Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Phosphorus containing other than solely as part of an...
Reexamination Certificate
1998-12-16
2001-03-13
Pak, John (Department: 1616)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Phosphorus containing other than solely as part of an...
C424S196110, C424S405000, C424SDIG001, C514S075000, C514S080000, C514S082000, C514S084000, C514S085000, C514S086000, C514S087000, C514S088000, C514S090000, C514S091000, C514S092000, C514S093000, C514S094000, C514S095000, C514S098000, C514S099000, C514S102000, C514S103000, C514S104000, C514S107000, C514S108000, C514S114000, C514S118000, C514S126000, C514S127000, C514S129000, C514S131000, C514S140000, C514S141000, C514S142000, C514S143000
Reexamination Certificate
active
06200961
ABSTRACT:
BACKGROUND OF THE INVENTION
1. Field of the Invention
The instant invention relates to bioefficaciously enhanced organophosphorous insecticidal formulations comprising the active and low volatile organic compound (low VOC) compositions; processes for preparing same; and methods of use.
2. Technology Description
Insecticides, miticides, aphicides, fungicides, bacteriocides, acaricides, nematicides (hereinafter these pesticides will be generically referred to for conciseness as “insecticides” as the term “insecticidally” will similarly represent generically miticidally, nematicidally, etc.) continue to be a group of products of immense agricultural and economic importance. Insecticides are expected to display ideal properties of a wide array including broad-spectrum activity concomitant with safety to beneficial insects, low mammalian and fish toxicity, and sufficiently long residual action yet with insignificant, harmless residue levels. In keeping with the above goals, it is desirable to utilize the minimum amount of insecticide necessary to achieve the required results. Therefore, formulation adjuvants that enhance the bioefficacy of the active and thus result in lower effective delivery amounts of the active to a locus are much sought after.
Many, if not most, insecticidal compounds are solid materials which have very low solubility in water. As a result, formulators are constantly using their ingenuity to find means for preparing these materials in stable formulations that can deliver maximum loading of active ingredient per unit volume to the end-user.
The most straight-forward approach to preparing concentrated liquid formulations with agrochemical actives, especially insecticides having limited aqueous solubility, has been through the use of aromatic organic solvent systems. In such systems, aromatic organic solvents such as xylene or kerosene are used to solubilize the pesticidal compound of interest.
Commonly, surfactants are also added to the insecticide-solvent compositions to form emulsions. The surfactant-emulsifiers interact with the insecticides in a number of ways both before and during actual use, i.e., application to the locus. The surfactants, often a pair of nonionic and anionic surfactants, can initially disperse and/or emulsify the insecticide in the solvent or in an inert carrier media and may also act as spreader, sticker, stabilizer, wetting agent, and defoamer. The surfactant composition may affect the rate of drying of a droplet on a surface and the nature of a residue liquid or crystal.
The presence of the volatile organic compounds in these formulations, together with the surfactants, enable stable emulsifiable insecticidal concentrates (EC's) to be prepared. Although such EC formulations have played and continue to play a major role in the insecticidal market, they have a significant drawback in that the formulations are commonly based on the use of considerable quantities of highly volatile organic compounds (high VOC's). These high VOC's create both toxicological and ecotoxicological problems. As a result, many government agencies such as the United States Environmental Protection Agency and the European Economic Community Council are proposing legislation and many countries such as Germany and Canada are now requiring eco-labeling of formulations which contain high VOC's.
Thus, to reduce not only the deleterious effects upon the environment, but also the potential for hazardous worker exposure situations, especially in closed environments such as greenhouses, agricultural/chemical manufacturers and formulators continually seek ways to deliver highly loaded, stable insecticidal formulations to the end-user with significantly reduced levels of high VOC's and preferably without their presence.
To avoid the use of high VOC's in certain pesticidal formulations and to obtain slightly increased pesticidal loadings, Lubetzky, et al. in EP publication numbers 669,078 and 670,113 have disclosed the use of rosin and rosin derivatives that are insoluble in water to “plasticize” certain pesticides and thus to prepare pesticidal emulsions in water (EW's) and emulsifiable concentrates (EC's).
