Abstract
The present invention relates to compounds of the formula (I), in particular to phenylamidines of the formula (I), to a process for their preparation, to the use of phenylamidines of the formula (I) according to the invention for controlling unwanted microorganisms, in particular phytopathogenic fungi and also to a composition for this purpose, comprising the phenylamidines of the formula (I) according to the invention. Furthermore, the invention relates to a method for controlling unwanted microorganisms, in particular phytopathogenic fungi, characterized in that the compounds of the formula (I) are applied to the microorganisms, in particular to the phytopathogenic fungi and/or in their habitat.
##STR00001##
Claims
1. A compound of formula (I) ##STR00020## wherein: R.sup.1 is selected from the group consisting of C.sub.1-C.sub.8-alkyl and C.sub.3-C.sub.7-cycloalkyl which may be independently non-substituted or substituted by one or more group(s) selected from the group consisting of halogen and C.sub.1-C.sub.8-alkoxy; R.sup.2 and R.sup.3 are each independently selected from the group consisting of halogen, cyano, C.sub.1-C.sub.8-alkyl, C.sub.3-C.sub.7-cycloalkyl, OC.sub.1-C.sub.8-alkyl, C.sub.2-C.sub.8-alkenyl, C.sub.2-C.sub.8-alkynyl, Si(R.sup.3a)(R.sup.3b)(R.sup.3c), C(O)C.sub.1-C.sub.8-alkyl, C(O)C.sub.3-C.sub.7-cycloalkyl, C(O)NHC.sub.1-C.sub.8-alkyl, C(O)N-di-C.sub.1-C.sub.8-alkyl, C(O)OC.sub.1-C.sub.8-alkyl, S(O).sub.nC.sub.1-C.sub.8-alkyl, NHC.sub.1-C.sub.8-alkyl, and N-di-C.sub.1-C.sub.8-alkyl, which may be independently non-substituted or substituted by one or more group(s) selected from the group consisting of halogen and C.sub.1-C.sub.8-alkoxy; wherein R.sup.3a, R.sup.3b, and R.sup.3c are independently from each other phenyl or C.sub.1-C.sub.8-alkyl; and n is 0, 1 or 2; R.sup.4, R.sup.5, R.sup.6, R.sup.7 and R.sup.8 are each independently selected from the group consisting of H, halogen, cyano, C.sub.1-C.sub.8-alkyl, C.sub.3-C.sub.7-cycloalkyl, OC.sub.1-C.sub.8-alkyl, C.sub.2-C.sub.8-alkenyl, C.sub.2-C.sub.8-alkynyl, Si(R.sup.3a)(R.sup.3b)(R.sup.3c), C(O)C.sub.1-C.sub.8-alkyl, C(O)C.sub.3-C.sub.7-cycloalkyl, C(O)NHC.sub.1-C.sub.8-alkyl, C(O)N-di-C.sub.1-C.sub.8-alkyl, C(O)OC.sub.1-C.sub.8-alkyl, S(O).sub.nC.sub.1-C.sub.8-alkyl, NHC.sub.1-C.sub.8-alkyl, N-di-C.sub.1-C.sub.8-alkyl, and C.sub.6-C.sub.14-aryl, which may be independently non-substituted or substituted by one or more group(s) selected from the group consisting of halogen, methyl, halomethyl, and C.sub.1-C.sub.8-alkoxy; wherein R.sup.3a, R.sup.3b, and R.sup.3c are independently from each other phenyl or C.sub.1-C.sub.8-alkyl; and n is 0, 1 or 2; or in which R.sup.4 and R.sup.5 can form, together with the atom to which they are bonded or with additional atoms chosen from N, O, P and S, a 3- to 7-membered ring selected from the group consisting of cycloalkyl and heterocyclyl, which may optionally be substituted by one or more halogen group(s), and wherein R.sup.6, R.sup.7 and R.sup.8 are as defined above; or in which R.sup.4 and R.sup.5 together can form a double bonded substituent CR.sup.9R.sup.10, wherein R.sup.9 and R.sup.10 are each independently selected from the group consisting of H, halogen, Me and Et, and wherein R.sup.6, R.sup.7 and R.sup.8 are as defined above; or a salt, an N-oxide, or a metal complex thereof, or a stereoisomer of any of the foregoing.
2. The compound according to claim 1, wherein R.sup.1 is C.sub.1-C.sub.8-alkyl, R.sup.2 is selected from the group consisting of halogen, cyano, and C.sub.1-C.sub.8-alkyl which may be independently non-substituted or substituted by one or more group(s) selected from the group consisting of halogen and C.sub.1-C.sub.8-alkoxy; R.sup.3 is selected from the group consisting of halogen, cyano, and C.sub.1-C.sub.8-alkyl which may be independently non-substituted or substituted by one or more group(s) selected from the group consisting of halogen and C.sub.1-C.sub.8-alkoxy; R.sup.4 and R.sup.5 are selected from the group consisting of H, halogen, cyano, and C.sub.1-C.sub.8-alkyl which may be independently non-substituted or substituted by one or more group(s) selected from the group consisting of halogen and C.sub.1-C.sub.8-alkoxy; or R.sup.4 and R.sup.5 can form, together with the atom to which they are bonded or with additional atoms chosen from N, O, P and S, a 3- to 7-membered ring selected from the group consisting of cycloalkyl and heterocyclyl, which may optionally be substituted by one or more halogen group(s); or in which R.sup.4 and R.sup.5 together can form a double bonded substituent CR.sup.9R.sup.10, wherein R.sup.9 and R.sup.10 are each independently selected from the group consisting of H, F, Cl, Me and Et; R.sup.6, R.sup.7 and R.sup.8 are independently selected from the group consisting of H, F, Cl, cyano, Me, methoxy, phenyl and phenyl substituted by one or more substituents selected from the group consisting of halogen, Me and CF.sub.3; or a salt, an N-oxide, or a metal complex thereof, or a stereoisomer of any of the foregoing.
3. The compound according to claim 1, wherein R.sup.1 is selected from the group consisting of Me, Et, and iPr; R.sup.2 is selected from the group consisting of Me, cyano, Cl, Br, I, CHF.sub.2, and CF.sub.3; R.sup.3 is selected from the group consisting of Me, Cyano, F, Cl, Br, and I; R.sup.4 and R.sup.5 are each H; or R.sup.4 and R.sup.5 can form, together with the atom to which they are bonded or with additional atoms chosen from N, O, P and S, a 3- to 7-membered ring selected from the group consisting of cycloalkyl and heterocyclyl, which may optionally be substituted by one or more halogen group(s); or in which R.sup.4 and R.sup.5 together can form a double bonded substituent CH.sub.2; R.sup.6 is selected from the group consisting of H, Me, cyano, and F; R.sup.7 and R.sup.8 are each H; or a salt, an N-oxide, or a metal complex thereof, or a stereoisomer of any of the foregoing.
4. The compound according to claim 1, wherein R.sup.l is C.sub.1-C.sub.8-alkyl, R.sup.2 is selected from the group consisting of halogen, cyano, and C.sub.1-C.sub.8-alkyl which may be independently non-substituted or substituted by one or more halogen group(s); R.sup.3 is selected from the group consisting of halogen, cyano, and C.sub.1-C.sub.8-alkyl which may be independently non-substituted or substituted by one or more halogen group(s); R.sup.4 and R.sup.5 are selected from the group consisting of H, halogen, cyano, and C.sub.1-C.sub.8-alkyl which may be independently non-substituted or substituted by one or more halogen group(s); or R.sup.4 and R.sup.5 can form, together with the atom to which they are bonded a 3- to 6-membered cycloalkyl ring, which may optionally be substituted by one or more halogen group(s); or in which R.sup.4 and R.sup.5 together can form a double bonded substituent CR.sup.9R.sup.10, wherein R.sup.9 and R.sup.10 are each independently selected from the group consisting of hydrogen, Me and Et; R.sup.6, R.sup.7 and R.sup.8 are independently selected from the group consisting of H, F, Cl, cyano, Me, methoxy and phenyl; or a salt, an N-oxide, or a metal complex thereof, or a stereoisomer of any of the foregoing.
