GB1596611A - 1,4-dihydro-4-oxo-6-alkyl-pyridazine-3-carboxylic acid derivatives thereof and their use as plant growth regulants - Google Patents
1,4-dihydro-4-oxo-6-alkyl-pyridazine-3-carboxylic acid derivatives thereof and their use as plant growth regulants Download PDFInfo
- Publication number
- GB1596611A GB1596611A GB7638/78A GB763878A GB1596611A GB 1596611 A GB1596611 A GB 1596611A GB 7638/78 A GB7638/78 A GB 7638/78A GB 763878 A GB763878 A GB 763878A GB 1596611 A GB1596611 A GB 1596611A
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- GB
- United Kingdom
- Prior art keywords
- alkyl
- compounds
- compound
- cereal grain
- parent
- 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
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- 230000008635 plant growth Effects 0.000 title abstract description 6
- 150000001875 compounds Chemical class 0.000 claims abstract description 64
- 206010021929 Infertility male Diseases 0.000 claims abstract description 19
- 208000007466 Male Infertility Diseases 0.000 claims abstract description 19
- 150000003839 salts Chemical class 0.000 claims abstract description 15
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 12
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 7
- 238000004519 manufacturing process Methods 0.000 claims abstract description 4
- 238000000034 method Methods 0.000 claims description 42
- 241000196324 Embryophyta Species 0.000 claims description 29
- 125000004432 carbon atom Chemical group C* 0.000 claims description 23
- 238000009396 hybridization Methods 0.000 claims description 20
- 239000000203 mixture Substances 0.000 claims description 19
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 18
- 239000004464 cereal grain Substances 0.000 claims description 16
- -1 trifluoromethylphenyl Chemical group 0.000 claims description 15
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 14
- 125000001246 bromo group Chemical group Br* 0.000 claims description 12
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 125000001424 substituent group Chemical group 0.000 claims description 9
- 125000003545 alkoxy group Chemical group 0.000 claims description 8
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 8
- 240000008042 Zea mays Species 0.000 claims description 7
- 235000002017 Zea mays subsp mays Nutrition 0.000 claims description 7
- 229910052794 bromium Chemical group 0.000 claims description 7
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 7
- 229910052736 halogen Inorganic materials 0.000 claims description 7
- 150000002367 halogens Chemical class 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 7
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 7
- 241000209140 Triticum Species 0.000 claims description 6
- 235000021307 Triticum Nutrition 0.000 claims description 6
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 6
- 239000000460 chlorine Substances 0.000 claims description 6
- 230000001939 inductive effect Effects 0.000 claims description 6
- 230000021121 meiosis Effects 0.000 claims description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 5
- 240000005979 Hordeum vulgare Species 0.000 claims description 5
- 235000007340 Hordeum vulgare Nutrition 0.000 claims description 5
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 5
- 230000015572 biosynthetic process Effects 0.000 claims description 5
- 125000005059 halophenyl group Chemical group 0.000 claims description 5
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 5
- 125000001624 naphthyl group Chemical group 0.000 claims description 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 5
- 239000007921 spray Substances 0.000 claims description 5
- 240000007594 Oryza sativa Species 0.000 claims description 4
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- 125000005083 alkoxyalkoxy group Chemical group 0.000 claims description 4
- 125000003282 alkyl amino group Chemical group 0.000 claims description 4
- 125000005115 alkyl carbamoyl group Chemical group 0.000 claims description 4
