SK160988A3 - Biocidal agent - Google Patents

Biocidal agent Download PDF

Info

Publication number: SK160988A3
Authority: SK; Slovakia
Prior art keywords: group; compound; cyano; alkyl; phenyl
Prior art date: 1987-03-13

Application number

SK1609-88A

Other languages

English (en)

Slovak (sk)

Other versions

SK278722B6 (sk

Inventor

Rikuo Nasu

Terumasa Komyoji

Kazumi Suzuki

Toshio Nakajima

Keiichiro Ito

Takeshi Ohshima

Hideshi Yoshimura

Original Assignee

Ishihara Sangyo Kaisha

Priority date (The priority date 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 date listed.)

1987-03-13

Filing date

1988-03-11

Publication date

1998-01-14

1988-03-11 Application filed by Ishihara Sangyo Kaisha filed Critical Ishihara Sangyo Kaisha

1998-01-14 Publication of SK278722B6 publication Critical patent/SK278722B6/sk

1998-01-14 Publication of SK160988A3 publication Critical patent/SK160988A3/sk

Links

239000003139 biocide Substances 0.000 title abstract 2
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 41
125000005843 halogen group Chemical group 0.000 claims abstract description 17
150000002460 imidazoles Chemical class 0.000 claims abstract description 12
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 8
125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 8
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 8
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 4
125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims abstract description 3
125000001624 naphthyl group Chemical group 0.000 claims abstract 2
125000001544 thienyl group Chemical group 0.000 claims abstract 2
239000000203 mixture Substances 0.000 claims description 85
125000000217 alkyl group Chemical group 0.000 claims description 10
125000004432 carbon atom Chemical group C* 0.000 claims description 9
229910052736 halogen Inorganic materials 0.000 claims description 7
230000003115 biocidal effect Effects 0.000 claims description 6
150000002367 halogens Chemical class 0.000 claims description 5
239000004480 active ingredient Substances 0.000 claims description 4
125000004414 alkyl thio group Chemical group 0.000 claims 2
125000003342 alkenyl group Chemical group 0.000 claims 1
150000001875 compounds Chemical class 0.000 abstract description 168
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract description 9
229910052757 nitrogen Inorganic materials 0.000 abstract description 7
125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract description 4
125000000882 C2-C6 alkenyl group Chemical group 0.000 abstract description 4
125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 abstract description 4
125000006656 (C2-C4) alkenyl group Chemical group 0.000 abstract description 3
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 abstract description 3
125000004400 (C1-C12) alkyl group Chemical group 0.000 abstract description 2
125000006374 C2-C10 alkenyl group Chemical group 0.000 abstract description 2
125000004076 pyridyl group Chemical group 0.000 abstract 2
125000004191 (C1-C6) alkoxy group Chemical group 0.000 abstract 1
125000002541 furyl group Chemical group 0.000 abstract 1
125000004433 nitrogen atom Chemical group N* 0.000 abstract 1
125000003386 piperidinyl group Chemical group 0.000 abstract 1
125000000719 pyrrolidinyl group Chemical group 0.000 abstract 1
125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 abstract 1
125000005505 thiomorpholino group Chemical group 0.000 abstract 1
125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 abstract 1
-1 substituent hydrogen Chemical class 0.000 description 113
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 105
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 99
239000000460 chlorine Substances 0.000 description 55
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 52
239000000243 solution Substances 0.000 description 45
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 42
238000006243 chemical reaction Methods 0.000 description 40
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 36
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 33
239000011541 reaction mixture Substances 0.000 description 33
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 32
241000196324 Embryophyta Species 0.000 description 31
239000002904 solvent Substances 0.000 description 31
239000003480 eluent Substances 0.000 description 29
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 27
238000010898 silica gel chromatography Methods 0.000 description 27
239000000284 extract Substances 0.000 description 26
238000002844 melting Methods 0.000 description 24
230000008018 melting Effects 0.000 description 24
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 23
201000010099 disease Diseases 0.000 description 20
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 20
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 19
230000033228 biological regulation Effects 0.000 description 18
239000000543 intermediate Substances 0.000 description 17
238000000034 method Methods 0.000 description 17
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 16
230000015572 biosynthetic process Effects 0.000 description 16
238000010992 reflux Methods 0.000 description 16
238000003786 synthesis reaction Methods 0.000 description 16
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 16
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 14
240000008067 Cucumis sativus Species 0.000 description 14
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 14
229920003171 Poly (ethylene oxide) Polymers 0.000 description 14
