BE892670A - Derives de chlorure d'aminosulfenyle, procede pour leur preparation et procede de preparation de derives de carbamates utiles comme composes insecticides, miticides ou nematocides - Google Patents

Derives de chlorure d'aminosulfenyle, procede pour leur preparation et procede de preparation de derives de carbamates utiles comme composes insecticides, miticides ou nematocides Download PDF

Info

Publication number: BE892670A
Authority: BE; Belgium
Prior art keywords: emi; carbon atoms; group containing; alkyl group; formula
Prior art date: 1981-03-30

Application number

BE0/207691A

Other languages

English (en)

French (fr)

Inventor

N Asai

T Soeda

A Tanaka

T Goto

Original Assignee

Otsuka Chemical Co Ltd

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1981-03-30

Filing date

1982-03-29

Publication date

1982-07-16

1982-03-29 Application filed by Otsuka Chemical Co Ltd filed Critical Otsuka Chemical Co Ltd

1982-07-16 Publication of BE892670A publication Critical patent/BE892670A/fr

Links

238000000034 method Methods 0.000 title claims description 28
238000002360 preparation method Methods 0.000 title claims description 17
ZBVZOMFYISPWMD-UHFFFAOYSA-N amino thiohypochlorite Chemical class NSCl ZBVZOMFYISPWMD-UHFFFAOYSA-N 0.000 title claims description 6
150000001875 compounds Chemical class 0.000 title description 32
239000002917 insecticide Substances 0.000 title description 5
230000001069 nematicidal effect Effects 0.000 title description 3
239000000642 acaricide Substances 0.000 title description 2
150000004657 carbamic acid derivatives Chemical class 0.000 title description 2
239000005645 nematicide Substances 0.000 title description 2
125000004432 carbon atom Chemical group C* 0.000 claims description 64
238000006243 chemical reaction Methods 0.000 claims description 59
125000000217 alkyl group Chemical group 0.000 claims description 34
-1 amino compound Chemical class 0.000 claims description 22
125000003545 alkoxy group Chemical group 0.000 claims description 19
150000007514 bases Chemical class 0.000 claims description 19
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 18
239000002904 solvent Substances 0.000 claims description 16
125000005843 halogen group Chemical group 0.000 claims description 14
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 12
125000002947 alkylene group Chemical group 0.000 claims description 10
PXJJSXABGXMUSU-UHFFFAOYSA-N disulfur dichloride Chemical compound ClSSCl PXJJSXABGXMUSU-UHFFFAOYSA-N 0.000 claims description 10
125000000753 cycloalkyl group Chemical group 0.000 claims description 9
FWMUJAIKEJWSSY-UHFFFAOYSA-N sulfur dichloride Chemical compound ClSCl FWMUJAIKEJWSSY-UHFFFAOYSA-N 0.000 claims description 8
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 7
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 6
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 5
238000005660 chlorination reaction Methods 0.000 claims description 4
125000004429 atom Chemical group 0.000 claims description 3
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 3
239000012320 chlorinating reagent Substances 0.000 claims description 3
239000003795 chemical substances by application Substances 0.000 claims description 2
229910052736 halogen Inorganic materials 0.000 claims description 2
150000002367 halogens Chemical class 0.000 claims description 2
150000001805 chlorine compounds Chemical class 0.000 claims 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
