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(11)    Patent Number: KE 605   

( 45)    Date of grant: 0 1/07/2013   
       
(51) Int.Cl.8: A 01N 37/18, 37/50, 43/54, 47/16, 47/24, A 01P 3/00

(21)Application Number: KElP/ 2012/001631

(22) Filing Date: 24/03/2009

(30) Priority data: 2008-086238  28/03/2008  JP

(86)  PCT data PCT/JP2009/056426 24/03/2009 wo 2009/119872 01/10/2009

(73) Owner: SUMITOMO CHEMICAL COMPANY LIMITED of 27-1, Shinkawa 2-chome, Chuo-ku, Tokyo 104- 8260,Japan

(72) Inventors: SOMA, Masato, 2-10-3-328, Sonehigashino-cho, Toyonaka-shi, Osaka 5610802, Japan and TAKAISHI, Masanao, 2-11-7-203, Sonehigashino-

cho, Toyonaka-shi, Osaka 5610802, 5610802, Japan

(7 4) Agent/address for correspondence: Waruinge & Waruinge Advocates, P.O.BOX 72384-00200, Nairobi
 
(54)    Title:PLANT DISEASE CONTROLLING COMPOSITION AND METHOD FOR CONTROLLING PLANT DISEASE

(57)    Abstract: A plant disease controlling composition comprising, as active ingredients, a compound represented by the formula (I), as well as at least one compound A selected from the group consisting of dimoxystrobin, trif loxystrobin, azoxystrobin, pyraclostrobin, a compound represented by the formula (II) and an agrochemically acceptable salt of the compound represented by the formula (II) : wherein, Rl, Q, X, Y, Z, M and n are as defined in the description.

DESCRIPTIONPLANT  DISEASE  CONTROLLING  COMPOSITION  AND

METHOD  FOR  CONTROLLING  PLANT  DISEASE

5

Technical  Field

The present invention relates to a plant disease controlling composition and a method of controlling a plant disease.

10

Background  Art

Heretofore, while various plant disease controlling agents have been developed (see e.g. WO 95/27693 A1, EP 477631 A, JP 2000-226374 A), a plant disease controlling

15    agent  having  higher  activity  is  always  demanded.



Disclosure  of  the  Invention

An object of the present invention is to provide a plant dise~se controlling composition showing high plant

20    disease controlling activity, and a method for effectively controlling a plant disease.



Under these circumstances, the present inventors have intensively studied and, as a result, have found thatan

excellent  plant  disease  controlling  effect  can  be  obtained

25    by  applying  a  compound  represented  by  the  following  formula

(I) and a specific compound. Thus, the present invention has been completed.


That  is,   the•present  invention  provides:

(i) A plant disease controlling composition comprising, 5 as active ingredients, a compound represented by the

formula    (I) :

H3C

dH-CH3

referred to as the compound I in some cases), least one compound A selected from the group
 

10    consisting of dimoxystrobin, trifloxystrobin, azoxystrobin, pyraclostrobin, a compound represented by the formula (II) and an agrochemically acceptable salt of the_compound represented by the formula (II):

15    wherein, R1 represents a halogen atom, an optionally substituted alkyl group, an alkoxy group, a haloalkoxy group, an alkyl thio group, an alkylsulfinyl group., an alkylsulfonyl group, an optionally substituted amino group or a nitro group, Q represents an optionally substituted

aryl group, an optionally substituted heterocyclic group, a mono- or di-substituted methyleneamino group, an optionally substituted alkyl group, an optionally substituted alkenyl

group,    an  optionally  substituted  alkyny~ group,   a

5    substituted  carbonyl  group  or  a  substituted  sulfonyl  grou~,

X represents a hydrogen atom, a halogen atom, an optionally substituted alkyl group, or an optionally substituted hydroxy group, Y represents an optionally substituted hydroxy group, an alkylthio group, or an optionally


10    substituted amino group, Z represents an oxygen atom or a sulfur atom, M represents an oxygen atom, S(O)r (wherein I represents an integer of 0, 1 or 2), NR2 (wherein, R2


represents a hydrogen atom, an alkyl group or an acyl group) or a single bond, and n represents an integer of 0,

15    1 or 2 (hereinafter, referred to as the compound ~I in some cases) (hereinafter, referred to as the present composition in some cases); and

(ii)    A method for controlling a plant disease, which comprises applying the compound I as well as at least one

20    compound A selected from the group consisting of dimoxystrobin, trifloxystrobin, azoxystrobin, pyraclostrobin, the compound II and the agrochemically
 

acceptable salt of the compound represented by the formula (II) to a plant, a seed of a plant or a cropland

25    (hereinafter,   referred  to  as  the  present  controlling  method

in  some  cases)  .

According to the present invention, a plant disease controlling composition showing high plant disease controlling activity, and a method for effectively

5    controlling  a  plant  disease  can  be  provided.



Best  Mode  for  Carrying  Out  the  Invention

The    compound  I   is  described,   for  example,   in  JP  2000-

.226374  A.    The  compound  can  be  synthesized,   for  example,  by

10    the method described in the aforementioned publication, or a known method.



Dimoxystrobin, trifloxystrobin, azoxystrobin, pyraclostrobin, the compound II and the salts of the compound II show inhibitory activity on an electron

15    transport system complex III.• These compounds show an effect of controlling a plant disease synergistically with the compound I .

Dimoxystrobin  is  a  general  name  of   (aE)-2-[(2,5-

dimethylphenoxy)methyl]-a-(methoxyimino)-N-

20 methylbenzeneacetamino, which is described in EP 477631 A. Trifloxystrobin is a general name of methyl (E)-

methoxyimino-{ (E)-a-[1-(a,a,a-trifluoro-m-tolyl]ethylideneaminooxy)-o-tolyl}acetate, which is described, for example, in pages 1074 to 1075 of The

25    Pesticide  manual  Fourteenth.

Azoxystrobin  is  a  general  name  of  methyl   (E)-2-{2-[6-

(2-cyanophenoxy)pyrimidin-4~yloxy]phenyl}-3-methoxyacrylate,

which  is  described,   for  example,   in  pages  54  to  56  of  Th~

Pesticide  manual  Fourteenth.

5 Pyraclostrobin is a general name of methyl 2-[[1-(4-chlorophenyl)-1H-pyrazol-3-yloxymethyl]phenyl] (N-methoxy)carbamate, which is described, for example, in pages 900 to 901 of The Pesticide manual Fourteenth.

The  compound  II  and  an  agrochemically  acceptable  salt

10    thereof  are  descr~bed in  WO  95/27693  A1.

These respective compounds can be prepared .by the methods described in the aforementioned publications, or a known method.

As  used  herein,   the  agrochemically  acceptable  salt

15    means a salt which can be applied as an agrochemical or a starting material for an agrochemical.

The  compound  II  .is  represented  by  the  formula   (II)  .

Examples of the '.'halogen atom" represented by R1 include fluorine, chlorine, bromine and iodine.

20 Examples of the "alkyl group" represented by R1 include an alkyl group having 1 to 8 carbon atoms. Examples of the alkyl group include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a tert-butyl group, a pentyl


25    group.,   and  a  hexyl  group.

Among them, an alkyl group having 1 to 4 carbon atoms is preferable, and a methyl group and an ethyl group are particularly preferable.

Examples  of  the  substituent  of  the  "optionally

5    substituted alkyl group" include a halogen atom (e.g. fluorine, chlorine, bromine, iodine, preferably fluorine); an alkoxy group having 1 to 8, preferably 1 to 4 carbon atoms (e.g. methoxy group, ethoxy group, propoxy group, or


butoxy  group) .

