SE436568B - Substituerad n-fenyl- eller n-naftyl-2-pyridinon-5-karboxylsyra och anvendning av denna for att reglera cerealieplantor - Google Patents
Substituerad n-fenyl- eller n-naftyl-2-pyridinon-5-karboxylsyra och anvendning av denna for att reglera cerealieplantorInfo
- Publication number
- SE436568B SE436568B SE7807006A SE7807006A SE436568B SE 436568 B SE436568 B SE 436568B SE 7807006 A SE7807006 A SE 7807006A SE 7807006 A SE7807006 A SE 7807006A SE 436568 B SE436568 B SE 436568B
- Authority
- SE
- Sweden
- Prior art keywords
- carboxy
- alkyl
- hydrogen
- substituted
- compounds
- Prior art date
Links
- 235000013339 cereals Nutrition 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims description 41
- -1 alkali metal salt Chemical class 0.000 claims description 17
- 239000000203 mixture Substances 0.000 claims description 13
- 150000003839 salts Chemical class 0.000 claims description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
- 125000005843 halogen group Chemical group 0.000 claims description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 230000012010 growth Effects 0.000 claims description 7
- 125000001424 substituent group Chemical group 0.000 claims description 7
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 7
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 6
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 6
- 229910052794 bromium Chemical group 0.000 claims description 6
- 239000000460 chlorine Substances 0.000 claims description 6
- 125000001624 naphthyl group Chemical group 0.000 claims description 6
- 230000001105 regulatory effect Effects 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 5
- 229910052801 chlorine Inorganic materials 0.000 claims description 5
- 229910052783 alkali metal Inorganic materials 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims description 4
- 230000000694 effects Effects 0.000 claims description 3
- 229910052736 halogen Chemical group 0.000 claims description 3
- 150000002367 halogens Chemical group 0.000 claims description 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 2
- 206010021929 Infertility male Diseases 0.000 claims description 2
- 208000007466 Male Infertility Diseases 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 7
- 239000001257 hydrogen Substances 0.000 claims 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 3
- 230000008635 plant growth Effects 0.000 claims 1
- 239000005648 plant growth regulator Substances 0.000 claims 1
- 125000003107 substituted aryl group Chemical group 0.000 claims 1
- 241000196324 Embryophyta Species 0.000 description 18
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- 238000002360 preparation method Methods 0.000 description 11
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 11
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 210000005069 ears Anatomy 0.000 description 7
- HZNVUJQVZSTENZ-UHFFFAOYSA-N 2,3-dichloro-5,6-dicyano-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(C#N)=C(C#N)C1=O HZNVUJQVZSTENZ-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 6
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 150000002148 esters Chemical class 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 239000010949 copper Substances 0.000 description 4
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 4
- 239000012442 inert solvent Substances 0.000 description 4
- 230000005764 inhibitory process Effects 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