229910052799 carbon Inorganic materials 0.000 claims 1
239000000047 product Substances 0.000 description 51
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 30
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 24
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 21
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 18
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 17
125000004494 ethyl ester group Chemical group 0.000 description 15
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 14
239000000203 mixture Substances 0.000 description 13
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 12
101150041968 CDC13 gene Proteins 0.000 description 10
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 8
239000007858 starting material Substances 0.000 description 8
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 6
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
238000001914 filtration Methods 0.000 description 6
FSYKKLYZXJSNPZ-UHFFFAOYSA-N sarcosine Chemical compound C[NH2+]CC([O-])=O FSYKKLYZXJSNPZ-UHFFFAOYSA-N 0.000 description 6
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
DUEPRVBVGDRKAG-UHFFFAOYSA-N carbofuran Chemical compound CNC(=O)OC1=CC=CC2=C1OC(C)(C)C2 DUEPRVBVGDRKAG-UHFFFAOYSA-N 0.000 description 5
238000004587 chromatography analysis Methods 0.000 description 5
238000001816 cooling Methods 0.000 description 5
239000013078 crystal Substances 0.000 description 5
230000000694 effects Effects 0.000 description 5
239000012156 elution solvent Substances 0.000 description 5
239000012535 impurity Substances 0.000 description 5
239000012452 mother liquor Substances 0.000 description 5
239000000741 silica gel Substances 0.000 description 5
229910002027 silica gel Inorganic materials 0.000 description 5
OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 4
241000238631 Hexapoda Species 0.000 description 4
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 4
238000010438 heat treatment Methods 0.000 description 4
230000000749 insecticidal effect Effects 0.000 description 4
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 4
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
229910052717 sulfur Inorganic materials 0.000 description 4
239000011593 sulfur Substances 0.000 description 4
231100000419 toxicity Toxicity 0.000 description 4
230000001988 toxicity Effects 0.000 description 4
SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 3
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 3
241001465754 Metazoa Species 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
108010077895 Sarcosine Proteins 0.000 description 3
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
238000004458 analytical method Methods 0.000 description 3
239000006227 byproduct Substances 0.000 description 3
POLCUAVZOMRGSN-UHFFFAOYSA-N dipropyl ether Chemical compound CCCOCCC POLCUAVZOMRGSN-UHFFFAOYSA-N 0.000 description 3
150000008282 halocarbons Chemical class 0.000 description 3
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 3
229910000041 hydrogen chloride Inorganic materials 0.000 description 3
229910052938 sodium sulfate Inorganic materials 0.000 description 3
235000011152 sodium sulphate Nutrition 0.000 description 3
238000003756 stirring Methods 0.000 description 3
YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 3
150000003512 tertiary amines Chemical class 0.000 description 3
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 2
BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 2
