U.S. patent application number 14/628396 was filed with the patent office on 2015-09-10 for composition for noxious organisms-controlling agent and method for using the same.
The applicant listed for this patent is NIHON NOHYAKU CO., LTD.. Invention is credited to Hiroshi KODAMA, Masayuki MORIMOTO, Tetsuyosi NISHIMATSU, Kazuyuki SAKATA.
Application Number | 20150250167 14/628396 |
Document ID | / |
Family ID | 26613737 |
Filed Date | 2015-09-10 |
United States Patent
Application |
20150250167 |
Kind Code |
A1 |
SAKATA; Kazuyuki ; et
al. |
September 10, 2015 |
COMPOSITION FOR NOXIOUS ORGANISMS-CONTROLLING AGENT AND METHOD FOR
USING THE SAME
Abstract
The present invention relates to a composition for noxious
organisms-controlling agent having a synergistic effect and a
method for using said composition, which comprises, as active
ingredients thereof, one or more compounds selected from the
phthalamide derivatives represented by general formula (I) being
useful as an insecticide or acaricide and one or more compounds
selected from the compounds having insecticidal, acaricidal or
nematocidal activity: ##STR00001## wherein R.sup.1, R.sup.2 and
R.sup.3 may be the same or different and each represent hydrogen
atom, C.sub.3-C.sub.6 cycloalkyl, -A.sup.1-Qp, etc., each of X and
Y may be the same or different and represents hydrogen atom,
halogen atom, etc., n is an integer of 1 to 4, m is an integer of 1
to 5, and each of Z.sub.1 and Z.sub.2 represents O or S.
Inventors: |
SAKATA; Kazuyuki;
(Kawachinagano, JP) ; MORIMOTO; Masayuki;
(Kawachinagano, JP) ; KODAMA; Hiroshi; (Hashimoto,
JP) ; NISHIMATSU; Tetsuyosi; (Kawachinagano,
JP) |
|
Applicant: |
Name |
City |
State |
Country |
Type |
NIHON NOHYAKU CO., LTD. |
Tokyo |
|
JP |
|
|
Family ID: |
26613737 |
Appl. No.: |
14/628396 |
Filed: |
February 23, 2015 |
Related U.S. Patent Documents
|
|
|
|
|
|
Application
Number |
Filing Date |
Patent Number |
|
|
13609720 |
Sep 11, 2012 |
|
|
|
14628396 |
|
|
|
|
12068408 |
Feb 6, 2008 |
8329733 |
|
|
13609720 |
|
|
|
|
10475030 |
Oct 16, 2003 |
7361653 |
|
|
PCT/JP02/03780 |
Apr 16, 2002 |
|
|
|
12068408 |
|
|
|
|
Current U.S.
Class: |
514/223.8 ;
514/242; 514/247; 514/274; 514/341; 514/351; 514/352; 514/357;
514/365; 514/374; 514/406; 514/407; 514/427; 514/440; 514/472;
514/616 |
Current CPC
Class: |
A01N 43/54 20130101;
A01N 37/22 20130101; A01N 43/58 20130101; A01N 43/40 20130101; A01N
43/08 20130101; A01N 43/28 20130101; A01N 37/22 20130101; A01N
41/10 20130101; A01N 37/30 20130101; A01N 37/48 20130101; A01N
41/10 20130101; A01N 41/10 20130101; A01N 37/18 20130101; A01N
37/22 20130101; A01N 43/76 20130101; A01N 43/88 20130101; A01N
37/48 20130101; A01N 43/58 20130101; A01N 37/30 20130101; A01N
47/38 20130101; A01N 2300/00 20130101; A01N 47/34 20130101; A01N
31/14 20130101; A01N 55/00 20130101; A01N 43/88 20130101; A01N
43/12 20130101; A01N 43/56 20130101; A01N 47/36 20130101; A01N
43/36 20130101; A01N 43/707 20130101; A01N 2300/00 20130101; A01N
43/88 20130101; A01N 37/28 20130101; A01N 51/00 20130101; A01N
43/707 20130101; A01N 43/56 20130101; A01N 43/50 20130101; A01N
47/40 20130101; A01N 51/00 20130101; A01N 59/16 20130101; A01N
57/16 20130101; A01N 43/58 20130101; A01N 43/20 20130101; A01N
43/88 20130101; A01N 43/58 20130101; A01N 43/90 20130101; A01N
37/28 20130101; A01N 43/707 20130101; A01N 51/00 20130101; A01N
43/28 20130101; A01N 2300/00 20130101; A01N 43/36 20130101; A01N
37/28 20130101; A01N 47/24 20130101; A01N 53/00 20130101; A01N
57/28 20130101; A01N 27/00 20130101; A01N 43/36 20130101; A01N
63/00 20130101; A01N 47/40 20130101; A01N 61/00 20130101; A01N
43/28 20130101; A01N 57/32 20130101; A01N 55/04 20130101; A01N
2300/00 20130101; A01N 37/22 20130101; A01N 43/56 20130101; A01N
37/30 20130101; A01N 43/36 20130101; A01N 37/48 20130101; A01N
43/56 20130101; A01N 43/78 20130101 |
International
Class: |
A01N 37/30 20060101
A01N037/30; A01N 43/28 20060101 A01N043/28; A01N 37/18 20060101
A01N037/18; A01N 43/88 20060101 A01N043/88; A01N 43/58 20060101
A01N043/58; A01N 43/76 20060101 A01N043/76; A01N 43/36 20060101
A01N043/36; A01N 43/707 20060101 A01N043/707; A01N 43/40 20060101
A01N043/40; A01N 43/54 20060101 A01N043/54; A01N 43/08 20060101
A01N043/08; A01N 43/78 20060101 A01N043/78; A01N 43/56 20060101
A01N043/56; A01N 43/50 20060101 A01N043/50 |
Foreign Application Data
Date |
Code |
Application Number |
Apr 17, 2001 |
JP |
2001-118840 |
Apr 26, 2001 |
JP |
2001-129588 |
Claims
1. A composition for noxious organisms-controlling agent
comprising, as active ingredients thereof, one or more compounds
selected from phthalamide derivatives represented by general
formula (I): ##STR00004## wherein R.sup.1, R.sup.2 and R.sup.3,
which may be the same or different, each represent a hydrogen atom,
a C.sub.3-C.sub.6 cycloalkyl group, a halo C.sub.3-C.sub.6
cycloalkyl group or -A.sup.1-Q.sub.p (in this formula, A.sup.1
represents a C.sub.1-C.sub.8 alkylene group, a C.sub.3-C.sub.6
alkenylene group or a C.sub.3-C.sub.6 alkynylene group; Q
represents a hydrogen atom; a halogen atom; a cyano group; a nitro
group; a halo C.sub.1-C.sub.6 alkyl group; a C.sub.3-C.sub.6
cycloalkyl group; a halo C.sub.3-C.sub.6 cycloalkyl group; a
C.sub.1-C.sub.6 alkoxycarbonyl group; a di C.sub.1-C.sub.6
alkoxyphosphoryl group in which the alkoxy groups may be the same
or different; a di C.sub.1-C.sub.6 alkoxythiophosphoryl group in
which the alkoxy groups may be the same or different; a
diphenylphosphino group; a diphenylphosphono group; a phenyl group;
a substituted phenyl group having at least one, the same or
different substituents selected from the group consisting of
halogen atom, C.sub.1-C.sub.6 alkyl group, halo C.sub.1-C.sub.6
alkyl group, C.sub.1-C.sub.6 alkoxy group, halo C.sub.1-C.sub.6
alkoxy group, C.sub.1-C.sub.6 alkylthio group, halo C.sub.1-C.sub.6
alkylthio group, C.sub.1-C.sub.6 alkylsulfinyl group, halo
C.sub.1-C.sub.6 alkylsulfinyl group, C.sub.1-C.sub.6 alkylsulfonyl
group and halo C.sub.1-C.sub.6 alkylsulfonyl group; a heterocyclic
group (the term heterocyclic group means a pyridyl group, a
pyridine-N-oxide group, a pyrimidinyl group, a furyl group, a
tetrahydrofuryl group, a thienyl group, a tetrahydrothienyl group,
a tetrahydropyranyl group, a tetrahydrothiopyranyl group, an
oxazolyl group, an isoxazolyl group, an oxadiazolyl group, a
thiazolyl group, an isothiazolyl group, a thiadiazolyl group, an
imidazolyl group, a triazolyl group or a pyrazolyl group); a
substituted heterocyclic group (the term heterocyclic group is as
defined above) having at least one, the same or different
substituents selected from the group consisting of halogen atom,
C.sub.1-C.sub.6 alkyl group, halo C.sub.1-C.sub.6 alkyl group,
C.sub.1-C.sub.6 alkoxy group, halo C.sub.1-C.sub.6 alkoxy group,
C.sub.1-C.sub.6 alkylthio group, halo C.sub.1-C.sub.6 alkylthio
group, C.sub.1-C.sub.6 alkylsulfinyl group, halo C.sub.1-C.sub.6
alkylsulfinyl group, C.sub.1-C.sub.6 alkylsulfonyl group and halo
C.sub.1-C.sub.6 alkylsulfonyl group; or --Z.sup.3--R.sup.4 (in this
formula, Z.sup.3 represents --O--, --S--, --SO--, --SO.sub.2-- or
--N(R.sup.5)-- (in this formula, R.sup.5 represents a hydrogen
atom; a C.sub.1-C.sub.6 alkylcarbonyl group; a halo C.sub.1-C.sub.6
alkylcarbonyl group; a C.sub.1-C.sub.6 alkoxycarbonyl group; a
phenylcarbonyl group; a substituted phenylcarbonyl group having at
least one, the same or different substituents selected from the
group consisting of halogen atom, C.sub.1-C.sub.6 alkyl group, halo
C.sub.1-C.sub.6 alkyl group, C.sub.1-C.sub.6 alkoxy group, halo
C.sub.1-C.sub.6 alkoxy group, C.sub.1-C.sub.6 alkylthio group, halo
C.sub.1-C.sub.6 alkylthio group, C.sub.1-C.sub.6 alkylsulfinyl
group, halo C.sub.1-C.sub.6 alkylsulfinyl group, C.sub.1-C.sub.6
alkylsulfonyl group and halo C.sub.1-C.sub.6 alkylsulfonyl group; a
phenyl C.sub.1-C.sub.4 alkoxycarbonyl group; or a substituted
phenyl C.sub.1-C.sub.4 alkoxycarbonyl group having, on the ring
thereof, at least one, the same or different substituents selected
from the group consisting of halogen atom, C.sub.1-C.sub.6 alkyl
group, halo C.sub.1-C.sub.6 alkyl group, C.sub.1-C.sub.6 alkoxy
group, halo C.sub.1-C.sub.6 alkoxy group, C.sub.1-C.sub.6 alkylthio
group, halo C.sub.1-C.sub.6 alkylthio group, C.sub.1-C.sub.6
alkylsulfinyl group, halo C.sub.1-C.sub.6 alkylsulfinyl group,
C.sub.1-C.sub.6 alkylsulfonyl group and halo C.sub.1-C.sub.6
alkylsulfonyl group), and R.sup.4 represents a hydrogen atom; a
C.sub.1-C.sub.6 alkyl group; a halo C.sub.1-C.sub.6 alkyl group; a
C.sub.3-C.sub.6 alkenyl group; a halo C.sub.3-C.sub.6 alkenyl
group; a C.sub.3-C.sub.6 alkynyl group; a halo C.sub.3-C.sub.6
alkynyl group; a C.sub.3-C.sub.6 cycloalkyl group; a halo
C.sub.3-C.sub.6 cycloalkyl group; a C.sub.1-C.sub.6 alkylcarbonyl
group; a halo C.sub.1-C.sub.6 alkylcarbonyl group; a
C.sub.1-C.sub.6 alkoxycarbonyl group; a phenyl group; a substituted
phenyl group having at least one, the same or different
substituents selected from the group consisting of halogen atom,
C.sub.1-C.sub.6 alkyl group, halo C.sub.1-C.sub.6 alkyl group,
C.sub.1-C.sub.6 alkoxy group, halo C.sub.1-C.sub.6 alkoxy group,
C.sub.1-C.sub.6 alkylthio group, halo C.sub.1-C.sub.6 alkylthio
group, C.sub.1-C.sub.6 alkylsulfinyl group, halo C.sub.1-C.sub.6
alkylsulfinyl group, C.sub.1-C.sub.6 alkylsulfonyl group and halo
C.sub.1-C.sub.6 alkylsulfonyl group; a phenyl C.sub.1-C.sub.4 alkyl
group; a substituted phenyl C.sub.1-C.sub.4 alkyl group having, on
the ring thereof, at least one, the same or different substituents
selected from the group consisting of halogen atom, C.sub.1-C.sub.6
alkyl group, halo C.sub.1-C.sub.6 alkyl group, C.sub.1-C.sub.6
alkoxy group, halo C.sub.1-C.sub.6 alkoxy group, C.sub.1-C.sub.6
alkylthio group, halo C.sub.1-C.sub.6 alkylthio group,
C.sub.1-C.sub.6 alkylsulfinyl group, halo C.sub.1-C.sub.6
alkylsulfinyl group, C.sub.1-C.sub.6 alkylsulfonyl group and halo
C.sub.1-C.sub.6 alkylsulfonyl group; a heterocyclic group (the term
heterocyclic group is as defined above); or a substituted
heterocyclic group (the term heterocyclic group is as defined
above) having at least one, the same or different substituents
selected from the group consisting of halogen atom, C.sub.1-C.sub.6
alkyl group, halo C.sub.1-C.sub.6 alkyl group, C.sub.1-C.sub.6
alkoxy group, halo C.sub.1-C.sub.6 alkoxy group, C.sub.1-C.sub.6
alkylthio group, halo C.sub.1-C.sub.6 alkylthio group,
C.sub.1-C.sub.6 alkylsulfinyl group, halo C.sub.1-C.sub.6
alkylsulfinyl group, C.sub.1-C.sub.6 alkylsulfonyl group and halo
C.sub.1-C.sub.6 alkylsulfonyl group); and p represents an integer
of 1-4); and R.sup.1 and R.sup.2 may be taken conjointly to form a
4- to 7-membered ring which may be interrupted by one to three, the
same or different hetero atoms selected from oxygen atom, sulfur
atom or nitrogen atom; X may be the same or different and
represents a hydrogen atom; a halogen atom; a cyano group; a nitro
group; a C.sub.3-C.sub.6 cycloalkyl group; a halo C.sub.3-C.sub.6
cycloalkyl group; a phenyl group; a substituted phenyl group having
at least one, the same or different substituents selected from the
group consisting of halogen atom, C.sub.1-C.sub.6 alkyl group, halo
C.sub.1-C.sub.6 alkyl group, C.sub.1-C.sub.6 alkoxy group, halo
C.sub.1-C.sub.6 alkoxy group, C.sub.1-C.sub.6 alkylthio group, halo
C.sub.1-C.sub.6 alkylthio group, C.sub.1-C.sub.6 alkylsulfinyl
group, halo C.sub.1-C.sub.6 alkylsulfinyl group, C.sub.1-C.sub.6
alkylsulfonyl group and halo C.sub.1-C.sub.6 alkylsulfonyl group; a
heterocyclic group (the term heterocyclic group is as defined
above); a substituted heterocyclic group (the term heterocyclic
group is as defined above) having at least one, the same or
different substituents selected from the group consisting of
halogen atom, C.sub.1-C.sub.6 alkyl group, halo C.sub.1-C.sub.6
alkyl group, C.sub.1-C.sub.6 alkoxy group, halo C.sub.1-C.sub.6
alkoxy group, C.sub.1-C.sub.6 alkylthio group, halo C.sub.1-C.sub.6
alkylthio group, C.sub.1-C.sub.6 alkylsulfinyl group, halo
C.sub.1-C.sub.6 alkylsulfinyl group, C.sub.1-C.sub.6 alkylsulfonyl
group and halo C.sub.1-C.sub.6 alkylsulfonyl group; or
-A.sup.2-R.sup.6 (in this formula, A.sup.2 represents --O--, --S--,
--SO--, --SO.sub.2--, --C(.dbd.O)--, --C(.dbd.NOR.sup.7)-- (in this
formula, R.sup.7 represents a hydrogen atom, a C.sub.1-C.sub.6
alkyl group, a halo C.sub.1-C.sub.6 alkyl group, a C.sub.3-C.sub.6
alkenyl group, a halo C.sub.3-C.sub.6 alkenyl group, a
C.sub.3-C.sub.6 alkynyl group, a cyclo C.sub.3-C.sub.6 alkyl group,
a phenyl C.sub.1-C.sub.4 alkyl group or a substituted phenyl
C.sub.1-C.sub.4 alkyl group having, on the ring thereof, at least
one, the same or different substituents selected from the group
consisting of halogen atom, C.sub.1-C.sub.6 alkyl group, halo
C.sub.1-C.sub.6 alkyl group, C.sub.1-C.sub.6 alkoxy group, halo
C.sub.1-C.sub.6 alkoxy group, C.sub.1-C.sub.6 alkylthio group, halo
C.sub.1-C.sub.6 alkylthio group, C.sub.1-C.sub.6 alkylsulfinyl
group, halo C.sub.1-C.sub.6 alkylsulfinyl group, C.sub.1-C.sub.6
alkylsulfonyl group and halo C.sub.1-C.sub.6 alkylsulfonyl group),
a C.sub.1-C.sub.6 alkylene group, a halo C.sub.1-C.sub.6 alkylene
group, a C.sub.2-C.sub.6 alkenylene group, a halo C.sub.2-C.sub.6
alkenylene group, a C.sub.2-C.sub.6 alkynylene group or a halo
C.sub.3-C.sub.6 alkynylene group, and (1) in a case where A.sup.2
represents --O--, --S--, --SO-- or --SO.sub.2--, R.sup.6 represents
a halo C.sub.3-C.sub.6 cycloalkyl group; a halo C.sub.3-C.sub.6
cycloalkenyl group; a phenyl group; a substituted phenyl group
having at least one, the same or different substituents selected
from the group consisting of halogen atom, C.sub.1-C.sub.6 alkyl
group, halo C.sub.1-C.sub.6 alkyl group, C.sub.1-C.sub.6 alkoxy
group, halo C.sub.1-C.sub.6 alkoxy group, C.sub.1-C.sub.6 alkylthio
group, halo C.sub.1-C.sub.6 alkylthio group, C.sub.1-C.sub.6
alkylsulfinyl group, halo C.sub.1-C.sub.6 alkylsulfinyl group,
C.sub.1-C.sub.6 alkylsulfonyl group and halo C.sub.1-C.sub.6
alkylsulfonyl group; a heterocyclic group (the term heterocyclic
group is as defined above); a substituted heterocyclic group (the
term heterocyclic group is as defined above) having at least one,
the same or different substituents selected from the group
consisting of halogen atom, C.sub.1-C.sub.6 alkyl group, halo
C.sub.1-C.sub.6 alkyl group, C.sub.1-C.sub.6 alkoxy group, halo
C.sub.1-C.sub.6 alkoxy group, C.sub.1-C.sub.6 alkylthio group, halo
C.sub.1-C.sub.6 alkylthio group, C.sub.1-C.sub.6 alkylsulfinyl
group, halo C.sub.1-C.sub.6 alkylsulfinyl group, C.sub.1-C.sub.6
alkylsulfonyl group and halo C.sub.1-C.sub.6 alkylsulfonyl group;
or -A.sup.3-R.sup.8 (in this formula, A.sup.3 represents a
C.sub.1-C.sub.6 alkylene group, a halo C.sub.1-C.sub.6 alkylene
group, a C.sub.3-C.sub.6 alkenylene group, a halo C.sub.3-C.sub.6
alkenylene group, a C.sub.3-C.sub.6 alkynylene group or a halo
C.sub.3-C.sub.6 alkynylene group, and R.sup.8 represents a hydrogen
atom; a halogen atom; a C.sub.3-C.sub.6 cycloalkyl group; a halo
C.sub.3-C.sub.6 cycloalkyl group; a C.sub.1-C.sub.6 alkoxycarbonyl
group; a phenyl group; a substituted phenyl group having at least
one, the same or different substituents selected from the group
consisting of halogen atom, C.sub.1-C.sub.6 alkyl group, halo
C.sub.1-C.sub.6 alkyl group, C.sub.1-C.sub.6 alkoxy group, halo
C.sub.1-C.sub.6 alkoxy group, C.sub.1-C.sub.6 alkylthio group, halo
C.sub.1-C.sub.6 alkylthio group, C.sub.1-C.sub.6 alkylsulfinyl
group, halo C.sub.1-C.sub.6 alkylsulfinyl group, C.sub.1-C.sub.6
alkylsulfonyl group and halo C.sub.1-C.sub.6 alkylsulfonyl group;
or -A.sup.4-R.sup.9 (in this formula, A.sup.4 represents --O--,
--S--, --SO--, --SO.sub.2-- or --C(.dbd.O), and R.sup.9 represents
a C.sub.1-C.sub.6 alkyl group; a halo C.sub.1-C.sub.6 alkyl group;
a C.sub.3-C.sub.6 alkenyl group; a halo C.sub.3-C.sub.6 alkenyl
group; a C.sub.3-C.sub.6 cycloalkyl group; a halo C.sub.3-C.sub.6
cycloalkyl group; a phenyl group; a substituted phenyl group having
at least one, the same or different substituents selected from the
group consisting of halogen atom, C.sub.1-C.sub.6 alkyl group, halo
C.sub.1-C.sub.6 alkyl group, C.sub.1-C.sub.6 alkoxy group, halo
C.sub.1-C.sub.6 alkoxy group, C.sub.1-C.sub.6 alkylthio group, halo
C.sub.1-C.sub.6 alkylthio group, C.sub.1-C.sub.6 alkylsulfinyl
group, halo C.sub.1-C.sub.6 alkylsulfinyl group, C.sub.1-C.sub.6
alkylsulfonyl group and halo C.sub.1-C.sub.6 alkylsulfonyl group; a
heterocyclic group (the term heterocyclic group is as defined
above); or a substituted heterocyclic group (the term heterocyclic
group is as defined above) having at least one, the same or
different substituents selected from the group consisting of
halogen atom, C.sub.1-C.sub.6 alkyl group, halo C.sub.1-C.sub.6
alkyl group, C.sub.1-C.sub.6 alkoxy group, halo C.sub.1-C.sub.6
alkoxy group, C.sub.1-C.sub.6 alkylthio group, halo C.sub.1-C.sub.6
alkylthio group, C.sub.1-C.sub.6 alkylsulfinyl group, halo
C.sub.1-C.sub.6 alkylsulfinyl group, C.sub.1-C.sub.6 alkylsulfonyl
group and halo C.sub.1-C.sub.6 alkylsulfonyl group)), (2) in a case
where A.sup.2 represents --C(.dbd.O)-- or --C(.dbd.NOR.sup.7)-- (in
this formula, R.sup.7 is as defined above), R.sup.6 represents a
C.sub.1-C.sub.6 alkyl group; a halo C.sub.1-C.sub.6 alkyl group; a
C.sub.2-C.sub.6 alkenyl group; a halo C.sub.2-C.sub.6 alkenyl
group; a C.sub.3-C.sub.6 cycloalkyl group; a halo C.sub.3-C.sub.6
cycloalkyl group; a C.sub.1-C.sub.6 alkoxy group; a C.sub.1-C.sub.6
alkylthio group; a mono C.sub.1-C.sub.6 alkylamino group; a di
C.sub.1-C.sub.6 alkylamino group in which the alkyl groups may be
the same or different; a phenyl group; a substituted phenyl group
having at least one, the same or different substituents selected
