CA1110656A - Sulfonamides n- [[arylformimidoyl]methylamino]thio]-n- substituees - Google Patents

Sulfonamides n- [[arylformimidoyl]methylamino]thio]-n- substituees

Info

Publication number: CA1110656A
Authority: CA; Canada
Prior art keywords: chloro; thio; methylamino; tolyl; formimidoyl
Prior art date: 1977-06-09
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

CA302,748A

Other languages

English (en)

Inventor

Victor L. Rizzo

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.)

Pharmacia and Upjohn Co

Original Assignee

Upjohn Co

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.)

1977-06-09

Filing date

1978-05-05

Publication date

1981-10-13

1978-05-05 Application filed by Upjohn Co filed Critical Upjohn Co

1981-10-13 Application granted granted Critical

1981-10-13 Publication of CA1110656A publication Critical patent/CA1110656A/fr

Status Expired legal-status Critical Current

Links

125000000446 sulfanediyl group Chemical group *S* 0.000 title claims abstract description 49
125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 title claims abstract description 45
229940124530 sulfonamide Drugs 0.000 title claims abstract description 13
150000003456 sulfonamides Chemical class 0.000 title claims abstract description 11
238000000034 method Methods 0.000 claims abstract description 72
241000607479 Yersinia pestis Species 0.000 claims abstract description 41
241000238876 Acari Species 0.000 claims abstract description 11
241000238631 Hexapoda Species 0.000 claims abstract description 9
150000001875 compounds Chemical class 0.000 claims description 132
-1 N-[[[N-2,4-xylylformimidoyl]methylamino]thio]-N-substituted sulfonamide Chemical class 0.000 claims description 93
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 47
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 39
125000004432 carbon atom Chemical group C* 0.000 claims description 37
125000001309 chloro group Chemical group Cl* 0.000 claims description 36
125000000217 alkyl group Chemical group 0.000 claims description 35
125000001246 bromo group Chemical group Br* 0.000 claims description 34
125000004005 formimidoyl group Chemical group [H]\N=C(/[H])* 0.000 claims description 25
125000001424 substituent group Chemical group 0.000 claims description 15
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 13
125000004093 cyano group Chemical group *C#N 0.000 claims description 9
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 9
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 9
125000003545 alkoxy group Chemical group 0.000 claims description 8
125000000753 cycloalkyl group Chemical group 0.000 claims description 6
241000239223 Arachnida Species 0.000 claims description 4
229910052739 hydrogen Inorganic materials 0.000 claims description 3
239000001257 hydrogen Substances 0.000 claims description 3
XSRMIRRAZGMUFS-UHFFFAOYSA-N n-[2-(2,4-dimethylphenyl)iminoethylamino]sulfanyl-n-phenylmethanesulfonamide Chemical compound CC1=CC(C)=CC=C1N=CCNSN(S(C)(=O)=O)C1=CC=CC=C1 XSRMIRRAZGMUFS-UHFFFAOYSA-N 0.000 claims description 3
DGFSJVOBFNYBJB-UHFFFAOYSA-N n-[2-(5-chloro-2-methylphenyl)iminoethylamino]sulfanyl-n,4-dimethylbenzenesulfonamide Chemical compound C=1C=C(C)C=CC=1S(=O)(=O)N(C)SNCC=NC1=CC(Cl)=CC=C1C DGFSJVOBFNYBJB-UHFFFAOYSA-N 0.000 claims description 3
125000004429 atom Chemical group 0.000 claims description 2
