US3235360A - Control of undesirable vegetation - Google Patents
Control of undesirable vegetation Download PDFInfo
- Publication number
- US3235360A US3235360A US232311A US23231162A US3235360A US 3235360 A US3235360 A US 3235360A US 232311 A US232311 A US 232311A US 23231162 A US23231162 A US 23231162A US 3235360 A US3235360 A US 3235360A
- Authority
- US
- United States
- Prior art keywords
- trimethyleneuracil
- salt
- carbon atoms
- alkyl
- butyl
- 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
- 150000001875 compounds Chemical class 0.000 claims description 65
- 238000000034 method Methods 0.000 claims description 19
- 239000000203 mixture Substances 0.000 description 72
- 125000004432 carbon atom Chemical group C* 0.000 description 71
- ISAKRJDGNUQOIC-UHFFFAOYSA-N Uracil Chemical compound O=C1C=CNC(=O)N1 ISAKRJDGNUQOIC-UHFFFAOYSA-N 0.000 description 62
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 58
- -1 Ethanolamine Dodecylamine Ethylenediamine Hexamethylenediamine Chemical compound 0.000 description 49
- 125000000217 alkyl group Chemical group 0.000 description 37
- 241000196324 Embryophyta Species 0.000 description 35
- 239000000243 solution Substances 0.000 description 33
- 238000009472 formulation Methods 0.000 description 31
- 229940035893 uracil Drugs 0.000 description 31
- 239000008187 granular material Substances 0.000 description 29
- 150000003839 salts Chemical class 0.000 description 29
- 239000004480 active ingredient Substances 0.000 description 27
- 230000002363 herbicidal effect Effects 0.000 description 25
- 235000014716 Eleusine indica Nutrition 0.000 description 24
- 239000004927 clay Substances 0.000 description 24
- 235000001602 Digitaria X umfolozi Nutrition 0.000 description 22
- 235000017898 Digitaria ciliaris Nutrition 0.000 description 22
- 235000005476 Digitaria cruciata Nutrition 0.000 description 22
- 235000006830 Digitaria didactyla Nutrition 0.000 description 22
- 235000005804 Digitaria eriantha ssp. eriantha Nutrition 0.000 description 22
- 235000010823 Digitaria sanguinalis Nutrition 0.000 description 22
- 244000025670 Eleusine indica Species 0.000 description 22
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 22
- 239000002245 particle Substances 0.000 description 22
- 238000002360 preparation method Methods 0.000 description 20
- 159000000000 sodium salts Chemical class 0.000 description 20
- 235000009344 Chenopodium album Nutrition 0.000 description 19
- 239000003921 oil Substances 0.000 description 19
- 239000004563 wettable powder Substances 0.000 description 19
- 239000000460 chlorine Substances 0.000 description 18
- 229910052801 chlorine Inorganic materials 0.000 description 18
- 239000007787 solid Substances 0.000 description 18
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 17
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 16
- 238000002156 mixing Methods 0.000 description 16
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 15
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 15
- 229910052794 bromium Inorganic materials 0.000 description 15
- 244000036975 Ambrosia artemisiifolia Species 0.000 description 14
- 235000003129 Ambrosia artemisiifolia var elatior Nutrition 0.000 description 14
- 235000003484 annual ragweed Nutrition 0.000 description 14
- 235000006263 bur ragweed Nutrition 0.000 description 14
- 235000003488 common ragweed Nutrition 0.000 description 14
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 14
- 235000009736 ragweed Nutrition 0.000 description 14
- 239000002904 solvent Substances 0.000 description 14
- 125000001424 substituent group Chemical group 0.000 description 14
- 229960000892 attapulgite Drugs 0.000 description 13
- 239000004615 ingredient Substances 0.000 description 13
- 229910052625 palygorskite Inorganic materials 0.000 description 13
- 235000009328 Amaranthus caudatus Nutrition 0.000 description 12
- 240000001592 Amaranthus caudatus Species 0.000 description 12
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 12
- 150000001412 amines Chemical class 0.000 description 12
- 240000006122 Chenopodium album Species 0.000 description 11
- 244000058871 Echinochloa crus-galli Species 0.000 description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
- ZTMKADLOSYKWCA-UHFFFAOYSA-N lenacil Chemical compound O=C1NC=2CCCC=2C(=O)N1C1CCCCC1 ZTMKADLOSYKWCA-UHFFFAOYSA-N 0.000 description 11
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 10
- 240000002439 Sorghum halepense Species 0.000 description 10
- 239000002585 base Substances 0.000 description 10
- 239000004009 herbicide Substances 0.000 description 10
- 239000008188 pellet Substances 0.000 description 10
- 239000000725 suspension Substances 0.000 description 10
- 235000013479 Amaranthus retroflexus Nutrition 0.000 description 9
- 244000237956 Amaranthus retroflexus Species 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- YDEXUEFDPVHGHE-GGMCWBHBSA-L disodium;(2r)-3-(2-hydroxy-3-methoxyphenyl)-2-[2-methoxy-4-(3-sulfonatopropyl)phenoxy]propane-1-sulfonate Chemical compound [Na+].[Na+].COC1=CC=CC(C[C@H](CS([O-])(=O)=O)OC=2C(=CC(CCCS([O-])(=O)=O)=CC=2)OC)=C1O YDEXUEFDPVHGHE-GGMCWBHBSA-L 0.000 description 9
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 9
- 235000004135 Amaranthus viridis Nutrition 0.000 description 8
- 235000005484 Chenopodium berlandieri Nutrition 0.000 description 8
- 235000009332 Chenopodium rubrum Nutrition 0.000 description 8
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 8
- 239000002253 acid Substances 0.000 description 8
- 125000003710 aryl alkyl group Chemical group 0.000 description 8
- 235000013877 carbamide Nutrition 0.000 description 8
- 239000007788 liquid Substances 0.000 description 8
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 8
- 239000004094 surface-active agent Substances 0.000 description 8
- 229950000329 thiouracil Drugs 0.000 description 8
- 240000006995 Abutilon theophrasti Species 0.000 description 7
- 235000012629 Mentha aquatica Nutrition 0.000 description 7
- 235000015225 Panicum colonum Nutrition 0.000 description 7
- 240000000275 Persicaria hydropiper Species 0.000 description 7
- 235000017337 Persicaria hydropiper Nutrition 0.000 description 7
- 235000004442 Polygonum persicaria Nutrition 0.000 description 7
- 125000000392 cycloalkenyl group Chemical group 0.000 description 7
- 150000002148 esters Chemical class 0.000 description 7
- 239000007921 spray Substances 0.000 description 7
- 150000003672 ureas Chemical class 0.000 description 7
- 241001148727 Bromus tectorum Species 0.000 description 6
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 6
- 235000003403 Limnocharis flava Nutrition 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 235000002595 Solanum tuberosum Nutrition 0.000 description 6
- 244000061456 Solanum tuberosum Species 0.000 description 6
- 244000197975 Solidago virgaurea Species 0.000 description 6
- 235000000914 Solidago virgaurea Nutrition 0.000 description 6
- 125000003545 alkoxy group Chemical group 0.000 description 6
- 239000004202 carbamide Substances 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- GUJOJGAPFQRJSV-UHFFFAOYSA-N dialuminum;dioxosilane;oxygen(2-);hydrate Chemical compound O.[O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O GUJOJGAPFQRJSV-UHFFFAOYSA-N 0.000 description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 6
- IZUPBVBPLAPZRR-UHFFFAOYSA-N pentachlorophenol Chemical compound OC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl IZUPBVBPLAPZRR-UHFFFAOYSA-N 0.000 description 6
- 150000002989 phenols Chemical class 0.000 description 6
- 235000012015 potatoes Nutrition 0.000 description 6
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 6
- WXNZTHHGJRFXKQ-UHFFFAOYSA-N 4-chlorophenol Chemical compound OC1=CC=C(Cl)C=C1 WXNZTHHGJRFXKQ-UHFFFAOYSA-N 0.000 description 5
- 244000003416 Asparagus officinalis Species 0.000 description 5
- 235000005340 Asparagus officinalis Nutrition 0.000 description 5
- 235000011292 Brassica rapa Nutrition 0.000 description 5
- 235000004977 Brassica sinapistrum Nutrition 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 240000007807 Sisymbrium officinale Species 0.000 description 5
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 5
- 239000011149 active material Substances 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 5
- 239000000440 bentonite Substances 0.000 description 5
- 229910000278 bentonite Inorganic materials 0.000 description 5
- 125000004093 cyano group Chemical group *C#N 0.000 description 5
- 229910003002 lithium salt Inorganic materials 0.000 description 5
- 159000000002 lithium salts Chemical class 0.000 description 5
- 229920000609 methyl cellulose Polymers 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- 239000001923 methylcellulose Substances 0.000 description 5
- 235000010981 methylcellulose Nutrition 0.000 description 5
- 239000003208 petroleum Substances 0.000 description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 239000011734 sodium Substances 0.000 description 5
- 229910052708 sodium Inorganic materials 0.000 description 5
- 125000005346 substituted cycloalkyl group Chemical group 0.000 description 5
- 241000205585 Aquilegia canadensis Species 0.000 description 4
- 229920000742 Cotton Polymers 0.000 description 4
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 4
- 240000003173 Drymaria cordata Species 0.000 description 4
- 240000005702 Galium aparine Species 0.000 description 4
- 235000014820 Galium aparine Nutrition 0.000 description 4
- 244000299507 Gossypium hirsutum Species 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 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 4
- 240000001549 Ipomoea eriocarpa Species 0.000 description 4
- 235000005146 Ipomoea eriocarpa Nutrition 0.000 description 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
- 241001148659 Panicum dichotomiflorum Species 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 4
- 244000292693 Poa annua Species 0.000 description 4
- 241001092459 Rubus Species 0.000 description 4
- 235000017848 Rubus fruticosus Nutrition 0.000 description 4
- 240000000111 Saccharum officinarum Species 0.000 description 4
- 235000007201 Saccharum officinarum Nutrition 0.000 description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 4
- 125000003342 alkenyl group Chemical group 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
- 159000000009 barium salts Chemical class 0.000 description 4
- YOUGRGFIHBUKRS-UHFFFAOYSA-N benzyl(trimethyl)azanium Chemical class C[N+](C)(C)CC1=CC=CC=C1 YOUGRGFIHBUKRS-UHFFFAOYSA-N 0.000 description 4
- 239000011575 calcium Substances 0.000 description 4
- 229910052791 calcium Inorganic materials 0.000 description 4
- 239000012141 concentrate Substances 0.000 description 4
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 description 4
- 239000002283 diesel fuel Substances 0.000 description 4
- 235000019329 dioctyl sodium sulphosuccinate Nutrition 0.000 description 4
- 235000019441 ethanol Nutrition 0.000 description 4
- 125000004494 ethyl ester group Chemical group 0.000 description 4
- 229930195733 hydrocarbon Natural products 0.000 description 4
- 150000002430 hydrocarbons Chemical class 0.000 description 4
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 4
- 239000011777 magnesium Substances 0.000 description 4
- 229910052749 magnesium Inorganic materials 0.000 description 4
- 229910052760 oxygen Inorganic materials 0.000 description 4
- 239000001301 oxygen Substances 0.000 description 4
- LZMATGARSSLFMQ-UHFFFAOYSA-N propan-2-ylurea Chemical compound CC(C)NC(N)=O LZMATGARSSLFMQ-UHFFFAOYSA-N 0.000 description 4
- 150000003254 radicals Chemical class 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 239000002002 slurry Substances 0.000 description 4
- RPACBEVZENYWOL-XFULWGLBSA-M sodium;(2r)-2-[6-(4-chlorophenoxy)hexyl]oxirane-2-carboxylate Chemical compound [Na+].C=1C=C(Cl)C=CC=1OCCCCCC[C@]1(C(=O)[O-])CO1 RPACBEVZENYWOL-XFULWGLBSA-M 0.000 description 4
- 238000005507 spraying Methods 0.000 description 4
- 125000000547 substituted alkyl group Chemical group 0.000 description 4
- 125000003107 substituted aryl group Chemical group 0.000 description 4
- 239000011593 sulfur Chemical group 0.000 description 4
- 229910052717 sulfur Chemical group 0.000 description 4
- QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical class C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 description 4
