US3298818A - Tetrahalobenzoic acid-nu-phenyl-nu', nu'-dialkylurea herbicide compositions - Google Patents
Tetrahalobenzoic acid-nu-phenyl-nu', nu'-dialkylurea herbicide compositions Download PDFInfo
- Publication number
- US3298818A US3298818A US109851A US10985161A US3298818A US 3298818 A US3298818 A US 3298818A US 109851 A US109851 A US 109851A US 10985161 A US10985161 A US 10985161A US 3298818 A US3298818 A US 3298818A
- Authority
- US
- United States
- Prior art keywords
- acid
- phenyl
- urea
- dimethylurea
- ammonium
- 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 - Lifetime
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- 239000000203 mixture Substances 0.000 title claims description 30
- 230000002363 herbicidal effect Effects 0.000 title claims description 19
- 239000004009 herbicide Substances 0.000 title description 8
- UYGUFXUBSNDUFA-UHFFFAOYSA-N 2,3,5,6-tetrachlorobenzoic acid Chemical compound OC(=O)C1=C(Cl)C(Cl)=CC(Cl)=C1Cl UYGUFXUBSNDUFA-UHFFFAOYSA-N 0.000 claims description 15
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical class NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 14
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 9
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims description 5
- 150000003863 ammonium salts Chemical class 0.000 claims description 5
- 150000001875 compounds Chemical class 0.000 claims description 5
- YJDNWACSPIXKRT-UHFFFAOYSA-N 2,3,5,6-tetrachlorobenzamide Chemical compound ClC1=C(C(=O)N)C(=C(C=C1Cl)Cl)Cl YJDNWACSPIXKRT-UHFFFAOYSA-N 0.000 claims description 2
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical group [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims 1
- 241000196324 Embryophyta Species 0.000 description 20
- 235000013877 carbamide Nutrition 0.000 description 18
- 239000004202 carbamide Substances 0.000 description 16
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 12
- 229910052708 sodium Inorganic materials 0.000 description 12
- 239000011734 sodium Substances 0.000 description 12
- 239000002253 acid Substances 0.000 description 11
- 150000003839 salts Chemical class 0.000 description 8
- 125000000217 alkyl group Chemical group 0.000 description 7
- 238000009472 formulation Methods 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 239000002671 adjuvant Substances 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 230000002195 synergetic effect Effects 0.000 description 5
- -1 N-(p-chlorophenyl)-N,N'-diisopropylurea Chemical compound 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 239000002689 soil Substances 0.000 description 4
- XZTUYISAOWDOSC-UHFFFAOYSA-N 1-(4-chlorophenyl)-1,3-dimethylurea Chemical compound CNC(=O)N(C)C1=CC=C(Cl)C=C1 XZTUYISAOWDOSC-UHFFFAOYSA-N 0.000 description 3
- 244000298479 Cichorium intybus Species 0.000 description 3
- 235000007542 Cichorium intybus Nutrition 0.000 description 3
- 235000003805 Musa ABB Group Nutrition 0.000 description 3
- 235000015266 Plantago major Nutrition 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000012669 liquid formulation Substances 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 239000000080 wetting agent Substances 0.000 description 3
- XMTQQYYKAHVGBJ-UHFFFAOYSA-N 3-(3,4-DICHLOROPHENYL)-1,1-DIMETHYLUREA Chemical compound CN(C)C(=O)NC1=CC=C(Cl)C(Cl)=C1 XMTQQYYKAHVGBJ-UHFFFAOYSA-N 0.000 description 2
- 241000217446 Calystegia sepium Species 0.000 description 2
- 241000508725 Elymus repens Species 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 240000008790 Musa x paradisiaca Species 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- IXWIAFSBWGYQOE-UHFFFAOYSA-M aluminum;magnesium;oxygen(2-);silicon(4+);hydroxide;tetrahydrate Chemical compound O.O.O.O.[OH-].[O-2].[O-2].[O-2].[O-2].[O-2].[O-2].[O-2].[O-2].[O-2].[O-2].[Mg+2].[Al+3].[Si+4].[Si+4].[Si+4].[Si+4] IXWIAFSBWGYQOE-UHFFFAOYSA-M 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 150000008064 anhydrides Chemical class 0.000 description 2
- 150000001768 cations Chemical class 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- 239000003995 emulsifying agent Substances 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- IZUPBVBPLAPZRR-UHFFFAOYSA-N pentachlorophenol Chemical compound OC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl IZUPBVBPLAPZRR-UHFFFAOYSA-N 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 230000000885 phytotoxic effect Effects 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- LZMATGARSSLFMQ-UHFFFAOYSA-N propan-2-ylurea Chemical compound CC(C)NC(N)=O LZMATGARSSLFMQ-UHFFFAOYSA-N 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 230000001954 sterilising effect Effects 0.000 description 2
