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143390-89-0

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143390-89-0 Usage

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 lookchem 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

Different sources of media describe the Uses of 143390-89-0 differently. You can refer to the following data:
1. 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.
2. Agricultural fungicide.
3. An agricultural fungicide.
4. Kresoxim-methyl is used for the control of several diseases (scab, mildews, blast, sheath blight and others) on a range of crops including apples, pears, vines, sugar beet and cereals.

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).

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 by skin contact. Low toxicity by ingestion and inhalation. Questionable carcinogen with experimental data reported. When heated to decomposition it emits toxic vapors of NOx.

Metabolic pathway

By hepatocyte suspensions prepared from goats, pigs, hens, and rats that have been cryopreserved and thawed, BAS 490 F is metabolized via the same pathways as observed using fresh rat hepatocytes. The rate of hydrolysis of 14C-BAS 490 F leading to a carboxylic acid derivative seems to be constant between the cryopreserved and fresh hepatocytes except for goats. The oxidation reaction at the methyl group of the phenoxy ring, leading to the hydroxymethyl analog of the carboxylic acid of BAS 490 F, significantly decreases after cryopreservation, whereas the formation of (E)-2-methoxyimino-2[2-(4- hydroxy-2-methylphenyloxymethyl)phenyl] acetic acid by hydroxylation at the 4-position of the phenoxy ring remains at a constant rate. In pig hepatocytes, the two hydroxylated metabolites of the phenoxy ring, carboxy BAS 409 F and (E)-2-methoxyimino-2-o- hydroxymethylphenyl acetic acid, are formed to a lesser extent after cryopreservation.

Metabolism

Kresoxim-methyl is rapidly metabolized in mammalian systems to the virtually inactive carboxylic acid, accounting for its low toxicity and high level of selectivity. Atharvest residues in cereals and top fruit are <0.05 mg/kg and <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 indicate a DT50 of 34 days at pH 7 but only 7 h at pH 9.

Toxicity evaluation

Kresoxim-methyl has an acute oral LD50 > 5,000 and an acute dermal LD50 > 2,000 mg/kg in rats. The NOEL for rats is 800 ppm, and the ADI = 0.4 mg/kg bw (body weight). Kresoxim-methyl is not a skin or eye irritant, is nonmutagenic and nonteratogenic. It shows toxicity to aquatic organisms (fish 96-h LC50 = 0.681 to 1 mg/L) but does not cause permanent damage. Other nontarget organisms show the following levels of 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 875,34 and 0.29 days, respectively. The product (2) was stable under these conditions. Kresoxim-methyl undergoes rapid photodegradation in water when irradiated with UV light. Its DT50 was 3 days and several products were formed, one of which was the Z-isomer. Details of the other products are not available. Under conditions of simulated sunlight the compound was degraded with a DT50 of 37 days in pure water and 19 days in natural pond water.

Check Digit Verification of cas no

The CAS Registry Mumber 143390-89-0 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,4,3,3,9 and 0 respectively; the second part has 2 digits, 8 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 143390-89:
(8*1)+(7*4)+(6*3)+(5*3)+(4*9)+(3*0)+(2*8)+(1*9)=130
130 % 10 = 0
So 143390-89-0 is a valid CAS Registry Number.
InChI:InChI=1/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+

143390-89-0 Well-known Company Product Price

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  • Sigma-Aldrich

  • (37899)  Kresoxim-methyl  PESTANAL®, analytical standard

  • 143390-89-0

  • 37899-100MG

  • 1,020.24CNY

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143390-89-0SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 17, 2017

Revision Date: Aug 17, 2017

1.Identification

1.1 GHS Product identifier

Product name kresoxim-methyl

1.2 Other means of identification

Product number -
Other names methyl (αE)-α-(methoxyimino)-2-[(2-methylphenoxy)methyl]benzeneacetate

