USRE32316E - Substituted phenoxybenzoic acids and derivatives thereof - Google Patents
Substituted phenoxybenzoic acids and derivatives thereof Download PDFInfo
- Publication number
- USRE32316E USRE32316E US06/075,369 US7536979A USRE32316E US RE32316 E USRE32316 E US RE32316E US 7536979 A US7536979 A US 7536979A US RE32316 E USRE32316 E US RE32316E
- Authority
- US
- United States
- Prior art keywords
- nitro
- benzoate
- compound
- ammonium
- dichlorophenoxy
- 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
Links
- PKRSYEPBQPFNRB-UHFFFAOYSA-N 2-phenoxybenzoic acid Chemical class OC(=O)C1=CC=CC=C1OC1=CC=CC=C1 PKRSYEPBQPFNRB-UHFFFAOYSA-N 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 33
- -1 amine salts Chemical class 0.000 claims abstract description 15
- 239000004009 herbicide Substances 0.000 claims abstract description 8
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 23
- 238000000034 method Methods 0.000 claims description 18
- 230000002363 herbicidal effect Effects 0.000 claims description 15
- 239000000203 mixture Substances 0.000 claims description 14
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- PAYRUJLWNCNPSJ-UHFFFAOYSA-O phenylazanium Chemical compound [NH3+]C1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-O 0.000 claims description 9
- 229910052708 sodium Inorganic materials 0.000 claims description 8
- 239000011734 sodium Substances 0.000 claims description 8
- 125000003342 alkenyl group Chemical group 0.000 claims description 7
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 6
- 229910052700 potassium Inorganic materials 0.000 claims description 6
- 229910052783 alkali metal Inorganic materials 0.000 claims description 5
- 125000005210 alkyl ammonium group Chemical group 0.000 claims description 5
- 125000001204 arachidyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
- PAFZNILMFXTMIY-UHFFFAOYSA-O cyclohexylammonium Chemical compound [NH3+]C1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-O 0.000 claims description 5
- 150000001340 alkali metals Chemical group 0.000 claims description 4
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 4
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 4
- WGQKYBSKWIADBV-UHFFFAOYSA-O benzylaminium Chemical compound [NH3+]CC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-O 0.000 claims description 4
- 229910052744 lithium Inorganic materials 0.000 claims description 4
- 229910052723 transition metal Inorganic materials 0.000 claims description 4
- IUSYSZLVZMUVDO-UHFFFAOYSA-N 5-(2,4-dichlorophenoxy)-2-nitrobenzoic acid Chemical compound C1=C([N+]([O-])=O)C(C(=O)O)=CC(OC=2C(=CC(Cl)=CC=2)Cl)=C1 IUSYSZLVZMUVDO-UHFFFAOYSA-N 0.000 claims description 3
- 150000001342 alkaline earth metals Chemical class 0.000 claims description 3
- 125000000304 alkynyl group Chemical group 0.000 claims description 3
- 125000005131 dialkylammonium group Chemical group 0.000 claims description 3
- ZRALSGWEFCBTJO-UHFFFAOYSA-O guanidinium Chemical class NC(N)=[NH2+] ZRALSGWEFCBTJO-UHFFFAOYSA-O 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 150000003624 transition metals Chemical class 0.000 claims description 3
- 125000005208 trialkylammonium group Chemical group 0.000 claims description 3
- FAXDZWQIWUSWJH-UHFFFAOYSA-N 3-methoxypropan-1-amine Chemical compound COCCCN FAXDZWQIWUSWJH-UHFFFAOYSA-N 0.000 claims description 2
- 230000008635 plant growth Effects 0.000 claims description 2
- CNCNJLDAXNGLQX-UHFFFAOYSA-N 2-nitro-5-(2,4,6-trichlorophenoxy)benzoic acid Chemical compound C1=C([N+]([O-])=O)C(C(=O)O)=CC(OC=2C(=CC(Cl)=CC=2Cl)Cl)=C1 CNCNJLDAXNGLQX-UHFFFAOYSA-N 0.000 claims 2
- XHSJFKSEQXVALQ-UHFFFAOYSA-N 5-(2,4-dichlorophenoxy)-2-nitrobenzoate;2,2-dimethoxyethylazanium Chemical compound COC(C[NH3+])OC.C1=C([N+]([O-])=O)C(C(=O)[O-])=CC(OC=2C(=CC(Cl)=CC=2)Cl)=C1 XHSJFKSEQXVALQ-UHFFFAOYSA-N 0.000 claims 2
- 125000002511 behenyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 2
- UTNOZPUDCVVZBL-UHFFFAOYSA-N butylazanium;5-(2,4-dichlorophenoxy)-2-nitrobenzoate Chemical compound CCCC[NH3+].C1=C([N+]([O-])=O)C(C(=O)[O-])=CC(OC=2C(=CC(Cl)=CC=2)Cl)=C1 UTNOZPUDCVVZBL-UHFFFAOYSA-N 0.000 claims 2
- BYEJYKXXMSURIM-UHFFFAOYSA-M potassium;5-(2,4-dichlorophenoxy)-2-nitrobenzoate Chemical compound [K+].C1=C([N+]([O-])=O)C(C(=O)[O-])=CC(OC=2C(=CC(Cl)=CC=2)Cl)=C1 BYEJYKXXMSURIM-UHFFFAOYSA-M 0.000 claims 2
- UUPNMPIDODEIGR-UHFFFAOYSA-M sodium;2-nitro-5-(2,4,6-trichlorophenoxy)benzoate Chemical compound [Na+].C1=C([N+]([O-])=O)C(C(=O)[O-])=CC(OC=2C(=CC(Cl)=CC=2Cl)Cl)=C1 UUPNMPIDODEIGR-UHFFFAOYSA-M 0.000 claims 2
- XYGHYVMKXJEPEV-UHFFFAOYSA-N [N+](=O)([O-])C1=C(C(=O)[O-])C=C(C=C1)OC1=C(C=C(C=C1)Cl)Cl.COCCC[NH3+] Chemical compound [N+](=O)([O-])C1=C(C(=O)[O-])C=C(C=C1)OC1=C(C=C(C=C1)Cl)Cl.COCCC[NH3+] XYGHYVMKXJEPEV-UHFFFAOYSA-N 0.000 claims 1
- JFXSDPIRFFWBQJ-UHFFFAOYSA-N cyclohexylazanium;5-(2,4-dichlorophenoxy)-2-nitrobenzoate Chemical compound [NH3+]C1CCCCC1.C1=C([N+]([O-])=O)C(C(=O)[O-])=CC(OC=2C(=CC(Cl)=CC=2)Cl)=C1 JFXSDPIRFFWBQJ-UHFFFAOYSA-N 0.000 claims 1
- XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Chemical compound NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 claims 1
- 150000003839 salts Chemical class 0.000 abstract description 13
- 229910052751 metal Inorganic materials 0.000 abstract description 3
- 239000002184 metal Substances 0.000 abstract description 3
- 235000010233 benzoic acid Nutrition 0.000 abstract description 2
- 150000001559 benzoic acids Chemical class 0.000 abstract description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- XXUJMEYKYHETBZ-UHFFFAOYSA-N ethyl 4-nitrophenyl ethylphosphonate Chemical compound CCOP(=O)(CC)OC1=CC=C([N+]([O-])=O)C=C1 XXUJMEYKYHETBZ-UHFFFAOYSA-N 0.000 description 8
- 239000002253 acid Substances 0.000 description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
- BHAAPTBBJKJZER-UHFFFAOYSA-N p-anisidine Chemical compound COC1=CC=C(N)C=C1 BHAAPTBBJKJZER-UHFFFAOYSA-N 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 5
- 239000007921 spray Substances 0.000 description 5
- 238000011282 treatment Methods 0.000 description 5
- JJYPMNFTHPTTDI-UHFFFAOYSA-N 3-methylaniline Chemical compound CC1=CC=CC(N)=C1 JJYPMNFTHPTTDI-UHFFFAOYSA-N 0.000 description 4
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 4
- NAPSCFZYZVSQHF-UHFFFAOYSA-N dimantine Chemical compound CCCCCCCCCCCCCCCCCCN(C)C NAPSCFZYZVSQHF-UHFFFAOYSA-N 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- NHLUVTZJQOJKCC-UHFFFAOYSA-N n,n-dimethylhexadecan-1-amine Chemical compound CCCCCCCCCCCCCCCCN(C)C NHLUVTZJQOJKCC-UHFFFAOYSA-N 0.000 description 4
- VMPITZXILSNTON-UHFFFAOYSA-N o-anisidine Chemical compound COC1=CC=CC=C1N VMPITZXILSNTON-UHFFFAOYSA-N 0.000 description 4
- RZXMPPFPUUCRFN-UHFFFAOYSA-N p-toluidine Chemical compound CC1=CC=C(N)C=C1 RZXMPPFPUUCRFN-UHFFFAOYSA-N 0.000 description 4
- 229920006395 saturated elastomer Polymers 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 239000003760 tallow Substances 0.000 description 4
- GSEJCLTVZPLZKY-UHFFFAOYSA-O triethanolammonium Chemical compound OCC[NH+](CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-O 0.000 description 4
- 240000006995 Abutilon theophrasti Species 0.000 description 3
- 244000237956 Amaranthus retroflexus Species 0.000 description 3
- 241000196324 Embryophyta Species 0.000 description 3
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 3
- 244000299507 Gossypium hirsutum Species 0.000 description 3
