Thompson, H. E.; Swanson, Carl P.; Norman, A. G. published the artcile< New growth-regulating compounds. I. Summary of growth-inhibitory activities of some organic compounds as determined by three tests>, Product Details of C7H4BrNO4, the main research area is .
Growth-regulating substances were prepared and subjected to 3 tests. In each a common reference material, (2,4-dichlorophenoxy)acetic acid (I), was employed and the results of any test were expressed as a percentage of the inhibition produced concurrently by I. The primary test, Test A (Corn Germination Test), involved the determination of inhibition of elongation of the primary root of germinating corn. Corn grains were germinated at 27° in Petri dishes containing 20 mL. of an aqueous solution of the compound to be tested at a concentration of 10 p.p.m. After 4 days of growth the length of the primary root of each plant was measured. Inhibition of growth was determined by subtracting the average length of the primary roots of the treated seeds from that of the control seeds, expressed in percentage. In Test B (Kidney-Bean Single-Droplet Water Test) kidney beans were placed in pots containing 1 lb. soil. After 7-10 days each plant was treated with 0.02 mL. of an aqueous solution containing 200 p.p.m. (4 γ) of the compound to be tested and 0.5% of Carbowax 1500. Treatment was applied to the upper surface of one of the primary leaves at a point along the midrib approx. one-eighth in. from the point of attachment of the blade and petiole. On the 10th day after treatment the fresh weight of that portion of each plant above the second node was determined Controls untreated and also treated with I were included in each test. Test C (Kidney-Bean Single-Droplet Oil Test) was essentially the same as Test B but 0.01 mL. of solution was applied containing 5γ in oil of the compound to be tested. Tri-Bu phosphate, at a concentration of 0.2%, was used as a co-solvent for compounds not directly soluble or miscible with oil. The introduction of I could be accomplished only in this way. Close numerical agreement was not necessarily expected between the 3 tests. The degree of inhibition produced by I in Tests B and C at different times of the year was not wholly identical and was affected by rate of growth. Test A was the most reproducible and formed the primary basis for detection of inhibitory activity and was reliable in separating those compounds that possess a high inhibitory activity for most broad-leaved plants from those with little or no activity at the same concentration Satisfactory agreement was found between Tests A and B with discrepancies in the direction of a lower activity by Test B. Variation between replications was greatest in Test C but the results were satisfactory in separating active inhibitors from those with low activity. Compounds showing high activity are promising for use as herbicides. The compounds tested have been classified into groups according to activity and the results under 3 tests reported. The following, as Group I, are compounds possessing 80% or more of the activity of I in Test A: (2-bromo-4-chlorophenoxy)acetic acid; Bu (2,4,5-trichlorophenoxy) acetate; (2-chloro-4-bromophenoxy)acetic acid; NH4 4-chlorocinnamate; α(4-chlorophenoxy)acetamide; (3-chlorophenoxy)acetic acid; 4-isomer; α-(2,4-dichlorophenoxy)acetamide; 2-(2,4-dichlorophenoxyacetamido)-1-butanol; Na 4-(2,4-dichlorophenoxyacetamido)-2,5-dichlorobenzenesulfonate; 2-(2,4-dichlorophenoxyacetamido)-2-ethyl-1,3-propanediol; 2-(2,4-dichlorophenoxyacetamido)-2-(hydroxymethyl)-1,3-propanediol; 