- 238000004659 sterilization and disinfection Methods 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- 150000003672 ureas Chemical class 0.000 description 2
- XBUCDZCDAXWTPJ-UHFFFAOYSA-N 1,1-dibenzyl-3-(4-chlorophenyl)urea Chemical compound C1=CC(Cl)=CC=C1NC(=O)N(CC=1C=CC=CC=1)CC1=CC=CC=C1 XBUCDZCDAXWTPJ-UHFFFAOYSA-N 0.000 description 1
- ZWOULFZCQXICLZ-UHFFFAOYSA-N 1,3-dimethyl-1-phenylurea Chemical compound CNC(=O)N(C)C1=CC=CC=C1 ZWOULFZCQXICLZ-UHFFFAOYSA-N 0.000 description 1
- PMOGVVMUSYQXOP-UHFFFAOYSA-N 1-(2-hydroxyethyl)-1-phenylurea Chemical compound OCCN(C(=O)N)C1=CC=CC=C1 PMOGVVMUSYQXOP-UHFFFAOYSA-N 0.000 description 1
- XJHOEDPXONTXQU-UHFFFAOYSA-N 1-benzyl-1-phenylurea Chemical compound C=1C=CC=CC=1N(C(=O)N)CC1=CC=CC=C1 XJHOEDPXONTXQU-UHFFFAOYSA-N 0.000 description 1
- 239000005631 2,4-Dichlorophenoxyacetic acid Substances 0.000 description 1
- RPWNGWJCRXDKJU-UHFFFAOYSA-N 2-(2,3,4,5-tetrachlorophenyl)acetic acid Chemical class OC(=O)CC1=CC(Cl)=C(Cl)C(Cl)=C1Cl RPWNGWJCRXDKJU-UHFFFAOYSA-N 0.000 description 1
- PAWQVTBBRAZDMG-UHFFFAOYSA-N 2-(3-bromo-2-fluorophenyl)acetic acid Chemical compound OC(=O)CC1=CC=CC(Br)=C1F PAWQVTBBRAZDMG-UHFFFAOYSA-N 0.000 description 1
- BZSXEZOLBIJVQK-UHFFFAOYSA-N 2-methylsulfonylbenzoic acid Chemical compound CS(=O)(=O)C1=CC=CC=C1C(O)=O BZSXEZOLBIJVQK-UHFFFAOYSA-N 0.000 description 1
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 description 1
- PWLKEIDJQXTQCX-UHFFFAOYSA-N 3-phenyl-1,1-di(propan-2-yl)urea Chemical compound CC(C)N(C(C)C)C(=O)NC1=CC=CC=C1 PWLKEIDJQXTQCX-UHFFFAOYSA-N 0.000 description 1
- 240000001592 Amaranthus caudatus Species 0.000 description 1
- 235000009328 Amaranthus caudatus Nutrition 0.000 description 1
- 244000036975 Ambrosia artemisiifolia Species 0.000 description 1
- 235000003129 Ambrosia artemisiifolia var elatior Nutrition 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 244000089742 Citrus aurantifolia Species 0.000 description 1
- 235000008733 Citrus aurantifolia Nutrition 0.000 description 1
- 241000207894 Convolvulus arvensis Species 0.000 description 1
- 244000000626 Daucus carota Species 0.000 description 1
- 235000002206 Daucus carota subsp carota Nutrition 0.000 description 1
- 241000123589 Dipsacus Species 0.000 description 1
- 206010061217 Infestation Diseases 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 241000234295 Musa Species 0.000 description 1
- XGEGHDBEHXKFPX-UHFFFAOYSA-N N-methylthiourea Natural products CNC(N)=O XGEGHDBEHXKFPX-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 240000007019 Oxalis corniculata Species 0.000 description 1
- 235000016499 Oxalis corniculata Nutrition 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 244000197975 Solidago virgaurea Species 0.000 description 1
- 235000000914 Solidago virgaurea Nutrition 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- SAQSTQBVENFSKT-UHFFFAOYSA-M TCA-sodium Chemical compound [Na+].[O-]C(=O)C(Cl)(Cl)Cl SAQSTQBVENFSKT-UHFFFAOYSA-M 0.000 description 1
- 235000011941 Tilia x europaea Nutrition 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 150000008055 alkyl aryl sulfonates Chemical class 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 235000003484 annual ragweed Nutrition 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 159000000032 aromatic acids Chemical class 0.000 description 1
- 229910052788 barium Inorganic materials 0.000 description 1
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
- 235000005770 birds nest Nutrition 0.000 description 1
- 235000006263 bur ragweed Nutrition 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 150000001767 cationic compounds Chemical class 0.000 description 1
- BIWJNBZANLAXMG-YQELWRJZSA-N chloordaan Chemical compound ClC1=C(Cl)[C@@]2(Cl)C3CC(Cl)C(Cl)C3[C@]1(Cl)C2(Cl)Cl BIWJNBZANLAXMG-YQELWRJZSA-N 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 235000003488 common ragweed Nutrition 0.000 description 1
- 230000003750 conditioning effect Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- MZGNSEAPZQGJRB-UHFFFAOYSA-N dimethyldithiocarbamic acid Chemical class CN(C)C(S)=S MZGNSEAPZQGJRB-UHFFFAOYSA-N 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000012990 dithiocarbamate Substances 0.000 description 1
- 150000004659 dithiocarbamates Chemical class 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 230000008029 eradication Effects 0.000 description 1
