CA1064945A - Composes symetriques de type bis-carbamate - Google Patents

Composes symetriques de type bis-carbamate

Info

Publication number: CA1064945A
Authority: CA; Canada
Prior art keywords: bis; sulfide; alkyl; plants; test
Prior art date: 1975-12-01
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

CA316,047A

Other languages

English (en)

Inventor

Themistocles D.J. D'silva

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.)

Union Carbide Corp

Original Assignee

Union Carbide Corp

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.)

1975-12-01

Filing date

1978-11-09

Publication date

1979-10-23

1975-12-01 Priority claimed from US05/636,373 external-priority patent/US4382957A/en

1978-11-09 Application filed by Union Carbide Corp filed Critical Union Carbide Corp

1978-11-09 Priority to CA316,047A priority Critical patent/CA1064945A/fr

1979-10-23 Application granted granted Critical

1979-10-23 Publication of CA1064945A publication Critical patent/CA1064945A/fr

Status Expired legal-status Critical Current

Links

150000001875 compounds Chemical class 0.000 claims description 53
-1 alkylthiol alkoxy Chemical group 0.000 claims description 15
125000000217 alkyl group Chemical group 0.000 claims description 13
238000000034 method Methods 0.000 claims description 13
125000004414 alkyl thio group Chemical group 0.000 claims description 9
229910052739 hydrogen Inorganic materials 0.000 claims description 7
239000001257 hydrogen Substances 0.000 claims description 7
239000002253 acid Substances 0.000 claims description 5
125000003545 alkoxy group Chemical group 0.000 claims description 4
125000004093 cyano group Chemical group *C#N 0.000 claims description 4
125000004432 carbon atom Chemical group C* 0.000 claims description 3
PXJJSXABGXMUSU-UHFFFAOYSA-N disulfur dichloride Chemical compound ClSSCl PXJJSXABGXMUSU-UHFFFAOYSA-N 0.000 claims description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
125000001931 aliphatic group Chemical group 0.000 claims description 2
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
125000003282 alkyl amino group Chemical group 0.000 claims description 2
125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 2
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
125000001589 carboacyl group Chemical group 0.000 claims description 2
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 2
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
229910052760 oxygen Inorganic materials 0.000 claims description 2
239000001301 oxygen Substances 0.000 claims description 2
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
229910052717 sulfur Inorganic materials 0.000 claims description 2
239000011593 sulfur Substances 0.000 claims description 2
150000002431 hydrogen Chemical group 0.000 claims 2
125000004644 alkyl sulfinyl group Chemical group 0.000 claims 1
125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims 1
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 1
230000000361 pesticidal effect Effects 0.000 abstract description 8
DQIGGFPVKGZBQQ-UHFFFAOYSA-N s-carbamoyl carbamothioate Chemical class NC(=O)SC(N)=O DQIGGFPVKGZBQQ-UHFFFAOYSA-N 0.000 abstract description 5
231100000674 Phytotoxicity Toxicity 0.000 abstract description 4
231100001225 mammalian toxicity Toxicity 0.000 abstract description 3
238000012360 testing method Methods 0.000 description 48
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 42
229910052757 nitrogen Inorganic materials 0.000 description 32
241000196324 Embryophyta Species 0.000 description 31
UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 30
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 24
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 20
239000000725 suspension Substances 0.000 description 16
239000007787 solid Substances 0.000 description 14
