thiencarbazone-methyl (CHEBI:145500)

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CHEBI:145500 - thiencarbazone-methyl

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ChEBI Name	thiencarbazone-methyl

ChEBI ID	CHEBI:145500

Definition	An N-sulfonylurea in which the sulfur atom is attached to a 4-(methoxycarbonyl)-2-methylthiophen-3-yl group and in which the non-sulfonated nitrogen is substituted by a 3-methoxy-4-methyl-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl group. It is a herbicide used for the selective control of grasses and broadleaf weeds primarily in corn.

Stars	This entity has been manually annotated by the ChEBI Team.

Supplier Information	eMolecules:29533907, eMolecules:36753297, ZINC000026011099

Download	Molfile XML SDF

more structures >>

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The Resolver thinks Mol

6R5 - Ideal conformer

RDKit 3D

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Time for openFile(6R5 - Ideal conformer

RDKit 3D

39 40 0 0 0 0 0 0 0 0999 V2000

-2.5970 -0.6230 -0.6880 C 0 0 0 0 0 0 0 0 0 0 0 0

0.4720 1.9700 0.3020 O 0 0 0 0 0 0 0 0 0 0 0 0

0.9330 0.8770 0.5670 C 0 0 0 0 0 0 0 0 0 0 0 0

0.2030 -0.0080 1.2760 N 0 0 0 0 0 0 0 0 0 0 0 0

-1.3670 0.3410 1.6690 S 0 0 0 0 0 0 0 0 0 0 0 0

-2.2610 0.4980 0.1590 C 0 0 0 0 0 0 0 0 0 0 0 0

-2.6950 1.6590 -0.3170 C 0 0 0 0 0 0 0 0 0 0 0 0

-2.4900 2.9920 0.3550 C 0 0 0 0 0 0 0 0 0 0 0 0

-3.5400 1.4260 -1.8370 S 0 0 0 0 0 0 0 0 0 0 0 0

-3.2890 -0.2600 -1.8020 C 0 0 0 0 0 0 0 0 0 0 0 0

-2.2230 -2.0110 -0.3820 C 0 0 0 0 0 0 0 0 0 0 0 0

-2.6790 -3.0180 -1.1540 O 0 0 0 0 0 0 0 0 0 0 0 0

-2.2700 -4.3630 -0.7930 C 0 0 0 0 0 0 0 0 0 0 0 0

-1.5030 -2.2520 0.5670 O 0 0 0 0 0 0 0 0 0 0 0 0

-1.8820 -0.8120 2.3220 O 0 0 0 0 0 0 0 0 0 0 0 0

-1.3550 1.6310 2.2650 O 0 0 0 0 0 0 0 0 0 0 0 0

2.1720 0.5500 0.1530 N 0 0 0 0 0 0 0 0 0 0 0 0

2.8300 -0.6670 0.3820 N 0 0 0 0 0 0 0 0 0 0 0 0

4.0040 -0.6010 -0.1730 C 0 0 0 0 0 0 0 0 0 0 0 0

4.9360 -1.5840 -0.1680 O 0 0 0 0 0 0 0 0 0 0 0 0

4.5960 -2.7970 0.5080 C 0 0 0 0 0 0 0 0 0 0 0 0

4.1420 0.6320 -0.7660 N 0 0 0 0 0 0 0 0 0 0 0 0

5.3200 1.1040 -1.4980 C 0 0 0 0 0 0 0 0 0 0 0 0

3.0070 1.3300 -0.5640 C 0 0 0 0 0 0 0 0 0 0 0 0

2.7800 2.4610 -0.9520 O 0 0 0 0 0 0 0 0 0 0 0 0

0.5980 -0.8490 1.5540 H 0 0 0 0 0 0 0 0 0 0 0 0

-1.5020 3.3780 0.1030 H 0 0 0 0 0 0 0 0 0 0 0 0

-3.2510 3.6930 0.0120 H 0 0 0 0 0 0 0 0 0 0 0 0

-2.5680 2.8700 1.4350 H 0 0 0 0 0 0 0 0 0 0 0 0

-3.6340 -0.9470 -2.5610 H 0 0 0 0 0 0 0 0 0 0 0 0

-1.1830 -4.4350 -0.8300 H 0 0 0 0 0 0 0 0 0 0 0 0

-2.6140 -4.5890 0.2160 H 0 0 0 0 0 0 0 0 0 0 0 0

-2.7050 -5.0760 -1.4930 H 0 0 0 0 0 0 0 0 0 0 0 0

4.3900 -2.5830 1.5560 H 0 0 0 0 0 0 0 0 0 0 0 0

3.7110 -3.2340 0.0450 H 0 0 0 0 0 0 0 0 0 0 0 0

5.4280 -3.4980 0.4360 H 0 0 0 0 0 0 0 0 0 0 0 0

5.2210 0.8440 -2.5530 H 0 0 0 0 0 0 0 0 0 0 0 0

5.4030 2.1860 -1.3960 H 0 0 0 0 0 0 0 0 0 0 0 0

6.2140 0.6310 -1.0910 H 0 0 0 0 0 0 0 0 0 0 0 0

14 11 2 0

13 12 1 0

