CHzCaHs CI.CN ?'l1? C}I,CN CH2CONll■ CIIzCONHz cozou CIl■Oil CH.Cffi CH.Cff H ■ C.H% C .H, CII■C: CH CH.C:CH ■ ■ C.H, R+? C.l1, CH!C3CH cozc=co 11 H C!us C.H, CHffiC:CI CI.CECH 11 11 CtHs C1l{S C113 NO. F C}l , c Cl+ 0 C!1, ?O■ F CH2C CH S (hereinafter, blank) When applying the compound of the present invention as a herbicide, suitable carriers such as clay, talc, hentonite, etc. , solid carriers such as diatoms and white carbon, or water, alcohols (isoprobanol, butanol, henzyl alcohol, furfuryl alcohol, etc.), aromatic hydrocarbons (toluene, xylene, etc.), ethers (anisole, etc.), Ketones (cyclohexanone, isophorone, etc.), esters (butyl acetate, etc.), acid amides (N
- methylpyrrolidone, etc.) or halogenated hydrocarbons (
It can be applied by mixing with a liquid carrier such as chlorobenzene, etc.), and if desired, surfactants, emulsifiers, dispersants,
Penetrants, spreading agents, thickeners, anti-freezing agents, anti-caking agents, stabilizers, etc. are added to create any agent such as liquids, emulsions, permanent agents, dry flow agents, flowable agents, powders, granules, etc. It can be put to practical use in a mold.
また、本発明化合物は必要に応じて製剤または散布時に
他種の除草剤、各種殺虫剤、殺菌剤、植物生長調節剤、
共力剤などと混合施用しても良い。In addition, the compound of the present invention may be used as necessary in formulation or spraying with other herbicides, various insecticides, fungicides, plant growth regulators, etc.
It may also be used in combination with a synergist.
混合する除草剤の種類としては、例えば、ファーム・ケ
ミカルズ・ハンドブック(Farm Chemical
sHandbook) 1 9 8 9年版に記載され
ている化合物などがある。その施用薬量は適用場面、施
用時期、施用方法、栽培作物等により差異はあるが一般
には有効成分量としてヘクタール(ha)当たり0.0
5〜lokg程度が適当である。As for the types of herbicides to be mixed, for example, see the Farm Chemicals Handbook (Farm Chemicals Handbook).
sHandbook) 1989 edition. The amount of the applied drug varies depending on the application situation, application time, application method, cultivated crop, etc., but in general, the amount of active ingredient is 0.0 per hectare (ha).
Approximately 5 to 100 kg is appropriate.
次に具体的に本発明化合物を用いる場合の製剤の配合例
を示す。但し本発明の配合例は、これらのみに限定され
るものではない。なお、以下の配合例において「部」は
重量部を意味する。Next, specific formulation examples of formulations using the compounds of the present invention will be shown. However, the formulation examples of the present invention are not limited to these only. In addition, in the following formulation examples, "parts" mean parts by weight.
配合±土 永和剤
本発明化合物No. 2−−−−−−・一・−−−−−
−一−一一一・・−−−−−−5 0部ジークライトP
F P −−−−−−・−−−−−−一一一一・−
4 3部(カオリン系クレ一二
ジークライト工業■商品名)
ソルポール5050−−−−−一−−−−− 2部(
アニオン性界面活性剤:
東邦化学工業■商品名)
ルノックス1 0 0 0 C −−−一.− ・−−
−−一一−−−−−− 3部(アニオン性界面活性剤:
東邦化学工業■商品名)
カーブレシクス#80(固結防止剤)−2部(ホワイト
カーボン:塩野義製薬■商品名)以上を均一に混合粉砕
して水和剤とする。Compound ± Soil Permanent agent Invention compound No. 2--------・1・----
-1-111...---5 Part 0 Sieglite P
F P −−−−−−・−−−−−−1111・−
4 3 parts (Kaolin-based Kreichijikulite Kogyo ■Product name) Solpol 5050---1------ 2 parts (
Anionic surfactant: Toho Chemical Industry ■Product name) Lunox 1 0 0 0 C---1. −・−−
--11-------- 3 parts (anionic surfactant: Toho Chemical Co., Ltd. ■Product name) Carbresix #80 (anti-caking agent) - 2 parts (White carbon: Shionogi & Co., Ltd. ■Product name) or more Mix and grind them uniformly to make a wettable powder.
