N-[(fluoroalkoxy) phenoxyalkyl]benzamide compounds, intermediates thereof, process for producing the same, and agricultural and horticultural pesticides

Disclosed are A N-[(fluoroalkoxy)phenoxyalkyl]benzamide compound represented by the formula (1): ##STR1## wherein R.sup.1 and R.sup.3 may be the same or different and represent a hydrogen atom, a halogen atom, a C.sub.1-4 alkyl group, a C.sub.1-4 alkoxy group, a C.sub.1-4 haloalkyl group, a C.sub.1-4 haloalkoxy group, a cyano group, a nitro group, or a hydroxy group; R.sup.2 represents a hydrogen atom, a halogen atom, a C.sub.1-4 alkyl group, or a C.sub.1-4 alkoxy group; A represents an oxygen atom, or a sulfur atom; n is an integer of 1 to 6; x is 1 to 4; y is 0 to 6; z is 2 to 9; m is 0 to 2; provided that 2x+1=y+z+m, an intermediate thereof, processes thereof and an agricultural and horticultural chemical for controlling noxious organisms containing the above-mentioned compound as an effective ingredient which is available as a nematocide, an acaricide, a fungicide, etc.

TECHNICAL FIELD 
This invention relates to a novel N-[(fluoroalkoxy)-phenoxyalkyl]benzamide 
compound, intermediate, processes for preparing the same and an 
agricultural and horticultural chemical for controlling noxious organisms 
containing said compound as an effective ingredient useful as a 
nematocide, an acaricide and a fungicide. 
BACKGROUND ART 
As a benzamide derivative which is similar to the objective compound of the 
present invention, (1) and (2), etc. shown below have been known. 
(1) In Japanese Provisional Patent Publication No. 105784/1989, there is a 
disclosure about the compound represented by the following formula: 
##STR2## 
(wherein R and R.sup.1 each represent a hydrogen atom, a halogen atom, a 
nitro group, an alkyl group, an allyl group, a cycloalkyl group, an alkoxy 
group or an allyloxy group; Z represents an alkylene group with the carbon 
number of 2 to 4. Incidentally, the R, R.sup.1 and Z defined in this 
formula are limited only to this formula.) which is effective as a 
photographic material. 
(2) In Japanese Provisional Patent Publication No. 151546/1989, there is a 
disclosure about the compound represented by the following formula: 
##STR3## 
(wherein X represents O, S or NOH, R.sup.1 represents H or CH, n is 1, 2 
or 3, 
R.sup.2, R.sup.3 and R.sup.4 are defined by either of the following 
paragraphs: 
a) R.sup.2 and R.sup.3 are each Cl or Br, and R.sup.4 is H: 
b) R.sup.2, R.sup.3 and R.sup.4 are each Cl or Br: 
c) R.sup.2 is F, R.sup.3 is Cl, and R.sup.4 is H: or 
d) R.sup.2 and R.sup.3 are CH.sub.3 or C.sub.2 H.sub.5, and R.sup.4 is H, 
R.sup.5, R.sup.6 and R.sup.7 are defined by either of the following 
paragraphs: 
a) either R.sup.6 or R.sup.7 is CF.sub.3, and R.sup.5 and the other of 
R.sup.6 and R.sup.7 are H: 
b) R.sup.5 and R.sup.6 are H, and R.sup.7 is F, Cl or Br: 
c) R.sup.5 and R.sup.7 are each F, Cl or Br, and R.sup.6 is H: 
d) R.sup.5 and R.sup.6 are each F, Cl or Br, and R.sup.7 is H: 
e) R.sup.6 and R.sup.7 are each F, Cl or Br, and R.sup.5 is H: or 
f) R.sup.6 is phenoxy, and R.sup.5 and R.sup.7 are H. 
Incidentally, the R.sup.1 to R.sup.7, n and X defined in this formula are 
limited only to this formula.) which is effective as a fungicide. 
As a (fluoroalkoxy)phenoxyalkylamine derivative which is similar to the 
starting compound of the present invention, (3) to (6), etc. shown below 
have been known. 
(3) In Japanese Provisional Patent Publication No. 44846/1986, there is a 
disclosure about the compound represented by the following formula: 
##STR4## 
(wherein m and m' are each independently 0 or 1; n is an integer of 0 to 
3; R represents C.sub.1-4 alkyl, C.sub.2-8 alkenyl, C.sub.2-8 alkynyl, 
C.sub.1-8 haloalkyl, C.sub.2-8 haloalkenyl, C.sub.2-8 haloalkynyl, 
C.sub.2-10 alkoxyalkyl, C.sub.2-10 alkylthioalkyl, C.sub.3-8 cycloalkyl, 
C.sub.3-8 halocycloalkyl, C.sub.4-12 cycloalkylalkyl, heterocycloalkyl or 
heterocycloalkylalkyl; R.sup.1 to R.sup.4 and R.sup.8 are each 
independently hydrogen or C.sub.1-8 alkyl; R.sup.7 is C.sub.1-8 alkyl, 
C.sub.2-8 alkenyl, C.sub.2-8 alkynyl, C.sub.1-8 haloalkyl, C.sub.2-8 
haloalkenyl, C.sub.2-8 haloalkynyl, C.sub.3-8 cycloalkyl, C.sub.4-12 
cycloalkylalkyl or phenyl which are all unsubstituted, or a phenyl in 
which 1, 2 or 3-position of the carbon atom of the ring is substituted by 
a group selected from C.sub.1-8 alkyl, C.sub.1-8 haloalkyl, C.sub.1-8 
alkoxy, C.sub.1-8 haloalkoxy, halogen, nitro, cyano and C.sub.1- 8 
alkylthio, provided that when X.sup.1 is NR.sup.9, R.sup.7 can be also 
selected from a substituted or unsubstituted phenylthio and a 
S--C(SH.sub.3).sub.2 --CN group; R.sup.9 is a hydrogen atom, or that 
selected from the definition of R.sup.7 ; W represents oxygen, sulfur, 
NR.sup.8, CR.sup.3 R.sup.4 or carbonyl; W.sup.1 represents oxygen, sulfur, 
NR.sup.8, CR.sup.3 R.sup.4, carbonyl, sulfinyl or sulfonyl; X and Y are 
each oxygen, sulfur or NR.sup.8 ; X.sup.1 represents oxygen, sulfur or 
NR.sup.9 ; and Z represents C.sub.1-8 alkyl, C.sub.1-8 haloalkyl or 
halogen. Incidentally, the m, m', n, R, R.sup.1 to R.sup.9, W, W.sup.1, X, 
X.sup.1, Y and Z defined in this formula are limited only to this 
formula.) which is effective as an insecticide. 
(4) In Japanese Provisional Patent Publication No. 25 68470/1986, there is 
a disclosure about the compound represented by the following formula: 
##STR5## 
(wherein R.sup.1 represents a lower alkyl group, a lower alkoxy-lower 
alkyl group or a cycloalkyl group having the carbon number of 3 to 8; 
R.sup.2 represents a fluoro substituted-lower alkyl group; X represents an 
oxygen atom or a sulfur atom; Y represents a halogen atom or a lower alkyl 
group; m represents 0, 1 or 2; and n is an integer of 2 to 6. 
Incidentally, the R.sup.1, R.sup.2, X, Y, m and n defined in this formula 
are limited only to this formula.) which is effective as a fungicide. 
(5) In Japanese Provisional Patent Publication No. 149659/1987, there is a 
disclosure about the compound represented by the following formula: 
##STR6## 
(wherein R.sup.1 and R.sup.2 represent the same or different lower alkyl 
group; R.sup.3 and R.sup.4 represent the same or different lower alkyl 
group; R.sup.5 and R.sup.6 are the same or different and represent a 
hydrogen atom, a nitro group, a cyano group, a halogeno-lower alkyl group, 
a lower alkenyl group, a hydroxy group, a halogeno-lower alkoxy group, a 
lower alkenyloxy group, an aralkyloxy group, an aralkenyloxy group, a 
carboxyl group, a lower alkoxycarbonyl group, a group represented by the 
following formula: 
##STR7## 
(wherein R.sup.10 and R.sup.11 are the same or different and represent a 
hydrogen atom or a lower alkyl group. Provided that R.sup.10 and R.sup.11 
may form with the adjacent nitrogen atom a pyrrolidine ring, a piperidine 
ring, a morpholine ring, or a piperazine ring in which the nitrogen atom 
at the 4-position may be substituted by a lower alkyl group.) or a group 
represented by the following formula: 
##STR8## 
(wherein R.sup.10 and R.sup.11 are the same as defined above.); R.sup.7 
and R.sup.8 are the same or different and represent a hydrogen atom, a 
halogen atom, a cyano group, a lower alkyl group, a hydroxy group, a lower 
alkoxy group, a lower alkanoylamino group, or a naphthyl group fused with 
a benzene ring when it is adjacent to; A.sub.1 represents an alkylene 
group, an alkenylene group, or an alkynylene group; R.sup.9 represents a 
hydrogen atom or a lower alkyl group; B represents a single bond or 
CH.sub.2 O; and n represents 0, 1 or 2. Provided that when R.sup.5 and 
R.sup.6 are the same or different and represent a hydrogen atom or a nitro 
group, R.sup.9 represents a lower alkyl group or A.sub.1 represents a 
branched alkylene group, an alkenylene group or a branched alkynylene 
group. Incidentally, the R.sup.1 to R.sup.11, A.sub.1, B, m and n defined 
in this formula are limited only to this formula.) which has a calcium 
antagonism and a sympathetic nerve .beta.-acceptor blocking action. 