from the group consisting of halogen atom, C.sub.1-C.sub.6 alkyl
group, halo C.sub.1-C.sub.6 alkyl group, C.sub.1-C.sub.6 alkoxy
group, halo C.sub.1-C.sub.6 alkoxy group, C.sub.1-C.sub.6 alkylthio
group, halo C.sub.1-C.sub.6 alkylthio group, C.sub.1-C.sub.6
alkylsulfinyl group, halo C.sub.1-C.sub.6 alkylsulfinyl group,
C.sub.1-C.sub.6 alkylsulfonyl group and halo C.sub.1-C.sub.6
alkylsulfonyl group; a phenylamino group; a substituted phenylamino
group having, on the ring thereof, at least one, the same or
different substituents selected from the group consisting of
halogen atom, C.sub.1-C.sub.6 alkyl group, halo C.sub.1-C.sub.6
alkyl group, C.sub.1-C.sub.6 alkoxy group, halo C.sub.1-C.sub.6
alkoxy group, C.sub.1-C.sub.6 alkylthio group, halo C.sub.1-C.sub.6
alkylthio group, C.sub.1-C.sub.6 alkylsulfinyl group, halo
C.sub.1-C.sub.6 alkylsulfinyl group, C.sub.1-C.sub.6 alkylsulfonyl
group and halo C.sub.1-C.sub.6 alkylsulfonyl group; a heterocyclic
group (the term heterocyclic group is as defined above); or a
substituted heterocyclic group (the term heterocyclic group is as
defined above) having at least one, the same or different
substituents selected from the group consisting of halogen atom,
C.sub.1-C.sub.6 alkyl group, halo C.sub.1-C.sub.6 alkyl group,
C.sub.1-C.sub.6 alkoxy group, halo C.sub.1-C.sub.6 alkoxy group,
C.sub.1-C.sub.6 alkylthio group, halo C.sub.1-C.sub.6 alkylthio
group, C.sub.1-C.sub.6 alkylsulfinyl group, halo C.sub.1-C.sub.6
alkylsulfinyl group, C.sub.1-C.sub.6 alkylsulfonyl group and halo
C.sub.1-C.sub.6 alkylsulfonyl group, and (3) in a case where
A.sup.2 represents a C.sub.1-C.sub.6 alkylene group, a halo C
.sub.1-C.sub.6 alkylene group, a C.sub.2-C.sub.6 alkenylene group,
a halo C.sub.2-C.sub.6 alkenylene group, a C.sub.2-C.sub.6
alkynylene group or a halo C.sub.3-C.sub.6 alkynylene group,
R.sup.6 represents a hydrogen atom; a halogen atom; a
C.sub.3-C.sub.6 cycloalkyl group; a halo C.sub.3-C.sub.6 cycloalkyl
group; a C.sub.1-C.sub.6 alkoxycarbonyl group; a phenyl group; a
substituted phenyl group having at least one, the same or different
substituents selected from the group consisting of halogen atom,
C.sub.1-C.sub.6 alkyl group, halo C.sub.1-C.sub.6 alkyl group,
C.sub.1-C.sub.6 alkoxy group, halo C.sub.1-C.sub.6 alkoxy group,
C.sub.1-C.sub.6 alkylthio group, halo C.sub.1-C.sub.6 alkylthio
group, C.sub.1-C.sub.6 alkylsulfinyl group, halo C.sub.1-C.sub.6
alkylsulfinyl group, C.sub.1-C.sub.6 alkylsulfonyl group and halo
C.sub.1-C.sub.6 alkylsulfonyl group; a heterocyclic group (the term
heterocyclic group is as defined above); a substituted heterocyclic
group (the term heterocyclic group is as defined above) having at
least one, the same or different substituents selected from the
group consisting of halogen atom, C.sub.1-C.sub.6 alkyl group, halo
C.sub.1-C.sub.6 alkyl group, C.sub.1-C.sub.6 alkoxy group, halo
C.sub.1-C.sub.6 alkoxy group, C.sub.1-C.sub.6 alkylthio group, halo
C.sub.1-C.sub.6 alkylthio group, C.sub.1-C.sub.6 alkylsulfinyl
group, halo C.sub.1-C.sub.6 alkylsulfinyl group, C.sub.1-C.sub.6
alkylsulfonyl group and halo C.sub.1-C.sub.6 alkylsulfonyl group;
or -A.sup.5-R.sup.10 (in this formula, A.sup.5 represents --O--,
--S--, --SO-- or --SO.sub.2--, and R.sup.10 represents a
C.sub.3-C.sub.6 cycloalkyl group; a halo C.sub.3-C.sub.6 cycloalkyl
group; a phenyl group; a substituted phenyl group having at least
one, the same or different substituents selected from the group
consisting of halogen atom, C.sub.1-C.sub.6 alkyl group, halo
C.sub.1-C.sub.6 alkyl group, C.sub.1-C.sub.6 alkoxy group, halo
C.sub.1-C.sub.6 alkoxy group, C.sub.1-C.sub.6 alkylthio group, halo
C.sub.1-C.sub.6 alkylthio group, C.sub.1-C.sub.6 alkylsulfinyl
group, halo C.sub.1-C.sub.6 alkylsulfinyl group, C.sub.1-C.sub.6
alkylsulfonyl group and halo C.sub.1-C.sub.6 alkylsulfonyl group; a
heterocyclic group (the term heterocyclic group is as defined
above); a substituted heterocyclic group (the term heterocyclic
group is as defined above) having at least one, the same or
different substituents selected from the group consisting of
halogen atom, C.sub.1-C.sub.6 alkyl group, halo C.sub.1-C.sub.6
alkyl group, C.sub.1-C.sub.6 alkoxy group, halo C.sub.1-C.sub.6
alkoxy group, C.sub.1-C.sub.6 alkylthio group, halo C.sub.1-C.sub.6
alkylthio group, C.sub.1-C.sub.6 alkylsulfinyl group, halo
C.sub.1-C.sub.6 alkylsulfinyl group, C.sub.1-C.sub.6 alkylsulfonyl
group and halo C.sub.1-C.sub.6 alkylsulfonyl group; or
-A.sup.6-R.sup.11 (in this formula, A.sup.6 represents a
C.sub.1-C.sub.6 alkylene group; a halo C.sub.1-C.sub.6 alkylene
group; a C.sub.2-C.sub.6 alkenylene group; a halo C.sub.2-C.sub.6
alkenylene group; a C.sub.2-C.sub.6 alkynylene group; or a halo
C.sub.3-C.sub.6 alkynylene group; and R.sup.11 represents a
hydrogen atom; a halogen atom; a C.sub.3-C.sub.6 cycloalkyl group;
a halo C.sub.3-C.sub.6 cycloalkyl group; a C.sub.1-C.sub.6 alkoxy
group; a halo C.sub.1-C.sub.6 alkoxy group; a C.sub.1-C.sub.6
alkylthio group; a halo C.sub.1-C.sub.6 alkylthio group; a
C.sub.1-C.sub.6 alkylsulfinyl group; a halo C.sub.1-C.sub.6
alkylsulfinyl group; a C.sub.1-C.sub.6 alkylsulfonyl group; a halo
C.sub.1-C.sub.6 alkylsulfonyl group; a phenyl group; a substituted
phenyl group having at least one, the same or different
substituents selected from the group consisting of halogen atom,
C.sub.1-C.sub.6 alkyl group, halo C.sub.1-C.sub.6 alkyl group,
C.sub.1-C.sub.6 alkoxy group, halo C.sub.1-C.sub.6 alkoxy group,
C.sub.1-C.sub.6 alkylthio group, halo C.sub.1-C.sub.6 alkylthio
group, C.sub.1-C.sub.6 alkylsulfinyl group, halo C.sub.1-C.sub.6
alkylsulfinyl group, C.sub.1-C.sub.6 alkylsulfonyl group and halo
C.sub.1-C.sub.6 alkylsulfonyl group; a phenoxy group; a substituted
phenoxy group having at least one, the same or different
substituents selected from the group consisting of halogen atom,
C.sub.1-C.sub.6 alkyl group, halo C.sub.1-C.sub.6 alkyl group,
C.sub.1-C.sub.6 alkoxy group, halo C.sub.1-C.sub.6 alkoxy group,
C.sub.1-C.sub.6 alkylthio group, halo C.sub.1-C.sub.6 alkylthio
group, C.sub.1-C.sub.6 alkylsulfinyl group, halo C.sub.1-C.sub.6
alkylsulfinyl group, C.sub.1-C.sub.6 alkylsulfonyl group and halo
C.sub.1-C.sub.6 alkylsulfonyl group; a phenylthio group; a
substituted phenylthio group having at least one, the same or
different substituents selected from the group consisting of
halogen atom, C.sub.1-C.sub.6 alkyl group, halo C.sub.1-C.sub.6
alkyl group, C.sub.1-C.sub.6 alkoxy group, halo C.sub.1-C.sub.6
alkoxy group, C.sub.1-C.sub.6 alkylthio group, halo C.sub.1-C.sub.6
alkylthio group, C.sub.1-C.sub.6 alkylsulfinyl group, halo
C.sub.1-C.sub.6 alkylsulfinyl group, C.sub.1-C.sub.6 alkylsulfonyl
group and halo C.sub.1-C.sub.6 alkylsulfonyl group; a heterocyclic
group (the term heterocyclic group is as defined above; or a
substituted heterocyclic group (the term heterocyclic group is as
defined above) having at least one, the same or different
substituents selected from the group consisting of halogen atom,
C.sub.1-C.sub.6 alkyl group, halo C.sub.1-C.sub.6 alkyl group,
C.sub.1-C.sub.6 alkoxy group, halo C.sub.1-C.sub.6 alkoxy group,
C.sub.1-C.sub.6 alkylthio group, halo C.sub.1-C.sub.6 alkylthio
group, C.sub.1-C.sub.6 alkylsulfinyl group, halo C.sub.1-C.sub.6
alkylsulfinyl group, C.sub.1-C.sub.6 alkylsulfonyl group and halo
C.sub.1-C.sub.6 alkylsulfonyl group))), and n represents an integer
of 1-4; and X may be taken conjointly together with an adjacent
carbon atom on the phenyl ring to form a condensed ring (the term
condensed ring means naphthalene, tetrahydronaphthalene, indene,
indane, quinoline, quinazoline, chromane, isochromane, indole,
indoline, benzodioxane, benzodioxole, benzofuran,
dihydrobenzofuran, benzothiophene, dihydrobenzothiophene,
benzoxazole, benzothiazole, benzimidazole or indazole), and said
condensed ring may have at least one, the same or different
substituents selected from the group consisting of halogen atom,
C.sub.1-C.sub.6 alkyl group, halo C.sub.1-C.sub.6 alkyl group,
C.sub.1-C.sub.6 alkoxy group, halo C.sub.1-C.sub.6 alkoxy group,
C.sub.1-C.sub.6 alkylthio group, halo C.sub.1-C.sub.6 alkylthio
group, C.sub.1-C.sub.6 alkylsulfinyl group, halo C.sub.1-C.sub.6
alkylsulfinyl group, C.sub.1-C.sub.6 alkylsulfonyl group, halo
C.sub.1-C.sub.6 alkylsulfonyl group, phenyl group, substituted
phenyl group having at least one, the same or different
substituents selected from the group consisting of halogen atom,
C.sub.1-C.sub.6 alkyl group, halo C.sub.1-C.sub.6 alkyl group,
C.sub.1-C.sub.6 alkoxy group, halo C.sub.1-C.sub.6 alkoxy group,
C.sub.1-C.sub.6 alkylthio group, halo C.sub.1-C.sub.6 alkylthio
group, C.sub.1-C.sub.6 alkylsulfinyl group, halo C.sub.1-C.sub.6
alkylsulfinyl group, C.sub.1-C.sub.6 alkylsulfonyl group and halo
C.sub.1-C.sub.6 alkylsulfonyl group, heterocyclic group (the term
heterocyclic group is as defined above) and substituted
heterocyclic group (the term heterocyclic group is as defined
above) having at least one, the same or different substituents
selected from the group consisting of halogen atom, C.sub.1-C.sub.6
alkyl group, halo C.sub.1-C.sub.6 alkyl group, C.sub.1-C.sub.6
alkoxy group, halo C.sub.1-C.sub.6 alkoxy group, C.sub.1-C.sub.6
alkylthio group, halo C.sub.1-C.sub.6 alkylthio group,
C.sub.1-C.sub.6 alkylsulfinyl group, halo C.sub.1-C.sub.6
alkylsulfinyl group, C.sub.1-C.sub.6 alkylsulfonyl group and halo
C.sub.1-C.sub.6 alkylsulfonyl group; and Y may be the same or
different and represents a hydrogen atom; a halogen atom; a cyano
group; a nitro group; a halo C.sub.3-C.sub.6 cycloalkyl group; a
phenyl group; a substituted phenyl group having at least one, the
same or different substituents selected from the group consisting
of halogen atom, C.sub.1-C.sub.6 alkyl group, halo C.sub.1-C.sub.6
alkyl group, C.sub.1-C.sub.6 alkoxy group, halo C.sub.1-C.sub.6
alkoxy group, C.sub.1-C.sub.6 alkylthio group, halo C.sub.1-C.sub.6
alkylthio group, C.sub.1-C.sub.6 alkylsulfinyl group, halo
C.sub.1-C.sub.6 alkylsulfinyl group, C.sub.1-C.sub.6 alkylsulfonyl
group and halo C.sub.1-C.sub.6 alkylsulfonyl group; a heterocyclic
group (the term heterocyclic group is as defined above); a
substituted heterocyclic group (the term heterocyclic group is as
defined above) having at least one, the same or different
substituents selected from the group consisting of halogen atom,
C.sub.1-C.sub.6 alkyl group, halo C.sub.1-C.sub.6 alkyl group,
C.sub.1-C.sub.6 alkoxy group, halo C.sub.1-C.sub.6 alkoxy group,
C.sub.1-C.sub.6 alkylthio group, halo C.sub.1-C.sub.6 alkylthio
group, C.sub.1-C.sub.6 alkylsulfinyl group, halo C.sub.1-C.sub.6
alkylsulfinyl group, C.sub.1-C.sub.6 alkylsulfonyl group and halo
C.sub.1-C.sub.6 alkylsulfonyl group; or -A.sup.2-R.sup.6 (in this
formula, A.sup.2 and R.sup.6 are as defined above); and m
represents an integer of 1-5; and Y may be taken conjointly
together with an adjacent carbon atom on the phenyl ring to form a
condensed ring (the term condensed ring is as defined above), and
said condensed ring may have at least one, the same or different
substituents selected from the group consisting of halogen atom,
C.sub.1-C.sub.6 alkyl group, halo C.sub.1-C.sub.6 alkyl group,
C.sub.1-C.sub.6 alkoxy group, halo C.sub.1-C.sub.6 alkoxy group,
C.sub.1-C.sub.6 alkylthio group, halo C.sub.1-C.sub.6 alkylthio
group, C.sub.1-C.sub.6 alkylsulfinyl group, halo C.sub.1-C.sub.6
alkylsulfinyl group, C.sub.1-C.sub.6 alkylsulfonyl group, halo
C.sub.1-C.sub.6 alkylsulfonyl group, phenyl group, substituted
phenyl group having at least one, the same or different
substituents selected from the group consisting of halogen atom,
C.sub.1-C.sub.6 alkyl group, halo C.sub.1-C.sub.6 alkyl group,
C.sub.1-C.sub.6 alkoxy group, halo C.sub.1-C.sub.6 alkoxy group,
C.sub.1-C.sub.6 alkylthio group, halo C.sub.1-C.sub.6 alkylthio
group, C.sub.1-C.sub.6 alkylsulfinyl group, halo C.sub.1-C.sub.6
alkylsulfinyl group, C.sub.1-C.sub.6 alkylsulfonyl group and halo
C.sub.1-C.sub.6 alkylsulfonyl group, heterocyclic group (the term
heterocyclic group is as defined above) and substituted
heterocyclic group (the term heterocyclic group is as defined
above) having at least one, the same or different substituents
selected from the group consisting of halogen atom, C.sub.1-C.sub.6
alkyl group, halo C.sub.1-C.sub.6 alkyl group, C.sub.1-C.sub.6
alkoxy group, halo C.sub.1-C.sub.6 alkoxy group, C.sub.1-C.sub.6
alkylthio group, halo C.sub.1-C.sub.6 alkylthio group,
C.sub.1-C.sub.6 alkylsulfinyl group, halo C.sub.1-C.sub.6
alkylsulfinyl group, C.sub.1-C.sub.6 alkylsulfonyl group and halo
C.sub.1-C.sub.6 alkylsulfonyl group; and Z.sup.1 and Z.sup.2
represent an oxygen atom or a sulfur atom; and one or more
compounds selected from compounds having an insecticidal,
acaricidal or nematocidal activity.
2. A composition for noxious organisms-controlling agent according
to claim 1, wherein R.sup.1 represents a hydrogen atom, R.sup.2
represents a C.sub.1-C.sub.6 alkyl group, a C.sub.1-C.sub.6
alkylthio C.sub.1-C.sub.6 alkyl group, a C.sub.1-C.sub.6
alkylsulfinyl C.sub.1-C.sub.6 alkyl group or a C.sub.1-C.sub.6
alkylsulfonyl C.sub.1-C.sub.6 alkyl group, R.sup.3 represents a
hydrogen atom, X represents a halogen atom, n represents 1, each of
Z.sup.1 and Z.sup.2 represents an oxygen atom, Y may be the same or
different and represents a halogen atom, a C.sub.1-C.sub.6 alkyl
group, a halo C.sub.1-C.sub.6 alkyl group or a halo C.sub.1-C.sub.6
alkoxy group, and m represents 2 or 3.
3. A composition for noxious organisms-controlling agent according
to claim 2, wherein the phthalamide derivative represented by
general formula (I) is
N.sup.2-(1,1-dimethyl-2-methylthioethyl)-3-iodo-N.sup.1-{2-methyl-4-[1,2,-
2,2-tetrafluoro-1-(trifluoromethyl)-ethyl]phenyl}phthalamide,
N.sup.2-(1,1-dimethyl-2-methylsulfonylethyl)-3-iodo-N.sup.1-{2-methyl-4-[-
1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]-phenyl}-phthalamide
or
N.sup.2-(1,1-dimethyl-2-methylsulfinylethyl)-3-iodo-N.sup.1-{2-methyl-4-[-
1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenyl}phthalamide.
4. A composition for noxious organisms-controlling agent according
to claim 1, wherein said one or more compounds having an
insecticidal, acaricidal or nematocidal activity is at least one
compound selected from the group consisting of acetamiprid,
pymetrozine, fenitrothion, carbaryl, methomyl, cartap, cyhalothrin,
ethofenprox, teflubenzuron, flufenoxuron, tebufenozide,
fenpyroximate, pyridaben, BPMC (fenobucarb), malathion,
methidathion, fenthion, diazinon, acephate, oxydeprofos,
vamidothion, ethiophencarb, pirimicarb, permethrin, cypermethrin,
bifenthrin, halfenprox, silafluofen, nitenpyram, chlorfluazuron,
methoxyfenozide, tebufenpyrad, pyrimidifen, dicofol, propargite,
hexythiazox, clofentezine, spinosad, milbemectin, BT (bacillus
thuringiensis), indoxacarb, chlorfenapyr, fipronil, etoxazole,
acequinocyl, pirimiphos-methyl, acrinathrin, quinomethionate,
chlorpyrifos, avermectin, fenbutatin oxide, terbufos, ethoprophos,
cadusafos, fenamiphos, fensulfothion, DSP, dichlofenthion,
fosthiazate, oxamyl, isamidofos, fosthietan, isazofos, thionazin,
benfuracarb and spirodiclofen.
5. A composition for noxious organisms-controlling agent according
to claim 1, wherein the amount of said one or more compounds
selected from compounds having an insecticidal, acaricidal or
nematocidal activity is 0.05 to 2,000 parts by weight per part by
weight of the phthalamide derivative.
6. A method for using a composition for noxious
organisms-controlling agent characterized by treating an objective
noxious organism, an objective useful plant, a seed of an objective
useful plant, soil or a cultivation carrier with an effective
amount of the composition for noxious organisms-controlling agent
according to claim 1 for the purpose of protecting an useful plant
from a noxious organism.
Description
TECHNICAL FIELD
[0001] The present invention relates to a composition for noxious
organisms-controlling agent having a synergistic effect and a
method for using said composition, which comprises a phthalamide
derivative represented by general formula (I) being useful as an
insecticide or acaricide and one or more compounds selected from
the compounds having insecticidal, acaricidal or nematocidal
activity.
BACKGROUND ART
[0002] The phthalamide derivatives of the present invention
represented by general formula (I) are known compounds disclosed in
JP-A-11-240857 and JP-A-2001-131141, wherein it is mentioned that
these compounds have an insecticidal or acaricidal activity.
[0003] On the other hand, the compounds having insecticidal,
acaricidal or nematocidal activity, as the second active ingredient
of the present invention, are known compounds as disclosed in The
Pesticide Manual Eleventh Edition 1997, etc.
DISCLOSURE OF THE INVENTION
[0004] There exist many noxious organisms which are difficult or
impossible to control by the use of a single member selected from
the phthalamide derivatives represented by the general formula (I)
of the present invention and the insecticidal, acaricidal or
nematocidal compounds. Accordingly, it is expected that discovery
of the means and method for the effective control of such noxious
organisms will lead to a more effective production of crop
plants.
[0005] With the aim of solving the problem mentioned above, the
present inventors have conducted extensive studies. As a result, it
has been found that a plurality of noxious organisms can be
controlled effectively by the combined use of one or more compounds
selected from the phthalamide derivatives represented by the
general formula (I) and one or more compounds selected from the
insecticidal, acaricidal or nematocidal compounds. The present
invention has been accomplished on the basis of this finding.