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical class NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 4
- 239000008096 xylene Substances 0.000 description 4
- CDOUZKKFHVEKRI-UHFFFAOYSA-N 3-bromo-n-[(prop-2-enoylamino)methyl]propanamide Chemical compound BrCCC(=O)NCNC(=O)C=C CDOUZKKFHVEKRI-UHFFFAOYSA-N 0.000 description 3
- 241001143500 Aceraceae Species 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 239000005995 Aluminium silicate Substances 0.000 description 3
- 241001327399 Andropogon gerardii Species 0.000 description 3
- 241000219310 Beta vulgaris subsp. vulgaris Species 0.000 description 3
- 244000104272 Bidens pilosa Species 0.000 description 3
- 241000219198 Brassica Species 0.000 description 3
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 3
- 239000004215 Carbon black (E152) Substances 0.000 description 3
- 244000052363 Cynodon dactylon Species 0.000 description 3
- 241000508725 Elymus repens Species 0.000 description 3
- 241000277301 Esociformes Species 0.000 description 3
- 235000009198 Lamium amplexicaule Nutrition 0.000 description 3
- 244000303225 Lamium amplexicaule Species 0.000 description 3
- 241000208682 Liquidambar Species 0.000 description 3
- 235000006552 Liquidambar styraciflua Nutrition 0.000 description 3
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 3
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 3
- 235000003805 Musa ABB Group Nutrition 0.000 description 3
- 240000005561 Musa balbisiana Species 0.000 description 3
- 235000015266 Plantago major Nutrition 0.000 description 3
- 241000209504 Poaceae Species 0.000 description 3
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 3
- 244000234609 Portulaca oleracea Species 0.000 description 3
- 235000001855 Portulaca oleracea Nutrition 0.000 description 3
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 241000159243 Toxicodendron radicans Species 0.000 description 3
- 244000067505 Xanthium strumarium Species 0.000 description 3
- 125000000304 alkynyl group Chemical group 0.000 description 3
- 235000012211 aluminium silicate Nutrition 0.000 description 3
- 229910052788 barium Inorganic materials 0.000 description 3
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 3
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 description 3
- 150000007942 carboxylates Chemical group 0.000 description 3
- 125000000753 cycloalkyl group Chemical group 0.000 description 3
- 239000006185 dispersion Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000001125 extrusion Methods 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 229910052742 iron Inorganic materials 0.000 description 3
- 229910052744 lithium Inorganic materials 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 229910052901 montmorillonite Inorganic materials 0.000 description 3
- 229910052700 potassium Inorganic materials 0.000 description 3
- 239000011591 potassium Substances 0.000 description 3
- 125000001453 quaternary ammonium group Chemical group 0.000 description 3
- 229910052938 sodium sulfate Inorganic materials 0.000 description 3
- 235000011152 sodium sulphate Nutrition 0.000 description 3
- 229910052712 strontium Inorganic materials 0.000 description 3
- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 description 3
- 150000003871 sulfonates Chemical class 0.000 description 3
- 230000008961 swelling Effects 0.000 description 3
- VNMLVHLVBFHHSN-UHFFFAOYSA-N thiophen-2-ylcarbamic acid Chemical compound OC(=O)NC1=CC=CS1 VNMLVHLVBFHHSN-UHFFFAOYSA-N 0.000 description 3
- GXEKYRXVRROBEV-FBXFSONDSA-N (1r,2s,3r,4s)-7-oxabicyclo[2.2.1]heptane-2,3-dicarboxylic acid Chemical compound C1C[C@@H]2[C@@H](C(O)=O)[C@@H](C(=O)O)[C@H]1O2 GXEKYRXVRROBEV-FBXFSONDSA-N 0.000 description 2
- UVMTZTPUIFOAGM-UHFFFAOYSA-N (3-chlorophenyl)carbamic acid Chemical compound OC(=O)NC1=CC=CC(Cl)=C1 UVMTZTPUIFOAGM-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- HFZWRUODUSTPEG-UHFFFAOYSA-N 2,4-dichlorophenol Chemical compound OC1=CC=C(Cl)C=C1Cl HFZWRUODUSTPEG-UHFFFAOYSA-N 0.000 description 2
- BZSXEZOLBIJVQK-UHFFFAOYSA-N 2-methylsulfonylbenzoic acid Chemical compound CS(=O)(=O)C1=CC=CC=C1C(O)=O BZSXEZOLBIJVQK-UHFFFAOYSA-N 0.000 description 2
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 description 2
- VXARUOXETPLQOW-UHFFFAOYSA-N 5-bromo-3-cyclohexyl-6-methyl-1h-pyrimidine-2,4-dione Chemical compound O=C1C(Br)=C(C)NC(=O)N1C1CCCCC1 VXARUOXETPLQOW-UHFFFAOYSA-N 0.000 description 2
- OSYDJUPAOGYUHN-UHFFFAOYSA-N 5-methylidenepyrimidine-2,4-dione Chemical compound C=C1C=NC(=O)NC1=O OSYDJUPAOGYUHN-UHFFFAOYSA-N 0.000 description 2
- 244000296912 Ageratum conyzoides Species 0.000 description 2
- 235000004405 Ageratum conyzoides Nutrition 0.000 description 2
- 244000099147 Ananas comosus Species 0.000 description 2
- 235000007119 Ananas comosus Nutrition 0.000 description 2
- 241000803625 Andropogon virginicus Species 0.000 description 2
- 235000021537 Beetroot Nutrition 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 2
- 235000003351 Brassica cretica Nutrition 0.000 description 2
- 235000003343 Brassica rupestris Nutrition 0.000 description 2
- PJINIBMAHRTKNZ-UHFFFAOYSA-N CC(CCCCCCCCOCCCCCCCCC(C)(C)C)(C)C Chemical compound CC(CCCCCCCCOCCCCCCCCC(C)(C)C)(C)C PJINIBMAHRTKNZ-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- 241000217446 Calystegia sepium Species 0.000 description 2
- 235000016535 Capraria biflora Nutrition 0.000 description 2
- 235000011305 Capsella bursa pastoris Nutrition 0.000 description 2
- 240000008867 Capsella bursa-pastoris Species 0.000 description 2
- 229940126062 Compound A Drugs 0.000 description 2
- 244000000626 Daucus carota Species 0.000 description 2
- 235000002206 Daucus carota subsp carota Nutrition 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 2
- 241001599881 Euphorbia maculata Species 0.000 description 2
- 241001618883 Euphorbia uralensis Species 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 2
- 235000017335 Hordeum vulgare subsp spontaneum Nutrition 0.000 description 2
- 241001299819 Hordeum vulgare subsp. spontaneum Species 0.000 description 2
- 235000017309 Hypericum perforatum Nutrition 0.000 description 2
- 241000209082 Lolium Species 0.000 description 2
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 description 2
- 241000282320 Panthera leo Species 0.000 description 2
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- 239000004372 Polyvinyl alcohol Substances 0.000 description 2
- 241000219492 Quercus Species 0.000 description 2
- 244000057899 Rudbeckia hirta var. pulcherrima Species 0.000 description 2
- 244000124765 Salsola kali Species 0.000 description 2
- 235000007658 Salsola kali Nutrition 0.000 description 2
- 235000017016 Setaria faberi Nutrition 0.000 description 2
- 241000820191 Setaria magna Species 0.000 description 2
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 2
- 235000009337 Spinacia oleracea Nutrition 0.000 description 2
- 244000300264 Spinacia oleracea Species 0.000 description 2
- 235000021536 Sugar beet Nutrition 0.000 description 2
- 208000027418 Wounds and injury Diseases 0.000 description 2
- 239000003377 acid catalyst Substances 0.000 description 2
- 238000013019 agitation Methods 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- 239000000908 ammonium hydroxide Substances 0.000 description 2
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- 235000005770 birds nest Nutrition 0.000 description 2
- QKSKPIVNLNLAAV-UHFFFAOYSA-N bis(2-chloroethyl) sulfide Chemical compound ClCCSCCCl QKSKPIVNLNLAAV-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 159000000007 calcium salts Chemical class 0.000 description 2
- 150000001733 carboxylic acid esters Chemical class 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- 150000001768 cations Chemical class 0.000 description 2
- 238000003181 co-melting Methods 0.000 description 2
- 230000007797 corrosion Effects 0.000 description 2
- 238000005260 corrosion Methods 0.000 description 2
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 2
- 230000006378 damage Effects 0.000 description 2
- 125000004663 dialkyl amino group Chemical group 0.000 description 2
- OGGXGZAMXPVRFZ-UHFFFAOYSA-N dimethylarsinic acid Chemical compound C[As](C)(O)=O OGGXGZAMXPVRFZ-UHFFFAOYSA-N 0.000 description 2
- BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 description 2
- 229910000397 disodium phosphate Inorganic materials 0.000 description 2
- 235000019800 disodium phosphate Nutrition 0.000 description 2
- JRBPAEWTRLWTQC-UHFFFAOYSA-N dodecylamine Chemical class CCCCCCCCCCCCN JRBPAEWTRLWTQC-UHFFFAOYSA-N 0.000 description 2
- 239000003995 emulsifying agent Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 238000000227 grinding Methods 0.000 description 2
- 230000012010 growth Effects 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 2
- 150000004679 hydroxides Chemical class 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- 208000014674 injury Diseases 0.000 description 2
- 238000009434 installation Methods 0.000 description 2
- 150000002505 iron Chemical class 0.000 description 2
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 2
- 159000000003 magnesium salts Chemical class 0.000 description 2
- 229910052748 manganese Inorganic materials 0.000 description 2
- 239000011572 manganese Substances 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- 235000010460 mustard Nutrition 0.000 description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 2
- 239000004533 oil dispersion Substances 0.000 description 2
- 239000012053 oil suspension Substances 0.000 description 2
- IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- 229920002451 polyvinyl alcohol Polymers 0.000 description 2
- VPJDULFXCAQHRC-UHFFFAOYSA-N prop-2-enylurea Chemical compound NC(=O)NCC=C VPJDULFXCAQHRC-UHFFFAOYSA-N 0.000 description 2
- 238000006798 ring closing metathesis reaction Methods 0.000 description 2
- 239000004576 sand Substances 0.000 description 2
- BHRZNVHARXXAHW-UHFFFAOYSA-N sec-butylamine Chemical compound CCC(C)N BHRZNVHARXXAHW-UHFFFAOYSA-N 0.000 description 2
- WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 2
- 235000010234 sodium benzoate Nutrition 0.000 description 2
- 239000004299 sodium benzoate Substances 0.000 description 2
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 2
- NVIFVTYDZMXWGX-UHFFFAOYSA-N sodium metaborate Chemical compound [Na+].[O-]B=O NVIFVTYDZMXWGX-UHFFFAOYSA-N 0.000 description 2
- 239000001488 sodium phosphate Substances 0.000 description 2
- 239000008347 soybean phospholipid Substances 0.000 description 2
- 150000005846 sugar alcohols Polymers 0.000 description 2
- 239000003784 tall oil Substances 0.000 description 2
- DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical class CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 2
- VDZOOKBUILJEDG-UHFFFAOYSA-M tetrabutylammonium hydroxide Chemical compound [OH-].CCCC[N+](CCCC)(CCCC)CCCC VDZOOKBUILJEDG-UHFFFAOYSA-M 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 2
- 239000010455 vermiculite Substances 0.000 description 2
- 229910052902 vermiculite Inorganic materials 0.000 description 2
- 235000019354 vermiculite Nutrition 0.000 description 2
- 235000005765 wild carrot Nutrition 0.000 description 2
- ZWOULFZCQXICLZ-UHFFFAOYSA-N 1,3-dimethyl-1-phenylurea Chemical compound CNC(=O)N(C)C1=CC=CC=C1 ZWOULFZCQXICLZ-UHFFFAOYSA-N 0.000 description 1
- NDUPDOJHUQKPAG-UHFFFAOYSA-M 2,2-Dichloropropanoate Chemical compound CC(Cl)(Cl)C([O-])=O NDUPDOJHUQKPAG-UHFFFAOYSA-M 0.000 description 1
- NEBPTMCRLHKPOB-UHFFFAOYSA-N 2,2-diphenylacetonitrile Chemical compound C=1C=CC=CC=1C(C#N)C1=CC=CC=C1 NEBPTMCRLHKPOB-UHFFFAOYSA-N 0.000 description 1
- XZIDTOHMJBOSOX-UHFFFAOYSA-N 2,3,6-TBA Chemical compound OC(=O)C1=C(Cl)C=CC(Cl)=C1Cl XZIDTOHMJBOSOX-UHFFFAOYSA-N 0.000 description 1
- YOYAIZYFCNQIRF-UHFFFAOYSA-N 2,6-dichlorobenzonitrile Chemical compound ClC1=CC=CC(Cl)=C1C#N YOYAIZYFCNQIRF-UHFFFAOYSA-N 0.000 description 1
- OWZPCEFYPSAJFR-UHFFFAOYSA-N 2-(butan-2-yl)-4,6-dinitrophenol Chemical compound CCC(C)C1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1O OWZPCEFYPSAJFR-UHFFFAOYSA-N 0.000 description 1
- 125000004362 3,4,5-trichlorophenyl group Chemical group [H]C1=C(Cl)C(Cl)=C(Cl)C([H])=C1* 0.000 description 1
- XMTQQYYKAHVGBJ-UHFFFAOYSA-N 3-(3,4-DICHLOROPHENYL)-1,1-DIMETHYLUREA Chemical compound CN(C)C(=O)NC1=CC=C(Cl)C(Cl)=C1 XMTQQYYKAHVGBJ-UHFFFAOYSA-N 0.000 description 1