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:143390-89-0 SDS

143390-89-0Synthetic route

N-methoxylamine hydrochloride
593-56-6

N-methoxylamine hydrochloride

2-oxo-2-(((o-tolyl)oxymethyl)phenyl)acetic acid methyl ester
143211-10-3

2-oxo-2-(((o-tolyl)oxymethyl)phenyl)acetic acid methyl ester

methyl (E)-2-methoxyimino-2-[2-(o-tolyloxymethyl)phenyl]acetate
143390-89-0

methyl (E)-2-methoxyimino-2-[2-(o-tolyloxymethyl)phenyl]acetate

Conditions
ConditionsYield
In methanol for 6h; Reflux;84.8%
ortho-cresol
95-48-7

ortho-cresol

methyl (E)-2-[2-(bromomethyl)phenyl]-2-(methoxyimino)acetate
133409-72-0

methyl (E)-2-[2-(bromomethyl)phenyl]-2-(methoxyimino)acetate

methyl (E)-2-methoxyimino-2-[2-(o-tolyloxymethyl)phenyl]acetate
143390-89-0

methyl (E)-2-methoxyimino-2-[2-(o-tolyloxymethyl)phenyl]acetate

Conditions
ConditionsYield
With copper(l) iodide In butanone for 4h; Concentration; Reagent/catalyst; Reflux;80%
N-methoxylamine hydrochloride
593-56-6

N-methoxylamine hydrochloride

2-oxo-2-(((o-tolyl)oxymethyl)phenyl)acetic acid methyl ester
143211-10-3

2-oxo-2-(((o-tolyl)oxymethyl)phenyl)acetic acid methyl ester

A

methyl (E)-2-methoxyimino-2-[2-(o-tolyloxymethyl)phenyl]acetate
143390-89-0

methyl (E)-2-methoxyimino-2-[2-(o-tolyloxymethyl)phenyl]acetate

B

methyl (Z)-O-methyloximino-2-[(2-methyl)phenoxymethyl]phenylacetate
248582-68-5

methyl (Z)-O-methyloximino-2-[(2-methyl)phenoxymethyl]phenylacetate

Conditions
ConditionsYield
In pyridine at 20℃; for 17.5h; Condensation;A 63%
B 28%
methyl (Z)-O-methyloximino-2-[(2-methyl)phenoxymethyl]phenylacetate
248582-68-5

methyl (Z)-O-methyloximino-2-[(2-methyl)phenoxymethyl]phenylacetate

methyl (E)-2-methoxyimino-2-[2-(o-tolyloxymethyl)phenyl]acetate
143390-89-0

methyl (E)-2-methoxyimino-2-[2-(o-tolyloxymethyl)phenyl]acetate

Conditions
ConditionsYield
With iodine In benzene at 63℃; for 120h; Isomerization; UV-irradiation;
2-(2-methylphenoxymethyl)phenylzinc chloride

2-(2-methylphenoxymethyl)phenylzinc chloride

methyl (E)-2-methoxyimino-2-[2-(o-tolyloxymethyl)phenyl]acetate
143390-89-0

methyl (E)-2-methoxyimino-2-[2-(o-tolyloxymethyl)phenyl]acetate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 61 percent / Pd(PPh3)4 / tetrahydrofuran / 4 h / 0 °C
2: 63 percent / pyridine / 17.5 h / 20 °C
View Scheme
Multi-step reaction with 3 steps
1: 61 percent / Pd(PPh3)4 / tetrahydrofuran / 4 h / 0 °C
2: 28 percent / pyridine / 17.5 h / 20 °C
3: I2 / benzene / 120 h / 63 °C / UV-irradiation
View Scheme
2-oxo-2-(((o-tolyl)oxymethyl)phenyl)acetic acid methyl ester
143211-10-3

2-oxo-2-(((o-tolyl)oxymethyl)phenyl)acetic acid methyl ester

methyl (E)-2-methoxyimino-2-[2-(o-tolyloxymethyl)phenyl]acetate
143390-89-0

methyl (E)-2-methoxyimino-2-[2-(o-tolyloxymethyl)phenyl]acetate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 28 percent / pyridine / 17.5 h / 20 °C
2: I2 / benzene / 120 h / 63 °C / UV-irradiation
View Scheme
methyl 2-(2-methylphenoxymethyl)phenylglyoxylate dimethyl acetal
143390-88-9

