US3321292A - 4-methylsulfonyl-2, 6-dinitro-n, n-substituted anilines as herbicides - Google Patents
4-methylsulfonyl-2, 6-dinitro-n, n-substituted anilines as herbicides Download PDFInfo
- Publication number
- US3321292A US3321292A US494268A US49426865A US3321292A US 3321292 A US3321292 A US 3321292A US 494268 A US494268 A US 494268A US 49426865 A US49426865 A US 49426865A US 3321292 A US3321292 A US 3321292A
- Authority
- US
- United States
- Prior art keywords
- methylsulfonyl
- dinitro
- herbicides
- soil
- ethyl
- 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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- 239000004009 herbicide Substances 0.000 title description 19
- 150000001448 anilines Chemical class 0.000 title description 3
- 230000002363 herbicidal effect Effects 0.000 claims description 25
- 239000000203 mixture Substances 0.000 claims description 24
- 150000001875 compounds Chemical class 0.000 claims description 9
- 241000196324 Embryophyta Species 0.000 description 23
- 239000002689 soil Substances 0.000 description 17
- 239000013543 active substance Substances 0.000 description 16
- 125000004432 carbon atom Chemical group C* 0.000 description 16
- -1 alkylene radical Chemical class 0.000 description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- VSHTWPWTCXQLQN-UHFFFAOYSA-N n-butylaniline Chemical compound CCCCNC1=CC=CC=C1 VSHTWPWTCXQLQN-UHFFFAOYSA-N 0.000 description 11
- 239000003921 oil Substances 0.000 description 11
- 235000019198 oils Nutrition 0.000 description 11
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 10
- VBEGHXKAFSLLGE-UHFFFAOYSA-N n-phenylnitramide Chemical class [O-][N+](=O)NC1=CC=CC=C1 VBEGHXKAFSLLGE-UHFFFAOYSA-N 0.000 description 10
- CDZOGLJOFWFVOZ-UHFFFAOYSA-N n-propylaniline Chemical compound CCCNC1=CC=CC=C1 CDZOGLJOFWFVOZ-UHFFFAOYSA-N 0.000 description 10
- 239000002904 solvent Substances 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- OJGMBLNIHDZDGS-UHFFFAOYSA-N N-Ethylaniline Chemical compound CCNC1=CC=CC=C1 OJGMBLNIHDZDGS-UHFFFAOYSA-N 0.000 description 8
- 125000003342 alkenyl group Chemical group 0.000 description 8
- 125000000217 alkyl group Chemical group 0.000 description 8
- 238000000034 method Methods 0.000 description 7
- 239000007921 spray Substances 0.000 description 7
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 6
- 230000008635 plant growth Effects 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 5
- 244000055702 Amaranthus viridis Species 0.000 description 5
- UMKANAFDOQQUKE-UHFFFAOYSA-N Nitralin Chemical compound CCCN(CCC)C1=C([N+]([O-])=O)C=C(S(C)(=O)=O)C=C1[N+]([O-])=O UMKANAFDOQQUKE-UHFFFAOYSA-N 0.000 description 5
- 239000004480 active ingredient Substances 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 239000000839 emulsion Substances 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 4
- 239000006185 dispersion Substances 0.000 description 4
- LQFLWKPCQITJIH-UHFFFAOYSA-N n-allyl-aniline Chemical compound C=CCNC1=CC=CC=C1 LQFLWKPCQITJIH-UHFFFAOYSA-N 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- 235000013479 Amaranthus retroflexus Nutrition 0.000 description 3
- 235000004135 Amaranthus viridis Nutrition 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 239000004215 Carbon black (E152) Substances 0.000 description 3
- 235000009344 Chenopodium album Nutrition 0.000 description 3
- 235000005484 Chenopodium berlandieri Nutrition 0.000 description 3
- 235000009332 Chenopodium rubrum Nutrition 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 3
- 244000236458 Panicum colonum Species 0.000 description 3
- 235000015225 Panicum colonum Nutrition 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
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- 239000013078 crystal Substances 0.000 description 3
- 239000003995 emulsifying agent Substances 0.000 description 3
- 229930195733 hydrocarbon Natural products 0.000 description 3
- 150000002430 hydrocarbons Chemical class 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 239000000080 wetting agent Substances 0.000 description 3
- BFIMMTCNYPIMRN-UHFFFAOYSA-N 1,2,3,5-tetramethylbenzene Chemical compound CC1=CC(C)=C(C)C(C)=C1 BFIMMTCNYPIMRN-UHFFFAOYSA-N 0.000 description 2
- 235000001602 Digitaria X umfolozi Nutrition 0.000 description 2
- 235000017898 Digitaria ciliaris Nutrition 0.000 description 2
- 235000005476 Digitaria cruciata Nutrition 0.000 description 2
- 235000006830 Digitaria didactyla Nutrition 0.000 description 2
- 235000005804 Digitaria eriantha ssp. eriantha Nutrition 0.000 description 2
- 235000010823 Digitaria sanguinalis Nutrition 0.000 description 2
- 244000025670 Eleusine indica Species 0.000 description 2
- 235000014716 Eleusine indica Nutrition 0.000 description 2
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
- 241000209082 Lolium Species 0.000 description 2
- 239000011149 active material Substances 0.000 description 2
- 125000002947 alkylene group Chemical group 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000007859 condensation product Substances 0.000 description 2
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 2
- 239000000428 dust Substances 0.000 description 2
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- 230000035784 germination Effects 0.000 description 2
- 230000012010 growth Effects 0.000 description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 150000004668 long chain fatty acids Chemical class 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 125000005394 methallyl group Chemical group 0.000 description 2
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- XFUDCMVAWAFVPF-UHFFFAOYSA-N n,n-diethyl-4-methylsulfonyl-2,6-dinitroaniline Chemical compound CCN(CC)C1=C([N+]([O-])=O)C=C(S(C)(=O)=O)C=C1[N+]([O-])=O XFUDCMVAWAFVPF-UHFFFAOYSA-N 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000008247 solid mixture Substances 0.000 description 2
- HHVIBTZHLRERCL-UHFFFAOYSA-N sulfonyldimethane Chemical compound CS(C)(=O)=O HHVIBTZHLRERCL-UHFFFAOYSA-N 0.000 description 2
- JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical class OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 description 1