- XCFNVOSYXPYRBG-UHFFFAOYSA-N 3-(4-chloro-2-phenoxyphenyl)-1,1-dimethylurea Chemical compound CN(C)C(=O)NC1=CC=C(Cl)C=C1OC1=CC=CC=C1 XCFNVOSYXPYRBG-UHFFFAOYSA-N 0.000 description 1
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 description 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 1
- BTJIUGUIPKRLHP-UHFFFAOYSA-N 4-nitrophenol Chemical compound OC1=CC=C([N+]([O-])=O)C=C1 BTJIUGUIPKRLHP-UHFFFAOYSA-N 0.000 description 1
- ZYUVGYBAPZYKSA-UHFFFAOYSA-N 5-(3-hydroxybutan-2-yl)-4-methylbenzene-1,3-diol Chemical compound CC(O)C(C)C1=CC(O)=CC(O)=C1C ZYUVGYBAPZYKSA-UHFFFAOYSA-N 0.000 description 1
- DSFXMGCKOKZNCS-UHFFFAOYSA-N 5-bromo-3-propan-2-yl-1h-pyrimidine-2,4-dione Chemical compound CC(C)N1C(=O)NC=C(Br)C1=O DSFXMGCKOKZNCS-UHFFFAOYSA-N 0.000 description 1
- YFGKIDJUAOXMAL-UHFFFAOYSA-N 6-methylheptylurea Chemical compound C(CCCCC(C)C)NC(=O)N YFGKIDJUAOXMAL-UHFFFAOYSA-N 0.000 description 1
- 240000005020 Acaciella glauca Species 0.000 description 1
- 240000000073 Achillea millefolium Species 0.000 description 1
- 235000007754 Achillea millefolium Nutrition 0.000 description 1
- MDBGGTQNNUOQRC-UHFFFAOYSA-N Allidochlor Chemical compound ClCC(=O)N(CC=C)CC=C MDBGGTQNNUOQRC-UHFFFAOYSA-N 0.000 description 1
- KLSJWNVTNUYHDU-UHFFFAOYSA-N Amitrole Chemical compound NC1=NC=NN1 KLSJWNVTNUYHDU-UHFFFAOYSA-N 0.000 description 1
- GEHMBYLTCISYNY-UHFFFAOYSA-N Ammonium sulfamate Chemical compound [NH4+].NS([O-])(=O)=O GEHMBYLTCISYNY-UHFFFAOYSA-N 0.000 description 1
- 244000251090 Anthemis cotula Species 0.000 description 1
- 235000007639 Anthemis cotula Nutrition 0.000 description 1
- 241000722948 Apocynum cannabinum Species 0.000 description 1
- 244000105624 Arachis hypogaea Species 0.000 description 1
- 240000005528 Arctium lappa Species 0.000 description 1
- 235000003130 Arctium lappa Nutrition 0.000 description 1
- 235000008078 Arctium minus Nutrition 0.000 description 1
- 235000007320 Avena fatua Nutrition 0.000 description 1
- 244000075850 Avena orientalis Species 0.000 description 1
- 241000490495 Barbarea Species 0.000 description 1
- 235000007563 Barbarea vulgaris Nutrition 0.000 description 1
- 241000143476 Bidens Species 0.000 description 1
- 235000010662 Bidens pilosa Nutrition 0.000 description 1
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 1
- 241000209202 Bromus secalinus Species 0.000 description 1
- NUZMSDTXKGOPFU-UHFFFAOYSA-N C1(CCCCC1)N1C(NC(=CC1=O)CC)=O.C1(CCCCC1)N1C(NC(=CC1=O)C)=O Chemical compound C1(CCCCC1)N1C(NC(=CC1=O)CC)=O.C1(CCCCC1)N1C(NC(=CC1=O)C)=O NUZMSDTXKGOPFU-UHFFFAOYSA-N 0.000 description 1
- RMBBSOLAGVEUSI-UHFFFAOYSA-H Calcium arsenate Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-][As]([O-])([O-])=O.[O-][As]([O-])([O-])=O RMBBSOLAGVEUSI-UHFFFAOYSA-H 0.000 description 1
- 235000003255 Carthamus tinctorius Nutrition 0.000 description 1
- 244000020518 Carthamus tinctorius Species 0.000 description 1
- 235000005633 Chrysanthemum balsamita Nutrition 0.000 description 1
- 244000260524 Chrysanthemum balsamita Species 0.000 description 1
- 235000008733 Citrus aurantifolia Nutrition 0.000 description 1
- BVKRDAXJHAHNAF-UHFFFAOYSA-N ClC=1C=C(C=CC1Cl)N(C(N(C)C)=O)C.ClC1=CC=C(C=C1)NC(N(C)OC)=O Chemical compound ClC=1C=C(C=CC1Cl)N(C(N(C)C)=O)C.ClC1=CC=C(C=C1)NC(N(C)OC)=O BVKRDAXJHAHNAF-UHFFFAOYSA-N 0.000 description 1
- 235000013162 Cocos nucifera Nutrition 0.000 description 1
- 244000060011 Cocos nucifera Species 0.000 description 1
- 244000074881 Conyza canadensis Species 0.000 description 1
- 235000004385 Conyza canadensis Nutrition 0.000 description 1
- NPOJQCVWMSKXDN-UHFFFAOYSA-N Dacthal Chemical compound COC(=O)C1=C(Cl)C(Cl)=C(C(=O)OC)C(Cl)=C1Cl NPOJQCVWMSKXDN-UHFFFAOYSA-N 0.000 description 1
- 229920001353 Dextrin Polymers 0.000 description 1
- 239000004375 Dextrin Substances 0.000 description 1
- 239000001692 EU approved anti-caking agent Substances 0.000 description 1
- 235000016164 Elymus triticoides Nutrition 0.000 description 1
- 240000003759 Erodium cicutarium Species 0.000 description 1
- 235000005608 Erodium cicutarium subsp. bipinnatum Nutrition 0.000 description 1
- 235000000187 Erodium cicutarium subsp. cicutarium Nutrition 0.000 description 1
- 235000000190 Erodium cicutarium subsp. jacquinianum Nutrition 0.000 description 1
- ZLSWBLPERHFHIS-UHFFFAOYSA-N Fenoprop Chemical compound OC(=O)C(C)OC1=CC(Cl)=C(Cl)C=C1Cl ZLSWBLPERHFHIS-UHFFFAOYSA-N 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- 235000010469 Glycine max Nutrition 0.000 description 1
- 244000068988 Glycine max Species 0.000 description 1
- 241001075721 Hibiscus trionum Species 0.000 description 1
- 235000001047 Hibiscus trionum Nutrition 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 235000009714 Hyptis pectinata Nutrition 0.000 description 1
- PSYBGEADHLUXCS-UHFFFAOYSA-N Isocil Chemical compound CC(C)N1C(=O)NC(C)=C(Br)C1=O PSYBGEADHLUXCS-UHFFFAOYSA-N 0.000 description 1
- 240000007049 Juglans regia Species 0.000 description 1
- 235000009496 Juglans regia Nutrition 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- 235000003127 Lactuca serriola Nutrition 0.000 description 1
- 240000006137 Lactuca serriola Species 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- 241000511731 Leymus Species 0.000 description 1
- 244000100545 Lolium multiflorum Species 0.000 description 1
- BGRDGMRNKXEXQD-UHFFFAOYSA-N Maleic hydrazide Chemical compound OC1=CC=C(O)N=N1 BGRDGMRNKXEXQD-UHFFFAOYSA-N 0.000 description 1
- 239000005983 Maleic hydrazide Substances 0.000 description 1
- 235000000060 Malva neglecta Nutrition 0.000 description 1
- 240000004658 Medicago sativa Species 0.000 description 1
- 235000017587 Medicago sativa ssp. sativa 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
- 235000009382 Mollugo verticillata Nutrition 0.000 description 1
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 1
- MOQIDTUQXZJMPO-UHFFFAOYSA-N N1C(=O)NC(=O)C=C1.C1(=CC=CC=C1)O Chemical class N1C(=O)NC(=O)C=C1.C1(=CC=CC=C1)O MOQIDTUQXZJMPO-UHFFFAOYSA-N 0.000 description 1
- 101100114416 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) con-10 gene Proteins 0.000 description 1
- 244000227633 Ocotea pretiosa Species 0.000 description 1
- 235000004263 Ocotea pretiosa Nutrition 0.000 description 1
- 244000119329 Osmunda cinnamomea Species 0.000 description 1
- 235000007889 Osmunda cinnamomea Nutrition 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 241000209117 Panicum Species 0.000 description 1
- 241001465363 Panicum capillare Species 0.000 description 1
- 240000004928 Paspalum scrobiculatum Species 0.000 description 1
- 235000003675 Paspalum scrobiculatum Nutrition 0.000 description 1
- 241000745991 Phalaris Species 0.000 description 1
- 235000005632 Phalaris canariensis Nutrition 0.000 description 1
- 241000226265 Phanopyrum Species 0.000 description 1
- CXOFVDLJLONNDW-UHFFFAOYSA-N Phenytoin Chemical group N1C(=O)NC(=O)C1(C=1C=CC=CC=1)C1=CC=CC=C1 CXOFVDLJLONNDW-UHFFFAOYSA-N 0.000 description 1
- 240000005218 Phyla nodiflora Species 0.000 description 1
- 235000010503 Plantago lanceolata Nutrition 0.000 description 1
- 244000292697 Polygonum aviculare Species 0.000 description 1
- 235000006386 Polygonum aviculare Nutrition 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- 241000219295 Portulaca Species 0.000 description 1
- 244000082988 Secale cereale Species 0.000 description 1
- 235000002248 Setaria viridis Nutrition 0.000 description 1
- 240000003461 Setaria viridis Species 0.000 description 1
- 235000010086 Setaria viridis var. viridis Nutrition 0.000 description 1
- 239000004115 Sodium Silicate Substances 0.000 description 1
- 235000002594 Solanum nigrum Nutrition 0.000 description 1
- 240000002307 Solanum ptychanthum Species 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- SAQSTQBVENFSKT-UHFFFAOYSA-M TCA-sodium Chemical compound [Na+].[O-]C(=O)C(Cl)(Cl)Cl SAQSTQBVENFSKT-UHFFFAOYSA-M 0.000 description 1
- 240000001949 Taraxacum officinale Species 0.000 description 1
- 235000005187 Taraxacum officinale ssp. officinale Nutrition 0.000 description 1
- 244000152045 Themeda triandra Species 0.000 description 1
- 235000008214 Thlaspi arvense Nutrition 0.000 description 1
- 240000008488 Thlaspi arvense Species 0.000 description 1
- 235000011941 Tilia x europaea Nutrition 0.000 description 1
- 235000021307 Triticum Nutrition 0.000 description 1
- 244000098338 Triticum aestivum Species 0.000 description 1
- 241001106462 Ulmus Species 0.000 description 1
- 241000335654 Uracis Species 0.000 description 1
- 235000005373 Uvularia sessilifolia Nutrition 0.000 description 1
- 244000041519 Verbena bonariensis Species 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 1
- 125000006307 alkoxy benzyl group Chemical group 0.000 description 1
- 125000005078 alkoxycarbonylalkyl group Chemical group 0.000 description 1
- 125000002877 alkyl aryl group Chemical group 0.000 description 1
- 125000006177 alkyl benzyl group Chemical group 0.000 description 1
- HTKFORQRBXIQHD-UHFFFAOYSA-N allylthiourea Chemical compound NC(=S)NCC=C HTKFORQRBXIQHD-UHFFFAOYSA-N 0.000 description 1
- 150000001409 amidines Chemical class 0.000 description 1
- SOIFLUNRINLCBN-UHFFFAOYSA-N ammonium thiocyanate Chemical compound [NH4+].[S-]C#N SOIFLUNRINLCBN-UHFFFAOYSA-N 0.000 description 1
- 239000002518 antifoaming agent Substances 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- MXWJVTOOROXGIU-UHFFFAOYSA-N atrazine Chemical compound CCNC1=NC(Cl)=NC(NC(C)C)=N1 MXWJVTOOROXGIU-UHFFFAOYSA-N 0.000 description 1
- WDIHJSXYQDMJHN-UHFFFAOYSA-L barium chloride Chemical compound [Cl-].[Cl-].[Ba+2] WDIHJSXYQDMJHN-UHFFFAOYSA-L 0.000 description 1
- 229910001626 barium chloride Inorganic materials 0.000 description 1
- PWHCIQQGOQTFAE-UHFFFAOYSA-L barium chloride dihydrate Chemical compound O.O.[Cl-].[Cl-].[Ba+2] PWHCIQQGOQTFAE-UHFFFAOYSA-L 0.000 description 1
- 239000003637 basic solution Substances 0.000 description 1
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
- 229910021538 borax Inorganic materials 0.000 description 1
- CNWSQCLBDWYLAN-UHFFFAOYSA-N butylurea Chemical compound CCCCNC(N)=O CNWSQCLBDWYLAN-UHFFFAOYSA-N 0.000 description 1
- 229950004243 cacodylic acid Drugs 0.000 description 1
- 229940103357 calcium arsenate Drugs 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 235000010216 calcium carbonate Nutrition 0.000 description 1
- 239000001506 calcium phosphate Substances 0.000 description 1
- 229910000389 calcium phosphate Inorganic materials 0.000 description 1
- 235000011010 calcium phosphates Nutrition 0.000 description 1
- BBADVFYXEMLJKM-UHFFFAOYSA-L calcium;dioxido-oxo-propyl-$l^{5}-arsane Chemical compound [Ca+2].CCC[As]([O-])([O-])=O BBADVFYXEMLJKM-UHFFFAOYSA-L 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- QZXCCPZJCKEPSA-UHFFFAOYSA-N chlorfenac Chemical compound OC(=O)CC1=C(Cl)C=CC(Cl)=C1Cl QZXCCPZJCKEPSA-UHFFFAOYSA-N 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 1
- 125000004965 chloroalkyl group Chemical group 0.000 description 1
- 125000004803 chlorobenzyl group Chemical group 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 125000004966 cyanoalkyl group Chemical group 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000001047 cyclobutenyl group Chemical group C1(=CCC1)* 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- WUESWDIHTKHGQA-UHFFFAOYSA-N cyclohexylurea Chemical compound NC(=O)NC1CCCCC1 WUESWDIHTKHGQA-UHFFFAOYSA-N 0.000 description 1
- DMODXKKZWDTRIU-UHFFFAOYSA-N cycloocten-1-ylurea Chemical compound C1(=CCCCCCC1)NC(=O)N DMODXKKZWDTRIU-UHFFFAOYSA-N 0.000 description 1
- 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- CBEYJGNJOCTQGW-UHFFFAOYSA-N cyclopentylurea Chemical compound NC(=O)NC1CCCC1 CBEYJGNJOCTQGW-UHFFFAOYSA-N 0.000 description 1
- IRQWLEOSDCDEHQ-UHFFFAOYSA-N cyclopropylmethylurea Chemical compound NC(=O)NCC1CC1 IRQWLEOSDCDEHQ-UHFFFAOYSA-N 0.000 description 1
- NHADDZMCASKINP-HTRCEHHLSA-N decarboxydihydrocitrinin Natural products C1=C(O)C(C)=C2[C@H](C)[C@@H](C)OCC2=C1O NHADDZMCASKINP-HTRCEHHLSA-N 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 235000019425 dextrin Nutrition 0.000 description 1
- 239000008121 dextrose Substances 0.000 description 1
- 125000004985 dialkyl amino alkyl group Chemical group 0.000 description 1
- JYIMWRSJCRRYNK-UHFFFAOYSA-N dialuminum;disodium;oxygen(2-);silicon(4+);hydrate Chemical compound O.[O-2].[O-2].[O-2].[O-2].[O-2].[O-2].[Na+].[Na+].[Al+3].[Al+3].[Si+4] JYIMWRSJCRRYNK-UHFFFAOYSA-N 0.000 description 1