(6) In Japanese Provisional Patent Publication No. 142772/1990, there is a 
disclosure about the compound represented by the following formula: 
##STR9## 
(wherein Ar represents a phenyl group which is unsubstituted or 
substituted by one or more of halogen, C.sub.1-3 alkyl, C.sub.1-3 
haloalkyl, C.sub.2-4 alkenyl, C.sub.2-4 haloalkenyl, C.sub.1-3 alkoxy or 
C.sub.1-4 haloalkoxy as a substituent, or a pyridyl group which is 
unsubstituted or substituted by one or more of halogen or C.sub.1-3 
haloalkyl as a substituent; K, X and Z each independently represent O or 
S; B.sub.1 and B.sub.2 are the same or different and represent C.sub.1-6 
alkylidene; Rh.sub.1 represents C.sub.1-6 haloalkyl having 1 to 9 halogen 
atoms, C.sub.1-6 haloalkenyl having 1 to 9 halogen atoms, C.sub.3-8 
haloalkoxyalkyl, C.sub.3-8 haloalkoxyalkenyl (halogen is preferably 
fluorine); A represents a heterocyclic ring described in the following 
Table 1 (wherein R.sup.1 to R.sup.3 may be the same or different and 
represent H, C.sub.1-6 alkyl, C.sub.1-6 haloalkyl, C.sub.2-6 alkenyl, 
C.sub.2-6 haloalkenyl, C.sub.2-6 alkynyl, C.sub.2-6 haloalkynyl; G 
represents CH or N.). Incidentally, the Ar, K, X, Z, B.sub.1, B.sub.2, 
RH.sub.1, A, R.sup.1 to R.sup.3 and G defined in this formula are limited 
only to this formula.) which is effective as a fungicide. 
TABLE 1 
______________________________________ 
1 STR10## 
2 STR11## 
- 
3 STR12## 
4 #STR13## 
______________________________________ 
However, the disclosure of N-[(fluoroalkoxy)phenoxyalkyl]benzamide 
derivative and (fluoroalkoxy)phenoxyalkylamine derivative in which the 
amine portion is a (fluoroalkoxy)phenoxyalkylamino group as in the present 
invention cannot be admitted. 
Accordingly, the N-[(fluoroalkoxy)phenoxyalkyl]benzamide derivative and 
(fluoroalkoxy)phenoxyalkylamine derivative of the present invention are 
novel compounds, and it has been not known that the 
N-[(fluoroalkoxy)-phenoxyalkyl]benzamide derivative has an effect of 
controlling noxious organisms for agricultural and horticultural chemical 
which is available as a nematocide, an acaricide, fungicide, etc. 
DISCLOSURE OF THE INVENTION 
An object of the present invention is to provide an agricultural and 
horticultural chemical for controlling noxious organisms containing the 
novel N-[(fluoroalkoxy)-phenoxyalkyl]benzamide derivative as an effective 
ingredient, which is useful as a nematocide, an acaricide, a fungicide, 
etc. 
The present inventors have investigated to solve the above-mentioned 
problems, and as the results, they have found that the novel 
N-[(fluoroalkoxy)phenoxyalkyl]benzamide derivative has a remarkable 
controlling activity as an agricultural and horticultural chemical for 
controlling noxious organisms which is useful as a nematocide, an 
acaricide, a fungicide, etc., and thus, accomplished the present 
invention. 
That is, the present invention is as mentioned below. 
The first invention relates to a N-[(fluoroalkoxy)-phenoxyalkyl]benzamide 
derivative represented by the following formula (1): 
##STR14## 
wherein R.sup.1 represents a hydrogen atom, a halogen atom, an alkyl group 
having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, a 
haloalkyl group having 1 to 4 carbon atoms, a haloalkoxy group having 1 to 
4 carbon atoms, a cyano group, a nitro group, or a hydroxy group; 
R.sup.2 represents a hydrogen atom, a halogen atom, an alkyl group having 1 
to 4 carbon atom, or an alkoxy group having 1 to 4 carbon atom; 
R.sup.3 represents a hydrogen atom, a halogen atom, an alkyl group having 1 
to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, a haloalkyl 
group having 1 to 4 carbon atoms, a haloalkoxy group having 1 to 4 carbon 
atoms, a cyano group, or a nitro group; 
A represents an oxygen atom, or a sulfur atom; 
n represents an integer of 1 to 6; 
x represents an integer of 1 to 4; 
y represents an integer of 0 to 6; 
z represents an integer of 2 to 9; 
m represents an integer of 0 to 2; provided that 2x+1=y+z+m. 
The second invention relates to a process for preparing the 
N-[(fluoroalkoxy)phenoxyalkyl]benzamide derivative in which A represents 
an oxygen atom in the above-mentioned formula (1) which comprises reacting 
a (fluoroalkoxy)phenoxyalkylamine compound represented by the following 
formula (2): 
##STR15## 
wherein n, x, y, z and m have the same meanings as defined above, and a 
carboxylic acid compound represented by the following formula (3): 
##STR16## 
wherein R.sup.1 to R.sup.3 have the same meanings as defined above; and 
L.sup.1 represents a halogen atom, or a hydroxy group. 
The third invention relates to the (fluoroalkoxy)phenoxyalkylamine compound 
represented by the following formula (2): 
##STR17## 
wherein n, x, y ,z and m have the same meaning as defined above. 
The fourth invention relates to a process for preparing the 
(fluoroalkoxy)phenoxyalkylamine compound represented by the above formula 
(2) which comprises subjecting a (fluoroalkoxy)phenoxyalkyl compound 
represented by the following formula (4): 
##STR18## 
wherein L.sup.2 represents a halogen atom, a methanesulfonyloxy group, or 
a toluenesulfonyloxy group; n, x, y, z and m have the same meanings as 
defined above, to amination. 
The fifth invention relates to an agricultural and horticultural chemical 
for controlling noxious organisms containing the 
N-[(fluoroalkoxy)phenoxyalkyl]benzamide derivative represented by the 
above formula (1) as an effective ingredient. 
BEST MODE FOR PRACTICING THE INVENTION 
In the following, the present invention is explained in detail. 
R.sup.1 to R.sup.3, A, x, y, z, m, n, L.sup.1 and L.sup.2 shown in the 
novel N-[(fluoroalkoxy)phenoxyalkyl]benzamide compound (Compound (1)) and 
starting materials for producing the same (Compound (2) to Compound (5)) 
and L.sup.3 in the formula (6) mentioned below are as follows: (R.sup.1) 
As R.sup.1, there may be mentioned a hydrogen atom, a halogen atom, an 
alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 
carbon atoms, a haloalkyl group having 1 to 4 carbon atoms, a haloalkoxy 
group having 1 to 4 carbon atoms, a cyano group, a nitro group or a 
hydroxy group. 
As the halogen atom, a chlorine atom, an iodine atom, a bromine atom, a 
fluorine atom, etc. may be mentioned but a fluorine atom, a chlorine atom 
and a bromine atom are preferred. 
As the alkyl group, a straight or branched may be mentioned; but a methyl 
group is preferred. 
As the alkoxy group, a straight or branched may be mentioned; but a methoxy 
group is preferred. 
As the haloalkyl group, a straight or branched may be mentioned; and as the 
halogen atom, a chlorine atom, an iodine atom, a bromine atom, a fluorine 
atom, etc. may be mentioned, preferably a fluorine atom, and as the alkyl 
portion, it is preferably methyl. And as the haloalkyl group, it is 
preferably CF.sub.3. 
As the haloalkoxy group, a straight or branched may be mentioned; and as 
the halogen atom, a chlorine atom, an iodine atom, a bromine atom, a 
fluorine atom, etc. may be mentioned, preferably a fluorine atom, and as 
the alkyl portion, it is preferably methyl. And as the haloalkoxy group, 
it is preferably CHF.sub.2 O or CF.sub.3 O. (R.sup.2) 
As R.sup.2, there may be mentioned a hydrogen atom, a halogen atom, an 
alkyl group having 1 to 4 carbon atoms or an alkoxy group having 1 to 4 
carbon atoms. 
As the halogen atom, a chlorine atom, an iodine atom, a bromine atom, a 
fluorine atom, etc. may be mentioned but a fluorine atom is preferred. 
As the alkyl group, a straight or branched may be mentioned; but a methyl 
group is preferred. 
As the alkoxy group, a straight or branched may be mentioned; but a methoxy 
group is preferred. (R.sup.3) 
As R.sup.3, there may be mentioned a hydrogen atom, a halogen atom, an 
alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 
carbon atoms, a haloalkyl group having 1 to 4 carbon atoms, a haloalkoxy 
group having 1 to 4 carbon atoms, a cyano group or a nitro group. 
As the halogen atom, a chlorine atom, an iodine atom, a bromine atom, a 
fluorine atom, etc. may be mentioned. 
As the alkyl group, a straight or branched may be mentioned. 
As the alkoxy group, a straight or branched may be mentioned. 
As the haloalkyl group, a straight or branched may be mentioned; and as the 
halogen atom, a chlorine atom, an iodine atom, a bromine atom, a fluorine 
atom, etc. may be mentioned, preferably a fluorine atom, and as the alkyl 
portion, it is preferably methyl. And as the haloalkyl group, it is 
preferably CF.sub.3. 
As the haloalkoxy group, a straight or branched may be mentioned; and as 
the halogen atom, a chlorine atom, an iodine atom, a bromine atom, a 
fluorine atom, etc. may be mentioned, preferably a fluorine atom, and as 
the alkyl portion, it is preferably methyl. And as the haloalkoxy group, 
it is preferably CF.sub.3 O. 
The substitution position of R.sup.3 is not particularly limited but 
preferably 4-position. (OC.sub.x H.sub.y F.sub.z Cl.sub.m) 
x is an integer of 1 to 4, preferably 1 to 3. 
y is an integer of 0 to 6, preferably 0 to 4. 
z is an integer of 2 to 9, preferably 2 to 6. 
m is an integer of 0 to 2. 
Provided that 2x+1=y+z+m. 
The substitution position of OC.sub.x H.sub.y F.sub.z Cl.sub.m is not 
particularly limited but preferably 3-position or 4-position. (A) 
As A, an oxygen atom or a sulfur atom may be mentioned. (n) 
n is an integer of 1 to 6, preferably 2 to 5, further preferably 2 or 3. 
(L.sup.1 to L.sup.3) 
As L.sup.1, a halogen atom or a hydroxyl group may be mentioned, and the 
halogen atom may include a chlorine atom and a bromine atom. 
