IL32113A - 1-alkoxycarbonyl uracils,their preparation and herbicidal compositions containing them - Google Patents

1-alkoxycarbonyl uracils,their preparation and herbicidal compositions containing them

Info

Publication number: IL32113A
Authority: IL; Israel
Prior art keywords: carbon atoms; formula; alkyl; methyluracil; uracil
Prior art date: 1968-05-13

Application number

IL32113A

Other languages

English (en)

Other versions

IL32113A0 (en

Original Assignee

Du Pont

Priority date (The priority date 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 date listed.)

1968-05-13

Filing date

1969-04-30

Publication date

1973-10-25

1969-04-30 Application filed by Du Pont filed Critical Du Pont

1969-06-25 Publication of IL32113A0 publication Critical patent/IL32113A0/xx

1973-10-25 Publication of IL32113A publication Critical patent/IL32113A/en

Links

239000000203 mixture Substances 0.000 title claims description 34
238000002360 preparation method Methods 0.000 title claims description 19
230000002363 herbicidal effect Effects 0.000 title claims description 9
ISAKRJDGNUQOIC-UHFFFAOYSA-N Uracil Chemical group O=C1C=CNC(=O)N1 ISAKRJDGNUQOIC-UHFFFAOYSA-N 0.000 claims description 74
-1 methoxy, ethoxy Chemical group 0.000 claims description 68
125000004432 carbon atom Chemical group C* 0.000 claims description 66
229940035893 uracil Drugs 0.000 claims description 37
150000001875 compounds Chemical class 0.000 claims description 33
125000000217 alkyl group Chemical group 0.000 claims description 21
239000000460 chlorine Substances 0.000 claims description 15
229910052801 chlorine Inorganic materials 0.000 claims description 15
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 12
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 10
229910052794 bromium Inorganic materials 0.000 claims description 10
239000004009 herbicide Substances 0.000 claims description 9
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 8
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims description 8
125000003545 alkoxy group Chemical group 0.000 claims description 8
125000003118 aryl group Chemical group 0.000 claims description 8
239000001257 hydrogen Substances 0.000 claims description 8
229910052739 hydrogen Inorganic materials 0.000 claims description 8
238000002156 mixing Methods 0.000 claims description 8
239000012312 sodium hydride Substances 0.000 claims description 8
229910000104 sodium hydride Inorganic materials 0.000 claims description 8
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 7
125000001309 chloro group Chemical group Cl* 0.000 claims description 7
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 6
229910052731 fluorine Inorganic materials 0.000 claims description 6
239000011737 fluorine Substances 0.000 claims description 6
239000011734 sodium Substances 0.000 claims description 6
229910052708 sodium Inorganic materials 0.000 claims description 6
125000003710 aryl alkyl group Chemical group 0.000 claims description 5
125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 5
125000000753 cycloalkyl group Chemical group 0.000 claims description 5
238000000034 method Methods 0.000 claims description 5
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
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 claims description 4
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
239000003960 organic solvent Substances 0.000 claims description 4
150000002989 phenols Chemical class 0.000 claims description 4
125000004076 pyridyl group Chemical group 0.000 claims description 4
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
125000003342 alkenyl group Chemical group 0.000 claims description 3
125000000304 alkynyl group Chemical group 0.000 claims description 3
125000001246 bromo group Chemical group Br* 0.000 claims description 3
125000000392 cycloalkenyl group Chemical group 0.000 claims description 3
239000011593 sulfur Chemical group 0.000 claims description 3
229910052717 sulfur Chemical group 0.000 claims description 3
125000004849 alkoxymethyl group Chemical group 0.000 claims description 2
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 claims description 2
125000004093 cyano group Chemical group *C#N 0.000 claims description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
