PL92427B1 - - Google Patents
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- Publication number
- PL92427B1 PL92427B1 PL17669472A PL17669472A PL92427B1 PL 92427 B1 PL92427 B1 PL 92427B1 PL 17669472 A PL17669472 A PL 17669472A PL 17669472 A PL17669472 A PL 17669472A PL 92427 B1 PL92427 B1 PL 92427B1
- Authority
- PL
- Poland
- Prior art keywords
- nitro
- carbon atoms
- formula
- group
- carboxamide
- Prior art date
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- -1 3-nitro-4- (substituted) pyrazoles Chemical class 0.000 claims description 81
- 125000004432 carbon atom Chemical group C* 0.000 claims description 36
- 150000001875 compounds Chemical class 0.000 claims description 30
- 238000002360 preparation method Methods 0.000 claims description 25
- 150000003857 carboxamides Chemical class 0.000 claims description 16
- 238000000034 method Methods 0.000 claims description 10
- 150000003839 salts Chemical class 0.000 claims description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
- MCOJDENHMYYSQV-UHFFFAOYSA-N 5-nitro-1h-pyrazole-4-carboxamide Chemical compound NC(=O)C1=CNN=C1[N+]([O-])=O MCOJDENHMYYSQV-UHFFFAOYSA-N 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 229910052783 alkali metal Inorganic materials 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
- 229910004039 HBF4 Inorganic materials 0.000 claims description 4
- 125000000304 alkynyl group Chemical group 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 4
- 239000012954 diazonium Substances 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 229910052740 iodine Inorganic materials 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- BHWGVDFLAUBWLA-UHFFFAOYSA-N 5-nitro-1h-pyrazole-4-carbonitrile Chemical compound [O-][N+](=O)C=1NN=CC=1C#N BHWGVDFLAUBWLA-UHFFFAOYSA-N 0.000 claims description 3
- 150000001412 amines Chemical class 0.000 claims description 3
- 150000007942 carboxylates Chemical class 0.000 claims description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical compound [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 claims description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical group [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 2
- 125000004414 alkyl thio group Chemical group 0.000 claims description 2
- 125000001589 carboacyl group Chemical group 0.000 claims description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims 2
- 125000004429 atom Chemical group 0.000 claims 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims 2
- 125000004997 halocarbonyl group Chemical group 0.000 claims 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims 2
- VSINDDANNGMBLT-UHFFFAOYSA-N 3ah-isoindole-1,3,4-trione Chemical class C1=CC(=O)C2C(=O)NC(=O)C2=C1 VSINDDANNGMBLT-UHFFFAOYSA-N 0.000 claims 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 claims 1
- 229910000102 alkali metal hydride Inorganic materials 0.000 claims 1
- 150000008046 alkali metal hydrides Chemical class 0.000 claims 1
- 229910000272 alkali metal oxide Inorganic materials 0.000 claims 1
- 150000004678 hydrides Chemical class 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 125000000335 thiazolyl group Chemical group 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 51
- 239000000203 mixture Substances 0.000 description 42
- 125000001424 substituent group Chemical group 0.000 description 26
- 238000002844 melting Methods 0.000 description 25
- 230000008018 melting Effects 0.000 description 25
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 25
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 24
