Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Reexamination Certificate
1999-10-22
2002-07-02
Morris, Patricia L. (Department: 1612)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
C514S369000, C514S370000, C514S371000, C548S182000, C548S183000, C548S184000, C548S185000, C548S186000, C548S189000, C548S190000, C548S195000, C548S198000, C548S200000, C548S201000, C548S202000, C548S266200
Reexamination Certificate
active
06413997
ABSTRACT:
FIELD OF THE INVENTION
This invention provides new compounds that are useful as insecticides and acaricides, new synthetic procedures and intermediates for preparing the compounds, pesticide compositions containing the compounds, and methods of controlling insects and mites using the compounds.
BACKGROUND OF THE INVENTION
There is an acute need for new insecticides and acaricides. Insects and mites are developing resistance to the insecticides and acaricides in current use. At least 400 species of arthropods are resistant to one or more insecticides. The development of resistance to some of the older insecticides, such as DDT, the carbamates, and the organophosphates, is well known. But resistance has even developed to some of the newer pyrethroid insecticides and acaricides. Therefore a need exists for new insecticides and acaricides, and particularly for compounds that have new or atypical modes of action.
A number of 3,5-diphenyl-1H-1,2,4-triazole derivatives have been described in the literature as having acaricidal activity. U.S. Pat. No. 5,482,951; JP 8092224, EP572142, JP 08283261. To applicants knowledge, however, none of these compounds has become a commercial product. Nitro furanyl triazoles are described by L. E. Benjamin and H. R. Snyder as antimicrobials (
J. Heterocyclic Chem.
1976, 13, 1115) and by others as antibacterials (
J. Med. Chem.
1973, 16(4), 312-319;
J. Med. Chem.
1974, 17(7), 756-758). The present invention provides novel compounds with commercial level activity against mites and insects.
SUMMARY OF THE INVENTION
This invention provides novel compounds especially useful for the control of insects and mites.
More specifically, the invention provides novel insecticidally active compounds of the formula (1)
wherein
Ar is substituted phenyl;
R
1
is lower alkyl, haloalkyl, lower alkenyl, lower alkynyl, or alkoxyalkyl;
HET is a group selected from
R
2
is selected from H, halo, lower alkyl, (C
7
-C
21
) straight chain alkyl, hydroxy, lower alkoxy, haloalkyl, haloalkoxy, alkoxyalkyl, alkoxyalkoxy, lower alkenyl, haloalkenyl, CN, NO
2
, CO
2
R
6
, CON(R
6
)
2
, (C
3
-C
6
) cycloalkyl, S(O)
m
R
6
, SCN, pyridyl, substituted pyridyl, isoxazolyl, substituted isoxazolyl, naphthyl, substituted naphthyl, phenyl, substituted phenyl, —(CH
2
)
n
R
6
, —CH═CHR
6
, —C≡CR
6
, —CH
2
OR
6
, —CH
2
SR
6
, —CH
2
NR
6
R
6
, —OCH
2
R
6
, —SCH
2
R
6
, —NR
6
CH
2
R
6
,
R
3
is H, halo, lower alkyl, lower alkoxy, haloalkyl, haloalkoxy, CN, CO
2
R
6
, CON(R
6
)
2
, or S(O)
m
alkyl, or
R
2
and R
3
combine to form a 5 or 6 member saturated or unsaturated carbocyclic ring which may be substituted by 1 or 2 halo, lower alkyl, lower alkoxy or haloalkyl groups;
R
4
is H, lower alkyl, haloalkyl, lower alkenyl, lower alkynyl, phenyl, or substituted phenyl;
R
6
is H, lower alkyl, haloalkyl, lower alkenyl, lower alkynyl, phenyl, or substituted phenyl;
m is 0, 1, or 2; and
n is 1 or 2;
p is an integer from 2 to 6;
or a phytologically acceptable acid addition salt thereof.
Preferred compounds of formula (1) include the following classes:
(1) Compounds of formula (1) wherein Ar is a group of the formula
wherein R
7
and R
8
are independently H, Cl, F, methyl, halomethyl, methoxy, or halomethoxy.
(2) Compounds of class (1) wherein R
7
and R
8
are independently F or Cl.
(3) Compounds of class (3) wherein R
7
and R
8
are both F.
(4) Compounds of class (3) wherein R
7
and R
8
are both Cl.
(5) Compounds of class (3) wherein R
7
is F and R
8
is Cl.
(6) Compounds of formula (1), and particularly compounds of any one of classes (1) through (5) defined above, wherein
R
1
is methyl.
(7) Compounds of any one of classes (1) through (6) wherein HET is
and R
2
and R
3
are as defined in formula (1).
(8) Compounds of any one of classes (1) through (6) wherein HET is
and R
2
and R
3
are as defined in formula (1).
