Sulfonamide modified chitosan oligosaccharide with high nematicidal activity against Meloidogyne incognita.

Chitosan oligosaccharide (COS) modification is a feasible way to develop novel green nematicides. This study involved the synthesis of various COS sulfonamide derivatives via hydroxylated protection and deprotection, which were then characterized using NMR, FTIR, MS, elemental analysis, XRD, and TG/DTG. In vitro experiments found that COS-alkyl sulfonamide derivatives (S6 and S11-S13) exhibited high mortality (>98 % at 1 mg/mL) against Meloidogyne incognita second-instar larvaes (J2s) among the derivatives. S6 can cause vacuole-like structures in the middle and tail regions of the nematode body and effectively inhibit egg hatching. In vivo tests have found that S6 has well control effects and low plant toxicity. Additionally, the structure-activity studies revealed that S6 with a high degree of substitution, a low molecular weight, and a sulfonyl bond on the amino group of the COS backbone exhibited increased nematicidal activity. The sulfonamide group is a potential active group for developing COS-based nematicides.

Activity of chitin/chitosan/chitosan oligosaccharide against plant pathogenic nematodes and potential modes of application in agriculture: A review.

Chemical nematicide is the most common method of controlling plant-parasitic nematodes (PPN). Given the negative impact of chemical nematicides on the environment and ecosystem, it is necessary to seek their alternatives and novel modes of application. Chitin oligo/polysaccharide (COPS), including chitosan and chitosan oligosaccharide, has unique biological properties. By producing ammonia, encouraging the growth of antagonistic bacteria, and enhancing crop tolerance, COPSs help suppress PPN growth during soil remediation. COPS is also an effective sustained-release carrier that can be used to overcome the shortcomings of nematicidal substances. This review summarizes the advancements of COPS research in nematode control from three perspectives of action mechanism as well as in slow-release carrier-loaded nematicides. Further, it discusses potential agricultural applications for nematode disease management.

Novel Lead Compound Discovery from Aspergillus fumigatus 1T-2 against Meloidogyne incognita Based on a Chemical Ecology Study.

To replace biohazardous nematicides, there is an ever-increasing need to identify natural product-based agents to contain root-knot nematodes (RKNs) in agriculture. In this chemical ecology study, an antagonistic fungus Aspergillus fumigatus 1T-2, which could cause the formation of withering of the gut and vacuole-like structures in the nematode body, was isolated based on the gradually increased antagonistic interactions between the soil fungi and RKNs. Based on these typical morphological characteristics, a potent nematode-antagonistic compound 2-furoic acid, which had a simple structure, was successfully identified from 1T-2 fermentation broth by liquid chromatography-mass spectrometry (LC-MS). 2-Furoic acid showed effective mortality activity in vitro, of which the LC50 value to Megalaima incognita at 24 h was 37.75 µg/mL. 2-Furoic acid had similar mortality activity to the positive control fosthiazate at 30 µg/mL. Continuous 2-furoic acid exposure had obvious negative influences on both nematode vitality and egg hatchability. Notably, significant variations were observed in nematodes and eggs with 2-furoic acid treatment, which might be induced by novel nematocidal mechanisms. Furthermore, the 1T-2 fermentation broth and 2-furoic acid had significant control efficacy on M. incognita under the greenhouse test-tube assay. Overall, these findings provide valuable insights into the use of 2-furoic acid with biocontrol potential as a preferable lead structure for the development of innovative nematicides.

Fluoroalkenyl-Grafted Chitosan Oligosaccharide Derivative: An Exploration for Control Nematode Meloidogyne Incognita.

The exploration of novel, environmentally friendly, and efficient nematicides is essential, and modifying natural biomacromolecules is one feasible approach. In this study, 6-O-(trifluorobutenyl-oxadiazol)-chitosan oligosaccharide derivative was synthesized and characterized by FTIR, NMR, and TG/DTG. Its bioactivity and action mode against root-knot nematode M. incognita were estimated. The results show that the derivative shows high nematicidal activity against J2s, and egg hatching inhibitory activity at 1 mg/mL. The derivative may affect nematode ROS metabolism and further damage intestinal tissue to kill nematode. Meanwhile, by synergism with improving crop resistance, the derivative performed a high control effect on the nematode with low phytotoxicity. These findings suggested that chitosan oligosaccharide derivatives bearing fluoroalkenyl groups are promising green nematicides.

Efficacy of a Chitin-Based Water-Soluble Derivative in Inducing Purpureocillium lilacinum against Nematode Disease (Meloidogyne incognita).

Plant-parasitic nematodes cause severe economic losses annually which has been a persistent problem worldwide. As current nematicides are highly toxic, prone to drug resistance, and have poor stability, there is an urgent need to develop safe, efficient, and green strategies. Natural active polysaccharides such as chitin and chitosan with good biocompatibility and biodegradability and inducing plant disease resistance have attracted much attention, but their application is limited due to their poor solubility. Here, we prepared 6-oxychitin with good water solubility by introducing carboxylic acid groups based on retaining the original skeleton of chitin and evaluated its potential for nematode control. The results showed that 6-oxychitin is a better promoter of the nematicidal potential of Purpureocillium lilacinum than other water-soluble chitin derivatives. After treatment, the movement of J2s and egg hatching were obviously inhibited. Further plant experiments found that it can destroy the accumulation and invasion of nematodes, and has a growth-promoting effect. Therefore, 6-oxychitin has great application potential in the nematode control area.

