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Literature

Origin of Trifluralin (treflam)

Tri+fluor+aniline
Trifluralin, a Group D dinitroanaline herbicide, was first introduced into the Australian cereal
market in the 1960s.Trifluralin was first registered in the United States in 1963 as a selective
preemergent herbicide.
In 1963 Dallyn and Sawyer reported that when this herbicide was applied to the soil surface prior
to transplanting tomato plants, it caused the formation of a corky abscission like layer in the
transplanted plants at the ground level.
In 1965, Standifer and Thomas have shown that when the herbicide is incorporated to various
depths lateral root information does not occur in cotton plants in the soil region, where the
herbicide is usually found. Kempen in 1965 noted the effect of treflam on weeds in cotton fields
stated that treflam controls weed primarily by preventing the development of thermal root
growth.In the same year HM Worth and R C Anderson worked on the toxicity of treflam, which
was an herbicide to mammals and chickens.
Treflam is a soil active compound and the best results are obtained when it is incorporated in to
the soil to depths of 2 to 4 inches as a preemergence control for annual weeds kempen (1965)
states that, miller and carter (workers at the shafter USDA cotton research station) have shown
that where treflam was mixed with the soil the lateral root system of cotton was inhibited. Its
ability to control grass weed populations, and the fact that alternatives did not exist, trifluralin
was adopted extensively. It remained the dominant grass herbicide in cereals throughout the
1960s and 1970s.
Trials were carried out on an alluvial meadow soil in 1966-67 by V Rankow and E Elenkov.
Treflan (trifluralin) at 0.4 and 1.8 kg a.i./ha, applied in May-June on plots with and without
French beans, stimulated soil microflora and increased the ammonifying, nitrifying and
cellulose-decomposing activities of the soil; the effect lasted about 6-7 weeks.Herbicide
inhibition of nodulation increased with varietal sensitivity but nodulation of the cvs. Logon,
Saxa, Wax Kwitlinga and Processor was increased 2.4-2.9 times 40 days after treatment with
trifluralin at 0.7 kg/ha. In 1966 The Effects of Treflan and Meloidogyne Hapla on the Growth of
Periwinkle (Vinca Major). LH Fuchigami from University of Minnesota, In 1967 MR Vega, JD
7