D泣L乳剤
本発明化合物No. 1 6−−−−−−−・一・一・
一−一−−−〜一一−・− 3部キシレンー−−−−−
−−−−一−−−−−−−−−一・−−−−−−−−−
−−・一−−−−76部イソホロンー−−−−一−.−
−−−−−−−−−−−−−−−− 1 5部ソルボー
ル3 0 0 5 X −−−−−−−−−−−−−−
−−・・−−−− 6部(非イオン性界面活性剤とアニ
オン性界面活性剤との混合物:東邦化学工業■商品名)
以上を均一に混合して乳剤とする。D-L Emulsion Invention Compound No. 1 6--------・1・1・
1-1----~11-・- 3 parts xylene---
−−−−1−−−−−−−−−1・−−−−−−−−−
--・1----76 parts isophorone---1-. −
−−−−−−−−−−−−−−−− 1 5 parts Solbol 3 0 0 5 X −−−−−−−−−−−−−−
−−・・−−−− 6 parts (Mixture of nonionic surfactant and anionic surfactant: Toho Chemical Industry ■Product name)
The above is mixed uniformly to form an emulsion.
配治.111 フロアブル剤
本発明化合物陥. l 8 −−−−−−一一一−−−
−−−−−・− 35部アグリゾールS−7 1 1
−−−−−−−− 8部(非イオン性界面活性剤:花
王■商品名)ルノックス1 0 0 0 C −−−−
一・−・−−−−−−一一一一・−0.5部(アニオン
性界面活性剤:
東邦化学工業■商品名)
1%ロドポール水一−−−−−一−一−−−一−−一一
−一・一−−−−− 2 0部(増粘剤:ローン・プ
ーラン社商品名)エチレングリコール(凍結防止剤)
− 8部水−−〜−−−−−−一−一−−−−−−−−
−一・・一−−−−−−−−−−−一一−−28.5部
以上を均一に混合して、フロアブル剤とする。Management. 111 Flowable agent Compound of the present invention. l 8 -------111---
-------・- 35 parts Agrisol S-7 1 1
------- 8 parts (nonionic surfactant: Kao brand name) Lunox 1 0 0 0 C ----
1・−・−−−−−−1111・−0.5 part (anionic surfactant: Toho Chemical Industry ■Product name) 1% Rhodopol water 1−−−−1−1−−− 1--11-1.1----- 2 0 parts (thickener: Lone-Poulenc brand name) ethylene glycol (antifreeze agent)
− 8 parts water −−−−−−−−1−1 −−−−−−−
-1..1--11--28.5 parts or more are mixed uniformly to form a flowable agent.
ロ虹粒剤
本発明化合物No. 2−−−−−−−−−・−一−−
−−−−・− 0. 1部ペントナイト ー−−−−・
−−−−−−−一−一−−〜−−−−−−−−−−5
5. 0部タルクー−−−−−−−−−−一−−一−−
−−−−一−−・−−− −−−−−−−−−− 4
4. 9部以上を均一に混合粉砕した後、少量の水を加
えて撹拌混合捏和し、押出式造粒機で造粒し、乾燥して
粒剤にする。(b) Rainbow granules Compound No. of the present invention. 2−−−−−−−−−・−1−−
------・- 0. Part 1 Pentonite ------
−−−−−−−1−1−−−−−−−−−−5
5. Part 0 Tarku---------1---1---
−−−−1−−・−−− −−−−−−−−−− 4
4. After 9 parts or more are uniformly mixed and pulverized, a small amount of water is added, stirred and kneaded, granulated using an extrusion granulator, and dried to form granules.
ffili 粒状永和剤(ドライフロアブル剤)本発
明化合物No. 1 6−−−−−−−−−一−− 7
5部イソバンNo. 1−−−−−−−−−−−−−
−−−−−−−−−−一−− 1 0部(アニオン性界
面活性剤:
クラレイソプレンケミカル■商品名)
ハニレックスN−−−−−−一−−−−−−−−...
...5部(アニオン性界面活性剤:
山陽国策パルプ■商品名)
カーブレックス# 8 0−−−一−−−−−−−−−
−−−−−1 0部(ホワイトカーボン:塩野義製薬■
商品名)以上を均一に混合微粉砕してドライフロアブル
剤とする。ffili Granular Permanent Agent (Dry Flowable Agent) Present Compound No. 1 6----------1-- 7
5 parts isobane no. 1------------
--------------1-- 10 parts (Anionic surfactant: Clareisoprene Chemical ■Product name) Honeylex N----------1--------. .. ..