- 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 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 240000008042 Zea mays Species 0.000 description 3
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 3
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 3
- 229910052791 calcium Inorganic materials 0.000 description 3
- 239000011575 calcium Substances 0.000 description 3
- 239000000969 carrier Substances 0.000 description 3
- 229910052802 copper Inorganic materials 0.000 description 3
- 239000010949 copper Substances 0.000 description 3
- 235000005822 corn Nutrition 0.000 description 3
- 125000004122 cyclic group Chemical group 0.000 description 3
- JRBPAEWTRLWTQC-UHFFFAOYSA-N dodecylamine Chemical compound CCCCCCCCCCCCN JRBPAEWTRLWTQC-UHFFFAOYSA-N 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 235000019198 oils Nutrition 0.000 description 3
- 150000003141 primary amines Chemical class 0.000 description 3
- JKANAVGODYYCQF-UHFFFAOYSA-N prop-2-yn-1-amine Chemical compound NCC#C JKANAVGODYYCQF-UHFFFAOYSA-N 0.000 description 3
- 150000003335 secondary amines Chemical class 0.000 description 3
- 239000002689 soil Substances 0.000 description 3
- 241000894007 species Species 0.000 description 3
- 150000003512 tertiary amines Chemical class 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 3
- JYYNAJVZFGKDEQ-UHFFFAOYSA-N 2,4-Dimethylpyridine Chemical compound CC1=CC=NC(C)=C1 JYYNAJVZFGKDEQ-UHFFFAOYSA-N 0.000 description 2
- VUGCBIWQHSRQBZ-UHFFFAOYSA-N 2-methylbut-3-yn-2-amine Chemical compound CC(C)(N)C#C VUGCBIWQHSRQBZ-UHFFFAOYSA-N 0.000 description 2
- KDSNLYIMUZNERS-UHFFFAOYSA-N 2-methylpropanamine Chemical compound CC(C)CN KDSNLYIMUZNERS-UHFFFAOYSA-N 0.000 description 2
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 2
- SDYWXFYBZPNOFX-UHFFFAOYSA-N 3,4-dichloroaniline Chemical compound NC1=CC=C(Cl)C(Cl)=C1 SDYWXFYBZPNOFX-UHFFFAOYSA-N 0.000 description 2
- RNBDLNNJCNFVRQ-UHFFFAOYSA-N 3-(2,4-dichlorophenoxy)-2-nitrobenzoic acid Chemical compound OC(=O)C1=CC=CC(OC=2C(=CC(Cl)=CC=2)Cl)=C1[N+]([O-])=O RNBDLNNJCNFVRQ-UHFFFAOYSA-N 0.000 description 2
- MWVTWFVJZLCBMC-UHFFFAOYSA-N 4,4'-bipyridine Chemical group C1=NC=CC(C=2C=CN=CC=2)=C1 MWVTWFVJZLCBMC-UHFFFAOYSA-N 0.000 description 2
- CXNVOWPRHWWCQR-UHFFFAOYSA-N 4-Chloro-ortho-toluidine Chemical compound CC1=CC(Cl)=CC=C1N CXNVOWPRHWWCQR-UHFFFAOYSA-N 0.000 description 2
- FKNQCJSGGFJEIZ-UHFFFAOYSA-N 4-methylpyridine Chemical compound CC1=CC=NC=C1 FKNQCJSGGFJEIZ-UHFFFAOYSA-N 0.000 description 2
- NTSLROIKFLNUIJ-UHFFFAOYSA-N 5-Ethyl-2-methylpyridine Chemical compound CCC1=CC=C(C)N=C1 NTSLROIKFLNUIJ-UHFFFAOYSA-N 0.000 description 2
- VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical compound NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 description 2
- 241000743987 Alopecurus pratensis Species 0.000 description 2
- 235000013479 Amaranthus retroflexus Nutrition 0.000 description 2
- 235000004135 Amaranthus viridis Nutrition 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical class N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- 235000011293 Brassica napus Nutrition 0.000 description 2
- 240000008100 Brassica rapa Species 0.000 description 2
- 235000000540 Brassica rapa subsp rapa Nutrition 0.000 description 2
- 241000217446 Calystegia sepium Species 0.000 description 2
- 235000009344 Chenopodium album Nutrition 0.000 description 2
- 235000005484 Chenopodium berlandieri Nutrition 0.000 description 2
- 235000009332 Chenopodium rubrum Nutrition 0.000 description 2
- 229920000742 Cotton Polymers 0.000 description 2
- XBPCUCUWBYBCDP-UHFFFAOYSA-N Dicyclohexylamine Chemical compound C1CCCCC1NC1CCCCC1 XBPCUCUWBYBCDP-UHFFFAOYSA-N 0.000 description 2
- 244000152970 Digitaria sanguinalis Species 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 244000058871 Echinochloa crus-galli Species 0.000 description 2
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 2
- 235000003403 Limnocharis flava Nutrition 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methyl-N-phenylamine Natural products CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 240000002439 Sorghum halepense Species 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 150000004982 aromatic amines Chemical class 0.000 description 2
- 229910052788 barium Inorganic materials 0.000 description 2
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
- 235000012343 cottonseed oil Nutrition 0.000 description 2
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 2
- JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 2
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 2
- LIWAQLJGPBVORC-UHFFFAOYSA-N ethylmethylamine Chemical compound CCNC LIWAQLJGPBVORC-UHFFFAOYSA-N 0.000 description 2
- VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 description 2
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 2
- 238000005580 one pot reaction Methods 0.000 description 2
- BHRZNVHARXXAHW-UHFFFAOYSA-N sec-butylamine Chemical compound CCC(C)N BHRZNVHARXXAHW-UHFFFAOYSA-N 0.000 description 2
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- MYFHSAJSGPMFFQ-UHFFFAOYSA-N (3-aminophenyl)-tert-butylcarbamic acid Chemical compound CC(C)(C)N(C(O)=O)C1=CC=CC(N)=C1 MYFHSAJSGPMFFQ-UHFFFAOYSA-N 0.000 description 1
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 1
- WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 description 1
- ZQXIMYREBUZLPM-UHFFFAOYSA-N 1-aminoethanethiol Chemical compound CC(N)S ZQXIMYREBUZLPM-UHFFFAOYSA-N 0.000 description 1
- HXKKHQJGJAFBHI-UHFFFAOYSA-N 1-aminopropan-2-ol Chemical compound CC(O)CN HXKKHQJGJAFBHI-UHFFFAOYSA-N 0.000 description 1
- HILAYQUKKYWPJW-UHFFFAOYSA-N 1-dodecylguanidine Chemical compound CCCCCCCCCCCCN=C(N)N HILAYQUKKYWPJW-UHFFFAOYSA-N 0.000 description 1
- GDKOYYDQISQOMH-UHFFFAOYSA-N 1-ethynylcyclohexan-1-amine Chemical compound C#CC1(N)CCCCC1 GDKOYYDQISQOMH-UHFFFAOYSA-N 0.000 description 1
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 1
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 description 1
- QKWWDTYDYOFRJL-UHFFFAOYSA-N 2,2-dimethoxyethanamine Chemical compound COC(CN)OC QKWWDTYDYOFRJL-UHFFFAOYSA-N 0.000 description 1
- LINPIYWFGCPVIE-UHFFFAOYSA-N 2,4,6-trichlorophenol Chemical compound OC1=C(Cl)C=C(Cl)C=C1Cl LINPIYWFGCPVIE-UHFFFAOYSA-N 0.000 description 1
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- 229910052623 talc Inorganic materials 0.000 description 1
- FAGUFWYHJQFNRV-UHFFFAOYSA-N tetraethylenepentamine Chemical compound NCCNCCNCCNCCN FAGUFWYHJQFNRV-UHFFFAOYSA-N 0.000 description 1
- LXUQDZITPQYMIR-UHFFFAOYSA-N thiourea;urea Chemical compound NC(N)=O.NC(N)=S LXUQDZITPQYMIR-UHFFFAOYSA-N 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- WFLJHDLVVWUGGZ-UHFFFAOYSA-N triacontan-1-amine Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCN WFLJHDLVVWUGGZ-UHFFFAOYSA-N 0.000 description 1
- VPYJNCGUESNPMV-UHFFFAOYSA-N triallylamine Chemical compound C=CCN(CC=C)CC=C VPYJNCGUESNPMV-UHFFFAOYSA-N 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- ZMANZCXQSJIPKH-UHFFFAOYSA-O triethylammonium ion Chemical compound CC[NH+](CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-O 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/49—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups
- C07C205/57—Compounds 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
- C07C205/59—Compounds 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
Definitions
- This invention is concerned with certain phenoxybenzoic acid salts and their use as herbicides.
