公开(公告)号：EP0834497B1

公开(公告)日：2001-10-24

申请号：EP96918834.1

申请日：1996-06-19

申请人： SAGAMI CHEMICAL RESEARCH CENTER ,  Iharanikkei Chemical Industry Co., Ltd.

发明人： HIRAI, Kenji ,  MASUDA, Katsuyuki ,  TAKAO, Yoshihiro ,  SUGIYAMA, Masahide ,  ONO, Yukio ,  MATSUZAWA, Masahumi

IPC分类号： C07C69/65 ,  C07C67/30 ,  C07D311/76 ,  C07C67/307

CPC分类号： C07D311/76 ,  C07C67/24 ,  C07C69/65

摘要： A process for efficiently and conveniently producing 2-(halomethyl)phenylacetic acid esters (3), which are useful as intermediates in the production of agricultural insecticides, by reacting a 3-isochromanone derivative (1) with a hydrogen halide and an alcohol or a dihalomethyl alkyl ether followed by the reaction with an alcohol (2) in the presence of a base. The starting 3-isochromanone derivative (1) can be produced in a high yield by reacting an α,α'-o-xylylene dihalide derivative (4) with carbon monoxide and water in the presence of a palladium catalyst and an inorganic base in an organic solvent and subsequently treating with an acid.

公开(公告)号：EP0834497A1

公开(公告)日：1998-04-08

申请号：EP96918834.1

申请日：1996-06-19

申请人： SAGAMI CHEMICAL RESEARCH CENTER ,  Iharanikkei Chemical Industry Co., Ltd.

发明人： HIRAI, Kenji ,  MASUDA, Katsuyuki ,  TAKAO, Yoshihiro ,  SUGIYAMA, Masahide ,  ONO, Yukio ,  MATSUZAWA, Masahumi

IPC分类号： C07C69/65 ,  C07C67/30 ,  C07D311/76

CPC分类号： C07D311/76 ,  C07C67/24 ,  C07C69/65

摘要： 2-(Halomethyl)phenylacetic acid esters (3) which are useful as intermediates for producing agricultural fungicides are produced efficiently and conveniently by reacting a 3-isochromanone derivative (1) with a hydrogen halide and an alcohol or reacting (1) with a halomethyl alkyl ether and then reacting the product with an alcohol in the presence of a base. The starting compound, 3-isochromanone (1), is produced in good yield by reacting an α,α'-o-xylene dihalide (4) with carbon monoxide and water in an organic solvent in the presence of a palladium catalyst and an inorganic base and then treating the product with an acid.

公开(公告)号：EP0812834B1

公开(公告)日：2001-06-20

申请号：EP96903234.1

申请日：1996-02-26

申请人： SAGAMI CHEMICAL RESEARCH CENTER ,  KAKEN PHARMACEUTICAL CO., LTD.

发明人： HIRAI, Kenji ,  MASUDA, Katsuyuki ,  YANO, Tomoyuki ,  OHNO, Ryuta ,  MATUKAWA, Tomoko ,  IMAI, Kiyomi ,  OKANO, Natsuko ,  YOSHII, Tomoko ,  MOURI, Takehito

IPC分类号： C07D263/44 ,  C07C67/31 ,  C07C69/708 ,  B01J27/128 ,  B01J27/138 ,  B01J31/04 ,  B01J31/18 ,  C07B61/00

CPC分类号： C07D263/44 ,  C07C67/31 ,  C07C69/708

摘要： An industrial process for efficiently preparing a 3-(substituted phenyl)-5-isopropylidene-1,3-oxazolidine-2,4-dione derivative having a potent herbicidal activity without using phosgene or the like. More precisely, a process for preparing a 3-(substituted phenyl)-5-alkylidene-1,3-oxazolidine-2,3-dione derivative of general formula (III) by reacting an N-(substituted phenyl)carbamate of general formula (I) with a 2-hydroxy-3-alkenoate of general formula (II) or a 3-alkoxy-2-hydroxyalkanoate of general formula (IV), wherein Ar is substituted phenyl; R1 is C1-C6 alkyl; R?2 and R3¿ are each independently hydrogen or C¿1?-C12 alkyl; and R?4 and R5¿ are each independently C¿1?-C6 alkyl.

