JP2018513870A5 - - Google Patents
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- JP2018513870A5 JP2018513870A5 JP2017555483A JP2017555483A JP2018513870A5 JP 2018513870 A5 JP2018513870 A5 JP 2018513870A5 JP 2017555483 A JP2017555483 A JP 2017555483A JP 2017555483 A JP2017555483 A JP 2017555483A JP 2018513870 A5 JP2018513870 A5 JP 2018513870A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- haloalkyl
- formula
- group
- halogen
- 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.)
- Ceased
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- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 71
- 229910052736 halogen Inorganic materials 0.000 claims description 44
- 150000002367 halogens Chemical group 0.000 claims description 44
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 40
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 37
- 150000001875 compounds Chemical class 0.000 claims description 36
- 125000004770 (C1-C4) haloalkylsulfanyl group Chemical group 0.000 claims description 34
- 125000004771 (C1-C4) haloalkylsulfinyl group Chemical group 0.000 claims description 32
- 125000001424 substituent group Chemical group 0.000 claims description 30
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims description 28
- 229910052757 nitrogen Inorganic materials 0.000 claims description 22
- 229910052739 hydrogen Inorganic materials 0.000 claims description 20
- 239000001257 hydrogen Substances 0.000 claims description 20
- 229910052717 sulfur Inorganic materials 0.000 claims description 20
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 19
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 18
- 229910052760 oxygen Inorganic materials 0.000 claims description 18
- 239000001301 oxygen Substances 0.000 claims description 18
- 239000011593 sulfur Substances 0.000 claims description 18
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 16
- -1 C 1 -C 4 alkoxy Chemical group 0.000 claims description 15
- 125000004441 haloalkylsulfonyl group Chemical group 0.000 claims description 15
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 15
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims description 14
- 125000004122 cyclic group Chemical group 0.000 claims description 14
- 125000004768 (C1-C4) alkylsulfinyl group Chemical group 0.000 claims description 13
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 8
- 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 8
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 7
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 7
- 125000001188 haloalkyl group Chemical group 0.000 claims description 7
- 241000607479 Yersinia pestis Species 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 5
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 4
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 4
- 125000005842 heteroatom Chemical group 0.000 claims description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims description 4
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims description 4
