JP2004002263A5 - - Google Patents
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- JP2004002263A5 JP2004002263A5 JP2002236164A JP2002236164A JP2004002263A5 JP 2004002263 A5 JP2004002263 A5 JP 2004002263A5 JP 2002236164 A JP2002236164 A JP 2002236164A JP 2002236164 A JP2002236164 A JP 2002236164A JP 2004002263 A5 JP2004002263 A5 JP 2004002263A5
- Authority
- JP
- Japan
- Prior art keywords
- group
- atom
- substituent
- alkyl
- substituted
- Prior art date
- 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.)
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- 125000001424 substituent group Chemical group 0.000 claims description 298
- 125000005843 halogen group Chemical group 0.000 claims description 103
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 95
- 229910052801 chlorine Inorganic materials 0.000 claims description 93
- 125000001153 fluoro group Chemical group F* 0.000 claims description 87
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 81
- 229910052731 fluorine Inorganic materials 0.000 claims description 79
- 125000000217 alkyl group Chemical group 0.000 claims description 73
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 52
- 150000001875 compounds Chemical class 0.000 claims description 46
- 150000003839 salts Chemical class 0.000 claims description 46
- -1 pyridazinyloxy Chemical group 0.000 claims description 45
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 44
- 150000002148 esters Chemical class 0.000 claims description 41
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 40
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 31
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 30
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 29
- 125000003545 alkoxy group Chemical group 0.000 claims description 28
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 26
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 26
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 26
- 125000004434 sulfur atom Chemical group 0.000 claims description 24
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 23
- 125000000623 heterocyclic group Chemical group 0.000 claims description 23
- 229910052757 nitrogen Inorganic materials 0.000 claims description 23
- 229910052717 sulfur Inorganic materials 0.000 claims description 22
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 21
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 18
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 18
- 125000001188 haloalkyl group Chemical group 0.000 claims description 18
- 229910052740 iodine Inorganic materials 0.000 claims description 18
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 15
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 14
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 13
- 125000004432 carbon atom Chemical group C* 0.000 claims description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 8
- 230000002363 herbicidal effect Effects 0.000 claims description 6
- 125000006569 (C5-C6) heterocyclic group Chemical group 0.000 claims description 5
- 125000000676 alkoxyimino group Chemical group 0.000 claims description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 5
- 229910052794 bromium Inorganic materials 0.000 claims description 5