[0006] The present invention relates to a composition for noxious
organisms-controlling agent comprising, as active ingredients
thereof, one or more compounds selected from the phthalamide
derivatives represented by the general formula (I):
##STR00002##
wherein R.sup.1, R.sup.2 and R.sup.3, which may be the same or
different, each represent a hydrogen atom, a C.sub.3-C.sub.6
cycloalkyl group, a halo C.sub.3-C.sub.6 cycloalkyl group or
-A.sup.1-Q.sub.P (in this formula, A.sup.1 represents a
C.sub.1-C.sub.8 alkylene group, a C.sub.3-C.sub.6 alkenylene group
or a C.sub.3-C.sub.6 alkynylene group; Q represents a hydrogen
atom; a halogen atom; a cyano group; a nitro group; a halo
C.sub.1-C.sub.6 alkyl group; a C.sub.3-C.sub.6 cycloalkyl group; a
halo C.sub.3-C.sub.6 cycloalkyl group; a C.sub.1-C.sub.6
alkoxycarbonyl group; a di C.sub.1-C.sub.6 alkoxyphosphoryl group
in which the alkoxy groups may be the same or different; a di
C.sub.1-C.sub.6 alkoxythiophosphoryl group in which the alkoxy
groups may be the same or different; a diphenylphosphino group; a
diphenylphosphono group; a phenyl group; a substituted phenyl group
having at least one, the same or different substituents selected
from the group consisting of halogen atom, C.sub.1-C.sub.6 alkyl
group, halo C.sub.1-C.sub.6 alkyl group, C.sub.1-C.sub.6 alkoxy
group, halo C.sub.1-C.sub.6 alkoxy group, C.sub.1-C.sub.6 alkylthio
group, halo C.sub.1-C.sub.6 alkylthio group, C.sub.1-C.sub.6
alkylsulfinyl group, halo C.sub.1-C.sub.6 alkylsulfinyl group,
C.sub.1-C.sub.6 alkylsulfonyl group and halo C.sub.1-C.sub.6
alkylsulfonyl group; a heterocyclic group (the term heterocyclic
group means a pyridyl group, a pyridine-N-oxide group, a
pyrimidinyl group, a furyl group, a tetrahydrofuryl group, a
thienyl group, a tetrahydrothienyl group, a tetrahydropyranyl
group, a tetrahydrothiopyranyl group, an oxazolyl group, an
isoxazolyl group, an oxadiazolyl group, a thiazolyl group, an
isothiazolyl group, a thiadiazolyl group, an imidazolyl group, a
triazolyl group or a pyrazolyl group); a substituted heterocyclic
group (the term heterocyclic group is as defined above) having at
least one, the same or different substituents selected from the
group consisting of halogen atom, C.sub.1-C.sub.6 alkyl group, halo
C.sub.1-C.sub.6 alkyl group, C.sub.1-C.sub.6 alkoxy group, halo
C.sub.1-C.sub.6 alkoxy group, C.sub.1-C.sub.6 alkylthio group, halo
C.sub.1-C.sub.6 alkylthio group, C.sub.1-C.sub.6 alkylsulfinyl
group, halo C.sub.1-C.sub.6 alkylsulfinyl group, C.sub.1-C.sub.6
alkylsulfonyl group and halo C.sub.1-C.sub.6 alkylsulfonyl group;
or --Z.sup.3--R.sup.4 (in this formula, Z.sup.3 represents --O--,
--S--, --SO--, --SO.sub.2-- or --N(R.sup.5)-- (in this formula,
R.sup.5 represents a hydrogen atom; a C.sub.1-C.sub.6 alkylcarbonyl
group; a halo C.sub.1-C.sub.6 alkylcarbonyl group; a
C.sub.1-C.sub.6 alkoxycarbonyl group; a phenylcarbonyl group; a
substituted phenylcarbonyl group having at least one, the same or
different substituents selected from the group consisting of
halogen atom, C.sub.1-C.sub.6 alkyl group, halo C.sub.1-C.sub.6
alkyl group, C.sub.1-C.sub.6 alkoxy group, halo C.sub.1-C.sub.6
alkoxy group, C.sub.1-C.sub.6 alkylthio group, halo C.sub.1-C.sub.6
alkylthio group, C.sub.1-C.sub.6 alkylsulfinyl group, halo
C.sub.1-C.sub.6 alkylsulfinyl group, C.sub.1-C.sub.6 alkylsulfonyl
group and halo C.sub.1-C.sub.6 alkylsulfonyl group; a phenyl
C.sub.1-C.sub.4 alkoxycarbonyl group; or a substituted phenyl
C.sub.1-C.sub.4 alkoxycarbonyl group having, on the ring thereof,
at least one, the same or different substituents selected from the
group consisting of halogen atom, C.sub.1-C.sub.6 alkyl group, halo
C.sub.1-C.sub.6 alkyl group, C.sub.1-C.sub.6 alkoxy group, halo
C.sub.1-C.sub.6 alkoxy group, C.sub.1-C.sub.6 alkylthio group, halo
C.sub.1-C.sub.6 alkylthio group, C.sub.1-C.sub.6 alkylsulfinyl
group, halo C.sub.1-C.sub.6 alkylsulfinyl group, C.sub.1-C.sub.6
alkylsulfonyl group and halo C.sub.1-C.sub.6 alkylsulfonyl group),
and R.sup.4 represents a hydrogen atom; a C.sub.1-C.sub.6 alkyl
group; a halo C.sub.1-C.sub.6 alkyl group; a C.sub.3-C.sub.6
alkenyl group; a halo C.sub.3-C.sub.6 alkenyl group; a
C.sub.3-C.sub.6 alkynyl group; a halo C.sub.3-C.sub.6 alkynyl
group; a C.sub.3-C.sub.6 cycloalkyl group; a halo C.sub.3-C.sub.6
cycloalkyl group; a C.sub.1-C.sub.6 alkylcarbonyl group; a halo
C.sub.1-C.sub.6 alkylcarbonyl group; a C.sub.1-C.sub.6
alkoxycarbonyl group; a phenyl group; a substituted phenyl group
having at least one, the same or different substituents selected
from the group consisting of halogen atom, C.sub.1-C.sub.6 alkyl
group, halo C.sub.1-C.sub.6 alkyl group, C.sub.1-C.sub.6 alkoxy
group, halo C.sub.1-C.sub.6 alkoxy group, C.sub.1-C.sub.6 alkylthio
group, halo C.sub.1-C.sub.6 alkylthio group, C.sub.1-C.sub.6
alkylsulfinyl group, halo C.sub.1-C.sub.6 alkylsulfinyl group,
C.sub.1-C.sub.6 alkylsulfonyl group and halo C.sub.1-C.sub.6
alkylsulfonyl group; a phenyl C.sub.1-C.sub.4 alkyl group; a
substituted phenyl C.sub.1-C.sub.4 alkyl group having, on the ring
thereof, at least one, the same or different substituents selected
from the group consisting of halogen atom, C.sub.1-C.sub.6 alkyl
group, halo C.sub.1-C.sub.6 alkyl group, C.sub.1-C.sub.6 alkoxy
group, halo C.sub.1-C.sub.6 alkoxy group, C.sub.1-C.sub.6 alkylthio
group, halo C.sub.1-C.sub.6 alkylthio group, C.sub.1-C.sub.6
alkylsulfinyl group, halo C.sub.1-C.sub.6 alkylsulfinyl group,
C.sub.1-C.sub.6 alkylsulfonyl group and halo C.sub.1-C.sub.6
alkylsulfonyl group; a heterocyclic group (the term heterocyclic
group is as defined above); or a substituted heterocyclic group
(the term heterocyclic group is as defined above) having at least
one, the same or different substituents selected from the group
consisting of halogen atom, C.sub.1-C.sub.6 alkyl group, halo
C.sub.1-C.sub.6 alkyl group, C.sub.1-C.sub.6 alkoxy group, halo
C.sub.1-C.sub.6 alkoxy group, C.sub.1-C.sub.6 alkylthio group, halo
C.sub.1-C.sub.6 alkylthio group, C.sub.1-C.sub.6 alkylsulfinyl
group, halo C.sub.1-C.sub.6 alkylsulfinyl group, C.sub.1-C.sub.6
alkylsulfonyl group and halo C.sub.1-C.sub.6 alkylsulfonyl group);
and p represents an integer of 1-4); and R.sup.1 and R.sup.2 may be
taken conjointly to form a 4- to 7-membered ring which may be
interrupted by one to three, the same or different hetero atoms
selected from oxygen atom, sulfur atom and nitrogen atom;
[0007] X may be the same or different and represents a hydrogen
atom; a halogen atom; a cyano group; a nitro group; a
C.sub.3-C.sub.6 cycloalkyl group; a halo C.sub.3-C.sub.6 cycloalkyl
group; a phenyl group; a substituted phenyl group having at least
one, the same or different substituents selected from the group
consisting of halogen atom, C.sub.1-C.sub.6 alkyl group, halo
C.sub.1-C.sub.6 alkyl group, C.sub.1-C.sub.6 alkoxy group, halo
C.sub.1-C.sub.6 alkoxy group, C.sub.1-C.sub.6 alkylthio group, halo
C.sub.1-C.sub.6 alkylsulfinyl group, C.sub.1-C.sub.6 alkylsulfinyl
group, halo C.sub.1-C.sub.6 alkylsulfinyl group, C.sub.1-C.sub.6
alkylsulfonyl group and halo C.sub.1-C.sub.6 alkylsulfonyl group; a
heterocyclic group (the term heterocyclic group is as defined
above); a substituted heterocyclic group (the term heterocyclic
group is as defined above) having at least one, the same or
different substituents selected from the group consisting of
halogen atom, C.sub.1-C.sub.6 alkyl group, halo C.sub.1-C.sub.6
alkyl group, C.sub.1-C.sub.6 alkoxy group, halo C.sub.1-C.sub.6
alkoxy group, C.sub.1-C.sub.6 alkylthio group, halo C.sub.1-C.sub.6
alkylthio group, C.sub.1-C.sub.6 alkylsulfinyl group, halo
C.sub.1-C.sub.6 alkylsulfinyl group, C.sub.1-C.sub.6 alkylsulfonyl
group and halo C.sub.1-C.sub.6 alkylsulfonyl group; or
-A.sup.2-R.sup.6 (in this formula, A.sup.2 represents --O--, --S--,
--SO--, --SO.sub.2--, --C(.dbd.O)--, --C(.dbd.NOR.sup.7)-- (in this
formula, R.sup.7 represents a hydrogen atom, a C.sub.1-C.sub.6
alkyl group, a halo C.sub.1-C.sub.6 alkyl group, a C.sub.3-C.sub.6
alkenyl group, a halo C.sub.3-C.sub.6 alkenyl group, a
C.sub.3-C.sub.6 alkynyl group, a cyclo C.sub.3-C.sub.6 alkyl group,
a phenyl C.sub.1-C.sub.4 alkyl group or a substituted phenyl
C.sub.1-C.sub.4 alkyl group having, on the ring thereof, at least
one, the same or different substituents selected from the group
consisting of halogen atom, C.sub.1-C.sub.6 alkyl group, halo
C.sub.1-C.sub.6 alkyl group, C.sub.1-C.sub.6 alkoxy group, halo
C.sub.1-C.sub.6 alkoxy group, C.sub.1-C.sub.6 alkylthio group, halo
C.sub.1-C.sub.6 alkylthio group, C.sub.1-C.sub.6 alkylsulfinyl
group, halo C.sub.1-C.sub.6 alkylsulfinyl group, C.sub.1-C.sub.6
alkylsulfonyl group and halo C.sub.1-C.sub.6 alkylsulfonyl group),
a C.sub.1-C.sub.6 alkylene group, a halo C.sub.1-C.sub.6 alkylene
group, a C.sub.2-C.sub.6 alkenylene group, a halo C.sub.2-C.sub.6
alkenylene group, a C.sub.2-C.sub.6 alkynylene group or a halo
C.sub.3-C.sub.6 alkynylene group, and
(1) in a case where A.sup.2 represents --O--, --S--, --SO-- or
--SO.sub.2--, R.sup.6 represents a halo C.sub.3-C.sub.6 cycloalkyl
group; a halo C.sub.3-C.sub.6 cycloalkenyl group; a phenyl group; a
substituted phenyl group having at least one, the same or different
substituents selected from the group consisting of halogen atom,
C.sub.1-C.sub.6 alkyl group, halo C.sub.1-C.sub.6 alkyl group,
C.sub.1-C.sub.6 alkoxy group, halo C.sub.1-C.sub.6 alkoxy group,
C.sub.1-C.sub.6 alkylthio group, halo C.sub.1-C.sub.6 alkylthio
group, C.sub.1-C.sub.6 alkylsulfinyl group, halo C.sub.1-C.sub.6
alkylsulfinyl group, C.sub.1-C.sub.6 alkylsulfonyl group and halo
C.sub.1-C.sub.6 alkylsulfonyl group; a heterocyclic group (the term
heterocyclic group is as defined above); a substituted heterocyclic
group (the term heterocyclic group is as defined above) having at
least one, the same or different substituents selected from the
group consisting of halogen atom, C.sub.1-C.sub.6 alkyl group, halo
C.sub.1-C.sub.6 alkyl group, C.sub.1-C.sub.6 alkoxy group, halo
C.sub.1-C.sub.6 alkoxy group, C.sub.1-C.sub.6 alkylthio group, halo
C.sub.1-C.sub.6 alkylthio group, C.sub.1-C.sub.6 alkylsulfinyl
group, halo C.sub.1-C.sub.6 alkylsulfinyl group, C.sub.1-C.sub.6
alkylsulfonyl group and halo C.sub.1-C.sub.6 alkylsulfonyl group;
or -A.sup.3-R.sup.8 (in this formula, A.sup.3 represents a
C.sub.1-C.sub.6 alkylene group, a halo C.sub.1-C.sub.6 alkylene
group, a C.sub.3-C.sub.6 alkenylene group, a halo C.sub.3-C.sub.6
alkenylene group, a C.sub.3-C.sub.6 alkynylene group or a halo
C.sub.3-C.sub.6 alkynylene group, and R.sup.8 represents a hydrogen
atom; a halogen atom; a C.sub.3-C.sub.6 cycloalkyl group; a halo
C.sub.3-C.sub.6 cycloalkyl group; a C.sub.1-C.sub.6 alkoxycarbonyl
group; a phenyl group; a substituted phenyl group having at least
one, the same or different substituents selected from the group
consisting of halogen atom, C.sub.1-C.sub.6 alkyl group, halo
C.sub.1-C.sub.6 alkyl group, C.sub.1-C.sub.6 alkoxy group, halo
C.sub.1-C.sub.6 alkoxy group, C.sub.1-C.sub.6 alkylthio group, halo
C.sub.1-C.sub.6 alkylthio group, C.sub.1-C.sub.6 alkylsulfinyl
group, halo C.sub.1-C.sub.6 alkylsulfinyl group, C.sub.1-C.sub.6
alkylsulfonyl group and halo C.sub.1-C.sub.6 alkylsulfonyl group;
or -A.sup.4-R.sup.9 (in this formula, A.sup.4 represents --O--,
--S--, --SO--, --SO.sub.2-- or --C(.dbd.O), and R.sup.9 represents
a C.sub.1-C.sub.6 alkyl group; a halo C.sub.1-C.sub.6 alkyl group;
a C.sub.3-C.sub.6 alkenyl group; a halo C.sub.3-C.sub.6 alkenyl
group; a C.sub.3-C.sub.6 cycloalkyl group; a halo C.sub.3-C.sub.6
cycloalkyl group; a phenyl group; a substituted phenyl group having
at least one, the same or different substituents selected from the
group consisting of halogen atom, C.sub.1-C.sub.6 alkyl group, halo
C.sub.1-C.sub.6 alkyl group, C.sub.1-C.sub.6 alkoxy group, halo
C.sub.1-C.sub.6 alkoxy group, C.sub.1-C.sub.6 alkylthio group, halo
C.sub.1-C.sub.6 alkylthio group, C.sub.1-C.sub.6 alkylsulfinyl
group, halo C.sub.1-C.sub.6 alkylsulfinyl group, C.sub.1-C.sub.6
alkylsulfonyl group and halo C.sub.1-C.sub.6 alkylsulfonyl group; a
heterocyclic group (the term heterocyclic group is as defined
above); or a substituted heterocyclic group (the term heterocyclic
group is as defined above) having at least one, the same or
different substituents selected from the group consisting of
halogen atom, C.sub.1-C.sub.6 alkyl group, halo C.sub.1-C.sub.6
alkyl group, C.sub.1-C.sub.6 alkoxy group, halo C.sub.1-C.sub.6
alkoxy group, C.sub.1-C.sub.6 alkylthio group, halo C.sub.1-C.sub.6
alkylthio group, C.sub.1-C.sub.6 alkylsulfinyl group, halo
C.sub.1-C.sub.6 alkylsulfinyl group, C.sub.1-C.sub.6 alkylsulfonyl
group and halo C.sub.1-C.sub.6 alkylsulfonyl group)), (2) in a case
where A.sup.2 represents --C(.dbd.O)-- or --C(.dbd.NOR.sup.7)-- (in
this formula, R.sup.7 is as defined above), Rrepresents a
C.sub.1-C.sub.6 alkyl group; a halo C.sub.1-C.sub.6 alkyl group; a
C.sub.2-C.sub.6 alkenyl group; a halo C.sub.2-C.sub.6 alkenyl
group; a C.sub.3-C.sub.6 cycloalkyl group; a halo C.sub.3-C.sub.6
cycloalkyl group; a C.sub.1-C.sub.6 alkoxy group; a C.sub.1-C.sub.6
alkylthio group; a mono C.sub.1-C.sub.6 alkylamino group; a di
C.sub.1-C.sub.6 alkylamino group in which the alkyl groups may be
the same or different; a phenyl group; a substituted phenyl group
having at least one, the same or different substituents selected
from the group consisting of halogen atom, C.sub.1-C.sub.6 alkyl
group, halo C.sub.1-C.sub.6 alkyl group, C.sub.1-C.sub.6 alkoxy
group, halo C.sub.1-C.sub.6 alkoxy group, C.sub.1-C.sub.6 alkylthio
group, halo C.sub.1-C.sub.6 alkylthio group, C.sub.1-C.sub.6
alkylsulfinyl group, halo C.sub.1-C.sub.6 alkylsulfinyl group,
C.sub.1-C.sub.6 alkylsulfonyl group and halo C.sub.1-C.sub.6
alkylsulfonyl group; a phenylamino group; a substituted phenylamino
group having, on the ring thereof, at least one, the same or
different substituents selected from the group consisting of
halogen atom, C.sub.1-C.sub.6 alkyl group, halo C.sub.1-C.sub.6
alkyl group, C.sub.1-C.sub.6 alkoxy group, halo C.sub.1-C.sub.6
alkoxy group, C.sub.1-C.sub.6 alkylthio group, halo C.sub.1-C.sub.6
alkylthio group, C.sub.1-C.sub.6 alkylsulfinyl group, halo
C.sub.1-C.sub.6 alkylsulfinyl group, C.sub.1-C.sub.6 alkylsulfonyl
group and halo C.sub.1-C.sub.6 alkylsulfonyl group; a heterocyclic
group (the term heterocyclic group is as defined above); or a
substituted heterocyclic group (the term heterocyclic group is as
defined above) having at least one, the same or different
substituents selected from the group consisting of halogen atom,
C.sub.1-C.sub.6 alkyl group, halo C.sub.1-C.sub.6 alkyl group,
C.sub.1-C.sub.6 alkoxy group, halo C.sub.1-C.sub.6 alkoxy group,
C.sub.1-C.sub.6 alkylthio group, halo C.sub.1-C.sub.6 alkylthio
group, C.sub.1-C.sub.6 alkylsulfinyl group, halo C.sub.1-C.sub.6
alkylsulfinyl group, C.sub.1-C.sub.6 alkylsulfonyl group and halo
C.sub.1-C.sub.6 alkylsulfonyl group, and (3) in a case where
A.sup.2 represents a C.sub.1-C.sub.6 alkylene group, a halo
C.sub.1-C.sub.6 alkylene group, a C.sub.2-C.sub.6 alkenylene group,
a halo C.sub.2-C.sub.6 alkenylene group, a C.sub.2-C.sub.6
alkynylene group or a halo C.sub.3-C.sub.6 alkynylene group,
R.sup.6 represents a hydrogen atom; a halogen atom; a
C.sub.3-C.sub.6 cycloalkyl group; a halo C.sub.3-C.sub.6 cycloalkyl
group; a C.sub.1-C.sub.6 alkoxycarbonyl group; a phenyl group; a
substituted phenyl group having at least one, the same or different
substituents selected from the group consisting of halogen atom,
C.sub.1-C.sub.6 alkyl group, halo C.sub.1-C.sub.6 alkyl group,
C.sub.1-C.sub.6 alkoxy group, halo C.sub.1-C.sub.6 alkoxy group,
C.sub.1-C.sub.6 alkylthio group, halo C.sub.1-C.sub.6 alkylthio
group, C.sub.1-C.sub.6 alkylsulfinyl group, halo C.sub.1-C.sub.6
alkylsulfinyl group, C.sub.1-C.sub.6 alkylsulfonyl group and halo
C.sub.1-C.sub.6 alkylsulfonyl group; a heterocyclic group (the term
heterocyclic group is as defined above); a substituted heterocyclic
group (the term heterocyclic group is as defined above) having at
least one, the same or different substituents selected from the
group consisting of halogen atom, C.sub.1-C.sub.6 alkyl group, halo
C.sub.1-C.sub.6 alkyl group, C.sub.1-C.sub.6 alkoxy group, halo
C.sub.1-C.sub.6 alkoxy group, C.sub.1-C.sub.6 alkylthio group, halo
C.sub.1-C.sub.6 alkylthio group, C.sub.1-C.sub.6 alkylsulfinyl
group, halo C.sub.1-C.sub.6 alkylsulfinyl group, C.sub.1-C.sub.6
alkylsulfonyl group and halo C.sub.1-C.sub.6 alkylsulfonyl group;
or -A.sup.5-R.sup.10 (in this formula, A.sup.5 represents --O--,
--S--, --SO-- or --SO.sub.2--, and R.sup.10 represents a
C.sub.3-C.sub.6 cycloalkyl group; a halo C.sub.3-C.sub.6 cycloalkyl
group; a phenyl group; a substituted phenyl group having at least
one, the same or different substituents selected from the group
consisting of halogen atom, C.sub.1-C.sub.6 alkyl group, halo
C.sub.1-C.sub.6 alkyl group, C.sub.1-C.sub.6 alkoxy group, halo
C.sub.1-C.sub.6 alkoxy group, C.sub.1-C.sub.6 alkylthio group, halo
C.sub.1-C.sub.6 alkylthio group, C.sub.1-C.sub.6 alkylsulfinyl
group, halo C.sub.1-C.sub.6 alkylsulfinyl group, C.sub.1-C.sub.6