10 Examples o.f the "substituted alkyl group" include a haloalkyl group (e.g. difluoromethyl group, trifluoromethyl group, chloromethyl group, 2-bromoethyl group, or •2,3-dichloropropyl group); and an alkoxyalkyl group (e.g. methoxymethyl group, ethoxyrnethyl group, or methoxyethyl


15    group) . As the haloalkyl group, a fluoroalkyl group having 1 to 4 carbon•atoms is preferable, and a trifluoromethyl group is more preferable. As the alkoxyalkyl group, an alkoxyalkyl group having 1 to 3 carbon atoms in total is preferable, and a methoxymethyl group is more preferable.


20 Examples of the "alkoxy group" represented by R1 include an alkoxy group having 1 to 8 carbon atoms, preferably, an alkoxy group having 1 to 4 carbon atoms such as a methoxy group, an ethoxy group, or a propoxy group.


Examples  of  the  "haloalkoxy  group"  represented  by  R1

25    include  a  haloalkoxy  group  having  1  to  8  carbon  atoms,
 
preferably a haloalkoxy group havi.ng 1 to 4 carbon atoms, more preferably a fluoroalkoxy group having 1 to 4 carbon atoms.

Examples  of  the  "alkylthio  group"  represented  by  R1

5    include an alkylthio group having 1 to 8, preferably 1 to 4 carbon atoms, specifically, a methylthio group, an ethylthio group, a propylthio group, and a butylthio group.

Among them, a methylthio group is preferable. Examples of the "alkylsulfinyl group" represented by

10.    R1   include  an  alkylsulfinyl  group  having  1  to  8,  preferably
    1  to  4  carbon  atoms,   specifically,   a  methylsulfinyl  group,
    an  ethylsulfinyl  group,   and  a  propylsulfinyl  group.
    Among  them,   a  methylsulfinyl  group  is  preferable.
    Examples  of  the  "alkylsulfonyl  group"  represented  by
15    R1   include  an  alkylsulfonyl  group  having  1  to  8,  preferably
    1  to  4  carbon  atoms,   specifically,   a  methylsulfonyl  group,
    an  ethylsulfonyl  group,   and  a  propylsulfonyl  group.
    Among  them,   a  methylsulfonyl  group  is  preferable.
    Examples  of  the  "optionally  substituted  amino  group"
20    represented  by  R1  include  an  amino  group,   an  amino  group
    mono-  or  di-substituted  with  an  alkyl  group  having  1  to  8,
    preferably  1  to  4  carbon  atoms   (e.g.  monomethylamino,
    dimethylamino,   or  monoethylamino),   an  amino  group  mono-
    substituted  with  a  formyl  group,   and  an  amino  grou.f:J  mu.uu-
25    substituted  with  an  alkylcarbonyl  group  having  2  to  8,
 
preferably 2 to 4 carbon atoms (e.g. methylcarbonylamino group). Among them, an amino group substituted with an alkyl group having 1 to 4 carbon atoms is preferable, and a

monomethylamino  group  is  particularly  preferable.

5 Preferable examples of R1 include a• halogen atom, an• alkyl group, a haloalkyl group, an alkoxyalkyl group, a hydroxy group, an alkoxy group, an alkenyloxy group, an alkynyloxy group, a haloalkoxy group, a haloalkenyloxy group, a haloalkynyloxy group, an alkoxyalkoxy group, an


10    alkylcarbonyloxy group, an (alkylthio)carbonyloxy group, an alkylsulfonyloxy group, an arylsulfonyloxy group, mono- or di-alkyl-substituted carbamoyloxy group, an aryloxy group,

an  alkylthio  group,   an  alkylsulfinyl  group,   an

alkylsulfonyl  group,   an  amino  group  optionally  substituted

15    with an alkyl group, a nitro group, and a tetrahydropyranyloxy group. More preferable examples

include a halogen atom, a C1-C4 alkoxy group, a Cl-C4 haloalkoxy group and a hydroxy group. Among them, a Cl-C4 alkoxy group, and a Cl-C4 haloalkoxy group are further

20    preferable, a rnethoxy group, an ethoxy group, and a difluoromethyl group are particularly preferable, and a methoxy group is most preferable.
 

Examples of the "optionally substituted ~ryl group" represented by Q• inc_lude an aryl group having 6 to 14

25    carbon  atoms  such  as  a  phenyl  group,   and  a  naphthyl  group.
 
When the aryl group is substituted, examples of the substituent include a lower alkyl group (e.g. methyl group ethyl group, propyl group, or butyl group), a lower alkenyl group (e.g. vinyl group, allyl group, or crotyl group), a


5    lower alkynyl group (e.g. ethynyl group, propargyl group, or butynyl group), a cycloalkyl group (e.g. cyclopropyl group. cyclopentyl group, or cyclohexyl group), an lower alkoxy lower alkyl group (e.g. methoxymethyl group,


ethyoxymethyl  group,  or  2-~ethoxyethyl group),   cycloalkenyl

10    group (e.g. cyclopen•tenyl group, or cyclohexenyl group)., a lower alkanoyl g.roup (e.g. acetyl group, propionyl group, or isobutyryl group), a lower alkylsilyl group (e.g.

trimethylsilyl group, triethylsilyl group, tripropylsilyl group, or tributylsilyl group), a halo(lower)alkyl group

15 (e.g. difluoromethyl group, trifluoromethyl group, chloromethyl group, 2-bromoethyl group, or 2,3-

dichloropropyl group), a di(lower)alkylamino group (e.g. dimethylamino group, or diethylamine group), a phenyl group, a phenyl(lower)alkyl group (e.g. benzyl group, or phenethyl

20    group), a phenyl(lower)alkenyl group (e.g. styryl group, or cinnamyl group), a furyl(lower)alkyl group (e.g. 3-furylmethyl group, or 2-furylethyl group), a
 

furyl(lower)alkenyl group (e.g. 3-furylvinyl group, or 2-furylallyl group), a halogen atom (e.g. fluorine, chlorine,

25    bromine,   iodine),   a  nitro  group,   a  cyano  group,   a  lower
 

alkylthio group (e.g. methylthio group, ethylthio group, or propylthio group), a lower alkoxycarbonyl group (e.g. rnethoxycarbonyl group, ethoxycarbonyl group, or propoxycarbonyl group) , a formyl group, •an amino group, a


5    mono{lower)alkylamino group (e.g. methylamine group, or ethylamino group), -OR [wherein R is a hydrogen atom, a lower alkyl group (e.g. methyl group, ethyl group, propyl group, or butyl group), a lower alkenyl group (e.g. vinyl


group, allyl group, or crotyl group), a lower alkynyl group 10 (e.g. ethynyl group, 2-propynyl group, or 3-butynyl group),

a halo(lower)alkyl group (e.g. difluoromethyl group, trifluoromethyl group, chloromethyl group, 2-bromoethyl group, or 2,3-dichloropropyl group), a lower alkanoyl group (e.g. acetyl group, propionyl group, or butyryl group), a


15    phenyl group, a lower alkoxyphenyl group (e.g. 3-methoxyphenyl group, or 4-ethoxyphenyl group), a nitrophenyl group (e.g. 3-nitrophenyl group, or 4-

nitrophenyl group), a phenyl(lower)alkyl group (e.g. benzyl group, phenethyl group, phenylpropyl group), a

20    cyanophenyl(lower)alkyl group (e.g. 3-cyanophenylmethyl group, or 4-cyanophenylethyl gro~p), a benzoyl group, a tetrahydropyranyl group, a pyridyl group, a

trifluoromethylpyridiyl  group,   a  pyrimidinyl  group,  a

•benzothiazolyl  group,   a  quinolyl  group,   a

25    benzoyl(lower)alkyl  group   (e.g.  benzoylmethyl  group,   or

benzoylethyl group), a benzenesulfonyl group, or a lower alkylbenzenesulfonyl group (e.g. toluenesulfonyl group)], and -CH2 -G-R' [wherein G is -0-, -8-, or -NR"- (wherein R"
is    a  hydrogen  atom  or  a  lower  alkyl  group),   and  R'   is  a

5    phenyl group, a halophenyl group (e.g. 2-chlorophenyl group, or 4-fluorophenyl group), a lower alkoxyphenyl group (e.g.

