JPH0710844B2 - Pyridine carboxamide - Google Patents
Pyridine carboxamideInfo
- Publication number
- JPH0710844B2 JPH0710844B2 JP21182285A JP21182285A JPH0710844B2 JP H0710844 B2 JPH0710844 B2 JP H0710844B2 JP 21182285 A JP21182285 A JP 21182285A JP 21182285 A JP21182285 A JP 21182285A JP H0710844 B2 JPH0710844 B2 JP H0710844B2
- Authority
- JP
- Japan
- Prior art keywords
- oxo
- dimethyl
- dihydro
- formula
- pyridinecarboxamide
- 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.)
- Expired - Lifetime
Links
- IBBMAWULFFBRKK-UHFFFAOYSA-N picolinamide Chemical compound NC(=O)C1=CC=CC=N1 IBBMAWULFFBRKK-UHFFFAOYSA-N 0.000 title description 2
- 150000003839 salts Chemical class 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical class NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 description 16
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 238000000034 method Methods 0.000 description 11
- -1 4-pyridone compound Chemical class 0.000 description 7
- YWTRXACYCWOQMR-FPLPWBNLSA-N (z)-3-amino-n-phenylbut-2-enamide Chemical class C\C(N)=C\C(=O)NC1=CC=CC=C1 YWTRXACYCWOQMR-FPLPWBNLSA-N 0.000 description 4
- 239000004563 wettable powder Substances 0.000 description 4
- BHHGXPLMPWCGHP-UHFFFAOYSA-N Phenethylamine Chemical compound NCCC1=CC=CC=C1 BHHGXPLMPWCGHP-UHFFFAOYSA-N 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 230000009036 growth inhibition Effects 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- XFRBXZCBOYNMJP-UHFFFAOYSA-N 2,2,6-trimethyl-1,3-dioxin-4-one Chemical compound CC1=CC(=O)OC(C)(C)O1 XFRBXZCBOYNMJP-UHFFFAOYSA-N 0.000 description 2
- SXBRRFLLEOHXIO-UHFFFAOYSA-N 2,6-dimethyl-4-oxo-1h-pyridine-3-carboxylic acid Chemical class CC1=CC(=O)C(C(O)=O)=C(C)N1 SXBRRFLLEOHXIO-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 230000003110 anti-inflammatory effect Effects 0.000 description 2
- 230000018044 dehydration Effects 0.000 description 2
- 238000006297 dehydration reaction Methods 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 230000012010 growth Effects 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- 150000007529 inorganic bases Chemical class 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- AABAITPZTKADCL-UHFFFAOYSA-N 1-benzyl-2,6-dimethyl-4-oxo-n-phenylpyridine-3-carboxamide Chemical compound CC=1N(CC=2C=CC=CC=2)C(C)=CC(=O)C=1C(=O)NC1=CC=CC=C1 AABAITPZTKADCL-UHFFFAOYSA-N 0.000 description 1
- ONMIVFDQMQBKPI-UHFFFAOYSA-N 1-benzyl-n-(4-methoxyphenyl)-2,6-dimethyl-4-oxopyridine-3-carboxamide Chemical compound C1=CC(OC)=CC=C1NC(=O)C(C(C=C1C)=O)=C(C)N1CC1=CC=CC=C1 ONMIVFDQMQBKPI-UHFFFAOYSA-N 0.000 description 1
- XNMPOLGMSVHZFT-UHFFFAOYSA-N 2,6-dimethyl-4-oxo-n,1-diphenylpyridine-3-carboxamide Chemical class CC=1N(C=2C=CC=CC=2)C(C)=CC(=O)C=1C(=O)NC1=CC=CC=C1 XNMPOLGMSVHZFT-UHFFFAOYSA-N 0.000 description 1
- AUGDHDJZMNDHTE-UHFFFAOYSA-N 2,6-dimethyl-4-oxo-n-phenylpyran-3-carboxamide Chemical compound O1C(C)=CC(=O)C(C(=O)NC=2C=CC=CC=2)=C1C AUGDHDJZMNDHTE-UHFFFAOYSA-N 0.000 description 1
