1918-02-1 Usage
Uses
Used in Agricultural Industry:
Picloram is used as a herbicide for controlling woody plants and a wide range of broad-leaved weeds along roads, power lines, and long right-of-ways. It is particularly useful in range management programs to control noxious weeds and brush, as well as in preparing sites for tree planting. It is available in various formulations, including as an acid (technical product), a potassium or triisopropanolamine salt, or an isooctyl ester, and can be found as soluble concentrates, pellets, or granular formulations.
Used in Non-cropland and Rights-of-way Management:
Picloram is used as a herbicide and defoliant in the management of unwanted vegetation in rangeland, grass pastures, forestry, and non-cropland. It is also used in rights-of-way sites, such as around industrial and military installations, roads, railways, airports, under power lines, and along pipelines. This application helps maintain clear and safe access to these areas.
Used in Combination with Other Herbicides:
Picloram is often used in combination with other herbicides such as 2,4-D or 2,4,5-T, bromoxynil, diuron, MCPA, triclorpyr, and atrazine to enhance its effectiveness in controlling a variety of annual weeds on crops, perennial broadleaved herbs, and woody species. It is also compatible with fertilizers, making it a versatile option for agricultural use.
Used in Specific Crops:
In some countries, Picloram is used in the cultivation of rice, sugarcane, cereals, and oilseed rape as a herbicide to control unwanted vegetation and promote the growth of the desired crop.
Air & Water Reactions
Insoluble in water.
Reactivity Profile
Picloram may be sensitive to prolonged exposure to light. Aqueous solutions may be decomposed by light. Picloram is incompatible with strong oxidizing agents, strong acids, acid chlorides and acid anhydrides.
Health Hazard
The toxic effects from ingestion or inhalation of dusts of picloram in test animals were mild. The acute oral LD50 values inrats and rabbits are 2900 and 2000 mg/kg,respectively. Maternal toxicity in rats wasobserved at a dose level of 750 mg/kg/day.Oral administration of picloram in rats andmice caused tumors in thyroid and liver.
Fire Hazard
Flash point data for Picloram are not available; however, Picloram is probably combustible.
Trade name
ACCESS?; AMDON?; AMDON GRAZON?; BOROLIN?; GRAZON? Picloram; K-PIN?; PATHWAY?; TORDON?[C]; TORDON? 101 MIXTURE; TORDON? 10 K; TORDON? 22 K
Biochem/physiol Actions
Picloram (4-Amino-3,5,6-trichloropyridine-2-carboxylic acid) is a chlorinated systemic herbicide widely used for woody plant and broad-leaved weed control. Picloram induces direct somatic embryogenesis of Lilium longiflorum var. Ceb-dazzel.
Safety Profile
Moderately toxic by
ingestion. Questionable carcinogen with
experimental carcinogenic, neoplas tigenic,
tumorigenic, and teratogenic data. An
experimental teratogen. Mutation data
reported. When heated to decomposition it
emits very toxic fumes of Cland NOx.
Potential Exposure
A potential danger to those involved in the manufacture, formulation or application of this herbicide.
