Substituted oxadiazines useful as pesticides

Details Substituted oxadiazines useful as pesticides Substituted oxadiazines useful as pesticides

2002-01-16

2003-02-04

Clardy, S. Mark (Department: 1616)

Plant protecting and regulating compositions

Plant growth regulating compositions

Organic active compound containing

C514S229200

Reexamination Certificate

active

06514911

ABSTRACT:

BACKGROUND OF THE INVENTION
1. Field of the Invention
The present invention is directed to a class of substituted oxadiazines that are useful as herbicides and, in some cases, as insecticides as well. Hereinafter, the tern “pesticide” will be employed as being generic to herbicides, insecticides, nematocides, and miticides. 2. Description of Related Art
Undesirable, uncultivated plants—often characterized simply as “weeds”—are able to reduce yields of cultivated plants and other useful agricultural crops by competing with to cultivated plants. As a result, weeds interfere with the growth of seeds, vegetables, fruits, and foliage. Weeds are able to cause this sort of undesirable result because of the tendency of weeds to compete aggressively with cultivated plants for available light and space, moisture, and nutrients in the soil. Furthermore, and as is well-known to those skilled in the crop-protection art, various commercially important food plants as well as plants that are used for structural and ornamental purposes are yet additionally vulnerable to the devastation caused by insect pests.
Weed control is essential for maximum production of many agronomic and horticultural crops including corn (
Zea mays
L.), cotton (Gossypium SP), sunflower (
Helianthus annus
L.), and soybeans (
Glycine max
(L.) Merr.). Weeds on noncropped areas may cause a fire hazard, undesirable drifting of sand or snow, and/or irritation to persons with allergies. Thus, suppression of undesirable weed growth is very advantageous.
Kryukov et al. (Zh. Vses. Khim. O-Va 1979 24(4) 393-5), Chem. Abs. 91, 193269e) describe the preparation of 2-heptafluoropropyl-6-phenyl-4,4-bis(trifluoromethyl)-4H-1,3,5-oxadiazine, but no biological activity or use was disclosed.
The following compounds that are useful in the practice of the present invention are known to be commercially available, but no biological activity is known to have been disclosed: 2-(3-chlorophenyl)-4,4,6-tris(trifluoromethyl)-4H-1,3,5-oxadiazine; 2-(2-chlorophenyl)-6-(pentafluoroethyl)-4,4-bis(trifluoromethyl)-4H-1,3,5-oxadiazine; 2-(pentafluoroethyl)-6-{4-(trifluoromethoxy)phenyl}-4,4-bis(trifluoromethyl)-4H-1,3,5-oxadiazine; and 2-(3,5-dichlorophenyl)-6-(pentafluoroethyl)-4,4-bis(trifluoromethyl)-4H-1,3,5-oxadiazine.
SUMMARY OF THE INVENTION
It has now been found that a particular class of substituted oxadiazines unexpectedly provides excellent pre-emergence and postemergence herbicidal properties and, in some cases, also provides insecticidal properties.
The present invention relates to and has as an object the use of particular 1,3,5-oxadiazines for combating undesirable plant growth, including noxious weeds in agricultural crops. Further objects will become apparent from a study of the present specification and accompanying examples.
More particularly, the present invention is directed to a method of controlling pests comprising contacting said pests with an effective amount of a pesticide comprising a composition comprising:
(A) a compound of the formula:
wherein R
1
is a straight-chain perfluoroalkyl group or a partially fluorinated straight-chain alkyl group and R is a phenyl group or a substituted phenyl group having at least one substituent, wherein the substituent is selected from the group consisting of amino, formyl, halo, alkyl, alkoxy, haloalkyl, haloalkoxy, and nitro, and
(B) a suitable carrier therefor.
In a preferred embodiment, the present invention is directed to a method of controlling unwanted plant life in a location where such control is desirable by application of a herbicidally effective amount of a composition comprising:
(A) a compound of the formula:
where R
1
is a straight-chain perfluoroalkyl group or a partially fluorinated straight-chain alkyl group and R is a phenyl group or a substituted phenyl group having at least one substituent, wherein the substituent is selected from the group consisting of amino, formyl, halo, alkyl, alkoxy, haloalkyl, haloalkoxy, and nitro; and
