CA1039294A - N-sulphenylated carbamates and their use as insecticides and acaricides - Google Patents
N-sulphenylated carbamates and their use as insecticides and acaricidesInfo
- Publication number
- CA1039294A CA1039294A CA185,112A CA185112A CA1039294A CA 1039294 A CA1039294 A CA 1039294A CA 185112 A CA185112 A CA 185112A CA 1039294 A CA1039294 A CA 1039294A
- Authority
- CA
- Canada
- Prior art keywords
- compound
- carbon atoms
- formula
- alkyl
- radical
- Prior art date
- 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
Links
- 150000004657 carbamic acid derivatives Chemical class 0.000 title claims description 5
- 230000000895 acaricidal effect Effects 0.000 title description 5
- 239000002917 insecticide Substances 0.000 title description 3
- 239000000642 acaricide Substances 0.000 title description 2
- -1 benzodioxolanyl Chemical group 0.000 claims abstract description 14
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 11
- 125000004414 alkyl thio group Chemical group 0.000 claims abstract description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 4
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract description 3
- 125000004663 dialkyl amino group Chemical group 0.000 claims abstract description 3
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 3
- 229910052739 hydrogen Chemical group 0.000 claims abstract description 3
- 239000001257 hydrogen Chemical group 0.000 claims abstract description 3
- 125000001624 naphthyl group Chemical group 0.000 claims abstract description 3
- 125000003545 alkoxy group Chemical group 0.000 claims abstract 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract 2
- 150000001875 compounds Chemical class 0.000 claims description 42
- 125000004432 carbon atom Chemical group C* 0.000 claims description 14
- 238000002360 preparation method Methods 0.000 claims description 14
- 238000000034 method Methods 0.000 claims description 13
- 241000238631 Hexapoda Species 0.000 claims description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 6
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims description 3
- IMLSAISZLJGWPP-UHFFFAOYSA-N 1,3-dithiolane Chemical group C1CSCS1 IMLSAISZLJGWPP-UHFFFAOYSA-N 0.000 claims description 2
- DTOZRCOCJVVION-UHFFFAOYSA-N O-methyl ethanethioate Chemical compound COC(C)=S DTOZRCOCJVVION-UHFFFAOYSA-N 0.000 claims description 2
- OATSQCXMYKYFQO-UHFFFAOYSA-N S-methyl ethanethioic acid ester Natural products CSC(C)=O OATSQCXMYKYFQO-UHFFFAOYSA-N 0.000 claims description 2
- 125000005879 dioxolanyl group Chemical group 0.000 claims description 2
- 150000002367 halogens Chemical group 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 claims 1
- 150000002440 hydroxy compounds Chemical class 0.000 claims 1
- 230000000749 insecticidal effect Effects 0.000 abstract description 3
- 150000002825 nitriles Chemical class 0.000 abstract description 2
- 125000005843 halogen group Chemical group 0.000 abstract 2
- 125000003342 alkenyl group Chemical group 0.000 abstract 1
- 125000000304 alkynyl group Chemical group 0.000 abstract 1
- 229940092714 benzenesulfonic acid Drugs 0.000 abstract 1
- 229940112021 centrally acting muscle relaxants carbamic acid ester Drugs 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- 125000000532 dioxanyl group Chemical group 0.000 abstract 1
- 150000002431 hydrogen Chemical group 0.000 abstract 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 21
