Phthalamide derivatives, or salt thereof agrohorticultural insecticide, and method for using the same

Information

  • Patent Grant
  • 6603044
  • Patent Number
    6,603,044
  • Date Filed
    Monday, November 29, 1999
    25 years ago
  • Date Issued
    Tuesday, August 5, 2003
    21 years ago
Abstract
The present invention provides a phthalamide derivative of the formula (I): wherein A1 is (substituted) C1-C8 alkylene, (substituted) C3-C8 alkenylene, (substituted) C3-C8 alkynylene, etc., R1 is H, (halo) C3-C6 cycloalkyl, (substituted) phenyl, (substituted) heterocycle, —A2—R4, etc., R2 and R3 are H, C3-C6 cycloalkyl, —A2—R4, etc., A2 is —C(═O)—, —C(═S)— or —C(═NR5)—, R4 is H, alkyl, (substituted) phenyl, (substituted) heterocycle, etc., X and Y are halogen, cyano, nitro, (halo) C1-C6 alkyl, (halo) C1-C6 alkoxy, etc., l is 0-4, m is 0-5, n is 0-2; and an agrohorticultural insecticide containing said compound as active ingredient and exhibiting an excellent insecticidal effect.
Description




BACKGROUND OF THE INVENTION




1. Field of the Invention




The present invention relates to a phthalamide derivative or salt thereof, an agrohorticultural insecticide containing said compound as an active ingredient thereof, and a method for using the agrohorticultural agent.




2. Related Art




JP-A-61-180753 discloses some of the phthalamide derivatives of the present invention. However, in that patent application specification, there is neither disclosed nor suggested about usefulness of said derivatives as an agrohorticultural insecticide. Further, although similar compounds are disclosed in JP-A-59-163353 and J. C. S. Perkin I, 1338-1350 (1978), etc., there is made no mention nor suggestion in these publications about usefulness of those compounds as an agrohorticultural insecticide.




SUMMARY OF THE INVENTION




The present inventors have conducted extensive studies with the aim of developing a novel agrohorticultural agent. As a result, it has been found that the phthalamide derivatives of the present invention represented by general formula (I), which are novel compounds not found in literature, can be put to a novel use as an agrohorticultural insecticide comprising not only these novel compounds but also some known compounds disclosed in prior art. Based on this finding, the present invention has been accomplished.




DETAILED DESCRIPTION OF THE INVENTION




The present invention relates to phthalamide derivatives represented by the following general formula (I) or salt thereof, an agrohorticultural insecticide containing, as active ingredients thereof, the phthalamide derivative represented by the general formula (I) or salt thereof and some known compounds, and a method for using the same:











wherein A


1


represents C


1


-C


8


alkylene group, substituted C


1


-C


8


alkylene group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, halo C


1


-C


6


alkyl group, C


1


-C


6


alkoxy group, halo C


1


-C


6


alkoxy group, C


1


-C


6


alkylthio group, halo C


1


-C


6


alkylthio group, C


1


-C


6


alkylsulfinyl group, halo C


1


-C


6


alkylsulfinyl group, C


1


-C


6


alkylsulfonyl group, halo C


1


-C


6


alkylsulfonyl group, hydroxy C


1


-C


6


alkyl group, C


1


-C


6


alkoxy C


1


-C


6


alkyl group, C


1


-C


6


alkylthio C


1


-C


6


alkyl group, C


1


-C


6


alkoxycarbonyl group, phenyl group and substituted phenyl group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C


1


-C


6


alkyl group, halo C


1


-C


6


alkyl group, C


1


-C


6


alkoxy group, halo C


1


-C


6


alkoxy group, C


1


-C


6


alkylthio group, halo C


1


-C


6


alkylthio group, C


1


-C


6


alkylsulfinyl group, halo C


1


-C


6


alkylsulfinyl group, C


1


-C


6


alkylsulfonyl group, halo C


1


-C


6


alkylsulfonyl group, mono C


1


-C


6


alkylamino group, di C


1


-C


6


alkylamino group in which C


1


-C


6


alkyl groups may be same or different, and C


1


-C


6


alkoxycarbonyl group, C


3


-C


8


alkenylene group, substituted C


3


-C


8


alkenylene group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, halo C


1


-C


6


alkyl group, C


1


-C


6


alkoxy group, halo C


1


-C


6


alkoxy group, C


1


-C


6


alkylthio group, halo C


1


-C


6


alkylthio group, C


1


-C


6


alkylsulfinyl group, halo C


1


-C


6


alkylsulfinyl group, C


1


-C


6


alkylsulfonyl group, halo C


1


-C


6


alkylsulfonyl group, C


1


-C


6


alkylthio C


1


-C


6


alkyl group, C


1


-C


6


alkoxycarbonyl group, phenyl group and substituted phenyl group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C


1


-C


6


alkyl group, halo C


1


-C


6


alkyl group, C


1


-C


6


alkoxy group, halo C


1


-C


6


alkoxy group, C


1


-C


6


alkylthio group, halo C


1


-C


6


alkylthio group, C


1


-C


6


alkylsulfinyl group, halo C


1


-C


6


alkylsulfinyl group, C


1


-C


6


alkylsulfonyl group, halo C


1


-C


6


alkylsulfonyl group, mono C


1


-C


6


alkylamino group, di C


1


-C


6


alkylamino group in which C


1


-C


6


alkyl groups may be same or different, and C


1


-C


6


alkoxycarbonyl group, C


3


-C


8


alkynylene group, or substituted C


3


-C


8


alkynylene group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, halo C


1


-C


6


alkyl group, C


1


-C


6


alkoxy group, halo C


1


-C


6


alkoxy group, C


1


-C


6


alkylthio group, halo C


1


-C


6


alkylthio group, C


1


-C


6


alkylsulfinyl group, halo C


1


-C


6


alkylsulfinyl group, C


1


-C


6


alkylsulfonyl group, halo C


1


-C


6


alkylsulfonyl group, C


1


-C


6


alkylthio C


1


-C


6


alkyl group, C


1


-C


6


alkoxycarbonyl group, phenyl group and substituted phenyl group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C


1


-C


6


alkyl group, halo C


1


-C


6


alkyl group, C


1


-C


6


alkoxy group, halo C


1


-C


6


alkoxy group, C


1


-C


6


alkylthio group, halo C


1


-C


6


alkylthio group, C


1


-C


6


alkylsulfinyl group, halo C


1


-C


6


alkylsulfinyl group, C


1


-C


6


alkylsulfonyl group, halo C


1


-C


6


alkylsulfonyl group, mono C


1


-C


6


alkylamino group, di C


1


-C


6


alkylamino group in which C


1


-C


6


alkyl groups may be same or different, and C


1


-C


6


alkoxycarbonyl group,




further, an arbitrary saturated carbon atom in said C


1


-C


8


alkylene group, substituted C


1


-C


8


alkylene group, C


3


-C


8


alkenylene group, substituted C


3


-C


8


alkenylene group, C


3


-C


8


alkynylene group and substituted C


3


-C


8


alkynylene group may be substituted with a C


2


-C


5


alkylene group to form a C


3


-C


6


cycloalkane ring, and arbitrary two carbon atoms in said C


1


-C


8


alkylene group, substituted C


1


-C


8


alkylene group, C


3


-C


8


alkenylene group and substituted C


3


-C


8


alkenylene group may be taken conjointly with an alkylene group or an alkenylene group to form a C


3


-C


6


cycloalkane ring or C


3


-C


6


cycloalkene ring;




R


1


represents hydrogen atom, mercapto group, C


1


-C


6


alkylthio group, halo C


1


-C


6


alkylthio group, C


3


-C


6


cycloalkyl group, halo C


3


-C


6


cycloalkyl group, phenyl group, substituted phenyl group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C


1


-C


6


alkyl group, halo C


1


-C


6


alkyl group, C


1


-C


6


alkoxy group, halo C


1


-C


6


alkoxy group, C


1


-C


6


alkylthio group, halo C


1


-C


6


alkylthio group, C


1


-C


6


alkylsulfinyl group, halo C


1


-C


6


alkylsulfinyl group, C


1


-C


6


alkylsulfonyl group, halo C


1


-C


6


alkylsulfonyl group, mono C


1


-C


6


alkylamino group, di C


1


-C


6


alkylamino group in which C


1


-C


6


alkyl groups may be same or different, and C


1


-C


6


alkoxycarbonyl group, phenylthio group, substituted phenylthio group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C


1


-C


6


alkyl group, halo C


1


-C


6


alkyl group, C


1


-C


6


alkoxy group, halo C


1


-C


6


alkoxy group, C


1


-C


6


alkylthio group, halo C


1


-C


6


alkylthio group, C


1


-C


6


alkylsulfinyl group, halo C


1


-C


6


alkylsulfinyl group, C


1


-C


6


alkylsulfonyl group, halo C


1


-C


6


alkylsulfonyl group, mono C


1


-C


6


alkylamino group, di C


1


-C


6


alkylamino group in which C


1


-C


6


alkyl groups may be same or different, and C


1


-C


6


alkoxycarbonyl group, heterocyclic group, substituted heterocyclic group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C


1


-C


6


alkyl group, halo C


1


-C


6


alkyl group, C


1


-C


6


alkoxy group, halo C


1


-C


6


alkoxy group, C


1


-C


6


alkylthio group, halo C


1


-C


6


alkylthio group, C


1


-C


6


alkylsulfinyl group, halo C


1


-C


6


alkylsulfinyl group, C


1


-C


6


alkylsulfonyl group, halo C


1


-C


6


alkylsulfonyl group, mono C


1


-C


6


alkylamino group, di C


1


-C


6


alkylamino group in which C


1


-C


6


alkyl groups may be same or different, and C


1


-C


6


alkoxycarbonyl group, or —A


2


—R


4


[wherein A


2


represents —C(═O)—, —C(═S)—, or —C(═NR


5


)— (in which R


5


represents hydrogen atom, C


1


-C


6


alkyl group, C


1


-C


6


alkoxy group, mono C


1


-C


6


alkylamino group, di C


1


-C


6


alkylamino group in which C


1


-C


6


alkyl groups may be same or different, C


1


-C


6


alkoxycarbonyl group, phenyl group or substituted phenyl group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C


1


-C


6


alkyl group, halo C


1


-C


6


alkyl group, C


1


-C


6


alkoxy group, halo C


1


-C


6


alkoxy group, C


1


-C


6


alkylthio group, halo C


1


-C


6


alkylthio group, C


1


-C


6


alkylsulfinyl group, halo C


1


-C


6


alkylsulfinyl group, C


1


-C


6


alkylsulfonyl group, halo C


1


-C


6


alkylsulfonyl group, mono C


1


-C


6


alkylamino group, di C


1


-C


6


alkylamino group in which C


1


-C


6


alkyl groups may be same or different, and C


1


-C


6


alkoxycarbonyl group),




C


1


-C


8


alkylene group, halo C


1


-C


8


alkylene group, C


3


-C


6


alkenylene group, halo C


3


-C


6


alkenylene group, C


3


-C


6


alkynylene group or halo C


3


-C


6


alkynylene group; and




(1) in cases where A


2


represents —C(═O)—, —C(═S)— or —C(═NR


5


)— wherein R


5


is as defined above, R


4


represents hydrogen atom, C


1


-C


6


alkyl group, halo C


1


-C


6


alkyl group, C


3


-C


6


cycloalkyl group, halo C


3


-C


6


cycloalkyl group, phenyl group, substituted phenyl group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C


1


-C


6


alkyl group, halo C


1


-C


6


alkyl group, C


1


-C


6


alkoxy group, halo C


1


-C


6


alkoxy group, C


1


-C


6


alkylthio group, halo C


1


-C


6


alkylthio group, C


1


-C


6


alkylsulfinyl group, halo C


1


-C


6


alkylsulfinyl group, C


1


-C


6


alkylsulfonyl group, halo C


1


-C


6


alkylsulfonyl group, mono C


1


-C


6


alkylamino group, di C


1


-C


6


alkylamino group in which C


1


-C


6


alkyl groups may be same or different, and C


1


-C


6


alkoxycarbonyl group, heterocyclic group, substituted heterocyclic group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C


1


-C


6


alkyl group, halo C


1


-C


6


alkyl group, C


1


-C


6


alkoxy group, halo C


1


-C


6


alkoxy group, C


1


-C


6


alkylthio group, halo C


1


-C


6


alkylthio group, C


1


-C


6


alkylsulfinyl group, halo C


1


-C


6


alkylsulfinyl group, C


1


-C


6


alkylsulfonyl group, halo C


1


-C


6


alkylsulfonyl group, mono C


1


-C


6


alkylamino group, di C


1


-C


6


alkylamino group in which C


1


-C


6


alkyl groups may be same or different, and C


1


-C


6


alkoxycarbonyl group, or —Z


1


—R


6


wherein Z


1


represents —O—, —S— or —N(R


7


)— (wherein R


7


represents hydrogen atom, C


1


-C


6


alkyl group, C


1


-C


6


alkylcarbonyl group, halo C


1


-C


6


alkylcarbonyl group or C


1


-C


6


alkoxycarbonyl group), and R


6


represents hydrogen atom, C


1


-C


6


alkyl group, halo C


1


-C


6


alkyl group, C


3


-C


6


alkenyl group, halo C


3


-C


6


alkenyl group, C


3


-C


6


alkynyl group, halo C


3


-C


6


alkynyl group, C


3


-C


6


cycloalkyl group, phenyl group, substituted phenyl group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C


1


-C


6


alkyl group, halo C


1


-C


6


alkyl group, C


1


-C


6


alkoxy group, halo C


1


-C


6


alkoxy group, C


1


-C


6


alkylthio group, halo C


1


-C


6


alkylthio group, C


1


-C


6


alkylsulfinyl group, halo C


1


-C


6


alkylsulfinyl group, C


1


-C


6


alkylsulfonyl group, halo C


1


-C


6


alkylsulfonyl group, mono C


1


-C


6


alkylamino group, di C


1


-C


6


alkylamino group in which C


1


-C


6


alkyl groups may be same or different, and C


1


-C


6


alkoxycarbonyl group, phenyl C


1


-C


4


alkyl group, substituted phenyl C


1


-C


4


alkyl group having, on the ring thereof, at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C


1


-C


6


alkyl group, halo C


1


-C


6


alkyl group, C


1


-C


6


alkoxy group, halo C


1


-C


6


alkoxy group, C


1


-C


6


alkylthio group, halo C


1


-C


6


alkylthio group, C


1


-C


6


alkylsulfinyl group, halo C


1


-C


6


alkylsulfinyl group, C


1


-C


6


alkylsulfonyl group, halo C


1


-C


6


alkylsulfonyl group, mono C


1


-C


6


alkylamino group, di C


1


-C


6


alkylamino group in which C


1


-C


6


alkyl groups may be same or different, and C


1


-C


6


alkoxycarbonyl group, heterocyclic group, or substituted heterocyclic group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C


1


-C


6


alkyl group, halo C


1


-C


6


alkyl group, C


1


-C


6


alkoxy group, halo C


1


-C


6


alkoxy group, C


1


-C


6


alkylthio group, halo C


1


-C


6


alkylthio group, C


1


-C


6


alkylsulfinyl group, halo C


1


-C


6


alkylsulfinyl group, C


1


-C


6


alkylsulfonyl group, halo C


1


-C


6


alkylsulfonyl group, mono C


1


-C


6


alkylamino group, di C


1


-C


6


alkylamino group in which C


1


-C


6


alkyl groups may be same or different, and C


1


-C


6


alkoxycarbonyl group, and




(2) in cases where A


2


represents C


1


-C


8


alkylene group, halo C


1


-C


8


alkylene group, C


3


-C


6


alkenylene group, halo C


3


-C


6


alkenylene group, C


3


-C


6


alkynylene group or halo C


3


-C


6


alkynylene group, R


4


represents hydrogen atom, halogen atom, cyano group, nitro group, C


3


-C


6


cycloalkyl group, halo C


3


-C


6


cycloalkyl group, C


1


-C


6


alkoxycarbonyl group, mono C


1


-C


6


alkylaminocarbonyl group, di C


1


-C


6


alkylaminocarbonyl group in which C


1


-C


6


alkyl groups may be same or different, phenyl group, substituted phenyl group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C


1


-C


6


alkyl group, halo C


1


-C


6


alkyl group, C


1


-C


6


alkoxy group, halo C


1


-C


6


alkoxy group, C


1


-C


6


alkylthio group, halo C


1


-C


6


alkylthio group, C


1


-C


6


alkylsulfinyl group, halo C


1


-C


6


alkylsulfinyl group, C


1


-C


6


alkylsulfonyl group, halo C


1


-C


6


alkylsulfonyl group, mono C


1


-C


6


alkylamino group, di C


1


-C


6


alkylamino group in which C


1


-C


6


alkyl groups may be same or different, and C


1


-C


6


alkoxycarbonyl group, heterocyclic group, substituted heterocyclic group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C


1


-C


6


alkyl group, halo C


1


-C


6


alkyl group, C


1


-C


6


alkoxy group, halo C


1


-C


6


alkoxy group, C


1


-C


6


alkylthio group, halo C


1


-C


6


alkylthio group, C


1


-C


6


alkylsulfinyl group, halo C


1


-C


6


alkylsulfinyl group, C


1


-C


6


alkylsulfonyl group, halo C


1


-C


6


alkylsulfonyl group, mono C


1


-C


6


alkylamino group, di C


1


-C


6


alkylamino group in which C


1


-C


6


alkyl groups may be same or different, and C


1


-C


6


alkoxycarbonyl group, or —Z


2


—R


8


wherein Z


2


represents —O—, —S—, —SO—, —SO


2


—, —N(R


9


)— (wherein R


9


represents hydrogen atom, C


1


-C


6


alkyl group, C


1


-C


6


alkylcarbonyl group, halo C


1


-C


6


alkylcarbonyl group, C


1


-C


6


alkoxycarbonyl group, phenylcarbonyl group, or substituted phenylcarbonyl group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C


1


-C


6


alkyl group, halo C


1


-C


6


alkyl group, C


1


-C


6


alkoxy group, halo C


1


-C


6


alkoxy group, C


1


-C


6


alkylthio group, halo C


1


-C


6


alkylthio group, C


1


-C


6


alkylsulfinyl group, halo C


1


-C


6


alkylsulfinyl group, C


1


-C


6


alkylsulfonyl group and halo C


1


-C


6


alkylsulfonyl group), —C(═O)— or —C(═NOR


10


)— (wherein R


10


represents hydrogen atom, C


1


-C


6


alkyl group, halo C


1


-C


6


alkyl group, C


3


-C


6


alkenyl group, halo C


3


-C


6


alkenyl group, C


3


-C


6


alkynyl group, halo C


1


-C


6


alkynyl group, C


3


-C


6


cycloalkyl group, phenyl C


1


-C


4


alkyl group or substituted phenyl C


1


-C


4


alkyl group having, on the ring thereof, at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C


1


-C


6


alkyl group, halo C


1


-C


6


alkyl group, C


1


-C


6


alkoxy group, halo C


1


-C


6


alkoxy group, C


1


-C


6


alkylthio group, halo C


1


-C


6


alkylthio group, C


1


-C


6


alkylsulfinyl group, halo C


1


-C


6


alkylsulfinyl group, C


1


-C


6


alkylsulfonyl group, halo C


1


-C


6


alkylsulfonyl group, mono C


1


-C


6


alkylamino group, di C


1


-C


6


alkylamino group in which C


1


-C


6


alkyl groups may be same or different, and C


1


-C


6


alkoxycarbonyl group) and R


8


represents hydrogen atom, C


1


-C


6


alkyl group, halo C


1


-C


6


alkyl group, C


3


-C


6


alkenyl group, halo C


3


-C


6


alkenyl group, C


3


-C


6


alkynyl group, halo C


3


-C


6


alkynyl group, C


3


-C


6


cycloalkyl group, C


1


-C


6


alkylcarbonyl group, halo C


1


-C


6


alkylcarbonyl group, C


1


-C


6


alkoxycarbonyl group, mono C


1


-C


6


alkylaminocarbonyl group, di C


1


-C


6


alkylaminocarbonyl group in which C


1


-C


6


alkyl groups may be same or different, phenyl group, substituted phenyl group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C


1


-C


6


alkyl group, halo C


1


-C


6


alkyl group, C


1


-C


6


alkoxy group, halo C


1


-C


6


alkoxy group, C


1


-C


6


alkylthio group, halo C


1


-C


6


alkylthio group, C


1


-C


6


alkylsulfinyl group, halo C


1


-C


6


alkylsulfinyl group, C


1


-C


6


alkylsulfonyl group, halo C


1


-C


6


alkylsulfonyl group, mono C


1


-C


6


alkylamino group, di C


1


-C


6


alkylamino group in which C


1


-C


6


alkyl groups may be same or different, and C


1


-C


6


alkoxycarbonyl group, phenyl C


1


-C


4


alkyl group, substituted phenyl C


1


-C


4


alkyl group having, on the ring thereof, at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C


1


-C


6


alkyl group, halo C


1


-C


6


alkyl group, C


1


-C


6


alkoxy group, halo C


1


-C


6


alkoxy group, C


1


-C


6


alkylthio group, halo C


1


-C


6


alkylthio group, C


1


-C


6


alkylsulfinyl group, halo C


1


-C


6


alkylsulfinyl group, C


1


-C


6


alkylsulfonyl group, halo C


1


-C


6


alkylsulfonyl group, mono C


1


-C


6


alkylamino group, di C


1


-C


6


alkylamino group in which C


1


-C


6


alkyl groups may be same or different, and C


1


-C


6


alkoxycarbonyl group, heterocyclic group, or substituted heterocyclic group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C


1


-C


6


alkyl group, halo C


1


-C


6


alkyl group, C


1


-C


6


alkoxy group, halo C


1


-C


6


alkoxy group, C


1


-C


6


alkylthio group, halo C


1


-C


6


alkylthio group, C


1


-C


6


alkylsulfinyl group, halo C


1


-C


6


alkylsulfinyl group, C


1


-C


6


alkylsulfonyl group, halo C


1


-C


6


alkylsulfonyl group, mono C


1


-C


6


alkylamino group, di C


1


-C


6


alkylamino group in which C


1


-C


6


alkyl groups may be same or different, and C


1


-C


6


alkoxycarbonyl group], or




alternatively, R


1


may be combined with A


1


to form a 5- to 8-membered ring which may be intercepted by 1 or 2, same or different oxygen atoms, sulfur atoms or nitrogen atoms;




R


2


and R


3


which may be same or different, represent hydrogen atom, C


3


-C


6


cycloalkyl group or —A


2


—R


4


wherein A


2


and R


4


are as defined above; or




alternatively, R


2


may be combined with A


1


or R


1


to form a 5- to 7-membered ring which may be intercepted by 1 or 2, same or different oxygen atoms, sulfur atoms or nitrogen atoms;




X which may be same or different, represents halogen atom, cyano group, nitro group, C


3


-C


6


cycloalkyl group, halo C


3


-C


6


cycloalkyl group, C


1


-C


6


alkoxycarbonyl group, phenyl group, substituted phenyl group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C


1


-C


6


alkyl group, halo C


1


-C


6


alkyl group, C


1


-C


6


alkoxy group, halo C


1


-C


6


alkoxy group, C


1


-C


6


alkylthio group, halo C


1


-C


6


alkylthio group, C


1


-C


6


alkylsulfinyl group, halo C


1


-C


6


alkylsulfinyl group, C


1


-C


6


alkylsulfonyl group, halo C


1


-C


6


alkylsulfonyl group, mono C


1


-C


6


alkylamino group, di C


1


-C


6


alkylamino group in which C


1


-C


6


alkyl groups may be same or different, and C


1


-C


6


alkoxycarbonyl group, heterocyclic group, substituted heterocyclic group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C


1


-C


6


alkyl group, halo C


1


-C


6


alkyl group, C


1


-C


6


alkoxy group, halo C


1


-C


6


alkoxy group, C


1


-C


6


alkylthio group, halo C


1


-C


6


alkylthio group, C


1


-C


6


alkylsulfinyl group, halo C


1


-C


6


alkylsulfinyl group, C


1


-C


6


alkylsulfonyl group, halo C


1


-C


6


alkylsulfonyl group, mono C


1


-C


6


alkylamino group, di C


1


-C


6


alkylamino group in which C


1


-C


6


alkyl groups may be same or different, and C


1


-C


6


alkoxycarbonyl group, or —A


3


—R


11


[wherein A


3


represents —O—, —S—, —SO—, —SO


2


—, —C(═O)—, —C(═NOR


12


)— (in which R


12


represents hydrogen atom, C


1


-C


6


alkyl group, halo C


1


-C


6


alkyl group, C


3


-C


6


alkenyl group, halo C


3


-C


6


alkenyl group, C


3


-C


6


alkynyl group, C


3


-C


6


cycloalkyl group, phenyl C


1


-C


4


alkyl group or substituted phenyl C


1


-C


4


alkyl group having, on the ring thereof, at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C


1


-C


6


alkyl group, halo C


1


-C


6


alkyl group, C


1


-C


6


alkoxy group, halo C


1


-C


6


alkoxy group, C


1


-C


6


alkylthio group, halo C


1


-C


6


alkylthio group, C


1


-C


6


alkylsulfinyl group, halo C


1


-C


6


alkylsulfinyl group, C


1


-C


6


alkylsulfonyl group, halo C


1


-C


6


alkylsulfonyl group, mono C


1


-C


6


alkylamino group, di C


1


-C


6


alkylamino group in which C


1


-C


6


alkyl groups may be same or different, and C


1


-C


6


alkoxycarbonyl group), C


1


-C


6


alkylene group, halo C


1


-C


6


alkylene group, C


2


-C


6


alkenylene group, halo C


2


-C


6


alkenylene group, C


2


-C


6


alkynylene group or halo C


3


-C


6


alkynylene group; and




(1) in cases where A


3


represents —O—, —S—, —SO— or —SO


2


—, R


11


represents halo C


3


-C


6


cycloalkyl group, halo C


3


-C


6


cycloalkenyl group, phenyl group, substituted phenyl group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C


1


-C


6


alkyl group, halo C


1


-C


6


alkyl group, C


1


-C


6


alkoxy group, halo C


1


-C


6


alkoxy group, C


1


-C


6


alkylthio group, halo C


1


-C


6


alkylthio group, C


1


-C


6


alkylsulfinyl group, halo C


1


-C


6


alkylsulfinyl group, C


1


-C


6


alkylsulfonyl group, halo C


1


-C


6


alkylsulfonyl group, mono C


1


-C


6


alkylamino group, di C


1


-C


6


alkylamino group in which C


1


-C


6


alkyl groups may be same or different, and C


1


-C


6


alkoxycarbonyl group, heterocyclic group, substituted heterocyclic group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C


1


-C


6


alkyl group, halo C


1


-C


6


alkyl group, C


1


-C


6


alkoxy group, halo C


1


-C


6


alkoxy group, C


1


-C


6


alkylthio group, halo C


1


-C


6


alkylthio group, C


1


-C


6


alkylsulfinyl group, halo C


1


-C


6


alkylsulfinyl group, C


1


-C


6


alkylsulfonyl group, halo C


1


-C


6


alkylsulfonyl group, mono C


1


-C


6


alkylamino group, di C


1


-C


6


alkylamino group in which C


1


-C


6


alkyl groups may be same or different, and C


1


-C


6


alkoxycarbonyl group, or —A


4


—R


13


(wherein A


4


represents C


1


-C


6


alkylene group, halo C


1


-C


6


alkylene group, C


3


-C


6


alkenylene group, halo C


3


-C


6


alkenylene group, C


3


-C


6


alkynylene group or halo C


3


-C


6


alkynylene group, and R


13


represents hydrogen atom, halogen atom, C


3


-C


6


cycloalkyl group, halo C


3


-C


6


cycloalkyl group, C


1


-C


6


alkoxycarbonyl group, phenyl group, substituted phenyl group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C


1


-C


6


alkyl group, halo C


1


-C


6


alkyl group, C


1


-C


6


alkoxy group, halo C


1


-C


6


alkoxy group, C


1


-C


6


alkylthio group, halo C


1


-C


6


alkylthio group, C


1


-C


6


alkylsulfinyl group, halo C


1


-C


6


alkylsulfinyl group, C


1


-C


6


alkylsulfonyl group, halo C


1


-C


6


alkylsulfonyl group, mono C


1


-C


6


alkylamino group, di C


1


-C


6


alkylamino group in which C


1


-C


6


alkyl groups may be same or different, and C


1


-C


6


alkoxycarbonyl group, or —A


5


—R


14


(wherein A


5


represents —O—, —S—, —SO—, —SO


2


or —C(═O)—, and R


14


represents C


1


-C


6


alkyl group, halo C


1


-C


6


alkyl group, C


3


-C


6


alkenyl group, halo C


3


-C


6


alkenyl group, C


3


-C


6


alkynyl group, halo C


3


-C


6


alkynyl group, C


3


-C


6


cycloalkyl group, halo C


3


-C


6


cycloalkyl group, phenyl group, substituted phenyl group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C


1


-C


6


alkyl group, halo C


1


-C


6


alkyl group, C


1


-C


6


alkoxy group, halo C


1


-C


6


alkoxy group, C


1


-C


6


alkylthio group, halo C


1


-C


6


alkylthio group, C


1


-C


6


alkylsulfinyl group, halo C


1


-C


6


alkylsulfinyl group, C


1


-C


6


alkylsulfonyl group, halo C


1


-C


6


alkylsulfonyl group, mono C


1


-C


6


alkylamino group, di C


1


-C


6


alkylamino group in which C


1


-C


6


alkyl groups may be same or different, and C


1


-C


6


alkoxycarbonyl group, heterocyclic group, or substituted heterocyclic group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C


1


-C


6


alkyl group, halo C


1


-C


6


alkyl group, C


1


-C


6


alkoxy group, halo C


1


-C


6


alkoxy group, C


1


-C


6


alkylthio group, halo C


1


-C


6


alkylthio group, C


1


-C


6


alkylsulfinyl group, halo C


1


-C


6


alkylsulfinyl group, C


1


-C


6


alkylsulfonyl group, halo C


1


-C


6


alkylsulfonyl group, mono C


1


-C


6


alkylamino group, di C


1


-C


6


alkylamino group in which C


1


-C


6


alkyl groups may be same or different, and C


1


-C


6


alkoxycarbonyl group)), and




(2) in cases where A


3


represents —C(═O)— or —C(═NOR


12


)— wherein R


12


is as defined above, R


11


represents hydrogen atom, C


1


-C


6


alkyl group, halo C


1


-C


6


alkyl group, C


2


-C


6


alkenyl group, halo C


2


-C


6


alkenyl group, C


3


-C


6


cycloalkyl group, halo C


3


-C


6


cycloalkyl group, C


1


-C


6


alkoxy group, C


1


-C


6


alkylthio group, mono C


1


-C


6


alkylamino group, di C


1


-C


6


alkylamino group in which C


1


-C


6


alkyl groups may be same or different, phenyl group, substituted phenyl group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C


1


-C


6


alkyl group, halo C


1


-C


6


alkyl group, C


1


-C


6


alkoxy group, halo C


1


-C


6


alkoxy group, C


1


-C


6


alkylthio group, halo C


1


-C


6


alkylthio group, C


1


-C


6


alkylsulfinyl group, halo C


1


-C


6


alkylsulfinyl group, C


1


-C


6


alkylsulfonyl group, halo C


1


-C


6


alkylsulfonyl group, mono C


1


-C


6


alkylamino group, di C


1


-C


6


alkylamino group in which C


1


-C


6


alkyl groups may be same or different, and C


1


-C


6


alkoxycarbonyl group, phenylamino group, substituted phenylamino group having on the ring thereof, at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C