(B) a suitable carrier therefor.
DESCRIPTION OF THE PREFERRED EMBODIMENTS
The present invention is directed to the use of 2-aryl-4,4-bis(trifluoromethyl)-6-fluoroalkyl-4H-1,3,5-oxadiazines having the structural formula:
wherein R is an aryl (group, optionally substituted with one or more groups chosen independently from amino, formyl, halo (i.e., fluoro, chloro, or bromo), alkyl, alkoxy, haloalkyl, haloalkoxy or nitro, and R
1
is a straight-chain perfluoroalkyl group or a partially fluorinated straight-chain alkyl group.
The compounds employed in the practice of the present invention can be made by the action of an aryl cyanide of formula RCN, where R is as above defined, with a fluorinated alkylidene amide of formula (CF
3
)
2
C═NCOR
1
, where R
1
is as above defined, in a solvent, such as diethyl ether, allowing the reaction mixture to stand for several hours without heating, then removing the solvent and purifying the product by distillation, chromatography, or crystallization, as appropriate.
The chemical compounds useful as pesticides are bis(4,4-trifluoromethyl)-4H-1,3,5-oxadiazines of the structural formula:
wherein R is a phenyl group, or a phenyl group independently substituted with one or more groups chosen from amino, formyl, halo (fluoro, chloro, or bromo), alkyl, alkoxy, haloalkyl, haloalkoxy, or nitro and R
1
is a straight-chain perfluoroalkyl group of from one to three carbon atoms, or a partially fluorinated straight-chain alkyl group. Where a substituent on the phenyl group, R, is alkyl, alkoxy, haloalkyl, or haloalkoxy, it is preferred that the alkyl moiety be a lower alkyl moiety, more preferably a lower alkyl of from one to four carbon atoms, e.g., methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, or tert-butyl, and most preferred that it be methyl.
Representative sets of values for such compounds are given in Table 1, where for clarity the substituents on the phenyl ring are separately specified as R
2
and R
3
.
TABLE 1
Cmpd#
R
1
R
2
R
3
1
CF
3
H
H
2
CF
3
4-Br
H
3
CF
3
2-F
H
4
CF
3
3-Cl
H
5
CF
3
4-Cl
H
6
CF
3
2-CF
3
H
7
CF
3
3-CF
3
H
8
CF
3
4-CF
3
O
H
9
CF
3
4-NH
2
H
10
CF
3
4-NO
2
H
11
CF
2
CF
3
H
H
12
CF
2
CF
3
2-Cl
H
13
CF
2
CF
3
3-Cl
H
14
CF
2
CF
3
3-CF
3
H
15
CF
2
CF
3
4-CF
3
H
16
CF
2
CF
3
4-CF
3
O
H
17
CF
2
CF
3
4-F
H
18
CF
2
CF
3
3-CF
3
5-CF
3
19
CF
2
CF
3
3-F
5-F
20
CF
2
CF
3
3-Cl
4-F
21
CF
2
CF
3
3-Cl
5-Cl
22
CF
2
CF
3
3-CH
3
H
23
CF
2
CF
3
3-CH
3
O
H
24
CF
2
CF
3
4-Cl
H
25
CF
2
CF
3
4-Br
H
26
CF
2
CF
2
CF
3
3-Cl
H
27
CF
2
CF
2
CF
3
4-Br
H
28
CF
2
CF
2
CF
3
4-F
H
29
CF
2
CF
2
CF
3
3-CF
3
H
30
CF
2
CF
2
CF
3
4-CH
3
H
31
CF
2
CF
2
CF
3
4-CHO
H
32
CHF
2
3-CF
3
H
33
CHF
2
4-CF
3
H
Chemicals of the foregoing, class include:
1 2-phenyl-4,4,6-tris(trifluoromethyl)-4H-1,3,5-oxadiazine;
2 2-(4-bromophenyl)-4,4,6-tris(trifluoromethyl)-4H-1,3,5-oxadiazine;
3 2-(2-fluorophenyl)-4,4,6-tris(trifluoromethyl)-4H-1,3,5-oxadiazine;
4 2-(3-chlorophenyl)-4,4,6-tris(trifluoromethyl)-4H-1,3,5-oxadiazine,
5 2-(4-chlorophenyl)-4,4,6-tris(trifluoromethyl)-4H-1,3,5-oxadiazine;
6 2,4,4-tris(trifluoromethyl)-6-{(2-trifluoromethyl)phenyl}-4H-1,3,5-oxadiazine;
7 2,4,4-tris(trifluoromethyl)-6-{(3-trifluoromethyl)phenyl}-4H-1,3,5-oxadiazine;
8 2-{4-(trifluoromethoxy)phenyl}-4,4,6-tris(trifluoromethyl)-4H-1,3,5-oxadiazine;
9 2-(4-aminophenyl)-4,4,6-tris(trifluoromethyl)-4H-1,3,5-oxadiazine;
10 2-(4-nitrophenyl)-4,4,6-tris(trifluoromethyl)-4H-1,3,5-oxadiazine;
11 2-(pentafluoroethyl)-6-phenyl-4,4-bis(trifluoromethyl)-4H-1,3,5-oxadiazine;
12 2-(2-chlorophenyl)-6-(pentafluoroethyl)-4,4-bis(trifluoromethyl)-4H-1,3,5-oxadiazine;
13 2-(3-chlorophenyl)-6-(pentafluoroethyl)-4,4-bis(trifluoromethyl)-4H-1,3,5-oxadiazine;
14 2-(pentafluoroethyl)-4,4-bis(trifluoromethyl)-6-{(3-trifluoromethyl)phenyl}-4H-1,3,5-oxadiazine;
15 2-(pentafluoroethlyl)-4,4-bis(trifluoromethyl)-6-{4-trifluoromethyl)phenyl}-4H-1,3,5-oxadiazine;
16 2-(pentafluoroethyl)-6-{(4-trifluoromethoxy)phenyl}-4,4-bis(trifluoromethyl)-4H-1,3,5-oxadiazine;
17 2-(4-fluorophenyl)-6-(pentafluoroethyl

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