CN87101796A - 1-苯基咪唑-羧酸酰胺的制造方法及其作为植物生长调节剂的应用 - Google Patents
1-苯基咪唑-羧酸酰胺的制造方法及其作为植物生长调节剂的应用 Download PDFInfo
- Publication number
- CN87101796A CN87101796A CN198787101796A CN87101796A CN87101796A CN 87101796 A CN87101796 A CN 87101796A CN 198787101796 A CN198787101796 A CN 198787101796A CN 87101796 A CN87101796 A CN 87101796A CN 87101796 A CN87101796 A CN 87101796A
- Authority
- CN
- China
- Prior art keywords
- plant
- compound
- formula
- growth regulator
- carboxylic acid
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 239000005648 plant growth regulator Substances 0.000 title claims abstract description 13
- 238000000034 method Methods 0.000 title claims description 15
- ZVKWLRUJGPDSMY-UHFFFAOYSA-N 1-phenylimidazole-2-carboxamide Chemical compound NC(=O)C1=NC=CN1C1=CC=CC=C1 ZVKWLRUJGPDSMY-UHFFFAOYSA-N 0.000 title abstract description 4
- 238000004519 manufacturing process Methods 0.000 title abstract description 4
- 150000001875 compounds Chemical class 0.000 claims abstract description 35
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 4
- 150000002367 halogens Chemical class 0.000 claims abstract description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 16
- 150000003839 salts Chemical class 0.000 claims description 12
- 229910021529 ammonia Inorganic materials 0.000 claims description 8
- 239000000460 chlorine Substances 0.000 claims description 7
- 230000008635 plant growth Effects 0.000 claims description 7
- 238000002360 preparation method Methods 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 239000000463 material Substances 0.000 claims description 5
- 150000002431 hydrogen Chemical class 0.000 claims description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 150000002460 imidazoles Chemical class 0.000 claims description 2
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims 1
- 239000000126 substance Substances 0.000 abstract description 20
- -1 R 2=H Chemical group 0.000 abstract description 19
- 230000000694 effects Effects 0.000 abstract description 5
- 240000007594 Oryza sativa Species 0.000 abstract description 3
- 235000007164 Oryza sativa Nutrition 0.000 abstract description 3
- 150000002148 esters Chemical class 0.000 abstract description 3
- 235000009566 rice Nutrition 0.000 abstract description 3
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 abstract description 2
- 239000013543 active substance Substances 0.000 description 21
- 241000196324 Embryophyta Species 0.000 description 10
- 239000000203 mixture Substances 0.000 description 10
- 239000003795 chemical substances by application Substances 0.000 description 8
- 230000012010 growth Effects 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 239000002131 composite material Substances 0.000 description 5
- 239000004495 emulsifiable concentrate Substances 0.000 description 5
- 239000003995 emulsifying agent Substances 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 239000004563 wettable powder Substances 0.000 description 5