(9) Compounds of any one of classes (1) through (6) wherein HET is
and R
2
and R
3
are as defined in formula (1).
(10) Compounds of any one of classes (1) through (6) wherein HET is
and R
2
and R
3
are as defined in formula (1).
(11) Compounds of any one of classes (1) through (6) wherein HET is
and R
2
and R
3
are as defined in formula (1).
(12) Compounds of any one of classes (1) through (6) wherein HET is
and R
2
and R
3
are as defined in formula (1).
(13) Compounds of any one of classes (1) through (6) wherein HET is
and R
2
and R
3
are as defined in formula (1).
(14) Compounds of any one of classes (1) through (6) wherein HET is
and R
2
and R
3
are as defined in formula (1).
(15) Compounds of any one of classes (1) through (6) wherein HET is
and R
2
and R
3
are as defined in formula (1).
(16) Compounds of any one of classes (1) through (6) wherein HET is
and R
2
is as defined in formula (1).
(17) Compounds of any one of classes (1) through (6) wherein HET is
and R
2
is as defined in formula (1).
(18) Compounds of any one of classes (1) through (6) wherein HET is
and R
2
, R
3
, and R
4
are as defined in formula (1).
(19) Compounds of any one of classes (1) through (6) wherein HET is
and R
2
, R
3
, and R
4
are as defined in formula (1).
(20) Compounds of any one of classes (1) through (6) wherein HET is
and R
2
, R
3
, and R
4
are as defined in formula (1).
(21) Compounds of any one of classes (1) through (6) wherein HET is
and R
2
, R
3
, and R
4
are as defined in formula (1).
(22) Compounds of any one of classes (1) through (6) wherein HET is
and R
2
, R
3
, and R
4
are as defined in formula (1).
(23) Compounds of any one of classes (1) through (6) herein HET is
and R
2
, R
3
, and R
4
are as defined in formula (1).
(24) Compounds of any one of classes (1) through (6) wherein HET is
and R
2
, R
3
, and R
4
are as defined in formula (1).
The invention also provides new processes and intermediates for preparing compounds of formula (1) as well as new compositions and methods of use, which will be described in detail hereinafter.
DETAILED DESCRIPTION OF THE INVENTION
Throughout this document, all temperatures are given in degrees Celsius, and all percentages are weight percentages unless otherwise stated.
The term “lower alkyl” refers to (C
1
-C
6
) straight hydrocarbon chains and (C
3
-C
6
) branched and cyclic hydrocarbon groups.
The terms “lower alkenyl” and “lower alkynyl” refer to (C
2
-C
6
) straight hydrocarbon chains and (C
3
-C
6
) branched hydrocarbon groups containing at least one double or triple bond, respectively.
The term “lower alkoxy” refers to —O-lower alkyl.
The terms “halomethyl”, “haloalkyl”, and “haloalkenyl” refer to methyl, lower alkyl, and lower alkenyl groups substituted with one or more halo atoms.
The terms “halomethoxy” and “haloalkoxy” refer to methoxy and lower alkoxy groups substituted with one or more halo atoms.
The term “alkoxyalkyl” refers to a lower alkyl group substituted with a lower alkoxy group.
The term “alkoxyalkoxy” refers to a lower alkoxy group substituted with a lower alkoxy group.
The terms “substituted naphthyl”, “substituted thienyl,” “substituted pyrimidyl,” “substituted pyrazolyl,” “substituted pyridyl,” and “substituted isoxaxolyl” refer to the ring system substituted with one or more groups independently selected from halo, halo (C
1
-C
4
) alkyl, CN, NO
2
, (C
1
-C
4
) alkyl, (C
3
-C
4
) branched alkyl, phenyl, (C
1
-C
4
) alkoxy, or halo (C
1
-C
4
) alkoxy.
The term “substituted phenyl” refers to a phenyl group substituted with one or more groups independently selected from halo, (C
1
-C
10
) alkyl, branched (C
3
-C
6
) alkyl, halo (C
1
-C
7
) alkyl, hydroxy (C
1
-C
7
) alkyl, (C
1
-C
7
) alkoxy, halo (C
1
-C
7
) alkoxy, phenoxy, phenyl, NO
2
, OH, CN, (C
1
-C
4
) alkanoyl, benzoyl, (C
1
-C
4
) alkanoyloxy, (C
1
-C
4
) alkoxycarbonyl, phenoxycarbonyl, or benzoyloxy.
Unless otherwise indicated, when it is stated that a group may be substituted with one or more substituents selected from an identified class, it is intended that the substituents may be independently selected from the class.
Synthesis
Compounds of formula (1) can be prepared by the methods described i
Ash Mary L.
Denny Carl P.
DeVries Donald H.
Johnson Peter L.
Pechacek James T.
Dow AgroSciences LLC
Mixan Craig E.
Morris Patricia L.
Stuart Donald R.
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