IE74147B1 - Azole derivatives useful in controlling plant diseases and regulating plant growth - Google Patents
Azole derivatives useful in controlling plant diseases and regulating plant growthInfo
- Publication number
- IE74147B1 IE74147B1 IE37588A IE37588A IE74147B1 IE 74147 B1 IE74147 B1 IE 74147B1 IE 37588 A IE37588 A IE 37588A IE 37588 A IE37588 A IE 37588A IE 74147 B1 IE74147 B1 IE 74147B1
- Authority
- IE
- Ireland
- Prior art keywords
- formula
- derivative
- alkyl
- acid
- represented
- Prior art date
Links
- 150000007980 azole derivatives Chemical class 0.000 title claims abstract description 74
- 230000001105 regulatory effect Effects 0.000 title claims description 22
- 230000001276 controlling effect Effects 0.000 title claims description 21
- 230000008635 plant growth Effects 0.000 title claims description 21
- 201000010099 disease Diseases 0.000 title description 70
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 title description 70
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 60
- 238000000034 method Methods 0.000 claims abstract description 60
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 29
- 125000005843 halogen group Chemical group 0.000 claims abstract description 24
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 21
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 21
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract 2
- 239000001257 hydrogen Substances 0.000 claims abstract 2
- 150000001875 compounds Chemical class 0.000 claims description 127
- 239000000203 mixture Substances 0.000 claims description 103
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 60
- -1 benzyl halide Chemical class 0.000 claims description 43
- 230000008569 process Effects 0.000 claims description 34
- BGTOWKSIORTVQH-HOSYLAQJSA-N cyclopentanone Chemical class O=[13C]1CCCC1 BGTOWKSIORTVQH-HOSYLAQJSA-N 0.000 claims description 26
- 239000002253 acid Substances 0.000 claims description 23
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 22
- 150000002924 oxiranes Chemical class 0.000 claims description 20
- 150000003839 salts Chemical class 0.000 claims description 17
- 125000005907 alkyl ester group Chemical group 0.000 claims description 16
- 238000006243 chemical reaction Methods 0.000 claims description 15
- 239000003085 diluting agent Substances 0.000 claims description 15
- 239000004480 active ingredient Substances 0.000 claims description 13
- NFJPEKRRHIYYES-UHFFFAOYSA-N methylidenecyclopentane Chemical class C=C1CCCC1 NFJPEKRRHIYYES-UHFFFAOYSA-N 0.000 claims description 13
- 150000004696 coordination complex Chemical class 0.000 claims description 12
- 150000002148 esters Chemical class 0.000 claims description 11
- JBDSSBMEKXHSJF-UHFFFAOYSA-N cyclopentanecarboxylic acid Chemical compound OC(=O)C1CCCC1 JBDSSBMEKXHSJF-UHFFFAOYSA-N 0.000 claims description 10
- 150000001350 alkyl halides Chemical class 0.000 claims description 8
- 238000006114 decarboxylation reaction Methods 0.000 claims description 8
- NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 claims description 7
- 229910052783 alkali metal Inorganic materials 0.000 claims description 7
- 238000007239 Wittig reaction Methods 0.000 claims description 6
- 150000001340 alkali metals Chemical group 0.000 claims description 6
- FXBPINRBSNMESY-UHFFFAOYSA-N 2-oxocyclopentane-1-carboxylic acid Chemical compound OC(=O)C1CCCC1=O FXBPINRBSNMESY-UHFFFAOYSA-N 0.000 claims description 5
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 5
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 claims description 5
- 238000006735 epoxidation reaction Methods 0.000 claims description 5
- LGRLWUINFJPLSH-UHFFFAOYSA-N methanide Chemical compound [CH3-] LGRLWUINFJPLSH-UHFFFAOYSA-N 0.000 claims description 5
- 230000003301 hydrolyzing effect Effects 0.000 claims description 4
- 125000004429 atom Chemical group 0.000 claims description 2
- 206010017533 Fungal infection Diseases 0.000 claims 1
- 208000031888 Mycoses Diseases 0.000 claims 1
