Never.

Lenses, like other tools, should be judged by one thing only: Do they do what you need them to do?

Whether a lens is "out of date" or not depends totally on the use to which you plan to put the lens. The decision should be based on the optical performance and other design factors of the lens and how well it meets the suitability for your needs, not when that lens was first released. If you can't articulate what your needs in a wide angle lens are, then there's no way to answer the question of which is the better lens, or even which is the better value for you.

There are some Canon lenses from the early to mid 1990s that are still in their active catalog and perform at the same level as many of their newer designs. The EF 135mm f/2 L is such a lens. There are others that are more than a bit outdated, particularly the first EF-S 'kit' lenses in the mid-2000s which suffered from quality control issues.

Optics has been around a lot longer than digital photography, and it is a more mature discipline. Particularly with regard to prime lenses, lens design is very mature. There have been advances in the past few years, but most have been in the areas of lens coatings (which affect some types of photos much more than others) and manufacturing techniques that allow easier/cheaper construction of high quality optical designs that have been around for a long time.

There have also been advances in non-optical aspects of lenses: focus motor technology (both in terms of video and stills), weather sealing, materials science that affects durability and resistance to environmental extremes beyond dust and moisture, etc.

If you shoot a lot in situations where the sun is backlighting your subjects, the improved anti-flare coatings of an EF 35mm f/1.4 L II vs. the older EF 35mm f/1.4 L can be crucial. If you shoot under controlled conditions in the studio, the differences are near meaningless. If you shoot in all kinds of weather better build quality and weather resistance will be significant. If you're a sunny day only shooter, it won't.

How much of all of these things affects your comparison of two specific lenses will be determined by whether these things would make a difference to what you shoot and the environments in which you shoot.

In terms of the two lenses you are comparing, the biggest difference is the type of focus motor. If you shoot a lot of video using AF, the STM motor will allow smoother and quieter focus changes. If you're shooting stills, the older USM lens is designed to focus quickly with a dedicated PDAF system rather than smoothly and quietly with sensor based CDAF (or sensor Dual Pixel CMOS AF for models that have it).

Another difference, as you have noted, is that the older EF-S 10-22mm f/3.5-4.5 is about 2/3 stop faster at most common focal lengths than the EF-S 10-18mm f/4.5-5.6 IS STM. If you're shooting landscapes in bright light you're probably stopping down both lenses anyway, so this wouldn't be much of a factor. But if you're shooting a lot of early morning and late afternoon environmental portraits with dimmer light, it could make a significant difference if you're holding the camera in your hands or there is movement in the scene (a human or animal subject, wind driven clouds or trees, etc.). Neither lens is fast enough to be considered a "low light" lens. The newer STM does have Image Stabilization, which helps with camera movement when shooting handheld but does nothing for subject motion. Based on a few reviews, the IS seems to be optimized for smooth video shooting. On the other hand, if you're shooting from a tripod then IS isn't a consideration and the faster aperture of the other lens helps with motion in the scene by allowing a faster shutter time.

In the case of these two lenses with very similar performance, the price difference may be the determining factor. The newer EF-S 10-18mm f/4.5-5.6 IS STM sells for less than half the older EF-s 10-24mm f/3.5-4.5.