TW201117721A - Pesticidal carboxamides - Google Patents
Pesticidal carboxamides Download PDFInfo
- Publication number
- TW201117721A TW201117721A TW99126824A TW99126824A TW201117721A TW 201117721 A TW201117721 A TW 201117721A TW 99126824 A TW99126824 A TW 99126824A TW 99126824 A TW99126824 A TW 99126824A TW 201117721 A TW201117721 A TW 201117721A
- Authority
- TW
- Taiwan
- Prior art keywords
- alkyl
- group
- ffi
- haloalkyl
- aryl
- Prior art date
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- 150000003857 carboxamides Chemical class 0.000 title abstract 3
- 230000000361 pesticidal effect Effects 0.000 title abstract 2
- 125000001424 substituent group Chemical group 0.000 claims abstract description 41
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 32
- 244000000054 animal parasite Species 0.000 claims abstract description 4
- 239000000575 pesticide Substances 0.000 claims abstract 3
- 125000000217 alkyl group Chemical group 0.000 claims description 593
- -1 mercapto, fluorenyl Chemical group 0.000 claims description 419
- 150000001875 compounds Chemical class 0.000 claims description 200
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 120
- 125000000623 heterocyclic group Chemical group 0.000 claims description 94
- 229910052739 hydrogen Inorganic materials 0.000 claims description 68
- 125000003118 aryl group Chemical group 0.000 claims description 67
- 239000001257 hydrogen Substances 0.000 claims description 64
- 125000001188 haloalkyl group Chemical group 0.000 claims description 56
- 229910052736 halogen Inorganic materials 0.000 claims description 49
- 150000002367 halogens Chemical class 0.000 claims description 44
- 125000003545 alkoxy group Chemical group 0.000 claims description 43
- 150000001412 amines Chemical class 0.000 claims description 43
- 150000002431 hydrogen Chemical group 0.000 claims description 36
- 239000000460 chlorine Substances 0.000 claims description 33
- 229910052757 nitrogen Inorganic materials 0.000 claims description 33
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 32
- 229910052799 carbon Inorganic materials 0.000 claims description 30
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 30
- 125000005843 halogen group Chemical group 0.000 claims description 30
- 150000001721 carbon Chemical group 0.000 claims description 27
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 22
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 21
- 229910052717 sulfur Inorganic materials 0.000 claims description 20
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 19
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 18
- 229920006395 saturated elastomer Polymers 0.000 claims description 18
- 125000005347 halocycloalkyl group Chemical group 0.000 claims description 16
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 15
- 150000002923 oximes Chemical class 0.000 claims description 14
- 125000003342 alkenyl group Chemical group 0.000 claims description 13
- 125000003277 amino group Chemical group 0.000 claims description 12
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 12
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 12
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 12
- 125000004434 sulfur atom Chemical group 0.000 claims description 12
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 11
- BPFZRKQDXVZTFD-UHFFFAOYSA-N disulfur decafluoride Chemical compound FS(F)(F)(F)(F)S(F)(F)(F)(F)F BPFZRKQDXVZTFD-UHFFFAOYSA-N 0.000 claims description 11
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 11
- 229910052760 oxygen Inorganic materials 0.000 claims description 11
- 239000001301 oxygen Substances 0.000 claims description 11
- 125000003396 thiol group Chemical class [H]S* 0.000 claims description 11
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 claims description 10
- 125000000304 alkynyl group Chemical group 0.000 claims description 10
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 10
- 229910052796 boron Inorganic materials 0.000 claims description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 9
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 9
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 9
- 239000000126 substance Substances 0.000 claims description 9
- 239000011593 sulfur Substances 0.000 claims description 9
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 8
- 125000005842 heteroatom Chemical group 0.000 claims description 8
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 7
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims description 6
- 150000001408 amides Chemical class 0.000 claims description 6
- 125000005129 aryl carbonyl group Chemical group 0.000 claims description 6
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 6
- 125000002837 carbocyclic group Chemical group 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 125000000232 haloalkynyl group Chemical group 0.000 claims description 6
