TWI359143B - Novel insecticides - Google Patents

Info

Publication number

TWI359143B

TWI359143B TW094143118A TW94143118A TWI359143B TW I359143 B TWI359143 B TW I359143B TW 094143118 A TW094143118 A TW 094143118A TW 94143118 A TW94143118 A TW 94143118A TW I359143 B TWI359143 B TW I359143B

Authority

TW

Taiwan

Prior art keywords

group

alkyl

alkoxy

spp

cvc6

Prior art date

2004-12-09

Links

• Espacenet
• Global Dossier
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• 239000002917 insecticide Substances 0.000 title description 3
• 150000001875 compounds Chemical class 0.000 claims description 249
• -1 alkane sulfonate Chemical class 0.000 claims description 106
• 239000000203 mixture Substances 0.000 claims description 69
• 125000000217 alkyl group Chemical group 0.000 claims description 61
• OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 58
• 150000003839 salts Chemical class 0.000 claims description 52
• 239000004480 active ingredient Substances 0.000 claims description 49
• 125000003545 alkoxy group Chemical group 0.000 claims description 43
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 42
• 229910052717 sulfur Inorganic materials 0.000 claims description 38
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 35
• 229910052760 oxygen Inorganic materials 0.000 claims description 35
• 239000001301 oxygen Substances 0.000 claims description 35
• 239000011593 sulfur Substances 0.000 claims description 34
• 229910052736 halogen Inorganic materials 0.000 claims description 31
• 150000002367 halogens Chemical class 0.000 claims description 30
• 238000000034 method Methods 0.000 claims description 25
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 25
• 125000004414 alkyl thio group Chemical group 0.000 claims description 23
• 125000001188 haloalkyl group Chemical group 0.000 claims description 23
• 239000007789 gas Substances 0.000 claims description 18
• 125000004438 haloalkoxy group Chemical group 0.000 claims description 17
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 16
• 125000001424 substituent group Chemical group 0.000 claims description 16
• 125000000304 alkynyl group Chemical group 0.000 claims description 14
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 14
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 12
• 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 12
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 12
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 12
• 125000005347 halocycloalkyl group Chemical group 0.000 claims description 12
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 11
• 241000607479 Yersinia pestis Species 0.000 claims description 11
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 11
• 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 11
• 125000004995 haloalkylthio group Chemical group 0.000 claims description 11
• 125000003342 alkenyl group Chemical group 0.000 claims description 10
• 239000001257 hydrogen Substances 0.000 claims description 10
• 229910052739 hydrogen Inorganic materials 0.000 claims description 10
• 239000000463 material Substances 0.000 claims description 10
• 125000006310 cycloalkyl amino group Chemical group 0.000 claims description 9
• 239000005864 Sulphur Substances 0.000 claims description 8
• 125000003282 alkyl amino group Chemical group 0.000 claims description 8
• 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 8
• 125000003396 thiol group Chemical class [H]S* 0.000 claims description 8
• 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims description 7
• 241001124076 Aphididae Species 0.000 claims description 6
• 150000001412 amines Chemical class 0.000 claims description 6
• 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 6
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 5
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 5
• QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 5
• 239000002671 adjuvant Substances 0.000 claims description 5
• 125000004122 cyclic group Chemical group 0.000 claims description 5
• 125000004663 dialkyl amino group Chemical group 0.000 claims description 5
• 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 5
• 229910021653 sulphate ion Inorganic materials 0.000 claims description 5
• 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 4
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
• UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 claims description 4
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
• 125000005265 dialkylamine group Chemical group 0.000 claims description 4
• NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims description 4
• 125000000262 haloalkenyl group Chemical group 0.000 claims description 4
• 150000002431 hydrogen Chemical class 0.000 claims description 4
