CA2296123A1

CA2296123A1 - Pyrazole compounds, and their production and use

Info

Publication number: CA2296123A1
Application number: CA002296123A
Authority: CA
Inventors: Makoto Hatakoshi; Akira Shuto; Sumio Nishida; Hirosi Kisida
Original assignee: Individual
Current assignee: Sumitomo Chemical Co Ltd
Priority date: 1988-12-27
Filing date: 1989-12-18
Publication date: 1990-06-27
Also published as: CA2296121A1

Abstract

The present invention is directed to a pyrazole compound of the formula:
wherein R1 is a C1-C8 alkyl group, a C2-C8 alkenyl group or a C3-C8 alkynyl group, these groups being unsubstituted or substituted with halogen, hydroxy and/or C1-C6 alkoxy, or a group of the formula:
wherein R5 is a hydrogen atom, a halogen atom, a hydroxy group, a cyano group, a nitro group, a C1-C4 alkyl group, a halo (C1-C4) alkyl group, a C1-C4 alkoxy group, a halo (C1-C4) alkoxy group, a C1-C4 alkylthio group, a halo (C1-C4) alkylthio group, a C2-C4 alkenyl group, a C2-C4 alkynyl group, a C2-C4 alkenyloxy group, a C2-C4 alkynyloxy group, a C2-C4 alkenylthio group, a C2-C4 alkynylthio group, a halo (C2-C4) alkenyl group, a halo (C2-C4) alkynyl group, a halo (C2-C4) alkenyloxy group, a halo (C2-C4) alkynyloxy group or a halo(C2-C4)alkenylthio group and n is an integer of 1 to 5;
R2 and R3 are the same or different and each represent a hydrogen atom, a halogen atom or a C1-C3 alkyl group; R4 is a hydrogen atom, a halogen atom, a C1-C4 alkyl group or a halo(C1-C4)alkyl group; A is either one of the formulae:
wherein R6, R7, R8 and R9 are the same or different and each represent a hydrogen atom, a halogen atom or a C1-C3 alkyl group, X is an oxygen atom, a sulfur atom, a methylene group, a carbonyl group, a sulfoxide group, a sulfonyl group or a single bond when R1 is the group of the formula:
wherein R5 and n are each as defined above; or a group of the formula:

Description

PYRAZOLE COMPOUNDS, AND THEIR PRODUCTION AND USE
This application is divided out of Canadian Patent Application Serial No. 2,005,786 filed December 18, 199.
The present invention relates to pyrazole compounds, their production and use.
Organophosphorus insecticides, organochlorinated insecticides, carbamate insecticides, etc. have made a great contribution to the prevention and extermination of pests.
Some of these insecticides, however, are highly toxic.
Further, their residual effect causes sometimes unfavorable abnormality in the ecosystem of living things. Furthermore, resistance to those insecticides has been noticed in house flies, planthoppers, leafhoppers, rice borers, etc.
As a pesticide having a juvenile hormone-like activity, there is known "methoprene" (U. S. patent 3,904,662). Further, Canadian patent 1,231,945 and EP-A1-0287959 disclose certain compounds having a juvenile hormone-like activity. However, the pesticidal acvitity of those compounds is not always satisfactory.
As a result of extensive study, it has now been found that some pyrazole compounds exert a noticeable juvenile hormone-like activity and produce a remarkable pesticidal effect against pests belonging to Diptera, , Hemiptera, Coleoptera, Lepidoptera, Orthoptera, Blattaria, Thysanoptera, Siphonaptera, Isoptera, etc. in agricultural fields, forest lands, granaries, stored products, sanitary facilities, etc. at low concentrations. This invention is based on the above finding.
The pyrazole compounds of the invention are represented by the formula:
N
R1-A-CH --~-CH -~-~-N ' ( R4 ) m wherein R1 is a C1-Cg alkyl group, a C2-Ce alkenyl group or a C3-CB alkynyl group, these groups being unsubstituted or substituted with halogen, hydroxy and/or C1-C6 alkoxy, or a group of the formula:
( R5 ) n wherein RS is a hydrogen atom, a halogen atom, a hydroxy group, a cyano group, a nitro group, a C1-C4 alkyl group, a halo (C1-C4) alkyl group, a C1-C4 alkoxy group, a halo (Cl-C4) alkoxy group, a Cl-C4 alkylthio group, a halo (Cl-C4) alkylthio group, a C2-C4 alkenyl group, a C2-Cg alkynyl group, a C2-C4 alkenyloxy group, a C2-C4 alkynyloxy group, a C2-C4 alkenylthio group, a Ca-C4 alkynylthio group, a halo (Cz-C4) alkenyl group, a halo (C2-C4) alkynyl group, a halo (CZ-C4) alkenyloxy group, a halo (Cz-C4) alkynyloxy group or a halo (CZ-C4) alkenylthio group and n is an integer of 1 to 5;
R2 and R3 are the same or different and each represent a hydrogen atom, a halogen atom or a C1-C3 alkyl group; R' is a hydrogen atom, a halogen atom, a C1-Cq alkyl group or a halo (C1-C4) alkyl group; A is either one of the formulae -X-CHZ-CH-CHZ-CH=C- or -X-CHZ-CH-CHZ-CHz-CH-R6 R' Ra R9 wherein R6, R', Re and R9 are the same or different and each represent a hydrogen atom, a halogen atom or a Cl-C3 alkyl group, X is an oxygen atom, a sulfur atom, a methylene group, a carbonyl group, a sulfoxide group, a sulfonyl group or a single bond when R1 is the group of the formula:
Y-CH-~m iRio) wherein RS and n are each as defined above; or a group of the formula:
~ R5 ) n wherein Rl° and Rll are the same or different and each represent a hydrogen atom, a halogen atom or a Cl-C3 alkyl group, X is an oxygen atom, a sulfur atom, a methylene group, a carbonyl group, a sulfoxide group, a sulfonyl group or a single bond, Y is an oxygen atom, a sulfur atom or a methylene group and p is an integer of 1 to 4 when RI is a C1-C8 alkyl group, a CZ-Ce alkenyl group or a C3-Cg alkynyl group, these groups being unsubstituted or substituted with halogen, hydroxy and/or C1-C6 alkoxy; Q is an integer of 0 to 2; and m is an integer of 1 to 3.
The pyrazole compound (I) can be produced, for instance, by reacting a compound of the formula:
Rl -A- i ~I --~- i H -i~-B i I I ) - 3a -wherein Rl, R2, R3, A and Q are each as defined above and B
is a halogen atom, a mesyloxy group or a tosyloxy group with a compound of the formula:
w H~ (R4) (III) m wherein R4 and m are each as defined above in the presence of an acid-eliminating agent.
The above reaction may be carried out in the presence or absence of an inert solvent, of which preferred examples are dimethylformamide, dimethylsulfoxide, tetra-hydrofuran, toluene, dimethoxyethane, dimethylacetamide, etc. As the acid-eliminating agent, there may be employed an alkali metal, an alkali metal hydride, an alkali metal amide, an alkali metal hydroxide, an alkali metal carbonate, an organic base (e.g. 4-dimethylaminopyridine), etc. For acceleration of the reaction, a phase transfer catalyst, e.g.
benzyltriethylammonium chloride, tetra-n-butylammonium bromide or tris(3,6-dicxaheptyl)amine,may be present in the reaction. In this instance, water can be used as the reaction medium.
The reaction is normally achieved at a temperature of about -30°C to 200°C, preferably of about 0°C to 110°C, for a period of about 0.5 to 30 hours. The molar ratio of the compounds (II) and (III) is usually about 1 . 0.1 - 10 moles, preferably about 1 . 0.8 - 1.2 moles.
Upon completion of the reaction, the reaction mixture is subjected to ordinary post treatment , for example, extraction with an organic solvent and concentration. When desired, purification by chromatography, distillation, re-crystallization or the like may be carried out.
The pyrazole compounds (I) of the invention include optical isomers and geometrical isomers with respect to R2, R3, R6, R~, R8, R9 and/or R11. All of these isomers are included within the scope of the invention.
Representative examples of the pyrazole compounds (I) obtainable by the above procedure are shown in Table 1.