- 239000003337 fertilizer Substances 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- VUNCWTMEJYMOOR-UHFFFAOYSA-N hexachlorocyclopentadiene Chemical compound ClC1=C(Cl)C(Cl)(Cl)C(Cl)=C1Cl VUNCWTMEJYMOOR-UHFFFAOYSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 150000003949 imides Chemical class 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000004571 lime Substances 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- XGEGHDBEHXKFPX-NJFSPNSNSA-N methylurea Chemical compound [14CH3]NC(N)=O XGEGHDBEHXKFPX-NJFSPNSNSA-N 0.000 description 1
- 239000010445 mica Substances 0.000 description 1
- 229910052618 mica group Inorganic materials 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- BMLIZLVNXIYGCK-UHFFFAOYSA-N monuron Chemical compound CN(C)C(=O)NC1=CC=C(Cl)C=C1 BMLIZLVNXIYGCK-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 150000002892 organic cations Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 229940051841 polyoxyethylene ether Drugs 0.000 description 1
- 229920000056 polyoxyethylene ether Polymers 0.000 description 1
- 239000013014 purified material Substances 0.000 description 1
- 235000009736 ragweed Nutrition 0.000 description 1
- ODCWYMIRDDJXKW-UHFFFAOYSA-N simazine Chemical compound CCNC1=NC(Cl)=NC(NCC)=N1 ODCWYMIRDDJXKW-UHFFFAOYSA-N 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- GUHWQVZRQNQCRJ-UHFFFAOYSA-M sodium 2,3,5,6-tetrachlorobenzoate Chemical compound ClC1=C(C(=O)[O-])C(=C(C=C1Cl)Cl)Cl.[Na+] GUHWQVZRQNQCRJ-UHFFFAOYSA-M 0.000 description 1
- 235000010339 sodium tetraborate Nutrition 0.000 description 1
- PDEFQWNXOUGDJR-UHFFFAOYSA-M sodium;2,2-dichloropropanoate Chemical compound [Na+].CC(Cl)(Cl)C([O-])=O PDEFQWNXOUGDJR-UHFFFAOYSA-M 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 229910052712 strontium Inorganic materials 0.000 description 1
- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 description 1
- 230000009044 synergistic interaction Effects 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- VLCLHFYFMCKBRP-UHFFFAOYSA-N tricalcium;diborate Chemical class [Ca+2].[Ca+2].[Ca+2].[O-]B([O-])[O-].[O-]B([O-])[O-] VLCLHFYFMCKBRP-UHFFFAOYSA-N 0.000 description 1
- BSVBQGMMJUBVOD-UHFFFAOYSA-N trisodium borate Chemical class [Na+].[Na+].[Na+].[O-]B([O-])[O-] BSVBQGMMJUBVOD-UHFFFAOYSA-N 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
- 235000005765 wild carrot Nutrition 0.000 description 1
- 230000003245 working effect Effects 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- JLYXXMFPNIAWKQ-UHFFFAOYSA-N γ Benzene hexachloride Chemical compound ClC1C(Cl)C(Cl)C(Cl)C(Cl)C1Cl JLYXXMFPNIAWKQ-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
- A01N47/30—Derivatives containing the group >N—CO—N aryl or >N—CS—N—aryl
Definitions
- This invention relates to novel compositions of matter comprising ureas and certain tetrahalogenated aromatic acids and its derivatives useful as herbicides, which exhibit unobvious and enhanced herbicidal acitivity not logically predictable from the individual properties of the components by themselves.
- this invention describes synergistic herbicidal combinations of N-phenyl-N',N'-dialkylureas and a member of the group selected from 2,3,5.,6-tetrachlorobenzoic acid, the salts of 2,3,5,6-tetrachlorobenzoic acids and the derivatives of 2,3,5,6-tetrachlorobenzoic acid.
- Suitable salts include those which contain an inorganic or organic cation such as sodium, potassium, calcium, strontium, barium, magnesium, aluminum, iron, cobalt, nickel, zinc, ammonium, mono-, di-, trialkyl and 'alkanol amonium salts.
- Suitable derivatives include but are not limited to the esters, amides, imides, acid chloride, and anhydrides of 2,3,5,6-tetrachlorobenzoic acid.
- N- 3 ,4-dichlorophenyl -N',N'-di.methylurea N-(p-chlorop-henyl)-N,N-dimethylurea, N-n-butyl-N- 3 ,4-dichlorophenyl) -N-methylurea, N- phenyl-N-(2-hydroxyethyl)urea,
- N- 3,4-dichlorophenyl) -N-cyclohexy1 urea N-(p-chlorophenyl-N'-cycl0hexyl) urea, N-phenyl-N',N'-diisopropylurea,
- the synergistic herbicidal combinations of this invention offer several advantages over herbicidal compositions of the prior art. For example, the total herbicidal efiect of these combinations of urea and acid have been found to be greater than the individual herbicidal effect of either component taken additively. This enhancement or potentiation is manifested in several ways, all of which are of practical value to the user.
- the rate of application that is needed to control the weed populace is significantly reduced; the phytotoxic effect seems to be accelerated resulting in more rapid kill; there seems to be a longer term regression of the weed populations regrowth, or expressed another way, a longer term sterilization of the soil results; lastly, there appears to be a more pronounced eifect against weeds recalcitrant to the phytot-oxic effect of the individual herbicides.
