CA1340949C - Composes d'imidazole et compositions biocides les comprenant, destinees a eliminer les organismes nusibles - Google Patents

Composes d'imidazole et compositions biocides les comprenant, destinees a eliminer les organismes nusibles

Info

Publication number: CA1340949C
Authority: CA; Canada
Prior art keywords: group; groups; phenyl; substituent; alkyl
Prior art date: 1987-03-13
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired - Lifetime

Application number

CA000617014A

Other languages

English (en)

Inventor

Rikuo Nasu

Terumasa Komyoji

Kazumi Suzuki

Toshio Nakajima

Takeshi Ohshima

Hideshi Yoshimura

Keiichiro Ito

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Ishihara Sangyo Kaisha Ltd

Original Assignee

Ishihara Sangyo Kaisha Ltd

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

1988-03-03

Publication date

2000-04-04

1987-04-30 Priority claimed from JP10655787A external-priority patent/JPS63275827A/ja

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

1988-03-03 Priority claimed from CA000560436A external-priority patent/CA1339133C/fr

2000-04-04 Application granted granted Critical

2000-04-04 Publication of CA1340949C publication Critical patent/CA1340949C/fr

2017-04-04 Anticipated expiration legal-status Critical

Status Expired - Lifetime legal-status Critical Current

Links

150000002460 imidazoles Chemical class 0.000 title abstract description 23
230000003115 biocidal effect Effects 0.000 title abstract description 7
239000000203 mixture Substances 0.000 title description 96
150000001875 compounds Chemical class 0.000 claims abstract description 194
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 127
125000005843 halogen group Chemical group 0.000 claims abstract description 90
-1 3,4-methylenedioxy groups Chemical group 0.000 claims abstract description 86
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 41
125000001424 substituent group Chemical group 0.000 claims abstract description 41
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 31
125000003545 alkoxy group Chemical group 0.000 claims abstract description 28
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 23
125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 21
125000004414 alkyl thio group Chemical group 0.000 claims abstract description 20
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 16
125000001544 thienyl group Chemical group 0.000 claims abstract description 13
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 12
125000004076 pyridyl group Chemical group 0.000 claims abstract description 12
125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 claims abstract description 9
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 9
125000004400 (C1-C12) alkyl group Chemical group 0.000 claims abstract description 8
125000002541 furyl group Chemical group 0.000 claims abstract description 8
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 5
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims abstract description 5
125000000882 C2-C6 alkenyl group Chemical group 0.000 claims abstract description 5
125000001624 naphthyl group Chemical group 0.000 claims abstract description 5
125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 claims abstract description 4
125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims abstract 18
125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims abstract 4
125000006374 C2-C10 alkenyl group Chemical group 0.000 claims abstract 4
125000005415 substituted alkoxy group Chemical group 0.000 claims abstract 2
125000000217 alkyl group Chemical group 0.000 claims description 35
125000001309 chloro group Chemical group Cl* 0.000 claims description 10
229910052801 chlorine Inorganic materials 0.000 claims description 8
125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 6
125000004860 4-ethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])C([H])([H])[H] 0.000 claims description 4
125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 4
239000000543 intermediate Substances 0.000 abstract description 21
229910052736 halogen Inorganic materials 0.000 abstract 1
150000002367 halogens Chemical class 0.000 abstract 1
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 97
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 85
238000002844 melting Methods 0.000 description 61
230000008018 melting Effects 0.000 description 61
239000002904 solvent Substances 0.000 description 58
238000012360 testing method Methods 0.000 description 57
238000006243 chemical reaction Methods 0.000 description 51
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 47
239000000243 solution Substances 0.000 description 46
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 40
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 37
239000011541 reaction mixture Substances 0.000 description 35
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 30
230000015572 biosynthetic process Effects 0.000 description 27
238000000034 method Methods 0.000 description 27
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 26
238000010898 silica gel chromatography Methods 0.000 description 26
238000003786 synthesis reaction Methods 0.000 description 25
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 24
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 23
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Substances C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 23
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 22
238000004821 distillation Methods 0.000 description 21
