GB894435A - Herbicidal compositions - Google Patents

Herbicidal compositions

Info

Publication number
GB894435A
GB894435A GB2653659A GB2653659A GB894435A GB 894435 A GB894435 A GB 894435A GB 2653659 A GB2653659 A GB 2653659A GB 2653659 A GB2653659 A GB 2653659A GB 894435 A GB894435 A GB 894435A
Authority
GB
United Kingdom
Prior art keywords
acid
prepared
methoxy
treating
dichlorobenzoic
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired
Application number
GB2653659A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Velsicol Chemical Corp
Original Assignee
Velsicol Chemical Corp
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority to US753113A priority Critical patent/US3012870A/en
Priority to US760877A priority patent/US3012871A/en
Priority to US762237A priority patent/US3020146A/en
Priority to US76270958A priority
Priority to US76672058A priority
Priority to US76666458A priority
Priority to US76666258A priority
Priority to US766661A priority patent/US3012872A/en
Priority to US766663A priority patent/US3012873A/en
Priority to US77480658A priority
Priority to US77480758A priority
Application filed by Velsicol Chemical Corp filed Critical Velsicol Chemical Corp
Publication of GB894435A publication Critical patent/GB894435A/en
Expired legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C65/00Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C65/01Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing hydroxy or O-metal groups
    • C07C65/03Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing hydroxy or O-metal groups monocyclic and having all hydroxy or O-metal groups bound to the ring
    • C07C65/05Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing hydroxy or O-metal groups monocyclic and having all hydroxy or O-metal groups bound to the ring o-Hydroxy carboxylic acids
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C205/00Compounds containing nitro groups bound to a carbon skeleton
    • C07C205/49Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups
    • C07C205/56Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups having nitro groups bound to carbon atoms of six-membered aromatic rings and carboxyl groups bound to acyclic carbon atoms of the carbon skeleton
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C205/00Compounds containing nitro groups bound to a carbon skeleton
    • C07C205/49Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups
    • C07C205/57Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups having nitro groups and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
    • C07C205/59Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups having nitro groups and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton the carbon skeleton being further substituted by singly-bound oxygen atoms
    • C07C205/60Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups having nitro groups and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton the carbon skeleton being further substituted by singly-bound oxygen atoms in ortho-position to the carboxyl group, e.g. nitro-salicylic acids
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C57/00Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
    • C07C57/52Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing halogen
    • C07C57/58Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing halogen containing six-membered aromatic rings
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C59/00Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C59/40Unsaturated compounds
    • C07C59/58Unsaturated compounds containing ether groups, groups, groups, or groups
    • C07C59/64Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C65/00Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C65/21Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing ether groups, groups, groups, or groups

