CA1076588A - Acyclic, alicyclic and aromatic n-substituted halo-substituted 2-pyrrolidinones and their utility as herbicides - Google Patents
Acyclic, alicyclic and aromatic n-substituted halo-substituted 2-pyrrolidinones and their utility as herbicidesInfo
- Publication number
- CA1076588A CA1076588A CA248,947A CA248947A CA1076588A CA 1076588 A CA1076588 A CA 1076588A CA 248947 A CA248947 A CA 248947A CA 1076588 A CA1076588 A CA 1076588A
- Authority
- CA
- Canada
- Prior art keywords
- chlorine
- hydrogen
- bromine
- trifluoromethyl
- compound according
- 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
Links
- 125000002015 acyclic group Chemical group 0.000 title claims abstract description 10
- 125000002723 alicyclic group Chemical group 0.000 title claims abstract description 10
- 239000004009 herbicide Substances 0.000 title abstract description 10
- 125000003118 aryl group Chemical group 0.000 title description 2
- 150000003953 γ-lactams Chemical class 0.000 title 1
- 239000000460 chlorine Chemical group 0.000 claims abstract description 213
- 229910052801 chlorine Chemical group 0.000 claims abstract description 169
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims abstract description 109
- 239000001257 hydrogen Substances 0.000 claims abstract description 106
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 106
- 150000001875 compounds Chemical class 0.000 claims abstract description 97
- 125000001309 chloro group Chemical group Cl* 0.000 claims abstract description 65
- 238000000034 method Methods 0.000 claims abstract description 61
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims abstract description 54
- 229910052794 bromium Chemical group 0.000 claims abstract description 54
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims abstract description 51
- -1 trifluoromethylthio, trifluoromethyl-sulfinyl Chemical group 0.000 claims abstract description 49
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 44
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 26
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 26
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 25
- 239000001301 oxygen Substances 0.000 claims abstract description 25
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 24
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 24
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical group [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 18
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 17
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 13
- 239000011737 fluorine Chemical group 0.000 claims abstract description 13
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 13
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims abstract description 12
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims abstract description 12
- 125000004414 alkyl thio group Chemical group 0.000 claims abstract description 12
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 12
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims abstract description 11
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims abstract description 11
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 11
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 11
- 125000001188 haloalkyl group Chemical group 0.000 claims abstract description 11
- 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 claims abstract description 11
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims abstract description 9
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 9
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims abstract description 9
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 7
- 229910052717 sulfur Chemical group 0.000 claims abstract description 7
- 239000011593 sulfur Chemical group 0.000 claims abstract description 7
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims abstract description 6
- 125000004803 chlorobenzyl group Chemical group 0.000 claims abstract 9
- 238000006243 chemical reaction Methods 0.000 claims description 27