- 125000006286 dichlorobenzyl group Chemical group 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- YHAIUSTWZPMYGG-UHFFFAOYSA-L disodium;2,2-dioctyl-3-sulfobutanedioate Chemical compound [Na+].[Na+].CCCCCCCCC(C([O-])=O)(C(C([O-])=O)S(O)(=O)=O)CCCCCCCC YHAIUSTWZPMYGG-UHFFFAOYSA-L 0.000 description 1
- UQGFMSUEHSUPRD-UHFFFAOYSA-N disodium;3,7-dioxido-2,4,6,8,9-pentaoxa-1,3,5,7-tetraborabicyclo[3.3.1]nonane Chemical compound [Na+].[Na+].O1B([O-])OB2OB([O-])OB1O2 UQGFMSUEHSUPRD-UHFFFAOYSA-N 0.000 description 1
- CDMADVZSLOHIFP-UHFFFAOYSA-N disodium;3,7-dioxido-2,4,6,8,9-pentaoxa-1,3,5,7-tetraborabicyclo[3.3.1]nonane;decahydrate Chemical compound O.O.O.O.O.O.O.O.O.O.[Na+].[Na+].O1B([O-])OB2OB([O-])OB1O2 CDMADVZSLOHIFP-UHFFFAOYSA-N 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- VICYBMUVWHJEFT-UHFFFAOYSA-N dodecyltrimethylammonium ion Chemical class CCCCCCCCCCCC[N+](C)(C)C VICYBMUVWHJEFT-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 150000002169 ethanolamines Chemical class 0.000 description 1
- JHZPNBKZPAWCJD-UHFFFAOYSA-N ethyl 2-oxocyclopentane-1-carboxylate Chemical compound CCOC(=O)C1CCCC1=O JHZPNBKZPAWCJD-UHFFFAOYSA-N 0.000 description 1
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- XXOYNJXVWVNOOJ-UHFFFAOYSA-N fenuron Chemical compound CN(C)C(=O)NC1=CC=CC=C1 XXOYNJXVWVNOOJ-UHFFFAOYSA-N 0.000 description 1
- 235000008384 feverfew Nutrition 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- 239000003292 glue Substances 0.000 description 1
- 150000002357 guanidines Chemical class 0.000 description 1
- 239000008233 hard water Substances 0.000 description 1
- 239000012456 homogeneous solution Substances 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- VDEGQTCMQUFPFH-UHFFFAOYSA-N hydroxy-dimethyl-arsine Natural products C[As](C)O VDEGQTCMQUFPFH-UHFFFAOYSA-N 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 229910052622 kaolinite Inorganic materials 0.000 description 1
- UWRBYRMOUPAKLM-UHFFFAOYSA-L lead arsenate Chemical compound [Pb+2].O[As]([O-])([O-])=O UWRBYRMOUPAKLM-UHFFFAOYSA-L 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 239000004571 lime Substances 0.000 description 1
- 239000012669 liquid formulation Substances 0.000 description 1
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
- 239000001095 magnesium carbonate Substances 0.000 description 1
- 229910000021 magnesium carbonate Inorganic materials 0.000 description 1
- 235000014380 magnesium carbonate Nutrition 0.000 description 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910001510 metal chloride Inorganic materials 0.000 description 1
- UCFFGYASXIPWPD-UHFFFAOYSA-N methyl hypochlorite Chemical compound COCl UCFFGYASXIPWPD-UHFFFAOYSA-N 0.000 description 1
- QYPPRTNMGCREIM-UHFFFAOYSA-N methylarsonic acid Chemical compound C[As](O)(O)=O QYPPRTNMGCREIM-UHFFFAOYSA-N 0.000 description 1
- 238000003801 milling Methods 0.000 description 1
- BMLIZLVNXIYGCK-UHFFFAOYSA-N monuron Chemical compound CN(C)C(=O)NC1=CC=C(Cl)C=C1 BMLIZLVNXIYGCK-UHFFFAOYSA-N 0.000 description 1
- PJFGPJQBWSEWKX-UHFFFAOYSA-N n-[(2,4-dichlorophenoxy)-methoxyphosphinothioyl]propan-2-amine Chemical compound CC(C)NP(=S)(OC)OC1=CC=C(Cl)C=C1Cl PJFGPJQBWSEWKX-UHFFFAOYSA-N 0.000 description 1
- 125000004923 naphthylmethyl group Chemical group C1(=CC=CC2=CC=CC=C12)C* 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 125000006502 nitrobenzyl group Chemical group 0.000 description 1
- 239000012454 non-polar solvent Substances 0.000 description 1
- 125000003518 norbornenyl group Chemical group C12(C=CC(CC1)C2)* 0.000 description 1
- 125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 0.000 description 1
- 239000010743 number 2 fuel oil Substances 0.000 description 1
- IOQPZZOEVPZRBK-UHFFFAOYSA-N octan-1-amine Chemical compound CCCCCCCCN IOQPZZOEVPZRBK-UHFFFAOYSA-N 0.000 description 1
- 125000004365 octenyl group Chemical group C(=CCCCCCC)* 0.000 description 1
- 125000002347 octyl 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])[H] 0.000 description 1
- UBBIDOUCHSVOFY-UHFFFAOYSA-N octylurea Chemical compound CCCCCCCCNC(N)=O UBBIDOUCHSVOFY-UHFFFAOYSA-N 0.000 description 1
- 239000004536 oil dispersible powder Substances 0.000 description 1
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 1
- 235000020232 peanut Nutrition 0.000 description 1
- VPOLVWCUBVJURT-UHFFFAOYSA-N pentadecasodium;pentaborate Chemical compound [Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[O-]B([O-])[O-].[O-]B([O-])[O-].[O-]B([O-])[O-].[O-]B([O-])[O-].[O-]B([O-])[O-] VPOLVWCUBVJURT-UHFFFAOYSA-N 0.000 description 1
- 230000000505 pernicious effect Effects 0.000 description 1
- 125000003884 phenylalkyl group Chemical group 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- VXPLXMJHHKHSOA-UHFFFAOYSA-N propham Chemical compound CC(C)OC(=O)NC1=CC=CC=C1 VXPLXMJHHKHSOA-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 229910052903 pyrophyllite Inorganic materials 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 235000003499 redwood Nutrition 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- PTLRDCMBXHILCL-UHFFFAOYSA-M sodium arsenite Chemical compound [Na+].[O-][As]=O PTLRDCMBXHILCL-UHFFFAOYSA-M 0.000 description 1
- 229940045998 sodium isethionate Drugs 0.000 description 1
- NTHWMYGWWRZVTN-UHFFFAOYSA-N sodium silicate Chemical compound [Na+].[Na+].[O-][Si]([O-])=O NTHWMYGWWRZVTN-UHFFFAOYSA-N 0.000 description 1
- 229910052911 sodium silicate Inorganic materials 0.000 description 1
- 235000010339 sodium tetraborate Nutrition 0.000 description 1
- 239000004328 sodium tetraborate Substances 0.000 description 1
- PDEFQWNXOUGDJR-UHFFFAOYSA-M sodium;2,2-dichloropropanoate Chemical compound [Na+].CC(Cl)(Cl)C([O-])=O PDEFQWNXOUGDJR-UHFFFAOYSA-M 0.000 description 1
- LADXKQRVAFSPTR-UHFFFAOYSA-M sodium;2-hydroxyethanesulfonate Chemical compound [Na+].OCCS([O-])(=O)=O LADXKQRVAFSPTR-UHFFFAOYSA-M 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 235000001508 sulfur Nutrition 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- CBXCPBUEXACCNR-UHFFFAOYSA-N tetraethylammonium Chemical class CC[N+](CC)(CC)CC CBXCPBUEXACCNR-UHFFFAOYSA-N 0.000 description 1
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 description 1
- OSBSFAARYOCBHB-UHFFFAOYSA-N tetrapropylammonium Chemical class CCC[N+](CCC)(CCC)CCC OSBSFAARYOCBHB-UHFFFAOYSA-N 0.000 description 1
- 150000003585 thioureas Chemical class 0.000 description 1
- 230000009974 thixotropic effect Effects 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
- 235000020234 walnut Nutrition 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/20—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D239/22—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/52—Two oxygen atoms
- C07D239/54—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
- C07D239/72—Quinazolines; Hydrogenated quinazolines
- C07D239/95—Quinazolines; Hydrogenated quinazolines with hetero atoms directly attached in positions 2 and 4
- C07D239/96—Two oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/645—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having two nitrogen atoms as the only ring hetero atoms
- C07F9/6509—Six-membered rings
- C07F9/6512—Six-membered rings having the nitrogen atoms in positions 1 and 3
Definitions
- this invention is directed to the herbicidal use of compounds of the formula 1 O O O u 1 RN RN m cro 2 Benin EX where R is alkyl of 1 through carbon atoms, substituted alkyl of 1 through 10 carbon atoms, aryl of 6 through 14 carbon atoms, substituted aryl of 6 through 14 carbon atoms, aralkyl of 7 through carbon atoms, substituted aralkyl of 7 through 15 carbon atoms, alkenyl of 3 through 10 carbon atoms, alkynyl of 3 through 10 carbon atoms, cycloalkyl of 3 through 12 carbon atoms, cycloalkenyl of 4 through 12 carbon atoms, cycloalkyl alkyl of 4 through 13 carbon atoms, cycloalkenyl alkyl of 5 through 13 carbon atoms, (substituted cycloalkyl)alkyl of 5 through 14 carbon atoms, (substituted cycloalkenyhal
- X is oxygen or sulfur
- n 3, 4, or 5.
- salts of these compounds can also be used accord ing to this invention.
- salts are meant those compounds formed with such cations as sodium, potassium, lithium, calcium, magnesium, barium, strontium, iron, manganese and quaternary ammonium.
- the uracils of Formula 1 also form novel 1:1 addition compounds with excesses of certain nitrogenous bases.
- the exact structure of these compounds is not known. Although the compounds are, generally speaking, poorly soluble in water, they are, according to the best available information, believed to be essentially salt-like in structure. They will be symbolized by the following formula, with the understanding that it is representative only, and is not intended to illustrate actual structure:
- n 3 4, or 5
- NB is a nitrogenous base having an ionization constant K of IO- in water.
- Suitable nitrogeneous bases are substituted, unsubstituted, cyclic and acylic Amines, Amidines, and Guanidines
- the amines can be primary, secondary or tertiary amines, polyamines, arylamines, or heterocyclicarnines. Illustrative of such amines are:
- Ethanolamine Dodecylamine Ethylenediamine Hexamethylenediamine Cocoadiamine Tallowdiamine Hexamethyleneimine Cyclohexylamine Methoxypropylamine Methylamine Dimethylamine Trimethylamine Ethylamine Propylamine Butylamine Octylamine Pyridine Piperidine Tetramethylguanidine Acetamidine Benzylamine Diethylenediamine Z-aminobutanol-l 2-aminooctanol-1 Sec.-butylamine 2-amino-2-methyl-1,3 propanediol Trimethylenediamine Some of the uracils of Formula 1 also form Water stable,
- Z is hydrogen, chlorine, nitro, alkyl of 1 through 3 carbon atoms, bromine or OR (where R, is alkyl of 1 through 3 carbon atoms),
- Y is chlorine or'alkyl of 1 through 3 carbon atoms
- n 3, 4 or 5
- p is /2, 1 or 2.
- This invention is also directed to novel uracils, within the scope of Formula 1.
- uracils are of the formula R is substituted or unsubstituted cycloalkyl radical containing 3 through 10 carbon atoms, a substituted or unsubstituted cycloalkenyl radical containing 4 through 10 carbon atoms, or a B1 CRz a radical, where R is methyl or ethyl, R is an alkyl radical containing 1 through carbon atoms, and R is hydrogen or methyl, and n is 3, 4 or 5.
- substituted alkyl is intended to include such radicals as Bromoalkyl of 1 through carbon atoms, Chloroalkyl of 1 through 10 carbon atoms, Hydroxyalkyl of 1 through 10 carbon atoms, Alkoxyalkyl of 2 through 12 carbon atoms, Alkoxy carbonyl alkyl of 3 through 12 carbon atoms, Dialkyl amino alkyl of 3 through 12 carbon atoms, and Cyanoalkyl of 2 through 10 carbon atoms.
- aryl and substituted aryl embrace radicals such as The terms aralkyl and substituted aralkyl are intended to include such radicals as Furfuryl,
- cycloalkyl, cycloalkenyl, cycloalkyl alkyl, and cycloalkenyl alkyl will incude Cyclopropyl
- cyclic substituents can be further substituted with alkyl groups containing 1 through 4 carbon atoms, methoxy, chlorine and bromine.
- the uracils of Formulae 1 through 4 represent a new class of herbicides offering farmers and property owners a new and effective method for the control of undesirable vegetation.
- uracils exhibit selective action in crops.
- weeds growing in fields of such economic crops as corn, cotton, asparagus, sugar beets, red beets, bobs, spinach, potatoes, peanuts and pineapple can be controlled. This selective activity is described in more detail in the examples Which follow.
- These compounds are also useful for general weed control on industrial sites, railroad rights-of-Way, and areas adjacent to croplands.
- concentrations at which the compounds of this invention are to be used will vary according to the result desired, the type of vegetation, the formulation used, the mode of application, weather conditions, foliage density, and other similar factors. Since so many factors play a role, it is not possible to indicate a concentration suitable for all situations. Generally, when they are used for preemergence treatment in crops, these uracils are used at concentrations of at least about 0.5 pound of active ingredient per acre. Concentrations of from 0.5 to 3 pounds per acre are preferred.
- the uracils When used in non-crop applications, the uracils are used at concentrations of from to 30 pounds of active ingredient per acre. The optimum concentrations to be used in any particular application Will be readily apparent to one skilled in the art.
