Colchicine, Caffeine, Gramine, and Their Derivatives as Potential Herbicides, Fungicides, and Insecticides
Abstract
:1. Introduction
2. Results and Discussion
3. Materials and Methods
3.1. Compound Preparation
3.2. In Silico Screening/Calculations
3.3. Fungicidal Tests
3.3.1. Activity against Phytophthora Infestans in the Microtiter Plate Assay
3.3.2. Microtiter Plate Activity against Zymoseptoria Tritici
3.3.3. Microtiter Plate Activity against Botrytis Cinerea
3.3.4. Activity against Fusarium Culmorum in the Microtiter Plate Test
3.4. Insecticidal Tests
3.4.1. Test to Evaluate the Control of Vetch Aphid (Megoura viciae) by Contact or Systemic Means
3.4.2. Test to Evaluate the Control of Caenorhabditis elegans by Contact or Systemic Means
3.4.3. Test to Evaluate the Control of Green Peach Aphid (Myzus persicae) by Systemic Means
3.4.4. Boll Weevil (Anthonomus grandis) Control Test
3.4.5. Test to Evaluate the Control of Mediterranean Fruit Fly (Ceratitis capitata)
3.4.6. Test to Evaluate the Control of Tobacco Budworm (Heliothis virescens)
3.4.7. Test to Evaluate the Control of Tobacco Budworm Yellow Fever Mosquito (Aedes aegypti) Control Assay
3.4.8. Test to Evaluate Control of Greenhouse Whitefly (Trialeurodes vaporariorum)
3.5. Herbicidal Test
4. Conclusions
Author Contributions
Funding
Data Availability Statement
Acknowledgments
Conflicts of Interest
References
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No. | R | R1 | Ref. | |
1 | -OCH3 colchicine | -COCH3 | - | |
2 | -OH colchiceine | -COCH3 | [35] | |
3 | -SCH3 | -COCH3 | [36] | |
4 | -SCH2CH3 | -COCH3 | [36] | |
5 | -SCH2CH2CH3 | -COCH3 | [36] | |
6 | -SCH(CH3)2 | -COCH3 | [36] | |
7 | -SCH2CH2CH2CH3 | -COCH3 | [36] | |
8 | -SCH3 | -H | [37] | |
9 | -SCH2CH3 | -H | [37] | |
10 | -SCH2CH2CH3 | -H | [37] | |
11 | -SCH(CH3)2 | -H | [37] | |
12 | -SCH2CH2CH2CH3 | -H | [37] |
Compounds | No. | R1 | R2 | Ref. |
---|---|---|---|---|
13 | -N(CH3)2 gramine | -H | ||
14 | -OCOCH3 | -COCH3 | [47] | |
15 | -OC CH | -H | [47] | |
16 | -OCH2CH3 | -(CH2)3Br | [47] | |
17 | -OCH2CH3 | -(CH2)3N3 | [47] | |
18 | -OCH2CH3 | -(CH2)5Br | [47] | |
19 | -OCH2CH3 | -(CH2)5N3 | [47] | |
20 | -H | [47] | ||
21 | -H | [47] | ||
22 | -H | [47] | ||
23 | -H | [47] | ||
24 | -OC2H5 | [47] | ||
25 | -OC2H5 | [47] | ||
26 | -OH | -COCH3 | [48] | |
27 | -OC2H5 | -H | [49] | |
28 | -OCH2CH2CH3 | -H | [49] | |
29 | -OCH2CH2CH2CH3 | -H | [49] | |
30 | -OCH2CH2CH2CH2CH3 | -H | [49] | |
31 | -OCH(CH3)2 | -H | [49] | |
32 | -OCH2CH2CH(CH3)2 | -H | [49] | |
33 | -H | [49] | ||
34 | -H | [49] | ||
