Nissan Chemical Industries Limited

Nissan Chemical Corporation

Manabu Yaosaka

Takeshi Mita

Mitsuaki Komoda

Takashi Mizukoshi

Takamasa Kikuchi

Kazutaka Matoba

Yuji Moriyama

Eitatsu Ikeda

Ken-ichi Toyama

Yuki Furukawa

Shinji Takii

Yoshihide Masuzawa

Tomohiro Matsumoto

Tomohisa Utsunomiya

Hiroyuki Kousaka

Shunsuke Fukuya

Yasuhiro Sakurai

Ken-Ichi Toyama

A substituted alkenylbenzene compound of formula (4): wherein Xis selected from the group consisting of a halogen atom, &#x2014;SF, C-Chaloalkyl, hydroxy C-Chaloalkyl, C-Calkoxy C-Chaloalkyl, C-Chalocycloalkyl, C-Chaloalkoxy, C-Chaloalkoxy C-Chaloalkoxy, C-Chaloalkylthio, C-Chaloalkylsulfinyl and C-Chaloalkylsulfonyl; Xis selected from the group consisting of a hydrogen atom, halogen atom, cyano, nitro, C-Calkyl, C-Chaloalkyl, C-Calkoxy and C-Calkylthio; Xis selected from the group consisting of a hydrogen atom, halogen atom, cyano, C-Calkyl, C-Calkoxy and C-Chaloalkoxy; Ris &#x2014;C(R)(R)R, where Rand Rindependently of each other are a halogen atom, or Rand Rtogether form 3- to 6-membered ring together with the carbon atom bonding them by forming a C-Chaloalkylene chain, and Ris selected from the group consisting of a hydrogen atom, halogen atom, C-Calkyl, C-Chaloalkyl, C-Chaloalkoxy and C-Chaloalkylthio, with a proviso that in case where Xis a fluorine atom, chlorine atom or trifluoromethyl, and both Xand Xare a hydrogen atom, in case where both Xand Xare fluorine atom and Xis a hydrogen atom, and in case where both Xand Xare trifluoromethyl and Xis a hydrogen atom, Ris a hydrogen atom, chlorine atom, bromine atom, iodine atom, C-Calkyl, C-Chaloalkyl, C-Chaloalkoxy or C-Chaloalkylthio.

Isoxazoline-substituted benzamide compound and pesticide

A substituted alkenylbenzene compound of formula (4): wherein Xis selected from the group consisting of a halogen atom, &#x2014;SF, C-Chaloalkyl, hydroxy C-Chaloalkyl, C-Calkoxy C-Chaloalkyl, C-Chalocycloalkyl, C-Chaloalkoxy, C-Chaloalkoxy C-Chaloalkoxy, C-Chaloalkylthio, C-Chaloalkylsulfinyl and C-Chaloalkylsulfonyl; Xis selected from the group consisting of a hydrogen atom, halogen atom, cyano, nitro, C-Calkyl, C-Chaloalkyl, C-Calkoxy and C-Calkylthio; Xis selected from the group consisting of a hydrogen atom, halogen atom, cyano, C-Calkoxy and C-Chaloalkoxy; Ris &#x2014;C(R)(R)R, where Rand Rindependently of each other are a halogen atom, or Rand Rtogether form 3- to 6-membered ring together with the carbon atom bonding them by forming a C-Chaloalkylene chain, and Ris selected from the group consisting of a hydrogen atom, halogen atom, C-Chaloalkyl, C-Chaloalkoxy and C-Chaloalkylthio, with a proviso that in case where Xis a fluorine atom, chlorine atom or trifluoromethyl, and both Xand Xare a hydrogen atom, in case where both Xand Xare fluorine atom and Xis a hydrogen atom, and in case where both Xand Xare trifluoromethyl and Xis a hydrogen atom, Ris a hydrogen atom, chlorine atom, bromine atom, iodine atom, C-Calkyl, C-Chaloalkyl, C-Chaloalkoxy or C-Chaloalkylthio.