2-(2,4-dichlorophenoxyacetamido)-2-methyl-1,3-propanediol; 2-(2,4-dichlorophenoxyacetamido)-1-naphthalenesulfonic acid; 8-(2,4-dichlorophenoxyacetamido)-1-naphthalenesulfonic acid; 8-(2,4-dichlorophenoxyacetamido)-1-naphthol-3,6-disulfonic acid; (3,4-dichlorophenoxy)acetic acid; 2,5-isomer; (2,4-dichlorophenoxy)acetic anhydride; α-(2,4-dichlorophenoxy)-4-sulfoacetanilide; (2,4-dichlorophenoxy)acetohydroxamic acid; (2,4-dichlorophenoxy) acetyl chloride; (2,4-dichlorophenoxyacetyl)guanidine; N-(2,4-dichlorophenoxyacetyl)urea; α-(2,4-dichlorophenoxy)butyric acid; 2-diethylaminoethyl (2,4-dichlorophenoxy)acetate; 2-diethylaminoethyl (2,4,5-trichlorophenoxy)acetate; 2,2-dimethyl-1,3-dioxolan-4-ylmethyl (2-methyl-4-chlorophenoxy)acetate; 1,4-bis(2,4,5-trichlorophenoxyacetamido)benzene; 1,3-isomer; Et (2,4-dichlorophenoxy)-acetate; Et (2-methyl-4-chlorophenoxy) acetate; Et 2-(2-methyl-4-chlorophenoxy) heptanoate; 2-hydroxyethyl (2,4-dichlorophenoxy)acetate; (2-iodo-4-chlorophenoxy)acetic acid; (2-methyl-4-bromophenoxy)acetic acid; (2-methyl-4-chlorophenoxy)acetamide; N-methyl-α-(4-chlorophenoxy)acetamide; 4-(2-methyl-4-chlorophenoxyacetamido)benzenesulfonic acid; 2-(2-methyl-4-chlorophenoxyacetamido)-6,8-naphthalenedisulfonic acid; 2-(2-methyl-4-chlorophenoxyacetamido)-1-naphthalenesulfonic acid; 8-(2-methyl-4-chlorophenoxyacetamido)-1-naphthalenesulfonic acid; 7-(2-methyl-4-chlorophenoxyacetamido)-1-naphthol-3,6-disulfonic acid; (2-methyl-4-chlorophenoxy)acetic acid; (2-methyl-6-chlorophenoxy)acetic acid; (2-methyl4-chlorophenoxy)acetic anhydride; (2-methyl-4-chlorophenoxy)acetyl chloride; (2-methyl-4-fluorophenoxy)acetic acid; N-methyl-α-(2,4,5-trichlorophenoxy)acetamide; 2-nitro-2-methylpropyl (2,4-dichlorophenoxy)acetate; 2-nitro-2-methylpropyl (2-methyl-4-chlorophenoxy)acetate; Ph chloroacetate; Ph (2-methyl-4-chlorophenoxy)acetate; iso-Pr (2-methyl-4-chlorophenoxy)acetate; 2-(2,4,5-trichlorophenoxyacetamido)-2-(hydroxymethyl)-1,3-propanediol; α-(2,4,5-trichlorophenoxy)-N,N-bis(2-hydroxyethyl)acetamide; (2,4,5-trichlorophenoxy)acetic piperidide; α-(2,4,5-trichlorophenoxy)-3-chloroacetanilide; α-(2,4,5-trichlorophenoxy)-2,4-dimethylacetanilide; α-(2,4,5-trichlorophenoxy)-4-ethoxyacetanilide; α-(2,4,5-trichlorophenoxy)-4-methylacetanilide; α-(2,4,5-trichlorophenoxy)-2,4,6-trichloroacetanilide; [3-(trifluoromethyl)phenoxy] acetic acid; N-[tris(hydroxymethyl)methyl]-N-{2-hydroxy-3-[tris(hydroxymethyl)methylamino]-propyl}-α-(2,4-dichlorophenoxy)acetamide-HCl. The following, as Group II, are compounds possessing 50-79% of the activity of I in Test A: 2-aminoethanol bis-[(4-chlorophenoxy)acetate];(4-bromophenoxy)acetic acid; O-(2-carboxymethoxy-3-methyl-5-bromobenzoyl)glycolic acid; O-(2-carboxymethoxy-3-methyl-5-nitrobenzoyl)-glycolic acid; decyl dihydrogen orthophosphate; (2-chloro-4-tert-butylphenoxy)acetic acid; (2-chloro-4-iodophenoxy)acetic acid; 1-chloronaphthylacetic acid (mixture), ammonium salt; 2-(4-chlorophenoxyacetamido)-1-naphthalenesulfonic acid; 4-(4-chlorophenoxyacetamido)-1-naphthalenesulfonic acid; 8-(4-chlorophenoxyacetamido)-1-naphthalenesulfonic acid; 8-(4-chlorophenoxyacetamido)-1-naphthol-3,6-disulfonic acid; α-(4-chlorophenoxy)-N,N-bis(2-hydroxyethyl)acetamide; (4-chlorophenoxy)acetyl chloride; 2-(4-chlorophenoxyacetamido)-2-(hydroxymethyl)-1,3-propanediol; γ-(4-chlorophenoxy)-butyric acid; S-(4-chlorophenyl)thioglycolic acid; 2-butenyl (4-chlorophenoxy)acetate; (2,4-dibromophenoxy)acetic acid; α,β-dibromo-γ-phenylpropionyl chloride; 3,5-dichloro-2-bromobenzoic acid; (2,4-dichloro-5-bromophenoxy)acetic acid; (2,4-dichlorophenoxy)acetic