TW200522867A - Chemical compounds - Google Patents

Info

Publication number

TW200522867A

TW200522867A TW093137178A TW93137178A TW200522867A TW 200522867 A TW200522867 A TW 200522867A TW 093137178 A TW093137178 A TW 093137178A TW 93137178 A TW93137178 A TW 93137178A TW 200522867 A TW200522867 A TW 200522867A

Authority

TW

Taiwan

Prior art keywords

optionally substituted

alkyl

group

alkoxy

aryl

Prior art date

2003-12-12

Links

• Espacenet
• Global Dossier
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• 150000001875 compounds Chemical class 0.000 title claims abstract description 361
• 239000000203 mixture Substances 0.000 claims abstract description 71
• 229910052799 carbon Inorganic materials 0.000 claims abstract description 27
• 241000238631 Hexapoda Species 0.000 claims abstract description 15
• 241000244206 Nematoda Species 0.000 claims abstract description 12
• 150000003839 salts Chemical class 0.000 claims abstract description 12
• 229910052717 sulfur Inorganic materials 0.000 claims abstract description 11
• 241000237852 Mollusca Species 0.000 claims abstract description 9
• 150000001204 N-oxides Chemical class 0.000 claims abstract 3
• 125000000217 alkyl group Chemical group 0.000 claims description 257
• -1 optionally Chemical group 0.000 claims description 229
• 125000003545 alkoxy group Chemical group 0.000 claims description 113
• 125000001072 heteroaryl group Chemical group 0.000 claims description 113
• 125000003118 aryl group Chemical group 0.000 claims description 103
• 229910052736 halogen Inorganic materials 0.000 claims description 88
• 150000002367 halogens Chemical class 0.000 claims description 74
• 229910052739 hydrogen Inorganic materials 0.000 claims description 72
• 125000000623 heterocyclic group Chemical group 0.000 claims description 64
• 125000001188 haloalkyl group Chemical group 0.000 claims description 59
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 56
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 48
• 125000004438 haloalkoxy group Chemical group 0.000 claims description 47
• 125000005843 halogen group Chemical group 0.000 claims description 44
• 125000000304 alkynyl group Chemical group 0.000 claims description 39
• 239000001257 hydrogen Substances 0.000 claims description 39
• 125000003342 alkenyl group Chemical group 0.000 claims description 34
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 34
• NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims description 34
• 150000001412 amines Chemical class 0.000 claims description 32
• 125000004663 dialkyl amino group Chemical group 0.000 claims description 32
• 241000607479 Yersinia pestis Species 0.000 claims description 27
• 239000007789 gas Substances 0.000 claims description 27
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 27
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 26
• 238000000034 method Methods 0.000 claims description 24
• 150000002431 hydrogen Chemical group 0.000 claims description 23
• 125000005842 heteroatom Chemical group 0.000 claims description 22
• 125000003107 substituted aryl group Chemical group 0.000 claims description 22
• 125000001424 substituent group Chemical group 0.000 claims description 20
• 125000004104 aryloxy group Chemical group 0.000 claims description 19
• 125000005553 heteroaryloxy group Chemical group 0.000 claims description 19
• 229910052757 nitrogen Inorganic materials 0.000 claims description 19
• 125000004414 alkyl thio group Chemical group 0.000 claims description 18
• 238000006467 substitution reaction Methods 0.000 claims description 18
• 125000005415 substituted alkoxy group Chemical group 0.000 claims description 17
• 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 16
• JCXJVPUVTGWSNB-UHFFFAOYSA-N nitrogen dioxide Inorganic materials O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 claims description 16
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 15
• 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 14
• 125000000547 substituted alkyl group Chemical group 0.000 claims description 14
• 125000003282 alkyl amino group Chemical group 0.000 claims description 13
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 13
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 13
• 125000001960 7 membered carbocyclic group Chemical group 0.000 claims description 12
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 12
• 230000000749 insecticidal effect Effects 0.000 claims description 12
• 125000001054 5 membered carbocyclic group Chemical group 0.000 claims description 11
• 125000004008 6 membered carbocyclic group Chemical group 0.000 claims description 11