- CWYNVVGOOAEACU-UHFFFAOYSA-N Fe2+ Chemical compound [Fe+2] CWYNVVGOOAEACU-UHFFFAOYSA-N 0.000 claims description 22
- 239000002904 solvent Substances 0.000 claims description 21
- 229960002089 ferrous chloride Drugs 0.000 claims description 18
- NMCUIPGRVMDVDB-UHFFFAOYSA-L iron dichloride Chemical group Cl[Fe]Cl NMCUIPGRVMDVDB-UHFFFAOYSA-L 0.000 claims description 18
- 229910001448 ferrous ion Inorganic materials 0.000 claims description 15
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 claims description 14
- 230000003197 catalytic effect Effects 0.000 claims description 9
- 229910021575 Iron(II) bromide Inorganic materials 0.000 claims description 8
- GYCHYNMREWYSKH-UHFFFAOYSA-L iron(ii) bromide Chemical compound [Fe+2].[Br-].[Br-] GYCHYNMREWYSKH-UHFFFAOYSA-L 0.000 claims description 8
- 238000006462 rearrangement reaction Methods 0.000 claims description 8
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 7
- 239000003054 catalyst Substances 0.000 claims description 7
- 229940046149 ferrous bromide Drugs 0.000 claims description 7
- 238000011084 recovery Methods 0.000 claims description 7
- 238000009835 boiling Methods 0.000 claims description 6
- KTWOOEGAPBSYNW-UHFFFAOYSA-N ferrocene Chemical compound [Fe+2].C=1C=C[CH-]C=1.C=1C=C[CH-]C=1 KTWOOEGAPBSYNW-UHFFFAOYSA-N 0.000 claims description 6
- 125000001246 bromo group Chemical group Br* 0.000 claims description 4
- 230000012010 growth Effects 0.000 claims description 4
- 125000002950 monocyclic group Chemical group 0.000 claims description 2
- 150000002431 hydrogen Chemical group 0.000 claims 65
- BWLBGMIXKSTLSX-UHFFFAOYSA-N 2-hydroxyisobutyric acid Chemical compound CC(C)(O)C(O)=O BWLBGMIXKSTLSX-UHFFFAOYSA-N 0.000 claims 4
- 125000001539 acetonyl group Chemical group [H]C([H])([H])C(=O)C([H])([H])* 0.000 claims 4
- DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical compound NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-N 0.000 claims 3
- 229910052740 iodine Inorganic materials 0.000 claims 2
- 239000011630 iodine Substances 0.000 claims 2
- 125000005034 trifluormethylthio group Chemical group FC(S*)(F)F 0.000 claims 1
- 239000000203 mixture Substances 0.000 description 44
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 33
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 28
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 24
- 239000000047 product Substances 0.000 description 24
- 238000002360 preparation method Methods 0.000 description 20
- 238000010992 reflux Methods 0.000 description 17
- 241000196324 Embryophyta Species 0.000 description 16
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 16
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- 239000002689 soil Substances 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 239000007788 liquid Substances 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 244000152970 Digitaria sanguinalis Species 0.000 description 8
- 235000010823 Digitaria sanguinalis Nutrition 0.000 description 8
- 239000003921 oil Substances 0.000 description 8
- 239000007921 spray Substances 0.000 description 8
- 125000004432 carbon atom Chemical group C* 0.000 description 7
- 239000000543 intermediate Substances 0.000 description 7
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 7
- 235000019341 magnesium sulphate Nutrition 0.000 description 7
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 7
- FKHIFSZMMVMEQY-UHFFFAOYSA-N talc Chemical compound [Mg+2].[O-][Si]([O-])=O FKHIFSZMMVMEQY-UHFFFAOYSA-N 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- 239000012299 nitrogen atmosphere Substances 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 244000075850 Avena orientalis Species 0.000 description 5
- 235000001602 Digitaria X umfolozi Nutrition 0.000 description 5
- 235000017898 Digitaria ciliaris Nutrition 0.000 description 5
- 235000005476 Digitaria cruciata Nutrition 0.000 description 5
- 235000006830 Digitaria didactyla Nutrition 0.000 description 5
- 235000005804 Digitaria eriantha ssp. eriantha Nutrition 0.000 description 5