piperidide; 4-(2,4-dichlorophenoxyacetamido)-1-naphthalenesulfonic acid; (2,4-dichlorophenoxy)acetonitrile; N’-(2,4-dichlorophenoxyacetyl)betaine hydrazide hydrochloride; α-(2,4-dichlorophenoxy)-N,N-diethylacetamide; α-(2,4-dichlorophenoxy-N-methylacetamide; NH4 γ-(2,4-dichlorophenoxy)butyrate; 2,4-dichlorophenylglycine; S-(2,5-dichlorophenyl)thioglycolyl chloride; 2,2-dimethyl-1,3-dioxolan-4-ylmethyl (4-chlorophenoxy)-acetate; β-(2,4-dimethylphenoxy)propionic acid; 3,5-dimethylpyrazole; Et 3-hydroxy-2-naphthoate; Et (2-methyl-4,6-dichlorophenoxy) acetate; 2-hydroxy-3-methyl-5-bromobenzoic acid; 2-hydroxy-3-methyl-5-iodobenzoic acid; 2-hydroxyethyl (4-chlorophenoxy)-acetate; N-2-hydroxyethyl-α-(2,4-dichlorophenoxy)acetamide; N-2-hydroxyethyl-α-(2-methyl-4-chlorophenoxy)-acetamide; 2-hydroxyethyl (2-methyl-4-chlorophenoxy)-acetate; 2-hydroxy-3-methylbenzoic acid; 2-hydroxy-5-nitrobenzoic acid; (2-methyl-4-bromo-6-carboxyphenoxy)acetic acid; α-(3-methyl-4-chlorophenoxy)acetamide; Me (4-chlorophenoxy)acetate; (2-methyl-5-chlorophenoxy)acetic acid; (3-methyl-4-chlorophenoxy)-acetic acid; α-(2-methyl-4-chlorophenoxy)-N,N-bis(2-hydroxyethyl)acetamide; (3-methyl-4-chlorophenoxy)-acetyl chloride; Me (2,4-dibromophenoxy)acetate; Me (2,4-dimethylphenoxy) acetate; (2-methylphenoxy)acetyl chloride; Ph (4-chlorophenoxy)acetate; Ph (2,4-dichlorophenoxy)acetate; α-(2-propyl-4-chlorophenoxy)acetamide; α-(2,4,5-trichlorophenoxy) acetanilide; (2,4,5-trichlorophenoxy)acetonitrile; N-(2,4,5-trichlorophenoxyacetyl) bis[tris(hydroxymethyl) methylaminomethyl] carbinol hydrochloride. The following, as Group III, are compounds possessing 30-49% of the activity of I in Test A: 4-aminoazobenzene; 2-(amylamino)ethyl diphenylacetate-HCl; (2-amyl-4-chlorophenoxy)acetic acid; isoamyl (2,4-dimethylphenoxy)acetate; 2-bromoethyl (4-chlorophenoxy)acetate; (2-bromophenyl)sulfamic acid; butylamine mercuric chloride; Bu (3-methylphenoxy)acetate; cacotheline; 1-(4-carboxyphenyl-3-(3-chlorophenyl)urea; chloroacetamide; 4-chlorobenzoyl chloride; (4-chlorophenoxy)acetonitrile; 1-(4-chlorophenoxy)-2,3-epoxypropane; (4-chlorophenyl)acetic acid; N-(4-chlorophenyl)glycine; S-(4-chlorophenyl)thioglycolyl chloride; N-butyl-S-(4-chlorophenyl)thioglycolamide; [2-(cyanomethyl)-4-chlorophenoxy] acetic acid; NH4 N,N-(cyclopentamethylene)dithiocarbamate; 3,5-dibromo-2-aminobenzoic acid; 2,5-dichloroaniline mercuric chloride salt; (2,4-dichloro-5-aminophenoxy)-acetic acid; 2,4-dichlorocinnamic acid; α-(2,4-dichloro-6-methylphenoxy) acetamide; (2,4-dichloro-5-nitrophenoxy)acetic acid; (2,4-dichlorophenoxy)-N,N-bis(2-hydroxyethyl)acetamide; S-(2,5-dichlorophenyl)thioglycolic acid; 1,1-bis(1-hydroxy-2,2,2-trichloroethyl)urea; 3,4-dimethylphenol; (2,4-dimethylphenoxy)acetic acid; 3,4-isomer; (2,4-dimethylphenoxy)acetyl chloride; S-(2,4-dinitrophenyl)thioglycolic acid; N,N-bis [tris(hydroxymethyl)methyl]ethylenediamine-di-HCl; Et [2-(chloromethyl)-4-chlorophenoxy]acetate; (2-ethyl-4-chlorophenoxy)acetic acid; Et S-(4-chlorophenyl)thioglycolate; 2-hydroxy-3-carboxy-5-chlorotoluene; 4-hydroxy-3,5-dibromobenzoic acid; 2-hydroxyethyl 2,4-dichlorophenyl ether; N4-(iodoacetyl)sulfanilamide; 2-methyl-2-butylaminopropyl 4-(hexyloxy)benzoate-HCl; (2-methyl-4-chloro-6-carboxyphenoxy)acetic acid; Me(2-chlorophenoxy)acetate; 1-(2-methyl-4-chlorophenoxy)-2,3-epoxypropane; Me (2,4-dichlorophenoxy)acetate; (2-methylphenoxy)acetic acid; 4-nitrobenzoyl chloride; octyl dihydrogen orthophosphate; 2-isopropylaminoethyl 2-butoxybenzoate-HCl; Pr (2-methyl-4-chlorophenoxy)acetate; iso-Pr phenylcarbamate; Ba 