GB1571422A - Benzamides and their use as insecticides - Google Patents
Benzamides and their use as insecticides Download PDFInfo
- Publication number
- GB1571422A GB1571422A GB4389/77A GB438977A GB1571422A GB 1571422 A GB1571422 A GB 1571422A GB 4389/77 A GB4389/77 A GB 4389/77A GB 438977 A GB438977 A GB 438977A GB 1571422 A GB1571422 A GB 1571422A
- Authority
- GB
- United Kingdom
- Prior art keywords
- compound
- thiadiazol
- amino
- chloro
- formula
- 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
- 239000002917 insecticide Substances 0.000 title abstract description 8
- 229940054066 benzamide antipsychotics Drugs 0.000 title description 4
- 150000003936 benzamides Chemical class 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 190
- 229910052739 hydrogen Inorganic materials 0.000 claims description 97
- 239000001257 hydrogen Substances 0.000 claims description 77
- 150000002431 hydrogen Chemical class 0.000 claims description 71
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 55
- -1 chloro, methoxy, bromo, iodo Chemical group 0.000 claims description 55
- 125000001246 bromo group Chemical group Br* 0.000 claims description 54
- 238000000034 method Methods 0.000 claims description 46
- 125000001153 fluoro group Chemical group F* 0.000 claims description 39
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 36
- 241000238631 Hexapoda Species 0.000 claims description 31
- 239000000203 mixture Substances 0.000 claims description 30
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 30
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 29
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 28
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 25
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 18
- 239000012024 dehydrating agents Substances 0.000 claims description 17
- 125000004076 pyridyl group Chemical group 0.000 claims description 16
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 14
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims description 14
- 125000005843 halogen group Chemical group 0.000 claims description 14
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 14
- 125000005493 quinolyl group Chemical group 0.000 claims description 14
- 125000000335 thiazolyl group Chemical group 0.000 claims description 14
- 230000000749 insecticidal effect Effects 0.000 claims description 13
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 13
- 125000001544 thienyl group Chemical group 0.000 claims description 12
- NDXRPDJVAUCBOH-UHFFFAOYSA-N 2,6-dimethoxybenzoyl chloride Chemical compound COC1=CC=CC(OC)=C1C(Cl)=O NDXRPDJVAUCBOH-UHFFFAOYSA-N 0.000 claims description 10
- 125000004618 benzofuryl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 10
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 10
- 125000002541 furyl group Chemical group 0.000 claims description 10
- 229910052736 halogen Inorganic materials 0.000 claims description 10
- CHAYRXZJAZXJRB-UHFFFAOYSA-N n-[5-(4-chlorophenyl)-1,3,4-thiadiazol-2-yl]-2,6-dimethoxybenzamide Chemical compound COC1=CC=CC(OC)=C1C(=O)NC1=NN=C(C=2C=CC(Cl)=CC=2)S1 CHAYRXZJAZXJRB-UHFFFAOYSA-N 0.000 claims description 9
- 125000001624 naphthyl group Chemical group 0.000 claims description 8
- 239000007800 oxidant agent Substances 0.000 claims description 8
- OAVULPOOAHQYDZ-UHFFFAOYSA-N 5-(4-chlorophenyl)-1,3,4-thiadiazol-2-amine Chemical compound S1C(N)=NN=C1C1=CC=C(Cl)C=C1 OAVULPOOAHQYDZ-UHFFFAOYSA-N 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 6
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- 239000001301 oxygen Substances 0.000 claims description 6
- 239000000126 substance Substances 0.000 claims description 6
- IITOCTXMJQVOIO-UHFFFAOYSA-N 2,6-dimethoxy-n-[5-[3-(trifluoromethyl)phenyl]-1,3,4-thiadiazol-2-yl]benzamide Chemical compound COC1=CC=CC(OC)=C1C(=O)NC1=NN=C(C=2C=C(C=CC=2)C(F)(F)F)S1 IITOCTXMJQVOIO-UHFFFAOYSA-N 0.000 claims description 5
- RFHCVACSKBMWSO-UHFFFAOYSA-N 2,6-dimethoxy-n-[5-[4-(trifluoromethyl)phenyl]-1,3,4-thiadiazol-2-yl]benzamide Chemical compound COC1=CC=CC(OC)=C1C(=O)NC1=NN=C(C=2C=CC(=CC=2)C(F)(F)F)S1 RFHCVACSKBMWSO-UHFFFAOYSA-N 0.000 claims description 5
- UUHMUTDTJXUTMA-UHFFFAOYSA-N 2,6-dimethyl-n-[5-[4-(trifluoromethyl)phenyl]-1,3,4-thiadiazol-2-yl]benzamide Chemical compound CC1=CC=CC(C)=C1C(=O)NC1=NN=C(C=2C=CC(=CC=2)C(F)(F)F)S1 UUHMUTDTJXUTMA-UHFFFAOYSA-N 0.000 claims description 5
- FSQVKRMTZMKIHR-UHFFFAOYSA-N n-[5-(3-chlorophenyl)-1,3,4-thiadiazol-2-yl]-2,6-dimethoxybenzamide Chemical compound COC1=CC=CC(OC)=C1C(=O)NC1=NN=C(C=2C=C(Cl)C=CC=2)S1 FSQVKRMTZMKIHR-UHFFFAOYSA-N 0.000 claims description 5
- NIELLPWNUAZBGO-UHFFFAOYSA-N n-[5-(4-fluorophenyl)-1,3,4-thiadiazol-2-yl]-2,6-dimethoxybenzamide Chemical compound COC1=CC=CC(OC)=C1C(=O)NC1=NN=C(C=2C=CC(F)=CC=2)S1 NIELLPWNUAZBGO-UHFFFAOYSA-N 0.000 claims description 5
- SYANQAYNWFYMNV-UHFFFAOYSA-N n-[5-(4-fluorophenyl)-1,3,4-thiadiazol-2-yl]-2,6-dimethylbenzamide Chemical compound CC1=CC=CC(C)=C1C(=O)NC1=NN=C(C=2C=CC(F)=CC=2)S1 SYANQAYNWFYMNV-UHFFFAOYSA-N 0.000 claims description 5
- 150000004869 1,3,4-thiadiazoles Chemical class 0.000 claims description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- SLVMSTQNCGGXCU-UHFFFAOYSA-N n-[5-(4-chlorophenyl)-1,3,4-thiadiazol-2-yl]-2,6-dimethylbenzamide Chemical compound CC1=CC=CC(C)=C1C(=O)NC1=NN=C(C=2C=CC(Cl)=CC=2)S1 SLVMSTQNCGGXCU-UHFFFAOYSA-N 0.000 claims description 4