- R is an alkyl or alkenyl radical containing 3 through 6 carbon atoms, phenyl, substituted phenyl, cycloalkyl radical of 3 through 10 carbon atoms or cycloalkenyl radical of 4 through 10 carbon atoms,
- X is oxygen
- n 3, 4, or 5
- R, X, and n have the same meaning as in Formula 1;
- R is an alkyl radical of 1-6 carbon atoms, H+ is an acid, and B is a base.
- the reaction sequence consists of two steps: first, the acid catalyzed condensation of a l-substituted urea or thiourea with an alkyl 2-cycloalkanone-l-carboxylate to give the ureido intermediate; and, second, the alkaline ring closure of this intermediate to the salt of the uracil product, followed by treatment with acid to liberate the free uracil.
- the first step is best carried out by dissolving or suspending the l-substituted urea or thiourea in a solvent such as xylene, benzene or a 6 mixture of benzene and dioxane, and heating to reflux.
- a solvent such as xylene, benzene or a 6 mixture of benzene and dioxane
- Suitable acid catalysts are phosphoric, poly- 5 phosphoric, formic, chloroacetic, or Lewis acids such as BF ⁇ ; and AlCl
- the mixture is stirred and heated to reflux until the water, split out during the reaction and collected in a suitable apparatus, ceases to be given off.
- the clear solution is decanted or filtered and then con- 10 centrated to give the intermediate ureido derivative.
- the ureido intermediate is dissolved in alcohol containing a slight excess of base, preferably an alkali metal alkoxide or hydroxide, and the solution is refluxed for a short time.
- base preferably an alkali metal alkoxide or hydroxide
- This step effects the ring closure.
- the salt of the uracil is obtained by concentrating this solution to dryness.
- the free uracil is prepared by acidifying an aqueous solution of the salt, and then isolating the solid.
- the salt of the compounds of Formula 1 are prepared by conventional methods such as dissolving the free uracil in an aqueous or nonaqueous solution of at least an equimolar amount of a base or basic salt containing the desired cation.
- a sodium salt can be prepared by dissolving the uracil in water containing an equimolar amount of sodium hydroxide. The salt can then be isolated from the solution by removal of the water.
- the uracil salts which are not soluble in water can be prepared by treating an aqueous solution of an alkali metal salt of the uracil with an aqueous solution of a water-soluble salt of the metal.
- the quaternary ammonium salts of the compounds of Formula 1 are prepared by reacting the substituted uracil with an appropriate quaternary ammonium hydroxide.
- the quaternary ammonium salts of the uracils can be prepared in a dry inert solvent such as toluene or xylene.
- the sodium salt of the uracil is first prepared and appropriate quaternary ammonium halide is then added with stirring and, if necessary, mild heating.
- the sodium halide which forms is removed by filtration, leaving the quaternary ammonium salt of the uracil in solution.
- the solvent-free salt can be prepared by removing the solvent, preferably in vacuo.
- the nitrogenous base-uracil addition compounds of Formula 2 are prepared by mixing an appropriate uracil with a 4 to 20-f0ld weight excess of nitrogenous base. The mixture is heated gently until a clear solution forms.
- addition compounds thus formed are stable in the presence of excess amine and can be diluted with suitable solvents for herbicidal applications.
- the complexes of Formula 3 are formed by co-melting a uracil and a phenol in a 1:2. to 2:1 (uracilzphenol) ratio. They can also be formed by co-dissolving the reactants, in the same ratio, in a nonpolar solvent such as nitromethane or a mixture of nitromethane and cyclohexane.
- the phenol complexes are formed by co-melting, it is not necessary to purify them further for herbicidal uses. If solvents are used in their preparation, they can be isolated by filtration or evaporation of the solvent. The complexes so obtained are also suitable for herbicidal use without further purification.
- HERBICIDAL COMPOSITIONS The uracil compounds described in Formulae 1 through 4 can be prepared for use by incorporating them with adjuvants.
- the amount of herbicide in such preparations can vary 7 over a wide range according to need. Generally speaking, they will contain from about 0.5% to 95%, by weight of a uracil.
- Powder and dust preparations can be made by mixing uracils of the invention with finely-divided solids such as talcs, natural clays, pyrophyllite, diatomaceous earth; flours such as walnut shell, wheat, redwood, soya bean and cotton seed; or inorganic substances such as magnesium carbonate, calcium carbonate, calcium phosphate, sulfur and lime. These preparations are made by thoroughly blending the active ingredient and the solid.
- the particles in such preparations should be less than 50 microns in average diameter, preferably about 20 microns.
- Water-soluble powders can be prepared by blending a suitable uracil with such water-soluble alkaline powders as silicates, carbonates, phosphates or hydroxides, and optionally with water-soluble diluents such as urea or dextrose.
- Granules and pellets can be be made by mixing a finely-divided uracil with a suitable clay such as kaolinite, montmorillonite or attapulgite, moistening this mixture with from 15 to 20% by weight of water, and then extruding the mass through a suitable die under pressure. The extrusions are cut into pro-determined lengths and then dried. These pellets can be granulated if desired.
- a suitable clay such as kaolinite, montmorillonite or attapulgite
- Granules or pellets can also be prepared by spraying a suspension or solution of a uracil onto the surface of a preformed granule of clay, vermiculite or other suitable granular material. If the uracil is in solution, it will penetrate into the pores of the granules and so will adhere without the aid of a binding agent. When the active material is insoluble in the liquid and is carried as a suspension, it is preferable that a binding agent such as goulac, dextrin, swollen starch, glue or polyvinyl alcohol be added. In either case, the granule is then dried and ready for use.
- a binding agent such as goulac, dextrin, swollen starch, glue or polyvinyl alcohol
- the uracils can also be prepared in liquids.
- Water and aliphatic and aromatic hydrocarbons especially those derived from petroleum and having boiling points of from 125 C. to 400 C. are preferred. Hydrocarbons having lower boiling points should not be used because of their undesirable volatilization characteristics and infiammability.
- These liquid preparations are made by dissolving the active in the liquid, or, if the active is insoluble in the liquid, by milling the components in a mill such as a pebble mill until the particles have average diameters of from 1 to 50 microns, preferably 5 to 20 microns.
- the herbicidal preparations can also contain a surface-active agent.
- the surfactant renders the preparations readily dispersible in liquids and improves their action on waxy leaves and the like.
- surface-active agents are used in the preparations at concentrations of from about 1 to 10% by weight.
- surface-active agen is intended to include wetting agents, dispersing agents, suspending agents and emulsifying agents.
- Surface-active agents suitable for use are set forth in Detergents and Emulsifiers upto-date, 1962, John W. McCutcheon, Inc., Morristown, New Jersey. Other surface-active agents which can be used in these preparations are listed in US. Patents 2,139,- 276; 2,412,510; 2,426,417; 2,655,447; and Bulletin E-607 of the Bureau of Entomology and Plant Quarantine of the US. Department of Agriculture.
- the preparations can also contain adhesives, corrosion inhibitors, antifoam agents, dyes and pigments, anticaking agents, and hard water stabilizers.
- the salts of the compounds of Formula 1 are especially advantageous for use as herbicides because many are soluble in water and can be applied as aqueous solutions.
- the compounds of Formula 2 can be formulated as aqueous solutions or as oil-emulsifiable or oil-extendable formulations.
- the nitrogenous base-addition compounds give formulation and application advantages, while still maintaining the desirable herbicidal characteristics of the parent uracils.
- the herbicidal compositions of this invention can be formulated to contain two or more of the uracils. They can also be formulated to contain other known herbicides in addition to the uracils to give compositions which have advantages over the individual components.
- PHENOLS Dinitro-o-sec-butylphenol and its salts Pentachlorophenol and its salts These phenols can be mixed with the uracils in the proportions of 1:10 to 20:1, respectively, the preferred ratio being 1:5 to 5:1.
- N,N-di(n-propyl)thiolcarbarnic acid ethyl ester N,N-di(n-propyl)thiolcarbamic acid, n-propyl ester N-ethyl-N-(n-butyl)thiolcarbamic acid, ethyl ester N-ethyl-N-(n-butyl)thiolcarbamic acid, n-propyl ester Mixed in a 1:2 to 24:1 ratio, preferably a 1:1 to 12:1 ratio.
- B Sodium arsenite Mixed in a 1:10 to 40:1 ratio, preferably a 1:5 to 25:1 ratio.
- G Ammonium sulfamate Mixed in a 1:1 to 100:1 ratio, preferably a 1:1 to 50:1ratio.
- uracils of this invention can be mixed with other substituted uracils, in the respective proportions listed below. Methods for the preparation of the listed uracils can be found in copending applications Serial Nos. 159,746, filed December 15, 1961; 167,434, filed February 1 1 1, 1962; 89,673, filed February 16, 1961; and 89,672, filed February 16, 1961.
- the remaining unrecrystallized solid is dissolved in 2360 parts by Weight of absolute alcohol containing 248 parts by weight of sodium methoxide, and is refluxed for 10 minutes.
- the solvent is stripped at reduced pressure and the residue dissolved in water, cooled, and acidified.
- the solid is filtered 01f, dried, and recrystallized from ethanol to give the desired 3-isopropyl-5,6-trimethyleneuracil, melting at 222223.5 C.
- Example 2 Preparati0n of 3-cycl0hexyl-5,6- trimethyleneuracil
- a mixture of 343 parts by weight of ethyl Z-cyclopentanone-l-carboxyl-ate, 284 parts by weight of cyclohexylurea, 10 parts by weight of p-toluene sulfonic acid, and 1750 parts by weight of xylene is stirred at reflux for 6 hours. During this time the Water given off by the reaction is trapped out. The solvent is stripped from the resulting solution at reduced pressure. The residue is then dissolved in 793 parts by weight of absolute ethyl alcohol.
- Example 3 Preparati0n of 3-allyl-5,6- trimethyleneuracil To a warm stirred slurry of 300 parts by weight of allylurea and 1758 parts by weight of benzene is added a solution of 40 parts by weight .of 100% phosphoric acid in 468 parts by weight of ethyl 2-cyelopentanone-l-carboxylate. The slurry is refluxed for 16 hours during which the water given off .by the reaction is trapped out.
- the resulting solution is decanted and concentrated to an oil.
- a solution of 180 parts by weight of sodium methoxide in 1400 parts by weight of ethyl alcohol is added to this oil and the mixture is refluxed for ten minutes. The solution is then concentrated to dryness and the residue dissolved in 2000 parts by weight of water.
- aqueous basic solution is extracted free of neutral impurities with 1500 parts by weight of ether. It is then cooled and acidified to a pH of 2 with hydrochloric acid. Solid, white 3-allyl-5,-6-trimethyleneuracil, melting at 163.5-166 C., precipitates, which is filtered and dried.
- n-Butylurea 162 3-n-butyl-5,G-trimethylcneuracil.
- n-I-Iexylurea 162 3-n-hexyl-5,(i-trimethyleneuracil.
- Isooctylurea 162 3-iso0ctyl-5 ,fi-trirnethyleneuracil.
- a-Naphthylurea 162 3-(a-naphthyl)-5.6-trimethylene uraei Tcrt-butymrea 116 Ethyl 2 cyelohexanonel-carboxylate... 187 3-tert.-butyl-5,6-tetramethyleneuracil.
- n-Octylurea 172 .dO 187 3-n-octyl-5,6-tetrarnethyleneuracl Cyclooctylurea Methyl 2-cyclopentanone-1-carboxylate.. 156 3-eycloocty1-5,G-trimethylene uracil.
- Cyclopentylurea 128 Ethyl 2-cyclohexanone-l'carboxylate... 187 3-cyclopentyl-5,6-tetramethyleneuracil.
- urac Isopropylurea 102 ...do 162 3-is pr lipyl-5,fi-pentamethyleneuraci n-Amylurea 130 Ethyl 2'cycloheptanone-Lcarboxylate 202 3-n-am yl-5,fi-pentamethylene- 1112101 Bromonorbornylurea 231 ..do 202 3-bromonorb0rnyl-5,6-pentamethyleneuracil. Cyeloheptenylurea 156 do 202 3-cyeloheptenyl-5,6-pentamethyleneuracil. Norbornylurea 152 Methyl 2-cyclopentanone-l-carboxylate.
- denyl)urea methandS-indenyl)-5,6-trimethyleneuraeil. 1 (3a,4,5,6,7,7a-hexahydr0-5-indeny1)-urea- 196 Ethyl 2-cyclohexanone-Lcarboxylate. 187 3-(3a,4,5,6,7,7a-hexahydr0-5-in.
- Example 5 Preparati0n of 3-is0pr0pyl-5,6- trimethyleneuracil, barium salt
- a mixture of 194 parts by weight of 3-isopropyl-5,6- trimethyleneuracil, 600 parts by Weight of methyl alcohol, and 54 parts by Weight of sodium methoxide is stirred until the components are completely dissolved.
- To this mixture is added a solution of 224 parts by weight of barium chloride dihydrate in 1000 parts by Weight of 5 water. The resulting solution is quickly filtered free of foreign matter. A 'White solid gradually separates and is filtered off. This is 3-isopropyl-5,6-trirnethyleneuraoil, barium salt.
- trimethyleneuracil and 865.8 parts of a one-molar solution of tetrabutylammonium hydroxide in methanol is stirred and heated slightly until solution is complete.
- the solvent is removed by distillation under reduced pressure.
- the resulting white solid is essentially pure 3-cy-clohexyl-S,6-trimethyleneuracil, tetrabutylamrnonium salt.
- quaternary ammonium salts can be similarly prepared by reacting equivalent amounts of an appropriately substituted uracil and a suitable quaternary ammonium hydroxide.
- the following compounds can be prepared in this fashion:
- trimethyleneuracil-piperidine addition compound A mixture containing one part of 3-(2-methylcyclohexyl)-5,G-trimethyleneuracil and 20 parts of piperidine is stirred and gently heated until a clear solution is obtained.
- butyl-5,6-tetrametlzyleneuracil with phenol A mixture of 222 parts of 3-sec.-butyl-5,6-tetramethyleneuracil and 94 parts of phenol is gradually heated until a clear melt forms. The liquid is stirred to assure complete mixing and is then allowed to cool.