3-pyridinesulfonate; sulfamerazine; 2,3,5-tribromobenzoic acid; 2,3,5-trichlorobenzoic acid; (2,2,2-trichloro-1-hydroxyethyl)urea; (2,4,6-trichlorophenoxy)acetic acid; (2,4,5-trichlorophenoxy)-2-nitroacetanilide; 2,4,6-trichlorophenyl phenylcarbamate; S-(2,4,5-trichlorophenyl)thioglycolamide; 1-[3-(trifluoromethyl)phenoxy]-2,3-epoxypropane; NH4 2,3,5-triiodobenzoate; N-[tris(hydroxymethyl)methyl]-N-{2-hydroxy-3-[tris(hydroxymethyl)methylamino]propyl}-α-(4-chlorophenoxy)acetamide-HCl. The following, as Group IV-A, are compounds showing less than 29% of the activity of I in Test A and 50% or more of the activity of I in either Test B or Test C: α-amino-β-(2,4-dichlorophenoxy)propionamide; α-amino-β-(3-nitro-4-hydroxyphenyl)propionic acid nitrate salt; aminotetrazole; aniline; (benzylsulfonyl)acetic acid; 5-bromo-2-nitrobenzoic acid; 2-bromo-3-nitrobenzoic acid; NH4 2-bromo-3-nitrobenzoate; β-bromopropionic acid; 2-butylaminoethyl 4-butoxybenzoate-HCl; 2-isobutylaminoethyl 4-butoxybenzoate-HCl; 2-butylaminoethyl 4-ethoxybenzoate-HCl; 2-butylaminoethyl 4-methoxybenzoate-HCl; camphor oxime; N4-(carbo-2-chloroethoxy)sulfanilamide; (2-carbomethoxy-4-chlorophenoxy)acetic acid; (2-carboxy-4-chlorophenoxy)acetic acid; (2-carboxy-6-methylphenoxy)acetic acid; (2-carboxyphenoxy)acetic acid; [2-(carboxymethoxy)-3,5-dichlorobenzoyl]glycolic acid; chloroacetic acid; 2-chloroaniline; 3-chloroaniline; 4-chloroaniline; 4-chlorobenzyl mercaptan; 4-chlorobenzenesulfonyl chloride; 4-chlorobenzylisothiourea-HCl; 4-chloromandelic acid; (2-chloro-4-methylphenoxy)acetic acid; 2-chloro-3-nitrobenzoic acid; 2-chloro-5-nitrobenzoic acid; (2-chlorophenoxy)acetic acid; [2-(2-chlorophenyl)phenoxy]acetic acid; 4-chlorothiophenol; diazoaminobenzene; 2,4-dibromophenol; dichloroacetic acid; 2,4-dichloroaniline; 2,5-dichloroaniline; (2,4-dichlorobenzylsulfonyl)acetic acid; 2,4-dichlorobenzoic acid; 2,4-dichlorobenzylisothiourea-HCl; (2,4-dichloro-6-carboxyphenoxy)acetic acid; (2,6-dichloro-4-nitrophenoxy)acetic acid; 2,4-dichlorophenyl phenylcarbamate; (2,5-dichlorophenyl)sulfamic acid; 2,4-dihydroxypyrimidine; 2,4-dimethylphenol; (2,4-dinitrophenyl)acetic acid; N,N’-bis[tris(hydroxymethyl)methyl] hexamethylenediamine-di-HCl; 3-ethoxy-2-naphthoic acid; 2-ethylaminobutyl 4-ethoxybenzoate-HCl; Et carbamate; Et β-methyl-β-(4-chlorophenyl)glycidate; 3-ethyl-4-methylpyridine; Et (2-propyl-4-chlorophenoxy)acetate; (2-fluorophenoxy)acetic acid; 2-hydroxy-3-bromo-5-chlorobenzoic acid; 2-hydroxy-3-methyl-5-nitrobenzoic acid; N-(2-hydroxy-3-chloropropyl)-p-toluidine; 2-hydroxy-3,5-dinitrobenzoic acid; 4-iodobenzoic acid; 2-methoxyphenol; 4-methoxyphenol; 2-methyl-2-amylaminopropyl diphenylacetate-HCl; 2-methyl-5-chlorophenol; 2-methyl-6-chlorophenol; (2-methyl-4-chlorophenoxy)fumaric acid; Me 3-chlorophenylcarbamate; 2-methyl-4,6-dichlorophenol; 2-methyl-2-hexylaminopropyl 4-ethoxybenzoate-HCl; Me (2-methyl-6-chlorophenoxy)acetate; (4-methylphenoxy)acetic acid; Me phenylthiocarbamate; S-(2-methylphenyl)thioglycolic acid; 4-methyl-4-(trichloromethyl)-2,5-cyclohexadien-1-one O-carboxymethyloxime; 2-nitrobutyl phenylcarbamate; 1-phenyl-3-methyl-5-pyrazole; phthalic acid; α-pinene; 2-isopropylaminoethyl 4-butoxybenzoate-HCl; (2-propyl-4-chlorophenoxy)acetic acid; iso-Pr (2,4-dimethylphenoxy)acetate; iso-Pr (2-methyl-6-chlorophenoxy)acetate; 3-propyl-2-naphthoic acid; iso-Pr (2-propyl-4-chlorophenoxyacetate); trichloroacetamide; trichloroacetic acid; trichloroacetyl chloride; 2,4,5-trichlorobenzenesulfonamide; 3,4,5-trihydroxybenzoic acid; N-[tris(hydroxymethyl)methyl]-2,3-dibromopropylamine-HBr; salicylic