CA2693067C - Method for preparing 5-haloalkyl-4,5-dihydroisoxazole derivatives - Google Patents

Method for preparing 5-haloalkyl-4,5-dihydroisoxazole derivatives Download PDF

Info

Publication number
CA2693067C
CA2693067C CA2693067A CA2693067A CA2693067C CA 2693067 C CA2693067 C CA 2693067C CA 2693067 A CA2693067 A CA 2693067A CA 2693067 A CA2693067 A CA 2693067A CA 2693067 C CA2693067 C CA 2693067C
Authority
CA
Canada
Prior art keywords
ch2c
alkyl
optionally substituted
halogen
ring
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.)
Active
Application number
CA2693067A
Other languages
English (en)
French (fr)
Other versions
CA2693067A1 (en
Inventor
Gary David Annis
Brenton Todd Smith
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.)
Corteva Agriscience LLC
Original Assignee
EI Du Pont de Nemours and Co
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.)
Filing date
Publication date
Application filed by EI Du Pont de Nemours and Co filed Critical EI Du Pont de Nemours and Co
Publication of CA2693067A1 publication Critical patent/CA2693067A1/en
Application granted granted Critical
Publication of CA2693067C publication Critical patent/CA2693067C/en
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
    • C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
    • C07D261/04—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C201/00—Preparation of esters of nitric or nitrous acid or of compounds containing nitro or nitroso groups bound to a carbon skeleton
    • C07C201/06—Preparation of nitro compounds
    • C07C201/12—Preparation of nitro compounds by reactions not involving the formation of nitro groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
    • C07C205/45—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by at least one doubly—bound oxygen atom, not being part of a —CHO group
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
    • C07C45/65—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by splitting-off hydrogen atoms or functional groups; by hydrogenolysis of functional groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
    • C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
    • C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
    • C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
    • C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
    • C07C45/72—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
    • C07C49/80—Ketones containing a keto group bound to a six-membered aromatic ring containing halogen
    • C07C49/813—Ketones containing a keto group bound to a six-membered aromatic ring containing halogen polycyclic
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
    • C07C49/82—Ketones containing a keto group bound to a six-membered aromatic ring containing hydroxy groups
    • C07C49/83—Ketones containing a keto group bound to a six-membered aromatic ring containing hydroxy groups polycyclic
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
    • C07C49/82—Ketones containing a keto group bound to a six-membered aromatic ring containing hydroxy groups
    • C07C49/835—Ketones containing a keto group bound to a six-membered aromatic ring containing hydroxy groups having unsaturation outside an aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
    • C07C49/84—Ketones containing a keto group bound to a six-membered aromatic ring containing ether groups, groups, groups, or groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C65/00—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C65/32—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing keto groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C65/00—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C65/32—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing keto groups
    • C07C65/38—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing keto groups having unsaturation outside the aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/007—Esters of unsaturated alcohols having the esterified hydroxy group bound to an acyclic carbon atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
CA2693067A 2007-08-17 2008-08-04 Method for preparing 5-haloalkyl-4,5-dihydroisoxazole derivatives Active CA2693067C (en)

Applications Claiming Priority (7)

Application Number Priority Date Filing Date Title
US96511507P 2007-08-17 2007-08-17
US60/965,115 2007-08-17
US4345908P 2008-04-09 2008-04-09
US61/043,459 2008-04-09
US8045408P 2008-07-14 2008-07-14
US61/080,454 2008-07-14
PCT/US2008/072074 WO2009025983A2 (en) 2007-08-17 2008-08-04 Method for preparing 5-haloalkyl-4,5-dihydroisoxazole derivatives

Publications (2)

Publication Number Publication Date
CA2693067A1 CA2693067A1 (en) 2009-02-26
CA2693067C true CA2693067C (en) 2016-10-11

Family

ID=40350174

Family Applications (1)