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 4
- 125000004414 alkyl thio group Chemical group 0.000 claims description 4
- 125000004181 carboxyalkyl group Chemical group 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 4
- 125000005117 dialkylcarbamoyl group Chemical group 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 235000009566 rice Nutrition 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 claims description 3
- 125000004423 acyloxy group Chemical group 0.000 claims description 3
- 125000005236 alkanoylamino group Chemical group 0.000 claims description 3
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 3
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 3
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 3
- 125000001188 haloalkyl group Chemical group 0.000 claims description 3
- 238000003306 harvesting Methods 0.000 claims description 3
- 239000007788 liquid Substances 0.000 claims description 3
- 235000009973 maize Nutrition 0.000 claims description 3
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 3
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 3
- 229940124530 sulfonamide Drugs 0.000 claims description 3
- 150000003456 sulfonamides Chemical class 0.000 claims description 3
- 238000012360 testing method Methods 0.000 claims description 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 2
- 239000000428 dust Substances 0.000 claims description 2
- 229910052740 iodine Inorganic materials 0.000 claims description 2
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 claims 1
- 238000007429 general method Methods 0.000 claims 1
- 150000002431 hydrogen Chemical group 0.000 claims 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 abstract description 11
- 230000001105 regulatory effect Effects 0.000 abstract description 5
- 235000013339 cereals Nutrition 0.000 abstract description 4
- 230000006698 induction Effects 0.000 abstract description 2
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical class [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 abstract 1
- ORTFAQDWJHRMNX-UHFFFAOYSA-N hydroxidooxidocarbon(.) Chemical compound O[C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-N 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 17
- 238000002360 preparation method Methods 0.000 description 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- 239000002904 solvent Substances 0.000 description 8
- 239000000126 substance Substances 0.000 description 7
- ZPSJGADGUYYRKE-UHFFFAOYSA-N 2H-pyran-2-one Chemical compound O=C1C=CC=CO1 ZPSJGADGUYYRKE-UHFFFAOYSA-N 0.000 description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 238000013459 approach Methods 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- 230000012010 growth Effects 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 235000005822 corn Nutrition 0.000 description 4
- 239000004495 emulsifiable concentrate Substances 0.000 description 4
- 239000003995 emulsifying agent Substances 0.000 description 4
- 208000000509 infertility Diseases 0.000 description 4
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- 208000021267 infertility disease Diseases 0.000 description 4
- 230000005764 inhibitory process Effects 0.000 description 4
- 239000004094 surface-active agent Substances 0.000 description 4
- NSYSSMYQPLSPOD-UHFFFAOYSA-N triacetate lactone Chemical compound CC1=CC(O)=CC(=O)O1 NSYSSMYQPLSPOD-UHFFFAOYSA-N 0.000 description 4
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 description 3
- JDEKUYKSOCTBJT-UHFFFAOYSA-N 1-(4-chlorophenyl)-6-methyl-4-oxopyridazine-3-carboxylic acid Chemical compound CC1=CC(=O)C(C(O)=O)=NN1C1=CC=C(Cl)C=C1 JDEKUYKSOCTBJT-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 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
- 239000002671 adjuvant Substances 0.000 description 3
- 150000001768 cations Chemical class 0.000 description 3
- 239000002270 dispersing agent Substances 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
- 230000035558 fertility Effects 0.000 description 3