HVCNXQOWACZAFN-UHFFFAOYSA-N 4-ethylmorpholine Chemical compound CCN1CCOCC1 HVCNXQOWACZAFN-UHFFFAOYSA-N 0.000 description 2
XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 2
241000238876 Acari Species 0.000 description 2
KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
239000004471 Glycine Substances 0.000 description 2
JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 2
OKJIRPAQVSHGFK-UHFFFAOYSA-N N-acetylglycine Chemical compound CC(=O)NCC(O)=O OKJIRPAQVSHGFK-UHFFFAOYSA-N 0.000 description 2
241000244206 Nematoda Species 0.000 description 2
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 2
241000607479 Yersinia pestis Species 0.000 description 2
VFTCEPBUNAKJHC-UHFFFAOYSA-N [acetyloxy(ethyl)amino] acetate Chemical compound CC(=O)ON(CC)OC(C)=O VFTCEPBUNAKJHC-UHFFFAOYSA-N 0.000 description 2
150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
GGSUCNLOZRCGPQ-UHFFFAOYSA-N diethylaniline Chemical compound CCN(CC)C1=CC=CC=C1 GGSUCNLOZRCGPQ-UHFFFAOYSA-N 0.000 description 2
HPYNZHMRTTWQTB-UHFFFAOYSA-N dimethylpyridine Natural products CC1=CC=CN=C1C HPYNZHMRTTWQTB-UHFFFAOYSA-N 0.000 description 2
150000002170 ethers Chemical class 0.000 description 2
JBIONIMUHCHUOW-UHFFFAOYSA-N ethyl 2-(propan-2-ylamino)propanoate Chemical compound CCOC(=O)C(C)NC(C)C JBIONIMUHCHUOW-UHFFFAOYSA-N 0.000 description 2
FKRCODPIKNYEAC-UHFFFAOYSA-N ethyl propionate Chemical compound CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 description 2
229930195733 hydrocarbon Natural products 0.000 description 2
150000002430 hydrocarbons Chemical class 0.000 description 2
NBZBKCUXIYYUSX-UHFFFAOYSA-N iminodiacetic acid Chemical compound OC(=O)CNCC(O)=O NBZBKCUXIYYUSX-UHFFFAOYSA-N 0.000 description 2
239000013067 intermediate product Substances 0.000 description 2
150000004702 methyl esters Chemical class 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
150000003222 pyridines Chemical class 0.000 description 2
239000000725 suspension Substances 0.000 description 2
IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 2
239000008096 xylene Substances 0.000 description 2
NJVJSULZTHOJGT-UHFFFAOYSA-N 2-(4-methoxyanilino)acetic acid Chemical compound COC1=CC=C(NCC(O)=O)C=C1 NJVJSULZTHOJGT-UHFFFAOYSA-N 0.000 description 1
KGSVNOLLROCJQM-UHFFFAOYSA-N 2-(benzylamino)acetic acid Chemical compound OC(=O)CNCC1=CC=CC=C1 KGSVNOLLROCJQM-UHFFFAOYSA-N 0.000 description 1
OJUIRUMDLUMSTN-UHFFFAOYSA-N 2-(benzylamino)acetonitrile;hydrochloride Chemical compound Cl.N#CCNCC1=CC=CC=C1 OJUIRUMDLUMSTN-UHFFFAOYSA-N 0.000 description 1
SPMMZKAWNAKPJM-UHFFFAOYSA-N 2-(butylamino)acetonitrile Chemical compound CCCCNCC#N SPMMZKAWNAKPJM-UHFFFAOYSA-N 0.000 description 1
CTSQFHPACNZECX-UHFFFAOYSA-N 2-(butylamino)propanenitrile Chemical compound CCCCNC(C)C#N CTSQFHPACNZECX-UHFFFAOYSA-N 0.000 description 1
RRWZZMHRVSMLCT-UHFFFAOYSA-N 2-(butylazaniumyl)acetate Chemical compound CCCCNCC(O)=O RRWZZMHRVSMLCT-UHFFFAOYSA-N 0.000 description 1
OQMYZVWIXPPDDE-UHFFFAOYSA-N 2-(cyclohexylazaniumyl)acetate Chemical compound OC(=O)CNC1CCCCC1 OQMYZVWIXPPDDE-UHFFFAOYSA-N 0.000 description 1
RTVSUZHDJGUDGX-UHFFFAOYSA-N 2-(ethoxycarbonylamino)acetic acid Chemical compound CCOC(=O)NCC(O)=O RTVSUZHDJGUDGX-UHFFFAOYSA-N 0.000 description 1
HJHSDOOIPJGRSK-UHFFFAOYSA-N 2-(hexylamino)propanoic acid Chemical compound CCCCCCNC(C)C(O)=O HJHSDOOIPJGRSK-UHFFFAOYSA-N 0.000 description 1
SBJKLBMVVHKFNQ-UHFFFAOYSA-N 2-(methoxycarbonylamino)acetic acid Chemical compound COC(=O)NCC(O)=O SBJKLBMVVHKFNQ-UHFFFAOYSA-N 0.000 description 1