5. The compound according to claim 1, wherein R.sup.1 is selected from the group consisting of Me, Et, and iPr; R.sup.2 is selected from the group consisting of Me, cyano, Cl, Br, I, CHF.sub.2, and CF.sub.3; R.sup.3 is selected from the group consisting of Me, iPr, Cyano, F, Cl, Br, and I; R.sup.4 and R.sup.5 are each independently selected from the group consisting of H and Me; or R.sup.4 and R.sup.5 can form, together with the atom to which they are bonded a cyclopropyl, which may optionally be substituted by one or more group(s) selected from the group consisting of F, Cl and Br; or in which R.sup.4 and R.sup.5 together can form a double bonded substituent CH.sub.2; R.sup.6 is selected from the group consisting of H, Me, cyano, F, Cl, methoxy and phenyl; R.sup.7 is selected from the group consisting of H and F, and R.sup.8 is selected from the group consisting of H and F; or a salt, an N-oxide, or a metal complex thereof, or a stereoisomer of any of the foregoing.
6. The compound according to claim 1, wherein R.sup.1 is selected from the group consisting of Et and iPr; R.sup.2 is selected from the group consisting of Me and Cl; R.sup.3 is selected from the group consisting of Me, F and Cl; R.sup.4 is selected from the group consisting of H and Me, and R.sup.5 is H; or R.sup.4 and R.sup.5 can form, together with the atom to which they are bonded a cyclopropyl, which may optionally be substituted by one or two F; or in which R.sup.4 and R.sup.5 together can form a double bonded substituent CH.sub.2; R.sup.6 is selected from the group consisting of H, Me, cyano, F and Cl; R.sup.7 is selected from the group consisting of H and F, and R.sup.8 is selected from the group consisting of H and F; or a salt, an N-oxide, or a metal complex thereof, or a stereoisomer of any of the foregoing.
7. A process for preparing a compound as claimed in claim 1 which comprises at least one of the following steps (a) to (g): (a) reacting an aniline derivative of formula (II) to afford a derivative of formula (III) according to the reaction scheme below: ##STR00021## (b) reacting a derivative of formula (III) with a benzyl derivative of formula (IV) to afford a derivative of formula (V) in accordance with the reaction scheme below: ##STR00022## (c) coupling a nitrobenzene derivative of formula (VI) with a boronic acid or an ester of formula (VII) to afford an alkenyl derivative of formula (VIII) according to the reaction scheme below: ##STR00023## (d) reacting an alkenyl derivative of formula (VIII) to afford a cyclopropyl derivative of formula (IX) according to the reaction scheme below: ##STR00024## (e) reducing a nitrobenzene derivative of formula (IX) to an aniline derivative of formula (V) according to the reaction scheme below: ##STR00025## (f) reacting an aniline of formula (V) with an aminoacetal to afford an amidine of formula (I) according to the scheme below: ##STR00026## (g) reacting an organometallic compound of formula (X) with an aniline derivative of formula (II) to afford an aniline of formula (V) according to the scheme below: ##STR00027## where in the above schemes: Z is selected from the group consisting of Cl, Br, I and OSO.sub.2CF.sub.3; M is selected from the group consisting of MgZ and ZnZ; R.sup.1 to R.sup.8 have the meanings as in claim 1.
8. A composition comprising the compound as claimed in claim 1, or a salt, an N-oxide, or a metal complex thereof, or a stereoisomer of any of the foregoing, and further comprising an auxiliary, a solvent, a carrier, a surfactant, or an extender.
9. (canceled)
10. A method for controlling phytopathogenic fungi in crop protection, comprising applying the compound as claimed in claim 1, or a salt, an N-oxide, or a metal complex thereof, or a stereoisomer of any of the foregoing, to the phytopathogenic fungi and/or their habitat.
11. A seed comprising the compound as claimed in claim 1, or a salt, an N-oxide, or a metal complex thereof, or a stereoisomer of any of the foregoing.
12. A method for treating a seed comprising applying the compound as claimed in claim 1, or a salt, an N-oxide, or a metal complex thereof, or a stereoisomer of any of the foregoing, to the seed.
13. A method for treating a transgenic plant comprising applying the compound as claimed in claim 1, or a salt, an N-oxide, or a metal complex thereof, or a stereoisomer of any of the foregoing, to the transgenic plant.
14. A method for treating a seed of a transgenic plant comprising applying the compound as claimed in claim 1, or a salt, an N-oxide, or a metal complex thereof, or a stereoisomer of any of the foregoing, to the seed of the transgenic plant.
15. A method for protecting a seed against phytopathogenic fungi comprising treating the seed with at least one compound as claimed in claim 1, or a salt, an N-oxide, or a metal complex thereof, or a stereoisomer of any of the foregoing.
16. A method for controlling phytopathogenic fungi in crop protection, comprising applying the composition according to claim 8 to the phytopathogenic fungi and/or their habitat.
17. A seed comprising the composition according to claim 8.
18. A method for treating a seed comprising applying the composition according to claim 8 to the seed.
19. A method for treating a transgenic plant comprising applying the composition according to claim 8 to the transgenic plant.
20. A method for treating a seed of a transgenic plant comprising applying the composition according to claim 8 to the seed of the transgenic plant.
21. A method for protecting seed against phytopathogenic comprising treating the seed with the composition according to claim 8.