12 11 1 0

11 1 1 0

25 24 2 0

23 22 1 0

1 10 2 0

1 6 1 0

15 5 2 0

24 22 1 0

24 17 1 0

10 9 1 0

22 19 1 0

4 5 1 0

4 3 1 0

6 5 1 0

6 7 2 0

5 16 2 0

17 3 1 0

17 18 1 0

19 20 1 0

19 18 2 0

3 2 2 0

9 7 1 0

20 21 1 0

7 8 1 0

4 26 1 0

8 27 1 0

8 28 1 0

8 29 1 0

10 30 1 0

13 31 1 0

13 32 1 0

13 33 1 0

21 34 1 0

21 35 1 0

21 36 1 0

23 37 1 0

23 38 1 0

23 39 1 0

M END): 32 ms

reading 39 atoms

ModelSet: haveSymmetry:false haveUnitcells:false haveFractionalCoord:false

1 model in this collection. Use getProperty "modelInfo" or getProperty "auxiliaryInfo" to inspect them.

Default Van der Waals type for model set to Babel

39 atoms created

ModelSet: not autobonding; use forceAutobond=true to force automatic bond creation

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Molfile expand

Formula

C12H14N4O7S2

Net Charge

Average Mass

390.390

Monoisotopic Mass

390.03039

InChI

InChI=1S/C12H14N4O7S2/c1-6-8(7(5-24-6)9(17)22-3)25(20,21)14-10(18)16-12(19)15(2)11(13-16)23-4/h5H,1-4H3,(H,14,18)

InChIKey

XSKZXGDFSCCXQX-UHFFFAOYSA-N

SMILES

S(NC(=O)N1C(N(C(=N1)OC)C)=O)(C2=C(SC=C2C(=O)OC)C)(=O)=O

Roles Classification
Biological Role(s):	EC 2.2.1.6 (acetolactate synthase) inhibitor An EC 2.2.1.* (transketolase/transaldolase) inhibitor that interferes with the action of acetolactate synthase (EC 2.2.1.6).

Application(s):	herbicide A substance used to destroy plant pests. agrochemical An agrochemical is a substance that is used in agriculture or horticulture.

View more via ChEBI Ontology

ChEBI Ontology
Outgoing	thiencarbazone-methyl (CHEBI:145500) has functional parent thiencarbazone (CHEBI:145501) thiencarbazone-methyl (CHEBI:145500) has role agrochemical (CHEBI:33286) thiencarbazone-methyl (CHEBI:145500) has role EC 2.2.1.6 (acetolactate synthase) inhibitor (CHEBI:22180) thiencarbazone-methyl (CHEBI:145500) has role herbicide (CHEBI:24527) thiencarbazone-methyl (CHEBI:145500) is a N-sulfonylurea (CHEBI:76983) thiencarbazone-methyl (CHEBI:145500) is a ether (CHEBI:25698) thiencarbazone-methyl (CHEBI:145500) is a methyl ester (CHEBI:25248) thiencarbazone-methyl (CHEBI:145500) is a thiophenes (CHEBI:26961) thiencarbazone-methyl (CHEBI:145500) is a triazoles (CHEBI:35727)

IUPAC Name

methyl 4-{[(3-methoxy-4-methyl-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl)carbonyl]sulfamoyl}-5-methylthiophene-3-carboxylate

Synonyms	Sources
3-[N-[(4,5-dihydro-3-methoxy-4-methyl-5-oxo-1H-1,2,4-triazole-1-yl)carbonyl]sulfamoyl]-2-methyl-4-thiophenecarboxylic acid methyl ester	ChEBI
BYH 18636	PPDB
methyl 4-[(4,5-dihydro-3-methoxy-4-methyl-5-oxo-1H-1,2,4-triazol-1-yl)carbonylsulfamoyl]-5-methylthiophene-3-carboxylate	Alan Wood's Pesticides
methyl 4-[(4,5-dihydro-3-methoxy-4-methyl-5-oxo-1H-1,2,4-triazol-1-yl)carboxamidosulfonyl]-5-methylthiophene-3-carboxylate	ChEBI
methyl 4-[[[(4,5-dihydro-3-methoxy-4-methyl-5-oxo-1H-1,2,4-triazol-1-yl)carbonyl]amino]sulfonyl]-5-methyl-3-thiophenecarboxylate	Alan Wood's Pesticides
TCM	PPDB

