NZ197027A - 4-oxo-2-phenyl-nicotinic acids salts and esters and growth regulating compositions - Google Patents
4-oxo-2-phenyl-nicotinic acids salts and esters and growth regulating compositionsInfo
- Publication number
- NZ197027A NZ197027A NZ197027A NZ19702781A NZ197027A NZ 197027 A NZ197027 A NZ 197027A NZ 197027 A NZ197027 A NZ 197027A NZ 19702781 A NZ19702781 A NZ 19702781A NZ 197027 A NZ197027 A NZ 197027A
- Authority
- NZ
- New Zealand
- Prior art keywords
- compound
- alkyl
- methyl
- hydrogen
- compounds
- Prior art date
Links
- 230000001105 regulatory effect Effects 0.000 title claims abstract description 16
- 239000000203 mixture Substances 0.000 title claims description 37
- 230000012010 growth Effects 0.000 title claims description 10
- 150000002148 esters Chemical class 0.000 title description 7
- DSWRYEHXHBAWFW-UHFFFAOYSA-N 4-oxo-2-phenyl-3H-pyridine-3-carboxylic acid Chemical class OC(=O)C1C(=O)C=CN=C1C1=CC=CC=C1 DSWRYEHXHBAWFW-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 129
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 70
- 150000003839 salts Chemical class 0.000 claims abstract description 44
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 35
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 34
- 239000002253 acid Substances 0.000 claims abstract description 32
- 239000001257 hydrogen Substances 0.000 claims abstract description 30
- -1 hydroxy, carboxy, carboxy salt Chemical group 0.000 claims abstract description 21
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 11
- 150000002367 halogens Chemical class 0.000 claims abstract description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 7
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 5
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 5
- 125000001424 substituent group Chemical group 0.000 claims abstract description 4
- 125000004953 trihalomethyl group Chemical group 0.000 claims abstract description 3
- 239000011734 sodium Substances 0.000 claims description 42
- 241000196324 Embryophyta Species 0.000 claims description 35
- 206010021929 Infertility male Diseases 0.000 claims description 29
- 208000007466 Male Infertility Diseases 0.000 claims description 29
- 125000000217 alkyl group Chemical group 0.000 claims description 29
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 29
- 230000035558 fertility Effects 0.000 claims description 22
- 238000000034 method Methods 0.000 claims description 18
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 14
- 239000003795 chemical substances by application Substances 0.000 claims description 14
- 240000008042 Zea mays Species 0.000 claims description 12
- 235000002017 Zea mays subsp mays Nutrition 0.000 claims description 12
- 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 claims description 11
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 10
- 235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 claims description 9
- 150000002431 hydrogen Chemical class 0.000 claims description 9
- 235000009973 maize Nutrition 0.000 claims description 9
- 229910052708 sodium Inorganic materials 0.000 claims description 9
- 235000007340 Hordeum vulgare Nutrition 0.000 claims description 8
- 235000011684 Sorghum saccharatum Nutrition 0.000 claims description 8
- 235000021307 Triticum Nutrition 0.000 claims description 8
- 239000004094 surface-active agent Substances 0.000 claims description 7
- 240000006394 Sorghum bicolor Species 0.000 claims description 6
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 6
- 239000000460 chlorine Substances 0.000 claims description 6
- 229910052801 chlorine Inorganic materials 0.000 claims description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 5
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 5
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 5
- 229910052794 bromium Inorganic materials 0.000 claims description 5
- 239000011737 fluorine Chemical group 0.000 claims description 5
- 229910052731 fluorine Chemical group 0.000 claims description 5
- 239000011591 potassium Substances 0.000 claims description 5
- 229910052700 potassium Inorganic materials 0.000 claims description 5
- 239000004480 active ingredient Substances 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 244000038559 crop plants Species 0.000 claims description 4