240000008067 Cucumis sativus Species 0.000 description 20
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 18
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 18
235000010799 Cucumis sativus var sativus Nutrition 0.000 description 17
238000009472 formulation Methods 0.000 description 16
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
238000011156 evaluation Methods 0.000 description 15
230000003902 lesion Effects 0.000 description 15
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 14
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 14
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 14
238000005406 washing Methods 0.000 description 14
241000233866 Fungi Species 0.000 description 13
239000004698 Polyethylene Substances 0.000 description 13
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 13
239000010410 layer Substances 0.000 description 13
238000010992 reflux Methods 0.000 description 13
240000007594 Oryza sativa Species 0.000 description 12
229920000573 polyethylene Polymers 0.000 description 12
229910000027 potassium carbonate Inorganic materials 0.000 description 12
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 11
229920003171 Poly (ethylene oxide) Polymers 0.000 description 11
239000000843 powder Substances 0.000 description 11
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 11
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 10
235000007688 Lycopersicon esculentum Nutrition 0.000 description 10
240000003768 Solanum lycopersicum Species 0.000 description 10
125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 10
125000003342 alkenyl group Chemical group 0.000 description 9
238000011081 inoculation Methods 0.000 description 9
239000002689 soil Substances 0.000 description 9
238000003756 stirring Methods 0.000 description 9
241000238631 Hexapoda Species 0.000 description 8
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
241000233679 Peronosporaceae Species 0.000 description 8
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 8
239000002253 acid Substances 0.000 description 8
239000003513 alkali Substances 0.000 description 8
239000000460 chlorine Substances 0.000 description 8
238000000605 extraction Methods 0.000 description 8
229910052757 nitrogen Inorganic materials 0.000 description 8
239000007921 spray Substances 0.000 description 8
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 7
241001454293 Tetranychus urticae Species 0.000 description 7
229960001701 chloroform Drugs 0.000 description 7
230000001276 controlling effect Effects 0.000 description 7
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 7
238000001035 drying Methods 0.000 description 7
JFCHSQDLLFJHOA-UHFFFAOYSA-N n,n-dimethylsulfamoyl chloride Chemical compound CN(C)S(Cl)(=O)=O JFCHSQDLLFJHOA-UHFFFAOYSA-N 0.000 description 7
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 7
230000003449 preventive effect Effects 0.000 description 7
239000011734 sodium Substances 0.000 description 7
239000000725 suspension Substances 0.000 description 7
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 6
239000005995 Aluminium silicate Substances 0.000 description 6
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 6
WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 6
JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
125000002877 alkyl aryl group Chemical group 0.000 description 6
235000012211 aluminium silicate Nutrition 0.000 description 6
ANUZKYYBDVLEEI-UHFFFAOYSA-N butane;hexane;lithium Chemical compound [Li]CCCC.CCCCCC ANUZKYYBDVLEEI-UHFFFAOYSA-N 0.000 description 6
239000003795 chemical substances by application Substances 0.000 description 6
230000000694 effects Effects 0.000 description 6
125000002883 imidazolyl group Chemical group 0.000 description 6
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 6
DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 description 6
229910052708 sodium Inorganic materials 0.000 description 6
239000007787 solid Substances 0.000 description 6
241000238876 Acari Species 0.000 description 5
244000075850 Avena orientalis Species 0.000 description 5
235000007319 Avena orientalis Nutrition 0.000 description 5
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 5
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 5
ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 5
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 5
235000007164 Oryza sativa Nutrition 0.000 description 5
244000046052 Phaseolus vulgaris Species 0.000 description 5
239000002671 adjuvant Substances 0.000 description 5
150000008064 anhydrides Chemical class 0.000 description 5
VTYYLEPIZMXCLO-UHFFFAOYSA-L calcium carbonate Substances [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 5
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 5
239000000969 carrier Substances 0.000 description 5
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 5
238000001914 filtration Methods 0.000 description 5
230000028644 hyphal growth Effects 0.000 description 5
230000005764 inhibitory process Effects 0.000 description 5
125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 5
235000009566 rice Nutrition 0.000 description 5
125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 4
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-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
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
241000721621 Myzus persicae Species 0.000 description 4
235000011114 ammonium hydroxide Nutrition 0.000 description 4
RBHJBMIOOPYDBQ-UHFFFAOYSA-N carbon dioxide;propan-2-one Chemical compound O=C=O.CC(C)=O RBHJBMIOOPYDBQ-UHFFFAOYSA-N 0.000 description 4