acid. The following, as Group IV-B, are compounds insufficiently soluble in water for Test A to be performed but exhibiting 50% or more of the activity of I in either Test B or Test C: allyl (4-chlorophenoxy)acetate; allyl (2,4-dichlorophenoxy)acetate; 2-aminonaphthoic acid; amyl (2,4-dichlorophenoxy)acetate; isoamyl (2,4-dichlorophenoxy)acetate; amyl 1-naphthalenecarbamate; bis-(4-chlorophenyl)(trichloromethyl)methane; 1,1′-(bis-2-naphthol)phenylmethane; 2-bromo-3,5-dichlorobenzamide; 2-bromo-3,5-dichlorobenzanilide; 2,2′-dibromo-3,5-dichlorobenzanilide; 2,3′-dibromo-3,5-dichlorobenzanilide; 2,4′-dibromo-3,5-dichlorobenzanilide; 2-bromo-3,3′,5-trichlorobenzanilide; 2-bromo-2′,3,4′,5-tetrachlorobenzanilide; 2-bromo-3,5-dichloro-m-benzotoluidide; 2-bromo-3,5-dichlorobenzoyl chloride; 2-bromoethyl (2,4-dibromophenoxy) acetate; 2-bromoethyl (2,4-dichlorophenoxy) acetate; α-(4-bromophenoxy)acetamide; 1-(3-bromophenyl)-3-(2-chlorophenyl)urea; 1-(3-bromophenyl)-3-(3-chlorophenyl)urea; Bu (2,4-dichlorophenoxy)acetate; iso-Bu (2,4-dichlorophenoxy)acetate; 1-carbethoxy-3-(3-chlorophenyl)urea; 2-chloroethyl (4-chlorophenoxy)acetate; 2-chloroethyl (2,4-dibromophenoxy)acetate; 2-chloroethyl (2,4-dichlorophenoxy)acetate; 2-chloroethyl (2-methyl-4-chlorophenoxy)acetate; 2-chloroethyl 1-naphthalenecarbamate; 2-chloroethyl phenylcarbamate; α-(4-chlorophenoxy)-p-acetanisidide; α-(4-chlorophenoxy)-2-bromoacetanilide; α-(4-chlorophenoxy)-3-bromoacetanilide; α-(4-chlorophenoxy)-4-bromoacetanilide; α-(4-chlorophenoxy)-2-chloroacetanilide; α-(4-chlorophenoxy)-3-chloroacetanilide; α-(4-chlorophenoxy)-2,4-dimethylacetanilide; α-(4-chlorophenoxy)-4-ethoxyacetanilide; 1-(4-chlorophenoxyacetyl)-2-phenylhydrazine; α-(4-chlorophenoxy)-4-iodoacetanilide; α-(4-chlorophenoxy)-3-nitroacetanilide; α-(4-chlorophenoxy)-p-acetotoluidide; α-(4-chlorophenoxy)-N-p-xenylacetamide; γ-(4-chlorophenoxy)butyronitrile; 4-chlorophenyl (4-chlorophenoxy)acetate; 1-(4-chlorophenyl)-3-(2-chlorophenyl) urea; 4-chlorophenyl (2,4-dichlorophenoxy)acetate; 1-(3-chlorophenyl)-3,3-(cyclopentamethylene)urea; 1-(3-chlorophenyl-3-phenylurea; S-(4-chlorophenyl)-2-bromothioglycolanilide; S-(4-chlorophenyl)-3-bromothioglycolanilide; 4-chlorophenyl (2,4,5-trichlorophenoxy)acetate; 2,6-dibromobenzoquinone-4-chloroimide; 2,4-dichlorobenzylsulfonyl chloride; 1,3-bis(4-chlorophenoxyacetamido)benzene; 1,4-isomer; 4,4′-bis(4-chlorophenoxyacetamido)biphenyl; 2,4-bis(4-chlorophenoxyacetamido)toluene; α-(2,4-dichlorophenoxy)acetanilide; α-(2,4-dichlorophenoxy)-N-(2-aminoethyl)acetamide; α-(2,4-dichlorophenoxy)-p-acetanisidide; α-(2,4-dichlorophenoxy-2,5-dichloroacetanilide; α-(2,4-dichlorophenoxy)-2,4-dimethylacetanilide; 1-(2,4-dichlorophenoxyacetyl)-2-(2,4-dinitrophenyl)hydrazine; (2,4-dichlorophenoxy)acetic hydrazide; α-(2,4-dichlorophenoxy)aceto-2-naphthalide; α-(2,4-dichlorophenoxy)-p-acetotoluidide; α-(2,4-dichlorophenoxy)-N-o-xenylacetamide; 4-(2,4-dichlorophenoxyacetamido)azobenzene; (2,4-dichlorophenoxy)acetylaminoguanidine; (2,4-dichlorophenoxy)acetyl bromide; α-(2,4-dichlorophenoxy)-N-(hydroxy-tert-butyl)acetamide; S-(2,4-dichlorophenoxyacetyl)isothiourea; 1-(2,4-dichlorophenoxyacetyl)-2-methyl-2-thioisourea; γ-(2,4-dichlorophenoxy)butyric acid; γ,-(2,4-dichlorophenoxy)butyronitrile; 2,4-dichlorophenyl (4-chlorophenoxy)acetate; 2,4-dichlorophenyl (2,4-dichlorophenoxy)acetate; 1-(2,5-dichlorophenyl)-3-phenylurea; S-(2,5-dichlorophenyl)thioglycolamide; 4,4′-bis(2,4-dichlorophenoxyacetamido)biphenyl; 1,4-bis (2,4-dimethylphenoxyacetamido)benzene; 2,4-bis(2,4-dimethylphenoxyacetamido)toluene; 