3-(substituted pyridyl)-1,2,4-triazole compounds

Details 3-(substituted pyridyl)-1,2,4-triazole compounds 3-(substituted pyridyl)-1,2,4-triazole compounds

1999-10-22

2002-07-02

Morris, Patricia L. (Department: 1625)

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Having -c-, wherein x is chalcogen, bonded directly to...

C546S272400

Reexamination Certificate

active

06413992

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 substituted pyridyl triazole derivatives especially useful for the control of insects and mites.
More specifically, the invention provides novel insecticidally active compounds of the formula (1)
wherein
Z is pyridyl, optionally substituted with up to four groups independently selected from the group consisting of Cl, F, methyl, halomethyl, methoxy, halomethoxy, and methylthio;
one of X and Y is H, lower alkyl, haloalkyl, lower alkenyl, lower alkynyl, alkoxyalkyl, phenyl, or substituted phenyl;
the other of X and Y is a group selected from
 wherein
R
2
is halo, lower alkyl, haloalkyl, lower alkenyl, lower alkynyl, or alkoxyalkyl;
R
3
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, pyridyloxy, substituted pyridyl, substituted pyridyloxy, phenoxy, substituted phenoxy, 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
, —NCH
3
NH
2
,
R
4
and R
5
are independently H, halo, lower alkyl, lower alkoxy, haloalkyl, haloalkoxy, CN, NO
2
, CO
2
R
6
, CON(R
6
)
2
, or S(O)
m
alkyl, or
R
4
and R
5
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
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 or N-oxide thereof.
The priority document described compounds of the formula
wherein
Z is 2-pyridyl, 3-pyridyl, or 4-pyridyl, optionally substituted with up to four groups independently selected from the group consisting of Cl, F, methyl, halomethyl, methoxy, and halomethoxy;
X is lower alkyl, haloalkyl, lower alkenyl, lower alkynyl, or alkoxyalkyl;
Y is a group selected from
 wherein
R is lower alkyl, haloalkyl, lower alkenyl, lower alkynyl, or alkoxyalkyl;
R 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
4
and R
5
are independently H, halo, lower alkyl, lower alkoxy, haloalkyl, haloalkoxy, CN, CO
2
R
6
, CON(R
6
)
2
, or S(O)
m
alkyl, or
R
4
and R
5
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
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 or N-oxide thereof.
Preferred compounds of formula (1) include the following classes:
(1) Compounds of formula (1) wherein wherein one of X and Y is lower alkyl, haloalkyl, lower alkenyl, lower alkynyl, substituted phenyl, or alkoxyalkyl; and the other of X and Y is optionally substituted phenyl, pyridyl, thienyl, cyclopropyl, or thiazolyl;
(2) Compounds of formula (1) wherein Z is a 4-pyridyl group optionally substituted with up to four groups independently selected from Cl, F, methyl, halomethyl, methylthio, methoxy, and halomethoxy.
(3) Compounds of class (2) wherein Z is a 4-pyridyl group of the formula
 wherein R
7
and R
8
are independently H, Cl, F, methyl, halomethyl, methoxy, or halomethoxy.
(4) Compounds of class (3) wherein R
7
and R
8
are independently methyl, F or Cl.
(5) Compounds of class (4) wherein R
7
and R
8
are both F, where R
7
is chloro and R
8
is methyl, or where R
7
is fluoro and R
8
is methyl.
(6) Compounds of class (4) wherein R
7
and R
8
are both Cl.
(7) Compounds of formula (1), and particularly compounds of class (1), (2), (3), (4), (5), or (6) as defined above, wherein Y is a group of the formula
 where R
2
, R
3
, R
4
, and R
5
are as defined in formula (1)
(8) Compounds of formula (1), and particularly compounds of class (1), (2), (3), (4), (5), or (6) as defined above, wherein Y is a group of the formula
 where R
3
, R
4
, and R
5
are as defined in formula (1).
(9) Compounds of class (7) wherein Y is a group of the formula
 where R
3
is an electron withdrawing group such as Cl, Br, CF
3
or NO
2
.
(10) Compounds of formula (1), and particularly compounds of class (1), (2), (3), (4), (5), or (6) as defined above, wherein Y is a group of the formula
 where R
3
, R
4
, and R
5
are as defined in formula (1).
(11) Compounds of formula (1), and particularly compounds of class (1), (2), (3), (4), (5), or (6) as defined above, wherein Y is a group of the formula
 where R
3
, R
4
, and R
5
are as defined in formula (1).
(12) Compounds of class (11) wherein R
3
, R
4
, and R
5
are independently selected from H, halo, alkyl, and alkoxy.
(13) Compounds of class (12) wherein R
3
, R
4
, and R
5
are independently selected from H, alkyl, and halo.
(14) Compounds of class (13) wherein R
3
, R
4
, and R
5
are independently selected from H, methyl, Cl, and Br.
(15) Compounds of formula (1), and particularly compounds of class (1), (2), (3), (4), (5), or (6) as defined above, wherein Y is a group of the formula
 where R
3
, R
4
, and R
5
are as defined in formula (1).
(16) Compounds of formula (1) or any one of classes (1) through (15) wherein X is methyl.
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 hydr

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