methyl 2-(2-methylphenoxymethyl)phenylglyoxylate dimethyl acetal

N-methoxylamine hydrochloride
593-56-6

N-methoxylamine hydrochloride

2-oxo-2-(((o-tolyl)oxymethyl)phenyl)acetic acid methyl ester
143211-10-3

2-oxo-2-(((o-tolyl)oxymethyl)phenyl)acetic acid methyl ester

methyl (E)-2-methoxyimino-2-[2-(o-tolyloxymethyl)phenyl]acetate
143390-89-0

methyl (E)-2-methoxyimino-2-[2-(o-tolyloxymethyl)phenyl]acetate

Conditions
ConditionsYield
With hydrogenchloride In methanol; dichloromethane
methyl E-2-(2-methylphenoxymethyl)phenylglyoxylate oxime
150869-72-0

methyl E-2-(2-methylphenoxymethyl)phenylglyoxylate oxime

methylene chloride
74-87-3

methylene chloride

methyl (E)-2-methoxyimino-2-[2-(o-tolyloxymethyl)phenyl]acetate
143390-89-0

methyl (E)-2-methoxyimino-2-[2-(o-tolyloxymethyl)phenyl]acetate

Conditions
ConditionsYield
With sodium methylate In 1-methyl-pyrrolidin-2-one; methanol; diethyl ether
(E)-methyl 2-(2-(chloromethyl)phenyl)-2-(methoxyimino)acetate
189813-45-4

(E)-methyl 2-(2-(chloromethyl)phenyl)-2-(methoxyimino)acetate

ortho-cresol
95-48-7

ortho-cresol

methyl (E)-2-methoxyimino-2-[2-(o-tolyloxymethyl)phenyl]acetate
143390-89-0

methyl (E)-2-methoxyimino-2-[2-(o-tolyloxymethyl)phenyl]acetate

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 20 - 50℃; for 64h;
2-[(2-methylphenoxy)methyl]benzoic acid
108475-90-7

2-[(2-methylphenoxy)methyl]benzoic acid

methyl (E)-2-methoxyimino-2-[2-(o-tolyloxymethyl)phenyl]acetate
143390-89-0

methyl (E)-2-methoxyimino-2-[2-(o-tolyloxymethyl)phenyl]acetate

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: thionyl chloride / 3 h / Reflux
2.1: tetrabutylammomium bromide / toluene / 2.5 h / 20 - 35 °C
3.1: hydrogenchloride; acetic anhydride / tert-butyl methyl ether / 10 h / -5 - 30 °C
3.2: 5 h / Reflux
4.1: methanol / 6 h / Reflux
View Scheme
2-[(2-methylphenoxy)methyl]benzoyl chloride
143211-21-6

2-[(2-methylphenoxy)methyl]benzoyl chloride

methyl (E)-2-methoxyimino-2-[2-(o-tolyloxymethyl)phenyl]acetate
143390-89-0

methyl (E)-2-methoxyimino-2-[2-(o-tolyloxymethyl)phenyl]acetate

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: tetrabutylammomium bromide / toluene / 2.5 h / 20 - 35 °C
2.1: hydrogenchloride; acetic anhydride / tert-butyl methyl ether / 10 h / -5 - 30 °C
2.2: 5 h / Reflux
3.1: methanol / 6 h / Reflux
View Scheme
2-[(2-methylphenoxy)methyl]benzoyl cyanide
143211-11-4

2-[(2-methylphenoxy)methyl]benzoyl cyanide

methyl (E)-2-methoxyimino-2-[2-(o-tolyloxymethyl)phenyl]acetate
143390-89-0

methyl (E)-2-methoxyimino-2-[2-(o-tolyloxymethyl)phenyl]acetate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: hydrogenchloride; acetic anhydride / tert-butyl methyl ether / 10 h / -5 - 30 °C
1.2: 5 h / Reflux
2.1: methanol / 6 h / Reflux
View Scheme
methanol
67-56-1

methanol

2-methoxyimino(2-(o-tolyl)oxymethylphenyl)acetic acid
137169-29-0

2-methoxyimino(2-(o-tolyl)oxymethylphenyl)acetic acid

methyl (E)-2-methoxyimino-2-[2-(o-tolyloxymethyl)phenyl]acetate
143390-89-0

methyl (E)-2-methoxyimino-2-[2-(o-tolyloxymethyl)phenyl]acetate

Conditions
ConditionsYield
Stage #1: 2-methoxyimino(2-(o-tolyl)oxymethylphenyl)acetic acid With thionyl chloride In N,N-dimethyl-formamide at 40 - 45℃; for 8h;
Stage #2: methanol at 60 - 65℃; for 2h;
42.5 g
ortho-cresol
95-48-7