As L.sup.2 and L.sup.3, a halogen atom, a methanesulfonyloxy group or a 
toluenesulfonyloxy group may be mentioned, and the halogen atom may 
include a chlorine atom and a bromine atom. 
As the compound (1), those in which the above-mentioned various kinds of 
substituents are employed in combination may be mentioned, but preferred 
in view of pharmaceutical effects are as follows. 
(a) Compound (1) in which R.sup.1 to R.sup.3 are hydrogen atoms, OC.sub.x 
H.sub.y F.sub.z Cl.sub.m is 3-OC.sub.x F.sub.z or 4-OC.sub.x F.sub.z, A is 
an oxygen atom and n is 2. 
(b) Compound (1) in which R.sup.1 is a hydrogen atom, R.sup.2 and R.sup.3 
are hydrogen atoms, OC.sub.x H.sub.y F.sub.z Cl.sub.m is 3-OC.sub.x 
F.sub.z or 4-OC.sub.x F.sub.z, A is an oxygen atom and n is 2. 
(c) Compound (1) in which R.sup.1 and R.sup.2 are hydrogen atoms, R.sup.3 
is a halogen atom, OC.sub.x H.sub.y F.sub.z Cl.sub.m is 3-OC.sub.x F.sub.z 
or 4-OC.sub.x F.sub.z, A is an oxygen atom and n is 2. 
(d) Compound (1) in which R.sup.1 and R.sup.2 are halogen atoms, R.sup.3 is 
a hydrogen atom, OC.sub.x H.sub.y F.sub.z Cl.sub.m is 3-OC.sub.x F.sub.z 
or 4-OC.sub.x F.sub.z, A is an oxygen atom and n is 2. 
(e) Compound (1) in which R.sup.1 and R.sup.3 are halogen atoms, R.sup.2 is 
a hydrogen atom, OC.sub.x H.sub.y F.sub.z Cl.sub.m is 3-OC.sub.x F.sub.z 
or 4-OC.sub.x F.sub.z, A is an oxygen atom and n is 2. 
(f) Compound (1) in which R.sup.1 to R.sup.3 are halogen atoms, OC.sub.x 
H.sub.y F.sub.z Cl.sub.m is 3-OC.sub.x F.sub.z or 4-OC.sub.x F.sub.z, A is 
an oxygen atom and n is 2. 
(g) Compound (1) in which R.sup.1 is an alkyl group having 1 to 4 carbon 
atoms, R.sup.2 and R.sup.3 are hydrogen atoms, OC.sub.x H.sub.y F.sub.z 
Cl.sub.m is 3-OC.sub.x F.sub.z or 4-OC.sub.x F.sub.z, A is an oxygen atom 
and n is 2. 
(h) Compound (1) in which R.sup.1 is an alkoxy group having 1 to 4 carbon 
atoms, R.sup.2 and R.sup.3 are hydrogen atoms, OC.sub.x H.sub.y F.sub.z 
Cl.sub.m is 3-OC.sub.x F.sub.z or 4-OC.sub.x F.sub.z, A is an oxygen atom 
and n is 2. 
(i) Compound (1) in which R.sup.1 is a haloalkyl group having 1 to 4 carbon 
atoms, R.sup.2 and R.sup.3 are hydrogen atoms, OC.sub.x H.sub.y F.sub.z 
Cl.sub.m is 3-OC.sub.x F.sub.z or 4-OC.sub.x F.sub.z, A is an oxygen atom 
and n is 2. 
(j) Compound (1) in which R.sup.1 and R.sup.2 are halogen atoms, R.sup.3 is 
a hydrogen atom, OC.sub.x H.sub.y F.sub.z Cl.sub.m is 4-OC.sub.x H.sub.y 
F.sub.z, A is an oxygen atom and n is 2. 
(k) Compound (1) in which R.sup.1 and R.sup.2 are halogen atoms, R.sup.3 is 
a hydrogen atom, OC.sub.x H.sub.y F.sub.z Cl.sub.m is 4-OC.sub.x H.sub.y 
F.sub.z Cl.sub.m, A is an oxygen atom and n is 2. 
(l) Compound (1) in which R.sup.1 and R.sup.2 are halogen atoms, R.sup.3 is 
a hydrogen atom, OC.sub.x H.sub.y F.sub.z Cl.sub.m is 3-OC.sub.x F.sub.z 
or 4-OC.sub.x F.sub.z, A is a sulfur atom and n is 2. 
(m) Compound (1) in which R.sup.1 is a haloalkoxy group having 1 to 4 
carbon atoms, R.sup.2 and R.sup.3 are hydrogen atoms, OC.sub.x H.sub.y 
F.sub.z Cl.sub.m is 3-OC.sub.x F.sub.z or 4-OC.sub.x F.sub.z, A is an 
oxygen atom and n is 2. 
(n) Compound (1) in which R.sup.1 is a nitro group, R.sup.2 and R.sup.3 are 
hydrogen atoms, OC.sub.x H.sub.y F.sub.z Cl.sub.m is 3-OC.sub.x F.sub.z or 
4-OC.sub.x F.sub.z, A is an oxygen atom and n is 2. 
(o) Compound (1) in which R.sup.1 and R.sup.2 are an alkyl group having 1 
to 4 carbon atoms, R.sup.3 is a hydrogen atom, OC.sub.x H.sub.y F.sub.z 
Cl.sub.m is 3-OC.sub.x F.sub.z or 4-OC.sub.x F.sub.z, A is an oxygen atom 
and n is 2. 
(p) Compound (1) in which R.sup.1 and R.sup.2 are an alkoxy group having 1 
to 4 carbon atoms, R.sup.3 is a hydrogen atom, OC.sub.x H.sub.y F.sub.z 
Cl.sub.m is 3-OC.sub.x F.sub.z or 4-OC.sub.x F.sub.z, A is an oxygen atom 
and n is 2. 
(q) Compound (1) in which R.sup.1 is a hydroxyl group, R.sup.2 and R.sup.3 
are hydrogen atoms, OC.sub.x H.sub.y F.sub.z Cl.sub.m is 3-OC.sub.x 
F.sub.z or 4-OC.sub.x F.sub.z, A is an oxygen atom and n is 2. 
(r) Compound (1) in which R.sup.1 is a hydroxyl group, R.sup.2 is a 
hydrogen atom, R.sup.3 is a halogen atom, OC.sub.x H.sub.y F.sub.z 
Cl.sub.m is 3-OC.sub.x F.sub.z or 4-OC.sub.x F.sub.z, A is an oxygen atom 
and n is 2. 
(s) Compound (1) in which R.sup.1 and R.sup.3 are halogen atoms, R.sup.2 is 
a hydrogen atom, OC.sub.x H.sub.y F.sub.z Cl.sub.m is 3-OC.sub.x H.sub.y 
F.sub.z Cl.sub.m or 4-OC.sub.x F.sub.z, A is an oxygen atom and n is 3. 
As Compound (1) represented by these (a) to (s), preferred ones shown at 
the explanation for the above-mentioned R.sup.1 to R.sup.3, A, x, y, z, m, 
and n, and more preferred ones may be exemplified. 
Specific compounds (1) of these may include Compounds {(1-1) to (1-4), 
(1-8), (1-10), (1-13) to (1-17), (1-19), (1-30), (1-35), (1-38), (1-40), 
(1-43), (1-46), (1-52), (1-53), (1-55), (1-56)} described in the following 
Table 3, etc. 
As preferred embodiments for producing the 
N-[(fluoroalkoxy)phenoxyalkyl]benzamide compound represented by the above 
formula (1), in addition to the synthetic method 1 described as the second 
invention, the following two kinds of methods (Synthetic methods 2 and 3) 
may be mentioned. (Synthetic method 2) 
A process for producing a N-[(fluoroalkoxy)phenoxyalkyl]benzamide compound 
represented by the above formula (1) which comprises reacting a benzamide 
compound represented by the following formula (5): 
##STR19## 
wherein R.sup.1 to R.sup.3, A and n are the same as mentioned above, with 
a fluoroalkyl compound represented by the following formula (6): 
EQU C.sub.x H.sub.y F.sub.z Cl.sub.m --L.sup.3 (6) 
wherein represents a halogen atom, a methanesulfonyl group and a 
toluenesulfonyloxy group; x, y and z have the same meanings as defined 
above, in the presence of a base. 
(Synthetic Method 3) 
A process for producing a N-[(fluoroalkoxy)phenoxyalkyl]benzamide compound 
(referred to as Compound (1-b)) in which A represents a sulfur atom in the 
above-mentioned formula (1) which comprises reacting a compound (1a) 
represented by the following formula (1a): 
##STR20## 
wherein R.sup.1 to R.sup.3, x, y, z, m and n have the same meanings as 
mentioned above, in the presence of a sulfurizing agent. 
The above-mentioned synthetic methods 1 to 3 of Compound (1) of the present 
invention will be explained in more detail. 
(Synthetic Method 1) 
The synthetic method is as shown in Synthetic method 1, Compound (2) and 
Compound (3) are reacted in the presence of a base or a condensing agent 
in a solvent or without any solvent or a condensing agent to obtain the 
desired compound (1a) (A compound in which A in Compound (1) is 
represented by the formula (1). 
##STR21## 
wherein R.sup.1 to R.sup.3, x, y, z, m and n have the same meanings as 
mentioned above, 
(1) In case where L.sup.1 is a halogen atom 
The above process can be performed by reacting Compound (2) and Compound 
(3) in a solvent or without solvent, in the presence of a base. 
As the kinds of the solvent, it is not particularly limited so long as it 
does not directly participate the present reaction, and it may include, 
for example, an aromatic, aliphatic or alicyclic hydrocarbons such as 
benzene, toluene, xylene, methylnaphthalene, petroleum ether, ligroin, 
hexane, chlorobenzene, dichlorobenzene, methylene chloride, chloroform, 
dichloroethane, trichloroethylene, cyclohexane, etc.; ethers such as 
diethyl ether, tetrahydrofuran, dioxane, etc.; ketones such as acetone, 
methyl ethyl ketone, etc.; nitrites such as acetonitrile, propionitrile, 
etc.; organic bases such as triethylamine, pyridine, N,N-dimethylaniline, 
etc.; polar solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, 
dimethyl-sulfoxide, dimethylimidazolidinone, etc.; water; mixture of the 
above mentioned solvents, etc. 