- LDVVMCZRFWMZSG-OLQVQODUSA-N (3ar,7as)-2-(trichloromethylsulfanyl)-3a,4,7,7a-tetrahydroisoindole-1,3-dione Chemical compound C1C=CC[C@H]2C(=O)N(SC(Cl)(Cl)Cl)C(=O)[C@H]21 LDVVMCZRFWMZSG-OLQVQODUSA-N 0.000 description 1
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- IAKOZHOLGAGEJT-UHFFFAOYSA-N 1,1,1-trichloro-2,2-bis(p-methoxyphenyl)-Ethane Chemical compound C1=CC(OC)=CC=C1C(C(Cl)(Cl)Cl)C1=CC=C(OC)C=C1 IAKOZHOLGAGEJT-UHFFFAOYSA-N 0.000 description 1
- PRPINYUDVPFIRX-UHFFFAOYSA-N 1-naphthaleneacetic acid Chemical compound C1=CC=C2C(CC(=O)O)=CC=CC2=C1 PRPINYUDVPFIRX-UHFFFAOYSA-N 0.000 description 1
- CGNBQYFXGQHUQP-UHFFFAOYSA-N 2,3-dinitroaniline Chemical class NC1=CC=CC([N+]([O-])=O)=C1[N+]([O-])=O CGNBQYFXGQHUQP-UHFFFAOYSA-N 0.000 description 1
- XOXDOVDWSOCMQD-UHFFFAOYSA-N 2-chloro-5-methylsulfonyl-1,3-dinitrobenzene Chemical compound CS(=O)(=O)C1=CC([N+]([O-])=O)=C(Cl)C([N+]([O-])=O)=C1 XOXDOVDWSOCMQD-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- GZNCKEGJECDSPF-UHFFFAOYSA-N 4-methylsulfonyl-2,6-dinitroaniline Chemical class CS(=O)(=O)C1=CC([N+]([O-])=O)=C(N)C([N+]([O-])=O)=C1 GZNCKEGJECDSPF-UHFFFAOYSA-N 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- 241000219318 Amaranthus Species 0.000 description 1
- 241001148727 Bromus tectorum Species 0.000 description 1
- 239000005745 Captan Substances 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 235000008733 Citrus aurantifolia Nutrition 0.000 description 1
- 239000005749 Copper compound Substances 0.000 description 1
- YVGGHNCTFXOJCH-UHFFFAOYSA-N DDT Chemical compound C1=CC(Cl)=CC=C1C(C(Cl)(Cl)Cl)C1=CC=C(Cl)C=C1 YVGGHNCTFXOJCH-UHFFFAOYSA-N 0.000 description 1
- KKUKTXOBAWVSHC-UHFFFAOYSA-N Dimethylphosphate Chemical compound COP(O)(=O)OC KKUKTXOBAWVSHC-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 244000211187 Lepidium sativum Species 0.000 description 1
- 235000007849 Lepidium sativum Nutrition 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 240000004460 Tanacetum coccineum Species 0.000 description 1
- 235000011941 Tilia x europaea Nutrition 0.000 description 1
- 229920004890 Triton X-100 Polymers 0.000 description 1
- 239000013504 Triton X-100 Substances 0.000 description 1
- ROVGZAWFACYCSP-MQBLHHJJSA-N [2-methyl-4-oxo-3-[(2z)-penta-2,4-dienyl]cyclopent-2-en-1-yl] (1r,3r)-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropane-1-carboxylate Chemical compound CC1(C)[C@H](C=C(C)C)[C@H]1C(=O)OC1C(C)=C(C\C=C/C=C)C(=O)C1 ROVGZAWFACYCSP-MQBLHHJJSA-N 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000002877 alkyl aryl group Chemical group 0.000 description 1
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- 125000004369 butenyl group Chemical group C(=CCC)* 0.000 description 1
- 229940117949 captan Drugs 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
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- OEBRKCOSUFCWJD-UHFFFAOYSA-N dichlorvos Chemical compound COP(=O)(OC)OC=C(Cl)Cl OEBRKCOSUFCWJD-UHFFFAOYSA-N 0.000 description 1
- DFBKLUNHFCTMDC-PICURKEMSA-N dieldrin Chemical compound C([C@H]1[C@H]2[C@@]3(Cl)C(Cl)=C([C@]([C@H]22)(Cl)C3(Cl)Cl)Cl)[C@H]2[C@@H]2[C@H]1O2 DFBKLUNHFCTMDC-PICURKEMSA-N 0.000 description 1
- 229950006824 dieldrin Drugs 0.000 description 1
- NGPMUTDCEIKKFM-UHFFFAOYSA-N dieldrin Natural products CC1=C(Cl)C2(Cl)C3C4CC(C5OC45)C3C1(Cl)C2(Cl)Cl NGPMUTDCEIKKFM-UHFFFAOYSA-N 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- FAXIJTUDSBIMHY-UHFFFAOYSA-N diethoxy-(2-ethylsulfanylethoxy)-sulfanylidene-$l^{5}-phosphane;1-diethoxyphosphorylsulfanyl-2-ethylsulfanylethane Chemical compound CCOP(=O)(OCC)SCCSCC.CCOP(=S)(OCC)OCCSCC FAXIJTUDSBIMHY-UHFFFAOYSA-N 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- WHDGWKAJBYRJJL-UHFFFAOYSA-K ferbam Chemical compound [Fe+3].CN(C)C([S-])=S.CN(C)C([S-])=S.CN(C)C([S-])=S WHDGWKAJBYRJJL-UHFFFAOYSA-K 0.000 description 1
- 239000003337 fertilizer Substances 0.000 description 1
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- 150000002334 glycols Chemical class 0.000 description 1
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- 239000008233 hard water Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000004571 lime Substances 0.000 description 1
- 239000010687 lubricating oil Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 125000006178 methyl benzyl group Chemical group 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 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
- DYUWTXWIYMHBQS-UHFFFAOYSA-N n-prop-2-enylprop-2-en-1-amine Chemical compound C=CCNCC=C DYUWTXWIYMHBQS-UHFFFAOYSA-N 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- BUYMVQAILCEWRR-UHFFFAOYSA-N naled Chemical compound COP(=O)(OC)OC(Br)C(Cl)(Cl)Br BUYMVQAILCEWRR-UHFFFAOYSA-N 0.000 description 1
- 230000001069 nematicidal effect Effects 0.000 description 1
- 239000005645 nematicide Substances 0.000 description 1
- 231100001184 nonphytotoxic Toxicity 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 238000003359 percent control normalization Methods 0.000 description 1
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- 238000005191 phase separation Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 229940015367 pyrethrum Drugs 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229940080817 rotenone Drugs 0.000 description 1
- JUVIOZPCNVVQFO-UHFFFAOYSA-N rotenone Natural products O1C2=C3CC(C(C)=C)OC3=CC=C2C(=O)C2C1COC1=C2C=C(OC)C(OC)=C1 JUVIOZPCNVVQFO-UHFFFAOYSA-N 0.000 description 1
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- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C317/00—Sulfones; Sulfoxides
- C07C317/26—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
- C07C317/32—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton with sulfone or sulfoxide groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C317/34—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton with sulfone or sulfoxide groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having sulfone or sulfoxide groups and amino groups bound to carbon atoms of six-membered aromatic rings being part of the same non-condensed ring or of a condensed ring system containing that ring
Definitions
- This invention relates to a method useful in destroying and/ or preventing growth of unwanted plants and to herbicidal compositions.