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 14
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
239000004698 Polyethylene Substances 0.000 description 12
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
239000004615 ingredient Substances 0.000 description 12
229920000573 polyethylene Polymers 0.000 description 12
239000000843 powder Substances 0.000 description 12
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 11
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 11
229910000027 potassium carbonate Inorganic materials 0.000 description 11
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 10
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 10
230000003449 preventive effect Effects 0.000 description 10
241000233866 Fungi Species 0.000 description 9
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
229940079865 intestinal antiinfectives imidazole derivative Drugs 0.000 description 9
JFCHSQDLLFJHOA-UHFFFAOYSA-N n,n-dimethylsulfamoyl chloride Chemical compound CN(C)S(Cl)(=O)=O JFCHSQDLLFJHOA-UHFFFAOYSA-N 0.000 description 9
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 9
239000007787 solid Substances 0.000 description 9
239000004563 wettable powder Substances 0.000 description 9
239000005995 Aluminium silicate Substances 0.000 description 8
235000012211 aluminium silicate Nutrition 0.000 description 8
239000000969 carrier Substances 0.000 description 8
229910052801 chlorine Inorganic materials 0.000 description 8
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 8
238000011081 inoculation Methods 0.000 description 8
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 8
239000007921 spray Substances 0.000 description 8
125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 7
125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 7
235000009849 Cucumis sativus Nutrition 0.000 description 7
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
240000007594 Oryza sativa Species 0.000 description 7
240000003768 Solanum lycopersicum Species 0.000 description 7
229910000019 calcium carbonate Inorganic materials 0.000 description 7
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 7
230000000694 effects Effects 0.000 description 7
230000003902 lesion Effects 0.000 description 7
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 7
239000000725 suspension Substances 0.000 description 7
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 6
125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 6
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 6
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 6
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 6
239000005909 Kieselgur Substances 0.000 description 6
JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 description 6
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 6
230000001143 conditioned effect Effects 0.000 description 6
238000001816 cooling Methods 0.000 description 6
125000002883 imidazolyl group Chemical group 0.000 description 6
239000002689 soil Substances 0.000 description 6
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 6
239000008096 xylene Substances 0.000 description 6
241000238631 Hexapoda Species 0.000 description 5
235000007688 Lycopersicon esculentum Nutrition 0.000 description 5
241001281805 Pseudoperonospora cubensis Species 0.000 description 5
PPKXEPBICJTCRU-UHFFFAOYSA-N [2-hydroxy-2-(3-methoxyphenyl)cyclohexyl]methyl-dimethylazanium;chloride Chemical compound Cl.COC1=CC=CC(C2(O)C(CCCC2)CN(C)C)=C1 PPKXEPBICJTCRU-UHFFFAOYSA-N 0.000 description 5
150000001346 alkyl aryl ethers Chemical class 0.000 description 5
QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 5
239000000440 bentonite Substances 0.000 description 5
229910000278 bentonite Inorganic materials 0.000 description 5
SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 5
229910052794 bromium Inorganic materials 0.000 description 5
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 5
235000013601 eggs Nutrition 0.000 description 5
239000004495 emulsifiable concentrate Substances 0.000 description 5
239000008187 granular material Substances 0.000 description 5
229910052739 hydrogen Inorganic materials 0.000 description 5
230000001939 inductive effect Effects 0.000 description 5
230000003151 ovacidal effect Effects 0.000 description 5
239000000546 pharmaceutical excipient Substances 0.000 description 5
125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 5
238000002360 preparation method Methods 0.000 description 5
229920005552 sodium lignosulfonate Polymers 0.000 description 5
238000003756 stirring Methods 0.000 description 5
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 4
DNYQVSBOGCMIDZ-UHFFFAOYSA-N 4-chloro-2-cyano-n,n-dimethyl-5-phenylimidazole-1-sulfonamide Chemical compound CN(C)S(=O)(=O)N1C(C#N)=NC(Cl)=C1C1=CC=CC=C1 DNYQVSBOGCMIDZ-UHFFFAOYSA-N 0.000 description 4
LXYMZTOFYGBUAB-UHFFFAOYSA-N 4-chloro-2-cyano-n,n-dimethyl-5-propylimidazole-1-sulfonamide Chemical compound CCCC1=C(Cl)N=C(C#N)N1S(=O)(=O)N(C)C LXYMZTOFYGBUAB-UHFFFAOYSA-N 0.000 description 4
241000238876 Acari Species 0.000 description 4
229920001817 Agar Polymers 0.000 description 4
244000075850 Avena orientalis Species 0.000 description 4
235000007319 Avena orientalis Nutrition 0.000 description 4
240000007124 Brassica oleracea Species 0.000 description 4
235000003899 Brassica oleracea var acephala Nutrition 0.000 description 4
235000011301 Brassica oleracea var capitata Nutrition 0.000 description 4
235000001169 Brassica oleracea var oleracea Nutrition 0.000 description 4
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