PWWOOVHUFUBBFC-UHFFFAOYSA-N 2-[(2-cyclohexyloxy-2-oxoethyl)amino]acetic acid Chemical compound OC(=O)CNCC(=O)OC1CCCCC1 PWWOOVHUFUBBFC-UHFFFAOYSA-N 0.000 description 1
NRMIXZSQBPZUKE-UHFFFAOYSA-N 2-[(2-cyclopentyloxy-2-oxoethyl)amino]acetic acid Chemical compound OC(=O)CNCC(=O)OC1CCCC1 NRMIXZSQBPZUKE-UHFFFAOYSA-N 0.000 description 1
IJOVAYNEBFHHLP-UHFFFAOYSA-N 2-[(2-cyclopropyloxy-2-oxoethyl)amino]acetic acid Chemical compound OC(=O)CNCC(=O)OC1CC1 IJOVAYNEBFHHLP-UHFFFAOYSA-N 0.000 description 1
QWHBAQJRYFNJFT-UHFFFAOYSA-N 2-[(2-methoxy-2-oxoethyl)azaniumyl]acetate Chemical compound COC(=O)CNCC(O)=O QWHBAQJRYFNJFT-UHFFFAOYSA-N 0.000 description 1
YAQZKMDVZWEZEW-UHFFFAOYSA-N 2-[(2-oxo-2-propan-2-yloxyethyl)amino]acetic acid Chemical compound CC(C)OC(=O)CNCC(O)=O YAQZKMDVZWEZEW-UHFFFAOYSA-N 0.000 description 1
VDKFCCZUCXYILI-UHFFFAOYSA-N 2-[(4-methylphenyl)sulfonylamino]acetic acid Chemical compound CC1=CC=C(S(=O)(=O)NCC(O)=O)C=C1 VDKFCCZUCXYILI-UHFFFAOYSA-N 0.000 description 1
AVRDIJCEUYHYLW-UHFFFAOYSA-N 3-[(3-ethoxy-3-oxopropyl)amino]propanoic acid Chemical compound CCOC(=O)CCNCCC(O)=O AVRDIJCEUYHYLW-UHFFFAOYSA-N 0.000 description 1
LBHSYLSNJGLKSG-UHFFFAOYSA-N 3-[(3-methoxy-3-oxopropyl)amino]propanoic acid Chemical compound COC(=O)CCNCCC(O)=O LBHSYLSNJGLKSG-UHFFFAOYSA-N 0.000 description 1
GNHMRTZZNHZDDM-UHFFFAOYSA-N 3-chloropropionitrile Chemical compound ClCCC#N GNHMRTZZNHZDDM-UHFFFAOYSA-N 0.000 description 1
CKEIQUPFORBNCK-UHFFFAOYSA-N 4-(3-cyanopropylamino)butanenitrile Chemical compound N#CCCCNCCCC#N CKEIQUPFORBNCK-UHFFFAOYSA-N 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
241000254173 Coleoptera Species 0.000 description 1
241000255925 Diptera Species 0.000 description 1
JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
241000258937 Hemiptera Species 0.000 description 1
241001149911 Isopoda Species 0.000 description 1
241000255777 Lepidoptera Species 0.000 description 1
VKZGJEWGVNFKPE-UHFFFAOYSA-N N-Isobutylglycine Chemical compound CC(C)CNCC(O)=O VKZGJEWGVNFKPE-UHFFFAOYSA-N 0.000 description 1
YPIGGYHFMKJNKV-UHFFFAOYSA-N N-ethylglycine Chemical compound CC[NH2+]CC([O-])=O YPIGGYHFMKJNKV-UHFFFAOYSA-N 0.000 description 1
108010065338 N-ethylglycine Proteins 0.000 description 1
241000238814 Orthoptera Species 0.000 description 1
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
241001414989 Thysanoptera Species 0.000 description 1
AKZWRTCWNXHHFR-PDIZUQLASA-N [(3S)-oxolan-3-yl] N-[(2S,3S)-4-[(5S)-5-benzyl-3-[(2R)-2-carbamoyloxy-2,3-dihydro-1H-inden-1-yl]-4-oxo-3H-pyrrol-5-yl]-3-hydroxy-1-phenylbutan-2-yl]carbamate Chemical compound NC(=O)O[C@@H]1Cc2ccccc2C1C1C=N[C@](C[C@H](O)[C@H](Cc2ccccc2)NC(=O)O[C@H]2CCOC2)(Cc2ccccc2)C1=O AKZWRTCWNXHHFR-PDIZUQLASA-N 0.000 description 1
239000000443 aerosol Substances 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
GBZDFUBJNQPZOC-UHFFFAOYSA-N butyl 2-(propan-2-ylamino)propanoate Chemical compound CCCCOC(=O)C(C)NC(C)C GBZDFUBJNQPZOC-UHFFFAOYSA-N 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
239000008199 coating composition Substances 0.000 description 1
238000004440 column chromatography Methods 0.000 description 1
238000010410 dusting Methods 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
HRFATYXNXXEKNO-UHFFFAOYSA-N ethyl 2-(butan-2-ylamino)propanoate Chemical compound CCOC(=O)C(C)NC(C)CC HRFATYXNXXEKNO-UHFFFAOYSA-N 0.000 description 1
DITDYMTYUDGGGF-UHFFFAOYSA-N ethyl 2-(cyanomethylamino)propanoate Chemical compound CCOC(=O)C(C)NCC#N DITDYMTYUDGGGF-UHFFFAOYSA-N 0.000 description 1
