Use of flavonoid and aromatic aldehydes as pesticides

Details Use of flavonoid and aromatic aldehydes as pesticides Use of flavonoid and aromatic aldehydes as pesticides

1995-06-07

2001-06-26

Levy, Neil S. (Department: 1616)

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Aldehyde doai

C514S693000, C424S405000, C424S406000, C424S407000

Reexamination Certificate

active

06251951

ABSTRACT:

INTRODUCTION
1. Technical Field
The present invention is related to the biocontrol of plant pathogens through nutritional mediation. The invention is exemplified by the use of cinnamic aldehyde and coniferyl aldehyde to control growth of fungi and parasitic insects, including sap sucking insects which colonize the surfaces of plant parts and tissues.
2. Background
The surfaces of plant parts such as roots and leaves are colonized by a variety of organisms, many of which are dependent upon the host plant as a source of nutrients. The colonizing organisms include pathogenic fungi and sap-sucking insects; both groups are capable of inflicting severe damage to the host plant, including stunting the growth of the host plant and decreasing plant productivity, to killing the host plant.
Fungi pathogenic for plants are many and diverse. They occur in most groups of fungi. A few, such as rusts, Uredinales, and powdery mildew and downy mildew, Erysiphacea and Peronosporacea, are obligate parasites. Generally, a particular rust or mildew is associated with specific host plants which elaborate nutrients required by the pathogen. As an example, rust, caused by
Phragmidrium mucronatrum
, is an important fungal disease associated with roses; it produces bright orange pustules on the underside of rose leaves and pale yellow spots on the top. Powdery mildew, caused by
Sphaerotheca pannosa
(Wallr. ex. Fr.) Lev var. rosae Woronichine also is associated with roses and is probably the most widely distributed and serious disease of glasshouse, garden, and field-grown roses alike.
Pathogenic insects which infest plants include those insect species which are symbiotic with bacteria, such as aphids, leaf hoppers, and white fly; the host insect cannot survive without the symbionts. As an example, aphids (homoptera) possess symbiotic bacteria of the genus Buchnera in cells called mycetocytes within the hemocoel. The bacteria are transmitted directly from the maternal aphid to her offspring and aposymbiotic aphids do not occur naturally. The bacteria may provide lipids which are required for embryogenesis of the host insect but which are absent or in low concentrations in phloem sap in plants infected by the insects.
The plant pathogens include the grape phylloxera (
Daktulosphaira vitifoliae
), an aphid-like insect, and nematodes. Phylloxera is native to the United States east of the Rocky Mountains, where it lives on native wild species of grapes, which have evolved resistance to the feeding of the insect. The European grape (
Vitis vinifera
), which is used to produce wine, evolved in western Asia and has no resistance to phylloxera. Stem and bulb nematode (
Ditylenchus dipsaci
) has been recorded from all the major agricultural regions in California This wide distribution probably reflects its spread on such infested planting material as garlic cloves. Wherever such infested material is grown, the nematode may be introduced.
Ditylenchus dipsaci
can be found parasitizing a wide range of cultivated and wild plants. Nematodea produce galls in infected tissue. In addition to the disturbance caused to plants by the nematode galls themselves, damage to infected plants is increased by certain parasitic fungi, which can easily attach the weakened root tissues and the hypertrophid, undifferentiated cells of the galls. Moreover, some fungi, for example, Pythrium, Fusarium, and Rhizoctonia, grow and reproduce much faster in the galls than in other areas of the root, thus inducing an earlier breakdown of the root tissues.
A variety of pesticide compositions are used for controlling plant pathogens. For example, protective fungicidal sprays on a 6-7 day schedule for both rust and powdery mildew when environmental conditions favor disease development are the typical means of control. Two frequently used systemic fungicides are benomyl and triforine. However, the cost of fungicides for control of powdery mildew is high: in cut rose crops the cost of treatment in the State of California is several million dollars a year.
The older fungicides include inorganic compounds such as copper and sulphur and the organic protectants such as thiram, captam, maneb, and chlorotholonil. These compounds act only at the surface of the plant and must be present at or before appearance of the fungal pathogen in order to prevent infection. These older fungicides are multisite inhibitors; i.e., they affect many metabolic activities in a fungus. The newer fungicides tend to be highly effective organic systemics such as benzimididazoles, sterol biosynthesis inhibitors, carboxanilides, and phenylamides which act internally as well as at the plant surface. In contrast to the older surface protectants, the systemic fungicides are generally effective at much lower dosages and can cure established fungal infections, a critical factor in disease management. The systemic fungicides usually act at a single target site in the fungus, interfering with specific metabolic processes that are necessary for production of all new cell material required for growth, maintenance, and virulence of the fungal organism. These preparations typically are effective only against fungal pathogens.
Current methods of chemical control for certain above-ground pests (e.g., spider mite, aphids, silverleaf white fly, leaf hoppers) include those which combine two insecticides from different chemical classes, for example, combining a synthetic pyrethroid with an organophosphate or organochlorine insecticide. Soil fumigants have been a popular treatment for soil pests (nematodes, phylloxera). Use of certain highly effective types of insecticides and fumigants has sharply decreased in recent years due to cancellations of public regulatory agency registrations, or refusals of re-registrations, of products.
The wide-spread use of pesticides has resulted in the development and evolution of resistant pathogens, as well as growing environmental and health care concerns. A highly visible ecological-environmental activist community and public regulatory agencies have resulted in fewer and fewer pesticide registrations and, consequently, less related research and development.
The use of flavonoid and aromatic aldehydes for treatment of both fungal and other pathogens has been reported. However the preparations used have been reported to require the use of expensive antioxidants, and at the concentrations used, would be expected to be phytotoxic to the host plant. Such formulations also are reported to require multiple applications to ensure continued protection of the host plant. It therefore is of interest to identify and/or develop, “biorational” fungicides which have lower animal and environmental toxicities and which also do not exhibit significant phytotoxicity at the concentrations used to control pathogenic fungi and insects.
3. Relevant literature
A method of protecting crops from attack of insect pests, microorganisms and pathogenic microbes using a composition comprising cinnamic aldehyde and requiring an antioxidant is disclosed in U.S. Pat. No. 4,978,686. Protection of crops against pathogenic microorganisms and insect pests by applying an aqueous composition containing a cinnamaldehyde is disclosed in French patent application 2529755. U.S. Pat. No. 2,465,854 describes an insecticidal composition containing a cinnamic aldehyde derivative. Control of Verticillium using cinnamaldehyde in the substrate in which mushrooms are grown is disclosed in U.S. Pat. No. 5,149,715.
Reweri, et al. describe induction of systemic resistance to powdery mildew in cucumber by phosphates.
Biol. Agic. and Hort
. (1993) 9:305-315. Horst and Kawamato disclose the effect of sodium bicarbonate and oils on the control of powdery mildew and black spot on roses.
Plant Disease
, March 1992, p.247. Sodium bicarbonate and severely solvent refined light paraffinic petroleum oil have been used to control black spot and powdery mildew. Ziv et al.,
Hort. Science
(1993) 28:124-126.
Elad et al. disclose the effect of film-forming polymers on powdery mildew of cucumber.
Phytoparasitica
(1989),

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