CA1100138A - Traduction non-disponible - Google Patents

Traduction non-disponible

Info

Publication number: CA1100138A
Authority: CA; Canada
Prior art keywords: compound; octane; trimethyl; azabicyclo; general formula
Prior art date: 1976-07-19
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired

Application number

CA282,400A

Other languages

English (en)

Inventor

Ludwig Nusslein

Friedrich Arndt

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Bayer Pharma AG

Original Assignee

Schering AG

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.)

1976-07-19

Filing date

1977-07-11

Publication date

1981-04-28

1977-07-11 Application filed by Schering AG filed Critical Schering AG

1981-04-28 Application granted granted Critical

1981-04-28 Publication of CA1100138A publication Critical patent/CA1100138A/fr

Status Expired legal-status Critical Current

Links

238000004519 manufacturing process Methods 0.000 title claims description 6
FSAJQNLOJLAWJA-UHFFFAOYSA-N 3,3,5-trimethyl-7-azabicyclo[3.2.1]octane-7-carboxylic acid Chemical class C1C2CC(C)(C)CC1(C)CN2C(O)=O FSAJQNLOJLAWJA-UHFFFAOYSA-N 0.000 title abstract 2
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 9
125000000217 alkyl group Chemical group 0.000 claims abstract description 8
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 8
239000000460 chlorine Substances 0.000 claims abstract description 6
229910052801 chlorine Inorganic materials 0.000 claims abstract description 6
125000001309 chloro group Chemical group Cl* 0.000 claims abstract description 6
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 3
125000003342 alkenyl group Chemical group 0.000 claims abstract description 3
125000003884 phenylalkyl group Chemical group 0.000 claims abstract description 3
125000004430 oxygen atom Chemical group O* 0.000 claims abstract 2
150000001875 compounds Chemical class 0.000 claims description 75
241000196324 Embryophyta Species 0.000 claims description 43
150000002148 esters Chemical class 0.000 claims description 33
238000000034 method Methods 0.000 claims description 29
150000003839 salts Chemical class 0.000 claims description 26
-1 sec.-butyl Chemical group 0.000 claims description 26
230000002633 protecting effect Effects 0.000 claims description 19
239000002253 acid Substances 0.000 claims description 17
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 6
239000002904 solvent Substances 0.000 claims description 6
150000001768 cations Chemical group 0.000 claims description 5
125000005843 halogen group Chemical group 0.000 claims description 5
FRAKHUZTNLUGPB-UHFFFAOYSA-N 3,3,5-trimethyl-7-azabicyclo[3.2.1]octane Chemical compound C1C2NCC1(C)CC(C)(C)C2 FRAKHUZTNLUGPB-UHFFFAOYSA-N 0.000 claims description 4
240000007594 Oryza sativa Species 0.000 claims description 4
235000007164 Oryza sativa Nutrition 0.000 claims description 4
BDAGIHXWWSANSR-UHFFFAOYSA-N formic acid Substances OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 4
235000009566 rice Nutrition 0.000 claims description 4
229920000742 Cotton Polymers 0.000 claims description 3
244000068988 Glycine max Species 0.000 claims description 3
235000010469 Glycine max Nutrition 0.000 claims description 3
244000299507 Gossypium hirsutum Species 0.000 claims description 3
239000011230 binding agent Substances 0.000 claims description 3
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
238000006243 chemical reaction Methods 0.000 claims description 3
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
235000021537 Beetroot Nutrition 0.000 claims description 2
235000011299 Brassica oleracea var botrytis Nutrition 0.000 claims description 2
240000003259 Brassica oleracea var. botrytis Species 0.000 claims description 2
GXKQHVQIPOGQCE-UHFFFAOYSA-N C(C1=CC=CC=C1)SC(=O)N1C2CC(CC(C1)(C2)C)(C)C Chemical compound C(C1=CC=CC=C1)SC(=O)N1C2CC(CC(C1)(C2)C)(C)C GXKQHVQIPOGQCE-UHFFFAOYSA-N 0.000 claims description 2
235000007688 Lycopersicon esculentum Nutrition 0.000 claims description 2
241001300479 Macroptilium Species 0.000 claims description 2
240000003768 Solanum lycopersicum Species 0.000 claims description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical group OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 2
DVKCVIANCITRCB-UHFFFAOYSA-N ethyl 3,3,5-trimethyl-7-azabicyclo[3.2.1]octane-7-carboxylate Chemical compound C1C2N(C(=O)OCC)CC1(C)CC(C)(C)C2 DVKCVIANCITRCB-UHFFFAOYSA-N 0.000 claims description 2