- 239000012044 organic layer Substances 0.000 abstract description 46
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 abstract description 36
- 239000011541 reaction mixture Substances 0.000 abstract description 25
- 238000005406 washing Methods 0.000 abstract description 21
- 238000001816 cooling Methods 0.000 abstract description 18
- 230000012010 growth Effects 0.000 abstract description 17
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract description 14
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 abstract description 8
- 229910000030 sodium bicarbonate Inorganic materials 0.000 abstract description 4
- 235000017557 sodium bicarbonate Nutrition 0.000 abstract description 4
- 238000001035 drying Methods 0.000 abstract description 3
- 230000005764 inhibitory process Effects 0.000 abstract description 3
- 150000007942 carboxylates Chemical class 0.000 abstract description 2
- 125000006527 (C1-C5) alkyl group Chemical group 0.000 abstract 1
- SXDBWCPKPHAZSM-UHFFFAOYSA-N bromic acid Chemical compound OBr(=O)=O SXDBWCPKPHAZSM-UHFFFAOYSA-N 0.000 abstract 1
- 229940093499 ethyl acetate Drugs 0.000 abstract 1
- 235000019439 ethyl acetate Nutrition 0.000 abstract 1
- 239000000463 material Substances 0.000 description 123
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 48
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 27
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 24
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- 239000012312 sodium hydride Substances 0.000 description 22
- 229910000104 sodium hydride Inorganic materials 0.000 description 22
- 230000003595 spectral effect Effects 0.000 description 22
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 20
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
- 239000000543 intermediate Substances 0.000 description 18
- 238000004519 manufacturing process Methods 0.000 description 18
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- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 16
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- 239000000417 fungicide Substances 0.000 description 11
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 10
- 229960001760 dimethyl sulfoxide Drugs 0.000 description 10
- 230000002401 inhibitory effect Effects 0.000 description 10
- 239000004563 wettable powder Substances 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- 239000003795 chemical substances by application Substances 0.000 description 9
- 238000002844 melting Methods 0.000 description 9
- 230000008018 melting Effects 0.000 description 9
- 230000000704 physical effect Effects 0.000 description 9
- 238000010898 silica gel chromatography Methods 0.000 description 9
- 239000001963 growth medium Substances 0.000 description 8
- 238000011835 investigation Methods 0.000 description 8
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- 240000008067 Cucumis sativus Species 0.000 description 7
- 239000011521 glass Substances 0.000 description 7
- 239000001307 helium Substances 0.000 description 7
- 229910052734 helium Inorganic materials 0.000 description 7
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 7
- 238000011081 inoculation Methods 0.000 description 7
- 239000010410 layer Substances 0.000 description 7
- 238000000862 absorption spectrum Methods 0.000 description 6
- 239000002585 base Substances 0.000 description 6
- 125000000753 cycloalkyl group Chemical group 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- 240000005979 Hordeum vulgare Species 0.000 description 5
- 235000007340 Hordeum vulgare Nutrition 0.000 description 5
- 235000014443 Pyrus communis Nutrition 0.000 description 5
- 238000007605 air drying Methods 0.000 description 5
- 125000003710 aryl alkyl group Chemical group 0.000 description 5
- 238000009835 boiling Methods 0.000 description 5
- 235000013399 edible fruits Nutrition 0.000 description 5
- 239000004495 emulsifiable concentrate Substances 0.000 description 5
- 238000000746 purification Methods 0.000 description 5
