I am trying to understand how the perfect imperative functioned in Latin. Is "Noli illud dixisse!" good Latin for "You should not have said that!"? I know "Noli illud dicere!" means "Do not say that!", and "dicere" means "to say", so it can be replaced with "dixisse" meaning "to have said", right?

Similarly, how would you say "You should have said it!" in Latin? Would it be "Illud dixto!"? I know "memento" is a perfect imperative originally meaning "You should have remembered!", but that, once the verb "meminisse" lost its present tense, it shifted its meaning to "Remember!".

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Woodcock in Paragraph 112 uses the imperfect subjunctive to express these meanings. Tu ne faceres tale, "you should not have behaved so", quoting Plautus. [Argentum] non redderes, "you shouldn't have returned the money", again Plautus. Following his lead, I'd go with Illud ne diceres or Illud non diceres to answer your question.

Later, in Paragraph 123, he gives examples using the past tenses of debeo. Again, following his lead, I would suggest Illud dicere non debuisti for "you shouldn't have said that".

Your suggestion of Noli illud dixisse is very interesting and thought provoking. It looks to me like good grammar, so it must mean something, but I'm not sure what. I think it probably would mean what you want it to mean, but I doubt that it is a natural idiom. Latin normally uses debeo for that sort of thing, and it conjugates debeo for tense while keeping the infinitive in the present.

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    Noli is a simple imperative instruction "Do not": Noli me tangere = Don't touch me (as the question says). Aug 29, 2021 at 8:25
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    @AndrewLeach: I think Figulus knows that, but he does not feel that using noli with a past infinitive would work (and I think I agree).
    – Cerberus
    Aug 30, 2021 at 0:46
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    @AndrewLeach Indeed. Noli illud dixisse means literally, "Do not want to have said that". It's perfectly good Latin grammar, just like my literal translation is perfectly good English grammar. But the English is rather clunky, and I suspect the Latin is clunky too. Dunno. But I do know that there are well attested ways of expressing the same thought, and I gave a couple of examples. I hope they help.
    – Figulus
    Aug 31, 2021 at 1:19

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