These characters all mean "to attack" or "to invade", but what are the differences between them? When should one be used and not the others?
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it is hard to tell what they exactly mean without contexts, but i can give you a very general idea of these characters:
征 (zheng1) means 'wage war by travelling a long distance'. it is usually associated with a war with a very large scale in both space and time.
伐 (fa2) is just 'to wage war against', nothing more. in fact, among all five characters, only the original meaning of 伐 is directly related with war.
讨 (tao3), literally "to demand", means "to wage war demanding justice/punish the wrongdoers"
侵 (qin1) means “to invade" or "to encroach"
袭 (xi2) is usually associated with “sudden attack”.
As single characters they are only used in classical Chinese scripts, and their level of just decreases as has been listed before.
征 usually describes a war initiated by the emporor against local rebels/nomades.
伐 describes a war between emporors/kings/dukes because of various affairs political, marital, etc.
讨 describes a war initiated by a low class, sometimes a minister, against a high class. e.g.讨武曌檄文
侵 describes a war unfair without proper Casus Belli, typically strong kingdoms bullying weak kungdoms.
袭 describes a battle initiated when the opponent is unprepared.
攻 means to attack on a general sense.
Note: Meaning of characters can only help you to understand words, but since mandarin has gone through so many years, it does not have a rigid way of composing words from characters. And in classical Chinese, characters may have plural meanings, and character used for the same meaning changes with time.
although I'm a native speaker, I still can't tell you the difference between them. In fact they have the same meaning, maybe include some little difference.
we always use them as following method: 征伐, 征讨, 侵袭
but don't mind it. Chinese is not a strict language. for example, elevator and escalator,we just use one word to describe them:电梯 sometimes we also use 手扶梯 to specific the escalator. But nobody will be puzzle when you say elevator when you point to a escalator.