- Example 10 Preparation of the complex of 3-sec.-butyl- 5,6-tetramethyleneuracil with p-chlorophenol
- a mixture of 222 parts of 3-sec.-butyl-5,G-tetramethyleneuracil and 128 parts of p-chlorophenol is gradually heated until a clear melt forms.
- the liquid is stirred and allowed to cool.
- the resulting solid is recrystallized twice from cyclohexane.
- the resulting white p-chlorophenol complex of 3-sec.butyl-S,fi-tetramethyleneuracil melts at 9193 C.
- Example 12 A queous dispersion The following ingredients (except the water) are mixed, micropulverized, blended with the water and then sand ground until the particles of active material are less than 5 microns in diameter:
- This stable suspension when diluted with water and when applied at the rate of 25 pounds of active ingredient per acre in 100 gallons of water, gives excellent control of such annual weeds as crab grass, foxtail, wild rye, wild barley, bachelor buttons, and lambs-quarters growing in a parking lot.
- Example 13 A qneous suspension The following ingredients are mixed and pebble-milled or sand-milled until substantially all the particles of the active material are under 5 microns in size. The resulting stable thixotropic suspension does not cake on storage and is readily diluted with water to form a very slow settling suspension which requires no agitation during application.
- This suspension when applied as a directed spray at 2 pounds of active ingredient per acre in 30 gallons of water, gives good pre-emergence control of crab grass, mustard species, lambs-quarters, and rice grass germinating in sugar cane.
- Example 14 -A qneous solution Percent 3-sec.-butyl-5,6-tetramethyleneuracil 20 Piperidine 80 The components are mixed together at room temperature until a clear solution is formed. Ths solution is extendable with water.
- the sixty gallons are sprayed on an area of one acre along roadsides. Excellent kill and residual control of such species as wild oats, cheatgrass, annual bluegrass, crab grass, foxtails, ryegrass, filaree, wild mustard, and beggar tick is obtained.
- the mix is wet-milled until all particles are below 10 microns in size.
- the pH of the slurry is then adjusted to about 8.5.
- This formulation gives exceptional control of vegetation around Warehouses and industrial sites. It is dispersed in suflicient water to give good coverage of the area to be sprayed. Applied at the rate of 30 pounds of active ingredients per acre, it gives good control of existing weeds and keeps the area weed-free. Good control of such troublesome weeds as crabgrass, fall panicum, mares tail, goatweed, smartweed, spotted spurge, morning glory, ragweed, pigweed, lambs-quarters, buttonweed, foxtail, broomsedge, and Russian thistle is obtained.
- Example 16 Emulsifiable oil An emulsifiable oil is prepared by mixing the components to give a homogeneous solution. This solution can then be emulsified in water for application.
- This emulsifiable oil is useful for directed postemergence weed control in cotton at lay-by. When applied at 2 pounds of active ingredient per acre in 30 gallons of water, it gives excellent control of germinating annual weeds such as crab grass, cockleburr, and water grass.
- Example Z7.Emulsifiable oil suspension The following components are mixed together and milled in a roller mill, pebble mill, or sand mill until substantially all the particles of the active component are under 10 microns in size. The resulting suspension may be emulsified in Water or diluted further with weed oils for spray application.
- Parafiinic hydrocarbon (at least 90% unsulfonatable) 72.0 Soya lecithin 3.0
- This formulation is dispersed in 80 gallons of diesel oil and sprayed, in a blanket treatment, on vegetation and bare areas along railroad ballast. It is sprayed at a rate of 30 pounds of active ingredients per acre. Good control of Bermuda grass, ragweed, goldenrod, smartweed, seedling Johnson grass, spotted spurge, dogbane, and flower-of-an-hour is obtained.
- Example 20 Oil dispersion Percent 3-sec-butyl-5,6-trimethyleneuracil 20.0 2-(2,4,5-trichlorophenoxy)propionic acid 5.0 Diesel oil 75.0
- This formulation is used for the control of a wide variety of woody and herbaceous perennial weeds and grasses along highway rights-of-way. Dispersed in No. 2 fuel oil, it is sprayed at -20 pounds per acre of active ingredients on dense growths of weeds and brush on highway shoulders. Honeysuckle, brambles, water grass, goldenrod, ragweed, leafy spurge, seedling sassafras, maples, sweet gum, and poison ivy are controlled,
- Example 21 -Oil dispersion Percent 3-cyclohexyl-5,6-tetramethyleneuracil 20.0 2,3,6-trichlorobenzoic acid 10.0 Diesel oil 70.0
- This formulation is dispersed in 100 gallons of herbicidal oil and sprayed along an oil pipeline at the rate of 30 pounds of active ingredients per acre. Excellent control of leafy spurge, bindwced, panic grass, big bluestem, purpletop, poison ivy, quack grass, seedling oaks, maples, sweet gum, ragweed, goldenrod, honeysuckle, and brambles is obtained. The area is kept clear of troublesome weeds for an extended period.
- Example 22 --Oil-extendable formulation Percent 3-sec.-butyl-5,6-tetramethyleneuracil 1 1 complex with phenol 75.0 Soya lecithin 2.6 Calcined montmorillonite clay (Pikes Peak clay) 22.4
- uracil-phenol complexes can be formulated in a like manner, and when used in hcrbicidally equivalent amounts, will give excellent results:
- a wettable powder is prepared with these ingredients by blending and micropulverizing them.
- Example 24 Tank mix A wettable powder is prepared by blending and micropulverizing the following components:
- This wettable powder and an emulsifiable oil containing 6 pounds per gallon of N,N-dipropylthiolcarbamic acid, ethyl ester are added to a spray tank to form a dilute mixture, in water, of to 1%. pounds of uracil formulation and /2 gallon of the ester formulation per gallons.
- This dilute suspension-emulsion is applied at the volume rate of 100 gallons per acre to spring-seeded alfalfa. Good control of such weeds as checkweed, smartweed, portulaca, penny Cress, yellow rocket, shepherds purse, ragweed, redroot pigweed, crab grass, annual bluegrass, and henbit is obtained.
- Example 25 -Tank mix Percent 3-sec.-butyl-5,6-trimethyleneuracil 60.0 Mixed polyoxyethylene esters of fatty acids and oilsoluble petroleum sulfonates 5.0 Attapulgite clay 35.0
- An oil-dispersible powder of these ingredients is prepared by blending and then grinding them to a particle size of less than 50 microns.
- a wettable powder is prepared by blending the components and then micropulverizing them until the particles of the active ingredient are substantially all under 50 microns in size, and then reblending to homogeneity.
- this formulation When applied at 1 pound of active ingredient per acre in 40 gallons of water, this formulation gives excellent pre-emergence control of crab grass, foxtail, cocklebur, lambs quarters, and burdock in a newly planted field of cotton.
- One to three pounds of active ingredient per acre gives good weed control in asparagus, sugar cane, and pineapple.
- One to two pounds per acre gives excellent pre-emergence control annual weeds such as crab grass, foxtail, wild mustard, ryegrass, and velvetleaf in a newly planted field of spinach.
- uracils can be similarly formulated, and when use in herbicidally equivalent amounts, will give good general weed control:
- Example 28 -Wettable powder The following components are blended, then micropulverized until substantially all the solids are under 50 microns in particle size, then reblended to homogeneity:
- Example 29 Wettable powder
- the following powder is prepared in the same manner as Example 28, but in addition is passed through an air 22 attrition m-ill, such as an air-reductionizer, to reduce the particle size to under 10 microns:
- Percent 3-tert.-butyl-5,G-trimethyleneuracil 80.0 Dioctyl sodium sulfosuccinate concreted with sodium benzoate (Aerosol OTB) Partially desulfonated sodium lignin sulfonate Calcined, non-swelling montmorillonite type clay (Pikes Peak clay)
- This composition is used for pre-emergence application in agricultural crops such as sugar cane, asparagus, and safflower. It is dispersed in gallons of water and sprayed with a pressure sprayer. At 0.5 to 2.0 pounds of active ingredient per acre, excellent control of pigweed, lambs-quarters, purslane, mustard, crab grass, foxtail, and water grass is obtained.
- Example 30 Wettable powder The following are blended, then micropnlverized until the particles are below microns in diameter, and reblended:
- Each of the following uracils can be similarly formulated and applied in gallons of herbicidal oil. At rates of 2030 pounds (active) per acre, they will give good Weed control.
- This wettable powder is prepared by blending the components and then micropulverizing the mixture until the particles are under 50 microns in size.
- This formulation is dispersed in water and sprayed preemergence at 5 pounds of active ingredients per acre on a planting of red table beets. Excellent control of crab grass, chickweed, annual morning glory, carpetweed, purslane, smartweed, lambs-quarters, ragweed, black nightshade, giant foxtail, and velvet leaf is obtained. The crop shows no visible injury.
- Example 33 Wettable powder Percent 3-sec.-butyl-5,6-trimethyleneuracil 40.0 3-(4-chlorophenyl)-1,l-dimethylurea 20.0 Alkyl naphthalene sulfonate, Na salt 1.5 Low viscosity methyl cellulose 0.5 Attapulgite clay 38.0
- a wettable powder is prepared by blending these components and then micropulverizing the mixture until the particles are below 50 microns in size.
- This formulation controls weeds along railroad rightsof-way. Applied in the spring in about 100 gallons of water and at the rate of pounds of active ingredients per acre, the formulation gives good control of annual ryegrass, bromegrass, ragweed, henbit, goldenrod, field daisy, buckhorn, plantain, water grass, and volunteer rye.
- Example 34 Wettable powder Percent 3-cyclohexyl-5,6-tetramethyleneuracil 40.0 2-chloro-4-ethylamino-6-isopropyl-amino-s-triazine 20.0
- a wettable powder is prepared by blending these ingredients and then grinding them until the particles are below 50 microns in size.
- a tractor-mounted sprayer which sprays four rows at a time is used to apply this formulation to a field of potatoes, before the potatoes emerge.
- the formulation is used at a rate of 3 pounds of active ingredients per acre.
- Such weeds as crabgrass, chickweed, smartweed, purslane, giant foxtail, annual morning glory, Johnson grass seedlings, barnyard grass, bedstraw, and henbit are controlled without visible injury to the potatoes. Excellent yields of potatoes are obtained, with minimum cultivation.
- Example 35 -Wettable powder Percent 1-(3,4-dichlorophenyl)-3,3-dimethylurea 80.00 Low viscosity methyl cellulose 0.25 Alkyl naphthalene sulfonic acid, sodium salt 1.75 Disodium phosphate 0.80
- Example 36 Pellets Percent 3-cyclohexyl-5,6-tetramethyleneuracil 25 Anhydrous sodium sulfate 10 Sodium lignin sulfonate 10 Ca, Mg bentonite 3-cyclopropyl-5,6-tetramethyleneuracil 3- (chloronorbornyl -5,6-tetramethyleneuracil 3 -cyclopentyl-5 ,6-tetramethyleneuracil 3-r1orbornyl-5,6-tetramethyleneuracil 3-indenyl-5 ,6-tetramethyleneuracil 3-naphthylmethyl-5,6-trimethyleneuracil 3 (p-cumyl -5, 6-trimethyleneuracil 3- (3 ,4,5-trichlorophenyl -5,6-tetramethyleneuracil 3- (4-isopropylcyclohexyl -5 ,6-tetramethyleneu ra cil 3-(de
- trimethyleneuracil Example 37 Pellets Percent 3-cyclohexyl-5,6-trimethyleneuracil 4 3-(p-chlorophenyl)-1,1-dimethylurea 2 Kaolin clay 37 Mississippi sub-bentonite clay 37 Sodium sulfate 10 Sodium lignin sulfonate 10 These ingredients are blended, micropulverized, pugmilled with 17%20% water, and then extruded through -inch die holes. The extrusions are cut into A -inch lengths and dried.
- This formulation controls annual grasses and herbaceous broadleaved weeds in asparagus beds.
- the pellets are distributed evenly over the top of the beds at a rate of 3 pounds of active ingredients per acre just before the cutting season begins and again at the end of the cutting season.
- Excellent control of crabgrass, blackeyed Susan, beggar-ticks, prickly lettuce, ragweed, barnyard grass, green foxtail, pigweed, and fall panicum is obtained.
- Example 38 Percent 3-isopropyl-5,6-trimethyleneuracil 3.33 Phenyldimethylurea 6.67 California sub-bentonite clay 80.00 Sodium sulfate, anhydrous 10.00
- This formulation is used to control all vegetation in a fire lane.
- the pellets are distributed from the air in remote areas of the fire lane at the rate of 40 pounds of active ingredients per acre. Excellent control of elm, sweet gum, oaks, maples, brambles, goldenrod, blackeyed Susan, and honeysuckle is obtained.
- Example 39 Pellets Percent 3-cyclohexyl-5,6-trimethyleneuracil 6.67 3-sec.-butyl-5-chloro-6-methyluracil 3.33 Sodium sulfate, anhydrous 10.00 California sub-bentonite clay 80.00
- This formulation keeps lumber yards free of weeds.
- the pellets are distributed in the spring with a seeder at pounds (actives) per acre.
- the lumber-yard stacking area is kept free of such pernicious weeds as crabgrass, ragweed, pigweed, Russian thistle, fall panicum, goat weed, cheatgrass, and seedling Johnson grass.
- Example 40 -Granules Percent 3-isopropyl-5,6-trimethyleneuracil, Na salt 5 8-15 mesh granular, expanded vermiculite 95
- This granular composition is prepared by dissolving the active material in water and spraying it upon the granules while they are being tumbled. The granules are then dried.
- Granular 8-15 mesh attapulgite clay 96 These granules are applied by hand or by special spreaders at 2.5 pounds of active ingredient per acre for the pre-emergence control of annual weeds in potatoes. They control crabgrass, chickweed, barnyard grass, goose grass, foxtail, velvetleaf, and germinating Johnson grass without visible inujry to the crop.
