JP2000515135A - 置換されたｎ―（５―イソチアゾリル）チオアミド類 - Google Patents

置換されたｎ―（５―イソチアゾリル）チオアミド類

Info

Publication number: JP2000515135A
Authority: JP; Japan
Prior art keywords: alkyl; fluorine; atoms; chlorine; different
Prior art date: 1996-07-16
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Pending

Application number

JP10505570A

Other languages

English (en)

Japanese (ja)

Inventor

ハイル，マルクス

ブレチユナイダー，トマス

クレーフエルト，ゲルト

エルデレン，クリストフ

トウルベルク，アンドレアス

メンケ，ノルベルト

Original Assignee

バイエル・アクチエンゲゼルシヤフト

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.)

1996-07-16

Filing date

1997-07-03

Publication date

2000-11-14

1997-07-03 Application filed by バイエル・アクチエンゲゼルシヤフト filed Critical バイエル・アクチエンゲゼルシヤフト

2000-11-14 Publication of JP2000515135A publication Critical patent/JP2000515135A/ja

Status Pending legal-status Critical Current

Links

238000000034 method Methods 0.000 claims abstract description 34
241000607479 Yersinia pestis Species 0.000 claims abstract description 12
-1 cyano, nitro, thiocyanato Chemical group 0.000 claims description 91
150000001875 compounds Chemical class 0.000 claims description 73
229910052731 fluorine Inorganic materials 0.000 claims description 67
YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical group [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims description 66
239000000460 chlorine Chemical group 0.000 claims description 66
239000011737 fluorine Substances 0.000 claims description 66
229910052801 chlorine Inorganic materials 0.000 claims description 59
125000005843 halogen group Chemical group 0.000 claims description 56
125000001424 substituent group Chemical group 0.000 claims description 31
229910052736 halogen Inorganic materials 0.000 claims description 28
150000002367 halogens Chemical class 0.000 claims description 28
229910052739 hydrogen Inorganic materials 0.000 claims description 19
239000001257 hydrogen Substances 0.000 claims description 19
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 16
125000000217 alkyl group Chemical group 0.000 claims description 15
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 14
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 14
239000003795 chemical substances by application Substances 0.000 claims description 13
239000003085 diluting agent Substances 0.000 claims description 13
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 13
125000001309 chloro group Chemical group Cl* 0.000 claims description 12
125000004093 cyano group Chemical group *C#N 0.000 claims description 12
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 11
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 11
229910052794 bromium Chemical group 0.000 claims description 11
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 10
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 10
125000004414 alkyl thio group Chemical group 0.000 claims description 8
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 7
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 7
125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 6
125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 6
125000002947 alkylene group Chemical group 0.000 claims description 5
239000002585 base Substances 0.000 claims description 5
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 5
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 5
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 5
239000012988 Dithioester Substances 0.000 claims description 4
150000001340 alkali metals Chemical class 0.000 claims description 4
125000004183 alkoxy alkyl group Chemical group 0.000 claims description 4
125000003545 alkoxy group Chemical group 0.000 claims description 4