- this invention relates to the use and compositions containing novel 4-(methylsulfonyl)-2,6-dinitro-N,N-substituted anilines found to be very active herbicides.
- herbicidal compounds used according to the invention are represented by the generic formula:
- R and R" each is alkyl or alkenyl of at least two carbon atoms but together contain a total of no more than eight carbon atoms; R and R" together may form an alkylene radical of up to 8 carbon atoms.
- alkyl substituents as ethyl, isopropyl, n-propyl, n-butyl are suitable while suitable alkenyl groups include vinyl, allyl, methallyl or butenyl.
- the alkyl or alkenyl substituents may be straightor branched-chain.
- R and R may be the same or they may be difierent. Both may be alkyl or alkenyl or R may be alkyl while R" is alkenyl.
- herbicidal nitroanilines used according to the invention are:
- Example I Preparation of 4-(methylsulfo'nyl)-2,6- dinitro-N,N-dipropylaniline
- A Preparation of 4-chZora-3,5-ziinizrophenyl methylsz llfone.-6 parts of 4-chloro-3-nitrophenyl methylsultone was added portionwise to a mixture of 49 parts of turning H 50 (30%) and 16 parts of red fuming HNO (d. 1.60) at 30 C. The reaction was heated with stirring to 140 C. for 3 hours, then poured over ice. The separated solid was filtered, water-washed, and dried. The product was recrystallized from dimethyl formamide solution by adding alcohol to give 4.5 parts of pale yellow crystals, M.P. 201-203 C. Structure confirmed by elemental analysisviz. (percent by weight).
- Example II Preparazi0n of 4-methylsulf0nyl-2,6-dinitr0- N,N-diallylaniline 14 parts of 4-chloro- 3,S-dinitrophenyl methyl sulfone was suspended in 120 parts of methanol in a reaction flask equipped with a mechanical stirrer. 10 parts of diallyl amine was added to the mixture dropwise. The reaction mixture was heated to reflux for 1 /2 hours, cooled in an acetone-Dry Ice bath, and solid which formed was filtered. The solid was recrystallized from methanol to give 12 parts of yellow crystals, M.P. l08111 C. (71% yield). Structure confirmed by elemental analysis-viz. (percent by weight).
- Example III TABLE I.PRE-EMERGENCE SOIL HERBICIDE TESTS 10 1bs./A Watergrass 10 lbs/A Test Compound Cress 4- (methylsulfonyl)-2,6-dinitro-N,N-diethyla ne 4- (methylsulfonyl)-2 nitr-N,N-dipropylaniline 4- (methylsulfonyl)-2,6-dinitr0-N ,N-dibu tylaniline 4-(methylsulfonyl)-2,6'dinitro-N-propy1, N
- butylaniline 4- (mcthylsult'onyl) -2,6-dinitro-N- butylaniline 4- (methylsulfonyl) -2,6-dinitr propylam'line 4-(methylsulfonyl)-2,6-diuitro-N,N-dial1ylaniline ethylaniline -(methylsulfonyl 2,6
- Example V.-Field tests The pre-emergent and post-emergent activity of 4- (methylsulfonyl)-2,6-dinitro-N,N-dipropylaniline has been evaluated in field tests. When a logarithmic series of dosages of this compound was sprayed onto bare soil, it was found that control of ryegrass was obtained at 0.8 pound per acre while less than 0.2 pound per acre controlled crabgrass. This nitroaniline is therefore a highly effective pre-emergent herbicide.
- nitroaniline herbicides of this invention are not very volatile, and tend to remain in that part of the soil into which they are introduced; some may be moved through the soil by water. Consequently, by appropriate selection of the part of the soil into which they are introduced, relative to the seeds of wanted plants and those of unwanted plants, and taking into account the effect of water, these herbicides can be used to prevent all plant growth, even at relatively low dosages in some cases, or their selectivity can be improved to prevent growth of unwanted plants without harm to wanted plants.
- the nitroanilines are soluble in the common organic horticultural solvents.
- the herbicidal nitroanilines can be formulated as a solution or suspension in water, or a suitable nonphytotoxic organic solvent, as a dispersion or emulsion of the active agent in a non-solvent therefor, as an emulsion of a solution of the active agent in a suitable solvent emulsified with a second, inhomogeneous liquid, or as a solid comprising the active agent or agents sorbed on a sorptive solid carrier.
- suitable materials for the purpose include any of the spray oils marketed commercially for this purpose.
- the highly aromatic hydrocarbons are preferred.
- highly refined aromatic hydrocarbons such as benzene, toluene, xylene, ethylbenzene, cumene or isodurene
- the carrier may be a less highly refined relatively aromatic hydrocarbon mixture, such as a coal tar fraction, a straight-run petroleum distillate, a thermally or catalytically cracked hydrocarbon oil, platformate, or the like.
- Suitable solvents may also comprise a relatively aliphatic hydrocarbon material, or mixtures of aromatic and aliphatic hydrocarbons.
- Suitable aliphatic hydrocarbon ma terials include refined gas oil, light lubricating oil fractions, refined derosene, mineral seal oil and the like.
- Spray oils boiling in the range of from 275 F. to 575 F. are suitable, as are spray oils boiling in the range of from 575 to 1000 F. and having an unsulfonatable residue of at least 75 Mixtures of such spray oils also may be used.
- the solvent usually will be of mineral origin, animal or vegetable oils as well as synthetic solvents also may be employed in or as the carrier.
- oxygenated solvents such as alcohols, e.g., methanol, ethanol, isopropyl alcohol, n-butyl alcohol and amyl alcohol, ketones, e.g., acetone, methyl ethyl ketone, methyl isobutyl ketone, etc.
- glycols and glycol ethers and chlorinated solvents may be employed in or as the carrier.
- Solutions of the active agents may be applied as such to the plants or to the soil that is to be treated, or they may be suspended in water and the suspension or emulsion applied to the plants or soil.
- a relatively concentrated solution of the active agent in a water-immiscible solvent may be prepared, with added emulsifying, dispersing or other surface-active agents, and the concentrate diluted in the spray tank with water to form a uniform fine emulsion which can be applied by conventional spray devices.
- Emulsions or dispersions of the active agents as such in water may also be prepared and applied.
- Suitable emulsifiable concentrates adapted for dispersion in water to provide a sprayable composition, ordinarily will contain between about by Weight and about 50% by weight of active agent dissolved in a hydrocarbon or other suitable water-immiscible solvent. Minor amounts, for example, about 0.5% by weight to about by weight, of emulsifying agents may be included to promote dispersion of the concentrate in Water.
- Suitable emulsifying agents include, among others, alkaryl sulfonates, sulfates of long-chain fatty acids, alkylaryl polyoxyethylene glycol ethers, sulfonated white oils, sorbitan esters of long-chain fatty acids, alkylamide sulfonates and the like.