- 230000009969 flowable effect Effects 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 150000007857 hydrazones Chemical class 0.000 description 3
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 235000010288 sodium nitrite Nutrition 0.000 description 3
- 239000002689 soil Substances 0.000 description 3
- 239000000080 wetting agent Substances 0.000 description 3
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 2
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 2
- VWFQMTCKWLWHJV-UHFFFAOYSA-N 1-(4-fluorophenyl)-6-methyl-4-oxopyridazine-3-carboxylic acid Chemical compound CC1=CC(=O)C(C(O)=O)=NN1C1=CC=C(F)C=C1 VWFQMTCKWLWHJV-UHFFFAOYSA-N 0.000 description 2
- IYLQQYCKWAAZLD-UHFFFAOYSA-N 6-methyl-4-oxo-1-phenylpyridazine-3-carboxylic acid Chemical compound CC1=CC(=O)C(C(O)=O)=NN1C1=CC=CC=C1 IYLQQYCKWAAZLD-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
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical class C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
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- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
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- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
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- 235000013305 food Nutrition 0.000 description 2
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- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 2
- 239000012669 liquid formulation Substances 0.000 description 2
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- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
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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 1
- UDPGUMQDCGORJQ-UHFFFAOYSA-N (2-chloroethyl)phosphonic acid Chemical compound OP(O)(=O)CCCl UDPGUMQDCGORJQ-UHFFFAOYSA-N 0.000 description 1
- CJAAPVQEZPAQNI-UHFFFAOYSA-N (2-methylphenyl)methanamine Chemical compound CC1=CC=CC=C1CN CJAAPVQEZPAQNI-UHFFFAOYSA-N 0.000 description 1
- GHYOCDFICYLMRF-UTIIJYGPSA-N (2S,3R)-N-[(2S)-3-(cyclopenten-1-yl)-1-[(2R)-2-methyloxiran-2-yl]-1-oxopropan-2-yl]-3-hydroxy-3-(4-methoxyphenyl)-2-[[(2S)-2-[(2-morpholin-4-ylacetyl)amino]propanoyl]amino]propanamide Chemical compound C1(=CCCC1)C[C@@H](C(=O)[C@@]1(OC1)C)NC([C@H]([C@@H](C1=CC=C(C=C1)OC)O)NC([C@H](C)NC(CN1CCOCC1)=O)=O)=O GHYOCDFICYLMRF-UTIIJYGPSA-N 0.000 description 1
- 125000003837 (C1-C20) alkyl 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
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- CVPJFGYRACDMPA-UHFFFAOYSA-N 1-(2-chloro-4-methylphenyl)-6-methyl-4-oxopyridazine-3-carboxylic acid Chemical compound ClC1=CC(C)=CC=C1N1C(C)=CC(=O)C(C(O)=O)=N1 CVPJFGYRACDMPA-UHFFFAOYSA-N 0.000 description 1
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- RNLQLHVDFKWDNN-UHFFFAOYSA-N 1-(3-bromophenyl)-6-methyl-4-oxopyridazine-3-carboxylic acid Chemical compound CC1=CC(=O)C(C(O)=O)=NN1C1=CC=CC(Br)=C1 RNLQLHVDFKWDNN-UHFFFAOYSA-N 0.000 description 1
- AUNXJUKTLFEODP-UHFFFAOYSA-N 1-(3-chlorophenyl)-6-methyl-4-oxopyridazine-3-carboxylic acid Chemical compound CC1=CC(=O)C(C(O)=O)=NN1C1=CC=CC(Cl)=C1 AUNXJUKTLFEODP-UHFFFAOYSA-N 0.000 description 1
- LZFSVNPIAVORRY-UHFFFAOYSA-N 1-(3-fluorophenyl)-6-methyl-4-oxopyridazine-3-carboxylic acid Chemical compound CC1=CC(=O)C(C(O)=O)=NN1C1=CC=CC(F)=C1 LZFSVNPIAVORRY-UHFFFAOYSA-N 0.000 description 1
- MHNAGWXEYZZHGX-UHFFFAOYSA-N 1-(4-bromophenyl)-6-methyl-4-oxopyridazine-3-carboxylic acid Chemical compound CC1=CC(=O)C(C(O)=O)=NN1C1=CC=C(Br)C=C1 MHNAGWXEYZZHGX-UHFFFAOYSA-N 0.000 description 1
- SPYMPOBCTWGOOK-UHFFFAOYSA-N 1-(4-chlorophenyl)-5,6-dimethyl-4-oxopyridazine-3-carboxylic acid Chemical compound CC1=C(C)C(=O)C(C(O)=O)=NN1C1=CC=C(Cl)C=C1 SPYMPOBCTWGOOK-UHFFFAOYSA-N 0.000 description 1
- BBIHAPNDJDAHIT-UHFFFAOYSA-N 1-(4-chlorophenyl)-6-ethyl-4-oxopyridazine-3-carboxylic acid Chemical compound CCC1=CC(=O)C(C(O)=O)=NN1C1=CC=C(Cl)C=C1 BBIHAPNDJDAHIT-UHFFFAOYSA-N 0.000 description 1
- PKLSIIOULSCBKF-UHFFFAOYSA-N 1-(4-iodophenyl)-6-methyl-4-oxopyridazine-3-carboxylic acid Chemical compound CC1=CC(=O)C(C(O)=O)=NN1C1=CC=C(I)C=C1 PKLSIIOULSCBKF-UHFFFAOYSA-N 0.000 description 1