- ZKQRVZYNOLPLQL-UHFFFAOYSA-N 1-(4-bromophenyl)-2,4-dimethyl-6-oxopyridine-3-carboxylic acid Chemical compound CC1=C(C(O)=O)C(C)=CC(=O)N1C1=CC=C(Br)C=C1 ZKQRVZYNOLPLQL-UHFFFAOYSA-N 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 239000003630 growth substance Substances 0.000 description 3
- 208000000509 infertility Diseases 0.000 description 3
- 230000036512 infertility Effects 0.000 description 3
- 208000021267 infertility disease Diseases 0.000 description 3
- LVWZTYCIRDMTEY-UHFFFAOYSA-N metamizole Chemical compound O=C1C(N(CS(O)(=O)=O)C)=C(C)N(C)N1C1=CC=CC=C1 LVWZTYCIRDMTEY-UHFFFAOYSA-N 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 239000002689 soil Substances 0.000 description 3
- 239000007921 spray Substances 0.000 description 3
- 230000017260 vegetative to reproductive phase transition of meristem Effects 0.000 description 3
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 2
- FZGAUIFQVKGSNJ-UHFFFAOYSA-N 1-(4-chlorophenyl)-2,4-dimethyl-6-oxopyridine-3-carboxylic acid Chemical compound CC1=C(C(O)=O)C(C)=CC(=O)N1C1=CC=C(Cl)C=C1 FZGAUIFQVKGSNJ-UHFFFAOYSA-N 0.000 description 2
- KJYBWQQRJURUAZ-UHFFFAOYSA-N 1-(4-chlorophenyl)-2-methyl-6-oxopyridine-3-carboxylic acid Chemical compound CC1=C(C(O)=O)C=CC(=O)N1C1=CC=C(Cl)C=C1 KJYBWQQRJURUAZ-UHFFFAOYSA-N 0.000 description 2
- WIQJNXWLZSPHLA-UHFFFAOYSA-N 1-(4-cyanophenyl)-2,4-dimethyl-6-oxopyridine-3-carboxylic acid Chemical compound CC1=C(C(O)=O)C(C)=CC(=O)N1C1=CC=C(C#N)C=C1 WIQJNXWLZSPHLA-UHFFFAOYSA-N 0.000 description 2
- ZPOODPZCZLCUAN-UHFFFAOYSA-N 3,4-dihydro-1h-pyridin-2-one Chemical compound O=C1CCC=CN1 ZPOODPZCZLCUAN-UHFFFAOYSA-N 0.000 description 2
- QSNSCYSYFYORTR-UHFFFAOYSA-N 4-chloroaniline Chemical compound NC1=CC=C(Cl)C=C1 QSNSCYSYFYORTR-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
- 239000005977 Ethylene Substances 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 240000007594 Oryza sativa Species 0.000 description 2
- 235000007164 Oryza sativa Nutrition 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 241000209140 Triticum Species 0.000 description 2
- 235000021307 Triticum Nutrition 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 125000003277 amino group Chemical class 0.000 description 2
- 150000001768 cations Chemical class 0.000 description 2
- 229940125904 compound 1 Drugs 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 230000018109 developmental process Effects 0.000 description 2
- 239000000428 dust Substances 0.000 description 2
- 230000000646 gametocidal effect Effects 0.000 description 2
- 239000002917 insecticide Substances 0.000 description 2
- 239000002198 insoluble material Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 2
- 125000003884 phenylalkyl group Chemical group 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 235000009566 rice Nutrition 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- UAOUIVVJBYDFKD-XKCDOFEDSA-N (1R,9R,10S,11R,12R,15S,18S,21R)-10,11,21-trihydroxy-8,8-dimethyl-14-methylidene-4-(prop-2-enylamino)-20-oxa-5-thia-3-azahexacyclo[9.7.2.112,15.01,9.02,6.012,18]henicosa-2(6),3-dien-13-one Chemical compound C([C@@H]1[C@@H](O)[C@@]23C(C1=C)=O)C[C@H]2[C@]12C(N=C(NCC=C)S4)=C4CC(C)(C)[C@H]1[C@H](O)[C@]3(O)OC2 UAOUIVVJBYDFKD-XKCDOFEDSA-N 0.000 description 1
- CJAAPVQEZPAQNI-UHFFFAOYSA-N (2-methylphenyl)methanamine Chemical compound CC1=CC=CC=C1CN CJAAPVQEZPAQNI-UHFFFAOYSA-N 0.000 description 1
