Dinitroanilines are a class of

chemical compound A chemical compound is a chemical substance composed of many identical molecules (or molecular entities) containing atoms from more than one chemical element held together by chemical bonds. A molecule consisting of atoms of only one element ...

s with the chemical formula C₆H₅N₃O₄. They are derived from both

aniline Aniline is an organic compound with the formula C6 H5 NH2. Consisting of a phenyl group attached to an amino group, aniline is the simplest aromatic amine In organic chemistry, an aromatic amine is an organic compound consisting of an aroma ...

and

dinitrobenzene Dinitrobenzenes are chemical compounds composed of a benzene ring and two nitro group (-NO2) substituents. The three possible arrangements of the nitro groups afford three isomers, 1,2-dinitrobenzene, 1,3-dinitrobenzene, and 1,4-dinitrobenzene. ...

s. There are six

isomer In chemistry, isomers are molecules or polyatomic ions with identical molecular formulae – that is, same number of atoms of each element – but distinct arrangements of atoms in space. Isomerism is existence or possibility of isomers. Iso ...

s: 2,3-dinitroaniline, 2,4-dinitroaniline, 2,5-dinitroaniline, 2,6-dinitroaniline, 3,4-dinitroaniline, and 3,5-dinitroaniline. Dinitroanilines are intermediates in the preparation of various industrially important chemicals including

dye A dye is a colored substance that chemically bonds to the substrate to which it is being applied. This distinguishes dyes from pigments which do not chemically bind to the material they color. Dye is generally applied in an aqueous solution an ...

s and

pesticide Pesticides are substances that are meant to control pests. This includes herbicide, insecticide, nematicide, molluscicide, piscicide, avicide, rodenticide, bactericide, insect repellent, animal repellent, microbicide, fungicide, and lampri ...

Herbicide Herbicides (, ), also commonly known as weedkillers, are substances used to control undesired plants, also known as weeds.EPA. February 201Pesticides Industry. Sales and Usage 2006 and 2007: Market Estimates. Summary in press releasMain page fo ...

s which are

derivatives The derivative of a function is the rate of change of the function's output relative to its input value. Derivative may also refer to: In mathematics and economics * Brzozowski derivative in the theory of formal languages * Formal derivative, an ...

of dinitroanilines include

benfluralin Benfluralin is an herbicide of the dinitroaniline class. The mechanism of action In pharmacology, the term mechanism of action (MOA) refers to the specific biochemical interaction through which a drug substance produces its pharmacological eff ...

, butralin, chlornidine, dinitramine, dipropalin, ethalfluralin, fluchloralin, isopropalin, methalpropalin, nitralin, oryzalin,

pendimethalin Pendimethalin is an herbicide of the dinitroaniline class p.328 used in premergence and postemergence applications to control annual grasses and certain broadleaf weeds. It inhibits cell division and cell elongation. Pendimethalin is listed in the ...

prodiamine Prodiamine is a preemergent herbicide of the dinitroaniline class. Prodiamine is used with crops such as soybeans, alfalfa, cotton, and ornamental crops. Prodiamine inhibits the formation of microtubules. Prodiamine was developed by Sandoz AG ...

, profluralin, and

trifluralin Trifluralin is a commonly used pre-emergence herbicide. With about used in the United States in 2001, it is one of the most widely used herbicides. Trifluralin is generally applied to the soil to provide control of a variety of annual grass an ...

. 2,4-Dinitroaniline can be prepared by reaction of

1-chloro-2,4-dinitrobenzene 2,4-Dinitrochlorobenzene (DNCB) is an organic compound with the chemical formula (O2N)2C6H3Cl. It is a yellow solid that is soluble in organic solvents. It is an important intermediate for the industrial production of other compounds. DNCB is p ...

with ammonia or by acid hydrolysis of 2,4-dinitroacetanilide. Dinitroanilines are explosive and flammable with heat or friction. Dinitroanilines were developed prior to 2015 by, among others, the

Dow Chemical Company The Dow Chemical Company, officially Dow Inc., is an American multinational chemical corporation headquartered in Midland, Michigan, United States. The company is among the three largest chemical producers in the world. Dow manufactures plastic ...

, who then sold their business to privately-held

Gowan Company Gowan may refer to: People *Charles Gowan (1850–1938) *David Gowan, American politician from Arizona *Franklin B. Gowen (1836–1889), attorney, president of Reading Railroad *Geoffrey Gowan (1929–2013), Canadian sports broadcaster *Hunter Go ...

.dowagro.com: "Gowan Company, L.L.C. Agrees to Acquire Global DNA Business from Dow AgroSciences LLC"
30 Nov 2015

References

{{Authority control Anilines Nitrobenzenes