DD201639A5 - Pflanzenwachstumsregulierendes mittel - Google Patents
Pflanzenwachstumsregulierendes mittel Download PDFInfo
- Publication number
- DD201639A5 DD201639A5 DD81233895A DD23389581A DD201639A5 DD 201639 A5 DD201639 A5 DD 201639A5 DD 81233895 A DD81233895 A DD 81233895A DD 23389581 A DD23389581 A DD 23389581A DD 201639 A5 DD201639 A5 DD 201639A5
- Authority
- DD
- German Democratic Republic
- Prior art keywords
- dihydro
- oxo
- alkyl
- group
- ethyl
- Prior art date
Links
- 230000008635 plant growth Effects 0.000 title claims abstract description 8
- 230000001105 regulatory effect Effects 0.000 title claims description 7
- 150000001875 compounds Chemical class 0.000 claims description 45
- 239000003795 chemical substances by application Substances 0.000 claims description 16
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 15
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 14
- 239000002253 acid Substances 0.000 claims description 12
- -1 alkali metal salt Chemical class 0.000 claims description 12
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 12
- 239000000203 mixture Substances 0.000 claims description 12
- 239000001257 hydrogen Substances 0.000 claims description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims description 11
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 8
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims description 7
- 229910052700 potassium Inorganic materials 0.000 claims description 6
- 229910052708 sodium Inorganic materials 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000001624 naphthyl group Chemical group 0.000 claims description 4
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- 150000002431 hydrogen Chemical group 0.000 claims 1
- 230000000694 effects Effects 0.000 abstract description 7
- 150000004892 pyridazines Chemical class 0.000 abstract description 5
- 230000008654 plant damage Effects 0.000 abstract description 4
- 230000002411 adverse Effects 0.000 abstract description 2
- 241000196324 Embryophyta Species 0.000 description 22
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- 206010021929 Infertility male Diseases 0.000 description 11
- 208000007466 Male Infertility Diseases 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 10
- 210000005069 ears Anatomy 0.000 description 10
- 238000000921 elemental analysis Methods 0.000 description 10
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 9
- 239000011734 sodium Substances 0.000 description 9
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 8
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 8
- 238000000034 method Methods 0.000 description 8
- 238000005481 NMR spectroscopy Methods 0.000 description 7
- 230000015572 biosynthetic process Effects 0.000 description 7
- ZPSJGADGUYYRKE-UHFFFAOYSA-N 2H-pyran-2-one Chemical compound O=C1C=CC=CO1 ZPSJGADGUYYRKE-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 241000209140 Triticum Species 0.000 description 6
- 235000021307 Triticum Nutrition 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 5
- 239000012346 acetyl chloride Substances 0.000 description 5
- 239000012954 diazonium Substances 0.000 description 5
- 208000000509 infertility Diseases 0.000 description 5
- 230000036512 infertility Effects 0.000 description 5
- 208000021267 infertility disease Diseases 0.000 description 5
- 230000005764 inhibitory process Effects 0.000 description 5
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 5
- 239000002002 slurry Substances 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
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 4
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- 150000001989 diazonium salts Chemical class 0.000 description 4
- 150000005690 diesters Chemical class 0.000 description 4
- 239000012065 filter cake Substances 0.000 description 4
- IUYHWZFSGMZEOG-UHFFFAOYSA-M magnesium;propane;chloride Chemical compound [Mg+2].[Cl-].C[CH-]C IUYHWZFSGMZEOG-UHFFFAOYSA-M 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- 239000001632 sodium acetate Substances 0.000 description 4
- 235000017281 sodium acetate Nutrition 0.000 description 4
- 239000012312 sodium hydride Substances 0.000 description 4
- 229910000104 sodium hydride Inorganic materials 0.000 description 4