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 2
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
NIXKBAZVOQAHGC-UHFFFAOYSA-N phenylmethanesulfonic acid Chemical group OS(=O)(=O)CC1=CC=CC=C1 NIXKBAZVOQAHGC-UHFFFAOYSA-N 0.000 claims description 2
DJKSTIZKPGOSRU-UHFFFAOYSA-N propan-2-yl 1,3,3-trimethyl-6-azabicyclo[3.2.1]octane-6-carboxylate Chemical compound C(C)(C)OC(=O)N1C2CC(CC(C1)(C2)C)(C)C DJKSTIZKPGOSRU-UHFFFAOYSA-N 0.000 claims description 2
125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 claims 1
AKLYRYABLONWKL-UHFFFAOYSA-N C(CC)SC(=O)N1C2CC(CC(C1)(C2)C)(C)C Chemical compound C(CC)SC(=O)N1C2CC(CC(C1)(C2)C)(C)C AKLYRYABLONWKL-UHFFFAOYSA-N 0.000 claims 1
229940100198 alkylating agent Drugs 0.000 claims 1
239000002168 alkylating agent Substances 0.000 claims 1
OYCAMVFMZLRNQB-UHFFFAOYSA-N benzyl 3,3,5-trimethyl-7-azabicyclo[3.2.1]octane-7-carboxylate Chemical compound C1C(C)(C)CC(C)(C2)CC1N2C(=O)OCC1=CC=CC=C1 OYCAMVFMZLRNQB-UHFFFAOYSA-N 0.000 claims 1
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
125000004369 butenyl group Chemical group C(=CCC)* 0.000 claims 1
PCSKGFZAYDPSAM-UHFFFAOYSA-N butyl 1,3,3-trimethyl-6-azabicyclo[3.2.1]octane-6-carboxylate Chemical compound C(CCC)OC(=O)N1C2CC(CC(C1)(C2)C)(C)C PCSKGFZAYDPSAM-UHFFFAOYSA-N 0.000 claims 1
125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims 1
WTEMRKOGTWVHSU-UHFFFAOYSA-N methyl 3,3,5-trimethyl-7-azabicyclo[3.2.1]octane-7-carboxylate Chemical compound C1C2N(C(=O)OC)CC1(C)CC(C)(C)C2 WTEMRKOGTWVHSU-UHFFFAOYSA-N 0.000 claims 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 1
QOLSPKHUUKOPGN-UHFFFAOYSA-N pentyl 1,3,3-trimethyl-6-azabicyclo[3.2.1]octane-6-carboxylate Chemical compound C(CCCC)OC(=O)N1C2CC(CC(C1)(C2)C)(C)C QOLSPKHUUKOPGN-UHFFFAOYSA-N 0.000 claims 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims 1
ASXGKCNRLLOQFC-UHFFFAOYSA-N phenyl 3,3,5-trimethyl-7-azabicyclo[3.2.1]octane-7-carboxylate Chemical compound C1C(C)(C)CC(C)(C2)CC1N2C(=O)OC1=CC=CC=C1 ASXGKCNRLLOQFC-UHFFFAOYSA-N 0.000 claims 1
JPMDJOHIWJOLCX-UHFFFAOYSA-N prop-2-enyl 3,3,5-trimethyl-7-azabicyclo[3.2.1]octane-7-carboxylate Chemical compound C1C2CC(C)(C)CC1(C)CN2C(=O)OCC=C JPMDJOHIWJOLCX-UHFFFAOYSA-N 0.000 claims 1
AHXZLKCUIKLGHG-UHFFFAOYSA-N propyl 1,3,3-trimethyl-6-azabicyclo[3.2.1]octane-6-carboxylate Chemical compound C(CC)OC(=O)N1C2CC(CC(C1)(C2)C)(C)C AHXZLKCUIKLGHG-UHFFFAOYSA-N 0.000 claims 1
XVHNGCIDVADDBH-UHFFFAOYSA-N s-(4-fluorophenyl) 3,3,5-trimethyl-7-azabicyclo[3.2.1]octane-7-carbothioate Chemical compound C1C(C)(C)CC(C)(C2)CC1N2C(=O)SC1=CC=C(F)C=C1 XVHNGCIDVADDBH-UHFFFAOYSA-N 0.000 claims 1
ZTCBDXOJCDAYDP-UHFFFAOYSA-N s-methyl 3,3,5-trimethyl-7-azabicyclo[3.2.1]octane-7-carbothioate Chemical compound C1C2N(C(=O)SC)CC1(C)CC(C)(C)C2 ZTCBDXOJCDAYDP-UHFFFAOYSA-N 0.000 claims 1
150000001408 amides Chemical class 0.000 description 16
239000013543 active substance Substances 0.000 description 10
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
239000003795 chemical substances by application Substances 0.000 description 7
238000002360 preparation method Methods 0.000 description 7
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
150000007513 acids Chemical class 0.000 description 6
239000002585 base Substances 0.000 description 6
229910052739 hydrogen Inorganic materials 0.000 description 6
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
230000002363 herbicidal effect Effects 0.000 description 5
239000007788 liquid Substances 0.000 description 5
239000000203 mixture Substances 0.000 description 5
229910052757 nitrogen Inorganic materials 0.000 description 5
239000002689 soil Substances 0.000 description 5
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
230000006378 damage Effects 0.000 description 4
HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 4
239000000243 solution Substances 0.000 description 4
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
235000005775 Setaria Nutrition 0.000 description 3
241000232088 Setaria <nematode> Species 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
238000013019 agitation Methods 0.000 description 3
244000038559 crop plants Species 0.000 description 3
239000004009 herbicide Substances 0.000 description 3
150000002576 ketones Chemical class 0.000 description 3
229910052943 magnesium sulfate Inorganic materials 0.000 description 3