- IWZSHWBGHQBIML-ZGGLMWTQSA-N (3S,8S,10R,13S,14S,17S)-17-isoquinolin-7-yl-N,N,10,13-tetramethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-amine Chemical compound CN(C)[C@H]1CC[C@]2(C)C3CC[C@@]4(C)[C@@H](CC[C@@H]4c4ccc5ccncc5c4)[C@@H]3CC=C2C1 IWZSHWBGHQBIML-ZGGLMWTQSA-N 0.000 description 1
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 description 1
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 description 1
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 description 1
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 description 1
- RHUYHJGZWVXEHW-UHFFFAOYSA-N 1,1-Dimethyhydrazine Chemical compound CN(C)N RHUYHJGZWVXEHW-UHFFFAOYSA-N 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- HBGOFPUKEWROBV-UHFFFAOYSA-N 1-(2-chloro-4-methylphenyl)-2,4-dimethyl-6-oxopyridine-3-carboxylic acid Chemical compound ClC1=CC(C)=CC=C1N1C(=O)C=C(C)C(C(O)=O)=C1C HBGOFPUKEWROBV-UHFFFAOYSA-N 0.000 description 1
- YYFAINZOXMNYSQ-UHFFFAOYSA-N 1-(2-chlorophenyl)-2,4-dimethyl-6-oxopyridine-3-carboxylic acid Chemical compound CC1=C(C(O)=O)C(C)=CC(=O)N1C1=CC=CC=C1Cl YYFAINZOXMNYSQ-UHFFFAOYSA-N 0.000 description 1
- IRLQNIUVLGLVER-UHFFFAOYSA-N 1-(2-fluorophenyl)-2,4-dimethyl-6-oxopyridine-3-carboxylic acid Chemical compound CC1=C(C(O)=O)C(C)=CC(=O)N1C1=CC=CC=C1F IRLQNIUVLGLVER-UHFFFAOYSA-N 0.000 description 1
- BDRPSADLSKXAAG-UHFFFAOYSA-N 1-(3,4-dichlorophenyl)-2,4-dimethyl-6-oxopyridine-3-carboxylic acid Chemical compound CC1=C(C(O)=O)C(C)=CC(=O)N1C1=CC=C(Cl)C(Cl)=C1 BDRPSADLSKXAAG-UHFFFAOYSA-N 0.000 description 1
- RTNRKGPPERCRDT-UHFFFAOYSA-N 1-(3,4-dichlorophenyl)-2-methyl-6-oxopyridine-3-carboxylic acid Chemical compound CC1=C(C(O)=O)C=CC(=O)N1C1=CC=C(Cl)C(Cl)=C1 RTNRKGPPERCRDT-UHFFFAOYSA-N 0.000 description 1
- XESZBAGJQATUSZ-UHFFFAOYSA-N 1-(3-chloro-4-methylphenyl)-2-methyl-6-oxopyridine-3-carboxylic acid Chemical compound C1=C(Cl)C(C)=CC=C1N1C(=O)C=CC(C(O)=O)=C1C XESZBAGJQATUSZ-UHFFFAOYSA-N 0.000 description 1
- ZJSNBAIYENCUGQ-UHFFFAOYSA-N 1-(3-chlorophenyl)-2,4-dimethyl-6-oxopyridine-3-carboxylic acid Chemical compound CC1=C(C(O)=O)C(C)=CC(=O)N1C1=CC=CC(Cl)=C1 ZJSNBAIYENCUGQ-UHFFFAOYSA-N 0.000 description 1
- NOSQFIIAOQZQRE-UHFFFAOYSA-N 1-(3-chlorophenyl)-5-fluoro-2,4-dimethyl-6-oxopyridine-3-carboxylic acid Chemical compound CC1=C(C(O)=O)C(C)=C(F)C(=O)N1C1=CC=CC(Cl)=C1 NOSQFIIAOQZQRE-UHFFFAOYSA-N 0.000 description 1
- FIIWHEHQLPKGEV-UHFFFAOYSA-N 1-(3-ethoxyphenyl)-2-methyl-6-oxopyridine-3-carboxylic acid Chemical compound CCOC1=CC=CC(N2C(C=CC(=C2C)C(O)=O)=O)=C1 FIIWHEHQLPKGEV-UHFFFAOYSA-N 0.000 description 1
- ZOUWMOOHHIFUGA-UHFFFAOYSA-N 1-(4-bromophenyl)-2,4-diethyl-6-oxopyridine-3-carboxylic acid Chemical compound CCC1=C(C(O)=O)C(CC)=CC(=O)N1C1=CC=C(Br)C=C1 ZOUWMOOHHIFUGA-UHFFFAOYSA-N 0.000 description 1
- UKQBFDLWZJTNOD-UHFFFAOYSA-N 1-(4-bromophenyl)-2-methyl-6-oxopyridine-3-carboxylic acid Chemical compound BrC1=CC=C(C=C1)N1C(C=CC(=C1C)C(=O)O)=O UKQBFDLWZJTNOD-UHFFFAOYSA-N 0.000 description 1
- FSIBTJPEDLGEFX-UHFFFAOYSA-N 1-(4-bromophenyl)-6-oxo-2,4-dipropylpyridine-3-carboxylic acid Chemical compound CCCC1=C(C(O)=O)C(CCC)=CC(=O)N1C1=CC=C(Br)C=C1 FSIBTJPEDLGEFX-UHFFFAOYSA-N 0.000 description 1
- FBSIDVMUZNTWGJ-UHFFFAOYSA-N 1-(4-bromophenyl)-6-oxo-2-propylpyridine-3-carboxylic acid Chemical compound CCCC1=C(C(O)=O)C=CC(=O)N1C1=CC=C(Br)C=C1 FBSIDVMUZNTWGJ-UHFFFAOYSA-N 0.000 description 1
