JP2010502663A - 殺虫化合物 - Google Patents
殺虫化合物 Download PDFInfo
- Publication number
- JP2010502663A JP2010502663A JP2009527061A JP2009527061A JP2010502663A JP 2010502663 A JP2010502663 A JP 2010502663A JP 2009527061 A JP2009527061 A JP 2009527061A JP 2009527061 A JP2009527061 A JP 2009527061A JP 2010502663 A JP2010502663 A JP 2010502663A
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- JP
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- Prior art keywords
- phenyl
- formula
- methyl
- compound
- fluoro
- 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.)
- Granted
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 209
- 230000000749 insecticidal effect Effects 0.000 title claims abstract description 13
- 239000000203 mixture Substances 0.000 claims abstract description 90
- 241000607479 Yersinia pestis Species 0.000 claims abstract description 24
- 238000000034 method Methods 0.000 claims abstract description 23
- 230000000895 acaricidal effect Effects 0.000 claims abstract description 14
- 241000244206 Nematoda Species 0.000 claims abstract description 11
- 230000001069 nematicidal effect Effects 0.000 claims abstract description 10
- 150000003839 salts Chemical class 0.000 claims abstract description 9
- 230000002013 molluscicidal effect Effects 0.000 claims abstract description 8
- 241000238876 Acari Species 0.000 claims abstract description 7
- 241000238631 Hexapoda Species 0.000 claims abstract description 7
- 241000237852 Mollusca Species 0.000 claims abstract description 6
- 150000001204 N-oxides Chemical class 0.000 claims abstract description 5
- 241001465754 Metazoa Species 0.000 claims abstract 2
- -1 nitro, hydroxy Chemical group 0.000 claims description 363
- 125000001424 substituent group Chemical group 0.000 claims description 52
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 39
- 239000001257 hydrogen Substances 0.000 claims description 35
- 229910052739 hydrogen Inorganic materials 0.000 claims description 35
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 33
- 229910052736 halogen Inorganic materials 0.000 claims description 27
- 150000002367 halogens Chemical class 0.000 claims description 27
- 239000000460 chlorine Chemical group 0.000 claims description 26
- 229910052760 oxygen Inorganic materials 0.000 claims description 26
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 25
- 229910052794 bromium Inorganic materials 0.000 claims description 25
- 229910052801 chlorine Inorganic materials 0.000 claims description 25
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 25
- 239000001301 oxygen Substances 0.000 claims description 25
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 21
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 19
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 19
- 229910052731 fluorine Inorganic materials 0.000 claims description 19
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 18
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 15
- 125000003118 aryl group Chemical group 0.000 claims description 14
- 125000004076 pyridyl group Chemical group 0.000 claims description 13
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 11
- 239000011737 fluorine Chemical group 0.000 claims description 11
- 125000002541 furyl group Chemical group 0.000 claims description 11
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 11
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 11
- 125000001544 thienyl group Chemical group 0.000 claims description 11
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 10
- 239000011593 sulfur Substances 0.000 claims description 10
- 229910052717 sulfur Inorganic materials 0.000 claims description 10
- 125000004455 (C1-C3) alkylthio group Chemical group 0.000 claims description 9
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 9
- 125000000623 heterocyclic group Chemical group 0.000 claims description 8
- 229910052757 nitrogen Inorganic materials 0.000 claims description 8
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 8
- 125000002883 imidazolyl group Chemical group 0.000 claims description 7
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 7
- 125000002971 oxazolyl group Chemical group 0.000 claims description 7
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 7
- 125000001113 thiadiazolyl group Chemical group 0.000 claims description 7
- 125000000335 thiazolyl group Chemical group 0.000 claims description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 5
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims description 4
- 125000006677 (C1-C3) haloalkoxy group Chemical group 0.000 claims description 3
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 3
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims description 3
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims description 3
- 125000003830 C1- C4 alkylcarbonylamino group Chemical group 0.000 claims description 2
- 125000001153 fluoro group Chemical group F* 0.000 claims description 2
- 230000002401 inhibitory effect Effects 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 230000000361 pesticidal effect Effects 0.000 claims description 2
