CS227026B2 - Insecticide,acaricide and nematocide compositions and method of preparing active components thereof - Google Patents

Insecticide,acaricide and nematocide compositions and method of preparing active components thereof Download PDF

Info

Publication number: CS227026B2
Authority: CS; Czechoslovakia
Prior art keywords: group; formula; compound; methylcarbamate; dihydro
Prior art date: 1981-06-02

Application number

CS933481A

Other languages

Czech (cs)

English (en)

Inventor

Norio Osaki

Tadateru Murata

Mitsuyasu Kawada

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.)

1981-06-02

Filing date

1981-12-15

Publication date

1984-04-16

1981-12-15 Application filed by Otsuka Chemical Co Ltd filed Critical Otsuka Chemical Co Ltd

1984-04-16 Publication of CS227026B2 publication Critical patent/CS227026B2/cs

Links

238000000034 method Methods 0.000 title claims abstract description 12
239000000203 mixture Substances 0.000 title claims description 54
230000000895 acaricidal effect Effects 0.000 title claims description 6
230000001069 nematicidal effect Effects 0.000 title claims description 5
239000002917 insecticide Substances 0.000 title abstract 2
239000000642 acaricide Substances 0.000 title 1
239000005645 nematicide Substances 0.000 title 1
150000001875 compounds Chemical class 0.000 claims abstract description 68
-1 2, 3-dihydro-2, 2-dimethylbenzofuran-7-yl Chemical group 0.000 claims abstract description 19
125000000217 alkyl group Chemical group 0.000 claims abstract description 16
FWMUJAIKEJWSSY-UHFFFAOYSA-N sulfur dichloride Chemical compound ClSCl FWMUJAIKEJWSSY-UHFFFAOYSA-N 0.000 claims abstract description 12
125000002947 alkylene group Chemical group 0.000 claims abstract description 10
125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 8
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims abstract 2
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 87
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 76
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 33
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 32
125000004432 carbon atom Chemical group C* 0.000 claims description 24
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 22
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 claims description 18
229910052757 nitrogen Inorganic materials 0.000 claims description 17
150000007514 bases Chemical class 0.000 claims description 16
239000004480 active ingredient Substances 0.000 claims description 15
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 14
150000001412 amines Chemical class 0.000 claims description 14
230000000749 insecticidal effect Effects 0.000 claims description 14
239000002904 solvent Substances 0.000 claims description 13
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 11
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 9
DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 claims description 9
GGSUCNLOZRCGPQ-UHFFFAOYSA-N diethylaniline Chemical compound CCN(CC)C1=CC=CC=C1 GGSUCNLOZRCGPQ-UHFFFAOYSA-N 0.000 claims description 9
IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 claims description 9
OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 claims description 8
HVCNXQOWACZAFN-UHFFFAOYSA-N 4-ethylmorpholine Chemical compound CCN1CCOCC1 HVCNXQOWACZAFN-UHFFFAOYSA-N 0.000 claims description 8
JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-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 8
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 7
FNGLQNMQHOAIJQ-UHFFFAOYSA-N Cl[S](Cl)Cl Chemical compound Cl[S](Cl)Cl FNGLQNMQHOAIJQ-UHFFFAOYSA-N 0.000 claims description 6
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 6
HPYNZHMRTTWQTB-UHFFFAOYSA-N dimethylpyridine Natural products CC1=CC=CN=C1C HPYNZHMRTTWQTB-UHFFFAOYSA-N 0.000 claims description 4
229910052736 halogen Inorganic materials 0.000 claims description 4
150000002367 halogens Chemical class 0.000 claims description 4
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 3
KCMQNILKQDQUOY-UHFFFAOYSA-N C1=CC(CN(SCl)C(O)=O)=C2OC(C)(C)CC2=C1 Chemical compound C1=CC(CN(SCl)C(O)=O)=C2OC(C)(C)CC2=C1 KCMQNILKQDQUOY-UHFFFAOYSA-N 0.000 claims description 3
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 3
125000005843 halogen group Chemical group 0.000 claims description 3
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 3
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 3
