organic compounds
(Z)-4-Chloro-N-{3-[(4-chlorophenyl)sulfonyl]-2,3-dihydrobenzo[d]thiazol-2-ylidene}benzenesulfonamide
aDepartment of Chemistry and Biochemistry, Northern Illinois University, DeKalb, IL 60115, USA
*Correspondence e-mail: czheng@niu.edu
The title compound, C19H12Cl2N2O4S3, is related to a ditosylated 2-iminobenzothiazole with the two methyl groups on the two phenyl rings replaced by chlorine. There is a weak intramolecular π–π contact between the two phenyl rings, with a centroid-to-centroid distance of 4.004 (2) Å. The dihedral angle between the rings is 9.96 (13)°. An intramolecular C—H⋯O hydrogen bond stabilizes the molecular conformation.
Keywords: crystal structure; IspF inhibitor; bis-sulfonamide.
CCDC reference: 1555243
Structure description
The methylerythritolphosphate (MEP) pathway is an essential enzymatic pathway for the biosynthesis of isoprenoid precursors present in most bacteria, some protozoa and plants (Persch et al., 2015; Frank & Groll, 2017; Hunter, 2007; Masini & Hirsch, 2014; Odom, 2011; Hale et al., 2012). Inhibition of enzymes from this pathway has tremendous potential to generate new anti-infective agents or herbicides (Frank & Groll, 2017; Witschel et al., 2013). The enzyme 2-methylerythritol 2,4-cyclodiphosphate synthase (IspF) is present in the MEP pathway (Zhang et al., 2013, Geist et al., 2010, Crane et al., 2006). Recently, bis-sulfonamides of ortho-phenylenediamine have been shown to have micromolar inhibitory activity against IspF from Arabidopsis thaliana, Plasmodium falciparum, or Burkholderia pseudomallei (Thelemann et al., 2015). In our quest to discover inhibitors of IspF, we synthesized a series of sulfonamide and bis-sulfonamide analogs of 2-aminobenzthiazole that would be capable of binding to the zinc ion of the IspF enzyme. This work resulted in the synthesis of the title compound.
The title compound, shown in Fig. 1, is closely related to a ditosylated 2-iminobenzothiazole (Castanheiro et al., 2017) with the two methyl groups on the two phenyl groups replaced by chlorine. However, there are significant structural differences between the structures of the two compounds. The title compound crystallizes in the P, whereas the methyl compound crystallizes in P21/c. Furthermore, the phenyl rings of the title compound lie on one side of the iminobenzothiazole plane, whereas they are on the other side in the methyl compound, as shown in Fig. 2. The torsion angles C31—N32—S2—C24 and C31—N1—S1—C14 in the title compound are −57.91 (16) and −122.8 (2)°, respectively. The corresponding torsion angles of the methyl compound are 60.9 (2) and 107.2 (2)°, respectively. Weak non-classical hydrogen bonds of the type C—H⋯O (Table 1) consolidate the molecular packing in the crystal (Fig. 3).
Synthesis and crystallization
2-Aminobenzothiazole (0.98 mmol) was dissolved in methylene chloride (5 ml) and pyridine (3.8 mmol) in an ice bath. 4-Chlorobenzenesulfonyl chloride (1.0 mmol) was added while stirring, and the reaction was allowed to come to room temperature. The reaction was monitored by TLC, and after 18 h the mixture was concentrated and the remaining solution in pyridine was extracted with water (100 ml) and ethyl acetate (80 ml). The organic layer was washed with brine (30 ml) and dried over anhydrous sodium sulfate. The combined extracts were concentrated to obtain the crude product, which was chromatographed (1: 2 v/v ethyl acetate/hexane) to yield the title compound (0.11 mmol, 11%). The material was recrystallized from a CDCl3 solution.
