JPH0759556B2 - ピラゾール系化合物 - Google Patents
ピラゾール系化合物Info
- Publication number
- JPH0759556B2 JPH0759556B2 JP60025369A JP2536985A JPH0759556B2 JP H0759556 B2 JPH0759556 B2 JP H0759556B2 JP 60025369 A JP60025369 A JP 60025369A JP 2536985 A JP2536985 A JP 2536985A JP H0759556 B2 JPH0759556 B2 JP H0759556B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- carbon atoms
- methyl
- alkyl
- carboxamide
- 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 - Lifetime
Links
- -1 Pyrazole compound Chemical class 0.000 title claims description 690
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 597
- 125000004432 carbon atom Chemical group C* 0.000 claims description 437
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 claims description 282
- PPVUWDCETZMPLT-UHFFFAOYSA-N 1,3-dihydropyrazole-2-carboxamide Chemical compound NC(=O)N1CC=CN1 PPVUWDCETZMPLT-UHFFFAOYSA-N 0.000 claims description 249
- 125000004199 4-trifluoromethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C(F)(F)F 0.000 claims description 229
- 125000000217 alkyl group Chemical group 0.000 claims description 200
- 150000001875 compounds Chemical class 0.000 claims description 144
- 239000000203 mixture Substances 0.000 claims description 104
- 238000000034 method Methods 0.000 claims description 100
- 229910052739 hydrogen Inorganic materials 0.000 claims description 76
- 239000001257 hydrogen Substances 0.000 claims description 75
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical group C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 64
- 239000002904 solvent Substances 0.000 claims description 59
- 125000003107 substituted aryl group Chemical group 0.000 claims description 58
- 229910052757 nitrogen Inorganic materials 0.000 claims description 57
- 125000001424 substituent group Chemical group 0.000 claims description 57
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 51
- 150000002431 hydrogen Chemical group 0.000 claims description 49
- 229910052760 oxygen Inorganic materials 0.000 claims description 46
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 45
- 125000003118 aryl group Chemical group 0.000 claims description 38
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 38
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical group ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 36
- 238000006243 chemical reaction Methods 0.000 claims description 36
- 150000003839 salts Chemical class 0.000 claims description 36
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 35
- 229910052799 carbon Inorganic materials 0.000 claims description 33
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 32
- 239000002585 base Substances 0.000 claims description 31
- 229910052736 halogen Inorganic materials 0.000 claims description 30
- 150000002367 halogens Chemical group 0.000 claims description 28
- 239000003795 chemical substances by application Substances 0.000 claims description 25
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 claims description 24
- 229910052717 sulfur Inorganic materials 0.000 claims description 24
- 125000004863 4-trifluoromethoxyphenyl group Chemical group [H]C1=C([H])C(OC(F)(F)F)=C([H])C([H])=C1* 0.000 claims description 23
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 20
- 125000003545 alkoxy group Chemical group 0.000 claims description 20
- 125000003282 alkyl amino group Chemical group 0.000 claims description 20
- 125000003277 amino group Chemical group 0.000 claims description 20
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 20
- 125000004414 alkyl thio group Chemical group 0.000 claims description 19
- 230000007935 neutral effect Effects 0.000 claims description 19
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 19
- 125000004423 acyloxy group Chemical group 0.000 claims description 18
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 18
- 125000004691 alkyl thio carbonyl group Chemical group 0.000 claims description 17
- 239000012948 isocyanate Substances 0.000 claims description 17
- 241000238631 Hexapoda Species 0.000 claims description 16
- 229910052783 alkali metal Inorganic materials 0.000 claims description 16
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 16
- CYEBJEDOHLIWNP-UHFFFAOYSA-N methanethioamide Chemical group NC=S CYEBJEDOHLIWNP-UHFFFAOYSA-N 0.000 claims description 16
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 claims description 15
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 15
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 15
- 150000001408 amides Chemical class 0.000 claims description 13
- 238000004519 manufacturing process Methods 0.000 claims description 13
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 13
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 12
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 11
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 10