- LPMXVJWKCXPXFI-UHFFFAOYSA-N 1-(4-chlorophenyl)-2,4,5-trimethyl-6-oxopyridine-3-carboxylic acid Chemical compound CC1=C(C(O)=O)C(C)=C(C)C(=O)N1C1=CC=C(Cl)C=C1 LPMXVJWKCXPXFI-UHFFFAOYSA-N 0.000 description 1
- ZADQNCLIOBLTBC-UHFFFAOYSA-N 1-(4-chlorophenyl)-2,4-diethyl-6-oxopyridine-3-carboxylic acid Chemical compound CCC1=C(C(O)=O)C(CC)=CC(=O)N1C1=CC=C(Cl)C=C1 ZADQNCLIOBLTBC-UHFFFAOYSA-N 0.000 description 1
- DXCOHECTXBBTIB-UHFFFAOYSA-N 1-(4-chlorophenyl)-2,5-dimethyl-6-oxopyridine-3-carboxylic acid Chemical compound O=C1C(C)=CC(C(O)=O)=C(C)N1C1=CC=C(Cl)C=C1 DXCOHECTXBBTIB-UHFFFAOYSA-N 0.000 description 1
- HAHJEUUYOUUAAQ-UHFFFAOYSA-N 1-(4-chlorophenyl)-4,6-dimethylpyridin-2-one Chemical compound ClC1=CC=C(C=C1)N1C(C=C(C=C1C)C)=O HAHJEUUYOUUAAQ-UHFFFAOYSA-N 0.000 description 1
- VUXWGUPNSHPKGW-UHFFFAOYSA-N 1-(4-chlorophenyl)-4-ethyl-2-methyl-6-oxopyridine-3-carboxylic acid Chemical compound CC1=C(C(O)=O)C(CC)=CC(=O)N1C1=CC=C(Cl)C=C1 VUXWGUPNSHPKGW-UHFFFAOYSA-N 0.000 description 1
- LODNHPWOYPVVCO-UHFFFAOYSA-N 1-(4-methoxyphenyl)-2,4-dimethyl-6-oxopyridine-3-carboxylic acid Chemical compound C1=CC(OC)=CC=C1N1C(=O)C=C(C)C(C(O)=O)=C1C LODNHPWOYPVVCO-UHFFFAOYSA-N 0.000 description 1
- BMVXCPBXGZKUPN-UHFFFAOYSA-N 1-hexanamine Chemical compound CCCCCCN BMVXCPBXGZKUPN-UHFFFAOYSA-N 0.000 description 1
- ZMZGFLUUZLELNE-UHFFFAOYSA-N 2,3,5-triiodobenzoic acid Chemical compound OC(=O)C1=CC(I)=CC(I)=C1I ZMZGFLUUZLELNE-UHFFFAOYSA-N 0.000 description 1
- LRGIIZXVSULULZ-UHFFFAOYSA-N 2,3-dichloro-2-methylpropanoic acid Chemical compound ClCC(Cl)(C)C(O)=O LRGIIZXVSULULZ-UHFFFAOYSA-N 0.000 description 1
- QIJIUJYANDSEKG-UHFFFAOYSA-N 2,4,4-trimethylpentan-2-amine Chemical compound CC(C)(C)CC(C)(C)N QIJIUJYANDSEKG-UHFFFAOYSA-N 0.000 description 1
- JEXUSJVYZVUWDS-UHFFFAOYSA-N 2,4-dimethyl-6-oxo-1-[4-(trifluoromethyl)phenyl]pyridine-3-carboxylic acid Chemical compound CC1=C(C(O)=O)C(C)=CC(=O)N1C1=CC=C(C(F)(F)F)C=C1 JEXUSJVYZVUWDS-UHFFFAOYSA-N 0.000 description 1
- KKCPYHSLHLGCTO-UHFFFAOYSA-N 2,5-dimethyl-6-oxo-1-[4-(trifluoromethyl)phenyl]pyridine-3-carboxylic acid Chemical compound O=C1C(C)=CC(C(O)=O)=C(C)N1C1=CC=C(C(F)(F)F)C=C1 KKCPYHSLHLGCTO-UHFFFAOYSA-N 0.000 description 1
- MJROZKLSHJICLS-UHFFFAOYSA-N 2-(2-ethylhexylamino)ethanol Chemical compound CCCCC(CC)CNCCO MJROZKLSHJICLS-UHFFFAOYSA-N 0.000 description 1
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- SMEAGLJLBFMCTN-UHFFFAOYSA-N 2-ethyl-4-methyl-6-oxo-1-[4-(trifluoromethyl)phenyl]pyridine-3-carboxylic acid Chemical compound CCC1=C(C(O)=O)C(C)=CC(=O)N1C1=CC=C(C(F)(F)F)C=C1 SMEAGLJLBFMCTN-UHFFFAOYSA-N 0.000 description 1
- ASUDFOJKTJLAIK-UHFFFAOYSA-N 2-methoxyethanamine Chemical compound COCCN ASUDFOJKTJLAIK-UHFFFAOYSA-N 0.000 description 1
- OWWHUWVLGQIGGN-UHFFFAOYSA-N 2-methyl-1-(4-methylphenyl)-6-oxopyridine-3-carboxylic acid Chemical compound C1=CC(C)=CC=C1N1C(=O)C=CC(C(O)=O)=C1C OWWHUWVLGQIGGN-UHFFFAOYSA-N 0.000 description 1
- CPJVTZWSFCDAGE-UHFFFAOYSA-N 2-methyl-1-(4-nitrophenyl)-6-oxopyridine-3-carboxylic acid Chemical compound CC1=C(C(O)=O)C=CC(=O)N1C1=CC=C([N+]([O-])=O)C=C1 CPJVTZWSFCDAGE-UHFFFAOYSA-N 0.000 description 1
- ZPSJGADGUYYRKE-UHFFFAOYSA-N 2H-pyran-2-one Chemical compound O=C1C=CC=CO1 ZPSJGADGUYYRKE-UHFFFAOYSA-N 0.000 description 1
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 description 1
- QBWKPGNFQQJGFY-QLFBSQMISA-N 3-[(1r)-1-[(2r,6s)-2,6-dimethylmorpholin-4-yl]ethyl]-n-[6-methyl-3-(1h-pyrazol-4-yl)imidazo[1,2-a]pyrazin-8-yl]-1,2-thiazol-5-amine Chemical compound N1([C@H](C)C2=NSC(NC=3C4=NC=C(N4C=C(C)N=3)C3=CNN=C3)=C2)C[C@H](C)O[C@H](C)C1 QBWKPGNFQQJGFY-QLFBSQMISA-N 0.000 description 1