x N
x x x x a x M

x M N f 1 N N N

() -IY, x N N x x x U U U U U U

U

H U t~ U U-U U-f~ U U

I

I x x x x x N U U U U U
x I 1 i 1 I
U O O O O O

O / i / / i / \ ~ w ~ \ ~ w ~ w O O O O O
~o~ 1 I I I I
.1x M
U-x -f x N
U-fx I I
r-1 ~' 1 N
Ia I N ~
H x N
E A4 V / / V , I
M ~ ~ 1 ~ x H x x ~ ~ _N \ U

M 1 II!
x ~ x U U U

M M

w x x v x U x ac x x r, a .r, a V

N
x U

x ''' I N x x ~ x V - p~, N x U U
V '~'., N N IN IN IN IN IN
x N ,?'., N x x x x x x x U-fxU-UUU UU UUU
I I I 1 1 I 1 t I
I

x U

x U
t N N x N 1 cr1 N N N
U U I~ M U U-U U U U
p p U-U O O O O O

i i ' ~' i I i ~ ( ~ ~ x ~ ~ w \ \ \
O O V O O O O O
I s 1 1 1 I 1 1 N
x i / i i /
U
U-U
c~
x U

N

C~ M M

x x ~ x x x a U

x v a t '~

a >~ M

.,., a U

1 I 1 t t N ( I c~1 N N N N
U x U-U U U U U

N I M N N N N N
U U-U U U U U U

I
t I t I 1 1 I
U U U U V U U U
I t I t I I I
O O O O O O O
a ~ I ~ I ~~ ~ I ~ I ~ 1 \ \ \ \ \ w \
O O O O O O O
I ~ 1 ~ ~ ~ I ~ ~ ~ I
I \ ~ \ \ \ \ \

x x x x x ~d--a~

s~

.r., U

U ~ U U U U

N N N N N
x N x x x x x I

N N CV N N
x x x x x U U U V U

O O ~-t O ~ O r1 O
U U U
a \ I ~ ~ \ I I

i r., ~ \ \ I
x i i U
w x w x x x x x b v a _a a U

of ! 1 I 1 x _'-, ''' x x x U U U ' U
x N x xN x x x ! 1 1 I 1 I

o~
I
1 ! I 1 1 N N N N CJ
U U U U U
r1 O O O O O
U
I ~ I
O O O O O
w w ..-r I ~ I ' I \ I \ I
w o w w w w w x E
x x x x x b a~
a a U
o,!