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims description 10
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 10
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 10
- 125000004422 alkyl sulphonamide group Chemical group 0.000 claims description 10
- 125000000304 alkynyl group Chemical group 0.000 claims description 10
- 125000003342 alkenyl group Chemical group 0.000 claims description 9
- 239000002168 alkylating agent Substances 0.000 claims description 9
- 229940100198 alkylating agent Drugs 0.000 claims description 9
- 150000001412 amines Chemical class 0.000 claims description 9
- 125000004429 atom Chemical group 0.000 claims description 9
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 9
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 claims description 9
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 9
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 8
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 8
- 229910052796 boron Inorganic materials 0.000 claims description 8
- GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 claims description 8
- ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical group [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 claims description 8
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 claims description 7
- 125000001246 bromo group Chemical group Br* 0.000 claims description 7
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 7
- 150000001983 dialkylethers Chemical group 0.000 claims description 7
- 125000001153 fluoro group Chemical group F* 0.000 claims description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
- 230000008569 process Effects 0.000 claims description 7
- DYGFZLXVZHSAOZ-UHFFFAOYSA-N methyl 5-(4-chlorophenyl)-2-[(4-chlorophenyl)carbamoyl]-4-methyl-3h-pyrazole-4-carboxylate Chemical compound COC(=O)C1(C)CN(C(=O)NC=2C=CC(Cl)=CC=2)N=C1C1=CC=C(Cl)C=C1 DYGFZLXVZHSAOZ-UHFFFAOYSA-N 0.000 claims description 6
- 238000011282 treatment Methods 0.000 claims description 6
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 5
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 5
- 229910000272 alkali metal oxide Inorganic materials 0.000 claims description 5
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 claims description 5
- 229910000287 alkaline earth metal oxide Inorganic materials 0.000 claims description 5
- 125000004647 alkyl sulfenyl group Chemical group 0.000 claims description 5
- 229910021529 ammonia Inorganic materials 0.000 claims description 5
- 239000001569 carbon dioxide Substances 0.000 claims description 5
- 229910002092 carbon dioxide Inorganic materials 0.000 claims description 5
- 230000000749 insecticidal effect Effects 0.000 claims description 5
- 150000003457 sulfones Chemical class 0.000 claims description 5
- 150000003462 sulfoxides Chemical class 0.000 claims description 5
- 150000003512 tertiary amines Chemical class 0.000 claims description 5
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 4
- FGCBXTLVUQGHQP-UHFFFAOYSA-N 3,4-dihydropyrazole-2-carboxamide Chemical compound NC(=O)N1CCC=N1 FGCBXTLVUQGHQP-UHFFFAOYSA-N 0.000 claims description 4
- 229910000102 alkali metal hydride Inorganic materials 0.000 claims description 4
- 150000008046 alkali metal hydrides Chemical class 0.000 claims description 4
- 150000001342 alkaline earth metals Chemical class 0.000 claims description 4
- 125000005910 alkyl carbonate group Chemical group 0.000 claims description 4
- 125000005392 carboxamide group Chemical group NC(=O)* 0.000 claims description 4
- 150000008280 chlorinated hydrocarbons Chemical group 0.000 claims description 4
- NEHMKBQYUWJMIP-NJFSPNSNSA-N chloro(114C)methane Chemical group [14CH3]Cl NEHMKBQYUWJMIP-NJFSPNSNSA-N 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 229940102396 methyl bromide Drugs 0.000 claims description 4
- JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 claims description 4
- 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 claims description 4
- BTJZURPKNVGPLL-UHFFFAOYSA-N 4-methyl-3,4-dihydropyrazole-2-carboxamide Chemical compound CC1C=NN(C1)C(=O)N BTJZURPKNVGPLL-UHFFFAOYSA-N 0.000 claims description 3
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 3
- 125000004404 heteroalkyl group Chemical group 0.000 claims description 3
- FQCDGZMHAIQKHL-UHFFFAOYSA-N methyl 4-methyl-5-[4-(trifluoromethyl)phenyl]-2-[[4-(trifluoromethyl)phenyl]carbamoyl]-3h-pyrazole-4-carboxylate Chemical compound COC(=O)C1(C)CN(C(=O)NC=2C=CC(=CC=2)C(F)(F)F)N=C1C1=CC=C(C(F)(F)F)C=C1 FQCDGZMHAIQKHL-UHFFFAOYSA-N 0.000 claims description 3
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 2
- 229910052720 vanadium Inorganic materials 0.000 claims 33
- 150000001721 carbon Chemical group 0.000 claims 23
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims 16
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 16
