JPS6365068B2 - - Google Patents
Info
- Publication number
- JPS6365068B2 JPS6365068B2 JP10225781A JP10225781A JPS6365068B2 JP S6365068 B2 JPS6365068 B2 JP S6365068B2 JP 10225781 A JP10225781 A JP 10225781A JP 10225781 A JP10225781 A JP 10225781A JP S6365068 B2 JPS6365068 B2 JP S6365068B2
- Authority
- JP
- Japan
- Prior art keywords
- formula
- isonicotinic acid
- general formula
- lower alkyl
- alkyl group
- 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
Links
- 238000004519 manufacturing process Methods 0.000 claims description 13
- -1 Isonicotinic acid halide Chemical class 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
- 125000005843 halogen group Chemical group 0.000 claims description 7
- WGGVDOFTTMYSRV-UHFFFAOYSA-N n-(4-acetylphenyl)pyridine-4-carboxamide Chemical compound C1=CC(C(=O)C)=CC=C1NC(=O)C1=CC=NC=C1 WGGVDOFTTMYSRV-UHFFFAOYSA-N 0.000 claims description 6
- FCTZHFATVFONMW-UHFFFAOYSA-N n-phenylpyridine-4-carboxamide Chemical class C=1C=NC=CC=1C(=O)NC1=CC=CC=C1 FCTZHFATVFONMW-UHFFFAOYSA-N 0.000 claims description 4
- 239000005648 plant growth regulator Substances 0.000 claims description 4
- 150000003931 anilides Chemical class 0.000 claims description 3
- TWBYWOBDOCUKOW-UHFFFAOYSA-N isonicotinic acid Natural products OC(=O)C1=CC=NC=C1 TWBYWOBDOCUKOW-UHFFFAOYSA-N 0.000 claims description 3
- 239000004480 active ingredient Substances 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 description 23
- 241000209094 Oryza Species 0.000 description 14
- 235000007164 Oryza sativa Nutrition 0.000 description 14
- 235000009566 rice Nutrition 0.000 description 14
- 238000012360 testing method Methods 0.000 description 7
- 241000196324 Embryophyta Species 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 240000008067 Cucumis sativus Species 0.000 description 5
- 235000010799 Cucumis sativus var sativus Nutrition 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 230000012010 growth Effects 0.000 description 5
- 241000209504 Poaceae Species 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 238000003306 harvesting Methods 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 4
- 239000002689 soil Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 229940079593 drug Drugs 0.000 description 3
- 238000000921 elemental analysis Methods 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- HEQOJEGTZCTHCF-UHFFFAOYSA-N 2-amino-1-phenylethanone Chemical compound NCC(=O)C1=CC=CC=C1 HEQOJEGTZCTHCF-UHFFFAOYSA-N 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 2
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 125000005037 alkyl phenyl group Chemical group 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 239000003638 chemical reducing agent Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 239000012046 mixed solvent Substances 0.000 description 2
- 230000008635 plant growth Effects 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 230000001105 regulatory effect Effects 0.000 description 2
- 239000012279 sodium borohydride Substances 0.000 description 2
- 229910000033 sodium borohydride Inorganic materials 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- 244000025254 Cannabis sativa Species 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 240000000111 Saccharum officinarum Species 0.000 description 1
- 235000007201 Saccharum officinarum Nutrition 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 244000061458 Solanum melongena Species 0.000 description 1
- 235000002597 Solanum melongena Nutrition 0.000 description 1
- 235000021307 Triticum Nutrition 0.000 description 1
- 244000098338 Triticum aestivum Species 0.000 description 1
- 241000607479 Yersinia pestis Species 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 239000003905 agrochemical Substances 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
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000012752 auxiliary agent Substances 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
- 239000011230 binding agent Substances 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 150000001720 carbohydrates Chemical class 0.000 description 1
- 229930002875 chlorophyll Natural products 0.000 description 1
- 235000019804 chlorophyll Nutrition 0.000 description 1
- ATNHDLDRLWWWCB-AENOIHSZSA-M chlorophyll a Chemical compound C1([C@@H](C(=O)OC)C(=O)C2=C3C)=C2N2C3=CC(C(CC)=C3C)=[N+]4C3=CC3=C(C=C)C(C)=C5N3[Mg-2]42[N+]2=C1[C@@H](CCC(=O)OC\C=C(/C)CCC[C@H](C)CCC[C@H](C)CCCC(C)C)[C@H](C)C2=C5 ATNHDLDRLWWWCB-AENOIHSZSA-M 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- YDEXUEFDPVHGHE-GGMCWBHBSA-L disodium;(2r)-3-(2-hydroxy-3-methoxyphenyl)-2-[2-methoxy-4-(3-sulfonatopropyl)phenoxy]propane-1-sulfonate Chemical compound [Na+].[Na+].COC1=CC=CC(C[C@H](CS([O-])(=O)=O)OC=2C(=CC(CCCS([O-])(=O)=O)=CC=2)OC)=C1O YDEXUEFDPVHGHE-GGMCWBHBSA-L 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000003337 fertilizer Substances 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 230000000887 hydrating effect Effects 0.000 description 1