Application Number Title Priority Date Filing Date
CA2693067A Active CA2693067C (en) 2007-08-17 2008-08-04 Method for preparing 5-haloalkyl-4,5-dihydroisoxazole derivatives

Country Status (19)

Country Link
US (2) US8217180B2 (enExample)
EP (1) EP2176244B1 (enExample)
JP (2) JP5965102B2 (enExample)
KR (2) KR101597839B1 (enExample)
CN (2) CN105693646A (enExample)
AR (1) AR067948A1 (enExample)
AU (1) AU2008289321B2 (enExample)
BR (1) BRPI0814153B8 (enExample)
CA (1) CA2693067C (enExample)
CO (1) CO6260136A2 (enExample)
ES (1) ES2587386T3 (enExample)
IL (1) IL203174A (enExample)
MX (2) MX337588B (enExample)
MY (2) MY176115A (enExample)
PT (1) PT2176244T (enExample)
RU (1) RU2536039C2 (enExample)
TW (3) TWI600639B (enExample)
WO (1) WO2009025983A2 (enExample)
ZA (1) ZA201000214B (enExample)

Families Citing this family (51)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102558082B (zh) 2004-03-05 2015-09-30 日产化学工业株式会社 异噁唑啉取代苯甲酰胺化合物的制备中间体
TW200803740A (en) * 2005-12-16 2008-01-16 Du Pont 5-aryl isoxazolines for controlling invertebrate pests
TWI412322B (zh) 2005-12-30 2013-10-21 Du Pont 控制無脊椎害蟲之異唑啉
CN101815706A (zh) * 2007-06-13 2010-08-25 杜邦公司 异*唑啉杀昆虫剂
TWI430995B (zh) * 2007-06-26 2014-03-21 Du Pont 萘異唑啉無脊椎有害動物控制劑
US8952175B2 (en) 2007-06-27 2015-02-10 Nissan Chemical Industries, Ltd. Method for production of 3-hydroxypropan-1-one compound, method for production of 2-propen-1-one compound and method for production of isoxazoline compound
MX368680B (es) 2007-06-27 2019-10-11 Du Pont Administración subcutánea de un derivado de isoxazol-benzamida para usarse en un método para proteger un mamífero de una pulga.
TWI600639B (zh) * 2007-08-17 2017-10-01 杜邦股份有限公司 製備５-鹵烷基-４，５-二氫異唑衍生物之化合物
MX2010003557A (es) * 2007-10-03 2010-04-12 Du Pont Compuestos de isoxazolina de naftaleno para el control de plagas de invertebrados.
TWI518076B (zh) * 2008-04-09 2016-01-21 杜邦股份有限公司 製備雜環化合物之方法
BRPI0915665B1 (pt) 2008-07-09 2018-01-02 Basf Se Misturas pesticidas, métodos para proteger plantas do ataque ou infestação por insetos, acarídeos ou nematódeos, para controlar insetos, aracnídeos ou nematódeos, uso de uma mistura, e, composição pesticida ou parasiticida
BRPI0915818A2 (pt) 2008-07-09 2015-08-04 Basf Se Mistura pesticida, composição pesticida, método para controlar fungos nocivos fitopatogênicos, para proteger plantas de fungos nocivos fitopatogênicos, para controlar insetos, aracnídeos ou nematódeos, para proteger plantas do ataque ou infestação por insetos, acarídeos ou nematódeos, e para a proteção de semente, semente, e, uso de uma mistura.
US20110269804A1 (en) 2008-08-22 2011-11-03 Syngenta Crop Protection Llc Insecticidal compounds
EA201100356A1 (ru) 2008-08-22 2011-10-31 Зингента Партисипейшнс Аг Инсектицидные соединения
CN102143960A (zh) 2008-09-04 2011-08-03 先正达参股股份有限公司 杀虫化合物
AU2009331476B2 (en) 2008-12-23 2015-05-28 Basf Se Imine compounds for combating invertebrate pests
KR20110099139A (ko) 2008-12-23 2011-09-06 바스프 에스이 동물 해충의 퇴치를 위한 치환된 아미딘 화합물
CN102369199A (zh) * 2009-04-01 2012-03-07 巴斯夫欧洲公司 用于防治无脊椎动物害虫的异*唑啉化合物
UA108219C2 (uk) 2009-12-17 2015-04-10 Протипаразитарні дигідроазолові сполуки та композиція, яка їх містить (варіанти)
EP2531493B1 (en) 2010-02-01 2015-07-22 Basf Se Substituted ketonic isoxazoline compounds and derivatives for combating animal pests