.. .. .. 5 parts (Anionic surfactant: Sanyo Kokusaku Pulp ■Product name) Carbrex #8 0---1---------
------1 0 copies (White Carbon: Shionogi & Co., Ltd. ■
Product name) The above is mixed and pulverized uniformly to make a dry flowable agent.
使用に際しては上記水和剤、乳剤、ドライフロアブル剤
、フロアブル剤は水で50〜1000倍に希釈して、有
効成分が1ヘクタール(ha)当たり0.001〜2k
gになるように散布する。When using, the above-mentioned hydrating powders, emulsions, dry flowables, and flowables should be diluted 50 to 1000 times with water so that the active ingredients are 0.001 to 2 K/ha.
Spread it so that it becomes g.
次に、本発明化合物の除草剤としての有用性を以下の試
験例において具体的に説明する。Next, the usefulness of the compounds of the present invention as herbicides will be specifically explained in the following test examples.
1K験一仔トニ」一 土壌処理による除草効果試験N
l 5 cm、横22cm、深さ6C!I+のプラスチ
ック製箱に殺菌した洪積土壌を入れ、イヌホーズキ、ハ
キダメギク、イヌガラシ、トウモロコシ、コムギ、ダイ
ズを混挿し、約1 cm覆土した後有効成分量が所定の
割合となるように土壌表面へ小型スプレーで均一に散布
した。散布の際の薬液は、前記配合例等に準じて適宜調
整された製剤を水で希釈して用い、これを散布した。薬
液散布3週間後にダイズ、トウモロコシ、コムギおよび
各種雑草に対する除草効果を下記の判定基準に従い調査
した。1K test Ichiko Toni'1 Weeding effect test by soil treatment N
L 5cm, width 22cm, depth 6C! Fill an I+ plastic box with sterilized diluvial soil, interplant it with Japanese dogbuck, leafminer, dogwood, corn, wheat, and soybean, cover it with soil to a depth of about 1 cm, and then spread it onto the soil surface in small pieces so that the amount of active ingredients is at the predetermined ratio. Spread it evenly with a sprayer. The chemical solution used for spraying was a formulation suitably prepared according to the formulation example described above, diluted with water, and used for spraying. Three weeks after spraying the chemical solution, the herbicidal effects on soybean, corn, wheat, and various weeds were investigated according to the following criteria.
結果を第6表に示す。The results are shown in Table 6.
判定基準
5・・・殺草率 90%以上(ほとんど完全枯死)4・
・・殺草率 70〜90%
3・・・殺草率 40〜70%
2・・・殺草率 20〜40%
l・・・殺草率 5〜20%
0・・・殺草率 5%以下(ほとんど効力なし)但し
、上記の殺草率は、薬剤処理区の地上部生草重および無
処理区の地上部生草重を判定して下記の式により求めた
ものである。Judgment Criterion 5: Weed killing rate 90% or more (almost complete death) 4.
... Weed killing rate 70-90% 3... Weed killing rate 40-70% 2... Weed killing rate 20-40% l... Weed killing rate 5-20% 0... Weed killing rate 5% or less (almost effective) (None) However, the above weed killing rate was determined by the following formula by determining the above-ground fresh grass weight in the chemical-treated plot and the above-ground fresh grass weight in the non-treated plot.
跋駿1二1 茎葉処理による除草効果試験縦15cm、
横22cm、深さ6cmのプラスチック製箱に殺菌した
洪積土壌を入れ、イヌホーズキ、ハキダメギク、イヌガ
ラシ、トウモロコシ、コムギ、ダイズの種子をそれぞれ
スポット状に播種し、約l can覆土した。各種植物
が2〜3葉期に達したとき、有効成分量が所定の割合と
なるように茎葉部へ均一に散布した。Hashun 121 Weeding effect test by foliage treatment 15cm long,
Sterilized diluvial soil was placed in a plastic box measuring 22 cm wide and 6 cm deep, and seeds of dogfish, leafminer, dogberry, corn, wheat, and soybean were sown in spots, and covered with about 1 can of soil. When each plant reached the 2-3 leaf stage, the active ingredient was uniformly sprayed onto the stems and leaves so that the amount of the active ingredient was at a predetermined ratio.
