ZA200106071B - Production of phosphonopyrazoles. - Google Patents
Production of phosphonopyrazoles. Download PDFInfo
- Publication number
- ZA200106071B ZA200106071B ZA200106071A ZA200106071A ZA200106071B ZA 200106071 B ZA200106071 B ZA 200106071B ZA 200106071 A ZA200106071 A ZA 200106071A ZA 200106071 A ZA200106071 A ZA 200106071A ZA 200106071 B ZA200106071 B ZA 200106071B
- Authority
- ZA
- South Africa
- Prior art keywords
- pyrazol
- alkyl
- group
- dimethyl
- phosphonate
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title claims description 19
- VISXMJCAAVEDDT-UHFFFAOYSA-N 1h-pyrazol-5-ylphosphonic acid Chemical class OP(O)(=O)C=1C=CNN=1 VISXMJCAAVEDDT-UHFFFAOYSA-N 0.000 title claims description 9
- 239000000203 mixture Substances 0.000 claims description 61
- 150000001875 compounds Chemical class 0.000 claims description 57
- 241000196324 Embryophyta Species 0.000 claims description 50
- 125000000217 alkyl group Chemical group 0.000 claims description 48
- 238000000034 method Methods 0.000 claims description 48
- 229910052739 hydrogen Inorganic materials 0.000 claims description 43
- 239000001257 hydrogen Substances 0.000 claims description 43
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims description 39
- -1 protonated alkyl hydrazine Chemical compound 0.000 claims description 31
- 125000003118 aryl group Chemical group 0.000 claims description 30
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 30
- 150000003839 salts Chemical class 0.000 claims description 30
- 150000002431 hydrogen Chemical class 0.000 claims description 29
- 125000001072 heteroaryl group Chemical group 0.000 claims description 28
- 125000003545 alkoxy group Chemical group 0.000 claims description 26
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 25
- 229910052736 halogen Inorganic materials 0.000 claims description 25
- 150000002367 halogens Chemical class 0.000 claims description 25
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 25
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 25
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 23
- 125000004953 trihalomethyl group Chemical group 0.000 claims description 23
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 claims description 19
- 230000008569 process Effects 0.000 claims description 19
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 14
- 206010021929 Infertility male Diseases 0.000 claims description 12
- 208000007466 Male Infertility Diseases 0.000 claims description 12
- 125000001624 naphthyl group Chemical group 0.000 claims description 11
- 125000004076 pyridyl group Chemical group 0.000 claims description 11
- 241000209140 Triticum Species 0.000 claims description 10
- OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine Substances NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 8
- 239000003960 organic solvent Substances 0.000 claims description 8
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 7
- 239000003125 aqueous solvent Substances 0.000 claims description 7
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 6
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 claims description 6
- 159000000011 group IA salts Chemical class 0.000 claims description 6
- 230000001939 inductive effect Effects 0.000 claims description 6
- 125000003342 alkenyl group Chemical group 0.000 claims description 5
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 4
- 241000209510 Liliopsida Species 0.000 claims description 4
- BHGADZKHWXCHKX-UHFFFAOYSA-N methane;potassium Chemical compound C.[K] BHGADZKHWXCHKX-UHFFFAOYSA-N 0.000 claims description 4
- 230000020477 pH reduction Effects 0.000 claims description 4
- 125000001476 phosphono group Chemical group [H]OP(*)(=O)O[H] 0.000 claims description 4
- 125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 claims description 3
- KLIWMKCTBFKERB-UHFFFAOYSA-N OC1=C(P(=O)(OC)OC)C=NN1C1=CC=C(Cl)C=C1 Chemical compound OC1=C(P(=O)(OC)OC)C=NN1C1=CC=C(Cl)C=C1 KLIWMKCTBFKERB-UHFFFAOYSA-N 0.000 claims description 3