2,4-dichlorophenyl (2,4,5-trichlorophenoxy)acetate; 2,4-dichlorophenyl (4-chlorophenoxy)acetate; 2,3-dichloropropyl (2,4-dibromophenoxy)acetate; 2,3-dichloropropyl (2,4-dichlorophenoxy)acetate; 2-diethylaminoethyl 2,3,5-triiodobenzoate; 3,3′-dimethyl-4,4′-bis(4-chlorophenoxyacetamido)biphenyl; 3,3′-dimethyl-4,4′-bis(2-methylphenoxyacetamido)biphenyl; 1,3-bis(2-methylphenoxyacetamido)benzene; 1,4-isomer; 4,4′-bis(2-methylphenoxyacetamido)biphenyl; 4,4′-bis(2,4-dimethylphenoxyacetamido)biphenyl; 1-(4-ethoxyphenyl)-3-phenylurea; Et 2-bromo-3,5-dichlorobenzoate; Et (4-bromophenoxy)acetate; Et (4-chlorophenoxy)acetate; 2-ethylhexyl (2,4-dichlorophenoxy)acetate; methallyl (4-chlorophenoxy)acetate; 2-methoxy-4-methylphenyl 1-naphthalenecarbamate; Me 2-bromo-3-nitrobenzoate; 4-(2-methyl-4-chlorophenoxyacetamido)azobenzene; α-(2-methyl-6-chlorophenoxy)-2,5-dichloroacetanilide; 2-methyl-4-chlorophenyl (2,4-dichlorophenoxy)acetate; 1-methyl-2,4-bis(2,4-dichlorophenoxyacetamido)benzene; Me 4-nitrophenylcarbamate; Me (2,4,5-trichlorophenoxy)acetate; (2-hydroxy-1-naphthyl)-1-piperidylphenylmethane; 2-nitrobutyl (2,4,5-trichlorophenoxy)acetate; 4-nitro-N,N-dimethylaniline; octyl (2,4-dichlorophenoxy)acetate; pentachlorophenyl (2,4,5-trichlorophenoxy)acetate; 1-phenyl-3,3-cyclopentamethyleneurea; Ph phenylcarbamate; Ph (2,4,5-trichlorophenoxy)acetate; iso-Pr (2,4-dichlorophenoxy)acetate; 3-isopropoxy-2-naphthoic acid; 1,3-di-m-tolyl-urea; (2,4,5-tribromo-3,5-dimethylphenoxy)acetic acid; 2,4,6-tribromophenyl acetate; 2,4,5-trichlorobenzamide; trichloroethyl (2,4-dibromophenoxy)acetate; 2,2,2-trichloroethyl (2,4-dichlorophenoxy)acetate; 2,4,5-trichlorophenoxyacetic acid; 2-(2,4,5-trichlorophenoxyacetamido)anthraquinone; α-(2,4,5-trichlorophenoxy)-4-bromoacetanilide; α-(2,4,5-trichlorophenoxy)-4-methoxyacetanilide; (2,4,5-trichlorophenoxy)aceto-2-naphthalide; α-(2,4,6-trichlorophenoxy)-4-sulfoacetonaphthalide; α-(2,4,5-trichlorophenoxy)-m-acetotoluidide; (2,4,5-trichlorophenoxy)acetyl chloride; 1-(2,4,5-trichlorophenoxyacetyl)-2-(p-nitrophenyl)hydrazine; 2,4,6-trichlorophenyl (4-chlorophenoxy)acetate; 2,4,6-trichlorophenyl (2,4-dichlorophenoxy)acetate; 2,4,6-trichlorophenyl (2,4,5-trichlorophenoxy)acetate; N-[3-(trifluoromethyl)phenyl]-α-(4-chlorophenoxy)acetamide; N-[3-(trifluoromethyl)phenyl]-α-(2,4,5-trichlorophenoxy)acetamide; 2,3,5-triiodobenzoic acid; 2,3,5-triiodobenzoyl chloride; 1-[tris(hydroxymethyl)methylamino]-2,4-dinitrobenzene; N-(p-xenyl)-α-(2,4-dichlorophenoxy)acetamide. The following, as Group IV-C, were also examined by the three tests and showed relatively low activity as compared with I: 2-acetoxyethyl 1-naphthalenecarbamate; 2-acetoxyethyl phenylcarbamate; (2-acetyl-4-chlorophenoxy)acetic acid; (2-allyl-4-chlorophenoxy)acetic acid; allyl 1-naphthalenecarbamate; allyl phenylcarbamate; allyl 4-tolyl sulfone; 1-aminoanthraquinone; 2-isomer; 4-aminobenzyl tris(hydroxymethyl)methylamine-di-HCl; 2-amino-3,5-dichlorobenzoic acid; 2-aminoethylsulfuric acid; 8-amino-1-naphthol-3,6-disulfonic acid; 1-amino-2-naphthol-4-sulfonic acid; 4-aminophenol; (2-aminophenoxy)acetic acid; (4-aminophenyl)acetic acid; 2-aminopyridine; 2-aminothiazole; 2-amylaminoethyl 4-butoxybenzoate-HCl; isoamyl formate; amyl (2-methylphenoxy)acetate; isoamyl 1-naphthalenecarbamate; 4-tert-amylphenol; amyl phenylcarbamate; isoamyl phenylcarbamate; (4-arsonophenoxy)acetic acid; benzoic acid; 4-benzylaminophenol-HCl; benzyl Bu sulfone; allyl (benzylsulfonyl)acetate; Me (benzylsulfonyl)acetate; N-benzyl-N,N’-bis[tris(hydroxymethyl)methyl]-2-hydroxy-1,3-diaminopropane; benzyl Et sulfone; benzyl