Refinement
Crystal data, data collection and structure .
details are summarized in Table 2Structural data
CCDC reference: 1555243
https://doi.org/10.1107/S2414314617008653/wm4046sup1.cif
contains datablock I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314617008653/wm4046Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S2414314617008653/wm4046Isup3.mol
Supporting information file. DOI: https://doi.org/10.1107/S2414314617008653/wm4046Isup4.cml
Data collection: SMART (Bruker, 1999); cell
SAINT (Bruker, 1999); data reduction: SAINT (Bruker, 1999); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL2016 (Sheldrick, 2015); molecular graphics: XP in SHELXTL (Sheldrick, 2008) and Mercury (Macrae et al., 2006); software used to prepare material for publication: publCIF (Westrip, 2010).C19H12Cl2N2O4S3 | Z = 2 |
Mr = 499.39 | F(000) = 508 |
Triclinic, P1 | Dx = 1.628 Mg m−3 |
a = 7.1330 (9) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 8.1155 (11) Å | Cell parameters from 906 reflections |
c = 17.798 (2) Å | θ = 2–14° |
α = 87.747 (2)° | µ = 0.66 mm−1 |
β = 81.840 (2)° | T = 293 K |
γ = 87.849 (2)° | Fragment, colorless |
V = 1018.5 (2) Å3 | 0.60 × 0.30 × 0.25 mm |
Bruker SMART CCD PLATFORM diffractometer | 3530 independent reflections |
Radiation source: fine-focus sealed tube | 3301 reflections with I > 2σ(I) |
Detector resolution: 0 pixels mm-1 | Rint = 0.016 |
ω scans | θmax = 25.0°, θmin = 2.3° |
Absorption correction: multi-scan (SADABS; Bruker, 1999) | h = −8→8 |
Tmin = 0.186, Tmax = 0.264 | k = −9→9 |
7549 measured reflections | l = −21→21 |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.036 | H-atom parameters constrained |
wR(F2) = 0.096 | w = 1/[σ2(Fo2) + (0.0448P)2 + 0.6375P] where P = (Fo2 + 2Fc2)/3 |
S = 1.04 | (Δ/σ)max = 0.003 |
3530 reflections | Δρmax = 0.58 e Å−3 |
271 parameters | Δρmin = −0.62 e Å−3 |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
x | y | z | Uiso*/Ueq | ||
S1 | 0.37024 (8) | 0.03706 (7) | 0.77485 (3) | 0.04724 (16) | |
S2 | 0.28022 (8) | 0.43662 (6) | 0.60143 (3) | 0.04326 (16) | |
S3 | 0.29160 (7) | −0.08482 (6) | 0.60835 (3) | 0.03773 (15) | |
Cl1 | −0.25853 (15) | 0.26317 (14) | 1.03311 (5) | 0.1060 (4) | |
Cl2 | −0.35272 (13) | 0.55565 (14) | 0.87265 (5) | 0.1002 (3) | |
N1 | 0.3383 (3) | 0.1643 (2) | 0.70469 (10) | 0.0446 (4) | |
C11 | −0.0832 (4) | 0.2042 (4) | 0.95977 (15) | 0.0698 (8) | |
O11 | 0.5492 (2) | 0.0699 (3) | 0.79694 (10) | 0.0662 (5) | |
C12 | −0.1312 (4) | 0.1098 (4) | 0.90386 (16) | 0.0744 (8) | |
H12 | −0.255949 | 0.079825 | 0.904470 | 0.089* | |