GUUVPOWQJOLRAS-UHFFFAOYSA-N Diphenyl disulfide Chemical compound C=1C=CC=CC=1SSC1=CC=CC=C1 GUUVPOWQJOLRAS-UHFFFAOYSA-N 0.000 description 4
ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 4
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 4
235000007164 Oryza sativa Nutrition 0.000 description 4
229910019142 PO4 Inorganic materials 0.000 description 4
244000046052 Phaseolus vulgaris Species 0.000 description 4
241001454293 Tetranychus urticae Species 0.000 description 4
239000008272 agar Substances 0.000 description 4
125000002877 alkyl aryl group Chemical group 0.000 description 4
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 4
239000004359 castor oil Substances 0.000 description 4
235000019438 castor oil Nutrition 0.000 description 4
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
229940125782 compound 2 Drugs 0.000 description 4
239000002285 corn oil Substances 0.000 description 4
235000005687 corn oil Nutrition 0.000 description 4
238000001035 drying Methods 0.000 description 4
239000000706 filtrate Substances 0.000 description 4
ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 4
239000001257 hydrogen Substances 0.000 description 4
230000005764 inhibitory process Effects 0.000 description 4
125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 4
125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 4
239000010452 phosphate Substances 0.000 description 4
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 4
239000000047 product Substances 0.000 description 4
150000003254 radicals Chemical class 0.000 description 4
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229910052708 sodium Inorganic materials 0.000 description 4
239000011734 sodium Substances 0.000 description 4
229910021653 sulphate ion Inorganic materials 0.000 description 4
239000004546 suspension concentrate Substances 0.000 description 4
230000009105 vegetative growth Effects 0.000 description 4
QMQZIXCNLUPEIN-UHFFFAOYSA-N 1h-imidazole-2-carbonitrile Chemical compound N#CC1=NC=CN1 QMQZIXCNLUPEIN-UHFFFAOYSA-N 0.000 description 3
UXLNYPNPQJRFJI-UHFFFAOYSA-N 2-cyano-n,n-dimethylimidazole-1-sulfonamide Chemical compound CN(C)S(=O)(=O)N1C=CN=C1C#N UXLNYPNPQJRFJI-UHFFFAOYSA-N 0.000 description 3
125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 description 3
125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 3
125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 description 3
125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 description 3
OETJULOEFJGFJU-UHFFFAOYSA-N 4-chloro-1-(dimethylsulfamoyl)-5-propylimidazole-2-carbothioamide Chemical compound CCCC1=C(Cl)N=C(C(N)=S)N1S(=O)(=O)N(C)C OETJULOEFJGFJU-UHFFFAOYSA-N 0.000 description 3
CPDRSWSOOCBQSY-UHFFFAOYSA-N 4-chloro-2-cyano-n,n-dimethyl-5-propan-2-ylimidazole-1-sulfonamide Chemical compound CC(C)C1=C(Cl)N=C(C#N)N1S(=O)(=O)N(C)C CPDRSWSOOCBQSY-UHFFFAOYSA-N 0.000 description 3
SGNCOJFDRWPOTB-UHFFFAOYSA-N 4-chloro-5-(4-chlorophenyl)-2-cyano-n,n-dimethylimidazole-1-sulfonamide Chemical compound CN(C)S(=O)(=O)N1C(C#N)=NC(Cl)=C1C1=CC=C(Cl)C=C1 SGNCOJFDRWPOTB-UHFFFAOYSA-N 0.000 description 3
125000004861 4-isopropyl phenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 3
SBYMHBPDHMDGJR-UHFFFAOYSA-N 5-chloro-4-(4-chlorophenyl)-2-cyano-n,n-dimethylimidazole-1-sulfonamide Chemical compound N1=C(C#N)N(S(=O)(=O)N(C)C)C(Cl)=C1C1=CC=C(Cl)C=C1 SBYMHBPDHMDGJR-UHFFFAOYSA-N 0.000 description 3
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 3
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 3
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 3
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
241001330975 Magnaporthe oryzae Species 0.000 description 3
241000721621 Myzus persicae Species 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
241001123561 Puccinia coronata Species 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
244000061456 Solanum tuberosum Species 0.000 description 3
235000002595 Solanum tuberosum Nutrition 0.000 description 3
241000985245 Spodoptera litura Species 0.000 description 3
ULUAUXLGCMPNKK-UHFFFAOYSA-N Sulfobutanedioic acid Chemical class OC(=O)CC(C(O)=O)S(O)(=O)=O ULUAUXLGCMPNKK-UHFFFAOYSA-N 0.000 description 3
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 3
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235000012343 cottonseed oil Nutrition 0.000 description 1
239000002385 cottonseed oil Substances 0.000 description 1
239000012043 crude product Substances 0.000 description 1
239000002178 crystalline material Substances 0.000 description 1
125000004802 cyanophenyl group Chemical group 0.000 description 1
125000004122 cyclic group Chemical group 0.000 description 1
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 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
238000010586 diagram Methods 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 1
239000012990 dithiocarbamate Substances 0.000 description 1
150000004659 dithiocarbamates Chemical class 0.000 description 1
239000002552 dosage form Substances 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
210000000744 eyelid Anatomy 0.000 description 1
210000003746 feather Anatomy 0.000 description 1
239000004467 fishmeal Substances 0.000 description 1
235000013312 flour Nutrition 0.000 description 1
125000006005 fluoroethoxy group Chemical group 0.000 description 1
239000010200 folin Substances 0.000 description 1
230000002538 fungal effect Effects 0.000 description 1
239000007789 gas Substances 0.000 description 1
150000008282 halocarbons Chemical class 0.000 description 1
230000012447 hatching Effects 0.000 description 1