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- 229920006395 saturated elastomer Polymers 0.000 claims description 4
- 125000004434 sulfur atom Chemical group 0.000 claims description 4
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 3
- 125000006643 (C2-C6) haloalkenyl group Chemical group 0.000 claims description 2
- XDGUAGHLBCQNGD-UHFFFAOYSA-N 2-bromo-5-ethylsulfonyl-4-[3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridin-2-yl]-1,3-thiazole Chemical compound BrC=1SC(=C(N=1)C1=NC2=C(C=NC(=C2)C(F)(F)F)N1C)S(=O)(=O)CC XDGUAGHLBCQNGD-UHFFFAOYSA-N 0.000 claims description 2
- 125000006414 CCl Chemical group ClC* 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 150000001204 N-oxides Chemical class 0.000 claims description 2
- 239000004480 active ingredient Substances 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 230000000361 pesticidal effect Effects 0.000 claims description 2
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 9
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 2
- 125000004429 atom Chemical group 0.000 claims 1
- 125000004440 haloalkylsulfinyl group Chemical group 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 description 36
- 125000003545 alkoxy group Chemical group 0.000 description 13
- 0 CC1N=CN=CC*1 Chemical compound CC1N=CN=CC*1 0.000 description 12
- 150000002431 hydrogen Chemical group 0.000 description 9
- 125000004414 alkyl thio group Chemical group 0.000 description 7
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 1
- ODLMAHJVESYWTB-UHFFFAOYSA-N CCCc1ccccc1 Chemical compound CCCc1ccccc1 ODLMAHJVESYWTB-UHFFFAOYSA-N 0.000 description 1
- OIALIKXMLIAOSN-UHFFFAOYSA-N CCCc1ccccn1 Chemical compound CCCc1ccccn1 OIALIKXMLIAOSN-UHFFFAOYSA-N 0.000 description 1
- YVHDMQRVTVCDAS-UHFFFAOYSA-N CCCc1ncccn1 Chemical compound CCCc1ncccn1 YVHDMQRVTVCDAS-UHFFFAOYSA-N 0.000 description 1
- SEAZNTDWFMFOKA-UHFFFAOYSA-N CC[n]1cnnc1 Chemical compound CC[n]1cnnc1 SEAZNTDWFMFOKA-UHFFFAOYSA-N 0.000 description 1
- FEOIYPLRWRCSMS-UHFFFAOYSA-N CC[n]1ncnc1 Chemical compound CC[n]1ncnc1 FEOIYPLRWRCSMS-UHFFFAOYSA-N 0.000 description 1
- GQPBBURQQRLAKF-UHFFFAOYSA-N CCc1c[o]cn1 Chemical compound CCc1c[o]cn1 GQPBBURQQRLAKF-UHFFFAOYSA-N 0.000 description 1
- AVFZOVWCLRSYKC-UHFFFAOYSA-N CN1CCCC1 Chemical compound CN1CCCC1 AVFZOVWCLRSYKC-UHFFFAOYSA-N 0.000 description 1
- PAMIQIKDUOTOBW-UHFFFAOYSA-N CN1CCCCC1 Chemical compound CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 description 1
- UQFQONCQIQEYPJ-UHFFFAOYSA-N C[n]1nccc1 Chemical compound C[n]1nccc1 UQFQONCQIQEYPJ-UHFFFAOYSA-N 0.000 description 1
- LMYVCXSKCQSIEQ-UHFFFAOYSA-N Cc1c(cccn2)c2ccc1 Chemical compound Cc1c(cccn2)c2ccc1 LMYVCXSKCQSIEQ-UHFFFAOYSA-N 0.000 description 1
- CQLOYHZZZCWHSG-UHFFFAOYSA-N Cc1c2nccnc2ccc1 Chemical compound Cc1c2nccnc2ccc1 CQLOYHZZZCWHSG-UHFFFAOYSA-N 0.000 description 1
- RIKMMFOAQPJVMX-UHFFFAOYSA-N Cc1c[nH]nc1 Chemical compound Cc1c[nH]nc1 RIKMMFOAQPJVMX-UHFFFAOYSA-N 0.000 description 1
- VQKFNUFAXTZWDK-UHFFFAOYSA-N Cc1ccc[o]1 Chemical compound Cc1ccc[o]1 VQKFNUFAXTZWDK-UHFFFAOYSA-N 0.000 description 1