Among these solvents, preferred are hydrocarbons and ethers. 
An amount of the solvent may preferably set so as to become Compound (2) 
being 5 to 80% by weight; preferably 10 to 70% by weight. 
A molar ratio of the starting materials can be set optionally, but usually 
Compound (3) is used in a ratio of 0.5 to 2 moles per 1 mole of Compound 
(2). 
The kind of the base is not specifically limited, and, for example, organic 
bases such as triethylamine, pyridine, N,N-dimethylaniline, 
1,8-diazabicyclo[5.4.0]-7-undecene (DBU), etc.; and inorganic bases such 
as sodium hydride, sodium amide, sodium hydroxide, potassium hydroxide, 
sodium carbonate, sodium hydrogen carbonate, potassium carbonate, etc. may 
be mentioned 
An amount of the base to be used is 1 to 10-fold mole based on Compound (2) 
and preferably 1 to 5-fold mole. 
The reaction temperature is not particularly limited, but a temperature 
range of from an ice-cooling temperature to the boiling point of the 
solvent to be used or less, preferably 0 to 30.degree. C. 
The reaction time may vary depending on the above-mentioned concentration 
and the temperature, but it is usually 0.1 to 2 hours. 
The starting Compound (2) can be obtained as shown below by reacting 
Compound (4) and potassium phthalimide in a solvent (First step), and then 
reacting a hydrazine (Second step). 
##STR22## 
wherein L.sup.2, n, x, y, z and m have the same meaning as defined above. 
First Step 
The kind of the solvent to be used in the first step is not particularly 
limited so long as it does not participate the present reaction directly, 
and, for example, hydrocarbons, ethers, ketones, nitrites, polar solvents 
and admixture of the above solvents as described in the above-mentioned 
(1) may be mentioned. 
An amount of potassium phthalimide is 1 to 10-fold mole based on Compound 
(4), preferably 1 to 5-fold mole. 
The reaction temperature is not particularly limited, but it is a 
temperature range of from an ice-cooling temperature to the boiling point 
of the solvent to be used or less, preferably 40 to 120.degree. C. 
The reaction time may vary depending on the above-mentioned concentration 
and the temperature, but it is usually 0.5 to 10 hours. 
Second Step 
The reaction with hydrazine can be carried out by isolating the phthalimide 
derivative obtained by the above-mentioned first step or without 
isolation. 
The kind of the solvent to be used in the second step is not particularly 
limited so long as it does not participate the present reaction directly, 
and, for example, hydrocarbons; ethers; polar solvents; alcohols such as 
methanol, ethanol, propanol, butanol, etc.; water; and admixture of the 
above-mentioned solvents as described in the above-mentioned (1) may be 
mentioned. 
An amount of hydrazine is 1 to 10-fold mole based on Compound (4), 
preferably 1 to 5-fold mole. 
The reaction temperature is not particularly limited, but it is a 
temperature range of from an ice-cooling temperature to the boiling point 
of the solvent to be used or less, preferably 40 to 120.degree. C. 
The reaction time may vary depending on the above-mentioned concentration 
and the temperature, but it is usually 0.5 to 10 hours. 
Compound (2) prepared as mentioned above is subjected to the usual 
post-treatment such as extraction, concentration, filtration, etc. after 
completion of the reaction, and optionally purified by the well-known 
means such as recrsytallization, various kinds of chromatographies, etc., 
if necessary. 
Compound (4) can be obtained by subjecting the reaction as mentioned below. 
##STR23## 
wherein n, x, y, z, m and L.sup.2 have the same meanings as defined above. 
Also, Compound (4) can be also obtained by carrying out the reaction as 
mentioned below. 
##STR24## 
wherein n, x, y, z, m and L.sup.2 have the same meanings as defined above. 
As Compound (3), a commercially available product can be used. 
(2) When L.sup.1 is a hydroxyl group 
The above-mentioned process can be performed by reacting Compound (2) and 
Compound (3) in a solvent or without solvent in the presence of a 
condensing agent. 
The kind of the solvent is not particularly limited so long as it does not 
participate the present reaction directly, and, for example, hydrocarbons, 
ethers, ketones, nitrites, polar solvents and admixture of the above 
solvents which are the same as described in the above-mentioned (1) may be 
used. 
An amount of the solvent may be so used that Compound (2) becomes 5 to 80% 
by weight; preferably 10 to 70% by weight. 
A ratio of the starting materials can be set optionally, but usually 
Compound (3) is in a ratio of 0.5 to 2 moles based on 1 mole of Compound 
(2). 
The kind of the dehydrating agent is not particularly limited, and for 
example, there may be mentioned dicyclohexylcarbodiimide (DCC), 
diethylazodicarboxylate, diisopropylazodicarboxylate, 
1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide hydrochloride (WSC), 
1,1'-carbonyldiimidazole, sulfuric acid, phosphorus pentachloride, etc. 
An amount of the dehydrating agent is 1 to 10-fold mole based on Compound 
(2), and preferably 1 to 5-fold mole. 
The reaction temperature is not particularly limited, but it is a 
temperature range of from an ice-cooling temperature to the boiling point 
of the solvent to be used or less, preferably 0 to 50.degree. C. 
The reaction time may vary depending on the above-mentioned concentration 
and the temperature, but it is usually 0.5 to 8 hours. 
Compound (1a) prepared as mentioned above is subjected to the usual 
post-treatment such as extraction, concentration, filtration, etc. after 
completion of the reaction, and optionally purified by the well-known 
means such as recrsytallization, various kinds of chromatographies, etc., 
if necessary. 
(Synthethic Method 2) 
Synthetic method 2 is as shown below a method of obtaining Compound (1a) (a 
compound in Compound (1) where A is represented by an oxygen atom) by 
reacting Compound (5) and Compound (6) in a solvent in the presence of a 
base. 
##STR25## 
wherein R.sup.1 to R.sup.3, n, x, y, z, m and L.sup.3 have the same 
meanings as defined above. 
The kind of the solvent is not particularly limited so long as it does not 
participate the present reaction directly, and, for example, hydrocarbons, 
ethers, ketones, nitrites, polar solvents and admixture of the above 
solvents which are the same as described in the above-mentioned Synthetic 
method 1 may be mentioned. 
An amount of the solvent may be so used that Compound (5) becomes 5 to 80% 
by weight; preferably 10 to 70% by weight. 
The kind of the base is not particularly limited and there may be 
mentioned, for example, the organic base and the inorganic base mentioned 
in the above (1), and preferably sodium hydroxide and potassium hydroxide. 
An amount of the base is 1 to 10-fold moles based on Compound (5) and 
preferably 2 to 5-fold moles. 
The reaction temperature is not particularly limited, but it is a 
temperature range of from an ice-cooling temperature to the boiling point 
of the solvent to be used or less, preferably 0 to 100.degree. C. 
The reaction time may vary depending on the above-mentioned concentration 
and the temperature, but it is usually 0.5 to 3 hours. 
Also, when the materials are reacted in a two-layer system of an organic 
solvent and water, the reaction can be promoted by using a phase-transfer 
catalyst. 
The phase-transfer catalyst is not particularly limited, and there may be 
mentioned, for example, tetrabutylammonium bromide, benzyltriethylammonium 
chloride, tricaprylylmethylammonium chloride, etc. 
An amount of the phase-transfer catalyst is 0.01 to 5-fold moles based on 
Compound (5), preferably 0.05 to 0.5-fold mole. 
Compound (1a) prepared as mentioned above is subjected to the usual 
post-treatment such as extraction, concentration, filtration, etc. after 
completion of the reaction, and optionally purified by the well-known 
means such as recrsytallization, various kinds of chromatographies, etc., 
if necessary. 
Compound (5) can be obtained by effecting the reaction as mentioned below. 
##STR26## 
wherein R.sup.1 to R.sup.3 and n have the same meanings as defined above. 
As Compound (6), a commercially available product may be used, but it can 
be also obtained by effecting the reaction as mentioned below. 
##STR27## 
wherein x, y, z, m and L.sup.3 have the same meanings as defined above. 
(Synthetic Method 3) 
Synthetic method 3 is a method, as mentioned below, in which Compound (1b) 
(a compound in which A in Compound (1) is shown by a sulfur atom) is 
obtained by reacting Compound (1a) in a solvent in the presence of a 
sulfurizing agent. 
##STR28## 
wherein R.sup.1 to R.sup.3, n, x, y, z and m have the same meanings as 
defined above. 
The kind of the solvent is not particularly limited so long as it does not 
participate the present reaction directly, and, for example, hydrocarbons, 
ethers and admixture of the above solvents which are the same as described 
in the above-mentioned Synthetic method 1 may be mentioned. 
An amount of the solvent may be so used that Compound (1a) becomes 5 to 80% 
by weight; preferably 10 to 70% by weight. 
The kind of the sulfurizing agent is not particularly limited and there may 
be mentioned, for example, phosphorus pentasulfate, 
2,4-bis(4-methoxyphenyl)-1,3-dithia-2,4-diphosphetan-2,4-disulfide 
(Lawesson's reagent), hydrogen sulfide, etc. 
An amount of the sulfurizing agent is 1 to 10-fold moles based on Compound 
(1a) and preferably 1 to 5-fold moles. 
The reaction temperature is not particularly limited, but it is a 
temperature range of from an ice-cooling temperature to the boiling point 
of the solvent to be used or less, preferably 40 to 120.degree. C. 
The reaction time may vary depending on the above-mentioned concentration 
and the temperature, but it is usually 0.5 to 10 hours. 
Compound (1b) prepared as mentioned above is subjected to the usual 
post-treatment such as extraction, concentration, filtration, etc. after 
completion of the reaction, and optionally purified by the well-known 
means such as recrystallization, various kinds of chromatographies, etc., 
if necessary. 