125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000004009 herbicide Substances 0.000 description 1
201000008110 hereditary spherocytosis type 3 Diseases 0.000 description 1
125000005842 heteroatom Chemical group 0.000 description 1
239000010903 husk Substances 0.000 description 1
229910000037 hydrogen sulfide Inorganic materials 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
125000004857 imidazopyridinyl group Chemical class N1C(=NC2=C1C=CC=N2)* 0.000 description 1
238000011534 incubation Methods 0.000 description 1
208000015181 infectious disease Diseases 0.000 description 1
239000002054 inoculum Substances 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
238000002955 isolation Methods 0.000 description 1
229930014550 juvenile hormone Chemical class 0.000 description 1
239000002949 juvenile hormone Chemical class 0.000 description 1
150000003633 juvenile hormone derivatives Chemical class 0.000 description 1
239000010410 layer Substances 0.000 description 1
229940057995 liquid paraffin Drugs 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
230000007774 longterm Effects 0.000 description 1
235000012054 meals Nutrition 0.000 description 1
235000013336 milk Nutrition 0.000 description 1
239000008267 milk Substances 0.000 description 1
210000004080 milk Anatomy 0.000 description 1
239000011707 mineral Substances 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
XONPDZSGENTBNJ-UHFFFAOYSA-N molecular hydrogen;sodium Chemical compound [Na].[H][H] XONPDZSGENTBNJ-UHFFFAOYSA-N 0.000 description 1
150000002780 morpholines Chemical class 0.000 description 1
FGCRCMDCHKTIHX-UHFFFAOYSA-N n-[4-chloro-1-(dimethylsulfamoyl)-5-propylimidazole-2-carbothioyl]propanamide Chemical compound CCCC1=C(Cl)N=C(C(=S)NC(=O)CC)N1S(=O)(=O)N(C)C FGCRCMDCHKTIHX-UHFFFAOYSA-N 0.000 description 1
125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
239000005645 nematicide Substances 0.000 description 1
238000006386 neutralization reaction Methods 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
125000001400 nonyl 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])C([H])([H])[H] 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
150000002898 organic sulfur compounds Chemical class 0.000 description 1
150000002902 organometallic compounds Chemical class 0.000 description 1
231100000194 ovacidal Toxicity 0.000 description 1
230000017448 oviposition Effects 0.000 description 1
230000001717 pathogenic effect Effects 0.000 description 1
125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 1
239000003444 phase transfer catalyst Substances 0.000 description 1
125000004344 phenylpropyl group Chemical group 0.000 description 1
125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 1
239000005648 plant growth regulator Substances 0.000 description 1
239000002798 polar solvent Substances 0.000 description 1
229920000259 polyoxyethylene lauryl ether Polymers 0.000 description 1
239000004302 potassium sorbate Substances 0.000 description 1
235000012015 potatoes Nutrition 0.000 description 1
239000012254 powdered material Substances 0.000 description 1
238000004262 preparative liquid chromatography Methods 0.000 description 1
RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 description 1
FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
238000000746 purification Methods 0.000 description 1
AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 1
125000000714 pyrimidinyl group Chemical group 0.000 description 1
125000001453 quaternary ammonium group Chemical group 0.000 description 1
150000003242 quaternary ammonium salts Chemical class 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical compound O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-UHFFFAOYSA-N 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
239000011343 solid material Substances 0.000 description 1
238000009331 sowing Methods 0.000 description 1
239000004455 soybean meal Substances 0.000 description 1
235000012424 soybean oil Nutrition 0.000 description 1
239000003549 soybean oil Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000010902 straw Substances 0.000 description 1
229960005322 streptomycin Drugs 0.000 description 1
QAHVHSLSRLSVGS-UHFFFAOYSA-N sulfamoyl chloride Chemical compound NS(Cl)(=O)=O QAHVHSLSRLSVGS-UHFFFAOYSA-N 0.000 description 1
HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
101150065184 sym-2 gene Proteins 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
150000003918 triazines Chemical class 0.000 description 1
125000003652 trifluoroethoxy group Chemical group FC(CO*)(F)F 0.000 description 1
230000005740 tumor formation Effects 0.000 description 1
229940054370 ultram Drugs 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 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
230000003612 virological effect Effects 0.000 description 1
238000005406 washing Methods 0.000 description 1
239000002023 wood Substances 0.000 description 1
239000010457 zeolite Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
- 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
- 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
- A01N55/00—Biocides, pest repellants or attractants, or plant growth regulators, containing organic compounds containing elements other than carbon, hydrogen, halogen, oxygen, nitrogen and sulfur
- 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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
- C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring
- C07F7/0814—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring said ring is substituted at a C ring atom by Si

