U.S. patent application number 09/362087 was filed with the patent office on 2002-01-31 for fungicidal composition and method for using the same.
Invention is credited to NISHIGUCHI, TSUTOMU, TAJIMA, SOHKICHI, TAKEMOTO, TSUYOSHI, YAMAMOTO, YOSHINOBU.
Application Number | 20020013350 09/362087 |
Document ID | / |
Family ID | 16891672 |
Filed Date | 2002-01-31 |
United States Patent
Application |
20020013350 |
Kind Code |
A1 |
NISHIGUCHI, TSUTOMU ; et
al. |
January 31, 2002 |
FUNGICIDAL COMPOSITION AND METHOD FOR USING THE SAME
Abstract
The present invention relates to a fungicidal composition
obtained by mixing a 1,2,3-thiadiazole derivative of general
formula (I) useful as a plant disease controller with at least one
fungicide selected from the compounds having a fungicidal activity
against plant diseases, and to a method for using the same: 1
wherein R.sup.1 is hydrogen, alkyl or cycloalkyl and R is
CO--Y--R.sup.3, wherein Y is O, S, NR.sup.4 or the like and R.sup.3
is hydrogen, alkyl, phenyl, 5- or 6-membered heterocycle or the
like.
Inventors: |
NISHIGUCHI, TSUTOMU;
(KAWACHINAGANO-SHI, JP) ; TAKEMOTO, TSUYOSHI;
(KAWACHINAGANO-SHI, JP) ; TAJIMA, SOHKICHI;
(OSAKA-SHI, JP) ; YAMAMOTO, YOSHINOBU;
(KAWACHINAGANO-SHI, JP) |
Correspondence
Address: |
MANELLI DENISON & SELTER
2000 M STREET NW SUITE 700
WASHINGTON
DC
20036-3307
US
|
Family ID: |
16891672 |
Appl. No.: |
09/362087 |
Filed: |
July 28, 1999 |
Current U.S.
Class: |
514/354 ;
514/361; 514/760 |
Current CPC
Class: |
A01N 43/82 20130101;
A01N 43/82 20130101; A01N 61/00 20130101; A01N 59/20 20130101; A01N
47/38 20130101; A01N 43/90 20130101; A01N 43/653 20130101; A01N
43/54 20130101; A01N 43/28 20130101; A01N 43/82 20130101; A01N
2300/00 20130101 |
Class at
Publication: |
514/354 ;
514/760; 514/361 |
International
Class: |
A01N 043/54; A01N
043/40; A01N 043/82; A01N 029/02 |
Foreign Application Data
Date |
Code |
Application Number |
Jul 30, 1998 |
JP |
10-229403 |
Claims
What is claimed is:
1. A fungicidal composition comprising, as active ingredients
thereof, a 1,2,3-thiadiazole derivative represented by the general
formula (I) and at least one compound selected from the compounds
having a fungicidal activity against plant diseases: 7wherein
R.sup.1 represents hydrogen atom, (C.sub.1-6) alkyl group or
(C.sub.3-7) cycloalkyl group; and R.sup.2 represents a group of the
formula: CO--Y--R.sup.3 wherein R.sup.3 represents hydrogen atom,
(C.sub.1-20) alkyl group, halo (C.sub.1-20) alkyl group,
(C.sub.2-20) alkenyl group, halo ((C.sub.2-20) alkenyl group,
(C.sub.2-20)alkynyl group, halo (C.sub.2-20) alkynyl group,
(C.sub.3-12) cyclalky group, (C.sub.1-6) alkoxy (C.sub.1-6) alkyl
group, (C.sub.1-6) alkoxy (C.sub.1-6) alkoxy (C.sub.1-6) alkyl
group, carboxyl (C.sub.1-6) alkyl group, (C.sub.1-6) alkoxycarbonyl
(C.sub.1-6) alkyl group, carbamoyl (C.sub.1-6) alkyl group,
substituted carbamoyl (C.sub.1-6) alkyl group having 1 or 2, same
or different substituents selected from the group consisting of
(C.sub.1-6) alkyl group, phenyl group and substituted phenyl group
substituted with at least one same or different halogen atom or
(C.sub.1-6) alkyl group, cyano (C.sub.1-6) alkyl group, (C.sub.1-6)
alkylcarbonyloxy (C.sub.1-6) alkyl group, (C.sub.1-6)
alkylcarbonylamino (C.sub.1-6) alkyl group, phenyl group,
substituted phenyl group having 1 to 5, same or different
substituents selected from the group consisting of halogen atom,
hydroxyl group, cyano group, nitro group, (C.sub.1-6) alkyl group,
halo (C.sub.1-6) alkyl group, (C.sub.1-6) alkoxy group, halo
(C.sub.1-6) alkoxy group, carboxyl group, (C.sub.1-12)
alkoxycarbonyl group, carbamoyl group and substituted carbamoyl
group having 1 or 2, same or different substituents selected from
the group consisting of halogen atom, (C.sub.1-12) alkyl group,
phenyl group and substituted phenyl group substituted with 1 to 5,
same or different (C.sub.1-6) alkyl groups, phenyl (C.sub.1-6)
alkyl group, substituted phenyl (C.sub.1-6) alkyl group having, on
the ring thereof, 1 to 5, same or different substituents selected
from the group consisting of halogen atom, hydroxyl group, cyano
group, nitro group, (C.sub.1-6) alkyl group, halo (C.sub.1-6) alkyl
group, (C.sub.1-6) alkoxy group, halo (C.sub.1-6) alkoxy group,
carboxyl group, (C.sub.1-12) alkoxycarbonyl group, carbamoyl group
and substituted carbamoyl group having 1 or 2, same or different
substituent selected from the group consisting of halogen atom,
(C.sub.1-12) alkyl group, phenyl group and substituted phenyl group
substituted with 1 to 5, same or different (C.sub.1-6) alkyl
groups, phenylcarbonyloxy (C.sub.1-6) alkyl group, substituted
phenylcarbonyloxy (C.sub.1-6) alkyl group having, on the ring
thereof, 1 to 5, same or different substituents selected from the
group consisting of halogen atom, hydroxyl group, cyano group,
nitro group, (C.sub.1-6) alkyl group, halo (C.sub.1-6) alkyl group,
(C.sub.1-6) alkoxy group, halo (C.sub.1-6) alkoxy group, carboxyl
group, (C.sub.1-6) alkoxycarbonyl group, carbamoyl group and
substituted carbamoyl group having 1 or 2, same or different
substituents selected from the group consisting of halogen atom,
(C.sub.1-6) alkyl group, phenyl group and substituted phenyl group
substituted with 1 to 5, same or different (C.sub.1-6) alkyl
groups, phenylcarbonyl (C.sub.1-6) aminoalkyl group, substituted
phenylcarbonyl (C.sub.1-6) aminoalkyl group having, on the ring
thereof, 1 to 5, same or different substituents selected from the
group consisting of halogen atom, hydroxyl group, cyano group,
nitro group, (C.sub.1-6) alkyl group, halo (C.sub.1-6) alkyl group,
(C.sub.1-6) alkoxy group, halo (C.sub.16) alkoxy group, carboxyl
group, (C.sub.1-12) alkoxycarbonyl group, carbamoyl group and
substituted carbamoyl group having 1 or 2, same or different
substituents selected from the group consisting of halogen atom,
(C.sub.1-12) alkyl group, phenyl group and substituted phenyl group
substituted with 1 to 5, same or different (C.sub.1-6) alkyl
groups, 5- or 6-membered heterocycle having at least one same or
different heteroatoms selected from the group consisting of oxygen
atom, sulfur atom and nitrogen atom, substituted 5-or 6-membered
heterocycle having 1 to 5 same or different substituents selected
from the group consisting of halogen atom, hydroxyl group, cyano
group, nitro group, (C.sub.1-6) alkyl group, halo (C.sub.1-6) alkyl
group, (C.sub.1-6) alkoxy group, halo (C.sub.1-6) alkoxy group,
carboxyl group, (C.sub.1-12) alkoxycarbonyl group, carbamoyl group
and substituted carbamoyl group having 1 or 2, same or different
substituents selected from the group consisting of halogen atom,
(C.sub.1-12) alkyl group, phenyl group and substituted phenyl group
substituted with 1 to 5, same or different (C.sub.1-6) alkyl
groups, 5- or 6-membered heterocycle (C.sub.1-6) alkyl group having
at least one same or different heteroatoms selected from the group
consisting of oxygen atom, sulfur atom and nitrogen atom,
substituted 5- or 6-membered heterocycle (C.sub.1-6) alkyl group
having 1 to 5, same or different substituents selected from the
group consisting of halogen atom, hydroxyl group, cyano group,
nitro group, (C.sub.1-6) alkyl group, halo (C.sub.1-6) alkyl group,
(C.sub.1-6) alkoxy group, halo (C.sub.1-6) alkoxygroup, carboxyl
group, (C.sub.1-12) alkoxycarbonyl group, carbamoyl group and
substituted carbamoyl group having 1 or 2, same or different
substituents selected from the group consisting of halogen atom,
(C.sub.1-12) alkyl group, phenyl group and substituted phenyl group
substituted with 1 to 5, same or different (C.sub.1-6) alkyl
groups, 5- or 6-membered heterocycle carbonyloxy v alkyl group
having at least one, same or different heteroatoms selected from
the group consisting of oxygen atom, sulfur atom and nitrogen atom,
substituted 5- or 6-membered heterocycle carbonyloxy (C.sub.1-6)
alkyl group having 1 to 5, same or different substituents selected
from the group consisting of halogen atom, hydroxyl group, cyano