- 125000004043 oxo group Chemical group O=* 0.000 claims description 5
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
- 125000003277 amino group Chemical group 0.000 claims description 4
- 150000001602 bicycloalkyls Chemical group 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
- 239000000460 chlorine Substances 0.000 claims description 4
- 239000000203 mixture Substances 0.000 claims description 4
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims description 4
- ASRAWSBMDXVNLX-UHFFFAOYSA-N pyrazolynate Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(=O)C=1C(C)=NN(C)C=1OS(=O)(=O)C1=CC=C(C)C=C1 ASRAWSBMDXVNLX-UHFFFAOYSA-N 0.000 claims description 4
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 3
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000002541 furyl group Chemical group 0.000 claims description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
- 125000001544 thienyl group Chemical group 0.000 claims description 3
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
- LNGRZPZKVUBWQV-UHFFFAOYSA-N (4-chloro-2-methylsulfonylphenyl)-(5-cyclopropyl-1,2-oxazol-4-yl)methanone Chemical compound CS(=O)(=O)C1=CC(Cl)=CC=C1C(=O)C1=C(C2CC2)ON=C1 LNGRZPZKVUBWQV-UHFFFAOYSA-N 0.000 claims description 2
- CJSZUDRFDBPZFG-UHFFFAOYSA-N 3-(1-benzofuran-7-yloxy)-6-chloro-1h-pyridazin-4-one Chemical compound OC1=CC(Cl)=NN=C1OC1=CC=CC2=C1OC=C2 CJSZUDRFDBPZFG-UHFFFAOYSA-N 0.000 claims description 2
- YLBGKIGQWGWJAV-UHFFFAOYSA-N 3-(2-bromo-6-methylphenoxy)-6-chloro-1h-pyridazin-4-one Chemical compound CC1=CC=CC(Br)=C1OC1=NN=C(Cl)C=C1O YLBGKIGQWGWJAV-UHFFFAOYSA-N 0.000 claims description 2
- IWKQMRRGGSDCBA-UHFFFAOYSA-N 3-phenoxy-1h-pyridazin-4-one Chemical class OC1=CC=NN=C1OC1=CC=CC=C1 IWKQMRRGGSDCBA-UHFFFAOYSA-N 0.000 claims description 2
- NREOCHFMYBRODV-UHFFFAOYSA-N 6-chloro-3-(2,3-dihydro-1h-inden-4-yloxy)-1h-pyridazin-4-one Chemical compound OC1=CC(Cl)=NN=C1OC1=CC=CC2=C1CCC2 NREOCHFMYBRODV-UHFFFAOYSA-N 0.000 claims description 2
- MDOUHXIYRZVOBZ-UHFFFAOYSA-N 6-chloro-3-(2-chloro-6-cyclopropylphenoxy)-1h-pyridazin-4-one Chemical compound OC1=CC(Cl)=NN=C1OC1=C(Cl)C=CC=C1C1CC1 MDOUHXIYRZVOBZ-UHFFFAOYSA-N 0.000 claims description 2
- VXILURWSAZHSSO-UHFFFAOYSA-N 6-chloro-3-(2-iodophenoxy)-1h-pyridazin-4-one Chemical compound OC1=CC(Cl)=NN=C1OC1=CC=CC=C1I VXILURWSAZHSSO-UHFFFAOYSA-N 0.000 claims description 2
- QZIJCVNSXFTMKH-UHFFFAOYSA-N 6-chloro-3-(2-methoxy-5-methylphenoxy)-1h-pyridazin-4-one Chemical compound COC1=CC=C(C)C=C1OC1=NN=C(Cl)C=C1O QZIJCVNSXFTMKH-UHFFFAOYSA-N 0.000 claims description 2
- QFFRMJJGHVACFL-UHFFFAOYSA-N 6-chloro-3-(2-methylphenoxy)-1h-pyridazin-4-one Chemical compound CC1=CC=CC=C1OC1=NN=C(Cl)C=C1O QFFRMJJGHVACFL-UHFFFAOYSA-N 0.000 claims description 2
- JDWQITFHZOBBFE-UHFFFAOYSA-N Benzofenap Chemical compound C=1C=C(Cl)C(C)=C(Cl)C=1C(=O)C=1C(C)=NN(C)C=1OCC(=O)C1=CC=C(C)C=C1 JDWQITFHZOBBFE-UHFFFAOYSA-N 0.000 claims description 2
- 239000004480 active ingredient Substances 0.000 claims description 2
- HJSLFCCWAKVHIW-UHFFFAOYSA-N cyclohexane-1,3-dione Chemical compound O=C1CCCC(=O)C1 HJSLFCCWAKVHIW-UHFFFAOYSA-N 0.000 claims description 2
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 2
- 125000005842 heteroatom Chemical group 0.000 claims description 2