- 125000004442 acylamino group Chemical group 0.000 claims 13
- 125000005518 carboxamido group Chemical group 0.000 claims 13
- 125000000565 sulfonamide group Chemical group 0.000 claims 13
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 12
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 claims 11
- 102100037804 Inositol oxygenase Human genes 0.000 claims 10
- 101150089916 Miox gene Proteins 0.000 claims 10
- 101100440696 Caenorhabditis elegans cor-1 gene Proteins 0.000 claims 8
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 6
- 125000005422 alkyl sulfonamido group Chemical group 0.000 claims 6
- 125000005322 morpholin-1-yl group Chemical group 0.000 claims 6
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 5
- 125000005118 N-alkylcarbamoyl group Chemical group 0.000 claims 5
- 238000005917 acylation reaction Methods 0.000 claims 4
- JKJWYKGYGWOAHT-UHFFFAOYSA-N bis(prop-2-enyl) carbonate Chemical compound C=CCOC(=O)OCC=C JKJWYKGYGWOAHT-UHFFFAOYSA-N 0.000 claims 3
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 3
- 125000005420 sulfonamido group Chemical group S(=O)(=O)(N*)* 0.000 claims 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 2
- OSDWBNJEKMUWAV-UHFFFAOYSA-N Allyl chloride Chemical compound ClCC=C OSDWBNJEKMUWAV-UHFFFAOYSA-N 0.000 claims 2
- 230000029936 alkylation Effects 0.000 claims 2
- 238000005804 alkylation reaction Methods 0.000 claims 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 2
- YIHHMGYJFHGJAD-UHFFFAOYSA-N ethyl 5-(4-chlorophenyl)-2-[(4-chlorophenyl)carbamoyl]-4-methyl-3h-pyrazole-4-carboxylate Chemical compound CCOC(=O)C1(C)CN(C(=O)NC=2C=CC(Cl)=CC=2)N=C1C1=CC=C(Cl)C=C1 YIHHMGYJFHGJAD-UHFFFAOYSA-N 0.000 claims 2
- VKAKMNVDBDMONQ-UHFFFAOYSA-N methyl 2-[acetyl-(4-chlorophenyl)carbamoyl]-5-(4-chlorophenyl)-4-methyl-3h-pyrazole-4-carboxylate Chemical compound COC(=O)C1(C)CN(C(=O)N(C(C)=O)C=2C=CC(Cl)=CC=2)N=C1C1=CC=C(Cl)C=C1 VKAKMNVDBDMONQ-UHFFFAOYSA-N 0.000 claims 2
- GJAKVSRETQPSCE-UHFFFAOYSA-N methyl 5-(4-chlorophenyl)-2-[(4-chlorophenyl)-formylcarbamoyl]-4-methyl-3h-pyrazole-4-carboxylate Chemical compound COC(=O)C1(C)CN(C(=O)N(C=O)C=2C=CC(Cl)=CC=2)N=C1C1=CC=C(Cl)C=C1 GJAKVSRETQPSCE-UHFFFAOYSA-N 0.000 claims 2
- IWPDUXJRUXBXJA-UHFFFAOYSA-N methyl 5-(4-chlorophenyl)-2-[(4-chlorophenyl)-methoxycarbonylcarbamoyl]-4-methyl-3h-pyrazole-4-carboxylate Chemical compound C=1C=C(Cl)C=CC=1N(C(=O)OC)C(=O)N(N=1)CC(C)(C(=O)OC)C=1C1=CC=C(Cl)C=C1 IWPDUXJRUXBXJA-UHFFFAOYSA-N 0.000 claims 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N Formic acid Chemical group OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims 1
- 101100386054 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) CYS3 gene Proteins 0.000 claims 1
- 230000010933 acylation Effects 0.000 claims 1
- KTRFZWJCHOQHMN-UHFFFAOYSA-N chloromethanethioic s-acid Chemical compound SC(Cl)=O KTRFZWJCHOQHMN-UHFFFAOYSA-N 0.000 claims 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- 101150035983 str1 gene Proteins 0.000 claims 1
- 239000000243 solution Substances 0.000 description 67
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 61
- LDKSCZJUIURGMW-UHFFFAOYSA-N 1-isothiocyanato-3-methylsulfanylpropane Chemical group CSCCCN=C=S LDKSCZJUIURGMW-UHFFFAOYSA-N 0.000 description 58
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 50
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 48
- 238000002360 preparation method Methods 0.000 description 45
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 36
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 33
- 241000607479 Yersinia pestis Species 0.000 description 30
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 28
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 27
- 125000003368 amide group Chemical group 0.000 description 27
- 238000004566 IR spectroscopy Methods 0.000 description 19
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 18
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 17
- 239000007788 liquid Substances 0.000 description 16
- 238000003756 stirring Methods 0.000 description 16
- 239000013543 active substance Substances 0.000 description 15
- 230000000694 effects Effects 0.000 description 15
- 238000010992 reflux Methods 0.000 description 15
- 231100000614 poison Toxicity 0.000 description 14
- 239000007787 solid Substances 0.000 description 14
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 13
- 239000012044 organic layer Substances 0.000 description 13
- 125000003226 pyrazolyl group Chemical group 0.000 description 13
- 239000011541 reaction mixture Substances 0.000 description 13
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 238000009472 formulation Methods 0.000 description 12
- 239000000843 powder Substances 0.000 description 12
- DVLHGMFTRAFHPR-UHFFFAOYSA-N pyrazole-1-carboxamide Chemical compound NC(=O)N1C=CC=N1 DVLHGMFTRAFHPR-UHFFFAOYSA-N 0.000 description 12
- 235000011054 acetic acid Nutrition 0.000 description 11
