Title of Invention

ACID AMIDE DERIVATIVE AND FUNGICIDAL COMPOSITION COMPRISING IT

Abstract The invention discloses an acid amide derivative of formula (I) or a salt thereof, wherein R1, R2, R3, W1, W2, A and B are as defined in the specification. The invention is also for a fungicidal composition comprising said compound.
Full Text DESCRIPTION
TECHNICAL FIELD
The present invention relates to a fungicidal
composition containing an acid amide derivative.
BACKGROUND ART
WO2001/60783 and WO2003/27059 disclose that acid
amide derivatives having certain chemical structures are
useful as active ingredients for pesticides, but there is
no disclosure that compounds of the formula (I) given
hereinafter, have fungicidal activities. On the other
hand, Japanese Patent Application No. 2003-420864 by the
present applicants, discloses a fungicidal composition
containing an acid amide derivative as an active
ingredient, but the active ingredient compound of such a
composition is different from the compound of the formula
(I) given hereinafter.
Conventional many fungicidal compositions have had
practical problems such that either a preventive effect
or a curing effect is inadequate, the residual effect
tends to be inadequate, or the controlling effect against
plant diseases tends to be inadequate depending upon the
application site. Accordingly, a fungicidal composition
to overcome such problems has been desired.

DESCRIPTION
FUNGICIDAL. COMPOSITION CONTAINING ACID AMIDE DERIVATIVE
TECHNICAL FIELD
The present invention relates to a fungicidal
composition containing an acid amide derivative.
BACKGROUND ART
WO2001/60783 and WO2O03/27059 disclose that acid
amide derivatives having certain chemical structures are
useful as active ingredients for pesticides, but there is
no disclosure that compounds of the formula (I) given
hereinafter, have fungicidal activities. On the other
hand, Japanese Patent Application No. 2 003-4.20864 by the
present applicants, discloses a fungicidal composition
containing an acid amide derivative as an active
ingredient, but the active ingredient compound of such a
composition is different from the compound of the formula
(I) given hereinafter.


WO 00/73290 discloses isothiazole
carboxamides and their use as microbiocide. 3,7-
disubstituted benzthiazolones as known from EP-
0334134.
JACS, Vol.77, 1955, 1850-1852 discloses
benzamide compound which is an intermediate
compound of 2,5-diaryloxazoles.
A.P.Shkumat et al.: "2-(2-furyl)- and 2-(2-
thienyl)-5-aryloxazoles". UKRAINSKII KHIMICHESKII
ZHURNAL (RUSSIAN ED.), vol.53, no.5, 1987, pages
529-533, discloses furancarboxamides and
thiophenecarboxamides.
WO2004/005478 discloses ketone ligands for
modulating the expression of exogeneous genes via
an ecdysone receptor complex.
Conventional many fungicidal compositions have had
practical problems such that either a preventive effect
or a curing effect is inadequate, the residual effect
tends to be inadequate, or the controlling effect against
plant diseases tends to be inadequate depending upon the
application site. Accordingly, a fungicidal composition
to overcome such problems has been desired.

which may be substituted by Y, or naphthyl which may be
substituted by Y; X is halogen, alkyl which may be
substituted by E1, alkenyl which may be substituted by
E1, alkynyl which may be substituted by E1, hydroxy,
cyanooxy, alkoxy which may be substituted by E1,
alkenyloxy which may be substituted by E1, alkynyloxy
which may be substituted by E1, mercapto, cyanothio,
alkylthio which may be substituted by E1, alkenylthio
which may be substituted by E1, alkynylthio which may be
substituted by E , alkylsulfinyl which may be substituted
by E2, alkylsulfonyl which may be substituted by E2,
cycloalkyl which may be substituted by J, cycloalkyloxy
which may be substituted by J, cycloalkylthio which may
be substituted by J, cyano, nitro, formyl, phenyl which
may be substituted by Y, phenoxy which may be substituted
by Y, phenylthio which may be substituted by Y,
phenylalkyl which may be substituted by Y, phenylalkenyl
which may be substituted by Y, phenylalkynyl which may be
substituted by Y, phenylalkyloxy which may be substituted
by Y, phenylalkenyloxy which may be substituted by Y,
phenylalkynyloxy which may be substituted by Y,
phenylalkylthio which may be substituted by Y,
phenylalkenylthio which may be substituted by Y,
phenylalkynylthio which may be substituted by Y,
phenylamino which may be substituted by Y, -OR4, -SR5,
-NR6R7, -CO2R8, -C(=O)NR8R9, -S02NR8R9, -CH=NR10 , or
heterocyclic ring (the heterocyclic ring may be

substituted by halogen, alkyl, haloalkyl, alkoxy,
haloalkoxy, or alkylcarbonyl); Y is halogen, alkyl which
may be substituted by E1, alkenyl which may be
substituted by E1 , alkynyl which may be substituted by
E1 , hydroxy, cyanooxy, alkoxy which may be substituted by
E1 , alkenyloxy which may be substituted by E1 , alkynyloxy
which may be substituted by E1, mercapto, cyanothio,
alkylthio which may be substituted by E1, alkenylthio
which may be substituted by E1, alkynylthio which may be
substituted by E1, alkylsulfinyl which may be substituted
by E2, alkylsulfonyl which may be substituted by E2,
cycloalkyl which may be substituted by J, cycloalkyloxy
which may be substituted by J, cycloalkylthio which may
be substituted by J, cyano, nitro, formyl, -OR4, -SR5,
-NR6R7, -CO2R8, -C(=O)NR8R9, -S02NR8R9, -CH=NR10, or
heterocyclic ring (the heterocyclic ring may be
substituted by halogen, alkyl, haloalkyl, alkoxy,
haloalkoxy, pr alkylcarbonyl) ; each of R1 and R2 which
are independent of each other, is hydrogen, alkyl,
haloalkyl, hydroxyalkyl, alkoxyalkyl, haloalkoxyalkyl,
cyanoalkyl, alkoxycarbonylalkyl, alkenyl, haloalkenyl,
alkoxyalkenyl, alkynyl, haloalkynyl, alkoxyalkynyl,
cycloalkyl, halocycloalkyl, (alkyl)cycloalkyl,
(haloalkyl)cycloalkyl, cyano, or -CO2R8, or R1 and R2 may
together form a 3- to 6-membered saturated carbon ring;
R3 is hydrogen, alkyl which may be substituted by E1 ,
alkenyl which may be substituted by E1 , alkynyl which may

be substituted by E1 , hydroxy, cyanooxy, alkoxy which may
be substituted by E1, cycloalkyl which may be substituted
by J, cycloalkyloxy which may be substituted by J,
cycloalkylthio which may be substituted by J, cyano,
formyl, -C(=W3)R11-, -C(=W3)OR12, -C(=W3)SR12,
-C(=W3 )NR12R13 , -S(O)mR12, or -S (O) nNR12 R13 ; R4 is
-C(=W3)R12, -C(=W3)OR12, -C(=W3)SR12, -C (=W3 ) NR12 R13 ,
-S(O)mR12, -S (O)nNR12R13 , or heterocyclic ring (the
heterocyclic ring may be substituted by halogen, alkyl,
haloalkyl, alkoxy, haloalkoxy, or alkylcarbonyl); R5 is
-C(=W3)R12, -C(=W3)OR12, -C(=W3)SR12, -C (=W3 ) NR12 R13 , or
heterocyclic ring (the heterocyclic ring may be
substituted by halogen, alkyl, haloalkyl, alkoxy,
haloalkoxy, or alkylcarbonyl); R6 is hydrogen, alkyl,
haloalkyl, alkoxyalkyl, haloalkoxyalkyl, cyanoalkyl,
(cycloalkyl)alkyl, cycloalkyl, cyano, -C(=W3)R12,
-C (=W3 ) OR12 , -C(=W3)SR12, -C(=W3)NR12R13, -S(O)mR12,
-S(O)nNR12R13, or heterocyclic ring (the heterocyclic
ring may be substituted by halogen, alkyl, haloalkyl,
alkoxy, haloalkoxy, or an alkylcarbonyl); R7 is hydrogen,
alkyl, haloalkyl, alkoxyalkyl, or haloalkoxyalkyl; each
of R8 and R9 which are independent of each other, is
hydrogen, alkyl, haloalkyl, alkoxyalkyl, or
haloalkoxyalkyl, and adjacent R8 and R9 may together form
a ring; R10 is alkyl (the alkyl may be substituted by
halogen, alkoxy, or haloalkoxy), alkoxy (the alkoxy may
be substituted by halogen, alkoxy, or haloalkoxy),

alkenyloxy (the alkenyloxy may be substituted by halogen,
alkoxy, or haloalkoxy), alkynyloxy (the alkynyloxy may be
substituted by halogen, alkoxy, or haloalkoxy)., or
alkoxycarbonyl (the alkoxycarbonyl may be substituted by
halogen, alkoxy, or haloalkoxy); R11 is hydrogen, alkyl
which may be substituted by E3, phenyl (the phenyl may be
substituted by halogen, alkyl, haloalkyl, alkoxy,
haloalkoxy, or alkylcarbonyl), or heterocyclic ring (the
heterocyclic ring may be substituted by halogen, alkyl,
haloalkyl, alkoxy, haloalkoxy, or alkylcarbonyl); each of
R12 and R1 which are independent of each other, is alkyl
which may be substituted by E3, alkoxy, haloalkoxy,
cycloalkyl which may be substituted by J, or phenyl (the
phenyl may be substituted by halogen, alkyl, haloalkyl,
alkoxy, haloalkoxy, or alkylcarbonyl), or adjacent R12
and R13 may together form a ring; each of W1, W2 and W3
which are independent of one another, is oxygen or
sulfur; each of m and n which are independent of each
other, is an integer of from 0 to 2; E1 is halogen,
hydroxy, alkoxy, haloalkoxy, mercapto, alkylthio,
haloalkylthio, alkylsulfonyl, cycloalkyl, amino,
monoalkylamino, dialkylamino, cyano, nitro,
hydroxycarbonyl, alkoxycarbonyl, alkylcarbonyloxy,
trialkylsilyl, or heterocyclic ring (the heterocyclic
ring may be substituted by halogen, alkyl, haloalkyl,
alkoxy, haloalkoxy, or alkylcarbonyl); E2 is halogen,
hydroxy, alkoxy, haloalkoxy, cycloalkyl, amino,

monoalkylamino, dialkylamino, cyano, nitro,
hydroxycarbonyl, alkoxycarbonyl, trialkylsilyl, or
heterocyclic ring (the heterocyclic ring may be
substituted by halogen, alkyl, haloalkyl, alkoxy,
haloalkoxy, or alkylcarbonyl); E3 is halogen, alkoxy,
alkylthio, amino, monoalkylamino, dialkylamino,
cycloalkyl, cyano, alkoxycarbonyl, haloalkoxy,
haloalkylthio, or phenyl (the phenyl may be substituted
by halogen, alkyl, haloalkyl, alkoxy, haloalkoxy, or
alkylcarbonyl); and J is halogen, alkyl, haloalkyl,
alkoxy, or haloalkoxy. Further, the present invention
provides a method for controlling various noxious fungi,
or various diseases caused by various noxious fungi,
which comprises applying an effective amount of such an
acid amide derivative or a salt thereof, or a method for
protecting crop plants or improving crop yields, which
comprises applying an effective amount of such an acid
amide derivative or a salt thereof. Further, the present
invention provides an acid amide derivative of the
formula (I-α) or a salt thereof, which has not been known
specifically heretofore:

wherein Aα is phenyl which may be substituted by Xα,
naphthyl substituted by Xα, thienyl substituted by Xα,

benzodioxolanyl which, may be substituted Xα, or
benzodioxanyl which may be substituted Xα; B is
heterocyclic ring (excluding pyridyl) which may be
substituted by Y, fused heterocyclic ring which may be
substituted by Y, or naphthyl which may be substituted by
Y; Xα is fluorine, chlorine, iodine, alkyl, haloalkyl,
alkoxyalkyl, dialkylaminoalkyl, alkynyl,
trialkylsilylalkynyl, hydroxy, alkoxy, haloalkoxy,
alkoxyalkoxy, cycloalkyl, nitro, phenyl, phenylalkynyl,
pyridyloxy which may be substituted by haloalkyl,
alkylcarbonyloxy, alkylsulfonyloxy, or heterocyclic ring
(the heterocyclic ring may be substituted by halogen,
alkyl, or alkylcarbonyl) ,- Y is halogen, alkyl which may
be substituted by E1 , alkenyl which may be substituted by
E1 , alkynyl which may be substituted by E1, hydroxy,
cyanooxy, alkoxy which may be substituted by E1,
alkenyloxy which may be substituted by E1 , alkynyloxy
which may be substituted by E1 , mercapto, cyanothio,
alkylthio which may be substituted by E1 , alkenylthio
which may be substituted by E1, alkynylthio which may be
substituted by E1, alkylsulfinyl which may be substituted
by E2, alkylsulfonyl which may be substituted by E2,
cycloalkyl which may be substituted by J, cycloalkyloxy
which may be substituted by J, cycloalkylthio which may
be substituted by J, cyano, nitro, formyl, -OR4, -SR5,
-NR6R7, -CO2R8, -C(=O)NR8R9, -SO2NR8R9, -CH=NR10, or
heterocyclic ring (the heterocyclic ring may be

substituted by halogen, alkyl, haloalkyl, alkoxy,
haloalkoxy, or alkylcarbonyl); each of R1 and R2 which
are independent of each other, is hydrogen, alkyl,
haloalkyl, hydroxyalkyl, alkoxyalkyl, haloalkoxyalkyl,
cyanoalkyl, alkoxycarbonylalkyl, alkenyl, haloalkenyl,
alkoxyalkenyl, alkynyl, haloalkynyl, alkoxyalkynyl,
cycloalkyl, halocycloalkyl, (alkyl)cycloalkyl,
(haloalkyl)cycloalkyl, cyano, or -CO2R8, or R1 and R2 may
together form a 3- to 6-membered saturated carbon ring;
R3 is hydrogen, alkyl which may be substituted by E1 ,
alkenyl which may be substituted by E1, alkynyl which may
be substituted by E1, hydroxy, cyanooxy, alkoxy which may
be substituted by E1, cycloalkyl which may be substituted
by J, cycloalkyloxy which may be substituted by J,
cycloalkylthio which may be substituted by J, cyano,
formyl, -C(=W3)R11, -C(=W3)OR12, -C(=W3)SR12,
-C(=W3 )NR12R13 , -S(O)mR12, or S(O)nNR12R13 ; R4 is
-C(=W3)R12, -C(=W3)OR12, -C(=W3)SR12, -C (=W3 ) NR12 R13 ,
-S(O)mR12, -S(O)nNR12R13 , or heterocyclic ring (the
heterocyclic ring may be substituted by halogen, alkyl,
haloalkyl, alkoxy, haloalkoxy, or alkylcarbonyl); R5 is
-C(=W3)R12, -C(=W3)OR12, -C(=W3 )SR12 , -C(=W3)NR12R13, or
heterocyclic ring (the heterocyclic ring may be
substituted by halogen, alkyl, haloalkyl, alkoxy,
haloalkoxy, or alkylcarbonyl); R6 is hydrogen, alkyl,
haloalkyl, alkoxyalkyl, haloalkoxyalkyl, cyanoalkyl,
(cycloalkyl)alkyl, cycloalkyl, cyano, -C(=W3)R12 ,

-C(=W3)OR12, -C(=W3)SR12, -C(=W3 )NR12R13 , -S(O)mR12,
-S(O)nNR12 R13, or heterocyclic ring (the heterocyclic
ring may be substituted by halogen, alkyl, -haloalkyl,
alkoxy, haloalkoxy, or alkylcarbonyl); R7 is hydrogen,
alkyl, haloalkyl, alkoxyalkyl, or haloalkoxyalkyl; each
of R8 and R9 which are independent of each other, is
hydrogen, alkyl, haloalkyl, alkoxyalkyl, or
haloalkoxyalkyl, and adjacent R8 and R9 may together form
a ring; R10 is alkyl (the alkyl may be substituted by
halogen, alkoxy, or haloalkoxy), alkoxy (the alkoxy may
be substituted by halogen, alkoxy, or haloalkoxy),
alkenyloxy (the alkenyloxy may be substituted by halogen,
alkoxy, or haloalkoxy), alkynyloxy (the alkynyloxy may be
substituted by halogen, alkoxy, or haloalkoxy), or
alkoxycarbonyl (the alkoxycarbonyl may be substituted by
halogen, alkoxy, or haloalkoxy); R11 is hydrogen, alkyl
which may be substituted by E3, phenyl (the phenyl may be
substituted by halogen, alkyl, haloalkyl, alkoxy,
haloalkoxy, or alkylcarbonyl), or heterocyclic ring (the
heterocyclic ring may be substituted by halogen, alkyl,
haloalkyl, alkoxy, haloalkoxy, or alkylcarbonyl); each of
R12 and R13 which are independent of each other, is alkyl
which may be substituted by E3, alkoxy, haloalkoxy,
cycloalkyl which may be substituted by J, or phenyl (the
phenyl may be substituted by halogen, alkyl, haloalkyl,
alkoxy, haloalkoxy, or alkylcarbonyl), and adjacent R12
and R13 may together form a ring; each of W1 , W2 and W3

which are independent of one another, is oxygen or
sulfur; each of m and n which are independent of each
other, is an integer of from 0 to 2; E1 is halogen,
hydroxy, alkoxy, haloalkoxy, mercapto, alkylthio,
haloalkylthio, alkylsulfonyl, cycloalkyl, amino,
monoalkylamino, dialkylamino, cyano, nitro,
hydroxycarbonyl, alkoxycarbonyl, alkylcarbonyloxy,
trialkylsilyl, or heterocyclic ring (the heterocyclic
ring may be substituted by halogen, alkyl, haloalkyl,
alkoxy, haloalkoxy, or alkylcarbonyl) ,- E2 is halogen,
hydroxy, alkoxy, haloalkoxy, cycloalkyl, amino,
monoalkylamino, dialkylamino, cyano, nitro,
hydroxycarbonyl, alkoxycarbonyl, trialkylsilyl, or
heterocyclic ring (the heterocyclic ring may be
substituted by halogen, alkyl, haloalkyl, alkoxy,
haloalkoxy, or alkylcarbonyl) ; E3 is halogen, alkoxy,
alkylthio, amino, monoalkylamino, dialkylamino,
cycloalkyl, cyano, alkoxycarbonyl, haloalkoxy,
haloalkylthio, or phenyl (the phenyl may be substituted
by halogen, alkyl, haloalkyl, alkoxy, haloalkoxy, or
alkylcarbonyl); and J is halogen, alkyl, haloalkyl,
alkoxy, or haloalkoxy.
In the above formula (I), the number of substituents
X contained in A may be one or more, and in the case of
more than one, such substituents may be the same or
different. The number of halogen, alkyl or alkoxy which
is substituent(s) on indanyl or tetrahydronaphthyl

contained in A, may be one or more, and in the case of
more than one, such substituents may be the same or
different. The-number of substituents Y contained in B
or X may be one or more, and in the case of more than
one, such substituents may be the same or different. The
number of substituents E1, E2 or E3 contained in X, Y,
R3, R11, R12 or R13, may be one or more, and in the case
of more than one, such substituents may be the same or
different. The number of substituents J contained in X,
Y, R3, R12 or R13, may be one or more, and in the case of
more than one, such substituents may be the same or
different. The number of halogen, alkyl, haloalkyl,
alkoxy, haloalkoxy, or alkylcarbonyl, which is
substituent(s) on phenyl or heterocyclic ring contained
in X, Y, R4 , R5 , R6 , R11 , R12 , R13, E1 , E2 or E3 , maybe
one or more, and in the case of more than one, such
substituents may be the same or different. The number of
halogen, alkoxy or haloalkoxy, which is substituent(s) on
alkyl, alkoxy, alkenyloxy, alkynyloxy or alkoxycarbonyl,
contained in R10, may be one or more, and in the case of
more than one, such substituents may be the same or
different.
The heterocyclic ring in A, B, X, Y, R4, R5, R6, R11 ,
E1 or E2, is preferably a 3-, 5- or 6-membered
heterocyclic ring containing from 1 to 4 atoms of at
least one type selected from the group consisting of 0, S
and N, and it may, for example, be a 3-membered

heterocyclic ring such as oxiranyl; a 5-membered
heterocyclic ring such as furyl, tetrahydrofuryl,
thienyl, pyrrolyl, pyrrolinyl, pyrrolidinyl, dioxolanyl,
oxazolyl, isoxazolyl, thiazolyl, isothiazolyl,
imidazolyl, imidazolinyl, imidazolidinyl, pyrazolyl,
pyrazolinyl, pyrazolidinyl, triazolyl, oxadiazolyl,
thiadiazolyl or tetrazolyl; a 6-membered heterocyclic
ring such as pyranyl, pyridyl, piperidinyl, dioxanyl,
oxazinyl, morpholinyl, thiazinyl, pyridazinyl,
pyrimidinyl, pyrazinyl, piperazinyl or triazinyl.
The fused heterocyclic ring in A or B is preferably
a 8- to 10-membered fused heterocyclic ring containing
from 1 to 4 atoms of at least one type selected from the
group consisting of 0, S and N, and it may, for example,
be benzofuranyl, isobenzofuranyl, dihydrobenzofuranyl,
dihydroisobenzofuranyl, benzothienyl, isobenzothienyl,
dihydrobenzothienyl, dihydroisobenzothienyl,.
tetrahydrobenzothienyl, indolyl, isoindolyl,
benzoxazolyl, benzothiazolyl, indazolyl, benzimidazolyl,
benzodioxolanyl, benzodioxanyl, chromenyl, chromanyl,
isochromanyl, chromonyl, chromanonyl, quinolyl,
isoquinolyl, cinnolinyl, phthalazinyl, cjuinazolinyl,
quinoxalinyl, indolizinyl, quinolizinyl, imidazopyridyl,
naphthyridinyl, pteridinyl, dihydrobenzoxazinyl,
dihydrobenzoxazolinonyl, dihydrobenzoxazinonyl or
benzothioxanyl.
The alkyl or alkyl moiety in A, X, Y, R1 to R3, R6 to