As the agricultural and horticultural noxious organisms on which a 
controlling effect by the compound (I) of the present invention can be 
observed, there may be mentioned agricultural and horticultural noxious 
insects (e.g. Hemiptera (planthoppers, leafhoppers, aphides, white-flies, 
etc.), Lepidoptera (cabbage armyworms, diamond-back moth, leafroller 
moths, pyralid moths, common cabbage worm, etc.), Coleoptera (Tenebrionid 
beetles, leafbeetles, weevils, scarabs,.etc.) and Acarina (citrus red 
mite, two-spotted spider mite, etc. of Tetranychidae family, pink citrus 
rust mite of Eriophyidae family, etc.)), hygienically noxious insects 
(e.g. flies, mosquitoes, cockroaches, etc.), noxious insects of stored 
grains (rust-red flour beetles, bean weevils, etc.), and root knot 
nematode, pine wood nematode and bulb mite in soil, and also agricultural 
and horticultural diseases (e.g. wheat brown rust, barley powdery mildew, 
cucumber downy mildew, rice blast, tomato late blight, etc.). 
The agricultural and horticultural chemical for controlling noxious 
organisms of the present invention is particularly remarkable in 
nematocidal, acaricidal and fungicidal effect and contains at least one 
kind of Compound (1) as an effective ingredient. 
Compound (1) may be used singly, but usually, it is preferred to formulate 
a carrier, surfactant, dispersant, auxiliary, etc. (for example, it is 
prepared as a composition such as dust powder, an emulsifiable 
concentrate, a fine granule, a granule, a wettable powder, an oily 
suspension, an aerosol, etc.) according to the conventionally known 
method. 
As the carrier, there may be mentioned, for example, a solid carrier such 
as bentonite, clay, kaolin, diatomaceous earth, white carbon, vermiculite, 
calcium hydroxide, siliceous sand, ammonium sulfate,.urea, etc., a liquid 
carrier such as hydrocarbon (kerosine, mineral oil, etc.), aromatic 
hydrocarbon, (benzene, toluene, xylene, etc.), chlorinated hydrocarbon 
(chloroform, carbon tetrachloride, etc.), ethers (dioxane, 
tetrahydrofuran, etc.), ketones (acetone, cyclohexanone, isophorone, 
etc.), esters (ethyl acetate, ethyleneglycol acetate, dibutyl maleate, 
etc.), alcohols (methanol, n-hexanone, ethylene glycol, etc.), polar 
solvent (dimethylformamide, dimethylsulfoxide, etc.), water, etc.; a gas 
carrier such as air, nitrogen, a carbonic acid gas, fleone, etc. (in this 
case, mixture spreading can be carried out), and the like. 
As the surfactant and dispersant which can be used for improving attachment 
of the present chemical to and absorption thereof in animals and plants, 
and improving characteristics such as dispersion, emulsification and 
spreading of the chemical, there may be mentioned, for example, alcohol 
sulfates, alkylsulfonate, lignosulfonate and polyoxyethylene glycol ether. 
Further, for improving properties of its formulation, for example, 
carboxymethyl cellulose, polyethylene glycol and gum arabic can be used as 
an auxiliary. 
In preparation of the present chemical, the above carrier, surfactant, 
dispersant and auxiliary can be used singly or in a suitable combination, 
respectively, depending on the respective purposes. 
When the compound (I) of the present invention is made into formulations, 
the concentration of the active ingredient is generally 1 to 50% by weight 
in an emulsifiable concentrate, generally 0.3 to 25% by weight in a 
dustable powder, generally 1 to 90% by weight in a wettable powder, 
generally 0.5 to 5% by weight in a granule, generally 0.5 to 5% by weight 
in an oily suspension, and generally 0.1 to 5% by weight in an aerosol. 
These formulations can be provided for various uses by diluting them to 
have a suitable concentration and spraying them to stems and leaves of 
plants, soil and paddy field surface, or by applying them directly 
thereto, depending on the purposes.

EXAMPLES 
In the following, the present invention is explained by referring to 
Examples more specifically. These Examples are not intended to limit the 
scope of the present invention. 
Example 1 
(Synthesis of Compound (2)) 
(1) Synthesis of 2-(4-trifluoromethoxyphenoxy)ethylamine (Compound (2-2)) 
In N,N-dimethylformamide (20 ml) was dissolved methanesulfonic acid 
2-(4-trifluoromethoxyphenoxy)ethyl ester (3.00 g), then potassium 
phthalimide (2.04 g) was added thereto and the mixture was stirred at 
100.degree. C. for 3 hours. 
After completion of the reaction, water (100 ml) was added to the mixture 
and the resulting mixture was stirred, and formed precipitates were taken 
out by filtration. 
The resulting precipitates were dissolved by adding ethanol (30 ml) under 
heating, then hydrazine hydrate (0.55 g) was added thereto and the mixture 
was refluxed for 3 hours under heating. 
After completion of the reaction, ethanol was removed under reduced 
pressure, then a 5N sodium hydroxide aqueous solution (50 ml) was added to 
the precipitates to dissolve the precipitates and the mixture was 
extracted with ethyl acetate. 
Then, the organic layer was washed with a saturated saline solution, dried 
over anhydrous sodium sulfate and the solvent was removed under reduced 
pressure, and the residue was purified by silica gel chromatography (Wako 
gel C-200, eluted by ethyl acetate and subsequently by ethanol) to obtain 
1.54 g of the title compound as a pale yellowish oily product. 
.sup.1 H-NMR (CDCl.sub.3, .delta. ppm) 
2.18 to 2.47 (2H, br), 3.11 (2H, t, J=5.1 Hz), 3.91 to 4.09 (2H, m), 6.88 
to 7.25 (4H, m) 
(2) Synthesis of 2-[4-(2,2,2-trifluoroethoxy)phenoxy]ethylamine (Compound 
(2-3)) 
In N,N-dimethylformamide (30 ml) was dissolved 
2-[4-(2,2,2-trifluoroethoxy)phenoxy]ethyl bromide (4.50 g), then potassium 
phthalimide (3.05 g) was added thereto and the mixture was stirred at 
100.degree. C. for 3 hours. 
After completion of the reaction, water (120 ml) was added to the mixture 
and the resulting mixture was stirred, and formed precipitates were taken 
out by filtration. 
The resulting precipitates were dissolved by adding ethanol (50 ml) under 
heating, then hydrazine hydrate (0.55 g) was added thereto and the mixture 
was refluxed for 3 hours under heating. 
After completion of the reaction, 5N hydrochloric acid (50 ml) was added to 
the mixture, and the resulting mixture was stirred and then filtered under 
heating. 
The resulting filtrate was washed with toluene, then the aqueous layer was 
made basic with a 5N sodium hydroxide aqueous solution, and the title 
compound was extracted with ethyl acetate. 
Then, the organic layer was washed with a saturated saline solution, dried 
over anhydrous sodium sulfate and the solvent was removed under reduced 
pressure to obtain 2.57 g of the title compound as a pale yellowish oily 
product. 
.sup.1 H-NMR (CDCl.sub.3, .delta. ppm) 
1.39 to 1.54 (2H, br), 2.95 to 3.13 (2H, m), 3.87 to 4.37 (4H, m), 6.74 to 
6.97 (4H, m) 
(3) Synthesis of 2-[4-(1,1,2,2-tetrafluoroethoxy)phenoxy]-ethylamine 
(Compound (2-5)) 
In N,N-dimethylformamide (10 ml) was dissolved methanesulfonic acid 
2-[4-(1,1,2,2-tetrafluoroethoxy)-phenoxy]ethyl ester (1.61 g), then 
potassium phthalimide (1.02 g) was added thereto and the mixture was 
stirred at about 100.degree. C. for 3 hours. 
After completion of the reaction, water (50 ml) was added to the mixture 
and formed precipitates were collected by filtration, and after 
pulverization the precipitates, they were washed with water. 
The resulting precipitates were dissolved by adding them to ethanol (20 ml) 
under heating, then hydrazine hydrate (0.28 g) was added thereto and the 
mixture was stirred for 3 hours under heating. 
After completion of the reaction, ethanol was removed under reduced 
pressure, then a 5N sodium hydroxide aqueous solution (30 ml) was added to 
the precipitates to dissolve the precipitates and the title compound was 
extracted with ethyl acetate. 
Then, the organic layer was washed with a saturated saline solution, dried 
over anhydrous sodium sulfate and ethyl acetate was removed under reduced 
pressure. The resulting oily product was purified by silica gel 
chromatography (Wako gel C-200, eluted by ethyl acetate to ethanol) to 
obtain 0.89 g of the title compound which is a pale yellowish oily 
product. 
.sup.1 H-NMR (CDCl.sub.3, .delta. ppm) 
1.82 to 2.19 (2H, br), 3.01 to 3.20 (2H, br), 3.98 (2H, t), 5.89 (1H, m), 
6.86 to 7.18 (4H, m) 
(4) Synthesis of 2-[4-(2-chloro-1,1,2-trifluoroethoxy)-phenoxy]ethylamine 
(Compound (2- 6)) 
In N,N-dimethylformamide (30 ml) was dissolved 
2-[4-(2-chloro-1,1,2-trifluoroethoxy)phenoxy]ethyl bromide (5.00 g), then 
potassium phthalimide (3.05 g) was added thereto and the mixture was 
stirred at 100.degree. C. for 3 hours. 
After completion of the reaction, water (120 ml) was added to the mixture 
and formed precipitates were taken out by filtration. 
The resulting precipitates were dissolved by adding them to ethanol (50 ml) 
under heating, then hydrazine hydrate (0.83 g) was added thereto and the 
mixture was stirred for 3 hours under heating. 
After completion of the reaction, 5N hydrochloric acid (70 ml) was added to 
the mixture, and the resulting mixture was stirred and then filtered under 
heating. 
The resulting filtrate was washed with toluene, subsequently the aqueous 
layer was made basic with a 5N sodium hydroxide aqueous solution and the 
title compound was extracted with ethyl acetate. 
Then, the organic layer was washed with a saturated saline solution, dried 
over anhydrous sodium sulfate and the solvent was removed under reduced 
pressure to obtain 2.73 g of the title compound which is a pale yellowish 
oily product. 