239000000243 solution Substances 0.000 description 14
239000000203 mixture Substances 0.000 description 13
125000005646 oximino group Chemical group 0.000 description 13
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
238000002360 preparation method Methods 0.000 description 11
241000238631 Hexapoda Species 0.000 description 10
150000002923 oximes Chemical class 0.000 description 10
239000007921 spray Substances 0.000 description 10
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
238000006243 chemical reaction Methods 0.000 description 8
239000003995 emulsifying agent Substances 0.000 description 8
238000009472 formulation Methods 0.000 description 8
238000003756 stirring Methods 0.000 description 8
231100000167 toxic agent Toxicity 0.000 description 8
239000003440 toxic substance Substances 0.000 description 8
229940086542 triethylamine Drugs 0.000 description 8
241001124076 Aphididae Species 0.000 description 7
239000000047 product Substances 0.000 description 7
IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 6
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
239000011541 reaction mixture Substances 0.000 description 6
241000712024 Brassica rapa var. perviridis Species 0.000 description 5
238000007865 diluting Methods 0.000 description 5
239000002270 dispersing agent Substances 0.000 description 5
239000013020 final formulation Substances 0.000 description 5
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
241000244206 Nematoda Species 0.000 description 4
241001521235 Spodoptera eridania Species 0.000 description 4
241000607479 Yersinia pestis Species 0.000 description 4
239000003795 chemical substances by application Substances 0.000 description 4
239000003085 diluting agent Substances 0.000 description 4
230000000694 effects Effects 0.000 description 4
235000013305 food Nutrition 0.000 description 4
WSFSSNUMVMOOMR-UHFFFAOYSA-N formaldehyde Substances O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 4
239000007788 liquid Substances 0.000 description 4
239000002689 soil Substances 0.000 description 4
241000238876 Acari Species 0.000 description 3
241001425390 Aphis fabae Species 0.000 description 3
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
241000462639 Epilachna varivestis Species 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
208000027418 Wounds and injury Diseases 0.000 description 3
230000006378 damage Effects 0.000 description 3
125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
239000012442 inert solvent Substances 0.000 description 3
208000014674 injury Diseases 0.000 description 3
230000033001 locomotion Effects 0.000 description 3
229910052943 magnesium sulfate Inorganic materials 0.000 description 3
235000019341 magnesium sulphate Nutrition 0.000 description 3
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
230000000638 stimulation Effects 0.000 description 3
238000012546 transfer Methods 0.000 description 3
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
240000008067 Cucumis sativus Species 0.000 description 2
235000010799 Cucumis sativus var sativus Nutrition 0.000 description 2
241000255925 Diptera Species 0.000 description 2
241001465754 Metazoa Species 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
239000004480 active ingredient Substances 0.000 description 2
239000000969 carrier Substances 0.000 description 2
239000004927 clay Substances 0.000 description 2
238000007796 conventional method Methods 0.000 description 2
238000000354 decomposition reaction Methods 0.000 description 2
239000012895 dilution Substances 0.000 description 2
238000010790 dilution Methods 0.000 description 2
239000006185 dispersion Substances 0.000 description 2
230000001804 emulsifying effect Effects 0.000 description 2
229940093499 ethyl acetate Drugs 0.000 description 2
235000019439 ethyl acetate Nutrition 0.000 description 2