O12 | 0.3336 (3) | −0.1291 (2) | 0.75832 (9) | 0.0611 (5) | |
C13 | 0.0077 (4) | 0.0596 (4) | 0.84652 (15) | 0.0634 (7) | |
H13 | −0.022673 | −0.004985 | 0.808228 | 0.076* | |
C14 | 0.1913 (3) | 0.1057 (3) | 0.84637 (12) | 0.0486 (5) | |
C15 | 0.2376 (4) | 0.2030 (4) | 0.90258 (15) | 0.0651 (7) | |
H15 | 0.361647 | 0.235004 | 0.901832 | 0.078* | |
C16 | 0.0982 (5) | 0.2520 (4) | 0.95971 (16) | 0.0771 (8) | |
H16 | 0.127549 | 0.317278 | 0.997969 | 0.092* | |
C21 | −0.1739 (4) | 0.5178 (3) | 0.79780 (14) | 0.0581 (6) | |
O21 | 0.2169 (3) | 0.52024 (18) | 0.53771 (9) | 0.0608 (5) | |
C22 | −0.2195 (3) | 0.4463 (3) | 0.73429 (15) | 0.0568 (6) | |
H22 | −0.343084 | 0.416516 | 0.731865 | 0.068* | |
O22 | 0.4612 (2) | 0.4680 (2) | 0.62072 (10) | 0.0604 (5) | |
C23 | −0.0786 (3) | 0.4197 (3) | 0.67448 (13) | 0.0481 (5) | |
H23 | −0.106709 | 0.374468 | 0.630332 | 0.058* | |
C24 | 0.1050 (3) | 0.4603 (2) | 0.68022 (11) | 0.0390 (4) | |
C25 | 0.1500 (3) | 0.5307 (3) | 0.74424 (14) | 0.0527 (6) | |
H25 | 0.274276 | 0.557063 | 0.747588 | 0.063* | |
C26 | 0.0074 (4) | 0.5613 (3) | 0.80321 (14) | 0.0634 (7) | |
H26 | 0.033945 | 0.611211 | 0.846482 | 0.076* | |
C31 | 0.3056 (3) | 0.1145 (2) | 0.63973 (11) | 0.0364 (4) | |
N32 | 0.2750 (2) | 0.23124 (19) | 0.58320 (9) | 0.0380 (4) | |
C33 | 0.2499 (3) | 0.1635 (2) | 0.51252 (11) | 0.0341 (4) | |
C34 | 0.2275 (3) | 0.2439 (3) | 0.44425 (12) | 0.0421 (5) | |
H34 | 0.223853 | 0.358527 | 0.439781 | 0.051* | |
C35 | 0.2108 (3) | 0.1491 (3) | 0.38283 (12) | 0.0444 (5) | |
H35 | 0.194170 | 0.201233 | 0.336651 | 0.053* | |
C36 | 0.2181 (3) | −0.0213 (3) | 0.38840 (12) | 0.0446 (5) | |
H36 | 0.207626 | −0.081849 | 0.346003 | 0.054* | |
C37 | 0.2409 (3) | −0.1021 (3) | 0.45611 (12) | 0.0408 (4) | |
H37 | 0.245905 | −0.216761 | 0.460103 | 0.049* | |
C38 | 0.2561 (3) | −0.0077 (2) | 0.51843 (11) | 0.0344 (4) |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0575 (3) | 0.0479 (3) | 0.0374 (3) | 0.0024 (2) | −0.0118 (2) | −0.0003 (2) |
S2 | 0.0554 (3) | 0.0303 (3) | 0.0419 (3) | −0.0057 (2) | 0.0020 (2) | −0.0013 (2) |
S3 | 0.0444 (3) | 0.0310 (3) | 0.0382 (3) | −0.00082 (19) | −0.0080 (2) | 0.00066 (19) |
Cl1 | 0.1077 (7) | 0.1351 (8) | 0.0629 (5) | 0.0373 (6) | 0.0185 (4) | 0.0011 (5) |
Cl2 | 0.0861 (6) | 0.1271 (8) | 0.0752 (5) | 0.0237 (5) | 0.0257 (4) | −0.0123 (5) |
N1 | 0.0580 (11) | 0.0396 (9) | 0.0371 (9) | −0.0001 (8) | −0.0102 (8) | −0.0020 (7) |
C11 | 0.0794 (19) | 0.0823 (19) | 0.0431 (14) | 0.0196 (15) | 0.0004 (13) | 0.0029 (13) |
O11 | 0.0552 (10) | 0.0930 (14) | 0.0529 (10) | 0.0019 (9) | −0.0177 (8) | −0.0013 (9) |