125000004429 atom Chemical group 0.000 claims description 4
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 4
125000005022 dithioester group Chemical group 0.000 claims description 4
125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 4
125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 claims description 4
125000001188 haloalkyl group Chemical group 0.000 claims description 4
238000004519 manufacturing process Methods 0.000 claims description 4
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 4
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 4
125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 4
229910052783 alkali metal Inorganic materials 0.000 claims description 3
125000000753 cycloalkyl group Chemical group 0.000 claims description 3
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 3
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 3
125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 3
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 2
125000004450 alkenylene group Chemical group 0.000 claims description 2
125000005092 alkenyloxycarbonyl group Chemical group 0.000 claims description 2
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
125000006350 alkyl thio alkyl group Chemical group 0.000 claims description 2
125000003710 aryl alkyl group Chemical group 0.000 claims description 2
125000004391 aryl sulfonyl group Chemical group 0.000 claims description 2
125000000392 cycloalkenyl group Chemical group 0.000 claims description 2
125000004672 ethylcarbonyl group Chemical group [H]C([H])([H])C([H])([H])C(*)=O 0.000 claims description 2
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
125000004674 methylcarbonyl group Chemical group CC(=O)* 0.000 claims description 2
125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 2
125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 2
125000003107 substituted aryl group Chemical group 0.000 claims description 2
239000004094 surface-active agent Substances 0.000 claims description 2
125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 claims description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 29
125000004435 hydrogen atom Chemical class [H]* 0.000 claims 8
230000000361 pesticidal effect Effects 0.000 claims 2
125000004642 (C1-C12) alkoxy group Chemical group 0.000 claims 1
125000003161 (C1-C6) alkylene group Chemical group 0.000 claims 1
241001024304 Mino Species 0.000 claims 1
241001553014 Myrsine salicina Species 0.000 claims 1
125000005529 alkyleneoxy group Chemical group 0.000 claims 1
239000000575 pesticide Substances 0.000 claims 1
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
241001465754 Metazoa Species 0.000 abstract description 9
238000002360 preparation method Methods 0.000 abstract description 6
150000003556 thioamides Chemical class 0.000 abstract 1
241000894007 species Species 0.000 description 58
239000000203 mixture Substances 0.000 description 31
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 30
239000002904 solvent Substances 0.000 description 21
239000000126 substance Substances 0.000 description 19
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
238000009472 formulation Methods 0.000 description 15
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
241000238876 Acari Species 0.000 description 11
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
239000000417 fungicide Substances 0.000 description 9
239000003921 oil Substances 0.000 description 9
235000019198 oils Nutrition 0.000 description 9
241000254173 Coleoptera Species 0.000 description 8
241000238631 Hexapoda Species 0.000 description 8
239000002917 insecticide Substances 0.000 description 8