.sup.1 H-NMR (CDCl.sub.3, .delta. ppm) 
1.18 to 1.75 (2H, br), 2.95 to 3.14 (2H, m), 3.49 (2H, t, J=4.9 Hz), 6.14 
to 6.35 (1H, m), 6.74 to 7.26 (4H, m) (5) Synthesis of 
2-(3-trifluoromethoxyphenoxy)ethylamine (Compound (2-9)) 
In N,N-dimethylformamide (20 ml) was dissolved methanesulfonic acid 
2-(3-trifluoromethoxyphenoxy)ethyl ester (3.00 g), then potassium 
phthalimide (2.04 g) was added thereto and the mixture was stirred at 
100.degree. C. for 3 hours. 
After completion of the reaction, water (100 ml) was added to the mixture 
and formed precipitates were taken out by filtration. 
The resulting precipitates were dissolved by adding them to ethanol (30 ml) 
under heating, then hydrazine hydrate (0.55 g) was added thereto and the 
mixture was refluxed for 3 hours under heating. 
After completion of the reaction, 5N hydrochloric acid (50 ml) was added to 
the mixture, and the resulting mixture was stirred and then filtered under 
heating. 
The resulting filtrate was washed with toluene, subsequently the aqueous 
layer was made basic with a 5N sodium hydroxide aqueous solution and the 
title compound was extracted with ethyl acetate. 
Then, the organic layer was washed with a saturated saline solution, dried 
over anhydrous sodium sulfate and the solvent was removed under reduced 
pressure to obtain 1.76 g of the title compound which is a pale yellowish 
oily product. 
.sup.1 H-NMR (CDCl.sub.3, .delta. ppm) 
1.61 to 1.92 (2H, br), 3.09 (2H, t, J=5.1 Hz), 3.99 (2H, t, J=5.1 Hz), 6.67 
to 7.35 (4H, m) 
(6) Synthesis of 3-(4-trifluoromethoxyphenoxy)propylamine (Compound 
(2-10)). 
In N,N-dimethylformamide (20 ml) was dissolved methanesulfonic acid 
3-(4-trifluoromethoxyphenoxy)propyl ester (3.14 g), then potassium 
phthalimide (2.04 g) was added thereto and the mixture was stirred at 
100.degree. C. for 3 hours. 
After completion of the reaction, water (100 ml) was added to the mixture 
and formed precipitates were taken out by filtration. 
The resulting precipitates were dissolved by adding them to ethanol (30 ml) 
under heating, then hydrazine hydrate (0.55 g) was added thereto and the 
mixture was refluxed for 3 hours under heating. 
After completion of the reaction, 5N hydrochloric acid (50 ml) was added to 
the mixture, and the resulting mixture was stirred and then filtered under 
heating. 
The resulting filtrate was washed with toluene, subsequently the aqueous 
layer was made basic with a 5N sodium hydroxide aqueous solution and the 
title compound was extracted with ethyl acetate. 
Then, the organic layer was washed with a saturated saline solution, dried 
over anhydrous sodium sulfate and the solvent was removed under reduced 
pressure to obtain 1.68 g of the title compound which is a pale yellowish 
oily product. 
.sup.1 H-NMR (CDCl.sub.3, .delta. ppm) 
1.81 to 2.06 (2H, m), 2.22 to 2.51 (2H, Br), 2.93 (2H, t, J=6.6 Hz), 4.04 
(2H, t, J=5.9 Hz), 6.77 to 7.24 (4H, m) 
(7) Synthesis of other Compound (2) in Table 2 
In accordance with either one of the above-mentioned (1) to (6). other 
Compound (2) in Table 2 was synthesized. 
Compounds synthesized as mentioned above and physical properties thereof 
are shown in Table 2. 
TABLE 2 
______________________________________ 
5 (2) 9## 
Physical 
Compound OC.sub.x H.sub.y F.sub.z Cl.sub.m n properties 
______________________________________ 
2-1 4-OCHF.sub.2 
2 
2-2 4-OCF.sub.3 2 n.sub.D.sup.20.0 1.4654 
2-3 4-OCH.sub.2 CF.sub.3 2 n.sub.D.sup.20.0 1.4768 
2-4 4-OCF.sub.2 CFH.sub.2 2 
2-5 4-OCF.sub.2 CF.sub.2 H 2 n.sub.D.sup.20.0 1.4688 
2-6 4-OCF.sub.2 CFClH 2 n.sub.D.sup.20.0 1.4834 
2-7 4-OCF.sub.2 CHFCF.sub.3 2 
2-8 2-OCF.sub.3 2 
2-9 3-OCF.sub.3 2 n.sub.D.sup.20.0 1.4635 
2-10 4-OCF.sub.3 3 n.sub.D.sup.20.0 1.4676 
2-11 4-OCF.sub.3 5 
______________________________________ 
Example 2 
(Synthesis of Compound (1)) 
By using Compound (2) obtained in Example 1, the title compound (1) was 
synthesized. 
(1) Synthesis of N-[2-(4-trifluoromethoxyphenoxy)ethyl]-2-fluorobenzamide 
(Compound (1-2)) 
WSC (1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride) (1.10 g) 
was added to a dichloromethane (20 ml) solution of 
2-(4-trifluoromethoxyphenoxy)ethylamine (1.10 g) and 2-fluorobenzoic acid 
(0.70 g) and the mixture was stirred at room temperature for 3 hours. 
After completion of the reaction, water (10 ml) was added to the reaction 
mixture and extraction was carried out. The organic layer was washed with 
a saturated saline solution and dried over anhydrous sodium sulfate, and 
then the solvent was removed under reduced pressure. 
The resulting residue was purified by silica gel chromatography (Wako gel 
C-200, eluted by toluene : ethyl acetate=9:1) to obtain 1.21 g of the 
title compound as colorless crystal. 
.sup.1 H-NMR (CDCl.sub.3, .delta. ppm) 
3.87 to 4.22 (4H, m), 6.85 to 7.52 (8H, m), 8.06 to 8.14 (1H, m) 
(2) Synthesis of N-[2-(4-trifluoromethoxyphenoxy)ethyl]-2-chlorobenzamide 
(Compound (1-3)) 
A tetrahydrofuran (5 ml) solution of 2-chlorobenzoyl chloride (0.88 g) was 
added dropwise under ice-cooling and stirring to a tetrahydrofuran (20 ml) 
solution of 2-(4-trifluoromethoxyphenoxy)ethylamine (1.10 g) and 
triethylamine (0.51 g) and the mixture was further stirred at room 
temperature for one hour. 
After completion of the reaction, the formed triethylamine hydrochloride 
was removed by filtration, and the solvent was removed under reduced 
pressure. 
The resulting residue was purified by silica gel chromatography (Wako gel 
C-200, eluted by toluene:ethyl acetate=9:1) to obtain 1.53 g of the title 
compound as colorless crystal. 
.sup.1 H-NMR (CDCl.sub.3, .delta. ppm) 
3.78 to 4.22 (4H, m), 6.52 to 6.80 (1H, br), 6.80 to 7.87 (8H, m) 
(3) Synthesis of 
N-[2-(4-trifluoromethoxyphenoxy)ethyl]-2,6-difluorobenzamide Compound 
(1-10)) 
A tetrahydrofuran (5 ml) of 2,6-difluorobenzoyl chloride (0.88 g) was added 
dropwise under ice-cooling and stirring to a tetrahydrofuran (20 ml) 
solution of 2-(4-trifluoromethoxyphenoxy)ethylamine (1.10 g) and 
triethylamine (0.51 g) and the mixture was further stirred at room 
temperature for one hour. 
After completion of the reaction, the formed triethylamine hydrochloride 
was removed by filtration and the solvent was removed under reduced 
pressure. 
The resulting residue was purified by silica gel chromatography (Wako gel 
C-200, eluted by toluene:ethyl acetate =9:1) to obtain 1.48 g of the title 
compound as colorless crystal. 
.sup.1 H-NMR (CDCl.sub.3, .delta. ppm) 
3.78 to 4.22 (4H, m), 6.28 to 6.53 (1H, br), 6.78 to 7.47 (7H, m) 
(4) Synthesis of 
N-[2-(4-trifluoromethoxyphenoxy)ethyl]-2,4,6-trifluorobenzamide (Compound 
(1-14)) 
WSC (1.15 g) was added to a dichloromethane (20 ml) solution of 
2-(4-trifluoromethoxyphenoxy)ethylamine (1.10 g) and 
2,4,6-trifluorobenzoic acid (0.87 g) and the mixture was stirred at room 
temperature for 3 hours. 
After completion of the reaction, water (10 ml) was added to the reaction 
mixture and extraction was carried out. The organic layer was washed with 
a saturated saline solution and dried over anhydrous sodium sulfate, and 
then the solvent was removed under reduced pressure. 
The resulting residue was purified by silica gel chromatography (Wako gel 
C-200, eluted by toluene:ethyl acetate=9:1) to obtain 1.27 g of the title 
compound as colorless crystal. 
.sup.1 H-NMR (CDCl.sub.3, .delta. ppm) 
3.77 to 4.23 (4H, m), 6.26 to 6.48 (1H, br), 6.61 to 7.26 (6H, m) 
(5) Synthesis of N-[2-(4-trifluoromethoxyphenoxy)ethyl]-2-methylbenzamide 
(Compound (1-15)) 
A tetrahydrofuran (5 ml) solution of 2-methylbenzoyl chloride (0.77 g) was 
added dropwise under ice-cooling and stirring to a tetrahydrofuran (20 ml) 
solution of 2-(4-trifluoromethoxyphenoxy)ethylamine (1.10 g) and 
triethylamine (0.51 g) and the mixture was further stirred at room 
temperature for one hour. 
After completion of the reaction, the resulting triethylamine hydrochloride 
was removed by filtration, and then the solvent was removed under reduced 
pressure. 
The resulting residue was purified by silica gel chromatography (Wako gel 
C-200, eluted by toluene:ethyl acetate=9:1) to obtain 1.31 g of the title 
compound as colorless crystal. 