group, nitro group, (C.sub.1-6) alkyl group, halo (C.sub.1-6) alkyl
group, (C.sub.1-6) alkoxy group, halo (C.sub.1-6) alkoxy group,
carboxyl group, (C.sub.1-12) alkoxycarbonyl group, carbamoyl group
and substituted carbamoyl group having 1 or 2, same or different
substituents selected from the group consisting of halogen atom,
(C.sub.1-12) alkyl group, phenyl group and substituted phenyl group
substituted with 1 to 5, same or different (C.sub.1-6) alkyl
groups, 5- or 6-membered heterocycle carbonylamino (C.sub.1-6)
alkyl group having at least one same or different heteroatoms
selected from the group consisting of oxygen atom, sulfur atom and
nitrogen atom, substituted 5-or 6-membered heterocycle
carbonylamino (C.sub.1-6) alkyl group having 1 to 5, same or
different substituents selected from the group consisting of
halogen atom, hydroxyl group, cyano group, nitro group, (C.sub.1-6)
alkyl group, halo (C.sub.1-6) alkyl group, (C.sub.1-6) alkoxy
group, halo (C.sub.1-6) alkoxy group, carboxyl group, (C.sub.1-12)
alkoxycarbonyl group, carbamoyl group and substituted carbamoyl
group substituted with 1 or 2, same or different substituents
selected from halogen atom, (C.sub.1-12) alkyl group, phenyl group
and substituted phenyl group substituted with 1 to 5, same or
different (C.sub.1-6) alkyl groups, or a group of the formula:
--N=C (R.sup.5)R.sup.6 wherein R.sup.5 and R.sup.6, same or
different each other, represent hydrogen atom, (C.sub.1-6) alkyl
group, halo (C.sub.1-6) alkyl group, (C.sub.1-6) cycloalkyl group,
phenyl group or substituted phenyl group substituted with same or
different substituents selected from the group consisting of
halogen atom, (C.sub.1-6) alkyl group and (C.sub.1-6) alkoxy group,
or R.sup.5 and R.sup.6 may also be taken conjointly to represent
(C.sub.2-6) alkylene group which may be intercepted by O, S or
NR.sup.4 in which R.sup.4 is hydrogen atom or (C.sub.1-6) alkyl
group; and Y represents O, S or NR.sup.4 in which R.sup.4is as
defined above, or a group of the formula: 8wherein X, same or
different, represents halogen atom, hydroxyl group, cyano group,
nitro group, (C.sub.1-6) alkyl group, halo (C.sub.1-6) alkyl group,
(C.sub.1-6) alkoxy group, halo (C.sub.1-6) alkoxy group,
(C.sub.1-6) alkylcarbonyl group, carboxyl group, (C.sub.1-12)
alkoxycarbonyl group, carbamoyl group and substituted carbamoyl
group having 1 or 2 same or different substituents selected from
the group consisting of halogen atom, (C.sub.1-12) alkyl group,
phenyl group and substituted phenyl group substituted with 1 to 5,
same or different (C.sub.1-6) alkyl groups; and n represents an
integer of 0 to 4.
2. A method for using a fungicidal composition which comprises
applying an effective quantity of the fungicidal composition
according to claim 1 to an objective plant for the purpose of
controlling an undesirable plant disease.
3. A method for using a fungicidal composition which comprises
applying an effective quantity of the fungicidal composition
according to claim 1 to seed of an objective plant or to the
cultivation carrier to be sown with seed of an objective plant for
the purpose of controlling an undesirable plant disease.
4. A method for using the fungicidal composition according to claim
3, wherein said objective plant is a cereal, a fruit plant or a
vegetable.
Description
BACKGROUND OF THE INVENTION
[0001] 1. Field of the Invention
[0002] The present invention relates to a fungicidal composition
obtained by mixing a 1,2,3-thiadiazole derivative represented by
general formula (I) useful as a plant disease controller with at
least one fungicides selected from the compounds having a
fungicidal activity against plant diseases, and a method for using
the same.
[0003] 2. Related Art
[0004] Although some of the 1,2,3-thiadiazole derivatives
represented by the general formula (I) are novel compounds, many of
such derivatives are disclosed in JP-A 8-325110 which mentions
usefulness of these compounds as a plant disease controller. On the
other hand, the compounds constituting the other ingredient of the
composition of the present invention which are compounds having a
fungicidal activity against plant diseases are known fungicides
disclosed in literature.
SUMMARY OF THE INVENTION
[0005] With the aim of further decreasing the dosage of
1,2,3-thiadiazole derivatives, the present inventors attempted a
combined use of the 1,2,3-thiadiazole derivatives with a variety of
known fungicides. As a result, it was found that an effect
unexpectable from their single use could be exhibited by such a
combined use. Based on this finding, the present invention was
accomplished.
[0006] It was further found that an excellent effect unexpectable
from foliage treatment could be exhibited by treating the seeds or
the cultivation carrier used for seeding with a combination of a
1,2, 3-thiadiazole derivative and other fungicides. Based on this
finding, the present invention was accomplished.
DETAILED DESCRIPTION OF THE INVENTION
[0007] The present invention relates to a fungicidal composition
comprising, as active ingredients thereof, a 1,2,3-thiadiazole
derivative represented by the following general formula (I) and at
least one compound selected from the compounds having a fungicidal
activity against plant diseases, and to a method for using the
same: 2
[0008] wherein R.sup.1 represents hydrogen atom, (C.sub.1-6) alkyl
group or (C.sub.3-7) cycloalkyl group; and
[0009] R.sup.2 represents a group of the formula:
CO--Y--R.sup.3
[0010] wherein R.sup.3 represents hydrogen atom, (C.sub.1-20) alkyl
group, halo (C.sub.1-20) alkyl group, (C.sub.2-20) alkenyl group,
halo (C.sub.2-20) alkenyl group, (C.sub.2-20) alkynyl group, halo
(C.sub.2-20) alkynyl group, (C.sub.3-12) cycloalkyl group,
(C.sub.1-6) alkoxy (C.sub.1-6) alkyl group, (C.sub.1-6) alkoxy
(C.sub.1-6)alkoxy (C.sub.1-6) alkyl group, carboxyl (C.sub.1-6))
alkyl group, (C.sub.1-20) alkoxycarbonyl (C.sub.1-6) alkyl group,
carbamoyl (C1-6) alkyl group, substituted carbamoyl (C.sub.1-6)
alkyl group having 1 or 2, same or different substituents selected
from the group consisting of (C.sub.1-6) alkyl group, phenyl group
and substituted phenyl group substituted with at least one same or
different halogen atom or (C.sub.1-6) alkyl group, cyano
(C.sub.1-6) alkyl group, (C.sub.1-6) alkylcarbonyloxy (C.sub.1-6)
alkyl group, (C.sub.1-6) alkylcarbonylamino (C1-6) alkyl group,
phenyl group, substituted phenyl group having 1 to 5, same or
different substituents selected from the group consisting of
halogen atom, hydroxyl group, cyano group, nitro group, (C1-6)
alkyl group, halo (C.sub.1-6) alkyl group, (C.sub.1-6) alkoxy
group, halo (C1-6) alkoxy group, carboxyl group, (C.sub.1-12)
alkoxycarbonyl group, carbamoyl group and substituted carbamoyl
group having 1 or 2, same or different substituents selected from
the group consisting of halogen atom, (C.sub.1-12) alkyl group,
phenyl group and substituted phenyl group substituted with 1 to 5,
same or different (C.sub.1-6) alkyl groups, phenyl (C.sub.1-6)
alkyl group, substituted phenyl (C.sub.1-6) alkyl group having, on
the ring thereof, 1 to 5, same or different substituents selected
from the group consisting of halogen atom, hydroxyl group, cyano
group, nitro group, (C.sub.1-6) alkyl group, halo (C.sub.1-6) alkyl
group, (C.sub.1-6) alkoxy group, halo (C.sub.1-6) alkoxy group,
carboxyl group, (C.sub.1-12) alkoxycarbonyl group, carbamoyl group
and substituted carbamoyl group having 1 or 2, same or different
substituent selected from the group consisting of halogen atom,
(C1-12) alkyl group, phenyl group and substituted phenyl group
substituted with 1 to 5, same or different (C.sub.1-6) alkyl
groups, phenylcarbonyloxy (C.sub.1-6) alkyl group, substituted
phenylcarbonyloxy (C.sub.1-6) alkyl group having, on the ring
thereof, 1 to 5, same or different substituents selected from the
group consisting of halogen atom, hydroxyl group, cyano group,
nitro group, (C.sub.1-6) alkyl group, halo (C1-6) alkyl group,
