JPH0567625B2 - - Google Patents
Info
- Publication number
- JPH0567625B2 JPH0567625B2 JP56156321A JP15632181A JPH0567625B2 JP H0567625 B2 JPH0567625 B2 JP H0567625B2 JP 56156321 A JP56156321 A JP 56156321A JP 15632181 A JP15632181 A JP 15632181A JP H0567625 B2 JPH0567625 B2 JP H0567625B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- formula
- substituted
- unsubstituted phenyl
- phenyl group
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 150000001875 compounds Chemical class 0.000 claims description 58
- 239000000203 mixture Substances 0.000 claims description 25
- -1 alkali metal salt Chemical class 0.000 claims description 23
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 23
- 238000000034 method Methods 0.000 claims description 18
- 150000003839 salts Chemical class 0.000 claims description 15
- 239000002253 acid Substances 0.000 claims description 14
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- 238000006243 chemical reaction Methods 0.000 claims description 11
- 206010021929 Infertility male Diseases 0.000 claims description 10
- 208000007466 Male Infertility Diseases 0.000 claims description 10
- 229910052783 alkali metal Inorganic materials 0.000 claims description 10
- 239000012954 diazonium Substances 0.000 claims description 10
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 9
- 125000001624 naphthyl group Chemical group 0.000 claims description 9
- 125000001424 substituent group Chemical group 0.000 claims description 9
- 150000001989 diazonium salts Chemical class 0.000 claims description 8
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 7
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 7
- 235000013339 cereals Nutrition 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 150000002367 halogens Chemical class 0.000 claims description 6
- IUYHWZFSGMZEOG-UHFFFAOYSA-M magnesium;propane;chloride Chemical compound [Mg+2].[Cl-].C[CH-]C IUYHWZFSGMZEOG-UHFFFAOYSA-M 0.000 claims description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 5
- ZPSJGADGUYYRKE-UHFFFAOYSA-N 2H-pyran-2-one Chemical compound O=C1C=CC=CO1 ZPSJGADGUYYRKE-UHFFFAOYSA-N 0.000 claims description 5
- 150000007857 hydrazones Chemical class 0.000 claims description 5
- RNJOKCPFLQMDEC-UHFFFAOYSA-N 4(R),8-dimethyl-trans-2-nonenoyl-CoA Chemical compound COC(=O)CC(=O)CC(=O)OC RNJOKCPFLQMDEC-UHFFFAOYSA-N 0.000 claims description 4
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 4
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 claims description 4
- 239000012346 acetyl chloride Substances 0.000 claims description 4
- 230000002378 acidificating effect Effects 0.000 claims description 4
- 239000012312 sodium hydride Substances 0.000 claims description 4
- 229910000104 sodium hydride Inorganic materials 0.000 claims description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 3
- 239000012298 atmosphere Substances 0.000 claims description 3
- 230000001939 inductive effect Effects 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 2
- VNZOLPIHDIJPBZ-UHFFFAOYSA-N 4-hydroxypyran-2-one Chemical compound OC=1C=COC(=O)C=1 VNZOLPIHDIJPBZ-UHFFFAOYSA-N 0.000 claims description 2
- 239000002585 base Substances 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 230000021121 meiosis Effects 0.000 claims description 2
- 239000012442 inert solvent Substances 0.000 claims 3
- 235000013411 Alpinia speciosa Nutrition 0.000 claims 2
- 244000060696 Alpinia speciosa Species 0.000 claims 2