Description
EXAMPLES
[0305]
TABLE-US-00002 (I) [00019]![embedded image]()
Ex No LogP NMR PeakList IUPAC name 1 1.41[a]; Example 1: 1H-NMR(400.0 MHz, d6-DMSO): N-[2-chloro-4-[(2- 3.86[b] = 7.852 (2.1); 7.833 (2.2); 7.730 (1.1); 7.662 (1.0); cyanophenyl)methyl]-5- 7.659 (1.0); 7.642 (2.2); 7.639 (2.2); 7.623 (1.6); methylphenyl]-N-ethyl-N- 7.620 (1.6); 7.456 (1.4); 7.437 (2.3); 7.419 (1.0); methylmethanimidamide 7.211 (2.2); 7.192 (2.0); 6.944 (5.9); 6.842 (1.5); 5.756 (1.2); 4.079 (8.4); 3.422 (0.5); 3.347 (1.1); 3.320 (11.9); 2.986 (1.4); 2.918 (3.7); 2.671 (0.3); 2.506 (46.0); 2.502 (60.8); 2.497 (44.2); 2.328 (0.3); 2.146 (16.0); 1.398 (0.4); 1.149 (1.9); 1.132 (3.8); 1.115 (2.1); 0.008 (0.6); 0.000 (17.3) 2 1.52[a]; Example 2: 1H-NMR(400.0 MHz, d6-DMSO): N-[2-chloro-4-[(2- 4.50[b] = 7.706 (1.2); 7.592 (0.4); 7.306 (0.4); 7.300 (0.4); fluorophenyl)methyl]-5- 7.286 (1.0); 7.268 (1.4); 7.253 (0.7); 7.249 (0.7); methylphenyl]-N-ethyl-N- 7.200 (1.5); 7.177 (1.7); 7.154 (1.0); 7.148 (1.1); methylmethanimidamide 7.129 (2.4); 7.109 (1.9); 7.100 (1.4); 7.085 (1.6); 7.082 (1.5); 7.066 (0.6); 6.977 (5.3); 6.804 (1.6); 3.873 (7.7); 3.428 (0.5); 3.414 (0.5); 3.321 (52.1); 2.977 (1.4); 2.912 (3.7); 2.670 (0.4); 2.506 (55.8); 2.501 (72.3); 2.497 (55.0); 2.328 (0.4); 2.152 (16.0); 2.067 (0.4); 1.144 (2.2); 1.127 (4.4); 1.110 (2.4); 0.000 (64.6) 3 1.49[a] Example 3: 1H-NMR(400.0 MHz, d6-DMSO): N-(4-benzyl-2-chloro-5- = 7.696 (1.0); 7.583 (0.4); 7.301 (1.7); 7.283 (4.5); methylphenyl)-N-ethyl-N- 7.264 (3.3); 7.197 (1.4); 7.179 (2.2); 7.160 (0.8); methylmethanimidamide 7.137 (4.1); 7.118 (3.4); 7.062 (5.7); 6.778 (1.5); 3.865 (8.2); 3.414 (0.5); 3.321 (52.3); 2.973 (1.2); 2.911 (3.2); 2.670 (0.4); 2.505 (45.1); 2.501 (61.4); 2.497 (47.2); 2.328 (0.4); 2.123 (16.0); 2.040 (0.4); 1.142 (2.5); 1.125 (5.1); 1.107 (2.5); 0.008 (2.2); 0.000 (58.0); 0.008 (3.1) 4 1.38[a]; Example 4: 1H-NMR(400.0 MHz, d6-DMSO): N-[5-chloro-4-[(2- 4.38[b] = 7.837 (2.7); 7.819 (2.9); 7.752 (1.2); 7.638 (1.6); cyanophenyl)methyl]-2- 7.618 (2.8); 7.599 (1.7); 7.438 (1.8); 7.419 (3.0); methylphenyl]-N-ethyl-N- 7.400 (1.4); 7.186 (3.0); 7.166 (2.8); 6.999 (6.1); methylmethanimidamide 6.914 (1.6); 5.757 (1.3); 4.157 (11.3); 3.424 (0.6); 3.349 (1.3); 3.324 (36.5); 2.984 (1.5); 2.916 (3.8); 2.507 (38.9); 2.502 (50.6); 2.498 (36.5); 2.120 (16.0); 1.142 (2.6); 1.125 (5.1); 1.108 (2.7); 0.000 (8.5) 5 1.58[a]; Example 5: 1H-NMR(400.0 MHz, d6-DMSO): N-[5-chloro-4-+(2- 2.99[b] = 7.729 (1.0); 7.622 (0.4); 7.290 (0.4); 7.283 (0.6); fluorophenyl)methyl]-2- 7.276 (0.8); 7.270 (1.1); 7.255 (1.6); 7.248 (1.0); methylphenyl]-N-ethyl-N- 7.239 (0.8); 7.234 (0.8); 7.185 (1.9); 7.162 (2.0); methylmethanimidamide 7.159 (2.0); 7.139 (1.3); 7.131 (0.9); 7.111 (2.9); 7.104 (2.0); 7.096 (3.9); 7.085 (1.8); 7.081 (1.7); 7.067 (0.6); 6.966 (5.5); 6.879 (1.6); 3.955 (9.7); 3.416 (0.6); 3.331 (84.7); 2.976 (1.3); 2.910 (3.4); 2.671 (0.4); 2.667 (0.3); 2.506 (55.7); 2.502 (74.2); 2.498 (55.8); 2.329 (0.4); 2.103 (16.0); 1.232 (1.4); 1.138 (2.6); 1.121 (4.9); 1.104 (2.7); 0.008 (2.7); 0.000 (71.3); 0.008 (3.3) 6 1.72[a]; Example 6: 1H-NMR(601.6 MHz, d6-DMSO): N-(4-benzyl-5-chloro-2- 5.16[b] = 19.971 (0.3); 7.712 (0.7); 7.603 (0.3); 7.280 (3.3); methylphenyl)-N-ethyl-N- 7.268 (6.0); 7.260 (1.1); 7.255 (5.7); 7.179 (9.0); methylmethanimidamide 7.168 (7.3); 7.156 (1.3); 7.040 (6.6); 6.850 (1.1); 3.941 (12.8); 3.419 (0.5); 3.332 (0.9); 3.304 (70.5); 2.972 (0.9); 2.906 (2.3); 2.612 (0.6); 2.521 (1.1); 2.518 (1.4); 2.515 (1.3); 2.506 (33.9); 2.503 (77.0); 2.500 (108.8); 2.497 (78.1); 2.494 (35.4); 2.384 (0.6); 2.178 (0.5); 2.110 (16.0); 1.130 (2.1); 1.119 (4.1); 1.108 (2.4); 0.005 (0.4); 0.000 (17.8); 0.006 (0.5) 7 1.92[a]; Example 7: 1H-NMR(400.0 MHz, d6-DMSO): N-[4-[(2- 5.16[b] = 7.605 (0.5); 7.586 (0.4); 7.470 (0.4); 7.460 (2.1); chlorophenyl)methyl]-2,5- 7.452 (2.1); 7.447 (1.7); 7.437 (2.6); 7.428 (0.4); dimethylphenyl]-N-ethyl- 7.256 (0.7); 7.246 (5.2); 7.237 (4.0); 7.231 (3.8); N-methylmethanimidamide 7.223 (5.1); 7.213 (0.6); 6.958 (1.9); 6.948 (1.6); 6.944 (1.8); 6.935 (1.6); 6.699 (5.3); 6.602 (3.7); 3.907 (9.8); 3.317 (43.1); 2.918 (3.6); 2.675 (0.4); 2.670 (0.6); 2.666 (0.4); 2.523 (1.8); 2.510 (33.9); 2.506 (68.4); 2.501 (93.2); 2.497 (70.1); 2.492 (34.6); 2.332 (0.4); 2.328 (0.5); 2.324 (0.4); 2.087 (16.0); 2.072 (15.7); 1.998 (0.3); 1.988 (0.9); 1.398 (2.9); 1.175 (0.5); 1.136 (4.9); 1.118 (10.5); 1.100 (4.8); 0.008 (1.2); 0.000 (30.4); 0.008 (1.2) 8 1.47[a]; Example 8: 1H-NMR(400.0 MHz, d6-DMSO): N-[4-[(2- 4.15[b] = 7.827 (2.4); 7.825 (2.5); 7.808 (2.6); 7.806 (2.7); cyanophenyl)methyl]-2,5- 7.625 (1.6); 7.622 (1.6); 7.606 (3.1); 7.603 (3.1); dimethylphenyl]-N-ethyl- 7.586 (2.0); 7.584 (1.9); 7.421 (1.6); 7.402 (2.7); N-methylmethanimidamide 7.383 (1.2); 7.153 (2.7); 7.134 (2.5); 6.749 (5.4); 6.604 (3.8); 4.042 (9.7); 3.319 (60.2); 2.917 (4.1); 2.670 (0.4); 2.666 (0.4); 2.505 (55.1); 2.501 (73.1); 2.497 (58.4); 2.328 (0.4); 2.114 (16.0); 2.080 (15.6); 1.398 (1.1); 1.133 (4.7); 1.116 (9.7); 1.098 (4.5); 0.000 (15.6) 9 1.79[a]; Example 9: 1H-NMR(400.0 MHz, d6-DMSO): N-[4-[(2,4- 4.86[b] = 7.585 (0.5); 7.214 (1.0); 7.208 (1.0); 7.188 (1.5); difluorophenyl)methyl]-2,5- 7.184 (1.5); 7.164 (1.0); 7.158 (1.0); 7.074 (0.5); dimethylphenyl]-N-ethyl- 7.053 (1.5); 7.035 (1.7); 7.014 (1.1); 7.006 (1.3); N-methylmethanimidamide 7.000 (1.2); 6.984 (1.8); 6.978 (1.7); 6.963 (0.6); 6.957 (0.6); 6.774 (4.9); 6.574 (3.6); 3.805 (7.5); 3.319 (38.3); 2.912 (3.9); 2.670 (0.3); 2.505 (44.3); 2.501 (59.0); 2.497 (45.0); 2.328 (0.3); 2.202 (0.6); 2.109 (16.0); 2.080 (15.1); 1.988 (0.4); 1.398 (1.1); 1.130 (4.7); 1.112 (9.6); 1.094 (4.5); 0.000 (0.6) 10 1.60[a]; Example 10: 1H-NMR(400.0 MHz, d6-DMSO): N-ethyl-N-[4-[(2- 4.87[b] = 7.584 (0.5); 7.268 (0.4); 7.264 (0.4); 7.249 (1.1); fluorophenyl)methyl]-2,5- 7.230 (1.6); 7.225 (1.0); 7.216 (0.8); 7.211 (0.8); dimethylphenyl]-N- 7.172 (1.7); 7.150 (1.8); 7.147 (1.8); 7.129 (1.1); methylmethanimidamide 7.126 (1.1); 7.109 (1.2); 7.107 (1.2); 7.091 (2.6); 7.088 (2.5); 7.072 (1.6); 7.070 (1.6); 7.039 (1.2); 7.035 (1.2); 7.020 (1.8); 7.016 (1.8); 7.001 (0.8); 6.997 (0.7); 6.926 (0.4); 6.787 (4.9); 6.572 (3.7); 6.555 (0.4); 5.753 (0.8); 3.836 (8.1); 3.751 (0.4); 3.317 (31.6); 2.912 (4.2); 2.523 (0.7); 2.510 (17.2); 2.506 (36.0); 2.501 (50.4); 2.496 (38.2); 2.492 (18.9); 2.202 (1.9); 2.118 (16.0); 2.079 (15.5); 2.033 (0.9); 1.988 (1.0); 1.960 (1.0); 1.398 (2.9); 1.175 (0.5); 1.130 (5.0); 1.113 (10.7); 1.095 (4.9); 0.008 (0.9); 0.000 (27.5); 0.008 (1.0) 11 1.58[a]; Example 11: 1H-NMR(400.0 MHz, d6-DMSO): N-(4-benzyl-2,5- 4.90[b] = 7.570 (0.4); 7.271 (1.6); 7.253 (4.4); 7.234 (3.4); dimethylphenyl)-N-ethyl- 7.217 (0.4); 7.164 (1.3); 7.146 (2.1); 7.128 (1.0); N-methylmethanimidamide 7.116 (3.6); 7.098 (3.1); 7.075 (0.3); 6.855 (4.2); 6.694 (0.4); 6.546 (3.1); 6.401 (0.5); 4.558 (0.5); 3.833 (7.2); 3.749 (0.8); 3.318 (22.6); 2.910 (3.6); 2.523 (0.6); 2.509 (11.1); 2.505 (23.3); 2.500 (32.6); 2.496 (24.5); 2.491 (11.9); 2.202 (0.7); 2.095 (16.0); 2.011 (1.5); 1.979 (1.5); 1.128 (4.4); 1.111 (9.6); 1.093 (4.3); 0.008 (0.6); 0.000 (19.2); 0.008 (0.7) 12 1.92[a]; Example 12: 1H-NMR(400.0 MHz, d6-DMSO): N-[4-[(2,4- 5.31[b] = 7.650 (0.5); 7.214 (1.0); 7.207 (1.0); 7.188 (1.4); difluorophenyl)methyl]-2,5- 7.183 (1.5); 7.164 (1.0); 7.158 (1.0); 7.074 (0.6); dimethylphenyl]-N- 7.053 (1.6); 7.036 (1.6); 7.014 (1.1); 7.005 (1.3); isopropyl-N- 6.999 (1.3); 6.984 (1.8); 6.978 (1.7); 6.963 (0.7); methylmethanimidamide 6.956 (0.6); 6.774 (4.9); 6.575 (3.5); 3.804 (7.4); 3.720 (0.4); 3.318 (40.6); 2.818 (14.0); 2.670 (0.4); 2.524 (0.9); 2.510 (23.9); 2.506 (50.3); 2.501 (70.3); 2.497 (53.3); 2.492 (26.4); 2.332 (0.3); 2.328 (0.4); 2.324 (0.3); 2.203 (0.6); 2.157 (0.4); 2.110 (16.0); 2.079 (15.1); 2.023 (0.8); 1.961 (0.8); 1.398 (0.3); 1.172 (8.3); 1.156 (8.3); 0.000 (0.8) 13 1.85[a] Example 13: 1H-NMR(400.0 MHz, d6-DMSO): N-[2,5-dimethyl-4-(1- = 7.601 (0.5); 7.204 (2.2); 7.186 (4.9); 7.166 (3.7); phenylcyclopropyl)phenyl]- 7.090 (1.9); 7.075 (6.5); 7.053 (1.1); 6.936 (4.8); N-ethyl-N- 6.918 (4.2); 6.903 (0.4); 6.554 (3.8); 3.322 (35.8); methylmethanimidamide 2.922 (4.4); 2.506 (43.1); 2.501 (57.6); 2.497 (43.1); 2.328 (0.3); 2.149 (15.5); 2.064 (16.0); 2.024 (0.6); 1.989 (0.6); 1.398 (4.1); 1.292 (1.3); 1.275 (4.6); 1.266 (2.0); 1.225 (0.6); 1.186 (1.9); 1.177 (4.5); 1.173 (4.1); 1.161 (1.3); 1.136 (5.4); 1.119 (11.4); 1.101 (5.2); 0.008 (1.5); 0.000 (32.6) 14 1.63[a] Example 14: 1H-NMR(400.0 MHz, d6-DMSO): N-[4-(2,2-difluoro-1- = 7.594 (0.4); 7.335 (1.3); 7.318 (9.8); 7.301 (4.8); phenylcyclopropyl)-2,5- 7.281 (1.6); 7.268 (0.4); 7.264 (0.3); 7.249 (1.0); dimethylphenyl]-N-ethyl- 7.235 (1.2); 7.230 (2.0); 7.224 (1.0); 7.220 (1.0); N-methylmethanimidamide 7.214 (1.8); 7.203 (4.2); 7.182 (0.7); 7.163 (0.6); 6.554 (2.9); 3.365 (0.4); 3.323 (48.2); 2.908 (2.9); 2.523 (0.8); 2.510 (19.3); 2.505 (39.8); 2.501 (52.9); 2.496 (38.0); 2.492 (18.3); 2.445 (0.5); 2.423 (0.7); 2.411 (0.5); 2.402 (0.5); 2.390 (0.4); 2.328 (0.3); 2.300 (2.5); 2.162 (16.0); 2.158 (15.9); 2.080 (0.4); 2.031 (0.7); 2.019 (0.5); 2.010 (0.5); 1.998 (0.9); 1.985 (0.6); 1.976 (0.5); 1.965 (0.4); 1.883 (0.5); 1.398 (7.1); 1.124 (4.7); 1.107 (10.0); 1.089 (4.5); 0.008 (1.8); 0.000 (48.7); 0.008 (2.1) 15 1.83[a] Example 15: 1H-NMR(400.0 MHz, d6-DMSO): N-[4-(2,2-dichloro-1- = 7.594 (0.9); 7.541 (0.6); 7.493 (7.2); 7.474 (8.7); phenylcyclopropyl)-2,5- 7.327 (4.5); 7.308 (9.0); 7.289 (5.3); 7.222 (3.4); dimethylphenyl]-N-ethyl- 7.204 (4.8); 7.185 (1.8); 6.520 (1.4); 5.755 (4.0); N-methylmethanimidamide 3.322 (58.4); 2.904 (7.0); 2.775 (0.5); 2.671 (0.9); 2.501 (125.5); 2.422 (0.6); 2.395 (0.6); 2.364 (0.6); 2.328 (1.4); 2.174 (8.5); 2.092 (1.3); 2.073 (1.2); 1.481 (0.4); 1.467 (0.4); 1.298 (0.3); 1.258 (0.6); 1.235 (1.1); 1.150 (0.4); 1.119 (7.8); 1.101 (16.0); 1.083 (7.7); 1.012 (0.4); 0.995 (0.4); 0.000 (61.9) 16 1.89[a] Example 16: 1H-NMR(400.0 MHz, d6-DMSO): N-[4-(2,2-dibromo-1- = 7.501 (7.0); 7.482 (7.7); 7.321 (3.2); 7.302 (6.4); phenylcyclopropyl)-2,5- 7.283 (3.8); 7.213 (3.0); 7.194 (4.2); 7.176 (1.7); dimethylphenyl]-N-ethyl- 6.460 (0.8); 5.754 (12.8); 3.319 (25.2); 2.894 (5.6); N-methylmethanimidamide 2.673 (0.4); 2.669 (0.5); 2.664 (0.4); 2.522 (2.0); 2.509 (30.6); 2.504 (62.0); 2.500 (82.3); 2.495 (59.5); 2.491 (29.2); 2.331 (0.6); 2.327 (0.7); 2.322 (0.6); 2.277 (0.5); 2.251 (1.0); 2.197 (3.7); 2.148 (3.3); 2.081 (0.7); 1.234 (0.6); 1.149 (0.3); 1.112 (7.5); 1.095 (16.0); 1.077 (7.2); 0.008 (0.7); 0.000 (20.4); 0.009 (0.9) 18 1.58.sup.[a]; Example 18: 1H-NMR(400.0 MHz, d6-DMSO): N-[5-chloro-2-methyl-4-(1- 5.32.sup.[b] = 7.6983 (0.9); 7.5942 (0.4); 7.2863 (1.9); 7.2674 phenylethyl)phenyl]-N- (5.1); 7.2493 (4.8); 7.2152 (6.3); 7.1973 (3.3); 7.1716 ethyl-N- (1.8); 7.1539 (2.6); 7.1391 (0.7); 7.1360 (1.0); 7.0963 methylmethanimidamide (5.7); 6.8146 (1.7); 5.7559 (1.1); 4.4578 (0.6); 4.4399 (2.1); 4.4219 (2.2); 4.4039 (0.6); 3.4069 (0.5); 3.3240 (8.2); 2.9586 (1.2); 2.9011 (3.2); 2.5051 (12.6); 2.5008 (16.0); 2.4964 (11.4); 2.1331 (16.0); 1.5393 (9.3); 1.5212 (9.1); 1.3964 (2.8); 1.1283 (3.5); 1.1107 (6.7); 1.0931 (3.3) 19 1.58.sup.[a]; Example 19: 1H-NMR(400.0 MHz, d6-DMSO): N-[5-chloro-2-methyl-4-(1- 5.24.sup.[b] = 7.7935 (1.3); 7.6874 (0.5); 7.3394 (1.1); 7.3348 phenylethen-1-yl)phenyl]- (1.7); 7.3309 (0.9); 7.3183 (4.9); 7.3137 (3.0); 7.2998 N-ethyl-N- (5.8); 7.2889 (1.5); 7.2848 (3.0); 7.2810 (2.4); 7.2744 methylmethanimidamide (1.1); 7.2678 (3.1); 7.2587 (0.9); 7.2497 (6.2); 7.2456 (6.6); 7.2329 (2.2); 7.2290 (4.2); 7.0860 (0.5); 7.0654 (0.7); 7.0482 (6.5); 6.8999 (1.7); 6.8479 (0.8); 6.8309 (0.6); 5.8120 (5.5); 5.8099 (5.5); 5.2060 (5.6); 5.2041 (5.5); 3.4443 (0.7); 3.4067 (0.4); 3.3682 (1.4); 3.3510 (1.5); 3.3201 (32.5); 3.0015 (1.7); 2.9390 (4.3); 2.6707 (0.4); 2.5233 (1.5); 2.5099 (25.7); 2.5057 (51.6); 2.5013 (67.7); 2.4968 (48.9); 2.3327 (0.4); 2.3281 (0.4); 2.1771 (16.0); 2.1377 (3.1); 1.3973 (0.5); 1.1573 (3.6); 1.1398 (7.5); 1.1224 (4.1); 0.0002 (6.4) 20 2.00.sup.[a]; Example 20: 1H-NMR(400.0 MHz, d6-DMSO): N-(4-benzyl-5-fluoro-2- 4.62.sup.[b] = 7.6963 (1.0); 7.5952 (0.4); 7.2864 (2.2); 7.2676 methylphenyl)-N-ethyl-N- (5.4); 7.2492 (5.3); 7.2320 (0.6); 7.1908 (6.7); 7.1848 methylmethanimidamide (3.8); 7.1716 (4.5); 7.1645 (3.7); 7.1461 (1.5); 6.9778 (3.1); 6.9556 (3.0); 6.6402 (1.0); 6.6110 (1.1); 6.3658 (0.4); 6.3352 (0.4); 4.9662 (0.6); 3.8334 (10.1); 3.7380 (1.0); 3.4108 (0.6); 3.3228 (10.2); 2.9568 (1.3); 2.9056 (3.3); 2.5053 (21.2); 2.5010 (26.7); 2.4968 (19.8); 2.0954 (16.0); 1.9625 (1.9); 1.1320 (3.6); 1.1144 (7.2); 1.0968 (3.6) 21 1.86.sup.[a]; Example 21: 1H-NMR(400.0 MHz, d6-DMSO): N-[2-chloro-4-[(2,4- 4.60.sup.[b] = 7.7077 (1.2); 7.5939 (0.5); 7.2451 (0.9); 7.2386 difluorophenyl)methyl]-5- (0.9); 7.2188 (1.4); 7.2151 (1.4); 7.1955 (1.0); 7.1892 methylphenyl]-N-ethyl-N- (1.0); 7.1512 (0.6); 7.1297 (1.5); 7.1123 (1.5); 7.0912 methylmethanimidamide (0.8); 7.0422 (1.0); 7.0369 (1.0); 7.0210 (1.6); 7.0157 (1.5); 6.9997 (0.7); 6.9943 (0.7); 6.9796 (5.3); 6.8071 (1.6); 3.8453 (7.2); 3.4173 (0.6); 3.3393 (1.3); 3.3200 (25.4); 2.9789 (1.5); 2.9128 (3.8); 2.6708 (0.4); 2.5061 (51.6); 2.5017 (63.8); 2.4973 (46.8); 2.3285 (0.4); 2.2292 (0.4); 2.1423 (16.0); 1.1446 (2.3); 1.1277 (4.4); 1.1106 (2.4); 0.0002 (0.5) 22 1.63.sup.[a] Example 22: 1H-NMR(400.0 MHz, d6-DMSO): N-[5-chloro-4-[(2,4- = 7.7285 (1.1); 7.6207 (0.4); 7.2264 (1.1); 7.2199 difluorophenyl)methyl]-2- (1.2); 7.2015 (1.7); 7.1954 (2.2); 7.1770 (1.2); 7.1705 methylphenyl]-N-ethyl-N- (1.2); 7.1503 (0.8); 7.1289 (1.9); 7.1103 (2.2); 7.0901 methylmethanimidamide (1.1); 7.0257 (1.4); 7.0195 (1.4); 7.0082 (1.5); 7.0044 (1.6); 7.0017 (1.7); 6.9863 (1.1); 6.9796 (1.1); 6.9659 (5.8); 6.8807 (1.6); 5.7558 (3.7); 4.0390 (0.7); 4.0212 (0.7); 3.9230 (8.9); 3.4156 (0.6); 3.3420 (1.3); 3.3221 (7.3); 2.9767 (1.4); 2.9104 (3.6); 2.5115 (10.2); 2.5073 (19.8); 2.5028 (26.1); 2.4984 (19.6); 2.4943 (10.1); 2.1417 (0.8); 2.1078 (16.0); 1.9893 (2.8); 1.3974 (7.7); 1.1935 (0.8); 1.1757 (1.5); 1.1578 (0.9); 1.1382 (2.7); 1.1212 (5.1); 1.1041 (2.7); 0.0078 (0.7); 0.0002 (17.5); 0.0079 (0.8) 23 1.66.sup.[a]; Example 23: 1H-NMR(400.0 MHz, d6-DMSO): N-[5-chloro-2-methyl-4- 5.54.sup.