125000001153 fluoro group Chemical group F* 0.000 claims description 2
125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims description 2
125000002541 furyl group Chemical group 0.000 claims description 2
229910052736 halogen Inorganic materials 0.000 claims description 2
150000002367 halogens Chemical class 0.000 claims description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
125000002768 hydroxyalkyl group Chemical group 0.000 claims description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
239000001301 oxygen Substances 0.000 claims description 2
229910052760 oxygen Inorganic materials 0.000 claims description 2
125000000547 substituted alkyl group Chemical group 0.000 claims description 2
125000001544 thienyl group Chemical group 0.000 claims description 2
125000004429 atom Chemical group 0.000 claims 2
150000002431 hydrogen Chemical class 0.000 claims 2
238000004519 manufacturing process Methods 0.000 claims 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
125000005055 alkyl alkoxy group Chemical group 0.000 claims 1
229910052799 carbon Inorganic materials 0.000 claims 1
150000003839 salts Chemical class 0.000 description 32
241000196324 Embryophyta Species 0.000 description 19
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
239000002904 solvent Substances 0.000 description 17
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
244000025670 Eleusine indica Species 0.000 description 14
235000014716 Eleusine indica Nutrition 0.000 description 14
239000000243 solution Substances 0.000 description 14
239000000376 reactant Substances 0.000 description 13
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
239000008187 granular material Substances 0.000 description 12
239000004480 active ingredient Substances 0.000 description 11
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 10
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 10
239000002253 acid Substances 0.000 description 10
239000003921 oil Substances 0.000 description 10
235000001602 Digitaria X umfolozi Nutrition 0.000 description 9
235000017898 Digitaria ciliaris Nutrition 0.000 description 9
235000005476 Digitaria cruciata Nutrition 0.000 description 9
235000006830 Digitaria didactyla Nutrition 0.000 description 9
235000005804 Digitaria eriantha ssp. eriantha Nutrition 0.000 description 9
235000010823 Digitaria sanguinalis Nutrition 0.000 description 9
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
239000007787 solid Substances 0.000 description 9
239000002245 particle Substances 0.000 description 8
239000004094 surface-active agent Substances 0.000 description 8
239000000725 suspension Substances 0.000 description 8
244000281762 Chenopodium ambrosioides Species 0.000 description 7
239000004615 ingredient Substances 0.000 description 7
235000003129 Ambrosia artemisiifolia var elatior Nutrition 0.000 description 6
239000002202 Polyethylene glycol Substances 0.000 description 6
235000003484 annual ragweed Nutrition 0.000 description 6
235000006263 bur ragweed Nutrition 0.000 description 6
235000003488 common ragweed Nutrition 0.000 description 6
150000002148 esters Chemical class 0.000 description 6
239000007788 liquid Substances 0.000 description 6
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
239000008188 pellet Substances 0.000 description 6
229920001223 polyethylene glycol Polymers 0.000 description 6
239000000047 product Substances 0.000 description 6
235000009736 ragweed Nutrition 0.000 description 6
238000010992 reflux Methods 0.000 description 6
125000001424 substituent group Chemical group 0.000 description 6
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
235000014820 Galium aparine Nutrition 0.000 description 5
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
229960000892 attapulgite Drugs 0.000 description 5
239000004927 clay Substances 0.000 description 5
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 5
239000000706 filtrate Substances 0.000 description 5
229910052943 magnesium sulfate Inorganic materials 0.000 description 5
235000019341 magnesium sulphate Nutrition 0.000 description 5
229910052625 palygorskite Inorganic materials 0.000 description 5
238000003756 stirring Methods 0.000 description 5
240000006122 Chenopodium album Species 0.000 description 4