- This long term sterilization coup-led with low rates of application make the inventive compositions especially suitable for use on low value land such as rights of way, highway shoulders, scrub brush land and the like.
- these heribicidal compositions otfer the advantage of eompatability with a host of other pesticides and adjuvants, for example, herbicides including the triand tetrachlorophenylacetic acids, the sodium borates and calcium borates, 2,4-D and other herbicidal phenoxy aliphatic acids and esters, simazine and other herbicidal triazines, herbicidal petroleum oils, hexachlorocyclopentadiene, pentach-lor-ophenol, dinitro-o- .alkylphenols, sodium chlorate, sodium trichloroacetate, and sodium 2,2-dichloropropionate, with fungicides such as the metal dimethyldithiocarbamates and ethylenebis- (dithiocarbamates), with insecticides such as benzene hexachloride and chlor
- these herbicdes may be used by themselves or made the subject of liquid or solid formulations ranging from the very simple to the most elegant.
- these compositions may be made the subject of a liquid formulation by diluting, dispersing, dissolving or emulsifying with a surface active adjuvant or combination of these adjuvants in water or organic solvents such as petroleum hydrocarbons, alcohols, ketones, esters, glycols or combination thereof.
- the novel herbicides may be made up as solid formulations of powders, dusts, wettable dusts, granules and pellets using solid diluents such as t-alcs, clays, flours, starches, diatomaceous earths, mica, alkaline earth limes, carbonates and phosphates either finely divided, granular or pelleted in form.
- solid diluents such as t-alcs, clays, flours, starches, diatomaceous earths, mica, alkaline earth limes, carbonates and phosphates either finely divided, granular or pelleted in form.
- the liquid compositions may contain as a conditioning agent one or more surface active agents in amounts sulficient to render the composition readily dispersible in water.
- surface active agents are included wetting agents, dispersing agents, emulsifying agents and the like.
- a satisfactory but not complete list of such agents is set forth in an article in Soap and Chemical Specialties, vol. 31, No. 7, pages 50 to 61; No. 8, pages 48 to 61; No. 9, pages 52 to 67, and No. pages 38 to 67 (1955).
- Other sources of adjuvant materials is set forth in Bulletin E 607 of the Bureau of Entomology and Plant Quarantine of the United States Department of Agriculture.
- a preferred embodiment of this invention is to apply these herbicides as a spray after making them up as a liquid formulation comprised of several times their weight of solvents such as xylene or water with small quantities of an emulsifier or wetting agent such as a commercial polyoxyethylene ether or alkylaryl sulfonate.
- solvents such as xylene or water
- an emulsifier or wetting agent such as a commercial polyoxyethylene ether or alkylaryl sulfonate.
- This type of mixture is diluted or emulsified with water and sprayed on the weed population or onto the soil where weed growth is to be prevented.
- these compositions may be applied as a solid formulation directly to the ground.
- the rate of application cannot be precisely stated due to varying degree of resistance possessed by the weed species and crop, the stage of weed and crop growth, the soil type and climatic conditions, but in general, the rates will be at least one-quarter of a pound of each component per acre and for reasons of cost will seldom exceed one hundred pounds of each component per acre with the preferred range falling Within one-half to fifty pounds per acre.
- the weeds are in an early stage of growth, they being more susceptible, will frequently respond to the rates from one-half to four pounds of each component per acre while older weeds o-r weeds that are to be totally eradicated from ornamental beds or turf may require rates in excess of four pounds per acre.
- Example 1 A representative formulation of the composition of the invention is the following:
- N-(p-chlorophenyl) -N',N'-dimethylurea 40 2,3,5,6-tetrachlorobenzoic acid 40 Attapulgus clay 15 Marasperse (a commercial dispersing agent) 2.5 Sorbit-P (a commercial wetting agent) 2.5
- the ingredients are ground together to pass a three hundred mesh screen, yielding a powder which can be readily dispersed and suspended in water by mild agitation.
- Example 2 A useful formulation of the composition of this invention is as follows:
- Example 3 Similar to Example 2 but with N-(3,4-dichlorophenyl)- N,N-dimethylurea.
- Example 4 The following example illustrates the synergistic effect of the compositions of this invention.
- Example 5 A test area in Niagara County, New York, infested with a rank growth of plantain, teasel, chicory, goldenrod, and wild carrot was treated in late spring with the test chemicals in formulations as described in Examples 1 and 2. In the succeeding fall the plots were inspected, with the following observations:
- a herbicidal composition comprising from one to forty parts by weight of a compound selected from the group consisting of 2,3,5,6-tetrachlorobenzoic acid, the acid chloride of 2,3,5,6-tetrachlorobenzoic acid, 2,3,5,6- tetrachlorobenzamide and the salts of 2,3,5,6-tetrachlorobenzoic acid wherein the cation is selected from the group consisting of metal, ammonium, alkanol ammonium and alkyl substituted ammonium, combined with one to forty parts by weight of a N-phenyl-N',N'-disubstituted urea, wherein the substituent is selected from the group consisting of lower alkyl and phenyl substituted lower alkyl, said components being present in such amount as to exert herbicidal activity.
