CA1086643A - Thiophenes utiles dans la lutte contre certains arthropodes - Google Patents

Thiophenes utiles dans la lutte contre certains arthropodes

Info

Publication number: CA1086643A
Authority: CA; Canada
Prior art keywords: thiophene; diphenyl; phenyl; mites; mole
Prior art date: 1976-06-01
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

CA269,731A

Other languages

English (en)

Inventor

Douglas I. Relyea

Winchester L. Hubbard

Robert E. Grahame, Jr.

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.)

Uniroyal Inc

Original Assignee

Uniroyal Inc

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.)

1976-06-01

Filing date

1977-01-14

Publication date

1980-09-30

1977-01-14 Application filed by Uniroyal Inc filed Critical Uniroyal Inc

1980-09-30 Application granted granted Critical

1980-09-30 Publication of CA1086643A publication Critical patent/CA1086643A/fr

Status Expired legal-status Critical Current

Links

229930192474 thiophene Natural products 0.000 title claims abstract description 69
150000003577 thiophenes Chemical class 0.000 title claims abstract description 20
241000238421 Arthropoda Species 0.000 title description 4
241000238876 Acari Species 0.000 claims abstract description 30
241000607479 Yersinia pestis Species 0.000 claims abstract description 20
150000001875 compounds Chemical class 0.000 claims abstract description 14
241000238631 Hexapoda Species 0.000 claims abstract description 11
YTPLMLYBLZKORZ-UHFFFAOYSA-N Divinylene sulfide Natural products C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 114
238000000034 method Methods 0.000 claims description 22
241000497192 Phyllocoptruta oleivora Species 0.000 claims description 9
PJRGDKFLFAYRBV-UHFFFAOYSA-N 2-phenylthiophene Chemical compound C1=CSC(C=2C=CC=CC=2)=C1 PJRGDKFLFAYRBV-UHFFFAOYSA-N 0.000 claims description 7
FKHVUWRLXRMJLF-UHFFFAOYSA-N 2,4-diphenylthiophene Chemical compound C=1SC(C=2C=CC=CC=2)=CC=1C1=CC=CC=C1 FKHVUWRLXRMJLF-UHFFFAOYSA-N 0.000 claims description 6
QOYCSQBDTFMQSG-UHFFFAOYSA-N 2-(3-chlorophenyl)thiophene Chemical compound ClC1=CC=CC(C=2SC=CC=2)=C1 QOYCSQBDTFMQSG-UHFFFAOYSA-N 0.000 claims description 5
HWKZNRABKQDKTC-UHFFFAOYSA-N 2,5-diphenylthiophene Chemical compound C=1C=C(C=2C=CC=CC=2)SC=1C1=CC=CC=C1 HWKZNRABKQDKTC-UHFFFAOYSA-N 0.000 claims description 4
IIUDZDPILDMBFH-UHFFFAOYSA-N 2-(4-propan-2-ylphenyl)thiophene Chemical compound C1=CC(C(C)C)=CC=C1C1=CC=CS1 IIUDZDPILDMBFH-UHFFFAOYSA-N 0.000 claims description 4
YKTPNHVEYBMYLV-UHFFFAOYSA-N 2-bromo-3,5-diphenylthiophene Chemical compound BrC=1SC(C=2C=CC=CC=2)=CC=1C1=CC=CC=C1 YKTPNHVEYBMYLV-UHFFFAOYSA-N 0.000 claims description 4
230000000895 acaricidal effect Effects 0.000 claims description 4
230000000749 insecticidal effect Effects 0.000 claims description 4
TWKDIVDAGCWHES-UHFFFAOYSA-N 2-(4-methoxyphenyl)thiophene Chemical compound C1=CC(OC)=CC=C1C1=CC=CS1 TWKDIVDAGCWHES-UHFFFAOYSA-N 0.000 claims description 3
YRKAJCGUTWECCT-UHFFFAOYSA-N 2-(4-nitrophenyl)thiophene Chemical compound C1=CC([N+](=O)[O-])=CC=C1C1=CC=CS1 YRKAJCGUTWECCT-UHFFFAOYSA-N 0.000 claims 2
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract description 37
125000001424 substituent group Chemical group 0.000 abstract description 10
230000001276 controlling effect Effects 0.000 abstract 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 52
239000000126 substance Substances 0.000 description 33
239000000460 chlorine Substances 0.000 description 30
239000000203 mixture Chemical class 0.000 description 26
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 26
RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 23
125000004432 carbon atom Chemical group C* 0.000 description 23
229910000037 hydrogen sulfide Inorganic materials 0.000 description 23
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 21
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
229910052801 chlorine Inorganic materials 0.000 description 21
-1 methoxy, methylthio Chemical group 0.000 description 21
239000000243 solution Substances 0.000 description 21
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 16
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 16