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 229920000151 polyglycol Polymers 0.000 description 4
- 239000010695 polyglycol Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 239000007921 spray Substances 0.000 description 4
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- 150000003863 ammonium salts Chemical class 0.000 description 3
- 238000010790 dilution Methods 0.000 description 3
- 239000012895 dilution Substances 0.000 description 3
- 239000006185 dispersion Substances 0.000 description 3
- 150000002191 fatty alcohols Chemical class 0.000 description 3
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000011236 particulate material Substances 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 239000000454 talc Substances 0.000 description 3
- 229910052623 talc Inorganic materials 0.000 description 3
- 235000012222 talc Nutrition 0.000 description 3
- 239000000080 wetting agent Substances 0.000 description 3
- UDPGUMQDCGORJQ-UHFFFAOYSA-N (2-chloroethyl)phosphonic acid Chemical compound OP(O)(=O)CCCl UDPGUMQDCGORJQ-UHFFFAOYSA-N 0.000 description 2
- JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical compound OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 description 2
- 239000005995 Aluminium silicate Substances 0.000 description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical group C1CO1 IAYPIBMASNFSPL-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
- 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
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 125000003342 alkenyl group Chemical group 0.000 description 2
- 235000012211 aluminium silicate Nutrition 0.000 description 2
- 235000011114 ammonium hydroxide Nutrition 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 239000000428 dust Substances 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 230000002349 favourable effect Effects 0.000 description 2
- 239000003337 fertilizer Substances 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 238000000227 grinding Methods 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 239000002480 mineral oil Substances 0.000 description 2
- 235000010446 mineral oil Nutrition 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 230000001105 regulatory effect Effects 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- XFRVVPUIAFSTFO-UHFFFAOYSA-N 1-Tridecanol Chemical compound CCCCCCCCCCCCCO XFRVVPUIAFSTFO-UHFFFAOYSA-N 0.000 description 1
- SVOAUHHKPGKPQK-UHFFFAOYSA-N 2-chloro-9-hydroxyfluorene-9-carboxylic acid Chemical compound C1=C(Cl)C=C2C(C(=O)O)(O)C3=CC=CC=C3C2=C1 SVOAUHHKPGKPQK-UHFFFAOYSA-N 0.000 description 1
- ANHAEBWRQNIPEV-UHFFFAOYSA-N 2-chloroethyl dihydrogen phosphate Chemical compound OP(O)(=O)OCCCl ANHAEBWRQNIPEV-UHFFFAOYSA-N 0.000 description 1
- MSBVBOUOMVTWKE-UHFFFAOYSA-N 2-naphthalen-2-ylnaphthalene Chemical group C1=CC=CC2=CC(C3=CC4=CC=CC=C4C=C3)=CC=C21 MSBVBOUOMVTWKE-UHFFFAOYSA-N 0.000 description 1
- NIOYEINNWHTIIM-UHFFFAOYSA-N 3-(2,6-diethylphenyl)imidazole-4-carboxylic acid Chemical compound CCC1=CC=CC(CC)=C1N1C(C(O)=O)=CN=C1 NIOYEINNWHTIIM-UHFFFAOYSA-N 0.000 description 1