235000009344 Chenopodium album Nutrition 0.000 description 4
244000058871 Echinochloa crus-galli Species 0.000 description 4
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
238000001816 cooling Methods 0.000 description 4
239000004495 emulsifiable concentrate Substances 0.000 description 4
238000001704 evaporation Methods 0.000 description 4
230000008020 evaporation Effects 0.000 description 4
238000001914 filtration Methods 0.000 description 4
238000009472 formulation Methods 0.000 description 4
239000000463 material Substances 0.000 description 4
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
239000000126 substance Substances 0.000 description 4
244000105624 Arachis hypogaea Species 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 3
235000003222 Helianthus annuus Nutrition 0.000 description 3
235000009198 Lamium amplexicaule Nutrition 0.000 description 3
244000303225 Lamium amplexicaule Species 0.000 description 3
239000002879 Lewis base Substances 0.000 description 3
235000004431 Linum usitatissimum Nutrition 0.000 description 3
240000006240 Linum usitatissimum Species 0.000 description 3
240000002439 Sorghum halepense Species 0.000 description 3
240000006694 Stellaria media Species 0.000 description 3
NBQCNZYJJMBDKY-UHFFFAOYSA-N Terbacil Chemical compound CC=1NC(=O)N(C(C)(C)C)C(=O)C=1Cl NBQCNZYJJMBDKY-UHFFFAOYSA-N 0.000 description 3
240000008042 Zea mays Species 0.000 description 3
235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 3
235000002017 Zea mays subsp mays Nutrition 0.000 description 3
150000007513 acids Chemical class 0.000 description 3
235000013877 carbamide Nutrition 0.000 description 3
238000006243 chemical reaction Methods 0.000 description 3
AOGYCOYQMAVAFD-UHFFFAOYSA-N chlorocarbonic acid Chemical class OC(Cl)=O AOGYCOYQMAVAFD-UHFFFAOYSA-N 0.000 description 3
235000005822 corn Nutrition 0.000 description 3
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 3
239000003085 diluting agent Substances 0.000 description 3
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 3
239000007789 gas Substances 0.000 description 3
125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
150000007527 lewis bases Chemical class 0.000 description 3
XMJHPCRAQCTCFT-UHFFFAOYSA-N methyl chloroformate Chemical compound COC(Cl)=O XMJHPCRAQCTCFT-UHFFFAOYSA-N 0.000 description 3
235000020232 peanut Nutrition 0.000 description 3
239000000843 powder Substances 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 3
UVMTZTPUIFOAGM-UHFFFAOYSA-N (3-chlorophenyl)carbamic acid Chemical compound OC(=O)NC1=CC=CC(Cl)=C1 UVMTZTPUIFOAGM-UHFFFAOYSA-N 0.000 description 2
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 2
244000198134 Agave sisalana Species 0.000 description 2
241000803625 Andropogon virginicus Species 0.000 description 2
244000003416 Asparagus officinalis Species 0.000 description 2
235000005340 Asparagus officinalis Nutrition 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
244000056139 Brassica cretica Species 0.000 description 2
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-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
241000207199 Citrus Species 0.000 description 2
244000052363 Cynodon dactylon Species 0.000 description 2
244000000626 Daucus carota Species 0.000 description 2
241000508725 Elymus repens Species 0.000 description 2
BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 2
241000208818 Helianthus Species 0.000 description 2
239000002841 Lewis acid Substances 0.000 description 2
240000004658 Medicago sativa Species 0.000 description 2
235000017587 Medicago sativa ssp. sativa Nutrition 0.000 description 2
235000012629 Mentha aquatica Nutrition 0.000 description 2
244000246386 Mentha pulegium Species 0.000 description 2
235000016257 Mentha pulegium Nutrition 0.000 description 2
235000004357 Mentha x piperita Nutrition 0.000 description 2
241000219925 Oenothera Species 0.000 description 2
240000000275 Persicaria hydropiper Species 0.000 description 2
235000017337 Persicaria hydropiper Nutrition 0.000 description 2
235000004442 Polygonum persicaria Nutrition 0.000 description 2
240000000111 Saccharum officinarum Species 0.000 description 2
235000007201 Saccharum officinarum Nutrition 0.000 description 2