- 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 claims 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- 241000196324 Embryophyta Species 0.000 description 22
- 239000000243 solution Substances 0.000 description 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 239000003795 chemical substances by application Substances 0.000 description 13
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- 239000000126 substance Substances 0.000 description 12
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 10
- 239000000843 powder Substances 0.000 description 10
- 230000015572 biosynthetic process Effects 0.000 description 8
- 238000003786 synthesis reaction Methods 0.000 description 8
- 239000000839 emulsion Substances 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 230000000694 effects Effects 0.000 description 5
- 230000012010 growth Effects 0.000 description 5
- 239000002002 slurry Substances 0.000 description 5
- 230000017260 vegetative to reproductive phase transition of meristem Effects 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 4
- 239000002671 adjuvant Substances 0.000 description 4
- 150000005690 diesters Chemical class 0.000 description 4
- 238000000921 elemental analysis Methods 0.000 description 4
- 239000003995 emulsifying agent Substances 0.000 description 4
- 239000008187 granular material Substances 0.000 description 4
- 238000009396 hybridization Methods 0.000 description 4
- 230000005764 inhibitory process Effects 0.000 description 4
- 239000005648 plant growth regulator Substances 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- JUSIWJONLKBPDU-UHFFFAOYSA-N pyridazine-4-carboxylic acid Chemical class OC(=O)C1=CC=NN=C1 JUSIWJONLKBPDU-UHFFFAOYSA-N 0.000 description 4
- 239000001632 sodium acetate Substances 0.000 description 4
- 235000017281 sodium acetate Nutrition 0.000 description 4
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
- 239000002689 soil Substances 0.000 description 4
- 239000004094 surface-active agent Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000004480 active ingredient Substances 0.000 description 3
- 239000000538 analytical sample Substances 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 239000002270 dispersing agent Substances 0.000 description 3
- 230000035558 fertility Effects 0.000 description 3
- 230000009969 flowable effect Effects 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 235000019198 oils Nutrition 0.000 description 3
- 150000004892 pyridazines Chemical class 0.000 description 3
- 230000001105 regulatory effect Effects 0.000 description 3
- 230000004044 response Effects 0.000 description 3
- 241000894007 species Species 0.000 description 3
- 239000007921 spray Substances 0.000 description 3
- 238000011282 treatment Methods 0.000 description 3
- 239000000080 wetting agent Substances 0.000 description 3
- OXTNCQMOKLOUAM-UHFFFAOYSA-N 3-Oxoglutaric acid Chemical compound OC(=O)CC(=O)CC(O)=O OXTNCQMOKLOUAM-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
- HDSKJRZKLHXPNF-UHFFFAOYSA-M 4-chlorobenzenediazonium;chloride Chemical compound [Cl-].ClC1=CC=C([N+]#N)C=C1 HDSKJRZKLHXPNF-UHFFFAOYSA-M 0.000 description 2
- PSMIHCDKMNXTAY-UHFFFAOYSA-N 6-oxo-1h-pyridazine-4-carboxylic acid Chemical class OC(=O)C=1C=NNC(=O)C=1 PSMIHCDKMNXTAY-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 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
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 240000008042 Zea mays Species 0.000 description 2