238000002474 experimental method Methods 0.000 description 2
230000007062 hydrolysis Effects 0.000 description 2
238000006460 hydrolysis reaction Methods 0.000 description 2
150000007529 inorganic bases Chemical class 0.000 description 2
150000002500 ions Chemical class 0.000 description 2
235000014666 liquid concentrate Nutrition 0.000 description 2
229960000965 nimesulide Drugs 0.000 description 2
239000000376 reactant Substances 0.000 description 2
HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 2
239000002904 solvent Substances 0.000 description 2
239000000126 substance Substances 0.000 description 2
OWFJMIVZYSDULZ-PXOLEDIWSA-N (4s,4ar,5s,5ar,6s,12ar)-4-(dimethylamino)-1,5,6,10,11,12a-hexahydroxy-6-methyl-3,12-dioxo-4,4a,5,5a-tetrahydrotetracene-2-carboxamide Chemical compound C1=CC=C2[C@](O)(C)[C@H]3[C@H](O)[C@H]4[C@H](N(C)C)C(=O)C(C(N)=O)=C(O)[C@@]4(O)C(=O)C3=C(O)C2=C1O OWFJMIVZYSDULZ-PXOLEDIWSA-N 0.000 description 1
NCNSBFDGXBKAKB-UHFFFAOYSA-N (methylsulfanyl)acetaldehyde Chemical compound CSCC=O NCNSBFDGXBKAKB-UHFFFAOYSA-N 0.000 description 1
IFDZZSXEPSSHNC-ONEGZZNKSA-N (ne)-n-propylidenehydroxylamine Chemical compound CC\C=N\O IFDZZSXEPSSHNC-ONEGZZNKSA-N 0.000 description 1
IGOWHGRNPLFNDJ-ZPHPHTNESA-N (z)-9-tricosene Chemical compound CCCCCCCCCCCCC\C=C/CCCCCCCC IGOWHGRNPLFNDJ-ZPHPHTNESA-N 0.000 description 1
IMLSAISZLJGWPP-UHFFFAOYSA-N 1,3-dithiolane Chemical compound C1CSCS1 IMLSAISZLJGWPP-UHFFFAOYSA-N 0.000 description 1
KRDLVBAPHAYKSP-UHFFFAOYSA-N 2-cyanoethyl n-hydroxyethanimidothioate Chemical compound ON=C(C)SCCC#N KRDLVBAPHAYKSP-UHFFFAOYSA-N 0.000 description 1
NXZLTPQEYLXQCH-UHFFFAOYSA-N 2-hydroxyiminoacetamide Chemical compound NC(=O)C=NO NXZLTPQEYLXQCH-UHFFFAOYSA-N 0.000 description 1
241000239223 Arachnida Species 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
241000254173 Coleoptera Species 0.000 description 1
241000784713 Cupido Species 0.000 description 1
KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-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
239000005909 Kieselgur Substances 0.000 description 1
STECJAGHUSJQJN-USLFZFAMSA-N LSM-4015 Chemical compound C1([C@@H](CO)C(=O)OC2C[C@@H]3N([C@H](C2)[C@@H]2[C@H]3O2)C)=CC=CC=C1 STECJAGHUSJQJN-USLFZFAMSA-N 0.000 description 1
241000124008 Mammalia Species 0.000 description 1
241001024304 Mino Species 0.000 description 1
241000257159 Musca domestica Species 0.000 description 1
241000257226 Muscidae Species 0.000 description 1
241001325209 Nama Species 0.000 description 1
241000849798 Nita Species 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
244000046052 Phaseolus vulgaris Species 0.000 description 1
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
239000004743 Polypropylene Substances 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
240000001260 Tropaeolum majus Species 0.000 description 1
239000002250 absorbent Substances 0.000 description 1
230000002745 absorbent Effects 0.000 description 1
239000000642 acaricide Substances 0.000 description 1
RAFKCLFWELPONH-UHFFFAOYSA-N acetonitrile;dichloromethane Chemical compound CC#N.ClCCl RAFKCLFWELPONH-UHFFFAOYSA-N 0.000 description 1
239000013543 active substance Substances 0.000 description 1
125000000129 anionic group Chemical group 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
239000003849 aromatic solvent Substances 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
239000000440 bentonite Substances 0.000 description 1
229910000278 bentonite Inorganic materials 0.000 description 1
SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
150000004657 carbamic acid derivatives Chemical class 0.000 description 1
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
239000001569 carbon dioxide Substances 0.000 description 1
229910002092 carbon dioxide Inorganic materials 0.000 description 1
125000002091 cationic group Chemical group 0.000 description 1