散布の際の薬液は、前記配合例等に準じて適宜調整され
た製剤を水で希釈して用い、これを小型スプレーで各種
雑草および作物の茎葉部の全面に散布した。薬液散布4
週間後に各種雑草に対する除草効果または各種作物に対
する薬害を試験例lの判定基準に従い調査した。結果を
第7表に示す。The chemical solution used for spraying was prepared appropriately according to the formulation example described above, diluted with water, and sprayed using a small sprayer over the entire foliage of various weeds and crops. Chemical spraying 4
After a week, the herbicidal effects on various weeds and the phytotoxicity on various crops were investigated according to the criteria in Test Example 1. The results are shown in Table 7.
(以下、余白) 第 6表 化合物 薬量 No. ( g / a ) 且旦土工WS 2 0.4 0.8 1.6 554000 555000 555000 l0 1.6 5 4 3 0 0 3 14 1.6 5 5 4 0 0 0 l6 0.4 0.8 1.6 555000 555000 555000 l8 0.4 0.8 1.6 554000 555000 555000 22 1.6 5 5 5 0 0 0 比較対照 化合物A4.0 4 5 4 4 5 4 第 7表 化合物 薬量 No. ( g / a ) 廿旦土工W昼 2 0.4 0.8 1.6 553001 554002 554003 lO 1.6 5 5 5 0 0 0 l4 1.6 5 5 4 0 0 2 16 0.4 0.8 1.6 542000 554001 555002 18 0、4 0.8 1,6 552000 554000 555001 22 1.6 5 5 3 0 0 0 比較対照 化合物A 4.0 4 2 3 4 5 5 尚、第6、第7表中の記号は次の意味を示す。(Hereafter, margin) No. Table 6 Compound Dosage No. (g/a) Andan Earthworks WS 2 0.4 0.8 1.6 554,000 555,000 555,000 l0 1.6 5 4 3 0 0 3 14 1.6 5 5 4 0 0 0 l6 0.4 0.8 1.6 555,000 555,000 555,000 l8 0.4 0.8 1.6 554,000 555,000 555,000 22 1.6 5 5 5 0 0 0 compare and contrast Compound A4.0 4 5 4 4 5 4 No. Table 7 Compound Dosage No. (g/a) Hattan earthworks W noon 2 0.4 0.8 1.6 553001 554002 554003 lO 1.6 5 5 5 0 0 0 l4 1.6 5 5 4 0 0 2 16 0.4 0.8 1.6 542000 554001 555002 18 0, 4 0.8 1,6 552,000 554,000 555001 22 1.6 5 5 3 0 0 0 compare and contrast Compound A 4.0 4 2 3 4 5 5 The symbols in Tables 6 and 7 have the following meanings.
且(イヌホーズキ)、 ■(ハキダメギク)、1 (イ
ヌガラシ)、 工(トウモロコシ)、W(コムギ)、
Σ(ダイズ)。且(Dogweed), ■(Dogberry), 1 (Dogberry), Work (Corn), W (Wheat),
Σ (soybean).
比較対照化合物Aは H 一般名:ブロマシル を示す。Comparative control compound A is H Generic name: Bromacil shows.
(Bromacil )
(以下、
余白)
試刺トユ 温水条件における除草効果試験1 /500
0アールのワグネルポット中に沖積土壌を入れた後、水
を入れて混和し水深2CD+の淡水条件とする。タイヌ
ビエ、コナギ、キカシグサ、ホタルイのそれぞれの種子
を、上記のポットに混播し、又、ミズガヤツリ、ウリカ
ワの塊茎を置床した後、2.5葉朋のイネ苗を移植した
。ポットを25〜30゜Cの温室内に置いて植物を育成
し、播種後2日目に水面へ所定の薬量になるように、薬
剤希釈液をメスピペットで滴下処理した。薬液滴下後3
週目にイネおよび各種雑草に対する除草効果を試験例一
lの判定基準に従って調査した。結果を第8表に示す。(Bromacil) (Hereinafter, blank) Trial sting Toyu Herbicidal effect test under warm water conditions 1 /500
After putting alluvial soil in a Wagner pot of 0 are, water is added and mixed to create a freshwater condition with a water depth of 2 CD+. Seeds of Japanese millet, Konagi, Kikashigusa, and Firefly were mixedly sown in the above-mentioned pots, and tubers of Mizugaya cyperus and Urikawa were placed in the beds, and then rice seedlings of 2.5 leaves were transplanted. The pots were placed in a greenhouse at 25 to 30°C to grow the plants, and on the second day after sowing, a diluted drug solution was dropped onto the water surface using a measuring pipette in a predetermined amount. After dropping the chemical solution 3
After a week, the herbicidal effect on rice and various weeds was investigated according to the criteria in Test Example 11. The results are shown in Table 8.