2-methoxyphenyl gro.up, or 4-ethoxyphenyl group), a pyridyl group, or a pyrimidinyl group].

These  substituents  may  be  at  any  possible  positions  of

10    the ring. The number of the substituents is 1 to 5, preferably 1 to 4, further pr~ferably 1 to 3. When there

are plural substituents, these may be the same or different. As used herein, the term "lower" means 1 to 8,

. preferably  1  to  6,  more  preferably  1  to  4  carbon  atoms.

15    The  "optionally  substituted  aryl  group"  represented  by

Q is preferably an optionally substituted phenyl group, more preferably a phenyl group optionally substituted with a halogen atom, a methyl group, a trifluoromethyl group or a methoxy group, further preferably a 2,5-dimethylphenyl


•20    group.

Examples  of  the  "optionally  substituted  heterocyclic

group" represented by Q include a 5- to 7- membered heterocyclic group containing 1 to 4 hetero atoms selected from nitrogen, oxygen and sulfur as ring constituting

25    atom(s).    These  heterocyclic  groups  may  form  a  fused  ring


wherein  R12   and  R13   represent  independently  a  hydrogen  atom,

an  optionally  substituted  alkyl  group,   an  acyl  group,   an

5    •alkylthio group, an alkylsulfinyl group, an alkylsulfonyl group, an optionally substituted arnipo group, a cycloalkyl group, an optionally substituted aryl group, or an optionally substituted heterocyclic group., or R12 and R13


together  form  a  roonocycle  or  a  polycycle  optionally

10    containing hetero atom(s) (provided that, the case where R12 and R13 are a hydrogen atom at the same time is
excluded)].

In  the  formula   (a),  examples  of  the  "optionally

substituted  alkyl  group"  represented  by  R12   or  RD  incl~de

15    the same groups as the "alkyl group" or the "substituted alkyl group" represented by the aforementioned R1 • Among them, a methyl group and an ethyl group are preferable.

Examples of the "acyl group" represented by R12 or R13 include an alkylcarbonyl group, and an arylcarbonyl group.

20    Examples of the alkylcarbonyl group include a (C1~C6 alkyl)carbonyl group, preferably a (Cl-C4 alkyl)carbonyl group such as an acetyl group, a trifluoroacety~ group, a propionyl group, and a butyryl group. Examples of the
 
arylcarbonyl group include a (C6-C14 aryl)carbonyl group such as a benzoyl group, and a naphthoyl group.

Examples of the "alkylthio group", "alkylsulfinyl group", "alkylsulfonyl group" and "optionally substituted

5    amino group" represented by R12 or R13 include those referred to as R1 •


Examples of the "cycloalkyl group" represented by R12 or R13 include a cycloalkyl group having 3 to 7, preferably 5 to 6 carbon atoms, specifically, a cyclopropyl group, a

10    cyclobutyl group, a cyclopentyl group, a cyclohexyl group, and a cycloheptyl group.


Examples  of  the  "optionally  substituted  aryl  group"

represented by R12 or R13 include a C6-C14 aryl group, specifically, a phenyl group, a naphthyl group (1-naphthyl

15    group}, and a fluorenyl group. Among them, a phenyl group is preferable.



The aryl group may be substituted at any possible position of the ring thereof, and the number of substituents is 1 to 3. Examples of the substituent

20    include a halogen atom, an optionally substituted alkyl group, an optionally substituted hydroxy group, an alkylthio group, an optionally substituted.amino group, a nitro group, a phenyl group, and a cyano group.


Examples  of  the  halogen  atom  as  the  substituent  of  the

25    "optionally  substituted  aryl  group"  represented  by  R12  or
 
R13 include fluorine, chlorine, bromine, and iodine. Examples of the optionally substituted alkyl group as

the  substiuent  of  the  "optionally  substituted  aryl  group"

represented  by  R12   or  R13   include  the  same  group  as  the

5    "optionally substituted alkyl •group" represented by R1 • Among them, an alkyl group or a haloalkyl group is
preferable,    and  a  methyl  group  or  a  trifluoromethyl  group

is  particularly  preferable.

Examples  of  the  optionally  substituted  hydroxy  group

10    as the substituent of the "optionally substituted aryl group" represented by R12 or R13 include a hydroxy group, an alkoxy group, an alkenyloxy group, an alkynyloxy group, a

haloalkoxy  group,   and  an  aryloxy  group.

Examples  of  the  alkoxy  group  include  an  alkoxy  group

15    having 1 to 8, preferably 1 to 4 carbon atoms, specifically, a methoxy group, an ethoxy group, a •propoxy group, and a butoxy group. Among them, a methoxy group is preferable.

Examples of the alkenyloxy group include an alkenyloxy group having 2 to 8, preferably 2 to 4 carbon atoms,
20    specifically, a vinyloxy group, an allyloxy group, and a crotyloxy group. Among them, an allyloxy group is

preferable.

Examples of the alkynyloxy group include an alkynyloxy group having 2 to 8, preferably 2 to 4 carbon atoms,

25    specifically,   an  ethynyloxy  group,   a  propargyloxy  group,
 
and  a  butynyloxy  group.    Among  them,   a  propargyloxy  group

is  preferable.

Examples  of  the  haloalkoxy  group  include  the

aforementioned  alkoxy  group  substituted  with  at  least  one

5    halogen atom (e.g. fluorine, chlorine, bromine, iodine), specifically, a difluoromethoxy group, a trifluoromethyl group, and a chloromethoxy group. Among them, a difluoromethoxy group is preferable.

Examples  of  the  aryloxy  group  include  an  aryloxy  group

10    having 6 to 12, preferably 6 to 8 carbon atoms, specifically, a phenoxy group, and a naphthoxy group.

Examples  of  the  alkylthio  group  as  the  substituent  of

the  "optionally  substituted  aryl  group"  represented  by  Ru

    or  R13   include  an  alkylthio  group  having  1  to  8,  preferably   
15    1  to  4,   further  preferably  1  to  2  carbon  atoms.   
    Examples  of  such  alkylthio  group  include,   specifically,   
    a  methylthio  group,   an  ethylthio  group,   a  propylthio  group,   
    and  a  butylthio_group.Among  them,   a  methylthio  group  is   
    preferable.                                       
20    Examples        of  the    optionally    substituted  amino  group  as   
    the  substituent  of  the  "optionally  substituted  aryl  group''   
    . d  b    y    R12    or    R13   '    1    u    d    e    '   
    represente                ~nc                    an  am~no group,   and  an   

amino group mono- or di-substitu~ed with an alkyl group having 1 to 8, preferably 1 to 4 carbon atoms (e.g.