Abstract

2-methoxy-3,5-dichlorobenzoic acid is prepared by treating salicylic acid with gaseous chlorine in acetic acid solution at a temperature below 35 DEG C., dissolving the resulting 3,5-dichlorosalicyclic acid in aqueous sodium hydroxide and refluxing with dimethyl sulphate, adding further sodium hydroxide, refluxing and then acidifying the product. 2-methoxy-3.5-dibromobenzoic acid is prepared by treating the salicyclic acid with hydrogen bromide instead of chlorine in the above process. a -chlorophenylacetic acid is prepared (a) by heating mandelic acid to 140 DEG C. with concentrated hydrochloric acid (b) by the action of potassium hydroxide on trichloromethylphenylcarbinol (c) by the chlorination of phenylacetic acid and (d) by the action of water on the acid chloride obtained from mandelic acid and phosphorus pentachloride. a -chlorophenylacetic acid is converted to a ,a -dichlorophenylacetic acid by treating the melted monochloro compound with gaseous chlorine, preferably under illumination from actinic light. 2,6-dimethoxy-3-chlorobenzoic acid is prepared by treating 2,6-dihydroxyacetophenone in aqueous sodium hydroxide with dimethyl sulphate made basic to give 2,6-dimethoxyacetophenone, which is then heated with sodium hypochlorite and acidified. 2-amino-3,5-dichlorobenzoic acid is prepared by treating 3,5-dichlorobenzoic with fuming nitric acid, the 2-nitro-3,5-dichlorobenzoic acid produced is dissolved in ammonium hydroxide, refluxed with aqueous ferrous sulphate and acidified. 2,6-dichloro-3-methoxybenzoic acid is obtained by treating 2,6-dichloro-3-hydroxy-benzaldehyde in aqueous sodium bicarbonate with dimethyl sulphate, the methyl ether produced is refluxed with aqueous potassium permangenate containing sodium bicarbonate, treated with sodium bisulphite and acidified. 2-chloro-5-methoxybenzoic acid is similarly prepared from 2-chloro-5-hydroxybenzaldehyde. 2-Methoxy-3,5-dinitrobenzoic acid is prepared by cooling 2-methoxybenzoic acid with concentrated sulphuric acid to 25 DEG C. and adding concentrated nitric acid. 2-methoxy-3-methyl-5-chlorobenzoic acid is prepared by treating 3-methyl-5-chlorosalicyclic acid in aqueous sodium hydroxide with dimethyl sulphate. 2-amino-3,5,6-trichlorobenzoic acid is prepared by treating 3,4,6-trichlorophthalimide with sodium hypochlorite or by oxidising 4,5,7-trichloroisatin with hydrogen peroxide in a basic medium. The anhydride of 3-methoxy-2,6-dichlorobenzoic acid is prepared by dissolving the acid chloride of 3-methoxy-2,6-dichlorobenzoic acid in a mixture of pyridine and benzene and adding the free acid thereto, the acid chloride being prepared by the action of phosphorus trichloride on the free acid. The sodium salt of 2-methoxy-3,5-dichlorobenzoic acid is prepared by treating the free acid with sodium hydroxide in methanol solution and the butyl ester of the free acid is obtained by refluxing the free acid with butyl alcohol in benzene in the presence of p-toluenesulphonic acid. The diethanolamine salt of 2,6-dimethoxy-3-chlorobenzoic acid is obtained by treating the free acid in dry ether with diethanolamine and the N,N-diethylamide of the free acid is prepared by treating the acid chloride of 2,6-dimethoxy-3-chlorobenzoic acid with diethylamine in benzene solution. The amide of 3-methoxy-2,6-dichlorobenzoic acid is obtained by treating the acid chloride of the free acid with dry ammonia gas in benzene solution. The anhydrides, salts, esters and amides of the other chlorinated benzioc acids and phenyl acetic acids specified may be similarly prepared.ALSO:A herbicidal composition comprises a solid carrier or a surface-active agent or a solid or liquid carrier and a surface-active agent and one of the following compounds as active ingredient: 2 - methoxy - 3,5 - dichlorobenzoic acid, 2 - methoxy - 3,5 - dibromobenzoic acid, alpha - chlorophenylacetic acid, alpha-alpha-dichloro-phenylacetic acid, 2-amino-3,5-dichlorobenzoic acid, 2,6 - dimethoxy - 3 - chlorobenzoic acid, 2 - methoxy - 3,5 - dinitrobenzoic acid, 3 - methoxy - 2,6 - dichlorobenzoic acid, 2 - chloro - 5 - methoxybenzoic acid, 2 - methoxy - 3 - methyl - 5-chlorobenzoic acid and 2 - amino - 3,5,6, - trichlorobenzoic acid. The compound may be in the form of the free acid, the acid anhydride, a salt, an amide or an ester. The amide may be a substituted amide, e.g. the N-methyl, N-butyl, N-decyl, N,N-diethyl amide or an anilide and the N-alkyl group preferably contains 1 to 10 carbon atoms. The composition may be formulated as a dust containing 5 to 25% of the active ingredient in the form of its alkali metal or ammonium salt using talcs or clays as carriers, or as a spray in an organic solvent, e.g. Xylene, kerosene, methylated naphthalenes or methanol containing a surface-active agent as an ester or as an amine salt in aqueous solution containing a surface-active agent, e.g. the diethylamine, triethylamine, diethanolamine, triethanolamine, isopropylamine and morpholine salts. The active ingredients may also be emulsified or suspended in water. If desired, pesticides, stabilizers, activators, synergists, spreaders and adhesives may be added to the composition.
GB2653659A 1958-08-04 1959-08-04 Herbicidal compositions Expired GB894435A (en)

Priority Applications (11)

Application Number Priority Date Filing Date Title
US753113A US3012870A (en) 1958-08-04 1958-08-04 Method of destroying undesirable vegetation
US760877A US3012871A (en) 1958-09-15 1958-09-15 Method of destroying undesirable vegetation
US762237A US3020146A (en) 1958-09-22 1958-09-22 Method of destroying undesirable plants
US76270958A true 1958-09-23 1958-09-23
US76666458A true 1958-10-13 1958-10-13
US76672058A true 1958-10-13 1958-10-13
US76666258A true 1958-10-13 1958-10-13
US766661A US3012872A (en) 1958-10-13 1958-10-13 Method of destroying undesirable vegetation
US766663A US3012873A (en) 1958-10-13 1958-10-13 Method of destroying undesirable plant growth
US77480758A true 1958-11-19 1958-11-19
US77480658A true 1958-11-19 1958-11-19

Publications (1)

Publication Number Publication Date
GB894435A true GB894435A (en) 1962-04-18

Family

ID=27582809

Family Applications (1)

Application Number Title Priority Date Filing Date
GB2653659A Expired GB894435A (en) 1958-08-04 1959-08-04 Herbicidal compositions

Country Status (6)

Country Link
CH (1) CH408526A (en)
FR (1) FR1240716A (en)
GB (1) GB894435A (en)
LU (1) LU37508A1 (en)
NL (1) NL241974A (en)
SE (1) SE300724B (en)

Also Published As

Publication number Publication date
FR1240716A (en) 1960-09-09
SE300724B (en) 1968-05-06
CH408526A (en) 1966-02-28
LU37508A (en)
LU37508A1 (en)
NL241974A (en)

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