- MBIWWPKSHKFRRK-UHFFFAOYSA-N 2-ethyl-2,6-dimethyl-1,3-dioxin-4-one Chemical compound CCC1(C)OC(C)=CC(=O)O1 MBIWWPKSHKFRRK-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 240000007594 Oryza sativa Species 0.000 description 1
- 235000007164 Oryza sativa Nutrition 0.000 description 1
- 235000005733 Raphanus sativus var niger Nutrition 0.000 description 1
- 235000006140 Raphanus sativus var sativus Nutrition 0.000 description 1
- 240000001970 Raphanus sativus var. sativus Species 0.000 description 1
- 241000244155 Taenia Species 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 125000002490 anilino group Chemical class [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 239000000440 bentonite Substances 0.000 description 1
- 229910000278 bentonite Inorganic materials 0.000 description 1
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000002561 ketenes Chemical class 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000013011 mating Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- QVGWUAJALZUURI-UHFFFAOYSA-N n,1-dibutyl-2,6-dimethyl-4-oxopyridine-3-carboxamide Chemical compound CCCCNC(=O)C1=C(C)N(CCCC)C(C)=CC1=O QVGWUAJALZUURI-UHFFFAOYSA-N 0.000 description 1
- YRZJAIPSKODAMK-UHFFFAOYSA-N n,1-didodecyl-2,6-dimethyl-4-oxopyridine-3-carboxamide Chemical compound CCCCCCCCCCCCNC(=O)C1=C(C)N(CCCCCCCCCCCC)C(C)=CC1=O YRZJAIPSKODAMK-UHFFFAOYSA-N 0.000 description 1
- OHZDYNFVFWLHQE-UHFFFAOYSA-N n-(4-chlorophenyl)-1-ethyl-2,6-dimethyl-4-oxopyridine-3-carboxamide Chemical compound CCN1C(C)=CC(=O)C(C(=O)NC=2C=CC(Cl)=CC=2)=C1C OHZDYNFVFWLHQE-UHFFFAOYSA-N 0.000 description 1
- KVVGIIHOZMXEBQ-UHFFFAOYSA-N n-(4-chlorophenyl)-2,6-dimethyl-4-oxo-1h-pyridine-3-carboxamide Chemical compound N1C(C)=CC(=O)C(C(=O)NC=2C=CC(Cl)=CC=2)=C1C KVVGIIHOZMXEBQ-UHFFFAOYSA-N 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 229960003966 nicotinamide Drugs 0.000 description 1
- 235000005152 nicotinamide Nutrition 0.000 description 1
- 239000011570 nicotinamide Substances 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- SIOXPEMLGUPBBT-UHFFFAOYSA-N picolinic acid Chemical class OC(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-N 0.000 description 1
- 230000008635 plant growth Effects 0.000 description 1
- 239000002373 plant growth inhibitor Substances 0.000 description 1
- 239000005648 plant growth regulator Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Landscapes
- Agricultural Chemicals And Associated Chemicals (AREA)
- Pyridine Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
【発明の詳細な説明】 （産業上の利用分野） 本発明は1,4−ジヒドロ−2,6−ジメチル−４−オキソ−
３−ピリジンカルボキサミドに属する新規化合物に関す
るものである。この発明の化合物は、植物に対して成長
抑制作用を示す、また抗炎症作用を有する。DETAILED DESCRIPTION OF THE INVENTION (Field of Industrial Application) The present invention relates to 1,4-dihydro-2,6-dimethyl-4-oxo-
The present invention relates to a novel compound belonging to 3-pyridinecarboxamide. The compound of the present invention shows a growth inhibitory action on plants and also has an anti-inflammatory action.