238000001816 cooling Methods 0.000 description 4
239000013078 crystal Substances 0.000 description 4
235000019441 ethanol Nutrition 0.000 description 4
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
239000000417 fungicide Substances 0.000 description 4
150000002500 ions Chemical class 0.000 description 4
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 4
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 4
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 4
229910000069 nitrogen hydride Inorganic materials 0.000 description 4
231100000194 ovacidal Toxicity 0.000 description 4
230000003151 ovacidal effect Effects 0.000 description 4
239000000377 silicon dioxide Substances 0.000 description 4
239000000126 substance Substances 0.000 description 4
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
WPWHSFAFEBZWBB-UHFFFAOYSA-N 1-butyl radical Chemical compound [CH2]CCC WPWHSFAFEBZWBB-UHFFFAOYSA-N 0.000 description 3
HNEGJTWNOOWEMH-UHFFFAOYSA-N 1-fluoropropane Chemical group [CH2]CCF HNEGJTWNOOWEMH-UHFFFAOYSA-N 0.000 description 3
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 3
IIVWHGMLFGNMOW-UHFFFAOYSA-N 2-methylpropane Chemical compound C[C](C)C IIVWHGMLFGNMOW-UHFFFAOYSA-N 0.000 description 3
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 3
125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 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
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
240000002791 Brassica napus Species 0.000 description 3
235000011293 Brassica napus Nutrition 0.000 description 3
235000000540 Brassica rapa subsp rapa Nutrition 0.000 description 3
RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 3
239000005909 Kieselgur Substances 0.000 description 3
241001470017 Laodelphax striatella Species 0.000 description 3
229910017974 NH40H Inorganic materials 0.000 description 3
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
229910019142 PO4 Inorganic materials 0.000 description 3
241000233622 Phytophthora infestans Species 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 3
229910052783 alkali metal Inorganic materials 0.000 description 3
150000001340 alkali metals Chemical class 0.000 description 3
238000004458 analytical method Methods 0.000 description 3
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
229910000019 calcium carbonate Inorganic materials 0.000 description 3
238000004440 column chromatography Methods 0.000 description 3
235000014113 dietary fatty acids Nutrition 0.000 description 3
201000010099 disease Diseases 0.000 description 3
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 3
YDEXUEFDPVHGHE-GGMCWBHBSA-L disodium;(2r)-3-(2-hydroxy-3-methoxyphenyl)-2-[2-methoxy-4-(3-sulfonatopropyl)phenoxy]propane-1-sulfonate Chemical compound [Na+].[Na+].COC1=CC=CC(C[C@H](CS([O-])(=O)=O)OC=2C(=CC(CCCS([O-])(=O)=O)=CC=2)OC)=C1O YDEXUEFDPVHGHE-GGMCWBHBSA-L 0.000 description 3
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239000000194 fatty acid Substances 0.000 description 3
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125000002350 geranyl group Chemical group [H]C([*])([H])/C([H])=C(C([H])([H])[H])/C([H])([H])C([H])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
229910000037 hydrogen sulfide Inorganic materials 0.000 description 3
239000005457 ice water Substances 0.000 description 3
239000002917 insecticide Substances 0.000 description 3
JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 3
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 3
238000002955 isolation Methods 0.000 description 3
239000002609 medium Substances 0.000 description 3
125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 3
PVWOIHVRPOBWPI-UHFFFAOYSA-N n-propyl iodide Chemical compound CCCI PVWOIHVRPOBWPI-UHFFFAOYSA-N 0.000 description 3
239000003921 oil Substances 0.000 description 3
235000019198 oils Nutrition 0.000 description 3
239000010452 phosphate Substances 0.000 description 3
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 3
238000000746 purification Methods 0.000 description 3
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 3
239000008096 xylene Substances 0.000 description 3
FYGHSUNMUKGBRK-UHFFFAOYSA-N 1,2,3-trimethylbenzene Chemical compound CC1=CC=CC(C)=C1C FYGHSUNMUKGBRK-UHFFFAOYSA-N 0.000 description 2
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 2
125000004847 2-fluorobenzyl group Chemical group [H]C1=C([H])C(F)=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 description 2
125000006179 2-methyl benzyl group Chemical group [H]C1=C([H])C(=C(C([H])=C1[H])C([H])([H])*)C([H])([H])[H] 0.000 description 2
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239000003139 biocide Substances 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
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239000011575 calcium Substances 0.000 description 1
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238000004587 chromatography analysis Methods 0.000 description 1
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239000004927 clay Substances 0.000 description 1
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239000012043 crude product Substances 0.000 description 1
125000004122 cyclic group Chemical group 0.000 description 1
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238000000354 decomposition reaction Methods 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
UOAMTSKGCBMZTC-UHFFFAOYSA-N dicofol Chemical compound C=1C=C(Cl)C=CC=1C(C(Cl)(Cl)Cl)(O)C1=CC=C(Cl)C=C1 UOAMTSKGCBMZTC-UHFFFAOYSA-N 0.000 description 1