1


-C


6


alkyl group, halo C


1


-C


6


alkyl group, C


1


-C


6


alkoxy group, halo C


1


-C


6


alkoxy group, C


1


-C


6


alkylthio group, halo C


1


-C


6


alkylthio group, C


1


-C


6


alkylsulfinyl group, halo C


1


-C


6


alkylsulfinyl group, C


1


-C


6


alkylsulfonyl group, halo C


1


-C


6


alkylsulfonyl group, mono C


1


-C


6


alkylamino group, di C


1


-C


6


alkylamino group in which C


1


-C


6


alkyl groups may be same or different, and C


1


-C


6


alkoxycarbonyl group, heterocyclic group, or substituted heterocyclic group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C


1


-C


6


alkyl group, halo C


1


-C


6


alkyl group, C


1


-C


6


alkoxy group, halo C


1


-C


6


alkoxy group, C


1


-C


6


alkylthio group, halo C


1


-C


6


alkylthio group, C


1


-C


6


alkylsulfinyl group, halo C


1


-C


6


alkylsulfinyl group, C


1


-C


6


alkylsulfonyl group, halo C


1


-C


6


alkylsulfonyl group, mono C


1


-C


6


alkylamino group, di C


1


-C


6


alkylamino group in which C


1


-C


6


alkyl groups may be same or different, and C


1


-C


6


alkoxycarbonyl group, and




(3) in cases where A


3


represents C


1


-C


6


alkylene group, halo C


1


-C


6


alkylene group, C


2


-C


6


alkenylene group, halo C


2


-C


6


alkenylene group, C


2


-C


6


alkynylene group or halo C


3


-C


6


alkynylene group, R


11


represents hydrogen atom, hydroxy group, halogen atom, C


3


-C


6


cycloalkyl group, halo C


3


-C


6


cycloalkyl group, C


1


-C


6


alkoxycarbonyl group, phenyl group, substituted phenyl group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C


1


-C


6


alkyl group, halo C


1


-C


6


alkyl group, C


1


-C


6


alkoxy group, halo C


1


-C


6


alkoxy group, C


1


-C


6


alkylthio group, halo C


1


-C


6


alkylthio group, C


1


-C


6


alkylsulfinyl group, halo C


1


-C


6


alkylsulfinyl group, C


1


-C


6


alkylsulfonyl group, halo C


1


-C


6


alkylsulfonyl group, mono C


1


-C


6


alkylamino group, di C


1


-C


6


alkylamino group in which C


1


-C


6


alkyl groups may be same or different, and C


1


-C


6


alkoxycarbonyl group, heterocyclic group, substituted heterocyclic group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C


1


-C


6


alkyl group, halo C


1


-C


6


alkyl group, C


1


-C


6


alkoxy group, halo C


1


-C


6


alkoxy group, C


1


-C


6


alkylthio group, halo C


1


-C


6


alkylthio group, C


1


-C


6


alkylsulfinyl group, halo C


1


-C


6


alkylsulfinyl group, C


1


-C


6


alkylsulfonyl group, halo C


1


-C


6


alkylsulfonyl group, mono C


1


-C


6


alkylamino group, di C


1


-C


6


alkylamino group in which C


1


-C


6


alkyl groups may be same or different, and C


1


-C


6


alkoxycarbonyl group, or —A


6


—R


15


(wherein A


6


represents —O—, —S—, —SO— or —SO


2


—, and R


15


represents C


3


-C


6


cycloalkyl group, halo C


3


-C


6


cycloalkyl group, phenyl group, substituted phenyl group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C


1


-C


6


alkyl group, halo C


1


-C


6


alkyl group, C


1


-C


6


alkoxy group, halo C


1


-C


6


alkoxy group, C


1


-C


6


alkylthio group, halo C


1


-C


6


alkylthio group, C


1


-C


6


alkylsulfinyl group, halo C


1


-C


6


alkylsulfinyl group, C


1


-C


6


alkylsulfonyl group, halo C


1


-C


6


alkylsulfonyl group, mono C


1


-C


6


alkylamino group, di C


1


-C


6


alkylamino group in which C


1


-C


6


alkyl groups may be same or different, and C


1


-C


6


alkoxycarbonyl group, heterocyclic group, substituted heterocyclic group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C


1


-C


6


alkyl group, halo C


1


-C


6


alkyl group, C


1


-C


6


alkoxy group, halo C


1


-C


6


alkoxy group, C


1


-C


6


alkylthio group, halo C


1


-C


6


alkylthio group, C


1


-C


6


alkylsulfinyl group, halo C


1


-C


6


alkylsulfinyl group, C


1


-C


6


alkylsulfonyl group, halo C


1


-C


6


alkylsulfonyl group, mono C


1


-C


6


alkylamino group, di C


1


-C


6


alkylamino group in which C


1


-C


6


alkyl groups may be same or different, and C


1


-C


6


alkoxycarbonyl group, or —A


7


—R


16


(wherein A


7


represents C


1


-C


6


alkylene group, halo C


1


-C


6


alkylene group, C


2


-C


6


alkenylene group, halo C


2


-C


6


alkenylene group, C


2


-C


6


alkynylene group or halo C


3


-C


6


alkynylene group, and R


16


represents hydrogen atom, halogen atom, C


3


-C


6


cycloalkyl group, halo C


3


-C


6


cycloalkyl group, C


1


-C


6


alkoxy group, halo C


1


-C


6


alkoxy group, C


1


-C


6


alkylthio group, halo C


1


-C


6


alkylthio group, C


1


-C


6


alkylsulfinyl group, halo C


1


-C


6


alkylsulfinyl group, cl-C


6


alkylsulfonyl group, halo C


1


-C


6


alkylsulfonyl group, phenyl group, substituted phenyl group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C


1


-C


6


alkyl group, halo C


1


-C


6


alkyl group, C


1


-C


6


alkoxy group, halo C


1


-C


6


alkoxy group, C


1


-C


6


alkylthio group, halo C


1


-C


6


alkylthio group, C


1


-C


6


alkylsulfinyl group, halo C


1


-C


6


alkylsulfinyl group, C


1


-C


6


alkylsulfonyl group, halo C


1


-C


6


alkylsulfonyl group, mono C


1


-C


6


alkylamino group, di C


1


-C


6


alkylamino group in which C


1


-C


6


alkyl groups may be same or different, and C


1


-C


6


alkoxycarbonyl group, phenoxy group, substituted phenoxy group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C


1


-C


6


alkyl group, halo C


1


-C


6


alkyl group, C


1


-C


6


alkoxy group, halo C


1


-C


6


alkoxy group, C


1


-C


6


alkylthio group, halo C


1


-C


6


alkylthio group, C


1


-C


6


alkylsulfinyl group, halo C


1


-C


6


alkylsulfinyl group, C


1


-C


6


alkylsulfonyl group, halo C


1


-C


6


alkylsulfonyl group, mono C


1


-C


6


alkylamino group, di C


1


-C


6


alkylamino group in which C


1


-C


6


alkyl groups may be same or different, and C


1


-C


6


alkoxycarbonyl group, phenylthio group, substituted phenylthio group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C


1


-C


6


alkyl group, halo C


1


-C


6


alkyl group, C


1


-C


6


alkoxy group, halo C


1


-C


6


alkoxy group, C


1


-C


6


alkylthio group, halo C


1


-C


6


alkylthio group, C


1


-C


6


alkylsulfinyl group, halo C


1


-C


6


alkylsulfinyl group, C


1


-C


6


alkylsulfonyl group, halo C


1


-C


6


alkylsulfonyl group, mono C


1


-C


6


alkylamino group, di C


1


-C


6


alkylamino group in which C


1


-C


6


alkyl groups may be same or different, and C


1


-C


6


alkoxycarbonyl group, heterocyclic group, or substituted heterocyclic group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C


1


-C


6


alkyl group, halo C


1


-C


6


alkyl group, C


1


-C


6


alkoxy group, halo C


1


-C


6


alkoxy group, C


1


-C


6


alkylthio group, halo C


1


-C


6


alkylthio group, C


1


-C


6


alkylsulfinyl group, halo C


1


-C


6


alkylsulfinyl group, C


1


-C


6


alkylsulfonyl group, halo C


1


-C


6


alkylsulfonyl group, mono C


1


-C


6


alkylamino group, di C


1


-C


6


alkylamino group in which C


1


-C


6


alkyl groups may be same or different, and C


1


-C


6


alkoxycarbonyl group))]; and l represents an integer of 0 to 4; and




alternatively, X may be taken conjointly with the adjacent carbon atom on the phenyl ring to form a fused ring, and said fused ring may have at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C


1


-C


6


alkyl group, halo C


1


-C


6


alkyl group, C


1


-C


6


alkoxy group, halo C


1


-C


6


alkoxy group, C


1


-C


6


alkylthio group, halo C


1


-C


6


alkylthio group, C


1


-C


6


alkylsulfinyl group, halo C


1


-C


6


alkylsulfinyl group, C


1


-C


6


alkylsulfonyl group, halo C


1


-C


6


alkylsulfonyl group, mono C


1


-C


6


alkylamino group, di C


1


-C


6


alkylamino group in which C


1


-C


6


alkyl groups may be same or different, and C


1


-C


6


alkoxycarbonyl group; and




Y may be same or different and represents halogen atom, cyano group, nitro group, halo C


3


-C


6


cycloalkyl group, tri C


1


-C


6


alkylsilyl group in which C


1


-C


6


alkyl groups may be same or different, phenyl group, substituted phenyl group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C


1


-C


6


alkyl group, halo C


1


-C


6


alkyl group, C


1


-C


6


alkoxy group, halo C


1


-C


6


alkoxy group, C


1


-C


6


alkylthio group, halo C


1


-C


6


alkylthio group, C


1


-C


6


alkylsulfinyl group, halo C


1


-C


6


alkylsulfinyl group, C


1


-C


6


alkylsulfonyl group, halo C


1


-C


6


alkylsulfonyl group, mono C


1


-C


6


alkylamino group, di C


1


-C


6


alkylamino group in which C


1


-C


6


alkyl groups may be same or different, and C


1


-C


6


alkoxycarbonyl group, heterocyclic group, substituted heterocyclic group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C


1


-C


6


alkyl group, halo C


1


-C


6


alkyl group, C


1


-C


6


alkoxy group, halo C


1


-C


6


alkoxy group, C


1


-C


6


alkylthio group, halo C


1


-C


6


alkylthio group, C


1


-C


6


alkylsulfinyl group, halo C


1


-C


6


alkylsulfinyl group, C


1


-C


6


alkylsulfonyl group, halo C


1


-C


6


alkylsulfonyl group, mono C


1


-C


6


alkylamino group, di C


1


-C


6


alkylamino group in which C


1


-C


6


alkyl groups may be same or different, and C


1


-C


6


alkoxycarbonyl group, or —A


3


—R


11


wherein A


3


and R


11


are as defined above; and m represents an integer of 0 to 5; and




Y may be taken conjointly with an adjacent carbon atom on the phenyl ring to form a fused ring, and said fused ring may have at least one, same or different substituents selected from the group consisting of halogen atom, C


1


-C


6


alkyl group, halo C


1


-C


6


alkyl group, C


1


-C


6


alkoxy group, halo C


1


-C


6


alkoxy group, C


1


-C


6


alkylthio group, halo C


1


-C


6


alkylthio group, C


1


-C


6


alkylsulfinyl group, halo C


1


-C


6


alkylsulfinyl group, C


1


-C


6


alkylsulfonyl group, halo C


1


-C


6


alkylsulfonyl group, phenyl group, substituted phenyl group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C


1


-C


6


alkyl group, halo C


1


-C


6


alkyl group, C


1


-C


6


alkoxy group, halo C


1


-C


6


alkoxy group, C


1


-C


6


alkylthio group, halo C


1


-C


6


alkylthio group, C


1


-C


6


alkylsulfinyl group, halo C


1


-C


6


alkylsulfinyl group, C


1


-C


6


alkylsulfonyl group, halo C


1


-C


6


alkylsulfonyl group, mono C


1


-C


6


alkylamino group, di C


1


-C


6


alkylamino group in which C


1


-C


6


alkyl groups may be same or different, and C


1


-C


6


alkoxycarbonyl group, heterocyclic group, and substituted heterocyclic group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C


1


-C


6


alkyl group, halo C


1


-C


6


alkyl group, C


1


-C


6


alkoxy group, halo C


1


-C


6


alkoxy group, C


1


-C


6


alkylthio group, halo C


1


-C


6


alkylthio group, C


1


-C


6


alkylsulfinyl group, halo C


1


-C


6


alkylsulfinyl group, C


1


-C


6


alkylsulfonyl group, halo C


1


-C


6


alkylsulfonyl group, mono C


1


-C


6


alkylamino group, di C


1


-C


6


alkylamino group in which C


1


-C


6


alkyl groups may be same or different, and C


1


-C


6


alkoxycarbonyl group; and




n represents an integer of 0 to 2;




provided that when X, R


2


and R


3


simultaneously represent hydrogen atom, m represents an integer of 2, Y of the 2-position represents fluorine atom and Y of the 3-position represents chlorine atom, then A


1


is not propylene group, R


1


is not methyl group and n is not an integer of 0.




In the definition of the general formula (I) representing the phthalamide derivative of the present invention, the term “halogen atom” means chlorine atom, bromine atom, iodine atom or fluorine atom; the term “C


1


-C


6


alkyl”, means a straight or branched chain alkyl group having 1 to 6 carbon atoms such as methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, s-butyl, t-butyl, n-pentyl, n-hexyl and the like; the term “halo C


1


-C


6


alkyl” means a straight or branched chain alkyl group having 1 to 6 carbon atoms which may be substituted with at least one, same or different halogen atoms; the term “C


1


-C8 alkylene” means a straight or branched chain alkylene group having 1 to 8 carbon atoms such as methylene, ethylene, propylene, trimethylene, dimethylmethylene, tetramethylene, isobutylene, dimethylethylene, octamethylene and the like; the term “a 5- to 8- or 5- to 7-membered ring which may be intercepted by 1 to 2, same or different oxygen atoms, sulfur atoms or nitrogen atoms formed by R


1


with A


1


, or R


2


with A


1


or R


1


” means, for example, perhydrothiazine ring, thiazolidine ring, thiazetidine ring, dihydrothiazine ring, thiazoline ring, perhydroxathiazine ring, dihydroxathiazine ring, dithiazine ring, perhydrodithiazine ring, and the like.




The term “heterocyclic group” means 5- to 6-membered heterocyclic group having one or more same or different hetero atoms selected from oxygen atoms, sulfur atoms or nitrogen atoms such as pyridyl group, pyridine-N-oxide group, pyrimidinyl group, furyl group, tetrahydrofuryl group, thienyl group, tetrahydrothienyl group, tetrahydropyranyl group, tetrahydrothiopyranyl group, oxazolyl group, isoxazolyl group, oxadiazolyl group, thiazolyl group, isothiazolyl group, thiadiazolyl group, imidazolyl group, trithiazolyl group, pyrazolyl group, and the like. As the “fused ring”, there can be exemplified naphthalene, tetrahydronaphthalene, indene, indane, quinoline, quinazoline, indole, indoline, coumarone, isocoumarone, benzodioxane, benzodioxole, benzofuran, dihydrobenzofuran, benzothiophene, dihydrobenzothiophene, benzoxazole, benzothiazole, benzimidazole, indazole, and the like.




As a salt of a phthalamide derivative represented by the general formula (I) of the present invention, there can be exemplified inorganic acid salt such as hydrochlorate, sulfate, nitrate, phosphate and the like; organic acid salt such as acetate, fumarate, maleate, oxalate, methanesulfonate, benzenesulfonate, p-toluenesulfonate and the like; and salt of metallic ion such as sodium ion, potassium ion, calcium ion and the like.




Some of the phthalamide derivatives represented by the general formula (I) of the present invention contain an asymmetric carbon atom or an asymmetric center in the structural formula thereof, and in some cases there can exist two optical isomers. The present invention includes all these optical isomers and all the mixtures consisting of arbitrary proportions of these optical isomers.




Preferable examples of each substituent of the phthalamide derivative of general formula (I) or salt thereof of the present invention are A


1


is a straight or branched C


1


-C


8


alkylene group; R


1


is C


1


-C


6


alkyl group or halo C


1


-C


6


alkyl group; each of R


2


and R


3


is hydrogen atom or C


1


-C


6


alkyl group; X is halogen atom, nitro group, C


1


-C


6


alkyl group, halo C


1


-C


6


alkyl group or halo C


1


-C


6


alkoxy group; and Y is halogen atom, C


1


-C


6


alkyl group, halo C


1


-C


6


alkyl group or halo C


1


-C


6


alkoxy group.




The phthalamide derivatives of the present invention represented by the general formula (I) can be produced, for example, by the production processes mentioned below.











wherein R


1


, R


2


, A


1


, X, Y, l, m and n are as defined above.




A phthalic anhydride derivative of the general formula (V) is reacted with an aniline of the general formula (IV) in the presence of an inert solvent to obtain a phthalimide derivative of the general formula (III). The phthalimide derivative (III) is reacted with an amine of the general formula (II) after or without being isolated, whereby a phthalamide derivative of the general formula (I-1) can be produced.




(1) General Formula (V)→General Formula (III)




As the inert solvent used in this reaction, any solvent may be used so long as it does not markedly inhibit the progress of the reaction. There can be exemplified aromatic hydrocarbons such as benzene, toluene, xylene, etc.; halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride, etc., chlorinated aromatic hydrocarbons such as chlorobenzene, dichlorobenzene, etc.; acyclic or cyclic ethers such as diethyl ether, dioxane, tetrahydrofuran, etc., esters such as ethyl acetate, etc.; amides such as dimethylformamide, dimethylacetamide, etc.; acids such as acetic acid, etc.; dimethyl sulfoxide; and 1,3-dimethyl-2-imidazolidinone. These inert solvents may be used alone or as a mixture thereof.




Since the reaction is an equimolar reaction, it is sufficient that the reactants are used in equimolar amounts, though either of them may be used in excess. If necessary, the reaction may be carried out under dehydrating conditions.




As to the reaction temperature, the reaction can be carried out in a temperature range of room temperature to the reflux temperature of the inert solvent used. Although the reaction time is varied depending on the scale of reaction, the reaction temperature, etc., it may be properly chosen in a range of several minutes to 48 hours.




After completion of the reaction, the desired compound is isolated from the reaction solution containing the desired compound by a conventional method, and if necessary, purified by recrystallization, column chromatography, etc., whereby the desired compound can be produced. The desired compound can be subjected to the subsequent reaction without isolation from the reaction solution.




The phthalic anhydride derivative of the general formula (V) can be produced by the process described in J. Org. Chem., 52, 129 (1987), J. Am. Chem. Soc., 51, 1865 (1929), J. Am. Chem. Soc., 63, 1542 (1941), etc. The aniline of the general formula (IV) can be produced by the process described in J. Org. Chem., 29, 1 (1964), Angew. Chem. Int. Ed. Engl., 24, 871 (1985), Synthesis, 1984, 667, Bulletin of the Chemical Society of Japan, 1973, 2351, DE-2606982, JP-A-1-90163, etc.




(2) General Formula (III)→General Formula (I-1)




In this reaction, there can be used the inert solvents exemplified above as the inert solvent used in the reaction (1).




Since the reaction is an equimolar reaction, it is sufficient that the reactants are used in equimolar amounts, though the amine of the general formula (II) may be used in excess.




As to the reaction temperature, the reaction can be carried out in a temperature range of room temperature to the reflux temperature of the inert solvent used. Although the reaction time is varied depending on the scale of reaction, the reaction temperature, etc., it may be properly chosen in a range of several minutes to 48 hours.




After completion of the reaction, the desired compound is isolated from the reaction solution containing the desired compound by a conventional method, and if necessary, purified by recrystallization, column chromatography, etc., whereby the desired compound can be produced.











wherein R


1


, R


2


, A


1


, X, Y, l, m and n are as defined above, X′ is a halogen atom or a nitro group, provided that X is other than a hydrogen atom or a nitro group.




A phthalimide derivative of the general formula (III-1) is reacted with a reactant corresponding to X in the presence of an inert solvent to obtain a phthalimide derivative of the general formula (III). The phthalimide derivative (III) is reacted with an amine of the general formula (II) after or without being isolated, whereby a phthalamide derivative of the general formula (I-1) can be produced.




(1) General Formula (III-1)→General Formula (III)




This reaction can be carried out according to the methods described in J. Org. Chem., 42, 3415 (1977), Tetrahedron, 25, 5921 (1969), Synthesis, 1984, 667, Chem. Lett., 1973, 471, J. Org. Chem., 39, 3318 (1974), J. Org. Chem., 39, 3327 (1974), etc.




(2) General Formula (III)→General Formula (I-1)




This reaction can be carried out according to production process 1-(2).











wherein R


1


, R


2


, R


3


, A


1


, X, Y, l, m and n are as defined above.




A phthalic anhydride derivative of the general formula (V) is reacted with an amine of the general formula (II) in the presence of an inert solvent to obtain a phthalamic acid of the general formula (III-4). The phthalamic acid (III-4) is treated as follows after or without isolation. When R


2


of the phthalamic acid (III-4) is a hydrogen atom, the phthalamic acid (III-4) is condensed into a compound of the general formula (VI) in the presence of a condensing agent, and the compound (VI) is reacted with an aniline of the general formula (IV′) in the presence of an inert solvent after or without being isolated. When R


2


of the phthalamic acid (III-4) is other than a hydrogen atom, the phthalamic acid (III-4) is condensed with an aniline of the general formula (IV) in the presence of a condensing agent. Thus, a phthalamide derivative of the general formula (I) can be produced.




Alternatively, a phthalic anhydride derivative of the general formula (V) is reacted with an aniline of the general formula (IV′) in the presence of an inert solvent to obtain a phthalamic acid of the general formula (III-5). The phthalamic acid (III-5) is treated as follows after or without isolation. When R


3


of the phthalamic acid (III-5) is a hydrogen atom, the phthalamic acid (III-5) is condensed into a compound of the general formula (VI-1) in the presence of a condensing agent, and the compound (VI-1) is reacted with an amine of the general formula (II) in the presence of an inert solvent after or without being isolated. When R


3


of the phthalamic acid (III-5) is other than a hydrogen atom, the phthalamic acid (III-5) is condensed with an amine of the general formula (II) in the presence of a condensing agent. Thus, a phthalamide derivative of the general formula (I) can be produced.




(1) General formula (V) or general formula (VI-1)→General Formula (III-4) or General Formula (I), respectively




The desired compound can be produced by this reaction in the same manner as in production process 1-(2).




(2) General Formula (III-4) or General Formula (III-5)→General Formula (VI) or General Formula (VI-1), respectively




The desired compound can be produced by this reaction according to the method described in J. Med. Chem., 10, 982 (1967).




(3) General Formula (VI) or General Formula (V)→General Formula (I) or General Formula (VII-5), respectively




The desired compound can be produced by this reaction in the same manner as in production process 1-(2).




(4) General Formula (III-4) or General Formula (III-5)→General Formula (I)




The desired compound can be produced by reacting the phthalamic acid derivative of the general formula (III-4) or the general formula (III-5) with the aniline of the general formula (IV′) or the amine of the general formula (II), respectively, in the presence of a condensing agent and an inert solvent. If necessary, the reaction can be carried out in the presence of a base.




The inert solvent used in the reaction includes, for example, tetrahydrofuran, diethyl ether, dioxane, chloroform and dichloromethane. As the condensing agent used in the reaction, any condensing agent may be used so long as it is used in usual amide synthesis. The condensing agent includes, for example, Mukaiyama reagent (e.g. 2-chloro-N-methylpyridinium iodide), 1,3-dicyclohexylcarbodiimide (DCC), carbonyldiimidazole (CDI) and diethyl phosphorocyanidate (DEPC). The amount of the condensing agent used may be properly chosen in a range of 1 mole to excess moles per mole of the phthalamic acid derivative of the general formula (III-4) or the general formula (III-5).




As the base usable in the reaction, there can be exemplified organic bases such as triethylamine, pyridine, etc. and inorganic bases such as potassium carbonate, etc. The amount of the base used may be properly chosen in a range of 1 mole to excess moles per mole of the phthalamic acid derivative of the general formula (III-4) or the general formula (III-5).




As to the reaction temperature, the reaction can be carried out in a temperature range of 0° C. to the boiling point of the inert solvent used. Although the reaction time is varied depending on the scale of reaction, the reaction temperature, etc., it ranges from several minutes to 48 hours.




After completion of the reaction, the desired compound is isolated from the reaction solution containing the desired compound by a conventional method, and if necessary, purified by recrystallization, column chromatography, etc., whereby the desired compound can be produced.











wherein R


1


, R


2


, A


1


, X, Y, l, m and n are as defined above, and Hal is halogen atom.











wherein R


1


, Y and m are as defined above.




A benzoyl halide of the general formula (VII) is reacted with an amine derivative of the general formula (II) or (IV′) in the presence of an inert solvent to obtain a benzamide of the general formula (VIII-1) or (VIII-2). The benzamide (VIII-1) or (VIII-2) is ortho-metallized with a metallic reagent such as butyllithium or the like and then directly reacted with an isocyanate of the general formula (IX-1) or (IX-2). Alternatively, the benzamide (VIII-1) or (VIII-2) is reacted with carbon dioxide to obtain a phthalamic acid of the general formula (III-4′) or (III-5′) and then treated in the same manner as in Production process 3-(1) to (4). Thus, a phthalamide derivative of the general formula (I) can be produced.




(1) General Formula (VII)→General Formula (VIII-1) or General Formula (VIII-2)




The desired compound can be produced according to the description of J. Org. Chem. 32, 3069 (1967), etc.




(2) General Formula (VIII-1) or General Formula (VIII-2)→General Formula (I)




The desired compound can be produced by converting a benzamide of the general formula (VIII-1) or (VIII-2) into an ortho-lithio compound according to the description of J. Org. Chem. 29, 853 (1964) and then reacted with an isocyanate of the general formula (IX-1) or (IX-2) at a temperature of −80° C. to room temperature, whereby the desired compound can be produced.




(3) General Formula (VIII-1) or General Formula (VIII-2)→General Formula (III-4′) or General Formula (III-5′), respectively




The desired compound can be produced by the same conversion into an ortho-lithio compound as in (2), followed by introduction of carbon dioxide at a temperature of −80° C. to room temperature.




After completion of the reaction, the desired compound is isolated from the reaction solution by the conventional method and, if necessary, purified by recrystallization, column chromatography, etc., whereby the desired compound can be produced.




(4) General Formula (III-4′) or General Formula (III-5′)→General Formula (I)




The desired compound can be produced by the same procedure as in production process 3-(1) to (4).











wherein R


1


, R


2


, R


3


, A


1


, X, Y, l, m and n are as defined above, provided that n cannot be an integer of 0.




A phthalamide derivative of the general formula (I-2) is reacted with an oxidant in the presence of an inert solvent, whereby a phthalamide derivative of the general formula (I-3) can be produced.




As the inert solvent used in this reaction, there can be exemplified halogenated hydrocarbons such as dichloromethane, chloroform, etc., aromatic hydrocarbon such as toluene, xylene, etc., acids such as acetic acid, etc., and alcohols such as methanol, ethanol, propanol, etc.




As the oxidant, there can be exemplified m-chloroperbenzoic acid, peracetic acid, potassium metaperiodate, potassium hydrogen persulfate (Oxon), hydrogen peroxide, etc. The amount of the oxidant may be properly selected in the range of 0.5 to 3 equivalents per equivalent of the phthalic acid diamide derivative of the general formula (I-2).




As to the reaction temperature, the reaction can be carried out in a temperature range of −50° C. to the boiling temperature zone of the inert solvent used. Though the reaction time is varied depending on the reaction temperature and scale of the reaction, it is in the range of several minutes to 24 hours.




After completion of the reaction, the desired compound is isolated from the reaction solution containing the desired compound by a conventional method and, if necessary, purified by recrystallization, column chromatography, etc., whereby the desired compound can be produced.











Next, typical phthalamide derivatives of the general formula (I) are exemplified in Tables 1, 2 and 3. The present invention is by no means limited by these examples.



















TABLE 1











(R


2


═R


3


═H)



















Property






No




T


1






(X)1




(Y)m




mp (° C.)


















