Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Reexamination Certificate
2002-03-11
2004-04-13
Pryor, Alton N. (Department: 1616)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
C514S461000, C514S372000
Reexamination Certificate
active
06720352
ABSTRACT:
This application claims the benefit of PCT/US00/08849, which, in turn claims the benefit of South African provisional application No 98/10240, filed May 10, 1999.
TECHNICAL FIELD
This invention relates to novel compositions of aldehydes and isothiocyanates and their use for the enhancement of crop production, and more particularly to compositions of furfural or substituted furfurals and hydrocarbon isothiocyanates or substituted hydrocarbon isothiocyanates and their use for the control of phytoparasitic nematodes.
BACKGROUND ART
Most of the food produced in the world for human and animal consumption is grown from farm crops. As the population of the world increases it is becoming increasingly more difficult to produce adequate quantities of agricultural products to satisfy worldwide consumption demand. The situation is already critical because there is a limited amount of available arable land, and is becoming more and more critical each year as valuable farmland in the United States and other major crop-producing countries is converted to residential or industrial use.
Further aggravating the problem is the fact that plant pests, such as fungi, insects and nematodes destroy vast quantities of the plant crops. For example, it is estimated that in the tropic and subtropic regions of the world, plant-parasitic nematodes destroy up to fifty percent or more of the sprouts that are planted each year by feeding on the plants and/or infecting the plants with harmful diseases. Nematodes attack a wide variety of agricultural crops, such as soybeans, peanuts, strawberries, cotton, tobacco, squash, potatoes and other root vegetables, etc.
Because of the limited supply of fertile land, it is imperative that the productivity of existing farmland be increased. One way of accomplishing this is to reduce crop losses caused by plant pests by the use of biocides. Rodriguez-kabana, R., et al., in “Chemical and Biological Control”,
Soilbome Diseases of Tropical Crops
, 1997, Chap. 17, pp. 397-418, present a history of plant pathogen control by treatment of pest-containing soil with chemical biocides. According to the authors, chemical treatment of crops for pest control has been practiced since the nineteenth century. Early biocides include carbon disulfide, formaldehyde and trichloronitromethane (chloropicrin). Later developed, more highly effective pesticides include halogenated hydrocarbons, such as methyl bromide, ethylene dibromide (EDB), and 1,2-dibromo-3-chloropropane (DBCP). EDB and DBCP have been banned for use as pesticides in several industrialized countries because of their carcinogenicity or mutagenicity, and methyl bromide has been scheduled for removal from the market in the United States because of its harmful effect on the ozone layer.
Moje, W, “The Chemistry and Nematocidal Activity of Organic Halides”,
Advances in Pest Control Research
, Vol III, 1960, pp. 181-212, describes isothiocyanates as effective against nematodes and other soil-inhabiting organisms (pp. 207-209).
More recently, aldehydes, such as furfural, benzaldehyde and citral have been described as useful for plant pathogen control. For example, U.S. Pat. No. 5,084,477 discloses the use of furfural as a nematicide.
Compositions of aldehydes and various chemical compounds have been used for a variety of applications. German Patent No. 448, 446 discloses the use of water-soluble furfural and a respiratory or contact poison, such as pyrethrum or nicotine extract as an agent for combating insect plant pests; U.S. Pat. No. 4,440,783 discloses the use of a combination of allyl isothiocyanate or lower alkyl isothiocyanates with lemon grass oil and/or an odor masking agent, which may be benzaldehyde, to repel animals from garbage; and U. S. Pat. No. 5,703,124 discloses and antimicrobial composition comprising allyl isothiocyanate and a polyhydric alcohol which may contain aldehyde groups, the polyhydric alcohol enhancing the water solubility of the allyl isothiocyanate. Japanese Patent No. 11269010, issued Oct. 5, 1999 and reported in Chemical Abstract No. 1999:629918, discloses compositions comprised of a substituted glyoxylohydroximoyl chloride, an antifungal agent, which may be glutaraldehyde, and an antibacterial agent, which may be an alkylene bis(isothiocyanate). These compositions were found to control bacteria and fungi in white water in paper manufacturing. Farghally et al., in J. Pharm. Belg. (1985), 40(6), 366-72 report the synthesis of selected quinolinecarboxyaldehyde hydrazone derivatives by the reaction of quinolinecarboxyaldehyde hydrazones with, for example, phenylisothiocyanate (Chemical Abstract No. 1987:84461). The synthesized compounds were found to have no antibacterial activity. U.S. Pat. No. 6,051,233 discloses the use of compositions containing mustard oil, including allyl isothiocyanate, for soil treatment. These compositions additionally contain a heat component which may be, for example cinnamic aldehyde or benzaldehyde.