Characterization of Different Salt Forms of Chitooligosaccharides and Their Effects on Nitric Oxide Secretion by Macrophages.

In this paper, chitooligosaccharides in different salt forms, such as chitooligosaccharide lactate, citrate, adipate, etc., were prepared by the microwave method. They were characterized by SEM, FTIR, NMR, etc., and the nitric oxide (NO) expression was determined in RAW 264.7 cells. The results showed that pure chitooligosaccharide was an irregular spherical shape with rough surface, and its different salt type products are amorphous solid with different honeycomb sizes. In addition to the characteristic absorption peaks of chitooligosaccharides, in FTIR, the characteristic absorption of carboxyl group, methylene group, and aromatic group in corresponding acid appeared. The characteristic absorption peaks of carbon in carboxyl group, hydrogen and carbon in methyl, methylene group, and aromatic group in corresponding acid also appeared in NMR. Therefore, the sugar ring structure and linking mode of chitooligosaccharides did not change after salt formation of chitooligosaccharides. Different salt chitooligosaccharides are completely different in promoting NO secretion by macrophages, and pure chitooligosaccharides are the best.

Chitosan Oligosaccharide Fluorinated Derivative Control Root-Knot Nematode (Meloidogyne incognita) Disease Based on the Multi-Efficacy Strategy.

Plant root-knot nematode disease is a great agricultural problem and commercially available nematicides have the disadvantages of high toxicity and limited usage; thus, it is urgent to develop new nematicides derived from nature substances. In this study, a novel fluorinated derivative was synthesized by modifying chitosan oligosaccharide (COS) using the strategy of multiple functions. The derivatives were characterized by FTIR, NMR, elemental analysis, and TG/DTG. The activity assays show that the derivatives can effectively kill the second instar larvae of Meloidogyne incognita in vitro, among them, chitosan-thiadiazole-trifluorobutene (COSSZFB) perform high eggs hatching inhibitory activity. The derivatives can regulate plant growth (photosynthetic pigment), improve immunity (chitinase and ß-1,3-glucanase), and show low cytotoxicity and phytotoxicity. According to the multi-functional activity, the derivatives exhibit a good control effect on plant root-knot nematode disease in vivo. The results demonstrate that the COS derivatives (especially fluorinated derivative) perform multiple activities and show the potential to be further evaluated as nematicides.

The bioactivity of new chitin oligosaccharide dithiocarbamate derivatives evaluated against nematode disease (Meloidogyne incognita).

Plant-parasitic nematodes cause substantial crop losses annually; however, current nematicides are environmentally unfriendly and highly toxic to nontarget organisms. The development of green efficient nematicides from multifunctional natural bioactive substances such as chitin oligosaccharide (COS) is promising. In this paper, COS dithiocarbamate derivatives (COSDTC, COSDTA, COSDTB) were synthesized to increase nematicidal activity (against Meloidogyne incognita), and their structures were characterized by FTIR, NMR, TGA/DTG and elemental analysis. Furthermore, the nematicidal activities, egg hatching inhibitory activities, plant growth adjustment abilities, cytotoxicity and phytotoxicity of the derivatives were evaluated. The primary mechanism was assessed by heavy metal ion absorption and GSH-binding assays. The results showed COS dithiocarbamate derivatives could possess multiple efficacies, including high nematicidal activities and egg hatching inhibitory activities, plant growth regulating effects, low cell toxicities and phytotoxicities. Additionally, it was inferred that nematicidal activity may be correlated with GSH-binding activity but not heavy metal ion complexation. COS modification has immense potential for controlling plant-parasitic nematodes.

Synthesis, characterization, and antifungal evaluation of diethoxyphosphoryl polyaminoethyl chitosan derivatives.

Botrytis cinerea, Phytophthora capsici Leonian, and Fusarium solani are important plant pathogenic fungi which can cause great crop losses worldwide, but their control methods are limited. It is necessary to develop efficient and green fungicides from abundant marine resources. Chitosan is a non-toxic, biodegradable, biocompatible marine polysaccharide which has prospective applications in agriculture. In this paper, to increase the antifungal activity of chitosan for application, novel water-soluble functional chitosan derivatives were synthesized by grafting polyaminoethyl and diethoxyphosphoryl groups in accordance with a strategy of improving protonation potential. The derivatives were characterized by FTIR, NMR, XRD, SEM, Gaussian 09 and elemental analysis. The antifungal activities against the three fungi and the cytotoxicity were estimated in vitro. The results showed that the derivatives had better antifungal activities and water solubility than chitosan, and had good biocompatibility. They confirmed that these chitosan derivatives can be developed as antifungal agents for plant protection purposes.