- PQTBTIFWAXVEPB-UHFFFAOYSA-N sulcotrione Chemical compound ClC1=CC(S(=O)(=O)C)=CC=C1C(=O)C1C(=O)CCCC1=O PQTBTIFWAXVEPB-UHFFFAOYSA-N 0.000 claims description 2
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 13
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 13
- 125000006583 (C1-C3) haloalkyl group Chemical group 0.000 claims 7
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 6
- 125000006828 (C2-C7) alkoxycarbonyl group Chemical group 0.000 claims 5
- 125000006773 (C2-C7) alkylcarbonyl group Chemical group 0.000 claims 5
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 4
- 125000004738 (C1-C6) alkyl sulfinyl group Chemical group 0.000 claims 3
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims 3
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims 3
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 3
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 3
- 125000004455 (C1-C3) alkylthio group Chemical group 0.000 claims 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 2
- 125000004844 (C1-C6) alkoxyimino group Chemical group 0.000 claims 2
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims 2
- 125000006645 (C3-C4) cycloalkyl group Chemical group 0.000 claims 2
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 claims 2
- 125000006677 (C1-C3) haloalkoxy group Chemical group 0.000 claims 1
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 125000001246 bromo group Chemical group Br* 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 40
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 18
- 125000004448 alkyl carbonyl group Chemical group 0.000 description 16
- 125000004414 alkyl thio group Chemical group 0.000 description 7
- 125000002252 acyl group Chemical group 0.000 description 6
- 125000003342 alkenyl group Chemical group 0.000 description 5
- 239000000126 substance Substances 0.000 description 4
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 3
- 125000004438 haloalkoxy group Chemical group 0.000 description 3
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical group C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 3
- PRQKVXNVZPBESR-UHFFFAOYSA-N 2-cyclopropyl-6-methylphenol Chemical compound CC1=CC=CC(C2CC2)=C1O PRQKVXNVZPBESR-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
- 125000005092 alkenyloxycarbonyl group Chemical group 0.000 description 2
- 125000000304 alkynyl group Chemical group 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- BBUOLWPYQKZWIU-UHFFFAOYSA-N [6-chloro-3-(2-cyclopropyl-6-methylphenoxy)pyridazin-4-yl] 4-methylbenzenesulfonate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)OC1=CC(Cl)=NN=C1OC1=C(C)C=CC=C1C1CC1 BBUOLWPYQKZWIU-UHFFFAOYSA-N 0.000 description 1
- YYMDWGQAXMPNQX-UHFFFAOYSA-N [6-chloro-3-(2-cyclopropyl-6-methylphenoxy)pyridazin-4-yl] 4-methylbenzoate Chemical compound C1=CC(C)=CC=C1C(=O)OC1=CC(Cl)=NN=C1OC1=C(C)C=CC=C1C1CC1 YYMDWGQAXMPNQX-UHFFFAOYSA-N 0.000 description 1
- ZKCQNECTCYNPOQ-UHFFFAOYSA-N [6-chloro-3-(2-cyclopropyl-6-methylphenoxy)pyridazin-4-yl] azetidine-1-carboxylate Chemical compound N=1N=C(Cl)C=C(OC(=O)N2CCC2)C=1OC=1C(C)=CC=CC=1C1CC1 ZKCQNECTCYNPOQ-UHFFFAOYSA-N 0.000 description 1
- YJQJJMJXEOWOIZ-UHFFFAOYSA-N [6-chloro-3-(2-cyclopropyl-6-methylphenoxy)pyridazin-4-yl] propane-1-sulfonate Chemical compound CCCS(=O)(=O)OC1=CC(Cl)=NN=C1OC1=C(C)C=CC=C1C1CC1 YJQJJMJXEOWOIZ-UHFFFAOYSA-N 0.000 description 1