- non-ionic agents are preferred since the concentrates in which they are present have increased stability and do not suffer phase separation when diluted with hard water.
- Suitable non-ionic agents which may be used are available commercially as, for example, Triton X-100 and Lissapol Nbelieved to be condensation products of alkylphenols with ethylene oxide-and Tweens-believed to be condensation products of ethylene oxide and higher fatty acids esters, for example, oleic acid ester of anhydrosorbitols.
- Liquid compositions of these herbicidal nitroanilines suitable for application to plants or to their environment contain the active agent or agents in concentrations generally within the range of from about 0.01% by Weight to about 50% by weight.
- the invention includes novel solid compositions of matter wherein the active agent or agents are absorbed or absorbed in or on a sorptive carrier, such as finely divided clay, talc, gypsum, lime, wood flour, fullers earth, kieselguhr, or the like.
- a sorptive carrier such as finely divided clay, talc, gypsum, lime, wood flour, fullers earth, kieselguhr, or the like.
- the solid composition, or dust may contain from as little as 1% by weight of active material to 75% by weight of active material, or even more. It may be prepared as a dust, or as granules designed to be broadcast or to be worked into the soil.
- Compositions formulated as wettable powders are particularly suitable. Wettable powders can be prepared suitable for suspension in water with or without the aid of conventional dispersing or deflocculating agents and with or without such adjuvants as oils, stickers, wetting agents, etc.
- the rate of application of the active agent may be varied from about 0.1 to 30 or more pounds per acre. It will be appreciated that the rate of application is subject to variation according to the particular active agent used, the particular species of plants involved, and the local conditions, for example, temperature, humidity, moisture content of the soil, nature of the soil, and the like. Efiective resolution of these factors is well within the skill of those well versed in the herbicide art.
- the herbicidal compositions may contain one or more of the herbicidal nitroanilines set out hereinbefore as the sole active agent, or they may contain in addition thereto other biologically active substances.
- insecticides e.g., DDT, endrin, dieldrin, aldrin, chlordane, demeton, methoxychlor, DDVP, naled, methylbenzyl B-hydroxycrotonate dimethyl phosphate, rotenone and pyrethrum
- fungicides such as copper compounds, ferbam, captan, and the like, may be incorporated in the compositions.
- the herbicidal compositions may contain fertilizers, trace metals, or the like and when applied directly to the soil may additionally contain nematocides, soil conditioners other plant regulators, such as naphthalene acetic acid, 2.4-dichlorophenoxyacetic acid and the like, and/or herbicides of difierent properties.
- a herbicidal composition comprising from about 1 percent to about 75 percent by weight of the total composition of a compound of the formula:
- R and R each is a member of the group consisting of alkenyl of at least two carbon atoms and alkyl of at least two carbon atoms, R and R" together containing a total of no more than eight carbon atoms, and with the proviso that R and R" together can represent unsubstituted alkylene of six to seven carbon atoms, and an inert horticultural diluent therefor.
- R and R each is a member of the group consisting of alkenyl of at least two carbon atoms and alkyl of at least two carbon atoms, R and R together containing a total of from five to seven carbon atoms.
- a herbicidal composition according to claim 1 wherein the active ingredient is 4-(methylsulfonyl)-2,6- dinitro-N,N-dipropylaniline.
- a herbicidal composition wherein the active ingredient is dinitro-N,N-diallylaniline.
- a herbicidal composition wherein the active ingredient is dinitro-N-propyl, N-butylaniline.
- a herbicidal composition wherein the active ingredient is dinitro-N-ethyl, N-butylaniline.
- a herbicidal composition wherein the active ingredient is dinitro-N-ethyl, N-propylaniline.
- R and R" each is a member of the group consisting of alkenyl of at least two carbon atoms and alkyl of at least two carbon atoms, R and R" containing a total of no more than eight carbon atoms, and with 7 8 the proviso that R and R" together can represent 13.
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Description
United States Patent 3,321,292 4-METHYLSULFONYL-2,6-D1NITRO-N,N-SUBSTI- TUTED ANILINES AS EERBICIDES Samuel B. Soloway, Sittingboume, England, and Kenneth D. Zwahien, Modesto, Califi, assignors to Shell Oil Company, New York, N.Y., a corporation of Delawere No Drawing. Filed Oct. 8, 1965, Ser. No. 494,268 13 Claims. (Cl. 712.3)
This invention is a continuationin-part of Serial No. 411,120, filed NOV. 13, 1964 now US. Patent No. 3,227,734.
This invention relates to a method useful in destroying and/ or preventing growth of unwanted plants and to herbicidal compositions. In particular, this invention relates to the use and compositions containing novel 4-(methylsulfonyl)-2,6-dinitro-N,N-substituted anilines found to be very active herbicides.
The herbicidal compounds used according to the invention are represented by the generic formula:
O l u wherein R and R" each is alkyl or alkenyl of at least two carbon atoms but together contain a total of no more than eight carbon atoms; R and R" together may form an alkylene radical of up to 8 carbon atoms.
Such alkyl substituents as ethyl, isopropyl, n-propyl, n-butyl are suitable while suitable alkenyl groups include vinyl, allyl, methallyl or butenyl. The alkyl or alkenyl substituents may be straightor branched-chain.
R and R may be the same or they may be difierent. Both may be alkyl or alkenyl or R may be alkyl while R" is alkenyl.
Exemplary of such herbicidal nitroanilines used according to the invention are:
4-(methylsulfonyl)-2,6-dinitro-N,N-diethylaniline 4- (methylsulfonyl) -2,6-dinitro-N,N dipropylaniline 4-(methylsulfonyl)-2,6-dinitro-N,N-dibutylaniline 4-(methy1sulfonyl)-2,6-dinitro- -ethyl, N-propylaniline 4-(methylsulfonyl)-2,6-dinitro-N-ethyl, N-butylaniline 4-(rnethylsulfonyl)-2,6-dinitro-N-propyl, N-butylaniline 4-(methylsulfonyl)-2,6-dinitro-N-viny1, N-ethylaniline 4-(methylsulfonyl)-2,6-dinitro-N-viny1, N-propylaniline 4- (methylsulfonyl)-2,6-dinitro-N,N-diallylauiline 4-(methylsulfonyl -2,6-dinitro-N-allyl, N-ethylaniline 4-(methylsulfonyl)-2,6-dinitro-N-allyl, N-propylaniline 4-(methylsulfonyl)-2,6-dinitro-N-allyl, N-butylaniline 4- (methylsulfonyl) -2, 6-dinitro-N,N-di Z-methallyl) aniline 4- methylsnlfonyl) -2,6-dinitro-N- (Z-methally) N-ethylaniline 4-( methylsulfonyl -2,6-dinitro-N- (2-meth allyl) N-propylaniline 4-(methylsulfonyl)-2,6-dinitro-N-butenyl, N-allylaniline 4-(methylsulfonyl)-2,6-dinitro-N-butenyl, N-propylaniline l- [4- (methylsulfonyl) -2,6-dinitrophenyl] hexahydrolH-azepine 1- [4- (methylsulfonyl) -2,6-dinitrophenyl] octahydro lH-azocine Preferred because of their especially eflective herbi cidal properties and their ability to control weeds at relatively low dosages are those nitroanilines wherein R and R" are independently alkyl or alkenyl of at least two carbon atoms and R and R" together contain from t0 7 carbon atoms. It has been found that when R or R", for example, is represented by hydrogen or methyl, the resulting 4-(methylsulfonyl)-2,6-dinitroanilines are rela- 3,321,292 Patented May 23, 1967 No. of C atoms, Lbs. per acre for R'+R" control Tests on other plant species have confirmed this finding. The nitroanilines of this preferred class are effective herbicides against a wide range of economically important weeds.