YNZJUYMNFWEQDS-UHFFFAOYSA-N n-[2-(2,4-dimethylphenyl)iminoethylamino]sulfanyl-n-methylmethanesulfonamide Chemical compound CS(=O)(=O)N(C)SNCC=NC1=CC=C(C)C=C1C YNZJUYMNFWEQDS-UHFFFAOYSA-N 0.000 claims description 2
LUAOFLIEWKEFPP-UHFFFAOYSA-N n-cyclohexyl-n-[2-(2,4-dimethylphenyl)iminoethylamino]sulfanylmethanesulfonamide Chemical compound CC1=CC(C)=CC=C1N=CCNSN(S(C)(=O)=O)C1CCCCC1 LUAOFLIEWKEFPP-UHFFFAOYSA-N 0.000 claims description 2
FTUBKGSBCQLJRV-UHFFFAOYSA-N C1=CC(C)=CC=C1S(=O)(=O)N(C=1C=CC(Cl)=CC=1)SNCC=NC1=CC(Cl)=CC=C1C Chemical compound C1=CC(C)=CC=C1S(=O)(=O)N(C=1C=CC(Cl)=CC=1)SNCC=NC1=CC(Cl)=CC=C1C FTUBKGSBCQLJRV-UHFFFAOYSA-N 0.000 claims 2
CTEPQESXPGIPBV-UHFFFAOYSA-N N-(4-chlorophenyl)-N-[2-(2,4-dimethylphenyl)iminoethylamino]sulfanyl-4-methylbenzenesulfonamide Chemical compound C1(=C(C=C(C=C1)C)C)N=CCNSN(S(=O)(=O)C1=CC=C(C=C1)C)C1=CC=C(C=C1)Cl CTEPQESXPGIPBV-UHFFFAOYSA-N 0.000 claims 2
125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
BDJNZSWEQNVWQI-UHFFFAOYSA-N n'-(5-chloro-2-methylphenyl)-n-methyl-n-[(4-methylphenyl)sulfonyl-propan-2-ylamino]sulfanylmethanimidamide Chemical compound C=1C=C(C)C=CC=1S(=O)(=O)N(C(C)C)SN(C)C=NC1=CC(Cl)=CC=C1C BDJNZSWEQNVWQI-UHFFFAOYSA-N 0.000 claims 2
MPGSVXMXCIINBX-UHFFFAOYSA-N n-[2-(5-chloro-2-methylphenyl)iminoethylamino]sulfanyl-1-phenyl-n-propan-2-ylmethanesulfonamide Chemical compound C=1C=CC=CC=1CS(=O)(=O)N(C(C)C)SNCC=NC1=CC(Cl)=CC=C1C MPGSVXMXCIINBX-UHFFFAOYSA-N 0.000 claims 2
VVBYERGMBHXHLI-UHFFFAOYSA-N n-[2-(5-chloro-2-methylphenyl)iminoethylamino]sulfanyl-4-methyl-n-phenylbenzenesulfonamide Chemical compound C1=CC(C)=CC=C1S(=O)(=O)N(C=1C=CC=CC=1)SNCC=NC1=CC(Cl)=CC=C1C VVBYERGMBHXHLI-UHFFFAOYSA-N 0.000 claims 2
CWTSENGCQVYDEJ-UHFFFAOYSA-N n-[2-(5-chloro-2-methylphenyl)iminoethylamino]sulfanyl-n-cyclohexylmethanesulfonamide Chemical compound CC1=CC=C(Cl)C=C1N=CCNSN(S(C)(=O)=O)C1CCCCC1 CWTSENGCQVYDEJ-UHFFFAOYSA-N 0.000 claims 2
KHMUCVSXHUSQNA-UHFFFAOYSA-N n-[2-(5-chloro-2-methylphenyl)iminoethylamino]sulfanyl-n-ethyl-4-methylbenzenesulfonamide Chemical compound C=1C=C(C)C=CC=1S(=O)(=O)N(CC)SNCC=NC1=CC(Cl)=CC=C1C KHMUCVSXHUSQNA-UHFFFAOYSA-N 0.000 claims 2
ZISJQQOTARMALF-UHFFFAOYSA-N n-[2-(5-chloro-2-methylphenyl)iminoethylamino]sulfanyl-n-methylmethanesulfonamide Chemical compound CS(=O)(=O)N(C)SNCC=NC1=CC(Cl)=CC=C1C ZISJQQOTARMALF-UHFFFAOYSA-N 0.000 claims 2
YXZMPVSIFZTJCM-UHFFFAOYSA-N n-[2-(5-chloro-2-methylphenyl)iminoethylamino]sulfanyl-n-phenylmethanesulfonamide Chemical compound CC1=CC=C(Cl)C=C1N=CCNSN(S(C)(=O)=O)C1=CC=CC=C1 YXZMPVSIFZTJCM-UHFFFAOYSA-N 0.000 claims 2
GRIOQQHAQZQLII-UHFFFAOYSA-N n-[2-(5-chloro-2-methylphenyl)iminoethylamino]sulfanyl-n-propan-2-ylbenzenesulfonamide Chemical compound C=1C=CC=CC=1S(=O)(=O)N(C(C)C)SNCC=NC1=CC(Cl)=CC=C1C GRIOQQHAQZQLII-UHFFFAOYSA-N 0.000 claims 2
XGGVVDATVXNSNT-UHFFFAOYSA-N n-benzyl-n-[2-(5-chloro-2-methylphenyl)iminoethylamino]sulfanylmethanesulfonamide Chemical compound CC1=CC=C(Cl)C=C1N=CCNSN(S(C)(=O)=O)CC1=CC=CC=C1 XGGVVDATVXNSNT-UHFFFAOYSA-N 0.000 claims 2
FGNSOIXSMMVXDU-UHFFFAOYSA-N 4-chloro-n-[2-(2,4-dimethylphenyl)iminoethylamino]sulfanyl-n-propan-2-ylbenzenesulfonamide Chemical compound C=1C=C(Cl)C=CC=1S(=O)(=O)N(C(C)C)SNCC=NC1=CC=C(C)C=C1C FGNSOIXSMMVXDU-UHFFFAOYSA-N 0.000 claims 1
HFNHOEIUURCPMZ-UHFFFAOYSA-N n-[2-(5-chloro-2-methylphenyl)iminoethylamino]sulfanyl-n-propan-2-ylmethanesulfonamide Chemical compound CC(C)N(S(C)(=O)=O)SNCC=NC1=CC(Cl)=CC=C1C HFNHOEIUURCPMZ-UHFFFAOYSA-N 0.000 claims 1