1




CH(CH


3


)CH


2


SCH


3






3-I




2-CH


3


-4-C


2


F


5






179-180






2




CH(CH


3


)CH


2


S-i-C


3


H


7






3-I




2-CH


3


-4-C


2


F


5






Paste






3




CH(CH


3


)CH


2


SCH


3






3-I




2-CH


3


-4-OCF


3






147






4




CH(CH


3


)CH


2


SCH


3






3-I




2-CH


3


-4-OCHF


2






107






5




CH(CH


3


)CH


2


S-i-C


3


H


7






3-I




2-CH


3


-4-OCF


3






126






6




CH(CH


3


)CH


2


SCH


3






3-I




2-CH


3


-4-i-C


3


F


7






197-199






7




CH(CH


3


)CH


2


SCH


3






3-I




2-Cl-4-C


2


F


5






143






8




CH(CH


3


)CH


2


SCH


3






3-I




4-OCF


3






171-178






9




CH(CH


3


)CH


2


SCH


3






3-I




2-CH


3


-4-Cl




179






10




CH(CH


3


)CH


2


SCH


3






3-F




2-CH


3


-4-i-C


3


F


7






146-154






11




CH(CH


3


)CH


2


SCH


3






3-F




2-CH


3


-4-C


2


F


5






140






12




CH(CH


3


)CH


2


SCH


3






3-F




2-CH


3


-4-OCF


3






122-130






13




CH(CH


3


)CH


2


SCH


3






3-F




2-CH


3


-4-OCHF


2






149-154






14




CH(CH


3


)CH


2


SCH


3






H




2-CH


3


-4-C


2


F


5






139-146






15




CH(CH


3


)CH


2


SCH


3






H




2-CH


3


-4-OCF


3






140-144






16




CH(CH


3


)CH


2


SCH


3






H




2-CH


3


-4-i-C


3


F


7






139-145






17




CH(CH


3


)CH


2


SPh




3-I




2-CH


3


-4-C


2


F


5






Paste






18




CH(CH


3


)CH


2


SPh




3-l




2-CH


3


-4-OCF


3






Paste






19




CH(CH


3


)CH


2


SPh




3-I




2-CH


3


-4-i-C


3


F


7






Paste






20




CH(CH


3


)CH


2


SPh




3-I




2-C


2


H


5


-4-C


2


F


5






Paste






21




CH(CH


3


)CH


2


SC


2


H


5






3-I




2-CH


3


-4-C


2


F


5






Paste






22




CH(CH


3


)CH


2


SC


2


H


5






3-I




2-CH


3


-4-i-C


3


F


7






107






23




CH(CH


3


)CH


2


SC


2


H


5






3-I




2-CH


3


-4-OCF


3






143






24




CH(CH


3


)CH


2


SC


2


H


5






3-I




2-CH


3


-4-Cl




161-166






25




CH(CH


3


)CH


2


SC


2


H


5






3-F




2-CH


3


-4-i-C


3


F


7






142






26




CH(CH


3


)CH


2


SC


2


H


5






3-F




2-CH


3


-4-C


2


F


5






Paste






27




CH(CH


3


)CH


2


SC


2


H


5






3-F




2-CH


3


-4-OCF


3






142-147






28




CH(CH


3


)CH


2


SOCH


3






3-I




2-CH


3


-4-C


2


F


5






 94






29




CH(CH


3


)CH


2


SO


2


CH


3






3-I




2-CH


3


-4-C


2


F


5






100






30




CH(CH


3


)CH


2


SOCH


3






3-I




2-CH


3


-4-i-C


3


F


7






 82






31




CH(CH


3


)CH


2


SO


2


CH


3






3-I




2-CH


3


-4-i-C


3


F


7






134






32




CH(CH


3


)CH


2


SCH


3






3-I




2-CH


3


-4-SCF


3






194-195






33




CH(CH


3


)CH


2


S-i-C


4


H


9






3-I




2-CH


3


-4-i-C


3


F


7






164-172






34




CH(CH


3


)CH


2


S-i-C


4


H


9






3-I




2-CH


3


-4-C


2


F


5






159-160






35




CH(CH


3


)CH


2


S-i-C


4


H


9






3-I




2-CH


3


-4-OCF


3






155-159






36




CH(CH


2


SCH


3


)


2






3-I




2-CH


3


-4-C


2


F


5






145






37




CH(CH


3


)CH


2


SCH


3






3,4-Cl


2






2-CH


3


-4-OCF


3






197-199






38




CH(CH


3


)CH


2


SCH


3






5,6-Cl


2






2-CH


3


-4-OCF


3






213-214






39




CH(CH


3


)CH


2


SCH


3






3,4-Cl


2






2-CH


3


-4-C


2


F


5






221-222






40




CH(CH


3


)CH


2


SCH


3






5,6-Cl


2






2-CH


3


-4-C


2


F


5






199-200






41




CH(CH


3


)CH


2


SCH


3






3,4-Cl


2






2-CH


3


-4-i-C


3


F


7






215-216






42




CH(CH


3


)CH


2


SCH


3






5,6-Cl


2






2-CH


3


-4-i-C


3


F


7






220-221






43




CH(CH


3


)CH


2


SCH


3






4-Cl




2-CH


3


-4-C


2


F


5






178-179






44




CH(CH


3


)CH


2


SCH


3






3,4-F


2






2-CH


3


-4-OCF


3






175-176






45




CH(CH


3


)CH


2


SCH


3






4,5-F


2






2-CH


3


-4-OCF


3






118-120






46




CH(CH


3


)CH


2


SCH


3






3-I




2-CH


3


-4-OC—




196-197









(C


2


H


5


)═C(CF


3


)


2








47




CH(CH


3


)CH


2


SCH


3






3-I




2-Cl-4-OCF


2


—CHFO-5




198






48




CH(CH


3


)CH


2


SCH


3






3-I




2-Cl-4-OCHF-CF


2


O-5




192






49




CH(CH


3


)CH


2


SCH


3






3-I




2-OCH


3


-4-C


2


F


5






170






50




CH(CH


3


)CH


2


SCH


3






3-I




2-C


2


H


5


-4-C


2


F


5






125






51




(CH


2


)


2


SCH


3






6-I




2-CH


3


-4-OCF


3






130-133






52




(CH


2


)


2


SCH


3






3-I




2-CH


3


-4-OCF


3






145-150






53




(CH


2


)


2


SCH


3






3-I




2-CH


3


-4-C


2


F


5






Amorphous






54




(CH


2


)


2


SCH


3






3-I




2-CH


3


-4-i-C


3


F


7






Amorphous






55




(CH


2


)


3


SCH


3






3-I




2-CH


3


-4-OCF


3






144-147






56




(CH


2


)


3


SCH


3






3-I




2-CH


3


-4-C


2


F


5






165-168






57




(CH


2


)


3


SCH


3






3-I




2-CH


3


-4-i-C


3


F


7






156-159






58




(CH


2


)


2


S-i-C


3


H


7






3-I




2-CH


3


-4-OCF


3






189-192






59




(CH


2


)


2


S-i-C


3


H


7






3-I




2-CH


3


-4-C


2


F


5






153-155






60




(CH


2


)


2


S-i-C


3


H


7






3-I




2-CH


3


-4-i-C


3


F


7






158-160






61




CH(CH


3


)CH


2


S-2-Pyi




3-I




2-CH


3


-4-C


2


F


5






Amorphous






62




CH(CH


3


)CH


2


S-2-Pyi




3-I




2-CH


3


-4-i-C


3


F


7






140-142






63




CH(CH


3


)CH


2


S-n-C


4


H


9






3-I




2-CH


3


-4-OCF


3






137-139






64




CH(CH


3


)CH


2


S-n-C


4


H


9






3-I




2-CH


3


-4-C


2


F


5






Amorphous






65




CH(CH


3


)CH


2


SCH


3






3-I




2-Cl-4-i-C


3


F


7






190






66




CH(CH


3


)CH


2


SCH


3






3-I




2-C


2


H


5


-4-i-C


3


F


7






205






67




CH(CH


2


SCH


3


)


2






3-I




2-CH


3


-4-i-C


3


F


7






181






68




CH(CH


2


SCH


3


)


2






3-I




2-CH


3


-4-OCF


2


CHF


2






169-176






69




CH(CH


2


SCH


3


)


2






3-I




2-CH


3


-4-OCF


3






131-139






70




CH(CH


2


SCH


3


)


2






3-I




2-CH


3


-4-OCHF


2






142






71




(CH


2


)


2


SC


2


H


5






3-I




2-CH


3


-4-OCF


3






157-161






72




(CH


2


)


2


SC


2


H


5






3-I




2-CH


3


-4-C


2


F


5






152-155






73




(CH


2


)


2


SC


2


H


5






3-I




2-CH


3


-4-i-C


3


F


7






159-162






74




CH(CH


3


)CH


2


S-2-Pyi




3-I




2-CH


3


-4-OCF


3






203






75




CH(CH


3


)CH


2


SO-2-Pyi




3-I




2-CH


3


-4-C


2


F


5






110-111






76




CH(CH


3


)CH


2


SO


2


-2-Pyi




3-I




2-CH


3


-4-i-C


3


F


7






 99-100






77




CH(CH


3


)CH


2


S-n-C


6


H


13






3-I




2-CH


3


-4-OCF


3






Amorphous






78




CH(CH


3


)CH


2


S-n-C


6


H


13






3-I




2-CH


3


-4-i-C


3


F


7






152-153






79




CH(CH


3


)CH


2


SCH


3






3-Br




2-CH


3


-4-i-C


3


F


7






201-202






80




CH(CH


3


)CH


2


SCH


3






3-Br




2-CH


3


-4-OCF


3






195






81




CH(CH


3


)CH


2


SCH


3






3-Br




2-CH


3


-4-C


2


F


5






194-195






82




CH(CH


3


)CH


2


S-c-C


6


H


11






3-I




2-CH


3


-4-OCF


3






166-167






83




CH(CH


3


)CH


2


S-t-C


4


H


9






3-I




2-CH


3


-4-OCF


3






188-189






84




CH(CH


3


)CH


2


S-t-C


4


H


9






3-I




2-CH


3


-4-C


2


F


5






183-184






85




CH(CH


3


)CH


2


S-c-C


6


H


11






3-I




2-CH


3


-4-C


2


F


5






102-103






86




CH(CH


3


)CH


2


S-c-C


6


H


11






3-I




2-CH


3


-4-i-C


3


F


7






95-96






87




CH(CH


3


)CH


2


SOCH


3






3-Br




2-CH


3


-4-OCF


3






212-213






88




CH(CH


3


)CH


2


SO


2


CH


3






3-Br




2-CH


3


-4-OCF


3






 93






89




CH(Ph)CH


2


SCH


3






3-I




2-CH


3


-4-i-C


3


F


7






168-170






90




CH(Ph)CH


2


SCH


3






3-I




2-CH


3


-4-C


2


F


5






157-159






91




CH(Ph)CH


2


SCH


3






3-I




2-CH


3


-4-OCF


3






178-180






92




CH(CH


3


)(CH


2


)


3


SCH


3






3-I




2-CH


3


-4-i-C


3


F


7






160-161






93




CH(CH


3


)(CH


2


)


3


SCH


3






3-I




2-CH


3


-4-C


2


F


5






147-149






94




CH(CH


3


)(CH


2


)


3


SCH


3






3-I




2-CH


3


-4-OCF


3






183-185






95




CH(CH


3


)CH


2


SOCH


3






3-Br




2-CH


3


-4-C


2


F


5






 90






96




CH(CH


3


)CH


2


SO


2


CH


3






3-Br




2-CH


3


-4-C


2


F


5






 95






97




CH(CH


3


)CH


2


SO


2


CH


3






3-Br




2-CH


3


-4-i-C


3


F


7






153-155






98




CH(CH


3


)CH


2


SCH


3






3-Cl




2-CH


3


-4-OCF


3






188-189






99




CH(CH


3


)CH


2


SCH


3






3-Cl




2-CH


3


-4-i-C


3


F


7






202-203






100




CH(CH


3


)CH


2


SO


2


CH


3






3-Cl




2-CH


3


-4-OCF


3






104-105






101




CH(CH


3


)CH


2


SO


2


CH


3






3-Cl




2-CH


3


-4-i-C


3


F


7






155-156






102




CH(CH


3


)CH


2


SO


2


CH


3






3-I




2-Cl-4-OCHFCF


2


O-5




198






103




CH(CH


3


)CH


2


SO


2


CH


3






3-I




2-Cl-4-OCF


2


CHFO-5




195






104




CH(CH


3


)CH


2


SCH


3






3-NO


2






2-CH


3


-4-OCF


3






181






105




CH(CH


3


)CH


2


SCH


3






3-NO


2






2-CH


3


-4-C


2


F


5






190-193






106




CH(CH


3


)CH


2


SCH


3






3-NO


2






2-CH


3


-4-i-C


3


F


7






219






107




CH(CH


3


)CH


2


SCH


3






4-I




2-CH


3


-4-OCF


3






179






108




CH(CH


3


)CH


2


SCH


3






4-I




2-CH


3


-4-C


2


F


5






204






109




CH(CH


3


)CH


2


SCH


3






4-I




2-CH


3


-4-i-C


3


F


7






169-176






110




CH(CH


3


)CH


2


SCH


3






5-I




2-CH


3


-4-OCF


3






127-128






111




CH(CH


3


)CH


2


SCH


3






5-I




2-CH


3


-4-C


2


F


5






143






112




CH(CH


3


)CH


2


SCH


3






5-I




2-CH


3


-4-i-C


3


F


7






189






113




CH(CH


3


)CH


2


SCH


3






3-Cl




2-CH


3


-4-C


2


F


5






189-190






114




CH(CH


3


)CH


2


SO


2


CH


3






3-Cl




2-CH


3


-4-C


2


F


5






84-87






115




CH(CH


3


)CH


2


SCH


3






6-Cl




2-CH


3


-4-C


2


F


5






102-103






116




CH(CH


3


)CH


2


SO


2


CH


3






6-Cl




2-CH


3


-4-C


2


F


5






233-234






117




CH(CH


3


)CH


2


S-t-C


4


H


9






3-I




2-CH


3


-4-i-C


3


F


7






252-256






118




CH(CH


3


)CH


2


SO


2


-2-Pyi




3-I




2-CH


3


-4-C


2


F


5






 95-100






119




CH(CH


3


)CH


2


SO


2


-2-Pyi




3-I




2-CH


3


-4-OCF


3






92-93






120




CH(C


2


H


5


)CH


2


SCH


3






3-I




2-CH


3


-4-i-C


3


F


7






190






121




C(CH


3


)


2


CH


2


SCH


3






3-I




2-CH


3


-4-C


2


F


5






194-196






122




C(CH


3


)


2


CH


2


SCH


3






3-I




2-CH


3


-4-i-C


3


F


7






205-206






123




C(CH


3


)


2


CH


2


SO


2


CH


3






3-I




2-CH


3


-4-C


2


F


5






88-90






124




C(CH


3


)


2


CH


2


SO


2


CH


3






3-1




2-CH


3


-4-i-C


3


F


7






88-90






125




C(CH


3


)


2


CH


2


SOCH


3






3-I




2-CH


3


-4-C


2


F


5






74-76






126




C(CH


3


)


2


CH


2


SOCH


3






3-I




2-CH


3


-4-i-C


3


F


7






90-95






127




CH(C


2


H


5


)(CH


2


)


2


SCH


3






3-I




2-CH


3


-4-C


2


F


5






170






128




CH(C


2


H


5


)(CH


2


)


2


SCH


3






3-I




2-CH


3


-4-OCF


3






175






129




CH(CH


3


)CH


2


SCH


3






3-SCF


3






2-CH


3


-4-C


2


F


5






201-203






130




CH(CH


3


)CH


2


SCH


3






3-SCF


3






2-CH


3


-4-i-C


3


F


7






176-178






131




CH(CH


3


)CH


2


SCH


3






3-SOCF


3






2-CH


3


-4-C


2


F


5






183-185






132




CH(CH


3


)CH


2


SCH


3






3-SOCF


3






2-CH


3


-4-i-C


3


F


7






154






133




CH(CH


3


)(CH


2


)


3


SOCH


3






3-I




2-CH


3


-4-C


2


F


5






135






134




CH(CH


3


)(CH


2


)


3


SO


2


CH


3






3-I




2-CH


3


-4-C


2


F


5






163






135




CH(CH


3


)(CH


2


)


3


SOCH


3






3-I




2-CH


3


-4-i-C


3


F


7






172-175






136




CH(CH


3


)(CH


2


)


3


SO


2


CH


3






3-I




2-CH


3


-4-i-C


3


F


7






204






137




CH(Ph)CH


2


SOCH


3






3-I




2-CH


3


-4-i-C


3


F


7






142






138




CH(Ph)CH


2


SO


2


CH


3






3-I




2-CH


3


-4-i-C


3


F


7






203






139




CH(CH


3


)CH


2


SO


2


-t-C


4


H


9






3-I




2-CH


3


-4-OCF


3






90-92






140




C(CH


3


)


2


CH


2


SCH


3






3-I




2-CH


3


-4-OCF


3






172-173






141




C(CH


3


)


2


CH


2


SOCH


3






3-I




2-CH


3


-4-OCF


3






146-147






142




C(CH


3


)


2


CH


2


SO


2


CH


3






3-I




2-CH


3


-4-OCF


3






86-88






143




CH(CH


3


)CH


2


SOCH


3






3-Cl




2-CH


3


-4-OCF


3






199-200






144




CH(CH


3


)CH


2


SOCH


3






3-Cl




2-CH


3


-4-C


2


F


5






152-155






145




CH(CH


3


)CH


2


SCH


3






3-I




2-CH


3


-4-s-C


4


F


9






120






146




CH(CH


3


)CH


2


SCH


3






3-I




2-CH


3


-4-i-C


3


F


7






210









-5-F






147




CH(CH


3


)CH


2


SCH


3






3-Cl-4-F




2-CH


3


-4-OCF


3






188-190






148




CH(CH


3


)CH


2


SCH


3






3-Cl-4-F




2-CH


3


-4-C


2


F


6






203-204






149




CH(CH


3


)CH


2


SCH


3






3-Cl-4-F




2-CH


3


-4-i-C


3


F


7






226-227






150




CH(CH


3


)(CH


2


)


3


SCH


3






3-Cl




2-CH


3


-4-C


2


F


5






124






151




CH(CH


3


)(CH


2


)


3


SCH


3






6-Cl




2-CH


3


-4-C


2


F


5






Paste






152




CH(CH


3


)(CH


2


)


3


SOCH


3






3-Cl




2-CH


3


-4-C


2


F


5






150






153




CH(CH


3


)(CH


2


)


3


SO


2


CH


3






3-Cl




2-CH


3


-4-C


2


F


5






117






154




CH(CH


3


)(CH


2


)


3


SCH


3






3-Cl




2-CH


3


-4-i-C


3


F


7






125






155




CH(CH


3


)(CH


2


)


3


SCH


3






6-Cl




2-CH


3


-4-i-C


3


F


7






Paste






156




CH(CH


3


)(CH


2


)


3


SO


2


CH


3






3-Cl




2-CH


3


-4-i-C


3


F


7






115






157




CH(CH


3


)CH


2


SCH


3






3-I




2-CH


3


-4-CF


3






187






158




CH(CH


3


)CH


2


SCH


3






3-OCH


2






2-CH


3


-4-C


2


F


5






110








—O-4






159




CH(CH


3


)(CH


2


)


2


SCH


3






3-Cl




2-CH


3


-4-i-C


3


F


7






167-169






160




CH(CH


3


)(CH


2


)


2


SCH


3






3-Cl




2-CH


3


-4-C


2


F


5






169-171






161




CH(CH


3


)(CH


2


)


2


SCH


3






3-Cl




2-CH


3


-4-OCF


3






183-184






162




CH(CH


3


)(CH


2


)


2


SCH


3






3-I




2-CH


3


-4-i-C


3


F


7






192-194






163




CH(CH


3


)(CH


2


)


2


SCH


3






3-I




2-CH


3


-4-C


2


F


5






200-201






164




CH(CH


3


)(CH


2


)


2


SCH


3






3-I




2-CH


3


-4-OCF


3






193-194






165




CH(CH


3


)CH(CH


3


)SCH


3






3-I




2-CH


3


-4-i-C


3


F


7






120






166




CH(CH


3


)CH(CH


3


)SO


2


CH


3






3-I




2-CH


3


-4-i-C


3


F


7






130






167




CH(CH


3


)CH(CH


3


)SC


2


H


5






3-I




2-CH


3


-4-i-C


3


F


7






105






168




CH(CH


3


)CH(CH


3


)SO


2


C


2


H


5






3-I




2-CH


3


-4-i-C


3


F


7






105






169




C(CH


3


)


2


CH


2


SCH


3






3-Cl




2-CH


3


-4-i-C


3


F


7






199-200






170




C(CH


3


)


2


CH


2


SCH


3






3-Br




2-CH


3


-4-i-C


3


F


7






200-201






171




C(CH


3


)


2


CH


2


SO


2


CH


3






3-Cl




2-CH


3


-4-i-C


3


F


7






 86






172




C(CH


3


)


2


CH


2


SOCH


3






3-Cl




2-CH


3


-4-i-C


3


F


7






 90






173




CH(CH


3


)(CH


2


)


4


SCH


3






3-I




2-CH


3


-4-C


2


F


5






156






174




CH(CH


3


)(CH


2


)


4


SCH


3






3-I




2-CH


3


-4-i-C


3


F


7






174






175




CH(CH


3


)(CH


2


)


4


SC


2


H


5






3-I




2-CH


3


-4-C


2


F


5






147






176




CH(CH


3


)(CH


2


)


4


SC


2


H


5






3-I




2-CH


3


-4-i-C


3


F


7






168






177




CH(CH


3


)(CH


2


)


4


SOC


2


H


5






3-I




2-CH


3


-4-C


2


F


5






115






178




CH(CH


3


)(CH


2


)


4


SOC


2


H


5






3-I




2-CH


3


-4-i-C


3


F


7






120






179




CH(CH


3


)(CH


2


)


4


SO


2


C


2


H


5






3-I




2-CH


3


-4-C


2


F


5






131






180




CH(CH


3


)(CH


2


)


4


SO


2


C


2


H


5






3-I




2-CH


3


-4-i-C


3


F


7






145






181




C(CH


3


)


2


CH


2


SO


2


CH


3






3-Br




2-CH


3


-4-i-C


3


F


7






90-93






182




C(CH


3


)


2


CH


2


SOCH


3






3-Br




2-CH


3


-4-i-C


3


F


7






212-213






183




C(CH


3


)


2


CH


2


SC


2


H


5






3-I




2-CH


3


-4-i-C


3


F


7






160-162






184




C(CH


3


)


2


CH


2


SOC


2


H


5






3-I




2-CH


3


-4-i-C


3


F


7






78-82






185




C(CH


3


)


2


CH


2


SC


2


H


5






3-Cl




2-CH


3


-4-i-C


3


F


7






132-134






186




C(CH


3


)


2


CH


2


SO


2


C


2


H


5






3-Cl




2-CH


3


-4-i-C


3


F


7






 68






187




C(CH


3


)


2


CH


2


SC


2


H


5






3-Br




2-CH


3


-4-i-C


3


F


7






169-170






188




CH(CH


3


)CH


2


S(CH


2


)


2


SCH


3






3-I




2-CH


3


-4-i-C


3


F


7






169-171






189




CH(CH


3


)CH


2


S(CH


2


)


2


SCH


3






3-I




2-CH


3


-4-C


2


F


5






135-137






190




CH(CH


3


)CH


2


S(CH


2


)


2


SCH


3






3-I




2-CH


3


-4-OCF


3






159-161






191




CH(CH


3


)CH


2


SCH


3






3-SO


2






2-CH


3


-4-i-C


3


F


7






205-206








—CH


3








192




CH(CH


3


)CH


2


SCH


3






6-SO


2






2-CH


3


-4-i-C


3


F


7






210-212








—CH


3








193




CH(CH


3


)CH


2


SOCH


3






3,4




2-CH


3


-4-OCF


3






198-201








—Cl


2








194




CH(CH


3


)CH


2


SO


2


CH


3






3,4




2-CH


3


-4-OCF


3






165-167








—Cl


2








195




CH(CH


3


)(CH


2


)


2


SOCH


3






3-I




2-CH


3


-4-i-C


3


F


7






123-125






196




CH(CH


3


)(CH


2


)


2


SO


2


CH


3






3-I




2-CH


3


-4-i-C


3


F


7






128-130






197




CH(CH


3


)(CH


2


)


4


SO


2


CH


3






3-I




2-CH


3


-4-C


2


F


5






145






198




CH(CH


3


)(CH


2


)


4


SO


2


CH


3






3-I




2-CH


3


-4-i-C


3


F


7






160






199




CH(CH


3


)(CH


2


)


3


SC


2


H


5






3-I




2-CH


3


-4-C


2


F


5






143






200




CH(CH


3


)(CH


2


)


3


SO


2


C


2


H


5






3-I




2-CH


3


-4-C


2


F


5






117






201




CH(CH


3


)(CH


2


)


3


SC


2


H


5






3-l




2-CH


3


-4-i-C


3


F


7






150






202




CH(CH


3


)(CH


2


)


3


SOC


2


H


5






3-I




2-CH


3


-4-i-C


3


F


7






106






203




CH(CH


3


)(CH


2


)


3


SO


2


C


2


H


5






3-I




2-CH


3


-4-i-C


3


F


7






117






204




Q


1






3-I




2-CH


3


-4-i-C


3


F


7






202






205




Q


2






3-I




2-CH


3


-4-i-C


3


F


7






249






206




CH(CH


3


)CH


2


SCH


2


CH═CH


2






3-I




2-CH


3


-4-i-C


3


F


7






168-175






207




CH


2


CH(CH


3


)SC


2


H


5






3-I




2-CH


3


-4-i-C


3


F


7






150






208




CH


2


CH(CH


3


)SO


2


C


2


H


5






3-I




2-CH


3


-4-i-C


3


F


7






130






209




CH


2


CH(CH


3


)SC


2


H


5






6-1




2-CH


3


-4-i-C


3


F


7






155






210




CH(CH


3


)CH


2


SCH


3






3-OCF


3






2-CH


3


-4-i-C


3


F


7






184-185






211




CH(CH


3


)(CH


2


)


2


SOCH


3






3-Cl




2-CH


3


-4-i-C


3


F


7






Amorphous






212




CH(CH


3


)(CH


2


)


2


SO


2


CH


3






3-Cl




2-CH


3


-4-i-C


3


F


7






108-111






213




CH(CH


3


)(CH


2


)


3


SC


2


H


5






3-Br




2-CH


3


-4-i-C


3


F


7






151






214




CH(CH


3


)(CH


2


)


3


SOC


2


H


5






3-Br




2-CH


3


-4-i-C


3


F


7






159






215




CH(CH


3


)(CH


2


)


3


SO


2


C


2


H


5






3-Br




2-CH


3


-4-i-C


3


F


7






150






216




(S)—C* H(CH


3


)CH


2


SCH


3






3-I




2-CH


3


-4-i-C


3


F


7






212-214






217




(R)-C* H(CH


3


)CH


2


SCH


3






3-I




2-CH


3


-4-i-C


3


F


7






214-216






218




C(CH


3


)


2


CH


2


SOC


2


H


5






3-Br




2-CH


3


-4-i-C


3


F


7






107-110






219




C(CH


3


)


2


CH


2


S-n-C


3


H


7






3-I




2-CH


3


-4-i-C


3


F


7






169-170






220




C(CH


3


)


2


CH


2


SO-n-C


3


H


7






3-I




2-CH


3


-4-i-C


3


F


7






88-90






221




C(CH


3


)


2


CH


2


SO


2


-n-C


3


H


7






3-I




2-CH


3


-4-i-C


3


F


7






88-90






222




CH(CH


3


)CH


2


SCH


3






3-Cl-4




2-CH


3


-4-i-C


3


F


7






122-125








—OCH


3








223




CH(CH


3


)CH


2


SCH


3






3-NO


2






2-CH


3


-4




218









—OCF


2


CHFCF


3








224




CH(CH


3


)CH


2


SCH


3






3-NO


2






2-CH


3


-4-O-(3-




188









Cl-5-CF


3


-2-Pyi






225




C(CH


3


)


2


CH


2


SCH


3






3-I




2-Cl-4-OCF


3






166






226




C(CH


3


)


2


CH


2


SO


2


CH


3






3-I




2-Cl-4-OCF


3






141






227




C(CH


3


)


2


CH


2


SCH


3






3-Br




2-Cl-4-OCF


3






160






228




C(CH


3


)


2


CH


2


SO


2


CH


3






3-Br




2-Cl-4-OCF


3






133






229




C(CH


3


)


2


(CH


2


)


3


SCH


3






3-I




2-CH


3


-4-i-C


3


F


7






164






230




C(CH


3


)


2


(CH


2


)


2


SCH


3






3-I




2-CH


3


-4-i-C


3


F


7






108






231




C(CH


3


)


2


(CH


2


)


2


CH(CH


3


)




3-I




2-CH


3


-4-i-C


3


F


7






151







—SCH


3








232




C(CH


3


)


2


CH


2


SOCH


3






3-Br




2-Cl-4-OCF


3






132






233




CH(CH


3


)CH


2


SCH


3






3-I




2-Cl-4-OCF


3






172






234




CH(CH


3


)CH


2


SO


2


CH


3






3-I




2-Cl-4-OCF


3






168






235




C(CH


3


)


2


CH


2


SC


3


H


7


-n




3-Br




2-CH


3


-4-i-C


3


F


7






162-163






236




C(CH


3


)


2


CH


2


SC


3


H


7


-n




3-Cl




2-CH


3


-4-i-C


3


F


7






149-150






237




C(CH


3


)


2


CH


2


SO


2


C


3


H


7


-n




3-Br




2-CH


3


-4-i-C


3


F


7






176-180






238




C(CH


3


)


2


CH


2


SO


2


C


3


H


7


-n




3-Cl




2-CH


3


-4-i-C


3


F


7






202-203






239




CH


2


CH(CH


3


)SCH


3






3-I




2-CH


3


-4-i-C


3


F


7






200






240




CH


2


CH(CH


3


)SO


2


CH


3






3-I




2-CH


3


-4-i-C


3


F


7






130






241




CH(CH


3


)CH


2


SO


2


CH


3






3-OCF


3






2-CH


3


-4-i-C


3


F


7






226-228






242




C(CH


3


)


2


CH


2


SC


2


H


5






3-I




2-Cl-4-OCF


3






163






243




CH(CH


3


)CH


2


SOCH


3






3,4-Cl


2






2-CH


3


-4-i-C


3


F


7






138-139






244




CH(CH


3


)CH


2


SO


2


CH


3






3 4-Cl


2






2-CH


3


-4-i-C


3


F


7






146-148






245




CH(CH


3


)CH


2


SCH


3






3-CF


3






2-CH


3


-4-i-C


3


F


7






209






246




CH(CH


3


)CH


2


SOCH


3






3-Cl




2-CH


3


-4-i-C


3


F


7






110-112






247




C(CH


3


)


2


CH


2


SC


2


H


5






3-I




2-CH


3


-4-C


2


F


5






188-189






248




C(CH


3


)


2


CH


2


SO


2


C


2


H


5






3-I




2-CH


3


-4-C


2


F


5






120-122






249




C(CH


3


)


2


CH


2


SOC


2


H


5






3-I




2-CH


3


-4-C


2


F


5






125-126






250




C(CH


3


)


2


CH


2


SO


2


C


2


H


5






3-I




2-CH


3


-4-OCF


3






125(Rf = great)






251




C(CH


3


)


2


CH


2


SO


2


C


2


H


5






3-I




2-CH


3


-4-OCF


3






146(Rf = small)






252




C(CH


3


)


2


CH


2


SCH


3






3-OCH


2


O-4




2-CH


3


-4-OCF


3






220






253




CH(CH


3


)CH


2


SOCH


3






3-OCF


3






2-CH


3


-4-i-C


3


F


7






220






254




CH(CH


3


)CH


2


SOCH


3






3-CF


3






2-CH


3


-4-i-C


3


F


7






223






255




CH(CH


3


)CH


2


SO


2


CH


3






3-CF


3






2-CH


3


-4-i-C


3


F


7






199-201






256




CH(CH


3


)(CH


2


)


2


SC


2


H


5






3-Cl




2-CH


3


-4-i-C


3


F


7






110-113






257




CH(CH


3


)(CH


2


)


2


SC


2


H


5






3-I




2-CH


3


-4-i-C


3


F


7






173-174






258




Q


5






3-I




2-CH


3


-4-OCF


3






183






259




Q


6






3-I




2-CH


3


-4-i-C


3


F


7






149






260




CH(CH


3


)CH


2


SOC


2


H


5






3-I




2-CH


3


-4-i-C


3


F


7






 96






261




CH(CH


3


)CH


2


SO


2


C


2


H


5






3-I




2-CH


3


-4-i-C


3


F


7






 98






262




CH(CH


3


)CH


2


SC


2


H


5






3-Br




2-CH


3


-4-i-C


3


F


7






155






263




CH(CH


3


)CH


2


SOC


2


H


5






3-Br




2-CH


3


-4-i-C


3


F


7






 96






264




CH(CH


3


)CH


2


SO


2


C


2


H


5






3-Br




2-CH


3


-4-i-C


3


F


7






135






265




CH(CH


3


)CH


2


SC


2


H


5






3-Cl




2-CH


3


-4-i-C


3


F


7






145






266




CH(CH


3


)CH


2


SOC


2


H


5






3-Cl




2-CH


3


-4-i-C


3


F


7






 92






267




CH(CH


3


)CH


2


SO


2


C


2


H


5






3-Cl




2-CH


3


-4-i-C


3


F


7






135






268




CH(CH


3


)CH


2


SCH


3






3-Br




2-CH


3


-4-CF


3






170-172






269




CH(CH


3


)(CH


2


)


2


SOC


2


H


5






3-I




2-CH


3


-4-i-C


3


F


7






132-134






270




CH(CH


3


)(CH


2


)


2


SO


2


C


2


H


5






3-I




2-CH


3


-4-i-C


3


F


7






108-110






271




CH(CH


3


)CH


2


SC


3


H


7


-n




3-Cl




2-CH


3


-4-i-C


3


F


7






174






272




C(CH


3


)


2


(CH


2


)


2


SC


2


H


5






3-I




2-CH


3


-4-i-C


3


F


7






171






273




Q


7






3-I




2-CH


3


-4-i-C


3


F


7






184






274




CH(CH


3


)(CH


2


)


2


SOC


2


H


5






3-Cl




2-CH


3


-4-i-C


3


F


7






128-130






275




CH(CH


3


)(CH


2


)


2


SO


2


C


2


H


5






3-Cl




2-CH


3


-4-i-C


3


F


7






105-106






276




CH(CH


3


)CH


2


SCH


3






3-Cl




2-CH


3


-4-CF


3






158-160






277




CH(CH


3


)CH


2


SO


2


CH


3






3-Br




2-CH


3


-4-CF


3






118-120






278




C(CH


3


)


2


CH


2


SCH


3






3-OCF


2


O-4




2-CH


3


-4-i-C


3


F


7






182






279




CH(CH


3


)CH


2


S-Pyi




3-I




2-CH


3


-4-i-C


3


F


7






126






280




C(CH


3


)


2


(CH


2


)


3


SC


2


H


5






3-I




2-CH


3


-4-OCF


3






170






281




C(CH


3


)


2


(CH


2


)


3


SCH


3






3-Br,6-Br




2-CH


3


-4-i-C


3


F


7






111










Mixture






282




C(CH


3


)


2


(CH


2


)