alkylsulfonyl group and halo C.sub.1-C.sub.6 alkylsulfonyl group; a
heterocyclic group (the term heterocyclic group is as defined
above); a substituted heterocyclic group (the term heterocyclic
group is as defined above) having at least one, the same or
different substituents selected from the group consisting of
halogen atom, C.sub.1-C.sub.6 alkyl group, halo C.sub.1-C.sub.6
alkyl group, C.sub.1-C.sub.6 alkoxy group, halo C.sub.1-C.sub.6
alkoxy group, C.sub.1-C.sub.6 alkylthio group, halo C.sub.1-C.sub.6
alkylthio group, C.sub.1-C.sub.6 alkylsulfinyl group, halo
C.sub.1-C.sub.6 alkylsulfinyl group, C.sub.1-C.sub.6 alkylsulfonyl
group and halo C.sub.1-C.sub.6 alkylsulfonyl group; or
-A.sup.6-R.sup.11 (in this formula, A.sup.6 represents a
C.sub.1-C.sub.6 alkylene group; a halo C.sub.1-C.sub.6 alkylene
group; a C.sub.2-C.sub.6 alkenylene group; a halo C.sub.2-C.sub.6
alkenylene group; a C.sub.2-C.sub.6 alkynylene group; or a halo
C.sub.3-C.sub.6 alkynylene group; and R.sup.11 represents a
hydrogen atom; a halogen atom; a C.sub.3-C.sub.6 cycloalkyl group;
a halo C.sub.3-C.sub.6 cycloalkyl group; a C.sub.1-C.sub.6 alkoxy
group; a halo C.sub.1-C.sub.6 alkoxy group; a C.sub.1-C.sub.6
alkylthio group; a halo C.sub.1-C.sub.6 alkylthio group; a
C.sub.1-C.sub.6 alkylsulfinyl group; a halo C.sub.1-C.sub.6
alkylsulfinyl group; a C.sub.1-C.sub.6 alkylsulfonyl group; a halo
C.sub.1-C.sub.6 alkylsulfonyl group; a phenyl group; a substituted
phenyl group having at least one, the same or different
substituents selected from the group consisting of halogen atom,
C.sub.1-C.sub.6 alkyl group, halo C.sub.1-C.sub.6 alkyl group,
C.sub.1-C.sub.6 alkoxy group, halo C.sub.1-C.sub.6 alkoxy group,
C.sub.1-C.sub.6 alkylthio group, halo C.sub.1-C.sub.6 alkylthio
group, C.sub.1-C.sub.6 alkylsulfinyl group, halo C.sub.1-C.sub.6
alkylsulfinyl group, C.sub.1-C.sub.6 alkylsulfonyl group and halo
C.sub.1-C.sub.6 alkylsulfonyl group; a phenoxy group; a substituted
phenoxy group having at least one, the same or different
substituents selected from the group consisting of halogen atom,
C.sub.1-C.sub.6 alkyl group, halo C.sub.1-C.sub.6 alkyl group,
C.sub.1-C.sub.6 alkoxy group, halo C.sub.1-C.sub.6 alkoxy group,
C.sub.1-C.sub.6 alkylthio group, halo C.sub.1-C.sub.6 alkylthio
group, C.sub.1-C.sub.6 alkylsulfinyl group, halo C.sub.1-C.sub.6
alkylsulfinyl group, C.sub.1-C.sub.6 alkylsulfonyl group and halo
C.sub.1-C.sub.6 alkylsulfonyl group; a phenylthio group; a
substituted phenylthio group having at least one, the same or
different substituents selected from the group consisting of
halogen atom, C.sub.1-C.sub.6 alkyl group, halo C.sub.1-C.sub.6
alkyl group, C.sub.1-C.sub.6 alkoxy group, halo C.sub.1-C.sub.6
alkoxy group, C.sub.1-C.sub.6 alkylthio group, halo C.sub.1-C.sub.6
alkylthio group, C.sub.1-C.sub.6 alkylsulfinyl group, halo
C.sub.1-C.sub.6 alkylsulfinyl group, C.sub.1-C.sub.6 alkylsulfonyl
group and halo C.sub.1-C.sub.6 alkylsulfonyl group; a heterocyclic
group (the term heterocyclic group is as defined above; or a
substituted heterocyclic group (the term heterocyclic group is as
defined above) having at least one, the same or different
substituents selected from the group consisting of halogen atom,
C.sub.1-C.sub.6 alkyl group, halo C.sub.1-C.sub.6 alkyl group,
C.sub.1-C.sub.6 alkoxy group, halo C.sub.1-C.sub.6 alkoxy group,
C.sub.1-C.sub.6 alkylthio group, halo C.sub.1-C.sub.6 alkylthio
group, C.sub.1-C.sub.6 alkylsulfinyl group, halo C.sub.1-C.sub.6
alkylsulfinyl group, C.sub.1-C.sub.6 alkylsulfonyl group and halo
C.sub.1-C.sub.6 alkylsulfonyl group))), and
[0008] n represents an integer of 1-4;
and X may be taken conjointly together with an adjacent carbon atom
on the phenyl ring to form a condensed ring (the term condensed
ring means naphthalene, tetrahydronaphthalene, indene, indane,
quinoline, quinazoline, chromane, isochromane, indole, indoline,
benzodioxane, benzodioxole, benzofuran, dihydrobenzofuran,
benzothiophene, dihydrobenzothiophene, benzoxazole, benzothiazole,
benzimidazole or indazole), and said condensed ring may have at
least one, the same or different substituents selected from the
group consisting of halogen atom, C.sub.1-C.sub.6 alkyl group, halo
C.sub.1-C.sub.6 alkyl group, C.sub.1-C.sub.6 alkoxy group, halo
C.sub.1-C.sub.6 alkoxy group, C.sub.1-C.sub.6 alkylthio group, halo
C.sub.1-C.sub.6 alkylthio group, C.sub.1-C.sub.6 alkylsulfinyl
group, halo C.sub.1-C.sub.6 alkylsulfinyl group, C.sub.1-C.sub.6
alkylsulfonyl group, halo C.sub.1-C.sub.6 alkylsulfonyl group,
phenyl group, substituted phenyl group having at least one, the
same or different substituents selected from the group consisting
of halogen atom, C.sub.1-C.sub.6 alkyl group, halo C.sub.1-C.sub.6
alkyl group, C.sub.1-C.sub.6 alkoxy group, halo C.sub.1-C.sub.6
alkoxy group, C.sub.1-C.sub.6 alkylthio group, halo C.sub.1-C.sub.6
alkylthio group, C.sub.1-C.sub.6 alkylsulfinyl group, halo
C.sub.1-C.sub.6 alkylsulfinyl group, C.sub.1-C.sub.6 alkylsulfonyl
group and halo C.sub.1-C.sub.6 alkylsulfonyl group, heterocyclic
group (the term heterocyclic group is as defined above) and
substituted heterocyclic group (the term heterocyclic group is as
defined above) having at least one, the same or different
substituents selected from the group consisting of halogen atom,
C.sub.1-C.sub.6 alkyl group, halo C.sub.1-C.sub.6 alkyl group,
C.sub.1-C.sub.6 alkoxy group, halo C.sub.1-C.sub.6 alkoxy group,
C.sub.1-C.sub.6 alkylthio group, halo C.sub.1-C.sub.6 alkylthio
group, C.sub.1-C.sub.6 alkylsulfinyl group, halo C.sub.1-C.sub.6
alkylsulfinyl group, C.sub.1-C.sub.6 alkylsulfonyl group and halo
C.sub.1-C.sub.6 alkylsulfonyl group; and
[0009] Y may be the same or different and represents a hydrogen
atom; a halogen atom; a cyano group; a nitro group; a halo
C.sub.3-C.sub.6 cycloalkyl group; a phenyl group; a substituted
phenyl group having at least one, the same or different
substituents selected from the group consisting of halogen atom,
C.sub.1-C.sub.6 alkyl group, halo C.sub.1-C.sub.6 alkyl group,
C.sub.1-C.sub.6 alkoxy group, halo C.sub.1-C.sub.6 alkoxy group,
C.sub.1-C.sub.6 alkylthio group, halo C.sub.1-C.sub.6 alkylthio
group, C.sub.1-C.sub.6 alkylsulfinyl group, halo C.sub.1-C.sub.6
alkylsulfinyl group, C.sub.1-C.sub.6 alkylsulfonyl group and halo
C.sub.1-C.sub.6 alkylsulfonyl group; a heterocyclic group (the term
heterocyclic group is as defined above); a substituted heterocyclic
group (the term heterocyclic group is as defined above) having at
least one, the same or different substituents selected from the
group consisting of halogen atom, C.sub.1-C.sub.6 alkyl group, halo
C.sub.1-C.sub.6 alkyl group, C.sub.1-C.sub.6 alkoxy group, halo
C.sub.1-C.sub.6 alkoxy group, C.sub.1-C.sub.6 alkylthio group, halo
C.sub.1-C.sub.6 alkylthio group, C.sub.1-C.sub.6 alkylsulfinyl
group, halo C.sub.1-C.sub.6 alkylsulfinyl group, C.sub.1-C.sub.6
alkylsulfonyl group and halo C.sub.1-C.sub.6 alkylsulfonyl group;
or -A.sup.2-R.sup.6 (in this formula, A.sup.2 and R.sup.6 are as
defined above); and m represents an integer of 1-5; and
[0010] Y may be taken conjointly together with an adjacent carbon
atom on the phenyl ring to form a condensed ring (the term
condensed ring is as defined above), and said condensed ring may
have at least one, the same or different substituents selected from
the group consisting of halogen atom, C.sub.1-C.sub.6 alkyl group,
halo C.sub.1-C.sub.6 alkyl group, C.sub.1-C.sub.6 alkoxy group,
halo C.sub.1-C.sub.6 alkoxy group, C.sub.1-C.sub.6 alkylthio group,
halo C.sub.1-C.sub.6 alkylthio group, C.sub.1-C.sub.6 alkylsulfinyl
group, halo C.sub.1-C.sub.6 alkylsulfinyl group, C.sub.1-C.sub.6
alkylsulfonyl group, halo C.sub.1-C.sub.6 alkylsulfonyl group,
phenyl group, substituted phenyl group having at least one, the
same or different substituents selected from the group consisting
of halogen atom, C.sub.1-C.sub.6 alkyl group, halo C.sub.1-C.sub.6
alkyl group, C.sub.1-C.sub.6 alkoxy group, halo C.sub.1-C.sub.6
alkoxy group, C.sub.1-C.sub.6 alkylthio group, halo C.sub.1-C.sub.6
alkylthio group, C.sub.1-C.sub.6 alkylsulfinyl group, halo
C.sub.1-C.sub.6 alkylsulfinyl group, C.sub.1-C.sub.6 alkylsulfonyl
group and halo C.sub.1-C.sub.6 alkylsulfonyl group, heterocyclic
group (the term heterocyclic group is as defined above) and
substituted heterocyclic group (the term heterocyclic group is as
defined above) having at least one, the same or different
substituents selected from the group consisting of halogen atom,
C.sub.1-C.sub.6 alkyl group, halo C.sub.1-C.sub.6 alkyl group,
C.sub.1-C.sub.6 alkoxy group, halo C.sub.1-C.sub.6 alkoxy group,
C.sub.1-C.sub.6 alkylthio group, halo C.sub.1-C.sub.6 alkylthio
group, C.sub.1-C.sub.6 alkylsulfinyl group, halo C.sub.1-C.sub.6
alkylsulfinyl group, C.sub.1-C.sub.6 alkylsulfonyl group and halo
C.sub.1-C.sub.6 alkylsulfonyl group; and
[0011] Z.sup.1 and Z.sup.2 represent an oxygen atom or a sulfur
atom; and
[0012] one or more compounds selected from compounds having an
insecticidal, acaricidal or nematocidal activity;
[0013] and to a method for using said composition.
[0014] The noxious organisms-controlling agent of the present
invention exhibits a marked effect even when dosage thereof is so
low that any of the ingredients constituting said agent can exhibit
no effect at such a low dosage if used singly, and exhibits a
marked controlling effect against noxious organisms and
agent-resistant noxious organisms which cannot be controlled with
any of the single ingredients.
MODE FOR PRACTICE OF THE INVENTION
[0015] In the definition of general formula (I) representing the
phthalamide derivative of this invention, the term "halogen atom"
means chlorine atom, bromine atom, iodine atom or fluorine atom;
"C.sub.1-C.sub.6 alkyl" means a straight or branched chain alkyl
group having 1-6 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; "halo C.sub.1-C.sub.6 alkyl" means a straight or branched
chain alkyl group having 1-6 carbon atoms which is substituted with
at least one, the same or different halogen atoms; "C.sub.1-C.sub.6
alkylene" means a straight or branched chain alkylene group having
1-8 carbon atoms such as methylene, ethylene, propylene,
trimethylene, dimethylmethylene, tetramethylene, isobutylene,
dimethylethylene, octamethylene and the like;
[0016] As the "4- to 7-membered ring which may be interrupted by 1
to 3, the same or different hetero atoms selected from oxygen atom,
sulfur atom and nitrogen atom" formed through a mutual combination
of R.sup.1 and R.sup.2, for example, azetidine ring, pyrrolidine
ring, pyrroline ring, piperidine ring, imidazolidine ring,
imidazoline ring, oxazolidine ring, thiazolidine ring,
isoxazolidine ring, isothiazolidine ring, tetrahydropyridine ring,
piperazine ring, morpholine ring, thiomorpholine ring, dioxazine
ring, dithiazine ring and the like can be referred to.
[0017] In some cases, the phthalamide derivative of the present
invention represented by general formula (I) may have an asymmetric
carbon atom or an asymmetric center in the structural formula
thereof, and may have two or more optical isomers. The present
invention involves all such optical isomers and mixtures consisting
of the optical isomers at arbitrary ratios. In some cases, the
present invention involves salts, hydrates and the like of these
compounds.
[0018] The phthalamide derivatives represented by general formula
(I) can be obtained by using the compounds and production processes
disclosed in JP-A-11-240857 and JP-A-2001-131141.
[0019] Among the compounds represented by general formula (I),
preferable are those in which R.sup.1 represents a hydrogen atom,
R.sup.2 represents a C.sub.1-C.sub.6 alkyl group, a C.sub.1-C.sub.6
alkylthio C.sub.1-C.sub.6 alkyl group, a C.sub.1-C.sub.6
alkylsulfinyl C.sub.1-C.sub.6 alkyl group or a C.sub.1-C.sub.6
alkylsulfonyl C.sub.1-C.sub.6 alkyl group, R.sup.3 represents a
hydrogen atom, X represents a halogen atom, n represents 1, Z.sup.1
and Z.sup.2 represent an oxygen atom, Y which may be the same or
different represents a halogen atom, a C.sub.1-C.sub.6 alkyl group,
a halo C.sub.1-C.sub.6 alkyl group or a halo C.sub.1-C.sub.6 alkoxy
group, and m represents 2 or 3. Among these compounds, particularly
preferable are the following compounds:
N.sup.2-(1,1-dimethyl-2-methylthioethyl)-3-iodo-N.sup.1-{2-methyl-4-[1,2,-
2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenyl}-phthalamide,
N.sup.2-(1,1-dimethyl-2-methylsulfonylethyl)-3-iodo-N.sup.1-{2-methyl-4-[-
1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]-phenyl}phthalamide
and
N.sup.2-(1,1-dimethyl-2-methylsulfinylethyl)-3-iodo-N.sup.1-{2-methyl-4-[-
1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]-phenyl}phthalamide.
[0020] In Table 1, typical compounds of the present invention are
listed. This invention, however, is by no means limited by these
compounds. As examples of such compounds, the compounds disclosed
in JP-A-11-240857 and JP-A-2001-131141 can be referred to.
##STR00003##
TABLE-US-00001 TABLE 1 (Z.sup.1.dbd.Z.sup.2.dbd.O) Property No
R.sup.1 R.sup.2 R.sup.3 Xn Ym mp .degree. C. 1 CH.sub.3 H H
3-NO.sub.2 2-CH.sub.3-5-Cl 169-171 2 C.sub.2H.sub.5 H H 3-Cl
2-CH.sub.3-4-OCHF.sub.2 179-180 3 C.sub.2H.sub.5 H H 3-NO.sub.2
2-CH.sub.3-5-Cl 175-177 4 n-C.sub.3H.sub.7 H H 3-NO.sub.2
2-CH.sub.3-4-OCHF.sub.2 184-186 5 i-C.sub.3H.sub.7 H H 3-Cl
4-C.sub.4H.sub.9-n 169-171 6 i-C.sub.3H.sub.7 H H 3-Cl
4-C.sub.4H.sub.9-t 224-226 7 i-C.sub.3H.sub.7 H H 3-Cl
4-CF(CF.sub.3).sub.2 198-200 8 i-C.sub.3H.sub.7 H H 3-Cl
4-CF.sub.2CF.sub.2CF.sub.3 203-204 9 i-C.sub.3H.sub.7 H H 3-Cl
4-(CF.sub.2).sub.3CF.sub.3 176-178 10 i-C.sub.3H.sub.7 H H 3-Cl
4-OCF.sub.2CHFOC.sub.3F.sub.7-n 169-171 11 i-C.sub.3H.sub.7 H H
6-Cl 4-SCH.sub.3 193-195 12 i-C.sub.3H.sub.7 H H 3-Cl
4-SO.sub.2CH.sub.3 208-210 13 i-C.sub.3H.sub.7 H H 3-Cl
4-SCHF.sub.2 220-222 14 i-C.sub.3H.sub.7 H H 3-Cl
4-SCF.sub.2CHF.sub.2 198-200 15 i-C.sub.3H.sub.7 H H 3-Cl
4-SO.sub.2CF.sub.2CHF.sub.2 227-230 16 i-C.sub.3H.sub.7 H H 3-Cl
4-COCH.sub.3 217-219 17 i-C.sub.3H.sub.7 H H 3-Cl 4-Ph 215-217 18
i-C.sub.3H.sub.7 H H 3-Cl 2-CH.sub.3-4-OCH.sub.3 191-192 19
i-C.sub.3H.sub.7 H H 3-Cl 2-CH.sub.3-4-CF.sub.2CF.sub.3 199-200 20
i-C.sub.3H.sub.7 H H 3-Cl 2-CH.sub.3-4-OCF.sub.3 199-201 21
i-C.sub.3H.sub.7 H H 3,6-Cl.sub.2 2-CH.sub.3-4-OCHF.sub.2 221-222
22 i-C.sub.3H.sub.7 H H 3-Br 4-OCF.sub.3 208-210 23
i-C.sub.3H.sub.7 H H 3-Br 2-CH.sub.3-4-CF.sub.2CF.sub.3 201-202 24
i-C.sub.3H.sub.7 H H 3-Br 2-CH.sub.3-4-CF(CF.sub.3).sub.2 222-224
25 i-C.sub.3H.sub.7 H H 3-Br 2-CH.sub.3-4-SCH.sub.3 215-217 26
i-C.sub.3H.sub.7 H H 3-Br 2-CH.sub.3-4-(3-CF.sub.3-- 156-158 PhO)
27 i-C.sub.3H.sub.7 H H 3-Br 2-CH.sub.3-4-(5-CF.sub.3- 182-184
2-Pyi-O) 28 i-C.sub.3H.sub.7 H H 3-Br -3-OCH.sub.2O-4- 195-198 29
i-C.sub.3H.sub.7 H H 6-Br 2-CH.sub.3-4-OCF.sub.2CHFCF.sub.3 212-213
30 i-C.sub.3H.sub.7 H H 6-Br 2-CH.sub.3-4-OCF.sub.2CHClF 211-213 31
i-C.sub.3H.sub.7 H H 6-Br 2-CH.sub.3-4-OCF.sub.2CHF.sub.2 214-215
32 i-C.sub.3H.sub.7 H H 5,6-Br.sub.2 2-CH.sub.3-4-OCHF.sub.2
208-210 33 i-C.sub.3H.sub.7 H H 3-I 4-CF.sub.2CF.sub.2CF.sub.3
217-219 34 i-C.sub.3H.sub.7 H H 3-I 4-CF(CF.sub.3).sub.2 209-211 35
i-C.sub.3H.sub.7 H H 3-I 4-SCH.sub.2CHF.sub.2 195-197 36
i-C.sub.3H.sub.7 H H 3-I 4-SCHF.sub.2 204-206 37 i-C.sub.3H.sub.7 H
H 3-I 4-S(CF.sub.2).sub.3CF.sub.3 185-187 38 i-C.sub.3H.sub.7 H H
3-I 2-CH.sub.3-4-Cl 215-217 39 i-C.sub.3H.sub.7 H H 3-I
2-Cl-4-CF.sub.3 170-171 40 i-C.sub.3H.sub.7 H H 3-I
2-CH.sub.3-4-CF.sub.3 202-203 41 i-C.sub.3H.sub.7 H H 3-I
2-CH.sub.3-4-CF.sub.2CF.sub.3 195-196 42 i-C.sub.3H.sub.7 H H 3-I
2-CH.sub.3-4-CF.sub.2CF.sub.2CF.sub.3 193-195 43 i-C.sub.3H.sub.7 H
H 3-I 2-CH.sub.3-4-CF(CF.sub.3).sub.2 211-213 44 i-C.sub.3H.sub.7 H
H 3-I 2-CH.sub.3-4-OCF.sub.3 214-216 45 i-C.sub.3H.sub.7 H H 3-I
2-CH.sub.3-4-OCHF.sub.2 207-209 46 i-C.sub.3H.sub.7 H H 3-I
2-CH.sub.3-4- 229-231 OCH.sub.2CF.sub.2CHF.sub.2 47
i-C.sub.3H.sub.7 H H 3-I 2-CH.sub.3-4-OCF.sub.2CHFCF.sub.3 213-214
48 i-C.sub.3H.sub.7 H H 3-I 2-Cl-4-OCF.sub.3 173-175 49
i-C.sub.3H.sub.7 H H 6-I 4-SCF(CF.sub.3).sub.2 216-218 50
i-C.sub.3H.sub.7 H H 6-I 2-Cl-4-CF.sub.3 195-196 51
i-C.sub.3H.sub.7 H H 6-I 2-CH.sub.3-4-CF(CF.sub.3).sub.2 237-239 52
i-C.sub.3H.sub.7 H H 6-I 2-Cl-4-CF.sub.2CF.sub.2CF.sub.3 199-200 53
i-C.sub.3H.sub.7 H H 3-F 2-CH.sub.3-4-CF(CF.sub.3).sub.2 241-243 54
i-C.sub.3H.sub.7 H H 3-F 2-CH.sub.3-4-OCF.sub.3 183-184 55
i-C.sub.3H.sub.7 H H 3-NO.sub.2 3-F 228-230 56 i-C.sub.3H.sub.7 H H
3-NO.sub.2 2-CH.sub.3-4-OCHF.sub.2 186-188 57 n-C.sub.4H.sub.9 H H
3-NO.sub.2 2-CH.sub.3-5-Cl 172-174 58 s-C.sub.4H.sub.9 H H 6-Cl
2-CH.sub.3-4-OCHF.sub.2 213-215 59 t-C.sub.4H.sub.9 H H 3-NO.sub.2
2-CH.sub.3-4-OCHF.sub.2 172-173 60 c-C.sub.3H.sub.5 H H 3-Cl
2-CH.sub.3-4-OCHF.sub.2 156-158 61 c-C.sub.4H.sub.7 H H 3-NO.sub.2
2-CH.sub.3-5-Cl 206-208 62 c-C.sub.5H.sub.9 H H 3-NO.sub.2
2-CH.sub.3-5-Cl 200-202 63 c-C.sub.6H.sub.11 H H 3-NO.sub.2
2-CH.sub.3-5-Cl 225-227 64 CH.sub.2C.sub.3H.sub.5-c H H 3-NO.sub.2
2-CH.sub.3-5-F 190-192 65 CH.sub.2CH.sub.2Cl H H 3-NO.sub.2
2-CH.sub.3-5-F 179-181 66 CH.sub.2CH.dbd.CH.sub.2 H H 3-NO.sub.2
2-CH.sub.3-4-OCHF.sub.2 194-195 67 CH.sub.2C.ident.CH H H
