The effect of microorganisms on phytotoxicity of herbicides. II. Increase of phytotoxicity of Venzar in the presence of phenolic compounds by Pseudomonas sp. 22.
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[Selective phytotoxic activity of N,N-di,sec.butylamides of aminobenzoic acids mono-, di- and tri-substituted on the nucleus].
N,N-di,sec.butylaminobenzamides, mono-, di- or trisubstituted on the nucleus with methyl and/or halogen groups were prepared and tested for phytotoxicity. The corresponding benzoic acids and series of N-alkyl- and N,N-dialkylamides of 2-amino-3-bromo-5-methyl-, 2-amino-3,5-dibromo, 2-amino-3,5-dichloro- and 3-amino-2,5-dichlorobenzoic acids were studied in parallel. Both pre- and post-emergence phytotoxicity tests were carried out with doses of 6 kg/ha or less on seven representative weeds and some plants of agricultural interest. The series of N,N-di,sec.butylamides studied proved to be effectively phytotoxic on absorption through either the roots or the foliage. As regards the effect of substitution in the nucleus on the phytotoxicity of these amides, 3,5-dihalogenation proved important. The results also showed: 1) the importance of two sec.butyl groups on the amide nitrogen for the appearance of selective phytotoxicity against two grass weeds; 2) the different behaviour of the two acids (XXIa) and (XXIIa) in comparison with the corresponding di,sec.butylamides (XXI) and (XXII); 3) the importance of derivative (IL) which was highly active against graminaceous weeds but showed low phytotoxicity against crop plants, graminaceous ones included.
Aminobenzoates↗
[Phytotoxicity of hydrazones of aromatic aldehydes].
A series of hydrazones of aromatic aldehydes (B) was prepared and tested for phytotoxicity. These compounds are bioisosters of 1-aryltriazenes (A) which were found to possess interesting phytotoxic properties in a previous research. The substances studied (Tables I leads to III: compounds(I leads to CLXXX)) some of which were previously unrecorded, were prepared by the usual procedures from the required aldehyde and hydrazine derivative. The phytotoxicity of all the compounds was studied using seven representative species in both pre- and post-emergence tests at a dose of 6 kg/ha. It was found that this class of compounds shows phytotoxicity by absorption through the foliage with specificity for Amaranthus retroflexus L. The only exceptions are compounds where the aryl residue is 2,6-dichlorophenyl; these compounds show wide spectrum of phytotoxicity by absorption through the leaves.
Aldehydes↗
[Phytotoxicity of di,sec.butylamides of halogenoalkoxybenzoic acids].
N,N-di,sec.butylamides of halogenated alkoxybenzoic acids were prepared and tested for phytotoxic activity. The corresponding acids and a series of N-alkyl- and N,N-dialkylamides of 2-methoxy-3,5-dichlorobenzoic acid were studied in parallel. The phytotoxicity of these substances was tested against seven representative weeds and some crop plants using both pre- and post-emergence test at doses of 6 kg/ha or lower. The amides studied proved more strongly phytotoxic on absorption through the root than through the foliage. Furthermore selective phytotoxic activity against two important infesting graminacae, Echinochloa crus-galli R.S. and Setaria glauca L. was observed. Some of these compounds showed low toxicity or were tolerated by crop plants. The results obtained with this series of amides of 2-methoxy-3,5-dichlorobenzoic acid confirm the importance of the sec.butyl group on N for the appearance of selective phytotoxicity.
Benzoates↗
[Negative geotropic effect and phytotoxicity of N-quinolinphthalamic acids and allied substances].
N-Quinolinphthalamic acids and allied substances have been prepared and studied for negative geotropic effect and phytotoxic activity. The substances (Tables I leads to III) prepared by fusion of the required anhydride and amine were tested to evaluate the negative geotropic effect on germinating roots of Lens esculenta Moench s.1. and phytotoxicity in both pre- and post-emergence tests against five representative weed species at a dose of 6 kg/ha. It was found that substances (I), (VII), (VIII) and (IX) showed negative geotropic effect of the same order of magnitude as that of the reference substance (alpha-naphthylphthalamic acid). Substances (VII), (VIII) and (IX) proved highly active in the phytotoxicity tests. The simultaneous appearance of geotropic and pre-emergence phytotoxic activity seems to be connected with the presence of an 8-quinoline residue on the amide nitrogen.
