BE537873A - - Google Patents
Info
- Publication number
- BE537873A BE537873A BE537873DA BE537873A BE 537873 A BE537873 A BE 537873A BE 537873D A BE537873D A BE 537873DA BE 537873 A BE537873 A BE 537873A
- Authority
- BE
- Belgium
- Prior art keywords
- sep
- tour
- turntable
- phenyl
- malathion
- Prior art date
Links
- -1 alkenyl ester Chemical class 0.000 claims description 124
- 239000000203 mixture Substances 0.000 claims description 49
- 230000000749 insecticidal effect Effects 0.000 claims description 47
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims description 44
- 229910052698 phosphorus Inorganic materials 0.000 claims description 44
- 239000011574 phosphorus Substances 0.000 claims description 43
- 238000000034 method Methods 0.000 claims description 42
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 40
- 229910019142 PO4 Inorganic materials 0.000 claims description 28
- 235000021317 phosphate Nutrition 0.000 claims description 28
- 241000238631 Hexapoda Species 0.000 claims description 24
- 150000001875 compounds Chemical class 0.000 claims description 24
- 239000011885 synergistic combination Substances 0.000 claims description 23
- 150000002894 organic compounds Chemical class 0.000 claims description 22
- 230000002195 synergetic effect Effects 0.000 claims description 18
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 12
- 125000003107 substituted aryl group Chemical group 0.000 claims description 12
- 229910052757 nitrogen Inorganic materials 0.000 claims description 11
- 125000003118 aryl group Chemical group 0.000 claims description 10
- 229910052760 oxygen Inorganic materials 0.000 claims description 8
- 239000001301 oxygen Substances 0.000 claims description 8
- 230000008569 process Effects 0.000 claims description 8
- 229910052717 sulfur Chemical group 0.000 claims description 8
- RYYWUUFWQRZTIU-UHFFFAOYSA-K thiophosphate Chemical compound [O-]P([O-])([O-])=S RYYWUUFWQRZTIU-UHFFFAOYSA-K 0.000 claims description 8
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 7
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 7
- 125000000623 heterocyclic group Chemical group 0.000 claims description 7
- 239000011593 sulfur Chemical group 0.000 claims description 7
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 150000003013 phosphoric acid derivatives Chemical class 0.000 claims description 5
- RYYWUUFWQRZTIU-UHFFFAOYSA-N Thiophosphoric acid Chemical group OP(O)(S)=O RYYWUUFWQRZTIU-UHFFFAOYSA-N 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 3
- GNVMUORYQLCPJZ-UHFFFAOYSA-M Thiocarbamate Chemical compound NC([S-])=O GNVMUORYQLCPJZ-UHFFFAOYSA-M 0.000 claims 1
- 239000002671 adjuvant Substances 0.000 claims 1
- DKVNPHBNOWQYFE-UHFFFAOYSA-N carbamodithioic acid Chemical compound NC(S)=S DKVNPHBNOWQYFE-UHFFFAOYSA-N 0.000 claims 1
- 239000012990 dithiocarbamate Substances 0.000 claims 1
- 239000005949 Malathion Substances 0.000 description 129
- 229960000453 malathion Drugs 0.000 description 129
- JXSJBGJIGXNWCI-UHFFFAOYSA-N diethyl 2-[(dimethoxyphosphorothioyl)thio]succinate Chemical compound CCOC(=O)CC(SP(=S)(OC)OC)C(=O)OCC JXSJBGJIGXNWCI-UHFFFAOYSA-N 0.000 description 93
- 241000257229 Musca <genus> Species 0.000 description 79
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 70
