Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Phosphorus containing other than solely as part of an...
Reexamination Certificate
2000-08-31
2003-01-07
Pryor, Alton N (Department: 1616)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Phosphorus containing other than solely as part of an...
C514S183000, C514S269000
Reexamination Certificate
active
06503891
ABSTRACT:
BACKGROUND OF INVENTION
This invention relates to stable, water-emulsifiable compositions of O,O-diethyl-O-(2-isopropyl-4-methyl-6-pyrimidinyl)phosphorothioate (DIAZINON insecticide), S-[1,2-bis(ethoxycarbonyl)ethyl]O,O-dimethylphosphorodithioate (MALATHION insecticide), or endosulfan and an organic carbonate solvent. More particularly, this invention relates to compositions containing, as the organic carbonate, alkylene carbonate or dialkyl carbonate or both.
Xylene, kerosene, and cyclohexanone have been used as solvents in agricultural formulations containing O,O-diethyl-O-(2-isopropyl-4-methyl-6-pyrimidinyl)phosphorothioate, S-[1,2-bis(ethoxycarbonyl)ethyl]O, O-dimethylphosphorodithioate, or endosulfan. These solvents, however, are believed to be toxic to humans, high volatility, high flash point, and/or poor biodegradability. Due to the deficiencies and disadvantages of conventional compositions that contain these solvents in combination with O,O-diethyl-O-(2-isopropyl-4-methyl-6-pyrimidinyl)phosphorothioate, S-[1,2-bis(ethoxycarbonyl)ethyl]O,O-dimethylphosphorodithioate, or endosulfan, new compositions are highly desirable.
SUMMARY OF INVENTION
The invention provides a solution to one or more of the problems and disadvantages discussed above.
In one broad respect, this invention is a composition comprising an organic carbonate and O,O-diethyl-O-(2-isopropyl-4-methyl-6-pyrimidinyl)phosphorothioate, S-[1,2-bis(ethoxycarbonyl)ethyl]O,O-dimethylphosphorodithioate, or 6,7,8,9,10, 10-hexachloro-1,5,5a,6,9,9a-hexahydro-6,9-methano-2,4,3 -benzodioxathiepin-3-oxide. The organic carbonate and the O,O-diethyl-O-(2-isopropyl-4-methyl-6-pyrimidinyl)phosphorothioate, S-[1,2-bis(ethoxycarbonyl)ethyl]O,O-dimethylphosphorodithioate, or 6,7,8,9,10, 10-hexachloro-1,5,5a,6,9,9a-hexahydro-6,9-methano-2,4,3-benzodioxathiepin-3-oxide may be present in amounts effective to form a water emulsifiable composition. Generally, the amount of the organic carbonate in the composition may vary from about 5 percent by weight to about 95 percent by weight, based on the total weight of the composition. Generally, the amount of O,O-diethyl-O-(2-isopropyl-4-methyl-6-pyrimidinyl)phosphorothioate, S-[1,2-bis(ethoxycarbonyl)ethyl]O,O-dimethylphosphorodithioate, or 6,7,8,9,10, 10-hexachloro-1,5,5a,6,9,9a-hexahydro-6,9-methano-2,4,3-benzodioxathiepin-3-oxide may vary from about 95 percent by weight to about 5 percent by weight, based on the total weight of the composition. 0,0-diethyl-0-(2-isopropyl-4-methyl-6-pyrimidinyl)phosphorothioate is available commercially under the name DIAZINON. S-[1,2-bis(ethoxycarbonyl)ethyl]O, O-dimethylphosphorodithioate is available commercially under the name MALATHION. 6,7,8,9,10,1 0-hexachloro- 1,5,5a,6,9,9a-hexahydro-6,9-methano-2,4,3-benzodioxathiepin-3-oxide is also known as endosulfan. The composition may also include a co-solvent, a surfactant, an emulsifier, or combination thereof.
In another broad respect, this invention is a process for forming a composition of O,O-diethyl-O-(2-isopropyl-4-methyl-6-pyrimidinyl)phosphorothioate, S-[1,2-bis(ethoxycarbonyl)ethyl]O,O-dimethylphosphorodithioate, or endosulfan, comprising: combining the O,O-diethyl-O-(2-isopropyl-4-methyl-6-pyrimidinyl)phosphorothioate, S-[1,2-bis(ethoxycarbonyl)ethyl]O,O-dimethylphosphorodithioate, or endosulfan with an organic carbonate. In one aspect, this process may also include the addition of water to form an emulsion. The emulsion may then be sprayed by the end user, such as being sprayed on crops.