.sup.1 H-NMR (CDCl.sub.3, .delta. ppm) 
2.44 (3H, s), 3.75 to 4.20 (4H, m), 6.14 to 6.32 (1H, br), 6.80 to 7.41 
(8H, m) 
(6) Synthesis of 
N-[2-(4-trifluoromethoxyphenoxy)ethyl]-2-trifluoromethylbenzoylamide 
(Compound (1-17)) 
A tetrahydrofuran (5 ml) solution of 2-trifluoromethylbenzoyl chloride 
(1.04 g) was added dropwise under ice-cooling and stirring to a 
tetrahydrofuran (20 ml) solution of 
2-(4-trifluoromethoxyphenoxy)ethylamine (1.10 g) and triethylamine (0.51 
g) and the mixture was further stirred at room temperature for one hour. 
After completion of the reaction, the formed triethylamine hydrochloride 
was removed by filtration, and the solvent was removed under reduced 
pressure. 
The resulting residue was purified by silica gel chromatography (Wako gel 
C-200, eluted by toluene:ethyl acetate=9:1) to obtain 1.67 g of the title 
compound as colorless crystal. 
.sup.1 H-NMR (CDCl.sub.3, .delta. ppm) 
3.79 to 4.18 (4H, m), 6.15 to 6.31 (1H, br), 6.80 to 7.76 (8H, m) 
(7) Synthesis of 
N-[2-(4-difluoromethoxyphenoxy)ethyl]-2,6-difluorobenzamide (Compound 
(1-35)) 
To a mixed solution of dichloromethane (30 ml) and water (10 ml) were added 
N-[2-(4-hydroxyphenoxy)ethyl]-2,6-difluorobenzamide (1.16 g), potassium 
hydroxide (1.10 g) and tetrabutylammonium bromide (0.10 g), then 
chlorodifluoromethane (3.50 g) was slowly blown therein at room 
temperature under stirring, and the mixture was further stirred at room 
temperature for one hour. 
After completion of the reaction, dichloromethane was added to the reaction 
mixture to extract the title compound. The organic layer was washed with a 
saturated saline solution and dried over anhydrous sodium sulfate, and 
then the solvent was removed under reduced pressure. 
The resulting residue was purified by silica gel chromatography (wako gel 
C-200, eluted by toluene:ethyl acetate=9:1) to obtain 0.87 g of the title 
compound as colorless crystal. 
.sup.1 H-NMR (CDCl.sub.3, .delta. ppm) 
3.78 to 4.20 (4H, m), 6.42 (1H, t, J=74.2), 6.28 to 6.51 (1H, br), 6.71 to 
7.44 (7H, m) 
(8) Synthesis of 
N-{2-[4-(2-chloro-1,1,2-trifluoroethoxy)-phenoxy]ethyl}-2,6-difluorobenzam 
ide (Compound (1-38)) 
A tetrahydrofuran (5 ml) solution of 2,6-difluorobenzoyl chloride (0.71 g) 
was added dropwise under ice-cooling and stirring to a tetrahydrofuran (20 
ml) solution of 2-[4-(2-chloro-1,1,2-trifluoroethoxy)phenoxy]ethylamine 
(1.08 g) and triethylamine (0.40 g) and the mixture was further stirred at 
room temperature for one hour. 
After completion of the reaction, the formed triethylamine hydrochloride 
was removed by filtration, and the solvent was removed under reduced 
pressure. 
The resulting residue was purified by silica gel chromatography (Wako gel 
C-200, eluted by toluene:ethyl acetate=9:1) to obtain 1.76 g of the title 
compound as colorless crystal. 
.sup.1 H-NMR (CDCl.sub.3, .delta. ppm) 
3.77 to 4.21 (4H, m), 6.14 to 6.35 (1H, m), 6.53 to 6.73 (1H, br), 6.73 to 
7.44 (7H, m) 
(9) Synthesis of 
N-{2-[4-(2,2,2-trifluoroethoxy)phenoxy]ethyl}-2,6-difluorobenzamide 
(Compound (1-40)) 
A tetrahydrofuran (5 ml) solution of 2,6-difluorobenzoyl chloride (0.70 g) 
was added dropwise under ice-cooling and stirring to a tetrahydrofuran (20 
ml) solution of 2-[4-(2,2,2-trifluoroethoxy)phenoxy]ethylamine (0.94 g) 
and triethylamine (0.40 g) and the mixture was further stirred at room 
temperature for one hour. 
After completion of the reaction, the formed triethylamine hydrochloride 
was removed by filtration, and the solvent was removed under reduced 
pressure. 
The resulting residue was purified by silica gel chromatography (Wako gel 
C-200, eluted by toluene:ethyl acetate=9:1) to obtain 1.18 g of the title 
compound as colorless crystal. 
.sup.1 H-NMR (CDCl.sub.3, .delta. ppm) 
3.80 to 4.40 (6H, m), 6.28 to 6.53 (1H, br), 6.72 to 7.44 (1H, m) 
(10) Synthesis of 
N-[3-(4-trifluoromethoxyphenoxy)propyl]-2,6-difluorobenzamide (Compound 
(1-43)) 
A tetrahydrofuran (5 ml) solution of 2,6-difluorobenzoyl chloride (0.88 g) 
was added dropwise under ice-cooling and stirring to a tetrahydrofuran (20 
ml) solution of 3-(4-trifluoromethoxyphenoxy)propylamine (1.18 g) and 
triethylamine (0.50 g) and the mixture was further stirred at room 
temperature for one hour. 
After completion of the reaction, the formed triethylamine hydrochloride 
was removed by filtration, and the solvent was removed under reduced 
pressure. 
The resulting residue was purified by silica gel chromatography (Wako gel 
C-200, eluted by toluene:ethyl acetate=9:1) to obtain 1.38 g of the title 
compound as colorless crystal. 
.sup.1 H-NMR (CDCl.sub.3, .delta. ppm) 
2.03 to 2.21 (4H, m), 3.57 to 4.14 (4H, m), 6.19 to 6.38 (1H, br), 6.74 to 
7.43 (7H, m) 
(11) Synthesis of 
N-[2-(4-trifluoromethoxyphenoxy)ethyl]-2,6-difluorobenzthioamide (Compound 
(1-2)) 
Lawesson's reagent (1.94 g) was added to a toluene (20 ml) solution of 
N-[2-(4-trifluoromethoxyphenoxy)ethyl]-2,6-difluorobenzamide (1.44 g) and 
the mixture was stirred at room temperature for 3 hours. 
After completion of the reaction, the solvent was removed under reduced 
pressure. 
The resulting residue was purified by silica gel chromatography (Wako gel 
C-200, eluted by toluene:ethyl acetate=20:1) to obtain 1.56 g of the title 
compound as a pale yellowish crystal. 
.sup.1 H-NMR (CDCl.sub.3, .delta. ppm) 
4.20 to 4.37 (4H, m), 6.79 to 7.38 (7H, m), 7.71 to 7.89 (1H, br) 
(12) Synthesis of other Compound (1) in Table 3 
In accordance with the methods described in the above-mentioned (1) to 
(11), the other Compounds (1) in Table 3 was synthesized. 
The thus synthesized (1) to (11) as mentioned above and physical properties 
thereof are shown in Table 3. 
TABLE 3 
__________________________________________________________________________ 
1 STR30## 
- 
Compound 
R.sup.1 
R.sup.2 
R.sup.3 
OC.sub.x H.sub.y F.sub.z Cl.sub.m 
A n Physical properties 
__________________________________________________________________________ 
1-1 H H H 4-OCF.sub.3 
O 2 m.p. 93.about.95.degree. C. 
1-2 F H H 4-OCF.sub.3 O 2 m.p. 57.about.58.de 
gree. C. 
1-3 Cl H H 4-OCF.sub.3 O 2 m.p. 68.about.70.de 
gree. C. 
1-4 Br H H 4-OCF.sub.3 O 2 m.p. 82.about.84.de 
gree. C. 
1-5 H H 3-F 4-OCF.sub.3 O 2 
1-6 H H 3-Cl 4-OCF.sub.3 O 2 
1-7 H H 4-F 4-OCF.sub.3 O 2 
1-8 H H 4-Cl 4-OCF.sub.3 O 2 m.p. 108.about.110. 
degree. C. 
1-9 H H 4-Br 4-OCF.sub.3 O 2 
1-10 F F H 4-OCF.sub.3 O 2 m.p. 79.about.81.de 
gree. C. 
1-11 F Cl H 4-OCF.sub.3 O 2 m.p. 104.about.105. 
degree. C. 
1-12 Cl Cl H 4-OCF.sub.3 O 2 m.p. 133.about.134. 
degree. C. 
1-13 F H 4-F 4-OCF.sub.3 O 2 m.p. 66.about.67.de 
gree. C. 
1-14 F F 4-F 4-OCF.sub.3 O 2 m.p. 113.about.114. 
degree. C. 
1-15 CH.sub.3 H H 4-OCF.sub.3 O 2 m.p. 56.about.58.d 
egree. C. 
1-16 CH.sub.3 O H H 4-OCF.sub.3 O 2 n.sub.D.sup.20 
1.5260 
1-17 CF.sub.3 H H 4-OCF.sub.3 O 2 m.p. 72.about.74.d 
egree. C. 
1-18 CHF.sub.2 O H H 4-OCF.sub.3 O 2 
1-19 CF.sub.3 O H H 4-OCF.sub.3 O 2 m.p. 69.about.70.degr 
ee. C. 
1-20 CF.sub.3 H H 4-OCF.sub.3 O 2 m.p. 108.about.110. 
degree. C. 
1-21 H H 3-CH.sub.3 4-OCF.sub.3 O 2 
1-22 H H 3-CH.sub.3 O 4-OCF.sub.3 O 2 
1-23 H H 3-CF.sub.3 4-OCF.sub.3 O 2 
1-24 H H 3-CF.sub.3 O 4-OCF.sub.3 O 2 
1-25 H H 4-CH.sub.3 4-OCF.sub.3 O 2 
1-26 H H 4-CH.sub.3 O 4-OCF.sub.3 O 2 
1-27 H H 4-CF.sub.3 4-OCF.sub.3 O 2 m.p. 101.about.104 
.degree. C. 