- 238000002844 melting Methods 0.000 description 11
- 230000008018 melting Effects 0.000 description 11
- 239000002574 poison Substances 0.000 description 11
- 239000000126 substance Substances 0.000 description 11
- 241000196324 Embryophyta Species 0.000 description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 10
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- 239000002253 acid Substances 0.000 description 9
- 239000000969 carrier Substances 0.000 description 9
- 229940043279 diisopropylamine Drugs 0.000 description 9
- 239000000839 emulsion Substances 0.000 description 9
- 239000003921 oil Substances 0.000 description 9
- 235000019198 oils Nutrition 0.000 description 9
- 125000006275 3-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C([H])C(*)=C1[H] 0.000 description 8
- 239000003153 chemical reaction reagent Substances 0.000 description 8
- 239000012141 concentrate Substances 0.000 description 8
- 239000003995 emulsifying agent Substances 0.000 description 8
- 229910052751 metal Inorganic materials 0.000 description 8
- 239000002184 metal Substances 0.000 description 8
- 238000005507 spraying Methods 0.000 description 8
- 239000003981 vehicle Substances 0.000 description 8
- 150000003857 carboxamides Chemical class 0.000 description 7
- 235000008504 concentrate Nutrition 0.000 description 7
- 239000003085 diluting agent Substances 0.000 description 7
- 125000000524 functional group Chemical group 0.000 description 7
- 125000003944 tolyl group Chemical group 0.000 description 7
- 241000257159 Musca domestica Species 0.000 description 6
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 6
- 239000002270 dispersing agent Substances 0.000 description 6
- 238000003958 fumigation Methods 0.000 description 6
- 239000008187 granular material Substances 0.000 description 6
- 125000000623 heterocyclic group Chemical group 0.000 description 6
- 239000012312 sodium hydride Substances 0.000 description 6
- 229910000104 sodium hydride Inorganic materials 0.000 description 6
- 239000007921 spray Substances 0.000 description 6
- 125000004035 thiopropyl group Chemical group [H]SC([H])([H])C([H])([H])C([H])([H])* 0.000 description 6
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 description 5
- 241000462639 Epilachna varivestis Species 0.000 description 5
- 241001477931 Mythimna unipuncta Species 0.000 description 5
- 150000001298 alcohols Chemical class 0.000 description 5
- 150000003863 ammonium salts Chemical class 0.000 description 5
- 239000000460 chlorine Substances 0.000 description 5
- 235000015071 dressings Nutrition 0.000 description 5
- 125000005843 halogen group Chemical group 0.000 description 5
- 239000010410 layer Substances 0.000 description 5
- 125000004433 nitrogen atom Chemical group N* 0.000 description 5
- 229920000728 polyester Polymers 0.000 description 5
- 239000004094 surface-active agent Substances 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- 231100000331 toxic Toxicity 0.000 description 5
- 230000002588 toxic effect Effects 0.000 description 5
- HDLZNFDUULADBS-UHFFFAOYSA-N 3-(4-chlorophenyl)-4-methyl-4,5-dihydro-1h-pyrazole Chemical compound CC1CNN=C1C1=CC=C(Cl)C=C1 HDLZNFDUULADBS-UHFFFAOYSA-N 0.000 description 4
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 4
- 241000254175 Anthonomus grandis Species 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 241000254173 Coleoptera Species 0.000 description 4
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
- 241001521235 Spodoptera eridania Species 0.000 description 4
- 239000000853 adhesive Substances 0.000 description 4
- 230000001070 adhesive effect Effects 0.000 description 4
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 4
- 239000005667 attractant Substances 0.000 description 4
- 239000012267 brine Substances 0.000 description 4
- 239000012876 carrier material Substances 0.000 description 4
- 230000031902 chemoattractant activity Effects 0.000 description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- 239000004927 clay Substances 0.000 description 4
- 150000002170 ethers Chemical class 0.000 description 4
- 239000012530 fluid Substances 0.000 description 4
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine hydrate Chemical compound O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 4
- 229910052500 inorganic mineral Inorganic materials 0.000 description 4
- 150000002576 ketones Chemical class 0.000 description 4
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- DCYOBGZUOMKFPA-UHFFFAOYSA-N iron(2+);iron(3+);octadecacyanide Chemical compound [Fe+2].[Fe+2].[Fe+2].[Fe+3].[Fe+3].[Fe+3].[Fe+3].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-] DCYOBGZUOMKFPA-UHFFFAOYSA-N 0.000 description 1
