Classifications

• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
  • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
  • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
  • C07D215/20—Oxygen atoms
  • C07D215/24—Oxygen atoms attached in position 8
  • C07D215/26—Alcohols; Ethers thereof
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
  • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
  • C07D215/04—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to the ring carbon atoms
  • C07D215/08—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to the ring carbon atoms with acylated ring nitrogen atom
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
  • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
  • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
  • C07D215/18—Halogen atoms or nitro radicals
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
  • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
  • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
  • C07D215/20—Oxygen atoms

Definitions

• This invention relates to new hydroquinolines useful as herbicides. More specifically, it relates to novel hydroquinolines wherein the nitrogen atom of the quinoline ring has an acyl substituent. While the preferred compounds of this invention are 1,2-dihydroquinolines, other dihydroquinolines, such as 3,4-dihydroquinolines, and more fully reduced derivatives, such as l,2,3,4-tetrahydroquinolines, are included.
• the compounds of this invention are represented by the following formulas:
• R is acyl having from 1 through 4 carbon atoms; R R and R are alkyl having from 1 through 4 carbon atoms; R, is hydrogen or alkyl having from 1 through 4 carbon atoms; R is hydrogen, halogen; alkyl or alkoxy having from 1 through 4 carbon atoms, or lower aromatic; and R is alkyl or alkoxy having from 1 through 4 carbon atoms, or monocyclic aromatic.
• the preferred compounds of this invention are those in which the acyl group on the l-position is halogenated with from 1 through 4 halogen atoms and R is hydrogen.
• the invention includes, however, many compounds with various other R entities; for example, ethoxy, tertbutyl, benzyloxy and chloro.
• the preferred compounds of this invention have chlorine substituents "ice in the acyl group and R is lower alkyl. 2,2,4',8-tetramethyl compounds are preferred because they are particularly elfective, and those in which R R and R or R are methyl are the most readily accessible.
• the new compounds of this invention are very effective pre-emergent herbicides; that is, they are most useful when applied to the soil after the crop seed is sown, but before the plants emerge. These compounds are particularly effective when it is desired to remove weed grasses from a broadleaf crop situs; this invention includes such a process.
• the present compounds can be formulated into their liquid or solid herbicidal composition and in [both forms a surface-active agent can be used to improve stability and facilitate application. They are soluble in a wide range of organic solvents, such as alcohols, ketones, hydrocarbons, halogenated hydrocarbons, and the like, and an appropriate non-ionic surface-active agent may be present in such solutions.
• the new compounds can also be suspended or emulsified in suitable liquid media, usually aqueous, and stabilization may be achieved with either ionic or non-ionic surface-active agents.
• suitable liquid media usually aqueous
• stabilization may be achieved with either ionic or non-ionic surface-active agents.
• Other conventional adjuvants can be employed in the formation of compositions of the present invention.
• the novel hydroquinolines can be used alone or in combination with other herbicides and pesticides.
• the concentration of the herbicide in the composition can vary widely and depends primarily on the intended use. For direct application, at least 1% by weight of composition is preferred, but amounts of about 10%, 25% or 50% by weight of composition can be used, particularly if subsequent dilution is intended.
• the amount of active ingredient applied per acre can be from about 2 to about 25 pounds, but the preferred application rate is from about 4 to about 6 pounds active compound per acre.
• acylation of a hydroquinoline analogous to the product desired, the preferred acylating agents being acyl halides, particularly the acyl chlorides, although acyl anhydrides can also be used.
• the acylation is preferably carried out in the presence of an acid acceptor, such as a tertiary amine, and most conveniently in the presence of an inert solvent, including hydrocarbons, halohydrocarbons, ethers and the like.
• the acylation can be carried out at temperatures from room temperature to about C.
• EXAMPLE 1 This example described the production of the new compound 1-chloroacetyl2,2,4,8-tetramethyl-1,2-dihydroquinoline.
• EXAMPLE 2 This example illustrates the herbicidal action of the product described in Example 1.
• R is a haloalkyl carbonyl the alkyl of which totals 1 through 3 carbon atoms said haloalkyl being substituted by from 1 to 3 like halogen atoms on at least one of the alpha and beta carbon atoms;
• R R and R are primary and secondary alkyl of 1 through 4 carbon atoms;
• R is hydrogen or primary or secondary alkyl of 1 through 4 carbon atoms;
• R is hydrogen, halogen, alkyl or alkoxy of 1 through 4 carbon atoms, phenyl or phenoxy,
• R is alkyl or alkoxy of 1 through 4 carbon atoms, phenyl, or phenoxy.
• R is chloroacetyl or dichloroacetyl.
• R is alkyl of 1 through 4 carbon atoms.
• the halogen of said haloalkyl carbonyl is chlorine.
• R is alkyl of from 1 through 4 carbon atoms.
• R R R and R are methyl, R is alkyl of 1 through 4 carbon atoms.

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• Chemical & Material Sciences (AREA)
• Organic Chemistry (AREA)
• Agricultural Chemicals And Associated Chemicals (AREA)
• Plural Heterocyclic Compounds (AREA)

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Citations (10)

• 0
  • GB GB1052308D patent/GB1052308A/en active Active
• 1968
  • 1968-03-27 US US739573*A patent/US3539578A/en not_active Expired - Lifetime

Patent Citations (10)

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