A substituted alkenylbenzene compound of formula (4): wherein Xis selected from the group consisting of halogen atom, &#x2014;SF, C-Chalo alkyl, hydroxy C-Chaloalkyl, C-Calkoxy C-Chaloalkyl, C-Chalocycloalkyl, C-Chaloalkoxy, C-Chaloalkoxy C-Chaloalkoxy, C-Chaloalkylthio, C-Chaloalkylsulfinyl and C-Chaloalkylsulfonyl; Xis selected from the group consisting of a hydrogen atom, halogen atom, cyano, nitro, C-Calkyl, C-Chaloalkyl, C-Calkoxy and C-Calkylthio; Xis selected from the group consisting of a hydrogen atom, halogen atom, cyano, C-Calkyl, C-Calkoxy and C-Chaloalkoxy; Ris &#x2014;C(R)(R)R, where Rand Rindependently of each other are a halogen atom, or Rand Rtogether form 3- to 6-membered ring together with the carbon atom bonding them by forming a C-Chaloalkylene chain, and Ris selected from the group consisting of a hydrogen atom, halogen atom, C-Calkyl, C-Chaloalkyl, C-Chaloalkoxy and C-Chaloalkylthio, with a proviso that in case where Xis a fluorine atom, chlorine atom or trifluoromethyl, and both Xand Xare a hydrogen atom, in case where both Xand Xare fluorine atom and Xis a hydrogen atom, and in case where both Xand Xare trifluoromethyl and Xis a hydrogen atom, Ris a hydrogen atom, chlorine atom, bromine atom, iodine atom, C-Calkyl, C-Chaloalkyl, C-Chaloalkoxy or C-Chaloalkylthio.

There is provided a novel intermediate for producing pesticides. A method for producing the compound of Formula (3) comprises reacting an aromatic ketone compound of Formula (4) and a substituted acetophenone compound of Formula (5) as starting raw materials in an organic solvent or water in the presence or absence of an additive in the presence of a base in a suspended state. A method may comprise dehydrating the compound of Formula (3). A method for producing compound (2) in one step comprises reacting compound (4) and compound (5) to obtain compound (3). Further, a method for producing an isoxazoline compound of Formula (1) comprises reacting compound (2) and a hydroxylamine in an aliphatic or an aromatic hydrocarbon solvent which is optionally substituted by a halogen atom by adding an additive selected from a phase-transfer catalyst, a C-Calcohol and an aprotic polar solvent in the presence of a base and water.

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

There is provided a method for catalytic asymmetric synthesis of optically active isoxazoline compound and an optically active isoxazoline compound. A method for catalytic asymmetric synthesis of optically active isoxazoline compound of a formula (6) including reacting an &#x3b1;,&#x3b2;-unsaturated carbonyl compound of a formula (1) and a hydroxylamine in a solvent in the presence of a base by adding a chiral phase transfer catalyst. An optically active isoxazoline compound of a formula (13) that can be synthesized by the method. 

Method for catalytic asymmetric synthesis of optically active isoxazoline compound and optically active isoxazoline compound

An isoxazoline-substituted benzamide compound of formula (1) or a salt thereof: wherein A, Aand Aindependently of one another are carbon atom or nitrogen atom, G is benzene ring, etc., W is oxygen atom or sulfur atom, etc., X is halogen atom, C-Chaloalkyl, etc., Y is halogen atom, C-Calkyl, etc., Ris &#x2014;CH&#x2550;NOR, &#x2014;C(O)OR, &#x2014;C(O)NHR, phenyl substituted with (Z), D-14, D-52, D-53, D-55 to D-59, etc., Ris C-Calkyl, etc., Ris C-Calkyl, etc., Ris hydrogen atom, &#x2014;C(O)R, &#x2014;C(O)OR, etc., Ris C-Calkyl, &#x2014;CHR, C-Calkynyl, &#x2014;C(O)R, &#x2014;C(O)OR, etc., further when Ris &#x2014;CH&#x2550;NOR, &#x2014;C(O)ORor &#x2014;C(O)N(R)R, Rmay be hydrogen atom, Ris C-Chaloalkyl, etc., Ris cyano, &#x2014;OR, etc., Ris C-Calkyl, C-Chaloalkyl, C-Calkoxy C-Calkyl, C-Calkylthio C-Calkyl, C-Ccycloalkyl, C-Calkenyl, etc., Ris C-Calkyl, C-Chaloalkyl, &#x2014;C(O)Ror &#x2014;C(O)OR, etc., Ris C-Calkyl or C-Ccycloalkyl, etc., Z is halogen atom, cyano, nitro, C-Calkyl, C-Calkoxy, etc., m is an integer of 0 to 5, n is an integer of 0 to 4, p1 is an integer of 1 to 5. The pesticide containing these compounds.