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
Dentistry (AREA)
Wood Science & Technology (AREA)
Plant Pathology (AREA)
Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Agronomy & Crop Science (AREA)
General Health & Medical Sciences (AREA)
Pest Control & Pesticides (AREA)
Zoology (AREA)
Environmental Sciences (AREA)
Plural Heterocyclic Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)

SK1609-88A 1987-03-13 1988-03-11 Biocidal agent SK160988A3 (en)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
JP5845187		1987-03-13
JP8254687		1987-04-03
JP10657787		1987-04-30

Publications (2)

Publication Number	Publication Date
SK278722B6 SK278722B6 (sk)	1998-01-14
SK160988A3 true SK160988A3 (en)	1998-01-14

Family

ID=27296589

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK1609-88A SK160988A3 (en)	1987-03-13	1988-03-11	Biocidal agent

Country Status (29)

Country	Link
US (1)	US4995898A (fr)
EP (1)	EP0298196B1 (fr)
KR (1)	KR960002556B1 (fr)
CN (1)	CN1016309B (fr)
AR (1)	AR248013A1 (fr)
AT (1)	ATE90082T1 (fr)
AU (1)	AU601820B2 (fr)
BR (1)	BR8801098A (fr)
CA (1)	CA1339133C (fr)
CZ (1)	CZ283597B6 (fr)
DE (2)	DE298196T1 (fr)
DK (1)	DK171598B1 (fr)
ES (1)	ES2007318T3 (fr)
GR (1)	GR890300049T1 (fr)
HK (1)	HK1005448A1 (fr)
HU (1)	HU206245B (fr)
IL (1)	IL85662A (fr)
IN (1)	IN169974B (fr)
LU (1)	LU91198I2 (fr)
MX (1)	MX167182B (fr)
MY (1)	MY102741A (fr)
NL (1)	NL350005I2 (fr)
NO (1)	NO172435C (fr)
NZ (1)	NZ223793A (fr)
PH (1)	PH24476A (fr)
PL (1)	PL156434B1 (fr)
PT (1)	PT86974B (fr)
RO (2)	RO100213B1 (fr)
SK (1)	SK160988A3 (fr)