QIKKKTOEOHFFAN-UHFFFAOYSA-N n-benzyl-n-[2-(5-chloro-2-methylphenyl)iminoethylamino]sulfanyl-4-methylbenzenesulfonamide Chemical compound C1=CC(C)=CC=C1S(=O)(=O)N(SNCC=NC=1C(=CC=C(Cl)C=1)C)CC1=CC=CC=C1 QIKKKTOEOHFFAN-UHFFFAOYSA-N 0.000 claims 1
ZEMFVPJWKIVOEB-UHFFFAOYSA-N n-tert-butyl-n-[2-(5-chloro-2-methylphenyl)iminoethylamino]sulfanyl-4-methylbenzenesulfonamide Chemical compound C1=CC(C)=CC=C1S(=O)(=O)N(C(C)(C)C)SNCC=NC1=CC(Cl)=CC=C1C ZEMFVPJWKIVOEB-UHFFFAOYSA-N 0.000 claims 1
230000000361 pesticidal effect Effects 0.000 abstract description 11
241000238421 Arthropoda Species 0.000 abstract description 7
239000000047 product Substances 0.000 description 51
239000000203 mixture Substances 0.000 description 40
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 24
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 24
239000013078 crystal Substances 0.000 description 21
239000000243 solution Substances 0.000 description 21
238000004458 analytical method Methods 0.000 description 20
239000002904 solvent Substances 0.000 description 20
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 16
239000000460 chlorine Substances 0.000 description 16
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
NXUHAAIJVABUMJ-UHFFFAOYSA-N 4-methyl-n-propan-2-ylbenzenesulfonamide Chemical compound CC(C)NS(=O)(=O)C1=CC=C(C)C=C1 NXUHAAIJVABUMJ-UHFFFAOYSA-N 0.000 description 12
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
241000196324 Embryophyta Species 0.000 description 12
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 11
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical class CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
239000011541 reaction mixture Substances 0.000 description 10
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 9
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
241001465754 Metazoa Species 0.000 description 9
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
238000006243 chemical reaction Methods 0.000 description 9
229910052801 chlorine Inorganic materials 0.000 description 9
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 9
PNKUSGQVOMIXLU-UHFFFAOYSA-N Formamidine Chemical class NC=N PNKUSGQVOMIXLU-UHFFFAOYSA-N 0.000 description 8
229960004592 isopropanol Drugs 0.000 description 8
239000007921 spray Substances 0.000 description 8
239000002253 acid Substances 0.000 description 7
239000012141 concentrate Substances 0.000 description 7
235000008504 concentrate Nutrition 0.000 description 7
238000009472 formulation Methods 0.000 description 7
JIIOLEGNERQDIP-UHFFFAOYSA-N N'-(2,4-dimethylphenyl)-N-methylformamidine Chemical compound CN=CNC1=CC=C(C)C=C1C JIIOLEGNERQDIP-UHFFFAOYSA-N 0.000 description 6
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 6
235000019441 ethanol Nutrition 0.000 description 6
239000003960 organic solvent Substances 0.000 description 6
YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 6
239000004094 surface-active agent Substances 0.000 description 6
125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 5
239000006185 dispersion Substances 0.000 description 5
239000000839 emulsion Substances 0.000 description 5
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 5
239000007787 solid Substances 0.000 description 5
239000004563 wettable powder Substances 0.000 description 5
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 4