35 | -H | [49] |
Caffeine 36 | No. | R1 | Ref. |
36 | -H | - | |
37 | -Br | [50] | |
38 | -N3 | [51] | |
39 | -SCH3 | [50] | |
40 | -SC2H5 | [50] | |
41 | -SCH2CH2CH3 | [50] | |
42 | -SCH(CH3)2 | [50] | |
43 | -SC(CH3)3 | [50] | |
44 | [50] | ||
45 | -NHNH2 | [52] | |
46 | -NH(CH2)2NH2 | [48] | |
47 | [53] | ||
48 | [53] |
Comp. No. | Fungi Stains | |||
---|---|---|---|---|
Botrytis cinerea | Fusarium culmorum | Phytophthora infestans | Zymoseptoria tritici | |
13 | 3 | 3 | 3 | 3 |
14 | 3 | 3 | 2 | 2 |
15 | 3 | 3 | 3 | 3 |
17 | 3 | 3 | 3 | 3 |
26 | 3 | 3 | 3 | 3 |
27 | 2 | 3 | 3 | 3 |
28 | 3 | 3 | 3 | 3 |
29 | 1 | 2 | 3 | 1 |
30 | 3 | 3 | 3 | 3 |
31 | 2 | 3 | 3 | 2 |
32 | 3 | 3 | 3 | 3 |
33 | 3 | 3 | 3 | 3 |
34 | 3 | 3 | 3 | 3 |
35 | 1 | 1 | 2 | 1 |
Comp. | Water Solubility | ||
---|---|---|---|
LogS (ESOL) [54] /Class | Log S (Ali) [55] /Class | Log S (SILICOS-IT) [56] /Class | |
13 | −2.42/soluble | −1.80/very soluble | −3.79/soluble |
14 | −2.39/soluble | −2.19/soluble | −3.28/soluble |
15 | −2.69/soluble | −2.39/soluble | −3.51/soluble |
17 | −3.35/soluble | −4.22/moderate soluble | −4.76/moderate soluble |
26 | −1.99/very soluble | −1.48/very soluble | −2.63/soluble |
27 | −2.48/soluble | −2.11/soluble | −4.22/moderate soluble |
28 | −2.79/soluble | −2.66/soluble | −4.63/moderate soluble |
29 | −3.01/soluble | −3.03/soluble | −5.04 moderate soluble |
30 | −3.34/soluble | −3.59/soluble | −5.44/moderate soluble |
31 | −2.80/soluble | −2.57/soluble | −4.25 moderate soluble |
32 | −3.35/soluble | −3.49/soluble | −5.07/moderate soluble |
33 | −3.54/soluble | −3.28/soluble | −5.87/moderate soluble |
34 | −2.65/soluble | −1.95/very soluble | −4.22/moderate soluble |
35 | −3.73/soluble | −4.56/moderate soluble | −4.39/moderate soluble |
Comp. | Lipophilicity | |||||||
---|---|---|---|---|---|---|---|---|
LogP [57] | LogP (iLOGP) [58] | LogP (XLOGP3) [59] | LogP (WLOGP) [60,61,62] | LogP (MLOGP) [63] | LogP (SILICOS-IT) [64] | Consensus LogP [65] | Log P [66] | |
13 | 1.89 | 1.88 | 1.78 | 2.08 | 1.55 | 2.41 | 1.94 | 2.23 |
14 | 2.45 | 2.43 | 1.57 | 2.21 | 1.84 | 2.06 | 2.02 | 2.36 |
15 | 1.82 | 2.03 | 2.23 | 2.20 | 1.47 | 3.00 | 2.19 | 2.28 |
17 | 3.46 | 3.02 | 3.21 | 3.73 | 1.27 | 1.98 | 2.64 | 3.33 |
26 | 1.75 | 1.77 | 1.00 | 1.64 | 1.40 | 1.64 | 1.49 | 1.79 |
27 | 2.42 | 2.01 | 1.96 | 2.55 | 1.55 | 3.18 | 2.25 | 2.7 |
28 | 2.92 | 2.26 | 2.49 | 2.94 | 1.84 | 3.53 | 2.61 | 3.09 |
29 | 3.48 | 2.58 | 2.85 | 3.33 | 2.11 | 3.89 | 2.95 | 3.48 |
30 | 3.98 | 2.85 | 3.39 | 3.72 | 2.37 | 4.26 | 3.32 | 3.87 |