- composition of claim 1 wherein the urea is N- (p-chlorophenyl)-N',N-dimethylurea.
- composition of claim 2 wherein the ratio of N-(p-chlorophenyl)-N,N'-dimethylurea to 2,3,5,6-tetrachlorobenzoic compound is from four to one to one to four.
- a method for controlling weeds which comprises applying to the locus to be treated from one to forty parts by weight of a compound selected from the group consisting of 2,3,5,6 -tetrachloirobenzdic acid, the acid chloride of '2.,3,5,6 tetrachloroblenzoic acid, 2,3,5,6- tetrachlonobenzamide and the salts of 2,3,5,6-tetrachlorobenzoic acid wherein the cation is selected from the group consisting of metal, ammonium, alkanol ammonium and alkyl substituted ammonium combined with from one to forty parts by weight of an N-phenyl-N'-N'- disubstituted urea wherein the substituent is selected from the group consisting of lower alkyl and phenyl substituted lower alkyl, said components being applied in such amounts as to exert herbicidal activity.
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Description
United States Patent Ofifice 3,298,8l8 Patented Jan. 17, 1967 3,298,818 TETRAHALOBENZOKC AClD-N-PHENYL-N',N- DIALKYLUREA HERBICIDE COMPOSITIONS Jack S. Newcomer, E. Lake Road, Wilson, N.Y. 14172;
Jerome Linder, 522 78th St, Niagara Falls, N.Y. 14304; and Keith J. Smith, 6135 Ridge Road, Lockport, N.Y. 14094 No Drawing. Filed May 15, 1961, er. No. 109,851 4 Claims. (Cl. 71-'2.6)
This application is a continuation-in-part of S.N. 505,- 032, filed April 29, 1955, now US. Patent No. 3,014,965, and S.N. 661,600, filed May 29, 1957, now abandoned.
This invention relates to novel compositions of matter comprising ureas and certain tetrahalogenated aromatic acids and its derivatives useful as herbicides, which exhibit unobvious and enhanced herbicidal acitivity not logically predictable from the individual properties of the components by themselves.
More specifically, this invention describes synergistic herbicidal combinations of N-phenyl-N',N'-dialkylureas and a member of the group selected from 2,3,5.,6-tetrachlorobenzoic acid, the salts of 2,3,5,6-tetrachlorobenzoic acids and the derivatives of 2,3,5,6-tetrachlorobenzoic acid. Suitable salts include those which contain an inorganic or organic cation such as sodium, potassium, calcium, strontium, barium, magnesium, aluminum, iron, cobalt, nickel, zinc, ammonium, mono-, di-, trialkyl and 'alkanol amonium salts. Suitable derivatives include but are not limited to the esters, amides, imides, acid chloride, and anhydrides of 2,3,5,6-tetrachlorobenzoic acid.
Examples of the heribcidal combinations contemplated to be within the purview of this invention are the following:
N-phenyl-N,N-dimethylurea,
N- 3 ,4-dichlorophenyl -N',N'-di.methylurea, N-(p-chlorop-henyl)-N,N-dimethylurea, N-n-butyl-N- 3 ,4-dichlorophenyl) -N-methylurea, N- phenyl-N-(2-hydroxyethyl)urea,
N- 3,4-dichlorophenyl) -N-cyclohexy1 urea, N-(p-chlorophenyl-N'-cycl0hexyl) urea, N-phenyl-N',N'-diisopropylurea,
N- 3 ,4-dichlorophenyl) -N',N-diisopropylurea, N-(p-chlorophenyl)-N,N'-diisopropylurea, N-phenyl-N-benzyl urea,
N-(3,4dichlorophenyl) -N',N-dibenzyl urea,
N- (p-chlorophenyl) -N',N'-dibenzyl urea, N-phenyl-N',N'isopropylurea,
N- 3 ,4-dichlorophenyl -N',N'-isopropyl urea, N-(p-chlorophenyl)-N',N'-isopropyl urea, N-phenyl N,N'-n-butyl urea,
N- 3,4-dichlorophenyl-N'-methyl-N'-n-butyl) urea and N-(p-chlorophenyl)-N,N'-n-butyl urea, combined with the salts, free acid, acid chloride, amide, irnide, anhydride, and esters of 2,3,5,6 tetrachlorobenzoic acid. All of these salts and derivatives of 2,3,5,6-tetrachlorobenzoic acid as well as the acid itself may be considered to some degree herbicidal equivalents, although the acid and its alkali metal, ammonium, and lower alkyl-substituted ammonium salts are preferred because of lower cost and ease of formulation. While all of the above ureaacid and urea-acid derivatives may be considered synergistic, the greatest potentiation has been observed using N- phenyl-N',N-dimethylurea, N (3,4 dichlorophenyl)- N,N-dimethylurea, N-(p-chlorophenyl) N,N'-dimethylurea or N-(3,4-d'ichlorophenyl) -N'-methyl N n-butyl a technical crude.
urea combined with either 2,3,5,6-tetrachlorobenzoic acid or its sodium, potassium, ammonium or lower alkyl substituted ammonium salts. Thus, any and all of these combinations may be considered the preferred embodimenis of this invention.