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- 241001450781 Bipolaris oryzae Species 0.000 description 4
- 241000123650 Botrytis cinerea Species 0.000 description 4
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- 244000068988 Glycine max Species 0.000 description 4
- 235000010469 Glycine max Nutrition 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 235000009754 Vitis X bourquina Nutrition 0.000 description 4
- 235000012333 Vitis X labruscana Nutrition 0.000 description 4
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- 125000003545 alkoxy group Chemical group 0.000 description 4
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- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 4
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- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
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- 241000219310 Beta vulgaris subsp. vulgaris Species 0.000 description 3
- 241000895502 Blumeria graminis f. sp. tritici Species 0.000 description 3
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- 235000015510 Cucumis melo subsp melo Nutrition 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
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- 241000896246 Golovinomyces cichoracearum Species 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
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- YNJSNEKCXVFDKW-UHFFFAOYSA-N 3-(5-amino-1h-indol-3-yl)-2-azaniumylpropanoate Chemical compound C1=C(N)C=C2C(CC(N)C(O)=O)=CNC2=C1 YNJSNEKCXVFDKW-UHFFFAOYSA-N 0.000 description 1
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- 241000251468 Actinopterygii Species 0.000 description 1
- 241000223602 Alternaria alternata Species 0.000 description 1
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- 241000221787 Erysiphe Species 0.000 description 1
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- YZCKVEUIGOORGS-IGMARMGPSA-N Protium Chemical group [1H] YZCKVEUIGOORGS-IGMARMGPSA-N 0.000 description 1
- 235000006040 Prunus persica var persica Nutrition 0.000 description 1
- 241000221301 Puccinia graminis Species 0.000 description 1
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- 241001597349 Septoria glycines Species 0.000 description 1
- 244000061458 Solanum melongena Species 0.000 description 1
- 235000002597 Solanum melongena Nutrition 0.000 description 1
- YZCKVEUIGOORGS-NJFSPNSNSA-N Tritium Chemical group [3H] YZCKVEUIGOORGS-NJFSPNSNSA-N 0.000 description 1
- 241000228452 Venturia inaequalis Species 0.000 description 1
- 241001669638 Venturia nashicola Species 0.000 description 1
- 241000219094 Vitaceae Species 0.000 description 1
- 241000589652 Xanthomonas oryzae Species 0.000 description 1
- 241001360088 Zymoseptoria tritici Species 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
- 229910000102 alkali metal hydride Inorganic materials 0.000 description 1
- 150000008046 alkali metal hydrides Chemical class 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 1
- 125000005530 alkylenedioxy group Chemical group 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 229940121375 antifungal agent Drugs 0.000 description 1
- 125000005160 aryl oxy alkyl group Chemical group 0.000 description 1
- 230000033228 biological regulation Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- UHZZMRAGKVHANO-UHFFFAOYSA-M chlormequat chloride Chemical compound [Cl-].C[N+](C)(C)CCCl UHZZMRAGKVHANO-UHFFFAOYSA-M 0.000 description 1
- 235000020971 citrus fruits Nutrition 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 239000007799 cork Substances 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 238000003912 environmental pollution Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 235000021022 fresh fruits Nutrition 0.000 description 1
- 244000053095 fungal pathogen Species 0.000 description 1
- 244000000004 fungal plant pathogen Species 0.000 description 1
- 230000035784 germination Effects 0.000 description 1
- IXORZMNAPKEEDV-UHFFFAOYSA-N gibberellic acid GA3 Natural products OC(=O)C1C2(C3)CC(=C)C3(O)CCC2C2(C=CC3O)C1C3(C)C(=O)O2 IXORZMNAPKEEDV-UHFFFAOYSA-N 0.000 description 1