235000019341 magnesium sulphate Nutrition 0.000 description 3
239000007787 solid Substances 0.000 description 3
238000003756 stirring Methods 0.000 description 3
239000004094 surface-active agent Substances 0.000 description 3
QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 2
241000192043 Echinochloa Species 0.000 description 2
241000209219 Hordeum Species 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
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
235000021307 Triticum Nutrition 0.000 description 2
241000209140 Triticum Species 0.000 description 2
239000000654 additive Substances 0.000 description 2
229910052784 alkaline earth metal Inorganic materials 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
239000000969 carrier Substances 0.000 description 2
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
150000002170 ethers Chemical class 0.000 description 2
229940052308 general anesthetics halogenated hydrocarbons Drugs 0.000 description 2
150000008282 halocarbons Chemical class 0.000 description 2
229930195733 hydrocarbon Natural products 0.000 description 2
150000002430 hydrocarbons Chemical class 0.000 description 2
239000003921 oil Substances 0.000 description 2
239000012071 phase Substances 0.000 description 2
SIOXPEMLGUPBBT-UHFFFAOYSA-N picolinic acid Chemical class OC(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-N 0.000 description 2
239000000376 reactant Substances 0.000 description 2
239000012429 reaction media Substances 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
238000009331 sowing Methods 0.000 description 2
238000001228 spectrum Methods 0.000 description 2
239000007858 starting material Substances 0.000 description 2
229910052717 sulfur Inorganic materials 0.000 description 2
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
239000008096 xylene Substances 0.000 description 2
FTDGDIFUDKDKAW-UHFFFAOYSA-N 1,1a,5,5a,6,6a-hexahydrocyclopropa[a]indene Chemical class C12C(CC3CC=CC=C13)C2 FTDGDIFUDKDKAW-UHFFFAOYSA-N 0.000 description 1
CSNIZNHTOVFARY-UHFFFAOYSA-N 1,2-benzothiazole Chemical class C1=CC=C2C=NSC2=C1 CSNIZNHTOVFARY-UHFFFAOYSA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
CIEWGZJDEDBECJ-UHFFFAOYSA-N 1-chloro-4-methylbenzene Chemical class [CH2]C1=CC=C(Cl)C=C1 CIEWGZJDEDBECJ-UHFFFAOYSA-N 0.000 description 1
ZLOTYHZOJPLLGG-UHFFFAOYSA-N 1-sulfanylidenethiadiazinane Chemical class S=S1CCCNN1 ZLOTYHZOJPLLGG-UHFFFAOYSA-N 0.000 description 1
ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 2,3-dimethylbutane Chemical group CC(C)C(C)C ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 0.000 description 1
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
IOJSVCXNWBXHIU-UHFFFAOYSA-N 3,3,5-trimethyl-7-azabicyclo[3.2.1]octane-7-carbothioic s-acid Chemical compound C1C2CC(C)(C)CC1(C)CN2C(S)=O IOJSVCXNWBXHIU-UHFFFAOYSA-N 0.000 description 1
YYFLDZZDOUDZQM-UHFFFAOYSA-N 3-[1-[[4-(3-phenylquinolin-2-yl)phenyl]methyl]piperidin-4-yl]-1h-benzimidazol-2-one Chemical compound O=C1NC2=CC=CC=C2N1C(CC1)CCN1CC(C=C1)=CC=C1C1=NC2=CC=CC=C2C=C1C1=CC=CC=C1 YYFLDZZDOUDZQM-UHFFFAOYSA-N 0.000 description 1
241000743985 Alopecurus Species 0.000 description 1
239000005995 Aluminium silicate Substances 0.000 description 1
235000005781 Avena Nutrition 0.000 description 1
244000075850 Avena orientalis Species 0.000 description 1
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
241000905957 Channa melasoma Species 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 1
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
235000019738 Limestone Nutrition 0.000 description 1
241000209082 Lolium Species 0.000 description 1
229910019142 PO4 Inorganic materials 0.000 description 1
QOSMNYMQXIVWKY-UHFFFAOYSA-N Propyl levulinate Chemical compound CCCOC(=O)CCC(C)=O QOSMNYMQXIVWKY-UHFFFAOYSA-N 0.000 description 1
125000000066 S-methyl group Chemical group [H]C([H])([H])S* 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
240000008042 Zea mays Species 0.000 description 1
235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 description 1
235000002017 Zea mays subsp mays Nutrition 0.000 description 1
239000000370 acceptor Substances 0.000 description 1
KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
229940022682 acetone Drugs 0.000 description 1
230000001464 adherent effect Effects 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