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 64
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 59
- 241001454294 Tetranychus Species 0.000 description 51
- LCCNCVORNKJIRZ-UHFFFAOYSA-N parathion Chemical compound CCOP(=S)(OCC)OC1=CC=C([N+]([O-])=O)C=C1 LCCNCVORNKJIRZ-UHFFFAOYSA-N 0.000 description 38
- 239000000843 powder Substances 0.000 description 37
- FHIVAFMUCKRCQO-UHFFFAOYSA-N diazinon Chemical compound CCOP(=S)(OCC)OC1=CC(C)=NC(C(C)C)=N1 FHIVAFMUCKRCQO-UHFFFAOYSA-N 0.000 description 35
- 241001301805 Epilachna Species 0.000 description 32
- 238000012360 testing method Methods 0.000 description 32
- 241000257159 Musca domestica Species 0.000 description 29
- 241000663915 Anasa Species 0.000 description 26
- 150000004657 carbamic acid derivatives Chemical class 0.000 description 24
- 239000010452 phosphate Substances 0.000 description 23
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 20
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 19
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 19
- 241001454293 Tetranychus urticae Species 0.000 description 16
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 15
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 14
- 239000002253 acid Substances 0.000 description 14
- 229910052739 hydrogen Inorganic materials 0.000 description 14
- 239000001257 hydrogen Substances 0.000 description 14
- 241000663922 Anasa tristis Species 0.000 description 13
- 239000004615 ingredient Substances 0.000 description 11
- 241000239290 Araneae Species 0.000 description 10
- 241000462639 Epilachna varivestis Species 0.000 description 10
- 241000257226 Muscidae Species 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 238000004821 distillation Methods 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 9
- RLBIQVVOMOPOHC-UHFFFAOYSA-N parathion-methyl Chemical compound COP(=S)(OC)OC1=CC=C([N+]([O-])=O)C=C1 RLBIQVVOMOPOHC-UHFFFAOYSA-N 0.000 description 8
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 7
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 description 7
- 150000007513 acids Chemical class 0.000 description 7
- 239000002917 insecticide Substances 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 241001101705 Murgantia Species 0.000 description 6
- 241001101720 Murgantia histrionica Species 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 6
- KWBIXTIBYFUAGV-UHFFFAOYSA-M n-ethylcarbamate Chemical compound CCNC([O-])=O KWBIXTIBYFUAGV-UHFFFAOYSA-M 0.000 description 6
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 6
- 125000006000 trichloroethyl group Chemical group 0.000 description 6
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 5
- 241000721715 Macrosiphum Species 0.000 description 5
- NPPQSCRMBWNHMW-UHFFFAOYSA-N Meprobamate Chemical compound NC(=O)OCC(C)(CCC)COC(N)=O NPPQSCRMBWNHMW-UHFFFAOYSA-N 0.000 description 5
- 125000003342 alkenyl group Chemical group 0.000 description 5
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 5
- 125000001624 naphthyl group Chemical group 0.000 description 5
- 125000006501 nitrophenyl group Chemical group 0.000 description 5
- 125000000714 pyrimidinyl group Chemical group 0.000 description 5
- 238000010998 test method Methods 0.000 description 5
- 125000003944 tolyl group Chemical group 0.000 description 5
