Process for producing anthranilamide compound
AssigneeIshihara Sangyo Kaisha, Ltd.
InventorsToru Koyanagi, Kazuhiro Yamamoto, Tetsuo Yoneda, Shigehisa Kanbayashi, Toyoshi Tanimura, Yohei Taguchi, Tatsunori Yoshida
Life of this patent
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Abstract
To provide a process for producing a specific anthranilamide compound or its salt. To provide a process for producing an anthranilamide compound represented by the formula (I) or its salt: wherein each of R1a and R3 which are independent of each other, is halogen or haloalkyl; R2 is cyclopropyl alkyl or cyclobutyl alkyl; and Hal is a chlorine atom or a bromine atom, which comprises a step of selectively halogenating a compound represented by the formula (II): wherein R1a, R2 and R3 are as defined above.
Claims13
A process for producing an anthranilamide compound represented by the formula (I) or its salt:
- wherein each of R1a and R3 which are independent of each other, is halogen or haloalkyl;
- R2 is cyclopropyl alkyl or cyclobutyl alkyl;
- and Hal is a chlorine atom or a bromine atom, which comprises reacting a compound represented by the formula (II):
- wherein R1a, R2 and R3 are as defined above, with a halogenating agent.
A process for producing an anthranilamide compound represented by the formula (I-1) or its salt:
- wherein R1a is halogen or haloalkyl;
- R2 is cyclopropyl alkyl or cyclobutyl alkyl;
- and Hal is a chlorine atom or a bromine atom, which comprises reacting a compound represented by the formula (II-1):
- wherein R1a and R2 are as defined above, with a halogenating agent.
A process for producing a compound represented by the formula (II-1):
- wherein R1a is halogen or haloalkyl;
- and R2 is cyclopropyl alkyl or cyclobutyl alkyl, which comprises reacting a compound represented by the formula (VI-1):
- wherein R1a and R2 are as defined above, with a compound represented by the formula (VII):
- wherein X is a chlorine atom or a bromine atom to produce a compound represented by the formula (VIII-1):
- wherein R1a and R2 are as defined above, reacting the obtained compound of the formula (VIII-1) with a sulfonyl chloride, a chlorinating agent or an acid chloride to produce a compound represented by the formula (IX-1):
- wherein L is alkylsulfonyloxy, alkoxycarbonyloxy, alkylcarbonyloxy, phenylsulfonyloxy, p-toluenesulfonyloxy or a chlorine atom;
- and R1a and R2 are as defined above, reacting the obtained compound of the formula (IX-1) with a brominating agent to produce a compound represented by the formula (III-1):
- wherein R1a and R2 are as defined above, and reacting the obtained compound of the formula (III-1) with an oxidizing agent.
A compound represented by the formula (II-1) or its salt:
- wherein R1a is halogen or haloalkyl, and R2 is cyclopropyl alkyl or cyclobutyl alkyl.
A compound represented by the formula (V-1) or its salt:
- wherein R1a is halogen or haloalkyl, and R2 is cyclopropyl alkyl or cyclobutyl alkyl.
A compound represented by the formula (VI-1) or its salt:
- wherein R1a is halogen or haloalkyl, and R2 is cyclopropyl alkyl or cyclobutyl alkyl.
A compound represented by the formula (VIII-1) or its salt:
- wherein R1a is halogen or haloalkyl, and R2 is cyclopropyl alkyl or cyclobutyl alkyl.
A compound represented by the formula (IX-1) or its salt:
- wherein R1a is halogen or haloalkyl;
- R2 is cyclopropyl alkyl or cyclobutyl alkyl;
- and L is alkylsulfonyloxy, alkoxycarbonyloxy, alkylcarbonyloxy, phenylsulfonyloxy, p-toluenesulfonyloxy or a chlorine atom.
A compound represented by the formula (III-1) or its salt:
- wherein R1a is halogen or haloalkyl, and R2 is cyclopropyl alkyl or cyclobutyl alkyl.
A compound represented by the formula (X-1) or its salt:
- wherein R1a is halogen or haloalkyl, R2 is cyclopropyl alkyl or cyclobutyl alkyl, and R5 is alkyl.
A compound represented by the formula (XI-1) or its salt:
- wherein R1a is halogen or haloalkyl, and R5 is alkyl.
Dependencies are inferred from the claim text.