Examples of such preferred herbicides are:
4-(methylsulfonyl)-2,6-dinitro-N-ethyl, N-propylaniline 4-(methylsulfonyl)-2,6-dinitro-N-ethyl, N-butylaniline 4-(methylsulfonyl -2,6-dinitro-N,N-dipropylaniline 4-(methylsulfonyl)-2,6-dinitro-N-propyl, N-butylaniline 4-(methylsulfonyl)-2,6-dinitro-N-ethyl, N-allylaniline 4-(methylsulfonyl)-2,6-dinitro-N-propyl, N-allylaniline 4- (methylsulfonyl -2,6-dinitro-N,N-diallylaniline The following examples are presented to show how typical compounds used according to the invention can be prepared and to illustrate the effectiveness of typical members as herbicides.
In the following examples, the parts given are by weight.
Example I .Preparation of 4-(methylsulfo'nyl)-2,6- dinitro-N,N-dipropylaniline A. Preparation of 4-chZora-3,5-ziinizrophenyl methylsz llfone.-6 parts of 4-chloro-3-nitrophenyl methylsultone was added portionwise to a mixture of 49 parts of turning H 50 (30%) and 16 parts of red fuming HNO (d. 1.60) at 30 C. The reaction was heated with stirring to 140 C. for 3 hours, then poured over ice. The separated solid was filtered, water-washed, and dried. The product was recrystallized from dimethyl formamide solution by adding alcohol to give 4.5 parts of pale yellow crystals, M.P. 201-203 C. Structure confirmed by elemental analysisviz. (percent by weight).
Calculated for N SO ClC H Cl, 13.7; N, 10.0. Found: Cl, 12.9;N, 10.0.
B. Preparation of 4-(methylsulfonyl)-2,6-dinitr0-N,N- dipr0pylaniline.l5 parts of 4-chloro-3,S-dinitrophenyl methylsulfone was suspended in 120 parts of methanol and 15 parts of dipropylamine were added. The reaction mixture was heated for two hours, chilled, and the separated solid filtered. The produnct was Washed and recrystallized to give 18 parts of golden crystals, M.P. 151 C. (97% yield). Structure confirmed by elemental analysis-viz. (percent by weight).
Calculated for N SO C H N, 12.2; S, 9.3. Found: N, 12.0; S, 9.3.
Example II.-Preparazi0n of 4-methylsulf0nyl-2,6-dinitr0- N,N-diallylaniline 14 parts of 4-chloro- 3,S-dinitrophenyl methyl sulfone was suspended in 120 parts of methanol in a reaction flask equipped with a mechanical stirrer. 10 parts of diallyl amine was added to the mixture dropwise. The reaction mixture was heated to reflux for 1 /2 hours, cooled in an acetone-Dry Ice bath, and solid which formed was filtered. The solid was recrystallized from methanol to give 12 parts of yellow crystals, M.P. l08111 C. (71% yield). Structure confirmed by elemental analysis-viz. (percent by weight).
Calculated for =N SO C H N, 12.3; S, 9.4. Found: N, 11.0; S, 9.1.
In a similar manner other dinitroanilines according to the invention were prepared by reacting the appropriate amine with 4-chloro-3,5-dinitrophenyl met-hylsulfone in a manner similar to that of Example I;
Example III TABLE I.PRE-EMERGENCE SOIL HERBICIDE TESTS 10 1bs./A Watergrass 10 lbs/A Test Compound Cress 4- (methylsulfonyl)-2,6-dinitro-N,N-diethyla ne 4- (methylsulfonyl)-2 nitr-N,N-dipropylaniline 4- (methylsulfonyl)-2,6-dinitr0-N ,N-dibu tylaniline 4-(methylsulfonyl)-2,6'dinitro-N-propy1, N
butylaniline 4- (mcthylsult'onyl) -2,6-dinitro-N- butylaniline 4- (methylsulfonyl) -2,6-dinitr propylam'line 4-(methylsulfonyl)-2,6-diuitro-N,N-dial1ylaniline ethylaniline -(methylsulfonyl 2,6
methallyl) aniline. 1-[4-(methylsulfonyl)-2,6-dinitr0pl1enyl]hexahydro-lH-azepine Ht (methylsulfonyl) -2,6-dim'trophenyl]oct0- hydro-lH-azocine moowocoooooow Example IV The post-emergence herbicide activity of the compounds used according to the invention was evaluated by spraying dilute suspensions of the compounds in a 1:1 mixture of acetone and water with 0.5% wetting agent on crabgrass (Digitarz'a sanguinalis) and pigweed plants (Amaranthus sp.) grown under controlled conditions. After the plants were held for 1 0 to 11 days, they were rated for treatment effect on a 0 (no effect) to 9 (total plant kill) scale. The results are set forth in Table II.
TABLE II.POST-EMERGENCE SPRAY HERBICIDE TESTS Weed control rating Test Compound 10 lbs/A Orabgrass 10 lbs/A Pigweed 4-(methylsulfonyl)-2,6dinitro-N,N-diethylaniline 4-(methylsulf'onyl) -2,6-dinitro-N,N-dipropylaniline 4-(methylsulionyl 2,6
aniline 4(methylsulfonyl)-2,6-dinitro-N-pr0pyl, N-
butylaniline 4-(methylsulfonyl)-2,6dinitro-N-ethyl, N
propylaniline 4 (methylsulfonyl) 2 fi-dinitro-N N-diallylaniline 4(methylsulfonyl)-2,6 initro-N-ethyl, N-
allylaniline 4-(methylsulfonyD-2,6-dinitro-N-propy1, N-
allylaniline Example V.-Field tests The pre-emergent and post-emergent activity of 4- (methylsulfonyl)-2,6-dinitro-N,N-dipropylaniline has been evaluated in field tests. When a logarithmic series of dosages of this compound was sprayed onto bare soil, it was found that control of ryegrass was obtained at 0.8 pound per acre while less than 0.2 pound per acre controlled crabgrass. This nitroaniline is therefore a highly effective pre-emergent herbicide.