C12 | 0.0550 (15) | 0.106 (2) | 0.0613 (17) | 0.0027 (15) | −0.0084 (13) | 0.0035 (16) |
O12 | 0.0945 (13) | 0.0420 (9) | 0.0471 (9) | 0.0052 (8) | −0.0141 (9) | 0.0016 (7) |
C13 | 0.0618 (16) | 0.0836 (19) | 0.0475 (13) | −0.0034 (13) | −0.0154 (12) | −0.0072 (12) |
C14 | 0.0582 (13) | 0.0509 (13) | 0.0373 (11) | −0.0007 (10) | −0.0100 (10) | 0.0009 (9) |
C15 | 0.0734 (17) | 0.0726 (17) | 0.0507 (14) | −0.0130 (14) | −0.0076 (12) | −0.0140 (12) |
C16 | 0.097 (2) | 0.084 (2) | 0.0501 (15) | −0.0054 (17) | −0.0037 (15) | −0.0209 (14) |
C21 | 0.0602 (15) | 0.0570 (14) | 0.0524 (14) | 0.0115 (11) | 0.0045 (11) | −0.0013 (11) |
O21 | 0.1006 (14) | 0.0339 (8) | 0.0444 (9) | 0.0050 (8) | −0.0013 (8) | 0.0044 (7) |
C22 | 0.0466 (13) | 0.0589 (14) | 0.0638 (15) | 0.0001 (11) | −0.0053 (11) | 0.0003 (12) |
O22 | 0.0537 (10) | 0.0565 (10) | 0.0687 (11) | −0.0206 (8) | 0.0060 (8) | −0.0099 (8) |
C23 | 0.0537 (13) | 0.0443 (12) | 0.0478 (12) | −0.0029 (10) | −0.0115 (10) | −0.0051 (9) |
C24 | 0.0473 (11) | 0.0286 (9) | 0.0405 (11) | −0.0001 (8) | −0.0041 (9) | −0.0028 (8) |
C25 | 0.0536 (13) | 0.0529 (13) | 0.0537 (13) | −0.0041 (10) | −0.0096 (10) | −0.0158 (11) |
C26 | 0.0749 (18) | 0.0683 (16) | 0.0480 (14) | 0.0060 (13) | −0.0088 (12) | −0.0228 (12) |
C31 | 0.0372 (10) | 0.0342 (10) | 0.0371 (10) | 0.0003 (8) | −0.0032 (8) | 0.0004 (8) |
N32 | 0.0482 (9) | 0.0302 (8) | 0.0349 (8) | 0.0010 (7) | −0.0039 (7) | −0.0014 (6) |
C33 | 0.0310 (9) | 0.0351 (10) | 0.0352 (10) | 0.0003 (7) | −0.0014 (7) | −0.0028 (8) |
C34 | 0.0455 (11) | 0.0394 (11) | 0.0405 (11) | 0.0004 (9) | −0.0046 (9) | 0.0032 (9) |
C35 | 0.0461 (11) | 0.0517 (12) | 0.0360 (11) | −0.0025 (9) | −0.0092 (9) | 0.0039 (9) |
C36 | 0.0457 (11) | 0.0500 (12) | 0.0393 (11) | −0.0057 (9) | −0.0077 (9) | −0.0063 (9) |
C37 | 0.0420 (11) | 0.0370 (10) | 0.0441 (11) | −0.0045 (8) | −0.0067 (9) | −0.0049 (9) |
C38 | 0.0303 (9) | 0.0357 (10) | 0.0367 (10) | −0.0017 (7) | −0.0033 (7) | 0.0008 (8) |
S1—O11 | 1.4252 (18) | C21—C26 | 1.370 (4) |
S1—O12 | 1.4331 (18) | C21—C22 | 1.375 (4) |
S1—N1 | 1.6244 (18) | C22—C23 | 1.374 (3) |
S1—C14 | 1.761 (2) | C22—H22 | 0.9300 |
S2—O22 | 1.4165 (18) | C23—C24 | 1.381 (3) |
S2—O21 | 1.4186 (17) | C23—H23 | 0.9300 |
S2—N32 | 1.7133 (16) | C24—C25 | 1.377 (3) |
S2—C24 | 1.752 (2) | C25—C26 | 1.377 (3) |
S3—C31 | 1.743 (2) | C25—H25 | 0.9300 |
S3—C38 | 1.7439 (19) | C26—H26 | 0.9300 |
Cl1—C11 | 1.743 (3) | C31—N32 | 1.389 (3) |
Cl2—C21 | 1.737 (2) | N32—C33 | 1.429 (2) |
N1—C31 | 1.294 (3) | C33—C34 | 1.383 (3) |
C11—C16 | 1.365 (4) | C33—C38 | 1.389 (3) |
C11—C12 | 1.368 (4) | C34—C35 | 1.383 (3) |