238000005481 NMR spectroscopy Methods 0.000 description 4
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
239000004480 active ingredient Substances 0.000 description 4
229910052799 carbon Inorganic materials 0.000 description 4
239000000969 carrier Substances 0.000 description 4
230000000694 effects Effects 0.000 description 4
239000004495 emulsifiable concentrate Substances 0.000 description 4
125000006178 methyl benzyl group Chemical group 0.000 description 4
GWLOGZRVYXAHRE-UHFFFAOYSA-N n,4-dimethylbenzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=C(C)C=C1 GWLOGZRVYXAHRE-UHFFFAOYSA-N 0.000 description 4
239000003921 oil Substances 0.000 description 4
235000019198 oils Nutrition 0.000 description 4
230000003151 ovacidal effect Effects 0.000 description 4
125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 4
239000002689 soil Substances 0.000 description 4
150000003512 tertiary amines Chemical class 0.000 description 4
125000003944 tolyl group Chemical group 0.000 description 4
229940086542 triethylamine Drugs 0.000 description 4
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
YXVTZEKTVIURPI-UHFFFAOYSA-N 4-methyl-n-[[(4-methylphenyl)sulfonyl-propan-2-ylamino]disulfanyl]-n-propan-2-ylbenzenesulfonamide Chemical compound C=1C=C(C)C=CC=1S(=O)(=O)N(C(C)C)SSN(C(C)C)S(=O)(=O)C1=CC=C(C)C=C1 YXVTZEKTVIURPI-UHFFFAOYSA-N 0.000 description 3
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
239000002250 absorbent Substances 0.000 description 3
230000002745 absorbent Effects 0.000 description 3
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239000003085 diluting agent Substances 0.000 description 3
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235000013399 edible fruits Nutrition 0.000 description 3
235000013305 food Nutrition 0.000 description 3
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UHNHTTIUNATJKL-UHFFFAOYSA-N n-methylmethanesulfonamide Chemical compound CNS(C)(=O)=O UHNHTTIUNATJKL-UHFFFAOYSA-N 0.000 description 3
239000012044 organic layer Substances 0.000 description 3
239000000575 pesticide Substances 0.000 description 3
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125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 3
238000001953 recrystallisation Methods 0.000 description 3
159000000000 sodium salts Chemical class 0.000 description 3
238000005507 spraying Methods 0.000 description 3
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 3
YCMLQMDWSXFTIF-UHFFFAOYSA-N 2-methylbenzenesulfonimidic acid Chemical compound CC1=CC=CC=C1S(N)(=O)=O YCMLQMDWSXFTIF-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
240000002024 Gossypium herbaceum Species 0.000 description 2
235000004341 Gossypium herbaceum Nutrition 0.000 description 2
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IJEIYEJUYJRUSB-UHFFFAOYSA-N N-phenylmethanesulfonamide Chemical compound CS(=O)(=O)NC1=CC=CC=C1.CS(=O)(=O)NC1=CC=CC=C1 IJEIYEJUYJRUSB-UHFFFAOYSA-N 0.000 description 2
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125000002877 alkyl aryl group Chemical group 0.000 description 2
150000008055 alkyl aryl sulfonates Chemical class 0.000 description 2
239000000440 bentonite Substances 0.000 description 2
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SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 2
125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 2