(C.sub.1-6) alkoxy group, halo (C.sub.1-6) alkoxy group, carboxyl
group, (C1-12) alkoxycarbonyl group, carbamoyl group and
substituted carbamoyl group having 1 or 2, same or different
substituents selected from the group consisting of halogen atom,
(C.sub.1-12) alkyl group, phenyl group and substituted phenyl group
substituted with 1 to 5, same or different (C.sub.1-6) alkyl
groups, phenylcarbonyl (C.sub.1-6) aminoalkyl group, substituted
phenylcarbonyl (C.sub.1-6) aminoalkyl group having, on the ring
thereof, 1 to 5, same or different substituents selected from the
group consisting of halogen atom, hydroxyl group, cyano group,
nitro group, (C.sub.1-6) alkyl group, halo (C.sub.1-6) alkyl group,
(C.sub.1-6) alkoxy group, halo (C.sub.1-6) alkoxy group, carboxyl
group, (C.sub.1-12) alkoxycarbonyl group, carbamoyl group and
substituted carbamoyl group having 1 or 2, same or different
substituents selected from the group consisting of halogen atom,
(C.sub.1-12) alkyl group, phenyl group and substituted phenyl group
substituted with 1 to 5, same or different (C.sub.1-6) alkyl
groups, 5- or 6-membered heterocycle having at least one same or
different heteroatoms selected from the group consisting of oxygen
atom, sulfur atom and nitrogen atom, substituted 5-or 6-membered
heterocycle having 1 to 5 same or different substituents selected
from the group consisting of halogen atom, hydroxyl group, cyano
group, nitro group, (C.sub.1-6) alkyl group, halo (C.sub.1-6) alkyl
group, (C.sub.1-6) alkoxy group, halo (C.sub.1-6) alkoxy group,
carboxyl group, (C.sub.1-12) alkoxycarbonyl group, carbamoyl group
and substituted carbamoyl group having 1 or 2, same or different
substituents selected from the group consisting of halogen atom,
(C.sub.1-12) alkyl group, phenyl group and substituted phenyl group
substituted with 1 to 5, same or different (C 16) alkyl groups, 5-
or 6-membered heterocycle (C.sub.1-6) alkyl group having at least
one same or different heteroatoms selected from the group
consisting of oxygen atom, sulfur atom and nitrogen atom,
substituted 5- or 6-membered heterocycle (C.sub.1-6) alkyl group
having 1 to 5, same or different substituents selected from the
group consisting of halogen atom, hydroxyl group, cyano group,
nitro group, (C.sub.1-6) alkyl group, halo (C.sub.1-6) alkyl group,
(C.sub.1-6) alkoxy group, halo (C.sub.1-6) alkoxygroup, carboxyl
group, (C.sub.1-12) alkoxycarbonyl group, carbamoyl group and
substituted carbamoyl group having 1 or 2, same or different
substituents selected from the group consisting of halogen atom,
(C.sub.1-12) alkyl group, phenyl group and substituted phenyl group
substituted with 1 to 5, same or different (C.sub.1-6) alkyl
groups, 5- or 6-membered heterocycle carbonyloxy (C.sub.1-6) alkyl
group having at least one, same or different heteroatoms selected
from the group consisting of oxygen atom, sulfur atom and nitrogen
atom, substituted 5- or 6-membered heterocycle carbonyloxy
(C.sub.1-6) alkyl group having 1 to 5, same or different
substituents selected from the group consisting of halogen atom,
hydroxyl group, cyano group, nitro group, (C.sub.1-6) (C.sub.1-6)
alkyl group, halo (C.sub.1-6) alkyl group, ((C.sub.1-6) (C.sub.1-6)
(C.sub.1-6)v alkoxy group, halo (C.sub.1-6) alkoxy group, carboxyl
group, (C.sub.1-12) alkoxycarbonyl group, carbamoyl group and
substituted carbamoyl group having 1 or 2, same or different
substituents selected from the group consisting of halogen atom,
(C.sub.1-12) alkyl group, phenyl group and substituted phenyl group
substituted with 1 to 5, same or different (C.sub.1-6) alkyl
groups, 5- or 6-membered heterocycle carbonylamino (C.sub.1-6)
alkyl group having at least one same or different heteroatoms
selected from the group consisting of oxygen atom, sulfur atom and
nitrogen atom, substituted 5-or 6-membered heterocycle
carbonylamino (C.sub.1-6) alkyl group having 1 to 5, same or
different substituents selected from the group consisting of
halogen atom, hydroxyl group, cyano group, nitro group, (C.sub.16)
alkyl group, halo (C.sub.1-6)v alkyl group, (C.sub.1-6) alkoxy
group, halo (C.sub.1-6) alkoxy group, carboxyl group, (C.sub.1-12)
alkoxycarbonyl group, carbamoyl group and substituted carbamoyl
group substituted with 1 or 2, same or different substituents
selected from halogen atom, (C.sub.1-12) alkyl group, phenyl group
and substituted phenyl group substituted with 1 to 5, same or
different (C.sub.1-6) alkyl groups, or
[0011] a group of the formula:
--N=C (R.sup.4)R.sup.6
[0012] wherein R.sup.5 and R.sup.6, same or different each other,
represent hydrogenatom, (C.sub.1-6) alkylgroup, halo (C.sub.1-6)
alkylgroup, (C.sub.1-6) cycloalkyl group, phenyl group or
substituted phenyl group substituted with same or different
substituents selected from the group consisting of halogen atom,
(C.sub.1-6) alkyl group and (C.sub.1-6) alkoxy group, or R.sup.5
and R.sup.6 may also be taken conjointly to represent (C.sub.2-6)
alkylene group which may be intercepted by O, S or NR.sup.4 in
which R.sup.4 is hydrogen atom or (C.sub.1-6) alkyl group; and Y
represents O, S or NR.sup.4in which R.sup.4 is as defined above,
or
[0013] a group of the formula: 3
[0014] wherein X, same or different, represents halogen atom,
hydroxyl group, cyano group, nitro group, (C.sub.1-6) alkyl group,
halo (C.sub.1-6) alkyl group, (C.sub.1-6)) alkoxy group, halo
(C.sub.1-6) alkoxy group, (C.sub.1-6) alkylcarbonyl group, carboxyl
group, (C.sub.1-6) alkoxycarbonyl group, carbamoyl group and
substituted carbamoyl group having 1 or 2 same or different
substituents selected from the group consisting of halogen atom,
(C.sub.1-12) alkyl group, phenyl group and substituted phenyl group
substituted with 1 to 5, same or different (C.sub.1-6) alkyl
groups; and n represents an integer of 0 to 4.
[0015] The present invention provides fungicidal compositions which
can be used at a low dosage of 1,2,3-thiadiazole derivative
represented by the general formula (I). These compositions have an
excellent activity as a fungicide. The present invention further
provides a more effective method for using the fungicidal
composition which comprises applying the active ingredient or the
fungicide containing the same to seeds or plants in the seedling
period. The use of said composition or said method for using the
composition makes it possible to stabilize the fungicidal effect
and to inhibit generation of agent-resistant fungi.
[0016] The 1,2,3-thiadiazole derivatives represented by the general
formula (I) constitute the other active ingredient of the
composition of the present invention, of which typical examples are
listed in Tables 1 and 3. The present invention is by no means
limited by these examples.
[0017] General formula (I-1)
1TABLE 1 (I-1) 4 No. R.sup.1 Y R.sup.3 Properties 1 H O H m.p.
107.1.degree. C. 2 H NH H m.p. 160.8.degree. C. 3 CH.sub.3 O H m.p.
188-189.5.degree. C. 4 CH.sub.3 O Na m.p. 230.degree. C.
(decomposition) 5 CH.sub.3 O CH.sub.3 nD 1.5165 (23.2.degree. C.) 6
CH.sub.3 O C.sub.2H.sub.5 nD 1.5075 (14.0.degree. C.) 7 CH.sub.3 O
n-C.sub.3H.sub.7 nD 1.4000 (12.5.degree. C.) 8 CH.sub.3 O
i-C.sub.3H.sub.7 nD 1.4400 (14.3.degree. C.) 9 CH.sub.3 O
s-C.sub.4H.sub.9 nD 1.4165 (24.2.degree. C.) 10 CH.sub.3 O
CH.sub.2CH(C.sub.2H.sub.5)C.sub.4H.sub.9-n nD 1.4891 (23.1.degree.
C.) 11 CH.sub.3 O n-C.sub.8H.sub.17 nD 1.4900 (12.9.degree. C.) 12
CH.sub.3 O n-C.sub.12H.sub.25 nD 1.5403 (22.0.degree. C.) 13
CH.sub.3 O n-C.sub.16H.sub.33 nD 1.4859 (22.0.degree. C.) 14
CH.sub.3 O c-C.sub.6H.sub.11 nD 1.5248 (25.2.degree. C.) 15
CH.sub.3 O CH.sub.2--Ph nD 1.5735 (13.1.degree. C.) 16 CH.sub.3 O
CH.sub.2-(4-Cl--Ph) m.p. 85.degree. C. 17 CH.sub.3 O
CH.sub.2-(3,5-Cl.sub.2--Ph) m.p. 81.degree. C. 18 CH.sub.3 O
CH.sub.2-(4-t-C.sub.4H.sub.9--Ph) nD 1.5558 (26.3.degree. C.) 19
CH.sub.3 O CH.sub.2-(4-NO.sub.2--Ph) m.p. 100.degree. C. 20
CH.sub.3 O CH(CH.sub.3)--Ph nD 1.5631 (25.0.degree. C.) 21 CH.sub.3
O Ph nD 1.5845 (20.6.degree. C.) 22 CH.sub.3 O 4-Cl--Ph m.p.