25    monomethylamino  group,   dimethylamino  group,  or
 
monoethylamino  group) .

Examples  of  the  "optionally  substituted  heterocyclic

group" represented• by R12 or R13 include a heterocyclic group containing 1 to 4, preferably 1 to 2 hetero atoms

5 (e.g. oxygen, nitrogen, sulfur) in a ring. These heterocyclic groups may have a bond at any possible position of the ring. Examples of the heterocyclic group

include a pyridyl group, a pyridazinyl group, a pyrazolyl group, a pyrimidinyl group, a furyl group, a thienyl group,

10    an oxazolyl group, an isoxazolyl group, a benzothiazolyl group, a quinolyl group, a quinazolinyl group, a pyraziny~ group, a morpholino group, and a piperazinyl group. Among

them,    a  furyl  group   (e.g.   2-furyl  group),  a  thienyl  group

(e.g.  2-thienyl  group),   a  pyridyl  group   (e.g.   2-pyridyl

15    group), a pyrazinyl group (e.g. 2-pyrazinyl group), a pyrimidinyl group (e.g. 2-pyrimidinyl group), and a morpholino group are preferable. The heterocyclic group may be substituted, and examples of the substituent include


the  same  group  as  the  substituent  of  the  "optionally

20    substituted  aryl  group"  represented  by  R12 •  or  R13 •

The  "monocycle  or  polycycle  formed  by  binding  of  R12

or  R13 ,    optionally  containing  'a  hetero  atom"  is  a  4-  to  8-

membered  ring  option~lly containing  a  he.tero  atc;>m   (e.g.

oxygen,    nitrogen,   sulfur),  which  is  formed  by  R12   or  R13

25    together  with  a  carbon  atom  to  which  they  bind.    The  ring
 

18

may form a fused ring with another ring. Examples of the ring include cyclopentane, cyclohexane, indane, 1,2,3,4-tetrahydronaphthalene, 5,6,7,8-tetrahydroquinoline, and 4,5,6,7-tetrahydrobenzo[b]furan. These rings may have a


5    divalent  bond  at  any  possible  position  thereof.

Examples  of  the  alkyl  group  of  the'"optionally

substituted  alkyl  group"  represented  by  Q include  the  alkyl

group  represented  by  the  aforementioned  R1 •

Examples  of  the  alkyeyl  group  of  the  "optionally

10    substituted alkenyl group" represented by Q include an alkenyl group having 2 to 8, preferably 3 to 6 carbon atoms, specifically, an allyl group, a propenyl group, an

isopropenyl group, a butenyl group, an isobuteyl group, a pentenyl group, a hexenyl group, and a hexadienyl group.

15    Examples  of  the  alkynyl  group  of  the  "optionally

substituted alkynyl group" represented by Q include an alkynyl group having 2 to 6, preferably 2 to 4 carbon atoms, specifically, a propargyl group, an ethynyl group, and a butynyl group. Examples of tpe substituent when these


20    alkyl group, alkenyl group, and alkynyl group are substituted include a halogen atom, an alkoxy group, an

alkylthio group, an alkylsulfinyl group, an alkylsulfonyl group, and an substituted amino group, each being referred
to  as  R1 ,   as  well  as  an  optionally  substituted  phenyl  group,

25    an  •optionally  substituted  naphthly  group,  an4  an  optionally
 

    19
    substituted  heterocyclic  group,   each  being  referred  to  as  Q.
    Examples  of  the  '~substituted carbonyl  group"
    represented •by  Q  include  an  alkylcarbonyl  group,   a
    phenylcarbonyl  group,   a  naphthylcarbonyl  group,   and  a
5    carbonyl  group  bonded  with  a  heterocyclic  group.
    Examples  of  the  "substituted  sulfonyl  group"
    represented  by  Q  include  an  alkylsulfonyl  group,   a
    phenylsulfonyl  group,   a  naphthylsulfonyl  group,   and  a
    sulfonyl  group  bonded  with  a  heterocyclic  group.
10    The  substituent  in  the  "substituted  sulfonyl  group"
    and  the  "substituted  carbonyl  group"  may  further  have
    substituent(s).For  example,   each  a+kyl  group  in  the
    alkylcarbonyl  group  and  the  alkylsulfonyl  group  may  be
    substituted.
15    Examples  of  the  substituent  in  the  "substituted
    carbonyl  group"  and  the  "substituted  sulfonyl  group"
    represented  by  Q  include  an  optionally  substituted  alkyl
    group,   an  optionally  substituted  phenyl  group,   an
    optionally  substituted  naphthyl  group,   and  an  optionally
20    substituted  heterocyclic  group.
    Examples  of  the  "optionally  substituted  alkyl  group"
    in  the  "substituted  carbonyl  group"  or  the  "substituted
    sulfonyl  group"  include  those  referred  to  as  R1 •
    Examples  of  the  optionally  substituted  phenyl  group,
25    the  optionally  substituted  naphthyl  group,   and  the

optionally  substituted  heterocyclic  group  in  the

"sub~tituted carbonyl group" or the "substituted sulfonyl group" include those referred to as Q, respectively.
In  the  present  invention,   Q  is  preferably  an

5    optionally substituted phenyl group, more preferably a phenyl group optionally substituted with a halogen atom, a methyl group, a trifluoromethyl group or a methoxy group, further preferably a phenyl group, a 2-methylphenyl group, or a 2,5-dimethylphenyl group, particularly preferably a


10    2,5-dimethylphenyl  group.

X represents a hydrogen atom, a halogen atom, an optionally substituted alkyl group, or an optionally-substituted hydroxy group. That is, a phenylene group in the formula (II) may be unsubstituted (when X is a hydrogen


15    atom), or may be substituted at any position with a substituent selected from a halogen atom, an optionally substituted alkyl group and an optionally substituted

hydroxy  group.

Examples  of  the  "halogen  atomn  or  the  "optionally

20    substituted alkyl group" represented by X include those referred to as R1 .



Examples of the "optionally substituted hydroxy group" represented by X include a hydroxy group, an optionally substituted alkoxy group, an optionally substituted

25    alkenyloxy  group,   an  optionally  substituted  alkynyloxy
 

    21
    group,   an  alkylcarbonyloxy  group,   an   (alkylthio)carbony~oxy
    group,   an  alkylsulfonyloxy  group,   an  arylsulfonyloxy  group,
    a  mono-  or  di-alkyl-substituted  carbamoyloxy  group,  an
    aryloxy  group,   and  a  tetrahydropyranyloxy  group.
5    Examples  of  the  substituent  of  the  "optionally
    substituted  hydroxy  group"  include  an  alkyl  group,   an
    alkenyl  group,   an  alkynyl  group,   an   (alkylthio)carbonyl

group, an alkylcarbonyl group, an alkylsulfonyl group, an arylsulfonyl group, a mono- or di-alkyl-substituted

10    carbamoyl group, an aryl group, and a tetrahydropyranyl group. Among these groups, an alkyl group, an alkenyl group and an alkynyl group may be substituted with a

halogen atom (e.g. fluorine, chlorine, bromine, iodine, preferably fluorine), or an alkoxy group having 1 to 8,

15    preferably  1  to  4  carbon  atoms.

X  is  preferably  a  hydrogen  atom.

Examples of the '.'optionally substituted hydroxy group" represented by Y include those referred to as X.

Examples  of  the  "alkylthio  group"  represented  by  Y

20    include  those  referred  to  as  R1 •

The "optionally.substituted amino group" represented by Y is represented, for example, by the formula (III):

(I~I)

wherein  R5   represents  a  hydrogen  atom  or  an  alkyl  group;  R6

25    represents  a  hydrogen  atom,   an  alkyl  group  or  a


hydroxylalkyl  group.