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- LIOXBTXURYYQJE-UHFFFAOYSA-N methyl 2-[n-[5-(4-chlorophenyl)-4-methyl-4-(3-methylsulfanylpropyl)-3h-pyrazole-2-carbonyl]-4-(trifluoromethyl)anilino]-2-oxoacetate Chemical compound C=1C=C(C(F)(F)F)C=CC=1N(C(=O)C(=O)OC)C(=O)N(N=1)CC(C)(CCCSC)C=1C1=CC=C(Cl)C=C1 LIOXBTXURYYQJE-UHFFFAOYSA-N 0.000 description 1
- DHZKVTGKZJNKJK-UHFFFAOYSA-N methyl 2-[n-[5-[3-chloro-4-(trifluoromethyl)phenyl]-4-methyl-4-(3-methylsulfanylpropyl)-3h-pyrazole-2-carbonyl]-4-(trifluoromethyl)anilino]-2-oxoacetate Chemical compound C=1C=C(C(F)(F)F)C=CC=1N(C(=O)C(=O)OC)C(=O)N(N=1)CC(C)(CCCSC)C=1C1=CC=C(C(F)(F)F)C(Cl)=C1 DHZKVTGKZJNKJK-UHFFFAOYSA-N 0.000 description 1
- DPVOKXGLRHELGZ-UHFFFAOYSA-N methyl 2-carbamoyl-4-methyl-3,4-dihydropyrazole-5-carboxylate Chemical compound C(=O)(OC)C1=NN(CC1C)C(=O)N DPVOKXGLRHELGZ-UHFFFAOYSA-N 0.000 description 1
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- NELIAIPXAJJBKQ-UHFFFAOYSA-N n-iminoformamide Chemical compound N=NC=O NELIAIPXAJJBKQ-UHFFFAOYSA-N 0.000 description 1
- 229920005615 natural polymer Polymers 0.000 description 1
- 239000005645 nematicide Substances 0.000 description 1
- 150000002823 nitrates Chemical class 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- JCXJVPUVTGWSNB-UHFFFAOYSA-N nitrogen dioxide Inorganic materials O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- JPMIIZHYYWMHDT-UHFFFAOYSA-N octhilinone Chemical compound CCCCCCCCN1SC=CC1=O JPMIIZHYYWMHDT-UHFFFAOYSA-N 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000002903 organophosphorus compounds Chemical class 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- VIWWLVBTPJWYOP-UHFFFAOYSA-N oxolane;n-propan-2-ylpropan-2-amine Chemical compound C1CCOC1.CC(C)NC(C)C VIWWLVBTPJWYOP-UHFFFAOYSA-N 0.000 description 1
- 229920002866 paraformaldehyde Polymers 0.000 description 1
- 238000005192 partition Methods 0.000 description 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Inorganic materials [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 description 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 238000004525 petroleum distillation Methods 0.000 description 1
- DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 description 1
- 229940049953 phenylacetate Drugs 0.000 description 1
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- PTMHPRAIXMAOOB-UHFFFAOYSA-N phosphoramidic acid Chemical class NP(O)(O)=O PTMHPRAIXMAOOB-UHFFFAOYSA-N 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- 239000001007 phthalocyanine dye Substances 0.000 description 1
- 230000035479 physiological effects, processes and functions Effects 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920000136 polysorbate Polymers 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- VKJKEPKFPUWCAS-UHFFFAOYSA-M potassium chlorate Chemical compound [K+].[O-]Cl(=O)=O VKJKEPKFPUWCAS-UHFFFAOYSA-M 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 230000002062 proliferating effect Effects 0.000 description 1
- JKANAVGODYYCQF-UHFFFAOYSA-N prop-2-yn-1-amine Chemical compound NCC#C JKANAVGODYYCQF-UHFFFAOYSA-N 0.000 description 1
- YOROZPZOOUOFBU-UHFFFAOYSA-N propan-2-yl 3-[[5-[3-chloro-4-(trifluoromethyl)phenyl]-4-methyl-4-(3-methylsulfanylpropyl)-3h-pyrazole-2-carbonyl]amino]benzoate Chemical compound CSCCCC1(C)CN(C(=O)NC=2C=C(C=CC=2)C(=O)OC(C)C)N=C1C1=CC=C(C(F)(F)F)C(Cl)=C1 YOROZPZOOUOFBU-UHFFFAOYSA-N 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- IVNDPMMXZIBQJP-UHFFFAOYSA-N propyl 3-(4-chlorophenyl)-3-oxopropanoate Chemical compound CCCOC(=O)CC(=O)C1=CC=C(Cl)C=C1 IVNDPMMXZIBQJP-UHFFFAOYSA-N 0.000 description 1
- 239000011814 protection agent Substances 0.000 description 1
- 229960003351 prussian blue Drugs 0.000 description 1
- 239000013225 prussian blue Substances 0.000 description 1
- 150000003217 pyrazoles Chemical class 0.000 description 1
- 125000001725 pyrenyl group Chemical group 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 230000000979 retarding effect Effects 0.000 description 1
- 239000011435 rock Substances 0.000 description 1
- 239000003128 rodenticide Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910052624 sepiolite Inorganic materials 0.000 description 1
- 235000019355 sepiolite Nutrition 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 239000000779 smoke Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 229910052712 strontium Inorganic materials 0.000 description 1
- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 1
- 125000001174 sulfone group Chemical group 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 229920001059 synthetic polymer Polymers 0.000 description 1
- 239000002641 tar oil Substances 0.000 description 1
- FIALLSIWUOHQFY-UHFFFAOYSA-N tert-butyl 3-(4-chlorophenyl)-3-oxopropanoate Chemical compound CC(C)(C)OC(=O)CC(=O)C1=CC=C(Cl)C=C1 FIALLSIWUOHQFY-UHFFFAOYSA-N 0.000 description 1