77-80.degree. C. 23 CH.sub.3 O 2-CH.sub.3--Ph m.p. 62-64.degree. C.
24 CH.sub.3 O 4-CH.sub.3--Ph m.p. 31.degree. C. 25 CH.sub.3 O
4-CH.sub.3O--Ph m.p. 73.degree. C. 26 CH.sub.3 O 2-COCH.sub.3 m.p.
77.degree. C. 27 CH.sub.3 O 2-COOCH.sub.3--Ph m.p. 102.degree. C.
28 CH.sub.3 O 2-COOC.sub.3H.sub.7-i Paste 29 CH.sub.3 O
CH.sub.2--Q.sup.1 nD 1.5391 (17.1.degree. C.) 30 CH.sub.3 O
CH.sub.2CH.sub.2O--Q.sup.2 m.p. 54.degree. C. 31 CH.sub.3 O
CH.sub.2CH(CH.sub.3)O--Q.sub.2 nD 1.5812 (22.degree. C.) 32
CH.sub.3 O (s)-CH(CH.sub.3)COOC.sub.2H.s- ub.5 nD 1.4858
(21.9.degree. C.) 33 CH.sub.3 O CH.sub.2CH.sub.2NHCO--Ph m.p.
85.degree. C. 34 CH.sub.3 O N.dbd.CH--Ph m.p. 113.5.degree. C. 35
CH.sub.3 O N.dbd.C(CH.sub.3)Ph m.p. 99.9.degree. C. 36 CH.sub.3 S
CH.sub.3 m.p. 40.1.degree. C. 37 CH.sub.3 S C.sub.2H.sub.5 nD
1.5229 (20.8.degree. C.) 38 CH.sub.3 S i-C.sub.3H.sub.7 nD 1.5620
(21.8.degree. C.) 39 CH.sub.3 S n-C.sub.12H.sub.25 nD 1.5621
(18.6.degree. C.) 40 CH.sub.3 S CH.sub.2--Ph nD 1.6239
(21.1.degree. C.) 41 CH.sub.3 NH H m.p. 115.degree. C. 42 CH.sub.3
NH CH.sub.3 m.p. 45.degree. C. 43 CH.sub.3 NH C.sub.2H.sub.5 m.p.
44.degree. C. 44 CH.sub.3 NH i-C.sub.3H.sub.7 m.p. 65.degree. C. 45
CH.sub.3 NH c-C.sub.6H.sub.11 m.p. 98.degree. C. 46 CH.sub.3 NH Ph
m.p. 110.degree. C. 47 CH.sub.3 NH 2-Cl--Ph m.p. 101.degree. C. 48
CH.sub.3 NH 3-Cl--Ph m.p. 136-142.degree. C. 49 CH.sub.3 NH
4-Cl--Ph m.p. 114.degree. C. 50 CH.sub.3 NH 2-CH.sub.3--Ph m.p.
115.degree. C. 51 CH.sub.3 NH 3-CH.sub.3--Ph m.p. 111.degree. C. 52
CH.sub.3 NH 4-CH.sub.3--Ph m.p. 109.degree. C. 53 CH.sub.3 NH
2,4-Cl.sub.2--Ph m.p. 118-119.degree. C. 54 CH.sub.3 NH
3,4-Cl.sub.2--Ph m.p. 138-139.degree. C. 55 CH.sub.3 NH
3-Cl-4-CH.sub.3--Ph m.p. 113.degree. C. 56 CH.sub.3 NH
3,4-(CH.sub.3).sub.2--Ph m.p. 111.degree. C. 57 CH.sub.3 NH
4-CH.sub.3O--Ph m.p. 117.degree. C. 58 CH.sub.3 NH 4-NO.sub.2--Ph
m.p. 175.degree. C. 59 CH.sub.3 NH 4-CN--Ph m.p. 172.degree. C. 60
CH.sub.3 NH 2-COOH--Ph m.p. 223.degree. C. 61 CH.sub.3 NH
2-COOC.sub.2H.sub.5--Ph m.p. 63.degree. C. 62 CH.sub.3 NH
4-COOCH.sub.3--Ph m.p. 133.degree. C. 63 CH.sub.3 NH
2-CONHCH.sub.3--Ph m.p. 162.degree. C. 64 CH.sub.3 NH
2-CONHC.sub.3H.sub.7-i-Ph m.p. 177.degree. C. 65 CH.sub.3 NH
3-CONHC.sub.3H.sub.7-i-Ph m.p. 158.degree. C. 66 CH.sub.3 NH
4-CON(CH.sub.3).sub.2--Ph m.p. 176.8-178.6.degree. C. 67 CH.sub.3
NH CH.sub.2--Ph m.p. 53.degree. C. 68 CH.sub.3 NH CH(CH.sub.3)
(4-Cl--Ph) m.p. 108.degree. C. 69 CH.sub.3 NH CH.sub.2CN m.p.
76-78.degree. C. 70 CH.sub.3 NH CH.sub.2CH.sub.2CN m.p.
86-87.degree. C. 71 CH.sub.3 NH CH(CH.sub.3) (i-C.sub.3H.sub.7) nD
1.5235 (25.9.degree. C.) 72 CH.sub.3 NH CH.sub.2COOC.sub.2H.sub.5
nD 1.5248 (21.5.degree. C.) 73 CH.sub.3 NH
CH.sub.2COOC.sub.8H.sub.17-n Paste 74 CH.sub.3 NH
CH.sub.2CONH(4-Cl--Ph) m.p. 211.degree. C. 75 CH.sub.3 NH
CH.sub.2CONH(4-CH.sub.3O--Ph) m.p. 188.degree. C. 76 CH.sub.3 NH
CH(CH.sub.3)CH.sub.2COOCH.sub.3 nD 1.5250 (20.4.degree. C.) 77
CH.sub.3 NH CH(i-C.sub.3H.sub.7)COOCH.sub.3 Paste 78 CH.sub.3 NH
CH(CH.sub.3)COOCH.sub.3 Paste 79 CH.sub.3 NH
CH.sub.2CH.sub.3NHCOQ.sup.2 m.p. 149.degree. C. 80 CH.sub.3 NH
N.dbd.C(CH.sub.3).sub.2 m.p. 198.degree. C. 81 CH.sub.3 NH
N.dbd.C(CH.sub.3)C.sub.2H.sub.5 m.p. 152-153.degree. C. 82 CH.sub.3
NH N.dbd.CH--Ph m.p. 238.degree. C. 83 CH.sub.3 NH
N.dbd.C(CH.sub.3)--Ph m.p. 260-270.degree. C. 84 CH.sub.3 NCH.sub.3
CH.sub.3 nD 1.5555 (13.2.degree. C.) 85 CH.sub.3 NC.sub.2H.sub.5
C.sub.2H.sub.5 nD 1.5356 (13.7.degree. C.) 86 C.sub.2H.sub.5 O H
m.p. 137.1-138.4.degree. C. 87 C.sub.2H.sub.5 O CH.sub.3 nD 1.5093
(24.1.degree. C.) 88 C.sub.2H.sub.5 O CH.sub.2--Ph nD 1.5539
(23.7.degree. C.) 89 C.sub.2H.sub.5 NH H m.p. 139.0.degree. C. 90
C.sub.2H.sub.5 NH Ph m.p. 81.9.degree. C. 91 n-C.sub.3H.sub.7 O
C.sub.2H.sub.5 nD 1.4958 (21.0.degree. C.) 92 i-C.sub.3H.sub.7 O H
m.p. 136.6.degree. C. 93 i-C.sub.3H.sub.7 O C.sub.2H.sub.5 nD
1.4943 (20.9.degree. C.) 94 i-C.sub.3H.sub.7 O n-C.sub.8H.sub.17 nD
1.4845 (21.8.degree. C.) 95 i-C.sub.3H.sub.7 O CH.sub.2--Ph nD
1.5505 (23.8.degree. C.) 96 i-C.sub.3H.sub.7 NH H m.p.
137.3.degree. C. 97 i-C.sub.3H.sub.7 NH Ph m.p. 112.3.degree. C. 98
n-C.sub.4H.sub.9 O H m.p. 92.3.degree. C. 99 n-C.sub.4H.sub.9 O
CH.sub.3 nD 1.4993 (22.3.degree. C.) 100 t-C.sub.4H.sub.9 O H m.p.
111.1.degree. C. 101 t-C.sub.4H.sub.9 O CH.sub.3 nD 1.5082
(13.0.degree. C.) 102 n-C.sub.5H.sub.11 O H m.p. 86.2.degree. C.
103 n-C.sub.5H.sub.11 O CH.sub.3 nD 1.4969 (22.5.degree. C.) 104
c-C.sub.3H.sub.5 O H m.p. 157.1.degree. C. 105 c-C.sub.3H.sub.5 O
CH.sub.3 m.p. 47.4.degree. C.