MA34247B1 (fr) 2010-05-27 2013-05-02 Du Pont Forme cristalline du 4-[5-[3-chloro-5-(trifluorométhyl) phényl] -4,5-dihydro-5-(trifluorométhyl)-3-isoxazolyl]-n-[2-oxo-2-[(2, 2,2-trifluoroéthyl) amino] éthyl]-1-naphtalènecarboxamide
UY33403A (es) 2010-06-17 2011-12-30 Novartis Ag Compuestos orgánicos con novedosas isoxazolinas, sus n-óxidos, s-óxidos y sales
ES2793481T3 (es) 2010-09-24 2020-11-16 Zoetis Services Llc Oximas de isoxazolina como agentes antiparasitarios
EP2621894B1 (en) * 2010-09-27 2016-11-16 E. I. du Pont de Nemours and Company Method for preparing 2-amino-n-(2,2,2-trifluoroethyl) acetamide
RU2013141413A (ru) 2011-02-10 2015-03-20 Новартис Аг Производные изоксазолина для борьбы с беспозвоночными паразитами
AR085657A1 (es) 2011-03-10 2013-10-16 Novartis Ag Compuestos de isoxazol
JP6075563B2 (ja) 2011-11-08 2017-02-08 日産化学工業株式会社 光学活性イソキサゾリン化合物の触媒的不斉合成方法及び光学活性イソキサゾリン化合物
KR20140115329A (ko) 2011-12-23 2014-09-30 바스프 에스이 무척추동물 해충 퇴치를 위한 이소티아졸린 화합물
AU2013348175B2 (en) 2012-11-20 2016-11-17 Boehringer Ingelheim Animal Health USA Inc. Anthelmintic compounds and compositions and method of using thereof
AU2014342241B2 (en) 2013-11-01 2017-09-14 Boehringer Ingelheim Animal Health USA Inc. Antiparasitic and pesticidal isoxazoline compounds
CA2949511A1 (en) 2014-05-19 2015-11-26 Merial, Inc. Anthelmintic compounds
EP3211998B1 (en) 2014-10-31 2021-04-07 Boehringer Ingelheim Animal Health USA Inc. Parasiticidal composition comprising fipronil
UY37137A (es) 2016-02-24 2017-09-29 Merial Inc Compuestos antiparasitarios de isoxazolina, formulaciones inyectables de acción prolongada que los comprenden, métodos y usos de los mismos
SG11201808756XA (en) 2016-04-06 2018-11-29 Merial Inc Process for the preparation of isoxazoline compounds
CN110381738B (zh) 2016-10-14 2021-07-16 勃林格殷格翰动物保健美国公司 农药的和杀寄生物的乙烯基异噁唑啉化合物
CA3059114A1 (en) * 2017-04-05 2018-10-11 Boehringer Ingelheim Animal Health USA Inc. Crystalline forms of (s)-afoxolaner
JP2020530850A (ja) 2017-08-14 2020-10-29 ベーリンガー インゲルハイム アニマル ヘルス ユーエスエイ インコーポレイテッド 殺有害生物および殺寄生生物ピラゾール−イソキサゾリン化合物
SI3752501T1 (sl) 2018-02-13 2023-08-31 Gilead Sciences, Inc. Inhibitorji pd-1/pd-l1
CA3093130C (en) 2018-04-19 2023-10-17 Gilead Sciences, Inc. Pd-1/pd-l1 inhibitors
JP7242641B2 (ja) * 2018-04-27 2023-03-20 クミアイ化学工業株式会社 ５，５－ジ置換－４，５－ジヒドロイソオキサゾールの製造方法
SI3820572T1 (sl) 2018-07-13 2023-12-29 Gilead Sciences, Inc. Inhibitorji pd-1/pd-l1
JP7158577B2 (ja) 2018-10-24 2022-10-21 ギリアード サイエンシーズ， インコーポレイテッド Ｐｄ－１／ｐｄ－ｌ１阻害剤
BR112022006761A2 (pt) 2019-10-08 2022-06-28 Donaldson Co Inc Camadas de meio filtrante incluindo fibras finas de diâmetro misto
WO2021242923A1 (en) 2020-05-27 2021-12-02 Axial Therapeutics, Inc. Tlr2 modulator compounds, pharmaceutical compositions and uses thereof
CA3200234A1 (en) 2020-11-25 2022-06-02 Daryl C. Drummond Lipid nanoparticles for delivery of nucleic acids, and related methods of use
US20250091998A1 (en) * 2021-08-01 2025-03-20 Zenfold Sustainable Technologies Private Limited A process for the preparation of carbamoyl benzamide phenyl isoxazoline class drug/s and its intermediates
CN115710185B (zh) * 2021-08-23 2024-05-03 中国石油化工股份有限公司 利用金属碳化物催化剂生产甲胺的方法
US12064479B2 (en) 2022-05-25 2024-08-20 Akagera Medicines, Inc. Lipid nanoparticles for delivery of nucleic acids and methods of use thereof
CN116903488B (zh) * 2022-11-25 2023-12-15 济南久隆医药科技有限公司 一种阿福拉纳的合成方法
CN115772091B (zh) * 2023-01-05 2023-06-23 济南久隆医药科技有限公司 一种2-氨基-n-(2,2,2-三氟乙基)乙酰胺的合成方法
CN119899156A (zh) * 2023-10-27 2025-04-29 华北制药集团动物保健品有限责任公司 一种阿福拉纳的制备方法