- KTBFRHUFFWSAKJ-UHFFFAOYSA-N tert-butyl 3-[3-chloro-4-(trifluoromethoxy)phenyl]-3-oxopropanoate Chemical compound CC(C)(C)OC(=O)CC(=O)C1=CC=C(OC(F)(F)F)C(Cl)=C1 KTBFRHUFFWSAKJ-UHFFFAOYSA-N 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 125000004014 thioethyl group Chemical group [H]SC([H])([H])C([H])([H])* 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 231100000167 toxic agent Toxicity 0.000 description 1
- 239000003440 toxic substance Substances 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- GCRCSLNXFKCFHB-UHFFFAOYSA-N triethyl(hexyl)azanium Chemical compound CCCCCC[N+](CC)(CC)CC GCRCSLNXFKCFHB-UHFFFAOYSA-N 0.000 description 1
- JHNACYHGMDXEMK-UHFFFAOYSA-N triethyl(octyl)azanium Chemical compound CCCCCCCC[N+](CC)(CC)CC JHNACYHGMDXEMK-UHFFFAOYSA-N 0.000 description 1
- ZMANZCXQSJIPKH-UHFFFAOYSA-O triethylammonium ion Chemical compound CC[NH+](CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-O 0.000 description 1
- WSFDRHZUAHDHDN-UHFFFAOYSA-N trimethyl-[(4-methylphenyl)methyl]azanium Chemical compound CC1=CC=C(C[N+](C)(C)C)C=C1 WSFDRHZUAHDHDN-UHFFFAOYSA-N 0.000 description 1
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 1
- QDNCLIPKBNMUPP-UHFFFAOYSA-N trimethyloxidanium Chemical class C[O+](C)C QDNCLIPKBNMUPP-UHFFFAOYSA-N 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 238000009423 ventilation Methods 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 235000020234 walnut Nutrition 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 238000004078 waterproofing Methods 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- AMHNZOICSMBGDH-UHFFFAOYSA-L zineb Chemical compound [Zn+2].[S-]C(=S)NCCNC([S-])=S AMHNZOICSMBGDH-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/06—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
- A01N47/38—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the group >N—CO—N< where at least one nitrogen atom is part of a heterocyclic ring; Thio analogues thereof
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/40—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having a double or triple bond to nitrogen, e.g. cyanates, cyanamides
- A01N47/42—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having a double or triple bond to nitrogen, e.g. cyanates, cyanamides containing —N=CX2 groups, e.g. isothiourea
- A01N47/44—Guanidine; Derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/45—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation
- C07C45/46—Friedel-Crafts reactions
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
- C07C45/72—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups
- C07C45/75—Reactions with formaldehyde
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
- C07C49/80—Ketones containing a keto group bound to a six-membered aromatic ring containing halogen
- C07C49/813—Ketones containing a keto group bound to a six-membered aromatic ring containing halogen polycyclic
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/06—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D231/08—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with oxygen or sulfur atoms directly attached to ring carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Plant Pathology (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Engineering & Computer Science (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US580963 | 1984-02-15 | ||
| US58096384A | 1984-02-16 | 1984-02-16 | |
| US689671 | 1985-01-11 | ||
| US06/689,671 US4663341A (en) | 1984-02-16 | 1985-01-11 | Insecticidal n-aryl-3-aryl-4,5-dihydro-1h-pyrazole-1-carboxamides |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS60190765A JPS60190765A (ja) | 1985-09-28 |
| JPH0759556B2 true JPH0759556B2 (ja) | 1995-06-28 |
Family
ID=27078174
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP60025369A Expired - Lifetime JPH0759556B2 (ja) | 1984-02-16 | 1985-02-14 | ピラゾール系化合物 |
Country Status (22)
| Country | Link |
|---|---|
| US (1) | US4663341A (enExample) |
| EP (1) | EP0153127B1 (enExample) |
| JP (1) | JPH0759556B2 (enExample) |
| KR (1) | KR880001987B1 (enExample) |
| AR (1) | AR243871A1 (enExample) |
| AU (1) | AU588796B2 (enExample) |
| BR (1) | BR8500673A (enExample) |
| CA (1) | CA1275289C (enExample) |
| DE (1) | DE3582341D1 (enExample) |
| DK (1) | DK68285A (enExample) |
| EG (1) | EG17990A (enExample) |
| ES (1) | ES8607246A1 (enExample) |
| FI (1) | FI90975C (enExample) |
| GR (1) | GR850393B (enExample) |
| HU (1) | HU206248B (enExample) |
| IE (1) | IE57861B1 (enExample) |
| IL (1) | IL74305A (enExample) |
| NO (1) | NO171364C (enExample) |
| NZ (1) | NZ211097A (enExample) |
| PH (1) | PH22521A (enExample) |
| PT (1) | PT79978B (enExample) |
| SG (1) | SG53591G (enExample) |
Families Citing this family (43)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU570298B2 (en) * | 1984-02-21 | 1988-03-10 | E.I. Du Pont De Nemours And Company | Aryl or heterocyclic sulfonyl urea derivatives with herbicidal properties |
| EP0182746A3 (de) * | 1984-11-16 | 1988-10-12 | Ciba-Geigy Ag | Pyrazolinderivate |