M N N N N N
U- x x x x x x U U U U U
N N N N N
V ~ U U U U U
( 1 1 I 1 1 r-1 I i I 1 1 CV N N N N
O O O O O
,.
O O O O O
\I
U
~v x M U r1 Z Z O x U

x w x x x b v a .~, U

V ~ U U
1 1 I i I
N N N N N
U ~ U U U U U

I

N N N N N
x x x x x U V U U V

O O O O O
~ ~ ( i~
\ ~ \
O O O O O

/ ~ w / ~ / / i \ I ~ ~ ~ \ ~ ~ I
w w w w x x x x x b x v a s;

U

I l I I I

x f'~7N N N N N

U -oc x x x x x U U U U U

N N N N N

x N x x x x x U- c>: U U U U U

I 1 1 I l I

I
N
r~1 i I 1 l I I
N N N N N
x x x x x U U U U U

O O O O O

a ' I ' t ' I ~ i ' 1 ,~ ~ I ~ I ~ I ~ I ~ l x U
-i ~ ~-I r, x w U U v w U

x x x x x x x a~
a a U
I i i 1 1 1 x c1 N N N N N N
U U U U U U
1 I 1 1 i I
x N x x x x ~ x t M

1 1 I t 1 1 N N N N N N
x x x x x x U U U V U U
1 ~ I 1 1 1 O O O O O O
\ ~ W ~ \ ~ \ I \ ~ \ I
O O O O O O
t 1 1 1 1 1 i M ~ I i x o \ I ~ I ~ I x x / I
\ \
x U cn N U N III M
r, x U x v x U x U

x x x x x b x >~
.,., U

U fx x x x x x N x x x x x U -c~ U U U U U

I
I

N N ( 1 1 x x N N N
U V U U U

O O O
/ I / ~ ~ I
\ \ ~ \ \
O O O O O
t 1 1 1 1 /
GG ~ x ~ / /
U w I \ L \ I
U ~; Gr fir G4 W

x x x x x. x ro a a U

x M 1 N N N
N x x x x 1 U U U 1 I 1~ N N N N N

x N x x x ac x x x U- tx V - U U U U U U

I
u~
I

N
I I x I
1 c.t N U N
N 1 M x x I x U U O U
01 O O ~ O
~ I ~ I ~ I ~ t \ ~
\ \ \ \ N \
x O O N U=O U O
I 1 t 1 1 1 ov P4 / I / I / ~ / I \ ( U
\ \ \ \ 1 w w w w x x x x x x b x a~
.ri U
I I I I

x cV1 N N N N

x x x x U U U U

I I

N N N N N N

N U U

I V p', U U U U 1 1 I I I t I

N
I 1 1 I I x x x x x x U U U U U O

O O O O O
N
x O O O O O U
/ / t / ~) /
N
x o cn x cn I x N N U N ~." N
N ~, W x x U-U
p4 .-. U U U U I
N N I'N II x a W w x U N
-- U U U x U

x x x x b x m --a U
~l U V U

N N N N

U W U U U U

1 1 i t 1 r r~

N
x 1 1 t V N N N
p U U U
O O U O U
r.C w ' / ~ / ~
N
V O O O

tIl ,.'~," N
I x U x v-a x x x ;' x U-U O-U-U /
N x x U U U

x x x x b x a~

a >~

v t 1 1 1 N N N N
U U U U
t 1 1 I
N N N N

t 1 1 1 1 ri N
IN IN IN U
U U U O
t 1 1 O O O / i w i i ~ i i I
N
r, x o a ~n=o o-~n=o a I
W w w w~

E;
x x x x x x o ,.
a .,., s~

U
1 t 1 1 t U- f~: x x x x x U U U U U

N N N N N
x N x x x x x o~
r~

t 1 N N N N
x x 1 x x U U N _U _V
1 1 x N N U 1 ~'1 1 n'1 x x t x x x x U U t» U-U V-U

a N N
x x V v I I 1 t t N
x 1 N1 U r1 N
x I x x U- U- V ~ U
x I x 1 x O U-U-U
N I
x o fir., Gsa W U x E

d: x x x x x x x a~

a a .r., >~

U

x ~ N N N N N N
U U U U U U

N N N N N N
U Is: U U U U U U

I

N

I
M
N

U N N
x x I rr1 U U
U-U ~ ~ O O

N N U U
x x U U O O O O

x x x N
a U U x I ~, I ~, I r., ~ U
.-, x x x x x x x I x I~ U-U U-U , , U-U U-U-U
I I
x x ~ ~ x x U U Gu W U U

x x x x x x rdx a~

.r., a U

t I I I 1 1 x M N N N N N N
U-x x x x x x x U U U U U U
N N N N N N
x N x x x x x x U-fx U U U U U U

I
N

N N N N
I x I x x x N U N U U U
x 1 x 1 s 1 U O U O O O

O \ ( ~ \ ( ~ ~ I
O ~ O O O

i N

N N N I

1 x x I x N

N U U N U x U x U _ ~ x x c~ 1 c~- WI
M x x 1 x U U U-U 1 x x x x -I II I II

M x x N M N

x N N x x x U U U U U U

x x x x x b x .'., >~

U

x lT1 N N N N N
U ~ U U U U U

N N N N N
x N x x x x x U-fx U U U U U

I
N
N
I
I 1 1 tr1 I
N N N 1 x N
x x x x N x V U U U-U U

O O O O O
I ~ ~ ~ I I
O O O O ~ O M
I I I 1 x 1 x I

N .-.