- OKMSJBODIRWJPW-UHFFFAOYSA-N OC1=C(P(=O)(OC)OC)C=NN1C1=CC=C(F)C=C1 Chemical compound OC1=C(P(=O)(OC)OC)C=NN1C1=CC=C(F)C=C1 OKMSJBODIRWJPW-UHFFFAOYSA-N 0.000 claims description 3
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 3
- 230000021121 meiosis Effects 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 229910052700 potassium Inorganic materials 0.000 claims description 3
- 239000011591 potassium Substances 0.000 claims description 3
- NOBXAADYBYYJMJ-UHFFFAOYSA-N COP(=O)(OC)C1=C(O)N(C=2C=CC(Cl)=CC=2)N=C1C1=CC=CC=C1 Chemical compound COP(=O)(OC)C1=C(O)N(C=2C=CC(Cl)=CC=2)N=C1C1=CC=CC=C1 NOBXAADYBYYJMJ-UHFFFAOYSA-N 0.000 claims description 2
- HMZUSTVQZOEGMV-UHFFFAOYSA-N [2-(3,5-dimethylphenyl)-3-hydroxy-1,3-dihydropyrazol-4-yl]phosphonic acid Chemical compound CC1=CC(C)=CC(N2C(C(=CN2)P(O)(O)=O)O)=C1 HMZUSTVQZOEGMV-UHFFFAOYSA-N 0.000 claims description 2
- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- 239000008346 aqueous phase Substances 0.000 claims description 2
- 239000002585 base Substances 0.000 claims description 2
- 150000002429 hydrazines Chemical class 0.000 claims description 2
- 239000012535 impurity Substances 0.000 claims description 2
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims 3
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 2
- GHJDGTQYQPATGZ-UHFFFAOYSA-N 2-(4-chlorophenyl)-1-cyclohexyl-4-dimethoxyphosphorylpyrazol-3-one Chemical compound C=1C=C(Cl)C=CC=1N1C(=O)C(P(=O)(OC)OC)=CN1C1CCCCC1 GHJDGTQYQPATGZ-UHFFFAOYSA-N 0.000 claims 1
- HSUVDWYGGPMOBB-UHFFFAOYSA-N 2-(4-chlorophenyl)-4-dimethoxyphosphoryl-1-ethylpyrazol-3-one Chemical compound CCN1C=C(P(=O)(OC)OC)C(=O)N1C1=CC=C(Cl)C=C1 HSUVDWYGGPMOBB-UHFFFAOYSA-N 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 1
- 125000006502 nitrobenzyl group Chemical group 0.000 claims 1
- 208000037916 non-allergic rhinitis Diseases 0.000 claims 1
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- WESJNFANGQJVKA-UHFFFAOYSA-M sodium;2,3-dichloro-2-methylpropanoate Chemical compound [Na+].ClCC(Cl)(C)C([O-])=O WESJNFANGQJVKA-UHFFFAOYSA-M 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
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- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 239000004606 Fillers/Extenders Substances 0.000 description 3
- 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 3
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- 241000779819 Syncarpia glomulifera Species 0.000 description 1
- 244000269722 Thea sinensis Species 0.000 description 1
- 235000019714 Triticale Nutrition 0.000 description 1
- 235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 description 1
- GAHUJRSRQBLIMO-UHFFFAOYSA-N [2-(4-chlorophenyl)-3-hydroxy-1,3-dihydropyrazol-4-yl]phosphonic acid Chemical compound N1C=C(P(O)(O)=O)C(O)N1C1=CC=C(Cl)C=C1 GAHUJRSRQBLIMO-UHFFFAOYSA-N 0.000 description 1
- FJJCIZWZNKZHII-UHFFFAOYSA-N [4,6-bis(cyanoamino)-1,3,5-triazin-2-yl]cyanamide Chemical compound N#CNC1=NC(NC#N)=NC(NC#N)=N1 FJJCIZWZNKZHII-UHFFFAOYSA-N 0.000 description 1
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- 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
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- 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
- 230000001086 cytosolic effect Effects 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- SPCNPOWOBZQWJK-UHFFFAOYSA-N dimethoxy-(2-propan-2-ylsulfanylethylsulfanyl)-sulfanylidene-$l^{5}-phosphane Chemical compound COP(=S)(OC)SCCSC(C)C SPCNPOWOBZQWJK-UHFFFAOYSA-N 0.000 description 1
- 208000022602 disease susceptibility Diseases 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
- 238000009826 distribution Methods 0.000 description 1
- QYDYPVFESGNLHU-UHFFFAOYSA-N elaidic acid methyl ester Natural products CCCCCCCCC=CCCCCCCCC(=O)OC QYDYPVFESGNLHU-UHFFFAOYSA-N 0.000 description 1
- 238000005538 encapsulation Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 235000010944 ethyl methyl cellulose Nutrition 0.000 description 1
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- 230000008020 evaporation Effects 0.000 description 1
