3-Propyl-l,2-dithiolane

A predator odor affected a pocket gopher, Thomomys talpoides, population in western Canada. First live-trapping removed the gophers from plots of 4ha area in an orchard. Then synthetic sulfur compounds from stoat, Mustek erminea anal glands (1 1 mixture of 2-propylthietane and 3-propyl-l,2-dithiolane) were... 

Propyl-l,2-dithiolane Stoat AGS Montane vole Sullivan eta/., 1988... 

Animal Sources. The marine annelid worm Lumbrineris hetero-poda produces an insect toxin nereistoxin, 24, 4-N,N-dimethyl-amino-1,2-dithiolane (5 ). The mink MusteXa vison) affords 2,2-dimethylthietane, 14, and 3,3-dimethy1-1,2-dithiolane, 25 (28,63, 64), the ferret Musteta putoris) secretes 14, 25, cis- and trans-2,3-dimethylthietane, 2-propyl- and 2-pentyl-thietane, cis and trans-3,4-dimethyl-l,2-dithiolane, and 3-propyl-l,2-dithiolane (65), and the stoat (Mustela erminea) contains 2-ethyl-, 2-propyl-, and 2-pentyl-thietane, and 3-ethyl- and 3-propyl-l,2-dithiolane in its anal gland (5, ). These several thiaheterocycles from mustela species probably function as scent markers. 

A generous gift of 3-propyl-l,2-dithiolane and of ipsenol was received from D. Wackerchuck (Phero Tech, Inc.). J.H. Borden and L. Chong (Simon Fraser University) contributed a sample of sulcatol. 

N spectrum of formamide (decou- 7.1 3-Propyl-l, 2-dithiolane 3 (6 spectra)... 

With the proton connectivities and chemical shifts in hand, the HETCOR spectrum establishes the —13C correlations. This is left as an exercise. It remains only to insert the two sulfur atoms in the above diagram to give 3-propyl-l,2-dithiolane. 

The responses of gophers to the weasel mixture and single anal gland compounds are illustrated in Figure 3. There was no difference in responses between males and females in these trials. Gophers clearly avoided the 2-propylthietane, polymerized 3-propyl-l,2-dithiolane, and the weasel mixture. They also tended to avoid the 3,3-dimethyl-l,2-dithiolane from the ferret with the following results from 3 trials (control vs. treatment) 14-9 14-9 8-1. The control test, fresh 3-propyl-l,2-dithiolane, and 2-methylthiophene (novel odor) had little effect on gopher behavior. 

Fig. 4. Responses of pocket gophers to mustelid anal gland compounds in the field at Vernon study area. 3PDIT = 3-propyl-l,2-dithiolane. DMDI 3,3-dimethyl-l,2-dithiolane. p < 0.05 significant difference by chi-square. 

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