- 239000004459 forage Substances 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 2
- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- 150000001340 alkali metals Chemical class 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 240000005979 Hordeum vulgare Species 0.000 claims 1
- 244000098338 Triticum aestivum Species 0.000 claims 1
- 230000008635 plant growth Effects 0.000 abstract description 5
- 235000013339 cereals Nutrition 0.000 abstract description 4
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 5
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 abstract 1
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 54
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 54
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 40
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 30
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 22
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- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 13
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 11
- 230000000694 effects Effects 0.000 description 11
- 238000012360 testing method Methods 0.000 description 11
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- 238000009396 hybridization Methods 0.000 description 10
- 230000005764 inhibitory process Effects 0.000 description 10
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
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- 229910052757 nitrogen Inorganic materials 0.000 description 8
- 241000209219 Hordeum Species 0.000 description 7
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 7
- 238000003760 magnetic stirring Methods 0.000 description 7
- 239000005648 plant growth regulator Substances 0.000 description 7
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- 150000007513 acids Chemical class 0.000 description 6
- 238000001914 filtration Methods 0.000 description 6
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 6
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 6
- 239000002244 precipitate Substances 0.000 description 6
- 229960000583 acetic acid Drugs 0.000 description 5
- 125000004429 atom Chemical group 0.000 description 5
- 239000012141 concentrate Substances 0.000 description 5
- 239000000463 material Substances 0.000 description 5
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- 238000003756 stirring Methods 0.000 description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 4
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 4
- 240000007594 Oryza sativa Species 0.000 description 4
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- 239000002671 adjuvant Substances 0.000 description 4
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- 238000011282 treatment Methods 0.000 description 4
- PCUDMVUZJHCVFO-UHFFFAOYSA-N 1,6-dimethyl-4-oxo-2-phenylpyridine-3-carboxylic acid Chemical compound CN1C(C)=CC(=O)C(C(O)=O)=C1C1=CC=CC=C1 PCUDMVUZJHCVFO-UHFFFAOYSA-N 0.000 description 3
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- NPYPAHLBTDXSSS-UHFFFAOYSA-N Potassium ion Chemical compound [K+] NPYPAHLBTDXSSS-UHFFFAOYSA-N 0.000 description 3
- 235000007238 Secale cereale Nutrition 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 235000019714 Triticale Nutrition 0.000 description 3
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 3
- OCBFFGCSTGGPSQ-UHFFFAOYSA-N [CH2]CC Chemical compound [CH2]CC OCBFFGCSTGGPSQ-UHFFFAOYSA-N 0.000 description 3
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- 230000000844 anti-bacterial effect Effects 0.000 description 3
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- DEDLAMTXOLUIPK-UHFFFAOYSA-N ethyl 3-(methylamino)-3-phenylprop-2-enoate Chemical compound CCOC(=O)C=C(NC)C1=CC=CC=C1 DEDLAMTXOLUIPK-UHFFFAOYSA-N 0.000 description 3
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- JVYKPOBJQGSVDJ-UHFFFAOYSA-N methyl 2-(4-chlorophenyl)-6-methyl-4-oxopyran-3-carboxylate Chemical compound O1C(C)=CC(=O)C(C(=O)OC)=C1C1=CC=C(Cl)C=C1 JVYKPOBJQGSVDJ-UHFFFAOYSA-N 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