239000000047 product Substances 0.000 description 8
239000011877 solvent mixture Substances 0.000 description 8
241000255925 Diptera Species 0.000 description 7
239000011230 binding agent Substances 0.000 description 7
238000009835 boiling Methods 0.000 description 7
238000006243 chemical reaction Methods 0.000 description 7
239000003995 emulsifying agent Substances 0.000 description 7
239000000463 material Substances 0.000 description 7
239000000843 powder Substances 0.000 description 7
239000002023 wood Substances 0.000 description 7
150000001338 aliphatic hydrocarbons Chemical class 0.000 description 6
239000012141 concentrate Substances 0.000 description 6
235000008504 concentrate Nutrition 0.000 description 6
239000008187 granular material Substances 0.000 description 6
GKZNVLJEHYUFIC-UHFFFAOYSA-N 1,2-thiazol-5-amine Chemical class NC1=CC=NS1 GKZNVLJEHYUFIC-UHFFFAOYSA-N 0.000 description 5
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 5
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
229920000180 alkyd Polymers 0.000 description 5
239000000839 emulsion Substances 0.000 description 5
239000002480 mineral oil Substances 0.000 description 5
VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
239000007858 starting material Substances 0.000 description 5
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 4
241000196324 Embryophyta Species 0.000 description 4
241000258937 Hemiptera Species 0.000 description 4
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 4
241001674048 Phthiraptera Species 0.000 description 4
241001414989 Thysanoptera Species 0.000 description 4
FPIPGXGPPPQFEQ-OVSJKPMPSA-N all-trans-retinol Chemical compound OC\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-OVSJKPMPSA-N 0.000 description 4
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
239000010949 copper Substances 0.000 description 4
229910052802 copper Inorganic materials 0.000 description 4
229960001591 cyfluthrin Drugs 0.000 description 4
QQODLKZGRKWIFG-QSFXBCCZSA-N cyfluthrin Chemical compound CC1(C)[C@@H](C=C(Cl)Cl)[C@H]1C(=O)O[C@@H](C#N)C1=CC=C(F)C(OC=2C=CC=CC=2)=C1 QQODLKZGRKWIFG-QSFXBCCZSA-N 0.000 description 4
230000000694 effects Effects 0.000 description 4
150000002148 esters Chemical class 0.000 description 4
150000002170 ethers Chemical class 0.000 description 4
230000000855 fungicidal effect Effects 0.000 description 4
229910052500 inorganic mineral Inorganic materials 0.000 description 4
LCCNCVORNKJIRZ-UHFFFAOYSA-N parathion Chemical compound CCOP(=S)(OCC)OC1=CC=C([N+]([O-])=O)C=C1 LCCNCVORNKJIRZ-UHFFFAOYSA-N 0.000 description 4
238000012545 processing Methods 0.000 description 4
229920005989 resin Polymers 0.000 description 4
239000011347 resin Substances 0.000 description 4
239000007787 solid Substances 0.000 description 4
XLNZEKHULJKQBA-UHFFFAOYSA-N terbufos Chemical compound CCOP(=S)(OCC)SCSC(C)(C)C XLNZEKHULJKQBA-UHFFFAOYSA-N 0.000 description 4
STMIIPIFODONDC-UHFFFAOYSA-N 2-(2,4-dichlorophenyl)-1-(1H-1,2,4-triazol-1-yl)hexan-2-ol Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(O)(CCCC)CN1C=NC=N1 STMIIPIFODONDC-UHFFFAOYSA-N 0.000 description 3
UFNOUKDBUJZYDE-UHFFFAOYSA-N 2-(4-chlorophenyl)-3-cyclopropyl-1-(1H-1,2,4-triazol-1-yl)butan-2-ol Chemical compound C1=NC=NN1CC(O)(C=1C=CC(Cl)=CC=1)C(C)C1CC1 UFNOUKDBUJZYDE-UHFFFAOYSA-N 0.000 description 3
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
BQMRHYBXRAYYQS-UHFFFAOYSA-N 4-dihydroxyphosphinothioyloxy-n,n-diethyl-6-methylpyrimidin-2-amine Chemical compound CCN(CC)C1=NC(C)=CC(OP(O)(O)=S)=N1 BQMRHYBXRAYYQS-UHFFFAOYSA-N 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
241001124076 Aphididae Species 0.000 description 3