ortho-cresol

methyl (E)-2-methoxyimino-2-[2-(o-tolyloxymethyl)phenyl]acetate
143390-89-0

methyl (E)-2-methoxyimino-2-[2-(o-tolyloxymethyl)phenyl]acetate

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: sodium methylate / methanol / 1 h / 20 °C
1.2: 2 h / 190 °C
2.1: thionyl chloride / 3 h / Reflux
3.1: tetrabutylammomium bromide / toluene / 2.5 h / 20 - 35 °C
4.1: hydrogenchloride; acetic anhydride / tert-butyl methyl ether / 10 h / -5 - 30 °C
4.2: 5 h / Reflux
5.1: methanol / 6 h / Reflux
View Scheme
2-methyl-α-hydroxyiminobenzeneacetonitrile
107960-33-8

2-methyl-α-hydroxyiminobenzeneacetonitrile

methyl (E)-2-methoxyimino-2-[2-(o-tolyloxymethyl)phenyl]acetate
143390-89-0

methyl (E)-2-methoxyimino-2-[2-(o-tolyloxymethyl)phenyl]acetate

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: sodium hydroxide / water / 0.5 h / 11 - 15 °C
2.1: sodium hydroxide / water / 2.5 h / 50 - 65 °C
2.2: 25 °C
3.1: dibenzoyl peroxide; 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione / 1,2-dichloro-ethane / 4 h / 55 °C
4.1: copper(l) iodide / butanone / 4 h / Reflux
View Scheme
Multi-step reaction with 4 steps
1.1: sodium hydroxide / water / 0.5 h / 11 - 15 °C
2.1: sodium hydroxide / water / 3 h / 70 - 75 °C
2.2: 5 - 10 °C
3.1: dibenzoyl peroxide; 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione / 1,2-dichloro-ethane / 4 h / 55 °C
4.1: copper(l) iodide / butanone / 4 h / Reflux
View Scheme
Multi-step reaction with 4 steps
1.1: sodium hydroxide / water / 1 h / 7 - 15 °C
2.1: sodium hydroxide / water / 2.5 h / 50 - 65 °C
2.2: 25 °C
3.1: dibenzoyl peroxide; 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione / 1,2-dichloro-ethane / 4 h / 55 °C
4.1: copper(l) iodide / butanone / 4 h / Reflux
View Scheme
2-methyl-a-cyanobenzoxime potassium
178983-50-1

2-methyl-a-cyanobenzoxime potassium

methyl (E)-2-methoxyimino-2-[2-(o-tolyloxymethyl)phenyl]acetate
143390-89-0

methyl (E)-2-methoxyimino-2-[2-(o-tolyloxymethyl)phenyl]acetate

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: sodium hydroxide / water / 0.5 h / 8 - 10 °C
2.1: sodium hydroxide / water / 2.5 h / 50 - 65 °C
2.2: 25 °C
3.1: dibenzoyl peroxide; 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione / 1,2-dichloro-ethane / 4 h / 55 °C
4.1: copper(l) iodide / butanone / 4 h / Reflux
View Scheme
Multi-step reaction with 4 steps
1.1: sodium hydroxide / water / 0.5 h / 8 - 10 °C
2.1: sodium hydroxide / water / 3 h / 70 - 75 °C
2.2: 5 - 10 °C
3.1: dibenzoyl peroxide; 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione / 1,2-dichloro-ethane / 4 h / 55 °C
4.1: copper(l) iodide / butanone / 4 h / Reflux
View Scheme
Multi-step reaction with 4 steps
1.1: sodium hydroxide / water / 0.5 h / 8 - 10 °C
2.1: sodium carbonate / water / 1.6 h / 80 - 85 °C
2.2: 6 °C
3.1: dibenzoyl peroxide; 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione / 1,2-dichloro-ethane / 4 h / 55 °C
4.1: copper(l) iodide / butanone / 4 h / Reflux
View Scheme
2-methyl-a-cyanobenzoxime sodium