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- SZUVGFMDDVSKSI-WIFOCOSTSA-N (1s,2s,3s,5r)-1-(carboxymethyl)-3,5-bis[(4-phenoxyphenyl)methyl-propylcarbamoyl]cyclopentane-1,2-dicarboxylic acid Chemical compound O=C([C@@H]1[C@@H]([C@](CC(O)=O)([C@H](C(=O)N(CCC)CC=2C=CC(OC=3C=CC=CC=3)=CC=2)C1)C(O)=O)C(O)=O)N(CCC)CC(C=C1)=CC=C1OC1=CC=CC=C1 SZUVGFMDDVSKSI-WIFOCOSTSA-N 0.000 description 2
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- 239000010452 phosphate Substances 0.000 description 1
- 239000010665 pine oil Substances 0.000 description 1
- 230000010152 pollination Effects 0.000 description 1
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 1
- 239000000244 polyoxyethylene sorbitan monooleate Substances 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229920000053 polysorbate 80 Polymers 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical class OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000002516 radical scavenger Substances 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 230000008707 rearrangement Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 238000002791 soaking Methods 0.000 description 1
- 235000019265 sodium DL-malate Nutrition 0.000 description 1
- 239000001394 sodium malate Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- RPACBEVZENYWOL-XFULWGLBSA-M sodium;(2r)-2-[6-(4-chlorophenoxy)hexyl]oxirane-2-carboxylate Chemical compound [Na+].C=1C=C(Cl)C=CC=1OCCCCCC[C@]1(C(=O)[O-])CO1 RPACBEVZENYWOL-XFULWGLBSA-M 0.000 description 1
- PKCJUDAYCIACTM-UHFFFAOYSA-M sodium;1,6-dimethyl-4-oxo-2-phenylpyridine-3-carboxylate Chemical compound [Na+].CN1C(C)=CC(=O)C(C([O-])=O)=C1C1=CC=CC=C1 PKCJUDAYCIACTM-UHFFFAOYSA-M 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000003892 spreading Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 229910052712 strontium Inorganic materials 0.000 description 1
- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical group [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- GPRLSGONYQIRFK-MNYXATJNSA-N triton Chemical compound [3H+] GPRLSGONYQIRFK-MNYXATJNSA-N 0.000 description 1
- 230000009105 vegetative growth Effects 0.000 description 1
- 230000017260 vegetative to reproductive phase transition of meristem Effects 0.000 description 1
- 239000010455 vermiculite Substances 0.000 description 1
- 229910052902 vermiculite Inorganic materials 0.000 description 1
- 235000019354 vermiculite Nutrition 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
- 238000009736 wetting Methods 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
- A01H—NEW PLANTS OR NON-TRANSGENIC PROCESSES FOR OBTAINING THEM; PLANT REPRODUCTION BY TISSUE CULTURE TECHNIQUES
- A01H1/00—Processes for modifying genotypes ; Plants characterised by associated natural traits
- A01H1/02—Methods or apparatus for hybridisation; Artificial pollination ; Fertility
- A01H1/026—Methods or apparatus for hybridisation; Artificial pollination ; Fertility by treatment with chemicals
-
- 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
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/34—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D309/36—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with oxygen atoms directly attached to ring carbon atoms
- C07D309/38—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with oxygen atoms directly attached to ring carbon atoms one oxygen atom in position 2 or 4, e.g. pyrones
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Environmental Sciences (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Developmental Biology & Embryology (AREA)
- Botany (AREA)
- Genetics & Genomics (AREA)
- Zoology (AREA)
- Agronomy & Crop Science (AREA)
- Engineering & Computer Science (AREA)
- Pest Control & Pesticides (AREA)
- Wood Science & Technology (AREA)
- Plant Pathology (AREA)
- Dentistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Pyridine Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Breeding Of Plants And Reproduction By Means Of Culturing (AREA)
- Pyrane Compounds (AREA)
- Catalysts (AREA)
- Silicon Polymers (AREA)
- Cultivation Of Plants (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US14807980A | 1980-05-12 | 1980-05-12 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NZ197027A true NZ197027A (en) | 1984-03-16 |
Family
ID=22524172
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NZ197027A NZ197027A (en) | 1980-05-12 | 1981-05-07 | 4-oxo-2-phenyl-nicotinic acids salts and esters and growth regulating compositions |