- VUEZBQJWLDBIDE-UHFFFAOYSA-N 3-ethenyl-1,3-oxazolidin-2-one Chemical class C=CN1CCOC1=O VUEZBQJWLDBIDE-UHFFFAOYSA-N 0.000 description 1
- MPOYBFYHRQBZPM-UHFFFAOYSA-N 3h-pyridin-4-one Chemical class O=C1CC=NC=C1 MPOYBFYHRQBZPM-UHFFFAOYSA-N 0.000 description 1
- WDFQBORIUYODSI-UHFFFAOYSA-N 4-bromoaniline Chemical compound NC1=CC=C(Br)C=C1 WDFQBORIUYODSI-UHFFFAOYSA-N 0.000 description 1
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 description 1
- 125000006306 4-iodophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1I 0.000 description 1
- ODVBBZFQPGORMJ-UHFFFAOYSA-N 4-nitrobenzylamine Chemical compound NCC1=CC=C([N+]([O-])=O)C=C1 ODVBBZFQPGORMJ-UHFFFAOYSA-N 0.000 description 1
- 125000002373 5 membered heterocyclic group Chemical group 0.000 description 1
- MBIWZSAHEADABK-UHFFFAOYSA-N 5-bromo-2-methyl-6-oxo-1-[4-(trifluoromethyl)phenyl]pyridine-3-carboxylic acid Chemical compound CC1=C(C(O)=O)C=C(Br)C(=O)N1C1=CC=C(C(F)(F)F)C=C1 MBIWZSAHEADABK-UHFFFAOYSA-N 0.000 description 1
- LJMULVBVKHSJBM-UHFFFAOYSA-N 5-chloro-1-(2,4-dichlorophenyl)-2,4-dimethyl-6-oxopyridine-3-carboxylic acid Chemical compound CC1=C(C(O)=O)C(C)=C(Cl)C(=O)N1C1=CC=C(Cl)C=C1Cl LJMULVBVKHSJBM-UHFFFAOYSA-N 0.000 description 1
- 125000004070 6 membered heterocyclic group Chemical group 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 241001124076 Aphididae Species 0.000 description 1
- 229930192334 Auxin Natural products 0.000 description 1
- 244000075850 Avena orientalis Species 0.000 description 1
- 235000007319 Avena orientalis Nutrition 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- IVHVNMLJNASKHW-UHFFFAOYSA-M Chlorphonium chloride Chemical compound [Cl-].CCCC[P+](CCCC)(CCCC)CC1=CC=C(Cl)C=C1Cl IVHVNMLJNASKHW-UHFFFAOYSA-M 0.000 description 1
- 244000304337 Cuminum cyminum Species 0.000 description 1
- 235000007129 Cuminum cyminum Nutrition 0.000 description 1
- NOQGZXFMHARMLW-UHFFFAOYSA-N Daminozide Chemical compound CN(C)NC(=O)CCC(O)=O NOQGZXFMHARMLW-UHFFFAOYSA-N 0.000 description 1
- CWYNVVGOOAEACU-UHFFFAOYSA-N Fe2+ Chemical compound [Fe+2] CWYNVVGOOAEACU-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 229930191978 Gibberellin Natural products 0.000 description 1
- 240000005979 Hordeum vulgare Species 0.000 description 1
- 235000007340 Hordeum vulgare Nutrition 0.000 description 1
- 241000209510 Liliopsida Species 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- BGRDGMRNKXEXQD-UHFFFAOYSA-N Maleic hydrazide Chemical compound OC1=CC=C(O)N=N1 BGRDGMRNKXEXQD-UHFFFAOYSA-N 0.000 description 1
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 1
- BHHGXPLMPWCGHP-UHFFFAOYSA-N Phenethylamine Chemical compound NCCC1=CC=CC=C1 BHHGXPLMPWCGHP-UHFFFAOYSA-N 0.000 description 1
- NQRYJNQNLNOLGT-UHFFFAOYSA-O Piperidinium(1+) Chemical compound C1CC[NH2+]CC1 NQRYJNQNLNOLGT-UHFFFAOYSA-O 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 1
- WTKZEGDFNFYCGP-UHFFFAOYSA-O Pyrazolium Chemical compound C1=CN[NH+]=C1 WTKZEGDFNFYCGP-UHFFFAOYSA-O 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
- 240000006394 Sorghum bicolor Species 0.000 description 1
- 235000011684 Sorghum saccharatum Nutrition 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- 239000013504 Triton X-100 Substances 0.000 description 1
- 229920004890 Triton X-100 Polymers 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