- 239000003448 gibberellin Substances 0.000 description 1
- 235000021021 grapes Nutrition 0.000 description 1
- 231100000001 growth retardation Toxicity 0.000 description 1
- 230000002363 herbicidal effect Effects 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 239000002035 hexane extract Substances 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 238000003898 horticulture Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 229940071870 hydroiodic acid Drugs 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 description 1
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 description 1
- QGUHMUXBDNKLNM-UHFFFAOYSA-N methyl 1-[(4-chlorophenyl)methyl]-3,3-dimethyl-2-oxocyclopentane-1-carboxylate Chemical compound C=1C=C(Cl)C=CC=1CC1(C(=O)OC)CCC(C)(C)C1=O QGUHMUXBDNKLNM-UHFFFAOYSA-N 0.000 description 1
- WICVAJZHKHFIAF-UHFFFAOYSA-N methyl 1-[(4-chlorophenyl)methyl]-3-ethyl-3-methyl-2-oxocyclopentane-1-carboxylate Chemical compound O=C1C(CC)(C)CCC1(C(=O)OC)CC1=CC=C(Cl)C=C1 WICVAJZHKHFIAF-UHFFFAOYSA-N 0.000 description 1
- XLXHNYUBTZYEQX-UHFFFAOYSA-N methyl 3-methyl-2-oxocyclopentane-1-carboxylate Chemical compound COC(=O)C1CCC(C)C1=O XLXHNYUBTZYEQX-UHFFFAOYSA-N 0.000 description 1
- LSEFCHWGJNHZNT-UHFFFAOYSA-M methyl(triphenyl)phosphanium;bromide Chemical compound [Br-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(C)C1=CC=CC=C1 LSEFCHWGJNHZNT-UHFFFAOYSA-M 0.000 description 1
- XYDYWTJEGDZLTH-UHFFFAOYSA-N methylenetriphenylphosphorane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)(=C)C1=CC=CC=C1 XYDYWTJEGDZLTH-UHFFFAOYSA-N 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000004967 organic peroxy acids Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000000466 oxiranyl group Chemical group 0.000 description 1
- XNLICIUVMPYHGG-UHFFFAOYSA-N pentan-2-one Chemical compound CCCC(C)=O XNLICIUVMPYHGG-UHFFFAOYSA-N 0.000 description 1
- 230000002093 peripheral effect Effects 0.000 description 1
- 125000002071 phenylalkoxy group Chemical group 0.000 description 1
- 125000003884 phenylalkyl group Chemical group 0.000 description 1
- 239000003375 plant hormone Substances 0.000 description 1
- 239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 description 1
- 235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 1
- 229910000105 potassium hydride Inorganic materials 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 230000000069 prophylactic effect Effects 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 238000013138 pruning Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000000452 restraining effect Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 235000014347 soups Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical group C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- VFJYIHQDILEQNR-UHFFFAOYSA-M trimethylsulfanium;iodide Chemical compound [I-].C[S+](C)C VFJYIHQDILEQNR-UHFFFAOYSA-M 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Epoxy Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP16112687 | 1987-06-30 | ||
| JP62271277A JPH0625140B2 (ja) | 1986-11-10 | 1987-10-27 | 新規アゾール誘導体、その製造方法及び該誘導体の農園芸用薬剤 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE880375L IE880375L (en) | 1988-12-30 |
| IE74147B1 true IE74147B1 (en) | 1997-07-02 |
Family
ID=26487374
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE37588A IE74147B1 (en) | 1987-06-30 | 1988-02-11 | Azole derivatives useful in controlling plant diseases and regulating plant growth |
Country Status (15)
| Country | Link |
|---|---|
| KR (1) | KR900003269B1 (cs) |
| CN (1) | CN1020606C (cs) |
| AR (1) | AR245703A1 (cs) |
| CS (1) | CS274740B2 (cs) |
| GE (1) | GEP19981269B (cs) |
| HU (1) | HU206023B (cs) |
| IE (1) | IE74147B1 (cs) |
| IL (1) | IL85428A (cs) |
| LV (1) | LV10436B (cs) |
| MA (1) | MA21204A1 (cs) |
| MD (1) | MD422C2 (cs) |
| NZ (1) | NZ223444A (cs) |
| RU (1) | RU2047605C1 (cs) |
| TR (1) | TR26948A (cs) |