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 4
- 101100260565 Dictyostelium discoideum thyA gene Proteins 0.000 description 4
- 241000255925 Diptera Species 0.000 description 4
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- 244000046052 Phaseolus vulgaris Species 0.000 description 4
- 125000005907 alkyl ester group Chemical group 0.000 description 4
- 125000003710 aryl alkyl group Chemical group 0.000 description 4
- 150000007860 aryl ester derivatives Chemical class 0.000 description 4
- ORSVWFJAARXBHC-UHFFFAOYSA-N carbamic acid;phosphoric acid Chemical compound NC(O)=O.OP(O)(O)=O ORSVWFJAARXBHC-UHFFFAOYSA-N 0.000 description 4
- FZFAMSAMCHXGEF-UHFFFAOYSA-N chloro formate Chemical compound ClOC=O FZFAMSAMCHXGEF-UHFFFAOYSA-N 0.000 description 4
- 125000000753 cycloalkyl group Chemical group 0.000 description 4
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 239000012948 isocyanate Substances 0.000 description 4
- 150000002513 isocyanates Chemical class 0.000 description 4
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 4
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- 150000002895 organic esters Chemical class 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 101150068774 thyX gene Proteins 0.000 description 4
- 231100000331 toxic Toxicity 0.000 description 4
- 230000002588 toxic effect Effects 0.000 description 4
- ZKBGPKCNLVHEKT-UHFFFAOYSA-N (2-chlorophenyl)-ethylcarbamic acid Chemical compound CCN(C(O)=O)C1=CC=CC=C1Cl ZKBGPKCNLVHEKT-UHFFFAOYSA-N 0.000 description 3
- SHXGGYLLZCCNAX-UHFFFAOYSA-N (3-chlorophenyl) carbamate Chemical compound NC(=O)OC1=CC=CC(Cl)=C1 SHXGGYLLZCCNAX-UHFFFAOYSA-N 0.000 description 3
- 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 description 3
- JRLTTZUODKEYDH-UHFFFAOYSA-N 8-methylquinoline Chemical group C1=CN=C2C(C)=CC=CC2=C1 JRLTTZUODKEYDH-UHFFFAOYSA-N 0.000 description 3
- 235000010627 Phaseolus vulgaris Nutrition 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- 125000004369 butenyl group Chemical group C(=CCC)* 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 150000002431 hydrogen Chemical class 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 238000012986 modification Methods 0.000 description 3
- 230000004048 modification Effects 0.000 description 3
- 150000002903 organophosphorus compounds Chemical class 0.000 description 3
- SCWKRWCUMCMVPW-UHFFFAOYSA-N phenyl n-methylcarbamate Chemical compound CNC(=O)OC1=CC=CC=C1 SCWKRWCUMCMVPW-UHFFFAOYSA-N 0.000 description 3
- 229960005235 piperonyl butoxide Drugs 0.000 description 3
- 125000004591 piperonyl group Chemical group C(C1=CC=2OCOC2C=C1)* 0.000 description 3
- 125000003226 pyrazolyl group Chemical group 0.000 description 3
- 125000004076 pyridyl group Chemical group 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 241000894007 species Species 0.000 description 3
- 238000010189 synthetic method Methods 0.000 description 3
- 125000000335 thiazolyl group Chemical group 0.000 description 3
- 125000001544 thienyl group Chemical group 0.000 description 3
- 239000003981 vehicle Substances 0.000 description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 3
- 229920002554 vinyl polymer Polymers 0.000 description 3
- JMYYUDYFQLBYRI-UHFFFAOYSA-N (3-methylphenyl) n-ethylcarbamate Chemical compound CCNC(=O)OC1=CC=CC(C)=C1 JMYYUDYFQLBYRI-UHFFFAOYSA-N 0.000 description 2