The synergistic herbicidal combinations of this invention offer several advantages over herbicidal compositions of the prior art. For example, the total herbicidal efiect of these combinations of urea and acid have been found to be greater than the individual herbicidal effect of either component taken additively. This enhancement or potentiation is manifested in several ways, all of which are of practical value to the user. For instance, the rate of application that is needed to control the weed populace is significantly reduced; the phytotoxic effect seems to be accelerated resulting in more rapid kill; there seems to be a longer term regression of the weed populations regrowth, or expressed another way, a longer term sterilization of the soil results; lastly, there appears to be a more pronounced eifect against weeds recalcitrant to the phytot-oxic effect of the individual herbicides. This long term sterilization coup-led with low rates of application make the inventive compositions especially suitable for use on low value land such as rights of way, highway shoulders, scrub brush land and the like.
As additional advantage of the novel compositions of this invention is that they may be used in various grades of purity ranging from the highly purified material to Furthermore, these heribicidal compositions otfer the advantage of eompatability with a host of other pesticides and adjuvants, for example, herbicides including the triand tetrachlorophenylacetic acids, the sodium borates and calcium borates, 2,4-D and other herbicidal phenoxy aliphatic acids and esters, simazine and other herbicidal triazines, herbicidal petroleum oils, hexachlorocyclopentadiene, pentach-lor-ophenol, dinitro-o- .alkylphenols, sodium chlorate, sodium trichloroacetate, and sodium 2,2-dichloropropionate, with fungicides such as the metal dimethyldithiocarbamates and ethylenebis- (dithiocarbamates), with insecticides such as benzene hexachloride and chlordane, with fertilizers such as urea and ammonium nitrate, and various adjuvants and diluents well known to the art. Thus, these herbicdes may be used by themselves or made the subject of liquid or solid formulations ranging from the very simple to the most elegant. For example, if it is desired these compositions may be made the subject of a liquid formulation by diluting, dispersing, dissolving or emulsifying with a surface active adjuvant or combination of these adjuvants in water or organic solvents such as petroleum hydrocarbons, alcohols, ketones, esters, glycols or combination thereof. vOr alternatively, the novel herbicides may be made up as solid formulations of powders, dusts, wettable dusts, granules and pellets using solid diluents such as t-alcs, clays, flours, starches, diatomaceous earths, mica, alkaline earth limes, carbonates and phosphates either finely divided, granular or pelleted in form.
These solid and liquid formulations facilitate handling and application and sometimes enhance herbicidal activity to more than an additive degree.
The liquid compositions, whether solutions or dispersions of the active agents in a liquid solvent and also the wettable powder or dust compositions of this invention may contain as a conditioning agent one or more surface active agents in amounts sulficient to render the composition readily dispersible in water. By the term surface active agents are included wetting agents, dispersing agents, emulsifying agents and the like. A satisfactory but not complete list of such agents is set forth in an article in Soap and Chemical Specialties, vol. 31, No. 7, pages 50 to 61; No. 8, pages 48 to 61; No. 9, pages 52 to 67, and No. pages 38 to 67 (1955). Other sources of adjuvant materials is set forth in Bulletin E 607 of the Bureau of Entomology and Plant Quarantine of the United States Department of Agriculture.
While the manner and method of application of the inventive compositions in varied and largely dependent upon the climatic conditions, crop treated, the weeds to be eradicated, the equipment available and the convenience of the user, a preferred embodiment of this invention is to apply these herbicides as a spray after making them up as a liquid formulation comprised of several times their weight of solvents such as xylene or water with small quantities of an emulsifier or wetting agent such as a commercial polyoxyethylene ether or alkylaryl sulfonate. This type of mixture is diluted or emulsified with water and sprayed on the weed population or onto the soil where weed growth is to be prevented. Or alternatively, these compositions may be applied as a solid formulation directly to the ground.
The rate of application cannot be precisely stated due to varying degree of resistance possessed by the weed species and crop, the stage of weed and crop growth, the soil type and climatic conditions, but in general, the rates will be at least one-quarter of a pound of each component per acre and for reasons of cost will seldom exceed one hundred pounds of each component per acre with the preferred range falling Within one-half to fifty pounds per acre. Where the weeds are in an early stage of growth, they being more susceptible, will frequently respond to the rates from one-half to four pounds of each component per acre while older weeds o-r weeds that are to be totally eradicated from ornamental beds or turf may require rates in excess of four pounds per acre. In those instances where the weed population has been allowed to accumulate unchecked or where mature plants are encountered, applications of up to fifty and even beyond this rate may be required. For eradication of deeplyrooted herbicide-resistant perennial weeds such as field bindweed, rates of ten to one hundred pounds of each component are found best. While the synergism between 2,3,5,6-tetrachlorobenzoic acid and the ureas is manifested at Wide ratios of acid to urea, the greatest synergistic effect has been observed at ratios ranging from 0.1 to ten parts by weight of urea to one part by weight of the acid, salts or derivatives.