[0018] In Table 1, "Ph" represents a phenyl group, "c--" represents
an alicyclic hydrocarbon group, and Q.sup.1 and Q.sup.2 represent
the following groups, respectively: 5
[0019] Some of the compounds shown in Table 1 are in the state of a
paste, of which NMR values are shown in Table 2.
2TABLE 2 No. .sup.1H-NMR[CDCl.sub.3/TMS, .delta. value (ppm)] 73
0.88(t, 3H), 1.21-1.40(m, 10H), 1.60-1.74(m, 2H), 2.94(s, 3H),
4.18-4.24(m, 4H), 6.52(bs, 1H). 77 1.00(t, 6H), 2.30(m, 1H),
2.95(s, 3H), 3.80(s, 3H), 4.74(m, 1H), 6.42(bs, 1H). 78 1.69(s,
6H), 2.90(s, 3H), 3.81(s, 3H), 6.79(bs, 1H).
[0020]
3TABLE 3 General formula (I-2) (I-2) 6 No. R.sup.1 Xn Properties
106 CH.sub.3 H m.p. 156.degree. C. 107 CH.sub.3 5-F m.p.
176-177.degree. C. 108 CH.sub.3 6-F m.p. 151.degree. C. 109
CH.sub.3 5-CH.sub.3 m.p. 193.degree. C. 110 CH.sub.3 8-CH.sub.3
m.p. 174.degree. C. 111 C.sub.2H.sub.5 H m.p. 99.degree. C. 112
i-C.sub.3H.sub.7 H m.p. 145.degree. C.
[0021] Next, typical examples of the compounds exhibiting a
fungicidal activity against plant diseases which can be used in the
form of a mixture with the 1,2,3-thiadiazole derivatives
represented by the general formula (I) (hereinafter, these
compounds are referred to as "Compound Group I") are shown below.
The present invention is by no means limited thereby.
[0022] As the compounds exhibiting a fungicidal activity, the
following can be referred to, for instance: melanin synthesis
inhibitors (for example, the following compounds (2), (8), (7) and
(10)); strobilurins type fungicides (for example, the following
compounds (3) and (6)); ergosterol biosynthesis inhibitors (for
example, the following compounds (4), (22), (23), (24), (25), (26)
and (36)); acid amide type fungicides (for example, the following
compounds (13), (14), (15), (16) and (17)); succinic acid
synthetase inhibitor type fungicides; acylalanine type fungicides
(for example, the following compound (27)); dicarboxyimide type
fungicides (for example, the following compounds (39) and (40));
benzimidazole type fungicides (for example, the following compounds
(41), (42) and (43)); dithiocarbamate type fungicides (for example,
the following compounds (30), (31), (32) and (33));
metal-containing fungicides (for example, the following compounds
(5), (28) and (29)); antibiotics (for example, the following
compounds (9), (18) and (38)); etc.
[0023] Specific examples of the compounds exhibiting a fungicidal
activity against plant diseases which can be used as a mixed
ingredient in the composition of the present invention are listed
below:
[0024] (1) Diisopropyl-1,3-dithiolan-2-ylidene malonate (general
name: isoprothiolane)
[0025] (2) 5-Methyl-1,2,4-triazolo[3,4-b]benzothiazole (general
name: tricyclazole)
[0026] (3) Methyl
(E)-2-{2-[6-(2-cyanophenoxy)pyrimidin-4-yloxy]phenyl}-3--
methoxyacrylate (general name: azoxystrobin)
[0027] (4)
1-[2-(2,4-dichlorophenyl)-4-propyl-1,3-dioxolan-2-ylmethyl]-1H--
1,2,4-triazole (general name: propiconazole)
[0028] (5) 8-Hydroxyquinoline copper (general name:
oxine-copper)
[0029] (6) 2-Methoxyimino-N-methyl-2-(2-phenoxy)phenyl-acetamide
(code name: SSF-126)
[0030] (7)
N-[1-(4-chlorophenyl(ethyl)-2,2-dichloro-1-ethyl-3-methylcyclop-
ropanecarboxamide (general name: carpropamide)
[0031] (8) 4,5,6,7-Tetrachlorophthalide (general name:
fthalide)
[0032] (9) Kasugamycin (general name: kasugamycin)
[0033] (10) 1,2,5,6-Tetrahydropyrrolo(3,2,1-i,j)quinolin-4-one
(general name: pyroquilon)
[0034] (11) 3-Allyloxy-1,2-benzothiazole-1,1-dioxide (general name:
probenazole)
[0035] (12) S-Methylbenzo-1,2,3-thiadiazole-7-carbothiolate (code
name: CGA-245704)
[0036] (13) .alpha., .alpha.,
.alpha.-Trifluoro-3'-isopropoxy-o-toluanilid- e (general name:
flutolanil)
[0037] (14) 3'-Isopropoxy-2-methylbenzanilide (general name:
mepronil)
[0038] (15)
5-Chloro-1,3-dimethyl-N-(1,1-dimethyl-2-oxa-4-indanyl)pyrazole-
-4-carboxamide (general name: furametpyr)
[0039] (16) 1-(4-Chlorobenzyl)-1-cyclopentyl-3-phenylurea (general
name: pencycuron)
[0040] (17)
N-(2,6-Dibromo-4-trifluoromethoxyphenyl)-2-methyl-4-trifluorom-
ethylthiazole-5-carboxamide (general name: thifluzamide)
[0041] (18) Validamycin (general name: validamycin)
[0042] (19) 6-(3,5-Dichloro-4-methylphenyl)-3(2H)pyridazinone
(general name: diclomezine)
[0043] (20) (Z)-2'-Methylacetophenone=4,6-dimethyl
pyrimidin-2-ylhydrazone (general name: ferimzone)
[0044] (21) 1,1'-Iminiodi (octamethylene) diguanidium=triacetate
(general name: guazatine)
[0045] (22)
2-p-Chlorophenyl-2-(1H-1,2,4-triazol-1-ylmethyl)hexanenitrile
(general name: myclobutanil)
[0046] (23)
(RS)-2-(2,4-Dichlorophenyl)-1-(1H-1,2,4-triazol-1-yl)hexan-2-o- l
(general name: hexaconazole)
[0047] (24)
1-(4-Chlorophenoxy)-3,3-dimethyl-1-(1,2,4-triazol-1-yl)-2-buta-
none (general name: triadimefon)
[0048] (25)
N-Propyl-N-[2-(2,4,6-trichlorophenoxy)ethyl]-imidazole-1-carbo-
xamide (general name: prochloraz)
[0049] (26)
cis-4-[3-(4-tert-butylphenyl)-2-methylpropyl]-2,6-dimethylmorp-
holine (general name: fenpropimorph)
[0050] (27) Methyl=N-(2-methoxyacetyl)-N-(2,6-xylyl)-DL-alaninate
(general name: methalaxyl)
[0051] (28) Basic copper chloride (copper oxychloride)
[0052] (29) Basic copper sulfate (basic copper sulfate)
[0053] (30) Zinc ion-coordinated manganese
ethylenebis-dithiocarbamate (general name: mancozeb)
[0054] (31) Zinc propylenebisdithiocarbamate (general name:
propineb)
[0055] (32) Zinc dimethyldithiocarbamate (general name: ziram)
[0056] (33) Bis(dimethylthiocarbamoyl) disulfide (general name:
thiram)
[0057] (34) 1-(2-Cyano-2-methoxyiminoacetyl)-3-ethylurea (general
name: cymoxanil)
[0058] (35) Tetrachloroisophthalonitrile (general name:
chlorothalonil)
[0059] (36)
cis-trans-3-Chloro-4-[4-methyl-2-(1H-1,2,4-triazol-1-ylmethyl)-
-1,3-dioxolan-2-yl]phenyl=4-chlorophenyl=ether (general name:
difenoconazole)
[0060] (37) N-trichloromethylthiotetrahydrophthalimide (general
name: captan)
[0061] (38) Polyoxin (general name: polyoxin)
[0062] (39)
3-(3,5-Dichlorophenyl)-N-isopropyl-2,4-dioxoimidazolidine-1-ca-
rboxamide (general name: iprodione)
[0063] (40)
N-(3,5-Dichlorophenyl)-1,2-dimethylcyclopropane-1,2-dicarboxim- ide
(general name: procymidone)
[0064] (41) Methyl 1-(butylcarbamoyl)-2-benzimidazole-carbamate
(general name: benomyl)
[0065] (42) 1,2-Bis(3-methoxycarbonyl-2-thioureido)benzene (general
name: thiophanate-methyl)
[0066] (43) 2-(Methoxycarbonylamino)benzimidazole (general name:
carbendazin)
[0067] (44) Aluminum=tris(ethylphosphonate) (general name:
fosetyl)
[0068] (45) 3-Hydroxy-5-methylisoxazole (general name:
hymexazol)
[0069] (46)
5-Ethyl-5,8-dihydro-8-oxo[1,3]dioxolo[4,5-g]-quinoline-7-carbo-
xylic acid (general name: oxolinic acid)
[0070] (47)
4-(2,2-Difluoro-1,3-benzodioxol-4-yl)pyrrole-3-carbonitrile
(general name: fludioxonil)
[0071] (48) N-(4-Methyl-propa-1-ynylpyrimidin-2-yl)aniline (general
name: mepanipyrim)
[0072] (49) 4-Cyclopropyl-6-methyl-N-phenylpyrimidine-2-amine
(general name: cyprodinil)
[0073] (50) N-(4,6-Dimethylpyrimidin-2-yl)aniline (general name:
pyrimethanil)
[0074] (51) O-2,6-Dichloro-p-tolyl O,O-dimethyl-phosphorothioate
(general name: tolclofos-methyl)
[0075] (52) Mixture at arbitrary proportions of
N-(1-cyano-1,2-dimethylpro-
pyl)-2-(2,4-dichlorophenoxy)-propaneamide or optically active
compounds thereof or isomers thereof (the compounds disclosed in
JP-A-63-132867), and the like. These compounds can be used either
alone or in the form of a mixture of two or more compounds.