• 125000004434 sulfur atom Chemical group 0.000 claims description 4
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 3
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 3
• 125000005194 alkoxycarbonyloxy group Chemical group 0.000 claims description 3
• 125000006612 decyloxy group Chemical group 0.000 claims description 3
• 125000004440 haloalkylsulfinyl group Chemical group 0.000 claims description 3
• 125000000232 haloalkynyl group Chemical group 0.000 claims description 3
• 150000002923 oximes Chemical class 0.000 claims description 3
• HKOOXMFOFWEVGF-UHFFFAOYSA-N phenylhydrazine Chemical compound NNC1=CC=CC=C1 HKOOXMFOFWEVGF-UHFFFAOYSA-N 0.000 claims description 3
• 238000006467 substitution reaction Methods 0.000 claims description 3
• 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 claims description 2
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
• 229940067157 phenylhydrazine Drugs 0.000 claims description 2
• 125000004076 pyridyl group Chemical group 0.000 claims description 2
• 125000004354 sulfur functional group Chemical group 0.000 claims description 2
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 6
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 4
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 3
• 125000005843 halogen group Chemical group 0.000 claims 3
• 125000004149 thio group Chemical group *S* 0.000 claims 3
• SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims 2
• 125000006643 (C2-C6) haloalkenyl group Chemical group 0.000 claims 1
• HGUFODBRKLSHSI-UHFFFAOYSA-N 2,3,7,8-tetrachloro-dibenzo-p-dioxin Chemical compound O1C2=CC(Cl)=C(Cl)C=C2OC2=C1C=C(Cl)C(Cl)=C2 HGUFODBRKLSHSI-UHFFFAOYSA-N 0.000 claims 1
• ORMFXQGWVTZNRK-UHFFFAOYSA-N 2-(3-chloropyridin-2-yl)-5-(trifluoromethyl)pyrazole-3-carboxamide Chemical compound NC(=O)C1=CC(C(F)(F)F)=NN1C1=NC=CC=C1Cl ORMFXQGWVTZNRK-UHFFFAOYSA-N 0.000 claims 1
• 125000003277 amino group Chemical group 0.000 claims 1
• 125000005708 carbonyloxy group Chemical group [*:2]OC([*:1])=O 0.000 claims 1
• 150000001924 cycloalkanes Chemical class 0.000 claims 1
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
• PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims 1
• RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims 1
• 230000001850 reproductive effect Effects 0.000 claims 1
• 239000000460 chlorine Substances 0.000 description 213
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 42
• 239000002585 base Substances 0.000 description 39
• 241000196324 Embryophyta Species 0.000 description 38
• 239000003053 toxin Substances 0.000 description 37
• 231100000765 toxin Toxicity 0.000 description 37
• 108700012359 toxins Proteins 0.000 description 37
• 239000000126 substance Substances 0.000 description 36
• 230000000694 effects Effects 0.000 description 32
• 239000002253 acid Substances 0.000 description 25
• 240000008042 Zea mays Species 0.000 description 24
• 238000011161 development Methods 0.000 description 24
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 23
• 235000002017 Zea mays subsp mays Nutrition 0.000 description 23
• 108090000623 proteins and genes Proteins 0.000 description 22
• 241000238631 Hexapoda Species 0.000 description 20
• 239000002904 solvent Substances 0.000 description 19
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
• 125000004432 carbon atom Chemical group C* 0.000 description 17
• 238000006243 chemical reaction Methods 0.000 description 17
• 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 16
• 235000005822 corn Nutrition 0.000 description 16
• 238000012360 testing method Methods 0.000 description 16
• 235000018102 proteins Nutrition 0.000 description 15
• 102000004169 proteins and genes Human genes 0.000 description 15
• 239000011734 sodium Substances 0.000 description 15
• 229910052708 sodium Inorganic materials 0.000 description 15
• 150000001340 alkali metals Chemical class 0.000 description 14
• 239000002689 soil Substances 0.000 description 14
• 239000000243 solution Substances 0.000 description 14
• DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 13
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 13
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 13
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
• 229910052783 alkali metal Inorganic materials 0.000 description 12
• 150000002148 esters Chemical class 0.000 description 12
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
• 239000003085 diluting agent Substances 0.000 description 11
• 239000000843 powder Substances 0.000 description 11
• 229920000742 Cotton Polymers 0.000 description 10
• 241000219146 Gossypium Species 0.000 description 10
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
• 229910052784 alkaline earth metal Inorganic materials 0.000 description 10
• 239000000839 emulsion Substances 0.000 description 10