- 235000014716 Eleusine indica Nutrition 0.000 description 5
- 239000003153 chemical reaction reagent Substances 0.000 description 5
- WCGGWVOVFQNRRS-UHFFFAOYSA-N dichloro-acetic acid amide Natural products NC(=O)C(Cl)Cl WCGGWVOVFQNRRS-UHFFFAOYSA-N 0.000 description 5
- 230000002363 herbicidal effect Effects 0.000 description 5
- 231100000208 phytotoxic Toxicity 0.000 description 5
- 230000000885 phytotoxic effect Effects 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- 235000007319 Avena orientalis Nutrition 0.000 description 4
- 244000056139 Brassica cretica Species 0.000 description 4
- 235000003351 Brassica cretica Nutrition 0.000 description 4
- 235000003343 Brassica rupestris Nutrition 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- 244000058871 Echinochloa crus-galli Species 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 239000000428 dust Substances 0.000 description 4
- 235000010460 mustard Nutrition 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 238000012216 screening Methods 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- XHIDCUBUPXIGRV-UHFFFAOYSA-N 3-chloro-4-(chloromethyl)pyrrolidin-2-one Chemical compound ClCC1CNC(=O)C1Cl XHIDCUBUPXIGRV-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- 235000009393 Avena byzantina Nutrition 0.000 description 3
- 235000015225 Panicum colonum Nutrition 0.000 description 3
- 244000046052 Phaseolus vulgaris Species 0.000 description 3
- 208000027418 Wounds and injury Diseases 0.000 description 3
- 239000002671 adjuvant Substances 0.000 description 3
- QKSKPIVNLNLAAV-UHFFFAOYSA-N bis(2-chloroethyl) sulfide Chemical compound ClCCSCCCl QKSKPIVNLNLAAV-UHFFFAOYSA-N 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 208000014674 injury Diseases 0.000 description 3
- DGJLLKBHFCFOOZ-UHFFFAOYSA-N n-prop-2-enyl-3-(trifluoromethyl)aniline Chemical compound FC(F)(F)C1=CC=CC(NCC=C)=C1 DGJLLKBHFCFOOZ-UHFFFAOYSA-N 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 239000002002 slurry Substances 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- FEOZBZXSEJHJJL-UHFFFAOYSA-N 1-benzyl-3-chloro-4-(chloromethyl)pyrrolidin-2-one Chemical compound O=C1C(Cl)C(CCl)CN1CC1=CC=CC=C1 FEOZBZXSEJHJJL-UHFFFAOYSA-N 0.000 description 2
- VURDGHVFUCCHAQ-UHFFFAOYSA-N 1-butyl-3-chloro-4-(chloromethyl)pyrrolidin-2-one Chemical compound CCCCN1CC(CCl)C(Cl)C1=O VURDGHVFUCCHAQ-UHFFFAOYSA-N 0.000 description 2
- WWINJKYFUBEFBE-UHFFFAOYSA-N 2,2-dichloro-n-prop-2-enyl-n-[3-(trifluoromethyl)phenyl]acetamide Chemical compound FC(F)(F)C1=CC=CC(N(CC=C)C(=O)C(Cl)Cl)=C1 WWINJKYFUBEFBE-UHFFFAOYSA-N 0.000 description 2
- QIKAXUAIAUOSQW-UHFFFAOYSA-N 3-chloro-4-(chloromethyl)-1-prop-2-enylpyrrolidin-2-one Chemical compound ClCC1CN(CC=C)C(=O)C1Cl QIKAXUAIAUOSQW-UHFFFAOYSA-N 0.000 description 2
- VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical compound NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 description 2
- 240000001592 Amaranthus caudatus Species 0.000 description 2
- 235000009328 Amaranthus caudatus Nutrition 0.000 description 2
- 235000013479 Amaranthus retroflexus Nutrition 0.000 description 2
- 244000237956 Amaranthus retroflexus Species 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- FZERHIULMFGESH-UHFFFAOYSA-N N-phenylacetamide Chemical compound CC(=O)NC1=CC=CC=C1 FZERHIULMFGESH-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- 235000010627 Phaseolus vulgaris Nutrition 0.000 description 2
- 229920001213 Polysorbate 20 Polymers 0.000 description 2
- 235000015422 Rumex crispus ssp. crispus Nutrition 0.000 description 2
- 235000015426 Rumex crispus ssp. fauriei Nutrition 0.000 description 2
- 244000207667 Rumex vesicarius Species 0.000 description 2
- 230000010933 acylation Effects 0.000 description 2
- 238000005917 acylation reaction Methods 0.000 description 2
- 238000013019 agitation Methods 0.000 description 2
- RMRFFCXPLWYOOY-UHFFFAOYSA-N allyl radical Chemical compound [CH2]C=C RMRFFCXPLWYOOY-UHFFFAOYSA-N 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 229940051881 anilide analgesics and antipyretics Drugs 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- 230000006378 damage Effects 0.000 description 2