• 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 11
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 11
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 11
• 150000003254 radicals Chemical class 0.000 claims description 11
• 230000000895 acaricidal effect Effects 0.000 claims description 10
• 125000003277 amino group Chemical group 0.000 claims description 10
• 125000000392 cycloalkenyl group Chemical group 0.000 claims description 10
• 239000002689 soil Substances 0.000 claims description 10
• 241000238876 Acari Species 0.000 claims description 9
• 125000004432 carbon atom Chemical group C* 0.000 claims description 9
• 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 8
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 8
• 125000005129 aryl carbonyl group Chemical group 0.000 claims description 8
• 230000001069 nematicidal effect Effects 0.000 claims description 8
• 239000000126 substance Substances 0.000 claims description 8
• 150000001335 aliphatic alkanes Chemical class 0.000 claims description 7
• 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims description 6
• 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 6
• 125000004470 heterocyclooxy group Chemical group 0.000 claims description 6
• CPRRHERYRRXBRZ-SRVKXCTJSA-N methyl n-[(2s)-1-[[(2s)-1-hydroxy-3-[(3s)-2-oxopyrrolidin-3-yl]propan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]carbamate Chemical group COC(=O)N[C@@H](CC(C)C)C(=O)N[C@H](CO)C[C@@H]1CCNC1=O CPRRHERYRRXBRZ-SRVKXCTJSA-N 0.000 claims description 6
• MWUXSHHQAYIFBG-UHFFFAOYSA-N nitrogen oxide Inorganic materials O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 claims description 6
• 125000005017 substituted alkenyl group Chemical group 0.000 claims description 6
• 125000004426 substituted alkynyl group Chemical group 0.000 claims description 6
• 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 5
• 125000005110 aryl thio group Chemical group 0.000 claims description 5
• 125000004966 cyanoalkyl group Chemical group 0.000 claims description 5
• 125000005265 dialkylamine group Chemical group 0.000 claims description 5
• 125000002887 hydroxy group Chemical group [H]O* 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
• 229920006395 saturated elastomer Polymers 0.000 claims description 5
• 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 5
• 125000001845 4 membered carbocyclic group Chemical group 0.000 claims description 4
• 125000004429 atom Chemical group 0.000 claims description 4
• 125000004149 thio group Chemical group *S* 0.000 claims description 4
• PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 3
• 125000005090 alkenylcarbonyl group Chemical group 0.000 claims description 3
• 125000003302 alkenyloxy group Chemical group 0.000 claims description 3
• 125000005087 alkynylcarbonyl group Chemical group 0.000 claims description 3
• 125000005347 halocycloalkyl group Chemical group 0.000 claims description 3
• ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 3
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 2
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 2
• VEDTXTNSFWUXGQ-UHFFFAOYSA-N Carbophenothion Chemical group CCOP(=S)(OCC)SCSC1=CC=C(Cl)C=C1 VEDTXTNSFWUXGQ-UHFFFAOYSA-N 0.000 claims description 2
• OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical group NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 2
• 125000005092 alkenyloxycarbonyl group Chemical group 0.000 claims description 2
• 150000001345 alkine derivatives Chemical class 0.000 claims description 2
• 125000002355 alkine group Chemical group 0.000 claims description 2
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 2
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
• 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims 4
• 150000004820 halides Chemical class 0.000 claims 2
• 125000004043 oxo group Chemical group O=* 0.000 claims 2
• MTCFGRXMJLQNBG-REOHCLBHSA-N (2S)-2-Amino-3-hydroxypropansäure Chemical compound OC[C@H](N)C(O)=O MTCFGRXMJLQNBG-REOHCLBHSA-N 0.000 claims 1
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 1
• 102000016736 Cyclin Human genes 0.000 claims 1
• 108050006400 Cyclin Proteins 0.000 claims 1
• 241000282376 Panthera tigris Species 0.000 claims 1
• MTCFGRXMJLQNBG-UHFFFAOYSA-N Serine Natural products OCC(N)C(O)=O MTCFGRXMJLQNBG-UHFFFAOYSA-N 0.000 claims 1
• 150000003973 alkyl amines Chemical class 0.000 claims 1
• 125000005225 alkynyloxycarbonyl group Chemical group 0.000 claims 1
• 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims 1
• 125000005161 aryl oxy carbonyl group Chemical group 0.000 claims 1
• 229910052790 beryllium Inorganic materials 0.000 claims 1
