Persistence of Biological Activity and Leaching Potential of Herbicides Aminocyclopyrachlor and Indaziflam in Soils with Different Textures1

Guerra, Naiara; Júnior, Rubem Silvério Oliveira; Constantin, Jamil; Neto, Antônio Mendes Oliveira; Gemelli, Alexandre; Júnior, D. Mattos; Guerra, Angélica

doi:10.1590/s0100-83582016340200016

Cited by 15 publications

(19 citation statements)

References 19 publications

(18 reference statements)

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“…The determination of the more reactive regions, employing the finite difference approximation and defined by equations (10)- (12), are depicted in Figures 4, 5, 6 and 7 for IND, ITI, ICA and FDAT respectively. In the case of an electrophilic attack, IND exhibits the more reactive sites on the benzene ring, while ITI and ICA on the nitrogen atom of the central section of the molecule.…”

Section: Local Reactivity Parametersmentioning

confidence: 99%

“…3 , broken circles show the more reactive zones in each molecule Figure 7. Isosurfaces of the Fukui Functions for FDAT according to equations (10), (11) and (12) at the wB97XD/6-311++G(2d,2p) level of theory employing the PCM solvation model In the case of (a) electrophilic, b) nucleophilic and c) free radical attacks. In all cases the isosurfaces were obtained at 0.008 e/u.a.…”

Section: Local Reactivity Parametersmentioning

confidence: 99%

“…11 In this sense, IND has been detected in soil samples collected at each depth, suggesting movement with irrigation water. 12 Thus, as other pre-emergence herbicides applied to soil, it is necessary to understand the fate and chemical behavior of this herbicide and its metabolites to understand the potential risk of contamination of water resources. 13 Up to the best our knowledge, information published concerning the water contamination caused by IND is scarce, and none concerning any of its metabolites.…”

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confidence: 99%

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Analysis of the Chemical Reactivity of Indaziflam Herbicide and Its Metabolites Through Global and Local Reactivity Descriptors

Mendoza-Huízar

Ríos-Reyes²,

Álvarez-Romero

et al. 2019

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In the present work, the chemical reactivity of indaziflam N-[(1R,2S)-2,3-dihydro-2,6-dimethyl-1H-inden-1-yl]-6-[(1R)-1-16 fluoroethyl]-1,3,5-triazine-2,4-diamine so called indaziflam (IND) and its metabolites: triazine indanone (ITI), indaziflam carboxylic acid (ICA) and fluoroethyldiaminotriazine (FDAT) was analyzed. The calculations were performed at the X/6-311++G(2d,2p) (where X=B3LYP, M06, M06L and wB97XD) level of theory, in the aqueous phase. The results indicate that ITI is the more reactive followed by ICA, IND and FDAT. The distribution of the active sites was determined evaluating the Fukui function employing the frozen core and finite difference approximations. For electrophilic attacks, IND shows the more reactive zone on the benzene ring, ITI and ICA on the nitrogen atom in the central section and FDAT on its nitrogen atoms. The more nucleophilic sites for IND are observed on the carbon atoms of triazine, on the carbonyl group for ITI, on the carboxylic group for ICA, and on the nitrogen atoms of triazine for FDAT. For free radical attacks case, the more reactive sites for IND are on the benzene and triazine rings, on the carbonyl group, nitrogen of the central section, and nitrogen atoms of triazine, for ITI, carboxylic group for ICA, and on the nitrogen atoms of triazine ring for FDAT.

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Section: Local Reactivity Parametersmentioning

confidence: 99%

Section: Local Reactivity Parametersmentioning

confidence: 99%

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confidence: 99%

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Analysis of the Chemical Reactivity of Indaziflam Herbicide and Its Metabolites Through Global and Local Reactivity Descriptors

Mendoza-Huízar

Ríos-Reyes²,

Álvarez-Romero

et al. 2019

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“…As características fisico-químicas são a baixa solubilidade em água (0,0028 kg m -3 a 20 °C), o Koc< 1.000 mL g -1 de carbono orgânico, o Pka de 3,5 e o log Kow em pH 4,7 ou 9 de 2,8 (TOMPKINS, 2010). O indaziflam é caracterizado pela meia-vida de 150 dias, alta persistência no solo (ALONSO et al, 2015, (KAAPRO;HALL, 2012), em soja e beterraba a persistência da atividade biológica do indaziflam foi superior a 150 dias tanto em solo muito argiloso quanto em textura franco-argiloarenosa (GUERRA et al, 2016). Segundo Guerra et al (2013) os metabólitos desse herbicida apresentam alto potencial de lixiviação para água subterrânea, o que faz necessário conhecimento do seu comportamento no solo.…”