238000007865 diluting Methods 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 description 1
SDIXRDNYIMOKSG-UHFFFAOYSA-L disodium methyl arsenate Chemical compound [Na+].[Na+].C[As]([O-])([O-])=O SDIXRDNYIMOKSG-UHFFFAOYSA-L 0.000 description 1
150000004659 dithiocarbamates Chemical class 0.000 description 1
238000003411 electrode reaction Methods 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
238000003818 flash chromatography Methods 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
125000001153 fluoro group Chemical group F* 0.000 description 1
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150000008282 halocarbons Chemical class 0.000 description 1
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150000002373 hemiacetals Chemical class 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
125000005842 heteroatom Chemical group 0.000 description 1
UQWQCMSYGMAGKF-UHFFFAOYSA-N hexane;lithium Chemical compound [Li].CCCCCC UQWQCMSYGMAGKF-UHFFFAOYSA-N 0.000 description 1
230000003054 hormonal effect Effects 0.000 description 1
DKAGJZJALZXOOV-UHFFFAOYSA-N hydrate;hydrochloride Chemical compound O.Cl DKAGJZJALZXOOV-UHFFFAOYSA-N 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
ATADHKWKHYVBTJ-UHFFFAOYSA-N hydron;4-[1-hydroxy-2-(methylamino)ethyl]benzene-1,2-diol;chloride Chemical compound Cl.CNCC(O)C1=CC=C(O)C(O)=C1 ATADHKWKHYVBTJ-UHFFFAOYSA-N 0.000 description 1
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
125000006289 hydroxybenzyl group Chemical group 0.000 description 1
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235000015250 liver sausages Nutrition 0.000 description 1
150000002736 metal compounds Chemical class 0.000 description 1
FFEARJCKVFRZRR-UHFFFAOYSA-N methionine Chemical compound CSCCC(N)C(O)=O FFEARJCKVFRZRR-UHFFFAOYSA-N 0.000 description 1
125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
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210000004080 milk Anatomy 0.000 description 1
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230000003129 miticidal effect Effects 0.000 description 1
238000012986 modification Methods 0.000 description 1
230000004048 modification Effects 0.000 description 1
150000002780 morpholines Chemical class 0.000 description 1
UJQMLHKSZKBMMO-UHFFFAOYSA-N n,n-diethylethanamine;pyridine Chemical compound C1=CC=NC=C1.CCN(CC)CC UJQMLHKSZKBMMO-UHFFFAOYSA-N 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
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000004433 nitrogen atom Chemical group N* 0.000 description 1
GSGDTSDELPUTKU-UHFFFAOYSA-N nonoxybenzene Chemical compound CCCCCCCCCOC1=CC=CC=C1 GSGDTSDELPUTKU-UHFFFAOYSA-N 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
238000010899 nucleation Methods 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
239000012044 organic layer Substances 0.000 description 1
150000002898 organic sulfur compounds Chemical class 0.000 description 1
150000002903 organophosphorus compounds Chemical class 0.000 description 1
230000001717 pathogenic effect Effects 0.000 description 1
239000000575 pesticide Substances 0.000 description 1
239000003444 phase transfer catalyst Substances 0.000 description 1
229910052698 phosphorus Inorganic materials 0.000 description 1
239000011574 phosphorus Substances 0.000 description 1
230000003032 phytopathogenic effect Effects 0.000 description 1
150000004885 piperazines Chemical class 0.000 description 1
125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
125000003386 piperidinyl group Chemical group 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
ZNNZYHKDIALBAK-UHFFFAOYSA-M potassium thiocyanate Chemical compound [K+].[S-]C#N ZNNZYHKDIALBAK-UHFFFAOYSA-M 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
238000002953 preparative HPLC Methods 0.000 description 1
230000002035 prolonged effect Effects 0.000 description 1
DRINJBFRTLBHNF-UHFFFAOYSA-N propane-2-sulfonyl chloride Chemical compound CC(C)S(Cl)(=O)=O DRINJBFRTLBHNF-UHFFFAOYSA-N 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
238000004080 punching Methods 0.000 description 1
239000002728 pyrethroid Chemical class 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
125000000719 pyrrolidinyl 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
150000003252 quinoxalines Chemical class 0.000 description 1
238000011160 research Methods 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
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
MNWBNISUBARLIT-UHFFFAOYSA-N sodium cyanide Chemical compound [Na+].N#[C-] MNWBNISUBARLIT-UHFFFAOYSA-N 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
HLPHHOLZSKWDAK-UHFFFAOYSA-M sodium;formaldehyde;naphthalene-1-sulfonate Chemical compound [Na+].O=C.C1=CC=C2C(S(=O)(=O)[O-])=CC=CC2=C1 HLPHHOLZSKWDAK-UHFFFAOYSA-M 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
239000008107 starch Substances 0.000 description 1
239000010902 straw Substances 0.000 description 1
229960005322 streptomycin Drugs 0.000 description 1
150000003450 sulfenic acids Chemical class 0.000 description 1
150000003462 sulfoxides Chemical class 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
230000002194 synthesizing effect Effects 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
150000003555 thioacetals Chemical class 0.000 description 1
VPAYJEUHKVESSD-UHFFFAOYSA-N trifluoroiodomethane Chemical compound FC(F)(F)I VPAYJEUHKVESSD-UHFFFAOYSA-N 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
235000013311 vegetables Nutrition 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
239000002023 wood Substances 0.000 description 1

