Process and intermediates for preparing 3-(substituted...

Details Process and intermediates for preparing 3-(substituted... Process and intermediates for preparing 3-(substituted...

1999-09-03

2001-07-17

Morris, Patricia L. (Department: 1612)

Organic compounds -- part of the class 532-570 series

Organic compounds

Amino nitrogen containing

Reexamination Certificate

active

06262305

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 thienyl and furanyl 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
Ar is substituted phenyl;
Y is O or S;
R
2
is lower alkyl, haloalkyl, lower alkenyl, lower alkynyl, or alkoxyalkyl;
R
3
is selected from H, halo, lower alkyl, (C
7
-C
21
) straight or branched chain alkyl, hydroxy, lower alkoxy, haloalkyl, haloalkoxy, alkoxyalkyl, alkoxyalkoxy, lower alkenyl, lower alkynyl, haloalkenyl, CN, NO
2
, COR
6
, CO
2
R
6
, CON(R
6
)
2
, (C
3
-C
6
) cycloalkyl, S(O)
m
R
6
, —OSO
2
R
6
, SCN, —(CH
2
)
n
R
6
, —CH═CHR
6
, —C—CR
6
, —(CH
2
)
q
OR
6
, (CH
2
)
q
SR
6
, —(CH
2
)
q
NR
6
R
6
O(CH
2
)
q
R
6
, —S (CH
2
)
q
R
6
, —NR
6
(CH
2
)
q
R
6
,
—Si(R
7
)
3
pyridyl, substituted pyridyl, isoxazolyl, substituted isoxazolyl, naphthyl, substituted naphthyl, phenyl, substituted phenyl, thienyl, substituted thienyl, pyrimidyl, substituted pyrimidyl, pyrazolyl, or substituted pyrazolyl;
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
if R
4
and R
5
are attached to adjacent carbon atoms, they may join 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
6
is H, lower alkyl, haloalkyl, lower alkenyl, lower alkynyl, phenyl, or substituted phenyl;
R
7
is lower alkyl;
m is 0, 1, or 2;
n is 1 or 2;
p is an integer from 2 to 6; and
q is 0 or 1;
or a phytologically acceptable acid addition salt thereof.
A preferred group of compounds are those of formula (1A)
wherein
R
1
and R
1
′ are independently H, Cl, F, methyl, halomethyl, methoxy, or halomethoxy;
Y is O or S;
R
2
is 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, substituted pyridyl, isoxazolyl, substituted isoxazolyl, naphthyl, substituted naphthyl, phenyl, substituted phenyl, —(CH
2
) R
6
, —CH=CHR
6
, —C═CR
6
, —CH
2
OR
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 thereof.
Preferred compounds of formula (1A) include the following classes:
a) compounds of formula (1A) wherein R
1
′ is F;
b) compounds of formula (1A) wherein Y is sulfur;
c) compounds of formula (1A), and pa rticularly compounds of the foregoing classes a) and b), wherein R
1
and R
1
′ are independently Cl or F;
d) compounds of formula (1A), and particularly compounds of the foregoing classes a) through c) wherein R
1
and R
1
′ are both F;
e) compounds of formula (1A), and particularly compounds of the foregoing classes a) through c) wherein R
1
and R
1
′ are both Cl;
f) compounds of formula (1A), and particularly compounds of the foregoing classes a) through c) wherein R
1
is Cl and R
1
′ is F;
g) compounds of formula (1A), and particularly compounds of one of the foregoing classes a) through f) wherein R
2
is methyl;
h) compounds of formula (1A), and particularly compounds of one of the foregoing classes a) through g) wherein R
3
, R
4
, and R
5
are independently selected from H, halo, methyl, and methoxy;
i) compounds of formula (1A), and particularly compounds of one of the foregoing classes a) through g) wherein R
3
, R
4
, and R
5
are independently H or halo;
j) compounds of formula (1A), and particularly compounds of one of the foregoing classes a) through g) wherein R
3
, R
4
, and R
5
are independently H, Cl, or Br;
k) compounds of formula (1A), an particularly compounds of one of the foregoing classes a) through g) wherein R
3
, R
4
, and R
5
are each halo;
l) compounds of formula (1A), and particularly compounds of one of the foregoing classes a) through g) wherein R
3
, R
4
, and R
5
are each chloro.
A particularly preferred class of compounds includes those of formula (1B)
wherein
R
1
and R
1
′ are independently F or Cl;
R
2
is lower alkyl, with methyl being most preferred; and
R
3
, R
4
and R
5
are independently H, Cl, or Br.
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” and “haloalkyl” refer to methoxy and lower alkyl groups substituted with one or more halo atoms.
The terms “halomethoxy” and “haloalkoxy” refer to methyl 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 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,

Affiliated with

Also associated with

Rating

Process and intermediates for preparing 3-(substituted... does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Process and intermediates for preparing 3-(substituted..., we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Process and intermediates for preparing 3-(substituted... will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-2522966