- NZHPBFGAAOMTIS-UHFFFAOYSA-N n-[5-[3,5-bis(trifluoromethyl)phenyl]-1,3,4-thiadiazol-2-yl]-2,6-dimethoxybenzamide Chemical compound COC1=CC=CC(OC)=C1C(=O)NC1=NN=C(C=2C=C(C=C(C=2)C(F)(F)F)C(F)(F)F)S1 NZHPBFGAAOMTIS-UHFFFAOYSA-N 0.000 claims description 4
- 229910052717 sulfur Chemical group 0.000 claims description 4
- 239000011593 sulfur Chemical group 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 3
- BXTGHJIBIBKFQA-UHFFFAOYSA-N n-[[(4-chlorobenzoyl)amino]carbamothioyl]-2,6-dimethoxybenzamide Chemical compound COC1=CC=CC(OC)=C1C(=O)NC(=S)NNC(=O)C1=CC=C(Cl)C=C1 BXTGHJIBIBKFQA-UHFFFAOYSA-N 0.000 claims description 3
- KXDAEFPNCMNJSK-UHFFFAOYSA-N benzene carboxamide Natural products NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims 4
- CFLAYISSADVCJH-UHFFFAOYSA-N 2,6-dimethylbenzoyl chloride Chemical compound CC1=CC=CC(C)=C1C(Cl)=O CFLAYISSADVCJH-UHFFFAOYSA-N 0.000 claims 3
- WRSVCKNLHZWSNJ-UHFFFAOYSA-N 5-(4-fluorophenyl)-1,3,4-thiadiazol-2-amine Chemical compound S1C(N)=NN=C1C1=CC=C(F)C=C1 WRSVCKNLHZWSNJ-UHFFFAOYSA-N 0.000 claims 2
- IKOYAQXGLSFYSH-UHFFFAOYSA-N 5-[4-(trifluoromethyl)phenyl]-1,3,4-thiadiazol-2-amine Chemical compound S1C(N)=NN=C1C1=CC=C(C(F)(F)F)C=C1 IKOYAQXGLSFYSH-UHFFFAOYSA-N 0.000 claims 2
- RZFOIFSHOGDXFZ-UHFFFAOYSA-N 2,6-dimethoxy-N-[[[3-(trifluoromethyl)benzoyl]amino]carbamothioyl]benzamide Chemical compound FC(C=1C=C(C(=O)NNC(=S)NC(C2=C(C=CC=C2OC)OC)=O)C=CC1)(F)F RZFOIFSHOGDXFZ-UHFFFAOYSA-N 0.000 claims 1
- RUMMUXGGBLRHCE-UHFFFAOYSA-N 2,6-dimethyl-N-[[[4-(trifluoromethyl)benzoyl]amino]carbamothioyl]benzamide Chemical compound FC(C1=CC=C(C(=O)NNC(=S)NC(C2=C(C=CC=C2C)C)=O)C=C1)(F)F RUMMUXGGBLRHCE-UHFFFAOYSA-N 0.000 claims 1
- JVPYRGXPTAPRJU-UHFFFAOYSA-N 5-(3-chlorophenyl)-1,3,4-thiadiazol-2-amine Chemical compound S1C(N)=NN=C1C1=CC=CC(Cl)=C1 JVPYRGXPTAPRJU-UHFFFAOYSA-N 0.000 claims 1
- OWEVQLAGEVSZQL-UHFFFAOYSA-N 5-[3-(trifluoromethyl)phenyl]-1,3,4-thiadiazol-2-amine Chemical compound S1C(N)=NN=C1C1=CC=CC(C(F)(F)F)=C1 OWEVQLAGEVSZQL-UHFFFAOYSA-N 0.000 claims 1
- FUYSZBXSPCNWKU-UHFFFAOYSA-N N-[[(3-chlorobenzoyl)amino]carbamothioyl]-2,6-dimethoxybenzamide Chemical compound ClC=1C=C(C(=O)NNC(=S)NC(C2=C(C=CC=C2OC)OC)=O)C=CC1 FUYSZBXSPCNWKU-UHFFFAOYSA-N 0.000 claims 1
- RTPARCYABBEYNC-UHFFFAOYSA-N N-[[(4-chlorobenzoyl)amino]carbamothioyl]-2,6-dimethylbenzamide Chemical compound ClC1=CC=C(C(=O)NNC(=S)NC(C2=C(C=CC=C2C)C)=O)C=C1 RTPARCYABBEYNC-UHFFFAOYSA-N 0.000 claims 1
- IOFNKOYCYDLFIZ-UHFFFAOYSA-N N-[[(4-fluorobenzoyl)amino]carbamothioyl]-2,6-dimethoxybenzamide Chemical compound FC1=CC=C(C(=O)NNC(=S)NC(C2=C(C=CC=C2OC)OC)=O)C=C1 IOFNKOYCYDLFIZ-UHFFFAOYSA-N 0.000 claims 1
- IRBIIKASWMYBSZ-UHFFFAOYSA-N N-[[(4-fluorobenzoyl)amino]carbamothioyl]-2,6-dimethylbenzamide Chemical compound FC1=CC=C(C(=O)NNC(=S)NC(C2=C(C=CC=C2C)C)=O)C=C1 IRBIIKASWMYBSZ-UHFFFAOYSA-N 0.000 claims 1
- IFOHYMJOLDOHJU-UHFFFAOYSA-N N-[[[3,5-bis(trifluoromethyl)benzoyl]amino]carbamothioyl]-2,6-dimethoxybenzamide Chemical compound FC(C=1C=C(C(=O)NNC(=S)NC(C2=C(C=CC=C2OC)OC)=O)C=C(C1)C(F)(F)F)(F)F IFOHYMJOLDOHJU-UHFFFAOYSA-N 0.000 claims 1
- 238000012360 testing method Methods 0.000 description 38
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 20
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 17
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 16
- 241000462639 Epilachna varivestis Species 0.000 description 16
- 238000002360 preparation method Methods 0.000 description 15
- 239000002904 solvent Substances 0.000 description 13
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 239000006185 dispersion Substances 0.000 description 11
- 239000000047 product Substances 0.000 description 11
- 239000007787 solid Substances 0.000 description 11
- 229940098779 methanesulfonic acid Drugs 0.000 description 10
- 241001521235 Spodoptera eridania Species 0.000 description 9
- 241000196324 Embryophyta Species 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 7
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000000843 powder Substances 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
- 240000003259 Brassica oleracea var. botrytis Species 0.000 description 5
- 241000255777 Lepidoptera Species 0.000 description 5
- 241000907661 Pieris rapae Species 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 235000013601 eggs Nutrition 0.000 description 5
- 239000003960 organic solvent Substances 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- 238000007363 ring formation reaction Methods 0.000 description 5
- 241000894007 species Species 0.000 description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 5
- 235000011299 Brassica oleracea var botrytis Nutrition 0.000 description 4
- 235000017647 Brassica oleracea var italica Nutrition 0.000 description 4
- 241000254173 Coleoptera Species 0.000 description 4
- 241000257186 Phormia regina Species 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000000543 intermediate Substances 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- 239000004094 surface-active agent Substances 0.000 description 4
- QUKGLNCXGVWCJX-UHFFFAOYSA-N 1,3,4-thiadiazol-2-amine Chemical class NC1=NN=CS1 QUKGLNCXGVWCJX-UHFFFAOYSA-N 0.000 description 3
- JCLPOIIWYKRWMD-UHFFFAOYSA-N 2,6-dimethoxy-n-(5-pyridin-4-yl-1,3,4-thiadiazol-2-yl)benzamide Chemical compound COC1=CC=CC(OC)=C1C(=O)NC1=NN=C(C=2C=CN=CC=2)S1 JCLPOIIWYKRWMD-UHFFFAOYSA-N 0.000 description 3