- 239000000243 solution Substances 0.000 description 21
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 14
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 13
- 239000000047 product Substances 0.000 description 13
- 229910052757 nitrogen Inorganic materials 0.000 description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 238000001816 cooling Methods 0.000 description 8
- 239000003921 oil Substances 0.000 description 8
- 235000019198 oils Nutrition 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 7
- 239000000725 suspension Substances 0.000 description 7
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- 239000012043 crude product Substances 0.000 description 6
- 239000007858 starting material Substances 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 description 5
- MZRUFMBFIKGOAL-UHFFFAOYSA-N 5-nitro-1h-pyrazole Chemical group [O-][N+](=O)C1=CC=NN1 MZRUFMBFIKGOAL-UHFFFAOYSA-N 0.000 description 5
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 5
- 239000003153 chemical reaction reagent Substances 0.000 description 5
- 150000002148 esters Chemical class 0.000 description 5
- 239000012044 organic layer Substances 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- 159000000000 sodium salts Chemical class 0.000 description 5
- NJBDBENRPJEIHN-UHFFFAOYSA-N 1-methyl-3-nitropyrazole-4-carbonitrile Chemical compound CN1C=C(C#N)C([N+]([O-])=O)=N1 NJBDBENRPJEIHN-UHFFFAOYSA-N 0.000 description 4
- NUGZBVBZIDWZAD-UHFFFAOYSA-N 1h-pyrazole-4-carbonitrile Chemical compound N#CC=1C=NNC=1 NUGZBVBZIDWZAD-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 125000003342 alkenyl group Chemical group 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- LOIDMDPCSBUPCZ-UHFFFAOYSA-N 1-(2-hydroxyethyl)-3-nitropyrazole-4-carboxamide Chemical compound NC(=O)C1=CN(CCO)N=C1[N+]([O-])=O LOIDMDPCSBUPCZ-UHFFFAOYSA-N 0.000 description 3
- UQRRCAUELNIPJW-UHFFFAOYSA-N 1-(2-hydroxyethyl)-3-nitropyrazole-4-carboxylic acid Chemical compound OCCN1C=C(C(O)=O)C([N+]([O-])=O)=N1 UQRRCAUELNIPJW-UHFFFAOYSA-N 0.000 description 3
- IEWOTEOUUSYKAQ-UHFFFAOYSA-N 1-(2-hydroxyethyl)-n-methyl-3-nitropyrazole-4-carboxamide Chemical compound CNC(=O)C1=CN(CCO)N=C1[N+]([O-])=O IEWOTEOUUSYKAQ-UHFFFAOYSA-N 0.000 description 3
- HZSZGDHAUCLQJY-UHFFFAOYSA-N 1-ethenyl-3-nitropyrazole-4-carboxamide Chemical compound NC(=O)C1=CN(C=C)N=C1[N+]([O-])=O HZSZGDHAUCLQJY-UHFFFAOYSA-N 0.000 description 3
- CYTLOMOEKMHGPM-UHFFFAOYSA-N 1-methyl-3-nitropyrazole-4-carbonyl chloride Chemical compound CN1C=C(C(Cl)=O)C([N+]([O-])=O)=N1 CYTLOMOEKMHGPM-UHFFFAOYSA-N 0.000 description 3
- ZIDNELAAGGUUFP-UHFFFAOYSA-N 1-methyl-3-nitropyrazole-4-carboxamide Chemical compound CN1C=C(C(N)=O)C([N+]([O-])=O)=N1 ZIDNELAAGGUUFP-UHFFFAOYSA-N 0.000 description 3
- BNYCHCAYYYRJSH-UHFFFAOYSA-N 1h-pyrazole-5-carboxamide Chemical compound NC(=O)C1=CC=NN1 BNYCHCAYYYRJSH-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 241000607142 Salmonella Species 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- OSWXMVCQEZDFPI-UHFFFAOYSA-N methyl 1-(2-hydroxyethyl)-3-nitropyrazole-4-carboxylate Chemical compound COC(=O)C1=CN(CCO)N=C1[N+]([O-])=O OSWXMVCQEZDFPI-UHFFFAOYSA-N 0.000 description 3
- 244000045947 parasite Species 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 2
- FGEIVVMHVGMDME-UHFFFAOYSA-N 1-benzyl-3-nitropyrazole-4-carboxamide Chemical compound N1=C([N+]([O-])=O)C(C(=O)N)=CN1CC1=CC=CC=C1 FGEIVVMHVGMDME-UHFFFAOYSA-N 0.000 description 2
- SMXDRRLYXOTORT-UHFFFAOYSA-N 1-methyl-3-nitropyrazole-4-carboxylic acid Chemical compound CN1C=C(C(O)=O)C([N+]([O-])=O)=N1 SMXDRRLYXOTORT-UHFFFAOYSA-N 0.000 description 2