(以下,余白)
第
8
表
2
0.4 3 4 5 5 3
4 00.8 4 5 5 5
4 5 01.6 5 5
5 5 5 5 016
0.4 4 4 5 5 3
4 00.8 5 5 5 5
4 5 01.6 5 5
5 5 5 5 0l8
0.4 3 4 4 5 3 3
00.8 4 5 5 5
4 4 01.6 5 5 5
5 5 5 0手
続
補
正
書(自発)
平成
3年
3月1
l
日
1.
事件の表示
平成2年特許願第8827号
2.
発明の名称
6−アリールー2,
4
(IH,
3H)
−ピリ
ミジンジオン誘導体および除草剤
3.
補正をする者
事件との関係(Hereafter, blank space) Table 8 0.4 3 4 5 5 3
4 00.8 4 5 5 5
4 5 01.6 5 5
5 5 5 5 016 0.4 4 4 5 5 3
4 00.8 5 5 5 5
4 5 01.6 5 5
5 5 5 5 0l8 0.4 3 4 4 5 3 3
00.8 4 5 5 5
4 4 01.6 5 5 5
5 5 5 0 Written amendment (voluntary) March 1, 1991 Day 1. Case Description 1990 Patent Application No. 8827 2. Title of the invention 6-aryl 2,4 (IH, 3H) -pyrimidinedione derivatives and herbicides3. Relationship with the case of the person making the amendment
Claims (2)
それぞれ独立して水素原子、C_1_〜_4アルキル、
C_1_〜_4ハロアルキル、ハロゲン原子、シアノ、
ニトロ、C_1_〜_4アルコキシ、C_1_〜_4ハ
ロアルコキシ、C_1_〜_4アルキルカルボニルまた
はC_1_〜_4アルコキシカルボニルを示し、R_6
は水素原子、C_1_〜_4アルキルまたはC_1_〜
_4ハロアルキルを示し、 R_7は水素原子、C_1_〜_4アルキル、ハロゲン
原子またはニトロを示し、 R_8は水素原子またはハロゲン原子を示し、R_9は
ハロゲン原子またはニトロを示し、R_1_0は水素原
子、ハロゲン原子、シアノ、ニトロ、NR_1_1R_
1_2(R_1_1,R_1_2はそれぞれ独立して水
素原子、C_1_〜_4アルキル、C_1_〜_4アル
キルカルボニル、C_1_〜_4アルコキシカルボニル
またはC_1_〜_4アルキルスルホニルを示す。)、 CO_2R_1_3(R_1_3は水素原子、ナトリウ
ム、C_1_〜_4アルキル、C_3_〜_6シクロア
ルキル、C_2_〜_5アルケニル、C_3_〜_5ア
ルキニル、フェニルまたはベンジルを示す。)、OR_
1_4,SR_1_4(R_1_4は水素原子、C_1
_〜_4アルキル、C_3_〜_6シクロアルキル、C
_2_〜_5アルケニルまたはC_3_〜_5アルキニ
ルを示す。)または ▲数式、化学式、表等があります▼,▲数式、化学式、
表等があります▼(R_1_5は水素原子またはC_1
_〜_4アルキルを示し、R_1_6は水素原子、ナト
リウム、C_1_〜_5アルキル、C_3_〜_6シク
ロアルキル、C_2_〜_5アルケニル、C_3_〜_
5アルキニル、フェニルまたはベンジルを示す。)を示
し、 Xは酸素原子または硫黄原子を示す。〕で表されるウラ
シル誘導体と、R_9とR_1_0が環を形成する場合
式(II)、(III) ▲数式、化学式、表等があります▼(II) ▲数式、化学式、表等があります▼(III) 〔式中、R_1,R_2,R_3,R_4,R_5,R
_6,R_7,R_8,Xは前記と同様の意味を表し、 R_1_7は水素原子、C_1_〜_4アルキル、C_
2_〜_5アルケニル、C_3_〜_5アルキニル、ベ
ンジル、C_1_〜_4ハロアルキル、▲数式、化学式
、表等があります▼,CH_2CN,CH_2CONH
_2またはCH_2OHを示す。〕で表されるウラシル
誘導体。(1) Formula (I) ▲There are mathematical formulas, chemical formulas, tables, etc.▼(I) [In the formula, R_1, R_2, R_3, R_4, R_5 are
Each independently hydrogen atom, C_1_~_4 alkyl,
C_1_~_4 haloalkyl, halogen atom, cyano,
Nitro, C_1_-_4 alkoxy, C_1_-_4 haloalkoxy, C_1_-_4 alkylcarbonyl or C_1_-_4 alkoxycarbonyl, R_6
is a hydrogen atom, C_1_~_4 alkyl or C_1_~
_4 represents haloalkyl, R_7 represents a hydrogen atom, C_1_ to _4 alkyl, a halogen atom or nitro, R_8 represents a hydrogen atom or a halogen atom, R_9 represents a halogen atom or nitro, R_1_0 represents a hydrogen atom, a halogen atom, a cyano atom, , Nitro, NR_1_1R_
1_2 (R_1_1, R_1_2 each independently represent a hydrogen atom, C_1_-_4 alkyl, C_1_-_4 alkylcarbonyl, C_1_-_4 alkoxycarbonyl or C_1_-_4 alkylsulfonyl.), CO_2R_1_3 (R_1_3 is a hydrogen atom, sodium, C_1_ ~_4 alkyl, C_3_-_6 cycloalkyl, C_2_-_5 alkenyl, C_3_-_5 alkynyl, phenyl or benzyl.), OR_
1_4, SR_1_4 (R_1_4 is a hydrogen atom, C_1