1 N ~ x N x U

x U

U M -- ~ x W-, I ~ x 1 x v x x C~4 U-V U- U- U '-' / U-U

il 1 t I i N c"~ c~1 ~ M

x :~: x x U U U U

x N

d: x x x x x U

b x I

c .r., a a t r I 1 x t'~1 N f'.t 1 I N N
U U x x U U

x N x x x ~1 x x x U- GG U U U-U U- W U U

I I t I I I 1 I
M
N
I

N N N N N
x r x x x x U N U U U U
1 x i I I 1 O U O O O O
;s, I
O
a ~ I ~ I ~ l ~ ~ ~ I.
o ~ 0 0 0 0 N N
x ., U N
1 x O U

-, x x r pt , U - U , / N
x w I ~ I .u-I w I
U U

M

W x x x U x U x x b p4 I I

r M c~1 a s~

s~

U

","' c'~ N I N N N
U-x x N x x x U U ~ U U 1 U
N 1 x N N N fy N
x N x x N x x - x x x i 1 I 1 I 1 I I 1 N

x U
II
x U

1 I 1 N ( I
N N N x N 1 Cr1 N
x x x U x x x x U U U 1 cn U U-U U
I 1 1 x x I 1 I
O O O U-U O O O
I
a / 1 / I ~ ~ N
\ ~ \ x ~ w w _U
O O O O O O
1 i 1 1 1 I 1 I

N
x N
N U x x 1 M U
U x x x U i i V-U / / V
x ~ ( ~ I x ~ ~ ~ ~ x U U U

x x x x x x x ro x a~

a a .r., a U

I 1 1 1 1 l I

x N N N N N N N
f1 U-x x x x x x x x U U U U U U V

N N N N N N N

x x x x x x x x N

U- U U U' U U U U

I I t I I I t I I

u~

N

x I I I I I i U
x x x x x x x U U U U U U U
O O O O O O IM
a ~ I ~ I ~ I ~ I ~ I ~ ( x w w \ ~ ~ ~ U

O O O O O O
I i i I
\ I
I \ I ti o ~ ( u~

x x x o N x U U .~ U a ~1 x x U rl c~ III U-U N U- U U-U U-U
U~ IIN U IIN U IIN I
x x ~t x x; x U U U U U U

x x x x x x b x v .~, a U

i I I 1 x N N N N N N
M

U U U U U U
~

U

N N N N N N

x N x x x x x x U-Ix U U U U U U

~o N
I

M
I x 1 U-U U-w I I 1 x x x x x U U U U U

M M O .-i O ~1 O
U U
N N N / , /
U U U

/ i / ~ / ~ i I i w ~ w U ~-~I ~1 G~ G~.~ U U

Practical and presently preferred embodiments for preparation of the pyrazole compounds (I) are illustratively shown in the following examples.
Example 1 To a mixture of anhydrous N,N-dimethylformamide (5 ml) and sodium hydride (60 % oil suspension; 39 mg), pyrazole (66 mg) was added, and the resultant mixture was stirred for 30 minutes. A solution of 3-(4-phenoxyphenoxy)-propyl bromide (300 mg) in anhydrous N,N-dimethylformamide (5. ml) was dropwise added thereto, followed by stirring at room.temperature for 5 hours. The reaction mixture was diluted with ethyl acetate (50 ml), washed with a saturated aqueous ammonium chloride solution twice , dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The oily substance thus obtained was subjected to column chromatography to give 246 mg of 1-[3-(4-phenoxy-23.5 phenoxy)propyl]pyrazole as a colorless oil. nD 1.5777.
Example 2 To a mixture of anhydrous dimethylsulfoxide (5 ml) and sodium hydride (60 % oil suspension'; 62 mg), pyrazole (106 mg) was added, and the resultant mixture was stirred for 30 minutes. A solution of 3-[4-(3-tolyloxy)phenoxy]-propyl bromide (500 mg) in anhydrous dimethylsulfoxide (5 ml) was dropwise added thereto, followed by stirring at room temperature for 3 hours. The reaction mixture was treated in the same manner as in Example 1 to give 34? mg of 1-~3-[4-(3-tolyloxy)phenoxy]propyl~pyrazole as a colorless oil.
n2~3.7 1.5738.

_ 28 In the same manner as above, there were prepared the pyrazole compounds (I), of which typical examples are shown in Table 2.

r~ U .~ w t~ o r1 ov n r n n u1 u1 u1 .-a o~
+J

U b .1 r1 . t~ u1 LW

ul v1 ?~ ~ Ll~ ~
O

,>~ nl C7 N O N O
O

W U s~ ~ ~ O

1~
x ac x x x N
x x ~ a U- W' 1 I 1 N N N
U U U
x N 1 I I I
U- Qi N N N N
I x x x x U U U U

I
N

N N N 1 c'1 U U U U- U
~~r~ 1 I 1 I
c>~ ~ O O O O
/ i / i f I ~ 1 \ ~ \ \
O O O O
1 1 i I
x M
U- lx N x N
u-x x w w w .Cl I
~a H x b I
r-1 N f~'1 O O O
U WZ

m ~ ~ ,-i u~ m C1 O O O~ N ~ 10 00 I~ t0 00 l0 (~

u1 ~1 ~ ~I1 u1 u1 u1 ;J

fd r-~ r~ r~ ri r) r-1 ri ,('"

U ~G

rl tf1 t"1 II1 u1 r1 r'1 N
~

' ?~ a' d' d' M ~ u1 sr O

N .!~ N D N O N O N (,a N Q N (.] N
O C.a ~ P~ 1~ s~
U

N

O

U M M n1 -- ~ x x ~I x U U U U

x x I I 1 -- x L4 M ~ ~ 1 M

x cn U 1 I I t 1 -Qi U U U

x U U U U

x N U I 1 1 I t 1 U-W' InI N N N N N N

I x x x x x x x x U-U U U U U U U

1 1 1 t I 1 1 M

1 1 1 1 t 1 1 N N N N N N N
x x x x x x x U U U U U U U

a o 0 0 0 0 0 0 I ~ ' ~ I i I ~ I ~ ~ ( I I 1 I t I I
! ~ ~ ~ I
w y y w w w I ~
0 0 0 ° '--' U L1 Z '-n .o ~ oo ai 00 v0 M N dD