- This invention provides the method for controlling plant growth that comprises applying an herbicidal amount of an herbicidal compound having the formula: ##STR1## wherein X is halogen, n is 1 to 5, and M is alkali metal (Li, Na, K), alkaline earth metal (Ca, Mg, Ba, Sr), transition metal (e.g.
- the compounds of this invention are readily prepared by the Ullmann ether synthesis reaction between the alkali metal (Na, K) salt of a halophenol and a 5-halo (Cl, Br)-2-nitrobenzoic acid or an ester, amide, or salt thereof.
- the 5-halo-2-nitrobenzoic acid is readily prepared by nitrating a m-halotoluene, followed by oxidation of the methyl group by well-known procedures.
- the salts of this invention are prepared from the halophenoxybenzoic acid, using well known salt forming procedures.
- the salts contemplated herein include metal salts, ammonium salts, and amine salts.
- the metal salts are the alkali metal salts (Li, Na, K); alkaline earth metal salts (Ca, Mg, Ba, etc.); and transition metal salts (Cu, Fe, etc.).
- the amine salts contemplated include salts of primary amines, secondary amines, tertiary amines, aryl amines, and heterocyclic amines.
- the primary amines can have 1-30 carbon atoms and can be saturated or unsaturated straight chain, branched chain, or cyclic.
- Non-limiting examples of primary amines are methylamine; ethylamine; n-propylamine; isopropylamine; n-butylamine; dodecylamine; triacontylamine; allylamine; 2-propynylamine; cyclohexylamine; propargylamine; isobutylamine; sec-butylamine; 2-ethylamine; cyclopropylmethylamine; t-butylamine; 1,1-dimethyl-2-propynylamine; 1,1-diethyl-2-propynlamine, tallow amine (E.G. Armeen I), 2,2-diethyl-2-dimethoxy ethylamine; 1-ethylnylcyclohexylamine and benzylamine.
- the secondary amines can have 2-30 carbon atoms and can be saturated or unsaturated, straight chain, branched chain, or cyclic.
- Non-limiting examples of secondary amines are dimethylamine, diethylamine, dibutylamine, dioctylamine, ditetradecylamine, diallylamine, di-2-hexenylamine, dicyclohexylamine, methylethylamine, methyl cyclohexylamine, diisopropylamine, diisopentylamine, ethyl cyclohexylamine, (3-aminopropyl)alkenylamine wherein the alkenyl group has 16 to 18 carbon atoms; (3-aminopropyl)alkenylamine wherein the alkenyl group has 18, 20 and 22 carbon atoms; and dihydrogenated tallow amine (e.g. Armeen 2HT).
- Armeen 2HT dihydrogenated tallow amine
- the tertiary amines can have 3-30 carbon atoms and can be saturated or unsaturated, straight chain, branched chain, or cyclic.
- Non-limiting examples of tertiary amines are trimethylamine, dimethyl ethylamine, triethylamine, tributylamine, trioctylamine, triallylamine, triisopentylamine, tricyclohexylamine, dimethyl octylamine, n-hexadecyldimethylamine (e.g. Armeen DM16D), n-octadecyldimethylamine (e.g. Armeen DM18D), methyl di-hydrogenated tallowamine (e.g. Armeen M2HT), and methyl di-cocoamine (e.g. Armeen M2C).
- Non-limiting examples of arylamines are aniline; 2-chloroaniline; 3-chloroaniline; 4-chloroaniline; 2-methyl-4-chloroaniline; 2,4-dichloroaniline; 3,4-dichloroaniline; 2,6-dichloro-4-nitroaniline; m-trifluoromethylaniline; isopropylaniline; p-methoxyaniline; N-methoxymethyl-2,6-diethylaniline; ⁇ -naphthylaniline; N-sec-butyl-4-t-butyl-2,6-dinitroaniline; 3-amino-2,5-dichlorobenzoic acid; N,N-dipropyl ⁇ , ⁇ , ⁇ -trifluoro-2,6-dinitro-p-toluidine; 4-bromo-3-chloroaniline;4(4'-chlorophenoxy)aniline; N 3 , N 3 -diethyl-2,
- heterocyclic amines are 3-amino-1,2,4-triazole; 2-chloro-4-ethylamino-6-isopropylamino-s-triazine; pyridine; piperidine; piperazine; morpholine; 4,4'-dipyridyl; 8-hydroxyquinoline; 4-amino-6-t-butyl--(methylthio)-1,2,4-triazine-5(4H)-one; 6-ethoxy-1,2-dihydro-2,2,4-trimethylquinoline; indole; hexahydro-1H-azepine; 4-amino-5-chloro-2-phenyl-3(2H)-pyridazinone; pyrrole; imidazolidine; isoquinoline; 2,4-lutidine; 2-methyl-5-ethylpyridine; 2-dimethyl aminopyridine; ⁇ -picoline; ⁇ -picoline; ⁇ -picoline; quinoline
- Non-limiting examples of other salt-forming amino compounds contemplated are 2-chloroethyl dimethylamine; diethanolamine; quanidine; dodecylguanidine; 3-(4-chloro-phenyl)-1,1-dimethylurea; 3-(3,4-dichlorophenyl)-1,1-dimethylurea; Fenuron; Tandex ⁇ -alanine; methyl glycine; glycinamide; aminoacetonitrile; aminoethanthiol; aminoacetic acid; diethyl ethanolamine; diethylenetriamine; isopropanolamine; diisopropanolamine; triisopropanolamine; ethylenediamine; hexamethylenetetramine; hydrazine; phenothiazine; sulfanilic acid; tetraethylenepentamine; thiourea; urea; triethanolamine; triethylenetetramine; diethanol soyaamine (e.g
- Example 1 The ester of Example 1 was hydrolyzed to the corresponding acid and, using known salt-forming methods, salt compounds within the scope of this invention were prepared.
- A represents a 2-nitro-5-(2',4'-dichlorophenoxy)benzoate group
- B represents a 2-nitro-5-(2',4',6'-trichlorophenoxy) benzoate group
- C represents a 2-nitro-5-(2',4'-dichloro-6'-fluorophenoxy)benzoate
- D represents a 2-nitro-5-(2'-chloro-4'-fluorophenoxy)benzoate
- the compounds of this invention can be applied in various ways to achieve herbicidal action. They can be applied per se, as solids or in vaporized form, but are preferably applied as the toxic components in pesticidal compositions of the compound and a carrier. These compositions are preferably applied directly to the soil and incorporated therewith.
- the compositions can be applied, as granulars or dusts; as liquid sprays, or as gas-propelled sprays and can contain, in addition to a carrier, additives such as emulsifying agents, binding agents, gases compressed to the liquid state, odorants, stabilizers, and the like.
- additives such as emulsifying agents, binding agents, gases compressed to the liquid state, odorants, stabilizers, and the like.
- a wide variety of liquid and solid carriers can be used.
- Non-limiting examples of solid carriers include talc, bentonite, diatomaceous earth, pyrophyllite, fullers earth, gypsum, flours derived from cotton seeds and nut shells, and various natural and synthetic clays having a pH not exceeding about 9.5.