[0076] The plant disease controlling composition of the present
invention obtained by combining a 1,2,3-thiadiazole derivative
represented by the general formula (I) or a salt thereof with at
least one compound selected from the Compound Group I exhibits an
excellent controlling effect against the plant diseases exemplified
below. Further, the composition of the invention exercises an
effect also against the fungi resistant to the existing fungicidal
agents.
[0077] Roughly saying, the plant diseases on which the composition
exhibits an effect are classified in to mold fungi diseases,
bacterial diseases and viral diseases. For instance, there are
included the diseases due to Deuteromycetes such as Genus Botrytis,
Genus Helminthosporium, Genus Fusarium, Genus Septoria, Genus
Cercospora, Genus Pyricularia and Genus Alternaria, the diseases
due to Basidiomycetes such as Genus Hemileia, Genus Rhizoctonia and
Genus Puccinia, the diseases due to Ascomycetes such as Genus
Venturia, Genus Podosphaera, Genus Erysiphe, Genus Monilinia and
Genus Unsinula, the diseases due to the other fungi such as Genus
Ascochyta, Genus Phoma, Genus Pythium, Genus Corticium and Genus
Pyrenophora, the diseases due to bacteria such as Genus
Pseudomonas, Genus Xanthomonas and Genus Erwinia, and the diseases
due to viruses such as tobacco mosaic virus.
[0078] Specific examples of the diseases against which the
composition of the present invention exhibit a marked effect
include rice blast (Pyricularia oryzae), rice sheath blight
(Rhizoctonia solani), rice Helminthosporium leaf spot (Cochliobolus
miyabeanus), rice seedling blight (Rhizopus chinensis, Pythium
graminicola, Fusarium graminicola, Fusarium roseum, Mucor sp.,
Phoma sp., Tricoderma sp. ), rice bakanae disease (Gibberella
fujikuroi), powdery mildew of barley and wheat (Erysiphe graminis),
powdery mildew of cucumber (Sphaerotheca fuliginea), powdery mildew
of other host plants, eye spot of barley and wheat
(Pseudocercosporella herpotrichoides), flag smut of wheat, etc.
(Urocystis tritici), snow mold of barley and wheat (Fusarium
nivale, Pythium iwayamai, Typhla ishikariensis, Sclerotinia
boreasis), oats crown rust (Puccinia coronata), stem rust of other
plants, gray mold of cucumber and strawberry (Botrytis cinerea),
sclerotinia rot of tomato and cabbage (Sclerotinia sclerotiorum),
late blight of potato and tomato (Phytophthora infestans),
Phytophthora rot of other plants, downy mildew of various plants
such as cucumber downy mildew (Pseudoperonospora cubensis), grape
downy mildew (Plasmopara viticola), etc., apple scab (Venturia
inaequalis), apple Alternaria leaf spot (Alternaria mali), pear
black spot (Alternaria kikuchiana), citrus melanose (Diaporthe
citri), citrus scab (Elsinoe fawcetti), sugar beet Cercospora leaf
spot (Cercospora beticola), peanut brown leaf spot (Cercospora
arachidicola), peanut leaf spot (Cercospora personata), septoria
leaf spot of wheat (Septoria tritici), glume blotch of wheat
(Septoria nodorum), scald of barley (Rhynchosporium secalis), bunt
of wheat (Tilletia caries), lawn grass brown patch (Rhizoctonia
solani), lawn grass dollar spot of lawn grass (Sclerotinia
homoeocarpe); bacterial diseases due to Genus Pseudomonas such as
cucumber bacterial blight (Pseudomonas syringae py. lachrymans),
tomato bacterial wilt (Pseudomonas solanacearum) and rice glume
blight (Pseudomonas glumae), bacterial diseases due to Genus
Xanthomonas such as cabbage black rot (Xanthomonas campestris),
rice bacterial leaf blight (Xanthomonas oryzae) and citrus canker
(Xanthomonas citri), and bacterial diseases due to Genus Erwinia
such as cabbage bacterial soft rot (Erwinia carotovora), and viral
diseases such as tobacco mosaic (tobacco mosaic virus), etc.
[0079] The plants to which the fungicidal composition of the
present invention can be applied are not particularly limited, and
the following plants can be referred to as examples thereof:
[0080] cereals such as rice, barley, wheat, rye, oat, corn,
kaoliang, etc.; beans and peas such as soybean, red bean, broad
bean, pea, peanut, etc.; fruit trees and fruits such as apple,
citrus trees and fruits, pear, grape, peach, plum, cherry, walnut,
almond, banana, strawberry, etc.; vegetables such as cabbage,
tomato, spinach, broccoli, lettuce, onion, stone-leek, Spanish
paprika, etc., root crops such as carrot, potato, sweet potato,
radish, lotus rhizome, turnip, etc.; processing crops such as
cotton, flax, paper mulberry, mitsumata, rape seed plant, beet,
hop, sugar cane, sugar beet, olive, gum, coffee, tobacco, tea,
etc.; cucurbitaceous plants such as pumpkin, cucumber, 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.; and flower plants
such as chrysanthemum, rose, orchid, etc.
[0081] In order to control various diseases, the fungicidal
composition of the present invention is put to use either as it is
or in the form of a dilution or a suspension in a proper quantity
of water or the like by applying a quantity for effectively
exhibiting the plant disease controlling effect to the plant on
which an occurrence of the disease is expected or a site at which
occurence of the disease is to be prevented. For instance, with the
aim of controlling the disease of paddy field rice plant, it may be
applied to paddy field water or boxes for raising rice seedlings,
or by the method of seed coating, seed soaking or the like. Against
the diseases occurring in the upland field of fruit plants,
cereals, vegetables, etc., not only the treatment of leaves and
stalks but also immersion of seeds in the agent solution, treatment
of seeds with powdery agent or treatment of soil aiming at
absorption from the roots can also be adopted. It may also be used
for treatment of water culture solution for use in water
cultures.
[0082] As the method of treating seeds, a method of dipping seeds
in a diluted or undiluted liquid preparation 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.
[0083] 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 so-called seeds but also plant bodies for nutrient reproduction
such as bulb, tuber, seed tuber, aerial tuber, scaly bulb, stalks
for cuttage, and the like.
[0084] 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, seedling mat,
water and the like can also be used. Specific examples of the
material constituting the soil or cultivation carrier include sand,
vermiculite, cotton, paper, diatomaceous earth, agar, gelatinous
materials, polymeric materials, rock wool, glass wool, wood chips,
bark, pumice and the like.
[0085] As method for spraying the composition to the stalks and
leaves, a method of diluting a liquid preparation such as
emulsifiable concentrate, flowable agent or a solid preparation
such as wettable powder or wettable granular composition with a
proper quantity of water and then spraying the dilution to leaves
and stalks and a method of spraying the powdery composition can be
referred to.
[0086] As method for applying the composition to the soil, a method
of applying a liquid preparation either diluted or undiluted with
water to the base of stalks, seedling bed for raising seedlings or
the like, a method of spraying a granular agent to the stalk base
or seedling 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.
[0087] For applying the fungicide of the present invention to a
seedling box of paddyfield riceplant, the fungicide may be applied
in the form of a dust, a wettable granular composition or a
granular composition, though the preparation form may be dependent
on the time of application or whether it is applied at the seeding
time, in the greening period or at the time of transplantation.
Otherwise, the fungicide may also be applied by mixing it into a
molding. A molding may be mixed with a dust, a wettable granule or
a granular composition by the method of bed soil mixing, covering
soil mixing or mixing into the whole mold. It is also possible to
form alternating layers of molding and fungicidal composition. When
the fungicide is applied at the seeding time, the time of
application of the fungicide may be any of before the seeding,
simultaneous with the seeding and after the seeding, or it also be
after coverage of soil.
[0088] For applying the fungicide to 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 its mixture with
fertilizers into soil at the time of transplantation of rice
seedlings. It is further possible to apply an emulsifiable
concentrate, a wettable powder or a flowable preparation to the
water inlet or water flow source of irrigating apparatus, by which
the fungicide can be applied together with water supplied to the
paddy field in a labor-saving manner.
[0089] In case of upland field crops such as wheat, a fungicidal
composition 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 fungicide may directly be applied to the seeds to
make seed coating, or may also be applied to the base of hills to
achieve a successful result. It is also possible to scatter a
granular preparation, or to apply a liquid preparation after being
diluted with water or without dilution.