235000005187 Taraxacum officinale ssp. officinale Nutrition 0.000 description 2
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
239000002585 base Substances 0.000 description 2
239000011230 binding agent Substances 0.000 description 2
238000009835 boiling Methods 0.000 description 2
239000011575 calcium Substances 0.000 description 2
229910052791 calcium Inorganic materials 0.000 description 2
RYAGRZNBULDMBW-UHFFFAOYSA-L calcium;3-(2-hydroxy-3-methoxyphenyl)-2-[2-methoxy-4-(3-sulfonatopropyl)phenoxy]propane-1-sulfonate Chemical compound [Ca+2].COC1=CC=CC(CC(CS([O-])(=O)=O)OC=2C(=CC(CCCS([O-])(=O)=O)=CC=2)OC)=C1O RYAGRZNBULDMBW-UHFFFAOYSA-L 0.000 description 2
150000001735 carboxylic acids Chemical class 0.000 description 2
239000003153 chemical reaction reagent Substances 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
235000020971 citrus fruits Nutrition 0.000 description 2
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
235000019329 dioctyl sodium sulphosuccinate Nutrition 0.000 description 2
239000006185 dispersion Substances 0.000 description 2
239000000428 dust Substances 0.000 description 2
230000000694 effects Effects 0.000 description 2
239000003995 emulsifying agent Substances 0.000 description 2
239000000839 emulsion Substances 0.000 description 2
RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 2
235000001050 hortel pimenta Nutrition 0.000 description 2
229930195733 hydrocarbon Natural products 0.000 description 2
150000002430 hydrocarbons Chemical class 0.000 description 2
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
230000007774 longterm Effects 0.000 description 2
XBCXJKGHPABGSD-UHFFFAOYSA-N methyluracil Natural products CN1C=CC(=O)NC1=O XBCXJKGHPABGSD-UHFFFAOYSA-N 0.000 description 2
PSZYNBSKGUBXEH-UHFFFAOYSA-M naphthalene-1-sulfonate Chemical compound C1=CC=C2C(S(=O)(=O)[O-])=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-M 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 2
239000012053 oil suspension Substances 0.000 description 2
239000012044 organic layer Substances 0.000 description 2
IZUPBVBPLAPZRR-UHFFFAOYSA-N pentachlorophenol Chemical compound OC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl IZUPBVBPLAPZRR-UHFFFAOYSA-N 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
239000000377 silicon dioxide Substances 0.000 description 2
239000007858 starting material Substances 0.000 description 2
235000012222 talc Nutrition 0.000 description 2
RWQNBRDOKXIBIV-UHFFFAOYSA-N thymine Chemical compound CC1=CNC(=O)NC1=O RWQNBRDOKXIBIV-UHFFFAOYSA-N 0.000 description 2
150000003918 triazines Chemical class 0.000 description 2
150000003672 ureas Chemical class 0.000 description 2
238000005406 washing Methods 0.000 description 2
DTGKSKDOIYIVQL-WEDXCCLWSA-N (+)-borneol Chemical group C1C[C@@]2(C)[C@@H](O)C[C@@H]1C2(C)C DTGKSKDOIYIVQL-WEDXCCLWSA-N 0.000 description 1
JIHQDMXYYFUGFV-UHFFFAOYSA-N 1,3,5-triazine Chemical compound C1=NC=NC=N1 JIHQDMXYYFUGFV-UHFFFAOYSA-N 0.000 description 1
KMRSAYURVOHHGF-UHFFFAOYSA-N 1-acetyl-5-bromo-6-methyl-3-propan-2-ylpyrimidine-2,4-dione 5-chloro-6-methyl-3-propan-2-yl-1-(trichloromethylsulfanyl)pyrimidine-2,4-dione Chemical compound C(C)(C)N1C(N(C(=C(C1=O)Cl)C)SC(Cl)(Cl)Cl)=O.C(C)(C)N1C(N(C(=C(C1=O)Br)C)C(C)=O)=O KMRSAYURVOHHGF-UHFFFAOYSA-N 0.000 description 1
YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-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
RQAPBIOXXSQHEU-UHFFFAOYSA-N 2,3-dichloro-6-methylbenzoic acid Chemical compound CC1=CC=C(Cl)C(Cl)=C1C(O)=O RQAPBIOXXSQHEU-UHFFFAOYSA-N 0.000 description 1
AUAXYMOBWXOEQD-UHFFFAOYSA-N 2,5-dichloro-3-nitrobenzoic acid Chemical compound OC(=O)C1=CC(Cl)=CC([N+]([O-])=O)=C1Cl AUAXYMOBWXOEQD-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
LLWADFLAOKUBDR-UHFFFAOYSA-N 2-methyl-4-chlorophenoxybutyric acid Chemical compound CC1=CC(Cl)=CC=C1OCCCC(O)=O LLWADFLAOKUBDR-UHFFFAOYSA-N 0.000 description 1
BZSXEZOLBIJVQK-UHFFFAOYSA-N 2-methylsulfonylbenzoic acid Chemical compound CS(=O)(=O)C1=CC=CC=C1C(O)=O BZSXEZOLBIJVQK-UHFFFAOYSA-N 0.000 description 1
XENORHLEQQVHAP-UHFFFAOYSA-N 3-(3,4-dichlorophenyl)-1,1-diethylurea Chemical compound CCN(CC)C(=O)NC1=CC=C(Cl)C(Cl)=C1 XENORHLEQQVHAP-UHFFFAOYSA-N 0.000 description 1