- Non-limiting examples of liquid carriers include water, organic solvents such as alcohols, ketones, amides and esters, mineral oils such as kerosene, light oils, and medium oils and vegetable oils such as cottonseed oil.
- herbicidal application is measured in terms of pounds of herbicide applied per acre.
- the compounds of this invention are effective herbicides when applied in herbicidal amounts, i.e., at rates between about 0.2 pounds and about 10 pounds per acre.
- All crop and weed species are planted individually in 3 inch plastic pots containing potting soil. Four seeds of each of corn, cotton, and snapbeans are seeded to a depth equal to the diameter of the seed. All other species are surface seeded and sprinkled with screened soil in an amount sufficient to cover the seeds. Immediately after planting, all pots are watered by sub-irrigation in greenhouse trays. Pots for the pre-emergence phase are seeded one day before treatment.
- Planting dates for the post-emergence phase are varied so that all the seedlings will reach the desired stage of developments simultaneously.
- the proper stage of seedling development for treatment in the post-emergence phase is as follows:
- Spray applications are made in a hood containing a movable belt and fixed spray nozzle.
- pre-emergence phase For passage through the spray hood, one pot of each species (pre-emergence phase) is placed on the forward half of a wooden flat and one pot of established plants (post-emergence phase) is placed on the rear half of the flat.
- Treatments are moved to the greenhouse after spraying. Watering during the observation period is applied only by subirrigation.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
Metal salts and amine salts of 2-nitro-5-(halophenoxy)benzoic acids comprise a class of compounds that are highly effective pre- and post-emergence herbicides.
Description
This application is a continuation-in-part of copending application Ser. No. 194,479, filed Nov. 1, 1971, now U.S. Pat. No. 3,776,715 which is a division of application Ser. No. 819,412, filed Apr. 25, 1969, now U.S. Pat. No. 3,652,645.
1. Field of the Invention
This invention is concerned with certain phenoxybenzoic acid salts and their use as herbicides.
2. Description of the Prior Art
It has been proposed to use as herbicides 2-methoxybenzoic acids (U.S. Pat. No. 3,013,054) and 4-phenoxy-benzoic acids (French Pat. No. 1,502,538). It is the discovery of this invention, however, that benzoic acids having a phenoxy substituent in the 5-position are very effective herbicides. U.S. Pat. No. 3,475,427 discloses a position isomer of the acids disclosed herein. This isomeric acid and its salts are ineffective as herbicides.
This invention provides the method for controlling plant growth that comprises applying an herbicidal amount of an herbicidal compound having the formula: ##STR1## wherein X is halogen, n is 1 to 5, and M is alkali metal (Li, Na, K), alkaline earth metal (Ca, Mg, Ba, Sr), transition metal (e.g. Cu, Fe), ammonium, alkylammonium (C1 -C30), alkanolammonium (C1 -C3), alkyl (C1 -C30)dialkanol(C2 -C3)ammonium, dioxyalkylene(C2 -C3)alkyl(C1 -C30)-ammonium, dialkylammonium (C1 -C30), trialkylammonium (C1 -C30), alkoxyalkylammonium (C2 14 C6), dialkoxyalkyl ammonium (C3 -C6), aminoalkylammonium (C1 -C30), dialkylaminoalkylammonium (C3 -C8), alkenylammonium (C2 -C22), alkyl(C1 -C30)aminoalkyl(C2 -C6)ammonium, alkenyl(C2 -C30)aminoalkyl(C2 -C6)-ammonium, alkynyl(C3 -C12)ammonium, dialkenylammonium (C4 -C12), cycloalkylammonium (C3 -C6), alkyl(C1 -C30)ammoniumalkyl(C2 -C6)ammonium, benzylammonium, anilinium, substituted anilinium, guanidinium, or heterocyclicammonium (C4 -C6); and an herbicidal composition containing said compound.
The compounds of this invention are readily prepared by the Ullmann ether synthesis reaction between the alkali metal (Na, K) salt of a halophenol and a 5-halo (Cl, Br)-2-nitrobenzoic acid or an ester, amide, or salt thereof. The 5-halo-2-nitrobenzoic acid is readily prepared by nitrating a m-halotoluene, followed by oxidation of the methyl group by well-known procedures. Generally, the salts of this invention are prepared from the halophenoxybenzoic acid, using well known salt forming procedures.
The salts contemplated herein include metal salts, ammonium salts, and amine salts. The metal salts are the alkali metal salts (Li, Na, K); alkaline earth metal salts (Ca, Mg, Ba, etc.); and transition metal salts (Cu, Fe, etc.).
In addition to the salts of ammonia, the amine salts contemplated include salts of primary amines, secondary amines, tertiary amines, aryl amines, and heterocyclic amines. The primary amines can have 1-30 carbon atoms and can be saturated or unsaturated straight chain, branched chain, or cyclic. Non-limiting examples of primary amines are methylamine; ethylamine; n-propylamine; isopropylamine; n-butylamine; dodecylamine; triacontylamine; allylamine; 2-propynylamine; cyclohexylamine; propargylamine; isobutylamine; sec-butylamine; 2-ethylamine; cyclopropylmethylamine; t-butylamine; 1,1-dimethyl-2-propynylamine; 1,1-diethyl-2-propynlamine, tallow amine (E.G. Armeen I), 2,2-diethyl-2-dimethoxy ethylamine; 1-ethylnylcyclohexylamine and benzylamine.
The secondary amines can have 2-30 carbon atoms and can be saturated or unsaturated, straight chain, branched chain, or cyclic. Non-limiting examples of secondary amines are dimethylamine, diethylamine, dibutylamine, dioctylamine, ditetradecylamine, diallylamine, di-2-hexenylamine, dicyclohexylamine, methylethylamine, methyl cyclohexylamine, diisopropylamine, diisopentylamine, ethyl cyclohexylamine, (3-aminopropyl)alkenylamine wherein the alkenyl group has 16 to 18 carbon atoms; (3-aminopropyl)alkenylamine wherein the alkenyl group has 18, 20 and 22 carbon atoms; and dihydrogenated tallow amine (e.g. Armeen 2HT).
The tertiary amines can have 3-30 carbon atoms and can be saturated or unsaturated, straight chain, branched chain, or cyclic. Non-limiting examples of tertiary amines are trimethylamine, dimethyl ethylamine, triethylamine, tributylamine, trioctylamine, triallylamine, triisopentylamine, tricyclohexylamine, dimethyl octylamine, n-hexadecyldimethylamine (e.g. Armeen DM16D), n-octadecyldimethylamine (e.g. Armeen DM18D), methyl di-hydrogenated tallowamine (e.g. Armeen M2HT), and methyl di-cocoamine (e.g. Armeen M2C).
Non-limiting examples of arylamines are aniline; 2-chloroaniline; 3-chloroaniline; 4-chloroaniline; 2-methyl-4-chloroaniline; 2,4-dichloroaniline; 3,4-dichloroaniline; 2,6-dichloro-4-nitroaniline; m-trifluoromethylaniline; isopropylaniline; p-methoxyaniline; N-methoxymethyl-2,6-diethylaniline; α-naphthylaniline; N-sec-butyl-4-t-butyl-2,6-dinitroaniline; 3-amino-2,5-dichlorobenzoic acid; N,N-dipropyl α, α, α-trifluoro-2,6-dinitro-p-toluidine; 4-bromo-3-chloroaniline;4(4'-chlorophenoxy)aniline; N3, N3 -diethyl-2,4-dinitro-6-trifluoromethyl-m-phenylenediamine; p-dimethylaminoaniline; diphenylamine; p-bromoaniline; m-aminophenyl-t-butylcarbamate; o-phenylenediamine; m-phenylenediamine; 4-dimethylamino-3,5-dimethylphenol; 4-methylsulfonyl)-2,6-dinitro-N,N-dipropylaniline; 3,5-dinitro-N,N-dipropylsulfanilamide; N-sec-butyl-2,6-dinitroaniline; m-toluidine; p-toluidine; m-t-butylaniline; o-anisidine; p-anisidine; dimethylaniline; o-nitroaniline; p-nitroaniline; and 4,4'-oxydianiline.