- ZVXKYWHJBYIYNI-UHFFFAOYSA-N 1h-pyrazole-4-carboxamide Chemical compound NC(=O)C=1C=NNC=1 ZVXKYWHJBYIYNI-UHFFFAOYSA-N 0.000 description 2
- 125000005999 2-bromoethyl group Chemical group 0.000 description 2
- MRJYTCKHIMHUMK-UHFFFAOYSA-N 3-nitro-1-nonylpyrazole-4-carboxamide Chemical compound CCCCCCCCCN1C=C(C(N)=O)C([N+]([O-])=O)=N1 MRJYTCKHIMHUMK-UHFFFAOYSA-N 0.000 description 2
- JIRJTQLEIXUBGJ-UHFFFAOYSA-N 3-nitro-1-propylpyrazole-4-carboxamide Chemical compound CCCN1C=C(C(N)=O)C([N+]([O-])=O)=N1 JIRJTQLEIXUBGJ-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 241000589877 Campylobacter coli Species 0.000 description 2
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical group NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- 241000588724 Escherichia coli Species 0.000 description 2
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- 241000204031 Mycoplasma Species 0.000 description 2
- 241001579016 Nanoa Species 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 241000392514 Salmonella enterica subsp. enterica serovar Dublin Species 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 125000004423 acyloxy group Chemical group 0.000 description 2
- 230000004071 biological effect Effects 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 229940023064 escherichia coli Drugs 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 230000002363 herbicidal effect Effects 0.000 description 2
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 239000010410 layer Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- YJOLQLMJAZKELN-UHFFFAOYSA-N methyl 1-methyl-3-nitropyrazole-4-carboxylate Chemical compound COC(=O)C1=CN(C)N=C1[N+]([O-])=O YJOLQLMJAZKELN-UHFFFAOYSA-N 0.000 description 2
- 244000005700 microbiome Species 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 150000002825 nitriles Chemical class 0.000 description 2
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 125000003226 pyrazolyl group Chemical group 0.000 description 2
- 239000013049 sediment Substances 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- 238000007039 two-step reaction Methods 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- UVROAJFELBNMRA-UHFFFAOYSA-N (1-chloro-2-phenylethyl)benzene Chemical compound C=1C=CC=CC=1C(Cl)CC1=CC=CC=C1 UVROAJFELBNMRA-UHFFFAOYSA-N 0.000 description 1
- NDQXKKFRNOPRDW-UHFFFAOYSA-N 1,1,1-triethoxyethane Chemical compound CCOC(C)(OCC)OCC NDQXKKFRNOPRDW-UHFFFAOYSA-N 0.000 description 1
- JDAOVAPWRGYBQR-UHFFFAOYSA-N 1-(2,2-diethoxyethyl)-3-nitropyrazole-4-carboxamide Chemical compound CCOC(OCC)CN1C=C(C(N)=O)C([N+]([O-])=O)=N1 JDAOVAPWRGYBQR-UHFFFAOYSA-N 0.000 description 1
- MLQGOONHCMTHNW-UHFFFAOYSA-N 1-(2-bromoethyl)-3-nitropyrazole-4-carboxamide Chemical compound NC(=O)C1=CN(CCBr)N=C1[N+]([O-])=O MLQGOONHCMTHNW-UHFFFAOYSA-N 0.000 description 1
- HNBISZHHRQNLLY-UHFFFAOYSA-N 1-(2-chloroethyl)-3-nitropyrazole-4-carbonitrile Chemical compound [O-][N+](=O)C1=NN(CCCl)C=C1C#N HNBISZHHRQNLLY-UHFFFAOYSA-N 0.000 description 1
- RKYBOGMRSVFVFN-UHFFFAOYSA-N 1-(2-chloroethyl)-3-nitropyrazole-4-carboxamide Chemical compound NC(=O)C1=CN(CCCl)N=C1[N+]([O-])=O RKYBOGMRSVFVFN-UHFFFAOYSA-N 0.000 description 1
- MZUVBFSJVZYWTC-UHFFFAOYSA-N 1-(2-ethoxyethyl)-3-nitropyrazole-4-carbonitrile Chemical compound CCOCCN1C=C(C#N)C([N+]([O-])=O)=N1 MZUVBFSJVZYWTC-UHFFFAOYSA-N 0.000 description 1
- WECOGUIVFJUKOT-UHFFFAOYSA-N 1-(2-ethoxyethyl)-3-nitropyrazole-4-carboxamide Chemical compound CCOCCN1C=C(C(N)=O)C([N+]([O-])=O)=N1 WECOGUIVFJUKOT-UHFFFAOYSA-N 0.000 description 1