150000007933 aliphatic carboxylic acids Chemical class 0.000 description 1
239000003513 alkali Substances 0.000 description 1
150000001342 alkaline earth metals Chemical class 0.000 description 1
BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 description 1
235000012211 aluminium silicate Nutrition 0.000 description 1
150000001448 anilines Chemical class 0.000 description 1
239000000729 antidote Substances 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
BUSBFZWLPXDYIC-UHFFFAOYSA-N arsonic acid Chemical class O[AsH](O)=O BUSBFZWLPXDYIC-UHFFFAOYSA-N 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
JXLHNMVSKXFWAO-UHFFFAOYSA-N azane;7-fluoro-2,1,3-benzoxadiazole-4-sulfonic acid Chemical compound N.OS(=O)(=O)C1=CC=C(F)C2=NON=C12 JXLHNMVSKXFWAO-UHFFFAOYSA-N 0.000 description 1
150000008107 benzenesulfonic acids Chemical class 0.000 description 1
150000001556 benzimidazoles Chemical class 0.000 description 1
125000005605 benzo group Chemical group 0.000 description 1
HAVZTGSQJIEKPI-UHFFFAOYSA-N benzothiadiazine Chemical class C1=CC=C2C=NNSC2=C1 HAVZTGSQJIEKPI-UHFFFAOYSA-N 0.000 description 1
IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical class C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 1
150000005130 benzoxazines Chemical class 0.000 description 1
QXMCNSWZGYKQIK-UHFFFAOYSA-N benzyl 1,3,3-trimethyl-6-azabicyclo[3.2.1]octane-6-carboxylate pentyl 1,3,3-trimethyl-6-azabicyclo[3.2.1]octane-6-carboxylate Chemical compound C(CCCC)OC(=O)N1C2CC(CC(C1)(C2)C)(C)C.C(C2=CC=CC=C2)OC(=O)N2C1CC(CC(C2)(C1)C)(C)C QXMCNSWZGYKQIK-UHFFFAOYSA-N 0.000 description 1
KQLZXRMHQXYLNC-UHFFFAOYSA-N benzyl 2-ethylheptanoate Chemical compound CCCCCC(CC)C(=O)OCC1=CC=CC=C1 KQLZXRMHQXYLNC-UHFFFAOYSA-N 0.000 description 1
150000003842 bromide salts Chemical class 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
229910052791 calcium Inorganic materials 0.000 description 1
239000011575 calcium Substances 0.000 description 1
150000004657 carbamic acid derivatives Chemical class 0.000 description 1
235000013877 carbamide Nutrition 0.000 description 1
DKVNPHBNOWQYFE-UHFFFAOYSA-N carbamodithioic acid Chemical class NC(S)=S DKVNPHBNOWQYFE-UHFFFAOYSA-N 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
150000004649 carbonic acid derivatives Chemical class 0.000 description 1
150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
150000001733 carboxylic acid esters Chemical class 0.000 description 1
235000013339 cereals Nutrition 0.000 description 1
150000001805 chlorine compounds Chemical class 0.000 description 1
KTRFZWJCHOQHMN-UHFFFAOYSA-N chloromethanethioic s-acid Chemical compound SC(Cl)=O KTRFZWJCHOQHMN-UHFFFAOYSA-N 0.000 description 1
150000001991 dicarboxylic acids Chemical class 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
229960001760 dimethyl sulfoxide Drugs 0.000 description 1
239000006185 dispersion Substances 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
230000001804 emulsifying effect Effects 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
QQSGDKKFXBGYON-UHFFFAOYSA-N ethoxy-methylperoxy-(6-methyl-2-propan-2-ylpyrimidin-4-yl)oxy-sulfanylidene-$l^{5}-phosphane Chemical class CCOP(=S)(OOC)OC1=CC(C)=NC(C(C)C)=N1 QQSGDKKFXBGYON-UHFFFAOYSA-N 0.000 description 1
125000000816 ethylene group Chemical class [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
238000000605 extraction Methods 0.000 description 1
235000019253 formic acid Nutrition 0.000 description 1
239000008187 granular material Substances 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
150000002367 halogens Chemical class 0.000 description 1
GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
229940042795 hydrazides for tuberculosis treatment Drugs 0.000 description 1
150000004679 hydroxides Chemical class 0.000 description 1
238000010348 incorporation Methods 0.000 description 1
150000007529 inorganic bases Chemical class 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
150000004694 iodide salts Chemical class 0.000 description 1
NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
230000007775 late Effects 0.000 description 1
229920005610 lignin Polymers 0.000 description 1
239000006028 limestone Substances 0.000 description 1
235000009973 maize Nutrition 0.000 description 1
235000012054 meals Nutrition 0.000 description 1