1-28 H H 4-CF.sub.3 O 4-OCF.sub.3 O 2 m.p. 74.about.76.deg 
ree. C. 
1-29 CN H H 4-OCF.sub.3 O 2 m.p. 95.about.98.de 
gree. C. 
1-30 NO.sub.2 H H 4-OCF.sub.3 O 2 m.p. 99.about.100. 
degree. C. 
1-31 H H 3-CN 4-OCF.sub.3 O 2 m.p. 76.about.77.de 
gree. C. 
1-32 H H 3-NO.sub.2 4-OCF.sub.3 O 2 
1-33 H H 4-CN 4-OCF.sub.3 O 2 
1-34 H H 4-NO.sub.2 4-OCF.sub.3 O 2 m.p. 123.about.125. 
degree. C. 
1-35 F F H 4-OCHF.sub.2 Q 2 m.p. 86.about.89.deg 
ree. C. 
1-36 F F H 4-OCF.sub.2 CFH.sub.2 O 2 
1-37 F F H 4-OCF.sub.2 CF.sub.2 H O 2 m.p. 
98.about.100.degree. C. 
1-38 F F H 4-OCF.sub.2 CFClH O 2 m.p. 82.about.84.d 
egree. C. 
1-39 F F H 4-OCF.sub.2 CFHCF.sub.3 O 2 
1-40 F F H 4-OCH.sub.2 CF.sub.3 O 2 m.p.122.about 
.124.degree. C. 
1-41 F F H 2-OCF.sub.3 O 2 
1-42 F F H 3-OCF.sub.3 O 2 m.p. 65.about.67.de 
gree. C. 
1-43 F F H 4-OCF.sub.3 O 3 m.p. 108.about.109. 
degree. C. 
1-44 F F H 4-OCF.sub.3 O 5 
1-45 F F H 4-OCHF.sub.2 S 2 
1-46 F F H 4-OCF.sub.3 S 2 m.p. 64.about.65.de 
gree. C. 
1-47 F F H 4-OCF.sub.2 CFH.sub.2 S 2 
1-48 F F H 4-OCF.sub.2 CF.sub.2 H S 2 
1-49 F F H 4-OCF.sub.2 CFClH S 2 
1-50 F F H 4-OCF.sub.2 CFHCF.sub.3 S 2 
1-51 F F H 4-OCH.sub.2 CF.sub.3 S 2 
1-52 CH.sub.3 CH.sub.3 H 4-OCF.sub.3 O 2 m.p.122.about.123.d 
egree. C. 
1-53 CH.sub.3 O CH.sub.3 O H 4-OCF.sub.3 O 2 m.p.112.about.113.deg 
ree. C. 
1-54 CH.sub.3 Cl H 4-OCF.sub.3 O 2 
1-55 OH H H 4-OCF.sub.3 O 2 m.p.103.about.105.d 
egree. C. 
1-56 OH H 4-Cl 4-OCF.sub.3 O 2 m.p. 101.about.102.de 
gree. C. 
__________________________________________________________________________ 
(m.p.: melting point) 
Example 3 
(Preparation of Formulation) 
(1) Preparation of Granule 
Five parts by weight of Compound (1-1), 35 parts by weight of bentonite, 57 
parts by weight of talc, 1 part by weight of Neopelex powder (trade name, 
produced by Kao K.K.) and 2 parts by weight of sodium lignosulfonate were 
uniformly mixed, and then, the mixture was kneaded with addition of a 
small amount of water, followed by granulation and drying, to obtain a 
granule. 
(2) Preparation of Wettable Powder 
Ten parts by weight of Compound (1-1), 70 parts by weight of kaolin, 18 
parts by weight of white carbon, 1.5 parts by weight of Neopelex powder 
(trade name, produced by Kao K.K.) and 0.5 part by weight of Demol (trade 
name, produced by Kao K.K.) were uniformly mixed, and then the mixture was 
pulverized to obtain a wettable powder. 
(3) Preparation of Emulsifiable Concentrate 
Twenty parts by weight of Compound (1-1), 70 parts by weight of xylene by 
adding 10 parts by weight of Toxanone (trade name, produced by Sanyo Kasei 
Kogyo) were uniformly mixed, and dissolved therein to obtain an 
emulsifiable concentrate. 
(4) Preparation of Dustable Powder 
Five parts by weight of Compound (1-1), 50 parts by weight of talc and 45 
parts by weight of kaolin were uniformly mixed to obtain a dustable 
powder. 
Example 4 
(Tests of Effects) 
(1) Test of Effect on Southern Root-knot Nematode 
The respective wettable powders of the compounds (1) shown in Table 3 
prepared in accordance with Example 3 were diluted to 300 ppm with water 
and 0.1 ml thereof was placed in a test tube, and 0.9 ml of an aqueous 
solution containing about 500 southern root-knot nematodes was placed 
therein (final concentration: 30 ppm). 
Next, these test tubes were left to stand in a thermostat chamber at 
25.degree. C., and after 2 days, nematocidal rate was determined by 
observing with a microscope. 
The nematocidal effect was evaluated by using 4 ranks of A to D depending 
on the range of nematocidal rate (A: 100%, B: less than 100 to 80%, C: 
less than 80 to 60% and D: less than 60%). These results are shown in 
Table 4. 
TABLE 4 
______________________________________ 
Test of effect on southern root-knot nematode 
Compound Effect 
______________________________________ 
1-2 A 
1-3 A 
1-10 A 
1-14 A 
1-15 A 
1-16 A 
1-17 A 
1-30 A 
1-35 A 
1-37 A 
1-38 A 
1-40 A 
1-43 A 
1-46 A 
______________________________________ 
(2) Test of Effect on Two-spotted Spider Mite Egg 
The respective wettable powders of the compounds (1) shown in Table 3 
prepared in accordance with Example 3 were diluted to 300 ppm with water 
containing a surfactant (0.01%), and in these respective chemical 
solutions, kidney bean leaves (diameter: 20 mm) on which 15 two-spotted 
spider mite female adults were infested for 24 hours to lay eggs and then 
eliminated were dipped for 10 seconds, respectively. 
Next, test tubes in which each of these leaves were placed were left to 
stand in a thermostat chamber at 25.degree. C., and after 6 days, egg 
killing rate was determined by counting unhatched larvae in the respective 
leaves. 
The evaluation of the egg killing effect was shown by 4 ranks of A to D 
depending on the range of egg killing rate (A: 100%, B: less than 100 to 
80%, C: less than 80 to 60% and D: less than 60%). 
These results of evaluating these egg killing effects are shown in Table 5. 
TABLE 5 
______________________________________ 
Test of effect on two-spotted spider mite egg 
Compound Effect 
______________________________________ 
1-2 A 
1-4 A 
1-13 A 
1-19 A 
1-30 A 
1-35 A 
1-46 A 
______________________________________ 
(3) Test of controlling effect on rice blast (preventive effect) 
In plastic flowerpots having a diameter of 6 cm, 10 rices (seedlings 
variety: Nihonbare) were grown per one flowerpot, and to the young plants 
at 1.5 leaf stage, the chemicals obtained by diluting the wettable powder 
of the compounds (1) shown in Table 3 prepared in accordance with Example 
3 to 500 ppm with water containing a surfactant (0.01%) were sprayed in an 
amount of 20 ml per one flowerpot, respectively. 
After spraying, the rice seedlings were grown in a glass greenhouse for 2 
days, and then a suspension of conidiospores of rice blast collected from 
infected leaves was sprayed uniformly to the plant leaves to be inoculated 
thereinto. 
After inoculation, the rice seedlings were grown in a moist chamber at 
28.degree. C. for 5 days, and the degree of lesion of rice blast appeared 
on the leaves was examined. 
The fungicidal effect was evaluated by using 6 ranks of 0 to 5 as compared 
with the degree of lesion in the non-treated control (0: all area is 
infected, 1: lesion area is about 60%, 2: lesion area is about 40%, 3: 
lesion area is about 20%, 4: lesion area is 10% or less and 5: no lesion 
is observed). 
The results are shown in Table 6. 
TABLE 6 
______________________________________ 
Test of controlling effect on rice blast 
(preventive effect) 
Compound Effects 
______________________________________ 
1-1 3 
1-2 1 
1-8 4 
1-10 1 
1-13 1 
1-19 2 
1-46 2 
1-55 2 
1-56 4 
Non-treated 0 
district 
______________________________________ 
(4) Test of controlling effect on wheat brown rust (preventive effect) 
In plastic flowerpots having a diameter of 6 cm, 10 wheat seedlings 
(variety: Kobushi Komugi) were grown per one flowerpot, and to the young 
plants at 1.5 leaf stage, the chemicals obtained by diluting the wettable 
powders of the compounds (1) shown in Table 3 prepared in accordance with 
Example 3 to 500 ppm with water containing a surfactant (0.01%) were 
sprayed in an amount of 20 ml per one flowerpot, respectively. 
After spraying, the wheat seedlings were grown in a glass greenhouse for 2 
days, and then a suspension of spores of wheat brown rust 
(3.times.10.sup.5 spores/ml) was sprayed uniformly to the plants to be 
inoculated thereinto. 
After inoculation, the wheat seedlings were grown in a glass greenhouse for 
one week, and the degree of lesion of wheat brown rust appeared on the 
first leaves was examined. 
The results are shown in Table 7 according to the 6 rank evaluation method 
described in the above (3). 
TABLE 7 
______________________________________ 
Test of controlling effect on wheat brown 
rust (preventive effect) 
Compound Effects 
______________________________________ 
1-1 4 
1-2 3 
1-8 3 
1-10 1 
1-13 1 
1-19 2 
1-30 3 
1-46 1 
1-52 2 
1-53 4 
1-55 3 
1-56 2 
Non-treated 0 
district 
______________________________________ 
Utilizability in Industry 
The novel N-[(fluoroalkoxy)phenoxyalkyl]benzamide derivative of the present 
invention has excellent effects of nematocidal, acaricidal, fungicidal, 
etc.