There is provided a novel intermediate for producing pesticides. A method for producing the compound of Formula (3) comprises reacting an aromatic ketone compound of Formula (4) and a substituted acetophenone compound of Formula (5) as starting raw materials in an organic solvent or water in the presence or absence of an additive in the presence of a base in a suspended state. A method may comprise dehydrating the compound of Formula (3). A method for producing compound (2) in one step comprises reacting compound (4) and compound (5) to obtain compound (3). Further, a method for producing an isoxazoline compound of Formula (1) comprises reacting compound (2) and a hydroxylamine in an aliphatic or an aromatic hydrocarbon solvent which is optionally substituted by a halogen atom by adding an additive selected from a phase-transfer catalyst, a C-Calcohol and an aprotic polar solvent in the presence of a base and water. 

A substituted alkenylbenzene compound of formula (4): 

A substituted alkenylbenzene compound of formula (4): wherein Xis a halogen atom, &#x2014;SF, C-Chaloalkyl, hydroxy C-Chaloalkyl, C-Calkoxy C-Chaloalkyl, C-Chalocycloalkyl, C-Chaloalkoxy, C-Chaloalkoxy C-Chaloalkoxy, C-Chaloalkylthio, C-Chaloalkylsulfinyl or C-Chaloalkylsulfonyl; Xis a hydrogen, halogen, cyano, nitro, C-Calkyl, C-Chaloalkyl, C-Calkoxy or C-Calkylthio; Xis a hydrogen, halogen, cyano, C-Calkyl, C-Calkoxy or C-Chaloalkoxy; Ris &#x2014;C(R)(R)R, where Rand Rare a halogen, or Rand Rtogether form a- to-membered ring together with the carbon bonding them by forming a C-Chaloalkylene chain, and Ris a hydrogen, halogen, C-Calkyl, C-Chaloalkyl, C-Chaloalkoxy or C-Chaloalkylthio, with a proviso that where Xis a fluorine, chlorine or trifluoromethyl, and Xand Xare hydrogen, where Xand Xare fluorine and Xis a hydrogen, or where Xand Xare trifluoromethyl and Xis a hydrogen, Ris a hydrogen, chlorine, bromine, iodine, C-Calkyl, C-Chaloalkyl, C-Chaloalkoxy or C-Chaloalkylthio.

A production method of an isoxazoline-substituted benzoic acid amide compound of Formula (1) where X is a halogen atom, Chaloalkyl, etc., Y is a halogen atom, Calkyl, etc., Ris a Chaloalkyl, etc., Rand Rindependently of each other are a hydrogen atom, Calkyl, etc., Ris Calkyl, Chaloalkyl, etc., Ris a hydrogen atom, calkyl, etc., m is an integer of 0 to 5, n is an integer of 0 to 4, including: reacting an isoxazoline-substituted benzene compound of Formula (3) where X, Y, R, m, and n are the same as defined above, L is a chlorine atom, a bromine atom, &#x2014;C(O)OH, &#x2014;C(O)J, etc., J is a halogen atom, with a 2-aminoacetic acid amide compound of Formula (2) where R, R, R, and Rare the same as defined above, or a salt thereof; crystal forms and the production method thereof. 