（従来の技術） 従来、1,4−ジヒドロ−2,6−ジメチル−４−オキソ−３
−ピリジンカルボキサミドに属する化合物についての記
載は、文献に見いだすことが出来る。加藤鉄三等薬学雑
誌、101,40（1981）には、Ｎ−（４−クロロフェニル）
−1,4−ジヒドロ−2,6−ジメチル−４−オキソ−３−ピ
リジンカルボキサミド、1,4−ジヒドロ−2,6−ジメチル
−４−オキソ−Ｎ−フェニル−１−（フェニルメチル）
−３−ピリジンカルボキサミド,1,4−ジヒドロ−Ｎ−
（４−メトキシフェニル）−2,6−ジメチル−４−オキ
ソ−１−（フェニルメチル）−３−ピリジンカルボキサ
ミドおよびＮ−（４−クロロフェニル）−1,4−ジヒド
ロ−2,6−ジメチル−４−オキソ−１−（フェニルメチ
ル）−３−ピリジンカルボキサミドの４つの化合物が報
告されているが、この文献はケテン誘導体の反応性に関
するものであり、これらの化合物がいかなる分野に利用
されるかについては触れられていない。またカナダ国特
許第1,115,278号〔およびJ.B.Pierce等J.Med.Chem.25,1
31（1982）を参照〕には、抗炎症作用を有する４−ピリ
ドン化合物についての記載が見られ、1,4−ジヒドロ−
2,6−ジメチル−４−オキソ−N,1−ジフェニル−３−ピ
リジンカルボキサミド類、N,1−ジブチル−1,4−ジヒド
ロ−2,6−ジメチル−４−オキソ−３−ピリジンカルボ
キサミド、N,1−ジドデシル−1,4−ジヒドロ−2,6−ジ
メチル−４−オキソ−３−ピリジンカルボキサミドおよ
びＮ−（４−クロロフェニル）−１−エチル−1,4−ジ
ヒドロ−2,6−ジメチル−４−オキソ−３−ピリジンカ
ルボキサミドなどが開示されている。(Prior Art) Conventionally, 1,4-dihydro-2,6-dimethyl-4-oxo-3
Descriptions of the compounds belonging to the pyridinecarboxamide can be found in the literature. Kato Tetsuzo Pharmaceutical Journal, 101, 40 (1981), N- (4-chlorophenyl)
-1,4-dihydro-2,6-dimethyl-4-oxo-3-pyridinecarboxamide, 1,4-dihydro-2,6-dimethyl-4-oxo-N-phenyl-1- (phenylmethyl)
-3-Pyridinecarboxamide, 1,4-dihydro-N-
(4-Methoxyphenyl) -2,6-dimethyl-4-oxo-1- (phenylmethyl) -3-pyridinecarboxamide and N- (4-chlorophenyl) -1,4-dihydro-2,6-dimethyl-4 Although four compounds of -oxo-1- (phenylmethyl) -3-pyridinecarboxamide have been reported, this document relates to the reactivity of ketene derivatives, and to which field these compounds are used. Has not been touched. Also, Canadian Patent No. 1,115,278 [and JB Pierce et al. J. Med. Chem. 25, 1
31 (1982)], there is a description of a 4-pyridone compound having an anti-inflammatory action, and 1,4-dihydro-
2,6-Dimethyl-4-oxo-N, 1-diphenyl-3-pyridinecarboxamides, N, 1-dibutyl-1,4-dihydro-2,6-dimethyl-4-oxo-3-pyridinecarboxamide, N , 1-Didodecyl-1,4-dihydro-2,6-dimethyl-4-oxo-3-pyridinecarboxamide and N- (4-chlorophenyl) -1-ethyl-1,4-dihydro-2,6-dimethyl- 4-oxo-3-pyridinecarboxamide and the like are disclosed.
一方、植物成長調整剤、特に化学的交配剤として活性を
示す化合物として、1,4−ジヒドロ−４−オキソ−３−
ピリジンカルボン酸の誘導体が知られているが（特開昭
59−144676、特開昭57−114573）、化合物（Ｉ）のよう
な、1,4−ジヒドロ−2,6−ジメチル−４−オキソ−３−
ピリジンカルボキサミド化合物を有効成分とする植物成
長抑制剤は知られていなかった。本発明は、1,4−ジヒ
ドロ−2,6−ジメチル−４−オキソ−３−ピリジンカル
ボキサミド化合物に属する一群の新規化合物を提供する
ものである。On the other hand, as a compound showing activity as a plant growth regulator, particularly a chemical mating agent, 1,4-dihydro-4-oxo-3-
Although derivatives of pyridinecarboxylic acid are known,
59-144676, JP-A-57-114573), 1,4-dihydro-2,6-dimethyl-4-oxo-3-, such as compound (I).
A plant growth inhibitor containing a pyridinecarboxamide compound as an active ingredient has not been known. The present invention provides a group of novel compounds belonging to the 1,4-dihydro-2,6-dimethyl-4-oxo-3-pyridinecarboxamide compound.
（目的と構成） 本発明は、下記の式（Ｉ）で示される化合物及びその付
加塩を提供するものである。(Object and Structure) The present invention provides a compound represented by the following formula (I) and an addition salt thereof.