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 16
229910052794 bromium Inorganic materials 0.000 description 16
239000011737 fluorine Substances 0.000 description 16
229910052731 fluorine Inorganic materials 0.000 description 16
CYQAYERJWZKYML-UHFFFAOYSA-N phosphorus pentasulfide Chemical compound S1P(S2)(=S)SP3(=S)SP1(=S)SP2(=S)S3 CYQAYERJWZKYML-UHFFFAOYSA-N 0.000 description 16
239000008096 xylene Substances 0.000 description 16
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 15
229910052739 hydrogen Inorganic materials 0.000 description 14
239000001257 hydrogen Substances 0.000 description 14
238000001953 recrystallisation Methods 0.000 description 14
241000196324 Embryophyta Species 0.000 description 13
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 13
229950005499 carbon tetrachloride Drugs 0.000 description 13
229910001220 stainless steel Inorganic materials 0.000 description 13
239000010935 stainless steel Substances 0.000 description 13
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 12
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 11
239000000047 product Substances 0.000 description 11
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 10
125000000217 alkyl group Chemical group 0.000 description 10
238000001914 filtration Methods 0.000 description 10
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 9
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
125000003545 alkoxy group Chemical group 0.000 description 9
239000012043 crude product Substances 0.000 description 9
JWUKZUIGOJBEPC-UHFFFAOYSA-N phenyl thiohypochlorite Chemical compound ClSC1=CC=CC=C1 JWUKZUIGOJBEPC-UHFFFAOYSA-N 0.000 description 9
239000011541 reaction mixture Substances 0.000 description 9
229910052799 carbon Inorganic materials 0.000 description 8
238000001704 evaporation Methods 0.000 description 8
230000008020 evaporation Effects 0.000 description 8
CHXZRHMQQRUVHF-UHFFFAOYSA-N 2-hex-5-en-1,3-diynyl-5-prop-1-ynylthiophene Chemical compound CC#CC1=CC=C(C#CC#CC=C)S1 CHXZRHMQQRUVHF-UHFFFAOYSA-N 0.000 description 7
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 7
125000005843 halogen group Chemical group 0.000 description 7
150000002431 hydrogen Chemical group 0.000 description 7
125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 7
239000002904 solvent Substances 0.000 description 7
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical group C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 6
241001465754 Metazoa Species 0.000 description 6
239000003153 chemical reaction reagent Substances 0.000 description 6
ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 6
229910052736 halogen Inorganic materials 0.000 description 6
150000002367 halogens Chemical class 0.000 description 6
125000004970 halomethyl group Chemical group 0.000 description 6
239000007787 solid Substances 0.000 description 6
238000001228 spectrum Methods 0.000 description 6
239000007921 spray Substances 0.000 description 6
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
238000003756 stirring Methods 0.000 description 5
125000000446 sulfanediyl group Chemical group *S* 0.000 description 5
SYAUXTHXMQIDNC-UHFFFAOYSA-N 2-(3,4-dimethylphenyl)thiophene Chemical compound C1=C(C)C(C)=CC=C1C1=CC=CS1 SYAUXTHXMQIDNC-UHFFFAOYSA-N 0.000 description 4
229920000742 Cotton Polymers 0.000 description 4
GUUVPOWQJOLRAS-UHFFFAOYSA-N Diphenyl disulfide Chemical compound C=1C=CC=CC=1SSC1=CC=CC=C1 GUUVPOWQJOLRAS-UHFFFAOYSA-N 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
239000000443 aerosol Substances 0.000 description 4
125000003118 aryl group Chemical group 0.000 description 4
239000004305 biphenyl Substances 0.000 description 4
RBHJBMIOOPYDBQ-UHFFFAOYSA-N carbon dioxide;propan-2-one Chemical compound O=C=O.CC(C)=O RBHJBMIOOPYDBQ-UHFFFAOYSA-N 0.000 description 4
238000004821 distillation Methods 0.000 description 4
239000000706 filtrate Substances 0.000 description 4
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 4
125000001624 naphthyl group Chemical group 0.000 description 4
BNJMRELGMDUDDB-UHFFFAOYSA-N $l^{1}-sulfanylbenzene Chemical compound [S]C1=CC=CC=C1 BNJMRELGMDUDDB-UHFFFAOYSA-N 0.000 description 3