___~_4 alkyl, C_3_~_6 cycloalkyl, C
Indicates _2_-_5 alkenyl or C_3_-_5 alkynyl. ) or ▲Mathematical formulas, chemical formulas, tables, etc.▼、▲Mathematical formulas, chemical formulas,
There are tables, etc. ▼ (R_1_5 is a hydrogen atom or C_1
_~_4 alkyl, R_1_6 is a hydrogen atom, sodium, C_1_-_5 alkyl, C_3_-_6 cycloalkyl, C_2_-_5 alkenyl, C_3_-_
5 represents alkynyl, phenyl or benzyl. ), and X represents an oxygen atom or a sulfur atom. ] When the uracil derivative represented by R_9 and R_1_0 form a ring, formulas (II), (III) ▲There are mathematical formulas, chemical formulas, tables, etc.▼(II) ▲There are mathematical formulas, chemical formulas, tables, etc.▼( III) [In the formula, R_1, R_2, R_3, R_4, R_5, R
_6, R_7, R_8, X represent the same meanings as above, R_1_7 is a hydrogen atom, C_1_-_4 alkyl, C_
2_~_5 alkenyl, C_3_~_5 alkynyl, benzyl, C_1_~_4 haloalkyl, ▲ Numerical formulas, chemical formulas, tables, etc. are available ▼, CH_2CN, CH_2CONH
Indicates _2 or CH_2OH. ] Uracil derivative represented by.
を特徴とする除草剤。(2) A herbicide comprising the compound according to claim (1) as an active ingredient.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2008827A JPH03215476A (en) | 1990-01-18 | 1990-01-18 | 6-aryl-2,4(1h,3h)-pyrimidinedione derivative and herbicide |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2008827A JPH03215476A (en) | 1990-01-18 | 1990-01-18 | 6-aryl-2,4(1h,3h)-pyrimidinedione derivative and herbicide |
Publications (1)
Publication Number | Publication Date |
---|---|
JPH03215476A true JPH03215476A (en) | 1991-09-20 |
Family
ID=11703629
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2008827A Pending JPH03215476A (en) | 1990-01-18 | 1990-01-18 | 6-aryl-2,4(1h,3h)-pyrimidinedione derivative and herbicide |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPH03215476A (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6355799B1 (en) * | 1997-10-27 | 2002-03-12 | Isk Americas Incorporated | Substituted benzene compounds, process for their preparation, and herbicidal and defoliant compositions containing them |
-
1990
- 1990-01-18 JP JP2008827A patent/JPH03215476A/en active Pending
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6355799B1 (en) * | 1997-10-27 | 2002-03-12 | Isk Americas Incorporated | Substituted benzene compounds, process for their preparation, and herbicidal and defoliant compositions containing them |
US6545161B2 (en) | 1997-10-27 | 2003-04-08 | Isk Americas Incorporated | Substituted benzene compounds, process for their preparation, and herbicidal and defoliant compositions containing them |
USRE39590E1 (en) * | 1997-10-27 | 2007-04-24 | Isk Americas Incorporated | Substituted benzene compounds, process for their preparation, and herbicidal and defoliant compositions containing them |
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