OSHQMJZDFYTFRT-UHFFFAOYSA-N methyl 2-ethylheptanoate Chemical compound CCCCCC(CC)C(=O)OC OSHQMJZDFYTFRT-UHFFFAOYSA-N 0.000 description 1
239000011707 mineral Substances 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
239000002480 mineral oil Substances 0.000 description 1
235000010446 mineral oil Nutrition 0.000 description 1
BYVCTYDTPSKPRM-UHFFFAOYSA-N naphthalene-1-carbonyl naphthalene-1-carboxylate Chemical compound C1=CC=C2C(C(OC(=O)C=3C4=CC=CC=C4C=CC=3)=O)=CC=CC2=C1 BYVCTYDTPSKPRM-UHFFFAOYSA-N 0.000 description 1
PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical class C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
231100001184 nonphytotoxic Toxicity 0.000 description 1
TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
QNMLMAVEXUCXRG-UHFFFAOYSA-N oxadiazinane-4,5-dione Chemical class O=C1CONNC1=O QNMLMAVEXUCXRG-UHFFFAOYSA-N 0.000 description 1
SDRLFDJOSQLRPB-UHFFFAOYSA-N oxadiazine-4,5-dione Chemical class O=C1CON=NC1=O SDRLFDJOSQLRPB-UHFFFAOYSA-N 0.000 description 1
150000004866 oxadiazoles Chemical class 0.000 description 1
YDCVQGAUCOROHB-UHFFFAOYSA-N oxadiazolidine-4,5-dione Chemical class O=C1NNOC1=O YDCVQGAUCOROHB-UHFFFAOYSA-N 0.000 description 1
210000002741 palatine tonsil Anatomy 0.000 description 1
VATZOGXTPNYUCD-UHFFFAOYSA-N pentyl 2-ethylheptanoate Chemical compound C(CCCC)OC(=O)C(CCCCC)CC VATZOGXTPNYUCD-UHFFFAOYSA-N 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
150000002989 phenols Chemical class 0.000 description 1
IFZYJFGWOZNCPI-UHFFFAOYSA-N phenyl 2-ethylheptanoate Chemical compound CCCCCC(CC)C(=O)OC1=CC=CC=C1 IFZYJFGWOZNCPI-UHFFFAOYSA-N 0.000 description 1
AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 1
150000003009 phosphonic acids Chemical class 0.000 description 1
150000004714 phosphonium salts Chemical class 0.000 description 1
235000011007 phosphoric acid Nutrition 0.000 description 1
150000003016 phosphoric acids Chemical class 0.000 description 1
150000003053 piperidines Chemical class 0.000 description 1
239000000843 powder Substances 0.000 description 1
239000000047 product Substances 0.000 description 1
GIPIQOXJHPZYMD-UHFFFAOYSA-N propyl 2-ethylheptanoate Chemical compound CCCCCC(CC)C(=O)OCCC GIPIQOXJHPZYMD-UHFFFAOYSA-N 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
238000000746 purification Methods 0.000 description 1
150000003217 pyrazoles Chemical group 0.000 description 1
BFZYLUGEHGYJKJ-UHFFFAOYSA-N pyrazolidine-3-thione Chemical class S=C1CCNN1 BFZYLUGEHGYJKJ-UHFFFAOYSA-N 0.000 description 1
150000004892 pyridazines Chemical class 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
150000005299 pyridinones Chemical class 0.000 description 1
150000008318 pyrimidones Chemical class 0.000 description 1
150000003235 pyrrolidines Chemical class 0.000 description 1
150000003254 radicals Chemical group 0.000 description 1
239000013557 residual solvent Substances 0.000 description 1
DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
235000012239 silicon dioxide Nutrition 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000007921 spray Substances 0.000 description 1
125000003011 styrenyl group Chemical class [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
125000003107 substituted aryl group Chemical class 0.000 description 1
125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 1
239000000725 suspension Substances 0.000 description 1
230000002195 synergetic effect Effects 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
235000012222 talc Nutrition 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
150000004867 thiadiazoles Chemical class 0.000 description 1
OLPRIZQBWZMBAS-UHFFFAOYSA-N thiadiazolidine 1,1-dioxide Chemical class O=S1(=O)CCNN1 OLPRIZQBWZMBAS-UHFFFAOYSA-N 0.000 description 1
150000003566 thiocarboxylic acids Chemical class 0.000 description 1
150000003582 thiophosphoric acids Chemical class 0.000 description 1
150000003918 triazines Chemical class 0.000 description 1
150000003852 triazoles Chemical class 0.000 description 1
150000003672 ureas Chemical class 0.000 description 1
235000013311 vegetables Nutrition 0.000 description 1
238000009736 wetting Methods 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1
DYWSVUBJGFTOQC-UHFFFAOYSA-N xi-2-Ethylheptanoic acid Chemical compound CCCCCC(CC)C(O)=O DYWSVUBJGFTOQC-UHFFFAOYSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Indole Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