Family Cites Families (38)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3879532A (en) * 1974-01-18 1975-04-22 Shell Oil Co Control by isoxazoles of endoparasitic nematodes
US4129568A (en) * 1977-05-12 1978-12-12 Monsanto Company 2-[3-Aryl-2-isoxazolin-5-yl]benzoates
US5849736A (en) 1993-11-24 1998-12-15 The Dupont Merck Pharmaceutical Company Isoxazoline and isoxazole fibrinogen receptor antagonists
GB9505651D0 (en) 1995-03-21 1995-05-10 Agrevo Uk Ltd AgrEvo UK Limited
CA2252543C (en) 1996-04-26 2003-01-14 Nippon Soda Co., Ltd. Benzene derivatives substituted by heterocycles and herbicides
AR007292A1 (es) 1996-06-06 1999-10-27 Rohm & Haas Compuestos aromaticos benciloxi sustituidos, una composicion fungicida, un metodo para controlar hongos fitopatogenicos y un metodo para controlarinsectos.
GB2351081A (en) 1999-06-18 2000-12-20 Lilly Forschung Gmbh Pharmaceutically active imidazoline compounds and analogues thereof
DE10114597A1 (de) * 2001-03-23 2002-10-02 Bayer Cropscience Gmbh Arylisoxazolin-Derivate, Verfahren zu ihrer Herstellung und ihre Verwendung als Schädlingsbekämpfungsmittel
WO2004018410A1 (ja) * 2002-08-26 2004-03-04 Nissan Chemical Industries, Ltd. 置換ベンズアニリド化合物及び有害生物防除剤
DE10320782A1 (de) 2003-05-09 2004-11-25 Bayer Cropscience Ag Substituierte Oxyarene
JP2005272452A (ja) 2004-02-23 2005-10-06 Nissan Chem Ind Ltd 置換ベンズアニリド化合物及び有害生物防除剤
CN102558082B (zh) * 2004-03-05 2015-09-30 日产化学工业株式会社 异噁唑啉取代苯甲酰胺化合物的制备中间体
JP2007530598A (ja) 2004-03-26 2007-11-01 サイトカイン・ファーマサイエンシズ・インコーポレーテッド マクロファージ遊走阻害因子の阻害に関する、化合物、組成物、作製プロセス、および使用方法
JP5051340B2 (ja) * 2005-06-06 2012-10-17 日産化学工業株式会社 置換イソキサゾリン化合物及び有害生物防除剤
MY146795A (en) 2005-06-09 2012-09-28 Novartis Ag Process for the synthesis of organic compounds
GB0514071D0 (en) 2005-07-07 2005-08-17 Zealand Pharma As N- or C- terminally modified small peptides
KR100546831B1 (ko) 2005-08-31 2006-01-25 (주) 마이크로프랜드 프로브 카드의 탐침팁 공정 방법
ES2443690T3 (es) * 2005-09-02 2014-02-20 Nissan Chemical Industries, Ltd. Compuesto de benzamida sustituido con isoxazolina y agente controlador de organismos dañinos
JP2007106756A (ja) 2005-09-14 2007-04-26 Nissan Chem Ind Ltd 置換イソキサゾリン化合物及び有害生物防除剤
TWI266597B (en) * 2005-09-27 2006-11-11 Delta Electronics Inc Electronic apparatus capable of dissipating heat uniformly