There is a continuing need to find more effective plant pathogen control agents. This invention provides new compositions that are highly effective as nematicidal agents.
DISCLOSURE OF INVENTION
According to a first broad embodiment, the invention comprises a composition comprised of (a) at least one heterocyclic aldehyde containing 4 to 25 carbon atoms, and (b) at least one isothiocyanate containing 2 to 18 carbon atoms or precursor thereof.
In a preferred aspect of the first embodiment, the least one heterocyclic aldehyde contains 4 to 12 carbon atoms and said at least one isothiocyanate or precursor thereof comprises an aliphatic isothiocyanate containing 2 to 14 carbon atoms, a precursor of an aliphatic isothiocyanate containing 2 to 14 carbon atoms, a cyclic isothiocyanate containing 5 to 12 carbon atoms, a precursor of a cyclic isothiocyanate containing 5 to 12 carbon atoms or mixtures thereof.
In another preferred aspect of the first embodiment, the at least one heterocyclic aldehyde contains oxygen, nitrogen, sulfur, phosphorus or combinations thereof, the at least one isothiocyanate or precursor thereof additionally contains oxygen, phosphorus, additional nitrogen, additional sulfur, or combinations thereof, or the heterocyclic aldehyde contains oxygen, nitrogen, sulfur, phosphorus or combinations thereof and the isothiocyanate or precursor thereof contains oxygen, phosphorus, additional nitrogen, additional sulfur, or combinations thereof.
In another preferred aspect of the first embodiment, the heterocyclic aldehyde is a formyl cyclic ether.
In another preferred aspect of the first embodiment, the at least one heterocyclic aldehyde comprises furfural, 2,5, -diformyl furan, formyl pyran, formyl tetrahydrofuran, formyl pyridine, or mixtures thereof, and the at least one isothiocyanate or precursor thereof comprises methyl isothiocyanate, ethyl isothiocyanate, propyl isothiocyanate, butyl isothiocyanate, allyl isothiocyanate, phenyl isothiocyanate, benzyl isothiocyanate sodium N-methyidithiocarbamate, tetrahydro-3,5-dimethyl-2H-1,3,5-thiadiazin-2-thione or mixtures thereof.
In another more preferred aspect of the first embodiment, the at least one heterocyclic aldehyde thereof comprises furfural, 2,5,-diformyl furan, or mixtures thereof, and the at least one isothiocyanate or precursor thereof comprises methyl isothiocyanate, allyl isothiocyanate, sodium N-methyldithiocarbamate, tetrahydro-3,5-dimethyl-2H-1,3,5-thiadiazin-2-thione or mixtures thereof.
In another preferred aspect of this embodiment, the at least one isothiocyanate is present as a component of mustard oil.
In another preferred aspect of the first embodiment, the composition further comprises a carrier system for the heterocyclic aldehyde, the isothiocyanate or both the heterocyclic aldehyde and the isothiocyanate.
In another preferred aspect of the first embodiment, the composition is in the form of a solution, a suspension or an emulsion. Preferably, it is in the form of an aqueous solution, suspension or emulsion.
In another preferred aspect of the first embodiment, the composition further comprises an
Pryor Alton N.
Reap Coleman R.
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