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 238000013459 approach Methods 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 230000033228 biological regulation Effects 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 238000006114 decarboxylation reaction Methods 0.000 description 2
- 229910001873 dinitrogen Inorganic materials 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 239000000417 fungicide Substances 0.000 description 2
- 239000010903 husk Substances 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 208000000509 infertility Diseases 0.000 description 2
- 230000036512 infertility Effects 0.000 description 2
- 208000021267 infertility disease Diseases 0.000 description 2
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical group [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 235000015170 shellfish Nutrition 0.000 description 2
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 2
- 235000012239 silicon dioxide Nutrition 0.000 description 2
- 235000010288 sodium nitrite Nutrition 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- 125000004953 trihalomethyl group Chemical group 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- UDPGUMQDCGORJQ-UHFFFAOYSA-N (2-chloroethyl)phosphonic acid Chemical compound OP(O)(=O)CCCl UDPGUMQDCGORJQ-UHFFFAOYSA-N 0.000 description 1
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- QJVLBDXSSXUYPP-UHFFFAOYSA-N 1-(4-chlorophenyl)-5-methoxycarbonyl-6-methyl-4-oxopyridazine-3-carboxylic acid Chemical compound N1=C(C(O)=O)C(=O)C(C(=O)OC)=C(C)N1C1=CC=C(Cl)C=C1 QJVLBDXSSXUYPP-UHFFFAOYSA-N 0.000 description 1
- KBMWJHGYCPQNAN-UHFFFAOYSA-N 2-(2-bromophenyl)-3-butyl-5-oxopyridazine-4-carboxylic acid Chemical compound CCCCC1=C(C(O)=O)C(=O)C=NN1C1=CC=CC=C1Br KBMWJHGYCPQNAN-UHFFFAOYSA-N 0.000 description 1
- JOORBISBNNSCES-UHFFFAOYSA-N 2-(2-chlorophenyl)-3-ethyl-5-oxopyridazine-4-carboxylic acid Chemical compound CCC1=C(C(O)=O)C(=O)C=NN1C1=CC=CC=C1Cl JOORBISBNNSCES-UHFFFAOYSA-N 0.000 description 1
- WRJKSMQEMVCGSW-UHFFFAOYSA-N 2-(3,4-dichlorophenyl)-5-oxo-3-propylpyridazine-4-carboxylic acid Chemical compound CCCC1=C(C(O)=O)C(=O)C=NN1C1=CC=C(Cl)C(Cl)=C1 WRJKSMQEMVCGSW-UHFFFAOYSA-N 0.000 description 1
- KLIQZXNQAVBWMC-UHFFFAOYSA-N 2-(3-bromophenyl)-5-oxo-3-propylpyridazine-4-carboxylic acid Chemical compound CCCC1=C(C(O)=O)C(=O)C=NN1C1=CC=CC(Br)=C1 KLIQZXNQAVBWMC-UHFFFAOYSA-N 0.000 description 1
- TXMLZWYUHDVTAG-UHFFFAOYSA-N 2-(3-chlorophenyl)-3-methyl-5-oxopyridazine-4-carboxylic acid Chemical compound CC1=C(C(O)=O)C(=O)C=NN1C1=CC=CC(Cl)=C1 TXMLZWYUHDVTAG-UHFFFAOYSA-N 0.000 description 1
- WKNOBLOJDFGOOB-UHFFFAOYSA-N 2-(3-ethoxyphenyl)-3-ethyl-5-oxopyridazine-4-carboxylic acid Chemical compound CCOC1=CC=CC(N2C(=C(C(O)=O)C(=O)C=N2)CC)=C1 WKNOBLOJDFGOOB-UHFFFAOYSA-N 0.000 description 1
- IBNZXDCUJDVUDC-UHFFFAOYSA-N 2-(4-bromophenyl)-3-ethyl-5-oxopyridazine-4-carboxylic acid Chemical compound CCC1=C(C(O)=O)C(=O)C=NN1C1=CC=C(Br)C=C1 IBNZXDCUJDVUDC-UHFFFAOYSA-N 0.000 description 1
- FASWREUVTUDWOG-UHFFFAOYSA-N 2-(4-chlorophenyl)-3-methyl-5-oxopyridazine-4-carboxylic acid Chemical compound CC1=C(C(O)=O)C(=O)C=NN1C1=CC=C(Cl)C=C1 FASWREUVTUDWOG-UHFFFAOYSA-N 0.000 description 1
- HKTJZMNHDKYIJN-UHFFFAOYSA-N 2-(4-chlorophenyl)-5-oxo-3-phenylpyridazine-4-carboxylic acid Chemical compound C=1C=C(Cl)C=CC=1N1N=CC(=O)C(C(=O)O)=C1C1=CC=CC=C1 HKTJZMNHDKYIJN-UHFFFAOYSA-N 0.000 description 1