US20090143410A1 (en) * 2005-12-14 2009-06-04 Kanu Maganbhai Patel Isoxazolines for Controlling Invertebrate Pests
TW200803740A (en) * 2005-12-16 2008-01-16 Du Pont 5-aryl isoxazolines for controlling invertebrate pests
CN101346336B (zh) 2005-12-26 2013-02-27 日产化学工业株式会社 1,3-二(取代苯基)-3-取代-2-丙烯-1-酮化合物和其盐
TWI412322B (zh) 2005-12-30 2013-10-21 Du Pont 控制無脊椎害蟲之異唑啉
BRPI0707091B8 (pt) * 2006-03-10 2018-02-14 Nissan Chemical Ind Ltd composto de isoxalina e benzaldoxima substituído ou um sal do mesmo; pesticida, agroquímico, endo- ou ecto-parasiticidapara mamíferos ou pássaros, inseticida e acaricida contendo como um ou mais ingredientes ativos selecionados a partir do composto de isoxalina substituído e o sal do mesmo
BRPI0710403A2 (pt) 2006-04-20 2011-08-09 Du Pont composto composição, composição de controle, de pulverização, de isca, dispositivo de armadilha, métodos de controle, métodos de proteção, semente tratada, composição de proteção
WO2007125984A1 (ja) 2006-04-28 2007-11-08 Nihon Nohyaku Co., Ltd. イソキサゾリン誘導体及び有害生物防除剤並びにその使用方法
JP2008044880A (ja) 2006-08-15 2008-02-28 Bayer Cropscience Ag 殺虫性イソオキサゾリン類
EP2151437A4 (en) 2007-03-07 2012-05-02 Nissan Chemical Ind Ltd ISOXAZOLINE SUBSTITUTED BENZAMIDE COMPOUND AND PEST CONTROL AGENT
WO2008122375A2 (en) * 2007-04-10 2008-10-16 Bayer Cropscience Ag Insecticidal aryl isoxazoline derivatives
CN101815706A (zh) * 2007-06-13 2010-08-25 杜邦公司 异*唑啉杀昆虫剂
TWI430995B (zh) 2007-06-26 2014-03-21 Du Pont 萘異唑啉無脊椎有害動物控制劑
MX368680B (es) * 2007-06-27 2019-10-11 Du Pont Administración subcutánea de un derivado de isoxazol-benzamida para usarse en un método para proteger un mamífero de una pulga.
US8952175B2 (en) * 2007-06-27 2015-02-10 Nissan Chemical Industries, Ltd. Method for production of 3-hydroxypropan-1-one compound, method for production of 2-propen-1-one compound and method for production of isoxazoline compound
TWI556741B (zh) 2007-08-17 2016-11-11 英特威特國際股份有限公司 異唑啉組成物及其作為抗寄生蟲藥上的應用
TWI600639B (zh) * 2007-08-17 2017-10-01 杜邦股份有限公司 製備５-鹵烷基-４，５-二氫異唑衍生物之化合物
US8318757B2 (en) 2007-09-10 2012-11-27 Nissan Chemical Industries, Ltd. Substituted isoxazoline compound and pest control agent
MX2010003557A (es) 2007-10-03 2010-04-12 Du Pont Compuestos de isoxazolina de naftaleno para el control de plagas de invertebrados.