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 241000255896 Galleria mellonella Species 0.000 description 3
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 3
- ZEKVZXSIKMTOIV-UHFFFAOYSA-N N-[5-(4-hydroxyphenyl)-1,3,4-thiadiazol-2-yl]-2,6-dimethoxybenzamide Chemical compound COC1=CC=CC(OC)=C1C(=O)NC1=NN=C(C=2C=CC(O)=CC=2)S1 ZEKVZXSIKMTOIV-UHFFFAOYSA-N 0.000 description 3
- 244000046052 Phaseolus vulgaris Species 0.000 description 3
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 3
- 241000255993 Trichoplusia ni Species 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 230000010933 acylation Effects 0.000 description 3
- 238000005917 acylation reaction Methods 0.000 description 3
- 239000000908 ammonium hydroxide Substances 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 239000004495 emulsifiable concentrate Substances 0.000 description 3
- 229940032296 ferric chloride Drugs 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 230000002363 herbicidal effect Effects 0.000 description 3
- 238000005984 hydrogenation reaction Methods 0.000 description 3
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 3
- IFIMOLTUUWNOAE-UHFFFAOYSA-N n-[5-(3-hydroxyphenyl)-1,3,4-thiadiazol-2-yl]-2,6-dimethoxybenzamide Chemical compound COC1=CC=CC(OC)=C1C(=O)NC1=NN=C(C=2C=C(O)C=CC=2)S1 IFIMOLTUUWNOAE-UHFFFAOYSA-N 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 238000007243 oxidative cyclization reaction Methods 0.000 description 3
- 238000003359 percent control normalization Methods 0.000 description 3
- 239000003208 petroleum Substances 0.000 description 3
- 239000004033 plastic Substances 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 239000012312 sodium hydride Substances 0.000 description 3
- 229910000104 sodium hydride Inorganic materials 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- JCWLSAUVVFLKPG-UHFFFAOYSA-N thiadiazole;hydrochloride Chemical compound Cl.C1=CSN=N1 JCWLSAUVVFLKPG-UHFFFAOYSA-N 0.000 description 3
- SRVJKTDHMYAMHA-WUXMJOGZSA-N thioacetazone Chemical compound CC(=O)NC1=CC=C(\C=N\NC(N)=S)C=C1 SRVJKTDHMYAMHA-WUXMJOGZSA-N 0.000 description 3
- CPRPLWKGHKHUOQ-UHFFFAOYSA-N 2,6-dichloro-n-[5-(4-chlorophenyl)-1,3,4-thiadiazol-2-yl]benzamide Chemical compound C1=CC(Cl)=CC=C1C(S1)=NN=C1NC(=O)C1=C(Cl)C=CC=C1Cl CPRPLWKGHKHUOQ-UHFFFAOYSA-N 0.000 description 2
- ZVWRMLFYEFYNPZ-UHFFFAOYSA-N 2,6-dimethoxy-n-(5-quinolin-2-yl-1,3,4-thiadiazol-2-yl)benzamide Chemical compound COC1=CC=CC(OC)=C1C(=O)NC1=NN=C(C=2N=C3C=CC=CC3=CC=2)S1 ZVWRMLFYEFYNPZ-UHFFFAOYSA-N 0.000 description 2
- KTWDTPBHCWJWGJ-UHFFFAOYSA-N 5-pyridin-4-yl-1,3,4-thiadiazol-2-amine Chemical compound S1C(N)=NN=C1C1=CC=NC=C1 KTWDTPBHCWJWGJ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- UGFXGRGNIXLGFM-UHFFFAOYSA-N [(4-chlorobenzoyl)amino]thiourea Chemical compound NC(=S)NNC(=O)C1=CC=C(Cl)C=C1 UGFXGRGNIXLGFM-UHFFFAOYSA-N 0.000 description 2
- 239000000443 aerosol Substances 0.000 description 2
- SOIFLUNRINLCBN-UHFFFAOYSA-N ammonium thiocyanate Chemical compound [NH4+].[S-]C#N SOIFLUNRINLCBN-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 235000013339 cereals Nutrition 0.000 description 2
- 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 2
- 235000005911 diet Nutrition 0.000 description 2
- 230000037213 diet Effects 0.000 description 2
- 239000003995 emulsifying agent Substances 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 229940044631 ferric chloride hexahydrate Drugs 0.000 description 2
- BRWIZMBXBAOCCF-UHFFFAOYSA-N hydrazinecarbothioamide Chemical compound NNC(N)=S BRWIZMBXBAOCCF-UHFFFAOYSA-N 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- NQXWGWZJXJUMQB-UHFFFAOYSA-K iron trichloride hexahydrate Chemical compound O.O.O.O.O.O.[Cl-].Cl[Fe+]Cl NQXWGWZJXJUMQB-UHFFFAOYSA-K 0.000 description 2
- 230000000974 larvacidal effect Effects 0.000 description 2
- 210000004185 liver Anatomy 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 229910052901 montmorillonite Inorganic materials 0.000 description 2
- QROCASVLPNBFTL-UHFFFAOYSA-N n-[5-(1,3-benzothiazol-2-yl)-1,3,4-thiadiazol-2-yl]-2,6-dimethoxybenzamide Chemical compound COC1=CC=CC(OC)=C1C(=O)NC1=NN=C(C=2SC3=CC=CC=C3N=2)S1 QROCASVLPNBFTL-UHFFFAOYSA-N 0.000 description 2
- GWYGGKFPLICUTR-UHFFFAOYSA-N n-[5-(2-chlorophenyl)-1,3,4-thiadiazol-2-yl]-2,6-dimethoxybenzamide Chemical compound COC1=CC=CC(OC)=C1C(=O)NC1=NN=C(C=2C(=CC=CC=2)Cl)S1 GWYGGKFPLICUTR-UHFFFAOYSA-N 0.000 description 2
- OOXLBQJCCGJSKN-UHFFFAOYSA-N n-[5-(4-acetamidophenyl)-1,3,4-thiadiazol-2-yl]-2,6-dimethoxybenzamide Chemical compound COC1=CC=CC(OC)=C1C(=O)NC1=NN=C(C=2C=CC(NC(C)=O)=CC=2)S1 OOXLBQJCCGJSKN-UHFFFAOYSA-N 0.000 description 2
- XRGCUWJCKHOLGC-UHFFFAOYSA-N n-[[(4-hydroxybenzoyl)amino]carbamothioyl]-2,6-dimethoxybenzamide Chemical compound COC1=CC=CC(OC)=C1C(=O)NC(=S)NNC(=O)C1=CC=C(O)C=C1 XRGCUWJCKHOLGC-UHFFFAOYSA-N 0.000 description 2
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical class C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000003380 propellant Substances 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 238000001308 synthesis method Methods 0.000 description 2
- CUWHXIJMTMMRTI-UHFFFAOYSA-N thiadiazol-4-amine Chemical class NC1=CSN=N1 CUWHXIJMTMMRTI-UHFFFAOYSA-N 0.000 description 2
- 239000002023 wood Substances 0.000 description 2
- 125000004521 1,3,4-thiadiazol-2-yl group Chemical group S1C(=NN=C1)* 0.000 description 1