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
JQJPBYFTQAANLE-UHFFFAOYSA-N Butyl nitrite Chemical compound CCCCON=O JQJPBYFTQAANLE-UHFFFAOYSA-N 0.000 description 3
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical group O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 3
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 3
UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
125000004414 alkyl thio group Chemical group 0.000 description 3
125000005530 alkylenedioxy group Chemical group 0.000 description 3
239000003795 chemical substances by application Substances 0.000 description 3
229960001701 chloroform Drugs 0.000 description 3
238000001816 cooling Methods 0.000 description 3
XTVVROIMIGLXTD-UHFFFAOYSA-N copper(II) nitrate Chemical compound [Cu+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O XTVVROIMIGLXTD-UHFFFAOYSA-N 0.000 description 3
125000000753 cycloalkyl group Chemical group 0.000 description 3
125000001153 fluoro group Chemical group F* 0.000 description 3
235000013305 food Nutrition 0.000 description 3
238000003359 percent control normalization Methods 0.000 description 3
239000011574 phosphorus Substances 0.000 description 3
229910052698 phosphorus Inorganic materials 0.000 description 3
235000014786 phosphorus Nutrition 0.000 description 3
239000012808 vapor phase Substances 0.000 description 3
NILHSXARFDXGTH-UHFFFAOYSA-N 2,3-diphenyl-5-(3,4,5-trimethoxyphenyl)thiophene Chemical compound COC1=C(OC)C(OC)=CC(C=2SC(=C(C=2)C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 NILHSXARFDXGTH-UHFFFAOYSA-N 0.000 description 2
GGJDJCBJLDHXEZ-UHFFFAOYSA-N 2-phenyl-5-phenylsulfanylthiophene Chemical compound C=1C=CC=CC=1SC(S1)=CC=C1C1=CC=CC=C1 GGJDJCBJLDHXEZ-UHFFFAOYSA-N 0.000 description 2
DOLQYFPDPKPQSS-UHFFFAOYSA-N 3,4-dimethylaniline Chemical compound CC1=CC=C(N)C=C1C DOLQYFPDPKPQSS-UHFFFAOYSA-N 0.000 description 2
241000256118 Aedes aegypti Species 0.000 description 2
241000255925 Diptera Species 0.000 description 2
241000219146 Gossypium Species 0.000 description 2
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
244000141359 Malus pumila Species 0.000 description 2
240000004658 Medicago sativa Species 0.000 description 2
235000017587 Medicago sativa ssp. sativa Nutrition 0.000 description 2
229910000831 Steel Inorganic materials 0.000 description 2
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
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125000004429 atom Chemical group 0.000 description 2
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QGGZBXOADPVUPN-UHFFFAOYSA-N dihydrochalcone Chemical compound C=1C=CC=CC=1C(=O)CCC1=CC=CC=C1 QGGZBXOADPVUPN-UHFFFAOYSA-N 0.000 description 2
238000010790 dilution Methods 0.000 description 2
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XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 2
229910052500 inorganic mineral Inorganic materials 0.000 description 2
239000007788 liquid Substances 0.000 description 2
125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 2
235000010755 mineral Nutrition 0.000 description 2
239000011707 mineral Substances 0.000 description 2
238000005580 one pot reaction Methods 0.000 description 2
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125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 2
238000002360 preparation method Methods 0.000 description 2
150000003254 radicals Chemical class 0.000 description 2
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150000004760 silicates Chemical class 0.000 description 2
239000011734 sodium Substances 0.000 description 2
241000894007 species Species 0.000 description 2
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239000011593 sulfur Substances 0.000 description 2
229910052717 sulfur Inorganic materials 0.000 description 2
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125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 2
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UAOUIVVJBYDFKD-XKCDOFEDSA-N (1R,9R,10S,11R,12R,15S,18S,21R)-10,11,21-trihydroxy-8,8-dimethyl-14-methylidene-4-(prop-2-enylamino)-20-oxa-5-thia-3-azahexacyclo[9.7.2.112,15.01,9.02,6.012,18]henicosa-2(6),3-dien-13-one Chemical compound C([C@@H]1[C@@H](O)[C@@]23C(C1=C)=O)C[C@H]2[C@]12C(N=C(NCC=C)S4)=C4CC(C)(C)[C@H]1[C@H](O)[C@]3(O)OC2 UAOUIVVJBYDFKD-XKCDOFEDSA-N 0.000 description 1