- QVUXGCDXMKCVSB-UHFFFAOYSA-N (4-nitrophenyl) n-ethylcarbamate Chemical compound CCNC(=O)OC1=CC=C([N+]([O-])=O)C=C1 QVUXGCDXMKCVSB-UHFFFAOYSA-N 0.000 description 2
- OWFJMIVZYSDULZ-PXOLEDIWSA-N (4s,4ar,5s,5ar,6s,12ar)-4-(dimethylamino)-1,5,6,10,11,12a-hexahydroxy-6-methyl-3,12-dioxo-4,4a,5,5a-tetrahydrotetracene-2-carboxamide Chemical compound C1=CC=C2[C@](O)(C)[C@H]3[C@H](O)[C@H]4[C@H](N(C)C)C(=O)C(C(N)=O)=C(O)[C@@]4(O)C(=O)C3=C(O)C2=C1O OWFJMIVZYSDULZ-PXOLEDIWSA-N 0.000 description 2
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 2
- ZGZCJFIPQPMFNK-UHFFFAOYSA-N 2-ethylhexyl n-phenylcarbamate Chemical compound CCCCC(CC)COC(=O)NC1=CC=CC=C1 ZGZCJFIPQPMFNK-UHFFFAOYSA-N 0.000 description 2
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 2
- 235000000832 Ayote Nutrition 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- DBPRUZCKPFOVDV-UHFFFAOYSA-N Clorprenaline hydrochloride Chemical compound O.Cl.CC(C)NCC(O)C1=CC=CC=C1Cl DBPRUZCKPFOVDV-UHFFFAOYSA-N 0.000 description 2
- 235000009854 Cucurbita moschata Nutrition 0.000 description 2
- 240000001980 Cucurbita pepo Species 0.000 description 2
- 235000009804 Cucurbita pepo subsp pepo Nutrition 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- IDCBOTIENDVCBQ-UHFFFAOYSA-N TEPP Chemical compound CCOP(=O)(OCC)OP(=O)(OCC)OCC IDCBOTIENDVCBQ-UHFFFAOYSA-N 0.000 description 2
- 150000005840 aryl radicals Chemical class 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- KXDHJXZQYSOELW-UHFFFAOYSA-N carbonic acid monoamide Natural products NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 2
- 125000000068 chlorophenyl group Chemical group 0.000 description 2
- 230000002301 combined effect Effects 0.000 description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- 230000006378 damage Effects 0.000 description 2
- 238000010410 dusting Methods 0.000 description 2
- CWPWNWCAOJRJJT-UHFFFAOYSA-N ethyl 2-(phenoxycarbonylamino)acetate Chemical compound CCOC(=O)CNC(=O)OC1=CC=CC=C1 CWPWNWCAOJRJJT-UHFFFAOYSA-N 0.000 description 2
- LRJHYQLNLMGEPR-UHFFFAOYSA-N ethyl n,n-di(propan-2-yl)carbamate Chemical compound CCOC(=O)N(C(C)C)C(C)C LRJHYQLNLMGEPR-UHFFFAOYSA-N 0.000 description 2
- SBPHMRSYBPXBIP-UHFFFAOYSA-N ethyl n-(4-nitrophenyl)carbamate Chemical compound CCOC(=O)NC1=CC=C([N+]([O-])=O)C=C1 SBPHMRSYBPXBIP-UHFFFAOYSA-N 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000004459 forage Substances 0.000 description 2
- JDFMACVFWGNZER-UHFFFAOYSA-N furan-2-ylmethylcarbamic acid Chemical compound OC(=O)NCC1=CC=CO1 JDFMACVFWGNZER-UHFFFAOYSA-N 0.000 description 2
- 230000004927 fusion Effects 0.000 description 2
- 150000002540 isothiocyanates Chemical class 0.000 description 2
- UFEJKYYYVXYMMS-UHFFFAOYSA-N methylcarbamic acid Chemical compound CNC(O)=O UFEJKYYYVXYMMS-UHFFFAOYSA-N 0.000 description 2
- YNTOKMNHRPSGFU-UHFFFAOYSA-N n-Propyl carbamate Chemical compound CCCOC(N)=O YNTOKMNHRPSGFU-UHFFFAOYSA-N 0.000 description 2
- CAYISWBEXVUXRO-UHFFFAOYSA-N naphthalen-1-yl n-ethylcarbamate Chemical compound C1=CC=C2C(OC(=O)NCC)=CC=CC2=C1 CAYISWBEXVUXRO-UHFFFAOYSA-N 0.000 description 2
- RYVFWTRZUMJDRI-UHFFFAOYSA-N naphthalen-2-yl n-ethylcarbamate Chemical compound C1=CC=CC2=CC(OC(=O)NCC)=CC=C21 RYVFWTRZUMJDRI-UHFFFAOYSA-N 0.000 description 2