R13, E1 to E3 or J, may be linear or branched, and as a
specific example thereof, C1-7 alkyl may be mentioned such
as-methyl, ethyl, propyl, isopropyl, butyl, tert-butyl,
pentyl, hexyl or heptyl.
The cycloalkyl or cycloalkyl moiety in X, Y, R1 to
R3 , R6 , R12, R13 or E1 to E3, may be one having from 3 to
6 carbon atoms, such as cyclopropyl, cyclopentyl or
cyclohexyl. Further, a specific example of the 3- to 6-
membered saturated carbon ring which R1 and R2 may
together form, may be cyclopropyl, cyclobutyl,
cyclopentyl or cyclohexyl.
The alkenyl or alkenyl moiety in X, Y, R1 to R3 or
R10, may be a linear or branched one having from 2 to 7
carbon atoms, such as vinyl, 1-propenyl, allyl,
isopropenyl, 1-butenyl, 1,3-butadienyl, 1-hexenyl or 1-
heptenyl. Further, the alkynyl or alkynyl moiety in X,
Y, R1 to R3 or R1°, may be a linear or branched one
having from 2 to 7 carbon atoms, such as ethynyl, 2-
butynyl, 2-pentynyl, 3-hexynyl or 4-dimethyl-2-pentynyl.
The halogen or the halogen as a substituent in A, X,
Y, R1 to R13, E1 to E3 or J may be an atom of fluorine,
chlorine, bromine or iodine. The number of halogen as
substituent(s), may be one or more, and in the case of
more than one, such halogens may be the same or
different. Further, such halogens may be substituted at
any positions.
The definition of substituent Aα or Xα in the above

formula (I-a) follows the definition of substituent A or
X in the above formula (I), respectively.
The salt of the acid amide derivative of the above
formula (I) or (I-α) may be any salt so long as it is
agriculturally acceptable. For example, it may be an
alkali metal salt such as a sodium salt or a potassium
salt; an alkaline earth metal salt such as a magnesium
salt or a calcium salt; an inorganic acid salt such as a
hydrochloride, a perchlorate, a sulfate or a nitrate; or
an organic acid salt such as an acetate or a methane
sulfonate.
The acid amide derivative of the above formula (I)
or (I-a) has various isomers such as optical isomers or
geometrical isomers, and the present invention includes
both isomers and mixtures of such isomers. Further, the
present invention also includes various isomers other
than the above isomers within the common knowledge in the
technical field concerned. Further, depending upon the
types of isomers, they may have chemical structures
different from the above formula (I) or (I-α), but they
are within the scope of the present invention, since it
is obvious to those skilled in the art that they are
isomers.
The acid amide derivative of the above formula (I)
or (I-a) or a salt thereof can be produced by the
following reactions (A) to (K), (U) to (W), or by a usual
process for producing a salt.


In the reaction (A) , A, B, R1, and R2, are as defined
above. Z is hydroxy, alkoxy or halogen, and the halogen
may be an atom of fluorine, chlorine, bromine or iodine.
Reaction (A) may be carried out usually in the
presence of a base and a solvent.
The base may be one or more suitably selected from
e.g. an alkali metal such as sodium or potassium; an
alkali metal alkoxide such as sodium methoxide, sodium
ethoxide or potassium tertiary butoxide; a carbonate such
as sodium carbonate or potassium carbonate; a bicarbonate
such as sodium bicarbonate or potassium bicarbonate; a
metal hydroxide such as sodium hydroxide or potassium
hydroxide; a metal hydride such as sodium hydride or
potassium hydride; an amine such as monomethylamine,
dimethylamine or triethylamine; a pyridine such as
pyridine or 4-dimethylaminopyridine; and an organic
lithium such as methyllithium, n-butyllithium or lithium
diisopropyl amide. The base may be used in an amount of
from 1 to 3 mols, preferably from 1 to 2 mols, per mol of
the compound of the formula (II).
The solvent may be any solvent so long as it is a
solvent inert to the reaction. For example, it may be

one or more suitably selected from e.g. an aromatic
hydrocarbon such as benzene, toluene, xylene or
chlorobenzene; an aliphatic hydrocarbon such as carbon
tetrachloride, methyl chloride, chloroform,
dichloromethane, dichloroethane, trichloroethane, hexane
or cyclohexane; an ether such as dioxane, tetrahydrofuran,
diethyl ether or dimethoxyethane; an ester such as methyl
acetate or ethyl acetate; a polar aprotic solvent such as
dimethyl sulfoxide, sulfolane, dimethylacetamide,
dimethylformamide, N-methylpyrrolidone, pyridine
acetonitrile or propionitrile; and a ketone such as
acetone or methyl ethyl ketone.
Reaction (A) may be carried out, if necessary, in the
presence of a dehydration condensation agent. The
dehydration condensation agent may, for example, be N,N'-
dicyclohexylcarbodiimide, chlorosulfonyl isocyanate,
N,N'-carbonyldiimidazole and trifluoroacetic anhydride.
The reaction temperature for reaction (A) is usually
from 0 to 10 0°C, preferably from 0 to 50°C, and the
reaction time is usually from 0.5 to 48 hours, preferably
from 1 to 24 hours.

In reaction (B), A, B, R1 and R2 are as defined
above, and R3a is alkyl which may be substituted by E1,

alkenyl which may be substituted by E1 , alkynyl which may
be substituted by E1, hydroxy, cyanooxy, alkoxy which may
be substituted by E1, cycloalkyl which may be substituted
by J, cycloalkyloxy which may be substituted by J,
cycloalkylthio which may be substituted by J, cyano,
formyl, -C(=W3)R11, -C (=W3 ) OR12 , -C(=W3)SR12,
-C(=W3 )NR12R13 , -S(O)mR12 or S (O) riNR12 R13 (E1 , J, R11 ,
R12, R13, W3, m and n are as defined above) and T is
halogen, and the halogen may be an atom of fluorine,
chlorine, bromine or iodine.
Reaction (B) may be carried out usually in the
presence of a base and a solvent.
The base may be one or more suitably selected from
e.g. an alkali metal such as sodium or potassium; an
alkali metal alkoxide such as sodium methoxide, sodium
ethoxide or potassium tertiary butoxide; a carbonate such
as sodium carbonate or potassium carbonate; a bicarbonate
such as sodium bicarbonate or potassium bicarbonate; a
metal hydroxide such as sodium hydroxide or potassium
hydroxide; a metal hydride such as sodium hydride or
potassium hydride; an amine such as monomethylamine,
dimethylamine or triethylamine; and a pyridine such as
pyridine or 4-dimethylaminopyridine. The base may be
used in an amount of from 1 to 3 mols, preferably from 1
to 1.5 mols, per mol of the compound of the formula (1-1) .
The solvent may be any solvent so long as it is a
solvent inert to the reaction. For example, it may be

one or more suitably selected from e.g. an aromatic
hydrocarbon such as benzene, toluene, xylene or
chlorobenzene; an aliphatic hydrocarbon such as carbon
tetrachloride, methyl chloride, chloroform,
dichloromethane, dichloroethane, trichloroethane, hexane
or cyclohexane; an ether such as dioxane, tetrahydrofuran,
diethyl ether or dimethoxyethane; an ester such as methyl
acetate or ethyl acetate; a polar aprotic solvent such as
dimethyl sulfoxide, sulfolane, dimethylacetamide,
dimethylformamide, N-methylpyrrolidone or pyridine; a
nitrile such as acetonitrile, propionitrile or
acrylonitrile; and a ketone such as acetone or methyl
ethyl ketone.
The reaction temperature for reaction (B) is usually
from 0 to 100°C, preferably from 0 to 50°C, and the
reaction time is usually from 1 to 300 hours, preferably
from 1 to 150 hours.

In reaction (C), A, R1 and R2 are as defined above,
and B1 is a heterocyclic ring substituted by -CO2H, or a
fused heterocyclic ring substituted by -CO2H. The
formula (V) is anhydrous dicarboxylic acid of Q (phenyl,

a heterocycle or a fused heterocycle).
Reaction (C) may be carried out usually in the
presence of a solvent. The solvent may be any solvent so
long as it is a solvent inert to the reaction. For
example, it may be one or more suitably selected from e.g.
an aromatic hydrocarbon such as benzene, toluene, xylene
or chlorobenzene; an aliphatic hydrocarbon such as carbon
tetrachloride, methyl chloride, chloroform,
dichloromethane, dichloroethane, trichloroethane, hexane
or cyclohexane; an ether such as dioxane, tetrahydrofuran,
diethyl ether or dimethoxyethane; an ester such as methyl
acetate or ethyl acetate; a polar aprotic solvent such as
dimethyl sulfoxide, sulfolane, dimethylacetamide,
dimethylformamide, N-methylpyrrolidone or pyridine; a
nitrile such as acetonitrile, propionitrile or
acrylonitrile; a ketone such as acetone or methyl ethyl
ketone; and an alcohol such as methanol, ethanol,
propanol or tert-butanol.
Reaction (C) may be carried out, if necessary, in
the presence of a base. The base may be one or more
suitably selected from e.g. an alkali metal such as
sodium or potassium; an alkali metal alkoxide such as
sodium methoxide, sodium ethoxide or potassium tertiary
butoxide; a carbonate such as sodium carbonate or
potassium carbonate; a bicarbonate such as sodium
bicarbonate or potassium bicarbonate; a metal hydroxide
such as sodium hydroxide or potassium hydroxide; a metal

hydride such as sodium hydride or potassium hydride; an
amine such as monomethylamine, dimethylamine or
triethylamine; and a pyridine such as pyridine or 4-
dimethylaminopyridine. The base may be used in an amount
of from 1 to 3 mols, preferably from 1 to 1.5 mols, per
mol of the compound of the formula (II).
The reaction temperature for reaction (C) is
usually from 0 to 150°C, preferably from 0 to 80°C. The
reaction time is usually from 0.5 to 9 6 hours, preferably
from 1 to 48 hours.

In reaction (D), A, R1 and R2 are as defined above.
B2 is a heterocyclic ring substituted by Y2, or a fused
heterocyclic ring substituted by Y2, B3 is a heterocyclic
ring substituted by Y3, or a fused heterocyclic ring
substituted by Y3, Y2 is an atom of chlorine, bromine or
iodine, and Y3 is an unsaturated heterocyclic ring (the
unsaturated heterocyclic ring may be substituted by
halogen, alkyl, haloalkyl, alkoxy or haloalkoxy).
Reaction (D) may be carried out usually in the
presence of a catalyst, a base, a solvent and an inert
gas .
The catalyst may be one or more suitably selected
from e.g. palladium complexes such as tetrakis

{triphenylphosphine)palladium(O), bis
(dibenzylideneacetone)palladium(O), and tris
(dibenzylideneacetone)dipalladium(O).
The base may be one or more suitably selected from
e.g. a carbonate such as sodium carbonate, potassium
carbonate or calcium carbonate; a bicarbonate such as
sodium bicarbonate or potassium bicarbonate; and a metal
hydroxide such as sodium hydroxide or potassium hydroxide.
The base may be used in an amount of from 1 to 20 mols,
preferably from 1 to 10 mols, per mol of the compound of
the formula (I-4).
The solvent may be any solvent so long as it is a
solvent inert to the reaction. For example, it may be
one or more suitably selected from e.g. an aromatic
hydrocarbon such as benzene, toluene, xylene or
chlorobenzene; an aliphatic hydrocarbon such as carbon
tetrachloride, methyl chloride, chloroform,
dichloromethane, dichloroethane, trichloroethane, hexane
or cyclohexane; an ether such as dioxane, tetrahydrofuran,
diethyl ether or dimethoxyethane; an ester such as methyl
acetate or ethyl acetate; a polar aprotic solvent such as
dimethyl sulfoxide, sulfolane, dimethylacetamide,
dimethylformamide, N-methylpyrrolidone or pyridine; a
nitrile such as acetonitrile, propionitrile or
acrylonitrile; a ketone such as acetone or methyl ethyl
ketone; an alcohol such as methanol, ethanol, propanol or
tert-butanol; and water.

The inert gas may, for example, be nitrogen gas or
argon gas.
The reaction temperature for reaction (D) is usually
from 0 to 150°C, preferably from 15 to 100°C. The
reaction time is usually from 0.5 to 96 hours, preferably
from 1 to 48 hours.

In reaction (E) , A, R1 and R2 are as defined above,
and B4 is a heterocyclic ring substituted by -CO2H, or a
fused heterocyclic ring substituted by -CO2H, B5 is a
heterocyclic ring substituted by -CO2 R8a, or a fused
heterocyclic ring substituted by -CO2 R8a, and R8a is
alkyl, haloalkyl, alkoxyalkyl or haloalkoxyalkyl.
The first step in reaction (E) may be carried out in
the presence of a chlorination agent. The chlorination
agent may be one or more suitably selected from e.g.
thionyl chloride, oxalyl chloride and phosphorus
pentachloride.
The first step in reaction (E) may be carried out, if
necessary, in the presence of a solvent. The solvent may
be any solvent so long as it is a solvent inert to the
reaction. For example, it may be one or more suitably
selected from e.g. an aromatic hydrocarbon such as

benzene, toluene, xylene or chlorobenzene; an aliphatic
hydrocarbon such as carbon tetrachloride, methyl chloride,
chloroform, dichloromethane, dichloroethane,
trichloroethane, hexane or cyclohexane; an ether such as
dioxane, tetrahydrofuran, diethyl ether or
dimethoxyethane; and an ester such as methyl acetate or
ethyl acetate.
The reaction temperature for the first step in
reaction (E) is usually from 0 to 200°C, preferably from
15 to 150°C. The reaction time is usually from 0.1 to 72
hours, preferably from 0.5 to 3 hours.
The second step in reaction (E) may be carried out,
if necessary, in the presence of a base. The base may be
one or more suitably selected from e.g. an alkali metal
such as sodium or potassium; an alkali metal alkoxide
such as sodium methoxide, sodium ethoxide or potassium
tertiary butoxide; a carbonate such as sodium carbonate
or potassium carbonate; a bicarbonate such as sodium
bicarbonate or potassium bicarbonate; a metal hydroxide
such as sodium hydroxide or potassium hydroxide; a metal
hydride such as sodium hydride or potassium hydride; an
amine such as monomethylamine, dimethylamine or
triethylamine; and a pyridine such as pyridine or 4-
dimethylaminopyridine. The base may be used in an amount
of from 1 to 5 mols, preferably from 1 to 2 mols, per mol
of the compound of the formula (1-6) .
The second step in reaction (E) may be carried out,

defined above.
Reaction (F) may be carried out usually in the
presence of a catalyst or a dehydration condensation
agent.
The catalyst may be one or more suitably selected
from e.g. a mineral acid such as hydrochloric acid or
sulfuric acid; an organic acid such as paratoluene
sulfonic acid; and a Lewis acid such as boron trifluoride
etherate.
The dehydration condensation agent may be one or more
suitably selected from e.g. N,N'-dicyclohexylcarbodiimide,
chlorosulfonyl isocyanate, N,N'-carbonyldiimidazole and
trifluoroacetic anhydride.
Reaction (F) may be carried out, if necessary, in the
presence of a solvent. The solvent may be any solvent so
long as it is a solvent inert to the reaction. For
example, it may be one or more suitably selected from e.g.
an aromatic hydrocarbon such as benzene, toluene, xylene
or chlorobenzene; an aliphatic hydrocarbon such as carbon
tetrachloride, methyl chloride, chloroform,
dichloromethane, dichloroethane, trichloroethane, hexane
or cyclohexane; an ether such as dioxane, tetrahydrofuran,
diethyl ether or dimethoxyethane; an ester such as methyl
acetate or ethyl acetate; a polar aprotic solvent such as
dimethyl sulfoxide, sulfolane, dimethylacetamide,
dime thy lformamide, N-methylpyrrolidone or pyridine; a
nitrile such as acetonitrile, propionitrile or

acrylonitrile; a ketone such as acetone or methyl ethyl
ketone; and an alcohol such as methanol, ethanol,
propanol or tert-butanol. Further, in this reaction, the
compound of the formula (VII) may serve also as a solvent
if used excessively.
The reaction temperature for reaction (F) is usually
from 0 to 200°C, preferably from 0 to 100°C. The reaction
time is usually from 0.1 to 96 hours, preferably from 0.5
to 24 hours.

In reaction (G), A, B4, R1, R2, R8 and R9 are as
defined above, and B6 is a heterocyclic ring substituted
by -CONR8R9, or a fused heterocyclic ring substituted by
-CONR8R9 (wherein R8 and R9 are as defined above).
The first step in reaction (G) may be carried out in
accordance with the first step in the above-described
reaction (E).
The second step in the reaction (G) may be carried
out, if necessary, in the presence of a base. The base
may be one or more suitably selected from e.g. an alkali
metal such as sodium or potassium; an alkali metal
alkoxide such as sodium methoxide, sodium ethoxide or
potassium tertiary butoxide; a carbonate such as sodium

carbonate or potassium carbonate; a bicarbonate such as
sodium bicarbonate or potassium bicarbonate; a metal
hydroxide such as sodium hydroxide or potassium
hydroxide; a metal hydride such as sodium hydride or
potassium hydride; an amine such as monomethylamine,
dimethylamine or triethylamine; and a pyridine such as
pyridine or 4-dimethylaminopyridine. The base may be
used in an amount of from 1 to 10 mols, preferably from 1
to 2 mols, per mol of the compound of the formula (1-6).
The second step in reaction (G) may be carried out,
if necessary, in- the presence of a solvent. The solvent
may be any solvent so long as it is a solvent inert to
the reaction. For example, it may be one or more
suitably selected from e.g. an aromatic hydrocarbon such
as benzene, toluene, xylene or chlorobenzene; an
aliphatic hydrocarbon such as carbon tetrachloride,
methyl chloride, chloroform, dichloromethane,
dichloroethane, trichloroethane, hexane or cyclohexane;
an ether such as dioxane, tetrahydrofuran, diethyl ether
or dimethoxyethane,- an ester such as methyl acetate or
ethyl acetate; a polar aprotic solvent such as dimethyl
sulfoxide, sulfolane, dimethylacetamide,
dimethylformamide, N-methylpyrrolidone or pyridine; a
nitrile such as acetonitrile, propionitrile or
acrylonitrile; a ketone such as acetone or methyl ethyl
ketone; and water.
The reaction temperature for the second step in

reaction (G) is usually from 0 to 100°C, preferably from
0 to 5 0°C. The reaction time is usually from 0.1 to 48
hours, preferably from 0.5 to 6 hours.