Country Status (10)
Families Citing this family (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1236700A (en) * | 1983-04-26 | 1988-05-17 | Samuel E. Sherba | Haploid and doubled haploid angiosperms |
| GB2185018B (en) * | 1985-12-27 | 1989-11-29 | Daicel Chem | Pyridine-3-carboxamide derivatives and their use as plant growth regulates |
| US4780123A (en) * | 1986-06-09 | 1988-10-25 | Stauffer Chemical Company | Certain 4-oxo-3-benzoylvalerolactones and thiolactones |
| US4808720A (en) * | 1986-06-09 | 1989-02-28 | Stauffer Chemical Company | Certain 3-benzoyl-4-oxolactams |
| US4808733A (en) * | 1986-06-09 | 1989-02-28 | Stauffer Chemical Company | Certain 4-oxo-3-benzoylvalerolactones and thiolactones |
| AU590971B2 (en) * | 1986-09-19 | 1989-11-23 | Australian Wool Corporation | Depilating process |
| GB8824144D0 (en) * | 1988-10-14 | 1988-11-23 | Ici Plc | Substituted oxonicotinates & their use as chemical hybridisation agents on dicotyledonous plants |
| FR2687674B1 (fr) * | 1992-02-07 | 1995-05-19 | Roussel Uclaf | Nouveaux derives de la pyridone, leur procede de preparation, les nouveaux intermediaires obtenus, leur application a titre de medicaments et les compositions pharmaceutiques les renfermant. |
| GB202018994D0 (en) * | 2020-12-02 | 2021-01-13 | Syngenta Crop Protection Ag | Herbicidal derivatives |
| GB202018996D0 (en) | 2020-12-02 | 2021-01-13 | Syngenta Crop Protection Ag | Herbicidal derivatives |
| WO2023110664A1 (en) | 2021-12-17 | 2023-06-22 | Syngenta Crop Protection Ag | Herbicidal pyridone derivatives |
| CN119095827A (zh) | 2022-04-27 | 2024-12-06 | 先正达农作物保护股份公司 | 除草2-氧代-烟酸衍生物 |
| WO2023232673A1 (en) | 2022-06-01 | 2023-12-07 | Syngenta Crop Protection Ag | Herbicidal derivatives |
| AU2023280572A1 (en) | 2022-06-01 | 2024-12-05 | Syngenta Crop Protection Ag | Herbicidal derivatives |
| KR20250019694A (ko) | 2022-06-01 | 2025-02-10 | 신젠타 크롭 프로텍션 아게 | 제초제 유도체 |
| AR130324A1 (es) | 2022-09-01 | 2024-11-27 | Syngenta Crop Protection Ag | Derivados herbicidas |
| AU2023406528A1 (en) | 2022-12-01 | 2025-05-22 | Syngenta Crop Protection Ag | Herbicidal derivatives |
| AR132501A1 (es) | 2023-04-27 | 2025-07-02 | Syngenta Crop Protection Ag | Derivados herbicidas |
| WO2025087845A1 (en) | 2023-10-23 | 2025-05-01 | Syngenta Crop Protection Ag | Herbicidal derivatives |
| WO2025108824A1 (en) | 2023-11-21 | 2025-05-30 | Syngenta Crop Protection Ag | Herbicidal derivatives |
| WO2025119663A1 (en) | 2023-12-05 | 2025-06-12 | Syngenta Crop Protection Ag | Herbicidal derivatives |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4028084A (en) * | 1974-10-11 | 1977-06-07 | Rohm And Haas Company | Derivatives of 3-carboxy pyrid-2-ones |
| AT362613B (de) * | 1975-08-27 | 1981-06-10 | Lilly Co Eli | Herbizides mittel |
| US4115101A (en) * | 1976-05-24 | 1978-09-19 | Rohm And Haas Company | 1-Aryl-4-pyridones |
| CA1110234A (en) * | 1978-01-18 | 1981-10-06 | Hoffmann-La Roche Limited | 4-pyridone-3-carboxylic acids and process for the preparation thereof |
-
1981
- 1981-05-07 AU AU70241/81A patent/AU539399B2/en not_active Ceased
- 1981-05-07 ZA ZA00813029A patent/ZA813029B/xx unknown
- 1981-05-07 NZ NZ197027A patent/NZ197027A/en unknown
- 1981-05-11 EP EP81302079A patent/EP0040082B1/en not_active Expired
- 1981-05-11 AT AT81302079T patent/ATE7195T1/de active
- 1981-05-11 EG EG255/81A patent/EG15674A/xx active
- 1981-05-11 DE DE8181302079T patent/DE3163277D1/de not_active Expired
- 1981-05-12 JP JP56071266A patent/JPS57114573A/ja active Granted
- 1981-05-12 IL IL62855A patent/IL62855A/xx not_active IP Right Cessation
-
1982
- 1982-05-17 ES ES512283A patent/ES8304404A1/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| JPS57114573A (en) | 1982-07-16 |
| IL62855A (en) | 1984-05-31 |
| ATE7195T1 (de) | 1984-05-15 |
| ES512283A0 (es) | 1983-03-01 |
| ZA813029B (en) | 1982-05-26 |
| AU539399B2 (en) | 1984-09-27 |
| EG15674A (en) | 1986-09-30 |
| JPS6366314B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1988-12-20 |
| AU7024181A (en) | 1981-11-19 |
| ES8304404A1 (es) | 1983-03-01 |
| EP0040082B1 (en) | 1984-04-25 |
| DE3163277D1 (en) | 1984-05-30 |
| EP0040082A1 (en) | 1981-11-18 |
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