- GHMTYYTXWHINSX-UHFFFAOYSA-N o-phenyl n,n-diethylcarbamothioate Chemical compound CCN(CC)C(=S)OC1=CC=CC=C1 GHMTYYTXWHINSX-UHFFFAOYSA-N 0.000 description 2
- 239000002420 orchard Substances 0.000 description 2
- 125000004430 oxygen atom Chemical group O* 0.000 description 2
- 244000045947 parasite Species 0.000 description 2
- SVWBBVZRYSQHPF-UHFFFAOYSA-N phenyl morpholine-4-carboxylate Chemical compound C1COCCN1C(=O)OC1=CC=CC=C1 SVWBBVZRYSQHPF-UHFFFAOYSA-N 0.000 description 2
- MYOHNZJKOAODMX-UHFFFAOYSA-N phenyl n,n-dimethylcarbamate Chemical compound CN(C)C(=O)OC1=CC=CC=C1 MYOHNZJKOAODMX-UHFFFAOYSA-N 0.000 description 2
- ZHHRCXDYWBPEDA-UHFFFAOYSA-N phenyl n-(4-chlorophenyl)carbamate Chemical compound C1=CC(Cl)=CC=C1NC(=O)OC1=CC=CC=C1 ZHHRCXDYWBPEDA-UHFFFAOYSA-N 0.000 description 2
- UIYOVJRPKYVWTK-UHFFFAOYSA-N phenyl n-(4-hydroxyphenyl)carbamate Chemical compound C1=CC(O)=CC=C1NC(=O)OC1=CC=CC=C1 UIYOVJRPKYVWTK-UHFFFAOYSA-N 0.000 description 2
- FFXFWNLKXAIQRM-UHFFFAOYSA-N phenyl n-benzylcarbamate Chemical compound C=1C=CC=CC=1OC(=O)NCC1=CC=CC=C1 FFXFWNLKXAIQRM-UHFFFAOYSA-N 0.000 description 2
- VXMFUQFJHWRHDL-UHFFFAOYSA-N phenyl n-dodecylcarbamate Chemical compound CCCCCCCCCCCCNC(=O)OC1=CC=CC=C1 VXMFUQFJHWRHDL-UHFFFAOYSA-N 0.000 description 2
- IBFQVIXTCYXVOC-UHFFFAOYSA-N phenyl n-naphthalen-2-ylcarbamate Chemical compound C=1C=C2C=CC=CC2=CC=1NC(=O)OC1=CC=CC=C1 IBFQVIXTCYXVOC-UHFFFAOYSA-N 0.000 description 2
- FYQGHJHASJALLI-UHFFFAOYSA-N phenyl pyrrolidine-1-carboxylate Chemical compound C1CCCN1C(=O)OC1=CC=CC=C1 FYQGHJHASJALLI-UHFFFAOYSA-N 0.000 description 2
- 150000003017 phosphorus Chemical class 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 235000015136 pumpkin Nutrition 0.000 description 2
- 150000003254 radicals Chemical group 0.000 description 2
- 239000000344 soap Substances 0.000 description 2
- 239000011877 solvent mixture Substances 0.000 description 2
- 239000007921 spray Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- KJAMZCVTJDTESW-UHFFFAOYSA-N tiracizine Chemical compound C1CC2=CC=CC=C2N(C(=O)CN(C)C)C2=CC(NC(=O)OCC)=CC=C21 KJAMZCVTJDTESW-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- QENMPTUFXWVPQZ-UHFFFAOYSA-N (2-hydroxyethylazaniumyl)formate Chemical compound OCCNC(O)=O QENMPTUFXWVPQZ-UHFFFAOYSA-N 0.000 description 1
- BFEJWZZMNLPXLB-UHFFFAOYSA-N (3-chlorophenyl)-propan-2-ylcarbamic acid Chemical compound CC(C)N(C(O)=O)C1=CC=CC(Cl)=C1 BFEJWZZMNLPXLB-UHFFFAOYSA-N 0.000 description 1
- QTILATGINOFTLP-UHFFFAOYSA-N (4-chlorophenyl) n,n-dimethylcarbamate Chemical compound CN(C)C(=O)OC1=CC=C(Cl)C=C1 QTILATGINOFTLP-UHFFFAOYSA-N 0.000 description 1
- PNSRAFGOGJJNSF-UHFFFAOYSA-N (4-chlorophenyl) n-ethylcarbamate Chemical compound CCNC(=O)OC1=CC=C(Cl)C=C1 PNSRAFGOGJJNSF-UHFFFAOYSA-N 0.000 description 1
- QITHMWRZZVHKPY-UHFFFAOYSA-N (4-methylphenyl) n-ethylcarbamate Chemical compound CCNC(=O)OC1=CC=C(C)C=C1 QITHMWRZZVHKPY-UHFFFAOYSA-N 0.000 description 1
- KNTZCGBYFGEMFR-UHFFFAOYSA-N (propan-2-ylazaniumyl)formate Chemical compound CC(C)NC(O)=O KNTZCGBYFGEMFR-UHFFFAOYSA-N 0.000 description 1
- ZTVIKZXZYLEVOL-DGKWVBSXSA-N 2-hydroxy-2-phenylacetic acid [(1R,5S)-8-methyl-8-azabicyclo[3.2.1]octan-3-yl] ester Chemical group C([C@H]1CC[C@@H](C2)N1C)C2OC(=O)C(O)C1=CC=CC=C1 ZTVIKZXZYLEVOL-DGKWVBSXSA-N 0.000 description 1