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- 238000002360 preparation method Methods 0.000 abstract description 28
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 63
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 27
- 239000000243 solution Substances 0.000 description 23
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 18
- 239000011541 reaction mixture Substances 0.000 description 18
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 17
- 239000007788 liquid Substances 0.000 description 17
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 16
- 238000005160 1H NMR spectroscopy Methods 0.000 description 15
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 150000002431 hydrogen Chemical class 0.000 description 15
- 238000009472 formulation Methods 0.000 description 14
- 239000002904 solvent Substances 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 13
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 11
- 239000004480 active ingredient Substances 0.000 description 11
- 239000012074 organic phase Substances 0.000 description 11
- 239000012071 phase Substances 0.000 description 11
- UHEJHCJGXRXRMF-UHFFFAOYSA-N 4-(1,1,1,2,3,3,3-heptafluoropropan-2-yl)-2,6-dimethylbenzoyl chloride Chemical compound CC1=CC(C(F)(C(F)(F)F)C(F)(F)F)=CC(C)=C1C(Cl)=O UHEJHCJGXRXRMF-UHFFFAOYSA-N 0.000 description 10
- 241000196324 Embryophyta Species 0.000 description 10
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 10
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
- 239000002917 insecticide Substances 0.000 description 10
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 9
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 9
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 239000002253 acid Substances 0.000 description 9
- 239000008187 granular material Substances 0.000 description 9
- 229910052938 sodium sulfate Inorganic materials 0.000 description 9
- 235000011152 sodium sulphate Nutrition 0.000 description 9
- 239000004546 suspension concentrate Substances 0.000 description 9
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 description 8
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 8
- 150000001412 amines Chemical class 0.000 description 8
- 239000003795 chemical substances by application Substances 0.000 description 8
- QPJDMGCKMHUXFD-UHFFFAOYSA-N cyanogen chloride Chemical compound ClC#N QPJDMGCKMHUXFD-UHFFFAOYSA-N 0.000 description 8
- 150000004820 halides Chemical class 0.000 description 8
- 125000001072 heteroaryl group Chemical group 0.000 description 8
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 8
- 229920006395 saturated elastomer Polymers 0.000 description 8
- 235000017557 sodium bicarbonate Nutrition 0.000 description 8
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 8
- 239000007787 solid Substances 0.000 description 8
- 239000011550 stock solution Substances 0.000 description 8
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 description 7
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 description 7
- 125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 description 7
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 7
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 7
- 125000004199 4-trifluoromethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C(F)(F)F 0.000 description 7
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 7
- 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 7
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 7
- 238000010828 elution Methods 0.000 description 7
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- 150000002148 esters Chemical class 0.000 description 7
- 230000012010 growth Effects 0.000 description 7
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 7
- 239000000843 powder Substances 0.000 description 7
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 6
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 6
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- 239000008346 aqueous phase Substances 0.000 description 6
- 239000000839 emulsion Substances 0.000 description 6
- VHFBTKQOIBRGQP-UHFFFAOYSA-N fluoro nitrate Chemical compound [O-][N+](=O)OF VHFBTKQOIBRGQP-UHFFFAOYSA-N 0.000 description 6
- 239000000543 intermediate Substances 0.000 description 6
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 6
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- 125000004512 1,2,3-thiadiazol-4-yl group Chemical group S1N=NC(=C1)* 0.000 description 5
- 125000006276 2-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C(*)C([H])=C1[H] 0.000 description 5
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 5
- 241000256118 Aedes aegypti Species 0.000 description 5
- 241000256602 Isoptera Species 0.000 description 5
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- 125000003342 alkenyl group Chemical group 0.000 description 5
- 125000000217 alkyl group Chemical group 0.000 description 5