- MEHULTSZBCQLDS-UHFFFAOYSA-N 2-(4-methylphenyl)-5-oxo-3-phenylpyridazine-4-carboxylic acid Chemical compound C1=CC(C)=CC=C1N1C(C=2C=CC=CC=2)=C(C(O)=O)C(=O)C=N1 MEHULTSZBCQLDS-UHFFFAOYSA-N 0.000 description 1
- BDULWRHKOVILGA-UHFFFAOYSA-N 2-[2-chloro-5-(trifluoromethyl)phenyl]-3-ethyl-5-oxopyridazine-4-carboxylic acid Chemical compound CCC1=C(C(O)=O)C(=O)C=NN1C1=CC(C(F)(F)F)=CC=C1Cl BDULWRHKOVILGA-UHFFFAOYSA-N 0.000 description 1
- WIYSSUCEZYTYBK-UHFFFAOYSA-N 2-[4-bromo-2-(trifluoromethyl)phenyl]-3-ethyl-5-oxopyridazine-4-carboxylic acid Chemical compound CCC1=C(C(O)=O)C(=O)C=NN1C1=CC=C(Br)C=C1C(F)(F)F WIYSSUCEZYTYBK-UHFFFAOYSA-N 0.000 description 1
- YOQFAIANWURLBR-UHFFFAOYSA-N 2-[4-chloro-2-(trifluoromethyl)phenyl]-3-methyl-5-oxopyridazine-4-carboxylic acid Chemical compound CC1=C(C(O)=O)C(=O)C=NN1C1=CC=C(Cl)C=C1C(F)(F)F YOQFAIANWURLBR-UHFFFAOYSA-N 0.000 description 1
- MPNXSZJPSVBLHP-UHFFFAOYSA-N 2-chloro-n-phenylpyridine-3-carboxamide Chemical compound ClC1=NC=CC=C1C(=O)NC1=CC=CC=C1 MPNXSZJPSVBLHP-UHFFFAOYSA-N 0.000 description 1
- RMIOYNNSZIIFSK-UHFFFAOYSA-N 3-benzyl-2-(2-chloro-4-methylphenyl)-5-oxopyridazine-4-carboxylic acid Chemical compound ClC1=CC(C)=CC=C1N1C(CC=2C=CC=CC=2)=C(C(O)=O)C(=O)C=N1 RMIOYNNSZIIFSK-UHFFFAOYSA-N 0.000 description 1
- ACBGVAPMCSHONF-UHFFFAOYSA-N 3-benzyl-5-oxo-2-(2,4,6-trichlorophenyl)pyridazine-4-carboxylic acid Chemical compound ClC=1C=C(Cl)C=C(Cl)C=1N1N=CC(=O)C(C(=O)O)=C1CC1=CC=CC=C1 ACBGVAPMCSHONF-UHFFFAOYSA-N 0.000 description 1
- ZWPFPNXTPCJVRV-UHFFFAOYSA-N 3-butyl-2-(3-cyanophenyl)-5-oxopyridazine-4-carboxylic acid Chemical compound CCCCC1=C(C(O)=O)C(=O)C=NN1C1=CC=CC(C#N)=C1 ZWPFPNXTPCJVRV-UHFFFAOYSA-N 0.000 description 1
- CATFTTNIMHVMAF-UHFFFAOYSA-N 3-butyl-2-(4-iodophenyl)-5-oxopyridazine-4-carboxylic acid Chemical compound CCCCC1=C(C(O)=O)C(=O)C=NN1C1=CC=C(I)C=C1 CATFTTNIMHVMAF-UHFFFAOYSA-N 0.000 description 1
- LMQWJTKEPOAVEA-UHFFFAOYSA-N 3-butyl-2-naphthalen-2-yl-5-oxopyridazine-4-carboxylic acid Chemical compound CCCCC1=C(C(O)=O)C(=O)C=NN1C1=CC=C(C=CC=C2)C2=C1 LMQWJTKEPOAVEA-UHFFFAOYSA-N 0.000 description 1
- XFMWNOYAJBPSJK-UHFFFAOYSA-N 3-butyl-5-oxo-2-phenylpyridazine-4-carboxylic acid Chemical compound CCCCC1=C(C(O)=O)C(=O)C=NN1C1=CC=CC=C1 XFMWNOYAJBPSJK-UHFFFAOYSA-N 0.000 description 1
- VUEZBQJWLDBIDE-UHFFFAOYSA-N 3-ethenyl-1,3-oxazolidin-2-one Chemical compound C=CN1CCOC1=O VUEZBQJWLDBIDE-UHFFFAOYSA-N 0.000 description 1
- KYNXPNLIWPKSQR-UHFFFAOYSA-N 3-ethyl-5-oxo-2-phenylpyridazine-4-carboxylic acid Chemical compound CCC1=C(C(O)=O)C(=O)C=NN1C1=CC=CC=C1 KYNXPNLIWPKSQR-UHFFFAOYSA-N 0.000 description 1
- JQEGHLJYFPTTMC-UHFFFAOYSA-N 3-methyl-5-oxo-2-[4-(trifluoromethyl)phenyl]pyridazine-4-carboxylic acid Chemical compound CC1=C(C(O)=O)C(=O)C=NN1C1=CC=C(C(F)(F)F)C=C1 JQEGHLJYFPTTMC-UHFFFAOYSA-N 0.000 description 1
- AQSQYYQVUUTUPW-UHFFFAOYSA-N 3-methyl-5-oxo-2-phenylpyridazine-4-carboxylic acid Chemical compound CC1=C(C(O)=O)C(=O)C=NN1C1=CC=CC=C1 AQSQYYQVUUTUPW-UHFFFAOYSA-N 0.000 description 1
- JUTZOCMJCOGLNK-UHFFFAOYSA-N 4-hydrazinyl-3,3-dimethyl-4-oxobutanoic acid Chemical compound OC(=O)CC(C)(C)C(=O)NN JUTZOCMJCOGLNK-UHFFFAOYSA-N 0.000 description 1
- RZZFZDIRHDDPNF-UHFFFAOYSA-N 5-oxo-2,3-diphenylpyridazine-4-carboxylic acid Chemical compound C=1C=CC=CC=1N1N=CC(=O)C(C(=O)O)=C1C1=CC=CC=C1 RZZFZDIRHDDPNF-UHFFFAOYSA-N 0.000 description 1
- SDGCRRSRAWOWJG-UHFFFAOYSA-N 5-oxo-2-phenyl-3-propylpyridazine-4-carboxylic acid Chemical compound CCCC1=C(C(O)=O)C(=O)C=NN1C1=CC=CC=C1 SDGCRRSRAWOWJG-UHFFFAOYSA-N 0.000 description 1