241000238659 Blatta Species 0.000 description 3
241000256054 Culex <genus> Species 0.000 description 3
241000254171 Curculionidae Species 0.000 description 3
239000005946 Cypermethrin Substances 0.000 description 3
239000005757 Cyproconazole Substances 0.000 description 3
MDNWOSOZYLHTCG-UHFFFAOYSA-N Dichlorophen Chemical compound OC1=CC=C(Cl)C=C1CC1=CC(Cl)=CC=C1O MDNWOSOZYLHTCG-UHFFFAOYSA-N 0.000 description 3
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241001660203 Gasterophilus Species 0.000 description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 3
241000256602 Isoptera Species 0.000 description 3
241000255777 Lepidoptera Species 0.000 description 3
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239000005868 Metconazole Substances 0.000 description 3
240000001307 Myosotis scorpioides Species 0.000 description 3
241000244206 Nematoda Species 0.000 description 3
229910019142 PO4 Inorganic materials 0.000 description 3
241000238675 Periplaneta americana Species 0.000 description 3
239000005822 Propiconazole Substances 0.000 description 3
241001481703 Rhipicephalus <genus> Species 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 3
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ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
150000004945 aromatic hydrocarbons Chemical class 0.000 description 3
AKNQMEBLVAMSNZ-UHFFFAOYSA-N azaconazole Chemical compound ClC1=CC(Cl)=CC=C1C1(CN2N=CN=C2)OCCO1 AKNQMEBLVAMSNZ-UHFFFAOYSA-N 0.000 description 3
229950000294 azaconazole Drugs 0.000 description 3
KAATUXNTWXVJKI-UHFFFAOYSA-N cypermethrin Chemical compound CC1(C)C(C=C(Cl)Cl)C1C(=O)OC(C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 KAATUXNTWXVJKI-UHFFFAOYSA-N 0.000 description 3
229960005424 cypermethrin Drugs 0.000 description 3
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UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
239000002270 dispersing agent Substances 0.000 description 3
239000000975 dye Substances 0.000 description 3
238000001704 evaporation Methods 0.000 description 3
230000008020 evaporation Effects 0.000 description 3
NYPJDWWKZLNGGM-UHFFFAOYSA-N fenvalerate Aalpha Natural products C=1C=C(Cl)C=CC=1C(C(C)C)C(=O)OC(C#N)C(C=1)=CC=CC=1OC1=CC=CC=C1 NYPJDWWKZLNGGM-UHFFFAOYSA-N 0.000 description 3
125000001475 halogen functional group Chemical group 0.000 description 3
239000007788 liquid Substances 0.000 description 3
229910052751 metal Inorganic materials 0.000 description 3
239000002184 metal Substances 0.000 description 3
XWPZUHJBOLQNMN-UHFFFAOYSA-N metconazole Chemical compound C1=NC=NN1CC1(O)C(C)(C)CCC1CC1=CC=C(Cl)C=C1 XWPZUHJBOLQNMN-UHFFFAOYSA-N 0.000 description 3
238000002156 mixing Methods 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
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239000003208 petroleum Substances 0.000 description 3
235000021317 phosphate Nutrition 0.000 description 3
WHHIPMZEDGBUCC-UHFFFAOYSA-N probenazole Chemical compound C1=CC=C2C(OCC=C)=NS(=O)(=O)C2=C1 WHHIPMZEDGBUCC-UHFFFAOYSA-N 0.000 description 3
STJLVHWMYQXCPB-UHFFFAOYSA-N propiconazole Chemical compound O1C(CCC)COC1(C=1C(=CC(Cl)=CC=1)Cl)CN1N=CN=C1 STJLVHWMYQXCPB-UHFFFAOYSA-N 0.000 description 3
150000003839 salts Chemical class 0.000 description 3
239000000243 solution Substances 0.000 description 3
229910052717 sulfur Inorganic materials 0.000 description 3
239000011593 sulfur Substances 0.000 description 3
239000000725 suspension Substances 0.000 description 3
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238000012360 testing method Methods 0.000 description 3
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235000015112 vegetable and seed oil Nutrition 0.000 description 3