| US4767779A (en) * | 1985-09-24 | 1988-08-30 | Fmc Corporation | Pyrazoline-1-carboxamides, composition containing them, and insecticidal method of using them |
| DE3545786A1 (de) * | 1985-12-21 | 1987-06-25 | Schering Ag | Pyrazolinderivate, ihre herstellung und ihre verwendung als mittel mit insektizider wirkung |
| EP0268892A3 (en) * | 1986-11-06 | 1990-10-10 | Nissan Chemical Industries Ltd. | Substituted-amido derivatives, method for preparation of the same and phytopathogenic fungicides containing the same |
| DE3638631A1 (de) * | 1986-11-11 | 1988-05-26 | Schering Ag | Pyrazoline, ihre herstellung und ihre verwendung als mittel mit insektizider und akarizider wirkung |
| US4822613A (en) * | 1986-12-15 | 1989-04-18 | S. C. Johnson & Son, Inc. | Water-soluble foamable insecticidally-active compositions |
| US5091405A (en) * | 1987-01-05 | 1992-02-25 | E. I. Du Pont De Nemours And Company | Insecticidal pyrazolines |
| US4983389A (en) * | 1987-04-01 | 1991-01-08 | Lee County Mosquito Control District | Herbicidal delivery compositions and methods for controlling plant populations in aquatic and wetland environments |
| US4985251A (en) * | 1987-04-01 | 1991-01-15 | Lee County Mosquito Control District | Flowable insecticidal delivery compositions and methods for controlling insect populations in an aquatic environment |
| US4983390A (en) * | 1987-04-01 | 1991-01-08 | Lee County Mosquito Control District | Terrestrial delivery compositions and methods for controlling insect and habitat-associated pest populations in terrestrial environments |
| US4960784A (en) * | 1987-04-09 | 1990-10-02 | E. I. Du Pont De Nemours And Company | Insecticidal substituted indazoles |
| EP0362216A1 (en) * | 1987-04-09 | 1990-04-11 | E.I. Du Pont De Nemours And Company | Insecticidal substituted indazoles |
| US4990514A (en) * | 1987-04-27 | 1991-02-05 | The Clorox Company | Non-particulate, non-flowable, non-repellant insecticide-bait composition for the control of cockroaches |
| US5006524A (en) * | 1987-07-17 | 1991-04-09 | E. I. Du Pont De Nemours And Company | Triphenyl pyrazoline compounds which are useful as insecticides |
| EP0367796A1 (en) * | 1987-07-17 | 1990-05-16 | E.I. Du Pont De Nemours And Company | Insecticidal pyrazolines |
| EP0300692A1 (en) * | 1987-07-17 | 1989-01-25 | E.I. Du Pont De Nemours And Company | Insecticidal pyrazolines |
| US5116850A (en) * | 1987-11-30 | 1992-05-26 | E. I. Du Pont De Nemours And Co. | Heterocyclic pyrazoline carboxanilides |
| JPH04501108A (ja) * | 1988-09-22 | 1992-02-27 | イー・アイ・デユポン・ドウ・ヌムール・アンド・カンパニー | 置換インダゾール殺節足動物剤 |
| US5591764A (en) * | 1988-09-27 | 1997-01-07 | E. I. Du Pont De Nemours And Company | N-acylated pyrazolines |
| JPH04500810A (ja) * | 1988-09-27 | 1992-02-13 | イー・アイ・デユポン・ドウ・ヌムール・アンド・カンパニー | Ｎ―スルフエニル化、及びｎ―アシル化ピラゾリン |
| US5491162A (en) * | 1988-09-27 | 1996-02-13 | E. I. Du Pont De Nemours And Company | N-acylated pyrazolines, compositions and use |
| AU4400389A (en) * | 1988-10-11 | 1990-05-01 | E.I. Du Pont De Nemours And Company | Substituted indazoles as arthropodicides |
| CA2074179A1 (en) * | 1990-01-31 | 1991-08-01 | Charles R. Harrison | Arthropodicidal pyrazolines, pyrazolidines and hyrazines |
| AU7884691A (en) * | 1990-05-15 | 1991-12-10 | E.I. Du Pont De Nemours And Company | Arthropodicidal tetrahydropyridazines |
| DE69131899T2 (de) * | 1990-07-13 | 2000-08-17 | Rohm And Haas Co., Philadelphia | N-Aryl-3-aryl-4-substituierte-4,5-dihydro-1H-pyrazol-1-carboxamide und Verfahren zu deren Herstellung |
| US5798311A (en) * | 1990-07-13 | 1998-08-25 | Rohm And Haas Company | N-aryl-3-aryl-4-substituted-4,5-dihydro-1H-pyrazole-1-carboxamides and methods of their production |
| CA2056018A1 (en) * | 1990-12-10 | 1992-06-11 | Richard Martin Jacobson | N-aryl-3-aryl-4-substituted-2,3,4,5-tetrahydro-1h-pyrazole- 1-carboxamides and methods for their production |
| WO1993005024A1 (en) * | 1991-08-28 | 1993-03-18 | E.I. Du Pont De Nemours And Company | Arthropodicidal anilides |
| US5525622A (en) * | 1991-08-28 | 1996-06-11 | Bayer Aktiengesellschaft | Substituted pyrazolines |
| WO1995016676A1 (en) * | 1993-12-17 | 1995-06-22 | E.I. Du Pont De Nemours And Company | Arthropodicidal pentafluorothio substituted anilides |
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| MY138097A (en) * | 2000-03-22 | 2009-04-30 | Du Pont | Insecticidal anthranilamides |
| HUP0301189A3 (en) * | 2000-07-24 | 2003-11-28 | Bayer Cropscience Ag | Pyrazolyl biphenyl carboxamides, intermediates, preparation and use thereof for controlling undesired microorganisms |
| US7459562B2 (en) * | 2004-04-23 | 2008-12-02 | Bristol-Myers Squibb Company | Monocyclic heterocycles as kinase inhibitors |
| TW200538453A (en) * | 2004-04-26 | 2005-12-01 | Bristol Myers Squibb Co | Bicyclic heterocycles as kinase inhibitors |
| US7439246B2 (en) * | 2004-06-28 | 2008-10-21 | Bristol-Myers Squibb Company | Fused heterocyclic kinase inhibitors |