- 239000002917 insecticide Substances 0.000 claims description 6
- 229910052707 ruthenium Inorganic materials 0.000 claims description 6
- 239000002689 soil Substances 0.000 claims description 6
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 5
- 125000006769 halocycloalkoxy group Chemical group 0.000 claims description 5
- 125000006517 heterocyclyl carbonyl group Chemical group 0.000 claims description 5
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 5
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 4
- 125000000262 haloalkenyl group Chemical group 0.000 claims description 4
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 3
- 208000036822 Small cell carcinoma of the ovary Diseases 0.000 claims description 3
- 125000004414 alkyl thio group Chemical group 0.000 claims description 3
- 125000004995 haloalkylthio group Chemical group 0.000 claims description 3
- VMGAPWLDMVPYIA-HIDZBRGKSA-N n'-amino-n-iminomethanimidamide Chemical compound N\N=C\N=N VMGAPWLDMVPYIA-HIDZBRGKSA-N 0.000 claims description 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 3
- 201000005292 ovarian small cell carcinoma Diseases 0.000 claims description 3
- BOLDJAUMGUJJKM-LSDHHAIUSA-N renifolin D Natural products CC(=C)[C@@H]1Cc2c(O)c(O)ccc2[C@H]1CC(=O)c3ccc(O)cc3O BOLDJAUMGUJJKM-LSDHHAIUSA-N 0.000 claims description 3
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 2
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims description 2
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 2
- 125000006569 (C5-C6) heterocyclic group Chemical group 0.000 claims description 2
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 claims description 2
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 2
- 125000004440 haloalkylsulfinyl group Chemical group 0.000 claims description 2
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims description 2
- 125000000717 hydrazino group Chemical group [H]N([*])N([H])[H] 0.000 claims description 2
- 230000000670 limiting effect Effects 0.000 claims description 2
- 125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 claims description 2
- 241000894007 species Species 0.000 claims description 2
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 3
- 125000004441 haloalkylsulfonyl group Chemical group 0.000 claims 2
- 101000654316 Centruroides limpidus Beta-toxin Cll2 Proteins 0.000 claims 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims 1
- NQHAZTDQFIYTQD-UHFFFAOYSA-N SOS Chemical compound SOS NQHAZTDQFIYTQD-UHFFFAOYSA-N 0.000 claims 1
- 241000239226 Scorpiones Species 0.000 claims 1
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 claims 1
- 150000001345 alkine derivatives Chemical class 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 150000004820 halides Chemical class 0.000 claims 1
- 125000005343 heterocyclic alkyl group Chemical group 0.000 claims 1
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 1
- 239000010977 jade Substances 0.000 claims 1
- 239000000463 material Substances 0.000 claims 1
- 125000004076 pyridyl group Chemical group 0.000 claims 1
- 238000006467 substitution reaction Methods 0.000 claims 1
- RSPCKAHMRANGJZ-UHFFFAOYSA-N thiohydroxylamine Chemical compound SN RSPCKAHMRANGJZ-UHFFFAOYSA-N 0.000 claims 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 370
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 236
- 101150041968 CDC13 gene Proteins 0.000 description 234
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- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 103
- 238000005481 NMR spectroscopy Methods 0.000 description 92
- 239000000243 solution Substances 0.000 description 80
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- 238000006243 chemical reaction Methods 0.000 description 67
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- 238000012360 testing method Methods 0.000 description 55
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- 238000000034 method Methods 0.000 description 46
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 46
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 14
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- 150000003457 sulfones Chemical class 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 230000000153 supplemental effect Effects 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 229920001059 synthetic polymer Polymers 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 125000005888 tetrahydroindolyl group Chemical group 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 125000005323 thioketone group Chemical group 0.000 description 1
- GZNAASVAJNXPPW-UHFFFAOYSA-M tin(4+) chloride dihydrate Chemical compound O.O.[Cl-].[Sn+4] GZNAASVAJNXPPW-UHFFFAOYSA-M 0.000 description 1