Examples  of  the  "alkyl  group"  represented  by  R5   or  R6 ,

and  the  "alkyl  group"  of  the  "hydroxylalkyl  group"

represented  by  R 6   include  those  referred  to  as  R1 •

5    Preferably,.R5   an~ R6 ,    which  are  the  same  or  different,   are

a hydrogen atom or an alkyl group (preferably methyl group) . Examples of Y include preferably a. Cl-C3 alkoxy group

and a group represented by the formula (III), further preferably a methoxy group or a mono Cl-C3 alkylamine group

10    (preferably,  monomethylamino  group).

z is  preferably  an  oxygen  atom.

M is  preferably  an  oxygen  atQm,   a  sulfur  atom  or  N~2

(R2 represents a hydrogen atom, an alkyl group or an acyl group), further preferably an oxygen atom.
15    Examples  of  the  "alkyl  group"  represented  by  R2

include  those  referred  to  as  R1 •

Among  them,   a  methyl  group  is  preferable.

Examples  of  the  "acyl  groupn  represented  by  R2   include

a    formyl  group;   an  alkylcarbonyl  group  containing  an  ~lkyl

20    group having 1 to 8, preferably 1 to 4 carbon atoms (e.g. acetyl group, propionyl group, butyryl group); a benzoyl

group.

Among  them,   an  acetyl  group  is  preferable.

n is  preferably  0  or  1,  more  preferably  1.

25    In  the  present  invention,   the  preferable  compound  II
 
is    represented  by  the  formula   (II),   wherein,

R1 is a halogen atom, a Cl-C4 alkoxy group, or a Cl-C4 haloalkoxy group,



Q  is  a  phenyl  group  optionally  substituted  with  at

5    least one substituent selected from the group consisting of a halogen atom, a methyl group~ a trifluoromethyl group and

a  methoxy  group,

X is  a  hydrogen  atom,

Y  is  an  amino  group  optionally  substituted  with  at

10    least  one  Cl-C3  alkyl  group,   or  a  Cl-C4  alkoxy  group,

Z is  an  oxygen  atom,

M is  an  oxygen  atom,   and

n  is  an  integer  of  1.

A more preferable compound is represented by the 15 formula (II), wherein,


R1 is a methoxy group, an ethoxy group or a difluoromethoxy group,
Q is a phenyl group, a 2-methylphenyl group or a 2,5-dimethylphenyl group,

20    X is  a  hydrogen  atom,

Y is  a  methylamine  group  or  a  methoxy  group,

Z is  an  oxygen  atom,

M is  an  oxygen  atom,   and

n  is  an  integer  of  1.

25    A  further  preferable  compound  is  represented  by  the
 

24

formula    (II),  wherein,

R1   is  a  methoxy  group,

Q  is  a  2,5-dimethylphenyl  group,

X  is  a  hydrogen  atom,
5    y  is  a  methylamino  group,

z is  an  oxygen  atom,

M is  an  oxygen  atom,   and

n    is  an  integer  of  1.

Each  of  the  compound  represented  by  the  formula   (II)

10    and an agrochemically acceptable salt thereof includes one or more kinds of stereoisomers such as an optical isomer, and a geometric isomer based on an asymmetric carbon atom

and a double bond, in some cases. Such isomers and a mixture thereof all fall within the scope of the present

15    invention.

Some of the compound represented by the formula (II) and an agrochemically acceptable salt thereof take forms of solvates (e.g. hydrate). These forms fall within the scope of the present invention.


•20    Some  of  the  compound  represented  by  the  formula   (II)

and a salt thereof take crystal forms and/or amorphous forms, and these forms fall within the scope of the present invention.

Hereinafter, among the compound II, the compound II - i 25 has a.R-type steric structure according to Cahn Ingold- •

Prelog rule, wherein R1 is a methoxy group, X is a hydrogen atom, Y is a methylamino group, Z is an oxygen atom, M is

an oxygen atom, Q is a 2,5-dimethylphenyl group, and n is an integer of 1, which is represented by the following

5    formula   (IIa)  .

In  addition,   among  the  compound  II,   the  compound  II - ii

is  a  racemate,  wherein  R1   is  a  methoxy  group,  X  is  a

nydrogen  atom,  Y  is  a  methylamino  group,   z• is  an  oxygen

10    atom, M is an oxygen atom, Q is a 2,5-dimethylphenyl group, and n is an integer of 1, which is represented by the following formula (IIb) .

In  the  present  composition,   in  addition  to  the

1•5 compound (I) and the compound A, a compound which inhibits an electron transport complex III such as fluoxastrobin ((E)-{2-[6-(2-chlorophenoxy)-5-fluoropyrimidin-4-
 
yloxy]phenyl} (5,6-dihydro-1,4,2-dioxadin-3-yl)methanone 0-methyloxime), metominostrobin ((E)-2-methoxyimino-N-methyl-2-{2-phenoxyphenyl)acetamide), and pyribencarb may be added as far as it does not adversely affect the characteristics


5    of  the  present •invention.

The present invention can be used for farmlands, i . e . , cropland, or non-farmlands such as dry field, paddy field, turf and fruit orchard. In addition, the present invention can be used for controlling diseases of »crops" such as


10    those listed below without giving phytotoxicity to the crops.


Agricultural  crops:  corn,   rice,  wheat,  barley,   rye,

oat, sorghum, cotton, soybean, peanut, buckwheat, sugar beet, rapeseed, sunflower, sugar cane, and tobacco;
15    Veget~bles: Solanaceae  vegetables   {e.g.  eggplant,


tomato,    green  pepper,  hot  pepper,   and  potato),

Cucurbi taceae vegetables (e.g. cucumber, pumpkin, zucchi.ni, watermelon, and melon), Cruciferae vegetables (e.g. Japanese radish, turnip, horseradish, kohlrabi, Chinese

20    cabbage, cabbage, brown mustard, broccoli, and cauliflower), Compositae vegetables (e.g. burdock, garland chrysanthemum, artichoke, and lettuce), Liliaceae vegetables (e.g. Welsh
 

onion, onion, garlic, and asparagus), Dmbelliferae vegetables (e.g. carrot, parsley, celery, and parsnip),

25    Chenopodiaceae  vegetables   (e.g.   spinach,  and  Swiss  chard),
 

        27
    Labiatae  vegetables   (e.g.  Japanese  basil,  mint,   and  basil),
    strawberry,   sweat  potato,  yam,   and    aroid;
    Flowers    and  ornamental  plants;
    Foliage    plant;
5    Fruit  trees:   pomaceous  fruits   (e.g ..  apple,   common  pear,
    Japanese  pear,   Chinese  quince,   and  quince),   stone  fleshy
    fruits   (e.g.   peach,  plum,  nectarine,   Japanese  plum,   cherry,

apricot, and prune), citrus plants (e.g. Satsuma mandarin, orange, lemon, lime, and grapefruit), nuts (e.g. chestnut,

10    walnut, hazel nut, almond, pistachio, cashew nut, and macadamia nut), berry fruits (e.g. blueberry, cranberry, blackberry, and raspberry), grape, persimmon, olive, loquat,

banana,    coffee,   date,   and  coconut;