31 | 2.78 | 2.29 | 2.40 | 2.94 | 1.84 | 3.35 | 2.56 | 3.09 |
32 | 3.69 | 2.67 | 3.29 | 3.58 | 2.37 | 4.09 | 3.20 | 3.73 |
33 | 3.48 | 2.05 | 2.52 | 2.43 | 2.75 | 3.41 | 2.63 | 2.90 |
34 | 1.95 | 1.48 | 1.63 | 2.41 | 1.16 | 2.42 | 1.82 | 2.41 |
35 | 3.42 | 2.61 | 3.28 | 3.25 | 2.29 | 4.63 | 3.21 | 3.72 |
Compounds Structures | Dotted Models | Space-Filling CPK Models |
---|---|---|
Gramine 13 | ||
14 | ||
15 | ||
17 | ||
26 | ||
27 | ||
28 | ||
29 | ||
30 | ||
31 | ||
32 | ||
33 | ||
34 | ||
35 |
Comp. | Molecular Weight | Number of Hydrogen Bond Acceptors | Number of Hydrogen Bond Donors | Number of Atoms | Number of Bonds | Number of Rotable Bonds | Molecular Refractivity | Topological Polar Surface Area | Predicted LD50 mg/kg | Precicted Toxicity Active 1–6 Inactive |
---|---|---|---|---|---|---|---|---|---|---|
13 | 174.24 | 15 | 1 | 27 | 28 | 2 | 56.77 | 19.03 | 380 | 4 |
14 | 231.25 | 16 | 0 | 30 | 31 | 4 | 64.29 | 48.3 | 500 | 4 |
15 | 171.2 | 10 | 1 | 22 | 23 | 2 | 52.13 | 25.02 | 1420 | 4 |
17 | 258.32 | 20 | 0 | 37 | 38 | 7 | 73.3 | 63.91 | 500 | 4 |
26 | 189.21 | 13 | 1 | 25 | 26 | 2 | 54.56 | 42.23 | 500 | 4 |
27 | 175.23 | 14 | 1 | 26 | 27 | 3 | 53.93 | 25.02 | 1425 | 4 |
28 | 189.25 | 16 | 1 | 29 | 30 | 4 | 58.77 | 25.0 | 5000 | 5 |
29 | 203.28 | 18 | 1 | 32 | 33 | 5 | 63.58 | 25.02 | 1000 | 4 |
30 | 217.31 | 20 | 1 | 35 | 36 | 6 | 68.38 | 25.02 | 1000 | 4 |
31 | 189.25 | 16 | 1 | 29 | 30 | 3 | 58.77 | 25.02 | 1425 | 4 |
32 | 217.31 | 20 | 1 | 35 | 36 | 5 | 68.38 | 25.02 | 1000 | 4 |
33 | 276.29 | 15 | 1 | 33 | 36 | 2 | 83.06 | 53.17 | 2000 | 4 |
34 | 197.24 | 12 | 1 | 26 | 28 | 2 | 59.83 | 33.61 | 1000 | 4 |
35 | 276.42 | 19 | 1 | 34 | 36 | 4 | 87.38 | 76.42 | 5600 | 6 |
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Kurek, J.; Sierakowska, A.; Berdzik, N.; Jasiewicz, B. Colchicine, Caffeine, Gramine, and Their Derivatives as Potential Herbicides, Fungicides, and Insecticides. Int. J. Mol. Sci. 2024, 25, 10081. https://doi.org/10.3390/ijms251810081
Kurek J, Sierakowska A, Berdzik N, Jasiewicz B. Colchicine, Caffeine, Gramine, and Their Derivatives as Potential Herbicides, Fungicides, and Insecticides. International Journal of Molecular Sciences. 2024; 25(18):10081. https://doi.org/10.3390/ijms251810081
Chicago/Turabian StyleKurek, Joanna, Arleta Sierakowska, Natalia Berdzik, and Beata Jasiewicz. 2024. "Colchicine, Caffeine, Gramine, and Their Derivatives as Potential Herbicides, Fungicides, and Insecticides" International Journal of Molecular Sciences 25, no. 18: 10081. https://doi.org/10.3390/ijms251810081