Environmental Fate
Soil. Degrades in soil via cleavage of the chlorine atom at the m-position to form 4-
amino-5,6-dichloro-2-picolinic acid. Replacement of the chlorine at the m-posi-tion by a
hydroxyl group yields 4-amino-3-hydroxy-5,6-dichloropicolinic acid (Hartley and Kidd,
1987). Other soil metabolites reported include carbon dioxide, chloride ions, 4-amino-6-
hydroxy-3,5-dichloropicolinic acid (Meikle et al., 1974), 4-amino-3,5-dichloro-6-hydroxypicolinic acid and 4-amino-3,5,6-trichloropyridine (Goring and Hamaker, 1971). Youngson et al. (1967) reported that degradation increased with an increase in temperature and
organic matterThe half-lives for picloram in soil incubated in the laboratory under aerobic conditions
ranged from 29 days to 3 years with an average of 201 days (Meikle et al., 1973; Yoshida
and Castro, 1975; Merkle et al., 1976). In field soils, the half-lives for piGroundwater. According to the U.S. EPA (1986) picloram has a high potential to leach
to groundwater.Plant. Picloram degraded very slowly in cotton plants releasing carbon dioxide (Meikle
et al., 1966). Metabolites identified in spring wheat were 4-amino-2,3,5-trichloropyridine,
oxalic acid and 4-amino-3,5-dichloro-6-hydroxypicolinic acid (Redemann et al., 1968;
Plimmer, 1970). In soil, 4-amino-3,5-dichloro-6-hydroxypicolinic acid was the only compound positively identified (Redemann et al., 1968)Photolytic. The sodium salt of picloram in aqueous solution was readily decom-posed
by UV light (λ = 300–380 nm). Two chloride ions were formed for each molecule of
picloram that reacted. It was postulated that degradation proceeded via a free ra
Metabolism
Chemical. Picloram is generally stable to hydrolytic
degradation but will decompose in hot, concentrated
alkali solutions. It undergoes photodecomposition when
irradiated with UV light and, to a lesser extent,
with sunlight. Degradation via photolysis is thought to
primarily involve cleavage of the ring structure and
liberation of substituent chlorine atoms producing oxamic acid and 3-oxo-β-alanine. Decarboxylation is not thought
to be a major pathway in photolytic degradation.
Plant. Hall et al. (16) have shown that in rapeseed
plants (Brassica spp.) >25% of picloram is metabolized
24 hours after treatment.
Soil. There is only limited microbial degradation in the
soil. If picloram remains on the soil surface, it may undergo
photolysis.
Shipping
UN2588 Pesticides, solid, toxic, Hazard Class: 6.1; Labels: 6.1-Poisonous materials, Technical Name Required.
Toxicity evaluation
Mammalian Toxicity. Studies conducted on dog, rat,
steer, and human males indicate that most, if not
all, of orally administered picloram is quickly excreted
unmodified in the urine. The acute oral LD50s for male
rat, mice, rabbit, guinea pig, sheep, and cattle are >5000,
2000–4000, ca. 2000, ca. 3000, >1000, and >750 mg/kg,
respectively.
Weed Resistance/Modified Crop Tolerance. Weed resistance
to picloram has been reported in populations of
yellow starthistle (Centaurea solstitialis) (48) and wild
mustard (Sinapis arvensis) (34). No crops with modified
tolerance toward picloram are currently in production.
Incompatibilities
Incompatible with oxidizers (chlorates, nitrates, peroxides, permanganates, perchlorates, chlorine, bromine, fluorine, etc.); contact may cause fires or explosions. Keep away from alkaline materials, strong bases, strong acids, oxoacids, epoxides. Compounds of the carboxyl group react with all bases, both inorganic and organic (i.e., amines) releasing substantial heat, water and a salt that may be harmful. Incompatible with arsenic compounds (releases hydrogen cyanide gas), diazo compounds, dithiocarbamates, isocyanates, mercaptans, nitrides, and sulfides (releasing heat, toxic and possibly flammable gases), thiosulfates and dithionites (releasing hydrogen sulfate and oxides of sulfur). This material is acidic. Reacts with hot concentrated alkali (hydrolyzes), strong bases. May attack metals.
Waste Disposal
This chlorinated brush killer is usually formulated with 2,4-D and the disposal problems are similar. Incineration @ 1000C for 2 seconds is required for thermal decomposition. Alternatively, the free acid can be precipitated from its solutions by addition of a mineral acid. The concentrated acid can then be incinerated and the dilute residual solution disposed in an area where several years’ persistence in the soil can be tolerated.
Check Digit Verification of cas no
The CAS Registry Mumber 1918-02-1 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 1,9,1 and 8 respectively; the second part has 2 digits, 0 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 1918-02:
(6*1)+(5*9)+(4*1)+(3*8)+(2*0)+(1*2)=81
81 % 10 = 1
So 1918-02-1 is a valid CAS Registry Number.
