NZ203401A - Substituted pyridazine derivatives and plant growth regulating compositions - Google Patents
Substituted pyridazine derivatives and plant growth regulating compositionsInfo
- Publication number
- NZ203401A NZ203401A NZ203401A NZ20340183A NZ203401A NZ 203401 A NZ203401 A NZ 203401A NZ 203401 A NZ203401 A NZ 203401A NZ 20340183 A NZ20340183 A NZ 20340183A NZ 203401 A NZ203401 A NZ 203401A
- Authority
- NZ
- New Zealand
- Prior art keywords
- alkyl
- ethyl
- phenyl
- plant
- ona
- Prior art date
Links
- 230000001105 regulatory effect Effects 0.000 title claims abstract description 18
- 230000008635 plant growth Effects 0.000 title claims abstract description 10
- 239000000203 mixture Substances 0.000 title claims description 31
- 150000004892 pyridazines Chemical class 0.000 title abstract description 7
- 150000001875 compounds Chemical class 0.000 claims abstract description 77
- 150000003839 salts Chemical class 0.000 claims abstract description 32
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 27
- 239000002253 acid Substances 0.000 claims abstract description 14
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 11
- 239000001257 hydrogen Substances 0.000 claims abstract description 11
- 125000001424 substituent group Chemical group 0.000 claims abstract description 10
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 9
- 150000002367 halogens Chemical class 0.000 claims abstract description 9
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 8
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 7
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 7
- 150000003863 ammonium salts Chemical class 0.000 claims abstract description 6
- 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
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 5
- 229910052751 metal Inorganic materials 0.000 claims abstract description 5
- 239000002184 metal Substances 0.000 claims abstract description 5
- 125000001453 quaternary ammonium group Chemical group 0.000 claims abstract description 5
- 125000004953 trihalomethyl group Chemical group 0.000 claims abstract description 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 4
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims abstract description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 3
- 125000001624 naphthyl group Chemical group 0.000 claims abstract description 3
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims abstract 4
- 125000000217 alkyl group Chemical group 0.000 claims description 50
- 241000196324 Embryophyta Species 0.000 claims description 32
- -1 alkali metal cation Chemical class 0.000 claims description 32
- 238000000034 method Methods 0.000 claims description 19
- 206010021929 Infertility male Diseases 0.000 claims description 16
- 208000007466 Male Infertility Diseases 0.000 claims description 16
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 16
- 230000005764 inhibitory process Effects 0.000 claims description 11
- 208000027418 Wounds and injury Diseases 0.000 claims description 10
- 239000003795 chemical substances by application Substances 0.000 claims description 10
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- 208000014674 injury Diseases 0.000 claims description 10
- 235000021307 Triticum Nutrition 0.000 claims description 9
- 241000209140 Triticum Species 0.000 claims description 9
- 229910052783 alkali metal Inorganic materials 0.000 claims description 9
- 230000012010 growth Effects 0.000 claims description 8
- 150000002148 esters Chemical class 0.000 claims description 7
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 6
- 239000003085 diluting agent Substances 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 5
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 5
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 4
- 230000035558 fertility Effects 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims description 3
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 claims description 3
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 3
- 125000006306 4-iodophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1I 0.000 claims description 3
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 3
- 240000005979 Hordeum vulgare Species 0.000 claims description 3
- 235000007340 Hordeum vulgare Nutrition 0.000 claims description 3
- 240000008042 Zea mays Species 0.000 claims description 3
- 235000002017 Zea mays subsp mays Nutrition 0.000 claims description 3
- 150000001340 alkali metals Chemical group 0.000 claims description 3
- 230000015572 biosynthetic process Effects 0.000 claims description 3