3


SC


2


H


5






3-Br,6-Br




2-CH


3


-4-i-C


3


F


7






121










Mixture






283




CH(CH


3


)CH


2


SO


2


CH


3






3-Cl




2-CH


3


-4-CF


3






179-181






284




CH(CH


3


)CH


2


SO


2


CH


3






3-I




2-CH


3


-4-CF


3






196-198






285




CH(CH


3


)CH


2


SCH


2


CF


3






3-I




2-CH


3


-4-i-C


3


F


7






216






286




CH(CH


3


)CH


2


S(CH


2


)


2






3-I




2-CH


3


-4-i-C


3


F


7






158-159







—OCOCF


3








287




CH(CH


3


)CH


2


S—C


3


H


7


-n




3-Br




2-CH


3


-4-i-C


3


F


7






111






288




CH(CH


3


)CH


2


SCH


3






3-OCF


2


O-4




2-CH


3


-4-i-C


3


F


7






196






289




CH(CH


3


)CH


2


SO


2


CH


3






3-OCF


2


O-4




2-CH


3


-4-i-C


3


F


7






223






290




CH(CH


3


)CH


2


SCH


3






3-OCF


2


O-4




2-CH


3


-4-OCF


3






191






291




CH(CH


3


)CH


2


SOCH


3






3-OCF


2


O-4




2-CH


3


-4-OCF


3






187






292




C(CH


3


)


2


CH


2


SCH


3






3-OCF


2


O-4




2-CH


3


-4-OCF


3






205






293




C(CH


3


)


2


CH


2


SO


2


CH


3






3-OCF


2


O-4




2-CH


3


-4-OCF


3






218






294




CH(CH


3


)CH


2


SOCH


2


CF


3






3-I




2-CH


3


-4-i-C


3


F


7






207-209






295




CH(CH


3


)CH


2


SO


2


CH


2


CF


3






3-I




2-CH


3


-4-i-C


3


F


7






220-222






296




CH(CH


3


)CH


2


S(CH


2


)


2


OH




3-I




2-CH


3


-4-i-C


3


F


7






157-159






297




CH(CH


3


)CH


2


S(CH


2


)


2






3-I




2-CH


3


-4-i-C


3


F


7






165-167







—OC


2


H


5








298




.CH


2


SCH


3






H




2-CH


3


-4-i-C


3


F


7






157-159






299




CH(CH


3


)CH


2


S-2-(3,5




3-I




2-CH


3


-4-i-C


3


F


7






147-149







—(CH


3


)


2


-Pym)






300




CH(CH


3


)CH


2


SO-2-(3,5




3-I




2-CH


3


-4-i-C


3


F


7






126-128







—(CH


3


)


2


-Pym)






301




CH(CH


3


)CH


2


SO


2


-2-(3,5




3-I




2-CH


3


-4-i-C


3


F


7






134-136







—(CH


3


)


2


-Pym)






302




CH(CH


3


)CH


2


SC(═S)




3-I




2-CH


3


-4-i-C


3


F


7






Paste







—N(CH


3


)


2








303




CH(CH


3


)CH


2


SCH


3






3-I




2-CH


3


-3-C


2


F


5






223-225






304




CH(CH


3


)CH


2


SCH


3






3-I




2-CH


3


-5-C


2


F


5






215-218






305




CH(CH


3


)CH


2


SCH


3






3-Cl




2-CH


3


-4-CF


3






179-181






306




CH(CH


3


)CH


2


SCH


3






3-Br




2-CH


3


-4-CF


3






176-177






307




CH(CH


3


)CH


2


SCH


3






3-I




2-CH


3


-4-CF


3






184-186






308




CH(CH


3


)CH


2


SCH


3






3-N═C(t-




2-CH


3


-4-i-C


3


F


7






113








C


4


H


9


)O-4






309




CH(CH


3


)CH


2


SC


2


H


5






3-I




2-CH


3


-4-CF


3






193-194






310




C(CH


3


)


2


CH


2


SO


2


CH


3






3-Cl




2-CH


3


-4-CF


3






174-175






311




C(CH


3


)


2


CH


2


SOCH


3






3-Br




2-CH


3


-4-CF


3






85-88






312




C(CH


3


)


2


CH


2


SO


2


CH


3






3-Br




2-CH


3


-4-CF


3






151-153






313




C(CH


3


)


2


CH


2


SOCH


3






3-I




2-CH


3


-4-CF


3






102-104






314




C(CH


3


)


2


CH


2


SO


2


CH


3






3-I




2-CH


3


-4-CF


3






153-155






315




CH(CH


3


)CH


2


S(CH


2


)


2






3-I




2-CH


3


-4-i-C


3


F


7






154-155







—OCH


3








316




CH(CH


3


)CH


2


S(CH


2


)


2






3-I




2-CH


3


-4-i-C


3


F


7






160-162







—CO


2


CH


3








317




CH(CH


3


)CH


2


SO(CH


2


)


2






3-I




2-CH


3


-4-i-C


3


F


7






116-118







—OC


2


H


5








318




CH(CH


3


)CH


2


SO


2


(CH


2


)


2






3-I




2-CH


3


-4-i-C


3


F


7






138-140







—OC


2


H


5








319




CH(CH


3


)CH


2


S-Bzt




3-I




2-CH


3


-4-i-C


3


F


7






179-181






320




C(CH


3


)


2


CH


2


SO


2


CH


3






3-Br




2-CH


3


-4-OCF


3






Crystal






321




C(CH


3


)


2


CH


2


SCH


3






3-Br




2-CH


3


-4-OCF


3






178






322




C(CH


3


)


2


CH


2


SCH


3






3-NO


2






2-CH


3


-4-OCF


3






189






323




C(CH


3


)


2


CH


2


SCH


3






3-NO


2






2-Cl-4-CH


3






204






324




C(CH


3


)


2


CH


2


SCH


3






3-NO


2






2-CH


3


-4-Br




208






325




C(CH


3


)


2


CH


2


SCH


3






3-NO


2






2-CH


3


-4-i-C


3


F


7






234






326




C(CH


3


)


2


CH


2


SCH


3






3-NO


2






2,4-Cl


2






178






327




C(CH


3


)


2


CH


2


SOCH


3






3-NO


2






2-CH


3


-4-i-C


3


F


7






143






328




C(CH


3


)


2


CH


2


SO


2


CH


3






3-NO


2






2-CH


3


-4-i-C


3


F


7






197






329




Q


8






3-I




2-CH


3


-4-i-C


3


F


7






183






330




CH(CH


3


)CH


2


SOCH


3






3-Br




2-CH


3


-4-i-C


3


F


7






118






331




(CH


2


)


2


SH




H




2-CH


3


-4-i-C


3


F


7






170






332




CH(CH


3


)CH


2


SCH


3






4-CH═CH—CH




2-CH


3


-4-i-C


3


F


7






158








═CH-5






333




CH(CH


3


)CH


2


SCH


3






3-CH═CH—CH




2-CH


3


-4-i-C


3


F


7






194








═CH-4






334




CH(CH


3


)CH


2


SOCH


3






3-CH═CH—CH




2-CH


3


-4-i-C


3


F


7






115








═CH-4






335




CH(CH


3


)CH


2


SO


2


CH


3






3-CH═CH—CH




2-CH


3


-4-i-C


3


F


7






121








═CH-4






336




CH(CH


3


)CH


2


SCH


3






3-CH═CH—CH




2-CH


3


-4-OCF


3






186








═CH-4






337




CH(CH


3


)CH


2


SCH


3






3-Br




2-Cl-4-OCF


3






155






338




CH(CH


3


)CH


2


SOCH


3






3-Br




2-Cl-4-OCF


3






174






339




CH(CH


3


)CH


2


SO


2


CH


3






3-Br




2-Cl-4-OCF


3






164






340




CH(CH


3


)CH


2


SO(CH


2


)


2






3-I




2-CH


3


-4-i-C


3


F


7






90-93







—OCH


3








341




CH(CH


3


)CH


2


SO


2


(CH


2


)


2






3-I




2-CH


3


-4-i-C


3


F


7






177-178







—OCH


3








342




CH(CH


3


)CH


2


SO(CH


2


)


2






3-I




2-CH


3


-4-i-C


3


F


7






144-147







—CO


2


CH


3








343




CH(CH


3


)CH


2


SO


2


(CH


2


)


2






3-I




2-CH


3


-4-i-C


3


F


7






201-202







—CO


2


CH


3








344




CH(CH


3


)CH


2


SO-2-Bzt




3-I




2-CH


3


-4-i-C


3


F


7






133-135






345




CH(CH


3


)CH


2


SO


2


-2-Bzt




3-I




2-CH


3


-4-i-C


3


F


7






147-149






346




CH(CH


3


)CH


2


SC


2


H


5






3-OCF


3






2-CH


3


-4-i-C


3


F


7






189-190






347




CH(CH


3


)CH


2


SC


2


H


5






5-OCF


3






2-CH


3


-4-i-C


3


F


7






190-192






348




CH(CH


3


)CH


2


SCH


3






3-CF


3






2-CH


3


-4-i-C


3


F


7






220-221






349




CH(CH


3


)CH


2


SC


2


H


5






3-CF


3






2-CH


3


-4-i-C


3


F


7






200-202






350




(CH


2


)


2


SC(═S)NHC


2


H


5






H




2-CH


3


-4-i-C


3


F


7






129






351




CH(CH


3


)CH


2


SCH


3






3-OCF


2


CF


2


O




2-CH


3


-4-i-C


3


F


7






216








-4






352




CH(CH


3


)CH


2


S-2-Thz




3-I




2-CH


3


-4-i-C


3


F


7






180






353




CH(CH


3


)CH


2


S-2-(5-CH


3






3-I




2-CH


3


-4-i-C


3


F


7






122-124







-1,3,4-Thd)






354




CH(CH


3


)CH


2


S-2-(5-CH


3






6-I




2-CH


3


-4-i-C


3


F


7






148-150







-1,3,4-Thd)






355




C(CH


3


)


2


CH


2


SCH


3






3-OCF


3






2-CH


3


-4-i-C


3


F


7






208-209






356




C(CH


3


)


2


CH


2


SCH


3






5-OCF


3






2-CH


3


-4-i-C


3


F


7






225






357




CH(CH


3


)CH


2


SO


2


C


2


H


5






3-OCF


3






2-CH


3


-4-i-C


3


F


7






219-220






358




C(CH


3


)


2


CH


2


SO


2


CH


3






3-CF


3






2-CH


3


-4-i-C


3


F


7






159-161






359




CH(CH


3


)CH


2


SO


2


C


2


H


5






3-CF


3






2-CH


3


-4-i-C


3


F


7






218-219






360




C(CH


3


)


2


CH


2


SO


2


CH


3






3-OCF


3






2-CH


3


-4-i-C


3


F


7






168-170






361




CH(CH


3


)CH


2


SCH


2


CO




3-I




2-CH


3


-4-i-C


3


F


7






130-131







—N(C


2


H


5


)


2








362




CH(CH


3


)CH


2


SOCH


2


CO




3-I




2-CH


3


-4-i-C


3


F


7






95-98







—N(C


2


H


5


)


2








363




CH(CH


3


)CH


2


SO


2


CH


2


CO




3-I




2-CH


3


-4-i-C


3


F


7






197-199







—N(C


2


H


5


)


2








364




CH(CH


3


)CH


2


SO


2


-2-Thz




3-I




2-CH


3


-4-i-C


3


F


7






153-155






365




C(CH


3


)


2


CH


2


SCH


3






3-I




2-CH


2


OH




188-191









-4-i-C


3


F


7








366




C(CH


3


)


2


CH


2


SCH


3






3-I




2-CH


3


-3-F




218-221









-4-i-C


3


F


7








367




C(CH


3


)


2


CH


2


SCH


3






3-I




2-CH


3


-4-n-C


4


F


9






170-174






368




CH(CH


3


)CH


2


SCH


3






3-I




2-CH


3






203-207









-4-Si(CH


3


)


3








369




C(CH


3


)


2


CH


2


SCH


3






3-Cl




2-Cl-4-OCF


3






154






370




C(CH


3


)


2


CH


2


SOCH


3






3-Cl




2-Cl-4-OCF


3






 73






371




C(CH


3


)


2


CH


2


SO


2


CH


3






3-Cl




2-Cl-4-OCF


3






149






372




CH(CH


3


)CH


2


SCH


3






3-Cl-4-CH


3






2-CH


3


-4-i-C


3


F


7






189






373




C(CH


3


)


2


CH


2


SCH


3






3-NO


2






2-CH


3


-4-C


2


F


5






218






374




C(CH


3


)


2


CH


2


SOCH


3






3-NO


2






2-CH


3


-4-C


2


F


5






194






375




C(CH


3


)


2


CH


2


SO


2


CH


3






3-NO


2






2-CH


3


-4-C


2


F


5






210






376




C(CH


3


)


2


CH


2


SCH


3






3-NO


2






2-Cl-4-OCF


3






181






377




C(CH


3


)


2


CH


2


SOCH


3






3-NO


2






2-Cl-4-OCF


3






185






378




C(CH


3


)


2


CH


2


SO


2


CH


3






3-NO


2






2-Cl-4-OCF


3






186






379




CH(CH


3


)CH


2


SO


2


CH


3






3-Cl-4-CH


3






2-CH


3


-4-i-C


3


F


7






158-159






380




CH(CH


3


)CH


2


SCH


3






3-Cl




2-Cl-4-OCF


3






164






381




CH(CH


3


)CH


2


SOCH


3






3-Cl




2-Cl-4-OCF


3






172






382




CH(CH


3


)CH


2


SO


2


CH


3






3-Cl




2-Cl-4-OCF


3






153






383




CH(CH


3


)CH


2


SSCH


3






3-Cl




2-CH


3


-4-i-C


3


F


7






 92






384




CH(CH


3


)CH


2


SS




3-Cl




2-CH


3


-4-i-C


3


F


7






 91







-(2-NO


2


—Ph)






385




C(CH


3


)


2


CH


2


SCH


3






3-F




2-Cl-4-OCF


3






148






386




C(CH


3


)


2


CH


2


SOCH


3






3-F




2-Cl-4-OCF


3






102






387




C(CH


3


)


2


CH


2


SO


2


CH


3






3-F




2-Cl-4-OCF


3






163






388




CH(CH


3


)CH


2


SOCH


3






3-NO


2






2-CH


3


-4-i-C


3


F


7






218






389




CH(CH


3


)CH


2


SOCH


3






3-NO


2






2-CH


3


-4-OCF


3






218






390




CH(CH


3


)CH


2


SOCH


3






3-NO


2






2-CH


3


-4-CF


3






243






391




CH(CH


3


)CH


2


SOCH


3






3-NO


2






2-CH


3


-4-C


2


F


5






210






392




CH(CH


3


)CH


2


SH




3-I




2-CH


3


-4-i-C


3


F


7






226






393




CH(CH


3


)CH


2


SCH


3






3-I




2-CH


3


-4-OCF


2






192-193









—CHFOCF


3








394




CH(CH


3


)CH


2


SOCH


3






3-I




2-CH


3


-4-OCF


2






206-208









—CHFOCF


3








395




CH(CH


3


)CH


2


SO


2


CH


3






3-I




2-CH


3


-4-OCF


2






166-167









—CHFOCF


3








396




CH(CH


3


)CH


2


SCH


3






3-I




2-CH


3


-4-OCF


2






175-176









—CHFOC


3


F


7


-n






397




CH(CH


3


)CH


2


SCH


3






3-I




2-CH


3


-4-O-(3-Cl




195-197









-5-CF


3


-2-Pyi)






398




C(CH


3


)


2


CH


2


SCH


3






3-I




2-CH


3


-4-O-(3-Cl




180-181









-5-CF


3


-2-Pyi)






399




C(CH


3


)


2


CH


2


SC


3


H


7


-i




3-I




2-CH


3


-4-i-C


3


F


7






85-88






400




C(CH


3


)


2


CH


2


SC


4


H


9


-t




3-I




2-CH


3


-4-i-C


3


F


7






95-98






401




C(CH


3


)


2


CH


2


SOC


4


H


9


-t




3-I




2-CH


3


-4-i-C


3


F


7






100-104






402




C(CH


3


)


2


CH


2


SOC


3


H


7


-i




3-I




2-CH


3


-4-i-C


3


F


7






100-104






403




CH(CH


3


)CH


2


S-2-Pyi




3-Br




2-CH


3


-4-i-C


3


F


7






 93






404




CH(CH


3


)CH


2


SO-2-Pyi




3-Br




2-CH


3


-4-i-C


3


F


7






137






405




CH(CH


3


)CH


2


SO


2


-2-Pyi




3-Br




2-CH


3


-4-i-C


3


F


7






 96






406




C(CH


3


)


2


CH


2


SOCH


3






3-I




2-CH


3


-4-O-(3-Cl




105-108









-5-CF


3


-2-Pyi)






407




C(CH


3


)


2


CH


2


SO


2


CH


3






3-I




2-CH


3


-4-O-(3-Cl




135-136









-5-CF


3


-2-Pyi)






408




CH(CH


3


)CH


2


SOCH


3






3-I




2-CH


3


-4-OCF


2






179-181









—CHFOC


3


F


7


-n






409




CH(CH


3


)CH


2


SO


2


CH


3






3-I




2-CH


3


-4-OCF


2






196-198









—CHFOC


3


F


7


-n






410




CH(CH


3


)CH


2


SOCH


3






3-I




2-CH


3


-4-O-(3-Cl




176-179









-5-CF


3


-2-Pyi)






411




CH(CH


3


)CH


2


SO


2


CH


3






3-I




2-CH


3


-4-O-(3-Cl




199-201









-5-CF


3


-2-Pyi)






412




C(CH


3


)


2


CH


2


SOCH


3






3-I




2-CH


3


-3-F-4-i-C


3


F


7






120-125






413




C(CH


3


)


2


CH


2


SO


2


CH


3






3-I




2-CH


3


-3-F-4-i-C


3


F


7






206-210






414




CH(CH


3


)CH


2


SCH


3






3-Br




2-C


2


H


5


-4-i-C


3


F


7






175






415




CH(CH


3


)CH


2


SCH


3






3-Br




2-Cl-4-C


2


F


5






180






416




CH(CH


3


)CH


2


SCH


3






3-Br




3-I-C


3


H


7






135






417




C(CH


3


)


2


CH


2


SCH


3






3-I




2-CH


3


-4-OSO


2


CF


3






187










Decom-






418




C(CH


3


)


2


CH


2


SCH


3






6-I




2-CH


3


-4-OSO


2


CF


3






posed






419




C(CH


3


)


2


CH


2


SOCH


3






3-I




2-CH


3


-4-OSO


2


CF


3






Amorphous






420




C(CH


3


)


2


CH


2


SCH


3






3-I




2-CH


3


-4-OCF


2






170-172









—CHFOC


3


F


7


-n






421




C(CH


3


)


2


CH


2


SOCH


3






3-I




2-CH


3


-4-OCF


2






68-75









—CHFOC


3


F


7


-n






422




C(CH


3


)


2


CH


2


SO


2


CH


3






3-I




2-CH


3


-4-OCF


2






170-172









—CHFOC


3


F


7


-n






423




C(CH


3


)


2


CH


2


SC


3


H


7


-i




3-Br




2-CH


3


-4-C


2


F


5






162-163






424




C(CH


3


)


2


CH


2


SO


2


C


3


H


7


-i




3-I




2-CH


3


-4-i-C


3


F


7






70-75






425




CH(CH


3


)CH


2


SC(═S)NH




3-I




2-CH


3


-4-i-C


3


F


7






142







—CH


3








426




CH(CH


3


)CH


2


SC(═S)NH




3-I




2-CH


3


-4-i-C


3


F


7






123







—C


2


H


5








427




CH(CH


3


)CH


2


SCONHC


2


H


5






3-I




2-CH


3


-4-i-C


3


F


7






178






428




CH(CH


3


)CH


2


SCOCH


3






3-I




2-CH


3


-4-i-C


3


F


7






117






429




CH(CH


3


)CH


2


SCH


2


C≡CH




3-I




2-CH


3


-4-i-C


3


F


7






111






430




CH(CH


3


)CH


2


SCH


2






3-I




2-CH


3


-4-i-C


3


F


7






140







-(2,4-Cl


2


-Ph)






431




C(CH


3


)


2


CH


2


S* OCH


3






3-I




2-CH


3


-4-i-C


3


F


7






Amorphous







(−)isomer






[α] = −20.4






432




C(CH


3


)


2


CH


2


S* OCH


3






3-I




2-CH


3


-4-i-C


3


F


7






Amorphous







(+)isomer






[α] = 20.6






433




C(CH


3


)


2


CH


2


SCH


3






3-I




3-CF


2


OCF


2


O-4




205






434




C(CH


3


)


2


CH


2


SCH


3






3-I




2-Cl-3-CF


2


OCF


2


O-4




173






435




C(CH


3


)


2


CH


2


SCH


3






3-I




2-C


2


H


5


-4-i-C


3


F


7






188






436




C(CH


3


)


2


CH


2


SOCH


3






3-I




2-C


2


H


5


-4-i-C


3


F


7






125






437




C(CH


3


)


2


CH


2


SO


2


CH


3






3-I




2-C


2


H


5


-4-i-C


3


F


7






166-167






438




C(CH


3


)


2


CH


2


S—Ph




3-I




2-CH


3


-4-i-C


3


F


7






167-168






439




C(CH


3


)


2


CH


2


SO—Ph




3-I




2-CH


3


-4-i-C


3


F


7






107






440




C(CH


3


)


2


CH


2


SO


2


—Ph




3-I




2-CH


3


-4-i-C


3


F


7






200






441




C(CH


3


)


2


CH


2


S-2-Pyi




3-I




2-CH


3


-4-i-C


3


F


7






120-122






442




C(CH


3


)


2


CH


2


SO-




3-I




2-CH


3


-4-i-C


3


F


7






90-95







2-Pyi






443




C(CH


3


)


2


CH


2


SO


2


-




3-I




2-CH


3


-4-i-C


3


F


7






138







2-Pyi






444




C(CH


3


)


2


CH


2


SO


2


-




6-I




2-CH


3


-4-i-C


3


F


7






219







2-Pyi






445




Q


10






3-I




2-CH


3


-4-i-C


3


F


7






212-213






446




Q


11






3-I




2-CH


3


-4-i-C


3


F


7






193-213






447




Q


12






3-I




2-CH


3


-4-i-C


3


F


7






203-205






448




C(CH


3


)


2


CH


2


SCH


3






3-I




2-Cl-4-i-C


3


F


7






184






449




C(CH


3


)


2


CH


2


SOCH


3






3-I




2-Cl-4-i-C


3


F


7






102-105






450




C(CH


3


)


2


CH


2


SO


2


CH


3






3-I




2-Cl-4-i-C


3


F


7






200-201






451




C(CH


3


)


2


CH


2


SCH


2


-




3-I




2-CH


3


-4-i-C


3


F


7






163-164







(4-Cl—Ph)






452




CH(CH


2


OH)(CH


2


)


2


S—




3-I




2-CH


3


-4-i-C


3


F


7






102







CH


3








453




C(CH


3


)


2


CH


2


SCH


3






3-I




2-CH


3


-4-(4-Cl—Ph)




172






454




C(CH


3


)


2


CH


2


SO


2


CH


3






3-I




2-CH


3


-4-(4-Cl—Ph)




128






455




C(CH


3


)


2


CH


2


SCH


3






3-NO


2






2-CH


3


-4-S(2-Cl—Ph)




188






456




C(CH


3


)


2


CH


2


SCH


3






3-NO


2






2-CH


3


-4-S(3-Cl—Ph)




181






457




C(CH


3


)


2


CH


2


SCH


3






3-NO


2






2-CH


3


-4-S(4-Cl—Ph)




201






458




C(CH


3


)


2


CH


2


SCH


3






3-I




2-CH


3


-4-S(2-Cl—Ph)




159






459




C(CH


3


)


2


CH


2


SCH


3






3-I




2-CH


3


-4-S(3-Cl—Ph)




156






460




C(CH


3


)


2


CH


2


SCH


3






3-I




2-CH


3


-4-S(3-Cl—Ph)




156






461




CH(CH


3


)CH


2


SCON—




3-I




2-CH


3


-4-i-C


3


F


7






117







(CH


3


)


2








462




CH(CH


3


)CH


2


SCON—




3-I




2-CH


3


-4-i-C


3


F


7






75







(C


2


H


5


)


2








463




CH(CH


3


)CH


2


SCH


2


CO—




3-I




2-CH


3


-4-i-C


3


F


7






86







CH


3








464




C(CH


3


)


2


CH


2


SCH


3






3-I




2-CH(CH


3


)CH


2


CH—




178









(CH


3


)


2


-4-i-C


3


F


7








465




C(CH


3


)


2


CH


2


SOCH


3






3-I




2-CH(CH


3


)CH


2


CH—




100-105









(CH


3


)


2


-4-i-C


3


F


7








466




C(CH


3


)


2


CH


2


SO


2


CH


3






3-I




2-CH(CH


3


)CH


2


CH—




157-158









(CH


3


)


2


-4-i-C


3


F


7








467




(S)-C* H(CH


3


)CH


2


S




3-I




2-CH


3


-4-i-C


3


F


7






197







—C


2


H


5








468




C(CH


3


)


2


CH


2


SCH


3






3-I




2-CH


3


-4-(CO-(4-




138









CH


3


—Ph))






469




C(CH


3


)


2


CH


2


SCH


3






3-I




2-CH


3


-4-(CO-(4-




171









Cl—Ph))






470




C(CH


3


)


2


CH


2


SCH


3






3-I




2-CH


3


-4-(C(═NOCH


3


)




Paste









—(4-Cl—Ph))






471




C(CH


3


)


2


CH


2


SCH


3






3-I




2-CH


3


-4-CH


2


(4-Cl—




162









Ph)






472




C(CH


3


)


2


CH


2


SCH


3






3-I




2-CH


3


-4-CH(OH)(4-




Paste









Cl—Ph)






473




C(CH


3


)


2


CH


2


SCH


3






3-I




2-CH


3


-4-O(4-Cl—Ph)




179






474




C(CH


3


)


2


CH


2


SCH


3






3-I




2-CH


3


-4-O(3-Cl—Ph)




170






475




C(CH


3


)


2


CH


2


SCH


3






3-I




2-CH


3


-4-O(3-CN—Ph)




176






476




CH(CH


3


)CH


2


SCH


3






3-O(3-




2-CH


3


-4-i-C


3


F


7






169-170








CF


3


—Ph)






477




CH(CH


3


)CH


2


SCH


3






6-O(3-




2-CH


3


-4-i-C


3


F


7






167-169








CF


3


—Ph)






478




C(CH


3


)


2


CH


2


SCH


3






3-I




4-SO


2


N(C


2


H


5


)


2






207-208






479




C(CH


3


)


2


CH


2


SCH


3






3-I




2-CH


3


-4-(CONH(4-Cl—




236









Ph))






480




C(CH


3


)


2


CH


2


SCH


3






3-I




2-CH


3


-4-(CON(CH


3


)-




149









(4-Cl—Ph))






481




C(CH


3


)


2


CH


2


SCH


3






3-I




2-CH


3


-4-C(CF


3


)


2


OCH


3






195-196






482




C(CH


3


)


2


CH


2


SOCH


3






3-I




2-CH


3


-4-C(CF


3


)


2


OCH


3






178-180






483




C(CH


3


)


2


CH


2


SO


2


CH


3






3-I




2-CH


3


-4-C(CF


3


)


2


OCH


3






205-206






484




C(CH


3


)


2


CH


2


SCH


3






3-I




2-CH


3


-4-C(CF


3


)


2







149-151









OCH


2


—Ph






485




C(CH


3


)


2


CH


2


SCH


3






H




4-CF


3






185-188






486




C(CH


3


)


2


CH


2


SCH


3






3-I




2-CH


3


-4-C(CF


3


)


2


OH




143-145






487




C(CH


3


)


2


CH


2


SCH


3






3-I




4-NHSO


2


CF


3






207-209






488




CH(CH


3


)CH


2


SOCH


3






H




4-CF


3






226-227






489




CH(CH


3


)CH


2


SO


2


CH


3






H




4-CF


3






192-194






490




C(CH


3


)


2


CH


2


SCH


3






3-I




2-CH


3


-4-(C(═NOH)-




112









(4-Cl—Ph))






491




C(CH


3


)


2


CH


2


SCH


3






3-I




2-CH


3


-4-C(CF


3


)


2


S—




163-164









CH


3








492




C(CH


3


)


2


CH


2


SOCH


3






3-I




2-CH


3


-4-C(CF


3


)


2


O—




150-152









CH


2


Ph






493




C(CH


3


)


2


CH


2


SO


2


CH


3






3-I




2-CH


3


-4-C(CF


3


)


2


O—




125-126









CH


2


Ph






494




C(CH


3


)


2


CH


2


SCH


3






3-I




2-CH


3


-4-(CON—




187









(C


2


H


5


)


2


)






495




C(CH


3


)


2


CH


2


SCH


3






3-I




2-CH


3


-4-(CON—




Amorphous









(CH


3


)


2








496




C(CH


3


)


2


CH


2


SCH


3






3-I




2-CH


3


-4-(CF


3


)


2


O—




185-186









C


2


H


5








497




C(CH


3


)


2


CH


2


SCH


3






3,4-Cl


2






2-CH


3


-4-i-C


3


F


7








498




C(CH


3


)


2


CH


2


SOCH


3






3,4-Cl


2






2-CH


3


-4-i-C


3


F


7








499




C(CH


3


)


2


CH


2


SO


2


CH


3






3,4-Cl


2






2-CH


3


-4-i-C


3


F


7








500




CH(CH


2


OCH


3


)CH


2


S—




3-I




2-CH


3


-4-i-C


3


F


7









CH


3








501




CH(CH


2


OCH


3


)CH


2







3-I




2-CH


3


-4-i-C


3


F


7









SOCH


3








502




CH(CH


2


OCH


3


)CH


2







3-I




2-CH


3


-4-i-C


3


F


7









SO


2


CH


3








503




CH(CF


3


)CH


2


SCH


3






3-I




2-CH


3


-4-i-C


3


F


7








504




CH(CH


2


SCH


3


)CH


2







3-I




2-CH


3


-4-i-C


3


F


7









COOCH


3








505




CH(CH


2


SCH


3


)CH


2







3-I




2-CH


3


-4-i-C


3


F


7









CONHCH


3








506




CH(CH


2


SCH


3


)CH


2







3-I




2-CH


3


-4-i-C


3


F


7









CON(CH


3


)


2








507




C(CH


3


)


2


CH


2


S—




3-I




2-CH


3


-4-i-C


3


F


7









C


3


H


5


-c






508




C(CH


3


)


2


CH


2


SO—




3-I




2-CH


3


-4-i-C


3


F


7









C


3


H


5


-c






509




C(CH


3


)


2


CH


2


SO


2







3-I




2-CH


3


-4-i-C


3


F


7









C


3


H


5


-c






510




Q


13






3-I




2-CH


3


-4-i-C


3


F


7








511




Q


16






3-I




2-CH


3


-4-i-C


3


F


7








512




Q


14






3-I




2-CH


3


-4-i-C


3


F


7








513




Q


15






3-I




2-CH


3


-4-i-C


3


F


7








514




C(CH


3


)


2


CH


2


SCH


3






3-I




2-CH


3


-4-(4-CF


3


—Ph)






515




C(CH


3


)


2


CH


2


SOCH


3






3-I




2-CH


3


-4-(4-CF


3


—Ph)






516




C(CH


3


)


2


CH


2


SO


2


CH


3






3-I




2-CH


3


-4-(4-CF


3


—Ph)






517




C(CH


3


)


2


CH


2


SCH


3






3-I




2-CH


3


-4-OCF


2


CF


3








518




C(CH


3


)


2


CH


2


SOCH


3






3-I




2-CH


3


-4-OCF


2


CF


3








519




C(CH


3


)


2


CH


2


SO


2


CH


3






3-I




2-CH


3


-4-OCF


2


CF


3








520




C(CH


3


)


2


CH


2


S(═O)—




3-I




2-CH


3


-4-i-C


3


F


7









OCH


3








521




C(CH


3


)


2


CH


2


SO


3


CH


3






3-I




2-CH


3


-4-i-C


3


F


7








522




C(CH


3


)


2


CH


2


SO


2







3-I




2-CH


3


-4-i-C


3


F


7









NHCH


3








523




C(CH


3


)


2


CH


2


SO


2







3-I




2-CH


3


-4-i-C


3


F


7









NHC


2


H


5








524




C(CH


3


)


2


CH


2


SO


2







3-I




2-CH


3


-4-i-C


3


F


7









N(CH


3


)


2








523




C(CH


3


)


2


CH


2


SO


2







3-I




2-CH


3


-4-i-C


3


F


7









N(C


2


H


5


)


2
























TABLE 2











(R


3


= H)





















Property






No




T


1






R2




(X) l




(Y) m




mp (° C.)