2-methyl-a-cyanobenzoxime sodium

methyl (E)-2-methoxyimino-2-[2-(o-tolyloxymethyl)phenyl]acetate
143390-89-0

methyl (E)-2-methoxyimino-2-[2-(o-tolyloxymethyl)phenyl]acetate

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: sodium hydroxide / water / 0.5 h / 8 - 10 °C
2.1: sodium hydroxide / water / 2.5 h / 50 - 65 °C
2.2: 25 °C
3.1: dibenzoyl peroxide; 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione / 1,2-dichloro-ethane / 4 h / 55 °C
4.1: copper(l) iodide / butanone / 4 h / Reflux
View Scheme
Multi-step reaction with 4 steps
1.1: sodium hydroxide / water / 0.5 h / 8 - 10 °C
2.1: sodium hydroxide / water / 3 h / 70 - 75 °C
2.2: 5 - 10 °C
3.1: dibenzoyl peroxide; 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione / 1,2-dichloro-ethane / 4 h / 55 °C
4.1: copper(l) iodide / butanone / 4 h / Reflux
View Scheme
Multi-step reaction with 4 steps
1.1: sodium hydroxide / water / 0.5 h / 8 - 10 °C
2.1: sodium carbonate / water / 1.6 h / 80 - 85 °C
2.2: 6 °C
3.1: dibenzoyl peroxide; 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione / 1,2-dichloro-ethane / 4 h / 55 °C
4.1: copper(l) iodide / butanone / 4 h / Reflux
View Scheme
2-benzofuran-1(3H)-one
87-41-2

2-benzofuran-1(3H)-one

methyl (E)-2-methoxyimino-2-[2-(o-tolyloxymethyl)phenyl]acetate
143390-89-0

methyl (E)-2-methoxyimino-2-[2-(o-tolyloxymethyl)phenyl]acetate

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: sodium methylate / methanol / 1 h / 20 °C
1.2: 2 h / 190 °C
2.1: thionyl chloride / 3 h / Reflux
3.1: tetrabutylammomium bromide / toluene / 2.5 h / 20 - 35 °C
4.1: hydrogenchloride; acetic anhydride / tert-butyl methyl ether / 10 h / -5 - 30 °C
4.2: 5 h / Reflux
5.1: methanol / 6 h / Reflux
View Scheme
2-tolylmethylnitrile
22364-68-7

2-tolylmethylnitrile

methyl (E)-2-methoxyimino-2-[2-(o-tolyloxymethyl)phenyl]acetate
143390-89-0

methyl (E)-2-methoxyimino-2-[2-(o-tolyloxymethyl)phenyl]acetate

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: ethyl nitrite; sodium hydroxide / chlorobenzene / 1 h / 15 °C
2.1: sodium hydroxide / water / 0.5 h / 8 - 10 °C
3.1: sodium carbonate / water / 1.6 h / 80 - 85 °C
3.2: 6 °C
4.1: dibenzoyl peroxide; 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione / 1,2-dichloro-ethane / 4 h / 55 °C
5.1: copper(l) iodide / butanone / 4 h / Reflux
View Scheme
Multi-step reaction with 5 steps
1.1: isopentyl nitrite; potassium hydroxide / chlorobenzene / 1 h / 15 °C
2.1: sodium hydroxide / water / 0.5 h / 8 - 10 °C
3.1: sodium carbonate / water / 1.6 h / 80 - 85 °C
3.2: 6 °C
4.1: dibenzoyl peroxide; 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione / 1,2-dichloro-ethane / 4 h / 55 °C
5.1: copper(l) iodide / butanone / 4 h / Reflux
View Scheme
Multi-step reaction with 5 steps
1.1: sodium carbonate; n-propyl nitrite / dichloromethane / 1.5 h / 5 °C
2.1: sodium hydroxide / water / 0.5 h / 11 - 15 °C
3.1: sodium hydroxide / water / 2.5 h / 50 - 65 °C
3.2: 25 °C
4.1: dibenzoyl peroxide; 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione / 1,2-dichloro-ethane / 4 h / 55 °C
5.1: copper(l) iodide / butanone / 4 h / Reflux
View Scheme
2-methyl-α-methoxyiminophenylacetonitrile