239000008158 vegetable oil Substances 0.000 description 3
KAATUXNTWXVJKI-NSHGMRRFSA-N (1R)-cis-(alphaS)-cypermethrin Chemical compound CC1(C)[C@@H](C=C(Cl)Cl)[C@H]1C(=O)O[C@H](C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 KAATUXNTWXVJKI-NSHGMRRFSA-N 0.000 description 2
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FSJYRLHKLVGCNH-UHFFFAOYSA-N (3-tert-butylphenyl) n-methylcarbamate Chemical compound CNC(=O)OC1=CC=CC(C(C)(C)C)=C1 FSJYRLHKLVGCNH-UHFFFAOYSA-N 0.000 description 2
VEMKTZHHVJILDY-WOJBJXKFSA-N (5-benzylfuran-3-yl)methyl (1s,3r)-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropane-1-carboxylate Chemical compound CC1(C)[C@H](C=C(C)C)[C@@H]1C(=O)OCC1=COC(CC=2C=CC=CC=2)=C1 VEMKTZHHVJILDY-WOJBJXKFSA-N 0.000 description 2
125000004400 (C1-C12) alkyl group Chemical group 0.000 description 2
SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 2
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VGPIBGGRCVEHQZ-UHFFFAOYSA-N 1-(biphenyl-4-yloxy)-3,3-dimethyl-1-(1,2,4-triazol-1-yl)butan-2-ol Chemical compound C1=NC=NN1C(C(O)C(C)(C)C)OC(C=C1)=CC=C1C1=CC=CC=C1 VGPIBGGRCVEHQZ-UHFFFAOYSA-N 0.000 description 2
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IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 description 2
JTPNRXUCIXHOKM-UHFFFAOYSA-N 1-chloronaphthalene Chemical compound C1=CC=C2C(Cl)=CC=CC2=C1 JTPNRXUCIXHOKM-UHFFFAOYSA-N 0.000 description 2
NFDXQGNDWIPXQL-UHFFFAOYSA-N 1-cyclooctyldiazocane Chemical compound C1CCCCCCC1N1NCCCCCC1 NFDXQGNDWIPXQL-UHFFFAOYSA-N 0.000 description 2
YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Chemical compound C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 2
YTOPFCCWCSOHFV-UHFFFAOYSA-N 2,6-dimethyl-4-tridecylmorpholine Chemical compound CCCCCCCCCCCCCN1CC(C)OC(C)C1 YTOPFCCWCSOHFV-UHFFFAOYSA-N 0.000 description 2
GQWWGRUJOCIUKI-UHFFFAOYSA-N 2-[3-(2-methyl-1-oxopyrrolo[1,2-a]pyrazin-3-yl)propyl]guanidine Chemical compound O=C1N(C)C(CCCN=C(N)N)=CN2C=CC=C21 GQWWGRUJOCIUKI-UHFFFAOYSA-N 0.000 description 2
WNZQDUSMALZDQF-UHFFFAOYSA-N 2-benzofuran-1(3H)-one Chemical compound C1=CC=C2C(=O)OCC2=C1 WNZQDUSMALZDQF-UHFFFAOYSA-N 0.000 description 2
WADSJYLPJPTMLN-UHFFFAOYSA-N 3-(cycloundecen-1-yl)-1,2-diazacycloundec-2-ene Chemical compound C1CCCCCCCCC=C1C1=NNCCCCCCCC1 WADSJYLPJPTMLN-UHFFFAOYSA-N 0.000 description 2
239000005660 Abamectin Substances 0.000 description 2
241000934064 Acarus siro Species 0.000 description 2
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241000902874 Agelastica alni Species 0.000 description 2
239000005877 Alpha-Cypermethrin Substances 0.000 description 2
241000238679 Amblyomma Species 0.000 description 2
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QYPNKSZPJQQLRK-UHFFFAOYSA-N tebufenozide Chemical compound C1=CC(CC)=CC=C1C(=O)NN(C(C)(C)C)C(=O)C1=CC(C)=CC(C)=C1 QYPNKSZPJQQLRK-UHFFFAOYSA-N 0.000 description 1
AWYOMXWDGWUJHS-UHFFFAOYSA-N tebupirimfos Chemical compound CCOP(=S)(OC(C)C)OC1=CN=C(C(C)(C)C)N=C1 AWYOMXWDGWUJHS-UHFFFAOYSA-N 0.000 description 1
CJDWRQLODFKPEL-UHFFFAOYSA-N teflubenzuron Chemical compound FC1=CC=CC(F)=C1C(=O)NC(=O)NC1=CC(Cl)=C(F)C(Cl)=C1F CJDWRQLODFKPEL-UHFFFAOYSA-N 0.000 description 1
WWJZWCUNLNYYAU-UHFFFAOYSA-N temephos Chemical compound C1=CC(OP(=S)(OC)OC)=CC=C1SC1=CC=C(OP(=S)(OC)OC)C=C1 WWJZWCUNLNYYAU-UHFFFAOYSA-N 0.000 description 1
IWVCMVBTMGNXQD-UHFFFAOYSA-N terramycin dehydrate Natural products C1=CC=C2C(O)(C)C3C(O)C4C(N(C)C)C(O)=C(C(N)=O)C(=O)C4(O)C(O)=C3C(=O)C2=C1O IWVCMVBTMGNXQD-UHFFFAOYSA-N 0.000 description 1
UBCKGWBNUIFUST-YHYXMXQVSA-N tetrachlorvinphos Chemical compound COP(=O)(OC)O\C(=C/Cl)C1=CC(Cl)=C(Cl)C=C1Cl UBCKGWBNUIFUST-YHYXMXQVSA-N 0.000 description 1