229910052570 clay Inorganic materials 0.000 description 1
239000000470 constituent Substances 0.000 description 1
150000003983 crown ethers Chemical class 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
125000004966 cyanoalkyl group Chemical group 0.000 description 1
QAWTYRYXDYHQNU-UHFFFAOYSA-N diazathiane Chemical compound NSN QAWTYRYXDYHQNU-UHFFFAOYSA-N 0.000 description 1
239000000428 dust Substances 0.000 description 1
235000013601 eggs Nutrition 0.000 description 1
WSPSLJLXRDCXKO-UHFFFAOYSA-N ethyl 2-methylsulfanyl-2-oxoacetate Chemical compound CSC(=O)C(=O)OCC WSPSLJLXRDCXKO-UHFFFAOYSA-N 0.000 description 1
WDCDAAMJNUHOIY-UHFFFAOYSA-N ethyl acetate;2-propan-2-yloxypropane Chemical compound CCOC(C)=O.CC(C)OC(C)C WDCDAAMJNUHOIY-UHFFFAOYSA-N 0.000 description 1
229940035423 ethyl ether Drugs 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
238000001914 filtration Methods 0.000 description 1
239000008187 granular material Substances 0.000 description 1
229910000040 hydrogen fluoride Inorganic materials 0.000 description 1
125000001841 imino group Chemical group [H]N=* 0.000 description 1
239000002054 inoculum Substances 0.000 description 1
239000002917 insecticide Substances 0.000 description 1
230000001418 larval effect Effects 0.000 description 1
239000010410 layer Substances 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
239000000463 material Substances 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
HAMGRBXTJNITHG-UHFFFAOYSA-N methyl isocyanate Chemical compound CN=C=O HAMGRBXTJNITHG-UHFFFAOYSA-N 0.000 description 1
230000001617 migratory effect Effects 0.000 description 1
GLMUAFMGXXHGLU-VQAITOIOSA-N minocycline hydrochloride Chemical group [H+].[Cl-].C([C@H]1C2)C3=C(N(C)C)C=CC(O)=C3C(=O)C1=C(O)[C@@]1(O)[C@@H]2[C@H](N(C)C)C(O)=C(C(N)=O)C1=O GLMUAFMGXXHGLU-VQAITOIOSA-N 0.000 description 1
JPSHMDUAFDEKAR-UHFFFAOYSA-N n-(1,4-dithian-2-ylidene)hydroxylamine Chemical compound ON=C1CSCCS1 JPSHMDUAFDEKAR-UHFFFAOYSA-N 0.000 description 1
230000001069 nematicidal effect Effects 0.000 description 1
239000005645 nematicide Substances 0.000 description 1
HYWYRSMBCFDLJT-UHFFFAOYSA-N nimesulide Chemical compound CS(=O)(=O)NC1=CC=C([N+]([O-])=O)C=C1OC1=CC=CC=C1 HYWYRSMBCFDLJT-UHFFFAOYSA-N 0.000 description 1
238000005580 one pot reaction Methods 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
239000012044 organic layer Substances 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
239000000575 pesticide Substances 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
235000009048 phenolic acids Nutrition 0.000 description 1
229920001155 polypropylene Polymers 0.000 description 1
239000000843 powder Substances 0.000 description 1
OVARTBFNCCXQKS-UHFFFAOYSA-N propan-2-one;hydrate Chemical compound O.CC(C)=O OVARTBFNCCXQKS-UHFFFAOYSA-N 0.000 description 1
150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
150000003242 quaternary ammonium salts Chemical class 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
238000012216 screening Methods 0.000 description 1
241000894007 species Species 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
230000002269 spontaneous effect Effects 0.000 description 1
238000005507 spraying Methods 0.000 description 1
238000010561 standard procedure Methods 0.000 description 1
125000004646 sulfenyl group Chemical group S(*)* 0.000 description 1
FWMUJAIKEJWSSY-UHFFFAOYSA-N sulfur dichloride Chemical compound ClSCl FWMUJAIKEJWSSY-UHFFFAOYSA-N 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
238000010998 test method Methods 0.000 description 1
239000012085 test solution Substances 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
238000009966 trimming Methods 0.000 description 1
239000004563 wettable powder Substances 0.000 description 1
229940001158 ximino Drugs 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Landscapes