InChI:InChI=1/C6H3Cl3N2O2/c7-1-3(10)2(8)5(9)11-4(1)6(12)13/h(H2,10,11)(H,12,13)
1918-02-1Relevant articles and documents
Electrophilic fluorination: the aminopyridine dilemma
Fields, Stephen C.,Lo, William C.,Brewster, William K.,Lowe, Christian T.
, p. 79 - 81 (2010)
An unusually high yielding fluorination of aminopyralid (3) using F-TEDA (SELECTFLUOR) in warm water, followed by kinetic resolution (via iterative esterification/saponification) of the crude fluorination product with dry HCl in methanol produced pure rin
NOXIOUS ARTHROPOD CONTROL AGENT CONTAINING AMIDE COMPOUND
-
, (2017/08/26)
An object of the present invention is to provide a compound having the controlling activity on a noxious arthropod, and a noxious arthropod controlling agent containing an amide compound of formula (I): wherein X represents a nitrogen atom or a CH group, p represents 0 or 1, A represents a tetrahydrofuranyl group or the like, R1, R2, R3, R4, R5, R6 and R7 represent a hydrogen atom or the like, n represents 1 or 2, Y represents an oxygen atom or the like, m represents any integer of 0 to 7, and Q represents a C1-8 chain hydrocarbon group optionally having a phenyl group or the like, has the excellent noxious arthropod controlling effect.
Design of protonated polyazamacrocycles based on phenanthroline motifs for selective uptake of aromatic carboxylate anions and herbicides
Cruz, Carla,Cahsto, Vania,Delgado, Rita,Felix, Vitor
supporting information; scheme or table, p. 3277 - 3289 (2009/12/05)
Three novel large polyazamacrocycles containing two 1,10-phenanthroline (phen) units connected by two polyamine spacers of different length, [32]phen2N4, [30]phen2N6 and Me 2[34]phen2N6, have been synthesised and their protonated forms used as receptors for binding studies with several aromatic carboxylate anions (benzoate (bzc-), 1-naphthalate (naphc -), 9-anthracenate (anthc-), pyrene-1-carboxyl-ate (pyrc-), phthalate, (ph2-), isophthalate (iph 2-), terephthalate (tph2-), 2,5-dihydroxy-1,4- benzenediacetate (dihyac2-) and, 1,3,5-benzenetricarboxylate (btc3-)) and three herbicides (4-amino-3,5,6-trichloropyridine-2- carbox-ylate (ATCP-), dichlorophenoxyacetate (2,4-D-) and glyphosate (PMG2-)) in water solution. The [30]phen2N 6 receptor was found to be the most suitable for binding the anions considered in a 1:1 stoichiometry. The three receptors exhibit a remarkable binding selectivity towards the extended aromatic anion pyre- at low pH values. Their binding affinities for the monocarboxylate anions decrease with the extension of the aromatic system in the order pyre- > anthc- > naphc- > bzc-, which indicates the presence of π-π stacking interactions in the molecular recognition of these anions. Molecular dynamics simulations carried out for the binding of (H4[30]phen2N6}4+ and {H 6Me2[34]phen2N6}6+ with pyre-, anthc-, naphc-, iph2- and btc3- in water showed that these receptors adopt a folded conformation with the anion inserted between the two phen heads and that the molecular recognition is governed by π-π stacking interactions and multiple N-H...O=C hydrogen bonds. The binding free energies estimated theoretically are very similar to those found by Potentiometric methods, which supports the proposed binding arrangement.
Methods for protecting ZEA mays plants against pest damage
-
, (2008/06/13)
According to the invention there is provided a method of controlling insect larvae comprising the steps of feeding said larvae an insecticidal amount of a transgenic Zea mays plant that expresses a polypeptide having the insect toxicity properties of Bacillus thuringiensis crystal protein.