[b] = 7.7422 (0.8); 7.1857 (1.0); 7.1802 (1.2); 7.1641 [(2-methylphenyl)methyl] (2.1); 7.1383 (0.6); 7.1339 (0.7); 7.1200 (2.0); 7.1150 phenyl]-N-ethyl-N- (2.2); 7.1047 (2.9); 7.0946 (1.9); 7.0895 (1.6); 7.0757 methylmethanimidamide (0.6); 7.0715 (0.5); 6.8889 (2.6); 6.8726 (1.9); 6.8672 (1.6); 6.7643 (4.6); 5.7551 (0.6); 3.8983 (8.5); 3.8046 (0.3); 3.4136 (0.5); 3.3504 (0.9); 3.3202 (9.7); 2.9807 (1.0); 2.9113 (2.5); 2.5055 (29.5); 2.5013 (38.1); 2.4970 (28.7); 2.2290 (16.0); 2.1408 (0.5); 2.0678 (12.7); 1.9883 (0.6); 1.9409 (0.6); 1.3976 (2.7); 1.1747 (0.3); 1.1563 (0.4); 1.1416 (1.9); 1.1246 (3.6); 1.1078 (2.1); 0.0075 (0.7); 0.0002 (17.6) 24 1.63.sup.[a]; Example 24: 1H-NMR(400.0 MHz, d6-DMSO): N-[5-chloro-4-[(2,3- 4.92.sup.[b] = 7.7338 (1.1); 7.6249 (0.4); 7.3091 (0.5); 7.3056 difluorophenyl)methyl]-2- (0.5); 7.2849 (1.3); 7.2633 (1.3); 7.2426 (0.7); 7.2392 methylphenyl]-N-ethyl-N- (0.6); 7.1459 (0.7); 7.1420 (0.7); 7.1326 (0.7); 7.1259 methylmethanimidamide (1.3); 7.1221 (1.3); 7.1125 (1.2); 7.1090 (1.4); 7.1018 (0.7); 7.0924 (0.6); 7.0889 (0.6); 7.0108 (5.5); 6.9130 (1.2); 6.8935 (3.0); 6.8777 (1.9); 4.0024 (9.0); 3.4151 (0.6); 3.3438 (1.3); 3.3220 (45.8); 2.9803 (1.3); 2.9114 (3.5); 2.6753 (0.3); 2.6708 (0.5); 2.6663 (0.3); 2.5241 (1.2); 2.5063 (64.3); 2.5020 (83.8); 2.4976 (60.1); 2.3330 (0.4); 2.3288 (0.5); 2.3244 (0.4); 2.1152 (16.0); 1.1395 (2.4); 1.1222 (4.7); 1.1051 (2.6); 0.0077 (1.8); 0.0002 (48.7); 0.0083 (1.9) 25 2.05.sup.[a]; Example 25: 1H-NMR(400.0 MHz, d6-DMSO): = N-[5-chloro-2-methyl-4- 6.02.sup.[b] 7.7120 (0.9); 7.6035 (0.4); 7.4517 (1.8); 7.4345 (5.2); [(2-phenylphenyl)methyl] 7.4157 (4.7); 7.3876 (2.4); 7.3752 (0.8); 7.3697 (2.8); phenyl]-N-ethyl-N- 7.3627 (0.6); 7.3513 (0.8); 7.3200 (4.7); 7.3162 (5.7); methylmethanimidamide 7.2991 (4.7); 7.2929 (4.3); 7.2840 (3.6); 7.2788 (3.9); 7.2701 (5.3); 7.2603 (0.9); 7.2389 (0.6); 7.2289 (2.9); 7.2200 (2.1); 7.2153 (1.6); 7.2062 (1.5); 7.0425 (0.4); 7.0339 (2.0); 7.0231 (1.7); 7.0200 (1.8); 7.0113 (1.8); 6.8164 (1.5); 6.7179 (5.8); 3.8752 (10.6); 3.4058 (0.6); 3.3222 (43.7); 2.9683 (1.2); 2.9001 (3.1); 2.6708 (0.5); 2.6664 (0.4); 2.5238 (1.4); 2.5061 (71.3); 2.5018 (91.3); 2.4975 (65.1); 2.3330 (0.4); 2.3286 (0.5); 2.0571 (16.0); 1.9885 (0.8); 1.3976 (11.6); 1.1748 (0.4); 1.1309 (2.5); 1.1140 (4.9); 1.0967 (2.6); 0.0079 (1.9); 0.0002 (51.6); 0.0084 (2.0) 26 1.53.sup.[a]; Example 26: 1H-NMR(400.0 MHz, d6-DMSO): N-[2-chloro-4-[(2- 4.45.sup.[b] = 7.7010 (0.6); 7.2282 (0.5); 7.2199 (0.5); 7.2137 methoxyphenyl)methyl]-5- (0.6); 7.2065 (0.9); 7.2000 (0.6); 7.1927 (0.8); 7.1848 methylphenyl]-N-ethyl-N- (0.7); 7.0002 (2.0); 6.9797 (1.6); 6.9035 (4.1); 6.8754 methylmethanimidamide (0.4); 6.8648 (4.0); 6.8571 (1.9); 6.8503 (1.6); 6.7849 (1.0); 5.7567 (0.4); 3.7833 (16.0); 3.7761 (6.4); 3.3364 (0.7); 3.3230 (8.6); 2.9744 (0.8); 2.9100 (2.0); 2.5097 (6.0); 2.5055 (12.3); 2.5010 (16.4); 2.4966 (11.8); 2.4924 (5.7); 2.1333 (11.0); 1.3971 (0.6); 1.1431 (1.5); 1.1255 (3.1); 1.1079 (1.6); 0.0002 (8.5) 27 1.61.sup.[a]; Example 27: 1H-NMR(400.0 MHz, d6-DMSO): N-[2-chloro-5-methyl-4-(1- 4.70.sup.[b] = 7.6897 (0.9); 7.5799 (0.3); 7.2897 (1.7); 7.2689 phenylethyl)phenyl]-N- (3.7); 7.2579 (0.9); 7.2518 (3.5); 7.1758 (7.2); 7.1574 ethyl-N- (5.7); 7.1505 (6.5); 7.1418 (0.8); 7.1387 (0.9); 6.7447 methylmethanimidamide (1.4); 4.2427 (0.4); 4.2248 (1.6); 4.2069 (1.6); 4.1889 (0.5); 3.4202 (0.4); 3.4131 (0.4); 3.3221 (17.9); 2.9676 (1.1); 2.9082 (3.0); 2.5233 (0.4); 2.5099 (12.2); 2.5055 (25.4); 2.5011 (33.7); 2.4966 (23.9); 2.4923 (11.3); 2.1163 (16.0); 1.5051 (7.0); 1.4872 (7.0); 1.3973 (1.1); 1.1380 (2.8); 1.1203 (5.8); 1.1025 (2.8); 0.0079 (0.6); 0.0002 (18.3); 0.0086 (0.6) 28 1.63.sup.[a]; Example 28: 1H-NMR(400.0 MHz, d6-DMSO): = N-[2-chloro-4-[(2- 4.93.sup.[b] 7.7254 (1.1); 7.6110 (0.4); 7.4875 (1.7); 7.4769 (1.3); chlorophenyl)methyl]-5- 7.4729 (1.7); 7.4643 (2.2); 7.4542 (0.4); 7.2998 (0.5); methylphenyl]-N-ethyl-N- 7.2894 (4.2); 7.2806 (2.9); 7.2753 (3.2); 7.2661 (4.0); methylmethanimidamide 7.2565 (0.5); 7.0545 (1.6); 7.0455 (1.5); 7.0415 (1.3); 7.0311 (1.3); 6.8502 (6.0); 6.8354 (1.5); 3.9433 (8.7); 3.4196 (0.5); 3.3464 (1.0); 3.3243 (13.9); 2.9851 (1.3); 2.9165 (3.4); 2.5240 (0.4); 2.5064 (18.9); 2.5020 (24.4); 2.4976 (17.3); 2.1350 (16.0); 1.3971 (0.6); 1.1486 (2.0); 1.1312 (3.9); 1.1139 (2.1); 0.0078 (0.4); 0.0002 (10.8); 0.0086 (0.4) 29 1.58.sup.[a]; Example 29: 1H-NMR(400.0 MHz, d6-DMSO): = N-[5-chloro-4-+(2- 4.95.sup.[b] 7.7263 (0.5); 7.2147 (0.5); 7.2056 (0.5); 7.2011 (0.7); methoxyphenyl)methyl]-2- 7.1933 (0.9); 7.1857 (0.6); 7.1801 (0.8); 7.1715 (0.7); methylphenyl]-N-ethyl-N- 6.9889 (2.1); 6.9685 (1.6); 6.8819 (3.5); 6.8618 (0.9); methylmethanimidamide 6.8546 (1.0); 6.8441 (4.7); 6.8354 (2.2); 6.8307 (2.0); 3.8692 (6.6); 3.7938 (16.0); 3.3438 (0.6); 3.3213 (14.8); 2.9739 (0.6); 2.9088 (1.6); 2.5236 (0.5); 2.5099 (14.2); 2.5057 (29.3); 2.5012 (39.0); 2.4968 (28.0); 2.4927 (13.6); 2.0829 (9.6); 1.1387 (1.4); 1.1213 (2.8); 1.1039 (1.5); 0.0002 (5.7) 30 1.81.sup.[a]; Example 30: 1H-NMR(400.0 MHz, d6-DMSO): = N-[5-chloro-4-[(2- 5.55.sup.