55335-06-3

Usage

Uses

Used in Agriculture:
Triclopyr is used as a systemic herbicide for controlling broadleaf weeds and woody plants in various agricultural settings. It is particularly effective when used on rice, range land, pasture, rights-of-way, forestry, and grasslands, including home lawns. Triclopyr is typically available in the form of a triclopyr butoxyethyl ester (BEE) or as a triclopyr triethylamine salt (TEA). Some products containing Triclopyr may be classified as Restricted Use Pesticides (RUP) due to their potential environmental impact.
Used in Regulatory Compliance:
Triclopyr is subject to maximum allowable residue levels in the U.S., as outlined in the Code of Federal Regulations (CFR). These regulations ensure that the herbicide and its metabolites, such as 3,5,6-trichloro-2-pyridinol and 2-methoxy-3,5,6-trichloropyridine, do not exceed specified limits in or on various raw agricultural commodities. For example, the maximum allowable residue levels for Triclopyr and its metabolites are as follows:
Fish: 3.0 ppm
Grass, forage, and hay: 500 ppm
Shellfish: 3.5 ppm
Egg: 0.05 ppm
Meat, fat, and meat byproducts (except kidney and liver) of cattle, goat, hog, horse, and sheep: 0.05 ppm
Meat, fat, and meat byproducts of poultry: 0.1 ppm
Milk: 0.01 ppm
Liver and kidney of cattle, goat, hog, horse, and sheep: 0.5 ppm
Rice, grain: 0.3 ppm
Rice, straw: 10.0 ppm
These regulations help maintain the safety and quality of agricultural products, ensuring that the use of Triclopyr as a herbicide does not pose significant risks to human health or the environment.

Trade name

[Note: See the following record, Triclopyr, triethylamine salt, for trade names containing the salt of triclopry] ACCESS?; CROSSBOW?, (triclopyr + 2,4-D ester); ET?; GARLON?; GRAZON? Triclopyr; PATHFINDER?; REDEEM?; RELY?; REMEDY?; RIVERDALE TAHOE? Nufarm (Australia); TURFLON?

Safety Profile

Moderately toxic by ingestion. Anexperimental teratogen. Experimental reproductiveeffects. Used as an herbicide. When heated todecomposition it emits toxic fumes of Clí and NOx.

Environmental Fate

Soil. In soil, triclopyr degraded to 3,5,6-trichloro-2-pyridinol and 2-methoxy-3,5,6- trichloropyridine (Norris et al., 1987). The major route of dissipation from soil is likely due to microbial degradation (Newton et al., 1990).Fifty-four days after triclopyr was applied to soil at a rate of 5.6 kg/ha, the majority (65%) remained in the top 10 cm of soil (Lee et al., 1986a).Ashton and Monaco (1991) reported triclopyr had an average half-life of 46 days and is in?uenced by soil type and climatic conditions.Plant. Lewer and Owen (1989) found 3,5,6-trichloro-2-pyridinol as the major metab- olite in plants. Cultured soybean cells metabolized triclopyr to dimethyl triclopyr-aspartate and dimethyl triclopyr-glutamate which can be rehydrolyzed to form the parent compound.At an application rate of 3.4 kg/ha, the dissipation half-life was 3.7 days. At an application rate of 3.3 kg/ka, the dissipation half-lives of triclopyr in brown, browse and litter samples were 73.5, 202.3 and 31 days, respectively (Norris et al., 1987).

Metabolic pathway

After 7 days in a soybean cell suspension culture, the major metabolites of trichlopyr are formed and identified as the aspartate (major) and glutamate (minor) amide conjugates.

Metabolism

The average half-life of triclopyr in soil is 46 days. Because triclopyr is sensitive to light, the length of time that it remains on the surface may moderate its persistence. Adsorption to soil is limited and is governed by the anion exchange capacity. Insignificant amounts are lost via volatilization. The propensity of triclopyr to translocate in the environment with soil water, is unknown.

Toxicity evaluation

The acute oral LD50 of triclopyr is 692 mg/kg and 577 mg/kg for male and female rat, respectively. It does not appear to undergo significant transformation and is excreted in the urine primarily unchanged.