- 229910052794 bromium Inorganic materials 0.000 claims description 3
- 229910052731 fluorine Inorganic materials 0.000 claims description 3
- 229910052740 iodine Inorganic materials 0.000 claims description 3
- 230000021121 meiosis Effects 0.000 claims description 3
- 125000004199 4-trifluoromethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C(F)(F)F 0.000 claims description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 2
- 240000006394 Sorghum bicolor Species 0.000 claims description 2
- 235000011684 Sorghum saccharatum Nutrition 0.000 claims description 2
- 235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 claims description 2
- 150000001768 cations Chemical class 0.000 claims description 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 2
- 239000004459 forage Substances 0.000 claims description 2
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 2
- 235000009973 maize Nutrition 0.000 claims description 2
- 244000038559 crop plants Species 0.000 claims 3
- 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 claims 1
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims 1
- 125000006275 3-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C([H])C(*)=C1[H] 0.000 claims 1
- 125000003262 carboxylic acid ester group Chemical group [H]C([H])([*:2])OC(=O)C([H])([H])[*:1] 0.000 claims 1
- 125000000068 chlorophenyl group Chemical group 0.000 claims 1
- 125000004185 ester group Chemical group 0.000 claims 1
- 125000001475 halogen functional group Chemical group 0.000 claims 1
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract description 11
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 2
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 abstract 2
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 abstract 1
- 230000001747 exhibiting effect Effects 0.000 abstract 1
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 78
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 35
- 239000011734 sodium Substances 0.000 description 29
- 239000000243 solution Substances 0.000 description 26
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 24
- 239000000725 suspension Substances 0.000 description 20
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 18
- 239000004480 active ingredient Substances 0.000 description 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- 238000002360 preparation method Methods 0.000 description 14
- 229910052708 sodium Inorganic materials 0.000 description 12
- 125000001309 chloro group Chemical group Cl* 0.000 description 11
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 10
- 239000012065 filter cake Substances 0.000 description 10
- RUUOPSRRIKJHNH-UHFFFAOYSA-N pyridazine-3-carboxylic acid Chemical compound OC(=O)C1=CC=CN=N1 RUUOPSRRIKJHNH-UHFFFAOYSA-N 0.000 description 10
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 9
- 239000012141 concentrate Substances 0.000 description 9
- 235000008504 concentrate Nutrition 0.000 description 9
- 238000000921 elemental analysis Methods 0.000 description 9
- 229910052700 potassium Inorganic materials 0.000 description 9
- 239000000126 substance Substances 0.000 description 9
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 8
- 229960004132 diethyl ether Drugs 0.000 description 8
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 8
- 239000005648 plant growth regulator Substances 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
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- AAILEWXSEQLMNI-UHFFFAOYSA-N 1h-pyridazin-6-one Chemical class OC1=CC=CN=N1 AAILEWXSEQLMNI-UHFFFAOYSA-N 0.000 description 4
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- 238000012360 testing method Methods 0.000 description 4
- DIKVSRSSTOSGSN-UHFFFAOYSA-N 1-(4-chlorophenyl)-6-ethyl-4-oxo-5-propanoylpyridazine-3-carboxylic acid Chemical compound N1=C(C(O)=O)C(=O)C(C(=O)CC)=C(CC)N1C1=CC=C(Cl)C=C1 DIKVSRSSTOSGSN-UHFFFAOYSA-N 0.000 description 3
- QSNSCYSYFYORTR-UHFFFAOYSA-N 4-chloroaniline Chemical compound NC1=CC=C(Cl)C=C1 QSNSCYSYFYORTR-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
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- JDKDYNWDHOJRGJ-UHFFFAOYSA-N 1-(4-bromophenyl)-6-ethyl-4-oxo-5-propanoylpyridazine-3-carboxylic acid Chemical compound N1=C(C(O)=O)C(=O)C(C(=O)CC)=C(CC)N1C1=CC=C(Br)C=C1 JDKDYNWDHOJRGJ-UHFFFAOYSA-N 0.000 description 2
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- 229910052801 chlorine Inorganic materials 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
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 239000004062 cytokinin Substances 0.000 description 1