In reaction (H), A, B4, B6, R1, R2 , R8 and R9 are as
defined above.
Reaction (H) may be carried out usually in the
presence of a dehydration condensation agent and a
solvent.
The dehydration condensation agent may be one or more
suitably selected from e.g. N,N'-dicyclohexylcarbodiimide,
chlorosulfonyl isocyanate, N,N'-carbonyldiimidazole and
trifluoroacetic anhydride.
The solvent may be any solvent so long as it is a
solvent inert to the reaction. For example, it may be
one or more suitably selected from e.g. an aromatic
hydrocarbon such as benzene, toluene, xylene or
chlorobenzene; an aliphatic hydrocarbon such as carbon
tetrachloride, methyl chloride, chloroform,
dichloromethane, dichloroethane, trichloroethane, hexane
or cyclohexane; an ether such as dioxane, tetrahydrofuran,
diethyl ether or dimethoxyethane; an ester such as methyl
acetate or ethyl acetate; a polar aprotic solvent such as
dimethyl sulfoxide, sulfolane, dimethylacetamide,

dimethylformamide, N-methylpyrrolidcne or pyridine; a
nitrile such as acetonitrile, propionitrile or
acrylonitrile; and a ketone such as acetone or methyl
ethyl ketone.
The reaction temperature for the reaction (H) is
usually from 0 to 200°C, preferably from 0 to 100°C. The
reaction time is usually from 0.1 to 9 6 hours, preferably
from 0.5 to 24 hours.

In reaction (I), A, B5, B6, R1, R2 , R8 and R9 are as
defined above.
Reaction (I) may be carried out usually in the
presence of a solvent. The solvent may be any solvent so
long as it is a solvent inert to the reaction. For
example, it may be one or more suitably selected from e.g.
an aromatic hydrocarbon such as benzene, toluene, xylene
or chlorobenzene; an aliphatic hydrocarbon such as carbon
tetrachloride, methyl chloride, chloroform,
dichloromethane, dichloroethane, trichloroethane, hexane
or cyclohexane; an ether such as dioxane, tetrahydrofuran,
diethyl ether or dimethoxyethane; an ester such as methyl
acetate or ethyl acetate; a polar aprotic solvent such as
dimethyl sulfoxide, sulfolane, dimethylacetamide,
dimethylformamide, N-methylpyrrolidone or pyridine; a

nitrile such as acetonitrile, propionitrile or
acrylonitrile; a ketone such as acetone or methyl ethyl
ketone; an alcohol such as methanol, ethanol, propanol or
tert-butanol; and water. Further, in this reaction, the
compound of the formula (VIII) may serve also as a
solvent if used excessively.
The reaction temperature for the reaction (I) is
usually from 0 to 150°C, preferably from 0 to 80°C. The
reaction time is usually from 0.1 to 48 hours, preferably
from 0.5 to 24 hours.

In reaction (J), B is as defined above, A1 is phenyl
substituted by -OR4, benzyl substituted by -OR4, naphthyl
substituted by -OR4, a heterocyclic ring substituted by
-OR4 or a fused heterocyclic ring substituted by -OR4
(wherein R4 is defined above), A2 is phenyl substituted
by -OH, benzyl substituted by -OH, naphthyl substituted
by -OH, a heterocyclic ring substituted by -OH or a fused
heterocyclic ring substituted by -OH, each of Rla and R2a
is alkyl, haloalkyl, hydroxyalkyl, alkoxyalkyl,
haloalkoxyalkyl, cyanoalkyl, alkoxycarbonylalkyl, alkenyl,
haloalkenyl, alkoxyalkenyl, alkynyl, haloalkynyl,
alkoxyalkynyl, cycloalkyl, halocycloalkyl,
(alkyl)cycloalkyl, (haloalkyl)cycloalkyl or cyano, and

R1a and R2a may together form a 3- to 6-membered saturated
carbocycle, and M is sodium or potassium.
Reaction (J) may be usually carried out in the
presence of a solvent. The solvent may be any solvent so
long as it is a solvent inert to the reaction. For
example, it may be one or more suitably selected from e.g.
an aromatic hydrocarbon such as benzene, toluene, xylene
or chlorobenzene; an aliphatic hydrocarbon such as carbon
tetrachloride, methyl chloride, chloroform,
dichloromethane, dichloroethane, trichloroethane, hexane
or cyclohexane; an ether such as dioxane, tetrahydrofuran,
diethyl ether or dimethoxyethane; a polar aprotic solvent
such as dimethyl sulfoxide, sulfolane, dimethylacetamide,
dimethylformamide, N-methylpyrrolidone or pyridine; a
nitrile such as acetonitrile, propionitrile or
acrylonitrile; a ketone such as acetone or methyl ethyl
ketone; an alcohol such as methanol, ethanol, propanol or
tert-butanol; and water.
The reaction temperature for reaction (J) is usually
from 0 to 100°C, preferably from 20 to 80°C. The reaction
time is usually from 0.1 to 24 hours, preferably from 0.1
to 12 hours.


In reaction (K) , A1, A2, B, R1a , R2a and R4 are as
defined above, G is an atom of chlorine, bromine or
iodine. ...
Reaction (K) may be usually carried out in the
presence of a base and a solvent.
The base may be one or more suitably selected from
e.g. an alkali metal alkoxide such as sodium methoxide,
sodium ethoxide or potassium tertiary butoxide; a
carbonate such as sodium carbonate or potassium
carbonate; a bicarbonate such as sodium bicarbonate or
potassium bicarbonate; a metal hydroxide such as sodium
hydroxide or potassium hydroxide; a metal hydride such as
sodium hydride or potassium hydride; an amine such as
monomethylamine, dimethylamine or triethylamine; and a
pyridine such as pyridine or 4-dimethylaminopyridine.
The base may be used in an amount of from 1 to 2 mols,
preferably from 1 to 1.5 mols, per mol of the compound of
the formula (I-10).
The solvent may be any solvent so long as it is a
solvent inert to the reaction. For example, it may be
one or more suitably selected from e.g. an aromatic
hydrocarbon such as benzene, toluene, xylene or
chlorobenzene; an aliphatic hydrocarbon such as carbon
tetrachloride, methyl chloride, chloroform,
dichloromethane, dichloroethane, trichloroethane, hexane
or cyclohexane; an ether such as dioxane, tetrahydrofuran,
diethyl ether or dimethoxyethane; an ester such as methyl

acetate or ethyl acetate; a polar aprotic solvent such as
dimethyl sulfoxide, sulfolane, dimethylacetamide,
dimethylformamide, N-methylpyrrolidone or pyridine; a
nitrile such as acetonitrile, propionitrile or
acrylonitrile; and a ketone such as acetone or methyl
ethyl ketone.
The reaction temperature for reaction (K) is usually
from -20 to 100°C, preferably from 0 to 50°C. The
reaction time is usually from 0.1 to 24 hours, preferably
from 0.1 to 12 hours.
The compound of the formula (II) to be used in the
above reaction (A) or (C) can be produced by the
following reactions (L) to (N).

In reaction (L), A, R1 and R2 are as defined above.
In reaction (L), a salt of the compound (II) can be
produced by post treatment of the reaction or in
accordance with a usual reaction for forming a salt.
Reaction (L) may be carried out usually in the
presence of an oxidizing agent and a solvent.
The oxidizing agent may, for example, be potassium
ferricyanide. The oxidizing agent may be used in an

amount of from 1 to 10 mols, preferably from 1 to 5 mols,
per mol of the compound of the formula (XII).
The solvent may be any solvent so long as it is inert
to the reaction. For example, it may be one or more
suitably selected from e.g. an ether such as dioxane,
tetrahydrofuran, diethyl ether or dimethoxyethane; an
ester such as methyl acetate or ethyl acetate; a polar
aprotic solvent such as dimethyl sulfoxide, sulfolane,
dimethylacetamide, dimethylformamide, N-methylpyrrolidone,
pyridine, acetonitrile or propionitrile; and a ketone
such as acetone or methyl ethyl ketone.
The reaction temperature for reaction (L) is usually
from 20 to 150°C, preferably from 50 to 100°C. The
reaction time is usually from 0.5 to 3 0 hours, preferably
from 1 to 20 hours.

In reaction (M), A, R1 and R2 are as defined above.
In reaction (M) , a salt of the compound (II) can be
produced by post treatment of the reaction or in
accordance with a usual reaction for forming a salt.
The cyclization reaction in reaction (M) may be
carried out usually in the presence of a base and a

solvent.
The base may be one or more suitably selected from
e.g. an alkali metal such as sodium or potassium; an
alkali metal alkoxide such as sodium methoxide, sodium
ethoxide or potassium tert-butoxide; and a metal hydride
such as sodium hydride or potassium hydride. The base
may be used in an amount of from 1 to 3 mols, preferably
from 1 to 1.5 mols per mol of the compound of the formula
(XIII).
The solvent may be any solvent so long as it is inert
to the reaction. For example, it may be one or more
suitably selected from e.g. an aromatic hydrocarbon such
as benzene, toluene, xylene or chlorobenzene; an ether
such as dioxane, tetrahydrofuran, diethyl ether or
dimethoxyethane; an alcohol such as methanol, ethanol,
propanol or tert-butanol; and a nitrile such as
acetonitrile, propionitrile or acrylonitrile.
The reaction temperature for the cyclization reaction
in reaction (M) is usually from 0 to 150°C, preferably
from 30 to 100oC. The reaction time is usually from 0.5
to 24 hours, preferably from 1 to 12 hours.
The hydrolytic reaction in reaction (M) may be
carried out in accordance with a common hydrolytic
reaction and may be carried out usually in the presence
of an acid or base and a solvent.
The acid may, for example, be hydrogen chloride or
sulfuric acid. The base may, for example, be a metal

hydroxide such as sodium hydroxide or potassium hydroxide.
The solvent may be any solvent so long as it is inert
to the reaction. For example, it may be one or more
suitably selected e.g. an alcohol such as methanol,
ethanol, propanol or tert-butanol; a nitrile such as
acetonitrile, propionitrile or acrylonitrile; a ketone
such as acetone or methyl ethyl ketone; and water.
The reaction temperature for the hydrolytic reaction
in reaction (M) is usually from 0 to 100°C, preferably
from 20 to 80°C. The reaction time is usually from 0.1
to 12 hours, preferably from 0.1 to 1 hour.

In reaction (N), A, R1 and R2 are as defined above.
In reaction (N), a salt of the compound (II) can be
produced by post treatment of the reaction or in
accordance with a usual reaction for forming a salt.
The reduction reaction in reaction (N) may, for
example, be catalytic reduction, reduction by a metal
hydride (such as sodium boron hydride, or lithium
aluminum hydride); reduction by e.g. triphenylphosphine,
dimethyl sulfide or diphenyl sulfide; or reduction in a
reaction system constituted by a metal such as iron or
copper and a carboxylic acid such as formic acid or

acetic acid. The catalytic reduction is usually carried
out in a hydrogen atmosphere by using a catalyst, such as
platinum, platinum oxide, platinum black, Raney Nickel,
palladium, palladium-carbon, rhodium or rhodium-alumina.
Reaction (N) may be carried out usually in the
presence of a solvent. The solvent may be any solvent so
long as it is a solvent inert to the reaction. For
example, it may be one or more suitably selected from e.g.
an aromatic hydrocarbon such as benzene, toluene or
xylene; an aliphatic hydrocarbon such as hexane or
cyclohexane; an ether such as dioxane, tetrahydrofuran,
diethyl ether or dimethoxyethane; an ester such as methyl
acetate or ethyl acetate; a polar aprotic solvent such as
dimethyl sulfoxide, sulfolane, dimethylacetamide,
dimethylformamide, N-methylpyrrolidone, pyridine,
acetonitrile or propionitrile; a ketone such as acetone
or methyl ethyl ketone; an alcohol such as methanol,
ethanol, propanol or tert-butanol; and water.
The reaction temperature in reaction (N) is usually
from 0 to 150°C, preferably from 0 to 80DC. The reaction
time is usually from 0.5 to 96 hours, preferably from 1
to 48 hours.
The compound of the formula (XIII) to be used in the
above reaction (M) can be produced by the following
reaction (O).


In reaction (O), A, R1 and R2 are as defined above.
Reaction (O) may be carried out, if necessary, in the
presence of a solvent. The solvent may be any solvent so
long as it is inert to the reaction, and for example, it
may be one or more suitably selected from e.g. an
aromatic hydrocarbon such as benzene, toluene, xylene or
chlorobenzene; an aliphatic hydrocarbon such as carbon
tetrachloride, chloroform, dichloromethane,
dichloroethane, trichloroethane, hexane or cyclohexane;
an ether such as dioxane, tetrahydrofuran, diethyl ether
or dimethyoxyethane; an ester such as methyl acetate or
ethyl acetate; an alcohol such as methanol, ethanol,
propanol or tert-butanol; a polar aprotic solvent such as
acetonitrile, propionitrile or acrylonitrile; and a
ketone such as acetone or methyl ethyl ketone.
Methyl iodide in reaction (O) may be used in an
amount of from 1 to 10 mols, preferably from 1 to 3 mols,
per mol of the compound of the formula (XV) . Further,
methyl iodide may serve also as a solvent if used
excessively.
The reaction temperature for reaction (O) is usually
from 0 to 100°C, preferably from 10 to 50°C. The reaction

time is usually from 0.5 to 48 hours, preferably from 1
to 24 hours.
The compound of the formula (XIV) to be used in the
above reaction (N) can be produced by the following
reaction (P).

In reaction (P), A, R1 and R2 are as defined above, U
is an atom of chlorine or bromine.
Reaction (P) may be carried out in the presence of an
azidation agent. The azidation agent may be one or more
suitably selected from e.g. sodium azide, potassium azide
and trimethylsilyl azide.
Reaction (P) may be carried out usually in the
presence of a solvent. The solvent may be any solvent so
long as it is a solvent inert to the reaction. For
example, it may be one or more suitably selected from e.g.
an aromatic hydrocarbon such as benzene, toluene, xylene
or chlorobenzene; an aliphatic hydrocarbon such as carbon
tetrachloride, chloroform, dichloromethane,
dichloroethane, trichloroethane, hexane or cyclohexane;
an ether such as dioxane, tetrahydrofuran, diethyl ether
or dimethoxyethane; an ester such as methyl acetate or
ethyl acetate; a polar aprotic solvent such as dimethyl

sulfoxide, sulfolane, dimethylacetamide,
dimethylformamide, N-methylpyrrolidone, pyridine,
acetonitrile or propionitrile; a ketone such as acetone
or methyl ethyl ketone; an alcohol such as methanol,
ethanol, propanol or tert-butanol; and water.
The reaction temperature for reaction (P) is usually
from 0 to 150°C, preferably from 20 to 90°C. The reaction
time is usually from 0.1 to 96 hours, preferably from 0.5
to 12 hours.
The compound of the formula (XV) to be used in the
above reaction (O) can be produced by the following
reaction (Q).

In reaction (Q), A, R1 and R2 are as defined above.
Reaction (Q) can be carried out in accordance with a
common hydrazone synthetic reaction and, if necessary, in
the presence of a dehydrating agent and/or a catalyst.
As the dehydrating agent, molecular sieve may, for
example, be mentioned. The dehydrating agent may be used
usually from 1 to 3 0 times, preferably from 5 to 10 times
relative to the weight of the compound of the formula
(XII).
The catalyst may, for example, be titanium
tetrachloride.

Dimethylhydrazine for reaction (Q) may be used
usually in an amount of from 1 to 3 0 mols, preferably
from 5 to 10 mols, per mol of the compound of the formula
(XII).
The reaction temperature for reaction (Q) is
usually from 20 to 150°C, preferably from 50 to 120°C.
The reaction time is usually from 5 to 2 00 hours,
preferably from 24 to 120 hours.
The compound of the formula (XVI) to be used in the
above reaction (P) can be produced by the following
reaction (R).

In reaction (R), A, R1, R2 and U are as defined
above.
Reaction (R) may be carried out in the presence of a
chlorination agent or a bromination agent. The
chlorination agent may be one or more suitably selected
from e.g. chlorine and N-chlorosuccinimide. The
bromination agent may be one or more suitably selected
from e.g. bromine, N-bromosuccinimide and phenyltrimethyl
ammonium tribromide.
Reaction (R) may be carried out usually in the
presence of a solvent. The solvent may be any solvent so
long as it is a solvent inert to the reaction. For

example, it may be one or more suitably selected from e.g.
an aliphatic hydrocarbon such as carbon tetrachloride,
methyl chloride, chloroform, dichloromethane,
dichloroethane, trichloroethane, hexane or cyclohexane;
an ether such as dioxane, tetrahydrofuran, diethyl ether
or dimethoxyethane; an ester such as methyl acetate or
ethyl acetate; a polar aprotic solvent such as dimethyl
sulfoxide, sulfolane, dimethylacetamide,
dimethylformamide, N-methylpyrrolidone or pyridine; an
organic acid such as acetic acid or propionic acid; and
water.
Reaction (R) may be carried out, if necessary, in the
presence of a base or an acid.
The base may, for example, be lithium
diisopropylamide. The base is used in an amount of from
1 to 2 mols, preferably from 1 to 1.2 mols, per mol of
the compound of the formula (XII).
When the reaction is carried out in the presence of a
base, the solvent may usually be one or more suitably
selected from ethers such as tetrahydrofuran and diethyl
ether.
The acid may be one or more suitably selected from
e.g. an organic acid such as acetic acid or propionic
acid, and aluminum chloride. The acid is usually used in
a catalytic amount. Further, an organic acid as a
solvent may serve as both a solvent and an acid if used
excessively.


In reaction (S) , R1 and R2 are as defined above, and
Z is an oxygen atom or -C{G1)G2-, Xa is an hydrogen atom,
chlorine atom or alkyl, Xa' is a chlorine atom or alkyl,
each of Xb, Xc, Xd, Xe, G1 and G2 is an atom of hydrogen,
fluorine or chlorine, V is an atom of bromine or iodine,
and j is 0 or 1.
The first step in reaction (S) may be carried out in
the presence of a base and a solvent.
The base may be suitably selected from an organic
lithium compound such as lithium diisopropylamide. The

base may be used in an amount of from 1 to 2 mols,
preferably from 1 to 1.5 mols, per mol of the compound of
the formula (XVII-1) or (XVII-2).
The solvent may be any solvent so long as it is a
solvent inert to the reaction. For example, it may be
one or more suitably selected from e.g. an ether such as
dioxane, tetrahydrofuran and diethyl ether.
The chlorination agent to be used for the first step
in reaction (S) may, for example, be N-chlorosuccinimide.
The formula: Xa'-I to be used for the first step in
reaction (S) may be used in an amount of from 1 to 10
mols, preferably from 1 to 5 mols, per mol of the
compound of the formula (XVII-1) or (XVII-2). Further,
the chlorination agent to be used for the first step in
reaction (S) is used in an amount of from 1 to 5 mols,
preferably from 1 to 3 mols, per mol of the compound of
the formula (XVII-1) or (XVII-2).
The first step in reaction (S) may be carried out, if
necessary, in the presence of an inert gas. The inert
gas may be suitably selected from e.g. nitrogen gas or
argon gas.
The reaction temperature for the first step in
reaction (S) is usually from -100 to 50°C, preferably
from -70 to 25°C. The reaction time is usually from 1 to
48 hours, preferably from 1 to 20 hours.
The second step in reaction (S) may be carried out,
usually in the presence of a base and a solvent.

