Kresoxim-methyl CAS 143390-89-0
Introduction：Basic information about Kresoxim-methyl CAS 143390-89-0, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
Kresoxim-methyl Basic informationAntiseptic Instructions Precautions Uses
| Product Name: | Kresoxim-methyl |
| Synonyms: | BAS 490F;Kresoxim-methyl 250mg [143390-89-0];Methyl (E)-α-(methoxyimino)-2-(2-methylphenoxymethyl)phenylacetate;kresoxim-methyl (ISO) methyl (E)-2-methoxyimino-[2-(o-tolyloxymethyl)phenyl]acetate;Kresoxim-methyl, Methyl (E)-α-(methoxyimino)-2-(2-methylphenoxymethyl)phenylacetate;Cresoxime-methyl;Cygnus;Methyl (E)-2-methoxyimino-2-[2-(o-tolyloxymethyl) phenyl] acetate |
| CAS: | 143390-89-0 |
| MF: | C18H19NO4 |
| MW: | 313.35 |
| EINECS: | 604-351-6 |
| Product Categories: | Amines;Aromatics;Agricultural chemicals(bactericide);Inhibitors;Intermediates & Fine Chemicals;Pharmaceuticals |
| Mol File: | 143390-89-0.mol |
Kresoxim-methyl Chemical Properties
| Melting point | 98-100°C |
| Boiling point | 429.4±47.0 °C(Predicted) |
| density | 1.28 |
| vapor pressure | 2.3 x 10-6 P a (20 °C) |
| storage temp. | Inert atmosphere,2-8°C |
| solubility | Chloroform: Slightly Soluble,Methanol: Slightly Soluble |
| form | Liquid |
| Water Solubility | 2 mg l-1(20 °C) |
| Specific Gravity | 1.28 (20℃) |
| color | Colorless to light yellow |
| BRN | 8330581 |
| Major Application | agriculture cleaning products cosmetics environmental food and beverages personal care |
| InChI | 1S/C18H19NO4/c1-13-8-4-7-11-16(13)23-12-14-9-5-6-10-15(14)17(19-22-3)18(20)21-2/h4-11H,12H2,1-3H3/b19-17+ |
| InChIKey | ZOTBXTZVPHCKPN-HTXNQAPBSA-N |
| SMILES | CO\N=C(\C(=O)OC)c1ccccc1COc2ccccc2C |
| LogP | 3.44 at 25℃ |
| Surface tension | 72.8mN/m at 1.8mg/L and 20℃ |
| CAS DataBase Reference | 143390-89-0(CAS DataBase Reference) |
| EPA Substance Registry System | Kresoxim-methyl (143390-89-0) |
Safety Information
| Hazard Codes | Xn;N,N,Xn |
| Risk Statements | 40-50/53 |
| Safety Statements | 2-36/37-60-61 |
| RIDADR | UN3077 9/PG 3 |
| WGK Germany | 3 |
| HS Code | 29252900 |
| Storage Class | 11 - Combustible Solids |
| Hazard Classifications | Aquatic Acute 1 Aquatic Chronic 1 Carc. 2 |
| Hazardous Substances Data | 143390-89-0(Hazardous Substances Data) |
| Toxicity | LD50 in rats (mg/kg): >5000 orally; >2000 dermally (Ammerman) |
| Antiseptic | Kresoxim-methyl is a high-efficiency, broad-spectrum and novel kind of fungicide. It has excellent treatment efficacy on strawberry powdery mildew, melon powdery mildew, cucumber powdery mildew, pear scab and other diseases. It is capable of controlling the treatment of Ascomycetes, Basidiomycetes, Deuteromycetes, Oomycetes and most kinds of other diseases. It has inhibitory effect on spore germination and growth of mycelium inside the leaf with activities of protection, treatment and eradication. It has good permeability and local systemic activity with long duration period. It has been widely applied for controlling crop diseases on fruit trees, vegetables, tea, tobacco, etc. In addition, the product can have a positive physiological regulatory function on the crop which is capable of inhibiting the generation of ethylene, helping crops have a longer period of time to ensure the energy storage and guarantee the biological maturity; it can significantly improve the crop nitrification reductase activity, when the crop is subject to attack from viruses, it can accelerate the formation rate of resistant virus proteins. |
| Instructions | 30% Kresoxim-methyl suspending agent Wheat, corn: rust, powdery mildew, leaf blight and root rot dosage: 20ml/acre, foliage spray with 2-3 times per quarter. Rice: Rice smut, sheath blight, rice blast dosage: 20ml/acre, apply foliage spray with 2-3 times per quarter. Peanut: leaf spot disease; dosage: 20ml/acre, apply foliage spray with 2-3 times per quarter. Leafy: powdery mildew, anthracnose, downy mildew onion, purpura, celery leaf spot and white cabbage rust dosage: 3000-4000 times, apply foliage spray with 2-3 times per quarter. Flowers: powdery mildew, rust, black spot dosage: 3000-4000 times, apply foliage spray with 2-3 times per quarter. Banana: leaf spot, scab disease Dosage: 3000-4000 times, apply foliage spray with 2-3 times per quarter. Oranges, grapefruit: macular disease, scab