- FOGYNLXERPKEGN-UHFFFAOYSA-N 3-(2-hydroxy-3-methoxyphenyl)-2-[2-methoxy-4-(3-sulfopropyl)phenoxy]propane-1-sulfonic acid Chemical compound COC1=CC=CC(CC(CS(O)(=O)=O)OC=2C(=CC(CCCS(O)(=O)=O)=CC=2)OC)=C1O FOGYNLXERPKEGN-UHFFFAOYSA-N 0.000 description 1
- FSVMTMFHLLEQAS-UHFFFAOYSA-N 3-phenylimidazole-4-carboxylic acid Chemical class OC(=O)C1=CN=CN1C1=CC=CC=C1 FSVMTMFHLLEQAS-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- 244000025254 Cannabis sativa Species 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
- QSJXEFYPDANLFS-UHFFFAOYSA-N Diacetyl Chemical group CC(=O)C(C)=O QSJXEFYPDANLFS-UHFFFAOYSA-N 0.000 description 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical group O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005976 Ethephon Substances 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 240000005979 Hordeum vulgare Species 0.000 description 1
- 235000007340 Hordeum vulgare Nutrition 0.000 description 1
- 244000211187 Lepidium sativum Species 0.000 description 1
- 235000007849 Lepidium sativum Nutrition 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical class CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 description 1
- IFVRMHVMSSPQLZ-UHFFFAOYSA-N P(O)(O)=O.ClCC Chemical compound P(O)(O)=O.ClCC IFVRMHVMSSPQLZ-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 229910004298 SiO 2 Inorganic materials 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 239000005864 Sulphur Substances 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 230000000274 adsorptive effect Effects 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000002877 alkyl aryl group Chemical group 0.000 description 1
- 150000004996 alkyl benzenes Chemical class 0.000 description 1
- 150000008052 alkyl sulfonates Chemical class 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- HUTDUHSNJYTCAR-UHFFFAOYSA-N ancymidol Chemical compound C1=CC(OC)=CC=C1C(O)(C=1C=NC=NC=1)C1CC1 HUTDUHSNJYTCAR-UHFFFAOYSA-N 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 239000012752 auxiliary agent Substances 0.000 description 1
- 239000000440 bentonite Substances 0.000 description 1
- 229910000278 bentonite Inorganic materials 0.000 description 1
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
- 229940077388 benzenesulfonate Drugs 0.000 description 1
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 1
- 239000012964 benzotriazole Substances 0.000 description 1
- 229960004217 benzyl alcohol Drugs 0.000 description 1
- 235000019445 benzyl alcohol Nutrition 0.000 description 1
- HCWYXKWQOMTBKY-UHFFFAOYSA-N calcium;dodecyl benzenesulfonate Chemical compound [Ca].CCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 HCWYXKWQOMTBKY-UHFFFAOYSA-N 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- UHZZMRAGKVHANO-UHFFFAOYSA-M chlormequat chloride Chemical compound [Cl-].C[N+](C)(C)CCCl UHZZMRAGKVHANO-UHFFFAOYSA-M 0.000 description 1
- OEYIOHPDSNJKLS-UHFFFAOYSA-N choline Chemical compound C[N+](C)(C)CCO OEYIOHPDSNJKLS-UHFFFAOYSA-N 0.000 description 1
