Co-crystals
The present invention relates to co-crystals of cyprodinil or pyrimethanil and a co-crystal forming compound which has at least one organic acid functional group. In particular, the present invention relates to co-crystals of cyprodinil and benzoic acid, succinic acid, fumaric acid, maleic acid, oxalic acid, pyrazine carboxylic acid, glycolic acid, levulinic acid, (2-methylphenoxy)acetic acid, hexanedioic acid, 4-(methylamino) benzoic acid, trimethyl acetic acid, pyruvic acid or 4-hydroxy-4′-biphenyl carboxylic acid.
1. A co-crystal comprising cyprodinil and a co-crystal forming compound which has at least one organic acid functional group, wherein said co-crystal forming compound is:
a) benzoic acid and the co-crystal is characterised by a powder X-ray diffraction pattern expressed in terms of 2 theta angles, wherein the powder X-ray diffraction pattern comprises the 2 theta angle values 11.201, 11.660, 13.978, 15.050, 18.584,19.297, 20.793, 23.865, 25.697, and 26.765; or
b) succinic acid and the co-crystal is characterised by a powder X-ray diffraction pattern expressed in terms of 2 theta angles, wherein the powder X-ray diffraction pattern comprises the 2 theta angle values 12.5, 17.3, 18.7, 21.0, 22.4, 24.0, 25.4, 28.8 and 29.3; and
wherein hydrogen-bonding occurs between the co-crystal forming compound and the cyprodinil.
2. The co-crystal of claim 1 , wherein the co-crystal forming compound is succinic acid.
3. A process of preparing a co-crystal of claim 1 comprising
a) grinding, heating or contacting in solution cyprodinil with the co-crystal forming compound, under crystallisation conditions so as to form a solid phase;
b) isolating co-crystals comprising cyprodinil and the co-crystal forming compound.
4. A fungicidal composition comprising the co-crystal of claim 1 .
5. The composition of claim 4 which is an agrochemical composition.
6. A method of preventing/controlling fungal infection on plants comprising treating the plant with a fungicidally effective amount of an agricultural composition of claim 5 .