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Plural Heterocyclic Compounds (AREA)

CA000617014A 1987-03-13 1988-03-03 Composes d'imidazole et compositions biocides les comprenant, destinees a eliminer les organismes nusibles Expired - Lifetime CA1340949C (fr)

Applications Claiming Priority (7)

Application Number	Priority Date	Filing Date	Title
JP5845187		1987-03-13
JP58451/87		1987-03-13
JP8254687		1987-04-03
JP82546/87		1987-04-03
JP10655787A JPS63275827A (ja)	1987-04-30	1987-04-30	流体封入式マウント装置を用いた防振方法
JP106557/87		1987-04-30
CA000560436A CA1339133C (fr)	1987-03-13	1988-03-03	Derives de l'imidazole et compositions a base de ces derives pour l'elimination d'organismes nuisibles

Related Parent Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000560436A Division CA1339133C (fr)	1987-03-13	1988-03-03	Derives de l'imidazole et compositions a base de ces derives pour l'elimination d'organismes nuisibles

Publications (1)

Publication Number	Publication Date
CA1340949C true CA1340949C (fr)	2000-04-04

Family

ID=33425259

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000617014A Expired - Lifetime CA1340949C (fr)	1987-03-13	1988-03-03	Composes d'imidazole et compositions biocides les comprenant, destinees a eliminer les organismes nusibles

Country Status (1)

Country	Link
CA (1)	CA1340949C (fr)

1988
- 1988-03-03 CA CA000617014A patent/CA1340949C/fr not_active Expired - Lifetime

Publication	Publication Date	Title
CA1339133C (fr)	1997-07-29	Derives de l'imidazole et compositions a base de ces derives pour l'elimination d'organismes nuisibles
HK1005448B (en)	1999-01-08	Imidazole compounds and blocidal compositions comprising the same
EP0665225B1 (fr)	1996-11-27	4-Phénylaminopyrimidines, procédé pour leur préparation et pesticides pour l'agriculture et l'horticulture les contenant
US5389651A (en)	1995-02-14	Nitrogen-containing heterocyclyl-oxy and -thio compounds useful as pesticides
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CA1340949C (fr)	2000-04-04	Composes d'imidazole et compositions biocides les comprenant, destinees a eliminer les organismes nusibles
US4808210A (en)	1989-02-28	Herbicidal method of using 5-pyrazolones
JPH06157469A (ja)	1994-06-03	ピラゾールカルボニルウレア誘導体、その製法及び有害生物防除剤
JPH10287659A (ja)	1998-10-27	１，２，３−チアジアゾール化合物、その製法及び農園芸用の有害生物防除剤
PH26182A (en)	1992-03-18	Intermediate compounds for biocidal imidazole compounds
JP2666100B2 (ja)	1997-10-22	２−アシルアミノ−２−チアゾリン化合物、その製法及び有害生物防除剤
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JP3083032B2 (ja)	2000-09-04	４−アミノピリミジン誘導体、その製法及び有害生物防除剤
JP2673848B2 (ja)	1997-11-05	アルキルアミノピリミジン誘導体、その製法及び有害生物防除剤
RU2014326C1 (ru)	1994-06-15	Производные имидазола
JP2666099B2 (ja)	1997-10-22	２−アシルアミノ−２−チアゾリン化合物、その製法及び有害生物防除剤
US20040063945A1 (en)	2004-04-01	6-(1-fluoroethyl)-5-iodo-4-aminopyrimidine compounds process for preparation of the same and pest controllers for agricultural and horticultural use
JP3485123B2 (ja)	2004-01-13	フェノキシアルキルアミン誘導体、その製法及び農園芸用の有害生物防除剤
EP1074546A1 (fr)	2001-02-07	Derives 5-iodo-4-phenethylaminopyrimidine, leurs intermediaires, procede de production associe, et pesticides agricoles et horticoles
JPH08269021A (ja)	1996-10-15	４−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
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