- YLXSGUIBKJNWDR-UHFFFAOYSA-N 1-(2-ethylsulfonylethyl)-3-nitropyrazole-4-carboxamide Chemical compound CCS(=O)(=O)CCN1C=C(C(N)=O)C([N+]([O-])=O)=N1 YLXSGUIBKJNWDR-UHFFFAOYSA-N 0.000 description 1
- CHDFUJJHFZBNFQ-UHFFFAOYSA-N 1-(3-chloro-2-hydroxypropyl)-3-nitropyrazole-4-carbonitrile Chemical compound ClCC(O)CN1C=C(C#N)C([N+]([O-])=O)=N1 CHDFUJJHFZBNFQ-UHFFFAOYSA-N 0.000 description 1
- HSHFZKZJRBPBIZ-UHFFFAOYSA-N 1-(3-chloropropyl)-3-nitropyrazole-4-carbonitrile Chemical compound [O-][N+](=O)C1=NN(CCCCl)C=C1C#N HSHFZKZJRBPBIZ-UHFFFAOYSA-N 0.000 description 1
- ZYEVBSQPKWNECH-UHFFFAOYSA-N 1-(3-methylpentan-2-yl)-3-nitropyrazole-4-carboxamide Chemical compound CCC(C)C(C)N1C=C(C(N)=O)C([N+]([O-])=O)=N1 ZYEVBSQPKWNECH-UHFFFAOYSA-N 0.000 description 1
- NWRLRHHJJOIGFN-UHFFFAOYSA-N 1-[2-(1,3-dioxoisoindol-2-yl)ethyl]-3-nitropyrazole-4-carboxamide Chemical compound N1=C([N+]([O-])=O)C(C(=O)N)=CN1CCN1C(=O)C2=CC=CC=C2C1=O NWRLRHHJJOIGFN-UHFFFAOYSA-N 0.000 description 1
- MKHBODRSULWFMJ-UHFFFAOYSA-N 1-benzyl-3-nitropyrazole-4-carbonitrile Chemical compound C1=C(C#N)C([N+](=O)[O-])=NN1CC1=CC=CC=C1 MKHBODRSULWFMJ-UHFFFAOYSA-N 0.000 description 1
- WKXAEFOKLDCKHX-UHFFFAOYSA-N 1-but-2-enyl-3-nitropyrazole-4-carboxamide Chemical compound CC=CCN1C=C(C(N)=O)C([N+]([O-])=O)=N1 WKXAEFOKLDCKHX-UHFFFAOYSA-N 0.000 description 1
- VDFPLBHYELEAKI-UHFFFAOYSA-N 1-ethyl-3-nitropyrazole-4-carboxylic acid Chemical compound CCN1C=C(C(O)=O)C([N+]([O-])=O)=N1 VDFPLBHYELEAKI-UHFFFAOYSA-N 0.000 description 1
- WFQDTOYDVUWQMS-UHFFFAOYSA-N 1-fluoro-4-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(F)C=C1 WFQDTOYDVUWQMS-UHFFFAOYSA-N 0.000 description 1
- 125000004343 1-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C([H])([H])[H] 0.000 description 1
- YMJLEPMVGQBLHL-UHFFFAOYSA-N 1h-pyrazole-5-carbonitrile Chemical compound N#CC1=CC=NN1 YMJLEPMVGQBLHL-UHFFFAOYSA-N 0.000 description 1
- RQUBFCKHWLKLRV-UHFFFAOYSA-N 2-(1-ethoxybutylidene)propanedinitrile Chemical compound CCCC(OCC)=C(C#N)C#N RQUBFCKHWLKLRV-UHFFFAOYSA-N 0.000 description 1
- GXMOSBIOUZALPM-UHFFFAOYSA-N 2-(1-ethoxypropylidene)propanedinitrile Chemical compound CCOC(CC)=C(C#N)C#N GXMOSBIOUZALPM-UHFFFAOYSA-N 0.000 description 1
- APYUMVPJPKDCKN-UHFFFAOYSA-N 2-(4-carbamoyl-3-nitropyrazol-1-yl)ethyl 4-ethylbenzoate Chemical compound C1=CC(CC)=CC=C1C(=O)OCCN1N=C([N+]([O-])=O)C(C(N)=O)=C1 APYUMVPJPKDCKN-UHFFFAOYSA-N 0.000 description 1
- YLJPIHCSEKMQNU-UHFFFAOYSA-N 2-(4-carbamoyl-3-nitropyrazol-1-yl)ethyl acetate Chemical compound CC(=O)OCCN1C=C(C(N)=O)C([N+]([O-])=O)=N1 YLJPIHCSEKMQNU-UHFFFAOYSA-N 0.000 description 1
- RPDOYSCEKPNPLZ-UHFFFAOYSA-N 2-bromo-1,3,5-triazine Chemical compound BrC1=NC=NC=N1 RPDOYSCEKPNPLZ-UHFFFAOYSA-N 0.000 description 1
- LDLCZOVUSADOIV-UHFFFAOYSA-N 2-bromoethanol Chemical compound OCCBr LDLCZOVUSADOIV-UHFFFAOYSA-N 0.000 description 1
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 1
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
- 125000005917 3-methylpentyl group Chemical group 0.000 description 1
- VGKDKJGNGNLEDI-UHFFFAOYSA-N 3-nitro-1-(2-oxopropyl)pyrazole-4-carboxamide Chemical compound CC(=O)CN1C=C(C(N)=O)C([N+]([O-])=O)=N1 VGKDKJGNGNLEDI-UHFFFAOYSA-N 0.000 description 1
- JBLFABWDCCQTOJ-UHFFFAOYSA-N 3-nitro-1-(4-nitrophenyl)pyrazole-4-carbonitrile Chemical compound C1=C(C#N)C([N+](=O)[O-])=NN1C1=CC=C([N+]([O-])=O)C=C1 JBLFABWDCCQTOJ-UHFFFAOYSA-N 0.000 description 1
- LLVAYQKWGGWHLN-UHFFFAOYSA-N 3-nitro-1-(4-nitrophenyl)pyrazole-4-carboxamide Chemical compound N1=C([N+]([O-])=O)C(C(=O)N)=CN1C1=CC=C([N+]([O-])=O)C=C1 LLVAYQKWGGWHLN-UHFFFAOYSA-N 0.000 description 1