Section: Introductionunclassified

Seleção de espécies bioindicadoras para o herbicida indaziflam

Dias

Gomes²,

Anunciato³

et al. 2019

RBHerbicidas

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O herbicida indaziflam apresenta atividade residual no solo e pode se tornar problema para os cultivos agrícolas, pela possibilidade de carryover em culturas sucessoras. Assim, objetivou-se selecionar potenciais espécies bioindicadoras para presença de resíduos do indaziflam no solo. Foram realizados dois experimentos em casa de vegetação, utilizando vasos de polietileno de 0,00025 m3, ambos distribuídos no delineamento em blocos ao acaso com quatro repetições. No primeiro experimento foram utilizadas onze espécies com potencial uso como bioindicadoras: arroz, aveia, beterraba, capim-braquiária, feijão, girassol, milho, pepino, soja, tomate e trigo submetidas à aplicação de sete doses de indaziflam (0; 6,25; 12,5; 25; 50; 75 e 100 g i.a. ha-1). em pré-emergência das culturas. No segundo experimento, cinco sub-doses (0; 0,3906; 0,7812; 1,5625 e 3,125 g i.a. ha-1) do indaziflam foram aplicadas nas espécies que não emergiram na menor dose ou concentração do herbicida no primeiro experimento. Foram avaliadas a fitointoxicação e altura de plantas (ALT) aos 3, 7, 14 e 21 dias após a emergência (DAE). Aos 21 DAE avaliou-se matéria seca de parte aérea (MSPA), de raiz (MSR) e total (MST). O aumento das doses de indaziflam provocou aumento dos sintomas de fitointoxicação e reduções nas variáveis ALT, MSPA, MSR e MST. Entre as espécies avaliadas, em monocotiledôneas na ordem: capim-braquiária, arroz, milho, trigo, aveia e em eudicotiledôneas: tomate, pepino, girassol, feijão, soja apresentam potencial para uso como bioindicadora em estudos com indaziflam. A beterraba apresentou ser extremamente sensível ao herbicida não emergindo em nenhuma das doses estudadas.

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“…This herbicide thus has the potential for long persistence, although the dissipation rate is dependent on several factors including soil type, moisture content, and temperature. Indeed, aminocyclopyrachlor was found to be biologically active for an even longer period of 150 days in two Brazilian soils [11]. Aminocyclopyrachlor mineralization may take place via two different pathways: degradation of the herbicide in the soil by microorganisms and by photolysis when deposited on the soil surface.…”

Section: Introductionmentioning

confidence: 99%

Soil Factors Effects on the Mineralization, Extractable Residue, and Bound Residue Formation of Aminocyclopyrachlor in Three Tropical Soils

et al. 2017

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Abstract:Aminocyclopyrachlor is an herbicide that belongs to the new class of chemicals known as the pyrimidine carboxylic acids, which are used to control broadleaf weeds and brush. However, the environmental behavior and fate of aminocyclopyrachlor are not fully understood. The aim of the present study was thus to evaluate the mineralization, extractable residue and bound residue formation of aminocyclopyrachlor in three tropical soils with different physico-chemical properties. 14 C-labeled [pyrimidine-2-14 C] aminocyclopyrachlor was used to assess the fate of this herbicide in soil placed in biometer culture flasks. Total mineralization (accumulated 14 CO 2 ) of aminocyclopyrachlor was found to be <10% in all soils, decreasing in the following order: Oxisol-Typic Hapludox (clay) > Oxisol-Typic Hapludox (loamy sand) > Plinthosol-Petric (sandy clay). Overall, constant rate of mineralization (k) values for all soils were very low (0.00050% to 0.00079% 14 CO 2 day −1 ), with mineralization half-life times (MT50) consequently very high (877 to 1376 days), suggesting potential long persistence in soil. The amount of extractable residues decreased from~31% to 50% in all soils after 126 days of incubation, indicating an increase in bound residue formation from~5.0-to 7.5-fold compared to evaluation immediately after herbicide application, suggesting that degradation herbicide is involved in the formation of bound residues. Extractable residues are important factors that control mineralization and bound residue formation from aminocyclopyrachlor in the soil. The present study is the first to assess the fate, distribution, and formation of bound residues of aminocyclopyrachlor in soils. Aminocyclopyrachlor residues were predominantly associated with the OM and clay contents of soil. This effect of soil physico-chemical properties should be considered in environmental risk assessment of aminocyclopyrachlor and its application in the field for weed control.

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Persistence of Biological Activity and Leaching Potential of Herbicides Aminocyclopyrachlor and Indaziflam in Soils with Different Textures1

Cited by 15 publications

References 19 publications

Analysis of the Chemical Reactivity of Indaziflam Herbicide and Its Metabolites Through Global and Local Reactivity Descriptors

Analysis of the Chemical Reactivity of Indaziflam Herbicide and Its Metabolites Through Global and Local Reactivity Descriptors

Seleção de espécies bioindicadoras para o herbicida indaziflam

Soil Factors Effects on the Mineralization, Extractable Residue, and Bound Residue Formation of Aminocyclopyrachlor in Three Tropical Soils

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