Brand Names	Sources
Adengo	ChEBI
Autumn	ChEBI
Capreno	ChEBI
Celsius	ChEBI
Corvus	ChEBI
Velocity	ChEBI

Manual Xrefs	Databases
/derivatives/thiencarbazone-methyl	Alan Wood's Pesticides
1241	PPDB
6R5	PDBeChem
View more database links

Registry Numbers	Types	Sources
11327106	Reaxys Registry Number	Reaxys
317815-83-1	CAS Registry Number	ChemIDplus

Citations

Burns EE, Keith BK, Refai MY, Bothner B, Dyer WE (2017)
Proteomic and biochemical assays of glutathione-related proteins in susceptible and multiple herbicide resistant Avena fatua L.
Pesticide biochemistry and physiology 140, 69-78 [PubMed:28755697]
[show Abstract]
Extensive herbicide usage has led to the evolution of resistant weed populations that cause substantial crop yield losses and increase production costs. The multiple herbicide resistant (MHR) Avena fatua L. populations utilized in this study are resistant to members of all selective herbicide families, across five modes of action, available for A. fatua control in U.S. small grain production, and thus pose significant agronomic and economic threats. Resistance to ALS and ACCase inhibitors is not conferred by target site mutations, indicating that non-target site resistance mechanisms are involved. To investigate the potential involvement of glutathione-related enzymes in the MHR phenotype, we used a combination of proteomic, biochemical, and immunological approaches to compare their constitutive activities in herbicide susceptible (HS1 and HS2) and MHR (MHR3 and MHR4) A. fatua plants. Proteomic analysis identified three tau and one phi glutathione S-transferases (GSTs) present at higher levels in MHR compared to HS plants, while immunoassays revealed elevated levels of lambda, phi, and tau GSTs. GST specific activity towards 1-chloro-2,4-dinitrobenzene was 1.2-fold higher in MHR4 than in HS1 plants and 1.3- and 1.2-fold higher in MHR3 than in HS1 and HS2 plants, respectively. However, GST specific activities towards fenoxaprop-P-ethyl and imazamethabenz-methyl were not different between untreated MHR and HS plants. Dehydroascorbate reductase specific activity was 1.4-fold higher in MHR than HS plants. Pretreatment with the GST inhibitor NBD-Cl did not affect MHR sensitivity to fenoxaprop-P-ethyl application, while the herbicide safener and GST inducer mefenpyr reduced the efficacy of low doses of fenoxaprop-P-ethyl on MHR4 but not MHR3 plants. Mefenpyr treatment also partially reduced the efficacy of thiencarbazone-methyl or mesosulfuron-methyl on MHR3 or MHR4 plants, respectively. Overall, the GSTs described here are not directly involved in enhanced rates of fenoxaprop-P-ethyl or imazamethabenz-methyl metabolism in MHR A. fatua. Instead, we propose that the constitutively elevated GST proteins and related enzymes in MHR plants are representative of a larger, more global suite of abiotic stress-related changes.

Garcia MD, Nouwens A, Lonhienne TG, Guddat LW (2017)
Comprehensive understanding of acetohydroxyacid synthase inhibition by different herbicide families.
Proceedings of the National Academy of Sciences of the United States of America 114, E1091-E1100 [PubMed:28137884]
[show Abstract]

Wiggins MS, McClure MA, Hayes RM, Steckel LE (2015)
Integrating Cover Crops and POST Herbicides for Glyphosate-Resistant Palmer Amaranth (Amaranthus palmeri) Control in Corn
Weed Technology. 29, 412-418 [Agricola:IND604666673]
[show Abstract]

Tao Y, Xu J, Liu X, Cheng Y, Liu N, Chen Z, Dong F, Zheng Y (2014)
A quick, easy, cheap, effective, rugged, and safe method for the simultaneous detection of four triazolone herbicides in cereals combined with ultrahigh performance liquid chromatography with tandem mass spectrometry.
Journal of separation science 37, 2340-2348 [PubMed:24923624]
[show Abstract]

Leonie W, Kraehmer H, Santel HJ, Claupein W, Gerhards R (2014)
Thiencarbazone-Methyl Efficacy, Absorption, Translocation, and Metabolism in Vining Weed Species
Weed Science. 62, 512-519 [Agricola:IND601309725]
[show Abstract]

Last Modified

26 November 2019

CHEBI:145500 - thiencarbazone-methyl

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