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 239000002253 acid Substances 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 239000003795 chemical substances by application Substances 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- 241000254173 Coleoptera Species 0.000 description 5
- 239000003921 oil Substances 0.000 description 5
- 241001465754 Metazoa Species 0.000 description 4
- 239000003085 diluting agent Substances 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 239000002689 soil Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 241001124076 Aphididae Species 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 125000002877 alkyl aryl group Chemical group 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 239000012141 concentrate Substances 0.000 description 3
- 230000006378 damage Effects 0.000 description 3
- 229930195733 hydrocarbon Natural products 0.000 description 3
- 150000002430 hydrocarbons Chemical class 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 229920000151 polyglycol Polymers 0.000 description 3
- 239000010695 polyglycol Substances 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 239000004563 wettable powder Substances 0.000 description 3
- 241000238876 Acari Species 0.000 description 2
- 239000005995 Aluminium silicate Substances 0.000 description 2
- 241000239290 Araneae Species 0.000 description 2
- 241001674044 Blattodea Species 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- 241000196324 Embryophyta Species 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 239000004606 Fillers/Extenders Substances 0.000 description 2
- 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 2
- 241000256602 Isoptera Species 0.000 description 2
- 241000257159 Musca domestica Species 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 241001491877 Operophtera brumata Species 0.000 description 2
- 241001608568 Phaedon Species 0.000 description 2
- 244000046052 Phaseolus vulgaris Species 0.000 description 2
- 241001510236 Rhyparobia maderae Species 0.000 description 2
- 235000012211 aluminium silicate Nutrition 0.000 description 2
- 235000014121 butter Nutrition 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 239000004927 clay Substances 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 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 2
- 239000011707 mineral Substances 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- KPZGRMZPZLOPBS-UHFFFAOYSA-N 1,3-dichloro-2,2-bis(chloromethyl)propane Chemical compound ClCC(CCl)(CCl)CCl KPZGRMZPZLOPBS-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- PUAQLLVFLMYYJJ-UHFFFAOYSA-N 2-aminopropiophenone Chemical compound CC(N)C(=O)C1=CC=CC=C1 PUAQLLVFLMYYJJ-UHFFFAOYSA-N 0.000 description 1
- ZNCUUYCDKVNVJH-UHFFFAOYSA-N 2-isopropoxyphenol Chemical compound CC(C)OC1=CC=CC=C1O ZNCUUYCDKVNVJH-UHFFFAOYSA-N 0.000 description 1
- 241000253994 Acyrthosiphon pisum Species 0.000 description 1
- 241000449794 Alabama argillacea Species 0.000 description 1
- 102000009027 Albumins Human genes 0.000 description 1
- 108010088751 Albumins Proteins 0.000 description 1
- 244000144730 Amygdalus persica Species 0.000 description 1
- 241001425390 Aphis fabae Species 0.000 description 1
- 241000899771 Arenga undulatifolia Species 0.000 description 1
- 241001166626 Aulacorthum solani Species 0.000 description 1
- 102100027522 Baculoviral IAP repeat-containing protein 7 Human genes 0.000 description 1
- 101710177963 Baculoviral IAP repeat-containing protein 7 Proteins 0.000 description 1