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Ona, FL Punzalan Evaluated of Herbicides for Weed Control in Lowland Rice,In 1967 Effect of
Incorporating Treflan with Four Common Tillage Tools was been studied by FE Edwards from
Mississippi State University,In 1970 Trials with Treflan in cabbage seed beds were done by PS
VASILENKO.
In 1972 TP Wu from Taiwania studied cytological effects of treflan and mitomycin C on root tips
of Vicia faba L.
In 1974 GN Tyunyaeva, AK Minenko, LA Pen'kov from Agrokhimiya studied the effect
of treflan on the bioloical properties of soil.
In 1975 DM Weatherspoon, WL Curre Evaluation of Treflan, Lasso and Ronstar herbicides
for use in woody ornamental nurseries.
In 1977 RL Cooper an Agronomy journal studied the Response of soybean cultivars to
narrow rows and planting rates under weed-free conditions.
In 1978 R Ross, J Morrison, DH Fine - Journal of agricultural and food, Assessed the
dipropylnitrosamine levels in a tomato field following application of Treflan EC.
In 1979 A Kabarity, A Nahas Induction of polyploidy and C-tumours after treatingAllium
cepa root tips with the herbicide Treflan. EPA initiated a Special Review of trifluralin in
August, 1979 because it was found to contain N-nitroso-di-n-propylamine (NDPA or
nitrosamine) at levels that met or exceeded the Agencys oncogenic risk criterion.
In the 1980s, a raft of new grass herbicides were introduced to the Australian winter cereal
market. They included diclofop-methyl (Hoegrass) and chlorosulfuron (Glean). Given the
post emergent activity of these products and high levels of efficacy achieved at that time,
they displaced much of the trifluralin market, and, a raft of new grass herbicides were
introduced to the Australian winter cereal market. They included diclofop-methyl (Hoegrass)
and chlorosulfuron (Glean). Given the post emergent activity of these products and high
levels of efficacy achieved at that time, they displaced much of the trifluralin market.
In 1982 RD Riggs, LR Oliver the Journal of Nematology studied the effect of trifluralin
(Treflan) on soybean cyst nematode. In concluding the Special Review in 1982, EPA required
registrants to achieve a 0.5 ppm upper limit for nitrosamines in their technical products. As
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part of the reregistration eligibility decision on trifluralin, the Agency is requiring that all
technical and manufacturing-use registrants submit nitrosamine analysis data to confirm that
levels remain at or below the 0.5 ppm limit
In 1985 SM Naqvi, VO Davis, RM Hawkins Percent mortalities and LC 50 values for
selected microcrustaceans exposed to treflan,and cutrine-plus herbicides.
In 1986 MA Pilinskaia from TSitologiia i genetika studied on Evaluation of the cytogenetic
effect of the herbicide treflan and of a number of its metabolites on mammalian somatic cells,
and J Altman a Phytopathologist studied the Enhancement Of Verticillium Wilt on
solananaceous vegetables by treflam.
A Registration Standard for trifluralin was issued in April 1987 and a Data Call-In for reentry protection data and mixer/loader/applicator exposure monitoring data for trifluralin
products used on turf was issued in March 1995.
Over reliance of these, and other highly selective Group A and Group B grass killers
throughout the 1980s and 1990s resulted in annual ryegrass populations developing
resistance to this chemistry. The industry now has largely turned back to trifluralin to
underpin ryegrass population control in winter cropping systems
In 1995 RU Khan, NA Khan, M Ahmad the Sarhad Journal of Agriculture worked on the
Performance of Treflan: a preplant applied herbicide in rapeseed and mustard.
In 1996 G Ribas, J Surralles, E Carbonell, N Xamena evaluated the herbicide treflam for
genotoxicity in cultured human peripheral blood lymphocytes. Sister-chromatid exchanges
(SCE), chromosome aberrations (CA) and micronuclei (MN) were scored as genetic
endpoints. To detect eventual metabolic modification in the genotoxicity of this herbicide, the
cultures for SCE and MN demonstration were also treated with S9 fraction. From our results
we can conclude that trifluralin was able to exert a weak cytotoxic effect, reducing both the
proliferative rate index (PRI) and the cytokinesis block proliferation index (CBPI), and also
to induce a slight but statistically significant increase in the frequency of SCE. Under our
conditions of testing, no genotoxic effects of trifluralin were observed in the CA and MN
assays.