OMECLFTURFUIIJ-UHFFFAOYSA-N ethyl 2-(ethoxycarbonylamino)propanoate Chemical compound CCOC(=O)NC(C)C(=O)OCC OMECLFTURFUIIJ-UHFFFAOYSA-N 0.000 description 1
KHRLPZJTPHCMSQ-UHFFFAOYSA-N ethyl 2-(methylamino)propanoate Chemical compound CCOC(=O)C(C)NC KHRLPZJTPHCMSQ-UHFFFAOYSA-N 0.000 description 1
XKFRTCBBCLBPOA-UHFFFAOYSA-N ethyl 2-(propanoylamino)acetate Chemical compound CCOC(=O)CNC(=O)CC XKFRTCBBCLBPOA-UHFFFAOYSA-N 0.000 description 1
KQSPDAGLBCHMTH-UHFFFAOYSA-N ethyl 2-(tert-butylamino)propanoate Chemical compound CCOC(=O)C(C)NC(C)(C)C KQSPDAGLBCHMTH-UHFFFAOYSA-N 0.000 description 1
OZCPYLRDULGVFK-UHFFFAOYSA-N ethyl 2-[chlorosulfanyl-(2-ethoxy-2-oxoethyl)amino]acetate Chemical compound CCOC(=O)CN(SCl)CC(=O)OCC OZCPYLRDULGVFK-UHFFFAOYSA-N 0.000 description 1
AMBDTBHJFINMSE-UHFFFAOYSA-N ethyl 2-acetamidoacetate Chemical compound CCOC(=O)CNC(C)=O AMBDTBHJFINMSE-UHFFFAOYSA-N 0.000 description 1
PTXRQIPIELXJFH-UHFFFAOYSA-N ethyl 2-benzamidoacetate Chemical compound CCOC(=O)CNC(=O)C1=CC=CC=C1 PTXRQIPIELXJFH-UHFFFAOYSA-N 0.000 description 1
FTKLDWGDFWLILC-UHFFFAOYSA-N ethyl 3-[butyl(chlorosulfanyl)amino]propanoate Chemical compound CCCCN(SCl)CCC(=O)OCC FTKLDWGDFWLILC-UHFFFAOYSA-N 0.000 description 1
ATJAIVKHTGMHPH-UHFFFAOYSA-N ethyl 4-[(2-ethoxy-2-oxoethyl)amino]butanoate Chemical compound CCOC(=O)CCCNCC(=O)OCC ATJAIVKHTGMHPH-UHFFFAOYSA-N 0.000 description 1
VEUUMBGHMNQHGO-UHFFFAOYSA-N ethyl chloroacetate Chemical compound CCOC(=O)CCl VEUUMBGHMNQHGO-UHFFFAOYSA-N 0.000 description 1
LXRRVDLNCROODH-UHFFFAOYSA-N ethyl n-(2-cyanoethyl)carbamate Chemical compound CCOC(=O)NCCC#N LXRRVDLNCROODH-UHFFFAOYSA-N 0.000 description 1
239000010419 fine particle Substances 0.000 description 1
239000006260 foam Substances 0.000 description 1
239000002316 fumigant Substances 0.000 description 1
239000008187 granular material Substances 0.000 description 1
231100000086 high toxicity Toxicity 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
125000005928 isopropyloxycarbonyl group Chemical group [H]C([H])([H])C([H])(OC(*)=O)C([H])([H])[H] 0.000 description 1
LSZJHXHDMLYQFO-UHFFFAOYSA-N methyl 2-(propan-2-ylamino)propanoate Chemical compound COC(=O)C(C)NC(C)C LSZJHXHDMLYQFO-UHFFFAOYSA-N 0.000 description 1
XTFWRKOFYMGGRB-UHFFFAOYSA-N methyl 2-[chlorosulfanyl-(2-methoxy-2-oxoethyl)amino]acetate Chemical compound COC(=O)CN(SCl)CC(=O)OC XTFWRKOFYMGGRB-UHFFFAOYSA-N 0.000 description 1
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
239000003094 microcapsule Substances 0.000 description 1
230000003129 miticidal effect Effects 0.000 description 1
238000012986 modification Methods 0.000 description 1
230000004048 modification Effects 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
239000008188 pellet Substances 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
239000000843 powder Substances 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 1
150000003335 secondary amines Chemical class 0.000 description 1
238000000926 separation method Methods 0.000 description 1
238000000638 solvent extraction Methods 0.000 description 1
239000007921 spray Substances 0.000 description 1
229920002994 synthetic fiber Polymers 0.000 description 1
235000013311 vegetables Nutrition 0.000 description 1
239000004563 wettable powder Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
- C07D307/86—Benzo [b] furans; Hydrogenated benzo [b] furans with an oxygen atom directly attached in position 7

