Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C12H18N4O6S |
| Molecular Weight | 346.36 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CCCN(CCC)C1=C(C=C(C=C1[N+]([O-])=O)S(N)(=O)=O)[N+]([O-])=O
InChI
InChIKey=UNAHYJYOSSSJHH-UHFFFAOYSA-N
InChI=1S/C12H18N4O6S/c1-3-5-14(6-4-2)12-10(15(17)18)7-9(23(13,21)22)8-11(12)16(19)20/h7-8H,3-6H2,1-2H3,(H2,13,21,22)
| Molecular Formula | C12H18N4O6S |
| Molecular Weight | 346.36 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
Oryzalin is a selective preemergence surface-applied herbicide used for control of annual grasses and broadleaf weeds in fruit trees, nut trees, vineyards, established bermudagrass turf and established ornamentals. It inhibits the growth of germinating weed seeds. Oryzalin is an effective inhibitor of human
carbonic anhydrases (CAs). Eleven out of 12 catalytically active human CAs were strongly
inhibited by oryzalin and exhibited affinities of approximately 2–2000 nM. Oryzalin has been shown to bind specifically to plant tubulin in vitro, inhibited
its polymerization, and partly depolymerize taxol-stabilized
microtubules. It also inhibits polymerization of leishmania microtubules in vitro.
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL261 |
29.0 nM [Ki] | ||
Target ID: CHEMBL205 |
7.8 nM [Ki] | ||
Target ID: CHEMBL3510 |
2.2 nM [Ki] | ||
Target ID: 1.3391069E7 Gene Symbol: LDBPK_130330 |
|||
Target ID: 1.7897544E7 Gene Symbol: CARUB_v10008562mg |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | Unknown Approved UseUnknown |
|||
| Primary | Unknown Approved UseUnknown |
|||
| Primary | Unknown Approved UseUnknown |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Antimitotic agents increase the production of doubled-haploid embryos from cork oak anther culture. | 2007-12 |
|
| Pollen tube growth: coping with mechanical obstacles involves the cytoskeleton. | 2007-07 |
|
| Investigating cytoskeletal function in chloroplast protrusion formation in the arctic-alpine plant Oxyria digyna. | 2007-05 |
|
| Arabidopsis MICROTUBULE-ASSOCIATED PROTEIN18 functions in directional cell growth by destabilizing cortical microtubules. | 2007-03 |
|
| Differential organelle movement on the actin cytoskeleton in lily pollen tubes. | 2007-03 |
|
| Surflan and oryzalin impair reproduction in the teleost medaka (Oryzias latipes). | 2007-03 |
|
| Targeting of TMV movement protein to plasmodesmata requires the actin/ER network: evidence from FRAP. | 2007-01 |
|
| Leishmania tarentolae: purification and characterization of tubulin and its suitability for antileishmanial drug screening. | 2006-12 |
|
| Cytoskeletal asymmetry in Zea mays subsidiary cell mother cells: a monopolar prophase microtubule half-spindle anchors the nucleus to its polar position. | 2006-11 |
|
| The cytoskeleton maintains organelle partitioning required for single-cell C4 photosynthesis in Chenopodiaceae species. | 2006-09 |
|
| Tobacco WLIM1 is a novel F-actin binding protein involved in actin cytoskeleton remodeling. | 2006-09 |
|
| Kinesin-5 motors are required for organization of spindle microtubules in Silvetia compressa zygotes. | 2006-08-31 |
|
| Binding and interaction of dinitroanilines with apicomplexan and kinetoplastid alpha-tubulin. | 2006-08-24 |
|
| Cortical microtubule arrays lose uniform alignment between cells and are oryzalin resistant in the Arabidopsis mutant, radially swollen 6. | 2006-07 |
|
| Effects of de- and rehydration on food-conducting cells in the moss Polytrichum formosum: a cytological study. | 2006-07 |
|
| A MORN-repeat protein is a dynamic component of the Toxoplasma gondii cell division apparatus. | 2006-06-01 |
|
| Survival of adult Tiphia vernalis (Hymenoptera: Tiphiidae) after insecticide, fungicide, and herbicide exposure in laboratory bioassays. | 2006-04 |
|
| Leaching of oryzalin and diuron through undisturbed vineyard soil columns under outdoor conditions. | 2006-03 |
|
| Polarization of the endomembrane system is an early event in fucoid zygote development. | 2006-02-23 |
|
| Cytoskeletal components of an invasion machine--the apical complex of Toxoplasma gondii. | 2006-02 |
|
| Cellular and molecular actions of dinitroaniline and phosphorothioamidate herbicides on Plasmodium falciparum: tubulin as a specific antimalarial target. | 2006-02 |
|
| In vitro polyploidisation in the family of the ranunculaceae. | 2006 |
|
| Hypersensitivity to cytoskeletal antagonists demonstrates microtubule-microfilament cross-talk in the control of root elongation in Arabidopsis thaliana. | 2006 |
|
| The peroxisomal multifunctional protein interacts with cortical microtubules in plant cells. | 2005-11-28 |
|
| Endoplasmic reticulum targeted GFP reveals ER organization in tobacco NT-1 cells during cell division. | 2005-11-07 |