Trees  other  than  fruit  trees:   tea,  mulberry,   flowering

15    trees and shrubs, street trees (e.g. ash tree, birch, dogwood, eucalyptus, ginkgo, lilac, maple tree, oak, poplar, cercis, Chinese sweet gum, plane tree, zelkova, Japanese arborvitae, fir tree, Japanese hemlock, needle juniper,


    pine,   spruce,   and  yew).
20    The  above  "crops"  include  those  having  herbicide
    resistance  imparted  by  a  classical  breeding  method,   or  a
    genetic  engineering  technique.Examples  of  the  herbicide
    to  be  resisted  include  an  HPPD  inhibitor  such  as
    isoxaflutole,   an  ALS  inhibitor  such  as  imazethapyr  or
25    thifensulfuron-methyl;   an  EPSP  synthesizing  enzyme

inhibitor; and a glutamine synthesizing enzyme inhibitor; bromoxynil.
Examples of the "crops" having herbicide resistance imparted by a classical breeding method include

5 Clearfield~ canola resistant to an imidazolinone herbicide such as imazethapyr, and STS soybean resistant to a sulfonylurea ALS inhibitor-type herbicide such as thifensulfuron-methyl. Examples of the ncrops" having herbicide resistance imparted by a genetic engineering

10    technique include soybean, cotton, and rapeseed cultivars having resistance to glyphosate or glufosinate. Some of such corn cultivars have been already marketed under the

trade  name  of  RoundupReady™,    and  LibertyLink™.

The  above  "crops"  include  those  having  an  ability  to

15    ~ynthesize,  for  example,   a  selective  toxin  such  as  that

derived from the genus Bacillus which ability has been imparted by a genetic engineering technique.

Examples of the ~oxin expressed by such a genetically modified plant include insecticidal proteins derived from

20    Bacillus cereus and•Bacillus popilliae; o-endotoxins derived from Bacillus thuringiensis such as Cry1Ab, Cry1Ac,

CrylF,    Cry1Fa2,   Cry2Ab,   Cry3A,   Cry3Bb1  and  Cry9C;

insecticidal proteins derived from Bacillus thuringiensis, such as VIP 1, VIP 2, VIP 3 and VIP 3A; insecticidal
25    proteins  derived  from  nematodes;   toxins  produced  by  animals

such as scorpion toxins, spider toxins, bee toxins and insect-specific nerve toxins; fungal toxins; plant lectin; agglutinin; protease inhibitors such as trypsin inhibitors, serine protease inhibitors, patatin, cystatin, and papain


5    inhibitors; ribosome-inactivating-proteins (RIP) such as ricin, corn-RIP, abrin, saporin, and briodin; steroid metabolizing enzymes such as 3-hydroxysteroid oxidase,

ecdysteroid-UDP-glucosyltransferase,   and  cholesterol

oxidase;    ecdysone  inhibitors;  HMG-CoA  reductase;  ion

10    channel inhibitors such as sodium channel inhibitors and calcium channel inhibitors; juvenile hormone esterase; diuretic hormone receptors; stilbene synthase; bibenzyl syntase; chitinase; and glucanase.


The  insecticidal  toxin  produced  by  such  a  genetically

15    modified plant also includes hybrid toxins of 2 or more insecticidal proteins, and toxins in wtich a part of amino acids constituting an insecticidal protein is deleted or

modified.    The  hybrid  toxin  is  made  by  a  new  combination  of

different  domains  of  the  insecticidal  proteins  by  a  genetic

20    engineering technique. An example of the toxin in which a part of amino acids constituting an insecticidal protein is deleted includes Cry1Ab in which a part of amino acids is deleted. An example of the toxin in which a part of amino acids constituting an insecticidal protein is modified
 


25    •includes  a  toxin  in  which  one  or  more  of  amino  acids  of  a
 

30

natural  toxin  are  substituted.

Example~ of these toxins and recombinant plants capable of synthesizing these toxins are described in EP-A-0 374 753, WO 93/07278, WO 95/34656, EP-A-0 427 529, EP-A-

5    451  878,   and  WO  03/052073.

Toxins contained in these recombinant plants gives the plants resistant to, particularly, Coleoptera pests, Diptera pests, or Lepidoptera pests.

Jn  addition,   gen~tically modified  plants  containing

10    one or plural insecticidal pest-resistant genes and expressing one or plural toxins have been already known, and some of them are commercially available. Examples of

these  genetically  modified  plants  include  YieldGard™    (corn

variety  expressing  Cry1Ab  toxin),   YieldGard  Rootworm™

15    (corn variety expressing Cry3Bbl toxin), YieldGard Plus™ (corn variety expressing CrylAb and Cry3Bbl toxins),
Herculex  r™    (corn  variety  expressing  phosphinothricin  N-

acetyltransferase    (PAT)   for  imparting  resistance  to  Cry1Fa2

toxin  and  glufosinate),   NuCOTN33B   (cotton  variety

20    expressing CrylAc toxin), Bollgard I™ (cotto~ variety expressing CrylAc toxin), Bollgard II™ (cotton .variety expressing CrylAc and Cry2Ab toxins), VIPCOT™ (cotton

variety  expressing  VIP  toxin) ,  NewLeaf™    (potato  variety

expressing  Cry3A  toxin),  NatureGard™,    Agrisure™    GT

25    Advantage   (GA21  glyphosate  resistance  character),

Agrisure™ CB Advantage (Bt11 corn borer (CB) character) , and Protecta™.



The above "crops" also include those to which the ability to produce an anti-pathogenic substance having

5    selective activity has been imparted by a'genetic engineering technique.



As examples of the anti-pathogenic substance, a PR protein is known (PRPs, EP-A-0 392 225) . Such an anti-pathogenic substance and a genetically modified plant

10    producing the same are described in EP-A-0 392 225, WO 95/33818, and EP-A-0 353 191.

Examples  of  the  anti-pathogenic  substance  expressed  in

such  the  genetically  modified  plant  include  ion  channel

inhibitors    such  as  sodium  channel  inhibitor,   and  calcium

15    channel inhibitor (KPl, KP4, KP6 toxins produced by viruses are known); stilbene cynthase; bibenzyl cynthase;

chitinase;    glucanase;  ER  protein;   anti-pathog~nic

substances  produced  by  microorganisms  such  as  peptide

antibiotics,    heterocycle-containing  antibiotics,   and

20    protein factors involved in plant disease-resistance (described in WO 03/000906) .

Examples  of  plant  diseases  which  can  be  controlled  by

the  present  invention  are  not  limited  to,  but  include  the

plants  and  diseases  thereof  as  follows.