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- PSTVHRSUNBSVIJ-UHFFFAOYSA-N 5-ethyl-5-hexyl-1,3-diazinane-2,4,6-trione Chemical compound CCCCCCC1(CC)C(=O)NC(=O)NC1=O PSTVHRSUNBSVIJ-UHFFFAOYSA-N 0.000 description 1
- KNIUHBNRWZGIQQ-UHFFFAOYSA-N 7-diethoxyphosphinothioyloxy-4-methylchromen-2-one Chemical compound CC1=CC(=O)OC2=CC(OP(=S)(OCC)OCC)=CC=C21 KNIUHBNRWZGIQQ-UHFFFAOYSA-N 0.000 description 1
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 1
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- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
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- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
- XPPKVPWEQAFLFU-UHFFFAOYSA-N diphosphoric acid Chemical compound OP(O)(=O)OP(O)(O)=O XPPKVPWEQAFLFU-UHFFFAOYSA-N 0.000 description 1
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- FLVVKVHYQBYUHC-UHFFFAOYSA-N ethyl-(4-methoxyphenyl)carbamic acid Chemical compound CCN(C(O)=O)C1=CC=C(OC)C=C1 FLVVKVHYQBYUHC-UHFFFAOYSA-N 0.000 description 1
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- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
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- 239000000463 material Substances 0.000 description 1
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- 230000008018 melting Effects 0.000 description 1
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- RRIWSQXXBIFKQM-UHFFFAOYSA-M n-benzylcarbamate Chemical compound [O-]C(=O)NCC1=CC=CC=C1 RRIWSQXXBIFKQM-UHFFFAOYSA-M 0.000 description 1
- ZZHGIUCYKGFIPV-UHFFFAOYSA-M n-butylcarbamate Chemical compound CCCCNC([O-])=O ZZHGIUCYKGFIPV-UHFFFAOYSA-M 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- YPNZTHVEMNUDND-UHFFFAOYSA-N octyl carbamate Chemical compound CCCCCCCCOC(N)=O YPNZTHVEMNUDND-UHFFFAOYSA-N 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 150000002926 oxygen Chemical class 0.000 description 1
- JQQSUOJIMKJQHS-UHFFFAOYSA-N pentaphenyl group Chemical group C1=CC=CC2=CC3=CC=C4C=C5C=CC=CC5=CC4=C3C=C12 JQQSUOJIMKJQHS-UHFFFAOYSA-N 0.000 description 1
- 125000006187 phenyl benzyl group Chemical group 0.000 description 1
- BSCCSDNZEIHXOK-UHFFFAOYSA-N phenyl carbamate Chemical compound NC(=O)OC1=CC=CC=C1 BSCCSDNZEIHXOK-UHFFFAOYSA-N 0.000 description 1
- QVFDNSVUSCSALT-UHFFFAOYSA-N phenyl n-(2-chlorophenyl)carbamate Chemical compound ClC1=CC=CC=C1NC(=O)OC1=CC=CC=C1 QVFDNSVUSCSALT-UHFFFAOYSA-N 0.000 description 1
- ZGXHYTYJUGGTMG-UHFFFAOYSA-N phenyl n-(2-hydroxyethyl)carbamate Chemical compound OCCNC(=O)OC1=CC=CC=C1 ZGXHYTYJUGGTMG-UHFFFAOYSA-N 0.000 description 1
- NKNMWJCOCJFBJA-UHFFFAOYSA-N phenyl n-(3-methoxypropyl)carbamate Chemical compound COCCCNC(=O)OC1=CC=CC=C1 NKNMWJCOCJFBJA-UHFFFAOYSA-N 0.000 description 1
- VVSQIDMBJAISPY-UHFFFAOYSA-N phenyl n-(furan-2-ylmethyl)carbamate Chemical compound C=1C=CC=CC=1OC(=O)NCC1=CC=CO1 VVSQIDMBJAISPY-UHFFFAOYSA-N 0.000 description 1
- ICGNCPZDLALZBU-UHFFFAOYSA-N phenyl n-butylcarbamate Chemical compound CCCCNC(=O)OC1=CC=CC=C1 ICGNCPZDLALZBU-UHFFFAOYSA-N 0.000 description 1
- KZMHCQUAMFYNRF-UHFFFAOYSA-N phenyl n-ethylcarbamate Chemical compound CCNC(=O)OC1=CC=CC=C1 KZMHCQUAMFYNRF-UHFFFAOYSA-N 0.000 description 1
- XMKAIGDUODXFEL-UHFFFAOYSA-N phenyl n-methyl-n-phenylcarbamate Chemical compound C=1C=CC=CC=1N(C)C(=O)OC1=CC=CC=C1 XMKAIGDUODXFEL-UHFFFAOYSA-N 0.000 description 1