- FBCCMZVIWNDFMO-UHFFFAOYSA-N dichloroacetyl chloride Chemical compound ClC(Cl)C(Cl)=O FBCCMZVIWNDFMO-UHFFFAOYSA-N 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000003337 fertilizer Substances 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 230000000051 modifying effect Effects 0.000 description 2
- HNIPNANLYHXYDE-UHFFFAOYSA-N n-[3-(trifluoromethyl)phenyl]acetamide Chemical compound CC(=O)NC1=CC=CC(C(F)(F)F)=C1 HNIPNANLYHXYDE-UHFFFAOYSA-N 0.000 description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- SNAUETXKUXDMFB-UHFFFAOYSA-N n-prop-2-enylbutan-1-amine Chemical compound CCCCNCC=C SNAUETXKUXDMFB-UHFFFAOYSA-N 0.000 description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 239000000123 paper Substances 0.000 description 2
- 230000008635 plant growth Effects 0.000 description 2
- 239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 description 2
- 235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- 230000008707 rearrangement Effects 0.000 description 2
- 238000012552 review Methods 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000004576 sand Substances 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 241000894007 species Species 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 238000005303 weighing Methods 0.000 description 2
- 239000000080 wetting agent Substances 0.000 description 2
- OLYMKHFFLBFZGU-UHFFFAOYSA-N 1,2-dimethoxyethane;1-methoxy-2-(2-methoxyethoxy)ethane Chemical compound COCCOC.COCCOCCOC OLYMKHFFLBFZGU-UHFFFAOYSA-N 0.000 description 1
- YOMVZWRELBAFOM-UHFFFAOYSA-N 1-(3-acetylphenyl)-3-chloro-4-(chloromethyl)pyrrolidin-2-one Chemical compound CC(=O)C1=CC=CC(N2C(C(Cl)C(CCl)C2)=O)=C1 YOMVZWRELBAFOM-UHFFFAOYSA-N 0.000 description 1
- OCZJDAYBIVASQZ-UHFFFAOYSA-N 1-(3-bromophenyl)-3-chloro-4-(chloromethyl)pyrrolidin-2-one Chemical compound O=C1C(Cl)C(CCl)CN1C1=CC=CC(Br)=C1 OCZJDAYBIVASQZ-UHFFFAOYSA-N 0.000 description 1
- KEBMRNXDMRFGNV-UHFFFAOYSA-N 1-(chloromethyl)pyrrolidin-2-one Chemical compound ClCN1CCCC1=O KEBMRNXDMRFGNV-UHFFFAOYSA-N 0.000 description 1
- WPWHSFAFEBZWBB-UHFFFAOYSA-N 1-butyl radical Chemical compound [CH2]CCC WPWHSFAFEBZWBB-UHFFFAOYSA-N 0.000 description 1
- ULQYOTCNGSWKOH-UHFFFAOYSA-N 1-chloro-4-(chloromethyl)pyrrolidin-2-one Chemical compound ClCC1CN(Cl)C(=O)C1 ULQYOTCNGSWKOH-UHFFFAOYSA-N 0.000 description 1
- FUJSJWRORKKPAI-UHFFFAOYSA-N 2-(2,4-dichlorophenoxy)acetyl chloride Chemical class ClC(=O)COC1=CC=C(Cl)C=C1Cl FUJSJWRORKKPAI-UHFFFAOYSA-N 0.000 description 1
- PAWQVTBBRAZDMG-UHFFFAOYSA-N 2-(3-bromo-2-fluorophenyl)acetic acid Chemical compound OC(=O)CC1=CC=CC(Br)=C1F PAWQVTBBRAZDMG-UHFFFAOYSA-N 0.000 description 1
- 125000006040 2-hexenyl group Chemical group 0.000 description 1
- 125000006024 2-pentenyl group Chemical group 0.000 description 1
- NHANGIFXYRKPNC-UHFFFAOYSA-N 3,3-dichloro-4-(chloromethyl)-1-ethylpyrrolidin-2-one Chemical compound CCN1CC(CCl)C(Cl)(Cl)C1=O NHANGIFXYRKPNC-UHFFFAOYSA-N 0.000 description 1
- DMLJFAUTAVPLFI-UHFFFAOYSA-N 3-[3,3-dichloro-4-(chloromethyl)-2-oxopyrrolidin-1-yl]benzonitrile Chemical compound O=C1C(Cl)(Cl)C(CCl)CN1C1=CC=CC(C#N)=C1 DMLJFAUTAVPLFI-UHFFFAOYSA-N 0.000 description 1
- GZNGJMFUTVATBN-UHFFFAOYSA-N 3-[3-chloro-4-(chloromethyl)-2-oxopyrrolidin-1-yl]benzonitrile Chemical compound O=C1C(Cl)C(CCl)CN1C1=CC=CC(C#N)=C1 GZNGJMFUTVATBN-UHFFFAOYSA-N 0.000 description 1
- 125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 description 1
- VHZDMGOPMSGTMI-UHFFFAOYSA-N 3-chloro-4-(chloromethyl)-1-(2,3-dibromopropyl)pyrrolidin-2-one Chemical compound ClCC1CN(CC(Br)CBr)C(=O)C1Cl VHZDMGOPMSGTMI-UHFFFAOYSA-N 0.000 description 1
- ZTOTUPXFVNFOSC-UHFFFAOYSA-N 3-chloro-4-(chloromethyl)-1-(2,6-dimethylphenyl)pyrrolidin-2-one Chemical compound CC1=CC=CC(C)=C1N1C(=O)C(Cl)C(CCl)C1 ZTOTUPXFVNFOSC-UHFFFAOYSA-N 0.000 description 1
- IYIBXZDWEFVVSU-UHFFFAOYSA-N 3-chloro-4-(chloromethyl)-1-(2-methylpropyl)pyrrolidin-2-one Chemical compound CC(C)CN1CC(CCl)C(Cl)C1=O IYIBXZDWEFVVSU-UHFFFAOYSA-N 0.000 description 1