- RJYISCPTPFJFJT-UHFFFAOYSA-N 3-nitro-1-(oxiran-2-ylmethyl)pyrazole-4-carbonitrile Chemical compound C1=C(C#N)C([N+](=O)[O-])=NN1CC1OC1 RJYISCPTPFJFJT-UHFFFAOYSA-N 0.000 description 1
- XEFALKUTCMBSNA-UHFFFAOYSA-N 3-nitro-1-(oxiran-2-ylmethyl)pyrazole-4-carboxamide Chemical compound N1=C([N+]([O-])=O)C(C(=O)N)=CN1CC1OC1 XEFALKUTCMBSNA-UHFFFAOYSA-N 0.000 description 1
- IMBBXSASDSZJSX-UHFFFAOYSA-N 4-Carboxypyrazole Chemical class OC(=O)C=1C=NNC=1 IMBBXSASDSZJSX-UHFFFAOYSA-N 0.000 description 1
- SXIFAEWFOJETOA-UHFFFAOYSA-N 4-hydroxy-butyl Chemical group [CH2]CCCO SXIFAEWFOJETOA-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- 241000271566 Aves Species 0.000 description 1
- 241000123650 Botrytis cinerea Species 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 1
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 1
- 241000588694 Erwinia amylovora Species 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 241000287828 Gallus gallus Species 0.000 description 1
- 241000948219 Histomonas Species 0.000 description 1
- 241000948220 Histomonas meleagridis Species 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 229930194542 Keto Natural products 0.000 description 1
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 241000204022 Mycoplasma gallisepticum Species 0.000 description 1
- 239000004677 Nylon Substances 0.000 description 1
- 235000019502 Orange oil Nutrition 0.000 description 1
- 229910020667 PBr3 Inorganic materials 0.000 description 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical class ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 241000589516 Pseudomonas Species 0.000 description 1
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 1
- 241000283984 Rodentia Species 0.000 description 1
- 241000191940 Staphylococcus Species 0.000 description 1
- 241000191967 Staphylococcus aureus Species 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- 241000224526 Trichomonas Species 0.000 description 1
- 241000223109 Trypanosoma cruzi Species 0.000 description 1
- 241000082085 Verticillium <Phyllachorales> Species 0.000 description 1
- OCBFFGCSTGGPSQ-UHFFFAOYSA-N [CH2]CC Chemical compound [CH2]CC OCBFFGCSTGGPSQ-UHFFFAOYSA-N 0.000 description 1
- UGAPHEBNTGUMBB-UHFFFAOYSA-N acetic acid;ethyl acetate Chemical compound CC(O)=O.CCOC(C)=O UGAPHEBNTGUMBB-UHFFFAOYSA-N 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 230000003213 activating effect Effects 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 229910001508 alkali metal halide Inorganic materials 0.000 description 1
- 150000008045 alkali metal halides Chemical class 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N alpha-methyl toluene Natural products CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 239000004599 antimicrobial Substances 0.000 description 1
- 150000005840 aryl radicals Chemical class 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- 239000012455 biphasic mixture Substances 0.000 description 1
- 239000012267 brine 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
- 125000005392 carboxamide group Chemical group NC(=O)* 0.000 description 1
- 125000005518 carboxamido group Chemical group 0.000 description 1
- 235000013330 chicken meat Nutrition 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000001989 diazonium salts Chemical class 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical compound C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 229910003480 inorganic solid Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- 125000000468 ketone group Chemical group 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