- 229960001231 choline Drugs 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- PSLIMVZEAPALCD-UHFFFAOYSA-N ethanol;ethoxyethane Chemical compound CCO.CCOCC PSLIMVZEAPALCD-UHFFFAOYSA-N 0.000 description 1
- 238000007046 ethoxylation reaction Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 230000000855 fungicidal effect Effects 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 150000004676 glycans Chemical class 0.000 description 1
- 239000000122 growth hormone Substances 0.000 description 1
- 239000003966 growth inhibitor Substances 0.000 description 1
- 239000003630 growth substance Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Substances CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 1
- 239000005556 hormone Substances 0.000 description 1
- 229940088597 hormone Drugs 0.000 description 1
- 229940042795 hydrazides for tuberculosis treatment Drugs 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 229910052622 kaolinite Inorganic materials 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- 150000001457 metallic cations Chemical class 0.000 description 1
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-M methanesulfonate group Chemical class CS(=O)(=O)[O-] AFVFQIVMOAPDHO-UHFFFAOYSA-M 0.000 description 1
- 150000002790 naphthalenes Chemical class 0.000 description 1
- 229920002113 octoxynol Polymers 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 239000012466 permeate Substances 0.000 description 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
- 239000003375 plant hormone Substances 0.000 description 1
- 229920001495 poly(sodium acrylate) polymer Polymers 0.000 description 1
- 229920001522 polyglycol ester Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229920001282 polysaccharide Polymers 0.000 description 1
- 239000005017 polysaccharide Substances 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 229910052903 pyrophyllite Inorganic materials 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 210000000582 semen Anatomy 0.000 description 1
- 229920005552 sodium lignosulfonate Polymers 0.000 description 1
- NNMHYFLPFNGQFZ-UHFFFAOYSA-M sodium polyacrylate Chemical compound [Na+].[O-]C(=O)C=C NNMHYFLPFNGQFZ-UHFFFAOYSA-M 0.000 description 1
- KZOJQMWTKJDSQJ-UHFFFAOYSA-M sodium;2,3-dibutylnaphthalene-1-sulfonate Chemical compound [Na+].C1=CC=C2C(S([O-])(=O)=O)=C(CCCC)C(CCCC)=CC2=C1 KZOJQMWTKJDSQJ-UHFFFAOYSA-M 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 235000020354 squash Nutrition 0.000 description 1
- 229960002673 sulfacetamide Drugs 0.000 description 1
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 238000001149 thermolysis Methods 0.000 description 1
- XPDWGBQVDMORPB-UHFFFAOYSA-N trifluoromethane acid Natural products FC(F)F XPDWGBQVDMORPB-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 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
- A01N43/50—1,3-Diazoles; Hydrogenated 1,3-diazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two 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