2-methyl-α-methoxyiminophenylacetonitrile

methyl (E)-2-methoxyimino-2-[2-(o-tolyloxymethyl)phenyl]acetate
143390-89-0

methyl (E)-2-methoxyimino-2-[2-(o-tolyloxymethyl)phenyl]acetate

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: sodium carbonate / water / 1.6 h / 80 - 85 °C
1.2: 6 °C
2.1: dibenzoyl peroxide; 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione / 1,2-dichloro-ethane / 4 h / 55 °C
3.1: copper(l) iodide / butanone / 4 h / Reflux
View Scheme
Multi-step reaction with 3 steps
1.1: sodium hydroxide / water / 2.5 h / 50 - 65 °C
1.2: 25 °C
2.1: dibenzoyl peroxide; 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione / 1,2-dichloro-ethane / 4 h / 55 °C
3.1: copper(l) iodide / butanone / 4 h / Reflux
View Scheme
Multi-step reaction with 3 steps
1.1: sodium hydroxide / water / 3 h / 70 - 75 °C
1.2: 5 - 10 °C
2.1: dibenzoyl peroxide; 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione / 1,2-dichloro-ethane / 4 h / 55 °C
3.1: copper(l) iodide / butanone / 4 h / Reflux
View Scheme
methyl-(E)-2-(2-tolyl)-2-methoxyiminoacetate
120974-97-2

methyl-(E)-2-(2-tolyl)-2-methoxyiminoacetate

methyl (E)-2-methoxyimino-2-[2-(o-tolyloxymethyl)phenyl]acetate
143390-89-0

methyl (E)-2-methoxyimino-2-[2-(o-tolyloxymethyl)phenyl]acetate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: dibenzoyl peroxide; 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione / 1,2-dichloro-ethane / 4 h / 55 °C
2: copper(l) iodide / butanone / 4 h / Reflux
View Scheme
methyl (E)-2-methoxyimino-2-[2-(o-tolyloxymethyl)phenyl]acetate
143390-89-0

methyl (E)-2-methoxyimino-2-[2-(o-tolyloxymethyl)phenyl]acetate

(E)-methyl 2-(2-((4-iodo-2-methylphenoxy)methyl)phenyl)-2-(methoxyimino)acetate

(E)-methyl 2-(2-((4-iodo-2-methylphenoxy)methyl)phenyl)-2-(methoxyimino)acetate

Conditions
ConditionsYield
With Iodine monochloride In dichloromethane; acetic acid at 20℃; for 5h;95%
methyl (E)-2-methoxyimino-2-[2-(o-tolyloxymethyl)phenyl]acetate
143390-89-0

methyl (E)-2-methoxyimino-2-[2-(o-tolyloxymethyl)phenyl]acetate

(E)-2-methoxyimino-2-{[2-(2-tolyl)oxymethyl]phenyl}acetic acid
1007364-30-8

(E)-2-methoxyimino-2-{[2-(2-tolyl)oxymethyl]phenyl}acetic acid

Conditions
ConditionsYield
Stage #1: methyl (E)-2-methoxyimino-2-[2-(o-tolyloxymethyl)phenyl]acetate With sodium hydroxide In water; toluene at 40 - 70℃; for 6h;
Stage #2: With hydrogenchloride In water; toluene at 10 - 15℃; pH=1.5;
93.75%
With water; sodium hydroxide In methanol for 3h; Reflux;92%
With sodium hydroxide In methanol at 65℃;86%
With sodium hydroxide; water In methanol Reflux;
methyl (E)-2-methoxyimino-2-[2-(o-tolyloxymethyl)phenyl]acetate
143390-89-0

methyl (E)-2-methoxyimino-2-[2-(o-tolyloxymethyl)phenyl]acetate

N-Methyl-E-2-methoxyimino-2-[(2-methylphenyloxymethyl)phenyl]-acetamide
156996-22-4

N-Methyl-E-2-methoxyimino-2-[(2-methylphenyloxymethyl)phenyl]-acetamide

Conditions
ConditionsYield
In methylamine
In methylamine
methyl (E)-2-methoxyimino-2-[2-(o-tolyloxymethyl)phenyl]acetate
143390-89-0

methyl (E)-2-methoxyimino-2-[2-(o-tolyloxymethyl)phenyl]acetate

(E)-tert-butyl 6-(4-((2-(2-methoxy-1-(methoxyimino)-2-oxoethyl)benzyl)oxy)-3-methylphenyl)hex-5-ynoate