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Furan Compounds (AREA)

BE0/207691A 1981-03-30 1982-03-29 Derives de chlorure d'aminosulfenyle, procede pour leur preparation et procede de preparation de derives de carbamates utiles comme composes insecticides, miticides ou nematocides BE892670A (fr)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP56047785A JPS57163360A (en)	1981-03-30	1981-03-30	Bis(alkoxycarbonylmethyl)aminosulphenyl chloride derivative and its preparation

Publications (1)

Publication Number	Publication Date
BE892670A true BE892670A (fr)	1982-07-16

Family

ID=12785023

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
BE0/207691A BE892670A (fr)	1981-03-30	1982-03-29	Derives de chlorure d'aminosulfenyle, procede pour leur preparation et procede de preparation de derives de carbamates utiles comme composes insecticides, miticides ou nematocides

Country Status (4)

Country	Link
JP (1)	JPS57163360A (ja)
BE (1)	BE892670A (ja)
BR (1)	BR8201783A (ja)
ZA (1)	ZA822092B (ja)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4389528A (en) *	1980-10-31	1983-06-21	Fmc Corporation	Trialkylamine/sulfur dioxide catalyzed sulfenylation of carbamates

1981
- 1981-03-30 JP JP56047785A patent/JPS57163360A/ja active Granted
1982
- 1982-03-26 ZA ZA822092A patent/ZA822092B/xx unknown
- 1982-03-29 BE BE0/207691A patent/BE892670A/fr not_active IP Right Cessation
- 1982-03-29 BR BR8201783A patent/BR8201783A/pt not_active IP Right Cessation