WOGWFRIFWLMPMS-UHFFFAOYSA-N 3-benzyl-5-chloro-6-methyl-1h-pyrimidine-2,4-dione Chemical compound O=C1C(Cl)=C(C)NC(=O)N1CC1=CC=CC=C1 WOGWFRIFWLMPMS-UHFFFAOYSA-N 0.000 description 1
WMTDYEHRRKBVPY-UHFFFAOYSA-N 3-propyl-1h-pyrimidine-2,4-dione Chemical compound CCCN1C(=O)C=CNC1=O WMTDYEHRRKBVPY-UHFFFAOYSA-N 0.000 description 1
UATTVYPRSYQMDN-UHFFFAOYSA-N 5-(chloromethyl)-6-methyl-1h-pyrimidine-2,4-dione Chemical compound CC=1NC(=O)NC(=O)C=1CCl UATTVYPRSYQMDN-UHFFFAOYSA-N 0.000 description 1
AKPATAVUEYOGRE-UHFFFAOYSA-N 5-bromo-3,6-dimethyl-1h-pyrimidine-2,4-dione Chemical compound CC=1NC(=O)N(C)C(=O)C=1Br AKPATAVUEYOGRE-UHFFFAOYSA-N 0.000 description 1
CTSLUCNDVMMDHG-UHFFFAOYSA-N 5-bromo-3-(butan-2-yl)-6-methylpyrimidine-2,4(1H,3H)-dione Chemical compound CCC(C)N1C(=O)NC(C)=C(Br)C1=O CTSLUCNDVMMDHG-UHFFFAOYSA-N 0.000 description 1
HEAXNUZNYDEXFG-UHFFFAOYSA-N 5-bromo-6-methyl-1h-pyrimidine-2,4-dione Chemical compound CC=1NC(=O)NC(=O)C=1Br HEAXNUZNYDEXFG-UHFFFAOYSA-N 0.000 description 1
NDPPNZKDAFBRBT-UHFFFAOYSA-N 5-chloro-3-cyclohexyl-1h-pyrimidine-2,4-dione Chemical compound O=C1C(Cl)=CNC(=O)N1C1CCCCC1 NDPPNZKDAFBRBT-UHFFFAOYSA-N 0.000 description 1
SHVCSCWHWMSGTE-UHFFFAOYSA-N 6-methyluracil Chemical compound CC1=CC(=O)NC(=O)N1 SHVCSCWHWMSGTE-UHFFFAOYSA-N 0.000 description 1
240000005020 Acaciella glauca Species 0.000 description 1
MDBGGTQNNUOQRC-UHFFFAOYSA-N Allidochlor Chemical compound ClCC(=O)N(CC=C)CC=C MDBGGTQNNUOQRC-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
244000099147 Ananas comosus Species 0.000 description 1
235000007119 Ananas comosus Nutrition 0.000 description 1
235000007320 Avena fatua Nutrition 0.000 description 1
244000075850 Avena orientalis Species 0.000 description 1
241001645380 Bassia scoparia Species 0.000 description 1
BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 1
SZPGJVFAWSTYDZ-UHFFFAOYSA-N BrC=1C(N(C(NC1C)=O)C(C)C)=O.N1C(=O)NC(=O)C=C1 Chemical compound BrC=1C(N(C(NC1C)=O)C(C)C)=O.N1C(=O)NC(=O)C=C1 SZPGJVFAWSTYDZ-UHFFFAOYSA-N 0.000 description 1
235000011331 Brassica Nutrition 0.000 description 1
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235000008733 Citrus aurantifolia Nutrition 0.000 description 1
NZJFTUQPIOAZPB-UHFFFAOYSA-N ClC1=CC=C(C=C1)NC(N(C)C)=O.ClC=1C=C(C=CC1Cl)NC(N(C)C)=O Chemical compound ClC1=CC=C(C=C1)NC(N(C)C)=O.ClC=1C=C(C=CC1Cl)NC(N(C)C)=O NZJFTUQPIOAZPB-UHFFFAOYSA-N 0.000 description 1
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239000004375 Dextrin Substances 0.000 description 1
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244000068988 Glycine max Species 0.000 description 1
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240000001549 Ipomoea eriocarpa Species 0.000 description 1
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240000007049 Juglans regia Species 0.000 description 1
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239000005909 Kieselgur Substances 0.000 description 1
241000209082 Lolium 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
LKJPSUCKSLORMF-UHFFFAOYSA-N Monolinuron Chemical compound CON(C)C(=O)NC1=CC=C(Cl)C=C1 LKJPSUCKSLORMF-UHFFFAOYSA-N 0.000 description 1
235000003805 Musa ABB Group Nutrition 0.000 description 1
240000005561 Musa balbisiana Species 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
235000004496 Oenothera biennis Nutrition 0.000 description 1
229910019142 PO4 Inorganic materials 0.000 description 1
235000011999 Panicum crusgalli Nutrition 0.000 description 1
241001148659 Panicum dichotomiflorum Species 0.000 description 1
241001478756 Panicum sp. Species 0.000 description 1
235000010503 Plantago lanceolata Nutrition 0.000 description 1
244000239204 Plantago lanceolata Species 0.000 description 1
235000015266 Plantago major Nutrition 0.000 description 1
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QOSMNYMQXIVWKY-UHFFFAOYSA-N Propyl levulinate Chemical compound CCCOC(=O)CCC(C)=O QOSMNYMQXIVWKY-UHFFFAOYSA-N 0.000 description 1
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235000017016 Setaria faberi Nutrition 0.000 description 1
241000820191 Setaria magna Species 0.000 description 1
241000607059 Solidago Species 0.000 description 1
244000197975 Solidago virgaurea Species 0.000 description 1
235000000914 Solidago virgaurea Nutrition 0.000 description 1
235000011684 Sorghum saccharatum Nutrition 0.000 description 1
