Dihalopropene compounds, insecticidal/acaricidal agents...

Details Dihalopropene compounds, insecticidal/acaricidal agents... Dihalopropene compounds, insecticidal/acaricidal agents...

2000-03-07

2001-07-31

Seaman, D. Margaret (Department: 1625)

Plant protecting and regulating compositions

Plant growth regulating compositions

Organic active compound containing

C504S269000, C504S270000, C504S271000, C504S275000, C504S280000, C504S283000, C548S161000, C548S165000, C548S182000, C548S190000, C548S200000, C548S202000, C548S203000, C548S221000, C548S222000, C548S225000, C548S233000, C548S235000, C548S304400, C548S306400, C548S307400, C548S316400, C548S326500, C548S335100

Reexamination Certificate

active

06268313

ABSTRACT:

TECHNICAL FIELD
The present invention relates to dihalopropene compounds, insecticidal/acaricidal agents containing these compounds as active ingredients, and intermediates for their production.
1. Background Art
As disclosed in JP-A 48-86835/1973 and JP-A 49-1526/1974, for example, it is well known that some kinds of propene compounds can be used as an active ingredient of insecticides.
In view of their insecticidal/acaricidal activity, it cannot always be said that these compounds are satisfactorily effective for the control of noxious insects, mites and ticks.
2. Disclosure of Invention
The present inventors have intensively studied to find a compound having excellent insecticidal/acaricidal activity. As a result, they have found that particular dihalopropene compounds have satisfactory insecticidal/acaricidal activity for the control of noxious insects, mites and ticks, thereby completing the present invention.
That is, the present invention provides a dihalopropene compound (hereinafter referred to as the present compound) of the general formula:
wherein Z is oxygen, sulfur or NR
4
(wherein R
4
is hydrogen or C
1
-C
3
alkyl); Y is oxygen, sulfur or NH; X's are independently chlorine or bromine; R
2
, R
3
and R
10
are; independently halogen, C
1
-C
3
haloalkyl or C
1
-C
3
alkyl; t is an integer of 0 to 2; and R
1
is Q
1
, Q
2
, Q
3
, Q
4
, Q
5
, Q
6
or Q
7
of the general formula:
wherein A is an optionally substituted heterocyclic ring group, provided that when A is an optionally substituted heterocyclic ring group containing two oxygen atoms and a condensed benzene ring, A is optionally substituted 1,3-benzodioxolan-2-yl or optionally substituted 1,4-benzodioxan-2-yl; B is oxygen, S(O)
q
, NR
9
, C(═G
1
)G
2
or G
1
C(═G
2
); q is an integer of 0 to 2; R
9
is hydrogen, acetyl or C
1
-C
3
alkyl; G
1
and G
2
are independently oxygen or sulfur; R
5
, R
6
, R
7
, R
11
and R
12
are independently hydrogen, C
1
-C
3
akyl or trifluoromethyl; R
13
and R
14
are independently hydrogen, C
1
-C
3
alkyl, trifluoromethyl or halogen; p is an integer of 0 to 6; and s is an integer of 1 to 6.
The present invention further provides an insecticidal/acaricidal agent containing the above dihalopropene compound as an active ingredient.
The present invention further provides the following compounds which are useful as intermediates for producing some of the present compounds:
a phenol compound which is 3,5-dichloro-4-(2-(2-(4-chlorophenyl)-1,3-dioxolan-4-yl)ethoxy)phenol;
compounds of the general formula:
 wherein R
5
, R
6
and R
7
are independently hydrogen, C
1
-C
3
alkyl or trifluoromethyl; R
15
is halogen, C
1
-C
3
alkyl, C
1
-C
3
haloalkyl, C
1
-C
3
alkoxy or C
1
-C
3
haloalkoxy; R
2
, R
3
and R
10
are independently halogen, C
1
-C
3
alkyl or C
1
-C
3
haloalkyl; t is an integer of 0 to 2; u is an integer of 1 to 4; w is an integer of 1 to 4; and B
1
is oxygen, S(O)
q
or NR
9
wherein R
9
is hydrogen, acetyl or C
1
-C
3
alkyl and q is an integer of 0 to 2;
compounds of the general formula [I] wherein R
5
, R
6
and R
7
are all hydrogen; and R
2
and R
3
are independently halogen or C
1
-C
3
alkyl; and
2-(3-methanesulfonyloxypropyloxy)-5-trifluoromethylpyridine.
DETAILED DESCRIPTION OF THE INVENTION
The variables in the above formulae for the present compounds and their intermediates can take the following specific examples.
Examples of the C
1
-C
3
alkyl group represented by R
2
, R
3
, R
4
, R
5
, R
6
, R
7
, R
9
, R
10
, R
11
, R
12
, R
13
or R
14
are methyl, ethyl, n-propyl and isopropyl.
Examples of the halogen atom represented by R
13
or R
14
are fluorine, chlorine, bromine and iodine.
