The Chemistry of Benzothiadiazole Plant Activators

Kunz, W.E.; Schurter, Rolf; Maetzke, Thomas

doi:10.1002/(sici)1096-9063(199708)50:4<275::aid-ps593>3.3.co;2-z

Cited by 11 publications

(12 citation statements)

References 0 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…In Arabidopsis, signaling downstream of SA is mostly controlled by a master regulator called NONEXPRESSOR of PR GENES1 (NPR1), which activates a large set of transcription factors and defense genes (Dong, 2004;Wang et al, 2006;Moore et al, 2011). Benzothiadiazole (BTH) is a functional analog of SA (Kunz et al, 1997) that can induce plant defense responses by activating the expression of defense-related genes downstream of SA (Gorlach et al, 1996;Lawton et al, 1996;Morris et al, 1998;Latunde-Dada & Lucas, 2001). JA is synthesized from the precursor molecule 12-oxo-phytodienoic acid (cis-OPDA) in the peroxisome.…”

Section: Introductionmentioning

confidence: 99%

Salicylic acid activates poplar defense against the biotrophic rust fungusMelampsora larici‐populinavia increased biosynthesis of catechin and proanthocyanidins

et al. 2018

View full text Add to dashboard Cite

Poplar trees synthesize flavan-3-ols (catechin and proanthocyanidins) as a defense against foliar rust fungi, but the regulation of this defense response is poorly understood. Here, we investigated the role of hormones in regulating flavan-3-ol accumulation in poplar during rust infection. We profiled levels of defense hormones, signaling genes, and flavan-3-ol metabolites in black poplar leaves at different stages of rust infection. Hormone levels were manipulated by external sprays, genetic engineering, and drought to reveal their role in rust fungal defenses. Levels of salicylic acid (SA), jasmonic acid, and abscisic acid increased in rust-infected leaves and activated downstream signaling, with SA levels correlating closely with those of flavan-3-ols. Pretreatment with the SA analog benzothiadiazole increased flavan-3-ol accumulation by activating the MYB-bHLH-WD40 complex and reduced rust proliferation. Furthermore, transgenic poplar lines overproducing SA exhibited higher amounts of flavan-3-ols constitutively via the same transcriptional activation mechanism. These findings suggest a strong association among SA, flavan-3-ol biosynthesis, and rust resistance in poplars. Abscisic acid also promoted poplar defense against rust infection, but likely through stomatal immunity independent of flavan-3-ols. Jasmonic acid did not confer any apparent defense responses to the fungal pathogen. We conclude that SA activates flavan-3-ol biosynthesis in poplar against rust infection.

show abstract

Section: Introductionmentioning

confidence: 99%

Salicylic acid activates poplar defense against the biotrophic rust fungusMelampsora larici‐populinavia increased biosynthesis of catechin and proanthocyanidins

et al. 2018

View full text Add to dashboard Cite

show abstract

“…We triggered the SAR pathway with a mimic of salicylic acid-benzo (1,2,3) thiadiazole-7-carbothioic acid (S) methyl ester (BTH; Bion ; Actigard ). BTH is commercially sold as an elicitor of SAR in various crops (Kunz et al, 1997). The induction of the salicylic pathway by BTH applications was revealed through the analyses of several PR protein classes known to be induced by salicylic acid.…”

Section: Introductionmentioning

confidence: 99%

Induction of systemic acquired resistance in cotton by BTH has a negligible effect on phytophagous insects

Inbar

Doostdar

Gerling

et al. 2001

Entomologia Exp Applicata

View full text Add to dashboard Cite

Whether or not chemical changes in plants in response to pests (insects and pathogens) are general or specific remains unclear. Some evidence indicates that an induced response (IR) to arthropods via the octadecanoid pathway represents a distinct mechanism from the salicylic acid-based pathway of systemic acquired resistance (SAR) to pathogens. To further test this hypothesis, young cotton seedlings were activated with benzo (1,2,3) thiadiazole-7carbothioic acid (S) methyl ester (BTH), an elicitor of SAR. The enzymatic activities of a number of pathogenesisrelated (PR) proteins in young and old leaves of control and BTH treated plants were measured. BTH applications elicited marked increases in the activity levels of chitinase, peroxidase, and β-1,3-glucanase both locally and systemically. The highest levels of induction were detected systemically in young leaves. Except for some local effects on whitefly oviposition, the induction of SAR by BTH had no effect on either host preference of whiteflies Bemisia tabaci (Gennadius) or on feeding efficiency of cotton bollworms Helicoverpa armigera (Hübner). We conclude that SAR induction via the salicylic acid pathway in 'Acala' cotton has negligible effect on the tested insect herbivores.

show abstract

“…The structure was solved by direct methods and refined on F 2 by full-matrix least-squares procedures using the SHELXL-97 package. The crystal structure (C 11 H 10 BrN 3 O 2 S, Mr = 327.18) is monoclinic, space group Cc, with unit cell parameters a = 9.262(3), b = 20.328 (7), c = 7.661(3) Å, α = 90˚, β = 120.413(5)˚, γ = 90˚, Z = 4, V = 1244.0(7) Å 3 , F (000) = 652. Goodness-of-fit on F 2 is 0.925.…”

Section: The Synthesis Of Compound 2amentioning

confidence: 99%

“…In the investigation of new agrochemicals, we found that 1,2,3-thiadiazole derivatives have good biological activities [6,7,8,9,10], such as, 1,2,3-thiadiazole-5-formamides possessed excellent fungicidial activity [11], We became interested in making 1,2,3-thiadiazoleacetamide analogues of the lead 1,2,3-thiadiazole-4-formamide, due to their high fungicide activity. Their antiviral activity against HBV was discovered by the random screening in the Hep-G2 cells assay.…”

mentioning

confidence: 99%

Synthesis, X‐ray crystal structure and biological activities of α‐phenoxyl‐1,2,3‐thiadiazoleacetamide

Zhao

2003

Journal of Heterocyclic Chem

View full text Add to dashboard Cite

The annelation of 1,2,3-thiadiazole rings was accomplished by the reaction of N-acylhydrazone 2a bearing an adjacent α α-methyl with thionyl chloride to give α-chloro-N-methyl-1,2,3-thiadiazole-4-acetamide 4 and was demonstrated by the X-ray crystal structure of its derivative 5a. A novel series of α-substituted phenoxy-N-methyl-1,2,3-thiadiazole-4-acetamide 5 were synthesized through the reaction of the compound 4 and phenols. The results of bioassays show that the title compounds exhibit good anti-HBV activities. The crystal of compound 5a, N-methyl-α α-2-bromophenyl-1,2,3-thiadiazole-4-acetamide, has been prepared and determined by X-ray diffraction.

show abstract

The Chemistry of Benzothiadiazole Plant Activators

Cited by 11 publications

References 0 publications

Salicylic acid activates poplar defense against the biotrophic rust fungusMelampsora larici‐populinavia increased biosynthesis of catechin and proanthocyanidins

Salicylic acid activates poplar defense against the biotrophic rust fungusMelampsora larici‐populinavia increased biosynthesis of catechin and proanthocyanidins

Induction of systemic acquired resistance in cotton by BTH has a negligible effect on phytophagous insects

Synthesis, X‐ray crystal structure and biological activities of α‐phenoxyl‐1,2,3‐thiadiazoleacetamide

Contact Info

Product

Resources

About