244000062793 Sorghum vulgare Species 0.000 description 1
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235000011941 Tilia x europaea Nutrition 0.000 description 1
WHKUVVPPKQRRBV-UHFFFAOYSA-N Trasan Chemical compound CC1=CC(Cl)=CC=C1OCC(O)=O WHKUVVPPKQRRBV-UHFFFAOYSA-N 0.000 description 1
235000021307 Triticum Nutrition 0.000 description 1
244000098338 Triticum aestivum Species 0.000 description 1
235000005373 Uvularia sessilifolia Nutrition 0.000 description 1
PWFKZPQQQKLWEA-UHFFFAOYSA-N [Br-].[Br-].[NH+]1=CC=NC=C1.[NH+]1=CC=NC=C1 Chemical compound [Br-].[Br-].[NH+]1=CC=NC=C1.[NH+]1=CC=NC=C1 PWFKZPQQQKLWEA-UHFFFAOYSA-N 0.000 description 1
239000011149 active material Substances 0.000 description 1
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230000001070 adhesive effect Effects 0.000 description 1
239000002671 adjuvant Substances 0.000 description 1
238000013019 agitation Methods 0.000 description 1
150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
125000006307 alkoxy benzyl group Chemical group 0.000 description 1
125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
125000002877 alkyl aryl group Chemical group 0.000 description 1
150000004996 alkyl benzenes Chemical class 0.000 description 1
125000005037 alkyl phenyl group Chemical group 0.000 description 1
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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
150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
PXWUKZGIHQRDHL-UHFFFAOYSA-N atraton Chemical compound CCNC1=NC(NC(C)C)=NC(OC)=N1 PXWUKZGIHQRDHL-UHFFFAOYSA-N 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
239000004305 biphenyl Substances 0.000 description 1
235000005770 birds nest Nutrition 0.000 description 1
QKSKPIVNLNLAAV-UHFFFAOYSA-N bis(2-chloroethyl) sulfide Chemical compound ClCCSCCCl QKSKPIVNLNLAAV-UHFFFAOYSA-N 0.000 description 1
229910021538 borax Inorganic materials 0.000 description 1
125000005997 bromomethyl group Chemical group 0.000 description 1
229940103357 calcium arsenate Drugs 0.000 description 1
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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
239000004202 carbamide Substances 0.000 description 1
150000004649 carbonic acid derivatives Chemical class 0.000 description 1
FZFAMSAMCHXGEF-UHFFFAOYSA-N chloro formate Chemical compound ClOC=O FZFAMSAMCHXGEF-UHFFFAOYSA-N 0.000 description 1
125000004965 chloroalkyl group Chemical group 0.000 description 1
244000237902 common dandelion Species 0.000 description 1
239000012141 concentrate Substances 0.000 description 1
230000007797 corrosion Effects 0.000 description 1
238000005260 corrosion Methods 0.000 description 1
239000013078 crystal Substances 0.000 description 1
125000004122 cyclic group Chemical group 0.000 description 1
125000001047 cyclobutenyl group Chemical group C1(=CCC1)* 0.000 description 1
239000002274 desiccant Substances 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
IWEDIXLBFLAXBO-UHFFFAOYSA-N dicamba Chemical compound COC1=C(Cl)C=CC(Cl)=C1C(O)=O IWEDIXLBFLAXBO-UHFFFAOYSA-N 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-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
238000001035 drying Methods 0.000 description 1
239000000975 dye Substances 0.000 description 1
BLQUEYLSBBYPKM-UHFFFAOYSA-N ethyl 3-chlorothiophene-2-carboxylate Chemical compound CCOC(=O)C=1SC=CC=1Cl BLQUEYLSBBYPKM-UHFFFAOYSA-N 0.000 description 1
125000004494 ethyl ester group Chemical group 0.000 description 1
125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 description 1
239000000284 extract Substances 0.000 description 1
238000000605 extraction Methods 0.000 description 1
238000001125 extrusion Methods 0.000 description 1
235000013312 flour Nutrition 0.000 description 1
125000003709 fluoroalkyl group Chemical group 0.000 description 1
239000000295 fuel oil Substances 0.000 description 1
239000003292 glue Substances 0.000 description 1
239000008233 hard water Substances 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
239000012456 homogeneous solution Substances 0.000 description 1
150000004679 hydroxides Chemical class 0.000 description 1
125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 1
239000003112 inhibitor Substances 0.000 description 1
