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99% Trifluralin CAS:1582-09-8
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1582-09-8 Usage

Agricultural Uses

Herbicide: Trifluralin is a selective, pre-emergence herbicide used to control many annual grasses and broadleaf weeds in a large variety of tree fruit, nut, vegetable, and grain crops, including soybeans, sunflowers, cotton, and alfalfa. It is also used on rights-of-way, on set-aside land (i.e., arable land temporarily taken out of use). A general use pesticide (GUP). Not approved for use in EU countries . Registered for use in the U.S.

Uses

Pre-emergence herbicide used for grass control in crops.

Fire Hazard

Special Hazards of Combustion Products: Toxic and irritating hydrogen fluoride gas may be formed in fires.

General Description

Yellow-orange crystalline solid. Denser than water and not soluble in water. Hence sinks in water. Melting point 48.5-49°C. Used as a selective pre emergence herbicide.

Trade name

AGREFLAN®; AGRIFLAN® 24; ASHLADE TRIMARAN®; AUTUMN KITE®; BROADSTRIKE®; BUCKLE®; CALLIFORT®; CAMPBELL'S TRIFLURON®; CHANDOR®; COMMENCE®; CRISALIN®; DEVRINOL T®; DIGERMIN®; ELANCOLAN®; FLINT®; FLORA®; FLURENE SE®; FLUTRIX®; FREEDOM®; GORDON’S WEEDER®; HERBIFLURIN®; IPERSAN®; JANUS®; L-36352®; LILLY 36,352®; LINNET®; MARKSMAN®; MARKSMAN 2, TRIGARD®; M. T. F®; NITRAN®; OLITREF®; ONSLAUGHT®; PREMERLIN 600 CE®; SINFLOWAN®; SOLO®; SU SEGURO CARPIDOR®; TEAM®; TREFANOCIDE®; TREFICON®; TREFLAN®; TREFLANOCIDE®; TRIFARMON®; TRIFLURALINA® 600; TRIFLUREX®; TRIFUREX®; TRIGARD®; TRIKEPIN®; TRILIN®; TRILIN® 10G; TRIM®; TRIMARAN®; TRIPART TRIFLURALIN 48 EC; TRISTAR®; TRUST®; TURFLAN®; URANUS® (trifluralin + linuron)

Definition

ChEBI: A substituted aniline that is N,N-dipropylaniline substituted by a nitro groups at positions 2 and 6 and a trifluoromethyl group at position 4. It is an agrochemical used as a pre-emergence herbicide.

Health Hazard

Dust may irritate eyes. No toxic symptoms have been observed during the manufacture and use of Trifluralin.

Description

Trifuralin (sold under trademe such as Treflan, Elancolan or Trefanocide) is a selective pre-emergence herbicide. It is used for pre-plant soil incorporation for the control against annual grasses and some broadleaf annual weeds. It is widely used on soybeans and cotton. It also finds its use in a large number of food crops, including broccoli, cabbage, onions, leafy green vegetables, beans, tomatoes, potatoes, wheat, sugar beet, and sugar cane. For its use on fruit trees, the plant must not be bearing fruit at the time of application. It may also be used to protect residential ornamental plants, such as trees, herbaceous plants, woody shrubs, and vines.
Trifluralin has low water solubility. It has high affinity for soil and is relatively immobile. It is not acutely toxic mammals, but it is highly toxic to fish and other aquatic organisms.

Reactivity Profile

Trifluralin is a trifluoromethyl dinitroaniline derivative. Dinitroaniline has a record of industrial explosions. Nothing has been reported implicating Trifluralin in any such accidents. This may be because of the trifluoromethyl substitution may mitigate the instability of the molecule. However, care should be taken in the extremes of heat, shock, and friction sources that may trigger an explosive release of energy.

References

  1. https://www.epa.gov
  2. http://www.toxipedia.org
  3. https://pubchem.ncbi.nlm.nih.gov
  4. http://www.who.int
  5. https://aggie-horticulture.tamu.edu
InChI:InChI=1/C13H16F3N3O4/c1-3-5-17(6-4-2)12-10(18(20)21)7-9(13(14,15)16)8-11(12)19(22)23/h7-8H,3-6H2,1-2H3

1582-09-8SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 15, 2017

Revision Date: Aug 15, 2017

1.Identification

1.1 GHS Product identifier

Product name trifluralin

1.2 Other means of identification

Product number -
Other names 2,6-Dinitro-N,N-dipropyl-4-trifluoromethylaniline

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:1582-09-8 SDS

1582-09-8Synthetic route

C13H17F3N3O5(1-)
72283-22-8

C13H17F3N3O5(1-)