239000011575 calcium Substances 0.000 description 2
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125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
CZZYITDELCSZES-UHFFFAOYSA-N diphenylmethane Chemical group C=1C=CC=CC=1CC1=CC=CC=C1 CZZYITDELCSZES-UHFFFAOYSA-N 0.000 description 2
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BYRVHDUEHUSDDB-UHFFFAOYSA-N n-(3-chloro-4-methylphenyl)-n'-methylmethanimidamide Chemical group CNC=NC1=CC=C(C)C(Cl)=C1 BYRVHDUEHUSDDB-UHFFFAOYSA-N 0.000 description 2
NKRWSSKSSNJQAK-UHFFFAOYSA-N n-(5-chloro-2-methylphenyl)-n'-methylmethanimidamide Chemical compound CNC=NC1=CC(Cl)=CC=C1C NKRWSSKSSNJQAK-UHFFFAOYSA-N 0.000 description 2
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
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239000011734 sodium Substances 0.000 description 2
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FDDDEECHVMSUSB-UHFFFAOYSA-N sulfanilamide Chemical compound NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 description 2
BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 2
125000001273 sulfonato group Chemical class [O-]S(*)(=O)=O 0.000 description 2
FWMUJAIKEJWSSY-UHFFFAOYSA-N sulfur dichloride Chemical compound ClSCl FWMUJAIKEJWSSY-UHFFFAOYSA-N 0.000 description 2
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
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239000008119 colloidal silica Substances 0.000 description 1
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235000012343 cottonseed oil Nutrition 0.000 description 1
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235000014113 dietary fatty acids Nutrition 0.000 description 1
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150000002430 hydrocarbons Chemical class 0.000 description 1
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239000003112 inhibitor Substances 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
239000003350 kerosene Substances 0.000 description 1
229940070765 laurate Drugs 0.000 description 1
230000001665 lethal effect Effects 0.000 description 1
229920005610 lignin Polymers 0.000 description 1
XCOBTUNSZUJCDH-UHFFFAOYSA-B lithium magnesium sodium silicate Chemical compound [Li+].[Li+].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[Na+].[Na+].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].O1[Si](O2)([O-])O[Si]3([O-])O[Si]1([O-])O[Si]2([O-])O3.O1[Si](O2)([O-])O[Si]3([O-])O[Si]1([O-])O[Si]2([O-])O3.O1[Si](O2)([O-])O[Si]3([O-])O[Si]1([O-])O[Si]2([O-])O3.O1[Si](O2)([O-])O[Si]3([O-])O[Si]1([O-])O[Si]2([O-])O3.O1[Si](O2)([O-])O[Si]3([O-])O[Si]1([O-])O[Si]2([O-])O3.O1[Si](O2)([O-])O[Si]3([O-])O[Si]1([O-])O[Si]2([O-])O3 XCOBTUNSZUJCDH-UHFFFAOYSA-B 0.000 description 1
230000005923 long-lasting effect Effects 0.000 description 1
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231100001225 mammalian toxicity Toxicity 0.000 description 1
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238000002844 melting Methods 0.000 description 1
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229920000609 methyl cellulose Polymers 0.000 description 1
229940050176 methyl chloride Drugs 0.000 description 1
239000001923 methylcellulose Substances 0.000 description 1
235000010981 methylcellulose Nutrition 0.000 description 1
238000003801 milling Methods 0.000 description 1
239000003607 modifier Substances 0.000 description 1