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- QFFYLJYLEUZXHZ-UHFFFAOYSA-N methyl 2,6-diethyl-4-(1,1,1,2,3,3,3-heptafluoropropan-2-yl)benzoate Chemical compound CCC1=CC(C(F)(C(F)(F)F)C(F)(F)F)=CC(CC)=C1C(=O)OC QFFYLJYLEUZXHZ-UHFFFAOYSA-N 0.000 description 5
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- 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 4
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- 0 CC(N*)=*C(N(*)C(*)=*)=* Chemical compound CC(N*)=*C(N(*)C(*)=*)=* 0.000 description 4
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- WRDOHPZNJOBCHG-UHFFFAOYSA-N 4-(1,1,1,2,3,3,3-heptafluoropropan-2-yl)-2,6-dimethylbenzoic acid Chemical compound CC1=CC(C(F)(C(F)(F)F)C(F)(F)F)=CC(C)=C1C(O)=O WRDOHPZNJOBCHG-UHFFFAOYSA-N 0.000 description 3
- CZKLEJHVLCMVQR-UHFFFAOYSA-N 4-fluorobenzoyl chloride Chemical compound FC1=CC=C(C(Cl)=O)C=C1 CZKLEJHVLCMVQR-UHFFFAOYSA-N 0.000 description 3
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- NYPJDWWKZLNGGM-UHFFFAOYSA-N fenvalerate Chemical compound C=1C=C(Cl)C=CC=1C(C(C)C)C(=O)OC(C#N)C(C=1)=CC=CC=1OC1=CC=CC=C1 NYPJDWWKZLNGGM-UHFFFAOYSA-N 0.000 description 3
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- 125000005843 halogen group Chemical group 0.000 description 3
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- LFQUOIBUUUYGBW-UHFFFAOYSA-N n-(2-cyano-5-nitrophenyl)-4-fluorobenzamide Chemical compound [O-][N+](=O)C1=CC=C(C#N)C(NC(=O)C=2C=CC(F)=CC=2)=C1 LFQUOIBUUUYGBW-UHFFFAOYSA-N 0.000 description 3
- DPBQLKDBFAVZMQ-UHFFFAOYSA-N n-(3-aminophenyl)-4-(1,1,1,2,3,3,3-heptafluoropropan-2-yl)-2,6-dimethylbenzamide Chemical compound CC1=CC(C(F)(C(F)(F)F)C(F)(F)F)=CC(C)=C1C(=O)NC1=CC=CC(N)=C1 DPBQLKDBFAVZMQ-UHFFFAOYSA-N 0.000 description 3
- SNVVXNXXINEKAT-UHFFFAOYSA-N n-(5-amino-2-cyanophenyl)-4-fluorobenzamide Chemical compound NC1=CC=C(C#N)C(NC(=O)C=2C=CC(F)=CC=2)=C1 SNVVXNXXINEKAT-UHFFFAOYSA-N 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 150000002825 nitriles Chemical class 0.000 description 3
- 235000019198 oils Nutrition 0.000 description 3
- 229910052763 palladium Inorganic materials 0.000 description 3
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- ZZYSLNWGKKDOML-UHFFFAOYSA-N tebufenpyrad Chemical compound CCC1=NN(C)C(C(=O)NCC=2C=CC(=CC=2)C(C)(C)C)=C1Cl ZZYSLNWGKKDOML-UHFFFAOYSA-N 0.000 description 1
- ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
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- ILJSQTXMGCGYMG-UHFFFAOYSA-N triacetic acid Chemical compound CC(=O)CC(=O)CC(O)=O ILJSQTXMGCGYMG-UHFFFAOYSA-N 0.000 description 1
- BAZVSMNPJJMILC-UHFFFAOYSA-N triadimenol Chemical compound C1=NC=NN1C(C(O)C(C)(C)C)OC1=CC=C(Cl)C=C1 BAZVSMNPJJMILC-UHFFFAOYSA-N 0.000 description 1
- 125000004665 trialkylsilyl group Chemical group 0.000 description 1
- NKNFWVNSBIXGLL-UHFFFAOYSA-N triazamate Chemical compound CCOC(=O)CSC1=NC(C(C)(C)C)=NN1C(=O)N(C)C NKNFWVNSBIXGLL-UHFFFAOYSA-N 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- AMFGTOFWMRQMEM-UHFFFAOYSA-N triazophos Chemical compound N1=C(OP(=S)(OCC)OCC)N=CN1C1=CC=CC=C1 AMFGTOFWMRQMEM-UHFFFAOYSA-N 0.000 description 1
- IQGKIPDJXCAMSM-UHFFFAOYSA-N triazoxide Chemical compound N=1C2=CC=C(Cl)C=C2[N+]([O-])=NC=1N1C=CN=C1 IQGKIPDJXCAMSM-UHFFFAOYSA-N 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- DQJCHOQLCLEDLL-UHFFFAOYSA-N tricyclazole Chemical compound CC1=CC=CC2=C1N1C=NN=C1S2 DQJCHOQLCLEDLL-UHFFFAOYSA-N 0.000 description 1
- ONCZDRURRATYFI-TVJDWZFNSA-N trifloxystrobin Chemical compound CO\N=C(\C(=O)OC)C1=CC=CC=C1CO\N=C(/C)C1=CC=CC(C(F)(F)F)=C1 ONCZDRURRATYFI-TVJDWZFNSA-N 0.000 description 1
- HSMVPDGQOIQYSR-KGENOOAVSA-N triflumizole Chemical compound C1=CN=CN1C(/COCCC)=N/C1=CC=C(Cl)C=C1C(F)(F)F HSMVPDGQOIQYSR-KGENOOAVSA-N 0.000 description 1
- XAIPTRIXGHTTNT-UHFFFAOYSA-N triflumuron Chemical compound C1=CC(OC(F)(F)F)=CC=C1NC(=O)NC(=O)C1=CC=CC=C1Cl XAIPTRIXGHTTNT-UHFFFAOYSA-N 0.000 description 1
- 125000004360 trifluorophenyl group Chemical group 0.000 description 1
- JARYYMUOCXVXNK-CSLFJTBJSA-N validamycin A Chemical compound N([C@H]1C[C@@H]([C@H]([C@H](O)[C@H]1O)O[C@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)O)CO)[C@H]1C=C(CO)[C@@H](O)[C@H](O)[C@H]1O JARYYMUOCXVXNK-CSLFJTBJSA-N 0.000 description 1
- 239000000052 vinegar Substances 0.000 description 1
- 235000021419 vinegar Nutrition 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
- 239000004564 water dispersible powder for slurry treatment Substances 0.000 description 1
- 239000004549 water soluble granule Substances 0.000 description 1
- 239000003021 water soluble solvent Substances 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- DUBNHZYBDBBJHD-UHFFFAOYSA-L ziram Chemical compound [Zn+2].CN(C)C([S-])=S.CN(C)C([S-])=S DUBNHZYBDBBJHD-UHFFFAOYSA-L 0.000 description 1
- FJBGIXKIXPUXBY-UHFFFAOYSA-N {2-[3-(4-chlorophenyl)propyl]-2,4,4-trimethyl-1,3-oxazolidin-3-yl}(imidazol-1-yl)methanone Chemical compound C1=CN=CN1C(=O)N1C(C)(C)COC1(C)CCCC1=CC=C(Cl)C=C1 FJBGIXKIXPUXBY-UHFFFAOYSA-N 0.000 description 1
- JLYXXMFPNIAWKQ-UHFFFAOYSA-N γ Benzene hexachloride Chemical compound ClC1C(Cl)C(Cl)C(Cl)C(Cl)C1Cl JLYXXMFPNIAWKQ-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/64—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings
- C07C233/77—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups
- C07C233/80—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
- C07C235/42—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton
- C07C235/44—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton with carbon atoms of carboxamide groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring
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Abstract
Description
式(I)の化合物、
Xは各々独立に水素、ハロゲン、シアノ、C1−C4アルキル、C1−C4ハロアルキル又はC1−C4アルコキシであり;
R1及びR2は、互いに独立に水素、C1−C4アルキル又はC1−C4アルキルカルボニルであり;
G1及びG2は、互いに独立に酸素又は硫黄であり;
Q1は、アリールもしくは1〜5の置換基R3で置換されたアリールであり、R3は同種でも異種でもよく、又は、Q1はヘテロシクリルもしくは1〜5の置換基R3で置換されたヘテロシクリルであり、R3は同種でも異種でもよく、ここで、
R3は各々独立にシアノ、ニトロ、ヒドロキシ、ハロゲン、C1−C4アルキル、C1−C4ハロアルキル、C2−C4アルケニル、C2−C4ハロアルケニル、C2−C4アルキニル、C2−C4ハロアルキニル、C3−C6シクロアルキル、C3−C6ハロシクロアルキル、C1−C3アルコキシ、C1−C3ハロアルコキシ、C1−C3アルキルチオ、C1−C3ハロアルキルチオ、C1−C3アルキルスルフィニル、C1−C3ハロアルキルスルフィニル、C1−C3アルキルスルホニル、C1−C3ハロアルキルスルホニル、アミノ、C1−C4アルキルアミノ、ジ−(C1−C4アルキル)アミノ、C1−C4アルキルカルボニル、C1−C4アルキルカルボニルオキシ、C1−C4アルコキシカルボニル、C1−C4アルキルカルボニルアミノ、又は、ハロゲン、C1−C4アルキル、C1−C4ハロアルキル、C1−C4アルコキシもしくはC1−C4ハロアルコキシから独立に選択される1〜3の置換基によって置換されていてもよいアリール、又は、ハロゲン、C1−C4アルキル、C1−C4ハロアルキル、C1−C4アルコキシもしくはC1−C4ハロアルコキシから独立に選択される1〜3の置換基によって置換されていてもよいヘテロアリールであり;
Q2は、式(II)又は(III)部分、
Y1及びY5は、各々独立に、水素、シアノ、ハロゲン、C1−C4アルキル、C1−C4ハロアルキル、C1−C4アルコキシ−C1−C4−アルキル、C1−C3アルキルチオ、C1−C3ハロアルキルチオ、C1−C3アルキルスルフィニル、C1−C3ハロアルキルスルフィニル、C1−C3アルキルスルホニル又はC1−C3ハロアルキルスルホニルであり;
Y3は、C2−C6ペルフルオロアルキル、C1−C6ペルフルオロアルキルチオ、C1−C6ペルフルオロアルキルスルフィニル又はC1−C6ペルフルオロアルキルスルホニルであり;
Y2及びY4は、各々独立に、水素、ハロゲン又はC1−C4アルキルであり;
Y6及びY9は、各々独立に、水素、シアノ、ハロゲン、C1−C4アルキル、C1−C4ハロアルキル、C1−C4アルコキシ−C1−C4−アルキル、C1−C3アルキルチオ、C1−C3ハロアルキルチオ、C1−C3アルキルスルフィニル、C1−C3ハロアルキルスルフィニル、C1−C3アルキルスルホニル又はC1−C3ハロアルキルスルホニルであり;
Y8は、C1−C4ハロアルコキシ、C2−C6ペルフルオロアルキル、C1−C6ペルフルオロアルキルチオ、C1−C6ペルフルオロアルキルスルフィニル又はC1−C6ペルフルオロアルキルスルホニルであり;
Y7は、水素、ハロゲン又はC1−C4アルキルである)である)
又は、その塩もしくはN−オキシドである。
好ましくは、A2はC−Xである。
好ましくは、A3はC−Xである。
好ましくは、A4はC−Xである。
さらに好ましくは、Xは各々独立に、水素、フッ素、メチル及びトリフルオロメチルである。
より一層好ましくは、Xは各々独立に、水素又はフッ素である。
最も好ましくは、各Xは水素である。
さらに好ましくは、R1は水素、メチル又はエチルである。
より一層好ましくは、R1は水素又はエチルである。
最も好ましくは、R1は水素である。
さらに好ましくは、R2は水素、メチル又はエチルである。
より一層好ましくは、R2は水素又はエチルである。
最も好ましくは、R2は水素である。
より好ましくは、Y1は、シアノ、塩素、臭素、メチル、トリフルオロメチルである。
さらに好ましくは、Y1は、メチル又はエチルである。
最も好ましくは、Y1はメチルである。
最も好ましくは、Y2はハロゲンである。
最も好ましくは、Y3は、ヘプタフルオロプロプ−2−イルである。
最も好ましくは、Y4は水素である。
より好ましくは、Y5は、シアノ、塩素、臭素、メチル又はトリフルオロメチルである。
さらに好ましくは、Y5はメチル又はエチルである。
最も好ましくは、Y5はメチルである。
より好ましくは、Y6は、シアノ、塩素、臭素、メチル又はトリフルオロメチルである。
さらに好ましくは、Y6はメチル又はエチルである。
最も好ましくは、Y6はメチルである。
最も好ましくは、Y7は、水素である。
最も好ましくは、Y8は、ヘプタフルオロプロプ−2−イルである。
より好ましくは、Y9は、シアノ、塩素、臭素、メチル又はトリフルオロメチルである。
さらに好ましくは、Y9はメチル又はエチルである。
最も好ましくは、Y9はメチルである。
さらに好ましい実施形態によれば、式(Ic)において、A2がC−Fであり、A1、A3、A4がCHである化合物である。
他のさらに好ましい実施形態によれば、式(Id)において、A3がC−Fであり、A1、A2、A4がCHである化合物である。
他のさらに好ましい実施形態によれば、式(Ie)において、A4がC−Fであり、A1、A2、A3がCHである化合物である。
さらに好ましい実施形態によれば、式(Ig)において、A2がC−CNであり、A1、A3、A4がCHである化合物である。
他のさらに好ましい実施形態によれば、式(Ih)において、A3がC−CNであり、A1、A2、A4がCHである化合物である。
他のさらに好ましい実施形態によれば、式(Ij)において、A4がC−CNであり、A1、A2、A3がCHである化合物である。
表2は、式(Ia)の25の化合物を提供し、ここで、Q2は2−メチル−4−ペルフルオロイソプロピル−フェニルであり、Q1は表1記載の置換基である。
表3:
表3は、式(Ia)の25の化合物を提供し、ここで、Q2は2,6−ジエチル−4−ペルフルオロイソプロピル−フェニルであり、Q1は表1記載の置換基である。
表4は、式(Ib)の25の化合物を提供し、ここで、Q2は2,6−ジメチル−4−ペルフルオロイソプロピル−フェニルであり、Q1は表1記載の置換基である。
表5は、式(Ib)の25の化合物を提供し、ここで、Q2は2−メチル−4−ペルフルオロイソプロピル−フェニルであり、Q1は表1記載の置換基である。
表6:
表6は、式(Ia)の25の化合物を提供し、ここで、Q2は2,6−ジエチル−4−ペルフルオロイソプロピル−フェニルであり、Q1は表1記載の置換基である。
表7は、式(Ic)の25の化合物を提供し、ここで、Q2は2,6−ジメチル−4−ペルフルオロイソプロピル−フェニルであり、Q1は表1記載の置換基である。
表8は、式(Ic)の25の化合物を提供し、ここで、Q2は2−メチル−4−ペルフルオロイソプロピル−フェニルであり、Q1は表1記載の置換基である。
表9:
表9は、式(Ic)の25の化合物を提供し、ここで、Q2は2,6−ジエチル−4−ペルフルオロイソプロピル−フェニルであり、Q1は表1記載の置換基である。
表10は、式(Id)の25の化合物を提供し、ここで、Q2は2,6−ジメチル−4−ペルフルオロイソプロピル−フェニルであり、Q1は表1記載の置換基である。
表11は、式(Id)の25の化合物を提供し、ここで、Q2は2−メチル−4−ペルフルオロイソプロピル−フェニルであり、Q1は表1記載の置換基である。
表12:
表12は、式(Id)の25の化合物を提供し、ここで、Q2は2,6−ジエチル−4−ペルフルオロイソプロピル−フェニルであり、Q1は表1記載の置換基である。
表13は、式(Ie)の25の化合物を提供し、ここで、Q2は2,6−ジメチル−4−ペルフルオロイソプロピル−フェニルであり、Q1は表1記載の置換基である。
表14は、式(Ie)の25の化合物を提供し、ここで、Q2は2−メチル−4−ペルフルオロイソプロピル−フェニルであり、Q1は表1記載の置換基である。
表15:
表15は、式(Ie)の25の化合物を提供し、ここで、Q2は2,6−ジエチル−4−ペルフルオロイソプロピル−フェニルであり、Q1は表1記載の置換基である。
表16は、式(If)の25の化合物を提供し、ここで、Q2は2,6−ジメチル−4−ペルフルオロイソプロピル−フェニルであり、Q1は表1記載の置換基である。
表17は、式(If)の25の化合物を提供し、ここで、Q2は2−メチル−4−ペルフルオロイソプロピル−フェニルであり、Q1は表1記載の置換基である。
表18:
表18は、式(If)の25の化合物を提供し、ここで、Q2は2,6−ジエチル−4−ペルフルオロイソプロピル−フェニルであり、Q1は表1記載の置換基である。
表19は、式(Ig)の25の化合物を提供し、ここで、Q2は2,6−ジメチル−4−ペルフルオロイソプロピル−フェニルであり、Q1は表1記載の置換基である。
表20は、式(Ig)の25の化合物を提供し、ここで、Q2は2−メチル−4−ペルフルオロイソプロピル−フェニルであり、Q1は表1記載の置換基である。
表21:
表21は、式(Ig)の25の化合物を提供し、ここで、Q2は2,6−ジエチル−4−ペルフルオロイソプロピル−フェニルであり、Q1は表1記載の置換基である。
表22は、式(Ih)の25の化合物を提供し、ここで、Q2は2,6−ジメチル−4−ペルフルオロイソプロピル−フェニルであり、Q1は表1記載の置換基である。
表23は、式(Ih)の25の化合物を提供し、ここで、Q2は2−メチル−4−ペルフルオロイソプロピル−フェニルであり、Q1は表1記載の置換基である。
表24:
表24は、式(Ih)の25の化合物を提供し、ここで、Q2は2,6−ジエチル−4−ペルフルオロイソプロピル−フェニルであり、Q1は表1記載の置換基である。
表25は、式(Ij)の25の化合物を提供し、ここで、Q2は2,6−ジメチル−4−ペルフルオロイソプロピル−フェニルであり、Q1は表1記載の置換基である。
表26は、式(Ij)の25の化合物を提供し、ここで、Q2は2−メチル−4−ペルフルオロイソプロピル−フェニルであり、Q1は表1記載の置換基である。
表27:
表27は、式(Ij)の25の化合物を提供し、ここで、Q2は2,6−ジエチル−4−ペルフルオロイソプロピル−フェニルであり、Q1は表1記載の置換基である。
1)G1及びG2が酸素である、式(I)の化合物は、式Q1−COOHのカルボン酸又は式Q1−COHal(HalはCl、FもしくはBr)のハロゲン化カルボン酸、及び、式Q2−COOHのカルボン酸又は式Q2−COHal(HalはCl、FもしくはBr)の酸ハロゲン化物を用いて、式(IV)の化合物を連続処理することにより調製することができる。ほとんどの場合、Q1とQ2をいかなる順序で導入するのが最良であるかを、当業者は決定することができ、導入するQ1とQ2の順序が逆であってもよい。
