Cabbage looper

Muscalure 20, the pheromone of the housefly has been prepared from oleic acid or erucic acid, similarly (Z)-l 1-heneicosene 21, the synergist of muscalure was obtained [189]. The intermediate 22 for the pheromone of the Cabbage looper was prepared using (Z)-methyl-4-octenedioate [166bJ, that was obtained by partial ozonolysis of (Z,Z)-l,5-cyclooctadiene. Similarly disparlure 23, the sex attractant of the gypsy moth, has been synthesized by two successive crossed-couplings with (Z)-4-octene dioate [191],... 

Behavioral and Hormonal Chemicals. Sex pheromones, which attract pests to traps, are used effectively to control some insect pests, like the grape berry moth (46) and cabbage looper. With other Insect pests, sex pheromones have been effectively used to monitor the size of pest insect populations to determine when pesticide treatments should be made. 

Fig.i General biosynthetic pathways for the production of alcohol, aldehyde, and acetate ester pheromone components in female moths. Top production of saturated fatty acids. Middle production of monounsaturated fatty acids and limited chain shortening produces intermediate compounds that can be reduced to an alcohol. Aldehyde and acetate ester pheromones are produced by an oxidase and acetyl-transferase, respectively. Bottom biosynthetic pathway for the production of the acetate ester pheromone components in the cabbage looper moth, Trichoplusia ni. The CoA derivatives are reduced and acetylated to form the acetate esters. Additional pheromone components include 12 OAc and ll-12 OAc... 

FIGURE 2 Pheromone structures of the American cockroach (periplanone B), the brownbanded cockroach (supellapyrone), bark beetles (ipsdienol enantiomers), and the cabbage looper moth (six acetates). 

FIGURE 3 Pheromone biosynthetic pathways commonly used in moth sex pheromone glands to produce precursors for specific blends of acetates, alcohols, or aldehydes. Cascades of precursors are produced by combinations of unique A- -desaturases and limited chain-shortening steps. The six precursors for the cabbage looper blend (Figure 2) are in boldface type. 

In contrast to pheromones that involve single complex compounds, many moth species have been found to utilize a specific blend of relatively simple fatty acid-derived compounds. It appears that the evolution of a unique enzyme, A1 desaturase, used in combination with 2-carbon chain-shortening reactions (Figure 3) has allowed moth species to produce a variety of unsaturated acetates, aldehydes, and alcohols that can be combined in almost unlimited blends to impart species specificity. For example, biosynthetic precursors for the six-component pheromone blend of acetates for the cabbage looper moth (12) (Figure 2) can be determined easily from the cascade of acyl intermediates produced by the A11-desaturase and chain-shortening reactions (Figure 3). 

Aherne GW, Hardcastle A, Valenti M, Bryant A, Rogers P, Pettit GR, Srirangam JK, Kelland LR (1996) Antitumour evaluation of dolastatins 10 and 15 and their measurement in plasma by radioimmunoassay. Cancer Chemother Pharmacol 38 225-232 Ahmad S, Pardini S (1990) Antioxidant defense of the cabbage looper, Trichoplusia ni enzymatic responses to the superoxide-generating flavonoid, quercetin and photodynamic furanocou-marin, xantotoxin. Photochem Photobiol 51 305-312 Amsler CD, Fairhead VA (2006) Defensive and sensory chemical ecology of brown algae. Adv BotRes 43 1-91... 

Rutin and quercetin-3-glucosylgalactoside (flavonols) and genistein (isoflavone) Cabbage looper (Trichoplusia ni) Cited in 93... 

Many Insects have become specialists on crucifers and a few related plant families. These Include flea beetles, leaf beetles, cabbage root fly, aphids, cabbage butterflies and the dlamondback moth. At the same time, several polyphagous Insects such as the cabbage looper, armyworms and aphids are major pests of crucifers. Comparative studies on these specialists and generalists have provided valuable Information on host recognition and possible resistance mechanisms. 

This olefination protocol was applied to a short and efficient synthesis of (Z)-dodec-7-enyl acetate, the cabbage looper moth pheromone131. 

Landolt, P. J. (1993). Effects of host plant leaf damage on cabbage-looper moth attraction and oviposition. Entomologia Experimentalis etApplicata 67 79-85. 

Haynes, K.F., Zhao, J. Z. and Latif, A. (1991). Identification of floral compounds from Abelia grandiflora that stimulate upwind flight in cabbage looper moths. Journal of Chemical Ecology 17 637-646. 

Heath, R. R., Landolt, P. J., Dueben, B. and Senczewski, B. (1992). Identification of floral compounds of night-blooming jessamine attractive to cabbage looper moths. Environmental Entomology 21 854-859. 

Hydroxydanaidal has been extracted from coremata (Krasnoff and Roelofs, 1989). Like the cabbage looper moth, the salt marsh caterpillar moth has a dual signaling system, but in the case of E. acrea both males and females are attracted, leading to aggregations. 

Fig. 8.1. Pheromone biosynthetic pathway in the cabbage looper, Trichoplusia ni. Key steps are chain shortening (—2C) and A11 desaturation (All). Circled acyl-coenzyme A (CoA) derivatives are reduced and acetylated to form the pheromone components. (Modified from Jurenka et al., 1994.)...

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