- NHCIHIVJULMVAQ-UHFFFAOYSA-N 3-chloro-4-(chloromethyl)-1-(3-chlorophenyl)pyrrolidin-2-one Chemical compound O=C1C(Cl)C(CCl)CN1C1=CC=CC(Cl)=C1 NHCIHIVJULMVAQ-UHFFFAOYSA-N 0.000 description 1
- MSAXDJYWOOYLKU-UHFFFAOYSA-N 3-chloro-4-(chloromethyl)-1-(3-fluorophenyl)pyrrolidin-2-one Chemical compound FC1=CC=CC(N2C(C(Cl)C(CCl)C2)=O)=C1 MSAXDJYWOOYLKU-UHFFFAOYSA-N 0.000 description 1
- FDDDZUXSUNVITC-UHFFFAOYSA-N 3-chloro-4-(chloromethyl)-1-(3-methoxyphenyl)pyrrolidin-2-one Chemical compound COC1=CC=CC(N2C(C(Cl)C(CCl)C2)=O)=C1 FDDDZUXSUNVITC-UHFFFAOYSA-N 0.000 description 1
- AFUIFKXCPNPDHE-UHFFFAOYSA-N 3-chloro-4-(chloromethyl)-1-(3-methylphenyl)pyrrolidin-2-one Chemical compound CC1=CC=CC(N2C(C(Cl)C(CCl)C2)=O)=C1 AFUIFKXCPNPDHE-UHFFFAOYSA-N 0.000 description 1
- XKOOGYFYTJVAJF-UHFFFAOYSA-N 3-chloro-4-(chloromethyl)-1-(3-methylsulfinylphenyl)pyrrolidin-2-one Chemical compound CS(=O)C1=CC=CC(N2C(C(Cl)C(CCl)C2)=O)=C1 XKOOGYFYTJVAJF-UHFFFAOYSA-N 0.000 description 1
- DKOWJPCTAGUACC-UHFFFAOYSA-N 3-chloro-4-(chloromethyl)-1-(3-nitrophenyl)pyrrolidin-2-one Chemical compound [O-][N+](=O)C1=CC=CC(N2C(C(Cl)C(CCl)C2)=O)=C1 DKOWJPCTAGUACC-UHFFFAOYSA-N 0.000 description 1
- HMTZTHNWPLXQEW-UHFFFAOYSA-N 3-chloro-4-(chloromethyl)-1-(4-chlorophenyl)pyrrolidin-2-one Chemical compound O=C1C(Cl)C(CCl)CN1C1=CC=C(Cl)C=C1 HMTZTHNWPLXQEW-UHFFFAOYSA-N 0.000 description 1
- NLGIWQUZJZJHJY-UHFFFAOYSA-N 3-chloro-4-(chloromethyl)-1-(4-methoxyphenyl)pyrrolidin-2-one Chemical compound C1=CC(OC)=CC=C1N1C(=O)C(Cl)C(CCl)C1 NLGIWQUZJZJHJY-UHFFFAOYSA-N 0.000 description 1
- ZXRQQEWGLKBUGK-UHFFFAOYSA-N 3-chloro-4-(chloromethyl)-1-(4-methylphenyl)pyrrolidin-2-one Chemical compound C1=CC(C)=CC=C1N1C(=O)C(Cl)C(CCl)C1 ZXRQQEWGLKBUGK-UHFFFAOYSA-N 0.000 description 1
- LFGYJPTZXAIBRJ-UHFFFAOYSA-N 3-chloro-4-(chloromethyl)-1-(cyclopropylmethyl)pyrrolidin-2-one Chemical compound O=C1C(Cl)C(CCl)CN1CC1CC1 LFGYJPTZXAIBRJ-UHFFFAOYSA-N 0.000 description 1
- IMFGQLHENHLUDF-UHFFFAOYSA-N 3-chloro-4-(chloromethyl)-1-[(4-chlorophenyl)methyl]pyrrolidin-2-one Chemical compound O=C1C(Cl)C(CCl)CN1CC1=CC=C(Cl)C=C1 IMFGQLHENHLUDF-UHFFFAOYSA-N 0.000 description 1
- NJURTPVLPQVNKR-UHFFFAOYSA-N 3-chloro-4-(chloromethyl)-1-[3-(trifluoromethylsulfanyl)phenyl]pyrrolidin-2-one Chemical compound FC(F)(F)SC1=CC=CC(N2C(C(Cl)C(CCl)C2)=O)=C1 NJURTPVLPQVNKR-UHFFFAOYSA-N 0.000 description 1
- XMUWXMNHFJSYSU-UHFFFAOYSA-N 3-chloro-4-(chloromethyl)-1-ethylpyrrolidin-2-one Chemical compound CCN1CC(CCl)C(Cl)C1=O XMUWXMNHFJSYSU-UHFFFAOYSA-N 0.000 description 1
- QITPMQYBHLZNOS-UHFFFAOYSA-N 3-chloro-4-(chloromethyl)-1-methylpyrrolidin-2-one Chemical compound CN1CC(CCl)C(Cl)C1=O QITPMQYBHLZNOS-UHFFFAOYSA-N 0.000 description 1
- QRTCMWASMUSDJF-UHFFFAOYSA-N 3-chloro-4-(chloromethyl)-1-pentylpyrrolidin-2-one Chemical compound CCCCCN1CC(CCl)C(Cl)C1=O QRTCMWASMUSDJF-UHFFFAOYSA-N 0.000 description 1
- FWMJJJCMZPLTNY-UHFFFAOYSA-N 3-chloro-4-(chloromethyl)-1-phenylpyrrolidin-2-one Chemical compound O=C1C(Cl)C(CCl)CN1C1=CC=CC=C1 FWMJJJCMZPLTNY-UHFFFAOYSA-N 0.000 description 1
- BAZMDHDFQHPRSL-UHFFFAOYSA-N 3-chloro-4-(chloromethyl)-1-propylpyrrolidin-2-one Chemical compound CCCN1CC(CCl)C(Cl)C1=O BAZMDHDFQHPRSL-UHFFFAOYSA-N 0.000 description 1
- IQMPOTHZPZIZQO-UHFFFAOYSA-N 3-chloro-4-(chloromethyl)-3-methyl-1-phenylpyrrolidin-2-one Chemical compound O=C1C(C)(Cl)C(CCl)CN1C1=CC=CC=C1 IQMPOTHZPZIZQO-UHFFFAOYSA-N 0.000 description 1
- 125000006041 3-hexenyl group Chemical group 0.000 description 1
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 1
- 235000007320 Avena fatua Nutrition 0.000 description 1
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- 229920000742 Cotton Polymers 0.000 description 1
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
- 101000940468 Drosophila melanogaster COP9 signalosome complex subunit 2 Proteins 0.000 description 1
- GUVLYNGULCJVDO-UHFFFAOYSA-N EPTC Chemical compound CCCN(CCC)C(=O)SCC GUVLYNGULCJVDO-UHFFFAOYSA-N 0.000 description 1
- 241000982822 Ficus obtusifolia Species 0.000 description 1
- 241001495648 Ipomoea cordatotriloba Species 0.000 description 1