[0090] In cases where cultured plants to be transplanted are
treated at the seeding time or in the seedling raising period,
preferable are a direct treatment of seeds, an irrigating treatment
using a liquefied agent or a powdering treatment of granular agent
to the seedling-raising bed. Further, application of granular agent
to the planting holes at the time of set-planting and mixing of a
fungicide into the cultivation carrier in the neighborhood of the
sites of transplantation are also preferable.
[0091] As for the dosage of the active ingredient compound of the
plant disease controlling composition of the present invention, at
least one compound properly selected from the Compound Group I is
used usually in an amount of 0.01-1,000 parts by weight and
preferably 0.1 to 100 parts by weight, per part by weight of the
1,2,3-thiadiazole derivative of general formula (I) or a salt
thereof.
[0092] The plant disease controlling composition of the present
invention may be applied in a preparation form of, for instance,
emulsifiable concentrate, wettable powder, suspension, solution,
granule, dust or the like. Although the dosage thereof varies
depending on the content of active ingredient in the composition,
climate conditions, preparation form, time of application, method
of application, place of application, disease to be controlled and
objective crop plant, the dosage is appropriately selected usually
from a range of 0.1-1,000 grams and preferably 1-50 grams as
expressed in terms of weight of active ingredient, per are of the
field. In the case of seed treatment, the weight of active
ingredient may be changed in the range of 0.01-40% based on the
seed. When emulsifiable concentrate, wettable powder, suspension or
solution is diluted with water and then put to use, the
concentration at the time of application is 0.0001-0.1%. In the
cases of a granular composition, a dust composition and a liquid
composition to be used for seed treatment, the compositions may
directly be put to use without dilution.
EXAMPLE
[0093] Next, typical examples and test examples of the present
invention are presented below. The invention is by no means limited
by these examples. In the examples, the term "part" means part by
weight.
4 The compound of Table 1 or 3 10 parts One compound of Compound
Group I 10 parts Calcined diatomaceous earth 63 parts
Polyoxyethylene nonylphenyl ether 5 parts Naphthalenesulfonic acid-
4 parts formaldehyde condensate Silicic acid hydrate 8 parts
[0094] A wettabel powder is prepared by uniformly mixing and
grinding the ingredients mentioned above. Example 2
5 Compound of Table 1 or 3 10 parts One compound of Compound Group
I 35 parts Calcined diatomaceous earth 28 parts Polyoxyethylene
nonylphenyl ether 5 parts Naphthalenesulfonic acid- 4 parts
formaldehyde condensate Silicic acid hydrate 8 parts
[0095] A wettable powder is prepared by uniformly mixing and
grinding the ingredients mentioned above. Example 3
6 Compound of Table 1 or 3 40 parts One compound of Compound Group
I 10 parts Calcined diatomaceous earth 33 parts Polyoxyethylene
nonylphenyl ether 5 parts Naphthalenesulfonic acid- 4 parts
formaldehyde condensate Silicic acid hydrate 8 parts
[0096] A wettable powder is prepared by uniformly mixing and
grinding the ingredients mentioned above. Example 4
7 Compound of Table 1 or 2 5 parts One compound of Compound Group I
7 parts Synthetic silicic acid hydrate 1 part Calcium
ligninsulfonate 2 parts Bentonite 30 parts Kaolin clay 55 parts
[0097] A granular composition is prepared by uniformly mixing and
grinding the ingredients mentioned above, adding an appropriate
quantity of water, and kneading and drying the resulting
mixture.
Example 5
[0098]
8 Compound of Table 1 or 3 20 parts One compound of Compound Group
I 20 parts Sodium alkylnaphthalenesulfonate 3 parts Propylene
glycol 5 parts Dimethylpolysiloxane 0.25 part p-Chloro-m-xylenol
0.10 part Xanthane gum 0.30 part Water 51.35 parts
[0099] A wettable powder or an aqueous suspension is prepared by
uniformly mixing and grinding the ingredients mentioned above.
Test Example 1
Preventive Effect on Rice Blast by Spraying
[0100] A wettable powder prepared according to the examples
mentioned above and diluted with water to a predetermined
concentration was sprayed to stalks and leaves of rice plants
(variety: Kimmaze) of 6-leaved stage cultivated in pots. After the
spraying, the pots were cultivated in a greenhouse. Seven days
after the treatment, the plants were inoculated with a spore
suspension of rice blast fungi (Pyricularia oryzae) by the method
of spraying.
[0101] After the inoculation, the plants were left to stand for 7
days at 20.degree. C. under a high humidity condition, and then the
number of lesions was counted, from which controlling degree was
calculated according to the equation mentioned below. In
the-untreated-plot, the number of lesions was 23.0 per leaf. 1
Controllingdegree (%) = Number of lesions in untreated plot -
Number of lesions in treated plot Number of lesions in untreated
plot .times. 100
[0102] Further, the theoretically expected controlling degree was
calculated according to the following formula:
Theoretically expected controlling degree (%)=X+(100-X)-Y/100
[0103] wherein X is controlling degree (%) of agent A at 12.5 ppm
and Y is controlling degree (%) of agent B at 12.5 ppm (the portion
which could not be controlled with agent A corresponded to
(100-X)%, of which Y%, namely (100-X).times.Y/100, was controlled
by agent B.
[0104] The results are shown in Table 4.
9TABLE 4 Concen- Actual Theoretical tration controlling controlling
Test agent (ppm) degree (%) degree (%) Compound No. 3 + 12.5 + 12.5
64 42 Isoprothiolane Compound No. 3 + 12.5 + 12.5 70 43
Tricyclazole Compound No. 3 12.5 27 Isoprothiolane 12.5 20
Tricyclazole 12.5 22
Test Example 2
Preventive Effect on Barley Powdery Mildew by Spraying
[0105] A wettable powder prepared according to the examples
mentioned above and diluted to a predetermined concentration was
applied to stalks and leaves of barley plant (variety: Kanto No. 6)
of 2-leaved stage cultivated in pots. After the spraying, the pots
were cultivated in a greenhouse. Seven days after the treatment,
the plants were inoculated with spores of powdery mildew (Erysiphe
graminis) by the method of powdering. Seven days after the
inoculation, the number of lesions was counted, from which
controlling degree was calculated according to Test Example 1. In
the untreated plot, the number of lesions was 17.7 per leaf. The
theoretical controlling degree was calculated in the same manner as
in Test Example 1.
[0106] The results are shown in Table 5.
10TABLE 5 Concen- Actual Theoretical tration controlling
controlling Test agent (ppm) degree (%) degree (%) Compound No. 3 +
20 + 20 87 66 Azoxystrobin Compound No. 3 + 20 + 20 85 67
Propiconazole Compound No. 3 20 15 Azoxystrobin 20 60 Propiconazole
20 63
Test Example 3
Preventive Effect on Cucumber Downy Mildew by Spraying
[0107] A wettable powder prepared according to the examples
mentioned above was diluted with water to a predetermined
concentration and sprayed to stalks and leaves of cucumber
(variety: Suyo) of 2.5-leaved stage cultivated in pots. After the
spraying, the pots were cultivated in a greenhouse. Six days after
the treatment, the plants were inoculated with zoospores of downy
mildew (Pseudoperonospora cubensis). Seven days after the
inoculation, the plants were examined and the disease occurrence
index was determined according to the criterion shown below, from
which controlling degree was calculated according to the following
equation. In the untreated plot, the disease occurrence index was
7.8. The theoretical controlling degree was calculated in the same
manner as in Test Example 1.
[0108] Disease Occurrence Index
[0109] 0: No occurrence of disease
[0110] 1: Areal rate of lesion: 1-10%
[0111] 2: Areal rate of lesion: 11-20%
[0112] 3. Areal rate of lesion: 21-30%
[0113] 4. Areal rate of lesion: 31-40%
[0114] 5: Areal rate of lesion: 41-50%
[0115] 6: Areal rate of lesion: 51-60%
[0116] 7: Areal rate of lesion: 61-70%
[0117] 8: Areal rate of lesion: 71-80%
[0118] 9: Areal rate of lesion: 81-90%
[0119] 10: Areal rate of lesion: 91-100% 2 Controlling degree ( % )
= Disease occurrence index in untreated plot - Disease occurrence
index in treated plot Disease occurrence index in untreated plot
.times. 100
[0120] The results are shown in Table 6.
11TABLE 6 Theoretical Concen- Controlling controlling tration
degree degree Test agent (ppm) (%) (%) Compound NO. 3 + 50 + 50 75
60 8-Hydroxyquinoline- copper Compound No. 3 50 20
8-Hydroxyquinoline- 50 50 copper
Test Example 4
Control Test on Cabbage Black Rot
[0121] A wettable powder composition prepared according to the
examples mentioned above was diluted with water to a predetermined
concentration and sprayed to cabbage (variety: Kinkei No. 201) of
early head forming period four times at intervals of 7 days of 280
liters per 10 ares. Two days after the second spraying, the cabbage
was inoculated with an aqueous suspension of cabbage black rot
bacterium (Xanthomonas campestris) by the method of spraying. Two
weeks after the final spraying, the cabbage was investigated to
calculated the degree of disease occurrence according to the
following criterion. In the untreated plot, the degree of disease
occurrence was 44.7. Theoretical controlling degree was calculated
in the same manner as in Test Example 1
Degree of disease occurrence=.SIGMA.(Number of hills at every
degree of occurrence).times.100.div.(Number of hills
investigated.times.3)
12 Index State of disease occurrence 0: No occurrence of disease or
only very slight number of lesions 1: Lesions are sporadically
found on a few outer leaves. 2: Rather many lesions are found on
all the outer leaves. 3: Many lesions are found on all the outer
leaves, and some of the heads are diseased.