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- 235000013312 flour Nutrition 0.000 description 1
- 239000004459 forage Substances 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 235000004611 garlic Nutrition 0.000 description 1
- 230000002068 genetic effect Effects 0.000 description 1
- 238000010353 genetic engineering Methods 0.000 description 1
- 230000008303 genetic mechanism 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
- 150000002334 glycols Chemical class 0.000 description 1
- XDDAORKBJWWYJS-UHFFFAOYSA-N glyphosate Chemical compound OC(=O)CNCP(O)(O)=O XDDAORKBJWWYJS-UHFFFAOYSA-N 0.000 description 1
- 229940097068 glyphosate Drugs 0.000 description 1
- 239000001963 growth medium Substances 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 238000009396 hybridization Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 description 1
- 239000005414 inactive ingredient Substances 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 229910003480 inorganic solid Inorganic materials 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000012669 liquid formulation Substances 0.000 description 1
- XCOBTUNSZUJCDH-UHFFFAOYSA-B lithium magnesium sodium silicate Chemical compound [Li+].[Li+].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[Na+].[Na+].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].O1[Si](O2)([O-])O[Si]3([O-])O[Si]1([O-])O[Si]2([O-])O3.O1[Si](O2)([O-])O[Si]3([O-])O[Si]1([O-])O[Si]2([O-])O3.O1[Si](O2)([O-])O[Si]3([O-])O[Si]1([O-])O[Si]2([O-])O3.O1[Si](O2)([O-])O[Si]3([O-])O[Si]1([O-])O[Si]2([O-])O3.O1[Si](O2)([O-])O[Si]3([O-])O[Si]1([O-])O[Si]2([O-])O3.O1[Si](O2)([O-])O[Si]3([O-])O[Si]1([O-])O[Si]2([O-])O3 XCOBTUNSZUJCDH-UHFFFAOYSA-B 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
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- 230000008018 melting Effects 0.000 description 1
- 238000002844 melting Methods 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
- 229920003087 methylethyl cellulose Polymers 0.000 description 1
- 235000019713 millet Nutrition 0.000 description 1
- 238000003801 milling Methods 0.000 description 1
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- 150000002790 naphthalenes Chemical class 0.000 description 1
- 231100001184 nonphytotoxic Toxicity 0.000 description 1
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- UYDLBVPAAFVANX-UHFFFAOYSA-N octylphenoxy polyethoxyethanol Chemical compound CC(C)(C)CC(C)(C)C1=CC=C(OCCOCCOCCOCCO)C=C1 UYDLBVPAAFVANX-UHFFFAOYSA-N 0.000 description 1
- 238000009401 outcrossing Methods 0.000 description 1
- 229910052625 palygorskite Inorganic materials 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 239000003208 petroleum Chemical class 0.000 description 1
- 230000000885 phytotoxic effect Effects 0.000 description 1
- 239000001739 pinus spp. Substances 0.000 description 1
- 230000008121 plant development Effects 0.000 description 1
- 239000005648 plant growth regulator Substances 0.000 description 1
- 230000004983 pleiotropic effect Effects 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 150000003217 pyrazoles Chemical class 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- 150000004892 pyridazines Chemical class 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000017055 regulation of female receptivity Effects 0.000 description 1
- 238000009877 rendering Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000010153 self-pollination Effects 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- DHNUAKOQUGJUGA-UHFFFAOYSA-N silicon;sulfane Chemical compound [Si].S DHNUAKOQUGJUGA-UHFFFAOYSA-N 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
- 239000011343 solid material Substances 0.000 description 1
- 238000007711 solidification Methods 0.000 description 1
- 230000008023 solidification Effects 0.000 description 1
- 238000000935 solvent evaporation Methods 0.000 description 1
- 229940035044 sorbitan monolaurate Drugs 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000003892 spreading Methods 0.000 description 1