• 239000004009 herbicide Substances 0.000 description 10
• 229910052751 metal Inorganic materials 0.000 description 10
• 239000002184 metal Substances 0.000 description 10
• 238000002360 preparation method Methods 0.000 description 10
• 239000007787 solid Substances 0.000 description 10
• 239000007921 spray Substances 0.000 description 10
• 239000004094 surface-active agent Substances 0.000 description 10
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 9
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 8
• 239000003795 chemical substances by application Substances 0.000 description 8
• GGSUCNLOZRCGPQ-UHFFFAOYSA-N diethylaniline Chemical compound CCN(CC)C1=CC=CC=C1 GGSUCNLOZRCGPQ-UHFFFAOYSA-N 0.000 description 8
• 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 description 8
• 239000008187 granular material Substances 0.000 description 8
• 239000003112 inhibitor Substances 0.000 description 8
• VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 8
• 230000009467 reduction Effects 0.000 description 8
• LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 7
• OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 7
• 235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 description 7
• QGLZXHRNAYXIBU-WEVVVXLNSA-N aldicarb Chemical compound CNC(=O)O\N=C\C(C)(C)SC QGLZXHRNAYXIBU-WEVVVXLNSA-N 0.000 description 7
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• 239000003701 inert diluent Substances 0.000 description 7
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• 150000002576 ketones Chemical class 0.000 description 7
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• 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 7
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• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
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• 239000003153 chemical reaction reagent Substances 0.000 description 6
• 235000019439 ethyl acetate Nutrition 0.000 description 6
• 229910052740 iodine Inorganic materials 0.000 description 6
• NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 6
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• 229910052698 phosphorus Inorganic materials 0.000 description 6
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• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 5
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• 229910052794 bromium Inorganic materials 0.000 description 5
• 229910052799 carbon Inorganic materials 0.000 description 5
• 229910052801 chlorine Inorganic materials 0.000 description 5
• QLFZZSKTJWDQOS-YDBLARSUSA-N doramectin Chemical compound O1[C@@H](C)[C@H](O)[C@@H](OC)C[C@@H]1O[C@@H]1[C@@H](OC)C[C@H](O[C@@H]2C(=C/C[C@@H]3C[C@@H](C[C@@]4(O3)C=C[C@H](C)[C@@H](C3CCCCC3)O4)OC(=O)[C@@H]3C=C(C)[C@@H](O)[C@H]4OC\C([C@@]34O)=C/C=C/[C@@H]2C)/C)O[C@H]1C QLFZZSKTJWDQOS-YDBLARSUSA-N 0.000 description 5
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• 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 5
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• 239000011737 fluorine Substances 0.000 description 5
• 229910052731 fluorine Inorganic materials 0.000 description 5
• JLYXXMFPNIAWKQ-UHFFFAOYSA-N gamma-hexachlorocyclohexane Natural products ClC1C(Cl)C(Cl)C(Cl)C(Cl)C1Cl JLYXXMFPNIAWKQ-UHFFFAOYSA-N 0.000 description 5
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• 239000000376 reactant Substances 0.000 description 5
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• KUAZQDVKQLNFPE-UHFFFAOYSA-N thiram Chemical compound CN(C)C(=S)SSC(=S)N(C)C KUAZQDVKQLNFPE-UHFFFAOYSA-N 0.000 description 5
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• JTHMHWAHAKLCKT-UHFFFAOYSA-N 2,6-difluoro-n-[[4-(trifluoromethyl)phenyl]carbamoyl]benzamide Chemical compound FC1=CC=CC(F)=C1C(=O)NC(=O)NC1=CC=C(C(F)(F)F)C=C1 JTHMHWAHAKLCKT-UHFFFAOYSA-N 0.000 description 4
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• AZSNMRSAGSSBNP-UHFFFAOYSA-N 22,23-dihydroavermectin B1a Natural products C1CC(C)C(C(C)CC)OC21OC(CC=C(C)C(OC1OC(C)C(OC3OC(C)C(O)C(OC)C3)C(OC)C1)C(C)C=CC=C1C3(C(C(=O)O4)C=C(C)C(O)C3OC1)O)CC4C2 AZSNMRSAGSSBNP-UHFFFAOYSA-N 0.000 description 4
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• 150000001342 alkaline earth metals Chemical class 0.000 description 4
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• RIOXQFHNBCKOKP-UHFFFAOYSA-N benomyl Chemical compound C1=CC=C2N(C(=O)NCCCC)C(NC(=O)OC)=NC2=C1 RIOXQFHNBCKOKP-UHFFFAOYSA-N 0.000 description 4
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 4
• KXRPCFINVWWFHQ-UHFFFAOYSA-N cadusafos Chemical compound CCC(C)SP(=O)(OCC)SC(C)CC KXRPCFINVWWFHQ-UHFFFAOYSA-N 0.000 description 4
• 239000011575 calcium Substances 0.000 description 4
• 229910052791 calcium Inorganic materials 0.000 description 4
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