- BNTRVUUJBGBGLZ-UHFFFAOYSA-N hydron;pyridine-4-carbonyl chloride;chloride Chemical compound Cl.ClC(=O)C1=CC=NC=C1 BNTRVUUJBGBGLZ-UHFFFAOYSA-N 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000012280 lithium aluminium hydride Substances 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- DUCFDYVKLQHHOW-UHFFFAOYSA-N n-(2-acetylphenyl)pyridine-4-carboxamide Chemical compound CC(=O)C1=CC=CC=C1NC(=O)C1=CC=NC=C1 DUCFDYVKLQHHOW-UHFFFAOYSA-N 0.000 description 1
- 230000029553 photosynthesis Effects 0.000 description 1
- 238000010672 photosynthesis Methods 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- 235000011118 potassium hydroxide Nutrition 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000002786 root growth Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000009331 sowing Methods 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000002054 transplantation Methods 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Landscapes
- Pyridine Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Priority Applications (10)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP10225781A JPS584767A (ja) | 1981-07-02 | 1981-07-02 | イソニコチン酸アニリド誘導体，その製造法およびその化合物からなる植物生長調節剤 |
| AR286942A AR230049A1 (es) | 1980-09-30 | 1981-08-30 | Derivados de isonicotinanilida,proceso para su preparacion y composicion reguladora del crecimiento de las plantas conteniendo los mismos |
| US06/306,582 US4377407A (en) | 1980-09-30 | 1981-09-28 | Isonicotinanilide derivatives, plant growth regulating compositions and use |
| KR1019810003647A KR870001943B1 (ko) | 1980-09-30 | 1981-09-29 | 이소 니코틴 산 아닐리드 유도체의 제조방법 |
| AU75766/81A AU544907B2 (en) | 1980-09-30 | 1981-09-29 | Isonicotinanilide derivatives |
| EP81107793A EP0048998B1 (fr) | 1980-09-30 | 1981-09-30 | Dérivés d'isonicotinanilides, leur procédé de préparation et leur application comme régulateurs de la croissance de plantes |
| DE8181107793T DE3168175D1 (en) | 1980-09-30 | 1981-09-30 | Isonicotinanilide derivatives, process for preparing the same and plant growth regulator containing the same |
| BR8106298A BR8106298A (pt) | 1980-09-30 | 1981-09-30 | Composto processo para sua preparacao e composicao reguladora de crescimento de planta |
| CA000387016A CA1167855A (fr) | 1980-09-30 | 1981-09-30 | Procede d'obtention de derives d'isonicotinanilide et regulateur de la croissance vegetale qui contient des dits produits |
| ES505920A ES8301924A1 (es) | 1980-09-30 | 1981-09-30 | Un procedimiento para la preparacion de derivados de isonicotinanilida. |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP10225781A JPS584767A (ja) | 1981-07-02 | 1981-07-02 | イソニコチン酸アニリド誘導体，その製造法およびその化合物からなる植物生長調節剤 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS584767A JPS584767A (ja) | 1983-01-11 |
| JPS6365068B2 true JPS6365068B2 (fr) | 1988-12-14 |
Family
ID=14322532
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP10225781A Granted JPS584767A (ja) | 1980-09-30 | 1981-07-02 | イソニコチン酸アニリド誘導体，その製造法およびその化合物からなる植物生長調節剤 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS584767A (fr) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS59122469A (ja) * | 1982-12-29 | 1984-07-14 | Chugai Pharmaceut Co Ltd | イソニコチン酸アニリド誘導体、その製造法およびその化合物からなる植物生長調節剤 |
| JPS6197726U (fr) * | 1984-12-03 | 1986-06-23 |
-
1981
- 1981-07-02 JP JP10225781A patent/JPS584767A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS584767A (ja) | 1983-01-11 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JPS6141485B2 (fr) | ||
| JPS5815962A (ja) | 新規スルホニルウレイド誘導体 | |
| US4377407A (en) | Isonicotinanilide derivatives, plant growth regulating compositions and use | |
| JPS6365068B2 (fr) | ||
| JPS59122402A (ja) | イソニコチン酸アニリド誘導体よりなる植物生長調節用組成物および植物の生長調節方法 | |
| JPH0217546B2 (fr) | ||
| JPS6341393B2 (fr) | ||
| JP2516345B2 (ja) | イミダゾ−ル誘導体 | |
| JPH0329070B2 (fr) | ||
| JPS6054954B2 (ja) | ジフエニルエ−テル誘導体，およびジフエニルエ−テル誘導体を含有する除草剤 | |
| JPS6011031B2 (ja) | イミダゾ−ル誘導体の製造方法 | |
| JPH0322361B2 (fr) | ||
| KR830001714B1 (ko) | 디페닐 에테르 유도체의 제조방법 | |
| JPS61221170A (ja) | トリフルオロメタンスルホニルアミド誘導体及びそれを有効成分とする除草剤 | |
| JPH0244307B2 (ja) | Isonikochinsananiridojudotai*sonoseizohooyobisonokagobutsukaranarushokubutsuseichochosetsuzai | |
| JP3066536B2 (ja) | 縮合ヘテロ環誘導体及び除草剤 | |
| JPS60136565A (ja) | アセタ−ル類化合物、その製造法およびそれらを含有する農園芸用殺菌剤 | |
| JPS59122472A (ja) | ピラゾ−ル誘導体、その製造方法および該誘導体を含有する選択性除草剤 | |
| JPS606661A (ja) | Ｎ−フエニルイタコン酸イミド誘導体及び農園芸用殺菌剤 | |
| JPS6058917B2 (ja) | チオフエン誘導体および農園芸用殺菌剤 | |
| JPS6230744A (ja) | シクロヘキサン誘導体、及び植物生長調節剤 | |
| JPH03284685A (ja) | テトラハイドロピリダジノチアジアゾール誘導体及び除草剤 | |
| JPS59118769A (ja) | Ｎ−（１−置換−２，２，２−トリクロルエチル）−ホルムアミド誘導体および農園芸用殺虫剤 | |
| JPS60255765A (ja) | ピロ−ル誘導体、製造法及びそれらを含む除草及び殺菌剤 | |
| JPH0353282B2 (fr) |