〔式中R1とR2はベンゼン環の3,4又は５位に結合し、同
一又は異なって水素原子、ハロゲン原子、低級アルキル
基、ハロゲン化低級アルキル基、又は低級アルコキシ基
をそれぞれ意味する。〕 この発明で、低級アルキル基、低級アルコキシ基などで
用いた用語《低級》とは、C1〜C5の炭素原子を含有する
基を意味する。具体的には、メチル、エチル、プロピ
ル、イソプロピル、ブチル、イソブチル、ペンチル、イ
ソペンチルのような低級アルキル基、メトキシ、エトキ
シ、プロポキシ、イソプロポキシ、ブトキシのような低
級アルコキシ基が挙げられる。 [Wherein R 1 and R 2 are bonded to the 3, 4 or 5 position of the benzene ring and are the same or different and each represents a hydrogen atom, a halogen atom, a lower alkyl group, a halogenated lower alkyl group or a lower alkoxy group. . In the present invention, the term “lower” used for a lower alkyl group, a lower alkoxy group and the like means a group containing a C 1 to C 5 carbon atom. Specific examples include lower alkyl groups such as methyl, ethyl, propyl, isopropyl, butyl, isobutyl, pentyl and isopentyl, and lower alkoxy groups such as methoxy, ethoxy, propoxy, isopropoxy and butoxy.
ハロゲン原子には、塩素、臭素又はフッ素原子が含まれ
る。Halogen atoms include chlorine, bromine or fluorine atoms.
本発明の式（Ｉ）の化合物は、塩基性を示すとき、塩
酸、硫酸、リン酸、メタンスルホン酸、パラトルエンス
ルホン酸、トリフルオロ酢酸などの酸との付加塩、また
分子内にカルボキシル基が存在するとき無機塩基との付
加塩を形成しうる。このような付加塩もこの発明の範囲
に含まれる。When the compound of formula (I) of the present invention shows basicity, it is an addition salt with an acid such as hydrochloric acid, sulfuric acid, phosphoric acid, methanesulfonic acid, paratoluenesulfonic acid, trifluoroacetic acid, or a carboxyl group in the molecule. May form an addition salt with an inorganic base. Such addition salts are also included in the scope of the present invention.
この発明の式（Ｉ）の化合物は、次に示す方法で作るこ
とができる。The compounds of formula (I) of this invention can be made by the following methods.
（方法Ａ） 〔式（II）中R1及びR2は、式（Ｉ）の定義と同一〕 この方法は、３−アミノクロトン酸アニリド誘導体（I
I）と2,2,6−トリメチル−4H−1,3−ジオキシン−４−
オンとを適当な溶媒（たとえばトルエン、キシレンな
ど）中、加熱下（たとえば約100℃〜140℃）に反応させ
ることによって行なわれる。ここで、2,2,6−トリメチ
ル−4H−1,3−ジオキシン−４−オンの代りに、２−エ
チル−2,6−ジメチル−4H−1,3−ジオキシン−４−オン
を用いることも可能である。また、この方法を行なうに
当っては、３−アミノクロトン酸アニリド誘導体（II）
は、単離された物質を用いる必要はなくPhCH2CH2NH2（I
II）と 式（IV）： （式（IV）中、R1、R2は式（Ｉ）の定義と同一） との反応混合物のままを直接用いてもよい。実際上は、
この反応混合物を用いるのがより簡便である。(Method A) [Wherein R 1 and R 2 in the formula (II) are the same as the definition in the formula (I)] This method is carried out by using the 3-aminocrotonic acid anilide derivative (I
I) and 2,2,6-trimethyl-4H-1,3-dioxin-4-
It is carried out by reacting the on with a suitable solvent (eg, toluene, xylene, etc.) under heating (eg, about 100 ° C. to 140 ° C.). Here, using 2-ethyl-2,6-dimethyl-4H-1,3-dioxin-4-one instead of 2,2,6-trimethyl-4H-1,3-dioxin-4-one Is also possible. In performing this method, 3-aminocrotonic acid anilide derivative (II)
Does not require the use of isolated material, but PhCH 2 CH 2 NH 2 (I
II) and formula (IV): (In the formula (IV), R 1 and R 2 are the same as the definition in the formula (I)), and the reaction mixture itself may be directly used. In fact,
It is more convenient to use this reaction mixture.