あるいは、適切な触媒/配位子系、パラジウム(0)複合体がよく用いられるが、その存在下で、アリールのハロゲン化物又はスルホン化物でアミンを処理することにより、アリール化を達成してもよい。式(V)の化合物並びに式R1−OH及びR2−OHは、既知の化合物であるか、あるいは当業者に既知の方法で作製可能である。
モモアカアブラムシ(Myzus persicae (アブラムシ))、ワタアブラムシ(Aphis gossypii (アブラムシ))、クロアブラムシ(Aphis fabae (アブラムシ))、カスミカメムシ属(Lygus spp. (カプシド(capsids)))、ホシカメムシ属(Dysdercus spp. (カプシド(capsids)))、トビイロウンカ(Nilaparvata lugens (ウンカ))、ツマグロヨコバイ(Nephotettixc incticeps (ヨコバイ))、アオカメムシ属(Nezara spp. (カメムシ))、カメムシ属(Euschistus spp. (カメムシ))、クモヘリカメムシ属(Leptocorisa spp. (カメムシ))、ミカンキイロアザミウマ(Frankliniella occidentalis (アザミウマ))、アザミウマ属(Thrips spp. (アザミウマ))、コロラドハムシ(Leptinotarsa decemlineata (コロラドハムシ))、ワタミハナゾウムシ(Anthonomus grandis (ワタミゾウムシ))、マルカイガラムシ属(Aonidiella spp. (カイガラムシ))、コナジラミ属(Trialeurodes spp. (コナジラミ))、タバココナジラミ(Bemisia tabaci (コナジラミ)), ヨーロッパアワノメイガ(Ostrinia nubilalis (European corn borer))、アフリカヨトウ(Spodoptera littoralis (cotton leafworm))、ヘリオシスヴィレセンス(Heliothis virescens (tobacco budworm))、オオタバコガ(Helicoverpa armigera (オオタバコガ))、ヘリコヴェルパゼア(Helicoverpa zea (オオタバコガ)), シレプタデロガタ(Sylepta derogata (cotton leaf roller), オオモンシロチョウ(Pieris brassicae (white butterfly)), コナガ(Plutella xylostella (コナガ))、ヤガ属(Agrotis spp. (ヨトウムシ))、ニカメイガ(Chilo suppressalis (rice stem borer))、トノサマバッタ(Locusta migratoria (バッタ))、イナゴ(Chortiocetes terminifera (バッタ))、ディアブロチカ属(Diabrotica spp. (ネキリムシ(rootworms))), リンゴハダニ(Panonychus ulmi (リンゴハダニ(European red mite))), ミカンハダニ(Panonychus citri (ンハダニ(citrus red mite))), ナミハダニ(Tetranychus urticae (ナミハダニ(two-spotted spider mite)))、ニセナミハダニ(Tetranychus cinnabarinus (ニセナミハダニ(carmine spider mite)))、ミカンサビダニ(Phyllocoptruta oleivora (citrus rust mite))、チャノホコリダニ(Polyphagotarsonemus latus (チャノホコリダニ(broad mite)))、ヒメハダニ属(Brevipalpus spp. (ヒメハダニ(flat mites)))、ウシダニ(Boophilus microplus (ウシダニ))、アメリカイヌダニ(Dermacentor variabilis (アメリカイヌダニ))、ネコノミ(Ctenocephalides felis (ネコノミ))、ハモグリバエ属(Liriomyza spp. (ハモグリバエ))、イエバエ(Musca domestica (イエバエ))、ネッタイシマカ(Aedes aegypti (カ))、ハマダラカ属(Anopheles spp. (カ))、イエカ属(Culex spp. (カ))、ルシリア属(Lucillia spp. (クロバエ))、チャバネゴキブリ(Blattella germanica (ゴキブリ))、ワモンゴキブリ(Periplaneta americana (ゴキブリ))、トウヨウゴキブリ属(Blatta orientalis (ゴキブリ))、ムカシシロアリ科のシロアリ(termites of the Mastotermitidae(例えば、ムカシシロアリ科(Mastotermes spp.))), レイビシロアリ科(the Kalotermitidae (例えば、Neotermes spp.))、ミゾガシラシロアリ科(the Rhinotermitidae (例えば、イエシロアリ(Coptotermes formosanus)、キアシシロアリ(Reticulitermes favipes)、ヤマトシロアリ(R. speratu)、R.ビルジニクス(R. virginicus)、R.ヘスペルス(R. hesperus)及びR.サントネンシス(R. santonensis)))、シロアリ科(the Termitidae (例えば、グロビテルメススルフレウス(Globitermes sulfureus))、アカカミアリ(Solenopsis geminata (ヒアリ))、イエヒメアリ(Monomorium pharaonis (イエヒメアリ(pharaoh's ant)))、ハジラミ属(Damalinia spp.)、イヌジラミ属(Linognathus spp. (biting and sucking lice))、ネコブ線虫属(Meloidogyne spp. (ネコブ線虫))、グロボデラ属(Globodera spp.)、ヘテロデラ属(Heterodera spp. (シスト線虫))、ネグサレ線虫属(Pratylenchus spp. (lesion nematodes))、ロドフォルス属(Rhodopholus spp. (banana burrowing nematodes)、チレンチュルス属(Tylenchulus spp. (シスト線虫))、粘転胃線虫属(Haemonchus contortus (barber pole worm))、シノラブディス・エレガンス(Caenorhabditis elegans(vinegar eelworm))、毛様線虫属(Trichostrongylus spp. (gastro intestinal nematodes))、ノハラナメクジ(Deroceras reticulatum (ナメクジ))がある。
a)ピレスロイド、例えばペルメトリン、シペルメトリン、フェンバレラート、エスフェンバレラート、デルタメトリン、シハロトリン(特に、ラムダ−シハロトリン)、ビフェントリン、フェンプロパトリン、シフルトリン、テフルトリン、魚安全性(fish safe)ピレスロイド(例えばエトフェンプロックス)、天然ピレトリン、テトラメトリン、s−ビオアレトリン、フェンフルトリン、パラレトリン又は5−ベンジル−3−フリルメチル−(E)−(lR,3S)−2,2−ジメチル−3−(2−オキソチオラン−3−イリデンメチル)シクロプロパンカルボキシレート;
b)有機リン酸塩、例えばプロフェノホス、スルプロフォス、アセフェート、メチルパラチオン、アジンホスメチル、ジメトン−s−メチル、ヘプテノホス(heptenophos)、チオメトン、フェナミノホス、モノクロトホス、プロフェノホス、トリアゾホス、メタミドホス、ジメトエート、ホスファミドン、マラチオン、クロルピリフォス、ホサロン、テルブホス、フェンスルホチオン、ホノホス、フォレート、ホキシム、ピリミホスメチル、ピリミホスエチル、フェニトロチオン、ホスチアゼート又はダイアジノン;
c)カルバメート(例えばアリルカルバメート)、例えばピリミカーブ、トリアザメート(triazamate)、クロエトカルブ、カルボフラン、フラチオカルブ、エチオフェンカルブ、アルジカルブ、 チオフロックス(thiofurox)、カルボスルファン、ベンダイオカルブ、フェノブカルブ、プロポクスル、メソミル又はオキサミル;
d)ベンゾイルウレア、例えばジフルベンズロン、トリフルムロン、ヘキサフルムロン、フルフェノクスロン又はクロルフルアズロン;
e)有機スズ化合物、例えばシヘキサチン、酸化フェンブタスズ又はアゾシクロチン;
f)ピラゾール、例えばテブフェンピラド及びフェンピロキシメート;
g)マクロライド、例えばエバーメクチン又はミルベマイシン、例えば、アバメクチン、エマメクチン安息香酸塩、イベルメクチン、ミルベマイシン、スピノサド又はアザジラクチン;
h)ホルモン又はフェロモン;
i)有機塩素化合物、例えばエンドスルファン、ベンゼンヘキサクロライド、DTT、クロルデン又はディルドリン;
j)アミジン、例えばクロルジメホルム又はアミトラズ;
k)燻蒸剤、例えばクロロピクリン、ジクロロプロパン、臭化メチル又はメタム(metam);
1)ネオニコチノイド化合物、例えばイミダクロプリド、チアクロプリド、アセタミプリド、ニテンピラム、ジノテフラン又はチアメトキサム;
m)ジアシルヒドラジン、例えばテブフェノジド、クロマフェノジド又はメトキシフェノジド;
n)ジフェニルエーテル、例えばジオフェノラン又はピリプロキシフェン;
o)インドキサカルブ;
p)クロルヘナピル;
q)ピメトロジン;
r)スピロテトラマト、スピロジクロフェン又はスピロメシフェン;又は
s)フルベンジアミド又はリナキシピル。