Also Published As

Publication number	Publication date
JPS617416B2 (ja)	1986-03-06
BR8201783A (pt)	1983-03-01
JPS57163360A (en)	1982-10-07
ZA822092B (en)	1983-05-25

Legal Events

Date

Code

Title

Description

2000-09-30

RE

Patent lapsed

Owner name: OTSUKA CHEMICAL CO. LTD

Effective date: 20000331

Publication	Publication Date	Title
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CA1237134A (fr)	1988-05-24	Derives de l'acide cyclopropane carboxylique, leur preparation, leur application a la lutte contre les parasites des vegetaux et des locaux, les compositions les renfermant et les nouveaux intermediaires obtenus
FR2670087A1 (fr)	1992-06-12	Utilisation de thiazolylalkoxyacrylates pour la fabrication de compositions insecticides et/ou acaricides.
FR2490636A1 (fr)	1982-03-26	Derives de l'acide carbamique, leur preparation et produits pesticides en contenant
CA1240331A (fr)	1988-08-09	Esters d'acides cyclopropane carboxyliques comportant un groupement cyano, procede de preparation et leur application comme pesticides
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FR2533556A1 (fr)	1984-03-30	Cyclopropane carboxylates a structure allenique, leur procede de preparation et les compositions les renfermant
FR2547581A1 (fr)	1984-12-21	5-amino-3-oxo-4-(phenyle substitue)-2,3-dihydrofuranne et ses derives, leur procede de preparation et leurs applications comme herbicides et substances de croissance des plantes
EP0265305B1 (fr)	1991-06-12	Nouveaux dérivés de la 5-pyrazolone, leur procédé de préparation, leur utilisation comme herbicides et les compositions les renfermant
FR2495609A1 (fr)	1982-06-11	Acylurees, procedes pour les preparer et produits insecticides contenant de tels composes
BE1000110A4 (fr)	1988-03-29	Nouveaux derives d'esters d'acide carbamique, compositions pesticides les contenant et procede pour les preparer.
BE897354A (fr)	1984-01-23	Derives de 1-phenoxy (phenylthio)-4-arylal-kynyloxy-benzene pourvus d'une activite acaricide et d'une activite hormonale juvenile
CH650250A5 (fr)	1985-07-15	Carbamates, procede pour leur preparation et compositions insecticide, miticide ou nematocide les contenant.
EP0557192A1 (fr)	1993-08-25	Esters pyréthrinoides, dérivés de l'alcool 6-(trifluorométhyl)benzylique, leur procédé de préparation et leur application comme pesticides
FR2502616A1 (fr)	1982-10-01	Chlorures d'aminosulfenyle, procede pour leur preparation et leur utilisation dans la preparation de carbamates possedant des proprietes insecticides, miticides ou nematocides
CH649765A5 (fr)	1985-06-14	Derives de carbamate, compositions insecticides, miticides ou nematocides contenant ces derives et procede pour la preparation de ceux-ci.
FR2491062A1 (fr)	1982-04-02	1-carboxy-1- (n - aryl - n - acylamino)-3- (alkyl, alcenyl ou arylalkyl-thio)-propanes eventuellement substitues, leur preparation et leur application a la preparation de gamma-butyro-thio-lactones correspondantes
CA2060770A1 (fr)	1992-08-08	Esters de l'acide 3-(3,3,3-trifluoro 2-chloropropenyl) 2,2-dimethylcyclopropanecarboxylique, leur procede de preparation et leur applications comme pesticides
MC1102A1 (fr)	1977-02-04	Carbamates de phenyle
FR2500452A1 (fr)	1982-08-27	Alcools heterocycliques et derives fonctionnels, ainsi que leur procede de preparation
EP0277052B1 (fr)	1992-03-11	Dérivés de la 4,4-diméthyl tétrahydropyr-2-one, leur procédé de préparation et leur application à la synthèse de produits pyréthrinoides
BE883271R (fr)	1980-11-13	Nouveaux pyrethroides