The following examples are intended to illustrate the workings of this invention including such facets as the Example 1 A representative formulation of the composition of the invention is the following:
Parts by weight N-(p-chlorophenyl) -N',N'-dimethylurea 40 2,3,5,6-tetrachlorobenzoic acid 40 Attapulgus clay 15 Marasperse (a commercial dispersing agent) 2.5 Sorbit-P (a commercial wetting agent) 2.5
The ingredients are ground together to pass a three hundred mesh screen, yielding a powder which can be readily dispersed and suspended in water by mild agitation.-
Example 2 A useful formulation of the composition of this invention is as follows:
Parts by weight Sodium 2,3,5,6-tetrachlorobenzoa'te 160 N-(p-chloroph-enyl) -N'N'-dimethylurea 8O Attapulgus clay 18 Marasperse 2 The ingredients are ground to make a powder which partially dissolves and partially suspends in water.
Example 3 Similar to Example 2 but with N-(3,4-dichlorophenyl)- N,N-dimethylurea.
Example 4 The following example illustrates the synergistic effect of the compositions of this invention.
A test area in Erie County, New York, infested with quackgrass, chicory, dock, ragweed, plantain, oxalis, foxtail, and bindweed was sprayed with an aqueous suspension of the type described in the foregoing examples. One year later, the treated area was inspected for weed control.
None of the individual urea or acid or acid derivative components acted as soil sterilants at 2.5 to eight pounds per acre. Nor did the degree of weed control given by such low rates of the individual compounds approximate to one-half the control given by the compositions of the invention. Thus it would appear the combinations given above are evidentiary of synergism.
Pounds Per Acre Required To Accomplish Kill Chemical Bindweed Quackgrass Dock Plantain Chicory 1. 2,3,5,6-tctrachlorobeuzamide 45 35 40 30 30 2. Sodium 2,3,5,fi-tetrachlorobenz0ate 25 2O 25 20 20 3. N-(p-ehl0ropheny1)-N,N-dimethyl 25 20 25 2O 20 4. N-phenyl-N,N-dimethyluroa 25 25 25 25 20 5. N-(3,4(lichlorophenyl)-N,N-dimethylurea w 25 2O 20 20 25 6. N-(3,4-dichl0rophenyl)-N-methyl-N- n-butyl urea 30 25 25 25 20 7. Sodium 2,3,5.6-totrachlorobenzoate plus N-(p-ohlorophenyl)-N,N-dimethylurea 3+2. 5 5+2. 5 5+2. 5 5+2. 5 .5+5 2. 5+5 2. 5+5 2. 5 5 8. Sodium 2,3,5,fi-tetrachlorobeuzoate plus N-(p-chlorophenyl)-N,N-dimethylurea git; g+3 7+3 7+3 7+3 7 +7 3+7 3+7 3 7 9. Sodium 2,3,5,G-tetrachlorobeuzoate plus N-phenyl-N,N-dimethylurea 5+5 5+5 5+5 5+5 5+5 10. Sodium 2,3,5,6-tetrachlorobenz0ate plus N-(3,4-dichlor0phenyD-N -methyl-N-nbutyl urea 5+5 5+5 5+5 5+5 5+5 11. Sodium 2,3,5,G-tetrachlorobenzoate plus 1Is -g3ft-dichlorophenyl)-N-methyl-N-n- 7 5+2 5 7 5+ 5 7 5 2 r 7 5+ 5 7 5 9 5 u y urea h .a s,
5 Example 5 A test area in Niagara County, New York, infested with a rank growth of plantain, teasel, chicory, goldenrod, and wild carrot was treated in late spring with the test chemicals in formulations as described in Examples 1 and 2. In the succeeding fall the plots were inspected, with the following observations:
Pounds Per Acre (p-chlr0phel1yl)-N, N-dimethylurea. 11. Sodium 2, 3, 5, 6-tetrachlorobenzoate plus N- pheny1-N-, N -dimethylurea. 5+
12. Sodium 2, 3, 5, G-tetrachlorobenzoate plus N- 7+7 respectively.
(3, 4-dieh1orophenyD-N, N-dimethylurea.
13. Sodium 2, 3, 5, G-tetrachlorobenozoate plus N- 10+10 (3, 4-dichlorophenyl)-N-methyl-N-n-butyl respectively. urea.
14. Sodium 2,3, 5, G-tetrachlorobenzoate 45.
Each of the components above, individually, gave substantially no control of these perennial weeds at rates twice that of the combined rates.
The required rates in this experiment were observed to be generally higher than in the experiment of Example 4. This is understandable in that the weed infestation involved was of much larger establishment, with ranker and more deeply rooted growth. However, since the combinations are much superior than the individual components it would appear as though the increase in activity is caused by synergistic interaction.
The examples of the composition of our invention and methods of preparing and utilizing them, which have been described in the foregoing specification, have been given for purposes of illustration, not limitation. Many other modifications and ramifications will naturally suggest themselves to those skilled in the art, based on the disclosure of our basic discovery. These are intended to be comprehended within the scope of our invention.