Applicants, in copending Provisional Application Ser. No. 60/070,101 filed Dec. 30, 1997, the disclosure of which is hereby incorporated by reference, relates to the discovery of extremely stable, highly loaded water soluble, low VOC pesticidal emulsion concentrates comprising a) a pesticide having a melting point of 110° C. or less; b) an alkoxylated fatty acid and rosin acid composition having from greater than 25 to about 60 weight percent alkoxylated rosin acids and from about 40 to less than 75 weight percent alkoxylated fatty acids with about 9 to 20 alkoxy moieties per molecule of acid; and c) at least one nonionic surfactant. It was discovered that the aforedescribed ethoxylated acid compositions possess very unique solvent characteristics with respect to certain relatively water insoluble pesticides.
SUMMARY OF THE INVENTION
The instant invention relates to the discovery that certain alkoxylated fatty/rosin acid formulations can not only provide extremely stable, highly loaded solvent systems for specific organophosphorous insecticidal compounds, but that these formulations can also significantly enhance the bioefficacy of these insecticidal compounds.
DETAILED DESCRIPTION OF THE INVENTION
It has been discovered that not only do certain water-soluble fatty acid/rosin acid ethoxylate compositions possess unique solvent characteristics with respect to low melting organophosphorous insecticidal compounds, but also that these adjuvant compositions significantly enhance the bioefficacy of the organophosphorous active. A preferred method of preparing emulsion concentrates of these components is to melt the organophosphorous insecticide and dissolve same in the highly alkoxylated mixture of the fatty acids and rosin acids; preferably a tall oil mixture.
Organophosphorous compounds are antichlolinesterase chemicals which damage or destroy chlolinesterase, the enzyme required for nerve function in the animal body. Organophosphorous insecticides, owing primarily to their ester nature, offer fundamental advantages in that they can be easily degraded hydrolytically, enzymatically, or biologically.
Organophosphorous compounds including those disclosed in U.S. Pat. No. 3,244,586 and specifically those with a halogen substitution, are known to be extremely useful as insecticides and are especially adapted to be employed as active toxicants in compositions for the control of a number of mite, insect, bacterial, and fungal organisms, such as beetles, ticks, worms, aphids, flies, roaches, cattle grubs, screw worms, trash fish, snails, ascarids, nematodes, roundworms, and
Rhizoctonia solani
(a plant pathogenic fungus).
The organophosphorous insecticides of the instant invention are preferably the phosphorothioates, phosphorodithioates, phosphoroamidates, phosphoroamidothioates, and phosphonothioates which have melting points below about 120° C.
More preferably, the organophosphorous compounds are of the following formulas:
wherein X is each individually O or S;
R
1
is substituted or unsubstituted, branched or unbranched lower alkyl, aryl, or aralkyl;
R
2
is XR
1
or R
1
;
R
3
is XR
4
or NHR
5
;
R
4
is substituted or unsubstituted lower alkyl, lower alkylene, vinyl, aryl, aralkyl, cyanoaryl, carboalkoxyalkyl, alkoxyalkyl, alkoxyaryl, alkoxycarbonylalkyl, aminocarbonylalkyl, alkylcarbamoylalkyl, alkylthioalkyl, or alkylthioaryl;
R
5
is H, acetyl, or lower alkyl; and
R
6
is lower alkyl, dioxanyl, or thiodi-p-phenylene wherein, in the specification and claims of this disclosure “aryl” includes heteroaryl compounds and “substituted” includes halogen substitutions. Also, in the present specification and claims, the term “lower alkyl” and “lower alkoxy” refer to radicals of from 1 to 8 inclusive, carbon atoms.
Much more preferably, the aryl radicals are selected from the group consisting of substituted or unsubstituted phenyl, pyridinyl,
Kostka Stanley J.
Pan Rennan
Aquatrols Corporation of America, Inc.
Choi Frank
Pak John
Shedden John A.
LandOfFree
Concentrates of organophosphorous insecticides does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Concentrates of organophosphorous insecticides, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Concentrates of organophosphorous insecticides will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-2525788