- 241000238805 Blaberus Species 0.000 description 1
- 241000238662 Blatta orientalis Species 0.000 description 1
- 241000256593 Brachycaudus schwartzi Species 0.000 description 1
- 240000007124 Brassica oleracea Species 0.000 description 1
- 241000422252 Cales Species 0.000 description 1
- 240000004385 Centaurea cyanus Species 0.000 description 1
- 235000005940 Centaurea cyanus Nutrition 0.000 description 1
- 241000255579 Ceratitis capitata Species 0.000 description 1
- 241000861718 Chloris <Aves> Species 0.000 description 1
- 241001327638 Cimex lectularius Species 0.000 description 1
- 241001415288 Coccidae Species 0.000 description 1
- 241001465977 Coccoidea Species 0.000 description 1
- 241000289763 Dasygaster padockina Species 0.000 description 1
- 241001513837 Dermestes maculatus Species 0.000 description 1
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 1
- 101100536354 Drosophila melanogaster tant gene Proteins 0.000 description 1
- 241001425472 Dysdercus cingulatus Species 0.000 description 1
- 241000371383 Fannia Species 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 1
- 241000257303 Hymenoptera Species 0.000 description 1
- 241000088861 Latua Species 0.000 description 1
- 241000258916 Leptinotarsa decemlineata Species 0.000 description 1
- 241000254099 Melolontha melolontha Species 0.000 description 1
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 1
- 241001477931 Mythimna unipuncta Species 0.000 description 1
- 241000238887 Ornithodoros Species 0.000 description 1
- 241000131101 Oryzaephilus surinamensis Species 0.000 description 1
- 241000488583 Panonychus ulmi Species 0.000 description 1
- 241001548358 Parapiesma quadratum Species 0.000 description 1
- 241000219833 Phaseolus Species 0.000 description 1
- 235000010627 Phaseolus vulgaris Nutrition 0.000 description 1
- 241000257149 Phormia Species 0.000 description 1
- 241000255972 Pieris <butterfly> Species 0.000 description 1
- 241000690748 Piesma Species 0.000 description 1
- 241000500439 Plutella Species 0.000 description 1
- 241000952063 Polyphagotarsonemus latus Species 0.000 description 1
- 241001290151 Prunus avium subsp. avium Species 0.000 description 1
- 235000006040 Prunus persica var persica Nutrition 0.000 description 1
- 241000586426 Pseudaulacaspis eugeniae Species 0.000 description 1
- 241000722238 Pseudococcus maritimus Species 0.000 description 1
- 206010037660 Pyrexia Diseases 0.000 description 1
- 101100014660 Rattus norvegicus Gimap8 gene Proteins 0.000 description 1
- 241000125167 Rhopalosiphum padi Species 0.000 description 1
- 235000001537 Ribes X gardonianum Nutrition 0.000 description 1
- 235000001535 Ribes X utile Nutrition 0.000 description 1
- 240000001890 Ribes hudsonianum Species 0.000 description 1
- 235000016954 Ribes hudsonianum Nutrition 0.000 description 1
- 235000001466 Ribes nigrum Nutrition 0.000 description 1
- 235000016919 Ribes petraeum Nutrition 0.000 description 1
- 244000281247 Ribes rubrum Species 0.000 description 1
- 235000002355 Ribes spicatum Nutrition 0.000 description 1
- 235000011034 Rubus glaucus Nutrition 0.000 description 1
- 244000235659 Rubus idaeus Species 0.000 description 1
- 235000009122 Rubus idaeus Nutrition 0.000 description 1
- 241001177161 Stegobium paniceum Species 0.000 description 1
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 1
- 241000254109 Tenebrio molitor Species 0.000 description 1
- 241001454295 Tetranychidae Species 0.000 description 1