• ATBAMAFKBVZNFJ-UHFFFAOYSA-N beryllium atom Chemical group [Be] ATBAMAFKBVZNFJ-UHFFFAOYSA-N 0.000 claims 1
• 235000010290 biphenyl Nutrition 0.000 claims 1
• 239000004305 biphenyl Substances 0.000 claims 1
• 125000006267 biphenyl group Chemical group 0.000 claims 1
• 125000004181 carboxyalkyl group Chemical group 0.000 claims 1
• 125000003901 ceryl 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])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])C([H])([H])[H] 0.000 claims 1
• 230000000295 complement effect Effects 0.000 claims 1
• 150000002012 dioxanes Chemical class 0.000 claims 1
• 125000003106 haloaryl group Chemical group 0.000 claims 1
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
• BQJCRHHNABKAKU-KBQPJGBKSA-N morphine Chemical group O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O BQJCRHHNABKAKU-KBQPJGBKSA-N 0.000 claims 1
• 238000007363 ring formation reaction Methods 0.000 claims 1
• RUPAXCPQAAOIPB-UHFFFAOYSA-N tert-butyl formate Chemical group CC(C)(C)OC=O RUPAXCPQAAOIPB-UHFFFAOYSA-N 0.000 claims 1
• 229910052760 oxygen Inorganic materials 0.000 abstract description 6
• 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 abstract description 2
• 125000000962 organic group Chemical group 0.000 abstract 1
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 141
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 66
• 150000007857 hydrazones Chemical class 0.000 description 63
• 239000002585 base Substances 0.000 description 35
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 30
• 239000000243 solution Substances 0.000 description 28
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 25
• 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 25
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 23
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 21
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 21
• ATPNEAQEWYMEJG-UHFFFAOYSA-N 1-propyl-9h-fluorene Chemical compound C1C2=CC=CC=C2C2=C1C(CCC)=CC=C2 ATPNEAQEWYMEJG-UHFFFAOYSA-N 0.000 description 17
• 239000007788 liquid Substances 0.000 description 17
• 229910052698 phosphorus Inorganic materials 0.000 description 17
• 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 16
• XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 14
• 238000006243 chemical reaction Methods 0.000 description 14
• 239000000843 powder Substances 0.000 description 14
• 238000002360 preparation method Methods 0.000 description 14
• UKJLNMAFNRKWGR-UHFFFAOYSA-N cyclohexatrienamine Chemical group NC1=CC=C=C[CH]1 UKJLNMAFNRKWGR-UHFFFAOYSA-N 0.000 description 13
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
• 239000010949 copper Substances 0.000 description 12
• 238000009472 formulation Methods 0.000 description 12
• 239000002904 solvent Substances 0.000 description 12
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
• 239000003480 eluent Substances 0.000 description 11
• 239000003960 organic solvent Substances 0.000 description 11
• 125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 description 10
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 10
• XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 10
• 241000196324 Embryophyta Species 0.000 description 10
• RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 10
• 239000008187 granular material Substances 0.000 description 10
• 238000010898 silica gel chromatography Methods 0.000 description 10
• 239000007787 solid Substances 0.000 description 10
• 125000003003 spiro group Chemical group 0.000 description 10
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 9
• 239000002253 acid Substances 0.000 description 9
• 239000004480 active ingredient Substances 0.000 description 9
• 239000000047 product Substances 0.000 description 9
• 239000011541 reaction mixture Substances 0.000 description 9
• 229910052938 sodium sulfate Inorganic materials 0.000 description 9
• 235000011152 sodium sulphate Nutrition 0.000 description 9
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 9
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
• 239000003795 chemical substances by application Substances 0.000 description 8
• 235000019441 ethanol Nutrition 0.000 description 8
• 239000004530 micro-emulsion Substances 0.000 description 8
• 229910052786 argon Inorganic materials 0.000 description 7
• 239000003921 oil Substances 0.000 description 7
• 238000011282 treatment Methods 0.000 description 7
• CVICEEPAFUYBJG-UHFFFAOYSA-N 5-chloro-2,2-difluoro-1,3-benzodioxole Chemical group C1=C(Cl)C=C2OC(F)(F)OC2=C1 CVICEEPAFUYBJG-UHFFFAOYSA-N 0.000 description 6
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