- MBIZXFATKUQOOA-UHFFFAOYSA-N 1,3,4-thiadiazole Chemical compound C1=NN=CS1 MBIZXFATKUQOOA-UHFFFAOYSA-N 0.000 description 1
- KNBDJFUYNPDJIO-UHFFFAOYSA-N 2,6-dichloro-n-(5-phenyl-1,3,4-thiadiazol-2-yl)benzamide Chemical compound ClC1=CC=CC(Cl)=C1C(=O)NC1=NN=C(C=2C=CC=CC=2)S1 KNBDJFUYNPDJIO-UHFFFAOYSA-N 0.000 description 1
- XFTZPNZHQALXGZ-UHFFFAOYSA-N 2,6-dichloro-n-[5-(4-fluorophenyl)-1,3,4-thiadiazol-2-yl]benzamide Chemical compound C1=CC(F)=CC=C1C(S1)=NN=C1NC(=O)C1=C(Cl)C=CC=C1Cl XFTZPNZHQALXGZ-UHFFFAOYSA-N 0.000 description 1
- IFLZKWPGEQADRM-UHFFFAOYSA-N 2,6-dichloro-n-[5-[4-(trifluoromethyl)phenyl]-1,3,4-thiadiazol-2-yl]benzamide Chemical compound C1=CC(C(F)(F)F)=CC=C1C(S1)=NN=C1NC(=O)C1=C(Cl)C=CC=C1Cl IFLZKWPGEQADRM-UHFFFAOYSA-N 0.000 description 1
- JBLIDPPHFGWTKU-UHFFFAOYSA-N 2,6-dichlorobenzoyl chloride Chemical compound ClC(=O)C1=C(Cl)C=CC=C1Cl JBLIDPPHFGWTKU-UHFFFAOYSA-N 0.000 description 1
- QMXJDBVFOJMGQO-UHFFFAOYSA-N 2,6-dimethoxy-n-(5-naphthalen-1-yl-1,3,4-thiadiazol-2-yl)benzamide Chemical compound COC1=CC=CC(OC)=C1C(=O)NC1=NN=C(C=2C3=CC=CC=C3C=CC=2)S1 QMXJDBVFOJMGQO-UHFFFAOYSA-N 0.000 description 1
- CCWJGLHSHGEBMJ-UHFFFAOYSA-N 2,6-dimethoxy-n-(5-naphthalen-2-yl-1,3,4-thiadiazol-2-yl)benzamide Chemical compound COC1=CC=CC(OC)=C1C(=O)NC1=NN=C(C=2C=C3C=CC=CC3=CC=2)S1 CCWJGLHSHGEBMJ-UHFFFAOYSA-N 0.000 description 1
- PTXROMVBVOJJJG-UHFFFAOYSA-N 2,6-dimethoxy-n-(5-phenyl-1,3,4-thiadiazol-2-yl)benzamide Chemical compound COC1=CC=CC(OC)=C1C(=O)NC1=NN=C(C=2C=CC=CC=2)S1 PTXROMVBVOJJJG-UHFFFAOYSA-N 0.000 description 1
- ARBUOWJKHXRXIT-UHFFFAOYSA-N 2,6-dimethoxy-n-(5-quinolin-3-yl-1,3,4-thiadiazol-2-yl)benzamide Chemical compound COC1=CC=CC(OC)=C1C(=O)NC1=NN=C(C=2C=C3C=CC=CC3=NC=2)S1 ARBUOWJKHXRXIT-UHFFFAOYSA-N 0.000 description 1
- LFAHWVNNGABFOH-UHFFFAOYSA-N 2,6-dimethoxy-n-(5-thiophen-2-yl-1,3,4-thiadiazol-2-yl)benzamide Chemical compound COC1=CC=CC(OC)=C1C(=O)NC1=NN=C(C=2SC=CC=2)S1 LFAHWVNNGABFOH-UHFFFAOYSA-N 0.000 description 1
- PXJKNHXTILDQAN-UHFFFAOYSA-N 2,6-dimethoxy-n-(5-thiophen-3-yl-1,3,4-thiadiazol-2-yl)benzamide Chemical compound COC1=CC=CC(OC)=C1C(=O)NC1=NN=C(C2=CSC=C2)S1 PXJKNHXTILDQAN-UHFFFAOYSA-N 0.000 description 1
- YENZKZMWFQLRFU-UHFFFAOYSA-N 2,6-dimethoxy-n-[(pyridine-4-carbonylamino)carbamothioyl]benzamide Chemical compound COC1=CC=CC(OC)=C1C(=O)NC(=S)NNC(=O)C1=CC=NC=C1 YENZKZMWFQLRFU-UHFFFAOYSA-N 0.000 description 1
- RFTLOARXRMBJOM-UHFFFAOYSA-N 2,6-dimethoxy-n-[(quinoline-2-carbonylamino)carbamothioyl]benzamide Chemical compound COC1=CC=CC(OC)=C1C(=O)NC(=S)NNC(=O)C1=CC=C(C=CC=C2)C2=N1 RFTLOARXRMBJOM-UHFFFAOYSA-N 0.000 description 1
- CBRJAKCZGIBCKD-UHFFFAOYSA-N 2,6-dimethoxy-n-[(quinoline-3-carbonylamino)carbamothioyl]benzamide Chemical compound COC1=CC=CC(OC)=C1C(=O)NC(=S)NNC(=O)C1=CN=C(C=CC=C2)C2=C1 CBRJAKCZGIBCKD-UHFFFAOYSA-N 0.000 description 1
- FSCCDQRGDDGRKR-UHFFFAOYSA-N 2,6-dimethoxy-n-[5-(1,2-oxazol-3-yl)-1,3,4-thiadiazol-2-yl]benzamide Chemical compound COC1=CC=CC(OC)=C1C(=O)NC1=NN=C(C2=NOC=C2)S1 FSCCDQRGDDGRKR-UHFFFAOYSA-N 0.000 description 1
- LGZUCKXVPQKYAE-UHFFFAOYSA-N 2,6-dimethoxy-n-[5-(4-methoxyphenyl)-1,3,4-thiadiazol-2-yl]benzamide Chemical compound C1=CC(OC)=CC=C1C(S1)=NN=C1NC(=O)C1=C(OC)C=CC=C1OC LGZUCKXVPQKYAE-UHFFFAOYSA-N 0.000 description 1
- UWEXURYTNACCOD-UHFFFAOYSA-N 2,6-dimethoxy-n-[5-(4-methylphenyl)-1,3,4-thiadiazol-2-yl]benzamide Chemical compound COC1=CC=CC(OC)=C1C(=O)NC1=NN=C(C=2C=CC(C)=CC=2)S1 UWEXURYTNACCOD-UHFFFAOYSA-N 0.000 description 1
- ANXSTMYCQGFSCQ-UHFFFAOYSA-N 2,6-dimethoxy-n-[5-(4-nitrophenyl)-1,3,4-thiadiazol-2-yl]benzamide Chemical compound COC1=CC=CC(OC)=C1C(=O)NC1=NN=C(C=2C=CC(=CC=2)[N+]([O-])=O)S1 ANXSTMYCQGFSCQ-UHFFFAOYSA-N 0.000 description 1
- AJPJPVIPTQYYDT-UHFFFAOYSA-N 2,6-dimethoxy-n-[5-(4-phenylphenyl)-1,3,4-thiadiazol-2-yl]benzamide Chemical compound COC1=CC=CC(OC)=C1C(=O)NC1=NN=C(C=2C=CC(=CC=2)C=2C=CC=CC=2)S1 AJPJPVIPTQYYDT-UHFFFAOYSA-N 0.000 description 1
- MIGOSJLALGNVDQ-UHFFFAOYSA-N 2,6-dimethyl-n-(5-naphthalen-2-yl-1,3,4-thiadiazol-2-yl)benzamide Chemical compound CC1=CC=CC(C)=C1C(=O)NC1=NN=C(C=2C=C3C=CC=CC3=CC=2)S1 MIGOSJLALGNVDQ-UHFFFAOYSA-N 0.000 description 1
- FTALFBSNZDSPPK-UHFFFAOYSA-N 2,6-dimethyl-n-(5-phenyl-1,3,4-thiadiazol-2-yl)benzamide Chemical compound CC1=CC=CC(C)=C1C(=O)NC1=NN=C(C=2C=CC=CC=2)S1 FTALFBSNZDSPPK-UHFFFAOYSA-N 0.000 description 1
- ZBCCELGDWWNQOX-UHFFFAOYSA-N 2-chloro-n-[5-(4-chlorophenyl)-1,3,4-thiadiazol-2-yl]-6-methylbenzamide Chemical compound CC1=CC=CC(Cl)=C1C(=O)NC1=NN=C(C=2C=CC(Cl)=CC=2)S1 ZBCCELGDWWNQOX-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- 229940093475 2-ethoxyethanol Drugs 0.000 description 1
- FQUOYEHJJRUIQC-UHFFFAOYSA-N 3-(5-amino-1,3,4-thiadiazol-2-yl)phenol Chemical compound S1C(N)=NN=C1C1=CC=CC(O)=C1 FQUOYEHJJRUIQC-UHFFFAOYSA-N 0.000 description 1
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- AVPYQKSLYISFPO-UHFFFAOYSA-N 4-chlorobenzaldehyde Chemical compound ClC1=CC=C(C=O)C=C1 AVPYQKSLYISFPO-UHFFFAOYSA-N 0.000 description 1
- PKBGHORNUFQAAW-UHFFFAOYSA-N 4-chlorobenzohydrazide Chemical compound NNC(=O)C1=CC=C(Cl)C=C1 PKBGHORNUFQAAW-UHFFFAOYSA-N 0.000 description 1
- ZMZGIVVRBMFZSG-UHFFFAOYSA-N 4-hydroxybenzohydrazide Chemical compound NNC(=O)C1=CC=C(O)C=C1 ZMZGIVVRBMFZSG-UHFFFAOYSA-N 0.000 description 1
- RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 description 1
- 241001136265 Agriotes Species 0.000 description 1
- 241000254175 Anthonomus grandis Species 0.000 description 1