- C07D233/90—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Environmental Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Plant Pathology (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
用作植物生长调节剂的1-苯基咪唑羧酸酰胺及其制造法。
化学式(I)表示的一些化合物及其盐类作为植物生长调节剂(尤其对水稻作物)具有非常好的效果。
式中R1＝(C1—C3)烷基，R2＝H、甲基或卤素。
Description
从DE-A3，217，094已知1-苯基咪唑-5-羧酸衍生物可用作杀霉菌剂、除草剂和植物生长调节剂。
这些化合物具有化学通式（A）
式中R1为氢、苯基、烷基、链烯基、金属阳离子或铵、其中烷基、链烯基可被卤素、烷氧基或二烷基氨基取代。R2为被取代过的苯基，X＝氧、硫或氮，在X＝氮的情况下，两个R1基连在X上。
意外地发现，挑选出在DE-A3，217，094中未叙述过的1-苯基咪唑羧酸酰胺（特别是对水稻）具有特别强的调节植物生长的作用。因此本发明的任务涉及化学式Ⅰ的一些化合物。
其中R1为彼此独立的（C1-C3）烷基。R2为氢、甲基或卤素以及它们的可用于农业中的盐。
R1尤其表示乙基，R2尤其表示氢
此外，本发明的任务还涉及化学式Ⅰ的化合物的制造方法。其特征是将具有化学式Ⅱ的化合物进行氨解。
式中R1，R2具有上述意义，R3＝-O-R4、-OH、Cl、
化学式所表示的基。R4＝（C1-C3）烷基。如有需要，可把得到的化合物转化成其盐。
氨解可按一般常用的方法进行，例如：
-用含有R3＝OR4的一些化合物与氨或加热时能释放出氨的物质（如尿素、甲酰胺或碳酸铵），必要时加压，在温度为100和250℃之间进行反应（实例见Houben-Weyl Ⅷ第656页）;或
-将化学式Ⅱ表示的含有R3＝OH的一些化合物转化成一种铵盐，然后使此铵盐进行热分解。铵盐可通过酸与氨或与上述释出氨的物质反应制取（实例见Houben-Weyl Ⅷ第645页）;或
-用化学式Ⅱ表示的含有R3＝Cl、
的化合物与氨水或气态氨于惰性溶剂中，在0至100℃进行反应（实例见Organikum 1973，第453页）。
可用于农业中的化学式Ⅰ表示的一些盐是咪唑盐（Imidazo-liumsalze）;这类盐可按已知的方法用强酸例如盐酸、硫酸、甲磺酸、氯代乙基膦酸或三氯醋酸在pH值≤α的条件来制备。
用本发明的化合物具有典型的调节植物生长的效果，这种化合物可低剂量使用。它们对植物本身的新陈代谢起到了调节作用。可用来有目的地对植物机体（Pflanzeninhaltsstoffen）产生影响，
用来提高产量，促使庄稼早熟（Ernteerleichterung）和使植物茁壮生长（Wuchsstauchung）。其次，这些化合物也适合用来普遍控制和阻止植物不符合人们愿望的生长，但是不杀死植物。对许多单子叶和双子叶作物起着抑制植物生长的重要作用，由此可以减少倒伏或完全阻止倒伏。这些化合物所具有的植物生长调节剂的作用，用作水稻生长抑制剂是特别突出的。本发明的任务也包括调节植物生长的药剂，此药剂的特点是至少含有本发明的化合物之一的有效成份。
本发明的化合物，需要时，可和其它有效成份混合，以通常的方法制成可湿粉剂、可乳化浓缩物、可喷洒的溶液、粉雾剂、分散液、颗粒料或微型颗粒料后使用。
可湿粉剂是可在水中均匀分散的制剂，此制剂除含有效物质外，还含有稀释剂或惰性物质或湿润剂，如：聚乙氧基脂肪醇、烷基磺酸盐或烷基苯基磺酸盐和/或分散助剂，如：木质素磺酸钠、2，2′-二萘基甲烷-6，6′二磺酸钠、二丁基萘磺酸钠或者还有油酰甲基中磺酸钠。可湿粉剂是按通常方法制备的，例如将各组份研磨并混合之。
可乳化的浓缩物可以通过例如将有效物质溶于某种惰性有机溶剂如：丁醇、环己酮、二甲基甲酰胺、二甲苯或沸点较高的芳香化合物、或脂肪族碳氢化合物，或脂环碳氢化合物中，添加一种或几种乳化剂而制成。有效物质为液体时，也可完全不用溶剂或用一部份溶剂。作为乳化剂的例如有：烷基-芳基磺酸钙盐，如十二烷基苯磺酸钙或非离子型的乳化剂，如：脂肪酸聚乙二醇酯、烷基芳基聚乙二醇醚、脂肪醇聚乙二醇醚、环氧丙烷-环氧乙烷-缩合物、脂肪醇-环氧丙烷-缩合物、烷基聚乙二醇醚、脱水山梨醇脂肪酸酯、聚氧乙烯脱水山梨醇酸酯或聚氧乙烯山梨糖醇酯。
粉雾剂可以将有效物质和细粉状的固体物质在一起研磨而获得。这些细粉状固体物例如有滑石、天然粘土、如高岭土、皂土、叶蜡石或硅藻土。颗粒料既可将有效物质喷洒到粒状的有吸附能力的惰性物质上而产生，也可借助于粘合剂，例如借助于聚乙烯醇、聚丙烯酸钠或矿物油，将浓缩的有效物质涂到载体物质的表面，例如涂到砂子、高岭石表面或粒状的惰性物质表面而制成。也可将合适的有效物质按照生产肥料颗粒常用的方法-如果需要的话，与肥料混合-制成颗粒。
在可湿粉剂中有效物质的浓度约为5～90重量%，其余的重量%由普通的配方成份组成。在可乳化的浓缩物中，有效物质可含3～80%重量%。粉雾状的配方至少含有0.025～20重量%的有效物质，可喷洒的溶液含约2～20%重量%的有效物质。在颗粒料中，有效物质的含量，部份取决于有效化合物是液体或固体，以及用的是哪些成粒助剂，哪些填充剂等等。此外，上述有效物质的一些配方，可能还加有通用的粘接剂、润湿剂、分散剂、乳化剂、渗透剂、溶剂、填料或载体。
需要时将市售的浓缩物按通常的方法稀释使用，例如假如是粉剂、可乳化的浓缩物、分散剂和微粒料（某些情况下）可用水稀释。粉雾状的和颗粒状的制品以及可喷洒的溶液通常不再用其它惰性物质稀释。
本发明的化合物的用量，一般情况下每公顷用0.02至2.5公斤有效物质，最好是每公顷0.05至1-5公斤。
在实际使用时将本发明的化合物，特别是将例子中提及的化合物，在可能的情况下和已知植物生长调节剂复配使用也是有利的。这样一些已知的植物生长调节剂是化学式：
R-CH2-CH2-N+（CH3）3Cl表示的一些化合物。式中R＝OH或Cl（R＝Cl时普通各称为矮壮素。此外是氯化N，N-二甲基哌啶盐（助壮素），α-环丙基-4-甲氧基-α（嘧啶-戊基）苯甲醇（嘧啶醇），（3aα，4β，4aα，6aα，7β，7aα）-1-（4-氯苯基）-3a，4，4a，6a，7，7a-六氢化-4，7-甲撑-1H-〔1，2〕二乙酰基〔3，4-f〕苯并三唑（Tetcylacis），琥珀酸-单-2，2-二甲基酰肼（二氨基二嗪农），6-羟基-2H-膦二氮（杂）苯-3-酮（马来酸酐），2-氯-9-羟基-9H-芴-9-羧酸（Chlor-flurenol），5′-（三氟甲磺酰胺基）-2′，4′-二甲基乙酰磺胺（Mefluidid），2-氯乙基膦酸（乙烯剂）。
这些化合物的植物生长调节的作用，在植物生长调节剂工作小组所写的植物生长调节剂手册1981年第二版（Plant Growth Regulator Handbook of the Plant Growth Regulator Working Group 2d.Ed.1981）中已有叙述。