Herbicides↗
[N,N-Di-(1-ethylpropyl)amides of benzoic and naphthoic acids having phytotoxic activity].
N,N-di-(1-ethylpropyl)amides of benzoic and naphthoic acids suitable substituted in the nucleus were prepared and tested for selective phytotoxic activity in both pre- and post-emergence tests against some weed species. All the amides tested showed good generic phytotoxicity, often with good selectivity, on absorbance through the roots of graminaceous weeds. The nature and degree of phytotoxic activity was influenced by the nature, position and number of substituents on the aromatic nucleus. Confirmation was again obtained of the importance of alpha-substitution in the two alkyl substituents on the amide nitrogen in producing selective phytotoxic activity.
Amides↗
Unveiling the mechanism of micro-and-nano plastic phytotoxicity on terrestrial plants: A comprehensive review of omics approaches.
Micro-and-nano plastics (MNPs) are pervasive in terrestrial ecosystems and represent an increasing threat to plant health; however, the mechanisms underlying their phytotoxicity remain inadequately understood. MNPs can infiltrate plants through roots or leaves, causing a range of toxic effects, including inhibiting water and nutrient uptake, reducing seed germination rates, and impeding photosynthesis, resulting in oxidative damage within the plant system. The effects of MNPs are complex and influenced by various factors including size, shape, functional groups, and concentration. Recent advancements in omics technologies such as proteomics, metabolomics, transcriptomics, and microbiomics, coupled with emerging technologies like 4D omics, phenomics, spatial transcriptomics, and single-cell omics, offer unprecedented insight into the physiological, molecular, and cellular responses of terrestrial plants to MNPs exposure. This literature review synthesizes current findings regarding MNPs-induced phytotoxicity, emphasizing alterations in gene expression, protein synthesis, metabolic pathways, and physiological disruptions as revealed through omics analyses. We summarize how MNPs interact with plant cellular structures, disrupt metabolic processes, and induce oxidative stress, ultimately affecting plant growth and productivity. Furthermore, we have identified critical knowledge gaps and proposed future research directions, highlighting the necessity for integrative omics studies to elucidate the complex pathways of MNPs toxicity in terrestrial plants. In conclusion, this review underscores the potential of omics approaches to elucidate the mechanisms of MNPs-phytotoxicity and to develop strategies for mitigating the environmental impact of MNPs on plant health.
Plants↗
[N-acylindoline with phytotoxic activity. I].
A series of N-acyl derivatives of indoline (A) was prepared and tested for phytotoxic activity. The substances studied (Tables I leads to III, substances I leads to XXVIII) were prepared by reaction of indoline with suitable acylating agents and were mainly new compounds. The biological tests consisted in pre- and post-emergence treatment in doses of 6 kg/ha or lower doses on five common weeds; one substance (XXV) was tested also on other species of economic importance (Table III). The results show that of the three classes studied the N-carbamoyl- and N-thiocarbamoyl derivatives of indoline have wide spectrum phytotoxic activity especialy on absorption via the foliage. The highest phytotoxic activity in both pre- and post-emergence tests was shown by N-(methylcarbamoyl)indoline (XIII) and N-(dimethylcarbamoyl(indoline (XXIII).
Acylation↗
[2-amino-3,5-dichloro-benzoic acid and 3-amino-2,5-dichloro-benzoic acid derivatives with phytotoxic action].
Derivatives of 2-amino-3,5-dichloro- and 3-amino-2,5-dichlorobenzoic acids have been prepared in order to extend previous research regarding the phytotoxicity of these two acids and of the corresponding N,N-di,sec.butylamides. The methyl esters of the two acids, the corresponding acids acetylated on the amino group and their respective methyl esters, and the N,N-di,sec.butylamides acetylated or formylated on the amino group were prepared. All these compounds were subjected to pre- and post-emergence tests using seven representative weeds, using doses of 6 kg/ha and, where substances proved active, at lower doses also. The results showed the importance of the N,N-di,sec.butylamide of 2-amino-3,5-dichlorobenzoic acid which, in contrast to the other derivatives tested, shows selective activity. For 3-amino-2,5-dichlorobenzoic acids and the amides tested, it was confirmed that only the acid shows marked generic phytotoxic activity in both pre- and post-emergence tests. It should be noted that the methyl ester of 3-acetylamino-2,5-dichlorobenzoic acid shows selective phytotoxicity activity.