- 241001414989 Thysanoptera Species 0.000 description 1
- 241000254113 Tribolium castaneum Species 0.000 description 1
- 241000607479 Yersinia pestis Species 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical compound [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 229960000892 attapulgite Drugs 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- PVXRCPDNJSFYBV-UHFFFAOYSA-N carbamoyl fluoride Chemical compound NC(F)=O PVXRCPDNJSFYBV-UHFFFAOYSA-N 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-N carbonic acid monoamide Natural products NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 1
- 235000019693 cherries Nutrition 0.000 description 1
- 125000002603 chloroethyl group Chemical group [H]C([*])([H])C([H])([H])Cl 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- GUJOJGAPFQRJSV-UHFFFAOYSA-N dialuminum;dioxosilane;oxygen(2-);hydrate Chemical compound O.[O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O GUJOJGAPFQRJSV-UHFFFAOYSA-N 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 229960001760 dimethyl sulfoxide Drugs 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 229910000040 hydrogen fluoride Inorganic materials 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- AFCCDDWKHLHPDF-UHFFFAOYSA-M metam-sodium Chemical compound [Na+].CNC([S-])=S AFCCDDWKHLHPDF-UHFFFAOYSA-M 0.000 description 1
- MGJXBDMLVWIYOQ-UHFFFAOYSA-N methylazanide Chemical compound [NH-]C MGJXBDMLVWIYOQ-UHFFFAOYSA-N 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 229910052901 montmorillonite Inorganic materials 0.000 description 1
- LQBJJHHESGHBDW-UHFFFAOYSA-N n-(1,3-dithiolan-2-ylidene)hydroxylamine Chemical compound ON=C1SCCS1 LQBJJHHESGHBDW-UHFFFAOYSA-N 0.000 description 1
- 150000007530 organic bases Chemical group 0.000 description 1
- 150000002923 oximes Chemical class 0.000 description 1
- 229910052625 palygorskite Inorganic materials 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- HCTVWSOKIJULET-LQDWTQKMSA-M phenoxymethylpenicillin potassium Chemical compound [K+].N([C@H]1[C@H]2SC([C@@H](N2C1=O)C([O-])=O)(C)C)C(=O)COC1=CC=CC=C1 HCTVWSOKIJULET-LQDWTQKMSA-M 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- IOVGROKTTNBUGK-SJCJKPOMSA-N ritodrine Chemical compound N([C@@H](C)[C@H](O)C=1C=CC(O)=CC=1)CCC1=CC=C(O)C=C1 IOVGROKTTNBUGK-SJCJKPOMSA-N 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 1
- 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 1
- JFALSRSLKYAFGM-UHFFFAOYSA-N uranium(0) Chemical compound [U] JFALSRSLKYAFGM-UHFFFAOYSA-N 0.000 description 1
- 239000000052 vinegar Substances 0.000 description 1
- 235000021419 vinegar Nutrition 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
Classifications
-
- 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
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
- A01N47/24—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing the groups, or; Thio analogues thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
- C07D317/14—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D317/18—Radicals substituted by singly bound oxygen or sulfur atoms
- C07D317/24—Radicals substituted by singly bound oxygen or sulfur atoms esterified
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
- C07D317/62—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to atoms of the carbocyclic ring
- C07D317/64—Oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D339/00—Heterocyclic compounds containing rings having two sulfur atoms as the only ring hetero atoms