NRXQIUSYPAHGNM-UHFFFAOYSA-N ioxynil Chemical compound OC1=C(I)C=C(C#N)C=C1I NRXQIUSYPAHGNM-UHFFFAOYSA-N 0.000 description 1
238000002955 isolation Methods 0.000 description 1
229910052622 kaolinite Inorganic materials 0.000 description 1
CYPPCCJJKNISFK-UHFFFAOYSA-J kaolinite Chemical compound [OH-].[OH-].[OH-].[OH-].[Al+3].[Al+3].[O-][Si](=O)O[Si]([O-])=O CYPPCCJJKNISFK-UHFFFAOYSA-J 0.000 description 1
230000002045 lasting effect Effects 0.000 description 1
238000002386 leaching Methods 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
ZTMKADLOSYKWCA-UHFFFAOYSA-N lenacil Chemical compound O=C1NC=2CCCC=2C(=O)N1C1CCCCC1 ZTMKADLOSYKWCA-UHFFFAOYSA-N 0.000 description 1
239000004571 lime 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
238000002844 melting Methods 0.000 description 1
125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
ZNGQMTWDRPJJRU-UHFFFAOYSA-N methyl 5-bromo-3-butan-2-yl-6-methyl-2,4-dioxopyrimidine-1-carboxylate Chemical compound COC(=O)N1C(=O)N(C(=O)C(=C1C)Br)C(C)CC ZNGQMTWDRPJJRU-UHFFFAOYSA-N 0.000 description 1
UCFFGYASXIPWPD-UHFFFAOYSA-N methyl hypochlorite Chemical compound COCl UCFFGYASXIPWPD-UHFFFAOYSA-N 0.000 description 1
JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 description 1
238000003801 milling Methods 0.000 description 1
229910052901 montmorillonite Inorganic materials 0.000 description 1
235000010460 mustard Nutrition 0.000 description 1
125000004433 nitrogen atom Chemical group N* 0.000 description 1
125000004365 octenyl group Chemical group C(=CCCCCCC)* 0.000 description 1
UZGLIIJVICEWHF-UHFFFAOYSA-N octogen Chemical compound [O-][N+](=O)N1CN([N+]([O-])=O)CN([N+]([O-])=O)CN([N+]([O-])=O)C1 UZGLIIJVICEWHF-UHFFFAOYSA-N 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
239000004533 oil dispersion Substances 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
ILUJQPXNXACGAN-UHFFFAOYSA-N ortho-methoxybenzoic acid Natural products COC1=CC=CC=C1C(O)=O ILUJQPXNXACGAN-UHFFFAOYSA-N 0.000 description 1
239000003208 petroleum Substances 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
229920002451 polyvinyl alcohol Polymers 0.000 description 1
239000011148 porous material Substances 0.000 description 1
CAEWJEXPFKNBQL-UHFFFAOYSA-N prop-2-enyl carbonochloridate Chemical compound ClC(=O)OCC=C CAEWJEXPFKNBQL-UHFFFAOYSA-N 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
238000000746 purification Methods 0.000 description 1
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
235000003499 redwood Nutrition 0.000 description 1
150000004760 silicates Chemical class 0.000 description 1
PTLRDCMBXHILCL-UHFFFAOYSA-M sodium arsenite Chemical compound [Na+].[O-][As]=O PTLRDCMBXHILCL-UHFFFAOYSA-M 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
229940056729 sodium sulfate anhydrous Drugs 0.000 description 1
239000004328 sodium tetraborate Substances 0.000 description 1
235000010339 sodium tetraborate Nutrition 0.000 description 1
HCJLVWUMMKIQIM-UHFFFAOYSA-M sodium;2,3,4,5,6-pentachlorophenolate Chemical compound [Na+].[O-]C1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl HCJLVWUMMKIQIM-UHFFFAOYSA-M 0.000 description 1
239000007921 spray Substances 0.000 description 1
238000005507 spraying Methods 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000008107 starch Substances 0.000 description 1
125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
235000001508 sulfur Nutrition 0.000 description 1
239000000375 suspending agent Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 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
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
238000001665 trituration Methods 0.000 description 1
239000010455 vermiculite Substances 0.000 description 1
229910052902 vermiculite Inorganic materials 0.000 description 1
235000019354 vermiculite Nutrition 0.000 description 1
235000020234 walnut Nutrition 0.000 description 1
238000010792 warming Methods 0.000 description 1
239000004563 wettable powder Substances 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1
235000005765 wild carrot Nutrition 0.000 description 1
239000008096 xylene 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
- C07D239/24—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
- C07D239/60—Three or more oxygen or sulfur 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