25    Rice:   rice  blast   (Magnaporthe  grisea),   spot  leaf  blight

(Cochliobolus  miyabeanus),   sheath  blight   {Rhizoctonia

solani),    silly  seedling   (Gibberella   fujikuroi);

Wheat,    barley,   etc . :  powdery  mildew   {Erysiphe  graminis),

red  mold   {Fusarium  graminearum,  F.   avenacerum,  F.   culmorum,

5    Microdochium nivale), rust (Puccinia striiformis, P. graminis, P. recondita, P. hordei), snow mold (Typhula sp.,

Micronectriella nivalis), loose smut (Ustilago tritici, U. nuda), bunt (Tilletia•caries), eyespot (Pseudocercosporella
herpotrichoides),    scald  disease   (Rhynchosporium  secalis),

10    leaf blight (Septaria tritici), spot blight (Leptosphaeria nodorum), net blotch (Pyrenophora teres Drechsler);
Citrus  fruits:   black  spot  disease   (Diaporthe  citri),   scab

(Elsinoe  fawcetti),   fruit  rot   (Penicillium  digitatum,   P.

italicum);

15    Apple:  blossom  blight   (Monilinia  mali),   decomposed  disease

(Valsa  ceratosperma),  powdery  mildew   (Podosphaera

leucotricha),    Alternaria  blotch   (Alternaria  alternata  apple

pathotype),    scab   (Venturia  inaequalis),   anthrax

(Colletotrichum  acutatum),   crown  rot   {Phytophtora

20    cactorum);

Pear:   scab   {Venturia  nashicola,  V.  pirina),  purple  blotch

(Alternaria  alternata  Japanese  pear  pathotype),   frogeye

(Gymnosporangium  haraeanum),   fruit  rot   (Phytophtora

cactorum);

25    Peach:  brow~ rot   (Monilinia•fructicola),   black  spot  disease

(Cladosporium    carpophilum).,   Phomopsis  rot   (Phomopsis  sp.);

Grape:    eastern  black  disease   (Elsinoe  ampelina),   nights

grapes  rot   (Glomerella  cingulata),  powdery  mildew   (Uncinula

necator),    rust   (Phakopsora  ampelopsidis),   black  rot

5    (Guignardia  bidwellii),   downy  mildew   (Plasmopara  viticola);

Persimmon:    anthracnose   (Gloeosporium  kaki),   brown  stem  rot

(Cercospora  kaki,   Mycosphaerella  nawae);

Cucurbit:    anthracnose   (Colletotrichum  lagenarium),  powdery

mildew    (Sphaerotheca   fuliginea),   vine  blight

10    (Mycosphaerella  melonis),   yellow  vine  disease   (Fusarium

oxysporum),    mildew   (Pseudoperonospora  cubensis),

Phytophtora  rot   (Phytophthora  sp.),   seedling  damping-off

(.Pythium  sp.) ;

Tomato: ring spot disease (Alternaria solani), leaf mold 15 (Cladosporium fulvum), late blight (Phytophthora

infestans) ;

Eggplant: brown spot disease (Phomopsis vexans), powdery mildew (Erysiphe cichoracearum);

Cruciferous  vegetable:  black  spot  disease   (Alternaria

20    japonica),  vitiligo   (Cercosporella  brassicae),.clubroot

(Plasmodiophora  brassicae),  •mildew   (Peronospora

parasitica);

Leek  rust   (Puccinia  allii),   soybean  purpura   (Cercospora

kikuchii),    eastern  black  disease   (Elsinoe  glycines),  black

25    spot  disease•  (Diaporthe  phaseolorum  var.   sojae),   rust
 
(Phakopsora pachyrhizi), plaque stalks (Phytophthora sojae), bean anthracnose (Colletotrichum lindemthianum), peanut black mildew (Cercospora personata), brown spot disease

(Cercospora    arachidicola),  blight   (Sclerotium  rolfsii);

5    Pea:  powdery  mildew   (Erysiphe  pisi);

Potato:   early  blight   (Alternaria  solani),   late  blight

(Phytophthora infestans), powder scab (Spongospora subterranean f. sp. subterranea);
Strawberry:    powdery  mildew   (Sphaerotheca  humuli);

10    Tea: net rice disease (Exobasidium reticulatum), disease victory (Elsinoe leucospila), ring leaf spot

(Pestalotiopsis  sp.),   anthracnose   (Colletotrichum  theae-

sinensis) ;

Tabaco:    frogeye   (Alternaria  longipes),  powdery  mildew

15    (Erysiphe  cichoracearum),   anthracnose   (Colletotrichum

tabacum),    mildew   (Peronospora  tabacina),  black  shank

(Phytophthora  nicotianae);

Sugarbeet:  brown  spot   (Cercospora  beticola),   leaf  rot

(Thanatephorus    cucumeris),   root  rot   (Thanatephorus

20    cucumeris),  black  root  rot   (Aphanidermatum  cochlioides);

Rose:  black  spot   (Diplocarpon  rosae),   powdery  mildew

(Sphaerotheca  pannosa);

Chrysanthemum: brown spot (Septaria chrysant_hemi-indici), white rust (Puccinia horiana);
 

25    Diseases  caused  by  the  genus  Pythium  of  various  crops
 

35

(Pythium aphanidermatum, Pyt~ium debarianum, Pythium graminicola, Pythium irregulare, Pythium ultimum), gray mold (Botrytis cinerea), white mold, Sclerotinia rot, stem, rot, crown rot (Sclerotinia sclerotiorum, Sclerotinia


5    minor);

Radish:  black  spot  disease   (Alternaria  brassicicola);

Turfgrass: dollar spot disease (Sclerotinia homeocarpa), brown patch disease and large patch disease (Rhizoctonia solani);

•    10 Banana: Sigatoka disease (Mycosphaerella fijiensis, Mycosphaerella musicola,. Pseudocercospora musae) .
The  present  invention  exhibits  a  particularly  high

effect on gray mold, white mold, Sclerotinia rot, stem rot, crown rot, brown rot,. blossom blight, eyespot, and scald

15 disease of various crops, among the above plant diseases. The weight ratio of the compound A and the compound I

contained in the present composition of the invention is usually 0.025 : 1 to 20 1, preferably 0.05 : 1 to 5 : 1, further preferably 0.05 1 to 0.25 : 1 (compound A

20    compound  I) .

The present composition may consis•t in compound A and the compound I without addition of any other ingredients, or may form a formulation in the form of a solid or liquid formulation such as wettable powder, granulated wettable


25    powder,  flowable,   granules,   dry  flowable,   emulsifiable

concentrate, aqueous liquid formulation, oil solution, smoking pesticide, and aerosol, microcapsules.

Usually, these formulations can contain 0.1 to 99% by weight, preferably 0.2 to 90% by weight of the compound A

5    and  the  compound  I   in  total.

These formulations can be prepared, for example, by mixing'the compound A and the compound I with a solid carrier, a liquid carrier, a gas carrier, and a surfactant and, if necessary, adding auxiliary agents for formulations


10 such as a binder, a d~spersant, and a stabilizer. Examples of the solid carrier include finely divided

powders and particles of clays (e.g. kaolin, diatomaceous earth, synthetic •hydrous silicon oxide, Fubasami clay, bentonite, or acid clay), tales, other inorganic minerals

15 (e.g. sericite, quartz powder, sulfur powder, active carbon, calcium carbonate, or hydrated silica), and the like. Examples of the liquid carrier include water, alcohols (e.g. methanol, or ethanol), ketones (e.g. acetone, or methyl ethyl ketone), aromatic hydrocarbons (e.g. benzene, toluene,


20    xylene, ethylbenzene, or methylnaphthalene), aliphatic hydrocarbons (e.g. n-hexane, cylcohexanone, or kerosene),

esters (e.g. ethyl acetate, or butyl acetate), nitriles (e.g. acetonitrile, or isobutylonitrile), ethers (e.g.• dioxane, or diisopropyl ether), acid amides (e.g.

25    dimethylformamide,   or  dimethylacetamide) ,  and  halogenated
 

37
hydrocarbons    (e.g.   dichloroethane,   trichloroethylene,   or

carbon  tetrachloride) .

Examples  of  the  surfactant  include  alkylsulfates,

alkylsulfonates,    alkylarylsulfonates,   alkyl  aryl  ethers  and

5    polyoxyethylenated compounds thereof, polyoxyethylene glycol ethers, polyhydric alcohol esters, and sugar alcohol

derivatives.