(E)−N−メチル−2−[2−(2,5−ジメチルフェノキシメチル)フェニル]−2−メトキシ−イミノアセトアミド(SSF−129)、4−ブロモ−2−シアノ−N,N−ジメチル−6−トリフルオロメチルベンズイミダゾール−1−スルホンアミド、α−[N−(3−クロロ−2,6−キシリル)−2−メトキシアセトアミド]−γ−ブチロラクトン、4−クロロ−2−シアノ−N,N−ジメチル−5−p−トリイミダゾール−1−スルホンアミド(IKF−916、シアミダゾロルスルファミド(cyamidazosulfamid)、3−5−ジクロロ−N−(3−クロロ−1−エチル−1−メチル−2−オキソプロピル)−4−メチルベンズアミド(RH−7281、ゾキサミド)、N−アリル−4,5,−ジメチル−2−トリメチルシリルチオフェン−3−カルボキサミド(MON65500)、N−(1−シアノ−1,2−ジメチルプロピル)−2−(2,4−ジクロロフェノキシ)プロピオンアミド(AC382042)、N−(2−メトキシ−5−ピリジル)−シクロプロパンカルボキサミド、アシベンゾラル(CGA245704)、アラニカブル、アルジモルフ、アニラジン、アナコナゾール、アゾキシストロビン、ベナラキシル、ベノミル、ビロクサゾール(biloxazol)、ビテルタノール、ブラストシジンS、ブロムコナゾール、ブピリメート、カプタホール、カプタン、カルベンダジム、カルベンダジムクロルヒドレート(carbendazim chlorhydrate)、カルボキシン、カルプロパミド、カルボン、CGA41396、CGA41397、キノメチオネート、クロロタロニル、クロロゾリネート(chlorozolinate)、クロジラコン(clozylacon)、銅含有化合物、例えばオキシ塩化銅、オキシキノリン酸銅(copper oxyquinolate)、硫酸銅、タール酸銅(copper tallate)及びボルドー液、シモキサニル、シプロコナゾール、シプロジニル、デバカルブ、ジ−2−ピリジルジスルフィド 1,1'−ジオキシド、ジクロフルアニド、ジクロメジン、ジクロラン、ジエトフェンカルブ、ジフェノコナゾール、ジフェンゾコート、ジフルメトリム、O,O−ジ−イソ−プロピル−S−ベンジルチオホスフェート、ジメフルアゾール、ジメトコナゾール、ジメトホルム、ジメチリモール、ジニコナゾール、ジノカップ、ジチアノン、ドデシルジメチルアンモニウムクロライド、ドデモルフ、ドジン、ドグアジン、エディフェンホス、エポキシコナゾール、エチリモール、エチル(Z)−N−ベンジルーN([メチル(メチル−チオエチリデンアミノオキシカルボニル)アミノ]チオ)−β−アラニネート、エトリジアゾール、ファモキサドン、フェンアミドン(RPA407213)、フェナリモル、フェンブコナゾール、フェンフラム(fenfuram)、フェンエヘキサミド(KBR2738)、フェンピクロニル、フェンプロピジン、フェンプロピモルフ、酢酸トリフェニルスズ(fentin acetate)、トリフフェニルスズヒドロキシド、フェルバム、フェリムゾン、フルアジナム、フルジオキソニル、フルメトバー(flumetover), フルオルイミド、フルキンコナゾール、フルジラゾール、フルトラニル、フルトリアホール、ホルペット、フベリダゾール、フララキシル、フラメトピル、グアザチン、ヘキサコナゾール、ヒドロキシイソオキサゾール、ヒメクサゾール、イマザリル、イミベンコナゾール、イミノクタジン、イミノクタジントリアセテート、イプコナソゾール、イプロベンホス、イプロジオン、イプロバリカルブ(SZX0722)、イソプロパニルブチルカルバマート、イソプロチオラン、カスガマイシン、クレソキシムメチル、LY186054、LY211795、LY248908、マンコゼブ、マンネブ、メフェノキサム、メパニピルム、メプロニル、メタラキシル、メトコナゾール、メチラム、メチラム−亜鉛(metiram-zinc)、メトミノストロビン、ミクロブタニル、ネオアソジン、ジメチルジチオカルバミド酸ニッケル、ニトロタールイソプロピル、ヌアリモル、オフレース、有機水銀化合物、オキサジキシル、オキサスルフロン、オキソリニック酸、オキスポコナゾール、オキシカルボキシン、ペフラゾエート、ペンコナゾール, ペンシクロン、フェナジンオキシド、ホスエチルアルミニウム(phosetyl-Al)、亜リン酸、フタリド、ピコキシストロビン(ZA1963)、ポリオキシンD、ポリラム、プロベナゾール、プロクロラズ、プロシミドン、プロパモカルブ、プロピコナゾール、プロピネブ、プロピオン酸、ピラゾホス、ピリフェノックス、ピリメタニル、ピロキロン、ピロキシファー(pyroxyfur)、ピロールニトリン、4級アンモニウム化合物、キノメチオネート、キノキシフェン、キントゼン、シプノコナゾール(F−155)、ナトリウムペンタクロロフェネート(sodium pentachlorophenate)、スピロキサミン、ストレプトマイシン、硫黄、テブコナゾール、テクロフタラム、テクナゼン、テトラコナゾール、チアベンザドール、チアベンダゾール、2−(チオシアノメチルチオ)ベンゾチアゾール、チオファネートメチル、チラム、チミベンコナゾール(timibenconazole)、トルクロホスメチル、トリルフルアニド、トリアジメホン、トリアジメノール、トリアズブチル(triazbutil)、トリアゾキシド(triazoxide)、トリシクラゾール、トリデモルフ、トリフロキシストロビン(CGA279202)、トリホリン、トリフルミゾール、トリチコナゾール、バリダマイシンA、バパム(vapam)、ビンクロゾリン、ジネブ及びジラムが挙げられる。
実施例I1:2−イオド−1,3−ジメチル−5−(1,2,2,2−テトラフルオロ−1−トリフルオロメチル−エチル)−ベンゼンの調製
この方法は多数の化合物の調製に使用することができる(表Aの化合物A3、表Aの化合物A23からA28、表Aの化合物A30からA32、表Aの化合物A88からA92及び表Aの化合物A93からA94)。表Aの化合物A3の合成方法を以下に述べる。他の化合物は同じ手法で調製した。
第二の選択肢:
この方法は多数の化合物の調製に、同時に使用することができる(表Aの化合物A1からA22、表Aの化合物A29、表Aの化合物A33からA86、表Aの化合物A92及び表Aの化合物A95からA112)。表Aの化合物A3の合成方法を以下に述べる。他の化合物は同じ手法で調製した。
方法A:メソッド(Water Alliance 2795 LC)で、以下のHPLCグラジエント条件である(溶媒A:0.1%ギ酸の水/アセトニトリル(9:1)、溶媒B:0.1%ギ酸添加のアセトニトリル)。
イオン化法:静電噴霧、極性:正イオン、キャピラリー(kV)3.00、コーン(V)30.00、エクストラクタ(V)2.00、イオン源温度(℃)100、脱溶媒和温度(℃)250、コーンガス流速(L/Hr)50、脱溶媒和ガス流速(UHi)400、マスレンジ:150から1000Da、DAD波長(nm):200から500。
HPLCはアジレント製:クォータナリーHPLCポンプHP1100、HP1100ダイオードアレイ検出器、HP1100サーモスタットカラムコンパーメント及びHP1100溶媒脱気装置。
グラジエント条件(溶媒A:0.04%ギ酸水溶液;溶媒B:0.05%ギ酸含有のアセトニトリル/メタノール(4:1、v/v)。
温度:60℃。
本実施例は、式(I)の化合物の殺有害生物/殺虫特性を説明する。試験は以下のものに対して行った。
コットンリーフディスクを24ウェルマイクロタイタープレートにおける寒天上に置き、試験溶液を200ppmの施用濃度となるようスプレーした。乾燥後、リーフディスクに5L1幼虫を寄生させた。サンプルを、処理から3日後に、死亡率、摂食行動及び成長制御で調べた(DAT)。以下の化合物はスポドプテラリットラリスを少なくとも80%制御したものである:
A1, A2, A3, A4, A5, A6, A7, A8, A9, A1O, A11, A12, A13, A14, A15, A16, A17, A19, A20, A21, A22, A24, A27, A35, A36, A38, A41, A42, A45, A52, A55, A72, A75, A77, A90, A91, A92, A93, A96, A97, A100, A101, A106, A107, A110, B1, B2, B3, B5, B6, B7, B12, B14, B16, C1, C2, C3, C5, C6, C7, C8, C11, D1。
人工飼料を載せた24ウェルマイクロタイタープレートに卵(0−24時間齢)を置き、施用濃度が200ppmの試験溶液を用いて(ウェル中の濃度は18ppm)ピペッティングにより処理した。4日間のインキュベーション後、サンプルの卵死亡率、幼虫死亡率及び成長制御を調べた。以下の化合物は少なくとも80%のニセアメリカタバコガニの抑制を示した:
A1, A2, A3, A4, A5, A6, A7, A8, A9, A1O, A11, A12, A13, A14, A15, A16, A17, A18, A21, A22, A23, A27, A28, A30, A33, A37, A38, A55, A58, A72, A89, A91, A92, A93, A95, A96, A97, A1OO, A1O1, A103, A104, A107, A108, A109, A11O, B1, B2, B3, B4, B5, B6, B7, B8, B12, B13, B14, B16, C1, C2, C3, C5, C6, C7, C8, C9, C11, D1。
人工飼料を載せた24ウェルマイクロタイタープレート(MTP)を、施用濃度が200ppmの試験溶液を用いて(ウェル中の濃度は18ppm)ピペッティングにより処理した。乾燥後、MTP上にL2幼虫を寄生させた(1ウェル当たり6−10)。6日間のインキュベーションの後、サンプルの幼虫死亡率及び成長制御を調べた。以下の化合物は少なくとも80%のプルテラキシロステラの抑制を示した:
A1, A2, A3, A4, A5, A6, A7, A8, A14, A15, A17, A26, A27, A89, A91, A92, A93, A95, B1, B3, B5, B6, B7, B13, B14, C1, C2, C3, C5, C6, C7, D1。
人工飼料を載せた24ウェルマイクロタイタープレート(MTP)を、施用濃度が200ppmの試験溶液を用いて(ウェル中の濃度は18ppm)ピペッティングにより処理した。乾燥後、MTP上にL2幼虫を寄生させた(1ウェル当たり6−10)。5日間のインキュベーションの後、サンプルの幼虫死亡率及び成長制御を調べた。以下の化合物は少なくとも80%のディアブロチカバルテアタの抑制を示した:
A1, A2, A3, A5, A6, A7, A8, A1O, A11, A14, A15, A17, A26, A27, A38, A89, A90, A91, A92, A93, A95, A97, A103, A108, B1, B3, B6, B7, B12, B14, C1, C3, C5, C6, D1。
10−15のネッタイシマカ幼虫(L2)と栄養分の混合物を、96ウェルマイクロタイタープレートに置いた。施用濃度2ppmで試験溶液をウェルに注入した。2日後、虫の死亡率及び成長制御を調べた。以下の化合物は少なくとも80%のネッタイシマカの抑制を示した:
A1, A2, A3, A6, A8, A14, A15, A16, A18, A23, A26, A27, B1。
Claims (17)
- 式(I)の化合物、
Xは各々独立に水素、ハロゲン、シアノ、C1−C4アルキル、C1−C4ハロアルキル又はC1−C4アルコキシであり;
R1及びR2は、互いに独立に水素、C1−C4アルキル又はC1−C4アルキルカルボニルであり;
G1及びG2は、互いに独立に酸素又は硫黄であり;
Q1は、アリールもしくは1〜5の置換基R3で置換されたアリールであり、R3は同種でも異種でもよく、又は、Q1はヘテロシクリルもしくは1〜5の置換基R3で置換されたヘテロシクリルであり、R3は同種でも異種でもよく、ここで、
R3は各々独立にシアノ、ニトロ、ヒドロキシ、ハロゲン、C1−C4アルキル、C1−C4ハロアルキル、C2−C4アルケニル、C2−C4ハロアルケニル、C2−C4アルキニル、C2−C4ハロアルキニル、C3−C6シクロアルキル、C3−C6ハロシクロアルキル、C1−C3アルコキシ、C1−C3ハロアルコキシ、C1−C3アルキルチオ、C1−C3ハロアルキルチオ、C1−C3アルキルスルフィニル、C1−C3ハロアルキルスルフィニル、C1−C3アルキルスルホニル、C1−C3ハロアルキルスルホニル、アミノ、C1−C4アルキルアミノ、ジ−(C1−C4アルキル)アミノ、C1−C4アルキルカルボニル、C1−C4アルキルカルボニルオキシ、C1−C4アルコキシカルボニル、C1−C4アルキルカルボニルアミノ、又は、ハロゲン、C1−C4アルキル、C1−C4ハロアルキル、C1−C4アルコキシもしくはC1−C4ハロアルコキシから独立に選択される1〜3の置換基によって置換されていてもよいアリール、又は、ハロゲン、C1−C4アルキル、C1−C4ハロアルキル、C1−C4アルコキシもしくはC1−C4ハロアルコキシから独立に選択される1〜3の置換基によって置換されていてもよいヘテロアリールであり;
Q2は、式(II)又は(III)部分、