IUSARDYWEPUTPN-OZBXUNDUSA-N (2r)-n-[(2s,3r)-4-[[(4s)-6-(2,2-dimethylpropyl)spiro[3,4-dihydropyrano[2,3-b]pyridine-2,1'-cyclobutane]-4-yl]amino]-3-hydroxy-1-[3-(1,3-thiazol-2-yl)phenyl]butan-2-yl]-2-methoxypropanamide Chemical compound C([C@H](NC(=O)[C@@H](C)OC)[C@H](O)CN[C@@H]1C2=CC(CC(C)(C)C)=CN=C2OC2(CCC2)C1)C(C=1)=CC=CC=1C1=NC=CS1 IUSARDYWEPUTPN-OZBXUNDUSA-N 0.000 description 1
GBIYAVWBYTZRNJ-UHFFFAOYSA-N (3-nitrophenyl) thiohypochlorite Chemical compound [O-][N+](=O)C1=CC=CC(SCl)=C1 GBIYAVWBYTZRNJ-UHFFFAOYSA-N 0.000 description 1
UDQTXCHQKHIQMH-KYGLGHNPSA-N (3ar,5s,6s,7r,7ar)-5-(difluoromethyl)-2-(ethylamino)-5,6,7,7a-tetrahydro-3ah-pyrano[3,2-d][1,3]thiazole-6,7-diol Chemical compound S1C(NCC)=N[C@H]2[C@@H]1O[C@H](C(F)F)[C@@H](O)[C@@H]2O UDQTXCHQKHIQMH-KYGLGHNPSA-N 0.000 description 1
HUWSZNZAROKDRZ-RRLWZMAJSA-N (3r,4r)-3-azaniumyl-5-[[(2s,3r)-1-[(2s)-2,3-dicarboxypyrrolidin-1-yl]-3-methyl-1-oxopentan-2-yl]amino]-5-oxo-4-sulfanylpentane-1-sulfonate Chemical compound OS(=O)(=O)CC[C@@H](N)[C@@H](S)C(=O)N[C@@H]([C@H](C)CC)C(=O)N1CCC(C(O)=O)[C@H]1C(O)=O HUWSZNZAROKDRZ-RRLWZMAJSA-N 0.000 description 1
OMBVEVHRIQULKW-DNQXCXABSA-M (3r,5r)-7-[3-(4-fluorophenyl)-8-oxo-7-phenyl-1-propan-2-yl-5,6-dihydro-4h-pyrrolo[2,3-c]azepin-2-yl]-3,5-dihydroxyheptanoate Chemical compound O=C1C=2N(C(C)C)C(CC[C@@H](O)C[C@@H](O)CC([O-])=O)=C(C=3C=CC(F)=CC=3)C=2CCCN1C1=CC=CC=C1 OMBVEVHRIQULKW-DNQXCXABSA-M 0.000 description 1
FGDJVKNEHXILOJ-UHFFFAOYSA-N 1,2-diphenyl-4-(3,4,5-trimethoxyphenyl)butane-1,4-dione Chemical compound COC1=C(OC)C(OC)=CC(C(=O)CC(C(=O)C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 FGDJVKNEHXILOJ-UHFFFAOYSA-N 0.000 description 1
SGUVLZREKBPKCE-UHFFFAOYSA-N 1,5-diazabicyclo[4.3.0]-non-5-ene Chemical compound C1CCN=C2CCCN21 SGUVLZREKBPKCE-UHFFFAOYSA-N 0.000 description 1
XBDXMDVEZLOGMC-UHFFFAOYSA-N 1-(chloromethyl)-3-fluorobenzene Chemical compound FC1=CC=CC(CCl)=C1 XBDXMDVEZLOGMC-UHFFFAOYSA-N 0.000 description 1
KQZLRWGGWXJPOS-NLFPWZOASA-N 1-[(1R)-1-(2,4-dichlorophenyl)ethyl]-6-[(4S,5R)-4-[(2S)-2-(hydroxymethyl)pyrrolidin-1-yl]-5-methylcyclohexen-1-yl]pyrazolo[3,4-b]pyrazine-3-carbonitrile Chemical compound ClC1=C(C=CC(=C1)Cl)[C@@H](C)N1N=C(C=2C1=NC(=CN=2)C1=CC[C@@H]([C@@H](C1)C)N1[C@@H](CCC1)CO)C#N KQZLRWGGWXJPOS-NLFPWZOASA-N 0.000 description 1
PKYYEBIXSORDNK-UHFFFAOYSA-N 1-methyl-4-methylsulfanylnaphthalene Chemical compound C1=CC=C2C(SC)=CC=C(C)C2=C1 PKYYEBIXSORDNK-UHFFFAOYSA-N 0.000 description 1
DJMUYABFXCIYSC-UHFFFAOYSA-N 1H-phosphole Chemical compound C=1C=CPC=1 DJMUYABFXCIYSC-UHFFFAOYSA-N 0.000 description 1
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CDULGHZNHURECF-UHFFFAOYSA-N 2,3-dimethylaniline 2,4-dimethylaniline 2,5-dimethylaniline 2,6-dimethylaniline 3,4-dimethylaniline 3,5-dimethylaniline Chemical group CC1=CC=C(N)C(C)=C1.CC1=CC=C(C)C(N)=C1.CC1=CC(C)=CC(N)=C1.CC1=CC=C(N)C=C1C.CC1=CC=CC(N)=C1C.CC1=CC=CC(C)=C1N CDULGHZNHURECF-UHFFFAOYSA-N 0.000 description 1
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom 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 ring carbon atoms
- C07D333/28—Halogen atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/08—Hydrogen atoms or radicals containing only hydrogen and carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/12—Radicals substituted by halogen atoms or nitro or nitroso radicals
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/14—Radicals substituted by singly bound hetero atoms other than halogen
- C07D333/16—Radicals substituted by singly bound hetero atoms other than halogen by oxygen atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/14—Radicals substituted by singly bound hetero atoms other than halogen
- C07D333/18—Radicals substituted by singly bound hetero atoms other than halogen by sulfur atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom 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 ring carbon atoms
- C07D333/30—Hetero atoms other than halogen
- C07D333/34—Sulfur atoms