2-1




(CH


2


)


2


SC


2


H


5






n-C


3


H


7






H




2-CH


3


-4-i-C


3


F


7






Paste






2-2




(CH


2


)


2


SCH


3






n-C


3


H


7






H




2-CH


3


-4-i-C


3


F


7






122






2-3




(CH


2


)


2


SCH


3






n-C


3


H


7






3-F




2-CH


3


-4-i-C


3


F


7






124






2-4




(CH


2


)


2


SO


2


CH


3






n-C


3


H


7






3-F




2-CH


3


-4-i-C


3


F


7






81






2-5




(CH


2


)


2


SCH


3






C


2


H


5






3-F




2-CH


3


-4-i-C


3


F


7






132-137






2-6




(CH


2


)


3


SCH


3






C


2


H


5






3-F




2-CH


3


-4-i-C


3


F


7






120-122






2-7




(CH


2


)


2


SCH


3






CH


3






3-F




2-CH


3


-4-i-C


3


F


7






127-132






2-8




CH


2


SCH


3






C


2


H


5






3-Cl




2-CH


3


-4-i-C


3


F


7






155-159






2-9




(CH


2


)


2


SOCH


3






CH


3






3-F




2-CH


3


-4-i-C


3


F


7






Paste






2-10




(CH


2


)


2


SO


2


CH


3






CH


3






3-F




2-CH


3


-4-i-C


3


F


7






160-164






2-11




(CH


2


)


2


SOCH


3






C


2


H


5






3-F




2-CH


3


-4-i-C


3


F


7






Paste






2-12




(CH


2


)


2


SO


2


CH


3






C


2


H


5






3-F




2-CH


3


-4-i-C


3


F


7






Paste






2-13




(CH


2


)


3


SOCH


3






C


2


H


5






3-F




2-CH


3


-4-i-C


3


F


7






Paste






2-14




(CH


2


)


3


SO


2


CH


3






C


2


H


5






3-F




2-CH


3


-4-i-C


3


F


7






173






2-15




CH(CH


3


)CH


2






C


2


H


5






3-F




2-CH


3


-4-i-C


3


F


7






114







SCH


3








2-16




CH


2


SCH


3






C


2


H


5






3-Cl




2-CH


3


-4-OCF


3





















Refr.Index nD1.5440










(21.0° C.)






2-17




CH


2


SCH


3






C


2


H


5






3-Cl




2-CH


3


-4-OC


2


F


5












Refr.Index nD1.5365










(21.0° C.)


































TABLE 3











(R


2


= R


3


= H)





















Property







No




T


2






(X)l




(Y)m




mp (° C.)











3-1




Q


3






3-I




2-CH


3


-4-C


2


F


5






163







3-2




Q


3






3-I




2-CH


3


-4-i-C


3


F


7






144







3-3




Q


4






3-I




2-CH


3


-4-OCF


3






173-175







3-4




Q


4






3-I




2-CH


3


-4-C


2


F


5






158-160







3-5




Q


4






3-I




2-CH


3


-4-i-C


3


F


7






186-188







3-6




Q


9






3-I




2-CH


3


-4-i-C


3


F


7






195-197















In Tables 1 to 3, “Ph” means phenyl group; “Pyi” means pyridyl group; “Pym” means pyrimidyl group; “Thz” means thiazolyl group; “Thd” means thiadiazolyl group; “Bzt” means benzothiazolyl group; “c-” means an alicyclic hydrocarbon group; and Q


1


, Q


2


, Q


3


, Q


4


, Q


5


, Q


6


, Q7, Q


8


, Q


9


, Q


10


, Q


11


, Q


12


, Q


13


, Q


14


, Q


15


and Q


16


represent the following compounds:











In Tables 1, 2 and 3, some compounds show a property of paste. The


1


H-NMR data of such compounds are shown in Table 4.















TABLE 4











No






1


H-NMR[CDCl


3


/TMS, δ value (ppm)]













2




0.8-1.4(m. 9H), 2.4(s. 3H), 2.5-2.8(m. 3H), 4.3(m. 1H),








6.2(d. 1H), 7.2-7.5(m. 3H), 7.8(d. 1H), 8.0(d. 1H),








8.4(d. 1H), 8.5(s. 1H).















The agrohorticultural insecticides containing the phthalamide derivative of the general formula (I) or salt thereof of the present invention as an active ingredient are suitable for controlling various insect pests such as agricultural insect pests, forest insect pests, horticultural insect pests, stored grain insect pests, sanitary insect pests, nematodes, etc., which are injurious to paddy rice, fruit trees, vegetables, other crops, flowers and ornamental plants, etc. They have a marked insecticidal effect, for example, on LEPIDOPTERA including summer fruit tortrix (


Adoxophyes orana fasciata


), smaller tea tortrix (Adoxophyes sp.), Manchurian fruit moth (


Grapholita inopinata


), oriental fruit moth (


Grapholita molesta


), soybean pod border (


Leguminivora glycinivorella


), mulberry leafroller (


Olethreutes mori


), tea leafroller (


Caloptilia thevivora


), Caloptilia sp. (


Calopilia zachrysa


), apple leafminer (


Phyllonorycter ringoniella


), pear barkminer (


Spulerrina astaurota


), common white (


Piers rapae crucivora


), tabacco budworm (Heliothis sp.) codling moth (


Laspey resia pomonella


), diamondback moth (


Plutella xylostella


), apple fruit moth (


Argyresthia conjugella


), peach fruit moth (


Carposina niponensis


), rice stem borer (


Chilo suppressalis


), rice leafroller (


Cnaphalocrocis medinalis


), tabacco moth (


Ephestia elutella


), mulberry pyralid (


Glyphodes pyloalis


), yellow rice borer (


Scirpophaga incertulas


), rice skipper (


Parnara guttata


), rice armyworm (


Pseudaletia separata


), pink borer (


Sesamia inferens


), common cutworm (


Spodoptera litura


), beet armyworm (


Spodoptera exigua


), etc.; HEMIPTERA including aster leafhopper (


Macrosteles fascifrons


), green rice leafhopper (


Nephotettix cincticeps


), brown rice planthopper (


Nilaparvata lugens


), whitebacked rice planthopper (


Sogatella furcifera


), citrus psylla (


Diaphorina citri


), grape whitefly (


Aleurolobus taonabae


), sweetpotato whitefly (


Bemisia tabaci


), greenhouse whitefly (


Trialeurodes vaporariorum


), turnip aphid (


Lipaphis erysimi


), green peach aphid (


Myzus persicae


), Indian wax scale (


Ceroplastes ceriferus


), cottony citrus scale (


Pulvinaria aurantii


), camphor scale (


Pseudaonidia duplex


), san Jose scale (


Comstockaspis perniciosa


), arrowhead scale (


Unaspis yanonensis


), etc.; TYLENCHIDA including root-lesion namatode (Pratylenchus sp.), soybean beetle (


Anomala rufocuprea


), Japanese beetle (


Popillia japonica


), tabacco beetle (


Lasioderma serricorne


), powderpost beetle (


Lyctus brunneus


), twenty-eight-spotted ladybird (


Epilachna vigintiotopunctata


), azuki bean weevile (


Callosobruchus chinensis


), vegetable weevile (


Listroderes costirostris


), maize weevile (


Sitophilus zeamais


), boll weevile (


Authonomus gradis gradis


), rice water weevil (


Lissorhoptrus oryzophilus


), cucurbit leaf beetle (


Aulacophora femoralis


), rice leaf beetle (


Oulema oryzae


), striped flea beetle (


Phyllotreta striolata


), pine shoot beetle (


Tomicus piniperda


), Colorado potato beetle (


Leptinotarsa decemlineata


), Mexican bean beetle (


Epilachna varivestis


), corn rootworm (Diabrotica sp.), etc.; DIPTERA including melon fly (


Dacus


(


Zeugodacus


)


cucurbitae


), oriental fruit fly (


Dacus


(


Bactrocera


)


dorsalis


), rice leafminer (


Agnomyza oryzae


), onion maggot (


Delia antigua


), seedcorn maggot (


Delia platura


), soybean pod gall midge (Asphondylia sp.), muscid fly (


Musca domestica


), house mosquito (


Culex pipiens pipiens


), etc.; and TYLENCHIDA including coffer root-lesion nematode (


Pratylenchus coffeae


), potato cyst nematode (


Globodera rostochiensis


), root-knot nematode (Meloidogyne sp.), citrus nematode (


Tylenchulus semipenetrans


), Aphelenchus sp. (


Aphelenchus avenae


),


chrysanthemum foliar


(


Aphelenchoides ritzemabosi


), etc.




The agricultural and horticultural insecticide containing the phthalamide derivative of the general formula (I) or salt thereof of the present invention as an active ingredient has a marked insecticidal effect on the above-exemplified insect pests, sanitary insect pests, and/or nematodes, which are injurious to paddy field crops, upland crops, fruit trees, vegetables, other crops, flowers and ornament plants, and the like. Therefore, the desired effect of the agricultural and horticultural insecticide of the present invention can be obtained by applying the insecticide to paddy field; upland field; crops such as fruits, vegetables, ornament plants and the like; seeds, flowers, stalks, leaves, etc. of plants itself; environments of plant growth such as paddy field water, soil, etc. at a season at which the insect pests, sanitary pests or nematodes are expected to appear, before their appearance or at the time when their appearance is confirmed.




In general, the agricultural and horticultural insecticide of the present invention is used after being prepared into conveniently usable forms according to an ordinary manner for preparation of agrochemicals.




That is, the phthalamide derivative of the general formula (I) or salt thereof and, optionally, an adjuvant are blended with a suitable inert carrier in a proper proportion and prepared into a suitable preparation form such as a suspension, emulsifiable concentrate, soluble concentrate, wettable powder, granules, dust or tablets through dissolution, dispersion, suspension, mixing, impregnation, adsorption or sticking.




The inert carrier used in this invention may be either solid or liquid. As the solid carrier, there can be exemplified soybean flour, cereal flour, wood flour, bark flour, saw dust, powdered tobacco stalks, powdered walnut shells, bran, powdered cellulose, extraction residues of vegetables, powdered synthetic polymers or resins, clays (e.g. kaolin, bentonite, and acid clay), talcs (e.g. talc and pyrophyllite), silica powders or flakes (e.g. diatomaceous earth, silica sand, mica and white carbon, i.e. synthetic, high-dispersion silicic acid, also called finely divided hydrated silica or hydrated silicic acid, some of commercially available products contain calcium silicate as the major component), activated carbon, powdered sulfur, powdered pumice, calcined diatomaceous earth, ground brick, fly ash, sand, calcium carbonate powder, calcium phosphate powder and other inorganic or mineral powders, chemical fertilizers (e.g. ammonium sulfate, ammonium phosphate, ammonium nitrate, urea and ammonium chloride), and compost. These carriers may be used alone or as a mixture thereof.




The liquid carrier is that which itself has solubility or which is without such solubility but is capable of dispersing an active ingredient with the aid of an adjuvant. The following are typical examples of the liquid carrier and can be used alone or as a mixture thereof. Water; alcohols such as methanol, ethanol, isopropanol, butanol and ethylene glycol; ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone, diisobutyl ketone and cyclohexanone; ethers such as ethyl ether, dioxane, Cellosolve, dipropyl ether and tetrahydrofuran; aliphatic hydrocarbons such as kerosene and mineral oils; aromatic hydrocarbons such as benzene, toluene, xylene, solvent naphtha and alkylnaphthalenes; halogenated hydrocarbons such as dichloroethane, chloroform, carbon tetrachloride and chlorobenzene; esters such as ethyl acetate, diisopropyl phthalate, dibutyl phthalate and dioctyl phthalate; amides such as dimethylformamide, diethylformamide and dimethylacetamide; nitriles such as acetonitrile; and dimethyl sulfoxide.




The following are typical examples of the adjuvant, which are used depending upon purposes and used alone or in combination in some cases, or need not to be used at all.




To emulsify, disperse, dissolve and/or wet an active ingredient, a surfactant is used. As the surfactant, there can be exemplified polyoxyethylene alkyl ethers, polyoxyethylene alkylaryl ethers, polyoxyethylene higher fatty acid esters, polyoxyethylene resinates, polyoxyethylene sorbitan mono-laurate, polyoxyethylene sorbitan monooleate, alkylarylsulfonates, naphthalenesulfonic acid condensation products, ligninsulfonates and higher alcohol sulfate esters.




Further, to stabilize the dispersion of an active ingredient, tackify it and/or bind it, there may be used adjuvants such as casein, gelatin, starch, methyl cellulose, carboxymethyl cellulose, gum arabic, polyvinyl alcohols, turpentine, bran oil, bentonite and ligninsulfonates.




To improve the flowabililty of a solid product, there may be used adjuvants such as waxes, stearates and alkyl phosphates.




Adjuvants such as naphthalenesulfonic acid condensation products and polycondensates of phosphates may be used as a peptizer for dispersible products.




Adjuvants such as silicon oils may also be used as a defoaming agent.




The content of the active ingredient may be varied as required and may be chosen in a range of 0.01 to 80% by weight as an active ingredient. In dusts or granules, the suitable content thereof is from 0.01 to 50% by weight. In emulsifiable concentrates or flowable wettable powders, it is also from 0.01 to 50% by weight.




The agricultural and horticultural insecticide of the present invention is used to control a variety of insect pests in the following manner. That is, it is applied to a crop on which the insect pests are expected to appear or a site where the appearance of the insect pests is undesirable, as it is or after being properly diluted with or suspended inwater or the like, in an amount effective for control of the insect pests.




The applying dosage of the agricultural and horticultural insecticide of the present invention is varied depending upon various factors such as a purpose, insect pests to be controlled, a growth state of a plant, tendency of insect pests appearance, weather, environmental conditions, a preparation form, an application method, an application site and an application time. It may be properly chosen in a range of 0.1 g to 10 kg (in terms of the active ingredient) per 10 ares depending upon purposes.




The agricultural and horticultural insecticide of the present invention may be used in admixture with other agricultural and horticultural disease or pest controllers, acaricides, nematicides, bioagrochemicals, etc.; and herbicides, plant growth regulators, manures, etc. depending upon scenes using the present agricultural and horticultural insecticides, in order to expand both spectrum of controllable diseases and insect pest species and the period of time when effective applications are possible or to reduce the dosage.




The agrohorticultural insecticide of the present invention may be applied to the plant seeds or the cultivation mediums for seeding such as soil to be seeded, the mat for raising seedlings, water, etc. by the method of application to rice nursery box, seed powdering, etc. or by the method of seed disinfection. For controlling the pest insects generated on fruit trees, cereals, upland field for vegetables, etc., it is also possible to make a plant absorb the agrohorticultural agent of the present invention by a seed treatment such as powder coating, dipping, etc., irrigation into seedling-raising carrier such as seedling-raising vessel, planting hole, etc. or by treatment of the culture solution for water culture.




EXAMPLES




Next, typical examples of the present invention are presented below. The present invention is by no means limited by these examples.




Example 1




(1-1) Production of N-[4-(1,1,2,3,3,3-Hexafluoropropoxy)-1-methylphenyl]-3-nitrophthalimide




In 30 ml of acetic acid were dissolved 1.93 g of 3-nitrophthalic anhydride and 2.73 g of 4-(1,1,2,3,3,3-hexafluoropropoxy)-1-methylaniline. A reaction was carried out for 3 hours with heating under reflux. After completion of the reaction, the solvent was distilled off under reduced pressure, and the residue was washed with a mixture of ether and hexane, whereby 4.4 g of the objective compound was obtained.




Property: m.p. 121° C.; Yield: 98%.




(1-2) Production of N


1


-[4-(1,1,2,3,3,3-Hexafluoropropoxy)-1-methylphenyl]-N


2


-(1-methyl-2-methylthioethyl)-3-nitrophthalamide (Compound No. 223)




In 10 ml of dioxane was dissolved 0.54 g of N-[4-(1,1,2,3,3,3-hexafluoropropoxy)-1-methylphenyl]-3-nitrophthalimide. Then, 0.25 g of 1-methyl-2-methylthioethylamine and 0.01 g of acetic acid were added to the solution obtained above, and a reaction was carried out for 3 hours with heating under reflux. After completion of the reaction, the solvent was distilled off under reduced pressure, and the residue was purified by column chromatography using 1/1 mixture of hexane and ethyl acetate as an eluent. Thus, 0.45 g of the objective compound having an Rf value of 0.4 to 0.5 was obtained.




Property: m.p. 218° C.; Yield: 68%.




Example 2




(2-1) Production of 3-Fluoro-N-(4-heptafluoroisopropyl-2-methylphenyl)phthalimide




In 10 ml of acetic acid were dissolved 1.33 g of 3-fluorophthalic anhydride and 4-heptafluoroisopropyl-2-methylaniline. A reaction was carried out for 3 hours with heating under reflux. After completion of the reaction, the solvent was distilled off under reduced pressure, and the residue was washed with a mixture of ether and hexane to obtain 3.1 g of the objective compound.




Property: m.p. 155-157° C.; Yield: 97%.




(2-2) Production of N-(Heptafluoroisopropyl-2-methyl-phenyl)phthalimide




In 20 ml of dimethylformamide was dissolved 2.54 g of 3-fluoro-N-(4-heptafluoroisopropyl-2-methylphenyl)-phthalimide. After adding 2.8 g of a 15% aqueous solution of methylmercaptan to the solution obtained above, a reaction was carried out at room temperature for 3 hours with stirring. After completion of the reaction, the reaction solution was poured into water, and the objective product was extracted with ethyl acetate. The extract solution was dried on anhydrous magnesium, the solvent was distilled off under reduced pressure, and the residue was washed with a mixture of ether and hexane. Thus, 2.2 g of the objective compound was obtained.




Property: m.p. 163-165° C.; Yield: 81%.




(2-3) Production of N-(4-Heptafluoroisopropyl-2-methylphenyl)-3-methylsulfonylphthalimide




In 20 ml of dichloromethane was dissolved 0.63 g of N-(4-heptafluoroisopropyl-2-methylphenyl)-3-methylthiophthalimide. While cooling the solution with ice, 0.58 g of m-chloroperbenzoic acid was added and reacted at room temperature. After completion of the reaction, the reaction solution was poured into water, and the objective product was extracted with chloroform. The organic layer was washed with an aqueous solution of sodium thiosulfate and an aqueous solution of potassium carbonate and dried on anhydrous magnesium, the solvent was distilled off under reduced pressure, and the residue was washed with a mixture of ether and hexane. Thus, 0.63 g of the objective compound was obtained.




Property: m.p. 185-187° C.; Yield: 93%.




(2-4) Production of N


1


-(4-Heptafluoroisopropyl-2-methylphenyl)-N


2


-(1-methyl-2-methylthioethyl)-3-methylsulfonylphthalamide (Compound No. 191) and N


1


-(4-Heptafluoroisopropyl-2-methylphenyl)-N


2


-(1-methyl-2-methylthioethyl)-6-methylsulfonylphthalamide (Compound No. 192)




In 10 ml of dioxane was dissolved 0.63 g of N-(4-heptafluoroisopropyl-2-methylphenyl)-3-methylsulfonyl-phthalimide. After adding 0.25 g of 1-methyl-2-methylthioethylamine and 0.01 g of acetic acid to the solution obtained above, a reaction was carried out for 3 hours with heating under reflux. After completion of the reaction, the solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography using 1/1 mixture of hexane and ethyl acetate as an eluent. Thus, 0.42 g of the first objective compound having an Rf value of 0.5 to 0.7 (Compound No. 191) and 0.18 g of the second objective compound having an Rf value of 0.2 to 0.3 (Compound No. 192) were obtained.




Compound No. 191: Property: m.p. 205-206° C.; Yield: 55%.




Compound No. 192: Property: m.p. 210-212° C.; Yield: 24%.




Example 3




(3-1) Production of 3-Iodo-N-(1-methyl-3-methylthiopropyl)-phthalamic Acid




To a suspension of 2.74 g of 3-iodophthalic anhydride in 8 ml of acetonitrile cooled with ice was slowly added dropwise a solution of 1.19 g of 1-methyl-3-methylthiopropylamine in 3 ml of acetonitrile. After completion of the dropping, a reaction was carried out at room temperature for 3 hours with stirring. After completion of the reaction, the deposited crystal was collected by filtration and washed with a small quantity of acetonitrile. Thus, 3.5 g of the objective compound was obtained.




Property: m.p. 148-150° C.; Yield: 89%.




(3-2) Production of 6-Iodo-N-(1-methyl-3-methylthiopropyl)-phthalisoimide




To a suspension of 0.79 g of 3-iodo-N-(1-methyl-3-methylthiopropyl)phthalamic acid in 10 ml of toluene was added 0.63 g of trifluoroacetic anhydride. A reaction was carried out at room temperature for 30 minutes with stirring. After completion of the reaction, the solvent was distilled off under reduced pressure to obtain 0.75 g of a crude objective product, which was used in the subsequent reaction without purification.




(3-3) Production of 6-Iodo-N


1


-(4-heptafluoroisopropyl-2-methylphenyl)-N


2


-(1-methyl-3-methylthiopropyl)phthalamide (Compound No. 162)




In 10 ml of acetonitrile was dissolved 0.75 g of 6-iodo-N-(1-methyl-3-methylthiopropyl)phthalisoimide. After adding 0.55 g of 4-heptafluoroisopropyl-2-methylaniline and 0.01 g of trifluoroacetic acid to the solution obtained above, a reaction was carried out for 3 hours with stirring. After completion of the reaction, the deposited crystal was collected by filtration and washed with a small quantity of cold acetonitrile. Thus, 1.17 g of the objective compound was obtained.




Property: m.p. 192-194° C.; Yield: 90%.




(3-4) Production of 3-Iodo-N


1


-(4-heptafluoroisopropyl-2-methylphenyl)-N


2


-(1-methyl-3-methylsulfenylpropyl)-phthalamide (Compound No. 195)




In 10 ml of dichloromethane was dissolved 0.65 g of 6-iodo-N


1


-(4-heptafluoroisopropyl-2-methylphenyl)-N


2


-(1-methyl-3-methylthiopropyl)phthalamide. After adding 0.18 g of m-chloroperbenzoic acid to the solution obtained above, a reaction was carried out at room temperature for 3 hours. After completion of the reaction, the reaction solution was poured into water, and the objective product was extracted with chloroform. The organic layer was washed with an aqueous solution of sodium thiosulfate and an aqueous solution of potassium carbonate and dried on anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure, and the residue was washed with a mixture of ether and hexane. Thus, 0.61 g of the objective compound was obtained.




Property: m.p. 123-125° C.; Yield: 92%.




(3-5) Production of 3-Iodo-N


1


-(4-heptafluoroisopropyl-2-methylphenyl)-N


2


-(1-methyl-3-methylsulfonylpropyl)-phthalamide (Compound No. 196)




3-Iodo-N


1


-(4-heptafluoroisopropyl-2-methylphenyl)-N


2


-(1-methyl-3-methylsulfenylpropyl)phthalamide (0.4 g) was treated in the same manner as in Example (3-4). Thus, 0.39 g of the objective compound was obtained.




Property: m.p. 128-130° C.; Yield: 95%.




Example 4




(4-1) Production of N-(4-Heptafluoroisopropyl-2-methylphenyl)-3-trifluoromethoxybenzamide




In 50 ml of tetrahydrofuran was dissolved 2.24 g of 3-trifluoromethoxybenzoyl chloride, to which were slowly added dropwise 2.75 g of 4-heptafluoroisopropyl-2-methylaniline and 1.2 g of triethylamine. After completion of the dropping, a reaction was carried out at room temperature for 1 hour. After completion of the reaction, the reaction solution was poured into water, the objective product was extracted with ethyl acetate and dried on anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure, and the residue was washed with a mixture of ether and hexane. Thus, 4.6 g of the objective compound was obtained.




Property: Oily product; Yield: 99%.




(4-2) Production of N-(4-Heptafluoroisopropyl-2-methylphenyl)-3-trifluoromethoxyphthalamic Acid




In 20 ml of tetrahydrofuran was dissolved 2.2 g of N-(4-heptafluoroisopropyl-2-methylphenyl)-3-trifluoromethoxybenzamide. At −70° C., 10 ml of s-butyllithium (0.96 M/L) was slowly added to the above solution and reacted at that temperature for 30 minutes. Then, the cooling bath was removed, and an excessive amount of carbon dioxide was introduced into the reaction solution and reacted at room temperature for 30 minutes. After completion of the reaction, the reaction solution was poured into water and acidified with dilute hydrochloric acid, the objective product was extracted with ethyl acetate and dried on anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure, and the residue was washed with a mixture of ether and hexane. Thus, 2.1 g of the objective compound was obtained.




Property: m.p. 168-172° C.; Yield: 87%.




(4-3) Production of N-(4-Heptafluoroisopropyl-2-methylphenyl)-3-trifluoromethoxyphthalisoimide




To a suspension of 0.46 g of N-(4-heptafluoroisopropyl-2-methylphenyl)-3-trifluoromethoxyphthalamic acid in 10 ml of toluene was added 0.51 g of trifluoroacetic anhydride, and a reaction was carried out at room temperature for 30 minutes. After completion of the reaction, the solvent was distilled off under reduced pressure to obtain 0.49 g of a crude objective product. The product thus obtained was used in the subsequent reaction without purification.




(4-4) Production of N


1


-(4-Heptafluoroisopropyl-2-methylphenyl)-N


2


-3-(1-methyl-2-methylthioethyl)-3-trifluoromethoxyphthalamide (Compound No. 210)




In 10 ml of acetonitrile was dissolved 0.44 g of N-(4-heptafluoroisopropyl-2-methylphenyl)-3-trifluoromethoxyphthalisoimide. Then, 0.10 g of 1-methyl-2-methylthioethylaniline and 0.01 g of trifluoroacetic acid were added to the solution obtained above, and reacted for 3 hours. After completion of the reaction, the reaction solution was cooled to 0° C., the deposited crystal was collected by filtration, and washed with hexane. Thus, 0.46 g of the objective compound was obtained.




Property: m.p. 184-185° C.; Yield: 77%.




Next, typical formulation examples of the present invention and test examples are presented below. The present invention is by no means limited by these examples.




In the formulation examples, the term “parts” means “parts by weight”.




Formulation Example 1





















Each compound listed in Table 1, 2 or 3




50 parts







Xylene




40 parts







Mixture of polyoxyethylene nonylphenyl




10 parts







ether and calcium alkylbenzenesulfonate















An emulsifiable concentrate was prepared by mixing uniformly the above ingredients to effect dissolution.




Formulation Example 2





















Each compound listed in Table 1, 2 or 3




 3 parts







Clay powder




82 parts







Diatomaceous earth powder




15 parts















A dust was prepared by mixing uniformly and grinding the above ingredients.




Formulation Example 3






















Each compound listed Table 1, 2 or 3




5




parts







Mixed powder of bentonite and clay




90




parts







Calcium lignin sulfonate




5




parts















Granules were prepared by mixing the above ingredients uniformly, and kneading the resulting mixture together with a suitable amount of water, followed by granulation and drying.




Formulation Example 4





















Each compound listed in Table 1, 2 or 3




20 parts







Mixture of kaolin and synthetic




75 parts







high-dispersion silicic acid







Mixture of polyoxyethylene nonylphenyl




 5 parts







ether and calcium alkylbenzenesulfonate















A wettable powder was prepared by mixing uniformly and grinding the above ingredients.




Test Example 1




Insecticidal Effect on Diamond Back Moth (


Plutella xylostella


)




Adult diamondback moths were released and allowed to oviposit on a Chinese cabbage seedling. Two days after the release, the seedling having the eggs deposited thereon was immersed for about 30 seconds in a liquid chemical prepared by diluting a preparation containing each compound listed in Table 1, 2 or 3 as an active ingredient to adjust the concentration to 50 ppm. After air-dryness, it was allowed to stand in a room thermostatted at 25° C. Six days after the immersion, the hatched insects were counted. The mortality was calculated according to the following equation and the insecticidal effect was judged according to the criterion shown below. The test was carried out with triplicate groups of 10 insects.

























Corrected





mortality






(
%
)





=




[





Number





of











hatched





insects





in











untreated





group





]

-

[





Number





of











hatched





insects











in





treated





group





]



[





Number





of











hatched





insects





in











untreated





group





]


×
100




















Criterion:














Effect




Mortality (%)











A




100







B




99-90







C




89-80







D




79-50















The results obtained are shown in Table 5.




Test Example 2




Insecticidal Effect on Common Cutworm (


Spodoptera Litura


)




A piece of cabbage leaf (cultivar; Shikidori) was immersed for about 30 seconds in a liquid chemical prepared by diluting a preparation containing each compound listed in Table 1, 2 or 3 as an active ingredient to adjust the concentration to 50 ppm. After air-dryness, it was placed in a plastic Petri dish with a diameter of 9 cm and inoculated with second-instar larvae of common cutworm, after which the dish was closed and then allowed to stand in a room thermostatted at 25° C. Eight days after the inoculation, the dead and alive were counted. The mortality was calculated according to the following equation and the insecticidal effect was judged according to the criterion shown in Test Example 1. The test was carried out with triplicate groups of 10 insects.







Corrected
mortality  (%)


=




[





Number





of





alive











larvae





in






untreated





group




]

-

[





Number





of





alive











larvae





in






treated





group




]



[




Number





of





alive





larvae






in





untreated











group




]


×
100











The results are shown in Table 5.




Test Example 3




Insecticidal Effect on Smaller tea Tortrix (Adoxophyes sp.)




A leaf of tea tree was immersed for 30 seconds in a liquid chemical containing each compound listed in Table 1, 2 or 3 as an active ingredient to adjust the concentration to 50 ppm. After air-dryness, the leaf was transferred to a plastic dish with a diameter of 9 cm and inoculated with larval smaller tea tortrix. Then, the leaf was allowed to stand in a room thermostatted at 25° C. at a humidity of 70%. Eight days after the inoculation, the dead and alive were counted, and the insecticidal effect was judged according to the same criterion as mentioned in Test Example 1. The test was carried out with triplicate groups of 10 insects.




The results are shown in Table 5.