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- 239000005574 MCPA Substances 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- 101800000021 N-terminal protease Proteins 0.000 description 1
- JWOLLWQJKQOEOL-UHFFFAOYSA-N OOOOOOOOOOOOO Chemical compound OOOOOOOOOOOOO JWOLLWQJKQOEOL-UHFFFAOYSA-N 0.000 description 1
- HFEFMUSTGZNOPY-UHFFFAOYSA-N OOOOOOOOOOOOOOOO Chemical compound OOOOOOOOOOOOOOOO HFEFMUSTGZNOPY-UHFFFAOYSA-N 0.000 description 1
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- 235000005775 Setaria Nutrition 0.000 description 1
- 241000232088 Setaria <nematode> Species 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- WHKUVVPPKQRRBV-UHFFFAOYSA-N Trasan Chemical compound CC1=CC(Cl)=CC=C1OCC(O)=O WHKUVVPPKQRRBV-UHFFFAOYSA-N 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 235000005373 Uvularia sessilifolia Nutrition 0.000 description 1
- JEDZLBFUGJTJGQ-UHFFFAOYSA-N [Na].COCCO[AlH]OCCOC Chemical compound [Na].COCCO[AlH]OCCOC JEDZLBFUGJTJGQ-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 150000003869 acetamides Chemical class 0.000 description 1
- 229960001413 acetanilide Drugs 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 description 1
- RQVYBGPQFYCBGX-UHFFFAOYSA-N ametryn Chemical compound CCNC1=NC(NC(C)C)=NC(SC)=N1 RQVYBGPQFYCBGX-UHFFFAOYSA-N 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 150000001448 anilines 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
- ZSIQJIWKELUFRJ-UHFFFAOYSA-N azepane Chemical compound C1CCCNCC1 ZSIQJIWKELUFRJ-UHFFFAOYSA-N 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 150000001559 benzoic acids Chemical class 0.000 description 1
- 125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- YYRMJZQKEFZXMX-UHFFFAOYSA-N calcium;phosphoric acid Chemical compound [Ca+2].OP(O)(O)=O.OP(O)(O)=O YYRMJZQKEFZXMX-UHFFFAOYSA-N 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 150000001721 carbon Chemical class 0.000 description 1
- 239000002361 compost Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000004850 cyclobutylmethyl group Chemical group C1(CCC1)C* 0.000 description 1
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 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
- 125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 description 1
- 230000035613 defoliation Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 229940113088 dimethylacetamide Drugs 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 210000003608 fece Anatomy 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000011086 glassine Substances 0.000 description 1
- 208000037824 growth disorder Diseases 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical group 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000003864 humus Substances 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 125000002346 iodo group Chemical group I* 0.000 description 1
- 239000003621 irrigation water Substances 0.000 description 1
- RGXCTRIQQODGIZ-UHFFFAOYSA-O isodesmosine Chemical compound OC(=O)C(N)CCCC[N+]1=CC(CCC(N)C(O)=O)=CC(CCC(N)C(O)=O)=C1CCCC(N)C(O)=O RGXCTRIQQODGIZ-UHFFFAOYSA-O 0.000 description 1
- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000012669 liquid formulation Substances 0.000 description 1
- 239000012263 liquid product Substances 0.000 description 1
- 239000010871 livestock manure Substances 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 1
- 125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000005394 methallyl group Chemical group 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- DEDOPGXGGQYYMW-UHFFFAOYSA-N molinate Chemical compound CCSC(=O)N1CCCCCC1 DEDOPGXGGQYYMW-UHFFFAOYSA-N 0.000 description 1
- WZZBXOMSMQZTAA-UHFFFAOYSA-N n-benzyl-2,2-dichloro-n-prop-2-enylacetamide Chemical compound ClC(Cl)C(=O)N(CC=C)CC1=CC=CC=C1 WZZBXOMSMQZTAA-UHFFFAOYSA-N 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- FCYRUOLTLFYKQY-UHFFFAOYSA-N n-prop-2-enylbutan-1-amine;hydrochloride Chemical compound Cl.CCCCNCC=C FCYRUOLTLFYKQY-UHFFFAOYSA-N 0.000 description 1