- MXDRPNGTQDRKQM-UHFFFAOYSA-N Cc1cccnn1 Chemical compound Cc1cccnn1 MXDRPNGTQDRKQM-UHFFFAOYSA-N 0.000 description 1
- AIKUBOPKWKZULG-UHFFFAOYSA-N Cc1ccnnc1 Chemical compound Cc1ccnnc1 AIKUBOPKWKZULG-UHFFFAOYSA-N 0.000 description 1
- ALHUXMDEZNLFTA-UHFFFAOYSA-N Cc1cnc(cccc2)c2n1 Chemical compound Cc1cnc(cccc2)c2n1 ALHUXMDEZNLFTA-UHFFFAOYSA-N 0.000 description 1
- TWGNOYAGHYUFFR-UHFFFAOYSA-N Cc1cncnc1 Chemical compound Cc1cncnc1 TWGNOYAGHYUFFR-UHFFFAOYSA-N 0.000 description 1
- FZAXBPZVVJOFKX-UHFFFAOYSA-N Cc1n[o]cn1 Chemical compound Cc1n[o]cn1 FZAXBPZVVJOFKX-UHFFFAOYSA-N 0.000 description 1
- IBANRDPEOYZVGW-UHFFFAOYSA-N Cc1n[s]cn1 Chemical compound Cc1n[s]cn1 IBANRDPEOYZVGW-UHFFFAOYSA-N 0.000 description 1
- DXPQTHAFYUTZRR-UHFFFAOYSA-N Cc1ncc(cccc2)c2n1 Chemical compound Cc1ncc(cccc2)c2n1 DXPQTHAFYUTZRR-UHFFFAOYSA-N 0.000 description 1
- VZWOXDYRBDIHMA-UHFFFAOYSA-N Cc1ncc[s]1 Chemical compound Cc1ncc[s]1 VZWOXDYRBDIHMA-UHFFFAOYSA-N 0.000 description 1
- LNJMHEJAYSYZKK-UHFFFAOYSA-N Cc1ncccn1 Chemical compound Cc1ncccn1 LNJMHEJAYSYZKK-UHFFFAOYSA-N 0.000 description 1
- CAWHJQAVHZEVTJ-UHFFFAOYSA-N Cc1nccnc1 Chemical compound Cc1nccnc1 CAWHJQAVHZEVTJ-UHFFFAOYSA-N 0.000 description 1
- LVILGAOSPDLNRM-UHFFFAOYSA-N Cc1ncncc1 Chemical compound Cc1ncncc1 LVILGAOSPDLNRM-UHFFFAOYSA-N 0.000 description 1
- ZMSIFDIKIXVLDF-UHFFFAOYSA-N Cc1nnc[o]1 Chemical compound Cc1nnc[o]1 ZMSIFDIKIXVLDF-UHFFFAOYSA-N 0.000 description 1
- RQSCFNPNNLWQBJ-UHFFFAOYSA-N Cc1nnc[s]1 Chemical compound Cc1nnc[s]1 RQSCFNPNNLWQBJ-UHFFFAOYSA-N 0.000 description 1
- 125000004644 alkyl sulfinyl group Chemical group 0.000 description 1
- 238000002405 diagnostic procedure Methods 0.000 description 1
- 230000000749 insecticidal effect Effects 0.000 description 1
- 125000002950 monocyclic group Chemical group 0.000 description 1
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 1
- 238000001356 surgical procedure Methods 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2015077330 | 2015-04-24 | ||
| CNPCT/CN2015/077330 | 2015-04-24 | ||
| PCT/EP2016/058534 WO2016169886A1 (en) | 2015-04-24 | 2016-04-18 | Pesticidally active polycyclic derivatives with sulfur substituted five-membered ring heterocyles |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2018513870A JP2018513870A (ja) | 2018-05-31 |
| JP2018513870A5 true JP2018513870A5 (enExample) | 2019-05-30 |
Family
ID=55754319
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2017555483A Ceased JP2018513870A (ja) | 2015-04-24 | 2016-04-18 | 硫黄置換５員環複素環を有する殺有害生物的に活性な多環式誘導体 |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US10125139B2 (enExample) |
| EP (2) | EP3286187B1 (enExample) |
| JP (1) | JP2018513870A (enExample) |
| CN (1) | CN108040481B (enExample) |
| BR (1) | BR112017022683A2 (enExample) |
| ES (1) | ES2762947T3 (enExample) |
| WO (1) | WO2016169886A1 (enExample) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP6707630B2 (ja) | 2015-06-01 | 2020-06-10 | バンタム、ファーマシューティカル、リミテッド、ライアビリティー、カンパニーＢａｎｔａｍ Ｐｈａｒｍａｃｅｕｔｉｃａｌ， Ｌｌｃ | 置換ピラゾールおよびピロール化合物、および翻訳開始の阻害およびこれらに関連する疾患および障害の治療のためにこれらを用いる方法 |
