PL100036B1 - Srodek chwastobojczy - Google Patents
Srodek chwastobojczy Download PDFInfo
- Publication number
- PL100036B1 PL100036B1 PL1976188292A PL18829276A PL100036B1 PL 100036 B1 PL100036 B1 PL 100036B1 PL 1976188292 A PL1976188292 A PL 1976188292A PL 18829276 A PL18829276 A PL 18829276A PL 100036 B1 PL100036 B1 PL 100036B1
- Authority
- PL
- Poland
- Prior art keywords
- chlorine
- atom
- hydrogen
- pyrrolidinone
- radical
- Prior art date
Links
- -1 cycloalkylalkyl radical Chemical class 0.000 claims description 25
- 229910052801 chlorine Chemical group 0.000 claims description 22
- 239000000460 chlorine Substances 0.000 claims description 18
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 14
- 239000001257 hydrogen Substances 0.000 claims description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims description 13
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 12
- 230000002363 herbicidal effect Effects 0.000 claims description 11
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 10
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 9
- 229910052794 bromium Inorganic materials 0.000 claims description 8
- 239000004009 herbicide Substances 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 6
- 239000004480 active ingredient Substances 0.000 claims description 6
- 239000013543 active substance Substances 0.000 claims description 5
- 239000000969 carrier Substances 0.000 claims description 5
- 229910052740 iodine Inorganic materials 0.000 claims description 5
- 239000000203 mixture Substances 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- WZKSXHQDXQKIQJ-UHFFFAOYSA-N F[C](F)F Chemical compound F[C](F)F WZKSXHQDXQKIQJ-UHFFFAOYSA-N 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical group [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims description 3
- 229910052717 sulfur Chemical group 0.000 claims description 3
- KQTOYEUYHXUEDB-UHFFFAOYSA-N 2,2,3,3,3-pentafluoropropanamide Chemical compound NC(=O)C(F)(F)C(F)(F)F KQTOYEUYHXUEDB-UHFFFAOYSA-N 0.000 claims description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 2
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 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 description 2
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 239000011593 sulfur Chemical group 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims 6
- 239000003085 diluting agent Substances 0.000 claims 4
- 125000004430 oxygen atom Chemical group O* 0.000 claims 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 2
- SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical compound [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 claims 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims 1
- SRBFZHDQGSBBOR-IOVATXLUSA-N D-xylopyranose Chemical group O[C@@H]1COC(O)[C@H](O)[C@H]1O SRBFZHDQGSBBOR-IOVATXLUSA-N 0.000 claims 1
- YZCKVEUIGOORGS-IGMARMGPSA-N Protium Chemical group [1H] YZCKVEUIGOORGS-IGMARMGPSA-N 0.000 claims 1
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims 1
- 125000004414 alkyl thio group Chemical group 0.000 claims 1
- RMRFFCXPLWYOOY-UHFFFAOYSA-N allyl radical Chemical group [CH2]C=C RMRFFCXPLWYOOY-UHFFFAOYSA-N 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- 125000001188 haloalkyl group Chemical group 0.000 claims 1
- 125000004434 sulfur atom Chemical group 0.000 claims 1
- 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 claims 1
- 241000196324 Embryophyta Species 0.000 description 20
- 150000001875 compounds Chemical class 0.000 description 10
- 239000003795 chemical substances by application Substances 0.000 description 9
- 239000000243 solution Substances 0.000 description 8
- 230000006378 damage Effects 0.000 description 7
- 239000002689 soil Substances 0.000 description 7
- 238000000034 method Methods 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 5
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- 230000012010 growth Effects 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 125000004429 atom Chemical group 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 241000219198 Brassica Species 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- 241000894007 species Species 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 244000075850 Avena orientalis Species 0.000 description 2
- 235000007319 Avena orientalis Nutrition 0.000 description 2
- 235000003351 Brassica cretica Nutrition 0.000 description 2
- 235000003343 Brassica rupestris Nutrition 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 235000001018 Hibiscus sabdariffa Nutrition 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- 244000046052 Phaseolus vulgaris Species 0.000 description 2
- 235000005291 Rumex acetosa Nutrition 0.000 description 2
- 240000007001 Rumex acetosella Species 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 230000009471 action Effects 0.000 description 2