2,6-dinitro-N,N-dipropyl-4-(trifluoromethyl)benzeneamine
1582-09-8

2,6-dinitro-N,N-dipropyl-4-(trifluoromethyl)benzeneamine

Conditions
ConditionsYield
With potassium hydroxide In water; dimethyl sulfoxide at 25℃; Equilibrium constant; Rate constant; var. of solvent mixture, var. KOH concentrations;
C17H26F3N4O4(1-)*K(1+)
79871-51-5

C17H26F3N4O4(1-)*K(1+)

A

2,6-dinitro-N,N-dipropyl-4-(trifluoromethyl)benzeneamine
1582-09-8

2,6-dinitro-N,N-dipropyl-4-(trifluoromethyl)benzeneamine

B

N-butylamine
109-73-9

N-butylamine

Conditions
ConditionsYield
With water In dimethyl sulfoxide Equilibrium constant;
C18H26F3N4O4(1-)*K(1+)
79816-19-6

C18H26F3N4O4(1-)*K(1+)

A

piperidine
110-89-4

piperidine

B

2,6-dinitro-N,N-dipropyl-4-(trifluoromethyl)benzeneamine
1582-09-8

2,6-dinitro-N,N-dipropyl-4-(trifluoromethyl)benzeneamine

Conditions
ConditionsYield
With water In dimethyl sulfoxide Equilibrium constant;
4-chloro-3,5-dinitrobenzotrifluoride
393-75-9

4-chloro-3,5-dinitrobenzotrifluoride

2,6-dinitro-N,N-dipropyl-4-(trifluoromethyl)benzeneamine
1582-09-8

2,6-dinitro-N,N-dipropyl-4-(trifluoromethyl)benzeneamine

Conditions
ConditionsYield
In water
4-chloro-3,5-dinitrobenzotrifluoride
393-75-9

4-chloro-3,5-dinitrobenzotrifluoride

di-n-propylamine
142-84-7

di-n-propylamine

2,6-dinitro-N,N-dipropyl-4-(trifluoromethyl)benzeneamine
1582-09-8

2,6-dinitro-N,N-dipropyl-4-(trifluoromethyl)benzeneamine

Conditions
ConditionsYield
Reflux;
With water; sodium hydroxide at 85 - 90℃; for 5h; Large scale;
With sodium hydroxide; ascorbic acid In water at 60℃; for 2h; pH=7.5 - 8.5; Temperature;33.02 g
piperidine
110-89-4

piperidine

2,6-dinitro-N,N-dipropyl-4-(trifluoromethyl)benzeneamine
1582-09-8

2,6-dinitro-N,N-dipropyl-4-(trifluoromethyl)benzeneamine

C18H26F3N4O4(1-)*K(1+)
79816-19-6

C18H26F3N4O4(1-)*K(1+)

Conditions
ConditionsYield
With potassium hydroxide In water; dimethyl sulfoxide Equilibrium constant;
2,6-dinitro-N,N-dipropyl-4-(trifluoromethyl)benzeneamine
1582-09-8

2,6-dinitro-N,N-dipropyl-4-(trifluoromethyl)benzeneamine

C13H17F3N3O5(1-)
72283-22-8

C13H17F3N3O5(1-)

Conditions
ConditionsYield
With potassium hydroxide In water; dimethyl sulfoxide at 25℃; Equilibrium constant; Rate constant; var.of solvent mixture, var. KOH concentrations;
2,6-dinitro-N,N-dipropyl-4-(trifluoromethyl)benzeneamine
1582-09-8

2,6-dinitro-N,N-dipropyl-4-(trifluoromethyl)benzeneamine

N-butylamine
109-73-9

N-butylamine

C17H26F3N4O4(1-)*K(1+)
79871-51-5

C17H26F3N4O4(1-)*K(1+)

Conditions
ConditionsYield
With potassium hydroxide In water; dimethyl sulfoxide at 25℃; Rate constant; Equilibrium constant;
2,6-dinitro-N,N-dipropyl-4-(trifluoromethyl)benzeneamine
1582-09-8

2,6-dinitro-N,N-dipropyl-4-(trifluoromethyl)benzeneamine

1-Dipropylamino-2,6-dinitro-4-tribrommethyl-benzol
16766-93-1

1-Dipropylamino-2,6-dinitro-4-tribrommethyl-benzol

Conditions
ConditionsYield
With aluminum tri-bromide
2,6-dinitro-N,N-dipropyl-4-(trifluoromethyl)benzeneamine
1582-09-8