Me sulfone; benzyl 4-tolyl sulfone; benzyl[tris(hydroxymethyl)methyl]amine; 1,3-bis{ [tris(hydroxymethyl)methyl]amino}-2-propanol-HCl; 2-bromobenzamide; 2-bromobenzanilide; 2-bromo-2′,4′-dichlorobenzanilide; 2-bromobenzoic acid; 3-isomer; NH4 4-bromobenzoate; 4-bromobenzonitrile; (2-bromo-4-tert-butylphenoxy)acetic acid; 2-bromo-3,5-dichloro-N-butylbenzamide; 2-bromo-3,4′,5-trichlorobenzanilide; 2-bromoethylamine; 2-bromoethyl 4-ethoxythiolbenzoate; 2-bromoethyl (2-methyl-4-chlorophenoxy)acetate; 2-bromo-4-nitrobenzoic acid; 2-bromo-5-nitrobenzoic acid; NH4 2-bromo-5-nitrobenzoate; 3-bromo-4-nitrobenzoic acid; 3-bromo-5-nitrobenzoic acid; 4-bromophenol; (2-bromophenoxy)acetic acid; α-(4-bromophenoxy)-4-bromoacetanilide; α-(4-bromophenoxy)-4-chloroacetanilide; α-(4-bromophenoxy)-2,5-dichloroacetanilide; 3-bromophenylammonium fluoroborate; 4-bromophenylammonium fluoroborate; 1-(2-bromophenyl)-3-(2-chlorophenyl)urea; 1-(4-bromophenyl)-3-(3-chlorophenyl)urea; 1-(2-bromophenyl)-3-(3-chlorophenyl)urea; N-(4-bromophenyl)-3-(2-chlorophenyl)urea; NH4 (4-bromophenyl)dithiocarbamate; 4-bromophenyl 1-naphthalenecarbamate; (2-bromo-4-phenylphenoxy)acetic acid; 4-bromophenyl phenylcarbamate; 1-(2-bromophenyl)-3-phenylurea; 1-(3-bromophenyl)-3-phenylurea; 1-(4-bromophenyl)-3-phenylurea; 3-bromophenylsulfamic acid; N-(3-bromophenyl) α,α,α-trichloroacetamide; 2-butylaminoethyl 2-butoxybenzoate-HCl; 2-butylaminoethyl diphenylacetate-HCl; 2-butylaminoethyl 4-(heptyloxy)benzoate-HCl; 2-butylaminoethyl 4-propoxybenzoate-HCl; 2-butylaminoethyl 2-(thiobutoxy)benzoate; (2-sec-butyl-4-chlorophenoxy)acetic acid; Hg butyldithiocarbamate; Bu 1-naphthalenecarbamate; iso-Bu 1-naphthalenecarbamate; 4-tert-butylphenol; Bu phenylcarbamate; iso-Bu phenylcarbamate; tert-Bu phenylcarbamate; 1-butyl-3-phenylthiourea; N-butyl-α-(2,4,5-trichlorophenoxy)acetamide; 4-carbethoxy-6-methoxyquinoline; 1-carbethoxy-3-phenylurea; 1-carbobutoxyethyl 1-naphthalenecarbamate; 1-carboisopropoxyethyl 1-naphthalenecarbamate; O-(2-carboxymethoxybenzoyl)glycolic acid; O-(2-carboxymethoxy-3-methyl-5-chlorobenzoyl)glycolic acid; NH4 (carboxymethyl)dithiocarbamate; Na (4-carboxymethylphenyl)dithiocarbamate; 2-carboxy-6-methylphenyl phenylcarbamate; NH4 (4-carboxyphenyl)dithiocarbamate; 4-carboxyphenylglycine; o-carboxyphenyl 1-naphthalenecarbamate; 1-(4-carboxyphenyl)-3-(1-naphthyl)urea; 4-carboxyphenyl phenylcarbamate; S-(4-carboxyphenyl)thioglycolic acid; N4-(β-carboxypropionyl)sulfanilamide; pyrocatechol; chloroacetyl chloride; 4-chloroanisole; 2-chlorobenzaldehyde O-carboxymethyloxime; 2-chlorobenzaldehyde oxime; 4-chlorobenzamide; 4-chlorobenzenesulfonamide; 4-chlorobenzoic acid; bis(4-chlorobenzyl)disulfide; S-(4-chlorobenzyl)thioglycolic acid; bis(4-chlorobenzyl)sulfide; (4-chlorobenzylsulfonyl)acetic acid; 4-chlorocinnamic acid; highly chlorinated 1,5-dihydroxynaphthalene; 2-chloroethyl (2-propyl-4-chlorophenoxy)acetate; chlorohydroquinone; chlorohydroquinone-O,O-diacetic acid; 4-(chloromercuri)phenol; [4-(chloromercuri)phenoxy]acetic acid; [2-(chloromethyl)-4-chlorophenoxy]acetic acid; 2-chloro-4-methyl-6-methoxyquinoline; 2-chloro-4-methylquinoline; (7-chloro-1-naphthoxy)acetic acid; 1-chloronaphthylacetic acid mixture; 4-chlorophenetole; 1-(4-chlorophenoxyacetamido)naphthalene; 2-(4-chlorophenoxyacetamido)naphthalene; α-(4-chlorophenoxy)-2,5-dichloroacetanilide; α-(4-chlorophenoxy)-N,N-diethyl-acetamide; (4-chlorophenoxy)acetic piperidide; α-(4-chlorophenoxy)-2-nitroacetanilide; α-(4-chlorophenoxy)-2,4,6-trichloroacetanilide; (4-chlorophenoxy)(4-chlorophenyl)acetic