3-NO.sub.2 2-CH.sub.3-4-OCHF.sub.2 190-191 68 i-C.sub.3H.sub.7 H H
3-Cl 4-CH.dbd.CBr.sub.2 209.8-214.8 69 i-C.sub.3H.sub.7 H H 6-Cl
4-CH.dbd.CCl.sub.2 199.7 70 i-C.sub.3H.sub.7 H H 3-I
4-CH.dbd.C(Cl)CF.sub.3 196.6 71 i-C.sub.3H.sub.7 H H 6-I
4-CH.dbd.C(Cl)CF.sub.3 203.3 72 t-C.sub.4H.sub.9 H H 3-I
2-CH.sub.3-4-CF.sub.2CF.sub.3 205-207 73 t-C.sub.4H.sub.9 H H 6-I
2-CH.sub.3-4-CF.sub.2CF.sub.3 216-217 74 n-C.sub.4H.sub.9 H H 6-I
2-CH.sub.3-4-CF.sub.2CF.sub.3 181.8-187.7 75 n-C.sub.5H.sub.11 H H
6-I 2-CH.sub.3-4-CF.sub.2CF.sub.3 168.7-171.3 76 i-C.sub.3H.sub.7 H
H 6-CH.sub.3 2-CH.sub.3-4-CF.sub.2CF.sub.3 177-179 77
CH.sub.2CH.sub.2OC.sub.2H.sub.5 H H 3-I
2-CH.sub.3-4-CF.sub.2CF.sub.3 146.5-150.3 78
CH.sub.2CH.sub.2OC.sub.2H.sub.5 H H 6-I
2-CH.sub.3-4-CF.sub.2CF.sub.3 157.3-160.4 79 c-C.sub.5H.sub.9 H H
6-I 2-CH.sub.3-4-CF.sub.2CF.sub.3 205.2 80 c-C.sub.6H.sub.11 H H
6-I 2-CH.sub.3-4-CF.sub.2CF.sub.3 239.0-244.4 81 i-C.sub.3H.sub.7 H
H 3-I 4-SCF.sub.3 226-227 82 i-C.sub.3H.sub.7 H H 3-NO.sub.2
4-SOCF.sub.3 202-205 83 i-C.sub.3H.sub.7 H H 3-Cl 4-SOCF.sub.3
242-244 84 i-C.sub.4H.sub.9 H H 3-I 2-CH.sub.3-4-CF.sub.2CF.sub.3
200.4-206.8 85 s-C.sub.4H.sub.9 H H 6-I
2-CH.sub.3-4-CF.sub.2CF.sub.3 216.1-218.0 86 CH(C.sub.2H.sub.5)-- H
H 3-I 2-CH.sub.3-4-CF.sub.2CF.sub.3 177 --CH.sub.2OCH.sub.3 88
CH(C.sub.2H.sub.5)-- H H 6-I 2-CH.sub.3-4-CF.sub.2CF.sub.3
198.3-201.0 --CH.sub.2OCH.sub.3 89 CH.sub.2CF.sub.3 H H 6-I
2-CH.sub.3-4-CF.sub.2CF.sub.3 184.7-202.5 90 i-C.sub.3H.sub.7 H H
3-I 3-N.dbd.C(CF.sub.2CF.sub.3)O-4 214-216 91 t-C.sub.4H.sub.9 H H
3-I 3-N.dbd.C(CF.sub.2CF.sub.3)O-4 253-254 92 i-C.sub.3H.sub.7 H H
3-Cl 2-F-4-OCF.sub.3 126-128 93 i-C.sub.3H.sub.7 H H 3-I
2-F-4-OCF.sub.3 220-222 94 i-C.sub.3H.sub.7 H H 3-I
2-C.sub.2H.sub.5-4-OCF.sub.3 241-243 95 t-C.sub.4H.sub.9 H H 3-I
2-C.sub.2H.sub.5-4-OCF.sub.3 224-225 96 i-C.sub.3H.sub.7 H H
3-Cl-4-F 2-CH.sub.3-4-OCF.sub.3 184-186 97 i-C.sub.3H.sub.7 H H
3-Cl-4-F 2-CH.sub.3-4-CF(CF.sub.3).sub.2 200-201 98
i-C.sub.3H.sub.7 H H 5-I 2-CH.sub.3-4-OCF.sub.2CHF.sub.2 203-204 99
i-C.sub.3H.sub.7 H H 4-I 2-CH.sub.3-4-CF(CF.sub.3).sub.2 215-216
100 i-C.sub.3H.sub.7 H H 3-I
2-CH.sub.3-4-C.ident.C--C.sub.4H.sub.9-t 205 101 i-C.sub.3H.sub.7 H
H 3-Cl 2-CH.sub.3-4-CN 230 102 i-C.sub.3H.sub.7 H H 3-I
2-F-4-C.sub.2F.sub.5 190 103 i-C.sub.3H.sub.7 H H 3-I
2-Cl-4-C.sub.2F.sub.5 200 104 i-C.sub.3H.sub.7 H H 3-I
2-CF.sub.3-4-C.sub.2F.sub.5 255 105 i-C.sub.3H.sub.7 H H 3-I
2-OCH.sub.3-4-C.sub.2F.sub.5 152 106 2-TetFur H H 3-Cl
2-CH.sub.3-4-C.sub.2F.sub.5 153 107 2-TetFur H H 6-Cl
2-CH.sub.3-4-C.sub.2F.sub.5 130 108 CH.sub.2-4-Pyi H H 3-Cl
2-CH.sub.3-4-C.sub.2F.sub.5 88 109 CH.sub.2-4-Pyi H H 6-Cl
2-CH.sub.3-4-C.sub.2F.sub.5 Paste 110 i-C.sub.3H.sub.7 H H 3-I
2-C.sub.2F.sub.5-4-C.sub.2F.sub.5 245 111 i-C.sub.3H.sub.7 H H H
4-O-(2-Pym) 246 112 C(CH.sub.3).sub.2CH.sub.2CH.sub.3 H H 3-I
2-CH.sub.3-4-C.sub.2F.sub.5 193 113
C(CH.sub.3).sub.2CH.sub.2CH.sub.3 H H 3-I 2-CH.sub.3-4-OCF.sub.3
180 114 C(CH.sub.3).sub.2CH.sub.2CH.sub.3 H H 3-I
2-CH.sub.3-4-OCHF.sub.2 176-177 115 i-C.sub.3H.sub.7 H H 3-I
2-Cl-4-OCF.sub.2O-5 226 116 i-C.sub.3H.sub.7 H H 3-I
2-Cl-3-OCF.sub.2CF.sub.2O-4 219 117 C(CH.sub.3).sub.2CH.sub.2Cl H H
3-I 2-CH.sub.3-4-C.sub.2F.sub.5 168-169 118 i-C.sub.3H.sub.7 H H
3-I 4-(2-CH.sub.3-4-Thz) 217 119 i-C.sub.3H.sub.7 H H 3-I
4-(2-CH.sub.3-4-Oxa) 212 120 i-C.sub.3H.sub.7 H H 3-I
4-(2-i-C.sub.3H.sub.7-4-Thz) 199 121 CH(CH.sub.3)-2-Pyi H H 3-I
2-CH.sub.3-4-OCF.sub.3 158-161 122 N(Ph)COCF.sub.3 H H 3-I
2-CH.sub.3-4-C.sub.2F.sub.5 239-241 123 CH(CH.sub.3)-2-Fur H H 3-I
2-CH.sub.3-4-C.sub.3F.sub.7-i 191 124 CH(CH.sub.3)-2-Thi H H 3-I
2-CH.sub.3-4-C.sub.3F.sub.7-i 159 125 i-C.sub.3H.sub.7 H H
3-CF.sub.3SO 2-CH.sub.3-4-C.sub.3F.sub.7-i 211-213 126
t-C.sub.4H.sub.9 H H 3-I 2-N.dbd.C(CF.sub.3)O-3 120 127
i-C.sub.3H.sub.7 H H 3-I 2-CH.sub.3-4- 218
C(CH.sub.3).dbd.NOCH.sub.3 128 t-C.sub.4H.sub.9 H H 6-CF.sub.3S
2-CH.sub.3-4-C.sub.3F.sub.7-i 245-247 129
C(CH.sub.3).sub.2CH.sub.2SCH.sub.3 H H 3-I
2-CH.sub.3-4-C.sub.3F.sub.7-i 205-206 130
C(CH.sub.3).sub.2CH.sub.2SO.sub.2CH.sub.3 H H 3-I
2-CH.sub.3-4-C.sub.3F.sub.7-i 90-95 131
C(CH.sub.3).sub.2CH.sub.2SOCH.sub.3 H H 3-I
2-CH.sub.3-4-C.sub.3F.sub.7-i 88-90 132
CH(CH.sub.3)CH.sub.2SCH.sub.3 H H 3-I 2-CH.sub.3-4-C.sub.3F.sub.7-i
197-199 133 CH(CH.sub.3)CH.sub.2SO.sub.2CH.sub.3 H H 3-I
2-CH.sub.3-4-C.sub.3F.sub.7-i 82 134 CH(CH.sub.3)CH.sub.2SOCH.sub.3
H H 3-I 2-CH.sub.3-4-C.sub.3F.sub.7-i 134 135
C(CH.sub.3).sub.2CH.sub.2SCH.sub.3 H H 3-I 2-Cl-4-OCF.sub.3 166 136
C(CH.sub.3).sub.2CH.sub.2SO.sub.2CH.sub.3 H H 3-I 2-Cl-4-OCF.sub.3
141 137 C(CH.sub.3).sub.2CH.sub.2SO.sub.2CH.sub.3 H H 3-Br
2-Cl-4-OCF.sub.3 133 138 C(CH.sub.3).sub.2CH.sub.2SC.sub.2H.sub.5 H
H 3-I 2-CH.sub.3-4-C.sub.2F.sub.5 188-189 139
C(CH.sub.3).sub.2CH.sub.2SO.sub.2C.sub.2H.sub.5 H H 3-I
2-CH.sub.3-4-C.sub.2F.sub.5 120-122 140
C(CH.sub.3).sub.2CH.sub.2SOC.sub.2H.sub.5 H H 3-I
2-CH.sub.3-4-C.sub.2F.sub.5 125-126 141
C(CH.sub.3).sub.2CH.sub.2SCH.sub.3 H H 3-Cl
2-CH.sub.3-4-C.sub.3F.sub.7-i 199-200 142
CH(CH.sub.3)CH.sub.2SCH.sub.3 H H 3-I 2-Cl-4-C.sub.3F.sub.7-i 190
In Table 1, "Ph" means a phenyl group, "c" means an alicyclic
hydrocarbon group, "Pyi" means a pyridyl group, "Pym" means a
pyrimidinyl group, "Fur" means a furyl group, "TetFur" means a
tetrahydrofuryl group, "Thi" means a thienyl group, "Thz" means a
thiazolyl group, and "Oxa" means an oxazolyl group.
[0021] As the compounds having an insecticidal, acaricidal or
nematocidal activity, which the composition for noxious
organisms-controlling agent of the present invention comprises,
insecticidal compounds such as chloronicotinyl compounds, carbamate
compounds, pyrethroid compounds, macrolide compounds, phosphorus
compounds and the like can be referred to. Examples thereof include
the following compounds indicated by their general names, however,
the present invention is by no means limited by these
compounds:
[0022] acetamiprid, pymetrozine, fenitrothion, acephate, carbaryl,
methomyl, cartap, cyhalothrin, ethofenprox, teflubenzuron,
flufenoxuron, tebufenozide, fenpyroximate, pyridaben, imidacloprid,
buprofezin, BPMC (fenobucarb), malathion, methidathion, fenthion,
diazinon, oxydeprofos, vamidothion, ethiophencarb, pirimicarb,
permethrin, cypermethrin, bifenthrin, halfenprox, silafluofen,
nitenpyram, chlorfluazuron, methoxyfenozide, tebufenpyrad,
pyrimidifen, dicofol, propargite, hexythiazox, clofentezine,
spinosad, milbemectin, BT (bacillus thuringiensis), indoxacarb,
chlorfenapyr, fipronil, etoxazole, acequinocyl, pirimiphos-methyl,
acrinathrin, quinomethionate, chlorpyrifos, avermectin,
emamectin-benzoate, fenbutatin oxide, terbufos, ethoprophos,
cadusafos, fenamiphos, fensulfothion, DSP, dichlofenthion,
fosthiazate, oxamyl, isamidofos, fosthietan, isazofos, thionazin,
benfuracarb, spirodiclofen, ethiofencarb, azinphos-methyl,
disulfoton, methiocarb, oxydemeton-methyl, parathion, cyfluthrin,
beta-cyfluthrin, tebupyrimfos, spiromesifen, endosulfan, amitraz,
tralomethrin, acetoprole, ethiprole and the like.
[0023] Further, it is also possible to use the compounds mentioned
above in combination with insecticides, acaricides and nematocides
having the following general names or chemical names, or those
disclosed in the following Patent Kokai gazettes, etc.:
[0024] ethion, trichlorfon (DEP), metamidophos, dichlorvos (DDVP),
mevinphos, monocrotophos, dimethoate, formothion, mecarbam,
thiometon, disulfoton, naled (BRP), methylparathion, cyanophos,
diamodafos, albendazole, oxibendazole, fenbendazole, oxfendazole,
propaphos, sulprofos, prothiofos, profenofos, isophenphos,
temephos, phenthoate, dimethylvinphos, chlorfenvinphos,
tetrachlorvinphos, phoxim, isoxathion, pyraclofos,
chlorpyrifos-methyl, pyridafenthion, phosalone, phosmet,
dioxabenzofos, quinalphos, pyrethrins, allethrin, prallethrin,
resmethrin, permethrin, tefluthrin, fenpropathrin,
alpha-cypermethrin, lambda-cyhalothrin, deltamethrin, fenvalerate,
esfenvalerate, flucythrinate, fluvalinate, cycloprothrin,
thiodicarb, aldicarb, alanycarb, metolcarb, xylylcarb, propoxur,
fenoxycarb, fenothiocarb, bifenazate, carbofuran, carbosulfan,
furathiocarb, diafenthiuron, diflubenzuron, hexaflumuron,
novaluron, lufenuron, chlorfluazuron, cyhexatin, Oleic acid sodium
salt, Potassium oleate, methoprene, hydroprene, binapacryl,
amitraz, chlorobenzilate, brompropylate, tetradifon, bensultap,
benzoximate, chromafenozide, endosulfan, diofenolan, tolfenpyrad,
triazamate, nicotine-sulfate, thiacloprid, thiamethoxam,
clothianidin, dinotefuran (MT 1-446), fluazinam, pyriproxyfen,
hydramethylnon, cyromazine, TPIC (tripropylisocyanurate),
thiocyclam, fenazaquin, polynactins, azadirachtin, rotenone,
Hydroxy propyl starch, mesulfenfos, phosphocarb, isoamidofos,
aldoxycarb, metam-sodium, morantel tartrate, dazomet, levamisol,
trichlamide, pyridalyl,
2-[2-(4-cyanophenyl)-1-(3-trifluoromethylphenyl)-ethylidene]-N-(4-trifluo-
romethoxyphenyl)hydrazine carboxamide and its E isomer, its Z
isomer, and mixtures of E and Z isomers at arbitrary mixing ratios,
and the substituted aminoquinazolinone (thion) derivatives or salts
thereof disclosed in JP-A-8-325239 and Japanese Patent Application
2000-334700, etc.
[0025] When the phthalamide derivative specified by the present
invention is combined with the second active ingredient of the
present invention, namely one or more compounds selected from the
compounds having an insecticidal, acaricidal or nematocidal
activity and the composition thus obtained is used as a composition
for noxious organisms-controlling agent, the amount of the active
ingredient compounds in 100 parts by weight of the composition may
be appropriately selected from a range of 0.1-50 parts by weight
and preferably 1-20 parts by weight. In the active ingredient
compounds, the ratio between the specified phthalamide and the one
or more compounds selected from the compounds having an
insecticidal, acaricidal or nematocidal activity may be
appropriately selected from a range of 0.05-2,000 parts by weight
and preferably 10-100 parts by weight of the one or more compounds
having an insecticidal, acaricidal or nematocidal activity, per one
part by weight of the specified phthalamide derivative.
[0026] When the composition for noxious organisms-controlling agent
of the present invention is put to use, the composition is used in
an appropriate solid, liquid or powdery form prepared according to
the conventional method in the pesticide making. According to the
need, adjuvants and the like are added to the composition at an
appropriate ratio. The mixture is subjected to melting, suspending,
mixing, impregnation, adsorption or adhesion, and then formed into
an appropriate preparation form such as emulsion, powder, granule,
wettable powder, flowable composition, etc. according to the
purpose, and put to use.
[0027] The composition for noxious organisms-controlling agent of
the present invention is suitable for controlling various
agricultural, forestry and horticultural pests making harm to
paddyfield rice plants, vegetables, fruit plants, flowers and
ornamental plants and the like; pests making injury on stored
grain; sanitary insect pests; nematodes, etc. As examples of the
pests, the following can be referred to:
[0028] pests belonging to HETEROPTERA of HEMIPTERA such as
plataspid bug (Megacopta punctatissimum), whitespotted larger
spined bug (Eysarcoris lewisi), whitespotted bug (Eysarcoris
parvus), southern green stink bug (Nezara viridula), brownwinged
green bug (Plautia stali), narrow squash bug (Cletus puctiger),
rice bug (Leptocorisa chinensis), bean bug (Riptortus clavatus),
rice leaf bug (Togo hemipterus), pear lace bug (Stephanitis nashi),
azelea lace bug (Stephanitis pyrioides), pale green plant bug
(Apolygus spinolai), sorghum plant bug (Stenotus rubrovittalus),
rice leaf bug (Trigonotylus coelestialium), etc.;
[0029] pests belonging to HOMOPTERA such as grape leafhopper
(Arboridia apicalis), tea green leafhopper (Empoasca onukii), green
rice leafhopper (Nephotettix cincticeps), green rice leafhopper
(Nephotettix virescens), small brown planthopper (Laodelphax
striatellus), brown rice planthopper (Nilaparvata lugens),
whitebacked rice planthopper (Sogatella furcifera), citrus psylla
(Diaphorina citri), citrus spiny whitefly (Aleurocanthus
spiniferus), silver leaf whitefly (Bemisia argentifolli),
sweetpotato whitefly (Bemisia tabaci), citrus whitefly (Dialeurodes
citri), greenhouse whitefly (Trialeurodes vaporariorum), grapeleaf
louse (Viteus vitifolli), woolly apple aphid (Eriosoma lanigerum),
spiraea aphid (Aphis citricola), cowpea aphid (Aphis craccivora),
cotton aphid (Aphis gossipii), greenhouse-potato aphid (Aulacorthum
solani), cabbage aphid (Brevicoryne brassicae), potato aphid
(Macrosiphum euphorbiae), green peach aphid (Myzus persicae), oat
bird-cherry aphid (Rhopalosiphum padi), japanese grain aphid
(Sitobion akebiae), comstock mealybug (Pseudococcus comstocki),
Inidan wax scale (Ceroplastes ceriferus), red scale (Aonidiella
aurantii), San Jose scale (Comstockaphis perniciosa), mulberry
scale (Pseudaulacapsis pentagoa), arrowedhead scale (Unaspis
yanonensis), etc.;
[0030] pests belonging to LEOPIDOPTERA such as summer fruit fortrix
(Adoxophyes orana fasciata), smaller tea tortrix (Adoxophyes
honmai), apple tortrix (Archips fuscocupreanus), peach fruit moth
(Carposina niponensis), oriental fruit moth (Grapholita molesta),
oriental tea tortrix (Homona magnanima), tea leafroller (Caloptilia
theivora), mugwort looper (Ascotis selenaria), grape berry moth
(Endopiza viteana), codling moth (Laspeyresia pomonella), apple
leafminer (Phyllonorycter ringoniella), apple leaf miner (Lyonetia
prunifoliella malinella), citrus leafminer (Phyllocnistis
citrella), diamondback moth (Plutella xylostella), pink bollworm
(Pectinophora gossypiella), peach fruit moth (Carposina
niponensis), rice stem borer (Chilo supperssalis), yellow rice
borer (Scirpophaga incertulas), rice leafroller (Cnaphalocrosis
medinalis), cabbage webworm (Hellulla undalis), Chinese yellow
swallowtail (Papilio xuthus), common white (Pieris rapae
crucivora), tent catapillar (Malacosoma neustria testacea), fall
webworm (Hyphantria cunea), bluegrass webworm (Parapediasia
tererrella), corn earworm (Helicoverpa armigera), Heliothis
(Heliothis spp.), cutworm (Agrotis segetum), beet semi-looper
(Autographa nigrisigna), cabbage armyworm (Mamestra brassicae),
beat armyworm (Spodoptera exigua), common cutworm (Spodoptera
litura), etc.;
[0031] pests belonging to COLEOPTERA such as cupreous chafer
(Anomala cuprea), Japanese beetle (Popillia japonica), powderpost
beetle (Lyctus brunneus), confused flour beetle (Tribolium
confusum), twenty-eight-spotted ladybird (Epilachna
vigintioctopunctata), whitespotted longicorn beetle (Anoplophora
malasiaca), Japanese pine sawyer (Monochamus alteratus), azuki bean
weevil (Callosobruchus chinensis), cucurbit leaf beetle
(Aulacophora femoralis), rootworm (Diabrotica spp.), boll weevil
(Anthonomus grandis grandis), Mexican beetle (Epilachna
varivestis), Colorado leaf beetle (Leptinotarsa decemlineata), rice
water weevil (Lissorhoptrus oryzophylus), rice leaf beetle (Oulema
oryzae), hunting billbug (Sphenophrus venatus vestitus), etc.;
[0032] pests belonging to HYMENOPTERA such as cabbage sawfly
(Athalia rosae ruficornis), rose argid sawfly (Arge pagana),
Formica japonica, etc.; pests belonging to DIPTERA such as rice
leafminer (Agromyza oryzae), rice leafminer (Hydrellia griseola),
legume leafminer (Liriomyza trifolii), onion maggot (Delia
antiqua), house fly (Musca domestica), Culex pipiens molestus,
house mosquito (Culex pipiens pallens), etc.;
[0033] pests belonging to THYSANOPTERA such as yellow tea thrips
(Scirtothrips dorsalis), southern yellow thrips (Thrips palmi),
onion thrips (Thrips tabaci), cirtus yellow thrips (Frankliniella
occidentalis), etc.;
[0034] pests belonging to ISOPTERA such as Formosan subterranean
termites (Coptotermes formosanus), japanese subterranean termite
(Reticulitermes speratus), booklice (Psocoptera), Liposcelis
bostrychophilus, etc.;
[0035] pests belonging to ORTHOPTERA such as rice grasshopper (Oxya
yezoensis), mole crichet (Gryllotalpa sp.), American cockroach
(Periplaneta americana), German cockroach (Blattella germanica),
etc.; pests belonging to ACARINA such as citrus red mite
(Panonychus citri), fruit tree red spider mite (Panonychus ulmi),
two-spotted spider mite (Tetranychus urticae), Kanzawa spider mite
(Tetranychus kanzawai), southern false spider mite (Brevipalpus
phoenicis), clover mite (Bryobia praetiosa), pink citrus rust mite
(Aculops pelekassi), japanese pear rust mite (Eriophyes
chibaensis), broad mite (Polyphagotarsonemus latus), bulb mite
(Rhizoglyphus robini), mold mite (Tyrophagus putrescentiae),
etc.;
[0036] pests belonging to TYLENCHIDA such as coffee root-lesion
nematode (Pratylenchus coffeae), Cobb root-lesion nematode
(Pratylenchus penetrans), potato cyst nematode (Globodera
rostochiensis), southern root-knot nematode (Meloidogyne
incognita), etc.; pests belonging to DOLYLAMIDA such as needle
nematode (Longidorus sp.), etc.; and pests belonging to GASTRPODA
such as slug (Incilaria bilineata), etc.