The base may be one or more suitably selected from
e.g. organic lithium compounds such as methyllithium and
n-butyllithium; and Grignard compounds such as isopropyl
magnesium chloride. The base may be used in an amount of
from 1 to 2 mols, preferably from 1 to 1.5 mols, per mol
of the compound of the formula (XVII-1), (XVII-2),
(XVIII-1) or (XVIII-2).
The solvent may be any solvent so long as it is a
solvent inert to the reaction. For example, it may be
one or more suitably selected from e.g. an ether such as
dioxane, tetrahydrofuran and diethyl ether.
The compound of the formula (XIX) to be used for
the second step in reaction (S) is used in an amount of
from 1 to 3 mols, preferably from 1 to 1.5 mols, per mol
of the compound of the formula (XVII-1), (XVII-2),
(XVIII-1) or (XVIII-2).
The second step in reaction (S) may be carried out,
if necessary, in the presence of an inert gas. The inert
gas may be suitably selected from e.g. nitrogen gas and
argon gas.
The reaction temperature for the second step in
reaction (S) is usually from -100 to 50°C, preferably
from -70 to 25°C. The reaction time is usually from 1 to
48 hours, preferably from 1 to 2 0 hours.


In reaction (T) , R1 , R2 , Z, Xa , Xa ' , Xb , Xc , Xa , Xe ,
V and j are as defined above.
The first step in reaction (T) may be carried out
usually in the presence of a base and a solvent.
The base may be one or more suitably selected from
e.g. organic lithium compounds such as methyllithium and
n-butyllithium; and Grignard compounds such as isopropyl

magnesium chloride.
The base is used in an amount of from 1 to 2 moIs,
preferably from 1 to 1.5 mols, per mol of the compound of
the formula (XVII-1), (XVII-2), (XVIII-1) or (XVIII-2).
The solvent may be any solvent so long as it is a
solvent inert to the reaction. For example, it may be
one or more suitably selected from e.g. an ether such as
dioxane, tetrahydrofuran and diethyl ether.
The compound of the formula (XX) to be used for the
first step in reaction (T) is used in an amount of from 1
to 3 mols, preferably from 1 to 1.5 mols, per mol of the
compound of the formula (XVII-1), (XVII-2), (XVIII-1) or
(XVIII-2).
The first step in reaction (T) may be carried out, if
necessary, in the presence of an inert gas. The inert
gas may be suitably selected from e.g. nitrogen gas and
argon gas.
The reaction temperature for the first step in
reaction (T) is usually from -100 to 50°C, preferably
from -70 to 25°C. The reaction time is usually from 1 to
48 hours, preferably from 1 to 20 hours.
The second step for reaction (T) may be carried out
usually in the presence of an oxidizing agent and a
solvent.
The oxidizing agent may be one or more suitably
selected from e.g. pyridinium chlorochromate and
manganese dioxide. The oxidizing agent is used in an

amount of from 1 to 10 mols, preferably from 1 to 3 mols,
per mol of the compound of the formula (XXI-1) or (XXI-2).
The solvent may be any solvent so long as it is a
solvent inert to the reaction. For example, it may be
one or more suitably selected from e.g. an aromatic
hydrocarbon such as benzene, toluene, xylene or
chlorobenzene; and an aliphatic hydrocarbon such as
carbon tetrachloride, chloroform, dichloromethane,
dichloroethane, trichloroethane, hexane or cyclohexane.
The reaction temperature for the second step in
reaction (T) is usually from 0 to 150°C, preferably from
20 to 100°C. The reaction time is usually from 0.5 to 24
hours, preferably from 1 to 12 hours.

In reaction (U), A, B, R1, R2 and Z, are as defined
above.
Reaction (U) may be carried out in accordance with
the above reaction (A).


In reaction (V), A, B, R1, R2 , U and Z are as
defined above. Further, the thiocarbonylation agent,
may, for example, be a Lawesson reagent or diphosphorus
pentasulfide. Reaction (V) comprises five stage
reactions (1) to (5) as shown in the above flow process,
and the reaction conditions of the respective reactions
will be described below.
The reaction (1) may usually be carried out in the
presence of a solvent. The solvent may be any solvent
inert to the reaction, and it may be one or more suitably
selected from aromatic hydrocarbons such as benzene,
toluene and xylene; aliphatic hydrocarbons such as
pentane, hexane, heptane, petroleum ether, ligroin and
petroleum benzin; ethers such as diethyl ether, dipropyl
ether, dibutyl ether, tetrahydrofuran, and dioxane; and
carbon disulfide.

The reaction (1) may usually be carried out at from
-20°C to 150°C, preferably from 0 to 110°C, and the
reaction time is usually from 0.1 to 48 hours.
In the reaction (1), the thiocarbonylation agent may
be used in an amount of from 0.4 to 2 mols, per mol of
the compound of the formula (XII).
The reaction (2) can be carried out in accordance
with the above reaction (R).
The reaction (3) can be carried out in accordance
with the above reaction (P).
The reaction (4) can be carried out in accordance
with the above reaction (N).
The reaction (5) can be carried out in accordance
with the above reaction (A).

In reaction (W) , A, B, R1, R2 and Z are as defined
above.
Reaction (W) can be carried out in accordance with
the above reaction (A).
Further, the acid amide derivative of the formula
(I) or a salt thereof may be produced with reference to
the method disclosed in WO2001/60783 or WO2003/27059, as
the case requires.

A fungicidal composition containing an acid amide
derivative of the formula (I) or a salt thereof as an
active ingredient (hereinafter referred to simply as the
composition of the present invention) is capable of
controlling noxious fungi at a low dose and thus useful,
for example, as an agricultural or horticultural
fungicidal composition.
BEST MODE FOR CARRYING OUT THE INVENTION
Now, preferred embodiments of the composition of the
present invention will be described.
The composition of the present invention is useful
as a fungicidal composition capable of controlling
noxious fungi at a low dose, particularly useful as an
agricultural or horticultural fungicidal composition.
When used as an agricultural or horticultural fungicidal
composition, the composition of the present invention is
capable of controlling noxious fungi such as Oomycetes,
Ascomycetes, Basidiomycetes, Deuteromycetes and
particularly effective for controlling noxious fungi
belonging to e.g. Ascomycetes or Deuteromycetes.
The following may be mentioned as specific examples
of the above noxious fungi.
Oomycetes may, for example, be genus Phytophthora,
such as potato or tomato late blight pathogen
(Phytophthora infestans), or tomato haiiro-eki-byo
pathogen (Phytophthora capsici); genus Pseudoperonospora,

such as cucumber downy mildew pathogen (Pseudoperonospora
cubensis); genus Plasmopara, such, as grape downy mildew
pathogen (Plasmopara viticola); and genus Pythium, such
as rice seedling blight pathogen (Pythium graminicola),
or wheat browning root rot pathogen (Pythium iwayamai).
Ascomycetes may, for example, be genus Erysiphe,
such as wheat powdery mildew pathogen (Erysiphe
graminis); genus Sphaerotheca, such as cucumber powdery
mildew pathogen (Sphaerotheca fuliginea), or strawberry
powdery mildew pathogen (Sphaerotheca humuli); genus
Uncinula, such as grape powdery mildew pathogen (Uncinula
necator); genus Podosphaera, such as apple powdery mildew
pathogen (Podosphaera leucotricha); genus Mycosphaerella,
such as garden pea Mycosphaerella blight pathogen
(Mycosphaerella pinodes), apple fruit spot pathogen
(Mycosphaerella pomi), banana black sigatoka pathogen
(Mycosphaerella musicola), persimmons circular leaf spot
pathogen (Mycosphaerella nawae), or strawberry leaf spot
pathogen (Mycosphaerella fragariae); genus Venturia, such
as apple scab pathogen (Venturia inaequalis) , or pear
scab pathogen (Venturia nashicola); genus Pyrenophora,
such as barley net blotch pathogen (Pyrenophora teres),
or barley stripe pathogen (Pyrenophora graminea); genus
Sclerotinia, such as various Sclerotinia disease pathogen
(Sclerotinia Sclerotiorum) such as kidney bean stem rot
pathogen, cucumber Sclerotinia rot pathogen, cabbage
Sclerotinia rot pathogen, Chinese cabbage Sclerotinia rot

pathogen, red pepper Sclerotinia rot pathogen, sweet
pepper Sclerotinia rot pathogen, or onion watery soft rot
pathogen, wheat Sclerotinia snow blight pathogen
(Sclerotinia borealis), tomato syoryu-kinkaku pathogen
(Sclerotinia minor), or alfalfa Sclerotinia rot and crown
rot pathogen (Sclerotinia trifoliorum); genus
Botryolinia, such as peanut small Sclerotinia rot
pathogen (Botryolinia arachidis); genus Cochliobolus,
such as rice brown spot pathogen (Cochliobolus
miyabeanus); genus Didymella, such as cucumber gummy stem
blight pathogen (Didymella bryoniae); genus Gibberella,
such as wheat Fusarium blight pathogen (Gibberella zeae);
genus Elsinoe, such as grape anthracnose pathogen
(Elsinoe ampelina), or citrus scab pathogen (Elsinoe
fawcettii); genus Diaporthe, such as citrus melanose
pathogen (Diaporthe citri), or grape swelling arm
pathogen (Diaporthe sp.),- genus Monilinia, such as apple
blossom blight pathogen (Monilinia mali), or peach brown
rot pathogen (Monilinia fructicola); and genus
Glomerella, such as grape ripe rot pathogen (Glomerella
cingulata).
Basidiomycetes may, for example, be genus
Rhizoctonia, such as rice sheath blight pathogen
(Rhizoctonia solani); genus Ustilago, such as wheat loose
smut pathogen (Ustilago nuda); genus Puccinia, such as
oat crown rust pathogen (Puccinia coronata), wheat brown
rust pathogen (Puccinia recondita), or wheat stripe rust

pathogen (Puccinia striiformis); and genus Typhula, such
as wheat or barley Typhula snow blight pathogen (Typhula
incarnata, Typhula ishikariensisis).
Deuteromycetes may, for example, be genus Septoria,
such as wheat glume blotch pathogen (Septoria nodorum),
wheat speckled leaf blotch (Septoria tritici); genus
Botrytis, such as various gray mold pathogen (Botrytis
cinerea) such as grape gray mold pathogen, citrus gray
mold pathogen, cucumber gray mold pathogen, tomato gray
mold pathogen, strawberry gray mold pathogen, eggplant
gray mold pathogen, kidney bean gray mold pathogen,
adzuki bean gray mold pathogen, garden pea gray mold
pathogen, peanut gray mold pathogen, red pepper gray mold
pathogen, sweet pepper gray mold pathogen, lettuce gray
mold pathogen, onion gray mold pathogen, statice gray
mold pathogen, carnation gray mold pathogen, rose
Botrytis blight pathogen, garden pansy gray mold
pathogen, or sunflower gray mold pathogen, onion gray
mold neck rot pathogen (Botrytis allii), or onion
Botrytis hagare-syo (Botrytis squamosa, Botrytis
byssoidea, Botrytis tulipae); genus Pyricularia, such as
rice blast pathogen (Pyricularia oryzae); genus
Cercospora, such as sugar beet Cercospora leaf spot
pathogen (Cercospora beticola), or persimmons Cercospora
leaf spot pathogen (Cercospora kakivola); genus
Colletotrichum, such as cucumber anthracnose pathogen
(Colletotrichum orbiculare); genus Alternaria, such as

apple Alternaria leaf spot pathogen (Alternaria alternata
apple pathotype), pear black spot pathogen (Alternaria
alternata Japanese pear pathotype), potato or tomato
early blight pathogen (Alternaria solani), cabbage or
Chinese cabbage Alternaria leaf spot pathogen (Alternaria
brassicae), cabbage Alternaria sooty spot pathogen
(Alternaria brassicola), onion or Welsh onion Alternaria
leaf spot pathogen (Alternaria porri); genus
Pseudocercosporella, such as wheat eye spot pathogen
(Pseudocercosporella herpotrichoides); genus
Pseudocercospora, such as grape leaf spot pathogen
(Pseudocercospora vitis); genus Rhynchosporium, such as
barley scold pathogen (Rhynchosporium secalis); genus
Cladosporium, such as peach scab pathogen (Cladosporium
carpophilum); genus Phomopsis, such as peach Phomopsis
rot pathogen (Phomopsis sp.); genus Gloeosporium, such as
persimmons anthracnose pathogen (Gloeosporium kaki) ,-
genus Fulvia, such as tomato leaf mold pathogen (Fulvia
fulva); and genus Corynespora, such as cucumber
Corynespora leaf spot pathogen (Corynespora cassiicola).
The composition of the present invention is capable
of controlling the above various noxious fungi and thus
capable of preventively or curatively controlling various
diseases. Particularly, the composition of the present
invention is effective for controlling various diseases
which are problematic in the agricultural and
horticultural field, such as blast, brown spot, sheath

blight or damping-off of rice (Oryza sativa, etc.);
powdery mildew, scab, brown rust, stripe rust, net
blotch, stripe, snow mold, snow blight, loose smut, eye
spot, scald, leaf spot or glume blotch of cereals
(Hordeum vulgare, Tricum aestivum, etc.); melanose or
scab of citrus (Citrus spp., etc.); blossom blight,
powdery mildew, melanose, Alternaria leaf spot or scab of
apple (Malus pumila); scab or black spot of pear (Pyrus
serotina, Pyrus ussuriensis, Pyrus communis); brown rot,
scab or Phomopsis rot of peach (Prunus persica, etc.);
anthracnose, ripe rot, leaf spot, swelling arm, powdery
mildew or downy mildew of grape (Vitis vinifera spp.,
etc.); anthracnose, circular leaf spot or Cercospora leaf
spot of Japanese persimmon (Diospyros kaki, etc.);
anthracnose, powdery mildew, gummy stem blight,
corynespora leaf spot or downy mildew of cucurbit
(Cucumis melo, etc.); early blight, haiiro-eki-byo, leaf
mold or late blight of tomato (Lycopersicon esculentum);
black sigatoka of banana (Musa sapientum, etc.);
Cercospora leaf spot of sugar beet (Beta vulgaris var.
saccharifera, etc.); Mycosphaerella blight of garden pea
(Pisum sativum); various Alternaria disease pathogens of
cruciferous vegetables (Brassica sp., Raphanus sp., etc) ;
late blight or early blight of potato (Solanum
tuberosum); powdery mildew or leaf spot of strawberry
(Fragaria, etc.); and gray mold or disease caused by
Sclerotinia of various crops such as beans, vegetables,

fruits or flowers. Among them, it is particularly-
effective against various gray mold or disease caused by
Sclerotinia of cucumber (Cucumis sativus)-, kidney bean
(Phaseolus vulgaris), adzuki bean (Vigna angularis),
soybean (Glycine max), garden pea, peanut (Arachis
hypogaea), tomato, strawberry, eggplant (Solanum
melongena), red pepper (Capsicum annuum), sweet pepper
(Capsicum annuum), lettuce (Lactuca sativa), onion
(Allium cepa), grape, citrus, statice (Limonium spp.),
carnation (Dianthus spp.), rose (Rosa spp.), garden pansy
(Viola, etc.) or sunflower (Helianthus annuus).
Further, the composition of the present invention is
effective also for preventive or curative control of soil
diseases caused by plant pathogens such as Fusarium,
Pythium, Rhizoctonia, Verticillium and Plasmodiophora.
Still further, the composition of the present
invention is effective also to control various pathogens
resistant to fungicides such as benzimidazoles,
strobilurins, dicarboximides, phenylamides and ergosterol
biosynthesis inhibitors.
Furthermore, the composition of the present
invention has an excellent penetrative migration
property, and when a pesticide containing the composition
of the present invention is applied to soil, it is
possible to control noxious fungi on stems and leaves at
the same time as controlling noxious fungi in soil.
The composition of the present invention, is usually

formulated by mixing the acid amide derivative
represented by the formula (I) or a salt thereof with
-various agricultural adjuvants and used in the form of a
formulation such as a dust, granules, water-dispersible
granules, a wettable powder, a water-based suspension
concentrate, an oil-based suspension concentrate, water
soluble granules, an emulsifiable concentrate, a soluble
concentrate, a paste, an aerosol or an ultra low-volume
formulation. However, so long as it is suitable for the
purpose of the present invention, it may be formulated
into any type of formulation which is commonly used in
this field. Such agricultural adjuvants include solid
carriers such as diatomaceous earth, slaked lime, calcium
carbonate, talc, white carbon, kaoline, bentonite, a
mixture of kaolinite and sericite, clay, sodium
carbonate, sodium bicarbonate, mirabilite, zeolite and
starch; solvents such as water, toluene, xylene, solvent
naphtha, dioxane, acetone, isophorone, methyl isobutyl
ketone, chlorobenzene, cyclohexane, dimethylsulfoxide,
N,N-dimethylformamide, dimethylacetamide, N-methyl-2-
pyrrolidone, and alcohol; anionic surfactants and
spreaders such as a salt of fatty acid, a benzoate, an
alkylsulfosuccinate, a dialkylsulfosuccinate, a
polycarboxylate, a salt of alkylsulfuric acid ester, an
alkyl sulfate, an alkylaryl sulfate, an alkyl diglycol
ether sulfate, a salt of alcohol sulfuric acid ester, an
alkyl sulfonate, an alkylaryl sulfonate, an aryl

sulfonate, a lignin sulfonate, an alkyldiphenyl ether
disulfonate, a polystyrene sulfonate, a salt of
alkylphosphoric acid ester, an alkylaryl phosphate,, a
styrylaryl phosphate, a salt of polyoxyethylene alkyl
ether sulfuric acid ester, a polyoxyethylene alkylaryl
ether sulfate, a salt of polyoxyethylene alkylaryl ether
sulfuric acid ester, a polyoxyethylene alkyl ether
phosphate, a salt of polyoxyethylene alkylaryl phosphoric
acid ester, and a salt of a condensate of naphthalene
sulfonate with formalin; nonionic surfactants and
spreaders such as a sorbitan fatty acid ester, a glycerin
fatty acid ester, a fatty acid polyglyceride, a fatty
acid alcohol polyglycol ether, acetylene glycol,
acetylene alcohol, an oxyalkylene block polymer, a
polyoxyethylene alkyl ether, a polyoxyethylene alkylaryl
ether, a polyoxyethylene styrylaryl ether, a
polyoxyethylene glycol alkyl ether, a polyethylene
glycol, a polyoxyethylene fatty acid ester, a
polyoxyethylene sorbitan fatty acid ester, a
polyoxyethylene glycerin fatty acid ester, a
polyoxyethylene hydrogenated castor oil, and a
polyoxypropylene fatty acid ester; and vegetable and
mineral oils such as olive oil, kapok oil, castor oil,
palm oil, camellia oil, coconut oil, sesame oil, corn
oil, rice bran oil, peanut oil, cottonseed oil, soybean
oil, rapeseed oil, linseed oil, tung oil, and liquid
paraffins. Each of the components as such adjuvants may

be one or more suitable selected for use, so long as the
purpose of the present invention can thereby be
accomplished. Further, various additives which are
commonly used, such as a filler, a thickener, an anti-
settling agent, an anti-freezing agent, a dispersion
stabilizer, a phytotoxicity reducing agent, and an anti-
mold agent, may also be employed.
The weight ratio of the acid amide derivative
represented by the formula (I) or a salt thereof to the
various agricultural adjuvants is usually from
0.001:99.999 to 95:5, preferably from 0.005:99.995 to
90:10.
In the actual application of such a formulation, it
may be used as it is, or may be diluted to a
predetermined concentration with a diluent such as water,
and various spreaders e.g. surfactants, vegetable oils or
mineral oils may be added thereto, as the case requires.
The application of the composition of the present
invention can not generally be defined, as it varies
depending upon the weather conditions, the type of the
formulation, the crop plants to be treated, the
application season, the application site, the types or
germination states of noxious fungi, and the types or
degree of outbreak of the diseases. However, it is
usually applied in a concentration of the active
ingredient being from 0.1 to 10,000 ppm, preferably from
1 to 2,000 ppm in the case of foliage treatment, and its

dose may be such that the acid amide derivative of the
formula (I) or a salt thereof is usually from 0.1 to
50,000 g, preferably from 1 to 30,000 g, per hectare. In
the case of soil treatment, it is applied usually in such
a dose that the acid amide derivative of the formula (I)
or a salt thereof is from 10 to 100,000 g, preferably
from 200 to 20,000 g, per hectare.
The formulation containing the composition of the
present invention or a diluted product thereof may be
applied by an application method which is commonly used,
such as spreading (spreading, spraying, misting,
atomizing, grain diffusing or application on water
surface), soil application (such as mixing or irrigation)
or surface application (such as coating, dust coating or
covering). Further, it may be applied also by so-called
ultra low volume. In this method, the formulation may
contain 100% of the active ingredient.
The composition of the present invention may be
mixed with or may be used in combination with other
agricultural chemicals, fertilizers or phytotoxicity-
reducing agents, whereby synergistic effects or
activities may sometimes be obtained. Such other
agricultural chemicals may, for example, be a herbicide,
an insecticide, a miticide, a nematicide, a soil
pesticide, a fungicide, an antivirus agent, an
attractant, an antibiotic, a plant hormone and a plant
growth regulating agent. Especially, with a mixed

fungicidal composition having the acid amide derivative
of the formula (I) or a salt thereof mixed with or used
in combination with one or more of other fungicidally
active ingredient compounds, the application range, the
application time, the fungicidal activities, etc. may be
improved to preferred directions. Here, the acid amide
derivative of the formula (I) or a salt thereof, and the
active ingredient compound of another fungicide may
separately be formulated so that they may be mixed for
use at the time of application, or they may be formulated
together for use. The present invention includes such a
mixed fungicidal composition.
The mixing ratio of the acid amide derivative of the
formula (I) or a salt thereof to another fungicidally
active ingredient compound can not generally be defined,
since it varies depending upon the weather conditions,
the types of formulations, the crops to be treated, the
application time, the application site, the types or
germination state of noxious fungi, the types or state of
the diseases, etc., but it is usually within a range of
from 1:300 to 300:1, preferably from 1:100 to 100:1, by
weight. Further, the dose for the application may be
such that the total amount of the active compounds is
from 0.1 to 70,000 g, preferably from 1 to 30,000 g, per
hectare. The present invention includes a method for
controlling noxious fungi by an application of such a
mixed fungicidal composition.