Non-limiting examples of heterocyclic amines are 3-amino-1,2,4-triazole; 2-chloro-4-ethylamino-6-isopropylamino-s-triazine; pyridine; piperidine; piperazine; morpholine; 4,4'-dipyridyl; 8-hydroxyquinoline; 4-amino-6-t-butyl--(methylthio)-1,2,4-triazine-5(4H)-one; 6-ethoxy-1,2-dihydro-2,2,4-trimethylquinoline; indole; hexahydro-1H-azepine; 4-amino-5-chloro-2-phenyl-3(2H)-pyridazinone; pyrrole; imidazolidine; isoquinoline; 2,4-lutidine; 2-methyl-5-ethylpyridine; 2-dimethyl aminopyridine; α-picoline; β-picoline; γ-picoline; quinoline; and 4,4'-dipyridine.
Non-limiting examples of other salt-forming amino compounds contemplated are 2-chloroethyl dimethylamine; diethanolamine; quanidine; dodecylguanidine; 3-(4-chloro-phenyl)-1,1-dimethylurea; 3-(3,4-dichlorophenyl)-1,1-dimethylurea; Fenuron; Tandex β-alanine; methyl glycine; glycinamide; aminoacetonitrile; aminoethanthiol; aminoacetic acid; diethyl ethanolamine; diethylenetriamine; isopropanolamine; diisopropanolamine; triisopropanolamine; ethylenediamine; hexamethylenetetramine; hydrazine; phenothiazine; sulfanilic acid; tetraethylenepentamine; thiourea; urea; triethanolamine; triethylenetetramine; diethanol soyaamine (e.g. Ethomeen S-12) and didacaoxyethyene soyaamine (e.g. Ethomeen S-20).
The following example illustrates the preparation of a typical compound of this invention and demonstrates a method for product recovery.
A stirred solution of methyl 5-chloro-2-nitrobenzoate (17.0 g., 0.079 mole) and the potassium salt of 2,4,6-trichlorophenol (18.6 g., 0.079 mole) in dimethyl sulfoxide (100 ml.) was heated at 90° for 17 hours. The cooled reaction mixture was diluted with water (500 ml.) and then extracted with ether (3×100 ml.). The combined ether fractions were washed with 10% sodium hydroxide solution (2×30 ml.) and then with a saturated aqueous sodium chloride solution. The ether solution was dried (Na2 SO4) and the solvent evaporated to give a dark oil. Two crystallizations (petroleum ether) gave 1.91 g. of a pale yellow solid, m.p. 101°-103°.
Example 1
I.R. (numol): c=o 1723, c--o 1240, and 1260 cm-1
NMR (CDCl3): methyl 3.91 ppm (3H), quartet
6.96 ppm (1H, J=2.5 and 8 c.p.s.), doublet
7.05 ppm (1H, J=2.5 c.p.s.), broad singlet
7.05 ppm (2H), and doublet 8.01 ppm (1H, J=8 c.p.s.).
The ester of Example 1 was hydrolyzed to the corresponding acid and, using known salt-forming methods, salt compounds within the scope of this invention were prepared.
These compounds are identified below, wherein "A" represents a 2-nitro-5-(2',4'-dichlorophenoxy)benzoate group, "B" represents a 2-nitro-5-(2',4',6'-trichlorophenoxy) benzoate group, "C" represents a 2-nitro-5-(2',4'-dichloro-6'-fluorophenoxy)benzoate and "D" represents a 2-nitro-5-(2'-chloro-4'-fluorophenoxy)benzoate;
2. sodium B.
3. ethanolammonium B.
4. dimethylammonium B.
5. potassium A.
6. arachidyl (90%)-behenyl (10%) ammonium A.
7. arachidyl (90%)-behenyl(10%)aminopropylammonium A.
8. arachidyl (90%)-behenyl(10%)ammoniumpropylammonium bis-[A].
9. isobutylammonium A.
10. n-butylammonium A.
11. methoxypropylammonium A.
12. copper bis-[A].
13. 2,2-dimethoxyethylammonium A.
14. t-butylammonium A.
15. benzylammonium A.
16. allylammonium A.
17. diallyammonium A.
18. ethanolammonium A.
19. 3-dimethylaminopropylammonium A.
20. cyclohexylammonium A.
21. di-n-butylammonium A.
22. N,N-dimethyl-3-(4-methyl-3-cyclohexen-1-yl)butylammonium A.
23. 4-[3-(4-methyl-3-cyclohexen-1-yl)butyl]morpholium A.
24. N,N-dimethyl-3,3-dimethyl-2-norbornylethylammonium A.
29. calcium A.
30. n-propylammonium A.
31. 4(4'-aminophenoxy)anilinium A.
32. 4(4'-phenoxyammonium)anilinium A.
33. 2-propynylammonium A.
34. ammonium A.
35. diethanolammonium A.
36. triethanolammonium A.
37. methylammonium A.
38. trimethylammonium A.
39. isopropylammonium A.
40. sec-butylammonium A.
41. 2-dimethylaminopyridine A.
42. piperidine A.
43. morpholine A.
44. ethylammonium A.
45. diethylammonium A.
46. triethylammonium A.
47. p-methoxyanilinium A.
48. alkenyl(C16 -C18)aminopropylammonium A.
49. alkenyl(C18 -C20)aminopropylammonium A.
50. o-methoxyanilinium A.
51. m-methoxyanilinium A.
52. m-toluidine A.
53. p-toluidine A.
54. guanidine A.
55. anilinium A.
56. di(cyclohexyl)ammonium A.
57. 3,4-dichloroanilinium A.
58. m-chloroanilinium A.
59. p-chloroanilinium A.
60. isopropanolammonium A.
61. diisopropylammonium A.
62. 1,1-dimethyl-2-propynylammonium A.
63. 1,1-diethyl-2-propynylammonium A.
64. 1-ethynylcyclohexylammonium A.
65. n-dodecylaminea A. a=Armeen 12D
66. di(hydrogenated tallow)amineb A. b=Armeen 2HT
67. n-hexadecyldimethylaminec A. c=Armeen DM16D
68. n-octadecyldimethylamined A. d=Armeen DM18D
69. methyl di(hydrogenated tallow)aminee A. e=Armeen M2HT
70. methyl di-cocoaminef A. f=Armeen M2C
71. diethanol soyaamineg A. g=Ethomeen S-12
72. di(decaoxyethylene)soyaamineh A. h=Ethomeen S-20
73. 4,4'-dipyridinium A.
74. pyridinium A.
75. triisopropanolammonium A.
76. tallowaminei A. i=Armeen T
77. diethanolammonium C.
78. triethanolammonium C.
79. p-methoxyanilinium C.
80. ethanolammonium C.
81. sodium C.
82. ammonium C.
83. cyclohexylammonium C.
84. morpholine C.
85. o-methoxyanilinium C.
86. diethanolammonium B.
87. triethanolammonium B.
88. p-methoxyanilinium B.
89. cyclohexylammonium B.
90. morpholine B.
91. o-methoxyanilinium B.
92. diethanolammonium D.
93. triethanolammonium D.
94. p-methoxyanilinium D.
95. ethanolammonium D.
96. sodium D.
97. ammonium D.
98. cyclohexylammonium D.
99. morpholine D.
100. o-methoxyanilium D.
For comparison, a position isomer of the acids used to form the salts of this invention was prepared, as described in U.S. Pat. No. 3,475,427. Salts of this isomeric acid were prepared by known salt-forming methods. These compounds are:
(25) 2-nitro-3-(2',4'-dichlorophenoxy)benzoic acid.
(26) ethanolammonium 2-nitro-3-(2',4'-dichlorophenoxy)benzoate.
(27) n-propylammonium 2-nitro-3-(2',4'-dichlorophenoxy)benzoate.
(28) potassium 2-nitro-3-(2',4'-dichlorophenoxy)benzoate.
The compounds of this invention can be applied in various ways to achieve herbicidal action. They can be applied per se, as solids or in vaporized form, but are preferably applied as the toxic components in pesticidal compositions of the compound and a carrier. These compositions are preferably applied directly to the soil and incorporated therewith. The compositions can be applied, as granulars or dusts; as liquid sprays, or as gas-propelled sprays and can contain, in addition to a carrier, additives such as emulsifying agents, binding agents, gases compressed to the liquid state, odorants, stabilizers, and the like. A wide variety of liquid and solid carriers can be used. Non-limiting examples of solid carriers include talc, bentonite, diatomaceous earth, pyrophyllite, fullers earth, gypsum, flours derived from cotton seeds and nut shells, and various natural and synthetic clays having a pH not exceeding about 9.5. Non-limiting examples of liquid carriers include water, organic solvents such as alcohols, ketones, amides and esters, mineral oils such as kerosene, light oils, and medium oils and vegetable oils such as cottonseed oil.