InChI:InChI=1/C7H4Cl3NO3/c8-3-1-4(9)7(11-6(3)10)14-2-5(12)13/h1H,2H2,(H,12,13)

Upstream product

• 60825-27-6 ethyl 2-((3,5,6-trichloropyridin-2-yl)oxy)acetate 
• 60825-26-5 methyl 2-[(3,5,6-trichloropyridin-2-yl)oxy]acetate 
• 2402-79-1 2,3,5,6-tetrachloropyridine 
• 2921-88-2 Chlorpyrifos 
• 6515-38-4 3,5,6-trichloropyridin-2 ol 
• 79-11-8 chloroacetic acid 
• 623-73-4 diazoacetic acid ethyl ester 

Downstream Products

• 439680-85-0 methyl (S)-2-[[[(3,5,6-trichloro-2-pyridyl)oxy]methylcarbonyl]amino]-6-(2,4-dinitrophenyl)aminohexanoate 
• 64700-56-7 triclopyr butoxyethyl ester 

Relevant academic research and scientific papers

Monitoring of the organophosphate pesticide chlorpyrifos in vegetable samples from local markets in Northern Thailand by developed immunoassay

Chlorpyrifos is an organophosphate pesticide that is wildly used among farmers for crop protection. However, there are concerns regarding its contamination in the environment and food chain. In the present study, an in-house indirect competitive enzyme-linked immunosorbent assay (ic-ELISA) specific for detecting chlorpyrifos is developed and validated against gas chromatography–flame photometric detection (GC-FPD) as the conventional method. The developed ic-ELISA was used for detecting chlorpyrifos residue in vegetable samples. The developed ic-ELISA showed good sensitivity to chlorpyrifos at an IC50 of 0.80 μg/kg, with low cross-reactivity to other organophosphate pesticides. The 160 samples were collected from local markets located in the Chiang Rai, Chiang Mai, and Nan provinces in northern Thailand. The positive rate of chlorpyrifos residues in the vegetable samples was 33.8percent, with the highest levels found in cucumbers, coriander, and morning glory, at 275, 145, and 35.3 μg/kg, respectively. The highest median levels of chlorpyrifos found in the detected samples were Chinese cabbage (332 μg/kg), cucumber (146.3 μg/kg) and Chinese Kale (26.95 μg/kg). The developed ic-ELISA is suitable for the rapid quantitation of chlorpyrifos residues.

Synthesis and herbicidal activities of aryloxyacetic acid derivatives as HPPD inhibitors

A series of aryloxyacetic acid derivatives were designed and synthesized as 4-hydoxyphenylpyruvate dioxygenase (HPPD) inhibitors. Preliminary bioassay results reveal that these derivatives are promising Arabidopsis thaliana HPPD (AtHPPD) inhibitors, in particular compounds I12 (Ki = 0.011 μM) and I23 (Ki = 0.012 μM), which exhibit similar activities to that of mesotrione, a commercial HPPD herbicide (Ki = 0.013 μM). Furthermore, the newly synthesized compounds show significant greenhouse herbicidal activities against tested weeds at dosages of 150 g ai/ha. In particular, II4 exhibited high herbicidal activity for pre-emergence treatment that was slightly better than that of mesotrione. In addition, compound II4 was safe for weed control in maize fields at a rate of 150 g ai/ha, and was identified as the most potent candidate for a novel HPPD inhibitor herbicide. The compounds described herein may provide useful guidance for the design of new HPPD inhibiting herbicides and their modification.

NEW TYPE OF CYTIDINE DERIVATIVE AND APPLICATION THEREOF

The present disclosure provides a new cytidine derivative having the general formula (I), and applications thereof: R1 As demonstrated by experiments on the growth inhibition effect of the new cytidine derivative of the present invention on HCT-116 colon cancer xenografts in tumor-bearing nude mice , the compound of the present invention has high anti-tumor activity, data of impacts on weight of nude mice bearing human colon cancer HCT-116 and data of mortality rate showed that the toxicity of the compound is comparatively low.

Preparation method of herbicide triclopyr butoxyethyl ester

The invention discloses a preparation method of an herbicide, namely triclopyr butoxyethyl ester, belonging to the field of pesticide chemistry. The preparation method is implemented by the steps of reacting by virtue of raw materials including sodium trichloropyridinol and chloroacetic acid in the presence of a catalyst 1 and an organic solvent, so as to obtain picolinic acid type triclopyr (triklopir) as a raw material, preparing acyl chloride from triclopyr, carrying out condensation reaction by virtue of acyl chloride and 2-butoxyethanol in the presence of a catalyst 2, an acid-binding agent and an organic solvent, so as to obtain triclopyr butoxyethyl ester. The content of triclopyr butoxyethyl ester is 95.2%, and the yield is 85.6%; the synthesis is easy in operation, the post-treatment is simple and convenient, wastewater is little, and the preparation method is suitable for preparing the herbicide, namely triclopyr butoxyethyl ester.