Families Citing this family (77)

* Cited by examiner, † Cited by third party
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US5045557A (en) *	1987-03-20	1991-09-03	Schering Agrochemicals Ltd.	Imidazable fungicides and use thereof
MY129863A (en) *	1988-03-11	2007-05-31	Ishihara Sangyo Kaisha	Biocidal composition
JPH02262562A (ja) *	1988-10-20	1990-10-25	Ishihara Sangyo Kaisha Ltd	イミダゾール系化合物
US5211737A (en) *	1989-01-31	1993-05-18	Basf Aktiengesellschaft	4-arryl-2-haloimidazole-5-carboxylic esters, the preparation and use thereof
GB8906965D0 (en) *	1989-03-28	1989-05-10	Schering Agrochemicals Ltd	Fungicides
US5223525A (en) *	1989-05-05	1993-06-29	Rhone-Poulenc Ag Company	Pesticidal 1-arylimidazoles
FR2653432A1 (fr) *	1989-10-20	1991-04-26	Rhone Poulenc Agrochimie	Herbicides derives de 2-azolyl nicotinate.
US5173503A (en) *	1989-11-15	1992-12-22	Schering Agrochemicals Limited	Imidazole fungicides
DE4004061A1 (de) *	1990-02-10	1991-08-14	Hoechst Ag	Neue imidazolverbindungen, verfahren zu deren herstellung, arzneimittel auf basis dieser verbindungen sowie einige zwischenprodukte
JPH0441481A (ja) *	1990-06-05	1992-02-12	Nippon Synthetic Chem Ind Co Ltd:The	イミダゾール類のハロゲン化方法
GB9023082D0 (en) *	1990-10-24	1990-12-05	Schering Agrochemicals Ltd	Fungicides
DE4139950A1 (de) *	1991-12-04	1993-06-09	Bayer Ag, 5090 Leverkusen, De	2-cyanobenzimidazole, ein verfahren zu ihrer herstellung und ihre verwendung und neue vorprodukte
DE69401486T2 (de) *	1993-11-12	1997-04-30	Ishihara Sangyo Kaisha	Verfahren zur Herstellung 2-cyanoimidazol Derivate
EP0765872B1 (fr)	1994-09-08	1999-12-01	Ishihara Sangyo Kaisha Ltd.	Procédé pour la préparation de 2-cyanoimidazoles 1-substitués
US6060604A (en) *	1995-03-31	2000-05-09	Florida State University	Pharmaceutical compounds comprising polyamines substituted with electron-affinic groups
US5700825A (en) *	1995-03-31	1997-12-23	Florida State University	Radiosensitizing diamines and their pharmaceutical preparations
DE19623207A1 (de) *	1996-06-11	1997-12-18	Bayer Ag	Imidazolderivate
UA67739C2 (uk) *	1997-04-25	2004-07-15	Ісіхара Сангіо Кайся Лтд.	Композиція та спосіб боротьби з шкідливими біоорганізмами
AU2002300275B2 (en) *	1997-04-25	2004-09-16	Ishihara Sangyo Kaisha, Ltd.	Composition for controlling harmful bio-organisms and method for controlling harmful bio-organisms using the same
JP4351789B2 (ja) *	1999-07-16	2009-10-28	石原産業株式会社	有害生物防除用組成物および有害生物の防除方法
EP1211245A4 (fr) *	1999-08-19	2002-10-30	Ishihara Sangyo Kaisha	Agents permettant de luter contre les maladies animales engendrees par des parasites
US6713500B2 (en)	1999-08-19	2004-03-30	Ishihara Sangyo Kaisha Ltd.	Agent for controlling animal diseases caused by parasites
ATE243933T1 (de) *	1999-12-13	2003-07-15	Bayer Cropscience Ag	Fungizide wirkstoffkombinationen
DE10019758A1 (de)	2000-04-20	2001-10-25	Bayer Ag	Fungizide Wirkstoffkombinationen
DE10103832A1 (de) *	2000-05-11	2001-11-15	Bayer Ag	Fungizide Wirkstoffkombinationen
DE10049804A1 (de) *	2000-10-09	2002-04-18	Bayer Ag	Wirkstoffkombinationen mit fungiziden und akariziden Eigenschaften
DE10063046A1 (de)	2000-12-18	2002-06-20	Basf Ag	Fungizide Mischungen
CA2431417A1 (fr) *	2000-12-18	2002-06-27	Basf Aktiengesellschaft	Melanges fongicides se basant sur des composes d'amide
MXPA03005634A (es) *	2001-01-16	2003-10-06	Basf Ag	Mezclas fungicidas.
BR0206440A (pt) *	2001-01-16	2003-12-30	Basf Ag	Misturas fungicidas, método para combater fungos nocivos, e, agente fungicida
IL156709A0 (en) *	2001-01-22	2004-01-04	Basf Ag	Fungicide mixtures
PL376887A1 (pl)	2002-11-15	2006-01-09	Basf Aktiengesellschaft	Mieszaniny grzybobójcze na bazie pochodnych imidazolu