- 241000238657 Blattella germanica Species 0.000 description 1
- WJTOKZFEGHBJPW-UHFFFAOYSA-N CC1=C2C(=CC=C1)C=C(O2)C3=NN=C(S3)NC(=O)C4=C(C=CC=C4OC)OC Chemical compound CC1=C2C(=CC=C1)C=C(O2)C3=NN=C(S3)NC(=O)C4=C(C=CC=C4OC)OC WJTOKZFEGHBJPW-UHFFFAOYSA-N 0.000 description 1
- 241000604356 Chamaepsila rosae Species 0.000 description 1
- 241000532667 Conotrachelus Species 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- 241001340508 Crambus Species 0.000 description 1
- 241001635274 Cydia pomonella Species 0.000 description 1
- 241001414892 Delia radicum Species 0.000 description 1
- 241000255925 Diptera Species 0.000 description 1
- 241001301805 Epilachna Species 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical class C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- 241001585293 Euxoa Species 0.000 description 1
- 241000257232 Haematobia irritans Species 0.000 description 1
- 241000255967 Helicoverpa zea Species 0.000 description 1
- 241001351414 Hellula Species 0.000 description 1
- 241001508566 Hypera postica Species 0.000 description 1
- 241000258916 Leptinotarsa decemlineata Species 0.000 description 1
- 229920001732 Lignosulfonate Polymers 0.000 description 1
- 241000920471 Lucilia caesar Species 0.000 description 1
- 241001177141 Lyctinae Species 0.000 description 1
- 241000255682 Malacosoma americanum Species 0.000 description 1
- 241000257159 Musca domestica Species 0.000 description 1
- XMLBSPBPBQMZKM-UHFFFAOYSA-N N-[5-[3-(4-chlorophenyl)phenyl]-1,3,4-thiadiazol-2-yl]-2,6-dimethoxybenzamide Chemical compound COC1=CC=CC(OC)=C1C(=O)NC1=NN=C(C=2C=C(C=CC=2)C=2C=CC(Cl)=CC=2)S1 XMLBSPBPBQMZKM-UHFFFAOYSA-N 0.000 description 1
- 241000798111 Nodonota Species 0.000 description 1
- 241000238814 Orthoptera Species 0.000 description 1
- 241001160353 Oulema melanopus Species 0.000 description 1
- 241000595629 Plodia interpunctella Species 0.000 description 1
- 241000382353 Pupa Species 0.000 description 1
- KHPCPRHQVVSZAH-HUOMCSJISA-N Rosin Natural products O(C/C=C/c1ccccc1)[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 KHPCPRHQVVSZAH-HUOMCSJISA-N 0.000 description 1
- 241000254152 Sitophilus oryzae Species 0.000 description 1
- 241000256251 Spodoptera frugiperda Species 0.000 description 1
- 241001494115 Stomoxys calcitrans Species 0.000 description 1
- 241000333702 Thyridopteryx ephemeraeformis Species 0.000 description 1
- 241000254112 Tribolium confusum Species 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- 241000607479 Yersinia pestis Species 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 150000008051 alkyl sulfates Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 235000021336 beef liver Nutrition 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
- 150000001555 benzenes Chemical class 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 230000008033 biological extinction Effects 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- CRPOUZQWHJYTMS-UHFFFAOYSA-N dialuminum;magnesium;disilicate Chemical compound [Mg+2].[Al+3].[Al+3].[O-][Si]([O-])([O-])[O-].[O-][Si]([O-])([O-])[O-] CRPOUZQWHJYTMS-UHFFFAOYSA-N 0.000 description 1
- 150000004816 dichlorobenzenes Chemical class 0.000 description 1
- YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 1
- 230000008034 disappearance Effects 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 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 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 125000001072 heteroaryl group Chemical group 0.000 description 1
- 235000012907 honey Nutrition 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 239000011872 intimate mixture Substances 0.000 description 1
- 125000002346 iodo group Chemical group I* 0.000 description 1
- QRXWMOHMRWLFEY-UHFFFAOYSA-N isoniazide Chemical compound NNC(=O)C1=CC=NC=C1 QRXWMOHMRWLFEY-UHFFFAOYSA-N 0.000 description 1
- 230000001418 larval effect Effects 0.000 description 1
- 239000002267 larvicidal agent Substances 0.000 description 1
- 235000019357 lignosulphonate Nutrition 0.000 description 1
- HQRPHMAXFVUBJX-UHFFFAOYSA-M lithium;hydrogen carbonate Chemical compound [Li+].OC([O-])=O HQRPHMAXFVUBJX-UHFFFAOYSA-M 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000004452 microanalysis Methods 0.000 description 1
- RWOUBULBQYRRNL-UHFFFAOYSA-N n-(1,3,4-thiadiazol-2-yl)benzamide Chemical class C=1C=CC=CC=1C(=O)NC1=NN=CS1 RWOUBULBQYRRNL-UHFFFAOYSA-N 0.000 description 1
- WHLGXCDAKQSJGK-UHFFFAOYSA-N n-[(1,3-benzothiazole-2-carbonylamino)carbamothioyl]-2,6-dimethoxybenzamide Chemical compound COC1=CC=CC(OC)=C1C(=O)NC(=S)NNC(=O)C1=NC2=CC=CC=C2S1 WHLGXCDAKQSJGK-UHFFFAOYSA-N 0.000 description 1
- SMLKBGQBMKBBOJ-UHFFFAOYSA-N n-[5-(2,4-dibromophenyl)-1,3,4-thiadiazol-2-yl]-2,6-dimethylbenzamide Chemical compound CC1=CC=CC(C)=C1C(=O)NC1=NN=C(C=2C(=CC(Br)=CC=2)Br)S1 SMLKBGQBMKBBOJ-UHFFFAOYSA-N 0.000 description 1
- HINDJTRJOLKRDX-UHFFFAOYSA-N n-[5-(2,4-dichlorophenyl)-1,3,4-thiadiazol-2-yl]-2,6-dimethoxybenzamide Chemical compound COC1=CC=CC(OC)=C1C(=O)NC1=NN=C(C=2C(=CC(Cl)=CC=2)Cl)S1 HINDJTRJOLKRDX-UHFFFAOYSA-N 0.000 description 1
- DBRBFFVKHRHWGW-UHFFFAOYSA-N n-[5-(2-bromophenyl)-1,3,4-thiadiazol-2-yl]-2-methoxy-6-methylbenzamide Chemical compound COC1=CC=CC(C)=C1C(=O)NC1=NN=C(C=2C(=CC=CC=2)Br)S1 DBRBFFVKHRHWGW-UHFFFAOYSA-N 0.000 description 1