- C07D339/02—Five-membered rings
- C07D339/06—Five-membered rings having the hetero atoms in positions 1 and 3, e.g. cyclic dithiocarbonates
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Agronomy & Crop Science (AREA)
- General Health & Medical Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2254359A DE2254359A1 (de) | 1972-11-07 | 1972-11-07 | N-sulfenylierte carbamate, verfahren zu ihrer herstellung und ihre verwendung als insektizide und akarizide |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1039294A true CA1039294A (en) | 1978-09-26 |
Family
ID=5861006
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA185,112A Expired CA1039294A (en) | 1972-11-07 | 1973-11-06 | N-sulphenylated carbamates and their use as insecticides and acaricides |
Country Status (28)
| Country | Link |
|---|---|
| US (1) | US3954836A (en, 2012) |
| JP (1) | JPS5647164B2 (en, 2012) |
| AT (1) | AT328794B (en, 2012) |
| AU (1) | AU473716B2 (en, 2012) |
| BE (1) | BE806966A (en, 2012) |
| BR (1) | BR7308639D0 (en, 2012) |
| CA (1) | CA1039294A (en, 2012) |
| CH (1) | CH588455A5 (en, 2012) |
| CS (1) | CS172269B2 (en, 2012) |
| DD (1) | DD108641A5 (en, 2012) |
| DE (1) | DE2254359A1 (en, 2012) |
| DK (1) | DK133374C (en, 2012) |
| EG (1) | EG11150A (en, 2012) |
| ES (1) | ES420292A1 (en, 2012) |
| FR (1) | FR2205507B1 (en, 2012) |
| GB (1) | GB1403170A (en, 2012) |
| HU (1) | HU167708B (en, 2012) |
| IE (1) | IE38493B1 (en, 2012) |
| IL (1) | IL43548A (en, 2012) |
| IT (1) | IT1048153B (en, 2012) |
| KE (1) | KE2897A (en, 2012) |
| LU (1) | LU68743A1 (en, 2012) |
| MY (1) | MY7800476A (en, 2012) |
| NL (1) | NL7315120A (en, 2012) |
| PL (1) | PL86963B1 (en, 2012) |
| SU (1) | SU668563A3 (en, 2012) |
| TR (1) | TR17915A (en, 2012) |
| ZA (1) | ZA738516B (en, 2012) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2434184A1 (de) | 1974-07-16 | 1976-02-05 | Bayer Ag | N-sulfenylierte carbamate, verfahren zu ihrer herstellung und verwendung als pesticide |
| US4315928A (en) * | 1975-06-26 | 1982-02-16 | Union Carbide Corporation | N-Aminosulfenyl carbamate compounds, compositions and use |
| IN145063B (en, 2012) * | 1975-12-01 | 1978-08-19 | Union Carbide Corp | |
| US4479002A (en) * | 1975-12-01 | 1984-10-23 | Union Carbide Corporation | Carbamate-carbamoyl fluoride compounds |
| SE7612479L (sv) * | 1975-12-01 | 1977-06-02 | Union Carbide Corp | Karbamatsilfenylkarbamoylfluoridforeningar |
| DE2600981A1 (de) * | 1976-01-13 | 1977-07-21 | Bayer Ag | N-sulfenylierte carbamate, verfahren zu ihrer herstellung sowie ihre verwendung als schaedlingsbekaempfungsmittel |
| US4066689A (en) * | 1976-05-20 | 1978-01-03 | Union Carbide Corporation | Ketoalkanesulfenylcarbamoyl and ketoalkanethiosulfenylcarbamoyl halides |
| US4246283A (en) * | 1976-06-04 | 1981-01-20 | Ciba-Geigy Corporation | Pesticidally active 1-phenyl-1,3,5-triaza-4-sulfa-5-alkylsulfonyl and -phenylsulfonyl-pent-1-en derivatives |
| US4169894A (en) * | 1977-03-28 | 1979-10-02 | Union Carbide Corporation | Pesticidal unsymmetrical n-substituted bis-carbamoyloxy disulfide compounds |
| EP0007398A1 (de) * | 1978-06-08 | 1980-02-06 | F. HOFFMANN-LA ROCHE & CO. Aktiengesellschaft | Thio-methylcarbamat-derivat, Verfahren zu seiner Herstellung, seine Verwendung und Pesticide, die es enthalten |
| JPS5892655A (ja) * | 1981-11-27 | 1983-06-02 | Otsuka Chem Co Ltd | カ−バメイト系誘導体、その製造方法及びその誘導体を有効成分として含有する殺虫剤 |
