Thermodynamically stable crystal modification of 2-({2-chloro-4-(methylsulfonyl)-3-[(2,2,2-trifluoroethoxy)methyl]phenyl} carbonyl)cyclohexane-1,3-dione
View Patent ↗What is described is a thermodynamically stable crystal modification of the herbidically active compound 2-({2-chloro-4-(methylsulfonyl)-3-[(2,2,2-trifluoroethoxy)methyl]phenyl}carbonyl)cyclohexan-1,3-dione (tembotrione). This thermodynamically stable crystal modification has particular advantages in the stability of suspension formulations.
1. A crystal modification of 2-({2-chloro-4-(methylsulfonyl)-3-[(2,2,2-trifluoro-ethoxy)methyl]phenyl}carbonyl)cyclohexan-1,3-dione (tembotrione) in an orthorhombic system, where the crystal modification has
(a) an infrared spectrum having the following band maxima stated in cm −1 :
593
883
1196
1553
612
921
1253
1675
654
951
1282
2897
686
966
1298
2926
765
994
1336
2959
777
1010
1356
3010
786
1085
1386
3075
813
1112
1409
836
1138
1417
853
1164
1461
and/or
(b) a Raman spectrum having the following band maxima stated in cm −1 :
91
507
921
1337
130
517
952
1358
171
540
968
1377
192
550
1002
1418
213
599
1053
1461
265
613
1075
1557
279
655
1116
1587
291
675
1141
1665
311
687
1166
1679
363
738
1176
2888
402
775
1197
2925
431
813
1272
2971
445
836
1289
2978
460
853
1300
3010
490
883
1325
3075
and/or
(c) an X-ray powder diffractometry pattern having the following peaks stated in degrees 2θ:
7.3765
20.8117
26.6207
32.4069
8.0674
21.1093
27.2879
32.8121
10.7988
21.5838
27.4979
33.1960
13.5030
21.6983
27.9884
33.5965
14.7553
23.5072
28.2728
34.4007
16.4462
23.9969
28.5989
35.1147
16.6192
24.3808
29.0017
35.7136
17.0512
24.8173
30.0318
35.9960
17.1467
25.0316
30.2456
36.4372
17.6444
25.2513
30.6058
36.7974.
17.7792
25.5214
30.7628
19.3008
25.7119
31.2971
20.4034
25.9248
31.6675
2. The crystal modification as claimed in claim 1 , where the orthorhombic system has the space group Pna2 1 .
3. The crystal modification as claimed in claim 1 , wherein the unit cell has the following dimensions:
a = 31.1647(18) Å
= 90°
b = 10.3522(6) Å
= 90°
c = 5.5449(3) Å
= 90°.
4. The crystal modification as claimed in claim 1 having a melting point of 124.0° C.
5. A herbicidal composition characterized by a content of thermodynamically stable crystal modification of tembotrione as claimed in claim 1 and at least one extender and/or surface-active auxiliary.
6. A herbicidal composition comprising the thermodynamically stable crystal modification of tembotrione as claimed in claim 1 and a metastable crystal modification or a mixture of the metastable crystal modification of tembotrione, wherein the composition comprises at least 80% by weight of the stable crystal modification.
7. A composition for controlling unwanted plants comprising the thermodynamically stable crystal modification of tembotrione as claimed in claim 1 .
8. A method for controlling unwanted plants, comprising allowing the thermodynamically stable crystal modification of tembotrione as claimed in claim 1 to act on the unwanted plants and/or a habitat thereof.
9. The method as claimed in claim 8 for controlling harmful plants in crops of monocotyledonous plants.
10. The method as claimed in claim 8 , where the crop plants are genetically modified and/or have been obtained by mutation selection.
11. The method of claim 9 , where the crop plants are genetically modified and/or have been obtained by mutation selection.