原则上也可用与之相应的一些盐类代替矮壮素或助壮素，这些盐不含氯化物离子，而含有其它常用阴离子、如溴化物、硝酸盐或硫酸盐。
将化学式Ⅰ表示的一些化合物，特别是实例Ⅰ的化合物或其盐与Ethephon复配用干温带作物，譬如用于十字花科植物（例如油菜籽）或禾本科植物（例如大麦）也是有利的。
这些复配既可作成各组份的混合配方，然后按普通方法用水稀释后使用，或可通过用水将各单独的复配组份稀释作成所谓罐混合物，也有可依次将各组份投入使用，这就是说将这些组份按单独的配方施用。
也可将化学通式（Ⅰ）表示的一些化合物和天然激素或植物激素如植物生长激素或细胞分裂素复配。
配方实例：
例1
用下面的方法可获得粉雾剂：
a）将10份重量的有效物质和90份重量的滑石或其它惰性物质混合，放在锤磨机中加以粉碎。或b）将60份重量的有效物质，35份重量的滑石和5份重量的粘合剂（例如多糖，如Rh
ne-Poulenc股份公司用的Rhodopol）用同样方法均化。
例2
用下面的方法可获得一种在水中容易分散的可湿粉剂：25份重量的有效物质，64份重量的含高岭土的石英作为惰性物质，10份重量的木质素磺酸钾和1份重量油酰甲基牛磺酸钠作为润湿剂和分散助剂混合在一起，放在一个园锥磨中磨细。一种含有5%的有效物质的配合料可按如下的组成和配比配制;5%的有效物质，6%的磺化萘/甲醛缩合物（例如Hoechst公司的Dispersogen A
），2%的烷基萘磺酸钠盐（例如Hoechst公司的Leonil DB
），5%的由聚丙二醇和SiO2（例如Hoechst公司的Acrotin 341
）组成的混合物，25%的硅酸盐（例如Degussa公司的Sipernat
）和57%的1777型高岭土。
例3
用下面的方法可以获得一种在水中容易分散的分散浓缩物：将20份重量的有效物质和6份重量的烷基酚聚乙醇醚（例如Rohm and Haas公司的Triton X 207
），3份重量的异十三醇聚乙二醇醚（8个环氧乙烷单元）及71份重量的石蜡基矿物油（沸点范围约为255至377℃以上。）混合，在球磨机中研磨至细度为5μm以下。
例4
将15份重量的有效物质，75份重量的用作溶剂的环己酮和10份重量的用作乳化剂的乙氧基化壬酚（10个环氧乙烷单元）混合在一起得到可乳化浓缩物。
化学实例
例1
1-（2，6-二乙基苯基）-咪唑-5-羧酸酰胺：将24.4克（0.1摩尔）1-（2，6-二乙基苯基）-咪唑-5-羧酸，一部份一部份地加到36克（0.3摩尔）亚硫酰（二）氯和1毫升二甲基甲酰胺的混合物中，加完之后，加热到80℃，直到不再产生气体，让其冷却，所得的固体沉淀放在真空中烘干，并将干燥之固体物在不停地搅拌下一部分一部分地加入到150毫升用冰冷却的浓氨水溶液中。在室温下搅拌一小时过滤沉淀物并烘干之，得到20.2克1-（2，6-二乙基苯基）-咪唑-5-羧酸酰胺无色固体物，其熔点为171-171.5℃（醋酸乙酯-己烷）;收率为理论值的83%。
其它例子列于表1中
表1 咪唑-5-羧酸酰胺
例号 R Fp℃（熔点）
2 2，6-二甲基-苯基
3 2-乙基-6-甲基-苯基 150-154
4 2-乙基-6-异丙基-苯基 198-203
5 2-异丙基-6-甲基-苯基
6 2，6-二异丙基-苯基
7 2，6-二乙基-苯基（氯化氢） 树脂
8 〃 （氯乙烷膦酸酯） 树脂
9 2，6-二乙基-3-甲基-苯基 147-151
10 2，6-二乙基-4-甲基-苯基
11 2，6-二乙基-4-溴-苯基
12 2，6-二乙基-3-氯-苯基 188-193
13 2，6-二乙基-苯基（硫酸氢盐） 178（分解）
14 2，6-二乙基-苯基（甲磺酸酯） 182-186
15 2，6-二乙基-苯基（三氯乙酸酯） 80（分解）
生物实例
抑制水稻生长
种植水稻植物并在其分蘖最旺盛的阶段用本发明的化合物及DE-A3217094的对比化合物加以处理，这些化合物既可以喷洒使用，也可以直接加在水中。
处理三星期后，测定所有植物的额外生长。并以对照植物额外生长的百分数计算抑制生长率。还须注意化合物的植物毒性。抑制生长率以百分值表示：100%代表生长停止，0%代表相当于未处理的对照的生长植物。
表2
按上述例子编号 使用浓度 抑制生长率 植物毒性
化合物 （公斤/公顷） %
1 1.25 35 无损害
0.62 29 〃
3 1.25 12 有损害
0.62 7 〃
44 1.25 16 无损害
0.62 11 〃
7 1.25 32 无损害
0.62 27 〃
8 1.25 31 无损害
0.62 25 〃
13 1.25 29 无损害
0.62 24 〃
14 1.25 26 无损害
0.62 21 〃
15 1.25 27 无损害
0.62 20 〃
A 1.25 11 无损害
0.62 7 〃
Claims (5)
1、制备农用的式(Ⅰ)
(式中R1分别代表(C1-C3)烷基，
R2代表氢、甲基或卤素)化合物或其盐的方法，其特征是将式(Ⅱ)
(式中R3代表-O-R4，-OH，氯，
或
，
R4代表(C1-C8)烷基)化合物进行氨解，需要时，可将所得的化合物转变成它们的咪唑盐。
2、按权利要求1的制备方法，其中式（Ⅰ）的R2为氢。
3、含有有效量的权利要求1或2中所述的通式（Ⅰ）化合物或其盐的植物生长调节剂。
4、使用权利要求1或2中所述的通式（Ⅰ）化合物或其盐作为植物生长调节剂。
5、调节植物生长的方法，此方法包括施用有效量的权利要求1或2所述的通式（Ⅰ）化合物或其盐于植物体或种植面积上。
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEP3608143.4 | 1986-03-12 | ||
| DE19863608143 DE3608143A1 (de) | 1986-03-12 | 1986-03-12 | 1-phenylimidazolcarbonsaeureamide, ihre herstellung sowie ihre verwendung als wachstumsregulatoren |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN87101796A true CN87101796A (zh) | 1987-09-23 |
Family
ID=6296109
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN198787101796A Pending CN87101796A (zh) | 1986-03-12 | 1987-03-10 | 1-苯基咪唑-羧酸酰胺的制造方法及其作为植物生长调节剂的应用 |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US4755213A (zh) |
| EP (1) | EP0243615B1 (zh) |
| JP (1) | JPS62212374A (zh) |
| CN (1) | CN87101796A (zh) |