M V' C1 O O1 t~ I~ I~ GO n wf uw n u1 w fd ri ri r~ rl r1 ~"., U
rd -.~ n tC1 GD c~ r1 +1 M M M M M

(U ~'., N (~ N O N (~ N Q N (a Q

a wU ~ a a ~ s~

a .',, U

x x x x x x x M

U-fY, 1 1 N N

U

U

x 1 1 1 1 1 N

U-(Y, N N N N N

1 x x x x x U U U U U

I
M

i 1 I I 1 N N N N N
x x x x x U U U U U

O O O O O
/ ~ / ~ / I / I / I
w ~ w W W
O O O O O
1 1 I t I
/ /
/ ~ ~ / i w I c.rr w I w I
x w w x w w w 1 ~ CV M C tW D
a r-'1 r~ rl ri e-I
Q Q Q

lI1 1I1 t0 C' rl N

r w ao o~ c~ r r r r r ~c r u1 u1 u1 u1 u1 u1 ,~ .
~

Uro ~rl Lf1 ri lf1 f'~1 t11 M
i-~

fn f0 : ~ ;

ro?, , d a ~ c W

N O N Q N A N Q N O N
O

Pa G ~ ~ ~
U

.,i O

U

x x x x x x x x M

x x x x ac x U U U U U U

x 1 1 1 1 1 I
N

U-pl, N N N N N N

U U

U U U U

I
N
M

N N N N N N
x x x ac x x U U U U U U

O O O O O O
i I i ( i I i ~ i 1 i I
O O O O O O

i i w f~ / I \ I
~1 M x W U U U W U
b 00 0, o .-a N
O O O ~ '~ r"~ N N N
U C:. Z

ov a~ m vo 0 v~ w o .-~ ow n m N

.

~d U
r0 -.~i o o ~r o w t1 ~

N .
N

V' er f'7 e1' M ch O N Q N (a N (a N Q N ~.] N
Q

a W ~ >~
U

.r.l O

U

_.

x x x x x x x x M

N N N N N N

U U U

U U U

x I I I I I I
N

U--~a N N N N N N

I x x ac x x x U U U U U U

I
M
cal I
i 1 1 I 1 1 N N N N N N
x x x x x x U U V U U U

O O O O O O
L, / I / I / I ~ I / I ~ !
w w ~ w w w O O O O O O
I t 1 1 1 I
/

N
i ~. x O /
i>~ ~ x '~' ~ x x I
O U ~ U U
N / U IIN j 1 r~'1 U ~ ( x U x U
'd a rn d- m .D c~ o0 O O O N N N N, 'F3 N
U Ql~r vo ~C1 r-1 1D N

m o ao 00 0 u~ u1 u1 u r"1 .
,y~

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On the application of the pyrazole compound (I) as a pesticide, it may be used as such or in an appropriate preparation form, e.g, an oil spray, an emulsifiable concentrate, a wettable powder, granules, a dust, an aerosol, a fogging agent, a toxic bait, etc. In those preparations, the pyrazole compound (I) is usually contained in about 0.1 to about 99.9 $ by weight, preferably in about 2 to about 80 $ by weight.
Such preparations can be formulated in peg, se conventional manners by mixing at least one of the pyrazole compounds (I) with an appropriate solid, liquid or gaseous carriers) or diluent(s) or a bait. An appropriate adjuvant(s), e.g. a surfactant, an adherent, a dispersant or a stabilizer may also be mixed therein to improve the dispersibility and other properties of the preparation.
Examples of the solid carriers or diluents are fine powders or granules of clays (e. g. kaolin clay, diatomaceous earth, synthetic hydrated silica, bentonite, fubasami clay, terra alba), tales, ceramics, other inorganic minerals (e. g. sericite, quartz, sulfur, active carbon, calcium carbonate, hydrated silica), chemical fertilizers (e. g. ammonium sulfate, ammonium phosphate, ammonium nitrate, urea, ammonium chloride), etc. Examples of the liquid carriers or diluents are water, alcohols (e. g.
methanol, ethanol), ketones (e. g. acetone, methylethyl-ketone), aromatic hydrocarbons (e. g. benzene, toluene, xylene, ethylbenzene, methylnaphthalene), aliphatic hydro-carbons (e. g. hexane, cyciohexane, kerosene, light oil), esters (e. g. ethyl acetate, butyl acetate), nitriles (e. g.
acetonitrile, isobutyronitrile), ethers (e. g. diisopropyl ether, dioxane), acid amides (e. g. N,N-dimethylformamide, N,N-dimethylacetamide), halogenated hydrocarbons (e. g.
dichloromethane, trichloroethane, carbon tetrachloride), dimethylsulfoxide, botanical oils (e. g. soybean oil, cotton-seed oil), etc. Examples of the gaseous carriers or xa~
diluents are Freon gas, butane gas, LPG (liquefied petroleum gas), dimethyl ether, carbon dioxide, etc.
fihe surfactants suitable for emulsification, dis-persion or spreading may be any of the ionic and non-ionic types. Their examples include alkylsulfates, alkylaryl-sulfonates, dialkylsulfosuccinates, polyoxyethylenealkyl-arylphosphates, condensates of naphthalenesulfonic acid and formalin, polyoxyethylene alkyl ethers, polyoxyethylene polyoxypropylene block copolymers, sorbitan fatty acid esters, polyoxyethylene sorbitan fatty acid esters, etc.
Examples of the adherents or dispersants may include casein, gelatin, polyvalent alcohols (e.g. starch powder, gum arabic, cellulose derivatives, alginic acid), lignin derivatives, bentonite, saccharides, synthetic water-soluble high molecular compounds (e. g. polyvinyl alcohol, polyvinyl-pyrrolidone, polyacrylic acid), etc. As the stabilizers, there may be used alkyl phosphates (e. g. PAP (isopropyl acid phosphate), BHT (2,6-di-tert-butyl-4-methyl-phenol), BHA
(a mixture of 2-tert-butyl-4-methoxyphenol and 3-tert-butyl-4-methoxyphenol), botanical oils, mineral oils, surfactants, aliphatic acids or esters, etc.