- ODAHYKZHJYPFRG-UHFFFAOYSA-N n-[5-(2-fluorophenyl)-1,3,4-thiadiazol-2-yl]-2,6-dimethoxybenzamide Chemical compound COC1=CC=CC(OC)=C1C(=O)NC1=NN=C(C=2C(=CC=CC=2)F)S1 ODAHYKZHJYPFRG-UHFFFAOYSA-N 0.000 description 1
- PFVGJZYJPMMINZ-UHFFFAOYSA-N n-[5-(3,4-dibromophenyl)-1,3,4-thiadiazol-2-yl]-2,6-dimethylbenzamide Chemical compound CC1=CC=CC(C)=C1C(=O)NC1=NN=C(C=2C=C(Br)C(Br)=CC=2)S1 PFVGJZYJPMMINZ-UHFFFAOYSA-N 0.000 description 1
- WZFGHTXEKNROHQ-UHFFFAOYSA-N n-[5-(3,4-dichlorophenyl)-1,3,4-thiadiazol-2-yl]-2,6-dimethoxybenzamide Chemical compound COC1=CC=CC(OC)=C1C(=O)NC1=NN=C(C=2C=C(Cl)C(Cl)=CC=2)S1 WZFGHTXEKNROHQ-UHFFFAOYSA-N 0.000 description 1
- BFFRRYVNIYZNPQ-UHFFFAOYSA-N n-[5-(3,4-dichlorophenyl)-1,3,4-thiadiazol-2-yl]-2,6-dimethylbenzamide Chemical compound CC1=CC=CC(C)=C1C(=O)NC1=NN=C(C=2C=C(Cl)C(Cl)=CC=2)S1 BFFRRYVNIYZNPQ-UHFFFAOYSA-N 0.000 description 1
- SGPMKLJYEYXYES-UHFFFAOYSA-N n-[5-(3,4-difluorophenyl)-1,3,4-thiadiazol-2-yl]-2,6-dimethoxybenzamide Chemical compound COC1=CC=CC(OC)=C1C(=O)NC1=NN=C(C=2C=C(F)C(F)=CC=2)S1 SGPMKLJYEYXYES-UHFFFAOYSA-N 0.000 description 1
- OLERTNMOYYQQIK-UHFFFAOYSA-N n-[5-(3,5-dibromophenyl)-1,3,4-thiadiazol-2-yl]-2,6-dimethoxybenzamide Chemical compound COC1=CC=CC(OC)=C1C(=O)NC1=NN=C(C=2C=C(Br)C=C(Br)C=2)S1 OLERTNMOYYQQIK-UHFFFAOYSA-N 0.000 description 1
- RNIOBNUCZBEWTF-UHFFFAOYSA-N n-[5-(3,5-dichlorophenyl)-1,3,4-thiadiazol-2-yl]-2,6-dimethoxybenzamide Chemical compound COC1=CC=CC(OC)=C1C(=O)NC1=NN=C(C=2C=C(Cl)C=C(Cl)C=2)S1 RNIOBNUCZBEWTF-UHFFFAOYSA-N 0.000 description 1
- DBYYCHWFHISJKN-UHFFFAOYSA-N n-[5-(3,5-difluorophenyl)-1,3,4-thiadiazol-2-yl]-2,6-dimethylbenzamide Chemical compound CC1=CC=CC(C)=C1C(=O)NC1=NN=C(C=2C=C(F)C=C(F)C=2)S1 DBYYCHWFHISJKN-UHFFFAOYSA-N 0.000 description 1
- PTLRDYUCFDMWBE-UHFFFAOYSA-N n-[5-(3-bromo-4-fluorophenyl)-1,3,4-thiadiazol-2-yl]-2-methoxy-6-methylbenzamide Chemical compound COC1=CC=CC(C)=C1C(=O)NC1=NN=C(C=2C=C(Br)C(F)=CC=2)S1 PTLRDYUCFDMWBE-UHFFFAOYSA-N 0.000 description 1
- PPIVMOGRCKITDR-UHFFFAOYSA-N n-[5-(3-bromo-5-fluorophenyl)-1,3,4-thiadiazol-2-yl]-2-methoxy-6-methylbenzamide Chemical compound COC1=CC=CC(C)=C1C(=O)NC1=NN=C(C=2C=C(Br)C=C(F)C=2)S1 PPIVMOGRCKITDR-UHFFFAOYSA-N 0.000 description 1
- KPKLDUMJBZUDES-UHFFFAOYSA-N n-[5-(3-bromophenyl)-1,3,4-thiadiazol-2-yl]-2-fluoro-6-methylbenzamide Chemical compound CC1=CC=CC(F)=C1C(=O)NC1=NN=C(C=2C=C(Br)C=CC=2)S1 KPKLDUMJBZUDES-UHFFFAOYSA-N 0.000 description 1
- UDVOUZHVXYUTBK-UHFFFAOYSA-N n-[5-(3-chlorophenyl)-1,3,4-thiadiazol-2-yl]-2,6-dimethylbenzamide Chemical compound CC1=CC=CC(C)=C1C(=O)NC1=NN=C(C=2C=C(Cl)C=CC=2)S1 UDVOUZHVXYUTBK-UHFFFAOYSA-N 0.000 description 1
- XMLJBOLNHAWVDM-UHFFFAOYSA-N n-[5-(3-fluorophenyl)-1,3,4-thiadiazol-2-yl]-2,6-dimethoxybenzamide Chemical compound COC1=CC=CC(OC)=C1C(=O)NC1=NN=C(C=2C=C(F)C=CC=2)S1 XMLJBOLNHAWVDM-UHFFFAOYSA-N 0.000 description 1
- XKVPATRGDAQPCT-UHFFFAOYSA-N n-[5-(4-aminophenyl)-1,3,4-thiadiazol-2-yl]-2,6-dimethoxybenzamide Chemical compound COC1=CC=CC(OC)=C1C(=O)NC1=NN=C(C=2C=CC(N)=CC=2)S1 XKVPATRGDAQPCT-UHFFFAOYSA-N 0.000 description 1
- QFFYCAPRNXSAIS-UHFFFAOYSA-N n-[5-(4-bromo-2-chlorophenyl)-1,3,4-thiadiazol-2-yl]-2-methoxybenzamide Chemical compound COC1=CC=CC=C1C(=O)NC1=NN=C(C=2C(=CC(Br)=CC=2)Cl)S1 QFFYCAPRNXSAIS-UHFFFAOYSA-N 0.000 description 1
- QUSWMFJAUYWIDH-UHFFFAOYSA-N n-[5-(4-bromophenyl)-1,3,4-thiadiazol-2-yl]-2,6-dichlorobenzamide Chemical compound ClC1=CC=CC(Cl)=C1C(=O)NC1=NN=C(C=2C=CC(Br)=CC=2)S1 QUSWMFJAUYWIDH-UHFFFAOYSA-N 0.000 description 1
- ALSJVSPWCXFZHU-UHFFFAOYSA-N n-[5-(4-bromophenyl)-1,3,4-thiadiazol-2-yl]-2,6-dimethoxybenzamide Chemical compound COC1=CC=CC(OC)=C1C(=O)NC1=NN=C(C=2C=CC(Br)=CC=2)S1 ALSJVSPWCXFZHU-UHFFFAOYSA-N 0.000 description 1
- IKPYSFSXRPSQSG-UHFFFAOYSA-N n-[5-(4-bromophenyl)-1,3,4-thiadiazol-2-yl]-2,6-dimethylbenzamide Chemical compound CC1=CC=CC(C)=C1C(=O)NC1=NN=C(C=2C=CC(Br)=CC=2)S1 IKPYSFSXRPSQSG-UHFFFAOYSA-N 0.000 description 1
- YSFPDARVNXQRSB-UHFFFAOYSA-N n-[5-(4-chlorophenyl)-1,3,4-thiadiazol-2-yl]-2,6-difluorobenzamide Chemical compound FC1=CC=CC(F)=C1C(=O)NC1=NN=C(C=2C=CC(Cl)=CC=2)S1 YSFPDARVNXQRSB-UHFFFAOYSA-N 0.000 description 1
- OEZKKHSTGOOROK-UHFFFAOYSA-N n-[5-(4-chlorophenyl)-1,3,4-thiadiazol-2-yl]-2-methoxybenzamide Chemical compound COC1=CC=CC=C1C(=O)NC1=NN=C(C=2C=CC(Cl)=CC=2)S1 OEZKKHSTGOOROK-UHFFFAOYSA-N 0.000 description 1
- YKBSZNVWCSNIIE-UHFFFAOYSA-N n-[5-(4-cyanophenyl)-1,3,4-thiadiazol-2-yl]-2,6-dimethoxybenzamide Chemical compound COC1=CC=CC(OC)=C1C(=O)NC1=NN=C(C=2C=CC(=CC=2)C#N)S1 YKBSZNVWCSNIIE-UHFFFAOYSA-N 0.000 description 1
- FGUWFAJEAITMOE-UHFFFAOYSA-N n-[5-(4-iodophenyl)-1,3,4-thiadiazol-2-yl]-2,6-dimethoxybenzamide Chemical compound COC1=CC=CC(OC)=C1C(=O)NC1=NN=C(C=2C=CC(I)=CC=2)S1 FGUWFAJEAITMOE-UHFFFAOYSA-N 0.000 description 1
- HOXLEPUZGWCQQT-UHFFFAOYSA-N n-[5-(5-bromofuran-2-yl)-1,3,4-thiadiazol-2-yl]-2,6-dimethoxybenzamide Chemical compound COC1=CC=CC(OC)=C1C(=O)NC1=NN=C(C=2OC(Br)=CC=2)S1 HOXLEPUZGWCQQT-UHFFFAOYSA-N 0.000 description 1
- MEVPOXFINPSUJK-UHFFFAOYSA-N n-[5-(5-bromopyridin-3-yl)-1,3,4-thiadiazol-2-yl]-2,6-dimethoxybenzamide Chemical compound COC1=CC=CC(OC)=C1C(=O)NC1=NN=C(C=2C=C(Br)C=NC=2)S1 MEVPOXFINPSUJK-UHFFFAOYSA-N 0.000 description 1
- RBRFHHFWEGKNIV-UHFFFAOYSA-N n-[5-(5-chloro-1-benzothiophen-2-yl)-1,3,4-thiadiazol-2-yl]-2,6-dimethoxybenzamide Chemical compound COC1=CC=CC(OC)=C1C(=O)NC1=NN=C(C=2SC3=CC=C(Cl)C=C3C=2)S1 RBRFHHFWEGKNIV-UHFFFAOYSA-N 0.000 description 1