- Example 42 The following components are blended and micropulverized, then moistened with water and granulated. The granules are then dried and screened.
- Non-swelling sub-bentonite clay 86 The granules are applied with a granule spreader at 3 pounds of active ingredient per acre for pre-emergence control of annular weeds in asparagus.
- potassium salt 5 Preformed attapulgite clay granules, +8 to +15 mesh A granular composition is prepared with these components 'by dissolving the active material in water and spraying it upon the granules while they are being tumbled. The granules are then dried.
- uracil salts can be substituted for the 3- chloronorbornyl-5,6-pentamethyleneuracil, potassium salt. When applied at equivalent rates, good weed control is observed.
- potassium salt 3-isoamyl-5,6-tetramethylene-Z-thiouracil, potassium salt 3-allyl-5,6-pentamethyleneuracil, potassium salt 3-(2-decyl)-5,6-trimethyleneuracil, lithium salt 3-methyl-5,fi-trimethyleneuracil, lithium salt 3-sec.-butyl-5,6-tetramethyleneuracil, lithium salt 27
- the ingredients are blended and micropulverized, then pug-milled with to water, and moist-granulated. After drying, the granules are screened to 8-30 mesh.
- Example 45 Granules Percent 3-isopropyl-5,6-trimethyleneuracil 2.00 Polyoxyethylene tall oil acid ester 0.02
- the surfactant and uracil are first mixed and micropulverized, then suspended in water and sprayed on the remaining granular components While they are being tumbled.
- Example 46 Granules Percent 3-cyclohexyl-5 ,6-trimethyleneuracil 1.0 Trichloroacetic acid, sodium salt 3.0
- Example 47 Waler-s0luble powder Percent 3- Z-methoxyethyl -5 ,6-pentamethyleneuracil Sodium silicate 74 Sodium dioctyl sulfosuccinate 1 These components are blended. and micropulverized.
- a method for the control of undesirable vegetation comprising applying to a locus to be protected from such vegetation a herbicidally effective amount of a compound selected from the group consisting of (a) compounds of the formula 28 where:
- R is selected from the group consisting of alkyl of 1 through 10 carbon atoms, substituted alkyl of 1 through 10 carbon atoms, wherein said substituent is selected from the group consisting of bromine, chlorine, hydroxy, alkoxy, alkoxycarbonyl, dialkylamino, and cyano, aryl of 6 through 14 carbon atoms, substituted aryl of 6 through 14 carbon atoms, wherein said substituent is selected from the group consisting of chlorine, bromine, fluorine, phenyl, alkoxy, alkyl, nitro, trifiuoromethyl, 1,2- tetramethylene, and 1,2-trimethylenylene, aralkyl of 7 through 15 carbon atoms, substituted aralkyl of 7 through 15 carbon atoms, wherein said substituent is selected from the group consisting of chlorine, alkyl, nitro, and alkoxy, tetrahydronaphthylalkyl, alkenyl of 3 through 10 carbon atoms,
- herbicidal active compound is 3-cyclohexyl-5,6-trimethyleneuracil.
- herbicidal active compound is 3-isopropyl-5,6-trimethy1eneuracil.
- herbicidal active compound is 3-sec-butyl-5,6-tetramethyleneuracil.
- herbicidal active compound is 3-cyclohexyl-5,6-tetramethyleneuracil.
- herbicidal active compound is 3-isopropyl-5,6-trimethyleneuracil, sodium salt.
- herbicidal active compound is 3-cyclohexyl-5,6-trimethyleneuracil potassium salt.
- a method for the control of undesirable vegetation comprising applying to a locus to be protected from such vegetation a herbicidally effective amount of a compound selected from the group consisting of (a) compounds of the formula it i where R is selected from the group consisting of alkyl of 1 through 10 carbon atoms,
- substituted alkyl of 1 through 10 carbon atoms wherein said substituent is selected from the group consisting of bromine, chlorine, hydroxy, alkoxy, alkoxycarbonyl, dialkylamino, and cyano,
- substituted aryl of 6 through 14 carbon atoms wherein said substituent is selected from the group consisting of chlorine, bromine, fluorine, phenyl, alkoxy, alkyl, nitro, trifluoromethyl, 1,2- tetramethylene, and 1,2-trimethylenylene,
- substituted aralkyl of 7 through 15 carbon atoms wherein said substituent is selected from the group consisting of chlorine, alkyl, nitro, and alkoxy,
- substituted cycloalkyl of 3 through 12 carbon atoms wherein said substituent is selected from the group consisting of bromine, chlorine, methoxy, and alkyl,
- substituted cycloalkenyl of 4 through 12 carbon atoms wherein said substituent is selected from the group consisting of bromine, chlorine, methoxy, and alkyl,
- X is selected from the group consisting of oxygen and sulfur; and n is a number 3 through 5;
- R and n are as defined above, and 15 NB is a nitrogenous base having an ionization constant K l0 in water; and (d) compounds of the formula H o Z 0 ll RN @ECHDD H O ⁇ N p 111-1 where R and n are as defined above, Z is selected from the group consisting of hydrogen,
- R is an alkyl of 1 through 3 carbon atoms
- Y is selected from the group consisting of chlorine and alkyl of 1 through 3 carbon atoms; in is a number 1 through 5; and
- p is selected from the group consisting of /2, 1 and 2.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
Priority Applications (40)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DK106253D DK106253A (no) | 1959-08-14 | ||
IT635567D IT635567A (no) | 1959-08-14 | ||
BE594076D BE594076A (no) | 1959-08-14 | ||
CA731651A CA731651A (en) | 1959-08-14 | Substituted uracils | |
NL254838D NL254838A (no) | 1959-08-14 | ||
SE7792/60A SE305770B (no) | 1959-08-14 | 1960-08-12 | |
DE19601240698 DE1240698C2 (de) | 1959-08-14 | 1960-08-12 | Unkrautbekaempfungsmittel |
CH921360A CH482402A (de) | 1959-08-14 | 1960-08-13 | Unkrautbekämpfungsmittel |
GB17419/64A GB968665A (en) | 1959-08-14 | 1960-08-15 | 3-substituted uracils |
GB28141/60A GB968661A (en) | 1959-08-14 | 1960-08-15 | Herbicidal compositions containing 3-substituted uracils |
GB17417/64A GB968663A (en) | 1959-08-14 | 1960-08-15 | 3-substituted uracils |
GB17418/64A GB968664A (en) | 1959-08-14 | 1960-08-15 | 3-substituted uracils |
FR835959A FR1270771A (fr) | 1959-08-14 | 1960-08-16 | Nouveaux uraciles substitués et leur préparation |
US217521A US3235357A (en) | 1959-08-14 | 1962-08-17 | Method for the control of undesirable vegetation |
US232311A US3235360A (en) | 1959-08-14 | 1962-10-22 | Control of undesirable vegetation |
GB619566A GB1035096A (en) | 1959-08-14 | 1962-12-07 | Improvements relating to herbicides |
GB619366A GB1035094A (en) | 1959-08-14 | 1962-12-07 | Improvements relating to herbicides and novel 3-substituted uracils |
GB619166A GB1035092A (en) | 1959-08-14 | 1962-12-07 | Improvements relating to herbicides and novel 3-substituted uracils |
GB619466A GB1035095A (en) | 1959-08-14 | 1962-12-07 | Improvements relating to herbicides and novel 3-substituted uracils |
NO14675262A NO117095B (no) | 1959-08-14 | 1962-12-10 | |
DK534662A DK113254B (da) | 1959-08-14 | 1962-12-10 | Herbicid. |
SE13294/62A SE350496B (no) | 1959-08-14 | 1962-12-10 | |
CH923666A CH490008A (de) | 1959-08-14 | 1962-12-11 | Unkrautbekämpfungsmittel |
CH923466A CH489201A (de) | 1959-08-14 | 1962-12-11 | Unkrautbekämpfungsmittel |
CH923566A CH490007A (de) | 1959-08-14 | 1962-12-11 | Unkrautbekämpfungsmittel |
CH1449962A CH487591A (de) | 1959-08-14 | 1962-12-11 | Unkrautbekämpfungsmittel |
BR14539162A BR6245391D0 (pt) | 1959-08-14 | 1962-12-11 | Composicoes herbicidas |
US284835A US3254082A (en) | 1959-08-14 | 1963-06-03 | Process for preparing substituted uracils |
OA51234A OA01145A (fr) | 1961-12-11 | 1964-12-30 | Uraciles substitués, compositions herbicides en contenant, leur préparation et leur utilisation. |
DK185565A DK129315B (da) | 1959-08-14 | 1965-04-12 | Herbicid. |
BR171453/65A BR6571453D0 (pt) | 1959-08-14 | 1965-07-20 | Composicoes herbicidas e processo para preparar ingredientes ativos das mesmas |
BR17145265A BR6571452D0 (pt) | 1959-08-14 | 1965-07-20 | Composicoes herbicidas e processo de preparar complexos de uracila fenol usaveis como ingredientes ativos das mesma |
US516686A US3360521A (en) | 1959-08-14 | 1965-12-27 | 3-substituted-5, 6-alkyleneuracils |
MY1965102A MY6500102A (en) | 1959-08-14 | 1965-12-31 | Herbicidal compositions containing 3- substituted uracils |
MY1965115A MY6500115A (en) | 1959-08-14 | 1965-12-31 | 3- substituted uracils |
MY1965103A MY6500103A (en) | 1959-08-14 | 1965-12-31 | 3- substituted uracils |
MY1965116A MY6500116A (en) | 1959-08-14 | 1965-12-31 | 3- substituted uracils |
MY6900393A MY6900393A (en) | 1959-08-14 | 1969-12-31 | Improvements relating to herbicides and novel-3-substituted uracils |
MY6900392A MY6900392A (en) | 1959-08-14 | 1969-12-31 | Improvements relating to herbicides and novel3-substituted uracils |
MY6900391A MY6900391A (en) | 1959-08-14 | 1969-12-31 | Improvements relating to herbicides |
Applications Claiming Priority (15)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US83370559A | 1959-08-14 | 1959-08-14 | |
US83370459A | 1959-08-14 | 1959-08-14 | |
US1295960A | 1960-03-07 | 1960-03-07 | |
US1295760A | 1960-03-07 | 1960-03-07 | |
US1295660A | 1960-03-07 | 1960-03-07 | |
US1296860A | 1960-03-07 | 1960-03-07 | |
US1295860A | 1960-03-07 | 1960-03-07 | |
US1296760A | 1960-03-07 | 1960-03-07 | |
US4883760A | 1960-08-11 | 1960-08-11 | |
US8498061A | 1961-01-26 | 1961-01-26 | |
US8967461A | 1961-02-16 | 1961-02-16 | |
US12363661A | 1961-07-13 | 1961-07-13 | |
US15974661A | 1961-12-15 | 1961-12-15 | |
US232311A US3235360A (en) | 1959-08-14 | 1962-10-22 | Control of undesirable vegetation |
US284835A US3254082A (en) | 1959-08-14 | 1963-06-03 | Process for preparing substituted uracils |
Publications (1)
Publication Number | Publication Date |
---|---|
US3235360A true US3235360A (en) | 1966-02-15 |
Family
ID=27585449
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US232311A Expired - Lifetime US3235360A (en) | 1959-08-14 | 1962-10-22 | Control of undesirable vegetation |
US284835A Expired - Lifetime US3254082A (en) | 1959-08-14 | 1963-06-03 | Process for preparing substituted uracils |
Family Applications After (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US284835A Expired - Lifetime US3254082A (en) | 1959-08-14 | 1963-06-03 | Process for preparing substituted uracils |
Country Status (12)
Country | Link |
---|---|
US (2) | US3235360A (no) |
BE (1) | BE594076A (no) |
BR (1) | BR6571453D0 (no) |
CA (1) | CA731651A (no) |
CH (1) | CH482402A (no) |
DE (1) | DE1240698C2 (no) |
DK (1) | DK106253A (no) |
GB (2) | GB968661A (no) |
IT (1) | IT635567A (no) |
MY (4) | MY6500115A (no) |
NL (1) | NL254838A (no) |
SE (1) | SE305770B (no) |
Cited By (23)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3330640A (en) * | 1964-05-27 | 1967-07-11 | Du Pont | Method for the control of undesirable vegetation |
US3436207A (en) * | 1965-02-23 | 1969-04-01 | Du Pont | Control of undesirable vegetation |
US3462435A (en) * | 1966-11-15 | 1969-08-19 | United States Borax Chem | Alkyleneiminoquinazoline-2,4-diones |
US3464989A (en) * | 1967-05-19 | 1969-09-02 | United States Borax Chem | 3-alkyleneiminoquinazoline-4-imino-2-ones |
US3471282A (en) * | 1968-07-12 | 1969-10-07 | Du Pont | Herbicidal compositions containing poly uracils |
US3532699A (en) * | 1968-07-12 | 1970-10-06 | Du Pont | Herbicidal poly uracils |
US3539333A (en) * | 1968-08-21 | 1970-11-10 | Gulf Research Development Co | Combating weeds in sugar beets |
US3869275A (en) * | 1970-12-04 | 1975-03-04 | Schering Ag | Herbicidal mixtures |
US3931171A (en) * | 1970-02-05 | 1976-01-06 | Bayer Aktiengesellschaft | Process for the production of 2,3-dihydro-1,3-oxazinedione-(2,4)-compounds |