Chlorobenzoates↗
[Preparation and study of the phytotoxic activity of arylalkylamides. II. N-Phenethylamides].
A series of N-phenetylamides was prepared and tested for phytotoxic activity. Comparison with N-benzylamides showed that lengthening the alkyl chain in the aralkylamide residue reduces phytotoxicity and that, also in the case of phenetylamides, phytotoxic activity is not due to inhibition of the Hill reaction.
Amides↗
[Asymmetric chlorobenzoic acid N,N-dialkylamides having phytotoxic activity].
In continuation of research on phytotoxic substances with selective activity, pre- and post-emergence tests against some weed species were made using a series of 3-chlorobenzamides substituted on the amide nitrogen with a sec.butyl or a 1-methylbutyl group, the second alkyl substituent being linear, branched, saturated or unsaturated. Asymmetric 3-chlorobenzamides with a tert.butyl in place of sec.butyl or with an 1-ethylpropyl in place of 1-methylbutyl and with a second alkyl residue of different nature and with variable weight, were prepared and tested for the purposes of comparison. The results show that amides with excellent phytotoxicity and selectivity of action are obtained if a sec.butyl, 1-methylbutyl or 1-ethylpropyl group is retained and the second substituent on the amide nitrogen is suitably varied. The results give further information on the importance of the steric characteristics of the substituents on nitrogen in the phytotoxic N,N-dialkylamides.
Benzamides↗
[Phytotoxic activity of asymmetric 3,4-dichlorobenzoic acid dialkylamides].
The phytotoxicity of asymmetric N,N-dialkyl-3,4-dichlorobenzamides was studied in pre- and post-emergence tests against some weed species. The amide groups were characterized by the presence of a sec.butyl or 1-methylbutyl group and a variable second alkyl group either linear, branched, saturated or unsaturated. Isomers of the above compounds were also prepared and tested as useful comparison materials; these isomers have n.butyl or ter.butyl in place of sec.butyl or a 1-ethylpropyl in place of 1-methylbutyl or other branched alkyl groups with 5 or 6 carbon atoms, always having a methyl group in the alpha position, in place of the 1-methylbutyl and a second substituent in C2 leads to C4. The results show that compounds with phytotoxicity and selective action as regards Echinochloa and Setaria are obtained if a sec.butyl group, a 1-methylbutyl or a 1-ethylpropyl group is retained and the second substituent on the N-amide is varied appropriately. The compounds with greater phytotoxicity towards the weeds were further tested against some species of agricultural interest.
Benzamides↗
[On the phytotoxicity of some N 1-phenyl-N 1- alkylureas].
A series of N1-phenyl-N1-alkylureas (E) and a series of N-carbamoyl derivatives of tetrahydroquinoline (D) were prepared and studied for phytotoxicity. The substances studied (Tables I, II, substances i leads to xxvii) were mostly new compounds and were prepared from suitable secondary amines by condensation with alkylating agents. Biological tests involved pre- and post-emergence treatment of five common weeds with doses of 6 kg/ha and lower doses (Tables i, ii). The tetrahydroquinoline derivatives (I leads to VII) proved inactive except for the N-dimethylcarbamoyl derivative (III) which on foliar absorption showed selective phytotoxicity against Vicia sativa L. Most of the members of the N1-phenyl-N1-alkylurea class (VIII leads to XXVII) did not have wide spectrum phytotoxicity. Some compounds have however interesting specificity of action against Vicia sativa L.
Alkylation↗
Some phytotoxic glycopeptides from Ceratocystis ulmi, the Dutch Elm Disease pathogen.