and anthracnose and scab dosage: 4000-5000 times, apply foliage spray with 2-3 times per quarter. Beet, strawberry: powdery mildew, downy mildew, and anthracnose as well as leaf blight dosage: 3000-4000 times, apply foliage spray with 2-3 times per quarter. Grapes: powdery mildew, anthracnose and black rot Dosage: 3000-4000 times, apply foliage spray with 2-3 times per quarter. Apple, pear: leaf spot, ring rot, anthracnose, scab, and rust dosage: 4000-5000 times, apply foliage spray with 2-3 times per quarter. Pepper, tomato (Solanaceae): leaf spot, anthracnose, early blight and downy mildew as well as scab dosage: 2000-3000 times, apply foliage spray with 2-3 times per quarter. Melons: powdery mildew, leaf spot and gummy stem blight Dosage: 2000-3000 times, apply foliage spray with 2-3 times per quarter. Beans: rust, powdery mildew, leaf spot dosage: 3000-4000 times, apply foliage spray with 2-3 times per quarter. The above information is edited by the chemicalbook of Dai Xiongfeng. |
| Precautions | 1: Kresoxim-methyl should not be used in combination with strong alkali, strong acidic substances such as pesticides. 2: The safety interval of product is four days with crop being subject to spraying at most at 3-4 times per quarter. 3: People, upon application of this product, should wear masks, gloves and goggles, and should not make things and drinking during spraying and should promptly wash hands and face after spraying. 4: pregnant women and lactating women should not touch. 5: it has certain toxicity on aquatic fishes and should be kept from contaminating surface water. 6: it has excellent efficacy in controlling powdery mildew. Owning to that the powdery mildew fungus is prone to develop drug resistance. Application of Kresoxim-methyl in area had been subject to long-term application of triazole fungicides will achieve more pronounced efficacy and it can be mixed with thiophanate-methyl for application. 7: It should be stored in dry, cool, ventilated, rainproof place and should be away from fire and heat source. It should be put in place out of the reach of children and locked. Avoid storing it together with food, drink and feed. |
| Uses | It is a kind of Strobilurin fungicide and is mainly applied to cereals, rice, potatoes, apples, pears, pumpkins and grapes. It also has protection, treatment and eradication activity on the Ascomycetes, Basidiomycetes, Deuteromycetes and Oomycetes and other pathogenic fungi with long duration period. Under recommended dose, it is safe to crops without injury-free and safe for the environment. |
| Description | Kresoxim-methyl is a strobilurin fungicide. It inhibits conidial germination of V. inaequalis isolates from apple orchards (EC50s = 0.00033-0.0078 mg/L). Kresoxim-methyl also inhibits mycelial growth (EC50 = 0.240 mg/L) and is fungicidal against Saprolegnia (MIC = 1 mg/L). It increases intracellular calcium levels and disrupts the mitochondrial membrane potential in mouse cortical cultures in a concentration-dependent manner. Kresoxim-methyl is toxic to goldfish (C. auratus; LC50 = 0.807 mg/L). |
| Uses | Agricultural fungicide. |
| Uses | An agricultural fungicide. |
| Uses | Kresoxim-methyl is used for the control of several diseases (scab,mildews, blast, sheath blight and others) on a range of crops includingapples, pears, vines, sugar beet and cereals. |
| Definition | ChEBI: A carboxylic ester that is the methyl ester of (2E)-(methoxyimino){2-[(2-methylphenoxy)methyl]phenyl}acetic acid. A fungicide for the control of scab on apples and pears and other fungal diseases on a wide range of crops. |
| Hazard | Moderately toxic by skin contact. Low tox-icity by ingestion and inhalation. |
| Safety Profile | Moderately toxic byskin contact. Low toxicity by ingestion andinhalation. Questionable carcinogen withexperimental data reported. When heated todecomposition it emits toxic vapors of NOx. |