125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 2
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 2
125000003161 (C1-C6) alkylene group Chemical group 0.000 claims description 2
VIYCMOMZEWDSLK-UHFFFAOYSA-N [butyl-(3-ethoxy-3-oxopropyl)amino]sulfanyl-[(2,2-dimethyl-3H-1-benzofuran-7-yl)methyl]carbamic acid Chemical group CCCCN(CCC(=O)OCC)SN(CC1=CC=CC2=C1OC(C2)(C)C)C(=O)O VIYCMOMZEWDSLK-UHFFFAOYSA-N 0.000 claims description 2
238000004519 manufacturing process Methods 0.000 claims description 2
KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims 4
WHGFMHZZHWXZIX-UHFFFAOYSA-N (2,2-dimethyl-3H-1-benzofuran-7-yl)methyl-[(2-ethoxy-2-oxoethyl)-methylamino]sulfanylcarbamic acid Chemical group CCOC(=O)CN(C)SN(CC1=CC=CC2=C1OC(C2)(C)C)C(=O)O WHGFMHZZHWXZIX-UHFFFAOYSA-N 0.000 claims 1
GPDQXROGIOPZSK-UHFFFAOYSA-N (2,2-dimethyl-3H-1-benzofuran-7-yl)methyl-[(3-ethoxy-3-oxopropyl)-propan-2-ylamino]sulfanylcarbamic acid Chemical group CCOC(=O)CCN(C(C)C)SN(C(O)=O)CC1=CC=CC2=C1OC(C)(C)C2 GPDQXROGIOPZSK-UHFFFAOYSA-N 0.000 claims 1
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
125000004209 (C1-C8) alkyl group Chemical group 0.000 claims 1
WXTMGLCPPBJLRJ-UHFFFAOYSA-N 4-ethylmorpholine pyridine Chemical compound C(C)N1CCOCC1.N1=CC=CC=C1 WXTMGLCPPBJLRJ-UHFFFAOYSA-N 0.000 claims 1
XHTBOZLCXRMJDD-UHFFFAOYSA-N CCCCN(CCC#N)SN(C(O)=O)CC1=CC=CC2=C1OC(C)(C)C2 Chemical group CCCCN(CCC#N)SN(C(O)=O)CC1=CC=CC2=C1OC(C)(C)C2 XHTBOZLCXRMJDD-UHFFFAOYSA-N 0.000 claims 1
DRSHXJFUUPIBHX-UHFFFAOYSA-N COc1ccc(cc1)N1N=CC2C=NC(Nc3cc(OC)c(OC)c(OCCCN4CCN(C)CC4)c3)=NC12 Chemical compound COc1ccc(cc1)N1N=CC2C=NC(Nc3cc(OC)c(OC)c(OCCCN4CCN(C)CC4)c3)=NC12 DRSHXJFUUPIBHX-UHFFFAOYSA-N 0.000 claims 1
LEUZPIQYQHCLND-UHFFFAOYSA-N [cyclohexyl-(3-ethoxy-3-oxopropyl)amino]sulfanyl-[(2,2-dimethyl-3H-1-benzofuran-7-yl)methyl]carbamic acid Chemical group CCOC(=O)CCN(C1CCCCC1)SN(CC2=CC=CC3=C2OC(C3)(C)C)C(=O)O LEUZPIQYQHCLND-UHFFFAOYSA-N 0.000 claims 1
XHHUSSSLQJSOHC-UHFFFAOYSA-N ethyl 2-[[(2,2-dimethyl-3h-1-benzofuran-7-yl)oxycarbonyl-methylamino]sulfanyl-(2-ethoxy-2-oxoethyl)amino]acetate Chemical group CCOC(=O)CN(CC(=O)OCC)SN(C)C(=O)OC1=CC=CC2=C1OC(C)(C)C2 XHHUSSSLQJSOHC-UHFFFAOYSA-N 0.000 claims 1
125000001424 substituent group Chemical group 0.000 claims 1
241001465754 Metazoa Species 0.000 abstract description 6
239000000463 material Substances 0.000 abstract description 2
231100000053 low toxicity Toxicity 0.000 abstract 1
WIDUDNDCBZDPBZ-UHFFFAOYSA-N methyl 3-[[(2,3-dimethyl-1-benzofuran-7-yl)oxycarbonyl-methylamino]sulfanyl-(3-methoxy-3-oxopropyl)amino]propanoate Chemical compound COC(=O)CCN(CCC(=O)OC)SN(C)C(=O)OC1=CC=CC2=C1OC(C)=C2C WIDUDNDCBZDPBZ-UHFFFAOYSA-N 0.000 abstract 1
UFEJKYYYVXYMMS-UHFFFAOYSA-N methylcarbamic acid Chemical class CNC(O)=O UFEJKYYYVXYMMS-UHFFFAOYSA-N 0.000 abstract 1
239000000047 product Substances 0.000 description 41
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 30
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 27
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 24
238000001816 cooling Methods 0.000 description 18
239000000243 solution Substances 0.000 description 18
229910052739 hydrogen Inorganic materials 0.000 description 13
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 13
239000011541 reaction mixture Substances 0.000 description 13
238000002360 preparation method Methods 0.000 description 11
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
229910052799 carbon Inorganic materials 0.000 description 10
238000006243 chemical reaction Methods 0.000 description 10
229960001701 chloroform Drugs 0.000 description 10
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
239000000839 emulsion Substances 0.000 description 9
239000008187 granular material Substances 0.000 description 9
241000196324 Embryophyta Species 0.000 description 8
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241000238631 Hexapoda Species 0.000 description 7
150000004657 carbamic acid derivatives Chemical class 0.000 description 7
241000238876 Acari Species 0.000 description 6
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
239000004927 clay Substances 0.000 description 6
239000013078 crystal Substances 0.000 description 6
239000012535 impurity Substances 0.000 description 6
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230000001988 toxicity Effects 0.000 description 6