- 230000007480 spreading Effects 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 235000013616 tea Nutrition 0.000 description 1
- 230000002110 toxicologic effect Effects 0.000 description 1
- 231100000027 toxicology Toxicity 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
- 229940036248 turpentine Drugs 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 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
- 239000004563 wettable powder Substances 0.000 description 1
- 238000009736 wetting Methods 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
- 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
- A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
- A01N57/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds
- A01N57/24—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds containing heterocyclic radicals
-
- 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
- A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
- A01N57/26—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-nitrogen bonds
- A01N57/32—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-nitrogen bonds containing heterocyclic radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/645—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having two nitrogen atoms as the only ring hetero atoms
- C07F9/6503—Five-membered rings
- C07F9/65031—Five-membered rings having the nitrogen atoms in the positions 1 and 2
Landscapes
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Organic Chemistry (AREA)
- Agronomy & Crop Science (AREA)
- Plant Pathology (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Molecular Biology (AREA)
- Biochemistry (AREA)
- Breeding Of Plants And Reproduction By Means Of Culturing (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US11840899P | 1999-02-02 | 1999-02-02 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200106071B true ZA200106071B (en) | 2002-10-24 |
Family
ID=22378393
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200106071A ZA200106071B (en) | 1999-02-02 | 2001-07-24 | Production of phosphonopyrazoles. |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US6297194B1 (ja) |
| EP (1) | EP1149108A1 (ja) |
| JP (1) | JP2002536379A (ja) |
| CN (1) | CN1348457A (ja) |
| AU (1) | AU2865100A (ja) |
| CA (1) | CA2372002A1 (ja) |
| WO (1) | WO2000046229A1 (ja) |
| ZA (1) | ZA200106071B (ja) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9516824B2 (en) | 2012-02-14 | 2016-12-13 | The Board Of Trustees Of The Leland Stanford Junior University | Method for modulating the number of archesporial cells in a developing anther |
| RU2591858C1 (ru) * | 2015-06-24 | 2016-07-20 | Общество с ограниченной ответственностью "Научно-исследовательский институт природных газов и газовых технологий - Газпром ВНИИГАЗ" | Состав для сохранения устойчивости стенок скважины (варианты) |
| CA3031701A1 (en) * | 2016-07-25 | 2018-02-01 | Bejo Zaden B.V. | Hybrid true potato seed |
Family Cites Families (36)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE930212C (de) * | 1953-02-10 | 1955-07-11 | Bayer Ag | Verfahren zur Herstellung von neuen Phosphonsaeuredialkylestern |
| US3576814A (en) | 1970-01-30 | 1971-04-27 | Rohm & Haas | N-aryl pyrid-2-ones |
| US4028084A (en) | 1974-10-11 | 1977-06-07 | Rohm And Haas Company | Derivatives of 3-carboxy pyrid-2-ones |
| US4038065A (en) | 1974-10-11 | 1977-07-26 | Rohm And Haas Company | 1-alkylpyrid-2-one |
| US4115101A (en) | 1976-05-24 | 1978-09-19 | Rohm And Haas Company | 1-Aryl-4-pyridones |
| US4051142A (en) | 1976-05-24 | 1977-09-27 | Rohm And Haas Company | 1-Aryl-4-pyridones |
| PL115813B1 (en) | 1977-03-10 | 1981-05-30 | Plant growth regulator | |
| US4345934A (en) | 1977-03-10 | 1982-08-24 | Rohm And Haas Company | Method of producing hybrid cereal grain seeds by application of 1-aryl-1,4-dihydro-4-oxo(thio)-pyridazines |
| US4238220A (en) | 1977-07-15 | 1980-12-09 | Rohm And Haas Company | 1-Aryl-5-carboxy-2-pyridones and derivatives thereof |