229910052901 montmorillonite Inorganic materials 0.000 description 1
QZBAIJIDEKPQSL-UHFFFAOYSA-N n'-chlorobenzenecarboximidamide Chemical compound ClN=C(N)C1=CC=CC=C1 QZBAIJIDEKPQSL-UHFFFAOYSA-N 0.000 description 1
NLLSDZFMWQHOJU-UHFFFAOYSA-N n-(2,4-dichlorophenyl)-n'-methylmethanimidamide Chemical compound CNC=NC1=CC=C(Cl)C=C1Cl NLLSDZFMWQHOJU-UHFFFAOYSA-N 0.000 description 1
WFWIOWHLKROTDB-UHFFFAOYSA-N n-(3-bromo-4-methylphenyl)-n'-methylmethanimidamide Chemical compound CNC=NC1=CC=C(C)C(Br)=C1 WFWIOWHLKROTDB-UHFFFAOYSA-N 0.000 description 1
NQSPHDQXACIRTA-UHFFFAOYSA-N n-(4-chloro-2-ethylphenyl)-n'-methylmethanimidamide Chemical group CCC1=CC(Cl)=CC=C1N=CNC NQSPHDQXACIRTA-UHFFFAOYSA-N 0.000 description 1
JPZKJABGOSPYDD-UHFFFAOYSA-N n-benzylmethanesulfonamide Chemical group CS(=O)(=O)NCC1=CC=CC=C1 JPZKJABGOSPYDD-UHFFFAOYSA-N 0.000 description 1
JKLMQPFJRZSOBQ-UHFFFAOYSA-N n-cyclohexylmethanesulfonamide Chemical compound CS(=O)(=O)NC1CCCCC1 JKLMQPFJRZSOBQ-UHFFFAOYSA-N 0.000 description 1
QKIWHADSHFVRFN-UHFFFAOYSA-N n-propan-2-ylbenzenesulfonamide Chemical group CC(C)NS(=O)(=O)C1=CC=CC=C1 QKIWHADSHFVRFN-UHFFFAOYSA-N 0.000 description 1
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
239000002674 ointment Substances 0.000 description 1
229910052625 palygorskite Inorganic materials 0.000 description 1
230000002688 persistence Effects 0.000 description 1
235000021317 phosphate Nutrition 0.000 description 1
150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
229920000056 polyoxyethylene ether Polymers 0.000 description 1
239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 description 1
235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 description 1
229920002451 polyvinyl alcohol Polymers 0.000 description 1
235000019422 polyvinyl alcohol Nutrition 0.000 description 1
229940068984 polyvinyl alcohol Drugs 0.000 description 1
230000002035 prolonged effect Effects 0.000 description 1
239000003380 propellant Substances 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
229910052903 pyrophyllite Inorganic materials 0.000 description 1
239000010453 quartz Substances 0.000 description 1
239000000376 reactant Substances 0.000 description 1
239000011435 rock Substances 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
238000010898 silica gel chromatography Methods 0.000 description 1
150000004760 silicates Chemical class 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
235000015424 sodium Nutrition 0.000 description 1
230000003595 spectral effect Effects 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
150000003900 succinic acid esters Chemical class 0.000 description 1
150000005846 sugar alcohols Polymers 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
239000011593 sulfur Substances 0.000 description 1
150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
239000000725 suspension Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
238000012360 testing method Methods 0.000 description 1
239000004753 textile Substances 0.000 description 1
238000004809 thin layer chromatography Methods 0.000 description 1
LMYRWZFENFIFIT-UHFFFAOYSA-N toluene-4-sulfonamide Chemical compound CC1=CC=C(S(N)(=O)=O)C=C1 LMYRWZFENFIFIT-UHFFFAOYSA-N 0.000 description 1
IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
238000009827 uniform distribution Methods 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1
239000002023 wood Substances 0.000 description 1