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- HFBMWMNUJJDEQZ-UHFFFAOYSA-N acryloyl chloride Chemical compound ClC(=O)C=C HFBMWMNUJJDEQZ-UHFFFAOYSA-N 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 230000009418 agronomic effect Effects 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 125000006615 aromatic heterocyclic group Chemical group 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 239000002363 auxin Substances 0.000 description 1
- 239000003899 bactericide agent Substances 0.000 description 1
- 229910052788 barium Inorganic materials 0.000 description 1
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 239000003637 basic solution Substances 0.000 description 1
- YOUGRGFIHBUKRS-UHFFFAOYSA-N benzyl(trimethyl)azanium Chemical compound C[N+](C)(C)CC1=CC=CC=C1 YOUGRGFIHBUKRS-UHFFFAOYSA-N 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- OEVLWKCCNKIOTE-UHFFFAOYSA-N butyl 2,4-dimethyl-1-(3-methylphenyl)-6-oxopyridine-3-carboxylate Chemical compound CC1=C(C(=O)OCCCC)C(C)=CC(=O)N1C1=CC=CC(C)=C1 OEVLWKCCNKIOTE-UHFFFAOYSA-N 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- UHZZMRAGKVHANO-UHFFFAOYSA-M chlormequat chloride Chemical compound [Cl-].C[N+](C)(C)CCCl UHZZMRAGKVHANO-UHFFFAOYSA-M 0.000 description 1
- OEYIOHPDSNJKLS-UHFFFAOYSA-N choline Chemical compound C[N+](C)(C)CCO OEYIOHPDSNJKLS-UHFFFAOYSA-N 0.000 description 1
- 229960001231 choline Drugs 0.000 description 1
- 229940125846 compound 25 Drugs 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 239000004062 cytokinin Substances 0.000 description 1
- UQHKFADEQIVWID-UHFFFAOYSA-N cytokinin Natural products C1=NC=2C(NCC=C(CO)C)=NC=NC=2N1C1CC(O)C(CO)O1 UQHKFADEQIVWID-UHFFFAOYSA-N 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 239000012024 dehydrating agents Substances 0.000 description 1
- XBPCUCUWBYBCDP-UHFFFAOYSA-O dicyclohexylazanium Chemical compound C1CCCCC1[NH2+]C1CCCCC1 XBPCUCUWBYBCDP-UHFFFAOYSA-O 0.000 description 1
- RRBNGQHBEYUPFC-UHFFFAOYSA-N diethyl-(2-hydroxyethyl)-octylazanium Chemical compound CCCCCCCC[N+](CC)(CC)CCO RRBNGQHBEYUPFC-UHFFFAOYSA-N 0.000 description 1
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 239000004495 emulsifiable concentrate Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 150000002081 enamines Chemical class 0.000 description 1
- LQPNCNSDIQTYFE-UHFFFAOYSA-N ethyl 1-(4-chlorophenyl)-2,4-dimethyl-6-oxopyridine-3-carboxylate Chemical compound CC1=C(C(=O)OCC)C(C)=CC(=O)N1C1=CC=C(Cl)C=C1 LQPNCNSDIQTYFE-UHFFFAOYSA-N 0.000 description 1
- WJHKHVGBVRSUKL-UHFFFAOYSA-N ethyl 1-(4-fluorophenyl)-2,4-dimethyl-6-oxopyridine-3-carboxylate Chemical compound CC1=C(C(=O)OCC)C(C)=CC(=O)N1C1=CC=C(F)C=C1 WJHKHVGBVRSUKL-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000003337 fertilizer Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 239000003448 gibberellin Substances 0.000 description 1
- IXORZMNAPKEEDV-OBDJNFEBSA-N gibberellin A3 Chemical class C([C@@]1(O)C(=C)C[C@@]2(C1)[C@H]1C(O)=O)C[C@H]2[C@]2(C=C[C@@H]3O)[C@H]1[C@]3(C)C(=O)O2 IXORZMNAPKEEDV-OBDJNFEBSA-N 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 239000001963 growth medium Substances 0.000 description 1
- 125000001188 haloalkyl group Chemical group 0.000 description 1
- 230000002140 halogenating effect Effects 0.000 description 1
- 229910001385 heavy metal Inorganic materials 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 239000003864 humus Substances 0.000 description 1