Substituted pyridinesulfonamide compound or its salt, process for preparing the same, and herbicide containing the same
-
, (2008/06/13)
A substituted pyridinesulfonamide compound or its salt represented by the following general formula (I): STR1 wherein A is CH or N; when A is CH, R1 and R2 may be either each independently a member selected from the group consisting of unsubstituted or substituted alkyl groups, unsubstituted or substituted alkenyl groups, unsubstituted or substituted cycloalkyl groups, and unsubstituted or substituted phenyl groups; when A is N, R1 is an unsubstituted or substituted alkyl group, R2 is an unsubstituted or substituted alkyl group, or an unsubstituted or substituted alkoxy group; and X and Y are each independently a member selected from the group consisting of alkyl groups and alkoxy groups, is disclosed. This compound is useful as the effective ingredient of a herbicide showing a wide weed-control spectrum even if used in a small amount.
Herbicidal heterocyclic sulfonylurea compositions safened by herbicidal acids such as 2,4-D below a pH of 5
-
, (2008/06/13)
Disclosed are herbicidal concentrate formulation compositions having reduced grass crop plant phytotoxicity comprising certain sulfonamide or sulfonylurea herbicides in admixture with a herbicidal organic acid from the group consisting of clopyralid, 2,4-D, 2,4-DP, dicamba, dichlorprop-P, fluroxypyr MCPA, MCPP, mecoprop-P, picloram, triclopyr or mixtures of said acids; also disclosed is the preparation of said compositions and the pre- and post-emergent agricultural uses thereof in water diluted form.
Substituted pyridinesulfonamide compounds or their salts, process for preparing the same, and herbicides containing the same
-
, (2008/06/13)
A substituted pyridinesulfonamide compound or its salt represented by the following general formula (I): wherein R1 is an unsubstituted or substituted alkyl group; R2 is an unsubstituted or substituted alkyl group, or an unsubstituted or substituted alkoxy group; and X and Y are each independently a member selected from the group consisting of alkyl groups and alkoxy groups, is disclosed. This compound is useful as the effective ingredient of a herbicide showing a wide weed-control spectrum even if used in a small amount.
HYDROLYSIS OF 4-AMINO-3,5,6-TRICHLORO-2-TRICHLOROMETHYLPYRIDINE IN TRICHLOROACETIC ACID
Litvineneko, G. S.,Ovchinnikov, V. G.,Lobanova, I. A.,Maksimenko, N. M.,Zatsarevnyi, V. M.
, p. 824 - 830 (2007/10/02)
The hydrolysis of 4-amino-3,5,6-trichloro-2-trichloromethylpyridine in trichloroacetic acid, which gives approximately 80-90percent yields of 4-amino-3,5,6-trichloropicolinic acid and opens up the prospect of a marked reduction in the difficulty utilized sulfuric acid effluent formed during the normally employed hydrolysis in sulfuric acid, was investigated.The acid was isolated by diluting the hydrolysis mass with water, filtering off the precipitate, and regenerating the trichloroacetic acid by distillation of the water-acid mother solution or direct distillation of the trichloroacetic acid.Versions of the hydrolysis with repeated recycling of the trichloroacetic acid and sulfuric acid after distillation of the water from the mother solution without purification and also the hydrolysis of technical 4-amino-3,5,6-trichloro-2-trichloromethylpyridine are of technological interest.
Controlled release pesticides
-
, (2008/06/13)
Controlled release pesticide-polymers are prepared by reacting a polymer having a pendant group containing a reactive hydrogen with a chloroformamide derivative of a pesticide. In a preferred embodiment, metribuzin chloroformamide is prepared by reacting metribuzin with phosgene at a temperature of about 40° C. The metribuzin chloroformamide is then reacted with cellulose to form a pesticide-polymer from which the metribuzin is released under use conditions by hydrolytic degradation of the carbamate bond attaching the metribuzin to the polymer.
Preparation of 4-amino-3,5,6-trichloropicolinic acid
-
, (2008/06/13)
In a new method of producing 4-amino-3,5,6-trichloropicolinic acid 3,4,5,6-tetrachloropicolinonitrile is reacted with ammonium hydroxide, preferably at about 130° C. to about 160° C. The free acid is precipitated upon acidification of the reaction mixture and may be recovered therefrom.