- 125000005090 alkenylcarbonyl group Chemical group 0.000 description 1
- 125000005108 alkenylthio group Chemical group 0.000 description 1
- 125000005530 alkylenedioxy group Chemical group 0.000 description 1
- 125000005087 alkynylcarbonyl group Chemical group 0.000 description 1
- 125000006254 cycloalkyl carbonyl group Chemical group 0.000 description 1
- BXIGJZDQFDFASM-UHFFFAOYSA-N cyclopyrimorate Chemical compound N=1N=C(Cl)C=C(OC(=O)N2CCOCC2)C=1OC=1C(C)=CC=CC=1C1CC1 BXIGJZDQFDFASM-UHFFFAOYSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 125000001038 naphthoyl group Chemical group C1(=CC=CC2=CC=CC=C12)C(=O)* 0.000 description 1
- 125000006678 phenoxycarbonyl group Chemical group 0.000 description 1
- 125000003003 spiro group Chemical group 0.000 description 1
- BZLZKLMROPIZSR-UHFFFAOYSA-N triphenylsilicon Chemical group C1=CC=CC=C1[Si](C=1C=CC=CC=1)C1=CC=CC=C1 BZLZKLMROPIZSR-UHFFFAOYSA-N 0.000 description 1
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2002236164A JP4128048B2 (ja) | 2001-08-17 | 2002-08-14 | ３−フェノキシ−４−ピリダジノール誘導体及びそれを含有する除草剤組成物 |
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2001248014 | 2001-08-17 | ||
| JP2002082219 | 2002-03-25 | ||
| JP2002236164A JP4128048B2 (ja) | 2001-08-17 | 2002-08-14 | ３−フェノキシ−４−ピリダジノール誘導体及びそれを含有する除草剤組成物 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2004002263A JP2004002263A (ja) | 2004-01-08 |
| JP2004002263A5 true JP2004002263A5 (https=) | 2007-08-30 |
| JP4128048B2 JP4128048B2 (ja) | 2008-07-30 |
Family
ID=30449020
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2002236164A Expired - Lifetime JP4128048B2 (ja) | 2001-08-17 | 2002-08-14 | ３−フェノキシ−４−ピリダジノール誘導体及びそれを含有する除草剤組成物 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP4128048B2 (https=) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP4567345B2 (ja) * | 2003-02-12 | 2010-10-20 | 三井化学アグロ株式会社 | ３−フェノキシ−４−ピリダジノール誘導体を含有する農薬 |
| JP4580173B2 (ja) * | 2003-02-13 | 2010-11-10 | 三井化学アグロ株式会社 | ３−フェノキシ−４−ピリダジノール化合物を含有する除草組成物 |
| JP4580174B2 (ja) * | 2003-02-13 | 2010-11-10 | 三井化学アグロ株式会社 | ３−フェノキシ−４−ピリダジノール化合物を含有する除草性組成物 |
| JP4580175B2 (ja) * | 2003-02-13 | 2010-11-10 | 三井化学アグロ株式会社 | ３−フェノキシ−４−ピリダジノール誘導体を含有する除草剤組成物 |
| JP4580172B2 (ja) * | 2003-02-13 | 2010-11-10 | 三井化学アグロ株式会社 | ３−フェノキシ−４−ピリダジノール化合物を含有する除草剤組成物 |
| JP4549690B2 (ja) * | 2003-02-13 | 2010-09-22 | 三井化学アグロ株式会社 | ３−フェノキシ−４−ピリダジノール誘導体を含有する除草性組成物 |
| JP4580176B2 (ja) * | 2003-02-13 | 2010-11-10 | 三井化学アグロ株式会社 | ３−フェノキシ−４−ピリダジノール誘導体を含有する除草組成物 |
| JP4580171B2 (ja) * | 2003-02-13 | 2010-11-10 | 三井化学アグロ株式会社 | ３−フェノキシ−４−ピリダジノール誘導体を含有する除草性組成物 |
| KR101307721B1 (ko) * | 2005-03-31 | 2013-09-11 | 미쓰이가가쿠 아그로 가부시키가이샤 | 시클로프로필페놀 유도체의 제조법 |
| JP5106839B2 (ja) * | 2006-11-30 | 2012-12-26 | 三井化学アグロ株式会社 | 除草性組成物 |
| US8552182B2 (en) | 2009-09-30 | 2013-10-08 | Mitsui Chemicals Agro, Inc. | Method for producing a 3-(substituted-oxy)-4-pyridazinol derivative |
| JP6029995B2 (ja) * | 2013-02-04 | 2016-11-24 | クミアイ化学工業株式会社 | 除草剤組成物 |
| AR117169A1 (es) * | 2018-11-28 | 2021-07-14 | Bayer Ag | (tio)amidas de piridazina como compuestos fungicidas |
-
2002
- 2002-08-14 JP JP2002236164A patent/JP4128048B2/ja not_active Expired - Lifetime
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