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Plural Heterocyclic Compounds (AREA)

IL32113A 1968-05-13 1969-04-30 1-alkoxycarbonyl uracils,their preparation and herbicidal compositions containing them IL32113A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US72879568A	1968-05-13	1968-05-13

Publications (2)

Publication Number	Publication Date
IL32113A0 IL32113A0 (en)	1969-06-25
IL32113A true IL32113A (en)	1973-10-25

Family

ID=24928307

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IL32113A IL32113A (en)	1968-05-13	1969-04-30	1-alkoxycarbonyl uracils,their preparation and herbicidal compositions containing them

Country Status (6)

Country	Link
JP (1)	JPS4831898B1 (fr)
DE (1)	DE1924232A1 (fr)
FR (1)	FR2008386A1 (fr)
GB (1)	GB1257259A (fr)
IL (1)	IL32113A (fr)
OA (1)	OA03321A (fr)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE1283665B (de) *	1966-02-03	1968-11-21	Interelectric Ag	Karte fuer Glueckwunsch- und Visitenzwecke und Verfahren zu ihrer Herstellung
JPS5633918U (fr) *	1979-08-21	1981-04-02
FR2549060B1 (fr) *	1983-07-11	1986-06-27	Roussel Uclaf	Nouveaux uraciles substitues comportant en position 1 un groupement phenyloxy substitue, leur procede de preparation et les compositions herbicides les renfermant
DK167280B1 (da) *	1985-03-20	1993-10-04	Ciba Geigy Ag	3-aryluracilderivater, fremgangsmaade til fremstilling deraf, ukrudtsbekaempelsesmidler indeholdende disse derivater samt anvendelsen af derivaterne til ukrudtsbekaempelse
DK366887A (da) *	1986-07-31	1988-05-13	Hoffmann La Roche	Pyrimidinderivater
BR8807217A (pt) *	1987-09-23	1989-10-17	Hoffmann La Roche	Compostos heterocilicos
EP0436680B1 (fr) *	1989-06-29	1994-09-07	Ciba-Geigy Ag	Composes heterocycliques

1969
- 1969-04-30 IL IL32113A patent/IL32113A/en unknown
- 1969-05-10 OA OA53604A patent/OA03321A/fr unknown
- 1969-05-12 DE DE19691924232 patent/DE1924232A1/de active Pending
- 1969-05-12 FR FR6915301A patent/FR2008386A1/fr not_active Withdrawn
- 1969-05-12 JP JP44035802A patent/JPS4831898B1/ja active Pending
- 1969-05-13 GB GB1257259D patent/GB1257259A/en not_active Expired

Also Published As

Publication number	Publication date
GB1257259A (fr)	1971-12-15
JPS4831898B1 (fr)	1973-10-02
IL32113A0 (en)	1969-06-25
OA03321A (fr)	1970-12-15
FR2008386A1 (fr)	1970-01-23
DE1924232A1 (de)	1969-11-27

Publication	Publication Date	Title
US3235361A (en)	1966-02-15	Method for the control of undesirable vegetation
US3235357A (en)	1966-02-15	Method for the control of undesirable vegetation
EP0195346B1 (fr)	1992-06-24	3-Aryluraciles et leur utilisation comme herbicides
US3235360A (en)	1966-02-15	Control of undesirable vegetation
EP0625970B1 (fr)	1997-09-17	Herbicides contenant des sulfonamides
US4551531A (en)	1985-11-05	4-Difluoromethoxy-2-amino-pyrimidines
CA1094067A (fr)	1981-01-20	Sulfonamides a proprietes herbicides
US4545811A (en)	1985-10-08	N-Phenylsulfonyl-N'-triazinyl-ureas
US5053072A (en)	1991-10-01	Heterocyclic n-acylsulfonamides, and their use as herbicides or growth regulators
US3235363A (en)	1966-02-15	Method for the control of undesirable vegetation
US4478635A (en)	1984-10-23	N-Arylsulfonyl-N'-pyrimidinylureas
US4927451A (en)	1990-05-22	3-aryldihydrouracils
EP0338465B1 (fr)	1993-06-02	1-Chloropyrimidinyl-1H-1,2,4-triazole-3-sulfonamides, procédé pour leur préparation et leur utilisation comme agent à activité herbicide
US3235358A (en)	1966-02-15	Control of undesirable vegetation
EP0244166A2 (fr)	1987-11-04	Sulfonamides acétyl hétérocycliques
US4301286A (en)	1981-11-17	Herbicidal O-alkyl sulfonylisoureas
US3322526A (en)	1967-05-30	Herbicidal composition and method
US3933815A (en)	1976-01-20	Trifluoromethyl triazines
US5462914A (en)	1995-10-31	Herbicidal n-cyanopyridazinones
US3436207A (en)	1969-04-01	Control of undesirable vegetation
US3959331A (en)	1976-05-25	Allophanimidate herbicides
DD284799A5 (de)	1990-11-28	Herbizide zusammensetzung und verfahren zur bekaempfung von unkraeutern
US3352662A (en)	1967-11-14	Method of inhibiting growth of undesired vegetation
US3360521A (en)	1967-12-26	3-substituted-5, 6-alkyleneuracils
US3235362A (en)	1966-02-15	Method for the control of weeds