(E)-tert-butyl 6-(4-((2-(2-methoxy-1-(methoxyimino)-2-oxoethyl)benzyl)oxy)-3-methylphenyl)hex-5-ynoate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: Iodine monochloride / dichloromethane; acetic acid / 5 h / 20 °C
2: copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride; triethylamine / N,N-dimethyl-formamide / 3 h / 20 °C / Inert atmosphere
View Scheme
methyl (E)-2-methoxyimino-2-[2-(o-tolyloxymethyl)phenyl]acetate
143390-89-0

methyl (E)-2-methoxyimino-2-[2-(o-tolyloxymethyl)phenyl]acetate

(E)-tert-butyl 6-(4-((2-(2-methoxy-1-(methoxyimino)-2-oxoethyl)benzyl)oxy)-3-methylphenyl)hexanoate

(E)-tert-butyl 6-(4-((2-(2-methoxy-1-(methoxyimino)-2-oxoethyl)benzyl)oxy)-3-methylphenyl)hexanoate

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: Iodine monochloride / dichloromethane; acetic acid / 5 h / 20 °C
2: copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride; triethylamine / N,N-dimethyl-formamide / 3 h / 20 °C / Inert atmosphere
3: Wilkinson's catalyst; hydrogen / tetrahydrofuran / 16 h / 20 °C / 3040.2 Torr
View Scheme
methyl (E)-2-methoxyimino-2-[2-(o-tolyloxymethyl)phenyl]acetate
143390-89-0

methyl (E)-2-methoxyimino-2-[2-(o-tolyloxymethyl)phenyl]acetate

(E)-6-(4-((2-(2-methoxy-1-(methoxyimino)-2-oxoethyl)benzyl)oxy)-3-methylphenyl)hexanoic acid

(E)-6-(4-((2-(2-methoxy-1-(methoxyimino)-2-oxoethyl)benzyl)oxy)-3-methylphenyl)hexanoic acid

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: Iodine monochloride / dichloromethane; acetic acid / 5 h / 20 °C
2: copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride; triethylamine / N,N-dimethyl-formamide / 3 h / 20 °C / Inert atmosphere
3: Wilkinson's catalyst; hydrogen / tetrahydrofuran / 16 h / 20 °C / 3040.2 Torr
4: formic acid / 3 h / 20 °C / Inert atmosphere
View Scheme
methyl (E)-2-methoxyimino-2-[2-(o-tolyloxymethyl)phenyl]acetate
143390-89-0

methyl (E)-2-methoxyimino-2-[2-(o-tolyloxymethyl)phenyl]acetate

(E)-tert-butyl 6-(2-(methoxyimino)-2-(2-((o-tolyloxy)methyl)phenyl)acetoxy)hexanoate

(E)-tert-butyl 6-(2-(methoxyimino)-2-(2-((o-tolyloxy)methyl)phenyl)acetoxy)hexanoate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: sodium hydroxide / methanol / 65 °C
2: potassium carbonate / N,N-dimethyl-formamide / 24 h / 20 °C / Inert atmosphere
View Scheme
methyl (E)-2-methoxyimino-2-[2-(o-tolyloxymethyl)phenyl]acetate
143390-89-0

methyl (E)-2-methoxyimino-2-[2-(o-tolyloxymethyl)phenyl]acetate

(E)-6-(2-(methoxyimino)-2-(2-((o-tolyloxy)methyl)phenyl)acetoxy)hexanoic acid

(E)-6-(2-(methoxyimino)-2-(2-((o-tolyloxy)methyl)phenyl)acetoxy)hexanoic acid

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: sodium hydroxide / methanol / 65 °C
2: potassium carbonate / N,N-dimethyl-formamide / 24 h / 20 °C / Inert atmosphere
3: formic acid / 3 h / 20 °C / Inert atmosphere
View Scheme
methyl (E)-2-methoxyimino-2-[2-(o-tolyloxymethyl)phenyl]acetate
143390-89-0

methyl (E)-2-methoxyimino-2-[2-(o-tolyloxymethyl)phenyl]acetate

C28H32N2O8

C28H32N2O8

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: Iodine monochloride / dichloromethane; acetic acid / 5 h / 20 °C
2: copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride; triethylamine / N,N-dimethyl-formamide / 3 h / 20 °C / Inert atmosphere
3: Wilkinson's catalyst; hydrogen / tetrahydrofuran / 16 h / 20 °C / 3040.2 Torr
4: formic acid / 3 h / 20 °C / Inert atmosphere
5: triethylamine / acetonitrile / 0 - 20 °C / Inert atmosphere
View Scheme
methyl (E)-2-methoxyimino-2-[2-(o-tolyloxymethyl)phenyl]acetate
143390-89-0