- FWPIDFUJEMBDLS-UHFFFAOYSA-L tin(II) chloride dihydrate Substances O.O.Cl[Sn]Cl FWPIDFUJEMBDLS-UHFFFAOYSA-L 0.000 description 1
- KJAMZCVTJDTESW-UHFFFAOYSA-N tiracizine Chemical compound C1CC2=CC=CC=C2N(C(=O)CN(C)C)C2=CC(NC(=O)OCC)=CC=C21 KJAMZCVTJDTESW-UHFFFAOYSA-N 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 239000011573 trace mineral Substances 0.000 description 1
- 235000013619 trace mineral Nutrition 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- ILJSQTXMGCGYMG-UHFFFAOYSA-N triacetic acid Chemical compound CC(=O)CC(=O)CC(O)=O ILJSQTXMGCGYMG-UHFFFAOYSA-N 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 description 1
- 125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- MFLLMKMFWIUACU-UHFFFAOYSA-N trifluoromethanethiol Chemical compound FC(F)(F)S MFLLMKMFWIUACU-UHFFFAOYSA-N 0.000 description 1
- 235000019798 tripotassium phosphate Nutrition 0.000 description 1
- 229910000404 tripotassium phosphate Inorganic materials 0.000 description 1
- 235000013976 turmeric Nutrition 0.000 description 1
- 239000004474 valine Substances 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
Classifications
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- 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
- C07C233/66—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 halogen atoms or by nitro or nitroso groups
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- A01N37/42—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing within the same carbon skeleton a carboxylic group or a thio analogue, or a derivative thereof, and a carbon atom having only two bonds to hetero atoms with at the most one bond to halogen, e.g. keto-carboxylic acids
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- A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
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- C07C235/70—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups and doubly-bound oxygen atoms bound to the same carbon skeleton
- C07C235/84—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups and doubly-bound oxygen atoms bound to the same carbon skeleton with the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a six-membered aromatic ring
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- C07C237/28—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a non-condensed six-membered aromatic ring of the carbon skeleton
- C07C237/40—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a non-condensed six-membered aromatic ring of the carbon skeleton having the nitrogen atom of the carboxamide group bound to a carbon atom of a six-membered aromatic ring
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- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
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-
2010
- 2010-03-12 JP JP2010055470A patent/JP2011057661A/ja active Pending
- 2010-08-03 IN IN1350DEN2012 patent/IN2012DN01350A/en unknown
- 2010-08-03 EP EP16196800.3A patent/EP3153497A3/en not_active Withdrawn
- 2010-08-03 KR KR20127006084A patent/KR20120048006A/ko not_active Withdrawn
- 2010-08-03 CN CN201080045858XA patent/CN102574777A/zh active Pending
- 2010-08-03 BR BR112012003068A patent/BR112012003068A2/pt not_active IP Right Cessation
- 2010-08-03 EP EP10745140A patent/EP2464624A2/en not_active Withdrawn
- 2010-08-03 CA CA2770801A patent/CA2770801A1/en not_active Abandoned
- 2010-08-03 JP JP2012524130A patent/JP2013501737A/ja active Pending
- 2010-08-03 AU AU2010281898A patent/AU2010281898A1/en not_active Abandoned
- 2010-08-03 US US13/390,302 patent/US9227923B2/en active Active
- 2010-08-03 MX MX2012001787A patent/MX2012001787A/es not_active Application Discontinuation
- 2010-08-03 WO PCT/EP2010/004739 patent/WO2011018170A2/en active Application Filing
- 2010-08-03 NZ NZ598122A patent/NZ598122A/xx not_active IP Right Cessation
- 2010-08-05 UY UY32832A patent/UY32832A/es not_active Application Discontinuation
- 2010-08-11 AR ARP100102944 patent/AR077853A1/es unknown
- 2010-08-12 TW TW99126824A patent/TW201117721A/zh unknown
Also Published As
Publication number | Publication date |
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JP2013501737A (ja) | 2013-01-17 |
NZ598122A (en) | 2013-09-27 |
IN2012DN01350A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 2015-06-05 |
US20120149910A1 (en) | 2012-06-14 |
BR112012003068A2 (pt) | 2016-08-16 |
WO2011018170A2 (en) | 2011-02-17 |
AU2010281898A1 (en) | 2012-02-02 |
AR077853A1 (es) | 2011-09-28 |
MX2012001787A (es) | 2012-02-29 |
WO2011018170A3 (en) | 2011-08-11 |
CA2770801A1 (en) | 2011-02-17 |
EP3153497A3 (en) | 2017-07-05 |
JP2011057661A (ja) | 2011-03-24 |
KR20120048006A (ko) | 2012-05-14 |
EP3153497A2 (en) | 2017-04-12 |
US9227923B2 (en) | 2016-01-05 |
CN102574777A (zh) | 2012-07-11 |
EP2464624A2 (en) | 2012-06-20 |
UY32832A (es) | 2011-03-31 |
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