| US4877901A (en) * | 1988-10-28 | 1989-10-31 | The Goodyear Tire & Rubber Company | Process for synthesizing N,N'-dithiobis(sulfonamides) |
| US4992583A (en) * | 1989-01-06 | 1991-02-12 | The Goodyear Tire & Rubber Company | Process for synthesizing N-chlorothio-sulfonamides |
| US20040094235A1 (en) * | 2002-11-18 | 2004-05-20 | Ge Betz, Inc. | Chrome free treatment for aluminum |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3084096A (en) * | 1955-08-29 | 1963-04-02 | Union Carbide Corp | Indanyl n-methyl carbamate |
-
1972
- 1972-11-07 DE DE2254359A patent/DE2254359A1/de not_active Withdrawn
-
1973
- 1973-10-19 US US05/408,253 patent/US3954836A/en not_active Expired - Lifetime
- 1973-10-26 AU AU61911/73A patent/AU473716B2/en not_active Expired
- 1973-11-02 DD DD174437A patent/DD108641A5/xx unknown
- 1973-11-02 IL IL7343548A patent/IL43548A/en unknown
- 1973-11-05 IT IT30931/73A patent/IT1048153B/it active
- 1973-11-05 CH CH1552573A patent/CH588455A5/xx not_active IP Right Cessation
- 1973-11-05 LU LU68743A patent/LU68743A1/xx unknown
- 1973-11-05 NL NL7315120A patent/NL7315120A/xx not_active Application Discontinuation
- 1973-11-05 PL PL1973166333A patent/PL86963B1/pl unknown
- 1973-11-05 EG EG418/73A patent/EG11150A/xx active
- 1973-11-06 DK DK599673A patent/DK133374C/da active
- 1973-11-06 IE IE1995/73A patent/IE38493B1/xx unknown
- 1973-11-06 BR BR8639/73A patent/BR7308639D0/pt unknown
- 1973-11-06 BE BE137448A patent/BE806966A/xx unknown
- 1973-11-06 CS CS7615A patent/CS172269B2/cs unknown
- 1973-11-06 GB GB5137473A patent/GB1403170A/en not_active Expired
- 1973-11-06 SU SU731969714A patent/SU668563A3/ru active
- 1973-11-06 CA CA185,112A patent/CA1039294A/en not_active Expired
- 1973-11-06 TR TR17915A patent/TR17915A/xx unknown
- 1973-11-06 ES ES420292A patent/ES420292A1/es not_active Expired
- 1973-11-06 ZA ZA738516A patent/ZA738516B/xx unknown
- 1973-11-06 HU HUBA2991A patent/HU167708B/hu unknown
- 1973-11-07 JP JP12459573A patent/JPS5647164B2/ja not_active Expired
- 1973-11-07 FR FR737339562A patent/FR2205507B1/fr not_active Expired
- 1973-11-07 AT AT935573A patent/AT328794B/de not_active IP Right Cessation
-
1978
- 1978-11-02 KE KE2897A patent/KE2897A/xx unknown
- 1978-12-31 MY MY1978476A patent/MY7800476A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| TR17915A (tr) | 1976-11-01 |
| GB1403170A (en) | 1975-08-13 |
| ES420292A1 (es) | 1976-03-01 |
| IL43548A0 (en) | 1974-03-14 |
| CS172269B2 (en, 2012) | 1976-12-29 |
| US3954836A (en) | 1976-05-04 |
| IE38493B1 (en) | 1978-03-29 |
| IE38493L (en) | 1974-05-07 |
| BR7308639D0 (pt) | 1974-08-15 |
| ZA738516B (en) | 1974-09-25 |
| EG11150A (en) | 1977-08-15 |
| IL43548A (en) | 1977-02-28 |
| SU668563A3 (ru) | 1979-06-15 |
| IT1048153B (it) | 1980-11-20 |
| DD108641A5 (de) | 1974-10-05 |
| ATA935573A (de) | 1975-06-15 |
| DK133374B (da) | 1976-05-10 |
| FR2205507A1 (fr) | 1974-05-31 |
| FR2205507B1 (fr) | 1977-05-27 |
| HU167708B (en, 2012) | 1975-12-25 |
| DE2254359A1 (de) | 1974-05-16 |
| AU473716B2 (en) | 1976-07-01 |
| DK133374C (da) | 1976-11-08 |
| CH588455A5 (en, 2012) | 1977-06-15 |
| LU68743A1 (de) | 1974-01-18 |
| JPS50111233A (en, 2012) | 1975-09-01 |
| BE806966A (fr) | 1974-05-06 |
| AT328794B (de) | 1976-04-12 |
| PL86963B1 (en, 2012) | 1976-06-30 |
| KE2897A (en) | 1978-11-17 |
| AU6191173A (en) | 1975-05-01 |
| JPS5647164B2 (en, 2012) | 1981-11-07 |
| NL7315120A (en, 2012) | 1974-05-09 |
| MY7800476A (en) | 1978-12-31 |
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