DE10347090A1 (de)	2003-10-10	2005-05-04	Bayer Cropscience Ag	Synergistische fungizide Wirkstoffkombinationen
DE10349501A1 (de)	2003-10-23	2005-05-25	Bayer Cropscience Ag	Synergistische fungizide Wirkstoffkombinationen
WO2006009085A1 (fr)	2004-07-16	2006-01-26	Ishihara Sangyo Kaisha, Ltd.	Composition bactéricide pour utilisation agricole ou horticole et méthode de contrôle des maladies des plantes
DE102004049761A1 (de)	2004-10-12	2006-04-13	Bayer Cropscience Ag	Fungizide Wirkstoffkombinationen
DE102005015677A1 (de)	2005-04-06	2006-10-12	Bayer Cropscience Ag	Synergistische fungizide Wirkstoffkombinationen
MX2007015376A (es)	2005-06-09	2008-02-14	Bayer Cropscience Ag	Combinaciones de productos activos.
DE102005026482A1 (de)	2005-06-09	2006-12-14	Bayer Cropscience Ag	Wirkstoffkombinationen
EP1952689A4 (fr)	2005-11-22	2012-12-12	Ishihara Sangyo Kaisha	Composition germicide pour des applications agricoles et de jardinage et procede pour lutter contre des maladies des plantes
DE102006023263A1 (de) *	2006-05-18	2007-11-22	Bayer Cropscience Ag	Synergistische Wirkstoffkombinationen
EP2035018B1 (fr) *	2006-06-02	2014-10-22	Natural MA Inc.	Soufre microdimensioné pour la prevention et le traitement de maladies chez les humains et les animaux
DE102007045920B4 (de)	2007-09-26	2018-07-05	Bayer Intellectual Property Gmbh	Synergistische Wirkstoffkombinationen
JP5502354B2 (ja)	2008-03-28	2014-05-28	石原産業株式会社	農園芸用殺菌剤組成物及び植物病害の防除方法
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1988
- 1988-03-03 CA CA000560436A patent/CA1339133C/fr not_active Expired - Lifetime
- 1988-03-07 IN IN145/MAS/88A patent/IN169974B/en unknown
- 1988-03-08 NZ NZ223793A patent/NZ223793A/en unknown
- 1988-03-08 IL IL85662A patent/IL85662A/xx not_active IP Right Cessation
- 1988-03-09 PH PH36615A patent/PH24476A/en unknown
- 1988-03-09 MY MYPI88000239A patent/MY102741A/en unknown
- 1988-03-10 AU AU12883/88A patent/AU601820B2/en not_active Expired
- 1988-03-10 NO NO881066A patent/NO172435C/no not_active IP Right Cessation
- 1988-03-11 AR AR88310285A patent/AR248013A1/es active
- 1988-03-11 HU HU881180A patent/HU206245B/hu unknown
- 1988-03-11 BR BR8801098A patent/BR8801098A/pt not_active IP Right Cessation
- 1988-03-11 EP EP88103885A patent/EP0298196B1/fr not_active Expired - Lifetime
- 1988-03-11 DK DK133288A patent/DK171598B1/da not_active IP Right Cessation
- 1988-03-11 RO RO13256088A patent/RO100213B1/ro unknown
- 1988-03-11 ES ES88103885T patent/ES2007318T3/es not_active Expired - Lifetime
- 1988-03-11 CZ CS881609A patent/CZ283597B6/cs not_active IP Right Cessation
- 1988-03-11 RO RO141762A patent/RO104071B1/ro unknown
- 1988-03-11 DE DE198888103885T patent/DE298196T1/de active Pending
- 1988-03-11 SK SK1609-88A patent/SK160988A3/sk unknown
- 1988-03-11 AT AT88103885T patent/ATE90082T1/de active
- 1988-03-11 DE DE88103885T patent/DE3881443T2/de not_active Ceased
- 1988-03-11 MX MX010757A patent/MX167182B/es unknown
- 1988-03-11 PL PL1988271138A patent/PL156434B1/pl unknown
- 1988-03-12 KR KR1019880002618A patent/KR960002556B1/ko not_active IP Right Cessation
- 1988-03-12 CN CN88101228A patent/CN1016309B/zh not_active Expired
- 1988-03-14 PT PT86974A patent/PT86974B/pt not_active IP Right Cessation
- 1988-03-14 US US07/168,070 patent/US4995898A/en not_active Expired - Lifetime
1989
- 1989-05-25 GR GR89300049T patent/GR890300049T1/el unknown
1998
- 1998-05-26 HK HK98104540A patent/HK1005448A1/xx not_active IP Right Cessation
2002
- 2002-07-30 NL NL350005C patent/NL350005I2/nl unknown
2005
- 2005-09-23 LU LU91198C patent/LU91198I2/fr unknown