TABLE 5










Test




Test




Test






No




Example 1




Example 2




Example 3


























1




A




A




A






2




A




A




A






3




A




A




A






4




A






5




A




A






6




A




A




A






7




A




A




A






8




A





C






9




A






10




A




A




A






11




A




A




A






12




A






13




A






14




A






15




A






16




A





A






17




A




A




A






18




A




A




A






19




A




A




A






20




A




A




A






21




A




A




A






22




A




A




A






23




A




A




A






24




A





A






25




A




A




A






26




A




A




A






27




A






28




A




A




A






29




A




A




A






30




A




A




A






31




A




A




A






32




A




A




A






33




A




A




A






34




A




A




A






35




A




A




A






36




A






37




A




A




A






38




A





A






39




A




A




A






41




A




A




A






42




A






43




A





A






44




A





A






46




A





A






47




A






48




A




A




A






49




A




A




A






50




A




A




A






51




A






52




A






53




A





A






54




A




C




A






55




A






56




A




A




A






57




A





A






58




A






59




A





A






60




A





A






61




A




A




A






62




A




A




A






63




A





A






64




A





A






65




A




A




A






66




A




A




A






67




A




A




A






71




A






72




A





A






73




A




C




A






74




A




D






75




A




A




A






76




A




A




A






77




A






78




A






79




A




A




A






80




A




A




A






81




A




A




A






82




A





A






83




A




A




A






84




A




A




A






85




A





A






86




A




A




A






87




A




C






88




A




C






89




A





A






90




A





A






92




A




A




A






93




A




A




A






94




A




A




A






95




A




A




A






96




A




A




A






97




A




A




A






98




A




A




A






99




A




A




A






100




A




C




A






101




A




A




A






102




A




A






103




A






104




A






105




A





A






106




A




A




A






107




A






108




A




A






109




A




A




A






110




A






111




A





B






112




A




A




A






113




A




A




A






114




A




A




A






115




A




A






116




A






117




A





A






118




A




A




A






119




A




A




A






120




A






121




A




A




A






122




A




A




A






123




A




A




A






124




A




A




A






125




A




A




A






126




A




A




A






127




A




A




A






129




A






130




A




A




A






132




A






133




A




A






134




A




A




A






135




A




A




A






136




A




A




A






137




A





A






139




A




A






140




A




A




A






141




A




A






142




A




A




A






143




A




D






144




A




A






145




A




A




A






146




A




A




A






147




A






148




A




C






149




A




A






150




A




A




A






151




A






152




A






153




A




A




A






154




A




A




A






155




A





A






156




A




A




A






157




A




A




A






158




A






159




A




A




A






160




A




A




A






161




A




A




A






162




A




A




A






163




A




A




A






164




A





A






165




A




A




A






166




A




A




A






167




A




A




A






168




A




A




A






169




A




A




A






170




A




A




A






171




A





A






172




A






173




A




A




A






174




A




C




A






175




A




D




A






176




A




A




A






177




A






178




A




D




A






179




A





A






180




A





A






181




A




A




A






182




A




A




A






183




A




A




A






184




A




A




A






185




A




A




A






186




A




A




A






187




A




A




A






188




A




A




A






189




A




A




A






190




A





A






191




A




A






192




A






193




A




D






194




A






195




A




A




A






196




A




A




A






197




A




C




A






198




A




A




A






199




A




A




A






200




A




A




A






201




A




A




A






202




A





A






203




A




A




A






204




A




A




A






205




A




A




A






206




A




A




A






207




A




A




A






208




A




A




A






209




A






210




A




A




A






211




A




A




A






212




A




A




A






213




A




A




A






214




A






215




A





A






216




A




A




A






217




A




A




A






218




A




A




A






219




A




A




A






220




A




A




A






221




A




A




A






222




A






223




A






224




A





A






225




A




A




A






226




A




A




A






227




A




A






228




A




A






229




A




A




A






230




A




A




A






231




A




A




A






232




A




A






233




A




A






234




A




A




A






235




A




A




A






236




A




A




A






237




A




A




A






238




A




A




A






239




A




A




A






240




A




A




A






241




A




A




A






242




A




A




A






243




A




A




A






244




A




A




A






245




A




A




A






246




A




A




A






247




A




A




A






248




A




A




A






249




A




A




A






250




A




A






251




A





A






252




A





A






253




A




A




A






254




A




A




A






255




A




A




A






256




A




A




A






257




A




A




A






258




A






259




A




A




A






260




A




A




A






261




A




A




A






262




A




A




A






263




A




A




A






264




A




A




A






265




A




A




A






266




A




A




A






267




A




A




A






268




A




A




A






269




A




A




A






270




A




A




A






271




A




C




A






272




A




A




A






273




A





C






274




A




C




A






275




A






276




A




A




A






277




A






278




A




A




A






279




A





C






280




A




C




A






281




A




A




A






282




A




A




A






283




A




A




A






284




A




A




A






285




A




A




A






286




A




C




A






287




A




A




A






288




A




A




A






289




A






290




A




D






292




A






293




A





A






294




A




A




A






295




A




A




A






296




A




A




A






297




A




A




A






298




A





A






299




A




D




A






300




A






301




A





A






302




A





A






303




A




A




A






305




A




A




A






306




A




A




A






307




A




A






309




A




A




A






310




A




A




A






311




A




A






312




A




A




A






313




A




A




A






314




A




A




A






315




A




A




A






316




A




A




A






317




A




A




A






318




A




A




A






319




A





A






320




A




C




D






321




A




A




A






322




A






324




A






325




A




A




A






326




A





A






327




A





A






328




A




A




A






329




A





A






330




A




A




A






332




A





A






333




A




A




A






334




A





A






335




A





D






336




A




C




A






337




A




A






338




A




A






339




A




A




A






340




A




A






341




A




A




A






342




A






343




A






344




A





A






345




A






346




A




A




A






347




A






348




A




A




A






349




A




A




A






351




A




A




A






352




A





A






353




A





A






355




A




A




A






356




A






357




A




A




A






358




A




A




A






359




A




A




A






360




A




A




A






361




A




A




A






362




A




A




A






363




A




A




A






364




A




A




A






365




A




A




A






366




A




A




A






367




A




A




A






368




A





A






369




A




A




A






370




A




A






371




A




A




A






372




A




A




A






373




A




A




A






374




A




A




A






375




A




A






376




A




C




A






377




A






378




A






379




A






380




A




A




A






381




A




A






382




A




A




A






383




A




A




A






384




A




D




A






385




A




C






386




A






387




A






388




A




A




A






389




A






390




A






391




A






392




A




D




A






393




A




A




A






394




A




A




A






395




A




A




A






396




A




A




A






397




A




A




A






398




A




A




A






399




A




A




A






400




A




A




A






401




A




A




A






402




A




A




A






403




A




A




A






404




A




A




A






405




A




A




A






406




A




A




A






407




A




A




A






408




A




A




A






409




A




A




A






410




A




A






411




A




A




A






412




A




A




A






413




A




A




A






414




A




A




A






415




A




A




A






417




A




A




A






419




A




A




A






420




A




A




A






421




A




A




A






422




A




A




A






423




A




A




A






424




A




A




B






425




A




A






426




A




D




C






427




A




A




C






428




A




D




A






429




A




A




A






430




A




A




A






431




A




A




A






432




A




A




A






433




A




A




A






434




A




A




A






435




A




A




A






436




A




A




A






437




A




A




A






438




A




A




A






439




A




A




A






440




A




A




A






441




A




A




A






442




A




A




A






443




A




A




A






444




A




D




A






445




A





A






446




A






447




A






448




A




A




A






449




A




A




A






450




A




A




A






451




A





A






452




A






453




A




A




A






454




A




A




A






459




A






460




A




A




D






461




A





D






462




A




D




A






463




A




A




A






465




A






467




A




A




A






469




A






470




A




C




A






471




A





A






472




A





A






473




A





B






474




A





D






475




A





A






478




A






480




A





A






481




A




A




A






482




A




A




A






483




A




A




A






484




A




A




A






486




A




A




A






490




A




C




A






491





















492





















493





















494





















495





















496





















2-3




A





A






2-5




A




C






2-6




A




D






2-7




A






2-8




A




A






2-9




A






 2-10




A




D




A






 2-11




A






 2-12




A





A






 2-13




A





A






 2-14




A




C




A






 2-15




A




A




A






 2-16




A






 2-17




A




A






3-1




A




A






3-2




A













Claims
  • 1. A phthalamide derivative represented by the following general formula (I) or salt thereof: wherein A1 represents C1-C8 alkylene group, substituted C1-C8 alkylene group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group, halo C1-C6 alkylsulfonyl group, hydroxy C1-C6 alkyl group, C1-C6 alkoxy C1-C6 alkyl group, C1-C6 alkylthio C1-C6 alkyl group, C1-C6 alkoxycarbonyl group, phenyl group and substituted phenyl group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group, halo C1-C6 alkylsulfonyl group, mono C1-C6 alkylamino group, di C1-C6 alkylamino group in which C1-C6 alkyl groups may be same or different, and C1-C6 alkoxycarbonyl group, C3-C8 alkenylene group, substituted C3-C8 alkenylene group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group, halo C1-C6 alkylsulfonyl group, C1-C6 alkylthio C1-C6 alkyl group, C1-C6 alkoxycarbonyl group, phenyl group and substituted phenyl group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group, halo C1-C6 alkylsulfonyl group, mono C1-C6 alkylamino group, di C1-C6 alkylamino group in which C1-C6 alkyl groups may be same or different, and C1-C6 alkoxycarbonyl group, C3-C8 alkynylene group, or substituted C3-C8 alkynylene group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group, halo C1-C6 alkylsulfonyl group, C1-C6 alkylthio C1-C6 alkyl group, C1-C6 alkoxycarbonyl group, phenyl group and substituted phenyl group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group, halo C1-C6 alkylsulfonyl group, mono C1-C6 alkylamino group, di C1-C6 alkylamino group in which C1-C6 alkyl groups may be same or different, and C1-C6 alkoxycarbonyl group,further, an arbitrary saturated carbon atom in said C1-C8 alkylene group, substituted C1-C8 alkylene group, C1-C8 alkenylene group, substituted C3-C8 alkenylene group, C3-C8 alkynylene group and substituted C3-C8 alkynylene group may be substituted with a C2-C5 alkylene group to form a C3-C6 cycloalkane ring, and arbitrary two carbon atoms in said C1-C8 alkylene group, substituted C1-C8 alkylene group, C3-C8 alkenylene group and substituted C3-C8 alkenylene group may be taken conjointly with an alkylene group or an alkenylene group to form a C3-C6 cycloalkane ring or C3-C6 cycloalkene ring; R1 represents hydrogen atom, mercapto group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C3-C6 cycloalkyl group, halo C3-C6 cycloalkyl group, phenyl group, substituted phenyl group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group, halo C1-C6 alkylsulfonyl group, mono C1-C6 alkylamino group, di C1-C6 alkylamino group in which C1-C6 alkyl groups may be same or different, and C1-C6 alkoxycarbonyl group, phenylthio group, substituted phenylthio group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group, halo C1-C6 alkylsulfonyl group, mono C1-C6 alkylamino group, di C1-C6 alkylamino group in which C1-C6 alkyl groups may be same or different, and C1-C6 alkoxycarbonyl group, heterocyclic group, substituted heterocyclic group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group, halo C1-C6 alkylsulfonyl group, mono C1-C6 alkylamino group, di C1-C6 alkylamino group in which C1-C6 alkyl groups may be same or different, and C1-C6 alkoxycarbonyl group, or —A2—R4 [wherein A2 represents —C(═O)—, —C(═S)—, or —C(═NR5)— (in which R5 represents hydrogen atom, C1-C6 alkyl group, C1-C6 alkoxy group, mono C1-C6 alkylamino group, di C1-C6 alkylamino group in which C1-C6 alkyl groups may be same or different, C1-C6 alkoxycarbonyl group, phenyl group or substituted phenyl group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group, halo C1-C6 alkylsulfonyl group, mono C1-C6 alkylamino group, di C1-C6 alkylamino group in which C1-C6 alkyl groups may be same or different, and C1-C6 alkoxycarbonyl group), C1-C8 alkylene group, halo C1-C8 alkylene group, C3-C6 alkenylene group, halo C3-C6 alkenylene group, C3-C6 alkynylene group or halo C3-C6 alkynylene group; and (1) in cases where A2 represents —C(═O)—, —C(═S)— or —C(═NR5)— wherein R5 is as defined above, R4 represents hydrogen atom, C1-C6 alkyl group, halo C1-C6 alkyl group, C3-C6 cycloalkyl group, halo C3-C6 cycloalkyl group, phenyl group, substituted phenyl group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group, halo C1-C6 alkylsulfonyl group, mono C1-C6 alkylamino group, di C1-C6 alkylamino group in which C1-C6 alkyl groups may be same or different, and C1-C6 alkoxycarbonyl group, heterocyclic group, substituted heterocyclic group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group, halo C1-C6 alkylsulfonyl group, mono C1-C6 alkylamino group, di C1-C6 alkylamino group in which C1-C6 alkyl groups may be same or different, and C1-C6 alkoxycarbonyl group, or —Z1—R6 wherein Z1 represents —O—, —S— or —N(R7)— (wherein R7 represents hydrogen atom, C1-C6 alkyl group, C1-C6 alkylcarbonyl group, halo C1-C6 alkylcarbonyl group or C1-C6 alkoxycarbonyl group), and R6 represents hydrogen atom, C1-C6 alkyl group, halo C1-C6 alkyl group, C3-C6 alkenyl group, halo C3-C6 alkenyl group, C3-C6 alkynyl group, halo C3-C6 alkynyl group, C3-C6 cycloalkyl group, phenyl group, substituted phenyl group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group, halo C1-C6 alkylsulfonyl group, mono C1-C6 alkylamino group, di C1-C6 alkylamino group in which C1-C6 alkyl groups may be same or different, and C1-C6 alkoxycarbonyl group, phenyl C1-C4 alkyl group, substituted phenyl C1-C4 alkyl group having, on the ring thereof, at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group, halo C1-C6 alkylsulfonyl group, mono C1-C6 alkylamino group, di C1-C6 alkylamino group in which C1-C6 alkyl groups may be same or different, and C1-C6 alkoxycarbonyl group, heterocyclic group, or substituted heterocyclic group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group, halo C1-C6 alkylsulfonyl group, mono C1-C6 alkylamino group, di C1-C6 alkylamino group in which C1-C6 alkyl groups may be same or different, and C1-C6 alkoxycarbonyl group, and (2) in cases where A2 represents C1-C8 alkylene group, halo C1-C8 alkylene group, C3-C6 alkenylene group, halo C3-C6 alkenylene group, C3-C6 alkynylene group or halo C3-C6 alkynylene group, R4 represents hydrogen atom, halogen atom, cyano group, nitro group, C3-C6 cycloalkyl group, halo C3-C6 cycloalkyl group, C1-C6 alkoxycarbonyl group, mono C1-C6 alkylaminocarbonyl group, di C1-C6 alkylaminocarbonyl group in which C1-C6 alkyl groups may be same or different, phenyl group, substituted phenyl group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group, halo C1-C6 alkylsulfonyl group, mono C1-C6 alkylamino group, di C1-C6 alkylamino group in which C1-C6 alkyl groups may be same or different, and C1-C6 alkoxycarbonyl group, heterocyclic group, substituted heterocyclic group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group, halo C1-C6 alkylsulfonyl group, mono C1-C6 alkylamino group, di C1-C6 alkylamino group in which C1-C6 alkyl groups may be same or different, and C1-C6 alkoxycarbonyl group, or —Z2—R8 wherein Z2 represents —O—, —S—, —SO—, —SO2—, —N(R9)— (wherein R9 represents hydrogen atom, C1-C6 alkyl group, C1-C6 alkylcarbonyl group, halo C1-C6 alkylcarbonyl group, C1-C6 alkoxycarbonyl group, phenylcarbonyl group, or substituted phenylcarbonyl group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group and halo C1-C6 alkylsulfonyl group), —C(═O)— or —C(═NOR10)— (wherein R10 represents hydrogen atom, C1-C6 alkyl group, halo C1-C6 alkyl group, C3-C6 alkenyl group, halo C3-C6 alkenyl group, C3-C6 alkynyl group, halo C3-C6 alkynyl group, C3-C6 cycloalkyl group, phenyl C1-C4 alkyl group or substituted phenyl C1-C4 alkyl group having, on the ring thereof, at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group, halo C1-C6 alkylsulfonyl group, mono C1-C6 alkylamino group, di C1-C6 alkylamino group in which C1-C6 alkyl groups may be same or different, and C1-C6 alkoxycarbonyl group) and R8 represents hydrogen atom, C1-C6 alkyl group, halo C1-C6 alkyl group, C3-C6 alkenyl group, halo C3-C6 alkenyl group, C3-C6 alkynyl group, halo C3-C6 alkynyl group, C3-C6 cycloalkyl group, C1-C6 alkylcarbonyl group, halo C1-C6 alkylcarbonyl group, C1-C6 alkoxycarbonyl group, mono C1-C6 alkylaminocarbonyl group, di C1-C6 alkylaminocarbonyl group in which C1-C6 alkyl groups may be same or different, phenyl group, substituted phenyl group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group, halo C1-C6 alkylsulfonyl group, mono C1-C6 alkylamino group, di C1-C6 alkylamino group in which C1-C6 alkyl groups may be same or different, and C1-C6 alkoxycarbonyl group, phenyl C1-C4 alkyl group, substituted phenyl C1-C4 alkyl group having, on the ring thereof, at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group, halo C1-C6 alkylsulfonyl group, mono C1-C6 alkylamino group, di C1-C6 alkylamino group in which C1-C6 alkyl groups may be same or different, and C1-C6 alkoxycarbonyl group, heterocyclic group, or substituted heterocyclic group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group, halo C1-C6 alkylsulfonyl group, mono C1-C6 alkylamino group, di C1-C6 alkylamino group in which C1-C6 alkyl groups may be same or different, and C1-C6 alkoxycarbonyl group], or alternatively, R1 may be combined with A1 to form a 5- to 8-membered ring which may be intercepted by 1 or 2, same or different oxygen atoms, sulfur atoms or nitrogen atoms; R2 and R3 which may be same or different, represent hydrogen atom, C3-C6 cycloalkyl group or —A2—R4 wherein A2 and R4 are as defined above; or alternatively, R2 may be combined with A1 or R1 to form a 5- to 7-membered ring which may be intercepted by 1 or 2, same or different oxygen atoms, sulfur atoms or nitrogen atoms; X which may be same or different, represents halogen atom, cyano group, nitro group, C3-C6 cycloalkyl group, halo C3-C6 cycloalkyl group, C1-C6 alkoxycarbonyl group, phenyl group, substituted phenyl group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group, halo C1-C6 alkylsulfonyl group, mono C1-C6 alkylamino group, di C1-C6 alkylamino group in which C1-C6 alkyl groups may be same or different, and C1-C6 alkoxycarbonyl group, heterocyclic group, substituted heterocyclic group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkyl sulfinyl group, C1-C6 alkylsulfonyl group, halo C1-C6 alkylsulfonyl group, mono C1-C6 alkylamino group, di C1-C6 alkylamino group in which C1-C6 alkyl groups may be same or different, and C1-C6 alkoxycarbonyl group, or —A3—R11 [wherein A3 represents —O—, —S—, —SO—, —SO2—, —C(═O)—, —C(═NOR12)— (in which R12 represents hydrogen atom, C1-C6 alkyl group, halo C1-C6 alkyl group, C3-C6 alkenyl group, halo C3-C6 alkenyl group, C3-C6 alkynyl group, C3-C6 cycloalkyl group, phenyl C1-C4 alkyl group or substituted phenyl C1-C4 alkyl group having, on the ring thereof, at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group, halo C1-C6 alkylsulfonyl group, mono C1-C6 alkylamino group, di C1-C6 alkylamino group in which C1-C6 alkyl groups may be same or different, and C1-C6 alkoxycarbonyl group), C1-C6 alkylene group, halo C1-C6 alkylene group, C2-C6 alkenylene group, halo C2-C6 alkenylene group, C2-C6 alkynylene group or halo C3-C6 alkynylene group; and (1) in cases where A3 represents —O—, —S—, —SO— or —SO2—, R11 represents halo C3-C6 cycloalkyl group, halo C3-C6 cycloalkenyl group, phenyl group, substituted phenyl group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group, halo C1-C6 alkylsulfonyl group, mono C1-C6 alkylamino group, di C1-C6 alkylamino group in which C1-C6 alkyl groups may be same or different, and C1-C6 alkoxycarbonyl group, heterocyclic group, substituted heterocyclic group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group, halo C1-C6 alkylsulfonyl group, mono C1-C6 alkylamino group, di C1-C6 alkylamino group in which C1-C6 alkyl groups may be same or different, and C1-C6 alkoxycarbonyl group, or —A4—R13 (wherein A4 represents C1-C6 alkylene group, halo C1-C6 alkylene group, C3-C6 alkenylene group, halo C3-C6 alkenylene group, C3-C6 alkynylene group or halo C3-C6 alkynylene group, and R13 represents hydrogen atom, halogen atom, C3-C6 cycloalkyl group, halo C3-C6 cycloalkyl group, C1-C6 alkoxycarbonyl group, phenyl group, substituted phenyl group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group, halo C1-C6 alkylsulfonyl group, mono C1-C6 alkylamino group, di C1-C6 alkylamino group in which C1-C6 alkyl groups may be same or different, and C1-C6 alkoxycarbonyl group, or —A5—R14 (wherein A5 represents —O—, —S—, —SO—, —SO2— or —C(═O)—, and R14 represents C1-C6 alkyl group, halo C1-C6 alkyl group, C3-C6 alkenyl group, halo C3-C6 alkenyl group, C3-C6 alkynyl group, halo C3-C6 alkynyl group, C3-C6 cycloalkyl group, halo C3-C6 cycloalkyl group, phenyl group, substituted phenyl group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group, halo C1-C6 alkylsulfonyl group, mono C1-C6 alkylamino group, di C1-C6 alkylamino group in which C1-C6 alkyl groups may be same or different, and C1-C6 alkoxycarbonyl group, heterocyclic group, or substituted heterocyclic group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group, halo C1-C6 alkylsulfonyl group, mono C1-C6 alkylamino group, di C1-C6 alkylamino group in which C1-C6 alkyl groups may be same or different, and C1-C6 alkoxycarbonyl group)), and (2) in cases where A3 represents —C(═O)— or —C(═NOR12)— wherein R12 is as defined above, R11 represents hydrogen atom, C1-C6 alkyl group, halo C1-C6 alkyl group, C2-C6 alkenyl group, halo C2-C6 alkenyl group, C3-C6 cycloalkyl group, halo C3-C6 cycloalkyl group, C1-C6 alkoxy group, C1-C6 alkylthio group, mono C1-C6 alkylamino group, di C1-C6 alkylamino group in which C1-C6 alkyl groups may be same or different, phenyl group, substituted phenyl group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group, halo C1-C6 alkylsulfonyl group, mono C1-C6 alkylamino group, di C1-C6 alkylamino group in which C1-C6 alkyl groups may be same or different, and C1-C6 alkoxycarbonyl group, phenylamino group, substituted phenylamino group having on the ring thereof, at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group, halo C1-C6 alkylsulfonyl group, mono C1-C6 alkylamino group, di C1-C6 alkylamino group in which C1-C6 alkyl groups may be same or different, and C1-C6 alkoxycarbonyl group, heterocyclic group, or substituted heterocyclic group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group, halo C1-C6 alkylsulfonyl group, mono C1-C6 alkylamino group, di C1-C6 alkylamino group in which C1-C6 alkyl groups may be same or different, and C1-C6 alkoxycarbonyl group, and (3) in cases where A3 represents C1-C6 alkylene group, halo C1-C6 alkylene group, C2-C6 alkenylene group, halo C2-C6 alkenylene group, C2-C6 alkynylene group or halo C3-C6 alkynylene group, R11 represents hydrogen atom, hydroxy group, halogen atom, C3-C6 cycloalkyl group, halo C3-C6 cycloalkyl group, C1-C6 alkoxycarbonyl group, phenyl group, substituted phenyl group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group, halo C1-C6 alkylsulfonyl group, mono C1-C6 alkylamino group, di C1-C6 alkylamino group in which C1-C6 alkyl groups may be same or different, and C1-C6 alkoxycarbonyl group, heterocyclic group, substituted heterocyclic group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group, halo C1-C6 alkylsulfonyl group, mono C1-C6 alkylamino group, di C1-C6 alkylamino group in which C1-C6 alkyl groups may be same or different, and C1-C6 alkoxycarbonyl group, or —A6—R15 (wherein A6 represents —O—, —S—, —SO— or —SO2—, and R15 represents C3-C6 cycloalkyl group, halo C3-C6 cycloalkyl group, phenyl group, substituted phenyl group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group, halo C1-C6 alkylsulfonyl group, mono C1-C6 alkylamino group, di C1-C6 alkylamino group in which C1-C6 alkyl groups may be same or different, and C1-C6 alkoxycarbonyl group, heterocyclic group, substituted heterocyclic group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group, halo C1-C6 alkylsulfonyl group, mono C1-C6 alkylamino group, di C1-C6 alkylamino group in which C1-C6 alkyl groups may be same or different, and C1-C6 alkoxycarbonyl group, or —A7—R16 (wherein A7 represents C1-C6 alkylene group, halo C1-C6 alkylene group, C2-C6 alkenylene group, halo C2-C6 alkenylene group, C2-C6 alkynylene group or halo C3-C6 alkynylene group, and R16 represents hydrogen atom, halogen atom, C3-C6 cycloalkyl group, halo C3-C6 cycloalkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group, halo C1-C6 alkylsulfonyl group, phenyl group, substituted phenyl group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group, halo C1-C6 alkylsulfonyl group, mono C1-C6 alkylamino group, di C1-C6 alkylamino group in which C1-C6 alkyl groups may be same or different, and C1-C6 alkoxycarbonyl group, phenoxy group, substituted phenoxy group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group, halo C1-C6 alkylsulfonyl group, mono C1-C6 alkylamino group, di C1-C6 alkylamino group in which C1-C6 alkyl groups may be same or different, and C1-C6 alkoxycarbonyl group, phenylthio group, substituted phenylthio group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group, halo C1-C6 alkylsulfonyl group, mono C1-C6 alkylamino group, di C1-C6 alkylamino group in which C1-C6 alkyl groups may be same or different, and C1-C6 alkoxycarbonyl group, heterocyclic group, or substituted heterocyclic group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group, halo C1-C6 alkylsulfonyl group, mono C1-C6 alkylamino group, di C1-C6 alkylamino group in which C1-C6 alkyl groups may be same or different, and C1-C6 alkoxycarbonyl group))]; and 1 represents an integer of 0 to 4; and alternatively, X may be taken conjointly with the adjacent carbon atom on the phenyl ring to form a fused ring, and said fused ring may have at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group, halo C1-C6 alkylsulfonyl group, mono C1-C6 alkylamino group, di C1-C6 alkylamino group in which C1-C6 alkyl groups may be same or different, and C1-C6 alkoxycarbonyl group; and Y may be same or different and represents halogen atom, cyano group, nitro group, halo C3-C6 cycloalkyl group, tri C1-C6 alkylsilyl group in which C1-C6 alkyl groups may be same or different, phenyl group, substituted phenyl group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group, halo C1-C6 alkylsulfonyl group, mono C1-C6 alkylamino group, di C1-C6 alkylamino group in which C1-C6 alkyl groups may be same or different, and C1-C6 alkoxycarbonyl group, heterocyclic group, substituted heterocyclic group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group, halo C1-C6 alkylsulfonyl group, mono C1-C6 alkylamino group, di C1-C6 alkylamino group in which C1-C6 alkyl groups may be same or different, and C1-C6 alkoxycarbonyl group, or —A3—R11 wherein A3 and R11 are as defined above; and m represents an integer of 0 to 5; and Y may be taken conjointly with an adjacent carbon atom on the phenyl ring to form a fused ring, and said fused ring may have at least one, same or different substituents selected from the group consisting of halogen atom, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group, halo C1-C6 alkylsulfonyl group, phenyl group, substituted phenyl group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group, halo C1-C6 alkylsulfonyl group, mono C1-C6 alkylamino group, di C1-C6 alkylamino group in which C1-C6 alkyl groups may be same or different, and C1-C6 alkoxycarbonyl group, heterocyclic group, and substituted heterocyclic group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group, halo C1-C6 alkylsulfonyl group, mono C1-C6 alkylamino group, di C1-C6 alkylamino group in which C1-C6 alkyl groups may be same or different, and C1-C6 alkoxycarbonyl group; and n represents an integer of 0 to 2; provided that when X, R2 and R3 simultaneously represent hydrogen atom, m represents an integer of 2, Y of the 2-position represents fluorine atom and Y of the 3-position represents chlorine atom, then A1 is not propylene group, R1 is not methyl group and n is not an integer of 0.