（方法Ｂ） （式（Ｖ）中、R1、R2は式（Ｉ）の定義と同一） この方法は、式（Ｉ）に対応する４−ピロン化合物
（Ｖ）、すなわち2,6−ジメチル−４−オキソ−Ｎ−フ
ェニル−4H−ピラン−３−カルボキサミドと式（III）
で表わされるβ−フェネチルアミン又はその塩とを適当
な溶媒（たとえば、エタノール、水など）中で室温〜60
℃位の温度で反応させるものである。使用するβ−フェ
ネチルアミンの量は４−ピロン化合物に対して等モル以
上、必要な場合には大過剰量が用いられる。アミンが塩
として入手される場合には、中和量以上の有機もしくは
無機塩基によって、アミンを遊離の形で反応に供するこ
とが必要である。(Method B) (In the formula (V), R 1 and R 2 are the same as the definition of the formula (I)) This method is carried out by using the 4-pyrone compound (V) corresponding to the formula (I), that is, 2,6-dimethyl-4- Oxo-N-phenyl-4H-pyran-3-carboxamide and formula (III)
Β-phenethylamine represented by or a salt thereof in a suitable solvent (eg, ethanol, water, etc.) at room temperature to 60
The reaction is performed at a temperature of about ° C. The amount of β-phenethylamine used is equimolar or more to the 4-pyrone compound, and a large excess amount is used if necessary. When the amine is obtained as a salt, it is necessary to provide the amine in a free form with a neutralizing amount or more of an organic or inorganic base.
（方法Ｃ） 〔式（VII）中のR1、R2は式（Ｉ）の定義と同一〕 この方法は式（Ｉ）に対応するカルボン酸すなわち1,4
−ジヒドロ−2,6−ジメチル−４−オキソ−３−ピリジ
ンカルボン誘導体（VI）とアニリン誘導体（VII）とを
脱水縮合剤の存在下で反応させるものである。この方法
を実際に行なう場合は、例えば特開昭52−57102号に記
載の１−置換−２−ハロピリジニウム塩と第三アミンと
を脱水縮合剤として用いる方法が有利に利用できる。(Method C) [Wherein R 1 and R 2 in formula (VII) are the same as defined in formula (I)] This method is based on the carboxylic acid corresponding to formula (I), namely 1,4
-Dihydro-2,6-dimethyl-4-oxo-3-pyridine carboxylic derivative (VI) and aniline derivative (VII) are reacted in the presence of a dehydration condensing agent. When this method is actually carried out, for example, the method described in JP-A-52-57102, which uses a 1-substituted-2-halopyridinium salt and a tertiary amine as a dehydration condensation agent, can be advantageously used.
以下この発明を実施例によって説明する。またこの発明
の化合物の植物に対する成長抑制作用を示す。The present invention will be described below with reference to examples. Further, the compound of the present invention exhibits a plant growth inhibitory action.
実施例１ 1,4−ジヒドロ−2,6−ジメチル−４−オキソ−Ｎ−フェ
ニル−１−（２−フェニルエチル）−３−ピリジンカル
ボキサミド アセトアセトアニリド2.53g（14.3mmol）、β−フェネ
チルアミン1.73g（14.3mmol）およびトルエン20mlの混
合物を1.5時間加熱還流し、その間に生成した水をトル
エン約6mlを共に留出させた。加熱を継続しながら、2,
2,6−トリメチル−4H−1,3−ジオキシン−４−オン5.10
g（35.8mmol）のトルエン（10ml）溶液を約30分間かけ
て滴下し、さらに20分間加熱還流を続けた後、反応混合
物を室温まで放冷した。生じた結晶を瀘別洗浄し、減圧
下に乾燥すると、題記化合物1.79gが得られた。融点178
−181.5℃。Example 1 1,4-dihydro-2,6-dimethyl-4-oxo-N-phenyl-1- (2-phenylethyl) -3-pyridinecarboxamide acetoacetanilide 2.53 g (14.3 mmol), β-phenethylamine 1.73 g A mixture of (14.3 mmol) and 20 ml of toluene was heated under reflux for 1.5 hours, and about 6 ml of toluene was distilled out together with water generated during the heating. While continuing to heat 2,
2,6-Trimethyl-4H-1,3-dioxin-4-one 5.10
A solution of g (35.8 mmol) in toluene (10 ml) was added dropwise over about 30 minutes, heating and refluxing were continued for another 20 minutes, and then the reaction mixture was allowed to cool to room temperature. The resulting crystals were filtered and washed, and dried under reduced pressure to give the title compound (1.79 g). Melting point 178
-181.5 ° C.