- AZNSKHLQNCKBHC-UHFFFAOYSA-N 6-oxo-1h-pyridazine-5-carboxylic acid Chemical class OC(=O)C1=CC=NN=C1O AZNSKHLQNCKBHC-UHFFFAOYSA-N 0.000 description 1
- 241001124076 Aphididae Species 0.000 description 1
- 229930192334 Auxin Natural products 0.000 description 1
- 235000007319 Avena orientalis Nutrition 0.000 description 1
- 241000209763 Avena sativa Species 0.000 description 1
- 235000007558 Avena sp Nutrition 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
- 235000008733 Citrus aurantifolia Nutrition 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- 241000221785 Erysiphales Species 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005976 Ethephon Substances 0.000 description 1
- 239000005977 Ethylene Substances 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
- 229920000663 Hydroxyethyl cellulose Polymers 0.000 description 1
- 239000004354 Hydroxyethyl cellulose Substances 0.000 description 1
- 206010021928 Infertility female Diseases 0.000 description 1
- 239000005983 Maleic hydrazide Substances 0.000 description 1
- BGRDGMRNKXEXQD-UHFFFAOYSA-N Maleic hydrazide Chemical compound OC1=CC=C(O)N=N1 BGRDGMRNKXEXQD-UHFFFAOYSA-N 0.000 description 1
- 240000007594 Oryza sativa Species 0.000 description 1
- 235000007164 Oryza sativa Nutrition 0.000 description 1
- 241000209504 Poaceae Species 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 229920002125 Sokalan® Polymers 0.000 description 1
- 240000006394 Sorghum bicolor Species 0.000 description 1
- 235000011684 Sorghum saccharatum Nutrition 0.000 description 1
- 244000062793 Sorghum vulgare Species 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 235000011941 Tilia x europaea Nutrition 0.000 description 1
- 240000006909 Tilia x europaea Species 0.000 description 1
- 235000019714 Triticale Nutrition 0.000 description 1
- 235000021307 Triticum Nutrition 0.000 description 1
- 244000098338 Triticum aestivum Species 0.000 description 1
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
- 235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 239000002363 auxin Substances 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 239000003139 biocide Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
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- 230000001488 breeding effect Effects 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
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- 229920002678 cellulose Polymers 0.000 description 1
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- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 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
- 239000004927 clay Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 239000002285 corn oil Substances 0.000 description 1
- 235000005687 corn oil Nutrition 0.000 description 1
- 238000009402 cross-breeding Methods 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
- 230000002939 deleterious effect Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical compound [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- UJWHGMCTYOZUOR-UHFFFAOYSA-N dimethyl 1-(4-chlorophenyl)-4-oxopyridazine-3,5-dicarboxylate Chemical compound N1=C(C(=O)OC)C(=O)C(C(=O)OC)=CN1C1=CC=C(Cl)C=C1 UJWHGMCTYOZUOR-UHFFFAOYSA-N 0.000 description 1
- PKVACPJZLWHKBQ-UHFFFAOYSA-N dimethyl 2,3-dioxopentanedioate Chemical compound COC(=O)CC(=O)C(=O)C(=O)OC PKVACPJZLWHKBQ-UHFFFAOYSA-N 0.000 description 1