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
- 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 3
- OXTNCQMOKLOUAM-UHFFFAOYSA-N 3-Oxoglutaric acid Chemical compound OC(=O)CC(=O)CC(O)=O OXTNCQMOKLOUAM-UHFFFAOYSA-N 0.000 description 3
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- 239000000538 analytical sample Substances 0.000 description 3
- 235000013339 cereals Nutrition 0.000 description 3
- 230000035558 fertility Effects 0.000 description 3
- 229910052744 lithium Inorganic materials 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 239000011591 potassium Substances 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- JUSIWJONLKBPDU-UHFFFAOYSA-N pyridazine-4-carboxylic acid Chemical compound OC(=O)C1=CC=NN=C1 JUSIWJONLKBPDU-UHFFFAOYSA-N 0.000 description 3
- JLYXXMFPNIAWKQ-UHFFFAOYSA-N γ Benzene hexachloride Chemical compound ClC1C(Cl)C(Cl)C(Cl)C(Cl)C1Cl JLYXXMFPNIAWKQ-UHFFFAOYSA-N 0.000 description 3
- WMMUSAGDAKBJKJ-UHFFFAOYSA-N 2,3-dimethyl-5-oxopyridazine-4-carboxylic acid Chemical compound CC1=C(C(O)=O)C(=O)C=NN1C WMMUSAGDAKBJKJ-UHFFFAOYSA-N 0.000 description 2
- 125000006276 2-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C(*)C([H])=C1[H] 0.000 description 2
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 2
- 125000006275 3-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C([H])C(*)=C1[H] 0.000 description 2
- 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 2
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 description 2
- 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 2
- 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 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
- 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 2
- 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 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 206010021928 Infertility female Diseases 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
- 231100000674 Phytotoxicity Toxicity 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
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 2
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 230000001276 controlling effect Effects 0.000 description 2
- 235000005822 corn Nutrition 0.000 description 2
- 238000006114 decarboxylation reaction Methods 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 239000003337 fertilizer Substances 0.000 description 2
- 125000005059 halophenyl group Chemical group 0.000 description 2
- 150000007857 hydrazones Chemical class 0.000 description 2
- 230000001976 improved effect Effects 0.000 description 2
- 239000010410 layer Substances 0.000 description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000005648 plant growth regulator Substances 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 235000010288 sodium nitrite Nutrition 0.000 description 2
- GDZMROPWAPWWQI-UHFFFAOYSA-M sodium;1-(4-chlorophenyl)-6-methyl-4-oxopyridazine-3-carboxylate Chemical compound [Na+].CC1=CC(=O)C(C([O-])=O)=NN1C1=CC=C(Cl)C=C1 GDZMROPWAPWWQI-UHFFFAOYSA-M 0.000 description 2
- 238000000967 suction filtration Methods 0.000 description 2
- 239000004094 surface-active agent Substances 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
- 239000008096 xylene Substances 0.000 description 2
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 description 1
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 description 1
- HZCRNYJMUIULKA-UHFFFAOYSA-N 1-(3-ethoxyphenyl)-6-ethyl-4-oxopyridazine-3,5-dicarboxylic acid Chemical compound CCOC1=CC=CC(N2C(=C(C(O)=O)C(=O)C(C(O)=O)=N2)CC)=C1 HZCRNYJMUIULKA-UHFFFAOYSA-N 0.000 description 1
- FDYLFPBSVMZKGR-UHFFFAOYSA-N 1-(4-methylphenyl)-4-oxo-6-phenylpyridazine-3,5-dicarboxylic acid Chemical compound C1=CC(C)=CC=C1N1C(C=2C=CC=CC=2)=C(C(O)=O)C(=O)C(C(O)=O)=N1 FDYLFPBSVMZKGR-UHFFFAOYSA-N 0.000 description 1
- PWMWNFMRSKOCEY-UHFFFAOYSA-N 1-Phenyl-1,2-ethanediol Chemical compound OCC(O)C1=CC=CC=C1 PWMWNFMRSKOCEY-UHFFFAOYSA-N 0.000 description 1
- QPLAXQUTZKEEED-UHFFFAOYSA-N 1-[4-bromo-2-(trifluoromethyl)phenyl]-6-ethyl-4-oxopyridazine-3,5-dicarboxylic acid Chemical compound CCC1=C(C(O)=O)C(=O)C(C(O)=O)=NN1C1=CC=C(Br)C=C1C(F)(F)F QPLAXQUTZKEEED-UHFFFAOYSA-N 0.000 description 1