acid; (4-chlorophenoxy)fumaric acid; 2-(4-chlorophenoxy)heptanoic acid; β-(4-chlorophenoxy)propionic acid; β-(4-chlorophenoxy)propionitrile; 4-chlorophenylammonium fluoroborate; 1-(2-chlorophenyl)-3-butylurea; 1-(3-chlorophenyl)-3-butylurea; 1-(2-chlorophenyl)-1-(4-carboxyphenyl)urea; N-(3-chlorophenyl)-α-chloroacetamide; 4-isomer; 1-(3-chlorophenyl)-3-(2-chlorophenyl) urea; 1-(4-chlorophenyl)-3-(3-chlorophenyl) urea; 3-(2-chlorophenyl)-1,1-cyclopentamethyleneurea; NH4 (4-chlorophenyl)dithiocarbamate; 2-chloro-1,4-phenylene bis(phenylcarbamate); N-(2-chlorophenyl)glycine; 1-(2-chlorophenyl)-3-(2-hydroxyethyl) urea; 3-chloro isomer; 3-chlorophenyl isocyanate; 1-(2-chlorophenyl)-3-(1-naphthyl) urea; 4-isomer; [2-(4-chlorophenyl)phenoxy]acetic acid; 1-(2-chlorophenyl)-3-phenylurea; 4-chloro isomer; 1-(2-chlorophenyl)-3-phenylthiourea; 3-isomer; 4-isomer; Na (3-chlorophenyl)sulfamate; (4-chlorophenyl)sulfamic acid; S-(2-chlorophenyl)thioglycolic acid; S-(4-chlorophenyl)thioglycolamide; S-(4-chlorophenyl)thioglycolanilide; S-(4-chlorophenyl)-4′-bromothioglycolanilide; S-(4-chlorophenyl)thioglycol-p-phenetidide; S-(4-chlorophenyl)thioglycol-m-toluidine; 1-(2-chlorophenyl)urea; 3-isomer; 1,3-bis(2-chlorophenyl)urea; 3-isomer; cinnamic acid; cinnamoyl chloride; o-cresol; m-isomer; p-isomer; 4-toloxyacetyl chloride; cyanoacetamide; (2-cyclohexyl-4-chlorophenoxy)acetic acid; (decyl-mercapto)acetic acid; (decylsulfonyl)acetic acid; bis(2-acetoxyethyl) sulfone; 2,6-diaminopyridine monohydrochloride; 2,6-dibromo-4-carboxyphenyl phenylcarbamate; α,β-dibromodihydrocinnamic acid; 4,6-dibromo-1,3-dihydroxybenzene; (2,6-dibromo-4-methylphenoxy)acetic acid; 2,4-dibromophenyl phenylcarbamate; α, β-dibromo-γ-phenylpropionamide; bis(2-butyroxyethyl) sulfone; 2,5-dichloro-4-aminobenzenesulfonic acid; 2,4-dichloroanisole; 2,6-dichlorobenzenoneindophenol sodium salt; 2,5-dichlorobenzenesulfonamide; 2,5-dichlorobenzenesulfonyl chloride; (2,4-dichlorobenzylmercapto)acetic acid; bis(2,4-dichlorobenzyl)disulfide; 2,4-dichlorobenzyl mercaptan; bis(2,4-dichlorobenzyl)sulfide; bis(2,4-dichlorobenzyl)sulfone; 5,7-dichloro-3-coumaranone; N,2,4-trichloroacetanilide; 2,6-dichloro-3-ethyl-4-methylpyridine; 2,4-dichloromandelic acid; 2,6-dichloro-4-methyl-5-ethylnicotinamide; (2,6-dichloro-4-methylphenoxy)acetic acid; (2,4-dichloro-6-methylphenoxy)acetyl chloride; (2,4-dichloro-1-naphthoxy)acetic acid; 2,4-dichlorophenetole; 2,4-dichlorophenol; 1-(2,4-dichlorophenoxyacetamido)anthraquinone; 2-(2,4-dichlorophenoxyacetamido)anthraquinone; (2,6-dichlorophenoxy)acetic acid; 3,5-isomer; α-(2,4-dichlorophenoxy)-4-bromoanilide; α-(2,4-dichlorophenoxy)-4-chloroacetanilide; α-(2,4-dichlorophenoxy)-p-acetophenetide; α-(2,4-dichlorophenoxy)-N-(2-hydroxyethyl)acetamide; 2,4-dichlorophenoxyaceto-1-naphthalide; α-(2,4-dichlorophenoxy)-2-nitroacetanilide; α-(2,4-dichlorophenoxy)-3-nitroacetanilide; 1-(2,4-dichlorophenoxyacetyl)-2-(p-nitrophenyl)hydrazine; α-(2,4-dichlorophenoxy)-N-2′-pyridylacetamide; α-(2,4-dichlorophenoxy)-2,4,6-trichloroacetanilide; 2-(2,4-dichlorophenoxyacetamido)-6,8-naphthalenedisulfonic acid; 1-(2,4-dichlorophenoxyacetyl)-1-phenylsemicarbazide; (2,4-dichlorophenoxy)(p-chlorophenyl)acetic acid; 1-(2,4-dichlorophenoxy)-2,3-epoxypropane; (2,4-dichlorophenoxy) fumaric acid; Addnl. information in printed abstract
Botanical Gazette (Chicago) published new progress about Hormones, plant Role: BIOL (Biological Study). 16426-64-5 belongs to class bromides-buliding-blocks, and the molecular formula is C7H4BrNO4, Product Details of C7H4BrNO4.
Referemce:
Bromide – Wikipedia,
bromide – Wiktionary