| AT (1) | ATE61800T1 (zh) |
| AU (1) | AU596829B2 (zh) |
| DD (1) | DD259342A5 (zh) |
| DE (2) | DE3608143A1 (zh) |
| DK (1) | DK124987A (zh) |
| ES (1) | ES2021621B3 (zh) |
| GR (1) | GR3001708T3 (zh) |
| HU (1) | HUT43241A (zh) |
| IL (1) | IL81840A0 (zh) |
| PH (1) | PH22674A (zh) |
| PT (1) | PT84467B (zh) |
| ZA (1) | ZA871757B (zh) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102321027A (zh) * | 2011-10-09 | 2012-01-18 | 中国药科大学 | 一种咪唑-4-甲酸酰胺类衍生物的制备方法 |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3627155A1 (de) * | 1986-08-11 | 1988-02-18 | Schering Ag | Imidazol-derivate |
| DE3902439A1 (de) * | 1989-01-27 | 1990-08-02 | Basf Ag | Pflanzenschuetzende mittel auf basis von 1-aryl- bzw. 1-hetarylimidazolcarbonsaeureestern |
| US5211737A (en) * | 1989-01-31 | 1993-05-18 | Basf Aktiengesellschaft | 4-arryl-2-haloimidazole-5-carboxylic esters, the preparation and use thereof |
| CA2015366C (en) * | 1989-05-05 | 2001-09-11 | Rhone-Poulenc Agrochimie | Pesticidal 1-arylimidazoles |
| US5223525A (en) * | 1989-05-05 | 1993-06-29 | Rhone-Poulenc Ag Company | Pesticidal 1-arylimidazoles |
| CA2032289A1 (en) * | 1989-12-29 | 1991-06-30 | Joseph A. Finkelstein | Substituted 5-(alkyl) carboxamide imidazoles |
| WO2012087980A1 (en) | 2010-12-21 | 2012-06-28 | Agraquest, Inc. | Sandpaper mutants of bacillus and methods of their use to enhance plant growth, promote plant health and control diseases and pests |
| MX2014002890A (es) | 2011-09-12 | 2015-01-19 | Bayer Cropscience Lp | Metodo para mejorar la salud y/o promover el crecimiento de una planta y/o mejorar la maduracion de frutos. |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3217094A1 (de) * | 1982-05-07 | 1983-11-10 | Hoechst Ag, 6230 Frankfurt | 1-substituierte imidazol-5-carbonsaeurederivate, ihre herstellung sowie ihre verwendung als biozide |
| ATE41848T1 (de) * | 1984-06-05 | 1989-04-15 | Hoechst Ag | Pflanzenwachstumsregulierende mittel. |
| DE3444918A1 (de) * | 1984-12-08 | 1986-06-12 | Hoechst Ag, 6230 Frankfurt | 1-phenyl-imidazol-5-carbonsaeure-derivate, ein verfahren zu ihrer herstellung und ihre verwendung als wachstumsregulatoren |
| DE3514116A1 (de) * | 1985-04-19 | 1986-10-23 | Hoechst Ag, 6230 Frankfurt | Neue cyclohexyl- und cyclohexenylimidazolverbindungen, verfahren zu ihrer herstellung und ihre verwendung als pflanzenwachstumsregulatoren |
-
1986
- 1986-03-12 DE DE19863608143 patent/DE3608143A1/de not_active Withdrawn
-
1987
- 1987-03-03 DE DE8787103004T patent/DE3768697D1/de not_active Expired - Fee Related
- 1987-03-03 EP EP87103004A patent/EP0243615B1/de not_active Expired - Lifetime
- 1987-03-03 ES ES87103004T patent/ES2021621B3/es not_active Expired - Lifetime
- 1987-03-03 AT AT87103004T patent/ATE61800T1/de not_active IP Right Cessation
- 1987-03-10 IL IL81840A patent/IL81840A0/xx unknown
- 1987-03-10 JP JP62053202A patent/JPS62212374A/ja active Pending
- 1987-03-10 DD DD87300633A patent/DD259342A5/de unknown
- 1987-03-10 US US07/024,357 patent/US4755213A/en not_active Expired - Fee Related