In practice, herbicidal application is measured in terms of pounds of herbicide applied per acre. The compounds of this invention are effective herbicides when applied in herbicidal amounts, i.e., at rates between about 0.2 pounds and about 10 pounds per acre.
______________________________________
Crabgrass Digitaria sanguinalis
Yellow foxtail grass
Setaria glauca
Johnson grass Sorgum Halepense
Barnyard grass Echinochloa crus-galli
Amaranth pigweed Amaranthus retroflexus
Field bindweed Convoluvulus arvensis
Velvet leaf Abutilon theophrasti
Turnip Brassica sp.
Cotton Gossypium hirsutum var.
DPL smooth leaf
Corn Zea Mays var. Golden
Bantam
Bean Phaseolus vulgaris var.
Black Valentine
______________________________________
All crop and weed species are planted individually in 3 inch plastic pots containing potting soil. Four seeds of each of corn, cotton, and snapbeans are seeded to a depth equal to the diameter of the seed. All other species are surface seeded and sprinkled with screened soil in an amount sufficient to cover the seeds. Immediately after planting, all pots are watered by sub-irrigation in greenhouse trays. Pots for the pre-emergence phase are seeded one day before treatment.
Planting dates for the post-emergence phase are varied so that all the seedlings will reach the desired stage of developments simultaneously. The proper stage of seedling development for treatment in the post-emergence phase is as follows:
______________________________________
GRASSES: 2 inches in height
PIGWEED, BINDWEED, 1 or 2 true leaves visible
VELVET LEAF & TURNIPS:
above cotyledons
COTTON: first true leaf 1 inch in
length; expanded cotyledons
CORN: 3 inches-4 inches in height
BEANS: primary leaves expanded;
growing point at primary
leaf node.
______________________________________
Spray applications are made in a hood containing a movable belt and fixed spray nozzle. For passage through the spray hood, one pot of each species (pre-emergence phase) is placed on the forward half of a wooden flat and one pot of established plants (post-emergence phase) is placed on the rear half of the flat. Treatments are moved to the greenhouse after spraying. Watering during the observation period is applied only by subirrigation.
Compounds are screened initially at a rate of application equivalent to four to eight pounds per acre. Two weeks after treatment the pre- and post-emergence percent injury is visually rated. Subsequent testing can be carried out at 2,1 and 0.5 pounds per acre.
Herbicidal testing of the compounds of Examples 2 through 24 and 30 through 100 and the isomeric compounds showed the results set forth in Table I. The plants are tabulated using the following abbreviations:
TABLE I
__________________________________________________________________________
Compound
Dosage
Pre-/Post-Emergence
Ex. No.
Lbs./Acre
CG YF JG BG PW BW VL TP CT CN BN
__________________________________________________________________________
2 8 50/80 --/--
30/60
40/60
--/--
--/--
--/--
90/100
50/100
0/40
50/100
3 8 20/30 --/40
30/40
30/30
100/--
--/--
--/--
90/100
50/100
0/40
80/70
4 --/-- --/--
--/--
--/--
--/100
--/--
--/--
--/100
--/-- --/--
--/--
2 --/-- --/--
--/--
--/--
100/100
--/--
--/--
90/100
--/-- --/--
--/--
4 4 0/30 --/--
0/40
0/--
0/60
--/--
--/--
0/50
0/70 0/100
100/60
4 0/100
--/--
0/--
0/--
0/--
0/--
70/--
90/100
0/100
0/--
0/80
2 0/10 --/--
0/--
0/--
0/--
0/--
40/--
70/90
0/100
0/--
0/40
5 6 0/20 --/--
0/--
0/--
--/--
--/--
--/--
100/100
30/100
0/--
30/100
1 20/20 --/--
0/--
0/--
--/--
--/--
--/--
100/90
0/20 0/--
0/90
6 2 0/0 --/--
0/--
60/--
100/--
--/--
--/--
100/100
0/90 0/--
0/90
1 0/0 --/--
0/--
20/--
--/--
0/--
40/--
80/100
20/100
0/--
0/0
0.5 0/20 --/--
20/--
0/--
--/--
50/--
90/--
70/90
30/70 30/--
0/20
7 2 0/0 --/--
0/--
60/--
100/--
--/--
--/--
90/100
0/80 0/--
0/0
1 20/0 --/--
90/--
20/--
--/--
70/--
80/--
70/90
0/70 30/--
0/30
0.5 30/20 --/--
0/--
30/--
--/--
60/--
50/--
70/80
40/50 0/--
0/20
8 2 0/0 --/--
0/--
40/--
100/--
--/--
--/--
90/90
0/30 0/--
0/50
1 0/30 --/--
0/--
30/--
--/--
70/--
60/--
90/90
50/100
0/--
0/50
0.5 20/20 --/--
0/--
0/--
--/--
50/--
50/--
80/100
80/90 0/--
30/30
9 2 0/0 --/--
0/--
70/--
--/--
40/--
100/--
100/100
40/90 0/--
0/90
10 2 20/20 --/--
0/--
50/--
--/--
90/--
100/--
100/80
100/100
20/--
0/50
11 2 20/0 --/--
40/--
50/--
--/--
100/--
100/--
100/100
100/100
0/--
20/70
12 10 0/20 --/--
0/--
0/--
90/--
--/--
--/--
100/90
40/30 20/--
--/--
13 2 0/0 --/--
50/--
50/--
--/--
90/--
20/--
100/90
30/100
0/--
0/--
14 2 20/0 --/--
40/--
20/--
--/--
30/--
20/--
100/90
0/100
30/0
0/--
15 2 0/0 --/--
0/--
30/--
--/--
40/--
20/--
100/100
50/100
0/--
0/--
16 2 30/0 --/--
0/--
20/--
--/--
80/--
20/--
100/70
100/100
0/--
0/--
17 2 0/20 --/--
50/--
30/--
--/--
90/--
20/--
80/80
30/100
0/--
0/--
18 2 30/20 --/--
0/--
0/--
--/--
30/--
20/--
90/100
100/100
0/--
0/--
19 2 20/0 --/--
70/--
20/--
--/--
50/--
20/--
100/100
0/40 0/--
20/--
20 2 0/0 --/--
40/--
0/--
--/--
60/--
30/--
100/80
0/100
20/--
0/--
21 2 0/0 --/--
30/--
20/--
--/--
50/--
20/--
100/100
50/100
0/--
0/--
22 2 0/0 --/--
40/--
0/--
--/--
80/--
30/--
90/100
0/100
0/--
0/--
23 2 0/20 --/--
30/--
0/--
--/--
70/--
20/--
60/60
0/20 0/--
0/--
24 2 0/0 --/--
20/--
0/--
--/--
70/--
20/--
60/90
0/100
20/--
0/--
25 4 0/0 --/--
0/--
30/--
--/--
20/--
0/--
0/0 0/0 0/--
0/0
26 4 0/0 --/--
0/--
0/--
--/--
0/--
0/--
0/0 0/0 20/--
0/0
27 4 0/0 --/--