- LBDYXXQOMXQXOR-UHFFFAOYSA-N 1-[4-chloro-2-(trifluoromethyl)phenyl]-6-methyl-4-oxopyridazine-3,5-dicarboxylic acid Chemical compound CC1=C(C(O)=O)C(=O)C(C(O)=O)=NN1C1=CC=C(Cl)C=C1C(F)(F)F LBDYXXQOMXQXOR-UHFFFAOYSA-N 0.000 description 1
- VXZCDXKDYTTYQH-UHFFFAOYSA-N 1-butyl-6-methyl-4-oxopyridazine-3,5-dicarboxylic acid Chemical compound CCCCN1N=C(C(O)=O)C(=O)C(C(O)=O)=C1C VXZCDXKDYTTYQH-UHFFFAOYSA-N 0.000 description 1
- MZPKYLMDUBSTST-UHFFFAOYSA-N 1-methyl-4-oxo-6-propylpyridazine-3,5-dicarboxylic acid Chemical compound CCCC1=C(C(O)=O)C(=O)C(C(O)=O)=NN1C MZPKYLMDUBSTST-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
- 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
- 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
- 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
- XQWWZVGJBWVPGW-UHFFFAOYSA-N 2-butyl-5-oxo-3-propylpyridazine-4-carboxylic acid Chemical compound CCCCN1N=CC(=O)C(C(O)=O)=C1CCC XQWWZVGJBWVPGW-UHFFFAOYSA-N 0.000 description 1
- APJJFFLZXPRVNB-UHFFFAOYSA-N 3-butyl-2-(4-fluorophenyl)-5-oxopyridazine-4-carboxylic acid Chemical compound CCCCC1=C(C(O)=O)C(=O)C=NN1C1=CC=C(F)C=C1 APJJFFLZXPRVNB-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
- 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
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 1
- 125000006306 4-iodophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1I 0.000 description 1
- 125000004199 4-trifluoromethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C(F)(F)F 0.000 description 1
- NVHFVDZJOQCVQN-UHFFFAOYSA-N 6-benzyl-4-oxo-1-(2,4,6-trichlorophenyl)pyridazine-3,5-dicarboxylic acid Chemical compound OC(=O)C=1C(=O)C(C(=O)O)=NN(C=2C(=CC(Cl)=CC=2Cl)Cl)C=1CC1=CC=CC=C1 NVHFVDZJOQCVQN-UHFFFAOYSA-N 0.000 description 1
- SHMBVZIRYGQYLR-UHFFFAOYSA-N 6-butyl-1-(3-cyanophenyl)-4-oxopyridazine-3,5-dicarboxylic acid Chemical compound CCCCC1=C(C(O)=O)C(=O)C(C(O)=O)=NN1C1=CC=CC(C#N)=C1 SHMBVZIRYGQYLR-UHFFFAOYSA-N 0.000 description 1
- ACNFXJRGGAPSHF-UHFFFAOYSA-N 6-butyl-1-naphthalen-2-yl-4-oxopyridazine-3,5-dicarboxylic acid Chemical compound CCCCC1=C(C(O)=O)C(=O)C(C(O)=O)=NN1C1=CC=C(C=CC=C2)C2=C1 ACNFXJRGGAPSHF-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 241001124076 Aphididae Species 0.000 description 1
- 235000007319 Avena orientalis Nutrition 0.000 description 1
- 244000075850 Avena orientalis Species 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 229940126062 Compound A Drugs 0.000 description 1
- 241000221785 Erysiphales Species 0.000 description 1
- 208000007984 Female Infertility Diseases 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 1
- 240000005979 Hordeum vulgare Species 0.000 description 1
- 235000007340 Hordeum vulgare Nutrition 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical class O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 240000007594 Oryza sativa Species 0.000 description 1
- 235000007164 Oryza sativa Nutrition 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 241000209056 Secale Species 0.000 description 1
- 235000007238 Secale cereale Nutrition 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
- 150000007513 acids Chemical class 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000008135 aqueous vehicle Substances 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 150000001733 carboxylic acid esters Chemical class 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- NUUZKOFSZIWYSC-UHFFFAOYSA-M clofencet-potassium Chemical compound [K+].CCC1=C(C([O-])=O)C(=O)C=NN1C1=CC=C(Cl)C=C1 NUUZKOFSZIWYSC-UHFFFAOYSA-M 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000013068 control sample Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000009402 cross-breeding Methods 0.000 description 1
- 230000010154 cross-pollination Effects 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical compound [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 description 1
- 239000003085 diluting agent 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
- 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
- 238000011038 discontinuous diafiltration by volume reduction Methods 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 230000004883 flower formation Effects 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 231100000722 genetic damage Toxicity 0.000 description 1