| US20050288290A1 (en) | 2004-06-28 | 2005-12-29 | Borzilleri Robert M | Fused heterocyclic kinase inhibitors |
| US7432373B2 (en) * | 2004-06-28 | 2008-10-07 | Bristol-Meyers Squibb Company | Processes and intermediates useful for preparing fused heterocyclic kinase inhibitors |
| JP5164510B2 (ja) * | 2006-10-06 | 2013-03-21 | 日本曹達株式会社 | 含窒素複素環化合物および有害生物防除剤 |
| JP5164525B2 (ja) * | 2006-11-01 | 2013-03-21 | 日本曹達株式会社 | 含窒素へテロ環化合物および有害生物防除剤 |
| GB0823000D0 (en) * | 2008-12-17 | 2009-01-28 | Syngenta Participations Ag | Isothiazole and pyrazole derivatives with plant growth regulating properties |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4010271A (en) * | 1972-02-09 | 1977-03-01 | U.S. Philips Corporation | Novel pyrazoline compounds having insecticidal activity |
| BE795264A (fr) | 1972-02-09 | 1973-08-09 | Philips Nv | Nouveaux composes de pyrazoline a activite insecticide |
| US3991073A (en) * | 1972-02-09 | 1976-11-09 | U.S. Philips Corporation | Pyrazoline compounds having insecticidal activity |
| US4095026A (en) * | 1972-02-09 | 1978-06-13 | U.S. Philips Corporation | Pyrazoline compounds having insecticidal activity |
| NL158178B (nl) * | 1974-07-12 | 1978-10-16 | Philips Nv | Werkwijze ter bereiding van insekticide preparaten die een pyrazolinederivaat bevatten, aldus verkregen gevormde preparaten, en werkwijze ter bereiding van pyrazolinederivaten met insekticide werking. |
| US4156007A (en) * | 1974-07-12 | 1979-05-22 | U.S. Philips Corporation | Pyrazoline compounds |
| US4174393A (en) * | 1975-07-09 | 1979-11-13 | Duphar International Research B.V. | 1,3,4-Substituted pyrazoline derivatives |
| DE2700288A1 (de) * | 1977-01-05 | 1978-07-13 | Bayer Ag | Phenylcarbamoyl-pyrazoline, verfahren zu ihrer herstellung und ihre verwendung als insektizide |
| DE2700289A1 (de) * | 1977-01-05 | 1978-07-06 | Bayer Ag | Substituierte phenylcarbamoyl-2- pyrazoline, verfahren zu ihrer herstellung und ihre verwendung als insektizide |
| EP0004733A3 (en) * | 1978-03-31 | 1979-10-31 | Imperial Chemical Industries Plc | Diaryl substituted pyrazoline carboxanilides, processes for preparing them, insecticidal compositions and uses thereof, and intermediates therefor |
| DE3064749D1 (en) * | 1979-07-03 | 1983-10-13 | Duphar Int Res | New pyrazoline derivatives, method of preparing the new compounds, as well as insecticidal composition on the basis of these new compounds |
| IN157732B (enExample) * | 1981-02-06 | 1986-05-24 | Svenska Rotor Maskiner Ab | |
| US4464386A (en) * | 1981-02-17 | 1984-08-07 | Nissan Chemical Industries, Ltd. | Insecticidal 3-difluoromethoxyphenyl-1-phenylcarbamoyl-2-pyrazolines |
| GB2093836B (en) * | 1981-02-17 | 1984-09-05 | Nissan Chemical Ind Ltd | Insecticidal pyrazoline derivatives |
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| DE3264760D1 (en) * | 1981-05-12 | 1985-08-22 | Duphar Int Res | New pyrazoline derivatives, method of preparing the new compounds, as well as insecticidal compositions on the basis of these compounds |
| JPS58128374A (ja) * | 1982-01-26 | 1983-07-30 | Nissan Chem Ind Ltd | 新規ピラゾリン誘導体，その製造方法およびそれを有効成分として含有する有害生物防除剤 |
| DE3376212D1 (de) * | 1982-12-30 | 1988-05-11 | Schering Agrochemicals Ltd | Pyrazoline insecticides |
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-
1985
- 1985-01-11 US US06/689,671 patent/US4663341A/en not_active Expired - Lifetime
- 1985-01-31 PH PH31796A patent/PH22521A/en unknown
- 1985-02-01 CA CA000473376A patent/CA1275289C/en not_active Expired - Fee Related
- 1985-02-06 AR AR85299440A patent/AR243871A1/es active
- 1985-02-10 EG EG81/85A patent/EG17990A/xx active
- 1985-02-11 IL IL74305A patent/IL74305A/xx unknown
- 1985-02-12 NZ NZ211097A patent/NZ211097A/xx unknown
- 1985-02-12 EP EP85300908A patent/EP0153127B1/en not_active Expired - Lifetime
- 1985-02-12 DE DE8585300908T patent/DE3582341D1/de not_active Expired - Fee Related
- 1985-02-13 AU AU38674/85A patent/AU588796B2/en not_active Ceased
- 1985-02-13 NO NO850545A patent/NO171364C/no unknown
- 1985-02-13 BR BR8500673A patent/BR8500673A/pt not_active IP Right Cessation
- 1985-02-13 ES ES540366A patent/ES8607246A1/es not_active Expired
- 1985-02-14 DK DK68285A patent/DK68285A/da not_active Application Discontinuation
- 1985-02-14 GR GR850393A patent/GR850393B/el unknown
- 1985-02-14 JP JP60025369A patent/JPH0759556B2/ja not_active Expired - Lifetime
- 1985-02-14 IE IE364/85A patent/IE57861B1/en not_active IP Right Cessation
- 1985-02-14 HU HU85553A patent/HU206248B/hu not_active IP Right Cessation
- 1985-02-14 FI FI850620A patent/FI90975C/fi not_active IP Right Cessation
- 1985-02-15 PT PT79978A patent/PT79978B/pt not_active IP Right Cessation
- 1985-02-15 KR KR1019850000938A patent/KR880001987B1/ko not_active Expired
-
1991
- 1991-07-09 SG SG535/91A patent/SG53591G/en unknown
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