Agricultural Chemicals And Associated Chemicals (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

CA316,047A 1975-12-01 1978-11-09 Composes symetriques de type bis-carbamate Expired CA1064945A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA316,047A CA1064945A (fr)	1975-12-01	1978-11-09	Composes symetriques de type bis-carbamate

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
US05/636,373 US4382957A (en)	1975-12-01	1975-12-01	Symmetrical insecticidal bis-carbamate compounds
CA265,685A CA1062271A (fr)	1975-12-01	1976-11-15	Composes symetriques de type bis-carbamate
CA316,047A CA1064945A (fr)	1975-12-01	1978-11-09	Composes symetriques de type bis-carbamate

Publications (1)

Publication Number	Publication Date
CA1064945A true CA1064945A (fr)	1979-10-23

Family

ID=27164769

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA316,047A Expired CA1064945A (fr)	1975-12-01	1978-11-09	Composes symetriques de type bis-carbamate

Country Status (1)

Country	Link
CA (1)	CA1064945A (fr)

1978
- 1978-11-09 CA CA316,047A patent/CA1064945A/fr not_active Expired

Publication	Publication Date	Title
US3217037A (en)	1965-11-09	2-hydrocarbylthio-sulfinyl and sulfonylalkanal carbamoyloximes
CA1062271A (fr)	1979-09-11	Composes symetriques de type bis-carbamate
US4341795A (en)	1982-07-27	Asymmetrical bis-carbamate compounds
US3299137A (en)	1967-01-17	Acyclic hydrocarbon aldehyde carbamoyl oximes
CA1110647A (fr)	1981-10-13	Composes a base de sulfure de bis-carbamoyles n- substitues
US3400153A (en)	1968-09-03	Nitroalkyl carbamoyloximes
US4029688A (en)	1977-06-14	Carbamic pesticidal compositions
CA1058627A (fr)	1979-07-17	Pesticides a base de carbamate
CA1069127A (fr)	1980-01-01	Composes de type fluorure de carbamate-sulfenyle-carbamoyle
US4327110A (en)	1982-04-27	Pesticidal symmetrical N-substituted bis-carbamoyloximino disulfide compounds
US4181734A (en)	1980-01-01	Pesticidal N-[2,2-dimethyl-2,3-dihydro-7-benzofuranyl-methyl-carbamate]N-[4-] sulfide
US4166864A (en)	1979-09-04	Pesticidal unsymmetrical bis-arylcarbamate disulfide compounds
US4315928A (en)	1982-02-16	N-Aminosulfenyl carbamate compounds, compositions and use
US3507965A (en)	1970-04-21	Insecticidal and miticidal methods and compositions of carbamate derivatives of 2-alkyl-thio(or oxy)alkanaldoximes
CA1064945A (fr)	1979-10-23	Composes symetriques de type bis-carbamate
US3930002A (en)	1975-12-30	Carbamate pesticidal compositions
US4169894A (en)	1979-10-02	Pesticidal unsymmetrical n-substituted bis-carbamoyloxy disulfide compounds
US4122204A (en)	1978-10-24	N-(4-tert-butylphenylthiosulfenyl)-N-alkyl aryl carbamate compounds
US3894150A (en)	1975-07-08	Carbamate pesticidal compositions
CA1087621A (fr)	1980-10-14	Produits a base de thiosulfenylcarbamoylfluorure de carbamate
US4124721A (en)	1978-11-07	Pesticidal unsymmetrical bis-arylcarbamate sulfide compounds containing a 2,3, dehyrobenzofuran group
US4338450A (en)	1982-07-06	Carbamate-sulfenyl-carbamoyl fluoride compounds
US4496721A (en)	1985-01-29	Process for preparing symmetrical bis-carbamates
US4568671A (en)	1986-02-04	Pesticidal oxime N-alkyl-N-α-(alkylthio-phosphorothio)acyl carbamates
US4232035A (en)	1980-11-04	Carbamate pesticidal compounds compositions and methods of use