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239000003480 eluent Substances 0.000 description 5
125000004494 ethyl ester group Chemical group 0.000 description 5
230000000704 physical effect Effects 0.000 description 5
YOSCIBHNIINXGQ-UHFFFAOYSA-N (2,2-dimethyl-3H-1-benzofuran-7-yl) N-methylcarbamate Chemical compound CNC(=O)OC1=CC=CC2=C1OC(C)(C)C2.CNC(=O)OC1=CC=CC2=C1OC(C)(C)C2 YOSCIBHNIINXGQ-UHFFFAOYSA-N 0.000 description 4
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241000255777 Lepidoptera Species 0.000 description 4
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CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
239000013543 active substance Substances 0.000 description 4
DUEPRVBVGDRKAG-UHFFFAOYSA-N carbofuran Chemical compound CNC(=O)OC1=CC=CC2=C1OC(C)(C)C2 DUEPRVBVGDRKAG-UHFFFAOYSA-N 0.000 description 4
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
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241001149911 Isopoda Species 0.000 description 3
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241000255749 Coccinellidae Species 0.000 description 2
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OJFGRDHUZSJJPB-UHFFFAOYSA-N ethyl 2-(butylamino)acetate Chemical compound CCCCNCC(=O)OCC OJFGRDHUZSJJPB-UHFFFAOYSA-N 0.000 description 2
HJHAOMCORINKOB-UHFFFAOYSA-N ethyl 2-(cyanomethylamino)acetate Chemical compound CCOC(=O)CNCC#N HJHAOMCORINKOB-UHFFFAOYSA-N 0.000 description 2
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KGSVNOLLROCJQM-UHFFFAOYSA-N 2-(benzylamino)acetic acid Chemical compound OC(=O)CNCC1=CC=CC=C1 KGSVNOLLROCJQM-UHFFFAOYSA-N 0.000 description 1
DRPITQSPIKPMTH-UHFFFAOYSA-N 2-(butylamino)-2-methylbutanoic acid Chemical compound CCCCNC(C)(CC)C(O)=O DRPITQSPIKPMTH-UHFFFAOYSA-N 0.000 description 1
DVVNPYAVFWSKAB-UHFFFAOYSA-N 2-(butylazaniumyl)propanoate Chemical compound CCCCNC(C)C(O)=O DVVNPYAVFWSKAB-UHFFFAOYSA-N 0.000 description 1
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JYQWKPMPTMJFCY-UHFFFAOYSA-N 2-(ethoxycarbonylamino)propanoic acid Chemical compound CCOC(=O)NC(C)C(O)=O JYQWKPMPTMJFCY-UHFFFAOYSA-N 0.000 description 1
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NTNZTEQNFHNYBC-UHFFFAOYSA-N ethyl 2-aminoacetate Chemical compound CCOC(=O)CN NTNZTEQNFHNYBC-UHFFFAOYSA-N 0.000 description 1
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AHGQESFVDCNOGJ-UHFFFAOYSA-N ethyl n-(cyanomethyl)carbamate Chemical compound CCOC(=O)NCC#N AHGQESFVDCNOGJ-UHFFFAOYSA-N 0.000 description 1
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NVVZQXQBYZPMLJ-UHFFFAOYSA-N formaldehyde;naphthalene-1-sulfonic acid Chemical compound O=C.C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 NVVZQXQBYZPMLJ-UHFFFAOYSA-N 0.000 description 1
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QPPQHRDVPBTVEV-UHFFFAOYSA-N isopropyl dihydrogen phosphate Chemical compound CC(C)OP(O)(O)=O QPPQHRDVPBTVEV-UHFFFAOYSA-N 0.000 description 1
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DRMGMMWXWKLKAI-UHFFFAOYSA-N methyl n-(cyanomethyl)carbamate Chemical compound COC(=O)NCC#N DRMGMMWXWKLKAI-UHFFFAOYSA-N 0.000 description 1
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IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
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235000009566 rice Nutrition 0.000 description 1
XOVSRHHCHKUFKM-UHFFFAOYSA-N s-methylthiohydroxylamine Chemical compound CSN XOVSRHHCHKUFKM-UHFFFAOYSA-N 0.000 description 1
DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 1
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238000000926 separation method Methods 0.000 description 1
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239000000377 silicon dioxide Substances 0.000 description 1
HFQQZARZPUDIFP-UHFFFAOYSA-M sodium;2-dodecylbenzenesulfonate Chemical compound [Na+].CCCCCCCCCCCCC1=CC=CC=C1S([O-])(=O)=O HFQQZARZPUDIFP-UHFFFAOYSA-M 0.000 description 1
238000000638 solvent extraction Methods 0.000 description 1
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235000011069 sorbitan monooleate Nutrition 0.000 description 1
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238000003756 stirring Methods 0.000 description 1
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150000003512 tertiary amines Chemical class 0.000 description 1
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230000002588 toxic effect Effects 0.000 description 1
235000013311 vegetables Nutrition 0.000 description 1