Examples of the heterocyclic ring in the optionally substituted heterocyclic ring group represented by A are isoxazole, isothiazole, thiazole, 1,3,4-thiadiazole, pyrrole, furan, thiophene, pyrazole, imidazole, 1,2,3-triazole, 1,2,4-triazole, 1,2,3,4-tetrazole, pyridine, pyridaiine, pyrimidine, pyrazine, 1,2,4-triazine, 1,3,5-triazinie, indole, benzofuran, thianaphthalene, indazole, benzimidazole, benzotriazole, benzisoxazole, benzoxazole, benzothiazole, quinoline, isoquinoline, quinoxaline, quinazole, piperidine, piperazine, tetrahydrofuran, tetrahydropyran, pyrazoline, phthalimide, dioxane, dioxolane and benzodioxolane.
Examples of the substituent on the optionally substituted heterocyclic ring group represented by A are those of the general formula: (R
8
)
r
(wherein R
8
is halogen, nitro, cyano, C
1
-C
4
alkyl, C
1
-C
3
haloalkyl, C
1
-C
4
alkoxy, C
1
-C
3
haloalkoxy, C
1
-C
3
alkylthio, C
1
-C
3
haloalkylthio, C
1
-C
2
alkylsulfinyl, C
1
-C
2
alkylsulfonyl, C
1
-C
2
haloalkylsulfinyl, C
1
-C
2
haloalkylsulfonyl, C
2
-C
4
alkenyl, C
2
-C
4
haloalkenyl, C
2
-C
4
alkynyl, C
2
-C
4
haloalkynyl, amino, dimethylamino, acetamido, acetyl, haloacetyl, formyl, carboxyl, methoxycarbonyl, C
3
-C
6
cycloalkyl, (C
1
-C
2
alkyl)aminocarbonyl or [di(C
1
-C
2
alkyl)amino]carbonyl, or R
8
is phenyl, benzyl, phenoxy, benzyloxy or pyridyloxy, each of which is optionally substituted with halogen, C
1
-C
4
alkyl, C
1
-C
3
haloalkyl, C
1
-C
4
alkoxy or C
1
-C
3
haloalkoxy; and r is an integer of 0 to 7.
Examples of the halogen atom represented by R
8
or present in R
8
are fluorine, chlorine, bromine and iodine.
Examples of the C
1
-C
4
alkyl group represented by R
8
or present in R
8
are methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl and tert-butyl.
Examples of the C
1
-C
3
haloalkyl group represented by R
8
or present in R
8
are trifluoromethyl, difluoromethyl, bromodifluoromethyl, 2,2,2-trifluoroethyl, 2-fluoroethyl, 2-chloroethyl, 2-bromoethyl, 1-fluoroethyl, 1-chloroethyl, 1-bromoethyl, 2,2,3,3,3-pentafluoropropyl, 3,3,3-trifluoropropyl, 1-fluoropropyl, 2-chloropropyl and 3-bromopropyl.
Examples of the C
1
-C
4
alkoxy group represented by R
8
or present in R
8
are methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, sec-butoxy, isobutoxy and tert-butoxy.
Examples of the C
1
-C
3
haloalkoxy group represented by R
8
or present in R
8
are trifluoromethoxy, difluoromethoxy, bromofluoromethoxy, 2-fluoroethoxy, 2,2,2-trifluoroethoxy, 2-chloroethoxy, 2-bromoethoxy, 2-chloro-1,1,2-trifluoroethoxy, 2-bromo-1,1,2-trifluoroethoxy, 1,1,2,2-tetrafluoroethoxy, 1,2,2,3,3,3-hexafluoropropoxy, 3-fluoropropoxy, 3-chloropropoxy, 3-bromopropoxy, 2,2,3,3,3-pentafluoropropoxy, 3,3,3-trifluoropropoxy and 1,1,2,2,2-pentafluoroethoxy.
Examples of the C
1
-C
3
alkylthio group represented by R
8
are methylthio, ethylthio, n-propylthio and isopropylthio.
Examples of the C
1
-C
3
haloalkylthio group represented by R
8
are trifluoromethylthio, difluoromethylthio, bromodifluoromethylthio, 2,2,2-trifluoroethylthio, 2-chloro-1,1,2-trifluoroethylthio, 2-bromo-1,1,2-trifluoroethylthio, 1,1,2,2-tetrafluoroethylthio, 2-chloroethylthio, 2-fluoroethylthio, 2-bromoethylthio, 3-fluoropropylthio, 3-chloropropylthio, (3-bromopropyl)thio, 2,2,3,3,3-pentafluoropropylthio and 3,3,3-trifluoropropylthio.
Examples of the C
1
-C
2
alkylsulfinyl group represented by R
8
are methylsulfinyl and ethylsulfinyl.
Examples of the C
1
-C
2
alkylsulfonyl group represented by R
8
are methylsulfonyl and ethylsulfonyl.
Examples of the C
1
-C
2
haloalkylsulfinyl group represented by R
8
are trifluoromethylsulfinyl, 2,2,2-trifluoroethylsulfinyl and perfluoroethylsulfinyl.
Examples of the C
1
-C
2
haloalkylsulfonyl group represented by R
8
are trifluoromethylsulfonyl, 2,2,2-trifluoroethylsulfonyl and perfluoroethylsulfonyl.
Examples of the C
2
-C
4
alkenyl group represented by R
8
are vinyl, isopropenyl, 1-propenyl, 2-ethyl-1-propenyl, 1-methyl-1-propenyl, allyl, 2-methylpropenyl and 2-butenyl.
Examples of the C
2
-C
4
haloalkenyl group represented by R
8
are 2,2-dichloroethenyl, 2,2-dibromoethenyl, 3,3-dichloroallyl, 3,3-dibromoallyl, 2,3-dichloroallyl, 2,3-dibromoallyl, 2-chloro-2-propenyl, 3-chloro-2-propenyl, 2-bromo-2-propenyl and 3-chloro-2-butenyl.
Examples of the C
2
-C
4
alkynyl group represented by R
8
are ethynyl, 1-p

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