In another broad respect, this invention is a method of supplying an organic carbonate for use in insecticide compositions, comprising: providing the organic carbonate for a permitted use in formulations comprising an insecticide and an organic carbonate. If necessary, decisions may be appealed to the courts in the United States. The formulations are as described herein and may include other insecticides, herbicides, pesticides, and other agriculturally active compounds apart from diazinon, malathion, and endosulfan, and may include other cosolvents and/or other components.
This composition may be used by applying it to an area to be treated for a given insect. The amount of insecticide may vary in accordance with known principles. O,O-diethyl-O-(2-isopropyl4-methyl-6-pyrimidinyl)phosphorothioate, S-[1,2-bis(ethoxycarbonyl)ethyl]O,O-dimethylphosphorodithioate, and endosulfan are known insecticides. The application is generally performed by mixing the composition with water to form an emulsion. This invention in another broad respect is a process useful for applying an insecticide composition, comprising: mixing water and an insecticide composition to form an emulsion, and applying the emulsion on a surface, wherein the insecticide composition comprises an organic carbonate and O,O-diethyl-O-(2-isopropyl-4-methyl-6-pyrimidinyl)phosphorothioate, S-[1,2-bis(ethoxycarbonyl)ethyl]O, O-dimethylphosphorodithioate, or 6,7,8,9,10,10-hexachloro- 1,5,5a,6,9 ,9a-hexahydro-6,9-methano-2,4,3-benzodioxathiepin-3-oxide. The emulsion may be applied in a variety of well known ways, such as by spraying. The surfaces to be treated may vary widely, such as on the ground, dirt, rock, lumber, plants, lawns, trees, in and around buildings, and other surfaces that are treated with these insecticides conventionally.
This invention has a number of advantages. For example, the compositions have several important attributes, including low toxicity, high flash point, good biodegradability of the transport system (the organic carbonate, other solvent(s), and any surfactant). It has further been advantageously found that the compositions may be blended with additional co-solvents, activators, and the like, or may be used directly. Furthermore, in the case of propylene carbonate, the propylene carbonate breaks down into propylene glycol, which is non-toxic. Hence, the propylene carbonate compositions of this invention are environmentally friendly, particularly as compared to aromatic hydrocarbons previously used to form compositions with the In another broad respect, this invention is a process for forming a concentrated composition of O,O-diethyl-O-(2isopropyl4-methyl-6-pyrimidinyl)phosphorothioate, S-[1,2-bis(ethoxycarbonyl)ethyl]O, dimethylphosphorodithioate, or endosulfan. The compositions of this invention may advantageously be of low volatility and free of carcinogenic chemicals. Advantageously, the compositions may be formulated into water emulsifiable concentrates. Likewise, the compositions may be formulated to contain the same amount of active ingredient (O,O-diethyl-O-(2-isopropyl4-methyl-6-pyrimidinyl)phosphorothioate, S-[1,2-bis(ethoxycarbonyl)ethyl]O,O-dimethylphosphorodithioate, or endosulfan) per gallon as in presently registered commercial formulations. Advantageously, when diluted with water, the formulations of the present invention may have less than 1 percent solids fallout after 1 hour when subjected to an accelerated stability test at 50 degrees Centigrade.
DETAILED DESCRIPTION OF THE INVENTION
The compositions of this invention contain a carbonate such as alkylene carbonate or dialkyl carbonate or both.
The organic carbonates that may be employed in the practice of this invention include alkylene carbonates (cyclic compounds) and dialkyl carbonates. In general, the organic carbonates contain a low number of carbon atoms. The alkylene carbonate used in the present invention can contain from 2 to 10 carbon atoms. Representative examples of alkylene carbonates that may be employed in the practice of this invention include ethylene carbonate and propylene carbonate. Mixtures of carbonates may also be employed. In the practice of this invention, alkylene carbonates are preferred, and among the alkylene carbonates propylene carbonate is preferred. The dialkyl carbonate used in the present invention may contain from 3 to 25 carbon atoms. The dialkyl carbonate may be of formula R—CO
3
—R′, w
Klein Howard P.
Marquis Edward T.
Speranza George P.
Huntsman Petrochemical Corporation
O'Keefe Egan & Peterman, LLP
Pryor Alton N
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