| Synthesis | 67-56-1 137169-29-0 143390-89-0 To the organic layer obtained in Example 12 was added an aqueous solution (132.0 ml) of tetrabutylammonium bromide (TBAB, 0.14 g), sodium hydroxide (15.8 g), and the reaction was stirred at 45°C for 1.0 hour. The organic layer containing methyl 2-o-toluoyloxymethylbenzoate was separated and retained to recover 2-o-toluoylbenzoic acid (compound of formula (1)). To the aqueous layer containing methyl 2-o-toluoyloxybenzoate (compound of formula (4a)) was added an aqueous solution (25.0 ml) of methoxylamine hydrochloride (14.5 g) and stirred at room temperature for 1.0 hour. Dichloromethane (DCM, 35.0 ml) was added to the reaction mixture and stirring was continued for 1.0 hour. The organic layer was separated and the aqueous layer was extracted with DCM (40.0 ml). The organic layers were combined and dried to give a mixture containing methoxyimino-(2-o-toluyloxymethylphenyl)acetic acid (compound of formula (4b)) with a 50:50 ratio of E- and Z-isomers, where R is 2-methylphenoxy. To this organic layer was added N,N-dimethylformamide (DMF, 0.7 ml) at room temperature followed by thionyl chloride (26.3 g). The reaction mixture was heated at 40-45°C for 8.0 hours and concentrated to give a gummy substance. Methanol (100.0 ml) was added to the colloidal substance within 1.0 h. The reaction mixture was heated at 60-65°C for 1.0 h. The mixture was cooled to 10°C and filtered. The white solid was washed with methanol (30 ml) and dried to give (E)-2-(methoxyimino)-2-(2-((tolylmethoxy)methyl)phenyl)acetic acid methyl ester (Kresoxim-methyl, compound of formula (5b)) (42.5 g, 82.2% yield) with HPLC purity >96%. |
| Metabolic pathway | By hepatocyte suspensions prepared from goats, pigs,hens, and rats that have been cryopreserved andthawed, BAS 490 F is metabolized via the samepathways as observed using fresh rat hepatocytes.The rate of hydrolysis of 14C-BAS 490 F leading to acarboxylic acid derivative seems to be constantbetween the cryopreserved and fresh hepatocytesexcept for goats. The oxidation reaction at the methylgroup of the phenoxy ring, leading to thehydroxymethyl analog of the carboxylic acid of BAS490 F, significantly decreases after cryopreservation,whereas the formation of (E)-2-methoxyimino-2[2-(4-hydroxy-2-methylphenyloxymethyl)phenyl] acetic acidby hydroxylation at the 4-position of the phenoxy ringremains at a constant rate. In pig hepatocytes, the twohydroxylated metabolites of the phenoxy ring, carboxyBAS 409 F and (E)-2-methoxyimino-2-o-hydroxymethylphenyl acetic acid, are formed to alesser extent after cryopreservation. |
| Metabolism | Kresoxim-methyl is rapidly metabolized in mammaliansystems to the virtually inactive carboxylic acid, accountingfor its low toxicity and high level of selectivity. Atharvestresidues in cereals and top fruit are <0.05 mg/kgand <1 mg/kg in grapes and vegetables. The soil DT50 =<3 days, and the Koc is 219 to 372. For the main metabolite,the Koc is 17 to 24. Hydrolytic stability tests indicatea DT50 of 34 days at pH 7 but only 7 h at pH 9. |
| Toxicity evaluation | Kresoxim-methyl has an acute oral LD50 > 5,000and an acute dermal LD50 > 2,000 mg/kg in rats. TheNOEL for rats is 800 ppm, and the ADI = 0.4 mg/kg bw(body weight). Kresoxim-methyl is not a skin or eyeirritant, is nonmutagenic and nonteratogenic. It showstoxicity to aquatic organisms (fish 96-h LC50 = 0.681to 1 mg/L) but does not cause permanent damage.Other nontarget organisms show the following levelsof sensitivity: bird: 14-day LD50 = 2,150 mg/kg; bee: 48-h LD50 ≥ 20 μg/bee; worm: LC50 ≥ 937 mg/kg; Daphnia:48-h EC50 = 0.186 mg/L; and algae 0- to 2-h EC50 =63 μg/L. |
| Degradation | Kresoxim-methyl is a stable crystalline solid with limited water solubility.It is stable in the pH range 3-8 but it is hydrolysed to the carboxylic acid(2, see Scheme 1) in base. DT50 values (25 °C) at pH 5,7 and 9 were 875,34and 0.29 days, respectively. The product (2) was stable under theseconditions. Kresoxim-methyl undergoes rapid photodegradation in water whenirradiated with UV light. Its DT50 was 3 days and several products wereformed, one of which was the Z-isomer. Details of the other products arenot available. Under conditions of simulated sunlight the compound wasdegraded with a DT50 of 37 days in pure water and 19 days in naturalpond water. |
| References | [1] Patent: WO2013/144924, 2013, A1. Location in patent: Page/Page column 28; 36 |
Kresoxim-methyl Preparation Products And Raw materials
| Raw materials | Methanol-->Benzeneaceticacid,-(methoxyimino)-2-[(2-methylphenoxy)methyl]--->N,N-Dimethylformamide-->Thionyl chloride |