[b] 7.7501 (1.1); 7.6411 (0.6); 7.4724 (2.1); 7.4632 (2.1); chlorophenyl)methyl]-2- 7.4579 (2.2); 7.4493 (2.6); 7.2827 (0.9); 7.2727 (5.1); methylphenyl]-N-ethyl-N- 7.2640 (4.4); 7.2581 (4.5); 7.2494 (5.0); 7.2402 (0.7); methylmethanimidamide 7.0383 (0.5); 7.0288 (2.1); 7.0197 (1.9); 7.0144 (1.8); 7.0052 (1.7); 6.9097 (1.6); 6.8677 (5.8); 4.0295 (11.5); 3.4165 (0.8); 3.3208 (229.2); 2.9798 (1.4); 2.9665 (0.9); 2.9146 (3.5); 2.6703 (3.1); 2.6100 (0.4); 2.5055 (412.8); 2.5012 (531.9); 2.4969 (384.4); 2.3279 (3.0); 2.0912 (16.0); 1.2330 (0.5); 1.1422 (2.4); 1.1267 (4.5); 1.1100 (2.7); 1.0875 (0.4); 0.1465 (0.5); 0.0078 (4.4); 0.0002 (118.1); 0.0083 (5.1); 0.1492 (0.5) 31 1.66.sup.[a]; Example 31: 1H-NMR(400.0 MHz, d6-DMSO): N-[2-chloro-5-methyl-4-(1- 4.93.sup.[b] = 7.7789 (1.5); 7.6677 (0.7); 7.3558 (1.2); 7.3390 phenylethen-1-yl)phenyl]- (3.7); 7.3204 (4.3); 7.3076 (2.4); 7.2908 (1.9); 7.2719 N-ethyl-N- (0.6); 7.2484 (4.8); 7.2315 (3.5); 7.0846 (6.0); 6.8436 methylmethanimidamide (1.9); 5.7855 (4.3); 5.1762 (4.3); 3.4620 (0.6); 3.4452 (0.8); 3.3665 (1.7); 3.3265 (170.4); 3.0056 (2.0); 2.9439 (4.9); 2.6711 (1.0); 2.5055 (136.5); 2.5016 (169.0); 2.4979 (131.0); 2.3281 (1.0); 1.8954 (16.0); 1.1638 (2.9); 1.1467 (5.9); 1.1290 (2.9); 0.0001 (2.2) 32 1.46.sup.[a]; Example 32: 1H-NMR(400.0 MHz, d6-DMSO): N-ethyl-N-[5-fluoro-4-[(2- 4.34.sup.[b] = 7.7009 (0.4); 7.2062 (0.5); 7.2017 (0.6); 7.1829 methoxyphenyl)methyl]-2- (1.0); 7.1672 (0.7); 7.1629 (0.8); 6.9728 (1.6); 6.9528 methylphenyl]-N- (2.3); 6.9335 (1.3); 6.8575 (2.2); 6.8415 (1.7); 6.8392 methylmethanimidamide (1.8); 6.8347 (1.5); 6.8231 (0.7); 6.8211 (0.7); 6.6329 (0.5); 6.6026 (0.5); 3.7854 (16.0); 3.7787 (5.8); 3.3232 (66.9); 2.9542 (0.5); 2.9073 (1.3); 2.5237 (0.7); 2.5187 (1.2); 2.5103 (17.9); 2.5059 (37.1); 2.5014 (49.4); 2.4969 (35.4); 2.4925 (17.2); 2.0728 (7.6); 1.9884 (0.8); 1.9433 (0.4); 1.3978 (4.2); 1.1746 (0.4); 1.1349 (1.5); 1.1173 (3.1); 1.0998 (1.6); 0.0002 (6.1) 33 1.41.sup.[a]; Example 33: 1H-NMR(400.0 MHz, d6-DMSO): N-ethyl-N-[5-fluoro-4-[(2- 4.37.sup.[b] = 7.7033 (1.0); 7.6009 (0.4); 7.2818 (0.5); 7.2773 fluorophenyl)methyl]-2- (0.5); 7.2680 (0.6); 7.2629 (1.3); 7.2435 (1.8); 7.2389 methylphenyl]-N- (1.2); 7.2300 (0.9); 7.2251 (1.0); 7.2041 (0.9); 7.1867 methylmethanimidamide (2.1); 7.1676 (3.3); 7.1419 (2.3); 7.1336 (2.7); 7.1210 (1.6); 7.1153 (3.1); 7.0968 (1.2); 7.0943 (1.1); 6.9233 (2.8); 6.9012 (2.8); 6.6512 (1.0); 6.6229 (1.1); 4.0379 (0.4); 4.0203 (0.4); 3.8584 (9.1); 3.7610 (0.4); 3.4093 (0.5); 3.3210 (28.0); 2.9605 (1.2); 2.9058 (3.3); 2.6706 (0.3); 2.5102 (20.8); 2.5060 (41.4); 2.5015 (54.4); 2.4970 (39.4); 2.4928 (19.5); 2.0861 (16.0); 1.9886 (1.5); 1.9541 (0.7); 1.3974 (10.0); 1.1926 (0.4); 1.1748 (0.8); 1.1570 (0.5); 1.1330 (3.2); 1.1155 (6.2); 1.0980 (3.2); 0.0002 (6.9) 34 1.55.sup.[a]; Example 34: 1H-NMR(400.0 MHz, d6-DMSO): N-ethyl-N-[5-fluoro-2- 4.63.sup.[b] = 7.6807 (0.9); 7.5811 (0.3); 7.2860 (1.8); 7.2668 methyl-4-(1- (5.4); 7.2490 (6.0); 7.2248 (6.9); 7.2076 (3.0); 7.1740 phenylethyl)phenyl]-N- (1.4); 7.1703 (1.9); 7.1666 (1.1); 7.1527 (3.0); 7.1388 methylmethanimidamide (0.8); 7.1351 (1.3); 7.0449 (2.9); 7.0228 (2.9); 6.5861 (1.1); 6.5557 (1.1); 4.9435 (0.5); 4.2982 (0.6); 4.2804 (2.2); 4.2623 (2.2); 4.2440 (0.7); 3.4019 (0.5); 3.3192 (67.6); 2.9907 (0.3); 2.9211 (2.0); 2.9015 (3.0); 2.6744 (0.6); 2.6698 (0.8); 2.6654 (0.6); 2.5232 (2.0); 2.5097 (49.0); 2.5053 (101.8); 2.5009 (135.8); 2.4963 (98.5); 2.4920 (48.6); 2.3320 (0.6); 2.3275 (0.8); 2.3231 (0.6); 2.1170 (16.0); 1.9878 (1.3); 1.9838 (1.5); 1.5459 (9.9); 1.5277 (9.9); 1.4982 (0.9); 1.4799 (0.8); 1.3975 (8.1); 1.1743 (0.5); 1.1563 (0.4); 1.1275 (4.3); 1.1098 (8.2); 1.0921 (3.9); 0.0077 (0.5); 0.0004 (16.0); 0.0084 (0.7) 35 1.52.sup.[a]; Example 35: 1H-NMR(400.0 MHz, d6-DMSO): N-[4-[(2,4- 4.54.sup.[b] = 7.7043 (1.0); 7.6008 (0.4); 7.3496 (0.4); 7.3287 difluorophenyl)methyl]-5- (0.4); 7.2552 (0.8); 7.2338 (1.8); 7.2165 (1.9); 7.2103 fluoro-2-methylphenyl]-N- (2.1); 7.2032 (1.4); 7.1949 (1.1); 7.1842 (1.8); 7.1790 ethyl-N- (1.8); 7.1602 (1.2); 7.1539 (1.3); 7.0339 (1.0); 7.0286 methylmethanimidamide (1.0); 7.0127 (1.9); 7.0074 (1.8); 6.9915 (0.9); 6.9862 (0.8); 6.9192 (2.8); 6.8969 (2.8); 6.6535 (1.0); 6.6234 (1.1); 3.8318 (8.6); 3.4124 (0.6); 3.3184 (55.2); 2.9622 (1.3); 2.9206 (2.2); 2.9055 (3.4); 2.6749 (0.7); 2.6703 (1.0); 2.6659 (0.7); 2.5234 (3.1); 2.5100 (61.0); 2.5058 (123.5); 2.5013 (163.4); 2.4968 (119.1); 2.4926 (59.3); 2.3327 (0.7); 2.3280 (1.0); 2.3235 (0.7); 2.1332 (1.6); 2.0877 (16.0); 1.9884 (0.8); 1.9548 (0.4); 1.3977 (3.2); 1.1747 (0.4); 1.1569 (0.4); 1.1334 (3.5); 1.1158 (6.3); 1.0984 (3.2); 0.1459 (0.9); 0.0078 (7.9); 0.0002 (199.2); 0.0084 (9.3); 0.1497 (0.9) .sup.[a]LogP value is determined by measurement of LC-UV, in an acidic range, with 0.1% formic acid in water and acetonitrile as eluent (linear gradient from 10% acetonitrile to 95% acetonitrile). .sup.[b]LogP value is determined by measurement of LC-UV, in a neutral range, with 0.001 molar ammonium acetate solution in water and acetonitrile as eluent (linear gradient from 10% acetonitrile to 95% acetonitrile). .sup.[c]LogP value is determined by measurement of LC-UV, in an acidic range, with 0.1% phosphoric acid and acetonitrile as eluent (linear gradient from 10% acetonitrile to 95% acetonitrile).