| GB1603896A (en) | 1977-08-22 | 1981-12-02 | Rohm & Haas | Method for the agricultural production of ergot using chemical gametocides |
| 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 |
| US4936904A (en) | 1980-05-12 | 1990-06-26 | Carlson Glenn R | Aryl-4-oxonicotinates useful for inducing male sterility in cereal grain plants |
| US4707181A (en) | 1980-10-03 | 1987-11-17 | Rohm And Haas Company | 1-aryl-1,4-dihydro-4-oxo-3,5-dicarboxypyridazine derivatives and their use as plant growth regulators and hybridizing agents |
| GR75799B (ja) | 1980-10-03 | 1984-08-02 | Ici Plc | |
| US4732603A (en) | 1980-10-03 | 1988-03-22 | Rohm And Haas Company | 1-aryl-1,4-dihydro-4-oxo-5-carboxypyridazine derivatives and their use as plant growth regulators and hybridizing agents |
| US5062880A (en) | 1980-10-03 | 1991-11-05 | Monsanto Company | 1-aryl-1,4-dihydro-4-oxo-5-carboxypyridazine derivatives and their use as plant growth regulators and hybridizing agents |
| CA1156850A (en) | 1980-12-23 | 1983-11-15 | Anson R. Cooke | Male gametocide method of small grain plant |
| US4623378A (en) | 1983-08-10 | 1986-11-18 | Ciba-Geigy Corporation | Gametocidal pyridazinylcarboxylic acid derivatives |
| EP0138662A3 (en) | 1983-09-14 | 1985-08-14 | Lafarge Coppee | Pollen suppressant comprising a 3-carboxyalkoxyaminocarbonylpyridazine |
| US4729782A (en) | 1983-09-14 | 1988-03-08 | Lafarge Coppee | Pollen suppressant comprising a fused pyridazinone |
| US4604134A (en) | 1983-09-14 | 1986-08-05 | Lafarge Coppee | Pollen suppressant comprising a fused pyridazine |
| US4714491A (en) | 1983-10-07 | 1987-12-22 | Stauffer Chemical Company | Diphenyl ether herbicides |
| DE3402308A1 (de) | 1984-01-24 | 1985-08-01 | Bayer Ag, 5090 Leverkusen | Herbizide mittel auf basis von pyrazolderivaten |
| US4735649A (en) | 1985-09-25 | 1988-04-05 | Monsanto Company | Gametocides |
| KR870008849A (ko) | 1986-03-19 | 1987-10-21 | 메어리 앤 턱커 | 생식자 박멸효능을 갖는 피라졸류 |
| US4966623A (en) | 1986-03-19 | 1990-10-30 | Ackmann Stephen A | Use of gametocidal pyrazoles to produce hybrid seed |
| US4925477A (en) | 1986-08-29 | 1990-05-15 | Research Corporation | Chemical hybridizing agents |
| US4747871A (en) | 1987-01-07 | 1988-05-31 | Monsanto Company | 2,6-bis(trifluoromethyl)-3-hydroxycarbonyl pyridine, salts and gametocides |
| ES2004489A4 (es) | 1987-01-07 | 1989-01-16 | Monsanto Co | Gametocidas de piridina. |
| US5332716A (en) | 1988-09-13 | 1994-07-26 | Jeffrey Labovitz | Pollen suppressant comprising a 5-oxy- or amino-substituted cinnoline |
| US5129939A (en) | 1988-09-13 | 1992-07-14 | Orsan | Pollen suppressant comprising a 5-oxy- or amino-substituted cinnoline |
| GB8821449D0 (en) | 1988-09-13 | 1988-10-12 | Ici Plc | Pyridazinone manufacture |
| US5169429A (en) | 1988-10-14 | 1992-12-08 | Monsanto Company | Hybridization of sunflowers and safflowers |
| US4962199A (en) | 1989-04-06 | 1990-10-09 | Monsanto Company | Pyridazines by magnesium halide catalyzed cyclization |
| CH680795A5 (ja) * | 1990-12-07 | 1992-11-13 | Ciba Geigy Ag | |
| JPH0699252A (ja) | 1992-09-19 | 1994-04-12 | Sumitomo Metal Ind Ltd | ロ−ル式薄板連続鋳造における鋳造後鋳片の処理方法 |
-
2000
- 2000-01-28 CN CN00805871A patent/CN1348457A/zh active Pending
- 2000-01-28 AU AU28651/00A patent/AU2865100A/en not_active Abandoned
- 2000-01-28 CA CA002372002A patent/CA2372002A1/en not_active Abandoned
- 2000-01-28 JP JP2000597299A patent/JP2002536379A/ja not_active Withdrawn
- 2000-01-28 EP EP00907093A patent/EP1149108A1/en not_active Withdrawn
- 2000-01-28 WO PCT/US2000/002421 patent/WO2000046229A1/en not_active Application Discontinuation
- 2000-02-02 US US09/497,017 patent/US6297194B1/en not_active Expired - Fee Related
-
2001
- 2001-07-24 ZA ZA200106071A patent/ZA200106071B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| JP2002536379A (ja) | 2002-10-29 |
| CA2372002A1 (en) | 2000-08-10 |
| AU2865100A (en) | 2000-08-25 |
| US6297194B1 (en) | 2001-10-02 |
| EP1149108A1 (en) | 2001-10-31 |
| WO2000046229A1 (en) | 2000-08-10 |
| CN1348457A (zh) | 2002-05-08 |
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