methyl (E)-2-methoxyimino-2-[2-(o-tolyloxymethyl)phenyl]acetate

C27H30N2O8

C27H30N2O8

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: sodium hydroxide / methanol / 65 °C
2: potassium carbonate / N,N-dimethyl-formamide / 24 h / 20 °C / Inert atmosphere
3: formic acid / 3 h / 20 °C / Inert atmosphere
4: triethylamine / acetonitrile / 0 - 20 °C / Inert atmosphere
View Scheme
methyl (E)-2-methoxyimino-2-[2-(o-tolyloxymethyl)phenyl]acetate
143390-89-0

methyl (E)-2-methoxyimino-2-[2-(o-tolyloxymethyl)phenyl]acetate

C23H28BrNO4

C23H28BrNO4

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: sodium hydroxide; water / methanol / 3 h / Reflux
2: dicyclohexyl-carbodiimide; dmap / dichloromethane / 12 h / 20 °C / Reflux
View Scheme
methyl (E)-2-methoxyimino-2-[2-(o-tolyloxymethyl)phenyl]acetate
143390-89-0

methyl (E)-2-methoxyimino-2-[2-(o-tolyloxymethyl)phenyl]acetate

C41H43NO4P(1+)*Br(1-)

C41H43NO4P(1+)*Br(1-)

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: sodium hydroxide; water / methanol / 3 h / Reflux
2: dicyclohexyl-carbodiimide; dmap / dichloromethane / 12 h / 20 °C / Reflux
3: potassium iodide / acetonitrile / 24 h / Reflux
View Scheme

143390-89-0Relevant articles and documents

Green synthetic method of kresoxim-methyl

-

, (2019/11/13)

The invention belongs to the technical field of fine chemical engineering, and particularly relates to a green synthetic method of kresoxim-methyl. The method comprises the following steps: carrying out nitrous nitrification by using 2-methylbenzyl cyanide as an initial raw material, carrying out methylation, carrying out hydrolytic methylation or hydrolytic esterification, carrying out bromination and carrying out an etherification reaction to obtain the high-content kresoxim-methyl. The method provided by the invention has a short reaction period, a high conversion rate, and excellent product quality, changes the defect that high-concentration hydrochloric acid gas is used for preparation in a traditional process, and has the advantages of simple operation steps, simple equipment, low energy consumption, a short period, high productivity and environmental protection.

FUNGICIDAL MIXTURES

-

, (2012/04/18)

The present invention relates to fungicidal mixtures comprising, as active components, 1) azolylmethyloxiranes of the general formula I wherein the variables have the meanings described in the application, 2) a fungicidal compound II, and 3) optionally a further fungicidal compound II, where the compounds II of components 2 and 3 independently of one another are selected from the group consisting of the compounds described in the application, with the proviso that components 2 and 3 are not identical, and to the use of the fungicidal mixtures for controlling phytopathogenic fungi and to the compositions comprising them.

IMPROVED PROCESS FOR PREPARING O-CHLOROMETHYLPHENYLGLYOXYLIC ESTERS, IMPROVED PROCESS FOR PREPARING (E)-2-(2-CHLOROMETHYLPHENYL)-2-ALKOXIMINOACETIC ESTERS, AND NOVEL INTERMEDIATES FOR THEIR PREPARATION

-

Page/Page column 13, (2008/12/08)

An improved process for preparing o-chloromethylphenylglyoxylic esters of the formula (I) which comprises converting a compound of the formula (II) by reaction with magnesium into the corresponding Grignard reagent which is then reacted with a compound of the formula (III) to give the compound of the formula (IV) which is then cleaved by reaction with a chloroformic ester of the formula ClCOOR4 or by reaction with phosgene to give the compound of the formula (I), followed by the isolation of the compound of the formula (I), and also an improved process for preparing (E)-2-(2-chloromethylphenyl)- 2-alkoximinoacetic esters of the formula (VII) and intermediates for their preparation.

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