20/--
0/--
--/--
0/--
0/--
0/20
0/0 0/--
0/0
28 4 40/0 --/--
0/--
60/--
--/--
20/--
0/--
0/0 20/0 20/--
0/0
29 10 10/10 --/--
10/--
10/--
--/--
100/--
80/--
100/100
10/70 10/--
10/60
30 2 0/0 --/--
0/--
0/--
--/--
100/--
40/--
90/90
0/100
0/--
30/0
31 2 0/0 --/--
0/--
0/--
--/--
30/--
50/--
100/80
90/40 0/--
0/0
32 2 0/0 --/--
0/--
0/--
--/--
40/--
70/--
90/90
30/40 0/--
0/0
33 2 0/0 --/--
0/--
0/--
--/--
30/--
90/--
100/--
0/30 0/--
0/20
34 2 0/0 --/--
0/--
0/--
--/--
0/--
80/--
90/100
0/60 0/--
0/100
35 1 0/20 --/--
0/--
0/--
--/--
0/--
40/--
70/90
0/70 0/--
0/100
36 1 0/0 --/--
0/0 0/--
--/--
0/--
30/--
60/90
0/60 0/--
0/100
37 1 0/0 --/--
20/--
0/--
--/--
40/--
60/--
70/90
0/100
0/--
0/100
38 1 0/0 --/--
0/--
0/--
--/--
0/--
50/--
70/90
0/90 30/--
0/100
39 1 0/0 --/--
0/--
0/--
--/--
50/--
30/--
70/100
0/100
0/--
0/100
40 1 0/30 --/--
0/--
0/--
--/--
0/--
30/--
80/100
0/100
0/--
0/100
41 1 0/30 --/--
0/--
0/--
--/--
50/--
80/--
90/100
0/100
0/--
0/100
42 2 20/0 --/--
0/--
0/--
--/--
50/--
80/--
90/100
0/100
0/--
0/100
43 2 0/0 --/--
0/--
0/--
--/--
60/--
90/--
90/90
0/90 30/--
0/90
44 1 0/0 --/--
0/--
0/--
--/--
0/--
60/--
80/100
0/100
0/--
0/100
45 1 0/0 --/--
0/--
0/--
--/--
0/--
50/--
70/90
20/100
0/--
0/100
46 1 0/0 --/--
0/--
0/--
--/--
40/--
60/--
90/90
0/100
0/--
0/100
47 1 0/0 --/--
0/--
0/--
--/--
0/--
60/--
90/90
0/20 20/--
0/30
48 1 0/0 --/--
0/--
0/--
--/--
0/--
60/--
70/90
0/40 0/--
0/0
49 1 0/0 --/--
0/--
0/--
--/--
0/--
50/--
50/100
0/40 0/--
0/70
50 1 0/0 --/--
0/--
0/--
--/--
80/--
90/--
100/90
0/100
0/--
0/100
51 1 0/0 --/--
0/--
0/--
--/--
80/--
80/--
90/90
0/90 0/--
0/90
52 1 0/0 --/--
0/--
0/--
--/--
50/--
80/--
100/90
30/90 40/--
0/90
53 1 0/0 -- /--
0/--
0/--
--/--
30/--
80/--
90/100
0/90 0/--
0/90
54 1 0/0 --/--
0/--
0/--
--/--
0/--
30/--
70/90
0/20 30/--
0/20
55 1 0/0 --/--
0/--
0/--
--/--
0/--
60/--
90/90
20/20 30/--
0/30
56 1 40/0 --/--
0/--
0/--
--/--
0/--
40/--
90/70
0/80 0/--
0/40
57 1 0/0 --/--
0/--
0/--
--/--
50/--
80/--
100/90
0/90 30/--
0/100
58 1 0/0 --/--
0/--
0/--
--/--
100/--
80/--
90/90
30/100
0/--
0/100
59 1 0/0 --/--
0/--
0/--
--/--
90/--
90/--
90/70
0/90 0/--
0/30
60 1 0/0 --/--
0/--
0/--
--/--
50/--
60/--
80/100
0/90 0/--
0/100
61 1 0/0 --/--
0/--
0/--
--/--
30/--
0/--
100/90
0/90 0/--
0/100
62 1 0/0 --/--
0/--
0/--
--/--
0/--
60/--
90/90
0/50 0/--
0/90
63 1 0/0 --/--
0/--
0/--
--/--
0/--
50/--
80/90
0/20 0/--
0/100
64 1 0/0 --/--
0/--
0/--
--/--
30/--
50/--
90/90
20/40 0/--
0/100
65 1 0/0 --/--
20/--
0/--
--/--
40/--
50/--
90/90
50/60 0/--
0/50
66 1 0/0 --/--
0/--
0/--
--/--
0/--
0/--
20/50
40/-- 0/--
0/0
67 1 0/30 --/--
0/--
0/--
--/--
0/--
30/--
90/90
20/50 0/--
0/100
68 1 0/0 --/--
0/--
0/--
--/--
0/--
60/--
70/90
0/30 0/--
0/90
69 1 0/0 --/--
0/--
0/--
--/--
0/--
30/--
70/90
0/90 30/--
0/100
70 1 0/0 --/--
0/--
0/--
--/--
0/--
50/--
70/90
0/90 0/--
0/100
71 1 0/0 --/--
0/--
0/--
--/--
30/--
40/--
60/90
0/60 0/--
0/100
72 1 0/0 --/--
0/--
0/--
--/--
40/--
30/--
50/90
0/50 0/--
0/100
73 1 0/0 --/--
0/--
0/--
--/--
0/--
50/--
90/90
0/90 0/--
0/90
74 1 0/0 --/--
0/--
0/--
--/--
0/--
80/--
90/90
30/70 0/--
0/100
75 1 0/0 --/--
0/--
0/--
--/--
0/--
40/--
40/100
0/90 0/--
0/100
76 1 0/0 --/--
0/--
0/--
--/--
0/--
50/--
60/100
30/80 0/--
0/100
77 1 0/20 --/--
0/--
0/--
--/--
50/--
60/--
90/100
20/40 0/--
0/40
78 1 0/20 --/--
20/--
0/--
--/--
20/--
50/--
90/100
20/50 0/--
0/30
79 1 0/0 --/--
0/--
0/--
--/--
30/--
80/--
90/100
0/90 0/--
0/0
80 1 0/0 --/--
0/--
0/--
--/--
0/--
90/--
90/90
0/100
0/--
0/50
81 1 0/30 --/--
0/--
0/--
--/--
20/--
70/--
80/90
0/100
0/--
0/30
82 1 0/-- --/--
0/--
0/--
--/--
20/--
90/--
90/--
0/-- 0/--
0/--
83 1 30/20 --/--
20/--
0/--
--/--
100/--
70/--
100/100
20/100
0/--
0/30
84 1 0/20 --/--
0/--
0/--
--/--
50/--
100/--
100/100
20/50 0/--
0/50
85 1 0/0 --/--
0/--
0/--
--/--
60/--
90/--
100/100
0/40 0/--
0/30
86 1 0/0 --/--
0/--
0/--
--/--
0/--
20/--
90/80
0/20 0/--
0/0
87 1 0/0 --/--
0/--
0/--
--/--
0/--
30/--
80/80
0/20 0/--
0/0
88 1 0/0 --/--
0/--
0/--
--/--
0/--
60/--
80/20
20/20 0/--
20/--
89 1 0/0 --/--
0/--
0/--
--/--
0/--
20/--
60/100
0/30 0/--
0/40
90 1 0/0 --/--
0/--
0/--
--/--
20/--
80/--
100/90
20/30 30/--
0/40
91 1 0/0 --/--
0/--
0/--
--/--
40/--
70/--
90/90
0/30 0/--
0/20
92 1 0/0 --/--
0/--
0/--
--/--
0/--
30/--
30/50
0/0 0/--
0/90
93 1 0/20 --/--
0/--
0/--
--/--
0/--
30/--
0/60
0/0 0/--
0/80
94 1 0/20 --/--
0/--
0/--
--/--
0/--
30/--
20/90
0/60 0/--
0/100
95 1 0/0 --/--
0/--
0/--
--/--
0/--
80/--
70/60
0/90 0/--
0/90
96 1 0/0 --/--
0/--
0/--
--/--
0/--
60/--
60/50
0/40 0/--
0/80
97 1 0/0 --/--
20/--
0/--
--/--
0/--
40/--
60/40
0/30 0/--
0/90
98 1 0/0 --/--
0/--
0/--
--/--
0/--
40/--
40/70
20/90 0/--
0/60
99 1 0/0 --/--
0/--
0/--
--/--
0/--
70/--
90/70
0/100
0/--
0/100
100 1 0/0 --/--
0/--
0/--
--/--
30/--
70/--
80/80
0/80 0/--
0/100
__________________________________________________________________________
Crabgrass CG
Yellow foxtail grass
YF
Johnson grass
JG
Barnyard grass
BG
Pigweed PW
Bindweed BW
Velvet leaf
VL
Turnip TP
Cotton CT
Corn CN
Bean BN
Although the present invention has been described with preferred embodiments, it is to be understood that modifications and variations may be resorted to, without departing from the spirit and scope of this invention, as those skilled in the art will readily understand. Such modifications and variations are considered to be within the purview and scope of the appended claims.