- KTJYOKLCBAFHDD-UHFFFAOYSA-N n-prop-2-enylbutanamide Chemical compound CCCC(=O)NCC=C KTJYOKLCBAFHDD-UHFFFAOYSA-N 0.000 description 1
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 238000005192 partition Methods 0.000 description 1
- 238000004810 partition chromatography Methods 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- 125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- CYQAYERJWZKYML-UHFFFAOYSA-N phosphorus pentasulfide Chemical compound S1P(S2)(=S)SP3(=S)SP1(=S)SP2(=S)S3 CYQAYERJWZKYML-UHFFFAOYSA-N 0.000 description 1
- 229910003446 platinum oxide Inorganic materials 0.000 description 1
- 229920000136 polysorbate Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000012419 sodium bis(2-methoxyethoxy)aluminum hydride Substances 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000002426 superphosphate Substances 0.000 description 1
- 150000003558 thiocarbamic acid derivatives Chemical class 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
- NWONKYPBYAMBJT-UHFFFAOYSA-L zinc sulfate Chemical compound [Zn+2].[O-]S([O-])(=O)=O NWONKYPBYAMBJT-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/24—Oxygen or sulfur atoms
- C07D207/26—2-Pyrrolidones
- C07D207/273—2-Pyrrolidones with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to other ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/24—Oxygen or sulfur atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyrrole Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Catalysts (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US56327975A | 1975-03-28 | 1975-03-28 | |
| US56328075A | 1975-03-28 | 1975-03-28 | |
| US05/647,963 US4110105A (en) | 1975-03-28 | 1976-01-09 | Aromatic N-substituted halo-substituted-2-pyrrolidinones and their utility as herbicides |
| US05/647,962 US4069038A (en) | 1975-03-28 | 1976-01-09 | Acyclic and alicyclic N-substituted halo-2-pyrrolidinones and their utility as herbicides |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1076588A true CA1076588A (en) | 1980-04-29 |
Family
ID=27504836
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA248,947A Expired CA1076588A (en) | 1975-03-28 | 1976-03-26 | Acyclic, alicyclic and aromatic n-substituted halo-substituted 2-pyrrolidinones and their utility as herbicides |
Country Status (25)
| Country | Link |
|---|---|
| JP (1) | JPS6011695B2 (en, 2012) |
| AU (1) | AU502662B2 (en, 2012) |
| BE (1) | BE839977A (en, 2012) |
| BG (2) | BG29122A3 (en, 2012) |
| BR (1) | BR7601774A (en, 2012) |
| CA (1) | CA1076588A (en, 2012) |
| CH (1) | CH625394A5 (en, 2012) |
| DD (1) | DD126149A5 (en, 2012) |
| DE (2) | DE2661042C2 (en, 2012) |
| DK (1) | DK145891C (en, 2012) |
| ES (1) | ES446388A1 (en, 2012) |
| FR (1) | FR2305434A1 (en, 2012) |
| GB (1) | GB1522869A (en, 2012) |
| HU (1) | HU179058B (en, 2012) |
| IL (1) | IL49289A (en, 2012) |
| IN (1) | IN143281B (en, 2012) |
| IT (1) | IT1057396B (en, 2012) |
| MX (1) | MX3355E (en, 2012) |
| MY (1) | MY8000091A (en, 2012) |
| NL (1) | NL187313C (en, 2012) |
| NZ (1) | NZ180424A (en, 2012) |
| PH (1) | PH15176A (en, 2012) |
| PL (2) | PL102693B1 (en, 2012) |
| SU (1) | SU942590A3 (en, 2012) |
| YU (1) | YU40279B (en, 2012) |
Families Citing this family (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU527254B2 (en) * | 1979-02-26 | 1983-02-24 | Stauffer Chemical Company | Synergistic herbicides |
| DE3168705D1 (en) * | 1980-12-19 | 1985-03-14 | Ciba Geigy Ag | Fluoropyrrolidinones, process for their preparation, herbicides containing them and their use |
| DK162087C (da) * | 1983-06-16 | 1992-02-24 | Stauffer Chemical Co | Fremgangsmaade til fremstilling af n-arylhalogenpyrrolidoner |
| FI74385C (fi) * | 1983-12-05 | 1988-02-08 | Stauffer Chemical Co | Synergistiska herbicidblandningar av tiokarbamat och pyrrolidonfoerening. |
| FR2589150B2 (fr) * | 1985-10-25 | 1987-11-20 | Rhone Poulenc Spec Chim | Procede de preparation de n alcene-2 yl m.trifluoromethylanilines |
| EP0205391B1 (fr) * | 1985-05-22 | 1988-10-26 | Rhone-Poulenc Chimie | Procédé de préparation de N alcène-2 yl M-trifluorométhylanilines |