We claim:
1. A herbicidal composition comprising from one to forty parts by weight of a compound selected from the group consisting of 2,3,5,6-tetrachlorobenzoic acid, the acid chloride of 2,3,5,6-tetrachlorobenzoic acid, 2,3,5,6- tetrachlorobenzamide and the salts of 2,3,5,6-tetrachlorobenzoic acid wherein the cation is selected from the group consisting of metal, ammonium, alkanol ammonium and alkyl substituted ammonium, combined with one to forty parts by weight of a N-phenyl-N',N'-disubstituted urea, wherein the substituent is selected from the group consisting of lower alkyl and phenyl substituted lower alkyl, said components being present in such amount as to exert herbicidal activity.
2. The composition of claim 1 wherein the urea is N- (p-chlorophenyl)-N',N-dimethylurea.
3. The composition of claim 2 wherein the ratio of N-(p-chlorophenyl)-N,N'-dimethylurea to 2,3,5,6-tetrachlorobenzoic compound is from four to one to one to four.
4. A method for controlling weeds which comprises applying to the locus to be treated from one to forty parts by weight of a compound selected from the group consisting of 2,3,5,6 -tetrachloirobenzdic acid, the acid chloride of '2.,3,5,6 tetrachloroblenzoic acid, 2,3,5,6- tetrachlonobenzamide and the salts of 2,3,5,6-tetrachlorobenzoic acid wherein the cation is selected from the group consisting of metal, ammonium, alkanol ammonium and alkyl substituted ammonium combined with from one to forty parts by weight of an N-phenyl-N'-N'- disubstituted urea wherein the substituent is selected from the group consisting of lower alkyl and phenyl substituted lower alkyl, said components being applied in such amounts as to exert herbicidal activity.
References Cited by the Examiner UNITED STATES PATENTS 2,709,648 5/1955 Ryker et al. 712.6 3,005,694 10/1961 Entemann 7l-2.6 3,014,965 12/1961 Newcomer et al. 7l2.61 3,081,162 3/1963 Tis-chler 712.6 3,125,431 3/1964 Kittila 712.6
LEWIS GOTTS, Primary Examiner.
M. A. BRINDISI, IRVING MARCUS, JULIAN S.
LEVITT, Examiners.
I. O. THOMAS, E. J. MEROS, Assistant Examiners.
Claims (1)
1. A HERBICIDAL COMPOSITION COMPRISING ONE TO FORTY PARTS BY WEIGHT OF A COMPOUND SELECTED FROM THE GROUP CONSISTING OF 2,3,5,6-TETRACHLOROBENZOIC ACID, THE ACID CHLORIDE OF 2,3,5,6-TETRACHLOROBENZOIC ACID, 2,3,5,6TETRACHLOROBENZAMIDE AND THE SALTS OF 2,3,5,6-TETRACHLOROBENZOIC ACID WHEREIN THE CATION IS SELECTED FROM THE GROUP CONSISTING OF METAL, AMMONIUM, ALKANOL AMMONIUM AND ALKYL SUBSTITUTED AMMONIUM, COMBINED WITH ONE TO FORTY PARTS BY WEIGHT OF A N-PHENYL-N'',N''-DISUBSTITUTED UREA, WHEREIN THE SUBSTITUENT IS SELECTED FROM THE GROUP CONSISTING OF LOWER ALKYL AND PHENYL SUBSTITUTED LOWER ALKYL, SAID COMPONENTS BEING PRESENT IN SUCH AMOUNT AS TO EXERT HERBICIDAL ACTIVITY.
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US2709648A (en) * | 1949-12-06 | 1955-05-31 | Du Pont | Herbicidal composition and method employing mixtures of a polychlorophenoxy compound with a phenyl dimethyl urea |
US3005694A (en) * | 1958-06-23 | 1961-10-24 | Du Pont | 2, 3, 5, 6-tetrachlorobenzoic acid and salts thereof and herbicidal method employingsame |
US3014965A (en) * | 1955-04-29 | 1961-12-26 | Hooker Chemical Corp | 2, 3, 5, 6-tetrachlorobenzoic acid amides |
US3081162A (en) * | 1956-11-27 | 1963-03-12 | Heyden Newport Chemical Corp | Controlling bindweed with 2, 3, 6-trichlorobenzoic acid and salts thereof |
US3125431A (en) * | 1959-11-06 | 1964-03-17 | Complex of phenylureas and chloro- |
-
1961
- 1961-05-15 US US109851A patent/US3298818A/en not_active Expired - Lifetime
Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2709648A (en) * | 1949-12-06 | 1955-05-31 | Du Pont | Herbicidal composition and method employing mixtures of a polychlorophenoxy compound with a phenyl dimethyl urea |
US3014965A (en) * | 1955-04-29 | 1961-12-26 | Hooker Chemical Corp | 2, 3, 5, 6-tetrachlorobenzoic acid amides |
US3081162A (en) * | 1956-11-27 | 1963-03-12 | Heyden Newport Chemical Corp | Controlling bindweed with 2, 3, 6-trichlorobenzoic acid and salts thereof |
US3005694A (en) * | 1958-06-23 | 1961-10-24 | Du Pont | 2, 3, 5, 6-tetrachlorobenzoic acid and salts thereof and herbicidal method employingsame |
US3125431A (en) * | 1959-11-06 | 1964-03-17 | Complex of phenylureas and chloro- |
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