- ONBQEOIKXPHGMB-VBSBHUPXSA-N 1-[2-[(2s,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-4,6-dihydroxyphenyl]-3-(4-hydroxyphenyl)propan-1-one Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1OC1=CC(O)=CC(O)=C1C(=O)CCC1=CC=C(O)C=C1 ONBQEOIKXPHGMB-VBSBHUPXSA-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
- 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
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- 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
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-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
- 230000017260 vegetative to reproductive phase transition of meristem 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
-
- 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
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/58—1,2-Diazines; Hydrogenated 1,2-diazines
-
- 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
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
- A01N47/22—O-Aryl or S-Aryl esters thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
- C07D237/02—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings
- C07D237/06—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D237/10—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three 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, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D237/24—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Environmental Sciences (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Genetics & Genomics (AREA)
- Plant Pathology (AREA)
- Developmental Biology & Embryology (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Botany (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Breeding Of Plants And Reproduction By Means Of Culturing (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US77639477A | 1977-03-10 | 1977-03-10 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1596611A true GB1596611A (en) | 1981-08-26 |
Family
ID=25107257
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB7638/78A Expired GB1596611A (en) | 1977-03-10 | 1978-02-27 | 1,4-dihydro-4-oxo-6-alkyl-pyridazine-3-carboxylic acid derivatives thereof and their use as plant growth regulants |
Country Status (27)
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0089137A1 (en) * | 1982-03-04 | 1983-09-21 | Rohm And Haas Company | Substituted pyridazines, their use as plant growth regulators, and plant growth regulating compositions containing them |
| US5169429A (en) * | 1988-10-14 | 1992-12-08 | Monsanto Company | Hybridization of sunflowers and safflowers |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1138872A (en) * | 1979-07-30 | 1983-01-04 | Rohm And Haas Company | Process for the preparation of 1-aryl-1,4- dihydro-4-oxopyridazine-3-carboxamides |
| CA1132566A (en) * | 1979-07-30 | 1982-09-28 | Glenn R. Carlson | Process for the preparation of 1-aryl-1, 4-dihydro-4-oxopyridazine-3-carboxylic acid esters |
| EP0037133A1 (en) * | 1980-03-26 | 1981-10-07 | Shell Internationale Researchmaatschappij B.V. | Pyridazinone compounds, process for their preparation, compositions containing them and a method of regulating the growth of plants, increasing the yield of soya bean plants and sterilizing the male anthers of plants, including small grain cereal plants, using them as well as a method of producing F1 hybrid seed |
| GR75799B (enrdf_load_stackoverflow) * | 1980-10-03 | 1984-08-02 | Ici Plc | |
| US5062880A (en) * | 1980-10-03 | 1991-11-05 | Monsanto Company | 1-aryl-1,4-dihydro-4-oxo-5-carboxypyridazine derivatives and their use as plant growth regulators and hybridizing agents |
| AR230050A1 (es) * | 1980-10-03 | 1984-02-29 | Rohm & Haas | Compuesto derivado de 1-fenil-1,4-dihidro-4-oxo-3,5-dicarboxipirazina,composicion que lo comprende y procedimientos para repararlo |
| US4707181A (en) * | 1980-10-03 | 1987-11-17 | Rohm And Haas Company | 1-aryl-1,4-dihydro-4-oxo-3,5-dicarboxypyridazine derivatives and their use as plant growth regulators and hybridizing agents |