- UQHKFADEQIVWID-UHFFFAOYSA-N cytokinin Natural products C1=NC=2C(NCC=C(CO)C)=NC=NC=2N1C1CC(O)C(CO)O1 UQHKFADEQIVWID-UHFFFAOYSA-N 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- 125000005265 dialkylamine group Chemical group 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- WPUMTJGUQUYPIV-JIZZDEOASA-L disodium (S)-malate Chemical compound [Na+].[Na+].[O-]C(=O)[C@@H](O)CC([O-])=O WPUMTJGUQUYPIV-JIZZDEOASA-L 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000001035 drying Methods 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
- 238000002474 experimental method Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 239000003448 gibberellin Substances 0.000 description 1
- IXORZMNAPKEEDV-OBDJNFEBSA-N gibberellin A3 Chemical class C([C@@]1(O)C(=C)C[C@@]2(C1)[C@H]1C(O)=O)C[C@H]2[C@]2(C=C[C@@H]3O)[C@H]1[C@]3(C)C(=O)O2 IXORZMNAPKEEDV-OBDJNFEBSA-N 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 230000009036 growth inhibition Effects 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- DGCTVLNZTFDPDJ-UHFFFAOYSA-N heptane-3,5-dione Chemical compound CCC(=O)CC(=O)CC DGCTVLNZTFDPDJ-UHFFFAOYSA-N 0.000 description 1
- 230000002363 herbicidal effect Effects 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 239000003864 humus Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 description 1
- 229940071826 hydroxyethyl cellulose Drugs 0.000 description 1
- 150000007529 inorganic bases Chemical class 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
- 150000002576 ketones Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 235000014666 liquid concentrate Nutrition 0.000 description 1
- 239000006193 liquid solution Substances 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- IIRRCPIBXKQFMT-UHFFFAOYSA-N methyl 6-ethyl-4-oxo-1-phenyl-5-propanoylpyridazine-3-carboxylate Chemical compound N1=C(C(=O)OC)C(=O)C(C(=O)CC)=C(CC)N1C1=CC=CC=C1 IIRRCPIBXKQFMT-UHFFFAOYSA-N 0.000 description 1
- 229940102396 methyl bromide Drugs 0.000 description 1
- 229920003087 methylethyl cellulose Polymers 0.000 description 1
- 235000019713 millet Nutrition 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- ZDYWPVCQPUPOJV-UHFFFAOYSA-N nonane-4,6-dione Chemical compound CCCC(=O)CC(=O)CCC ZDYWPVCQPUPOJV-UHFFFAOYSA-N 0.000 description 1
- 150000002891 organic anions Chemical group 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 238000009401 outcrossing Methods 0.000 description 1
- 230000008654 plant damage Effects 0.000 description 1
- 230000010152 pollination Effects 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
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical class OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000011541 reaction mixture Substances 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
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- LNEPAQBLGYVYMS-UHFFFAOYSA-M sodium;1-(4-bromophenyl)-6-ethyl-4-oxo-5-propanoylpyridazine-3-carboxylate Chemical compound [Na+].N1=C(C([O-])=O)C(=O)C(C(=O)CC)=C(CC)N1C1=CC=C(Br)C=C1 LNEPAQBLGYVYMS-UHFFFAOYSA-M 0.000 description 1
- FVUKJQKLOJLKMV-UHFFFAOYSA-M sodium;1-(4-chlorophenyl)-6-ethyl-4-oxo-5-propanoylpyridazine-3-carboxylate Chemical compound [Na+].N1=C(C([O-])=O)C(=O)C(C(=O)CC)=C(CC)N1C1=CC=C(Cl)C=C1 FVUKJQKLOJLKMV-UHFFFAOYSA-M 0.000 description 1
- MILYTNPSYZUUSR-UHFFFAOYSA-M sodium;5-butanoyl-1-(4-chlorophenyl)-4-oxo-6-propylpyridazine-3-carboxylate Chemical compound [Na+].N1=C(C([O-])=O)C(=O)C(C(=O)CCC)=C(CCC)N1C1=CC=C(Cl)C=C1 MILYTNPSYZUUSR-UHFFFAOYSA-M 0.000 description 1
- 241000894007 species Species 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
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 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
- 238000010998 test method Methods 0.000 description 1
- 239000012085 test solution Substances 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
- 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
- 235000019354 vermiculite Nutrition 0.000 description 1
- 229910052902 vermiculite Inorganic materials 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
- 241000228158 x Triticosecale Species 0.000 description 1
- 239000008096 xylene Substances 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
- A01H3/00—Processes for modifying phenotypes, e.g. symbiosis with bacteria
- A01H3/04—Processes for modifying phenotypes, e.g. symbiosis with bacteria 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
- 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
-
- 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 Chemical & Material Sciences (AREA)