WJCNZQLZVWNLKY-UHFFFAOYSA-N thiabendazole Chemical compound S1C=NC(C=2NC3=CC=CC=C3N=2)=C1 WJCNZQLZVWNLKY-UHFFFAOYSA-N 0.000 description 1
229960004546 thiabendazole Drugs 0.000 description 1
QGHREAKMXXNCOA-UHFFFAOYSA-N thiophanate-methyl Chemical compound COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC QGHREAKMXXNCOA-UHFFFAOYSA-N 0.000 description 1
229960002447 thiram Drugs 0.000 description 1
KUAZQDVKQLNFPE-UHFFFAOYSA-N thiram Chemical compound CN(C)C(=S)SSC(=S)N(C)C KUAZQDVKQLNFPE-UHFFFAOYSA-N 0.000 description 1
229940074152 thuringiensin Drugs 0.000 description 1
OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
OBZIQQJJIKNWNO-UHFFFAOYSA-N tolclofos-methyl Chemical compound COP(=S)(OC)OC1=C(Cl)C=C(C)C=C1Cl OBZIQQJJIKNWNO-UHFFFAOYSA-N 0.000 description 1
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical class CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
YWSCPYYRJXKUDB-KAKFPZCNSA-N tralomethrin Chemical compound CC1(C)[C@@H](C(Br)C(Br)(Br)Br)[C@H]1C(=O)O[C@H](C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 YWSCPYYRJXKUDB-KAKFPZCNSA-N 0.000 description 1
229940055764 triaz Drugs 0.000 description 1
NKNFWVNSBIXGLL-UHFFFAOYSA-N triazamate Chemical compound CCOC(=O)CSC1=NC(C(C)(C)C)=NN1C(=O)N(C)C NKNFWVNSBIXGLL-UHFFFAOYSA-N 0.000 description 1
AMFGTOFWMRQMEM-UHFFFAOYSA-N triazophos Chemical compound N1=C(OP(=S)(OCC)OCC)N=CN1C1=CC=CC=C1 AMFGTOFWMRQMEM-UHFFFAOYSA-N 0.000 description 1
IQGKIPDJXCAMSM-UHFFFAOYSA-N triazoxide Chemical compound N=1C2=CC=C(Cl)C=C2[N+]([O-])=NC=1N1C=CN=C1 IQGKIPDJXCAMSM-UHFFFAOYSA-N 0.000 description 1
NFACJZMKEDPNKN-UHFFFAOYSA-N trichlorfon Chemical compound COP(=O)(OC)C(O)C(Cl)(Cl)Cl NFACJZMKEDPNKN-UHFFFAOYSA-N 0.000 description 1
DQJCHOQLCLEDLL-UHFFFAOYSA-N tricyclazole Chemical compound CC1=CC=CC2=C1N1C=NN=C1S2 DQJCHOQLCLEDLL-UHFFFAOYSA-N 0.000 description 1
XAIPTRIXGHTTNT-UHFFFAOYSA-N triflumuron Chemical compound C1=CC(OC(F)(F)F)=CC=C1NC(=O)NC(=O)C1=CC=CC=C1Cl XAIPTRIXGHTTNT-UHFFFAOYSA-N 0.000 description 1
125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 description 1
RROQIUMZODEXOR-UHFFFAOYSA-N triforine Chemical compound O=CNC(C(Cl)(Cl)Cl)N1CCN(C(NC=O)C(Cl)(Cl)Cl)CC1 RROQIUMZODEXOR-UHFFFAOYSA-N 0.000 description 1
JARYYMUOCXVXNK-CSLFJTBJSA-N validamycin A Chemical compound N([C@H]1C[C@@H]([C@H]([C@H](O)[C@H]1O)O[C@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)O)CO)[C@H]1C=C(CO)[C@@H](O)[C@H](O)[C@H]1O JARYYMUOCXVXNK-CSLFJTBJSA-N 0.000 description 1
LESVOLZBIFDZGS-UHFFFAOYSA-N vamidothion Chemical compound CNC(=O)C(C)SCCSP(=O)(OC)OC LESVOLZBIFDZGS-UHFFFAOYSA-N 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
238000005406 washing Methods 0.000 description 1
239000002699 waste material Substances 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1
210000002268 wool Anatomy 0.000 description 1
WCJYTPVNMWIZCG-UHFFFAOYSA-N xylylcarb Chemical compound CNC(=O)OC1=CC=C(C)C(C)=C1 WCJYTPVNMWIZCG-UHFFFAOYSA-N 0.000 description 1
150000003751 zinc Chemical class 0.000 description 1
DUBNHZYBDBBJHD-UHFFFAOYSA-L ziram Chemical compound [Zn+2].CN(C)C([S-])=S.CN(C)C([S-])=S DUBNHZYBDBBJHD-UHFFFAOYSA-L 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D275/00—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings
- C07D275/02—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings not condensed with other rings
- C07D275/03—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings not condensed with other rings 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
- 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
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/80—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2