  • 2. A phthalamide derivative or salt thereof according to claim 1,wherein A1 represents C1-C8 alkylene group, substituted C1-C8 alkylene group having at least one, same or different substituents selected from the group consisting of halogen atom, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group, halo C1-C6 alkylsulfonyl group, C1-C6 alkylthio C1-C6 alkyl group, phenyl group and substituted phenyl group having at least one, same or different substituents selected from the group consisting of halogen atom, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group and halo C1-C6 alkylsulfonyl group, C3-C8 alkenylene group, substituted C3-C8 alkenylene group having at least one, same or different substituents selected from the group consisting of halogen atom, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group, halo C1-C6 alkylsulfonyl group, and C1-C6 alkylthio C1-C6 alkyl group, C3-C8 alkynylene group, or substituted C3-C8 alkynylene group having at least one, same or different substituents selected from the group consisting of halogen atom, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group, halo C1-C6 alkylsulfonyl group and C1-C6 alkylthio C1-C6 alkyl group, further, an arbitrary saturated carbon atom in said C1-C8 alkylene group, substituted C1-C8 alkylene group, C3-C8 alkenylene group, substituted C3-C8 alkenylene group, C3-C8 alkynylene group and substituted C3-C8 alkynylene group may be substituted with a C2-C5 alkylene group to form a C3-C6 cycloalkane ring, and arbitrary two carbon atoms in said C1-C8 alkylene group, substituted C1-C8 alkylene group, C3-C8 alkenylene group and substituted C3-C8 alkenylene group may be taken conjointly with an alkylene group or an alkenylene group to form a C3-C6 cycloalkane ring or C3-C6 cycloalkene ring; R1 represents hydrogen atom, mercapto group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C3-C6 cycloalkyl group, halo C3-C6 cycloalkyl group, phenyl group, substituted phenyl group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group, halo C1-C6 alkylsulfonyl group, mono C1-C6 alkylamino group, di C1-C6 alkylamino group in which C1-C6 alkyl groups may be same or different, and C1-C6 alkoxycarbonyl group, phenylthio group, substituted phenylthio group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group, halo C1-C6 alkylsulfonyl group, mono C1-C6 alkylamino group, di C1-C6 alkylamino group in which C1-C6 alkyl groups may be same or different, and C1-C6 alkoxycarbonyl group, heterocyclic group, substituted heterocyclic group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group, halo C1-C6 alkylsulfonyl group, mono C1-C6 alkylamino group, di C1-C6 alkylamino group in which C1-C6 alkyl groups may be same or different, and C1-C6 alkoxycarbonyl group, or —A2—R4 [wherein A2 represents —C(═O)—, —C(═S)—, or —C(═NR5)— (in which R5 represents hydrogen atom, C1-C6 alkyl group, C1-C6 alkoxy group, mono C1-C6 alkylamino group, di C1-C6 alkylamino group in which C1-C6 alkyl groups may be same or different, C1-C6 alkoxycarbonyl group, phenyl group or substituted phenyl group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group and halo C1-C6 alkylsulfonyl group), C1-C8 alkylene group, halo C1-C8 alkylene group, C3-C6 alkenylene group, halo C3-C6 alkenylene group, C3-C6 alkynylene group or halo C3-C6 alkynylene group; and (1) in cases where A2 represents —C(═O)—, —C(═S)— or —C(═NR5)— wherein R5 is as defined above, R4 represents hydrogen atom, C1-C6 alkyl group, halo C1-C6 alkyl group, C3-C6 cycloalkyl group, halo C3-C6 cycloalkyl group, phenyl group, substituted phenyl group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group and halo C1-C6 alkylsulfonyl group, heterocyclic group, substituted heterocyclic group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group and halo C1-C6 alkylsulfonyl group, or —Z1—R6 wherein Z1 represents —O—, —S— or —N(R7)— (wherein R7 represents hydrogen atom, C1-C6 alkyl group, C1-C6 alkylcarbonyl group, halo C1-C6 alkylcarbonyl group or C1-C6 alkoxycarbonyl group), and R6 represents hydrogen atom, C1-C6 alkyl group, halo C1-C6 alkyl group, C3-C6 alkenyl group, halo C3-C6 alkenyl group, C3-C6 alkynyl group, halo C3-C6 alkynyl group, C3-C6 cycloalkyl group, phenyl group, substituted phenyl group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group and halo C1-C6 alkylsulfonyl group, phenyl C1-C4 alkyl group, substituted phenyl C1-C4 alkyl group having, on the ring thereof, at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group and halo C1-C6 alkylsulfonyl group, heterocyclic group, or substituted heterocyclic group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group and halo C1-C6 alkylsulfonyl group, and (2) in cases where A2 represents C1-C8 alkylene group, halo C1-C8 alkylene group, C3-C6 alkenylene group, halo C3-C6 alkenylene group, C3-C6 alkynylene group or halo C3-C6 alkynylene group, R4 represents hydrogen atom, halogen atom, cyano group, nitro group, C3-C6 cycloalkyl group, halo C3-C6 cycloalkyl group, C1-C6 alkoxycarbonyl group, mono C1-C6 alkylaminocarbonyl group, di C1-C6 alkylaminocarbonyl group in which C1-C6 alkyl groups may be same or different, phenyl group, substituted phenyl group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group and halo C1-C6 alkylsulfonyl group, heterocyclic group, substituted heterocyclic group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group, and halo C1-C6 alkylsulfonyl group, or —Z2—R8 wherein Z2 represents —O—, —S—, —SO—, —SO2—, —N(R9)— (wherein R9 represents hydrogen atom, C1-C6 alkyl group, C1-C6 alkylcarbonyl group, halo C1-C6 alkylcarbonyl group, C1-C6 alkoxycarbonyl group, phenylcarbonyl group, or substituted phenylcarbonyl group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfonyl group, halo C1-C6 alkylsulfonyl group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group and halo C1-C6 alkylsulfonyl group), —C(═O)— or —C(═NOR10)— (wherein R10 represents hydrogen atom, C1-C6 alkyl group, halo C1-C6 alkyl group, C3-C6 alkenyl group, halo C3-C6 alkenyl group, C3-C6 alkynyl group, halo C3-C6 alkynyl group, C3-C6 cycloalkyl group, phenyl C1-C4 alkyl group or substituted phenyl C1-C4 alkyl group having, on the ring thereof, at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group, and halo C1-C6 alkylsulfonyl group) and R8 represents hydrogen atom, C1-C6 alkyl group, halo C1-C6 alkyl group, C3-C6 alkenyl group, halo C3-C6 alkenyl group, C3-C6 alkynyl group, halo C3-C6 alkynyl group, C3-C6 cycloalkyl group, C1-C6 alkylcarbonyl group, halo C1-C6 alkylcarbonyl group, C1-C6 alkoxycarbonyl group, mono C1-C6 alkylaminocarbonyl group, di C1-C6 alkylaminocarbonyl group in which C1-C6 alkyl groups may be same or different, phenyl group, substituted phenyl group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group and halo C1-C6 alkylsulfonyl group, phenyl C1-C4 alkyl group, substituted phenyl C1-C4 alkyl group having, on the ring thereof, at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group and halo C1-C6 alkylsulfonyl group, heterocyclic group, or substituted heterocyclic group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group and halo C1-C6 alkylsulfonyl group], or alternatively, R1 may be combined with A1 to form a 5- to 8-membered ring which may be intercepted by 1 or 2, same or different oxygen atoms, sulfur atoms or nitrogen atoms; R2 and R3 which may be same or different, represent hydrogen atom, C1-C6 cycloalkyl group or —A2—R4 wherein A2and R4 are as defined above; or alternatively, R2 may be combined with A1 or R1 to form a 5- to 7-membered ring which may be intercepted by 1 or 2, same or different oxygen atoms, sulfur atoms or nitrogen atoms; X which may be same or different, represents halogen atom, cyano group, nitro group, C1-C6 alkyl group, halo C1-C6 alkyl group, C2-C6 alkenyl group, halo C1-C6 alkenyl group, C2-C6 alkynyl group, halo C2-C6 alkynyl group, C3-C6 cycloalkyl group, halo C3-C6 cycloalkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group, halo C1-C6 alkylsulfonyl group, or C1-C6 alkoxycarbonyl group and 1 represents an integer of 0 to 4; and alternatively, X may be taken conjointly with the adjacent carbon atom on the phenyl ring to form a fused ring, and said fused ring may have at least one, same or different substituents selected from the group consisting of halogen atom, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group and halo C1-C6 alkylsulfonyl group; and Y may be same or different and represents halogen atom, cyano group, nitro group, halo C3-C6 cycloalkyl group, tri C1-C6 alkylsilyl group in which C1-C6 alkyl groups may be same or different, phenyl group, substituted phenyl group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group and halo C1-C6 alkylsulfonyl group, heterocyclic group, substituted heterocyclic group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group and halo C1-C6 alkylsulfonyl group, or —A3—R11 [wherein A3 represents —O—, —S—, —SO—, —SO2—, —C(═O)—, —C(═NOR12)— (in which R12 represents hydrogen atom, C1-C6 alkyl group, halo C1-C6 alkyl group, C3-C6 alkenyl group, halo C3-C6 alkenyl group, C3-C6 alkynyl group, C3-C6 cycloalkyl group, phenyl C1-C4 alkyl group or substituted phenyl C1-C4 alkyl group having, on the ring thereof, at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group, and halo C1-C6 alkylsulfonyl group), C1-C6 alkylene group, halo C1-C6 alkylene group, C2-C6 alkenylene group, halo C2-C6 alkenylene group, C2-C6 alkynylene group or halo C3-C6 alkynylene group; and (1) in cases where A3 represents —O—, —S—, —SO— or —SO2—, R11 represents phenyl group, substituted phenyl group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group, and halo C1-C6 alkylsulfonyl group, heterocyclic group, substituted heterocyclic group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group and halo C1-C6 alkylsulfonyl group, or —A4—R13 (wherein A4 represents C1-C6 alkylene group, halo C1-C6 alkylene group, C3-C6 alkenylene group, halo C3-C6 alkenylene group, C3-C6 alkynylene group or halo C3-C6 alkynylene group, and R13 represents hydrogen atom, halogen atom, C3-C6 cycloalkyl group, halo C3-C6 cycloalkyl group, phenyl group, substituted phenyl group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group, and halo C1-C6 alkylsulfonyl group, or —A5—R14 (wherein A5 represents —O—, —S—, —SO—, —SO2— or —C(═O)—, and R14 represents C1-C6 alkyl group, halo C1-C6 alkyl group, C3-C6 alkenyl group, halo C3-C6 alkenyl group, C3-C6 alkynyl group, halo C3-C6 alkynyl group, C3-C6 cycloalkyl group, halo C3-C6 cycloalkyl group, phenyl group, substituted phenyl group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group and halo C1-C6 alkylsulfonyl group, heterocyclic group, or substituted heterocyclic group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group and halo C1-C6 alkylsulfonyl group)), and (2) in cases where A3 represents —C(═O)— or —C(═NOR12)— wherein R12 is as defined above, R11 represents hydrogen atom, C1-C6 alkyl group, halo C1-C6 alkyl group, C2-C6 alkenyl group, halo C2-C6 alkenyl group, C3-C6 cycloalkyl group, halo C3-C6 cycloalkyl group, C1-C6 alkoxy group, C1-C6 alkylthio group, mono C1-C6 alkylamino group, di C1-C6 alkylamino group in which C1-C6 alkyl groups may be same or different, phenyl group, substituted phenyl group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group and halo C1-C6 alkylsulfonyl group, phenylamino group, substituted phenylamino group having on the ring thereof, at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group and halo C1-C6 alkylsulfonyl group, heterocyclic group, or substituted heterocyclic group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group and halo C1-C6 alkylsulfonyl group, and (3) in cases where A3 represents C1-C6 alkylene group, halo C1-C6 alkylene group, C2-C6 alkenylene group, halo C2-C6 alkenylene group, C2-C6 alkynylene group or halo C3-C6 alkynylene group, R11 represents hydrogen atom, hydroxy group, halogen atom, C3-C6 cycloalkyl group, halo C3-C6 cycloalkyl group, C1-C6 alkoxycarbonyl group, phenyl group, substituted phenyl group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group and halo C1-C6 alkylsulfonyl group, heterocyclic group, substituted heterocyclic group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group and halo C1-C6 alkylsulfonyl group, or —A6—R15 (wherein A6 represents —O—, —S—, —SO— or —SO2—, and R15 represents C3-C6 cycloalkyl group, halo C3-C6 cycloalkyl group, phenyl group, substituted phenyl group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group and halo C1-C6 alkylsulfonyl group, heterocyclic group, substituted heterocyclic group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group and halo C1-C6 alkylsulfonyl group, or —A7—R16 (wherein A7 represents C1-C6 alkylene group, halo C1-C6 alkylene group, C2-C6 alkenylene group, halo C2-C6 alkenylene group, C2-C6 alkynylene group or halo C3-C6 alkynylene group, and R16 represents hydrogen atom, halogen atom, C3-C6 cycloalkyl group, halo C3-C6 cycloalkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group, halo C1-C6 alkylsulfonyl group, phenyl group, substituted phenyl group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group and halo C1-C6 alkylsulfonyl group, phenoxy group, substituted phenoxy group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group and halo C1-C6 alkylsulfonyl group, phenylthio group, substituted phenylthio group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group and halo C1-C6 alkylsulfonyl group, heterocyclic group, or substituted heterocyclic group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group and halo C1-C6 alkylsulfonyl group))] and m represents an integer of 1 to 5; and Y may be taken conjointly with an adjacent carbon atom on the phenyl ring to form a fused ring, and said fused ring may have at least one, same or different substituents selected from the group consisting of halogen atom, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group and halo C1-C6 alkylsulfonyl group; and n represents an integer of 0 to 2.
  • 3. A phthalamide derivative or salt thereof according to claim 2,wherein A1 represents C1-C8 alkylene group, substituted C1-C8 alkylene group having at least one, same or different substituents selected from the group consisting of halogen atom, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group, halo C1-C6 alkylsulfonyl group and C1-C6 alkylthio C1-C6 alkyl group and further, an arbitrary saturated carbon atom in said C1-C8 alkylene group and substituted C1-C8 alkylene group may be substituted with a C2-C5 alkylene group to form a C3-C6 cycloalkane ring, and arbitrary two carbon atoms in said C1-C8 alkylene group and substituted C1-C8 alkylene group may be taken conjointly with an alkylene group or an alkenylene group to form a C3-C6 cycloalkane ring; R1 represents hydrogen atom, mercapto group, C1-C6 alkyl group, halo C1-C6 alkyl group, C3-C6 alkenyl group, halo C3-C6 alkenyl group, C3-C6 alkynyl group, halo C3-C6 alkynyl group, C3-C6 cycloalkyl group, halo C3-C6 cycloalkyl group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkoxy C1-C6 alkyl group, C1-C6 alkylthio C1-C6 alkyl group, mono C1-C6 alkylamino C1-C6 alkyl group, di C1-C6 alkylamino C1-C6 alkyl group in which C1-C6 alkyl groups may be same or different, C1-C6 alkylcarbonyl group, halo C1-C6 alkylcarbonyl group, C1-C6 alkylthiocarbonyl group, C1-C6 alkoxycarbonyl group, mono C1-C6 alkylaminocarbonyl group, di C1-C6 alkylaminocarbonyl group in which C1-C6 alkyl groups may be same or different, mono C1-C6 alkylamino thiocarbonyl group, di C1-C6 alkylamino thiocarbonyl group in which C1-C6 alkyl groups may be same or different, C1-C6 alkylcarbonyl C1-C6 alkyl group, C1-C6 alkoxyimino C1-C6 alkyl group, C1-C6 alkoxycarbonyl C1-C6 alkyl group, mono C1-C6 alkylaminocarbonyl C1-C6 alkyl group, di C1-C6 alkylaminocarbonyl C1-C6 alkyl group in which C1-C6 alkyl groups may be same or different, phenyl group, substituted phenyl group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group, halo C1-C6 alkylsulfonyl group, mono C1-C6 alkylamino group, di C1-C6 alkylamino group in which C1-C6 alkyl groups may be same or different and C1-C6 alkoxycarbonyl group, phenyl C1-C6 alkyl group, substituted phenyl C1-C6 alkyl group having, on the ring thereof, at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group, halo C1-C6 alkylsulfonyl group, mono C1-C6 alkylamino group, di C1-C6 alkylamino group in which C1-C6 alkyl groups may be same or different, and C1-C6 alkoxycarbonyl group, phenylcarbonyl group, substituted phenylcarbonyl group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group, halo C1-C6 alkylsulfonyl group, mono C1-C6 alkylamino group, di C1-C6 alkylamino group in which C1-C6 alkyl groups may be same or different and C1-C6 alkoxycarbonyl group, phenylthio group, substituted phenylthio group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group, halo C1-C6 alkylsulfonyl group, mono C1-C6 alkylamino group, di C1-C6 alkylamino group in which C1-C6 alkyl groups may be same or different and C1-C6 alkoxycarbonyl group, heterocyclic group, or substituted heterocyclic group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group, halo C1-C6 alkylsulfonyl group, mono C1-C6 alkylamino group, di C1-C6 alkylamino group in which C1-C6 alkyl groups may be same or different and C1-C6 alkoxycarbonyl group, or alternatively, R1 may be combined with A1 to form a 5- to 8-membered ring which may be intercepted by 1 or 2, same or different oxygen atoms, sulfur atoms or nitrogen atoms; R2 and R3 which may be same or different, represent hydrogen atom, C1-C6 alkyl group; or alternatively, R2 may be combined with A1 or R1 to form a 5- to 7-membered ring which may be intercepted by 1 or 2, same or different oxygen atoms, sulfur atoms or nitrogen atoms; X which may be same or different, represents halogen atom, nitro group, C1-C6 alkyl group, halo C1-C6 alkyl group, C2-C6 alkenyl group, halo C2-C6 alkenyl group, C2-C6 alkynyl group, halo C2-C6 alkynyl group, C3-C6 cycloalkyl group, halo C3-C6 cycloalkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group or halo C1-C6 alkylsulfonyl group and l represents an integer of 0 to 4; and alternatively, X may be taken conjointly with the adjacent carbon atom on the phenyl ring to form a fused ring, and said fused ring may have at least one, same or different substituents selected from the group consisting of halogen atom, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group and halo C1-C6 alkylsulfonyl group; and Y may be same or different and represents halogen atom, C1-C6 alkyl group, halo C1-C6 alkyl group, hydroxy halo C1-C6 alkyl group, C1-C6 alkoxy halo C1-C6 alkyl group, C1-C6 alkylthio halo C1-C6 alkyl group, C3-C6 alkenyl group, halo C3-C6 alkenyl group, C3-C6 alkynyl group, halo C3-C6 alkynyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkoxy halo C1-C6 alkoxy group, C1-C6 alkylthio halo C1-C6 alkoxy group, halo C1-C6 alkoxy halo C1-C6 alkoxy group, halo C3-C6 alkenyloxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, halo C1-C6 alkoxy halo C1-C6 alkylthio group, halo C1-C6 alkenylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group, halo C1-C6 alkylsulfonyl group, mono C1-C6 alkylamino group, di C1-C6 alkylamino group in which C1-C6 alkyl groups may be same or different, C1-C6 alkoxycarbonyl group, C3-C6 cycloalkyl group, halo C3-C6 cycloalkyl group, phenyl group, substituted phenyl group having at least one, same or different substituents selected from the group consisting of halogen atom, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, halo C1-C6 alkylsulfinyl group, and halo C1-C6 alkylsulfonyl group, phenoxy group, substituted phenoxy group having at least one, same or different substituents selected from the group consisting of halogen atom, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, halo C1-C6 alkylsulfinyl group, and halo C1-C6 alkylsulfonyl group, phenylthio group, substituted phenylthio group having at least one, same or different substituents selected from the group consisting of halogen atom, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, halo C1-C6 alkylsulfinyl group and halo C1-C6 alkylsulfonyl group, pyridyloxy group, substituted pyridyloxy group having at least one, same or different substituents selected from the group consisting of halogen atom, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, halo C1-C6 alkylsulfinyl group and halo C1-C6 alkylsulfonyl group, pyridylthio group, substituted pyridylthio group having at least one, same or different substituents selected from the group consisting of halogen atom, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, halo C1-C6 alkylsulfinyl group and halo C1-C6 alkylsulfonyl group; and m represents an integer of 1 to 5; and Y may be taken conjointly with an adjacent carbon atom on the phenyl ring to form a fused ring, and said fused ring may have at least one, same or different substituents selected from the group consisting of halogen atom, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group and halo C1-C6 alkylsulfonyl group; and n represents an integer of 0 to 2.
  • 4. A phthalamide derivative or salt thereof according to claim 3, wherein A1 represents C1-C8 alkylene group;R1 represents hydrogen atom, C1-C6 alkyl group, halo C1-C6 alkyl group, C3-C6 alkenyl group, C3-C6 alkynyl group, C3-C6 cycloalkyl group, C1-C6 alkylthio group, C1-C6 alkoxy C1-C6 alkyl group, C1-C6 alkylthio C1-C6 alkyl group, C1-C6 alkylcarbonyl group, mono C1-C6 alkylaminocarbonyl group, di C1-C6 alkylaminocarbonyl group in which C1-C6 alkyl groups may be same or different, mono C1-C6 alkylaminothiocarbonyl group, di C1-C6 alkylaminothiocarbonyl group in which C1-C6 alkyl groups may be same or different, C1-C6 alkylcarbonyl C1-C6 alkyl group, C1-C6 alkoxyimino C1-C6 alkyl group, C1-C6 alkoxycarbonyl C1-C6 alkyl group, mono C1-C6 alkylaminocarbonyl C1-C6 alkyl group or di C1-C6 alkylaminocarbonyl C1-C6 alkyl group in which C1-C6 alkyl groups may be same or different; R2 and R3 which may be same or different, represent hydrogen atom or C1-C6 alkyl group; X which may be same or different, represents halogen atom, nitro group, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group or halo C1-C6 alkylsulfonyl group; and l represents an integer of 0 to 4; and alternatively, X may be taken conjointly with the adjacent carbon atom on the phenyl ring to form a fused ring, and said fused ring may have at least one, same or different substituents selected from the group consisting of halogen atom, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group and halo C1-C6 alkylsulfonyl group; Y may be same or different and represents halogen atom, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, halo C1-C6 alkoxy halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group, halo C1-C6 alkylsulfonyl group, substituted phenyl group having at least one, same or different substituents selected from the group consisting of halogen atom, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, halo C1-C6 alkylsulfinyl group and halo C1-C6 alkylsulfonyl group, substituted phenoxy group having at least one, same or different substituents selected from the group consisting of halogen atom, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, halo C1-C6 alkylsulfinyl group and halo C1-C6 alkylsulfonyl group, or substituted pyridyloxy group having at least one, same or different substituents selected from the group consisting of halogen atom, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, halo C1-C6 alkylsulfinyl group and halo C1-C6 alkylsulfonyl group; and m represents an integer of 1 to 5; and Y may be taken conjointly with an adjacent carbon atom on the phenyl ring to form a fused ring, and said fused ring may have at least one, same or different substituents selected from the group consisting of halogen atom, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, halo C1-C6 alkylsulfinyl group and halo C1-C6 alkylsulfonyl group; and n represents an integer of 0 to 2.
  • 5. An agrohorticultural insecticide characterized by containing, as an active ingredient thereof, a phthalamide derivative represented by the following general formula (I) or salt thereof: wherein A1 represents C1-C8 alkylene group, substituted C1-C8 alkylene group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group, halo C1-C6 alkylsulfonyl group, hydroxy C1-C6 alkyl group, C1-C6 alkoxy C1-C6 alkyl group, C1-C6 alkylthio C1-C6 alkyl group, C1-C6 alkoxycarbonyl group, phenyl group and substituted phenyl group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C1-C6, alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group, halo C1-C6 alkylsulfonyl group, mono C1-C6 alkylamino group, di C1-C6 alkylamino group in which C1-C6 alkyl groups may be same or different, and C1-C6 alkoxycarbonyl group, C3-C8 alkenylene group, substituted C3-C8 alkenylene group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group, halo C1-C6 alkylsulfonyl group, C1-C6 alkylthio C1-C6 alkyl group, C1-C6 alkoxycarbonyl group, phenyl group and substituted phenyl group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group, halo C1-C6 alkylsulfonyl group, mono C1-C6 alkylamino group, di C1-C6 alkylamino group in which C1-C6 alkyl groups may be same or different, and C1-C6 alkoxycarbonyl group, C3-C8 alkynylene group, or substituted C3-C8 alkynylene group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group, halo C1-C6 alkylsulfonyl group, C1-C6 alkylthio C1-C6 alkyl group, C1-C6 alkoxycarbonyl group, phenyl group and substituted phenyl group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group, halo C1-C6 alkylsulfonyl group, mono C1-C6 alkylamino group, di C1-C6 alkylamino group in which C1-C6 alkyl groups may be same or different, and C1-C6 alkoxycarbonyl group,further, an arbitrary saturated carbon atom in said C1-C8 alkylene group, substituted C1-C8 alkylene group, C3-C8 alkenylene group, substituted C3-C8 alkenylene group, C3-C8 alkynylene group and substituted C3-C8 alkynylene group may be substituted with a C2-C5 alkylene group to form a C3-C6 cycloalkane ring, and arbitrary two carbon atoms in said C1-C8 alkylene group, substituted C1-C8 alkylene group, C3-C8 alkenylene group and substituted C3-C8 alkenylene group may be taken conjointly with an alkylene group or an alkenylene group to form a C3-C6 cycloalkane ring or C3-C6 cycloalkene ring; R1 represents hydrogen atom, mercapto group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C3-C6 cycloalkyl group, halo C3-C6 cycloalkyl group, phenyl group, substituted phenyl group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group, halo C1-C6 alkylsulfonyl group, mono C1-C6 alkylamino group, di C1-C6 alkylamino group in which C1-C6 alkyl groups may be same or different, and C1-C6 alkoxycarbonyl group, phenylthio group, substituted phenylthio group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group, halo C1-C6 alkylsulfonyl group, mono C1-C6 alkylamino group, di C1-C6 alkylamino group in which C1-C6 alkyl groups may be same or different, and C1-C6 alkoxycarbonyl group, heterocyclic group, substituted heterocyclic group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group, halo C1-C6 alkylsulfonyl group, mono C1-C6 alkylamino group, di C1-C6 alkylamino group in which C1-C6 alkyl groups may be same or different, and C1-C6 alkoxycarbonyl group, or —A2—R4 [wherein A2 represents —C(═O)—, —C(═S)—, or —C(═NR5)— (in which R5 represents hydrogen atom, C1-C6 alkyl group, C1-C6 alkoxy group, mono C1-C6 alkylamino group, di C1-C6 alkylamino group in which C1-C6 alkyl groups may be same or different, C1-C6 alkoxycarbonyl group, phenyl group or substituted phenyl group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group, halo C1-C6 alkylsulfonyl group, mono C1-C6 alkylamino group, di C1-C6 alkylamino group in which C1-C6 alkyl groups may be same or different, and C1-C6 alkoxycarbonyl group), C1-C8 alkylene group, halo C1-C8 alkylene group, C3-C6 alkenylene group, halo C3-C6 alkenylene group, C3-C6 alkynylene group or halo C3-C6 alkynylene group; and (1) in cases where A2 represents —C(═O)—, —C(═S)— or —C(═NR5)— wherein R5 is as defined above, R4 represents hydrogen atom, C1-C6 alkyl group, halo C1-C6 alkyl group, C3-C6 cycloalkyl group, halo C3-C6 cycloalkyl group, phenyl group, substituted phenyl group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group, halo C1-C6 alkylsulfonyl group, mono C1-C6 alkylamino group, di C1-C6 alkylamino group in which C1-C6 alkyl groups may be same or different, and C1-C6 alkoxycarbonyl group, heterocyclic group, substituted heterocyclic group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group, halo C1-C6 alkylsulfonyl group, mono C1-C6 alkylamino group, di C1-C6 alkylamino group in which C1-C6 alkyl groups may be same or different, and C1-C6 alkoxycarbonyl group, or —Z1—R6 wherein Z1 represents —O—, —S— or —N(R7)— (wherein R7 represents hydrogen atom, C1-C6 alkyl group, C1-C6 alkylcarbonyl group, halo C1-C6 alkylcarbonyl group or C1-C6 alkoxycarbonyl group), and R6 represents hydrogen atom, C1-C6 alkyl group, halo C1-C6 alkyl group, C3-C6 alkenyl group, halo C3-C6 alkenyl group, C3-C6 alkynyl group, halo C3-C6 alkynyl group, C3-C6 cycloalkyl group, phenyl group, substituted phenyl group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group, halo C1-C6 alkylsulfonyl group, mono C1-C6 alkylamino group, di C1-C6 alkylamino group in which C1-C6 alkyl groups may be same or different, and C1-C6 alkoxycarbonyl group, phenyl C1-C4 alkyl group, substituted phenyl C1-C4 alkyl group having, on the ring thereof, at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group, halo C1-C6 alkylsulfonyl group, mono C1-C6 alkylamino group, di C1-C6 alkylamino group in which C1-C6 alkyl groups may be same or different, and C1-C6 alkoxycarbonyl group, heterocyclic group, or substituted heterocyclic group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group, halo C1-C6 alkylsulfonyl group, mono C1-C6 alkylamino group, di C1-C6 alkylamino group in which C1-C6 alkyl groups may be same or different, and C1-C6 alkoxycarbonyl group, and (2) in cases where A2 represents C1-C8 alkylene group, halo C1-C8 alkylene group, C3-C6 alkenylene group, halo C3-C6 alkenylene group, C3-C6 alkynylene group or halo C3-C6 alkynylene group, R4 represents hydrogen atom, halogen atom, cyano group, nitro group, C3-C6 cycloalkyl group, halo C3-C6 cycloalkyl group, C1-C6 alkoxycarbonyl group, mono C1-C6 alkylaminocarbonyl group, di C1-C6 alkylaminocarbonyl group in which C1-C6 alkyl groups may be same or different, phenyl group, substituted phenyl group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group, halo C1-C6 alkylsulfonyl group, mono C1-C6 alkylamino group, di C1-C6 alkylamino group in which C1-C6 alkyl groups may be same or different, and C1-C6 alkoxycarbonyl group, heterocyclic group, substituted heterocyclic group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group, halo C1-C6 alkylsulfonyl group, mono C1-C6 alkylamino group, di C1-C6 alkylamino group in which C1-C6 alkyl groups may be same or different, and C1-C6 alkoxycarbonyl group, or —Z2—R8 wherein Z2 represents —O—, —S—, —SO—, —SO2—, —N(R9)— (wherein R9 represents hydrogen atom, C1-C6 alkyl group, C1-C6 alkylcarbonyl group, halo C1-C6 alkylcarbonyl group, C1-C6 alkoxycarbonyl group, phenylcarbonyl group, or substituted phenylcarbonyl group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group and halo C1-C6 alkylsulfonyl group), —C(═O)— or —C(═NOR10)— (wherein R10 represents hydrogen atom, C1-C6 alkyl group, halo C1-C6 alkyl group, C3-C6 alkenyl group, halo C3-C6 alkenyl group, C3-C6 alkynyl group, halo C3-C6 alkynyl group, C3-C6 cycloalkyl group, phenyl C1-C4 alkyl group or substituted phenyl C1-C4 alkyl group having, on the ring thereof, at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group, halo C1-C6 alkylsulfonyl group, mono C1-C6 alkylamino group, di C1-C6 alkylamino group in which C1-C6 alkyl groups may be same or different, and C1-C6 alkoxycarbonyl group) and R8 represents hydrogen atom, C1-C6 alkyl group, halo C1-C6 alkyl group, C3-C6 alkenyl group, halo C3-C6 alkenyl group, C3-C6 alkynyl group, halo C3-C6 alkynyl group, C3-C6 cycloalkyl group, C1-C6 alkylcarbonyl group, halo C1-C6 alkylcarbonyl group, C1-C6 alkoxycarbonyl group, mono C1-C6 alkylaminocarbonyl group, di C1-C6 alkylaminocarbonyl group in which C1-C6 alkyl groups may be same or different, phenyl group, substituted phenyl group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group, halo C1-C6 alkylsulfonyl group, mono C1-C6 alkylamino group, di C1-C6 alkylamino group in which C1-C6 alkyl groups may be same or different, and C1-C6 alkoxycarbonyl group, phenyl C1-C4 alkyl group, substituted phenyl C1-C4 alkyl group having, on the ring thereof, at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group, halo C1-C6 alkylsulfonyl group, mono C1-C6 alkylamino group, di C1-C6 alkylamino group in which C1-C6 alkyl groups may be same or different, and C1-C6 alkoxycarbonyl group, heterocyclic group, or substituted heterocyclic group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group, halo C1-C6 alkylsulfonyl group, mono C1-C6 alkylamino group, di C1-C6 alkylamino group in which C1-C6 alkyl groups may be same or different, and C1-C6 alkoxycarbonyl group], or alternatively, R1 may be combined with A1 to form a 5- to 8-membered ring which may be intercepted by 1 or 2, same or different oxygen atoms, sulfur atoms or nitrogen atoms; R2 and R3 which may be same or different, represent hydrogen atom, C3-C6 cycloalkyl group or —A2—R4 wherein A2 and R4 are as defined above; or alternatively, R2 may be combined with A1 or R1 to form a 5- to 7-membered ring which may be intercepted by 1 or 2, same or different oxygen atoms, sulfur atoms or nitrogen atoms; X which may be same or different, represents halogen atom, cyano group, nitro group, C3-C6 cycloalkyl group, halo C3-C6 cycloalkyl group, C1-C6 alkoxycarbonyl group, phenyl group, substituted phenyl group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group, halo C1-C6 alkylsulfonyl group, mono C1-C6 alkylamino group, di C1-C6 alkylamino group in which C1-C6 alkyl groups may be same or different, and C1-C6 alkoxycarbonyl group, heterocyclic group, substituted heterocyclic group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group, halo C1-C6 alkylsulfonyl group, mono C1-C6 alkylamino group, di C1-C6 alkylamino group in which C1-C6 alkyl groups may be same or different, and C1-C6 alkoxycarbonyl group, or —A3—R11 [wherein A3 represents —O—, —S—, —SO—, —SO2—, —C(═O)—, —C(═NOR12)— (in which R12 represents hydrogen atom, C1-C6 alkyl group, halo C1-C6 alkyl group, C3-C6 alkenyl group, halo C3-C6 alkenyl group, C3-C6 alkynyl group, C3-C6 cycloalkyl group, phenyl C1-C4 alkyl group or substituted phenyl C1-C4 alkyl group having, on the ring thereof, at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group, halo C1-C6 alkylsulfonyl group, mono C1-C6 alkylamino group, di