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In 2000 In Sri Lanka, the active promotion of chemical products to prevent disease in shrimp
hatcheries has led to an increase in the use of drugs and chemicals without much emphasis on
understanding their efficacies. A survey was carried out to evaluate trends in the use of drugs
and chemicals as therapeutic treatments for shrimp-hatchery diseases. A wide range of
chemicals and drugs are being used, both for prophylactic treatment and to prevent or control
parasitic, fungal and bacterial diseases in hatcheries. Without proper scientific investigation
into treatment regimes, there has been a tendency for individual hatcheries to select their own
treatment regimens and to do their own experimentation. Little knowledge exists among
hatchery operators as to the hazardous effects of the chemicals in use. Lack of legislation on
the use of chemotherapeutants in aquaculture has led to the uncontrolled use and improper
selection of chemicals for use in shrimp hatcheries.
In 2001 NU Khan, SU Khan, G Hassan, IH Shah, Q Nawaz Studied on weed control in
cotton.
In 2002 RM Brand, C Mueller studied the Transdermal penetration of atrazine, alachlor, and
trifluralin: effect of formulation.
In 2003 S Hashim, KB Marwat, G Hassan studied the Chemical weed control efficiency in
potato (Solanum tuberosum L.) under agro-climatic conditions of Peshawar.
In 2004 CA Judge, JC Neal, JB Weber the JOURNAL OF ENVIRONMENTAL studied the
Dose and concentration responses of common nursery weeds to Gallery, Surflan andTreflan.
In 2005 MM Loux, D Doohan, AF Dobbels, WG Johnson wrote a book on the Weed control
guide for Ohio and Indiana.
In 2006 SA Uddin, MA Kade studied The use of treflam as antibiotics in shrimp hatcheries in
Bangladesh,and SH Lancaster, RL Haney, SA Sensema Journals of agricultural studied the
soil microbial activity is affected by Roundup WeatherMax and pesticides applied to cotton
In 2007 IA Khan, G Hassan, VM Salokhe studied the Chemical weeds control in canola.
In 2008 S Knen, T ava - Environmental and molecular mutagenesists worked on the
Genotoxicity testing of the herbicide trifluralin and its commercial formulation Treflan using
the piscine micronucleus test, IA Khan, G Hassan, KB Marwat, I Daur studied the Efficacy
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of some pre and post emergence herbicides on yield and yield components of canola in
2008.In 2010 SD Miller, JD Nalewaja studied the Fall preplant Treflan applications in
wheat.
In 2011 Field trial was conducted by IS Alsaadawi, A Khaliq, AA Al-Temimi, A Matloob in
brazil with the aim of utilizing allelopathic crop residues to reduce the use of
syntheticherbicides in broad bean (Vicia faba) fields. Sunflower residue at 600 and 1,400 g
m-2 and Treflan (trifluralin) at 50, 75 and 100% of recommended dose were incorporated into
the soil alone or in combination with each other. Untreated plots were maintained as a
control. Herbicide application in plots amended with sunflower residue had the least total
weed count and biomass, which was even better than herbicide used alone. Integration of
recommended dose of Treflan with sunflower residue at 1,400 g m- 2 produced maximum
(987.5 g m-2) aboveground biomass of broad bean, which was 74 and 36% higher than
control and recommended herbicide dose applied alone, respectively. Combination of
herbicide and sunflower residue appeared to better enhance pod number and yield per unit
area than herbicide alone. Application of 50% dose of Treflan in plots amended with
sunflower residue resulted in similar yield advantage as was noticed with 100% herbicide
dose. Chromatographic analysis of residue-infested field soil indicated the presence of
several phytotoxic compounds of phenolic nature. Periodic data revealed that maximum
suppression in weed density and dry weight synchronized with peak values of phytotoxins
observed 4 weeks after incorporation of sunflower residues. Integration of sunflower residues
with lower herbicide rates can produce effective weed suppression without compromising
yield as a feasible and environmentally sound approach in broad bean fields.
In

2012

Zohrabi,

A.; Naderidarbaghshahi,

M, Jalalizand

studied

on

the

Chemical weed control of autumnal rapeseed in Isfahan (Iran).

In 2013 S Komanduri studied the Effects of Treflan and Thiram and their interaction on
nodulation, nitrogen fixation, and yield of inoculated and uninoculated garden beans.
In 2014 SMH Nejad - Journal of Applied Science and Agriculture studied the Effect of
different tillage methods on the amounts of treflan upon parts productionand production
application seedling canola cultivar Hayola in the climatic conditions of DEZFUL Seyed
Mohammad Hashemi Nejad in iran ,and HR Miri, R Rastegar, B Jafari - International Journal
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of Biosciences studied the Separate and combined application of herbicide in bean weeds
control and its yield.

2.1 CHEMICAL REACTION:PCBT+HNO3

PCBNO2+H2O

PCBT+HNO3

PCBNO2+H2O

PCB(NO2)2 + NH(C3H7)2

C13H16F3N3O4 + HCL

2.2.CATALYST :

Sulfuric acid
Oleum

12