Compounds having fungicidal activity and processes to make...

Details Compounds having fungicidal activity and processes to make... Compounds having fungicidal activity and processes to make...

2003-06-09

2004-11-09

Kumar, Shailendra (Department: 1621)

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

Organic compounds

Carboxylic acid esters

C514S478000, C514S479000, C514S596000, C514S597000, C514S598000, C514S546000, C514S469000, C514S522000, C564S048000, C564S049000, C546S291000, C546S292000, C549S467000, C558S413000

Reexamination Certificate

active

06815556

ABSTRACT:

FIELD OF THE INVENTION
This invention is related to the field of compounds having fungicidal activity and processes to make and use such compounds.
BACKGROUND OF THE INVENTION
Our history is riddled with outbreaks of fungal diseases that have caused widespread human suffering. One need look no further than the Irish potato famine, which occurred from 1845 to 1860, where an estimated 1,000,000 people died, and an estimated 1,500,000 people emigrated, to see the effects of a fungal disease. Fungicides are compounds, of natural or synthetic origin, which act to protect plants against damage caused by fungi. Current methods of agriculture rely heavily on the use of fungicides. In fact, some crops cannot be grown usefully without the use of fungicides. Using fungicides allows a grower to increase the yield and the quality of the crop and consequently, increase the value of the crop. In most situations, the increase in value of the crop is worth at least three times the cost of the use of the fungicide. However, no one fungicide is useful in all situations. Consequently, research is being conducted to produce fungicides that are safer, that have better performance, that are easier to use, and that cost less. In light of the above, the inventors provide this invention.
SUMMARY OF THE INVENTION
It is an object of this invention to provide compounds that have fungicidal activity. It is an object of this invention to provide processes that produce compounds that have fungicidal activity. It is an object of this invention to provide processes that use compounds that have fungicidal activity. In accordance with this invention, processes to make and processes to use compounds having a general formula according to formula one, and said compounds are provided. While all the compounds of this invention have fungicidal activity, certain classes of compounds may be preferred for reasons such as, for example, greater efficacy or ease of synthesis.
Throughout this document, all temperatures are given in degrees Celsius and all percentages are weight percentages, except for percent yields which are mole percentages, unless otherwise stated. The term “alkyl”, “alkenyl”, or “alkynyl” refers to an unbranched, or branched, chain carbon group. The term “alkoxy” refers to an unbranched, or branched, chain alkoxy group. The term “haloalkyl” refers to an unbranched, or branched, alkyl group substituted with one or more halo atoms, defined as F, Cl, Br, and I. The term “haloalkoxy” refers to an unbranched, or branched, chain alkoxy group substituted with one or more halo atoms. The term “alkoxylalkyl” refers to an unbranched, or branched, chain alkyl group substituted with one or more alkoxy groups. The term “alkoxyalkoxy” refers to an unbranched, or branched, chain alkoxy group substituted with one or more alkoxy groups. The term “aryl” refers to a phenyl or naphthyl group. The term “Me” refers to a methyl group. The term “Et” refers to an ethyl group. The term “Pr” refers to a propyl group. The term “Bu” refers to a butyl group. The term “EtOAc” refers to ethyl acetate. The term “ppm” refers to parts per million. The term, “psi” refers to pounds per square inch.
Heteroaryl is defined by the following Formula Two
wherein 2A represents a 5- or 6-membered ring and 2B represents a 9- or 10-membered fused bicyclic ring in which each of X
1
-X
5
is independently a bond, O, S, NR
7
, N, or CR, where R is selected from the group consisting of halo, C
1-4
alkyl, C
2-4
alkenyl, C
2-4
alkynyl, C
1-4
alkoxy, C
1-4
haloalkyl, C
1-4
haloalkoxy, C
1-4
alkoxyalkyl, C
1-4
alkoxyalkoxy, CN, NO
2
, OH, SCN, C(═O)R
6
, C(═NR
6
)R
6
, S(O
n
)R
6
where n=0, 1 or 2, aryl, aryloxy, heteroaryl, and heteroaryloxy, and where no more than one of X
1
-X
5
is O, S, or NR
7
, no more than one of X
1
-X
5
is a bond, when any one of X
1
-X
5
is S, O or NR
7
, one of the adjacent X
1
-X
5
must represent a bond; and at least one of X
1
-X
5
must be O, S, NR
7
or N.
Examples of such heteroaryls are pyridinyl, pyridazinyl, pyrimidinyl, pyrazinyl, pyrrolyl, pyrazolyl, imidazolyl, quinolinyl, isoquinolinyl, phthalazinyl, quinazolinyl, quinoxalinyl, cinnolinyl, indolyl, isoindolyl, indazolyl, thienyl, benzothienyl, furanyl, benzofuranyl, thiazolyl, benzothiazolyl, isothiazolyl, benzoisothiazolyls, oxazolyl, benzoxazolyl, isoxazolyl, and benzoisoxazolyl.


REFERENCES:
patent: 5346907 (1994-09-01), Kerwin et al.

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