| US4732603A (en) * | 1980-10-03 | 1988-03-22 | Rohm And Haas Company | 1-aryl-1,4-dihydro-4-oxo-5-carboxypyridazine derivatives and their use as plant growth regulators and hybridizing agents |
| CA1166646A (en) * | 1981-02-20 | 1984-05-01 | Thomas R. Opie | Process for the preparation of 4-hydroxy-6-methyl-2- pyrone |
| US4623378A (en) * | 1983-08-10 | 1986-11-18 | Ciba-Geigy Corporation | Gametocidal pyridazinylcarboxylic acid derivatives |
| FR2648135B1 (fr) * | 1989-06-07 | 1991-09-27 | Pf Medicament | Derives de phenyl-1-dihydro-1,4 amino-3 oxo-4 pyridazines, leur preparation et leur application en therapeutique |
| WO1991000688A1 (en) * | 1989-07-07 | 1991-01-24 | Vsesojuzny Nauchno-Issledovatelsky Institut Selskokhozyaistvennoi Biotekhnologii | Method for sterilization of plant anthers |
| FR2676733B1 (fr) * | 1991-05-22 | 1993-10-01 | Fabre Medicament Pierre | Derives de phenyl-1 dihydro-1,4 hydroxy-3 oxo-4 pyridazines, leur preparation et leur application en therapeutique. |
| CA2372002A1 (en) | 1999-02-02 | 2000-08-10 | Monsanto Technology Llc | Production of phosphonopyrazoles |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2454742A (en) * | 1948-11-23 | Pyridazone derivatives and method | ||
| US2835671A (en) * | 1958-05-20 | Pyridazine derivatives | ||
| DE954332C (de) * | 1953-05-12 | 1956-12-13 | Ciba Geigy | Verfahren zur Herstellung neuer Ester |
-
1977
- 1977-03-10 PL PL1977205233A patent/PL115813B1/pl unknown
-
1978
- 1978-02-03 SE SE7801307A patent/SE446812B/sv not_active IP Right Cessation
- 1978-02-23 IL IL54122A patent/IL54122A/xx unknown
- 1978-02-27 AR AR271235A patent/AR219522A1/es active
- 1978-02-27 GB GB7638/78A patent/GB1596611A/en not_active Expired
- 1978-02-27 CA CA297,781A patent/CA1103477A/en not_active Expired
- 1978-02-28 TR TR20326A patent/TR20326A/xx unknown
- 1978-03-01 DE DE19782808795 patent/DE2808795A1/de active Granted
- 1978-03-01 DE DE2858755A patent/DE2858755C2/de not_active Expired - Lifetime
- 1978-03-01 NZ NZ186596A patent/NZ186596A/xx unknown
- 1978-03-03 ES ES467543A patent/ES467543A1/es not_active Expired
- 1978-03-04 GR GR55611A patent/GR64069B/el unknown
- 1978-03-06 CS CS781414A patent/CS199719B2/cs unknown
- 1978-03-07 EG EG150/78A patent/EG13401A/xx active
- 1978-03-07 PT PT67747A patent/PT67747A/pt unknown
- 1978-03-07 DD DD78204010A patent/DD140410A5/de unknown
- 1978-03-07 FR FR7806494A patent/FR2383605A1/fr active Granted
- 1978-03-07 BR BR7801362A patent/BR7801362A/pt unknown
- 1978-03-08 CH CH251278A patent/CH629077A5/fr not_active IP Right Cessation
- 1978-03-08 AU AU33980/78A patent/AU524926B2/en not_active Expired
- 1978-03-09 BE BE185777A patent/BE864704A/xx not_active IP Right Cessation
- 1978-03-09 IT IT67511/78A patent/IT1111613B/it active
- 1978-03-09 DK DK106078A patent/DK156607C/da not_active IP Right Cessation
- 1978-03-09 HU HU78RO969A patent/HU182990B/hu unknown
- 1978-03-09 BG BG038956A patent/BG34901A3/xx unknown
- 1978-03-09 JP JP2714478A patent/JPS53133633A/ja active Granted
- 1978-03-10 ZA ZA00781424A patent/ZA781424B/xx unknown
- 1978-03-10 PL PL20523378A patent/PL205233A1/xx unknown
- 1978-03-10 NL NLAANVRAGE7802656,A patent/NL171118C/xx not_active IP Right Cessation
- 1978-07-24 FR FR7821842A patent/FR2392980A1/fr active Granted
-
1985
- 1985-07-05 SE SE8503365A patent/SE469585B/sv not_active IP Right Cessation
-
1987
- 1987-03-09 JP JP62053913A patent/JPS62265204A/ja active Granted
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0089137A1 (en) * | 1982-03-04 | 1983-09-21 | Rohm And Haas Company | Substituted pyridazines, their use as plant growth regulators, and plant growth regulating compositions containing them |
| US5169429A (en) * | 1988-10-14 | 1992-12-08 | Monsanto Company | Hybridization of sunflowers and safflowers |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| 732 | Registration of transactions, instruments or events in the register (sect. 32/1977) | ||
| PE20 | Patent expired after termination of 20 years |
Effective date: 19980226 |