• 241000255925 Diptera Species 0.000 description 6
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 6
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 6
• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 6
• 239000012267 brine Substances 0.000 description 6
• 239000004490 capsule suspension Substances 0.000 description 6
• 239000003638 chemical reducing agent Substances 0.000 description 6
• 230000000694 effects Effects 0.000 description 6
• 239000000839 emulsion Substances 0.000 description 6
• VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 6
• 238000002156 mixing Methods 0.000 description 6
• 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 6
• DLRJIFUOBPOJNS-UHFFFAOYSA-N phenetole Chemical compound CCOC1=CC=CC=C1 DLRJIFUOBPOJNS-UHFFFAOYSA-N 0.000 description 6
• 235000021391 short chain fatty acids Nutrition 0.000 description 6
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 6
• 239000004575 stone Substances 0.000 description 6
• 239000004094 surface-active agent Substances 0.000 description 6
• RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 6
• 241000256602 Isoptera Species 0.000 description 5
• 241000500437 Plutella xylostella Species 0.000 description 5
• 241000256250 Spodoptera littoralis Species 0.000 description 5
• 239000000654 additive Substances 0.000 description 5
• 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 5
• 150000001721 carbon Chemical group 0.000 description 5
• 239000003153 chemical reaction reagent Substances 0.000 description 5
• 239000002270 dispersing agent Substances 0.000 description 5
• 150000002148 esters Chemical class 0.000 description 5
• 239000003337 fertilizer Substances 0.000 description 5
• 239000002917 insecticide Substances 0.000 description 5
• 238000001819 mass spectrum Methods 0.000 description 5
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 5
• 235000019198 oils Nutrition 0.000 description 5
• 239000001301 oxygen Substances 0.000 description 5
• 125000000714 pyrimidinyl group Chemical group 0.000 description 5
• 239000007921 spray Substances 0.000 description 5
• RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium Chemical compound [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 description 5
• 239000011593 sulfur Substances 0.000 description 5
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 4
• 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 4
• 241000256118 Aedes aegypti Species 0.000 description 4
• VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 4
• BDAGIHXWWSANSR-UHFFFAOYSA-N Formic acid Chemical compound OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
• 241000237858 Gastropoda Species 0.000 description 4
• 241000258937 Hemiptera Species 0.000 description 4
• 240000007594 Oryza sativa Species 0.000 description 4
• 235000007164 Oryza sativa Nutrition 0.000 description 4
• NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
• CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
• 239000000642 acaricide Substances 0.000 description 4
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
• 125000002837 carbocyclic group Chemical group 0.000 description 4
• 239000003085 diluting agent Substances 0.000 description 4
• 239000000194 fatty acid Substances 0.000 description 4
• 125000001153 fluoro group Chemical group F* 0.000 description 4
• 230000002013 molluscicidal effect Effects 0.000 description 4
• 239000012044 organic layer Substances 0.000 description 4
• 239000000575 pesticide Substances 0.000 description 4
• 235000009566 rice Nutrition 0.000 description 4
• 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 4
• 239000000725 suspension Substances 0.000 description 4
• 239000012085 test solution Substances 0.000 description 4
• HJUGFYREWKUQJT-UHFFFAOYSA-N tetrabromomethane Chemical compound BrC(Br)(Br)Br HJUGFYREWKUQJT-UHFFFAOYSA-N 0.000 description 4
• HIOZPFGGCXEPAP-UHFFFAOYSA-N 1-propylpyrene Chemical compound C1=C2C(CCC)=CC=C(C=C3)C2=C2C3=CC=CC2=C1 HIOZPFGGCXEPAP-UHFFFAOYSA-N 0.000 description 3
• 125000006189 4-phenyl benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
• 241001674044 Blattodea Species 0.000 description 3
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 description 3
• RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 3
• 229920000742 Cotton Polymers 0.000 description 3
• IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 3
• 241000219146 Gossypium Species 0.000 description 3
• 241001147381 Helicoverpa armigera Species 0.000 description 3
• 241000255967 Helicoverpa zea Species 0.000 description 3
• KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
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