- Developmental Biology & Embryology (AREA)
- Botany (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Genetics & Genomics (AREA)
- Agronomy & Crop Science (AREA)
- Zoology (AREA)
- Engineering & Computer Science (AREA)
- Pest Control & Pesticides (AREA)
- Dentistry (AREA)
- Plant Pathology (AREA)
- Wood Science & Technology (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Breeding Of Plants And Reproduction By Means Of Culturing (AREA)
- Liquid Crystal Substances (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US35484582A | 1982-03-04 | 1982-03-04 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NZ203401A true NZ203401A (en) | 1985-09-13 |
Family
ID=23395138
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NZ203401A NZ203401A (en) | 1982-03-04 | 1983-02-25 | Substituted pyridazine derivatives and plant growth regulating compositions |
Country Status (17)
| Country | Link |
|---|---|
| EP (1) | EP0089137B1 (en, 2012) |
| JP (1) | JPS58162578A (en, 2012) |
| KR (1) | KR840003770A (en, 2012) |
| AT (1) | ATE23526T1 (en, 2012) |
| AU (1) | AU562778B2 (en, 2012) |
| BR (1) | BR8301052A (en, 2012) |
| CA (1) | CA1276149C (en, 2012) |
| DE (1) | DE3367590D1 (en, 2012) |
| DK (1) | DK154836C (en, 2012) |
| EG (1) | EG16250A (en, 2012) |
| ES (2) | ES520269A0 (en, 2012) |
| GR (1) | GR78472B (en, 2012) |
| IL (1) | IL68012A (en, 2012) |
| NZ (1) | NZ203401A (en, 2012) |
| OA (1) | OA07336A (en, 2012) |
| PT (1) | PT76301B (en, 2012) |
| ZA (1) | ZA831338B (en, 2012) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3056384A (en) * | 1957-05-07 | 1962-10-02 | Mccorquodale Colour Display | Apparatus for the deposition of liquid materials |
| US4623378A (en) * | 1983-08-10 | 1986-11-18 | Ciba-Geigy Corporation | Gametocidal pyridazinylcarboxylic acid derivatives |
| GB8821447D0 (en) * | 1988-09-13 | 1988-10-12 | Ici Plc | Pyridazinone manufacture |
| JP2007234404A (ja) * | 2006-03-01 | 2007-09-13 | Fujitsu Ltd | コネクタの抜け防止装置およびコネクタの抜け防止部品 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PL115813B1 (en) * | 1977-03-10 | 1981-05-30 | Plant growth regulator | |
| 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 |
| EP0037134A1 (en) * | 1980-03-26 | 1981-10-07 | Shell Internationale Researchmaatschappij B.V. | Pyridazine derivatives, process for their preparation, compositions containing them and methods 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 (en, 2012) * | 1980-10-03 | 1984-08-02 | Ici Plc |
-
1983
- 1983-02-14 DK DK063483A patent/DK154836C/da not_active IP Right Cessation
- 1983-02-18 CA CA000421956A patent/CA1276149C/en not_active Expired - Lifetime
- 1983-02-25 NZ NZ203401A patent/NZ203401A/en unknown
- 1983-02-28 AT AT83301057T patent/ATE23526T1/de not_active IP Right Cessation
- 1983-02-28 PT PT76301A patent/PT76301B/pt unknown
- 1983-02-28 ZA ZA831338A patent/ZA831338B/xx unknown
- 1983-02-28 DE DE8383301057T patent/DE3367590D1/de not_active Expired
- 1983-02-28 EP EP83301057A patent/EP0089137B1/en not_active Expired
- 1983-02-28 GR GR70625A patent/GR78472B/el unknown
- 1983-03-01 IL IL68012A patent/IL68012A/xx not_active IP Right Cessation
- 1983-03-01 AU AU11939/83A patent/AU562778B2/en not_active Ceased
- 1983-03-03 ES ES520269A patent/ES520269A0/es active Granted
- 1983-03-03 BR BR8301052A patent/BR8301052A/pt unknown
- 1983-03-04 JP JP58034678A patent/JPS58162578A/ja active Granted
- 1983-03-04 KR KR1019830000873A patent/KR840003770A/ko not_active Withdrawn
- 1983-03-04 OA OA57930A patent/OA07336A/xx unknown
- 1983-03-05 EG EG145/83A patent/EG16250A/xx active
-
1984
- 1984-05-30 ES ES532953A patent/ES532953A0/es active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| DK63483A (da) | 1983-09-05 |
| PT76301A (en) | 1983-03-01 |
| KR840003770A (ko) | 1984-10-04 |
| ES8407480A1 (es) | 1984-10-01 |
| DK154836C (da) | 1989-05-16 |
| DK63483D0 (da) | 1983-02-14 |
| IL68012A0 (en) | 1983-06-15 |
| CA1276149C (en) | 1990-11-13 |
| EP0089137A1 (en) | 1983-09-21 |
| DK154836B (da) | 1988-12-27 |
| ATE23526T1 (de) | 1986-11-15 |
| JPH0559111B2 (en, 2012) | 1993-08-30 |
| GR78472B (en, 2012) | 1984-09-27 |
| AU562778B2 (en) | 1987-06-18 |
| OA07336A (fr) | 1984-08-31 |
| ZA831338B (en) | 1984-04-25 |
| JPS58162578A (ja) | 1983-09-27 |
| EG16250A (en) | 1987-03-30 |
| DE3367590D1 (en) | 1987-01-02 |
| BR8301052A (pt) | 1983-11-22 |
| AU1193983A (en) | 1983-09-08 |
| ES8503230A1 (es) | 1985-02-16 |
| ES520269A0 (es) | 1984-10-01 |
| PT76301B (en) | 1986-06-18 |
| ES532953A0 (es) | 1985-02-16 |
| IL68012A (en) | 1986-12-31 |
| EP0089137B1 (en) | 1986-11-12 |
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