Also Published As

Publication number	Publication date
AU601820B2 (en)	1990-09-20
CZ160988A3 (cs)	1998-02-18
NO881066D0 (no)	1988-03-10
MY102741A (en)	1992-09-30
IN169974B (fr)	1992-01-18
DE298196T1 (de)	1989-05-11
DK133288A (da)	1988-09-14
NO172435B (no)	1993-04-13
PT86974A (pt)	1988-04-01
SK278722B6 (sk)	1998-01-14
PH24476A (en)	1990-07-18
AU1288388A (en)	1988-09-15
AR248013A1 (es)	1995-05-31
ES2007318T3 (es)	1994-11-01
GR890300049T1 (en)	1989-05-25
KR960002556B1 (ko)	1996-02-22
ES2007318A4 (es)	1989-06-16
HK1005448A1 (en)	1999-01-08
BR8801098A (pt)	1988-10-18
CN88101228A (zh)	1988-12-07
NL350005I2 (nl)	2002-11-01
EP0298196B1 (fr)	1993-06-02
HU206245B (en)	1992-10-28
LU91198I2 (fr)	2005-11-23
US4995898A (en)	1991-02-26
DE3881443D1 (de)	1993-07-08
CN1016309B (zh)	1992-04-22
MX167182B (es)	1993-03-09
CA1339133C (fr)	1997-07-29
DK171598B1 (da)	1997-02-17
ATE90082T1 (de)	1993-06-15
KR880011119A (ko)	1988-10-26
DK133288D0 (da)	1988-03-11
PL271138A1 (en)	1989-04-17
DE3881443T2 (de)	1993-11-25
RO100213B1 (en)	1992-11-20
NO172435C (no)	1993-07-21
NO881066L (no)	1988-09-14
RO104071B1 (en)	1993-04-15
NL350005I1 (nl)	2002-10-01
EP0298196A1 (fr)	1989-01-11
NZ223793A (en)	1990-12-21
CZ283597B6 (cs)	1998-05-13
IL85662A (en)	1993-02-21
IL85662A0 (en)	1988-08-31
HUT45844A (en)	1988-09-28
PT86974B (pt)	1992-06-30
PL156434B1 (en)	1992-03-31

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KR100744987B1 (ko)	2007-08-02	살진균제
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KR100349484B1 (ko)	2004-12-23	식물병해방제제
HU189678B (en)	1986-07-28	Fungicide and plant growth regulating compositions containing alkyl-azole derivatives as active substances
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CA2005155A1 (fr)	1990-06-13	Pyridazinones substituees, procedes de preparation et usages comme pesticides
JPH07258223A (ja)	1995-10-09	４−フェネチルアミノピリミジン誘導体、その製法及び農園芸用の有害生物防除剤
AU609846B2 (en)	1991-05-09	New thiazole compounds having fungicidal activity
US5814629A (en)	1998-09-29	Microbicides
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CA1340949C (fr)	2000-04-04	Composes d'imidazole et compositions biocides les comprenant, destinees a eliminer les organismes nusibles
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JPS6372678A (ja)	1988-04-02	イミダゾ−ル系化合物及び殺菌剤