- 238000009396 hybridization Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 210000003734 kidney Anatomy 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000035800 maturation Effects 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- 230000021121 meiosis Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- NURLYNIEJLLFAE-UHFFFAOYSA-N methyl 1-(4-chlorophenyl)-2,4-dimethyl-6-oxopyridine-3-carboxylate Chemical compound CC1=C(C(=O)OC)C(C)=CC(=O)N1C1=CC=C(Cl)C=C1 NURLYNIEJLLFAE-UHFFFAOYSA-N 0.000 description 1
- BJLDSCUCYCNDMQ-UHFFFAOYSA-N methyl 2-methyl-6-oxo-1-phenylpyridine-3-carboxylate Chemical compound CC1=C(C(=O)OC)C=CC(=O)N1C1=CC=CC=C1 BJLDSCUCYCNDMQ-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- YNAVUWVOSKDBBP-UHFFFAOYSA-O morpholinium Chemical compound [H+].C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-O 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 230000000885 phytotoxic effect Effects 0.000 description 1
- 125000004193 piperazinyl group Chemical group 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- JKANAVGODYYCQF-UHFFFAOYSA-N prop-2-yn-1-amine Chemical compound NCC#C JKANAVGODYYCQF-UHFFFAOYSA-N 0.000 description 1
- UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical class OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 230000005070 ripening Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 229910052712 strontium Inorganic materials 0.000 description 1
- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- NBNBICNWNFQDDD-UHFFFAOYSA-N sulfuryl dibromide Chemical compound BrS(Br)(=O)=O NBNBICNWNFQDDD-UHFFFAOYSA-N 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- GCRCSLNXFKCFHB-UHFFFAOYSA-N triethyl(hexyl)azanium Chemical compound CCCCCC[N+](CC)(CC)CC GCRCSLNXFKCFHB-UHFFFAOYSA-N 0.000 description 1
- ZMANZCXQSJIPKH-UHFFFAOYSA-O triethylammonium ion Chemical compound CC[NH+](CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-O 0.000 description 1
- WSFDRHZUAHDHDN-UHFFFAOYSA-N trimethyl-[(4-methylphenyl)methyl]azanium Chemical compound CC1=CC=C(C[N+](C)(C)C)C=C1 WSFDRHZUAHDHDN-UHFFFAOYSA-N 0.000 description 1
- PJGBDAXHQYTCOA-UHFFFAOYSA-N tris[2-(dimethylamino)ethyl] phosphate Chemical compound CN(C)CCOP(=O)(OCCN(C)C)OCCN(C)C PJGBDAXHQYTCOA-UHFFFAOYSA-N 0.000 description 1
- 230000009105 vegetative growth Effects 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- JLYXXMFPNIAWKQ-UHFFFAOYSA-N γ Benzene hexachloride Chemical compound ClC1C(Cl)C(Cl)C(Cl)C(Cl)C1Cl JLYXXMFPNIAWKQ-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/79—Acids; Esters
- C07D213/80—Acids; Esters in position 3
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/80—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D211/84—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen directly attached to ring carbon atoms
- C07D211/90—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Plant Pathology (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Pyridine Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US81605177A | 1977-07-15 | 1977-07-15 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| SE7807006L SE7807006L (sv) | 1979-01-16 |
| SE436568B true SE436568B (sv) | 1985-01-07 |
Family
ID=25219570
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SE7807006A SE436568B (sv) | 1977-07-15 | 1978-06-19 | Substituerad n-fenyl- eller n-naftyl-2-pyridinon-5-karboxylsyra och anvendning av denna for att reglera cerealieplantor |