- 125000002015 acyclic group Chemical group 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 125000002723 alicyclic group Chemical group 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- QKSKPIVNLNLAAV-UHFFFAOYSA-N bis(2-chloroethyl) sulfide Chemical compound ClCCSCCCl QKSKPIVNLNLAAV-UHFFFAOYSA-N 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 235000010460 mustard Nutrition 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 230000001681 protective effect Effects 0.000 description 2
- 235000003513 sheep sorrel Nutrition 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000009331 sowing Methods 0.000 description 2
- 230000007480 spreading Effects 0.000 description 2
- JIHQDMXYYFUGFV-UHFFFAOYSA-N 1,3,5-triazine Chemical compound C1=NC=NC=N1 JIHQDMXYYFUGFV-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
- 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 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
- FCNLUFGIFVQAAB-UHFFFAOYSA-N 3,3-dichloro-4-(chloromethyl)-1-phenylpyrrolidin-2-one Chemical compound O=C1C(Cl)(Cl)C(CCl)CN1C1=CC=CC=C1 FCNLUFGIFVQAAB-UHFFFAOYSA-N 0.000 description 1
- ZTRACGCGNSQXDR-UHFFFAOYSA-N 3,3-dichloro-4-(chloromethyl)pyrrolidin-2-one Chemical compound ClCC1CNC(=O)C1(Cl)Cl ZTRACGCGNSQXDR-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
- 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
- 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
- KTBXYSXKIUJHDJ-UHFFFAOYSA-N 3-chloro-4-(chloromethyl)-1-(3-methylsulfonylphenyl)pyrrolidin-2-one Chemical compound CS(=O)(=O)C1=CC=CC(N2C(C(Cl)C(CCl)C2)=O)=C1 KTBXYSXKIUJHDJ-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
- 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
- PRWRWDSRTHDPPE-UHFFFAOYSA-N 3-chloro-4-(chloromethyl)-1-cyclohexylpyrrolidin-2-one Chemical compound O=C1C(Cl)C(CCl)CN1C1CCCCC1 PRWRWDSRTHDPPE-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
- XHIDCUBUPXIGRV-UHFFFAOYSA-N 3-chloro-4-(chloromethyl)pyrrolidin-2-one Chemical compound ClCC1CNC(=O)C1Cl XHIDCUBUPXIGRV-UHFFFAOYSA-N 0.000 description 1
- NEGMMKYAVYNLCG-UHFFFAOYSA-N 5-ethyl-1-methyl-5-phenylimidazolidine-2,4-dione Chemical compound C=1C=CC=CC=1C1(CC)N(C)C(=O)NC1=O NEGMMKYAVYNLCG-UHFFFAOYSA-N 0.000 description 1
- 244000237956 Amaranthus retroflexus Species 0.000 description 1
- 235000013479 Amaranthus retroflexus Nutrition 0.000 description 1
- 241000272517 Anseriformes Species 0.000 description 1
- 235000011331 Brassica Nutrition 0.000 description 1
- 241000282461 Canis lupus Species 0.000 description 1
- 229920000298 Cellophane Polymers 0.000 description 1
- HSSBORCLYSCBJR-UHFFFAOYSA-N Chloramben Chemical compound NC1=CC(Cl)=CC(C(O)=O)=C1Cl HSSBORCLYSCBJR-UHFFFAOYSA-N 0.000 description 1
- 235000017896 Digitaria Nutrition 0.000 description 1
- 241001303487 Digitaria <clam> Species 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 206010053759 Growth retardation Diseases 0.000 description 1
- 241000207890 Ipomoea purpurea Species 0.000 description 1
- 239000005574 MCPA Substances 0.000 description 1
- 244000088461 Panicum crus-galli Species 0.000 description 1
- 235000011999 Panicum crusgalli Nutrition 0.000 description 1
- 235000010627 Phaseolus vulgaris Nutrition 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 229920001213 Polysorbate 20 Polymers 0.000 description 1
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical group C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 1
- 235000021501 Rumex crispus Nutrition 0.000 description 1
- 244000207667 Rumex vesicarius Species 0.000 description 1
- 235000005775 Setaria Nutrition 0.000 description 1
- 241000232088 Setaria <nematode> Species 0.000 description 1
- WHKUVVPPKQRRBV-UHFFFAOYSA-N Trasan Chemical compound CC1=CC(Cl)=CC=C1OCC(O)=O WHKUVVPPKQRRBV-UHFFFAOYSA-N 0.000 description 1
- 241000243774 Trichinella Species 0.000 description 1
- 150000003869 acetamides Chemical class 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 150000001559 benzoic acids Chemical class 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
- 238000009835 boiling Methods 0.000 description 1
- GNVMUORYQLCPJZ-UHFFFAOYSA-N carbamothioic s-acid Chemical compound NC(S)=O GNVMUORYQLCPJZ-UHFFFAOYSA-N 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 125000004803 chlorobenzyl group Chemical group 0.000 description 1
- 239000002361 compost Substances 0.000 description 1
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 description 1
- 230000035613 defoliation Effects 0.000 description 1
- 210000003298 dental enamel Anatomy 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- NCPDPTXSMJDCIH-UHFFFAOYSA-N dipropylcarbamothioic s-acid Chemical compound CCCN(C(S)=O)CCC NCPDPTXSMJDCIH-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000003337 fertilizer Substances 0.000 description 1
- 239000011737 fluorine Chemical group 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 231100000001 growth retardation Toxicity 0.000 description 1
- 125000005252 haloacyl group Chemical group 0.000 description 1
- 239000003864 humus Substances 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical group II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 239000003621 irrigation water Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000002362 mulch Substances 0.000 description 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical group CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 1