Ceratocystis ulmi, the causal agent of Dutch Elm Disease, produces phytotoxic glycopeptides in culture. A mixture of phytotoxic glycopeptides has been prepared by affinity chromatography on a concanavalin A-Sepharose column and collectively they have been termed the toxin. The polydisperse component that makes up the majority of toxin (80%) by weight has a molecular weight of about 2.7.10(5). The large molecular weight component (less than 5%) elutes at the void volume of a Bio-Gel A 50 m column. The other component (15%) appears as a trailing peak on the edge of the major component and has an approximate molecular weight of 7.10(4). The toxin is composed of 83% sugar residues, primarily rhamnose and mannose, and 7% amino acid residues. Methylation analysis coupled with mild acid hydrolysis indicates that the backbone of the polysaccharide portion of the toxin is composed of alpha -1,6-linked mannosyl residues with a 3-linked terminal rhamnosyl residue linked to C-3 of almost every mannosyl residue. The carbohydrate portion of the molecule is linked to the peptide via O-glycosidic linkages to both threonyl and seryl residues. All three components of the toxin are capable of causing wilt in stem cuttings of American elm.
Amino Acids↗
[Optimization of the nutrient medium for the biosynthesis of phytotoxic metabolites of Myrothecium verrucaria VKMF-183].
By means of mathematical planning of the experiment optimal concentrations of components of the nutrient medium were found for the biosynthesis of phytotoxic metabolites by the soil fungus Myrothecium verrucaria VKMF-183. The composition of the optimized medium were: glucose--8%, KH2PO4--0.05%, asparagine--0.35%, ammonium tartrate--0.07%, MgSO4--0.03%, solution of trace elements--0.1%. The accumulation of phytotoxic metabolites in the above medium was 2.4 times higher than in the initial medium.
Culture Media↗
[Phytotoxic activity of triazene derivatives. VI. 1-aryl-3-arylalkyl-3-alkyltriazene derivatives].
A series of of 1-aryl-3-arylalkyl-3-alkyltriazenes (B) was prepared and studied for phytotoxic activity. The previously unknown substances [Table I: substances (I leads to XVI)] were prepared by condensation of the appropriate diazonium salt with the required secondary amine in an alkaline medium and were tested against five representative plant species in both pre- and post-emergence tests at a dose of 6 kg/ha. All the substances studied were inactive in pre-emergence tests. However most of the compounds showed phytotoxic activity by absorption through the foliage. This activity was not very pronounced and always lower than triazene analogs previously studied (type A compounds) which have no aralkyl residue on nitrogen 3.
Herbicides↗
[Asymmetric N,N-dialkyl-3,5-dichlorobenzamides having phytotoxic activity].
Asymmetric N,N-dialkyl-3,5-dichlorobenzamides bearing on the amide N a sec.butyl group or a 1-methylbutyl or 1-ethylpropyl and a second C3 or C4 alkyl group which may be branched or linear, saturated or unsaturated, were prepared and tested for phytotoxicity in pre- and post-emergence experiments. As reference compounds were prepared and tested 3,5-dichlorobenzamides, isomers of the first series, characterized by the presence on the amide N of a n.butyl or ter.butyl in place of the sec.butyl, of a 1-ethylpropyl or other branched alkyl in place of the 1-methylbutyl and a second alkyl group (C2 leads to C4) of varying weight and nature. The results show that all the 3,5-dichlorobenzamides studied have high phytotoxic activity and good selectivity in respect of the two graminaceous weeds tested. The amides proving most active against the weeds were tested against some species of agricultural interest. The substances proving active against the weeds and atoxic for the agrarian species were characterized by the presence on the amide N of a branched C4 or C5 group and a second C3 or C4 group.
Benzamides↗
[Phytotoxic activity of asymmetric N,N-dialkylamides of trisubstituted benzoic acids].
Asimmetric N,N-dialkylamides of benzoic acids variously trisubstituted on the nucleus were prepared and tested for phytotoxicity in pre- and post-emergence experiments. These amides are characterized by the presence on the amidic N of a sec.butyl or a 1-methylbutyl or a 1-ethylpropyl group and a second alkyl group of varying weight and nature. For reference the Authors prepared and studied 2,3,5-trichlorobenzamides bearing on the N atom a tert.butyl and a second linear C2 leads to C4 alkyl. The substances studied generally proved very active against the weeds tested and showed marked specificity of action towards Setaria and Echinochloa. The compounds proving most active against the weeds were also tested against plants of agricultural interest. In general these asymmetric amides proved more phytotoxic against agrarian species than the corresponding N,N-di,sec.butylamides studied previously.
Benzamides↗