Examples  of  other  auxiliary  agents  for  formulations

include  a  binder  and  a  dispersant,   specifically,   casein,

10    gelatin,  polysaccharides   (e.g.   starch,   gum  arabic,

cellulose derivatives, or alginic acid), lignin derivatives, bentonite, sugars, synthetic water-soluble polymers (e.g.

polyvinyl alcohol, or polyvinylpyrrolidone, polyacrylic acids), PAP (acidic isopropyl phosphate), BHT (2,6-di-tert-

15    butyl-4-methylphenol) , BHA (mixture of 2-tert-butyl-4-methoxyphenol and 3-tert-butyl-4-methoxyphenol), vegetable oils, mineral oils, and fatty acids and esters thereof ..

The present composition can also be prepared, for example, by separately formulating the compound A and the

20    compound I into different formulations by the above procedures, if 'necessary, further diluting each of• them

with water, thereafter, mixing separately prepared different formulations and dilute solutions.

In  the  present  controlling  method,   respective

25    compounds  may  be  applied  to  a  plant,   a  seed  of  a  plant  or  a
 

38
land where the plant is grown, simultaneously or separately. In the present controlling method, when the compound A

and the compound I are simultaneously applied to a plant, a seed of a plant or a cropland, the present composition can

5    be  applied,   for  example,  by  the  following  method.

The method of applying the present composition is not particularly limited, as far as the present composition can be substantially applied, and examples thereof include treatment of a plant such as foliage spraying, treatment of


10    a land such as soil treatment, and treatment of a seed such as seed disinfection.



While the application amount of the present composition differs depending on various conditions such as

a  particular  con~ent ratio  of  the  compound  A  and  the

15    compound I, weather conditions, formulation form, application period, application method, application place, and subject disease, subject crop, the total amount of the compound A and the compound I in the soil treatment is

usually  1  to  500  g,  preferably  2  to  200  g  per  1000  m2 •

20    When  the  present  composition  is  in  the  form  of  an

emulsifiable concentrate, wettable powder, suspension, or the like, it is usually applied after diluting with water, and the concentration thereof is usually 0.0005 to 2% by weight, preferably 0.005 to 1% by weight of the compound A


25    and  the  compound  I   in  total.    When  the  present  composition

is in the form of dust, granules or the like, it is usuallj applied as it is without dilution.



The above application amount in treatment of a seed iE in the range of usually 0.001 to 10 g, preferably 0.01 to 1

5    g of the compound A and the compound I in total relative tc 1 kg of a seed.



Further, in the present controlling method, when the compound A and the compound I are separately applied to a plant, a seed of a plant, or a cropland, both compounds may

10    be separately applied, for example, by the above methods, and.the application order of both compounds is•not limited. Application methods of both compounds may be the same or different. The interval of applications between both of them is, however, preferably shorter, and desirably within


15    one  day.

The application amount of each compound differs depending on various conditions such as a particular application amount ratio of the compound A and the compound I, weather conditions, formulation form, application period


20    application method, application place, and subject disease, subject crop and, the total amount of the compound (A) and the compound I in the soil treatment is usually 1 to 500 g,
preferably  2  to  200  g  per  1000  m2 •

The weight ratio of the compound A and the compound I 25 to be applied separately is usually 0.125 : 1 to 20 : 1,
 

40

preferably 0.25 1 to 10 1 (the compound A the compound I) .



When both compounds are in the form of emulsifiable concentrates, wettable powders, suspensions, or the like,
5    the concentration of each compound upon application is usually 0.0005 to 1% by weight, preferably 0.005 to 0.5% by weight, respectively, and when each compound is in the form of dust, granules or the like, it is usually applied as it is without dilution. In treatment of a seed, each of the


10    compound A and the compound I is applied in the range of usually 0.001 to 5 g, preferably 0.01 to 0.5 g relative to
1  kg  of  a  seed.

Furthermore, the present composition can be used simultaneously with one. or more fungicides, insecticides,

15    miticides, nematocides, herbicides, plant growth regulating agents, fertilizers or soil improvers by mixing with them

or  without  mixing  them.

The fungicides, insecticides, miticides, nematocides, herbicides, plant growth regulating agents, fertilizers or

20    soil  improvers  described  above  can  be  the  known  ones.

Hereinafter~ the present invention will be explained in more detail by the following Formulation Examples, Test

Examples and Comp~rative Examples, but the present invention is not limited to the following Examples•.• • In the

25    following  Examples,   all  the  "parts"  are  by  weight  unless
otherwise stated. The compound II - i and the compound II - ii are as defined above. The cqmpound III represents dimoxystrobin, the compound IV represents trifloxystrobin, the compound V represents azoxystrobin, and the compound VI


5 represents pyraclostrobin. Formulation Example 1

Three parts of the compound I, 2 parts of the compound II - i, the compound II - ii, the compound III, the compound IV, the compound V or the compound VI, 14 parts of

10    polyoxyethylene •styryl phenyl ether, 6 parts of calcium dodecylbenzenesulfonate and 75 parts of xylene are thoroughly mixed to prepare each emulsifiable concentrate.

Formulation  Example  2

Five  parts  of  the  compound  I,   5  parts  of  the  compound

15    II - i, the compound II - ii, the compound III, the compound IV, the compound V or the compound VI, 35 parts of a mixture of white carbon and a polyoxyethylene alkyl ether sulfate ammonium salt (weight ratio 1 •= 1) and 55 parts of water


are  mixed,   and  pulverized  by  a  wet  grinding  method  to

20 prepare each flowable. Formulation Example 3

Twenty parts of compound I, 1 part of the compound II-i, the compound II - ii, the compound III, the compound IV, the compound V or the compound VI, and 28.5 parts of an

25    aqueous  solution  containing  1.5  parts  of  sorbitan  trioleate
 
42

and 2 parts of polyvinyl alcohol are mixed, and pulveriz~d by a wet grinding method, 37.35 parts of an aqueous s•olution containing 0. 05 part of xanthan gum and 0 .1 part of aluminum magnesium silicate is added thereto, and 10


5    parts of propylene glycol is further added, followed by stirring and mixing to prepare each flowable.

Formulation  Example  4

Three  parts  of  compound  I,   2  parts  of  the  compound  II -

i,    the  compound  II - ii,   the  compound  III,   the  compound  IV,

10    the compound V or the compound VI, 1 part of synt.hetic hydrous silicon oxide, 2 parts of calcium ligninsulfonate, 30 parts of bentonite and 62 parts of kaolin clay are

thoroughly ground and mixed. Water is added, and the mixture is thoroughly kneaded, granulated, and dried to

15 prepare each granule. Formulation Example 5



Eight parts of the compound I, 40 parts of the compound II - i, the compound II - ii, the compound III, the compound IV, the compound V or the compound VI, 3 parts of

20    calcium ligninsulfonate, 2 parts of sodium laurylsulfate,• and 45 parts of synthetic hydrous silicon oxide are thoroughly ground and mixed to• prepare each water

dispersible  powder.

Formulation  Example  6

25    Three  parts  of  the  compound  I,   2  parts  of  the  compound

•I

and an agrochemically acceptable salt of the compound represented by the formula (Ila) or

(lib).

3. A method for controlling a plant disease, which comprises applying a compound represented by the formula

(I):

as well as at least one compound A selected from the group consisting of a compound represented by the formula (II) and an agrochemically acceptable salt of the compound
t1    tl
•-~/Cli-c~Y
xt;l    {I!)

represented by the formula (II):    (Ct•ll)n-M~Q

wherein R~, Q, X, Y, Z, M and n are as defined in claim 1, to a plant, a seed of a plant or a cropland.

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