[0037] The useful plants to which the composition for noxious
organisms-controlling agent of the present invention can be applied
are not particularly limited, and the following plants can be
referred to as examples thereof:
[0038] cereals such as rice, barley, wheat, rye, oat, corn, etc.;
beans and peas such as soybean, red bean, broad bean, pea,
kidney-bean, peanut, etc.; fruit trees such as apple, citrus trees
and fruits, pear, grape, peach, plum, cherry, walnut, chestnut,
almond, banana, strawberry, etc.; leafy and fruit vegetables such
as cabbage, tomato, spinach, broccoli, lettuce, onion, stone-leek,
Spanish paprika, egg-plant, pepper, etc.; root crops such as
carrot, potato, sweet potato, taro, radish, lotus rhizome, turnip,
burdock, garlic, etc.; processing crops such as cotton, flax, beet,
hop, sugar can, sugar beet, olive, gum, coffee, tobacco, tea, etc.;
cucurbitaceous plants such as pumpkin, cucumber, musk melon, water
melon, melon, etc.; pasture plants such as orchard grass, sorghum,
timothy, clover, alfalfa, etc.; lawn grasses such as
mascarenegrass, bent grass, etc.; perfumery crops such as lavender,
rosemary, thyme, parsley, pepper, ginger, etc.; flowers and
ornamental plants such as chrysanthemum, rose, carnation, orchid,
etc.; garden-trees such as ginkgo tree, cherry tree, gold-leaf
plant, etc.; and timber woods such as white fir, silver fir, pine,
hatchet-leaved arbor-vitae, Japan cedar, Japanese eypress, etc.
[0039] In order to control various disease pests, the composition
for noxious organisms-controlling agent of the present invention is
applied to the plants on which appearance of the noxious organisms
is expected, either as it is or in the form of a dilution or
suspension in a proper quantity of water or the like at a dosage
effective for the control of the noxious organisms. For instance,
with the aim of controlling the appearance of noxious organisms on
fruit trees, cereals and vegetables, the composition may be
directly used for foliage treatment, or the composition may also be
used for seed treatments such as immersion of seeds in the agent
solution, seed coating, calper treatment or the like, or absorption
from the root by soil treatment or the like, such as incorporation
into total soil layer, row treatment, soil incorporation, cell
seedling treatment, prickling-in-hole treatment, plant foot
treatment, top dressing, nursery box application of rice, submerged
application, etc. In addition, application of the composition to
the nutrient solution in the water culture, the use by fumigation,
and the injection into tree stalks, etc. are also usable.
[0040] Further, apart from the spraying treatment on stored grain
pests, house pests, sanitary insect pests and forest pests,
application to construction material of house, fumigation, bait,
etc. are also adoptable.
[0041] As the method of treating seeds, a method of dipping seeds
in a diluted or undiluted liquid preparation of the liquid or solid
composition and thereby making the agent permeate into the seeds; a
method of mixing a solid or liquid preparation with seeds for the
sake of powder coating and thereby making the agent adhere to the
seed surface; a method of mixing the preparation with an adhesive
carrier such as resin, polymer or the like and coating seeds with
such an adhesive mixture; a method of spraying the preparation to
the neighborhood of seeds simultaneously with planting, etc. can be
referred to.
[0042] The term "seed" to be treated with the composition of the
present invention means a plant body of the initial stage of
cultivation used for reproduction of plants, and involves not only
the seeds but also plant bodies for nutrient reproduction such as
bulb, tuber, seed tuber, aerial tuber, scaly bulb, stalks for
cuttage, and the like.
[0043] The term "soil" or "cultivation carrier" for plants in the
practice of the using method of the present invention means a
support for use in culture of a plant and especially a support in
which roots are to be grown. They are not limited in material
quality, but any material may be used so far as a plant can be
grown therein. For instance, so-called various soils, nursery mat,
water and the like can be used. Specific examples of the material
constituting the soil or cultivation carrier include sand, pumice,
vermiculite, diatomaceous earth, agar, gelatinous materials,
polymeric materials, rock wool, glass wool, wood chips, bark and
the like.
[0044] As method for spraying the composition to foliage part of
crops or stored grain pest, sanitary insect pest, forest pest,
etc., a method of diluting a liquid preparation such as
emulsifiable concentrate, flowable agent and the like or a solid
preparation such as wettable preparation, granular wettable
preparation and the like with water properly and spraying the
dilution, a method of spraying a powdery composition, a method of
fumigation, etc. can be referred to.
[0045] As method for applying the composition to the soil, a method
of applying a liquid preparation either diluted or undiluted with
water to the plant foot, nursery bed for raising seedlings or the
like, a method of spraying a granular agent to the plant foot or
nursery bed, a method of spraying a dust, a wettable powder, a
wettable granule or a granular agent to the soil and mixing it with
the whole soil either before seeding or before transplantation, a
method of spraying a dust, a wettable powder, a wettable granule, a
granular agent or the like to planting holes, planting rows, etc.
can be referred to.
[0046] As method for applying the composition to a nursery box of
paddyfield rice, a method of applying the composition in the form
of dust, granular wettable powder, granule, etc. can be referred
to, though the preparation form may vary depending on the time of
application, namely whether the application is carried out in
sowing period, greening period or transplanting period. It is also
possible to apply the composition in the form of a mixture with
soil, as in the form of mixture of soil and a dust, a granular
wettable powder or a granule, according to a method of mixing into
bed soil, covering soil, or the whole soil. It is also possible to
apply the composition by merely making the soil and various
preparations into layers.
[0047] For applying the composition of the present invention to a
paddy field, a solid preparation such as jumbo-pack, granule,
wettable granule, and the like or a liquid preparation such as
flowable, emulsifiable concentrate and the like is scattered to a
paddy field usually in a submerged state. Otherwise, it is also
possible to scatter or inject an appropriate agent as it is or in
the form of a mixture with fertilizers into soil at the time of
transplantation. It is further possible to apply an emulsifiable
concentrate to the water inlet or water flow source of irrigating
system, by which the composition can be applied together with water
supplied to the paddy field in a labor-saving manner.
[0048] In case of upland field crops, the composition of the
present invention may be applied to the cultivation carrier
surrounding the seeds or plant bodies in the period from the
seeding to the seedling raising. In cases where plant seeds are
directly sown to the field, the composition may directly be applied
to seeds to make a seed coating, or may also be applied to the base
of hills in the course of cultivation to achieve a successful
result. It is also possible to scatter a granular preparation or to
apply a liquid preparation after dilution with water or without
dilution. Another preferable treatment is to mix a granular
preparation with a cultivation carrier before seeding and to sow
seeds thereafter.
[0049] In cases where cultured plants to be transplanted are
treated at the seeding time or in the seedling raising period, it
is preferable to treat the seeds directly, or to carry out an
irrigating treatment of a seedling raising bed with a liquefied
agent, or to carry out a powdering treatment thereof with a
granular agent. Further, it is also preferable to apply a granular
agent to the planting holes at the time of set-planting or to mix
the agent into the cultivation carrier in the neighborhood of the
sites of transplantation.
[0050] The composition for noxious organisms-controlling agent of
the present invention may be put to use after forming it into a
usual preparation form, such as emulsifiable concentrate, wettable
powder, granular wettable powder, flowable preparation, solution,
granule, dust, fumigant and the like. Although the dosage thereof
varies depending on the content of active ingredient in the
composition, climate conditions, preparation form, method of
application, place of application, objective noxious organism to be
controlled, objective crop plant, etc. The dosage may be
appropriately selected from a range of 0.1 gram to 1,000 grams and
preferably 1 gram to 500 grams in terms of weight of active
ingredient, per are of the field. In the case of seed treatment, it
is possible to use the composition in an amount of 0.01-50% and
preferably in an amount of 0.1-10% in terms of weight of active
ingredient, based on the weight of seed. In cases where an
emulsifiable concentrate or a wettable powder is diluted with water
and then put to use, the concentration at the time of application
is 0.00001-0.1%. In the cases of a granular preparation, a dust,
and a liquid composition to be applied to seeds, the composition is
directly applied without dilution, usually.
[0051] For the purpose of controlling the diseases and/or the weeds
which appear simultaneously with the time of the application of the
composition for noxious organisms-controlling agent of the present
invention, the second active ingredient of the present invention,
namely the compound having an insecticidal, acaricidal or
nematocidal activity, may be replaced with a compound having a
fungicidal or herbicidal activity. By taking such a measure, the
span of objective disease and pests to be controlled can be
expanded and the dosage can be reduced, and the herbicidal effect
can be increased synergistically. The same effect as above can be
expected also by adding a compound having a fungicidal or
herbicidal activity to the composition for noxious
organisms-controlling agent of the present invention and putting
the mixture thus obtained to use.
[0052] As said compound having a fungicidal or herbicidal activity,
the following can be referred to.
[0053] Thus, examples of the compound having a fungicidal activity
include azoxystrobin, diclocymet, pyroquilon, kasugamycin, IBP
(iprobenfos), hymexazol, mepronil, tricyclazole, edifenphos,
isoprothiolane, blasticidin, flutolanil, diclomezine, pencycuron,
carbendazim, dodine, propamocarb, pyrimethanil, fluquinconazole,
fosetyl-AL, bromoconazole, triticonazole, flumetover, fenamidone,
tolylfluanid, dichlofluanid, trifloxystrobin, triadimenol,
spiroxamine, fenhexamid, iprovalicarb, fthalide, iprodione,
thiophanate, benomyl, triflumizole, fluazinam, zineb, captan,
manzeb, fenarimol, calcium polysulfide, triadimefon, vinclozolin,
dithianon, bitertanol, polycarbamate, iminoctadine-DBS, pebulate,
polyoxin-B, propineb, chinomethionat, dichlofluanid,
chlorothalonil, difenoconazole, fluoroimide, triforine, oxadixyl,
streptomycin, mancozeb, oxolinic acid, mepronil, metalaxyl,
propiconazole, hexaconazole, sulfur, pyrifenox, basic copper
sulfate, pyrimethanil, iprobenfos, tolclofos-methyl, maneb,
thiophanate-methyl, thifluzamide, furametpyr, flusulfamide,
kresoxim-methyl, carpropamid, hydroxyisoxazole, echlomezole,
procymidone, vinclozolin, ipconazole, furconazole, myclobutanil,
tetraconazole, tebuconazole, imibenconazole, prochloraz,
pefurazoate, cyproconazole, mepanipyrim, thiadiazin, probenazole,
acibenzolar-S-methyl, validamycin(-A), fenoxanil,
N-(3-chloro-4-methylphenyl)-4-methyl-1,2,3-thiadiazole-5-carboxamide,
etc.
[0054] Examples of the compound having a herbicidal activity
include bensulfuron-methyl, azimsulfuron, cinosulfuron,
cyclosulfamuron, pyrazosulfuron-ethyl, imazosulfuron, indanofan,
cyhalofop-butyl, thenylchlor, esprocarb, etobenzanid, cafenstrole,
clomeprop, dimethametryn, daimuron, bifenox, pyributicarb,
pyriminobac-methyl, pretilachlor, bromobutide, benzofenap,
benthiocarb, bentoxazone, benfuresate, mefenacet,
fenoxaprop-P-ethyl, phenmedipham, diclofop-methyl, desmedipham,
ethofumesate, isoproturon, amidosulfuron, anilofos, ethoxysulfuron,
iodosulfuron, isoxadifen, foramsulfuron, pyraclonil, mesosulfuron,
diuron, neburon, dinoterb, carbetamide, bromoxynil, oxadiazon,
dimefuron, diflufenican, aclonifen, benzofenap, oxaziclomefone,
isoxaflutole, oxadiargyl, flurtamone, metribuzin,
methabenzthiazuron, tribufos, metamitron, ethiozin, flufenacet,
sulcotrion, fentrazamide, propoxycarbazone, flucarbazone,
metosulam, amicarbazone, etc.
[0055] Further, it is also possible to mix the herbicides expressed
by the following general names into the composition of this
invention:
[0056] glyphosate-isopropyl amine, glyphosate-trimesium,
glufosinate-ammonium, bialaphos, butamifos, prosulfocarb, asulam,
linuron, calcium peroxide, alachlor, pendimethalin,
acifluofen-sodium, lactofen, ioxynil-octanoate, alloxydim,
sethoxydim, napropamide, pyrazolate, pyraflufen-ethyl, imazapyr,
sulfentrazone, oxadiazon, paraquat, diquat, simazine, atrazine,
fluthiacet-methyl, quizalofop-ethyl, bentazone (BAS-3510-H),
triaziflam, etc.
[0057] Further, the composition of the present invention can be
used in the form of a mixture with the following compounds having a
plant growth regulating activity:
[0058] thidiazuron, mefenpyr, ethephon, cyclanilide, etc.
[0059] The composition of this invention can be used as a mixture
with the following biotic pesticides to exhibit a similar
effect:
[0060] viral preparations such as Nuclear polyhedrosis virus (NPV),
Granulosis virus (GV), Cytoplastic polyhedrosis virus (CPV),
Entomopox virus (EPV), etc.:
[0061] microbial pesticides used as insecticide or nematocide such
as Monacrosporium phymatophagum, Steinernema caprocapsae,
Steinernema kushidai, Pasteuria penetrans, etc.;
[0062] microbial pesticides used as fungicide such as Trichoderma
lignorum, Agrobacterium radiobactor, Erwinia carotovora, Bacillus
subtilis, monacrosporium.phamatophagum etc.; and
[0063] microbial pesticides used as herbicide such as Xanthomonas
capestris, etc.
[0064] Further, it is also possible to use the composition of the
present invention in combination with the following biotic
pesticides:
[0065] natural enemy organisms such as Parasitic wasp (Encarsia
formosa), Parasitic wasp (Aphidius colemani), Gall-mildge
(Aphidoletes aphidimyza), Parasitic wasp (Diglyphus isaea),
Parasitic mite (Dacnusa sibirica), Predatory mite (Phytoseiulus
persimilis), Predatory mite (Amblyseius cucumeris), Predatory bug
(Orius sauteri), etc.;
[0066] microbial pesticides such as Beauveria brongniartii), etc.;
and
[0067] pheromones such as (Z)-10-tetradecenyl=acetate,
(E,Z)-4,10-tetradecadienyl=acetate, (Z)-8-dodecenyl=acetate,
(Z)-11-tetradecenyl=acetate, (Z)-13-icosen-10-one,
(Z)-8-dodecenyl=acetate, (Z)-11-tetradecenyl=acetate,
(Z)-13-icosen-10-one, 14-methyl-1-octadecene, etc.
EXAMPLES
[0068] Next, typical examples and test examples of the present
invention are mentioned below. This invention is by no means
limited by these examples. In the examples, the terms "part" and
"parts" are both by weight.
Example 1
TABLE-US-00002 [0069] Compound of Table 1 5 parts Fenpyroximate 10
parts Silicic acid hydrate 30 parts Hitenol N-08 (manufactured by 5
parts Daiichi Kogyo Seiyaku) Calcium ligninsulfonate 3 parts
Wettable clay 47 parts
[0070] After impregnating silicic acid hydrate with the active
ingredient compounds, the silicic acid hydrate is uniformly blended
with other ingredients to form a wettable powder composition.
Example 2
TABLE-US-00003 [0071] Compound of Table 1 10 parts Tebufenpyrad 10
parts Sorpol 3105 (manufactured by 5 parts Toho Yakuhin Kogyo)
Propylene glycol 5 parts Rhodopol (manufactured by 2 parts Rohne
Poulenc Inc.) Water 68 parts
[0072] The above-mentioned ingredients are uniformly mixed together
and dispersed in water to form a flowable preparation.
Example 3
TABLE-US-00004 [0073] Compound of Table 1 10 parts Isoprothiolane
20 parts SP-3005X (manufactured by 15 parts Toho Kagaku) Xylene 35
parts N-Methylpyrrolidone 20 parts
[0074] The above-mentioned ingredients are uniformly mixed and
melted to form an emulsifiable concentrate.
Example 4
TABLE-US-00005 [0075] Compound of Table 1 10 parts Tebufenozide 20
parts Sorpol 3105 5 parts Propylene glycol 2 parts Rhodopol 23 1
part Water 62 parts
[0076] The above-mentioned ingredients are uniformly mixed together
and dispersed in water to form a flowable preparation.
Example 5
TABLE-US-00006 [0077] Compound of Table 1 10 parts Buprofezin 5
parts Silicic acid hydrate 34 parts Hitenol N-08 3 parts Demol T 2
parts Calcium carbonate powder 46 parts
[0078] After impregnating silicic acid hydrate with the active
ingredient compounds, the silicic acid hydrate is uniformly blended
with other ingredients to form a wettable powder composition.
Example 6
TABLE-US-00007 [0079] Compound of Table 1 10 parts Pyridaben 15
parts SP-3005X 15 parts Xylene 40 parts N-Methylpyrrolidone 20
parts
[0080] The above-mentioned ingredients are uniformly mixed together
and melted to form an emulsifiable concentrate.
Example 7
TABLE-US-00008 [0081] Compound of Table 1 10 parts Pyraflufen-ethyl
20 parts Sorpol 3105 5 parts Propylene glycol 2 parts Rhodopol 23
0.5 part Water 62.5 parts
[0082] The above-mentioned ingredients are uniformly mixed together
and dispersed in water to form a flowable preparation.
Example 8
TABLE-US-00009 [0083] Compound of Table 1 10 parts Acetamiprid 5
parts Sorpol 3105 5 parts Propylene glycol 3 parts Rhodopol 2 parts
Water 75 parts
[0084] The above-mentioned ingredients are uniformly mixed together
and dispersed in water to form a flowable preparation.
Example 9
TABLE-US-00010 [0085] Compound of Table 1 10 parts Imidacloprid 10
parts SP-3005X 15 parts Xylene 45 parts N-Methylpyrrolidone 20
parts
[0086] The above-mentioned ingredients are uniformly mixed together
and melted to form an emulsifiable concentrate.
Example 10
TABLE-US-00011 [0087] Compound of Table 1 5 parts Chlorfenapyr 10
parts Sorpol 3105 5 parts Propylene glycol 3 parts Rhodopol 23 2
parts Water 75 parts
[0088] The above-mentioned ingredients are uniformly mixed together
and dispersed in water to form a flowable preparation.
Example 11
TABLE-US-00012 [0089] Compound of Table 1 5 parts Pymetrozine 10
parts Sorpol 3105 5 parts Propylene glycol 3 parts Rhodopol 23 2
parts Water 75 parts
[0090] The above-mentioned ingredients are uniformly mixed together
and dispersed in water to form a flowable preparation.
Test Example 1
Insecticidal Test on Smaller Tea Tortrix (Adoxophyes orana
fosciota)
[0091] Tea leaves were dipped in a solution of a chemical diluted
to a prescribed concentration for 30 seconds. After air-dryness,
the leaves were transferred to a plastic dish having a diameter of
9 cm, inoculated with ten 4th instar larvae of smaller tea tortrix,
and left to stand in a thermostatted chamber at 25.degree. C. Four
days and seven days after the treatment, the number of alive
insects were counted, from which percentage of death was
calculated. The test was carried out with two replications of 10
insects. The results are shown in Table 2.
TABLE-US-00013 TABLE 2 Death rate (%) Concen- After After tration 4
7 Test agent (ppm) days days Compound 19 + chlorpyriphos 0.3 + 1 35
75 + chlorfluazuron 0.3 + 1 35 95 + chlorfenapyr 0.3 + 1 30 75 +
emamectin- .sup. 0.3 + 0.1 25 85 benzoate + methoxyfenozide .sup.
0.3 + 0.1 75 95 + indoxacarb 0.3 + 1 55 95 + fenpyroximate 0.3 + 50
30 85 Compound 20 + chlorpyriphos 0.3 + 1 20 45 + chlorfluazuron
0.3 + 1 25 85 + chlorfenapyr 0.3 + 1 20 75 + emamectin- .sup. 0.3 +
0.1 25 75 benzoate + methoxyfenozide .sup. 0.3 + 0.1 45 85 +
indoxacarb 0.3 + 1 45 75 + fenpyroximate 0.3 + 50 30 80 Compound 39
+ chlorpyriphos 0.3 + 1 15 45 + chlorfluazuron 0.3 + 1 20 75 +
chlorfenapyr 0.3 + 1 15 70 + emamectin- .sup. 0.3 + 0.1 20 70
benzoate + methoxyfenozide .sup. 0.3 + 0.1 40 80 + indoxacarb 0.3 +
1 40 70 + fenpyroximate 0.3 + 50 25 75 Compound 40 + chlorpyriphos
0.3 + 1 20 45 + chlorfluazuron 0.3 + 1 25 80 + chlorfenapyr 0.3 + 1
15 70 + emamectin- .sup. 0.3 + 0.1 20 70 benzoate + methoxyfenozide
.sup. 0.3 + 0.1 35 85 + indoxacarb 0.3 + 1 35 75 + fenpyroximate
0.3 + 50 20 70 Compound 41 + chlorpyriphos 0.3 + 1 40 80 +
chlorfluazuron 0.3 + 1 35 95 + chlorfenapyr 0.3 + 1 30 75 +
emamectin- .sup. 0.3 + 0.1 30 100 benzoate + methoxyfenozide .sup.