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Plural Heterocyclic Compounds (AREA)

CA269,731A 1976-06-01 1977-01-14 Thiophenes utiles dans la lutte contre certains arthropodes Expired CA1086643A (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US69166076A	1976-06-01	1976-06-01
US691,660		1976-06-01

Publications (1)

Publication Number	Publication Date
CA1086643A true CA1086643A (fr)	1980-09-30

Family

ID=24777438

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA269,731A Expired CA1086643A (fr)	1976-06-01	1977-01-14	Thiophenes utiles dans la lutte contre certains arthropodes

Country Status (5)

Country	Link
JP (1)	JPS52148067A (fr)
CA (1)	CA1086643A (fr)
DE (1)	DE2724494A1 (fr)
FR (1)	FR2353228A1 (fr)
NL (1)	NL7706027A (fr)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4426524A (en)	1980-09-02	1984-01-17	Fmc Corporation	Heterocyclic substituted benzyl alcohol, insecticidal ester derivatives, and intermediates
NZ211146A (en) *	1984-02-29	1987-10-30	Merck & Co Inc	2,5-diaryl-tetrahydrothiophene derivatives and pharmaceutical compositions
US4999436A (en) *	1987-09-22	1991-03-12	Merck & Co., Inc.	Aryl-substituted thiophene 3-ols, derivatives and analogs useful as lipoxgenase inhibitors
DE10353281A1 (de)	2003-11-14	2005-06-16	Bayer Cropscience Ag	Wirkstoffkombination mit insektiziden und akariziden Eigenschaften
DE102007045922A1 (de)	2007-09-26	2009-04-02	Bayer Cropscience Ag	Wirkstoffkombinationen mit insektiziden und akariziden Eigenschaften
EP2127522A1 (fr)	2008-05-29	2009-12-02	Bayer CropScience AG	Combinaisons de principes actifs presentant des propriétés insecticides et acaricides
EP2382865A1 (fr)	2010-04-28	2011-11-02	Bayer CropScience AG	Combinaisons d'agents actifs synergiques