Landscapes

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

JP10505570A 1996-07-16 1997-07-03 置換されたｎ―（５―イソチアゾリル）チオアミド類 Pending JP2000515135A (ja)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
DE1996128569 DE19628569A1 (de)	1996-07-16	1996-07-16	Substituierte N-(5-Isothiazolyl)-thioamide
DE19628569.0		1996-07-16
PCT/EP1997/003523 WO1998002424A1 (de)	1996-07-16	1997-07-03	Substituierte n-(5-isothiazolyl)-thioamide

Publications (1)

Publication Number	Publication Date
JP2000515135A true JP2000515135A (ja)	2000-11-14

Family

ID=7799918

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP10505570A Pending JP2000515135A (ja)	1996-07-16	1997-07-03	置換されたｎ―（５―イソチアゾリル）チオアミド類

Country Status (7)

Country	Link
EP (1)	EP0912532A1 (pt)
JP (1)	JP2000515135A (pt)
CN (1)	CN1225632A (pt)
AU (1)	AU3541097A (pt)
BR (1)	BR9710322A (pt)
DE (1)	DE19628569A1 (pt)
WO (1)	WO1998002424A1 (pt)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JP2002521480A (ja) *	1998-07-30	2002-07-16	シンジェンタリミテッド	ベンザゾール類：ベンズオキサゾール、ベンズチアゾール及びベンズイミダゾール誘導体類

Families Citing this family (9)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE19846008A1 (de)	1998-10-06	2000-04-13	Bayer Ag	Phenylessigsäure-heterocyclylamide
GB0002034D0 (en) *	2000-01-28	2000-03-22	Zeneca Ltd	Chemical compounds
GB0002036D0 (en) *	2000-01-28	2000-03-22	Zeneca Ltd	Chemical compounds
PE20010830A1 (es) *	2000-01-28	2001-09-06	Syngenta Ltd	Derivados de azol insecticidas o fungicidas y composiciones que los comprenden
GB0002029D0 (en) *	2000-01-28	2000-03-22	Zeneca Ltd	Chemical compounds
AU3034801A (en) *	2000-01-28	2001-08-07	Syngenta Limited	Isothiazole derivatives and their use as pesticides
GB0002040D0 (en) *	2000-01-28	2000-03-22	Zeneca Ltd	Chemical compounds
WO2005040162A1 (en) *	2003-10-27	2005-05-06	Basf Aktiengesellschaft	5-(2-arylacetamido)isothiazole compounds i
AP2373A (en)	2004-08-26	2012-03-07	Pfizer	Enantiomerically pure aminoheteroaryl compounds asprotein kinase inhibitors.

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE1595992A1 (de) *	1966-04-06	1970-02-12	Merck Ag E	Neue 3-Chlor-4-cyan-isothiazole und diese enthaltende insektizide Mittel
DE1954179A1 (de) *	1969-10-28	1971-05-06	Merck Anlagen Gmbh	Acylaminoisothiazolsalze
AU2641295A (en) *	1994-05-17	1995-12-05	Dowelanco	N-(5-isothiazolyl)amide pesticides
JPH08245561A (ja) *	1995-03-09	1996-09-24	Takeda Chem Ind Ltd	殺有害生物活性チオアミド誘導体、イソチアゾール誘導体、それらの用途
DE19542372A1 (de) *	1995-11-14	1997-05-15	Bayer Ag	Acylierte 5-Aminoisothiazole