Y1及びY5は、各々独立に、水素、シアノ、ハロゲン、C1−C4アルキル、C1−C4ハロアルキル、C1−C4アルコキシ−C1−C4−アルキル、C1−C3アルキルチオ、C1−C3ハロアルキルチオ、C1−C3アルキルスルフィニル、C1−C3ハロアルキルスルフィニル、C1−C3アルキルスルホニル又はC1−C3ハロアルキルスルホニルであり;
Y3は、C2−C6ペルフルオロアルキル、C1−C6ペルフルオロアルキルチオ、C1−C6ペルフルオロアルキルスルフィニル又はC1−C6ペルフルオロアルキルスルホニルであり;
Y2及びY4は、各々独立に、水素、ハロゲン又はC1−C4アルキルであり;
Y6及びY9は、各々独立に、水素、シアノ、ハロゲン、C1−C4アルキル、C1−C4ハロアルキル、C1−C4アルコキシ−C1−C4−アルキル、C1−C3アルキルチオ、C1−C3ハロアルキルチオ、C1−C3アルキルスルフィニル、C1−C3ハロアルキルスルフィニル、C1−C3アルキルスルホニル又はC1−C3ハロアルキルスルホニルであり;
Y8は、C1−C4ハロアルコキシ、C2−C6ペルフルオロアルキル、C1−C6ペルフルオロアルキルチオ、C1−C6ペルフルオロアルキルスルフィニル又はC1−C6ペルフルオロアルキルスルホニルであり;
Y7は、水素、ハロゲン又はC1−C4アルキルである)である)
又は、その塩もしくはN−オキシド。 - A1がC−Xである、請求項1記載の化合物。
- A2がC−Xである、請求項1又は請求項2記載の化合物。
- A3がC−Xである、請求項1〜3のいずれか1項に記載の化合物。
- A4がC−Xである、請求項1〜4のいずれか1項に記載の化合物。
- 各Xが独立に、水素、フッ素、塩素、臭素、シアノ、メチル、トリフルオロメチル又はメトキシである、請求項1〜5のいずれか1項に記載の化合物。
- R1が、水素、メチル、エチル又はアセチルである、請求項1〜6のいずれか1項に記載の化合物。
- R2が、水素、メチル、エチル又はアセチルである、請求項1〜7のいずれか1項に記載の化合物。
- G1が、酸素である、請求項1〜8のいずれか1項に記載の化合物。
- G2が、酸素である、請求項1〜9のいずれか1項に記載の化合物。
- Q1が、フェニル、ピリジル、ピリミジル、フラニル、チオフェニル、オキサゾリル、イソオキサゾリル、チアゾリル、チアジアゾリル、ピロリル、ピラゾリルもしくはイミダゾリル、又は、シアノ、ニトロ、ヒドロキシ、フルオロ、クロロ、ブロモ、メチル、トリフルオロメチル、メトキシ、メチルチオ、メチルスルフィニル、メチルスルホニルもしくはフェニルから独立に選択される1〜4の置換基によって置換される、フェニル、ピリジル、ピリミジル、フラニル、チオフェニル、オキサゾリル、イソオキサゾリル、チアゾリル、チアジアゾリル、ピロリル、ピラゾリルもしくはイミダゾリルである、請求項1〜10のいずれか1項記載の化合物。
- Q2が、式(II)部分である、請求項1〜11のいずれか1項記載の化合物。
- Q2が、2,6−ジメチル−4−ペルフルオロイソプロピル−フェニルである、請求項1〜11のいずれか1項記載の化合物。
- Q2が、2,6−ジエチル−4−ペルフルオロイソプロピル−フェニルである、請求項1〜11のいずれか1項記載の化合物。
- 虫、ダニ、線虫又は軟体動物を、駆除及び抑制する方法であって、請求項1〜14のいずれか1項に記載の式(I)の化合物を、有害生物、有害生物の存在場所又は有害生物による攻撃を受け易い植物に対し、殺虫的、殺ダニ的、殺線虫的又は殺軟体動物的有効量を施用することを含んでなる方法。
- 殺虫、殺ダニ、殺線虫又は殺軟体動物組成物であって、請求項1〜14のいずれか1項に記載の式(I)の化合物を、殺虫的、殺ダニ的、殺線虫的又は殺軟体動物的有効量含んでなる組成物。
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JP2016503403A (ja) * | 2012-11-03 | 2016-02-04 | ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング | サイトメガロウイルスの阻害剤 |
JPWO2013191041A1 (ja) * | 2012-06-22 | 2016-05-26 | 住友化学株式会社 | アミド化合物及びその有害生物防除用途 |
JP2017502038A (ja) * | 2013-12-23 | 2017-01-19 | シンジェンタ パーティシペーションズ アーゲー | 殺虫性化合物 |
JP2020534334A (ja) * | 2017-09-20 | 2020-11-26 | 三井化学アグロ株式会社 | 動物用外部寄生虫長期防除剤 |
Families Citing this family (13)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB0907823D0 (en) * | 2009-05-06 | 2009-06-17 | Syngenta Participations Ag | Insecticidal compounds |
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EP2253617A1 (de) | 2009-05-20 | 2010-11-24 | Bayer CropScience AG | Halogen-substituierte Verbindungen als Pestizide |
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GB201317609D0 (en) | 2013-10-04 | 2013-11-20 | Cancer Rec Tech Ltd | Inhibitor compounds |
GB201505658D0 (en) * | 2015-04-01 | 2015-05-13 | Cancer Rec Tech Ltd | Inhibitor compounds |
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CN114751841B (zh) * | 2022-05-31 | 2023-07-11 | 重庆文理学院 | N-(3-(3-氯苯甲酰胺)苯基)-4-甲氧基-3-硝基苯甲酰胺及其制备方法与应用 |
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Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1998020878A1 (en) * | 1995-03-02 | 1998-05-22 | Fmc Corporation | 5-[φ-(SUBSTITUTED ARYL)ALKENYLENE AND ALKYNYLENE]-2,4-DIAMINOPYRIMIDINES AS PESTICIDES |
JP2002522421A (ja) * | 1998-08-04 | 2002-07-23 | アストラゼネカ アクチボラグ | サイトカイン産生の阻害剤として有用なアミド誘導体 |
JP2003528070A (ja) * | 2000-03-22 | 2003-09-24 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー | 殺虫性アントラニルアミド類 |
Family Cites Families (43)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB9816837D0 (en) | 1998-08-04 | 1998-09-30 | Zeneca Ltd | Amide derivatives |
US5629124A (en) | 1995-01-31 | 1997-05-13 | Mitsubishi Chemical Corporation | Charge controlling agent for electrostatic image development, and toner and charge-imparting material employing it |
EP0848700B1 (de) | 1995-08-30 | 2003-07-02 | Bayer CropScience AG | Acylaminosalicylsäureamide und ihre verwendung als schädlingsbekämpfungsmittel |
JPH09278731A (ja) | 1996-04-04 | 1997-10-28 | Otsuka Chem Co Ltd | 5−ニトロサリチル酸アニリド誘導体、それを有効成分として含む植物病害防除剤 |
DE19710609A1 (de) | 1997-03-14 | 1998-09-17 | Bayer Ag | Substituierte Aminosalicylsäureamide |
BR9814327A (pt) | 1997-12-23 | 2000-10-03 | Warner Lambert Co | Compostos de tiouréia e benzamida, composições e pro-cessos para tratamento ou prevenção de doenças infla-matórias e arteriosclerose |
AU3665199A (en) | 1998-04-29 | 1999-11-16 | Vertex Pharmaceuticals Incorporated | Inhibitors of impdh enzyme |
AU731777B2 (en) | 1998-11-30 | 2001-04-05 | Nihon Nohyaku Co., Ltd. | Aniline derivative and process for producing the same |
YU42401A (sh) | 1998-12-14 | 2003-12-31 | Ortho-Mcneil Pharmaceuticals Inc. | Supstituisani heterociklični acil-tripeptidi korisni kao modulatori receptora trombina |
JP2002539187A (ja) | 1999-03-17 | 2002-11-19 | アストラゼネカ アクチボラグ | アミド誘導体 |
CZ2002487A3 (cs) * | 1999-08-20 | 2002-06-12 | Dow Agrosciences Llc | Fungicidní heterocyklické aromatické amidy, prostředky na jejich bázi, způsoby jejich pouľití a přípravy |
WO2001019788A2 (en) | 1999-09-17 | 2001-03-22 | Cor Therapeutics, Inc. | BENZAMIDES AND RELATED INHIBITORS OF FACTOR Xa |
WO2001021160A2 (en) * | 1999-09-23 | 2001-03-29 | Axxima Pharmaceuticals Aktiengesellschaft | Carboxymide and aniline derivatives as selective inhibitors of pathogens |