Log P Measurement
[0306] Measurement of Log P values was performed according to EEC directive 79/831 Annex V.A8 by HPLC (High Performance Liquid Chromatography) on reversed phase columns with the following methods:
[0307] If more than one Log P value is available within the same method, all the values are given and separated by +.
[0308] Calibration was done with straight-chain alkan2-ones (with 3 to 16 carbon atoms) with known Log P values (measurement of Log P values using retention times with linear interpolation between successive alkanones). Lambda-max-values were determined using UV-spectra from 200 nm to 400 nm and the peak values of the chromatographic signals.
NMR-Peak Lists
[0309] 1H-NMR data of selected examples are written in form of 1H-NMR-peak lists. To each signal peak are listed the -value in ppm and the signal intensity in round brackets. Between the -valuesignal intensity pairs are semicolons as delimiters.
[0310] The peak list of an example has therefore the form:
[0311] .sub.1 (intensity.sub.1; .sub.2 (intensity.sub.2); . . . ; .sub.i (intensity.sub.i); . . . ; .sub.n (intensity.sub.n)
[0312] Intensity of sharp signals correlates with the height of the signals in a printed example of a NMR spectrum in cm and shows the real relations of signal intensities. From broad signals several peaks or the middle of the signal and their relative intensity in comparison to the most intensive signal in the spectrum can be shown.
[0313] For calibrating chemical shift for 1H spectra, we use tetramethylsilane and/or the chemical shift of the solvent used, especially in the case of spectra measured in DMSO. Therefore in NMR peak lists, tetramethylsilane peak can occur but not necessarily.
[0314] The 1H-NMR peak lists are similar to classical 1H-NMR prints and contains therefore usually all peaks, which are listed at classical NMR-interpretation.
[0315] Additionally they can show like classical 1H-NMR prints signals of solvents, stereoisomers of the target compounds, which are also object of the invention, and/or peaks of impurities.
[0316] To show compound signals in the delta-range of solvents and/or water the usual peaks of solvents, for example peaks of DMSO in DMSO-D.sub.6 and the peak of water are shown in our 1H-NMR peak lists and have usually on average a high intensity.
[0317] The peaks of stereoisomers of the target compounds and/or peaks of impurities have usually on average a lower intensity than the peaks of target compounds (for example with a purity>90%).
[0318] Such stereoisomers and/or impurities can be typical for the specific preparation process. Therefore their peaks can help to recognize the reproduction of our preparation process via side-products-fingerprints.
[0319] The present invention will be illustrated with the biological examples. However the invention is not limited to the examples.
Example: In Vivo Preventive Test on Phakopsora Test (Soybeans)
[0320]
TABLE-US-00003 Solvent: 24.5 parts by weight of acetone 24.5 parts by weight of dimethylacetamide Emulsifier: 1 part by weight of alkylaryl polyglycol ether
[0321] To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration.
[0322] To test for preventive activity, young plants are sprayed with the preparation of active compound at the stated rate of application. After the spray coating has dried on, the plants are inoculated with an aqueous spore suspension of the causal agent of soybean rust (Phakopsora pachyrhizi) and stay for 24 h without light in an incubation cabinet at approximately 24 C. and a relative atmospheric humidity of 95%.
[0323] The plants remain in the incubation cabinet at approximately 24 C. and a relative atmospheric humidity of approximately 80% and a day/night interval of 12 h.
[0324] The test is evaluated 7 days after the inoculation. 0% means an efficacy which corresponds to that of the untreated control, while an efficacy of 100% means that no disease is observed.
[0325] In this test the following compounds according to the invention showed efficacy between 80% and 89% at a concentration of 10 ppm of active ingredient: 1; 19
[0326] In this test the following compounds according to the invention showed efficacy between 90% and 100% at a concentration of 10 ppm of active ingredient: 2; 3; 6; 8; 9; 10; 11; 12; 13; 14; 18; 20; 21; 22; 23; 24; 30
