Drug – bio-affecting and body treating compositions – Preparations characterized by special physical form – Biocides; animal or insect repellents or attractants
Reexamination Certificate
2001-07-25
2003-04-29
Richter, Johann (Department: 1621)
Drug, bio-affecting and body treating compositions
Preparations characterized by special physical form
Biocides; animal or insect repellents or attractants
C562S571000, C554S110000
Reexamination Certificate
active
06555120
ABSTRACT:
FIELD
This invention is related to host marking pheromones (HMPs) also known as oviposition deterring pheromones (ODPs) in insects. In particular it refers to host marking pheromones in fruit flies of the genus Anastrepha.
BACKGROUND
Fruit flies (Diptera: Tephritidae) are considered among the most economically important pests worldwide (Aluja and Liedo 1993; McPheron and Steck 1996). The most notorious pestiferous species belong to the genera Anastrepha, Bactrocera, Ceratitis, Rhagoletis, and Toxotrypana (Aluja 1993). Among the 184 reported species of Anastrepha (Aluja 1994), seven stand out because of the damage they cause to commercially grown fruit:
A. fraterculus, A. grandis, A. ludens, A. obliqua, A. serpentina, A. striata
and
A. suspensa
. Distribution and fruit species attacked are indicated in TABLE 1 (from Hernandez-Ortiz and Aluja 1993).
TABLE 1
Distribution and most common hosts of the seven economically
important Anastrepha species.
Commercially grown fruit
Anastrepha species
Distribution
species attacked
A. fraterculus
Mexico to Argentina
Guava, Oranges
A. grandis
South America
Commercially grown
cucurbits
A. ludens
Southern USA to
Oranges, Mango,
Costa Rica
Grapefruit
A. obligua
Mexico to Argentina
Mango, Tropical Plums
A. serpentina
Mexico to Argentina
Mammee Apple, Chico
Zapote
A. striata
Mexico to Argentina
Guava
A. suspensa
Florida and Caribbean
Grapefruit, Guava
Islands
Damage of these fly species is direct (larvae in fruit) and indirect (severe quarantine restrictions that limit international commerce). Infestation level (i.e., percent infested [=lost] fruit in a tree can vary between zero and 90% depending on the fruit growing region, fruit species or cultivar, size of fruit fly population, management intensity in orchard and degree of capitalization of orchard owner. Control of these pests has been historically attempted through fumigants, toxic bait sprays (a food-based bait mixed with-an insecticide) and on occasion by use of the sterile insect technique (SIT) (reviewed by Steiner 1955 and Aluja 1994). Despite being quite effective, the large scale use of toxic bait sprays is no longer acceptable because of the negative impact on beneficial and native entomofauna (Asquith and Messing 1992, Hölmer and Dahlsten 1993 and references therein). In recent years, a number of alternatives such as the use of gibberelic acid to enhance the innate resistance of citrus to fly attack (Greany 1989), insect growth regulators such as cyromazine (Moreno et al. 1994), pathogens such as
Bacillus thuringiensis
Berliner (Martinez et al. 1997) and photoactivated dyes as for example SureDye
M.R.
(PhotoDye International, Inc., Boca Raton, USA) are being explored. Despite their promise as viable alternatives to toxic bait sprays, some of these methods could still prove unacceptable because of the deleterious effect on nontarget insects (Aluja 1996). The latter, because the killing agent needs to be ingested by the adult insect. The only practical way of achieving this is by mixing it with a food-based bait. As is the case with food-based baits mixed with an insecticide, lures used in combination with photoactivated dyes or insect growth regulators are non-specific. That is, they attract a large, number of nontarget insects (such as many species of insects in the order Diptera) which are also killed.