- KSBHJYHUWFFFNA-UHFFFAOYSA-N phenyl n-naphthalen-1-ylcarbamate Chemical compound C=1C=CC2=CC=CC=C2C=1NC(=O)OC1=CC=CC=C1 KSBHJYHUWFFFNA-UHFFFAOYSA-N 0.000 description 1
- XVNKRRXASPPECQ-UHFFFAOYSA-N phenyl n-phenylcarbamate Chemical compound C=1C=CC=CC=1OC(=O)NC1=CC=CC=C1 XVNKRRXASPPECQ-UHFFFAOYSA-N 0.000 description 1
- BKKRNYWSXWYMOW-UHFFFAOYSA-N phenyl n-phenylcarbamodithioate Chemical compound C=1C=CC=CC=1SC(=S)NC1=CC=CC=C1 BKKRNYWSXWYMOW-UHFFFAOYSA-N 0.000 description 1
- RJUVFGTVVVYSFK-UHFFFAOYSA-N phenyl n-propan-2-ylcarbamate Chemical compound CC(C)NC(=O)OC1=CC=CC=C1 RJUVFGTVVVYSFK-UHFFFAOYSA-N 0.000 description 1
- GGZDLAOKPXEJCP-UHFFFAOYSA-N phenyl piperidine-1-carboxylate Chemical compound C1CCCCN1C(=O)OC1=CC=CC=C1 GGZDLAOKPXEJCP-UHFFFAOYSA-N 0.000 description 1
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000003018 phosphorus compounds Chemical class 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- NDVAKXFMBPULSR-UHFFFAOYSA-N propan-2-yl n-cyclohexylcarbamate Chemical compound CC(C)OC(=O)NC1CCCCC1 NDVAKXFMBPULSR-UHFFFAOYSA-N 0.000 description 1
- 229940005657 pyrophosphoric acid Drugs 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- SYAZQKDGCCZTGA-UHFFFAOYSA-N s-phenyl n-ethylcarbamothioate Chemical compound CCNC(=O)SC1=CC=CC=C1 SYAZQKDGCCZTGA-UHFFFAOYSA-N 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000004071 soot Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 230000007480 spreading Effects 0.000 description 1
- 101150018813 ssa1 gene Proteins 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- SEEPANYCNGTZFQ-UHFFFAOYSA-N sulfadiazine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)NC1=NC=CC=N1 SEEPANYCNGTZFQ-UHFFFAOYSA-N 0.000 description 1
- XIUROWKZWPIAIB-UHFFFAOYSA-N sulfotep Chemical compound CCOP(=S)(OCC)OP(=S)(OCC)OCC XIUROWKZWPIAIB-UHFFFAOYSA-N 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 239000012085 test solution Substances 0.000 description 1
- 229910052716 thallium Inorganic materials 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- 239000001585 thymus vulgaris Substances 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Landscapes
- Agricultural Chemicals And Associated Chemicals (AREA)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| BE537873A true BE537873A (cs) |
Family
ID=168087
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BE537873D BE537873A (cs) |
Country Status (1)
| Country | Link |
|---|---|
| BE (1) | BE537873A (cs) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0010178A1 (en) * | 1978-09-20 | 1980-04-30 | Stauffer Chemical Company | Herbicidal compositions which contain a thiocarbamate and an organophosphorous compound and their application |
| US5011526A (en) * | 1978-09-20 | 1991-04-30 | Ici Americas Inc. | Herbicide compositions of extended soil life |
-
0
- BE BE537873D patent/BE537873A/fr unknown
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0010178A1 (en) * | 1978-09-20 | 1980-04-30 | Stauffer Chemical Company | Herbicidal compositions which contain a thiocarbamate and an organophosphorous compound and their application |
| US5011526A (en) * | 1978-09-20 | 1991-04-30 | Ici Americas Inc. | Herbicide compositions of extended soil life |
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