PL356481A1 (en) | 1999-12-22 | 2004-06-28 | Nihon Nohyaku Co, Ltd. | Aromatic diamide derivatives, chemicals for agricultural or horticultural use and usage thereof |
KR20020077414A (ko) | 2000-02-04 | 2002-10-11 | 니혼노야쿠가부시키가이샤 | 퍼플루오로이소프로필벤젠 유도체 |
EP1275653A1 (en) | 2001-07-10 | 2003-01-15 | Bayer CropScience S.A. | Oxazolopyridines and their use as fungicides |
WO2003011028A1 (en) | 2001-08-01 | 2003-02-13 | Nissan Chemical Industries, Ltd. | Substituted amides and pest controllers |
SE0102764D0 (sv) | 2001-08-17 | 2001-08-17 | Astrazeneca Ab | Compounds |
WO2004043335A2 (en) | 2001-09-13 | 2004-05-27 | Genesoft, Inc. | Methods of treating infection by drug resistant bacteria |
WO2004006906A2 (en) | 2002-07-15 | 2004-01-22 | Combinatorx, Incorporated | Methods for the treatment of neoplasms |
WO2004018410A1 (ja) | 2002-08-26 | 2004-03-04 | Nissan Chemical Industries, Ltd. | 置換ベンズアニリド化合物及び有害生物防除剤 |
US7501530B2 (en) | 2003-03-24 | 2009-03-10 | Basf Aktiengesellschaft | Trifluoromethyl-thiophene carboxylic acid aniledes and use thereof as fungicides |
CN101684079B (zh) | 2003-08-29 | 2013-04-03 | 三井化学株式会社 | 农园艺用杀虫剂的制备中间体及制备方法 |
KR101172322B1 (ko) | 2003-12-26 | 2012-08-14 | 산텐 세이야꾸 가부시키가이샤 | 저면 필터를 가지는 액체 수용 용기 |
GB0412468D0 (en) | 2004-06-04 | 2004-07-07 | Astrazeneca Ab | Chemical compounds |
MX2007002819A (es) * | 2004-09-09 | 2007-08-14 | Natco Pharma Ltd | Nuevos derivados de fenilaminopirimidina como inhibidores de bcl-abl cinasa. |
JP4679925B2 (ja) | 2005-02-18 | 2011-05-11 | 三井化学アグロ株式会社 | 殺虫剤の製造方法及びその製造中間体 |
JP2006306850A (ja) | 2005-03-29 | 2006-11-09 | Nissan Chem Ind Ltd | 置換ベンズアニリド化合物及び有害生物防除剤 |
JP2006306771A (ja) | 2005-04-28 | 2006-11-09 | Mitsui Chemicals Inc | 農園芸用殺虫剤 |
US8067638B2 (en) | 2005-06-21 | 2011-11-29 | Mitsui Chemicals, Inc. | Amide derivative and insecticide containing the same |
AU2006260237A1 (en) | 2005-06-23 | 2006-12-28 | Mitsui Chemicals, Inc. | Amide derivative, pesticide containing such compound and use thereof |
JP4580836B2 (ja) | 2005-07-25 | 2010-11-17 | 三井化学アグロ株式会社 | 殺虫殺菌組成物 |
CA2616749C (en) | 2005-07-27 | 2012-01-03 | Mitsui Chemicals, Inc. | Composition for preventing harmful organisms |
JP2007031395A (ja) | 2005-07-29 | 2007-02-08 | Bayer Cropscience Ag | 殺虫性3−アシルアミノベンズアニリド類 |
US7754717B2 (en) | 2005-08-15 | 2010-07-13 | Amgen Inc. | Bis-aryl amide compounds and methods of use |
JP2007099761A (ja) | 2005-09-08 | 2007-04-19 | Mitsui Chemicals Inc | アミド誘導体ならびにその殺虫剤としての使用方法 |
JP2007119416A (ja) | 2005-10-31 | 2007-05-17 | Bayer Cropscience Ag | 殺虫性2−アシルアミノチアゾール−4−カルボキサミド類 |
BRPI0619980A2 (pt) | 2005-12-15 | 2014-10-14 | Nihon Nohyaku Co Ltd | Derivados de ftalamida e de anilina, inseticida agrícola ou hortícula, e, método de uso do mesmo |
WO2007083394A1 (ja) | 2006-01-19 | 2007-07-26 | Mitsui Chemicals, Inc. | ジアミン誘導体を含む有害生物防除組成物 |
BRPI0710751A2 (pt) | 2006-04-28 | 2011-06-14 | Syngenta Participations Ag | composto, mÉtodo de combater e controlar insetos, acarinos, nematàdeos ou moluscos, e, composiÇço inseticida, acaridica ou nematicida |
JP4884072B2 (ja) | 2006-05-12 | 2012-02-22 | 三井化学アグロ株式会社 | 複素環誘導体ならびにその殺虫剤としての使用方法 |
GB0612713D0 (en) | 2006-06-27 | 2006-08-09 | Syngenta Participations Ag | Insecticidal compounds |
GB0614691D0 (en) | 2006-07-24 | 2006-08-30 | Syngenta Participations Ag | Insecticidal compounds |
-
2007
- 2007-09-07 JP JP2009527061A patent/JP5296688B2/ja not_active Expired - Fee Related
- 2007-09-07 EP EP07818071A patent/EP2069287A1/en not_active Withdrawn
- 2007-09-07 US US12/440,895 patent/US8466180B2/en not_active Expired - Fee Related
- 2007-09-07 BR BRPI0716560-9A2A patent/BRPI0716560A2/pt not_active IP Right Cessation
- 2007-09-07 WO PCT/EP2007/007813 patent/WO2008031534A1/en active Application Filing
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1998020878A1 (en) * | 1995-03-02 | 1998-05-22 | Fmc Corporation | 5-[φ-(SUBSTITUTED ARYL)ALKENYLENE AND ALKYNYLENE]-2,4-DIAMINOPYRIMIDINES AS PESTICIDES |
JP2002522421A (ja) * | 1998-08-04 | 2002-07-23 | アストラゼネカ アクチボラグ | サイトカイン産生の阻害剤として有用なアミド誘導体 |
JP2003528070A (ja) * | 2000-03-22 | 2003-09-24 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー | 殺虫性アントラニルアミド類 |
Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
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JPWO2013191041A1 (ja) * | 2012-06-22 | 2016-05-26 | 住友化学株式会社 | アミド化合物及びその有害生物防除用途 |
JP2016503403A (ja) * | 2012-11-03 | 2016-02-04 | ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング | サイトメガロウイルスの阻害剤 |
JP2017502038A (ja) * | 2013-12-23 | 2017-01-19 | シンジェンタ パーティシペーションズ アーゲー | 殺虫性化合物 |
USRE49022E1 (en) | 2013-12-23 | 2022-04-12 | Syngenta Participations Ag | Insecticidal compounds |
JP2020534334A (ja) * | 2017-09-20 | 2020-11-26 | 三井化学アグロ株式会社 | 動物用外部寄生虫長期防除剤 |
JP7277445B2 (ja) | 2017-09-20 | 2023-05-19 | 三井化学クロップ&ライフソリューション株式会社 | 動物用外部寄生虫長期防除剤 |
Also Published As
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US8466180B2 (en) | 2013-06-18 |
BRPI0716560A2 (pt) | 2013-10-01 |
US20100076078A1 (en) | 2010-03-25 |
JP5296688B2 (ja) | 2013-09-25 |
EP2069287A1 (en) | 2009-06-17 |
WO2008031534A1 (en) | 2008-03-20 |
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