- NFUBPGULXQIPFA-UHFFFAOYSA-N dimethyl 2-acetyl-3-oxopentanedioate Chemical compound COC(=O)CC(=O)C(C(C)=O)C(=O)OC NFUBPGULXQIPFA-UHFFFAOYSA-N 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 210000005069 ears Anatomy 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- QYDYPVFESGNLHU-UHFFFAOYSA-N elaidic acid methyl ester Natural products CCCCCCCCC=CCCCCCCCC(=O)OC QYDYPVFESGNLHU-UHFFFAOYSA-N 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 235000010944 ethyl methyl cellulose Nutrition 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000003337 fertilizer Substances 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 230000014509 gene expression Effects 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
- 235000011187 glycerol Nutrition 0.000 description 1
- 230000009036 growth inhibition Effects 0.000 description 1
- 239000001963 growth medium Substances 0.000 description 1
- 239000003630 growth substance Substances 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 230000009931 harmful effect Effects 0.000 description 1
- 230000020169 heat generation Effects 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 239000012456 homogeneous solution Substances 0.000 description 1
- 230000000887 hydrating effect Effects 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 229910052806 inorganic carbonate Inorganic materials 0.000 description 1
- 229910052909 inorganic silicate Inorganic materials 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 239000004571 lime Substances 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 235000009973 maize Nutrition 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 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 1
- OJURWUUOVGOHJZ-UHFFFAOYSA-N methyl 2-[(2-acetyloxyphenyl)methyl-[2-[(2-acetyloxyphenyl)methyl-(2-methoxy-2-oxoethyl)amino]ethyl]amino]acetate Chemical compound C=1C=CC=C(OC(C)=O)C=1CN(CC(=O)OC)CCN(CC(=O)OC)CC1=CC=CC=C1OC(C)=O OJURWUUOVGOHJZ-UHFFFAOYSA-N 0.000 description 1
- GPZLWXXKOFEKOE-UHFFFAOYSA-N methyl 4-hydroxy-2-methyl-6-oxopyran-3-carboxylate Chemical compound COC(=O)C1=C(C)OC(=O)C=C1O GPZLWXXKOFEKOE-UHFFFAOYSA-N 0.000 description 1
- QYDYPVFESGNLHU-KHPPLWFESA-N methyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC QYDYPVFESGNLHU-KHPPLWFESA-N 0.000 description 1
- 229940073769 methyl oleate Drugs 0.000 description 1
- IJFLWNYKGMQQOW-UHFFFAOYSA-N methyl pyridazine-4-carboxylate Chemical compound COC(=O)C1=CC=NN=C1 IJFLWNYKGMQQOW-UHFFFAOYSA-N 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- 229920003087 methylethyl cellulose Polymers 0.000 description 1
- 235000019713 millet Nutrition 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 150000002790 naphthalenes Chemical class 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 238000009401 outcrossing Methods 0.000 description 1
- 231100000208 phytotoxic Toxicity 0.000 description 1
- 230000000885 phytotoxic effect Effects 0.000 description 1
- 239000010665 pine oil Substances 0.000 description 1
- 230000008654 plant damage Effects 0.000 description 1
- 230000008635 plant growth Effects 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 239000004584 polyacrylic acid Substances 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000000244 polyoxyethylene sorbitan monooleate Substances 0.000 description 1
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229920000053 polysorbate 80 Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- RDQWJNPUOHXYCV-UHFFFAOYSA-N pyridazine-3,4-dicarboxylic acid Chemical class OC(=O)C1=CC=NN=C1C(O)=O RDQWJNPUOHXYCV-UHFFFAOYSA-N 0.000 description 1