The base for toxic baits may comprise foou (e. g.
grain powders, essential oils, sugar, crystalline cellu-lose), an antioxidant (e. g. dibutylhydroxytoluene, butyl-hydroxyanisole, nordihydroguaiaretic acid), a preservative (e.g. dehydroacetic acid), a mis-feed inhibitor (e.g. red pepper powders), a flavoring agent (e. g. cheese flavor, onion flavor), etc.
The composition thus formulated may be applied as such or in a form diluted with water. In addition, said composition may contain other insecticides, nematocides, acaricides, fungicides, herbicides, plant growth regulators, synergistic agents, fertilizers, soil improvers, etc.
Particularly when employed in conjunction with conventional insecticides, a broad sgectrum of activity or a more immediate effect on very heterogeneous populations is provided. Examples of the insecticides include organic phosphorus compounds (e.g. fenitrothion (O,O-dimethyl-O-(3-methyl-4-nitrophenyl)phosphorothioate), malathion (S-[1,2-bis(ethoxycarbonyl)ethyl] O,O-dimethylphosphorothio-ate), dimethoate (O,O-dimethyl-S-(N-methylcarbamoylmethyl)-phosphorodithioate), salithion (2-methoxy-4H-1,3,2-benzo-dioxaphosphorin-2-sulfide), diazinon (O,O-diethyl-O-(2-isopropyl-6-methyl-4-pyrimidinyl)phosphorothioate), trichlorfon (2,2,2-trichloro-1-hydroxyethyl-0,0-dimethylphosphonate), dichlorvos (0-(2,2-dichlorovinyl)-O,O-dimethylphosphate), etc.), carbamate compounds (e. g. MPMC (3,4-dimethylphenyl N-methylcarbamate), MTMC (m-tolyl N-methylcarbamate), BPMC
(2-sec-butylphenyl N-methylcarbamate), carbaryl (1-naphthyl N-methylcarbamate), etc.) and pyrethroid compounds (e. g.
permethrin (3-phenoxybenzyl-d.~-cis,trans-3-(2,2-dichloro-vinyl)-2,2-dimethylcyclopropanecarboxylate), fenvalerate (a-cyano-m-phenoxybenzyl a-isopropyl-p-chlorophenylacetate), etc . ) .
The composition may be applied to pests using a conventional method, of which typical examples include spreading, fuming, soil treatment, incorporation into food for domestic animals or poultry, etc. It is further noticeable that addition of the composition to sericiculture food may lead to an increase of cocoons in number or thickening the cocoon layer.
The dosage of the pyrazole compound (I) as the active ingredient in an agricultural pesticidal composition is generally from about 5 to about 500 grams per 10 ares.
When the composition is applied as an emulsifiable concen-trate or a wettable powder, the concentration of the active ingredient is normally from about I to about 500 ppm. In the case of such formulations granules, fine granules and dusts, the composition may be applied as such without dilution with water. As a sanitary pesticidal composition, the composition in the form of an emulsifiable concentrate, an emulsifiable concentrate or a wettable powder may be diluted with water in a concentration of the active in-gredient being generally from about 1 to about 500 ppm and applied. In the case of a formulation such as an oil spray, an aerosol, a fumigant, a bait or the like, it may be applied as such.