- BASBXACYHCTPOS-UHFFFAOYSA-N n-[5-(5-chlorothiophen-2-yl)-1,3,4-thiadiazol-2-yl]-2,6-dimethoxybenzamide Chemical compound COC1=CC=CC(OC)=C1C(=O)NC1=NN=C(C=2SC(Cl)=CC=2)S1 BASBXACYHCTPOS-UHFFFAOYSA-N 0.000 description 1
- NXNCWUXMOCSYKO-UHFFFAOYSA-N n-[5-(furan-2-yl)-1,3,4-thiadiazol-2-yl]-2,6-dimethoxybenzamide Chemical compound COC1=CC=CC(OC)=C1C(=O)NC1=NN=C(C=2OC=CC=2)S1 NXNCWUXMOCSYKO-UHFFFAOYSA-N 0.000 description 1
- ICFAAPMKVFCZIY-UHFFFAOYSA-N n-[5-(furan-3-yl)-1,3,4-thiadiazol-2-yl]-2,6-dimethoxybenzamide Chemical compound COC1=CC=CC(OC)=C1C(=O)NC1=NN=C(C2=COC=C2)S1 ICFAAPMKVFCZIY-UHFFFAOYSA-N 0.000 description 1
- UZTIUDUNSRTFEX-UHFFFAOYSA-N n-[5-[3,5-bis(trifluoromethyl)phenyl]-1,3,4-thiadiazol-2-yl]-2,6-dimethylbenzamide Chemical compound CC1=CC=CC(C)=C1C(=O)NC1=NN=C(C=2C=C(C=C(C=2)C(F)(F)F)C(F)(F)F)S1 UZTIUDUNSRTFEX-UHFFFAOYSA-N 0.000 description 1
- VHUOSTWNIKRCKH-UHFFFAOYSA-N n-[5-[4-(2-chlorophenyl)phenyl]-1,3,4-thiadiazol-2-yl]-2,6-dimethoxybenzamide Chemical compound COC1=CC=CC(OC)=C1C(=O)NC1=NN=C(C=2C=CC(=CC=2)C=2C(=CC=CC=2)Cl)S1 VHUOSTWNIKRCKH-UHFFFAOYSA-N 0.000 description 1
- UWCZKJXPRHYJRS-UHFFFAOYSA-N n-[5-[4-(3-bromophenyl)phenyl]-1,3,4-thiadiazol-2-yl]-2,6-dimethoxybenzamide Chemical compound COC1=CC=CC(OC)=C1C(=O)NC1=NN=C(C=2C=CC(=CC=2)C=2C=C(Br)C=CC=2)S1 UWCZKJXPRHYJRS-UHFFFAOYSA-N 0.000 description 1
- NNDCFPJGPAGPQT-UHFFFAOYSA-N n-[5-[4-(4-bromophenyl)phenyl]-1,3,4-thiadiazol-2-yl]-2,6-dimethoxybenzamide Chemical compound COC1=CC=CC(OC)=C1C(=O)NC1=NN=C(C=2C=CC(=CC=2)C=2C=CC(Br)=CC=2)S1 NNDCFPJGPAGPQT-UHFFFAOYSA-N 0.000 description 1
- JCGFIVJWNVAHHI-UHFFFAOYSA-N n-[5-[4-(4-chlorophenyl)phenyl]-1,3,4-thiadiazol-2-yl]-2,6-dimethoxybenzamide Chemical compound COC1=CC=CC(OC)=C1C(=O)NC1=NN=C(C=2C=CC(=CC=2)C=2C=CC(Cl)=CC=2)S1 JCGFIVJWNVAHHI-UHFFFAOYSA-N 0.000 description 1
- BYFVEUMFZFHENY-UHFFFAOYSA-N n-[5-[4-(4-fluorophenyl)phenyl]-1,3,4-thiadiazol-2-yl]-2,6-dimethoxybenzamide Chemical compound COC1=CC=CC(OC)=C1C(=O)NC1=NN=C(C=2C=CC(=CC=2)C=2C=CC(F)=CC=2)S1 BYFVEUMFZFHENY-UHFFFAOYSA-N 0.000 description 1
- NRYXBZDROVNLPQ-UHFFFAOYSA-N n-[[(2-chlorobenzoyl)amino]carbamothioyl]-2,6-dimethoxybenzamide Chemical compound COC1=CC=CC(OC)=C1C(=O)NC(=S)NNC(=O)C1=CC=CC=C1Cl NRYXBZDROVNLPQ-UHFFFAOYSA-N 0.000 description 1
- BWBYZMQNWMKXIK-UHFFFAOYSA-N n-[[(5-chloro-1-benzothiophene-2-carbonyl)amino]carbamothioyl]-2,6-dimethoxybenzamide Chemical compound COC1=CC=CC(OC)=C1C(=O)NC(=S)NNC(=O)C1=CC2=CC(Cl)=CC=C2S1 BWBYZMQNWMKXIK-UHFFFAOYSA-N 0.000 description 1
- 125000006501 nitrophenyl group Chemical group 0.000 description 1
- 229910000510 noble metal Inorganic materials 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000000123 paper Substances 0.000 description 1
- 244000045947 parasite Species 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- BGUWFUQJCDRPTL-UHFFFAOYSA-N pyridine-4-carbaldehyde Chemical compound O=CC1=CC=NC=C1 BGUWFUQJCDRPTL-UHFFFAOYSA-N 0.000 description 1
- 229910052903 pyrophyllite Inorganic materials 0.000 description 1
- JTDPJYXDDYUJBS-UHFFFAOYSA-N quinoline-2-carbohydrazide Chemical compound C1=CC=CC2=NC(C(=O)NN)=CC=C21 JTDPJYXDDYUJBS-UHFFFAOYSA-N 0.000 description 1
- ZARLOFXXUFNOHB-UHFFFAOYSA-N quinoline-3-carbohydrazide Chemical compound C1=CC=CC2=CC(C(=O)NN)=CN=C21 ZARLOFXXUFNOHB-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 1
- 150000004867 thiadiazoles Chemical group 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 description 1
- 235000019195 vitamin supplement Nutrition 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 150000003738 xylenes Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
- C07D285/01—Five-membered rings
- C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
- C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
- C07D285/12—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles
- C07D285/125—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles with oxygen, sulfur or nitrogen atoms, directly attached to ring carbon atoms, the nitrogen atoms not forming part of a nitro radical
- C07D285/135—Nitrogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
- Plural Heterocyclic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US65655276A | 1976-02-09 | 1976-02-09 | |
| US74016676A | 1976-11-10 | 1976-11-10 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1571422A true GB1571422A (en) | 1980-07-16 |
Family
ID=27097215
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB4389/77A Expired GB1571422A (en) | 1976-02-09 | 1977-02-03 | Benzamides and their use as insecticides |
Country Status (30)
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2107054A1 (en) * | 2008-04-01 | 2009-10-07 | Università Degli Studi Di Milano - Bicocca | Antiproliferative compounds and therapeutic uses thereof |
| EP1983980A4 (en) * | 2006-01-25 | 2010-05-05 | Synta Pharmaceuticals Corp | THIAZOL AND THIADIAZOL COMPOUNDS FOR USES IN RELATION TO INFLAMMATION AND IMMUNITY |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2011128304A2 (de) | 2010-04-16 | 2011-10-20 | Bayer Cropscience Ag | Neue heterocyclische verbindungen als schädlingsbekämpfungsmittel |
| WO2012030681A1 (en) * | 2010-08-31 | 2012-03-08 | Dow Agrosciences Llc | Pesticidal compositions |
| JPWO2012121168A1 (ja) * | 2011-03-04 | 2014-07-17 | 国立大学法人京都大学 | キナーゼ阻害剤 |
| WO2014060381A1 (de) | 2012-10-18 | 2014-04-24 | Bayer Cropscience Ag | Heterocyclische verbindungen als schädlingsbekämpfungsmittel |