- BQUGWUGTCZTFCP-UHFFFAOYSA-N n,1-dimethyl-3-nitropyrazole-4-carboxamide Chemical compound CNC(=O)C1=CN(C)N=C1[N+]([O-])=O BQUGWUGTCZTFCP-UHFFFAOYSA-N 0.000 description 1
- DHSFROXREREDKC-UHFFFAOYSA-N n-butyl-1-(2-hydroxyethyl)-3-nitropyrazole-4-carboxamide Chemical compound CCCCNC(=O)C1=CN(CCO)N=C1[N+]([O-])=O DHSFROXREREDKC-UHFFFAOYSA-N 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 231100000956 nontoxicity Toxicity 0.000 description 1
- 229920001778 nylon Polymers 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
- 239000010502 orange oil Substances 0.000 description 1
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- IPNPIHIZVLFAFP-UHFFFAOYSA-N phosphorus tribromide Chemical compound BrP(Br)Br IPNPIHIZVLFAFP-UHFFFAOYSA-N 0.000 description 1
- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 description 1
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- YORCIIVHUBAYBQ-UHFFFAOYSA-N propargyl bromide Chemical compound BrCC#C YORCIIVHUBAYBQ-UHFFFAOYSA-N 0.000 description 1
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 description 1
- 229940080818 propionamide Drugs 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 150000003217 pyrazoles Chemical class 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- XMVJITFPVVRMHC-UHFFFAOYSA-N roxarsone Chemical group OC1=CC=C([As](O)(O)=O)C=C1[N+]([O-])=O XMVJITFPVVRMHC-UHFFFAOYSA-N 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 238000006748 scratching Methods 0.000 description 1
- 230000002393 scratching effect Effects 0.000 description 1
- 239000010802 sludge Substances 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 210000001835 viscera Anatomy 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
Landscapes
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US12446371A | 1971-03-15 | 1971-03-15 | |
| US21179171A | 1971-12-23 | 1971-12-23 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PL92427B1 true PL92427B1 (en:Method) | 1977-04-30 |
Family
ID=26822622
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL17669472A PL92427B1 (en:Method) | 1971-03-15 | 1972-03-15 |
Country Status (8)
| Country | Link |
|---|---|
| AR (2) | AR208267A1 (en:Method) |
| DD (1) | DD97200A5 (en:Method) |
| DK (1) | DK134285B (en:Method) |
| ES (1) | ES400714A1 (en:Method) |
| IE (1) | IE36144B1 (en:Method) |
| IL (1) | IL38950A (en:Method) |
| PL (1) | PL92427B1 (en:Method) |
| RO (1) | RO64927A (en:Method) |
-
1972
- 1972-01-01 AR AR24094672A patent/AR208267A1/es active
- 1972-03-08 IE IE29772A patent/IE36144B1/xx unknown
- 1972-03-10 IL IL38950A patent/IL38950A/en unknown
- 1972-03-13 ES ES400714A patent/ES400714A1/es not_active Expired
- 1972-03-15 DD DD16153772A patent/DD97200A5/xx unknown
- 1972-03-15 PL PL17669472A patent/PL92427B1/pl unknown
- 1972-03-15 RO RO7777772A patent/RO64927A/ro unknown
- 1972-03-15 DK DK120672A patent/DK134285B/da unknown
-
1973
- 1973-11-15 AR AR25101173A patent/AR209267A1/es active
Also Published As
| Publication number | Publication date |
|---|---|
| DD97200A5 (en:Method) | 1973-04-20 |
| AR208267A1 (es) | 1976-12-20 |
| AR209267A1 (es) | 1977-04-15 |
| DK134285C (en:Method) | 1977-03-21 |
| DK134285B (da) | 1976-10-11 |
| IE36144B1 (en) | 1976-09-01 |
| IL38950A0 (en) | 1972-05-30 |
| IL38950A (en) | 1976-07-30 |
| IE36144L (en) | 1972-09-15 |
| ES400714A1 (es) | 1975-01-16 |
| RO64927A (fr) | 1979-03-15 |
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