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United States Patent (19) 11 Patent Number: 5,447,718 Aldrich Et Al

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United States Patent (19) 11 Patent Number: 5,447,718 Aldrich Et Al USOO5447718A United States Patent (19) 11 Patent Number: 5,447,718 Aldrich et al. 45 Date of Patent: Sep. 5, 1995 54 PHEROMONE COMPOSITIONS FOR Pentatomoid Sex Pheromones, Biologically Active ATTRACTING EUSCHISTUS SPP. NSECTS Natural Products: Potential Use in Agriculture, ACS 75 Inventors: Jeffrey R. Aldrich, College Park, Symposium Series No. 380, Cutler, H. G., (ed.), 1988, Md. Michael P. Hoffmann, Davis, pp. 417-431. Calif.; Jan P. Kochansky; William R. Aldrich, J. R., Ann. Rev. Entomol, vol. 33, (1988), pp. Lusby, both of Adelphi, Md.; Lloyd 21-238. T. Wilson, Woodland; Frank G. Byers, et al., Naturwissenschaften, vol. 75, (1988), pp. Zalom, Davis, both of Calif. 153-155. 73 Assignees: The United States of America as Baeckstrom, et al., Tetrahedron, vol. 44, No. 9, 1988), represented by the Secretary of pp. 2541-2548. Agriculture, Washington, D.C.; The Hoffmann, et al., (Calif. Agric., vol. 41, (1987), pp. 4-6. Regents of the University of Warner, “Conjugated Fatty Acids from Latex of Eu California, Oakland, Calif. phorbia Lathyris', Phytochemistry, vol. 20, pp. 89-91, 1981. 21 Appl. No.: 461,890 : (22 Filed: Jan. 8, 1990 Primary Examiner-Marianne M. Cintins Assistant Examiner-Russel Travers 51) Int. Cl. ............................................. A01N 25/00 52 U.S. Cl. ................................................ ...... 424/84 Attorney, Agent, or Firm-M. Howard Silverstein; 58) Field of Search .......................................... 424/84 Randall E. Deck; John D. Fado 56 References Cited 57 ABSTRACT U.S. PATENT DOCUMENTS Compositions and methods are provided for attracting 3,541,203 1/1970 Fogle et al. ........................... 424/7 and subsequently trapping and/or killing crop pests 3,866,349 2/1975 Meijer et al........................... 43/4 from the Euschistus species. Alkyl esters of (2E,4Z)- decadienoic acid as a chemical attractant pheromone OTHER PUBLICATIONS and, in combination with a trap or toxicant, provide an Lofgvist et al CA 107: 193069p 1987. efficient means for controlling these insects. Panizzi, et al., Florida Entomol., vol. 68, No. 1, (1985), pp. 184-214. Aldrich, J. R., “Chemistry and Biological Activity of 11 Claims, 3 Drawing Sheets U.S. Patent Sep. 5, 1995 Sheet 1 of 3 5.447,718 Figure 1 E. Conspersus MALE E. Conspersus FEMALE BLANK CONTROL 2 4 6 8 10 12 14 16 MINUTES U.S. Patent Sep. 5, 1995 Sheet 2 of 3 5,447,718 Figure 2 1 OO 111 90 8O 8 7O n-n-n-s-to 6O 5O 67 40 41 82 59 30 15 2O 1 O 12 139 O || || 2O 40 60 80 100 120 140 160 180 200 m/Z U.S. Patent Sep. 5, 1995 Sheet 3 of 3 5,447,718 Figure 3 ~-s-s-s-O N------O methyl (2E,4E)- methyl (2Z,4E)- decadienoate decadienoate ----->O ~~~~ O (E)-geranylacetone decanoic acid 5,447,718 1. 2 to region and year to year, further complicating moni PHEROMONE COMPOSITIONS FOR toring and control strategies. ATTRACTING EUSCHISTUS SPP, INSECTS Although the use of insecticides has increased the quality and quantity of crop yields, there are serious BACKGROUND OF THE INVENTION 5 disadvantages to the use of presently available insecti 1. Field of the Invention cides. The toxicity to humans and animals is high. Addi This invention relates to compositions and methods tionally, they are not readily degraded and may thus for attracting, trapping and/or killing crop pests from pollute the environment. Therefore, reducing or elimi nating the amount of toxic insecticides used in the man Euschistus species known as stink bugs. IO agement of insect pests is desirable. It is an object of the 1. Description of the Prior Art present invention to provide compositions and methods The genus Euschistus is the largest of the genera in by which the amounts of pesticide may be reduced or the so-called stink bug family Pentatomidae (order He eliminated in eradicating Euschistus species stink bugs. miptera: suborder Heteroptera). Over 60 Euschistus Attractant pheromones have recently been identified species have been described, including 18 from North 15 for several species of predatory and plant-feeding stink America. Several Euschistus species are among the bugs. F. Warnaar Phytochemistry, Vol. 20, (1981), pp. most common members of the family in the western 89-91) disclosed the mass spectra (MS) of methyl hemisphere and, to many people, these large brown (2E,4Z)-decadienoate and methyl (2E,4E)-decadieno insects are recognized as the stink bug. ate, both of which closely resemble the MS of the E. Euschistus adults are strong fliers and often migrate 20 conspersus male-specific compound. to a succession of maturing crops where they feed on Additionally, there has been reported a strong syner developing fruits or seeds. The immature bugs usually gism between methyl E,Z-2,4-decadienoate and chalco