| UA (1) | UA27101A1 (cs) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BRPI0810236A2 (pt) | 2007-04-25 | 2014-09-30 | Basf Se | Misturas fungicidas, agente fungicida, método para combater fungos nocivos fitopatogênicos, semente, e, uso de compostos. |
| UA108867C2 (uk) * | 2009-12-08 | 2015-06-25 | Похідні азолу, спосіб їх одержання (варіанти), проміжні продукти, засіб для сільського господарства і садівництва | |
| CN102067862A (zh) * | 2011-02-19 | 2011-05-25 | 陕西美邦农药有限公司 | 一种含有种菌唑的杀菌组合物 |
| CN102077839A (zh) * | 2011-03-10 | 2011-06-01 | 陕西美邦农药有限公司 | 一种含有种菌唑与三唑类化合物的杀菌组合物 |
| CN103596934B (zh) * | 2011-05-31 | 2015-08-19 | 株式会社吴羽 | 三氮杂茂化合物、及其运用 |
| US9241488B2 (en) | 2011-06-07 | 2016-01-26 | Kureha Corporation | Azole derivative, method for producing azole derivative, and intermediate compound |
| AU2012268211B2 (en) | 2011-06-07 | 2015-10-15 | Kureha Corporation | Azole derivative, method for producing same, intermediate compound, and agricultural or horticultural chemical agent and industrial material protecting agent |
| CN103764636A (zh) | 2011-06-07 | 2014-04-30 | 株式会社吴羽 | 氧杂环丁烷化合物的制造方法、唑甲基环戊醇化合物的制造方法、以及中间体化合物 |
| WO2013077265A1 (ja) * | 2011-11-25 | 2013-05-30 | 株式会社クレハ | アゾール誘導体、およびその利用 |
| WO2013117629A1 (en) * | 2012-02-10 | 2013-08-15 | Basf Agro B.V., Arnhem (Nl), Zürich-Branch | Process for preparing cis-5-[1-(4-chlorophenyl)-methylene]-1-hydroxymethyl-2,2-dimethylcyclopentanol |
| AU2014358488B2 (en) | 2013-12-05 | 2017-01-12 | Kureha Corporation | Agricultural and horticultural chemical, plant disease control method and plant disease control product |
| EA201690801A1 (ru) | 2013-12-05 | 2016-08-31 | Куреха Корпорейшн | Сельскохозяйственное или садоводческое химическое средство, способ борьбы с болезнями растений и продукт для борьбы с болезнями растений |
| CN104710372B (zh) * | 2013-12-13 | 2017-12-15 | 上海交通大学 | 叶菌唑及其制备方法 |
| CN106243087B (zh) * | 2016-09-12 | 2018-10-09 | 三峡大学 | 一种三唑吡咯烷酮类杀菌剂，合成方法及其应用 |
| CN118146096B (zh) * | 2023-11-20 | 2025-07-11 | 浙江大学 | 一种2,2-二甲基-5-(4-氯苄基)环戊酮衍生物及其制备方法 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4863505A (en) * | 1985-09-12 | 1989-09-05 | Kureha Kagaku Kogyo Kabushiki Kaisha | Novel derivative of azole, and agricultural and horticultural composition containing the same as an active incredient |
-
1988
- 1988-02-08 NZ NZ223444A patent/NZ223444A/xx unknown
- 1988-02-11 IE IE37588A patent/IE74147B1/en not_active IP Right Cessation
- 1988-02-15 IL IL85428A patent/IL85428A/xx not_active IP Right Cessation
- 1988-02-18 CS CS103388A patent/CS274740B2/cs not_active IP Right Cessation
- 1988-02-23 AR AR88310141A patent/AR245703A1/es active
- 1988-02-26 KR KR1019880001977A patent/KR900003269B1/ko not_active Expired
- 1988-02-27 CN CN88101050A patent/CN1020606C/zh not_active Expired - Lifetime
- 1988-03-08 MA MA21445A patent/MA21204A1/fr unknown
- 1988-03-09 UA UA5052494A patent/UA27101A1/uk unknown
- 1988-03-17 TR TR00202/88A patent/TR26948A/xx unknown
- 1988-06-04 HU HU88604A patent/HU206023B/hu unknown
-
1992
- 1992-08-12 RU SU5052494/04A patent/RU2047605C1/ru active
-
1993
- 1993-06-29 LV LVP-93-766A patent/LV10436B/lv unknown
- 1993-07-22 GE GEAP19931110A patent/GEP19981269B/en unknown
-
1994
- 1994-09-01 MD MD95-0292A patent/MD422C2/ro unknown
Also Published As
| Publication number | Publication date |
|---|---|
| MD422C2 (ro) | 1997-04-30 |
| CN1020606C (zh) | 1993-05-12 |
| HU206023B (en) | 1992-08-28 |
| IE880375L (en) | 1988-12-30 |
| LV10436A (lv) | 1995-02-20 |
| CN1030232A (zh) | 1989-01-11 |
| AR245703A1 (es) | 1994-02-28 |
| UA27101A1 (uk) | 2000-02-28 |
| KR900003269B1 (ko) | 1990-05-12 |
| GEP19981269B (en) | 1998-07-07 |
| KR890012981A (ko) | 1989-09-20 |
| IL85428A0 (en) | 1988-07-31 |
| HUT47254A (en) | 1989-02-28 |
| CS103388A2 (en) | 1990-12-13 |
| IL85428A (en) | 1992-12-01 |
| RU2047605C1 (ru) | 1995-11-10 |
| NZ223444A (en) | 1990-06-26 |
| TR26948A (tr) | 1994-09-12 |
| MA21204A1 (fr) | 1988-10-01 |
| LV10436B (en) | 1996-08-20 |
| CS274740B2 (en) | 1991-10-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MK9A | Patent expired |