Classifications

- 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
- A01N41/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom
- A01N41/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom containing a sulfur-to-oxygen double bond
- A01N41/04—Sulfonic acids; Derivatives thereof
- A01N41/06—Sulfonic acid amides

Landscapes

Life Sciences & Earth Sciences (AREA)
Agronomy & Crop Science (AREA)
Pest Control & Pesticides (AREA)
Plant Pathology (AREA)
Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Dentistry (AREA)
General Health & Medical Sciences (AREA)
Wood Science & Technology (AREA)
Zoology (AREA)
Environmental Sciences (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)

CA302,748A 1977-06-09 1978-05-05 Sulfonamides n- [[arylformimidoyl]methylamino]thio]-n- substituees Expired CA1110656A (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US80489077A	1977-06-09	1977-06-09
US804,890		1977-06-09

Publications (1)

Publication Number	Publication Date
CA1110656A true CA1110656A (fr)	1981-10-13

Family

ID=25190131

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA302,748A Expired CA1110656A (fr)	1977-06-09	1978-05-05	Sulfonamides n- [[arylformimidoyl]methylamino]thio]-n- substituees

Country Status (12)

Country	Link
JP (1)	JPS545925A (fr)
AU (1)	AU515729B2 (fr)
BE (1)	BE867985A (fr)
CA (1)	CA1110656A (fr)
DE (1)	DE2823355A1 (fr)
DK (1)	DK227878A (fr)
FR (1)	FR2393792A1 (fr)
GB (1)	GB1597909A (fr)
IT (1)	IT7849782A0 (fr)
NL (1)	NL7805551A (fr)
NZ (1)	NZ187220A (fr)
ZA (1)	ZA782801B (fr)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
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
US4413013A (en)	1979-06-22	1983-11-01	The Upjohn Company	Sulfonamide compounds, compositions and methods for combatting insects
JPS63230609A (ja) *	1987-03-20	1988-09-27	Fumakiraa Kk	害虫駆除剤
US4877901A (en) *	1988-10-28	1989-10-31	The Goodyear Tire & Rubber Company	Process for synthesizing N,N'-dithiobis(sulfonamides)
EP1951664A1 (fr) *	2005-11-22	2008-08-06	Sumitomo Chemical Company, Limited	Composés organiques du soufre et utilisation de ceux-ci en tant qu'arthropodicides

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
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

1978
- 1978-05-05 CA CA302,748A patent/CA1110656A/fr not_active Expired
- 1978-05-10 NZ NZ187220A patent/NZ187220A/xx unknown
- 1978-05-16 ZA ZA00782801A patent/ZA782801B/xx unknown
- 1978-05-19 AU AU36273/78A patent/AU515729B2/en not_active Expired
- 1978-05-23 NL NL7805551A patent/NL7805551A/xx not_active Application Discontinuation
- 1978-05-23 GB GB21283/78A patent/GB1597909A/en not_active Expired
- 1978-05-23 DK DK227878A patent/DK227878A/da unknown
- 1978-05-29 DE DE19782823355 patent/DE2823355A1/de not_active Withdrawn
- 1978-06-08 FR FR787817156A patent/FR2393792A1/fr active Granted
- 1978-06-08 IT IT7849782A patent/IT7849782A0/it unknown
- 1978-06-09 BE BE188460A patent/BE867985A/fr not_active IP Right Cessation
- 1978-06-09 JP JP6975678A patent/JPS545925A/ja active Pending

Also Published As

Publication number	Publication date
AU515729B2 (en)	1981-04-30
BE867985A (fr)	1978-12-11
FR2393792A1 (fr)	1979-01-05
JPS545925A (en)	1979-01-17
DE2823355A1 (de)	1978-12-21
ZA782801B (en)	1979-05-30
FR2393792B1 (fr)	1983-12-23
NZ187220A (en)	1980-12-19
GB1597909A (en)	1981-09-16
IT7849782A0 (it)	1978-06-08
DK227878A (da)	1978-12-10
AU3627378A (en)	1979-11-22
NL7805551A (nl)	1978-12-12

Legal Events

Date	Code	Title	Description
1998-10-13	MKEX	Expiry

Publication	Publication Date	Title
US5075293A (en)	1991-12-24	((N-heterocyclyl)carbonyl)phosphoramidothioate ester insecticides
JPH0660176B2 (ja)	1994-08-10	ピラゾールスルホニルウレア誘導体、製法および選択性除草剤
CA1295618C (fr)	1992-02-11	N-acyl-n'-alkylcarbonylhydrazines substituees en n', a proprietes insecticides
GB1578711A (en)	1980-11-05	N - (phosphinyl-amino)thiomethylcarbamate compounds
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