- RUUOPSRRIKJHNH-UHFFFAOYSA-N pyridazine-3-carboxylic acid Chemical compound OC(=O)C1=CC=CN=N1 RUUOPSRRIKJHNH-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000009738 saturating Methods 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 238000002791 soaking Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 125000004436 sodium atom Chemical group 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 238000009331 sowing Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 230000007480 spreading Effects 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 230000007103 stamina Effects 0.000 description 1
- 210000000130 stem cell Anatomy 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
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-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
- GPRLSGONYQIRFK-MNYXATJNSA-N triton Chemical compound [3H+] GPRLSGONYQIRFK-MNYXATJNSA-N 0.000 description 1
- 238000010396 two-hybrid screening Methods 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 235000013311 vegetables Nutrition 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
- 230000003313 weakening effect Effects 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
- 241000228158 x Triticosecale Species 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
- 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
-
- 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
-
- 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
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Environmental Sciences (AREA)
- Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Dentistry (AREA)
- Engineering & Computer Science (AREA)
- Zoology (AREA)
- Plant Pathology (AREA)
- Genetics & Genomics (AREA)
- Botany (AREA)
- Developmental Biology & Embryology (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Breeding Of Plants And Reproduction By Means Of Culturing (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US19367780A | 1980-10-03 | 1980-10-03 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS57102868A JPS57102868A (en) | 1982-06-26 |
| JPH0567625B2 true JPH0567625B2 (en, 2012) | 1993-09-27 |
Family
ID=22714560
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP56156321A Granted JPS57102868A (en) | 1980-10-03 | 1981-10-02 | 1-aryl-1,4-dihydro-4-oxo-5-carboxypyridazine derivative, manufacture and plant growth regulant and use as cross-fertilizing agent |
Country Status (6)
| Country | Link |
|---|---|
| JP (1) | JPS57102868A (en, 2012) |
| KR (1) | KR860001251B1 (en, 2012) |
| AR (1) | AR228965A1 (en, 2012) |
| BR (1) | BR8106381A (en, 2012) |
| CA (1) | CA1275098A (en, 2012) |
| PH (1) | PH20899A (en, 2012) |
-
1981
- 1981-09-21 CA CA000386272A patent/CA1275098A/en not_active Expired
- 1981-09-22 PH PH26243A patent/PH20899A/en unknown
- 1981-09-22 AR AR286838A patent/AR228965A1/es active
- 1981-10-02 BR BR8106381A patent/BR8106381A/pt unknown
- 1981-10-02 KR KR1019810003717A patent/KR860001251B1/ko not_active Expired
- 1981-10-02 JP JP56156321A patent/JPS57102868A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS57102868A (en) | 1982-06-26 |
| CA1275098C (en) | 1990-10-09 |
| KR860001251B1 (ko) | 1986-09-01 |
| AR228965A1 (es) | 1983-05-13 |
| PH20899A (en) | 1987-05-27 |
| CA1275098A (en) | 1990-10-09 |
| BR8106381A (pt) | 1982-06-22 |
| KR830006905A (ko) | 1983-10-12 |
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