:In further pre-emergence tests watergrass and pigweed plants were controlled with 4-(methylsulfonyl)-2,6-dinitro-N,N-dipropylaniline in the field at a series of logarithmic dosages and it was found that 95% control of watergrass was obtained at the dosage of 0.3 pound per acre while 1.6 pounds per acre controlled 95% of the pigweed. 4-(methylsulfonyl)-2,6-dinitro N,N-dipropylaniline is also a very promising post-emergent herbicide.
In a similar pre-emergent tests, 4(methylsulfonyl)-2,6- dinitro-N,N-diallylaniline controlled 95% of ryegrass at 2.7 pounds per acre, cheatgrass at 6.1 pounds per acre, dock and pigweed at less than 1 pound per acre.
Also active as pre-emergent herbicides in advanced tests were 4-(methylsulfonyl)-2,6-dinitro-N-propyl, N- butylaniline; 4-(methylsulfonyl)-2,6-dinitro-N-ethyl, N- butylaniline; 4-(methylsulfonyl)-2,6-dinitro-N-ethyl, N- propylaniline and 4-(methylsulfonyl)-2,6-dinitro, N- propyl, N-allylaniline.
One advantage of the nitroaniline herbicides of this invention is that they are not very volatile, and tend to remain in that part of the soil into which they are introduced; some may be moved through the soil by water. Consequently, by appropriate selection of the part of the soil into which they are introduced, relative to the seeds of wanted plants and those of unwanted plants, and taking into account the effect of water, these herbicides can be used to prevent all plant growth, even at relatively low dosages in some cases, or their selectivity can be improved to prevent growth of unwanted plants without harm to wanted plants. For example, as is well known, only those weed seeds which are present within about one-quarter inch of the surface of the soil will germinate, whereas the seeds of cereal, and other, crops, for example, ordinarily are sown about one-half to three-quarters of an inch below the surface of the soil, and germinate Well under those conditions. By introducing the herbicide only into the top one-quarter inch of the soil, and avoiding excessive watering, germination of the weed seeds can be prevented, while germination of the crop weeds will not be effected. Thus, even those herbicides of this invention that are not very selective in their action can be used to selectively remove the weeds from cereal grains or other crops. Of course, if complete kill of all plants in a given portion of soil is desired, it is necessary only to introduce one or more of the nitroanilines herbicides throughout that portion of soil.
The nitroanilines are soluble in the common organic horticultural solvents. Thus, according to the intended method of application, the character of the plants involved, and the concentration of herbicide to be used, the herbicidal nitroanilines can be formulated as a solution or suspension in water, or a suitable nonphytotoxic organic solvent, as a dispersion or emulsion of the active agent in a non-solvent therefor, as an emulsion of a solution of the active agent in a suitable solvent emulsified with a second, inhomogeneous liquid, or as a solid comprising the active agent or agents sorbed on a sorptive solid carrier.
When a light hydrocarbon oil is to be used as carrier, suitable materials for the purpose include any of the spray oils marketed commercially for this purpose. The highly aromatic hydrocarbons are preferred. Thus, highly refined aromatic hydrocarbons, such as benzene, toluene, xylene, ethylbenzene, cumene or isodurene, may be used, or the carrier may be a less highly refined relatively aromatic hydrocarbon mixture, such as a coal tar fraction, a straight-run petroleum distillate, a thermally or catalytically cracked hydrocarbon oil, platformate, or the like. Suitable solvents may also comprise a relatively aliphatic hydrocarbon material, or mixtures of aromatic and aliphatic hydrocarbons. Suitable aliphatic hydrocarbon ma terials include refined gas oil, light lubricating oil fractions, refined derosene, mineral seal oil and the like. Spray oils boiling in the range of from 275 F. to 575 F. are suitable, as are spray oils boiling in the range of from 575 to 1000 F. and having an unsulfonatable residue of at least 75 Mixtures of such spray oils also may be used.
Although the solvent usually will be of mineral origin, animal or vegetable oils as well as synthetic solvents also may be employed in or as the carrier. In appropriate cases oxygenated solvents, such as alcohols, e.g., methanol, ethanol, isopropyl alcohol, n-butyl alcohol and amyl alcohol, ketones, e.g., acetone, methyl ethyl ketone, methyl isobutyl ketone, etc., glycols and glycol ethers and chlorinated solvents may be employed in or as the carrier.
Solutions of the active agents may be applied as such to the plants or to the soil that is to be treated, or they may be suspended in water and the suspension or emulsion applied to the plants or soil. Thus, a relatively concentrated solution of the active agent in a water-immiscible solvent may be prepared, with added emulsifying, dispersing or other surface-active agents, and the concentrate diluted in the spray tank with water to form a uniform fine emulsion which can be applied by conventional spray devices. Emulsions or dispersions of the active agents as such in water may also be prepared and applied.
Suitable emulsifiable concentrates, adapted for dispersion in water to provide a sprayable composition, ordinarily will contain between about by Weight and about 50% by weight of active agent dissolved in a hydrocarbon or other suitable water-immiscible solvent. Minor amounts, for example, about 0.5% by weight to about by weight, of emulsifying agents may be included to promote dispersion of the concentrate in Water. Suitable emulsifying agents include, among others, alkaryl sulfonates, sulfates of long-chain fatty acids, alkylaryl polyoxyethylene glycol ethers, sulfonated white oils, sorbitan esters of long-chain fatty acids, alkylamide sulfonates and the like. Although both anionand cation-active wetting and emulsifying agents may be used for this purpose, the non-ionic agents are preferred since the concentrates in which they are present have increased stability and do not suffer phase separation when diluted with hard water. Suitable non-ionic agents which may be used are available commercially as, for example, Triton X-100 and Lissapol Nbelieved to be condensation products of alkylphenols with ethylene oxide-and Tweens-believed to be condensation products of ethylene oxide and higher fatty acids esters, for example, oleic acid ester of anhydrosorbitols.
Liquid compositions of these herbicidal nitroanilines suitable for application to plants or to their environment contain the active agent or agents in concentrations generally within the range of from about 0.01% by Weight to about 50% by weight.
The invention includes novel solid compositions of matter wherein the active agent or agents are absorbed or absorbed in or on a sorptive carrier, such as finely divided clay, talc, gypsum, lime, wood flour, fullers earth, kieselguhr, or the like. The solid composition, or dust, may contain from as little as 1% by weight of active material to 75% by weight of active material, or even more. It may be prepared as a dust, or as granules designed to be broadcast or to be worked into the soil. Compositions formulated as wettable powders are particularly suitable. Wettable powders can be prepared suitable for suspension in water with or without the aid of conventional dispersing or deflocculating agents and with or without such adjuvants as oils, stickers, wetting agents, etc.