CA282,400A 1976-07-19 1977-07-11 Traduction non-disponible Expired CA1100138A (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DE19762632915 DE2632915A1 (de)	1976-07-19	1976-07-19	1,3,3-trimethyl-6-azabicyclo- (3.2.1)-octan-6-carbonsaeureester, verfahren zur herstellung dieser verbindungen sowie diese enthaltende herbizide mittel
DEP2632915.7		1976-07-19

Publications (1)

Publication Number	Publication Date
CA1100138A true CA1100138A (fr)	1981-04-28

Family

ID=5983626

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA282,400A Expired CA1100138A (fr)	1976-07-19	1977-07-11	Traduction non-disponible

Country Status (34)

Country	Link
JP (1)	JPS5312855A (fr)
AR (1)	AR216084A1 (fr)
AT (1)	AT355861B (fr)
AU (1)	AU511783B2 (fr)
BE (1)	BE856933A (fr)
BG (2)	BG28027A3 (fr)
BR (1)	BR7704733A (fr)
CA (1)	CA1100138A (fr)
CH (1)	CH627920A5 (fr)
CS (1)	CS192582B2 (fr)
DD (1)	DD131070A5 (fr)
DE (1)	DE2632915A1 (fr)
DK (1)	DK324977A (fr)
ES (1)	ES460737A1 (fr)
FI (1)	FI772095A7 (fr)
FR (1)	FR2359142A1 (fr)
GB (1)	GB1588934A (fr)
GR (1)	GR71649B (fr)
HU (1)	HU178752B (fr)
IE (1)	IE45359B1 (fr)
IL (1)	IL52455A (fr)
IT (1)	IT1113599B (fr)
LU (1)	LU77781A1 (fr)
MX (1)	MX4852E (fr)
NL (1)	NL7707038A (fr)
NO (1)	NO147603C (fr)
PL (1)	PL103690B1 (fr)
PT (1)	PT66822B (fr)
RO (1)	RO71241A (fr)
SE (1)	SE424868B (fr)
SU (1)	SU656464A3 (fr)
TR (1)	TR19833A (fr)
YU (1)	YU164477A (fr)
ZA (1)	ZA774346B (fr)