Said amounts and concentrations are not definite and may vary depending on the type of preparation, application season, locus to be applied, mode of application, species of pests, degree of damage, etc.
Some practical embodiments of the composition according to the invention are illustratively shown in the following Formulation Examples wherein % and parts) are by weight and the compound numbers correspond to those in Table 2.
Formulation Example l One of Compounds Nos. 1 to 75 (20 parts), an emulsifier (a mixture of polyoxyethylene styrylphenyl ether, polymer of polyoxyethylene styrylphenyl ether and alkylaryl-sulfonate) (20 parts) and xylene (60 parts) were well mixed to make a 20% emulsifiable concentrate.
~ormulation.Example 2 One of Compound Nos. 1 to 75 (20 parts), an emulsifier (sodium Iaurylsulfate) (5 parts) and diatomaceous earth (#300 mesh; 75 parts) were well mixed in a pulverizer to make a 20% wettable powder.
Formulation Example 3 One of Compound Nos. 1 and 2 (3 parts), acetone (20 parts) and talc (#300 mesh: 97 parts) were well mixed in a pulverizer, followed by removal of acetone by evaporation to make a 3% dust.
Formulation Example 4 One of Compound Nos. 1 to 75 (5 parts), a dispersing agent (calcium ligninsulfonate) (2 parts) and clay (93 parts) were well mixed, followed by addition of a small amount of water. The resultant mixture was kneaded and granulated with the aid of a granulator and dried to make 5% granules.
Formulation Example 5 Compound No. 1 (2 parts), a dispersing agent (calcium ligninsulfonate) (2 parts) and clay .(96 parts) were well mixed, followed by addition of a small amount of water.
The resultant mixture was kneaded and granulated with the aid of a fine granulator and dried to make 2% fine granules.
Formulation Example 6 Compound No. 1 (0.2 part), xylene (2 parts), dimethylformamide (2 parts) and lamp oil (95.8 parts) were well mixed to make an oil spray.
Formulation Example 7 Compound No. 1 (0.05 part), tetramethrin (N-(3,4,5,6-tetrahydrophthalimido)methylchrysanthemate) (0.2 part), resmethrin (5-benzyl-3-furylmethyl (~)-cis,trans-chysanthemate) (0.05 part), xylene (7 parts) and deodorized lamp oil (42.7 parts) were well mixed and charged into an aerosol container. Upon attachment of a valve portion, a pressurizing agent (LPG) (50 parts) was charged through the valve to make an aerosol.
Formulation Example 8 Compound No. 1 (1 part) and sesame oil (3 parts) are mixed, and butyl hydroxyanisole (0.03 part), dehydroacetic acid (0.1 part), black sugar (10 parts), crystalline cellulose (30 parts) and potato starch (55.87 parts) were added thereto. The resultant mixture was uniformly mixed and pressurized with a load of 15 kg/cmZ to make a toxic bait in tablet form, each tablet having a weight of approx. 4 g and a diameter of 30 mm.
The following Test~Examples present some typical test data indicating the excellent pesticidal activity of the pyrazole compounds (I). The compounds used for comparison are shown in Table 3 below:
Table 3 Ca~ound No. Structure Remarks (A) CH3 CH3 CH3 Known as ~3p~ ~ ( I "methoprene" ;
C ( CH2 ) 3~2CH~~~ (~3 ) 2 U . S . patent ~3 3,904,662 (g) ~ Canadian / \ ~-~ (Cfi2) 3 ' 13 patent i 1,231,45;
C~ound No.

(C) / -\ / \ ~ ~-287959;
2 ~ ~1 Compound No.

~3 Test Example 1 An emulsifiable concentrate prepared according to Formulation Example 1 was diluted with water to make a 400 fold dilution. The dilution (0.7 ml) was added to 100 ml of distilled water. Last instar larvae of common mosquito (Culex pipiens pallens) were released therein and reared for 7 days until their emergence. The rate of emergence was observed with two replications. The results are shown in Table 4.

Table 4 Test compound Concentration Rate of emergence No. ~ (PPm~
1 ~ 3.5 ~ 0 2 3.5 , 0 3 3.5 ~ 0 4 3.5 0 5 3.5 0 ~

6 3.5 0 7 3.5 0 g 3.5 0 g 3.5 0 10 ~ 0 3.5 11 3.5 i 0 12 3.5 0 13 3.5 0 14 3.5 0 15 3.5 0 16 3.5 0 17 3.5 0 lg 3.5 0 19 3.5 0 20 3.5 0 21 3.5 0 22 3.5 0 23 3.5 0 24 3.5 0 25 3.5 0 26 3.5 0 27 3.5 0 28 3.5 0 29 3.5 0 30 3.5 0 31 3.5 0 32 3.5 0 33 3.5 0 34 3.5 0 35 3.5 0 36 3.5 0 37 3.5 0 3p 3.5 0 39 3.5 0 40 3.5 0 41 3.5 0 42 3.5 0 43 3.5 ~ 0 44 3.5 0 45 3.5 0 46 3.5 , 0 47 3.5 ' 0 48 3.5 0 (Continued) Test compound Concentration Rate of emergence No. (ppm) 49 3.5 0 50 3.5 0 51 3.5 0 52 3.5 0 53 3.5 0 54 3.5 0 55 3.5 0 56 3.5 0 57 3.5 0 58 3.5 0 59 3.5 0 60 3.5 0 61 3.5 0 62 3.5 0 63 3.5 0 64 3.5 0 65 3.5 0 66 3.5 0 67 3.5 0 68 3.5 0 69 3.5 0 70 3.5 0 7I 3.5 0 72 3.5 0 73 3.5 ~ 0 74 3.5 0 75 3.5 0 (A) 3.5 0 Untreated ' - ~ 90 Test Example 2 Powdered animal feed (2 g) was thoroughly mixed with bran (14 g). An emulsifiable concentrate prepared according to Formulation Example 1 was diluted with water to a 5pec#.f~ed ~ concentration, and the dilution was added to the above mixture. The resultant mixture was stirred well to make an artificial culture. Thirty housefly larvae (Musca domestics) were reared therein until their pupation.