| FR2582300B1 (fr) * | 1985-05-22 | 1987-07-10 | Rhone Poulenc Spec Chim | Procede de preparation de n-2 alcene-2 yl m-trifluoromethylanilines |
| FR2625197B1 (fr) * | 1987-12-23 | 1990-04-27 | Rhone Poulenc Chimie | Procede d'acylation d'une n,n-diallylaniline |
| FR2634762B1 (fr) * | 1988-07-29 | 1990-11-02 | Rhone Poulenc Chimie | Procede de preparation de n-allyl et alkyl-anilines |
| US5210305A (en) * | 1988-07-29 | 1993-05-11 | Rhone-Poulenc Chimie | Process for preparing n-alkylanilines and n-allylanilines |
| FR2634761B1 (fr) * | 1988-07-29 | 1990-11-23 | Rhone Poulenc Chimie | Procede de preparation de n-allyl et de n-alkylanilines |
| US5189220A (en) * | 1988-07-29 | 1993-02-23 | Rhone-Poulenc Chimie | Process for preparing N-alkylanilines and N-allylanilines catalyzed by iodides |
| FR2643902B1 (fr) * | 1989-03-03 | 1991-10-11 | Rhone Poulenc Chimie | Procede de preparation de n-allylmetatrifluoromethylaniline |
| JPH02237970A (ja) * | 1989-03-13 | 1990-09-20 | Mitsui Toatsu Chem Inc | ４―エチル―１―（３―トリフルオロメチルフェニル）―２―ピロリジノン誘導体およびこれらを有効成分とする除草剤 |
| FR2663927A1 (fr) * | 1989-06-05 | 1992-01-03 | Rhone Poulenc Chimie | Procede de preparation de n monoalkyl- ou alkenylanilines. |
| JP2728937B2 (ja) * | 1989-06-14 | 1998-03-18 | 三井東圧化学株式会社 | １―（３―置換ベンジル）―３―ハロゲノ―４―（１―ハロゲノアルキル）―２―ピロリジノン誘導体およびこれらを有効成分とする除草剤 |
| ATE160140T1 (de) * | 1990-08-02 | 1997-11-15 | Rhone Poulenc Chimie | Allylierungsreagens und ein es verwendendes herstellungsverfahren |
| FR2665439B1 (fr) * | 1990-08-02 | 1992-11-06 | Rhone Poulenc Chimie | Reactif de n-allylation et procede de synthese d'une n acyl, n allylaniline. |
| US5538985A (en) * | 1994-01-27 | 1996-07-23 | Mitsui Toatsu Chemicals, Inc. | Pyrrolidinone derivatives |
| EP2052612A1 (de) | 2007-10-24 | 2009-04-29 | Bayer CropScience AG | Herbizid-Kombination |
| DE102008037629A1 (de) | 2008-08-14 | 2010-02-18 | Bayer Cropscience Ag | Herbizid-Kombination mit Dimethoxytriazinyl-substituierten Difluormethansulfonylaniliden |
| CN114031536A (zh) * | 2021-12-14 | 2022-02-11 | 青海省农林科学院 | 一种抑制杂草种子萌发及幼苗生长的纯光学异构体化合物及应用 |
| AR129510A1 (es) | 2022-06-03 | 2024-09-04 | Adama Agan Ltd | Nuevas mezclas para la protección de cultivos |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS49134835A (en, 2012) * | 1973-05-08 | 1974-12-25 |
-
1976
- 1976-03-17 HU HU76SA2904A patent/HU179058B/hu unknown
- 1976-03-17 FR FR7607683A patent/FR2305434A1/fr active Granted
- 1976-03-19 JP JP51030778A patent/JPS6011695B2/ja not_active Expired
- 1976-03-23 BR BR7601774A patent/BR7601774A/pt unknown
- 1976-03-23 IN IN510/CAL/1976A patent/IN143281B/en unknown
- 1976-03-23 GB GB11627/76A patent/GB1522869A/en not_active Expired
- 1976-03-24 MX MX000109U patent/MX3355E/es unknown
- 1976-03-24 BE BE7000801A patent/BE839977A/xx not_active IP Right Cessation
- 1976-03-24 PH PH18252A patent/PH15176A/en unknown
- 1976-03-24 CH CH368776A patent/CH625394A5/de not_active IP Right Cessation
- 1976-03-25 DD DD192041A patent/DD126149A5/xx unknown
- 1976-03-25 DE DE2661042A patent/DE2661042C2/de not_active Expired
- 1976-03-25 IL IL49289A patent/IL49289A/xx unknown
- 1976-03-25 BG BG032702A patent/BG29122A3/xx unknown
- 1976-03-25 DE DE2612731A patent/DE2612731C2/de not_active Expired
- 1976-03-25 BG BG033675A patent/BG29135A3/xx unknown
- 1976-03-25 NZ NZ180424A patent/NZ180424A/xx unknown
- 1976-03-26 NL NLAANVRAGE7603193,A patent/NL187313C/xx not_active IP Right Cessation
- 1976-03-26 ES ES446388A patent/ES446388A1/es not_active Expired
- 1976-03-26 IT IT48736/76A patent/IT1057396B/it active
- 1976-03-26 CA CA248,947A patent/CA1076588A/en not_active Expired
- 1976-03-26 YU YU800/76A patent/YU40279B/xx unknown
- 1976-03-26 AU AU12413/76A patent/AU502662B2/en not_active Expired
- 1976-03-26 DK DK135776A patent/DK145891C/da not_active IP Right Cessation
- 1976-03-27 PL PL1976200412A patent/PL102693B1/pl unknown
- 1976-03-27 PL PL1976188292A patent/PL100036B1/pl unknown
- 1976-11-23 SU SU762421801A patent/SU942590A3/ru active
-
1980
- 1980-12-30 MY MY91/80A patent/MY8000091A/xx unknown
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