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
ES303195A1 (es) *	1963-08-19	1965-03-16	Ciba Geigy	Procedimiento para la obtencion de acidos n-(n,n-bicicloalquilenoimino)-ditiocarbonicos.
US3705165A (en) *	1970-08-05	1972-12-05	Elmar Sturm	N-carbonyl derivatives of azabicyclooctanes
US3820974A (en) *	1970-08-05	1974-06-28	Ciba Geigy Corp	Control of weeds with n carbenyl derivatives of azabicyclooctanes

1976
- 1976-07-19 DE DE19762632915 patent/DE2632915A1/de not_active Withdrawn
1977
- 1977-06-24 NL NL7707038A patent/NL7707038A/xx unknown
- 1977-07-01 YU YU01644/77A patent/YU164477A/xx unknown
- 1977-07-04 MX MX77100800U patent/MX4852E/es unknown
- 1977-07-04 CS CS774434A patent/CS192582B2/cs unknown
- 1977-07-05 FI FI772095A patent/FI772095A7/fi not_active Application Discontinuation
- 1977-07-05 IL IL52455A patent/IL52455A/xx unknown
- 1977-07-07 TR TR19833A patent/TR19833A/xx unknown
- 1977-07-11 CA CA282,400A patent/CA1100138A/fr not_active Expired
- 1977-07-14 ES ES460737A patent/ES460737A1/es not_active Expired
- 1977-07-14 AU AU27008/77A patent/AU511783B2/en not_active Expired
- 1977-07-15 DD DD7700200094A patent/DD131070A5/xx unknown
- 1977-07-15 BG BG036916D patent/BG28027A3/xx unknown
- 1977-07-15 CH CH880877A patent/CH627920A5/de not_active IP Right Cessation
- 1977-07-15 BG BG7736916A patent/BG27027A3/xx unknown
- 1977-07-15 IE IE1472/77A patent/IE45359B1/en unknown
- 1977-07-15 LU LU77781A patent/LU77781A1/xx unknown
- 1977-07-16 PL PL1977199694A patent/PL103690B1/pl unknown
- 1977-07-18 GR GR53987A patent/GR71649B/el unknown
- 1977-07-18 DK DK324977A patent/DK324977A/da not_active Application Discontinuation
- 1977-07-18 PT PT66822A patent/PT66822B/pt unknown
- 1977-07-18 AT AT517477A patent/AT355861B/de not_active IP Right Cessation
- 1977-07-18 AR AR268467A patent/AR216084A1/es active
- 1977-07-18 BR BR7704733A patent/BR7704733A/pt unknown
- 1977-07-18 FR FR7721934A patent/FR2359142A1/fr active Granted
- 1977-07-18 NO NO772552A patent/NO147603C/no unknown
- 1977-07-18 HU HU77SCHE615A patent/HU178752B/hu unknown
- 1977-07-18 SE SE7708277A patent/SE424868B/xx unknown
- 1977-07-18 RO RO7791078A patent/RO71241A/fr unknown
- 1977-07-19 GB GB30241/77A patent/GB1588934A/en not_active Expired
- 1977-07-19 JP JP8657277A patent/JPS5312855A/ja active Granted
- 1977-07-19 BE BE179455A patent/BE856933A/fr not_active IP Right Cessation
- 1977-07-19 ZA ZA00774346A patent/ZA774346B/xx unknown
- 1977-07-19 IT IT25888/77A patent/IT1113599B/it active
- 1977-07-19 SU SU772504515A patent/SU656464A3/ru active