The active ingredient compound (common name;
including some which are under application or test code
of the Japan, plant protection association) of the
fungicide in such another agricultural chemical, may, for
example, be:
an anilinopyrimidine compound such as Mepanipyrim,
Pyrimethanil or Cyprodinil;
a pyridinamine compound such as Fluazinam;
an azole compound such as Triadimefon, Bitertanol,
Triflumizole, Etaconazole, Propiconazole, Penconazole,
Flusilazole, Myclobutanil, Cyproconazole, Tebuconazole,
Hexaconazole, Furconazole-cis, Prochloraz, Metconazole,
Epoxiconazole, Tetraconazole, Oxpoconazole fumarate,
Sipconazole, Prothioconazole, Triadimenol, Flutriafol,
Difenoconazole, Fluquinconazole, Fenbuconazole,
Bromuconazole, Diniconazole, Tricyclazole, Probenazole or
Simeconazole, Pefurazoate, Ipconazole or Imibenconazole;
a quinoxaline compound such as Quinomethionate;
a dithiocarbamate compound such as Maneb, Zineb,
Mancozeb, Polycarbamate, Metiram or Propineb;
an organic chlorine compound such as Fthalide,
Chlorothalonil or Quintozene;
an imidazole compound such as Benomyl, Thiophanate-
Methyl, Carbendazim or Cyazofamid;
a cyano acetamide compound such as Cymoxanil;
a phenylamide compound such as Metalaxyl, Metalaxyl
M, Oxadixyl, Ofurace, Benalaxyl, Benalaxyl M, Furalaxyl

or Cyprofuram;
a sulfenic acid compound such as Dichlofluanid;
a copper compound such as Cupric hydroxide or Oxine
Copper;
an isoxazole compound such as Hymexazol;
an organic phosphorus compound such as Fosetyl-Al,
Tolcofos-Methyl, S-benzyl O,O-
diisopropylphosphorothioate, O-ethyl S,S-
diphenylphosphorodithioate or aluminum ethylhydrogen
phosphonate;
an N-halogenothioalkyl compound such a Captan,
Captafol or Folpet;
a dicarboxyimide compound such as Procymidone,
Iprodione or Vinclozolin;
a benzanilide compound such as Flutolanil, Mepronil,
Zoxamid or Tiadinil;
an anilide compound such as Boscalid;
a piperazine compound such as Triforine;
a pyridine compound such as Pyrifenox;
a carbinol compound such as Fenarimol or Flutriafol;
a piperidine compound such as Fenpropidine;
a morpholine compound such as Fenpropimorph or
Tridemorph;
an organic tin compound such as Fentin Hydroxide or
Fentin Acetate;
an urea compound such as Pencycuron;
a cinnamic acid compound such as Dimethomorph or

Flumorph;
a phenylcarbamate compound such as Diethofencarb;
a cyanopyrrole compound such as Fludioxonil or
Fenpiclonil;
a strobilurin compound such as Azoxystrobin,
Kresoxim-Methyl, Metominofen, Trifloxystrobin,
Picoxystrobin, Oryzastrobin, Dimoxystrobin,
Pyraclostrobin, Fluoxastrobin or Fluacrypyrin;
an oxazolidinone compound such as Famoxadone;
a thiazolecarboxamide compound such as Ethaboxam;
a silylamide compound such as Silthiopham;
an amino acid amide carbamate compound such, as
Iprovalicarb or Benthiavalicarb-isopropyl;
an imidazolidine compound such as Fenamidone;
a hydroxyanilide compound such as Fenhexamid;
a benzenesulfonamide compound such as Flusulfamide;
an oxime ether compound such as Cyflufenamid;
a phenoxyamide compound such as Fenoxanil;
an antibiotic such as Polyoxins;
a guanidine compound such as Iminoctadine;
other compound, such as Isoprothiolane, Pyroquilon,
Diclomezine, Quinoxyfen, Propamocarb Hydrochloride,
Spiroxamine Chloropicrin, Dazomet, Metam-sodium,
Nicobifen, Metrafenone, MTF-753 (Pentiopyrad), UBF-307,
Diclocymet, Proguinazid, NC-224 (Amibromdole,
Amisulbrom), KIF-7767 (KUF-1204, Pyribencarb methyl,
Mepyricarb) or Syngenta 446510 (Mandipropamid,

Dipromandamid).
The active ingredient compound (common name;
including some which are under application) of the
insecticide, miticide, nematicide or soil pesticide in
such another agricultural chemical, may, for example, be:
an organic phosphate compound such as Profenofos,
Dichlorvos, Fenamiphos, Fenitrothion, EPN, Diazinon,
Chlorpyrifos-methyl, Acephate, Prothiofos, Fosthiazate,
Phosphocarb, Cadusafos, Disulfoton, Chlorpyrifos,
Demeton-S-methyl, Dimethoate or Methamidophos;
a carbamate compound such as Carbaryl, Propoxur,
Aldicarb, Carbofuran, Thiodicarb, Methomyl, Oxamyl,
Ethiofencarb, Pirimicarb, Fenobucarb, Carbosulfan or
Benfuracarb;
a nelicetoxin derivative such as Cartap, Thiocyclam
or Bensultap;
an organic chlorine compound such as Dicofol or
Tetradifon;
an organic metal compound such as Fenbutatin Oxide;
a pyrethroid compound such as Fenvalerate,
Permethrin, Cypermethrin, Deltamethrin, Cyhalothrin,
Tefluthrin, Ethofenprox, Fenpropathrin or Bifenthrin;
a benzoyl urea compound such as Diflubenzuron,
Chlorfluazuron, Teflubenzuron, Flufenoxuron, Lufenuron or
Novaluron;
a juvenile hormone-like compound such as Methoprene,
Pyriproxyfen or Fenoxycarb;

a pyridadinone compound such as Pyridaben;
a pyrazole compound such as Fenpyroximate, Fipronil,
Tebufenpyrad, Ethiprole, Tolfenpyrad, Acetoprole,
Pyrafluprole or Pyriprole;
a neonicotinoide such as Imidacloprid, Nitenpyram,
Acetamiprid, Thiacloprid, Thiamethoxam, Clothianidin or
Dinotefuran;
a hydrazine compound such as Tebufenozide,
Methoxyfenozide or Chromafenozide;
a dinitro compound, an organosulfur compound, an
urea compound, a triazine compound or a hydrazone
compound;
other compound, such as Flonicamid, Buprofezin,
Hexythiazox, Amitraz, Chlordimeform, Silafluofen,
Triazamate, Pymetrozine, Pyrimidifen, Chlorfenapyr,
Indoxacarb, Acequinocyl, Etoxazole, Cyromazine, 1,3-
dichloropropene, Diafenthiuron, Benclothiaz, Flufenerim,
Pyridalyl, Spirodiclofen, Bifenazate, Spiromesifen,
spirotetramat, Propargite, Clofentezine, Fluacrypyrim,
Metaflumizone, Flubendiamide or Cyflumetofen.
Further, a microbial pesticide such as a BT agent,
an insect pathogenic virus agent, entomopathogenic fugi
or nematophagous fugi;
an antibiotic such as Avermectin, Emamectin-
Benzoate, Milbemectin, Spinosad, Ivermectin or
Lepimectin;
a natural product such as Azadirachtin.

Preferred embodiments of the present invention are
as follows. However, it should be understood that the
present invention is by no means restricted to such
specific embodiments.
(1) An acid amide derivative of the above formula
(I) or a salt thereof.
(2) The acid amide derivative of the above formula
(I) or a salt thereof, wherein A is phenyl which may be
substituted by X, naphthyl which may be substituted by X,
heterocyclic ring which may be substituted by X, or fused
heterocyclic ring which may be substituted by X; B is
heterocyclic ring (excluding pyridyl) which may be
substituted by Y, fused heterocyclic ring which may be
substituted by Y, or naphthyl which may be substituted by
Y; X is halogen, alkyl (the alkyl may be substituted by
halogen, hydroxy, alkoxy, haloalkoxy, alkylthio,
alkylsulfonyl, cycloalkyl, amino, monoalkylamino,
dialkylamino, cyano, alkoxycarbonyl, or
alkylcarbonyloxy), alkenyl, haloalkenyl, alkynyl (the
alkynyl may be substituted by halogen, hydroxy, alkoxy,
amino, hydroxycarbonyl, alkoxycarbonyl, or
trialkylsilyl), hydroxy, cyanooxy, alkoxy (the alkoxy may
be substituted by halogen, alkoxy, haloalkoxy, alkylthio,
cycloalkyl, monoalkylamino, dialkylamino, cyano, or
heterocyclic ring), alkenyloxy, haloalkenyloxy,
. alkynyloxy, haloalkynyloxy, alkylthio (the alkylthio may
be substituted by halogen, cycloalkyl, or cyano),

alkenylthio, haloalkenylthio, alkynylthio,
haloalkynylthio, alkylsulfinyl, haloalkylsulfinyl,
alkylsulfonyl, haloalkylsulfonyl, cycloalkyl which may be
substituted by halogen, cycloalkyloxy which may be
substituted by halogen, cycloalkylthio which may be
substituted by halogen, cyano, nitro, formyl, phenyl (the
phenyl may be substituted by halogen, alkyl, haloalkyl,
or alkoxy), phenoxy which may be substituted by alkyl,
phenylthio which may be substituted by alkyl, phenylalkyl
which may be substituted by alkyl, phenylalkenyl which
may be substituted by alkyl, phenylalkynyl which may be
substituted by alkyl, phenylalkyloxy which may be
substituted by alkyl, phenylalkenyloxy which may be
substituted by alkyl, phenylalkynyloxy which may be
substituted by alkyl, phenylamino which may be
substituted by alkyl, -OR4, -SR5 , -NR6R7, -CO2R8,
-C(=O)NR8R9, -SO2NR8R9, -CH=NR10 , or heterocyclic ring
(the heterocyclic ring may be substituted by halogen,
alkyl, or alkylcarbonyl); Y is halogen, alkyl (the alkyl
may be substituted by halogen, alkoxy, haloalkoxy, amino,
monoalkylamino, or dialkylamino), alkenyl, alkynyl,
hydroxy, alkoxy, haloalkoxy, alkylthio, haloalkylthio,
alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl,
haloalkylsulfonyl, cycloalkyl, cyano, nitro, formyl,
-OR4, -NR6R7, -CO2R8 , -C(=O)NR8R9, -SO2NR8R9, or
-CH=NR10; each of R1 and R2 which are independent of each
other, is hydrogen, alkyl, haloalkyl, alkoxyalkyl,

alkenyl, alkynyl, or cycloalkyl, or R1 and R2 may
together form a 3- to 6-membered saturated carbon ring;
R3 is hydrogen, alkyl (the alkyl may be substituted by
halogen, alkoxy, haloalkoxy, alkylthio, amino,
monoalkylamino, dialkylamino, or cyano), alkenyl,
alkynyl, hydroxy, alkoxy, haloalkoxy, cycloalkyl,
cycloalkyloxy, cyano, formyl, -C(=W3)R11, -C (=W3 ) OR12 , or
-S(O)mR12 .
(3) The acid amide derivative or a salt thereof,
wherein A is phenyl which may be substituted by X,
naphthyl which may be substituted by X, heterocyclic ring
which may be substituted by X, or fused heterocyclic ring
which may be substituted by X; B is 5-membered
heterocyclic ring which may be substituted by Y,
pyrazinyl, or fused heterocyclic ring which may be
substituted by Y; X is halogen, alkyl, haloalkyl,
alkoxyalkyl, dialkylaminoalkyl, alkynyl,
trialkylsilylalkynyl, hydroxy, alkoxy, haloalkoxy,
alkoxyalkoxy, cycloalkyl, nitro, phenyl, phenylalkynyl,
pyridyloxy which may be substituted by haloalkyl,
alkylcarbonyloxy, alkylsulfonyloxy, or heterocyclic ring
(the heterocyclic ring may be substituted by halogen,
alkyl, or alkylcarbonyl); Y is halogen, alkyl, haloalkyl,
alkoxy, haloalkoxy, cycloalkyl, or formyl; each of R1 and
R2 which are independent of each other, is hydrogen, or
alkyl; R3 is hydrogen, alkyl, alkylcarbonyl, or
alkoxycarbonyl; and each of W1 and W2 which are

independent of each other, is oxygen or sulfur.
(4) The acid amide derivative or a salt thereof
according to the above (3), wherein each of W1 and W2 is
oxygen.
(5) The acid amide derivative or a salt thereof
according to the above (3), wherein B is fused
heterocyclic ring which may be substituted by Y.
(6) The acid amide derivative or a salt thereof
according to the above (5), wherein the fused
heterocyclic ring is benzofuranyl, dihydrobenzofuranyl,
benzodioxanyl or quinolyl.
(7) The acid amide derivative or a salt thereof
according to the above (3), wherein B is 5-membered
heterocyclic ring which may be substituted by Y; X is
halogen, alkyl, haloalkyl, alkynyl, hydroxy, alkoxy,
haloalkoxy, alkoxyalkdxy, cycloalkyl, nitro, phenylalkyl,
pyridyloxy which may be substituted by haloalkyl,
alkylcarbonyloxy, or heterocyclic ring (the heterocyclic
ring may be substituted by halogen, alkyl, or
alkylcarbonyl); Y is halogen, alkyl, haloalkyl, or
alkoxy; R3 is hydrogen, alkylcarbonyl, or alkoxycarbonyl;
and each of W1 and W2 is oxygen.
(8) The acid amide derivative or a salt thereof
according to the above (3) or (7), wherein B is furyl
which may be substituted by Y, thienyl which may be
substituted by Y, pyrrolyl which may be substituted by Y,
oxazolyl which may be substituted by Y, isoxazolyl which

may be substituted by Y, thiazolyl which may be
substituted by Y, isothiazolyl which may be substituted
by Y, pyrazolyl which may be substituted by Y, or
thiadiazolyl which may be substituted by Y.
(9) The acid amide derivative or a salt thereof
according to the above (8), wherein B is furyl which may
be substituted by Y, thienyl which may be substituted by
Y, pyrrolyl which may be substituted by Y, oxazolyl which
may be substituted by Y, thiazolyl which may be
substituted by Y, isothiazolyl which may be substituted
by Y, pyrazolyl which may be substituted by Y, or
thiadiazolyl which may be substituted by Y.
(10) The acid amide derivative or a salt thereof
according to the above (9), wherein B is furyl
substituted by Y.
(11) The acid amide derivative or a salt thereof
according to the above (9), wherein B is thienyl
substituted by Y.
(12) The acid amide derivative or a salt thereof
according to the above (9), wherein B is pyrazolyl
substituted by Y.

(13) An acid amide derivative of the above formula
(I-α) or a salt thereof.
(14) The acid amide derivative of the above formula
(I-α) or a salt thereof, wherein B is 5-membered
heterocyclic ring which may be substituted by Y,
pyrazinyl, or fused heterocyclic ring which may be

substituted by Y; Xa is fluorine, chlorine, iodine,
alkyl, haloalkyl, alkoxyalkyl, dialkylaminoalkyl,
alkynyl, trialkylsilylalkynyl, hydroxy, alkoxy,
haloalkoxy, alkoxyalkoxy, cycloalkyl, nitro, phenyl,
phenylalkynyl, pyridyloxy which may be substituted by
haloalkyl, alkylcarbonyloxy, alkylsulfonyloxy, or
heterocyclic ring (the heterocyclic ring may be
substituted by halogen, alkyl, or alkylcarbonyl); Y is
halogen, alkyl, haloalkyl, alkoxy, haloalkoxy,
cycloalkyl, or formyl; each of R1 and R2 which are
independent of each other, is hydrogen or alkyl; R3 is
hydrogen, alkyl, alkylcarbonyl, or alkoxycarbonyl; and
each of W1 and W2 which are independent of each other, is
oxygen, or sulfur.
(15) The acid amide derivative or a salt thereof
according to the above (14), wherein each of W1 and W2 is
oxygen.
(16) The acid amide derivative or a salt thereof
according to the above (14), wherein B is the fused
heterocyclic ring which may be substituted by Y.
(17) The acid amide derivative or a salt thereof
according to the above (16), wherein the fused
heterocyclic ring is benzofuranyl, dihydrobenzofuranyl,
benzodioxanyl or quinolyl.
(18) The acid amide derivative or a salt thereof
according to the above (14), wherein wherein B is 5-
membered heterocyclic ring which may be substituted by Y;