- 1987-03-10 CN CN198787101796A patent/CN87101796A/zh active Pending
- 1987-03-11 HU HU871065A patent/HUT43241A/hu unknown
- 1987-03-11 AU AU69894/87A patent/AU596829B2/en not_active Ceased
- 1987-03-11 ZA ZA871757A patent/ZA871757B/xx unknown
- 1987-03-11 DK DK124987A patent/DK124987A/da not_active Application Discontinuation
- 1987-03-11 PH PH35013A patent/PH22674A/en unknown
- 1987-03-12 PT PT84467A patent/PT84467B/pt unknown
-
1991
- 1991-04-02 GR GR91400421T patent/GR3001708T3/el unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102321027A (zh) * | 2011-10-09 | 2012-01-18 | 中国药科大学 | 一种咪唑-4-甲酸酰胺类衍生物的制备方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| ATE61800T1 (de) | 1991-04-15 |
| DD259342A5 (de) | 1988-08-24 |
| PT84467A (en) | 1987-04-01 |
| JPS62212374A (ja) | 1987-09-18 |
| EP0243615A2 (de) | 1987-11-04 |
| PH22674A (en) | 1988-11-14 |
| US4755213A (en) | 1988-07-05 |
| PT84467B (en) | 1989-03-31 |
| ES2021621B3 (es) | 1991-11-16 |
| DE3608143A1 (de) | 1987-09-17 |
| DE3768697D1 (de) | 1991-04-25 |
| EP0243615A3 (en) | 1988-02-24 |
| GR3001708T3 (en) | 1992-11-23 |
| HUT43241A (en) | 1987-10-28 |
| EP0243615B1 (de) | 1991-03-20 |
| AU596829B2 (en) | 1990-05-17 |
| DK124987A (da) | 1987-09-13 |
| DK124987D0 (da) | 1987-03-11 |
| AU6989487A (en) | 1987-09-17 |
| IL81840A0 (en) | 1987-10-20 |
| ZA871757B (en) | 1987-09-01 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| AU2007343066B2 (en) | Novel agricultural composition | |
| ES2805999T3 (es) | Preparaciones con efecto inhibidor de ureasa mejorado y fertilizantes que contienen urea que las contienen | |
| EP0378985A1 (en) | Improved glyphosate formulations | |
| CN105149107B (zh) | 磷酸酯类化合物在含钙矿物浮选中的应用 | |
| CN1535939A (zh) | 一种肥料包膜组合物及其制造方法与多元包膜复合肥料 | |
| CN1034935C (zh) | 1-(3，4-二取代苯基)四唑啉酮衍生物，其制备方法及其除草剂用途 | |
| HUE031192T2 (hu) | Készítmény és eljárás növények termesztésének intenzifikálására és a növény termékenység növelésére | |
| CN87101796A (zh) | 1-苯基咪唑-羧酸酰胺的制造方法及其作为植物生长调节剂的应用 | |
| WO2021120232A1 (zh) | 一种植物生长调节剂及其制备方法和应用 | |
| CN85101424A (zh) | 咪唑啉酮的制备方法及其在植物防护方面的应用 | |
| CN85104656A (zh) | 土壤的处理方法和用于在土壤中保持氮的配方 | |
| CN85104629A (zh) | 植物生长调节剂的制备方法 | |
| CN1137506A (zh) | 水田中半翅目害虫的防治方法 | |
| CN87104125A (zh) | 3-苯甲酰基-4-氧代内酰胺 | |
| CN1163142C (zh) | 控制释放活性物质的植物保护粒剂 | |
| CN1122698C (zh) | 水稻育苗多功能床土调制剂及其制备工艺 | |
| KR20070060046A (ko) | 화학적 안정적, 건조 유동식, 저밀도, 먼지 없는, 구형의가용성 포스포로아미도티오에이트 과립 제조용 교반식볼링에 의한 건조 과립 제조 방법 | |
| JP4033986B2 (ja) | 粒状の有機物腐熟促進・土壌改良資材 | |
| JP2011246287A (ja) | 粒状肥料の製造方法 | |
| CN1216531C (zh) | 一种除草剂组合物 | |
| CN1166594C (zh) | 一种生化长效肥 | |
| US3728386A (en) | N-cycloalkylalkyl and n-cycloalkyl substituted phenyl ureas and halo acetamides | |
| KR20150014153A (ko) | 액상유황 함유 작물 보호제 제조방법 | |
| CN109748703A (zh) | 一种复合肥造粒剂及其制备方法 | |
| CN87103572A (zh) | 从烟酸衍生物为基的杀真菌剂及其制备 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C01 | Deemed withdrawal of patent application (patent law 1993) | ||
| WD01 | Invention patent application deemed withdrawn after publication |