- 239000012456 homogeneous solution Substances 0.000 description 1
- 239000003864 humus Substances 0.000 description 1
- 238000009396 hybridization Methods 0.000 description 1
- 230000036571 hydration Effects 0.000 description 1
- 238000006703 hydration reaction Methods 0.000 description 1
- 238000002513 implantation Methods 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 230000035800 maturation Effects 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
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 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
- NQBKFULMFQMZBE-UHFFFAOYSA-N n-bz-3-benzanthronylpyrazolanthron Chemical compound C12=CC=CC(C(=O)C=3C4=CC=CC=3)=C2C4=NN1C1=CC=C2C3=C1C1=CC=CC=C1C(=O)C3=CC=C2 NQBKFULMFQMZBE-UHFFFAOYSA-N 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- 230000010152 pollination Effects 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 1
- RDQWJNPUOHXYCV-UHFFFAOYSA-N pyridazine-3,4-dicarboxylic acid Chemical compound 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
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000006748 scratching Methods 0.000 description 1
- 230000002393 scratching effect Effects 0.000 description 1
- 210000000582 semen Anatomy 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- MVWUBJGLGGZKGG-UHFFFAOYSA-M sodium;2-(4-chlorophenyl)-3-methyl-5-oxopyridazine-4-carboxylate Chemical compound [Na+].CC1=C(C([O-])=O)C(=O)C=NN1C1=CC=C(Cl)C=C1 MVWUBJGLGGZKGG-UHFFFAOYSA-M 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000009331 sowing Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 125000004953 trihalomethyl group Chemical group 0.000 description 1
- GPRLSGONYQIRFK-MNYXATJNSA-N triton Chemical group [3H+] GPRLSGONYQIRFK-MNYXATJNSA-N 0.000 description 1
- 238000005292 vacuum distillation Methods 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
Classifications
-
- 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
- A01H1/022—Genic fertility modification, e.g. apomixis
- A01H1/023—Male sterility
-
- 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)
- Environmental Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Developmental Biology & Embryology (AREA)
- Botany (AREA)
- Genetics & Genomics (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Plant Pathology (AREA)
- Zoology (AREA)
- Wood Science & Technology (AREA)
- Dentistry (AREA)
- Engineering & Computer Science (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Plural Heterocyclic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US19367280A | 1980-10-03 | 1980-10-03 | |
| US19367780A | 1980-10-03 | 1980-10-03 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DD201639A5 true DD201639A5 (de) | 1983-08-03 |
Family
ID=26889226
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD81233895A DD201639A5 (de) | 1980-10-03 | 1981-10-05 | Pflanzenwachstumsregulierendes mittel |
Country Status (11)
| Country | Link |
|---|---|
| EP (1) | EP0049971B1 (fr) |
| AU (1) | AU549931B2 (fr) |
| DD (1) | DD201639A5 (fr) |
| DE (1) | DE3176084D1 (fr) |
| DK (2) | DK154835C (fr) |
| EG (1) | EG15679A (fr) |
| ES (2) | ES8305556A1 (fr) |
| GR (1) | GR75799B (fr) |
| IL (1) | IL64039A (fr) |
| NZ (1) | NZ198485A (fr) |
| PT (1) | PT73766B (fr) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DK154836C (da) * | 1982-03-04 | 1989-05-16 | Ici Plc | Substituerede pyridaziner, deres anvendelse som plantevaekstreguleringsmidler og plantevaekstreguleringsmidler, der indeholder dem |
| US4623378A (en) * | 1983-08-10 | 1986-11-18 | Ciba-Geigy Corporation | Gametocidal pyridazinylcarboxylic acid derivatives |
| US4666504A (en) * | 1984-09-25 | 1987-05-19 | Eli Lilly And Company | Pollen formation inhibiting 1-phenyl-4-carboxy-5-pyrazolecarboxamides |
| GB8821447D0 (en) * | 1988-09-13 | 1988-10-12 | Ici Plc | Pyridazinone manufacture |
| GB8821448D0 (en) * | 1988-09-13 | 1988-10-12 | Ici Plc | Pyridazinone manufacture |
| GB8821449D0 (en) * | 1988-09-13 | 1988-10-12 | Ici Plc | Pyridazinone manufacture |
| US5189163A (en) * | 1989-08-30 | 1993-02-23 | Imperial Chemical Industries Plc | Method of preparing pyridazinone derivatives |
| GB8919622D0 (en) * | 1989-08-30 | 1989-10-11 | Ici Plc | A method of preparing pyridazinone derivatives |