Xa is fluorine, chlorine, iodine, alkyl, haloalkyl,
alkynyl, hydroxy, alkoxy, haloalkoxy, alkoxyalkoxy,
cycloalkyl, n.itro, phenylalkynyl, pyridyloxy which may be
substituted by haloalkyl, alkylcarbonyloxy, or
heterocyclic ring (the heterocyclic ring may be
substituted by halogen, alkyl, or alkylcarbonyl); Y is
halogen, alkyl, haloalkyl, or alkoxy; R3 is hydrogen,
alkylcarbonyl, or alkoxycarbonyl; and each of W1 and W2
is oxygen.
(19) The acid amide derivative or a salt thereof
according to the above (14) or (18), wherein B is furyl
which may be substituted by Y, thienyl which may be
substituted by Y, pyrrolyl which may be substituted by Y,
oxazolyl which may be substituted by Y, isoxazolyl which
may be substituted by Y, thiazolyl which may be
substituted by Y, isothiazolyl which may be substituted
by Y, imidazolyl which may be substituted by Y, pyrazolyl
which may be substituted by Y, or thiadiazolyl which may
be substituted by Y.
(20) The acid amide derivative or a salt thereof
according to the above (19), wherein B is furyl which may
be substituted by Y, thienyl which may be substituted by
Y, pyrrolyl which may be substituted by Y, oxazolyl which
may be substituted by Y, isoxazolyl which may be
substituted by Y, thiazolyl which may be substituted by
Y, isothiazolyl which may be substituted by Y, pyrazolyl
which may be substituted by Y, or thiadiazolyl which may

be substituted by Y.
(21) The acid amide derivative or a salt thereof
according to the above (20), wherein B is furyl
substituted by Y.
(22) The acid amide derivative or a salt thereof
according to the above (20), wherein B is thienyl
substituted by Y.
(23) The acid amide derivative or a salt thereof
according to the above (20), wherein B is pyrazolyl
substituted by Y.
(24) The acid amide derivative or a salt thereof
according to the above (3) or (14), wherein A is phenyl
which may be substituted by X, naphthyl which may be
substituted by X, benzodioxolanyl which may be
substituted by X, or benzodioxanyl which may be
substituted by X; B is furyl which may be substituted by
Y, thienyl which may be substituted by Y, or pyrazolyl
which may be substituted by Y; X is halogen, alkyl,
haloalkyl, alkoxy, or haloalkoxy; Y is halogen, alkyl,
haloalkyl, alkoxy, or haloalkyl; R3 is hydrogen; and each
of W1 and W2 is oxygen.
(25) The acid amide derivative or a salt thereof
according to the above (24), wherein B is furyl
substituted by Y, thienyl substituted by Y, or pyrazolyl
substituted by Y.
(2 6) The acid amide derivative or a salt thereof
according to the above (24), wherein B is furyl

substituted by Y, thienyl substituted by Y, pyrazolyl
substituted by Y, and Y is halogen, alkyl or haloalkyl.
(27) The acid amide derivative or a salt thereof
according to the above (24), wherein A is phenyl
substituted by X, or benzodioxolanyl substituted by X,
and B is furyl substituted by Y, thienyl substituted by
Y, or pyrazolyl substituted by Y.
(28) The acid amide derivative or a salt thereof
according to the above (24) , wherein A is phenyl
substituted by X, or benzodioxolanyl substituted by X; B
is furyl substituted by Y, thienyl substituted by Y, or
pyrazolyl substituted by Y; X is halogen, alkyl, or
alkoxy; and Y is halogen, alkyl, or haloalkyl.
(29) The acid amide derivative or a salt thereof
according to the above (24), wherein A is phenyl
substituted by X, or benzodioxolanyl substituted by X; B
is furyl substituted by Y, thienyl substituted by Y, or
pyrazolyl substituted by Y; each of R1 and R2 is alkyl; X
is halogen, alkyl, or alkoxy; and Y is halogen, alkyl, or
haloalkyl.
(30) The acid amide derivative or a salt thereof
according to any one of the above (24) to (29), wherein B
is furyl substituted by Y.
(31) The acid amide derivative or a salt thereof
according to any one of the above (24) to (29), wherein B
is thienyl substituted by Y.
(32) The acid amide derivative or a salt thereof

according to any one of the above (24) to (29), wherein B
is pyrazolyl substituted by Y.
.(33) A fungicidal composition containing the acid
amide derivative or a salt thereof as defined in any one
of the above (1) to (32) as an active ingredient.
(34) A mixed fungicidal composition containing the
acid amide derivative or a salt thereof as defined in any
one of the above (1) to (32), and another fungicidally
active ingredient compound, as active ingredients.
(35) The mixed fungicidal composition according to
the above (34), wherein said another fungicidally active
ingredient compound is at least one member selected from
the group consisting of an anilinopyrimidine compound, a
pyridinamine compound, an azole compound, a quinoxaline
compound, a dithiocarbamate compound, an organic chlorine
compound, an imidazole compound, a cyano acetamide
compound, a phenylamide compound, a sulfenic acid
compound, a copper compound, an isoxazole compound, an
organic phosphorus compound, an N-halogenothioalkyl
compound, a dicarboxyimide compound, a benzanilide
compound, an anilide compound, a piperazine compound, a
pyridine compound, a carbinol compound, a piperidine
compound, a morpholine compound, an organic tin compound,
an urea compound, a cinnamic acid compound, a
phenylcarbamate compound, a cyanopyrrole compound, a
strobilurin compound, an oxazolidinone compound, a
thiazolecarboxamide compound, a silylamide compound, an

amino acid amide carbamate compound, an imidazolidine
compound, a hydroxyanilide compound, a benzenesulfonamide
compound, an oxime ether compound, a phenoxyamide .
compound, an antibiotic, a guanidine compound,
isoprothiolane, pyroquilon, diclomezine, quinoxyfen,
propamocarb hydrochloride, spiroxamine, chloropicrin,
dazomet, metam-sodium, nicobifen, metrafenone, MTF-753,
UBF-307, diclocymet, proquinazid, NC-224, KIF-7767 and
Syngenta 446510 .
(36) The mixed fungicidal composition according to
the above (35), wherein said another fungicidally active
ingredient compound is at least one member selected from
the group consisting of a pyridinamine compound, an azole
compound, a dithiocarbamate compound, an organic chlorine
compound, an imidazole compound, a copper compound, a
dicarboxyimide compound, an anilide compound, a
piperazine compound, a pyridine compound, a carbinol
compound, a phenylcarbamate compound, a cyanopyrrole
compound, a strobilurin compound, a hydroxyanilide
compound, MTF-753, and KIF-7767.
(37) The mixed fungicidal composition according to
the above (36), wherein said another fungicidally active
ingredient compound is at least one member selected from
the group consisting of Fluazinam, Triadimefon,
Bitertanol, Triflumizole, Etaconazole, Propiconazole,
Penconazole, Flusilazole, Myclobutanil, Cyproconazole,
Terbuconazole, Hexaconazole, Furconazole-cis, Prochloraz,

Metconazole, Epoxiconazole, Tetraconazole, Oxpoconazole
fumarate, Sipconazole, Prothioconazole, Triadimenol,
Flutriafol, Difenoconazole, Fluquinconazole,
Fenbuconazole, Bromuconazole, Diniconazole, tricyclazole,
probenazole, Simeconazole, Pefurazoate, Ipconazole,
Imibenconazole, Maneb, Zineb, Mancozeb, Polycarbamate,
Metiram, Propineb, Fthalide, Chlorothalonil, Quintozene,
Benomyl, Thiophanate-Methyl, Carbendazim, Cyazofamid,
Cupric hydroxide, Oxine Copper, Procymidone, Iprodione,
Vinclozolin, Boscalid, Diethofencarb, Fludioxonil,
Fenpiclonil, Azoxystrobin, Kresoxim-Methyl, Metominofen,
Trifloxystrobin, Picoxystrobin, Oryzastrobin,
Dimoxystrobin, Pyraclostrobin, Fluoxastrobin,
Fluacrypyrin, Fenhexamid, Polyoxins, Iminoctadine, MTF-
753, and KIF-7767.
(38) A method for controlling noxious fungi, which
comprises applying an effective amount of the acid amide
derivative or a salt thereof as defined in any one of the
above (1) to (32) .
(3 9) A method for controlling plant diseases, which
comprises applying an effective amount of the acid amide
derivative or a salt thereof as defined in any one of the
above (1) to (32) .
(40) A method for protecting crop plants, which
comprises applying an effective amount of the acid amide
derivative or a salt thereof as, defined in any one of the
above (1) to (32) .

(41) A method for improving crop yields, which
comprises applying an effective amount of the acid amide
derivative or a salt thereof as defined in any one of the
above (1) to (32).
Now, the present invention will be described in
further detail with reference to Examples. However, it
should be understood that the present invention is by no
means restricted thereto. Firstly, Preparation Examples
for the acid amide derivative of the formula (I) , (I-α)
or a salt thereof will be described.
PREPARATION EXAMPLE 1
Preparation of N-[(3',4'-dichloro-1,1-dimethyl)phenacyl]-
2-methyl-3-furancarboxamide (after-mentioned compound
No.1-57)
(1) A mixture comprising 10.0 g of 3,4-
dichlorobenzoyl chloride, 9.31 g of ethyl 2-
bromoisobutyrate and 9 0 ml of anhydrous diethyl ether,
was dropwise added to 3.12 g of zinc in a nitrogen
atmosphere, followed by a reaction for 15 hours under
reflux. The reaction mixture was filtered through
celite, and the filtrate was washed with 2 0% sulfuric
acid and then with water. The organic layer was dried
over anhydrous magnesium sulfate and then concentrated
under reduced pressure. The residue was purified by
silica gel column chromatography (developing solvent:
ethyl acetate/n-hexane=l/19) to obtain 8.7 g of oily
ethyl 2-(3',4'-dichlorobenzoyl)isobutyrate. The NMR

spectrum data of this product is as follows.
1H-NMR δppm (Solvent : CDCl3/400 MHz)
1.11(t,3H),1.52(s,6H),4.14(q,2H),7.48(d,lH),7.63(dd,
1H),7.96(d,lH)
(2) A mixture comprising 8.7 g of ethyl 2-(3',4'-
dichlorobenzoyl)isobutyrate, 14.2 ml of sulfuric acid,
14.2 ml of water and 40 ml of acetic acid, was reacted
for 15 hours under reflux. The reaction mixture was put
into ice water and extracted with ethyl acetate, followed
by washing with water. The organic layer was dried over
anhydrous magnesium sulfate and then concentrated under
reduced pressure. The residue was purified by silica gel
column chromatography (developing solvent: ethyl
acetate/n-hexane=l/19) to obtain 6.47 g of oily 3,4-
dichloroisobutyrophenone. The NMR spectrum data of this
product is as follows.
1H-NMR δppm (Solvent: CDCl3/4 0 0 MHz)
1.21(d,6H),3.46(m,lH),7.55(d,1H),7.79(dd,lH),8.02(d,
1H)
(3) 9.32g of phenyltrimethylammonium tribromide was
added to a mixture comprising 6.47 g of 3,4-
dichloroisobutyrophenone and 100 ml of tetrahydrofuran,
followed by a reaction for 4 hours at room temperature.
The reaction mixture was filtered, and the filtrate was
concentrated under reduced pressure to obtain 6.39 g of
oily α-bromo-3 , 4-dichloroisobutyrophenone. The NMR
spectrum data of this product is as follows.

1H-NMR δppm (Solvent : CDCl3/30 0 MHz)
2.01(s,6H),7.50(d,lH),8.0(dd,1H),8.20(d,lH)
(4) 2.8 g of. sodium azide was added to a mixture
comprising 6.39 g of α-bromo-3,4-dichloroisobutyrophenone
and 60 ml dimethyl sulfoxide, followed by a reaction for
one hour at 50°C. The reaction mixture was put into
water and extracted with ethyl acetate, followed by
washing with water. The organic layer was dried over
anhydrous magnesium sulfate and then concentrated under
reduced pressure. The residue was purified by silica gel
column chromatography (developing solvent: ethyl
acetate/n-hexane=l/9) to obtain 6.34 g of oily α-azide-
3 ,4-dichloroisobutyrophenone. The NMR spectrum data of
this product is as follows.
1H-NMR δppm (Solvent: CDCl3/300 MHz)
1.60(s,6H),7.53(d,lH),7.97(dd,lH],8.20(d,lH)
(5) 7.74 g of triphenylphosphine was added to a
mixture comprising 6.34 g of α-azide-3,4-
dichloroisobutyrophenone, 90 ml of tetrahydrofuran and
3.2 ml of water, followed by a reaction for 23 hours at
room temperature. The reaction mixture was concentrated
under reduced pressure. To the residue, water and then
hydrochloric acid were added to bring it to be weakly
acidic, followed by washing with diethyl ether. The
aqueous layer was neutralized with an aqueous sodium
hydroxide solution and extracted with diethyl ether. The
organic layer was dried over anhydrous magnesium sulfate

and concentrated under reduced pressure. To the residue,
ethyl acetate was added, and hydrogen chloride gas was
introduced under cooling with ice. Formed solid was
collected by filtration and dried to obtain 5.92 g of α-
amino-3,4-dichloroisobutyrophenone hydrochloride.
(6) 0.31 g of triethylamine was added to a mixture
comprising 0.3 g of α-amino-3, 4-dichloroisobutyrophenone
hydrochloride and 10 ml of tetrahydrofuran, followed by
stirring for 5 hours at room temperature. The mixture
was concentrated under reduced pressure. To a mixture
comprising the obtained residue, 0.195 g of 2-methyl-3-
furancarboxylic acid and 2 0 ml of dichloromethane, a
mixture comprising 0.29 g of M,N'-
dicyclohexylcarbodiimide and 10 ml of dichloromethane,
was dropwise added under cooling with ice, followed by a
reaction for 15 hours at room temperature. The reaction
mixture was filtered, and the filtrate was diluted with
dichloromethane, and washed with an aqueous potassium
carbonate solution and then with water. The organic
layer was dried over anhydrous sodium sulfate and then
concentrated under reduced pressure. The residue was
purified by silica gel column chromatography (developing
solvent: ethyl acetate/n-hexane=1/9) to obtain 0.08 g of
the desired product having a melting point of from 175 to
178°C. The NMR spectrum data of this product is as
follows.
1H-NMR δppm (Solvent: CDCl3/400 MHz)

1.71(s,6H),2.43(s,3H),6.28(s,1H),6.44(d,1H),7.26(d,l
H),7.44(d,1H),7.84(dd,1H), 8.11(d,1H)
PREPARATION EXAMPLE 2
Preparation of N-[(3'-difluoromethoxy-1,1-
dimethyl)phenacyl]-5-chloro-l,3-dimethyl-4-pyrazole
carboxamide (after-mentioned compound No. 1-72)
(1) A Grignard reagent prepared by using 0.75 g of
magnesium, 4.46 g of 2-bromopropane and 24 ml of
anhydrous diethyl ether, was dropwise added to a mixture
comprising 4.09 g of 3-difluoromethoxybenzonitrile and 20
ml of anhydrous diethyl ether. After completion of the
dropwise addition, the mixture was reacted at room
temperature for 27 hours. The reaction mixture was put
into ice water, and 6N sulfuric acid was added to bring
the mixture to be weakly acidic, followed by stirring for
0.5 hour. The mixture was extracted with diethyl ether
and washed with water. The organic layer was dried over
anhydrous magnesium sulfate and then concentrated under
reduced pressure. The residue was purified by silica gel
column chromatography (developing solvent: ethyl
acetate/n-hexane=l/19), to obtain 2.04 g of 3-
difluoromethoxyisobutyrophenone. The NMR spectrum data
of this product is as follows.
1H-NMR δppm (Solvent: CDCl3/300 MHz)
1.23(d,6H),3.52(m,1H),6.56(t,1H),7.32(dd,1H),7.48(t,
1H),7.70(s,1H),7.80(d,1H)
(2) 3.58 g of phenyltrimethylammonium tribromide was

added to a mixture comprising 2.04 g of 3-
difluoromethoxyisobutyrophenone and 30 ml of
tetrahydrofuran, followed by a reaction for two hours, at
room temperature. The reaction mixture was filtered, and
the filtrate was concentrated under reduced pressure to
obtain 2.79 g of oily a-bromo-3-
difluoromethoxyisobutyrophenone.
(3) 1.24 g of sodium azide was added to a mixture
comprising 2.79 g of a-bromo-3-
difluoromethoxyisobutyrophenone and 35 ml of dimethyl
sulfoxide, followed by a reaction for one hour at 50°C.
The reaction mixture was put into water and extracted
with ethyl acetate, followed by washing with water. The
organic layer was dried over anhydrous magnesium sulfate
and then concentrated under reduced pressure. The
residue was purified with silica gel column
chromatography (developing solvent: ethyl acetate/n-
hexane=l/9) to obtain 2.21 g of oily α-azide-3-
difluoromethoxyisobutyrophenone. The WMR spectrum data
of this product is as follows.
1H-NMR δppm (Solvent: CDCl3 /300 MHz)
1.61(s,6H),6.56(t,1H),7.34(dd,1H),7.48(t,1H),7.86(s,
1H),7.98(d,1H)
(4) A mixture comprising 2.18 g of α-azide-3-
difluoromethoxyisobutyrophenone, 35 ml of methanol and
0.109 g of 5% palladium carbon, was reacted for 1.5 hours
at room temperature in a hydrogen atmosphere. The

reaction mixture was filtered through celite, and the
filtrate was concentrated under reduced pressure. To the
residue, ethyl acetate was added, and hydrogen chloride
gas was introduced under cooling with ice, followed by
concentration under reduced pressure to obtain 1.7 6 g of
a-amino-3-difluoromethoxyisobutyrophenone hydrochloride.
(5) 0.33 g of triethylamine was added to a mixture
comprising 0.3 g of a-amino-3-
difluoromethoxyisobutyrophenone hydrochloride and 10 ml
of tetrahydrofuran, and a mixture comprising 0.25 g of 5-
chloro-1,3-dimethyl-4-pyrazolecarbonyl chloride and 5 ml
of tetrahydrofuran, was dropwise added thereto under
cooling with ice. After completion of the dropwise
addition, the mixture was reacted at room temperature for
3 hours. The reaction mixture was extracted with ethyl
acetate, followed by washing with water. The organic
layer was dried over anhydrous magnesium sulfate and then
concentrated under reduced pressure. The residue was
purified by silica gel column chromatography (developing
solvent: ethyl acetate/n-hexane=l/4) to obtain 0.23 g of
the desired product having a melting point of from 13 8 to
139°C. The NMR spectrum data of this product is as
follows.
1H-NMR δppm (Solvent: CDCl3/400 MHz)
1.75(s,6H),2.28(s,3H),3.80(s,3H),6.50(t,1H),6.80(s,l
H),7.23(dd,1H),7.38(t,1H),7.84(s,1H),7.86(d,1H)
PREPARATION EXAMPLE 3

Preparation of N-[2-(2'-naphthylcarbonyl)-2-propyl]-5-
chloro-1,3-dimethyl-4-pyrazolecarboxamide (compound No.
2-1).
(1) A Grignard reagent prepared by using 0.61 g of
magnesium, 3.6 g of 2-bromopropane and 18 ml of anhydrous
diethyl ether, was dropwise added to a mixture comprising
3.0 g of 2-naphthonitrile and 20 ml of anhydrous diethyl
ether. After completion of the dropwise addition, the
mixture was reacted for 12 hours under reflux. The
reaction mixture was put into ice water, and 6N sulfuric
acid was added to bring the mixture to be weakly acidic,
followed by stirring for 0.5 hour. The mixture was
extracted with ethyl acetate, followed by washing with
water. The organic layer was dried over anhydrous
magnesium sulfate, and then concentrated under reduced
pressure. The residue was purified by silica gel column
chromatography (developing solvent: ethyl acetate/n-
hexane=l/50) to obtain 1.14 g of 2-naphthyl isopropyl
ketone. The NMR spectrum data of this product is as
follows.
1H-NMR δppm (Solvent: CDCl3/400 MHz)
1.27(d,6H),3.73(m,1H),7.53 to 7.65(m,2H), 7.86 to
7.92(m,2H),7.97(d,1H),8.03(dd,1H),8.48(d,1H)
(2) 2.16 g of phenyltrimethylammonium tribromide was
added to a mixture comprising 1.14 g of 2-naphthyl
isopropyl ketone and 25 ml of tetrahydrofuran, and the
mixture was reacted at room temperature for 3 hours. The

reaction mixture was filtered, and the filtrate was
concentrated under reduced pressure to obtain 1.59 g of
oily α-bromoisopropyl 2-naphthyl ketone.
(3) 0.75 g of sodium azide was added to a mixture
comprising 1.59 g of a-bromoisopropyl 2-naphthyl ketone
and 40 ml of dimethyl sulfoxide, and the mixture was
reacted at 50°C for 1.5 hours. The reaction mixture was
put into water and extracted with ethyl acetate, followed
by washing with water. The organic layer was dried over
anhydrous magnesium sulfate and then concentrated under
reduced pressure. The residue was purified by silica gel
column chromatography (developing solvent: ethyl
acetate/n-hexane=1/9) to obtain 1.19 g of oily Di-
az ide is opropyl 2-naphthyl ketone.
The NMR spectrum data of this product is as follows.
1H-NMR δppm (Solvent: CDCl3/400 MHz)
1.68(S,1H),7.54 to 7.66(m,2H),7.86 to
7.90(m,2H),7.98(d,1H),8.10(dd,1H),8.74(d,1H)
(4) A mixture comprising 0.3 g of α-azideisopropyl
2-naphthyl ketone, 10 ml of methanol and 15 mg of 5%
palladium carbon, was reacted for one hour at room
temperature in a hydrogen atmosphere. The reaction
mixture was filtered through celite, and the filtrate was
concentrated under reduced pressure to obtain 0.26 g of
oily a-aminoisopropyl 2-naphthyl ketone
(5) 0.19 g of triethylamine was added to a mixture
comprising 0.26 g of a-aminoisopropyl 2-naphthyl ketone