| US12150934B2 (en) | 2016-11-30 | 2024-11-26 | Bantam Pharmaceutical, Llc | Methods of using substituted pyrazole and pyrazole compounds and for treatment of hyperproliferative diseases |
| EP3548482A4 (en) | 2016-11-30 | 2020-08-19 | Bantam Pharmaceutical, LLC | SUBSTITUTED PYRAZOLE COMPOUNDS AND THEIR METHODS OF USE FOR THE TREATMENT OF HYPERPROLIFERATIVE DISEASES |
| CA3047896C (en) | 2016-12-27 | 2021-11-09 | Nihon Nohyaku Co., Ltd. | 4h-pyrrolopyridine compound or salt thereof, agricultural and horticultural insecticide comprising the compound or the salt, and method for using the insecticide |
| MX2019008230A (es) * | 2017-01-10 | 2019-10-24 | Bayer Ag | Derivados heterociclicos como agentes de control de plagas. |
| AU2018207776B2 (en) * | 2017-01-10 | 2021-06-17 | Bayer Aktiengesellschaft | Heterocyclene derivatives as pest control agents |
| MX2019012728A (es) * | 2017-04-24 | 2020-01-23 | Bayer Ag | Derivados de heterociclos biciclicos fusionados como plaguicidas. |
| JP2020128340A (ja) * | 2017-04-27 | 2020-08-27 | 日本農薬株式会社 | ５員環の含窒素複素環化合物又はその塩類及び該化合物を含有する農園芸用殺虫剤並びにその使用方法 |
| WO2018215304A1 (en) | 2017-05-22 | 2018-11-29 | Syngenta Participations Ag | Tetracyclic pyridazine sulphur containing compounds and their use as pesticides |
| CN112262140B (zh) | 2018-06-06 | 2024-05-28 | 先正达农作物保护股份公司 | 具有含亚砜亚胺取代基的杀有害生物活性杂环衍生物 |
| JP7353310B2 (ja) | 2018-06-26 | 2023-09-29 | バイエル・アクチエンゲゼルシヤフト | 有害生物防除剤としてのヘテロサイクレン誘導体 |
| JP2023532548A (ja) | 2020-07-02 | 2023-07-28 | バイエル・アクチエンゲゼルシヤフト | 有害生物防除剤としてのヘテロサイクレン誘導体 |
| CN120882309A (zh) | 2023-03-14 | 2025-10-31 | 先正达农作物保护股份公司 | 对杀昆虫剂具有抗性的有害生物的控制 |
| WO2025026738A1 (en) | 2023-07-31 | 2025-02-06 | Bayer Aktiengesellschaft | 6-[5-(ethylsulfonyl)-1-methyl-1h-imidazol-4-yl]-7-methyl-3-(pentafluoroethyl)-7h-imidazo[4,5-c]pyridazine derivatives as pesticides |
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| UY35421A (es) * | 2013-03-15 | 2014-10-31 | Nihon Nohyaku Co Ltd | Compuesto heterocíclico condensado o su sal, insecticida agrícola u hortícola que comprende el comp uesto y método de uso del insecticida |
| WO2014148451A1 (ja) | 2013-03-19 | 2014-09-25 | 日本農薬株式会社 | 縮合複素環化合物又はその塩類及び該化合物を含有する農園芸用殺虫剤並びにその使用方法 |
| MX2015017821A (es) * | 2013-07-02 | 2016-04-15 | Syngenta Participations Ag | Heterociclos bi-o triciclicos activos como plaguicidas con sustituyentes que contienen azufre. |
| WO2016039444A1 (ja) * | 2014-09-12 | 2016-03-17 | 日本農薬株式会社 | イミダゾピリダジン化合物又はその塩類及び該化合物を含有する農園芸用殺虫剤並びにその使用方法 |
-
2016
- 2016-04-18 EP EP16716629.7A patent/EP3286187B1/en active Active
- 2016-04-18 JP JP2017555483A patent/JP2018513870A/ja not_active Ceased
- 2016-04-18 CN CN201680023352.6A patent/CN108040481B/zh not_active Expired - Fee Related
- 2016-04-18 US US15/568,817 patent/US10125139B2/en not_active Expired - Fee Related
- 2016-04-18 WO PCT/EP2016/058534 patent/WO2016169886A1/en not_active Ceased
- 2016-04-18 BR BR112017022683-9A patent/BR112017022683A2/pt not_active Application Discontinuation
- 2016-04-18 ES ES16716629T patent/ES2762947T3/es active Active
- 2016-04-18 EP EP19189330.4A patent/EP3656770A3/en not_active Withdrawn
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