For field application, the rate of application of the active agent may be varied from about 0.1 to 30 or more pounds per acre. It will be appreciated that the rate of application is subject to variation according to the particular active agent used, the particular species of plants involved, and the local conditions, for example, temperature, humidity, moisture content of the soil, nature of the soil, and the like. Efiective resolution of these factors is well within the skill of those well versed in the herbicide art.
The herbicidal compositions may contain one or more of the herbicidal nitroanilines set out hereinbefore as the sole active agent, or they may contain in addition thereto other biologically active substances. Thus, insecticides, e.g., DDT, endrin, dieldrin, aldrin, chlordane, demeton, methoxychlor, DDVP, naled, methylbenzyl B-hydroxycrotonate dimethyl phosphate, rotenone and pyrethrum, and fungicides, such as copper compounds, ferbam, captan, and the like, may be incorporated in the compositions. Further, if desired, the herbicidal compositions may contain fertilizers, trace metals, or the like and when applied directly to the soil may additionally contain nematocides, soil conditioners other plant regulators, such as naphthalene acetic acid, 2.4-dichlorophenoxyacetic acid and the like, and/or herbicides of difierent properties.
We claim as our invention:
1. A herbicidal composition comprising from about 1 percent to about 75 percent by weight of the total composition of a compound of the formula:
wherein R and R each is a member of the group consisting of alkenyl of at least two carbon atoms and alkyl of at least two carbon atoms, R and R" together containing a total of no more than eight carbon atoms, and with the proviso that R and R" together can represent unsubstituted alkylene of six to seven carbon atoms, and an inert horticultural diluent therefor.
2. A herbicidal composition according to claim 1 wherein R and R each is a member of the group consisting of alkenyl of at least two carbon atoms and alkyl of at least two carbon atoms, R and R together containing a total of from five to seven carbon atoms.
3. A herbicidal composition according to claim 1 wherein the active ingredient is 4-(methylsulfonyl)-2,6- dinitro-N,N-dipropylaniline.
4. A herbicidal composition wherein the active ingredient is dinitro-N,N-diallylaniline.
5. A herbicidal composition wherein the active ingredient is dinitro-N-propyl, N-butylaniline.
6. A herbicidal composition wherein the active ingredient is dinitro-N-ethyl, N-butylaniline.
7. A herbicidal composition wherein the active ingredient is dinitro-N-ethyl, N-propylaniline.
8. A method of controlling unwanted plant growth which comprises bringing into contact with said plants a herbicidally effective amount of a compound of the formula:
according to claim 1 4- (methylsulfonyl) -2,6-
according to claim 1 4- (methylsulfonyl) -2,6-
according to claim 1 4- (methylsulfonyl) -2,6-
according to claim 1 4- (methylsulfonyl -2,6-
wherein R and R" each is a member of the group consisting of alkenyl of at least two carbon atoms and alkyl of at least two carbon atoms, R and R" containing a total of no more than eight carbon atoms, and with 7 8 the proviso that R and R" together can represent 13. A method of controlling unwanted plant growth unsubstituted alkylene of from six to seven carbon according to claim 8 with 4-(methylsulfonyl)-2,6-dinitroatoms. N-ethyl, N-propylaniline. 9. A method of controlling unwanted plant growth according to claim 8 with 4-(methylsulfonyl)-2,6-dinitro- 5 References Cited y the Examiner ,i gg pyig g t H t d 1 t th UNITED STATES PATENTS me' 0 0 con r0 mg unwane pan grow according to claim 8 with 4-(methylsulfonyl)-2,6-dinitr0- 5P 71 2'3 meman 712.3 NNmanylamlme' 3 257 190 6/1966 So 6r 71- 2 3 11. A method of controlling unwanted plant growth 10 p according to claim 8 with 4-(methylsulfonyl)-2,6-dinitro- FOREIGN PATENTS N-pmPylN-butylaniline- 666,837 7/1963 Canada.
12. A method of controlling unwanted plant growth according to claim 8 with 4-(methylsulfonyl)-2,6-dinitro LEWIS GOTTS Pnmary Examme' N-ethyl, N-butylani'line. 15 JAMES O. THOMAS, ]R., Examiner.
Claims (1)
1. A HERBICIDAL COMPOSITION COMPRISING FROM ABOUT 1 PERCENT TO ABOUT 75 PERCENT BY WEIGHT OF THE TOTAL COMPOSITION OF A COMPOUND OF THE FORMULA
Priority Applications (12)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US411120A US3227734A (en) | 1964-11-13 | 1964-11-13 | Herbicidal 4-methylsulfonyl-2,6-dinitro-n,n-substituted anilines |
NL6510912A NL6510912A (en) | 1964-11-13 | 1965-08-20 | |
US494268A US3321292A (en) | 1964-11-13 | 1965-10-08 | 4-methylsulfonyl-2, 6-dinitro-n, n-substituted anilines as herbicides |
BE672199D BE672199A (en) | 1964-11-13 | 1965-11-10 | |
FR37949A FR1453170A (en) | 1964-11-13 | 1965-11-10 | 4- (methylsulfonyl) -2,6-dinitro-anilines substituted in n, n having herbicidal properties |
DK580965AA DK117037B (en) | 1964-11-13 | 1965-11-11 | 2,6-Dinitro-aniline derivatives for use in herbicides. |
CS6737A CS152423B2 (en) | 1964-11-13 | 1965-11-11 | |
CH1555765A CH484608A (en) | 1964-11-13 | 1965-11-11 | Weedkillers |
BR174766/65A BR6574766D0 (en) | 1964-11-13 | 1965-11-11 | HERBICIDIC COMPOSITIONS AND PROCESS FOR THE PREPARATION OF ANYLINES 4- (METHYLSULPHONYL) -2 6-DINITRO N N-REPLACED IN THEM APPLICABLE |
IL24613A IL24613A (en) | 1964-11-13 | 1965-11-11 | 4-(methylsulphonyl)-2,6-dinitro-n,n-substituted anilines,their preparation and use as herbicides |
GB47914/65A GB1056199A (en) | 1964-11-13 | 1965-11-11 | Herbicidal 4-(methylsulphonyl)-2,6-dinitro-n,n-substituted anilines |
DE1518333A DE1518333C3 (en) | 1964-11-13 | 1965-11-11 | N, N-substituted 4-methylsulfonyl-2,6-dinitroanilines, process for their preparation and their use |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US411120A US3227734A (en) | 1964-11-13 | 1964-11-13 | Herbicidal 4-methylsulfonyl-2,6-dinitro-n,n-substituted anilines |