disperse from the initial point of attack, thereby spread gran at attracting the bark beetle, Pityogenes chalcogra ing the infestation. As with other kinds of stink bugs, phus Byers, et al., Naturwissenschaften, Vol. 75, Euschistus adults and immatures suck sap or oil through 25 (1988), pp. 153-155). The reference does not indicate a hypodermic-like mouthparts, thus inconspicuously utility for the attraction and/or management of insects damaging the most valuable portion of the crop. Their of the Euschistus species. feeding also indirectly reduces yield and seed quality by transmitting diseases. In the absence of food or with the SUMMARY OF THE INVENTION onset of winter, adults are able to hibernate and resume 30 A chemical attractant pheromone for Euschistus spe attack the following season. cies as well as methods for concentrating and destroy Various Euschistus species attack a wide range of ing these pests is provided. In one alternative embodi fruit, field crops, vegetables, and nutcrops. In the west ment the attractant could be used to monitor area levels ern United States the consperse stink bug, E. conspersus, of these pests. In another embodiment the attractant is a major pest of tomatoes and also causes "catfacing' 35 would be useful for concentrating these pests in early of apples, peaches, pears, grapes, and other fruits. Dur maturing "trap-crops' where they could be economi ing years of high E. conspersus populations, cotton and cally destroyed by limited insecticide application. Anal seed alfalfa yields in California have been seriously ogously, this chemical attractant could be applied to reduced. East of the Rocky Mountains three other Eus artificially create overwintering aggregations of adults chistus species are serious agricultural pests of field, that would then be destroyed, thus preventing spring vegetable, fruit, and nut crops: E. servus, the brown outbreaks. stink bug; E. variolarius, the onespotted stink bug; and E. tristigmus, the dusky stink bug. One or more of these BRIEF DESCRIPTION OF THE DRAWINGS Euschistus species frequently coexist with the green FIG. 1 shows the peak and elution time of the attrac stink bugs, Acrosternum hilare and Nezara viridula, to 45 tant pheromone obtained from aeration experiments. form a complex that, along with the corn earworm, is FIG. 2 is the mass spectrum and chemical structure of the most damaging of the soybean pod feeders in the methyl (2E,42) -decadienoate. southern U.S. Although stink bug damage to soybean is FIG. 3 shows the structure of some minor male less severe in more northerly regions of the U.S., the specific volatile components from Euschistus spp. widespread use of reduced tillage crop systems has 50 vastly increased the threat of E. servus and E. viriolarius DETALED DESCRIPTION OF THE to corn. This threat has arisen in fields under a soy INVENTION bean/corn or wheat/corn rotation because the brown EXAMPLE 1. and onespotted stink bugs overwinter in soybean and 55 Isolation of Pheromones. wheat stubble, then feed on emerging corn seedlings in Euschistus conspersus adults were collected near Da the spring. A single stink bug can cause irrevocable vis, California and reared in the laboratory at the UC damage to a corn plant in less than 24 hours. In Central Davis Entomology Department on sunflower seeds, and South America other species of Euschistus bugs are green beans, and water. Volatiles were trapped from important pests. For example, E. heros is one of the groups of 10-30 virgin adult males or females by coax three major stink bug pests of soybean in Brazil. ing the bugs into a ca. 1 liter glass column and drawing Outbreaks of Euschistus and other stink bugs are air by vacuum (100 ml/min) over the bugs through 30 difficult to control because the bugs can migrate into a mg of activated charcoal for 24 hr. Trapped volatiles field and irreversibly damage a crop before they are were washed from the filter in 200-300 ul of CH2Cl2 noticed. Population build-ups that go undetected my 65 and stored under nitrogen at -20° C. lead to infestations of later maturing crops or outbreaks In four months, four species of Euschistus stink bugs the following season. Moreover, several stink bug spe were caught in traps deployed at the Agricultural Re cies usually coexist at varying abundances from region search Center, Beltsville, Md.: E. servus, E. tristigmus, 5,447,718 3 4 E. variolarius, and E. politus. Field-collected adults and terx3.0 cm length), and suspended 7.0 cm from the top /or laboratory-reared adults of E. servus, E. tristigmus, of the trap. Traps were baited by applying either 1 pull or and E. politus were used for aeration experiments as for 10 ul of methyl (2E,4Z)-decadienoate in the septum, E. conspersus. In addition, specimens of E obscurus and followed by 100 ul of CH2Cl2; control traps lacked the E. ictericus were obtained from Florida and aerated for ester.
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