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Agricultural Chemicals And Associated Chemicals (AREA)
Furan Compounds (AREA)

CS933481A 1981-06-02 1981-12-15 Insecticide,acaricide and nematocide compositions and method of preparing active components thereof CS227026B2 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP8509381A JPS6049637B2 (ja)	1981-06-02	1981-06-02	カ−バメイト系殺虫剤

Publications (1)

Publication Number	Publication Date
CS227026B2 true CS227026B2 (en)	1984-04-16

Family

ID=13848985

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CS933481A CS227026B2 (en)	1981-06-02	1981-12-15	Insecticide,acaricide and nematocide compositions and method of preparing active components thereof

Country Status (2)

Country	Link
JP (1)	JPS6049637B2 (ja)
CS (1)	CS227026B2 (ja)

1981
- 1981-06-02 JP JP8509381A patent/JPS6049637B2/ja not_active Expired
- 1981-12-15 CS CS933481A patent/CS227026B2/cs unknown

Also Published As

Publication number	Publication date
JPS6049637B2 (ja)	1985-11-02
JPS57200376A (en)	1982-12-08

Publication	Publication Date	Title
BR0012224B1 (pt)	2010-12-28	derivado de ftalamida, inseticida agro-hortìcola, e, método para uso de um inseticida agro-hortìcola.
JPH02209868A (ja)	1990-08-21	殺虫性シアノ化合物
US3474171A (en)	1969-10-21	2,2-dimethyl-2,3-dihydrobenzofuranyl-7-n-methylcarbamate
JPS6049638B2 (ja)	1985-11-02	カ−バメイト系殺虫剤
US4444786A (en)	1984-04-24	Carbamate derivatives, insecticidal, miticidal or nematocidal compositions containing the same, and process for preparing the same
US4413005A (en)	1983-11-01	Carbamate derivatives and insecticidal, miticidal or nematocidal compositions containing the same
CS227026B2 (en)	1984-04-16	Insecticide,acaricide and nematocide compositions and method of preparing active components thereof
US4298617A (en)	1981-11-03	Symmetrical and asymmetrical sulfinyl-dicarbamates
US3470236A (en)	1969-09-30	Phenyl-n-methyl carbamic acid esters
GB2084134A (en)	1982-04-07	Insecticidal, miticidal and nematocidal dihydrobenzofuran aminosulphenyl carbabates
CA1170662A (en)	1984-07-10	Carbamate derivatives, process for preparing same and carbamate insecticides
KR850000743B1 (ko)	1985-05-24	카바메이트유도체의 제조방법
US4681874A (en)	1987-07-21	Thiazinephosphonic acid derivatives
US4421693A (en)	1983-12-20	Aminosulfenyl chloride derivatives
US4568671A (en)	1986-02-04	Pesticidal oxime N-alkyl-N-α-(alkylthio-phosphorothio)acyl carbamates
CS208682B2 (en)	1981-09-15	Insecticide,acaricide and nematocide means and method of making its active agent
KR850000629B1 (ko)	1985-05-06	N-설피닐 카바메이트의 제조방법
KR910002882B1 (ko)	1991-05-09	N-메틸카르밤산염의 유도체, 그 제조방법 및 그것을 함유한 살충제
US4350699A (en)	1982-09-21	Pyridylalkoxysulfinyl derivatives of carbamate esters
US4235902A (en)	1980-11-25	Pesticidal carbamate esters of 5-oximino-1,3-oxazolidin-4-ones
US4109011A (en)	1978-08-22	Insecticide carbamates of n-(polychloroallyl)-amino-phenols
NZ201830A (en)	1985-12-13	N-hydrocarbyloxysulphenyl carbamates and herbicidal compositions
US4540708A (en)	1985-09-10	Sulfenyl carbamate derivatives and insecticidal compositions containing the same
KR850000651B1 (ko)	1985-05-07	N-설피닐 카바메이트의 제조방법
US4612326A (en)	1986-09-16	Biocidal sulfur-containing bis-imino carbamate compounds