US494268A US3321292A (en) | 1964-11-13 | 1965-10-08 | 4-methylsulfonyl-2, 6-dinitro-n, n-substituted anilines as herbicides |
Publications (1)
Publication Number | Publication Date |
---|---|
US3321292A true US3321292A (en) | 1967-05-23 |
Family
ID=27021284
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US411120A Expired - Lifetime US3227734A (en) | 1964-11-13 | 1964-11-13 | Herbicidal 4-methylsulfonyl-2,6-dinitro-n,n-substituted anilines |
US494268A Expired - Lifetime US3321292A (en) | 1964-11-13 | 1965-10-08 | 4-methylsulfonyl-2, 6-dinitro-n, n-substituted anilines as herbicides |
Family Applications Before (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US411120A Expired - Lifetime US3227734A (en) | 1964-11-13 | 1964-11-13 | Herbicidal 4-methylsulfonyl-2,6-dinitro-n,n-substituted anilines |
Country Status (10)
Country | Link |
---|---|
US (2) | US3227734A (en) |
BE (1) | BE672199A (en) |
BR (1) | BR6574766D0 (en) |
CH (1) | CH484608A (en) |
CS (1) | CS152423B2 (en) |
DE (1) | DE1518333C3 (en) |
DK (1) | DK117037B (en) |
GB (1) | GB1056199A (en) |
IL (1) | IL24613A (en) |
NL (1) | NL6510912A (en) |
Cited By (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3449111A (en) * | 1966-12-08 | 1969-06-10 | Lilly Co Eli | Method of eliminating weeds |
US3537840A (en) * | 1967-11-07 | 1970-11-03 | Uniroyal Inc | Synergistic herbicidal composition of sodium n-naphthyl phthalamic acid and 4 - (methylsulfonyl)-2,6-dinitro-n,n-dipropylaniline |
US3971650A (en) * | 1973-06-29 | 1976-07-27 | Chevron Research Company | Herbicidal N1 -methoxycarbonyl-N1 -alkyl-3,5-dinitro-N4 -N4 -dialkylsulfanilamide |
US3979203A (en) * | 1972-01-19 | 1976-09-07 | American Cyanamid Company | Sulfonamido herbicidal compositions and plant control methods using the same |
US3979453A (en) * | 1975-06-23 | 1976-09-07 | Eli Lilly And Company | 3-Cyanamino-2,6-dinitroanilines |
US4074059A (en) * | 1972-01-19 | 1978-02-14 | American Cyanamid Company | Substituted-1-phenol-4-sulfonamides |
US4227913A (en) * | 1971-06-30 | 1980-10-14 | American Cyanamid Company | Inhibiting plant bud growth with substituted 2,6-dinitroanilines |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3418101A (en) * | 1965-12-15 | 1968-12-24 | Pennsalt Chemicals Corp | Process for plant desiccation |
US3443927A (en) * | 1967-03-24 | 1969-05-13 | Rohm & Haas | Herbicidal mixture and method of controlling undesirable plant growth therewith |
DE1643719A1 (en) * | 1967-12-21 | 1971-01-28 | Basf Ag | Substituted dinitroanilines and herbicides containing them |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CA666837A (en) * | 1963-07-16 | Monsanto Chemical Company | Crab grass control | |
US3111403A (en) * | 1960-08-31 | 1963-11-19 | Lilly Co Eli | Herbicidal method |
US3124447A (en) * | 1964-03-10 | Herbicidal ratingxco n nveesion scale | ||
US3257190A (en) * | 1962-12-10 | 1966-06-21 | Lilly Co Eli | Method of eliminating weed grasses and broadleaf weeds |
Family Cites Families (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2053818A (en) * | 1935-03-21 | 1936-09-08 | Soc Of Chemical Ind | Azo-dyestuffs and process of making same |
US2938042A (en) * | 1956-02-03 | 1960-05-24 | Boots Pure Drug Co Ltd | Acyclic and aromatic sulphonylphenyl isothiocyanates |
NL268751A (en) * | 1960-08-31 |
-
1964
- 1964-11-13 US US411120A patent/US3227734A/en not_active Expired - Lifetime
-
1965
- 1965-08-20 NL NL6510912A patent/NL6510912A/xx unknown
- 1965-10-08 US US494268A patent/US3321292A/en not_active Expired - Lifetime
- 1965-11-10 BE BE672199D patent/BE672199A/xx not_active IP Right Cessation
- 1965-11-11 DE DE1518333A patent/DE1518333C3/en not_active Expired
- 1965-11-11 CS CS6737A patent/CS152423B2/cs unknown
- 1965-11-11 DK DK580965AA patent/DK117037B/en unknown
- 1965-11-11 BR BR174766/65A patent/BR6574766D0/en unknown
- 1965-11-11 CH CH1555765A patent/CH484608A/en not_active IP Right Cessation
- 1965-11-11 GB GB47914/65A patent/GB1056199A/en not_active Expired
- 1965-11-11 IL IL24613A patent/IL24613A/en unknown
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CA666837A (en) * | 1963-07-16 | Monsanto Chemical Company | Crab grass control | |
US3124447A (en) * | 1964-03-10 | Herbicidal ratingxco n nveesion scale | ||
US3111403A (en) * | 1960-08-31 | 1963-11-19 | Lilly Co Eli | Herbicidal method |
US3257190A (en) * | 1962-12-10 | 1966-06-21 | Lilly Co Eli | Method of eliminating weed grasses and broadleaf weeds |
Cited By (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3449111A (en) * | 1966-12-08 | 1969-06-10 | Lilly Co Eli | Method of eliminating weeds |
US3537840A (en) * | 1967-11-07 | 1970-11-03 | Uniroyal Inc | Synergistic herbicidal composition of sodium n-naphthyl phthalamic acid and 4 - (methylsulfonyl)-2,6-dinitro-n,n-dipropylaniline |
US4227913A (en) * | 1971-06-30 | 1980-10-14 | American Cyanamid Company | Inhibiting plant bud growth with substituted 2,6-dinitroanilines |
US3979203A (en) * | 1972-01-19 | 1976-09-07 | American Cyanamid Company | Sulfonamido herbicidal compositions and plant control methods using the same |
US4074059A (en) * | 1972-01-19 | 1978-02-14 | American Cyanamid Company | Substituted-1-phenol-4-sulfonamides |
US3971650A (en) * | 1973-06-29 | 1976-07-27 | Chevron Research Company | Herbicidal N1 -methoxycarbonyl-N1 -alkyl-3,5-dinitro-N4 -N4 -dialkylsulfanilamide |
US3979453A (en) * | 1975-06-23 | 1976-09-07 | Eli Lilly And Company | 3-Cyanamino-2,6-dinitroanilines |
Also Published As
Publication number | Publication date |
---|---|
IL24613A (en) | 1969-06-25 |
DE1518333B2 (en) | 1973-08-02 |
DE1518333C3 (en) | 1974-04-18 |
CH484608A (en) | 1970-01-31 |
BE672199A (en) | 1966-05-10 |
CS152423B2 (en) | 1973-12-19 |
DE1518333A1 (en) | 1971-09-02 |
GB1056199A (en) | 1967-01-25 |
BR6574766D0 (en) | 1973-08-16 |
DK117037B (en) | 1970-03-09 |
NL6510912A (en) | 1965-11-25 |
US3227734A (en) | 1966-01-04 |
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