同様の方法を用いて実施例２〜９の化合物を合成した。The compounds of Examples 2 to 9 were synthesized using the same method.
次に掲げる表１及び表２は本発明に係る化合物の物性等
をまとめたものである。Tables 1 and 2 listed below summarize the physical properties and the like of the compounds according to the present invention.
なお、表２中の“性能評価”とは、次のとおりである。The "performance evaluation" in Table 2 is as follows.
タルク（50重量部）、ベントナイト（25重量部）ソルボ
ール−9047（東邦化学製、２重量部）、ソルボール−50
39（同前、３重量部）を混合しキャリアーを調製した。
テスト化合物50重量部と前記キャリアー200重量部とを
混合し、20％水和剤を作った。この水和剤を純水に分散
させ所定濃度の水和剤分散液を得た。別にイネ、タイヌ
ビエ、二十日ダイコン種子を催芽させたシャーレを用意
し、上記水和剤分散液を添加し、25℃の照明付き定温庫
で７日間育苗して成長程度を観察した。結果の表示法
は、１＝無影響、２＝25％成長抑制、３＝50％成長抑
制、４＝75％成長抑制、５＝完全枯死とする。Talc (50 parts by weight), Bentonite (25 parts by weight) Solball-9047 (manufactured by Toho Chemical Co., 2 parts by weight), Solball-50
39 (the same as above, 3 parts by weight) were mixed to prepare a carrier.
50 parts by weight of the test compound and 200 parts by weight of the carrier were mixed to prepare a 20% wettable powder. This wettable powder was dispersed in pure water to obtain a wettable powder dispersion having a predetermined concentration. Separately, a petri dish in which rice, Taenia serrata, and Japanese radish seeds were germinated was prepared, the above-mentioned wettable powder dispersion was added, and seedlings were grown for 7 days in a constant temperature cabinet at 25 ° C to observe the degree of growth. The results are displayed as follows: 1 = no effect, 2 = 25% growth inhibition, 3 = 50% growth inhibition, 4 = 75% growth inhibition, 5 = complete death.
───────────────────────────────────────────────────── フロントページの続き (72)発明者 森島 靖雄 兵庫県神戸市垂水区つつじが丘３―６―11 (72)発明者 長部 広和 兵庫県姫路市網干区新在家940 ─────────────────────────────────────────────────── ─── Continuation of the front page (72) Inventor Yasuo Morishima 3-6-11 Tsutsujigaoka, Tarumi-ku, Kobe-shi, Hyogo (72) Inventor Hirokazu Hirobe 940 Newly-owned house, Aboshi-ku, Himeji-shi, Hyogo
Claims (1)
同一又は異なって水素原子、ハロゲン原子、低級アルキ
ル基、ハロゲン化低級アルキル基又は低級アルコキシ基
をそれぞれ意味する。〕 を有する1,4−ジヒドロ−2,6−ジメチル−４−オキソ−
３−ピリジンカルボキサミド化合物及びその付加塩。1. Formula (I): [Wherein R 1 and R 2 are bonded to the 3, 4 or 5 position of the benzene ring,
The same or different, respectively, means a hydrogen atom, a halogen atom, a lower alkyl group, a halogenated lower alkyl group or a lower alkoxy group. ] 1,4-dihydro-2,6-dimethyl-4-oxo- having
3-Pyridinecarboxamide compounds and addition salts thereof.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP21182285A JPH0710844B2 (en) | 1985-09-25 | 1985-09-25 | Pyridine carboxamide |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP21182285A JPH0710844B2 (en) | 1985-09-25 | 1985-09-25 | Pyridine carboxamide |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6272668A JPS6272668A (en) | 1987-04-03 |
| JPH0710844B2 true JPH0710844B2 (en) | 1995-02-08 |
Family
ID=16612166
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP21182285A Expired - Lifetime JPH0710844B2 (en) | 1985-09-25 | 1985-09-25 | Pyridine carboxamide |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0710844B2 (en) |
-
1985
- 1985-09-25 JP JP21182285A patent/JPH0710844B2/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6272668A (en) | 1987-04-03 |
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