C1-C6 alkylamino group in which C1-C6 alkyl groups may be same or different, and C1-C6 alkoxycarbonyl group), C1-C6 alkylene group, halo C1-C6 alkylene group, C2-C6 alkenylene group, halo C2-C6 alkenylene group, C2-C6 alkynylene group or, halo C3-C6 alkynylene group; and (1) in cases where A3 represents —O—, —S—, —SO— or —SO2—, R11 represents halo C3-C6 cycloalkyl group, halo C3-C6 cycloalkenyl group, phenyl group, substituted phenyl group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group, halo C1-C6 alkylsulfonyl group, mono C1-C6 alkylamino group, di C1-C6 alkylamino group in which C1-C6 alkyl groups may be same or different, and C1-C6 alkoxycarbonyl group, heterocyclic group, substituted heterocyclic group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group, halo C1-C6 alkylsulfonyl group, mono C1-C6 alkylamino group, di C1-C6 alkylamino group in which C1-C6 alkyl groups may be same or different, and C1-C6 alkoxycarbonyl group, or —A4—R13 (wherein A4 represents C1-C6 alkylene group, halo C1-C6 alkylene group, C3-C6 alkenylene group, halo C3-C6 alkenylene group, C3-C6 alkynylene group or halo C3-C6 alkynylene group, and R13 represents hydrogen atom, halogen atom, C3-C6 cycloalkyl group, halo C3-C6 cycloalkyl group, C1-C6 alkoxycarbonyl group, phenyl group, substituted phenyl group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group, halo C1-C6 alkylsulfonyl group, mono C1-C6 alkylamino group, di C1-C6 alkylamino group in which C1-C6 alkyl groups may be same or different, and C1-C6 alkoxycarbonyl group, or —A5—R14 (wherein A5 represents —O—, —S—, —SO—, —SO2— or —C(═O)—, and R14 represents C1-C6 alkyl group, halo C1-C6 alkyl group, C3-C6 alkenyl group, halo C3-C6 alkenyl group, C3-C6 alkynyl group, halo C3-C6 alkynyl group, C3-C6 cycloalkyl group, halo C3-C6 cycloalkyl group, phenyl group, substituted phenyl group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group, halo C1-C6 alkylsulfonyl group, mono C1-C6 alkylamino group, di C1-C6 alkylamino group in which C1-C6 alkyl groups may be same or different, and C1-C6 alkoxycarbonyl group, heterocyclic group, or substituted heterocyclic group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group, halo C1-C6 alkylsulfonyl group, mono C1-C6 alkylamino group, di C1-C6 alkylamino group in which C1-C6 alkyl groups may be same or different, and C1-C6 alkoxycarbonyl group)), and (2) in cases where A3 represents —C(═O)— or —C(═NOR12)— wherein R12 is as defined above, R11 represents hydrogen atom, C1-C6 alkyl group, halo C1-C6 alkyl group, C2-C6 alkenyl group, halo C2-C6 alkenyl group, C3-C6 cycloalkyl group, halo C3-C6 cycloalkyl group, C1-C6 alkoxy group, C1-C6 alkylthio group, mono C1-C6 alkylamino group, di C1-C6 alkylamino group in which C1-C6 alkyl groups may be same or different, phenyl group, substituted phenyl group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group, halo C1-C6 alkylsulfonyl group, mono C1-C6 alkylamino group, di C1-C6 alkylamino group in which C1-C6 alkyl groups may be same or different, and C1-C6 alkoxycarbonyl group, phenylamino group, substituted phenylamino group having on the ring thereof, at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group, halo C1-C6 alkylsulfonyl group, mono C1-C6 alkylamino group, di C1-C6 alkylamino group in which C1-C6 alkyl groups may be same or different, and C1-C6 alkoxycarbonyl group, heterocyclic group, or substituted heterocyclic group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group, halo C1-C6 alkylsulfonyl group, mono C1-C6 alkylamino group, di C1-C6 alkylamino group in which C1-C6 alkyl groups may be same or different, and C1-C6 alkoxycarbonyl group, and (3) in cases where A3 represents C1-C6 alkylene group, halo C1-C6 alkylene group, C2-C6 alkenylene group, halo C2-C6 alkenylene group, C2-C6 alkynylene group or halo C3-C6 alkynylene group, R11 represents hydrogen atom, hydroxy group, halogen atom, C3-C6 cycloalkyl group, halo C3-C6 cycloalkyl group, C1-C6 alkoxycarbonyl group, phenyl group, substituted phenyl group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group, halo C1-C6 alkylsulfonyl group, mono C1-C6 alkylamino group, di C1-C6 alkylamino group in which C1-C6 alkyl groups may be same or different, and C1-C6 alkoxycarbonyl group, heterocyclic group, substituted heterocyclic group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group, halo C1-C6 alkylsulfonyl group, mono C1-C6 alkylamino group, di C1-C6 alkylamino group in which C1-C6 alkyl groups may be same or different, and C1-C6 alkoxycarbonyl group, or —A6—R15 (wherein A6 represents —O—, —S—, —SO— or —SO2—, and R15 represents C3-C6 cycloalkyl group, halo C3-C6 cycloalkyl group, phenyl group, substituted phenyl group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group, halo C1-C6 alkylsulfonyl group, mono C1-C6 alkylamino group, di C1-C6 alkylamino group in which C1-C6 alkyl groups may be same or different, and C1-C6 alkoxycarbonyl group, heterocyclic group, substituted heterocyclic group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group, halo C1-C6 alkylsulfonyl group, mono C1-C6 alkylamino group, di C1-C6 alkylamino group in which C1-C6 alkyl groups may be same or different, and C1-C6 alkoxycarbonyl group, or —A7—R16 (wherein A7 represents C1-C6 alkylene group, halo C1-C6 alkylene group, C2-C6 alkenylene group, halo C2-C6 alkenylene group, C2-C6 alkynylene group or halo C3-C6 alkynylene group, and R16 represents hydrogen atom, halogen atom, C3-C6 cycloalkyl group, halo C3-C6 cycloalkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group, halo C1-C6 alkylsulfonyl group, phenyl group, substituted phenyl group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group, halo C1-C6 alkylsulfonyl group, mono C1-C6 alkylamino group, di C1-C6 alkylamino group in which C1-C6 alkyl groups may be same or different, and C1-C6 alkoxycarbonyl group, phenoxy group, substituted phenoxy group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group, halo C1-C6 alkylsulfonyl group, mono C1-C6 alkylamino group, di C1-C6 alkylamino group in which C1-C6 alkyl groups may be same or different, and C1-C6 alkoxycarbonyl group, phenylthio group, substituted phenylthio group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group, halo C1-C6 alkylsulfonyl group, mono C1-C6 alkylamino group, di C1-C6 alkylamino group in which C1-C6 alkyl groups may be same or different, and C1-C6 alkoxycarbonyl group, heterocyclic group, or substituted heterocyclic group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group, halo C1-C6 alkylsulfonyl group, mono C1-C6 alkylamino group, di C1-C6 alkylamino group in which C1-C6 alkyl groups may be same or different, and C1-C6 alkoxycarbonyl group))]; and l represents an integer of 0 to 4; and alternatively, X may be taken conjointly with the adjacent carbon atom on the phenyl ring to form a fused ring, and said fused ring may have at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group, halo C1-C6 alkylsulfonyl group, mono C1-C6 alkylamino group, di C1-C6 alkylamino group in which C1-C6 alkyl groups may be same or different, and C1-C6 alkoxycarbonyl group; and Y may be same or different and represents halogen atom, cyano group, nitro group, halo C3-C6 cycloalkyl group, tri C1-C6 alkylsilyl group in which C1-C6 alkyl groups may be same or different, phenyl group, substituted phenyl group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group, halo C1-C6 alkylsulfonyl group, mono C1-C6 alkylamino group, di C1-C6 alkylamino group in which C1-C6 alkyl groups may be same or different, and C1-C6 alkoxycarbonyl group, heterocyclic group, substituted heterocyclic group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group, halo C1-C6 alkylsulfonyl group, mono C1-C6 alkylamino group, di C1-C6 alkylamino group in which C1-C6 alkyl groups may be same or different, and C1-C6 alkoxycarbonyl group, or —A3—R11 wherein A3 and R11 are as defined above; and m represents an integer of 0 to 5; and Y may be taken conjointly with an adjacent carbon atom on the phenyl ring to form a fused ring, and said fused ring may have at least one, same or different substituents selected from the group consisting of halogen atom, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group, halo C1-C6 alkylsulfonyl group, phenyl group, substituted phenyl group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group, halo C1-C6 alkylsulfonyl group, mono C1-C6 alkylamino group, di C1-C6 alkylamino group in which C1-C6 alkyl groups may be same or different, and C1-C6 alkoxycarbonyl group, heterocyclic group, and substituted heterocyclic group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group, halo C1-C6 alkylsulfonyl group, mono C1-C6 alkylamino group, di C1-C6 alkylamino group in which C1-C6 alkyl groups may be same or different, and C1-C6 alkoxycarbonyl group; and n represents an integer of 0 to 2.
  • 6. An agrohorticultural insecticide according to claim 5,wherein A1 represents C1-C8 alkylene group, substituted C1-C8 alkylene group having at least one, same or different substituents selected from the group consisting of halogen atom, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group, halo C1-C6 alkylsulfonyl group, C1-C6 alkylthio C1-C6 alkyl group, phenyl group and substituted phenyl group having at least one, same or different substituents selected from the group consisting of halogen atom, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group and halo C1-C6 alkylsulfonyl group, C3-C8 alkenylene group, substituted C3-C8 alkenylene group having at least one, same or different substituents selected from the group consisting of halogen atom, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group, halo C1-C6 alkylsulfonyl group, and C1-C6 alkylthio C1-C6 alkyl group, C3-C8 alkynylene group, or substituted C3-C8 alkynylene group having at least one, same or different substituents selected from the group consisting of halogen atom, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group, halo C1-C6 alkylsulfonyl group and C1-C6 alkylthio C1-C6 alkyl group, further, an arbitrary saturated carbon atom in said C1-C8 alkylene group, substituted C1-C8 alkylene group, C3-C8 alkenylene group, substituted C3-C8 alkenylene group, C3-C8 alkynylene group and substituted C3-C8 alkynylene group may be substituted with a C2-C5 alkylene group to form a C3-C6 cycloalkane ring, and arbitrary two carbon atoms in said C1-C8 alkylene group, substituted C1-C8 alkylene group, C3-C8 alkenylene group and substituted C3-C8 alkenylene group may be taken conjointly with an alkylene group or an alkenylene group to form a C3-C6 cycloalkane ring or cycloalkene ring; R1 represents hydrogen atom, mercapto group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C3-C6 cycloalkyl group, halo C3-C6 cycloalkyl group, phenyl group, substituted phenyl group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group, halo C1-C6 alkylsulfonyl group, mono C1-C6 alkylamino group, di C1-C6 alkylamino group in which C1-C6 alkyl groups may be same or different, and C1-C6 alkoxycarbonyl group, phenylthio group, substituted phenylthio group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group, halo C1-C6 alkylsulfonyl group, mono C1-C6 alkylamino group, di C1-C6 alkylamino group in which C1-C6 alkyl groups may be same or different, and C1-C6 alkoxycarbonyl group, heterocyclic group, substituted heterocyclic group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group, halo C1-C6 alkylsulfonyl group, mono C1-C6 alkylamino group, di C1-C6 alkylamino group in which C1-C6 alkyl groups may be same or different, and C1-C6 alkoxycarbonyl group, or —A2—R4 [wherein A2 represents —C(═O)—, —C(═S)—, or —C(═NR5)— (in which R5 represents hydrogen atom, C1-C6 alkyl group, C1-C6 alkoxy group, mono C1-C6 alkylamino group, di C1-C6 alkylamino group in which C1-C6 alkyl groups may be same or different, C1-C6 alkoxycarbonyl group, phenyl group or substituted phenyl group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group and halo C1-C6 alkylsulfonyl group), C1-C8 alkylene group, halo C1-C8 alkylene group, C3-C6 alkenylene group, halo C3-C6 alkenylene group, C3-C6 alkynylene group or halo C3-C6 alkynylene group; and (1) in cases where A2 represents —C(═O)—, —C(═S)— or —C(═NR5)— wherein R5 is as defined above, R4 represents hydrogen atom, C1-C6 alkyl group, halo C1-C6 alkyl group, C3-C6 cycloalkyl group, halo C3-C6 cycloalkyl group, phenyl group, substituted phenyl group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group and halo C1-C6 alkylsulfonyl group, heterocyclic group, substituted heterocyclic group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group and halo C1-C6 alkylsulfonyl group, or —Z1—R6 wherein Z1 represents —O—, —S— or —N(R7)— (wherein R7 represents hydrogen atom, C1-C6 alkyl group, C1-C6 alkylcarbonyl group, halo C1-C6 alkylcarbonyl group or C1-C6 alkoxycarbonyl group), and R6 represents hydrogen atom, C1-C6 alkyl group, halo C1-C6 alkyl group, C3-C6 alkenyl group, halo C3-C6 alkenyl group, C3-C6 alkynyl group, halo C3-C6 alkynyl group, C3-C6 cycloalkyl group, phenyl group, substituted phenyl group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group and halo C1-C6 alkylsulfonyl group, phenyl C1-C4 alkyl group, substituted phenyl C1-C4 alkyl group having, on the ring thereof, at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, cl-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group and halo C1-C6 alkylsulfonyl group, heterocyclic group, or substituted heterocyclic group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group and halo C1-C6 alkylsulfonyl group, and (2) in cases where A2 represents C1-C8 alkylene group, halo C1-C8 alkylene group, C3-C6 alkenylene group, halo C3-C6 alkenylene group, C3-C6 alkynylene group or halo C3-C6 alkynylene group, R4 represents hydrogen atom, halogen atom, cyano group, nitro group, C3-C6 cycloalkyl group, halo C3-C6 cycloalkyl group, C1-C6 alkoxycarbonyl group, mono C1-C6 alkylaminocarbonyl group, di C1-C6 alkylaminocarbonyl group in which C1-C6 alkyl groups may be same or different, phenyl group, substituted phenyl group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group and halo C1-C6 alkylsulfonyl group, heterocyclic group, substituted heterocyclic group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group, and halo C1-C6 alkylsulfonyl group, or —Z2—R8 wherein Z2 represents —O—, —S—, —SO—, —SO2—, —N(R9)— (wherein R9 represents hydrogen atom, C1-C6 alkyl group, C1-C6 alkylcarbonyl group, halo C1-C6 alkylcarbonyl group, C1-C6 alkoxycarbonyl group, phenylcarbonyl group, or substituted phenylcarbonyl group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group and halo C1-C6 alkylsulfonyl group), —C(═O)— or —C(═NOR10)— (wherein R10 represents hydrogen atom, C1-C6 alkyl group, halo C1-C6 alkyl group, C3-C6 alkenyl group, halo C3-C6 alkenyl group, C3-C6 alkynyl group, halo C3-C6 alkynyl group, C3-C6 cycloalkyl group, phenyl C1-C4 alkyl group or substituted phenyl C1-C4 alkyl group having, on the ring thereof, at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group, and halo C1-C6 alkylsulfonyl group) and R8 represents hydrogen atom, C1-C6 alkyl group, halo C1-C6 alkyl group, C3-C6 alkenyl group, halo C3-C6 alkenyl group, C3-C6 alkynyl group, halo C3-C6 alkynyl group, C3-C6 cycloalkyl group, C1-C6 alkylcarbonyl group, halo C1-C6 alkylcarbonyl group, C1-C6 alkoxycarbonyl group, mono C1-C6 alkylaminocarbonyl group, di C1-C6 alkylaminocarbonyl group in which C1-C6 alkyl groups may be same or different, phenyl group, substituted phenyl group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group and halo C1-C6 alkylsulfonyl group, phenyl C1-C4 alkyl group, substituted phenyl C1-C4 alkyl group having, on the ring thereof, at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group and halo C1-C6 alkylsulfonyl group, heterocyclic group, or substituted heterocyclic group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group and halo C1-C6 alkylsulfonyl group], or alternatively, R1 may be combined with A1 to form a 5- to 8-membered ring which may be intercepted by 1 or 2, same or different oxygen atoms, sulfur atoms or nitrogen atoms; R2 and R3 which may be same or different, represent hydrogen atom, C3-C6 cycloalkyl group or —A2—R4 wherein A2 and R4 are as defined above; or alternatively, R2 may be combined with A1 or R1 to form a 5- to 7-membered ring which may be intercepted by 1 or 2, same or different oxygen atoms, sulfur atoms or nitrogen atoms; X which may be same or different, represents halogen atom, cyano group, nitro group, C1-C6 alkyl group, halo C1-C6 alkyl group, C2-C6 alkenyl group, halo C2-C6 alkenyl group, C2-C6 alkynyl group, halo C2-C6 alkynyl group, C3-C6 cycloalkyl group, halo C3-C6 cycloalkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group, halo C1-C6 alkylsulfonyl group, or C1-C6 alkoxycarbonyl group and l represents an integer of 0 to 4; and alternatively, X may be taken conjointly with the adjacent carbon atom on the phenyl ring to form a fused ring, and said fused ring may have at least one, same or different substituents selected from the group consisting of halogen atom, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group and halo C1-C6 alkylsulfonyl group; and Y may be same or different and represents halogen atom, cyano group, nitro group, halo C3-C6 cycloalkyl group, tri C1-C6 alkylsilyl group in which C1-C6 alkyl groups may be same or different, phenyl group, substituted phenyl group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group and halo C1-C6 alkylsulfonyl group, heterocyclic group, substituted heterocyclic group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group and halo C1-C6 alkylsulfonyl group, or —A3—R11 [wherein A3 represents —O—, —S—, —SO—, —SO2—, —C(═O)—, —C(═NOR12)— (in which R12 represents hydrogen atom, C1-C6 alkyl group, halo C1-C6 alkyl group, C3-C6 alkenyl group, halo C3-C6 alkenyl group, C3-C6 alkynyl group, C3-C6 cycloalkyl group, phenyl C1-C4 alkyl group or substituted phenyl C1-C4 alkyl group having, on the ring thereof, at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group, and halo C1-C6 alkylsulfonyl group), C1-C6 alkylene group, halo C1-C6 alkylene group, C2-C6 alkenylene group, halo C2-C6 alkenylene group, C2-C6 alkynylene group or halo C3-C6 alkynylene group; and (1) in cases where A3 represents —O—, —S—, —SO— or —SO2—, R11 represents phenyl group, substituted phenyl group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group, and halo C1-C6 alkylsulfonyl group, heterocyclic group, substituted heterocyclic group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group and halo C1-C6 alkylsulfonyl group, or —A4—R13 (wherein A4 represents C1-C6 alkylene group, halo C1-C6 alkylene group, C3-C6 alkenylene group, halo C3-C6 alkenylene group, C3-C6 alkynylene group or halo C3-C6 alkynylene group, and R13 represents hydrogen atom, halogen atom, C3-C6 cycloalkyl group, halo C3-C6 cycloalkyl group, phenyl group, substituted phenyl group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group, and halo C1-C6 alkylsulfonyl group, or —A5—R14 (wherein A5 represents —O—, —S—, —SO—, —SO2— or —C(═O)—, and R14 represents C1-C6 alkyl group, halo C1-C6 alkyl group, C3-C6 alkenyl group, halo C3-C6 alkenyl group, C3-C6 alkynyl group, halo C3-C6 alkynyl group, C3-C6 cycloalkyl group, halo C3-C6 cycloalkyl group, phenyl group, substituted phenyl group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group and halo C1-C6 alkylsulfonyl group, heterocyclic group, or substituted heterocyclic group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group and halo C1-C6 alkylsulfonyl group)), and (2) in cases where A3 represents —C(═O)— or —C(═NOR12)— wherein R12 is as defined above, R11 represents hydrogen atom, C1-C6 alkyl group, halo C1-C6 alkyl group, C2-C6 alkenyl group, halo C2-C6 alkenyl group, C3-C6 cycloalkyl group, halo C3-C6 cycloalkyl group, C1-C6 alkoxy group, C1-C6 alkylthio group, mono C1-C6 alkylamino group, di C1-C6 alkylamino group in which C1-C6 alkyl groups may be same or different, phenyl group, substituted phenyl group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group and halo C1-C6 alkylsulfonyl group, phenylamino group, substituted phenylamino group having on the ring thereof, at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group and halo C1-C6 alkylsulfonyl group, heterocyclic group, or substituted heterocyclic group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group and halo C1-C6 alkylsulfonyl group, and (3) in cases where A3 represents C1-C6 alkylene group, halo C1-C6 alkylene group, C2-C6 alkenylene group, halo C2-C6 alkenylene group, C2-C6 alkynylene group or halo C3-C6 alkynylene group, R11 represents hydrogen atom, hydroxy group, halogen atom, C3-C6 cycloalkyl group, halo C3-C6 cycloalkyl group, C1-C6 alkoxycarbonyl group, phenyl group, substituted phenyl group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group and halo C1-C6 alkylsulfonyl group, heterocyclic group, substituted heterocyclic group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group and halo C1-C6 alkylsulfonyl group, or —A6—R15 (wherein A6 represents —O—, —S—, —SO— or —SO2—, and R15 represents C3-C6 cycloalkyl group, halo C3-C6 cycloalkyl group, phenyl group, substituted phenyl group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group and halo C1-C6 alkylsulfonyl group, heterocyclic group, substituted heterocyclic group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group and halo C1-C6 alkylsulfonyl group, or —A7—R16 (wherein A7 represents C1-C6 alkylene group, halo C1-C6 alkylene group, C2-C6 alkenylene group, halo C2-C6 alkenylene group, C2-C6 alkynylene group or halo C1-C6 alkynylene group, and R16 represents hydrogen atom, halogen atom, C3-C6 cycloalkyl group, halo C3-C6 cycloalkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group, halo C1-C6 alkylsulfonyl group, phenyl group, substituted phenyl group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group and halo C1-C6 alkylsulfonyl group, phenoxy group, substituted phenoxy group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group and halo C1-C6 alkylsulfonyl group, phenylthio group, substituted phenylthio group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group and halo C1-C6 alkylsulfonyl group, heterocyclic group, or substituted heterocyclic group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group and halo C1-C6 alkylsulfonyl group))] and m represents an integer of 1 to 5; and Y may be taken conjointly with an adjacent carbon atom on the phenyl ring to form a fused ring, and said fused ring may have at least one, same or different substituents selected from the group consisting of halogen atom, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group and halo C1-C6 alkylsulfonyl group; and n represents an integer of 0 to 2.
  • 7. An agrohorticultural insecticide according to claim 6,wherein A1 represents C1-C8 alkylene group, substituted C1-C8 alkylene group having at least one, same or different substituents selected from the group consisting of halogen atom, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group, halo C1-C6 alkylsulfonyl group and C1-C6 alkylthio C1-C6 alkyl group and further, an arbitrary saturated carbon atom in said C1-C8 alkylene group and substituted C1-C8 alkylene group may be substituted with a C2-C5 alkylene group to form a C3-C6 cycloalkane ring, and arbitrary two carbon atoms in said C1-C8 alkylene group and substituted C1-C8 alkylene group may be taken conjointly with an alkylene group or an alkenylene group to form a C3-C6 cycloalkane ring; R1 represents hydrogen atom, mercapto group, C1-C6 alkyl group, halo C1-C6 alkyl group, C3-C6 alkenyl group, halo C3-C6 alkenyl group, C3-C6 alkynyl group, halo C3-C6 alkynyl group, C3-C6 cycloalkyl group, halo C3-C6 cycloalkyl group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkoxy C1-C6 alkyl group, C1-C6 alkylthio C1-C6 alkyl group, mono C1-C6 alkylamino C1-C6 alkyl group, di C1-C6 alkylamino C1-C6 alkyl group in which C1-C6 alkyl groups may be same or different, C1-C6 alkylcarbonyl group, halo C1-C6 alkylcarbonyl group, C1-C6 alkylthiocarbonyl group, C1-C6 alkoxycarbonyl group, mono C1-C6 alkylaminocarbonyl group, di C1-C6 alkylaminocarbonyl group in which C1-C6 alkyl groups may be same or different, mono C1-C6 alkylamino thiocarbonyl group, di C1-C6 alkylamino thiocarbonyl group in which C1-C6 alkyl groups may be same or different, C1-C6 alkylcarbonyl C1-C6 alkyl group, C1-C6 alkoxyimino C1-C6 alkyl group, C1-C6 alkoxycarbonyl C1-C6 alkyl group, mono C1-C6 alkylaminocarbonyl C1-C6 alkyl group, di C1-C6 alkylaminocarbonyl C1-C6 alkyl group in which C1-C6 alkyl groups may be same or different, phenyl group, substituted phenyl group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group, halo C1-C6 alkylsulfonyl group, mono C1-C6 alkylamino group, di C1-C6 alkylamino group in which C1-C6 alkyl groups may be same or different and C1-C6 alkoxycarbonyl group, phenyl C1-C6 alkyl group, substituted phenyl C1-C6 alkyl group having, on the ring thereof, at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group, halo C1-C6 alkylsulfonyl group, mono C1-C6 alkylamino group, di C1-C6 alkylamino group in which C1-C6 alkyl groups may be same or different, and C1-C6 alkoxycarbonyl group, phenylcarbonyl group, substituted phenylcarbonyl group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group, halo C1-C6 alkylsulfonyl group, mono C1-C6 alkylamino group, di C1-C6 alkylamino group in which C1-C6 alkyl groups may be same or different and C1-C6 alkoxycarbonyl group, phenylthio group, substituted phenylthio group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group, halo C1-C6 alkylsulfonyl group, mono C1-C6 alkylamino group, di C1-C6 alkylamino group in which C1-C6 alkyl groups may be same or different and C1-C6 alkoxycarbonyl group, heterocyclic group, or substituted heterocyclic group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group, halo C1-C6 alkylsulfonyl group, mono C1-C6 alkylamino group, di C1-C6 alkylamino group in which C1-C6 alkyl groups may be same or different and C1-C6 alkoxycarbonyl group, or alternatively, R1 may be combined with A1 to form a 5- to 8-membered ring which may be intercepted by 1 or 2, same or different oxygen atoms, sulfur atoms or nitrogen atoms; R2 and R3 which may be same or different, represent hydrogen atom, C1-C6 alkyl group; or alternatively, R2 may be combined with A1 or R1 to form a 5- to 7-membered ring which may be intercepted by 1 or 2, same or different oxygen atoms, sulfur atoms or nitrogen atoms; X which may be same or different, represents halogen atom, nitro group, C1-C6 alkyl group, halo C1-C6 alkyl group, C2-C6 alkenyl group, halo C2-C6 alkenyl group, C2-C6 alkynyl group, halo C2-C6 alkynyl group, C3-C6 cycloalkyl group, halo C3-C6 cycloalkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group or halo C1-C6 alkylsulfonyl group and l represents an integer of 0 to 4; and alternatively, X may be taken conjointly with the adjacent carbon atom on the phenyl ring to form a fused ring, and said fused ring may have at least one, same or different substituents selected from the group consisting of halogen atom, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group and halo C1-C6 alkylsulfonyl group; and Y may be same or different and represents halogen atom, C1-C6 alkyl group, halo C1-C6 alkyl group, hydroxy halo C1-C6 alkyl group, C1-C6 alkoxy halo C1-C6 alkyl group, C1-C6 alkylthio halo C1-C6 alkyl group, C3-C6 alkenyl group, halo C3-C6 alkenyl group, C3-C6 alkynyl group, halo C3-C6 alkynyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkoxy halo C1-C6 alkoxy group, C1-C6 alkylthio halo C1-C6 alkoxy group, halo C1-C6 alkoxy halo C1-C6 alkoxy group, halo C3-C6 alkenyloxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, halo C1-C6 alkoxy halo C1-C6 alkylthio group, halo C1-C6 alkenylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group, halo C1-C6 alkylsulfonyl group, mono C1-C6 alkylamino group, di C1-C6 alkylamino group in which C1-C6 alkyl groups may be same or different, C1-C6 alkoxycarbonyl group, C3-C6 cycloalkyl group, halo C3-C6 cycloalkyl group, phenyl group, substituted phenyl group having at least one, same or different substituents selected from the group consisting of halogen atom, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, halo C1-C6 alkylsulfinyl group, and halo C1-C6 alkylsulfonyl group, phenoxy group, substituted phenoxy group having at least one, same or different substituents selected from the group consisting of halogen atom, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, halo C1-C6 alkylsulfinyl group, and halo C1-C6 alkylsulfonyl group, phenylthio group, substituted phenylthio group having at least one, same or different substituents selected from the group consisting of halogen atom, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, halo C1-C6 alkylsulfinyl group and halo C1-C6 alkylsulfonyl group, pyridyloxy group, substituted pyridyloxy group having at least one, same or different substituents selected from the group consisting of halogen atom, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, halo C1-C6 alkylsulfinyl group and halo C1-C6 alkylsulfonyl group, pyridylthio group, substituted pyridylthio group having at least one, same or different substituents selected from the group consisting of halogen atom, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, halo C1-C6 alkylsulfinyl group and halo C1-C6 alkylsulfonyl group; and m represents an integer of 1 to 5; and Y may be taken conjointly with an adjacent carbon atom on the phenyl ring to form a fused ring, and said fused ring may have at least one, same or different substituents selected from the group consisting of halogen atom, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group and halo C1-C6 alkylsulfonyl group; and n represents an integer of 0 to 2.
  • 8. An agrohorticultural insecticide according to claim 7, wherein A1 represents C1-C8 alkylene group;R1 represents hydrogen atom, C1-C6 alkyl group, halo C1-C6 alkyl group, C3-C6 alkenyl group, C3-C6 alkynyl group, C3-C6 cycloalkyl group, C1-C6 alkylthio group, C1-C6 alkoxy C1-C6 alkyl group, C1-C6 alkylthio C1-C6 alkyl group, C1-C6 alkylcarbonyl group, mono C1-C6 alkylaminocarbonyl group, di C1-C6 alkylaminocarbonyl group in which C1-C6 alkyl groups may be same or different, mono C1-C6 alkylaminothiocarbonyl group, di C1-C6 alkylaminothiocarbonyl group in which C1-C6 alkyl groups may be same or different, C1-C6 alkylcarbonyl C1-C6 alkyl group, C1-C6 alkoxyimino C1-C6 alkyl group, C1-C6 alkoxycarbonyl C1-C6 alkyl group, mono C1-C6 alkylaminocarbonyl C1-C6 alkyl group or di C1-C6 alkylaminocarbonyl C1-C6 alkyl group in which C1-C6 alkyl groups may be same or different; R2 and R3 which may be same or different, represent hydrogen atom or C1-C6 alkyl group; X which may be same or different, represents halogen atom, nitro group, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group or halo C1-C6 alkylsulfonyl group; and l represents an integer of 0 to 4; and alternatively, X may be taken conjointly with the adjacent carbon atom on the phenyl ring to form a fused ring, and said fused ring may have at least one, same or different substituents selected from the group consisting of halogen atom, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group and halo C1-C6 alkylsulfonyl group; Y may be same or different and represents halogen atom, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, halo C1-C6 alkoxy halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group, halo C1-C6 alkylsulfonyl group, substituted phenyl group having at least one, same or different substituents selected from the group consisting of halogen atom, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, halo C1-C6 alkylsulfinyl group and halo C1-C6 alkylsulfonyl group, substituted phenoxy group having at least one, same or different substituents selected from the group consisting of halogen atom, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, halo C1-C6 alkylsulfinyl group and halo C1-C6 alkylsulfonyl group, or substituted pyridyloxy group having at least one, same or different substituents selected from the group consisting of halogen atom, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, halo C1-C6 alkylsulfinyl group and halo C1-C6 alkylsulfonyl group; and m represents an integer of 1 to 5; and Y may be taken conjointly with an adjacent carbon atom on the phenyl ring to form a fused ring, and said fused ring may have at least one, same or different substituents selected from the group consisting of halogen atom, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, halo C1-C6 alkylsulfinyl group and halo C1-C6 alkylsulfonyl group; and n represents an integer of 0 to 2.
  • 9. A method for using an agrohorticultural insecticide, characterized by treating an objective crop or applying to soil in an effective quantity of the agrohorticultural insecticide according to any one of claims 5 to 8 for the purpose of protecting a useful crop.
Priority Claims (2)
Number Date Country Kind
10-340379 Nov 1998 JP
11-234329 Aug 1999 JP
US Referenced Citations (1)
Number Name Date Kind
4732845 Keiji et al. Mar 1988 A
Foreign Referenced Citations (8)
Number Date Country
119428 Sep 1984 DE
3802175 Aug 1989 DE
0 325983 Aug 1989 EP
0365149 Apr 1990 EP
0394126 Oct 1990 EP
0410726 Jan 1991 EP
59 163353 Sep 1984 JP
61 180753 Aug 1986 JP
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