Claims (8)
1. The method for controlling plant growth that comprises applying an herbicidal amount of an herbicidal compound having the formula: ##STR2## wherein X is halogen, n is 1 to 5, and M is alkali metal (Li, Na, K), .[.alkaline earth metal, a transition metal, ammonium, alkylammonium (C1 -C30), alkanolammonium (C1 -C3), alkyl (C1 -C30) dialkanol (C2 -C3) ammonium, dioxyalkylene (C2 -C3) alkyl (C1 -C30)ammonium, dialkylammonium (C1 -C30), trialkylammonium (C1 -C30), alkoxyalkylammonium (C2 -C6) dialkoxyalkylammonium (C3 -C6), aminoalkylammonium (C1 -C30), dialkylaminoalkylammonium (C3 -C8), alkenylammonium (C2 -C22), alkyl (C1 -C30 aminoalkyl (C2 -C6) ammonium, alkenyl (C2 -C30) aminoalkyl (C2 -C6) ammonium, alkynyl (C3 -C12) ammonium dialkenylammonium (C4 -C12), cycloalkylammonium (C3 -C6), alkyl (C1 -C30) ammonium alkyl (C2 -C6) ammonium, benzylammonium, anilinium, substituted anilinium, guanidinium or heterocyclicammonium (C.sub. 4 -C6)..]. .Iadd.alkylammonium (C1 -C4), or alkanolammonium (C1 -C3). .Iaddend. .[.
2. The method of claim 1, wherein said compound is butylammonium 2-nitro-5-(2',4'-dichlorophenoxy)benzoate..]. .[.3. The method of claim 1, wherein said compound is methoxypropylammonium 2-nitro-5-(2',4'-dichlorophenoxy) benzoate..]. .[.4. The method of claim 1, wherein said compound is cyclohexylammonium 2-nitro-5-(2',4'-dichlorophenoxy) benzoate..]. .[.5. The method of claim 1, wherein said compound is 2,2-dimethoxyethylammonium 2-nitro-5-(2',4'-dichlorophenoxy)benzoate..]. .[.6. The method of claim 1, wherein said compound is allylammonium 2-nitro-5-(2',4'-dichlorophenoxy)benzoate..]. .[.7. The method of claim 1, wherein said compound is arachidyl (90%) behenyl (10%) aminopropylammonium 2-nitro-5-(2',4'-dichlorophenoxy)benzoate..]. .[.8. The method of claim 1, wherein said compound is potassium
2-nitro-5-(2',4'-dichlorophenoxy)benzoate..]. 9. The method of claim 1, wherein said compund is ethanolammonium
2-nitro-5-(2',4',6'-trichlorophenoxy)benzoate. 10. The method of claim 1, wherein said compound is sodium
2-nitro-5-(2',4',6'-trichlorophenoxy)benzoate. 11. An herbicidal composition comprising a carrier for an herbicide and an herbicidal amount of an herbicidal compound having the formula: ##STR3## wherein X is halogen, n is 1 to 5, and M is alkali metal (Li, Na, K), .[.alkaline earth metal, a transition metal, ammonium, alkylammonium (C1 4 -C30), alkanolammonium (C1 -C3), alkyl (C1 -C30), dialkanol (C2 -C3) ammonium, dioxyalkylene (C2 -C3) alkyl (C1 -C30)ammonium, dialkylammonium (C1 -C30), trialkylammonium (C1 -C30), alkoxyalkylammonium (C2 -C6) dialkoxyalkylammonium (C3 -C6), aminoalkylammonium (C1 -C30), dialkylaminoalkylammonium (C3 -C8), alkenylammonium (C2 -C22), alkyl (C1 -C30) aminoalkyl (C2 -C6) ammonium, alkenyl (C2 -C30) aminoalkyl (C2 -C6) ammonium, alkynyl (C3 -C12)ammonium, dialkenylammonium (C4 -C12), cycloalkylammonium (C3 -C6), alkyl (C1 -C30) ammonium alkyl (C2 -C6) ammonium, benzylammonium, anilinium, substituted anilinium, guanidinium or heterocyclicammonium (C4 -C6)..]. .Iadd.alkylammonium (C1 -C4), or alkanolammonium (C1
-C3). .Iaddend. .[.12. The composition of claim 11, wherein said compound is butylammonium 2-nitro-5-(2',4'-dichlorophenoxy)benzoate..]. .[.13. The composition of claim 11, wherein said compound is methoxypropylammonium 2-nitro-5-(2',4'-dichlorophenoxy)benzoate..]. .[.14. The composition of claim 11, wherein said compound is cyclohexylammonium 2-nitro-5-(2',4'-dichlorophenoxy)benzoate.]. .[.15. The composition of claim 11, wherein said compound is 2,2-dimethoxyethylammonium 2-nitro-5-(2',4'-dichlorophenoxy)benzoate..]. .[.16. The composition of claim 11, wherein said compound is allylammonium 2-nitro-5-(2',4'-dichlorophenoxy)benzoate..]. .[.17. The composition of claim 11, wherein said compound is arachidyl (90% ) behenyl (10%) aminopropylammonium 2-nitro-5-(2',4'-dichlorophenoxy benzoate..]. .[.18. The composition of claim 11, wherein said compound is potassium
2-nitro-5-(2',4'-dichlorophenoxy)benzoate..]. 19. The composition of claim 11, wherein said compound is ethanolammonium
2-nitro-5-(2',4',6'-trichlorophenoxy)benzoate. 20. The composition of claim 11, wherein said compound is sodium 2-nitro-5-(2',4',6'-trichlorophenoxy)benzoate.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/075,369 USRE32316E (en) | 1969-04-25 | 1979-09-14 | Substituted phenoxybenzoic acids and derivatives thereof |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US81941269A | 1969-04-25 | 1969-04-25 | |
| US06/075,369 USRE32316E (en) | 1969-04-25 | 1979-09-14 | Substituted phenoxybenzoic acids and derivatives thereof |
Related Parent Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US19447971A Continuation-In-Part | 1969-04-25 | 1971-11-01 | |
| US396630A Reissue US3929455A (en) | 1971-11-01 | 1973-09-12 | Herbicidal halophenoxy benzoic acid salts |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| USRE32316E true USRE32316E (en) | 1986-12-30 |
Family
ID=26756757
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US06/075,369 Expired - Lifetime USRE32316E (en) | 1969-04-25 | 1979-09-14 | Substituted phenoxybenzoic acids and derivatives thereof |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | USRE32316E (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4911754A (en) | 1987-07-16 | 1990-03-27 | American Cyanamid Company | Herbicidally active aryloxy saturated 5-membered benzo fused hetero-cyclic compounds |
Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3169849A (en) * | 1958-07-09 | 1965-02-16 | Upjohn Co | Method for controlling growth of undesired vegetation |
| US3423470A (en) * | 1965-12-09 | 1969-01-21 | Ciba Ltd | Pesticidal preparations and compounds |
| US3475427A (en) * | 1966-02-03 | 1969-10-28 | Smithkline Corp | Phenoxazines |
| DE2019821A1 (en) * | 1969-04-25 | 1970-11-12 | Mobil Oil Corp | Halophenoxybenzoic acids as herbicides and processes for their use |
| US3776961A (en) * | 1971-12-23 | 1973-12-04 | Oil Corp | 3-substituted 4-nitrophenyl halophenyl ethers |
| US3798276A (en) * | 1972-03-14 | 1974-03-19 | H Bayer | Herbicidal 4-trifluoromethyl-4'-nitrodiphenyl ethers |
-
1979
- 1979-09-14 US US06/075,369 patent/USRE32316E/en not_active Expired - Lifetime
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3169849A (en) * | 1958-07-09 | 1965-02-16 | Upjohn Co | Method for controlling growth of undesired vegetation |
| US3423470A (en) * | 1965-12-09 | 1969-01-21 | Ciba Ltd | Pesticidal preparations and compounds |
| US3475427A (en) * | 1966-02-03 | 1969-10-28 | Smithkline Corp | Phenoxazines |
| DE2019821A1 (en) * | 1969-04-25 | 1970-11-12 | Mobil Oil Corp | Halophenoxybenzoic acids as herbicides and processes for their use |
| US3776961A (en) * | 1971-12-23 | 1973-12-04 | Oil Corp | 3-substituted 4-nitrophenyl halophenyl ethers |
| US3798276A (en) * | 1972-03-14 | 1974-03-19 | H Bayer | Herbicidal 4-trifluoromethyl-4'-nitrodiphenyl ethers |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4911754A (en) | 1987-07-16 | 1990-03-27 | American Cyanamid Company | Herbicidally active aryloxy saturated 5-membered benzo fused hetero-cyclic compounds |
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