US4111681A (en) * | 1976-09-09 | 1978-09-05 | E. I. Du Pont De Nemours And Company | Cycloalkanapyrazole-3-carbonitrile herbicides |
FR2498894A1 (fr) * | 1981-02-04 | 1982-08-06 | Lecalvez Robert | Desherbant selectif a base de lenacile et de neburon |
US4859229A (en) * | 1986-07-31 | 1989-08-22 | Hoffmann-La Roche Inc. | 3-Aryluracils having an ether (thio) carbomyloxy or sulphomyloxy substituent on the aromatic moiety |
US5017211A (en) * | 1987-09-23 | 1991-05-21 | Ciba-Geigy Corporation | Heterocyclic compounds |
US5183492A (en) * | 1989-06-29 | 1993-02-02 | Ciba-Geigy Corporation | Herbicidal 3-aryluracils |
US5310723A (en) * | 1993-08-05 | 1994-05-10 | Fmc Corporation | Herbicidal 3-(1-substituted-quinolin-2-on-7-yl)-1-substituted-6-trifluoromethyluracils |
US5391541A (en) * | 1993-08-11 | 1995-02-21 | Fmc Corporation | Herbicidal 3-(substituted-benzyl)-1-methyl-6-trifluoromethyluracils |
US6409988B1 (en) | 1999-07-01 | 2002-06-25 | 3-Dimensional Pharmaceuticals, Inc. | Radiolabeled 1-aryl pyrazoles, the synthesis thereof and the use thereof as pest GABA receptor ligands |
US6506784B1 (en) | 1999-07-01 | 2003-01-14 | 3-Dimensional Pharmaceuticals, Inc. | Use of 1,3-substituted pyrazol-5-yl sulfonates as pesticides |
US6518266B1 (en) | 1999-07-22 | 2003-02-11 | 3-Dimensional Pharmaceuticals | 1- Aryl-3-thioalkyl pyrazoles, the synthesis thereof and the use thereof as insecticides |
US6545033B1 (en) | 1999-10-06 | 2003-04-08 | 3-Dimensional Pharmaceuticals, Inc. | Fused 1-(2,6-dichloro-4-trifluoromethylphenyl)-pyrazoles, the synthesis thereof and the use thereof as pesticides |
EP2052608A1 (de) | 2007-10-24 | 2009-04-29 | Bayer CropScience AG | Herbizid-Kombination |
EP2090166A1 (de) | 2008-02-14 | 2009-08-19 | Bayer CropScience AG | Flüssige herbizide Zubereitungen |
DE102008037631A1 (de) | 2008-08-14 | 2010-02-18 | Bayer Cropscience Ag | Herbizid-Kombination mit Dimethoxytriazinyl-substituierten Difluormethansulfonylaniliden |
Families Citing this family (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
NL272286A (no) * | 1960-12-27 | |||
GB1384506A (en) * | 1972-03-24 | 1975-02-19 | American Cyanamid Co | 2,3,5-substituted-6-trifluoromethyl-1,3-diazin-4-ones |
US4189366A (en) * | 1979-01-15 | 1980-02-19 | Eastman Kodak Company | Radiation curable compositions containing 5-halo-6-halomethyluracil derivatives as photoinitiators |
EP0260621A3 (de) * | 1986-09-18 | 1989-03-15 | F. HOFFMANN-LA ROCHE & CO. Aktiengesellschaft | 3-Aryluracil-enoläther und deren Verwendung zur Unkrautbekämpfung |
US5149810A (en) * | 1988-04-22 | 1992-09-22 | Imperial Chemical Industries Plc | Pyrimidine compounds |
EP0338686B1 (en) * | 1988-04-22 | 1994-06-22 | Zeneca Limited | Pyrimidinone derivatives |
DE58908208D1 (de) * | 1988-07-29 | 1994-09-22 | Ciba Geigy Ag | Thiouracile als Stabilisatoren für chlorhaltige Polymerisate. |
GB8908638D0 (en) * | 1989-04-17 | 1989-06-01 | Ici Plc | Novel compounds |
US6344460B1 (en) | 1999-03-19 | 2002-02-05 | Lonza Inc. | Propynyl uracils |
CN114656408B (zh) * | 2022-04-12 | 2024-09-06 | 药源药物化学(上海)有限公司 | 一种植物保护剂中间体的合成工艺 |
Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2567651A (en) * | 1951-09-11 | J-dialkyl-g-amino-l | ||
US2688020A (en) * | 1952-01-17 | 1954-08-31 | American Cyanamid Co | Preparation of dihydrouracils |
US2969364A (en) * | 1957-12-26 | 1961-01-24 | Upjohn Co | Derivatives of 5-amino uracil |
US3002975A (en) * | 1958-08-25 | 1961-10-03 | Diamond Alkali Co | Process for the preparation of 1,3-dihalo-uracils |
US3078154A (en) * | 1956-11-07 | 1963-02-19 | Geigy Ag J R | Method for inhibiting the growth of plants |
US3086854A (en) * | 1959-02-05 | 1963-04-23 | Du Pont | Method for the control of plant growth |
Family Cites Families (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2444024A (en) * | 1948-06-29 | Sydney archer | ||
US2937175A (en) * | 1960-05-17 | Preparation of orotic acid | ||
US2899435A (en) * | 1959-08-11 | S-neopentyl s-aixyl barbituric acid | ||
GB693912A (en) * | 1949-04-01 | 1953-07-08 | Us Rubber Co | Plant growth regulants and phytocides |
US2820035A (en) * | 1953-10-07 | 1958-01-14 | Boehringer Sohn Ingelheim | Barbituric acid derivatives |
BE553585A (no) * | 1955-12-21 | |||
NL100471C (no) * | 1956-04-04 |
-
0
- NL NL254838D patent/NL254838A/xx unknown
- BE BE594076D patent/BE594076A/xx unknown
- CA CA731651A patent/CA731651A/en not_active Expired
- DK DK106253D patent/DK106253A/da unknown
- IT IT635567D patent/IT635567A/it unknown
-
1960
- 1960-08-12 SE SE7792/60A patent/SE305770B/xx unknown
- 1960-08-12 DE DE19601240698 patent/DE1240698C2/de not_active Expired
- 1960-08-13 CH CH921360A patent/CH482402A/de not_active IP Right Cessation
- 1960-08-15 GB GB28141/60A patent/GB968661A/en not_active Expired
- 1960-08-15 GB GB17417/64A patent/GB968663A/en not_active Expired
-
1962
- 1962-10-22 US US232311A patent/US3235360A/en not_active Expired - Lifetime
-
1963
- 1963-06-03 US US284835A patent/US3254082A/en not_active Expired - Lifetime
-
1965
- 1965-07-20 BR BR171453/65A patent/BR6571453D0/pt unknown
- 1965-12-31 MY MY1965115A patent/MY6500115A/xx unknown
- 1965-12-31 MY MY1965116A patent/MY6500116A/xx unknown
- 1965-12-31 MY MY1965102A patent/MY6500102A/xx unknown
- 1965-12-31 MY MY1965103A patent/MY6500103A/xx unknown
Patent Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2567651A (en) * | 1951-09-11 | J-dialkyl-g-amino-l | ||
US2688020A (en) * | 1952-01-17 | 1954-08-31 | American Cyanamid Co | Preparation of dihydrouracils |
US3078154A (en) * | 1956-11-07 | 1963-02-19 | Geigy Ag J R | Method for inhibiting the growth of plants |
US2969364A (en) * | 1957-12-26 | 1961-01-24 | Upjohn Co | Derivatives of 5-amino uracil |
US3002975A (en) * | 1958-08-25 | 1961-10-03 | Diamond Alkali Co | Process for the preparation of 1,3-dihalo-uracils |
US3086854A (en) * | 1959-02-05 | 1963-04-23 | Du Pont | Method for the control of plant growth |
Cited By (24)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3330640A (en) * | 1964-05-27 | 1967-07-11 | Du Pont | Method for the control of undesirable vegetation |
US3436207A (en) * | 1965-02-23 | 1969-04-01 | Du Pont | Control of undesirable vegetation |
US3462435A (en) * | 1966-11-15 | 1969-08-19 | United States Borax Chem | Alkyleneiminoquinazoline-2,4-diones |
US3464989A (en) * | 1967-05-19 | 1969-09-02 | United States Borax Chem | 3-alkyleneiminoquinazoline-4-imino-2-ones |
US3471282A (en) * | 1968-07-12 | 1969-10-07 | Du Pont | Herbicidal compositions containing poly uracils |
US3532699A (en) * | 1968-07-12 | 1970-10-06 | Du Pont | Herbicidal poly uracils |
US3539333A (en) * | 1968-08-21 | 1970-11-10 | Gulf Research Development Co | Combating weeds in sugar beets |
US3931171A (en) * | 1970-02-05 | 1976-01-06 | Bayer Aktiengesellschaft | Process for the production of 2,3-dihydro-1,3-oxazinedione-(2,4)-compounds |
US3869275A (en) * | 1970-12-04 | 1975-03-04 | Schering Ag | Herbicidal mixtures |
US4111681A (en) * | 1976-09-09 | 1978-09-05 | E. I. Du Pont De Nemours And Company | Cycloalkanapyrazole-3-carbonitrile herbicides |
FR2498894A1 (fr) * | 1981-02-04 | 1982-08-06 | Lecalvez Robert | Desherbant selectif a base de lenacile et de neburon |
US4859229A (en) * | 1986-07-31 | 1989-08-22 | Hoffmann-La Roche Inc. | 3-Aryluracils having an ether (thio) carbomyloxy or sulphomyloxy substituent on the aromatic moiety |
US5017211A (en) * | 1987-09-23 | 1991-05-21 | Ciba-Geigy Corporation | Heterocyclic compounds |
US5183492A (en) * | 1989-06-29 | 1993-02-02 | Ciba-Geigy Corporation | Herbicidal 3-aryluracils |
US5310723A (en) * | 1993-08-05 | 1994-05-10 | Fmc Corporation | Herbicidal 3-(1-substituted-quinolin-2-on-7-yl)-1-substituted-6-trifluoromethyluracils |
US5391541A (en) * | 1993-08-11 | 1995-02-21 | Fmc Corporation | Herbicidal 3-(substituted-benzyl)-1-methyl-6-trifluoromethyluracils |
US6409988B1 (en) | 1999-07-01 | 2002-06-25 | 3-Dimensional Pharmaceuticals, Inc. | Radiolabeled 1-aryl pyrazoles, the synthesis thereof and the use thereof as pest GABA receptor ligands |
US6506784B1 (en) | 1999-07-01 | 2003-01-14 | 3-Dimensional Pharmaceuticals, Inc. | Use of 1,3-substituted pyrazol-5-yl sulfonates as pesticides |
US6518266B1 (en) | 1999-07-22 | 2003-02-11 | 3-Dimensional Pharmaceuticals | 1- Aryl-3-thioalkyl pyrazoles, the synthesis thereof and the use thereof as insecticides |
US6545033B1 (en) | 1999-10-06 | 2003-04-08 | 3-Dimensional Pharmaceuticals, Inc. | Fused 1-(2,6-dichloro-4-trifluoromethylphenyl)-pyrazoles, the synthesis thereof and the use thereof as pesticides |
EP2052608A1 (de) | 2007-10-24 | 2009-04-29 | Bayer CropScience AG | Herbizid-Kombination |
EP2090166A1 (de) | 2008-02-14 | 2009-08-19 | Bayer CropScience AG | Flüssige herbizide Zubereitungen |
DE102008037631A1 (de) | 2008-08-14 | 2010-02-18 | Bayer Cropscience Ag | Herbizid-Kombination mit Dimethoxytriazinyl-substituierten Difluormethansulfonylaniliden |
US20100062941A1 (en) * | 2008-08-14 | 2010-03-11 | Bayer Cropscience Ag | Herbicide Combination Comprising Dimethoxytriazinyl-Substituted Difluoromethanesulfonylanilides |
Also Published As
Publication number | Publication date |
---|---|
MY6500116A (en) | 1965-12-31 |
MY6500102A (en) | 1965-12-31 |
DK106253A (no) | 1900-01-01 |
DE1240698B (no) | 1973-01-04 |
SE305770B (no) | 1968-11-04 |
NL254838A (no) | 1900-01-01 |
GB968661A (en) | 1964-09-02 |
GB968663A (en) | 1964-09-02 |
CH482402A (de) | 1969-12-15 |
BR6571453D0 (pt) | 1973-05-10 |
CA731651A (en) | 1966-04-05 |
US3254082A (en) | 1966-05-31 |
DE1240698C2 (de) | 1973-01-04 |
BE594076A (no) | 1900-01-01 |
MY6500103A (en) | 1965-12-31 |
IT635567A (no) | 1900-01-01 |
MY6500115A (en) | 1965-12-31 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
US3235360A (en) | Control of undesirable vegetation | |
US3235361A (en) | Method for the control of undesirable vegetation | |
US3235357A (en) | Method for the control of undesirable vegetation | |
EP0104532B1 (en) | O-halobenzoic acid derivatives, process for their preparation, herbicidal compositions and their use | |
US3235363A (en) | Method for the control of undesirable vegetation | |
US3235358A (en) | Control of undesirable vegetation | |
US3322526A (en) | Herbicidal composition and method | |
US3360521A (en) | 3-substituted-5, 6-alkyleneuracils | |
CA1291761C (en) | Certain substituted 4-benzoyl-3,5-dioxotetrahydropyrans and thiopyrans | |
US3374083A (en) | Method for the control of undesirable vegetation with 3, 5, 6-substituted uracils | |
US3436207A (en) | Control of undesirable vegetation | |
US3497515A (en) | 3,5,6-substituted uracils | |
US3189431A (en) | Method for the control of undesirable plant growth | |
US4160037A (en) | Compounds, compositions and methods of combatting pest employing thioureas | |
US3235362A (en) | Method for the control of weeds | |
US3352863A (en) | 3, 5-disubstituted uracils | |
US3244503A (en) | Methods for the control of plants | |
US3803148A (en) | Isoxazolopyrimidine herbicides and method of controlling plant growth | |
US3988300A (en) | Benzophenone ureas and method for utilizing the same | |
IL32113A (en) | 1-alkoxycarbonyl uracils,their preparation and herbicidal compositions containing them | |
US3216816A (en) | Herbicidal composition and method | |
US3360522A (en) | 3-bicycloalkyl-6-methyluracil | |
US3388153A (en) | 3-phenyl-3-hydroxyureas and thioureas | |
US3089765A (en) | Herbicidal method | |
US3512955A (en) | Method of protecting plant growth |