| EP1149108A1 (fr) | 1999-02-02 | 2001-10-31 | Monsanto Co. | Production de phosphonopyrazoles |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PL115813B1 (en) * | 1977-03-10 | 1981-05-30 | Plant growth regulator |
-
1981
- 1981-09-28 GR GR66140A patent/GR75799B/el unknown
- 1981-09-29 NZ NZ198485A patent/NZ198485A/en unknown
- 1981-09-29 DE DE8181304487T patent/DE3176084D1/de not_active Expired
- 1981-09-29 EP EP81304487A patent/EP0049971B1/fr not_active Expired
- 1981-09-30 DK DK434181A patent/DK154835C/da not_active IP Right Cessation
- 1981-10-02 PT PT73766A patent/PT73766B/pt unknown
- 1981-10-02 ES ES505995A patent/ES8305556A1/es not_active Expired
- 1981-10-02 AU AU75992/81A patent/AU549931B2/en not_active Expired
- 1981-10-03 EG EG569/81A patent/EG15679A/xx active
- 1981-10-05 DD DD81233895A patent/DD201639A5/de unknown
- 1981-10-12 IL IL64039A patent/IL64039A/xx not_active IP Right Cessation
-
1982
- 1982-08-09 ES ES514867A patent/ES514867A0/es active Granted
-
1988
- 1988-07-13 DK DK391688A patent/DK158247C/da not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| IL64039A0 (en) | 1982-01-31 |
| ES505995A0 (es) | 1983-04-16 |
| AU7599281A (en) | 1982-04-08 |
| EP0049971A1 (fr) | 1982-04-21 |
| AU549931B2 (en) | 1986-02-20 |
| DK158247B (da) | 1990-04-23 |
| PT73766B (en) | 1983-10-14 |
| DK154835C (da) | 1989-06-05 |
| PT73766A (en) | 1981-11-01 |
| ES8305556A1 (es) | 1983-04-16 |
| IL64039A (en) | 1986-04-29 |
| NZ198485A (en) | 1985-07-31 |
| DK154835B (da) | 1988-12-27 |
| DK434181A (da) | 1982-04-04 |
| GR75799B (fr) | 1984-08-02 |
| EG15679A (en) | 1986-12-30 |
| DE3176084D1 (en) | 1987-05-14 |
| ES8401039A1 (es) | 1983-12-01 |
| DK391688A (da) | 1988-07-13 |
| ES514867A0 (es) | 1983-12-01 |
| EP0049971B1 (fr) | 1987-04-08 |
| DK158247C (da) | 1990-10-08 |
| DK391688D0 (da) | 1988-07-13 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE2654890A1 (de) | 1,2,4-triazolverbindungen und diese verbindungen enthaltende fungizide mittel | |
| US4936904A (en) | Aryl-4-oxonicotinates useful for inducing male sterility in cereal grain plants | |
| DE2858755C2 (fr) | ||
| DE2723376C2 (fr) | ||
| DE69334162T2 (de) | Heteroaroyl-isoxazole und ihre Verwendung als Herbizide | |
| DD201639A5 (de) | Pflanzenwachstumsregulierendes mittel | |
| DE2734426A1 (de) | Zusammensetzung und verfahren zur bekaempfung von pilzen | |
| EP0177450B1 (fr) | Procédé de préparation de dérivés d'acides cyclohexanedionecarboxyliques ayant une activité herbicide et régulatrice pour la croissance des plantes | |
| DE2830700C2 (fr) | ||
| US4732603A (en) | 1-aryl-1,4-dihydro-4-oxo-5-carboxypyridazine derivatives and their use as plant growth regulators and hybridizing agents | |
| EP0136974A2 (fr) | Dérivés d'acide pyridazinylcarboxylique à activité gamétocide | |
| GB2145085A (en) | Herbicidal 2-and/or 6-fluoromethyl-dihydropyridine-3,5-dicarboxylic acid esters | |
| DE3422346A1 (de) | Neue herbizid wirksame 5-amino-3-oxo-4-(subst.-phenyl)-2,3-dihydrofurane und derivate davon, verfahren zu ihrer herstellung sowie diese verbindungen enthaltende herbizide mittel | |
| US4707181A (en) | 1-aryl-1,4-dihydro-4-oxo-3,5-dicarboxypyridazine derivatives and their use as plant growth regulators and hybridizing agents | |
| DE3016304C2 (fr) | ||
| EP0143281B1 (fr) | Pyridazines substituées, leur procédé de péparation, leur usage comme régulateurs de croissance des plantes et compositions régulatrices de croissance des plantes les contenant | |
| DE2647195A1 (de) | Verfahren zur steuerung des pflanzenwachstums | |
| US4714492A (en) | Certain 2-phenyl-4-oxo-nicotinates and their use for inducing male sterility in a cereal grain plant | |
| CH627477A5 (de) | Verfahren zur herstellung einer neuen phosphinsaeure und ihrer salze. | |
| DD139788A5 (de) | Pflanzenwuchsregulierende mittel | |
| EP0364135B1 (fr) | Hybridation chimique des dicotylédones | |
| DE3820538A1 (de) | Substituierte 3-(pyridylcarbonyl-aza-, -oxa- und thiacyclohex-5-en-2,4-dione, ihre benzo (b) - oder 5,6-dihydroderivate, herstellung und ihre verwendung als herbizid | |
| US5062880A (en) | 1-aryl-1,4-dihydro-4-oxo-5-carboxypyridazine derivatives and their use as plant growth regulators and hybridizing agents | |
| DE2154634A1 (fr) | ||
| PL160261B1 (pl) | Srodek chwastobójczy PL PL |