| PT3113618T (pt) * | 2014-03-06 | 2018-11-20 | Bayer Cropscience Ag | Compostos heterocíclicos como pesticidas |
| EP3555089A1 (en) * | 2016-12-16 | 2019-10-23 | Bayer CropScience Aktiengesellschaft | Thiadiazole derivatives as pesticides |
| CA3047638A1 (en) * | 2016-12-22 | 2018-06-28 | Bayer Cropscience Aktiengesellschaft | Substituted heteroaryl pyrrolones and salts thereof and use thereof as herbicidal active substances |
| CN109456283B (zh) * | 2018-12-13 | 2023-03-28 | 贵州大学 | 含1,3,4-噻二唑硫醚(砜)的2-(三氟甲基)苯甲酰胺类衍生物、其制备及应用 |
-
1976
- 1976-12-18 GR GR52438A patent/GR65893B/el unknown
- 1976-12-20 IE IE2783/76A patent/IE44573B1/en unknown
- 1976-12-21 NZ NZ182937A patent/NZ182937A/xx unknown
- 1976-12-22 CA CA268,463A patent/CA1077041A/en not_active Expired
- 1976-12-23 IL IL51149A patent/IL51149A/xx unknown
-
1977
- 1977-01-11 AR AR266147A patent/AR221204A1/es active
- 1977-01-25 SE SE7700778A patent/SE412063B/xx unknown
- 1977-01-26 BR BR7700471A patent/BR7700471A/pt unknown
- 1977-01-27 ES ES455409A patent/ES455409A1/es not_active Expired
- 1977-02-01 SU SU772446348A patent/SU706023A3/ru active
- 1977-02-02 DE DE19772704288 patent/DE2704288A1/de not_active Ceased
- 1977-02-02 NL NL7701059A patent/NL7701059A/xx not_active Application Discontinuation
- 1977-02-03 BG BG037894A patent/BG28987A4/xx unknown
- 1977-02-03 BG BG037893A patent/BG28986A4/xx unknown
- 1977-02-03 BG BG035326A patent/BG28236A3/xx unknown
- 1977-02-03 GB GB4389/77A patent/GB1571422A/en not_active Expired
- 1977-02-04 PT PT66158A patent/PT66158A/pt unknown
- 1977-02-07 HU HU77EI725A patent/HU179458B/hu unknown
- 1977-02-07 AU AU22026/77A patent/AU505649B2/en not_active Expired
- 1977-02-07 CH CH146977A patent/CH631603A5/de not_active IP Right Cessation
- 1977-02-07 DK DK50677A patent/DK50677A/da not_active Application Discontinuation
- 1977-02-08 IT IT20057/77A patent/IT1078058B/it active
- 1977-02-08 AT AT81877A patent/AT362192B/de not_active IP Right Cessation
- 1977-02-08 CS CS77822A patent/CS198217B2/cs unknown
- 1977-02-09 JP JP1404977A patent/JPS52105173A/ja active Pending
- 1977-02-09 PL PL1977220785A patent/PL113231B1/pl unknown
- 1977-02-09 DD DD7700197305A patent/DD130038A5/xx unknown
- 1977-02-09 FR FR7703603A patent/FR2340312A1/fr active Granted
- 1977-02-09 DD DD77204378A patent/DD135032A5/xx unknown
- 1977-02-09 PL PL1977195892A patent/PL112645B1/pl unknown
- 1977-02-13 RO RO7796600A patent/RO76588A/ro unknown
-
1978
- 1978-02-16 ES ES467061A patent/ES467061A1/es not_active Expired
-
1979
- 1979-02-17 RO RO7996599A patent/RO76587A/ro unknown
-
1981
- 1981-06-02 KE KE3131A patent/KE3131A/xx unknown
- 1981-06-18 HK HK270/81A patent/HK27081A/xx unknown
-
1982
- 1982-12-30 MY MY38/82A patent/MY8200038A/xx unknown
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1983980A4 (en) * | 2006-01-25 | 2010-05-05 | Synta Pharmaceuticals Corp | THIAZOL AND THIADIAZOL COMPOUNDS FOR USES IN RELATION TO INFLAMMATION AND IMMUNITY |
| AU2007208225B2 (en) * | 2006-01-25 | 2013-05-02 | Synta Pharmaceuticals Corp. | Thiazole and thiadiazole compounds for inflammation and immune-related uses |
| US8455658B2 (en) | 2006-01-25 | 2013-06-04 | Synta Pharmaceuticals Corp. | Thiazole and thiadiazole compounds for inflammation and immune-related uses |
| EP2107054A1 (en) * | 2008-04-01 | 2009-10-07 | Università Degli Studi Di Milano - Bicocca | Antiproliferative compounds and therapeutic uses thereof |
| WO2009121535A3 (en) * | 2008-04-01 | 2010-01-07 | Universita`Degli Studi Di Milano - Bicocca | Antiproliferative compounds and therapeutic uses thereof |
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US4141984A (en) | N-(1,3,4-thiadiazol-2-yl)benzamides | |
| JPH05386B2 (enrdf_load_stackoverflow) | ||
| JPS6368567A (ja) | 新規複素環式化合物及び殺虫剤 | |
| US4514406A (en) | Oxime ethers and their use | |
| CA1164871A (en) | Isoxazolylbenzamides | |
| GB1571422A (en) | Benzamides and their use as insecticides | |
| US6235762B1 (en) | 2-aryl-Δ2-1,3,4-(oxa and thia)diazoline insecticidal and acaricidal agents | |
| US4791124A (en) | Photoactive azole pesticides | |
| US4699913A (en) | Substituted 4,5-dihydro-1,3,4-thiadiazoles useful as insecticides | |
| CA1310645C (en) | Insecticidal 6-aryl-pyridine thiosemicarbazones | |
| KR900000566B1 (ko) | 광활성 아졸 살충제 | |
| US4271166A (en) | N-(1,3,4-Thiadiazol-2-yl)benzamides | |
| JPS6033391B2 (ja) | 新規なフエニルカルバモイル‐２‐ピラゾリン、その製法およびそれを活性成分として含有する節足動物殺滅剤組成物 | |
| JP2553156B2 (ja) | アリールピロール殺昆虫、殺ダニおよび殺線虫剤およびそれらの調製方法 | |
| CA1110250A (en) | N-(1,3,4-thiadiazol-2-yl)benzamides | |
| EP1004241A1 (en) | 2-Aryl-Delta2-1,3,4- (oxa and thia)diazoline insecticidal and acaricidal agents | |
| US4812464A (en) | Pesticidal 2-pyridyl-4,5-dihydro-1,3,4-thiadiazoles | |
| KR810000057B1 (ko) | N-(1,3,4-티아디아졸-2-일) 벤즈아마이드 유도체의 제조방법 | |
| CS198218B2 (cs) | Zp&sob přípravy thiadiazolylbenzamidů | |
| JPS63166872A (ja) | 置換されたｎ−メチルイソキサゾリジン | |
| EP0002941B1 (en) | 2-substituted-n-(3-substituted phenyl)- oxazolidine-3-carbothioamides and their preparation, compositions and use | |
| US4897485A (en) | Insecticidal pyrid-3-yl-2,3-diaza-butadien-1-yl-disulfies | |
| CS207650B2 (cs) | Způsob výroby nových N-(l,3,4-thiadiazol-2-yl)benzamidů | |
| KR810000602B1 (ko) | N-(1, 3, 4-티아디아졸-2-일) 벤즈아미드의 제조방법 | |
| BE850712A (fr) | N-(1,3,4-thiadiazol-2-yl) benzamides insecticides |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| PCNP | Patent ceased through non-payment of renewal fee |