Production method of isoxazoline-substituted benzoic acid amide compound

A 3,5-Bis (substituted aryl) substituted isoxazoline compound of formula (2) or a salt thereof: wherein A1 is a carbon atom or nitrogen atom; X1 is selected from the group consisting of a halogen atom, &#x2014;SF5, C1-C6haloalkyl, hydroxy C1-C6haloalkyl, C1-C6alkoxy C1-C6haloalkyl, C1-C6haloalkoxy C1-C6haloalkyl, C3-C8halocycloalkyl, C1-C6haloalkoxy, C1-C3haloalkoxy C1-C3haloalkoxy, C1-C6haloalkylthio, C1-C6haloalkylsulfinyl and C1-C6haloalkylsulfonyl; X2 is selected from the group consisting of a halogen atom, cyano, nitro, C1-C6alkyl, C1-C6haloalkyl, &#x2014;OR5, &#x2014;OSO2R5 and &#x2014;S(O)rR5; Y is selected from the group consisting of a halogen atom, cyano, nitro, C1-C4alkyl, C1-C4haloalkyl, C1-C4alkoxy, C1-C4haloalkoxy, C1-C6alkylthio, C1-C6haloalkylthio, C1-C6alkylsulfonyl, C1-C6haloalkylsulfonyl, &#x2014;NHR7 and &#x2014;N(R7)R6; R is selected from the group consisting of a halogen atom, cyano, nitro, &#x2014;NH2, halosulfonyloxy, C1-C6alkylsulfonyloxy, C1-C6haloalkylsulfonyloxy, phenylsulfonyloxy, phenylsulfonyloxy substituted with (Z)p1 and &#x2014;C(O)Ra; m1 is an integer of 0 to 2; n is an integer of 0 or 1; p1 is an integer of 1 to 5; and r is an integer of 0 to 2.

An isoxazoline-substituted benzamide compound of formula (1) or a salt thereof: wherein A, Aand Aindependently of one another are carbon atom or nitrogen atom, G is benzene ring, etc., X is halogen atom, C-Chaloalkyl, etc., Y is halogen atm, C-Calkyl, etc., Ris C-Calkyl arbitrarily substituted with R, C-Calkenyl, arbitrarily substituted with Ris oxygen atom or sulfur atom, &#x2014;N(R)R, etc., Ris hydrogen atom, C-Calkoxy C-Calkyl, etc., Ris C-Chaloalkyl, etc., Ris halogen atom, cyano, phenyl substituted with (Z), D-1 to D-60, E-1 to E-49, etc., Ris phenyl, phenyl substituted with (Z), etc., Ris hydrogen atom, C-Calkyl, etc., Z is halogen atom, nitro, C-Calkoxy, etc., D-1 to D-60 are 5- or 6-membered aromatic heterocyclic rings, E-1 to E-49 are 5- or 6-membered saturated heterocyclic rings, m is an integer of 0 to 5, n is an integer of 0 to 4, p1 is an integer of 1 to 5. The pesticide containing these compounds.

An isoxazoline-substituted benzamide compound of formula (1) or a salt thereof: wherein A, Aand Aindependently of one another are carbon atom or nitrogen atom, G is benzene ring, etc., W is oxygen atom or sulfur atom, etc., X is halogen atom, C-Chaloalkyl, etc., Y is halogen atm, C-Calkyl, etc., Ris &#x2014;CH&#x2550;NOR, &#x2014;C(O)OR, &#x2014;C(O)NHR, phenyl substituted with (Z), D-14, D-52, D-53, D-55 to D-59, etc., Ris C-Calkyl, etc., Ris C-Calkyl, etc., Ris hydrogen atom, &#x2014;C(O)R, &#x2014;C(O)OR, etc., Ris C-Calkyl, &#x2014;CHR, C-Calkynyl, &#x2014;C(O)R, &#x2014;C(O)OR, etc., further when Ris &#x2014;CH&#x2550;NOR, &#x2014;C(O)ORor &#x2014;C(O)N(R)R, Rmay be hydrogen atom, Ris C-Chaloalkyl, etc., Ris cyano, &#x2014;OR, etc., Ris C-Calkyl, C-Chaloalkyl, C-Calkoxy C-Calkyl, C-Calkylthio C-Calkyl, C-Ccycloalkyl, C-Calkenyl, etc., Ris C-Calkyl, C-Chaloalkyl, &#x2014;C(O)Ror &#x2014;C(O)OR, etc., Ris C-Calkyl or C-Ccycloalkyl, etc., Z is halogen atom, cyano, nitro, C-Calkyl, C-Calkoxy, etc., m is an integer of 0 to 5, n is an integer of 0 to 4, p1 is an integer of 1 to 5. The pesticide containing these compounds.

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Funabashi, Japan

Manabu Yaosaka