[0122] From the degree of disease occurrence, controlling degree
was calculated according to the following equation. Theoretical
controlling degree was calculated in the same manner as in Test
Example 1. 3 Controlling degree (%) = Degree of disease occurence
in untreated plot - degree of disease occurence in treated plot
Degree of disease occurence in untreated plot .times. 100
[0123] The results are shown in Table 7.
13TABLE 7 Control- Concen- Percentage Degree of ling Theoretical
tration of diseased disease degreee controlling Test agent (ppm)
hills (%) occurrence (%) degree (%) Compound No. 3 + 100 + 350 27.0
9.0 80 59 8-Hydroxyquinoline- copper compound No. 3 100 98.2 52.8 0
8-Hydroxyquinoline- 350 54.5 18.2 59 copper
Test Example 5
Controlling Test on Cucumber Bacterial Blight
[0124] A wettable powder composition prepared according to the
examples mentioned above was diluted with water to a predetermined
concentration and sprayed to cucumber (variety: Topgreen) of growth
period three times, at intervals of 7 days of 280 liters per 10
ares. Six hours after the first spraying, the cucumber was
inoculated with an aqueous suspension of cucumber bacterial blight
bacterium (Pseudomonas syringae pv. lachrymans) by the method of
spraying. One week after the final spraying, the cucumber was
investigated to calculated the degree of disease occurrence
according to the following criterion. In the untreated plot, the
degree of disease occurrence was 63.9. Theoretical controlling
degree was calculated in the same manner as in Test Example 1.
Degree of disease occurrence=.SIGMA.(Number of diseased leaves at
every degree of disease
occurrence.times.index).times.100.div.(Number of hills
investigated.times.4)
14 Index State of disease occurrence 0: No disease occurrence 1:
Areal rate of disease occurrence: less than 5% 2: Areal rate of
disease occurrence: no less than 5% and less than 25% 3: Areal rate
of disease occurrence: no less than 25% and less than 50%
[0125] 4: Areal rate of disease occurrence: no less than 50%.
[0126] From the degree of disease occurrence, controlling degree
was calculated according to Test Example 4. The theoretical
controlling degree was calculated in the same manner as in Test
Example 1.
[0127] The results are shown in Table 8.
15TABLE 8 Percentage Theoretical Concentration of diseased
Controlling controlling Test agent (ppm) leaves (%) degree (%)
degree (%) Compound 3 + 100 + 350 33.3 67 47 8-Hydroxyquinoline-
copper Compound 3 100 53.9 46 8-Hydroxyquinoline- 350 99.4 1
copper
Test Example 6
Controlling Test on Wheat Powdery Mildew
[0128] A wettable powder prepared according to the examples
mentioned above was applied to wheat in the internode elongation
period of 100 liters per 10 ares. Two months after the chemical
treatment, areal rate of lesion on the flag leaves was measured,
from which controlling degree was calculated according to the
following equation. In the untreated plot, the areal rate of lesion
was 15%. The theoretical controlling degree was calculated in the
same manner as in Test Example 1. 4 Controlling degree ( % ) =
Areal rate lesion in untreated plot - Areal rate of lesion in
treated plot Area rate of lesion in untreated plot .times. 100
[0129] The results are shown in Table 9.
16TABLE 9 Theoretical Dosage Controlling controlling Test agent
(ppm) degree (%) degree (%) Compound No. 3 + 200 + 100 83 56
Azoxystrobin Compound No. 55 + 200 + 100 70 44 Azoxystrobin
Compound No. 3 200 27 Compound No. 55 200 7 Azoxystrobin 100 40
Test Example 7
Controlling Test on Tobacco Mosaic Virus Disease
[0130] A wettable powder prepared according to the examples
mentioned above was diluted with water to a predetermined
concentration, and sprayed to a tobacco plant of 5-leaved stage
(variety: Samson NN). Seven days after the chemical treatment, the
tobacco leaves, previously powdered with 60 mesh Carborundum, was
inoculated by lightly patting the leaf surface with cotton
applicator immersed in a 10 .mu.g/ml solution of tobacco mosaic
virus in phosphate buffer (pH 6.8). Just after the inoculation, the
Carborundum was washed away with running water, and the plant was
left to stand in a greenhouse until local lesions were formed.
Then, diameters of lesions were measured, from which controlling
degree was calculated according to the following equation. In the
untreated plot, diameter of the lesion was 2.2 mm. The theoretical
controlling degree was calculated in the same manner as in Test
Example 1. 5 Controlling degree ( % ) = Diameter of lesion in
untreated plot - Diameter o f lrdin in treated plot Diameter of
lesion in untreated plot .times. 100
[0131] The results are shown in Table 10.
17TABLE 10 Theoretical Dosage Controlling controlling Test agent
(ppm) degree (%) degree (%) Compound No. 3 + 200 + 200 35 20
Isoprothiolane Compound No. 3 200 20 Isoprothiolane 200 0
Test Example 8
Controlling Effect on Rice Bakanae Disease by Seed Coating
Treatment
[0132] Unhulled rice seeds (variety: Kimmaze) infected with rice
bakanae disease fungi (Gibberella fujikuroi) were subjected to a
powder coating treatment by introducing the rice seeds into a vinyl
bag together with a wettable powder prepared according to the
examples mentioned above and thoroughly mixing them together with a
small quantity of water. After the treatment, the unhulled rice was
air-dried overnight, immersed in water at 15.degree. C. for one
week, and then kept at 30.degree. C. to promote germination, after
which the unhulled rice seeds were sown in a seedling raising box,
germination thereof was hastened at 30C for 3 days, and the plants
were cultivated in a greenhouse for about one month. Then, the
diseased seedling rate was investigated, from which the controlling
degree was calculated according to the following equation. In the
untreated plot, the diseased seedling rate was 78%. The theoretical
controlling degree was calculated in the same manner as in Test
Example 1. The results are shown in Table 11, 6 Controlling degree
( % ) = Diseased seedling rate in untreated plot - Disease seedling
rate in treated plot Diseased seedling rate in untreated plot
.times. 100
[0133] The results are shown in Table 11.
18TABLE 11 Dosage (wt. % of active ingredient per dry Controlling
Theoretical unhulled degree controlling Test agent rice) (%) (%)
degree (%) Compound No. 55 + 0.2 + 0.2 75 45 Oxolinic acid Compound
No. 55 0.2 45 Oxolinic acid 0.2 0
Test Example 9
Controlling Effect on Cucumber Downy Mildew by Soil Mixing
Treatment
[0134] A wettable powder prepared according to the examples
mentioned above was mixed into soil, and the soil thus obtained was
filled into pots so that one pot contained 5 g of the wettable
powder. Then, cucumber (variety: Suyo) seedlings of
cotyledon-developing period were transplanted into the pots. After
cultivating the pots in a greenhouse for 2 weeks, the plants were
inoculated with zoospores of downy mildew (Pseudoperonospora
cubensis). Seven days after the inoculation, the plants were
investigated and evaluated according to Test Example 3, from which
controlling degree was determined. In the untreated plot, the
disease occurrence index was 6.5. The theoretical controlling
degree was calculated in the same manner as in Test Example 1.
[0135] The results are shown in Table 12.
19TABLE 12 Dosage (amt. of active Theoretical ingredient
Controlling controlling Test agent per pot) (g) degree (%) degree
(%) Compound No. 55 + 0.1 + 0.1 72 41 Benomyl Compound No. 55 0.1
40 Benomyl 0.1 2
Test Example 10
Controlling Effect on Wheat Powdery Mildew by Seed Coating
Treatment
[0136] Seeds of wheat (variety: Chihoku) and a wettable powder
prepared according to the examples mentioned above were introduced
into a vinyl bag. A small quantity of water was added thereto and
thoroughly mixed together to carry out a seed coating treatment.
After the treatment, the seeds were air-dried overnight, sown in
pots, and cultivated in a greenhouse. One month after the seeding,
the plants were inoculated with spores of powdery mildew (Erysiphe
graminis) by the method of powdering. Seven days after the
inoculation, the number of lesions was counted, from which
controlling degree was calculated according to Test Example 1. In
the untreated plot, the number of lesions per leaf was 25. The
theoretical controlling degree was calculated in the same manner as
in Test Example 1.
[0137] When only the compound formula (I) is used, the result of
seed treatment is superior to the result of spraying to stalks and
leaves in course of cultivation (for instance, Test Example 2 and
Test Example 6) in terms of dosage per area of cultivation.
Further, when the mixed agent according to the present invention is
used for the seed treatment, the activity is more enhanced, and the
effect exhibited is far more excellent than that achieved by
spraying a single agent.
20TABLE 13 Dosage (amt. of active ingredient Controlling
Theoretical per dry seed degree controlling Test agent weight) (%)
(%) degree (%) Compound No. 55 + 1 + 1 96 88 Benomyl Compound No.
55 1 88 Benomyl 1 0
* * * * *