Also Published As

Publication number	Publication date
DE2632915A1 (de)	1978-01-26
IL52455A (en)	1981-02-27
HU178752B (en)	1982-06-28
SU656464A3 (ru)	1979-04-05
SE7708277L (sv)	1978-01-20
JPS5312855A (en)	1978-02-04
ES460737A1 (es)	1978-05-01
SE424868B (sv)	1982-08-16
MX4852E (es)	1982-11-01
FR2359142A1 (fr)	1978-02-17
LU77781A1 (fr)	1977-10-17
AU511783B2 (en)	1980-09-04
GR71649B (fr)	1983-06-20
PL103690B1 (pl)	1979-07-31
DD131070A5 (de)	1978-05-31
AT355861B (de)	1980-03-25
FR2359142B1 (fr)	1982-02-19
IL52455A0 (en)	1977-10-31
AU2700877A (en)	1979-01-18
PL199694A1 (pl)	1978-03-13
JPS5510578B2 (fr)	1980-03-17
NO772552L (no)	1978-01-20
BG27027A3 (bg)	1980-02-25
FI772095A7 (fr)	1978-01-20
ZA774346B (en)	1978-06-28
CH627920A5 (en)	1982-02-15
NO147603B (no)	1983-01-31
IT1113599B (it)	1986-01-20
BG28027A3 (bg)	1980-02-25
CS192582B2 (en)	1979-08-31
DK324977A (da)	1978-01-20
AR216084A1 (es)	1979-11-30
IE45359B1 (en)	1982-08-11
RO71241A (fr)	1982-02-01
NL7707038A (nl)	1978-01-23
TR19833A (tr)	1980-01-28
YU164477A (en)	1983-01-21
BE856933A (fr)	1978-01-19
ATA517477A (de)	1979-08-15
PT66822A (de)	1977-08-01
NO147603C (no)	1983-05-11
PT66822B (de)	1978-12-22
IE45359L (en)	1978-01-19
GB1588934A (en)	1981-04-29
BR7704733A (pt)	1978-03-28

Legal Events

Date	Code	Title	Description
1998-04-28	MKEX	Expiry

Publication	Publication Date	Title
EP0104532B1 (fr)	1986-12-03	Dérivés d'un acide o-halobenzoique, leur procédé de préparation, compositions herbicides et leur utilisation
US3828001A (en)	1974-08-06	Thiophene derivatives
KR880001717B1 (ko)	1988-09-08	2-치환페닐 하이단토인유도체의 제조방법
WO1990007500A1 (fr)	1990-07-12	1-phenyl-3-carboxyamidopyrrolidones et leur emploi comme herbicides
EP0219451B1 (fr)	1991-03-20	Semi-carbazones et thiosemi-carbazones
GB1583274A (en)	1981-01-21	Herbicidally active benzodioxole derivatives process for their manufacture and their use
US4923995A (en)	1990-05-08	Pyridylsulfonamides
CA2142463C (fr)	2005-01-18	Pyrazolyloxypicolinamides herbicides
CA1171858A (fr)	1984-07-31	Methode de preparation de 1-amino-1,3,5- triazine-2,4 (1h, 3h)-diones
JPS63201152A (ja)	1988-08-19	シクロヘキサンジオン及びその製造方法並びに該化合物を含有する農薬組成物
US3726948A (en)	1973-04-10	Phosphonamidothioates
US3758481A (en)	1973-09-11	Ridine m-(2,4-dichloro - 5-(haloalkoxy)-phenylcarbomoyl)-pyrrolidine or pipe
CA1110629A (fr)	1981-10-13	Procede industriel d'obtention de derives de 1,2,3- thiadiazolin-2-ide et emploi pour la regulation de la croissance vegetale
US4159902A (en)	1979-07-03	1,3,3-Trimethyl-6-azabicyclo-(3.2.1)-octane-6-carboxylic acid ester, herbicides, process for making same and composition containing same
EP0149269A2 (fr)	1985-07-24	Herbicides hétérocycliques
CA1096379A (fr)	1981-02-24	Traduction non-disponible
JPH08259551A (ja)	1996-10-08	除草性［１，２，４］チアジアゾール類
CA1097673A (fr)	1981-03-17	Traduction non-disponible
CA1090351A (fr)	1980-11-25	Sels de 2-(dimethylcarbamoylimino)-benzthiazoline-3- ide herbicides, procedes de production et utilisation
KR820000116B1 (ko)	1982-02-18	카바민산에스텔의 제조방법
IE45359B1 (en)	1982-08-11	Herbicidally active 1,3,3-trimethyl-6-azabicyclo-(3,2,1)-octane-6-carboxylic acid esters and their manufacture and use
EP0194562B1 (fr)	1990-10-03	Composition fongicide
CA1194882A (fr)	1985-10-08	Derives triazolyliques biologiquement actifs
GB1588158A (en)	1981-04-15	Herbicidally active carbamic acid esters and their manufacture and use
US4210592A (en)	1980-07-01	Thiophosphoro-S-acylated hydrazones