Tested the issue in Android and able to reproduce the issue. 

Steps Followed:
1. Enabled talkback
2. Opened chorme and clicked on 3 dot menu
3. Selected Desktop site and clicked on it to enable, Talkback doesn't read state of checkbox

Chrome versions tested:
60.0.3072.0, 68.0.3440.91, 70.0.3523.0
OS:
Android 7.0.0

Android Devices:
Samsung galaxy J7

This issue is seen from M-60. Hence considering this issue as Non-Regression and marking as Untriaged.

Thanks!

I believe tedchoc@ did some work here recently. 

@#2, For accessibility, we're not actually aiming to have it read the checkbox.  We are hoping for it to read different strings based on the checkbox state:
Turn off Request desktop site
  vs
Turn on Request desktop site

Are you hearing different text or are you always hearing "Desktop site".  I hear just Desktop site, but I'm testing on P.

I don't recall doing anything with RDS, but maybe I'm forgetting something.

dfalcantara@ was the last one to make a large change:
https://codereview.chromium.org/2951133003

huayinz@ changed it from Request Desktop Site -> Desktop Site
https://chromium-review.googlesource.com/699745

I wonder if this is Android version specific.

I lied I did change this: https://chromium-review.googlesource.com/606677, but after looking at this, I'm not convinced this ever worked as we expected (or hasn't in a very long time).

The following revision refers to this bug:
  https://chromium.googlesource.com/chromium/src.git/+/fe3aba34c65af233e2877da15b4d8d7bc90ff402

commit fe3aba34c65af233e2877da15b4d8d7bc90ff402
Author: Ted Choc <tedchoc@google.com>
Date: Sat Aug 18 00:30:36 2018

Fix the accessibility string for the RDS menu option.

BUG= 874457 

Change-Id: I51adca20f4f73ec2e41fab2d9c9f3b736d473b99
Reviewed-on: https://chromium-review.googlesource.com/1179125
Reviewed-by: Becky Zhou <huayinz@chromium.org>
Commit-Queue: Ted Choc <tedchoc@chromium.org>
Cr-Commit-Position: refs/heads/master@{#584259}
[modify] https://crrev.com/fe3aba34c65af233e2877da15b4d8d7bc90ff402/chrome/android/java/src/org/chromium/chrome/browser/appmenu/AppMenuAdapter.java
[modify] https://crrev.com/fe3aba34c65af233e2877da15b4d8d7bc90ff402/chrome/android/java/src/org/chromium/chrome/browser/appmenu/AppMenuPropertiesDelegate.java