JP2005516037A

JP2005516037A - ジアミド無脊椎有害生物防除剤

ジアミド無脊椎有害生物防除剤 Download PDF

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Publication number: JP2005516037A
Authority: JP; Japan
Prior art keywords: halogen; ring; independently; alkyl; optionally substituted
Prior art date: 2002-01-22
Legal status : Withdrawn

Application number

JP2003562100A

Other languages

English (en)

Japanese (ja)

Other versions

JP2005516037A5 (https=

Inventor

クラーク，デイビツド・アラン

Current Assignee

EIDP Inc

Original Assignee

EI Du Pont de Nemours and Co

Priority date

2002-01-22

Filing date

2003-01-13

Publication date

2005-06-02

2003-01-13 Application filed by EI Du Pont de Nemours and Co filed Critical EI Du Pont de Nemours and Co

2005-06-02 Publication of JP2005516037A publication Critical patent/JP2005516037A/ja

2006-01-05 Publication of JP2005516037A5 publication Critical patent/JP2005516037A5/ja

Status Withdrawn legal-status Critical Current

Links

241000607479 Yersinia pestis Species 0.000 title claims abstract description 62
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 title 1
150000001875 compounds Chemical class 0.000 claims abstract description 186
239000000203 mixture Substances 0.000 claims abstract description 73
229910052799 carbon Inorganic materials 0.000 claims abstract description 50
238000000034 method Methods 0.000 claims abstract description 34
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 29
125000000623 heterocyclic group Chemical group 0.000 claims abstract description 21
150000003839 salts Chemical class 0.000 claims abstract description 20
150000001204 N-oxides Chemical class 0.000 claims abstract description 19
229910052757 nitrogen Inorganic materials 0.000 claims abstract description 19
125000004122 cyclic group Chemical group 0.000 claims abstract description 17
125000003118 aryl group Chemical group 0.000 claims abstract description 15
229910052717 sulfur Inorganic materials 0.000 claims abstract description 13
229910052760 oxygen Inorganic materials 0.000 claims abstract description 12
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 7
-1 C 1 -C 4 alkoxy Chemical group 0.000 claims description 81
229910052736 halogen Inorganic materials 0.000 claims description 66
150000002367 halogens Chemical class 0.000 claims description 66
125000001424 substituent group Chemical group 0.000 claims description 45
229910052739 hydrogen Inorganic materials 0.000 claims description 27
239000007787 solid Substances 0.000 claims description 25
UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 claims description 24
125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 23
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 23
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 17
239000003085 diluting agent Substances 0.000 claims description 15
125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims description 14
125000000217 alkyl group Chemical group 0.000 claims description 13
239000003795 chemical substances by application Substances 0.000 claims description 13
125000004768 (C1-C4) alkylsulfinyl group Chemical group 0.000 claims description 12
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 12
125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims description 10
125000004771 (C1-C4) haloalkylsulfinyl group Chemical group 0.000 claims description 10
125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 10
125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 10
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 10
239000004094 surface-active agent Substances 0.000 claims description 10
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 9
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 8
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 8
125000000262 haloalkenyl group Chemical group 0.000 claims description 8
239000007788 liquid Substances 0.000 claims description 8
125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 7
125000003545 alkoxy group Chemical group 0.000 claims description 7
229910052801 chlorine Inorganic materials 0.000 claims description 7
125000004663 dialkyl amino group Chemical group 0.000 claims description 7
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
229910052794 bromium Inorganic materials 0.000 claims description 6
125000004356 hydroxy functional group Chemical group O* 0.000 claims description 6
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 6
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 6
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 6
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 5
125000000753 cycloalkyl group Chemical group 0.000 claims description 5
125000004473 dialkylaminocarbonyl group Chemical group 0.000 claims description 5
229910052740 iodine Inorganic materials 0.000 claims description 5
239000011593 sulfur Substances 0.000 claims description 5
125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 4
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 4
WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 3
125000003282 alkyl amino group Chemical group 0.000 claims description 3
125000004429 atom Chemical group 0.000 claims description 3
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 3
150000001721 carbon Chemical group 0.000 claims description 3
229910052731 fluorine Inorganic materials 0.000 claims description 3
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-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
XZWNGLCLCKSHQD-UHFFFAOYSA-N 5-bromo-2-(3-chloropyridin-2-yl)-n-[2-methyl-6-(propan-2-ylcarbamoyl)cyclohexen-1-yl]pyrazole-3-carboxamide Chemical compound CC(C)NC(=O)C1CCCC(C)=C1NC(=O)C1=CC(Br)=NN1C1=NC=CC=C1Cl XZWNGLCLCKSHQD-UHFFFAOYSA-N 0.000 claims description 2
125000002853 C1-C4 hydroxyalkyl group Chemical group 0.000 claims description 2
229910002091 carbon monoxide Inorganic materials 0.000 claims description 2
125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 2
125000006310 cycloalkyl amino group Chemical group 0.000 claims description 2
125000004430 oxygen atom Chemical group O* 0.000 claims description 2
125000000714 pyrimidinyl group Chemical group 0.000 claims description 2
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
150000003852 triazoles Chemical class 0.000 claims description 2
239000000126 substance Substances 0.000 abstract description 8
239000012681 biocontrol agent Substances 0.000 abstract 1
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 45
239000000243 solution Substances 0.000 description 32
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 30
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 30
239000000047 product Substances 0.000 description 29
238000012360 testing method Methods 0.000 description 24
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 21
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
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238000002360 preparation method Methods 0.000 description 17
241000254173 Coleoptera Species 0.000 description 16
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 15
238000009472 formulation Methods 0.000 description 15
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 14
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
241001124076 Aphididae Species 0.000 description 13
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 12
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 11
239000002253 acid Substances 0.000 description 11
238000006243 chemical reaction Methods 0.000 description 11
241000238876 Acari Species 0.000 description 10
241000238631 Hexapoda Species 0.000 description 10
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
125000004435 hydrogen atom Chemical group [H]* 0.000 description 10
239000011541 reaction mixture Substances 0.000 description 10
241000193388 Bacillus thuringiensis Species 0.000 description 9
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
229940097012 bacillus thuringiensis Drugs 0.000 description 9
230000006378 damage Effects 0.000 description 9
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235000019198 oils Nutrition 0.000 description 9
238000003756 stirring Methods 0.000 description 9
241000244206 Nematoda Species 0.000 description 8
239000004480 active ingredient Substances 0.000 description 8
NYPJDWWKZLNGGM-UHFFFAOYSA-N fenvalerate Aalpha Natural products 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 7
229910052943 magnesium sulfate Inorganic materials 0.000 description 7
235000019341 magnesium sulphate Nutrition 0.000 description 7
238000005507 spraying Methods 0.000 description 7
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
241000239290 Araneae Species 0.000 description 6
0 CCCCCCC(*(CC)*1CC1)*(C)(CCCC)C1(CB1)N(*)* Chemical compound CCCCCCC(*(CC)*1CC1)*(C)(CCCC)C1(CB1)N(*)* 0.000 description 6
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
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YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
150000001412 amines Chemical class 0.000 description 6
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230000000694 effects Effects 0.000 description 6
235000013305 food Nutrition 0.000 description 6
239000008187 granular material Substances 0.000 description 6
ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 6
CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 6
229910000027 potassium carbonate Inorganic materials 0.000 description 6
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125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
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239000000725 suspension Substances 0.000 description 5
241001674044 Blattodea Species 0.000 description 4
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
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MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
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