|
| Nod factors alter the microtubule cytoskeleton in Medicago truncatula root hairs to allow root hair reorientation. | 2005-11 |
|
| Toxicity of herbicides in highway runoff. | 2005-09 |
|
| Residential proximity to agricultural pesticide use and incidence of breast cancer in California, 1988-1997. | 2005-08 |
|
| Isolation of a protein interacting with Vfphot1a in guard cells of Vicia faba. | 2005-07 |
|
| Microtubule plus-ends reveal essential links between intracellular polarization and localized modulation of endocytosis during division-plane establishment in plant cells. | 2005-04-14 |
|
| Identification of the herbicide Surflan and its active ingredient oryzalin, a dinitrosulfonamide, as xenoestrogens. | 2005-02 |
|
| XTH acts at the microfibril-matrix interface during cell elongation. | 2005-02 |
|
| Spatial determinants in morphogenesis: recovery from plasmolysis in the diatom Ditylum. | 2005-02 |
|
| [Lectin and mitotic activities in root meristems of winter wheat under oryzalin effect]. | 2005 |
|
| Reorganization and in vivo dynamics of microtubules during Arabidopsis root hair development. | 2004-12 |
|
| In vitro culture of Arabidopsis embryos within their ovules. | 2004-12 |
|
| Oryzalin fate and transport in runoff water in Mediterranean vineyards. | 2004-11 |
|
| Determination of oryzalin in water, citrus fruits, and stone fruits by liquid chromatography with tandem mass spectrometry. | 2004-09-22 |
|
| Low concentrations of propyzamide and oryzalin alter microtubule dynamics in Arabidopsis epidermal cells. | 2004-09 |
|
| Disorganization of cortical microtubules stimulates tangential expansion and reduces the uniformity of cellulose microfibril alignment among cells in the root of Arabidopsis. | 2004-08 |
|
| Herbicide runoff along highways. 2. Sorption control. | 2004-06-15 |
|
| Herbicide runoff along highways. 1. Field observations. | 2004-06-15 |
|
| Cytokinesis in brown algae: studies of asymmetric division in fucoid zygotes. | 2004-06 |
|
| Herbicide loss following application to a railway. | 2004-06 |
|
| The Arabidopsis sku6/spiral1 gene encodes a plus end-localized microtubule-interacting protein involved in directional cell expansion. | 2004-06 |
|
| Microtubules of guard cells are light sensitive. | 2004-05 |
|
| [The roles of microtubule in internodal cell elongation (Nitellopsis obtusa)]. | 2004-04 |
|
| Dynamic cytoskeleton rearrangements in giant cells and syncytia of nematode-infected roots. | 2004-04 |
|
| Expression of an Arabidopsis phosphoglycerate mutase homologue is localized to apical meristems, regulated by hormones, and induced by sedentary plant-parasitic nematodes. | 2003-11 |
|
| Gravisensing: ionic responses, cytoskeleton and amyloplast behavior. | 2003 |
Patents
Sample Use Guides
In Vivo Use Guide
Curator's Comment: Intestinal cryptosporidiosis in rats was treated with oryzalin. The ED50 was determined to be 7 mg/kg using twice daily doses administered for 3 consecutive days. A maximum inhibition of 85.5% was achieved at 25 mg/kg and this inhibition remained constant despite increasing the oryzalin dose to 200 mg/kg.
A total of sixteen 12- to 14-day-old Sprague–Dawley
rats were dosed with a single oral dose of 100 mg/kg
oryzalin.
Route of Administration:
Oral
In Vitro Use Guide
Curator's Comment: Oryzalin inhibited vasopressin, bradykinin and platelet-derived growth factor [Ca2+]i signalling in Swiss 3T3 fibroblasts with IC50 values of 14, 16 and 18 uM, respectively. 45Ca2+ uptake into nonmitochondrial stores of saponin-permeabilized Swiss 3T3 cells was inhibited by oryzalin with an IC50 of 34 uM. Oryzalin inhibited colony formation of HT-29 colon carcinoma cells with an IC50 of 8 uM and inhibited the growth of a number of other cancer cell lines and primary human tumors in vitro with IC50 values in the range 3 to 22 uM. https://www.ncbi.nlm.nih.gov/pubmed/9443610
Replication of wild-type T. gondii is inhibited by 0.5 to 2.5 uM oryzalin.
| Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 19:28:51 GMT 2025
by
admin
on
Mon Mar 31 19:28:51 GMT 2025
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| Record UNII |
662E385DWH
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| Record Status |
Validated (UNII)
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| Record Version |
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EPA PESTICIDE CODE |
104201
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Oryzalin
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oryzalin
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662E385DWH
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m8252
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PRIMARY | Merck Index |