2,6-dinitro-N,N-dipropyl-4-(trifluoromethyl)benzeneamine

A

3-nitro-5-trifluoromethyl-1,2-phenylenediamine
2078-01-5

3-nitro-5-trifluoromethyl-1,2-phenylenediamine

B

2,6-dinitro-4-trifluoromethylaniline
445-66-9

2,6-dinitro-4-trifluoromethylaniline

C

α,α,α-trifluoro-5-nitro-N4-propyltoluene-3,4-diamine
2078-02-6

α,α,α-trifluoro-5-nitro-N4-propyltoluene-3,4-diamine

D

α,α,α-trifluoro-2,6-dinitro-N-propyl-p-toluidine
2077-99-8

α,α,α-trifluoro-2,6-dinitro-N-propyl-p-toluidine

E

2,6-dinitro-4-trifluoromethyl-2',6'-dinitro-4'-<(trifluoromethyl)azo>benzene
69145-34-2

2,6-dinitro-4-trifluoromethyl-2',6'-dinitro-4'-<(trifluoromethyl)azo>benzene

F

2-ethyl-7-nitro-5-(trifluoromethyl)-1H-benzimidazole
51026-15-4

2-ethyl-7-nitro-5-(trifluoromethyl)-1H-benzimidazole

Conditions
ConditionsYield
In methanol; water Mechanism; Irradiation;
2,6-dinitro-N,N-dipropyl-4-(trifluoromethyl)benzeneamine
1582-09-8

2,6-dinitro-N,N-dipropyl-4-(trifluoromethyl)benzeneamine

A

di-n-propylamine
142-84-7

di-n-propylamine

B

C7H2N2O7(2-)*2K(1+)

C7H2N2O7(2-)*2K(1+)

C

potassium; 2,6-dinitro-4-trifluoromethyl-phenolate

potassium; 2,6-dinitro-4-trifluoromethyl-phenolate

D

C13H16(2)HF3N3O5(1-)*K(1+)

C13H16(2)HF3N3O5(1-)*K(1+)

E

C19H30F3N4O4(1-)*K(1+)

C19H30F3N4O4(1-)*K(1+)

Conditions
ConditionsYield
With potassium deuteroxide In dimethylsulfoxide-d6; water-d2 Mechanism; other dinitroaniline herbicides; other nucleophiles;
2,6-dinitro-N,N-dipropyl-4-(trifluoromethyl)benzeneamine
1582-09-8

2,6-dinitro-N,N-dipropyl-4-(trifluoromethyl)benzeneamine

trifluralin-d2

trifluralin-d2

Conditions
ConditionsYield
With deuteriated sodium hydroxide In dimethylsulfoxide-d6; water-d2 for 24h;
2,6-dinitro-N,N-dipropyl-4-(trifluoromethyl)benzeneamine
1582-09-8

2,6-dinitro-N,N-dipropyl-4-(trifluoromethyl)benzeneamine

α,α,α-Trifluoro-2,6-dinitro-p-cresol
393-77-1

α,α,α-Trifluoro-2,6-dinitro-p-cresol

Conditions
ConditionsYield
With sodium hydroxide; water In 1,4-dioxane for 18h; Heating;
2,6-dinitro-N,N-dipropyl-4-(trifluoromethyl)benzeneamine
1582-09-8

2,6-dinitro-N,N-dipropyl-4-(trifluoromethyl)benzeneamine

α,α,α-trifluoro-2,6-diamino-N,N-dipropyl-p-toluidine
2078-06-0

α,α,α-trifluoro-2,6-diamino-N,N-dipropyl-p-toluidine

Conditions
ConditionsYield
With iron In methanol
With zero-valent iron nanoparticles with palladium In methanol
With sodium tetrahydroborate In water for 0.333333h; Reagent/catalyst;
With sodium tetrahydroborate In ethanol; water at 30℃; for 0.416667h;
2,6-dinitro-N,N-dipropyl-4-(trifluoromethyl)benzeneamine
1582-09-8

2,6-dinitro-N,N-dipropyl-4-(trifluoromethyl)benzeneamine

A

2-ethyl-4-nitro-6-(trifluoromethyl)-1H-benzimidazole
51026-15-4

2-ethyl-4-nitro-6-(trifluoromethyl)-1H-benzimidazole

B

α,α,α-trifluoro-2,6-dinitro-N-propyl-p-toluidine
2077-99-8

α,α,α-trifluoro-2,6-dinitro-N-propyl-p-toluidine

Conditions
ConditionsYield
With 2,3-Dimethyl-2-butene; ozone Kinetics;

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