Nest defense is an adaptive strategy used by adults to increase survival of independent young. However, the risk adults face by defending young from predators represents an important trade-off and parental investment theory predicts adults will modulate nest defense based on the value of offspring. We used a model of a black rat snake, a potential nest predator on our study site, to quantify nest defense in a population of gray catbirds in eastern Pennsylvania during the breeding seasons of 2017 and 2018. Specifically, we evaluated (1) the difference in nest defense between male and female parents, (2) the relationship between nest defense and nest success, and (3) how variation in nest defense was related to factors associated with offspring value. Although male catbirds tend to be larger than females, they did not defend their nests more aggressively than female catbirds. Response to the model predator we used was also not different between individuals whose nests were successful compared with individuals that failed. Although nests that contained more and older young were not defended more aggressively, our analyses did show that adult catbirds defended young that were laid earlier in the season more intensely than those laid later in the breeding season. In birds, earlier clutch initiation is associated with an increased chance of recruitment into the breeding population. Catbirds, therefore, follow predictions of parental investment theory because they defended offspring of higher value more aggressively. Significance statement Defense of young from predators is an important component of parental care. Nest defense represents a trade-off because although it should increase reproductive success by increasing offspring survival, it presents a risk to adults, thus lowering their survival. We studied variation in nest defense of gray catbirds in relation to offspring value. Although nest defense was not related to nest success, we did find that adult catbirds defended nests that were produced earlier in the year more aggressively than later nests. In birds, the timing of reproduction is linked to prospects of juvenile survival in such a way that offspring produced early in the breeding season are more likely to survive and recruit into the breeding population. As predicted by parental investment theory, catbirds defended young that represented a higher increase in fitness more aggressively.

A series of fourteen 2-aryl-3-phenyl-2,3-dihydro-4H-pyrido[3,2-e][1,3]thiazin-4-ones was prepared at room temperature by T3P-mediated cyclization of N-phenyl-C-aryl imines with thionicotinic acid, two difficult substrates. The reactions were operationally simple, did not require specialized equipment or anhydrous solvents, could be performed as either two or three component reactions, and gave moderate–good yields as high as 63%. This provides ready access to N-phenyl compounds in this family, which have been generally difficult to prepare. As part of the study, the first crystal structure of neutral thionicotinic acid is also reported, and showed the molecule to be in the form of the thione tautomer. Additionally, the synthesized compounds were tested against T. brucei, the causative agent of Human African Sleeping Sickness. Screening at 50 µM concentration showed that five of the compounds strongly inhibited growth and killed parasites.