0.3 + 0.1 75 95 + indoxacarb 0.3 + 1 55 95 + fenpyroximate 0.3 + 50
35 90 Compound 42 + chlorpyriphos 0.3 + 1 45 85 + chlorfluazuron
0.3 + 1 35 100 + chlorfenapyr 0.3 + 1 30 85 + emamectin- .sup. 0.3
+ 0.1 30 100 benzoate + methoxyfenozide .sup. 0.3 + 0.1 75 95 +
indoxacarb 0.3 + 1 55 95 + fenpyroximate 0.3 + 50 30 85 Compound 43
+ chlorpyriphos 0.3 + 1 45 85 + chlorfluazuron 0.3 + 1 35 95 +
chlorfenapyr 0.3 + 1 30 85 + emamectin- .sup. 0.3 + 0.1 30 100
benzoate + methoxyfenozide .sup. 0.3 + 0.1 75 95 + indoxacarb 0.3 +
1 50 95 + fenpyroximate 0.3 + 50 35 90 Compound 44 + chlorpyriphos
0.3 + 1 25 65 + chlorfluazuron 0.3 + 1 30 85 + chlorfenapyr 0.3 + 1
25 80 + emamectin- .sup. 0.3 + 0.1 25 75 benzoate + methoxyfenozide
.sup. 0.3 + 0.1 45 90 + indoxacarb 0.3 + 1 45 80 Compound 45 +
chlorpyriphos 0.3 + 1 30 75 + chlorfluazuron 0.3 + 1 25 90 +
chlorfenapyr 0.3 + 1 20 75 + emamectin- .sup. 0.3 + 0.1 30 80
benzoate + methoxyfenozide .sup. 0.3 + 0.1 35 85 + indoxacarb 0.3 +
1 35 75 Compound 46 + chlorpyriphos 0.3 + 1 20 65 + chlorfluazuron
0.3 + 1 35 80 + chlorfenapyr 0.3 + 1 20 75 + emamectin- .sup. 0.3 +
0.1 25 85 benzoate + methoxyfenozide .sup. 0.3 + 0.1 35 85 +
indoxacarb 0.3 + 1 40 75 Compound 47 + chlorpyriphos 0.3 + 1 40 80
+ chlorfluazuron 0.3 + 1 40 95 + chlorfenapyr 0.3 + 1 35 95 +
emamectin- .sup. 0.3 + 0.1 40 95 benzoate + methoxyfenozide .sup.
0.3 + 0.1 75 100 + indoxacarb 0.3 + 1 45 90 + fenpyroximate 0.3 +
50 35 95 Compound 48 + chlorpyriphos 0.3 + 1 25 75 + chlorfluazuron
0.3 + 1 35 85 + chlorfenapyr 0.3 + 1 35 80 + emamectin- .sup. 0.3 +
0.1 30 90 benzoate + methoxyfenozide .sup. 0.3 + 0.1 40 75 +
indoxacarb 0.3 + 1 35 80 Compound 54 + chlorpyriphos 0.3 + 1 30 80
+ chlorfluazuron 0.3 + 1 25 85 + chlorfenapyr 0.3 + 1 30 85 +
emamectin- .sup. 0.3 + 0.1 30 95 benzoate + methoxyfenozide .sup.
0.3 + 0.1 35 80 + indoxacarb 0.3 + 1 30 85 Compound 129 +
chlorpyriphos 0.1 + 1 35 75 + chlorfluazuron 0.1 + 1 35 95 +
chlorfenapyr 0.1 + 1 30 75 + emamectin- .sup. 0.1 + 0.1 25 85
benzoate + methoxyfenozide .sup. 0.1 + 0.1 75 95 + indoxacarb 0.1 +
1 55 95 + fenpyroximate 0.1 + 50 30 85 Compound 130 + chlorpyriphos
0.1 + 1 35 75 + chlorfluazuron 0.1 + 1 35 95 + chlorfenapyr 0.1 + 1
30 75 + emamectin- .sup. 0.1 + 0.1 25 85 benzoate + methoxyfenozide
.sup. 0.1 + 0.1 75 95 + indoxacarb 0.1 + 1 55 95 + fenpyroximate
0.1 + 50 30 85 Compound 131 + chlorpyriphos 0.1 + 1 35 75 +
chlorfluazuron 0.1 + 1 35 95 + chlorfenapyr 0.1 + 1 30 75 +
emamectin- .sup. 0.1 + 0.1 25 85 benzoate + methoxyfenozide .sup.
0.1 + 0.1 75 95 + indoxacarb 0.1 + 1 55 95 + fenpyroximate 0.1 + 50
30 85 Compound 19 0.3 0 30 Compound 20 0.3 0 25 Compound 39 0.3 0
20 Compound 40 0.3 0 25 Compound 41 0.3 0 30 Compound 42 0.3 0 30
Compound 43 0.3 0 35 Compound 44 0.3 0 20 Compound 45 0.3 0 25
Compound 46 0.3 0 15 Compound 47 0.3 0 30 Compound 48 0.3 0 25
Compound 54 0.3 0 25 Compound 129 0.1 10 30 Compound 130 0.1 10 25
Compound 131 0.1 5 20 chlorpyriphos 1 10 10 chlorfluazuron 1 10 30
chlorfenapyr 1 0 0 emamectin- 0.1 10 45 benzoate methoxyfenozide
0.1 0 50 indoxacarb 1 10 40 fenpyroximate 50 0 0 Untreated plot --
0 0
Test Example 2
Insecticidal Test on Green Peach Aphid (Myzus persicae)
[0092] Chinese cabbage plants (variety: Aichi) were planted in
plastic pots having a diameter of 8 cm and a height of 8 cm, on
which green peach aphids were inoculated. Then, a solution of an
agent which had been diluted to a predetermined concentration was
thoroughly sprayed to the leaves and stalks. After air-dryness, the
pots were left to stand in a green house. Six days after the
spraying treatment, the number of the insects parasitic on each
Chinese cabbage plant was counted, from which the control value was
calculated according to the following equation. The test was
carried out with two replications on one pot per one plot.
Controlling value=100-{(Ta.times.Cb)/(Tb.times.Ca)}.times.100
[0093] Ta: Number of parasitic insects after spraying in the
treated plot [0094] Tb: Number of parasitic insects before spraying
in the treated plot [0095] Ca: Number of parasitic insects after
spraying in the untreated plot [0096] Cb: Number of parasitic
insects before spraying in the untreated plot
[0097] The results are shown in Table 3.
TABLE-US-00014 TABLE 3 Concen- Control tration degree Test agent
(ppm) (%) Compound 19 + Acephate 100 + 10 81 + imidacloprid 100 +
0.1 100 + bifenthrin 100 + 0.1 100 + flufenoxuron 100 + 50 43 +
pyridaben 100 + 10 92 + milbemectin 100 + 1 100 Compound 20 +
Acephate 100 + 10 81 + imidacloprid 100 + 0.1 100 + bifenthrin 100
+ 0.1 100 + flufenoxuron 100 + 50 52 + pyridaben 100 + 10 92 +
milbemectin 100 + 1 94 Compound 39 + Acephate 100 + 10 83 +
imidacloprid 100 + 0.1 97 + bifenthrin 100 + 0.1 100 + flufenoxuron
100 + 50 48 + pyridaben 100 + 10 92 + milbemectin 100 + 1 94
Compound 40 + Acephate 100 + 10 86 + imidacloprid 100 + 0.1 100 +
bifenthrin 100 + 0.1 100 + flufenoxuron 100 + 50 48 + pyridaben 100
+ 10 92 + milbemectin 100 + 1 100 Compound 41 + Acephate 100 + 10
95 + imidacloprid 100 + 0.1 100 + bifenthrin 100 + 0.1 100 +
flufenoxuron 100 + 50 60 + pyridaben 100 + 10 88 + milbemectin 100
+ 1 98 Compound 42 + Acephate 100 + 0 95 + imidacloprid 100 + 0.1
100 + bifenthrin 100 + 0.1 100 + flufenoxuron 100 + 50 55 +
pyridaben 100 + 10 90 + milbemectin 100 + 1 100 Compound 43 +
Acephate 100 + 10 90 + imidacloprid 100 + 0.1 95 + bifenthrin 100 +
0.1 100 + flufenoxuron 100 + 50 60 + pyridaben 100 + 10 85 +
milbemectin 100 + 1 100 Compound 44 + Acephate 100 + 10 75 +
imidacloprid 100 + 0.1 80 + bifenthrin 100 + 0.1 95 + flufenoxuron
100 + 50 55 + pyridaben 100 + 10 73 + milbemectin 100 + 1 93
Compound 45 + Acephate 100 + 10 70 + imidacloprid 100 + 0.1 78 +
bifenthrin 100 + 0.1 93 + flufenoxuron 100 + 50 61 + pyridaben 100
+ 10 78 + milbemectin 100 + 1 98 Compound 46 + Acephate 100 + 10 65
+ imidacloprid 100 + 0.1 75 + bifenthrin 100 + 0.1 94 +
flufenoxuron 100 + 50 55 + pyridaben 100 + 10 68 + milbemectin 100
+ 1 95 Compound 47 + Acephate 100 + 10 78 + imidacloprid 100 + 0.1
88 + bifenthrin 100 + 0.1 94 + flufenoxuron 100 + 50 58 + pyridaben
100 + 10 75 + milbemectin 100 + 1 94 Compound 48 + Acephate 100 +
10 66 + imidacloprid 100 + 0.1 93 + bifenthrin 100 + 0.1 96 +
flufenoxuron 100 + 50 48 + pyridaben 100 + 10 75 + milbemectin 100
+ 1 90 Compound 54 + Acephate 100 + 10 65 + imidacloprid 100 + 0.1
92 + bifenthrin 100 + 0.1 89 + flufenoxuron 100 + 50 55 + pyridaben
100 + 10 73 + milbemectin 100 + 1 95 Compound 129 + Acephate 100 +
10 85 + imidacloprid 100 + 0.1 100 + bifenthrin 100 + 0.1 100 +
flufenoxuron 100 + 50 45 + pyridaben 100 + 10 90 + milbemectin 100
+ 1 100 Compound 130 + Acephate 100 + 10 87 + imidacloprid 100 +
0.1 100 + bifenthrin 100 + 0.1 100 + flufenoxuron 100 + 50 54 +
pyridaben 100 + 10 96 + milbemectin 100 + 1 95 Compound 131 +
Acephate 100 + 10 81 + imidacloprid 100 + 0.1 99 + bifenthrin 100 +
0.1 97 Compound 19 100 0 Compound 20 100 0 Compound 39 100 0
Compound 40 100 0 Compound 41 100 0 Compound 42 100 0 Compound 43
100 0 Compound 44 100 0 Compound 45 100 0 Compound 46 100 0
Compound 47 100 0 Compound 48 100 0 Compound 54 100 0 Compound 129
100 5 Compound 130 100 10 Compound 131 100 0 acephate 10 48
imidacloprid 0.1 69 bifenthrin 0.1 80 flufenoxuron 50 11 pyridaben
10 43 milbemectin 1 82
Test Example 3
Insecticidal Test on Brown Rice Planthopper (Nilaparvata
lugens)
[0098] Rice seedlings (variety: Nihombare) were dipped in a
solution of an agent diluted to a predetermined concentration for
30 seconds. After air-dryness, each seedling was introduced into a
glass-made test tube having a diameter of 1.8 cm and a height of 20
cm, and inoculated with ten 3rd inster nimphs of brown rice
planthopper. Then, the test tube was stoppered with cotton. One day
after and four days after the treatment, the number of alive
insects was counted, based on which the insect death rate was
calculated. The test was carried out with two replications of 10
heads.
[0099] The results are shown in Table 4.
TABLE-US-00015 TABLE 4 Death rate (%) Concen- After After tration 1
5 Test agent (ppm) days days Compound 19 + buprofezin 100 + 0.3 15
75 + pymetrozin 100 + 100 20 85 + silafluofen 100 + 1.sup. 95 100 +
imidacloprid 100 + 0.1 85 100 Compound 20 + buprofezin 100 + 0.3 10
80 + pymetrozin 100 + 100 25 90 + silafluofen 100 + 1.sup. 85 90 +
imidacloprid 100 + 0.1 65 95 Compound 39 + buprofezin 100 + 0.3 15
70 + pymetrozin 100 + 100 30 85 + silafluofen 100 + 1.sup. 85 85 +
imidacloprid 100 + 0.1 65 95 Compound 40 + buprofezin 100 + 0.3 20
75 + pymetrozin 100 + 100 25 90 + silafluofen 100 + 1.sup. 90 95 +
imidacloprid 100 + 0.1 75 95 Compound 41 + buprofezin 100 + 0.3 15
100 + pymetrozin 100 + 100 30 90 + silafluofen 100 + 1.sup. 85 95 +
imidacloprid 100 + 0.1 85 100 Compound 42 + buprofezin 100 + 0.3 25
100 + pymetrozin 100 + 100 35 95 + silafluofen 100 + 1.sup. 85 95 +
imidacloprid 100 + 0.1 90 100 Compound 43 + buprofezin 100 + 0.3 30
100 + pymetrozin 100 + 100 40 95 + silafluofen 100 + 1.sup. 90 100
+ imidacloprid 100 + 0.1 90 100 Compound 44 + buprofezin 100 + 0.3
15 95 + pymetrozin 100 + 100 25 95 + silafluofen 100 + 1.sup. 75 80
+ imidacloprid 100 + 0.1 80 95 Compound 45 + buprofezin 100 + 0.3
20 95 + pymetrozin 100 + 100 30 100 + silafluofen 100 + 1.sup. 80
80 + imidacloprid 100 + 0.1 85 90 Compound 46 + buprofezin 100 +
0.3 15 80 + pymetrozin 100 + 100 25 90 + silafluofen 100 + 1.sup.
75 75 + imidacloprid 100 + 0.1 70 75 Compound 47 + buprofezin 100 +
0.3 20 75 + pymetrozin 100 + 100 30 85 + silafluofen 100 + 1.sup.
65 70 + imidacloprid 100 + 0.1 70 85 Compound 48 + buprofezin 100 +
0.3 25 85 + pymetrozin 100 + 100 35 90 + silafluofen 100 + 1.sup.
70 75 + imidacloprid 100 + 0.1 75 80 Compound 54 + buprofezin 100 +
0.3 15 75 + pymetrozin 100 + 100 30 75 + silafluofen 100 + 1.sup.
65 65 + imidacloprid 100 + 0.1 80 88 Compound 129 + buprofezin 100
+ 0.3 15 80 + pymetrozin 100 + 100 15 90 + silafluofen 100 + 1.sup.
90 100 + imidacloprid 100 + 0.1 85 100 Compound 130 + buprofezin
100 + 0.3 20 85 + pymetrozin 100 + 100 25 90 + silafluofen 100 +
1.sup. 90 95 + imidacloprid 100 + 0.1 90 95 Compound 131 +
buprofezin 100 + 0.3 25 85 + pymetrozin 100 + 100 20 85 +
silafluofen 100 + 1.sup. 95 100 + imidacloprid 100 + 0.1 85 100
Compound 19 100 0 0 Compound 20 100 0 0 Compound 39 100 0 0
Compound 40 100 0 0 Compound 41 100 0 0 Compound 42 100 0 0
Compound 43 100 0 0 Compound 44 100 0 0 Compound 45 100 0 0
Compound 46 100 0 0 Compound 47 100 0 0 Compound 48 100 0 0
Compound 54 100 0 0 Compound 129 100 0 0 Compound 130 100 0 0
Compound 131 100 0 0 buprofezin 0.3 0 45 pymetrozin 100 10 40
silafluofen 1 30 30 imidacloprid 0.1 35 35 Untreated plot -- 0
5
Test Example 4
Insecticidal Test on Resistant Strain of Two-Spotted Spider
Mite
[0100] A plastic-made cup having a diameter of 8 cm was filled with
water and covered with a lid having a hole having a diameter of 1
cm. A notched filter paper was placed over the lid, and a part of
the filter paper was hung down from the lid into the water to
maintain the filter paper always in a wet state by the capillary
phenomenon.
[0101] A leaf disk prepared from the first leaves of kidney bean
(variety: Topcrop) was placed on the filter paper, and inoculated
with 10 female adults of resistant strain of two-spotted spider
mite. On a turn table, 50 ml of an agent solution diluted to a
predetermined concentration was uniformly sprayed. After the
spraying treatment, the whole was left to stand in a thermostatted
chamber at 25.degree. C.
[0102] Two days after the spraying treatment, the number of alive
spider mites were counted, based on which the spider mites death
rate were calculated. The test was carried out with two
replications of 10 adults. The results are shown in Table 5.
TABLE-US-00016 TABLE 5 Concen- Death tration rate Test agent (ppm)
(%) Compound 19 + tebufenpyrad 100 + 100 95 + fenbutatin oxide 100
+ 100 90 + halfenprox 100 + 100 85 Compound 20 + tebufenpyrad 100 +
100 90 + fenbutatin oxide 100 + 100 85 + halfenprox 100 + 100 90
Compound 39 + tebufenpyrad 100 + 100 85 + fenbutatin oxide 100 +
100 75 + halfenprox 100 + 100 90 Compound 40 + tebufenpyrad 100 +
100 85 + fenbutatin oxide 100 + 100 90 + halfenprox 100 + 100 95
Compound 41 + tebufenpyrad 100 + 100 90 + fenbutatin oxide 100 +
100 95 + halfenprox 100 + 100 85 Compound 42 + tebufenpyrad 100 +
100 95 + fenbutatin oxide 100 + 100 90 + halfenprox 100 + 100 90
Compound 43 + tebufenpyrad 100 + 100 95 + fenbutatin oxide 100 +
100 90 + halfenprox 100 + 100 95 Compound 44 + tebufenpyrad 100 +
100 85 + fenbutatin oxide 100 + 100 95 + halfenprox 100 + 100 90
Compound 45 + tebufenpyrad 100 + 100 75 + fenbutatin oxide 100 +
100 80 + halfenprox 100 + 100 75 Compound 46 + tebufenpyrad 100 +
100 95 + fenbutatin oxide 100 + 100 90 + halfenprox 100 + 100 80
Compound 47 + tebufenpyrad 100 + 100 85 + fenbutatin oxide 100 +
100 85 + halfenprox 100 + 100 75 Compound 48 + tebufenpyrad 100 +
100 90 + fenbutatin oxide 100 + 100 85 + halfenprox 100 + 100 95
Compound 54 + tebufenpyrad 100 + 100 80 + fenbutatin oxide 100 +
100 85 + halfenprox 100 + 100 90 Compound 129 + tebufenpyrad 100 +
100 95 + fenbutatin oxide 100 + 100 85 + halfenprox 100 + 100 85 +
spirodiclofen 100 + 10 90 Compound 130 + tebufenpyrad 100 + 100 90
+ fenbutatin oxide 100 + 100 95 + halfenprox 100 + 100 80 +
spirodiclofen 100 + 10 75 Compound 131 + tebufenpyrad 100 + 100 95
+ fenbutatin oxide 100 + 100 85 + halfenprox 100 + 100 90 +
spirodiclofen 100 + 10 85 Compound 19 100 0 Compound 20 100 0
Compound 39 100 0 Compound 40 100 0 Compound 41 100 0 Compound 42
100 0 Compound 43 100 0 Compound 44 100 0 Compound 45 100 0
Compound 46 100 0 Compound 47 100 0 Compound 48 100 0 Compound 54
100 0 Compound 129 100 5 Compound 130 100 10 Compound 131 100 5
tebufenpyrad 100 60 fenbutatin oxide 100 50 halfenprox 100 35
Untreated plot -- 0
Test Example 5
Test for the Effect on Southern Root-Knot Nematode (Meloidogyne
incognita)
[0103] Two killograms of a soil polluted with southern root-knot
nematode was blended with a predetermined dose of a granular
preparation. The mixture was filled into a 1/5,000 are Wagner pot.
After sowing melon seeds and carrying out the treatment of the
present invention, the pot was left to stand in a greenhouse. Sixty
days after the treatment, 25 g of the soil was sampled out, the
nematode was separated therefrom according to the method of Berman,
and the numbers of nematodes were counted after 48 hours. The test
was carried out with two replications, on one pot/group.
[0104] The results are shown in Table 6. In the tables, "ai" means
active ingredient.
TABLE-US-00017 TABLE 6 Number of nematodes Dosage per 25 g of Test
agent (g ai/10a) soil sample Compound 19 + oxamyl 300 + 300 3 +
fosthiazate 300 + 300 1 Compound 20 + oxamyl 300 + 300 4 +
fosthiazate 300 + 300 2 Compound 39 + oxamyl 300 + 300 5 +
fosthiazate 300 + 300 1 Compound 40 + oxamyl 300 + 300 4 +
fosthiazate 300 + 300 3 Compound 41 + oxamyl 300 + 300 3 +
fosthiazate 300 + 300 2 Compound 42 + oxamyl 300 + 300 7 +
fosthiazate 300 + 300 5 Compound 43 + oxamyl 300 + 300 6 +
fosthiazate 300 + 300 2 Compound 44 + oxamyl 300 + 300 5 +
fosthiazate 300 + 300 5 Compound 45 + oxamyl 300 + 300 4 +
fosthiazate 300 + 300 2 Compound 46 + oxamyl 300 + 300 1 +
fosthiazate 300 + 300 3 Compound 47 + oxamyl 300 + 300 5 +
fosthiazate 300 + 300 3 Compound 48 + oxamyl 300 + 300 4 +
fosthiazate 300 + 300 2 Compound 54 + oxamyl 300 + 300 4 +
fosthiazate 300 + 300 2 Compound 129 + oxamyl 300 + 300 8 +
fosthiazate 300 + 300 2 Compound 130 + oxamyl 300 + 300 5 +
fosthiazate 300 + 300 1 Compound 131 + oxamyl 300 + 300 6 +
fosthiazate 300 + 300 3 Compound 19 300 36 Compound 20 300 28
Compound 39 300 34 Compound 40 300 33 Compound 41 300 31 Compound
42 300 28 Compound 43 300 36 Compound 44 300 29 Compound 45 300 30
Compound 46 300 36 Compound 47 300 27 Compound 48 300 33 Compound
54 300 32 Compound 129 300 45 Compound 130 300 40 Compound 131 300
41 oxamyl 300 13 fosthiazate 300 7 Untreated group -- 33
Test Example 6
Test for the Control of Rice Water Weevil (Lissorhoptrus
oryzophilus) and Rice Blast on Paddyfield Rice Plant by Nursery Box
Application
[0105] Fifty grams of a granular preparation was applied to rice
plant (variety: Koshihikari) cultured in a nursery box. On the same
day as the day of treatment (in the middle ten days of May), the
rice plant was transplanted to the main paddy field. The
controlling effect against rice water weevil was evaluated by
investigating the number of hills classified by the extent of
injury, on 100 hills in each plot, 21 days after the
transplantation, and calculating the overall extent of injury
therefrom. The controlling effect against rice blast was evaluated
by investigating the areal rate of disease spot 60 days after the
transplantation.