- 230000017066 negative regulation of growth Effects 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 229930000184 phytotoxin Natural products 0.000 description 1
- 230000008636 plant growth process Effects 0.000 description 1
- 239000003123 plant toxin Substances 0.000 description 1
- 235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 description 1
- 239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical group O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- 230000008707 rearrangement Effects 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 229910052702 rhenium Inorganic materials 0.000 description 1
- WUAPFZMCVAUBPE-UHFFFAOYSA-N rhenium atom Chemical compound [Re] WUAPFZMCVAUBPE-UHFFFAOYSA-N 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000001356 surgical procedure Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 150000003558 thiocarbamic acid derivatives Chemical class 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- 125000005034 trifluormethylthio group Chemical group FC(S*)(F)F 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)
- Catalysts (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US56328075A | 1975-03-28 | 1975-03-28 | |
| US56327975A | 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 |
|---|---|
| PL100036B1 true PL100036B1 (pl) | 1978-08-31 |
Family
ID=27504836
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL1976188292A PL100036B1 (pl) | 1975-03-28 | 1976-03-27 | Srodek chwastobojczy |
| PL1976200412A PL102693B1 (pl) | 1975-03-28 | 1976-03-27 | Sposob wytwarzania nowych pochodnych chlorowco-2-pirolidynonu |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL1976200412A PL102693B1 (pl) | 1975-03-28 | 1976-03-27 | Sposob wytwarzania nowych pochodnych chlorowco-2-pirolidynonu |
Country Status (25)
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 |
| EP0055215B1 (de) * | 1980-12-19 | 1985-01-30 | Ciba-Geigy Ag | Neue Fluorpyrrolidinone, Verfahren zu deren Herstellung, sie enthaltende herbizide Mittel und deren Verwendung |
| 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. |
| EP0205391B1 (fr) * | 1985-05-22 | 1988-10-26 | Rhone-Poulenc Chimie | Procédé de préparation de N alcène-2 yl M-trifluorométhylanilines |
| FR2589150B2 (fr) * | 1985-10-25 | 1987-11-20 | Rhone Poulenc Spec Chim | Procede de preparation de n alcene-2 yl m.trifluoromethylanilines |
| 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 |
| FR2634761B1 (fr) * | 1988-07-29 | 1990-11-23 | Rhone Poulenc Chimie | Procede de preparation de n-allyl et de n-alkylanilines |
| US5210305A (en) * | 1988-07-29 | 1993-05-11 | Rhone-Poulenc Chimie | Process for preparing n-alkylanilines and n-allylanilines |
| FR2634762B1 (fr) * | 1988-07-29 | 1990-11-02 | Rhone Poulenc Chimie | Procede de preparation de n-allyl et alkyl-anilines |
| 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 |
| DE69128175T2 (de) * | 1990-08-02 | 1998-05-20 | 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 |
| WO2023233367A1 (en) | 2022-06-03 | 2023-12-07 | Adama Agan Ltd. | Herbicidal mixtures for crop protection |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS49134835A (enrdf_load_stackoverflow) * | 1973-05-08 | 1974-12-25 |
-
1976
- 1976-03-17 FR FR7607683A patent/FR2305434A1/fr active Granted
- 1976-03-17 HU HU76SA2904A patent/HU179058B/hu unknown
- 1976-03-19 JP JP51030778A patent/JPS6011695B2/ja not_active Expired
- 1976-03-23 GB GB11627/76A patent/GB1522869A/en not_active Expired
- 1976-03-23 BR BR7601774A patent/BR7601774A/pt unknown
- 1976-03-23 IN IN510/CAL/1976A patent/IN143281B/en unknown
- 1976-03-24 MX MX000109U patent/MX3355E/es unknown
- 1976-03-24 PH PH18252A patent/PH15176A/en unknown
- 1976-03-24 BE BE7000801A patent/BE839977A/xx not_active IP Right Cessation
- 1976-03-24 CH CH368776A patent/CH625394A5/de not_active IP Right Cessation
- 1976-03-25 NZ NZ180424A patent/NZ180424A/xx unknown
- 1976-03-25 IL IL49289A patent/IL49289A/xx unknown
- 1976-03-25 DE DE2612731A patent/DE2612731C2/de not_active Expired
- 1976-03-25 DD DD192041A patent/DD126149A5/xx unknown
- 1976-03-25 DE DE2661042A patent/DE2661042C2/de not_active Expired
- 1976-03-25 BG BG032702A patent/BG29122A3/xx unknown
- 1976-03-25 BG BG033675A patent/BG29135A3/xx unknown
- 1976-03-26 IT IT48736/76A patent/IT1057396B/it active
- 1976-03-26 NL NLAANVRAGE7603193,A patent/NL187313C/xx not_active IP Right Cessation
- 1976-03-26 AU AU12413/76A patent/AU502662B2/en not_active Expired
- 1976-03-26 YU YU800/76A patent/YU40279B/xx unknown
- 1976-03-26 ES ES446388A patent/ES446388A1/es not_active Expired
- 1976-03-26 DK DK135776A patent/DK145891C/da not_active IP Right Cessation
- 1976-03-26 CA CA248,947A patent/CA1076588A/en not_active Expired
- 1976-03-27 PL PL1976188292A patent/PL100036B1/pl unknown
- 1976-03-27 PL PL1976200412A patent/PL102693B1/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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