Also Published As

Publication number Publication date
TWI461411B (zh) 2014-11-21
US8513431B2 (en) 2013-08-20
JP2014221775A (ja) 2014-11-27
CO6260136A2 (es) 2011-03-22
ZA201000214B (en) 2011-03-30
WO2009025983A3 (en) 2009-05-07
TW200914429A (en) 2009-04-01
KR20100044892A (ko) 2010-04-30
KR101597839B1 (ko) 2016-02-25
MX337588B (es) 2016-03-11
PT2176244T (pt) 2016-07-27
MY176115A (en) 2020-07-24
US20100249424A1 (en) 2010-09-30
WO2009025983A4 (en) 2009-06-25
IL203174A (en) 2014-08-31
US20120277442A1 (en) 2012-11-01
MX2010001773A (es) 2010-03-10
RU2010109881A (ru) 2011-09-27
US8217180B2 (en) 2012-07-10
AR067948A1 (es) 2009-10-28
JP5965102B2 (ja) 2016-08-03
TWI649303B (zh) 2019-02-01
US20130165663A9 (en) 2013-06-27
TW201434808A (zh) 2014-09-16
CN101855215A (zh) 2010-10-06
BRPI0814153A2 (pt) 2015-01-06
CA2693067A1 (en) 2009-02-26
KR20150082693A (ko) 2015-07-15
EP2176244A2 (en) 2010-04-21
AU2008289321A1 (en) 2009-02-26
MY150980A (en) 2014-03-31
TWI600639B (zh) 2017-10-01
BRPI0814153B1 (pt) 2018-08-21
HK1143373A1 (zh) 2010-12-31
RU2536039C2 (ru) 2014-12-20
JP2010536767A (ja) 2010-12-02
WO2009025983A2 (en) 2009-02-26
ES2587386T3 (es) 2016-10-24
TW201718454A (zh) 2017-06-01
CN105693646A (zh) 2016-06-22
EP2176244B1 (en) 2016-06-01
AU2008289321B2 (en) 2014-02-20
BRPI0814153B8 (pt) 2022-12-06

Similar Documents

Publication Publication Date Title
CA2693067C (en) Method for preparing 5-haloalkyl-4,5-dihydroisoxazole derivatives
CA2718668C (en) Method for preparing 3-trifluoromethyl chalcones
HK1143373B (en) Method for preparing 5-haloalkyl-4,5-dihydroisoxazole derivatives
HK1195765B (en) 1-chloro-3-iodo-5-(trifluoromethyl)benzene
HK1195765A (en) 1-chloro-3-iodo-5-(trifluoromethyl)benzene

Legal Events

Date Code Title Description
EEER Examination request

Effective date: 20130802

EEER Examination request

Effective date: 20130802