The obtained pupae were glaced into a plastic cup, and the rate of emergence was determined. According to the follow-ing equation, the emergence inhibition (%) was calculated:
Emergence Rate of emergence in treated plot inhibition - (1 - Rate of emergence in untreated plot ) X i00 (%) The results are shown in Table 5.
Table 5 Test compound No. Emergence inhibition (%) 3 ppm 1 ppm (A) 60 13 (B) 40 0 (C) 5 0

Claims

1. A pyrazole compound of the formula:
wherein R1 is a C1-C8 alkyl group, a C2-C8 alkenyl group or a C3-C8 alkynyl group, these groups being unsubstituted or substituted with halogen, hydroxy and/or C1-C6 alkoxy, or a group of the formula:
wherein R5 is a hydrogen atom, a halogen atom, a hydroxy group,a cyano group, a nitro group, a C1-C4 alkyl group, a halo (C1-C4) alkyl group, a C1-C4 alkoxy group, a halo (C1-C9) alkoxy group, a C1-C4 alkylthio group, a halo (C1-C4) alkylthio group, a C2-C4 alkenyl group, a C2-C4 alkynyl group, a C2-C4 alkenyloxy group, a C2-C4 alkynyloxy group, a C2-C4 alkenylthio group, a C2-C4 alkynylthio group, a halo(C2-C4) alkenyl group, a halo(C2-C4) alkynyl group, a halo (C2-C4) alkenyloxy group, a halo (C2-C4) alkynyloxy group or a halo (C2-C4)alkenylthio group and n is an integer of 1 to 5;
R2 and R3 are the same or different and each represent a hydrogen atom, a halogen atom or a C1-C3 alkyl group;
R4 is a hydrogen atom, a halogen atom, a C1-C4 alkyl group or a halo (C1-C4) alkyl group;
A is either one of the formulae:
wherein R6, R7, R8 and R9 are the same or different and each represent a hydrogen atom, a halogen atom or a C1-C3 alkyl group, X is an oxygen atom, a sulfur atom, a methylene group, a carbonyl group, a sulfoxide group, a sulfonyl group or a single bond when R1 is the group of the formula: wherein R5 and n are each as defined above;
or a group of the formula: wherein R10 and R11 are the same or different and each represent a hydrogen atom, a halogen atom or a C1-C3 alkyl group, X is an oxygen atom, a sulfur atom, a methylene group, a carbonyl group, a sulfoxide group, a sulfonyl group or a single bond, Y is an oxygen atom, a sulfur atom or a methylene group and p is an integer of 1 to 4 when R1 is a C1-C8 alkyl group, a C2-C8 alkenyl group or a C3-C8 alkynyl group, these groups being unsubstituted or substituted with halogen, hydroxy and/or C1-C6 alkoxy;
~ is an integer of 0 to 2; and m is an integer of 1 to 3.

2. The compound according to claim 1, wherein R1 is a group of the formula: wherein R5 is a hydrogen atom, a halogen atom, a hydroxy group, a cyano group, a nitro group, a C1-C4 alkyl group, a halo (C1-C4)alkyl group, a C1-C4 alkoxy group, a halo (C1-C4) alkoxy group, a C1-C4 alkylthio group, a halo (C1-C4) alkylthio group, a C2-C4 alkenyl group, a C2-C4 alkynyl group, a C2-C4 alkenyloxy group, a C2-C4 alkynyloxy group, a C2-C4 alkenylthio group, a C2-C4 alkynylthio group, a halo (C2-C4) alkenyl group, a halo (C2-C4) alkynyl group, a halo (C2-C4) alkenyloxy group, a halo (C2-C4) alkynyloxy group or a halo (C2-C4) alkenylthio group and n is an integer of 1 to 5;
R2 and R3 are the same or different and each represent a hydrogen atom, a halogen atom or a C1-C3 alkyl group;
R4 is a hydrogen atom, a halogen atom, a C1-C4 alkyl group or a halo (C1-C4) alkyl group;
A is either one of the formulae:
wherein R6, R7, R8 and R9 are the same or different and each represent a hydrogen atom, a halogen atom or a C1-C3 alkyl group, X is an oxygen atom, a sulfur atom, a methylene group, a carbonyl group, a sulfoxide group, a sulfonyl group or a single bond;
~ is an integer of 0 to 2; and m is an integer of 1 to 3.

3. The compound according to claim 1, wherein R1 is a C1-C8 alkyl group, a C2-C8 alkenyl group or a C3-C8 alkynyl group, these groups being unsubstituted or substituted within, halogen, hydroxy, and/or C1-C6 alkoxy;
R2 and R3 are the same or different and each represent a hydrogen atom, a halogen atom or a C1-C3 alkyl group;
R4 is a hydrogen atom, a halogen atom, a C1-C4 alkyl group or a halo (C1-C4) alkyl group:
A is a group of the formula: wherein R10 and R11 are the same or different and each represent a hydrogen atom, a halogen atom or a C1-C3 alkyl group, X is an oxygen atom, a sulfur atom, a methylene group, a carbonyl group, a sulfoxide group, a sulfonyl group or a single bond, Y is an oxygen atom, a sulfur atom or a methylene group and p is an integer of 1 to 4;
~ is an integer of 0 to 2; and m is an integer of 1 to 3.

4. The compound according to claim 1, which has the formula:
wherein R1 is a phenyl group or a 3,5-difluorophenyl group.

5. The compound according to claim 1, which has the formula:
wherein R1 is a 2-methylpropyl group, a 2,2-dimethylpropyl group, a 2-methylbutyl group, a 2-methyl-2-propenyl group, a 3-methylbutyl group, an allyl group, a 2-chloroallyl group, a 3,3-dimethylbutyl group, a pentyl group, a 3-chloropropyl group or a propargyl group.

6. The compound according to claim 1, which has the formula:
wherein R1 is a 2,2-dimethylpropyl group, a 2-methylbutyl group or an isopropoxymethyl group.

7. The compound according to claim 1, which has the formula:

8. A pesticidal composition which comprises as the active ingredient the pyrazole compound according to claim 1 and an inert carrier or diluent.

9. A method for controlling pests which comprises applying a pesticidally effective amount of the pyrazole compound according to claim 1 to pests.

10. Use of the pyrazole compound according to claim 1 as a pesticide.