Extent of injury={(4A+3B+2C+D)/(4.times.N)}.times.100
wherein
[0106] A: percentage of injured leaves: 91% or higher
[0107] B: percentage of injured leaves: 61-90%
[0108] C: percentage of injured leaves: 31-60%
[0109] D: percentage of injured leaves: 1-30%
[0110] N: Number of hills investigated
[0111] The results are shown in Table 7.
TABLE-US-00018 TABLE 7 Areal rate of Extent disease Dosage of
injury spot (%) (g ai/ After After Test agent Box) 21 days 60 days
Compound 19 + imidacloprid 0.5 + 1 + 2 3.5 0.4 + carpropamid
Compound 20 + imidacloprid 0.5 + 1 + 2 2.3 0.3 + carpropamid
Compound 39 + imidacloprid 0.5 + 1 + 2 1.5 0.1 + carpropamid
Compound 40 + imidacloprid 0.5 + 1 + 2 2.5 0.6 + carpropamid
Compound 41 + imidacloprid 0.5 + 1 + 2 1.3 0.2 + carpropamid
Compound 42 + imidacloprid 0.5 + 1 + 2 2.5 0.2 + carpropamid
Compound 43 + imidacloprid 0.5 + 1 + 2 1.3 0.1 + carpropamid
Compound 44 + imidacloprid 0.5 + 1 + 2 3.8 0.4 + carpropamid
Compound 45 + imidacloprid 0.5 + 1 + 2 2.2 0.3 + carpropamid
Compound 46 + imidacloprid 0.5 + 1 + 2 1.8 0.4 + carpropamid
Compound 47 + imidacloprid 0.5 + 1 + 2 2.8 0.2 + carpropamid
Compound 48 + imidacloprid 0.5 + 1 + 2 1.9 0.5 + carpropamid
Compound 54 + imidacloprid 0.5 + 1 + 2 1.3 0.6 + carpropamid
Compound 129 + imidacloprid 0.5 + 1 + 2 3.5 0.5 + carpropamid
Compound 130 + imidacloprid 0.5 + 1 + 2 2.9 0.4 + carpropamid
Compound 131 + imidacloprid 0.5 + 1 + 2 3.2 0.3 + carpropamid
Compound 19 0.5 38.9 8.3 Compound 20 0.5 37.4 8.1 Compound 39 0.5
38.9 8.2 Compound 40 0.5 39.0 7.9 Compound 41 0.5 43.2 8.5 Compound
42 0.5 39.5 8.3 Compound 43 0.5 44.3 8.9 Compound 44 0.5 45.9 9.1
Compound 45 0.5 38.8 8.2 Compound 46 0.5 42.7 8.5 Compound 47 0.5
40.9 7.8 Compound 48 0.5 39.8 7.4 Compound 54 0.5 41.7 9.0 Compound
129 0.5 40.3 9.1 Compound 130 0.5 39.0 8.3 Compound 131 0.5 41.2
8.3 imidacloprid + carpropamid 1 + 2 5.8 1.2 Untreated plot -- 45.6
8.2
Test Example 7
Test for the Control of Small Brown Planthopper (Laodelphax
striatellus) and Rice Leafroller (Cnaphalocrosis medinalis) on
Paddyfield Rice Plant by Nursery Box Application
[0112] Fifty grams of a granular preparation was applied to rice
plant (variety: Nihombare) cultured in a nursery box, after which
the rice plant was transplanted to the main paddy field (in the
middle of May). The controlling effect against small brown
planthopper was evaluated by investigating the number of parasitic
insects on 30 hills per each plot, 40 days and 60 days after the
transplantation. The controlling effect against rice leafroller was
evaluated by investigating the number of injured leaves on 100
hills per each plot, 50 days after the transplantation.
[0113] The results are shown in Table 8.
TABLE-US-00019 TABLE 8 Percent- Number of age of parasitic injured
planthoppers per leaves Dosage 30 hills (%) (g ai/ After After
After Test agent Box) 40 days 60 days 50 days Compound 19 +
imidacloprid 0.5 + 1.sup. 0 4 0.03 + benfuracarb 0.5 + 2.5 17 48
0.07 Compound 20 + imidacloprid 0.5 + 1.sup. 0 7 0.05 + benfuracarb
0.5 + 2.5 22 55 0.08 Compound 39 + imidacloprid 0.5 + 1.sup. 0 9
0.04 + benfuracarb 0.5 + 2.5 24 45 0.07 Compound 40 + imidacloprid
0.5 + 1.sup. 0 10 0.02 + benfuracarb 0.5 + 2.5 17 54 0.08 Compound
41 + imidacloprid 0.5 + 1.sup. 0 6 0.04 + benfuracarb 0.5 + 2.5 33
34 0.06 Compound 42 + imidacloprid 0.5 + 1.sup. 0 7 0.03 +
benfuracarb 0.5 + 2.5 31 65 0.08 Compound 43 + imidacloprid 0.5 +
1.sup. 0 9 0.02 + benfuracarb 0.5 + 2.5 14 33 0.06 Compound 44 +
imidacloprid 0.5 + 1.sup. 0 3 0.03 + benfuracarb 0.5 + 2.5 18 53
0.08 Compound 45 + imidacloprid 0.5 + 1.sup. 0 4 0.02 + benfuracarb
0.5 + 2.5 25 23 0.08 Compound 46 + imidacloprid 0.5 + 1.sup. 0 7
0.05 + benfuracarb 0.5 + 2.5 13 54 0.09 Compound 47 + imidacloprid
0.5 + 1.sup. 0 7 0.04 + benfuracarb 0.5 + 2.5 16 36 0.08 Compound
48 + imidacloprid 0.5 + 1.sup. 0 6 0.03 + benfuracarb 0.5 + 2.5 33
28 0.08 Compound 54 + imidacloprid 0.5 + 1.sup. 0 9 0.02 +
benfuracarb 0.5 + 2.5 31 45 0.07 Compound 129 + imidacloprid 0.5 +
1.sup. 0 7 0.04 + benfuracarb 0.5 + 2.5 15 57 0.08 Compound 130 +
imidacloprid 0.5 + 1.sup. 0 6 0.06 + benfuracarb 0.5 + 2.5 18 61
0.09 Compound 131 + imidacloprid 0.5 + 1.sup. 0 8 0.05 +
benfuracarb 0.5 + 2.5 20 49 0.08 Compound 19 0.5 325 389 0.16
Compound 20 0.5 315 354 0.15 Compound 39 0.5 343 372 0.25 Compound
40 0.5 322 358 0.33 Compound 41 0.5 333 385 0.35 Compound 42 0.5
345 389 0.22 Compound 43 0.5 309 334 0.17 Compound 44 0.5 323 358
0.24 Compound 45 0.5 353 395 0.13 Compound 46 0.5 349 387 0.18
Compound 47 0.5 328 365 0.11 Compound 48 0.5 345 383 0.33 Compound
54 0.5 328 334 0.25 Compound 129 0.5 323 390 0.13 Compound 130 0.5
331 382 0.16 Compound 131 0.5 342 391 0.14 imidacloprid 1 0 29 1.63
benfuracarb 2.5 78 244 1.13 Untreated plot -- 355 388 1.54
Test Example 8
Test for the Control of Diamondback Moth (Plutella xyloxtella) and
Aphid on Cabbage by Soil Treatment
[0114] A granular preparation was mixed into bed soil, and the
mixture was filled into a cell seedling box and sown with seeds of
cabbage (variety: YR Seitoku). Otherwise, cell seedling planted
cabbage was treated with the granular agent either by a treatment
in the foliage leaf extraction period, or by a pre-transplanting
treatment, or by a pricking-in hole treatment, or by a plant foot
treatment after the planting. Twenty one days after the
transplanting (in the middle of June), the number of parasitic
insects was counted on 30 hills in the case of diamondback moth and
on 10 hills in the case of aphid.
[0115] The results are shown in Table 9.
TABLE-US-00020 TABLE 9 Number of parasitic insects Dosage per 30
hills (mg ai/ Method of Diamond- Test agent hill) treatment back
moth Aphid Compound + imidacloprid 5 + 20 pre- 0 0 19 transplanting
treatment 5 + 20 pricking-in 0 0 hole treatment 5 + 20 plant foot 0
0 treatment Compound + imidacloprid 5 + 20 pre- 0 0 20
transplanting treatment 5 + 20 pricking-in 0 0 hole treatment 5 +
20 plant foot 0 0 treatment Compound + imidacloprid 5 + 20 pre- 0 0
39 transplanting treatment 5 + 20 pricking-in 0 0 hole treatment 5
+ 20 plant foot 0 0 treatment Compound + imidacloprid 5 + 20 pre- 0
0 40 transplanting treatment 5 + 20 pricking-in 0 0 hole treatment
5 + 20 plant foot 0 0 treatment Compound + imidacloprid 5 + 20 pre-
0 0 41 transplanting treatment 5 + 20 pricking-in 0 0 hole
treatment 5 + 20 plant foot 0 0 treatment Compound + imidacloprid 5
+ 20 pre- 0 0 42 transplanting treatment 5 + 20 pricking-in 0 0
hole treatment 5 + 20 plant foot 0 0 treatment Compound +
imidacloprid 5 + 20 pre- 0 0 43 transplanting treatment 5 + 20
pricking-in 0 0 hole treatment 5 + 20 plant foot 0 0 treatment
Compound + imidacloprid 5 + 20 pre- 0 0 44 transplanting treatment
5 + 20 pricking-in 0 0 hole treatment 5 + 20 plant foot 0 0
treatment Compound + imidacloprid 5 + 20 pre- 0 0 45 transplanting
treatment 5 + 20 pricking-in 0 0 hole treatment 5 + 20 plant foot 0
0 treatment Compound + imidacloprid 5 + 20 pre- 0 0 46
transplanting treatment 5 + 20 pricking-in 0 0 hole treatment 5 +
20 plant foot 0 0 treatment Compound + imidacloprid 5 + 20 pre- 0 0
47 transplanting treatment 5 + 20 pricking-in 0 0 hole treatment 5
+ 20 plant foot 0 0 treatment Compound + imidacloprid 5 + 20 pre- 0
0 48 transplanting treatment 5 + 20 pricking-in 0 0 hole treatment
5 + 20 plant foot 0 0 treatment Compound + imidacloprid 5 + 20 pre-
0 0 54 transplanting treatment 5 + 20 pricking-in 0 0 hole
treatment 5 + 20 plant foot 0 0 treatment Compound + imidacloprid 5
+ 20 pre- 0 0 129 transplanting treatment 5 + 20 pricking-in 0 0
hole treatment 5 + 20 plant foot 0 0 treatment Compound +
imidacloprid 5 + 20 pre- 0 0 130 transplanting treatment 5 + 20
pricking-in 0 0 hole treatment 5 + 20 plant foot 0 0 treatment
Compound + imidacloprid 5 + 20 pre- 0 0 131 transplanting treatment
5 + 20 pricking-in 0 0 hole treatment 5 + 20 plant foot 0 0
treatment Compound 5 soil 1 445 19 incorporation 5 true leaf 2 457
extraction season treatment 5 pre- 1 399 transplanting treatment 5
pricking-in 1 467 hole treatment 5 plant foot 2 489 treatment
Compound 5 soil 4 512 20 incorporation 5 true leaf 2 498 extraction
season treatment 5 pre- 6 478 transplanting treatment 5 pricking-in
3 499 hole treatment 5 plant foot 5 501 treatment Compound 5 soil 3
513 39 incorporation 5 true leaf 2 487 extraction season treatment
5 pre- 4 457 transplanting treatment 5 pricking-in 3 437 hole
treatment 5 plant foot 2 456 treatment Compound 5 soil 2 472 40
incorporation 5 true leaf 1 510 extraction season treatment 5 pre-
1 477 transplanting treatment 5 pricking-in 1 486 hole treatment 5
plant foot 3 478 treatment Compound 5 soil 3 457 41 incorporation 5
true leaf 2 495 extraction season treatment 5 pre- 1 458
transplanting treatment 5 pricking-in 2 511 hole treatment 5 plant
foot 2 456 treatment Compound 5 soil 3 475 42 incorporation 5 true
leaf 2 485 extraction season treatment 5 pre- 3 435 transplanting
treatment 5 pricking-in 1 473 hole treatment 5 plant foot 3 498
treatment Compound 5 soil 2 501 43 incorporation 5 true leaf 2 448
extraction season treatment 5 pre- 3 482 transplanting treatment 5
pricking-in 1 447 hole treatment 5 plant foot 2 467 treatment
Compound 5 soil 3 449 44 incorporation 5 true leaf 2 502 extraction
season treatment 5 pre- 3 498 transplanting treatment 5 pricking-in
3 478 hole treatment 5 plant foot 2 492 treatment Compound 5 soil 2
472 45 incorporation 5 true leaf 2 463 extraction season treatment
5 pre- 1 472 transplanting treatment 5 pricking-in 5 465 hole
treatment 5 plant foot 4 489 treatment Compound 5 soil 1 505 46
incorporation 5 true leaf 3 498 extraction season treatment 5 pre-
1 479 transplanting treatment 5 pricking-in 3 447 hole treatment 5
plant foot 2 469 treatment
Compound 5 soil 3 438 47 incorporation 5 true leaf 2 499 extraction
season treatment 5 pre- 4 452 transplanting treatment 5 pricking-in
1 477 hole treatment 5 plant foot 2 511 treatment Compound 5 soil 5
502 48 incorporation 5 true leaf 2 442 extraction season treatment
5 pre- 5 476 transplanting treatment 5 pricking-in 1 492 hole
treatment 5 plant foot 4 456 treatment Compound 5 soil 1 478 54
incorporation 5 true leaf 3 459 extraction season treatment 5 pre-
1 487 transplanting treatment 5 pricking-in 3 499 hole treatment 5
plant foot 2 463 treatment Compound 5 soil 2 455 129 incorporation
5 true leaf 1 458 extraction season treatment 5 pre- 2 402
transplanting treatment 5 pricking-in 3 397 hole treatment 5 plant
foot 1 481 treatment Compound 5 soil 1 453 130 incorporation 5 true
leaf 1 399 extraction season treatment 5 pre- 1 421 transplanting
treatment 5 pricking-in 2 467 hole treatment 5 plant foot 1 498
treatment Compound 5 soil 1 432 131 incorporation 5 true leaf 1 465
extraction season treatment 5 pre- 2 428 transplanting treatment 5
pricking-in 2 391 hole treatment 5 plant foot 1 486 treatment
imidacloprid 20 pre- 35 10 transplanting treatment 20 picking-in 40
16 hole treatment 20 plant foot 38 13 treatment Untreated -- 41 479
plot Note: The effect in soil incorporation and true leaf
extraction season treatment could not be evaluated due to
phytotoxicity, in cases of a single use of imidacloprid and a mixed
use of imidacloprid.
Test Example 9
Test for the Effect Against Cutworm on Beet
[0116] Beet seedlings (variety: Monoace S) planted in a paper pot
was treated with 3 L/m.sup.2 of a solution of an agent diluted to a
predetermined concentration, by the method of drench. Just after
the drench, the plant was set. Predetermined days after the
setting, the number of injured hills per 100 hills was counted. The
test was carried out with two replications, 80 m.sup.2 per one
plot.
[0117] The results are shown in Table 10.
TABLE-US-00021 TABLE 10 Number of injured hills per 100 hills
Dosage After After After (g ai/ 60 90 120 Test agents 10a) days
days days Compound 19 + acephate 15 + 50 0 3 11 Compound 20 +
acephate 15 + 50 0 4 10 Compound 39 + acephate 15 + 50 0 2 8
Compound 40 + acephate 15 + 50 0 1 7 Compound 41 + acephate 15 + 50
0 5 9 Compound 42 + acephate 15 + 50 0 4 10 Compound 43 + acephate
15 + 50 0 2 6 Compound 44 + acephate 15 + 50 0 3 8 Compound 45 +
acephate 15 + 50 0 1 5 Compound 46 + acephate 15 + 50 0 4 11
Compound 47 + acephate 15 + 50 0 5 12 Compound 48 + acephate 15 +
50 0 2 5 Compound 54 + acephate 15 + 50 0 2 6 Compound 129 +
acephate 15 + 50 0 3 14 Compound 130 + acephate 15 + 50 0 2 9
Compound 131 + acephate 15 + 50 0 5 12 Compound 19 15 0 8 21
Compound 20 15 0 7 20 Compound 39 15 0 6 17 Compound 40 15 0 9 23
Compound 41 15 0 7 21 Compound 42 15 0 8 22 Compound 43 15 0 6 19
Compound 44 15 0 7 20 Compound 45 15 0 9 23 Compound 46 15 0 8 20
Compound 47 15 0 9 21 Compound 48 15 0 7 18 Compound 54 15 0 8 19
Compound 129 15 0 10 22 Compound 130 15 0 7 19 Compound 131 15 0 8
21 acephate 50 2 14 24 Untreated plot -- 6 26 30
Test Example 10
Test for the Control of Citrus Yellow Thrips (Frankliniella
occidentalis) on Egg Plant by the Combined Use with Natural Enemy
Pesticide
[0118] An agent solution diluted to a predetermined concentration
was sprayed by means of a shouldered spraying machine to citrus
yellow thrips (Frankliniella occidentalis) parasitic on egg-plant
(variety: Senryo No. 2) in a vinyl house. After air-dryness, 100
heads per hill of Amblyseius cucumeris were let inoculate. Fourteen
days, twenty one days and twenty eight days after the treatment,
the numbers of citrus yellow thrips and Amblyseius cucumeris were
counted on twenty leaves showing a most serious injury (the first
ten days of June).
[0119] The results are shown in Table 11.
TABLE-US-00022 TABLE 11 Amount Number of parasitic applied insects
per 20 (ppm or leaves adults After After After Test agent number)
60 days 90 days 120 days Compound 19 + Amblyseius 100 ppm + 100 2 0
3 cucumeris adults/hill Compound 20 + Amblyseius 100 ppm + 100 3 0
2 cucumeris adults/hill Compound 39 + Amblyseius 100 ppm + 100 1 0
1 cucumeris adults/hill Compound 40 + Amblyseius 100 ppm + 100 4 0
4 cucumeris adults/hill Compound 41 + Amblyseius 100 ppm + 100 5 1
6 cucumeris adults/hill Compound 42 + Amblyseius 100 ppm + 100 3 0
4 cucumeris adults/hill Compound 43 + Amblyseius 100 ppm + 100 1 0
2 cucumeris adults/hill Compound 44 + Amblyseius 100 ppm + 100 1 0
1 cucumeris adults/hill Compound 45 + Amblyseius 100 ppm + 100 2 0
4 cucumeris adults/hill Compound 46 + Amblyseius 100 ppm + 100 4 1
6 cucumeris adults/hill Compound 47 + Amblyseius 100 ppm + 100 1 0
2 cucumeris adults/hill Compound 48 + Amblyseius 100 ppm + 100 3 1
5 cucumeris adults/hill Compound 54 + Amblyseius 100 ppm + 100 2 0
2 cucumeris adults/hill Compound 129 + Amblyseius 100 ppm + 100 2 0
3 cucumeris adults/hill Compound 130 + Amblyseius 100 ppm + 100 4 0
2 cucumeris adults/hill Compound 131 + Amblyseius 100 ppm + 100 3 0
4 cucumeris adults/hill Compound 19 100 ppm 20 27 55 Compound 20
100 ppm 21 28 49 Compound 39 100 ppm 19 32 58 Compound 40 100 ppm
22 31 52 Compound 41 100 ppm 18 29 59 Compound 42 100 ppm 19 25 50
Compound 43 100 ppm 23 31 57 Compound 44 100 ppm 25 33 53 Compound
45 100 ppm 18 29 59 Compound 46 100 ppm 20 34 57 Compound 47 100
ppm 21 27 52 Compound 48 100 ppm 19 31 59 Compound 54 100 ppm 18 25
61 Compound 129 100 ppm 19 29 51 Compound 130 100 ppm 21 28 50
Compound 131 100 ppm 23 30 54 Amblyseius cucumeris 100 8 5 15
adults/hill Untreated plot -- 22 32 58
Test Example 11
Test for the Control of Rice Leafroller (Cnaphalocrocis medinalis),
Rice Blast, Barnyard Grass (Echinochloa crus-Galli) and Bulrush
(Scirpus juncoides Roxb.) on Paddyfield Rice Plant by Submerged
Application to Main Paddyfield
[0120] Ten days after the transplantation (in the middle ten days
of May), a granular preparation was applied to water surface of
main paddyfield. The controlling effect on rice leafroller was
evaluated by counting the injured leaves on each plot (100 hills)
50 days after the transplantation, and calculating the percentage
of injured leaves therefrom. The effect against rice blast was
evaluated by measuring the areal rate of disease spot 60 days after
the transplantation. The effects against barnyard grass and bulrush
were evaluated by measuring the herbicidal effect by the naked eye
four weeks after the treatment and expressing the result by
numerically (0 means "no effect", and 10 means "complete
withering"). At the same time, the chemical injury on rice plant
was also evaluated (0 means "no influence").
[0121] The results are shown in Table 12.
TABLE-US-00023 TABLE 12 Percentage Areal rate of injured of disease
Herbicidal leaves (%) spot (%) effect Phyto- Test agent After After
barnyard toxicity Dosage (g ai/10a) 50 days 60 days grass fulrush
rice Compound + pyroquilon + bensulfron- 0.13 0.5 10 10 0 129
methyl + indanofan 10.0 + 150.0 + 5.0 + 15.0 Compound + fenoxanyl +
bensulfron- 0.12 0.4 10 10 0 129 methyl + indanofan 10.0 + 250.0 +
5.0 + 15.0 Compound + pyroquilon + bensulfron- 0.11 0.3 10 10 0 130
methyl + indanofan 10.0 + 150.0 + 5.0 + 15.0 Compound + fenoxanyl +
bensulfron- 0.15 0.5 10 10 0 130 methyl + indanofan 10.0 + 250.0 +
5.0 + 15.0 Compound + pyroquilon + bensulfron- 0.13 0.3 10 10 0 131
methyl + indanofan 10.0 + 150.0 + 5.0 + 15.0 Compound + fenoxanyl +
bensulfron- 0.14 0.4 10 10 0 131 methyl + indanofan 10.0 + 250.0 +
5.0 + 15.0 Compound 10.0 0.15 8.1 0 0 0 129 Compound 10.0 0.13 7.9
0 0 0 130 Compound 10.0 0.16 8.3 0 0 0 131 pyroquilon + bensulfron-
1.56 0.6 10 10 0 methyl + indanofan 250.0 + 5.0 + 15.0 fenoxanyl +
bensulfron- 1.63 0.8 10 10 0 methyl + indanofan 250.0 + 5.0 + 15.0
Untreated -- 1.66 8.2 0 0 0 plot
* * * * *