3. 5, 6 - trichloro pyrrole oxygen acetic acid and its salt preparation method

The invention discloses a method for preparing 3, 5, 6-trichlopyr and a salt thereof. The method comprises the following steps: by taking trichloropyridine alkoxide as a raw material, under the condition of an alkaline environment and a catalyst, performing synthetic reaction with the chloroacetic acid alkali salt, further condensing by a solvent, cooling-crystallizing and separating to obtain 3, 5, 6-trichlopyr salt with percentage of more than 99.0%, carrying out oxidized decolouring and acidifying by an inorganic salt, and filtering and rinsing to obtain the 3, 5, 6-trichlopyr white crystal with percentage of more than 99.0%. Compared with the prior art, the method is synthesized by a one-step method and is simple in process; the solvent is recycled and the unit capacity wastewater discharge volume is greatly reduced; a high-quality, low-energy consumption and eco-environment-friendly production process for preparing 3, 5, 6-trichlopyr and the salt thereof is provided.

3, 5, 6-trichloro-2-pyridine phenoxyacetic acid derivatives preparation and applied research

The invention provides 3, 5, 6-trichlorine-2-pyridyloxyacetic acid derivatives which are soluble in both water and oil, have herbicidal activity and are shown as general formulas (I, II), wherein X refers to oxygen atoms, nitrogen atoms and sulfur atoms; n is 0, 1, 2, 3, 4, 5,..., or (CH2)n representing alkyl with a branched chain, wherein n refers to alkyl with a branched chain; Y refers to Cl-, Br-, F-, I-, AcO-, an acetylsalicylic acid radical, citric acid radical, salicylic acid radical, p-toluenesulfonic acid radical, hydrogen sulfate radical or other negative ions. R1 refers to alkyl with one to six carbon atoms, alkoxy with one to six carbon atoms, alkenyl with one to six carbon atoms, or aryl; R2 refers to alkyl with one to six carbon atoms, alkoxy with one to six carbon atoms, alkenyl with one to six carbon atoms or aryl groups; or R1 and R2 are selected from the structures shown in the specification.

Triclopyr production method

The invention provides a triclopyr production method. Firstly, sodium trichloropyrindinol and methyl chloroacetate have etherification reaction in a polar solvent to generate a midbody trichloropyridine peroxyacetic acid methyl ester, and trichloropyridine peroxyacetic acid methyl ester is subjected to alkaline hydrolysis and acidification in an aqueous phase to obtain triclopyr. When etherification reaction is conducted, reaction temperature is low, conditions are mild, reaction time is shortened, post-processing is simple, and the yield is high. A dispersing agent and a phase transfer catalyst are used during alkaline hydrolysis and acidification, alkaline hydrolysis and acidification are conducted in the aqueous phase, the amount of three wastes is reduced, reaction conditions are mild, the yield is high, production cost is low, industrial production is facilitated, and the yield of two-step reaction can reach 94% or above.

PREPARATION OF TRICLOPYR, ITS INTERMEDIATE AND BUTOXYETHYL ESTER

This invention relates to process for preparation of Triclopyr, Triclopyr- butoxyethyl ester and its intermediate viz. 2-butoxyethyl chloroacetate. Triclopyr is prepared by hydrolysis of its alkyl esters. Triclopyr- butoxyethyl ester is prepared by reaction of triclopyr and 2-butoxyethanol in presence of a catalyst. Triclopyr-butoxyethyl ester is also prepared by transesterification from alkyl esters of Triclopyr. 2-butoxyethyl chloroacetate is prepared by reaction of chloroacetic acid and 2-butoxyethanol in presence of a catalyst.

Fungicidal N-pyridyloxyalkyl amides

Compounds of the formula: STR1 wherein X is oxygen or sulfur; Z is oxygen or sulfur; R is pyridyl optionally substituted with 1 to 3 substituents independently selected from halogen, lower alkyl or lower alkoxy optionally substituted with 1 to 3 of the same or different halogen atoms or nitro; R1 is lower alkyl; and R2 is a 5- or 6-membered heterocyclic ring containing 1 to 3 ring nitrogens and the remainder of the ring atoms carbon atoms, a quinoline ring or a phenyl ring, all optionally substituted with 1 to 3 substituents independently selected from halogen, trihalomethyl, lower alkyl or lower alkoxy are fungicidal.

Fungicidal N-pyridyloxy alkyl amines

Compounds of the formula: STR1 wherein X is oxygen or sulfur; R is pyridyl optionally substituted with 1 to 3 substituents independently selected from halogen, lower alkyl or lower alkoxy optionally substituted with 1 to 3 of the same or different halogen atoms or nitro, R1 is lower alkyl; and R2 is a 5- or 6-membered heterocyclic ring containing 1- to 3-ring nitrogens and the remainder of the ring atoms carbon atoms, a quinoline ring or a phenyl ring, all optionally substituted with 1 to 3 substituents independently selected from halogen, trihalomethyl, lower alkyl or lower alkoxy, provided that R2 is not bonded to the --CH2 -- group by a ring nitrogen and compatible salts thereof, are fungicidal.