1996
- 1996-07-16 DE DE1996128569 patent/DE19628569A1/de not_active Withdrawn
1997
- 1997-07-03 JP JP10505570A patent/JP2000515135A/ja active Pending
- 1997-07-03 AU AU35410/97A patent/AU3541097A/en not_active Abandoned
- 1997-07-03 EP EP97931766A patent/EP0912532A1/de not_active Withdrawn
- 1997-07-03 CN CN 97196503 patent/CN1225632A/zh active Pending
- 1997-07-03 WO PCT/EP1997/003523 patent/WO1998002424A1/de not_active Application Discontinuation
- 1997-07-03 BR BR9710322A patent/BR9710322A/pt unknown

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JP2002521480A (ja) *	1998-07-30	2002-07-16	シンジェンタリミテッド	ベンザゾール類：ベンズオキサゾール、ベンズチアゾール及びベンズイミダゾール誘導体類

Also Published As

Publication number	Publication date
CN1225632A (zh)	1999-08-11
BR9710322A (pt)	1999-08-17
EP0912532A1 (de)	1999-05-06
DE19628569A1 (de)	1998-01-22
WO1998002424A1 (de)	1998-01-22
AU3541097A (en)	1998-02-09

Publication	Publication Date	Title
EP0942904B1 (de)	2004-06-23	3-thiocarbamoylpyrazol-derivate als pestiziden
EP0861241B1 (de)	2004-04-14	Acylierte 5-aminoisothiazole mit insektizider wirkung, zwischenprodukte und verfahren zu ihrer herstellung
DE19601139A1 (de)	1997-07-17	Acylierte 5-Amino-1,2,4-thiadiazole
EP0873323B1 (de)	2002-08-28	Substituierte thiazoline und ihre verwendung zur bekämpfung von tierischen schädlingen
JP2000515135A (ja)	2000-11-14	置換されたｎ―（５―イソチアゾリル）チオアミド類
KR20000029574A (ko)	2000-05-25	치환ｎ-이소티아졸일-(티오)아미드
ES2231795T3 (es)	2005-05-16	Tetrahidro-5-nitro-pirimidinas sustituidas y su empleo para la lucha contra las pestes animales.
EP0970059B1 (de)	2003-08-20	Disubstituierte biphenyloxazoline
US5994551A (en)	1999-11-30	1-heterocyclyl methyl-2-nitro-or-cyanoiminidazoline salts, process for their preparation, pesticidal composition containing them, and pesticidal method of using them
EP0980361A1 (de)	2000-02-23	Substituierte diphenyl-oxazolin-derivate mit insektizider wirkung
EP0885225B1 (de)	2002-01-23	Tetrahydropyrimidin-derivate
JPH10508592A (ja)	1998-08-25	フルオロブテニルエステル類および動物の有害生物を抑制するためのそれらの使用
EP0944608B1 (de)	2003-04-16	4-cyclohexylphenyl-oxazoline und ihre verwendung zur bekämpfung von tierischen schädlingen
KR100492505B1 (ko)	2006-03-28	테트라하이드로피리미딘유도체
DE19625263A1 (de)	1998-01-02	Substituierte N-(4-Pyridyl)-thioamide
DE19750403A1 (de)	1999-05-20	Acylierte 4-Amino-pyridin-Derivate
JP2001523667A (ja)	2001-11-27	縮合ピリジン誘導体
DE19750402A1 (de)	1999-05-20	Acylierte 4-Amino-pyridine
CA2245875A1 (en)	1997-08-21	Salts from imidazoline derivatives and their use as a parasite control agent
DE19757223A1 (de)	1999-06-24	Disubstituierte Biphenyloxazoline
MXPA99000423A (en)	1999-09-20	N- (5-isotiazolyl) -tioamides substitui
DE19544798A1 (de)	1997-06-05	Substituierte 3-Thiocarbamoyl-5-amino-pyrazole
DE19718522A1 (de)	1998-09-10	Disubstituierte Biphenyloxazoline

JP2000515135A - 置換されたｎ―（５―イソチアゾリル）チオアミド類 - Google Patents

Info

Links

Classifications

Landscapes

Applications Claiming Priority (3)

Publications (1)

Family

ID=7799918

Family Applications (1)

Country Status (7)

Cited By (1)

Families Citing this family (9)

Family Cites Families (5)

Cited By (1)

Also Published As

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