Country Status (17)
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4714492A (en) * | 1980-05-12 | 1987-12-22 | Rohm And Haas Company | Certain 2-phenyl-4-oxo-nicotinates and their use for inducing male sterility in a cereal grain plant |
| US4936904A (en) * | 1980-05-12 | 1990-06-26 | Carlson Glenn R | Aryl-4-oxonicotinates useful for inducing male sterility in cereal grain plants |
| US4568751A (en) * | 1983-04-29 | 1986-02-04 | Merrell Dow Pharmaceuticals Inc. | 5-Acyl-2-(1H)-pyridinones |
| AU2001278491A1 (en) * | 2000-07-18 | 2002-01-30 | Basf Aktiengesellschaft | 1-aryl-4-alkyl halide-2(1h)-pyridones and their use as herbicides |
| US7728013B2 (en) * | 2005-05-10 | 2010-06-01 | Intermune, Inc. | Method of modulating stress-activated protein kinase system |
| CA3034994A1 (en) | 2008-06-03 | 2009-12-10 | Intermune, Inc. | Substituted aryl-2 pyridone compounds and use thereof for treating inflammatory and fibrotic disorders |
| AR092742A1 (es) | 2012-10-02 | 2015-04-29 | Intermune Inc | Piridinonas antifibroticas |
| CA2943363A1 (en) | 2014-04-02 | 2015-10-08 | Intermune, Inc. | Anti-fibrotic pyridinones |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1316461A (fr) * | 1959-09-23 | 1963-02-01 | Wallace & Tiernan Inc | Perfectionnements apportés aux procédés pour la préparation de dérivés de la 2-pyridone |
-
1978
- 1978-05-26 GB GB23085/78A patent/GB1596887A/en not_active Expired
- 1978-06-19 SE SE7807006A patent/SE436568B/sv not_active IP Right Cessation
- 1978-06-30 NZ NZ187735A patent/NZ187735A/xx unknown
- 1978-07-04 AR AR272835A patent/AR218070A1/es active
- 1978-07-04 CA CA306,765A patent/CA1085857A/en not_active Expired
- 1978-07-11 NL NLAANVRAGE7807464,A patent/NL188695C/xx not_active IP Right Cessation
- 1978-07-12 FR FR7820803A patent/FR2397405A1/fr active Granted
- 1978-07-12 DE DE19782830700 patent/DE2830700A1/de active Granted
- 1978-07-13 AU AU38025/78A patent/AU521772B2/en not_active Expired
- 1978-07-13 IL IL55133A patent/IL55133A/xx unknown
- 1978-07-13 CH CH761678A patent/CH635324A5/fr not_active IP Right Cessation
- 1978-07-14 BE BE189285A patent/BE868999A/xx not_active IP Right Cessation
- 1978-07-14 DK DK318578A patent/DK158350C/da not_active IP Right Cessation
- 1978-07-14 HU HU78RO989A patent/HU181943B/hu unknown
- 1978-07-14 IT IT68682/78A patent/IT1108115B/it active
- 1978-07-14 JP JP8599978A patent/JPS5452084A/ja active Pending
- 1978-07-15 ES ES471780A patent/ES471780A1/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| NL188695C (nl) | 1992-09-01 |
| SE7807006L (sv) | 1979-01-16 |
| CH635324A5 (en) | 1983-03-31 |
| AU3802578A (en) | 1980-01-17 |
| HU181943B (en) | 1983-11-28 |
| FR2397405A1 (fr) | 1979-02-09 |
| AR218070A1 (es) | 1980-05-15 |
| IT7868682A0 (it) | 1978-07-14 |
| DK318578A (da) | 1979-01-16 |
| ES471780A1 (es) | 1979-01-16 |
| DE2830700C2 (enrdf_load_stackoverflow) | 1989-03-16 |
| NL7807464A (nl) | 1979-01-17 |
| BE868999A (fr) | 1979-01-15 |
| CA1085857A (en) | 1980-09-16 |
| IL55133A0 (en) | 1978-09-29 |
| DE2830700A1 (de) | 1979-02-01 |
| IT1108115B (it) | 1985-12-02 |
| IL55133A (en) | 1982-11-30 |
| NL188695B (nl) | 1992-04-01 |
| FR2397405B1 (enrdf_load_stackoverflow) | 1981-12-24 |
| DK158350B (da) | 1990-05-07 |
| NZ187735A (en) | 1981-03-16 |
| JPS5452084A (en) | 1979-04-24 |
| DK158350C (da) | 1990-10-08 |
| GB1596887A (en) | 1981-09-03 |
| AU521772B2 (en) | 1982-04-29 |
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