公开(公告)号：EP0812834A1

公开(公告)日：1997-12-17

申请号：EP96903234.1

申请日：1996-02-26

申请人： SAGAMI CHEMICAL RESEARCH CENTER ,  KAKEN PHARMACEUTICAL CO., LTD.

发明人： HIRAI, Kenji ,  MASUDA, Katsuyuki ,  YANO, Tomoyuki ,  OHNO, Ryuta ,  MATUKAWA, Tomoko ,  IMAI, Kiyomi ,  OKANO, Natsuko ,  YOSHII, Tomoko ,  MOURI, Takehito

IPC分类号： C07D263/44 ,  C07C67/31 ,  C07C69/708 ,  B01J27/128 ,  B01J27/138 ,  B01J31/04 ,  B01J31/18 ,  C07B61/00

CPC分类号： C07D263/44 ,  C07C67/31 ,  C07C69/708

摘要： The present invention provides an industrial process for efficiently preparing a 3-(substituted phenyl)-5-isopropylidene-1,3-oxazolidine-2,4-dione derivative having a potent herbicidal activity without using phosgene or the like. The present invention relates to a process for preparing a 3-(substituted phenyl)-5-alkylidene-1,3-oxazolidine-2,4-dione derivative represented by general formula (III), which comprises reaction of an N-(substituted phenyl)carbamate represented by general formula (I) with a 2-hydroxy-3-alkenoate represented by general formula (II) or with a 3-alkoxy-2-hydroxyalkanoate represented by general formula (IV):
(wherein Ar is a substituted phenyl group, R 1 is an alkyl group having a carbon number of from 1 to 6, R 2 and R 3 are independently hydrogen atoms or alkyl groups having carbon numbers of from 1 to 12, and R 4 and R 5 are independently alkyl groups having carbon numbers of from 1 to 6).

摘要翻译： 本发明提供了在不使用光气等的情况下有效制备具有强效除草活性的3-（取代苯基）-5-异亚丙基-1,3-恶唑烷-2,4-二酮衍生物的工业方法。 本发明涉及一种制备由通式（III）表示的3-（取代苯基）-5-亚烷基-1,3-恶唑烷-2,4-二酮衍生物的方法，该方法包括N-（取代的 苯基）氨基甲酸酯与由通式（II）表示的2-羟基-3-烯酸酯或由通式（IV）表示的3-烷氧基-2-羟基链烷酸酯组成的化合物：其中Ar 是取代的苯基，R 1是碳数为1至6的烷基，R 2和R 3独立地为氢原子或碳数为1至12的烷基，以及 R 4和R 5独立地为碳数为1至6的烷基）。

公开(公告)号：EP0722939A1

公开(公告)日：1996-07-24

申请号：EP94929018.3

申请日：1994-10-07

申请人： SAGAMI CHEMICAL RESEARCH CENTER ,  KAKEN PHARMACEUTICAL CO., LTD.

发明人： HIRAI, Kenji ,  MATSUKAWA, Tomoko ,  YANO, Tomoyuki ,  MASUDA, Katsuyuki ,  YOSHII, Tomoko ,  MOURI, Takehito ,  UGAI, Sadayuki ,  YAMADA, Osamu

IPC分类号： C07D263/48 ,  A01N43/76

CPC分类号： C07D263/48 ,  A01N43/76

摘要： The invention relates to 4-imino-oxazolidine-2-one derivatives represented by the general formula (1):

and a process for producing said compounds by reacting aryl isocyanates of the general formula (2):

with methacrolein cyanohydrin in the presence of a base, as well as a herbicide containing said compounds as an active ingredient; it also relates to a process for producing oxazolidinedione derivatives useful as herbicides by hydrolyzing said compounds.

摘要翻译： 本发明涉及4-亚氨基恶唑烷-2-酮衍生物由通式（1）表示：以及用于通过使通式（2）的芳基异氰酸酯生产所述化合物的方法：用异丁烯醛 在碱，以及除草化合物的存在氰醇含有所述作为活性成分; 因此，它涉及一种生产作为通过水解所述化合物的除草剂有用恶唑烷二酮衍生物的方法。