A highly selective alternative to the use of insecticides that has been recently tested in fruit flies of the genus Rhagoletis, and that does not require a bait to be effective, is the use of synthetic host marking pheromones (HMPs). HMPs are deposited by flies on the surf ace of a fruit after an egglaying bout and given a large enough concentration deter conspecifics from ovipositing in the same fruit (Katsoyannos and Boller 1980). Based on this knowledge and chemical work by Hurter et al. (1987a; 1987b) and Ernst and Wagner (1989), it was possible to successfully test the synthetic HMP of
Rhagoletis cerasi
as a fruit-infestation-reducing-agent in commercial cherry orchards in Switzerland (Aluja and Boller 1992a; 1992b). Application of synthetic HMP to the entire tree crown reduced the number of larvae per kg of fruit by a factor of 10 when compared with an untreated tree (0.226 vs. 0.021 pupae/fruit) in untreated and treated trees, respectively. A significant reduction.in fruit infestation could also be achieved when only one half (top to bottom) of the tree crown was treated (Aluja and Boller 1992b). Of significance here, is the fact that host marking behavior has been also reported in several Anastrepha species:
A. suspensa
(Prokopy et al., 1977),
A. fraterculus
(Prokopy et al. 1982),
A. sororcula
and
A. obliqua
(Simoes et al. 1978),
A. pseudoparallela
(Polloni and Da Silva 1986),
A. striata
(Aluja et al. 1993),
A. bistrigata
(Gomes -Da Silva 1991),
A. grandis
(Selivon 1991) and
A. ludens
(Papaj and Aluja 1993). As was the case with Hurter and collaborators (Hurter et al. 1987b), when working with
R. cerasi
, Santiago and collaborators (1990; 1991) demonstrated that the feces of
A. ludens
and
A. serpentina
contained a HMP. Using thin-layer chromatography, they further showed that one band provoked the deterrent effect. They also were able to show that crude feces extracts of
A. ludens
applied to fruit-bearing mango tree branches, reduced the level of infestation by
A. ludens
(Santiago et al. 1991). In general, host marking pheromones, given a high enough concentration, deter oviposition in fruit by fruit fly females (Averill and Prokopy 1989).
There remains a need in the art for a highly selective (i.e., directed only at flies in the genus Anastrepha) and environmentally-friendly alternative to the use of Anastrepha control methods that is not dependent on a food-based bait to deliver the toxicant or killing agent. The present invention describes several substances that reduce the damage inflicted to fruit of.value to humans by flies in the genus Anastrepha and that does not require a food-based bait to be delivered or to be effective.
SUMMARY
According to the present invention it has been found that 2-(2′, 14′-Dimethyl-pentadecanoylamino)-pentanedioic acid of the formula (I),
isolated from the feces of
Anastrepha ludens
, functions as an oviposition deterrent against economically and non-economically important fruit flies (Diptera: Tephritidae) of the genus Anastrepha. This is significant because the above mentioned substance if properly formulated, can henceforth be used to reduce the damage these insects inflict on fruit grown in commercial and semi-commercial orchards, in backyard gardens or in single trees planted in residential gardens. The present invention relates to a method for the isolation of the host marking pheromone (oviposition deterring pheromone) of
Anastrepha ludens
which is applicable to all species of fruit flies of the genus Anastrepha. The invention also relates to a method for the synthesis of oviposition deterrents which have the general formula (II)
Where R1 is H, C1-C4 alkyl, C3-C6 cycloalkyl, C3- or C4 alkenyl, C3- or C4 alkynyl;
R2 and R3 independent of one another are H or C1-C4 alkyl, C3-C6 cycloalkyl, C3- or C4 alkenyl, C3- or C4 alkynyl, benzyl or benzyl which is substituted once to three times on the phenyl ring by halogen, C1-C4 alkyl;
R4 is H or C1-C4 alkyl, C3-C6 cycloalkyl, C3- or C4 alkenyl, C3- or C4 alkynyl, C1-C4 alkyl carbonyl, benzyl or benzyl which is substituted once to three times on the phenyl ring by halogen, C1-C4 alkyl,
Where &agr; refers to (R) or (S) stereoisomers (or their mixtures), with the premise that R1 is not=H.
Where n=an integer between 0 and 15.
Where * refers to (L) or (D) amino acid stereochemistry (or their mixtures).
The alkyl, alkenyl and alkynyl groups in the above definitions can be straight chain or branched. Alkyl groups for example are methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, iso-butyl, and tert-butyl.
Examples of alkenyls are vinyl, allyl, methallyl, 1-methylvinyl, but-2-en-1-yl.
The cycloalkyl radicals which
Aluja-Schuneman Martin Ramon
Diaz-Fleischer Francisco
Edmunds Andrew J. F.
Hagmann Leonhard
Instituto de Ecologia, A.C.
Keefer Timothy J.
Richter Johann
Zucker Paul A.
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