1977
- 1977-01-14 CA CA269,731A patent/CA1086643A/fr not_active Expired
- 1977-05-27 FR FR7716377A patent/FR2353228A1/fr not_active Withdrawn
- 1977-05-31 DE DE19772724494 patent/DE2724494A1/de active Pending
- 1977-05-31 JP JP6291877A patent/JPS52148067A/ja active Granted
- 1977-06-01 NL NL7706027A patent/NL7706027A/xx not_active Application Discontinuation

Also Published As

Publication number	Publication date
NL7706027A (nl)	1977-12-05
JPS52148067A (en)	1977-12-08
JPS558506B2 (fr)	1980-03-04
DE2724494A1 (de)	1977-12-08
FR2353228A1 (fr)	1977-12-30

Legal Events

Date	Code	Title	Description
1997-09-30	MKEX	Expiry

Publication	Publication Date	Title
CA1082205A (fr)	1980-07-22	Esters d'acides 2-alkyle superieur-3-hydroxy-1,4- naphtaquinone-carboxyliques efficaces comme acaracides et aphicides
US4174405A (en)	1979-11-13	Thiophenes useful in control of acarids
US4303669A (en)	1981-12-01	Hybrid 1,3-dione-carbamate compounds
NZ280972A (en)	1997-11-24	N-arylamidrazones and pesticidal compositions containing them or n-arylhydrazides or n-arylhydrazinoyl halides
CA1086643A (fr)	1980-09-30	Thiophenes utiles dans la lutte contre certains arthropodes
CA1161059A (fr)	1984-01-24	Derives de thiouree et d'isothiouree a qualites pesticides
CA1087620A (fr)	1980-10-14	Compose asymetrique de bis-carbamate
US2939871A (en)	1960-06-07	2-chloro-substituted tetrahydrothiophene oxides, and composition containing the same
US3928382A (en)	1975-12-23	2-Imino-1,3-dithietane
US4607035A (en)	1986-08-19	1-phenoxy(phenylthio)-4-arylalkynyloxy-benzene derivatives endowed with a juvenile hormonic and an acaricide activity
DE2416054A1 (de)	1974-10-24	Verfahren und praeparate zur schaedlingsbekaempfung
US4197306A (en)	1980-04-08	Aryl-substituted thiazoles
DE2744385C2 (de)	1986-12-18	Biocide Mittel und Verfahren zur Herstellung der darin enthaltenen Wirkstoffe
US3812262A (en)	1974-05-21	Substituted propiolophenones used as plant fungicides
CA1072967A (fr)	1980-03-04	Thiophenes utiles pour la lutte contre certains arthropodes
US4197311A (en)	1980-04-08	Cyanomethyl trithiocarbonate compounds useful as ovicidal agents
US3032406A (en)	1962-05-01	Herbicidal method employing phenoxyalkylamines
PL95242B1 (fr)	1977-09-30
US3705177A (en)	1972-12-05	Substituted propiolophenone compounds
US2875123A (en)	1959-02-24	Hexachlorobicycloheptene sulfonic acids and derivatives as insecticides
US4009279A (en)	1977-02-22	Methods for controlling insects and acarina
US4028413A (en)	1977-06-07	Ketoxime carbamates
US3349115A (en)	1967-10-24	Sulfur-containing carbamate insecticides
US4022903A (en)	1977-05-10	α-Thienyl and α-substituted thienyl, phenyl and substituted phenyl cyclopropylomethanols useful as biodegradable insecticides and mollusicides
US4062951A (en)	1977-12-13	Organophosphorus compounds, compositions containing them and their method of use