C12—C13 | 1.380 (4) | C34—H34 | 0.9300 |
C12—H12 | 0.9300 | C35—C36 | 1.382 (3) |
C13—C14 | 1.375 (3) | C35—H35 | 0.9300 |
C13—H13 | 0.9300 | C36—C37 | 1.376 (3) |
C14—C15 | 1.381 (3) | C36—H36 | 0.9300 |
C15—C16 | 1.377 (4) | C37—C38 | 1.391 (3) |
C15—H15 | 0.9300 | C37—H37 | 0.9300 |
C16—H16 | 0.9300 | ||
O11—S1—O12 | 118.29 (12) | C21—C22—H22 | 120.7 |
O11—S1—N1 | 107.50 (11) | C22—C23—C24 | 119.7 (2) |
O12—S1—N1 | 111.51 (9) | C22—C23—H23 | 120.2 |
O11—S1—C14 | 108.24 (11) | C24—C23—H23 | 120.2 |
O12—S1—C14 | 108.49 (11) | C25—C24—C23 | 121.4 (2) |
N1—S1—C14 | 101.45 (10) | C25—C24—S2 | 119.38 (17) |
O22—S2—O21 | 119.94 (11) | C23—C24—S2 | 119.02 (16) |
O22—S2—N32 | 108.05 (10) | C26—C25—C24 | 118.7 (2) |
O21—S2—N32 | 104.94 (9) | C26—C25—H25 | 120.7 |
O22—S2—C24 | 110.58 (10) | C24—C25—H25 | 120.7 |
O21—S2—C24 | 108.54 (10) | C21—C26—C25 | 119.7 (2) |
N32—S2—C24 | 103.39 (9) | C21—C26—H26 | 120.2 |
C31—S3—C38 | 90.95 (9) | C25—C26—H26 | 120.2 |
C31—N1—S1 | 122.39 (15) | N1—C31—N32 | 118.90 (18) |
C16—C11—C12 | 121.6 (3) | N1—C31—S3 | 130.18 (16) |
C16—C11—Cl1 | 119.4 (2) | N32—C31—S3 | 110.92 (14) |
C12—C11—Cl1 | 118.9 (3) | C31—N32—C33 | 114.44 (16) |
C11—C12—C13 | 119.2 (3) | C31—N32—S2 | 119.26 (13) |
C11—C12—H12 | 120.4 | C33—N32—S2 | 126.24 (13) |
C13—C12—H12 | 120.4 | C34—C33—C38 | 120.44 (18) |
C14—C13—C12 | 119.6 (3) | C34—C33—N32 | 129.24 (18) |
C14—C13—H13 | 120.2 | C38—C33—N32 | 110.29 (16) |
C12—C13—H13 | 120.2 | C35—C34—C33 | 118.10 (19) |
C13—C14—C15 | 120.7 (2) | C35—C34—H34 | 120.9 |
C13—C14—S1 | 119.75 (18) | C33—C34—H34 | 120.9 |
C15—C14—S1 | 119.6 (2) | C36—C35—C34 | 121.6 (2) |
C16—C15—C14 | 119.4 (3) | C36—C35—H35 | 119.2 |
C16—C15—H15 | 120.3 | C34—C35—H35 | 119.2 |
C14—C15—H15 | 120.3 | C37—C36—C35 | 120.63 (19) |
C11—C16—C15 | 119.5 (3) | C37—C36—H36 | 119.7 |
C11—C16—H16 | 120.2 | C35—C36—H36 | 119.7 |
C15—C16—H16 | 120.2 | C36—C37—C38 | 118.20 (19) |
C26—C21—C22 | 121.9 (2) | C36—C37—H37 | 120.9 |
C26—C21—Cl2 | 119.4 (2) | C38—C37—H37 | 120.9 |
C22—C21—Cl2 | 118.7 (2) | C33—C38—C37 | 121.04 (18) |
C23—C22—C21 | 118.6 (2) | C33—C38—S3 | 113.31 (14) |
C23—C22—H22 | 120.7 | C37—C38—S3 | 125.62 (15) |
D—H···A | D—H | H···A | D···A | D—H···A |
C12—H12···O11i | 0.93 | 2.53 | 3.203 (3) | 130 |
C22—H22···O22i | 0.93 | 2.59 | 3.249 (3) | 128 |
C37—H37···O21ii | 0.93 | 2.50 | 3.339 (3) | 151 |
C34—H34···O21 | 0.93 | 2.22 | 2.837 (3) | 123 |
Symmetry codes: (i) x−1, y, z; (ii) x, y−1, z. |
Funding information
Funding for this research was provided by: NIH (award No. 1R15AI113653-01 to TJH).
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