and 10 ml of tetrahydrofuran, and a mixture comprising
0.24 g of 5-chloro-1,3-dimethyl-4-pyrazolecarbonyl
chloride and 5 ml of tetrahydrofuran, was dropwise added
thereto under cooling with ice. After the dropwise
addition, the mixture was reacted for 15 hours at room
temperature. The reaction mixture was extracted with
ethyl acetate, followed by washing with water. The
organic layer was dried over anhydrous magnesium sulfate
and then concentrated under reduced pressure. The
residue was purified by silica gel column chromatography
(developing solvent: ethyl acetate/n-hexane=2/3) to
obtain 0.15 g of the desired product having a melting
point of from 145 to 147°C. The NMR spectrum data of
this product is as follows.
1H-NMR δppm (Solvent: CDCl3/300 MHz)
1.87(s,6H),2.28(s,3H),3.79(s,3H),7.05(s,1H),7.48 to
7.58(m,2H),7.80 to 7.90(m,3H),8.05(dd,1H),8.56(d,1H)
PREPARATION EXAMPLE 4
Preparation of N-[2-[ (2',2',3',3'-tetrafluoro-1' , 4 ' -
benzodioxan-6'-yl)carbonyl]isopropyl]-3-methyl-2-
thiophene carboxamide (after-mentioned compound No.4-10)
(1) 7.3 ml of n-butyllithium (1.57M n-hexane
solution) was dropwise added at -50°C in a nitrogen
atmosphere to a mixture comprising 3.0 g of 6-brontio-
2,2,3,3-tetrafluoro-1,4-benzodioxane and 38 ml of diethyl
ether, followed by stirring for 30 minutes at the same
temperature. Then, 0.83 g of isobutylaldehyde was

dropwise added at a temperature of at most -70°C, and the
mixture was heated to room temperature and reacted for 15
hours. . The reaction mixture was put into water and
adjusted to be weakly acidic with hydrochloric acid, and
extracted with diethyl ether. The organic layer was
washed with water, dried over magnesium sulfate and then
concentrated under reduced pressure. The residue was
purified by silica gel column chromatography (developing
solvent: ethyl acetate/n-hexane=l/9) to obtain 1.8 g of
oily 1-(2',2',3',3'-tetrafluoro-1',4'-benzodioxan-6'-yl)-
2-methylpropanol. The NMR spectrum data of this product
is as follows.
1H-NMR δppm (Solvent: CDCl3/400 MHz)
0.83(d,3H),0.9 6(d,3H),1.92(m,1H),4.40(d,1H),6.90(d,l
H),7.10(s,2H),7.14(s,1H)
(2) A mixture comprising 1.8 g of 1- (2 ' ,2 ' ,3 ' ,3 ' -
tetrafluoro-1',4'-benzodioxan-6'-yl)-2-methylpropanol and
7 ml of dichloromethane, was added to a mixture
comprising 2.08 g of pyridinium chlorochromate, 1.05 g of
sodium acetate and 2 0 ml of dichloromethane, followed by
a reaction for two hours at room temperature. The
reaction mixture was filtered through celite, and the
filtrate was concentrated under reduced pressure. The
residue was purified by silica gel column chromatography
(developing solvent: ethyl acetate/n-hexane=l/19) to
obtain 1.40 g of oily 2,2,3,3-tetrafluoro-1,4-
benzodioxan-6-yl isopropyl ketone. The NMR spectrum data

of this product is as follows.
1H-NMR δppm (Solvent: CDCl3/400 MHz)
1.23(d,6H),3.48(m,1H),7.24(d,1H),7.78(d,1H),7.81(dd,
1H)
(3) 1.89 g of phenyltrimethylammonium tribromide was
added to a mixture comprising 1.40 g of 2,2,3,3-
tetrafluoro-1,4-benzodioxan-6-yl isopropyl ketone and
19.7 ml of tetrahydrofuran, followed by a reaction for
two hours at room temperature. The reaction mixture was
filtered, and the filtrate was concentrated under reduced
pressure to obtain 1.78 g of oily a-bromoisopropyl
2,2,3,3-tetrafluoro-1,4-benzodioxan-6-yl ketone.
(4) 0.65 g of sodium azide was added to a mixture
comprising 1.78 g of a-bromoisopropyl 2,2,3,3-
tetrafluoro-1,4-benzodioxan-6-yl ketone and 10 ml of
dimethyl sulfoxide, followed by a reaction for two hours
at 50°C. The reaction mixture was put into water, and
extracted with diethyl ether, followed by washing with
water. The organic layer was dried over anhydrous
magnesium sulfate and then concentrated under reduced
pressure. The residue was purified by silica gel column
chromatography (developing solvent: ethyl acetate/n-
hexane=1/19) to obtain 1.5 g of oily cx-azideisopropyl
2,2,3,3-tetrafluoro-1,4-benzodioxan-6-yl ketone. The NMR
spectrum data of this product is as follows.
1H-NMR δppm (Solvent: CDCl3/400 MHz)
1.61(s,6H),7.23(d,1H),8.01 to 8.03(m,2H)

(5) A mixture comprising 0.2 5 g of α-azideisopropyl
2,2,3,3-tetrafluoro-1,4-benzodioxan-6-yl ketone, 15 ml of
methanol and 13 mg of 5% palladium carbon, was reacted
for one hour at room temperature in a hydrogen
atmosphere. The reaction mixture was filtered through
celite, and the filtrate was concentrated under reduced
pressure to obtain 0.23 g of oily ot-aminoisopropyl
2,2,3,3-tetrafluoro-1,4-benzodioxan-6-yl ketone.
(6) 0.16 g of triethylamine was added to a mixture
comprising 0.23 g of α-aminoisopropyl 2,2,3,3-
tetrafluoro-1,4-benzodioxan-6-yl ketone and 10 ml of
tetrahydrofuran, and a mixture comprising 0.13 g of 3-
methyl-2-thiophene carbonyl chloride and 5 ml of
tetrahydrofuran, was dropwise added thereto under cooling
with ice, followed by a reaction for 3 hours at room
temperature. The reaction mixture was extracted with
ethyl acetate, followed by washing with water. The
organic layer was dried over anhydrous magnesium sulfate
and then concentrated under reduced pressure. The
residue was purified by silica gel column chromatography
(developing solvent: ethyl acetate/n-hexane=l/4) to
obtain 0.23 g of the desired product having a melting
point of from 12 0 to 122°C. The NMR spectrum data of
this product is as follows.
1H-NMR δppm (Solvent: CDCl3/30 0 MHz)
1.76(s,6H),2.39(s,3H),6.54(s,1H),6.84(d,1H),7.24(d,l
H),7.42(d,1H),7.84(s,1H),7.96(s,1H)

PREPARATION EXAMPLE 5
Preparation of N-[(3',4'-dichloro-1,1-dimethyl)phenacyl]-
3-methyl-2-thiophene carboxamide (after-mentioned
compound No.1-20)
3 03 mg of triethylamine was added to a mixture
comprising 268 mg of α-amino-3,4-dichloroisobutyrophenone
hydrochloride obtained in accordance with the process of
(1) to (5) in the above Preparation Example 1 and 5 ml of
tetrahydrofuran, and a mixture comprising 265 mg of 3-
methyl-2-thiophene carbonyl chloride and 2.5 ml of
tetrahydrofuran, was dropwise added thereto under cooling
with ice. After completion of the dropwise addition, the
mixture was reacted for 3 hours at room temperature. The
reaction mixture was extracted with ethyl acetate,
followed by washing with water. The organic layer was
dried over anhydrous magnesium sulfate and then
concentrated under reduced pressure. The residue was
purified by silica gel column chromatography (developing
solvent: ethyl acetate/n-hexane=1/3) to obtain 180 mg of
the desired product having a melting point of 141°C. The
NMR spectrum data of this product is as follows.
1H-NMR δppm (Solvent: CDCl3/400 MHz)
1.72(s,6H),2.37(s,3H),6.53(s,1H),6.85(d,1H),7.25(d,l
H) ,7.43(d,1H),7.86(dd,1H),8.13(s,1H)
PREPARATION EXAMPLE 6
Preparation of N-[(4'-methoxy-2'-methyl-1,1-
dimethyl)phenacyl]-3-methyl-2-thiophene carboxamide

(after-mentioned compound No.1-160)
(1) A mixture comprising 5.7 g of isobutylyl
chloride and 5 ml of carbon disulfide, was dropwise added
at most 10°C to a mixture comprising 7.15 g of aluminum
chloride and 20 ml of carbon disulfide, followed by a
reaction for 0.5 hour. Then, a mixture comprising 5.0 g
of m-cresol and 5 ml of carbon disulfide was dropwise
added at most 5°C, followed by a reaction for 4 hours at
room temperature. The reaction mixture was put into a
mixture of ice water and hydrochloric acid and extracted
with methylene chloride, followed by washing with water.
The organic layer was dried over anhydrous sodium sulfate
and then concentrated under reduced pressure. To the
residue, 60 ml of tetrahydrofuran, 3 0 ml of water and 3.7
g of sodium hydroxide, were added, followed by a reaction
for 1.5 hours at room temperature. The reaction mixture
was concentrated under reduced pressure, then put into
ice water and adjusted to be weakly acidic with dilute
sulfuric acid, and then extracted with ethyl acetate.
The organic layer was dried over anhydrous magnesium
sulfate and then concentrated under reduced pressure.
The residue was purified by silica gel column
chromatography (developing solvent: ethyl acetate/n-
hexane=l/9) to obtain 2.45 g of solid 4-hydroxy-2-methyl-
isobutyrophenone. The NMR spectrum data of this product
is as follows.
1H-NMR δppm (Solvent: CDCl3/400 MHz)

1.15(d,6H),2.43(s,3H),3.40(m,1H),6.70(m,2H),7.57(d,l
H)
(2). A mixture comprising 0 . 62. g of dimethyl sulfate
and 3 ml of dimethylformamide, was added to a mixture
comprising 0.8 g of 4-hydroxy-2-methyl-isobutyrophenone,
0.68 g of potassium carbonate and 15 ml of
dimethylformamide, followed by a reaction for 3 hours at
room temperature. The reaction mixture was put into
water and extracted with ethyl acetate, followed by
washing with water. The organic layer was dried over
anhydrous magnesium sulfate and then concentrated under
reduced pressure. The residue was purified by silica gel
column chromatography (developing solvent: ethyl
acetate/n-hexane=l/9) to obtain 0.59 g of oily 4-methoxy-
2-methylisobutyrophenone. The NMR spectrum data of this
product is as follows.
1H-NMR δppm (Solvent: CDCl3/400 MHz)
1.13(d,6H),2.46(s,1H),3.38(m,1H),6.72(m,2H),7.59(d,1
H)
(3) 1.16 g of phenyltrimethyl ammonium tribromide
was added to a mixture comprising 0.59 g of 4-methoxy-2-
methylisobutyrophenone and 15 ml of tetrahydrofuran,
followed by a reaction for 2.5 hours at room temperature.
Diethyl ether was added to the reaction mixture, and the
insoluble matter was filtered off. The filtrate was
concentrated under reduced pressure to obtain 0.7 g of
oily α-bromo-4-methoxy-2-methylisobutyrophenone.

(4) 0.4 g of sodium azide was added to a mixture
comprising 0.7 g of α-bromo-4-methoxy-2-
methylisobutyrophenone and -8 ml of dimethyl sulfoxide,
followed by a reaction for 1.5 hours at 50°C. The
reaction mixture was put into water and extracted with
ethyl acetate, followed by washing with water. The
organic layer was dried over anhydrous magnesium sulfate
and then concentrated under reduced pressure. The
residue was purified by silica gel column chromatography
(developing solvent: ethyl acetate/n-hexane=l/9) to
obtain 0.67 g of oily α-azide-4-methoxy-2-
methylisobutyrophenone. The NMR spectrum data of this
product is as follows.
1H-NMR δppm (Solvent: CDCl3/300 MHz)
1.54(s,6H),2.33(s,1H),3.81(s,3H),6.72(dd,1H),6.75(d,
1H),7.61(d,1H)
(5) A mixture comprising 0.25 g of cx-azide-4-
methoxy-2-methylisobutyrophenone, 10 ml of methanol and
13 mg of 5% palladium carbon, was reacted for 3 hours at
room temperature in a hydrogen atmosphere. The reaction
mixture was filtered through celite, and the filtrate was
concentrated under reduced pressure to obtain 0.23 g of
oily a-amino-4-methoxy-2-methylisobutyrophenone.
(6) 0.13 g of triethylamine was added to a mixture
comprising 0.22 g of α-amino-4-methoxy-2-
methylisobutyrophenone and 12 ml of tetrahydrofuran, and
a mixture comprising 0.17 g of 3-methyl-2-thiophene

carbonyl chloride and 3 ml of tetrahydrofuran, was
dropwise added thereto under cooling with ice. After
completion of the dropwise addition, the mixture was
reacted at room temperature for two hours. The reaction
mixture was extracted with ethyl acetate, followed by
washing with water. The organic layer was dried over
anhydrous magnesium sulfate and then concentrated under
reduced pressure. The residue was purified by silica gel
column chromatography (developing solvent: ethyl
acetate/n-hexane=1/3) to obtain 0.35 g of the desired
product having a melting point of from 99 to 101°C. The
NMR spectrum data of this product is as follows.
1H-NMR δppm (Solvent: CDCl3/300 MHz)
1.77(s,6H),2.38(s,3H),2.45(s,3H),6.81(dd,1H),6.71(s,
1H),6.85(m,2H),7.26(d,1H),7.49(d,1H)
PREPARATION EXAMPLE 7
Preparation of N-[(3',4'-dimethoxy-1,1-
dimethyDphenacyl] -3-methyl-2-thiophene carboxamide
(after-mentioned compound No.1-53 5)
(1) An isopropyl magnesium bromide ether solution
prepared by using 5.6 g of 2-bromopropane, 0.94 g of
magnesium and 30 ml of diethyl ether, was dropwise added
to a mixture comprising 5.0 g of 3,4-
dimethoxybenzaldehyde and 50 ml of diethyl ether,
followed by a reaction for 15 hours under reflux. The
reaction mixture was put into ice water, and dilute
sulfuric acid was added, followed by stirring. Then, the

mixture was extracted with methylene chloride, followed
by washing with water. The organic layer was dried over
anhydrous sodium sulfate and then concentrated under
reduced pressure to obtain 6.3 g of oily l-(3',4'-
dimethoxyphenyl)-2-methylpropanol.
(2) A mixture comprising 6.28 g of l-(3',4'-
dimethoxyphenyl)-2-methylpropanol and 30 ml of
dichloromethane, was added to a mixture comprising 6.5 g
of pyridinium chlorochromate, 4.9 g of sodium acetate and
100 ml of dichloromethane, followed by a reaction for 15
hours at room temperature. The reaction mixture was
filtered through celite, and the filtrate was
concentrated under reduced pressure. The residue was
purified by silica gel column chromatography (developing
solvent: ethyl acetate/n-hexane=3/7) to obtain 3.9 g of
oily 3,4-dimethoxyisobutyrophenone. The NMR spectrum
data of this product is as follows.
1H-DMR δppm (Solvent: CDCl3/400 MHz)
1.70(d,6H),3.50(m,1H),3.89(s,3H),3.90(s,3H),6.85(d,l
H),7.50(d,1H),7.56(dd,1H)
(3) 1.81 g of phenyltrimethyl ammonium tribromide
was added to a mixture comprising 1.0 g of 3,4-
dimethoxyisobutyrophenone and 2 0 ml of tetrahydrofuran,
followed by a reaction for two hours at room temperature.
To the reaction mixture, diethyl ether was added, and the
insoluble matter was filtered off. The filtrate was
concentrated under reduced pressure to obtain oily a-

bromo-3,4-dimethoxyisobutyrophenone.
(4) 0.62 g of sodium azide was added to a mixture
comprising α-bromo-3,4-dimethoxyisobutyrophenone and 20
ml of dimethyl sulfoxide, followed by a reaction for 1.5
hours at 50°C. The reaction mixture was put into water
and extracted with ethyl acetate, followed by washing
with water. The organic layer was dried over anhydrous
magnesium sulfate and then concentrated under reduced
pressure. The residue was purified by silica gel column
chromatography (developing solvent: ethyl acetate/n-
hexane=l/4) to obtain 1.1 g of oily α-azide-3,4-
dimethoxyisobutyrophenone. The NMR spectrum data of this
product is as follows.
1H-NMR δppm (Solvent: CDCl3/4 00 MHz)
1.56(s,6H),3.91(s,3H),3.93(s,3H),6.86(d,1H),7.62(d,l
H),7.94(dd,1H)
(5) A mixture comprising 0.25 g of α-azide-3,4-
dimethoxyisobutyrophenone, 15 ml of methanol and 13 mg of
5% palladium carbon, was reacted for 3 hours at room
temperature in a hydrogen atmosphere. The reaction
mixture was filtered through celite, and the filtrate was
concentrated under reduced pressure to obtain 0.2 g of
oily a-amino-3,4-dimethoxyisobutyrophenone.
(6) 0.11 g of triethylamine was added to a mixture
comprising 0.2 g of a-amino-3,4-dimethoxyisobutyrophenone
and 12 ml of 1,2-dichloroethane, and a mixture comprising
0.14 g of 3-methyl-2-thiophenecarbonylchloride and 2 ml

of 1,2-dichloroethane, was dropwise added thereto under
cooling with ice. After completion of the dropwise
addition, the mixture was reacted for 1.5 hours at room
temperature. The reaction mixture was extracted with
methylene chloride, followed by washing with water. The
organic layer was dried over anhydrous sodium sulfate and
then concentrated under reduced pressure. The residue
was purified by silica gel column chromatography
(developing solvent: ethyl acetate/n—hexane=3/2) to
obtain 0.1 g of the desired product having a melting
point of from 13 8 to 140°C. The NMR spectrum data of
this product is as follows.
1H-NMR δppm (Solvent: CDCl3/3 00 MHz)
1.82(s,6H),2.44(s,3H),3.89(s,6H),6.80(d,1H),6.85(d,l
H),6.88(s,1H),7.23(d,1H),7.63(d,1H),7.75(dd,1H)
Now, typical examples of the acid amide derivative
of the formula (I), (I-α) or a salt thereof will be given
in Tables 1 to 9. These compounds can be prepared in
accordance with the above Preparation Examples or by the
above-described various processes.
In the Tables, No. represents compound No., Me
methyl, Et ethyl, Pr(i) isopropyl, P(n) n-propyl, Bu(t)
tert-butyl, Bu(n) n-butyl, Bu(sec) sec-butyl, CO
carbonyl, CO2 carboxyl, and Ph phenyl. Further, in the
Tables, Ph (4-C1) represents phenyl having a chlorine
atom substituted at the 4-position, and Ph(3,4-Cl2)
represents a phenyl having chlorine atoms substituted at

the 3- and 4-positions. The same applies to other
expressions. Further, abbreviations D1 to D7 and B1 to
B117 used in the Tables represent the following
substituents, respectively.





































































