Influence of oligomeric herbicidal ionic liquids with MCPA and Dicamba anions on the community structure of autochthonic bacteria present in agricultural soil

Ławniczak, Łukasz; Syguda, Anna; Borkowski, Andrzej; Cyplik, Paweł; Marcinkowska, Katarzyna; Wolko, Łukasz; Praczyk, T.; Chrzanowski, Łukasz; Pernak, Juliusz

doi:10.1016/j.scitotenv.2016.04.109

Cited by 51 publications

(35 citation statements)

References 41 publications

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“…Due to greasy nature of [RDGN][dicamba] ( 1 c – 7 c ) we were unable to acquire the exact values of their viscosities using a Rheotec RC30‐CPS, however, we were able to establish that they all exceed the value of 200 Pa s. With regard to this data, DSHILs 2 d – 7 d exhibited a deviation from the predicted linear average of the two parent HILs and should be characterized by substantially higher viscosities. Such divergence might be related to the above‐mentioned influence of the dicamba anion, which is capable of forming strong hydrogen bonds, which were found to be hindered in a double‐salt system. The second group includes two DSHILs with the longest alkyl chains ( 6 d and 7 d ), that surprisingly possessed smaller viscosities than the corresponding MCPA analogues ( 6 b and 7 b ) as well as the dicamba salts ( 6 c and 7 c ).…”

Section: Resultsmentioning

confidence: 66%

“…The latter strategy led to development of novel bifunctional ILs, capable of preserving both types of biological properties. Because the prolonged use of a single anti‐weed agent usually results in a rapid enhancement of the plant's herbicidal resistance, a concept of utilizing multiple herbicides (in oligomeric forms) has been recently adopted for HILs …”

Section: Introductionmentioning

confidence: 99%

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Synthesis and Structure–Property Relationships in Herbicidal Ionic Liquids and their Double Salts

et al. 2018

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In this study, two homologous series of novel herbicidal ionic liquids (HILs) were synthesized in a simple metathesis reaction between alkyl[2‐(2‐hydroxyethoxy)ethyl]dimethylammonium bromides and alkali metal salts of 4‐chloro‐2‐methylphenoxyacetic acid (MCPA) or 3,6‐dichloro‐2‐methoxybenzoic acid (dicamba), known as popular herbicides from the class of growth regulators. These HILs were subsequently mixed to prepare double‐salt herbicidal ionic liquids (DSHILs). The DSHILs were characterized by substantially altered parameters of viscosity, refractive index, glass transition temperatures and surface activity compared to the average values expected for ideal mixtures of their individual components (HILs). Interestingly, DSHILs possessed superior physicochemical properties such as relatively low viscosity or facilitated formation of micelles, which emphasizes the complex nature of multi‐ion interactions in the microstructures of ionic liquid mixtures. The biological tests showed improved efficiency of DSHILs against tested weeds compared to the reference herbicides and parent HILs.

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Section: Resultsmentioning

confidence: 66%

Section: Introductionmentioning

confidence: 99%

Synthesis and Structure–Property Relationships in Herbicidal Ionic Liquids and their Double Salts

et al. 2018

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“…It should also be noted that the test was carried out with the use of activated sludge microorganisms and that the biodegradability of the studied compounds in agricultural soils may differ . Furthermore, fully synthetic ILs may notably decrease the biodiversity of microbial populations on the example of phosphonium‐based ILs or ammonium‐based ILs, whereas HILs did not significantly impact the overall biodiversity or did not exhibit mutagenic properties . Acetylcholine is well known to not penetrate through lipid membranes, however it usually binds with ion channels present in the cell membrane.…”

Section: Resultsmentioning

confidence: 99%

Herbicidal Ionic Liquids Containing the Acetylcholine Cation

et al. 2019

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This study presents a new group of herbicidal ionic liquids (HILs) based on a cation occurs commonly in nature−acetylcholine. The HILs were obtained with a high yield through ion exchange between acetylcholine chloride and potassium or sodium salts of selected acids with herbicidal activity. The results of the herbicidal activity measurement against common oilseed rape (Brassica napus L.) exceeded those of the commercial products. Spray solutions of the synthesized HILs revealed high surface activity and wetting properties which further manifested as higher herbicidal activity. The reduction of surface tension and low contact angles together with the specific action of acetylcholine allowed for better penetration of synthesized HILs into plant tissues. In addition, OECD 301F tests confirmed high mineralization of the HILs. The simple transformation of commercial herbicides into acetylcholine HILs proved to be a very effective method of increasing their activity, and constitutes an interesting solution to the problem of weed infestation with the use of a substance commonly found in nature.

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“…Bacterial communities are known to reflect their microenvironmental conditions by readily responding at extremely fast rates to environmental and pollution changes (Bell et al, 2009;Thiyagarajan et al, 2010;Ławniczak et al, 2016;Sydow et al, 2016). However, human activities have dramatically changed the composition and organisation of soils.…”

Section: Introductionmentioning

confidence: 99%

The Heavy-Metal Resistance Determinant of Newly Isolated Bacterium from a Nickel-Contaminated Soil in Southwest Slovakia

Remenár

Kamlárová

Harichová

et al. 2018

Polish Journal of Microbiology

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A bacterial isolate MR-CH-I2 [KC809939] isolated from soil contaminated mainly by high nickel concentrations in southwest Slovakia was previously found carrying nccA-like heavy-metal resistance determinant, marked as MR-CH-I2-HMR [KF218096]. According to phylogenetic analysis of short (696 bp) 16S rDNA (16S rRNA) sequences this bacterium was tentatively assigned to Uncultured beta proteobacterium clone GC0AA7ZA05PP1 [JQ913301]. nccA-like gene product was on the same base of its partial (581 bp) sequences tentatively assigned to CzcA family heavy metal efflux pump [YP_001899332] from Ralstonia picketii 12J with 99% similarity. In this study the bacterium MR-CH-I2 and its heavy-metal resistance determinant were more precisely identified. This bacterial isolate was on the base of phylogenetic analysis of almost the whole (1,500 bp) 16S rDNA (16S rRNA) sequence, MR-CH-I2 [MF102046], and sequence for gyrB gene and its product respectively, MR-CH-I2-gyrB [MF134666], assigned to R. picketii 12J [CP001068] with 99 and 100% similarities, respectively. In addition, the whole nccA-like heavy-metal resistance gene sequence (3,192 bp), marked as MR-CH-I2-nccA [KR476581], was obtained and on the base of phylogenetic analysis its assignment was confirmed to MULTISPECIES: cation efflux system protein CzcA [WP_004635342] from Burkholderiaceae with 98% similarity. Furthermore, although the bacterium carried one high molecular plasmid of about 50 kb in size, nccA-like gene was not located on this plasmid. Finally, the results from RT-PCR analysis showed that MR-CH-I2-nccA gene was significantly induced only by the addition of nickel.

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Influence of oligomeric herbicidal ionic liquids with MCPA and Dicamba anions on the community structure of autochthonic bacteria present in agricultural soil

Cited by 51 publications

References 41 publications

Synthesis and Structure–Property Relationships in Herbicidal Ionic Liquids and their Double Salts

Synthesis and Structure–Property Relationships in Herbicidal Ionic Liquids and their Double Salts

Herbicidal Ionic Liquids Containing the Acetylcholine Cation

The Heavy-Metal Resistance Determinant of Newly Isolated Bacterium from a Nickel-Contaminated Soil in Southwest Slovakia

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