Now, Test Examples for the composition of the
present invention will be described. In each test, the
controlling index was determined on the basis of the
following standards:
[Controlling index]:[Degree of disease outbreak:Visual
observation]
5 : No lesions nor sporulation recognizable
4 : Area of lesions, length of lesions, number of
lesions or area of sporulation is less than 10% of non-
treated plot
3 : Area of lesions, length of lesions, number of
lesions or area of sporulation is less than 40% of non-
treated plot
2 : Area of lesions, length of lesions, number of
lesions or area of sporulation is less than 7 0% of non-
treated plot
1 : Area of lesions, length of lesions, number of
lesions or area of sporulation is at least 70% of non-
treated plot
TEST EXAMPLE 1: Test on Preventive Effect Against Wheat
Powdery Mildew
Wheat (cultivar: Norin-61-go) was cultivated in a
plastic pot having a diameter of 7.5 cm, and when it
reached 1.5-leaf stage, 10 ml of a chemical solution
having the acid amide derivative of the formula (I) or a
salt thereof adjusted to a prescribed concentration, was
applied by a spray gun. After the chemical solution

dried (the same day as the application), conidia of
Erysiphe graminis were dusted and inoculated and
maintained in a constant temperature chamber at 20oC.
From 6 to 7 days after the inoculation, the area of
sporulation was investigated, and the controlling index
was determined in accordance with the above evaluation
standards. The test was carried out with respect to the
above compounds No. 1-13, 1-29, 1-39, 1-54, 1-90, 1-96,
1-100, 1-101, 1-106, 1-107, 1-109, 1-124, 1-125, 1-127,
1-148, 1-152, 1-156, 1-174, 1-175, 1-190, 1-205, 1-516,
3-4, 3-9, 3-10, 3-12, 3-19, 3-20, 4-19, 6-1 and 7-2, and
all compounds showed effects with a controlling index of
4 or 5 at a concentration of 500 ppm.
TEST EXAMPLE 2: Test on Preventive Effect Against
Cucumber Powdery Mildew
Cucumber (cultivar: Sagamihanpaku) was cultivated in
a plastic pot having a diameter of 7.5 cm, and when it
reached 1.5-leaf stage, 10 ml of a chemical solution
having the acid amide derivative of the formula (I) or a
salt thereof adjusted to a prescribed concentration, was
applied by a spray gun. After the chemical solution
dried (the same day as the application or the next day),
a suspension of conidia of Sphaerotheca fuliginea was
sprayed and inoculated and maintained in a constant
temperature chamber at 2 0°C. From 6 to 7 days after the
inoculation, the area of sporulation was investigated,
and the controlling index was determined in accordance

with the above evaluation standards. The test was
carried out with respect to the above compounds No. 1-6,
1-9, 1-11,-1-14., 1-15, 1-17 to 1-22, 1-27 to 1-29, 1-32,
1-33, 1-36, 1-39, 1-41 to 1-43, 1-47, 1-53 to 1-56, 1-62
to 1-64, 1-66, 1-73, 1-77, 1-79, 1-90, 1-93, 1-97 to 1-
104, 1-106 to 1-108, 1-111, 1-115, 1-119, 1-120, 1-124,
1-127, 1-129, 1-131, 1-148, 1-150, 1-152, 1-156, 1-160,
1-161, 1-164, 1-165, 1-167, 1-170, 1-172, 1-174, 1-175,
1-190, 1-205, 1-516, 2-1, 2-14, 3-2, 3-4, 3-6, 3-9, 3-10,
3-12, 3-19, 3-20, 3-23, 4-10 and 6-1 to 6-3, and all
compounds showed effects with a controlling index of 4 or
5 at a concentration of 500 ppm. The test was carried
out with respect to the above compound No. 1-34, it
showed an effect with a controlling index of 4 at a
concentration of 2 00 ppm.
TEST EXAMPLE 3: Test on Preventive Effect Against Rice
Blast
Rice (cultivar: Nihonbare) was cultivated in a
plastic pot having a diameter of 7.5 cm, and when it
reached 1.5-leaf stage, 10 ml of a chemical solution
having the acid amide derivative of the formula (I) or a
salt thereof adjusted to a prescribed concentration, was
applied by a spray gun. After the chemical solution
dried (the same day as the application or the next day),
a suspension of conidia of Pyricularia oryzae was sprayed
and inoculated and maintained in an inoculation box at
20°C for 24 hours and thereafter maintained in a constant

temperature chamber at 20°C. From 5 to 7 days after the
inoculation, the number of lesions were investigated, and
the controlling index was determined in accordance with
the above evaluation standards. The test was carried out
with respect to the above compounds No. 1-6, 1-9, 1-13,
1-14, 1-28, 1-45, 1-47, 1-52, 1-53, 1-55, 1-56, 1-62, 1-
63, 1-66, 1-75, 1-77, 1-79, 1-109, 1-119, 1-164, 2-1, 2-
2, 3-25 and 4-19, and all compounds showed effects with a
controlling index of 4 or 5 at a concentration of 500
ppm.
TEST EXAMPLE 4: Test on Preventive Effect Against Kidney
Bean Gray Mold
Kidney bean (cultivar: Taisyou Kintoki) was
cultivated in a plastic pot having a diameter of 15 cm,
and when the main leaf developed sufficiently, 10 ml of a
chemical solution having the acid amide derivative of the
formula (I) or a salt thereof adjusted to a prescribed
concentration, was applied by a spray gun. After the
chemical solution dried (the same day as the application
or the next day), a suspension of spores of Botrytis
cinerea (potato-glucose extract diluted to 50% with
water) was inoculated and maintained in a constant
temperature chamber at 20°C. Three days after the
inoculation, the length of lesions (mm) was investigated,
and the controlling index was determined in accordance
with the above evaluation standards. The test was
carried out with respect to the above compounds No. 1-11,

1-15, 1-17, 1-20, 1-22, 1-27, 1-41, 1-43, 1-52, 1-80, 1-
99, 1-102, 1-112 to 1-115, 1-117, 1-118, 1-120, 1-125, 1-
131,- 1-136, 1-160, 1-162, 1-169, 1-172, 1-176, 1-180, 1-
182, 1-186 to 1-189, 1-273, 2-2, 2-9, 2-13, 2-14 and 7-6,
and all compounds showed effects with, a controlling index
of 4 or 5 at a concentration of 500 ppm.
TEST EXAMPLE 5: Test on Preventive Effect Against Kidney
Bean Stem Rot
Kidney bean (cultivar: Taisyou Kintoki) was
cultivated in a plastic pot having a diameter of 15 cm,
and when the main leaf developed sufficiently, 10 ml of a
chemical solution having the acid amide derivative of the
formula (I) or a salt thereof adjusted to a prescribed
concentration, was applied by a spray gun. After the
chemical solution dried (the same day as the application
or the next day), mycelial disc of Sclerotinia
sclerotiorum was inoculated and maintained in a constant
temperature chamber at 20°C. Three days after the
inoculation, the length of lesions (mm) was investigated,
and the controlling index was determined in accordance
with the above evaluation standards. The test was
carried out with respect to the above compoundsl-1, 1-4,
1-7, 1-10, 1-16, 1-18, 1-19, 1-21, 1-26, 1-30 to 1-33, 1-
36, 1-38, 1-42, 1-44, 1-46, 1-57, 1-60, 1-64, 1-69, 1-71,
1-73, 1-75, 1-80, 1-86, 1-93, 1-96 to 1-98, 1-103 to 1-
105, 1-108, 1-111 to 1-114, 1-117, 1-118, 1-123, 1-126,
1-128, 1-129, 1-133 to 1-136, 1-141 to 1-144, 1-146, 1-

149, 1-150, 1-159, 1-161 to 1-163, 1-165 to 1-171, 1-176,
1-180, 1-181, 1-186, 1-188, 1-208, 1-209, 1-271, 1-273,
1-276, 1-535,. 2-1, 2-3, 2-4, .2-10, 2-11, 2-13, 3-2, 3-3,
3-6, 3-23, 3-26, 4-10, 6-2, 6-3, 7-2, 7-4, 7-6 to 7-8,
and 7-66, and all compounds showed effects with a
controlling index of 4 or 5 at a concentration of 500
ppm.
TEST EXAMPLE 6: Test on Preventive Effect Against Wheat
Glume Blotch
Wheat (cultivar: Norin-61-go) was cultivated in a
plastic pot having a diameter of 7.5 cm, and when it
reached 1.5-leaf stage, 10 ml of a chemical solution
having the acid amide derivative of the formula (I) or a
salt thereof adjusted to a prescribed concentration, was
applied by a spray gun. After the chemical solution
dried (the same day as the application), a suspension of
conidia of Septoria nodorum was sprayed and inoculated
and maintained in an inoculation box at 20°C for 72 hours
and thereafter maintained in a constant temperature
chamber at 2 0°C. From 5 to 10 days after the
inoculation, the number of lesions was investigated, and
the controlling index was determined in accordance with
the above evaluation standards. The test was carried out
with respect to the above compounds No. 1-179 and 1-189,
and all compounds showed effects with a controlling index
of 4 or 5 at a concentration of 500 ppm.
TEST EXAMPLE 7: Test on Preventive Effect Against Rice

Sheath Blight
Rice (cultivar: Nihonbare) was cultivated in a
plastic pot having a diameter of 7.5 cm, and when it
reached 5-leaf stage, 10 ml of a chemical solution having
the acid amide derivative of the formula (I) or a salt
thereof adjusted to a prescribed concentration, was
applied by a spray gun. After the chemical solution
dried (the same day as the application or next day),
mycelial disc of Rhizoctonia solani preliminarily
cultured, was inserted in a leaf sheath and fixed by a
string, and maintained in an inoculation box at 25°C.
From 5 to 7 days after the inoculation, the length of
lesions was investigated, and the controlling index was
determined in accordance with the above evaluation
standards. The test was carried out with respect to the
above compounds No. 1-130, 1-137 and 3-3, and all
compounds showed effects with a controlling index of 4 or
5 at a concentration of 500 ppm.
Now, Formulation Examples of the composition of the
present invention will be described below. However, the
weight ratio, type of formulation or the like is by no
means restricted to the following Examples.
FORMULATION EXAMPLE 1
(1) Compound of the formula (I)
2 0 parts by weight
(2) Clay 72 parts by weight
(3) Sodium lignin sulfonate 8 parts by weight

The above components are uniformly mixed to obtain a
wettable powder.
FORMULATION EXAMPLE 2
(1) Compound of the formula (I)
5 parts by weight
(2) Talc 95 parts by weight
The above components are uniformly mixed to obtain a
dust.
FORMULATION EXAMPLE 3
(1) Compound of the formula (I)
20 parts by weight
(2) N,N'-dimethylacetamide 20 parts by weight
(3) Polyoxyethylene alkyl phenyl ether
10 parts by weight
(4) Xylene 50 parts by weight
The above components are uniformly mixed and
dissolved to obtain an emulsifiable concentrate.
FORMULATION EXAMPLE 4
(1) Clay 68 parts by weight
(2) Sodium lignin sulfonate 2 parts by weight
(3) Polyoxyethylene alkyl aryl sulfate
5 parts by weight
(4) Fine silica 25 parts by weight
A mixture of the above components and the compound
of the formula (I) are mixed in a weight ratio of 4:1 to
obtain a wettable powder.

FORMULATION EXAMPLE 5
(1) Compound of the formula (I)
50 parts by weight
(2) Oxylated polyalkylphenyl phosphate-
triethanolamine 2 parts by weight
(3) Silicone 0.2 part by weight
(4) Water 47.8 parts by weight
The above components are uniformly mixed and
pulverized to obtain a stock solution, and
(5) Sodium polycarboxylate 5 parts by weight
(6) Anhydrous sodium sulfate 42.8 parts by weight
are further added thereto, followed by uniform mixing,
granulation and drying to obtain a water-dispersible
granules.
FORMULATION EXAMPLE 6
(1) Compound of the formula (I)
5 parts by weight
(2) Polyoxyethylene octylphenyl ether
1 part by weight
(3) Phosphate of polyoxyethylene
0.1 part by weight
(4) Particulate calcium carbonate
93.9 parts by weight
The above components (1) to (3) are preliminarily
mixed uniformly and diluted with a proper amount of
acetone, the diluted mixture is sprayed on the component
(4), and acetone is removed to obtain granules.

FORMULATION EXAMPLE 7
(1) Compound of the formula (I)
2.5 parts by weight
(2) N-methyl-2-pyrrolidone 2.5 parts by weight
(3) Soybean oil 95.0 parts by weight
The above components are uniformly mixed and
dissolved to obtain an ultra low volume formulation.
FORMULATION EXAMPLE 8
(1) Compound of the formula (I)
20 parts by weight
(2) Oxylated polyalkylphenol phosphate
triethanolamine 2 parts by weight
(3) Silicone 0.2 part by weight
(4) Xanthan gum 0.1 part by weight

(5) Ethylene glycol 5 parts by weight
(6) Water 72.7 parts by weight
The above components are uniformly mixed and
pulverized to obtain a water-based suspension
concentrate.


WE CIAIM:
1. A fungicidal composition containing an acid amide
derivative of the formula (I) or a salt thereof as an
active ingredient:

wherein
A is phenyl which may be substituted by X,
benzodioxolanyl which may be substituted by X, or
benzodioxanyl which may be substituted by X;
B is furyl which may be substituted by Y, or
thienyl which may be substituted by Y,
each of R1 and R2
is alkyl, or
R1 and R2 may together form a 3- to 6-membered saturated
carbocyclic ring;
X is fluorine, chlorine, iodine, alkyl, haloalkyl,
alkoxy, or haloalkoxy;
Y is halogen, alkyl, haloalkyl, alkoxy, or haloalkoxy;
R3 is hydrogen; and
each of W1 and W2 is oxygen.
2. The fungicidal composition as claimed in claim 1,
wherein B is furyl substituted by Y.
3. The fungicidal composition as claimed in claim 1,

wherein B is thienyl substituted by Y.
4. The mixed fungicidal composition comprising an acid
amide derivatire of the formula (I) or salt thereof as
claimed in Claim 1, optionally comprising at least one
member of another fungicidally active ingredient
compound selected from the group consisting of an
anilinopyrimidine compound, a pyridinamine compound, an
azole compound, a guinoxaline compound, a dithiocarbamate
compound, an organic chlorine compound, an imidazole
compound, a cyano acetamide compound, a phenylamide
compound, a sulfenic acid compound, a copper compound, an
isoxazole compound, an organic phosphorus compound, an N-
halogenothioalkyl compound, a dicarboxyimide compound, a
benzanilide compound, an anilide compound, a piperazine
compound, a pyridine compound, a carbinol compound, a
piperidine compound, a morpholine compound, an organic
tin compound, an urea compound, a cinnamic acid compound,
a phenylcarbamate compound, a cyanopyrrole compound, a
strobilurin compound, an oxazolidinone compound, a
thiazolecarboxamide compound, a silylamide compound, an
amino acid amide carbamate compound, an imidazolidine
compound, a hydroxyanilide compound, a benzenesulfonamide
compound, an oxime ether compound, a phenoxyamide
compound, an antibiotic, a guanidine compound,
isoprothiolane, pyroquilon, diclomezine, quinoxyfen,
propamocarb hydrochloride, spiroxamine, chloropicrin,
dazomet, metam-sodium, nicobifen, metrafenone, MTF-753,

UBF-307, diclocymet, proquinazid, NC-224, KIF-7767 and
Syngenta 446510.
5. An acid amide derivative of the formula (I) or a
salt thereof:

wherein
A is phenyl which may be substituted by X,
benzodioxolanyl which may be substituted by X, or
benzodioxanyl which may be substituted by X;
B is furyl which may be substituted by Y, or
thienyl which may be substituted by Y,
each of R1 and R2
is alkyl, or
R1 and R2 may together form a 3- to 6-membered saturated
carbocyclic ring;
X is fluorine, chlorine, iodine, alkyl, haloalkyl,
alkoxy, or haloalkoxy;
Y is halogen, alkyl, haloalkyl, alkoxy, or haloalkoxy;
R3 is hydrogen; and
each of W1 and W2 is oxygen.
6. The acid amide derivative as claimed in claim 5,
wherein B is furyl substituted by Y.
7. The acid amide derivative as claimed in claim 5,
wherein B is thienyl substituted by Y.

8. The composition as claimed in any of claims 1-4,
wherein said composition is useful as a agricultural or
horticultural fungicide for controlling noxious fungi
selected from Oomycetes, Ascomycetes, Basidiomycetes or
Deuteromycetes.
9. The composition as claimed in claim 8, wherein
noxious fungi is Ascomycetes or Deuteromycetes.


The invention discloses an acid amide derivative of
formula (I) or a salt thereof, wherein R1, R2, R3, W1, W2,
A and B are as defined in the specification.

The invention is also for a fungicidal composition
comprising said compound.

Documents:

00404-kolnp-2007 assignment.pdf

00404-kolnp-2007 correspondence-1.1.pdf

0404-kolnp-2007 abstract.pdf

0404-kolnp-2007 claims.pdf

0404-kolnp-2007 correspondence others.pdf

0404-kolnp-2007 description(complete).pdf

0404-kolnp-2007 form-1.pdf

0404-kolnp-2007 form-3.pdf

0404-kolnp-2007 form-5.pdf

0404-kolnp-2007 g.p.a.pdf

0404-kolnp-2007 inertational publication.pdf

0404-kolnp-2007 international search authority report.pdf

0404-kolnp-2007 pct form.pdf

0404-kolnp-2007 priority document.pdf

404-KOLNP-2007-ABSTRACT.pdf

404-KOLNP-2007-AMANDED PAGES OF SPECIFICATION-1.1.pdf

404-KOLNP-2007-AMENDED PAGES OF SPECIFICATION.pdf

404-KOLNP-2007-ASSIGNMENT.pdf

404-KOLNP-2007-CLAIMS.pdf

404-KOLNP-2007-CORRESPONDENCE 1.1.pdf

404-KOLNP-2007-CORRESPONDENCE-1.2.pdf

404-KOLNP-2007-CORRESPONDENCE.pdf

404-KOLNP-2007-DESCRIPTION (COMPLETE).pdf

404-KOLNP-2007-ENGLISH TRANSLATION.pdf

404-KOLNP-2007-EXAMINATION REPORT REPLY RECIEVED.pdf

404-KOLNP-2007-EXAMINATION REPORT.pdf

404-KOLNP-2007-FORM 1.pdf

404-KOLNP-2007-FORM 13.pdf

404-KOLNP-2007-FORM 18 1.2.pdf

404-kolnp-2007-form 18.pdf

404-KOLNP-2007-FORM 2.pdf

404-KOLNP-2007-FORM 3.pdf

404-KOLNP-2007-FORM 5.pdf

404-KOLNP-2007-FORM-27.pdf

404-KOLNP-2007-GPA.pdf

404-KOLNP-2007-GRANTED-ABSTRACT.pdf

404-KOLNP-2007-GRANTED-CLAIMS.pdf

404-KOLNP-2007-GRANTED-DESCRIPTION (COMPLETE).pdf

404-KOLNP-2007-GRANTED-DRAWINGS.pdf

404-KOLNP-2007-GRANTED-FORM 1.pdf

404-KOLNP-2007-GRANTED-FORM 2.pdf

404-KOLNP-2007-GRANTED-SPECIFICATION.pdf

404-KOLNP-2007-OTHERS 1.1.pdf

404-kolnp-2007-others.pdf

404-KOLNP-2007-PETITION UNDER RULR 137.pdf

404-KOLNP-2007-REPLY TO EXAMINATION REPORT.pdf

404-KOLNP-2007-TRANSLATED COPY OF PRIORITY DOCUMENT.pdf

abstract-00404-kolnp-2007.jpg


Patent Number 249810
Indian Patent Application Number 404/KOLNP/2007
PG Journal Number 46/2011
Publication Date 18-Nov-2011
Grant Date 14-Nov-2011
Date of Filing 05-Feb-2007
Name of Patentee ISHIHARA SANGYO KAISHA, LTD.
Applicant Address 3-15, EDOBORI 1-CHOME, NISHI-KU, OSAKA-SHI OSAKA 5500002
Inventors:
# Inventor's Name Inventor's Address
1 NAKAMURA, YUJI C/O. ISHIHARA SANGYO KAISHA, LTD., CHUO KENKYUSHO,3-1, NISHI-SHIBUKAWA 2-CHOME, KUSATSU-SHI,SHIGA 5250025
2 YONEDA, TETSUO C/O. ISHIHARA SANGYO KAISHA, LTD., CHUO KENKYUSHO,3-1, NISHI-SHIBUKAWA 2-CHOME, KUSATSU-SHI,SHIGA 5250025
3 MITANI, SHIGERU C/O. ISHIHARA SANGYO KAISHA, LTD., CHUO KENKYUSHO,3-1, NISHI-SHIBUKAWA 2-CHOME, KUSATSU-SHI,SHIGA 5250025
PCT International Classification Number A01N 43/80,A01N 37/20 ,A01N 43/08
PCT International Application Number PCT/JP2005/014970
PCT International Filing date 2005-08-10
PCT Conventions:
# PCT Application Number Date of Convention Priority Country
1 2005-178614 2005-06-17 Japan
2 2004-235634 2004-08-12 Japan